JPS5838264A - Novel urea derivative, manufacture, composition containing same and herbicidal use - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention provides a novel N-phenylsulfonyl-N'-pyrimidinyl- and -triazinyl-urea having herbicidal activity and plant growth regulating properties, a method for producing the same, and a novel N-phenylsulfonyl-N'-pyrimidinyl- and -triazinyl-urea containing the urea derivative as an active ingredient. and its use for controlling weeds, in particular for selectively controlling weeds in crops of useful plants or for suppressing plant growth.

The N-phenylsulfonyl-N'-pyrimidinyl- and nitriazinyl'-ureas according to the invention have the general formula I: (wherein A is a halogen atom, an alkoxy group having 1 to 4 carbon atoms, and 1 carbon atom). 4 alkylthio group, C1 to C4 alkylsulfinyl group, C1 to C4 alkylsulfonyl group,
by a C1 -C4 halogenoalkoxy group, a C1 -C4 halogenoalkylthio group, a C1 -C4 halogenoalkylsulfinyl group or a C1 -C4 l-s Qgenoalkylsulfonyl group It represents a substituted alkyl group having 1 to 6 carbon atoms, or 9 represents an alkenyl group having 2 to 6 carbon atoms substituted with each of the above groups.

E represents a meden group or a nitrogen atom, X is an oxygen atom,
represents a sulfur atom, sulfinyl or a sulfinyl group, Z represents an oxygen atom or a sulfur atom Y, m is 1 or 9 is 2
represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or a -Y-R5 group, and chicken represents a hydrogen atom, a halogen atom, a carbon atom, and Alkyl group having 1 to 5 atoms, 1 alkenyl group having 2 to 5 carbon atoms, halogenoalkyl group having 1 to 4 carbon atoms or -Y-R,, -COOR,, -N
o, or -CO-NR, -- group, and the island is a hydrogen atom, a C1-C4 alkyl group, or a C1-C4 alkoxy group.

C 1 -C 4 alkylthio group, C 1
1 to 4 halogenoalkyl group, a halogen atom or a halogenoalkoxy group having 1 to 4 carbon atoms, or an alkoxyalkyl group having more than 4 carbon atoms; represents an alkoxy group or a C1 to C40 Ilogenoalkyltheo group, and the above - and the above - respectively represent an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkenyl group having 2 to 5 carbon atoms; 6 represents an alkynyl group, and the above and the above - independently represent a hydrogen atom, a C1 to C5 alkyl group, a C2 to C5 alkenyl group, or a C2 to C6 alkynyl group. and the above Y represents an oxygen atom, a sulfur atom, or a sulfinyl or sulfonyl bridge, and provided that the above X represents an oxygen atom, the above A may also represent an unsubstituted alkenyl group t having 2 to 6 carbon atoms. ) and salts of these compounds.

Urea compounds, triazine compounds and pyrimidine compounds having herbicidal action are generally known. Regarding arylsulfamoyl-heterocyclyl-aminocarbamoyl compounds having herbicidal and plant growth regulating effects,
In recent years, for example, Dutch Patent No. 121,788, European Patent Publications No. 2419 and No. 23,422, US Pat. No. 1,468,7
It is disclosed in the specification of No. 47.

In the above definition, an alkyl group is a straight-chain or branched alkyl group, such as a methyl group, an ether group, an n-propyl group, an i-propyl group, an amyl group in the four isomeric forms, an n-amyl group, an i-amyl group. group, 2-amyl group, 3-amyl group, n
-hexyl and i~hexyl are to be understood as meaning.

Alkoxy group means methoxy group, ethoxy group, n-propoxy group, i-propoxy group and four isomeric butoxy groups, but especially methoxy group, ethoxy group or i-globoxy group. I would like to be understood as

Examples of alkylthio groups are methylthio, ethylthio, n
-propylthio, i-propylthio and n-butylthio, but especially ethylthio and ethelthio.

Examples of alkenyl groups are vinyl group, allyl group, isopropenyl group, prop-1-enyl group, fth-1-enyl group, fth-2-enyl group, f-3-enyl group, and isobuty-enyl group.
1-enyl group, isobut-2-enyl group, pent-1-
enyl group, pent-2-enyl group, pent-5-enyl group and pent-4-enyl group, but especially bi=ni group, 11)yl group and oyohyhent-4-enyl group.

Examples of alkylsulfinyl groups are methylsulfinyl group,
ethylsulfinyl group, n-7''o hA/sulfinylfioj, n-butylsulfinyl group, but especially methylsulfinyl group and ethylsulfinyl group theal.

Examples of alkylsulfonyl groups are methylsulfonyl group,
Ethylsulfonyl, n-clobylsulfonyl and n-butylsulfonyl groups, but especially methylsulfonyl and ethylsulfonyl groups.

In the above definitions and in the halogeno-alkyl group, -alkoxy group, -alkylsulfinyl group, -alkylsulfonyl group and alkylthio group, the halogen atom means a fluorine atom, a chlorine atom or a bromine atom, preferably a fluorine atom. or chlorine atom [to be understood].

Preferred halogenoalkyl groups (which are also constituents of larger substituents, e.g. halogenoalkoxy or halogenoalkyl groups) are difluoromethyl, trifluoromethyl, hefluoroethyl groups.
2,2.2-) Lifluoroethyl group, chlorofluoromethyl group, bromofluoromethyl group, 2-chloroethyl group, 1,1.2.2-tetrafluoroethyl group, 2-fluoroethyl group, 2,2, 2-trichloronibble group, bromodifluoromethyl group, chlorodifluoromethyl group,
1,1.2-)') fluoro-2-chloroethyl group,
Ll, 2-toIJ fluoro-2-bromoether group and 1.1.2.3.3.3-hexafluoroglobyl group, but especially difluoromethyl group, 2.2.2-
)! J fluoroethyl group and perfluoroethyl group.

In the definitions of the symbols above, the alkynyl group is generally 7'o
Pargyl group, but-2-ynyl group, but-3-ynyl group and isomeric benzonyl and hexynyl groups, preferably propargyl group or but-2- or -6-ynyl group.

The invention also relates to salts formed by the compounds of formula I with amines, alkali metal and alkaline earth metal bases and quaternary ammonium bases.

Among the alkali metal and alkaline earth metal hydroxides, lithium, sodium, potassium, magnesium and calcium hydroxides, especially sodium and potassium hydroxides, are preferred salt formers.

Examples of amines suitable for salt formation are aliphatic and aromatic primary, secondary and tertiary amines, such as methylamine, ethylamine, propylamine, i-propylamine, the four isomeric butylamines. , dimethylamine, diethylamine, jetanolamine, dipropylamine, diisopropylamine, di-n-butylamine, pyrrolidine, piperidine, morpholine, trimethylamine, triethylamine, tripropylamine, quinuclidine, pyridine, quinoline and i-quinoline. , especially ethylamine, globilamine, diethylamine and triethylamine, and especially impropylamine and jetanolamine.

Examples of quaternary ammonium bases are typically cations of ammonium halide salts, such as tetramethylammonium cation, trimethylbenzylammonium cation, triethylbenzylammonium cation, tetramethylammonium cation, trimethylethylammonium cation and ammonium cation.

Preferred compounds of formula I according to the invention are a)
X or b) Z represents an oxygen atom, C) m represents a number of 1, and d) the sum of the number of carbon atoms in the group - and the group is not more than 4.

A preferred combination of limiting conditions is 1 in formula I, where X and Z are oxygen atoms y! ', m represents the number 1 and the group -X-A is in the 2-position relative to the sulfonyl group,
A further preferred group of compounds is given below.

Within this group, preferred compounds are further those in which the sum of the number of carbon atoms in groups 1 and 9 is greater than 4.

Particularly preferred compounds in this subgroup are those represented by a halogenoethoxy group or a halogenomethoxy group Y. Of these, nine are 2.2. ．． Those represented by a 2-1-lifluoroethoxy group or a difluoromethoxy group 7 are sequentially preferred.

1'l? A preferred compound is N-(2-difluoromethoxyphenyl-sulfonyl)-N'-(4-me)oxy-6-(2,2,2-trifluoroethoxy)=1.
3.5-)riazin-2-yl]-urea, N-(2-(
2-chloroethoxy)-phenylsulfonyl) -N
'-(a-methoxy-6-(2,2,2-)lifluoroethoxy)-1,3,5-triazin-2-y/'
) -[,N-(2-trifluoromethoxyphenylsulfonyl)-N'-(4-difluoromethoxy-6-
Methyl-pyrimidin-2-yl)-urea and N-(2
-difluoromethoxyphenyl-sulfonyl) -N
'-(4-difluoromethoxy-6-medellupyrimidin-2-yl)-urea.

formula! The compound represented by is prepared in an inert organic solvent.

According to the first method, the above formula! The compound represented by
The phenylsul7onamide represented by the following formula (in the formula, A, R,, R,,
E, R1, R4 and Z have the meanings defined in formula I above, and all represents a hydrogen atom, a halogen atom, a nitro group or an alkyl group having 1 to 3 carbon atoms. ) in the presence of a base.

According to the second method, the compound represented by the formula ■ is obtained by the following formula ■
: (In the formula, A, R4, R1, m, X and Z represent the meanings defined in the above formula I.) Phenylsulfonyl isocyanate or inthiocyanate represented by the following formula ■: (In the formula, E, R3
And the mountain is the above formula! represents the meaning defined in ) in the presence or absence of a base.

According to another method, the compound represented by the above formula (1) is a sulfonamide (where E, R,
, R, and Z have the meaning defined in formula I above. ) with an isocyanate or inthiocyanate in the presence or absence of a base.

Finally, the compound represented by the above formula I has the following formula (■): (wherein A, R4, island, m and X represent the meanings defined in the above formula!, and L-(all is a hydrogen atom, or a halogen atom, a nitro group or an alkyl group having 1 to 3 carbon atoms. I can do it.

If desired, the resulting urea derivative of formula I can be converted into an addition salt with an amine, an alkali metal or alkaline earth metal hydroxide or a quaternary ammonium base. This conversion is effected, for example, by reaction with equimolar amounts of base and evaporation of the solvent.

Typical starting materials for the starting materials represented by formulas I, N, and ■ above as well as specific sulfonamides represented by formula ortho-substituted hydroxyphenyl- or substituted ortho-hydroxyphenyl-sulfonamides having the meaning as defined in formula I and X' represents an oxygen atom or a sulfur atom) are described in European Patent Publication No. 44,807. Disclosed in the issue.

Some of the starting materials represented by formulas (1), (2) and (2) above are known. The novel compounds represented by the above formulas (1) and (2) can be obtained from the corresponding compounds represented by the above formula (2) by conventional means.

The novel fluoroalkoxyaminopyrimicunes and monotriazines of formula (1) above, their preparation, and the corresponding compounds of formulas I and (2) are disclosed in Swiss Patent Application No. 3527/82-8. has been done.

The reaction to obtain the compound of formula (1) above is preferably carried out in a neutral, inert, organic solvent such as methylene chloride, tetrahydrofuran, acetonitrile, dioxa/and Toluev. Bases that can be used are organic bases, amines such as triethylamine, quinuclidine, quinoline, pyridine, etc., and inorganic bases, such as hydrides such as sodium hydride or calcium hydride, hydroxides such as hydroxide).
carbonates such as sodium carbonate and potassium carbonate, and bicarbonates such as potassium bicarbonate and sodium bicarbonate.

The reaction temperature is preferably in the range -20° to +120°C. The reaction usually proceeds slightly exothermically and may be carried out at room temperature. In order to shorten the reaction time or to start the reaction, the mixture is suitably metered briefly at the boiling point.

The final products can be isolated by concentrating the mixture and/or removing the solvent, and the resulting solid residue can be removed from solvents in which they are not readily soluble, such as ethers, aromatic hydrocarbons. and can be purified by recrystallization or grinding in chlorinated hydrocarbons.

The active ingredient represented by formula (■) is a stable compound. No special considerations are required when handling these.

When using a relatively small amount, use the above formula! The compound represented by has good selective growth inhibition and selective herbicidal properties,
This makes the above compounds highly useful for growing useful plants, especially grains, cotton, dice, corn and rice. It will be shown. In some cases, traditionally
Weed beds that can only be affected by all herbicides can also be damaged.

The mode of action of these active ingredients is unique. Many of them are movable. That is, they are accepted by the plant and translocated to other parts, where they act. Therefore, for example, by applying a surface treatment to perennial weeds, it is possible to damage even the roots. Compared to other herbicides and growth regulators, the novel compounds of formula I above are effective even when applied in very small amounts.

The compound represented by the above formula (2) also has strong plant growth regulating properties, which results in increased cropping rates or yields. Furthermore, the compound represented by the above formula (2) exhibits a concentration-dependent effect on inhibiting plant growth. Growth of both monocotyledonous and dicotyledonous plants is inhibited.

Therefore, for example, in agriculture in the tropics, intercropping (co
A legume that is often planted as ver crops)! ' can be selectively inhibited by the compound represented by formula I above, and as a result, although soil erosion between crops is prevented, competition between intercrops and crops can be suppressed.

Suppression of plant growth also allows many crops to be planted closer together, which can result in increased yields in terms of soil area.

The mechanism of yield increase by growth inhibitors is based on the fact that while limiting plant growth, more nutrients help in flower and fruit formation.

Compounds of formula I above can also be used to prevent sprouting from stored potatoes. When potatoes are stored throughout the winter, sprouts often develop. Shrinkage, weight loss and decay will also be reduced.

When applied in relatively large amounts, the growth of any test plants can be inhibited to the extent that the plants die.

The present invention also provides herbicidal and plant growth regulating compositions containing the novel active ingredient represented by the above formula 1, as well as methods for pre- and post-emergent control of weeds, monocotyledonous plants and dicotyledonous plants, especially weeds. grasses, tropical intercrops and tobacco plant side-shoots
), and a method for regulating the growth of plants, particularly leguminous plants.

The compounds of formula (II) above may be used in unmodified form or preferably as a composition together with auxiliaries customarily used in compounding technology and can therefore be prepared in known manner, e.g. It is processed into emulsified carbon concentrates, solutions that can be sprayed directly or diluted, dilute emulsions, wettable powders, soluble powders, dusts, granules or compositions encapsulated, for example, in polymeric substances.

Depending on the dosage form of the composition, the method of application, for example spray, mist, dusting, dusting or watering, is selected depending on the purpose and the given environment.

Formulations, i.e. compositions, comprising an active ingredient of formula I and optionally solid or liquid additives,
The formulation or compound can be prepared by known methods, e.g.
It is prepared by homogeneous mixing and/or milling with fillers such as solvents, solid carriers and optionally surface-active compounds (surfactants).

Suitable solvents are aromatic hydrocarbons, preferably 8 to 12
of carbon atoms, for example xylene mixtures or substituted naphthalenes, phthalate esters such as dibutyl phthalate or dioctyl phthalate, aliphatic hydrocarbons such as cyclohexane or paraffin, ethanol, ethylene glycol, ethylene glycol monomedel Alcohols, glycols and their ethers and esters, such as ethers or monoethyl ether;
a strong polar solvent such as a ketone such as cyclohexanone, N-methyl-2-pyrrolidone, dimethylsulfoxide or dimethylformamide; and an epoxidized vegetable oil such as epoxidized coconut oil or soybean oil; or water.

The solid carriers used, for example for dusts and dispersible powders, are the usual mineral fillers such as calcite, melk, kaolin, montmorillonite or attapalgite. A highly dispersed silicic acid or a highly dispersed polymeric adsorbent can also be added to the adsorbent. Suitable granular adsorbent carriers are porous, for example pumice, crushed brick, sepiolite or bentonite; Non-absorbent carriers & materials such as calcite or sand.Furthermore, a large number of inorganic or organic pre-granulated materials can be used, such as in particular dolomite or plant residue powders.

Depending on the nature of the compound of formula I to be formulated, suitable surface-active compounds include nonionic, cationic and/or anionic surfactants with good emulsifying, dispersing and wetting properties. Become. "Surfactant" candy is right,
It is understood that mixtures of surfactants are also included.

Suitable anionic surfactants can include both water soluble soaps and water soluble synthetic surfactant compounds.

Suitable soaps are alkali metal salts, alkaline earth metal salts or unsubstituted or substituted ammonium salts of higher fatty acids (CzeCo), for example oleic acid or stearic acid or natural fatty acid mixtures obtained for example from coconut oil or tallow oil. It is the sodium or potassium salt of

Fatty acid methyltaurate salts may also be mentioned.

However, so-called synthetic surfactants, in particular aliphatic sulfonates, aliphatic sulfates, sulfonates of benzimidazole derivatives or alkylaryl sulfonates, are more frequently used.

Aliphatic sulfonates or sulfates are usually alkali salts,
in the form of alkaline earth metal salts or unsubstituted or substituted ammonium salts, containing C8-C22 alkyl radicals, including also the alkyl part of acyl radicals, i.e. lignin sulfo/acids, dodecyl sulfuric acid; esters or sodium or calcium salts of fatty alcohol sulfates obtained from natural fatty acids. These compounds also include sulfuric esters of aliphatic alcohol-V ethylene oxide adducts and salts of sulfonic acids. The sulfonated benzimidazole derivative preferably contains two sulfonic acid groups and one fatty acid group having 8 to 22 carbon atoms. Examples of alkylarylsulfonates are the sodium, calcium or triethanolamine salts of dodecylbenzenesulfonic acid, dibutylnaphthalenesulfonic acid or naphthalenesulfonic acid/formaldehyde condensates. Corresponding phosphates, such as the abovementioned salts of phosphoric esters of p-nonylphenol and 4 to 14 mol of ethylene oxide, are also suitable.

or polyglycol ether derivatives of cycloaliphatic alcohols and/or of saturated or unsaturated fatty acids and alkylphenols, in which the derivatives contain 3 to 30 glycol ether groups and 8 to 20 carbon atoms in the (aliphatic) hydrocarbon moiety. and the alkyl moiety of alkylphenol K 6
It has 18 carbon atoms.

Further suitable non-ionic surfactants are polyethylene oxide, polypropylene glycol, ethylenediamine polyglobylene glyco-y and 1 to 10% of the alkyl chain.
It is a water-soluble adduct with an alkylboriglopylene glycol having from 10 to 250 ethylene glycol ether groups and from 10 to ioo globylene glycol ether groups. These compounds usually contain 1 to 5 glycol units per propylene glycol unit.

Typical examples of nonionic surfactants are nonylphenol, polyethoxyethanol, castor oil polyglycol ether, polyglobylene/polyethylene oxide, tributylphenoxyethoxyethanol, polyethylene glycol and octerphenoxybolyethoxyethanol. Fatty acid esters of polyoxyethylene sorbitan, such as polyoxyethylene sorbitan trioleate, are also suitable nonionic surfactants.

Cationic surfactants contain as N-substituents a small number (at least one polyglycol ether group or carbon atoms of 8 to 22
A quaternary ammonium salt containing an alkyl group and further a lower unsubstituted or halogenated alkyl, benzyl or lower hydroxyalkyl group as an N-substituent is preferred.

These salts are in the form of halides, methyl sulfate or ether sulfate, such as stearyltrimethylammonium chloride or benzyl chloride (2-
Chloroethyl)ethyl ammonium bromide is preferred.

Surfactants commonly used in formulation technology are described, for example, in the publications listed below.

Annual Report on Detergents and Emulsifiers by Mac Katcheotsu (M
c Cutcheon's Detergents a
nd Emulsifiers Annual), Mauk Publishing, Ringwood II-Chassis, 1979;
clopedia of 5urfaceActive
Agents)', Kagaku Publishing, New York, 96
4 Herbicides generally contain 1 to 95 - preferably 111 to 80 t of a compound of the formula (1), 1 to 999 t of a solid or liquid auxiliary, and 1 to 25% of a surfactant YO, preferably 0.1 to 25%. Contains

Particularly preferred formulations are those consisting of the following ingredients (ch = weight percentage): Emulsion concentrate active ingredient = 1 to 20q6 preferably 5 to 10% Surfactant = 5 to 30% preferably 10 or 20
Liquid carrier: 50 to 94% preferred, (70 to 8%)
Powder active ingredient - 01 to 10% preferably 11.1 to 1% Solid carrier: 999 to 90% Preferably 999 to 99% Susbenzilan concentrate active ingredient: 5 to 75% preferably 10 to 50% Water: 94% 25% to 25%, preferably 90 to 30% Surfactant: 1 to 40%, preferably 2 to 60% Wettable powder active ingredients: 05 to 90%, preferably 1 to 80% Surfactant: Q, 5 to 20 % Preferably 1 to 15% Solid carrier: 5 to 95% Preferably 15 to 90% Granule active ingredient: A5 to 50% Preferably 15% Solid carrier: 995 to 70% Preferably 97 to 8
Concentrated compositions are preferred as commercially available products, while end consumers generally use diluted compositions. Depending on the usage situation, the active ingredient (can be diluted up to 1,001%).
Generally, 9 active ingredients per hectare [1,01 to 10 Kf, preferably [1,025 to 5 Kf].

The compositions may also contain other additives, such as stabilizers, defoamers, viscosity regulators, binders, thickeners and fertilizers or other active substances for achieving specific effects.

In the examples below, the temperature is in degrees Celsius and the pressure is in Millipards mb.

Preparation Example a) 2-difluoromethoxyphenyl-sulfonyl isocyanate 124.6f in dioxane 1001, 2-amino-4-chloro-6-medoxy 1.3,5-triazine 80.3y in anhydrous dioxane 400d , added dropwise over 10 minutes. The reaction mixture was warmed to 90-100°C for 3 hours, then the solution was cooled and concentrated, mp 167-IS8°CP)N-(
2-difluoromethoxyphenyl-sulfonyl)-N
'-(4-chloro-6-medoxy1.3.5-triazin-2-yl)-urea 1801 available.

b) N-(2-difluoromethoxyphenyl-sulfonyl)-N'-(4-chloro-6-medoxy 1.3.
5-)Ryazin-2-yl)-urea 82, dioxane 60ml 1.2, 2.2-1 realoloethanol 20d
and potassium carbonate 5.5F at 55-60°
Stir for 12 hours at , then dissolve in 300 ml of water and filter over activated carbon. The mixture is acidified with 2N hydrochloric acid and the precipitated product is separated by filtration. Yield: N-(2-difluorome)-11- with melting point 155-157°
diphenyl-sulfonyl) -N'-[4-methoxy7
-6-, (2,2,2-trifluoroethoxy) -1
,3,5-)riazin-2-yl]-urea7.7 P
0 'IIIJ 2 m N-(2-difluoromethoxyphenylsulfonyl) -N'-(4-difluoromethoxy-6-methyl-pyrimidin-2-yl)-urea a) Gaseous difluorochloromethane Kaorui 500@(
The mixture is passed for 12 hours at a temperature of 70 DEG to 75 DEG C. into a solution consisting of 62.5 y of 2-amino-4-hydroxy-6-funal-pyrimidine in 1', 100 ml of a 40 ml solution and 100 ml of dioxane. During this period, the same amount of solid sodium hydroxide is added every hour, giving a total of 160y. The organic phase is separated and concentrated to about 1/10 of its volume, the residue is poured into water and the precipitated solid is separated, melting point 136-
2-Amino-4-difluoromethoxy-6- at 157°C
39.9jlEY of methyl-pyrimidine is obtained.

b) 2-difluoromethoxyphenyl-sulfonyl
Isocyanate 2.591.2-Amino-4-difluoromethoxy-6-methyl-pyrimidine t75jF and anhydrous dioxane"rOml 1g are stirred for 2 hours at a temperature of 70-75°C. The solution is evaporated and the residue is crystallized from ether. N-(2-
difluoromethoxydiphenyl-sulfonyl)-N'
-(4-difluoromethoxy-6-methyl-pyrimidin-2-yl)-urea4. o y Y get.

Loftoxy-6-meterubirimidin-2-yl)-urea a) Phenylchloroformate 3.9y (0,025 mol) and 4-dimethylamino-pyridine 0.05P'
2-Amino-4- in Y anhydrous tetrahydrofuran 30d
Difluoromethoxy-6-methyl-pyrimidine 9.09
(0.05 mol) is added continuously to the solution. The solution is stirred for 24 hours at -25 DEG C., then the reaction mixture is diluted with 250 d of ethyl acetate and the precipitate is separated.

Thus, 2-amino-4-difluoromethoxy-6-methyl-pyrimidine with a melting point of 204-205°C (decomposed)
Hydrochloride 5.1non is obtained. To remove remaining starting material, FM was transferred to an ion exchanger (MERK).
CK)) and the eluate is dried over sodium sulfate and evaporated.

4. 2-phenoxycarbonylamino-4-difluoromethoxy-6-methyl-pyrimidine as crude product in the form of a viscous oil. Get OF.

After crystallization, the product has a melting point of 56-58°C.

1H-NMR (CDC15): δ = 2.5 (S, CHs) + a4s (s, IH
), 7.0-7.5 (5H), 7.56 (t, J
==70 Hz, CHFz) and 9.0(NH)
ppm b) 1,5-diazabicyclo(5,4,0)undegun-5-ene 18F (α012 mol), 2-phenoxycarbonylamino-4-difluoromethoxy-6-methyl-pyrimidine 15y in the form of crude product (0,012
mol) and 2-(2
-ethoxy-ethoxy)-benzenesulfonamide)”
2.9 j/(0,012 mol) and the mixture is stirred for 1 hour at 420 DEG-25 DEG C., then diluted with 5,001 ml of water and acidified with hydrochloric acid. The separated oil is extracted into 200xl ethyl acetate and the mixture is dried over sodium disulfate and evaporated. The oily residue crystallizes from ethyl ether and acetone to give a yield of z7 as colorless crystals, melting point 90-95°C (decomposition).
N-(2-(2-ethoxy-ethoxy)-phenyl-
sulfonyl)-N'-(4-difluoromethoxy-6
-Metelupi 1 rimidine-2-I)-Urea is obtained.

2-Amino-14-mercapto- in gaseous difluorochloromethane 1αOy poppymethylformamide 100d
70-7 to 6-methoxy-1,3,5-) riazine and 48 grams of potassium carbonate.
Pass for 90 minutes at a temperature of 5°C. The reaction mixture is evaporated and the residue is stirred with water to separate the solid precipitate, which has a melting point of 146
2-amino-4-difluoromethylthio- at -150°C
6-medoxy 1.5.5-) riazine t6p available.

40qb water-oxidized) 2- in 100d of IJum solution
16.4 grams of amino-4,6-dichloropyrimidine*7'j (stir for 1 hour at a temperature of 95-100°C. 200 g/ya/y of dioxane are added and 20 py of gaseous difluorochloromethane 70-75° C. The organic phase is separated off and concentrated to about 115 ml of its volume, the residue is poured into water and the solid precipitate is separated, melting at 118-119°C.
2-amino-4-chloro-6-cyfluoromethoxypyrimidine 6P is obtained.

Example 6: 2-amino-4-? Fluoromethoquine-6-
Methoxy-pyrimidine 2-amicou 4,6-cymethoxypyrimidine hydrochloride 19.2jEY When heated at 150°C for 2 hours, during which time methyl chloride was removed, 2-amino-4-hydroxy-6-medoxypyrimidine Get a link. 40% sodium hydroxide solution 80 resistant and dioxane 100ml 1'
7 and then 1-difluorochloromethane 22 f'
Pass at 70-75' for 3y4 hours. The organic phase was separated off and concentrated to about 115 ml of its volume, and the residue was 2-amino-4-difluoro2-amino-4-hydroxy-6-methyl-pyrimidine 25y, chlorotrifluoro, mp 106-107°C. Ethylene 25.6ji, potassium hydroxide 13.8y and dimethylformamide 2
00m19. 8 hours in an autoclave at 6o';
- Stir together. Evaporation of this mixture yields a dark oil. When a small amount of salt precipitate is separated, the melting point is 73-74
2-Amino-4-methyl-6-(1,1,2-)lifluoro-2-chloro-ethoxy)-pyrimidine at °C 8.7
'l Y get.

The final products listed in the table below were obtained by similar means.
0 Formulation example a) Wettable powder a) b) c) Active ingredient 20 g 60 g α5%Na Lignin-sulfonate 5% 5% 54Na
Lauryl sulfate 5 - -N
a Diisobutylnaphthalene-sulfonate -6thioctylphenol-polyethylene glycol ether (elI ethylene 7-8 mol) -2% 2% highly dispersible silica 5% 27% 27% kaolin 67% -- Sodium chloride -59 , 5 active ingredients are thoroughly mixed with the auxiliaries and the mixture is thoroughly milled in a suitable mill. A wettable powder is obtained, which can be diluted with water to obtain a suspension of any desired concentration.

Active ingredients 10% 1% octylph 1-n-polyethylene glycol ether (ethylene oxide 4-5 moles) 5% 3
5%
5% castor oil polyglycol ether (36 moles of ethylene oxide) 4%
4 cyclohexanone 50% 10% thyxylene mixture 50% 79% Emulsions of any desired concentration can be prepared from this concentrate by diluting with water.

C) Powder a) b) Active ingredients (11% 1% talc 99.9% -kaolin
-99% ready-to-use powder,
It is obtained by mixing the active ingredient and the carrier and milling the mixture in a suitable mill.

Active Ingredients 10% 1-Na Lignin-Sulfonate 2% 2% Carboxymethyl Cellulose 1% 1 Thikaolin 87% 96% The active ingredient is mixed with the auxiliaries and the mixture is ground and moistened with water. The mixture is extruded and the extruded material is then dried in a stream of air.

C) Coated Jaw Granules Active Ingredients 3% Polyethylene Glycol (Molecular Weight 200) 3% Kaolin 94% The finely ground active ingredient is applied evenly to the kaolin in a mixer and moistened with polyethylene glycol. thus,
A non-dusting coated granule is obtained.

f) Suspension concentrate a”) b) Active ingredient 40% 5-thiethylene
Glycol 10% 10% Nonylphenol-polyethylene glycol ether (1!II compound ethylene 15 mol) 6%
1% Na lignin-sulfonate
10chi 5% carboxymethyl cellulose
1% 1% 57% formaldehyde aqueous solution
Silicone oil αal in the form of 112% [12% 75% aqueous emulsion/
Homogeneous mixing of the finely ground active ingredient with the auxiliaries yields a suspension concentrate from which suspension concentrates of any desired concentration can be prepared by diluting with water.

g) Salt solution active ingredient 5-isoprobilamide/1% octylphenol-
Polyethylene glycol ether (ethylene oxide 78 moles) 5%
water
91% Biological Example Example 9: Demonstration of herbicidal action before plant germination Seeds of plants are sown in pots 12-15 in diameter in a greenhouse. Immediately thereafter, the soil surface is treated with an aqueous dispersion or solution of the active ingredient. The active ingredient is used at a concentration of 4 Ky/ha. The pots were then placed in a greenhouse at 22-25°C.
temperature and relative humidity of 50-70% [K]. The test was evaluated after 3 weeks and the effect on the test plants was graded according to the following criteria: 1: Plants did not germinate or died completely 2-5: Very strong effect 4-6: Intermediate action 7-8 Two weak actions? = no effect (as untreated control).

Pre-emergence action dosage = active ingredient per hectare 4 to 5 J In the same test format as in Example 9 above, seeds of a larger number of plants are treated with different amounts of the active ingredient.

The studies were evaluated by the same criteria.

Many monocotyledonous and dicotyledonous weeds and cultivated plants are sprayed with aqueous active ingredients at the 4- to 6-leaf stage after germination at a dosage of 4 kg of active ingredient per hectare and then at 24°C.
to 26° and at a relative atmospheric humidity of 45-60%. The test was evaluated 15 days after treatment and the plants were divided into equal numbers according to the same criteria as in the pre-emergence test.

Post-emergence application: 4 Kg of active ingredient per hectare In the same test format as in Example 11 above, a number of plants are treated with different amounts of the active ingredient. The evaluation V& was conducted according to the criteria shown in Example 9 above.

No post-germination action buds! Some commercial potatoes of the Urgenta' strain are washed and dried. These potatoes are then mixed with different concentrations of the active ingredient emullethane.
Soak for 1 minute in each case and subsequently arrange on Okigami paper in a plastic dish and store in the dark for 5 minutes at temperatures of 14° and 21°C.
Maintain at 0° relative atmospheric humidity. Evaluation was performed on the 54th day after application. At the same time, the coulometric loss of the tubers and the weight of the shoots are determined in comparison to the untreated control. In this test, the compounds according to the invention showed complete inhibition of germination. at the same time,
The potato weight loss was less than 10% of the control potato weight loss.

Phosphocarbus palustris (Psopho-ca
rpua palustris) and Centrosema pubesc.
ens) A test plant of Aki from 7 cuttings, soil/peat/
Grow in plastic dishes containing a sand mixture (1:1:1). After the small plants have taken root, add 9cI of this
Transfer to a pot again and add as much water as needed. The plants were placed in a hot water bath at a daytime temperature of 27°C and a nighttime temperature of 21°C.
Further cultivation is carried out with an average irradiation period of 14 hours (6000 lux) and at 70% atmospheric humidity. The test plants were cut to a height of approximately 15oII and then
On day one, a spray solution of active ingredient (calculated as # for 1 hectare of active ingredient a3 or ti3) is sprayed. Four weeks after application, the growth of treated plants is compared to the growth of control plants that were cut but not treated. In this exam, the formula! The plants treated with the active ingredient expressed as A remarkable result was shown that no damage was caused7.

The demonstration test plants were sown in a sandy soil II/Io-mushy arable soil in a plastic container with a capacity of 130 tons, and were washed with a layer of soil IK to a depth of 1-2 crs and washed with water. do. After 1 day, add 500 mg of the active ingredient in the form of an aqueous mist.
It is applied at a violet equivalent to 1/ha and at #degrees equivalent to 60 y/ha and 30 y/ha. The container is then kept in a greenhouse at a temperature of 20-25°C and watered with the required amount. After 53 days, the test is evaluated and the plants are divided into equal numbers according to the same criteria as in Example 9 above.

Pre-emergence active active ingredients in soybean crops 431 1 Bark' soybean seeds are sown in a soil/peat/sand mixture in a ratio of 6:5:j in plastic containers and placed in weather conditioning 1 , warming, illuminance,
By selecting optimal conditions for fertilizer addition and watering, the plants are allowed to develop for about 5 weeks up to the 5-6 trifoliate stage. At this point, plant the ceremony! Spray an aqueous solution of the active ingredient represented by and moisten thoroughly. The evaluation is carried out approximately 5 weeks after application of the active ingredient. According to the present invention, the active ingredient represented by formula
5 ilicles) and 1 dong.

Active ingredient A31 Continued from page 1 Priority claim @April 8, 1982■Switzerland (CH)■
2205782-3

Claims (1)

[Claims] (Eleventh formula ■: (wherein A is a halogen atom, an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms,
C1-C4 alkylsulfinyl group, C1-C4 alkylsulfonyl group, [[
Halogenoalkoxy group with 1 to 4 molecules, 1 carbon atom
C1-C6 alkyl group substituted by a C1-C4 halogenoalkyl group, a C1-C4 halogenoalkylsulfinyl group, or a C1-C4 halogenoalkylsulfonyl group; , or 2 carbon atoms substituted by each of the above groups
Represents 6 to 6 alkenyl groups. E represents a methine group or a nitrogen atom. X represents an oxygen atom, a sulfur atom, or a sulfinyl or sulfonyl bridge. Z represents an oxygen atom or a sulfur atom, m is 1 or 2
The turtle represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or a -Y-R group; the turtle represents a hydrogen atom, a halogen atom, C1-C5 alkyl group, C2-C5 alkenyl group, C1-C4 halogenoalkyl group or -Y-R,, -COOR,. -NO! or -CO-NR, -R represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or an alkyl group having 1 to 4 carbon atoms;
represents an alkyltheo group, a halogenoalkyl group having 1 to 4 carbon atoms, a halogen atom, a halogenoalkoxy group having 1 to 4 carbon atoms, or an alkoxyalkyl group having no more than 4 carbon atoms, and the crest indicates the number of carbon atoms. Y represents a halogenoalkoxy group having 1 to 4 carbon atoms or a halogenoalkylthio group having 1 to 4 carbon atoms; or represents an alkynyl group having 2 to 6 carbon atoms, and each of the above and 1 is independently a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkenyl group having 2 to 5 carbon atoms; 6 to 6 alkynyl groups, and Y represents an oxygen atom, a sulfur atom, or a sulfinyl or sulfonyl bridge, and under the limited condition that X represents an oxygen atom, A is an unsubstituted alkynyl group having 2 to 6 carbon atoms. An alkenyl group χ may also be represented. ) -c-N-7 enylsulfonyl-N'-pyrimidinyl- or -triazinyl-urea, and salts of the compound. (2) The above A is a halogen atom, an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, an alkylsulfinyl group having 1 to 4 carbon atoms, or an alkylsulfonyl group having 1 to 4 carbon atoms. , C1-C4 halogenoalkoxy group, C1-C4 halogenoalkylthio group, C1-C4 halogenoalkoxy group, C1-C4 halogenoalkoxy group, C1-C4 halogenoalkylthio group
represents an alkyl group having 1 to 6 carbon atoms substituted by a halogenoalkylsulfinyl group having 1 to 4 carbon atoms or a halogenoalkylsulfonyl group having 1 to 4 carbon atoms, or 2 carbon atoms substituted by each of the above groups; -6 to 6 alkenyl groups, the above E represents a methine group or a nitrogen atom, the above X represents an oxygen atom, a sulfur atom or a sulfinyl or a sulfonyl bridge, the above Z represents an oxygen atom or a sulfur atom, and the above represents the number 7 with 1 or 2 in the middle, and the above ratio is a hydrogen atom, a halogen atom, an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or -Y-11. represents a group in which the preceding entry is a hydrogen atom, a hydrogen atom, a halogen atom, an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, a halogenoalkyl group having 1 to 4 carbon atoms, or -Y- . C0OR, -NO, or -〇〇-NR, -R, represents a group, where the preceding entry is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a group having 1 carbon atom. represents an alkylthio group having 1 to 4 carbon atoms, a halogenoalkyl group having 1 to 4 carbon atoms, a halogen atom or an alkoxyalkyl group having not more than 4 carbon atoms, and - represents a halogenoalkoxy group having 1 to 4 carbon atoms; , the above-mentioned - and the above-mentioned entry each represent a C1-C5 alkyl group, a C2-C5 alkenyl group or a C2-6 alkynyl group, and the above-mentioned and the above-mentioned - independently of each other represent 1 represents a hydrogen atom, a C1-C5 alkyl group, a C2-C5 alkenyl group or a C2-6 alkynyl group, and the above Y is an oxygen atom, a sulfur atom, or a sulfinyl group; The compound according to claim 1, in which sulfonyl fl' has the following formulas, and under the limiting condition that X represents an oxygen atom, the entry can represent an unsubstituted alkenyl group Y4) having 2 to 6 vertical atoms. , and salts of said compounds. (3) The compound according to claim 1, wherein Z represents an oxygen atom. (4) The compound according to claim 1, wherein the X represents an oxygen atom. (5J) A compound according to claim 1, in which the sum of the number of carbon atoms in the groups - and 9 is greater than 41. (6) Claim 1, in which m represents the number 1.
Compounds described in Section. (7) The compound according to claim 1, wherein said X and said Z represent an oxygen atom, said m represents the number 1, and said group -X-A is present at the 2-position with respect to the sulfonyl group. . (8) The compound according to claim 7, wherein the sum of the number of carbon atoms of the base and the base is not more than 4. (9) The compound according to claim 8, wherein - represents a halogenoethoxy group. 00 The compound according to claim 8, wherein - represents a halogenomethoxy group. I The compound according to claim 9, wherein - represents a 2.2.2-)rifluoroethoxy group. α2 The compound according to claim 10, wherein - represents a difluoromethoxylic group. (13N-(2-difluoromethoxyphenyl-sulfonyl) -N'-(4-methoxy-6-(2,2,2
-trifluoroethoxy)-1,6,5-triazine-
The compound according to claim 1, which is 2-yltuurea. fJa N-(2-difluoromethoxyphenylsulfonyl)-N'-(4-difluoromethoxy-6-
2. The compound according to claim 1, which is methylpyrimidin-2-yl)-urea. a! 9 N-(2-(2-chloroethoxy)-phenyl-sulfurinyl) -N'-(4-methoxy-6-(
Claim 1 which is 2,2,2-)lifluoroethoxy)-1,3,5-triazin-2-yltuurea
Compounds described in Section. HN-(2-)! J fluoromethoxyphenylsulfonyl) -N'-(4-cyfluorome)*-/'-6
-Metel-pyrimidin-2-yl)-urea. Oη The phenylsulfonamide represented by the following formula ■: (In the formula, A, R,, R,, X and m have the meanings defined in the following formula ■.)
, R, , R4 and Z have the meanings defined in the following formula I, and R=t represents a hydrogen atom, a halogen atom, a nitro group or an alkyl group having 1 to 3 carbon atoms. ) with N-pyrimidinyl- or -triazinyl-carbamate of formula I in the presence of a base, optionally converting the product into a salt.
: (wherein A is a halogen atom, an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms,
C1-C4 alkylsulfinyl group, C1-C4 alkylsulfonyl group, C1-C4 halogenoalkoxy group, C1-C4 halogenoalkylthio group, C1-4 The halogenalkylsulfinyl group represents an alkyl group having 1 to 6 carbon atoms substituted by a halogenoalkylsulfonyl group having 1 to 4 carbon atoms, or a halogenoalkylsulfinyl group having 2 to 6 carbon atoms substituted by each of the above-mentioned groups. represents an alkenyl group, E represents a methidi group or a nitrogen atom, x represents an oxygen atom,
Sulfur atom or sulfinyl or sulfonyl bridge Y
Table bl, Z represents an oxygen atom or a sulfur atom, m represents a number of 1 or 2, and RI represents a hydrogen atom, a halogen atom, or a carbon atom number of 1 to 5.
represents an alkyl group having 2 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or a group -Y-R, where - is a hydrogen atom, a halogen atom, an alkyl group having 1 to 5 carbon atoms, a carbon atom number 2
represents a hydrogen atom,
Alkyl group having 1 to 4 carbon atoms, alkoxy group having 1 to 4 carbon atoms, alkylthio group having 1 to 4 carbon atoms, halogenoalkyl group having 1 to 4 carbon atoms,
A halogen atom or a halogenoalkoxy group having 1 to 4 carbon atoms, or an alkoxyalkyl group having not more than 4 carbon atoms, and the tortoise represents a halogen atom or a halogenoalkoxy group having 1 to 4 carbon atoms or a halogenoalkoxy group having 1 to 4 carbon atoms. represents a halogenoalkylthio group, the above - and the above - each represent an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkynyl group having 2 to 6 carbon atoms, the above island and the above - each independently represents a hydrogen atom, a C1-C5 alkyl group, a C2-5 alkenyl group or a C2-6 alkynyl group, and Y is an oxygen atom, a sulfur atom or It represents a sulfinyl or sulfonyl bridge, and under the limiting condition that X represents an oxygen atom, it can also represent an unsubstituted alkenyl group having 2 to 6 carbon atoms. ) A method for producing N-phenylsulfonyl-N'-pyrimidinyl- or -triazinyl-urea. 0 degree formula %! = (In the formula, At R1t~, 4X and Z represent the meanings defined in the following formula!) Phenylsulfonyl isocyanate or isothiocyanate seven-dimensional formula ■: (In the formula, E, R,
and - represent the meaning defined in formula I below. ) with the amine represented by the following formula in the presence or absence of a base, and optionally converted to the product salt: (wherein A is a halogen atom, a carbon an alkoxy group having 1 to 4 atoms, an alkylthio group having 1 to 4 carbon atoms,
a carbon atom substituted by a C1-C4 alkylsulfinyl group, a C1-C4 halogenalkylsulfinyl group or a C1-C4 /% logenoalkylsulfonyl group; Number 1
represents an alkyl group or an alkenyl group having 2 to 6 carbon atoms substituted with each of the above groups, E represents a methine group or a nitrogen atom χ, X represents an oxygen atom,
Sulfur atom or sulfinyl or sulfonyl bridge'
, Z represents an oxygen atom or 7 sulfur atoms, m represents a number Y of 1 or 2, and electron represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 5 carbon atoms, or an alkenyl group having 2 to 5 carbon atoms. or -Y-- group Y: represents a hydrogen atom, ) ~ rogene atom, an alkyl group having 1 to 5 carbon atoms, 2 carbon atoms
-C5 alkenyl group, C1 -C4 halogenoalkyl group or -Y -R,, -COOR,. -NO! or -CO-NRF-4 group, - represents a hydrogen atom, a C1-C4 alkyl group, a C1-C4 alkoxy group, a C1-C4 alkoxy group,
alkylthio group, C1-C4/% logenoalkyl group, halogen atom or C1-4
represents a halogenoalkoxy group having more than 4 carbon atoms, or an alkoxyalkyl group having more than 4 carbon atoms, and d represents a halogenoalkoxy group having 1 to 4 carbon atoms or a halogenoalkyl theo group having 1 to 40 carbon atoms.
a', the above-mentioned 穓 and the above-mentioned islands each represent a C1-C5 alkyl group, a C2-5 alkenyl group, or a C2-6 alkynyl group, and the above-mentioned horses and the above-mentioned islands are mutually independently represents a hydrogen atom, a C1 to C5 alkyl group, a C2 to C5 alkenyl group or a C2 to C5 alkynyl group, and Y is an oxygen atom, a sulfur atom or a sulfinyl group; sulfonyl bridge, and under the limiting condition that X represents an oxygen atom, said group may also represent an unsubstituted alkenyl radical having 2 to 6 carbon atoms. ) Te surface sales Z:, N-, phenylsulfonyl-N'
A method for producing -pyrimidinyl- or -triazinyl-urea. 0 Formula l: (In the formula, -A, R1p a, e x and m are the following formulas!
to destroy the meaning defined by ) phenylsul7onamide represented by the following (in the formula,
E, R, , R4 and Z have the meanings defined in formula I below. ) with an incyanate or isodeocyanate of the following formula I: m (wherein A is a halogen atom, an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms,
C 1 -C 4 alkylsulfinyl group, carbon I
AHI child* 1 alkylsulfonyl group of sulfur 4,
substituted with a halogenoalkoxy group having 1 to 4 carbon atoms, a halogenoalkylthio group having 1 to 4 carbon atoms, a halogenoalkylsulfinyl group having 1 to 4 carbon atoms, or a halogenoalkylsulfinyl group having 1 to 4 carbon atoms; represents an alkyl group having 1 to 6 carbon atoms or substituted by each of the above-mentioned groups! 6 represents an alkenyl group, E represents a methine group or a nitrogen atom, X represents an oxygen atom,
represents a sulfur atom or a sulfinyl or sulfonyl bridge; Z represents an oxygen atom or multiple sulfur atoms; m represents a number of 1 or 2; Peng represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or a -Y-9 group, and R4 is a hydrogen atom, a halogen atom, or a C1 to 5 alkyl group; an alkyl group, a C2-C5 alkenyl group, a C1-C4 halogenoalkyl group or -Y-R,, -COOR,. -No snow or -CO-N represents a group, - is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, C 1 -C 4 halogenoalkyl, halogen or C 1 -C 4 halogenoalkoxy, or alkoxyalkyl with more than 4 carbon atoms, - means C 1 -4 represents a halogenoalkoxy group or a halogenoalkylthio group having 1 to 4 carbon atoms, and the above - and the above - each represent an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or a halogenoalkylthio group having 2 to 5 carbon atoms. 6 represents an alkynyl group, and the above and the above - independently represent a hydrogen atom, a C1 to C5 alkyl group, a C2 to C5 alkenyl group, or a C2 to C6 alkynyl group. N-7 represented by Enilsulfoyu,! / -N'-
A method for producing pyrimidinyl- or -triazinyl-urea. (4) The following formula (2) (wherein A, R1g, and X represent the meanings defined in the following formula I, and R11 is a hydrogen atom, a halogen atom, a nitro group, or a carbon atom number of N-phenylsulfonyl carbamate represented by the following formula ■: (where E, l (and K represent the meanings defined in the following formula ■)) and, optionally,
t(X-A)m (wherein A is a halogen atom, an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms,
C1-C4 alkylsulfinyl group, carbon W
Alkylsulfonyl group with AR atoms t11 to 4, halogenoakoxy group having 1 to 4 carbon atoms, /10 genoalkylteo group having 1 to 4 carbon atoms, 1 carbon atom
to 4)-logenoalkylsulfinyl group or a C1 to C6 alkyl group substituted by a C1 to C4 halogenoalkylsulfinyl group, or substituted by each of the above groups. represents an alkenyl group having 2 to 6 carbon atoms, and E is a methine group or a nitrogen atom 'kf! and X represents an oxygen atom, a sulfur atom, or a sulfinyl or sulfonyl bridge. Z represents an oxygen atom or a sulfur atom, m is 1 or 2
R3 represents a hydrogen atom, a halogen atom, or a carbon atom number of 1 to 5.
' represents an alkyl group having 2 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or a group -Y-R, where the island represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 5 carbon atoms, or a group having 2 to 5 carbon atoms. alkenyl group, C1-C4 halogenoalkyl group or -Y-R,,-COOI%. -No snow or -Co-N to -R$ group, - represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms , represents a C1 to C40 logenoalkyl group, a halogen atom or a C1 to C4 halogenoalkoxy group, or an alkoxyalkyl group having no more than 4 carbon atoms, - represents a C1 to C40 alkoxy group; 4 represents a halogenoalkoxy group or a halogenoalkylthio group having 1 to 4 carbon atoms, and each of the above and the above represents an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or a halogenoalkylthio group having 1 to 4 carbon atoms. represents an alkynyl group having 2 to 6 carbon atoms, and the above - and the above - independently represent a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkynyl group having 2 to 6 carbon atoms. ytab, and said Y represents an oxygen atom, a sulfur atom, or a sulfinyl or sulfonyl bridge 1', and under the limiting condition that said X replaces an oxygen atom, said person represents an unsubstituted alkenyl group having 2 to 6 carbon atoms. t can also be destroyed. ) A method for producing N-phenylsulfonyl-N'-pyrimidinyl- or -triazinyl-urea. ? 2) The urea derivative represented by formula I, caremin, is reacted with an alkali metal or alkaline earth metal hydroxide or a quaternary ammonium base to obtain an addition salt according to claims 15 to 18. The manufacturing method according to any one of the above.(b) In addition to a carrier and/or other auxiliary agents, the active ingredient may contain the following formula: to 4 alkylthio groups,
C1-C4 alkylsulfinyl group, C1-C4 alkylsulfonyl group, C1-C4 halogenoalkoxy group, C1-C4 halogenoalkylthio group, C1-4 C 1 -C 6 alkyl group substituted by a halogenoalkylsulfinyl group or a C 1 -C 4 halogenoalkylsulfinyl group, or a C 2 -C 6 alkenyl group substituted by each of the above groups; E represents a methine group or a nitrogen atom, X represents an oxygen atom, a sulfur atom, or a sulfinyl or sulfonyl bridge, Z represents an oxygen atom or a sulfur atom, m represents 1 or 2
R represents a hydrogen atom, a halogen atom, and a carbon atom number of 1 to 5.
represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms; , C1-C4 halogenoalkyl group or -Y-Rs, -COOR,
. -No Goose or -Co-NR? -- represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 11 to 41 carbon atoms, an anylkylthio group having 1 to 4 carbon atoms, or a halogenoalkyl group having 1 to 4 carbon atoms. represents a halogen atom, a halogenoalkoxy group having 1 to 4 carbon atoms, or an alkoxyalkyl group having not more than 4 carbon atoms, - is a halogenoalkoxy group having 1 to 4 carbon atoms, and 9 is a carbon atom. Halogenoalkylthio group t of numbers 1 to 4
ll! ! I, Said and Said - each represent a C1-C5 alkyl group, a C2-C5Q7-rukenyl group or a C2-C6 alkynyl group; and a hydrogen atom, a C1-C5 alkyl group, a C2-C5 alkenyl group or a C2-6 alkynyl group y! - and the Y is an oxygen atom, a sulfur atom, or a sulfinyl or sulfonyl bridge? Furthermore, under the limiting condition that X represents an oxygen atom, A may also represent an unsubstituted alkenyl group t having 2 to 6 carbon atoms. ) A herbicidal and plant growth inhibitor containing at least one type of N-phenylsulfonyl-N'-pyrimidinyl- or -triazinyl-urea represented by VS*. (2) The composition according to claim 22 for inhibiting undesirable plant growth. (c) Claim 2 for suppressing plant growth
Composition according to item 2. (c) The composition according to claim 23 for selectively controlling weeds in useful crops before or after germination. (to) The composition according to claim 25, wherein the useful crops are grains, corn, rice, and cotton. 26. The composition according to claim 25, wherein the useful crop is dice. (2) A composition according to claim 24 for inhibiting plant growth beyond the two-leaf stage Y, which comprises using the active ingredient by pre-emergence means. (2) The composition according to claim 22 for regulating the growth of useful crops for the purpose of increasing yield. (To) Claim 2, wherein the useful crop is dice.
Composition according to item 9. o9 The composition according to claim 24, wherein the useful plant is a legume.