JPH08311062A - Pyridonesulfonylurea-based compound, its production and herbicide containing the same - Google Patents

Abstract

PURPOSE: To produce a new pyridonesulfonylurea-based compound, having excellent herbicidal effects and useful as a herbicide. CONSTITUTION: This pyridonesulfonylurea-based compound of formula I [Q is a group of formula II [R1 is H, an alkyl, an alkenyl, etc.; G is a halogen, an alkyl. an alkenyl, etc.; n is an integer of 0-3] or formula III; Rg is Hor an alkyl; X and Y are each independently a halogen, an alkyl, a haloalkyl, etc.; A is CH or N} or its salt, e.g. N-[(4,6-dimethoxypyrimidin-2-yl) aminocarbonyl]-[1-(n-propyl)-2(1H)-pyridone]-3-sulfonamide. The compound of formula I is obtained by reacting, e.g. a pyridone-based compound of the formula Q-SO2 NH2 with a compound of formula IV (R9 is an alkyl or an aryl) as starting raw materials in the presence of a base at -20 to +100 deg.C for 0.01-24hr. The pyridone-based compound is a new intermediate compound for the compound of formula I.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a novel pyridonesulfonylurea compound useful as an active ingredient of a herbicide.

[0002]

2. Description of the Related Art U.S. Pat. No. 4,435,206 discloses an alkyl group, a trifluoromethyl group, a pyridine ring,
Pyridine sulfonamide compounds in which an alkoxycarbonyl group or the like is substituted are described, and JP-A-63-
146873 describes pyridinesulfonamide compounds in which an aminocarbonyl group is substituted on the pyridine ring, but the pyridonesulfonylurea of the present invention is more effective than those compounds, that is, compounds having various substituents on the pyridine ring. The system compounds are completely different in chemical structure in that they are compounds having various substituents on the pyridone ring.

[0003]

DISCLOSURE OF THE INVENTION Problems to be Solved by the Invention
General formula (I);

[Chemical 43]

[0004]

[Chemical 44] And R ₁ is a hydrogen atom, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted alkoxy group, an optionally substituted alkylthio group, An optionally substituted alkylcarbonyl group, an optionally substituted alkoxycarbonyl group, an optionally substituted alkylsulfinyl group, an optionally substituted alkylsulfonyl group,

[0005]

Embedded image And G is a halogen atom, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted alkoxy group, an optionally substituted alkylthio group, a substituted Optionally substituted alkylcarbonyl group, optionally substituted alkoxycarbonyl group, optionally substituted alkylsulfinyl group, optionally substituted alkylsulfonyl group,

[0006]

Embedded image And R ₂ and R ₃ are each independently a hydrogen atom, an alkyl group, an alkylcarbonyl group, an alkylsulfinyl group or an alkylsulfonyl group, and R ₄ , R ₅ and R
₈ are each independently a hydrogen atom or an alkyl group, R ₆
And R ₇ are each independently a hydrogen atom, an alkyl group, an alkylcarbonyl group or an alkoxycarbonyl group, and n
Is an integer of 0 to 3, X and Y are each independently a halogen atom, an alkyl group, a haloalkyl group, an alkoxyalkyl group, an alkoxy group, a haloalkoxy group, a monoalkylamino group or a dialkylamino group, and A is CH or N), a pyridonesulfonylurea compound or a salt thereof, a method for producing the same, a herbicide containing them, a method for controlling harmful weeds using them, and an intermediate compound for producing the same Regarding

In the above general formula (I), an alkyl group which may be substituted, an alkenyl group which may be substituted, an alkynyl group which may be substituted, an alkoxy group which may be substituted, which is contained in R ₁ and G, As the substituent of the optionally substituted alkylthio group, the optionally substituted alkylcarbonyl group and the optionally substituted alkoxycarbonyl group,
Halogen atom, alkyl group, alkoxy group, alkylthio group, alkylcarbonyl group, alkoxycarbonyl group, alkylsulfinyl group, alkylsulfonyl group,
Optionally substituted phenyl group, optionally substituted benzyloxy group, monoalkylamino group, dialkylamino group, -CN group-NO ₂ group and the like, optionally substituted alkylsulfinyl group and substituted Examples of the substituent of the alkylsulfonyl group that may be mentioned include a halogen atom, an alkyl group, an alkoxy group, an optionally substituted phenyl group, and an optionally substituted benzyloxy group. Further, as the substituent of the phenyl group which may be substituted and the benzyloxy group which may be substituted as the above-mentioned substituent, a halogen atom, an alkyl group, an alkoxy group, an alkylthio group, an alkylcarbonyl group, an alkoxycarbonyl group, Alkylsulfinyl group, alkylsulfonyl group, phenyl group, benzyloxy group, monoalkylamino group, dialkylamino group, -CN group, -NO
₂ groups and the like. The number of substitutions of these substituents is 1
Alternatively, it may be two or more, and in the case of two or more, the substituents may be the same or different.

In the general formula (I), R ₁ , G, R ₂ and R
₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₈ and the alkyl group and the alkyl moiety contained in X and Y, and the alkyl group and the alkyl moiety as the substituent contained in R ₁ and G have carbon atoms. Is 1 to 6, preferably 1 to 4 and is linear or branched, for example, methyl group, ethyl group, propyl group,
Examples thereof include an isopropyl group, a butyl group, a tertiary butyl group, a pentyl group, and a hexyl group. The alkenyl group and alkynyl group contained in R ₁ and G have 2 to 6 carbon atoms, preferably 2 to 4 carbon atoms. Examples thereof include linear or branched ones such as vinyl group, allyl group, butadienyl group, isopropenyl group, ethynyl group and propynyl group. Examples of the halogen atom contained in G, X and Y and the halogen atom as a substituent contained in R ₁ , G, X and Y include each atom of fluorine, chlorine, bromine or iodine. The number of substitution of the halogen atom may be 1 or 2 or more, and when it is 2 or more, they may be the same or different.

In the pyridonesulfonylurea compounds represented by the above general formula (I) or salts thereof, R ₁ is a hydrogen atom, an optionally substituted alkyl group, an optionally substituted alkenyl group or an optionally substituted alkynyl. Group, optionally substituted alkoxy group, optionally substituted alkoxycarbonyl group, optionally substituted alkylsulfonyl group or

[0010]

[Chemical 47] A group, G is a halogen atom, an optionally substituted alkyl group, an optionally substituted alkoxy group, an optionally substituted alkylthio group,

[0011]

Embedded image A group, R ₂ and R ₃ are each independently a hydrogen atom or an alkyl group, R ₄ and R ₅ are each independently an alkyl group, R ₈ is a hydrogen atom, and n is 0 to 3 X is a halogen atom, an alkyl group, an alkoxy group or a haloalkoxy group, and A is C.
A compound having H or N is desirable, and R ₁ is a hydrogen atom; an alkyl group which may be substituted; an alkenyl group; an alkynyl group; an alkoxy group; an alkoxycarbonyl group; an alkylsulfonyl group or

[0012]

[Chemical 49] And G is a halogen atom; an optionally substituted alkyl group; an optionally substituted alkoxy group; an alkylthio group;

[0013]

Embedded image A group, R ₂ and R ₃ are each independently a hydrogen atom or an alkyl group, R ₄ and R ₅ are each independently an alkyl group, R ₈ is a hydrogen atom, and n is 0 or 1 And X and Y are each independently a halogen atom, an alkyl group or an alkoxy group, and A is CH or N, and R ₁ is a hydrogen atom; a halogen atom, an alkyl group, an alkoxy group, an alkylthio group. Group, an alkylcarbonyl group, an alkoxycarbonyl group, an alkylsulfinyl group, an alkylsulfonyl group, an alkyl group which may be substituted with at least one substituent selected from the group consisting of a phenyl group and a benzyloxy group; an alkenyl group; an alkynyl Group; alkoxy group; alkoxycarbonyl group; alkylsulfonyl group or

[0014]

[Chemical 51] And G is a halogen atom; an alkyl group optionally substituted by a halogen atom; an alkoxy group optionally substituted by a halogen atom; an alkylthio group;

[0015]

Embedded image A group, R ₂ and R ₃ are each independently a hydrogen atom or an alkyl group, R ₄ and R ₅ are each independently an alkyl group, R ₈ is a hydrogen atom, and n is 0 or 1 Particularly preferred is a compound in which X and Y are each independently a halogen atom, an alkyl group or an alkoxy group, and A is CH or N.

The salt of the pyridonesulfonylurea compound represented by the general formula (I) is sodium salt,
Examples thereof include alkali metal salts such as potassium salts, alkaline earth metal salts such as magnesium salts and calcium salts, or ammonium salts such as dimethylamine salts and triethylamine salts.

The pyridonesulfonylurea compound represented by the general formula (I) or a salt thereof (hereinafter abbreviated as the compound of the present invention) can be produced by the following method. The pyridonesulfonylurea compound can be produced, for example, by the method of the reactions [A] to [D],
The salt can be produced according to the reactions [A] to [D] and a usual method for producing a salt.

[0018]

Embedded image

In the reactions [A] to [D], Q, R ₈ , X, Y
And A are as described above, and R ₉ is an alkyl group or an aryl group. Examples of the alkyl group contained in R ₉ include an alkyl group having 1 to 6 carbon atoms which may be substituted with a halogen atom, an alkoxy group or the like, and the aryl group may be substituted with a chlorine atom, a methyl group or the like. Examples thereof include a good phenyl group and a naphthyl group. The halogen atom and the alkoxy group as the substituent are the same as those described in R ₁ .

The reaction [A] is carried out in the presence of a base,
Reactions [B], [C] and [D] are also carried out in the presence of a base, if necessary. As the base, a tertiary amine such as triethylamine, 1,8-diazabicyclo [5.
4.0] -7-undecene or the like is used.

The reactions [A], [B], [C] and [D] are carried out in the presence of a solvent, if necessary. As the solvent, aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; cyclic or non-cyclic aliphatic hydrocarbons such as chloroform, carbon tetrachloride, methylene chloride, dichloroethane, trichloroethane, hexane and cyclohexane; diethyl ether, Ethers such as dioxane and tetrahydrofuran; Nitriles such as acetonitrile, propionitrile and acrylonitrile;
Esters such as methyl acetate and ethyl acetate; polar aprotic solvents such as dimethyl sulfoxide, sulfolane and dimethylformamide, and the like.

The reaction temperature of the reaction [A] is usually -20 to +1.
00 ° C, preferably 0 to 40 ° C, and the reaction time is 0.
01 to 24 hours, preferably 0.1 to 1.5 hours, the reaction temperature of the reaction [B] is usually 0 to 150 ° C.,
The reaction time is 0.1 to 24 hours, the reaction temperature of the reaction [C] is usually 0 to 150 ° C, and the reaction time is 0.1 to 2 hours.
The reaction time of the reaction [D] is usually -20 to +
It is 150 ° C. and the reaction time is 0.1 to 24 hours.

The pyridone compound represented by (II-1) in the reactions [A] and [B] is a useful and novel intermediate compound for producing the compound of the present invention. It can be produced by a method such as [I]. The case where the pyridone ring contained in Q in the general formula (II-1) is α-pyridone type is described in the reaction [E], and the pyridone ring is α-pyridone type, and
The case where R ₁ is an alkoxy group is described in the reaction [F],
The case where the pyridone ring is a γ-pyridone type is described in reactions [G], [H] and [I].

[0024]

[Chemical 54]

[0025]

[Chemical 55]

[0026]

[Chemical 56]

[0027]

[Chemical 57]

[0028]

Embedded image

Of the compounds represented by (XIII) in the above reaction [E], the compound in which n is 1 and G is substituted at the 4-position of the pyridone ring can be prepared by the method as in the reaction [J]. Compounds represented by (XIII), wherein n is 1, G is substituted at the 5-position of the pyridone ring, and G is a halogen atom, can be prepared by the reaction [K]. It can be manufactured by any method.
Further, the compound represented by (VIII) in the above reaction [G] can also be produced by the method like the reaction [L].

[0030]

Embedded image

[0031]

Embedded image

The reaction conditions of each step in the reaction [H] are the same as those in the reaction [G]. Also, the reaction conditions of the steps in which the reaction conditions are not described in the reaction [I] are the same as those in the reaction [G].

In the reactions [E] to [L], R ₁ , G and n are as described above, T is a chlorine atom, bromine atom or iodine atom, M is lithium, sodium or potassium, and R is R. _1a is an alkyl group, R ₁₀ is a hydrogen atom or a benzyl group, G ₁ is a halogen atom, G ₂ is an alkylthio group, G ₃ is an alkyl group, an alkenyl group,
Alkynyl group, alkoxy group, alkylcarbonyl group,
Alkoxycarbonyl group, alkylsulfinyl group, alkylsulfonyl group,

[0034]

[Chemical formula 61] G ₄ is an alkoxy group, a haloalkoxy group or

[0035]

Embedded image G'is a halogen atom, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, a haloalkoxy group, an alkylthio group, an alkylcarbonyl group, an alkoxycarbonyl group, an alkylsulfinyl group, an alkylsulfonyl group,

[0036]

[Chemical formula 63] And R ₂ , R ₃ , R ₄ , R ₅ , R ₆ and R ₇ are the same as those described above. Further, ph is a phenyl group,
(T) each represents a tertiary butyl group.

As a catalyst which can be used in the step of producing (IV) from (V) in the reaction [E] and the step of producing (VIII) from (IX) in the reaction [G], copper chloride ( One or more of copper halides such as I) and (II), copper (I) and (II) bromide, and copper (I) and (II) iodide are appropriately selected. As the oxidant that can be used in the step of producing (VI) from (VII) in the reaction [E] and the step of producing (XIV) from (XII) in the reaction [F], hydrogen peroxide and peroxide can be used. One or more of acetic acid, metachloroperbenzoic acid and manganese dioxide are appropriately selected. Examples of the catalyst that can be used in the step of producing (X) from (XI) in the reaction [G] include dimethylformamide, and chlorinating agents that can be used in the step include phosphorus oxychloride, One type or two or more types are appropriately selected from phosphorus pentachloride, thionyl chloride and the like. As a catalyst that can be used in the step of producing (XV) from (XVI) in the reaction [G] and the catalytic reduction step of producing (XIII-a) in the reaction [J], palladium carbon, palladium chloride One kind or two or more kinds are appropriately selected from such palladium catalysts, platinum, platinum catalysts such as platinum oxide and the like. Step of producing (XVII) from (XVIII) in reaction [J], (XIII-b) to (XIII- in reaction [K]
(XX) to (VI) in the step [c] for producing c) and the reaction [L].
As the halogenating agent that can be used in the step of producing II), one kind or two or more kinds are appropriately selected from N-chlorosuccinimide, N-bromosuccinimide, fluorine, chlorine, bromine, iodine and the like. (XIII in the reaction [J]
-(A) is produced, (XX) to (XI in the reaction [L].
X) from (XIX) to (VII
As the organic acid that can be used in the step of producing I), one kind or two or more kinds are appropriately selected from boron trifluoride, acetic acid, trifluoroacetic acid, etc., and the mineral acid is hydrochloric acid, sulfuric acid, nitric acid. One kind or two or more kinds is appropriately selected from the above. As the inert gas which can be used in any step in the reactions [F], [I], [J] and [L], one kind or two kinds or more is appropriately selected from nitrogen, argon, helium and the like. .

Examples of the solvent or base that can be used in the reactions [E] to [L] include the followings. As the solvent, aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; cyclic or non-cyclic aliphatic hydrocarbons such as carbon tetrachloride, methylene chloride, chloroform, dichloromethane, dichloroethane, trichloroethane, hexane and cyclohexane. Ethers such as dioxane, tetrahydrofuran and diethyl ether; esters such as methyl acetate and ethyl acetate; polar aprotic solvents such as dimethyl sulfoxide, sulfolane, dimethylacetamide, dimethylformamide, N-methylpyrrolidone and pyridine; Nitriles such as acetonitrile, propionitrile and acrylonitrile; Ketones such as acetone and methyl ethyl ketone; Amines such as monomethylamine, dimethylamine and triethylamine ; Methanol,
One or more kinds are appropriately selected from alcohols such as ethanol, propanol and tertiary butanol; organic acids such as acetic acid; ammonia water; water and the like. Examples of the base include alkali metals such as sodium and potassium; alkali metal alcoholates such as sodium methylate, sodium ethylate and potassium tertiary butyrate; carbonates such as potassium carbonate and sodium carbonate; potassium bicarbonate; Bicarbonates such as sodium bicarbonate; metal hydroxides such as potassium hydroxide and sodium hydroxide; metal hydrides such as potassium hydride and sodium hydride; amines such as monomethylamine, dimethylamine and triethylamine. One or two or more kinds are appropriately selected from pyridines and pyridines such as 4-dimethylaminopyridine.

Among the compounds represented by (XII) in the reaction [E], compounds in which the —SO ₂ NH—Bu (t) group is substituted at the 2-position of the pyridine ring are compounds disclosed in European Patent Publication No. 562.
No. 731, pages 5 to 10, and the process of producing (X) from (XI) in the reaction [G] is performed by Anals Pharmaceuticals Francaisies. (Annales pharmace
utilique francaises), Volume 31,
No. 6, pp. 467-474, 1973.

The compound represented by (II-2) in the above reaction [C] can be produced, for example, by the following method [M], and (II-3) in the above reaction [D]. The compound represented by can be produced, for example, by the following method [N].

[0041]

[Chemical 64]

[0042]

Embedded image

In the reaction [N], R ₉ is as described above.
The compound of the present invention exhibits an excellent herbicidal effect when used as an active ingredient of a herbicide. Its application range is wide ranging from agricultural fields such as paddy fields, upland fields, orchards and mulberry fields to non-agricultural fields such as mountain forests, farm roads, grounds and factory sites, and soil treatment and foliage treatment can be appropriately selected.

Herbicides containing the compound of the present invention include, for example, grass weeds such as barnyardgrass, crabgrass, green locust, oak grass, oats, sorghum, sorghum, velvet millet, paragrass, azegaya, itazegaya, etc.
Kogomegayatsu, Hamaributa, Firefly, Mizugaya,
Cyperaceae weeds such as pearl oysters, pine nuts, kurowai, etc., Omodaka weeds such as Urikawa, Omodaka, Hera moda, etc. , Black-necked, Malaba morning glory, Shiroza, Sida,
It is possible to control harmful weeds such as broad-leaved, yellow-tailed squirrel, Ebisu grass, dog physalis, sandgrass, chickweed, lobster, rapeweed, phytokenosa, enokigusa, and other useful crops, so useful crops such as corn, soybean, cotton, wheat, rice, barley. , Oats, sorghum, canola, sunflower, sugar beet, sugar cane,
It is effectively used in the case of selectively controlling harmful weeds in the cultivation of grass, peanuts, flax, etc. or in the case of non-selectively controlling harmful weeds.

Herbicides containing the compound of the present invention are usually prepared by mixing the compound with various agricultural auxiliaries, and powders, granules,
Granule wettable powder, wettable powder, aqueous suspension, oily suspension, aqueous solvent, emulsion, tablets, capsules and the like are used by formulating, but as long as it is suitable for the purpose of the present invention, Any of the dosage forms used in the art can be used. As the auxiliary agent used in the preparation, a solid carrier such as diatomaceous earth, slaked lime, calcium carbonate, talc, white carbon, kaolin, bentonite, a mixture of kaolinite and sericite, clay, sodium carbonate, baking soda, mirabilite, zeolite and starch. Water, toluene, xylene, solvent naphtha, dioxane, acetone, isophorone,
Methyl isobutyl ketone, chlorobenzene, cyclohexane, dimethyl sulfoxide, dimethylformamide,
Solvents such as N-methyl-2-pyrrolidone and alcohol;
Fatty acid salt, benzoate, alkyl sulfosuccinate, dialkyl sulfosuccinate, polycarboxylate, alkyl sulfate ester salt, alkyl sulfate salt, alkyl aryl sulfate salt, alkyl diglycol ether sulfate salt, alcohol sulfate ester salt, alkyl sulfone Acid salt, alkylaryl sulfonate, aryl sulfonate, lignin sulfonate, alkyl diphenyl ether disulfonate, polystyrene sulfonate, alkyl phosphate ester salt, alkyl aryl phosphate, styryl aryl phosphate, polyoxy Ethylene alkyl ether sulfate ester salt, polyoxyethylene alkylaryl ether sulfate salt, polyoxyethylene alkylaryl ether sulfate ester salt, polyoxyethylene alkyl ether phosphate salt, Anionic surfactants and spreading agents such as oxyethylene alkylaryl phosphate ester salts and salts of naphthalene sulfonic acid formalin condensate; sorbitan fatty acid ester, glycerin fatty acid ester, fatty acid polyglyceride, fatty acid alcohol polyglycol ether, Acetylene glycol, acetylene alcohol, oxyalkylene block polymer, polyoxyethylene alkyl ether, polyoxyethylene alkylaryl ether, polyoxyethylene styryl aryl ether, polyoxyethylene glycol alkyl ether, polyoxyethylene fatty acid ester, polyoxyethylene sorbitan fatty acid ester , Polyoxyethylene glycerin fatty acid ester, polyoxyethylene hydrogenated castor oil, polyoxypropylene Nonionic surfactants and spreaders such as a fatty acid ester; olive oil,
Examples thereof include vegetable oils such as kapok oil, castor oil, palm oil, camellia oil, coconut oil, sesame oil, corn oil, rice bran oil, peanut oil, cottonseed oil, soybean oil, rapeseed oil, linseed oil, cutting oil, and liquid paraffin, and mineral oils. These auxiliary agents can be selected from those known in the art without departing from the object of the present invention. Further, various commonly used auxiliary agents such as a bulking agent, a thickening agent, an anti-settling agent, an antifreezing agent, a solvent, a dispersion stabilizer, a phytotoxicity reducing agent and an antifungal agent can also be used. The compounding ratio of the compound of the present invention to various auxiliary agents is 0.1: 99.9 to 95: 5, preferably 0.2: 99.8 to 85:15.

The application rate of the herbicide containing the compound of the present invention may be: weather conditions, soil conditions, formulation form, kind of target weed,
Although it cannot be specified unconditionally due to differences in application time and the like, generally, the compound of the present invention is 0.5 to 5000 per hectare.
g, preferably 1 to 1000 g, more preferably 5 to 5
Apply so that it will be 00g. The present invention also includes a method for controlling harmful weeds by applying such a herbicide.

Herbicides containing the compound of the present invention are
It can be mixed or used in combination with other pesticides, fertilizers, phytotoxicity-reducing agents, and the like, and in this case, it may show further excellent effects and actions. Other pesticides include herbicides, fungicides, antibiotics, plant hormones, insecticides and the like. In particular, one or two of the active ingredient compounds of the compound of the present invention and other herbicides.
A herbicidal composition containing a mixture of two or more species can improve the range of the species to be applied, the timing of drug treatment, herbicidal activity and the like in a preferable direction. The compounds of the present invention and the active ingredient compounds of other herbicides may be formulated separately, and may be mixed and used at the time of spraying, or both may be formulated and used together. The present invention also includes such a herbicidal composition.

The mixing ratio of the compound of the present invention to the active ingredient compound of other herbicides cannot be unconditionally defined due to differences in meteorological conditions, soil conditions, drug formulation, application period, application method, etc. 0.001 to 10000 parts by weight, and preferably 0.01 to 100 parts by weight, of the active ingredient compound of another herbicide is added to 1 part by weight. Further, the appropriate amount of application is 0.1 to 10000 g, preferably 0.2 to 50, as the total amount of active ingredient compounds per hectare.
It is 00 g. The present invention also includes a method for controlling harmful weeds by applying such a herbicidal composition.

Examples of the active ingredient compounds of other herbicides include the following (generic name). (1) 2,4-D, MCPA, MCPB, phenoxyacetic acid system such as naproanilide, 2,3,6-TBA, dicamba (dicamba)
a), aromatic carboxylic acids such as picloram, and other benazolines
n) and quinclorac, which are said to exhibit herbicidal activity by disturbing the auxin action of plants.

(2) Diuron, linuron, isoproturon (isop)
roturon), metobenzuron (methobenz)
Urea like uron, simazine
e), atrazine, atratone, simetry
n), promethrin, dimethamethrin, triazines such as metribuzin, bromacil, lenacyl.
uracils such as l), propanil (propani)
l), anilides such as cypromid, swep, carbamates such as phenmedipham, hydroxybenzonitriles such as bromoxynil, and other pyridates (others). pyridate),
Those which are said to exhibit herbicidal activity by inhibiting photosynthesis of plants such as bentazone.

(3) Quaternary ammonium salts such as paraquat and diquat, which are said to be free radicals themselves in plants to produce active oxygen and show a rapid herbicidal effect. system. (4) Nitrophen, chloromethoxyphen, chlomethoxyphen, bifenox, acifluorfen-sodium, diphenyl ethers such as homesafen, chlorphthal.
im), flumioxazin
e), full micro rack pentyl (flumiclor)
Cyclic imides such as ac-pentyl, and others, such as oxadiazon, sulfentrazone, thidiazimine, and the like, inhibit chlorophyll biosynthesis of plants and photosensitize peroxides to plants. It is said to exhibit herbicidal activity by abnormally accumulating in the body.

(5) Norflurazone
zon), metflurazon
Pyridazinone series, such as pyrazolate
plate), pyrazoxifene
n), pyrazoles such as benzophenap, and other fluridones
ne), flutamone, diflufenican, methoxyphenone, clomazone, sulcotrione.
otrione), isoxaflutole (isoxaf)
It is said to inhibit the pigment biosynthesis of plants such as carotenoids such as cultivated cultivated cultivated cultivars) and show a herbicidal effect characterized by a whitening effect.

(6) Diclofop-methyl (diclof)
op-methyl), pyriphenop sodium salt (pyriphenop-sodium), fluazifop-butyl (fluazifop-butyl), haloxyfop-methyl (haloxyfop-methyl).
l), quizalofop-e
tyl), cyhalofop-butyl (cyhalofop)
-Aryloxyphenoxypropionic acid system, such as alloxydim sodium salt (alloxy)
dim-sodium, crethodim
im), setoxydim, tralkoxydim, and other cyclohexanedione-based compounds that are strongly recognized to have a herbicidal effect specifically on grasses.

(7) Chlorimuron Ethyl
muron-ethyl), sulfometuron methyl (s
ulfumeturon-methyl), primisulfuron-meth
yl), bensulfuron-methyl (bensulfuro)
n-methyl), chlorsulfuron (chlors)
ulfuron), metsulfuron-methyl (metsu
lfuron-methyl), cynosulfuron (ci)
nosulfuron), pyrazosulfuron-ethyl (p
yrazosulfuron-ethyl), azimsulfuron, flazasulfuron, rimsulfuron, nicosulfuron (ni)
cosulfuron), imazosulfuron (imaz)
osulfuran), cyclosulfamuron (cyc)
Losulfamuron), Prosulfuron (pro
sulfuron), flupyrsulfuron (flupy)
rsulfuron), trisulfuron methyl (tri
sulfuron-methyl, sulfonylureas such as halosulfuron, trimetlopyrimidine sulfonamides such as flumetsulam, metsulam, imazapyr.
r), imazethapyr, imazaquin, imazamox
azamox), imidazolinones such as imazameth, pyrithiobac-sodium, bispyribac-sodium.
um), pyriminobac methyl
c-methyl), pyrimidinyl salicylic acid-based compounds, and other glyphosate ammonium salts (glypho)
state-ammonia), glyphosate-isopropylamine salt (glyphosate-isoprop)
ylamine), glufosinate ammonium salt (glufosinate-ammonium), bialaphos and the like, which are said to exhibit herbicidal activity by inhibiting amine acid biosynthesis in plants.

(8) Trifluralin
lin), oryzalin (nitralin), pendimethalin (pend)
dinitroaniline-based compounds such as imethalin, amiprophos-methyl
l), butamifos, anilofos, piperophos
os) such as organophosphorus compounds, chlorpropham (chl
or phenyl, phenyl carbamate system such as barban, daimuron (daimu)
ron), cumyluron, cumylamines such as bromobutide, ashram, and dithiopyr (dithiopyr), which are said to exhibit herbicidal activity by inhibiting cell mitosis. What is there.

(9) EPTC, butyrate (butyl)
ate), molinate, dimepiperate, esprocarb, thiobencarb
encarb), pyributyric (pyributic)
arb), thiocarbamate system, alaclor, butachlor
or), pretilachlor (pretilachlo)
r), metolachlor, tenylchlor, chloroacetamide-based compounds such as dimethenamide, and other ethobenza
It is said to exhibit herbicidal activity by inhibiting protein biosynthesis or lipid biosynthesis of plants such as medeacet, mefenacet, thiafluamide, tridiphane, and cafenstrol. thing.

[0057]

EXAMPLES Examples of the present invention will be described below, but the present invention is not limited thereto. First, a synthesis example of the compound of the present invention will be described.

Synthesis Example 1 N-[(4,6-dimethoxypyrimidin-2-yl) aminocarbonyl]-[1- (n-propyl) -2 (1
H) -pyridone] -3-sulfonamide (compound N below)
o. Synthesis of 21) (1) 3-amino-2-chloropyridine (50.5 g), hydrochloric acid (100 ml) and acetic acid (40 ml) are mixed, and an aqueous solution 1 containing sodium nitrite (29.5 g) at 5 ° C or lower with stirring is added thereto.
After dropping 00 ml, the mixture was reacted at the same temperature for 1 hour. The obtained suspension was added little by little to 400 ml of acetic acid containing 3 g of cupric chloride and 75 g of sulfurous acid gas under stirring at 0 ° C. and then reacted at the same temperature for 30 minutes to give 2-chloro-3-chlorosulfonylpyridine. A reaction mixture containing was obtained.

Water was added to the obtained reaction mixture, which was then extracted with methylene chloride. Then, the extraction layer was washed with water thoroughly and dried over anhydrous sodium sulfate, and 62 g of tert (tertiary) -butylamine was added dropwise at room temperature, and then 30 minutes at the same temperature.
Let react for minutes. After the reaction was completed, the reaction mixture was filtered, and methylene chloride was distilled off from the obtained filtrate under reduced pressure to give a melting point of 134.
3-tert-butylaminosulfonyl at -135 ° C
67.6 g of 2-chloropyridine was obtained.

(2) 20 g of 3-tert-butylaminosulfonyl-2-chloropyridine, 20 potassium hydroxide
g and tert-butyl alcohol (150 ml) were mixed and reacted in an autoclave at 140 ° C. overnight. After completion of the reaction, the reaction mixture was allowed to cool, poured into water, and acidified with hydrochloric acid. Then, the mixture was extracted with methylene chloride, the extracted layer was dried over anhydrous sodium sulfate, and methylene chloride was distilled off under reduced pressure. The crystals obtained are washed with methanol to give a melting point of 220-
222 ° C 3-tert-butylaminosulfonyl-2
14.3 g of (1H) -pyridone was obtained.

(3) 3-tert-Butylaminosulfonyl-2 (1H) -pyridone 600 mg, n (normal) -propyl iodide 530 mg, anhydrous potassium carbonate 72
Mix 0 mg and 20 ml of dimethylformamide,
The reaction was carried out at 0 to 100 ° C for 1.5 hours. After completion of the reaction, water was added to the reaction mixture, and then hydrochloric acid was added to acidify the mixture.
Then, the mixture was extracted with methylene chloride, the extracted layer was dried over anhydrous sodium sulfate, and methylene chloride was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (developing solvent; ethyl acetate: hexane = 1: 1), melting point 11
1- (n-propyl) -3-tert- at 8-120 ° C
Butylaminosulfonyl-2 (1H) -pyridone 580
mg was obtained.

(4) 1- (n-propyl) -3-ter
t-Butylaminosulfonyl-2 (1H) -pyridone 5
80 mg and 3 ml of trifluoroacetic acid were mixed and reacted at room temperature overnight. After completion of the reaction, trifluoroacetic acid was distilled off from the reaction mixture under reduced pressure, the obtained residue was washed with diethyl ether, and 1- (n-propyl) -3-aminosulfonyl-2 (1H having a melting point of 140 to 142 ° C was used. ) -Pyridone (intermediate product No. 4 described later) (326 mg) was obtained.

(5) 320 mg of 1- (n-propyl) -3-aminosulfonyl-2 (1H) -pyridone, phenyl N- (4,6-dimethoxypyrimidin-2-yl)
330 mg of carbamate and 10 ml of anhydrous dimethylformamide were mixed, and 218 mg of 1,8-diazabicyclo [5.4.0] -7-undecene was added thereto, followed by reaction at room temperature for 30 minutes. After completion of the reaction, the reaction mixture was put into water, the insoluble material was filtered off, and the mixture was made weakly acidic with concentrated hydrochloric acid. After that, the precipitated crystals are collected by filtration and dried to give a melting point of 180-
312 mg of the target product at 183 ° C was obtained.

Synthesis Example 2 N-[(4,6-dimethoxypyrimidin-2-yl) aminocarbonyl]-[1-methyl-2 (1H) -pyridone] -6-sulfonamide (Compound No. 287 described later).
Synthesis of (1) 2-tert-butylaminosulfonyl-6-chloropyridine 5 g, potassium hydroxide 5 g and tert-
Mix 50 ml of butanol, and mix in an autoclave for 150
The reaction was carried out at 0 ° C for 3 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, poured into water, and extracted with ethyl acetate. The obtained extract layer was dried over anhydrous sodium sulfate, and ethyl acetate was distilled off under reduced pressure to give 6-tert with a melting point of 197 to 198 ° C.
-Butylaminosulfonyl-2 (1H) -pyridone 3.
9 g was obtained.

(2) 350 mg of sodium metal dissolved in 5 ml of methanol, 2.3 g of 6-tert-butylaminosulfonyl-2 (1H) -pyridone and 2 ml of dimethylsulfate were mixed and reacted at room temperature for 30 minutes. . After completion of the reaction, the reaction mixture was put into water and extracted with ethyl acetate. The obtained extract layer was dried over anhydrous sodium sulfate, ethyl acetate was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent; ethyl acetate: hexane = 4: 1) to give a melting point of 135-136 ° C. 1
-Methyl-6-tert-butylaminosulfonyl-2
400 mg of (1H) -pyridone was obtained.

(3) 300 mg of 1-methyl-6-tert-butylaminosulfonyl-2 (1H) -pyridone and 1 ml of trifluoroacetic acid were mixed and reacted under reflux for 6 hours. After completion of the reaction, trifluoroacetic acid was distilled off from the reaction mixture under reduced pressure, the obtained residue was washed with diethyl ether and dried to give 1-methyl-6-mp of melting point 177-178 ° C.
Aminosulfonyl-2 (1H) -pyridone (intermediate body No. 195 described below) (150 mg) was obtained.

(4) 1-Methyl-6-aminosulfonyl-2 (1H) -pyridone 100 mg, phenyl N-
(4,6-Dimethoxypyrimidin-2-yl) carbamate (150 mg) and acetonitrile (5 ml) were mixed, to which 1,8-diazabicyclo [5.4.0] -7-undecene (100 mg) was added, and the mixture was reacted at room temperature for 30 minutes. It was After completion of the reaction, the reaction mixture was put into ice water and weakly acidified with hydrochloric acid. The precipitated crystals were collected by filtration, washed with water and dried to obtain 130 mg of the desired product having a melting point of 162-165 ° C.

Synthesis Example 3 N-[(4,6-dimethoxypyrimidin-2-yl) aminocarbonyl]-[1-methyl-4 (1H) -pyridone] -3-sulfonamide (Compound No. 313 described below)
(1) 80 g of phosphorus pentachloride, 80 g of phosphorus oxychloride and 4
-Hydroxy-3-pyridinesulfonic acid 20 g was mixed and reacted under reflux for 4.5 hours to obtain a reaction mixture containing 4-chloro-3-chlorosulfonylpyridine.

Excess phosphorus oxychloride was distilled off under reduced pressure from the obtained reaction mixture, the residue was put into about 200 g of ice, and the mixture was extracted with dichloromethane. The obtained extracted layer was washed with saturated saline, dried over anhydrous sodium sulfate, cooled with ice, and then 20.8 g of tert-butylamine was added dropwise at 25 ° C or lower, and the mixture was reacted overnight at room temperature. After completion of the reaction, ice water was added to the reaction mixture to separate the layers, and the aqueous layer was extracted with dichloromethane. The obtained dichloromethane layer was combined with the organic layer, washed with saturated brine, and dried over anhydrous sodium sulfate.
After that, dichloromethane is distilled off and the melting point is 126 to 132 ° C.
12.8 g of 3-tert-butylaminosulfonyl-4-chloropyridine was obtained.

(2) 3-tert-butylaminosulfonyl-4-chloropyridine (4.97 g), potassium hydroxide (5.0 g) and tert-butanol (50 ml) were mixed,
The reaction was carried out in an autoclave at 140 ° C for 2 hours. After completion of the reaction, tert-butanol was distilled off from the reaction mixture,
Ice was added and the mixture was neutralized with concentrated hydrochloric acid. This was extracted with dichloromethane, the extract layer was washed with saturated brine and dried over anhydrous sodium sulfate. Then distill off dichloromethane,
The yellow solid obtained is washed with diethyl ether and mp 2
3-tert-butylsulfonyl-4 at 05-215 ° C
3.54 g of (1H) -pyridone was obtained.

(3) 3-tert-butylsulfonyl-
1.15 g of 4 (1H) -pyridone, 5 ml of dimethylformamide, 0.73 g of potassium carbonate and 1.84 g of iodomethane were mixed and reacted at 80 ° C. for 7 hours in an autoclave. After completion of the reaction, dimethylformamide was distilled off from the reaction mixture under reduced pressure, ice water was added thereto, and the mixture was extracted with dichloromethane. The obtained extracted layer was washed with saturated saline and dried over anhydrous sodium sulfate, and dichloromethane was distilled off. The obtained residue is chromatographed on silica gel (developing solvent; methanol: dichloromethane = 3: 97).
And 1-methyl-3-t, mp 183-185 ° C.
1.16 g of ert-butylaminosulfonyl-4 (1H) -pyridone were obtained.

(4) 1-Methyl-3-tert-butylaminosulfonyl-4 (1H) -pyridone (1.0 g) and trifluoroacetic acid (10 ml) were mixed and reacted under reflux for 3 hours. After completion of the reaction, trifluoroacetic acid was distilled off from the reaction mixture under reduced pressure, and the obtained residue was crystallized with diethyl ether. The crystals were washed with diethyl ether to give 1-methyl-3-aminosulfonyl-4 (1H) -pyridone having a melting point of 216 ° C. (decomposition) (intermediate body No. 2 described later).
06) 0.71 g was obtained.

(5) 1-Methyl-3-aminosulfonyl-4 (1H) -pyridone 226 mg, phenyl N-
(4,6-Dimethoxypyrimidin-2-yl) carbamate (360 mg) and anhydrous acetonitrile (3 ml) were mixed, and 1,8-diazabicyclo [5.4.0] -7 was added thereto.
-After adding 200 mg of undecene, it was made to react at room temperature for 1.5 hours. After completion of the reaction, water was added to the reaction mixture, and concentrated hydrochloric acid was added thereto until it became acidic. The precipitated crystals are collected by filtration,
Wash with water, dry, then wash with ethyl acetate, melting point 161 ° C
237 mg of the target product of (decomposition) was obtained.

Synthesis Example 4 N-[(4,6-dimethoxypyrimidin-2-yl) aminocarbonyl]-[1-ethoxy-2 (1H) -pyridone] -3-sulfonamide (Compound No. 95 described later)
Synthesis of (1) Acetic acid (50 ml), 3-tert-butylaminosulfonyl-2-chloropyridine (5 g) and hydrogen peroxide solution (25)
ml was added, and the mixture was reacted at 100 ° C. for 1 hour with stirring.
After that, 25 ml of hydrogen peroxide water was added twice at 1 hour intervals at the same temperature to carry out a reaction for 2 hours, and then at the same temperature for another 2 hours. After completion of the reaction, the reaction mixture was allowed to cool and put into water. Then, the mixture was extracted with methylene chloride, the extracted layer was dried over anhydrous sodium sulfate, and methylene chloride was distilled off under reduced pressure. The obtained crystal was washed with a mixed solvent of n-hexane and ethyl acetate to obtain 3 g of 3-tert-butylaminosulfonyl-2-chloropyridine N-oxide.

(2) 250 mg of sodium metal was added to 50 ml of dried ethanol, and the mixture was stirred under a nitrogen atmosphere. After the metallic sodium is completely dissolved, 3-tert
-Butylaminosulfonyl-2-chloropyridine N-
2.5 g of oxide was added, and the mixture was reacted under heating and reflux for 1 hour. After completion of the reaction, the reaction mixture is allowed to cool and put into water,
Acidified with hydrochloric acid. Then, the mixture was extracted with ethyl acetate, the extracted layer was dried over anhydrous sodium sulfate, and ethyl acetate was distilled off under reduced pressure. The obtained residue is subjected to silica gel column chromatography (developing solvent; ethyl acetate: n-hexane = 2:
Purification in 1) gave 1-ethoxy-3-tert-butylaminosulfonyl-2 (1H) -pyridone (1.5 g). (3) 1-Ethoxy-3-te obtained in (2) above
Using rt-butylaminosulfonyl-2 (1H) -pyridone, according to Synthesis Example 1 (4) and (5) above, 90 mg of the desired product having a melting point of 180 to 182 ° C was obtained.

Synthesis Example 5 N-[(4,6-dimethoxypyrimidin-2-yl) aminocarbonyl]-[1-ethyl-4-ethoxy-2
Synthesis of (1H) -pyridone] -3-sulfonamide (Compound No. 496 described below) (1) 11.2 g of 60% sodium hydride was washed with n-hexane, 250 ml of dimethylformamide was added,
Stir to homogenize under nitrogen atmosphere. A solution prepared by dissolving 30 g of benzyl alcohol in 50 ml of dimethylformamide was gradually added dropwise thereto under cooling, and the mixture was stirred at room temperature for 3 hours. Then, 20 g of 3-tert-butylaminosulfonyl-2-chloropyridine was added under cooling, and the mixture was stirred at room temperature for 2 hours.
The reaction was carried out under stirring for one day. After completion of the reaction, the reaction mixture was poured into water and acidified with hydrochloric acid. The precipitated crystals are collected by filtration,
Washed with distilled water. The crystals obtained are dried, melting point 10
21 g of 3-tert-butylaminosulfonyl-2-benzyloxypyridine having a temperature of 7 to 108 ° C. was obtained.

(2) 3 to 200 ml of tetrahydrofuran
Dissolve 10 g of -tert-butylaminosulfonyl-2-benzyloxypyridine, cool to -70 ° C, n
-Butyl lithium 40 ml was added slowly. Thereafter, the mixture was reacted at the same temperature for 30 minutes under stirring, 8.5 g of N-chlorosuccinimide was added, and then the mixture was further reacted for 1 hour under stirring while maintaining the same temperature, and gradually returned to room temperature to complete the reaction. After completion of the reaction, the reaction mixture was put into water and extracted with ethyl acetate. The extract layer was dried over anhydrous sodium sulfate, and ethyl acetate was distilled off under reduced pressure. The obtained residue is purified by silica gel column chromatography (developing solvent; n-hexane: ethyl acetate = 3: 1), melting point 121-
6 g of 4-chloro-3-tert-butylaminosulfonyl-2-benzyloxypyridine at 122 ° C. was obtained.

(3) 800 mg of sodium metal was added to 150 ml of ethanol, and the mixture was stirred at room temperature under a nitrogen atmosphere. After the sodium metal was completely dissolved, under cooling,
Chloro-3-tert-butylaminosulfonyl-2-
Benzyloxypyridine (5 g) was added, and the mixture was reacted under heating under reflux for 3 hours. After completion of the reaction, the reaction mixture was allowed to cool, poured into water, and acidified with hydrochloric acid. Then, the mixture was extracted with ethyl acetate, the extracted layer was dried over anhydrous sodium sulfate, and ethyl acetate was distilled off under reduced pressure. The obtained crystals were washed with a mixed solvent of n-hexane and ethyl acetate to obtain 4 g of 4-ethoxy-3-tert-butylaminosulfonyl-2-benzyloxypyridine having a melting point of 112 to 114 ° C.

(4) 4-ethoxy-3-tert-butylaminosulfonyl-2-benzyloxypyridine (3 g) and a catalytic amount of palladium chloride were added to 100 ml of methanol, and the mixture was reacted under hydrogen gas atmosphere at room temperature for 5 hours with stirring. It was After completion of the reaction, the reaction mixture was filtered, and the solvent was distilled off from the obtained filtrate under reduced pressure. The crystals obtained were washed with a mixed solvent of n-hexane and ethyl acetate to give a melting point of 159.
Obtained 2.2 g of 4-ethoxy-3-tert-butylaminosulfonyl-2 (1H) -pyridone at ˜163 ° C.

(5) Acetonitrile 20 ml, anhydrous potassium carbonate 600 mg, 4-ethoxy-3-tert-butylaminosulfonyl-2 (1H) -pyridone 500 m
g and ethyl iodide 400 mg are mixed, and 80-100
The reaction was carried out at ℃ for 1.5 hours. After the reaction was completed, water was added to the reaction mixture. After adding hydrochloric acid to acidify the mixture, the mixture was extracted with ethyl acetate, the extract layer was dried over anhydrous sodium sulfate, and ethyl acetate was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (developing solvent; ethyl acetate: n-hexane = 1: 1), melting point 119-1.
350 m of 1-ethyl-4-ethoxy-3-tert-butylaminosulfonyl-2 (1H) -pyridone at 21 ° C.
g was obtained. (6) 1-Ethyl-4-ethoxy-3-tert-butylaminosulfonyl-2 (1) obtained in the above (5)
H) -pyridone is used, and the above Synthesis Examples 1 (4) and (5) are used.
According to the above, 100 mg of the desired product having a melting point of 168 to 171 ° C. was obtained.

Synthesis Example 6 N-[(4,6-dimethoxypyrimidin-2-yl) aminocarbonyl]-[1-ethyl-4-methylthio-2]
Synthesis of (1H) -pyridone] -3-sulfonamide (Compound No. 497 described below) (1) 3-tert-butylaminosulfonyl-2-benzyloxypyridine 6 in 60 ml of tetrahydrofuran
g, cooled to -70 ° C under a nitrogen atmosphere, and n-
Butyllithium 16 ml was gradually added. Thereafter, the mixture was reacted at the same temperature for 30 minutes under stirring, 2.3 g of dimethyl disulfide was added, and then the mixture was gradually stirred and returned to room temperature to react, and when the temperature was returned to room temperature, the reaction was terminated. After completion of the reaction, the reaction mixture was put into water and extracted with ethyl acetate. The extract layer was dried over anhydrous sodium sulfate, and ethyl acetate was evaporated under reduced pressure. The obtained residue is purified by silica gel column chromatography (developing solvent; n-hexane: ethyl acetate = 3: 1), and the melting point of 130-131 ° C. 4-
Methylthio-3-tert-butylaminosulfonyl-
5.7 g of 2-benzyloxypyridine was obtained.

(2) 4-Methylthio-3-tert-butylaminosulfonyl-2 in 20 ml of diethyl ether
-2.5 g of benzyloxypyridine was added and well dispersed, and then 10% of 47% boron trifluoride diethyl ether solution was added.
1 was added, and the mixture was reacted at 40 ° C. for 5 hours with stirring. After completion of the reaction, the reaction mixture was poured into water and extracted with ethyl acetate,
The extract layer was dried over anhydrous sodium sulfate, and ethyl acetate was evaporated under reduced pressure. The obtained crystals were washed with a mixed solvent of n-hexane and ethyl acetate to obtain 1.4 g of 4-methylthio-3-tert-butylaminosulfonyl-2 (1H) -pyridone having a melting point of 235 to 237 ° C.

(3) 10 ml of acetonitrile, 300 mg of anhydrous potassium carbonate and 4-methylthio-3-tert
-Butylaminosulfonyl-2 (1H) -pyridone 30
0 mg was mixed and reacted at 80 to 100 ° C. for 30 minutes. Then, 240 mg of ethyl iodide was added, and the mixture was reacted at the same temperature for 30 minutes. After completion of the reaction, the reaction mixture was poured into water, hydrochloric acid was added to acidify the mixture, and the mixture was extracted with ethyl acetate. After drying the extract layer with anhydrous sodium sulfate,
The ethyl acetate was distilled off under reduced pressure. The obtained residue is subjected to silica gel column chromatography (developing solvent; ethyl acetate: n
-Purified with hexane = 1: 1), melting point 207-210 ° C
210 mg of 1-ethyl-4-methylthio-3-tert-butylaminosulfonyl-2 (1H) -pyridone were obtained. (4) 1-Ethyl-4-methylthio-3-tert-butylaminosulfonyl-2 (1 obtained in (3) above.
H) -pyridone is used, and the above Synthesis Examples 1 (4) and (5) are used.
According to the above, 100 mg of the target product having a melting point of 204 to 205 ° C. was obtained.

Synthesis Example 7 N-[(4,6-dimethoxypyrimidin-2-yl) aminocarbonyl]-[1- (n-propyl) -5-bromo-2 (1H) -pyridone] -3-sulfonamide (Synthesis of Compound No. 503) (1) 3-tert-Butylaminosulfonyl-2 (1H) -pyridone (500 mg) and N in chloroform (30 ml).
-Bromosuccinimide (426 mg) was added, and the mixture was reacted under heating and reflux for 18 hours. After completion of the reaction, the reaction mixture was allowed to cool and filtered. The solvent was distilled off under reduced pressure from the obtained filtrate,
5-Bromo-3-tert-butylaminosulfonyl-
759 mg of 2 (1H) -pyridone was obtained.

(2) 10 ml of acetonitrile, 600 mg of anhydrous potassium carbonate and 5-bromo-3-tert-butylaminosulfonyl-2 (1H) -pyridone 754 m
g was mixed and reacted at 80 to 100 ° C. for 30 minutes. Then, 404 mg of ethyl iodide was added, and the mixture was reacted at the same temperature for 30 minutes. After completion of the reaction, the reaction mixture was poured into water, hydrochloric acid was added to acidify the mixture, and the mixture was extracted with methylene chloride. After the extract layer was dried over anhydrous sodium sulfate, methylene chloride was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 317 mg of 1- (n-propyl) -5-bromo-3-tert-butylaminosulfonyl-2 (1H) -pyridone. (3) 1- (n-propyl) -obtained in (2) above
5-Bromo-3-tert-butylaminosulfonyl-
2 (1H) -pyridone was used, and the target compound 280 having a melting point of 200 to 210 ° C. was used according to the above-mentioned Synthesis Examples 1 (4) and (5).
mg was obtained.

Synthesis Example 8 N-[(4-Methoxy-6-methyl-1,3,5-triazin-2-yl) aminocarbonyl]-[2-chloro-1-methyl-4 (1H) -pyridone] Synthesis of -3-sulfonamide (Compound No. 676 described below) (1) 16.6 g of benzyl alcohol was dissolved in 160 ml of anhydrous dimethylformamide, and the mixture was cooled with ice, and then 10
At 16 ° C. or lower, 6.16 g of 60% sodium hydride was added little by little, and after completion of the addition, the mixture was stirred at room temperature for 20 minutes. Then, the mixture was ice-cooled again, 20.8 g of 2,4-dichloropyridine was added little by little, and after completion of the addition, the mixture was reacted at room temperature for 2 hours with stirring. After completion of the reaction, the reaction mixture was cooled with ice and neutralized with concentrated sulfuric acid. Then, dimethylformamide was distilled off under reduced pressure, water was added to the residue, and the mixture was extracted with dichloromethane. The extract was washed with brine and dried over anhydrous sodium sulfate,
Dichloromethane was distilled off to obtain 24.4 g of yellow crystalline 4-benzyloxy-2-chloropyridine.

(2) Under a nitrogen atmosphere, 90 ml of an anhydrous tetrahydrofuran solution containing 10 g of 4-benzyloxy-2-chloropyridine was cooled to -73 ° C. using dry ice-acetone. 37 ml of 1.7 M butyllithium hexane solution was added dropwise thereto at −66 ° C. or lower, and after completion of the addition, the mixture was reacted at the same temperature for 15 minutes while stirring. Then
4.1 g of sulfur powder was added, the mixture was further stirred at the same temperature for 10 minutes, gradually returned to room temperature, and reacted under stirring for 1.2 hours.

After completion of the reaction, ice was added to the reaction mixture, the mixture was acidified with concentrated hydrochloric acid, and then extracted with dichloromethane to obtain an extract containing 4-benzyloxy-2-chloro-3-pyridinethiol. 90 ml of 50% acetic acid was added to the obtained extract.
Was added and the reaction was carried out while blowing chlorine gas at 5 ° C. or lower, and the reaction was terminated when excess chlorine gas began to come out.
After completion of the reaction, ice was added to the reaction mixture, extracted with dichloromethane, washed twice with ice water, and dried over anhydrous sodium sulfate to obtain an extract containing 4-benzyloxy-2-chloro-3-chlorosulfonylpyridine. It was The obtained extract was ice-cooled, and tert-butylamine 20 m
1 was dropped, and then the mixture was returned to room temperature and reacted for 30 minutes under stirring. After completion of the reaction, water was added to the reaction mixture, extracted with dichloromethane, washed with brine and dried over anhydrous sodium sulfate, and then dichloromethane was distilled off under reduced pressure. The obtained residue is subjected to silica gel column chromatography (developing solvent;
Purification with ethyl acetate: n-hexane = 2: 3) gave 0.89 g of 4-benzyloxy-2-chloro-3-tert-butylaminosulfonylpyridine.

(3) 4-benzyloxy-2-chloro-
3-tert-butylaminosulfonylpyridine 0.8
2. To 20 ml of an ethanol solution containing 6 g, 10 mg of 10% palladium-carbon was added, and the mixture was added at 50 ° C. under a hydrogen gas atmosphere at 3.
The reaction was carried out for 5 hours. After completion of the reaction, palladium carbon was filtered off, and the obtained filtrate was evaporated under reduced pressure to give 2-chloro-3-t.
0.77 g of ert-butylaminosulfonyl-4 (1H) -pyridone was obtained.

(4) 2-chloro-3 in the autoclave
-Tert-Butylaminosulfonyl-4 (1H) -pyridone 0.32 g, acetonitrile 6 ml, potassium carbonate 0.36 g and iodomethane 0.37 g were added, and 90
The reaction was carried out at ℃ for 1.5 hours. After completion of the reaction, the reaction mixture was concentrated under reduced pressure, water was added, the mixture was extracted with ethyl acetate, washed with brine, dried over anhydrous sodium sulfate, and ethyl acetate was evaporated under reduced pressure. Diethyl ether was added to the obtained residue, and the mixture was crystallized by rubbing with a spatula to give 0.23 g of white crystalline 2-chloro-1-methyl-3-tert-butylaminosulfonyl-4 (1H) -pyridone. Obtained.

(5) 2-chloro-1-methyl-3-te
1.0 g of trifluoroacetic acid was added to 0.23 g of rt-butylaminosulfonyl-4 (1H) -pyridone to give 60
The reaction was allowed to stir overnight at ~ 70 ° C. After completion of the reaction, trifluoroacetic acid was distilled off under reduced pressure. Diethyl ether was added to the obtained residue and crystallized by rubbing with a spatula to give 2-chloro-1-methyl-3-aminosulfonyl-4 (1H) -pyridone having a melting point of 185 to 197 ° C. .517) 0.149 g was obtained. (6) Using 2-chloro-1-methyl-3-aminosulfonyl-4 (1H) -pyridone obtained in (5) above, according to Synthesis Example 3 (5) above, melting point 140-147.
0.163 g of the target product at 0 ° C was obtained.

Next, the first representative example of the pyridone compound of the present invention represented by the above general formula (II-1), which is synthesized according to the above-mentioned synthesis examples or the various methods for producing the present invention compound, will be described. Tables 7 to 7 and representative examples of the pyridonesulfonylurea compounds of the present invention represented by the general formula (I) are shown in Tables 8 to 14, respectively.

[0093]

[Table 1]

[0094]

[Table 2]

[0095]

[Table 3]

[0096]

[Table 4]

[0097]

[Table 5]

[0098]

[Table 6]

[0099]

[Table 7]

[0100]

[Table 8]

[0101]

[Table 9]

[0102]

[Table 10]

[0103]

[Table 11]

[0104]

[Table 12]

[0105]

[Table 13]

[0106]

[Table 14]

[0107]

[Table 15]

[0108]

[Table 16]

[0109]

[Table 17]

[0110]

[Table 18]

[0111]

[Table 19]

[0112]

[Table 20]

[0113]

[Table 21]

[0114]

[Table 22]

[0115]

[Table 23]

[0116]

[Table 24]

[0117]

[Table 25]

[0118]

[Table 26]

[0119]

[Table 27]

[0120]

[Table 28]

[0121]

[Table 29]

[0122]

[Table 30]

[0123]

[Table 31]

[0124]

[Table 32]

[0125]

[Table 33]

[0126]

[Table 34]

[0127]

[Table 35]

[0128]

[Table 36]

[0129]

[Table 37]

[0130]

[Table 38]

[0131]

[Table 39]

[0132]

[Table 40]

[0133]

[Table 41]

[0134]

[Table 42]

[0135]

[Table 43]

[0136]

[Table 44]

[0137]

[Table 45]

[0138]

[Table 46]

[0139]

[Table 47]

[0140]

[Table 48]

[0141]

[Table 49]

[0142]

[Table 50]

[0143]

[Table 51]

[0144]

[Table 52]

[0145]

[Table 53]

[0146]

[Table 54]

[0147]

[Table 55]

[0148]

[Table 56]

[0149]

[Table 57]

[0150]

[Table 58]

[0151]

[Table 59]

[0152]

[Table 60]

[0153]

[Table 61]

[0154]

[Table 62]

[0155]

[Table 63]

[0156]

[Table 64]

[0157]

[Table 65]

[0158]

[Table 66]

[0159]

[Table 67]

[0160]

[Table 68]

[0161]

[Table 69]

[0162]

[Table 70]

[0163]

[Table 71]

[0164]

[Table 72]

[0165]

[Table 73]

[0166]

[Table 74]

[0167]

[Table 75]

[0168]

[Table 76]

[0169]

[Table 77]

[0170]

[Table 78]

[0171]

[Table 79]

[0172]

[Table 80]

[0173]

[Table 81]

[0174]

[Table 82]

[0175]

[Table 83]

Next, test examples of the present invention will be described. Test Example 1 Upland soil was filled in a 1 / 150,000 hectare pot and seeds of various plants were sown. After that, the plant has a certain leaf age ((1) Novier 1.7-2.5 leaf stage, (2) Mekishiba 1.0-2.2 leaf stage, (3) Aobayu 0.1-1.0 leaf stage. , (4) Sida 0.1 to 1.2 leaf stage, (5)
Malva morning glory 0.2-2.0 leaf stage, (6) Ona fir 0.
3 to 1.8 leaf stage, (7) rice 1.2 to 2.2 leaf stage, (8) wheat 2.2 to 3.3 leaf stage, (9) corn 2.2.
3.4 leaf stage, (10) soybean primary leaf to 0.2 leaf stage), when the wettable powder prepared by the compound of the present invention according to the usual formulation method is weighed so as to have a predetermined active ingredient amount And diluted to 500 liters of water per hectare. Further, 0.1% by volume of agricultural spreading agent was added to the diluted solution, and the leaves were treated with a small spray. The growth state of various plants was visually observed 18 to 23 days after the chemical treatment, and 0 (equivalent to the untreated group) to
The herbicidal effect was evaluated based on the weeding rate (%) of 100 (complete withering), and the results shown in Table 15 were obtained.

[0177]

[Table 84]

[0178]

[Table 85]

Test Example 2 A paddy soil was filled in a 1,000,000 hectare pot, seeds of Nobie and firefly were sown, and the soil was lightly covered therewith. After that, it was left standing in a greenhouse at a water depth of 0.5 to 1 cm, and two days later, tubers of Urikawa were planted. After that, the water depth was kept at 3 to 4 cm, and when the Nobie and Firefly reached the 0.5 leaf stage and Urikawa reached the primary leaf stage, the compound of the present invention was diluted with water to prepare a wettable powder according to a conventional formulation method. The liquid was uniformly dropped with a pipette so that the predetermined amount of active ingredient was obtained. On the 14th day after the chemical treatment, the growth condition of the plant was visually observed, and the herbicidal effect was evaluated by the weeding rate (%) of 0 (equivalent to the untreated group) to 100 (complete killing), and the results in Table 16 are shown. Obtained.

[0180]

[Table 86]

Test Example 3 Upland soil was filled in a 1 / 150,000 hectare pot and seeds of various plants were sown. After that, the plant has a certain leaf age ((1) Nobie 1.6-2.5 leaf stage, (2) Mejisuba 1.5-2.5 leaf stage, (3) Aubiyu 0.2-1.5 leaf stage. , (4) Sida 0.1 to 1.2 leaf stage, (5)
Malva morning glory 0.2-2.0 leaf stage, (6) Ona fir 0.
2 to 2.1 leaf stage, (7) rice 1.5 to 2.2 leaf stage, (8) wheat 2.0 to 3.3 leaf stage, (9) corn 2.2.
3.4 leaf stage, (10) soybean primary leaf to 0.2 leaf stage), when the wettable powder prepared by the compound of the present invention according to the usual formulation method is weighed so as to have a predetermined active ingredient amount And diluted to 500 liters of water per hectare. Further, 0.1% by volume of agricultural spreading agent was added to the diluted solution, and the leaves were treated with a small spray. From 17 to 23 days after the chemical treatment, the growth state of various plants is visually observed and 0 (equivalent to the untreated group) to
The herbicidal effect was evaluated based on the weeding rate (%) of 100 (complete withering), and the results shown in Table 17 were obtained.

[0182]

[Table 87]

[0183]

[Table 88]

[0184]

[Table 89]

Next, formulation examples of the present invention will be described. Formulation Example 1 (1) Compound No. 11 ... 75 parts by weight (2) Gelopon T-77 ... 14.5 parts by weight (trade name; manufactured by Rhone-Poulin) (3) NaCl ... 10 parts by weight (4) Dextrin ... 0.5 parts by weight Put in a high-speed mixing granulator, and then there 2
Granule wettable powder is obtained by adding 0% water and granulating and drying.

Formulation Example 2 (1) Kaolin: 78 parts by weight (2) Laberin FAN: 2 parts by weight (trade name; manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd.) (3) Solpol 5039: 5 parts by weight (trade name: Toho) Chemical Industry Co., Ltd. (4) Carplex ... 15 parts by weight (trade name; manufactured by Shionogi Pharmaceutical Co., Ltd.) The mixture of the components (1) to (4) and the compound No. 21
The wettable powder is obtained by mixing and at a weight ratio of 9: 1.

Formulation Example 3 (1) High Filler No. 10 ... 33 parts by weight (trade name; manufactured by Matsumura Sangyo Co., Ltd.) (2) Solpol 5050 ... 3 parts by weight (product name; manufactured by Toho Chemical Industry Co., Ltd.) (3) Solpol 5073 ... 4 parts by weight (product name; (Toho Chemical Industry Co., Ltd.) (4) Compound No. 61 ... 60 parts by weight The above-mentioned respective components (1) to (4) are mixed to obtain a wettable powder.

Formulation Example 4 (1) Compound No. 1 ... 4 parts by weight (2) Corn oil ... 79 parts by weight (3) Solpol 3815K ... 15 parts by weight (trade name; manufactured by Toho Chemical Industry Co., Ltd.) (4) Organic bentonite ... 2 parts by weight (trade name; New Dio) Reuben; manufactured by Shiraishi Industry Co., Ltd. The above components (1) to (4) are uniformly mixed, and a wet pulverizer (Dyno Mill: Willy A. Bachofen) is mixed.
(Manufactured by the company) to obtain a suspension composition.

Formulation Example 5 (1) Compound No. 203 4 parts by weight (2) Bentonite 30 parts by weight (3) Calcium carbonate 61.5 parts by weight (4) Toxanone GR-31A 3 parts by weight (trade name; Sanyo Chemical Industries, Ltd.) (5) Lignin sulfonic acid calcium salt ... 1.5 parts by weight Preliminarily ground (1), (2) and (3) are mixed,
(4), (5) and water are added thereto and mixed, and extrusion granulated. Then, it is dried and sized to obtain granules.

Formulation Example 6 (1) Compound No. 350 ... 30 parts by weight (2) Sikhlite ... 60 parts by weight (trade name; manufactured by Sieglite Co., Ltd.) (3) Newkalgen WG-1 ... 5 parts by weight (trade name; manufactured by Takemoto Yushi Co., Ltd.) (4) ) New Kalgen FS-7 ... 5 parts by weight (trade name; manufactured by Takemoto Yushi Co., Ltd.) (1), (2) and (3) are mixed and passed through a pulverizer, and then (4) is added and kneaded. After that, extrusion granulation is performed. afterwards,
The wettable powder is obtained by drying and sizing.

Production Example 7 (1) Compound No. 1 ... 28 parts by weight (2) Sopropol FL ... 2 parts by weight (trade name; manufactured by Rhone-Poulin) (3) Solpol 355 ... 1 part by weight (product name; manufactured by Toho Chemical Industry Co., Ltd.) (4) IP Solvent 1620 ... 32 parts by weight (trade name; manufactured by Idemitsu Petrochemical Co., Ltd.) (5) Ethylene glycol ... 6 parts by weight (6) Water ... 31 parts by weight The above components (1) to (6) are mixed and wet. An aqueous suspension is obtained by pulverizing with a pulverizer (Dyno Mill).

Formulation Example 8 (1) Compound No. 506 ... 75 parts by weight (2) Gelopon T-77 ... 14.5 parts by weight (trade name; manufactured by Rhone-Poulin) (3) NaCl ... 10 parts by weight (4) Dextrin ... 0.5 parts by weight Put in a high-speed mixing granulator, and then there 2
Granule wettable powder is obtained by adding 0% water and granulating and drying.

Formulation Example 9 (1) Kaolin: 78 parts by weight (2) Laberin FAN: 2 parts by weight (trade name; manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd.) (3) Solpol 5039: 5 parts by weight (trade name: Toho) Chemical Industry Co., Ltd. (4) Carplex ... 15 parts by weight (trade name; manufactured by Shionogi Pharmaceutical Co., Ltd.) The mixture of the components (1) to (4) and the compound No. 52
The wettable powder is obtained by mixing 1 and 9 in a weight ratio of 9: 1.

 ─────────────────────────────────────────────────── ─── Continuation of front page (72) Hiroshi Sasaki 2-3-1, Nishi-Shibukawa, Kusatsu City, Shiga Prefecture Central Research Laboratory, Ishihara Sangyo Co., Ltd. (72) Koji Kikukawa 2-3-3 Nishi-Shibukawa, Kusatsu City, Shiga Prefecture 1 Ishihara Sangyo Co., Ltd. Central Research Institute (72) Inventor Soichiro Nagayama 2-3-1 Nishishibukawa, Kusatsu City, Shiga Prefecture Ishihara Sangyo Co., Ltd. Central Research Laboratory (72) Inventor Makiko Mitani 2-chome Nishishibukawa, Kusatsu City, Shiga Prefecture No. 3-1 Ishihara Sangyo Co., Ltd. Central Research Laboratory

Claims (16)

[Claims] 1. A compound represented by the general formula (I): Embedded image And R ₁ is a hydrogen atom, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted alkoxy group, an optionally substituted alkylthio group, An optionally substituted alkylcarbonyl group, an optionally substituted alkoxycarbonyl group, an optionally substituted alkylsulfinyl group, an optionally substituted alkylsulfonyl group, And G is a halogen atom, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted alkoxy group, an optionally substituted alkylthio group, a substituted Optionally substituted alkylcarbonyl group, optionally substituted alkoxycarbonyl group, optionally substituted alkylsulfinyl group, optionally substituted alkylsulfonyl group, And R ₂ and R ₃ are each independently a hydrogen atom, an alkyl group, an alkylcarbonyl group, an alkylsulfinyl group or an alkylsulfonyl group, and R ₄ , R ₅ and R
₈ are each independently a hydrogen atom or an alkyl group, R ₆
And R ₇ are each independently a hydrogen atom, an alkyl group, an alkylcarbonyl group or an alkoxycarbonyl group, and n
Is an integer of 0 to 3, X and Y are each independently a halogen atom, an alkyl group, a haloalkyl group, an alkoxyalkyl group, an alkoxy group, a haloalkoxy group, a monoalkylamino group or a dialkylamino group, and A is CH or N), and a pyridonesulfonylurea compound or a salt thereof. 2. Q is The compound or its salt according to claim 1, which is a group. 3. Q is The compound or its salt according to claim 1, which is a group. 4. R ₁ is a hydrogen atom, an alkyl group which may be substituted, an alkenyl group which may be substituted, an alkynyl group which may be substituted, an alkoxy group which may be substituted, an alkoxycarbonyl which may be substituted. A group, an optionally substituted alkylsulfonyl group, or And G is a halogen atom, an optionally substituted alkyl group, an optionally substituted alkoxy group, an optionally substituted alkylthio group, A group, R ₂ and R ₃ are each independently a hydrogen atom or an alkyl group, R ₄ and R ₅ are each independently an alkyl group, R ₈ is a hydrogen atom, and n is 0 to 3 X is a halogen atom, an alkyl group, an alkoxy group or a haloalkoxy group, and A is C.
The compound according to claim 1, 2 or 3 which is H or N, or a salt thereof. 5. R ₁ is a hydrogen atom, an optionally substituted alkyl group, an alkenyl group, an alkynyl group, an alkoxy group,
Alkoxycarbonyl group, alkylsulfonyl group or And G is a halogen atom, an optionally substituted alkyl group, an optionally substituted alkoxy group, an alkylthio group, A group, R ₂ and R ₃ are each independently a hydrogen atom or an alkyl group, R ₄ and R ₅ are each independently an alkyl group, R ₈ is a hydrogen atom, and n is 0 or 1 Wherein X and Y are each independently a halogen atom, an alkyl group or an alkoxy group, and A is CH or N. 4. The compound or a salt thereof according to claim 1, 2 or 3. 6. R ₁ is selected from the group consisting of hydrogen atom, halogen atom, alkyl group, alkoxy group, alkylthio group, alkylcarbonyl group, alkoxycarbonyl group, alkylsulfinyl group, alkylsulfonyl group, phenyl group and benzyloxy group. An alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an alkoxycarbonyl group, an alkylsulfonyl group which may be substituted with at least one substituent And G is a halogen atom, an alkyl group which may be substituted with a halogen atom, an alkoxy group which may be substituted with a halogen atom, an alkylthio group, A group, R ₂ and R ₃ are each independently a hydrogen atom or an alkyl group, R ₄ and R ₅ are each independently an alkyl group, R ₈ is a hydrogen atom, and n is 0 or 1 Wherein X and Y are each independently a halogen atom, an alkyl group or an alkoxy group, and A is CH or N. 4. The compound or a salt thereof according to claim 1, 2 or 3. 7. A compound represented by the general formula (I): Embedded image And R ₁ is a hydrogen atom, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted alkoxy group, an optionally substituted alkylthio group, An optionally substituted alkylcarbonyl group, an optionally substituted alkoxycarbonyl group, an optionally substituted alkylsulfinyl group, an optionally substituted alkylsulfonyl group, And G is a halogen atom, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted alkoxy group, an optionally substituted alkylthio group, a substituted Optionally substituted alkylcarbonyl group, optionally substituted alkoxycarbonyl group, optionally substituted alkylsulfinyl group, optionally substituted alkylsulfonyl group, And R ₂ and R ₃ are each independently a hydrogen atom, an alkyl group, an alkylcarbonyl group, an alkylsulfinyl group or an alkylsulfonyl group, and R ₄ , R ₅ and R
₈ are each independently a hydrogen atom or an alkyl group, R ₆
And R ₇ are each independently a hydrogen atom, an alkyl group, an alkylcarbonyl group or an alkoxycarbonyl group, and n
Is an integer of 0 to 3, X and Y are each independently a halogen atom, an alkyl group, a haloalkyl group, an alkoxyalkyl group, an alkoxy group, a haloalkoxy group, a monoalkylamino group or a dialkylamino group, and A is CH or N) and a pyridonesulfonylurea compound or a salt thereof as an active ingredient. 8. Q is The herbicide according to claim 7, which is a base. 9. Q is The herbicide according to claim 7, which is a base. 10. R ₁ is a hydrogen atom, an alkyl group which may be substituted, an alkenyl group which may be substituted, an alkynyl group which may be substituted, an alkoxy group which may be substituted,
An optionally substituted alkoxycarbonyl group, an optionally substituted alkylsulfonyl group or And G is a halogen atom, an optionally substituted alkyl group, an optionally substituted alkoxy group, an optionally substituted alkylthio group, A group, R ₂ and R ₃ are each independently a hydrogen atom or an alkyl group, R ₄ and R ₅ are each independently an alkyl group, R ₈ is a hydrogen atom, and n is 0 to 3 X is a halogen atom, an alkyl group, an alkoxy group or a haloalkoxy group, and A is C.
The herbicide according to claim 7, 8 or 9, which is H or N. 11. R ₁ is a hydrogen atom, an optionally substituted alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an alkoxycarbonyl group, an alkylsulfonyl group, or And G is a halogen atom, an optionally substituted alkyl group, an optionally substituted alkoxy group, an alkylthio group, A group, R ₂ and R ₃ are each independently a hydrogen atom or an alkyl group, R ₄ and R ₅ are each independently an alkyl group, R ₈ is a hydrogen atom, and n is 0 or 1 Wherein X and Y are each independently a halogen atom, an alkyl group or an alkoxy group, and A is CH or N. 10. 12. R ₁ is selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an alkylthio group, an alkylcarbonyl group, an alkoxycarbonyl group, an alkylsulfinyl group, an alkylsulfonyl group, a phenyl group and a benzyloxy group. An alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an alkoxycarbonyl group, an alkylsulfonyl group which may be substituted with at least one substituent And G is a halogen atom, an alkyl group which may be substituted with a halogen atom, an alkoxy group which may be substituted with a halogen atom, an alkylthio group, A group, R ₂ and R ₃ are each independently a hydrogen atom or an alkyl group, R ₄ and R ₅ are each independently an alkyl group, R ₈ is a hydrogen atom, and n is 0 or 1 Wherein X and Y are each independently a halogen atom, an alkyl group or an alkoxy group, and A is CH or N. 10. 13. A compound represented by the general formula (I): [Chemical formula 26] And R ₁ is a hydrogen atom, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted alkoxy group, an optionally substituted alkylthio group, An optionally substituted alkylcarbonyl group, an optionally substituted alkoxycarbonyl group, an optionally substituted alkylsulfinyl group, an optionally substituted alkylsulfonyl group, And G is a halogen atom, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted alkoxy group, an optionally substituted alkylthio group, a substituted An optionally substituted alkylcarbonyl group, an optionally substituted alkoxycarbonyl group, an optionally substituted alkylsulfinyl group, an optionally substituted alkylsulfonyl group, And R ₂ and R ₃ are each independently a hydrogen atom, an alkyl group, an alkylcarbonyl group, an alkylsulfinyl group or an alkylsulfonyl group, and R ₄ , R ₅ and R
₈ are each independently a hydrogen atom or an alkyl group, R ₆
And R ₇ are each independently a hydrogen atom, an alkyl group, an alkylcarbonyl group or an alkoxycarbonyl group, and n
Is an integer of 0 to 3, X and Y are each independently a halogen atom, an alkyl group, a haloalkyl group, an alkoxyalkyl group, an alkoxy group, a haloalkoxy group, a monoalkylamino group or a dialkylamino group, and A is CH or N), which is a pyridonesulfonylurea compound or a salt thereof, and an amount of the herbicidal active ingredient is applied to the harmful weed control method. 14. A compound represented by the general formula (I): Embedded image And R ₁ is a hydrogen atom, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted alkoxy group, an optionally substituted alkylthio group, An optionally substituted alkylcarbonyl group, an optionally substituted alkoxycarbonyl group, an optionally substituted alkylsulfinyl group, an optionally substituted alkylsulfonyl group, And G is a halogen atom, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted alkoxy group, an optionally substituted alkylthio group, a substituted Optionally substituted alkylcarbonyl group, optionally substituted alkoxycarbonyl group, optionally substituted alkylsulfinyl group, optionally substituted alkylsulfonyl group, And R ₂ and R ₃ are each independently a hydrogen atom, an alkyl group, an alkylcarbonyl group, an alkylsulfinyl group or an alkylsulfonyl group, and R ₄ , R ₅ and R
₈ are each independently a hydrogen atom or an alkyl group, R ₆
And R ₇ are each independently a hydrogen atom, an alkyl group, an alkylcarbonyl group or an alkoxycarbonyl group, and n
Is an integer of 0 to 3, X and Y are each independently a halogen atom, an alkyl group, a haloalkyl group, an alkoxyalkyl group, an alkoxy group, a haloalkoxy group, a monoalkylamino group or a dialkylamino group, and A is CH or N) and a pyridonesulfonylurea compound or a salt thereof, and at least one active ingredient compound of another herbicide. 15. A compound represented by the general formula (I): Embedded image And R ₁ is a hydrogen atom, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted alkoxy group, an optionally substituted alkylthio group, An optionally substituted alkylcarbonyl group, an optionally substituted alkoxycarbonyl group, an optionally substituted alkylsulfinyl group, an optionally substituted alkylsulfonyl group, And G is a halogen atom, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted alkoxy group, an optionally substituted alkylthio group, a substituted Optionally substituted alkylcarbonyl group, optionally substituted alkoxycarbonyl group, optionally substituted alkylsulfinyl group, optionally substituted alkylsulfonyl group, And R ₂ and R ₃ are each independently a hydrogen atom, an alkyl group, an alkylcarbonyl group, an alkylsulfinyl group or an alkylsulfonyl group, and R ₄ , R ₅ and R
₈ are each independently a hydrogen atom or an alkyl group, R ₆
And R ₇ are each independently a hydrogen atom, an alkyl group, an alkylcarbonyl group or an alkoxycarbonyl group, and n
Is an integer of 0 to 3, X and Y are each independently a halogen atom, an alkyl group, a haloalkyl group, an alkoxyalkyl group, an alkoxy group, a haloalkoxy group, a monoalkylamino group or a dialkylamino group, and A is CH is N or N) and a pyridonesulfonylurea compound represented by the general formula (I
I); (In the formula, Q is as described above, Z ₁ is —NH ₂ group,
An NCO group or —NHCO ₂ R ₉ group, and R ₉ is an alkyl group or an aryl group), and a pyridone compound represented by the general formula (III); (In the formula, X, Y and A are as described above, and Z ₂ is Z ₁
Is a —NH ₂ group, it is a —N (R ₈ ) CO ₂ R ₉ group or a —NCO group, and Z ₁ is a —NCO group or a —NHCO ₂ group.
R ₉ group is a —NHR ₈ group, and R ₈ and R ₉ are the same as those described above), and then a salt forming reaction is carried out if desired. A method for producing a pyridonesulfonylurea compound represented by the general formula (I) or a salt thereof. 16. A compound represented by the general formula (II-1):[Chemical 40]And R is₁Is a hydrogen atom, optionally substituted alkyl
Group, optionally substituted alkenyl group, optionally substituted
Alkynyl group, optionally substituted alkoxy group, substituted
Optionally substituted alkylthio group, optionally substituted alkyl
Carbonyl group, optionally substituted alkoxycarbonyl
Group, optionally substituted alkylsulfinyl group, substituted
An optionally substituted alkylsulfonyl group,Is a group, G is a halogen atom, optionally substituted alkyl
Group, optionally substituted alkenyl group, optionally substituted
Alkynyl group, optionally substituted alkoxy group, substituted
Optionally substituted alkylthio group, optionally substituted alkyl
Carbonyl group, optionally substituted alkoxycarbonyl group
Group, optionally substituted alkylsulfinyl group, substituted
An alkylsulfonyl group which may beAnd R is₂And R₃Are each independently a hydrogen atom,
Kill group, alkylcarbonyl group, alkylsulfinyl
A group or an alkylsulfonyl group, R_FourAnd R _FiveIs each
Each independently a hydrogen atom or an alkyl group, R₆And R
₇Are each independently a hydrogen atom, alkyl group,
A carbonyl group or an alkoxycarbonyl group, and n is 0 to
Which is an integer of 3).