OA20567A - Herbicidal compositions. - Google Patents
Herbicidal compositions. Download PDFInfo
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- OA20567A OA20567A OA1202100603 OA20567A OA 20567 A OA20567 A OA 20567A OA 1202100603 OA1202100603 OA 1202100603 OA 20567 A OA20567 A OA 20567A
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Abstract
Herbicidal composition. The present invention provides compositions comprising herbicidally active compounds (A) and (B), wherein (A) represents one or more compounds of the general formula (I) or agrochemically acceptable salts thereof [component (A)], and (B) represents one or more herbicides [component (B)]. The application further relates to a method and to the use of the herbicidal composition of the invention for controlling harmful plants or for regulating growth.
Description
Herbicidal compositions
Description
The invention is in the technical field of crop protection products that can be used to counter unwanted plant growth on uncultivated land, for préparation for seeding or in plant crops, and comprise a combination of at least two herbicides as herbicidally active ingrédients, wherein the compositions comprise herbicidally active compounds (A) and (B), in which (A) represents one or more compounds of the general formula (I) or agrochemically acceptable salts thereof [herbicides (A) or component (A)] and 10 (B) represents one or more herbicides-(component B).
Compounds from the structure class of the 3-phenylisoxazoline-5-carboxamides are known as herbicides (see, for example, WO2012/130798 A). The compounds are effective against a broad spectrum of harmful plants when applied by the pre-emergence method or else by the post-emergence method, with the possibility of non-selective use for control of unwanted plant growth or sélective use in plant crops.
The efficacy of these herbicides against harmful plants is at a high level, but generalîy dépends on the application rate, the form of the respective préparation, the spectrum of harmful plants, the harmful plants to be controlled in each case, climate and soif conditions, etc. A further criterion is the duration of action or the rate of dégradation of the herbicide. Other considérations, as the case may be, are changes in the susceptibility of harmful plants which may occur on prolotiged use of the herbicides or in a geographically 20 restricted manner. Compensation for losses in action in the case of individual plants by higher application rates of the herbicides îs only possible to a limited degree, for example because this frequently worsens the selectivity of the herbicides or because there is no improvement in action, even in the case of a higher application rate. There is generalîy need for methods of achieving herbicidal action with a lower application rate of active ingrédients. A lower application rate not only reduces the amount of active ingrédient required for the application but generalîy also reduces the amount of formulation auxiliaries needed. Both reduce économie expenditure and improve the environmental compatîbility of the herbicide treatment.
One way of improving the application profile of a herbicide may be to combine the active ingrédient with one or more other active ingrédients which contribute the desired additional properties. However, in the 30 case of combined application of two or more active ingrédients, it is not uncommon for there to be phenomena of physical and biological incompatibility, for example lack of stability in a coformulation, décomposition of an active ingrédient and/or antagonism of the active ingrédients. What are desired, by contrast, are combinations of active ingrédients having a favourable profile of activity, high stability and ideally an unexpectedly synergistically enhanced activity which allows the application rate to be reduced 35 compared to the individual application of the active ingrédients to be combined.
It is an object of the présent invention to provide alternative or advantageous herbicidal compositions that hâve a good profile of bioiogical use and hâve as many as possible of the abovementioned désirable favourable properties.
Ii has now been found that, surprisingly, this object can be achieved by using a composition comprising 5 herbicidally active compounds (A) and (B), wherein (A) represents one or more compounds of the general formula (I) or agrochemically acceptable salts thereof [component (A)] and (B) represents one or more herbicides [component (B)] selected from the group of the active herbicidal ingrédients (Bl) to (Bll). The compositions of the invention internet in a particularly favourable manner, for example when they are used to control unwanted plant growth in crop plants such as wheat (hard and soft wheat), maize, soya, 10 sugarbeet, sugarcane, cotton, rice, beans (for example, bush beans and broad beans), flax, barley, oats, rye, triticale, potato and millet/sorghum, uncultivated land, pastureland and areas of grass/lawn and plantation crops.
The présent invention thus provides compositions comprising herbicidally active compounds (A) and (B), where (A) represents one or more compounds of the general formula (I) or agrochemically acceptable salts thereof [component (A)],
in which
G is a group of the formula OR4 or NRllR12;
R1 and R2 are each independently hydrogen, halogen or cyano, or are (CrQj-alkyi or (CrCfi-alkoxy, each substituted by m radicals from the group consisting of halogen and cyano;
R-* is cyano or fluorine, or is (Ci-c5)-alkyl, (Cj-Cq-cycloalkyl, (C2-C5)-alkenyl, (C2-C5)-alkynyl or (Ci-C5)-alkoxy, each substituted by m radicals from the group consisting of halogen, cyano, (Ci-Cq-alkoxy and 30 hydroxy;
R4 is hydrogen, or is (Ci-Ci2)-alkyl, (Cj-Cîj-cycIoalkyl, (Ca-Cvj-cycloalkyl^Ci-Csj-alkyl, (Cz-Csj-alkenyl, (CsC^-cycloalkenyl or (Ci-Ctô-alkynyk each substituted by m radicals from the group consistîng of halogen, cyano, (Ci-Cô)-alkoxy, hydroxy and aryl;
Y is oxygen or sulfur;
W is oxygen or sulfur;
Z represents a monounsaturated cyclopentane ring substituted by k radicals from the group of R10,
where the arrow in each case represents a bond to the C-W group in the formula (I);
R!ü is halogen, cyano or CO2R7, or is (CrCïj-alkyl or (Ci-QJ-alkoxy, each substituted by m radicals from the group consistîng of fluorine and chlorine;
R11, R12 are each îndependently hydrogen, cyano, OR7, S(O)nRs, SO2NR6R7, CO2R8, CONR6R8, COR6, NR6RS, NRfiCOR8, NR6CONR5R8, NRfiCO2R8, NR6SO2R8, NR6SO2NR6R8, C(RÛ)=NORB, optionally substituted aryl, optionally substituted heteroaryl or optionally substituted heterocyclyl, or are (Ci-Ci2)-alkyl, (Ca-Csj-cycloalkyl, (C3-C7)-cycloalkyl-(Ci-C7)-alkyl, (C2-C12)alkenyl, (Cs-Cvj-cycloalkenyl or (C2-Ci2)-alkynyl, each substituted by m radicals from the group consistîng of halogen, cyano, nitro, OR7, S(O)nR5, SO2NR6R7, CO2R8, CONR6R8, COR6, NR6R8, NR6COR8, NR6CONR8R8, NRCO2RS, NR6SO2R8, NR6SO2NR6R8, C(R6)=NOR8, optionally substituted aryl, optionally substituted heteroaryl and optionally substituted heterocyclyl, or
R11 and R12 together with the nitrogen atom to which they are bonded form a saturated or partly or fully unsaturated five-, six- or seven-membered ring which îs optionally mono- to hexasubstituted by radicals from the group consisting of halogen, cyano, nitro, (Cj-Ch)alky!, halo-(Ci-C6)-alkyl, oxo, OR7, S(O)„R5, SO2NR6R7, CO2R8, CONR6R8, COR6,
NR6R8, NR6COR8, NR6CONR8Rs, NR6CO2R8, NRf’SO2R , NR6SO2NR6R8 and C(RÛ)=NORK and which, in addition to that nitrogen atom, contains r carbon atoms, o oxygen atoms, p sulfur atoms and q éléments from the group consisting of NR7 and NCOR7 as ring atoms;
X2, X4 and X6 are each independently hydrogen, halogen or cyano, or are (Ci-C2)-alkyl, in each case substituted by m radicals from the group consisting of fluorine, chlorine, bromine and (Ci-C2)-alkoxy;
X'1 and X5 are each independently hydrogen, fluorine, chlorine, bromine, iodine, hydroxy, cyano, nitro, S(O)eR6 or CO2R7, or are (Ci-C3)-alkyl, (CrC3)-alkoxy, (Cj-C^-cycloalkyl, (C2-C3)-alkenyl or (C2-C3)alkynyl, each substituted by m radicals from the group consisting of fluorine, chlorine and bromine;
R5 is (Ci-Cs)-alkyl, (C3-Cfi)-cydoalkyl or aryl, each substituted by m radicals from the group consisting of halogen, cyano and hydroxy;
R6 is hydrogen or R5;
R7 is hydrogen, or is (Ci-GO-alkyl, (C3-C6)-cycloalkyl, (Cj-C^alkenyi or (C3-C4)-alkynyl, each substituted by m radicals from the group consisting of halogen, cyano and (C]-C2)-alkoxy;
R8 is hydrogen, or îs (Ci-Cs)-alkyl, (Cj-C^-cycloalkyl, (C3-Cs)-alkenyl or (C3-C8)-alkynyl, each substituted by m radicals from the group consisting of halogen, cyano and (CrC2)-alkoxy;
the index k is 0, i or 2; where, when k > 1, R10 may independently be the same or different;
the index m is 0, 1, 2, 3, 4 or 5;
the index n is 0,1 or 2;
the index o is 0, 1 or 2;
the index p is 0 or 1;
the index q is 0 or 1; and the index r is 3, 4, 5 or 6.
and (B) represents one or more herbicides [component (B)] from the group of the active herbicidal ingrédients (Bl) to (Bll), in which (Bl) represents active herbicidal ingrédients from the group of the 1,3-diketo compounds selected from
| (Bl.l) | alloxydim, | (CAS 55634-91-8), (CAS 55635-13-7) |
| (B1.2) | bicyclopyrone, | (CAS 352010-68-5) |
| (B1.3) | butroxydim. | (CAS 138164-12-2) |
| (B 1.4) | clethodim. | (CAS 99129-21-2) |
| (B1.5) | cycloxydim, | (CAS 101205-02-1) |
| (B1.6) | fenquinotrione, | (CAS 1342891-70-6) |
| (B1.7) | mesotrione, | (CAS 104206-82-8) |
| (B 1.8) | pinoxaden, | (CAS 243973-20-8) |
| (B1.9) | profoxydim, | (CAS 139001-49-3) |
| (B1.10) | sethoxydim. | (CAS 74051-80-2) |
| (Bl.ll) | sulcotrione, | (CAS 99105-77-8) |
| (B1.12) | SYP-9121 | (CAS 1976053-87-8) |
| (B1.13) | tefuryltrione. | (CAS 473278-76-1) |
| (B1.14) | tembotrione, | (CAS 335104-84-2) |
| (B1.15) | tepraloxydim. | (CAS 149979-41-9) |
| (Bl.l 6) | tralkoxydim. | (CAS 87820-88-0) |
| (B1.17) | Y13161, | (CAS 1639426-14-4) |
| (Bl.l 8) | Y13287; | (CAS 1639426-42-8) |
• (B2) represents active herbicidai ingrédients from the group of the (sulfon)amides selected from
| (B2.1) | acetochlor, | |
| (B2.2) | alachlor, | (CAS 15972-60-8) |
| (B2.3) | amidosulfuron, | (CAS 120923-37-7) |
| (B2.4) | asulam, | (CAS 3337-71-1) (CAS 14089-43-1), (CAS 2302-17-2) |
| (B2.5) | azimsulfuron, | (CAS 120162-55-2) |
| (B2.6) | beflubutamid, | (CAS 113614-08-7), (CAS 113614-09-8) |
| (B2.7) | bensulfuron, | (CAS 83055-99-6), (CAS 83055-99-6) |
| (B2.8) | butachlor. | (CAS 23184-66-99) |
| (B2.9) | carbetamide, | (CAS 16118-49-3) |
| (B2.10) | chlorimuron, | (CAS 99283-00-8), (CAS 90982-32-4), |
| (B2.ll) | chlorpropham. | (CAS 101-21-3) |
| (B2.12) | chlorsulfuron, | (CAS 64902-72-3) |
| (B2.13) | cinosulfuron. | (CAS 94593-91-6) |
| (B2.14) | cloransulam. | (CAS159518-97-5), (CAS 147150-35-4) |
| (B2.15) | cyclosulfamuron. | (CAS 136849-15-5) |
| (B2.16) | desmedipliam, | (CAS 13684-56-5) |
| (B2.17) | diclosulam, | (CAS 145701-21-9) |
| (B2.18) | diflufenican, | (CAS 83164-33-4) |
| (B2.19) | dimethachlor, | (CAS 50563-36-5) |
| (B2.20) | dimethenamid, | (CAS 87674-68-8), (CAS 163515-14-8) |
| (B2.21) | esprocarb | (CAS 85785-20-2) |
| (B2.22) | ethametsulfuron, | (CAS 111353-84-5), (CAS 97780-06-8) |
| (B2.23) | ethoxysulfuron. | (CAS 126801-58-9) |
| (B2.24) | flazasulfuron. | (CAS 104040-78-0) |
| (B2.25) | florasulam, | (CAS 145701-23-1) |
| (B2.26) | flucarbazone. | (CAS 145026-88-6 ), (CAS 181274-17-9) |
| (B2.27) | flucetosulfuron, | (CAS 412928-75-7) |
| (B2.28) | flufenacet, | (CAS 142459-58-3) |
| (B2.29) | flumetsulam. | (CAS 98967-40-9) |
| (B2.30) | flupyrsulfuron, | (CAS 150315-10-9), (CAS 144740-53-4), (CAS 144740-54-5) |
| (B2.31) | foramsulfuron, | (CAS 173159-57-4) |
| (B2.32) | halosulfuron. | (CAS 135397-30-7), (CAS 100784-20-1) |
| (B2.33) | imazosulfuron, | (CAS 122548-33-8) |
| (B2.34) | io do sulfura η, | (CAS 185119-76-0), (CAS 144550-06-1), (CAS 144550-36-7) |
| (B2.35) | ipfencarbazoiie, | (CAS 212201-70-2) |
| (B2.36) | mefenacet. | (CAS 73250-68-7) |
| (B2.37) | mesosuifuron. | (CAS 400852-66-6), (CAS 208465-21-8) |
| (B2.38) | metazachlor, | (CAS 67129-08-2) |
| (B2.39) | metazosulfuron, | (CAS 868680-84-6) |
| (B2.40) | metolachlor, | (CAS 51218-45-2) |
| (B2.41) | metosulam. | (CAS 139528-85-1) |
| (B2.42) | metsuifuron. | (CAS 79510-48-8), (CAS 74223-64-6) |
| (B2.43) | nicosulfuron, | (CAS 111991-09-4) |
| (B2.44) | orthosu Ifamuron, | (CAS 213464-77-8) |
| (B2.45) | oxasulfuran. | (CAS 144651-06-9) |
| (B2.46) | penoxsulam, | (CAS 219714-96-2) |
| (B2.47) | pethoxamide, | (CAS 106700-29-2) |
| (B2.48) | phenmedipham, | (CAS 13684-63-4) |
| (B2.49) | picolinafen, | (CAS 137641-05-5) |
| (B2.50) | pretilachlor, | (CAS 51218-49-6) |
| (B2.51) | prîmisulfuron. | (CAS 113036-87-6), (CAS 86209-51-0) |
| (B2.52) | propachlor, | (CAS 1918-16-7) |
| (B2.53) | propanil. | (CAS 709-98-8) |
| (B2.54) | propham, | (CAS 122-42-9) |
| (B2.55) | propisochlor. | (CAS 86763-47-5) |
| (B2.56) | propoxycarbazone, | (CAS 145026-81-9), (CAS 181274-15-7) |
| (B2.57) | p ropy risu 1 f u ron, | (CAS 570415-88-2) |
| (B2.58) | propyzamide, | (CAS 23950-5 8-5) |
| (B2.59) | prosulfocarb. | (CAS 52888-80-9) |
| (B2.60) | prosulfuron, | (CAS 94125-34-5) |
| (B2.61) | pyrazosulfuron. | (CAS 98389-04-9), (CAS 93697-74-6) |
| (B2.62) | pyroxsulam, | (CAS 422556-08-9) |
| (B2.63) | rimsulfuron, | (CAS 122931-48-0) |
| (B2.64) | S-metolachlor, | (CAS 87392-12-9) |
| (B2.65) | sulfometuron, | (CAS 74223-56-6), (CAS 74222-97-2), (CAS 144651-06-9) |
| (B2.66) | sulfosulfuron, | (CAS 141776-32-1) |
| (B2.67) | thenylchlor, | (CAS 96491-05-3) |
| (B2.68) | thiencarbazone. | (CAS 936331-72-5), (CAS 317815-83-1) |
| (B2.69) | thifensulfuron, | (CAS 79277-67-1), (CAS 79277-27-3) |
| (B2.70) | tri-allate, | (CAS 2303-17-5) |
| (B2.71) | triasulfuron. | (CAS 82097-50-5) |
| (B2.72) | tribenuron, | (CAS 106040-48-6), (CAS 101200-48-0) |
| (B2.73) | trifloxysulfuron. | (CAS 145099-21-4, (CAS 199119-58-9) |
| (B2.74) | triflusulfuron, | (CAS 135990-29-3), (CAS 126535-15-7) |
| (B2.75) | tritosulfuron. | (CAS 142469-14-5) |
| (B2.76) | esprocarb, | (CAS 85785-20-2) |
| (B2.77) | profluazol, | (CAS 190314-43-3) |
| (B2.78) | tri-allate; | (CAS 2303-17-5) |
| (B3) represents active herbicidal ingrédients from the group of the aryl nitriles selected from | ||
| (B3.1) | bromoxynil, | (CAS 1689-84-5) (CAS 3861-41-4), (CAS 56634- |
| 95-8), (CAS 1689-99-2), (CAS 2961-68-4) | ||
| (B3.2) | chlorthiamid, | (CAS 1918-13-4) |
| (B3.3) | dichlobenil. | (CAS 1194-65-6) |
| (B3.4) | ioxynil, | (CAS 1689-83-4), (CAS 2961-61-7), (CAS 3861- |
| 47-0), (CAS 2961-62-8) | ||
| (B3.5) | pyraclonil; | (CAS 158353-15-2) |
| (B4) represents active herbicidal ingrédients from the group of the azoles selected from | ||
| (B4.1) | amicarbazone. |
| (B4.2) amitrole, (B4.3) azafenîdin, (B4.4) benzofenap, (B4.5) benzuofucaotong, (B4.6) biscarfentrazone, (B4.7) cafenstrole, (B4.8) carfentrazone, (B4.9) fentrazamîde, (B4.10) imazamethabenz, (B4.ll) imazamox, (B4.12) imazapic, (B4.13) imazapyr, (B4.14) imazaquin, (B4.15) imazethapyr, | (CAS 61-82-5) (CAS 68049-83-2) (CAS 82692-44-2) (CAS 1992017-55-6) (CAS 1622908-18-2) (CAS 125306-83-4) (CAS 128621-72-7), (CAS128639-02-1) (CAS 158237-07-1) (CAS 100728-84-5), (CAS 81405-85-8) (CAS 114311-32-9), (CAS 247057-22-3) (CAS 104098-48-8), (CAS 115136-53-3) (CAS 81334-34-1), (CAS 81510-83-0) (CAS 81335-37-7), (CAS 81335-47-9), (CAS 81335-43-5), (CAS 81335-46-8) (CAS 81335-77-5), (CAS 101917-66-2) |
| (B4.16) | isouron, | (CAS 55861-78-4) |
| (B4.17) | isoxaben, | (CAS 82558-50-7) |
| (B4.18) | isoxaflutole. | (CAS 141112-29-0) |
| (B4.19) | oxadiargyl, | (CAS 39807-15-3) |
| (B4.20) | oxadiazon. | (CAS 19666-30-9) |
| (B4.21) | pyraflufen, | (CAS 129630-17-7), (CAS 129630-19-9) |
| (B4.22) | pyrasulfotole, | (CAS 365400-11-9) |
| (B4.23) | pyrazolynate. | (CAS 58011-68-0) |
| (B4.24) | pyrazoxyfen, | (CAS 71561-11-0) |
| (B4.25) | pyroxasulfone. | (CAS 447399-55-5) |
| (B4.26) | sulfentrazone, | (CAS 122836-35-5) |
| (B4.27) | tolpyralate, | (CAS 1101132-67-5) |
| (B4.28) | topramezone. | (CAS 210631-68-8) |
| (B4.29) | triazolesulcotrione (QYR-301), | (CAS 1911613-97-2) |
| (B4.30) | QYM-201, | (CAS 1855925-45-1) |
| (B4.31) | bencarbazone, | (CAS 173980-17-1) |
| (B4.32) | fluazolate, | (CAS 174514-07-9) |
| (B4.33) | flupoxam, | (CAS 119126-15-7) |
| (B4.34) | isoxachlortole; | (CAS 141112-06-3) |
(B5) représente further active herbicidal ingrédients selected from
| (B5.1) | aminocyclopyrachlor, | (CAS 858956-08-8), (CAS 858954-83-3), (CAS 858956-35-1) |
| (B5.2) | aminopyralîd, | (CAS 150114-71-9), (CAS 566191-87-5), (CAS 566191-89-7) |
| (B5.3) | benazolin-ethyl, | (CAS 3813-05-6), (CAS 38561-76-1), (CAS 25059-80-7), (CAS 67338-65-2) |
| (B5.4) | benfluralin, | (CAS 1861-40-1) |
| (B5.5) | bentazone, | (CAS 25057-89-0), (CAS 50723-80-3) |
| (B5.6) | benzobicyclon, | (CAS 156963-66-5) |
| (B5.7) | bixlozone, | (CAS 81777-95-9) |
| (B5.8) | bromofenoxim, | (CAS 13181-17-4) |
| (B5.9) | butralin, | (CAS 33629-47-9) |
| (B5.10) | chloridazon/pyrazon, | (CAS 1698-60-8) |
| (B5.ll) | chlorthal, | (CAS 2136-79-0), (CAS 1861-32-1), (CAS 88754-7) |
| (B5.12) | cinîdon-ethyl, | (CAS 142891-20-1) |
| (B5.13) | cinmethyliii, | (CAS 87818-31-3) |
| (B5.14) | clomazone, | (CAS 81777-89-1) |
| (B5.15) | cyclopyrimorate, | (CAS 499231-24-2) |
| (B5.16) | dinîtramine. | (CAS 29091-05-2) |
| (B5.17) | diquat. | (CAS 2764-72-9), (CAS 85-00-7), (CAS 4032- 26-2) |
| (B5.18) | dithiopyr. | (CAS 97886-45-8) |
| (B5.19) | acetic acid, | (CAS 64-19-7) |
| (B5.2Ü) | ethalfluralin, | (CAS 55283-68-6) |
| (B5.21) | ethofumesate, | (CAS 26225-79-6) |
| (B5.22) | flamprop. | (CAS 58667-63-3, (CAS 90134-59-1), (CAS 63782-90-1), (CAS 63729-98-6) |
| (B5.23) | florpyrauxifen, | (CAS 943832-81-3), (CAS 1390661-72-9) |
| (B5.24) | flufenpyr. | (CAS 188490-07-5), (CAS 188489-07-8) |
| (B5.25) | flumiclorac, | (CAS 87547-04-4), (CAS 87546-18-7) |
| (B5.26) | fiumioxazin, | (CAS 103361-09-7) |
| (B5.27) | flurîdone, | (CAS 59756-60-4) |
| (B5.28) | flurochloridone, | (CAS 61213-25-0) |
| (B5.29) | flurtamone. | (CAS 96525-23-4) |
| (B5.30) | fluthiacet-methyl, | (CAS 149253-65-6) |
| (B5.31) | halauxifen. | (CAS 943832-60-8), (CAS 943831-98-9) |
| (B5.32) | indanofan. | (CAS 13320-30-1) |
| (B5.33) | norflurazon, | (CAS 27314-13-2) |
| (B5.34) | oleic acid, | (CAS 112-80-1) |
| (B5.35) | oryzalin. | (CAS 19044-88-3) |
| (B5.36) | oxaziclomefone, | (CAS 153197-14-9) |
| (B5.37) | paraquat, | (CAS 4685-14-7), (CAS 1910-42-5), (CAS 2074-50-2) |
| (B5.38) | pelargonic acid. | (CAS 112-05-0) |
| (B5.39) | pendimethalin. | (CAS 40487-42-1) |
| (B5.40) | pentoxazone, | (CAS 110956-75-7) |
| (B5.41) | pyridafol, | (CAS 40020-01-7) |
| (B5.42) | pyridate, | (CAS 55512-33-9) |
| (B5.43) | tetflupyrolimet. | (CAS 2053901-33-8) |
| (B5.44) | thiazopyr, | (CAS 117718-60-2) |
| (B5.45) | triafamone, | (CAS 874195-61-6) |
| (B5.46) | trifluralin, | (CAS 1582-09-8) |
| • | (B5.47) | 4-amino-3-chloro-5- fluoro-6-(7-fluoro-lH- | |
| i ndol -6-y l)pyridi ne-2- | |||
| carboxylic acid. | |||
| (B5.48) | cyclopyrimorate, | (CAS 499231-24-2) | |
| (B5.49) | diquat, | (CAS 2764-72-9, CAS 85-00-7, CAS4032-26-2) | |
| (B5.50) | oxaziclomefone, | (CAS 153197-14-9) | |
| (B5.51) | pentanochlor. | (CAS 2307-68-8) | |
| (B5.52) | tebutam, | (CAS 35256-85-0) | |
| (B5.53) | thidiazimin; | (CAS 123249-43-4) | |
| (B6) | represents active herbicidal ingrédients from the group of the (het)arylcarboxylic acids selected | ||
| from | |||
| (B6.1) | cliloramben, | (CAS 133-90-4), (CAS 1076-46-6), (CAS 53404-163), (CAS 7286-84-2), (CAS 25182-03-0), (1954-8 ΙΟ) | |
| (B6.2) | clopyralid, | (CAS 1702-17-6), (CAS 1532-24-7), (CAS 5775485-5), (CAS 58509-83-4), (CAS 73455-09-1) | |
| (B6.3) | dicamba, | (CAS 1918-00-9), (CAS 1286239-22-2), (CAS 104040-79-1), (CAS 2300-66-5), (CAS 25059-78-3), (CAS 55871-02-8), (CAS 6597-78-0), (CAS 5340428-7), (CAS 10007-85-9), (CAS 1982-69-0), (5340429-8), (CAS 56141-00-5) | |
| (B6.4) | fluroxypyr, | (CAS 69377-81-7), (CAS -27-8), (CAS 81406-37-3) | |
| (B6.5) | picloram, | (CAS 1918-02-1), (CAS 55870-98-9), (CAS 3637499-9), (CAS 26952-20-5), (CAS 14143-55-6), (CAS 55871-00-6), (CAS 2545-60-0), (CAS 35832-11-2), (CAS 6753-47-5), (CAS 82683-78-1) | |
| (B6.6) | quinclorac, | (CAS 84087-01-4), (CAS 84087-48-9), (CAS 8408733-2) | |
| (B6.7) | quinmerac, | (CAS 90717-03-6) | |
| (B6.8) | TBA, | (CAS 50-31-7), (CAS 3426-62-8), (CAS 71750-373), (CAS 4559-30-2), (CAS 2078-42-4) | |
| (B6.9) | trîchlopyr; | (CAS 55335-06-3), (CAS [64700-56-7), (CAS 1048373-85-8), (CAS 60825-27-6), (CAS 57213-691) |
(B7) represents active herbicida! ingrédients from the group of the organic phosphorus compounds selected from
| (B7.1) | aniiofos, | (CAS 64249-01-0) |
| (B7.2) | bialaphos. | (CAS 35597-43-4), (CAS 71048-99-2) |
| (B7.3) | butamifos, | (CAS 36335-67-8) |
| (B7.4) | glufosinate, | (CAS 51276-47-2), (CAS 35597-44-5), (CAS 77182-82-2), (CAS 35597-44-5), (CAS 70033-13-5) |
| (B7.5) | glyphosate, | (CAS 1071-83-6), (CAS 69254-40-6), (CAS 34494-04-7), (CAS 38641-94-0), (CAS 40465-66-5), (CAS 39600-42-5), (CAS 70393-85-0), (CAS 81591-81-3) |
| (B7.6) | piperophos, | (CAS 24151-93-7) |
| (B7.7) | sulfosate, | (CAS 1591-81-3) |
| (B7.8) | amiprofos; | (CAS 33857-23-7, CAS 36001-88-4) |
| (B8) represents active herbicidal ingrédients from the group of the phenyl ethers selected from | ||
| (B8.1) | 2,4-D, | (CAS 94-75-7), (CAS 2307-55-3), (CAS 192973-3), (CAS 1320-18-9), (CAS 1928-45-6), (CAS 94-80-4), (CAS 1048373-72-3), (CAS 20940-37-8), (CAS 2008-39-1), (CAS 574219-8), (CAS 2212-54-6), (CAS 533-23-3), (CAS 1928-43-4), (CAS 37102-63-9), (CAS 713-15-1), (CAS 25168-26-7), (CAS 94-11-1), (CAS 5742-17-6), (CAS 3766-27-6), (CAS |
| 1917-97-1), (CAS 1928-38-7), (CAS 1928-445), (CAS 1917-92-6), (CAS 1928-61-6), (CAS 2702-72-9), (CAS 15146-99-3), (CAS 2868518-9), (CAS 2646-78-8), (CAS 18584-79-7), (CAS 2569-01-9), (CAS 215655-76-8) | ||
| (B8.2) | 2,4-DB, | (CAS 94-82-6), (CAS 2758-42-1), (CAS 132015-6), (CAS 19480-40-1), (CAS 10433-59-7) |
| (B8.3) | 2,4-DP, | (CAS 120-36-5), (CAS 53404-31-2), (CAS 53404-32-3), (CAS 79270-78-3), (CAS 2863135-8), (CAS 57153-17-0), (CAS 5746-17-8), (CAS 39104-30-8) |
| (B8.4) | acifluorfen. | (CAS 50594-66-6), (CAS 50594-67-7), (CAS 62476-59-9) |
| (B8.5) | aclonifen, | (CAS 74070-46-5) |
| (B8.6) | bîfenox. | (CAS 42576-02-3) |
| (B8.7) | chlomethoxyfen, | (CAS 32861-85-1) |
| (B8.8) | clodinafop-propargyl, | (CAS 114420-56-3 ), (CAS 105512-06-9) |
| (B8.9) | clomeprop. | (CAS 84496-56-0) |
| (B8.10) | cyhalofop. | (CAS 122008-78-0), (CAS 122008-85-9) |
| (B8.ll) | diclofop, | (CAS 40843-25-2 ), (CAS 51338-27-3) |
| (B8.12) | ethoxyfen, | (CAS 188634-90-4), (CAS 131086-42-5) |
| (B8.13) | fenoxaprop, | (CAS 95617-09-7 ), (CAS 113158-40-0), (CAS 71283-80-2) |
| (B8.14) | fluazifop, | (CAS 69335-91-7), (CAS 83066-88-0), (CAS 79241-46-6) |
| (B8.15) | fluoroglycofen. | (CAS 77501-60-1), (CAS 77501-90-7) |
| (B8.16) | fomesafen, | (CAS 72178-02-0), (CAS 108731-70-0) |
| (B8.17) | halosafen. | (CAS 77227-69-1) |
| (B8.18) | haloxyfop, | (CAS 69806-34-4), (CAS 95977-29-0 ), (CAS 72619-32-0) |
| (B8.19) | lactofen, | (CAS 77501-63-4) |
| (B8.20) | MCPA, | (CAS 94-74-6), (CAS 19480-43-4), (CAS 1713-12-8), (CAS 2039-46-5), (CAS 2040519-0), (CAS 2698-38-6), (CAS 29450-45-1), (CAS 1713-11-7), (CAS 26544-20-7), (CAS 2698-40-0), (CAS 2436-73-9), (CAS 6365-624), (CAS 5221-16-9), (CAS 3653-48-3), (CAS 42459-68-7) |
| (B8.21) | MCPB, | (CAS 94-81-5), (CAS 10443-70-6), (CAS 57153-18-1), (CAS 6062-26-6) |
| (B8.22) | mecoprop, | (CAS 93-65-2), (CAS 32351-70-5), (CAS 1432-14-0), (CAS 71526-69-7), (CAS 2847303-2), (CAS 2786-19-8), (CAS 1929-86-8), (CAS 19095-88-6), (CAS 53404-61-8), (CAS 16484-77-8) |
| (B8.23) | metamifop, | (CAS 256412-89-2) |
| (B8.24) | oxyfluorfen. | (CAS 42874-03-3) |
| (B8.25) | propaquizafop, | (CAS 111479-05-1) |
| (B8.26) | quizalofop, | (CAS 76578-12-6), (CAS 76578-14-8), |
| (B8.27) | quizalofop-p, | (CAS 94051-08-8), (CAS 100646-51-3), (CAS 200509-41-7) |
| (B8.28) | benzfendizone; | (CAS 158755-95-4) |
(B9) represents active herbicidal ingrédients from the group of the pyrîmidines selected from
| (B9.1) | bispyrac-sodium, | |
| (B9.2) | bromacil, | (CAS 314-40-9), (CAS 53404-196), (CAS 69484-12-4) |
| (B9.3) | butafenacil, | (CAS 134605-64-4) |
| (B9.4) | lenacil, | (CAS 2164-08-1) |
| (B9.5) | pyribenzoxim, | (CAS 168088-61-7) |
| (B9.6) | pyriftalid, | (CAS 135186-78-6) |
| (B9.7) | pyriminobac, | (CAS 136191-56-5), (CAS 13619164-5) |
| (B9.8) | pyrimisulfan, | (CAS 221205-90-9) |
| (B9.9) | pyrithiobac-sodium, | (CAS 123342-93-8), (CAS 123343- 16-8) |
| (B9.10) | saflufenacil, | (CAS 372137-35-4) |
| (B9.ll) | terbacil, | (CAS 5902-51-2) |
| (B9.12) | tiafenacil, | (CAS 1220411-29-9) |
| (B9.13) (B9.14) | trifludimoxazin, ethyl [3-[2-chloro-4-fluoro-5-(l- | (CAS 1258836-72-4) |
methy 1-6-trifluorom ethyl-2,4dioxo-1,2,3,4tetrahydropyrimidin-3yl)phenoxy]-2pyridyloxy]acetate;
(B 10) represents active herbicidal ingrédients from the group of the (thio)ureas selected from
| (B10.1) | chlorobromuron, | |
| (B10.2) | chlorotoluron, | (CAS 15545-48-9) |
| (B10.3) | daimuron, | (CAS 42609-52-9) |
| (B10.4) | dimefuron, | (CAS 34205-21-5) |
| (B10.5) | dîuron, | (CAS 330-54-1) |
| (B10.6) | diflufenzopyr, | (CAS 1957168-02-3) |
(B10.7) fluometuron, (CAS 2164-17-2)
| (B10.8) | isoproturon, | (CAS 34123-59-6) |
| (B10.9) | linuron, | (CAS 330-55-2) |
| (B 10.10) | methabenzthiazuron, | (CAS 18691-97-9) |
| (B10.il) | metobromuron, | (CAS 3060-89-7) |
| (B10.12) | metoxuron. | (CAS 19937-59-8) |
| (B10.13) | monolinuron, | (CAS 1746-81-2) |
| (B10.14) | neburon, | (CAS 555-37-3) |
| (B10.15) | siduron, | (CAS 1982-49-6) |
| (B10.16) | tebuthiuron, | (CAS 34014-18-1) |
| (B10.17) | fenuron. | (CAS 101-42-8) |
| (B10.18) | chloroxuron. | (CAS 1982-47-4) |
| (B10.19) | diflufenzopyr, | (CAS 1957168-02-3, |
| CAS 109293-98-3) | ||
| (B 10.20) | ethidimuron; | (CAS 30043-49-3) |
(BU) represents active herbicidal ingrédients from the group of the triazines selected from
| (B11.1) | ametryne. | |
| (BU.2) | atrazine. | (CAS 1912-24-9) |
| (Bll.3) | cy nazi ne, | (CAS 21725-46-2) |
| (B 11.4) | dimethametryn, | (CAS 22936-75-0) |
| (BU.5) | hexazinone, | (CAS 51235-04-2) |
| (B 11.6) | indaziflam. | (CAS 950782-86-2) |
| (B 11.7) | metamitron. | (CAS 41394-05-2) |
| (B 11.8) | metribuzin, | (CAS 21087-64-9) |
| (BU .9) | prometon, | (CAS 1610-18-0) |
| (Bll. 10) | pro met ry ne, | (CAS 7287-19-6) |
| (Bll.11) | propazine, | (CAS 139-40-2) |
| (Bll.12) | simazine, | (CAS 122-34-9) |
| (Bll. 13) | simetryne. | (CAS 1014-70-6) |
| (BU.14) | terbumeton, | (CAS 33693-04-8) |
| (Bll.15) | terbuthylazine, | (CAS 5915-41-3) |
| (Bll.16) | terbutryne, | (CAS 886-50-0) |
| (Bll.17) | triaziflam, | (CAS 131475-57-5) |
| (Bll. 18) | trietazine, | (CAS 1912-26-1) |
| (Bll. 19) | desmetryne | (CAS 1014-69-3). |
The common name of the herbicides listed above is supplemented by the CAS RN (Chemical Abstracts
Service Registry Number) (CAS for short) between parenthèses. The CAS RN is a widely used reference number that enables unambiguous assigninent of the substances in question since the CAS RN distinguîshes inter alia between isomers, including stereoisomers, and salts and esters. For active ingrédients that exist in various forms, the name of the neutral compound is given in each case in the above list. The CAS given between parenthèses is directed to these and to ail further known forms of the active ingrédient. Only the neutral compound is ever mentîoned hereinafter, and hence encompasses ail existing forms as iisted, unless a spécifie form of the active ingrédient is relevant in a particular context, for example in table examples below for biological efficacy.
The compositions of the invention may contain further components, for example other active ingrédients to counter harmful organisms such as harmful plants, plant-damaging animais or plant-damaging fungi, especially active ingrédients from the group of the herbicides, fongicides, insecticides, acaricides, nematicides and miticides, and related substances, or else other kinds of active ingrédients for crop protection (e.g. résistance inductors), plant growth regulators, and/or additions and/or formulation auxiliaries that are customary in crop protection. The components may be formulated together here (readyto-use formulation) and employed as such, or they may be formulated separately and employed together, for example in a tankmix or in sequential application.
The individual active herbicidal ingrédients of the general formula (I) présent as component (A) are also referred to hereinafter as compounds (A), active ingrédients (A), components (A) or herbicides (A). Correspondingly, the individual active herbicidal ingrédients présent as component (B) are also referred to hereinafter as compounds (B), active ingrédients (B), components (B) or herbicides (B).
An advantageous property of the inventive combination of herbicides (A) and (B) is found to be that active ingrédients (A) and (B) are compatible with one another, meaning that they can be employed together without occurrence of significant Chemical incompatibility between the active ingrédients (A) and/or (B) that leads to destruction of one or more active ingrédients. This avoids any réduction in the active ingrédient content in formulations or spray liquors. The favourable compatibility also extends to the biological properties of the active ingrédients on combined use. For instance, antagoniste effects are generally not observed in the case of control of harmful plants with the active ingrédient combinations of the invention. The active ingrédients (A) and (B) are thus particularly suitable for employment together with or in addition to further active ingrédients for crop protection or agrochemicals. The combined application enabled permits the utilization of advantageous effects, for example the broadening of the spectrum of harmful plants to be controlled on application, or the réduction of the application rate of the individual herbicides (A) or (B) compared to the respective application rate of the herbicide in question in the case of individual application. It is thus possible to influence the dégradation characteristics of the active ingrédients and to achieve more favourable conditions for the subséquent growing of crop plants.
) A further advantage is considered to be that the development of résistances of the harmful plants to the active ingrédients can often be significantly reduced or avoided through the combination of active ingrédients having different mechanisms of action.
More particularly, superadditive (= synergistic) effects surprisingly occur in the case of combined use of 5 active ingrédients (A) and (B) for a greater number of economically important harmful plants. The activity in the combination is higher here than the expected sum of the activîties of the individual herbicides used. The synergistic effects allow the application rate to be reduced further, a broader spectrum of broadleaved weeds and weed grasses to be controlled, a more rapid onset of the herbicidal action, longer persislence, better control of the harmful plants with only one or a few applications, and extension of the application 10 period possible. To some extent, the use of the products also reduces the amount of harmful ingrédients, such as nitrogen or oleic acid, and their introduction into the soil.
Said properties and advantages are désirable in practical weed control in order to keep agricultural crops ciear of unwanted competing plants and hence to ensure and/or increase the yields in terms of quabty and quanti ty. The technical standard is clearly surpassed by the novel combinations with regard to the 15 properties described.
The synergistic effects are observed in the case of joint déployaient of active ingrédients (A) and (B), but can also frequently occur in the case of offset application (splitting). It is also possible to apply the herbicides (A) or (B) or the herbicidal composition (A) and (B) in multiple portions (sequential application). For example, one or more pre-emergence applications may be foliowed by a post-emergence 20 application, or an early post-emergence application may be followed by a moderately late or late postemergence application. Preference is given to the simultaneous or immediately successive application of the active ingrédients of the respective combination, if appropriate in several portions. But application of the individual active ingrédients of a combination at different times is also possible, and may be advantageous in the individual case. It is also possible to integrate other crop protection products into the 25 system for application, for example the other active ingrédients mentioned (other herbicides, fungicides, insecticides, acaricides etc.) and/or varions auxiliarîes, adjuvants and/or applications of fertilizer.
Application by the pre-emergence method or by the post-emergence method, according to the context in which the terms are used, is respectively understood to mean the application of the active ingrédients before and after the visible appearance of the harmful plants above the ground, or the use of the active 30 ingrédients against the harmful plants before emergence of the crop plants and after emergence of the crop plants.
In the formula (I) for compounds of the active herbicidal ingrédients (A) and ail the formuiae that follow, the following définitions are applicable:
Alkyl dénotés saturated straight-chain or branched hydrocarbyl radicals having the number of carbon atoms specified in each case, e.g. Ci-C6-alkyl such as methyl, ethyl, propyl, l-methylethyl, butyl, 1methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, bexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2methyipentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyi, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2trimethylpropyi, 1,2,2-trimethylpropyl, 1-elhyl-l-methylpropyl and l-ethyl-2-methylpropyl.
Halogen-substituted alkyl dénotés straight-chain or branched alkyl groups where some or ail of the hydrogen atoms in these groups may be replaced by halogen atoms, e.g. CrC2-haloalkyl such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl and 1,1,1trifluoroprop-2-yl.
Alkenyl dénotés unsaturated straight-chain or branched hydrocarbyl radicals having the number of carbon atoms stated in each case and one double bond in any position, for example Cz-Cô-alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2methyl-1-propenyl, l-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4pentenyl, 1-methyl-l-butenyl, 2-methyl-l-butenyl, 3-methyl-l-butenyl, l-methyl-2-butenyl, 2-methyl-2butenyl, 3-methyl-2-butenyl, l-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl2-propenyl, 1,2-dimethyl-1-propenyl, l,2-dimethyl-2-propenyl, 1-ethyl-l-propenyl, l-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl- 1-pentenyl, 3methyl-l-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2pentenyl, 4-methy]-2-pentenyl, l-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4methyl-3-pentenyl, l-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4pentenyl, l,l-dimethyl-2-butenyl, l,l-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, l,2-dimethyl-2butenyl, l,2-dîmethyl-3-butenyl, 1,3-dimethyl- 1-butenyl, l,3-dimethyl-2-butenyl, l,3-dimethyl-3butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3butenyl, 3,3-dimethyl-l-butenyl, 3,3-dimethyl-2-butenyi, 1-ethyl-l-bulenyl, l-ethyl-2-butenyl, l-ethyl-3butenyl, 2-ethyl- 1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-lmethyl-2-propenyl, l-ethyl-2-methyl-l-propenyl and 1-ethyl-2-methyl-2-propenyl.
Alkynyl dénotés straight-chain or branched hydrocarbyl radicals having the number of carbon atoms specified in each case and one triple bond in any position, e.g. C2-Cf,-alkynyl sucb as ethynyl, 1-propynyl, 2-propynyl (or propargyl), 1-butynyl, 2-butynyl, 3-butynyl, l-methyi-2-propynyl, 1-pentynyl, 2-pentynyl, b 3-pentynyl, 4-pentynyl, 3-methyl-l-bulynyl, l-methyl-2-butynyl, l-methyl-3-butynyl, 2-methyl-3butynyl, l,l-dîinethyl-2-propynyl, l-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5hexynyl, 3-methyl-l-pentynyl, 4-methyl-l-pentynyl, l-methyl-2-pentynyl, 4-methyl-2-pentynyl, 1methyl-3-pentynyl, 2-methyl-3-pentynyl, l-methyl-4-pentynyl, 2-methyJ-4-pentynyl, 3-methyl-45 pentynyl, l,l-dimethyl-2-butynyl, l,l-dimethyl-3-butynyl, l,2-dimethyl-3-butynyl, 2,2-dimethyl-3butynyl, 3,3-dimethyl-l-butynyl, l-ethyl-2-butynyl, l-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-lmethyl-2-propynyl.
Cycloalkyl dénotés a carbocyclic saturated ring System having preferably 3-8 ring carbon atoms, for 10 example cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl. In the case of optionally substituted cycloalkyl, cyclic Systems with substituents are included, also including substituents with a double bond on the cycloalkyl radical, for example an alkylidene group such as methylidene.
In the case of optionally substituted cycloalkyl, polycyclic aliphatic Systems are also included, for example bicyclo[1.1.0]butan-l-yl, bicyclo[1.1.0]butan-2-yl, bicyclo[2.1.0]pentan-l-yl, bicyclo[2.1.0]pentan-2-yl, 15 bicyclo[2.1.0]pentan-5-yl, bicyclo[2.2.1]hept-2-yl (norbornyl), adamantan-l-yl and adamantan-2-yJ.
In the case of substituted cycloalkyl, spirocyclic aliphatic Systems are also included, for example spiro[2.2]pent-l-yl, spiro[2.3]hex-l-yl, spiro[2.3]hex-4-yl, 3-spiro[2.3]hex-5-yl.
Cycloalkenyl dénotés a carbocyclic, nonaromatic, partially unsaturated ring system having preferably 48 carbon atoms, e.g. 1-cyclobutenyl, 2-cyclobutenyI, 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, 20 or 1-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl, 1,3-cyclohexadîenyl or 1,4-cyclohexadienyl, also including substituents with a double bond on the cycloalkenyl radical, for example an alkylidene group such as methylidene. In the case of optionally substituted cycloalkenyl, the élucidations for substituted cycloalkyl apply correspondingly.
Alkoxy dénotés saturated straight-chain or branched alkoxy radicals having the number of carbon atoms 25 specified in each case, for example Ci-C6-alkoxy such as methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1-dimethylethoxy, pentoxy, 1-methyl butoxy, 2methylbutoxy, 3-methylbutoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1dimethylbutoxy, 1,2-dimethyibutoxy, 1,3-dimethylbutoxy, 2,2-dimethyIbutoxy, 2,3-dimethylbutoxy, 3,330 dimethyibutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethyIpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl1-methylpropoxy and 1-ethy 1-2-methylpropoxy. Halogen-substituted alkoxy dénotés straight-chain or branched alkoxy radicals having the number of carboii atoms specified in each case, where some or ail of the hydrogen atoms in these groups may be replaced by halogen atoms as specified above, e.g. C1-C2haloalkoxy such as chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluoro methoxy, di fluoro methoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 1-chloroethoxy, 1-bromoethoxy, 1-fluoroethoxy, 2-fIuoroethoxy, 2,2difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chIoro-l,2-difiuoroethoxy, 2,2dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy and l,l,l-trifluoroprop-2-oxy.
The term aryl dénotés an optionally substituted mono-, bî- or polycyclic aromatic System having preferably 6 to 14, especially 6 to 10, ring carbon atoms, for example phenyl, naphthyl, anthryl, phenanthrenyi and the like, preferably phenyl.
The term optionally substituted aryl also embraces polycyclic Systems, such as tetrahydronaphthyl, 10 indenyl, indanyl, fluorenyl, bîphenylyl, where the bonding site is on the aromatic system. In systematic terms, aryl îs generally also encompassed by the term optionally substituted phenyl.
The aryïs listed above are preferably independently mono- to pentasubstituted, for exampie, by hydrogen, halogen, alkyl, haloalkyl, hydroxyl, alkoxy, cycloalkoxy, aryloxy, alkoxyalkyl, alkoxyalkoxy, cycloalkyl, halocycloalkyl, aryl, arylalkyl, heteroaryl, heterocyclyl, alkenyl, alkylcarbonyi, cycloalkylcarbotiyl, 15 arylcarbonyl, heteroarylcarbonyl, aikoxycarbonyl, hydroxycarbonyl, cycloalkoxycarbonyl, cycloalkylaikoxycarbonyl, alkoxycarbonylalkyl, arylalkoxycarbonyl, arylalkoxycarbonyl alkyl, alkynyl, alkynylalkyl, alkylalkynyl, trisalkylsilylalkynyl, nitro, amino, cyano, haloalkoxy, haloalkylthio, alkylthio, hydrothio, hydroxyalkyl, heteroarylalkoxy, arylalkoxy, heterocyclylalkoxy, heterocyclylalkylthîo, heterocyclyloxy, heterocyclylthio, heteroaryloxy, bisalkylamino, alkylamino, cycloalkylamino, 20 hydroxy carbonylalkylamino, alkoxycarbonylalkylamino, arylalkoxycarbonylalkylamino, alkoxycarbonylalkyl(alkyl)amino, aminocarbonyl, alkylaminocarbonyl, bisalkylaminocarbonyl, cycloalkylaminocarbonyl, hydroxycarbonylalkylaminocarbonyl, alkoxycarbonylalkylaminocarbonyl, arylalkoxycarbonylalkylaminocarbonyl.
A heterocyclic radical (heterocyclyl) contains at least one heterocyclic ring (=carbocyclic ring in which at 25 least one carbon atom has been replaced by a heteroatom, preferably by a heteroatom from the group of
N, O, S, P) which is saturated, unsaturated, partially saturated or heteroaromatic and may be unsubstituted or substituted, in which case the bonding site is localized on a ring atom. If the heterocyclyl radical or the heterocyclic ring is optionally substituted, it may be fused to other carbocyclic or heterocyclic rings. In the case of optionally substituted heterocyclyl, polycyclic Systems are also included, for example 830 azabicyclo[3.2.1]octanyl, 8-azabicyclo[2.2.2]octany] or l-azabicyclo[2.2.1]heptyl. In the case of optionally substituted heterocyclyl, spirocyclic Systems are also included, for example l-oxa-5azaspiro[2.3]hexyl. Unless defined differently, the heterocyclic ring preferably contains 3 to 9 ring atoms, especially 3 to 6 ring atoms, and one or more, preferably 1 to 4, especially 1, 2 or 3, heteroatoms in the heterocyclic ring, preferably from the group of N, O and S, but no two oxygen atoms should be directly
A adjacent, for example with one heteroatom from the group of N, O and S: 1- or 2- or 3-pyrrolidinyl, 3,4dihydro-2H-pyrrol-2- or 3-yl, 2,3-dihydro-lH-pyrrol-l- or 2- or 3- or 4- or 5-yl; 2,5-dihydro-lH-pyrroi-
1- or 2- or 3-yl, 1- or 2- or 3- or 4-piperidinyl; 2,3,4,5-tetrahydropyridin-2- or 3- or 4- or 5-yl or 6-yl; 1,2,3,6-tetrahydropyridin-l- or 2- or 3- or 4- or 5- or 6-yl; 1,2,3,4-tetrahydropyridin-l- or 2- or 3- or 4- or 5 5- or 6-yl; 1,4-dihydropyridin-l- or 2- or 3- or 4-yl; 2,3-dihydropyridîn-2- or 3- or 4- or 5- or 6-yi; 2,5- dihydropyridin-2- or 3- or 4- or 5- or 6-yl, 1- or 2- or 3- or 4-azepanyl; 2,3,4,5-tetrahydro-lH-azepifi-lor 2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,7-tetrahydro-lH-azepin-l- or 2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,6,7-tetrahydro-lH-azepin-l- or 2- or 3- or 4-yl; 3,4,5,6-tetrahydro-2H-azepin-2- or 3- or 4- or 5- or 6or 7-yl; 4,5-dihydro-lH-azepin-l- or 2- or 3- or 4-yl; 2,5-dihydro-lH-azepin-l- or -2- or 3- or 4- or 5- or 10 6- or 7-yl; 2,7-dihydro-lH-azepin-l- or -2- or 3- or 4-yl; 2,3-dihydro-lH-azepin-l- or -2- or 3- or 4- or 5or 6- or 7-yl; 3,4-dihydro-2H-azepin-2- or 3- or 4- or 5- or 6- or 7-yl; 3,6-dihydro-2H-azepin-2- or 3- or 4- or 5- or 6- or 7-yl; 5,6-dihydro-2H-azepîn-2- or 3- or 4- or 5- or 6- or 7-yl; 4,5-dihydro-3H-azepin-2or 3- or 4- or 5- or 6- or 7-yl; lH-azepiii-1- or -2- or 3- or 4- or 5- or 6- or 7-yl; 2H-azepin-2- or 3- or 4or 5- or 6- or 7-yl; 3H-azepio-2- or 3- or 4- or 5- or 6- or 7-yi; 4H-azepîn-2- or 3- or 4- or 5- or 6- or 7-yl, 15 2- or 3-oxolanyl (= 2- or 3-tetrahydrofuranyl); 2,3-dihydrofuran-2- or 3- or 4- or 5-yl; 2,5-dihydrofuran-
2- or 3-yl, 2- or 3- or 4-oxanyl (= 2- or 3- or 4-tetrahydropyranyl); 3,4-dihydro-2H-pyran-2- or 3- or 4- or 5- or 6-yl; 3,6-dihydro-2H-pyran-2- or 3- or 4- or 5- or 6-yl; 2H-pyran-2- or 3- or 4- or 5- or 6-yl; 4Hpyran-2- or 3- or 4-yl, 2- or 3- or 4-oxepanyl; 2,3,4,5-tetrahydrooxepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,7-tetrahydrooxepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,6,7-tetrahydrooxepin-2- or 3- or 4-yl; 2,320 dihydrooxepin-2- or 3- or 4- or 5- or 6- or 7-yl; 4,5-dihydrooxepin-2- or 3- or 4-yl; 2,5-dihydrooxepin-2or 3- or 4- or 5- or 6- or 7-yl; oxepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2- or 3-tetrahydrothiophenyl; 2,3dihydrothiophen-2- or 3- or 4- or 5-yl; 2,5-dihydrothiophen-2- or 3-yl; tetrahydro-2H-thiopyran-2- or 3or 4-yl; 3,4-dihydro-2H-thiopyran-2- or 3- or 4- or 5- or 6-yl; 3,6-dihydro-2H-thiopyran-2- or 3- or 4- or 5- or 6-yl; 2H-thiopyran-2- or 3- or 4- or 5- or 6-yl; 4H-thiopyran-2- or 3- or 4-yl. Preferred 3-membered 25 and 4-membered heterocycles are, for example, 1- or 2-aziridinyl, oxiranyl, tiüiranyl, 1- or 2- or 3- azetidinyl, 2- or 3-oxetanyl, 2- or 3-thietanyl, l,3-dioxetan-2-yl. Further examples of “heterocyclyl14 are a partly or fully hydrogenated heterocyclic radical having two heteroatoms from the group of N, O and S, for example 1- or 2- or 3- or 4-pyrazolidinyl; 4,5-dihydro-3H-pyrazol-3- or 4- or 5-yl; 4,5-dihydro-lHpyrazol-1- or 3- or 4- or 5-yl; 2,3-dihydio-lH-pyrazol-l- or 2- or 3- or 4- or 5-yl; 1- or 2- or 3- or 430 imidazolidinyl; 2,3-dihydro-lH-imidazol-l- or 2- or 3- or 4-yl; 2,5-dihydro-lH-imidazol-l- or 2- or 4- or
5-yl; 4,5-dihydro-lH-imidazol-l- or 2- or 4- or 5-yl; hexahydropyridazîn-1- or 2- or 3- or 4-yl; 1,2,3,4tetrahydropyridazin-1- or 2- or 3- or 4- or 5- or 6-yl; 1,2,3,6-tetrahydropyridazin-l- or 2- or 3- or 4- or 5or 6-yl; 1,4,5,6-tetrahydropyridazin-l- or 3- or 4- or 5- or 6-yl; 3,4,5,6-ietrahydropyridazin-3- or 4- or 5yl; 4,5-dihydropyridazin-3- or 4-yl; 3,4-dihydropyridazin-3- or 4- or 5- or 6-yl; 3,6-dihydropyridazin-335 or 4-yl; 1,6-dihydropyridazin-l- or 3- or 4- or 5- or 6-yl; hexahydropyrîmidin-l- or 2- or 3- or 4-yl; 1,4,5,6tetrahydropyrimidin-1- or 2- or 4- or 5- or 6-yl; 1,2,5,6-tetrahydropyrimidin-l- or 2- or 4- or 5- or 6-yl; 1,2,3,4-tetrahydropyrimidin-l- or 2- or 3- or 4- or 5- or 6-yl; 1,6-dihydropyrimidin-l- or 2- or 4- or 5- or
Φ 6-yl; 1,2-dihydropyrimidin-l- or 2- or 4- or 5- or 6-yl; 2,5-dihydropyrimidin-2- or 4- or 5-yl; 4,5dihydropyrimidin-4- or 5- or 6-yl; 1,4-dihydropyrimidin-l- or 2- or 4- or 5- or 6-yl; 1- or 2- or 3piperazinyl; 1,2,3,6-tetrahydropyrazin-l- or 2- or 3- or 5- or 6-yl; 1,2,3,4-tetrahydropyrazin-l- or 2- or 3or 4- or 5- or 6-yl; 1,2-dihydropyrazin-l- or 2- or 3- or 5- or 6-yl; 1,4-dihydropyrazin-l- or 2- or 3-y 1 ; 2,35 dihydropyrazin-2- or 3- or 5- or 6-yl; 2,5-dihydropyrazin-2- or 3-yl; l,3-dioxolan-2- or 4- or 5-yl; 1,3dioxol-2- or 4-yl; l,3-dioxan-2- or 4- or 5-yl; 4H-ï,3-dioxin-2- or 4- or 5- or 6-yl; l,4-dioxan-2- or 3- or 5- or 6-yl; 2,3-dihydro-l,4-dÎoxin-2- or 3- or 5- or 6-yl; l,4-dioxin-2- or 3-yl; l,2-dithiolan-3- or 4-yl; 3Hl,2-ditliiol-3- or 4- or 5-yl; l,3-dithiolan-2- or 4-yl; l,3-dithiol-2- or 4-yl; l,2-dithian-3- or 4-yl; 3,4dihydro-l,2-dithiin-3- or 4- or 5- or 6-yl; 3,6-dihydro-l,2-dithiin-3- or 4-yl; l,2-dithiin-3- or 4-yl; 1,310 dithian-2- or 4- or 5-yl; 4H-l,3-dithiin-2- or 4- or 5- or 6-yl; îsoxazoliditi-2- or 3- or 4- or 5-yl; 2,3dihydroisoxazol-2- or 3- or 4- or 5-yl; 2,5-dihydroisoxazol-2- or 3- or 4- or 5-yl; 4,5-dihydroisoxazol-3or 4- or 5-yl; l,3-oxazolidin-2- or 3- or 4- or 5-yl; 2,3-dihydro-l,3-oxazol-2- or 3- or 4- or 5-yl; 2,5dihydro-l,3-oxazol-2- or 4- or 5-yl; 4,5-dihydro-l,3-oxazol-2- or 4- or 5-yl; l,2-oxazinan-2- or 3- or 4- or 5- or 6-yl; 3,4-dihydro-2H-l,2-oxazin-2- or 3- or 4- or 5- or 6-yl; 3,6-dihydro-2H-l,2-oxazin-2- or 3- or 15 4- or 5- or 6-yl; 5,6-dihydro-2H-l,2-oxazin-2- or 3- or 4- or 5- or 6-yl; 5,6-dihydro-4H-l,2-oxazin-3- or
4- or 5- or 6-yl; 2H-l,2-oxazin-2- or 3- or 4- or 5- or 6-yl; 6H-l,2-oxazin-3- or 4- or 5- or 6-yl; 4H-1,2oxazin-3- or 4- or 5- or 6-yl; l,3-oxazinan-2- or 3- or 4- or 5- or 6-yl; 3,4-dihydro-2H-l,3-oxazin-2- or 3or 4- or 5- or 6-yl; 3,6-dihydro-2H-l,3-oxazin-2- or 3- or 4- or 5- or 6-yl; 5,6-dihydro-2H-l,3-oxazin-2or 4- or 5- or 6-yl; 5,6-dîhydro-4H-l,3-oxazin-2- or 4- or 5- or 6-yl; 2H-l,3-oxazin-2- or 4- or 5- or 6-yl;
6H-l,3-oxazin-2- or 4- or 5- or 6-yl; 4H-l,3-oxazin-2- or 4- or 5- or 6-yl; morpholin-2- or 3- or 4-yl; 3,4dihydro-2H-l,4-oxazin-2- or 3- or 4- or 5- or 6-yl; 3,6-dihydro-2H-l,4-oxazin-2- or 3- or 5- or 6-yl; 2Hl,4-oxazin-2- or 3- or 5- or 6-yl; 4H-l,4-oxazin-2- or 3-yl; l,2-oxazepan-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,5-tetrahydro-l,2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,7-tetrahydro-l,2-oxazepin-2- or 3or 4- or 5- or 6- or 7-yl; 2,3,6,7-tetrahydro-l,2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,5,6,725 tetrahydro-l,2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 4,5,6,7-tetrahydro-l,2-oxazepin-3- or 4- or 5- or 6- or 7-yl; 2,3-dihydro-l,2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,5-dihydro-l,2-oxazepin-2- or 3or 4- or 5- or 6- or 7-yl; 2,7-dîhydro-l,2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 4,5-dihydro-l,2oxazepin-3- or 4- or 5- or 6- or 7-yi; 4,7-dihydro-l,2-oxazepin-3- or 4- or 5- or 6- or 7-yl; 6,7-dihydrol,2-oxazepin-3- or 4- or 5- or 6- or 7-yl; l,2-oxazepin-3- or 4- or 5- or 6- or 7-yl; l,3-oxazepan-2- or 330 or 4- or 5- or 6- or 7-yl; 2,3,4,5-tetrahydro-l,3-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,7tetrahydro-l,3-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,6,7-tetrahydro-l,3-oxazepin-2- or 3- or 4- or
5- or 6- or 7-yl; 2,5,6,7-tetrahydro-l,3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 4,5,6,7-tetrahydro-l,3oxazepin-2- or 4- or 5- or 6- or 7-yl; 2,3-dihydro-l,3-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,5dihydro-l,3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 2,7-dihydro-l,3-oxazepin-2- or 4- or 5- or 6- or 7-yl;
4,5-dihydro-l,3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 4,7-dihydro-l,3-oxazepin-2- or 4- or 5- or 6- or 7yl; 6,7-dihydro-l,3-oxazepin-2- or 4- or 5- or 6- or 7-yl; l,3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 1,4oxazepan-2- or 3- or 5- or 6- or 7-yl; 2,3,4,5-tetrahydro-l,4-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl;
A 2,3,4,7-tetrahydro-1,4-oxazepîn-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,6,7-tetrahydro-l,4-oxazepin-2- or 3or 5- or 6- or 7-yi; 2,5,6,7-tetrahydro-l,4-oxazepin-2- or 3- or 5- or 6- or 7-yl; 4,5,6,7-tetrahydro-l,4oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3-dihydro-l,4-oxazepin-2- or 3- or 5- or 6- or 7-yl; 2,5dihydro-l,4-oxazepin-2- or 3- or 5- or 6- or 7-yl; 2,7-dihydro-l,4-oxazepin-2- or 3- or 5- or 6- or 7-yi;
4,5-dihydro-l,4-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 4,7-dihydro-l,4-oxazepin-2- or 3- or 4- or 5or 6- or 7-yl; 6,7-dihydro-l,4-oxazepin-2- or 3- or 5- or 6- or 7-yl; l,4-oxazepin-2- or 3- or 5- or 6- or 7yl; isothiazoiidin-2- or 3- or 4- or 5-yl; 2,3-dihydroisothiazol-2- or 3- or 4- or 5-yl; 2,5-dihydroisothiazol2- or 3- or 4- or 5-yl; 4,5-dihydroisothîazoi-3- or 4- or 5-yl; l,3-thiazolidin-2- or 3- or 4- or 5-yl; 2,3dihydro-l,3-lhîazol-2- or 3- or 4- or 5-yl; 2,5-dihydro-l,3-thiazol-2- or 4- or 5-yl; 4,5-dihydro-l,3-thiazol10 2- or 4- or 5-yl; l,3-thiazinan-2- or 3- or 4- or 5- or 6-yl; 3,4-dihydro-2H-l,3-thiazin-2- or 3- or 4- or 5or 6-yl; 3,6-dihydro-2H-l,3-thiazin-2- or 3- or 4- or 5- or 6-yl; 5,6-dihydro-2H-l,3-thiazin-2- or 4- or 5or 6-yl; 5,6-dihydro-4H-l,3-thiazin-2- or 4- or 5- or 6-yl; 2H-l,3-thiazin-2- or 4- or 5- or 6-yl; 6H-1,3lhiazin-2- or 4- or 5- or 6-yl; 4H-l,3-thiazin-2- or 4- or 5- or 6-yl. Further examples of heterocyclyl are a parti y or fully hydrogenated heterocyclic radical having 3 heteroatoms from the group of N, O and S, 15 for example l,4,2-dioxazolidin-2- or 3- or 5-yl; l,4,2-dioxazol-3- or 5-yl; l,4,2-dioxazinan-2- or -3- or 5or 6-yl; 5,6-dihydro-l,4,2-dioxazin-3- or 5- or 6-yl; l,4,2-dioxazin-3- or 5- or 6-yl; l,4,2-dioxazepan-2or 3- or 5- or 6- or 7-yl; 6,7-dihydro-5H-l,4,2-dioxazepin-3- or 5- or 6- or 7-yl; 2,3-dihydro-7H-l,4,2dioxazepin-2- or 3- or 5- or 6- or 7-yl; 2,3-dihydro-5H-l,4,2-dioxazepin-2- or 3- or 5- or 6- or 7-yl; 5Hl,4,2-dioxazepin-3- or 5- or 6- or 7-yl; 7H-l,4,2-dioxazepin-3- or 5- or 6- or 7-yl.
The heterocycles listed above are preferably independently mono- to hexasubstituted, for example, by hydrogen, halogen, alkyl, haloalkyl, hydroxyl, aikoxy, cycloalkoxy, aryloxy, alkoxyalkyl, aikoxyalkoxy, cycloalkyl, halocycloaikyl, aryl, arylalkyl, heteroaryl, heterocyclyl, alkenyl, alkylcarbonyl, cycioalkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, alkoxycarbonyl, hydroxycarbonyl, cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, alkoxycarbonylalkyl, arylalkoxycarbonyl, 25 arylalkoxycarbonylalkyl, alkynyl, alkynylaïkyl, alkylalkynyl, trisalkylsilylalkynyl, nitro, amino, cyano, baloalkoxy, haloalkylthio, alkylthio, hydrothio, hydroxyalkyl, oxo, heteroarylalkoxy, arylalkoxy, heterocyclylalkoxy, heterocyclylalkylthio, heterocyclyloxy, heterocyclylthio, heteroaryloxy, bîsalkylamino, alkylamino, cycloalkylamino, hydroxycarbonylalkylamino, alkoxycarbonylalkylamino, arylalkoxycarbonylalkylamino, alkoxycarbonylalkyl(aJkyl)amino, amînocarbonyl, alkylaminocarbonyl, bisalkylaminocarbonyl, cycloalkylaminocarbonyl, hydroxycarbonylalkylaminocarbonyl, alkoxycarbonylalkylaminocarbonyl, arylalkoxycarbonyialkylaminocarbonyl.
When a base structure is substituted by one or more radicals from a list of radicals (= group) or a generically defined group of radicals, this in each case includes simultaneous substitution by a plurality of identical and/or structurally different radicals.
In the case of a partially or fully saturated nitrogen heterocycle, this may be joined to the remainder of the h moiecule either via carbon or via the nitrogen.
Suitable substituents for a substituted heterocyclic radical are the substituents specified further down, and additionally also oxo and thioxo. The oxo group as a substituent on a ring carbon atom is then, for example, a carbonyl group in the heterocyclic ring. As a resuit, lactones and lactams are preferably also included.
The oxo group may also occur on the ring heteroatoms, which may exist în different oxidation States, for example in the case of N and S, and in that case form, for example, the divalent -N(0)-, -S(O)- (also SO for short) and S(O)2 (also SO2 for short) groups in the heterocyclic ring. In the case of -N(0)- and -S(O)groups, both enantiomers in each case are included.
According to the invention, the expression heteroaryl represents heteroaromatic compounds, i.e. fully 10 unsaturated aromatic heterocyclic compounds, preferably 5- to 7-membered rings having 1 to 4, preferably or 2, identical or different heteroatoms, preferably O, S or N. Inventive heteroaryls are, for example, lH-pyrrol-l-yi; lH-pyrroi-2-yl; lH-pyrrol-3-yl; furan-2-yl; furan-3-yl; thien-2-yl; thien-3-yl, 1Himidazol-l-yl; lH-imidazol-2-yl; lH-imidazol-4-yl; lH-imidazol-5-yl; IH-pyrazol-l-yl; lH-pyrazol-3yl; lH-pyrazol-4-yl; lH-pyrazol-5-yl, lH-l,2,3-triazobl-yl, lH-l,2,3-triazol-4-yl, lH-l,2,3-triazol-5-yi, 15 2H-l,2,3-triazol-2-yl, 2H-l,2,3-triazol-4-yl, lH-l,2,4-trîazol-l-yl, lH-l,2,4-triazol-3-yl, 4H-1,2,4triazol-4-yl, l,2,4-oxadiazol-3-yl, l,2,4-oxadîazoi-5-yl, l,3,4-oxadiazol-2-yl, l,2,3-oxadiazoi-4-yl, 1,2,3oxadiazol-5-yl, l,2,5-oxadiazol-3-yl, azepinyl, pyridîn-2-yl, pyridin-3-yl, pyridin-4-yl, pyrazin-2-yl, pyrazin-3-yl, pyrimidin-2-yl, pyrimidin-4-yl,pyrimidin-5-yl, pyridazîn-3-yl, pyridazin-4-yl, 1,3,5-triazin2-yl, l,2,4-triazin-3-yl, l,2,4-triazin-5-yl, l,2,4-triazin-6-yl, l,2,3-triazin-4-yl, l,2,3-triazîn-5-yl, 1,2,4-, 20 1,3,2-, 1,3,6- and 1,2,6-oxazinyI, isoxazol-3-yl, isoxazoi-4-yl, isoxazol-5-yI, l,3-oxazol-2-yl, 1,3-oxazol-
4-yl, l,3-oxazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, l,3-thiazol-2-yl, l,3-thiazol-4-yl, l,3-thiazol-5-yl, oxepinyl, thiepinyl, 1,2,4-triazolonyl and 1,2,4-diazepînyl, 2H-l,2,3,4-tetrazol-5-yl, 1Hl,2,3,4-tetrazol-5-yl, l,2,3,4-oxatriazol-5-yl, l,2,3,4-thiatriazol-5-yl, l,2,3,5-oxatriazol-4-yl, 1,2,3,5thiatriazol-4-yl. The heteroaryl groups of the invention may also be substituted by one or more identical 25 or different radicals. If two adjacent carbon atoms are part of a further aromatic ring, the Systems are fused heteroaromatic Systems, such as benzofused or polyannelated heteroaromatics.
Preferred examples are quinolines (e.g. quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinoIin-6-yl, quinolm-7-yl, quinolin-8-yl); isoquinolines (e.g. isoquifiolin-l-yl, isoquînolin-3-yl, isoquinolin-4-yl, isoquinolin-5-yl, isoquinolin-6-yl, isoquinolin-7-yl, isoquinolin-8-yl); quinoxaline; 30 quinazoline; cinnoline; 1,5-naphthyridine; 1,6-naphthyridine; 1,7-naphthyridine; 1,8-naphthyridine; 2,6naphthyridine; 2,7-naphthyridine; phthalazine; pyridopyrazines; pyridopyrimidines; pyridopyridazines; pteridines; pyrimidopyrimidines. Examples of heteroaryl are also 5- or 6-membered benzofused rings from the group of IH-indol-l-yl, lH-indol-2-yl, lH-indol-3-yl, ÏH-indol-4-yl, lH-indoI-5-yl, IH-indot6-yl, lH-indol-7-yl, l-benzofuran-2-yl, l-benzofuran-3-yl, l-benzofuran-4-yl, l-benzofuran-5-yl, 135 benzofuran-6-yI, l-benzofuran-7-yl, l-benzothiophen-2-yI, l-benzothiophen-3-yl, l-benzothiophen-4-yl, l-benzothiophen-5-yl, l-benzothiophen-6-yl, l-benzothiophen-7-yl, IH-indazol-l-yl, lH-indazol-3-yl, lH-indazol-4-yl, lH-rndazol-5-yl, IH-mdazol-o-yl, lH-indazol-7-yl, 2H-indazol-2-yl, 2H-indazol-3-yl, 2H-indazol-4-yl, 2H-indazol-5-yl, 2H-Îndazof6-yl, 2H-indazol-7-yl, 2H-isoindol-2-yi, 2H-isoindol-l-yl, 2H-isoindol-3-y], 2H-isoindol-4-yl, 2H-isoindol-5-yl, 2H-isoindol-6-yl; 2H-isoindol-7-y], 1Hbenzimidazol-l-yl, lH-benzimidazol-2-yl, lH-benzimidazol-4-yl, lH-benzimîdazol-5-yl, 1Hbenzimidazol-6-yl, lH-benzimidazol-7-yl, l,3-benzoxazoi-2-yl, l,3-benzoxazol-4-yl, l,3-benzoxazol-5yl, l,3-benzoxazol-6-yI, l,3-benzoxazol-7-yi, l,3-benzothiazol-2-yl, l,3-benzothiazol-4-yl, 1,3benzothiazol-5-yl, l,3-benzothiazol-6-yl, l,3-benzothiazol-7-yl, l,2-benzisoxazol-3-yl, 1,2-benzisoxazol4-yI, l,2-benzisoxazol-5-yl, l,2-benzisoxazol-6-yl, l,2-benzisoxazol-7-yl, l,2-benzisothîazol-3-yl, 1,2benzisothîazol-4-yl, l,2-benzisothiazol-5-yl, l,2-benzisothiazol-6-yl, l,2-benzisothiazol-7-yl.
Independently of one another, the heteroaryls listed above are preferably mono- to tetrasubstituted, for example, by hydrogen, halogen, alkyl, haloalkyl, hydroxyl, alkoxy, cycloalkoxy, aryloxy, alkoxyalkyl, alkoxyalkoxy, cycloalkyl, halocycloalkyl, aryl, arylalkyl, heteroaryl, heterocyclyl, alkenyl, alkylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, alkoxy carbonyl, hydroxycarbonyl, cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, alkoxycarbonylalkyl, arylalkoxycarbonyl, arylalkoxycarbonylalkyl, alkynyl, alkynylalkyl, alkylalkynyl, trisalkylsilylalkynyl, nitro, amino, cyano, haloalkoxy, haloalkylthio, alkylthio, hydrothio, hydroxyaikyl, oxo, heteroarylalkoxy, arylalkoxy, heterocyclylalkoxy, heterocyclylalkylthio, heterocyclyioxy, heterocyclyl thio, heteroaryloxy, bisalkylamino, alkylamino, cycloalkylamino, hydroxycarbonylalkylamino, alkoxycarbonylalkylamino, arylalkoxycarbonylalkylamino, alkoxycarbonylalkyl(alkyi)amîno, aminocarbonyl, alkylaminocarbonyl, bisaikyl ami nocarbo ny 1, cy cloalky lami nocarbon y 1, hy droxy carbo ny lalky laminocarbony 1, alkoxycarbonylalkylaminocarbonyl, arylalkoxycarbonylalkylaminocarbonyl.
The term halogen means fluorine, chlorine, bromine or iodine. If the term is used for a radical, halogen means a fluorine, chlorine, bromine or iodine atom.
According to the nature of the substituents and the way in which they are joined, the compounds of the formula (I) may be présent as stereoisomers. If, for example, there are one or more asymmetrically substituted carbon atoms and/or sulfoxides, it is possible for enantiomers and diastereomers to occur. Stereoisomers can be obtained from the mixtures obtained in the préparation by customary séparation methods, for example by chromatographie séparation processes. It is likewise possible to selectively préparé stereoisomers by using stereoselectîve reactions with use of optîcally active starting materials and/or auxiliaries.
The invention also relates to ail stereoisomers and mixtures thereof which are encompassed by the formula (I) but not defined specifically. For the sake of simplicity, however, reference will always be made hereinafter to compounds of the formula (I), even though this means not only the pure compounds but also, if appropriate, mixtures with different proportions of isomeric compounds.
According to the nature of the substituents defined above, the compounds of the formula (I) hâve acidic properties and can form salts, and if appropriate also internai salts or adducts with inorganic or organic bases or with métal ions. If the compounds of the formula (I) bear hydroxyl, carboxyl or other groups which induce acidic properties, these compounds can be reacted with bases to give salts.Suitable bases are, for example, hydroxides, carbonates, hydrogencarbonates of the alkali metals and alkaline earth metals, especially those of sodium, potassium, magnésium and calcium, and also ammonia, primary, secondary and tertiary amines having (Ci-C4)-alkyl groups, mono-, di- and trialkanolamines of (C1-C4)alkanols, cholinc and chlorocholine, and organic amines, such as trialkylamines, morpholine, pipcridine or pyridine. These salts arc compounds in which the acidic hydrogen is replaced by an agriculturally suitable cation, for example métal salts, especially alkali meta! salts or alkaline earth meta! salts, especially sodium and potassium salts, or else ammonium salts, salts with organic amines or quaternary ammonium salts, for example with cations of the formula [NRR'R'R']+ in which R to R' are each independentiy an organic radical, especially alkyl, aryl, aralkyl or alkylaryl. Also suitable are alkylsulfonium and alkylsulfoxonium salts, such as (C]-C4)-trialkylsulfonjum and (Ci-C4)-trialkylsulfoxonium salts.
The compounds of the formula (I) can form salts by addition of a suitable inorganic or organic acid, for example minerai acids, for example HCl, HBr, H2SO4, H3PO4 or HNO3, or organic acids, for example carboxylic acids such as formîc acid, acetic acid, propionic acid, oxalîc acid, lactic acid or salicylic acid or sulfonic acids, for example p-toluenesulfonic acid, onto a basic group, for example amino, alkylamino, dialkylamino, piperidino, morpholino or pyridino. In such a case, these salts comprise the conjugale base of the acid as the anion.
Suitable substituents présent in deprotonated form, for example sulfonic acids or carboxylic acids, may form internai salts with groups which for their part can be protonated, such as amino groups.
If a group is polysubstituted by radicals, this means that this group is substituted by one or more identical or different radicals from those mentioned.
In ail the formuiae specified hereinafter, the substituents and symbols hâve the same meaning as described in the general formula (I) of the herbicides (A), unless defined differently. Arrows in a Chemical formula dénoté the points at which it is joined to the rest of the molecuie.
There follows a description of preferred, more preferred and even more preferred meanings for each of the individual substituents of the herbicides (A) of the general formula (1), as shown above. The other substituents of the herbicides (A) of the general formula (I) which are not specified hereinafter hâve the définition given above.
In a Ist embodiment of the présent invention,
R1 and R2 are preferably each independently hydrogen, fluorine, chlorine or cyano, or are (Ci-C3)-alkyl or (Ci-C3)-alkoxy, each substituted by m radicals from the group consisting of fluorine, chlorine, bromîne and cyano.
More preferably, R1 and R2 are each independently hydrogen, fluorine, chlorine or cyano, or are methyl or methoxy, each substituted by m radicals from the group consisting of fluorine and chlorine.
Most preferably, R1 and R2 are each hydrogen.
in a 2nd embodiment of the présent invention,
R3 is preferably cyano, or (CrQj-aikyl, (Cj-CQ-cycloalkyl, (C2-C4)-alkenyl, (C^-CQ-aikynyl or (CiQj-alkoxy, each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, cyano, (Ci-C4)-alkoxy and hydroxy.
More preferably, R3 is (Ci-C3)-alkyl, (C3-C4)-cycloalkyl, (C2-C3)-aikenyl or (Ci-C3)-alkoxy, each substituted by m radicals from the group consisting of fluorine, chlorine and (Ci-C3)-aIkoxy.
In a 3rd embodiment of the présent invention,
R4 is preferably hydrogen, or (Ci-Csj-alkyl, (C3-Cs)-cycloalkyl, (Cj-CQ-cycloalkyl-fCi-CQ-alkyl, (C2Cû)-alkenyl, (Cs-CftJ-cycloalkenyl or (Cz-Qj-alkynyl, each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, cyano, (Cj-CQ-alkoxy, hydroxy and aryl.
Preferably, R4 is hydrogen, or (Ci-C3)~alkyl or (Cï-CQ-alkenyl, each substituted by m radicals from the group consisting of fluorine, chlorine and (Ci-Czj-alkoxy.
In a 4th embodiment of the présent invention, Y is oxygen.
In a 5th embodiment of the présent invention, W is oxygen.
In a 6th embodiment of the présent invention,
Z is preferably aZ-1 to Z-22 group, where Z-l to Z-22 are defîned as follows:
Z-21
Z-22 where the arrow in each case represents a bond to the group C=W of the formula (I).
More preferably, Z is a Z-l to Z-12 group, where Z-l to Z-12 are defined as follows:
where the arrow in each case represents a bond to the group C=W of the formula (I).
Most preferably, Z is Z-l, Z-4 or Z-6:
7.1 Z-4 Z-6 '
where the arrow in each case represents a bond to the group C=W of the formula (I).
In a 7th embodiment of the présent invention,
R1(1 is preferably fluorine, chlorine, cyano, CO2H, CO2CH3 or CO2CH2CH3, or (Ci-Caj-alkyl or (C1-C2)alkoxy, each substituted by m radicals from the group consisting of fluorine and chlorine.
In an 8th embodiment of the présent invention,
R11 is preferably hydrogen, or (Ci-C3)-alkyl or (Ci-Côj-cycloalkyl, each substituted by m radicals from the group consisting of fluorine and chlorine.
More preferably, R11 is hydrogen or (Ci-C^j-alkyL
M Most preferably, R11 is hydrogen.
In a 9th embodiment of the présent invention,
R12 is preferably hydrogen, cyano, OR7, S(O)n R5, SOzNR6R7, COR6, NR6R8, NR6COR8 or NR6SO3R8, or (Ci-CQ-alkyl, (Cs-Qj-cycloalkyl, (Cz-CyJ-alkenyl or (C^Cjj-alkynyl, each substituted by m radicals 5 from the group consisting of fluorine, chlorine, bromine, cyano, OR7, S(O)nR5, NR6RS and NR6COzR8.
More preferably, R12 îs OR7, S(O)nR5, SOîNR6R7, or (Ci-CQ-alkyl substituted in each case by m radicals from the group consisting of fluorine, chlorine, cyano, OR7 and S(O)nR5.
In a lOth embodiment of the présent invention,
R11 and R12 together with îhe nitrogen atom to which they are bonded preferably form a saturated or partly 10 or fully unsaturated five-, six- or seven-membered ring which is optionally mono- to hexasubstituted by radicals from the group consisting of halogen, cyano, nitro, (Ci-Cfi)-alkyl, halo-(Ci-C6)-aIkyl, oxo, OR7, S(O)n R5, CO2RK, COR6, NR6COR8 and NR6SO2RS and which, în addition to that nitrogen atom, contains r carbon atoms, o oxygen atoms, p sulfur atoms and q éléments from the group consisting of N R7 and NCOR7 as ring atoms.
More preferably, R11 and R12 together with the nitrogen atom to which they are bonded form a saturated or partly or fully unsaturated five-, six- or seven-membered ring which is optionally mono- to hexasubstituted by radicals from the group consisting of halogen, cyano, nitro, (Ci-C6)-alkyl, halo-(Cr Côj-alkyl, oxo, OR7, CO2R8 and NR6SO2Rs and which, in addition to that nitrogen atom, contains r carbon atoms, o oxygen atoms, p sulfur atoms and q éléments from the group consisting of NR7 and NCOR7 as 20 ring atoms.
Most preferably, R11 and R12 together with the nitrogen atom to which they are bonded form a saturated or partly or fully unsaturated five- or six-membered ring which is optionally mono- to trisubstituted by radicals from the group consisting of halogen, (Ci-C6)-alkyl, halo-(Ci~C6)-alkyl and oxo and which, in addition to that nitrogen atom, contains r carbon atoms, o oxygen atoms, p sulfur atoms and q éléments 25 from the group consisting of NR7 and NCOR7 as ring atoms.
In an 1 Ith embodiment of the présent invention,
X2, X4and X6 are preferably each îndependently hydrogen, fluorine, chlorine, bromine or cyano, or are methyl or methoxy, each substituted by m radicals from the group consisting of fluorine and chlorine.
More preferably, X2, X4 and X6 are îndependently hydrogen or fluorine.
Most preferably, X2, X4 and X6 are hydrogen.
ln a 12th embodiment of the présent invention,
X3 and X5 are preferably each independently hydrogen, fluorine, chlorine, bromine, hydroxy or cyano, or are (Cj-Cjj-alkyl, (Ci-Ci)-alkoxy, (Q-CQ-cycloalkyl, (C2-C3)-alkenyl or (C2-C3)-alkynyl, each substituted by m radicals from the group consisting of fluorine, chlorine and bromine.
More preferably, X3 and X’ are each independently hydrogen, fluorine, chlorine, cyano, CF3, CHF2 or methyl.
Most preferably, X3 and X5 are each independently hydrogen, fluorine, cyano or methyl.
At the very most preferably, X3 and X5 are each fluorine.
In a 13th embodiment of the présent invention,
R5 is preferably (Ci-CQ’alkyl or (Cé-CQ-cycloalkyl, each substituted by m radicals from the group consisting of fluorine and chlorine.
In a 14th embodiment of the présent invention,
R7 is preferably hydrogen, or (CrCQ-alkyl or (Cî-Côj-cycioalkyl, each substituted by m radicals from the group consisting of fluorine, chlorine and (Ci-Csj-alkoxy.
In a 15th embodiment of the présent invention,
R8 is preferably hydrogen, or (Ci-Côj-alkyi or (Ci-Cfj-cycloaikyl, each substituted by m radicals from the group consisting of fluorine, chlorine and (Ci-Cjj-alkoxy.
In a 16th embodiment of the présent invention, the index m is preferably 0,1, 2 or 3.
In the context of the présent invention, the individual preferred, more preferred and most preferred définitions of the substituents R1 to R8, R10 to R12, X2 to X6, W, Y and Z, and the indices k, m, n, o, p, q and r, may be combined with one another as desired.
This means that the présent invention encompasses compounds of the general formula (1) in which, for example, the substituent R1 has a preferred définition and the substituents R5 to R7 hâve the general définition or else the substituent R2 has a preferred définition, the substituent R3 has a more preferred or even more preferred définition and the remaining substituents hâve a general définition.
Six of these combinations of the définitions given above for the substituents R1 to R8, R10 to R12, X2 to Xû, W, Y and Z, and for the indices k, m, n, o, p, q and r are iliustrated hereinafter by way of example, and
B each of them is disclosed as a further embodiment:
In a 17th embodiment of the présent invention,
G is a group of the formula OR4;
R1 and R2 are each independently hydrogen, fluorine, chlorine or cyano, or are (CrQQ-alkyl or (Cj-C3)-alkoxy, each substituted by m radicals from the group consisting of fluorine, chlorine, bromine and cyano;
R3 is cyano, or (Ci-Qi)-alkyl, (Cj-C^-cycloalkyl, (C2-C3)-alkenyI, (C2-C?)-alkynyl or (Cj-Ca)-alkoxy, each 10 substituted by m radicals from the group consisting of fluorine, chlorine, bromine, cyano, (Cj-C?)alkoxy and hydroxy;
R4 is hydrogen, or (Ci-C6)-alkyl, (CvCfi/bcycloalkyl, (C3-Ct,)-cycloalkyl-(CrC6)-alkyl, (C2-C6)alkenyl, (C5-C6)-cycloalkenyl or (C2-Ce)-alkynyl, each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, cyano, (Ci-C4)-alkoxy, hydroxy and aryl;
Ύ is oxygen;
W is oxygen;
Z is a Z-l to Z-12 group, where Z-l to Z-12 are defined as follows:
where ihe arrow in each case represents a bond to the group C=W of the formula (I);
X2, X4 and X6 are each independently hydrogen, fluorine, chlorîne, bromine or cyano, or are methyl or methoxy, each substituted by m radicals from the group consisting of fluorine and chlorîne;
X3 and X’’ are each independently hydrogen, fluorine, cyano or methyl; and m is the index 0, 1, 2 or 3.
In an 18th embodiment of the present invention,
G is a group of the formula OR4;
R1 and R2 are each hydrogen;
R3 is (Ci-Cî)-alkyl, (Cj-C^-cycloalkyl, (C2-C3)-alkenyl or (Ci-C3)-alkoxy, each substituted by m radicals from the group consisting of fluorine, chlorîne and (C]-C2)-alkoxy;
R4 is hydrogen, or (Ci-C3)-alkyl or (C2-C*)-alkenyl, each substituted by m radicals from the group consisting of fluorine, chlorîne and (Cj-C2)-alkoxy;
Y is oxygen;
W is oxygen;
Z is a Z-l, Z-4 or Z-6 group:
2-i Z-4 Z-6 where the arrow in each case represents a bond to the group C=W of the formula (I);
X2, X4 and X6 are each independently hydrogen or fluorine;
X3 and X5 are each independently hydrogen, fluorine, cyano or methyl; and m is the index 0,1, 2 or 3.
hi a 19th embodiment of the présent invention,
G is a group of the formula OR4;
R1 and R2 are each hydrogen;
R3 is (Ci-C2)-alkyl, (Ca-C^-cycloalkyl, (C2-C2)-alkenyl or (Ci-C2)-alkoxy, each substituted by m radicals from the group consistîng of fluorine, chlorine and (Ci-C2)-alkoxy;
R4 is hydrogen, or (CrCaj-alkyl or (Ci-CO-alkenyi, each substituted by m radicals from the group consistîng of fluorine, chlorine and (Ci-C2)-alkoxy;
Y is oxygen;
W is oxygen;
Z is a Z-l, Z-4 or Z-6 group:
Z-4 Z-6 where the arrow in each case represents a bond to the group C=W of the formula (I);
X2, X4 and X6 are each hydrogen;
X3 and X3 are each fluorine; and m is the index 0, 1, 2 or 3.
In a 20th embodiment of the présent invention,
G is a group of the formula NRnR12;
R1 and R2 are each Îndependently hydrogen, fluorine, chlorine or cyano, or are (CrC,-i)-alkyl or (Ci-Csj-alkoxy, each substituted by m radicals from the group consistîng of fluorine, chlorine, bromine and cyano;
R3 is cyano, or (Cj-Cy-alkyl, (Ca-C+j-cycloalkyl, (C2-C3)-alkenyl or (Ci-Cf)-alkoxy, each substîtuted by m radicals from the group consisting of fluorine, chlorine, bromine, cyano, (Ci-Caj-alkoxy and hydroxy;
Y is oxygen;
W is oxygen;
is a Z-l to Z-12 group, where Z-l to Z-12 are defined as follows:
where the arrow in each case represents a bond to the group C=W of the formula (I);
X2, X4 and X6 are each independently hydrogen, fluorine, chlorine, bromine or cyano, or are methyl or methoxy, each substîtuted by m radicals from the group consisting of fluorine and chlorine;
X3 and X5 are each independently hydrogen, fluorine, cyano or methyl; and
R5 is (Ci-Ctj-alkyl or (Cj-Gj-cycloalkyl, each substîtuted by m radicals from the group consisting of fluorine and chlorine;
Rfi is hydrogen or R5;
R7 is hydrogen, or (Ci-Cfi)-alkyl or (CrQj-cycloalkyl, each substituted by m radicals from the group consisting of fluorine, chlorine and (Ci-C2)-alkoxy;
R8 is hydrogen, or (Ci-Cs)-alkyl or (C3-C6)-cycloalkyl, each substituted by m radicals from the group consisting of fluorine, chlorine and (CrC2)-alkoxy;
R11 is hydrogen, or (Ci-C3)-alkyl or (CrCej-cycloalkyl, each substituted by m radicals from the group consisting of fluorine and chlorine;
R12 is preferably hydrogen, cyano, OR7, S(O)n R5, SO2NR6R7, COR6, NRf’R8, NR6COR8 or NR6SO2Rs, or (Ci-C6)-alkyi, (C3-C6)-cycloalkyl, (C2-C3)-alkenyl or (C2-C3)-alkynyl, each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, cyano, OR7, S(O)„R5, NR6R8 and NR6CO2RB;
or
R11 and R12 together with the nitrogen atom to which they are attached form a saturated, partialiy or fully unsaturated five-, six- or seven-membercd ring which is optionally mono- to hexasubstituted by radicals from the group consisting of halogen, cyano, nitro, (Ci-C<0alkyl, halo-(Ci-C6)-alkyI, oxo, OR7, CO2R8 and NR6SO2R8 and which, in addition to this nitrogen atom, contains r carbon atoms, o oxygen atoms, p sulfur atoms and q éléments from the group consisting of NR7 and NCOR7 as ring atoms;
the index m is 0, 1, 2 or 3;
the index n is 0, 1 or 2;
the index o is 0, 1 or 2;
the index p is 0 or 1;
the index q is 0 or 1; and the index r is 3, 4 or 5.
In a 2 Ist embodiment of the présent invention,
G is a group of the formula NRHR12;
R1 and R2 are each hydrogen;
R3 is (Ci-C3)-alkyl, (Cj-CQ-cycloalkyl, (C2-C3)-alkenyl or (Ci-C3)-aikoxy, each substituted by m radicals from the group consisting of fluorine, chlorine and (Ci-C2)-alkoxy;
Y is oxygen;
W is oxygen;
Z îs a Z-l, Z-4 or Z-6 group:
Z-4 Z-6 where the arrow in each case represents a bond to the group C=W of the formula (I);
X2, X4 and X6 are each independently hydrogen or fluorine;
X3 and X5 are each independently hydrogen, fluorine, cyano or rnethyl;
R5 is (Ci-CQ-alkyl or (C3-C6)-cycloalkyl, each substituted by m radicals from the group consisting of fluorine and chlorine;
Rfi is hydrogen or R5;
R7 is hydrogen, or (Ci-Cft)-alkyl or (C3-C6)-cycloalkyl, each substituted by m radicals from the group consisting of fluorine, chlorine and (Ci-C2)-alkoxy;
Rs is hydrogen, or (Ci-C(,)-alkyl or (C3-C6)-cycloalkyl, each substituted by m radicals from the group consisting of fluorine, chlorine and (Ci-C2)-aikoxy;
R11 is hydrogen or (Ci-C3)-alkyl;
R12 is OR7, S(O)nR5, SO2NR&R7, or (Ci-C6)-alkyl substituted in each case by m radicals from the group consisting of fluorine, chlorine, cyano, OR7 and S(O)nR , or
R11 and R12 together with the nitrogen atom to which they are bonded form a saturated or partly or fully unsaturated five- or six-membered ring which is optionally mono- to trisubstituted by radicals from the group consisting of halogen, (Ci-Côj-alkyl, halo-(C]-Cô)-alkyl and oxo and which, in addition to that nitrogen atom, contains r carbon atoms, o oxygen atoms, p sulfur atoms and q éléments from the group consisting of N R7 and NCOR7 as ring atoms;
the index m is 0, 1, 2 or 3;
the index n is 0, 1 or 2;
the index o is 0, 1 or 2;
the index p is 0 or 1;
the index q is 0 or 1; and the index r is 3, 4 or 5.
In a 22nd embodiment of the présent invention,
G is a group of the formula NRHR12;
R1 and R2 are each hydrogen;
R3 is (Ci-Cft-alkyl, (Cj-C^-cycloaîkyl, (Cz-Caj-alkenyl or (Ci-Cft-alkoxy, each substituted by m radicals from the group consisting of fluorine, chlorine and (Ci-Cjj-alkoxy;
Y is oxygen;
W is oxygen;
Z is a Z-l, Z-4 or Z-6 group:
2-1 Z-4 Z-6 where the arrow in each case represents a bond to the group C=W of the formula (1);
X2, X4 and X6 are each hydrogen;
X3 and X5 are each fluorine;
R5 is (Ci-C6)-alkyl or (C3-Cfi)-cycloalkyl, each substituted by m radicals from the group consistîng of fluorine and chlorine;
R6 is hydrogen or R5;
R7 is hydrogen, or (Ct-CcJ-alkyl or (C3-C6)-cycloalkyl, each substituted by m radicals from the group consistîng of fluorine, chlorine and (Ci-C2)-aikoxy;
R8 is hydrogen, or (Ci-CrO-alkyl or (C3-C6)-cycioalkyl, each substituted by m radicals from the group consistîng of fluorine, chlorine and (Cj-C2)-alkoxy;
R is hydrogen;
R12 is OR7, S(O)„R5, SO2NR6R7, or (Ci-Cft)-alkyl substituted in each case by m radicals from the group consistîng of fluorine, chlorine, cyano, OR7 and S(O)nR5;
or
R11 and R12 together with the nitrogen atom to whîeh they are bonded form a saturated or partly or fully unsaturated five- or six-membered ring which is optionally mono- to trisubstituted by radicals from the group consistîng of halogen, (Ci-Ce)-alkyl, halo-(Ci-C6)-alkyl and oxo and which, in addition to that nitrogen atom, contains r carbon atoms, o oxygen atoms, p sulfur atoms and q éléments from the group consistîng of NR7 and NCOR7 as ring atoms;
the index m is 0, 1,2 or 3;
the index n is 0, 1 or 2;
the index o is 0, 1 or 2;
the index p is 0 or 1;
the index q is 0 or 1; and the index r is 3,4 or 5.
In a 23rd embodiment of the present invention, the herbicidal composition, as well as at least one component (B) as defined above, preferably comprises (A) one or more compounds [component (A)] of the general formula (I) [herbicides (A)] according to Table 1.
Table 1: IUP AC names and structural formulae of the preferred compounds of the formula (1) (herbicide (A))
| Compound No. | IUPAC name | Structural formula |
| Al | methyl (lS,4R)-4-[[[(5S)-3-(3,5di fluoropheny l)-5-viny Ï-4H-1,2-oxazol-5 yl]carbonyl]amino]cyclopent-2-ene-lcarboxylate | Tl /=Z / \ iz^O O /°< |
| A2 | ethyl ( lS,4R)-4-[[[3-(3,5-dinuoTOphenyl)5-methoxy-4H-l,2-oxazol-5yl]carbonyl]amino]cyclopent-2-ene-lcarboxylate | Γ\ OXZI L° o^\ x \ / Z --LL LL· |
| A3 | 2-methoxyethyl (lS,4R)-4-[[[(5R)-3-(3cyano-5-fluorophenyl)-5-(trifluoromethyl)4H-l,2-oxazoi-5yl]carbonyl]amino]cyclopent-2-ene-lcarboxylate | °\VZT 1 U JA?......riZ o \ \ 1 / 4 O-U. 1___ |
| A4 | methyl (4S)-4-[[[3-(3,5-difluorophenyl)-5methyl-4H-l,2-oxazol-5yl]carbonyl]amino]cyclopentene-lcarboxylate | °w / / ° n \ / Ζ=Ά LL· |
| A5 | methyl (3S)-3-[[[(5R)-3-(3,5dîfluorophenyl)-5-methyl-4H-l,2-oxazol5-yi]carbonyl]amino]cyclopentene-lcarboxylate | N-° 0 [J h T F |
| A6 | 3-(3,5-di Π uoropheny 1)-N- [( 1 R,4S)-4(oxazinan-2-ylcarbonyl)cycIopent-2-en-lyI]-5-(trifluoromethyl)-4H-l,2-oxazole-5carboxamide | N-O 0 f zx TT 1 N—<r 1 H fZf h F 4 ° |
| Compound No. | 1UPAC name | Structural formula | ||
| A7 | 3-(3,5-difluoropheny])-N-[(lR,4S)-4'(propylsulfonylamino)carbonyljcyclopent2-en-l-yl]-5-(trifluoromethyI)-4H-l,2oxazole-5-carboxamide | F | F | O ,--- O zz __f X O ZI u. J Z. u. \ / z=/ |
| A8 | (lS,4R)-4-[[(5R)-3-(3,5-difluorophenyl)-5methy 1-4 H-isoxazole-5carbonyl]amino]cyclopent-2-ene-lcarboxylic acid | F | 0 F | N-Λ fi 'T % N ^1 (r OH |
In Table 1, the compounds are identified by the Chemical formula of the main component, this component being présent in a Chemical purity of preferably at least 95 per cent by weight of the compound. The compounds can naturally also be used with lower purities. Especially when secondary components of the 5 compounds consist entirely orpredominantly of stereoisomers of the respective compounds (A), efficacies are achieved on application. Preferred herbicides (A) are therefore also mixtures of two or more compounds (A) of the invention.
When the stereochemical orientation at a carbon atom is defïned in Table 1, the main component of the compound is a stereoisomer or stereoisomer mixture having the R or S configuration at the carbon atom 10 in question.
If no stereochemistry is defïned, the compound is a racemate. If there are multiple stereocentres and the configuration of each is identified as R or S, these are compounds having the stated stereochemistry at the centres in question.
If no R or S configuration is specified for multiple centres, the compounds are raceinic mixtures, i.e. 15 mirror-image stereoisomers (enantiomers of a pair of enantiomers) présent therein are présent in equal proportions in the mixture. Unless stated specîfically, in Table 1, the diastereomeric components are présent approximately in equal proportions in the case of racemic compounds (A) having multiple stereocentres. For practical use, however, mixtures of diastereomers having different proportions of the diastereomeric components exist in the case of racemic compounds having multiple stereocentres.
It is préférable here that the respective compounds listed are also présent in a stereochemical purity of 60% to 100%, preferably 70-100%, especially 80% to 100%.
Preference is also given to the detailed mixtures of stereoisomerîc compounds (A).
The compounds of the formula (I) are known from the application having reference PCT/EP2019/051333, which was yet to be published at the priority date of the présent application, and can be prepared by the processes described therein.
The application rates ofthe herbicides (A) are in the range of 0.01 to 2000 g of active substance per hectare (g a.i./ha hereinafter), preferably 0.02 to 1000 g a.î./ha, especially 0.5 to 750 g a.i./ha. In the combinations of the invention, within the scope of the application rates mentioned by comparison to individual application, required application rates of the respective active ingrédient are usually lower, preferably 0.01 to 1000 g a.i./ha, especially 0.02 to 500 g a.i./ha, and most preferably 5 to 250 g a.i./ha.
Suitable combination partners (B) [= component (B) or herbicides (B)] are in principle ail active ingrédients from subgroups (Bl) to (Bll), with the naming of the active herbicidal ingrédients largely by their common name (in the English notation) according to the reference The Pesticide Manual 14th ed., British Crop Protection Council 2006, abbreviated to PM, or by their Chemical name according to the standard nomenclatures (1UPAC or Chemical Abstracts).
However, some herbicides (B) hâve surprisingly been found to be particularly good combination partners. The preferred, more preferred and most preferred herbicides (B) are listed hereinafter as further embodiments of the présent invention.
In a 24th embodiment of the présent invention, preference is given to the active herbicidal ingrédients (Bl):
| (B1.2) (BE4) (B1.7) | bicyclopyrone, clethodim, mesotrione. |
| (B1.8) (B 1.10) | pinoxaden, sethoxydim, |
| (Bl.ll) (B1.14) (B 1.16) | sulcotrione, tembotrione and tralkoxydim. |
Particular preference is given to the active herbicidal ingrédients
| (B1.7) (B1.8) (B1.14) | mesotrione, pinoxaden and tembotrione. |
In a 25th embodiment of the present invention, preference is given to the active herbicidal ingrédients (B2):
| (B2.1) | acetochlor. |
| (B2.3) | amidosulfuron, |
| (B2.4) | asulam, |
| (B2.6) | beflubutamid, |
| (B2.10) | chlorimuron, |
| (B2.12) | chlorsulfuron. |
| (B2.14) | cloransulam. |
| (B2.17) | dielosulam, |
| (B2.18) | diflufenican, |
| (B2.23) | ethoxysulfuron. |
| (B2.24) | flazasulfuron, |
| (B2.25) | florasulam, |
| (B2.26) | flucarbazone. |
| (B2.28) | flufenacet, |
| (B2.29) | flumetsulam, |
| (B2.30) | flupyrsulfuron. |
| (B2.31) | foramsulfuron. |
| (B2.34) | iodosulfuron, |
| (B2.37) | mesosulfuron, |
| (B2.40) | metolachlor, |
| (B2.41) | metosulam, |
| (B2.42) | metsuifuron, |
| (B2.46) | penoxsulam, |
| (B2.49) | picolînafen. |
| (B2.56) | propoxycarbazone. |
| (B2.58) | propyzamide, |
| (B2.59) | prosulfocarb, |
| (B2.60) | prosulfuron, |
| (B2.62) | pyroxsulam, |
| (B2.63) | rimsulfuron, |
| (B2.64) | S-metolachlor, |
| (B2.65) | sulfometuron. |
| (B2.66) | sulfosulfuron. |
| (B2.68) | thiencarbazone, |
| (B2.69) | thifensulfuron, |
(B2.72) tribenuron, (B2.76) esprocarb, (B2.78) tri-alla te.
Particular preference is given to
| (B2.3) | amidosulfuron. |
| (B2.18) | diflufenican, |
| (B2.24) | flazasulfuron, |
| (B2.25) | florasulam. |
| (B2.26) | flucarbazone, |
| (B2.28) | flufenacet, |
| (B2.31) | foramsulfuron, |
| (B2.34) | iodosulfuron, |
| (B2.37) | mesosulfuron, |
| (B2.58) | propyzamîde. |
| (B2.68) | thiencarbazone, |
| (B2.69) | thifensulfuron, |
| (B2.72) | tribenuron. |
In a 26th embodiment of the présent invention, preference is given to the active herbicidal ingrédients (B3):
(B3.1) (B3.4) bromoxynil and ioxynil.
In a 27th embodiment of the présent invention, preference is given to the active herbicidal ingrédients (B4):
| (B4.2) | amitrole, |
| (B4.8) | carfentrazone, |
| (B4.10) | Îmazamethabenz, |
| (B4.ll) | imazamox, |
| (B4.12) | imazapic, |
| (B4.13) | imazapyr, |
| (B4.15) | imazethapyr, |
| (B4.17) | isoxaben, |
| (B4.18) | isoxaflutole, |
| (B4.21) | pyrafiufen, |
| (B4.22) | pyrasulfotole. |
(B4.25) pyroxasulfone and (B4.28) topramezone, (B4.33) flupoxam.
Particular preference is given to (B4.18) isoxaflutole and (B4.25) pyroxasulfone, (B4.22) pyrasulfotole.
in a 28th embodiment of the présent invention, preference is given to the active herbicidal ingrédients
| 5 | (B5): | |
| (B5.1) | am i nocy cl opy rach 1 o r, | |
| (B5.2) | aminopyralid, | |
| (B5.3) | benazolin. | |
| (B5.5) | bentazone. | |
| (B5.7) | bixlozone, | |
| (B5.12) | cinidon, | |
| (B5.13) | cinmethylin, | |
| (B5.14) | clomazone, | |
| (B5.21) | ethofumesate, | |
| (B5.22) | flamprop, | |
| (B5.23) | florpyrauxifen, | |
| (B5.26) | flumioxazin, | |
| (B5.27) | flurîdone, | |
| (B5.28) | flurochloridone, | |
| (B5.29) | flurtamone, | |
| (B5.31) | halauxifen, | |
| (B5.32) | indanofan, | |
| (B5.37) | paraquat, | |
| (B5.38) | pelargonic acid, | |
| (B5.39) | pendimethalin. | |
| (B5A5) | triafamone and | |
| (B5.46) | trifluralîn, | |
| (B5.47) | 4-aiïiino-3-chloro-5-fIuoro-6-(7-fluoro-lH- | |
| îndol-6-yl)pyridine-2-carboxylic acid. | ||
| (B5.48) | cyclopyrimorate, | |
| (B5.49) | diquat, |
(B5.50) oxaziclomefone.
Particular preference is given to (B5.7) bixlozone,
| (B5.23) (B5.31) (B5.38) | florpyrauxifen, halauxifen and pe largo nie acid. |
In a 29th embodiment of the présent invention, preference is given to the active herbicidal ingrédients (B6);
(B6.2) clopyralid,
| (B6.3) | dicamba, |
| (B6.4) | fluroxypyr and |
| (B6.5) | picloram. |
Particular preference is given to
| (B6.2) (B6.3) (B6.4) | clopyralid, dicamba and fluroxypyr. |
In a 30th embodiment of the présent invention, preference is given to the active herbicidal ingrédients (B7):
(B7.2) bialaphos,
| (B7.4) (B7.5) (B7.7) | glufosinate, glyphosate and sulfosate. |
Particular preference is given to (B7.4) glufosinate and (B7.5) glyphosate.
In a 31st embodiment of the présent invention, preference is given to the active herbicidal ingrédients (B8);
(B8.1) 2,4-D,
| (B8.3) | 2,4-DP, |
| (B8.5) | aclonifen, |
| (B8.8) | clodinafop, |
| P (B8.ll) (B8.13) (B8.20) (B8.22) (B8.26) (B8.27) | diclofop, fenoxaprop, MCPA, mecoprop, quizalofop and quizalofop. |
Particular preference is given to
| (B8.1) (B8.5) | 2,4-D and aclonifen. |
In a 32nd embodiment of the présent invention, preference is given to the active herbicidal ingrédients
| 5 (B9): (B9.1Ü) (B9.ll) (B9.13) (B9.14) | saflufenacil, terbacil, tnfiudimoxazin and ethyl [3-[2-chloro-4-fluoro-5-(l-methyl-6- trifluoromethy 1 -2,4-dioxo-1,2,3,4- tetrahydropyrimidin-3-yl)phenoxy]-2- pyridyloxy]acetate. |
Most preferred is (B9.10) saflufenacil.
In a 33rd embodiment of the présent invention, preference is given to the active herbicidal ingrédients (B10):
| (B10.1) (B 10.2) (B10.5) (B 10.8) (B10.9) (B10.10) (B10.il) (B10.12) (B10.13) | chlorobromuron, chlorotoluron, diuron, isoproturon, linuron, methabenzthiazuron, metobromuron, metoxuron and monolinuron. |
In a 34th embodiment of the présent invention, preference is given to the active herbicidal ingrédients (Bll):
| (Bll.l) | ametryne. |
| (B 11.2) | atrazine, |
| (B 11.5) | hexazinone, |
| (B11.6) | indaziflam, |
| (B11.8) | metribuzin. |
| (B11.12) | simazine, |
| (B11.15) | terbuthylazine and |
| (B11.16) | terbutryne. |
Particular preferetice is given to
| (B 11.5) (B11.6) (B11.8) | hexazinone, indaziflam and metribuzin. |
In a 35th embodiment of the présent invention, preference is given to the active hcrbicidal ingrédients (Bl)to(Bll):
| (B1.2) | bicyclopyrone, |
| (B1.4) | clethodim, |
| (B1.7) | mesotrione, |
| (B1.8) | pinoxaden, |
| (B1.10) | sethoxydim, |
| (Bl.ll) | sulcotrione, |
| (B1.14) | tembotrione, |
| (B1.16) | tralkoxydim; |
| (B2.1) | acetochlor, |
| (B2.3) | amidosulfuron. |
| (B2.4) | asulam. |
| (B2.6) | beflubutamid, |
| (B2.10) | chlorimuron, |
| (B2.12) | chlorsulfuron, |
| (B2.14) | cloransulam, |
| (B2.17) | diclosulam. |
| (B2.18) | diflufenican, |
| (B2.23) | ethoxysulfuron, |
| (B2.24) | flazasulfuron, |
| (B2.25) | florasulam. |
| (B2.26) (B2.28) (B2.29) (B2.30) (B2.31) (B2.34) (B2.37) (B2.40) (B2.41) (B2.42) (B2.46) (B2.49) (B2.56) (B2.58) (B2.59) (B2.60) (B2.62) (B2.63) (B2.64) (B2.65) (B2.66) (B2.68) (B2.69) (B2.72) (B2.76) (B2.78) | flucarbazone, flufenacet, flumetsulam, flupyrsulfuron, foramsulfuron, iodosulfuron, mesosulfuron, metolachlor, metosuiam, metsulfuron, penoxsulam, picolinafen, propoxycarbazone, propyzamide, prosulfocarb, prosuifuron, pyroxsulam, rimsulfuron, S-metolachlor, sulfometuron, sulfosulfuron, thiencarbazone, thifensulfuron, tribenuron, esprocarb, tri-allate; |
| (B3.1) (B3.4) | bromoxynîl, ioxynil; |
| (B4.2) (B4.8) (B4.10) (B4.ll) (B4.12) (B4.13) (B4.15) | amitrole, carfentrazone, imazamethabenz, imazamox, imazapic, imazapyr, îmazethapyr, |
| (B4.17) (B4.18) (B4.21) (B4.22) (B4.25) (B4.28) (B4.33) | isoxaben, isoxaflutoie, pyrafiufen, pyrasulfotole, pyroxasulfone, topramezone, flupoxam; |
| (B5.1) (B5.2) (B5.3) (B5.5) (B5.7) (B5.12) (B5.13) (B5.14) (B5.21) (B5.22) (B5.23) (B5.26) (B5.27) (B5.28) (B5.29) (B5.31) (B5.32) (B5.37) (B5.38) (B5.39) (B5.45) (B5.46) (B5.47) | aminocyclopyrachlor, aminopyralid, benazolin, bentazone, bîxlozone, cinidon, cinmethylin, clomazone, ethofumesate, flamprop, florpyrauxifen, flumioxazin, fluridone, flurochloridone, flurtamone, halauxifen, indanofan, paraquat, pelargonic acid, pendimethalin, triafamone, trîfluralin, 4-amino-3-chIoro-5-fluoro-6-(7fluoro-lH-indol-6-yl)pyridine-2carboxylic acid, |
| (B5.48) (B5.49) (B5.50) | cyclopyrîmorate, diqual, oxaziclomefone; |
| (B6.2) (B6.3) (B6.4) (B6.5) | clopyralid, dicamba, fluroxypyr, picloram; |
| (B7.2) (B7.4) (B7.5) (B7.7) | bialaphos, glufosinate, glyphosate, sulfosate; |
| (B8.1) (B8.3) (B8.5) (B8.8) (B8.ll) (B8.13) (B8.20) (B8.22) (B8.26) (B8.27) | 2,4-D, 2,4-DP, acionifen, clodinafop, diclofop, fenoxaprop, MCPA, mecoprop, quizalofop, quizalofop; |
| (B9.10) (B9.ll) (B9.13) (B9.14) | saflufenacil, terbacil, trifludimoxazin, ethyl [3-[2-chloro-4-fluoro-5-(lmethyI-6-trifluoromethyl-2,4-dîoxo1,2,3,4-tetrahydropy rimidi 11-3yl)phenoxy]-2-pyridyloxyJacetate; |
| (B10.1) (B 10.2) (B10.5) (B10.6) (B10.8) (B10.9) (B10.10) (B10.il) | chlorobromuron, chlorotoluron, diuron, diflufenzopyr, isoproturon, linuron, methabenzthiazuron, metobromuron, |
| (B 10.12) (B10.13) | metoxuron, monolinuron; |
| (El 1.1) (B11.2) (B11.5) (B11.6) (B 11.8) (B11.12) (B11.15) (B11.16) | ametryne, atrazine, hexazinone, indaziflam, metribuzin, simazine, terbuthylazine, terbutryne. |
Particular preference is given to:
| (B1.7) | mesotrione. |
| (B1.8) | pinoxaden, |
| (B1.14) | tembotrione; |
| (B2.3) | amidosulfuron. |
| (B2.18) | diflufenican, |
| (B2.24) | flazasulfuron, |
| (B2.25) | florasulani. |
| (B2.26) | flucarbazone, |
| (B2.28) | flufenacet. |
| (B2.31) | foramsulfuron. |
| (B2.34) | iodosulfuron. |
| (B2.37) | mesosulfuron. |
| (B2.58) | propyzamide, |
| (B2.68) | thiencarbazone, |
| (B2.69) | thifensulfuron, |
| (B2.72) | tribenuron; |
| (B3.1) | bromoxynil, |
| (B4.18) | isoxaflutole. |
| (B4.22) | pyrasulfotole, |
| (B4.25) | pyroxasulfone; |
| (B5.7) (B5.23) (B5.38) | bixlozone, florpyrauxifen, pelargonic acid, |
| (B6.2) (B6.3) (B6.4) | clopyralid, dicamba, fluroxypyr, |
| (B7.4) (B7.5) | glufosinate, glyphosate, |
| (B8.1) (B8.5) | 2,4-D, aclonifen, |
| (B9.10) | saflufenacil, |
| (B11.5) (B 11.6) (B11.8) | hexazinone, îndaziflam, metribuzîn. |
In the context of the présent invention, it is possible to combine the individuel preferred, more preferred and most preferred embodiments with one another as desired. This means that herbicidal compositions comprising (A) one or more compounds of the general formula (I) or agrochemically acceptable salts thereof [component (A)] and (B) one or more herbicides [component (B)] selected from the group of the active herbicidal ingrédients (Bl) to (B 11) are encompassed by the présent invention, in which any desired preferred, more preferred and most preferred embodiments disclosed can be combined with one another as detailed above.
Some binary compositions comprising (A) one or more herbicidally active compounds (A) of the general formula (I) or agrochemically acceptable salts thereof [herbicides (A)] and a herbicide (B) hâve surprisingly been found to be particularly advantageous. The preferred, more preferred and most preferred binary Systems are listed hereinafter as further embodiments of the présent invention.
In a 36th embodiment of the présent invention, the composition preferably comprises (A) a compound of the general formula (I) or agrochemically acceptable salts thereof [herbicides (A)]
in which
G is a group of the formula OR4;
R1 and R2 are each hydrogen;
R3 is (Cj-C3)-alkyl, (C3-C4)-cycloalkyl, (C2-C3)-alkenyl or (CrC3)-alkoxy, each substituted by m radicals from the group consisting of fluorine, chlorine and (Ci-C2)-alkoxy;
R4 is hydrogen, or (Ci-C3)-aIkyl or (C2-C4)-alkenyl, each substituted by m radicals from the group consisting of fluorine, chlorine and (Ci-C2)-alkoxy;
Y is oxygen;
W is oxygen;
Z is a Z-l, Z-4 or Z-6 group:
Z-1
Z-6 where the arrow in each case represents a bond to the group C=W of the formula (I);
X2, X4 and Xfi are each independentiy hydrogen or fluorine;
X3 and X5 are each independentiy hydrogen, fluorine, cyano or methyl; and the index m is 0, 1, 2 or 3;
and (B) a herbicide [component (B)] from the group consisting of
| (B1.2) (B1.4) (B1.7) (B1.8) (B1.10) (Bl.ll) (B1.14) (B1.16) | bicyclopyrone, clethodim, mesotrione, pinoxaden, sethoxydim, sulcotrione, tembotrione, tralkoxydim; |
| (B2.1) (B2.3) (B2.4) (B2.6) (B2.10) (B2.12) (B2.14) (B2.17) (B2.18) (B2.23) (B2.24) (B2.25) (B2.26) (B2.28) (B2.29) (B2.30) (B2.31) (B2.34) (B2.37) (B2.40) (B2.41) (B2.42) (B2.46) (B2.49) (B2.56) (B2.58) (B2.59) (B2.60) | acetochlor, amidosulfuron, asulam, beflubutamid, chlorimuron, chlorsulfuron, cloransulam, diclosulam, diflufenican, ethoxysulfuron, flazasulfuron, fiorasulam, flucarbazone, flufenacet, flumetsulam, flupyrsulfuron, foramsulfnron, iodosulfuron, mesosulfuron, metolachlor, metosulam, metsulfuron, penoxsulam, picolinafen, propoxycarbazone, propyzamide, prosulfocarb, prosulfuron. |
| (B2.62) (B2.63) (B2.64) (B2.65) (B2.66) (B2.68) (B2.69) (B2.72) (B2.76) (B2.78) | pyroxsulam, rimsulfuron, S-metolachlor, sulfometuron, sulfosulfuron, thiencarbazonc, thifensulfuron, tribenuron, esprocarb, tri-allate; |
| (B3.1) (B3.4) | bromoxynîl, îoxynil; |
| (B4.2) (B4.8) (B4.10) (B4.ll) (B4.12) (B4.13) (B4.15) (B4.17) (B4.18) (B4.21) (B4.22) (B4.25) (B4.28) (B4.33) | amitrole, carfentrazone, imazamethabenz, imazamox, imazapic, imazapyr, imazethapyr, isoxaben, isoxaflutole, pyraflufen, pyrasulfotole, pyroxasulfone, topramezone, flupoxain; |
| (B5.1) (B5.2) (B5.3) (B5.5) (B5.7) (B5.12) (B5.13) (B5.14) | aminocyclopyrachlor, aminopyralid, benazoliii, bentazone, bîxlozone, cinidon, cinmethylin, clomazone, |
| (B5.21) (B5.22) (B5.23) (B5.26) (B5.27) (B5.28) (B5.29) (B5.31) (B5.32) (B5.37) (B5.38) (B5.39) (B5.45) (B5.46) (B5.47) | ethofumesate, flamprop, florpyrauxifen, flumioxazin, fluridone, flurochloridone, flurtamone, halauxifen, indanofan, paraquat, pelargonic acid, pendimethalin, triafamone, trifluralin, 4-amino-3-chloro-5-fluoro-6-(7fluoro-lH-indol-6-yl)pyridine-2carboxylic acid, |
| (B5.48) (B5.49) (B5.50) | cy c 1 op y ri morat e, diquat, o x az icio me f o ne ; |
| (B6.2) (B6.3) (B6.4) (B6.5) | clopyralid, dicamba, fluroxypyr, picloram; |
| (B7.2) (B7.4) (B7.5) (B7.7) | bialaphos, glufosinate, glyphosate, sulfosate; |
| (B8.1) (B8.3) (B8.5) (B8.8) (B8.ll) (B8.13) | 2,4-D, 2,4-DP, aclonifen, clodinafop, diclofop, fenoxaprop, |
| (B8.20) (B8.22) (B8.26) (B8.27) | MCPA, mecoprop, quizalofop, quizalofop; |
| (B9.10) (B9.ll) (B9.13) (B9.14) | saflufenacil, terbacil, trifludimoxazin, ethyl [3-[2-chloro-4-fluoro-5-(lmethyl-6-trifluoromethyl-2,4-dioxol,2,3,4-tetrahydropyrimidin-3yl)phenoxy]-2-pyridyloxy]acetate; |
| (B10.1) (B10.2) (B10.5) (B 10.6) (B10.8) (B10.9) (B10.10) (B10.il) (B10.12) (B 10.13) | chlorobromuron, chlorotoluron, diuron, diflufenzopyr, isoproturon, linuron, methabenzthiazuron, metobromuron, metoxuron, monolinuron; |
| (B 11.1) (B'11.2) (B11.5) (B 11.6) (BU.8) (B11.12) (BU. 15) (BU.16) | ametryne, atrazine, hexazinone, indaziflam, metribuzin, simazine, terbuthylazine, terbutryne. |
In a 37th embodiment of the présent invention, the composition preferably comprises (A) a compound of the general formula (I) or agrochemically acceptable salts thereof [herbicides (A)]
Y
in which
G is a group of the formula OR4;
R1 and R2 are each hydrogen;
R3 is (Ci-C3)-alkyl, (C3-Ci)-cycloalkyl, (C2-C3)-alkenyl or (Ci-C3)-alkoxy, each substituted by m radicals from the group consisting of fluorine, chlorine and (Ci-C2)-alkoxy;
R4 is hydrogen, or (Ci-C3)-alkyl or (C2-C4)-alkenyl, each substituted by m radicals from the group consisting of fluorine, chlorine and (Ci-C2)-alkoxy;
Y is oxygen;
W is oxygen;
Z is a Z-l, Z-4 or Z-6 group:
Z-1
Z-4
Z-6 where the arrow in each case represents a bond to the group C=W of the formula (I);
X2, X4 and X6 are each hydrogen;
X3 and X5 are each fluorine; and the index m is 0, 1, 2 or 3;
and (B) a herbicide [component (B)] from the group consisting of
| (B1.7) (B1.8) (B 1.14) | mesotrione, pinoxaden, lembotrione, |
| (B2.3) (B2.18) (B2.24) (B2.25) (B2.26) (B2.28) (B2.31) (B2.34) (B2.37) (B2.58) (B2.68) (B2.69) (B2.72) | amidosuifuron, diflufenican, flazasulfuron, florasulam, flucarbazone, flufenacet, foramsulfuron, iodosulfuron, mesosulfuron, propyzamide, thiencarbazone, thifensulfuron, tribenuron. |
| (B3.1) | bromoxynil, |
| (B4.18) (B4.22) (B4.25) | isoxaflutole, pyrasulfotole, pyroxasulfone. |
| (B5.7) (B5.23) (B5.31) (B5.38) | bixlozone, florpyrauxifeti, halauxifen, pelargonic acid. |
| (B6.2) (B6.3) (B6.4) | clopyraJid, dicamba, fluroxypyr, |
| (B7.4) (B7.5) | glufosinate, glyphosate. |
| (B8.1) | 2,4-D, |
| (B8.5) | aclonifen, |
| (B9.10) | saflufenacil, |
| (B11.5) | hexazinone. |
| (B 11.6) | indaziflam, |
| (B 11.8) | metribuzin. |
In a 38th embodiment of the présent invention, the composition preferably comprises (A) a compound of the general formula (I) or agrochemically acceptable salts thereof [herbicides (A)]
Y
in which
G is a group of the formula NRnR12;
R1 and R2 are each hydrogen;
R3 îs (Ci-Ca)-alkyl, (Cj-C^-cycloalkyl, (C2-C3)-alkenyl or (Ci-CQ-alkoxy, each substituted by m radicals from the group consisting of fluorine, chlorine and (Ct-C2)-alkoxy;
Y is oxygen;
W is oxygen;
Z is a Z-l, Z-4 or Z-6 group:
Z-1
Z-4
Z-6 where the arrow in each case represents a bond to the group C=W of the formula (I);
X2, X4 and X6 are each independently hydrogen or fluorine;
X3 and X5 are each independently hydrogen, fluorine, cyano or methyl;
R5 is (Ci-CrO-alkyi or (C3-Cf,)-cycloalkyl, each substituted by m radicals from the group consisting of fluorine and chlorine;
R6 is hydrogen or R5;
R7 is hydrogen, or (Ci-Cfi)-alkyl or (Cs-Csj-cycloalkyl, each substituted by m radicals from die group consisting of fluorine, chlorine and (Ci-C2)-alkoxy;
RK is hydrogen, or (Ci-CQ-alkyl or (C3-O,)-cycloalkyl, each substituted by m radicals from the group consisting of fluorine, chlorine and (Ci-C2)-alkoxy;
R11 is hydrogen or (Ci-C3)-alkyl;
R12 is OR7, 5(Ο)ηΚ5, SO2NRftR7, or (CrC6)-alkyl substituted in each case by m radicals from the group consisting of fluorine, chlorine, cyano, OR7 and S(O)nR5;
or
R11 and R12 together with the nitrogen atom to which they are bonded form a saturated or partly or fully unsaturated five- or six-membered ring which is optionally mono- to trisubstituted by radicals from the group consisting of halogen, (Ci-Côj-alkyl, haIo-(Ci-C6)-alkyl and oxo and which, in addition to that nitrogen atom, contains r carbon atoms, o oxygen atoms, p sulfur atoms and q éléments from the group consisting of NR7 and NCOR7 as ring atoms;
the index m is 0, 1, 2 or 3;
the index n is 0, 1 or 2;
the index o is ü, 1 or 2;
the index p is 0 or 1;
the index q is 0 or 1; and
the index r is 3, 4 or 5;
and (B) a herbicide [component (B)] from the group consisting of
| (B1.2) | bicyclopyrone, |
| (B1.4) | clethodim, |
| (B1.7) | mesotrione, |
| (B 1.8) | pînoxaden. |
| (B1.10) | sethoxydim, |
| (Bl.ll) | sulcotrione. |
| (B 1.14) | tembotrione. |
| (B1.16) | tralkoxydim; |
| (B2.1) | acetochlor. |
| (B2.3) | amidosulfuron, |
| (B2.4) | asulam, |
| (B2.6) | beflubutamid. |
| (B2.10) | chlorimuron. |
| (B2.12) | chlorsulfuron, |
| (B2.14) | cloransulam, |
| (B2.17) | dîclosulam, |
| (B2.18) | diflufenican. |
| (B2.23) | ethoxysulfuron, |
| (B2.24) | flazasulfuron. |
| (B2.25) | florasulam. |
| (B2.26) | flucarbazone, |
| (B2.28) | flufenacet. |
| (B2.29) | flumetsulam. |
| (B2.30) | flupyrsulfuron, |
| (B2.31) | foramsulfuron, |
| (B2.34) | iodosulfuron. |
| (B2.37) | mesosulfuron, |
| (B2.40) | metolachlor, |
| (B2.41) | metosuiam, |
| (B2.42) | metsulfuron. |
| (B2.46) (B2.49) (B2.56) (B2.58) (B2.59) (B2.60) (B2.62) (B2.63) (B2.64) (B2.65) (B2.66) (B2.68) (B2.69) (B2.72) (B2.76) (B2.78) | penoxsulam, picolinafen, propoxycarbazone, propyzamide, prosulfocarb, prosulfuron, pyroxsulam, rimsulfuron, S-metolachlor, sulfometuron, sulfosulfuron, thiencarbazone, thifensulfuron, tribenuron, esprocarb, tri-allate; |
| (B3.1) (B3.4) | bromoxynil, ioxynil; |
| (B4.2) (B4.8) (B4.10) (B4.ll) (B4.12) (B4.13) (B4.15) (B4.17) (B4.18) (B4.21) (B4.22) (B4.25) (B4.28) (B4.33) | amitrole, carfentrazone, imazamethabenz, imazamox, imazapic, imazapyr, imazethapyr, isoxaben, isoxaflutole, pyraflufen, pyrasulfotole, pyroxasulfone, topramezone, flupoxam; |
| (B5.1) (B5.2) | aminocyclopyrachlor, aminopyralid, |
| (B5.3) (B5.5) (B5.7) (B5.12) (B5.13) (B5.14) (B5.21) (B5.22) (B5.23) (B5.26) (B5.27) (B5.28) (B5.29) (B5.31) (B5.32) (B5.37) (B5.38) (B5.39) (B5.45) (B5.46) (B5.47) | benazolin, bentazone, bixlozone, cinidon, cinmethylin, clomazone, ethofumesate, flamprop, florpyrauxifen, flumioxazin, fluridone, flurochloridone, flurtamone, halauxifen, indanofan, paraquat, pelargonic acid, pendimethalin, triafamone, trifluralin, 4-amino-3-chloro-5-fluoro-6-(7fluoro-lH-indol-6-yI)pyriditie-2carboxylic acid, |
| (B5.48) (B5.49) (B5.5O) | cyciopyrimorate, diquat, oxaziclomefone; |
| (B6.2) (B6.3) (B6.4) (B6.5) | clopyralid, dicamba, fluroxypyr, picloram; |
| (B7.2) (B7.4) (B7.5) (B7.7) | bialaphos, glufosinate, glyphosate, sulfosate; |
| (B8.1) (B8.3) (B8.5) (B8.8) (B8.ll) (B8.13) (B8.20) (B8.22) (B8.26) (B8.27) | 2,4-D, 2,4-DP, aclonîfen, clodinafop, diclofop, fenoxaprop, MCP A, mecoprop, quizalofop, quizalofop; |
| (B9.10) (B9.ll) (B9.13) (B9.14) | saflufenacil, terbacil, trifludimoxazin, ethyl [3-[2-chloro-4-fluoro-5-(lmethyl-6-trifluoromethyl-2,4-dioxol,2,3,4-tetrahydropyrimidin-3yl)phenoxy]-2-pyridyloxy]acetate; |
| (B10.1) (B10.2) (B10.5) (B10.6) (B10.8) (B10.9) (B 10.10) (B 10.11) (B10.12) (B10.13) | chlorobromuron, chlorotoluron, diuron, diflufenzopyr, isoproturon, linuron, methabenzthiazuron, metobromuron, metoxuron, monolinuron; |
| (Bll.l) (BU. 2) (BU.5) (B11.6) (B11.8) (BU.12) (BU.15) | ametryne, atrazine, hexazinone, indaziflam, metribuzin, simazine, terbulhylazine, |
(B11.16) terbutryne.
Iti a 39th embodiment of the présent invention, the composition preferably comprises (A) a compound of the general formula (1) or agrochemically acceptable salis thereof [herbicides (A)]
Y
in which
G is a group of the formula NR11 R12;
R1 and R2 are each hydrogen;
R2 is (Ci-GO-alkyl, (Ca-C^-cycloalkyl, (C2-C3)-alkenyl or (Ci-Cft-alkoxy, each substituted by m radicals from the group consisting of fluorine, chlorine and (CrCij-alkoxy;
Y is oxygen;
W is oxygen;
Z is a Z-l, Z-4 or Z-6 group:
Z-4 Z-6 where the arrow in each case represents a bond to the group C-W of the formula (1);
X2, X4 and X6 are each hydrogen;
X3 and X5 are each fluorine;
R5 is (Ci-Cfi)-alkyl or (C3-Cfi)-cycloalkyl, each substituted by m radicals from the group consisting of fluorine and chlorine;
R is hydrogen or R5;
R7 is hydrogen, or (Ci-C6)-alkyl or (Cs-GQ-cycloalkyl, each substituted by m radicals from the group consisting of fluorine, chlorîne and (Ci-C2)-alkoxy;
R8 is hydrogen, or (CrQO-alkyl or (CvCej-cycloalkyl, each substituted by m radicals from the group consisting of fluorine, chlorîne and (CrC2)-alkoxy;
R11 is hydrogen;
R12 is OR7, S(O)nR5, SO2NRÛR7, or (Ci-Cfi)-alkyl substituted in each case by m radicals from the group consisting of fluorine, chlorîne, cyano, OR7 and S(O)nR5;
or
R and R12 together with the nitrogen atom to which they are bonded form a saturated or partly or fully unsaturated five- or six-membered ring which is optionally mono- to trisubstituted by radicals from the group consisting of halogen, (CrCc,)-alkyl, halo-(Ci-Cf>)-alkyl and oxo and which, în addition to that nitrogen atom, contains r carbon atoms, o oxygen atoms, p sulfur atoms and q éléments from the group consisting of NR7 and NCOR7 as ring atoms;
the index m is 0, 1, 2 or 3;
the index n is 0, 1 or 2;
the index o is 0,1 or 2;
the index p is 0 or 1;
the index q is 0 or 1; and the index r is 3, 4 or 5, and (B) a herbicide [component (B)[ from the group consisting of
| (B1.7) (B1.8) (B1.14) | mesotrione, pinoxaden, tembotrione. |
| (B2.3) (B2.18) (B2.24) (B2.25) (B2.26) (B2.28) (B2.31) (B2.34) (B2.37) (B2.58) (B2.68) (B2.69) (B2.72) | amidosulfuron, diflufenican, flazasulfuron, florasulam, flucarbazone, flufenacet, foramsulfuron, iodosulfuron, mesosulfuron, propyzamide, thiencarbazone, thifensulfuron, tribenuron. |
| (B3.1) | bromoxynil, |
| (B4.18) (B4.22) (B4.25) | isoxaflutole, pyrasulfotole, pyroxasulfone, |
| (B5.7) (B5.23) (B5.31) (B5.38) | bixlozone, ilorpyrauxifen, halauxifen, pelargonic acid, |
| (B6.2) (B6.3) (B6.4) | cîopyralid, dicamba, fluroxypyr, |
| (B7.4) (B7.5) | glufosinate, glyphosate, |
| (B8.1) | 2,4-D, |
| (B8.5) | aclonifen. |
| (B9.10) | saflufenacîl, |
| (B11.5) | hexazinone, |
| (ΒΓ1.6) | indaziflam, |
| (BU.8) | metribuzin. |
Particularly preferred compositions in the context of the présent invention are the compositions listed in 5 Tables 2.1 - 2.9 below:
Table 2.1: Particularly preferred binary compositions comprising (Al)
| Binary composition | Compound (A) | Compound (B) |
| ZI | Al | (B1.7) |
| Z2 | Al | (B1.8) |
| Z3 | Al | (B1.14) |
| Z4 | Al | (B2.3) |
| Z5 | Al | (B2.18) |
| Z6 | Al | (B2.24) |
| Z7 | Al | (B2.25) |
| Z8 | Al | (B2.26) |
| Z9 | Al | (B2.28) |
| Z10 | Al | (B2.31) |
| ZI1 | Al | (B2.34) |
| Z12 | Al | (B2.37) |
| Z13 | Al | (B2.68) |
| Z14 | Al | (B2.69) |
| Z15 | Al | (B2.72) |
| ZI 6 | Al | (B4.18) |
| Z17 | Al | (B4.25) |
| Z18 | Al | (B5.7) |
| Z19 | Al | (B5.23) |
| Z20 | Al | (B5.31) |
| Z21 | Al | (B5.38) |
| Binary composition | Compound (A) | Compound (B) |
| Z22 | Al | (B6.2) |
| Z23 | Al | (B6.3) |
| Z24 | Al | (B6.4) |
| Z25 | Al | (B7.4) |
| Z26 | Al | (B7.5) |
| Z27 | Al | (B8.1) |
| Z28 | Al | (B8.5) |
| Z29 | Al | (B9.10) |
| Z30 | Al | (B11.5) |
| Z31 | Al | (B 11.6) |
| Z32 ' | Al | (B 11.8) |
Table 2.2: Particularly preferred binary compositions comprising (A2)
| Binary composition | Compound (A) | Compound (B) |
| Z33 | A2 | (B1.7) |
| Z34 | A2 | (B1.8) |
| Z35 | A2 | (B1.14) |
| Z36 | A2 | (B2.3) |
| Z37 | A2 | (B2.18) |
| Z38 | A2 | (B2.24) |
| Z39 | A2 | (B2.25) |
| Z40 | A2 | (B2.26) |
| Z41 | A2 | (B2.28) |
| Z42 | A2 | (B2.31) |
| Z43 | A2 | (B2.34) |
| Z44 | A2 | (B2.37) |
| Z45 | A2 | (B2.68) |
| Z46 | A2 | (B2.69) |
| Z47 | A2 | (B2.72) |
| Z48 | A2 | (B4.18) |
| Z49 | A2 | (B4.25) |
| Z50 | A2 | (B5.7) |
| Z51 | A2 | (B5.23) |
| Z52 | A2 | (B5.31) |
| Z53 | A2 | (B5.38) |
| Binary composition | Compound (A) | Compound (B) |
| Z54 | A2 | (B6.2) |
| Z55 | A2 | (B6.3) |
| Z56 | A2 | (B6.4) |
| Z57 | A2 | (B7.4) |
| Z58 | A2 | (B7.5) |
| Z59 | A2 | (B8.1) |
| Z60 | A2 | (B8.5) |
| Z61 | A2 | (B9.10) |
| Z62 | A2 | (B 11.5) |
| Z63 | A2 | (B 11.6) |
| Z64 | A2 | (B 11.8) |
Table 2.3: Particularly preferred binary compositions comprising (A3)
| Binary composition | Compound (A) | Compound (B) | |
| Z65 | A3 | (Bl.7) |
| Z66 | A3 | (B1.8) |
| Z67 | A3 | (B1.14) |
| Z68 | A3 | (B2.3) |
| Z69 | A3 | (B2.18) |
| Z70 | A3 | (B2.24) |
| Z71 | A3 | (B2.25) |
| Z72 | A3 | (B2.26) |
| Z73 | A3 | (B2.28) |
| Z74 | A3 | (B2.31) |
| Z75 | A3 | (B2.34) |
| Z76 | A3 | (B2.37) |
| Z77 | A3 | (B2.68) |
| Z78 | A3 | (B2.69) |
| Z79 | A3 | (B2.72) |
| Z80 | A3 | (B4.18) |
| Z81 | A3 | (B4.25) |
| Z82 | A3 | (B5.7) |
| Z83 | A3 | (B5.23) |
| Z84 | A3 | (B5.31) |
| Z85 | A3 | (B5.38) |
| Z86 | A3 | (B6.2) |
| Z87 | A3 | (B6.3) |
| ZS8 | A3 | (B6.4) |
| Z89 | A3 | (B7.4) |
| Z90 | A3 | (B7.5) |
| Z91 | A3 | (B8.1) |
| Z92 | A3 | (B8.5) |
| Z93 | A3 | (B9.10) |
| Z94 | A3 | (B11.5) |
| Z95 | A3 | (B11.6) |
| Z96 | A3 | (B 11.8) |
Table 2.4; Partïcularly preferred binary compositions comprising (A4)
| Binary composition | Compound (A) | Compound (B) |
| Z97 | A4 | (B1.7) |
| Z98 | A4 | (B 1.8) |
| Z99 | A4 | (B 1.14) |
| ZI 00 | A4 | (B2.3) |
| Z101 | A4 | (B2.18) |
| Z102 | A4 | (B2.24) |
| Z103 | A4 | (B2.25) |
| Z104 | A4 | (B2.26) |
| Z105 | A4 | (B2.28) |
| Z106 | A4 | (B2.31) |
| ZI 07 | A4 | (B2.34) |
| Z108 | A4 | (B2.37) |
| ZI 09 | A4 | (B2.68) |
| ZI 10 | A4 | (B2.69) |
| ZI 11 | A4 | (B2.72) |
| Z112 | A4 | (B4.18) |
| Z113 | A4 | (B4.25) |
| ZI 14 | A4 | (B5.7) |
| Z115 | A4 | (B5.23) |
| Z116 | A4 | (B5.31) |
| ΖΓ17 | A4 | (B5.38) |
| Z118 | A4 | (B6.2) |
| Z119 | A4 | (B6.3) |
| ZI 20 | A4 | (B6.4) |
| Z121 | A4 | (B7.4) |
| Z122 | A4 | (B7.5) |
| Z123 | A4 | (B8.1) |
| ZI 24 | A4 | (B8.5) |
| Z125 | A4 | (B9.10) |
| Z126 | A4 | (B11.5) |
| Z127 | A4 | (B 11.6) |
| ZI 28 | A4 | (Bll.8) |
Table 2.5: Particularly preferred binary compositions comprising (A5)
| Binary composition | Compound (A) | Compound (B) |
| ZI 29 | A5 | (B1.7) |
| Z130 | A5 | (B1.8) |
| Z131 | A5 | (B 1.14) |
| ZI 32 | A5 | (B2.3) |
| Z133 | A5 | (B2.18) |
| Z134 | A5 | (B2.24) |
| ZI 35 | A5 | (B2.25) |
| Z136 | A5 | (B2.26) |
| Z137 | A5 | (B2.28) |
| Z138 | A5 | (B2.31) |
| Z139 | A5 | (B2.34) |
| ZI 40 | A5 | (B2.37) |
| Z141 | A5 | (B2.68) |
| Z142 | A5 | (B2.69) |
| Z143 | A5 | (B2.72) |
| Z144 | A5 | (B4.18) |
| Z145 | A5 | (B4.25) |
| Z146 | A5 | (B5.7) |
| Z147 | A5 | (B5.23) |
| Z148 | A5 | (B5.31) |
| Z149 | A5 | (B5.38) |
| Z150 | A5 | (B6.2) |
| Z151 | A5 | (B6.3) |
| Z152 | A5 | (B6.4) |
| Z153 | A5 | (B7.4) |
| Z154 | A5 | (B7.5) |
| Z155 | A5 | (B8.1) |
| Z156 | A5 | (B8.5) |
| Z157 | A5 | (B9.10) |
| Z158 | A5 | (B11.5) |
| Z159 | A5 | (B 11.6) |
| ZI 60 | A5 | (B11.8) |
Table 2.6: Particularly preferred binary compositions comprising (A6)
| Binary composition | Compound (A) | Compound (B) |
| ZI 61 | A6 | (B1.7) |
| ZI 62 | A6 | (B1.8) |
| Z163 | A6 | (B1.14) |
| Z164 | A6 | (B2.3) |
| Z165 | A6 | (B2.18) |
| Z166 | A6 | (B2.24) |
| Z167 | A6 | (B2.25) |
| Z168 | A6 | (B2.26) |
| Z169 | A6 | (B2.28) |
| ZI 70 | A6 | (B2.31) |
| Z171 | A6 | (B2.34) |
| Z172 | A6 | (B2.37) |
| ZI 73 | A6 | (B2.68) |
| ZI 74 | A6 | (B2.69) |
| Z175 | A6 | (B2.72) |
| Z176 | A6 | (B4.18) |
| Z177 | A6 | (B4.25) |
| ZI 78 | A6 | (B5.7) |
| ZI 79 | A6 | (B5.23) |
| ZI 80 | A6 | (B5.31) |
| ZI 81 | A6 | (B5.38) |
| Z182 | A6 | (B6.2) |
| Z183 | A6 | (B6.3) |
| Z184 | A6 | (B6.4) |
| ZI 85 | A6 | (B7.4) |
| Z186 | A6 | (B7.5) |
| ZI 87 | A6 | (B8.1) |
| Z188 | A6 | (B8.5) |
| Z189 | A6 | (B9.10) |
| Z190 | A6 | (B 11.5) |
| Z191 | A6 | (B 11.6) |
| Z192 | A6 | (B11.8) |
Table 2.7: Particularly preferred binary compositions comprising (A7)
| Binary composition | Compound (A) | Compound (B) |
| ZI 93 | A7 | (B1.7) |
| Z194 | A7 | (B1.8) |
| Z195 | A7 | (B1.14) |
| Z196 | A7 | (B2.3) |
| Z197 | A7 | (B2.18) |
| ZI 98 | A7 | (B2.24) |
| ZI 99 | A7 | (B2.25) |
| Z200 | A7 | (B2.26) |
| Z201 | A7 | (B2.28) |
| Z202 | A7 | (B2.31) |
| Z203 | A7 | (B2.34) |
| Z204 | A7 | (B2.37) |
| Z205 | A7 | (B2.68) |
| Z206 | A7 | (B2.69) |
| Z207 | A7 | (B2.72) |
| Z208 | A7 | (B4.18) |
| Z209 | A7 | (B4.25) |
| Z210 | A7 | (B5.7) |
| Z211 | A7 | (B5.23) |
| Z212 | A7 | (B5.31) |
| Z213 | A7 | (B5.38) |
| Z214 | A7 | (B6.2) |
| Z215 | A7 | (B6.3) |
| Z216 | A7 | (B6.4) |
| Z217 | A7 | (B7.4) |
| Z218 | A7 | (B7.5) |
| Z219 | A7 | (B8.1) |
| Z220 | A7 | (B8.5) |
| Z221 | A7 | (B9.10) |
| Z222 | A7 | (B 11.5) |
| Z223 | A7 | (B11.6) |
| Z224 | A7 | (B11.8) |
Table 2.8: Particularly preferred binary compositions comprising (A8)
| Binary composition | Compound (A) | Compound (B) |
| Z225 | A8 | (B1.7) |
| Z226 | A8 | (B 1.8) |
| Z227 | A8 | (B1.14) |
| Z228 | A8 | (B2.3) |
| Z229 | A8 | (B2.18) |
| Z230 | A8 | (B2.24) |
| Z231 | A8 | (B2.25) |
| Z232 | A8 | (B2.26) |
| Z233 | A8 | (B2.28) |
| Z234 | A8 | (B2.31) |
| Z235 | A8 | (B2.34) |
| Z236 | A8 | (B2.37) |
| Z237 | A8 | (B2.68) |
| Z238 | A8 | (B2.69) |
| Z239 | A8 | (B2.72) |
| Z240 | AS | (B4.18) |
| Z241 | A8 | (B4.25) |
| Z242 | A8 | (B5.7) |
| Z243 | A8 | (B5.23) |
| Z244 | A8 | (B5.31) |
| Z245 | A8 | (B5.38) |
| Z246 | A8 | (B6.2) |
| Z247 | A8 | (B6.3) |
| Z248 | A8 | (B6.4) |
| Z249 | A8 | (B7.4) |
| Z250 | A8 | (B7.5) |
| Z251 | A8 | (B8.I) |
| Z252 | A8 | (B8.5) |
| Z253 | A8 | (B9.10) |
| Z254 | A8 | (B11.5) |
| Z255 | A8 | (B11.6) |
| Z256 | A8 | (B 11.8) |
Table 2.9: Further particularly preferred binary compositions comprising (Al)
| Binary composition | Compound (A) | Compound (B) |
| Z257 | Al | (B3.1) |
| Binary composition | Compound (A) | Compound (B) |
| Z258 | Al | (B2.58) |
| Z259 | Al | (B4.22) |
Furthermore, the combinations of the invention can be used together with other active ingrédients such as the active ingrédients mentioned (herbicides, fongicides, insecticides, acaricides etc.) and/or plant growth regulators or auxilîaries from the group of additives customary in crop protection, such as adjuvants and 5 formulation aids. The combination of the active crop protection ingrédients comprising the active ingrédients (A) and (B) and optionally further active ingrédients are referred to hère as “herbicide combination” for short. Their use forms such as formulations or tankmixes are herbicidal products (compositions).
The invention therefore also provides the herbicidal products comprising the active ingrédient 10 combinations of the invention with additives customary in crop protection, such as adjuvants and formulation aids, and optionally further active crop protection ingrédients.
The invention also provides for the use of, or the application method using, the active ingrédient combinations of the invention as herbicides and plant growth regulators, preferably as herbicides and plant growth regulators having a synergistically active content of the respective active ingrédient combination 15 présent.
The application rates of the herbicides (B) are known in principle and are general! y in the range of 0.01 to 4000 g a.i./ha, preferably în the range of 0.02 to 2000 g a.i./ha, especially 1 to 2000 g a.i./ha. For the active ingrédient pelargonic acid (B5.38) from group (B5), the application rate is in the range of 1 to 100 000 g a.i./ha.
In the mixtures of the invention, in the context of the application rates mentioned, required application rates of the respective active ingrédient are generally lower compared to individual application.
For the active ingrédients from group (Bl), the application rate is preferably in the range of 5 to 250 g a.i./ha, especially in the range of 5 to 150 g/ha and most preferably in the range of 5 to 60 g a.i./ha.
For the active ingrédients from group (B2), the application rate is preferably in the range of 1 to 4000 g a.i./ha, especially in the range of 1 to 2000 g a.i./ha and most preferably in the range of 1 to 400 g a.i./ha.
For the active ingrédient from group (B3), the application rate is preferably in the range of 10 to 1000 g a.i./ha, especially in the range of 10 to 500 g a.i./ha and most preferably in the range of 10 to 300 g a.i./ha.
M For the active ingrédient from group (B4), the application rate îs preferably in the range of 1 to 7ÜÜ g a.i./ha, especially in the range of 1 to 400 g a.i./ha and most preferably in the range of 1 to 200 g a.i./ha.
For the active ingrédient from group (B5), excluding peïargonic acid (B5.38), the application rate is preferably in the range of 1 to 2400 g a.i./ha, especially in the range of 1 to 1200 g a.î./ha and most 5 preferably in the range of 1 to 400 g a.i./ha. For peïargonic acid (B5.38), the application rate is preferably 1 to 100 000 g a.i./ha, more preferably 1 to 40 000 g a.i./ha and especially in the range from 1 to 30 000 g a.i./ha.
For the active ingrédient from group (B6), the application rate is preferably in the range of 10 to 1000 g a.î./ha, especially in the range of 10 to 600 g a.i./ha.
For the active ingrédient from group (B7), the application rate is preferably in the range of 20 to 3500 g a.i./ha, especially in the range of 20 to 2500 g a.i./ha and most preferably in the range of 20 to 2000 g a.i./ha.
For the active ingrédient from group (BS), the application rate is preferably in the range of 5 to 1500 g a.i./ha, especially in the range of 5 to 1000 g a.i./ha and most preferably in the range of 5 to 900 g a.i./ha.
For the active ingrédient from group (B9), the application rate is preferably in the range of 2 to 2000 g a.i./ha, especially in the range of 2 to 1000 g a.i./ha, more preferably in the range of 2 to 200 g a.i./ha and most preferably in the range of 2 to 50 g a.i./ha.
For the active ingrédient from group (B10), the application rate is preferably in the range of 20 to 3500 g a.i./ha, especially in the range of 20 to 2000 g a.î./ha.
For the active ingrédient from group (Bl 1), the application rate is preferably in the range of 25 to 3000 g a.i./ha, especially in the range of 25 to 2500 g a.i./ha and most preferably in the range of 25 to 2000 g a.i./ha.
The ratios of (A);(B) based on weight, depending on the effective application rates, are generalîy in the 25 range of 1:100 000 to 2000:1, preferably 1:40 000 to 750:1, especially in the range of 1:15 000 to 500:1 and even further preferably in the range of 1:300 to 400:1.
For the active ingrédients from groups (Bl) to (Bll), the preferred weight ratios (A):(B) are as follows:
(A):(B1) preferably in the range of 30:1 to 1:30, especially of 15:1 to 1:15;
(A):(B2) preferably in the range of 400:1 to 1:400, especially of 200:1 to 1:200;
(A):(B3) preferably in the range of 30:1 to 1:30, especially of 15:1 to 1:15;
(A):(B4) preferably in the range of 300:1 to 1:300, especially of 150:1 to 1:150;
(A):(B5) preferably in the range of 400:1 to 1:300, especially of 300:1 to 1:150;
(A):(B6) preferably in the range of 60:1 to 1:60, especially of 30:1 to 1:30;
(A):(B7) preferably in the range of 10:1 to 1:200, especially of 1:1 to 1:100;
(A):(B8) preferably in the range of 30:1 to 1:300, especially of 10:1 to 1:80;
(A):(B9) preferably in the range of 80:1 to 1:200, especially of 40:1 to 1:100;
(A):(B10) preferably in the range of 10:1 to 1:300, especially of 3:1 to 1:150;
(A):(B11) preferably in the range of 30:1 to 1:300, especially of 15:1 to 1:150.
The herbicidal compositions of the invention can also be combined with further herbicides and plant growth regulators, for example to supplément the activity spectrum. Combination partners usable for the compounds according to the invention in mixed formulations or in a tankmix are, for example, known active ingrédients based on inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutamine synthetase, phydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem 1, pholosystem II, protoporphyrinogen oxidase, as known, for example, from Weed Research 26 (1986) 441-445 or “The Pesticide Manuaî”, 14th édition, The Britîsh Crop Protection Council and the Royal Soc. ofChemistry, 2006, the corresponding “e-Pesticide Manual Version 4 (2006)”, and literature cited therein, Further trade names and “common names” are listed in the “Compendium of Pesticide Common Names” (available on the Internet under http://www.alanwood.net/pesticidcs).
Examples of known herbicides which can be combined with the compounds of the invention include the active ingrédients which follow (N.B.: the compounds are designated either by the common naine according to the International Organization for Standardization (ISO) or by the Chemical name, in some cases together with a standard code number) and always encompass ail use forms, such as acids, salts, esters and isomers, such as stereoisomers and optical isomers. The list includes one and in some cases also more than one application form:
2,4-D, acetochlor, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, alloxydim, alloxydim-sodium, ametryn, amicarbazone, amidosulfuron, amitrole, amlofos, asulam, atrazine, azafenidm, azimsulfuron, beflubutamid, beiiazolin, benazolin-ethyl, benfuresate, bensulfuron-methyl, bentazone, benzfendizone, benzobicyclon, benzofenap, bifenox, bilanafos, bispyribac-sodium, bromacil, bromobutide, bromofenoxim, bromoxynil, butachlor, butafenacil, butenachlor, butralin, butroxydim, butyiate, cafenstrole, carbetamide, carie ntrazo ne-ethyl, chlomethoxyfen, chloridazon, ch lorimuron-ethyl, chloniitrofen, chlorotoluron, chlorsulfuron, cinidon-ethyl, cinmethylin, cinosulfuron, clefoxydim, clethodim, clodinafop-propargyl, clomazone, clomeprop, clopyralid, cloransulam-methyl, eu my luron, cyanazine, cyclosu Ifamuron, cycloxydiin, cyhalofop-butyl, desmedipham, dîcamba, dîchlobenîl, dichlorprop, dichlorprop-P, diclofop-methyl, diclosulam, difenzoquat, diflufenican, diflufenzopyr, dikegulac-sodium, dimefuron, dîmepiperate, dimethachlor, dimethametryn, dimethenamid, triaziflam, diquat-dibromide, dithiopyr, diuron, dymron, EPTC, esprocarb, ethalfluralin, ethametsulfuron-methyl, ethoxyfen, ethoxysulfuron, etobenzanid, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fentrazamide, flampropM-isopropyi, flamprop-M-melhyl, flazasulfuron, florasulam, fluazifop, fluazifop-butyl, fluazifop-butyl, fluazolate, flucarbazone-sodîum, flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flumetsulam, flumiclorac-pentyl, flumioxazin, fluometuron, fluorochloridone, fluoro glyco feu-ethyl, flupoxam, flupyrsulfuron-methyl-sodium, fluridone, fluroxypyr, fluroxypyr-butoxypropyl, fluroxypyr-meptyl, flurprimidol, flurtamone, fluthiacet-methyl, fomesafen, foramsulfuron, glufosinate, glufosinateammonium, glyphosate, halosulfuron-methyl, haloxyfop, haloxyfop-ethoxyethyl, haloxyfop-methyl, haloxyfop-P-methyi, hexazinone, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, iinazosulfuron, indanofan, iodosulfuron-methyl-sodium, ioxynil, isoproturon, isouron, isoxaben, isoxachlortole, isoxaflutole, ketospiradox, lactofen, lenacil, lin mon, MCP A, mecoprop, mecoprop-P, mefenacet, mesosulfuron-methyl, mesotrione, metamifop, metamitron, metazachlor, methabenzthiazuron, methyklymron, metobromuron, metolachlor, metosulam, metoxuron, metribuzin, metsulfuron-methyl, molinate, monolinuron, naproanilide, napropamide, neburon, nicosulfuron, norflurazon, orbencarb, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat, pelargonic acid, pendimethalin, pendralin, pentoxazone, pethoxamid, phenmedipham, picloram, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron-methyl, profluazol, profoxydîm, prometryn, propachlor, propanil, propaquizafop, propisochlor, propoxycarbazone-sodium, propyzamide, prosu] focarb, prosulfuron, pyraclonil, pyraflufen-ethyl, pyrazolate, pyrazosulfuron-ethyl, pyrazoxyfen, pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriftalid, pyriminobac-methyl, pyrithiobac-sodium, quinclorac, quinmerac, quinoclamine, quizalofop-ethyl, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron, sethoxydim, simazine, simetryn, S-metolachlor, sulcotrione, sulfenîrazone, sulfometuronmethyl, sulfosate, sulfosulfuron, tebuthiuron, tepraloxydim, terbuthylazine, terbutryn, thenylchlor, thiazopyr, thifensulfuron-methyl, thiobencarb, tiocarbazil, tralkoxydim, triallate, triasulfuron, tribenuronmethyl, triciopyr, tridiphane, trifloxysulfuron, trifluralin, triflusulfuron-methyl, tritosulfuron, WL 110547, i.e. 5-phenoxy-l-[3-(trifluoromethyl)phenyl]-lH-tetrazole; HOK-201, HOK-202, UBH-509; D-489; LS • 82-556; KPP-300; NC-324; NC-330; KH-218; DPX-N8189; SC-0774; TH-547, DOWCO-535; DK-8910; V-53482; PP-600; MBH-001; KIH-9201; ET-751; KIH-6127; KIH-2023 and KIH5996.
If the respective common name encompasses more than one form of the active ingrédient, the naine preferably defines the commercially available form.
Each of the further active ingrédients mentioned (= active ingrédients (C*), (Cl*), (C2*) etc.) may then preferably be combined with one of the binary combinations according to the présent invention, according to the scheme (A)+(B)+(C*) or else according to the scheme (Α)+(Β)+(ΰ1*)+(02*) etc.
The stated amounts are application rates (g a.i./ha = grams of active substance per hectare) and hence also define the ratios in a co-formulation, a premix, a tankmix or a sequential application of the combined 10 active ingrédients.
The combinations can be applied both by the pre-emergence method and by the post-emerge nce method. This applies both to pre- and post-emergence with respect to the harmful plants and, in the case of sélective control of the harmful plants, to pre- or post-emergence of the crop plants. Mixed forms are also possible, for example control of the harmful plants at their pre- or post-emergence stage after emergence of the crop 15 plants.
The herbicide combinations of the invention may comprise further components, for example other active ingrédients against harmful organisms such as harmful plants, plant-damaging animais or plant-damaging fungi, în this case especially active ingrédients from the group of herbicides, fungicides, insecticides, 20 acaricides, nematicides, miticides and reiated substances.
Fungicidally active compounds that can be used in combination with the herbicide combinations of the invention are preferably standard commercial active ingrédients, for example (analogously to lhe herbicides, the compounds are generally named by their common names):
1) Ergosterol biosynthesis inhibitors, for example (1.001) cyproconazole, (1.002) difenoconazole, (1.003) 25 epoxiconazole, (1.004) fenhexamid, (1.005) fenpropidin, (1.006) fenpropimorph, (1.007) fenpyrazamine, (1.008) fluquinconazole, (1.009) flutriafol, (1.010) imazaiil, (1.011) imazalil sulfate, (1.012) ipconazole, (1.013) metconazole, (1.014) myclobutanil, (1.015) paclobutrazole, (1.016) prochloraz, (1.017) propiconazole, (1.018) prothioconazole, (1.019) pyrisoxazole, (1.020) spiroxamine, (1.021) tebuconazole, (1.022) tetraconazole, (1.023) triadimenol, (1.024) tridemorph, (1.025) triticonazole, (1.026) (1R,2S,5S)30 5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-l-(lH-l,2,4-triazol-l-ylmethyl)cyclopentanol, (1.027) (lS,2R,5R)-5-(4-chlorobenzyl)-2-(chloromelhyI)-2-methyl-l-(lH-l,2,4-triazol-lylmethyl)cyclopentanol, (1.028) (2R)-2-(l-chlorocyclopropyl)-4-[(lR)-2,2-dîchlorocyclopropyl]-l-(lH20567 l,2,4-triazol-l-yl)butan-2-ol, (1.029) (2R)-2-(l-chlorocyclopropyl)-4-[(lS)-2,2-dichlorocyclopropyl]-l(lH-l,2,4-iriazol-l-yi)butan-2-oÎ, (1.030) (2R)-2-[4-(4-chlorophenoxy)-2-(trifluoroiiiethyl)pbenyl]-l(lH-l,2,4-triazol-l-yl)propan-2-ol, (1.031) (2S)-2-(l-chlorocyclopropyl)-4-[(lR)-2,2dichlorocyclopropyl]-l-(lH-l,2,4-triazol-l-yl)butan-2-oI, (1.032) (2S)-2-(l-chlorocyclopropyl)-4-[(lS)2,2-dichiorocyclopropyl]-l-(lH-l,2,4-triazol-l-yl)butan-2-ol, (1.033) (2S)-2-[4-(4-chlorophenoxy)-2(trifluoromethyI)phenyl]-l-(lH-l,2,4-triazol-l-yl)propan-2-ol, (1.034) (R)-[3-(4-chloro-2-fluorophenyl)5-(2,4-difÎuorophenyl)-l,2-oxazol-4-yI](pyridin-3-yl)methanol, (1.035) (S)-[3-(4-chloro-2fluorophenyl)-5-(2,4-difluorophenyl)-l,2-oxazol-4-yl](pyridin-3-yl)methanol, (1.036) [3-(4-chloro-2fluorophenyl)-5-(2,4-difluorophenyl)-l,2-oxazol-4-yl](pyridin-3-yl)methanol, (1.037) l-({(2R,4S)-2-[2chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-l,3-dioxolan-2-yl}inethyl)-lH-l,2,4-triazole, (1.038) 1({(2SJ4S)-2-[2-chloro-4-(4-chIorophenoxy)pheiiy!]-4-metbyl-l,3-dioxolan-2-yl}iïiethyl)-lH-l,2,4triazole, (1.039) l-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-lH-l,2,4-triazoI-5-yl thiocyanate, (1.040) l-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2J4-difluorophenyl)oxiran-2-yl]methyl}-lHl,2,4-triazol-5-yl thiocyanate, (1.041) l-{(rel(2R,3S)-3-(2-chIorophenyl)-2-(2,4-difluorophenyl)oxiran2-yl]methyl}-lH-l,2,4-triazol-5-yl thiocyanate, (1.042) 2-[(2R,4R,5R)-l-(2,4-dichloiophenyl)~5hydroxy-2,6J6-trimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4-triazole-3-tliioneJ (1.043) 2-[(2R,4R,5S)-l(2,4-dichloiOphenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4-triazole-3-thione, (1.044) 2-[(2R,4S,5R)-l-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yi]-2,4-dihydro-3Hl,2,4-triazoJe-3-thione, (1.045) 2-[(2R,4S,5S)-l-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan4-yl]-2,4-dihydro-3H-lf2,4-triazo!e-3-thione, (1.046) 2-[(2S,4R,5R)-l-(2,4-dichlorophenyl)-5-hydroxy2)6)6-trimethylbeptan-4-yl]-2,4-dihydro-3H-l,2,4-triazole-3-thione, (1.047) 2-[(2S,4R,5S)-l-(2,4dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4-triazole-3-thione, (1.048) 2-[(2S,4S,5R)-l-(2J4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylbeptan-4-yl]-2,4-dihydro-3H-l,2,4triazole-3-thione, (1.049) 2-[(2S,4S,5S)-l-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimetliyllieptati-4-yl]
2,4-dihydro-3H-l,2,4-tnazole-3-thione, (1.050)
2-[l-(2,4-dichlorophenyl)-5-hydroxy-2,6,6tnmethylheptan-4-yl]-2,4-dihydro-3H-l,2,4-triazoie-3-thione, dichlorophenoxy)phenyl]-l-(lH-l,2,4-triazol-l-yl)propan-2-ol, chlorophenoxyjphenylj-l-tlH-ljZA-triazol-l-yljbutan-Z-ol, (trifluoromcthyl)phenyl]-l-(lH-l,2,4-triazol-l-yl)butan-2-ol, (trifluoromethyl)phenyl]-l-(lH-l,2,4-triazol-l-yl)pentan-2-ol, (trifluoromethyl)phenyl]-l-(lH-l,2,4-triazol-l-yl)piOpan-2-ol, (1.051) 2-[2-chloro-4-(2,4(1.052) 2-[2-chloro-4-(4(1.053) (1.054) (1.055)
2-[4-(4-chlorophenoxy)-22-[4-(4-chlorophenoxy)-22- [4-(4-chlorophe noxy )-2(1.056) 2-{[3-(2-chlorophenyl)-2-(2,4difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-l}2,4-triazole-3-thione} (1.057) 2-{[rel(2R,3R)-3(2-chIoropheny 1)-2-(2,4-difluorophenyI)oxiran-2-yl]methyl}-2,4-dihydro-3H-l, 2,4-triazole-3-thione, (1.058) 2-{[rel(2R,3S)-3-(2-chloiOpbenyl)-2-(2,4-difluorophenyI)oxiran-2-yl]methyl}-2,4-dihydro-3Hl,2,4-triazole-3-thione, (1.059) 5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-l-(lH-l,2,4-triazol-lylmethyl)cyclopentanol, (1.060) 5-(allylsulfanyl)-l-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyI)oxiran2-y[]methyl}-lH-l,2,4-triazole, (1.061) 5-(allylsulfanyl)-l-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,420567 difltiorophenyl)oxiran-2-yl]methyl}-lH-l,2,4-triazole, (1.062) 5-(allylsulfanyl)-l-{[rel(2R,3S)-3-(2chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-lH-l,2,4-triazole, (1.063) N'-(2,5-dimethyl-4{[3-(1,1,2,2-tetrafluoroethoxy)phenyl]suIfanyI}phenyl)-N-ethyl-N-methylimi do formamîde, (1.064) N'(2,5-dimethyl-4-{[3-(2,2,2-trifluoroetlioxy)phenyl]sulfatiyl}phenyl)-N-ethyl-N-methyIimidoformamide, 5 (1.065) N'-(2,5-dimethyl-4-{[3-(2,2,3,3-tetrafluoropropoxy)phenyl]sulfanyl}p[ienyl)-N-ethyl-Nmethylimidoformamide, (1.066) N'-(2,5-dimethyl-4-{[3-(pentafluoroethoxy)phenyl]sulfanyl}phenyl)-Nethyl-N-methylimidoformamide, (1.067) N'-(2,5-dimethyl-4-{3-[(l,1,2,2tetrafluoroethyljsuifanylJphenoxyjphenylj-N-ethyl-N-methylimidoformamide, (1.068) N'-(2,5-dimethyl4-{3-[(2,2,2-trifluoroethyl)sulfanyl]phenoxy}phenyl)~N-ethyl-N-methylimidoformamide, (1.069) N’10 (2,5-dimethyl-4-{3-[(2,2,3,3-tetrafluoropropyl)sulfanyl]phenoxy}phenyl)-N-ethyl-Nmethylimidoformamide, (1.070) N'-(2,5-dimethyl-4-{3-[(pentafiuoroethyl)sulfanyl]phenoxy}phenyl)-Nethyl-N-methylimidoformamide, (1.071) N'-^S-dimethyM-phenoxyphenyO-N-ethyl-Nmethylimidoformamide, (1.072) N'-(4-{[3-(difluoromethoxy)phenyl]sulfanyl}-2,5-dimethylphenyl)-Nethyl-N-methylimidoformamide, (1.073) N'-(4-{3-[(difluoromethyl)sulfanyl]pbenoxy}-2,515 dimethylphenyl)-N-ethyl-N-methylimidoformamide, (1.074) N'-[5-bromo-6-(2,3-dihydro-lH-inden-2yloxy)-2-methylpyridm-3-yl]-N-ethyl-N-methylimidoformamide, (1.075) N'-{4-[(4,5-dichloro-l,3thiazol-2-yl)oxy]-2,5-dimethyIphenyl}-N-ethyl-N-methylimidoformamide, (1.076) N'-{5-bromo-6[(lR)-l-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (1.077) N,-{5-bromo-6-[(lS)-l-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N20 methylimidoformamide, (1.078) N'-{5-bromo-6-[(cis-4-isopropylcyclohexyl)oxy]-2-methylpyridm-3yl}-N-ethyl-N-methylimidoformamide, (1.079) N'-{5-bromo-6-[(trans-4-isopropylcycIohexyl)oxyJ-2methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (1.080) N’-{5-bromo-6-[ 1-(3,5difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methyiimidoformamide, (1.081) mefentrifluconazole, (1.082) ipfentrifluconazole.
2) Inhibitors of the respiratory chain in complex I or II, for example (2.001) benzovindiflupyr, (2.002) bixafen, (2.003) boscalid, (2.004) carboxin, (2.005) fluopyram, (2.006) flutoianil, (2.007) fluxapyroxad, (2.008) furametpyr, (2.009) isofetamid, (2.010) isopyrazam (anti-epimeric enantiomer 1R,4S,9S), (2.011) isopyrazam (anti-epimeric enantiomer 1S,4R,9R), (2.012) isopyrazam (anti-epimeric racemate 1RS,4SR,9SR), (2.013) isopyrazam (mixture of the syn-epimeric racemate 1RS,4SR,9RS and the anti30 epimeric racemate 1RS,4SR,9SR), (2.014) isopyrazam (syn-epimeric enantiomer 1R,4S,9R), (2.015) isopyrazam (syn-epimeric enantiomer 1S,4R,9S), (2.016) isopyrazam (syn-epimeric racemate 1RS,4SR,9RS), (2.017) penflufen, (2.018) penthiopyrad, (2.019) pydiflumetofen, ¢2.020) pyraziflumid, (2.021) sedaxane, (2.022) l,3-dimethyl-N-(l,l,3-trimethyl-2,3-dihydro-lH-inden-4-yl)-lH-pyrazole-4carboxamîde, (2.023) l,3-dimethyl-N-[(3R)-l,l,3-trimethyl-2,3-dihydro-lH-inden-4-yl]-lH-pyrazole-435 carboxamîde, (2.024) l,3-dimethyl-N-[(3S)-l,l,3-trimethyl-2,3-dihydro-lH-inden-4-yl]-lH-pyrazole-4carboxamide, (2.025) l-methyl-3-(trifluoromethyl)-N-[2'-(trifluoromethyl)biphenyl-2-yl]-lH-pyrazole4-carboxamide, (2.026) 2-fluoro-6-(trifluoromethyl)-N-(l,l,3-trimethyl-2,3-dihydro-lH-inden-4 fe yl)benzamide, (2.027) 3-(difluoromethyl)-l-methyl-N-(l,l,3-trimethyl-2,3-dihydro-lH-inden-4-yl)-lHpyrazole-4-carboxamide, (2.028) 3-(difluoromethyl)-l-methyl-N-[(3R)-l,l,3-trimetliyl-2,3-dihydro-lHinden-4-yl]-lH-pyrazole~4-carboxamide, (2.029) 3-(diiluoromethyl)-l-methyl-N-[(3S)-l,l,3-tnmethyl2,3-dihydro-lH-inden-4-yl]-lH-pyrazole-4-carboxamide, (2.030) 3-(difluoromethyl)-N-(7-fluoro-l,l,35 trimethyl-2,3-dihydro-lH-inden-4-yl)-l-methyl-lH-pyrazole-4-carboxamide, (2.031) 3(difluoromethyl)-N-[(3R)-7-fluoro-l,l,3-trimethyl-2,3-dihydro-lH-inden-4-yl]-l-methyl-lH-pyrazole4-carboxamide, (2.032) 3-(difluoromethyl)-N-[(3S)-7-fluoro-i,l,3-Erimethyl-2,3-dihydro-lH-indeiv4yI]-l-methyl-lH-pyrazole-4-carboxamide, (2.033) 5,8-difluoro-N-[2-(2-fluoro-4-{[4(Îrifluoromethyl)pyridin-2-yl]oxy}phenyl)ethyl]quinazolin-4-ainine, (2.034) N-(2-cyclopentyl-510 fluorobenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-l-methyl-lH-pyrazole-4-carboxamide, (2.035) N-(2-teΓt-butyl-5-methylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-l-methyl·lHpyrazole-4-carboxamide, (2.036) N-(2-tert-butylbenzy])-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-lmethyl-lH-pyrazole-4-carboxamide, (2.037) N-(5-chloro-2-etliylbenzyl)-N-cyclopropyb3(difluoromethyl)-5-fluoro-l-methyl-lH-pyrazole-4-carboxamide, (2.038) N-(5-chloro-215 isopropylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-l-methyl-lH-pyrazole-4-carboxamide, (2.039) N-[(lR,4S)-9-(dichloromethylene)-l,2,3,4-tetrahydro-l,4-methanonaphthalen-5-yl]-3(difluoromethyl)-l-methyl-lH-pyrazole-4-carboxamide, (2.040) N-[(lS,4R)-9-(dichloromethylene)l,2,3,4’tetraliydro-l,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-l-metbyl-lH-pyrazole-4carboxamide, (2.041) N-[l-(2,4-dichlorophenyl)-l-methoxypropan-2-yl]-3-(difluoromethyl)-l-methyl20 lH-pyrazoie-4-carboxamide, (2.042) N-[2-chloro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3(difluoromethyl)-5-fluoro-l-methyl-lH-pyrazole-4-carboxamide, (2.043) N-[3-chloro-2-fluoro-6(trifluoromethyl)benzylj-N-cyciopropyl-3-(difluoromethyl)-5-fluoro-l-methyl-lH-pyrazole-4carboxamide, (2.044) N-[5-chloro-2-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluorometbyl)-5fl uoro-1-methyl-lH-pyrazoie-4-carboxamide, (2.045) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-l25 methyl-N-[5-methyl-2-(trifluoromethyl)benzyl]-lH-pyrazole-4-carboxamide, (2.046) N-cyclopropyl-3(difluoromethyl)-5-fluoro-N-(2-fluoro-6-isopropylbenzyl)-l-methyl-lH-pyrazole-4-carboxamide, (2.047) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropyl-5-melhylbenzyl)-l-methyl-lHpyrazole-4-carboxamide, (2.048) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-lmethyl-lH-pyrazole-4-carbothioamide, (2.049) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(230 isopropylbenzyl)-l-methyl-lH-pyrazole-4-carboxamide, (2.05Ü) N-cyclopropyl-3-(difluorometliyl)-5fluoro-N-(5-fluoro-2-isopropylbenzyl)-l-methyl-lH-pyrazoIe-4-carboxamide, (2.051) N-cyclopropyl-3(difluoromethyl)-N-(2-ethyl-4,5-dimethylbenzyl)-5-fluoro-l-methyl-lH-pyrazole-4-carboxamide, (2.052) N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-fluorobenzyl)-5-fluoro-l-methyl-lH-pyrazole-4carboxamide, (2.053) N-cyclopropyl-3-(difluoromethyi)-N-(2-ethyl-5-methylbenzyl)-5-fluoro-l-methyl35 lH-pyrazole-4-carboxamide, (2.Ü54) N-cyclopropyl-N-(2-cyciopropyl-5-fluorobenzyl)-3(difluoromethyl)-5-fluoro-l-methyl-lH-pyrazole-4-carboxamide, (2.055) N-cyclopropyl-N-(2cyclopropyl-5-methyibenzyl)-3-(difluoromethyl)-5-fluoro-l-methyl-lH-pyrazole-4-carboxamide, (2.056) N-cyclopropyl-N-(2-cyclopropylbenzyl)-3-(difiuoromethyl)-5-fluoro-l-methyl-lH-pyrazole-4carboxamide.
3) Respiratory chain inhibitors acting on complex III, for example (3.001) ametoctradin, (3.002) amisulbrom, (3.003) azoxystrobin, (3.004) coumethoxystrobin, (3.005) coumoxystrobin, (3.006) cyazofamîd, (3.007) dimoxystrobin, (3.008) enoxastrobin, (3.009) famoxadon, (3.010) fenamidon, (3.011) flufenoxystrobin, (3.012) fluoxastrobin, (3.013) kresoxim-methyl, (3.014) metominostrobin, (3.015) orysastrobin, (3.016) picoxystrobin, (3.017) pyraclostrobin, (3.018) pyrametostrobin, (3.019) pyraoxystrobin, (3.020) trifloxystrobin, (3.021) (2E)-2-{2-[({[(lE)-l-(3-{[(E)-l-fluoro-2- phenylvinyl]oxy}phenyl)ethylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamide, (3.022) (2E,3Z)-5-{[l-(4-chlorophenyl)-lH-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3enamide, (3.023) (2R)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide, (3.024) (2S)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide, (3.025) (3Sf6S,7R,8R)-8-benzyl-3-[({3-[(isobutyryloxy)methoxy]-4-methoxypyridin-2-yl}carbonyl)amino]-6methyl-4,9-dioxo-l,5-dioxonan-7-yl 2-methylpropanoate, (3.026) 2-{2-[(2,5dimethyîphenoxy)methyl]phenyl}-2-methoxy-N-meÎhylacetamide, (3.027) N-(3-ethyl-3,5,5trimethylcycIohexyl)-3-formamido-2-hydroxybenzamide, (3.028) (2E,3Z)-5-{[l-(4-chloro-2fluorophenyl)-lH-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide, (3.029) methyl {5-[3-(2,4-dimethylphenyl)-lH-pyrazol-l-yl]-2-methylbenzyl}carbainate.
4) Mitosis and cell division inhibitors, for example (4.001) carbendazim, (4.002) diethofencarb, (4.003) ethaboxam, (4.004) fluopicolid, (4.005) pencycuron, (4.006) thiabendazole, (4.007) thiophanate-methyl. (4.008) zoxamide, (4.009) 3-chloro-4-(2,6-difluorophenyl)-6-methyl·5-phenyIpyridazine, (4.010) 3chloro-5-(4-chlorophenyl)-4-(2,6-difluorophenyl)-6-methylpyridazine, (4.011) 3-chloro-5-(6- chloropyridin-3-yl)-6-me¢hyl·4-(2,4,6-trifluorophenyl)pyridazine, (4.012) 4-(2-bromo-4-fluorophenyl)N-(2,6-difluorophenyl)-l,3-dimethyl-lH-pyrazol-5-amine, (4.013) 4-(2-bromo-4-fluorophenyl)-N-(2bromo-6-fl uoropheny 1)-1,3-dimethy 1-1 H-pyrazol bromophenyl)-l,3-dimethyl-lH-pyrazoE5-amine, fluorophenyl)-l,3-dimethyl-lH-pyrazol-5-amine, chlorophenyl)-l,3-dimethyl-lH-pyrazol-5-amine, fluorophenyl)-l,3-dimethyl-lH-pyrazol-5-amine, difluoroplienyl)-l,3-dimethyi-lH-pyrazol-5-amine, fluorophenyl)-l,3-dimethyl-lH-pyrazol-5-amine, chlorophenyl)-l,3-dimethyl-lH-pyrazol-5-amine,
-amine, (4.014) 4-(2-bromo-4-fluorophenyl)-N-(2(4.015) 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6(4.016) 4-(2-bromo-4-fluorophenyl)-N-(2(4.017) 4-(2-bromo-4-fluorophenyl)-N-(2(4.018) 4-(2-chloro-4-fluorophenyl)-N-(2,6(4.019) 4-(2-chloro-4-fluorophenyl)-N-(2-chloro-6(4.020) 4-(2-chloro-4-fl uoropheny I)-N-(2(4.021) 4-(2-chloro-4-fluorophenyl)-N-(2fluorophenyl)-l,3-dimethyMH-pyrazol-5-amine, (4.022) 4-(4-chlorophenyl)-5-(2,6-difIuorophenyl)-3,6dimethylpyridazine, (4.023) N-(2-bromo-6-fluorophenyl)-4-(2-chloro-4-fluorophenyl)-!,3-dimethyl-lH35 pyrazol-5-amine, (4.024) N-(2-bromophenyl)-4-(2-chloro-4-fluorophenyl)-l,3-dimethyl-lH-pyrazol-520567
A amine, (4.025) N-(4-chloro-2,6-difluorophenyI)-4-(2-chloro-4-fluorophenyl)-l,3-dîmethyl-lH-pyrazol5-amine.
5) Compounds with multisite activity, for example (5.001) Bordeaux mixture, (5.002) captafol, (5.003) captan, (5.004) chlorthalonil, (5.ÜO5) copper hydroxide, (5.006) copper naphthenate, (5.007) copper oxide, 5 (5.008) copper oxychloride, (5.009) copper(2+) sulfate, (5.010) dithianon, (5.011) dodine, (5.012) folpet, (5.013) mancozeb, (5.014) maneb, (5.015) metiram, (5.016) zinc metiram, (5.017) copper oxine, (5.018) propineb, (5.019) sulfur and sulfur préparations including calcium polysulfide, (5.020) thiram, (5.021) zineb, (5.022) zîram, (5.023) 6-ethyl-5,7-dioxo-6,7-dihydro-5H-pyrrolo[3',4':5,6][l,4]dithiino[2,3c][l,2]thiazole-3-carbonitrile.
6) Compounds capable of triggering host defence, for example (6.001) acibenzolar-S-methyl, (6.002) isotianil, (6.003) probenazole, (6.004) tiadinîl.
7) Amino acid and/or protein biosynthesis inhibitors, for example (7.001) cyprodinil, (7.002) kasugamycin, (7.003) kasugamycin hydrochloride hydrate, (7.004) oxytétracycline, (7.005) pyrimethanil, (7.006) 3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolm-l-yl)quinoline.
8) ATP production inhibitors, for example (8.001) sîlthiofam.
9) Cell wall synthesis inhibitors, for example (9.001) benthiavalicarb, (9.002) dimethomorph, (9.003) flumorph, (9.004) iprovalicarb, (9.005) mandipropamid, (9.006) pyrimorph, (9.007) valifenalate, (9.008) (2E)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-l-(morpholin-4-yl)prop-2-en-l-one, (9.009) (2Z)-3(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-l-(morpholin-4-yl)prop-2-en-l-onc.
10) Lipid and membrane synthesis inhibitors, for example (10.001) propamocarb, (10.002) propamocarb hydrochloride, (10.003) tolclofos-methyl.
11) Melanin biosynthesis inhibitors, for example (11.001) tricyclazole, (11.002) 2,2,2-trifluoroethyl-{3methyM-[(4-methylbcnzoyl)amino]butan-2-yl}carbamate.
12) Nucleic acid synthesis inhibitors, for example (12.001) benalaxyl, (12.002) benalaxyl-M (kiralaxyl), 25 (12.003) metalaxyl, (12.004) inetalaxyl-M (mefenoxam).
13) Signal transduction inhibitors, for example (13.001) fludioxonil, (13.002) iprodione, (13.003) procymidone, (13.004) proquinazid, (13.005) quinoxyfen, (13.006) vinclozolin.
14) Compounds that can act as decouplers, for example (14.001) fluazinam, (14.002) meptyldinocap.
15) Further compounds, for example (15.001) abscisic acid, (15.002) benthiazole, (15.003) bethoxazin, 30 (15.004) capsimycin, (15.005) carvone, (15.006) chinomethionat, (15.007) cufraneb, (15.008) cyflufenamid, (15.009) cymoxanil, (15.Ü1Û) cyprosulfamide, (15.011) flutîanil, (15.012) fosetylaluminium, (15.013) fosetyl-calcium, (15.014) fosetyl-sodium, (15.015) methyl isothiocyanate, (15.016) metrafenon, (15.017) mildiomycin, (15.018) natamycin, (15.019) nickel dimethyldithiocarbamate, (15.020) nitrothai-isopropyl, (15.021) oxamocarb, (15.022) oxathiapiprolin, (15.023) oxyfenthiin, 5 (15.024) pentachlorophenol and salts, (15.025) phosphonîc acid and salts thereof, (15.026) propamocarbfosetylate, (15.027) pyriofenone (chlazafenone), (15.028) tebufloquin, (15.029) tecloftalam, (15.030) tolnifanide, (15.031) l-(4-{4-[(5R)-5-(2,6-difluorophenyl)-4,5-dihydro-l,2-oxazol-3-yl]-l,3-Lhiazol-2yl}piperidin-l-yl)-2-[5-methyl-3-(trifluoromethyl)-lH-pyrazol-l-yl]ethanone, (15.032) l-(4-{4-[(5S)-5(2,6-difluorophenyl)-4,5-dihydro-l,2-oxazol-3-yl]-l,3-thiazol-2-yl}piperidm-l-yl)-2-[5-methyl-310 (trifluoromethyl)-lH-pyrazol-l-yl]ethanone, (15.033) 2-(6-benzylpyridin-2-yl)quinazoline, (15.034) 2,6dimethyl-lH,5H-[l,4]dithiino[2,3-c:5,6-c']dipyrrole-l,3,5,7(2H,6H)-tetrone, (15.035) 2-(3,5bis(dîfluoromethyl)-lH-pyrazol-l--yl]-l-[4-(4-{5-[2-(prop-2-yn-l-yloxy)phenyl]-4,5-dihydro-l,2oxazol-3-yl}-l,3-thiazol-2-yl)piperidin-l-yl]ethanone, (15.036) 2-[3,5-bis(difluoromethyl)-lH-pyrazoll-yl]-l-[4-(4-{5-[2-chioro-6-(prop-2-yn-l-yloxy)phenyl]-4,5-dihydro-l,2-oxazol-3-yl}-l,3-thiazol-215 yl)piperjdin-l-yl]ethanone, (15.037)2-[3,5-bis(difluoromethyl)-lH-pyrazol-l-yl]-l-[4-(4-{5-[2-fluoro-6(prop-2-yn-l-yloxy)phenyl]-4,5-dihydro-l,2-oxazol-3-yl}-l,3-thiazol-2-yl)piperidin-l-yl]ethanone, (15.038) 2-[6-(3-fluoiO-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazoline, (15.039) 2-{(5R)-3-[2-(l{[3,5-bis(difluoromethyl)-lH-pyrazol-l-yl]acetyl}piperidin-4-yl)-l,3-thiazol-4-yl]-4,5-dihydro-l,2oxazol-5-yl}-3-chiorophenyl methanesulfonate, (15.040) 2-{(5S)-3-[2-(l-{[3,5-bis(difluoromethyl)-lH20 pyrazol-l-yl]acetyl}piperidin-4-yl)-l,3-thiazol-4-yl]-4,5-dihydro-l,2-oxazol-5-yl}-3-chlorophenyl methanesulfonate, (15.041) 2-{2-[(7,8-difluoro-2-methylquinolin-3-yl)oxy]-6-fluorophenyl}propan-2-ol, (15.042) 2-{2-fluoro-6-[(8-fluoro-2-methylquinolin-3-yl)oxy]phenyl}propan-2-ol, (15.043) 2-{3-[2-(l{[3J5-bis(difluoromethyl)-lH-pyrazol-l-yl]acetyl}piperidin-4-yl)-lï3-thîazol-4-yl]-4,5-dihydro-l,2oxazol-5-yl}-3-chlorophenyl methanesulfonate, (15.044) 2-{3-[2-(l-{[3,5-bis(difluoromethyl)-lH25 pyrazol-l-yl]acetyI}piperidin-4-yi)-l,3-thiazol-4-yl]-4,5-dihydro-l,2-oxazol-5-yl}phenyl methanesulfonate, (15.045) 2-phenylphenol and salts thereof, (15.046) 3-(4,4,5-trifluoro-3,3-dimethyl3,4-dihydroisoquinolin-l-yl)qumoline, (15.047) 3-(4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-lyl)quinoline, (15.048) 4-amino-5-fluoropyrimîdm-2-ol (tautomeric form: 4-amino-5-fluoropyrimidin2(lH)-one), (15.049) 4-oxo-4-[(2-phenylethyl)amino]butyric acid, (15.050) 5-amino-l,3,4-thiadîazole-230 thiol, (15.051) 5-chloro-N'-phenyl-N'-(prop-2-yn-l-yl)thiophene 2-sulfonohydrazide, (15.052) 5-fluoro2-[(4-fluorobenzyl)oxy]pyrimidin-4-amine, (15.053) 5-f!uoro-2-[(4-methylbenzyl)oxy]pyrimidm-4amine, (15.054) 9-fluoro-2,2-dimethyl-5-(quinolin-3-yl)-2,3-dibydro-l,4-benzoxazepine, (15.055) but-3yn-l-yl {6-[({[(Z)-(l-methyl-lH-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2yl}carbamate, (15.056) ethyl (2Z)-3-amino-2-cyano-3-phenylacrylate, (15.057) phenazine-l-carboxylic 35 acid, (15.058) propyl 3,4,5-trihydroxybenzoate, (15.059) quinolin-8-ol, (15.060) quinolin-8-ol sulfate (2:1), (15.061) tert-butyl {6-[({[(l-methyl-lH-tetrazol-520567
B yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl)carbamate, (15.062) 5-fluoro-4-iniino-3-methyl1 )sulfonyl]-3,4-dihydropyrimidin-2(lH)-one.
Preferred fongicides are selected from the group consisting of benalaxyl, bitertano], bromuconazole, captafol, carbendazim, carpropamid, cyazofamid, cyproconazole, diethofencarb, edifenphos, 5 fenpropimorph, fentine, fluquinconazole, fosetyl, fluoroimide, folpet, iminoctadine, iprodionem, iprovalicarb, kasugamycin, maneb, nabam, pencycuron, prochloraz, propamocarb, propineb, pyrimethanil, spiroxamine, quintozene, tebuconazole, tolyliluanid, triadimefon, triadimenol, trifioxystrobin, zineb.
Insecticidal, acaricidal, nematicidal, miticidal and related active ingrédients are, for example (analogously 10 to the herbicides and fongicides, the compounds are, if possible, referred to by their common names):
(1) Acetylcholinesterase (AChE) inhibitors, preferably carbamates selected from alanycarb, aldicarb, bendiocarb, benforacarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, forathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thîodicarb, tliiofanox, triazamate, trimethacarb, XMC and xylylcarb; or organophosphates 15 selected from acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos/DDVP, dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, fosthîazate, heptenophos, imicyafos, isofenphos, isopropyl O-(methoxyaminothiophosphoryl) salicylate, isoxathion, malathion, mecarbam, 20 methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion-methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxîm, pirimiphos-methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, triciorfon and vamidothion.
(2) GABA-gatcd chloride channel blockers, preferably cyclodiene-organochlorines selected from 25 chlordane and endosulfan, or phenylpyrazoles (fiproles) selected from ethiprole and fipronil.
(3) Sodium channel modulators, preferably pyrethroids selected from acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S-cyclopentenyl isomer, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cylialothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, 30 cyphenothrin [(IR)-trans isomer], deltamethrin, empenthrîn [(EZ)-(IR) isomer], esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, îmiprothrin, kadethrin, momfluorothrin, permethrin, phenothrin [(IR)-trans isomer], prallethrin, pyrethrins (pyrethrum), resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [(1 R) isomer], tralomethrin and transfluthrin or DDT or methoxychlor.
B (4) Nicotinic acétylcholine receptor (nAChR) compétitive modulators, preferably neonicotinoids selected from acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam, or nicotine, or sulfoximines selected from sulfoxaflor, or butenolides selected from flupyradifurone.
(5) Nicotinic acétylcholine receptor (nAChR) allosteric modulators, preferably spinosyns selected from 5 spînetoram and spinosad.
(6) Glutamate-gated chloride channel (GluCl) allosteric modulators, preferably avermectins/milbemycins selected from abamectîn, emamectin benzoate, lepimectin and milbemectin.
(7) Juvénile hormone mimics, preferably juvénile hormone analogues selected from hydroprene, kînoprene and methoprene, or fenoxycarb or pyriproxyfen.
(8) Miscellaneous non-specific (multi-site) inhibitors, preferably alkyl halides selected from methyl bromide and other alkyl halides; or chloropicrin or sulfuryl fluoride or borax or tartar emetic or methyl isocyanate generators selected from diazomet and metam.
(9) Chordotonal organ TRPV channel modulators selected from pymetrozîne and pyrifluquinazon.
(10) Mite growth inhibitors selected from clofentezine, hexythiazox, diflovîdazin and etoxazoie, (11) Microbial disruptors of insect midgut membranes selected from Bacillus thuringiensis subspecies israelensis, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis, and B.t. plant proteins selected from CrylAb, CrylAc, CrylFa, CrylA.105, Cry2Ab, VIP3A, mCry3A, Cry3Ab, Cry3Bb and Cry34Abl/35Abl.
(12) Inhibitors of mitochondrial ATP synthase, preferably ATP disruptors selected from diafenthiuron, or organotin compounds selected from azocyclotin, cyhexatin and fenbutatin oxide, or propargite or tetradifon.
(13) Uncouplers of oxidative phosphorylation via disruption of the proton gradient, selected from chiorfenapyr, DNOC and sulfluramid.
(14) Nicotinic acétylcholine receptor channel blockers selected from bensultap, cartap hydrochioride, thiocyclam, and thiosultap-sodium.
(15) Inhibitors of chitin biosynthesis, type 0, selected from bistrifluron, chlorfluazuron, diflubenzuron, flucycioxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron and triflumuron.
(16) Inhibitors of chitin biosynthesis, type 1, selected from buprofezin.
(17) Moulting disruptors (especially in the case of Diptera) selected from cyromazine.
(18) Ecdysone receptor agonists selected from chromafenozide, halofenozide, methoxyfenozide and tebufenozide.
(19) Octopamine receptor agonists selected from amitraz.
(20) Mitochondrial compiex ΠΙ électron transport inhibitors selected from hydramethylnon, acequinocyl and fluacrypyrim.
(21) Mitochondrial compiex I électron transport inhibitors, preferably METI acaricides selected from fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad and tolfenpyrad, or rotenone (Denis).
(22) Voltage-dependent sodium channel blockers selected from indoxacarb and metaflumizone.
(23) Inhibitors of acetyl-CoA carboxylase, preferably te ironie and tetramic acid dérivatives selected from spirodiclofen, spiromesifen and spirotetramat.
(24) Mitochondrial compiex IV électron transport inhibitors, preferably phosphines selected from aluminium phosphide, calcium phosphide, phosphine and zinc phosphide, or cyanides selected from calcium cyanide, potassium cyanide and sodium cyanide.
(25) Mitochondrial compiex II électron transport inhibitors, preferably beta-keto nitrile dérivatives selected from eyenopyrafen and cyflumetofen, or carboxanilides selected from pyflubumide.
(28) Ryanodine receptor modulators, preferably diamides selected from chlorantraniliprole, cyantraniliprole and flubendiamide.
(29) Chordotoiial organ modulators (with undefined target structure) selected from flonicamid.
(30) Further active ingrédients selected from acynonapyr, afidopyropen, afoxolaner, azadirachtîn, benclothiaz, benzoximate, benzpyrimoxan, bifenazate, broflanilide, bromopropylate, chinomethionat, chloroprallethrîn, cryolite, cyclaniliprole, cycloxaprid, cyhalodiamide, dicloromezotiaz, dicofol, epsilon metofluthrin, epsilon momfluthrin, flometoquin, fluazaindolizine, fluensulfone, flufenerim, flufenoxystrobin, flufiprole, fluhexafon, fluopyram, flupyrimin, fluralaner, fluxametamide, fufenozide, guadipyr, heptafluthrin, imidaclothiz, iprodione, kappa bîfenthrin, kappa tefluthrin, lotilaner, meperfluthrin, oxazosulfyl, paichongding, pyridaly 1, pyrifluquinazon, pyriminostrobin, spirobudiclofen, spiropidion, tetramethylfluthrin, tetraniliprole, tetrachlorantraniliprole, tigolaner, tioxazafen, thiofluoximate, triflumezopyrim and iodomethane; additionally préparations based on Bacilliis firmus (I1582, BioNeem, Votivo), and the foliowing compounds: l-{2-fluoro-4-methyl-5-[(2,2,2trifIuoroethyl)suIfinyl]phenyl}-3-(trifIuoromethyl)-lH-l,2,4-triazole-5-amine (known from
WO2006/043635) (CAS 885026-50-6), {r-[(2E)-3-(4-chlorophenyl)prop-2-en-l-y)]-5fluorospiro[indole-3)4'-piperidine]-l(2H)-yl}(2-chloropyridin-4-yl)methanone (known from WO2003/106457) (CAS 637360-23-7), 2-chloro-N-[2-{l-[(2E)-3-(4-chlorophenyl)prop-2-en-lyl]piperidin-4-yl}-4-(trifluoromethyl)phenyl]isonicotinamide (known from WO2006/003494) (CAS 5 872999-66-1), 3-(4-cliloro-2,6-dimethylphenyl)-4-hydroxy-8-methoxy-l,8-diazaspiro[4.5]dec-3-en-2one (known from WO 2010052161) (CAS 1225292-17-0), 3-(4-chloro-2,6-dimetliylphenyl)-8-methoxy2-oxo-l,8-diazaspiro[4.5]dec-3-en-4-yl ethylcarbonate (known from EP 2647626) (CAS-1440516-42-6), 4-(but-2-yn-l-yioxy)-6-(3,5-dimethylpiperidin-l-yl)-5-fluoropyrimidine (known from W02004/099160) (CAS 792914-58-0), PF1364 (known from JP2010/018586) (CAS Reg.No. 1204776-60-2), (3E)-3-[l-[(610 chloro-3-pyridyl)methyl]-2-pyridylidene]-l,l,l-trifluoropropan-2-one (known from WO2013/144213) (CAS 1461743-15-6), N-[3-(benzylcarbamoyl)-4-chlorophenyl]-l-methyl-3-(pentafluoroethyl)-4(trifluoromethyl)-lH-pyrazole-5-carboxamide (known from WO2010/051926) (CAS 1226889-14-0), 5bromo-4-cbloro-N-[4-ch!oro-2-methyl-6-(methylcarbamoyl)phenyl]-2-(3-chloiO-2-pyridyl)pyrazole-3carboxamide (known from CN103232431) (CAS 1449220-44-3), 4-[5-(3,5-dichloropheny 1)-4,5-dihydro15 5-(trifluoromethyl)-3-isoxazolyl]-2-methy]-N-(cis-l-oxido-3-thietanyl)benzamide, 4-[5-(3,5dichlorophenyl)-4,5“dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(trans-l-oxido-3thietanyl)benzamide and 4-[(5S)-5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazo]yl]2-metbyl-N-(cis-l-oxido-3-thietanyl)benzamide (known from WO 2013/050317 Al) (CAS 1332628-837), N-[3-chloro-l-(3-pyridinyl)-lH-pyrazol-4-yl]-N-ethyl-3-[(3,3,320 trifluoropropyl)sulfinyl]propanamide, (+)-N-[3-chloro-l-(3-pyridinyl)-lH-pyrazol-4-yl]-N-elhyl-3[(3,3,3-trifluoropropyl)sulfinyl]propanamide and (-)-N-[3-chloro-l-(3-pyridinyI)-lH-pyrazol-4-yl]-Nethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]propanamide (known from WO 2013/162715 A2, WO 2013/162716 A2, US 2014/0213448 Al) (CAS 1477923-37-7), 5-[[(2E)-3-chloro-2-propen-l-yl]amino]1-[2,6-dicliloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-lH-pyrazole-3-carbonitrile (known from CN 101337937 A) (CAS 1105672-77-2), 3-bromo-N-[4-chloro-2-methyl-6[(methylamino)thioxomethyl]phenyl]-l-(3-chloro-2-pyridinyi)-lH-pyrazole-5-carboxamide (Liudaibenjiaxuanan, known from CN 103109816 A) (CAS 1232543-85-9); N-[4-chloro-2-[[(l,ldimethylethyl)amino]carbonyl]-6-methylphenyl]-l-(3-chloro-2-pyridinyl)-3-(fIuorometboxy)-lHp y razole-5-carboxamide (known from WO 2012/034403 Al) (CAS 1268277-22-0), N-[2-(5-amino-l,3,430 thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-l-(3-chloro-2-pyridinyl)-lH-py razole-5carboxamide (known from WO 2011/085575 Al) (CAS 1233882-22-8), 4-[3-[2,6-dichloiO-4-[(3,3dichloro-2-propen-l-yl)oxy]phenoxy]propoxy]-2-methoxy-6-(trifluoromethyl)pyrimidine (known from CN 101337940 A) (CAS 1108184-52-6); (2E)- and 2(Z)-2-[2-(4-cyanophenyl)-l-[3(trifluoromeÜiyl)piienyl]ethyiidene]-N-[4-(difluoromethoxy)phenyl]hydrazinecarboxamide (known from 35 CN 101715774 A) (CAS 1232543-85-9); cyclopropanecarboxylic acid 3-(2,2-dichloroetheny])-2,2dimethyl-4-(lH-benzimîdazol-2-yl)phenyi ester (known from CN 103524422 A) (CAS 1542271-46-4);
(4aS)-7-chloro-2,5-dihydro-2-[[(methoxycarbonyl)[420567
A [(trifluoromethy])thÎo]phenyl]amino]carbonyl]indeno[l,2-e][l,3,4]oxadiazine-4a(3H)-carboxylic acid methyl ester (known from CN 102391261 A) (CAS 1370358-69-2); 6-deoxy-3-O-ethyl-2,4-di-O-methyll-[N-[4-[l-[4-(l,l,2,2,2-pentafluoroethoxy)phenylJ-lH-l,2,4-triazol-3-yl]phenyl]carbamate]-a-Lmannopyranose (known from US 2014/0275503 Al) (CAS 1181213-14-8); 8-(2-cycIopropylmethoxy-45 trifluoromethylphenoxy)-3-(6-trifluoromethylpyridazin-3-yl)-3-azabicyclo[3.2.1]octane (CAS 125385056-4), (8-anti)-8-(2-cyclopropylmethoxy-4-trifluoromethylphenoxy)-3-(6-trifluoromethylpyridazÎn-3yl)-3-azabicyclo[3.2.1]octane (CAS 933798-27-7), (8-syn)-8-(2-cyclopropylmethoxy-4trifluoromethylphenoxy)-3-(6-trifluoromethylpyridazin-3-y1)-3-azabicyclo[3.2.1]octane (known from WO 2007040280 Al, WO 2007040282 Al) (CAS 934001-66-8), N-[3-chloro-l-(3-pyridinyl)-lH10 pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)thio]propanamide (known from WO 2015/058021 Al, WO 2015/058028 Al) (CAS 1477919-27-9) and N-[4-(amiiiothioxomethyl)-2-methyl-6[(methylamino)carbonyl]pheny]]-3-bromo-l-(3-chloro-2-pyridinyl)-lH-pyrazole-5-carboxamide (known from CN 103265527 A) (CAS 1452877-50-7), 5-(l,3-dioxan-2-yI)-4-[[4(tnfluoromethyl)phenyl]methoxy]pyrimidine (known from WO 2013/115391 Al) (CAS 1449021-97-9), 15 3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-l-methyl-l,8-diazaspiro[4.5]decane-2,4-dione (known from
WO 2014/187846 Al) (CAS 1638765-58-8), ethyl 3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-lmethyl-2-oxo-l,8-d!azaspiro[4.5]dec-3-en-4-ylcarboxylate (known from WO 2010/066780 Al, WO 2011151146 Al) (CAS 1229023-00-0), 4-[(5S)-5-(3,5-dichloro-4-fiuorophenyl)-4,5-dihydro-5(trifluoromethyl)-3-isoxazolyl]-N-[(4R)-2-ethyl-3-oxo-4-isoxazolidinyl]-2-methylbenzamide (known 20 from WO 2011/067272, WO2013/050302) (CAS 1309959-62-3).
Insecticides that can preferably be used together with the herbicides are, for example, as follows:
acetamiprid, acrinathrîn, aldicarb, amitraz, acinphos-methyl, cyfluthrin, carbaryl, cypermethrin, deltamethrîn, endosulfan, ethoprophos, fenamiphos, fenthion, fipronii, îmidacloprid, methamidophos, methiocarb, niclosamide, oxydemeton-methyl, prothîophos, silafluofen, thiacloprid, thiodicarb, 25 tralomethrin, triazophos, trichlorfon, triflumuron, terbufos, fonofos, phorate, chlorpyriphos, carbofuran, tefluthrin.
The active ingrédient combinations of the invention are suitable for control of a broad spectrum of weeds on uncultivatcd land, on pathways, on raîlway tracks, in industrial areas (industrial weed control) or in plantation crops, such as temporale, subtropical and tropical climates or geographies. Examples of 30 plantation crops are oil palms, nuts (e.g. almonds, hazelnuts, walnuts, macadamia), coconut, berries, rubber trees, citrus (e.g. oranges, lemons, mandarins), bananas, pineapples, cotton, sugarcane, tea, coffee, cacao and the like. They are likewise suitable for use in pomiculture (e.g. pomaceous fruits such as apples, pears, cherries, mangoes and kiwis) and viticulture. The compositions can also be used for préparation for seeding (burn-down, no-till or zero-till method) or for treatment after harvesting (chemical 35 fallow). The possible uses of the active ingrédient combinations also ex tend to weed control in tree crops,
B for example young Christmas tree crops or eucalyptus crops, in each case before planting or after planting (including over-top treatment).
The compositions can also be used to control unwanted plant growth in economically important crop 5 plants such as wheat (hard and soft wheat), maize, soya, sugarbeet, sugarcane, cotton, rice, beans (for example, bush beans and broad beans), flax, barley, oats, rye, triticale, potato and millet/sorghum, pastureland and areas of grass/lawn and plantation crops. Plantation crops are, inter alla, pomaceous fruit (apple, pear, quince), Ribes species (blackberry, raspberry), citrus, Prunus species (cherries, nectarines, almonds), nuts (walnut, pecan nut, hazelnut, cashew, macadamia), mango, cacao, coffee, grapevines (for 10 eating or for making wine), palms (such as oil palms, date palms, coconut palms), eucalyptus, kaki, persimmon, caoutchouc, pîneapple, banana, avocado, lychee, forest cultures (Eucalypteae, Piniaceae, Piceae, Meliaceae, etc.).
The active herbicidal ingrédient combinations of the invention, in the respective use fonns (= herbicidal products), hâve synergies with regard to herbicidal action and selectivity, and favourable action with 15 regard to the spectrum of weeds. They hâve excellent herbicidal efficacy against a broad spectrum of economically important monocotyledonous and dicotyledonous annual harmful plants. The active ingrédients also hâve good control over perennial harmful plants which are dîfficult to control and produce shoots from rhizomes, rootstocks or other perennial organs.
For application, the active ingrédient combinations can be deployed onto the plants (e.g. harmful plants 20 such as mono- or dicotyledonous weeds or unwanted crop plants), the seed (e.g. grains, seeds or végétative propagation organs such as tubers or parts of shoots having buds), or the area in which the plants grow (e.g. the growîng area).
The substances can be deployed prior to sowing (if appropriate also by incorporation into the soîl), prior to emergence or after emergence. Preference is given to use by the early post-seeding pre-emergence 25 method or by the post-emergence method in plantation crops against harmful plants that hâve not y et emerged or hâve already emerged. The application can also be integrated into weed management Systems with dividcd repeated applications (sequentials).
Spécifie examples of some représentatives of the mono- and dicotyledonous weed flora which can be controlled by the active ingrédient combinations accordîng to the invention are as follows, although the 30 énumération is not intended to impose a restriction to particular species.
Among the monocotyledonous weed species, for example, Aegilops, Agropyron, Agrostis, Aiopecurus, Apera, Avena, Brachicaria, Bromus, Cynodon, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Imperata, Ischaemum, Heteranthera, Imperata,
B Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum, Sphenoclea and Cyperus species are covered by the annual group.
In the case of dicotyledonous weed species, the spectrum of action extends to species such as, for example, Abutilon, Amaranthus, Ambrosia, Anoda, Anthémis, Aphanes, Artemisia, Atriplex, Beilîs, Bidens, 5 Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erodium, Erysimum, Euphorbia, Galeopsis, Galînsoga, Galium, Géranium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotaia, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapîs, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, 10 Veronica, Viola, Xanthium.
If the active ingrédient combinations of the invention are applied to the soil surface before germination, either the emergence of the weed seedlings is prevented completely or the weeds grow until they hâve reached the cotylédon stage, but then stop growing and ultimately die completely after three to four weeks hâve passed.
If the active ingrédients are applied post-emergence to the green parts of the plants, growth stops after the treatment, and the harmful plants remain at the growth stage at the time of application, or they die completely after a certain time, and so this éliminâtes compétition by the weeds, which is harmful to the crop plants, very early and in a sustained manner.
The herbicidal products of the invention are notable for a rapid onset and long duration of herbicidal 20 action. In general, the rainfastness of the active ingrédients in the combinations of the invention is favourable. A particular advantage is that the effective dosages of compounds (A) and (B) that are used in the combinations can be adjusted to such a low level that their soil action is optimally low. Therefore, the use thereof in sensitive crops îs not just enabled, but groundwater contamination is also virtually prevented. The inventive combination of active ingrédients allows the required application rate of the 25 active ingrédients to be reduced considerably.
The combined use of herbicides (A) and (B) achîeves performance properties extending beyond what was to be expected on account of the known properties of the indîvîdual herbicides for the combination thereof. For example, the herbicidal effects for a particular harmful plant species excced the expected value as can be estimated by standard methods, for example according to Colby or other extrapolation methods.
A synergistic effect exists whenever the effect, the herbicidal effect here, of the active ingrédient combination îs greater than the sum total of the effects of the active ingrédients applied individually. The expected activity for a gîven combination of two active ingrédients can be calculated according to S.R.
B Colby (“Calculating Synergistic and Antagonistic Responses of Herbicide Combinations”, Weeds 15 (1967), 20-22) (see below).
The synergistic effects therefore permit, for example, a réduction in the application rates of the individual active ingrédients, a higher efficacy at the same application rate, the control of species of harmful plants 5 which are as yet uncovered (gaps), elevated residual action, an extended period of efficacy, an elevated speed of action, an extension of the period of application and/or a réduction in the number of individual applications required and - as a resuit for the user - weed control Systems which are more advantageous economically and ecologically.
Even though the combinations of the invention hâve excellent herbicidal activity with respect to mono10 and dicotyledonous weeds, many economically important crop plants, depending on the structure of the respective active ingrédient combinations of the invention and the application rate thereof, are damaged only insignificantly, îf at alL Economically important crops here are, for example, dicotyledonous crops from the généra of Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or 15 monocotyledonous crops from the généra of Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum and Zea.
In addition, the compositions of the invention in some cases hâve outstanding growth-regulating properties in crop plants. They intervene in the plants’ owo metabolism with regulatory effect, and can thus be used for the controlled influencing of plant constituents and to facilitate harvesting, for example by triggering 20 desiccation and stunted growth. Furthermore, they are also suitable for the general control and inhibition of unwanted végétative growth without killing the plants in the process. Inhibition of végétative growth plays a major rôle for many mono- and dicotyledonous crops since this can reduce or completely prevent lodging.
Owing to their herbicidal and plant growth-regu la tory properties, the compositions can be used to control 25 harmful plants in known plant crops or in tolérant crop plants still to be developed, modified by conventional mutagenesis or modified by genetic engineering. In general, transgenic plants feature particular advantageous properties in addition to résistances to the compositions of the invention, for example résistances to plant diseases or the organisais that cause plant diseases such as certain insects, or microorganîsms such as fungi, bacteria or viruses. Other particular properties relate, for example, to the 30 harvested material with regard to quantity, quality, storability, composition and spécifie constituents. For instance, there are known transgenic plants with an elevated starch content or altered starch quality, or those with a different fatty acid composition in the harvested material. Other particular properties may be tolérance or résistance to abiotic stressors, for example heat, low températures, drought, salinity and ultraviolet radiation.
B The active ingrédient combinations of the invention can preferably be used as herbicides in crops of crop plants that are résistant, or hâve been made résistant by genetic engineering, to the phytotoxic effects of the herbicides.
Conv en trônai ways of producing novel plants which hâve modified properties in comparison to existing 5 plants consîst, for example, in traditional cultivation methods and the génération of mutants.
Aiternatively, novel plants with modified properties can be generated with the aid of recombinant methods (see, for example, EP-A-0221044, EP-A-0131624). For example, there hâve been descriptions in several cases of:
genetic modifications of crop plants for the purpose of modifying the starch synthesized in the plants (e.g. WO 92/11376, WO 92/14827,
WO 91/19806), transgenic crop plants which exhibit résistances to other herbicides, for example to sulfonylureas (EP-A-0257993, US-A-5013659), transgenic crop plants with the ability to produce
Bacîllus thuringiensis toxins (Bt toxins), which make the plants résistant to particular pests (EP-A-0142924, EP-A-0193259), transgenic crop plants with a modified fatty acid composition (WO 91/13972),
- genetically modified crop plants with novel constituents or secondary métabolites, for example novel phytoalexins, which bring about an increased disease résistance (EPA 309862, EPA0464461), genetically modified plants having reduced photo respiration, which hâve higher yields and higher stress tolérance (EPA 0305398),
- transgenic crop plants which produce pharmaceuticaliy or diagnostically important proteins (molecular pharmiog), transgenic crop plants which feature higher yields or better quality, transgenic crop plants which feature a combination, for example, of the abovementioned novel properties (gene stacking).
Numerous molecular biology techniques which can be used to produce novel transgenic plants with modified properties are known in principle; see, for example, I. Potrykus and G. Spangenberg (eds.) Gene Transfer to Plants, Springer Lab Manual (1995), Springer Verlag Berlin, Heidelberg, or Christou, Trends in Plant Science 1 (1996) 423-431.
For such recombinant manipulations, nucieic acid molécules which ailow mutagenesis or sequence 35 alteration by recombination of DNA sequences can be introduced into plasmids. With the aid of standard
100 methods, it is possible, for example, to undertake base exchanges, remove parts of sequences or add natural or synthetic sequences. For the connection of the DNA fragments to one another, it is possible to add adapters or linkers to the fragments; see, for example, Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd ed., Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY; or Winnacker Gene und Klone” [Genes and Clones], VCH Weinheim, 2nd édition, 1996.
For example, the génération of plant cells with a reduced activity of a gene product can be achieved by expressing at least one corresponding antisense RNA, a sense RNA for achieving a cosuppression effect, or by expressing at least one suitably constructed ribozyme which specifically cleaves transcripts of the abovementioned gene product.
To this end, it is firstly possible to use DNA molécules which encompass the enlire coding sequence of a gene product inclusive of any flanking sequences which may be présent, and also DNA molécules which only encompass portions of the coding sequence, in which case it is necessary for these portions to be long enough to hâve an antisense effect in the cells. It is also possible to use DNA sequences which hâve a high degree of homology to the coding sequences of a gene product, but are not completely identical to them.
When expressing nucleic acid molécules in plants, the protein synthesized may be localized in any desired compartment of the plant cell. However, to achieve localization in a particular compartment, it is possible, for example, to join the coding région to DNA sequences which ensure localization in a particular compartment. Such sequences are known to those skilled in the art (see, for exampie, Braun et al., EMBO J. i 1 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad. Sci. USA 85 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991), 95-106). The nucleic acid molécules can also be expressed in the organelles of the plant cells.
The transgenic plant cells can be regenerated by known techniques to give rise to entire plants. In principle, the transgenic plants may be plants of any desired plant species, i.e. not only monocotyledonous but also dicotyledonous plants. Obtainabîe in this way are transgenic plants having properties altered by overexpression, suppression or inhibition of homologous (= natural) genes or gene sequences or expression of heterologous (= foreign) genes or gene sequences.
The active ingrédient combinations of the invention can preferably be used in transgenic crops that are tolérant or hâve been rendered tolérant to the active ingrédients used.
The active ingrédient combinations of the invention can preferably also be used in transgenic crops which are résistant to growth regulators, for example dicamba, or to herbicides which inhibit essential plant enzymes, for exampie acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or
101 hydroxyphenylpyruvate dioxygenases (HPPD), or to herbicides from the group of the sulfonylureas, the glyphosates, glufosinates or benzoyhsoxazoles and analogous active mgredients.
The invention therefore also provides a method of cootrolling unwanted plant growth, optionally in crops of crop plants, preferably on uncultivated land or in plantation crops, characterized in that one or more herbicides of type (A) is/are applied with one or more herbicides of type (B) to the harmful plants, parts of plants or plant seeds (seed) or to the growing area.
The invention also provides for the use of the novel combinations of compounds (A)+(B) for control of harmful plants, optionally in crops of crop plants, preferably on uncultivated land and plantation crops, but also for control of harmful plants before the sowing of the subséquent crop plant, such as, in particular, for préparation for seeding (burn-down application).
The active ingrédient combinations of the invention may either take the form of mixed formulations of the two components, if appropriate with further active ingrédients, additives and/or customary formulation auxîliaries, which are then applied in a customary manner diiuted with water, or can be prepared as what are called tankmixes by joint dilution of the separately formulated or partiaily separately formulated components with water.
The compounds (A) and (B) or their combinations can be formulated in varions ways accordîng to which biological and/or physicochemical parameters are required. Examples of general formulation options are: wettable powders (WP), water-soluble powders (SP), emulsifiable concentrâtes (EC), water-soluble concentrâtes, aqueous solutions (SL), émulsions (EW), such as oil-in-water and water-in-oil émulsions, sprayable solutions or émulsions, dispersions based on oil or water, oil dispersions (OD), suspoemulsions, suspension concentrâtes (SC), oil-miscible solutions, capsule suspensions (CS), dusting products (DP), dressings, granules for soil application or scattering, granules (GR) în the form of microgranules, spray granules, absorption and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules or waxes.
The invention therefore also provides herbicidal and plant-growth-regulating compositions contaîning the active ingrédient combinations of the invention.
The individual types of formulation are known in principle and are described, for example, in: WinnackerKüchler, Chemische Technologie [Chemical Technology], Volume 7, C. Hanser Verlag Munich, 4th Ed. 1986; van Valkenburg, Pesticides Formulations, Marcel Dekker, N.Y., 1973; K. Martens, Spray Drying Handbook, 3rd Ed. 1979, G. Goodwin Ltd. London.
The formulation auxîliaries required, such as inert materials, surfactants, solvents and further additives, are likewise known and are described, for example, in: Watkins, Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed.,· Darland Books, Caldwell N.J.; H.v. Olphen, Introduction to Clay Colloid
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Chemistry; 2nd Ed., J. Wiley & Sons, N.Y. Marsden, Solvents Guide, 2nd Ed., Interscience, N.Y. 1963;
McCutcheon s Détergents and Emulsifiers Annual, MC Publ. Corp., Ridgewood N.J.; Sisley and Wood, Encyclopedia of Surface Active Agents, Chem. Publ. Co. Inc., N.Y. 1964, Schônfeldt, Grenzflàchenaktive Âthylenoxidaddukte [Interface-active Ethylene Oxide Adducts], Wiss. Verlagsgesellschaft, Stuttgart 1976, Winnacker-Küchler, Chemische Technologie, Volume 7, C. Hanser Verlag Munich, 4th Ed. 1986.
On the basis of these formulations, it is also possible to produce combinations with other pesticidally active substances, such as other herbicides, fungicides, insecticides or other pesticides (for example acaricides, nematicides, molluscicides, rodenticides, aphicides, avicides, larvicides, ovicides, bactéricides, viricides etc.), and also with fertilizers and/or growth regulators, for example in the form of a finished formulation or as a tankmix.
Wettable powders are préparations which can be dispersed uniformly in water and, in addition to the active ingrédient, apart from a diluent or inert substance, also comprise surfactants of the ionic and/or nonionic type (wetling agents, dispersants), for example polyoxyethylated alkylphenols, polyoxyethylatcd fatty alcohols, polyoxyethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, sodium lignosulfonate, sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, sodium dibutylnaphthalenesulfonate or else sodium oleoylmethyltaurate. To produce the wettable powders, the active herbicidal ingrédients are finely ground, for example in customary apparatuses such as hammer mills, blower mills and air-jet mills, and simultaneously or subsequently mixed with the formulation auxiliaries.
Emulsifiable concentrâtes are produced by dissolving the active ingrédient in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene, or else relatively high-boiling aromatîcs or bydrocarbons or mixtures of the organic solvents, with addition of one or more ionic and/or nonionic surfactants (emulsifiers). Examples of emulsifiers which may be used are: calcium alkylarylsulfonate salts, such as calcium dodecylbenzenesulfonate, or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters, for example sorbitan fatty acid esters, or for example polyoxyethylene sorbitan fatty acid esters.
Dusting products are obtained by grinding the active ingrédient with finely distributed solids, for example talc, natural clays, such as kaolin, bentonite and pyrophyilite, or diatomaceous earth.
Suspension concentrâtes may be water- or oîl-based. They may be produced, for example, by wet-grinding by means of commercial bead mills and optîonal addition of surfactants as already listed above, for example, for the other formulation types.
Emulsions, for example oil-in-water émulsions (EW), can be produced, for example, by means of stirrers,
103 colloid mills and/or static mixers using aqueous organic solvents and optionally surfactants as already
Iisted above, for example, for the other formulation types.
Granules can be produced either by spraying the active ingrédient onto granular inert material capable of adsorptîon or by applying active ingrédient concentrâtes to the surface of carrier substances, such as sand, kaolinites or granular inert material, by means of adhesives, for example polyvinyl alcohol, sodium polyacrylate or else minerai oils. Suitable active ingrédients can also be granulated in the manner customary for the production of fertilizer granules - if desired as a mixture with fertilizers.
Water-dispersible granules are produced generally by processes such as spray-drying, fluidized bed granulation, pan granulation, mixing with high-speed mixers and extrusion without solid inert material.
The agrochemîcal préparations generally contain 0.1 to 99 per cent by weight, especially 0.2% to 95% by weight, of active ingrédients of types (A) and/or (B), the following concentrations being customary, depending on the type of formulation:
In wcttable powders, the active ingrédient concentration îs, for example, about 10% to 95% by weight, the remainder to 100% by weight consisting of customary formulation constituents. In the case of emulsifiable concentrâtes, the active ingrédient concentration may be about 1% to 90% by weight, preferably 5 to 80 per cent by weight.
Formulations in the form of dusts usually contain 5% to 20% by weight of active ingrédient; sprayable solutions contain about 0.05 to 80, preferably 2 to 50, per cent by weight (% by weight) of active ingrédient.
In the case of granules such as dispersible granules, the active ingrédient content dépends partially on whether the active compound îs in liquid or solid form and on which granulation auxiliaries and fi 11ers are used. In general, the content in the water-dispersible granules is between 1% and 95% by weight, preferably between 10% and 80% by weight.
In addition, the active ingrédient formulations mentioned optionally comprise the respectively customary adhesives, wetting agents, dispersants, emulsifiers, pénétrants, preservatives, antifreeze agents and solvents, fillers, colorants and carriers, antifoams, évaporation inhibitors and pH- or viscosity-modifying agents.
For application, the formulations in commercial form are, if appropriate, diluted in a customary manner, for example in the case of wettable powders, emulsifiable concentrâtes, dispersions and water-dispersible granules with water. Dust-type préparations, granules for soi! application or broadcasting and sprayable solutions are not normally diluted further with other inert substances prior to application.
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The active ingrédients can be deployed onto the plants, plant parts, plant seeds or the area under cultivation (soil), preferably on the green plants and plant parts, and optionally additionally onto the soil.
One possible use is the joint application of the active ingrédients in the form of tankmixes, where the optimally formulated concentrated formulations of the individual active ingrédients together are mixed in a tank with water, and the spray liquor obtained is deployed.
A joint herbicidal formulation of the inventive combination of active ingrédients (A) and (B) has the advantage that it can be applied more easily since the quantities of the components are already set at the correct ratio to one another. Moreover, the auxiliaries in the formulation can be adjusted optimally to one another, whereas a tank mix of different formulations may resuit in unwanted combinations of auxiliaries.
A. General formulation examples
a) A dusting product is obtained by mixing 10 parts by weight of an active ingrédient (A) or (B) or an active ingrédient mixture (A) + (B) (and optionally further active ingrédient components) and/or salts thereof and 90 parts by weight of talc as inert substance, and comminuting in a beater mill.
b) A wettable powder which is readily dispersible in water is obtained by mixing 25 parts by weight of an active ingredient/active ingrédient mixture, 64 parts by weight of kaolin-containing quartz as inert substance, 10 parts by weight of potassium lignosulfonate and 1 part by weight of sodium oleoylmethyitaurate as wetting agent and dispersant, and grinding the mixture in a pinned-disk mill.
c) A dispersion concentrate which is readily dispersible in water is obtained by mixing 20 parts by weight of an active ingredient/active ingrédient mixture with 6 parts by weight of alkylphenol polyglycol ether (Triton® X 207), 3 parts by weight of isotridecanol polyglycol ether (8 EO) and 71 parts by weight of paraffinic minerai oil (boiling range for example approximately 255 to 277°C) and grinding the mixture in a friction bail mill to a fineness of below 5 microns.
d) An emulsifiable concentrate is obtained from 15 parts by weight of an active ingredient/active ingrédient mixture, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of oxyethylated nonylphenol as emulsifier.
e) Water-dispersible granules are obtained by mixing parts by weight of an active ingredient/active ingrédient mixture, parts by weight of calcium lignosulfonate, parts by weight of sodium lauryl sulfate, parts by weight of polyvinyl alcohol and parts by weight of kaolin,
105 grinding the mixture in a pinned-dîsk mill, and granulatiog the powder in a fluidîzed bed by spray application of water as a granulating liquid.
f) Water-dispersible granules are also obtained by homogenizing and precomminuting, in a colloid mill, parts by weight of an active ingredient/active ingrédient mixture, parts by weight of sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, parts by weight of sodium oleoylmethyltaurate, part by weight of polyvinyl alcohol, parts by weight of calcium carbonate and parts by weight of water, then grinding the mixture in a bead mill and atomizing and drying the resulting suspension in a spray tower by means of a one-phase nozzle.
B . Biological examples
On employaient of the combinations of the invention, herbicidal effects on a harmful plant species that exceed the formai sum total of the effects of the herbicides présent when applied alone are frequently observed. Alternatively, in some cases, it is possible to observe that a smaller application rate for the herbicide combination is required in order to achîeve the same effect for a harmful plant species compared to the individual préparations. Such increases in action or increases in effeciiveness or réductions in application rate are a strong indication of a synergistic effect.
When the observed efficacies already exceed the formai sum total of the values of the tests with individual applications, they also exceed the expected value according to Colby, which is calculated using the formula below and is likewise regarded as an indication of synergism (cf. S. R. Colby; in Weeds 15 (1967) pp. 20 to 22):
Ec = A+B - (A-B/100) where:
A - efficacy of the active ingrédient (A) in % at an application rate of a g a.i./ha;
B = efficacy of the active ingrédient (B) in % ai an application rate of b g a.i./ha;
Ec = expected value of the effect of the combination (A)+(B) in % at the combined application rate a+b g a.i./ha.
The observed values (EA) from the experiments, given suitable low dosages, show an effect of the combinations exceeding the expected values according to Colby (Δ).
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1. Post-emergence action against weeds
Seeds or rhizome pièces of mono- and dicotyledonous weeds are placed in sandy loam in pots, covered with soil and grown in a greenhouse under good growth conditions (température, air humidity, water supply). Three weeks after sowing, the test plants are treated at the three-leaf stage with the compositions of the invention. The compositions of the invention, formulated as spray powders or as émulsion concentrâtes, are sprayed onto the green plant parts in various dosages with an application rate équivalent to 300 to 800 1/ha of water. After the test plants hâve been left to stand in the greenhouse under optimal growth conditions for about 3 to 4 weeks, the action of the préparations is scored visually in comparison to untreated Controls. The compositions of the invention also hâve good post-emergence herbicidal activity against a broad spectrum of economically important weed grasses and broadleaved weeds.
Effects of the combinations of the invention that exceed the formai sum total of the effects in the case of individual application of the herbicides are frequently observed here. The observed values from the experiments, given suitable low dosages, show an effect of the combinations exceeding the expected values according to Colby.
2. Herbicidal pre-emergence and post-emergence action (field trials)
The experiments were conducted on outdoor plots in accordance with the greenhouse experiments from section 1. The rating was analogous to the experiment in section 1.
3. Herbicidal action and crop plant compatibility (field trials)
Crop plants were grown in outdoor plots under natural outdoor conditions, by laying out seeds or rhizome pièces of typical harmful plants or utilizing natural weed flora. The treatment with the compositions of the invention foilowed the emergence of the harmful plants and of the crop plants, generally at the 2- to 4-leaf stage; in some cases (as specified), individual active ingrédients or active ingrédient combinations were applied pre-emergence or as a sequentîal treatment parti y pre-emergence and/or post-emergence.
In the case of plantation crops, în general, only the soil between the individual crop plants was treated with the active ingrédients.
After application, for example 2, 4, 6 and 8 weeks after application, the effect of the préparations was rated visually by comparison with untreated Controls. The compositions of the invention also hâve synergistic herbicidal activity in field trials against a broad spectrum of economically important weed grasses and broadleaved weeds. The comparison showed that the combinations of the invention usually hâve greater, and in some cases considerably greater, herbicidal action than the sum total of the effects of the individual herbicides, and therefore suggests synergism. The effects over significant parts of the rating period were also above the expected values according to Colby, and therefore likewise suggest synergism.
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The crop plants, by contrast, were damagcd only insignifîcantly, if at ail, as a resuit of the treatments with the herbicidal products.
4. Spécifie trial ex amp les
The following abbreviations are used in the description and the tables that follow:
g a.i./ha = grams of active substance (active ingrédient) (- 100% active ingrédient) per hectare;
The sum total of the effects of the individual applications is reported under EA; cxpected values according to Colby are each reported under Ec.
The biological results of the compositions according to the invention are summarized in Tables 3.1-3.2. The rating period is reported in days after application (DAT).
Table 3.1: Synergistic effect (Δ) for herbicidal binary compositions comprising herbicides from group B2, applied by the post-emergence method
| Active ingredient(s) (Z5) | Application rate [g a.i./ha] | Herbicidal action 21 DAT [%] against Setaria viridis |
| (B2.18) Diflufenican | 90 30 | 20 10 |
| Al | 5 1.7 | 90 85 |
| Al + (B2.18) Diflufenican | 5 + 90 1.7 + 90 5 + 30 1.7 + 30 | EA = 98 (Εε = 88)Δ 10 EA = 97 (EC = 91)A6 EA = 95 (Ec = 86.5) Δ 8 |
| Active ingredient(s) (Z5) | Application rate [g a.i./ha] | Herbicidal action 21 DAT [%] against Abutilon theophrasti |
| 270 | 30 | |
| (B2.18) Diflufenican | 90 | 20 |
| 30 | 20 | |
| Al | 5 | 60 |
| Al | 5 + 270 | EA = 85 (EC=72)A 13 |
| + | 5 + 90 | EA = 85 (Ec = 68) Δ 17 |
| (B2.18) Diflufenican | 5 + 30 | EA = 85 (Ec = 68) Δ 17 |
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| Active ingredient(s) (Z5) | Application rate [g a.i./ha] | Herbicidal action 21 DAT [%] against Kochia Scoparia |
| (B2.18) Diflufenican | 270 90 30 | 25 20 10 |
| Al | 45 15 5 | 85 80 75 |
| Al + (B2.18) Diflufenican | 45 + 270 15 + 270 5 + 270 15 + 90 5 + 90 45 + 30 15 + 30 5 + 30 | ΕΛ = 95 (EC = 88)A6 ΕΛ = 95 (Ec= 85) Δ 10 EA = 93 (EC=81)A 11 ΕΛ - 93 (Ec = 84 ) Δ 9 EA = 90 (Ec = 80) Δ 10 EA - 93 (Ec = 86) Δ 6 EA = 90 (Ec = 82) Δ 8 EA - 85 (Ec = 77) Δ 7 |
| Active ingredîent(s) (Z5) | Application rate [g a.i./ha] | Herbicidal action 21 DAT [%] against Ipomoea purpurea |
| (B2.18) Diflufenican | 270 30 | 60 30 |
| Al | 15 5 | 80 80 |
| Al + (B2.18) Diflufenican | 15 + 270 15 + 30 5 + 30 | EA - 99 (Ec = 92) Δ 7 EA - 97 (EC=86)A 11 EA = 93 (EC = 86)A7 |
| Active ingredient(s) (Z5) | Application rate [g a.i. / ha] | Herbicidal action 14 DAT [%] against Alopecurus myosuroides |
| Al | 16 4 | 85 80 |
| (B2.18) Diflufenican | 90 30 | 20 20 |
| Al + (B2.18) Diflufenican | 16 + 90 4 + 90 4 + 30 | EA - 93 (EC = 88)A = 5 EA = 90 (Ec = 84) Δ = 6 EA = 93 (Ec = 84) Δ = 9 |
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| Active ingredient(s) (Z5) | Application rate [g a.i. / ha] | Herbicidal action 28 DAT [%] against Alopecitrus myosuroides |
| Al | 4 | 85 |
| (B2.18) Dîflufenican | 270 | 20 |
| Al + (B2.18) Dîflufenican | 4 + 270 | EA - 95 (ΕΓ = 88)Δ = 7 |
| Active ingredient(s) (Z5) | Application rate [g a.i. / ha] | Herbicidal action 14 DAT [%] against Lolium rigidwH |
| Al | 4 | 70 |
| (B2.18) Dîflufenican | 270 90 | 20 20 |
| Al + (B2.18) Dîflufenican | 4 + 270 4 + 90 | EA - 85 (Ec = 76) Δ = 9 ΕΛ = 90 (EC=76)A- 14 |
| Active ingredient(s) (Z5) | Application rate [g a.i. / ha] | Herbicidal action 28 DAT [%] against Lolium rigidum |
| Al | 4 | 75 |
| (B2.18) Dîflufenican | 270 | 30 |
| Al + (B2.18) Dîflufenican | 4 + 270 | EA = 93 (EC = 83)A= 10 |
| Active ingredient(s) (Z5) | Application rate [g a.i. / ha] | Herbicidal action 14 DAT [%] against Matricaria inodora |
| Al | 4 | 70 |
| (B2.18) Dîflufenican | 270 | 30 |
| Al + (B2.18) Dîflufenican | 4 + 270 | EA = 90 (Ec = 79) Δ = 1 1 |
110
| Active ingredient(s) (Z5) | Application rate [g a.i. / ha] | Herbicidal action 28 DAT ]%] against Matricaria inodora |
| Al | 16 | 85 |
| (B2.18) Diflufenican | 270 | 20 |
| Al + (B2.18) Diflufenican | 16 + 270 | EA — 97 (ec = 88)A = 9 |
| Active ingredient(s) (Z5) | Application rate [g a.i. / ha] | Herbicidal action 14 DAT f%] against Phalaris minor |
| Al | 4 1 | 75 30 |
| (B2.18) Diflufenican | 30 270 | 20 30 |
| Al + (B2.18) Diflufenican | 4 + 30 1+270 | EA = 85 (Ec = 80) Δ = 5 EA = 75 (EC = 51)A = 24 |
| Active ingredîent(s) (Z5) | Application rate [g a.i. / ha] | Herbicidal action 28 DAT [%] against Phalaris tninor |
| Al | 16 4 | 85 70 |
| (B2.18) Diflufenican | 270 90 30 | 30 10 10 |
| Al + (B2.18) Diflufenican | 16 + 270 16 + 90 16 + 30 4 + 270 4 + 90 4 + 30 | m w rn ^ > > > Il II H ...... υί ΙΛ 1¾ ni ni n η ° η η n ......... II W Ü Îo ?? 3 S >>>[>>> ...... ...... C S J K 56 ,J' |
111
| Active ingredient(s) (Z5) | Application rate [g a.i. /ha] | Herbicidal action 14 DAT [%] against Poa anima L. |
| Al | 16 4 | 80 80 |
| (B2.18) Diflufenican | 90 | 20 |
| Al + (B2.18) Diflufenican | 16 + 90 4 + 90 | ΕΛ = 90 (Ec = 84) Δ = 6 EA = 90 (Ec = 84) Δ = 6 |
| Active ingredient(s) (Z5) | Application rate [g a.i. / ha] | Herbicidal action 28 DAT f%] against Poa aiinita L. |
| Al | 4 | 85 |
| 1 | 30 | |
| 270 | 30 | |
| (B2.18) Diflufenican | 90 | 20 |
| 30 | 10 | |
| 4 + 270 | EA = 97 (Ec = 90) Δ = 7 | |
| Al | 4 + 90 | EA = 97 (EC = 88)A = 9 |
| + | 4 + 30 | EA - 97 (Ec = 87)A = 10 |
| (B2.18) Diflufenican | 1 + 270 | EA - 60 (EC = 51)A=9 |
| 1+90 | EA = 50 (Ec = 44) Δ = 6 |
| Active ingredient(s) (Z5) | Application rate [g a.i. / ha] | Herbicidal action 14 DAT f%] against Veronica hederifolia |
| Al | 1 | 30 |
| (B2.18) Diflufenican | 270 | 30 |
| Al + (B2.18) Diflufenican | 1 + 270 | EA = 60 (EC = 51)A = 9 |
112
| Active ingredient(s) (Z5) | Application rate [g a.i. / ha] | Herbicidal action 28 DAT [%] against Veronica hederifolia |
| Al | 4 | 40 |
| 270 | 30 | |
| (B2.18) Diflufenican | 90 | 20 |
| 30 | 20 | |
| Al | 4 + 270 | EA = 85 (Ec = 58) Δ = 27 |
| + | 4 + 90 | EA = 60 (Ec = 52) Δ = 8 |
| (B2.18) Diflufenican | 4 + 30 | EA = 70 (Ec = 52) Δ = 18 |
Table 3.2: Synergistic effect (Δ) for herbicidal binary compositions comprising herbicides from group B7, applied by the post-emergence method
| Active ingredient(s) (Z25) | Application rate [g a.i./ha] | Herbicidal action 21 DAT [%] against Kochia Scoparia |
| (B7.4) Glufosinate [CAS 77182-82-2] | 150 50 | 50 10 |
| Al | 15 5 | 80 75 |
| Al + (B7.4) Glufosinate [CAS 77182-82-2] | 5 + 150 15 + 50 5 + 50 | EA = 93 (Ec = 87) Δ 5 EA = 90 (Ec = 82) Δ 8 EA = 90 (Ec = 77) Δ 12 |
| Active ingredient(s) (Z25) | Application rate [g a.i./ha] | Herbicidal action 21 DAT [%] against A butilon theophrasti |
| (B7.4) Glufosinate [CAS 77182-82-2] | 50 | 50 |
| Al | 5 | 60 |
| Al + (B7.4) Glufosinate [CAS 77182-82-2] | 5 + 50 | EA = 90 (Ec = 80) Δ 10 |
| Active ingredient(s) (Z25) | Application rate [g a.i./ha] | Herbicidal action 21 DAT [%] against Amaranthus pabneri |
| (B7.4) Glufosinate | 150 | 90 |
113
| [CAS 77182-82-2] | 50 | 35 |
| Al | 15 5 | 40 30 |
| Al + (B7.4) Glufosinate [CAS 77182-82-2] | 15 + 150 5 + 150 5 + 50 | EA = 100 (Ec = 94) Δ 6 EA= 100 (EC = 93)A 7 EA = 60 (Ec = 54) Δ 5 |
| Active ingredient(s) (Z25) | Application rate [g a.i. / ha] | Herbicidal action 14 DAT [%] against Centaurea cyamis |
| Al | 1 | 10 |
| (B7.4) Glufosinate [CAS 77182-82-2] | 540 180 | 85 60 |
| Al + (B7.4) Glufosinate [CAS 77182-82-2] | 1 + 540 1 + 180 | EA = 95 (Ec = 87) Δ = 8 EA = 70 (Ec = 64) Δ = 6 |
| Active ingredientfs) (Z25) | Application rate [g a.i. / ha] | Herbicidal action 28 DAT [%] against Centaurea cyaiius |
| Al | 1 | 10 |
| (B7.4) Glufosinate [CAS 77182-82-2] | 540 180 | 70 30 |
| Al + (B7.4) Glufosinate [CAS 77182-82-2] | 1+540 1 + 180 | EA = 95 (Ec = 73)à = 22 EA = 50 (Ec = 37) Δ = 13 |
114
| Active ingredient(s) (Z25) | Application rate [g a.i. / ha] | Herbicidal action 14 DAT [%] against Lolium rigidum |
| Al | 16 | 80 |
| (B7.4) Glufosinate [CAS 77182-82-2] | 18Ü | 40 |
| Al 4- (B7.4) Glufosinate [CAS 77182-82-21 | 16 + 180 | ΕΛ = 93 (Ec = 88) Δ = 5 |
| Active ingredient(s) (Z25) | Application rate [g a.i. / ha] | Herbicidal action 28 DAT [%] against Lolium rigidum |
| Al | 4 1 | 75 30 |
| (B7.4) Glufosinate [CAS 77182-82-2] | 540 | 40 |
| Al + (B7.4) Glufosinate [CAS 77182-82-2] | 4 + 540 1+540 | EA = 97 (EC = 85)A=12 EA = 70 (EC = 58)A= 12 |
| Active ingredient(s) (Z25) | Application rate [g a.i. / ha] | Herbicidal action 14 DAT [%] against Lolium rigidum (résistant biotype) |
| Al | 1 | 20 |
| (B7.4) Glufosinate [CAS 77182-82-2] | 540 | 50 |
| Al + (B7.4) Glufosinate [CAS 77182-82-2] | 1 + 540 | EA - 80 (Ec = 60) Δ = 20 |
115
| Active ingredîent(s) (Z25) | Application rate [g a.i. / ha] | Herbicidal action 28 DAT [%] against Latium rigidum (résistant biotype) |
| Al | 4 1 | 40 20 |
| (B7.4) Glufosinate [CAS 77182-82-2] | 540 | 30 |
| Al + (B7.4) Glufosinate [CAS 77182-82-2] | 4 + 540 1 + 540 | EA = 70 (EC=58)A = 12 EA = 50 (Ec = 44) Δ = 6 |
| Active îngredient(s) (Z25) | Application rate [g a.i. / ha] | Herbicidal action 28 DAT [%] against Matricaria inodora |
| Al | 16 i | 85 50 |
| (B7.4) Glufosinate [CAS 77182-82-2] | 180 | 60 |
| Al + (B7.4) Glufosinate [CAS 77182-82-2] | 16 + 180 1 + 180 | EA= 100 (EC = 94)A = 6 EA = 99 (Ec=80)A = 19 |
| Active ingredient(s) (Z25) | Application rate [g a.i. / ha] | Herbicidal action 14 DAT [%] against Phalaris minor |
| Al | 4 1 | 75 30 |
| (B7.4) Glufosinate [CAS 77182-82-2] | 60 540 | 20 60 |
| Al (B7.4) Glufosinate [CAS 77182-82-2] | 4 + 60 1+540 | EA = 90 (Ec = 80) Δ = 10 EA - 80 (Ec = 72)Δ - 8 |
116
| Active ingredient(s) | Application rate | Herbicidal action 28 DAT [%] against |
| (Z25) | [g a.i./ha] | Pha taris minor |
| Δ 1 | 16 | 85 |
| 4 | 70 | |
| 540 | 40 | |
| (B7.4) Glufosinate | 180 | 30 |
| [CAS 77182-82-2] | 60 | 10 |
| Al | 16 + 540 | EA = 97 (EC = 91)A = 6 |
| + | 16 + 180 | EA = 95 (Ec = 90) Δ = 5 |
| (B7.4) Glufosinate | 16 + 60 | EA = 95 (EC = 87)A = 8 |
| [CAS 77182-82-2] | 4 + 60 | EA = 80 (EC = 73)A = 7 |
| Active ingredient(s) (Z25) | Application rate [g a.i. / ha] | Herbicidal action 28 DAT [%[ against Poa annua L. |
| Al | 4 | 85 |
| (B7.4) Glufosinate [CAS 77182-82-2] | 180 | 20 |
| Ai + (B7.4) Glufosinate [CAS 77182-82-2] | 4+180 | EA = 95 (EC = 88)A = 7 |
| Active ingredient(s) (Z25) | Application rate [g a.i. / ha] | Herbicidal action 14 DAT [%] against Veronica hederifolia |
| Al | 16 | 70 |
| (B7.4) Glufosinate [CAS 77182-82-21 | 60 | 50 |
| Al + (B7.4) Glufosinate [CAS 77182-82-2] | 16 + 60 | EA = 97 (EC=85)A = 12 |
Π7
| Active ingredient(s) (Z26) | Application rate [g a.i./ha] | Herbicidal action 45 DAT [%] against Amarandius tuberculatus |
| (B7.5) Glyphosate [CAS 38641-94-01 | 720 | 15 |
| Al | 100 | 57 |
| Al + (B7.5) Glyphosate [CAS 38641-94-01 | 100 + 720 | EA = 73 (EC = 63 )A 10 |
| Active ingredient(s) (Z26) | Application rate [g a.i./ha] | Herbicidal action 45 DAT [%] against Ipomoea ssp |
| (B7.5) Glyphosate [CAS 38641-94-01 | 720 | 0 |
| Al | 100 | 57 |
| Al + (B7.5) Glyphosate [CAS 38641-94-01 | 100 + 720 | EA = 70 (EC = 57)A 13 |
| Active ingredient(s) (Z26) | Application rate [g a.i./ha] | Herbicidal action 16 DAT [%] against Richardia scabra |
| (B7.5) Glyphosate [CAS 38641-94-0] | 720 | 62 |
| Al | 100 | 48 |
| Al + (B7.5) Glyphosate [CAS 38641-94-0] | 100 + 720 | EA = 92 (Ec = 80) Δ 12 |
| Active ingredient(s) (Z26) | Application rate [g a.i./ha] | Herbicidal action 42 DAT [%] against Géranium dissectum |
| (B7.5) Glyphosate [CAS 38641-94-0] | 720 | 50 |
| Al | 100 | 17 |
| Al + (B7.5) Glyphosate [CAS 38641-94-0] | 100 + 720 | EA= 100 (EC = 59)A41.5 |
118
| Active ingredient(s) (Z26) | Application rate [g a.i./ha] | Herbicidal action 45 DAT [%] against Lysimachia mimmularia |
| (B7.5) Glyphosate [CAS 38641-94-01 | 720 | 7 |
| Al | 100 | 25 |
| Al + (B7.5) Glypliosate [CAS 38641-94-0] | 100 + 720 | EA = 60 (EC = 3O)A3O |
| Active ingredient(s) (Z26) | Application rate [g a.i./ha] | Herbicidal action 42 DAT [%] against Malva piisilla |
| (B7.5) Glyphosate [CAS 38641-94-0] | 720 | Ü |
| Al | 100 | ü |
| Al + (B7.5) Glyphosate [CAS 38641-94-0] | 100 + 720 | EA = 100 (Ec = 0) Δ 100 |
| Active ingredient(s) (Z26) | Application rate [g a.i./ha] | Herbicidal action 21 DAT [%] against Amaranthus pabneri |
| (B7.5) Glyphosate [CAS 38641-94-0] | 50 | 60 |
| Al | 5 | 30 |
| Al + (B7.5) Glyphosate [CAS 38641-94-0] | 5 + 50 | EA = 85(EC = 72) Δ 13 |
| Active ingredient(s) (Z26) | Application rate [g a.i./ha] | Herbicidal action 21 DAT [%] against Kochia Scoparia |
| (B7.5) Glyphosate [CAS 38641-94-0] | 150 | 20 |
| Al | 15 | 80 |
| Al + (B7.5) Glyphosate [CAS 38641-94-0] | 15 + 150 | EA = 90 (Ec = 84) Δ 6 |
119
| Active ingredient(s) (Z26) | Application rate [g a.i./ha] | Herbicidal action 28 DAT [%] against B rem ms sterilis |
| Al | 1 | 30 |
| (B7.5) Glyphosate [CAS 38641-94-0] | 450 150 | 90 80 |
| Al + (B7.5) Glyphosate [CAS 38641-94-0] | 1 + 450 1 + 150 | EA = 98 (ΕΟ = 93)Δ = 5 EA = 93 (Ec = 86) Δ = 7 |
| Active ingredient(s) (Z26) | Application rate [g a.i. / ha] | Herbicidal action 14 DAT [%] against Centaurea cyanus |
| 16 | 40 | |
| Al | 4 | 30 |
| 1 | 10 | |
| (B7.5) Glyphosate | 450 | 60 |
| [CAS 38641-94-0] | 150 | 50 |
| 16 + 450 | EA = 90 (Ec = 76) Δ = 14 | |
| Al | 16 + 150 | EA = 75 (Ec = 70) Δ = 5 |
| + | 4 + 450 | EA = 85 (ΈΓ = 72)Δ= 13 |
| (B7.5) Glyphosate | 4 + 150 | EA = 80 (EC = 65)A = 15 |
| [CAS 38641-94-0] | 1 + 450 | EA = 80 (EC = 64)A = 16 |
| 1 + 150 | EA = 75 (ΕΓ = 55)Δ = 20 |
| Active ingredient(s) (Z26) | Application rate [g a.i. / ha] | Herbicidal action 28 DAT [%] against Centaurea cyanus |
| Al | 16 4 1 | 50 30 10 |
| (B7.5) Glyphosate [CAS 38641-94-0] | 450 150 50 | 60 40 10 |
| Al + (B7.5) Glyphosate [CAS 38641-94-0] | 16 + 450 4 + 150 1 + 450 1 + 150 1 + 50 | 'G Γ1 Tt — — ri ri η n Il II II II II 1 < < < < < O 00 sO X 'G Ό Τ’ — Il II II II II U W O U WW WWW ιη ο ο o ο, oo m r τ Il n II II H < < < « < w w w w w |
120
| Active ingredient(s) (Z26) | Application rate [g a.î. ! ha] | Herbicidal action 28 DAT [%] against Lolium rigidum |
| Al | 1 | 30 |
| (B7.5) Glyphosate [CAS 38641-94-0] | 150 | 30 |
| Al 4- (B7.5) Glyphosate [CAS 38641-94-0] | 1 + 150 | EA = 60 (EC = 51)A = 9 |
| Active ingredient(s) (Z26) | Application rate [g a.i. / ha] | Herbicidal action 28 DAT [%] against Lolium rigidum (résistant biotype) |
| Al | 4 | 40 |
| (B7.5) Glyphosate [CAS 38641-94-0] | 450 | 70 |
| Al + (B7.5) Glyphosate [CAS 38641-94-01 | 4 + 450 | EA = 95(EC=82) Δ=13 |
| Active ingredient(s) (Z26) | Application rate [g a.i. / ha] | Herbicidal action 28 DAT [%1 against Matricaria inodora |
| Al | 1 | 50 |
| (B7.5) Glyphosate [CAS 38641-94-01 | 150 | 70 |
| Al + (B7.5) Glyphosate [CAS 38641-94-01 | 1 + 150 | EA = 90(Ec = 85) Δ =5 |
121
| Active ingredient(s) (Z26) | Application rate [g a.i. / ha] | Herbicidal action 28 DAT [%] against Phalaris minor |
| Al | 16 | 85 |
| (B7.5) Giyphosate [CAS 38641-94-0] | 50 | 30 |
| Al + (B7.5) Giyphosate [CAS 38641-94-0] | 16 + 50 | EA = 95 (Ec = 90) Δ = 5 |
| Active ingredient(s) (Z26) | Application rate [g a.i. / ha] | Herbicidal action 28 DAT [%] against Poa anima L. |
| Al | 1 | 30 |
| (B7.5) Giyphosate [CAS 38641-94-0] | 450 | 85 |
| Al + Giyphosate [CAS 38641-94-01 | 1 + 450 | EA = 98(Ec = 90) Δ = 8 |
Further biological results of the compositions according to the invention are summarized in Tables 3.33.4. The rating period is reported in days after application (DAT).
Table 3.3: Synergistic effect (Δ) for herbicidal binary compositions comprising herbicide Al, applied by the post-emergence method
| Active ingrédient | Application rate /ha | Herbicidal action 28 DAT against Centaurea cyanus |
| A1 | 4 1 | 50 40 |
| 50 450 | 30 70 | |
| A1 + (B3.1) Bromoxynil | 4 + 50 1 + 450 1 + 50 | EA = 80 (Ec = 65) Δ = 15 EA = 98 (Ec = 82) Δ = 16 EA = 65 (Ec = 58) Δ = 7 |
| Active ingrédient | Application rate / ha | Herbicidal action 28 DAT against Lolium rigidum |
| Al | 4 | 50 |
| 450 150 | 20 15 |
122
| A1 + (B3.1 ) Bromoxynil | 4 + 450 4+150 | EA = 65 (Ec = 60) Δ = 5 EA = 85 (Ec = 58) Δ = 27 |
| Active ingrédient | Application rate g a.i, l ha | Herbicidal action 28 DAT against Lolium rigidum (résistant biotype) |
| A1 | 1 | 5 |
| 150 50 | 0 0 | |
| A1 + (B3.1) Bromoxynil | 1 + 150 1 + 50 | EA=10(Ec = 5) Δ = 5 EA=10(Ec = 5) Δ = 5 |
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Lolium rigidum (résistant biotype) |
| A1 | 16 | 80 |
| (B3.1 ) Bromoxynil | 450 50 | 25 0 |
| A1 + (B3.1 ) Bromoxynil | 16 + 450 16 + 50 | EA = 93 (Ec = 85) Δ = 8 EA = 85 (Ec =80) Δ = 5 |
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Poa annua L, |
| A1 | 16 | 75 |
| 1 | 20 | |
| 450 | 25 | |
| 150 | 0 | |
| 50 | 0 | |
| A1 + (B3.1) Bromoxynil | 16 + 450 | EA = 97 (Ec = 81) Δ= 16 |
| 16 + 150 | EA = 85 (Ec = 75) Δ = 10 | |
| 16 + 50 | EA = 97 (Ec = 75) Δ = 22 | |
| 1 + 150 | EA = 35(Ec = 20) Δ = 15 |
| Active ingrédient | Application rate g a.i. | Herbicidal action 28 DAT against Veronica hederifolia |
| A1 | 1 | 80 |
| 150 | 20 | |
| A1 + (B3.1) Bromoxynil | 1 + 150 | EA = 93 (Ec = 84) Δ = 9 |
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Viola tricolor |
| A1 | 16 | 75 |
| 450 | 40 | |
| A1 + (B3.1 ) Bromoxynil | 16 + 450 | EA = 90 (Ec = 85) Δ = 5 |
| Active ingrédient | Application rate g a.i. ! ha | Herbicidal action 28 DAT against Bromus sterilis |
| A1 | 4 | 70 |
| 100 | 40 | |
| A1 + (B2.28) Flufenacet | 4 + 100 | EA = 90 (Ec = 82) Δ = 8 |
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Lolium rigidum (résistant biotype) |
| A1 | 4 | 50 |
| (B2.28) Flufenacet | 100 33 | 65 15 |
123
| A1 + (B2.28) Flufenacet | 4 + 100 4 + 33 | EA = 93 (Ec = 83) Δ = 10 EA = 95 (Ec = 58) Δ = 37 |
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Matricaria inodora |
| A1 | 16 | 80 |
| 1 | 30 | |
| 300 | 40 | |
| 100 | 20 | |
| 33 | 15 | |
| A1 + (B2.28) Flufenacet | 16 + 300 | EA = 95 (Ec = 88) Δ = 7 |
| 16 + 100 | EA = 95 (Ec = 84) Δ = 11 | |
| 16 + 33 | EA = 95 (Ec = 83) Δ = 12 | |
| 1 + 300 | EA - 65 (Ec = 58) Δ = 7 | |
| 1 + 100 | EA = 60 (Ec = 44) Δ = 16 | |
| 1 + 33 | EA = 75 (Ec = 41) Δ = 34 |
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Poa annua L. |
| A1 | 16 | 75 |
| (B2.28) Flufenacet | 33 | 20 |
| A1 + (B2.28) Flufenacet | 16 + 33 | EA = 95 (Ec = 80) Δ= 15 |
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Veronica hederifolia |
| A1 | 1 | 80 |
| (B2.28) Flufenacet | 100 | 50 |
| A1 + (B2.28) Flufenacet | 1+100 | EA = 95 (Ec = 90) Δ = 5 |
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Viola tricolor |
| A1 | 16 | 75 |
| 1 | 50 | |
| (B2.28) Flufenacet | 300 | 50 |
| 100 | 20 | |
| 33 | 15 | |
| A1 + (B2.28) Flufenacet | 16 + 300 | EA = 95 (Ec = 88) Δ = 7 |
| 16+100 | EA = 85 (Ec = 80) Δ = 5 | |
| 16 + 33 | EA = 97 (Ec = 79) Δ= 18 | |
| 1 + 100 | EA = 80 (Ec = 60) Δ = 20 | |
| 1 + 33 | EA = 65 (Ec = 58) Δ = 7 |
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Matricaria inodora |
| A1 | 1 | 30 |
| (B2.31) Forainsulfuron | 9 | 65 |
| A1 + (B2.31) Foramsulfuron | 1 +9 | EA = 85 (Ec = 76) Δ = 9 |
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Phalaris minor |
| A1 | 16 | 80 |
| 4 | 80 | |
| 1 | 20 | |
| 1 | 25 |
124
| 9 | 85 | |
| A1 + (B2.31 ) Foramsulfuron | 16+1 4 + 1 1 + 9 | EA = 95 (Ec = 85) Δ = 10 EA = 90 (Ec = 85) Δ = 5 EA = 95 (Ec = 88) Δ = 7 |
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Lolium rigidum |
| A1 | 4 | 50 |
| (B5.31) Halauxifen | 9 | 25 |
| 3 | 0 | |
| 1 | 0 | |
| A1 + (B5.31) Halauxifen | 4 + 9 | EA = 70 (Ec = 63) Δ = 7 |
| 4 + 3 | EA = 80 (Ec = 50) Δ = 30 | |
| 4 + 1 | EA = 65 (Ec = 50) Δ = 15 |
| Active ingrédient | Application rate g a.i. ! ha | Herbicidal action 28 DAT against Lolium rigidum (résistant biotype) |
| A1 | 16 1 | 30 5 |
| (B5.31) Halauxifen | 1 | 0 |
| A1 + (B5.31) Halauxifen | 16 + 1 1 + 1 | EA = 35 (Ec = 30) Δ = 5 EA=15(EC = 5) Δ = 10 |
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Matricaria inodora |
| A1 | 1 | 30 |
| (B5.31 ) Halauxifen | 3 | 70 |
| A1 + (B5.31) Halauxifen | 1 +3 | EA = 90 (Ec = 79) Δ = 11 |
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Phalaris minor |
| A1 | 16 | 80 |
| (B5.31) Halauxifen | 9 | 15 |
| 3 | 10 | |
| 1 | 0 | |
| A1 + (B5.31) Halauxifen | 16 + 9 | EA = 95 (Ec = 83) Δ = 12 |
| 16 + 3 | EA = 95 (Ec = 82) Δ = 13 | |
| 16 + 1 | EA = 95 (Ec = 80) Δ = 15 |
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Poa annua L. |
| A1 | 16 | 75 |
| 1 | 20 | |
| (B5.31) Halauxifen | 9 | 15 |
| 3 | 10 | |
| 1 | 0 | |
| A1 + (B5.31) Halauxifen | 16 + 9 | EA = 95 (Ec = 79) Δ = 16 |
| 16 + 3 | EA = 90 (Ec = 78) Δ=12 | |
| 16+ 1 | EA = 90 (Ec = 75) Δ=15 | |
| 1 + 1 | EA=35(v = 20) Δ = 15 |
| Active ingrédient | Application rate g a.i. 1 ha | Herbicidal action 28 DAT against Bromus sterilis |
| A1 | 4 | 70 |
125
| (B11.6) Indaziflam | 12 | 25 |
| A1 + (B11.6) Indaziflam | 4 + 12 | EA = 90 (Ec=78) Δ = 12 |
| Active ingrédient | Application rate g a.i, / ha | Herbicidal action 28 DAT against Lamium purpureum L. |
| A1 | 1 | 80 |
| 4 | 35 | |
| A1 + (B11.6) Indaziflam | 1 + 4 | EA = 97 (Ec = 87) Δ = 10 |
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Lolium rigidum |
| Al | 4 | 50 |
| (B11.6) Indaziflam | 12 4 | 20 30 |
| Al + (B11.6) Indaziflam | 4+12 4 + 4 | EA = 80 (Ec = 60) Δ = 20 EA = 95 (Ec = 65) Δ = 30 |
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Lolium rigidum (résistant biotype) |
| A1 | 16 | 30 |
| 4 | 20 | |
| 1 | 5 | |
| (B11.6) Indaziflam | 36 | 35 |
| 12 | 30 | |
| A1 + (B11.6) Indaziflam | 16 + 36 | EA= 65 (Ec = 55) Δ = 10 |
| 4 + 12 | EA = 60 (Ec = 44) Δ = 16 | |
| 1 + 36 | EA = 70 (Ec = 38) Δ = 32 |
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Matricaria inodora |
| A1 | 16 1 | 80 30 |
| (B11.6) Indaziflam | 4 | 65 |
| A1 + (B11.6) Indaziflam | 16 + 4 1 + 4 | EA = 98 (Ec = 93) Δ = 5 EA = 95 (Ec = 76) Δ= 19 |
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Phalaris minor |
| A1 | 16 4 | 80 80 |
| (B11.6) Indaziflam | 36 4 | 60 0 |
| A1 + (B11.6) Indaziflam | 16 + 36 16 + 4 4 + 36 | EA = 97 (Ec = 92) Δ = 5 EA = 95 (Ec = 80) Δ = 15 EA = 100 (Ec = 92) Δ = 8 |
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Poa annua L. |
| A1 | 16 1 | 75 20 |
| (B11.6) Indaziflam | 4 | 20 |
| A1 + (B11.6) Indaziflam | 16 + 4 1 + 4 | EA = 85 (Ec = 80) Δ = 5 EA= 50 (Ec = 36) Δ = 14 |
126
| Active ingrédient | Application rate g a.i, / ha | Herbicidal action 28 DAT against Viola tricoior |
| A1 | 1 | 50 |
| (B2.37) Mesosulfuron | 15 | 80 |
| A1 + (B2.37) Mesosulfuron | 1 + 15 | EA = 97 (Ec = 90) Δ = 7 |
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Alopecurus myosuroides |
| Al | 1 | 15 |
| (B2.58) Propyzamide | 100 | 0 |
| A1 + (B2.58) Propyzamide | 1 + 100 | EA = 20 (Ec = 15) Δ = 5 |
| Active ingrédient | Application rate g a.i. ! ha | Herbicidal action 28 DAT against Bromus sterilis |
| A1 | 4 1 | 60 25 |
| (B2.58) Propyzamide | 900 300 | 30 15 |
| A1 + (B2.58) Propyzamide | 4 + 900 4 + 300 1 +900 | EA = 97 (Ec = 72) Δ = 25 EA = 85 (Ec=66) Δ = 19 EA = 70 (Ec = 48) Δ = 22 |
| Active ingrédient | Application rate g a.i. ! ha | Herbicidal action 28 DAT against Centaurea cyanus |
| A1 | 1 | 0 |
| (B2.58) Propyzamide | 900 100 | 15 10 |
| A1 + (B2.58) Propyzamide | 1 +900 1 + 100 | EA = 30 (Ec = 15) Δ = 15 EA= 15 (Ec = 10) Δ = 5 |
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Galium aparine |
| A1 | 16 | 80 |
| 1 | 20 | |
| (B2.58) Propyzamide | 300 | 20 |
| 900 | 20 | |
| 100 | 10 | |
| A1 + (B2.58) Propyzamide | 16 + 300 | EA = 93 (Ec =84) Δ = 9 |
| 1 +900 | EA = 93 (Ec = 36) Δ = 57 | |
| 1 +300 | EA = 80 (Ec = 36) Δ = 44 | |
| 1+100 | EA = 70 (Ec = 28) Δ = 42 |
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Matricaria inodora |
| A1 | 16 | 65 |
| 4 | 40 | |
| (B2.58) Propyzamide | 900 | 15 |
| 300 | 0 | |
| 100 | 0 | |
| A1 + (B2.58) Propyzamide | 16 + 900 | EA = 80 (Ec = 70) Δ = 10 |
| 16 + 300 | EA = 98 (Ec = 65) Δ = 33 | |
| 16 + 100 | EA = 80 (Ec = 65) Δ = 15 | |
| 4 + 900 | EA = 80 (Ec = 49) Δ = 31 | |
| 4 + 300 | EA = 85 (Ec = 40) Δ = 45 |
127 + 100 | EA - 60 (Ec = 40) Δ = 20
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Phalaris mînor |
| A1 | 4 1 | 65 25 |
| (B2.58) Propyzamîde | 300 900 | 20 30 |
| Al + (B2.58) Propyzamîde | 4 + 300 1 + 900 | Ea = 95 (Ec =72) Δ = 23 EA = 65 (Ec = 48) Δ = 17 |
| Active ingrédient | Application rate g a.i, / ha | Herbicidal action 28 DAT against Poa annua L. |
| A1 | 4 1 | 70 30 |
| (B2.58) Propyzamîde | 300 100 | 50 15 |
| A1 + (B2.58) Propyzamîde | 4 + 300 4+ 100 1 + 100 | EA = 98 (Ec = 85) Δ = 13 EA = 98 (Ec = 75) Δ = 23 EA = 65 (Ec = 41) Δ = 24 |
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Veronica hederifolia |
| A1 | 16 | 90 |
| 4 | 85 | |
| 1 | 15 | |
| (B2.58) Propyzamîde | 100 | 0 |
| 900 | 40 | |
| 300 | 80 | |
| A1 + (B2.58) Propyzamîde | 16+100 | EA = 95 (Ec = 90) Δ = 5 |
| 4+100 | EA=90 (Ec = 85) Δ = 5 | |
| 1 +900 | EA = 90 (EC = 49) Δ = 41 | |
| 1 + 300 | EA = 90 (Ec = 83) Δ = 7 | |
| 1+100 | EA = 30 (Ec = 15) Δ = 15 |
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Viola tricolor |
| A1 | 16 | 70 |
| 4 | 50 | |
| 1 | 15 | |
| (B2.58) | 900 | 0 |
| 300 | 20 | |
| A1 + (B2.58) Propyzamîde | 16 + 900 | EA = 95 (Ec = 70) Δ = 25 |
| 16 + 300 | EA = 95 (Ec = 76) Δ = 19 | |
| 4 + 900 | EA = 95 (Ec = 50) Δ = 45 | |
| 1 +900 | EA = 95 (Ec=15) Δ = 80 |
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Bromus sterilis |
| A1 | 4 1 | 60 25 |
| (B4.22) Pyrasulfotole | 45 15 | 20 10 |
| A1 + (B4.22) Pyrasulfotole | 4 + 45 | EA - 90 (Ec = 68) Δ = 22 |
128
| 4 + 15 | EA = 80 (Ec= 64) Δ = 16 | |
| 1 +45 | EA = 55 (Ec = 40) Δ=15 | |
| 1 + 15 | EA = 50 (Ec = 33) Δ= 17 |
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Centaurea cyanus |
| A1 | 4 | 15 |
| 1 | 0 | |
| (B4.22) Pyrasulfotole | 5 | 0 |
| 45 | 15 | |
| 15 | 10 | |
| A1 + (B4.22) Pyrasulfotole | 4 + 5 | EA = 25 (Ec = 15) Δ = 10 |
| 1 +45 | EA = 30 (Ec = 15) Δ = 15 | |
| 1 + 15 | EA = 15 (Ec = 10) Δ = 5 | |
| 1 + 5 | EA = 25 (Ec = 0) Δ = 25 |
| Active ingrédient | Application rate g a.i. ! ha | Herbicidal action 28 DAT against Galium aparine |
| A1 | 1 | 20 |
| (B4.22) Pyrasulfotole | 45 | 60 |
| 15 | 0 | |
| 5 | 0 | |
| A1 + (B4.22) Pyrasulfotole | 1 + 45 | EA = 95 (Ec = 68) Δ = 27 |
| 1 + 15 | EA = 40 (Ec = 20) Δ = 20 | |
| 1 + 5 | EA = 35 (Ec = 20) Δ = 15 |
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Lolium rigidum (résistant biotype) |
| A1 | 16 | 40 |
| (B4.22) Pyrasulfotole | 15 5 | 0 0 |
| A1 + (B4.22) Pyrasulfotole | 16 + 15 16 + 5 | EA = 50 (Ec = 40) Δ= 10 EA = 60 (Ec = 40) Δ = 20 |
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Matricaria inodora |
| A1 | 16 | 65 |
| 4 | 40 | |
| (B4.22) Pyrasulfotole | 45 | 15 |
| 15 | 0 | |
| 5 | 0 | |
| A1 + (B4.22) Pyrasulfotole | 16 + 45 | EA = 98 (Ec = 70) Δ = 28 |
| 16 + 15 | EA = 80 (Ec = 65) Δ = 15 | |
| 16 + 5 | EA = 80 (Ec = 65) Δ=15 | |
| 4 + 45 | EA = 80 (Ec = 49) Δ = 31 | |
| 4 + 15 | EA = 70 (Ec = 40) Δ = 30 | |
| 4 + 5 | EA = 50 (Ec = 40) Δ = 10 |
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Phalaris minor |
| A1 | 4 1 | 65 25 |
| (B4.22) Pyrasulfotole | 5 | 0 |
| A1 + (B4.22) Pyrasulfotole | 4 + 5 | EA = 70 (Ec = 65) Δ = 5 |
129 +5
EA = 30 (Ec = 25) Δ = 5
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Poa annua L. |
| A1 | 4 | 70 |
| (B4.22) Pyrasulfotole | 15 5 | 0 0 |
| A1 + (B4.22) Pyrasulfotole | 4+15 4 + 5 | EA = 80 (EC = 70) Δ = 10 EA = 97 (Ec = 70) Δ = 27 |
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Veronica hederifolia |
| A1 | 1 | 15 |
| (B4.22) Pyrasulfotole | 45 5 | 65 10 |
| A1 + (B4.22) Pyrasulfotole | 1 + 45 1 + 5 | EA = 97 (Ec = 70) Δ = 27 EA = 70 (Ec = 24) Δ = 46 |
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Alopecurus myosuroides |
| A1 | 1 | 15 |
| (B2.68) Thiencarbazone [CAS 317815-83-1] | 1.5 | 40 |
| A1 + (B2.68) Thiencarbazone [CAS 317815-83-1] | 1+1.5 | EA = 65 (Ec = 49) Δ= 16 |
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Bromus sterilîs |
| A1 | 4 | 60 |
| 1 | 25 ____ | |
| (B2.68) Thiencarbazone [CAS | 1.5 | 25 |
| 317815-83-1] | ||
| 0.5 | 20 ___ | |
| A1 + (B2.68) Thiencarbazone [CAS 317815-83-1] | 4+1.5 | EA = 90 (Ec = 70) Δ = 20 |
| 4 + 0.5 | EA = 90 (Ec = 68) Δ = 22 | |
| 1 +0.5 | EA = 70 (Ec = 40) Δ = 30 |
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Centaures cyanus |
| A1 | 4 | 15 |
| 1 | 0 | |
| (B2.68) Thiencarbazone [CAS | 0.5 | 10 |
| 317815-83-1] | ||
| 1.5 | 20 | |
| 0.17 | 15 | |
| A1 + (B2.68) Thiencarbazone | 4 + 0.5 | EA = 30 (Ec = 24) Δ = 6 |
| [CAS 317815-83-1] | 1+1.5 | EA = 35 (Ec = 20) Δ = 15 |
| 1 + 0.5 | EA = 25 (Ec =10) Δ = 15 | |
| 1 + 0.17 | EA = 20(Ec=15) Δ = 5 |
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Galium aparine |
130
| A1 | 1 | 20 |
| (B2.68) Thiencarbazone [CAS | 1.5 | 35 |
| 317815-83-1] | ||
| 0.5 | 0 | |
| 0.17 | 30 | |
| A1 + (B2.68) Thiencarbazone | 1+1.5 | EA = 75 (Ec = 48) Δ = 27 |
| [CAS 317815-83-1] | ||
| 1 +0.5 | EA = 25 (Ec = 20) Δ = 5 | |
| 1 +0.17 | EA = 50 (Ec = 44) Δ = 6 |
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Lolium rigidum (résistant biotype) |
| A1 | 16 | 40 |
| (B2.68) Thiencarbazone [CAS 317815-83-11 | 0.17 | 10 |
| A1 + (B2.68) Thiencarbazone [CAS 317815-83-11 | 16 + 0.17 | EA = 65 (Ec = 46) Δ = 19 |
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Matricaria inodora |
| A1 | 4 | 40 |
| (B2.68) Thiencarbazone [CAS 317815-83-11 | 0.5 | 30 |
| A1 + (B2.68) Thiencarbazone [CAS 317815-83-11 | 4 + 0.5 | EA = 80 (Ec = 58) Δ = 22 |
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Phalaris minor |
| A1 | 4 | 65__ |
| (B2.68) Thiencarbazone [CAS 317815-83-1] | 0.5 | 25 |
| A1 + (B2.68) Thiencarbazone [CAS 317815-83-11 | 4 + 0.5 | EA = 97 (Ec = 74) Δ = 23 |
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Poa annua L. ____ |
| Al | 4 | 70 |
| (B2.68) Thiencarbazone [CAS 317815-83-11 | 0.5 | 25 |
| Al + (B2.68) Thiencarbazone [CAS 317815-83-11 | 4 + 0.5 | EA = 98 (Ec = 78) Δ = 20 |
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Veronica hederifolia __ |
| A1 | 1 | 15 |
| (B2.68) Thiencarbazone [CAS 317815-83-1] | 0.5 | 40 |
| Al + (B2.68) Thiencarbazone [CAS 317815-83-11 | 1 + 0.5 | EA = 65 (Ec = 49) Δ = 16 |
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Viola tricolor |
| A1 | 4 1 | 50 15 |
131
| (B2.68) Thiencarbazotie [CAS 317815-83-1] | 1.5 | 20 |
| A1 + (B2.68) Thiencarbazone [CAS 317815-83-1] | 4+1.5 1 + 1.5 | EA = 95 (Ec = 60) Δ = 35 EA = 80 (Ec = 32) Δ = 48 |
Table 3.4; Synergistic effect (Δ) for herbicidal binary compositions comprising herbicide A8, applied by the post-emergence method
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Alopecurus myosuroides |
| A8 | 16 | 80 |
| 4 | 35 | |
| (B2.18) Diflufenican | 270 | 30 |
| 90 | 15 | |
| 30 | 10 | |
| A8 + (B2.18) Diflufenican | 16 + 270 | EA = 93 (Ec = 86) Δ = 7 |
| 16 + 90 | EA = 95 (Ec = 83) Δ = 12 | |
| 4 + 30 | Ea = 50 (Ec = 42) Δ = 8 |
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Bromus sterilis |
| A8 | 4 | 35 |
| (B2.18) Diflufenican | 270 | 20 |
| 90 | 15 | |
| 30 | 0 | |
| A8 + (B2.18) Diflufenican | 4 + 270 | Ea = 80 (Ec = 48) Δ = 32 |
| 4 + 90 | EA = 95 (Ec = 45) Δ = 50 | |
| 4 + 30_______ | EA - 60 (Ec = 35) Δ = 25 |
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Galium aparine |
| A8 | 1 | 25 |
| (B2.18) Diflufenican | 270 | 60 __ |
| A8 + (B2.18) Diflufenican | 1 + 270 | EA = 75 (Ec = 70) Δ = 5 |
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Lamium purpureum L. |
| A8 | 16 | 80 |
| 4 | 50 | |
| (B2.18) Diflufenican | 270 | 20 |
| 90 | 20 | |
| A8 + (B2.18) Diflufenican | 16 + 270 | EA = 97 (Ec = 84) Δ = 13 |
| 16 + 90 | EA = 98 (EC = 84M = 14 | |
| 4 + 270 | EA = 100 (Ec = 60) Δ = 40 | |
| 4 + 90 | EA = 97 (Ec = 60) Δ = 37 |
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Lolium rigidum |
| A8 | 16 | 40 |
| (B2.18) Diflufenican | 270 | 20 |
132
| 90 30 | 10 0 | |
| A8 + (B2.18) Diflufenican | 16 + 270 | Ea = 60 (Ec = 52)Δ = 8 |
| 16 + 90 | EA = 80 (Ec = 46) Δ = 34 | |
| 16 + 30 | Ea = 60 (Ec = 40) Δ = 20 |
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Lolium rigidum (résistant biotype) |
| A8 | 4 | 20 |
| (B2.18) Diflufenican | 30 | 0 |
| A8 + (B2.18) Diflufenican | 4 + 30 | EA = 25 (Ec = 20) Δ = 5 |
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Matricaria inodora |
| A8 | 16 4 | 80 40 |
| (B2.18) Diflufenican | 270 90 | 15 15 |
| A8 + (B2.18) Diflufenican | 16 + 270 16 + 90 4 + 270 | Ea = 98 (Ec = 83) Δ = 15 EA = 97 (Ε° = 83)Δ=14 EA = 85 (Ec = 49) Δ = 36 |
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Phalaris minor _____ |
| A8 | 16 1 | 60 0 |
| (B2.18) Diflufenican | 30 | 10 |
| A8 + (B2.18) Diflufenican | 16 + 30 1 + 30_______ | Ea = 80 (Ec = 64) Δ = 16 EA = 15 (Ec = 10) Δ = 5 |
| Active ingrédient | Application rate g a.i. ! ha | Herbicidal action 28 DAT against Poa annua L. |
| A8 | 16 | 40 |
| 4 | 20 | |
| (B2.18) Diflufenican | 270 | 25 |
| 90 | 20 | |
| 30 | 0 | |
| A8 + (B2.18) Diflufenican | 16 + 270 | EA = 70 (Ec = 55) Δ = 15 |
| 16 + 90 | EA = 65 (EC = 52)A = 13 | |
| 16 + 30 | EA = 93 (Ec = 40) Δ = 53 | |
| 4 + 270 | EA = 90 (Ec = 40) Δ = 50 | |
| 4 + 90 | EA = 65 (Ec = 36) Δ = 29 | |
| 4 + 30______ | EA = 85 (Ec = 20) Δ = 65 |
| Active ingrédient | Application rate g a.i. ! ha | Herbicidal action 28 DAT against Véron ica hederifolia ______ |
| A8 | 16 | 35 |
| 4 | 80 | |
| (B2.18) Diflufenican | 270 | 40 |
| 90 | 20 | |
| 30 | 40 | |
| A3 + (B2.18) Diflufenican | 16 + 270 | EA = 98 (Ec = 61) Δ = 37 |
| 16 + 90 | EA = 65 (Ec = 48) Δ = 17 | |
| 16 + 30 | EA = 97 (Ec = 61)Δ = 36 |
133
| 4 + 270 | EA = 97 (Ec = 88) Δ = 9 | |
| 4 + 30 | EA = 97 (Ec = 88) Δ = 9 |
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Viola tricolor |
| A8 | 4 | 0 |
| 1 | 20 | |
| (B2.18) Diflufenican | 90 | 75 |
| 30 | 65 | |
| A8 + (B2.18) Diflufenican | 4 + 90 | EA - 100 (Ec = 75) Δ = 25 |
| 4 + 30 | EA = 100 (Ec = 65) Δ = 35 | |
| 1 +90 | EA=100 (Ec = 80) Δ = 20 | |
| 1 + 30 | EA= 100 (Ec = 72) Δ = 28 |
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Alopecurus myosuroides |
| A8 | 16 | 80 |
| (B7.4) Glufosinate [CAS 7718282-2] | 540 60 | 40 15 |
| A8 + (B7.4) Glufosinate [CAS 77182-82-2] | 16 + 540 16 + 60 | EA = 97 (Ec = 88) Δ = 9 EA = 93 (Ec = 83) Δ = 10 |
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Bromus sterilis |
| A8 | 4 | 35 |
| (B7.4) Glufosinate [CAS 7718282-2] | 540 | 35 |
| 180 | 25 | |
| 60 | 0 | |
| A8 + (B7.4) Glufosinate [CAS 77182-82-2] | 4 + 540 | Ea = 95 (EC = 58) Δ = 37 |
| 4 + 180 | EA = 65 (Ec = 51) Δ = 14 | |
| 4 + 60_______ | EA = 70 (Ec = 35) Δ = 35 |
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Lamium purpureum L.____ |
| A8 | 16 4 | 80 50 |
| (B7.4) Glufosinate [CAS 7718282-2] | 60 | 0 |
| A8 + (B7.4) Glufosinate [CAS 77182-82-2] | 16 + 60 4 + 60 | EA = 98 (Ec = 80) Δ = 18 Ea = 70 (Ec = 50) Δ = 20 |
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Lolium rigidum |
| A8 | 16 4 | 40 20 |
| (B7.4) Glufosinate [CAS 7718282-2] | 540 180 | 30 10 |
134
| • | A8 + (B7.4) Glufosinate [CAS 77182-82-2] | 16 + 540 16 + 180 4 + 540 4+180 | ΕΛ - 98 (Ec = 58) Δ = 40 EA = 70 (Ec = 46) Δ = 24 EA = 50 (Ec = 44) Δ = 6 Ea = 50 (Ec = 28) Δ = 22 |
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Phalaris minor |
| A8 | 16 | 60 |
| (B7.4) Glufosinate [CAS 7718282-2] | 540 | 25 |
| 180 | 15 | |
| 60 | 0 | |
| A8 + (B7.4) Glufosinate [CAS 77182-82-2] | 16 + 540 | EA = 97 (Ec = 70) Δ = 27 |
| 16 + 180 | EA = 80 (Ec = 66) Δ = 14 | |
| 16 + 60 | EA = 80 (Ec = 60) Δ = 20 |
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Poa annua L. |
| A8 | 16 | 40 |
| 4 | 20 | |
| 1 | 20 | |
| (B7.4) Glufosinate [CAS 77182- | 540 | 15 |
| 82-2] | ||
| 180 | 0 | |
| 60 | 0 | |
| A8 + (B7,4) Glufosinate [CAS 77182-82-2] | 16 + 540 | EA = 97 (Ec = 49) Δ = 48 |
| 16 + 180 | EA = 90 (Ec = 40) Δ = 50 | |
| 4 + 540 | EA = 100 (Ec = 32) Δ = 68 | |
| 4+180 | EA = 95 (Ec = 20) Δ = 75 | |
| 4 + 60 | EA = 30 (Ec = 20) Δ = 10 | |
| 1 + 540 | EA = 40 (Ec = 32) Δ = 8 |
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Veronica hederifolia |
| A8 | 16 | 35 |
| 1 | 20 __ | |
| (B7.4) Glufosinate [CAS 77182- | 540 | 90 |
| 82-2] | ||
| 60 | 40 | |
| 180 | 70 _____ | |
| A8 + (B7.4) Glufosinate [CAS | 16 + 540 | EA = 100 (Ec = 94) Δ = 6 |
| 77182-82-2] | ||
| 16 + 60 | EA = 70 (Ec = 61) Δ = 9 | |
| 1 + 540 | EA = 100 (Ec = 92) Δ = 8 | |
| 1+180 | EA = 95 (Ec = 76) Δ = 19 |
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Viola tricolor |
| A8 | 4 | 0 |
| (B7.4) Glufosinate [CAS 7718282-2] | 60 | 10 |
135
| A3 + (B7.4) Glufosinate [CAS 77182-82-21 | 4 + 60 | EA = 50 (Ε°=10)Δ = 40 |
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Alopecurus myosuroides |
| A8 | 16 | 80 |
| (B7.5) Glyphosate [CAS 38641-94-0] | 150 | 25 |
| A8 + (B7.5) Glyphosate [CAS 38641-94-0] | 16+150 | EA = 93 (Ec = 85) Δ = 8 |
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Bromus sterilis |
| A8 | 4 | 35 |
| 1 | 15 | |
| (B7.5) Glyphosate | 450 | 50 |
| [CAS 38641-94-0] | ||
| 150 | 20 | |
| 50 | 0 | |
| A8 + (B7.5) Glyphosate | 4 + 450 | Ea = 98 (Ec = 68) Δ = 30 |
| [CAS 38641-94-01 | ||
| 4+150 | EA = 95 (Ec = 48) Δ = 47 | |
| 4 + 50 | EA = 65 (Ec = 35) Δ = 30 | |
| 1 + 50 | EA = 20 (Ec = 15) Δ = 5 |
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Centau rea cyanus__ |
| A3 | 1 | 30 ___ |
| (B7.5) Glyphosate [CAS 38641-94-0] | 450 | 65 |
| A8 + (B7.5) Glyphosate [CAS 38641-94-01 | 1 +450 | EA = 97 (Ec = 76) Δ = 21 |
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Galium aparine |
| A3 | 1 | 25 |
| (B7.5) Glyphosate [CAS 38641-94-0] | 450 | 40 |
| A3 + (B7.5) Glyphosate [CAS 38641-94-01 | 1 +450 | EA = 60 (Ec = 55) Δ = 5 |
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Lolium rigidum ____ |
| A8 | 16 | 40 |
| 4 | 20 | |
| (B7.5) Glyphosate | 450 | 35 |
| [CAS 38641-94-0] | ||
| 150 | 30 | |
| 50 | 0 | |
| A3 + (B7.5) Glyphosate | 16 + 450 | EA = 70 (Ε° = 61)Δ = 9 |
| [CAS 38641-94-0] | ||
| 16 + 150 | EA = 85 (Ec = 58) Δ = 27 | |
| 16 + 50 | EA = 70 (Ec = 40) Δ = 30 | |
| 4 + 450 | EA = 60 (Ε° = 48)Δ = 12 |
136 + 50 I EA = 25 (Ec = 20)Δ = 5
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Matricaria inodora |
| A8 | 16 | 80 |
| 4 | 40 | |
| 1 | 35 | |
| (B7.5) Glyphosate [CAS 38641-94-01 | 450 | 20 |
| 50 | 0 | |
| 150 | 0 | |
| A8 + (B7.5) Glyphosate [CAS 38641-94-01 | 16 + 450 | EA = 95 (Ec = 84)Δ = 11 |
| 4 + 450 | ΕΛ = 70 (Ec = 52)Δ= 18 | |
| 4 + 50 | Ea = 65 (Ec = 40) Δ = 25 | |
| 1 + 150 | EA = 70 (Ec = 35) Δ = 35 | |
| 1 + 50 | Ea = 40 (Ec = 35) Δ = 5 |
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Phalaris minor |
| A8 | 16 | 60 |
| 1 | 0 __ | |
| (B7.5) Glyphosate [CAS 38641-94-01 | 450 | 20 |
| 150 | 10 | |
| 50 | 0 ___ | |
| A8 + (B7.5) Glyphosate [CAS 38641-94-01 | 16 + 450 | EA = 75 (Ec = 68) Δ = 7 |
| 16+150 | Ea = 75 (Ec = 64) Δ = 11 | |
| 16 + 50 | EA = 80 (Ec = 60) Δ = 20 | |
| 1 + 450 | EA = 25 (Ec = 20) Δ = 5 |
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Poa annua L. ____ |
| A8 | 16 | 40 |
| 4 | 20 | |
| 1 | 20 __ | |
| (B7.5) Glyphosate [CAS 38641-94-01 | 50 | 0 |
| 450 | 40 | |
| 150 | 40 | |
| A8 + (B7.5) Glyphosate [CAS 38641-94-01 | 16 + 50 | EA = 56 (Ec = 40) Δ = 16 |
| 4 + 450 | EA = 65 (Ec = 52) Δ = 13 | |
| 4+150 | Ea = 80 (Ec = 52) Δ = 28 | |
| 4 + 50 | EA = 40 (Ec = 20) Δ = 20 | |
| 1 + 450 | EA = 60 (Ec = 52) Δ = 8 |
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Veronica hederifoiia |
| A8 | 16 1 | 35 20 |
| (B7.5) Glyphosate [CAS 38641-94-01 | 450 50 | 60 15 |
137
| A8 + (B7.5) Glyphosate [CAS 38641-94-0] | 16 + 450 16 + 50 1 + 450 1 + 50 | EA = 90 (Ε° = 74)Δ = 16 EA - 60 (Ec = 45) Δ = 15 Ea = 95 (Ec = 68) Δ = 27 EA = 90 (Ec = 32) Δ = 58 |
| Active ingrédient | Application rate g a.i. / ha | Herbicidal action 28 DAT against Viola tricolor |
| A8 | 16 | 15 |
| 4 | 0 | |
| 1 | 20 | |
| (B7.5) Glyphosate [CAS 38641-94-0] | 450 | 10 |
| 150 | 0 | |
| 50 | 0 | |
| A8 + (B7.5) Glyphosate [CAS 38641-94-0] | 16 + 450 | EA = 50 (Ec = 24) Δ = 26 |
| 16 + 150 | EA = 20 (Ec = 15) Δ = 5 | |
| 16 + 50 | EA = 20 (Ec = 15) Δ= 5 | |
| 4 + 450 | EA = 40 (Ec = 10) Δ = 30 | |
| 4 + 150 | Ea - 30 (Ec = 0) Δ = 30 | |
| 4 + 50 | EA = 15 (Ec = 0) Δ = 15 | |
| 1 + 450 | Ea = 60 (Ec = 28) Δ = 32 | |
| 1 + 50 | EA = 30 (Ec= 20) Δ = 10 |
138
Claims (19)
- Compositions comprising herbicidally active compounds (A) and (B), wherein (A) represents one or more compounds of the general formula (I) or agrochemicaily acceptable salts thereof [herbicides (A)], în whichG dénotés a group of the formula OR4 or NRUR12;R1 and R2 are each independently hydrogen, halogen or cyano, or are (Ci-Cjj-alkyl or (Ci-CQ-alkoxy, each substîtuted by m radicals from the group consisting of halogen and cyano;R3 is cyano or fluorine, or is (Ci-C5)-aikyl, (C3-C6)-cycloalkyl, (C2-C5)-alkenyl, (C2-C5)-alkynyI or (C1-C5)alkoxy, each substîtuted by m radicals from the group consisting of halogen, cyano, (CrCj)-alkoxy and hydroxy;R4 is hydrogen, or is (Cj-C12)-alkyl, (C3-C7)-cycloalkyl, (C3-C7)-cycloalkyl-(Ci-C8)-alkyl, (C2-C8)-alkenyl, (Cs-CQ-cycloalkenyl or (C2-C8)-alkynyi, each substîtuted by m radicals from the group consisting of halogen, cyano, (Ci-CQ-alkoxy, hydroxy and aryl;Y is oxygen or sulfur;W is oxygen or sulfur;139Z represents a monounsaturated cyclopentane ring substituted by k radicals trom the group of Rin, (R10)kZ where the arrow in each case represents a bond to the group C=W of the formula (I);Rlü is halogen, cyano or CO2R7, or is (Ci-C2)-alkyl or (Ci-Cjj-alkoxy, each substituted by m radicals from the group consisting of fluorine and chlorine;R11, R12 are each independentiy hydrogen, cyano, OR7, S(O)nR5, SOtNR6R7, CO2R8, CONR6R8, COR6, NRÛR8, NR6COR8, NR6CONR8R8, NR6CO2R8, NR6SO2R8, NRf’SO2NR6R8, C(Rfi)=NOR8, optionally substituted aryl, optionally substituted heteroaryl or optionally substituted heterocyclyl, or are (Ci-Ci2)-alkyl, (C3-C8)-cycloalkyl, (C3-C7)-cycloalkyl-(Ci-C7)-alkyl, (C2Ci2)-alkenyl, (C5-C7)-cycloalkenyl or (C2-Ct2)-alkynyl, each substituted by m radicals from the group consisting of halogen, cyano, nîtro, OR7, S(O)nR5, SO2NR6R7, CO2Rs, CONR6R8, COR6, NR6R8, NR6COR8, NR6CONR8R8, NR6CO2R8, NR6SO2R8, NR6SO2NR6R8, C(R6)=NOR8, optionally substituted aryl, optionally substituted heteroaryl and optionally substituted heterocyclyl, orR11 and R12 together with the nitrogen atom to which they are bonded form a saturated or partly or fully unsaturated five-, six- or seven-membered ring which is optionally mono- to hexasubstituted by radicals from the group consisting of halogen, cyano, nitro, (Ci-C/J-alkyl, halo-(Ci-Q,)-alkyl, oxo, OR7, S(O),iR5, SO2NR6R7, CO2R8, CONR6R8, COR6, NR6R8, NR6COR8, NR6CONR8R8, NR6CO2R8, NRfiSO2R8, NR6SO2NR6Rk and C(R6)=NOR8 and which, in addition to that nitrogen atom, contains r carbon atoms, o oxygen atoms, p sulfur atoms and q éléments from the group consisting of NR7 and NCOR7 as ring atoms;140B X2, X4 and Χΰ are each independently hydrogen, halogen or cyano, or are (Ci-C2)-alkyl, in each case substituted by m radicals from the group consisting of fluorine, chlorine, bromine and (Cj-C2)-alkoxy;X3 and X5 are each independently hydrogen, fluorine, chlorine, bromine, iodine, hydroxy, cyano, nitro, 3(01,R6 or CO2R7, or are (Ci-C3)-alkyl, (Ci-C3)-alkoxy, (C3-C4)-cycloalkyi, (C2-C3)-alkenyl or (C210 C3)-alkynyl, each substituted by m radicals from the group consisting of fluorine, chlorine and bromine;R5 is (Ci-CQ-alkyl, (Ca-CQ-cycloalkyl or aryl, each substituted by m radicals from the group consisting of halogen, cyano and hydroxy;R6 is hydrogen or R3;R7 is hydrogen, or20 is (Ci-C6)-alkyl, (C3-C6)-cycloaIkyl, (C3-C4)-alkenyl or (C3-C4)-alkynyl, each substituted by m radicals from the group consisting of halogen, cyano and (Ci-C2)alkoxy;Rs is hydrogen,25 or is (Ci-C8)-alkyl, (C3-C6)-cycIoaIkyi, (C3-Cs)-alkenyl or (C3-C8)-alkynyl, each substituted by m radicals from the group consisting of halogen, cyano and (Ci-C2)alkoxy;30 the index k îs 0, 1 or 2; where, when k > 1, R1(1 may independently be the same or different;the index m is 0,1, 2, 3, 4 or 5;the index n is 0, 1 or 2;the index o is 0, 1 or 2;141 the index p is 0 or 1;the index q is 0 or 1; and5 the index r is 3, 4, 5 or 6;and (B) represents one or more herbicides [component (B)] from the group of the active herbicidal ingrédients (Bl) to (Bll), in which (Bl) represents active herbicidal ingrédients from the group of the 1,3-diketo compounds selected from (Bl.l) alloxydim.(B1.2) bicyclopyrone, (B1.3) butroxydim, (B1.4) clethodim.(B1.5) cycloxydim, (B1.6) fenquinotrione.(B1.7) mesotrione, (B1.8) pinoxaden, (B1.9) profoxydim, (B 1.10) sethoxydim, (Bl.ll) sulcotrione, (Bl.l 2) SYP-9121 (B1.13) tefuryltrione, (B1.14) tembotrione, (B1.15) tepraloxydim, (B1.16) traJkoxydim, (B1.17) Y13161, (B1.18) Y13287;15 (B2) represents active herbicidal ingrédients from the group of the (sulfon)amides selected from (B2.1) acetochlor.(B2.2) alachlor, (B2.3) (B2.4) amidosulfuron, asulam,142 (B2.5) (B2.6) azimsulfuron, beflubutamid, (B2.7) bensulfuron.(B2.8) (B2.9) (B2.10) (B2.ll) (B2.12) (B2.13) (B2.14) (B2.15) (B2.16) (B2.17) (B2.18) (B2.19) (B2.20) (B2.21) (B2.22) (B2.23) (B2.24) (B2.25) (B2.26) (B2.27) (B2.28) (B2.29) (B2.30) (B2.31) (B2.32) (B2.33) (B2.34) (B2.35) (B2.36) (B2.37) (B2.38) (B2.39) (B2.40) (B2.41) butachlor, carbetamide, chloritnuron, chlorpropham, chlorsulfuron, cinosulfuron, cloransulam, cyclosulfamuron, desmedipham, diclosulam, diflufenican, dîmethachlor, dimethenamid, esprocarb, ethametsulfuron, ethoxysulfuron, flazasulfuron, florasulam, flucarbazone, flucetosulfuron, flufenacet, flumetsulam, flupyrsidfuron, foramsulfuron, halosulfuron, imazosulfuron, îodosulfuron, ipfencarbazone, mefenacet, niesosulfuron, metazachlor, metazosulfuron, metolachlor, metosulam,143(BZ42) metsulfuron.(B2.43) nicosulfuron, (B2.44) orthosulfamuron, (B2.45) oxasulfuron.(B2.46) penoxsulam, (B2.47) pethoxamide.(B2.48) phenmedipham, (B2.49) picolinafen, (B2.50) pretilachlor, (B2.51) prîmisulfuron, (B2.52) propachlor.(B2.53) propanil, (B2.54) propham;(B2.55) propisochlor, (B2.56) propoxycarbazone, (B2.57) propyrisulfuron, (B2.58) propyzamide, (B2.59) prosulfocarb, (B2.60) prosulfuron, (B2.61) pyrazosulfuron, (B2.62) pyroxsulam, (B2.63) rimsulfuron.(B2.64) S~metolachlor, (B2.65) sulfometuron.(B2.66) sulfosulfuron, (B2.67) thenylchlor.(B2.68) thiencarbazone.(B2.69) thifensulfuron, (B2.70) tri-allate, (B2.71) trîasulfuron.(B2.72) tribenuron, (B2.73) trifloxysulfuron, (B2.74) triflusulfuron, (B2.75) tritosulfuron.(B2.76) esprocarb.(B2.77) profluazol, (B2.78) tri-allate;144(B3) represents active herbicidal ingrédients from the group of the aryl nitriles selected from (Β3Λ) bromoxynil, (B3.2) chlorthîamid, (B3.3) dichlobenil, (B3.4) ioxynil, (B3.5) pyraclonil;(B4) represents active herbicidal ingrédients from the group of the azoles selected from (B4.1) amicarbazone.(B4.2) amitrole, (B4.3) azafenidin, (B4.4) benzofenap, (B4.5) be n z uofu cao to n g, (B4.6) bîscarfentrazone, (B4.7) café nst rôle, (B4.8) carfentrazone, (B4.9) fentrazamide, (B4.10) imazamethabenz, (B4.ll) imazamox, (B4.12) imazapic, (B4.13) imazapyr.(B4.14) imazaquin, (B4.15) imazethapyr, (B4.16) isouron, (B4.17) isoxaben, (B4.18) isox afin tôle.(B4.19) oxadiargyl, (B4.20) oxadiazon, (B4.21) pyraflufen, (B4.22) pyrasulfotole, (B4.23) pyrazolynate, (B4.24) pyrazoxyfen, (B4.25) pyroxasulfone, (B4.26) sulfentrazone.(B4.27) tolpyralate, (B4.28) topramezone.145(B4.29) triazolesulcotrione (QYR-301), (B4.30) QYM-201;(B4.31) bencarbazone, (B4.32) fluazolate, (B4.33) flupoxam, (B4.34) isoxachlortole;(B5) represents further active herbicidal ingrédients selected from (B5.1) aminocyclopyrachlor.(B5.2) aminopyralid, (B5.3) benazolin-ethyl.(B5.4) benfluralin, (B5.5) bentazone, (B5.6) benzobicyclon.(B5.8) bromofenoxim.(B5.9) butralin, (B5.10) chloridazon/pyrazon, (B5.ll) chlorthal, (B5.12) cinidon-ethyl, (B5.13) cinmethylin.(B5.14) clomazone, (B5.15) cyclopyrimorate, (B5.16) dinitramine, (B5.17) diquat, (B5.18) dithiopyr, (B5.19) acetic acid.(B5.20) ethalfluralin, (B5.21) ethofumesate, (B5.22) flamprop, (B5.23) florpyrauxifen, (B5.24) flufenpyr.(B5.25) flumiclorac, (B5.26) flumioxazin, (B5.27) fluridone, (B5.28) flurochloridone.(B5.29) flurtamone, (B5.30) flut hiacet-met hyl,14« (B5.31) (B5.32) (B5.33) (B5.34) (B5.35) (B5.36) (B5.37) (B5.38) (B5.39) (B5.40) (B5.41) (B5.42) (B5.43) (B5.44) (B5.45) (B5.46) (B5.47) halauxifen, indanofan, norflurazon, oleic acid, oryzalin, oxaziclomefone, paraquat, pelargonic acid, pendimethalin, pentoxazone, pyridafol, pyridate, tetflupyrolimet, thiazopyr, triafamone, trifluralin; 4-amino-3-chloro-5-fluoro-6-(7fluoro-lH-indol-6-yl)pyridine-2carboxylic acid, (B5.48) (B5.49) (B5.5O) (B5.51) (B5.52) (B5.53) cyclopyrimorate, diquat, oxaziclomefone, pentanochlor, tebutam, thidiazimin;(B6) represents active herbicidal ingrédients from the group of the (het)arylcarboxylic acids selected from (B6.1) chloramben.(B6.2) clopyralid.(B6.3) dicamba, (B6.4) fluroxypyr, (B6.5) picloram, (B6.6) quinclorac.(B6.7) quinmerac, (B6.8) TB A, (B6.9) trichiopyr;147(B7) represents active herbicidal ingrédients from the group of the organic phosphorus compounds selected from (B7.1) anilofos, (B7.2) bialaphos, (B7.3) butamifos, (B7.4) glufosinate, (B7.5) glyphosate, (B7.6) piperophos.(B7.7) sulfosate, (B7.8) amiprofos;5 (B8) represents active herbicidal ingrédients from the group of the phenyl ethers selected from (B8.1) 2,4-D, (B8.2) 2,4-DB, (B8.3) 2,4-DP, (B8.4) acifluorfen, (B8.5) aclonifen, (B8.6) bifenox, (B8.7) chlomethoxyfen.(B8.8) clodinafop-propargyl, (B8.9) clomeprop.(B8.10) cyhalofop.(B8.ll) diclofop.(B8.12) ethoxyfen, (B8.13) fenoxaprop.(B8.14) fluazifop, (B8.15) fluoroglycofen, (B8.16) fomesafen, (B8.17) halosafen.(B8.18) haloxyfop, (B8.19) lactofen, (B8.20) MCP A, (B8.21) MCPB, (B8.22) mecoprop, (B8.23) metamifop, (B8.24) oxyfluorfen,148(B8.25) propaquizafop.(B8.26) quizalofop.(B8.27) quizaiofop-p, (B8.28) benzfendizone;(B9) represents active herbicidal ingrédients from the group of the pyrimidines selected from (B9.1) bispyrac-sodium, (B9.2) bromacil.(B9.3) butafenacil, (B9.4) lenacil, (B9.5) pyribenzoxim, (B9.6) pyriftalid.(B9.7) pyriminobac, (B9.8) pyrimisulfan.(B9.9) py ritiiiobac-sodi um, (B9.10) saflufenacil, (B9.ll) terbacii, (B9.12) tiafenacil.(B9.13) trifludîmoxazin;(B9.14) ethyl [3- [2-ch loro-4-fluoro-5-( 1 methy 1-6-trifluoromethy 1-2,4dioxo-l,2,3,4-tetrahydropyrimidin3-yl)phenoxy]-2- py ri d y lox y ] acet ate ;(B 10) represents active herbicidal ingrédients from the group of the (thio)ureas selected from (B10.1) (B 10.2) (B10.3) chlorobromuron, chlorotoluron, daimuron, (B10.4) (B10.5) (B10.6) (B 10.7) (B10.8) (B10.9) (B10.10) (B10.il) dimefuron, diuron, diflufenzopyr, fluometuron, isoproturon, linuron, methabenzthiazuron, metobromuron,149 (B 10.12) metoxuron, (B10.13) monolinuron.(B10.14) neburon, (B10.15) siduron, (B10.16) tebuthiuron.(B 10.17) fenuron, (B10.18) chloroxuron, (B10.19) diflufenzopyr, (B10.20) ethidimuron;(Bll) represents active herbicidal ingrédients from the group of the triazines selected from (Bll.l) ametryne, (B 11.2) atrazine, (Bll.3) cynazine, (B11.4) dimethametryn.(B11.5) hexazinone.(Bll .6) indaziflam.(B11.7) metamitron, (Bll.8) metribuzin, (B11.9) prometon.(B11.10) prometryne, (Bll.11) propazine, (Bll.12) simazine.(Bll. 13) simetryne, (Bll.14) terbumeton.(B11.15) terbuthylazîne, (B 11.16) terbutryne.(Bll. 17) triaziflam, (Bll.18) trietazine.(B 11.19) desmetryne.
- 2. Composition according to Claim 1, wherein comportent (A) of the general formula (I) is defined as follows:G dénotés a group of the formula OR4;150R1 and R2 are each hydrogen;R3 is (Ci-C3)-alkyl, (C3-C4)-cycloalkyl, (C2-C3)-alkenyI or (Ci-C3)-alkoxy, each substituted by m radicals from the group consisting of fluorine, chlorine and (Ci-Cïj-alkoxy;R4 is hydrogen, or (Ci-C3)-alkyl or (C2-C4)-alkenyl, each substituted by m radicals from the group consisting of fluorine, chlorine and (Ci-Czj-alkoxy;Y is oxygen;W is oxygen;Z represents a group Z-l, Z-4 or Z-6:y-C^-- y-O^ y^S^ 21 Z-4 Z-6 where the arrow in each case represents a bond to the group C=W of the formula (I);X2, X4 and X6 are each independently hydrogen or fluorine;X3 and X5 are each independently hydrogen, fluorine, cyano or methyl; and m is the index 0, 1, 2 or 3.
- 3. Composition according to Claim 1, wherein component (A) of the general formula (I) is defined as follows:G is a group of the formula NRHR12;R1 and R2 are each hydrogen;R3 is (Ci-C3)-alkyl, (C3-C4)-cycloalkyl, (Cz-C3)-alkenyl or (Ci-C3)-alkoxy, each substituted by m radicals from the group consisting of fluorine, chlorine and (Ci-Cjj-alkoxy;Y is oxygen;151W is oxygen;Z is a Z-l, Z-4 or Z-6 group:Z-1Z-4Z-65 where the arrow in each case represents a bond to the group C=W of the formula (I);X2, X4 and X6 are each independently hydrogen or fluorine;X3 and X5 are each independently hydrogen, fluorine, cyano or methyi;R5 is (Ci-Cej-alkyl or (Gi-CO-cycloaikyl, each substituted by m radicals from the group consisting of fluorine and chlorine;R6 is hydrogen or R5;R7 is hydrogen, or (CrCiQ-alkyl or (C3-Cfi)-cycloalkyl, each substituted by m radicals from the group consisting of fluorine, chlorine and (Ci-Cïj-alkoxy;Rs is hydrogen, or (Ci-C^)-alkyl or (C3-C6)-cycloaikyl, each substituted by m radicals from 20 the group consisting of fluorine, chlorine and (Ci-Cî)-alkoxy;R11 is hydrogen or (Ci-C3)-alkyl;R12 is OR7, S(O)nR5, SO2NR6R7, or (Ci-Ccj-alkyl substituted in each case by m radicals 25 from the group consisting of fluorine, chlorine, cyano, OR7 and S(O)nR5;orR11 and R12 together with the nitrogen atom to which they are bonded form a saturated or 30 partly or fully unsaturated five- or sîx-membered ring which is optionally mono- to trisubstituted by radicals from the group consisting of halogen, (CiCû)-alkyl, halo-(Ci-Cû)-alkyl and oxo and which, in addition to that nitrogen atom, contains r carbon atoms, o oxygen atoms, p sulfur atoms and q éléments from the group consisting of N R7 and NCOR7 as ring atoms;152the index m is 0, 1, 2 or 3;the index n is 0, 1 or 2;the index o is 0, 1 or 2;the index p is 0 or 1;10 the index q is 0 or 1; and the index r is 3, 4 or 5.
- 4. Composition according to any of Claîms 1 to 3, where component (B) is one or more active15 ingrédients selected from (B1.7) mesotrione, (B1.8) pinoxaden, (B1.14) tembotrione, (B2.3) amidosulfuron, (B2.18) diflufenican, (B2.24) flazasulfuron, (B2.25) florasulam, (B2.26) flucarbazone, (B2.28) flufenacet, (B2.31) foramsulfuron, (B2.34) îodosulfuron, (B2.37) mesosulfuron, (B2.58) propyzamide.(B2.68) thiencarbazone, (B2.69) tbifensulfuron, (B2.72) tribenuron, (B3.1) bromoxynil, (B4.18) isoxaflutole.(B4.22) pyrasulfotole, (B4.25) pyroxasulfone,153 (B5.23) (B5.31) (B5.38) florpyrauxifen, halauxifen, pelargonic acid.(B6.2) (B6.3) (B6.4) clopyralid, dicamba, fluroxypyr, (B7.4) (B7.5) glufosinate, giyphosate, (B8.1) (B8.5) 2,4-D, aclonifen, (B9.10) saflufenacil.(B11.5) (B11.6) (B 11.8) hexazinone, indazîflam, metribuzin.
- 5. Composition according to Claim 1, comprising a component (A) selected from:5 Al, A2, A3, A4, A5, A6, A7 and A8, or an agrochemically acceptable sait of these compounds, where compounds A1-A8 are defined as follows:Al154155and one or more components (B) selected from (B 1.7) (B1.8) (B 1.14) mesotrione, pinoxaden, tembotrione, (B2.3) (B2.18) (B2.24) (B2.25) (B2.26) (B2.28) (B2.31) (B2.34) (B2.37) (B2.58) (B2.68) (B2.69) (B2.72) (B3.1) amidosulfuron, diflufenican, flazasulfuron, florasulam, flucarbazone, flufenacet, foramsulfuron, iodosulfuron, mesosulfuron, propyzamide, thiencarbazone, thifensulfuron, tribenuron, bromoxynil.(B4.18) (B4.22) (B4.25) isoxaflutole, pyrasulfotole, pyrox a sulfone.(B5.23) (B5.31) (B5.38) florpyrauxifen, halauxifen, pelargonic acid, (B6.2) (B6.3) clopyralid, dicamba,156 (B6.4) fluroxypyr.(B7.4) (B7.5) glufosinate, glyphosate, (B8.1) (B8.5) 2,4-D, aclonifen, (B9.10) saflufenacil, (B11.5) (B11.6) (BU .8) hexazinone, indaziflam, metribuzin.
- 6. Composition according to Claim 1, comprising a component (A) selected from:Al and A8, or an agrochemically acceptable sait of these compounds, where compounds Al and A8 are defined as follows:one or more components (B) selected from (B1.7) mesotrione,157 (B1.8) (B1.14) pinoxaden, tembotrione, (B2.3) (B2.18) (B2.24) (B2.25) (B2.26) (B2.28) (B2.31) (B2.34) (B2.37) (B2.58) (B2.68) (B2.69) (B2.72) (B3.1) amidosulfuron, dîflufenican, flazasulfuron, florasulam, flucarbazone, flufenacet, foramsulfuron, iodosulfuron, niesosulfuron, propyzamide, thiencarbazone, thifensulfuron, tribenuron, bromoxynil, (B4.18) (B4.22) (B4.25) isoxaflutole, pyrasulfotole, pyroxasulfone.(B5.23) (B5.31) (B5.38) florpyrauxifen, halauxifen, pelargonic acid, (B6.2) (B6.3) (B6.4) clopyralid, dicamba, fluroxypyr, (B7.4) (B7.5) glufosinate, glyphosate.(B8.1) (B8.5) 2,4-D, aclonifen, (B9.10) saflufenacil.158(BU.5) (BU.6) (B11.8) hexazinone, indaziflam, metribuzin.
- 7. Composition according to Claim 1, comprising a component (A):Al, or an agrochemically acceptable sait of these compounds, where compounds Al are defined as follows:Alone or more components (B) selected from (B1.7) mesotrione.(B1.8) pinoxaden.(B1.14) tembotrione, (B2.3) amidosulfuron, (B2.18) diflufenican, (B2.24) flazasulfuron, (B2.25) florasulam, (B2.26) flucarbazone, (B2.28) flufenacet, (B231) foramsulfuron, (B2.34) iodosulfuron, (B2.37) mesosulfuron.(B2.58) propyzamide, (B2.68) thiencarbazone, (B2.69) thifensulfuron, (B2.72) tribenuron, (B3.1) bromoxynil,159 (B4.18) (B4.22) isoxaflutole, pyrasulfotole, (B4.25) pyroxasulfone.(B5.23) (B5.31) (B5.38) llorpyrauxifen, halauxifen, peïargonic acid, (B6.2) (B6.3) (B6.4) clopyralid, dicamba, fluroxypyr.(B7.4) (B7.5) glufosinate, glyphosate, (B8.1) (B8.5) 2,4-D, aclonifen, (B9.10) saflufenacil, (B11.5) (B11.6) (B 11,8) hexazinone, indaziflam, metribuzin.
- 8. Composition according to Claim 1, comprising a component (A):Al, or an agrociremicaily acceptable sait of these compounds, where compounds Al are defined as follows:Alone or more components (B) selected from (B2.18) diflufenican, (B2.28) flufenacet.160 (B2.31) (B2.37) (B2.58) (B2.68) (B3.1) foramsulfuron, mesosulfuron, propyzamide, thiencarbazone, bromoxynil.(B4.22) (B5.31) (B7.4) (B7.5) pyrasulfotole, halauxifen, glufosinate, glyphosate, (B11.6) indaziflam.
- 9. Herbicidal composition according to any of Claims 1 to 8, comprising the active ingrédient components (A) and (B) in a weight ratio of from 1:100 000 to 2000:1.5
- 10. Herbicidal composition according to any of Claims 1 to 8, comprising the active ingrédient components (A) and (B) in a weight ratio of from 1:15 000 to 500:1.
- 11. Herbicidal composition according to any of Claims 1 to 10, comprising one or more further components from the group comprising other kînds of active crop protection ingrédients.
- 12. Herbicidal product comprising a herbicidal composition according to any of Claims 1 to 11 and one 10 or more additives customary in crop protection.
- 13. Method of controlling harmful plants or of regulating the growth of plants, wherein the active ingrédient components of the herbicidal composition or herbicidal product according to any of Claims 1 to 12 are applied to the plants, plant parts, plant seeds or the area under cultivation.
- 14. Method according to Claim 13, wherein the active ingrédient components of the herbicidal 15 composition or herbicidal product according to any of Claims 1 to 12 are applied to the plants, plant parts, plant seeds or the area under cultivation jointly or separately by the pre-emergence method, the post-emergence method or by the pre- and post-emergence method.
- 15. Method according to Claim 13 or 14, wherein the herbicide component (A) is applied at an application rate of 0.01 to 1000 g a.i./ha.161A
- 16. Method accordîng to Claim 13 or 14, wherein the herbicide component (B) is applied at an application rate of 0.01 to 4000 g a.i./ha, except for pelargonic acid, which is applied at an application rate of 1 to 100 000 g a.i./ha.
- 17. Method accordîng to any of Claims 13 to 16 for controlling harmful plants by treatment before5 sowing of the crop plants and in plantation crops, and on uncultivated land.
- 18. Method accordîng to any of Claims 13 to 17, wherein the active ingrédients of the herbicidal composition are applied in the form of a herbicidal product accordîng to Claim 12 comprising one or more additives customary in crop protection, optionally after dilution with water.
- 19. Use of the herbicidal composition or herbicidal product accordîng to any of Claims 1 to 12 for 10 controlling harmful plants or for regulating the growth of plants.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP19184436.4 | 2019-07-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| OA20567A true OA20567A (en) | 2022-10-27 |
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