JPS5973583A - N-pyridylsulfonyl-n'-pyrimidinylurea or n-pyridylsulfonyl-n'-triazinylurea, manufacture and herbicidal and plant growth regulant composition - 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-
Pyridylsulfonyl-■-pyrimidinyl urea and (J N
- Concerning hyridylsulfonyl-N'-triazinyl ureas, processes for their preparation, compositions containing them and their use, in particular for selective weed control or for the regulation and suppression of plant growth, in plantings of beneficial plants. .

The N-pyridylmelphonyl-N'-pyrimidinyl urea and N-pyridylsulfonyl-N'-triazinyl urea and salts thereof of the present invention have the following formula I; atom, alkoxy group having 1 to 4 carbon atoms, alkylthio group having 1 to 4 carbon atoms, alkylsulfinyl group having 1 to 4 carbon atoms, alkylsulfonyl group having 1 to 4 carbon atoms, carbon atom Haloalkoxy group having 1 to 4 carbon atoms, haloalkylthio group having 1 to 4 carbon atoms, haloalkylsulfinyl group having 1 to 4 carbon atoms, or haloalkylsulfinyl group having 1 to 4 carbon atoms
C 1 -C 6 alkyl substituted by C 1 -C 6 alkyl, which is substituted by C 1 -C 6 alkyl or C 2 -C 6 alkyl, which is unsubstituted or substituted with the same substituents as C 1 -C 6 alkyl; f or unsubstituted halogen, cyano, nitro, C1 -C4 alkyl, C1 -C4 haloalkyl, -X- 1-4-Alkyl group, C1 -C4 alkoxycarbonyl group, amino group, mono- or di-(C1-C4 alkyl) amino group, carbamoyl group, mono- or di-(C1 -C4 alkyl) group, represents a phenyl group substituted with a mono- or C(alkyl having 1 to 4 carbon atoms) carbamoyl group, a sulfamoyl group, a sulfamoyl group (alkyl having 1 to 4 carbon atoms), or a phenyl group substituted with a famoyl group, or A-X- is an amino group- N 几, R ri are formed, E represents a methine group or a nitrogen atom, and R is a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, carbon Haloalkyl group having 1 to 4 atoms, haloalkoxy group having 1 to 4 carbon atoms, alkoxyalkoxy group having 2 to 5 carbon atoms,
γ-alkylthio group having 1 to 5 carbon atoms, 1 carbon atom
-5 alkylsulfinyl group or 1 carbon atom
It represents an alkylsulfonyl group having 1 to 5 carbon atoms, and represents an alkyl group having 1 to 3 carbon atoms or an alkoxy group having 1 to 3 carbon atoms, which is unsubstituted or substituted with 1 to 3 710 atoms. Bird is a hydrogen atom, a halogen atom, an amino group -NR4 mass or an alkyl group having 171 to 3 carbon atoms, which is unsubstituted or substituted with 1 to 3 halogen atoms, which is not yet substituted or represents a methoxy group, an ethoxy group, or an alkoxy group having 1 to 4 carbon atoms substituted with 1 to 6 halogen atoms, R4 represents a hydrogen atom or a methyl group, and R5 represents a hydrogen atom or a carbon atom number of 1 to 2 represents an alkyl group or a methoxy group, R6 and H each independently represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkenyl group having 5 to 5 carbon atoms, an alkynyl group having 5 to 5 carbon atoms, It represents an alkoxyalkyl group having 3 to 6 carbon atoms, a cyanoalkyl group having 1 to 4 carbon atoms, or, together with the nitrogen atom to which both are bonded, contains an oxygen atom, a sulfur atom, or a ring member. also forms a saturated 5- or 6-membered heterocycle which can also contain -Ni1.8 groups, avian is a hydrogen atom, a C1-C4 alkyl group or a benzyl group, and , X represents an oxygen atom, a sulfur atom, a sulfinyl fur group, or a sulfonyl bridge, provided that -X-A is an alkenyl sulfide group having 3 to 4 carbon atoms, an alkenyl sulfinyl group having 3 to 4 carbon atoms, or a carbon atom represents an alkenylsulfonyl group of number 3 or 4,
If R simultaneously represents a hydrogen atom, a halogen atom, a methyl group, a methoxy group, a trifluoromethyl group, a nitro group, a cyanide group, or a methoxymethyl group, the substituent is an argyl group having 1 to 2 carbon atoms. C 1 -C 2 alkoxy or methoxymethyl, and R3 is limited to methyl or methoxy. ) Urea, triazine and pyrimidine which are effective as leather removers are generally known to those skilled in the art. Pyridylsulfamoyl-heterocyclic-aminocarbamoyl compounds having herbicidal and plant growth regulating activities have recently been developed. , for example in European Patent Application Nos. 13480 and 55895.

In the above multilayer, the alkyl group is a straight chain and 5 is a branched alkyl group, such as methyl group, ethyl group, n
-Propyl group, inpropyl group, four types of isomers of butyl group, n-amyl group, inamyl group, 2-amyl group, 3-
It means an amyl group, n-hexyl group or isohexyl group.

The alkoxy group means four types of isomers: methoxy group, ethoxy group, n-propoxy group, impropoxy group, and butoxy group, and examples of the alkylthio group are preferably memethoxy group, ethoxy group, or isopropoxy group. Examples include methylthio group, ethylthio group, n-propylthio group, isopropylthio group, and n-butylthio group, with methylthio group and ethylthio group being preferred.

Examples of alkenyl groups include vinyl, allyl, impropenyl, propen-1-yl, buten-1-yl, buten-2-yl, buten-3-yl, and isobutyn-1-yl. , isobutyn-2-yl group, penten-1-yl group, penten-2-yl group, penten-3-yl group
yl group, henten-4-yl group or hexenyl isomer, with nyl group, allyl group and penten-4-yl group being preferred for bi4.

Examples of alkylsulfinyl groups include methylsulfinyl group, ethylsulfinyl group, and n-7'.

There is a pyrsulfinyl group or an n-butylsulfinyl group. Preferred are methylsulfinyl group and ethylsulfinyl group.

Halogen atoms and haloalkyl groups in the above definitions,
Part of haloalkoxy group and haloalkylthio group! ~
The halogen atoms are fluorine atoms, chlorine atoms and bromine atoms, preferably fluorine atoms and chlorine atoms.

Therefore, a haloalkyl group or a haloalkyl group as part of a substituent defined in item 1.t: chloromethyl group,
Fluoromethyl group, difluoromethyl group, trifluoromethyl group, 2-chloroethyl group, 21292-) trifluoroethyl group, 's't2t2-tetrafluoroethyl group, pentafluoroethyl group, 1,1.2-trifluoro- 2-chloroethyl group, 2,2.2-) IJ fluoro7-1.1-dichloroethyl group, pentachloroethyl group,
5,3.5-)lifluoroproyl group, 2,5-diq. It is understood to include rozolopyl, 1,1,2,3,3,3-hexafluoropropyl, with chloromethyl, difluoromethyl and trifluoromethyl being preferred.

In the above definition, alkynyl groups generally include propargyl, butyn-2-yl, butyn-3-yl groups and isomers of pentynyl and hexanyl groups. However, preferred alkynyl groups are propargyl, butyne-
The 2-yl group is still a butyn-3-yl group.

The present invention also includes salts which the compounds of formula 1 can form with amines, alkali metal bases, alkaline earth metal bases or quaternary ammonium bases. The metal hydroxides are lithium hydroxide, sodium hydroxide, potassium hydroxide, magnesium hydroxide and calcium hydroxide, most preferably lithium hydroxide and potassium hydroxide.

Examples of amines suitable for forming salts include methylamine, ethylamine-propylamine, isopropylamine, the four isomers of butylamine, dimethylamine, diethylamine, jetanolamine, dipropylamine, diisopropylamine, di- n-butylamine,
There are primary, secondary and tertiary aliphatic and aromatic amines such as pyrrolidine, piperidine, morpholine, trimethylamine, triethylamine, tripropylamine, ginuclidine, pyridine, quinoline, and inquinoline. Preferred amines are ethylamine, propylamine, diethylamine and triethylamine, with isopropylamine and jetanolamine being most preferred.

Examples of quaternary ammonium bases generally include haloammonium cations such as tetramethylammonium cation, trimethylbenzylammonium cation, triethyl41) benzylammonium cation, tetraethylammonium cation, trimethylethylammonium cation, and ammonium cation. Of the compounds of formula I with a salt cation, preferred are O a) where RQ represents a hydrogen atom, b) where R represents a hydrogen atom and X represents an oxygen atom or a sulfur atom. C) A compound represented by the following formula: d) A compound represented by the above formula, in which X represents an oxygen atom; e) N-pyridylsulfonyl-N'-pyrimidinyl represented by the following formula: urea, f) N-pyridylsulfony A, -N'-)riazinyl urea, represented by the following formula: (wherein A' is an alkenyl group having 6 to 4 carbon atoms or a carbon atom) (Represents an alkoxyalkyl group of the number 3 to 4.) In the above formula, A, E, R, R2, bird and X have the same meanings as defined in formula (■) A final method for obtaining compounds of formula I is carried out in an inert organic solvent.

A first method for obtaining N-pyridylsulfonyl-N'-pyrimidinyl urea or N-pyridylsulfonyl-N'-triazinyl urea of formula I is as follows: The pyridylsulfonamide represented by the following formula m = 1, which has the same meaning as defined in the formula ■, is the formula m = 1. In the formula, Tori, Tori, and E are the formula! It has the same meaning as defined above, and represents a phenyl group or a phenyl group substituted with a halogen atom or an alkyl group. ) N-pyrimidinyl carbamate or N-
) consists of reacting with riazinyl carbamate in the presence of a base.

A second method for obtaining N-pyridylsulfonyl-N'-pyrimidinylurea or N-pyridylsulfonyl-N'-triazinylurea of formula 1 is as follows: Expresses the same meaning as defined in formula ■. ) 5;3 2 Pyridylsulfonylinocyanate represented by the following formula V: In the formula, E, bird and bird represent the same meanings as defined in formula I. ) and optionally in the presence of a base.

A third method for obtaining N-pyridylsulfonyl-N'-pyrimidinylurea or N-pyridylsulfonyl-N'-triazinylurea represented by formula i is the following formula (■): (wherein RQ is a phenyl group or a halogen Represents a phenyl group, an alkyl group having 14 to 4 carbon atoms, or an alkoxyalkyl group having 2 to 8 carbon atoms substituted with an atom or an alkyl group having 1 to 4 carbon atoms. represents an atom, and A, H,.

and X have the same meanings as defined in formula I. ) with an amine of formula V in the presence of an acid acceptor and a base of 17. If desired, the urea of formula I can be It can be converted into addition salts with amines, alkali metal hydroxides or alkaline earth metal hydroxides, or addition salts with quaternary ammonium bases. This transformation can be carried out, for example, by reacting a compound of formula l with the same molar amount of base and evaporating off the solvent. The starting materials of formulas U, lv and ■ are new compounds. These compounds The pyridyl sulfonamide represented by the formula (2) is prepared by diazotizing a suitably substituted pyridylamine, and in the presence of a catalyst such as copper mine chloride, Hydrochloric acid can be obtained by replacing the diazo group with sulfur dioxide in acetic acid and reacting the resulting pyridylsulfonyl chloride with ammonia. The corresponding pyridylamines are known or can be prepared by known methods. In special cases, for example when activated substitution positions are available, direct chlorosulfonation of the pyridine ring is possible, giving the corresponding pyridylsulfonyl chloride by reaction with excess chlorosulfonic acid. A similar reaction for alkoxyanilides has been reported in European Patent Application No. 44807.
It is stated in the specification of the No.

Pyridylsulfonamide represented by 2■ is also published in the Journal of Medical Chemistry (J@Med Lu Che
m*) Vol. 25, p. 1376 (1980), which consists in chlorinating suitably substituted mercaptopyridines with chlorine gas in aqueous solution. The pyridyl 5(' sulfonyl chloride thus obtained is reacted with ammonia to give pyridyl sulfonamide.

French Pharmaceutical Society Journal (Ann@Pharm-Fr-) No. 5
By using a modification of the method described in Vol. 1, p. 467 (1975), a suitably substituted pyridine ring can be prepared by
if desired in an inert solvent, first by fuming sulfurization and then by treatment with phosphorus pentachloride to give the pyridylsulfonyl chloride;
Then, it can be reacted with ammonia to obtain a pyridylsulfonamide represented by the formula (2).

A novel pyridylsulfonamide represented by the formula (2) is also prepared by combining a pyridylsulfonamide halogenated at an appropriate position with an alcohol, a thiolmatahasulfinyl or a kesulfonyl compound in the following formula: In the formula 1, A , R, and X have the same meanings as defined 1- in formula I. ) can be obtained by reacting according to Details of such reactions can be found in the Journal of the Belgian Pharmaceutical Society (J*P
harm, Be Igo) Volume 35, Page 98 (19
80).

The novel pyridyl sulfonamide represented by the formula... can be further prepared by combining hydroxypyridyl sulfonamide with mercaptopyridyl sulfonamitra, a halogen compound in the presence of an inert solvent and a base as an acid acceptor, and a halogen compound of the following formula: C, where A , R, and X have the same meanings as defined in formula (2), and Ha 1 represents a halogen atom, particularly a chlorine atom or a bromine atom. ) can be obtained from older sister by reacting according to the following. Such reactions are described, for example, in published European Patent Application No. 4480
It is described in the specification of No. 7.

Pyridylsulfonamides in which X represents a sulfonyl group or a sulfonyl bridge can be obtained by oxidation of the corresponding thiol compounds. Such oxidations are described, for example, in published European Patent Application No. 55,895.

The sulfonyl isocyanate represented by the formula (2) can be obtained by phosgenating the sulfonamide represented by the formula (2) in the presence of butyl isocyanate in a chlorinated hydrocarbon in a solvent at its reflux temperature. A similar reaction is a new method of manufacturing organic chemistry (New Meth).
ods of Pre-parative Organ
ic Chemistry), Volume 6, pp. 223-241, Academic Press (Academic
Press), 2:1--York and London.

Pyridylsulfonyl carbamate represented by formula
9 by reacting with tomato or phenyl chloroformate in the presence of a base. A similar reaction is reported in Japanese Patent No. 611.
It is described in the specification of No. 69.

Aminopyrimidines and aminotriazines of formula V used as starting materials and the corresponding aminopyrimidines and aminotriazines of formula 1
The phenyl carbamates represented by are either well known or disclosed in Swiss patent application no.
No. 8, or can be produced from the compounds described above by known methods.

The reaction to obtain the compound represented by formula (■) is carried out using a neutral inert organic solvent such as methylene chloride, tetrahydrofuran,
It is advantageous to carry out ('f) in acetonitrile, dioxane or toluene.The reaction temperature is -20°-+120°.
A range of 0.degree. C. is preferred.

The reaction is usually slightly exothermic and can be carried out at room temperature. In order to shorten the reaction time and also to start the reaction, it is advantageous to heat the reaction mixture briefly to the boiling point.The reaction time can also be shortened by adding a few drops of base or incyanate as a catalyst.

O The final product can be obtained by concentrating the reaction mixture and/or removing the solvent by evaporation and recrystallizing the solid residue in less soluble solutions such as ethers, aromatic hydrocarbons and chlorinated hydrocarbons. It can be separated by crushing.

The compound represented by formula (1) is a stable compound and does not require any protective measures in handling.

When used at low application rates, the compounds of formula I have good selective growth control and selective herbicidal properties.
This means that the compound can be used in 1-use of useful plants, especially cereals.
It will show excellent utility in the cultivation of cotton, dice, corn and rice. In some cases, traditionally
It can also damage weeds that could only be affected by non-selective herbicides. The mode of action of this compound is unique. Many of the nuclear compounds are mobile, i.e. they cannot be absorbed by plants. It then migrates to other parts of the plant and develops its effects there. Therefore, for example, by applying it to the surface of perennial weeds, it is possible to damage even the roots. In comparison to other herbicides and growth regulators, the novel compounds of formula I work even when applied at very low application rates.

In addition, the compound represented by formula ■ exhibits significant growth regulation,
It has particularly growth inhibiting properties. The growth of both monocots and dicots is inhibited. Therefore, for example, the growth of legumes, which are often planted as intercrops in the tropics, can be selectively inhibited by the compound represented by Er formula 1. When applied at a higher rate, which can prevent soil erosion between cultivated crops while also reducing competition between intercrops and cultivated crops, all test plants were significantly affected at their developmental stage. It becomes damaged and dies.

The present invention also provides herbicidal and growth regulating compositions containing the novel compounds of formula I, as well as methods for the pre- and post-emergence control of weeds, and monocotyledonous and dicotyledonous plants, particularly weeds, tropical intercrops and This invention relates to a method for suppressing the growth of tobacco plant suckers.

The compounds of formula i are still used in their it form, preferably together with the auxiliaries customary in formulation technology and are therefore prepared in known manner, for example in emulsion concentrates, coatings, etc. Stone processed into a paste, a directly sprayable or dilutable solution, a diluted emulsion, an aqueous solution, a soluble powder, a powder, a granule or a composition encapsulated, for example, in a polymeric substance. Depending on the nature of the composition, the method of application, for example spraying, jetting, scattering, scattering or pouring, is selected depending on the purpose and the given environment.

Formulations, i.e. compositions, preparations or compounds, comprising the active ingredient of formula I and optionally solid or liquid excipients can be prepared in a known manner, e.g. by combining the active ingredient with fillers such as solvents, solid carriers and Optionally prepared by homogeneous mixing and/or grinding with surface-active compounds (surfactants) □6: The suitable solvent is an aromatic hydrocarbon, preferably 8 to 12
For example, xylene mixtures or substituted naphthalenes, phthalate esters such as dibutyl phthalate or dioctyl phthalate, cyclohexanone fr are aliphatic hydrocarbons such as paraffins, ethanol, ethylene glycol, ethylene glycol monomethyl ether or mono Alcohols such as ethyl ether, glycols and their ethers and esters, ketones such as cyclohexanone, N-methyl-2-pyrrolidone, dimethyl sulfoxide, strongly polar solvents such as dimethylformamide: as well as epoxidized coconut oil or Epoxidized vegetable oil such as soybean oil; or water.

The solid carriers used for example for dusts and dispersible powders are the usual mineral fillers such as calcite, talc, kaolin, montmorillonite or attapulgite.To improve the physical properties , shoulder-dispersed silicic acid or highly dispersed adsorptive polymers can also be added.

Suitable granular adsorptive carriers are porous, for example pumice, crushed brick, sepiolite or bentonite; suitable non-adsorptive carriers are materials such as calcite or sand. Furthermore, a very large number of inorganic or organic pre-granulated substances can be used, such as in particular dolomite or plant residue powder.

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. The term electrosurfactant l is also understood to include mixtures of surfactants.

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

5 Suitable soaps are alkali metal salts, alkaline earth metal salts or unsubstituted or substituted ammonium salts of higher fatty acids (CIOC 22), such as the sodium salts of oleic acid or stearic acid or natural fatty acid mixtures obtained from e.g. coconut oil or tallow. or potassium salts. Fatty acid methyllauric salts may also be mentioned.

However, more frequently so-called synthetic surfactants are used, especially fatty sulfonates, fatty sulfates, sulfonated benzimidazole derivatives or alkylaryl sulfonates.

Fatty sulfonates or sulfates are usually in the form of alkali salts, alkaline earth metal salts or unsubstituted or substituted ammonium salts, containing from 8 to 22 carbon atoms and also containing the alkyl part of the acyl group. Those with an alkyl group,
namely sodium or calcium salts of lignosulfonic acid, dodecyl sulfate or fatty alcohol sulfates obtained from natural fatty acids. These compounds also include sulfuric esters of aliphatic alcohol 6/ethylene oxide and
Also includes salts of acid. Sulfonated benzimidazole derivatives have two sulfonic acid groups and 8 to 22 carbon atoms.
Those containing one fatty acid group are preferred. An example of an alkylaryl sulfonate is naphthalene sulfone! / Sodium, calcium or triethanolamine salts of formaldehyde condensates. Mention may also be made of the abovementioned salts of the phosphoric acid esters of p-nonylphenol and adducts of 4 to 14 mol of ethylene oxide or phospholipids.

Preferred nonionic surfactants are polyglycol ether derivatives of aliphatic or cycloaliphatic alcohols or/saturated or unsaturated orofatty acids and alkylphenols, which have 3 to 30 glycol ether groups (fatty or Group) having 8 to 20 carbon atoms in the hydrocarbon moiety and 6 to 18 carbon atoms in the alkyl moiety of the alkylphenol.

0) Further suitable nonionic surfactants include polyethylene oxide, polypropylene glycol, ethylenediamine polyglopylene glycol, and 1 to 1 surfactants in the alkyl chain.
Water-soluble adducts of alkyl polyglobylene glycols having 0 carbon atoms and having 10 to 250 ethylene glycol ether groups and 10 to 100 propylene glycol ether groups. These compounds usually contain 1 to 5 diglycol units per propylene glycol unit.

Typical examples of nonionic surfactants are nonylphenol polyethoxyethanol, castor oil polyglycol ether,
Polypropylene/polyethylene oxide adduct, tributylphenoxypolyethoxyethanol, polyethylene glycol and octylphenoxyethoxyethanol. Aliphatic esters of polyoxyethylene sorbitan and polyoxyethylene sorbitan trioleate are also suitable nonionic surfactants. Cationic surfactants are surfactants containing at least one carbon atom as an N-substituent. Quaternary ammonium salts containing 22 alkyl groups and preferably lower unsubstituted or halogenated alkyl, benzyl or lower hydroxide alkyl groups as N-substituents are preferred. These salts are in the form of halides, methyl sulfate or ethyl sulfate, such as stearyltrimethylammonium chloride or benzyl di(
2-chloroethyl)ethylammonium bromide is preferred.

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

“MC Cutcheon’s Annual Report on Detergents and Emulsifiers (M
cCuLcheods Detergents and
kinuls4fjersAnnua I)s, MC Publishers, Ringwood (1 also jngwood)
= , :L-Chassis, 1979;
isely), l=- and Wood, "Encyclopedia of Surfactants"
rface Ac11ve, Agents)'', Kagaku Publishing, New York, 1964C!] The compositions of the present invention generally contain the compound of formula I in an amount of 0.1 to 95%, preferably 0.1 to 80%, solids. Or it contains 1 to 999% of a liquid auxiliary agent and 25% to 25% of a surfactant, preferably 0.1 to 25%.

Particularly preferred formulations are those consisting of the following composition (excellent = weight percentage): Emulsion concentrate active ingredient = 1 to 20q6, preferably 5 to 10
% surfactant: 5 to 30%, preferably 10 to 2
0% liquid carrier: 50 to 94%, preferably 70 to 8
5 Powder active ingredient 20.1 to 10%, preferably 01 to 1% Support carrier 2999 to 90%, preferably 999 to 290% Suspension concentrate active ingredient: 5 to 75%, Preferably 10 to 50
% water = 94 to 25%, preferably 90 to 30
% surfactant = 1 to 40, preferably 2 to 30
% Irrigation active ingredient = 0.5 to 90%, preferably 10 to 80% Surfactant = 0.5 to 20%, preferably 1 to 1
5% Solid support: 5 to 95%, preferably 15 to 90
% Granule active ingredient 20.5 to 30%, preferably 5 to 1
5% 161 body carrier: 995 to 70%, preferably 97 to 85 cm, iso-thick compositions are preferred as commercial products, whereas 1 end consumers generally use diluted compositions. The formulation may be diluted to 0.001% active ingredient. Application rates are generally between 0.01 and 10 active ingredients per hectare.
- preferably 0.025 to 5 kf.

The composition may further include other ingredients such as stabilizers, anti-foaming agents,
Viscosity modifiers, binders, thickeners, chickpea fertilizers and other compounds for obtaining special tanofruit can be included.

The invention is illustrated by the following examples.

Example 1 I'J -(2-(2-methoxyethoxy)-5-pyridylsulfonyl)-N-[4-methoxy-
6-methyl-1,! Preparation of 1.5-triazin-2-yl]urine 2.

5.2f'i,
Anhydrous dioxane 50ml! Medium, 2-(2-methoxy)-
3-Pyridylsulfonamide 4.649 and 1,8-diazabicyclo[5,4,0)-undec-7-nin 61-
at a maximum temperature of 22°C. The mixture was stirred at room temperature for 1 h, concentrated in vacuo, and the residue was purified with 2N HCl.
I aqueous solution 12#I/! Stir in a bowl and mix well. The residue is washed with water and dried to obtain urea 7.9f having a melting point of 112° to 114°C.

The starting vD negative 2-(2-methoxyethoxy)-3-pyridylsulfonamide is prepared as follows: Sodium/previous 55% dispersion in 4.36 ft. methyl cellosolve 251 nll/C in a stream of nitrogen. Approximately 15 bolts each
Add in portions. Next, 2-
A solution of chloro-3-pyridylsulfonamide 9.67 was added to the above dispersion for 5 minutes with stirring. The reaction mixture is then stirred for 1 hour at reflux temperature and concentrated in vacuo. The residue was acidified to f'j-12 with aqueous hydrochloric acid solution of about 25° C. at a temperature below 15° C., then stirred and filtered to give the desired 2-(2-methoxy-ethoxy)-6- Pyridyl≠≠Sulfonamide 11. ! It was obtained and recrystallized from acetonitrile and has a melting point of 102°-103°C.

Example 2 N-[2-dimethylamino-3-pyridylsulfonyl)-N-(4-methoxy-6-methyl-1-
1,3,5-triazin-2-yl] urine accumulation! ! 8! 0 N-(4-methoxy-6-methyl-1,3,,5-)riazin-2-yl)phenylcarbame-), 5.2El
2-dimethylamine-5 in anhydrous dioxane 50-
-pyridylsulfonamide 2:41f and 1,7-1 diazabiscif O[S, 4°0] undec-7-nin 1
．． Add 9 ml to the mixture at room temperature 1. Add the mixture to this? Stir for 1 hour under a sieve, and then pour the mixture into an empty container. Stir the residue in a 1N water fountain solution and wash in a fan. Urea 3942 with a melting point of 173°-175°C when dried
I can cum.

The starting η′-membered 2-dimethylamine-5-pyridylsulfonamide is prepared as follows: in a pressure reactor containing 673f of 2-chloro-5-pyridylsulfonamide in 60ml of anhydrous tetrahydrofuran. Dimethylamine 632 is heated at 0°C. The contents of the reactor are stirred at 60°C for 75 minutes, then cooled and filtered.Vt
The liquid was concentrated in vacuo and the residue was stirred in a 1:1 mixture of ether/petroleum ether and filtered by ip, mp 98°-
Incubate the sulfonamide 632f at 100°C.

Examples N-[2-phenoxy-5-pyridylsulfonyl)-N-(4-methoxy-6-meth-1.5.
5-) Production of riazin-2-yl]urea.

a) N-(4-methoxy-6- Methyl-1,3,5
-) riazin-2-yl) phenylcarbame) 2.0
Incubate El at 25°C. The mixture was stirred at room temperature for 20 hours, then poured into a mixture of 150 ml of hydrochloric acid and ice. lF
The precipitate is completely separated by filtration, washed with water, dried, and crystallized from αμ-free ethyl. Preferably, urea 2y with a melting point of 181°-182°C is 2-phenoxy. 3-Pyridylsulfonamide is prepared as follows: b) To a solution of phenol 2072 in 150 ml of dimethyl sulfoxide 14 ml of K (Jl-1 powder (88≠)) is added and the mixture is stirred for 1.5 h. Stir. Next, a solution of 19.26 f of 2-chloro-5-pyridylsulfonamide in 50 nr1 of dimethyl sulfoxide and 18-crown-60,1
Add F and continue stirring at 150° C. for 44 hours. Pour the reaction mixture onto a mixture of 2N1-1CI and ice and stir well. Separate the cough substance by filtration, wash thoroughly with water, dry and crystallize from ethyl acetate. Yield: After crystallization from ethyl acetate, the desired 2-phenoxy-3-pyridylsulfonamide 17.5f is obtained with a melting point of 176°-178°C.

Example 4 N-[2-allyloxy-3-pyridylsulfonyl)-N-(4+s-dimethoxy-1,3,5-
) Production of riazin-2-yl]urea a) N-allyloxy-5-hyricylsulfonylphenylcarbame-1.4.85F in 50 m/dioxane was dissolved in 2-amine-4,6 in 50 tae of anhydrous dioxane. -Simethoxy 1,3.5-triazine 2.0! 1 and 0.09 me of triethylamine at 60° C. over 15 minutes. The reaction mixture is stirred at 70°C for 1.5 hours, filtered while warm, and vacuum-dot-dash at 50°C. The oily residue is then triturated with ether and filtered to give 328 tons of the desired sulfonylurea, mp 152 DEG -154 DEG C.

The starting material J-mer 2-allyloxy 8-5-hyridylsulfonylphenyl carbamate of the following formula is prepared as follows: b) Dimethylformamide 307! A solution of 4.7 f of diphenyl carbamate in anhydrous dimethylformamide is added dropwise to a (55%) suspension of 087 v of sodium hydride in anhydrous dimethylformamide over a period of 5 minutes at a temperature of up to 20°C. -Medium, 2-allyloxy-3-
A solution of 428 t of pyridylsulfonamide is added dropwise to the above reaction mixture over a period of 20 minutes at a maximum temperature of 20° C. and the contents are stirred at this temperature for 1 hour. The reaction solution is σ
Ethyl acid 130-1 Ice water 130- and 2N HCl 19
2- Absorb into the mixture. The organic solvent phase is separated, washed four times with cold water, dried over sodium phosphate and evaporated to dryness. The residue is triturated with ether, filtered and dried to yield the desired phenyl carbamate with a melting point of 144°-146°C5. Get El.

The following ureas are prepared according to the above examples: ', ): i and 1 8 () The following starting material pyridylsulfonamides of the formula ■ are prepared according to Example 1: H2-QC, H40
CH,s Io2-1o3℃H2-QC)1. Q (Child CH, 5121-121, 5℃H2-OCH, C=CH
5145-47℃H2-OC(CH,)=CH2565
-66℃H2-OCR, -CH=C(CH,),
3H2-OCH, CH=CHCI(3s 225-
226CH2-0CHF, 5H2-OCH4CF, 5H5-OCRF
, 2 H2-OC, 114C15 H2-OCF, CF, sH2-t)C,
)i,QC,l-1,5H2-QC,)1. OCH,C
1(=CH,5H2-OCH(CH,)OCH to C,3
b-CH,2-Qc2H,0CHss 6-CH,2-OCH,CH=CH,5b-CH,2
-OCR,C=CM56-CI(3
2-OCHF, 3b-CHa2
-QC,H,C15 b-CH34-QC,H,OCH,5 6-CH,4-OCH2CH=CF(,26-CH5a
-OCH,C=CH5 6-Cru 4-QC,f(,C13H2-SCH,
CH=CH,s H2-0CF, CFfF', 5H2
-8Cf廛゛,5 H2-8CH,(,:CH5 H2-SO,CtH,0CH3s H2-8O,CM,CH=Ct(,5 H2-802CH,C=CH5 H2-corner 5 175-176
CH2-NHCH56171-172C H2-N (C pigeon CH=CH,) 5 90
-91℃H2-Piperidi 5 155
-156℃H2-morpholino 5 18
! l-184CH2-(4'-benzylpiperazino)
3 164-165CH2-(4'-methylpiperazino) s 1so-1s4℃H
2-N(CHs)CACN sH2-N
(CtHa) CtH4CN sH2-p
henoxy 5 176-1
78CH2-QC, H40CH55 H2-OCH, CHICu2 3 144-
146CH2-ocu, c (CHs) = CL
3H2-OCH, CH=CHCH, 3 H2-8-C for CH=CH, 5 H2-0-CHeCH=C(CHa)t 36-
CHs 2-O-CHt= CH,5H2-OC
H2(,:CHs HN (CH3)t sHNtH, CH=CH, 39B -99'-17 Example 5: Example formulation for a compound of formula I (%
- weight percentage) a) Irrigation agent a) b) c
Compound represented by formula 1 20% 60% 0.5
% Sodium lignosulfonate 5% 5%
5% Sodium lauryl sulfate 6% --Sodium diisobutylna-7talenesulfonate -6% 6% Highly dispersed silicon #
5% 27% 27% power ori
7 67% -- Sodium Chloride -- 595% -- 595% Effectively mixed thoroughly and the mixture is milled well in a suitable mill, an irrigation agent is obtained which can be diluted with water to form any desired Concentrated suspensions can also be obtained.

b) Emulsion Concentrate a) b) Formula I
Compound represented by 10% 1%18 Octerphenol polyethylene (# ethylene 4 to 5 moles) 3%
3% calcium dotecylbenzenesulfonate
5%, 3% cyclohexanone 30%
10% xylene mixture 50% 79% An emulsion of any desired concentration can be prepared from this concentrate by diluting with water.

C) Powder a)
b) Compound C represented by formula 1
L1% 1% Talc 999% - Kaolin -99% A powder which can be taken directly is obtained by mixing the active ingredient with the carrier and milling the mixture in a suitable mill.

d) Extruded granules a),) Compound of formula I 10% 1% Sodium lignosulfone 2% 2% 11 (j.

Carboxymethylcellulose 1%
1% Kaolin 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.

e) Compound represented by a114 granule formula ■ 3% polyethylene glycol (molecular weight 200) 2% kaolin 94% The finely ground active ingredient is applied uniformly to the kaolin in a mixer and moistened with polyethylene glycol. become In this way, non-dusty granules are obtained.

f) Suspension concentrates a) b)
) Compound represented by formula 1 40% 5%
Ethylene glycol 10% 10% lignos,
Sodium sulfonate 10% 5%2
0 Ka'boxymethylcellulose/(1%,.

57% formaldehyde aqueous solution
. 2%. , 2% 75% silicone oil in the form of an aqueous emulsion 0.8% [18%
Water 32%
When the 77% finely ground active ingredient is homogeneously mixed with the auxiliaries, a suspension concentrate is obtained, from which a suspension concentrate of any desired concentration can be prepared by diluting with water.

g) Salt solution Compound of formula I 5% inglobilamine 1% water
91% biological test Example 6: Pre-emergence herbicidal action A plastic pot was filled with swollen barbaculite (concentration: 0A55f/Homare, water absorption amount: α5654/l).

21 After saturating the non-adsorbent vermiculite with an aqueous emulsion in deionized water containing the test compound at a concentration of 70.8 ppm, seeds of the following 'M@' were sown on the surface: Nasturtium officinalis
umofficinalia), Agrostis tenuis, Stellaria
Stellaria media and Digitalia sanguinalis
sanguinalis).

The pots were then kept in a climate-controlled room at 20° C., approximately 20 lux of radiation and 70% relative humidity.

During the 4-5 day germination phase, the pots were covered with light-transparent material and watered with deionized water to increase local humidity. After 5 days, use a commercially available liquid fertilizer (Green Jit).
reenzit (■)) was added to the water. The test was evaluated 12 days after sowing, and the effect on the plants was evaluated according to the following grades.

1: Plants do not germinate or all survive 2-5: Very strong effect 4-6: Average effect 22 7-8: Weak effect 9 No two effects, same as untreated control) Pre-emergence effect: Test compound emulsion Table 3 Example 7: Selectivity test in pre-emergence application Seeds of dicotyledonous and monocotyledonous weeds and cultivated plants were grown in a greenhouse with a diameter of 11 cm.
Sow in a pot. Immediately treat the soil surface with a diluted aqueous dispersion of the test compound. The concentration of active ingredient used is α25
0, 0.125 and 0.06 kg/ha. The pots were then placed in a greenhouse at 22'' to 25° C. and a relative humidity of 5° to 70%. The results of this test were evaluated after 3 weeks and the effectiveness was rated using the same rating as in Example 6.

Test results (before germination) %-4 1ry.

Example 8: Post-emergence herbicidal action (contact action) Many monocotyledonous and dicotyledonous weeds and cultivated plants were
At the leaf stage, an aqueous dispersion of the test compound was sprayed at an application rate of α5 kg active ingredient/ha, followed by 2 aa to 26 aa.
℃ and 45-60% relative humidity. The test was evaluated 15 days after treatment according to the same grades used in the pre-emergence test.

Post-emergence action diversion ratio: 26 active ingredients of α5 per hectare Example 9: Tropical intercropping growth suppression test plants [centrosema plumjeri and centrosema plumjeri]
pubescens)] was grown to full growth, and then pinched to a height of 60 cm. Seven days later the plants were sprayed with an aqueous emulsion of the test compound. The test plants were exposed to 70 °C relative humidity and 6000 °C for 14 hours per day.
The specimens were left at a daytime temperature of 27°C and a nighttime temperature of 21°C under an artificial lux lamp. The test was evaluated by observing and weighing new growth compared to control plants 4 weeks after application and determining plant growth inhibition.

In this test, plants treated with the compound of formula I were observed to have significantly reduced new growth (20% less than the new growth of untreated control plants) without damage.

Example 10: Growth control of soybean Soybean seeds are sown in a soil/peat/sand mixture (6:5:1) in a plastic container.The container is placed in an air-conditioned room and After about 6 weeks, by proper control of temperature, light, fertilizer addition and irrigation, the plants will develop to the 5-6 mitsuba leaf stage.The plants are then sprayed with an aqueous mixture of the compound represented by 2I until thoroughly wetted. The application rate of the active ingredient corresponds to 100 v/ha. The test results are evaluated approximately 5 weeks after application. Compared to the untreated control, the compound of formula I The number and weight of fruits increased significantly.

Example 11: Grain Growth Suppression Summer barley (Hordeum vulgare) and summer rye (5ecale) were sown in a greenhouse on sterilized soil in plastic beakers and watered as required. Ceremony of young branches of 7 grains about 21 days after sowing! The treatment was carried out by spraying an aqueous mixture of the compound represented by: The concentration is 1002 active ingredients per hectare.
It is. Grain growth evaluation was performed 10 and 21 days after application. Compared to the untreated control, the plant growth of the grains treated with the formula was significantly reduced compared to the control 60-12.
90%), and in some cases the stem diameter increased.

Example 15: Weed growth suppression Lolium perenne,
Poa pratensis, cow 7
Tuca ovina (Fe5tuca ovina), Camogaya (1
) actyl isglomerata ) and Cynodondoctylon weed seeds in a soil/peat/sand mixture (ratio 6:3) in a greenhouse.
:1) in a plastic blood vessel filled with water and sprinkled with water as necessary. The germinated weeds were cut weekly to a height of 4 cm above the soil and sprayed with an aqueous spray mixture of the compound of formula (2) approximately 50 days after sowing and 1 day after the last cut. The concentration of the test compound was 10 per hectare.
Corresponds to the application rate of 02. Weed growth was evaluated 21 days after application. The compound of formula (1) was effective in reducing new growth by 10 to 50 inches compared to the untreated control.

Patent applicant CiverGeigy Akchengesellschaft agent Patent attorney Yumi Sae (and 1 other person) 30 (C07D 401/12 213100 251100) 7132-
4C (C07D 401/14 11100 13100 239100 ) 13100 251100 ) Priority claim 04/28/1983 ■Switzerland (CH)
■2283783-8 0 Inventor Karl Glass 4312 Blumenrein 49 Magden, Switzerland 4 0 Inventor Willi Meyer 49 Thalweg 4125 Liechen, Switzerland

Claims (1)

[Scope of Claims] (1) The following formula ■: (wherein A is an alkynyl group having 5 to 6 carbon atoms, 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, C1-4 haloalkoxy group, C1-4 haloalkylthio group,
a C1-C6 alkyl group substituted by a C1-C4 haloalkylsulfinyl group or a C1-C4 haloalkylsulfonyl group;
or unsubstituted or C2-C6 alkenyl group substituted with the same substituents as C1-C6 alkyl group, or unsubstituted or)-rogen atom, cyano group, nitro group, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms,
-X-C1-C4-alkyl group, C1-C4 alkoxycarbonyl group, amino group, mono-(C1-C4 alkyl)amino group, carbamoyl group, mono- -t+ represents a phenyl group substituted with a di(alkyl having 1 to 4 carbon atoms) carbamoyl group, a sulfamoyl group, a heptano or a di(alkyl having 1 to 4 carbon atoms) sulfamoyl group, or A -X- forms an amino group -NR,R, 1E represents a methine group or a nitrogen atom, bird represents a hydrogen atom, /.rogen atom, an alkyl group having 1 to 4 carbon atoms, and 1 to 4 carbon atoms. an alkoxy group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, a haloalkoxy group having 1 to 4 carbon atoms, an alkoxyalkoxy group having 2 to 5 carbon atoms,
C1-C5 alkylthio group, C1-C5 alkylthio group
-5 alkylsulfinyl group or 1 carbon atom
represents an alkylsulfonyl group having 1 to 5 carbon atoms, and ``bird'' represents an alkyl group having 1 to 3 carbon atoms or an alkoxy group having 1 to 5 carbon atoms, which is unsubstituted or substituted with 1 to 5 710 atoms; is a hydrogen atom, a halogen atom, an amino group -N R4R5
or an alkyl group of 1 to 3 carbon atoms, which is unsubstituted or substituted with 1 to 3 halogen atoms; Number of carbon atoms: 1
represents an alkoxy group having 1 to 4 carbon atoms, R4 represents a hydrogen atom or a methyl group, R5 represents a hydrogen atom, an alkyl group having 1 to 2 carbon atoms, or a methoxy group, R and H each independently represent a hydrogen atom, Alkyl group having 1 to 4 carbon atoms, alkenyl group having 3 to 6 carbon atoms, alkynyl group having 5 to 76 carbon atoms, alkoxyalkyl group having 3 to 4 carbon atoms, alkoxyalkyl group having 3 to 4 carbon atoms, represents a cyanoalkyl group, or together with the silicon atom to which both are bonded, a saturated 5- or 6-membered ring member which can also contain an oxygen atom, a sulfur atom or -NB. also form a heterocycle, where avian represents a hydrogen atom, a C1-C4 alkyl group or a benzyl group, and X represents an oxygen atom, a sulfur atom, or a sulfinyl group or a sulfonyl bridge, with the proviso that - X-A represents an alkenyl sulfide group having 3 to 4 carbon atoms, an alkenyl sulfinyl group having 3 to 4 carbon atoms, or an alkenyl sulfonyl group having 3 to 4 carbon atoms; methoxymethyl, trifluoromethyl, nitro, cyano or methoxymethyl, the substituent - is a C1-C2 alkyl group, a C1-C2 alkoxy group or a methoxymethyl group. N-pyridylsulfonyl-N'-pyrimidinyl urea or N-pyridylsulfonyl-N'-triazinyl urea or a salt thereof, characterized in that it is represented by: (2) In formula ■, R Wataru represents a hydrogen atom and % A
TETR2, 几3 and X are formulas! A compound according to claim 1 having the same meaning as defined in . (3) The compound according to claim 1, wherein in formula (■), R1 represents a hydrogen atom, X represents an oxygen atom or a sulfur atom, and % Ay EH bird and bird represent the same meanings as defined in formula I.゛. (4) A compound according to claim 1, which is represented by the following formula: (wherein A, E, R, , R, and X have the same meanings as defined in Formula I). (5) The compound according to claim 1, which is represented by the following formula: (wherein A, E, R, and D have the same meanings as defined in Formula I). (6) The following formula: (In the formula, s A-Rt -& and bird represent the same meaning as defined in Formula I.) (7) The following formula: (In the formula, A, R1, Horse, and Rs are the formula The N-pyridylsulfonyl-N-)riazinyl urea according to claim 1, which is defined by 1 and has the same meaning as 9. (8) The following formula: (wherein A' represents an alkenyl group having 5 to 4 carbon atoms or an alkynyl group having 3 to 4 carbon atoms, and E, R, and avian are defined in the formula ) The compound according to claim 1, which has the same meaning as . <9) Claim 1, which is represented by the following formula: (In the formula, human represents an alkenyl group having 5 to 4 carbon atoms, or an alkoxyalkyl group having 3 to 4 carbon atoms.) N-pyridylsulfonyl-N'-4-methoxy-6-methyltriazin-2-ylurea. 2) The biridyl sulfonamide represented by the following formula ■: (wherein, A, R1, and X represent the same meanings as defined in formula It has the same meaning as defined in formula I, and Ph represents a phenyl group or a phenyl group substituted (by a halogen atom or an alkyl group). ) The following formula I, where ** indicates the reaction with the N-1 riazinyl car/<mate represented by Alkoxy group having 1 to 4 carbon atoms, alkylthio group having 1 to 4 carbon atoms, alkylsulfinyl group having 1 to 4 carbon atoms, alkylsulfonyl group having 1 to 4 carbon atoms, haloalkoxy group having 1 to 4 carbon atoms , a haloalkylthio group having 1 to 4 carbon atoms,
a C1-C6 alkyl group substituted by a C1-C4 haloalkylsulfinyl group or a C1-C4 haloalkylsulfonyl group;
or unsubstituted or C2-C6 alkenyl group substituted with the same substituents as C1-C6 alkyl group, or unsubstituted or halogen atom, cyano group, nitro group, carbon atom number 1-4 alkyl group, C1-4 haloalkyl group, -X
-C1-C4-alkyl group, C1-C4alkylsulfonyl group, amino group, mono- or di-(C1-C4alkyl)amino group,
Carbamoyl group, mono- or di(C1-C4alkyl)carbamoyl group, sulfamoyl group,
Mono- or di (alkyl having 1 to 4 carbon atoms)
represents a phenyl group substituted by a sulfamoyl group, or AX- forms an amino group -NR@R, E represents a methine group or a nitrogen atom, R represents a hydrogen atom, a halogen atom, a carbon atom, Alkyl group having 1 to 4 atoms, alkoxy group having 1 to 4 carbon atoms, haloalkyl group having 1 to 4 carbon atoms, haloalkoxy group having 1 to 4 carbon atoms, alkoxyalkoxy group having 2 to 5 carbon atoms , represents an alkylthio group having 1 to 5 carbon atoms, an alkylfinyl group having 1 to 5 carbon atoms or an alkylsulfonyl group having 1 to 5 carbon atoms, and R2 is unsubstituted or 1 to 3 halogen atoms. C 1 -C 3 alkyl group substituted by or C 1 -C 3 alkyl group substituted by
represents an alkoxy group, Rs is a hydrogen atom, a halogen atom, an amino group -NR, RB
t or unsubstituted or a C1 to C5 alkyl group substituted by 1 to 3 halogen atoms, or unsubstituted or substituted by a methoxy group, ethoxy group or 1 to 3 halogen atoms; Number of carbon atoms: 1
It represents an alkoxy group having 1 to 4 carbon atoms, R4 represents a hydrogen atom or a methyl group, and R6 represents a hydrogen atom, an alkyl group having 1 to 2 carbon atoms, or a methoxy group. Bird and crow each independently represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkenyl group having 3 to 6 carbon atoms, an alkynyl group having 3 to 6 carbon atoms, and a 3 to 6 carbon atom alkyl group.
represents an alkoxyalkyl group having 1 to 6 carbon atoms, a cyanoalkyl group having 1 to 4 carbon atoms, or together with the nitrogen atom to which both are bonded, an oxygen atom, a sulfur atom or a -N- group as a ring member also form a saturated 5- or 6-membered heterocycle which can also contain a hydrogen atom, a C1-C4 alkyl group or a benzyl group, and X is an oxygen atom, represents a sulfur atom, a sulfinyl group or a sulfonyl bridge, provided that -X-A is an alkenyl sulfide group having 3 to 4 carbon atoms, an alkenyl sulfinyl group having 3 to 4 carbon atoms, or 9 is an alkenyl having 3 to 4 carbon atoms; represents a sulfonyl group, and at the same time a hydrogen atom,...
When it represents a chlorogen atom, a methyl group, a methoxy group, a trifluoromethyl group, a nitro group, a cyano group or a methoxymethyl group, the substituent is an alkyl group having 1 to 2 carbon atoms, an alkyl group having 1 to 2 carbon atoms, alkoxy or methoxymethyl groups, and birds are limited to methyl or methoxy groups. ) A method for producing N-pyridylsulfonyl-N/-pyrimidinyl urea or N-pyridylsulfonyl-N'-tovazinylurea. 6υ The following formula PI: (In the formula, A, R, !, and X represent the same meanings as defined in the formula x and R3 have the same meanings as defined in formula (2). 6 alkynyl group, halogen atom, alkoxy group having 1 to 4 carbon atoms, alkylthio group having 1 to 4 carbon atoms, alkylsulfinyl group having 1 to 4 carbon atoms, alkylsulfonyl group having 1 to 4 carbon atoms, a haloalkoxy group having 1 to 4 carbon atoms, a haloalkylthio group having 1 to 4 carbon atoms,
a C1 to C4 haloalkylsulfinyl group, a C1 to C4 alkyl group substituted with a C1 to C4 haloalkylsulfinyl group, or an unsubstituted or C1 to C6 alkyl group; C2 -C6 alkenyl substituted with similar substituents or unsubstituted or halogen, cyanide, nitro, C1 -C4 alkyl, C1 -C4 haloalkyl group, -
X-C1-C4-alkyl group, C1-C4-alkyl group, C1-C4-alkyl group
to 4 alkoxycarbonyl group, amino group, heptano or di(alkyl having 1 to 4 carbon atoms) amino group, carbamoyl group, mono- or di([[1 to 4 alkyl having 10 to 40 carbon atoms)]carbamoyl group, sulfamoyl group , represents a phenyl group polysubstituted by a mono- or di(C1 -C4 alkyl)sulfamoyl group, or A-X- forms an amino group -N-R1 and E is a methine group; or represents a nitrogen atom, R1 is a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, or a haloalkyl group having 1 to 4 carbon atoms; 4 haloalkoxy group, alkoxyalkoxy group having 2 to 5 carbon atoms,
C1-C5 alkylthio group, C1-C5 alkylthio group
-5 alkylsulfinyl group or 1 carbon atom
represents an alkyl sulfonyl group having 1 to 5 carbon atoms, and the turtle represents an unsubstituted or polysubstituted alkyl group having 1 to 3 carbon atoms or 1 to 5 halogen atoms;
represents an alkoxy group of 5 to 5, R3 is a hydrogen atom, a halogen atom, an amino group -NR4R5
or an unsubstituted 'i or a C1-C3 alkyl group polysubstituted with 1-3 halogen atoms;
or unsubstituted or methoxy group, ethoxy group or 1
A tortoise represents a hydrogen atom or a methyl group, and a bird represents a hydrogen atom, an alkyl group having 1 to 2 carbon atoms or methoxy group; bird and horse each independently represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkenyl group having 3 to 6 carbon atoms, an alkynyl group having 3 to 6 carbon atoms, and 3 carbon atoms;
represents an alkoxyalkyl group having 1 to 6 carbon atoms, a cyanoalkyl group having 1 to 4 carbon atoms, or together with the nitrogen atom to which both are bonded, an oxygen atom, a sulfur atom or -NB as a ring member. - represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or a benzyl group, and X represents an oxygen atom. an atom, a sulfur atom, a sulfinyl group or a sulfonyl bridge, provided that -X-A is an alkenyl sulfide group having 5 to 4 carbon atoms, an alkenyl sulfinyl group having 3 to 4 carbon atoms, or an alkenyl sulfinyl group having 3 to 4 carbon atoms; It represents an alkenylsulfonyl group, and R and R are simultaneously a hydrogen atom and a halogen atom. If it represents a methyl group, methoxy group, trifluoromethyl group, nitro group, cyano group or methoxymethyl group,
Substituents are limited to C1-C2 alkyl groups, C1-C2 alkoxy groups or methoxymethyl groups, and R3 is limited to methyl or methoxy groups. ) A method for producing N-pyridylsulfonyl-N/-pyrimidinyl urea or N-pyridylsulfonyl-N'-triazinyl urea. 0り The following formula ■: (in the formula, %Rq is a phenyl group, a phenyl group substituted with a halogen atom, or an alkyl group having 1 to 4 carbon atoms, or an alkyl group having 1 to 4 carbon atoms, or 2 to 8 carbon atoms) represents an alkoxyalkyl group, Y represents a sulfur atom or an oxygen atom, and A,
R1 and X are formulas! It has the same meaning as defined in . ) is reacted with an amine represented by the following formula V:几3 (wherein A is an alkynyl group having 3 to 4 carbon atoms, a halogen atom, an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms) sulfinyl group, alkylsulfonyl group having 1 to 4 carbon atoms, haloalkoxy group having 1 to 4 carbon atoms, haloalkylthio group having 1 to 4 carbon atoms,
a C1-C4 haloalkylsulfinyl group or a C1-C6 alkyl group substituted by a C1-C4 haloalkylsulfonyl group;
or unsubstituted or C2-C6 alkenyl group substituted with the same substituents as C1-C6 alkyl group, or unsubstituted or)-logen atom, cyano group, nitro group, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms,
-X-C1 -C4-alkyl, C1 -C4alkoxycarbonyl, amino, mono- or di-(C1 -C4alkyl))amino, carbamoyl, mono- but represents a phenyl group substituted with a di(alkyl having 1 to 4 carbon atoms) carbamoyl group, a sulfamoyl group; A group -NR.R1 is formed, E represents a methine group or a nitrogen atom, and R1 is a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a carbon atom a haloalkyl group having 1 to 4 carbon atoms, a haloalkoxy group having 1 to 4 carbon atoms, an alkoxyalkoxy group having 2 to 5 carbon atoms,
C1-C5 alkylthio group, C1-C5 alkylthio group
9 to 5 alkylsulfinyl group has 1 carbon atom
9 represents an alkyl group having 1 to 5 carbon atoms, and 9 represents an alkyl group having 1 to 5 carbon atoms, and 9 represents an alkyl group having 1 to 5 carbon atoms; , R3 is a hydrogen atom, a hydrogen atom, an amino group -NR4R
, or an alkyl group having 1 to 3 carbon atoms, which is unsubstituted or substituted with 1 to 3 halogen atoms,
or unsubstituted or methoxy group, ethoxy group or 1
i represents an alkoxy group having 1 to 4 carbon atoms substituted with 3 halogen atoms, R4 represents a hydrogen atom or a methyl group, and ``a'' represents a hydrogen atom or an alkyl group having 1 to 2 carbon atoms; or represents a methoxy group, and Ra and R7 are each independently a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkenyl group having 3 to 6 carbon atoms, an alkynyl group having 3 to 6 carbon atoms, or a carbon atom number Represents an alkoxyalkyl group having 3 to 6 carbon atoms, a cyanoalkyl group having 1 to 4 carbon atoms, or together with the nitrogen atom to which both are bonded, an oxygen atom, a sulfur atom or -NR as a ring member. also form saturated 5- or 6-membered heterocycles which can also contain groups, avian being a hydrogen atom, a C1-C4 alkyl group or a benzyl group, and 1X being an oxygen atom, A sulfur atom or a sulfinyl group represents a sulfonyl bridge, provided that -X-A is an alkenyl sulfide group having 3 to 4 carbon atoms, an alkenyl sulfinyl group having 3 to 4 carbon atoms, or an alkenyl group having 3 to 4 carbon atoms. If R represents a sulfonyl group and R simultaneously represents a hydrogen atom, a methyl group, a methoxy group, a trifluoromethyl group, a nitro group, a cyano group or a methoxymethyl group, then the substituent EL! is limited to C 1 -C 2 alkyl, C 1 -C 2 alkoxy or methoxymethyl, and avian is limited to methyl or methoxy. ) A method for producing N-pyridylsulfonyl-NF-pyrimidinyl urea or N-pyridylsulfonyl-N'-)riazinyl urea. a) The following formula ■: (wherein A is an alkynyl group having 3 to 6 carbon atoms, a halogen atom, an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, or an alkylthio group having 1 to 4 carbon atoms; 4 alkylsulfinyl group, C1 to C4 alkylsulfonyl group, C1 to C4 haloalkoxy group, C1 to C4 haloalkylthio group,
A haloalkylsulfinyl group having 1 to 4 carbon atoms, ti carbon a<1 to 4 haloalkylsulfonyl groups having 1 to 6 carbon atoms, or an unsubstituted or unsubstituted alkyl group having 1 to 4 carbon atoms; an alkenyl group having 2 to 6 carbon atoms substituted with the same substituent as the alkyl group in 6, or unsubstituted, rogene atom, cyano group, nitro group, 1 to 4 carbon atoms;
C1-C4-alkyl group, C1-C4-haloalkyl group, -X-C1-C4-alkyl group, C1-C4 alkoxycarbonyl group, amino group, mono- or di-(C1-C4) to 4 alkyl) amine group, carbamoyl group, mono- or di(alkyl having 1 to 4 carbon atoms) carbamoyl group, sulfamoyl group, mo/-4* is di(alkyl having 1 to 4 carbon atoms) sulfamoyl group represents a phenyl group substituted by, or AX- forms an amino group -NR,R. R1 is a hydrogen atom, a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, a haloalkoxy group having 1 to 4 carbon atoms; , 2 to 5 carbon atoms
represents an alkoxyalkoxy group, an alkylthio group having 1 to 5 carbon atoms, an alkylsulfinyl group having 1 to 5 carbon atoms, or an alkylsulfonyl group having 1 to 5 carbon atoms, and X is an oxygen atom, a sulfur atom, or a sulfinyl group. represents a group or a sulfonyl bridge. ) Pyridyl sulfonamide. 1 Formula ■: (wherein A is an alkynyl group having 3 to 6 carbon atoms, a halogen atom, an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, or an alkylthio group having 1 to 4 carbon atoms) an alkylsulfinyl group having 1 to 4 carbon atoms, an alkylsulfonyl group having 1 to 4 carbon atoms, a haloalkoxy group having 1 to 4 carbon atoms, a haloalkylthio group having 1 to 4 carbon atoms,
a C1-C6 alkyl group substituted by a C1-C4 haloalkylsulfinyl group or a C1-C4 haloalkylsulfonyl group;
or unsubstituted or C2-C6 alkenyl group substituted with the same substituents as C1-C6 alkyl group, or unsubstituted or halogen atom, cyano group, nitro group, carbon atom number 1 to 4 alkyl group, C1 to 4 haloalkyl group, -X
-C1 -C4alkyl, C1 -C4alkoxycarbonyl, amino, mono- or di-(C1 -C4alkyl))amino, carbamoyl, mono- or di(C1 -C4alkyl), A carbamoyl group (alkyl having 1 to 4 carbon atoms), a sulfamoyl group, a monomer represents a phenyl group substituted by a di(alkyl having 1 to 4 carbon atoms) sulfamoyl group, or AX- is an amino group -NR6R , and R1 is a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, or a haloalkyl group having 1 to 4 carbon atoms. represents a haloalkoxy group, an alkoxyalkoxy group having 2 to 5 carbon atoms, an alkylthio group having 1 to 5 carbon atoms, an alkylsulfinyl group having 1 to 5 carbon atoms, or an alkylsulfonyl group having 1 to 5 carbon atoms; , X represents an oxygen atom, a sulfur atom, a sulfinyl group, or a sulfonyl bridge. ) Pyridylsulfonyl isocyanate or Hiroisothiocyanate. 0!19 Next 2■: (wherein R is a phenyl group or a phenyl group substituted with a halogen atom or an alkyl group having 1 to 4 carbon atoms,
or an alkoxy group having 1 to 4 carbon atoms or an alkoxyalkoxy group having 2 to 8 carbon atoms;
Y represents an oxygen atom or a sulfur atom, and A represents an alkynyl group having 3 to 6 carbon atoms, a halogen atom, an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, or an alkylthio group having 1 to 4 carbon atoms. 4 alkylsulfinyl group, C1 to C4 alkylsulfonyl group, C1 to C4 haloalkoxy group, C1 to C4 haloalkylthio group, C1 to C4 haloalkylsulfinyl group, or a C1-C6 alkyl group substituted by a C1-C4 haloalkylsulfonyl group, or an unsubstituted C1-C6 alkyl group;
L< is a C2-C6 alkenyl group substituted with the same substituent as a C1-C6 alkyl group, or unsubstituted, or a halogen atom, a cyano group,
Nitro group, C1-C4 alkyl group, C1-C4 haloalkyl group, -X-C1-C4 alkyl group, -X-C1-C4 haloalkyl group
-4-alkyl group, C1 -C4 alkoxycarbonyl group, amino group, mono- or di-(C1 -C4 alkyl)amine group, carbamoyl group, mono- or di-(C1 -C4 alkyl) group, 4 alkyl)carbamoyl group, sulfamoyl group, monomer represents a phenyl group substituted by a di(alkyl having 1 to 4 carbon atoms) sulfamoyl group, or AX- is an amino group -NR,,R, and R is a hydrogen atom, a halogen atom, a C1-C4 alkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkyl group, a C1-C4 alkyl group, or a C1-C4 alkyl group. represents a haloalkoxy group, an alkoxyalkoxy group having 2 to 5 carbon atoms, an alkylthio group having 1 to 5 carbon atoms, an alkylsulfinyl group having 1 to 5 carbon atoms, or an alkylsulfonyl group having 1 to 5 carbon atoms; A pyridylsulfonyl carbamate represented by (X represents an oxygen atom, a sulfur atom, a sulfinyl group or a sulfonyl bridge). (IQ The sulfonylurea represented by the formula ■ is an amine,
A method for producing an addition salt of a compound according to any one of claims 10 to 12, which comprises reacting with an alkali metal hydroxide, an alkaline earth metal hydroxide, or a quaternary ammonium base. (17) The following formula I: (wherein A is an alkynyl group having 5 to 6 carbon atoms, a halogen atom, an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, or 1 carbon atom) an alkylsulfinyl group having 1 to 4 carbon atoms, an alkylsulfonyl group having 1 to 4 carbon atoms, a haloalkoxy group having 1 to 4 carbon atoms, a haloalkylthio group having 1 to 4 carbon atoms,
a C1-C6 alkyl group substituted by a C1-C4 haloalkylsulfinyl group or a C1-C4 haloalkylsulfonyl group;
or unsubstituted or C2-C6 alkenyl group substituted with the same substituents as C1-C6 alkyl group, or unsubstituted or halogen atom, cyano group, nitro group, carbon atom number 1-4 alkyl group, C1-4 haloalkyl group, -X
-C1 -C4alkyl, C1 -C4alkoxycarbonyl, amino, mono- or di-(C1 -C4alkyl))amino, carbamoyl, mono- or di(C1 -C4alkyl), represents a phenyl group substituted by a C1-C4 alkyl) carbamoyl group, a sulfamoyl group, a mono- or di-(C1-C4 alkyl)sulfamoyl group, or A-X- is an amino group- NR, R, are formed, E represents a methine group or a nitrogen atom, and R1 is a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, and 1 carbon atom. a haloalkyl group having 1 to 4 carbon atoms, a haloalkoxy group having 1 to 4 carbon atoms, an alkoxyalkoxy group having 2 to 5 carbon atoms,
C1-C5 alkylthio group, C1-C5 alkylthio group
-5 alkylsulfinyl group or 1 carbon atom
represents an alkyl group having 1 to 5 carbon atoms; avian represents an alkyl group having 1 to 5 carbon atoms, which is unsubstituted or substituted with 1 to 3 atoms; and ``bird'' represents an alkoxy group having 1 to 3 carbon atoms; , Bird is a hydrogen atom, a hydrogen atom, an amino group -NR4几6
or unsubstituted or carbon alkyl group having 1 to 3 carbon atoms substituted with 1 to 5 halogen atoms, or unsubstituted or carbon substituted with methoxy group, ethoxy group or 1 to 5 halogen atoms Number of atoms: 1
represents an alkoxy group having 1 to 4 carbon atoms; 几4 represents a hydrogen atom or a methyl group; 电 represents a hydrogen atom, an alkyl group having 1 to 2 carbon atoms, or a methoxy group; C1-C4 alkyl group, C3-C6 alkenyl group, C3-C6 alkynyl group, C3-C6 alkoxyalkyl group, C1-C4 cyanoalkyl group a saturated 5- or 6-membered heterocycle which, together with the nitrogen atom to which both are attached, can also contain as ring members an oxygen atom, a sulfur atom or a -NR11 group; and R8 represents a hydrogen atom, a C1-C4 alkyl group or a benzyl group, and X represents an oxygen atom, a sulfur atom, a sulfinyl group or a sulfonyl bridge, provided that -XA is represents a C3 -C4 alkenylsulfide group, a C3 -C4 alkenylsulfinyl group or a C3 -C4 alkenylsulfonyl group, and the bird simultaneously represents a hydrogen atom, /
・When representing a rogene atom, methyl group, methoxy group, trifluoromethyl group, nitro group, cyan group or methoxymethyl group, the substituent R is an alkyl group having 1 to 2 carbon atoms, or an alkyl group having 1 to 2 carbon atoms. is limited to an alkoxy group or a methoxymethyl group, and R3 is limited to a methyl group or a methoxy group. ) Weeding and plant growth characterized by containing at least one type of N-pyridylsulfonyl-N'-pyrimidinylurea or N-pyridylsulfonyl-N'-triazinylurea represented by the following along with a carrier and/or other auxiliary agents. Regulatory composition. αυ N-pyridylsulfonyl N/- represented by the formula ■
Pyrimidinyl urea or N-pyridinylsulfonyl-N
18. A composition according to claim 17 for controlling undesirable plant growth, comprising a triazinyl urea or a composition containing said compound. al N-pyridylsulfonyl N/- represented by formula ■
Pyrimidinyl urea or N-pyridylsulfonyl-N'
- The composition according to claim 17 for inhibiting plant growth, comprising a composition containing triazinyl urea or the compound. N-pyridylsulfonyl N/-pyrimidinyl urea or N-pyridylsulfonyl-N'- represented by the formula ■
19. The composition according to claim 18, comprising a composition containing triazinyl urea or the compound, for selectively controlling weeds in a field where useful plants are planted before or after germination. Qυ N-pyridylsulfonyl N/- represented by the formula ■
Pyrimidinyl urea or N-pyridylsulfonyl-N'
- triazinyl urea or the like compound according to claim 19, for inhibiting the growth of plants after the two-leaf stage by pre-emergence application. (2) The composition according to claim 20, wherein the useful plants are sugar cane, cereals, corn, rice, soybeans, and cotton. (2) N-pyridylsulfonyl-N' represented by formula ■
-pyrimidinyl urea or N-pyridylsulfonyl-N
20. A composition according to claim 19 for regulating the growth of cultivated plants to obtain an increase in yield, comprising: /-triazinyl urea or a composition containing said compound. ■ Claim 23 in which the useful plant crop is soybean
Compositions as described in Section. (C) Claim 1 in which the plant is an intercropped leguminous plant
Composition according to item 9.