JP3010709B2 - Sulfamide sulfonylurea derivatives and herbicides - Google Patents

Description

Description: TECHNICAL FIELD The present invention relates to novel sulfamidosulfonylurea derivatives and herbicides containing them as an active ingredient.

[Conventional technology and issues]

It is essential to use herbicides to protect important crops such as rice, wheat, corn, soybeans, cotton and beet from weed damage and increase the yield. Particularly in recent years, a selective herbicide capable of selectively killing only weeds without showing phytotoxicity to the crops even when the crops and weeds are simultaneously treated on the cultivated land where these useful crops and weeds coexist is desired. ing.
Further, from the viewpoints of prevention of environmental pollution, reduction of economic cost in transportation and application, etc., research for compounds having a low dose and a high herbicidal effect has been continued for many years. Although some of the compounds having such properties are currently used as selective herbicides, there is still a need for better new compounds with these properties.

As a prior art having a structure similar to the compound of the present invention, a compound in which a sulfonylurea is bonded to a nitrogen atom is disclosed in
-103371, JP-A-60-48973 and JP-A-1
-151577.

JP-A-60-48973 and JP-A-1-151577 disclose compounds in which a sulfonylurea is bonded to a nitrogen atom of a sulfonamide structure. However, as in the compound of the present invention, a nitrogen atom of a special sulfamide structure is disclosed. Is a novel compound that has never been known before.

[Means for solving the problem]

The present inventors have studied for many years to develop a herbicide that is selective for important crops, and in order to produce a compound having higher herbicidal activity and selectivity, the herbicidal properties of many compounds have been studied. Have been considered. As a result, the general formula (I): R ¹¹ represents an alkyl group having 1 to 6 carbon atoms, 3 carbon atoms.
Cycloalkyl group having 3 to 7 carbon atoms, cycloalkenyl group having 3 to 7 carbon atoms, alkyl group having 1 to 6 carbon atoms substituted by cycloalkyl group having 3 to 7 carbon atoms, C1-C6 alkyl, C2-C6 alkenyl, C2-C2 substituted by mono- or polyhalogenocycloalkyl groups
An alkynyl group having 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms substituted by an alkoxy group having 1 to 6 carbon atoms, and an alkyl group having 1 to 6 carbon atoms substituted by an alkylthio group having 1 to 6 carbon atoms. An alkyl group, an alkyl group having 1 to 6 carbon atoms substituted by a mono- or dialkylamino group having 1 to 6 carbon atoms, a mono- or polyhalogenoalkyl group having 1 to 6 carbon atoms, 2 carbon atoms A mono- or polyhalogenoalkenyl group having 1 to 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms substituted by a cyano group, and 1 to 6 carbon atoms substituted by an alkoxycarbonyl group having 1 to 6 carbon atoms. Alkyl group, having 1 to 1 carbon atoms
An alkenyl group having 2 to 6 carbon atoms substituted by an alkoxycarbonyl group having 6 carbon atoms, and an alkenyl group having 1 carbon atom substituted by an alkoxycarbonyl group having 1 to 6 carbon atoms.
A mono- or polyhalogenoalkyl group having 1 to 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms substituted by a mono- or dialkylaminocarbonyl group having 1 to 6 carbon atoms,
C 1 -C 6 alkoxycarbonyl group, C 1 -C 6 mono- or dialkylaminocarbonyl group, cyano group, C 1 -C 6 alkylcarbonyl group substituted by C 1 -C 6 An alkyl group having 1 to 6 carbon atoms, a mono- or polyhalogenoalkylcarbonyl group having 1 to 6 carbon atoms, a phenyl group and a benzyl group (provided that these phenyl groups and benzyl groups are halogen atoms May be mono- or poly-substituted by a trifluoromethyl group, a nitro group, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or an alkoxycarbonyl group having 1 to 6 carbon atoms. .) 3- to 6-membered heterocycle (provided that these heterocycles contain a heteroatom selected from a nitrogen atom, an oxygen atom and a sulfur atom) These hetero rings include a halogen atom, a trifluoromethyl group, a nitro group, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, and 1 carbon atom. 6 to 6 may be mono- or poly-substituted.) 3- to 6-membered heterocyclic ring (provided that these heterocyclic rings are a heteroatom selected from a nitrogen atom, an oxygen atom or a sulfur atom) The hetero ring includes a halogen atom, a trifluoromethyl group, a nitro group, an alkyl group having 1 to 6 carbon atoms, and 1 hetero atom.
It may be mono- or poly-substituted by an alkoxy group having 1 to 6 carbon atoms or an alkoxycarbonyl group having 1 to 6 carbon atoms. ) Represents an alkyl group having 1 to 6 carbon atoms, and R ¹² represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms,
An alkenyl group having 2 to 6 carbon atoms, an alkynyl group having 2 to 6 carbon atoms, a phenyl group and a benzyl group (provided that these phenyl groups and benzyl groups are a halogen atom, a trifluoromethyl group, R ¹³ is an alkyl group having 1 to 6 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms, which may be substituted with an alkoxycarbonyl group having 1 to 6 carbon atoms. Phenyl group and benzyl group (provided that these phenyl group and benzyl group are a halogen atom, a trifluoromethyl group, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, alkoxycarbonyl group, may be substituted by a nitro group.) represents, or, R ¹² and R ¹³ are 5 to 7 membered saturated with the nitrogen atom to which they are attached A heterocyclic, or, R
¹² and R ¹³ represent a 5- to 7-membered heterocyclic ring saturated with the oxygen atom and the nitrogen atom to which they are bonded, R ²¹ is an alkyl group having 1 to 6 carbon atoms, 3 carbon atoms
C7-C7 cycloalkyl group, C1-C6 alkyl group substituted by C3-C7 cycloalkyl group, C3-C7 mono- or polyhalogenocycloalkyl group substituted by C3-C7 cycloalkyl group 1 to 1 carbon atoms
6 alkyl groups, alkenyl groups having 2 to 6 carbon atoms, alkynyl groups having 2 to 6 carbon atoms, alkyl groups having 1 to 6 carbon atoms substituted by alkoxy groups having 1 to 6 carbon atoms, carbon An alkyl group having 1 to 6 carbon atoms substituted by an alkylthio group having 1 to 6 atoms, an alkyl group having 1 to 6 carbon atoms substituted by a mono- or dialkylamino group having 1 to 6 carbon atoms A mono- or polyhalogenoalkyl group having 1 to 6 carbon atoms, a mono- or polyhalogenoalkenyl group having 2 to 6 carbon atoms,
A C1-C6 alkyl group substituted by a cyano group, a C1-C6 alkyl group substituted by a C1-C6 alkoxycarbonyl group, a C1-C6 alkoxy An alkenyl group having 2 to 6 carbon atoms substituted by a carbonyl group, an alkyl group having 1 to 6 carbon atoms substituted by a mono- or dialkylaminocarbonyl group having 1 to 6 carbon atoms, 1 carbon atom 6 to 6 alkoxycarbonyl groups, mono- or dialkylaminocarbonyl groups having 1 to 6 carbon atoms,
A cyano group, an alkyl group having 1 to 6 carbon atoms substituted by an alkylcarbonyl group having 1 to 6 carbon atoms, an alkylcarbonyl group having 1 to 6 carbon atoms, 1 carbon atom
To 6 mono- or polyhalogenoalkylcarbonyl groups, phenyl groups and benzyl groups (provided that these phenyl groups and benzyl groups are a halogen atom, a trifluoromethyl group, a nitro group, an alkyl group having 1 to 6 carbon atoms, A mono- or poly-substituted alkoxy group having 1 to 6 carbon atoms or an alkoxycarbonyl group having 1 to 6 carbon atoms, or a 5- to 6-membered heterocyclic ring (provided that these heterocyclic rings are a nitrogen atom , A heteroatom selected from an oxygen atom or a sulfur atom in the ring, which contains 1 to 3 heteroatoms, a halogen atom, a trifluoromethyl group,
It may be mono- or poly-substituted by a nitro group, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or an alkoxycarbonyl group having 1 to 6 carbon atoms. R ²² represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, R ²³ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, R ²⁴ represents a hydrogen atom or a carbon atom An alkyl group having 1 to 6 atoms,
A halogen atom, a mono- or polyhalogenoalkyl group having 1 to 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms substituted by an alkoxy group having 1 to 6 carbon atoms, alkenyl having 2 to 6 carbon atoms An alkyl group having 1 to 6 carbon atoms substituted with an oxy group, 2 to 6 carbon atoms
An alkyl group having 1 to 6 carbon atoms substituted by an alkynyloxy group, an alkyl group having 1 to 6 carbon atoms substituted by a mono- or polyhalogenoalkoxy group having 1 to 6 carbon atoms, carbon atom An alkyl group having 1 to 6 carbon atoms substituted by an alkylthio group having 1 to 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms substituted by an alkylsulfonyl group having 1 to 6 carbon atoms, and a cyano group A substituted alkyl group having 1 to 6 carbon atoms, an alkoxycarbonyl group having 1 to 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms substituted by an alkoxycarbonyl group having 1 to 6 carbon atoms, 1 carbon atom
6 alkylcarbonyl groups, 1 to 6 carbon atoms substituted by an alkylcarbonyl group having 1 to 6 carbon atoms.
R ²⁵ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms; R ²⁶ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms; R ²⁷ represents a hydrogen atom Represents an alkyl group having 1 to 6 carbon atoms, R ²⁸ represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms,
A mono- or polyhalogenoalkyl group having 1 to 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms substituted by an alkoxy group having 1 to 6 carbon atoms, 2 to 6 carbon atoms
An alkyl group having 1 to 6 carbon atoms, substituted by an alkenyloxy group, an alkyl group having 1 to 6 carbon atoms, substituted by an alkynyloxy group having 2 to 6 carbon atoms, 1 to 6 carbon atoms An alkyl group having 1 to 6 carbon atoms, which is substituted by an alkylthio group of
Alkyl groups having 1 to 6 carbon atoms, substituted by alkylsulfonyl groups having 1 to 6 carbon atoms, alkyl groups having 1 to 6 carbon atoms, substituted by cyano groups, 1 to 6 carbon atoms
An alkoxycarbonyl group, an alkylcarbonyl group having 1 to 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms substituted by an alkoxycarbonyl group having 1 to 6 carbon atoms, an alkylcarbonyl having 1 to 6 carbon atoms L represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, or an alkyl group having 2 to 6 carbon atoms, X represents an alkynyl group, X represents an oxygen atom or a sulfur atom, A represents a CH group or a nitrogen atom; B and C each independently represent an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a mono- or poly- It represents a halogenoalkyl group, a mono- or polyhalogenoalkoxy group having 1 to 4 carbon atoms, a halogen atom, or a monoalkylamino group having 1 to 4 carbon atoms. The sulfamide sulfonylurea derivative represented by the formula (I) and the agriculturally suitable salts thereof (hereinafter, referred to as the compound of the present invention) are significantly different from many weeds in both soil treatment and foliage treatment. The present invention was found to have high herbicidal activity and high safety against important crops such as wheat, corn, cotton, soybean, beet and rice. On the other hand, the compound of the present invention exhibits a high herbicidal activity at a very low dose in comparison with conventional herbicides, and is therefore useful as a herbicide for orchards and non-agricultural lands.

The compound of the present invention represented by the general formula (I) can be easily produced by selecting any one of the following reaction formulas 1 to 6.

Reaction formula 1 [Wherein, Q, G, L and X have the same meaning as described above. That is, the sulfamidosulfonyliso (thio) cyanate derivative (II) is dissolved in a sufficiently dried inert solvent such as dioxane, acetonitrile, and acetone, and the pyrimidine or triazine derivative represented by the formula (III) is added thereto. By adding and stirring, the compound generally reacts promptly to obtain the compound (I) of the present invention. When the reaction is difficult to proceed, the reaction can be easily promoted by adding a small amount of a suitable base, for example, triethylamine, triethylenediamine, pyridine, sodium methoxide, sodium hydride, potassium carbonate and the like.

Reaction formula 2 [Wherein, Q, G, L and X have the same meaning as described above. Y represents an alkyl group having 1 to 6 carbon atoms or a phenyl group. That is, sulfamide sulfonamide derivative (IV)
Is reacted with chloroformic acid (thio) ester or carbonic acid (thio) ester in a solvent such as acetone, methyl ethyl ketone or acetonitrile in the presence of a base such as potassium carbonate to obtain compound (V). Next, the compound (I) of the present invention can be obtained by heating the compound (III) in a solvent such as toluene.

Reaction formula 3 [In the formula, Q, G, L and Y have the same meaning as described above. The reaction of the sulfamides (VI) with phenyl N-chlorosulfonylcarbamate (VII; Y = phenyl group) or alkyl N-chlorosulfonylcarbamate (VII; Y = lower alkyl group) is performed in 1 mole of the sulfamides (VI). In contrast, the reaction is carried out using the carbamate derivative (VII) in an amount of 0.5 to 3.0 mol. Preferably, the range of 0.9 to 1.2 mol is appropriate.

The reaction temperature can be arbitrarily selected from the range of -50 ° C to 100 ° C, but is preferably in the range of -20 ° C to 30 ° C.

This reaction is carried out using various bases. The base is used in an amount of 0.5 to 4.0 mol per 1 mol of the sulfamides (VI).

Suitable bases include, for example, metal hydrides such as sodium hydride, metal alkoxides such as sodium ethoxide, alkyl metals such as n-butyl lithium, triethylamine, pyridine, 1,8-diazabicyclo [5,4,
0] -7-undecene (DBU) and the like; and inorganic bases such as potassium hydroxide and sodium hydroxide.

 Particularly preferably, metal hydrides are used.

Suitable solvents for this reaction include solvents inert to this reaction, for example, benzene, toluene, xylene-based aromatic hydrocarbons, dichloromethane, chloroform, halogenated hydrocarbons such as carbon tetrachloride, ethyl ether, isopropyl ether, Ethers such as dioxane and tetrahydrofuran; nitriles such as acetonitrile and propionitrile; hydrocarbons such as petroleum ether, petroleum benzene and hexane; ketones such as acetone and methyl ethyl ketone; esters such as ethyl acetate; dimethylformamide and dimethylacetamide And amides such as hexamethylphosphoric triamide.

 These solvents may be used alone or as a mixture.

Particularly preferably, ethers or amides are used.

Then, phenyl N-sulfamidesulfonylcarbamate (V; X = O, Y = phenyl group) or alkyl
N-sulfamide sulfonyl carbamate (V; X = O, Y =
By heating the lower alkyl group) and the compound (III) in a solvent such as benzene or toluene, the compound of the present invention (I;
X = O).

Reaction formula 4 [Wherein, Q, G, L and Y have the same meaning as described above. That is, sulfamide sulfonamide derivative (IV)
Is reacted with a carbamate derivative (VIII) in a solvent such as acetone, acetonitrile or dioxane in the presence of an inorganic base such as potassium carbonate or an organic base such as triethylamine or DBU to obtain the compound of the present invention (I; X =
O) can be obtained.

Reaction formula 5 [Wherein, Q, G and L have the same meaning as described above. That is, the amines (III) are reacted with chlorosulfonyl isocyanate in a solvent such as tetrahydrofuran, dimethoxyethane, acetonitrile, propionitrile, dimethylformamide, dichloromethane, dichloroethane, benzene, or toluene, and subsequently triethylamine, pyridine, The compound of the present invention (I; X = O) is reacted with a sulfamide (VI) in the presence of a base such as sodium hydride, sodium methoxide, sodium ethoxide, sodium hydroxide, calcium hydroxide, and potassium carbonate. Obtainable.

Reaction formula 6 [Wherein, Q and G have the same meanings as described above. That is, sulfamide sulfonamide derivative (IV)
Is reacted with an isothiocyanate derivative (IX) in a solvent such as acetone, acetonitrile or dioxane in the presence of an inorganic base such as potassium carbonate or an organic base such as triethylamine or DBU to obtain the compound of the present invention (I;
X = S, L = H).

The raw material sulfamidosulfonyliso (thio) cyanate derivative (II) used in Reaction Scheme 1 can be obtained from the sulfamidosulfonamide derivative (IV) by JP-A-58-148879 and JP-A-59-31775. The compound can be synthesized with reference to the methods described in Japanese Patent Application Laid-Open No. 55-13266 and Japanese Patent Application Laid-Open No. 55-13266.

In addition, sulfamide sulfonyl isocyanate (II; X
= 0) can also be synthesized by the method of Reaction Scheme 7 with reference to the method described in JP-A-49-81320 and the like.

Reaction formula 7 [Wherein, Q has the same meaning as described above. Intermediate sulfamide sulfonyl iso (thio) cyanate derivative (II), sulfamide sulfonamide derivative (IV), phenyl N-sulfamide sulfonyl (thio) carbamate (V; Y = phenyl) used in the present invention Groups) and alkyl N-sulfamidosulfonyl (thio) carbamates (V; Y = lower alkyl groups) are also novel compounds. Sulfamide sulfonamide derivatives (I
V) can be synthesized from the sulfamide derivative (VI) using the methods of Reaction Schemes 8 and 9 below.

Reaction formula 8 [Wherein, Q has the same meaning as described above. In the reaction formula 8, the tert-butyl group is removed using trifluoroacetic acid.

The amount of trifluoroacetic acid can be arbitrarily selected from equimolar to excess. There is no problem even if trifluoroacetic acid is used as a solvent.

The reaction temperature can be arbitrarily selected from the range of -50 ° C to 80 ° C. Preferably, the range is from -20 ° C to 30 ° C.

When a solvent is used in this reaction, a solvent inert to the reaction, for example, benzene, toluene, xylene-based aromatic hydrocarbon, dichloromethane, chloroform, halogenated hydrocarbon such as carbon tetrachloride, ethyl ether, isopropyl Ethers, dioxane, ethers such as tetrahydrofuran, acetonitrile, nitriles such as propionitrile, petroleum ether, petroleum benzyl, hydrocarbons such as hexane, acetone, ketones such as methyl ethyl ketone, esters such as ethyl acetate, dimethylformamide, Amides such as dimethylacetamide and hexamethylphosphoric triamide. These solvents may be used alone or as a mixture.

Reaction formula 9 (In the formula, Q has the same meaning as described above.) In Reaction Scheme 9, the reaction between t-butanol and chlorosulfonyl isocyanate is carried out by a method known per se, for example, with reference to JP-A-50-101323. Can be implemented.

The reaction of the sulfamides (VI) with tert-butylsulfamoyl chloride is carried out using 0.5 to 3.0 moles of tert-butylsulfamoyl chloride per mole of the sulfamides (VI). Preferably, the range of 0.9 to 1.2 mol is appropriate.

The reaction temperature can be arbitrarily selected from the range of -50 ° C to 100 ° C, but is preferably in the range of -20 ° C to 30 ° C.

This reaction is carried out using various bases. The amount of the base is 0.5 to 4.0 mol per 1 mol of the sulfamides (VI). Preferably, a range of 0.8 to 2.2 molar amount is appropriate. Suitable bases include, for example, metal hydrides such as sodium hydride, metal alkoxides such as sodium ethoxide, alkyl metals such as n-butyl lithium,
Organic bases such as triethylamine, pyridine, 1,8-diazabicyclo [5,4,0] -7-undecene (DBU) and inorganic bases such as potassium hydroxide and sodium hydroxide are used.

 Particularly preferably, metal hydrides are used.

Suitable solvents for this reaction include solvents inert to this reaction, for example, benzene, toluene, xylene-based aromatic hydrocarbons, dichloromethane, chloroform, halogenated hydrocarbons such as carbon tetrachloride, ethyl ether, isopropyl ether, Ethers such as dioxane and tetrahydrofuran; nitriles such as acetonitrile and propionitrile; hydrocarbons such as petroleum ether, petroleum benzene and hexane; ketones such as acetone and methyl ethyl ketone; esters such as ethyl acetate; dimethylformamide and dimethylacetamide And amides such as hexamethylphosphoric triamide.

 These solvents may be used alone or as a mixture.

Particularly preferably, ethers or amides are used.

In Reaction Scheme 3, phenyl N-chlorosulfonyl carbamate (VII; Y = phenyl group) and alkyl N
-Chlorsulfonyl carbamate (VII; Y = lower alkyl group) can be prepared by a method known per se, for example, Chemische
It can be synthesized with reference to Bemiste (Chemische Berichte), vol. 96, p. 56 (1963).

Sulfamides (VI) used as starting materials for the above reaction are described in Journal of American Chemical
Society (Journal of the American Chemical Soc
Society, 66, 1242 pages (1944), US Patent 2,
826,594, Journal of Synthetic Organic Chemistry, Vol. 27 (No. 10), 980
Page (1969), US Patent 2,624,729, Chemische Berichte, 111, 191
5 pages (1978), JP-A-53-79894, JP-A-58
-208289, Indian Journal of Chemis, Section B (Indian Journal of Chemis
try, Section B), vol. 21B, p. 941 (1982), and the like.

Representative examples are N, N-dimethyl-N'-methoxysulfamide, N-methyl-N-methoxy-N'-ethylsulfamide, N-methyl-N-methoxy-N'-methoxysulfamide, N , N-dimethyl-N'-trifluoromethylthiosulfamide, N-methyl-N-methoxy-
The methods for synthesizing N'-trichloromethylthiosulfamide and 2-methoxy-1,2,5-thiazoazolidine-1,1-dioxide are described in Reaction Schemes 10 to 15.

Reaction formula 10 Reaction formula 11 Reaction formula 12 Reaction formula 13 Reaction formula 14 Reaction formula 15 Hereinafter, synthesis examples of the compound of the present invention will be specifically described with reference to examples, but the present invention is not limited thereto.

Example 1 1-[(N-dimethylsulfamoyl-N-methoxy-
Synthesis of amino) sulfonyl] -3- (4,6-dimethoxypyrimidin-2-yl) urea Anhydrous T containing 1.87 g (42.9 mmol) of 55% sodium hydride
In 100 ml of HF, N, N-dimethyl- dissolved in 20 ml of anhydrous THF
3.0 g (19.5 mmol) of N'-methoxysulfamide was added under ice-cooling, followed by stirring at the same temperature for 10 minutes.

Next, phenyl N-chlorosulfonyl carbamate
50 ml of an anhydrous THF solution containing 4.83 g (20.5 mmol) was added dropwise, and the temperature was gradually raised to room temperature, followed by stirring at room temperature for 1 hour.

The reaction mixture was poured into 500 ml of ice water containing 5 g of 35% hydrochloric acid, and extracted with diethyl ether. The diethyl ether layer was washed sequentially with water and saturated saline, then dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. 5.4 g of phenyl N-[(N-dimethylsulfamoyl-N-methoxy-amino) sulfonyl] carbamate was obtained as an orange oil.

Next, 3 g (8.5 mmol) of the above compound, 0.93 g (6 mmol) of 2-amino-4,6-dimethoxypyrimidine, 20 ml of anhydrous benzene
Was heated to reflux for 10 minutes. After allowing to cool, the solvent was distilled off under reduced pressure, and the residue was washed with ether and collected by filtration to obtain the desired 1-[(N-dimethylsulfamoyl-N-methoxy-amino) sulfonyl] -3- (4 1,6-Dimethoxypyrimidin-2-yl) urea (1.0 g) was obtained.

Melting point 166-167 ° C Example 2 1-[(N- (N-methyl-N-methoxyaminosulfonyl) -N-ethyl-amino) sulfonyl] -3- (4,
Synthesis of 6-dimethoxypyrimidin-2-yl) urea Anhydrous T containing 1.60 g (36.7 mmol) of 55% sodium hydride
To 50 ml of HF, 2.8 g (16.7 mmol) of N-methyl-N-methoxy-N'-ethylsulfamide dissolved in 20 ml of anhydrous THF was added under ice-cooling, followed by stirring at the same temperature for 10 minutes.

Next, phenyl N-chlorosulfonyl carbamate 4.
30 ml of anhydrous THF containing 13 g (17.5 mmol) was added dropwise, and the temperature was gradually raised to room temperature, followed by stirring at room temperature for 1 hour.

The reaction mixture was poured into 500 ml of ice water containing 4 g of 35% hydrochloric acid, and extracted with diethyl ether. The diethyl ether layer was washed sequentially with water and saturated saline, then dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. As an orange oil, phenyl N-[(N- (N-methyl-
N-methoxyaminosulfonyl) -N-ethyl-amino) sulfonyl] carbamate (5.0 g) was obtained.

Next, 2.5 g (6.8 mmol) of the above compound and 2-amino-4,6-
0.74 g (4.8 mmol) of dimethoxypyrimidine, anhydrous benzene
50 ml of the mixture was heated at reflux for 10 minutes. After cooling, the solvent was distilled off under reduced pressure, and the residue was washed with ether and collected by filtration.
The desired 1-[(N- (N-methyl-N-methoxyaminosulfonyl) -N-ethyl-amino) sulfonyl] -3
-(4,6-dimethoxypyrimidin-2-yl) urea 1.2 g
I got

Melting point 157-158 ° C Example 3 1- (2-methoxy-1,2,5-thiadiazolidine-1,1-)
Synthesis of Dioxide-5-sulfonyl-3- (4,6-dimethoxypyrimidin-2-yl) urea In 15 ml of anhydrous tetrahydrofuran (THF) containing 0.25 g (6.25 mmol) of 60% sodium hydride, 0.43 g (2.83 mmol) of 2-methoxy-1,2,5-thiadiazolidine-1,1-dioxide dissolved in 5 ml of anhydrous THF. ) Was added under ice-cooling, followed by stirring at room temperature for 14 hours under a nitrogen stream.

Next, after cooling the system to 0 ° C., an anhydrous THF solution containing 0.7 g (3 mmol) of phenyl N-chlorosulfonylcarbamate
10 ml was added dropwise, and then the temperature was gradually raised to room temperature, followed by stirring at room temperature for 1 hour.

Pour the reaction mixture into 100 ml of ice water containing 0.6 g of 35% hydrochloric acid,
Extracted with diethyl ether. The diethyl ether layer was washed sequentially with water and saturated saline, then dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. As a yellow viscous oil, the target phenyl N- (2-methoxy-1,
0.7 g of 2,5-thiadiazolidine-1,1-dioxide-5-sulfonyl) carbamate was obtained.

Next, 0.7 g (2 mmol) of the above compound, 0.31 g (2 mmol) of 2-amino-4,6-dimethoxypyrimidine, 10 ml of anhydrous benzene
Was heated to reflux for 10 minutes. After allowing to cool, the solvent was distilled off under reduced pressure, and the obtained residue was washed with diethyl ether to give the desired 1- (2-methoxy-1,2,5-thiadiazolidine-1,1-dioxide-5). -Sulfonyl) -3- (4,6
-Dimethoxypyrimidin-2-yl) urea 0.5 g was obtained.

Melting point: 162 to 163 ° C. Structural formulas and physical properties of compounds synthesized by using the same method as in the above Examples are shown below.

Next, examples of compounds included in the present invention, including the compounds synthesized in the above Examples, are shown in Tables 1 to 26 below, but the compounds of the present invention are not limited thereto.

 However, the symbols in the table have the following meanings.

Me; methyl group, Et; ethyl group, Pr-n; normal propyl group, Pr-i; isopropyl group, Pr-c; cyclopropyl group,
Bu-n; normal butyl group, Bu-s; secondary butyl group, Bu-i; isobutyl group, Bu-t; tertiary butyl group, Pen-n; normal pentyl group, Ph; phenyl group, Gn is It is synonymous with G and means the following Ga, Gb, Gc.

Ga = G1 to G13 (that is, any of G1 to G13).

Gb = G1 to G6 (that is, any of G1 to G6).

Gc = G1 to G3 (that is, any of G1 to G3).

In applying the compound of the present invention as a herbicide, generally a suitable carrier, for example, a solid carrier such as clay, talc, bentonite, diatomaceous earth or water, alcohol (methanol, ethanol, etc.), aromatic hydrocarbons (benzene, toluene, Xylene, etc.), chlorinated hydrocarbons, ethers, ketones, esters (ethyl acetate, etc.) and acid amides (dimethylformamide, etc.). A dispersant, a suspending agent, a penetrant, a spreading agent, a stabilizer, and the like are added, and the composition can be put to practical use in any form such as a liquid, an emulsion, a wettable powder, a powder, a granule, and a flowable.

Next, examples of blending of a herbicide containing the compound of the present invention as an active ingredient are shown, but the present invention is not limited thereto. In the following formulation examples, "parts" means parts by weight.

Formulation Example 1 wettable powder Compound of the present invention No. 1 20 parts Siegrite A 76 parts (kaolin-based clay: trade name of Siglite Co., Ltd.) Solpol 5039 2 parts (Nonionic surfactant) And anionic surfactant: Toho Kagaku Co., Ltd. Carplex (anti-caking agent) ... 2 parts (white carbon: Shionogi & Co., Ltd. trade name) To obtain a wettable powder.

Formulation Example 2 Water-dispersible compound of the present invention No.2 40 parts Siegrite A 54 parts (kaolin-based clay: trade name of Sigleite Industry Co., Ltd.) Solpol 5039 2 parts (Nonionic surfactant) Mixture of anionic and anionic surfactants: Toho Chemical Co., Ltd.) Carplex (anti-caking agent) 4 parts (white carbon: Shionogi & Co., Ltd.) To obtain a wettable powder.

Formulation Example 3 Emulsion Compound of the present invention No.3 5 parts Xylene 75 parts Dimethylformamide 15 parts Solpol 2680 5 parts (mixture of nonionic surfactant and anionic surfactant : Trade name of Toho Chemical Co., Ltd.) The above was uniformly mixed to prepare an emulsion. For use, the above emulsion was diluted 10 to 10,000 times and dispersed so that the amount of the active ingredient was 0.005 kg to 10 kg per hectare.

Formulation 4 Flowable Compound of the present invention No. 4 25 parts Agrisol S-710 10 parts (Nonionic surfactant: Kao Corporation) Lunox 1000C 0.5 part (Anionic surfactant: Toho Chemical Co., Ltd. 1% Rhodopol water 20 parts (thickener: Rhone Poulin Co., Ltd.) Water 44.5 parts The above were uniformly mixed to form a flowable agent.

Formulation Example 5 Flowable Compound of the present invention No. 20 ... 40 parts Agrizole S-710 ... 10 parts (Nonionic surfactant: trade name of Kao Corporation) Lunox 1000C ... 0.5 part (Anionic surfactant: Toho Chemical Co., Ltd. 1% Rhodopol water 20 parts (thickener: Rhone Poulin Co., Ltd.) Water 29.5 parts The above were uniformly mixed to form a flowable agent.

Formulation Example 6 Granules Compound of the present invention No. 22 1 part Bentonite 55 parts Talk 44 parts After uniformly mixing and pulverizing the above, a small amount of water was added, followed by stirring, mixing and kneading, followed by extrusion. Granulated by a granulator and dried to form granules.

In addition, the compound of the present invention may be mixed with other kinds of herbicides, various insecticides, fungicides, synergists and the like at the time of preparation or spraying as needed.

Examples of the above other herbicides include, for example, Farm Chemicals. Handbook (Farm Chemicals Handbook) 1
There are compounds described in the 989 edition.

For example, the compounds of the present invention include alachlor, acetochlor, metolachlor, primisulfuron, nicosulfuron, atrazine, cyanazine, EPTC, 2,4-D, butyrate, dicamba, bromoxynil, tridiphane,
Methosulfuron-methyl, thiphansulfuron-methyl, triasulfuron, isoprothiuron, chlorotoluron, diflufenican, metabenzthiazurone, diclohop-methyl, difenzoquat, fenoxaprop-ethyl, bentazone, trifluralin, fendimethalin and U.S. Patent No. 4,668,277 N-
[(4,6-Dimethoxypyrimidin-2-yl) aminocarbonyl] -3-chloro-4-methoxycarbonyl-1
Herbicides such as -methylpyrazole-5-sulfonamide, 1,8-naphthoic anhydride and N, N-diallyl-2,2
Mixing with herbicide safeners such as dichloroacetamide is possible.

In addition, the compound of the present invention can also be applied to the control of various weeds in non-agricultural lands such as athletic fields, vacant lots, track ends in addition to agricultural and horticultural fields such as fields, paddy fields, orchards, Although there are differences depending on the application time, application method, target grass species, cultivated crops, etc., it is generally appropriate that the amount of the active ingredient is about 0.005 to 10 kg per hectare.

Next, the usefulness of the compound of the present invention as a herbicide will be specifically described in the following test examples.

However, the compound numbers in the test examples correspond to the aforementioned numbers.

Test Example-1 Herbicidal Effect Test by Soil Treatment Put sterilized flooded soil in a plastic box 15 cm long, 22 cm wide and 6 cm deep, and add nobies, crabgrass, cyperaceae, inuhozuki, cornflower, oak, rice, corn, wheat, Soybean, cotton mixed, about 1.5cm
After covering the soil, the active ingredient was evenly sprayed on the soil surface so as to have a predetermined ratio. The chemical solution at the time of spraying was prepared by diluting a wettable powder appropriately adjusted in accordance with the above-mentioned formulation examples and the like with water and spraying the solution with a small spray. Four weeks after spraying the chemical solution, the herbicidal effect on crops and various weeds was examined according to the following criteria.

The results are shown in Table 27. (Compound No. corresponds to compound No. described in the Examples.) Some of the compounds of the present invention have selectivity for certain crops.

Judgment criteria 5: Herbicidal rate 90% or more (almost completely dead) 4: Herbicidal rate 70-90% 3: Herbicidal rate 40-70% 2: Herbicidal rate 20-40% 1: Herbicidal rate 5-20% 0: Herbicidal rate 5% or less (almost no efficacy) However, the above-mentioned herbicidal rate was obtained by measuring the above-ground fresh grass weight in the chemical-treated area and the above-ground fresh grass weight in the non-treated area by the following formula.

Test Example-2 Test of herbicidal effect by foliage treatment Put sterilized flood soil in a plastic box 15 cm long, 22 cm wide and 6 cm deep, and add nobies, crabgrass, cyperacea, inuhozuki, cornflower, oak, rice, corn, wheat, Soybean, cotton, and beet seeds were each sown in spots and covered with about 1.5 cm of soil. When the various plants reached the 2-3 leaf stage, they were evenly sprayed on the foliage so that the amount of the active ingredient became a predetermined ratio. The chemical solution at the time of spraying was prepared by diluting the wettable powder of the above-described formulation example with water, and spraying the spray solution over the entire foliage of various weeds with a small spray. Four weeks after spraying the chemical solution, the herbicidal effect on crops and various weeds was examined in accordance with the criteria in Test Example-1. The results are shown in Table 28. (Compound No. corresponds to compound No. described in Examples.) Next, the present inventors conducted a study to increase the herbicidal effect of the compound of the present invention. As a result, the compound of the present invention was compounded with any of alachlor, acetochlor, metolachlor, primisulfuron and nicosulfuron. Then
It has been found that each herbicidal effect can be obtained not only additively but also synergistically without damaging the crop.

The synergistic herbicidal effect of the herbicide mixture can be explained as follows. That is, each active compound often shows a disadvantage in its herbicidal activity. In this case, the herbicidal activity when the two active compounds are combined is a simple expression of the activity of each of the two compounds. If it is greater than the sum (expected activity), this is called synergy. The expected activity of a particular combination of two herbicides can be calculated as follows.

(Calculation of the synergistic and antagonistic response of a combination of Colby SR herbicides, see "Weed", Vol. 15, pp. 20-22, 1967) α: Inhibition rate when the herbicide A is treated at the amount of aKg / ha β: Inhibition rate when the herbicide B is treated at the amount of bKg / ha E: AKg / ha for the herbicide A and B for the herbicide B Inhibition rate expected when treated with an amount of bKg / ha That is, if the actual inhibition rate is greater than the above calculation, it can be said that the activity of the combination shows a synergistic effect.

Hereinafter, the present invention will be described in more detail with reference to Examples, but the compounds, dosage amounts, dosage forms, and the like in the present invention are not limited to Examples.

 In addition, "part" means all parts by weight.

Formulation Example 7 Water dispersant Compound of the present invention No. 3 10 parts Primisulfuron 10 parts Siegrite PFP 72 parts (Kaolin Clay: trade name of Sigleite Industry Co., Ltd.) Solpol 5039 2 parts ( Alkyl ether sulfate: trade name of Toho Chemical Industry Co., Ltd. Soybean oil: 2 parts Carplex # 80: 4 parts (white carbon: Shionogi & Co., Ltd. trade name) It was a sum.

Formulation Example 8 Water-dispersible compound of the present invention No. 3 10 parts Nicosulfuron 10 parts Siegrite PFP 72 parts (Kaolin Clay: trade name of Geekrite Industries, Ltd.) Solpol 5039 2 parts (alkyl Ether sulfate: trade name of Toho Chemical Industry Co., Ltd. Soybean oil: 2 parts Carplex # 80: 4 parts (white carbon: Shionogi & Co., Ltd. trade name) Agent.

Formulation Example 9 Suspension Compound of the present invention No. 3 2 parts Araclor 38 parts Sorbon T-80 5 parts (polyoxyethylene sorbitan monooleate: trade name of Toho Chemical Industry Co., Ltd.) Weegum 5 parts (Magnesium aluminum silicate: Vanderbil company name) Water ...... 50 parts or more are mixed uniformly and pulverized using a sand mill, etc.
A suspension having a particle size of 5 microns or less was obtained.

Formulation Example 10 Suspension Compound of the present invention No. 3 2 parts acetochlor 38 parts Sorbon T-80 5 parts (polyoxyethylene sorbitan monooleate: trade name of Toho Chemical Industry Co., Ltd.) Vegum 5 parts (Magnesium aluminum silicate: Vanderbil company name) Water ...... 50 parts or more are mixed uniformly and pulverized using a sand mill, etc.
A suspension having a particle size of 5 microns or less was obtained.

Formulation column 11 Granules Compound of the present invention No. 3 5 parts Metrachlor 75 parts Alon A 7 parts (polycarboxylate: trade name of Toa Gosei Chemical Co., Ltd.) Sun extract C 10 parts ( Lignin sulfonate: Sanyo Kokusaku Pulp Co., Ltd.) New Rex Powder: 2 parts (DBS-Na: Nippon Oil & Fats Co., Ltd.) Siegrite PFP: 1 copy (Kaolin Clay: Siglite Industrial Co., Ltd.) Name) An appropriate amount of water was added and mixed and pulverized to form a slurry, which was then granulated while removing water with a spray drier.

Formulation Example 12 Granules Compound of the present invention No. 3 5 parts Araclor 75 parts Alon A 7 parts (polycarboxylate: trade name of Toa Gosei Chemical Co., Ltd.) Sun extract C 10 parts ( Lignin sulfonate: Sanyo Kokusaku Pulp Co., Ltd.) New Rex Powder: 2 parts (DBS-Na: Nippon Oil & Fats Co., Ltd.) Siegrite PFP: 1 copy (Kaolin Clay: Siglite Industrial Co., Ltd.) Name) An appropriate amount of water was added and mixed and pulverized to form a slurry, which was then granulated while removing water with a spray drier.

Test Example-3 Herbicidal effect test by soil treatment Put sterilized field soil in a plastic box of 30 cm in length, 30 cm in width and 10 cm in depth, and sow corn, enokorogusa, ichibi, and fir seed in the form of spots, and 0.5 c
m Covered soil. The treatment was performed on the day of sowing with a spray water volume of 5 / a. The chemical solution at the time of spraying was appropriately adjusted according to the above-mentioned formulation example, diluted with water, and sprayed with a small spray. Above-ground fresh weight of each weed 3 weeks after spraying the chemical was measured, and the inhibition rate (%) was determined by the following equation.

Table 29 shows the results of the herbicidal effect test of the single agent.

 Table 30 shows the results of the herbicidal effect test of the mixture.

(Compound No. corresponds to compound No. described in the Examples.) Test Example-4 Test of Herbicidal Effect by Growing Treatment Place sterilized field soil in a plastic box 30 cm long, 30 cm wide and 10 cm deep, Seeds of corn, enokorogosa, ibis, and firgrass are each spotted and 0.5c
m Covered soil. On the 10th day of sowing, the growing season was sprayed with a spraying water amount of 5 / a. The chemical solution at the time of spraying was appropriately adjusted according to the above-mentioned formulation example, diluted with water, and sprayed with a small spray. Aboveground fresh weight of each weed was measured two weeks after spraying the chemical, and the inhibition rate (%) was determined in the same manner as in Test Example-3.

 Table 31 shows the results of the herbicidal effect test of the single agent.

 Table 32 shows the results of the herbicidal effect test of the mixture.

(Compound No. corresponds to compound No. described in Examples.)

────────────────────────────────────────────────── ─── Continued on front page (51) Int.Cl. ⁷ Identification code FI C07D 417/12 C07D 417/12 (31) Priority claim number Japanese Patent Application No. 2-89629 (32) Priority date April 4, 1990 Date (1990.4.4) (33) Priority claiming country Japan (JP) (31) Priority claim number Japanese Patent Application No. 2-96820 (32) Priority date April 12, 1990 (1990. (33) Priority claim country Japan (JP) (31) Priority claim number Japanese Patent Application No. 2-156439 (32) Priority date June 14, 1990 (1990. 6.14) (33) Priority claim Country Japan (JP) (72) Inventor Koichi Suzuki 1470 Shirooka, Shirooka-cho, Shiraoka-cho, Minami-Saitama-gun, Saitama Nissan Chemical Industry Co., Ltd. (72) Inventor Shigeomi Watanabe Shiraoka, Minamisaitama-gun, Saitama 1470 Ohira Shiraoka Examiner, Biological Science Laboratory, Nissan Chemical Industry Co., Ltd. Shunichi Yokoo (56) References JP-A-2-45473 (JP, A) JP-A-1-151577 (JP, A) JP-A-60-48973 (JP, A) (58) Fields investigated (Int. Cl. ⁷ , DB name) C07D 239/47 C07D 239/52 C07D 239/42 C07D 251/16 C07D 417/12 CA (STN) REGISTRY (STN)

Claims (3)

(57) [Claims] 1. A compound of the general formula (I): [Where Q is R ¹¹ represents an alkyl group having 1 to 6 carbon atoms, 3 to
7 cycloalkyl group, C3-7 cycloalkenyl group, C1-6 alkyl group substituted by C3-7 cycloalkyl group, C3-7 monoalkyl group -Alternatively, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, a carbon atom having 2 to 2 carbon atoms, which is substituted by a polyhalogenocycloalkyl group.
An alkynyl group having 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms substituted by an alkoxy group having 1 to 6 carbon atoms, and an alkyl group having 1 to 6 carbon atoms substituted by an alkylthio group having 1 to 6 carbon atoms. An alkyl group, an alkyl group having 1 to 6 carbon atoms substituted by a mono- or dialkylamino group having 1 to 6 carbon atoms, a mono- or polyhalogenoalkyl group having 1 to 6 carbon atoms, 2 carbon atoms A mono- or polyhalogenoalkenyl group having 1 to 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms substituted by a cyano group, and 1 to 6 carbon atoms substituted by an alkoxycarbonyl group having 1 to 6 carbon atoms. Alkyl group, having 1 to 1 carbon atoms
An alkenyl group having 2 to 6 carbon atoms substituted by an alkoxycarbonyl group having 6 carbon atoms, and an alkenyl group having 1 carbon atom substituted by an alkoxycarbonyl group having 1 to 6 carbon atoms.
A mono- or polyhalogenoalkyl group having 1 to 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms substituted by a mono- or dialkylaminocarbonyl group having 1 to 6 carbon atoms,
C 1 -C 6 alkoxycarbonyl group, C 1 -C 6 mono- or dialkylaminocarbonyl group, cyano group, C 1 -C 6 alkylcarbonyl group substituted by C 1 -C 6 An alkyl group, an alkylcarbonyl group having 1 to 6 carbon atoms, a mono- or polyhalogenoalkylcarbonyl group having 1 to 6 carbon atoms, a phenyl group and a benzyl group (provided that these phenyl groups and benzyl groups are a halogen atom, A trifluoromethyl group, a nitro group, an alkyl group having 1 to 6 carbon atoms,
It may be mono- or poly-substituted by an alkoxy group having 1 to 6 carbon atoms or an alkoxycarbonyl group having 1 to 6 carbon atoms. ) A 3- to 6-membered heterocycle (provided that these heterocycles contain 1 to 3 heteroatoms selected from a nitrogen atom, an oxygen atom or a sulfur atom in the ring.
These heterocycles may be mono- or halogenated by a halogen atom, a trifluoromethyl group, a nitro group, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or an alkoxycarbonyl group having 1 to 6 carbon atoms. It may be poly-substituted. ) 3- to 6-membered heterocycle (provided that these heterocycles contain 1 to 3 heteroatoms selected from a nitrogen atom, an oxygen atom or a sulfur atom in the ring. In addition, these heterocycles may be a halogen atom , Trifluoromethyl group, nitro group, alkyl group having 1 to 6 carbon atoms, 1 carbon atom
It may be mono- or poly-substituted by an alkoxy group having 1 to 6 carbon atoms or an alkoxycarbonyl group having 1 to 6 carbon atoms. ) Represents an alkyl group having 1 to 6 carbon atoms, R ¹² represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, 6 alkynyl groups, phenyl groups and benzyl groups (provided that these phenyl groups and benzyl groups are a halogen atom, a trifluoromethyl group, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, R ¹³ may be an alkyl group having 1 to 6 carbon atoms, a phenyl group and a benzyl group (provided that these phenyl group and benzyl group are A halogen atom, a trifluoromethyl group, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an alkoxycarbonyl group having 1 to 6 carbon atoms, and a nitro group. Or R ¹² and R ¹³ represent a 5- to 7-membered heterocyclic ring saturated with the nitrogen atom to which they are attached, or R ¹²
And R ¹³ represent a 5- to 7-membered heterocyclic ring saturated with an oxygen atom and a nitrogen atom to which they are bonded, R ²¹ represents an alkyl group having 1 to 6 carbon atoms,
7 cycloalkyl groups, C 1 -C 6 alkyl groups substituted by C 3 -C 7 cycloalkyl groups, substituted by C 3 -C 7 mono- or polyhalogenocycloalkyl groups 1 to 6 carbon atoms
An alkyl group having 2 to 6 carbon atoms, an alkynyl group having 2 to 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms substituted by an alkoxy group having 1 to 6 carbon atoms, An alkyl group having 1 to 6 carbon atoms substituted by an alkylthio group having 1 to 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms substituted by a mono- or dialkylamino group having 1 to 6 carbon atoms, 1 carbon atom
Mono- or polyhalogenoalkyl group having 1 to 6 carbon atoms, mono- or polyhalogenoalkenyl group having 2 to 6 carbon atoms, alkyl group having 1 to 6 carbon atoms substituted by cyano group, 1 to 6 carbon atoms An alkyl group having 1 to 6 carbon atoms substituted by an alkoxycarbonyl group, an alkenyl group having 2 to 6 carbon atoms substituted by an alkoxycarbonyl group having 1 to 6 carbon atoms, 1 carbon atom
An alkyl group having 1 to 6 carbon atoms, an alkoxycarbonyl group having 1 to 6 carbon atoms, and a carbon atom having 1 to 6 carbon atoms which are substituted by a mono- or dialkylaminocarbonyl group having 1 to 6 carbon atoms.
A mono- or dialkylaminocarbonyl group having 1 to 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms substituted by an alkylcarbonyl group having 1 to 6 carbon atoms, an alkylcarbonyl group having 1 to 6 carbon atoms, 1 carbon atom
6, mono- or polyhalogenoalkylcarbonyl groups,
Phenyl group and benzyl group (provided that these phenyl group and benzyl group are a halogen atom, a trifluoromethyl group, a nitro group, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, Mono- or poly-substituted by 1 to 6 alkoxycarbonyl groups), 5- to 6-membered heterocycle (provided that these heterocycles are a heteroatom selected from a nitrogen atom, an oxygen atom and a sulfur atom) And the heterocyclic ring includes a halogen atom, a trifluoromethyl group, a nitro group, an alkyl group having 1 to 6 carbon atoms,
It may be mono- or poly-substituted by an alkoxy group having 1 to 6 carbon atoms or an alkoxycarbonyl group having 1 to 6 carbon atoms. R ²² represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, R ²³ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, R ²⁴ represents a hydrogen atom or a carbon atom C1-C6 alkyl group, halogen atom, C1-C6 mono- or polyhalogenoalkyl group, C1-C6 alkyl group substituted by C1-C6 alkoxy group An alkyl group having 1 to 6 carbon atoms, which is substituted by an alkenyloxy group having 2 to 6 carbon atoms, 1 to 1 carbon atoms, which is substituted by an alkyloxy group having 2 to 6 carbon atoms.
C6 alkyl group, C1-6 alkyl group substituted with C1-6 mono- or polyhalogenoalkoxy group, C1-6 alkylalkyl group substituted with C1-6 alkylthio group An alkyl group having 1 to 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms substituted by an alkylsulfonyl group having 1 to 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms substituted by a cyano group,
An alkoxycarbonyl group having 1 to 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms substituted by an alkoxycarbonyl group having 1 to 6 carbon atoms, an alkylcarbonyl group having 1 to 6 carbon atoms, and a carbon atom Represents an alkyl group having 1 to 6 carbon atoms substituted by an alkylcarbonyl group having 1 to 6; R ²⁵ represents a hydrogen atom; an alkyl group having 1 to 6 carbon atoms; R ²⁶ represents a hydrogen atom; R ²⁷ represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, R ²⁸ represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a carbon atom A mono- or polyhalogenoalkyl group having 1 to 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms substituted by an alkoxy group having 1 to 6 carbon atoms, 2 to 6 carbon atoms
An alkyl group having 1 to 6 carbon atoms, substituted by an alkenyloxy group, an alkyl group having 1 to 6 carbon atoms, substituted by an alkynyloxy group having 2 to 6 carbon atoms, 1 to 6 carbon atoms An alkyl group having 1 to 6 carbon atoms, which is substituted by an alkylthio group of
Alkyl groups having 1 to 6 carbon atoms, substituted with alkylsulfonyl groups having 1 to 6 carbon atoms, alkyl groups having 1 to 6 carbon atoms substituted with cyano groups, 1 to 6 carbon atoms
An alkoxycarbonyl group, an alkylcarbonyl group having 1 to 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms substituted by an alkoxycarbonyl group having 1 to 6 carbon atoms, an alkylcarbonyl having 1 to 6 carbon atoms L represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkyl group having 2 to 6 carbon atoms, X represents an alkynyl group, X represents an oxygen atom or a sulfur atom, A represents a CH group or a nitrogen atom; B and C each independently represent an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a mono- or poly- It represents a halogenoalkyl group, a mono- or polyhalogenoalkoxy group having 1 to 4 carbon atoms, a halogen atom, or a monoalkylamino group having 1 to 4 carbon atoms. ] Or a salt thereof. [2] one of the compounds described in the above [1]
A selective herbicide comprising a seed or two or more kinds as an active ingredient. (3) a compound of the formula (1);
Species or two or more, and alachlor, acetochlor,
A herbicidal composition comprising one of metolachlor, primisulfuron and nicosulfuron as an active ingredient.