JPH07215808A - Synergetically active composition for controlling undesirable plant in cropping - Google Patents

Abstract

PURPOSE: To provide a combined herbicide composition exhibiting excellent synergistic herbicidal action compared with the composition of prior arts and effective for inhibiting the growth of undesirable plants in rice culture. CONSTITUTION: This composition contains (A) a compound of the formula I [(i) (R<1> is ethoxy, propoxy or isopropoxy; R<2> is a halogen, NO2 , CF3 , CN, a 1-4C alkyl, a 1-4C alkoxy, a 1-4C alkylthio or a 1-4C alkoxy-carbonyl; (n) is 0-3) or (ii) (R<1> is a halogen, methoxy, ethyl or propyl; R<2> is a 1-4C alkoxy- carbonyl] at 6-position; (n) is 1); R<3> is H, a 1-8C alkyl or a 1-4C alkoxy; R<4> and R<5> are each H, a halogen, a 1-4C alkyl, a 1-4C alkoxy or a 1-4C alkylthio; Y is O or S; E is CH or N] or its salt and (B) a compound of the formula II (R<6> is H or a 1-6C alkyl) or its salt. The formulation ratio of A:B is 1:(1-40), preferably 1:(5-30).

Description

Detailed Description of the Invention

[0001]

This invention is in the field of plant protection agents that can be used against monocotyledonous and dicotyledonous weeds.

[0002]

PRIOR ART German patent application P3816704.2.
(European patent application WP-A-0 342 56
9), the same P3816703.4 (European patent application W
P-A-0342 568) and P3909053.
1 (European patent application WP-A-0 388 77
1) describes heterocyclic-substituted phenoxysulfonylurea compounds, which can be used to control a wide range of monocotyledonous and dicotyledonous weeds. They can be used both as soil herbicides and as transfoliar herbicides and also show a particularly high selectivity in monocotyledonous cultivated plants such as cereal plants, corn and rice.

[0003] German patent applications P3933543.7, P4031799.4 and P4209475.5 show various synergistic effects in controlling various weeds which are a major problem in cereals and rice. Mixtures of active compounds are disclosed.

[0004]

[Problems to be Solved by the Invention]
For example,Cyperus serotinus
(Cyperus),Sagittaria spp.
(Quie),Eleocharis spp. (Clog
Eye),Sirrpus spp. (Firefly) andE
chinochloa spp. (Hie) etc.
There are a large number of monocotyledonous weeds
Et al., Using only various mixtures as described above
Weeds cannot be weeded.

[0005]

Surprisingly, when applied in combination with the respective compounds mentioned above, they have a significant synergistic effect on their effectiveness against various weeds, and therefore P3934353.7 and P4209.
It has become possible to identify in her biological tests herbicidally active compounds which are superior to the respective combinations disclosed in 475.5.

The present invention includes A) the following formula (I)

[0007]

[Chemical 4]

[Wherein a ₁ ) R ¹ is ethoxy, propoxy or isopropoxy, and 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, and n represents 0, 1, 2 or 3, or a ₂ R ¹ is halogen, methoxy, ethyl or propyl at the ^2- position of the phenyl group, R ² is [(C ₁ -C ₄ ) alkoxy] carbonyl at the 6-position of the phenyl group, and n is 1. , And a
₁₎ and a ₂₎ is R ³ in each case hydrogen, saturated or unsaturated C ₁ alkyl or alkoxy of C ₁ -C ₄ in -C ₈ of, R ⁴ and R ⁵ are independently hydrogen mutually , Halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, in which the last three radicals are unsubstituted or halogen, C ₁ -C is substituted by ₄ alkylthio alkoxy or C ₁ -C _4, Y is O or S, and E is combined with a compound or a salt thereof represent CH or N], and that this B) The following formula (II)

[0009]

[Chemical 5]

[Wherein R ⁶ is hydrogen or C ₁
Is a C ₆ alkyl] or a salt thereof, or an active ingredient thereof and a herbicidal composition.

If desired, one or more known rice herbicides of very different structural groups can be used as additional combination ingredients. Of particular importance are compounds from the group of sulfonylurea compounds, urea compounds, amides, cyclohexanediones, thiocarbamates or chloroacetanilides.

The following various compounds may be mentioned as particular examples of such combination components, without restricting the invention to these: C1 AC-014 C2 anilofos C3 bentazone. ) C4 Bensulfuron-methyl (bensulfur)
on-methyl) C5 benzophenap C6 bromobutide C7 butachlor C8 butenachlor C9 cinmethylyl-CN cinnosulfuron (cynosulfuron) cin-sulfurulon (cin). 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 dimethamethrin
n) C16 dithiopyr C17 DPX-47 C18 esprocarb C19 4-ethoxybenz-2 ′, 3′-dihydrochloroanilide (HW-52) C20 phenoxaprop-ethyl (fenoxapr)
op-ethyl) or phenoxaprop-P-ethyl (fenoxaprop-P-ethyl) C21 imazosulfuron.
n) C22 JC940 [1- (2-chlorobenzyl)-
3- (α, α-dimethylbenzyl) urea] C23 MCPB C24 mefenacet C25 molinate C26 naproanilide C27 piperophos C28 pretilachlor
r) C29 propanil C30 pyrazosulfuron-ethyl (pyrazosu)
lfuron-ethyl) C31 pyrazoxyphen C32 pyrazolate C33 quinchlorac C34 simetrin C35 sulcotrione
[Chloromesulone,
ICI-A0051] C36 thiobencarb C37 2,4-D However, other rice herbicides may also be used to advantage with the combination compositions according to the invention.

Compound A is known from the German patent applications mentioned at the beginning of the text. Compounds of formula B are disclosed in European patent application EP 0 302 203. The stereochemistry in the formulas given for compounds A and B was not specified in detail. These formulas shall also include all geometric isomers, enantiomers and diastereomers and mixtures thereof, where stereoisomers may occur.

Compound DPX-47 = DPX-A894
7, i.e. N-[{(4,6-dimethoxypyrimidin-2-yl) aminocarboxyl} -1-methyl-4-
(2-Methyl-2H-tetrazol-5-yl) -1-
H-pyrazole-5-sulfonamide] has the following structural formula:

[0015]

[Chemical 6]

Compound AC-014, namely 1- [2-
(Cyclopropylcarboxylphenyl) sulfamoyl] -3- (4,6-dimethoxypyrimidin-2-yl) urea has the following structural formula:

[0017]

[Chemical 7]

And is disclosed in US Pat. No. 5,009,699 of June 22, 1990. Compound JC 940 is disclosed in Japanese Patent Application Publication J-6008725.
4 is disclosed.

Compound Imazosulfuron (TH-913)
Is disclosed in European patent application EP-A-0238 070 (see Example 1). Compound NSK-850, α-chloro-N- (3-methoxy-2-thienyl) -methyl-2 ′, 6′-dimethylacetanilide, was prepared by the procedure of M.I. Magazine "Weed R" by Ogasawara
research "(Tokyo), 1989, pp. 131-137.

The compound HW-52, 4-ethoxybenz-2,3-dihydrochloroanilide, is available from N.W. Ich
The magazine “Weed Research” by
h "(Tokyo), 1990, pp. 261-267.

The compound CH-900, 1-diethylcarbamoyl-3- (2,4,6-trimethylphenylsulfonyl) -1,2,4-triazole, is described in European patent EP-332133.

The compound sulcotrione (chloromethrone), 2- (2-chloro-4-mesylbenzoyl) cyclohexane-1,3-dione, is disclosed in European patent EP 0298680 (see page 13, compound No. 51A). . These other C-type compounds are described in "The Pestici" published by the British Crop Conservation Society (1991).
de Manual ", 9th edition.

Of particular importance, in formula (I) above, a ₁ ) R ¹ represents ethoxy, propoxy or isopropoxy, R ² is in the 6 position and has the abovementioned meaning, and n is Represents 0 or 1, and a ₁ ) and a
₂ ), R ³ represents hydrogen or C ₁ -C ₄ alkyl, R ⁴ and R ⁵ are halogen, C ₁ -C ₄
Of alkyl, C ₁ -C ₄ alkoxy or C ₁ -C ₄ alkylthio, wherein the last three radicals are unsubstituted or halogen, C ₁ -C ₄ alkoxy or C is substituted by the ₁ -C ₄ alkylthio, Y is O, and E comprises a compound or a salt thereof represent CH, an herbicidal compositions according to the invention.

Saturated or unsaturated alkyl and alkoxy are correspondingly straight-chain or branched alkyl or alkoxy groups and halogen is F, Cl, Br or I, preferably F or Cl.

The compounds of formula (I) are capable of forming salts such that the hydrogen of the --SO ₂ --NH group is replaced with a cation suitable for agricultural use. In general, these salts are metal salts, especially alkali metal salts, alkaline earth metal salts, optionally alkylated ammonium salts or organic amine salts.

Preferred herbicidal compositions as compound A include one or more compounds of formula A1, A2 and A3 below, which are as follows:

[0027]

[Chemical 8]

Specific examples of the compounds of the active substances mentioned in the claims include the following without limitation: A1 + B 2. A1 + B + C10 (NSK 850) 3. A1 + B + C11 (CH 900) 4. A1 + B + C25 (pretilachlor) Each combination composition according to the invention shows very good activity when applied together against a wide range of economically important monocot and dicot weeds. Even difficult-to-control perennial weeds that germinate from rhizomes, rhizomes or other conserved organs can be easily weeded by a combination of these active compounds. In this case, it is equivalent whether the substances are applied before sowing, before germination or after germination. The following are some representative examples of monocotyledonous and dicotyledonous weed flora that can be controlled by the combination composition according to the invention, without being limited to any particular species.

For monocotyledon weeds, for example, the species Echinochloa and Cyperus from the group of annuals, for perennial weeds are highly cold-resistant Cyperus.
Species are easily eradicated. Weeds that occur in rice under special cropping conditions, such as Sagittari
a , Alisma , Rotala , Monochori
a, Eleocharis, Scirpus, Cype
Rus and the like are markedly controlled by the combination of the active compounds according to the present invention.

When the herbicidal composition according to the invention is applied to the soil surface before germination, the germination of the seedlings of the weed is completely prevented, or the weed grows up to the germ layer stage but thereafter Their growth stops and they eventually die completely after 3 to 4 weeks.

When the combination of these active compounds is applied to the green plant parts or to the irrigation after germination of rice crops, a dramatic cessation of growth likewise occurs very rapidly after the treatment. Occur. Weeds either remain in the stage of development that was present at the time of application, or die more or less completely after a certain period of time, and thus the competition of weeds harmful to crop plants is a novel combination composition according to the invention. It can be eliminated in a permanent manner very early by the use of the product.

Although the composition according to the invention has excellent herbicidal activity against monocotyledonous and dicotyledonous weeds, the cultivated plant rice is only slightly or not inhibited. For this reason, the combination composition is very suitable for selectively controlling unwanted plant growth, especially in rice.

They are superior to the known herbicides and herbicidal combinations in their range of potency and potency and can be used in low dosages. Another advantage of these novel combination compositions is their continuous action, which lasts for several weeks, thus obviating the need for subsequent application of herbicides to newly germinated weeds. Therefore secondary work can be omitted because the growth of competitive weeds is excluded in only one application.

With the combination of active compounds according to the invention a herbicidal action is achieved which is greater than would be expected on the basis of the activity of the individual compounds. Such an increase in potency makes it possible to significantly reduce the amount of individual agonist compound used. The combination of these various herbicides can also result in an accelerated rate of action. Such properties bring significant benefits to users in the actual control of weeds. The user can control various weeds cheaper, faster, with less effort and increased persistence, which results in a large yield of one cultivated plant crop.

Furthermore, the fact that a safer or detoxifying action is remarkably present in a series of combinations of the action compounds, that is, the phytotoxic action of the action compound used is due to, for example, cultivation plants such as rice. It has been found that it can be reduced or completely eliminated.

The mixing ratio A: B can be varied within wide limits and is generally in the range 1: 1 to 1:40. The choice of mix ratio depends on the particular mix partner, the stage of weed development, the type of weed and the weather conditions.

Preferably A: B is 1: 5 to 1:30.
A compounding ratio such that The applied amount of herbicide A in the active substance mixture is preferably between 10 g / ha and 100 g / ha and the applied amount of herbicide B is 50 g / ha.
between g / ha and 600 g / ha. The applied doses for the various compounds from group C are very different because they are partly of different structural groups, and depending on the type of the active compound a few g to 3 kg per hectare. Is a range of active substances.

The combination of active compounds according to the invention may be applied in the customary manner with the two compounding ingredients present as a mixed preparation, which is diluted with water.
Alternatively, it may be prepared as a so-called tank mixture by diluting the individually formulated components together with water.

Compounds A and B, or combinations thereof with C can be formulated in different ways,
Based on that, various biological and / or physicochemical indicators are defined.

Possible suitable preparations are eg wettable powders (W
P), water-soluble powder (SP), water-soluble thickener, emulsion (E
C), aqueous solutions (SL), emulsions (EW), for example water-in-oil and oil-in-water emulsions, sprayable solutions or emulsions, oil-based or water-based dispersions, suspension thickeners (SC), (suspension emulsion), oil-soluble solution, capsule suspension (CS), powder dusting agent (DP), seed coating agent, granule for soil application or dusting application, microgranule, spray Various granules (GR), water-soluble granules (SG), water-dispersible granules (WG), ULV preparations, microcapsules or waxes in the form of granules, absorbent granules and adsorbent granules.

The respective types of these formulations are known in principle and are described, for example, by C.M. Hauser
Winnacker-published by Verlag (1986)
Kuechler's "Chemische Techn"
"Logie" Volume 7 (4th Edition), Marcel De
kker H. Y. Published by VanV (1972-73)
alkenburg's “Pesticide Form”
ations "(2nd edition), G. Goo, London
dwin Ltd. Published (1979) by K. Marte
ns's "Spray Drying Handboo"
k "(3rd edition).

The required formulation aids, such as various inerts, surfactants, solvents and other additives are likewise known, and are, for example, "Handbook of Architects" by Watkins, published by Darland Books, Coldwell, NJ.
Dust Dirients and Carrier
S ”(Second Edition), J. Wiley So, New York
H.n.s. v. Olphen's "Introduc
totion to Clay Colloid Chem
“Istry” (2nd Edition), Inters in New York
Science published (1950) by Marsden's "S
“Events Guide” (2nd edition), MC Publ. Co, Ridgewood, NJ
rp. Published by McCutcheon "Deterge"
nts and Emulsifiers Annua
Chem. Publ. Co., New York.
Inc. Published (1964) Sisley and Woo
d “Encyclopedia of Surfac
e Active Agents ", Stuttgart Wiss. Verlagsgesell.
976) Schoenfeldt's "Grenzfl
aechenextensive Athelenoxyd
addukte "and G. Hauser of Munich
Winnacker-published by Verlag (1986)
Kuechler's "ChemischeTechno"
logie ", Volume 7 (4th edition).

On the basis of these preparations also various combinations with other pesticidally active substances such as other herbicides, fungicides or insecticides and fertilizers and / or growth regulators, for example in the form of final preparations, Alternatively, it can be formulated as a tank mixture.

Wettable powders can be homogeneously dispersed in water and, in addition to their active compounds, in addition to diluents and inerts, various ionic and / or nonionic forms. Surfactants (wetting agents, dispersants) such as polyoxyethylenated alkylphenols, polyoxyethylenated fatty alcohols or fatty amines, fatty alcohol polyglycol ether sulfates, alkane sulfonates, alkylbenzene sulfonates, lignin sulfone The preparation also contains sodium acid salt, sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, sodium dibutylnaphthalene sulfonate or sodium oleoylmethyl taurine. In order to prepare wettable powders, the herbicidally active compounds are finely ground in a conventional apparatus such as a hammer mill, a blowing mill or an air jet mill, and at the same time or afterwards with a formulation aid. Mix.

The emulsions comprise one or more of their active compounds in organic solvents such as butanol, cyclohexanone, dimethylformamide, xylene or relatively high boiling aromatic compounds or hydrocarbons or mixtures of various organic solvents. It is prepared by dissolving with the addition of a surfactant (emulsifier) of the ionic and / or non-ionic type. Emulsifiers which can be used are, for example, calcium arylaryl sulfonates such as Ca-dodecylbenzene sulfonate or fatty acid polyglycol ethers, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, It is a nonionic emulsifier such as sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester or polyoxyethylene sorbitan ester.

Powder-dispersing compositions are obtained by grinding the active compounds with finely divided solid substances, for example talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.

The suspension thickener may be water-based or oil-based. They can be made using commercially available bead mills and, optionally, for example by wet milling with the addition of the various surfactants already mentioned above for the other formulation types.

Emulsions (EW), such as, for example, oil-in-water emulsions, can be mixed with various aqueous organic solvents and optionally with various surfactants such as those already mentioned above for the other formulation types. Equipment, colloid mill and /
Alternatively, it can be prepared by a static mixing device.

Granules may be prepared by spraying the active compound on an adsorbent granulated inert material or by spraying the active compound concentrate, for example with polyvinyl alcohol, sodium polyacrylate or coconut oil. Can be prepared by applying to the surface of a carrier material such as sand, kaolinite or a granulated inert material. Suitable active compounds can also be granulated in the manner customary for the production of fertilizers, if desired in admixture with various fertilizers.

Generally, water-dispersible granules are spray dried,
It is made by a variety of conventional methods such as fluid bed granulation, disk granulation, high speed mixer mixing and solid inert extrusion.

The agrochemical preparations generally contain 0.1 to 99% by weight, in particular 2 to 95% by weight, of the active compounds A and B and optionally C. The concentrations of active compounds A, B and C in the formulation can be different.

In the wettable powder, the concentration of the active compound is
For example, about 10 to 95% by weight, the balance which makes up 100% by weight consists of customary pharmaceutical ingredients. In the case of emulsions, the concentration of the active compound is about 1 to 85% by weight,
It may preferably be 5 to 80% by weight. The formulations in powder form contain from about 1 to 25% by weight, up to 5 to 20% by weight of the active compound, and the sprayable solution comprises from about 0.2 to 25% by weight, preferably 2 to 20% by weight. Contains active compounds. In the case of granules, for example water-dispersible granules, the content of the active compound depends, in part, on whether the active compound is present in liquid or solid form and how Depending on whether different granulation aids or fillers were used. Generally, in the case of water-dispersible granules, their content is between 10 and 90% by weight. In the case of spray granules which are sprayed directly into the douche, the active compound content is generally from 1 to 10
% Is preferred.

In addition, the active compound preparations mentioned above may optionally contain adhesives, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreeze agents and various solvents, fillers, carriers and colorants, Includes defoamers, evaporation inhibitors, and pH and viscosity enhancers that are conventional in those cases.

Each formulation which is present in the commercially available form for application is optionally in the customary manner, for example in the case of wettable powders, emulsifiable thickeners, dispersants and water-dispersible granules. Diluted with water. Preparations in the form of powders, granules for soil application or dusting and sprayable solutions are usually not further diluted with other inert substances before application.

The required dosages of compounds A and B will vary according to various external conditions such as temperature, humidity, above all the type of herbicide used. Rice crop herbicide additionally used (C)
The required amount of application of V will also vary depending on various external conditions as well.

[0056]

EXAMPLES The present invention will be described below with reference to some examples. A. Formulation example a) 10 parts by weight of the combination composition of active compounds according to the present invention and 90 parts by weight of talc as an inert substance are mixed and finely ground in a hammer mill to give a powder composition. can get. b) 25 parts by weight of the active compounds A + B, 64 parts by weight of kaolin-containing quartz as an inactive substance, 10 parts by weight of potassium ligninsulfonate as a wetting agent and a dispersant, and 1 part by weight of sodium oleoylmethyltaurine. By mixing and crushing with a spike crusher,
A wettable powder that is easily dispersible in water is obtained. c) 20 parts by weight of the active compound A + B, and an alkylphenol polyglycol ether [Triton X
207®), 3 parts by weight of isotridecanol polyglycol ether (8 mol EO), and paraffinic mineral oil (boiling range, eg about 255).
To 277 ° C. to 277 ° C.) and milled in a milling ball mill to a particle size of less than 5 microns to give a dispersion thickener which is readily dispersible in water. d) An emulsifiable thickener is obtained from 15 parts by weight of active compounds A + B, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of ethoxylated nonylphenol as emulsifier. e) The following components: Active compound A + B 75 parts by weight Calcium lignin sulfonate 10 parts by weight Sodium lauryl sulfate 5 parts by weight Polyvinyl alcohol 3 parts by weight Kaolin 7 parts by weight are mixed, crushed in a spike crusher, and the powder is flowed. Water-dispersible granules are obtained by spraying water as a granulating liquid in the bed to granulate. f) The following components Active compound A + B 25 parts by weight 2,2'-dinaphthylmethane-6,6'-5 parts by weight Sodium disulfonate sodium oleoylmethyl taurine sodium 2 parts by weight Polyvinyl alcohol 1 part by weight Calcium carbonate 17 parts by weight Water 50 parts by weight can be homogenized and pre-milled, then milled in a bead mill, and the resulting suspension can also be water-dispersed by atomizing in a spray tower with a single material nozzle and drying. Granules are obtained. B. Biological example 1. Pre-emergence action against weeds Seeds or rhizomes of various monocotyledonous and dicotyledonous weeds with diameter 9
Place in sandy loamy soil in a cm plastic pot and cover with soil. The various weeds that arise during the cultivation of rice are cultivated in soil saturated with water, with each pot being filled with water so that the water reaches the soil surface or a few millimeters above it.

Next, various combination compositions of active compounds according to the invention formulated in the form of wettable powders or emulsion thickeners, and in parallel tests the correspondingly formulated individual active compounds were coated with each of them. Applied to the soil or, in the case of rice, different amounts of water applied as an aqueous suspension or emulsion with an amount of water corresponding to 600 to 800 l / ha.

After the treatment, the pots are placed in a greenhouse and kept under good growth conditions for their weeds. A macroscopic evaluation of plant inhibition or inhibition of germination was carried out after germination of the test plants, after a test period of 3 to 4 weeks, in comparison with the untreated control group. Each herbicidal composition according to the invention has good pre-emergence herbicidal activity against a wide range of grass and various weeds.

In all cases, for each combination there was a difference between the calculated and the measured activity. The calculated degree of action that should be theoretically expected for a given combination is S. R. Colby: “Weeds” 15 ,
20-22 (1967), "Calculation of synergistic and antagonistic responses of herbicide combinations".

This formula is expressed as E = X + Y- [X.Y / 100] for a combination of two components, and E = X + Y + Z + [X.Y.Z / 1000 for a combination of three herbicidal compounds. ]-[(XY + XZ + YZ) / 100], where each symbol in these formulas respectively represents:% inhibition of herbicide A at an applied amount of X = xkg / ha Y = ykg / ha % Inhibition by herbicide B in amount Z =% inhibition by herbicide C at dose of z kg / ha E = x + y (or + z) by herbicide A + B (or + C) at dose of kg / ha % Of inhibition to be expected If the actual inhibition is greater than that to be expected in the arithmetic calculation, the effect of the combination is greater than the sum, ie synergism is present.

Each combination of active compounds according to the invention has a higher herbicidal activity than would be expected according to Colby, based on the effect observed when the respective compounds are applied alone. That is, the combination of those active compounds is synergistic. 2. Post-emergence action against weeds: Seeds or rhizomes of various monocotyledonous and dicotyledonous weeds are placed in sandy loam soil in plastic pots, covered with soil, and placed under good growth conditions. . The various weeds produced during rice cultivation are cultivated during the experimental period in each pot where the water reaches 3 cm above the soil surface. Approximately 2-3 weeks after sowing, each test plant is treated at its 2-3 leaf stage.

Various combinations of active compounds according to the invention, formulated as wettable powders or emulsion thickeners, and in parallel tests, different active doses of each of the correspondingly formulated individual active compounds, 600 to 8
The action of each preparation after spraying on the green plant parts with an applied amount of water equal to 001 / ha and leaving the test plants in the greenhouse under optimal growth conditions for about 3 to 4 weeks. Are visually evaluated in comparison with the untreated control group. In the case of weeds grown in rice cultivation, these active compounds are either added directly into the irrigation (application method similar to the application of so-called granules), or onto those plants and the irrigation. Spray inside. Even after germination, the compositions according to the invention have good herbicidal activity against a wide range of economically important grass and various weeds. The action of the composition according to the invention is synergistic according to Colby's analysis. 3. Cultivation capacity of cultivated plants In several other tests in greenhouses, relatively large numbers of cultivated plants and weed seeds are placed in sandy loam soil and covered with soil. Rice is grown as paddy rice in soil saturated with water.

Some of the pots were treated immediately as described in 1 above, others were placed in the greenhouse until the plant had formed 2 or 3 leaves, and then the book as described in 2 above. The composition of the active compound according to the invention is sprayed and, for comparison, only a single active compound is sprayed at different application rates. In paddy rice, application is also carried out in some cases by throwing the active compounds or their formulations into irrigation.

Each composition of the active compounds according to the invention by macroscopic evaluation after two weeks in the greenhouse after application does not inhibit various crops before and after germination even at high active compound doses. Is confirmed. They protect Gramineae crops such as wheat and rice. Therefore, each combination of active compounds according to the invention shows a high selectivity when applied to control undesired plants that grow in agriculture.

The results of each selected test are shown below in tabular form. Note: 1): 1-[(2-ethoxyphenoxy) sulfonyl] -3- (4,6-dimethoxypyrimidinyl) urea (as a 20% strength wettable powder) 2): DEH as a 10% strength emulsion 112 3): Anilophos as a 10% strength wettable powder 4): 100% complete inhibition, 0% without inhibition Note: 1) to 3) are the same as in Table 1. 4): Average% of seed weight of untreated rice 5): Standard deviation of average 6): 10 = complete inhibition
7): G = growth inhibition

 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Klaus Bauer Germany, 63456, Hanau, Dorner Strasse, 53 days (72) Inventor Hermann Bielinger, Germany, 65817 Eppschyustein, Eichen Wake, 26

Claims (10)

[Claims] 1. A) The following formula (I): [Wherein a ₁ ) R ¹ is ethoxy, propoxy or isopropoxy, and 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, and n represents 0, 1, 2 or 3, or a ₂ ) R ¹ is halogen, methoxy, ethyl or propyl at the ^2- position of the phenyl group, R ² is [(C ₁ -C ₄ ) alkoxy] carbonyl at the 6-position of the phenyl group, and n is 1. , And in each case a ₁ ) and a ₂ ) R ³ represents hydrogen, saturated or unsaturated C ₁ -C ₈ alkyl or C ₁ -C ₄ alkoxy, and R ⁴ and R ⁵ are the same as one another. Independently hydrogen,
Represents halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, with the last three radicals being unsubstituted or halogen, C ₁ -C is substituted by ₄ alkylthio alkoxy or C ₁ -C _4, Y is O or S, and E is combined with a compound or a salt thereof represent CH or N], and that this B) The following formula (II): [Wherein R ⁶ is hydrogen or C ₁ -C ₆ alkyl] or a salt thereof, and an active ingredient.
Herbicidal composition. 2. In the formula (I), a ₁ ) R ¹ represents ethoxy, propoxy or isopropoxy, R ² is in the 6 position and has the abovementioned meaning, and n represents 0 or 1. And a ₁ ) and a
₂ ), R ³ represents hydrogen or C ₁ -C ₄ alkyl, R ⁴ and R ⁵ are halogen, C ₁ -C ₄
Of alkyl, C ₁ -C ₄ alkoxy or C ₁ -C ₄ alkylthio, wherein the last three radicals are unsubstituted or halogen, C ₁ -C ₄ alkoxy or C ₁ -C is substituted by ₄ alkylthio, Y is O, and E comprises a compound or a salt thereof represent CH, composition of claim 1. 3. The following formulas A1, A2 and A3: The composition according to claim 1 or 2, which comprises each of the compounds or a salt thereof. 4. A composition according to claim 1, which contains, in addition to the customary compounding auxiliaries, 0.1 to 99% by weight of active compounds A and B. 5. The composition according to claim 1, which comprises the active compounds A and B in a weight ratio of 1: 1 to 1:40. 6. A wettable powder, an emulsion, an aqueous solution, an emulsion,
Granules in the form of sprayable solutions, oil-based or water-based dispersions, suspension emulsions, suspension thickeners, oil-soluble solutions, capsule suspensions, microgranules, spray granules, absorbent granules and adsorbent granules. An ordinary plant protection agent formulation of the group consisting of an agent, a powder application composition, a seed coating composition, a soil or application granule, a water dispersible granule, a ULV compound, a microcapsule and a wax agent. The method for producing the composition according to claim 1, wherein compound A and compound B are similarly mixed. 7. A method of controlling unwanted plants, which method comprises applying to the plants or to their cultivated land a herbicidally effective amount of the composition of any of claims 1-5. 8. The method according to claim 7, wherein weeds are selectively exterminated in the planting of useful plants. 9. The method of claim 8, wherein the crop of useful plants is rice. 10. A method of using the herbicidal composition according to claim 1 for the selective control of weeds in rice cultivation.