DE4440121A1 - Synergistic herbicide combinations for use in rice crops - Google Patents

Abstract

A herbicide contains (A) a substd. N-phenoxysulphonyl-N'-(4,6-disubstd. pyrimid-2-yl)urea deriv. of formula (I) or its salt; and (B) a (2-fluoro-4-cyanophenoxy)phenoxypropionic acid ester of formula (II) or its salt. In (I), either (a) R<1> = OEt, OPr or O-i-Pr; R<2> = halogen, NO2, CF3, CN, 1-4C alkyl, 1-4C alkoxy, 1-4C alkylthio or (1-4C alkoxy)carbonyl; and n = 0-3; or (b) R<1> = halogen, OMe, Et or Pr; R<2> = (1-4C alkoxy) carbonyl in position 6 on the Ph ring; and n = 1: R<3> = H, opt. satd. 1-8C alkyl or 1-4C alkoxy; R<4>, R<5> = H, halogen, 1-4C alkyl, 1-4C alkoxy, 1-4C alkylthio (these 3 opt. substd. with halogen, 1-4C alkoxy or 1-4C alkylthio); Y = O or S; E = CH or N; R<6> = H or 1-6C alkyl.

Description

The invention is in the field of crop protection agents against monocotyledons and dicotyledon weeds can be used. In the German Patent applications P 38 16 704.2 (EP-A-0 342 569), P 38 16 703.4 (EP-A-0 342 568) and P 39 09 053.1 (EP-A-0 388 771) are heterocyclically substituted Phenoxysulfonylurea described with which a wide range of mono- and dicotyledon weeds can be controlled. You can use it both as a soil herbicide as well as over the sheet and also show a particularly high Selectivity in monocot crops such as cereals, corn and rice.

P 39 33 543.7 and P 40 31 799.4 and P 42 09 475.5 are mixtures of active substances known to counter a synergistic increase in control success important problem weeds in cereals and rice.

However, there are a number of very important monocotyledons in rice Weeds, such as B. Cyperus serotinus, Sagittaria spp., Eleocharis spp., Scirpus spp., Echinochloa spp. u. a. those with the mixtures mentioned alone are not in are to be fought optimally.

Surprisingly, herbicidal active ingredients have now been found in biological tests identified when used in conjunction with the above Individual compounds markedly synergistic properties with regard to the Have effectiveness against weeds and thus from P 39 33 543.7 and P 42 09 475.5 known combinations are superior.  

The present invention relates to herbicidal compositions, characterized by an effective content of

• A) Compounds of the general formula (I) or their salts wherein
  a₁) R¹ ethoxy, propoxy or isopropoxy and
  R² halogen, NO₂, CF₃, CN, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-
  C₄-alkylthio or (C₁-C₄-alkoxy) carbonyl and n 0, 1, 2 or 3 or
  a₂) R¹ each in the 2-position on the phenyl radical - halogen, methoxy, ethyl or propyl,
  R² (C₁-C₄ alkoxy) carbonyl in 6-position in the phenyl radical and
  n = 1
  and in all cases a₁) and a₂)
  R³ is hydrogen, saturated or unsaturated C₁-C₈-alkyl or C₁-C₄-alkoxy,
  R⁴, R⁵ independently of one another hydrogen, halogen, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio, the latter three radicals being unsubstituted or substituted by halogen, C₁-C₄-alkoxy or C₁-C₄-alkylthio ,
  YO or S and
  E CH or N
  mean,
  in combination with the compound of formula II (DEH-112, 2-fluoro-4-cyanaphenoxyphenoxypropionic acid ester, B) or their salts wherein R⁶ is hydrogen or (C₁-C₆) alkyl.

If required, one or more known combination partners can be used as further combination partners Rice herbicides of various structure classes can be used. Of of particular interest are compounds from the class of the sulfonylureas, of ureas, amides, cyclohexanediones, thiocarbamates or Chloroacetanilides.

The following are specific examples of such combination partners Connections mentioned, without any limitation:

C1, AC-014
C2, Anilofos
C3, bentazone
C4, bensulfuron-methyl
C5, benzofenap
C6, bromobutide
C7, butachlor
C8, butenachlor
C9, cinmethylin
C10, cinosulfuron
C11, α-chloro-N- (3-methoxy-2-thienyl) methyl-2 ′, 6′-dimethylacetanilide (NSK-850)
C12, daimuron (1- (1-methyl-1-phenylethyl) -3-p-tolylurea)
C13, 1-diethylcarbamoyl-3- (2,4,6-trimethylphenylsulfonyl-1,2,4-triazole (CH-900)
C14, dimepiperate
C15, dimethametryn
C16, dithiopyr
C17, DPX-47
C18, Esprocarb
C19, 4-ethoxybenz-2 ′, 3′-dihydrochloranilide (HW-52)
C20, fenoxaprop-ethyl or fenoxaprop-P-ethyl
C21, imazosulfuron
C22, JC 940 (1- (2-chlorobenzyl) -3- (α, α-dimethylbenzyl) urea
C23, MCPB
C24, Mefenacet
C25, Molinate
C26, naproanilides
C27, Piperophos
C28, pretilachlor
C29, propanil
C30, pyrazosulfuron-ethyl
C31, pyrazoxyfen
C32, pyrazolates
C33, quinchlorac
C34, Simetryn
C35, Sulcotrione (chloromesulone, ICI-A0051)
C36, thiobencarb
C37, 2,4-D

However, other rice herbicides can also be used together with the invention Combination can be used advantageously.

Compound A is from the German patent applications mentioned at the beginning known. The compound of formula B is from the European patent application EP 0 302 203 became known.  

Stereochemistry was used for the formulas for compounds A and B not specified in detail. If stereoisomers can occur, use the formulas also include all geometric isomers, enantiomers and diastereomers and mixtures thereof.

The compound DPX-47 = DPX-A8947, N - (((4-6-dimethoxypyrimidin-2-yl) amino carboxyl) -1-methyl-4- (2-methyl-2H-tetrazol-5-yl) -1-H-pyrazol-5-sulfo-namide has the following structural formula:

The compound AC-014, 1- (2- (cyclopropylcarbonylphenyl) sulfamoyl) -3- (4,6- dimethoxy-pyrimidin-2-yl) urea has the following structural formula

and is known from U.S. Patent 5,009,699 dated June 22, 1990.

The compound JC 940 is from Japanese patent application J-60087254 known.

The compound imazosulfuron (TH-913) is known from the patent application EP- A-0 238 070 (see example 1).  

The compound NSK-850 (α-chloro-N- (3-methoxy-2-thienyl) -methyl-2 ′, 6′- dimethylacetanilide) is from M. Ogasawara et al. in "Weed Research", (Tokyo), 1989, Pages 131 to 137.

The compound HW-52 (4-ethoxybenz-2,3-dihydrochloranilide) is from N. Ichizen et al. In "Weed Research", (Tokyo), 1990, pages 261 to 267.

The compound CH-900 (1-diethylcarbamoyl-3- (2,4,6-trimethylphenylsulfonyl) -1,2,4- triazole) is described in EP-332 133.

The compound sulcotrione (chloromesulone, 2- (2-chloro-4-mesylbenzoyl) - cyclohexane-1,3-dione) is from EP 0 298 680 (see page 13, compound no. 51A) known. The other type C compounds are in "The Pesticide Manual", British Crop Protection Council, 9th Ed., 1991.

Of particular interest are herbicidal compositions according to the invention with compounds of the formula (I) mentioned or their salts, in which
a₁) R¹ ethoxy, propoxy or isopropoxy and
R² is oriented in position 6 and has the meaning given above, and
n O or 1 or
in all cases a₁) and a₂)
R³, hydrogen, C₁-C₄-alkyl, especially hydrogen or methyl,
R⁴, R⁵ halogen, C₁-C₄-alkyl, C₁-C₄-alkoxy or C₁-C₄-alkylthio, the latter 3 radicals being unsubstituted or substituted by halogen, C₁-C₄-alkoxy or C₁-C₄-alkylthio,
YQ, and
E CH mean.

Saturated or unsaturated alkyl and alkoxy means accordingly  straight-chain or branched alkyl or alkoxy, halogen means F, Cl, Br and J, preferably F and Cl.

The compounds of formula (I) can form salts in which the hydrogen the -SO₂-NH group replaced by a cation suitable for agriculture becomes. These salts are generally metal, especially alkali, alkaline earth, optionally alkylated ammonium or organic amine salts.

Preferred herbicidal compositions comprise one or more as compounds A. Compounds of the formulas A1, A2 and A3, where the formulas mean the following:

Here are specific examples of the active ingredient mixtures claimed mentioned without any restriction:

1. A₁ + B
2. A₁ + B + C10 (NSK 850)
3. A₁ + B + C11 (CH 900)
4. A₁ + B + C25 (pretilachlor)

The combinations according to the invention show a when used together extraordinarily good effectiveness against a broad spectrum economically important mono- and dicotyledonous harmful plants. Even difficult to fight perennial weeds made from rhizomes, rhizomes or others Expelling permanent organs are well captured by the active ingredient combinations. It does not matter whether the substances are pre-seeded, pre-emergence or Post-emergence procedures are applied. Some are examples in detail Representative of the monocotyledonous and dicotyledonous weed flora, caused by the agents according to the invention can be controlled without being mentioned a restriction to certain types should be made.

On the side of the monocot weed species, e.g. B. Echinochloa as well Cyperus species from the annual group and on the part of the perennial species persistent cyperus species well recorded. The under the specific Culture conditions in weeds occurring in rice, such as. B. Sagittaria, Alisma, Rotala, Monochoria, Eleocharis, Scirpus, Cyperus etc. are used by the Combined active ingredient combinations according to the invention excellently.

Are the herbicidal compositions according to the invention before germination on the Applied earth surface, so is either the emergence of the weed seedlings completely prevented, or the weeds grow to the cotyledon stage approach, but then stop growing and eventually die after it expires from three to four weeks.

When applying the active ingredient combinations to the green parts of the plant or in that Irrigation water from the rice culture in the post-emergence process also occurs very much a drastic growth stop rapidly after treatment. The Weed plants remain in the one available at the application tent point Stages of growth stand or die after a certain time more or less  quickly, so that in this way a harmful to the crop Weed competition very early and sustainably through the use of the new agents according to the invention can be eliminated.

Although the compositions according to the invention have excellent herbicidal activity against monocotyledonous and dicotyledonous weeds, the crop is rice only slightly or not at all damaged. The funds are suitable from these Reasons especially in rice very good for selective control of unwanted vegetation.

They are the known herbicides in terms of potency and potency and herbicide combinations are superior and can be applied in small amounts be used. Other advantages of these new combinations are theirs Persistent long-term effect that lasts for several weeks, and consequently subsequent ones Herbicide applications against newly germinating weeds are no longer necessary. So can a second Work step can be saved by using a single application competing weed growth is eliminated.

The active compound combinations according to the invention have a herbicidal action achieved that goes beyond what is due to the effect of Individual components are to be expected. These increases in effectiveness allow the Significantly reduce the amounts of the individual active ingredients. The combination The herbicide can also speed up the rate of action cause. Such properties offer the user considerable advantages practical weed control. He can use weeds cheaper, faster, with Combat less effort and more permanently and thereby in one Crop crops harvest more yield.

It was also found that a number of the active ingredient combinations There is a strong safener or antidote effect, d. H. that phytotoxic Side effects of the active ingredients used in crops, such as. B. the rice, be reduced or avoided altogether.  

The mixing ratios A: B can fluctuate within wide limits and are usually between 1: 1 and 1:40. The choice of the mixing ratio is depending on the mixing partner, stage of development of the weeds, Weed spectrum and climatic conditions.

Mixing ratios for A: B of 1: 5 to 1:30 are preferably used. The application rates of herbicide A in the active compound mixtures are preferred between 10 and 100 g / ha, the application rates of B between 50 and 600 g / ha. The application rates for compounds from group C are because it is partly is about different structure classes, very different and depending on Active ingredient in the range from a few grams up to 3 kg AS / ha.

The active compound combinations according to the invention can be used both as Mixed formulations of the two components are present, which are then more common Way to be applied diluted with water, or as so-called Tank mixes by diluting the separately formulated Components are made with water.

The compounds A and B or their combinations with C can different types, depending on which biological and / or chemical-physical parameters are specified.

Possible formulation options are, for example: wettable powder (WP), water-soluble powder (SP), water-soluble concentrates, emulsifiable Concentrates (EC), aqueous solutions (SL), emulsions (EW) such as oil in water and Water-in-oil emulsions, sprayable solutions or emulsions, dispersions based on oil or water, suspension concentrates (SC), (suspension emulsions), oil-miscible solutions, capsule suspensions (CS), dusts (DP), mordants, Granules for soil or litter application, granules (GR) in the form of micro, Spray, elevator and adsorption granules, water-soluble granules (SG), water-dispersible granules (WG), ULV formulations, microcapsules or Waxes.  

These individual types of formulation are known in principle and will described for example in: Winnacker-Küchler, "Chemical Technology", volume 7, C. Hauser Verlag Munich, 4th ed. 1986; van Valkenburg, "Pesticide Formulations ", Marcel Dekker H. Y., 2nd Ed. 1972-73; K. Martens," Spray Drying Handbook ", 3rd Ed. 1979, G. Goodwin Ltd. London.

The necessary formulation aids such as inert materials, surfactants, Solvents and other additives are also known and will be described for example in: Watkins, "Handbook of Insecticide Dust Diluents and Carriers ", 2nd Ed., Darland Books, Caldwell N.J .; H. v. Olphen," Introduction to Clay Colloid Chemistry ", 2nd Ed., J. Wiley Sons, N.Y., Marsden," Solvents Guide ", 2nd Ed., Interscience, N.Y. 1950; McCutcheon's, "Detergents and Emulsifiers Annual ", MG Publ. Gorp., Ridgewood N.J .; Sisley and Wood," Encyclopedia of Surface Active Agents ", Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt, Interface-active ethylene oxide adducts ", Wiss. Verlagsgesellschaft., Stuttgart 1976; Winnacker-Küchler, "Chemical Technology", Volume 7, G. Hauser Verlag Munich, 4th ed. 1986.

Based on these formulations, combinations with others can also be made pesticidal substances, such as other herbicides, fungicides or insecticides, as well as producing fertilizers and / or growth regulators, e.g. B. in the form of a Ready formulation or as a tank mix.

Spray powders are preparations which are uniformly dispersible in water Active substance in addition to a diluent or an inert substance or ionic surfactants and / or nonionic type (wetting agents, dispersing agents), e.g. B. polyoxethylated Alkylphenols, polyoxethylated fatty alcohols or fatty amines, Fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, sodium lignosulfonate, 2,2′-dinaphthylmethane-6,6′-disulfonic acid sodium, dibutylnaphthalene-sulfonic acid sodium or oleoylmethyltauric acid sodium contain. The herbicidal active ingredients are used to produce the wettable powders for example in conventional fittings such as hammer mills, fan mills or  Air jet mills finely ground and simultaneously or subsequently with the Formulation aids mixed.

Emulsifiable concentrates are made by dissolving the active ingredient in one organic solvents, e.g. B. butanol, cyclohexanone, dimethylformamide, xylene or also higher-boiling aromatics or hydrocarbons or mixtures the organic solvent with the addition of one or more surfactants ionic and / or nonionic type (emulsifiers). As emulsifiers can be used for example: alkylarylsulfonic acid calcium salts such as Ca-dodecylbenzenesulfonate or nonionic emulsifiers such as Fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, Propylene oxide-ethylene oxide condensation products, alkyl polyethers, Sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters or Polyoxethylene sorbitol ester.

Dusts are obtained by grinding the active ingredient with finely divided solid Fabrics, e.g. B. talc, natural clays such as kaolin, bentonite and pyrophyllite or Diatomaceous earth.

Suspension concentrates can be water or oil based. You can for example by wet grinding using commercially available pearl mills and optionally addition of surfactants, such as. B. above with the others Formulation types already listed can be produced.

Emulsions e.g. B. oil-in-water emulsions (EW) can be used, for example Stirrers, colloid mills and / or static mixers using aqueous organic solvents and optionally surfactants such as z. B. already listed above for the other formulation types.

Granules can either by spraying the active ingredient adsorbable, granulated inert material or by Applying active ingredient concentrates using adhesives, e.g. B. polyvinyl alcohol,  polyacrylic acid sodium or mineral oils, on the surface of Carriers such as sand, kaolinites or granulated inert material. Can too suitable active ingredients in the usual for the production of fertilizer granules Way - if desired in a mixture with fertilizers - granulated.

Water-dispersible granules are generally made using the customary methods such as spray drying, fluidized bed granulation, plate granulation, mixing with High speed mixers and extrusion made without solid inert material.

The agrochemical preparations usually contain 0.1 to 99 Percentages by weight, in particular 2 to 95% by weight, of active ingredients A and B and optionally C. The concentrations of active ingredients A, B and C can be in the Formulations may be different.

In wettable powders, the active ingredient concentration is e.g. B. about 10 to 95 wt .-% of The remainder to 100 wt .-% consists of conventional formulation components. At emulsifiable concentrates, the active ingredient concentration can be about 1 to 85% by weight, preferably 5 to 80 wt .-%. Contain dusty formulations about 1 to 25 wt .-%, mostly 5 to 20 wt .-% of active ingredient, sprayable Solutions about 0.2 to 25 wt .-%, preferably 2 to 20 wt .-% active ingredient. At Granules such as water-dispersible granules depend on the active ingredient content Part of whether the active compound is liquid or solid and which Granulation aids and fillers can be used. As a rule, the salary is in the case of the water-dispersible granules between 10 and 90% by weight. At Scatter granules that are sprinkled directly into the irrigation water are in active substance contents of 1 to 10% are generally preferred.

In addition, the active ingredient formulations mentioned optionally contain the usual adhesive, wetting, dispersing, emulsifying, penetration, preservation, Antifreeze and solvents, fillers, carriers and dyes, defoamers, Evaporation inhibitors and agents that affect pH and viscosity.  

The formulations available in commercial form are used optionally diluted in a conventional manner, e.g. B. with wettable powders, emulsifiable Concentrates, dispersions and water-dispersible granules using water. Dust-like preparations, ground or scatter granules, as well as sprayable Solutions are usually no longer combined with other solutions before use inert substances diluted.

With the external conditions such as temperature, humidity, the type of used herbicide u. a. the required application rate varies Compounds A and B. The additional application rate required Rice herbicides used (C) also vary depending on the external Conditions.

The following examples serve to explain the invention:

• A. Examples of formulation
• a) A dusting agent is obtained by adding 10 parts by weight of a Active ingredient combination according to the invention and 90 parts by weight of talc as an inert substance mixes and crushed in a hammer mill.
• b) A wettable powder which is readily dispersible in water is obtained by 25 parts by weight of active ingredient A + B, 64 parts by weight of quartz containing kaolin as Inert substance, 10 parts by weight of potassium lignosulfonate and 1 part by weight oleoylmethyltauric acid sodium as a wetting and dispersing agent and mixed in one Pin mill grinds.
• c) A dispersion concentrate which is easily dispersible in water is obtained by 20 parts by weight of active compound A + B with 6 parts by weight of alkylphenol polyglycol ether (®Triton X 207), 3 parts by weight of isotridecanol polyglycol ether (8 E0) and 71 parts by weight of paraffinic mineral oil (boiling range e.g. approx. 255 to above 277 ° C) mixes and ground in a attritor to a fineness of less than 5 microns.  
• d) An emulsifiable concentrate is obtained from 15 parts by weight of active compound A + B, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of ethoxylated Nonylphenol as an emulsifier.
• e) A water-dispersible granulate is obtained by adding 75 parts by weight of active ingredients A + B,
  10 parts by weight of calcium lignosulfonic acid,
  5 parts by weight of sodium lauryl sulfate,
  3 parts by weight of polyvinyl alcohol and
  7 parts by weight of kaolin mixed, ground on a pin mill and the powder granulated in a fluidized bed by spraying water as the granulating liquid.
• f) A water-dispersible granulate is also obtained by adding 25 parts by weight of active compounds A + B,
  5 parts by weight of 2,2′-dinaphthylmethane-6,6′-disulfonic acid sodium,
  2 parts by weight of oleoylmethyl tauric acid sodium,
  1 part by weight of polyvinyl alcohol,
  17 parts by weight of calcium carbonate and
  50 parts by weight of water are homogenized and pre-comminuted on a colloid mill, then ground on a bead mill and the suspension thus obtained is atomized and dried in a spray tower using a single-component nozzle.

Biological examples 1. Pre-emergence weed action

Seeds or rhizome pieces of, mono- and dicotyledonous weed plants are grown in Plastic pots of 9 cm in diameter laid out in sandy loam and with soil  covered. Weeds found in rice cultivation are mixed with water saturated soil, with enough water being poured into the pots that the Water to the surface of the ground or a few millimeters above it.

Formulated in the form of wettable powders or emulsion concentrates Active ingredient combinations according to the invention and in parallel experiments correspondingly formulated individual active ingredients are then aqueous suspensions or emulsions with a water application rate of the equivalent of 600 to 800 l / ha in different doses on the surface of the covering soil applied or poured into irrigation water with rice.

After the treatment, the pots are placed in the greenhouse and under good growing conditions for the weeds. The optical rating of the Plant damage or the emergence damage occurred after the emergence of the Test plants after a test period of 3 to 4 weeks compared to untreated controls. The herbicidal compositions according to the invention have a good herbicidal pre-emergence activity against a wide range of grass weeds and weeds.

In all cases, the combinations between the calculated and the differentiated efficiency found. The calculated, theoretically too The expected efficiency of a combination is determined using the formula from S. R. Colby: Calculation of synergistic and antagonistic responses of herbicide combinations, Weeds 15, pages 20-22 (1967).

For combinations of two, this formula is:

and accordingly for the combination of three herbicidal active ingredients:

in which
X =% damage by herbicide A at x kg / ha application rate;
Y =% damage by a herbicide B at a rate of y kg / ha;
Z =% damage by a herbicide C at a rate of application of z kg / ha;
E = the damage to be expected from the herbicides A + B (or + C) at x + y (or + z) kg / ha.

If the actual damage is greater than the calculated damage, it is Effect of the combination more than additive, d. H. it is a synergistic Effect before.

The active compound combinations according to the invention have a herbicidal action which is higher than due to the observed effects of the individual components sole use according to Colby is expected. The drug combinations are thus synergistic.

2. Post-emergence weed action

Seeds or rhizome pieces of monocotyledonous and dicotyledonous weeds are grown in Plastic pots laid out in sandy clay soil, covered with earth and in Greenhouse grown under good growing conditions. In rice growing occurring weeds are grown in pots in which water up to Stands 3 cm above the surface of the soil, and cultivated during the experimental phase.

Approx. two to three weeks after sowing, the test plants are Three-leaf stage treated.  

The formulated according to the invention as wettable powder or as emulsion concentrates Active ingredient combinations and the correspondingly formulated in parallel experiments Individual active ingredients are in different doses with a water application rate sprayed from the equivalent of 300 to 600 l / ha onto the green parts of the plant and after approx. 3 up to 4 weeks standing time of the test plants in the greenhouse under optimal wax conditions the effect of the preparations visually compared to untreated Controls rated. With weeds that occur in rice cultivation, the effects substances are also added directly to the irrigation water (application in analogy to the so-called called granulate application) or sprayed on plants and in irrigation water. The Agents according to the invention have good herbicidal activity even after emergence against a wide range of economically important grasses and weeds. The Effects of the agents according to the invention are synergistic according to the Colby analysis.

3. Crop tolerance

In further experiments in the greenhouse, seeds of a larger number of Cultivated plants and weeds laid out in sandy loam soil and covered with soil covers. Rice is grown and cultivated as water rice in the water-saturated soil.

Some of the pots are immediately treated as described under 1., the others in Set up the greenhouse until the plants have developed two to three real leaves and then with the active ingredient combinations according to the invention and for comparison only with a single active ingredient in different dosages, as described under 2 sprays. In the case of water rice, application is also partially carried out by pouring the active ingredients or their formulation in the irrigation water.

Two weeks after application and standing in the greenhouse, the Assessment found that the active ingredient combinations according to the invention different Cultures in the pre- and post-emergence process even with high active ingredient doses leave undamaged. They spare Gramineae crops such as B. wheat and rice. The The active compound combinations according to the invention thus have a high selectivity  Application to combat unwanted plant growth in agricultural Cultures on.

The results of selected tests are shown in the following table:  

Table 1

Herbicidal activity against ECCR; Application in the growth stage 2.5 leaves; Assessment 15 days after application

Table 2

Herbicidal activity against ECCR; Application in the growth stage 3 leaves; Assessment 12 days after application

Table 3

Crop tolerance to transplanted rice; Application: 0 days after transplantation; Assessment 15 days after transplantation

Claims (10)

1. Herbicidal agents characterized by an effective content of

• A) Compounds of the general formula (I) or their salts wherein
  a₁) R¹ ethoxy, propoxy or isopropoxy and
  R² is halogen, NO₂, CF₃, CN, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio or (C₁-C₄-alkoxy) -carbonyl and
  n 0, 1, 2 or 3 or
  a₂) R¹ each in the 2-position on the phenyl radical - halogen, methoxy, ethyl or propyl,
  R² (C₁-C₄ alkoxy) carbonyl in 6-position in the phenyl radical and
  n = 1
  and in all cases a₁) - a₂)
  R³ is hydrogen, saturated or unsaturated C₁-C₈-alkyl or C₁-C₄-alkoxy,
  R⁴, R⁵ independently of one another hydrogen, halogen, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio, the latter three radicals being unsubstituted or substituted by halogen, C₁-C₄-alkoxy or C₁-C₄-alkylthio ,
  YO or S and
  E CH or N
  mean in combination with
• B) a compound B of formula (II) or its salts wherein
  R⁶ is hydrogen or (C₁-C₆-alkyl.

2. Composition according to claim 1, characterized in that it contains compounds of formula (I) or their salts, wherein
a₁) R¹ ethoxy, propoxy or isopropoxy and
R² is oriented in position 6 and has the meaning given above, and
n 0 or 1 or
in all cases a₁) and a₂)
R³ is hydrogen, C₁-C₄-alkyl,
R⁴, R⁵ halogen, C₁-C₄-alkyl, C₁-C₄-alkoxy or C₁-C₄-alkylthio, the latter 3 radicals being unsubstituted or substituted by halogen, C₁-C₄-alkoxy or C₁-C₄-alkylthio,
YO and
E CH mean. 3. Composition according to claim 1 or 2, characterized in that they contain compounds of the formulas A1, A2 and A3 or their salts contain. 4. Composition according to one or more of claims 1 to 3, characterized characterized in that they contain 0.1 to 99 wt .-% of active ingredients A and B in addition to conventional Formulation aids included. 5. Composition according to one or more of claims 1 to 4, characterized characterized in that they contain the active ingredients A and B in a weight ratio 1: 1 to 1:40 included. 6. Process for the preparation of an agent according to one or more of the Claims 1 to 5, characterized in that a compound A with a Compound B analogous to a conventional crop protection formulation from Group containing wettable powders, emulsifiable concentrates, aqueous solutions, Emulsions, sprayable solutions, oil or water based dispersions,  Suspension emulsions, suspension concentrates, oil-miscible solutions, Capsule suspensions, granules in the form of micro, spray, elevator and Adsorption granules, dusts, mordants, soil or scatter granules, water-dispersible granules, ULV formulations, microcapsules and waxes, formulated. 7. Process for combating undesirable plants, thereby characterized in that a herbicide on these or their cultivated areas effective amount of an agent according to one or more of claims 1 to 5 applied. 8. The method according to claim 7, characterized in that weeds in Crops are selectively controlled. 9. The method according to claim 8, characterized in that the crop of crops Rice is. 10. Use of the herbicidal compositions according to one or more of the claims 1 to 5 for selective weed control in rice.