BR112020008601B1 - COMPOUNDS, AGROCHEMICAL COMPOSITION, USE OF COMPOUNDS, METHOD TO COMBAT HARMFUL PHYTOPATHOGENIC FUNGI AND COATED SEED - Google Patents

Abstract

The present invention relates to trifluoromethyl oxadiazoles of formula I, or the N-oxides, or the agriculturally useful salts thereof; to a process for preparing compounds of formula I; to intermediates which are useful in preparing compounds of formula I; the use of compounds of formula I to control harmful phytopathogenic fungi; to a method for combating harmful phytopathogenic fungi, which process comprises treating the fungi, plants, soil or seeds to be protected against fungal attack, with an effective amount of at least one compound of formula I, or an N- oxide, or an agriculturally acceptable salt thereof; and to agrochemical compositions comprising at least one compound of formula I, or an N-oxide, or an agriculturally acceptable salt thereof; and agrochemical compositions that still comprise seeds.

Description

[001] The present invention relates to trifluoromethyl oxadiazoles of formula I, or the N-oxides, or the agriculturally useful salts thereof; to a process for preparing compounds of formula I; to intermediates which are useful in preparing compounds of formula I; the use of compounds of formula I to control harmful phytopathogenic fungi; to a method for combating harmful phytopathogenic fungi, which process comprises treating the fungi, plants, soil or seeds to be protected against fungal attack, with an effective amount of at least one compound of formula I, or an N- oxide, or an agriculturally acceptable salt thereof; and to agrochemical compositions comprising at least one compound of formula I, or an N-oxide, or an agriculturally acceptable salt thereof; and agrochemical compositions that still comprise seeds.

[002] 5-Trifluoromethyl-1,2,4-oxadiazoles are known as fungicides from documents WO 2017/162868 A1 and WO 2017/118689 A1.

[003] In many cases, in particular, at low application rates, the fungicidal activity of known fungicidal compounds is unsatisfactory. Based on this, it was an object of the present invention to provide compounds that have improved activity and/or a broader spectrum of activity against phytopathogenic fungi. Another object of the present invention is to provide fungicides with improved toxicological properties. This objective is achieved by the oxadiazole compounds of formula I, or the N-oxides, or their salts that are agriculturally useful for controlling phytopathogenic fungi.

[004] The compounds according to the invention differ from those described in the prior art closer to the nature of the W group.

[005] Consequently, the present invention relates to compounds of formula I, or the N-oxides, or the agriculturally acceptable salts thereof,

[006] where: A is phenyl or a 5- or 6-membered aromatic heterocycle; wherein the ring member atoms of the aromatic heterocycle include in addition to carbon atoms, 1, 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms with the proviso that the heterocycle cannot contain 2 contiguous atoms selected from O and S; and wherein the phenyl ring or aromatic heterocycle is unsubstituted or substituted by 1, 2, 3 or 4 identical or different RA groups; where RA is halogen, cyano, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy or C1-C6 haloalkoxy; W is a 3- or 4-membered non-aromatic heterocycle that contains as ring member atoms, in addition to carbon atoms, 1 nitrogen atom; wherein the heterocycle is attached to the L group through said ring member nitrogen atom; and wherein the heterocycle is linked to group A through one of the ring member carbon atoms; and wherein the heterocycle is further unsubstituted or substituted by 1, 2, 3 or 4 identical or different RW radicals; wherein RW is halogen, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy or C1-C3 haloalkoxy; L is -C(=O)-, -C(=S)-, -S(=O)p-, -C(=O)-O-#, -C(=O)NR2-# or - C (=S)NR2-#; where # denotes the position, in which it is linked to the radical R1; and where p is 0, 1 or 2; R2 is hydrogen, formyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C5 cycloalkyl, C1-C6 alkoxy or C1-C6 haloalkyl; R1 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C3-C6 alkynyl, C1-C6-alkoxyimino-C1-C4-alkyl, C2-C6-alkenyloxyimino-C1-C4-alkyl, C2-C6-alkynyloxyimino-C1 -C4-alkyl, C3-C11 cycloalkyl, C3-C11 cycloalkenyl, C3-C11-cycloalkyl-C1-C4-alkyl, phenyl-C1-C4-alkyl, heterocyclyl-C1-C4-alkyl, heteroaryl-C1-C4-alkyl , phenyl, naphthyl or mono- or bicyclic, saturated, partially unsaturated or aromatic heterocycle of 3 to 10 members, wherein the member atoms of the ring of said mono- or bicyclic heterocycle include in addition to carbon atoms, plus 1, 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms with the proviso that the heterocycle cannot contain 2 contiguous atoms selected from O and S; and wherein 1 or 2 member atoms of the carbon ring of the heterocycle may be replaced by 1 or 2 groups, independently selected from C(=O) and C(=S); and wherein the heterocyclyl group in heterocyclyl-C1-C4-alkyl is a saturated, partially unsaturated, 3- to 10-membered mono- or bicyclic heterocycle, wherein the ring member atoms of said mono- or bicyclic heterocycle include in addition of carbon atoms, plus 1, 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms, with the proviso that the heterocycle cannot contain 2 contiguous atoms selected from O and S; and wherein 1 or 2 member atoms of the carbon ring of the heterocycle may be replaced by 1 or 2 groups, independently selected from C(=O) and C(=S); and wherein the heteroaryl group in heteroaryl-C1-C4-alkyl is a 5- or 6-membered aromatic heterocycle, wherein the ring member atoms of the aromatic heterocycle include, in addition to carbon atoms, 1, 2, 3 or 4 selected heteroatoms from N, O and S as ring member atoms with the proviso that the heterocycle cannot contain 2 contiguous atoms selected from O and S; and wherein any of the aliphatic or cyclic R1 groups are unsubstituted or substituted by 1, 2, 3 or up to the maximum possible number of identical or different R1a groups; where R1a is halogen, cyano, C1-C6 alkyl, C1-C6 alkoxy or C1-C6 haloalkoxy.

[007] Agriculturally acceptable salts of the compounds of formula I especially include the salts of these cations or the acid addition salts of these acids whose cations and anions, respectively, have no adverse effect on the fungicidal action of the compounds I. Suitable cations are thus in particular, the ions of the alkali metals, preferably sodium and potassium, the alkaline earth metals, preferably calcium, magnesium and barium, the transition metals, preferably manganese, copper, zinc and iron, and also the ammonium ion which, if desired, may be substituted by one to four C1-C4 alkyl substituents and/or a phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, in addition, phosphonium ions, sulfonium ions, preferably tri(C1-C4 -alkyl)sulfonium and sulfoxonium ions, preferably tri(C1-C4-alkyl)sulfoxonium.

[008] Acceptable acid addition salt anions are mainly chloride, bromide, fluoride, hydrogensulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and the anions of C1-C4 alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting a compound I with an acid of the corresponding anion, preferably hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.

[009] Compounds of formula I can exist as one or more stereoisomers. The various stereoisomers include enantiomers, diastereomers, atropisomers arising from restricted rotation about a single bond of asymmetric groups, and geometric isomers. They also form part of the subject matter of the present invention. One skilled in the art will consider that a stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to other stereoisomers or when separated from other stereoisomers. Furthermore, those skilled in the art know how to selectively separate, enrich and/or prepare said stereoisomer. The compounds of the invention may be present as a mixture of stereoisomers, for example, a racemate, individual stereoisomers or as an optically active form.

[0010] Compounds of formula I may be present in different crystal modifications whose biological activity may differ. They also form part of the subject matter of the present invention.

[0011] Regarding variables, the realizations of the intermediates obtained during the preparation of compounds I correspond to the realizations of compounds of formula I. The term “compounds I” refers to compounds of formula I.

[0012] In the definitions of the variables given above, collective terms are used that are generally representative for the substituents in question. The term “Cn-Cm” indicates the number of carbon atoms possible in each case in the substituent or substituent component in question.

[0013] The term “halogen” refers to fluorine, chlorine, bromine and iodine.

[0014] The term “oxo” refers to an oxygen atom =O, which is bonded to a carbon atom or sulfur atom, thus forming, for example, a ketonyl group -C(=O)- or sulfinyl -S(=O)-.

[0015] The term “C1-C6 alkyl” refers to a straight or branched chain saturated hydrocarbon group that has 1 to 6 carbon atoms, for example, methyl, ethyl, propyl, 1-methylethyl, butyl, 1- methylpropyl, 2-methylpropyl and 1,1-dimethylethyl.

[0016] The term “C2-C6 alkenyl” refers to a straight or branched chain unsaturated hydrocarbon radical that has 2 to 6 carbon atoms and a double bond in any position, such as ethenyl, 1-propenyl, 2-propenyl (allyl), 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1- propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2- propenyl.

[0017] The term “C2-C6 alkynyl” refers to a straight or branched chain unsaturated hydrocarbon radical that has 2 to 6 carbon atoms and that contains at least one triple bond, such as ethynyl, 1-propynyl, 2- propynyl (propargyl), 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl.

[0018] The term “C1-C6 haloalkyl” refers to a straight or branched chain alkyl group having 1 to 6 carbon atoms (as defined above), wherein some or all of the hydrogen atoms in these groups may be substituted by halogen atoms as mentioned above, for example, chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2, 2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, CH2-C2F5, CF2-C2F5, CF(CF3)2, 1-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl, 1-(bromomethyl)-2- bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl or nonafluorobutyl.

[0019] The term “C1-C6 alkoxy” refers to a straight or branched chain alkyl group having 1 to 6 carbon atoms (as defined above) that is bonded through an oxygen, in any position in the alkyl group , for example, methoxy, ethoxy, n-propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or 1,1-dimethylethoxy.

[0020] The term “C1-C6 haloalkoxy” refers to a C1-C6 alkoxy group as defined above, in which some or all of the hydrogen atoms may be replaced by halogen atoms as mentioned above, e.g. , OCH2F, OCHF2, OCF3, OCH2Cl, OCHCl2, OCCl3, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2 -chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, OC2F5, 2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy , 2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, OCH2-C2F5, OCF2 -C2F5, 1-(CH2F)-2-fluoroethoxy, 1-(CH2Cl)-2-chloroethoxy, 1-(CH2Br)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy.

[0021] The terms “C3-C11-cycloalkyl-C1-C4-alkyl, heterocyclyl-C1-C4-alkyl, phenyl-C1-C4-alkyl or heteroaryl-C1-C4-alkyl” refer to alkyl that has 1 to 4 carbon atoms (as defined above), wherein a hydrogen atom of the alkyl radical is replaced by a cycloalkyl, heterocyclyl, phenyl or heteroaryl radical, respectively.

[0022] The term “C1-C4-alkoxy-C1-C4-alkyl” refers to an alkyl that has 1 to 4 carbon atoms (as defined above), in which one hydrogen atom of the alkyl radical is replaced by a C1-C4 alkoxy group (as defined above).

[0023] The term “C2-C6 alkenyl” refers to a straight or branched chain unsaturated hydrocarbon radical that has 2 to 6 carbon atoms and a double bond in any position, such as ethenyl, 1-propenyl, 2-propenyl (allyl), 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1- propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2- propenyl.

[0024] The term “C2-C6 alkynyl” refers to an unsaturated straight or branched chain hydrocarbon radical that has 2 to 6 carbon atoms and that contains at least one triple bond, such as ethynyl, 1-propynyl, 2- propynyl (propargyl), 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl.

[0025] The term “C3-C8 cycloalkyl” refers to monocyclic saturated hydrocarbon radicals that have 3 to 8 carbon ring members such as cyclopropyl (C3H5), cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl.

[0026] The term “C3-C11 cycloalkyl” refers to a univalent monocyclic, bicyclic or tricyclic hydrocarbon radical that has 3 to 11 carbon ring members that are connected through one of the ring carbon atoms by substitution of a hydrogen atom, such as cyclopropyl (C3H5), cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, bicyclo[1.1.0]butyl, bicyclo[2.1.0]pentyl, bicyclo[1.1.1]pentyl, bicyclo[3.1.0] hexyl, bicyclo[2.1.1]hexyl, norcaranyl (bicyclo[4.1.0]heptyl) and norbornyl (bicyclo[2.2.1]heptyl). Additional examples of bicyclic or tricyclic cycloalkyl radicals are found in the present application as embodiments R1.1 to R1.26.

[0027] The term “C1-C6-alkoxyimino-C1-C4-alkyl” refers to an alkyl that has 1 to 4 carbon atoms, in which two hydrogen atoms of one carbon atom of the alkyl radical are replaced by one bivalent C1-C6 alkoxyimino radical (C1-C6-alkyl-O-N=), as defined above.

[0028] The term “C2-C6-alkenyloxyimino-C1-C4-alkyl” refers to an alkyl that has 1 to 4 carbon atoms, in which two hydrogen atoms of one carbon atom of the alkyl radical are replaced by one bivalent C2-C6 alkenyloxyimino radical (C2-C6-alkenyl-O-N=).

[0029] The term “C2-C6-alkynyloxyimino-C1-C4-alkyl” refers to an alkyl that has 1 to 4 carbon atoms, in which two hydrogen atoms of one carbon atom of the alkyl radical are replaced by one bivalent C2-C6 alkynyloxyimino radical (C2-C6-alkynyl-O-N=).

[0030] The term “formyl” refers to a -C(=O)H group.

[0031] The term “aliphatic” refers to compounds or radicals composed of carbon and hydrogen and which are non-aromatic compounds. An “alicyclic” compound or radical is an organic compound that is both aliphatic and cyclic. They contain one or more carbon rings that can be either saturated or unsaturated, but do not have an aromatic character.

[0032] The terms “cyclic component” or “cyclic group” refer to a radical, which is an alicyclic ring or an aromatic ring such as, for example, phenyl or heteroaryl.

[0033] The term "and wherein any of the aliphatic or cyclic groups R1 are unsubstituted or substituted by..." refers to aliphatic groups, cyclic groups and groups that contain an aliphatic and a cyclic component in a group such as , for example, C3-C11-cycloalkyl-C1-C4-alkyl or phenyl-C1-C4-alkyl; therefore, a group that contains an aliphatic and a cyclic component, both of these components can be substituted or unsubstituted independently of each other.

[0034] The term “phenyl” refers to an aromatic ring system that includes six carbon atoms (commonly referred to as a benzene ring. In association with group A, the term “phenyl” should be interpreted as a benzene ring or phenylene ring, which is linked to both the oxadiazole component and the L group.

[0035] The term "heteroaryl", unless otherwise defined, refers to monocyclic or polycyclic aromatic ring systems that include, in addition to carbon atoms, 1, 2, 3 or 4 heteroatoms independently selected from the group consisting of N, O and S as ring member atoms, with the proviso that the heterocycle cannot contain 2 contiguous atoms selected from O and S.

[0036] The term “3- to 7-membered saturated carbocycle” should be understood to mean monocyclic saturated carbocycles that have 3, 4 or 5 carbon ring members. Examples include cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, and the like.

[0037] The term “mono- or bicyclic, saturated, partially unsaturated or aromatic heterocycle of 3 to 10 members, wherein the member atoms of the ring of said mono- or bicyclic heterocycle include in addition to carbon atoms, plus 1, 2, 3 or 4 heteroatoms selected from N, O and S as member atoms of the ring with the proviso that the heterocycle cannot contain 2 contiguous atoms selected from O and S”, is to be understood as meaning both, systems of mono- and bicyclic aromatic heteroaromatic rings as well as saturated and partially unsaturated heterocycles, for example:

[0038] a 3- or 4-membered saturated heterocycle that contains 1 or 2 heteroatoms from the group consisting of N, O and S as ring members such as oxirane, aziridine, thiirane, oxetane, azetidine, thiethane, [1,2]dioxetane , [1,2]dithiethane, [1,2]diazetidine;

[0039] and a saturated or partially unsaturated 5- or 6-membered heterocycle that contains 1, 2 or 3 heteroatoms from the group consisting of N, O and S as ring members such as 2-tetrahydrofuranyl, 3-tetra- hydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 1,2,4-oxadiazolidin-3- yl, 1,2,4- oxadiazolidin-5-yl, 1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl, 1,2,4- triazolidin-3-yl, 1,3,4-oxadiazolidin-2-yl, 1,3,4-thiadiazolidin-2-yl, 1,3,4-triazolidin-2-yl, 2,3-dihydrofur-2-yl, 2, 3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3-dihydrothien-2-yl, 2,3- dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl, 2-pyrrolin-2-yl, 2-pyrrolin-3-yl, 3- pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin-3-yl, 2-isoxazolin- 4-yl, 3-isoxazolin- 4-yl, 4-isoxazolin-4-yl, 2-isoxazolin-5-yl, 3-isoxazolin-5-yl, 4-isoxazolin-5-yl, 2-isothiazolin-3-yl, 3-isothiazolin-3- yl, 4-isothiazolin-3-yl, 2-isothiazolin-4-yl, 3-isothiazolin-4-yl, 4-isothiazolin-4-yl, 2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl, 2,3-dihydropyrazol-1-yl, 2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3-di- hydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1-yl, 3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol- 4-yl, 3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-1-yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl, 4, 5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl, 2,3-di- hydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 1,3- dioxan-5-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothienyl, 3-hexahydropyridazinyl, 4-hexahydropyridazinyl, 2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl, 5-hexahydropyrimidinyl, 2-piperazinyl, 1,3,5-hexahydrotriazin-2-yl and 1,2,4-hexahydrotriazin-3-yl and also the corresponding -ylidene radicals; It is

[0040] a saturated or partially unsaturated 7-membered heterocycle such as tetra- and hexahydroazepinyl, such as 2,3,4,5-tetrahydro[1H]azepin- 1-,-2-,-3-,-4 -,-5-,-6- or-7-yl, 3,4,5,6-tetrahydro[2H]azepin-2-,-3-,-4-,-5-,-6- or -7- yl, 2,3,4,7-tetrahydro[1H]azepin-1-,-2-,-3-,-4-,-5-,-6- or-7-yl, 2 ,3,6,7-tetrahydro[1H]azepin-1-,-2-,-3-,-4-,-5-,-6-or-7-yl, hexahydroazepin-1-, -2-,-3- or-4-yl, tetra- and hexahydrooxepinyl as 2,3,4,5-tetrahydro[1H]oxepin-2-,-3-,-4-,-5- ,-6- or-7-yl, 2,3,4,7-tetrahydro[1H]oxepin-2-,-3-,-4-,-5-,-6- or-7-yl, 2,3,6,7-tetrahydro[1H]oxepin-2-, -3-,-4-,-5-,-6- or-7-yl, hexahydroazepin-1-,-2- ,-3-or-4-yl, tetra- and hexahydro-1,3-diazepinyl, tetra- and hexahydro-1,4-diazepinyl, tetra- and hexahydro-1,3-oxazepinyl, tetra - and hexahydro-1,4-oxazepinyl, tetra- and hexahydro-1,3-dioxepinyl, tetra- and hexahydro-1,4-dioxepinyl and the corresponding -ylidene radicals.

[0041] The term “5- or 6-membered heteroaryl” or the term “5- or 6-membered aromatic heterocycle” refers to aromatic ring systems that include, in addition to carbon atoms, 1, 2, 3 or 4 heteroatoms independently selected from the group consisting of N, O and S, for example, a 5-membered heteroaryl such as pyrrole-1-yl, pyrrole-2-yl, pyrrole-3-yl, thien-2-yl, thien-3 -yl, furan-2-yl, furan-3-yl, pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1-yl, imidazol-2-yl , imidazol-4-yl, imidazol-5-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, thiazole -2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1,2,4-triazolyl-1-yl, 1,2 ,4-triazol-3-yl, 1,2,4-triazol-5-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl and 1,2,4- thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl; or

[0042] a 6-membered heteroaryl, such as pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4- yl, pyrimidin-5-yl, pyrazin-2-yl and 1,3,5-triazin-2-yl and 1,2,4-triazin-3-yl.

[0043] Regarding variables, the realizations of the intermediates correspond to the realizations of compounds I. Preference is given to compounds I and, when applicable, also to compounds of all subformulas provided in the present application, for example, formulas I.1, I.2, I.A, I.B, I.C, I.D, I.E, I.F, I.G, I.H and I.J, in which the variables A, RA, W, RW, L, p, R1, R1a, R2, have independently of each other or more preferably in combination (any possible combination of 2 or more substituents, as defined in the present application) the following meanings:

[0044] In one aspect of the invention, group A is phenyl, which is unsubstituted or substituted by 1, 2, 3 or 4 identical or different RA groups, as defined or preferably defined in the present application and in which group W is attached to the phenyl ring in the para position relative to the oxadiazole group.

[0045] In one aspect of the invention, A is phenyl, which is unsubstituted or substituted by 1, 2, 3 or 4 identical or different RA groups, as defined or preferably defined in the present application and in which the W group is attached to the phenyl ring in the meta position in relation to the oxadiazole group.

[0046] In one aspect of the invention, A is phenyl, which is substituted by 1 or 2 identical or different RA groups, as defined or preferably defined in the present application and in which the W group is attached to the phenyl ring in the para position relative to to the oxadiazole group.

[0047] In one embodiment, A is a 6-membered aromatic heterocycle, wherein the aromatic heterocycle ring member atoms include in addition to 1 carbon atom or 2 nitrogen atoms as ring member atoms; and wherein the aromatic heterocycle is unsubstituted or substituted by 1 or 2 identical or different RA groups, as defined or preferably defined in the present application; particularly RA is chlorine, fluorine or methyl.

[0048] In a further embodiment, A is a 6-membered aromatic heterocycle, wherein the aromatic heterocycle ring member atoms include in addition to 1 carbon atom or 2 nitrogen atoms as ring member atoms; and wherein the aromatic heterocycle is unsubstituted or substituted by 1 or 2 identical or different RA groups, as defined or preferably defined in the present application; particularly RA is chlorine, fluorine or methyl; and wherein the W group is attached to the 6-membered aromatic heterocycle in the para position relative to the oxadiazole group.

[0049] In a more preferred embodiment, A is a 5-membered aromatic heterocycle, in particular, a thiophene ring, more particularly a 2,5-thiophenyl ring, in which the member atoms of the heterocycle ring include in addition to carbon atoms , 1, 2, 3 or 4 heteroatoms selected from N, O and S as the member atoms of the ring with the proviso that the heterocycle cannot contain 2 contiguous atoms selected from O and S; and wherein the cyclic groups A are unsubstituted or substituted by 1 or 2 identical or different RA groups, as defined or preferably defined in the present application; particularly RA is chlorine, fluorine or methyl.

[0050] In one embodiment, the invention relates to compounds of formula I, in which component A is defined as in subformulas (A.1) to (A.30),

[0051] where #1 denotes the position, which is connected to the oxadiazole component and #2 denotes the position, which is connected to the W of compounds of formula I; and wherein A is unsubstituted or substituted by 1 or 2 identical or different RA groups and wherein RA is as defined or preferably defined in the present application. In another embodiment, A as defined in any of subformulas (A.1) to (A.30) is unsubstituted or substituted by 1 or 2 identical or different RA groups; and where RA is chlorine, fluorine or methyl. In a preferred embodiment, A as defined in any of subformulas (A.1) to (A.30) is unsubstituted.

[0052] In a preferred embodiment, RA is independently selected from the group consisting of halogen, C1-C6 alkyl or C3-C8 cycloalkyl. In another preferred embodiment, RA is independently selected from the group consisting of halogen, methyl or ethyl. More preferably RA is independently selected from the group consisting of halogen, in particular, RA is fluorine.

[0053] Additional realizations regarding the meaning of the W group are as follows:

ACHIEVEMENT W.1

[0054] W is selected from the groups Wa, Wb and Wc,

[0055] where # denotes the position in which it is fixed to group A and the dashed line denotes the position in which it is fixed to R1; and wherein W is further unsubstituted or substituted by 1, 2, 3 or 4 identical or different RW radicals; wherein RW is halogen, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy or C1-C3 haloalkoxy; preferably RW is halogen or C1-C3 alkyl.

ACHIEVEMENT W.2

[0056] W is group W.b as defined in Embodiment W.1, wherein W is not yet substituted or substituted by 1 or 2 identical or different RW radicals; wherein RW is halogen, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy or C1-C3 haloalkoxy; preferably RW is halogen or C1-C3 alkyl.

ACHIEVEMENT W.3

[0057] W is group W.a as defined in Embodiment W.1, wherein W is not yet substituted or substituted by 1 or 2 identical or different radicals RW; wherein RW is halogen, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy or C1-C3 haloalkoxy; preferably RW is halogen or C1-C3 alkyl.

[0058] Additional realizations regarding the meaning of the L group are as follows:

ACHIEVEMENT L.1

[0059] L is -C(=O)-, -C(=S)- or -S(=O)p-; and where p is 0, 1 or 2.

ACHIEVEMENT L.2

[0060] L is -S(=O)2-.

ACHIEVEMENT L.3

[0061] L is -C(=O)- or -C(=S)-.

ACHIEVEMENT L.4

[0062] L is -C(=O)-O-#, -C(=O)NR2-# or -C(=S)NR2-#; where # denotes the position, in which it is linked to the radical R1; and wherein R2 is hydrogen, formyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C5 cycloalkyl, C1-C6 alkoxy or C1-C6 haloalkyl.

ACHIEVEMENT L.5

[0063] L is -C(=O)NR2-#; where # denotes the position, in which it is linked to the radical R1; and where R2 is hydrogen, formyl, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, methoxy, ethioxy, n-propyloxy, iso-propyloxy, cyclopropyl , cyclopropyl-CH2-, allyl or propargyl.

[0064] Additional realizations regarding the meaning of the radical R1 are as follows:

ACHIEVEMENT 1.1

[0065] R1 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6-alkoxyimino-C1-C4-alkyl, C2-C6-alkenyloxyimino-C1-C4-alkyl, C2-C6- alkynyloxyimino-C1-C4-alkyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, C3-C8-cycloalkyl-C1-C4-alkyl, phenyl-C1-C4-alkyl, heteroaryl-C1-C4-alkyl, phenyl, or a 5- or 6-membered aromatic heterocycle, wherein the ring member atoms of the aromatic heterocycle include in addition to carbon atoms 1, 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms with the proviso that the heterocycle cannot contain 2 contiguous atoms selected from O and S; and wherein the heteroaryl group in heteroaryl-C1-C4-alkyl is a 5- or 6-membered aromatic heterocycle, wherein the ring member atoms of the aromatic heterocycle include, in addition to carbon atoms, 1, 2, 3 or 4 selected heteroatoms from N, O and S as ring member atoms with the proviso that the heterocycle cannot contain 2 contiguous atoms selected from O and S; and wherein any of the aliphatic or cyclic groups R1 are unsubstituted or substituted by 1, 2, 3 or up to the maximum possible number of identical or different radicals selected from the group consisting of halogen, cyano, C1C6 alkyl, C1 haloalkyl -C6, C1-C6 alkoxy, C1-C6 haloalkoxy and C3-C8 cycloalkyl.

ACHIEVEMENT 1.2

[0066] R1 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C3C6 alkynyl or C3-C11 cycloalkyl.

ACHIEVEMENT 1.3

[0067] R1 is hydrogen, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl or cyclopropyl.

ACHIEVEMENT 1.4

[0068] R1 is phenyl or heteroaryl; and wherein the heteroaryl group is a 5- or 6-membered aromatic heterocycle, wherein the ring includes in addition to carbon atoms, 1, 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms with the condition that the heterocycle cannot contain 2 contiguous atoms selected from O and S; and wherein any of the cyclic groups are unsubstituted or substituted by 1, 2, 3 or up to the maximum possible number of identical or different radicals selected from the group consisting of halogen, cyano, C1-C6 alkyl, C1-haloalkyl C6, C1-C6 alkoxy, C1-C6 haloalkoxy and C3-C8 cycloalkyl.

ACHIEVEMENT 1.5

[0069] R1 is C3-C11 cycloalkyl or C3-C11 cycloalkenyl; and wherein the cyclic group is unsubstituted or substituted by 1, 2, 3 or up to the maximum possible number of identical or different radicals selected from the group consisting of halogen, oxo, cyano, C1-C6 alkyl, C1-haloalkyl C6, C1-C6 alkoxy, C1-C6 haloalkoxy and C3-C8 cycloalkyl.

ACHIEVEMENT 1.6

[0070] R1 is C1-C6 alkyl; and wherein the alkyl group is unsubstituted or substituted by 1, 2, 3 or up to the maximum possible number of identical or different radicals selected from the group consisting of halogen, oxo, cyano, C1-C6 alkyl, C1-haloalkyl C6, C1-C6 alkoxy, C1-C6 haloalkoxy and C3-C8 cycloalkyl.

ACHIEVEMENT 1.7

[0071] R1 is difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl , 3,3,3-trifluoropropyl, CH2CF2CF3 or CF2CF2CF5, CH(CH3)CF3, CH2CF2CH3, CH2C(CH3)2F, CH2CH(CH3)CF3 or CH2C(CH3)2CF3.

ACHIEVEMENT 1.8

[0072] R1 is C1-C6-alkoxyimino-C1-C4-alkyl, C2-C6-alkenyloxyimino-C1-C4-alkyl or C2-C6-alkynyloxyimino-C1-C4-alkyl.

ACHIEVEMENT 1.9

[0073] R1 is selected from the group consisting of radicals R1.1 to R1.26 below, particularly from R1.1 to R1.18, which are further unsubstituted or substituted by 1 or 2 radicals selected from group consisting of methyl, ethyl, oxo hydroxyl and halogen; and where “#C” indicates the carbon atom, which is attached to the rest of the compounds of formula I.

[0074] In one embodiment, R1a is selected from the group consisting of halogen, oxo, cyano, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy and C3-C8 cycloalkyl.

[0075] In another aspect of the invention, R1a is selected from the group consisting of fluorine, chlorine, oxo, cyano, methyl, ethyl, methoxy, trifluoromethyl, trifluoromethoxy, difluoromethyl, difluoromethoxy and cyclopropyl.

[0076] In a preferred aspect of the invention, R1a is selected from the group consisting of halogen, oxo, C1-C6 alkyl and C3C8 cycloalkyl; particularly from oxo, methyl, ethyl, fluorine and chlorine; more particularly from fluorine and chlorine.

[0077] In additional aspects of the present invention, embodiments E.1 to E.84 listed in Table E represent preferred combinations of embodiments, which are defined in the present application above for each of the variables W, L and R1. TABLE E

[0078] In one embodiment, the invention relates to compounds of formula I, or the N-oxides, or the agriculturally acceptable salts thereof, wherein A is a group selected from subformulas (A.1) to ( A.30); and wherein the phenyl ring or aromatic heterocycle is unsubstituted or substituted by 1 or 2 identical or different RA groups; where RA is halogen, cyano, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy or C1-C6 haloalkoxy; W is selected from groups W.a, W.b and W.c, as defined in this application; and wherein W is further unsubstituted or substituted by 1, 2, 3 or 4 identical or different RW radicals; wherein RW is halogen, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy or C1-C3 haloalkoxy; L is -C(=O)-, -C(=S)-, -S(=O)p-, -C(=O)-O-#, -C(=O)NR2-# or - C (=S)NR2-#; where # denotes the position, in which it is linked to the radical R1; and where p is 0, 1 or 2; R2 is hydrogen, formyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C5 cycloalkyl, C1-C6 alkoxy or C1-C6 haloalkyl; R1 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6-alkoxyimino-C1-C4-alkyl, C2-C6-alkenyloxyimino-C1-C4-alkyl, C2-C6-alkynyloxyimino-C1 -C4-alkyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, C3-C8-cycloalkyl-C1-C4-alkyl, phenyl-C1-C4-alkyl, heteroaryl-C1-C4-alkyl, phenyl, or an aromatic heterocycle of 5 or 6 members, wherein the ring member atoms of the aromatic heterocycle include in addition to carbon atoms 1, 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms with the proviso that the heterocycle cannot contain 2 contiguous atoms selected from O and S; and wherein the heteroaryl group in heteroaryl-C1-C4-alkyl is a 5- or 6-membered aromatic heterocycle, wherein the ring member atoms of the aromatic heterocycle include, in addition to carbon atoms, 1, 2, 3 or 4 selected heteroatoms from N, O and S as ring member atoms with the proviso that the heterocycle cannot contain 2 contiguous atoms selected from O and S; and wherein any of the aliphatic or cyclic groups R1 are unsubstituted or substituted by 1, 2, 3 or up to the maximum possible number of identical or different radicals selected from the group consisting of halogen, cyano, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy and C3-C8 cycloalkyl.

[0079] In another embodiment, the invention relates to compounds of formula I, or the N-oxides, or the agriculturally acceptable salts thereof, wherein A is a phenyl ring; and wherein the phenyl ring is unsubstituted or substituted by 1 or 2 identical or different RA groups; where RA is halogen, cyano, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy or C1-C6 haloalkoxy; W is selected from groups W.a, W.b and W.c, as defined in this application; and wherein W is further unsubstituted or substituted by 1, 2, 3 or 4 identical or different RW radicals; wherein RW is halogen, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy or C1-C3 haloalkoxy; L is -C(=O)-, -C(=S)-, -S(=O)p-, -C(=O)-O-#, -C(=O)NR2-# or - C (=S)NR2-#; where # denotes the position, in which it is linked to the radical R1; and where p is 1 or 2; R2 is hydrogen, formyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C5 cycloalkyl, C1-C6 alkoxy or C1-C6 haloalkyl; R1 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C3-C6 alkynyl or C3-C8 cycloalkyl; preferably hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, sec-butyl, tert-butyl or cyclopropyl.

[0080] In one embodiment, the invention relates to compounds of formula I.1 or compounds of formula I.2, or N-oxides, or agriculturally acceptable salts thereof,

[0081]AemAqueAnAéA0,A1AorA2;AeAemAqueAoAqueAosAvariáveisAW,ARW,AL,AR1AeAR2AéAconformeAdefinidoYearPresentApparaCompoundsAof formulaAIAorAccordingAdefinedAnasAccomplishmentsAE.1AaAE.84AnaATableAE;AeAemAqueRAAqueAconformeAdefined AorApreferablyAdefinedYearPresentApplicationAparaA compoundsAdeAformulaAI.A

[0082] AThe preferred realizationA refers toAcompoundsAof formulaAI.1AorAaAcompoundsAdeAformulaAI.2AsdefinedAabove,AinAqueAoA meaningAofAvariablesAW,ARW,AL,AR1AandAR2AisAsdefinedAinthepresentapplicationAforAcompoundsAdeAformulaAIAorAsdefinedAnasArealizationsAE .1Aa E.84AnaATableAE;AeAemAqueAnAéA0AorA1AeARAAéAfluor.A

[0083]AInA further embodiment,The inventionArefersAtocompoundsAofFormulaAI.1,AorAAN-oxides,AorAgriculturallyacceptable saltsofthesame,AinAwhich:RAAisAfluorine; formdefinedYearPresentApplication;AinAWhichAWAisAyetDwarfAreplacedAorAreplacedA byA1AorA2AradicalsARWAidenticalAorAdifferent;AinAwhichAA RWA isA halogen,A cyano,AalkylAC1-C3,AhaloalkylAC1-C3,AalkoxyC1-C3AorAhaloalkoxyAC1-C3;ALA isA -C(=O)-,A -C(=S)-, A -S(=O)-,A -S(=O)2-,A -C(=O)-O-#,A - C(=O)NR2-#AorA-C(=S)NR2- # ; R1 is as defined in the present application for compounds of formula I, or as preferably defined in any of Embodiments 1.1 to 1.14.

[0084] In a further embodiment, the invention relates to compounds of formula I.1, or the N-oxides, or the agriculturally acceptable salts thereof, wherein: n is 0; W is selected from the groups W.a, W.b and W.c as defined in this application; wherein W is still unsubstituted or substituted by 1 or 2 identical or different RW radicals; wherein RW is halogen or C1-C3 alkyl; L is -C(=O)- or -S(=O)2-; R1 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C3-C6 alkynyl or C3-C11 cycloalkyl.

[0085] In a further embodiment, the invention relates to compounds of formula I.1, or the N-oxides, or the agriculturally acceptable salts thereof, wherein: n is 0; W is a group Wb as defined in the present application; wherein W is still unsubstituted or substituted by 1 or 2 identical or different RW radicals; wherein RW is halogen or C1-C3 alkyl; L is -C(=O)- or -S(=O)2-; R1 is as defined in the present application for compounds of formula I, or as preferably defined in any of Embodiments 1.1 to 1.14.

[0086] In a further embodiment, the invention relates to compounds of formula I.1, or the N-oxides, or the agriculturally acceptable salts thereof, wherein: n is 0; W is a group Wb as defined in the present application; wherein W is still unsubstituted or substituted by 1 or 2 identical or different RW radicals; wherein RW is halogen or C1-C3 alkyl; L is -C(=O)-, -C(=S)-, -S(=O)-, -S(=O)2-, -C(=O)-O-#, - C(= O)NR2-# or -C(=S)NR2-#; where # denotes the position, in which it is linked to the radical R1; and wherein R2 is hydrogen, formyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C5 cycloalkyl, C1-C6 alkoxy or C2-C6 haloalkyl; R1 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C3-C6 alkynyl or C3-C11 cycloalkyl; preferably hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, sec-butyl, tert-butyl or cyclopropyl.

[0087] In a further embodiment, the invention relates to compounds of formula I.1, or the N-oxides, or the agriculturally acceptable salts thereof, wherein: n is 0; W is a group Wb as defined in the present application; where W is not yet replaced; L is -C(=O)- or -S(=O)2-; R1 is hydrogen, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl or cyclopropyl.

[0088] In one embodiment, the present invention relates to compounds of formulas IA, IB and IC, in which the radicals L and R1 are as defined or preferably defined in the present application:

[0089] Preference is given to compounds of formula I, which are compiled in Tables 1 to 3 below, and which can be used in accordance with the invention.

TABLE 1

[0090] Compounds of formula I.A, where L and R1 for each individual compound correspond, in each case, to a line A-1 to A-72 of Table A (compounds I.A.A-1 to I.A.A-72). This means, for example, that a compound of formula I.A, where L is -C(=O)- and R1 is methyl (corresponding to definition A-49 in Table A) is called I.A.A-49.

TABLE 2

[0091] Compounds of formula I.B, where L and R1 for each individual compound correspond, in each case, to a line A-1 to A-72 of Table A (compounds I.B.A-1 to I.B.A-72).

TABLE 3

[0092] Compounds of formula IC, where L and R1 for each individual compound correspond, in each case, to a line A-1 to A-72 of Table A (compounds ICA-1 to ICA-72) TABLE A

[0093] It is understood that when in an aqueous medium, the compounds of formula I according to the invention may be present in a reversible equilibrium with the corresponding covalently hydrated forms in the CF3-oxadiazole motifs (i.e., the compounds of formula II and formula I-II, as shown below). This dynamic balance may be important for the biological activity of compounds of formula I. The designations of R1, R2, L, p, A, W, RA, n and RW with reference to compounds of formula I of the present invention apply generally to the compounds of Formula II and Formula I-II, such as the specific disclosures for the individual compounds disclosed in Tables 1 to 3, or the individual compounds disclosed in Tables C.1, C.2 and C.3 below.

[0094] Compounds of the present invention can be made as shown in the following schemes, in which, unless otherwise established, the definition of each variable is as defined above for a compound of formula I.

[0095] The compounds of formula I can be prepared according to the methods or in analogy with the methods that are described in the prior art. The synthesis takes advantage of starting materials that are commercially available or can be prepared according to conventional procedures, starting from readily available compounds.

[0096] For example, compounds of formula I can be prepared by reacting a compound of formula II, in which the nitrogen atom in group W is unsubstituted, with compounds of type III, for example, with a carboxylic acid chloride or anhydride , where LG is chlorine or carboxylate, in an organic solvent and in the presence of a base. Alternatively, compound I can be obtained by reacting compound II with the corresponding acid III, where LG is OH, using peptide coupling reaction conditions such as EDCI and HOBt (for precedents see, e.g., Bioorganic & Medicinal Chemistry Letters, 20(15), 4550-4554;

[0097] In one aspect, the invention relates to a process for preparing compounds of formula I, which comprises the process step of reacting a compound of formula II with compounds of type III, as described above, to result in compounds of formula I, and wherein the variables A, RA, W and RW are as defined or preferably defined in the present application for compounds of formula I.

[0098] Another embodiment of the invention relates to intermediate compounds of formula II, in which the variables A, RA, W and RW are as defined or preferably defined in the present application for compounds of formula I.

[0099] In one aspect, the invention relates to intermediate compounds of formula II.a

[00100] wherein the variables n, RA, W and RW are as defined or preferably defined in the present application for compounds of formula I; and in which the nitrogen atom in the W group is unsubstituted (the nitrogen atom carries a hydrogen). In a further embodiment, the invention relates to intermediate compounds of formulas II.a1, II.a2 and II.a3

[00101] Compounds II, in which the nitrogen atom in group W is unsubstituted, can be prepared from compounds of formula IV, in which the nitrogen atom in group W is protected by a suitable PG protecting group, e.g. , tert-butyloxycarbonyl. This can be achieved using acidic conditions (e.g. 3 M hydrochloric acid) at temperatures between 0°C and 100°C, in a suitable solvent.

[00102] Compounds of formula IV can be prepared by reacting type V amidines with trifluoroacetic anhydride in an organic solvent, preferably an ethereal solvent at temperatures between 0°C and 100°C, preferably at room temperature, as previously described in document WO 2013 /008162.

[00103] One skilled in the art will recognize that type V compounds can be accessed by treating type VI nitriles with hydroxylamine or its hydrochloride salt in organic solvent, such as methanol, at a temperature between 0°C and 100°C and in the presence of a base such as sodium carbonate (for precedents see, for example, WO 2009/074950, WO 2006/013104 and EP patent 1932843).

[00104] Compounds of formula VI, in which W is a 4-membered non-aromatic heterocycle that contains as ring member atoms in addition to carbon atoms, 1 nitrogen atom, can be prepared by catalyzed coupling of transition metals, which involves treating type VII boronic acids with a type VIII compound, where X is bromine or iodine. For precedents see, for example, WO 2013/053690, WO 2013/053690, WO 2015/095767.

[00105] Compounds of formula II, in which W is a 4-membered non-aromatic heterocycle that contains as ring member atoms in addition to carbon atoms, 1 nitrogen atom, can be prepared by epoxidation of the respective olefin of formula XII and subsequent replacement of oxygen by nitrogen using sodium azide and triphenylphosphine. Therefore, treating compounds of formula II with an oxidizing agent such as meta-chloroperoxybenzoic acid or tert-butyl hydroperoxide produces an oxirane (Journal of the American Chemical Society, 138(16), 5230-5233, 2016; European Journal of Organic Chemistry, (16), 2767-2773, 2008). This oxirane is then converted to aziridine using sodium azide and triphenylphosphine, as described in Journal of Organic Chemistry, 72(5), 2007, 1737-1741; Organic Letters, 12(17), 2010, 3772-3775.

[00106] Compounds of formula XII can be prepared by reacting amidines of type XIII in analogy to the procedure described above for the transformation of compound V to compound IV.

[00107] One skilled in the art will recognize that type XIII compounds can be accessed by treating type XIV nitriles in analogy to the procedure described above for the transformation of compound VI to compound V.

[00108] Alternatively, compounds of formula I can be prepared from compounds of formula XV in analogy to the procedure described above for the transformation of compound V to compound IV.

[00109] In one aspect, the invention relates to a process for preparing compounds of formula I, which comprises the process step of reacting a compound of formula XV with trifluoroacetic anhydride, to result in compounds of formula I, and in which the variables A, RA, W and RW, L, p, R1 and R2 are as defined or preferably defined in the present application for compounds of formula I.

[00110] Another embodiment of the invention relates to intermediate compounds of formula XV, in which the variables A, RA, W and RW, L, p, R1 and R2 are as defined or preferably defined in the present application for compounds of formula I .

[00111] In one aspect the invention relates to intermediate compounds of formula XV.a

[00112] wherein the variables RA, n, W, RW, L, p, R1 and R2 are as defined or preferably defined in the present application for compounds of formula I.

[00113] In a further embodiment, the invention relates to intermediate compounds of formulas XV.a1, XV.a2 and XV.a3,

[00114] AemA queA L,A p,A R1A andA R2A areA as definedA or preferably defined in the present application for compounds of formula I.

[00115] Preferably, the L group in compounds of formulas XV, XV.a, XV.a1, XV.a2 and Xv.a3 is -C(=O)-, -S(=O)2- or -C( =O) NH-.

[00116] In a further embodiment, the invention relates to intermediate compounds of formula XV.1a, where L is -C(=O)-, -S(=O)2- or - C(=O)NH -, and where R1 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2C6 alkynyl, C1-C6-alkoxyimino-C1-C4-alkyl, C2-C6-alkenyloxyimino-C1-C4-alkyl, C2-C6- alkynyloxyimino-C1-C4-alkyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, C3-C8-cycloalkyl-C1-C4-alkyl, phenyl-C1-C4-alkyl, heteroaryl-C1-C4-alkyl, phenyl, or a 5- or 6-membered aromatic heterocycle, wherein the ring member atoms of the aromatic heterocycle include in addition to carbon atoms 1, 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms with the proviso that the heterocycle cannot contain 2 contiguous atoms selected from O and S; and wherein the heteroaryl group in heteroaryl-C1-C4-alkyl is a 5- or 6-membered aromatic heterocycle, wherein the ring member atoms of the aromatic heterocycle include, in addition to carbon atoms, 1, 2, 3 or 4 selected heteroatoms from N, O and S as ring member atoms with the proviso that the heterocycle cannot contain 2 contiguous atoms selected from O and S; and wherein any of the aliphatic or cyclic groups R1 are unsubstituted or substituted by 1, 2, 3 or up to the maximum possible number of identical or different radicals selected from the group consisting of halogen, cyano, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy and C3-C8 cycloalkyl.

[00117] In a further embodiment, the invention relates to intermediate compounds of formula XV.1a, where L is -C(=O)-, -S(=O)2- or - C(=O)NH -; and wherein R1 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C3C6 alkynyl or C3-C11 cycloalkyl.

[00118] In a further embodiment, the invention relates to intermediate compounds of formula XV.1a, where L is -C(=O)-, -S(=O)2- or - C(=O)NH -; and wherein R1 is hydrogen, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl or cyclopropyl.

[00119] In a further embodiment, the invention relates to intermediate compounds of formula XV.2a, where L is -C(=O)-, -S(=O)2- or - C(=O)NH -, and where R1 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2C6 alkynyl, C1-C6-alkoxyimino-C1-C4-alkyl, C2-C6-alkenyloxyimino-C1-C4-alkyl, C2-C6- alkynyloxyimino-C1-C4-alkyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, C3-C8-cycloalkyl-C1-C4-alkyl, phenyl-C1-C4-alkyl, heteroaryl-C1-C4-alkyl, phenyl, or a 5- or 6-membered aromatic heterocycle, wherein the ring member atoms of the aromatic heterocycle include in addition to carbon atoms 1, 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms with the proviso that the heterocycle cannot contain 2 contiguous atoms selected from O and S; and wherein the heteroaryl group in heteroaryl-C1-C4-alkyl is a 5- or 6-membered aromatic heterocycle, wherein the ring member atoms of the aromatic heterocycle include, in addition to carbon atoms, 1, 2, 3 or 4 selected heteroatoms from N, O and S as ring member atoms with the proviso that the heterocycle cannot contain 2 contiguous atoms selected from O and S; and wherein any of the aliphatic or cyclic groups R1 are unsubstituted or substituted by 1, 2, 3 or up to the maximum possible number of identical or different radicals selected from the group consisting of halogen, cyano, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy and C3-C8 cycloalkyl.

[00120] In a further embodiment, the invention relates to intermediate compounds of formula XV.2a, where L is -C(=O)-, -S(=O)2- or - C(=O)NH -; and wherein R1 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C3C6 alkynyl or C3-C11 cycloalkyl.

[00121] In a further embodiment, the invention relates to intermediate compounds of formula XV.2a, where L is -C(=O)-, -S(=O)2- or - C(=O)NH -; and wherein R1 is hydrogen, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl or cyclopropyl.

[00122] In a further embodiment, the invention relates to intermediate compounds of formula XV.3a, where L is -C(=O)-, -S(=O)2- or - C(=O)NH -, and where R1 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2C6 alkynyl, C1-C6-alkoxyimino-C1-C4-alkyl, C2-C6-alkenyloxyimino-C1-C4-alkyl, C2-C6- alkynyloxyimino-C1-C4-alkyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, C3-C8-cycloalkyl-C1-C4-alkyl, phenyl-C1-C4-alkyl, heteroaryl-C1-C4-alkyl, phenyl, or a 5- or 6-membered aromatic heterocycle, wherein the ring member atoms of the aromatic heterocycle include in addition to carbon atoms 1, 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms with the proviso that the heterocycle cannot contain 2 contiguous atoms selected from O and S; and wherein the heteroaryl group in heteroaryl-C1-C4-alkyl is a 5- or 6-membered aromatic heterocycle, wherein the ring member atoms of the aromatic heterocycle include, in addition to carbon atoms, 1, 2, 3 or 4 selected heteroatoms from N, O and S as ring member atoms with the proviso that the heterocycle cannot contain 2 contiguous atoms selected from O and S; and wherein any of the aliphatic or cyclic groups R1 are unsubstituted or substituted by 1, 2, 3 or up to the maximum possible number of identical or different radicals selected from the group consisting of halogen, cyano, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy and C3-C8 cycloalkyl.

[00123] In a further embodiment, the invention relates to intermediate compounds of formula XV.3a, where L is -C(=O)-, -S(=O)2- or - C(=O)NH -; and wherein R1 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C3C6 alkynyl or C3-C11 cycloalkyl.

[00124] In a further embodiment, the invention relates to intermediate compounds of formula XV.3a, where L is -C(=O)-, -S(=O)2- or - C(=O)NH -; and wherein R1 is hydrogen, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl or cyclopropyl.

[00125] Particularly preferred examples of intermediates are compounds of formula XV.a1, especially compounds XV.a1.A-1 to XV.a1.A-72, in which the meaning of the radicals L and R1 for each individual compound corresponds, in each case, to a line A-1 to A-72 of Table A.

[00126] Particularly preferred examples of intermediates are compounds of formula XV.a2, especially compounds XV.a2.A-1 to XV.a2.A-72, in which the meaning of the radicals L and R1 for each individual compound corresponds, in each case, to a line A-1 to A-72 of Table A.

[00127] Particularly preferred examples of intermediates are compounds of formula XV.a3, especially compounds XV.a3.A-1 to XV.a3.A-72, in which the meaning of the radicals L and R1 for each individual compound corresponds, in each case, to a line A-1 to A-72 of Table A.

[00128] Compounds of formula XV can be prepared from compounds of formula XVI in analogy to the procedure described above for the transformation of compound VI to compound V.

[00129] Compounds of formula XVI can be prepared by reacting compound of type XVII in analogy to the procedure described above for the transformation of compound II to compound I.

[00130] Compounds of formula XVII can be prepared from compounds of formula VI in analogy to the procedure described above for the transformation of compound IV to compound II.

[00131] Compounds XVII can be prepared from compounds of formula XVIIII in analogy to the procedure described above for the transformation of compound IV to compound or procedure described for the transformation of compound VII to compound VI.

[00132] Compounds of formula VII, XIV and XVIII are commercially available.

[00133] Compounds I and the compositions according to the invention are particularly important in controlling a large amount of phytopathogenic fungi in various cultivated plants, such as cereals, for example, wheat, rye, barley, triticale, oats or rice; beetroot, e.g. sugar beetroot or fodder beetroot; fruits, such as pome fruits, drupes or soft fruits, for example apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries, blackberries or currants; legume plants, such as lentils, peas, alfalfa or soybeans; oil plants such as rapeseed, mustard, olive, sunflower, coconut, cocoa beans, castor oil, palm oil, nuts or soybeans; cucurbits, such as pumpkins, cucumbers and melons; fibrous plants such as cotton, flax, hemp or jute; citrus fruits, such as oranges, lemons, grapefruits or mandarins; vegetables, such as spinach, lettuce, asparagus, cabbage, carrots, onions, tomatoes, potatoes, cucurbits or paprika; laurel plants, such as avocados, cinnamon or camphor; plants for generating energy and raw materials, such as corn, soybeans, rapeseed, sugar cane or palm oil; corn, tobacco; nuts; coffee; tea; bananas; vines (table grapes and juice grape vines); hop; peat, sweet leaf (also called Stevia); natural rubber plants or ornamental and forestry plants such as flowers, shrubs, broad-leaved or evergreen trees, e.g. conifers; and on plant propagation material, such as seeds, and the culture material of these plants.

[00134] Preferably, compounds I and compositions thereof, respectively are used to control a variety of fungi in field crops, such as potatoes, sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans , rapeseed, legumes, sunflower, coffee or sugar cane; fruits; vines; ornamental plants; or vegetables, such as cucumbers, tomatoes, beans or pumpkin.

[00135] The term “plant propagation material” should be understood as denoting all generative parts of the plant such as seeds and vegetative plant material such as cuttings and tubers (e.g. potatoes), which can be used for multiplication of the plant . This includes seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, corms and other parts of plants, including seedlings and young plants, which will be transplanted after germination or after emergence from the soil. These young plants can also be protected before transplanting by full or partial treatment, by soaking or pouring.

[00136] Preferably, the treatment of plant propagation materials with compounds I and compositions thereof, respectively, is used to control a large number of fungi in cereals, such as wheat, rye, barley and oats; rice, corn, cotton and soybeans.

[00137] The term “cultivated plants” should be understood as including plants that have been modified by mutagenesis or genetic engineering in order to provide a new trait for a plant or to modify an already present trait.

[00138] Mutagenesis includes random mutagenesis techniques using X-rays or mutagenic chemicals, but also targeted mutagenesis techniques, to create mutations at a specific locus of a plant genome. Targeted mutagenesis techniques often use oligonucleotides or CRISPR/Cas-like proteins, zinc finger nucleases, TALENs, or meganucleases to achieve the targeting effect. Genetic engineering generally uses recombinant DNA techniques to create modifications to a plant's genome that under natural circumstances cannot be easily obtained by breeding, mutagenesis, or natural recombination. Typically, one or more genes are integrated into a plant's genome to add a trait or improve a trait. These integrated genes are also referred to as transgenes in the art, while the plant comprising these transgenes are referred to as transgenic plants. The process of plant transformation generally produces several transformation events, which differ in the genomic locus at which a transgene has been integrated. Plants that comprise a specific transgene at a specific genomic locus are generally described as comprising a specific “event”, which is referred to by a specific event name. Traits that have been introduced into plants or have been modified include herbicide tolerance, insect resistance, yield, and increased tolerance to abiotic conditions such as aridity.

[00139] Herbicide tolerance has been created through the use of mutagenesis, as well as through the use of genetic engineering. Plants that have become tolerant to acetolactate synthetase (ALS) inhibitor herbicides through mutagenesis and breeding comprise varieties commercially available under the name Clearfield®.

[00140] Herbicide tolerance has been created through the use of transgenes for glyphosate, glufosinate, 2,4-D, dicamba, oxynyl herbicides such as bromoxynil and ioxynil, sulfonylurea herbicides, ALS inhibitors and 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors ), such as isoxaflutole and mesotrione.

[00141] Transgenes that have been used to provide herbicide tolerance traits comprise: for glyphosate tolerance: cp4 epsps, epsps grg23ace5, mepsps, 2mepsps, gat4601, gat4621, goxv247; for glufosinate tolerance: pat and bar, for 2,4-D tolerance: aad-1, aad-12; for dicamba tolerance: dmo; for tolerance to oxynil herbicides: bxn; for tolerance to sulfonylurea herbicides: zm-hra, csr1-2, gm-hra, S4-HrA; for tolerance to ALS inhibitors: csr1-2; and for tolerance to HPPD inhibitors: hppdPF, W336, avhppd-03.

[00142] Corn transgenic events comprising herbicide tolerance genes include, but are not limited to, DAS40278, MON801, MON802, MON809, MON810, MON832, MON87411, MON87419, MON87427, MON88017, MON89034, NK603, GA21, HG0JG, HCEM485, VCO-01981-5, 676, 678, 680, 33121, 4114, 59122, 98140, Bt10, Bt176, CBH-351, DBT418, DLL25, MS3, MS6, MZIR098, T25, TC1507 and TC6275.

[00143] Soybean transgenic events comprising herbicide tolerance genes include, but are not limited to, GTS 40-3-2, MON87705, MON87708, MON87712, MON87769, MON89788, A2704-12, A2704-21, A5547-127 , A5547-35, DP356043, DAS44406-6, DAS68416-4, DAS-81419-2, GU262, SYHT0H2, W62, W98, FG72 and CV127.

[00144] Soybean transgenic events comprising herbicide tolerance genes include, but are not limited to, 19-51a, 31707, 42317, 81910, 281-24-236, 3006-210-23, BXN10211, BXN10215, BXN10222, BXN10224, MON1445, MON1698, MON88701, MON88913, GHB119, GHB614, LLCotton25, T303-3 and T304-40.

[00145] Canola transgenic events comprising herbicide tolerance genes are, for example, but do not exclude others, MON88302, HCR-1, HCN10, HCN28, HCN92, MS1, MS8, PHY14, PHY23, PHY35, PHY36, RF1, RF2 and RF3.

[00146] Insect resistance was created mainly by transferring genes from bacteria for insecticidal proteins to plants: Transgenes that have been most frequently used are toxin genes from Bacillus spp. and synthetic variants thereof, such as cry1A, cry1Ab, cry1Ab-Ac, cry1Ac, cry1A.105, cry1F, cry1Fa2, cry2Ab2, cry2Ae, mcry3A, ecry3.1Ab, cry3Bb1, cry34Ab1, cry35Ab1, cry9C, vip3A(a), vip3Aa20. However, also genes of plant origin, such as genes encoding protease inhibitors such as CpTI and pinII, have been transferred to other plants. An additional approach uses transgenes such as dvsnf7 to produce double-stranded RNA in plants.

[00147] Corn transgenic events comprising genes for insecticidal proteins or double-stranded RNA include, but are not limited to, Bt10, Bt11, Bt176, MON801, MON802, MON809, MON810, MON863, MON87411, MON88017, MON89034, 33121, 4114, 5307, 59122, TC1507, TC6275, CBH-351, MIR162, DBT418 and MZIR098. Corn transgenic events that comprise genes for insecticidal proteins include, but are not limited to, MON87701, MON87751, and DAS-81419. Corn transgenic events comprising genes for insecticidal proteins include, but are not limited to, SGK321, MON531, MON757, MON1076, MON15985, 31707, 31803, 31807, 31808, 42317, BNLA-601, Event1, COT67B, COT102, 3, T304-40, GFM Cry1A, GK12, MLS 9124, 281-24-236, 3006-210-23, GHB119 and SGK321.

[00148] Increased production was created with the use of the athb17 transgene, being present, for example, in the corn event MON87403, or with the use of the bbx32 transgene, being present, for example, in the soybean event MON87712.

[00149] Cultivated plants comprising a modified oil content were created using the transgenes: gm-fad2-1, Pj.D6D, Nc.Fad3, fad2-1A and fatb1-A. Soybean events that comprise at least one of these genes are: 260-05, MON87705 and MON87769.

[00150] Tolerance to abiotic conditions, such as aridity, was created through the use of the cspB transgene, comprised by the corn event MON87460, and through the use of the Hahb-4 transgene, comprised by the soybean event IND-00410-5.

[00151] Traits are often combined by combining genes in a transformation event or by combining different events during the breeding process, resulting in a crop plant with stacked traits. Preferred trait combinations are combinations of herbicide tolerance traits for different groups of herbicides, combinations of insect tolerance for different types of insects, in particular tolerance to lepidopteran and coleopteran insects, combinations of herbicide tolerance with one or more types of resistance to insects, combinations of herbicide tolerance with increased production, as well as combinations of herbicide tolerance and tolerance to abiotic conditions.

[00152] Plants that comprise single or stacked traits, as well as the genes and events that provide these traits are well known in the art. For example, detailed information about mutagenized or integrated genes and the respective events is available on the websites of the organizations “International Service for the Acquisition of Agribiotech Applications (ISAAA)” (http://www.isaaa.org/gmapprovaldatabase) and the “ Center for Environmental Risk Assessment (CERA)” (http://ceragmc.org/GMCropDatabase). Additional information on the specific events and methods for detecting them can be found for canola events MS1, MS8, RF3, GT73, MON88302, KK179 in documents WO 01/031042, WO 01/041558, WO 01/041558, WO 02/036831 , WO 11/153186, WO 13/003558, for cotton events MON1445, MON15985, MON531 (MON15985), LLCotton25, MON88913, COT102, 281-24-236, 3006-210-23, COT67B, GHB614, 0, GHB119, MON88701, 81910 in WO 02/034946, WO 02/100163, WO 02/100163, WO 03/013224, WO 04/072235, WO 04/039986, WO 05/103266, WO 05/1032 66, WO 06/ 128573, WO 07/017186, WO 08/122406, WO 08/151780, WO 12/134808, WO 13/112527; for corn events GA21, MON810, DLL25, TC1507, MON863, MIR604, LY038, MON88017, 3272, 59122, NK603, MIR162, MON89034, 98140, 32138, MON87460, 5307, MON874, 27, DAS40278, MON87411, 33121, MON87403, MON87419 in WO 98/044140, US patents 02/102582, US 03/126634, WO 04/099447, WO 04/011601, WO 05/103301, WO 05/061720, WO 05/059103, WO 06/0989 52, WO 06/039376, US Pat. 1/ 062904, WO 11/022469, WO 13/169923, WO 14/116854, WO 15/053998, WO 15/142571; for potato events E12, F10, J3, J55, V11, 17/062825; for rice events LLRICE06, LLRICE601, LLRICE62 in documents WO 00/026345, WO 00/026356, WO 00/026345; and for soybean events H7-1, MON89788, A2704- 12, A5547-127, DP305423, DP356043, MON87701, MON87769, CV127, MON87705, DAS68416-4, MON87708, MON87712, SYHT0H2, DAS81419 x DAS44406-6, MON87751 in WO 04/074492, WO 06/130436, WO 06/108674, WO 06/108675, WO 08/054747, WO 08/002872, WO 09/064652, WO 09/102873, WO 10/080829, WO 10 / 037016, WO 11/066384, WO 11/034704, WO 12/051199, WO 12/082548, WO 13/016527, WO 13/016516, WO 14/201235.

[00153] The use of compounds I and compositions according to the invention, respectively, in cultivated plants can result in effects that are specific to a cultivated plant that comprises a certain gene or event. These effects may involve changes in growth behavior or altered resistance to biotic or abiotic stress factors. These effects may comprise, in particular, improved production, improved resistance or tolerance to insects, nematodes, fungi, bacteria, mycoplasma, viruses or viroid pathogens, as well as initial vigor, early or delayed ripening, tolerance to cold or heat, as well as amino acids. or altered spectrum or fatty acid content.

[00154] Compounds I and compositions thereof, respectively, are particularly suitable for controlling the following diseases in plants:

[00155] Albugo spp. (White rust) on ornamental plants, vegetables (e.g. A. candida) and sunflowers (e.g. A. tragopogonis); Alternaria spp. (Alternaria leaf spot) on vegetables (e.g. A. dauci or A. porri), rapeseed (A. brassicicola or brassicae), sugar beet (A. tenuis), fruit (e.g. A. grandis), rice, soybeans, potatoes and tomatoes (e.g. A. solani, A. grandis or A. alternata), tomatoes (e.g. A. solani or A. alternata) and wheat (e.g. A. triticina); Aphanomyces spp. in sugar beet and vegetables; Ascochyta spp. in cereals and vegetables, for example, A. tritici (anthracnose) in wheat and A. hordei in barley; Aureobasidium zeae (syn. Kapatiella zeae) in corn; Bipolaris and Drechslera spp. (teleomorph: Cochliobolus spp.), e.g. Southern leaf blight (D. maydis) or Northern leaf blight (B. zeicola) on maize, e.g. leaf spot (B. sorokiniana) on cereals and e.g. B. oryzae in rice and peat; Blumeria (formerly Erysiphe) graminis (powdery mildew) on cereals (e.g. on wheat or barley); Botrytis cinerea (teleomorph: Botryotinia fuckeliana: gray mold) on fruits and berries (e.g. strawberries), vegetables (e.g. lettuce, carrots, celery and cabbage); B. squamosa or B. allii in the carrot family), rapeseed, ornamentals (e.g. B eliptica), vines, forestry plants and wheat; Bremia lactucae (powdery mildew) on lettuce; Ceratocystis (syn. Ophiostoma) spp. (rot or decay) on broad-leaved, evergreen trees, e.g. C. ulmi (Dutch elm disease) on elms; Cercospora spp. (Cercospora leaf spot) on corn (e.g. gray leaf spot: C. zeae-maydis), rice, sugar beet (e.g. C. beticola), sugar cane, vegetables, coffee, soybeans (e.g. , C. sojina or C. kikuchii) and rice; Cladobotryum (syn. Dactylium) spp. (e.g. C. mycophilum (formerly Dactylium dendroides, teleomorph: Nectria albertinii, Nectria rosella syn. Hypomyces rosellus) in mushrooms; Cladosporium spp. in tomatoes (e.g. C. fulvum: leaf mold) and cereals, e.g. C. herbarum (black ear) in wheat; Claviceps purpurea (rye spur) in cereals; Cochliobolus (anamorph: Bipolaris Helminthosporium) spp. , anamorph: B. sorokiniana) and rice (e.g. C. miyabeanus, anamorph: H. oryzae); Colletotrichum (teleomorph: Glomerella) spp. , C. graminicola: Anthracnose stalk rot), soft fruits, potatoes (e.g. C. coccodes: black sclerotia), beans (e.g. C. lindemuthianum), soybeans (e.g. C. truncatum or C. gloeosporioides) , vegetables (e.g., C. lagenarium or C. capsici), fruits (e.g., C. acutatum), coffee (e.g., C. coffeanum or C. kahawae) and C. gloeosporioides in various crops; Corticium spp., e.g. C. sasakii (sheath disease) in rice; Corynespora cassiicola (leaf spots) on soybeans and ornamental plants; Cycloconium spp., e. g. C. oleaginum on olive trees; Cylindrocarpon spp. (e.g., fruit tree canker or young vine decline, teleomorph: Nectria or Neonectria spp.) on fruit trees, grapevines (e.g., C. liriodendri, teleomorph: Neonectria liriodendri: Black Foot Disease), and ornamentals; Dematophora (teleomorph: Rosellinia) necatrix (root and stem rot) in soybeans; Diaporthe spp., e.g., D. phaseolorum (damping off) in soybeans; Drechslera (syn. Helminthosporium, teleomorph: Pyrenophora) spp. in maize, cereals such as barley (e.g. D. teres, net spot) and wheat (e.g. D. tritici-repentis: yellow spot), rice and peat; Esca (death, apoplexy) in grapevines, caused by Formitiporia (syn. Phellinus) punctata, F. mediterranea, Phaeomoniella chlamydospora (formerly Phaeoacremonium chlamydosporum), Phaeoacremonium aleophilum and/or Botryosphaeria obtusa; Elsinoe spp. in pome fruit (E. pyri), fragile fruits (E. veneta: anthracnose) and vines (E. ampelina: anthracnose); Entyloma oryzae (leaf spot) on rice; Epicoccum spp. (black mold) on wheat; Erysiphe spp. (powdery mildew) on sugar beet (E. betae), vegetables (e.g. E. pisi) such as cucurbits (e.g. E. cichoracearum), cabbage, rapeseed (e.g. E. cruciferarum); Eutypa lata (Eutypa canker or dieback, anamorph: Cytosporina lata, syn. Libertella blepharis) on fruit trees, vines and ornamental woodlands; Exserohilum (syn. Helminthosporium) spp. in corn (e.g. E. turcicum); Fusarium (teleomorph: Gibberella) spp (wilt, root or stem rot) on various plants, such as F. graminearum or F. culmorum (root rot, scar or Fusarium head blight) on cereals (e.g. wheat or barley), F. oxysporum in tomatoes, F. solani (f. sp. Glycines now syn. F. virguliforme), and F. tucumaniae and F. brasiliense each causing sudden death syndrome in soybeans and F. verticillioides in corn; Gaeumannomyces graminis (takes everything) in cereals (e.g. wheat or barley) and maize; Gibberella spp in cereals (e.g. G. zeae) and rice (e.g. G. fujikuroi: Bakanae disease); Glomerella cingulata on vines, pome fruits and other plants and G. gossypii on cotton; grain coloring in rice complex; Guignardia bidwellii (black rot) on grapevines; Gymnosporangium spp on rosaceous plants and junipers, e.g. G. sabinae (rust) on pears; Helminthosporium spp (syn. Drechslera, teleomorph: Cochliobolus) in corn, cereals, potatoes and rice; Hemileia spp, e.g. H. uvatrix (coffee leaf rust) in coffee; Isariopsis clavispora (syn. Cladosporium vitis) on vines; Macrophomina phaseolina (syn. phaseoli) (root and stem rot) in soybeans and cotton; Microdochium (syn. Fusarium) nivale (pink snowspot) in cereals (e.g. wheat or barley); Microsphaera diffusa (powdery mildew) on soybeans; Monilinia spp., e.g. M. laxa, M. fructicola and M. fructigena (syn. Monilia spp.: flowering and twig blight, brown rot) on drupes and other rosaceous plants; Mycosphaerella spp. in cereals, bananas, soft fruits and dried fruits, such as M. graminicola (anamorph: Zymoseptoria tritici formerly Septoria tritici: Septoria blotch) in wheat or M. fijiensis (syn. Pseudocercospora fijiensis: black Sigatoka disease) and M. musicola on bananas, M. arachidicola (syn. M. arachidis or Cercospora arachidis), M. berkeleyi on peanuts, M. pisi on pears, and M. brassiciola on brassicas; Peronospora spp. (powdery mildew) on cabbage (e.g. P. brassicae), rapeseed (e.g. P. parasitica), onions (e.g. P. destructor), tobacco (P. tabacina) and soybeans (e.g. P. manshurica ); Phakopsora pachyrhizi and P. meibomiae (soybean rust) in soybeans; Phialophora spp. for example, in grapevines (e.g. P. tracheiphila and P. tetraspora) and soybeans (e.g. P. gregata: stem rot); Phoma lingam (syn. Leptosphaeria biglobosa and L. maculans: root and stem rot) in rapeseed and cabbage, P. betae (root rot, leaf spot and damping-off) in sugar beet and P. zeae- maydis (syn. Phyllostica zeae) in corn; Phomopsis spp. in sunflowers, grapevines (e.g. P. viticola: can and leaf spot) and soybeans (e.g. stem rot: P. phaseoli, teleomorph: Diaporthe phaseolorum); Physoderma maydis (brown spots) on corn; Phytophthora spp (rot, root, leaf, fruit and stem rot) on various plants such as paprika and cucurbits (e.g. P. capsici), soybeans (e.g. P. megasperma, syn. P.syiae), potatoes and tomatoes (e.g. P. infestans: late blight) and broadleaf trees (e.g. P. ramorum: sudden oak death); Plasmodiophora brassicae (hernia) on cabbage, rapeseed, radish and other plants; Plasmopara spp, e.g. P. viticola (vine powdery mildew) on grapevines and P. halstedii on sunflowers; Podosphaera spp. (powdery mildew) on rosacea plants, hops, pome fruits and soft fruits, (for example, P. leucotricha on apples) and curcubits; P. xanthii); Polymyxa spp., for example, in cereals such as wheat and barley (P. graminis) and sugar beet (P. betae) and through this transmitted viral diseases; Pseudocercosporella herpotrichoides (syn. Oculimacula yallundae, O. acuformis: eye spot, teleomorph: Tapesia yallundae) in cereals, e.g. wheat or barley; Pseudoperonospora (powdery mildew) on various plants, e.g. P. cubensis on cucurbits or P. humili on hops; Pseudopezicula tracheiphila (red fire disease or ‘rotbrenner’, anamorph: Phialophora) on grapevines; Puccinia spp. (rusts) on various plants, e.g. P. triticina (brown or leaf rust), P. striiformis (striped or yellow rust), P. hordei (dwarf rust), P. graminis (stem or black rust) or P. . recondita (brown or leaf rust) on cereals, such as wheat, barley or rye, P. kuehnii (orange rust) on sugar cane and P. asparagi on asparagus; Pyrenopeziza spp., e.g. P. brassicae in rapeseed; Anamorphic Pyrenophora: Drechslera) tritici-repentis (yellow spot - tan spot) on wheat or P. teres (net spot) on barley; Pyricularia spp., e.g. P. oryzae (teleomorph: Magnaporthe grisea: rice blast) in rice and P. grisea in peat and cereals; Pythium spp. (damping off) in peat, rice, corn, wheat, cotton, rapeseed, sunflower, soybeans, sugar beets, vegetables and various other plants (e.g. P. ultimum or P. aphanidermatum) and P. oligandrum in mushrooms; Ramularia spp., e.g. R. collo-cygni (Ramularia leaf spots, Physiological leaf spots) in barley and R. beticola in sugar beet; Rhizoctonia spp. on cotton, rice, potatoes, peat, corn, rapeseed, potatoes, sugar beets, vegetables and various other plants, e.g. R. solani (root and stem rot) on soybeans, R. solani (sheath blight) on rice or R. cerealis (Rhizoctonia shoot blight) on wheat or barley; Rhizopus stolonifer (black mold, soft rot) on strawberries, carrots, cabbage, grapevines and tomatoes; Rhynchosporium secalis (scorch) on barley, rice and triticale; Sarocladium oryzae and S. attenuatum (sheath rot) in rice; Sclerotinia spp. (stem rot or white mold) on vegetables (S. minor and S. sclerotiorum) and field crops such as rapeseed, sunflowers (e.g. S. sclerotiorum) and soybeans S. rolfsii (syn. Athelia rolfsii) on soybeans, peanuts, vegetables, corn, cereals and ornamental plants; Septoria spp. In several plants, for example, S. glycines (brown spot) in soybeans, S. tritici (syn. Zymoseptoria tritici, Septoria blotch) in wheat, and S. (syn. Stagonospora) nodorum (glume spot) in cereals; Uncinula (syn. Erysiphe) necator (powdery downy mildew, anamorph: Oidium tuckeri) on grapevines; Setosphaeria spp. (leaf wilt) in corn (e.g. S. turcicum, syn. Helminthosporium turcicum) and peat; Sphacelotheca spp. (charcoal) in corn, (e.g. S. reiliana, syn. Ustilago reiliana: tassel charcoal), sorghum and sugar cane; Sphaerotheca fuliginea (syn. Podosphaera xanthii: powdery mildew) on cucurbits; Spongospora subterranea (powdery scab) on potatoes and viral diseases thus transmitted; Stagonospora spp. In cereals, for example, S. nodorum (Stagonospora blotch, teleomorph: Leptosphaeria (syn. Phaeosphaeria) nodorum, syn. Septoria nodorum) in wheat; Synchytrium endobioticum on potatoes (potato wart disease); Taphrina spp., e.g. T. deformans (curled leaf disease) in peaches T. pruni (plum pocket) in plums; Thielaviopsis spp. (black root rot) on tobacco, pome fruits, vegetables, soybeans and cotton, e.g. T. basicola (syn. Chalara elegans); Tilletia spp. (grain smut or fetid smut) in cereals, such as T. tritici (syn. T. caries, wheat decay) and T. controversial (dwarf bunt) in wheat; Trichoderma harzianum in mushrooms; Typhula incarnata (gray snow mold) on barley or wheat; Urocystis spp., e.g., U. occulta (stem smut) in rye; Uromyces spp. (rust) in vegetables, such as beans (e.g., U. appendiculatus, syn. U. phaseoli), sugar beets (e.g., U. betae or U. beticola) and in pulses (e.g., U. vignae, U. pisi, U. viciae-fabae and U. fabae); Ustilago spp. (loose smut) in cereals (e.g., U. nuda and U. avaenae), corn (e.g., U. maydis: corn smut), and sugar cane; Venturia spp. (scab) on apples (e.g. V. inaequalis) and pears; and Verticillium spp. (rot) in various plants such as fruit and ornamental plants, vines, soft fruits, vegetables and field crops, e.g. V. longisporum in rapeseed, V. dahliae in moragos, rapeseed, potatoes and tomatoes, and V. fungicola in mushrooms; Zymoseptoria tritici in cereals.

[00156] In a preferred embodiment, compounds I, mixtures thereof with other active compounds as defined in the present application and compositions thereof, respectively, are particularly suitable for controlling the following diseases in plants: Puccinia spp. (rusts) on various plants, for example, but not limited to P. triticina (brown and leaf rust), P. striiformis (linear or yellow rust), P. hordei (dwarf rust), P. graminis (rust) stem or black) or P. recondita (brown or leaf rust) on cereals such as wheat, barley or rye, P. sorghi (common rust) on maize, P. polysora (corn rust) on maize; P. coronata for example, in oats, P. sorghi and P. polysora in corn; Puccinia spp. In other crops, for example, P. heliathi in sunflower, P. arachidis in peanut; Uromyces spp. In pulses and other cultures, for example, Uromyces viciae-fabae, Uromyces vigniae, Uromyces pisi, U. ciceris-arietini, U. betae sin U. beticola; ePhakopsoraceae spp. on several plants, in particular Phakopsora pachyrhizi and P. meibomiae (soybean rust) on soybeans.

[00157] Compounds I and compositions thereof, respectively, are also suitable for controlling harmful fungi in protecting stored products or harvesting and protecting materials.

[00158] The term “materials protection” should be understood as denoting the protection of non-living techniques and materials, such as adhesives, glues, wood, paper and cardboard, textiles, leather, paint dispersions, plastics, refrigeration lubricants, fiber or fabrics, against infestation and destruction by harmful microorganisms, such as fungi and bacteria. Regarding the protection of wood and other materials, specific attention is given to the following harmful fungi: Ascomycetes such as Ophiostoma spp., Ceratocystis spp., Aureobasidium pullulans, Sclerophoma spp., Chaetomium spp., Humicola spp., Petriella spp., Trichurus spp. .; Basidiomycetes such as Coniophora spp., Coriolus spp., Gloeophyllum spp., Lentinus spp., Pleurotus spp., Poria spp., Serpula spp. and Tyromyces spp., Deuteromycetes such as Aspergillus spp., Cladosporium spp., Penicillium spp., Trichoderma spp., Alternaria spp., Paecilomyces spp. and Zygomycetes such as Mucor spp., and furthermore in the protection of stored products and harvesting the following yeast fungi are worthy of note: Candida spp. and Saccharomyces cerevisae.

[00159] The treatment method according to the invention can also be used in the field of protecting products or stored crops against attack by fungi and microorganisms. According to the present invention, the term “stored products” is understood to denote natural substances of plant or animal origin and their processed forms, which have been taken from the natural life cycle and for which long-term protection is desired. . Stored products of vegetable crop origin, such as plants or parts thereof, e.g. stalks, leaves, tubers, seeds, fruits or grains, may be protected in the freshly harvested state or in the processed form, such as pre-dried, moistened , crushed, ground, pressed or roasted, the process of which is also known as post-harvest treatment. Also covered by the definition of stored products are wood products, in the form of raw wood, such as construction lumber, electricity poles and barriers, or in the form of finished articles, such as furniture or objects made of wood. Stored products of animal origin are bovine hide, leather, skin, hair and similar products. Combinations according to the present invention can avoid unfavorable effects such as decomposition, discoloration or fungus. Preferably, “stored products” is understood to denote natural substances of plant origin and their processed forms, most preferably fruits and their processed forms, such as pome fruits, drupes, soft fruits and citrus fruits, and their processed forms.

[00160] Compounds I and compositions thereof, respectively, can be used to improve the health of a plant. The invention also relates to a method for improving plant health by treating a plant, propagation material and/or place where the plant is growing or will grow, with an effective amount of compounds I and compositions thereof, respectively.

[00161] The term “phytosanitary” should be understood as denoting a condition of the plant and/or its products, which is determined by several indicators, alone or in combination with each other, such as production (for example, increased biomass and/or content of valuable ingredients), plant vigor (e.g. improved plant growth and/or greener leaves (“greening effect”)), quality (e.g. improved content or composition of certain ingredients) and abiotic stress tolerance and/or biotic. The indicators identified above for a plant's health condition may be interdependent, or they may result from each other.

[00162] Compounds of formula I may be present in different crystalline modifications whose biological activity may differ. They are, likewise, subject matter of the present invention.

[00163] Compounds I are employed as such or in the form of compositions to treat fungi or plants, plant propagation materials such as seeds, soil, surfaces, materials or spaces to be protected against fungal attack with an amount fungicidal effect of the active substances. Application can be carried out before and after fungal infection in plants, plant propagation materials such as seeds, soil, surfaces, materials or spaces.

[00164] Plant propagation materials can be treated with compounds I as such or a composition comprising at least one compound I prophylactically, both before and at planting or transplanting.

[00165] The invention also relates to agrochemical compositions comprising an auxiliary and at least one compound I according to the invention.

[00166] An agrochemical composition comprises a fungicidally effective amount of a compound I. The term “effective amount” denotes an amount of the composition or compounds I, which is sufficient to control plants harmful fungi in cultivated plants or in the protection of materials, and which does not result in substantial damage to the treated plants. This amount can vary over a wide range and is dependent on several factors, such as the fungal species to be controlled, the plant or cultivated material treated, the climatic conditions and the specific compound used.

[00167] Compounds I, their N-oxides and salts can be converted into common types of agrochemical compositions, for example, solutions, emulsions, suspensions, sprays, powders, pastes, granules, presses, capsules and mixtures thereof. Examples of composition types are suspensions (e.g., SC, OD, FS), emulsifiable concentrates, (e.g., EC), emulsions (e.g., EW, EO, ES, ME), capsules (e.g., CS, ZC ), pastes, tablets, wettable powders or powders (e.g. WP, SP, WS, DP, DS), pressed (e.g. BR, TB, DT), granules (e.g. WG, SG, GR, FG, GG, MG), insecticidal articles (e.g. LN), as well as gel formulations for the treatment of plant propagation materials such as seeds (e.g. GF). These and other types of additional compositions are defined in the “Catalogue of pesticide formulation types and international coding system”, Technical Monograph n° 2, 6th Ed. May 2008, CropLife International.

[00168] The compositions are prepared in a known manner, as described by Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005.

[00169] Suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetting agents, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, stimulants. food, compatibilizers, bactericides, anti-freezing agents, anti-foam agents, dyes, stickiness enhancers and binders.

[00170] Suitable solvents and liquid carriers are water and organic solvents, such as mineral oil fractions of medium to high boiling point, for example, kerosene, diesel oil and oils of vegetable or animal origin; cyclic and aromatic hydrocarbons, for example, toluene, paraffin, tetrahydronaphthalene, alkylated naphthalenes; alcohols, for example, ethanol, propanol, butanol, benzyl alcohol, cyclohexanol; glycols; DMSO; ketones, e.g. cyclohexanone; esters, for example lactates, carbonates, fatty acid esters, gamma-butyrolactone, fatty acids; phosphonates; amines; amides, for example, N-methyl pyrrolidone, dimethylamides of fatty acids; and mixtures thereof.

[00171] Suitable solid carriers or fillers are earth minerals, for example, silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide ; polysaccharides, e.g. cellulose, starch; fertilizers, e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, for example, cereal flour, wood flour, walnut shell flour, and mixtures thereof.

[00172] Suitable surfactants are surface active compounds, such as anionic, cationic, non-ionic and amphoteric surfactants, block polymers, polyelectrolytes and mixtures thereof. These surfactants can be used as emulsifiers, dispersants, solubilizers, wetting agents, penetration enhancers, protective colloids or adjuvants. Examples of surfactants are listed in McCutcheon’s, Vol.1: Emulsifiers & Detergents, McCutcheon’s Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).

[00173] Suitable anionic surfactants are alkali or alkaline earth metals, ammonium sulfonate salts, sulfates, phosphates, carboxylates and mixtures thereof. Examples of sulfonates are alkylaryl sulfonates, diphenyl sulfonates, alpha-olefin sulfonates, lignin sulfonates, sulfonates of fatty acids and oils, ethoxylated alkylphenol sulfonates, alkoxylated arylphenol sulfonates, condensed naphthalene sulfonates, dodecyl and tridecylbenzene sulfonates, naphthalene sulfonates and alkyl naphthalenes, sulfosuccinates or sulfosuccinamates. Examples of sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, alcohols, ethoxylated alcohols or of fatty acid esters. Examples of phosphates are phosphate esters. Examples of carboxylates are alkyl carboxylates and carboxylated alcohols or ethoxylated alkylphenols.

[00174] Suitable non-ionic surfactants are alkoxylates, N-substituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants and mixtures thereof. Examples of alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids, or fatty acid esters that have been alkoxylated with 1 to 50 equivalents. Ethylene oxide and/or propylene oxide can be used for alkoxylation, preferably ethylene oxide. Examples of N-substituted fatty acid amides are fatty acid glucamides or fatty acid alkanolamides. Examples of esters are fatty acid esters, glycerol esters or monoglycerides. Examples of sugar-based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or alkylpolyglucosides. Examples of polymeric surfactants are homo- or copolymers of vinyl pyrrolidone, vinyl alcohols or vinyl acetate.

[00175] Suitable cationic surfactants are quaternary surfactants, for example, quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines. Suitable amphoteric surfactants are alkyl betaines and imidazolines. Suitable block polymers are block polymers of type A-B or A-B-A comprising blocks of polyethylene oxide and polypropylene oxide, or of type A-B-C comprising alkanol, polyethylene oxide and polypropylene oxide. Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkaline salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinyl amines or polyethylene amines.

[00176] Suitable adjuvants are compounds that have negligible or no pesticidal activity, and that improve the biological performance of compound I on the target. Examples are surfactants, mineral or vegetable oils and other auxiliaries. Additional examples are listed by Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.

[00177] Suitable thickeners are polysaccharides (for example, xanthan gum, carboxymethylcellulose), inorganic clays (organically modified or unmodified), polycarboxylates and silicates.

[00178] Suitable bactericides are bronopol and isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazolinones.

[00179] Suitable antifreeze agents are ethylene glycol, propylene glycol, urea and glycerin.

[00180] Suitable antifoam agents are silicones, long-chain alcohols and fatty acid salts.

[00181] Suitable dyes (for example, red, blue or green) are low water solubility pigments and water soluble dyes. Examples are inorganic colorants (e.g., iron oxide, titanium oxide, iron hexacyanoferrate) and organic colorants (e.g., alizarin-, azo-, and phthalocyanine colorants).

[00182] Suitable stickiness enhancers or binders are polyvinyl pyrrolidones, polyvinyl acetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes and cellulose ethers.

[00183] Examples of types of compositions and their preparations are:

i) Water-soluble concentrates (SL, LS)

[00184] 10 to 60% by weight of a compound I and 5 to 15% by weight of wetting agent (e.g., alkoxylated alcohols) are dissolved in water and/or in a water-soluble solvent (e.g., alcohols) ad 100%, by weight. The active substance dissolves when diluted with water.

ii) Dispersible concentrates (DC)

[00185] 5 to 25% by weight of a compound I and 1 to 10% by weight of dispersant (for example, polyvinyl pyrrolidone) are dissolved in organic solvent (for example, cyclohexanone) to 100% by weight . Dilution with water results in a dispersion.

iii) Emulsifiable concentrates (EC)

[00186] 15 to 70% by weight of a compound I and 5 to 10% by weight of emulsifiers (e.g. calcium dodecylbenzenesulfonate and ethoxylated castor oil) are dissolved in water-insoluble organic solvent (e.g. , aromatic hydrocarbon) ad 100%, by weight. Dilution with water results in an emulsion.

iv) Emulsions (EW, EO, ES)

[00187] 5 to 40% by weight of a compound I and 1 to 10% by weight of emulsifiers (for example, calcium dodecylbenzenesulfonate and ethoxylated castor oil) are dissolved in water-insoluble organic solvent 20 to 40 % by weight (e.g. aromatic hydrocarbon). This mixture is introduced into water ad 100%, by weight, through an emulsifying machine and produced into a homogeneous emulsion. Dilution with water results in an emulsion.

v) Suspensions (SC, OD, FS)

[00188] In an agitated ball mill, 20 to 60% by weight of a compound I are crushed with the addition of 2 to 10% by weight of dispersants and wetting agents (for example, sodium lignosulfonate and ethoxylated alcohol ), 0.1 to 2% by weight of thickener (e.g. xanthan gum) and water ad 100% by weight to result in a fine active substance suspension. Dilution with water results in a stable suspension of the active substance. For type FS composition, up to 40% by weight of binder (for example, polyvinyl alcohol) is added.

vi) Water dispersible granules and water soluble granules (WG, SG)

[00189] 50 to 80%, by weight, of a compound I are finely crushed with the addition of dispersants and wetting agents (for example, lignosulfonate and ethoxylated alcohol) to 100%, by weight, and prepared as water-dispersible or soluble granules in water by means of technical devices (e.g. extrusion, sprinkler tower, fluidized bed). Dilution with water results in a stable dispersion or solution of the active substance.

vii) Water dispersible powders and water soluble powders (WP, SP, WS)

[00190] 50 to 80%, by weight, of a compound I are ground in a grinder with a stator rotor with the addition of 1 to 5%, by weight, of dispersants (for example, sodium lignosulfonate), 1 to 3%, by weight, of wetting agents (e.g., ethoxylated alcohol) and solid carrier (e.g., silica gel) at 100%, by weight. Dilution with water results in a stable dispersion or solution of the active substance.

viii) Gel (GW, GF)

[00191] In an agitated ball mill, 5 to 25% by weight of a compound I are crushed with the addition of 3 to 10% by weight of dispersants (for example, sodium lignosulfonate), 1 to 5% , by weight, of thickener (e.g., carboxymethyl cellulose) and water ad 100%, by weight, to result in a fine suspension of the fine active substance. Dilution with water results in a stable suspension of the active substance.

ix) Microemulsion (ME)

[00192] 5 to 20%, by weight, of a compound I are added to 5 to 30%, by weight, of organic solvent blend (for example, fatty acid dimethyl amide and cyclohexanone), 10 to 25%, in weight, of a surfactant blend (for example, ethoxylated alcohol and ethoxylated arylphenol) and 100% water. The mixture is stirred for 1 h to spontaneously produce a thermodynamically stable microemulsion.

x) Microcapsules (CS)

[00193] An oily phase comprising 5 to 50%, by weight, of a compound I, 0 to 40%, by weight, of water-insoluble organic solvent (for example, aromatic hydrocarbon), 2 to 15%, by weight , of acrylic monomers (e.g., methylmethacrylate, methacrylic acid and di- or triacrylate) are dispersed in an aqueous solution of a protective colloid (e.g., polyvinyl alcohol). Radical polymerization results in the formation of poly(meth)acrylate microcapsules. Alternatively, an oily phase comprising 5 to 50% by weight of a compound I according to the invention, 0 to 40% by weight of water-insoluble organic solvent (e.g. aromatic hydrocarbon), and a monomer isocyanate (e.g. diphenylmethane-4,4'-diisocyanate) are dispersed in an aqueous solution of a protective colloid (e.g. polyvinyl alcohol). The addition of a polyamine (e.g. hexamethylenediamine) results in the formation of polyurea microcapsules. The amount of monomers to 1 to 10% by weight. The percentage, by weight, related to the total CS composition.

xi) Dustable powders (DP, DS)

[00194] 1 to 10%, by weight, of a compound I are finely crushed and mixed intimately with solid carrier (for example, finely divided kaolin) to 100%, by weight.

xii) Granules (GR, FG)

[00195] 0.5 to 30%, by weight, of a compound I are finely crushed and associated with a solid carrier (for example, silicate) at 100%, by weight. Granulation is obtained by extrusion, spray drying or fluidized bed.

xiii) Ultra-low volume (UL) liquids

[00196] 1 to 50%, by weight, of a compound I are dissolved in organic solvent (for example, aromatic hydrocarbon) at 100%, by weight.

[00197] Compositions type i) to xiii) may optionally comprise additional auxiliaries, such as 0.1 to 1% by weight of bactericides, 5 to 15% by weight of antifreeze agents, and 0.1 to 1% , by weight, of colorants.

[00198] Agrochemical compositions generally comprise between 0.01 and 95%, preferably between 0.1 and 90%, more preferably between 1 and 70%, and in particular between 10 and 60%, by weight, of the active substance. The active substances are used in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum).

[00199] For the purposes of treating plant propagation materials, particularly seeds, seed treatment solutions (LS), suspoemulsions (SE), fluid concentrates (FS), dry treatment powders (DS), water dispersible powders for slurry treatment (WS), water-soluble powders (SS), emulsions (ES), emulsifiable concentrates (EC) and gels (GF) are generally employed. The compositions in question provide, after two to ten times dilution, active substance concentrations of 0.01 to 60% by weight, preferably 0.1 to 40%, in ready-to-use preparations. Application can be carried out before or during sowing. Methods for applying compound I and compositions thereof, respectively, to plant propagation material, especially seeds, include covering, coating, pelletizing, dusting and dipping, as well as in-furrow application methods. Preferably, the compound I or compositions thereof, respectively, are applied to the plant propagation material by a method so that germination is not induced, for example, by seed covering, pelleting, coating and dusting.

[00200] When used in plant protection, the quantities of active substances applied are, depending on the type of effect desired, between 0.001 to 2 kg per ha, preferably 0.005 to 2 kg per ha, more preferably 0.05 to 0 .9 kg per ha and, in particular, from 0.1 to 0.75 kg per ha.

[00201] When treating plant propagation materials such as seeds, for example, by dusting, coating or soaking the seed, amounts of active substance from 0.1 to 1000 g, preferably from 1 to 1000 g, more preferably from 1 to 100 g, and most preferably 5 to 100 g per 100 kg of plant propagation material (preferably seeds) are generally required.

[00202] When used to protect stored materials or products, the amount of active substance applied depends on the type of application area and the desired effect. Quantities usually applied to protect materials are 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of active substance per cubic meter of treated material.

[00203] Various types of oils, wetting agents, adjuvants, fertilizers or micronutrients and even pesticides (for example, herbicides, insecticides, fungicides, growth regulators, protectants, biopesticides) can be added to the active substances or compositions comprising them. as premix or, if appropriate, not until immediately before use (tank mix). These agents can be mixed with the compositions according to the invention in a weight ratio of 1:100 to 100:1, preferably 1:10 to 10:1.

[00204] A pesticide is generally a chemical or biological agent (such as active pest ingredient, compound, composition, virus, bacteria, antimicrobial or disinfectant) that, through its effect, prevents, incapacitates, kills or otherwise discourages pests. Target pests may include insects, plant pathogens, weeds, shellfish, birds, mammals, fish, nematodes (roundworms), and microbes that destroy property, cause nuisance, spread disease, or are disease vectors. The term “pesticide” also includes growth regulators that alter the expected growth, flowering, or reproduction rate of plants; defoliants that cause leaves or other foliage to fall from a plant, usually to facilitate harvesting; desiccants that promote the drying of living tissue, such as undesirable upper parts of plants; plant activators that activate plant physiology to defend against certain pests; phytoprotectors that reduce the unwanted herbicidal action of pesticides on crop plants; and plant growth promoters that affect plant physiology, for example, to increase plant growth, biomass, yield or any other quality parameter of harvestable goods from plant crops.

[00205] The user applies the composition according to the invention, generally from a pre-dosing device, a backpack sprayer, a spray tank, a spray plane or an irrigation system. Generally, the agrochemical composition is produced with water, buffer and/or additional auxiliaries until the desired application concentration or the ready-to-use spray liquid or the agrochemical composition according to the invention is thus obtained. Generally, 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquid are applied per hectare of usable agricultural area.

[00206] According to one embodiment, individual components of the composition according to the invention, such as parts of a kit or parts of a binary or ternary mixture, can be mixed by the user himself in a spray tank or any other type of container used for applications (e.g. seed treatment drums, seed pelleting machinery, backpack sprayer) and other auxiliaries can be added if appropriate.

[00207] Accordingly, an embodiment of the invention is a kit for preparing a useful pesticide composition, the kit comprising a) a composition comprising component 1) as defined in the present application and at least one auxiliary; and b) a composition comprising component 2) as defined in the present application and at least one auxiliary and; optionally c) a composition comprising at least one auxiliary and optionally an additional new active component 3) as defined in the present application.

[00208] Mixing compounds I or compositions comprising them in the form of use as fungicides, with other fungicides, in many cases, results in an expansion of the spectrum of fungicidal activity to be obtained or in the prevention of the development of resistance to fungicides . Furthermore, in many cases, synergistic effects are obtained.

[00209] The following list of pesticides II (e.g., active pesticide substances and biopesticides), together with compounds I that can be used, is intended to illustrate the possible combinations, but not be limited to them: A) Inhibitors of respiration - Complex III inhibitors at the Qo site: azoxystrobin (A.1.1), coumethoxystrobin (A.1.2), coumoxystrobin (A.1.3), dimoxystrobin (A.1.4), enestroburin (A.1.5), phenaminstrobin (A.1.6 ), phenoxystrobin/fluphenoxystrobin (A.1.7), fluoxastrobin (A.1.8), kresoxim-methyl (A.1.9), mandestrobin (A.1.10), metominostrobin (A.1.11), orisastrobin (A.1.12), picoxystrobin ( A.1.13), pyraclostrobin (A.1.14), pyramethostrobin (A.1.15), pyraoxystrobin (A.1.16), trifloxystrobin (A.1.17), 2-(2-(3-(2,6-dichlorophenyl)-1 -methyl-allylideneaminooxymethyl)-phenyl)-2-methoxyimino-N-methyl-acetamide (A.1.18), piribencarb (A.1.19), triclopiricarb/chlorodincarb (A.1.20), famoxadone (A.1.21), fenamidone (A .1.21a), methyl-N-[2-[(1,4-dimethyl-5-phenyl-pyrazol-3-yl)oxylmethyl]phenyl]-N-methoxy-carbeamate (A.1.22), methyltetrapole (A. 1.25), (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]-oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide (A.1.34) , (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide (A.1.35), pyriminostrobin (A. 1.36), bifujunzi (A.1.37), 2-(ortho-((2,5-dimethylphenyl-oxymethylen)phenyl)-3-methoxy-acrylic acid methyl ester (A.1.38); - complex III inhibitors at the Qi site: cyazofamide (A.2.1), amisulbrom (A.2.2), [(6S,7R,8R)-8-benzyl-3-[(3-hydroxy-4-methoxy-pyridine- 2-carbeonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl] 2-methylpropanoate (A.2.3), fenpicoxamide (A.2.4), florylpicoxamide (A.2.5); - complex II inhibitors: benodanil (A.3.1), benzovindiflupyr (A.3.2), bixafem (A.3.3), boscalid (A.3.4), carboxine (A.3.5), fenfuram (A.3.6), fluopyram ( A.3.7), flutolanil (A.3.8), fluxapyroxad (A.3.9), furametpyr (A.3.10), isofetamide (A.3.11), isopyrazam (A.3.12), mepronil (A.3.13), oxycarboxin (A .3.14), penflufen (A.3.15), penthiopyrad (A.3.16), pidiflumetofen (A.3.17), pyraziflumide (A.3.18), sedaxane (A.3.19), tecloftalam (A.3.20), thifluzamide (A. 3.21); 5-fluoro-1-methyl-pyrazola-4-carboxamide (A.3.29), methyl (E)-2-[2-[(5-cyano-2-methyl-phenoxy)methyl]phenyl]-3-methoxy- prop-2-enoate (A.3.30), isoflucipram (A.3.31), 2-(difluoromethyl)-N-(1,1,3-trimethyl-indan-4-yl)pyridine-3-carboxamide (A.3.32 ), 2-(difluoromethyl)-N-[(3R)- 1,1,3-trimethylindan-4-yl]pyridine-3-carboxamide (A.3.33), 2-(difluoromethyl)-N-(3-ethyl -1,1-dimethyl-indan-4-yl)pyridine-3-carboxamide (A.3.34), 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethyl-indan-4 -yl]pyridine-3-carboxamide (A.3.35), 2-(difluoromethyl)-N-(1,1-dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide (A.3.36), 2-(difluoromethyl)-N-[(3R)-1,1-dimethyl-3-propyl-indan-4-yl]pyridine-3-carboxamide (A.3.37), 2-(difluoromethyl)-N-(3 -isobutyl-1,1-dimethyl-indan-4-yl)pyridine-3-carboxamide (A.3.38), 2-(difluoromethyl)-N-[(3R)-3-isobutyl-1,1-dimethyl-indan -4-yl]pyridine-3-carboxamide (A.3.39); - other respiratory inhibitors: diflumetorim (A.4.1); nitrophenyl derivatives: binapacryl (A.4.2), dinobutone (A.4.3), dinocape (A.4.4), fluazinam (A.4.5), meptildinocape (A.4.6), ferinzone (A.4.7); organometallic compounds: fentin salts, for example, fentin acetate (A.4.8), fentin chloride (A.4.9) or fentin hydroxide (A.4.10); ametoctradine (A.4.11); siltiofam (A.4.12); B) Sterol biosynthesis inhibitors (SBI fungicides) - C14 demethylase inhibitors: triazoles: azaconazole (B.1.1), bitertanol (B.1.2), bromuconazole (B.1.3), cyproconazole (B.1.4), difenoconazole (B .1.5), diniconazole (B.1.6), diniconazole-M (B.1.7), epoxiconazole (B.1.8), fenbuconazole (B.1.9), fluquinconazole (B.1.10), flusilazole (B.1.11), flutriafol ( B.1.12), hexaconazole (B.1.13), imibenconazole (B.1.14), ipconazole (B.1.15), metconazole (B.1.17), myclobutanil (B.1.18), oxpoconazole (B.1.19), paclobutrazole (B .1.20), penconazole (B.1.21), propiconazole (B.1.22), prothioconazole (B.1.23), simeconazole (B.1.24), tebuconazole (B.1.25), tetraconazole (B.1.26), triadimefon (B. 1.27), triadimenol (B.1.28), triticonazole (B.1.29), uniconazole (B.1.30), 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)- 1- [5-[4-(2,2,2-trifluoroethoxy)phenyl]-2-pyridyl]propan-2-ol (B.1.31), 2-(2,4-difluorophenyl)- 1,1-difluoro -3-(tetrazol-1-yl)-1-[5-[4-(trifluoromethoxy)phenyl]-2-pyridyl]propan-2-ol (B.1.32), ipfentrifluconazole (B.1.37), mefentrifluconazole (B .1.38), 2-(chloromethyl)-2-methyl-5-(p-tolylmethyl)-1-(1,2,4-triazol-1-ylmethyl)cyclopentanol (B.1.(43) imidazoles: imazalil ( B.1.44), pefurazoate (B.1.45), prochloraz (B.1.46), triflumizole (B.1.47); pyrimidines, pyridines, piperazines: fenarimol (B.1.49), pyrifenox (B.1.50), triporine (B.1.51), [3-(4-chloro-2-fluoro-phenyl)-5-(2,4-difluorophenyl )isoxazol-4-yl]-(3-pyridyl)methanol (B.1.52); - Delta14 reductase inhibitors: aldimorph (B.2.1), dodemorph (B.2.(2) dodemorph acetate (B.2.3), fenpropimorph (B.2.4), tridemorph (B.2.5), fenpropidim (B.2.6 ), piperalim (B.2.7), spiroxamine (B.2.8); - 3-keto reductase inhibitors: fenexamide (B.3.1); - other sterol biosynthesis inhibitors: chlorfenomizole (B.4.1); nucleic acid synthesis - fungicides phenylamides or acyl amino acids: benalaxyl (C.1.1), benalaxyl-M (C.1.2), chiralaxyl (C.1.3), metalaxyl (C.1.4), metalaxyl-M (C.1.5), ofurace (C.1.6), oxadixyl (C.1.7); - other nucleic acid synthesis inhibitors: himexazole (C.2.1), octylinone (C.2.2), oxolinic acid (C.2.3), bupyrimate (C.2.4), 5-fluorocytosine (C.2.5), 5-fluoro -2-(p-tolylmethoxy)pyrimidin-4-amine (C.2.6), 5-fluoro- 2-(4-fluorophenylmethoxy)pyrimidin-4-amine (C.2.7), chlorophenylmethoxy)pyrimidin-4 amine (C. 2.8); D) Cell division and cytoskeleton inhibitors - tubulin inhibitors: benomyl (D.1.1), carbendazim (D.1.2), fuberidazole (D1.3), thiabendazole (D.1.4), thiophanate-methyl (D.1.5), pyridaclomethyl (D.1.6), N-ethyl-2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]butanamide (D.1.8), N-ethyl-2-[(3-ethynyl-8- methyl-6-quinolyl)oxy]-2-methylsulfanyl-acetamide (D.1.9), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-(2-fluoroethyl)butanamide (D. 1.10), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-(2-fluoroethyl)-2-methoxy-acetamide (D.1.11), 2-[(3-ethynyl-8 - methyl-6-quinolyl)oxy]-N-propyl-butanamide (D.1.12), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2-methoxy-N-propyl-acetamide ( D.1.13), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2-methylsulfanyl-N-propyl-acetamide (D.1.14), 2-[(3-ethynyl-8-methyl -6-quinolyl)oxy]-N-(2-fluoroethyl)-2-methylsulfanyl-acetamide (D.1.15), 4-(2-bromo-4-fluoro-phenyl)-N-(2-chloro-6- fluoro-phenyl)-2,5-dimethyl-pyrazol-3-amine (D.1.16); - other cell division inhibitors: diethofencarb (D.2.1), etaboxam (D.2.2), pencycuron (D.2.3), fluopicolide (D.2.4), zoxamide (D.2.5), metrafenone (D.2.6), pyriofenone (D.2.7); E) Amino acid and protein synthesis inhibitors - methionine synthesis inhibitors: cyprodinil (E.1.1), mepanipyrim (E.1.2), pyrimethanil (E.1.3); - protein synthesis inhibitors: blasticidin-S (E.2.1), kasugamycin (E.2.2), kasugamycin hydrochloride hydrate (E.2.3), mildiomycin (E.2.4), streptomycin (E.2.5), oxytetracycline ( E.2.6); F) Signal transduction inhibitors - MAP/histidine kinase inhibitors: fluoroimide (F.1.1), iprodione (F.1.2), procymidone (F.1.3), vinclozolin (F.1.4), fludioxonil (F.1.5); - G protein inhibitors: quinoxifene (F.2.1); G) Lipid and membrane synthesis inhibitors - Phospholipid biosynthesis inhibitors: edifenfos (G.1.1), iprobenfos (G.1.2), pyrazophos (G.1.3), isoprothiolane (G.1.4); - lipid peroxidation: dichloran (G.2.1), quintazene (G.2.2), technazene (G.2.3), tolclofos-methyl (G.2.4), biphenyl (G.2.5), cloronab (G.2.6), etridiazole (G.2.7); - phospholipid biosynthesis and cell wall deposition: dimethomorph (G.3.1), flumorph (G.3.2), mandipropamide (G.3.3), pyrimorph (G.3.4), bentiavalicarb (G.3.5), iprovalicarb (G.3.6 ), valifenalate (G.3.7); - compounds that affect cell membrane permeability and fatty acids: propamocarb (G.4.1); - oxysterol binding protein inhibitors: oxathiapiproline (G.5.1), fluoxapiproline (G.5.3), 4-[1-[2-[3-(difluoromethyl)-5-methyl-pyrazol-1-yl]acetyl] -4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide (G.5.4), 4-[1-[2-[3,5-bis(difluoromethyl)pyrazol-1-yl]acetyl] -4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide (G.5.5), 4-[1-[2-[3-(difluoromethyl)-5-(trifluoromethyl)pyrazol-1-yl ]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide (G.5.6), 4-[1-[2-[5-cyclopropyl-3-(difluoromethyl)pyrazol-1- yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide (G.5.7), 4-[1-[2-[5-methyl-3-(trifluoromethyl)pyrazol-1 -yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide (G.5.8), 4-[1-[2-[5-(difluoromethyl)-3-(trifluoromethyl) pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide (G.5.9), 4-[1-[2-[3,5-bis(trifluoromethyl) pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide (G.5.10), (4-[1-[2-[5-cyclopropyl-3-( trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide (G.5.11); H) Inhibitors with Multi-Site Action - inorganic active substances: Bordeaux mixture (H.1.1), copper (H.1.2), copper acetate (H.1.3), copper hydroxide (H.1.4), copper oxychloride (H.1.5), basic copper sulfate (H.1.6), sulfur (H.1.7); - thiocarbamates and dithiocarbamates: ferbam (H.2.1), mancozeb (H.2.2), maneb (H.2.3), metham (H.2.4), metiram (H.2.5), propineb (H.2.6), thiram (H .2.7), zinab (H.2.8), ziram (H.2.9); - organochlorin compounds: anilazine (H.3.1), chlorothalonil (H.3.2), Captafol (H.3.3), Captan (H.3.4), folpet (H.3.5), diclofluanide (H.3.6), dichlorophene (H. 3.7), hexachlorobenzene (H.3.8), pentachlorphenol (H.3.9) and its salts, phthalide (H.3.10), tolylfluanide (H.3.11); - guanidines and others: guanidine (H.4.1), dodine (H.4.2), free base dodine (H.4.3), guazatine (H.4.4), guazatine acetate (H.4.5), iminoctadine (H.4.6 ), iminoctadine triacetate (H.4.7), iminoctadine-tris(albesylate) (H.4.8), dithianone (H.4.9), 2,6-dimethyl-1H,5H-[1,4]dithyino[2,3 -c:5,6- c']dipyrrole-1,3,5,7(2H,6H)-tetraone (H.4.10); I) Cell wall synthesis inhibitors - glucan synthesis inhibitors: validamycin (I.1.1), polyoxin B (I.1.2); - melanin synthesis inhibitors: pyroquilone (I.2.1), tricyclazole (I.2.2), carpropamide (I.2.3), dicyclomet (I.2.4), fenoxanil (I.2.5); J) Plant defense inducers - acibenzolar-S-methyl (J.1.1), probenazole (J.1.2), isotianil (J.1.3), thiadinil (J.1.4), calcium prohexadione (J.1.5); phosphonates: fosetyl (J.1.6), fosetyl aluminum (J.1.7), phosphoric acid and its salts (J.1.8), calcium phosphonate (J.1.11), potassium phosphonate (J.1.12), potassium bicarbonate or sodium (J.1.9), 4-cyclopropyl-N-(2,4-dimethoxyphenyl)thiadiazole-5-carboxamide (J.1.10); K) Unknown mode of action - bronopol (K.1.1), quinomethionate (K.1.2), cyflufenamide (K.1.3), cymoxanil (K.1.4), dazomet (K.1.5), debacarb (K.1.6), diclocimet (K.1.7), diclomezine (K.1.8), diphenzoquat (K.1.9), diphenzoquat methylsulfate (K.1.10), diphenylamine (K.1.11), phenitropane (K.1.12), fenpyrazamine (K.1.13), flumetover (K.1.14), flusulfamide (K.1.15), flutianil (K.1.16), harpina (K.1.17), metasulfocarb (K.1.18), nitrapyrin (K.1.19), nitrothal-isopropyl (K.1.20) , tolprocarb (K.1.21), oxin-copper (K.1.22), proquinazide (K.1.23), tebufloquine (K.1.24), teclophthalam (K.1.25), triazoxide (K.1.26), N'-(4 -(4-chloro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methyl formamidine (K.1.27), N'-(4-(4-fluoro-3-trifluoromethyl -phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methyl formamidine (K.1.28), N'-[4- [[3-[(4-chlorophenyl)methyl]-1,2, 4-thiadiazol-5-yl]oxy]-2,5-yl-dimethyl-phenyl]-N-ethyl-N-methyl-formamidine (K.1.29), N'-(5-bromo-6-indan-2 -yloxy-2-methyl-3-pyridyl)-N-ethyl-N-methyl-formamidine (K.1.30), N'-[5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]- 2-methyl-3-pyridyl]-N-ethyl-N-methyl-formamidine (K.1.31), N'-[5-bromo-6-(4-isopropylcyclohexoxy)-2-methyl-3-pyridyl]-N -ethyl-N-methyl-formamidine (K.1.32), N'-[5-bromo-2-methyl-6-(1-phenylethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine (K .1.33), N'-(2-methyl-5-trifluoromethyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl-N-methyl formamidine (K.1.34), N'-(5-difluoromethyl -2-methyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl-N-methyl formamidine (K.1.35), 2-(4-chloro-phenyl)-N-[4-(3, 4-dimethoxy-phenyl)-isoxazol-5-yl]-2-prope-2-ynyloxy-acetamide (K.1.36), 3-[5-(4-chloro-phenyl)-2,3-dimethyl-isoxazolidin- 3-yl]-pyridine (pyrisoxazole) (K.1.37), 3-[5-(4-methylphenyl)-2,3-dimethyl-isoxazolidin-3yl]-pyridine (K.1.38), 5-chloro-1 -(4,6-dimethoxy-pyrimidin-2-yl)-2-methyl- 1H-benzoimidazole (K.1.39), ethyl (Z)-3-amino-2-cyano-3-phenyl-prope-2-enoate (K.1.40), picarbutrazox (K.1.41), pentyl N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate (K.1.42), but-3-ynyl N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate (K. 1.43), ipflufenoquine (K.1.44), quinofumelin (K.1.47), 2-(6-benzyl-2-pyridyl)quinazoline (K.1.50), 2-[6-(3-fluoro-4-methoxy-phenyl )-5-methyl-2-pyridyl]quinazoline (K.1.51), diclobentiazox (K.1.52), N'-(2,5-dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine (K.1.53), pyriphenamine (K.1.54); M) Growth regulators - abscisic acid (M.1.1), amidochlor, ancymidola, 6- benzylaminopurine, brassinolide, butralin, chlormequat, chlormequat chloride, choline chloride, cyclanilide, daminozide, diquegulac, dimethipine, 2,6- dimethylpuridine, ethephone, flumetralin, flurprimidol, flutiacet, forchlorfenurone, gibberellic acid, inabenfide, indole-3-acetic acid, maleic hydrazide, mefluidide, mepiquat, mepiquat chloride, naphthaleneacetic acid, N-6- benzyladenine, paclobutrazol, prohexadione, calcium prohexadione, prohydrojasmon, thidiazurone, triapentenol, tributyl phosphorotrithioate, 2,3,5-triiodobenzoic acid, trinexapaque-ethyl and uniconazole; N) Herbicides of classes N.1 to N.15 N.1 Lipid biosynthesis inhibitors: aloxidim, aloxidim-sodium, butroxydim, clethodim, clodinafop, clodinafop-propargyl, cycloxidim, cialofop, cialofop-butyl, diclofop, diclofop-methyl , fenoxaprop, fenoxaprope-ethyl, fenoxaprope-P, fenoxaprope-P-ethyl, fluazifop, fluazifop-butyl, fluazifop-P, fluazifop-P-butyl, haloxyfop, haloxyfop-methyl, haloxyfop-P, haloxyfop-P-methyl, metamifop , pinoxadem, profoxidim, propaquizafop, quizalofop, quizalofop-ethyl, quizalofop-tefuryl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, sethoxydim, tepraloxidim, tralkoxidim, 4-(4'-chloro-4-cyclopropyl -2'-fluoro[1,1'-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (1312337-72-6) ; 4-(2',4'-dichloro-4-cyclopropyl[1,1'-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H) -one (1312337-45-3); 4-(4'-chloro-4-ethyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3( 6H)-one (1033757-93-5); 4-(2',4'-dichloro-4-ethyl[1,1'-biphenyl]-3-yl)-2,2,6,6-tetramethyl-2H-pyran-3,5(4H,6H) -dione (1312340-84-3); 5-(acetyloxy)-4-(4'-chloro-4-cyclopropyl-2'-fluoro[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6, 6-tetramethyl-2H-pyran-3-one (1312337-48-6); 5-(acetyloxy)-4-(2',4'-dichloro-4-cyclopropyl-[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6 -tetramethyl-2H-pyran-3-one; 5-(acetyloxy)-4-(4'-chloro-4-ethyl-2'-fluoro[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6, 6-tetramethyl-2H-pyran-3-one (1312340-82-1); 5-(acetyloxy)-4-(2',4'-dichloro-4-ethyl[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6- tetramethyl-2H-pyran-3-one (1033760-55-2); 4-(4'-chloro-4-cyclopropyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5- oxo-2H-pyran-3-yl carbonic acid methyl ester (1312337-51-1); 4-(2',4'-dichloro-4-cyclopropyl-[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl acid methyl ester carbonic -5-oxo-2H-pyran-3-yl; 4-(4'-Chloro-4-ethyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6- acid methyl ester carbonic tetramethyl-5-oxo-2H-pyran-3-yl (1312340-83-2); 4-(2',4'-dichloro-4-ethyl[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-acid methyl ester 5-oxo-2H-pyran-3-yl carbonic acid (1033760-58-5); benfuresate, butylate, cycloate, dalapone, dimepiperate, EPTC, esprocarb, etofumesate, flupropanate, molinate, orbencarb, pebulate, prosulfocarb, TCA, thiobencarb, thiocarbozil, triallate, vernolate; N2 m , halosulfuron, halosulfuron-methyl, imazosulfuron, iodosulfuron, iodosulfuron-methyl-sodium, iofensulfuron, iofensulfuron-sodium, mesosulfuron, metazosulfuron, metsulfuron, metsulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron, primisulfuron, primisulfuron- methyl, urom, prosulfuron, pyrazosulfuron , pyrazosulfurom-ethyl, rimsulfurom, sulfometurom, sulfometurom-methyl, sulfosulfuron, thifensulfuron, thifensulfuron-methyl, triasulfurom, tribenurone, tribenuron-methyl, trifloxysulfuron, triflusulfuron, triflusulfuron-methyl, tritosulfuron, imazametabenz, imazametabenz-methyl, imazapic, , imazapyr , imazaquim, imazethapyr; cloransulam, cloransulam-methyl, diclosulam, flumetsulam, florasulam, metosulam, penoxsulam, pirimisulfam, piroxsulam; bispiribac, bispiribac-sodium, pyribenzoxim, pyrifthalide, piriminobac, piriminobac-methyl, pyritiobac, pyritiobac-sodium, 4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy] acid ester phenyl]methyl]amino]-benzoic acid (420138-41-6), propyl 4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]-benzoic acid ester ( 420138-40-5), N-(4-bromophenyl)-2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzenemethanamine (420138-01-8); flucarbozone, flucarbozone-sodium, propoxycarbozone, propoxycarbozone-sodium, thiencarbozone, thiencarbozone-methyl; triafamone; N.3 Photosynthesis inhibitors: amicarbozone; chlorotriazine; ametrim, atrazine, chloridazone, cyanazine, desmetrim, dimetmetrim, hexazinone, metribuzim, prometone, prometrim, propazine, simazine, simetrim, terbumetone, terbuthylazim, terbutrim, triethazim; Chlorobromurona, chlorotolurona, chloroxurona, dimefurone, diurone, fluometurona, isoproturona, isouroona, linurone, metamron, metabenziazurona, metobenzurona, metoxurona, monolinurona, neburone, sidurona, tebutiurona, thiadiazurona, dismeditifam, carbutum Late, phenmedifam, phenmedifam-ethyl, bromophenoxim, bromixinil and its salts and esters, ioxynil and its salts and esters, bromacil, lenacil, terbacil, bentazone, bentazomsodium, pyridate, pyridafol, pentanochlor, propanil; diquat, diquat dibromide, paraquat, paraquat dichloride, paraquat dimethylsulfate; N.4 Protoporfyrinogen inhibitors IX oxidase: acifluorrfem, acifluorfem-soothed, azafenidine, bencarbazone, benzphendizone, bifenox, buttaphenacil, carfentrazone-ethyl, chlormetoxifem, cynidom-phytyl, fluzolato, flufenry, flufian RAC, Flumiclorac-Pentlic , flumioxazin, fluoroglycophen, fluoroglycophen-ethyl, flutiacete, flutiacete-methyl, medosafem, halosafem, lactofem, oxadiargyl, oxadiazone, oxyfluorfen, pentoxazone, profluazole, pyraclonil, pyraflufen, pyraflufen-ethyl, saflufenacil, sulfentrazone, thidiazimine, trifludimoxaz, ina, ethyl [3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2- pyridyloxy]acetate (353292-31-6), N-ethyl-3-(2,6-dichloro-4-trifluoro-methylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (452098-92-9), N-tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazola-1-carboxamide (915396-43-9), N-ethyl-3-(2-chloro- 6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazola-1-carboxamide (452099-05-7), N-tetrahydrofurfuryl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)- 5-methyl-1H-pyrazola-1-carboxamide (452100-03-7), 3-[7-fluoro-3-oxo-4-(prope-2-ynyl)-3,4-dihydro-2H- benzo[1,4]oxazin-6-yl]-1,5-dimethyl-6-thioxo-[1,3,5]triazinan-2,4-dione (451484-50-7), 2-(2, 2,7-trifluoro-3-oxo-4-prope-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-4,5,6,7-tetra -hydro-isoindole-1,3-dione (1300118-96-0), 1-methyl-6-trifluoromethyl-3-(2,2,7-tri-fluoro-3-oxo-4-prope-2-ynyl -3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-1H-pyrimidine-2,4-dione (1304113-050), methyl (E)-4-[2-chloro -5-[4-chloro-5-(difluoromethoxy)-1H-methyl-pyrazol-3-yl]-4-fluoro-phenoxy]-3-methoxy-but-2-enoate (948893-00-3), 3 -[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)-1H-pyrimidine-2,4-dione (212754-02-4 ); N.5 Bleaching herbicides: beflubutamide, diflufenicam, fluridone, flurochloridone, flurtamon, norflurazone, picolinafem, 4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)pyrimidine (180608-33-7); benzobicyclone, benzofenape, biciclopyrone, clomazone, fenquintrione, isoxaflutole, mesotrione, pyrasulfotole, pyrazolinate, pyrazoxifen, sulcotrione, tefuryltrione, tembotrione, tolpiralate, topramezone; aclonifem, amitrola, flumeturom; N.6 EPSP synthase inhibitors: glyphosate, glyphosate-isopropylammonium, glyposate-potassium, glyphosate-trimesium (sulfosate); N.7 Glutamine synthase inhibitors: bilanafos (bialafos), bilanafos-sodium, glufosinate, glufosinate-P, glufosinate-ammonium; N.8 DHP synthase inhibitors: asulam; N.9 Mitosis inhibitors: benfluralin, butralin, dinitramine, ethalfluralin, fluchloralin, oryzalin, pendimethalin, prodiamine, trifluralin; amiprophos, amiprophos-methyl, butamiphos; chlorthal, chlorthal-dimethyl, dithiopyr, thiazopyr, propyzamide, tebutam; carbetamide, chlorpropam, flamprope, flamprope-isopropyl, flamprope-methyl, flamprope-M-isopropyl, flamprope-M-methyl, profam; N.10 VLCFA inhibitors: acetochlor, alachlor, butachlor, dimethachlor, dimethenamid, dimethenamid-P, metazachlor, metolachlor, metolachlor-S, petoxamide, pretilachlor, propachlor, propisochlor, tenylchlor, flufenacet, mefenacet, diphenamide, naproanilide, napropamide, napropamide -M, fentrazamide, anilophos, cafenstrola, fenoxasulfone, ipfencarbozone, piperophos, pyroxasulfone, isoxazoline compounds of formulas II.1, II.2, II.3, II.4, II.5, II.6, II.7, II .8 and II.9 N.11 Cellulose biosynthesis inhibitors: chlorthiamide, diclobenil, flupoxam, indaziflam, isoxaben, triaziflam, 1-cyclohexyl-5-pentafluorophenyloxy-14-[1,2,4,6]thiatriazin-3-ylamine (175899-01- 1); N.12 Uncoupling herbicides: dinoseb, dinoterb, DNOC and their salts; N.13 Auxin herbicides: 2,4-D and its salts and esters, clacifos, 2,4-DB and its salts and esters, aminocyclopoirachlor and its salts and esters, aminopyralid and its salts such as aminopyralid-dimethylammonium, aminopyralid-tris( 2-hydroxypropyl)ammonium and its esters, benazoline, ethyl benazoline, chloraben and its salts and esters, clomeprop, clopyralid and its salts and esters, dicamba and its salts and esters, dichlorprop and its salts and esters, dichlorprope-P and its salts and esters, fluroxypyr, fluroxypyr-butomethyl, fluroxypyr-methyl, halauxifen and their salts and esters (943832-60-8); and its salts and esters, MCPA-thioethyl, MCPB and its salts and esters, mecoprop and its salts and esters, mecoprop-P and its salts and esters, picloram and its salts and esters, quinclorac, quinmerac, TBA (2,3, 6) and its salts and esters and triclopyr and its salts and esters, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylic acid, benzyl 4 -amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylate (139066172-9); N.14 Auxin transport inhibitors: diflufenzopyr, diflufenzopyr-sodium, naptalam, naptalam-sodium; N.15 Other herbicides: bromobutide, chlorflurenol, methyl chlorflurenol, cinmethylline, cumilurone, cyclopyrimorate (499223-49-3) and its salts and esters, dalapone, dazomet, diphenzoquat, diphenzoquat methylsulfate, dimethipine, DSMA, dinrom, endotal and its salts, etobenzanide, flurenol, flurenol-butyl, flurprimidol, fosamine, fosamine-ammonium, indanophane, maleic hydrazide, mefluidide, metam, methiozoline (403640-27-7), methyl azide, methyl bromide, methyl-dynrone, iodide methyl, MSMA, oleic acid, oxaziclomephone, pelargonic acid, pyributicarb, quinoclamine, tridiphane; O) Insecticides of classes O.1 to O.29 O.1 Acetylcholine esterase (AChE) inhibitors: aldicarb (O.1.1), alanicarb (O.1.2), bendiocarb (O.1.3), benfuracarb (O.1.4) , butocarboxim (O.1.5), butoxycarboxim (O.1.6), carbaryl (O.1.7), carbofuran (O.1.8), carbosulfan (O.1.9), ethiofencarb (O.1.10), fenobucarb (O.1.11), formetanate (O.1.12), furatiocarb (O.1.13), isoprocarb (O.1.14), methiocarb (O.1.15), methomyl (O.1.16), metolcarb (O.1.17), oxamyl (O.1.18), pirimicarb (O.1.19), propoxur (O.1.20), thiodicarb (O.1.21), thiophanox (O.1.22), trimetacarb (O.1.23), XMC (O.1.24), xylylcarb (O.1.25), triazamate ( O.1.26), acephate (O.1.27), azamethiphos (O.1.28), azinphosethyl (O.1.29), azinphosmethyl (O.1.30), cadusaphos (O.1.31), chlorethoxyphos (O.1.32), chlorfenvinphos (O.1.33), chlormephos (O.1.34), chlorpyrifos (O.1.35), chlorpyrifos-methyl (O.1.36), coumaphos (O.1.37), cyanophos (O.1.38), demetom-S-methyl (O .1.39), diazinom (O.1.40), dichlorvos/ DDVP (O.1.41), dicrotophos (O.1.42), dimethoate (O.1.43), dimethylvinphos (O.1.44), disulfotom (O.1.45), EPN ( O.1.46), ethion (O.1.47), ethoprophos (O.1.48), famfur (O.1.49), fenamiphos (O.1.50), fenitrothion (O.1.51), fenthion (O.1.52), fosthiazate (O .1.53), heptenophos (O.1.54), imiciaphos (O.1.55), isofenphos (O.1.56), isopropyl O- (methoxyaminothio-phosphoryl) salicylate (O.1.57), isoxathione (O.1.58), malathion (O .1.59), mecarbon (O.1.60), methamidophos (O.1.61), methidathion (O.1.62), mevinphos (O.1.63), monocrotophos (O.1.64), naled (O.1.65), omethoate (O. 1.66), oxidemethyl-methyl (O.1.67), parathion (O.1.68), parathion-methyl (O.1.69), phentoate (O.1.70), phorate (O.1.71), phosalone (O.1.72), phosmet (O.1.73), phosfamidon (O.1.74), phoxim (O.1.75), pirimiphos-methyl (O.1.76), profenofos (O.1.77), propetamphos (O.1.78), prothiophos (O.1.79), pyraclophos (O.1.80), pyridafenthion (O.1.81), quinalphos (O.1.82), sulfotepe (O.1.83), tebupirimphos (O.1.84), temephos (O.1.85), terbufos (O.1.86), tetrachlorvinphos (O.1.87), thiometom (O.1.88), triazophos (O.1.89), trichlorfon (O.1.90), vamidothion (O.1.91); O.2 GABA-dependent chloride channel antagonists: endosulfan (O.2.1), chlordane (O.2.2), etiprole (O.2.3), fipronil (O.2.4), flufiprola (O.2.5), pyrafluprole (O .2.6), pyriprola (O.2.7); O.3 Sodium channel modulators: acrinathrin (O.3.1), allethrin (O.3.2), d-cis-trans allethrin (O.3.3), d-trans allethrin (O.3.4), bifenthrin (O.3.5 ), kappa-bifenthrin (O.3.6), bioalethrin (O.3.7), bioalethrin S-cyclopentenyl (O.3.8), bioresmethrin (O.3.9), cycloprothrin (O.3.10), cyfluthrin (O.3.11), beta -cyfluthrin (O.3.12), cyhalothrin (O.3.13), lambda-cyhalothrin (O.3.14), gamma-cyhalothrin (O.3.15), cypermethrin (O.3.16), alpha-cypermethrin (O.3.17), beta -cypermethrin (O.3.18), theta-cypermethrin (O.3.19), zeta-cypermethrin (O.3.20), cyphenothrin (O.3.21), deltamethrin (O.3.22), empentrin (O.3.23), esfenvalerate (O .3.24), etofenprox (O.3.25), fenpropathrin (O.3.26), fenvalerate (O.3.27), flucitrinate (O.3.28), flumethrin (O.3.29), tau-fluvalinate (O.3.30), halfenprox ( O.3.31), heptafluthrin (O.3.32), imiprothrin (O.3.33), meperfluthrin (O.3.34), metofluthrin (O.3.35), momfluorothrin (O.3.36), epsilon-monfluorothrin (O.3.37), permethrin (O.3.38), phenothrin (O.3.39), pralethrin (O.3.40), profluthrin (O.3.41), pyrethrin (piretrum) (O.3.42), resmethrin (O.3.43), silafluofen (O.3.44) , tefluthrin (O.3.45), kappa-tefluthrin (O.3.46), tetramethylfluthrin (O.3.47), tetramethrin (O.3.48), tralomethrin (O.3.49), transfluthrin (O.3.50), DDT (O.3.51 ), methoxychlor (O.3.52); O.4 Nicotinic acetylcholine receptor (nAChR) agonists: acetamiprid (O.4.1), clothianidin (O.4.2), cycloxaprid (O.4.3), dinotefuran (O.4.4), imidacloprid (O.4.5), nitenpyram ( O.4.6), thiacloprid (O.4.7), thiamethoxam (O.4.8), 4,5-dihydro-N-nitro-1-(2-oxiranylmethyl)-1H-imidazol-2-amine (O.4.9 ), (2E)-1-[(6-chloropyridin-3-yl)methyl]-N'-nitro-2-pentylidenehydrazinecarboximidamide (O.4.10), 1-[(6-chloropyridin-3-yl)methyl]- 7-methyl-8-nitro-5-propoxy-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridine (O.4.11), nicotine (O.4.12), sulfoxaflor ( O.4.13), flupyradifurone (O.4.14), triflumezopyrim (O.4.15); O.5 Allosteric activators of the nicotinic acetylcholine receptor: spinosad (O.5.1), spinetoram (O.5.2); O.6 Chloride channel activators: abamectin (O.6.1), emamectin benzoate (O.6.2), ivermectin (O.6.3), lepimectin (O.6.4), milbemectin (O.6.5); O.7 Juvenile hormone imitators: hydroprene (O.7.1), cynoprene (O.7.2), methoprene (O.7.3), fenoxycarb (O.7.4), pyriproxyfen (O.7.5); O.8 Non-specific (multi-site) inhibitors: methyl bromide (O.8.1) and other alkyl halides, chloropicrin (O.8.2), sulfuryl fluoride (O.8.3), borax (O.8.4), tartar emetic (O.8.5); O.9 TRPV channel modulators of cortodonal organs: pymetrozine (O.9.1), pyrifluquinazone (O.9.2), flonicamide (O.9.3); O.10 Mite growth inhibitors: clofentezine (O.10.1), hexithiazox (O.10.2), diflovidazine (O.10.3), etoxazole (O.10.4); O.11 Microbial disruptors of insect midgut membranes: Bacillus thuringiensis, Bacillus sphaericus and the insecticidal proteins they produce: Bacillus thuringiensis subsp. Israelensis (O.11.1), Bacillus sphaericus (O.11.2), Bacillus thuringiensis subsp. aizawai (O.11.3), Bacillus thuringiensis subsp. kurstaki (O.11.4), Bacillus thuringiensis subsp. tenebrionis (O.11.5), Bt culture proteins: Cry1Ab (O.11.6), Cry1Ac (O.11.7), Cry1Fa (O.11.8), Cry2Ab (O.11.9), mCry3A (O.11.10), Cry3Ab ( O.11.11), Cry3Bb (O.11.12), Cry34/35Ab1 (O.11.13); O.12 Mitochondrial ATP synthase inhibitors: Diafentiuron (O.12.1), azocyclotine (O.12.2), cyhexatin (O.12.3), fenbutatin oxide (O.12.4), propargite (O.12.5), tetradifon (O. 12.6); O.13 Oxidative phosphorylation uncouplers through disruption of the proton gradient: chlorfenapyr (O.13.1), DNOC (O.13.2), sulfluramide (O.13.3); O.14 Nicotinic acetylcholine receptor channel (nAChR) blockers: bensultape (O.14.1), Cartape hydrochloride (O.14.2), thiocyclam (O.14.3), thiosultape sodium (O.14.4); O.15 Type 0 chitin biosynthesis inhibitors: Bistriflurom (O.15.1), chlorfluazurom (O.15.2), diflubenzuron (O.15.3), flucicloxuron (O.15.4), flufenoxuron (O.15.5), hexaflumuron (O. 15.6), lufenurom (O.15.7), novaluron (O.15.8), noviflumurom (O.15.9), teflubenzuron (O.15.10), triflumurom (O.15.11); O.16 Type 1 chitin biosynthesis inhibitors: buprofezim (O.16.1); O.17 Molting disruptors: cyromazine (O.17.1); O.18 Ecdysone receptor agonists: methoxyfenozide (O.18.1), tebufenozide (O.18.2), halofenozide (O.18.3), fufenozide (O.18.4), chromafenozide (O.18.5); O.19 Octopamine receptor agonists: amitraz (O.19.1); O.20 Mitochondrial complex III electron transport inhibitors: Hydramethylnone (O.20.1), acequinocil (O.20.2), fluacripyrim (O.20.3), bifenazate (O.20.4); O.21 Mitochondrial Complex I electron transport inhibitors: fenazaquine (O.21.1), fenpyroximate (O.21.2), pyrimidifen (O.21.3), pyridabene (O.21.4), tebufenpyrad (O.21.5), tolfenpyrad ( O.21.6), rotenone (O.21.7); O.22 Voltage-gated sodium channel blockers: indoxacarb (O.22.1), metaflumizone (O.22.2), 2-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]- N-[4-(difluoromethoxy)phenyl]-hydrazinecarboxamide (O.22.3), N-(3-chloro-2-methylphenyl)-2-[(4-chlorophenyl)-[4-[methyl(methylsulfonyl)amino]phenyl ]methylene]-hydrazinecarboxamide (O.22.4); O.23 Acetyl CoA carboxylase inhibitors: Spirodiclofen (O.23.1), spiromesifene (O.23.2), spirotetramate (O.23.3), spiropidion (O.23.4); O.24 Mitochondrial complex IV electron transport inhibitors: aluminum phosphide (O.24.1), calcium phosphide (O.24.2), phosphine (O.24.3), zinc phosphide (O.24.4), cyanide (O .24.5); O.25 Mitochondrial complex II electron transport inhibitors: cyenopyrafen (O.25.1), cyflumetofem (O.25.2); O.26 Ryanodine receptor modulators: flubendiamide (O.26.1), chlorantraniliprole (O.26.2), cyantraniliprole (O.26.3), cyclaniliprole (O.26.4), tetranyliprole (O.26.5), (R)-3- chloro-N1-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}-N2-(1-methyl-2-methylsulfonylethyl)phthalamide (O.26.6), (S)-3-chloro-N1-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}-N2-(1-methyl-2-methylsulfonylethyl)phthalamide (O.26.7), methyl-2-[3,5-dibromo-2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino) benzoyl]-1,2-dimethylhydrazinecarboxylate (O.26.8), N-[4,6-dichloro-2-[(diethyl-lambda-4-sulfanilidene)carbeamoyl]-phenyl]-2-(3-chloro-2- pyridyl)-5-(trifluoromethyl)pyrazola-3-carboxamide (O.26.9), N-[4-chloro-2-[(diethyl-lambda-4-sulfanilidene)carbeamoyl]-6-methyl-phenyl]-2- (3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazola-3-carboxamide (O.26.10), N-[4-chloro-2-[(di-2-propyl-lambda-4-sulfanilidene)carbeamoyl ]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazola-3-carboxamide (O.26.11), N-[4,6-dichloro-2-[( di-2-propyl-lambda-4-sulfanilidene)carbeamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazola-3-carboxamide (O.26.12), N-[4 ,6-dibromo-2-[(diethyl-lambda-4-sulfanilidene)carbeamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide (O.26.13) , N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloro-2-pyridinyl)-1H -pyrazole-5-carboxamide (O.26.14), 3-chloro-1-(3-chloro-2-pyridinyl)-N-[2,4-dichloro-6-[[(1-cyano-1-methylethyl) amino]carbonyl]phenyl]-1H-pyrazole-5-carboxamide (O.26.15), tetrachlorantraniliprole (O.26.16), N-[4-chloro-2-[[(1,1-dimethylethyl)amino]carbonyl]- 6-methylphenyl]-1-(3-chloro-2-pyridinyl)-3-(fluoromethoxy)-1H-pyrazole-5-carboxamide (O.26.17), cyhalodiamide (O.26.18); O.27 Cortodonal organ modulators - undefined target site: flonicamide (O.27.1); O.28. Insecticidal active compounds with unknown or uncertain mode of action: afidopyropene (O.28.1), afoxolaner (O.28.2), azadirachtin (O.28.3), amidoflumet (O.28.4), benzoximate (O.28.5), broflanilide (O. 28.6), bromopropylate (O.28.7), quinomethionate (O.28.8), cryolite (O.28.9), dichloromezothiaz (O.28.10), dicofol (O.28.11), flufenerim (O.28.12), flometoquine (O.28.13 ), fluensulfone (O.28.14), fluhexafon (O.28.15), fluopyram (O.28.16), fluralaner (O.28.17), methoxadiazone (O.28.18), piperonyl butoxide (O.28.19), piflubumide (O.28.20 ), pyridalyl (O.28.21), thioxazafen (O.28.22), 11-(4-chloro-2,6-dimethylphenyl)-12-hydroxy-1,4-dioxa-9-azadispiro[4.2.4.2]-tetradec -11-en-10-one, 3-(4'-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1-azaspiro[4.5]dec-3-en-2- one, 1-[2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl]-3-(trifluoromethyl)-1H-1,2,4-triazole-5-amine ( O.28.23), Bacillus firmus I-1582 (O.28.24), flupyrimin (O.28.25), fluazaindolizine (O.28.26), 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H -isoxazol-3-yl]-2-methyl-N-(1-oxothietan-3-yl)benzamide (O.28.27), fluxametamide (O.28.28), 5-[3-[2,6-dichloro-4 -(3,3-dichloroallyloxy)phenoxy]propoxy]-1H-pyrazole (O.28.1), 4-cyano- N-[2-cyano-5-[[2,6-dibromo-4-[1,2, 2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide (O.28.29), 4-cyano-3-[(4-cyano-2-methyl -benzoyl)amino]-N-[2,6-dichloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]-2-fluoro-benzamide (O. 28.30), N-[5-[[2-chloro-6-cyano-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl]-2-cyano -phenyl]-4- cyano-2-methyl-benzamide (O.28.31), N-[5-[[2-bromo-6-chloro-4-[2,2,2-trifluoro-1-hydroxy-1 -(trifluoromethyl)ethyl]phenyl]carboamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide (O.28.32), N-[5-[[2-bromo-6-chloro-4- [1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide (O.28.33), 4 -cyano-N-[2-cyano-5-[[2,6-dichloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl]phenyl] -2-methyl-benzamide (O.28.34), 4-cyano- N-[2-cyano-5-[[2,6-dichloro-4-[1,2,2,2-tetrafluoro-1- (trifluoromethyl )ethyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide (O.28.35), N-[5-[[2-bromo-6-chloro-4-[1,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide (O.28.36); 2-(1,3-dioxan-2-yl)-6-[2-(3-pyridinyl)-5-thiazolyl]-pyridine (O.28.37), 2-[6-[2-(5-fluoro- 3-pyridinyl)-5-thiazolyl]-2-pyridinyl]-pyrimidine (O.28.38), 2-[6-[2-(3-pyridinyl)-5-thiazolyl]-2-pyridinyl]-pyrimidine (O. 28.39), N-methylsulfonyl-6-[2-(3-pyridyl)thiazol-5-yl]pyridine-2-carboxamide (O.28.40), N-methylsulfonyl-6-[2-(3-pyridyl)thiazol- 5-yl]pyridine-2-carboxamide (O.28.41), 1-[(6-chloro-3-pyridinyl)methyl]-1,2,3,5,6,7-hexahydro-5-methoxy- 7-methyl-8-nitro-imidazo[1,2-a]pyridine (O.28.42), 1-[(6-chloropyridin-3-yl)methyl]-7-methyl-8-nitro- 1,2, 3,5,6,7-hexahydroimidazo[1,2-a]pyridin-5-ol (O.28.43), 1-isopropyl-N,5-dimethyl-N-pyridazin-4-yl-pyrazola-4 -carboxamide (O.28.44), 1-(1,2-dimethylpropyl)-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazola-4-carboxamide (O.28.45), N,5-dimethyl -N- pyridazin-4-yl-1-(2,2,2-trifluoro-1-methyl-ethyl)pyrazola-4-carboxamide (O.28.46), 1- [1-(1-cyanocyclopropyl)ethyl]- N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazola-4-carboxamide (O.28.47), N-ethyl-1-(2-fluoro-1-methyl-propyl)-5-methyl-N -pyridazin-4-yl-pyrazola-4-carboxamide (O.28.48), 1-(1,2-dimethylpropyl)-N,5-dimethyl-N-pyridazin-4-yl-pyrazola-4-carboxamide (O. 28.49), 1-[1-(1-cyanocyclopropyl)ethyl]-N,5-dimethyl-N-pyridazin-4-yl-pyrazola-4-carboxamide (O.28.50), N-methyl-1-(2- fluoro-1-methyl-propyl]-5-methyl-N-pyridazin-4-yl-pyrazola-4-carboxamide (O.28.51), 1-(4,4-difluorocyclohexyl)-N-ethyl-5-methyl- N-pyridazin-4-yl-pyrazola-4-carboxamide (O.28.52), 1-(4,4-difluorocyclohexyl)-N,5-dimethyl-N-pyridazin-4-yl-pyrazola-4-carboxamide (O .28.53), N-(1-methylethyl)-2-(3-pyridinyl)-2H-indazole-4-carboxamide (O.28.54), N-cyclopropyl- 2-(3-pyridinyl)-2H-indazole-4 -carboxamide (O.28.55), N-cyclohexyl-2-(3-pyridinyl)- 2H-indazole-4-carboxamide (O.28.56), 2-(3-pyridinyl)-N-(2,2,2- trifluoroethyl)-2H- indazole-4-carboxamide (O.28.57), 2-(3-pyridinyl)-N-[(tetrahydro-2-furanyl)methyl]- 2H-indazole-5-carboxamide (O.28.58 ), methyl 2-[[2-(3-pyridinyl)-2H-indazol-5-yl]carbonyl]hydrazinecarboxylate (O.28.59), N-[(2,2-difluorocyclopropyl)methyl]-2-(3- pyridinyl)-2H-indazole-5-carboxamide (O.28.60), N-(2,2-difluoropropyl)-2-(3-pyridinyl)-2H-indazole-5-carboxamide (O.28.61), 2-( 3-pyridinyl)-N-(2-pyrimidinylmethyl)-2H-indazole-5-carboxamide (O.28.62), N-[(5-methyl-2-pyrazinyl)methyl]-2-(3-pyridinyl)-2H -indazole-5-carboxamide (O.28.63), ticlopyrazoflor (O.28.64), sarolaner (O.28.65), lotilaner (O.28.66), N-[4-chloro-3- [[(phenylmethyl)amino]carbonyl ]phenyl]-1-methyl-3-(1,1,2,2,2-pentafluoroethyl)-4- (trifluoromethyl)-1H-pyrazole-5-carboxamide (O.28.67), M.UN.22a 2- (3-ethylsulfonyl-2-pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine (O.28.68), 2-[3-ethylsulfonyl-5-(trifluoromethyl)-2-pyridyl ]-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine (O.28.69), 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3 -yl]-N-[(4R)-2-ethyl-3-oxo-isoxazolidin-4-yl]-2-methyl-benzamide (O.28.70), 4-[5-(3,5-dichloro-4 -fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-N-[(4R)-2-ethyl-3-oxo-isoxazolidin-4-yl]-2-methyl-benzamide (O .28.71), N-[4-chloro-3-(cyclopropylcarbamoyl)phenyl]-2-methyl-5-(1,1,2,2,2-pentafluoroethyl)-4-(trifluoromethyl)pyrazole-3-carboxamide ( O.28.72), N-[4-chloro-3-[(1-cyanocyclopropyl)carbamoyl]phenyl]-2-methyl-5-(1,1,2,2,2-pentafluoroethyl)-4-(trifluoromethyl) pyrazole-3-carboxamide (O.28.73), acinonapyr (O.28.74), benzpyrimoxan (O.28.75), chloro-N-(1-cyanocyclopropyl)-5-[1-[2-methyl-5- (1, 1,2,2,2-pentafluoroethyl)-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide (O.28.76), oxazosulfil (O.28.77), [(2S,3R,4R, 5S,6S)-3,5-dimethoxy-6-methyl-4-propoxy-tetrahydropyran-2-yl]-N-[4-[1-[4-(trifluoromethoxy)phenyl]-1,2,4 -triazol-3-yl]phenyl]carbamate (O.28.78), [(2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyl-tetrahydropyran-2-yl]N -[4-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]carbamate (O.28.79), [(2S,3R,4R,5S,6S)- 3,5-dimethoxy-6-methyl-4-propoxy-tetrahydropyran-2-yl]-N-[4-[1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]- 1,2,4-triazol-3-yl]phenyl]carbamate (O.28.80), [(2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyl-tetrahydropyran- 2-yl]-N-[4-[1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]carbamate (O. 28.81), (2Z)-3-(2-isopropylphenyl)-2-[(E)-[4-[1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1,2 ,4-triazol-3-yl]phenyl]methylenehydrazono]thiazolidin-4-one (O.28.82).

[00210] The active substances mentioned as component 2, their preparations and their activities, for example, against harmful fungi are known (cf.: http://www.alanwood.net/pesticides/); these substances are commercially available. The compounds described by the IUPAC nomenclature, their preparations and their pesticidal activities are also known (cf. Can. J. Plant Sci. 48(6), 587-94, 1968; patents EP-A 141 317; EP-A 152 031 EP-A 226 917; EP-A 1 028 125; 648; EP 1 122 244, JP 2002316902; 19650197; 10021412; 27783; WO 00/29404; WO 00/46148; WO 00/65913; 14103; WO 03/16286; WO 03/53145; WO 03/61388; 125/63721; WO 05/87772; WO 06/87325; 028657, WO 12/168188, WO 07/006670, WO 11/77514; 13/ 010862, WO 13/127704, WO 13/024009, WO 13/24010, WO 13/047441, WO 13/162072, WO 13/092224, WO 11/135833, patents CN 1907024, CN 1456054, 103387541, CN 1309897, document WO 12/84812, patent CN 1907024, documents WO 09094442, WO 14/60177, WO 13/116251, WO 08/013622, WO 15/65922, WO 94/01546, patent EP 2865265, documents WO 07/129454 , W.O. 12/165511, WO 11/081174, WO 13/47441, JP patents 2015089883, JP 2015120675, WO documents 2015119246, WO 2011135827, WO 2012084812).

[00211] The present invention, furthermore, refers to agrochemical compositions comprising a mixture of at least one compound I (component 1) and at least one additional active substance useful for plant protection, for example, selected from the groups A) to O) (component 2), in particular, an additional fungicide, for example, one or more fungicides of groups A) to K), as described above and, if desirable, a suitable solvent or solid carrier. These mixtures are of particular interest since many of them at the same application rate show higher efficiencies against harmful fungi. Furthermore, combating harmful fungi with a mixture of compounds I and at least one fungicide from groups A) to K) as described above is more effective than combating fungi with individual compounds I or individual fungicides from groups A) to K ).

[00212] By applying compounds I, together with at least one active substance from groups A) to O), a synergistic effect can be obtained, that is, more is obtained than the simple addition of individual effects (synergistic mixtures).

[00213] This can be obtained by applying compounds I and at least one additional active substance simultaneously, either together (for example, as a tank mix) or separately, or successively, wherein the time interval between individual applications is selected to ensure that the active substance applied first still occurs at the site of action in a sufficient quantity at the time of application of the additional active substance(s). The order of application is not essential to the work of the present invention.

[00214] When applying compound I and a pesticide II sequentially, the time between both applications can vary, for example, between 2 hours to 7 days. A wider range is also possible, ranging from 0.25 hour to 30 days, preferably from 0.5 hour to 14 days, particularly from 1 hour to 7 days or from 1.5 hours to 5 days, even more preferably from 2 hours to 1 day.

[00215] In binary mixtures and compositions according to the invention, the weight ratio of component 1) and component 2) generally depends on the properties of the active components used, generally being in the range of 1:10,000 to 10,000:1 , is often in the range of 1:100 to 100:1, regularly in the range of 1:50 to 50:1, preferably in the range of 1:20 to 20:1, more preferably in the range of 1:10 to 10: 1, even more preferably in the range of 1:4 to 4:1 and, in particular, in the range of 1:2 to 2:1.

[00216] According to further embodiments of binary mixtures and compositions, the weight ratio of component 1) and component 2) is generally in the range of 1:10,000 to 1:1, often in the range of 100:1 to 1:1, regularly in the range of 50:1 to 1:1, preferably in the range of 20:1 to 1:1, more preferably in the range of 10:1 to 1:1, even more preferably in the range of 4:1 to 1:1 and, in particular, in the range of 2:1 to 1:1.

[00217] According to further embodiments of binary mixtures and compositions, the weight ratio of component 1) and component 2) is generally in the range of 1:1 to 1:1000, often in the range of 1:1 to 1:100, regularly in the range of 1:1 to 1:50, preferably in the range of 1:1 to 1:20, more preferably in the range of 1:1 to 1:10, even more preferably in the range of 1:1 to 1:4 and, in particular, in the range of 1:1 to 1:2.

[00218] In ternary mixtures, that is, compositions according to the invention comprising component 1) and component 2) and a compound III (component 3), the ratio, by weight, of component 1) and component 2 ) depends on the properties of the active substances used, is generally in the range of 1:100 to 100:1, regularly in the range of 1:50 to 50:1, preferably in the range of 1:20 to 20:1, more preferably in the range from 1:10 to 10:1 and in particular in the range of 1:4 to 4:1, and the ratio, by weight, of component 1) and component 3) generally in the range of 1:100 to 100:1 , regularly in the range of 1:50 to 50:1, preferably in the range of 1:20 to 20:1, more preferably in the range of 1:10 to 10:1 and, in particular in the range of 1:4 to 4: 1.

[00219] Any additional active components are, if desired, added to component 1) in a ratio of 20:1 to 1:20.

[00220] These ratios are also suitable for inventive mixtures applied by seed treatment.

[00221] Consequently, the present invention, furthermore, refers to mixtures comprising a compound of formula I (component 1, a group represented by the expression “(I)”) and a pesticide II (component 2), wherein pesticide II is an active ingredient selected from groups A) to O) defined above.

[00222] Additional embodiments B-1 to B-684 listed in Table B refer to mixtures comprising as active components one of the compounds of formula I individualized in the present specification, which is selected from the group of compounds I.A.A-1 to I.A.A-72, I.B.A-1 to I.B.A-72, I.C.A-1 to I.C.A-72, as defined in Tables 1 to 3 or from compounds Ex-1 to Ex-31, as defined in tables C.1, C .2 and C.3 (component 1, a group represented by the expression “(I)”), and a pesticide II selected from groups A) to O) as defined in the present application (component 2, e.g., (A .1.1) or azoxystrobin, in realization B-1).

[00223] Preferably, the compositions described in Table B comprise the active components in synergistically effective amounts. TABLE B B-1: (I) + (A.1.1), B-2: (I) + (A.1.2), B-3: (I) + (A.1.3), B-4: (I ) + (A.1.4), B-5: (I) + (A.1.5), B-6: (I) + (A.1.6), B-7: (I) + (A.1.7), B-8: (I) + (A.1.8), B-9: (I) + (A.1.9), B-10: (I) + (A.1.10), B-11: (I) + (A.1.11), B-12: (I) + (A.1.12), B-13: (I) + (A.1.13), B-14: (I) + (A.1.14), B- 15: (I) + (A.1.15), B-16: (I) + (A.1.16), B- 17: (I) + (A.1.17), B-18: (I) + (A .1.18), B-19: (I) + (A.1.19), B-20: (I) + (A.1.20), B-21: (I) + (A.1.21), B-22: (I) + (A.1.21a), B-23: (I) + (A.1.22), B-24: (I) + (A.1.25), B-25: (I) + (A. 1.34), B-26: (I) + (A.1.35), B-27: (I) + (A.1.36), B-28: (I) + (A.1.37), B-29: ( I) + (A.1.38), B-30: (I) + (A.2.1), B-31: (I) + (A.2.2), B- 32: (I) + (A.2.3) , B-33: (I) + (A.2.4), B-34: (I) + (A.2.5), B-35: (I) + (A.3.1), B- 36: (I) + (A.3.2), B-37: (I) + (A.3.3), B-38: (I) + (A.3.4), B-39: (I) + (A.3.5), B - 40: (I) + (A.3.6), B-41: (I) + (A.3.7), B-42: (I) + (A.3.8), B-43: (I) + ( A.3.9), B- 44: (I) + (A.3.10), B-45: (I) + (A.3.11), B-46: (I) + (A.3.12), B-47 : (I) + (A.3.13), B-48: (I) + (A.3.14), B-49: (I) + (A.3.15), B-50: (I) + (A. 3.16), B-51: (I) + (A.3.17), B-52: (I) + (A.3.18), B-53: (I) + (A.3.19), B-54: ( I) + (A.3.20), B-55: (I) + (A.3.21), B-56: (I) + (A.3.22), B-57: (I) + (A.3.23) , B-58: (I) + (A.3.24), B- 59: (I) + (A.3.25), B-60: (I) + (A.3.26), B-61: (I) + (A.3.27), B-62: (I) + (A.3.28), B-63: (I) + (A.3.30), B-64: (I) + (A.3.31), B -65: (I) + (A.3.32), B-66: (I) + (A.3.33), B-67: (I) + (A.3.34), B-68: (I) + ( A.3.35), B-69: (I) + (A.3.36), B-70: (I) + (A.3.37), B-71: (I) + (A.3.38), B-72 : (I) + (A.3.39), B-73: (I) + (A.4.1), B- 74: (I) + (A.4.2), B-75: (I) + (A. 4.3), B-76: (I) + (A.4.4), B-77: (I) + (A.4.5), B- 78: (I) + (A.4.6), B-79: ( I) + (A.4.7), B-80: (I) + (A.4.8), B-81: (I) + (A.4.9), B- 82: (I) + (A.4.10) , B-83: (I) + (A.4.11), B-84: (I) + (A.4.12), B-85: (I) + (B.1.1), B-86: (I) + (B.1.2), B-87: (I) + (B.1.3), B-88: (I) + (B.1.4), B-89: (I) + (B.1.5), B -90: (I) + (B.1.6), B-91: (I) + (B.1.7), B-92: (I) + (B.1.8), B-93: (I) + ( B.1.9), B-94: (I) + (B.1.10), B-95: (I) + (B.1.11), B-96: (I) + (B.1.12), B-97 : (I) + (B.1.13), B-98: (I) + (B.1.14), B-99: (I) + (B.1.15), B-100: (I) + (B. 1.16), B- 101: (I) + (B.1.17), B-102: (I) + (B.1.18), B-103: (I) + (B.1.19), B-104: ( I) + (B.1.20), B-105: (I) + (B.1.21), B-106: (I) + (B.1.22), B-107: (I) + (B.1.23) , B- 108: (I) + (B.1.24), B-109: (I) + (B.1.25), B-110: (I) + (B.1.26), B-111: (I) + (B.1.27), B-112: (I) + (B.1.28), B-113: (I) + (B.1.29), B-114: (I) + (B.1.30), B - 115: (I) + (B.1.31), B-116: (I) + (B.1.32), B-117: (I) + (B.1.37), B-118: (I) + ( B.1.38), B-119: (I) + (B.1.39), B-120: (I) + (B.1.40), B-121: (I) + (B.1.41), B- 122 : (I) + (B.1.42), B-123: (I) + (B.1.43), B-124: (I) + (B.1.44), B-125: (I) + (B. 1.45), B-126: (I) + (B.1.46), B-127: (I) + (B.1.47), B-128: (I) + (B.1.48), B- 129: ( I) + (B.1.49), B-130: (I) + (B.1.50), B-131: (I) + (B.1.51), B-132: (I) + (B.1.52) , B-133: (I) + (B.2.1), B-134: (I) + (B.2.2), B-135: (I) + (B.2.3), B-136: (I) + (B.2.4), B-137: (I) + (B.2.5), B-138: (I) + (B.2.6), B-139: (I) + (B.2.7), B - 140: (I) + (B.2.8), B-141: (I) + (B.3.1), B-142: (I) + (B.4.1), B-143: (I) + ( C.1.1), B-144: (I) + (C.1.2), B-145: (I) + (C.1.3), B-146: (I) + (C.1.4), B-147 : (I) + (C.1.5), B-148: (I) + (C.1.6), B-149: (I) + (C.1.7), B-150: (I) + (C. 2.1), B-151: (I) + (C.2.2), B-152: (I) + (C.2.3), B-153: (I) + (C.2.4), B-154: ( I) + (C.2.5), B- 155: (I) + (C.2.6), B-156: (I) + (C.2.7), B-157: (I) + (C.2.8) , B-158: (I) + (D.1.1), B-159: (I) + (D.1.2), B-160: (I) + (D.1.3), B-161: (I) + (D.1.4), B-162: (I) + (D.1.5), B-163: (I) + (D.1.6), B-164: (I) + (D.1.7), B -165: (I) + (D.1.8), B-166: (I) + (D.1.9), B-167: (I) + (D.1.10), B-168: (I) + ( D.1.11), B-169: (I) + (D.1.12), B-170: (I) + (D.1.13), B-171: (I) + (D.1.14), B-172 : (I) + (D.1.15), B-173: (I) + (D.1.16), B-174: (I) + (D.2.1), B-175: (I) + (D. 2.2), B-176: (I) + (D.2.3), B-177: (I) + (D.2.4), B-178: (I) + (D.2.5), B-179: ( I) + (D.2.6), B-180: (I) + (D.2.7), B- 181: (I) + (E.1.1), B-182: (I) + (E.1.2) , B-183: (I) + (E.1.3), B-184: (I) + (E.2.1), B-185: (I) + (E.2.2), B-186: (I) + (E.2.3), B-187: (I) + (E.2.4), B-188: (I) + (E.2.5), B-189: (I) + (E.2.6), B -190: (I) + (F.1.1), B-191: (I) + (F.1.2), B-192: (I) + (F.1.3), B-193: (I) + ( F.1.4), B-194: (I) + (F.1.5), B-195: (I) + (F.2.1), B- 196: (I) + (G.1.1), B-197 : (I) + (G.1.2), B-198: (I) + (G.1.3), B-199: (I) + (G.1.4), B-200: (I) + (G. 2.1), B-201: (I) + (G.2.2), B-202: (I) + (G.2.3), B-203: (I) + (G.2.4), B-204: ( I) + (G.2.5), B-205: (I) + (G.2.6), B-206: (I) + (G.2.7), B- 207: (I) + (G.3.1) , B-208: (I) + (G.3.2), B-209: (I) + (G.3.3), B-210: (I) + (G.3.4), B-211: (I) + (G.3.5), B-212: (I) + (G.3.6), B-213: (I) + (G.3.7), B-214: (I) + (G.4.1), B -215: (I) + (G.5.1), B-216: (I) + (G.5.2), B-217: (I) + (G.5.3), B- 218: (I) + ( G.5.4), B-219: (I) + (G.5.5), B-220: (I) + (G.5.6), B-221: (I) + (G.5.7), B-222 : (I) + (G.5.8), B-223: (I) + (G.5.9), B-224: (I) + (G.5.10), B- 225: (I) + (G. 5.11), B-226: (I) + (H.1.1), B-227: (I) + (H.1.2), B-228: (I) + (H.1.3), B-229: ( I) + (H.1.4), B-230: (I) + (H.1.5), B-231: (I) + (H.1.6), B-232: (I) + (H.1.7) , B-233: (I) + (H.2.1), B-234: (I) + (H.2.2), B-235: (I) + (H.2.3), B- 236: (I) + (H.2.4), B-237: (I) + (H.2.5), B-238: (I) + (H.2.6), B-239: (I) + (H.2.7), B -240: (I) + (H.2.8), B-241: (I) + (H.2.9), B-242: (I) + (H.3.1), B-243: (I) + ( H.3.2), B-244: (I) + (H.3.3), B-245: (I) + (H.3.4), B-246: (I) + (H.3.5), B-247 : (I) + (H.3.6), B-248: (I) + (H.3.7), B-249: (I) + (H.3.8), B-250: (I) + (H. 3.9), B- 251: (I) + (H.3.10), B-252: (I) + (H.3.11), B-253: (I) + (H.4.1), B-254: ( I) + (H.4.2), B-255: (I) + (H.4.3), B-256: (I) + (H.4.4), B-257: (I) + (H.4.5) , B-258: (I) + (H.4.6), B-259: (I) + (H.4.7), B-260: (I) + (H.4.8), B-261: (I) + (H.4.9), B- 262: (I) + (H.4.10), B-263: (I) + (I.1.1), B-264: (I) + (I.1.2), B -265: (I) + (I.2.1), B-266: (I) + (I.2.2), B-267: (I) + (I.2.3), B-268: (I) + ( I.2.4), B-269: (I) + (I.2.5), B-270: (I) + (J.1.1), B-271: (I) + (J.1.2), B-272 : (I) + (J.1.3), B-273: (I) + (J.1.4), B-274: (I) + (J.1.5), B-275: (I) + (J. 1.6), B-276: (I) + (J.1.7), B-277: (I) + (J.1.8), B-278: (I) + (J.1.9), B-279: ( I) + (J.1.10), B-280: (I) + (K.1.1), B-281: (I) + (K.1.2), B-282: (I) + (K.1.3) , B-283: (I) + (K.1.4), B-284: (I) + (K.1.5), B- 285: (I) + (K.1.6), B-286: (I) + (K.1.7), B-287: (I) + (K.1.8), B-288: (I) + (K.1.9), B-289: (I) + (K.1.10), B -290: (I) + (K.1.11), B-291: (I) + (K.1.12), B-292: (I) + (K.1.13), B-293: (I) + ( K.1.14), B-294: (I) + (K.1.15), B-295: (I) + (K.1.16), B- 296: (I) + (K.1.17), B-297 : (I) + (K.1.18), B-298: (I) + (K.1.19), B-299: (I) + (K.1.20), B-300: (I) + (K. 1.21), B-301: (I) + (K.1.22), B-302: (I) + (K.1.23), B- 303: (I) + (K.1.24), B-304: ( I) + (K.1.25), B-305: (I) + (K.1.26), B-306: (I) + (K.1.27), B-307: (I) + (K.1.28) , B-308: (I) + (K.1.29), B-309: (I) + (K.1.30), B- 310: (I) + (K.1.31), B-311: (I) + (K.1.32), B-312: (I) + (K.1.33), B-313: (I) + (K.1.34), B-314: (I) + (K.1.35), B -315: (I) + (K.1.36), B-316: (I) + (K.1.37), B- 317: (I) + (K.1.38), B-318: (I) + ( K.1.39), B-319: (I) + (K.1.40), B-320: (I) + (K.1.41), B-321: (I) + (K.1.42), B-322 : (I) + (K.1.43), B-323: (I) + (K.1.44), B- 324: (I) + (K.1.45), B-325: (I) + (K. 1.46), B-326: (I) + (K.1.47), B-327: (I) + (K.1.48), B-328: (I) + (K.1.49), B-329: ( I) + (K.1.50), B-330: (I) + (K.1.51), B- 331: (I) + (K.1.52), B-332: (I) + (K.1.53) , B-333: (I) + (K.1.54), B-334: (I) + (O.1.1), B-335: (I) + (O.1.2), B-336: (I) + (O.1.3), B-337: (I) + (O.1.4), B-338: (I) + (O.1.5), B-339: (I) + (O.1.6), B -340: (I) + (O.1.7), B-341: (I) + (O.1.8), B- 342: (I) + (O.1.9), B-343: (I) + ( O.1.10), B-344: (I) + (O.1.11), B-345: (I) + (O.1.12), B-346: (I) + (O.1.13), B-347 : (I) + (O.1.14), B-348: (I) + (O.1.15), B- 349: (I) + (O.1.16), B-350: (I) + (O. 1.17), B-351: (I) + (O.1.18), B-352: (I) + (O.1.19), B-353: (I) + (O.1.20), B-354: ( I) + (O.1.21), B-355: (I) + (O.1.22), B- 356: (I) + (O.1.23), B-357: (I) + (O.1.24) , B-358: (I) + (O.1.25), B-359: (I) + (O.1.26), B-360: (I) + (O.1.27), B-361: (I) + (O.1.28), B-362: (I) + (O.1.29), B- 363: (I) + (O.1.30), B-364: (I) + (O.1.31), B -365: (I) + (O.1.32), B-366: (I) + (O.1.33), B-367: (I) + (O.1.34), B-368: (I) + ( O.1.35), B-369: (I) + (O.1.36), B- 370: (I) + (O.1.37), B-371: (I) + (O.1.38), B-372 : (I) + (O.1.39), B-373: (I) + (O.1.40), B-374: (I) + (O.1.41), B-375: (I) + (O. 1.42), B-376: (I) + (O.1.43), B- 377: (I) + (O.1.44), B-378: (I) + (O.1.45), B-379: ( I) + (O.1.46), B-380: (I) + (O.1.47), B-381: (I) + (O.1.48), B-382: (I) + (O.1.49) , B-383: (I) + (O.1.50), B- 384: (I) + (O.1.51), B-385: (I) + (O.1.52), B-386: (I) + (O.1.53), B-387: (I) + (O.1.54), B-388: (I) + (O.1.55), B-389: (I) + (O.1.56), B -390: (I) + (O.1.57), B- 391: (I) + (O.1.58), B-392: (I) + (O.1.59), B-393: (I) + ( O.1.60), B-394: (I) + (O.1.61), B-395: (I) + (O.1.62), B-396: (I) + (O.1.63), B-397 : (I) + (O.1.64), B- 398: (I) + (O.1.65), B-399: (I) + (O.1.66), B-400: (I) + (O. 1.67), B-401: (I) + (O.1.68), B-402: (I) + (O.1.69), B-403: (I) + (O.1.70), B-404: ( I) + (O.1.71), B- 405: (I) + (O.1.72), B-406: (I) + (O.1.73), B-407: (I) + (O.1.74) , B-408: (I) + (O.1.75), B-409: (I) + (O.1.76), B-410: (I) + (O.1.77), B-411: (I) + (O.1.78), B- 412: (I) + (O.1.79), B-413: (I) + (O.1.80), B-414: (I) + (O.1.81), B -415: (I) + (O.1.82), B-416: (I) + (O.1.83), B-417: (I) + (O.1.84), B-418: (I) + ( O.1.85), B- 419: (I) + (O.1.86), B-420: (I) + (O.1.87), B-421: (I) + (O.1.88), B-422 : (I) + (O.1.89), B-423: (I) + (O.1.90), B-424: (I) + (O.1.91), B-425: (I) + (O. 2.1), B- 426: (I) + (O.2.2), B-427: (I) + (O.2.3), B-428: (I) + (O.2.4), B-429: ( I) + (O.2.5), B-430: (I) + (O.2.6), B-431: (I) + (O.2.7), B-432: (I) + (O.3.1) , B-433: (I) + (O.3.2), B-434: (I) + (O.3.3), B-435: (I) + (O.3.4), B-436: (I) + (O.3.5), B- 437: (I) + (O.3.6), B-438: (I) + (O.3.7), B-439: (I) + (O.3.8), B -440: (I) + (O.3.9), B-441: (I) + (O.3.10), B-442: (I) + (O.3.11), B-443: (I) + ( O.3.12), B- 444: (I) + (O.3.13), B-445: (I) + (O.3.14), B-446: (I) + (O.3.15), B-447 : (I) + (O.3.16), B-448: (I) + (O.3.17), B-449: (I) + (O.3.18), B-450: (I) + (O. 3.19), B- 451: (I) + (O.3.20), B-452: (I) + (O.3.21), B-453: (I) + (O.3.22), B-454: ( I) + (O.3.23), B-455: (I) + (O.3.24), B-456: (I) + (O.3.25), B-457: (I) + (O.3.26) , B- 458: (I) + (O.3.27), B-459: (I) + (O.3.28), B-460: (I) + (O.3.29), B-461: (I) + (O.3.30), B-462: (I) + (O.3.31), B-463: (I) + (O.3.32), B-464: (I) + (O.3.33), B - 465: (I) + (O.3.34), B-466: (I) + (O.3.35), B-467: (I) + (O.3.36), B-468: (I) + ( O.3.37), B-469: (I) + (O.3.38), B-470: (I) + (O.3.39), B-471: (I) + (O.3.40), B- 472 : (I) + (O.3.41), B-473: (I) + (O.3.42), B-474: (I) + (O.3.43), B-475: (I) + (O. 3.44), B-476: (I) + (O.3.45), B-477: (I) + (O.3.46), B-478: (I) + (O.3.47), B- 479: ( I) + (O.3.48), B-480: (I) + (O.3.49), B-481: (I) + (O.3.50), B-482: (I) + (O.3.51) , B-483: (I) + (O.3.52), B-484: (I) + (O.4.1), B-485: (I) + (O.4.2), B- 486: (I) + (O.4.3), B-487: (I) + (O.4.4), B-488: (I) + (O.4.5), B-489: (I) + (O.4.6), B -490: (I) + (O.4.7), B-491: (I) + (O.4.8), B-492: (I) + (O.4.9), B-493: (I) + ( O.4.10), B-494: (I) + (O.4.11), B-495: (I) + (O.4.12), B-496: (I) + (O.4.13), B-497 : (I) + (O.4.14), B-498: (I) + (O.4.15), B-499: (I) + (O.5.1), B- 500: (I) + (O. 5.2), B-501: (I) + (O.6.1), B-502: (I) + (O.6.2), B-503: (I) + (O.6.3), B-504: ( I) + (O.6.4), B-505: (I) + (O.6.5), B-506: (I) + (O.7.1), B-507: (I) + (O.7.2) , B-508: (I) + (O.7.3), B-509: (I) + (O.7.4), B-510: (I) + (O.7.5), B- 511: (I) + (O.8.1), B-512: (I) + (O.8.2), B-513: (I) + (O.8.3), B-514: (I) + (O.8.4), B -515: (I) + (O.8.5), B-516: (I) + (O.9.1), B-517: (I) + (O.9.2), B-518: (I) + ( O.9.3), B-519: (I) + (O.10.1), B-520: (I) + (O.10.2), B-521: (I) + (O.10.3), B-522 : (I) + (O.10.4), B-523: (I) + (O.11.1), B-524: (I) + (O.11.2), B-525: (I) + (O. 11.3), B-526: (I) + (O.11.4), B-527: (I) + (O.11.5), B-528: (I) + (O.11.6), B- 529: ( I) + (O.11.7), B-530: (I) + (O.11.8), B-531: (I) + (O.11.9), B-532: (I) + (O.11.10) , B-533: (I) + (O.11.11), B-534: (I) + (O.11.12), B-535: (I) + (O.11.13), B-536: (I) + (O.12.1), B-537: (I) + (O.12.2), B-538: (I) + (O.12.3), B-539: (I) + (O.12.4), B -540: (I) + (O.12.5), B-541: (I) + (O.12.6), B-542: (I) + (O.13.1), B-543: (I) + ( O.13.2), B-544: (I) + (O.13.3), B-545: (I) + (O.14.1), B- 546: (I) + (O.14.2), B-547 : (I) + (O.14.3), B-548: (I) + (O.14.4), B-549: (I) + (O.15.1), B-550: (I) + (O. 15.2), B-551: (I) + (O.15.3), B-552: (I) + (O.15.4), B- 553: (I) + (O.15.5), B-554: ( I) + (O.15.6), B-555: (I) + (O.15.7), B-556: (I) + (O.15.8), B-557: (I) + (O.15.9) , B-558: (I) + (O.15.10), B-559: (I) + (O.15.11), B-560: (I) + (O.16.1), B-561: (I) + (O.17.1), B-562: (I) + (O.18.1), B-563: (I) + (O.18.2), B-564: (I) + (O.18.3), B -565: (I) + (O.18.4), B-566: (I) + (O.18.5), B- 567: (I) + (O.19.1), B-568: (I) + ( O.20.1), B-569: (I) + (O.20.2), B-570: (I) + (O.20.3), B-571: (I) + (O.20.4), B-572 : (I) + (O.21.1), B-573: (I) + (O.21.2), B- 574: (I) + (O.21.3), B-575: (I) + (O. 21.4), B-576: (I) + (O.21.5), B-577: (I) + (O.21.6), B-578: (I) + (O.21.7), B-579: ( I) + (O.22.1), B-580: (I) + (O.22.2), B- 581: (I) + (O.22.3), B-582: (I) + (O.22.4) , B-583: (I) + (O.23.1), B-584: (I) + (O.23.2), B-585: (I) + (O.23.3), B-586: (I) + (O.23.4), B-587: (I) + (O.24.1), B- 588: (I) + (O.24.2), B-589: (I) + (O.24.3), B -590: (I) + (O.24.4), B-591: (I) + (O.24.5), B-592: (I) + (O.25.1), B-593: (I) + ( O.25.2), B-594: (I) + (O.26.1), B- 595: (I) + (O.26.2), B-596: (I) + (O.26.3), B-597 : (I) + (O.26.4), B-598: (I) + (O.26.5), B-599: (I) + (O.26.6), B-600: (I) + (O. 26.7), B-601: (I) + (O.26.8), B- 602: (I) + (O.26.9), B-603: (I) + (O.26.10), B-604: ( I) + (O.26.11), B-605: (I) + (O.26.12), B-606: (I) + (O.26.13), B-607: (I) + (O.26.14) , B-608: (I) + (O.26.15), B-609: (I) + (O.26.16), B-610: (I) + (O.26.17), B-611: (I) + (O.26.18), B-612: (I) + (O.27.1), B-613: (I) + (O.28.1), B-614: (I) + (O.28.2), B -615: (I) + (O.28.3), B-616: (I) + (O.28.4), B-617: (I) + (O.28.5), B-618: (I) + ( O.28.7), B-619: (I) + (O.28.8), B-620: (I) + (O.28.9), B-621: (I) + (O.28.10), B-622 : (I) + (O.28.11), B-623: (I) + (O.28.12), B-624: (I) + (O.28.13), B-625: (I) + (O. 28.14), B-626: (I) + (O.28.15), B-627: (I) + (O.28.16), B-628: (I) + (O.28.17), B-629: ( I) + (O.28.18), B-630: (I) + (O.28.19), B-631: (I) + (O.28.20), B-632: (I) + (O.28.21) , B-633: (I) + (O.28.22), B-634: (I) + (O.28.23), B-635: (I) + (O.28.24), B-636: (I) + (O.28.25), B-637: (I) + (O.28.26), B-638: (I) + (O.28.27), B-639: (I) + (O.28.28), B -640: (I) + (O.28.29), B-641: (I) + (O.28.30), B-642: (I) + (O.28.31), B-643: (I) + ( O.28.42), B-644: (I) + (O.28.43), B-645: (I) + (O.28.44), B-646: (I) + (O.28.45), B-647 : (I) + (O.28.46), B-648: (I) + (O.28.47), B-649: (I) + (O.28.48), B-650: (I) + (O. 28.49), B-651: (I) + (O.28.50), B-652: (I) + (O.28.51), B-653: (I) + (O.28.52), B-654: ( I) + (O.28.53), B-655: (I) + (O.28.54), B-656: (I) + (O.28.55), B-657: (I) + (O.28.56) , B-658: (I) + (O.28.57), B-659: (I) + (O.28.58), B-660: (I) + (O.28.59), B-661: (I) + (O.28.60), B-662: (I) + (O.28.61), B-663: (I) + (O.28.62), B-664: (I) + (O.28.63), B -665: (I) + (O.28.64), B-666: (I) + (O.28.65), B-667: (I) + (O.28.66), B-668: (I) + ( O.28.67), B-669: (I) + (O.28.68), B-670: (I) + (O.28.69), B-671: (I) + (O.28.70), B-672 : (I) + (O.28.71), B-673: (I) + (O.28.72), B-674: (I) + (O.28.73), B-675: (I) + (O. 28.74), B-676: (I) + (O.28.75), B-677: (I) + (O.28.76), B-678: (I) + (O.28.77), B-679: ( I) + (O.28.78), B-680: (I) + (O.28.79), B-681: (I) + (O.28.80), B-682: (I) + (O.28.81) , B-683: (I) + (O.28.82), B-684: (I) + (A.3.29).

[00224] Mixtures of active substances that can be prepared as compositions comprising, in addition to the active ingredients, at least one inert (auxiliary) ingredient by usual means, for example, by means indicated for compositions of compounds I.

[00225] With regard to the usual ingredients of these compositions, reference is made to the explanations given for the compositions containing compounds I.

[00226] The mixtures of active substances according to the present invention are suitable as fungicides, as are the compounds of formula I. They are distinguished by excellent effectiveness against a broad spectrum of phytopathogenic fungi, especially from the classes of Ascomycetes, Basidiomycetes, Deuteromycetes and Peronosporomycetes (syn. Oomycetes). Furthermore, explanations are cited in relation to the fungicidal activity of the compounds and compositions containing compounds I, respectively.

I. EXAMPLES OF SYNTHESIS I.1 COMPOUNDS OF FORMULA EX-1 TO EX-5 CAN BE PREPARED BY ACCORDING TO THE METHODS DESCRIBED BELOW 1.1.1 SYNTHESIS OF 4-VINYLBENZONITRILE

[00227] To a solution of 4-bromobenzonitrile (58.0 g, 318 mmol) in a mixture of propan-2-ol/water (600 mL/300 mL) was added (potassium vinyltrifluoroborate (42.7 g, 318 mmol), triethylamine (96.7 g, 956 mmol) and [1,1'-bis(dichloropaladium diphenylphosphine)ferrocene](II) (5.22 g, 6.37 mmol) at 25°C. The reaction was stirred at 100°C under a nitrogen atmosphere for 16 hours. The reaction mixture was concentrated and extracted with methyl tert-butyl ether. The organic layers were combined and concentrated. titer (26.0 g, 63%) as a yellow oil. 1H NMR (CDCl3, 400 MHz): δ [ppm] = 5.41 (d, 1 H), 5.84 (d, 1 H), 6.69 (dd, 1 H), 7.44 (d, 2 H), 7.52 - 7.62 (m, 2 H).

1.1.2 SYNTHESIS OF N-HYDROXY-4-VINYL-BENZAMIDINE

[00228] To a solution of 4-vinylbenzonitrile (5.0 g, 38.7 mmol) in ethanol (50 mL) hydroxylamine hydrochloride (5.4 g, 77.4 mmol) and triethylamine (11.8 g) were added. , 116.1 mmol). Then, the reaction was stirred at 70°C for 8 hours. The mixture was concentrated and the residue was washed with water. Then, the solid was concentrated to provide the title compound (2.7 g, 43.0%) as a white solid. 1H NMR (CDCl3, 400 MHz): δ [ppm] = 7.72 (d, 2H), 7.57 (d, 2H), 6.86 (dd, 1H), 5.94 (d, 1H), 5.39 (d, 1H), 3.71 (q, 1H).

1.1.3 SYNTHESIS OF 5-(TRIFLUOROMETHYL)-3-(4-VINYLPHENYL)-1,2,4-OXADIAZOLE

[00229] To a solution of N'-hydroxy-4-vinyl-benzamidine (1.0 g, 6.17 mmol) in N,N-dimethylacetamide (20 mL) trifluoroacetic anhydride (2.6 g, 12.0 mL) was added. 3 mmol) by dripping at 0°C. Then, the reaction was stirred at 0 to 25°C for 8 hours. The mixture was poured into a saturated aqueous sodium bicarbonate solution and extracted with ethyl acetate. Then, the organic layers were washed with brine, dried with sodium sulfate), filtered and concentrated. The crude product was purified by flash chromatography to provide the title compound (3.2 g, crude) as a yellow solid. 1H NMR (CDCl3, 400 MHz): δ [ppm] = 8.07 (d, 2H), 7.54 (d, 2H), 6.76 (dd, 1H), 5.88 (d, 1H), 5.40 (d, 1H).

1.1.4 SYNTHESIS OF 3-[4-(1-CYCLOPROPYLSULFONYLAZIRIDIN-2-YL)PHENYL]-5- (T RIFLUOROMETHYL)-1,2,4-OXADIAZOLA (EX-4)

[00230] To a solution of 5-(trifluoromethyl)-3-(4-vinylphenyl)-1,2,4-oxadiazole (2.0 g, 8.7 mmol) in acetonitrile (50 mL) cyclopropanesulfonamide (2 .3 g, 19.2 mmol), (diacetoxyiodo)benzene (3.1 g, 9.6 mmol) and tetrakis(acetonitrile)copper(I) (326 mg, 0.87 mmol). Then, the reaction was stirred at 60°C for 16 hours. The mixture was concentrated and purified by flash chromatography to provide the title compound (710 mg, 22.7%) as a yellow solid. 1H NMR (CDCl3, 400 MHz): δ [ppm] = 8.14 (d, 2H), 7.52 (d, 2H), 3.76 (dd, 1H), 3.01 (d, 1H), 2.68 (tt, 1H), 2.48 (d, 1H), 1.42 - 1.26 (m, 2H), 1.20 -1.07 (m, 2H).

1.2 COMPOUNDS OF FORMULA EX-11 TO EX-14 CAN BE PREPARED ACCORDING TO THE METHODS DESCRIBED BELOW 1.2.1 SYNTHESIS OF 3-[4-(OXIRAN-2-YL)PHENYL]-5-(TRIFLUOROMETHYL)-1,2,4-OXADIAZOLE

[00231] To a solution of 5-(trifluoromethyl)-3-(4-vinylphenyl)-1,2,4-oxadiazole (45.0 g, 187.5 mmol) in dichloromethane (1.5 L) acid was added meta-chloroperoxybenzoic acid (85% purity, 76.1 g, 375 mmol) in portions at 25°C. Then, the reaction was stirred at 25°C for 16 hours. The mixture was concentrated to remove approximately 60% dichloromethane and filtered. Then, the filtration was washed with saturated aqueous sodium bicarbonate solutions. The organic phase was dried over sodium sulfate and concentrated, and purified by flash chromatography to provide the title compound (40.0 g, 83.3%) as a yellow solid. 1H NMR (CDCl3, 400 MHz): δ [ppm] = 8.16 - 8.03 (m, 2H), 7.49 - 7.40 (m, 2H), 3.93 (dd, 1H), 3 .21 (dd, 1H), 2.82 (dd, 1H).

1.2.2 SYNTHESIS OF 2-AZIDO-1-[4-[5-(TRIFLUOROMETHYL)-1,2,4-OXADIAZOLE-3- ILPHENYLIETHANOL AND 2-AZIDO-2-[4-[5-(TRIFLUOROMETHYL)-1 ,2,4-OXADIAZOLE-3- ILPHENYLYETHANOL

[00232] For a solution of 3-[4-(oxiran-2-yl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole (20.0 g, 78.1 mmol) in methanol (500 mL) sodium azide (12.7 g, 195.2 mmol) in water (80 mL) was added, then followed by ammonium chloride (234.2 g, 12.5 mmol) in water (80 mL). Then, the reaction was stirred at 25°C for 16 hours. The mixture was concentrated by removing 60% of the methanol and then the organic phase was extracted with ethyl acetate. The organic layers were dried over sodium sulfate, filtered and concentrated. The crude product was purified by flash chromatography to provide 2-azido-1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]ethanol (3.5 g, 15.0 %) as yellow oil and 2-azido-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]ethanol (10.0 g, 42.8%) as solid yellow. 1H NMR (CDCl3 400 MHz): δ [ppm] = 8.13 (d, 2H), 7.61 - 7.50 (m, 2H), 5.01 - 4.92 (m, 1H), 3, 51 (d, 2H), 2.79 - 2.71 (m, 1H). 1H NMR (CDCl3, 400 MHz): δ [ppm] = 8.21-8.14 (m,2H), 7.52 (d, 2H), 4.77 (dd, 1H), 3.87-3 .75 (m, 2H).

1.2.3 SYNTHESIS OF 3-[4-(AZIRIDIN-2-YL)PHENYL|-5-(TRIFLUOROMETHYL)-1,2,4- OXADIAZOLE

[00233] For a solution of 2-azido-1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]ethanol (10.0 g, 33.42 mmol) in Acetonitrile (300 mL) was added triphenylphosphine (17.5 g, 66.8 mmol) in portions at 25°C. Then, the reaction mixture was stirred at 80°C for 8 hours. For a solution of 2-azido-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]ethanol (7.0 g, 23.4 mmol) in acetonitrile (200 mL) triphenylphosphine (12.3 g, 46.8 mmol) was added in portions at 25°C. Then, the reaction was stirred at 80°C for 8 hours. These two reactions were combined and concentrated to remove acetonitrile, the residue was washed with n-hexane. Then, the organic layers were concentrated and purified by flash chromatography to provide the title compound as yellow oil (5.0 g, 34.5%). 1H NMR (CDCl3, 400 MHz): δ [ppm] = 8.07 (d, 2H), 7.41 (d, 2H), 3.12 (s, 1H), 2.42 - 2.21 (m , 1H), 1.78 (br s, 1H).

1.2.4 SYNTHESIS OF N-METHYL-2-[4-[5-(TRIFLUOROMETHYL)-1,2,4-OXADIAZOL-3- IL]PHENYL]AZIRIDINE-1-CARBOXAMIDE (EX-13)

[00234] For a solution of 3-[4-(aziridin-2-yl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole (300 mg, 1.18 mmol) in tetrahydrofuran (5 mL) triethylamine (238 mg, 2.35 mmol) was added at 0°C. Then, acetyl chloride (133 mg, 1.42 mmol) was added to the mixture at 0°C. Then, the reaction was stirred at room temperature for 30 minutes. The reaction was poured into a saturated aqueous solution of sodium bicarbonate and extracted with ethyl acetate, dried over sodium sulfate, filtered and concentrated. Then, the mixture was purified by flash chromatography to provide the title compound as a yellow solid (250 mg, 71.3%). 1H NMR (CDCl3, 400 MHz): δ [ppm] = 8.11 (d, 2H), 7.48 (d, 2H), 3.54 (dd, 1H), 2.80 (d, 1H), 2.31 (d, 1H), 2.25 - 2.17 (m, 3H).

1.3 COMPOUNDS OF FORMULA EX-11 TO EX-30 CAN BE PREPARED ACCORDING TO THE METHODS DESCRIBED BELOW I.3.1 SYNTHESIS OF TERC-BUTYL 3-(4-AMINOPHENYL)AZETIDINE-1-CARBOXYLATE

[00235] Zinc powder (11.1 g, 0.17 mol) and 1,2-dibromoethane (2.9 g, 15.7 mmol) in tetrahydrofuran (100 mL) were stirred at 65°C under atmospheric of nitrogen (15 psi) for 30 minutes and allowed to cool to 25°C while stirring. Trimethylsilyl chloride (1.6 g, 14.4 mmol) was then added and the mixture was stirred at 25°C for 1 hour. A solution of tert-butyl-3-iodoazetidine-1-carboxylate (37.0 g, 0.13 mol) in tetrahydrofuran (100 mL) was then slowly dripped into the reaction mixture and allowed to stir. at 25°C under nitrogen atmosphere (15 psi) for two hours. Another suspension of tris(dibenzylideneacetone dipalladium(0) (1.2 g, 1.3 mmol) and tri(2-furyl)phosphine (1.2 g, 5.2 mmol) in tetrahydrofuran (50 mL) were stirred at 25°C under nitrogen atmosphere (15 psi) for 30 minutes, the prepared organozinc reagent solution was added, then 4-iodobenzonitrile (30.0 g, 0.13 mol) in tetrahydrofuran (150 mL) The resulting mixture was stirred at 65°C for 13 hours. The reaction mixture was filtered through a pad of Celite and the filter cake was washed with methyl tert-butyl ether. The filtrate was washed with saturated aqueous bicarbonate solutions. sodium sulfate and brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography to give the title compound as a yellow solid (12.7 g, 37.7%). , 400 MHz): δ [ppm] = 7.65 (d, 2 H) 7.43 (d, 2 H) 4.37 (t, 2 H) 3.95 (dd, 2 H) 3.72 - 3.83 (m, 1 H) 1.47 (s, 9 H).

1.3.2 SYNTHESIS OF TERC-BUTYL 3-[4-[(Z)-C,N-DI-HYDROXICARBONIMIDOYL]PHENYL]AZETIDINE-1-CARBOXYLATE

[00236] A solution of tert-butyl 3-(4-aminophenyl)azetidine-1-carboxylate (9.9 g, 38.4 mmol) and hydroxylamine hydrochloride (50% aqueous solution, 5.3 g, 76.8 mmol ) in ethanol (150 mL) was stirred at 80°C for 4 hours. Another reaction of tert-butyl 3-(4-aminophenyl)azetidine-1-carboxylate (3 g, 11.6 mmol) reacted in the same way. The reaction mixtures were then combined and worked together. Mixed solution was concentrated in vacuum to remove the solvent. The residue was washed with a solvent mixture of methyl tert-butyl ether (40 ml) and petroleum ether (160 ml) and filtered. The filter cake was washed with water and filtered. The filter cake was dried under vacuum to give the title compound as a white solid (10.7 g, 73.5%). 1H NMR (DMSO-d6, 400 MHz): δ [ppm] = 9.60 (s, 1 H), 7.65 (d, 2 H), 7.33 (d, 2 H), 5.78 ( s, 2 H), 4.24 (br s, 2 H), 3.81 (br s, 3 H), 1.40 (s, 9 H).

1.3.3 SYNTHESIS OF TERC-BUTYL 3-[4-[5-(TRIFLUOROMETHYL)-1,2,4-OXADIAZOL-3- IL]PHENYL]AZETIDINE-1 -CARBOXYLATE

[00237] For a solution of tert-butyl 3-[4-[(Z)-C,N-dihydroxycarbonimidoyl]phenyl]azetidine-1-carboxylate (8.7 g, 29.9 mmol) in N,N - dimethylacetamide (80 mL) trifluoroacetic anhydride (31.4 g, 149.5 mmol) was added at 0°C. The mixture was stirred at 0 to 25°C for 5 hours. The reaction solution was poured into ice water and extracted with ethyl acetate. The organic phase was washed with water, saturated aqueous sodium bicarbonate solutions and brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography to give the title compound as a yellow solid (9.2 g, 83.0%). 1H NMR (CDCl3, 400 MHz): δ [ppm] = 8.04 - 8.17 (m, 2 H), 7.48 (d, 2 H), 4.39 (t, 2 H), 4, 01 (dd, 2 H), 3.74 - 3.87 (m, 1 H), 1.41-1.52 (m, 9 H).

1.3.4 SYNTHESIS OF 3-[4-(AZETIDIN-3-YL)PHENYL]-5-(TRIFLUOROMETHYL)- 1,2,4-OXADIAZOLE HYCLORIDATE

[00238] For a solution of tert-butyl 3-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]azetidine-1-carboxylate (3 g, 8.0 mmol) in ethyl acetate (15 mL) hydrochloric acid in ethyl acetate (4M, 15 mL) was added, and the mixture was stirred at 25 ° C for 5.5 hours. The mixture was concentrated under reduced pressure to give the title compound as a white solid which was used without purification (2.4 g of crude Hcl salt). 1H NMR (DMSO-d6, 400 MHz): δ [ppm] = 8.06-8.11 (m, 2 H) 7.64-7.74 (m, 2 H) 3.92-4.38 ( m, 5 H).

1.3.5 SYNTHESIS OF 1-[3-[4-[5-(TRIFLUOROMETHYL)-1,2,4-OXADIAZOL-3-YL|PHENYL]AZETIDIN- 1 -ILIETENONE (EX-30)

[00239] For a solution of 3-[4-(azetidin-3-yl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole hydrochloride (500 mg, 1.9 mmol) and triethylamine (770 mg, 7.6 mmol) in methylene chloride (10 mL) was added acetyl chloride (180 mg, 2.3 mmol) dropwise at 0°C and the mixture was stirred at 0 to 25°C for 1 hour. The reaction mixture was poured into water and extracted with dichloromethane. The organic phase was washed with water and brine, dried over sodium sulfate and concentrated. The residue was purified by flash chromatography to give the title compound as a white solid (306 mg, 53%). 1H NMR (CDCl3, 400 MHz): δ [ppm] = 8.13 (d, 2 H), 7.48 (d, 2 H), 4.59 (t, 1 H), 4.47 (t, 1 H), 4.19 (dd, 1 H), 4.12 (dd, 1 H), 3.86-3.95 (m, 1 H), 1.95 (s, 3 H).

I.4 COMPOUNDS OF FORMULA EX-31 MAY BE PREPARED ACCORDING TO THE METHODS DESCRIBED BELOW 1.4.1 SYNTHESIS OF TERC -BUTYL 2-(4-CYANOPHENYL)AZETIDINE-1-CARBOXYLATE

[00240] For a mixture of tert-butyl-3-iodoazetidine-1-carboxylate (10.0 g, 35.3 mmol), 4-cyanophenyl)boronic acid (10.4 g, 70.6 mmol), 2- dicyclohexylphosphine-2',6'-dimethoxybiphenyl (2.9 g, 7.06 mmol) and palladium(II) acetate (0.79 g, 3.53 mmol) in acetonitrile (90 mL), a solution of potassium phosphate (22.5 g, 106 mmol) in water (60 mL). Then, the resulting mixture was stirred at 100°C under a nitrogen atmosphere (15 psi) for 13 hours. The mixture was filtered through a pad of Celite and the filter cake was washed with ethyl acetate. The filtrate was partitioned and the organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography to give the title compound as a yellow solid. (5.1 g, 57.3%). 1H NMR (CDCl3, 400 MHz): δ [ppm] = 7.65 (d, 2 H), 7.46 (d, 2 H), 5.23 (t, 1 H), 3.92-4, 07 (m, 2 H), 2.60-2.71 (m, 1 H), 2.06-2.14 (m, 1 H), 1.29 - 1.48 (m, 9 H).

1.4.2 SYNTHESIS OF TERC-BUTYL 2-[4-[(Z)-N’- HYDROXICARBAMIMIDOYL]PHENYL]AZETIDINE-1-CARBOXYLATE

[00241] A solution of tert-butyl 2-(4-cyanophenyl)azetidine-1-carboxylate (3.6 g, 14.0 mmol) and hydroxylamine (HCl salt, 1.9 g, 28.0 mmol) and triethylamine (4.4 g, 42.0 mmol) in ethanol (40 mL) was stirred at 80°C for 4 hours. The reaction mixture was concentrated under reduced pressure. The residue was washed with a solvent mixture of tert-butyl methyl ether and petroleum ether and filtered. The filter cake was washed with water and filtered. The filter cake was dried under vacuum to give the title compound as a white solid (2.8 g, 69%). 1H NMR (DMSO-d6, 400 MHz): δ [ppm] = 9.61 (s, 1 H), 7.66 (d, 2 H), 7.34 (d, 2 H), 5.80 ( s, 2 H), 5.14 (dd, 1 H), 3.90 (t, 2 H), 2.58 - 2.65 (m, 1 H), 2.02 (s, 1 H), 1.15 - 1.45 (m, 9 H).

1.4.3 SYNTHESIS OF TERC-BUTYL 2-[4-[5-(TRIFLUOROMETHYL)-1,2,4-OXADIAZOL-3- IL]PHENYL]AZETIDINE-1-CARBOXYLATE

[00242] For a solution of tert-butyl 2-[4-[(Z)-N'-hydroxycarbamimidoyl]phenyl]azetidine-1-carboxylate (1.8 g, 6.2 mmol) and triethylamine (1.3 g , 12.4 mmol) in N,N-dimethylacetamide (20 mL) trifluoroacetic anhydride (6.5 g, 31.0 mmol) was added at 0°C. The mixture was stirred at 0 to 25°C for 8 hours. The reaction solution was poured into ice water and extracted with methyl tert-butyl ether. The organic phase was washed with water and brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography to give the title compound as a yellow solid (0.84 g, 37%). 1H NMR (CDCl3, 400 MHz): δ [ppm] = 8.12 (d, 2 H), 7.52 (d, 2 H), 5.27 (br t, 1 H), 3.98 - 4 .08 (m, 2 H), 2.62 - 2.72 (m, 1 H), 2.09 - 2.22 (m, 1 H), 1.21 - 1.46 (m, 9 H) .

1.4.4 SYNTHESIS OF 1 -[2-[4-[5-(TRIFLUOROMETHYL)-1,2,4-OXADIAZOL-3- IL]PHENYL]AZETIDIN-1 -ILIETENONE (EX-31)

[00243] A mixture of tert-butyl 2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]azetidine-1-carboxylate (600 mg, 1.6 mmol) and 2,6-lutidine (1.0 g, 9.8 mmol) in methylene chloride (10 mL) was cooled to 0°C, then trimethylsilyl trifluoromethanesulfonate (1.4 g, 6.5 mmol) was added by dripping, and the resulting mixture was stirred at 25°C for 4 hours. The reaction was cooled to 0°C again, and acetyl chloride (156 mg, 2.0 mmol) was added at 0°C. The reaction was stirred at 0°C for 0.5 hour. The reaction mixture was poured into water and extracted with methylene chloride. The organic phase was washed with water and brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography to give the title compound as a yellow solid (149 mg, 29%). 1H NMR (CDCl3, 400 MHz): δ [ppm] = 8.03 - 8.23 (m, 2 H), 7.42 - 7.59 (m, 2 H), 5.35 - 5.48 ( m, 1 H), 4.07 - 4.31 (m, 2 H), 2.71 - 2.86 (m, 1 H), 2.11 - 2.25 (m, 1 H), 1, 65 - 2.02 (m, 3 H).

[00244] The compounds listed in Table C.1, C.2 and C.3 were prepared in an analogous manner.

TABLE C.1

[00245] Compounds Ex-1 to Ex-14 of formula IH, in which the meaning of L and R1 are as defined in each line.

TABLE C.2

[00246] Compounds Ex-15 to Ex-30 of formula IF, in which the meaning of L and R1 are as defined in each line.

TABLE C.3

[00247] Compounds Ex-31 of formula IG, in which the meaning of L and R1 are as defined. * HPLC: High Performance Liquid Chromatography (HPLC); Kinetex XB C18 HPLC column 1.7μ (50 x 2.1 mm); eluent: acetonitrile / water + 0.1% trifluoroacetic acid (gradient from 5:95 to 100:0 in 1.5 min at 60°C, flow gradient from 0.8 to 1.0 mL/min and, 1, 5 min). MS: Four-Pole Electrospray Ionization, 80 V (positive mode). Rt: retention time in minutes.

II. BIOLOGICAL EXAMPLES FOR FUNGICIDAL ACTIVITY

[00248] The fungicidal action of compounds of formula I was demonstrated by the following experiments:

A. GREENHOUSE TESTS

[00249] The spray solutions were prepared in several steps: The stock solution was prepared: a mixture of acetone and/or dimethylsulfoxide and Wettol wetting/emulsifying agent, which is based on ethoxylated alkylphenols, in a solvent ratio (by volume) for 99 to 1 emulsifier, 25 mg of the compound was added to give a total of 5 mL. Water was then added to the total volume of 100 mL. This stock solution was diluted with the described solvent-emulsifier-water mixture to the given concentration.

TO 1. CURATIVE CONTROL OF SOYBEAN RUST IN SOYBEAN CAUSED BY PHAKOPSORA PACHYRHIZI

[00250] Leaves of soybean seedlings grown in pots were inoculated with Phakopsora pachyrhizi spores. To ensure the success of artificial inoculation, plants were transferred to a humid chamber with a relative humidity of about 95% and 20 to 24°C for 24 hours. The next day, plants were grown for 3 days in a greenhouse chamber at 23 to 27°C and a relative humidity between 60 and 80%. Then, the plants were sprayed until runoff with an aqueous suspension, containing the concentration of active ingredient or its mixture as described below. The plants were allowed to air dry. Then, the test plants were grown for 14 days in a greenhouse chamber at 23 to 27°C and a relative humidity between 60 and 80%. The degree of fungal attack on the leaves was visually evaluated as % of infected leaf area.

[00251] In this test, plants that had been treated with 16 ppm of the active compounds Ex-11, Ex-13, Ex-16, Ex-17, Ex-18, Ex-21, Ex-22, Ex-26, Ex-27, Ex-28, Ex-29, Ex-30 and Ex-31 showed an infected leaf area of a maximum of 18%, while untreated plants showed 100% infected leaf area.

[00252] In this test, plants that had been treated with 63 ppm of the active compounds Ex-6, Ex-7, Ex-8, Ex-9, Ex-11, Ex-12, Ex-14 and Ex-20 showed an infected leaf area of a maximum of 4%, while untreated plants had 100% infected leaf area.

A.2. PROTECTIVE CONTROL OF SOYBEAN RUST IN SOYBEAN CAUSED BY PHAKOPSORA PACHYRHIZI

[00253] Leaves of soybean seedlings grown in pots were sprayed until runoff with an aqueous suspension containing the concentration of active ingredient or its mixture as described below. The plants were allowed to air dry. Test plants were grown for 2 days in a greenhouse chamber at 23 to 27°C and a relative humidity between 60 and 80%. Then, the plants were inoculated with Phakopsora pachyrhizi spores. To ensure the success of artificial inoculation, plants were transferred to a humid chamber with a relative humidity of about 95% and 20 to 24°C for 24 hours. The test plants were grown for fourteen days in a greenhouse chamber at 23 to 27°C and a relative humidity between 60 and 80%. The degree of fungal attack on the leaves was visually evaluated as % of infected leaf area.

[00254] In this test, plants that had been treated with 16 ppm of the active compounds Ex-15, Ex-16, Ex-17, Ex-18, Ex-19, Ex-21, Ex-22, Ex-23, Ex-26, Ex-27, Ex-28, Ex-29, Ex-30 and Ex-31 showed an infected leaf area of at most 8%, while untreated plants showed 100% infected leaf area.

[00255] In this test, plants that had been treated with 16 ppm of the active compounds Ex-9, Ex-11, Ex-12 and Ex-14 showed an infected leaf area of at most 9%, while untreated plants showed 80% of infected leaf area.

[00256] In this test, plants that had been treated with 63 ppm of the active compounds Ex-2, Ex-3, Ex-5, Ex-6, Ex-7, Ex-8 and Ex-20 showed an infected leaf area of a maximum of 17%, while untreated plants had 80% of infected leaf area.

3. CURATIVE CONTROL OF WHEAT LEAF RUST CAUSED BY PUCCINIA RECONDITA

[00257] The first two developed leaves of wheat seedlings grown in pots were sprinkled with spores of Puccinia recondita. To ensure the success of artificial inoculation, plants were transferred to a light-free humid chamber with a relative humidity of about 95 to 99% and 20 to 24°C for 24 hours. The next day, plants were grown for 3 days in a greenhouse chamber at 20 to 24°C and a relative humidity between 65 and 70%. Then, the plants were sprayed until runoff with an aqueous suspension, containing the concentration of active ingredient or its mixture as described below. The plants could be air-dried. Then, the test plants were grown for 8 days in a greenhouse chamber at 20 to 24°C and a relative humidity between 65 and 70%. The degree of fungal attack on the leaves was visually evaluated as % of infected leaf area.

[00258] In this test, plants that had been treated with 63 ppm of the active compounds Ex-15, Ex-17, Ex-18, Ex-19, Ex-21, Ex-22, Ex-23, Ex-26, Ex-27, Ex-28, Ex-29, Ex-30 and Ex-31 showed an infected leaf area of at most 8%, while untreated plants showed 90% infected leaf area.

4. PREVENTIVE CONTROL OF WHEAT LEAF RUST CAUSED BY PUCCINIA RECONDITA

[00259] The first two developed leaves of wheat seedlings grown in pots were sprayed until runoff with an aqueous suspension containing the concentration of active ingredient or mixture thereof as described below. The following day, the plants were inoculated with Puccinia recondita spores. To ensure the success of artificial inoculation, plants were transferred to a light-free humid chamber with a relative humidity of about 95 to 99% and 20 to 24°C for 24 hours. Then, the test plants were grown for 6 days in a greenhouse chamber at 20 to 24°C and a relative humidity between 65 and 70%. The degree of fungal attack on the leaves was visually evaluated as % of infected leaf area.

[00260] In this test, plants that had been treated with 63 ppm of the active compounds Ex-16, Ex-17, Ex-18, Ex-19, Ex-21, Ex-23, Ex-26, Ex-27, Ex-28, Ex-29 and Ex-30 showed an infected leaf area of a maximum of 12%, while untreated plants showed 90% infected leaf area.

[00261] In this test, plants that had been treated with 63 ppm of the active compounds Ex-2, Ex-4, Ex-5, Ex-6, Ex-7, Ex-8 and Ex-20 showed an infected leaf area of a maximum of 17%, while untreated plants had 80% of infected leaf area.

Claims (16)

1. COMPOUNDS of formula I, or N-oxides, or agriculturally acceptable salts thereof, characterized by the fact that: A is phenyl or a 5- or 6-membered aromatic heterocycle; wherein the ring member atoms of the aromatic heterocycle include, in addition to carbon atoms, 1, 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms with the proviso that the heterocycle cannot contain 2 contiguous atoms selected from O and S; and wherein the phenyl ring or aromatic heterocycle is unsubstituted or substituted by 1, 2, 3 or 4 identical or different RA groups; where RA is halogen, cyano, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy or C1-C6 haloalkoxy; W is a 3- or 4-membered non-aromatic heterocycle that contains as ring member atoms, in addition to carbon atoms, 1 nitrogen atom; wherein the heterocycle is attached to the L group through said ring member nitrogen atom; and wherein the heterocycle is linked to group A through one of the ring member carbon atoms; and wherein the heterocycle is further unsubstituted or substituted by 1, 2, 3 or 4 identical or different RW radicals; wherein RW is halogen, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy or C1-C3 haloalkoxy; L is -C(=O)-, -C(=S)-, -S(=O)p-, -C(=O)-O-#, -C(=O)NR2-# or - C (=S)NR2-#; where # denotes the position, in which it is linked to the radical R1; and where p is 0, 1 or 2; R2 is hydrogen, formyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C5 cycloalkyl, C1-C6 alkoxy or C1-C6 haloalkyl; R1 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C3-C6 alkynyl, C1-C6-alkoxyimino-C1-C4-alkyl, C2-C6-alkenyloxyimino-C1-C4-alkyl, C2-C6-alkynyloxyimino-C1 -C4-alkyl, C3-C11 cycloalkyl, C3-C11 cycloalkenyl, C3-C11-cycloalkyl-C1-C4-alkyl, phenyl-C1-C4-alkyl, heterocyclyl-C1-C4-alkyl, heteroaryl-C1-C4-alkyl , phenyl, naphthyl or a mono- or bicyclic, saturated, partially unsaturated or aromatic heterocycle of 3 to 10 members, wherein the ring member atoms of said mono- or bicyclic heterocycle include, in addition to carbon atoms, a further 1, 2 , 3 or 4 heteroatoms selected from N, O and S as ring member atoms with the proviso that the heterocycle cannot contain 2 contiguous atoms selected from O and S; and wherein 1 or 2 member atoms of the carbon ring of the heterocycle may be replaced by 1 or 2 groups, independently selected from C(=O) and C(=S); and wherein the heterocyclyl group in heterocyclyl-C1-C4-alkyl is a saturated, partially unsaturated, 3- to 10-membered mono- or bicyclic heterocycle, wherein the ring member atoms of said mono- or bicyclic heterocycle include in addition of carbon atoms, plus 1, 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms, with the proviso that the heterocycle cannot contain 2 contiguous atoms selected from O and S; and wherein 1 or 2 member atoms of the carbon ring of the heterocycle may be replaced by 1 or 2 groups, independently selected from C(=O) and C(=S); and wherein the heteroaryl group in heteroaryl-C1-C4-alkyl is a 5- or 6-membered aromatic heterocycle, wherein the ring member atoms of the aromatic heterocycle include, in addition to carbon atoms, 1, 2, 3 or 4 selected heteroatoms from N, O and S as ring member atoms with the proviso that the heterocycle cannot contain 2 contiguous atoms selected from O and S; and wherein any of the aliphatic or cyclic R1 groups are unsubstituted or substituted by 1, 2, 3 or up to the maximum possible number of identical or different R1a groups; where R1a is halogen, cyano, C1-C6 alkyl, C1-C6 alkoxy or C1-C6 haloalkoxy. 2. COMPOUNDS, according to claim 1, characterized by the fact that A in the compounds of formula I is phenyl. 3. COMPOUNDS, according to claim 2, characterized by the fact that they are of formula I.1, or the N-oxides, or the agriculturally acceptable salts thereof, wherein n is 0, 1 or 2, and wherein the meaning of the variables RA, W, L, R1 and R2, is as defined in claim 1 for compounds of formula I. 4. COMPOUNDS according to any one of claims 1 to 3, characterized in that W is selected from the group consisting of Wa, Wb and Wc, where # denotes the position, in which it is fixed to group A, and the dashed line denotes the position, in which it is fixed to R1. 5. COMPOUNDS, according to any one of claims 1 to 4, characterized by the fact that L is -C(=O)-. 6. COMPOUNDS, according to any one of claims 1 to 4, characterized by the fact that L is -S(=O)2-. 7. COMPOUNDS, according to any one of claims 1 to 4, characterized by the fact that L is -C(=O)NR2-# or -C(=S)NR2-#; where # denotes the position, in which it is linked to the radical R1. 8. COMPOUNDS according to any one of claims 1 to 7, characterized by the fact that R1 is hydrogen, C1C6 alkyl, C2-C6 alkenyl, C3-C6 alkynyl or C3-C11 cycloalkyl. 9. COMPOUNDS according to any one of claims 1 to 7, characterized by the fact that R1 is hydrogen, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert- butyl or cyclopropyl. 10. INTERMEDIATE COMPOUNDS, of formula II characterized by the fact that the variables A, RA, W and RW are as defined in claim 1 for compounds of formula i. 11. INTERMEDIATE COMPOUNDS, of formula XV characterized by the fact that the variables A, RA, W, RW, L, p, R1 and R2 are as defined in claim 1 for compounds of formula i. 12. AGROCHEMICAL COMPOSITION, characterized by the fact that it comprises an auxiliary and at least one compound, as defined in any one of claims 1 to 9. 13. COMPOSITION, according to claim 12, characterized by the fact that it further comprises seed, wherein the amount of at least one compound is 0.1 g to 10 kg per 100 kg of seed. 14. USE OF COMPOUNDS, as defined in any one of claims 1 to 9, characterized by the fact that it is to combat harmful phytopathogenic fungi, with the exception of use for the therapeutic treatment of the human or animal body. 15. METHOD FOR COMBATING HARMFUL PHYTOPATHOGENIC FUNGI, characterized by the fact that the process comprises treating the plants, soil or seeds to be protected against fungal attack, with an effective quantity of at least one compound, as defined in any of the claims 1 to 9. 16. COATED SEED, characterized by the fact that it is coated with the composition as defined in any one of claims 12 to 13.