JPH06128106A - Herbicidal composition - Google Patents

Abstract

PURPOSE: To obtain a herbicide comspn. capable of selectively controlling weeds growing around culture crops, especially a rice plant and producing a synergistic effect. CONSTITUTION: This herbicide comspn. contains an effective amt. of a compd. represented by the formula or its salt is combination with at least one of 24 kinds of compds. such as butachlor, mefenacet, esprocarb, butenachlor, molinate, thiobencarb, dimepiperate, NSK-850, pyrazolynate, naproanilide and bensulfuron- methyl. In the formula, R<1> is a halogen, alkoxyl, (halo)alkyl, NO2 , CN or S(O)n R<10> (0<=n<=2 and R<10> is an alkyl, alkoxyl, etc.), each of R<2> and R<3> is H, a halogen a (halo)alkyl, a (halo)alkoxyl, CN, NO2 , S(O)m -R<11> (0<=m<=2 and R<11> is an alkyl, phenyl, benzyl, etc.), NR<12> R<13> (each of R<12> and R<13> is H or an alkyl), etc., R<4> is H, an alkyl or a CO-O-alkyl, each of R<5> -R<9> is H, an alkyl, etc.

Description

Detailed Description of the Invention

FIELD OF THE INVENTION The present invention relates to a herbicidal composition for controlling weeds in cultivated crops, especially rice crops.

2. Description of the Related Art WO91 / 05469 and WO91 /
05470 discloses combinations of herbicidal compositions and active substances which can be used for controlling unwanted plants in rice production. These herbicidal compositions include
Also included are synergistically effective mixtures to control a wide range of monocotyledonous and dicotyledonous weeds in rice cultivation.

However, in rice cultivation in Japan and Southeast Asia, weeds that are not sufficiently controlled even when such a combination is used are known. These are especially the species of stupid fish (Sagittaria spp.), Black eye (Eleocaris kuroguwa).
i) and broadleaf are also included.

Surprisingly, the present inventors have found that when used together in biological greenhouse experiments with a wide range of herbicidally active substances, a wide variety of weeds were identified. A new synergistically effective combination of active substances has been found, which has a very excellent action and is extremely tolerant to rice. They are superior in their range of action and effect to known herbicides and herbicidal compositions and can be used in low dosages. Another advantage of these novel combinations is their duration of action, which lasts for several weeks and thus saves further application of herbicides to newly germinated weeds. 1
The fact that one application is sufficient for weed growth makes the second application unnecessary. The present invention provides compounds of formula I or salts thereof (compounds of type A):

[Chemical formula 26] (In the above formula, R ¹ is halogen, (C ₁ -C ₄ ) -alkoxy,
(C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -haloalkyl,
NO _2, -CN, or ^{_{S (O) n R 10;}} R 2 and R ³ are each independently of the other hydrogen, halogen, (C ₁ -C ₄₎ -
Alkyl, (C ₁ -C ₄ ) -alkoxy, (C ₁ -C ₄ ) -haloalkoxy, (C ₁ -C ₄ ) -haloalkyl, -CN, -N
_{O 2, -S (O) m} - R 11, -NR 12 R 13, -NR 14 -
Be a CO- R ^15; R ⁴ is hydrogen, (C ₁ -C ₄₎ - alkyl or _{-CO -O- (C 1 -C 4)} - is alkyl; R ^5, R
⁶ , R ⁷ , R ⁸ and R ⁸ are independently of each other hydrogen or (C
₁ -C ₄₎ - alkyl, or -CO -R ^6; R ¹⁰ is (C ₁ -C ₄₎ - alkyl, (C ₁ -C ₄₎ - haloalkyl or (C ₁ -C ₄₎ - alkoxy R ¹¹ is (C ₁ -C ₄ )-
Alkyl, (C ₁ -C ₄ ) -haloalkyl, phenyl, benzyl or —NR ¹⁷ R ¹⁸ ; R ¹² and R ¹³ independently of one another are hydrogen or (C ₁ -C ₄ ) -alkyl; R
¹⁴ is hydrogen or (C ₁ -C ₄ ) -alkyl; R ¹⁵ is (C ₁ -C ₄ ) -alkyl; R ¹⁶ is hydrogen, (C ₁ -C ₄ ).
-Alkyl, (C ₁ -C ₄ ) -haloalkyl or (C ₁ -C
₄ ) -alkoxy; R ¹⁷ and R ¹⁸ are independently of each other hydrogen or (C ₁ -C ₄ ) -alkyl and n and m are independently of each other 0, 1 or 2) Of a compound or a salt thereof (A-type compound), the following compound B1) butachlor, N (butoxymethyl) -2-chloro
-N- (2,6-diethylphenyl) -acetamide

[Chemical 27] B2) Pretilachlor, N- (2-propoxyethyl)-
2-chloro-N- (2,6-diethyl-phenyl) -acetamide

[Chemical 28] B3) Mefenaset, 2- (1,3-benzothiazole
-2-yloxy) -N-methyl-acetanilide

[Chemical 29] B4) Esplocarb, S-benzyl N-ethyl-
(1,2-Dimethyl-propyl) -thiocarbamate

[Chemical 30] B5) Butenachlor, (Z) -N-but-2-enyloxymethyl-2-chloro-2 ′, 6′-diethylacetanilide, KH-218

[Chemical 31] B6) Molinate, N- (ethylthio-carbonyl) -azepan

[Chemical 32] B7) Thioben curve, (bench off curve), S-4-
Chlorobenzyl N, N-diethylthiocarbamate

[Chemical 33] B8) Dimepiperate (MY-93), N- (2-phenyl-prop-2-ylthiocarbonyl) piperidine

[Chemical 34] B9) NSK-850, α-chloro-N- (3-methoxy
-2-thienyl) -methyl 2 ', 6'-dimethylacetanilide

[Chemical 35] B10) Pyrazolinate, 4- (2,4-dichlorobenzoyl) -1,3-dimethylpyrazol-5-yltoluene
-4-sulfonate

[Chemical 36] B11) Naproanilide, 2- (2-naphthyl) propionanilide

[Chemical 37] B12) Bensulfuron-methyl, α- (4,6-dimethoxypyrimidin-2-yl-carbamoyl-sulfamoyl) -O-toluic acid

[Chemical 38] B13) Pyrazosulfuron-ethyl, 5- (4,6-dimethoxypyrimidin-2-yl (carbamoylsulfamoyl) -1-methylpyrazole-4-carboxylic acid

[Chemical Formula 39] B14) Cinosulfuron, 3- (4,6-dimethoxy-
1,3,5-Triazin-2-yl-1- [2- (2-methoxyethoxy) -phenylsulfonyl] urea

[Chemical 40] B15) Imazosulfuron, N- (2-chloro-imidaza [1,2-α] pyridin-3-yl-sulfonyl) -N'-
(4,6-dimethoxy-2-pyrimidinyl) -urea (TH-
913, Example 1 of European Patent No. 0,238,070).

[Chemical 41] B16) H1,3- (4,6-dimethoxypyridine-2-
Yl) -1- (2-ethoxyphenoxysulfonyl) urea,
(See German Patent Application P3816704.2, European Patent Application Publication No. 0,342,569).

[Chemical 42] B17) Pyrazoxyphene, 2- [4- (2,4-dichloro-benzoyl) -1,3-dimethylpyrazol-5-yloxy] -acetophenone

[Chemical 43] B18) Benzophenap (MY71), 2- [4-
(2,4-Dichloro-m-toluoyl) -1,3-dimethylpyrazol-5-yloxy] -4'-methylacetophenone

[Chemical 44] B19) Dithiopeel, 5,5'-dimethyl 2-difluoromethyl-4-isobutyl-6-trifluoromethylpyridine-3,5-dicarbothioate

[Chemical formula 45] B20) HW52, 2 ', 3'-dichloro-4-ethoxymethoxybenzanilide (see JP-A-60-42312)

[Chemical formula 46] B21) Pyributicarb, O-3-tert-Butylphenyl 6-methoxy-2-pyridyl (methyl) thiocarbamate

[Chemical 47] B22) Anilophos, 4'-chloro-2-dimethoxyhofophinothioylthio-N-isopropylacetanilide

[Chemical 48] B23) CH900, 1- (diethylcarbamoyl) -3-
(2,4,6-Trimethylphenylsulfonyl) -1,
2,4-triazole

[Chemical 49] And B24) Daimlon, 1- (1-methyl-1-phenylethyl) -3-p-toluyl-urea

[Chemical 50] At least one compound B selected from the group consisting of
A herbicidal composition containing (B-type compound) in combination (provided that an effective amount of compound A is B1 to B4, B6 to B)
8, B17 to B20 and B22, except for the composition containing in combination with only one compound B selected from the group). All of the above compounds are “Agricultural Chemicals Manual, 9th Edition, UK Council for Crop Protection, 1991.
(The Pesticide Manual, 9th Edition, Brit. Crop. C
Ouncil, 1991) ", but as described in the patent application cited therein.
Excluding 15, B16 and B20. Compound B23 is 1
Report 1992 Brighton Crop Conservation Conference Weed Section 92
Page 3-928 (Brighton CropProt. Conf. Weeds, 19
91, p923-928). Particularly interesting herbicidal compositions according to the invention are those of the formula I
¹ is fluorine, chlorine, bromine, iodine, methoxy, nitro,
Cyano or —S (O) _n R ¹⁰ ; R ² and R ³
Independently of each other hydrogen, fluorine, chlorine, bromine, iodine,
Methyl, methoxy, trifluoromethoxy, cyano, nitro, trifluoromethyl, -SO ₂ R ¹¹ , NR
¹² R ¹³ , -N (CH ₃ )-CO- R ¹⁴ or -CO- O-
(C ₁ -C ₄ ) -alkyl and R ⁴ , R ⁵ , R ⁶ , R ⁷ , R
⁸ and R ⁹ independently of one another are hydrogen or methyl, and R ¹⁰ , R ¹¹ , R ¹² , R ¹³ R ¹⁴ and n are of the abovementioned formula I compounds or salts thereof It is a herbicide composition containing. Particularly preferred herbicidal compositions according to the invention are those in which R ² and R ³ independently of one another are hydrogen, fluorine, chlorine, bromine, N (CH ₃ ) ₂ , methoxy, nitro, —SO ₂ CH ₃ , SO ₂ CH ₂ Cl, -S
O ₂ N (CH ₃ ) ₂ or trifluoromethyl and n is 2 and R ¹ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ and R ⁹ are of the formula It contains a compound represented by I. The compounds of formula I exist in different tautomeric structures (keto-enol type tautomerism) and have a strongly acidic hydrogen atom on the methine group between the three carbonyl groups. , It can be replaced by agriculturally suitable cations. The resulting salt is generally a metal salt, especially an alkali metal salt, an alkaline earth metal salt,
An optionally substituted or unsubstituted ammonium salt,
A sulfonium salt or a phosphonium salt, where the substituents can be aliphatic or aromatic. Suitable bases for the preparation of the salts according to the invention are, for example, alkali metal carbonates such as potassium carbonate, alkali metal hydroxides and alkaline earth metal hydroxides, ammonia or ethanolamine. An alkyl group shall mean a group having the indicated number of carbons. These groups may be linear or branched. Examples of the most frequently used groups are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl.
Halogen shall mean fluorine, chlorine, bromine or iodine. Haloalkyl groups may be mono- or poly-substituted by halogen, ie they may be perhalogenated. An example of a particularly preferred compound of formula I in a herbicidal mixture according to the invention is 2- (2-chloro-4-methylsulfonylbenzoyl)-
1,3-Cyclohexanedione (A1) 2- (2-Nitrobenzoyl) -4,4-dimethyl-1,3
-Cyclohexanedione (A2) and 2- (2-nitrobenzoyl) -5,5-dimethyl-1,3
-Cyclohexanedione (A3). The 2-benzoylcyclohexanedione derivative of the formula I can be obtained, for example, from the abovementioned European patent application publication no.
137,963, 0,186,118, 0,274,634 and 0,298,680 and U.S. Pat. No. 4,780,127, or they are It can be produced by the methods described in these publications. The following are given as non-limiting examples of specific mixtures of active substances according to the invention: A ₁ + Bensulfuron-methyl A ₁ + 〃 〃 + Mefuenasetto (mefenacet) A ₁ + undefined undefined + butachlor (butachlor) A ₁ + undefined undefined + Esupuro curve (esprocarb) A ₁ + undefined undefined + Purechirakuroru (pretilachlor) A ₁ + undefined undefined + molinate (molinate) A ₁ + undefined undefined + Butenakuroru (butenachlor) A ₁ + undefined undefined + bench A curve (benthiocarb) A ₁ + undefined undefined + dimepiperate (dimepiperate) A ₁ + undefined undefined + NSIY- 850 A ₁ + undefined undefined + Jichiopiru (dithiopyr) A ₁ + undefined undefined + NW 52 a ₁ + undefined undefined + Piribuchikabu (pyributicarb) a ₁ + undefined undefined + anilofos (anilofos) mixture of the following containing up to a ₁ + undefined undefined + CN 900 4 component also possible der ,
Excellent herbicidal effect in biological experiments. A ₁ + bensulfuron - methyl + dymron (daimuron) A ₁ + undefined undefined + Mefuenasetto + dymron A ₁ + undefined undefined + butachlor + dymron A ₁ + undefined undefined + Esupuro curve + dymron A ₁ + undefined undefined + pretilachlor + dymron A ₁ + undefined undefined + molinate + dymron A ₁ + undefined undefined + Butatenakuroru + dymron A ₁ + undefined undefined + thiobencarb + dymron A ₁ + undefined undefined + dimepiperate + dymron A ₁ + undefined undefined + NSK 850Tasu daimuron A ₁ + undefined undefined + Jichiopiru ＋ Dimron A ₁ ＋ 〃 〃 ＋ NW 52 ＋ Dymron A ₁ ＋ 〃 〃 ＋ Pyributi curve ＋ Dymron A ₁ ＋ 〃 〃 ＋ Animolophos ＋ Dimron A ₁ ＋ 〃 〃 + CH 900 + Dymron These two combinations are used In one respect On the one hand, dimulon improves herbicidal action against Cyperus spp. And grass weeds, on the one hand, and on the other hand dimulon also acts as a safener for crop plant rice. , And reduce the potential phytotoxicity caused by herbicides or other active substances such as sulfonylurea derivatives. However, the abovementioned mixtures can be further modified by further substituting the active substance A2 or A3 for the compound A1. Similarly, in the mixtures listed in the table above, active substance B
12 = Bensulfuron-methyl can be replaced by different sulphonylureas: B13, Pyrazosulfuron-ethyl or B14, Cinosulfuron or B
15, Imazosulfuron (TH913) or B16,
H1 or a combination of two sulfonylureas, eg B13 + B16. Similarly, one of the following herbicides:
The seeds can be mixed into a mixture of three or four instead of the sulfonylurea derivative; B10, pyrazolinate B17, pyrazoxifene B18, benzophenap B11, naproanilide. This results in a number of possibilities for combining 3 or 4 herbicidal active substances and using them together for controlling weeds in rice. The herbicidal compositions (combinations) according to the invention show a significant herbicidal action against a wide range of economically important monocotyledonous and dicotyledonous harmful plants. These active substances also germinate from rhizomes, root fragments or other perennial organs,
It also works effectively on perennial weeds that are difficult to control. In this connection, it does not matter whether the active substance is applied before sowing, before germination or after germination. In particular, some representative examples of monocotyledonous and dicotyledonous weed groups that may be controlled by the compositions according to the invention may be mentioned, but this list is not intended to be limited to a particular species. Examples of the weed species for which the composition according to the present invention acts effectively include monocotyledonous plants, such as the barnyard grass (Echinochloa) and cyperus (Cyperus sp.
p.) and of the perennial species, perennial cyperaceae. The combinations of active substances according to the invention are, for example, Urikawa (Sagittaria), Omodaka (Alisma), Yellow sedge (Rot).
It has a significant effect on the control of weeds that can be found under certain conditions of rice cultivation, such as ala), eel (Monochoria), harri (Eleocharis), firefly (Scirpus), cypress (Cyperus) and others. When the herbicide composition according to the present invention is applied to the surface of the soil before germination, the seeds of the weeds are:
Completely arrested, or weeds grow until they reach the cotyledon stage, but then they cease to grow and die completely after 3 to 4 weeks. If compositions of these active substances are applied to the green parts of the plants after germination, the growth likewise stops dramatically very shortly after treatment. Since weed plants remain in the growth stage at the time of application or they die rapidly to a greater or lesser extent after a certain period of time, the competition of weeds harmful to cultivated plants in this way is novel according to the invention. By using such a composition, it can be eliminated very early and persistently.
The composition according to the invention exhibits an excellent herbicidal action on monocotyledonous and dicotyledonous weeds, whereas the cultivated rice plant undergoes no or only negligible phytotoxicity. For these reasons, the compositions of the present invention are highly suitable for the selective control of unwanted plants in rice cultivation. The active substance combinations according to the invention make it possible to achieve herbicidal effects which far exceed those expected on the basis of the effects of the individual components. These increased effects considerably reduce the proportion of individual active substances dosed. The combination of herbicides also improves their long-lasting action or makes them act more rapidly. Such properties are of great advantage to the user when actually controlling weeds. They make weeds more economical,
It is less labor-intensive and makes it possible to control more persistently, thus allowing higher yields to be harvested on standing cultivated plants. Furthermore,
The presence of a significant detoxifying or detoxifying effect in a series of active substance combinations means that the secondary effects of phytotoxicity of the active substances used, for example in cultivated plants such as rice, are reduced or even It was found to be avoided. The proportions in which the various components are mixed can be varied within a very wide range. Their proportions depend in particular on the mixed components used, the developmental stage of the weeds, the range of the weeds and the climatic conditions. The active substances according to the invention can be present in the form of a mixed preparation of the two components, which are then diluted in water in the customary manner or applied in the form of granules. Alternatively, it may be prepared as a so-called tank mix by combining the separately formulated ingredients together and diluting with water. The compounds (combinations) can be formulated in various ways depending on the prevailing biological and / or chemo-physical parameters. Suitable possible formulations include: Wettable powders (WP), emulsions (emulsifiable concentrates) (EC), aqueous solutions (SL), emulsions such as oil-in-water and water-in-oil emulsions. (EW), spraying solutions or emulsions, oil or water based dispersions, suspoemulsions, dusts (DP), seed treatments,
But especially soil or dusting granules or water-dispersible granules (WG), ULV formulations, microcapsules or waxes. These individual formulation forms are known in principle and are described for example below:
Winnacker-Kuechler
"Chemische Technologie" Vol. 7, published by Hauser Company (C. Hauser Verlag, Muenchen) Fourth Edition 1986
Year; by Van Valkenburg
"Pesticides Formulations" Marcel Dekker NY Second Edition 1972-73
Year; Martens (K. Martens) edition "Spray Drying Handbook" (Spray Drying Handbook) 3rd edition 1979 Goodwin company publication (G. Goodwin Ltd., London). Inert substances,
Necessary formulation aids such as required formulation aids such as surfactants, solvents and other additives are likewise known and are described, for example, in the following references: Watkins (W
atkins) "Powder Diluents and Carriers for Insecticides" (Handboo
k of Insecticide Dust Diluents and Carriers) 2nd edition, published by Darland Books, Caldwell
NJ); H. v. Olphen, "Introduction to Clay Colloid Chemistry", 2nd edition, J. Wiley & Sons, NY; Marsden, "Solvent Guide." (Solvents Guide) Second edition published by Interscience, Inc. (Interscience, NY195)
0); "Detergents and Emulsifiers Annuals" MC edited by McCutcheon's
Published by MC (published by MC Publ. Corps. Ridgewood, NJ); Sisley and Wood, "Encyclopedia of Surface Active Agents" Chemical Publisher, 1964 (Chem. Publ. Co. Inc., NY);
Grenzflaechenaktive Aethylenoxi by Schoenfeldt
daddukte) Science Publishing Company, 1976 (Wiss. Verlagsgese
ll., Stuttgart) ； Winacker-Kuchler (Winnack
er-Kuechler) Co-editing "Chemical Technology (Chemische Technologie)
Volume 7: Hauser Ver. 4 (C. Hauser Verlag Muenchen)
Edition 1986. Based on these formulations, other herbicides, other pesticidally active substances such as fungicides or insecticides, and also in combination with fertilizers and / or growth regulators are also produced, for example in the form of ready mixes or tank mixes. sell. Wettable powders are preparations which can be dispersed homogeneously in water and, in addition to the active substance, also wetting agents, for example polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols or fatty amines, alkanes or alkylbenzenesulfonates. , And dispersants such as sodium glycine sulfonate, sodium 2,2′-dinaphthylmethane-6,6′-disulfonate, sodium dibutylnaphthalene sulfonate or even sodium oleylmethyl taurate, as a diluent or an inert substance. Contains with. Emulsions (emulsifiable concentrates) are prepared, for example, by adding one or more emulsifiers to the active substance in an organic solvent such as butanol, cyclohexane, dimethylformamide, xylene, or else a high-boiling aromatic or hydrocarbon. It can be manufactured by dissolving. Emulsifiers which can be used are, for example: calcium salts of alkylaryl sulphonic acids such as calcium dodecylbenzene sulphonate, or fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide / ethylene oxide condensation products, Nonionic emulsifiers such as alkyl polyethers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters or polyoxyethylene sorbitan esters. Dusts are obtained by grinding the active substance with finely divided solid substances, for example talc, for example kaolin, bentonite and naturally occurring clays such as pyrophyllite or diatomaceous earth. Granules are prepared by spraying the active substance on adsorptive granular inert substances or by adhering the active substance concentrate onto the surface of a carrier such as sand, kaolinite or granulated inert substances, for example polyvinyl alcohol, polyalcohol. It may be produced by coating with sodium acrylate, or else mineral oil. Suitable active substances can be granulated in the manner customary for the production of fertilizer granules, if desired in admixture with fertilizers. In general, the agrochemical formulations according to the invention contain from 0.1 to 99% by weight, in particular from 2 to 95% by weight, of the active substances A and B. These formulations can vary with regard to the concentrations of active substances A and B. The active substance concentration in the wettable powders is, for example, about 10 to 95% by weight, the rest up to 100% consisting of the usual formulation components. In the case of emulsions, the active substance concentration is about 1 to 85.
It may be wt%, preferably 5 to 80 wt%. Formulations in the form of powders are about 1 to 25% by weight, often 5
A spray solution containing from 20 to 20% by weight of the active substance,
It contains about 0.2 to 25% by weight, preferably 2 to 20% by weight of active substance. In the case of granules, for example water-dispersible granules, the active substance content depends in part on whether the active substance is a liquid or a solid and what granulating aids and fillers are used. It depends.
Generally, water-dispersible granules contain from 5 to 90% by weight and spreading granules contain from 1 to 50% by weight, preferably from 2 to 25% by weight of active substance. Furthermore, the abovementioned active substance formulations optionally comprise in each case adhesives, wetting agents, dispersants, emulsifiers, penetrants, solvents, fillers or carriers. The formulations, which are present in the commercially available forms, are optionally diluted in use in the customary manner, for example with water in the case of wettable powders, emulsions, dispersions and water-dispersible granules. Dusts and soils or dusts and sprays and spray solutions are usually not diluted with further inert substances before application. The required metering proportions of the mixture can be varied depending on external conditions such as temperature, humidity and the nature of the herbicide used and the like.

The following examples illustrate the invention. A. Formulation example a) One dust is obtained by mixing 10 parts by weight of a combination of the active substances according to the invention and 90 parts by weight of talc as inert substance and grinding this mixture with a hammer mill. b) One part wettable powder which can be easily dispersed in water 5 parts by weight of the combination of active substances, 64 parts by weight of quartz containing kaolin as inactive substance, 10 parts by weight of potassium lignin sulfonate and oleoyl as wetting and dispersing agent. Obtained by mixing 1 part by weight of sodium methyl taurate and grinding the mixture on a pin disk mill. c) combining 20 parts by weight of alkylphenol polyglycol ether easy one dispersant concentrates that can be dispersed in the active substance in water ^[(R) Triton ^((R) Triton) × 20
7] 6 parts by weight, 3 parts by weight of isotridecanol polyglycol ether (8 units of EO) and paraffinic mineral oil (boiling range, for example, up to about 255 to 277 ° C.)
It is obtained by mixing with 71 parts by weight and grinding this mixture in a ball mill to a fineness of less than 5 microns. d) One emulsion is obtained from 15 parts by weight of the active substance combination, 75 parts by weight of cyclohexane as solvent and 10 parts by weight of oxyethylated nonylphenol as emulsifier. e) Water-dispersible granules are mixed with 75 parts by weight of active substance, 10 parts by weight of calcium lignin sulfonate, 10 parts by weight of sodium lauryl sulfate, 5 parts by weight of polyvinyl alcohol, 3 parts by weight of kaolin, and 7 parts by weight of kaolin. It is obtained by grinding and spraying the powder in a fluidized bed onto water as the granulating liquid. f) Water-dispersible granules are also a combination of active substances 25 parts by weight 2,2'-dinaphthylmethane-6,6'-disulfonate 5 parts by weight Sodium oleoylmethyl taurate 2 parts by weight Polyvinyl alcohol 1 part by weight 17 parts by weight of calcium carbonate and 50 parts by weight of water are obtained by homogenizing and premilling in a colloid mill and spraying the resulting suspension in a spray tower with a single substance nozzle and drying. Example of biological test 1. Effects on Weeds in Pre-emergence Treatment Monocotyledonous and dicotyledonous weed plant seeds or rhizome fragments are planted and covered with sandy loamy soil in plastic pots 9 cm in diameter. The weeds that appear in rice cultivation are cultivated in submerged soil, filling the pot with water either to the surface of the soil or to a few millimeters above the surface of the soil. A combination of the active substances according to the invention formulated in the form of a wettable powder or an emulsion and the corresponding active substances formulated in parallel tests in water, corresponding to 300 to 600 l / ha It is applied as an aqueous suspension or emulsion in various application rates to the surface of the soil cover. When applied in rice cultivation, the active substance formulation is poured into irrigation water. After treatment, the pots are placed in a greenhouse and kept under conditions suitable for weed growth. After germination of the test plants, a visual assessment of the phytotoxicity to the plants and / or germination was carried out after a test period of 3 to 4 weeks by comparison with untreated controls. The herbicide according to the present invention exhibits an excellent preemergence herbicidal effect on a wide range of grasses and other weeds. In all cases, there was a difference between the calculated and measured effects in the combination. The calculated, theoretically expected degree of efficacy of one combination is calculated by the SR Colby formula: "Calculation of synergistic and antagonistic response of herbicidal combinations.
nergistic and antagonistic responses of herbicideC
ombinations, Weeds 15 (1967) 20-22). For two combinations, the above equation is:

[Equation 1] And therefore in the case of a combination of three herbicidally active substances:

[Equation 2] In the above formula, X = x is the degree of damage by the herbicide A at an application rate of x kg / ha (%); Y = is the degree of damage by the herbicide B at an application rate of y kg / ha (%); Z
= Z is the degree of damage (%) by one more herbicide B at an application rate of z kg / ha; E = x + y (or z)
It is the expected degree of damage by herbicide A + B (or B) at kg / ha. If the actual degree of damage is greater than that predicted by the calculation, then the action of the combination is more than additive, ie there is a synergistic effect. 2. Actions on weeds in post-emergence treatment: Seed or rhizome fragments of monocotyledonous and dicotyledonous weed plants are planted in sandy loamy soil in plastic pots, covered with soil and grown well in the greenhouse. Cultivate under conditions. The weeds appearing in rice cultivation are cultivated in pots filled with water up to 2 cm above the soil surface and allowed to grow for the duration of the test. Three weeks after sowing, the test plants are treated at the 3-leaf stage or when they reach a height of 3-5 cm (1-1.2 leaf stage). Combinations of the active substances according to the invention formulated in the form of wettable powders or emulsions and in parallel tests the corresponding formulated individual active substances are converted to 300 to 600 l / l.
The effect of the formulation was untreated after spraying on the green parts of the plants at different application rates with a water usage corresponding to ha and leaving the test plants in the greenhouse under optimal growth conditions for about 3 to 4 weeks. It is evaluated visually compared to the control. In the case of the weeds that emerge in rice production, the active substances are also added directly to the irrigation water (application method similar to so-called granulation) or sprayed on plants and irrigation water. The compositions according to the invention also show excellent herbicidal activity against a wide range of economically important grass and dicotyledon weeds even in post-emergence treatment. The action of the composition according to the invention is synergistic according to Colby's analysis. Cyperus serotin of the combination of active substances according to the invention
The herbicidal effect against us) is clear from Table 1. Table 1 Herbicidal effect Application rate Used individually and when used with Colby Value 1. 2. 3. 1. 2. 3. 1. 2. 3. A1 + B16 15 2.5 45 0 50 45 A1 + B16 + B22 15 2.5 150 45 0 20 62 56 15 2.5 200 45 0 5 61 48 A1 + B16 + B2 15 2.5 120 45 0 6 62 48 15 2.5 160 45 0 5 56 48 A1 + B16 + B23 15 2.5 50 45 0 0 61 45 15 2.5 75 45 0 22 68 57 A1 + B12 + B22 15 1.25 150 45 4 20 69 58 15 1.25 200 45 4 5 67 50 A1 + B12 + B2 15 1.25 120 45 4 6 65 50 A1 + B12 + B2 15 2.5 120 45 14 6 60 56 15 2.5 160 45 14 5 60 55 A1 + B12 + B3 15 1.25 250 45 4 39 79 68 15 1.25 350 45 4 77 76 88 A1 + B13 15 0.5 45 4 50 47 15 1 45 0 35 45 A1 + B13 + B22 15 1 200 45 0 5 67 48 A1 + B13 + B2 15 0.5 120 45 4 6 57 50 15 0.5 160 45 4 5 70 50 A1 + B13 + B2 15 1 120 45 0 6 71 48 15 1 160 45 0 5 61 48 A1 + B13 + B3 15 0.5 250 45 4 39 79 68 A1 + B13 + B23 15 0.5 50 45 4 0 52 47 Herbicidal effect Application rate Used individually Used together When using Corby When using 1. 2. 3. 1. 2. 3. 1. 2. 3. A1 + B13 + B23 15 1 50 45 0 0 61 45 15 1 75 45 0 22 58 57 A1 + B10 15 450 45 26 67 59 A1 + B10 + B22 15 450 150 45 26 20 67 67 15 450 200 45 26 5 72 61 A1 + B10 + B22 15 900 200 45 63 5 72 81 A1 + B10 + B2 15 450 120 45 26 6 68 62 15 450 160 45 26 5 68 61 A1 + B10 + B23 15 450 50 45 26 0 72 59 A1 + B10 + B23 15 900 50 45 63 0 82 80 A1 + B22 15 150 45 20 80 56 15 200 45 5 80 48 A1 + B2 15 120 45 6 71 48 15 160 45 5 75 48 A1 + B3 15 250 45 39 87 66 15 350 45 77 89 87 A1 + B23 15 50 45 0 75 45 15 75 45 22 75 57 Not Treatment control 0 0 0

─────────────────────────────────────────────────── ───

[Procedure amendment]

[Submission date] July 6, 1993

[Procedure Amendment 1]

[Document name to be amended] Statement

[Correction target item name] Full text

[Correction method] Change

[Correction content]

[Document name] Statement

Title: Herbicide composition

[Claims]

[Chemical 1] (In the above formula, R ¹ is halogen, (C ₁ -C ₄ ) -alkoxy, (C ₁
-C ₄₎ - _{alkyl, (C} 1 -C ₄₎ - haloalkyl,
-NO _2, -CN, or ^{_{S (O) n R 10;}} R 2
And R ³ are independently of each other hydrogen, halogen, (C _1-
C ₄₎ - _{alkyl, (C} 1 -C ₄₎ - alkoxy, (C
₁ -C ₄₎ - _{haloalkoxy, (C} 1 C ₄₎ - _{haloalkyl, -CN, -NO 2, -S (} O) m -R 11, -N
R ¹² R ^13, it is ^{-NR 14 -CO-R 15; R} 4
Is _{hydrogen, (C} 1 -C ₄₎ - alkyl, or -CO-O-
(C ₁ -C ₄ ) -alkyl; R ⁵ , R ⁶ , R ⁷ ,
R ⁸ and R ⁹ are independently of each other hydrogen or (C ₁ -C
₄₎ - alkyl, or ^{-CO-R 6; R 10} is _(C 1 -C ₄₎ - _{alkyl, (C} 1 -C ₄₎ - haloalkyl or _(C 1 -C ₄₎ - ^{alkoxy; R 11}
And _(C 1 -C ₄₎ - _{alkyl, (C} 1 -C ₄₎ - haloalkyl, phenyl, benzyl, or ^-NR 17 ^{R 18; R 12} and ^{R 13} are each independently of the other hydrogen or _(C 1 -C ₄ ) -alkyl; R ¹⁴ is hydrogen or (C ₁ -C ₄ ) -alkyl; R ¹⁵ is (C ₁ -C
₄ ) -alkyl; R ¹⁶ is hydrogen, (C ₁ -C ₄ ).
-Alkyl, (C ₁ -C ₄ ) -haloalkyl or (C
₁ -C ₄₎ - ^{alkoxy; R 17} and ^{R l8} are each independently of the other hydrogen or _(C 1 -C ₄₎ - alkyl and n and m independently of one another are 0, 1 or 2
An effective amount of a compound represented by the formula (1) or a salt thereof (compound of type A) is the following compound B1) butachlor (b)
utachlor), N (butoxymethyl) -2-chloro-N- (2,6-diethylphenyl) -acetamide

[Chemical 2] B2) Pretilachlor
r), N- (2-propoxyethyl) -2-chloro-N
-(2,6-Diethyl-phenyl) -acetamide

[Chemical 3] B3) Mefenacet, 2-
(1,3-benzothiazol-2-yloxy) -N-
Methyl-acetanilide

[Chemical 4] B4) Esprocarb, S-benzyl N-ethyl- (1,2-dimethyl-propyl)
-Thiocarbamate

[Chemical 5] B5) butenachlor,
(Z) -N-but-2-enyloxymethyl-2-chloro-2 ', 6'-diethylacetanilide, KH-2
18

[Chemical 6] B6) Molinate, N- (ethylthio-carbonyl) -azepane

[Chemical 7] B7) thiobencarb,
(Benchiocarb) S-4
-Chlorobenzyl N, N-diethylthiocarbamate

[Chemical 8] B8) dimepiperate
(MY-93), N- (2-phenyl-prop-2-
Ilthiocarbonyl) piperidine

[Chemical 9] B9) NSK-850, α-chloro-N- (3-methoxy-2-thienyl) -methyl-2 ′, 6′-dimethylacetanilide

[Chemical 10] B10) Pyrazolinate
e), 4- (2,4-dichlorobenzoyl) -1,3-
Dimethylpyrazol-5-yltoluene-4-sulfonate

[Chemical 11] B11) Naproanilide
e), 2- (2-naphthyloxy) propionanilide

[Chemical 12] B12) Bensulfuron-methyl (bensulfur)
on-methyl), α- (4,6-dimethoxypyrimidin-2-yl-carbamoyl-sulfamoyl)-
O-toluic acid

[Chemical 13] B13) Pyrazosulfuron-ethyl (pyrazosu)
lfuron-ethyl), 5- (4,6-dimethoxypyrimidin-2-yl (carbamoylsulfamoyl) -1-methylpyrazole-4-carboxylic acid

[Chemical 14] B14) Cinosulfuron
n), 3- (4,6-dimethoxy-1,3,5-triazin-2-yl-1- [2- (2-methoxyethoxy)
-Phenylsulfonyl] urea

[Chemical 15] B15) Imazosulfuron
n), N- (2-chloro-imidaza [1,2-α] pyridin-3-yl-sulfonyl) -N ′-(4,6-dimethoxy-2-pyrimidinyl) -urea (TH-913, European Patent Example 1 of No. 0,238,070)

[Chemical 16] B16) H1,3- (4,6-dimethoxypyridine-2)
-Yl) -1- (2-ethoxyphenoxysulfonyl)
Urea, (see German Patent Application P3816704.2, European Patent Application Publication No. 0,342,569).

[Chemical 17] B17) Pyrazoxyphen
n), 2- [4- (2,4-dichloro-benzoyl)-
1,3-Dimethylpyrazol-5-yloxy] -acetophenone

[Chemical 18] B18) Penzofenap
(MY71), 2- [4- (2,4-dichloro-m-toluoyl) -1,3-dimethylpyrazol-5-yloxy] -4'-methylacetophenone

[Chemical 19] B19) dithiopyr, 5,
5'-Dimethyl 2-difluoromethyl-4-isobutyl-6-trifluoromethylpyridine-3,5-dicarbothioate

[Chemical 20] B20) HW52, 2 ′, 3′-dichloro-4-ethoxymethoxybenzanilide (see JP-A-60-42312)

[Chemical 21] B21) Pyributical
b), O-3-tert-butylphenyl 6-methoxy-
2-pyridyl (methyl) thiocarbamate

[Chemical formula 22] B22) anilofos, 4'-chloro-2-dimethoxyphosphinothioylthio-N-isopropylacetanilide

[Chemical formula 23] B23) CH900, 1- (diethylcarbamoyl)-
3- (2,4,6-trimethylphenylsulfonyl)-
1,2,4-triazole

[Chemical formula 24] And B24) daimuron, 1- (1-
Methyl-1-phenylethyl) -3-p-tolyl-urea

[Chemical 25] At least one compound B selected from the group consisting of
A herbicidal composition containing (B-type compound) in combination (provided that an effective amount of compound A is B1 to B4, B6 to B)
8, B17 to B20 and B22 except for the composition containing it in combination with only one compound B selected from the group consisting of).

Detailed Description of the Invention

TECHNICAL FIELD The present invention relates to a herbicidal composition for controlling weeds in cultivated crops, especially rice cultivation.

2. Description of the Related Art WO91 / 05469 and WO91 /
05470 discloses combinations of herbicidal compositions and active substances which can be used for controlling unwanted plants in rice production. These herbicidal compositions include
Also included are synergistically effective mixtures to control a wide range of monocotyledonous and dicotyledonous weeds in rice cultivation.

However, in rice cultivation in Japan and Southeast Asia, weeds that are not sufficiently controlled even when such a combination is used are known. (Sagittaria spp.), Kuroguai (E
leOcaris kuroguwai) and broad-leaved species are also included.

Surprisingly, the present inventors have found that when used together in biological greenhouse experiments with a wide range of herbicidally active substances, a wide variety of weeds were identified. A new synergistically effective combination of active substances has been found, which has a very excellent action and is extremely tolerant to rice. They are superior in their range of action and effect to known herbicides and herbicidal compositions and can be used in low dosages. Another advantage of these novel combinations is their duration of action, which lasts for several weeks and thus saves further application of herbicides to newly germinated weeds. 1
The fact that one application is sufficient for weed growth makes the second application unnecessary. The present invention provides compounds of formula I or salts thereof (compounds of type A):

[Chemical formula 26] (In the above formula, R ¹ is halogen, (C ₁ -C ₄ ) -alkoxy, (C ₁ -C ₄ ))-alkyl, (C ₁ -C ₄ ) -haloalkyl, —NO ₂ , —CN or S ( O) _n R ¹⁰
R ² and R ³ are independently of each other hydrogen, halogen, (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -alkoxy, (C ₁ -C ₄ ) -haloalkoxy, (( C ₁ −
C ₄₎ - _{haloalkyl, -CN, -NO 2, -S (} O)
_{^{m -R 11, -NR 12 R 13}} , -NR 14 -CO-R
It is ^{15; R 4} is _{hydrogen, (C} 1 -C ₄₎ - alkyl, or _{-CO-O- (C 1 -C 4} ) - is alkyl; R
^{5, R 6, R 7,} R 8 and ^{R 8} are each independently of the other hydrogen or _(C 1 -C ₄₎ - alkyl, or ^{-CO-R 6; R 10} is _(C 1 -C ₄₎ - alkyl , (C ₁ -C
₄ ) -haloalkyl or (C ₁ -C ₄ ) -alkoxy; R ¹¹ is (C ₁ -C ₄ ) -alkyl, (C _1- ).
C ₄₎ - haloalkyl, phenyl, benzyl or -N
R ¹⁷ R ¹⁶ ; R ¹² and R ¹³ are independently of each other hydrogen or (C ₁ -C ₄ ) -alkyl; R
¹⁴ is hydrogen or (C ₁ -C ₄ ) -alkyl; R
¹⁵ is (C ₁ -C ₄ ) -alkyl; R ¹⁶ is hydrogen, (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -haloalkyl or (C ₁ -C ₄ ) -alkoxy ; R
¹⁷ and R ¹⁸ are independently of each other hydrogen or (C _1-
C ₄ ) -alkyl and n and m independently of each other are 0, 1 or 2) or an effective amount of a salt thereof (compound of type A), a compound B1) butachlor, N (butoxymethyl) -2-chloro-N- (2,6-diethylphenyl-acetamide

[Chemical 27] B2) Pretilachlor, N- (2-propoxyethyl) -2-chloro-N- (2,6-diethyl-phenyl) -acetamide

[Chemical 28] B3) Mefenacet, 2- (1,3-benzothiazol-2-yloxy) -N-methyl-acetanilide

[Chemical 29] B4) Esplocarb, S-benzyl N-ethyl-
(1,2-Dimethyl-propyl) -thiocarbamate

[Chemical 30] B5) Butenachlor, (Z) -N-but-2-enyloxymethyl-2-chloro-2 ′, 6′-diethylacetanilide, KH-218

[Chemical 31] B6) Molinate, N- (ethylthio-carbonyl-azepane

[Chemical 32] B7) Thioben curve, (bench curve), S-4-
Chlorobenzyl N, N-diethylthiocarbamate

[Chemical 33] B8) Dimepiperate (MY-93), N- (2-phenyl-prop-2-ylthiocarbonyl) piperidine

[Chemical 34] B9) NSK-850, α-chloro-N- (3-methoxy-2-thienyl) -methyl 2 ′, 6′-dimethylacetanilide

[Chemical 35] B10) Pyrazolinate, 4- (2,4-dichlorobenzoyl) -1,3-dimethylpyrazol-5-yltoluene-4-sulfonate

[Chemical 36] B11) Naproanilide, 2- (2-naphthyl) propionanilide

[Chemical 37] B12) Bensulfuron-methyl, α- (4,6-dimethoxypyrimidin-2-yl-carbamoyl-sulfamoyl) -O-toluic acid

[Chemical 38] B13) Pyrazosulfuron-ethyl, 5- (4,6-dimethoxypyrimidin-2-yl (carbamoylsulfamoyl) -1-methylpyrazole-4-carboxylic acid

[Chemical Formula 39] B14) Cinosulfuron, 3- (4,6-dimethoxy-)
1,3,5-triazin-2-yl-1- [2- (2-
Methoxyethoxy) -phenylsulfonyl] urea

[Chemical 40] B15) Imazosulfuron, N- (2-chloro-imidaza [1,2-α] pyridin-3-yl-sulfonyl)-
N '-(4,6-dimethoxy-2-pyrimidinyl) -urea (TH-913, European Patent No. 0,238,07
No. 0 example 1)

[Chemical 41] B16) H1,3- (4,6-dimethoxypyridine-2)
-Yl) -1- (2-ethoxyphenoxysulfonyl)
Urea, (see German Patent Application P3816704.2, European Patent Application Publication No. 0,342,569).

[Chemical 42] B17) Pyrazoxyphene, 2- [4- (2,4-dichloro-benzoyl) -1,3-dimethylpyrazole-5
-Yloxy] -acetophenone

[Chemical 43] B18) Benzophenap (MY71), 2- [4-
(2,4-Dichloro-m-toluoyl-1,3-dimethylpyrazol-5-yloxy] -4'-methylacetophenone

[Chemical 44] B19) Dithiopeel, 5,5'-dimethyl 2-difluoromethyl-4-isobutyl-6-trifluoromethylpyridine-3,5-dicarbothioate

[Chemical formula 45] B20) HW52, 2 ', 3'-dichloro-4-ethoxymethoxybenzanilide (JP-A-60-42)
(See No. 312)

[Chemical formula 46] B21) Pyributicarb, O-3-tert-butylphenyl 6-methoxy-2-pyridyl (methyl) thiocarbamate

[Chemical 47] B22) Anilophos, 4'-chloro-2-dimethoxyhoffinothioylthio-N-isopropylacetanilide

[Chemical 48] B23) CH900, 1- (diethylcarbamoyl)-
3- (2,4,6-trimethylphenylsulfonyl)-
1,2,4-triazole

[Chemical 49] And B24) Daimlon, 1- (1-methyl-1-phenylethyl) -3-p-tolyl-urea

[Chemical 50] At least one compound B selected from the group consisting of
A herbicidal composition containing (B-type compound) in combination (provided that an effective amount of compound A is B1 to B4, B6 to B)
8, B17 to B20 and B22, except for the composition containing in combination with only one compound B selected from the group). All of the above compounds are listed in "The Pesticide Manual, 9th Edition, published by The Crop Protection Council, 1991 (The Pesticide Manual, 9th
Edition, Brit. Crop. Counci
1, 1991) ", but B1 as described in all the patent application specifications mentioned therein.
5, except B16 and B20. Compound B23 is 19
Report 923 Brighton Crop Conservation Conference Weed Section Report 923
-928 page (Brighton Crop Prot.
Conf. Weeds, 1991, p923-928)
Known from. Particularly interesting herbicidal compositions according to the invention are those of the formula I in which R ¹ is fluorine, chlorine, bromine,
Iodine, methoxy, nitro, cyano or -S (O) _n
R ¹⁰ ; R ² and R ³ independently of one another are hydrogen,
Fluorine, chlorine, bromine, iodine, methyl, methoxy, trifluoromethoxy, cyano, nitro, _{^{trifluoromethyl, -SO 2 R 11, NR 12}} R 13, -N (CH 3)
^{-CO-R 14} or _{-CO-O- (C 1 -C 4} ) - alkyl and ^{R 4, R 5, R 6} , R 7, R 8 and ^{R 9} are located in each independently of the other hydrogen or methyl And a herbicidal composition containing a compound represented by the above formula I or a salt thereof in which R ¹⁰ , R ¹¹ , R ¹² , R ¹³ R ¹⁴ and n have the above-mentioned meanings. Particularly preferred herbicidal compositions according to the invention are those in which R ² and R ³ independently of one another are hydrogen, fluorine, chlorine, bromine, N (CH ₃ ) ₂ ,
Methoxy, _{nitro, -SO 2 CH 3, SO 2} CH 2 C
_l, an -SO 2 N _{(CH 3) 2} or trifluoromethyl and n is 2, and ^{R 1, R 4, R 5} ,
R ⁶ , R ⁷ , R ⁸ and R ⁹ contain the compound represented by the above formula I having the above-mentioned meanings. The compounds of formula I exist in various tautomeric structures (keto-enol type tautomerism) and have a highly acidic hydrogen atom on the methine group between the three carbonyl groups. , It can be replaced by agriculturally suitable cations. The salts obtained are generally metal salts, in particular alkali metal salts, alkaline earth metal salts, optionally substituted or unsubstituted ammonium salts, sulfonium salts or phosphonium salts, wherein the substituents are aliphatic or aromatic. Can be a tribe. Suitable bases for the preparation of the salts according to the invention are, for example, alkali metal carbonates such as potassium carbonate, alkali metal hydroxides and alkaline earth metal hydroxides, ammonia or ethanolamine. The alkyl group is
It is intended to mean a group having the indicated number of carbons. These groups may be linear or branched. Examples of the most frequently used groups are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl. Halogen shall mean fluorine, chlorine, bromine or iodine. Haloalkyl groups may be mono- or poly-substituted by halogen, ie they may be perhalogenated.
An example of a particularly suitable compound of formula I in a herbicidal mixture according to the invention is 2- (2-chloro-4-methylsulfonylbenzoyl)
-1,3-Cyclohexanedione (A1) 2- (2-nitrobenzoyl) -4,4-dimethyl-
1,3-Cyclohexanedione (A2) and 2- (2-nitrobenzoyl) -5,5-dimethyl-
It is 1,3-cyclohexanedione (A3). The 2-benzoylcyclohexanedione derivative of formula I is described, for example, in the above-mentioned European Patent Application Publication No. 0,
137,963, 0,186,118, 0,274,634 and 0,298,680 and U.S. Pat. No. 4,780,127, or they are It can be produced by the methods described in these publications. The following are mentioned by way of specific examples of mixtures of active substances according to the invention, without being restricted to these: A ₁ + Bensulfuron-methyl A ₁ + 〃 〃 + Mefuenasetto (mefenacet) _A 1 + undefined undefined + butachlor (butachlor) _A 1 + undefined undefined + Esupuro curve (esprocarb) _A 1 + undefined undefined + Purechirakuroru (pretilaChlor) _A 1 + undefined undefined + molinate (molinate) _A 1 + undefined undefined + Butenakuroru (butenachlor) _A 1 + undefined undefined + bench A curve (benthiocarb) _A 1 + undefined undefined + dimepiperate (dimepiperate) _A 1 + undefined undefined + NSIY-850 _A 1 + undefined undefined + Jichiopi (Dithiopyr) _A 1 + undefined undefined + NW 52 _A 1 + undefined undefined + Piribuchikabu (pyributicarb) _A 1 + undefined undefined + anilofos (anilofos) _A 1 + undefined undefined + CN The following mixtures containing up to 900 4 components are also possible Yes,
A ₁ + bensulfuron shows a herbicidal effect which is superior in biological experiments - methyl + dymron (daimuron) _A 1 + undefined undefined + Mefuenasetto + dymron A ₁ + undefined undefined + butachlor + dymron A ₁ + undefined undefined + Esupuro curve + dymron A ₁ + undefined undefined + pretilachlor + dymron A ₁ + undefined undefined + molinate + dymron A ₁ + undefined undefined + Butenakuroru + dymron A ₁ + undefined undefined + thiobencarb + dymron A ₁ + undefined undefined + dimepiperate + dymron A ₁ + undefined undefined + NSK 850Tasu dymron A ₁ + undefined undefined + Jichiopiru + dymron A ₁ + undefined undefined + NW 52Tasu daimuron A ₁ + undefined undefined + Piribuchikabu + dymron A ₁ + undefined undefined + anilofos + dymron A ₁ + undefined undefined + CH 900+ Daimuro In these combinations listed, use of daimuron is very advantageous in two respects: that is, in contrast, dymron is Cyperus compound (Cyperus
spp. ) And grass weeds, and on the other hand, dimuron also acts as a safener for crop plant rice and is evoked by herbicides or other active substances such as sulfonylurea derivatives. Reduce potential phytotoxicity. However, the above-mentioned mixture additionally contains compound A1 as active substance A2.
Or it can be further modified by substituting by A3. Similarly, in the mixtures listed in the table above,
The active substance B12 = bensulfuron-methyl can be replaced by the following different sulphonylureas: B13,
Pyrazosulfuron-ethyl or B14, Cinosulfuron or B15, Imazosulfuron (TH913) or B16, H1 or a combination of two sulphonylureas, for example B13 + B16. Similarly, one of the following herbicides can be admixed into a mixture of three or four instead of the sulfonylurea derivative; B10, pyrazolinate B17, pyrazoxifene B18, benzophenap B11, naproanilide. This results in a number of possibilities for combining 3 or 4 herbicidal active substances and using them together for controlling weeds in rice. The herbicidal compositions (combinations) according to the invention show a significant herbicidal action against a wide range of economically important monocotyledonous and dicotyledonous harmful plants. These active substances also germinate from rhizomes, root fragments or other perennial organs,
It also works effectively on perennial weeds that are difficult to control. In this connection, it does not matter whether the active substance is applied before sowing, before germination or after germination. In particular, some representative examples of monocotyledonous and dicotyledonous weed groups that may be controlled by the compositions according to the invention may be mentioned, but this list is not intended to be limited to a particular species. Examples of vegetative species against which the composition according to the present invention effectively acts include, among monocotyledons, Echinochloa, perennial, Cyperus spp., And perennial Cyperaceae, among perennial species. Is. The combination of active substances according to the invention is, for example, Urikawa (Sagittari).
a), Omodaka (Alisma), Yellow cypress (Rot)
ala), eel (Monochoria), harii (Eleocharis), firefly (Sirpu)
s), Cyperus, etc. have a significant effect on the control of weeds that may be found under certain conditions of rice cultivation. When the herbicidal composition according to the invention is applied to the surface of the soil before germination, the seedlings of the weeds are completely arrested or the weeds grow until they reach the cotyledon stage. Their growth stopped and eventually 3
After 4 to 4 weeks, they die completely. If compositions of these active substances are applied to the green parts of the plants after germination, the growth likewise stops dramatically very shortly after treatment. Since weed plants remain in the growth stage at the time of application or they die rapidly to a greater or lesser extent after a certain period of time, the competition of weeds harmful to cultivated plants in this way is novel according to the invention. By using such a composition, it can be eliminated very early and persistently. The composition according to the present invention shows an excellent herbicidal action against monocotyledonous and dicotyledonous weeds, but the cultivated rice plant,
No illness or negligible. For these reasons, the compositions of the present invention are highly suitable for the selective control of unwanted plants in rice cultivation. The active substance combinations according to the invention make it possible to achieve herbicidal effects which far exceed those expected on the basis of the effects of the individual components. These increased effects considerably reduce the proportion of individual active substances dosed. The combination of herbicides also improves their long-lasting action or makes them act more rapidly. Such properties are of great advantage to the user when actually controlling weeds. They enable weeds to be controlled more economically, less labor-intensive and more persistent, thus allowing higher yields to be harvested on standing cultivated plants. Furthermore, is there a significant detoxifying or detoxifying effect in the series of active substance combinations, i.e. the reduction of the phytotoxic secondary effects of the active substances used, for example in cultivated plants such as rice? Or it was found to be completely avoided. The proportions in which the various components are mixed can be varied within a very wide range. Their proportions depend in particular on the mixed components used, the developmental stage of the weeds, the range of the weeds and the climatic conditions. The active substances according to the invention can be present in the form of a mixed preparation of the two components, which are then diluted in water in the customary manner or applied in the form of granules. Alternatively, it may be prepared as a so-called tank mix by combining the separately formulated ingredients together and diluting with water. The compounds (combinations) can be formulated in various ways depending on the general biological and / or chemical-physical parameters. Suitable possible formulations include: Wettable powders (WP), emulsions (emulsifiable concentrates).
(EC), aqueous solutions (SL), emulsions (EW) such as oil-in-water and water-in-oil emulsions, spraying solutions or emulsions, oil- or water-based dispersions,
Suspoemulsions, dusts (DP), seed treatments, but especially soil or dusting granules or water-dispersible granules (WG), ULV formulations, microcapsules or waxes. These individual formulation forms are known in principle and are described, for example, in: Winnacker-Kuec.
Heller) “Chemische Tec
hnologie) "Volume 7 published by Hauser Company (C. Hau
ser Verlag, Muenchen) 4th edition 19
1986; van Valk
Enburg) "Pesticide Formulation" (Pesticide)
Marcel Dekker NY, 2nd edition 19
72-73; "Spray Drying Handbook" edited by K. Martens.
Handbook, 3rd edition, published by Goodwin, Inc. in 1979 (G. Goodwin Ltd., London
n). Necessary formulation auxiliaries, such as necessary formulation auxiliaries such as inert substances, surfactants, solvents and other additives are likewise known and are described, for example, in the following documents: Watkins ( Watkins) “Powder Diluents and Carriers for Insecticides” (Handbook of Inse)
cticide Dust Diluents and
Carriers, 2nd edition, published by Darland Books, Inc. (Darland Books, Caldwell)
N. J. ); "Introduction to Clay Colloid Chemistry" by Hv Olphen.
to ClayColloid Chemistr
y) Second edition published by Willy & Sons (J. Wiley & Sons,
N. Y. ); Marsden, "Solvents Guide," 2nd Edition, Interscience, N .;
Y. 1950); McCutcheon
n's) "Detergent and Emulsifier Yearbook" (Deterge
nts and Emulsifiers Annua
ls) Published by MC Publishing Co. (MC Publ. Corps. R
idwood, N.N. J. ); Sisley and Wood co-edited (Sisley and Wood) “Encyclopedia of Surfactants (Encyclopedia of Surface)
Active Agents) Chemical Publishing Company 196
4 years (Chem. Publ. Co. Inc., N. et al.
Y. ); Schoenfeldt
By "Surface Active Ethylene Oxide Adducts" (Grenz
flaechenaktive Athelenox
idaddukte) Science Publishing Company, 1976 (Wis
s. Verlagsgesell. , Stuttgar
t); Winnacker
-Kuechler) Co-editing "Chemical Technology (Chemisc
he Technology, Volume 7, published by Hauser Company (C. Hauser Verlag Muenche)
n) Fourth edition 1986. Based on these formulations, other herbicides, other pesticidally active substances such as fungicides or insecticides, and also in combination with fertilizers and / or growth regulators are also produced, for example in the form of ready mixes or tank mixes. sell. Wettable powders are preparations which can be dispersed homogeneously in water and, in addition to the active substance, also wetting agents, for example polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols or fatty amines, alkanes.
Or an alkylbenzene sulfonate, and a dispersant,
It contains, for example, sodium glycine sulfonate, sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, sodium dibutylnaphthalene sulfonate or even sodium oleylmethyl taurate, together with diluents or inert substances. Emulsions (emulsifiable concentrates) are prepared, for example, by adding one or more emulsifiers to the active substance in an organic solvent such as butanol, cyclohexane, dimethylformamide, xylene, or else a high-boiling aromatic or hydrocarbon. It can be manufactured by dissolving. Emulsifiers which can be used are, for example: calcium salts of alkylaryl sulphonic acids such as calcium dodecylbenzene sulphonate, or fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide / ethylene oxide condensation products, Nonionic emulsifiers such as alkyl polyethers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters or polyoxyethylene sorbitan esters. Dusts are obtained by grinding the active substance with finely divided solid substances, for example talc, for example kaolin, bentonite and naturally occurring clays such as pyrophyllite or diatomaceous earth. Granules are prepared by spraying the active substance on adsorptive granular inert substances or by adhering the active substance concentrate onto the surface of a carrier such as sand, kaolinite or granulated inert substances, for example polyvinyl alcohol, polyalcohol. It may be produced by coating with sodium acrylate, or else mineral oil. Suitable active substances can be granulated in the manner customary for the production of fertilizer granules, if desired in admixture with fertilizers. In general, the pesticide formulations according to the invention contain the active substances A and B in an amount of 0.1 to 99.
%, Especially 2 to 95% by weight. These formulations can vary with regard to the concentrations of active substances A and B. The concentration of the active substance in the wettable powder is, for example, about 10 to 9
5% by weight, the rest up to 100% consisting of the usual formulation ingredients. In the case of emulsions, the active substance concentration may be about 1 to 85% by weight, preferably 5 to 80% by weight.
Formulations in the form of powders contain from about 1 to 25% by weight, often from 5 to 20% by weight of the active substance, the spray solution being about 0.2 to 25% by weight, preferably 2 to 20% by weight. % Active substance. In the case of granules, for example water-dispersible granules, the active substance content depends in part on whether the active substance is a liquid or a solid and what granulating aids and fillers are used. It depends. Generally, water dispersible granules are 5 to 90% by weight.
And the spreading granules contain 1 to 50% by weight, preferably 2 to 25% by weight, of the active substance. Furthermore,
The active substance formulations mentioned above optionally comprise in each case an adhesive, wetting agent, dispersant, emulsifier, penetrant, solvent, filler or carrier. The formulations, which are present in the commercially available forms, are optionally diluted in use in the customary manner, for example with water in the case of wettable powders, emulsions, dispersions and water-dispersible granules. Dusts and soils or dusts and sprays and spray solutions are usually not diluted with further inert substances before application. The required metering proportions of the mixture can be varied depending on external conditions such as temperature, humidity and the nature of the herbicide used and the like.

The following examples illustrate the invention. A. Formulation example a) One dust is obtained by mixing 10 parts by weight of a combination of the active substances according to the invention and 90 parts by weight of talc as inert substance and grinding this mixture with a hammer mill. b) One part wettable powder which can be easily dispersed in water 5 parts by weight of the combination of active substances, 64 parts by weight of quartz containing kaolin as inactive substance, 10 parts by weight of potassium lignin sulfonate and oleoyl as wetting and dispersing agent. Obtained by mixing 1 part by weight of sodium methyl taurate and grinding the mixture on a pin disk mill. c) One dispersible concentrate which can be easily dispersed in water is combined with 20 parts by weight of the active substance combination alkylphenol polyglycol ether [ ^(R) Triton ( ^(R) Trito] ^).
n) × 207] 6 parts by weight, 3 parts by weight of isotridecanol polyglycol ether (8 units of EO) and 71 parts by weight of paraffinic mineral oil (boiling range, eg up to about 255 to 277 ° C.), and this mixture. Is obtained by pulverizing with a pole mill to a fineness of 5 microns or less. d) One emulsion is obtained from 15 parts by weight of the active substance combination, 75 parts by weight of cyclohexane as solvent and 10 parts by weight of oxyethylated nonylphenol as emulsifier. e) Water-dispersible granules are mixed with 75 parts by weight of active substance, 10 parts by weight of calcium lignin sulfonate, 10 parts by weight of sodium lauryl sulfate, 5 parts by weight of polyvinyl alcohol, 3 parts by weight of kaolin, and 7 parts by weight of kaolin. It is obtained by grinding and spraying the powder in a fluidized bed onto water as the granulating liquid. f) Water-dispersible granules are also a combination of active substances 25 parts by weight 2,2'-dinaphthylmethane-6,6'-disulfonate 5 parts by weight Sodium oleoylmethyl taurate 2 parts by weight Polyvinyl alcohol 1 part by weight It is also obtained by homogenizing and premilling 17 parts by weight of calcium carbonate and 50 parts by weight of water in a colloid mill and spraying the resulting suspension with a single substance nozzle in a spray tower and drying. Example of biological test 1. Effects on Weeds in Pre-emergence Treatment Monocotyledonous and dicotyledonous weed plant seeds or rhizome fragments are planted and covered with sandy loamy soil in plastic pots 9 cm in diameter. The weeds that appear in rice cultivation are cultivated in submerged soil, filling the pot with water either to the surface of the soil or to a few millimeters above the surface of the soil. A combination of the active substances according to the invention formulated in the form of a wettable powder or an emulsion and the corresponding active substances formulated in parallel tests in water, corresponding to 300 to 600 l / ha It is applied as an aqueous suspension or emulsion in various application rates to the surface of the soil cover. When applied in rice cultivation, the active substance formulation is poured into irrigation water. After treatment, the pots are placed in a greenhouse and kept under conditions suitable for weed growth. After germination of the test plants, a visual assessment of the phytotoxicity to the plants and / or germination was carried out after a test period of 3 to 4 weeks by comparison with untreated controls. The herbicide according to the present invention exhibits an excellent preemergence herbicidal effect on a wide range of grasses and other weeds. In all cases, there was a difference between the calculated and measured effects in the combination. The calculated, theoretically expected degree of effectiveness of one combination is the formula of SR Colby:
"Calculation of synergistic and antagonistic responses of herbicidal combinations (Cal
calculation of synergistic a
nd antagonistic responses
of herbicide Combination
s, weeds 15 (1967) 20-22). For two combinations, the above equation is:

[Equation 1] And therefore in the case of a combination of three herbicidally active substances:

[Equation 2] In the above formula, X = x is the degree of damage (%) by herbicide A at an application rate of x kg / ha; Y = is the degree of damage (%) by herbicide B at an application rate of y kg / ha; Z = the degree of damage (%) by one more herbicide B at an application rate of z kg / ha; E = x + y (or z) herbicide A + at kg / ha
It is the expected degree of damage due to B (or B). If the actual degree of damage is greater than that predicted by the calculation, then the action of the combination is more than additive, ie there is a synergistic effect. 2. Actions on weeds in post-emergence treatment: Seed or rhizome fragments of monocotyledonous and dicotyledonous weed plants are planted in sandy loamy soil in plastic pots, covered with soil and grown well in the greenhouse. Cultivate under conditions. The weeds appearing in rice cultivation are cultivated in pots filled with water up to 2 cm above the soil surface and allowed to grow for the duration of the test. Three weeks after sowing, the test plants are treated at the 3-leaf stage or when they reach a height of 3-5 cm (1-1.2 leaf stage). Combinations of the active substances according to the invention formulated in the form of wettable powders or emulsions and in parallel tests the corresponding formulated individual active substances are converted to 300 to 600 l / l.
The effect of the formulation was untreated after spraying on the green parts of the plants at different application rates with a water usage corresponding to ha and leaving the test plants in the greenhouse under optimal growth conditions for about 3 to 4 weeks. It is evaluated visually compared to the control. In the case of the weeds that emerge in rice cultivation, the active substances are also added directly to the irrigation water (application method similar to so-called granulation treatment) or sprayed on plants and irrigation water. The compositions according to the invention also show excellent herbicidal activity against a wide range of economically important grass and dicotyledon weeds even in post-emergence treatment. The action of the composition according to the invention is synergistic according to Colby's analysis. Cyperus (Cyperus) of the active substance combinations according to the invention
The herbicidal effect against serotinus) is clear from Table 1.

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁵ Identification number Office reference number FI technical display location A01N 43/40 101 D 9159-4H 43/50 N 9159-4H 43/56 B 9159-4H 43 / 78 101 9159-4H 47/12 A 9159-4H 47/16 B 9159-4H 47/18 101 A 9159-4H 47/30 C 9159-4H 47/36 101 E 9159-4H 47/38 A 9159-4H ( 72) Inventor Hermann Boehringer, Federal Republic of Germany, Eppschyutine im Taunus, Eichenwake, 26 (72) Inventor Elwin Hacker, Federal Republic of Germany, Hochheim am Main, Margarethenstraße, 16

Claims (9)

[Claims] 1. Formula I (In the above formula, R ¹ is halogen, (C ₁ -C ₄ ) -alkoxy, (C ₁ -C ₄ ))
-Alkyl, (C ₁ -C ₄ ) -haloalkyl, -NO ₂ ,-
CN or S (O) _n R ¹⁰ ; R ² and R ³ are independently of each other hydrogen, halogen, (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -alkoxy, (C _1- C ₄ ) -haloalkoxy, (C ₁ -C ₄ ) -haloalkyl, —CN, —NO ₂ , —
S (O) _m -R ¹¹ , -NR ¹² R ¹³ , -NR ¹⁴ -CO-R ¹⁵ ; R ⁴ is hydrogen, (C ₁ -C ₄ )-
Alkyl or _{-CO -O- (C 1 -C 4)} - is ^{alkyl; R 5, R 6, R} 7, R 8 and R ⁹ are each independently of the other hydrogen or (C ₁ -C ₄₎ - alkyl or -CO-R ⁶ ; R ¹⁰ is (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -haloalkyl or (C ₁ -C ₄ ) -alkoxy; R ¹¹ and (C _1- C ₄ ) -alkyl, (C ₁ -C ₄ ) -haloalkyl, phenyl, benzyl or —NR ¹⁷ R ¹⁸ ; R ¹² and R ¹³ independently of one another are hydrogen or (C ₁ -C ₄ ) -alkyl. R ¹⁴ is hydrogen or (C ₁ -C ₄ ) -alkyl; R ¹⁵ is (C ₁ -C ₄ ) -alkyl; R ¹⁶ is hydrogen;
(C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -haloalkyl or (C ₁ -C ₄ ) -alkoxy; R ¹⁷ and R ¹⁸ independently of one another are hydrogen or (C ₁ -C _4). ) -Alkyl and n and m independently of each other are 0, 1 or 2) or an effective amount of a salt thereof (compound of type A), a compound B1) , N (butoxymethyl) -2-chloro-N- (2,6-diethylphenyl) -acetamide embedded image B2) Pretilachlor, N- (2-propoxyethyl) -2-chloro-N- (2,6-diethyl-
Phenyl) -acetamide B3) mefenacet, 2- (1,3-benzothiazol-2-yloxy) -N-methyl-acetanilide embedded image B4) Esprocarb (esprocarb), S-benzyl N
-Ethyl- (1,2-dimethyl-propyl) -thiocarbamate B5) Butenachlor, (Z) -N-but
-2-enyloxymethyl-2-chloro-2 ', 6'-diethylacetanilide, KH-218 B6) Molinate, N- (ethylthio-carbonyl) -azepane embedded image B7) thiobencarb, (benthiocarb) S-4-chlorobenzyl N, N-
Diethyl thiocarbamate [Chemical formula 8] B8) Dimepiperate (MY-9)
3), N- (2-phenyl-prop-2-ylthiocarbonyl) piperidine embedded image B9) NSK-850, α-chloro-N- (3-methoxy
-2-thienyl) -methyl-2 ', 6'-dimethylacetanilide B10) Pyrazolynate, 4- (2,4-
Dichlorobenzoyl) -1,3-dimethylpyrazole-5
-Illtoluene-4-sulfonate B11) Naproanilide, 2- (2-naphthyloxy) propionanilide embedded image B12) Bensulfuron-methy
l), α- (4,6-dimethoxypyrimidin-2-yl-
Carbamoyl-sulfamoyl) -O-toluic acid B13) Pyrazosulfuron-ethyl (pyrazosulfuron-e
thyl), 5- (4,6-dimethoxypyrimidin-2-yl (carbamoylsulfamoyl) -1-methylpyrazole
-4-carboxylic acid B14) Cinosulfuron, 3- (4,6-
Dimethoxy-1,3,5-triazin-2-yl-1-
[2- (2-methoxyethoxy) -phenylsulfonyl] urea B15) Imazosulfuron, N- (2-
Chloro-imidaza [1,2-α] pyridin-3-yl-
Sulfonyl) -N '-(4,6-dimethoxy-2-pyrimidinyl) -urea (TH-913, European Patent 0,23.
Example 1 of No. 8,070) B16) H1,3- (4,6-dimethoxypyridine-2-
Yl) -1- (2-ethoxyphenoxysulfonyl) urea,
(See German Patent Application P3816704.2, European Patent Application Publication No. 0,342,569). B17) Pyrazoxyfen, 2- [4-
(2,4-Dichloro-benzoyl) -1,3-dimethylpyrazol-5-yloxy] -acetophenone embedded image B18) benzofenap (MY71),
2- [4- (2,4-dichloro-m-toluoyl) -1,3
-Dimethylpyrazole-5-yloxy] -4'-methylacetophenone B19) dithiopyr, 5,5′-dimethyl 2-difluoromethyl-4-isobutyl-6-trifluoromethylpyridine-3,5-dicarbothioate embedded image B20) HW52, 2 ', 3'-dichloro-4-ethoxymethoxybenzanilide (see JP-A-60-42312) B21) Pyributicarb, O -3-
-Butylphenyl 6-methoxy-2-pyridyl (methyl) thiocarbamate embedded image B22) Anilofos, 4'-chloro-2-dimethoxyphosphinothioylthio-N-isopropylacetanilide embedded image B23) CH900, 1- (diethylcarbamoyl) -3-
(2,4,6-Trimethylphenylsulfonyl) -1,
2,4-triazole And B24) diamuron, 1- (1-methyl -1-
Phenylethyl) -3-p-toluyl-urea At least one compound B selected from the group consisting of
A herbicidal composition containing (B-type compound) in combination (provided that an effective amount of compound A is B1 to B4, B6 to B)
8, B17 to B20 and B22 except for the composition containing it in combination with only one compound B selected from the group consisting of). 2. In formula I, R ¹ is fluorine, chlorine, bromine, iodine, methoxy, nitro, cyano or --S.
(O) _n R ¹⁰ ; R ² and R ³ are independently of each other hydrogen, fluorine, chlorine, bromine, iodine, methyl, methoxy, trifluoromethoxy, cyano, nitro, trifluoromethyl, —SO ₂ R ¹¹ : NR ¹² R ¹³ , -N (CH ₃ )-
CO- R ¹⁴ or _{-CO -O- (C 1 -C 4)} - alkyl and is then ^{R 4, R 5, R 6} , R 7, R 8 and R ⁹ are each independently of the other hydrogen or methyl, The composition according to claim 1, which comprises a compound of formula I or a salt thereof. 3. In formula I, R ² and R ³ independently of one another are hydrogen, fluorine, chlorine, bromine, —N (CH ₃ ) ₂ ,
Methoxy, _{nitro, -SO 2 CH 3, -SO 2} CH 2 C
A compound according to claim 1 or 2 containing one or more compounds of formula I, or a salt thereof, which is 1, -SO ₂ N (CH ₃ ) ₂ or trifluoromethyl and n is 2. The composition as described. 4. From 1 to 99% by weight of a mixture of active substances of the compounds of the formula I of the type A and one or more active substances of the type B are contained in addition to the customary formulation auxiliaries. Item 4. The composition according to any one of items 1 to 3. 5. The method for producing the composition according to any one of claims 1 to 4, wherein a wettable powder, an emulsifiable concentrate, an aqueous solution, an emulsion, a spraying solution (tank mix), an oily or aqueous dispersion. Similar to conventional crop protection formulations selected from the group consisting of: foodstuffs, suspoemulsions, dusts, seed treatments, soil or dusting granules, water dispersible granules, ULV formulations, microcapsules or waxes. A process for the preparation of the above composition, characterized in that compound A is compounded with one or more compounds B. 6. A method for controlling an undesired plant, which comprises applying an effective amount of the composition according to claim 1 to an undesired plant or a place where the undesired plant is growing. . 7. The method according to claim 6, which selectively controls weeds in cultivated crops. 8. The method according to claim 7, wherein the cultivated crop is rice. 9. A method of using the herbicidal composition according to claim 1 for the selective control of weeds in cultivated crops.