KR100358303B1 - Compositions with synergistic herbicidal effect to inhibit unwanted weed growth in rice crops - Google Patents

Abstract

The present invention provides substituted N-phenoxysulfonyl-N '-(4,6-disubstituted pyrimid-2-yl) ureas and 2-fluoro-4-cyanophenoxyphenoxypropionic acid esters, and optionally one It relates to a herbicide composition having a synergistic effect containing the above-mentioned rice herbicide.

Description

Composition having a synergistic herbicidal effect for inhibiting the growth of unwanted weeds in rice crops

The present invention belongs to the field of plant protection agents that can be used against monocotyledonous and dicotyledonous weeds. Federal Republic of Germany Patent Application No. 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) describes heterocycle substituted phenoxysulfonylureas that can be used to control a wide range of monocotyledonous and dicotyledonous weeds. They can be used as soil herbicides and through leaves and also show particularly high selectivity in cereals, i.e. monocotyledonous crops such as corn and rice.

P 39 33 543.7, P 40 31 799.4 and P 42 09 475.5 describe mixtures of active compounds which have been shown to be synergistically successful in controlling crops, for example weeds, which are of major concern for rice. .

However, in rice, many economically important monocotyledonous weeds, for example Cyperus serotinus , Sagittaria spp., Eleocharis spp., Scirpus spp. , Echinochloa spp., Which cannot be controlled in an optimal manner using only such mixtures.

Surprisingly, weeds have distinct synergistic properties with regard to efficacy against weeds when applied in combination with the above-mentioned individual compounds in biological tests and, therefore, are superior to the mixtures described in P 39 33 543.7 and P 42 09 475.5. The active compound could be identified.

The present invention provides (A) a compound of formula (I) or salts thereof, and (B) a compound of formula (II) (I) EII-112, 2-fluoro-4-cyanophenoxy Phenoxypropionic acid ester) or a mixture of salts thereof in an effective amount.

In the above formula,

(a ₁ ) R ¹ is ethoxy, propoxy or isopropoxy,

R ² is halogen, NO ₂ , CF ₃ , CN, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -alkylthio or (C ₁ -C ₄ -alkoxy) carbonyl ,

n is 0, 1, 2 or 3, or

(a ₂ ) R ¹ in each case is halogen, methoxy, ethyl or propyl at the 2-position on the phenyl radical,

R ² is (C ₁ -C ₄ -alkoxy) carbonyl at the 6-position of the phenyl radical,

n is 1,

In the case of both (a ₁ ) and (a ₂ ),

R ³ is hydrogen, saturated or unsaturated C ₁ -C ₈ -alkyl or C ₁ -C ₄ alkoxy,

R ⁴ and R ⁵ independently of one another are hydrogen, halogen, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -alkylthio, of which the last three radicals are halogen, C ₁ -C ₄ - alkoxy or C ₁ -C ₄ - or substituted by alkylthio is unsubstituted,

Y is O or S,

E is CH or N,

R ⁶ is hydrogen or (C ₁ -C ₆ ) -alkyl.

If desired, one or more known rice herbicides (c) of the class having very different structures may be further mixed and used. Of particular interest are compounds of the sulfonylurea, urea, amide, cyclohexanedione, thiocarbamate or chloroacetanilide classes.

Specific examples of the above-mixed herbicides which may be mentioned without limitation are the following compounds.

C1, AC-014

C2, Anilofoss

C3, Ventazone

C4, bensulfuron methyl

C5, Benzophene

C6, bromobutide

C7, Butachlor

C8, Butenachlor

C9, Cynmethyline

C10, cynosulfuron

C11, α -chloro-N- (3-methoxy-2-thienyl) methyl-2 ', 6'-dimethylacetanilide (NSK-850)

C12, dimuron (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, dimethacrylate

C16, dithiopyr

C17, DPX-47

C18, esprocab

C19, 4-ethoxybenz-2 ', 3'-dihydrochloroanilide (HW-52)

C20, phenoxaprop ethyl or phenoxaprop P-ethyl

C21, imazosulfuron

C22, JC 940 (1- (2-chlorobenzyl) -3- ( α , α -dimethylbenzyl) urea

C23, MCPB

C24, mefenacet

C25. Molinate

C26, naproanilide

C27, piperofoss

C28, pretilachlor

C29, propanyl

C30, pyrazosulfuron-ethyl

C31, Pirazosifen

C32, pyrazolate

C33, Queen Clolock

C34, simethrin

C35, sulforion (chloromesulone, ICI-A0051)

C36, thioubencab

C37, (2.1-I)

However, other rice herbicides may also be advantageously used with the mixtures according to the invention.

Compound A is known from the aforementioned Federal Republic of Germany patent application. Compound B is described in European patent application EP 302 203.

In the general formulas referring to compounds A and B, stereochemistry is not mentioned in detail. When stereoisomers are produced, all geometric isomers, enantiomers and diastereomers and mixtures thereof are also included in the above general formula.

Compound DPX-47 = DPX-A8947, N-(((4,6-dimethoxypyrimidin-2-yl) aminocarboxy) -1-methyl-4- (2-methyl-2H-tetrazol-5- Il) -1-H-pyrazole-5 sulfonamide has the following structural formula.

Compound AC-014, 1- (2- (cyclopropylcarbonylphenyl) sulfamoyl) 3 (4.6 dimethoxypyrimidin-2-yl) urea has the formula: U.S. Patent 5,009,699 (1990. 6. 22).

Compound JC 940 is described in Japanese Patent Application No. J-60087254.

Compound imazosulfuron (TH-913) is described in patent application EP-A-0 238 070 (see Example 1).

Compound NSK-850 ( α -chloro-N- (3-methoxy-2-thienyl) -methyl-2 ', 6' dimethylacetanilide) is described in M. Ogasawara et al. ", (Tokyo), 1989, pp 131-137.

Compound HW-52 (4-ethoxybenz-2,3-dihydrochloroanilide) is described by N. Ichizen et al., "Weed Research", (Tokyo), 1990, pp 261-267. It is described in

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

Compound sulfotions (chloromesulone, 2- (2-chloro 1-mesylbenzoyl) cyclohexane-1,3 dione) are described in EP 0 298 680 (see compound number 51A on page 13). Other compounds of type C are described in "The Pesticide Manual", British Crop Protection Council, 9th Ed., 1991.

Especially

(a ₁ ) R ¹ is ethoxy, propoxy or isopropoxy,

R ² is present at the 6 position and has the abovementioned meaning,

n is 0 or 1,

in both (a ₁ ) and (a ₂ )

R ³ is hydrogen, C ₁ -C ₄ -alkyl, in particular hydrogen or methyl,

R ⁴ and R ⁵ are halogen C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy or C ₁ -C ₄ -alkylthio, the last one of which is halogen, C ₁ -C ₄ -alkoxy or Unsubstituted or substituted by C ₁ -C ₄ -alkylthio,

Y is O

E is CH

Of interest are the herbicide compositions according to the invention containing the compounds of formula (I) or salts thereof.

Saturated or unsaturated alkyl and alkoxy are the corresponding straight or branched alkyl or alkoxy and halogen is F, Cl, Br or I, preferably F or Cl.

Compounds of formula (I) may form salts in which hydrogen of the —SO ₂ —NH group is substituted by a cation suitable for agricultural use. In general, the salts are metal salts, in particular alkali metal salts, alkaline earth metal salts, optionally alkylated ammonium salts or organic amine salts.

As compound A, preferred herbicide compositions contain one or more compounds of the following general formulas (A1), (A2) and (A3).

Specific examples of mixtures of the active compounds claimed herein, which may be mentioned without limitation, are as follows.

A ₁ + B

2.A ₁ + B + C10 (NSK 850)

3.A ₁ + B + C11 (CH 900)

4.A ₁ + B + C25 (Pretilachlor)

When applied together, the mixtures according to the invention show very good activity against a number of economically important monocotyledonous and dicotyledonous weeds. Difficult to control perennial weeds, from rhizomes, roots or other permanent organs, are easily overcome by a mixture of active compounds. It is not important whether the mixture is applied before sowing, before germination or after germination. The monocotyledonous and dicotyledonous weeds that can be controlled by the composition according to the present invention are not limited to a particular kind and some representative examples may be mentioned in more detail by the examples.

During the year, monocotyledonous weed species, such as Echinochola and Cyperus species and perennial species, ie cold tolerant cypressus species, are readily controlled.

Weeds grown in rice under certain crop conditions, for example, fructose , Alisma , Rotala , Monochoria , Eleocharis , sirpus , cypressus and the like according to the invention It is controlled in an excellent way by mixtures of the active compounds.

When the herbicide composition according to the present invention is applied to the soil surface before germination, germination of weed seedlings is completely inhibited, or weeds grow up to the cotyledon stage, but soon their growth stops and finally dies after 3-4 weeks. .

Application of the mixture of the active compounds according to the invention to parts of green plants or to irrigation water after rice crop germination stops growth very rapidly after treatment. Weeds remain in the growth stage of application, or die somewhat quickly after a certain period of time, so that competitive weeds harmful to crops can be removed very early by continuing to use the novel compositions according to the present invention.

The composition according to the invention has excellent herbicidal activity against monocotyledonous and dicotyledonous weeds, but only slightly or no damage to crop rice. For this reason, the present compositions are particularly well suited for selectively controlling unwanted plant growth in rice.

The compositions are superior to known herbicides and mixtures thereof with respect to various functions and efficacy and can be used at low application rates. Another advantage of the new mixtures is their continuous action, which lasts for several weeks, eliminating the need for subsequent application of herbicides to prevent weeds from germinating. In other words, the growth of competing weeds can be eliminated in one application, so there is no need to process them again.

With the mixture of the active compounds according to the invention, the herbicidal action is achieved beyond what is expected on the basis of the action of the individual components. Thus, the use of such mixtures can significantly reduce the amount of individual active compound used. The use of a mixture of herbicides can also speed up the action. This property provides a significant benefit to the user when actually controlling weeds. Users can control weeds more cheaply, faster, and with less effort, more permanently, resulting in greater yields in one crop group.

It has also been found that in the mixture of many active compounds there is a considerable degree of action of a toxic agent or antidote. That is, it has been found that the phytotoxic side effects of the active compounds used can be reduced or completely avoided in crops such as rice.

Mixing ratios A: B can vary within a wide range and are generally from 1: 1 to 1:40. The choice of mixing ratio depends on the mixture partner, weed growth stage, weed range and climatic conditions.

Preferably, an A: B mixing ratio of 1: 5 to 1:30 is used. The application rate of herbicide A in the mixture of active compounds is preferably 10 to 100 g active substance / ha, and the application rate of B is 50 to 600 g active substance / ha. The application rates of the compounds in group C are very different because they are a class with partially different structures and are in the range of some g to 3 kg of active substance / ha depending on the active compound.

The mixture of the active compounds according to the invention can be present as a mixture of two components and applied in a conventionally diluted form with water, or can be prepared as a so-called tank mixture by diluting separately formulated components with water.

Compounds A and B or mixtures thereof with C can be formulated in a variety of ways depending on the biological and / or physicochemical parameters described.

Suitable formulation candidates are for example: wettable powder (WP), water soluble powder (SP), water soluble concentrate, emulsifiable concentrate (EC), aqueous solution (SL), emulsion (EW) (e.g. oil-in-water and Water-in-oil emulsions, sprays or spray emulsions, oily or aqueous dispersions, suspension concentrates (SC), (suspension emulsions), oil-miscible solutions, capsule suspensions (CS), dust (DP), seed-dressing agents , Soil-applying or spraying granules, micro-type granules, spray, absorbent and adsorbent granules (GR), water-soluble granules (SG), water dispersible granules (WG), ULV blends, microcapsules or waxes.

Such individual types of formulations are known in principle and are described, for example, in Waencker-Kunchler, "Chemische Technologic" (Chemical Technology), Volume 7, C. Hauser Verlag Munich, 4th edition 1986. ]; Van Valkenburg, “Pesticide Formulations”, Marcel Dekker N.Y., 2nd Ed. 1972-73; K. Martens, "Spray Drying Handbook", 3rd Ed. 1979, G. Goodwin Ltd. London.

Necessary formulation aids such as inert materials, surfactants, solvents and other additives are known and are described, for example, in Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd, Ed., Darland Books , Caldwell NJ; H. V. Olphen, "Introduction to Clay Colloid Chemisty", 2nd Ed., J. Wiley Sons, N.Y., Marsden, "Solvents Guide", 2nd Ed., Interscience, N.Y. 1950; McCutcheon, "Detergents and Emulsifiers Annual", NC Publ. Corp., Ridgewood N. J .; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., N.Y. 1964; Schonfeldt, "Grenzflachenaktive Athylenoxidaddukte" (Surface-Active Ethylene Oxide Adducts), Wiss. Verlagsgesell., Stuttgart 1976; Binnacker-Kuchler, "Chemische Technologie" (Chemical Technology), Volume 7, C. Hauser Verlag Munich, 4th edition 1986.

On the basis of the combinations, mixtures with other pesticidal active substances such as other herbicides, fungicides or pesticides, and also fertilizers and / or growth regulators can be prepared, for example, in the form of the final formulation or in a tank mixture.

Wettable powders may be uniformly dispersed in water and, in addition to the active compounds, with the exception of diluents or inert materials, are ionic and / or nonionic surfactants (wetting agents, dispersants), for example polyoxyethylenated alkylphenols, polyoxy Ethylenated fatty alcohols or fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, sodium lignosulfonates, sodium 2,2'-dinaphthylmethane-6,6-disulfonates, It is a formulation containing sodium dibutylnaphthalenesulfonate or optionally sodium oleoylmethyl taurate. To prepare the wettable powder, the herbicidally active compound is finely ground using, for example, a conventional apparatus such as a hammer mill, blow mill or air jet mill and mixed simultaneously or subsequently with a compounding aid.

Emulsifiable concentrates contain the active compound in an organic solvent such as butanol, cyclohexanone, dimethylformamide, xylene or alternatively relatively high boiling aromatics, with the addition of one or more ionic and / or nonionic surfactants (emulsifiers). Or dissolved in hydrocarbon. Emulsifiers which may be used are, for example, alkylarylsulfonic acid calcium salts, for example Ca dodecylbenzenesulfonate or nonionic emulsifiers, for example fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene Oxide-ethylene oxide condensates, alkyl polyethers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters or polyoxyethylene sorbitol esters.

Dust compositions may comprise finely divided solid materials of the active compound, such as talc: natural clays such as kaolin, bentonite and pyrophyllite; Or by grinding with diatomaceous earth.

Suspension concentrates are aqueous or oily. They can be prepared, for example, by means of commercially available bead mills, by wet polishing, for example with the addition of any surfactant as already mentioned for other formulation types.

Emulsions, for example oil-in-water emulsions (EW), can be prepared by means of stirrers, colloid mills and / or static stirrers using, for example, any surfactants and aqueous organic solvents such as those already mentioned for other formulation types. It can manufacture.

The granules may be sprayed onto the granulated adsorptive inert material or the concentrate of the active compound may be sprayed onto the granulated adsorptive inert material by means of an adhesive such as polyvinyl alcohol, sodium polyacrylate or optionally mineral oil such as sand, kaolinite or granulated inert material. It can be prepared by applying to the surface of the carrier. Suitable active compounds may also be granulated, optionally in a mixture with fertilizers, in a manner conventional for the preparation of fertilizer granules.

In general, water-dispersible granules are prepared by conventional methods such as spray drying, fluid bed granules, disc granules, mixing using a high speed mixer and solid free extraction.

Agrochemical formulations generally contain from 0.1 to 99% by weight, in particular from 2 to 95% by weight of active compounds A and B and optionally C. The concentration of active compounds A, B and C in the combination may vary.

In wettable powders, the active compound concentration is, for example, about 10-95% by weight in 100% by weight, with the remainder being a conventional blending component. For emulsifiable concentrates, the concentration of the active compound may be about 1 to 85% by weight, preferably 5 to 80% by weight. The formulation in dust form contains from about 1 to 25% by weight at most 5 to 20% by weight of active compound, and the spray solution contains from about 0.2 to 25% by weight, preferably 2 to 20% by weight of active compound. In the case of granules, such as water-dispersible granules, the active compound content depends in part on whether the active compound is present as a liquid or as a solid and whether granular aids and fillers are used. Generally, for water-dispersible granules, the content is 10 to 90% by weight. In the case of sparge granules which are directly sprayed onto irrigation water, they are generally from 1 to 10% of active compound.

Combinations of the active compounds mentioned also include, in each case, conventional adhesives, wetting agents, dispersants, emulsifiers, penetrants, preservatives, cryoprotectants and solvents, fillers, carriers and colorants, antifoaming agents, evaporation control agents and pH- and viscosity-increasing agents. Optionally contains.

In application, the formulations present in the commercially available form are optionally diluted in conventional manner, for example with wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules. It is common for the preparations in the form of dust, soil or spray granules and spray liquids to be no longer diluted with further inert substances before application.

The required application rates of compounds A and B vary depending on external conditions such as temperature, humidity and type of herbicide used. The necessary application rate of the rice herbicide (C) additionally used depends on external conditions.

The following examples are intended to illustrate the invention.

A. Formulation Examples (Combination Examples)

(a) A dust composition was obtained by mixing 10 parts by weight of a mixture of the active compounds according to the invention and 90 parts by weight of talc as an inert material and grinding with a hammer mill.

(b) Easily water-dispersible wettable powder liquid, 25 parts by weight of active compound A + B, 64 parts by weight of kaolin-containing quartz as inert material, 10 parts by weight of potassium lignosulfonate, and sodium oleoyl as wetting agent and dispersant 1 part by weight of methyltaurate was mixed and obtained by grinding on a pin disk mill.

(c) easy to be - ^(? Triton (Triton) × 207) a dispersible dispersion concentrate, the active compounds A + B 20 parts by weight of alkylphenol polyglycol ether 6 parts by weight, isophthalic tree decanol polyglycol ether (8 EO) Obtained by mixing 3 parts by weight and 71 parts by weight of paraffinic mineral oil (boiling point, for example about 255 to 277 ° C.) and polishing with a wear ball mill to a precision of 5 microns or less.

(d) An emulsifiable concentrate was 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 emulsifier.

(e) The water dispersible granules were mixed with 75 parts by weight of active compound A + B, 10 parts by weight of calcium lignosulfonate, 5 parts by weight of sodium lauryl sulfate, 3 parts by weight of polyvinyl alcohol and 7 parts by weight of kaolin, and Obtained by grinding in a disk mill and spraying water as granulation liquid to granulate the powder in a fluidized bed.

(f) 25 parts by weight of the active compound A + B, 5 parts by weight of sodium 2,2'-dinaphthylmethane 6,6'-disulfonate, 2 parts by weight of sodium oleoylmethyltaurate, 1 part by weight of polyvinyl alcohol, 17 parts by weight of calcium carbonate and 50 parts by weight of water are homogenized and prepulverized, ground in a bead mill, sprayed, and the resulting suspension is obtained by drying in a spray tower with one material nozzle. .

B. Biological Examples

1. Herbicide before germination

Some of the seeds or rhizomes of monocotyledonous and dicotyledonous weeds were placed in sandy loam soil in a plastic pot 9 cm in diameter and covered with soil. Weeds growing on rice cultivation were grown in water-saturated soils, and pots were filled with water to or even up to several millimeters above the soil surface.

The mixtures of the active formulations according to the invention in the form of wettable powders or emulsifiable concentrates and similar tests are applied to the surface of the soil covered with the respective active compounds correspondingly formulated, or from 600 to 800 l / ha for rice. Pour irrigation water was poured in different application amounts as aqueous suspensions or emulsions at corresponding water application rates.

After treatment, the pots were kept in greenhouses under good growth conditions in the weeds. Visual assessment of plant damage or germination damage was performed after germination of the test plants after a 3-4 week test period compared to the untreated control. The herbicide compositions according to the invention have good pre-germination herbicidal activity against a wide range of grass weeds and weeds.

In all cases, the functionality of the mixture differs between the calculated and measured values. The theoretically expected calculation of the functionality of the mixture is determined by the formula of S. R. Colby: Calculation of synergistic and antagonistic responses of herbicide combinations, Weeds 15, pp 20-22 (1967).

The formula is as follows for a mixture of two components:

The mixture of three herbicidal active compounds is as follows:

In the above formula,

X =% damage by herbicide A at X kg / ha application rate;

Y =% damage by herbicide B at application rate of Y kg / ha;

Z =% damage by herbicide C at application rate Z kg / ha;

E = rate of damage expected by herbicides A-B (or + C) at X + Y (or X + Y + Z kg / ha application rate).

If the actual damage rate is greater than what is arithmetically expected, the action of the mixture is greater than the combined action of each component. In other words, there is a synergistic effect.

The mixture of active compounds according to the invention has a higher herbicidal action than expected based on the action observed when the individual components are applied alone (calculated according to Colby's formula). The mixture of active compounds is therefore synergistic.

2. Herbicide action after germination

Some of the seeds or rhizomes of monocotyledonous and dicotyledonous weeds were placed in sandy loam soil in plastic pots, covered with soil and grown in greenhouses under good growth conditions. Weeds growing on rice cultivation were grown in pots with water up to 3 cm above the soil surface, and during the trial phase. About 2 to 3 weeks after sowing the test plants were treated at the 2 to 3 leaf stage.

The mixtures of the active compounds according to the invention in the form of wettable powders or emulsifiable concentrates and the corresponding active compounds in similar tests were tested for greenhouse plants at various dosages at water application rates of 300 to 600 l / ha. Some were sprayed and the action of the formulation was visually evaluated in comparison with the untreated control after the test plants were left in the greenhouse for about 3-4 weeks under optimal growth conditions. In the case of rice or weeds growing on rice fields, the active compounds were added directly to irrigation water (similar to so-called granulation applications) or plants and sprayed on irrigation water. The composition according to the invention has good herbicidal activity against a wide range of economically important grass weeds and weeds even after germination. The action of the composition according to the invention is synergistic according to Colby analysis.

3. Crop Resistance

In further tests in the greenhouse, relatively large numbers of crops and weed seeds were placed in sandy loam soil and covered with soil. Rice was grown and grown with paddy rice in soil saturated with water.

Several pots are immediately treated as mentioned in 1 above, the rest are placed in a greenhouse until the plants grow to 2-3 leaves, followed by a mixture of the active compounds according to the invention as mentioned in 2 above, And sprayed with only one individual active compound in different application amounts for comparison. In the case of rice, the application was also carried out in some cases by pouring the active compound or combination thereof into irrigation water.

Two weeks after application and standing in the greenhouse, it was found by visual evaluation that the mixture of active compounds according to the invention does not damage various crops before and after germination even at high application amounts of the active compounds. Mixtures of the active compounds protect Gramineae crops such as wheat and rice. The mixture of active compounds according to the invention therefore has high selectivity when applied to inhibit the growth of undesirable plants in crops.

In the following, the results of the screening test are presented in a table.

Table 1: Action of herbicides on ECCR;

Application at the stage where 2.5 leaves grow;

15 days after application

Abbreviation:

a.j. = Active substance (for pure active compound)

ECCR = Echinochola cruss galli

A1 = 1-[(2-ethoxyphenoxy) sulfonyl] -3- (4,6-dimethoxypyrimidinyl) urea as wettable powder of 20% strength

B = DEH 112 as an emulsifiable concentrate of 10% strength

C2 = Anilofos as wettable powder of 10% strength

% Damage = 0-100: No Damage-Completely Damaged

Table 2: Action of herbicides on ECCR

Application at the stage where three leaves grow;

12 days after application

Abbreviation:

a.j. = Active substance (for pure active compound)

ECCR = Echinokloa Cress Galli

A1 = 1-[(2-ethoxyphenoxy) sulfonyl] -3- (4,6-dimethoxypyrimidinyl) urea as wettable powder of 20% strength

B = DEH 112 as an emulsifiable concentrate of 10% strength

C2 = Anilofos as wettable powder of 10% strength

% Damage = 0-100: No Damage-Completely Damaged

Table 3: Suitability of Crops for Transplanted Rice;

Application: Day 0 post transplant;

Evaluation: 15 days after transplantation

Abbreviation:

Active substance (for pure active compound)

Transplanted rice = paddy rice (variety: Nihonbare)

A1 = 1-[(2-ethoxyphenoxy) sulfonyl]-(4,6-dimethoxypyrimidinyl) urea as wettable powder of 20% strength

B = DEH 112 as an emulsifiable concentrate of 10% strength

C2 = Anilofos as wettable powder of 10% strength

G = growth inhibition rate

0-10: No damage-completely damaged

Weight of eggplant = weight evaluation of rice crops to untreated rice plants (%)

SD = standard deviation of the mean

Claims (8)

(A) the compound of formula (I) or a salt thereof, and (B) the compound of the following general formula (II) or a salt thereof Herbicide composition comprising a mixture of 1: 1 to 1:40 in a weight ratio of (A) :( B): In the above formula, (a ₁ ) R ¹ is ethoxy, propoxy or isopropoxy, R ² is halogen, NO ₂ , CF ₂ , CN, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -alkylthio or (C ₁ -C ₄ alkoxy) carbonyl, n is 0, 1, 2 or 3 or (a ₂ ) R ¹ in each case is halogen, methoxy, ethyl or propyl at the 2-position on the phenyl radical, R ² is (C ₁ -C ₄ -alkoxy) carbonyl at the 6-position of the phenyl radical, n is 1, In the case of both (a ₁ ) and (a ₂ ), R ³ is hydrogen, saturated or unsaturated C ₁ -C ₈ -alkyl or C ₁ -C ₄ -alkoxy, R ⁴ and R ⁵ independently of one another are hydrogen, halogen, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy or C ₁ -C ₄ -alkylthio, of which C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy and C ₁ -C ₄ -radicals are unsubstituted or substituted by halogen, C ₁ -C ₄ -alkoxy or C ₁ -C ₄ -alkylthio, Y is O or S, E is CH or N, R ⁶ is hydrogen or (C ₁ -C ₆ ) -alkyl. The method of claim 1, (a ₁ ) R ¹ is ethoxy, propoxy or isopropoxy, R ² is present at position 6 and has the meaning defined in claim 1, n is 0 or 1, In the case of both (a ₁ ) and (a ₂ ), R ³ is hydrogen or C ₁ -C ₄ -alkyl, R ⁴ and R ⁵ are halogen, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy or C ₁ -C ₄ -alkylthio, of which C ₁ -C ₄ -alkyl, C ₁ -C _4- Alkoxy and C ₁ -C ₄ -alkylthio radicals are unsubstituted or substituted by halogen, C ₁ -C ₄ -alkoxy or C ₁ -C ₄ -alkylthio, Y is zero, E is CH A composition containing a compound of formula (I) or a salt thereof. The method according to claim 1 or 2, A composition containing a salt of a compound or ion of the following formulas (A1), (A2) and (A3). The method according to claim 1 or 2, A composition comprising from 0.1 to 99% by weight of a mixture of active compounds (A) and (B) with conventional compounding aids. Wettable powders, emulsifiable concentrates, aqueous solutions, emulsions, sprayable solutions, oily or aqueous dispersions, suspension emulsions, suspension concentrates, oil-miscible solution capsule suspensions, microscopic granules, sprays, absorbent and adsorbent granules, dust compositions, seed dressings Comprising combining compound (A) with compound (B), similar to conventional plant protection agent combinations selected from the group consisting of compositions, soil-applying or spraying granules, water dispersible granules ULV blends, microcapsules and waxes, A process for preparing a composition according to claim 1. A method of controlling unwanted weeds, comprising applying the composition according to claim 1 to unwanted weeds or their habitat. The method of claim 6, How to selectively control weeds from useful plant crops The method of claim 7, wherein How useful plant crops are rice.