JP2017025060A - Heterocyclic amide compound - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide novel agrochemicals, particularly herbicides.SOLUTION: The present invention provides heterocyclic amide compounds represented by the following formula [Ris a substituent comprising a tertiary amino group and a group comprising sulfone, carboxyl or carbonyl].SELECTED DRAWING: None

Description

  The present invention relates to a novel heterocyclic amide compound and a salt thereof, and an agrochemical, particularly a herbicide, containing the heterocyclic amide compound and a salt thereof as an active ingredient. The agrochemical in the present invention means an insecticide / acaricide, nematicide, herbicide, fungicide, etc. in the field of agriculture and horticulture.

  For example, Patent Documents 1 to 8 disclose certain types of heterocyclic amide compounds, but do not disclose any heterocyclic amide compounds according to the present invention.

International Publication No. 2013/092834 International Publication No. 2013/144231 International Publication No. 2013/164333 International Publication No. 2014/086737 International Publication No. 2014/192936 International Publication No. 2015/007633 International Publication No. 2016/016107 International Publication No. 2016/038173

  The object of the present invention is a highly safe and effective herbicide active ingredient that reliably shows effects on various weeds at a lower dose, and has reduced problems such as soil contamination and effects on subsequent crops. It is to provide useful chemical substances.

  As a result of intensive studies aimed at solving the above-mentioned problems, the present inventors have found that the novel heterocyclic amide compound represented by the following formula (1) according to the present invention has excellent herbicidal activity and target as a herbicide. The present invention has been completed by discovering that it is a highly useful compound that has a high safety against certain crops and has almost no adverse effect on non-target organisms such as mammals, fish and beneficial insects.

  That is, the present invention relates to the following [1] to [4].

    [1]

[Wherein Q represents an aromatic heterocycle represented by any one of Q-1 to Q-7,

  W represents an aromatic heterocyclic ring represented by W-1,

X represents an oxygen atom or a sulfur atom,
R ^1a represents (C ₁ -C ₆ ) alkyl, —S (O) _m1 R ¹⁴ , V-1, V-2, V-3, V-4 or V-5, optionally substituted with R ⁶ . Represent,
V-1 to V-5 each represent a substituent represented by the following structure,

R ^2a represents a halogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, —C (O) R ²⁵ , cyano, nitro, —OR ²⁶ or —S (O) _m5 R ²⁷ , and n is When each represents an integer of 2 or more, each R ^2a may be the same as or different from each other;
Further, when two R ^2a are adjacent, the two adjacent R ^2a are —CH ₂ CH ₂ CH ₂ —, —CH ₂ CH ₂ O—, —CH ₂ OCH ₂ —, —OCH ₂ O—, _{-CH 2 CH 2 S -, -} CH 2 SCH 2 -, - CH 2 CH 2 CH 2 CH 2 -, - CH 2 CH 2 CH 2 O -, - CH 2 CH 2 OCH 2 -, - CH 2 OCH 2 Each of the two R ^2a is formed by forming O—, —OCH ₂ CH ₂ O—, —CH ₂ CH ₂ CH ₂ S—, —OCH ₂ CH ₂ S— or —CH═CH—CH═CH—. A 5-membered ring or a 6-membered ring may be formed together with the carbon atom to which is bonded, and at this time, the hydrogen atom bonded to each carbon atom forming the ring is a halogen atom, a C ₁ -C ₆ alkyl group or C _1. arbitrarily by ~C ₆ haloalkyl group It may have been conversion,
R ³ is a hydrogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₃ -C ₆ cycloalkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl or -C (O) R ²⁹ Represents
R ^4a , R ^4b , R ^4c , R ^4d , R ^4e , R ^4f , R ^4g and R ^4h are each independently optionally substituted with a hydrogen atom, a halogen atom, C ₁ -C ₆ alkyl, or R ³¹ . _(C 1 _{~C 6)} represents _alkyl, C 3 -C ₆ cycloalkyl, phenyl substituted by phenyl or ^(R _{32) q2,}
R ^5a , R ^5b and R ^5c are each independently substituted with a hydrogen atom, C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl, phenyl or (R ³² ) _q2 optionally substituted with R ³¹ Represented phenyl,
R ^{6 _{is, -N (R 7) R 8}} , -S (O) 2 N (R 7) R 8, U-1, U-2, U-3, U-4, U-5, U-6 Or U-7,
U-1 to U-7 each represent a heterocyclic ring or a substituent represented by the following structure,

R ⁷ represents —C (O) R ¹⁰ , —C (S) R ¹⁰ or —S (O) ₂ R ¹⁰ ,
R ⁸ is a hydrogen atom, C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl optionally substituted by R ¹⁵ , C ₃ -C ₆ cycloalkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ represents alkynyl, phenyl or —OR ¹⁷
R ⁹ represents a halogen atom, C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl, and when p 4, p 6 or p 8 represents an integer of 2 or more, each R ⁹ may be the same or mutually They may be different,
R ¹⁰ is a hydrogen atom, C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl optionally substituted by R ¹⁹ , C ₃ -C ₆ cycloalkyl, C ₂ -C ₆ alkenyl, C ₂ -C _{6 represents} alkynyl, —OR ¹¹ or —N (R ¹² ) R ¹³ ;
R ¹¹ represents a hydrogen atom, C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl,
R ¹² and R ¹³ each independently represent a hydrogen atom, C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl, or R ¹² together with R ¹³ is a C ₂ -C ₆ alkylene chain. Represents that a 3- to 7-membered ring may be formed together with the nitrogen atom to which R ¹² and R ¹³ are bonded, and this alkylene chain contains one oxygen atom, sulfur atom or nitrogen atom. But often, and halogen _atom, C 1 -C ₆ alkyl _group, C 1 -C ₆ haloalkyl _group, C 1 -C ₆ alkoxy group, a formyl _group, C 1 -C ₆ alkylcarbonyl _group, C 1 -C ₆ alkoxycarbonyl Optionally substituted by a group, an oxo group or a thioxo group,
R ¹⁴ represents (C ₁ -C ₆ ) alkyl optionally substituted with R ⁶ ;
R ¹⁵ represents a halogen atom, cyano or —OR ¹⁶ ,
R ¹⁶ and R ¹⁷ each independently represent a hydrogen atom, C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl,
R ¹⁸ represents C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl,
R ¹⁹ represents a halogen atom or —S (O) _m2 R ²⁰ ,
R ²⁰ , R ²¹ and R ²² each independently represent C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl,
R ²⁵ represents a hydrogen _atom, C 1 -C _{6 alkyl,} C 1 -C ₆ haloalkyl or ^{-OR 28,}
R ²⁶ represents a hydrogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl or phenyl;
R ²⁷ represents C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl,
R ²⁸ represents a hydrogen atom, C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl,
R ²⁹ represents a hydrogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl or —OR ³⁰ ;
R ³⁰ represents a hydrogen atom, C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl,
R ³¹ represents a halogen atom, phenyl, —OR ³³ or —S (O) _m6 R ³⁴ ,
R ³² represents a halogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl or —OR ^35, and when q 2 represents an integer of 2 or more, each R ³² may be the same as each other or They may be different,
Furthermore, when two R ³² are adjacent, two adjacent R ³² are —CH ₂ CH ₂ CH ₂ —, —CH ₂ CH ₂ O—, —CH ₂ OCH ₂ —, —OCH ₂ O—, _{-CH 2 CH 2 S -, -} CH 2 SCH 2 -, - CH 2 CH 2 CH 2 CH 2 -, - CH 2 CH 2 CH 2 O -, - CH 2 CH 2 OCH 2 -, - CH 2 OCH 2 _{O -, - OCH 2 CH 2} O -, - CH 2 CH 2 CH 2 S -, - OCH by 2 _CH 2 S- or forming a -CH = CH-CH = CH-, each of the two ^{R 32} A 5-membered ring or a 6-membered ring may be formed together with the carbon atom to which is bonded, and at this time, the hydrogen atom bonded to each carbon atom forming the ring is a halogen atom, a C ₁ -C ₆ alkyl group or C _1. arbitrarily by ~C ₆ haloalkyl group It may have been conversion,
R ³³ represents a hydrogen atom, C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl,
R ³⁴ represents C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl,
R ³⁵ represents a hydrogen atom, C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl,
m1, m5 and m6 each independently represents an integer of 0, 1 or 2;
n independently represents an integer of 0, 1, 2, or 3,
p4 represents an integer of 0, 1, 2, 3 or 4;
p6 represents an integer of 0, 1, 2, 3, 4, 5 or 6,
p8 represents an integer of 0, 1, 2, 3, 4, 5, 6, 7 or 8;
q2 represents an integer of 1, 2, 3, 4 or 5. Or a salt thereof.

[2]
Q represents Q-1 or Q-3,
X represents an oxygen atom,
R ^1a represents (C ₁ -C ₆ ) alkyl, —S (O) _m1 R ¹⁴ or V-1, optionally substituted with R ⁶ ,
R ^2a represents C ₁ -C ₆ haloalkyl,
R ³ represents a hydrogen atom,
R ^4a represents a hydrogen atom or C ₁ -C ₆ alkyl;
R ^5a represents C ₁ -C ₆ alkyl;
R ⁶ represents —N (R ⁷ ) R ⁸ , U-1, U-3, U-4, U-6 or U-7,
R ⁸ is a hydrogen atom, C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl, C ₃ -C ₆ cycloalkyl, C ₂ -C ₆ alkynyl, phenyl or —OR optionally substituted by R ¹⁵ . ¹⁷
R ¹⁰ represents C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl, C ₃ -C ₆ cycloalkyl, —OR ¹¹ or —N ¹¹ or —N (R ¹² ) R ¹³ optionally substituted by R ¹⁹ . ,
R ¹¹ represents C ₁ -C ₆ alkyl,
R ¹² and R ¹³ each independently represent a hydrogen atom or C ₁ -C ₆ alkyl;
R ¹⁶ , R ¹⁷ , R ¹⁸ , R ²⁰ , R ²¹ and R ²² each independently represent C ₁ -C ₆ alkyl;
m1 represents an integer of 0;
n represents an integer of 1;
p4, p6, and p8 represent an integer of 0. ] The heterocyclic amide compound or its salt as described in said [1] represented by these.

[3]
An agrochemical containing as an active ingredient one or more selected from the heterocyclic amide compounds according to the above [1] to [2] and salts thereof.

[4]
A herbicide containing, as an active ingredient, one or more selected from the heterocyclic amide compounds according to the above [1] to [2] and salts thereof.

  The compound of the present invention has excellent herbicidal activity against various weeds and has high safety against the target crop. Furthermore, it has little adverse effect on non-target organisms such as mammals, fish and beneficial insects, has low persistence, and has a light impact on the environment.

  Therefore, the present invention can provide a herbicide useful in the field of agriculture and horticulture such as paddy fields, upland fields, and orchards.

  The compounds included in the present invention may have geometrical isomers of E-form and Z-form depending on the type of substituent, and the present invention is not limited to these E-form, Z-form or E-form. And a mixture containing the Z-form in an arbitrary ratio. In addition, the compounds included in the present invention include optically active substances resulting from the presence of one or more asymmetric carbon atoms, but the present invention includes all optically active substances or racemates.

  Among the compounds included in the present invention, those that can be converted into acid addition salts according to a conventional method include, for example, hydrohalic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid, hydroiodic acid, and the like. Salt of inorganic acid such as salt, nitric acid, sulfuric acid, phosphoric acid, chloric acid, perchloric acid, salt of sulfonic acid such as methanesulfonic acid, ethanesulfonic acid, trifluoromethanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, Salts of carboxylic acids such as formic acid, acetic acid, propionic acid, trifluoroacetic acid, fumaric acid, tartaric acid, succinic acid, maleic acid, malic acid, succinic acid, benzoic acid, mandelic acid, ascorbic acid, lactic acid, gluconic acid, citric acid, etc. A salt of an amino acid such as glutamic acid or aspartic acid can be used.

  Alternatively, among the compounds included in the present invention, those that can be converted into a metal salt according to a conventional method include, for example, alkali metal salts such as lithium, sodium, and potassium, and alkaline earth metals such as calcium, barium, and magnesium. It can be a salt or a salt of aluminum.

  Next, specific examples of each substituent shown in the present specification are shown below. Here, n- represents normal, i- represents iso, s- represents secondary, and tert- represents tertiary, and Ph represents phenyl.

  Examples of the halogen atom in the present specification include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom. In the present specification, the notation “halo” also represents these halogen atoms.

The notation of C _a -C _b alkyl in the present specification represents a linear or branched hydrocarbon group having a carbon number of _a to _b , for example, methyl group, ethyl group, n-propyl group, Specific examples include i-propyl group, n-butyl group, i-butyl group, s-butyl group, tert-butyl group, n-pentyl group, 1,1-dimethylpropyl group, n-hexyl group, and the like. Each selected range of carbon atoms is selected.

In the present specification, C _a -C _b cycloalkyl represents a cyclic hydrocarbon group having a carbon number of _a to _b , and forms a monocyclic or complex ring structure having 3 to 6 members. I can do it. Each ring may be optionally substituted with an alkyl group within the range of the specified number of carbon atoms. Specific examples include cyclopropyl group, 1-methylcyclopropyl group, 2-methylcyclopropyl group, 2,2-dimethylcyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, etc. Selected in a range of numbers.

In the present specification, C _a -C _b alkenyl is a linear or branched chain composed of _a to _b carbon atoms and has one or more double bonds in the molecule. Represents a saturated hydrocarbon group, for example, vinyl group, 1-propenyl group, 2-propenyl group, 1-methylethenyl group, 2-butenyl group, 2-methyl-2-propenyl group, 3-methyl-2-butenyl group, 1 , 1-dimethyl-2-propenyl group and the like are listed as specific examples, and each is selected within the range of the designated number of carbon atoms.

In the present specification, C _a -C _b alkynyl is a linear or branched chain composed of _a to _b carbon atoms and has one or more triple bonds in the molecule. Represents a hydrocarbon group, for example, ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1,1-dimethyl-2-propynyl group, etc. Each of which is selected for each specified number of carbon atoms.

In the present specification, C _a -C _b haloalkyl is represented by a linear or branched chain having _a to _b carbon atoms in which a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom. Represents a hydrocarbon group, and when substituted by two or more halogen atoms, the halogen atoms may be the same as or different from each other. For example, fluoromethyl group, chloromethyl group, bromomethyl group, iodomethyl group, difluoromethyl group, dichloromethyl group, trifluoromethyl group, chlorodifluoromethyl group, trichloromethyl group, bromodifluoromethyl group, 2-fluoroethyl group, 2- Chloroethyl group, 2-bromoethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group, 2-chloro-2,2-difluoroethyl group, 2,2,2-trichloroethyl group, 1 , 1,2,2-tetrafluoroethyl group, 2-chloro-1,1,2-trifluoroethyl group, pentafluoroethyl group, 3,3,3-trifluoropropyl group, 2,2,3,3 , 3-pentafluoropropyl group, 1,1,2,3,3,3-hexafluoropropyl group, heptafluoropropyl group 2,2,2-trifluoro-1- (trifluoromethyl) ethyl group, 1,2,2,2-tetrafluoro-1- (trifluoromethyl) ethyl group, 2,2,3,3,4, Specific examples include 4,4-heptafluorobutyl group, nonafluorobutyl group and the like, and each is selected within the range of the number of carbon atoms designated.

The notation of C _a -C _b alkoxy in the present specification represents an alkyl-O— group having the above-mentioned meaning consisting of _a to _b carbon atoms. Specific examples include an i-propyloxy group, an n-butyloxy group, an i-butyloxy group, an s-butyloxy group, a tert-butyloxy group, and the like, and each is selected within the range of the designated number of carbon atoms.

The notation of C _a -C _b alkylcarbonyl in the present specification represents an alkyl-C (O) -group having the above-mentioned meaning consisting of _a to _b carbon atoms, for example, acetyl group, propionyl group, butyryl group. , Isobutyryl group, valeryl group, isovaleryl group, 2-methylbutanoyl group, pivaloyl group, hexanoyl group, heptanoyl group, and the like, and specific examples thereof are selected within the range of the number of carbon atoms designated.

The notation of C _a -C _b alkoxycarbonyl in the present specification represents an alkyl-O—C (O) — group having the above-mentioned meaning consisting of _a to _b carbon atoms, for example, methoxycarbonyl group, ethoxycarbonyl Group, n-propyloxycarbonyl group, i-propyloxycarbonyl group, n-butoxycarbonyl group, i-butoxycarbonyl group, tert-butoxycarbonyl group and the like, and specific ranges of the number of carbon atoms are designated. Selected.

Notation such as _(C a ~C _b) alkyl optionally substituted by R ⁶ in the present specification, by any R ^6, carbon atoms in which a hydrogen atom bonded to carbon atom is optionally substituted a~ It represents an alkyl group as defined above consisting of b, and is selected in the range of the respective designated number of carbon atoms. At this time, when two or more substituents R ⁶ on each (C _a -C _b ) alkyl group are present, each R ⁶ may be the same as or different from each other.

In the present specification, “R ¹² may form a C ₂ -C ₆ alkylene chain together with R ¹³ to form a 3- to 7-membered ring together with the nitrogen atom to which R ¹² and R ¹³ are bonded. indicates that, at this time the alkylene chain an oxygen atom, may contain one sulfur atom or a nitrogen atom, and a halogen _atom, C 1 -C ₆ alkyl _group, C 1 -C ₆ haloalkyl _group, C 1 -C ₆ Specific examples of the notation such as “optionally substituted by an alkoxy group, a formyl group, a C ₁ -C ₆ alkylcarbonyl group, a C ₁ -C ₆ alkoxycarbonyl group, an oxo group or a thioxo group” , Azetidine, azetidin-2-one, pyrrolidine, pyrrolidin-2-one, oxazolidine, oxazolidine-2-one, oxazolidine-2-thione, Thiazolidine, thiazolidine-2-one, thiazolidine-2-thione, imidazolidine, imidazolidine-2-one, imidazolidine-2-thione, piperidine, piperidin-2-one, piperidine-2-thione, 2H-3,4 , 5,6-tetrahydro-1,3-oxazin-2-one, 2H-3,4,5,6-tetrahydro-1,3-oxazin-2-thione, morpholine, 2H-3,4,5,6 -Tetrahydro-1,3-thiazin-2-one, 2H-3,4,5,6-tetrahydro-1,3-thiazin-2-thione, thiomorpholine, thiomorpholine-1-oxide, thiomorpholine-1, 1-dioxide, perhydropyrimidin-2-one, piperazine, homopiperidine, homopiperidin-2-one, heptamethyleneimine, etc. It is selected from the range number of each of the specified atoms.

Next, the manufacturing method of this invention compound is demonstrated below.
Manufacturing method A
The heterocyclic amide compound represented by the formula (1) can be produced, for example, by reacting the compound represented by the formula (2) with the compound represented by the formula (3a).

Formula (2) [wherein Q and R ³ represent the same meaning as described above. Or a salt thereof and formula (3a) wherein W and X are as defined above. Or a salt thereof in a solvent or without solvent, using a base if necessary, a condensing agent if necessary, a catalyst if necessary, and adding an additive if necessary By reacting, formula (1) [wherein Q, R ³ , W and X have the same meaning as described above. This invention compound represented by this can be manufactured.

  In this reaction, the compound represented by the formula (3a) can be used in the range of 0.1 to 100 equivalents with respect to 1 equivalent of the compound represented by the formula (2).

  When a solvent is used, the solvent used may be inert to the reaction. For example, N, N-dimethylformamide, N, N-dimethylacetamide, acetonitrile, dimethyl sulfoxide, 1,3-dimethyl-2-imidazo Polar solvents such as linone, ethers such as diethyl ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane, diphenyl ether, aromatic hydrocarbons such as benzene, toluene, xylene, methylene chloride, chloroform, tetrachloride Examples thereof include halogenated hydrocarbons such as carbon and 1,2-dichloroethane, and aliphatic hydrocarbons such as n-pentane and n-hexane. These solvents may be used alone or as a mixture of two or more thereof.

  When using a base, the base used can be an organic base such as triethylamine, pyridine, 4- (dimethylamino) pyridine, or an inorganic base such as potassium carbonate or sodium carbonate, and is represented by the formula (2). The compound can be used in the range of 0.1 to 50 equivalents per equivalent of the compound.

  When a condensing agent is used, the condensing agent used is 1H-benzotriazol-1-yloxytris (dimethylamino) phosphonium hexafluorophosphate, N, N′-dicyclohexylcarbodiimide, 1- (3-dimethylaminopropyl) -3-Ethylcarbodiimide hydrochloride, 2-chloro-1-methylpyridinium iodide, etc. are mentioned, and it is used in the range of 0.1 to 50 equivalents with respect to 1 equivalent of the compound represented by the formula (2). it can.

  When an additive is used, examples of the additive used include 3H- [1,2,3] triazolo [4,5-b] pyridin-3-ol, 1-hydroxybenzotriazole, and the like. Can be used in the range of 0.1 to 50 equivalents relative to 1 equivalent of the compound represented by formula (1).

  The reaction temperature can be set to any temperature from −78 ° C. to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but is usually in the range of 5 minutes to 100 hours. Can be set.

  Some of the compounds represented by formula (2) are known compounds, and some of them are commercially available.

Some of the compounds represented by the formula (3a) are known compounds and can be synthesized by a method according to a known method described in the literature. Examples of known methods known in the literature include the method described in International Publication No. 2008/006540.
Manufacturing method B
The heterocyclic amide compound represented by the formula (1) can be produced, for example, by reacting the compound represented by the formula (2) with the compound represented by the formula (3b).

Formula (2) [wherein Q and R ³ represent the same meaning as described above. Or a salt thereof and formula (3b) [wherein W and X represent the same meaning as described above, and Xa represents a leaving group such as ^a halogen atom. ] Or a salt thereof in a solvent or in the absence of a solvent, and if necessary, using a base, the compound represented by formula (1) [wherein Q, R ³ , W and X are as defined above. Represents the same meaning. This invention compound represented by this can be manufactured.

  In this reaction, the compound represented by the formula (3b) can be used in the range of 0.1 to 100 equivalents with respect to 1 equivalent of the compound represented by the formula (2).

  When a solvent is used, the solvent used may be inert to the reaction. For example, N, N-dimethylformamide, N, N-dimethylacetamide, acetonitrile, dimethyl sulfoxide, 1,3-dimethyl-2-imidazo Polar solvents such as linone, ethers such as diethyl ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane, diphenyl ether, aromatic hydrocarbons such as benzene, toluene, xylene, methylene chloride, chloroform, tetrachloride Examples thereof include halogenated hydrocarbons such as carbon and 1,2-dichloroethane, and aliphatic hydrocarbons such as n-pentane and n-hexane. These solvents may be used alone or as a mixture of two or more thereof.

  When using a base, the base used is an organic base such as triethylamine, pyridine or 4- (dimethylamino) pyridine, or an inorganic base such as potassium carbonate, sodium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate or sodium hydride. And can be used in the range of 0.1 to 50 equivalents with respect to 1 equivalent of the compound represented by Formula (2). These bases may be used alone, or two or more of these may be mixed and used.

The reaction temperature can be set to any temperature from −78 ° C. to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but is usually in the range of 5 minutes to 100 hours. Can be set.
Reaction formula 1
The compound represented by the formula (3b) can be produced, for example, by reacting the compound represented by the formula (3a) with a halogenating agent.

Formula (3a) [wherein W and X represent the same meaning as described above. And the salt thereof and a halogenating agent in a solvent or without a solvent, and if necessary, using a base, the compound of formula (3b) [wherein W, X and X ^a Represents the same meaning as described above. The compound represented by this can be manufactured.

  Examples of the halogenating agent include thionyl chloride, oxalyl chloride, phosphoryl chloride and the like. As an equivalent of a halogenating agent, it can use in 0.1-100 equivalent with respect to 1 equivalent of compounds represented by Formula (3a).

  When a solvent is used, the solvent used may be inert to the reaction. For example, N, N-dimethylformamide, N, N-dimethylacetamide, acetonitrile, dimethyl sulfoxide, 1,3-dimethyl-2-imidazo Polar solvents such as linone, ethers such as diethyl ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane, diphenyl ether, aromatic hydrocarbons such as benzene, toluene, xylene, methylene chloride, chloroform, tetrachloride Examples thereof include halogenated hydrocarbons such as carbon and 1,2-dichloroethane, and aliphatic hydrocarbons such as n-pentane and n-hexane. These solvents may be used alone or as a mixture of two or more thereof.

  When using a base, the base used is an organic base such as triethylamine, pyridine or 4- (dimethylamino) pyridine, or an inorganic base such as potassium carbonate, sodium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate or sodium hydride. And can be used in the range of 0.1 to 50 equivalents with respect to 1 equivalent of the compound represented by the formula (3a). These bases may be used alone, or two or more of these may be mixed and used.

  The reaction temperature can be set to any temperature from −78 ° C. to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but is usually in the range of 5 minutes to 100 hours. Can be set.

  After completion of the reaction, a production intermediate to be a raw material compound of production method B can be obtained by carrying out usual post-treatment.

  Further, the production intermediate produced by this method can be used as it is in the next step without isolation and purification.

  Specific examples of the active compound included in the present invention include compounds shown in Table 1. However, the compounds in Table 1 are for illustrative purposes, and the present invention is not limited thereto. In the table, the substituent described as Me represents a methyl group, hereinafter, Et represents an ethyl group, n-Pr and Pr-n represent normal propyl groups, i-Pr and Pr-i. Is an isopropyl group, c-Pr and Pr-c are cyclopropyl groups, n-Bu and Bu-n are normal butyl groups, s-Bu and Bu-s are secondary butyl groups, i-Bu and Bu- i represents an isobutyl group, t-Bu and Bu-t represent a tertiary butyl group, t-Bu and Bu-t represent a tertiary butyl group, and Ph represents a phenyl group, respectively.

  In the tables, the substituents represented by J-1 to J-8 each represent the following structure.

[Table 1]

  The compound of the present invention can be used as a herbicide for paddy fields in any treatment method of soil treatment and foliage treatment under flooded water. As paddy field weeds, for example, weeping family (Potamogetonaceatiaceae) represented by Potamogeton distinctus, etc. ) Weeds, Azegaya (Leptochloa chinensis), Echinochloa crus-galli, Echinochloa oryzicola, Hashilochurus japonosum and H. Gramineae weed, Kurowai (Eleocharis kuroguwai), Firefly (Sirpus juncoides), Shizui (Sirpus nipponicus), Cyrus sera (Cyprus seritinus) (Cyperaceae) weeds, duckweeds (Spirodella polyrhiza), duckweeds (Lemna paucicostata) and other species of duckweed (Lemnaceae) weeds, duckweeds (Murdania coenaceae) Weeds (Pontederiaceae) represented by the blue mallow (Monochoria korsakowii) and the white oak (Monochoria vaginalis), and the juveniles of the moss (Elatine triadra) ) And other species such as Lythraceaae, Lydwigia epiobioides, and other species such as Oenotheraceae weeds, Dopatrium junceum, and Grap. sessilifolia), Azena (Lindernia pyxidaria), American Azena (Lindernia dubia) Examples thereof include Compositae weeds represented by Bidens tripartita.

  In addition, the compound of the present invention can be used as a herbicide for upland fields and orchards in any treatment method of soil treatment, soil admixture treatment, and foliage treatment. Examples of upland field weeds include Solanumae weeds represented by Solanum nigrum and Datura stramonium, Solanasae weeds represented by Grunum carolinianum, and Aceaeaceae cereals (Gae) cereals (Gaeumaceae) (Abutilon theophrasti) and malvaaceae weeds represented by Sida spinosa, etc., Ipomoea purpurea, etc. and Ipomoea spps. Convolvulaceae weed, Amaran (Amaran) hus lividus) and slender amaranth (Amaranthus retroflexus) Amaranthaceae represented by such (Amaranthaceae) weeds, cocklebur (xanthium pensylvanicum), ragweed (Ambrosia artemisiaefolia), sunflower (Helianthus annuus), galinsoga quadriradiata (Galinsoga ciliata), western thorns thistle (Cirsium arvense, Sorgio vulgaris, Erigeron annus, and other species of Compositae weeds, Roppa indica, Shirapis arvensis Ca a bursaceae weed, represented by a Bursapastoris, etc. Weeds represented by, for example, Polygonaceae weeds represented by, for example, Polygonum bulvoluis, Polygonum convolvulus, olulaceae, etc. (Portulacaceae) weeds, white-spotted (Chenopodium album), red-breasted (Chenopodium falifolium), weeds (Chenopodiacee) weeds represented by weeds (Cenopodiaceae) The Weeds such as Sphaphulariaceae represented by Veronica persica, Ceminaurae weeds represented by Commelina communis, etc., and Lamium urumiles. Euphorbiaceae (Euphorbiaceae) and other species such as Euphorbiaceae (Galium spurium), representatives of Euphorbiaceula (Euporbiaacea) Rubyaceae Weeds such as Violaceae weeds represented by weeds and violets (Viola mandhurica) and leguminous weeds represented by Sesbania exaltata and Cassia obtusifolia, etc. Representative broad-leaved weeds such as Oxsaldaseae, wild sorghum (Sangham bicolor), Panicum dichotomiflore, Sorghum halepense. crus-galli, Echinochloa crus-galli var. Gramineaceus weeds and Cyperus rotundus typified by Setaria viridis, Aquino noclogosa (Setaria faberi), and Amaranthus aegualis, etc., and Cyperus rotundus et al. Cyperaceae weeds (typical), and the like.

  Further, the compound of the present invention can be used for soil treatment, soil admixture treatment, and foliage treatment in non-agricultural lands such as turf, playground, open space, roadsides, and track ends in addition to the fields of agriculture and horticulture such as paddy fields, upland fields and orchards. It can also be used in the processing method. The weeds include those mentioned in upland and orchard weeds, Poa annua, Taraxacum officinale, Conyzaol samsensis, Cardamine minx, (Hydrocotyl sibthorpioides), Plantago asiatica, Cyperus brevifolia, Kyllinga brevifolia, Equisetum arvense and the like.

  The compound of the present invention may be mixed and applied with other types of herbicides, various insecticides, fungicides, plant growth regulators, synergists, and the like, as necessary, during formulation or spraying.

  In particular, when mixed with other herbicides, cost reduction due to a decrease in the amount of applied medicine, expansion of the herbicidal spectrum due to the synergistic action of the mixed drugs, and higher herbicidal effects can be expected. At this time, a combination with a plurality of known herbicides is also possible.

Preferred herbicides to be used in combination with the compound of the present invention include, for example, acetochlor (acetochlor / generic name), acifluorfen (acifluorfen / generic name), aclonifen (aclonifen / generic name), alachlor (alachlor / (Generic name), alloxidim (alloxydim / generic name), sodium alloxidim-sodium / generic name, ametrine (generic name), amicarbazone (generic name), amidosulfuron (common name), Aminocyclopyrachlor (generic name), salts and esters of aminocyclopyracryl (aminocyclopirachlo) r-salts and esters, aminopyralides (generic names), salts and esters of aminopyralides (aminopyridid-salts and esters), amiprophos-methyl (common names), amitrol (common names) (Anifofos / generic name), ashram (asulam / generic name), atrazine (atrazine / generic name), azaphenidin (azafenidin / generic name), azimusulfuron (generic name), beflubutamid (generic name), beazoline Benazolin-ethyl / generic name), bencarbazone / generic name , Benfluralin (benfulin / generic name), benfrate (benfurateate / generic name), bensulfuron methyl (bensulfuron-methyl / generic name), bensulide (bensulide / generic name), bentazone (sodium name), bentazone (sodium) bentazone-sodium / generic name), bentazone salt (bentazone-salts), benziocarb (general name), benzfendizone (generic name), benzobicyclon (generic name), benzophenap (generic name) benzofenap / generic name), bialaphos (generic name), bialaphos sodium ( bialaphos-sodium / generic name), bicyclopyrone (bicyclopyrone / generic name), bifenox (bifenox / generic name), bispyribac (bispyribac / generic name), bispilibac sodium (bispyribac-sodium / generic name), bromacil (birocil) (Generic name), bromobutide (generic name), bromophenoxime (generic name), bromoxynil (generic name), salts and esters of bromoxynil (general name) and butachlor (general name) , Butafenacil (generic name), butamifos (butamifos) (Generic name), butenachlor (butenachlor / generic name), butralin (butralin / generic name), butroxydim (butoxydim / generic name), butyrate (butylate / generic name), fenfentrol (calfenstrole / generic name), carbetamid (carbetamide / common name) ), Carfentrazone-ethyl, chloromethoxyphene (generic name), chloromethoxynyl (generic name), chloramben (general name), chloramben salts and esters (chloramben-salts and esters) ), Chloransrammethyl l / generic name), chlorflurenol-methyl / generic name, chloridazon / generic name, chlorimuron-ethyl / generic name, chlorobromuron / generic name, Chlorotoluron (generic name), chloroxuron (generic name), chlorphthalim (general name), chloroprofam (general name), chloro IPC (chloroprophlon / generic name), chlorosulfuron (chlorsulfuron) Name), chlorthal dimethyl (general name), chlorthiamid ( hlorthiamid / generic name), sinidone ethyl (cinidon-ethyl / generic name), cinmesulin (generic name), sinosulfuron (cynosulfuron / generic name), cletodim (generic name), clodina hop (generic name) Hoppropargyl (clodinafop-propargyl / generic name), clomazone (clomazone / generic name), clomeprop (cloproprop / generic name), clopyralid (clopyralid / generic name), clopyralid salts and esters (clopyralid-Nsalts, clospandid-salts) (Generic name), cumylron (generic name), cyanazine (cyanazi) / Generic name), cycloate (cycloate / generic name), cyclopyrimoleate (cyclopyrimorate / generic name, SW-065 / study name), cyclosulfamuron (cyclosulfamuron / generic name), cycloxydim (cycloxydim / generic name), Cyhalofop butyl (cyhalofop-butyl / generic name), DAH-500 (test name), darapon (dalapon / generic name), dazomet (dazomet / generic name), desmedifam (desmedifam / generic name), desmethrin (desmetrin) / Common name), dicamba (generic name), dicamba-salts and esters, diclobenil / one ), Diclohop (generic name), diclohop methyl (generic name), dichloroprop (generic name), dichlorprop salts and esters, dichlorprop-salts and esters Chlorprop- (P / generic name), salts and esters of P-dichloroprop-P-salts and esters, dicroslam (diclosulam / generic name), difenzoquat (common name), diflufenic (difluenic) Name), diflufenzopyr (diflufenzopyr / generic name), diflufenzopyr sodium (difluf) nzopyr-sodium / generic name), dimethylpiperate (dimipeperate / generic name), dimetamethrin (dimtammetry / generic name), dimetachlor (dimethachlor / generic name), dimethenamide (dimethenamide / generic name), P-dimethenamide (generic name) , Dimesipine (dimethipine / generic name), dinitroamine (dinitramine / generic name), dinoseb (dinoseb / generic name), dinoteb (dinotarb / generic name), DNOC / generic name, diphenamide (generic name), diquat / Generic name), dithiopyr (dithiopyl / generic name), diuron (diuron / generic name), DSMA / generic name, Daimlon (genom / generic name), Endothal (endothal / generic name), EPTC / generic name, esprocarb (generic name), ethalfluralin (ethalfluralin / generic name), ethamesulfuron-methyl (general name) Name), etofumesate (ethofumesate / generic name), ettobenzanide (etobenzanid / generic name), ethoxysulfuron (ethoxysulfuron / generic name), flazasulfuron (general name), fenoxaprop / generic name, Sapropethyl (fenoxaprop-ethyl / generic name), phenoxasulfone (fenoxasulfone) (Generic name), fenquinotrione (generic name), fentolazamide (general name), flamprop (generic name), flazasulfuron (common name), florasulfuron (generic name), fluazihop (Fluazifop / generic name), fluazifop butyl (fluazifop-butyl / generic name), fluazolate (fluazolate / generic name), flucarbazone sodium (flucarbazone-sodium / generic name), flucetsulfuron / generic name , Fluchloralin (generic name), flufenacet (generic name), Rufenpyrethyl (flufenpyl-ethyl / generic name), flumeturum (flumetsulam / generic name), fluromicrolac-pentyl (generic name), flumioxazin (generic name), fluometuron (generic name) , Fluoroglycofen-ethyl (fluoroglycofen-ethyl / generic name), flupylsulfuron (flupyrsulfuron / generic name), flupoxam (fluoxam / generic name), flulenol (generic name), fluridone (generic name), flurodone / generic name Lydon (flurochloridone / generic name), fluroxypyr (fluroxypyr / generic name), fluro Cypil esters (fluroxypyr-esters), fluprimidol (flurprimidol / generic name), flutamon (flurtamone / generic name), fluthiaset-methyl (generic name), fomesafen (fomesafen / generic name), foramsulfen (Foramsulfuron / generic name), fosamine (fosamine / generic name), glufosinate (glufosinate / generic name), glufosinate-ammonium (generic name), glyphosate (generic name), glyphosate-ammonium Name), glyphosate isopropylamine (glyphos) te-iso-propylamonium / generic name), glyphosate potassium (glyphosate-potassium / generic name), glyphosate sodium (glyphosate-sodium / generic name), glyphosate-trimesium (generic name), axium (Generic name), salts and esters of haloxifene-salts and esters, halosafene (halosafen / generic name), halosulfuron (halosulfuron / generic name), halosulfuron methyl (halosulfuron-methyl / generic name), haloxyhop ( haloxyfop / generic name), haloxyhop methyl (haloxy) op-methyl / generic name), hexazinone (hexazinone / generic name), timer The meta benz methyl (imazamethabenz-methyl / generic name), imazamox (imazamox / generic name), Imazapiku (i
mazapic / common name), imazapyr (common name), imazetapyr (common name), imazaquin (generic name), imazosulfuron (common name), indanophan Common name), iodosulfuron-methyl-sodium / generic name, ioxynyl octanoate / general name, salts and esters of ioxynil-salts and esters, ipfencarbazone / ipfencarbazone Name), isoproturon (common name), iso Ron (isouron / generic name), isoxaben (isoxaben / generic name), isoxaflutol (isoxafulle / generic name), carbutylate (common name), lactofen (generic name), renacil (lenacil / generic name) Linulin (linuron / generic name), maleic hydrazide (generic name), MCPA (generic name), MCPA salts and esters (MCPA-salts and esters), MCPB (generic name), MCPB salts and esters (MCPB-salts and esters), mecoprop (MCPP / generic name), mecoprop salts and esters (mecoprop-salts and e ters), P mecoprop (P, MCPP-P / generic name), salts and esters of P mecoprop (mecoprop-P-salts and esters), mefenacet (generic name), mefluide (mefluidide / generic name), Mesosulfuron-methyl (generic name), mesotrione (metrition / generic name), metam (metam / generic name), metamihop (metamihop / generic name), metamitron (metamitron / generic name), metazachlor (metazalch / general) Name), metabenzthiazuron (general name), metazosulfuron (general name) Name), Methiozoline (generic name), Methyl azide (common name), Methyl bromide (generic name), Methyl dimron (generic name), Methyl iodide (common name) ), Metbenzuron (metobenzuron / generic name), metolachlor (metolachlor / generic name), Smetolachlor (metolachlor-S / generic name), metoslam (metosuram / generic name), metribuzine (metribuzin / generic name), metsulfuron methyl (Metsulfuron-methyl / generic name), methoxuron (generic name / generic name), molinate (generic name / generic name), monolini Uron (monolinuron / generic name), monosulfuron (monosulfuron / generic name), monosulfuron methyl (monosulfuron-methyl / generic name), MSMA / generic name, naproanilide (generic name), napropamide (generic name), napropamide (Naptalam / generic name), naptalam sodium (naptalam-sodium / generic name), nebulon (neburon / generic name), nicosulfuron (nicosulfuron / generic name), norflurazon (norflurazon / generic name), OK-701 (test name) ), Oleic acid (oleic acid / generic name), olven curve (orbencarb / generic name), orthosulfamlone (ort) hosulfamuron / generic name), oryzalin (ordinary / generic name), oxadialgyl (oxadiargyl / generic name), oxadiazon (oxadiazon / generic name), oxasulfuron (generic name), oxadichromemefone / generic name (Oxyfluorfen / generic name), paraquat (paraquat / generic name), pelargonic acid (pelargonic acid / generic name), pendimethalin (pendimethalin / generic name), penoxslam (penoxslam / generic name), pentanochlor (pentanochlor) ), Pentoxazone (general name), petoxamide (petho) amid / generic name), phenmedifam-ethyl / (generic name), picloram (picloram / generic name), salts and esters of picloram (picloram-salts and esters), picolinafen (generic name), pinoxaden ( pinoxaden / generic name), piperophos (piperophos / generic name), pretilachlor (pretilachlor / generic name), primisulfuron-methyl / generic name, prodiamine (generic name), profluazole (profluzol) (Generic name), propoxydim (profoxydim / generic name), prometon (promethon / general) Name), promethrin (prometryn / generic name), propachlor (propachlor / generic name), propanil (propanil / generic name), propoxafop (propaquafop / generic name), propazin (propazin / generic name), profam (profaph) (Generic name), propisochlor (propisochlor / generic name), propoxycarbazone sodium (propoxycarbazone-sodium / generic name), propyrisulfuron (generic name), propizamide (general name), pullulofurbo / General name), prosulfuron (prosulfuron / generic name), pyraclonil / (Generic name), pyraflufen-ethyl (generic name), pyrasulfotol (generic name), pyrazolinate (general name), pyrazosulfuron (generic name), pyrazosulfuron ethyl (pyrazolsulfurethyl) ethyl / generic name), pyrazoxifene (pyrazoxyphen / generic name), pyribenzoxim (pyribenzoxim / generic name), pyributicalcarb (generic name), pyridafol (generic name) Generic name), pyriminobac-methyl / (Generic name), pyrimisulfan (pyrimisulfan / generic name), pyrithiobac sodium (pyrithiobac-sodium / generic name), pyroxasulfone (pyroxasulfone / generic name), piroxisulfam (generic name), quinclorac / quincloclac (Generic name), quinmerac (common name), quinoclamin (common name), quizalofop (common name), quizalofop-ethyl (generic name), quizalofop tefryl tefuryl / generic name), P quizalofop-P / generic name, P quizalofop-P-et hyl / generic name), P quizalofop-p-tefuryl / generic name, rimsulfuron (rimsulfuron / generic name), saflufenacil (saflufenacil / generic name), cetoxydim / generic name siduron / generic name), simazine (simazine / generic name), simethrin (simetlyn / generic name), SL-261 (test name), sulcotrione (sulcotrione / generic name), sulfentrazone (sulfentrazone / generic name), Sulfomethuron methyl (sulfomethuron-methyl / generic name), sulfosulfuron (sulfosulfuron / generic name), TCBA (2,3,6-TBA / generic name), T BA salts and esters (2,3,6-TBA-salts and esters), TCTP (chlor-dimethyl, tetrachlorothiophene / generic name), tebutam (general name), tebuthiuron / generic name, tefril trione (Tefuryltrione / generic name), tembotrione (general name), tepraxidim (general name), terbacil (general name), terbumeton (general name), terbuthylazine (general name) (Terbutryn / generic name), tetrapion te / generic name), tenilchlor (tenylchlor / generic name), thiafluuron (thiazfluron / generic name), thiazopyr (thiazopyr / generic name), thidiazimin (generic name), thidiazuron / generic name (Thiencarbazone-methyl / generic name), thifensulfuron-methyl (generic name), tolpyralate (generic name), topramezone (general name), toloxydim (generic name) / Generic name), trialate (general name), triasulf (Triasulfuron / generic name), triazifram (generic name), tribenuron methyl (tribenuron-methyl / generic name), triclopyr (triclopyrr / generic name), triclopyr salts and esters , Tridiphane (triidiphane / generic name), trietadine (trietazine / generic name), trifludimoxazine (trifludimoxadin / generic name), trifloxysulfuron / generic name, trifluralin (trifluralin / generic name) Sulfuron methyl (triflusulfuron-methyl / generic name), tritosulfuron (tr itosulfuron / generic name), 2,4-PA (generic name), salts and esters of 2,4-PA (2,4-PA-salts and esters), 2,4-D (generic name), 2,4 -D salts and esters (2,4-D-salts and esters), 2,4-DB (generic name), 2,4-DB salts and esters (2,4-DB-salts and esters) and the like Can be mentioned. These components can be used alone or in admixture of two or more, and the ratio in the case of mixing can also be freely selected.

  As the safener, for example, AD-67, Benoxacol (benoxacor / generic name), cloquintocet-mexyl (generic name), ciomethrinil (cyomerinil / generic name), dichlormid (dichlormid / generic name), Dicyclonone (common name), cyprosulfamide (generic name), dietrate (generic name), DKA-24, dimron (common name), fenchlorazole-ethyl (general name) ), Fencrolim (general name), hexime (general name), flurazole (generic name), fluxofeni (Fluxofenim / generic name), flirazole (furilazole / generic name), isoxadifen (isoxadifen / generic name), isoxadifen-ethyl (isoxadifen-ethyl / generic name), MCPA, mecoprop (generic name), mefenpyr (mefenpy) / Generic name), mefenpyr-ethyl (mefenpyr-ethyl / generic name), mefenpyr-diethyl (mefenpyr-diethyl / generic name), mephenate (mephenate / generic name), MG-191, NA (Naphtalic anhydride), OM (Octamethylene-diamin), oxabetrinyl (oxabetrilin / generic name), PPG-1292, R-29148, etc. Can be mentioned. These components can be used alone or in admixture of two or more, and the ratio in the case of mixing can also be freely selected.

  In applying the compound of the present invention as a herbicide, it is usually mixed with a suitable solid carrier or liquid carrier, and if desired, a surfactant, a penetrating agent, a spreading agent, a thickening agent, an antifreezing agent, a binder, a solid carrier. Add anti-caking agent, disintegrant, anti-decomposition agent, etc., and put to practical use in any dosage form such as wettable powder, emulsion, flowable, dry flowable, liquid, powder, granule or gel. be able to. In addition, from the viewpoint of labor saving and safety improvement, the preparation of any dosage form can be enclosed in a water-soluble package.

  Examples of solid carriers include quartz, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite, and diatomaceous earth, and other minerals, calcium carbonate, ammonium sulfate, sodium sulfate, and potassium chloride. Examples include salts, synthetic silicic acid and synthetic silicates.

  Examples of the liquid carrier include alcohols such as ethylene glycol, propylene glycol and isopropanol, aromatic hydrocarbons such as xylene, alkylbenzene and alkylnaphthalene, ethers such as butyl cellosolve, ketones such as cyclohexanone, and esters such as γ-butyrolactone. And acid amides such as N-methylpyrrolidone and N-octylpyrrolidone, vegetable oils such as soybean oil, rapeseed oil, cottonseed oil and castor oil, and water.

  These solid and liquid carriers may be used alone or in combination of two or more.

  Examples of the surfactant include polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene styryl phenyl ether, polyoxyethylene polyoxypropylene block copolymer, polyoxyethylene fatty acid ester, sorbitan fatty acid ester and polyoxyethylene sorbitan. Nonionic surfactant such as fatty acid ester, alkyl sulfate, alkylbenzene sulfonate, lignin sulfonate, alkyl sulfosuccinate, naphthalene sulfonate, alkyl naphthalene sulfonate, salt of formalin condensate of naphthalene sulfonate, Salt of formalin condensate of alkylnaphthalenesulfonic acid, polyoxyethylene alkylaryl ether sulfate and phosphate, polyoxyethylene polystyrene Anionic surfactants such as phenyl ether sulfate and phosphate, polycarboxylate and polystyrene sulfonate, cationic surfactants such as alkylamine salt and alkyl quaternary ammonium salt, and amphoteric interfaces such as amino acid type and betaine type An activator is mentioned.

  The content of these surfactants is not particularly limited, but is usually in the range of 0.05 to 20 parts by mass with respect to 100 parts by mass of the preparation of the present invention. These surfactants may be used alone or in combination of two or more.

  The compound of the present invention may be mixed and applied with other types of herbicides, various insecticides, fungicides, plant growth regulators, synergists, and the like, as necessary, during formulation or spraying.

  In particular, when mixed with other herbicides, cost reduction due to a decrease in the amount of applied medicine, expansion of the herbicidal spectrum due to the synergistic action of the mixed drugs, and higher herbicidal effects can be expected. At this time, a combination with a plurality of known herbicides is also possible.

  The application dose of the compound of the present invention varies depending on the application scene, application time, application method, cultivated crops, etc., but generally an amount of 0.005 to 50 kg per hectare (ha) is appropriate as the amount of active ingredient.

Next, formulation examples of the preparation when the compound of the present invention is used are shown. However, the formulation examples of the present invention are not limited to these. In the following formulation examples, “part” means part by mass.
Wettable compound of the present invention 0.1-80 parts Solid carrier 5-98.9 parts Surfactant 1-10 parts Others 0-5 parts Others include, for example, anti-caking agents and decomposition inhibitors.
Emulsified compound of the present invention 0.1-30 parts Liquid carrier 45-95 parts Surfactant 4.9-15 parts Others 0-10 parts Others include, for example, spreading agents, decomposition inhibitors and the like.
Flowable agent compound of the present invention 0.1 to 70 parts Liquid carrier 15 to 98.89 parts Surfactant 1 to 12 parts Others 0.01 to 30 parts Others include, for example, antifreezing agents and thickeners. It is done.
Dry flowable agent compound of the present invention 0.1-90 parts Solid carrier 0-98.9 parts Surfactant 1-20 parts Others 0-10 parts Others include, for example, binders, decomposition inhibitors, etc. .
Liquid compound of the present invention 0.01 to 70 parts Liquid carrier 20 to 99.99 parts Others 0 to 10 parts Others include, for example, antifreezing agents and spreading agents.
Granules of the present invention compound 0.01 to 80 parts Solid carrier 10 to 99.99 parts Others 0 to 10 parts Others include, for example, binders and decomposition inhibitors.
Powder Compound of the Present Invention 0.01-30 parts Solid carrier 65-99.99 parts Others 0-10 parts Others include, for example, drift inhibitors and decomposition inhibitors.

  In use, the preparation is sprayed as it is or diluted 1 to 10,000 times with water.

Formulation Examples Next, specific examples of agrochemical formulations containing the compound of the present invention as an active ingredient are shown, but the invention is not limited thereto. In the following formulation examples, “parts” means parts by weight.
[Formulation Example 1] Wetting Agent Compound No. 1-001 20 parts Pyrophyllite 76 parts Solpol 5039 2 parts (Anionic surfactant: Toho Chemical Industries, Ltd. trade name)
Carplex # 80 2 parts (Synthetic hydrous silicate: Shionogi Pharmaceutical Co., Ltd. trade name)
The above is uniformly mixed and ground to obtain a wettable powder.
[Formulation Example 2] Emulsion The present compound No. 1-001 5 parts Xylene 75 parts N-methylpyrrolidone 15 parts Solpol 2680 5 parts (anionic surfactant: Toho Chemical Industries, Ltd. trade name)
The above is uniformly mixed to obtain an emulsion.
[Composition Example 3] Flowable Agent Compound No. 1-001 25 parts Agrisol S-710 10 parts (Nonionic surfactant: trade name of Kao Corporation)
Lnox 1000C 0.5 part (anionic surfactant: Toho Chemical Co., Ltd. trade name)
Xanthan gum 0.02 parts Water 64.48 parts After uniformly mixing the above, wet milling to obtain a flowable agent.
[Composition Example 4] Dry flowable agent Compound No. 1-001 75 parts Hightenol NE-15 5 parts (Anionic surfactant: Daiichi Kogyo Seiyaku Co., Ltd. trade name)
Vanillex N 10 parts (anionic surfactant: Nippon Paper Industries Co., Ltd. trade name)
Carplex # 80 10 parts (Synthetic hydrous silicic acid: Shionogi Pharmaceutical Co., Ltd. trade name)
After uniformly mixing and pulverizing the above, a small amount of water is added and stirred and kneaded, granulated with an extrusion granulator, and dried to obtain a dry flowable agent.
[Formulation Example 5] Granule The present compound No. 1-001 1 part Bentonite 55 parts Talc 44 parts After uniformly mixing and pulverizing the above, a small amount of water is added and mixed with stirring, kneaded, granulated with an extrusion granulator, and dried to form granules.

  In the present invention, the present invention will be described in more detail by specifically describing the synthesis examples and test examples of the heterocyclic amide compound represented by the formula (1) as examples, but the present invention is limited by these. Is not to be done.

  The medium pressure preparative liquid chromatography described in the synthesis examples and the reference examples used Yamazen Corporation medium pressure preparative device; YFLC-Wprep (flow rate 10 ml / min, silica gel 40 μm column).

Moreover, the proton nuclear magnetic resonance chemical shift value of the Example was measured at 300 MHz using Me ₄ Si (tetramethylsilane) as a reference material. Moreover, the solvent used for the measurement is described in the following synthesis examples. Moreover, the symbol in the proton nuclear magnetic resonance chemical shift value of an Example represents the following meaning.
s: singlet, d: doublet, dd: double doublet, dt: double triplet, t: triplet, q: quartet, m: multiplet, br: broad synthesis example [synthesis example 1]
N- (1,3,4-oxadiazol-2-yl) -3-[(N-methylmethylsulfonamido) methyl] -5- (trifluoromethyl)-[1,2,4] triazolo [4 , 3-a] Synthesis of pyridine-8-carboxamide (Compound No. 1-001) 3-[(N-methylmethylsulfonamido) methyl] -5- (trifluoromethyl)-[1,2,4] triazolo [4,3-a] pyridine-8-carboxylic acid 110 mg (0.31 mmol), 1,3,4-oxadiazol-2-amine 40 mg (0.47 mmol), 1-hydroxy-7-azabenzotriazole 65 mg 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride 90 at room temperature in a mixed solution of (0.48 mmol) and 2 ml of N, N-dimethylformamide. mg (0.47 mmol) was added. After the addition was complete, the reaction mixture was stirred at room temperature for 15 hours. After completion of the stirring, the solvent in the reaction mixture was distilled off under reduced pressure. To the obtained residue, 10 ml of 0.1 mol / L hydrochloric acid aqueous solution was added at room temperature. The precipitated solid was collected by filtration and washed with water to obtain 100 mg of the desired product as a white solid.
Melting point: 243-245 ° C
[Synthesis Example 2]
N- (1-methyl-1H-tetrazol-5-yl) -3-[(N-methylmethylsulfonamido) methyl] -5- (trifluoromethyl)-[1,2,4] triazolo [4,3 -A] Synthesis of pyridine-8-carboxamide (Compound No. 3-001) 3-[(N-methylmethylsulfonamido) methyl] -5- (trifluoromethyl)-[1,2,4] triazolo [4 , 3-a] Pyridine-8-carboxylic acid 50 mg (0.14 mmol), 1-methyl-1H-tetrazol-5-amine 30 mg (0.30 mmol) and pyridine 1 ml were mixed with thionyl chloride under ice-cooling. 35 mg (0.29 mmol) was added. After the addition was complete, the reaction mixture was stirred at room temperature for 15 hours. After completion of the stirring, the solvent in the reaction mixture was distilled off under reduced pressure. To the obtained residue, 10 ml of 0.1 mol / L hydrochloric acid aqueous solution was added at room temperature. The precipitated solid was collected by filtration and washed with water to obtain 45 mg of the desired product as a white solid.
Melting point: 264-266 ° C
[Synthesis Example 3]
N- (5-methyl-1,3,4-oxadiazol-2-yl) -3-[(N-methylisobutylamido) methyl] -5- (trifluoromethyl)-[1,2,4] Synthesis of triazolo [4,3-a] pyridine-8-carboxamide (Compound No. 2-038) Step 1; N- (5-methyl-1,3,4-oxadiazol-2-yl) -3- Synthesis of [(Methylamino) methyl] -5- (trifluoromethyl)-[1,2,4] triazolo [4,3-a] pyridine-8-carboxamide Methyl [{8-((5-Methyl-1 , 3,4-oxadiazol-2-yl) carbamoyl) -5- (trifluoromethyl)-[1,2,4] triazolo [4,3-a] pyridin-3-yl} methyl] carbamate Libutyl 537mg (1.18m ol) and a mixed solution of methylene chloride 3ml, trifluoroacetic acid was added 3ml at room temperature. After the addition was complete, the reaction mixture was stirred at room temperature for 1 hour. After completion of the stirring, the solvent in the reaction mixture was distilled off under reduced pressure to obtain 663 mg of a mixture of the target compound and trifluoroacetic acid as a yellow solid.
¹ H-NMR (DMSO-d ₆ ); δ 9.58 (s, 1H), 8.21 (d, 1H, J = 7.4 Hz), 8.01 (d, 1H, J = 7.0 Hz), 4.72 (s, 2H), 2.88 (s, 3H), 2.51 (s, 3H). (The proton signals of CONH and CO ₂ H were not observed.)
Step 2; N- (5-Methyl-1,3,4-oxadiazol-2-yl) -3-[(N-methylisobutyramide) methyl] -5- (trifluoromethyl)-[1,2 , 4] Synthesis of triazolo [4,3-a] pyridine-8-carboxamide N- (5-methyl-1,3,4-oxadiazol-2-yl) containing trifluoroacetic acid obtained in step 1 -3-[(Methylamino) methyl] -5- (trifluoromethyl)-[1,2,4] triazolo [4,3-a] pyridine-8-carboxamide 150 mg, triethylamine 97 mg (0.96 mmol) and tetrahydrofuran To 3 ml of the mixed solution, 41 mg (0.39 mmol) of isobutyryl chloride was added at room temperature. After the addition was complete, the reaction mixture was stirred at room temperature for 1 hour. After completion of the stirring, 30 ml of 0.01 mol / L hydrochloric acid was added to the reaction mixture to stop the reaction, followed by extraction with chloroform (30 ml × 2 times). The obtained organic layer was washed with water, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 55 mg of the desired product as a white solid.
Melting point: 184-185 ° C
The compound of the present invention can be synthesized according to the above synthesis examples. Although the example of this invention compound manufactured similarly to the synthesis example 1 thru | or the synthesis example 3 is shown to a 2nd table | surface to a 4th table | surface, this invention is not limited only to these. In the table, “Me” represents a methyl group, and similarly, Et represents an ethyl group, Pr represents a propyl group, Bu represents a butyl group, Ph represents a phenyl group, n− represents normal, i− Means iso, t- means tertiary, and c- means cyclo.

  In the table, “mp” represents a melting point, and “* 1” represents “resin”.

  Moreover, the substituent represented by U-1a, U-3a, U-4a, U-6a, V-1a in a table | surface represents the following structure, respectively.

[Table 2]

―――――――――――――――――――――――――――――
No. R ^1a mp (℃)
―――――――――――――――――――――――――――――
1-001 CH ₂ N (Me) SO ₂ Me 243-245
1-002 CH ₂ N (Me) SO ₂ Et 196-198
1-003 CH ₂ N (Et) SO ₂ Me 238-239
1-004 CH ₂ N (c-Pr) SO ₂ Me 256-257
1-005 CH (Me) N (Me) SO ₂ Me 77-79
1-006 CH ₂ CH ₂ N (Me) SO ₂ Me 162-164
1-007 CH ₂ (U-3a) 160-163
1-008 CH ₂ (U-4a) 127-128
1-009 CH ₂ N (Me) SO ₂ N (Me) ₂ 220-222
1-010 SCH ₂ CH ₂ N (Me) SO ₂ Me 201-202
1-011 CH ₂ N (Me) CO ₂ Me 151-152
1-012 CH ₂ N (Ph) SO ₂ Me 168-170
1-013 CH ₂ N (CH ₂ C≡CH) SO ₂ Me 173-175
1-014 CH ₂ N (i-Pr) SO ₂ Me 228-229
1-015 CH ₂ N (n-Pr) SO ₂ Me 220-221
1-016 CH ₂ N (CH ₂ CH ₂ OMe) SO ₂ Me 177-180
1-017 CH ₂ N (OMe) SO ₂ Me * 1
1-018 CH ₂ N (Me) SO ₂ i-Pr 239-240
1-019 V-1a 261-262
1-020 CH (Me) N (i-Pr) SO ₂ Me 115-118
1-021 CH ₂ N (i-Pr) SO ₂ N (Me) ₂ 132-133
1-022 CH ₂ (U-6a) 219-222
1-023 CH ₂ N (Me) CO ₂ Et 179-181
1-024 CH ₂ N (Et) C (O) Me 168-170
1-025 CH ₂ N (Me) C (O) Et 140-143
1-026 CH ₂ N (Me) C (O) n-Pr 153-155
1-027 CH ₂ N (Me) C (O) i-Pr 199-201
1-028 CH ₂ N (Me) C (O) c-Pr 213-215
1-029 CH ₂ N (Me) C (O) CF ₃ 153-155
1-030 CH ₂ (U-1a) 209-211
1-031 SCH ₂ N (Me) SO ₂ Me 194-195
―――――――――――――――――――――――――――――
[Table 3]

―――――――――――――――――――――――――――――
No. R ^1a mp (℃)
―――――――――――――――――――――――――――――
2-001 CH ₂ N (Me) SO ₂ Me 102-103
2-002 CH ₂ N (Me) SO ₂ Et 178-180
2-003 CH ₂ N (Et) SO ₂ Me 197-199
2-004 CH ₂ N (c-Pr) SO ₂ Me 236-237
2-005 CH ₂ N (i-Pr) SO ₂ Me 262-263
2-006 CH (Me) N (Me) SO ₂ Me 166-167
2-007 CH ₂ CH ₂ N (Me) SO ₂ Me * 1
2-008 CH ₂ (U-3a) 204-207
2-009 CH ₂ (U-4a) 196-197
2-010 CH ₂ N (Me) SO ₂ N (Me) ₂ 132-133
2-011 SCH ₂ CH ₂ N (Me) SO ₂ Me 183-184
2-012 CH ₂ NHC (O) i-Pr 112-119
2-013 CH ₂ N (Me) C (O) Me 144-145
2-014 CH ₂ N (Me) CO ₂ Me 150-151
2-015 CH ₂ NHSO ₂ Me * 1
2-016 CH ₂ N (Ph) SO ₂ Me 221-222
2-017 CH ₂ N (CH ₂ C≡CH) SO ₂ Me 213-215
2-018 CH ₂ N (n-Pr) SO ₂ Me 205-206
2-019 CH ₂ N (CH ₂ CF ₃ ) SO ₂ Me 192-194
2-020 CH ₂ N (CH ₂ C≡N) SO ₂ Me 206-208
2-021 CH ₂ N (CH ₂ CH ₂ OMe) SO ₂ Me 154-156
2-022 CH ₂ N (OMe) SO ₂ Me * 1
2-023 CH ₂ N (Me) SO ₂ CF ₃ 161-162
2-024 CH ₂ N (Me) SO ₂ n-Pr 181-182
2-025 CH ₂ N (Me) SO ₂ i-Pr 185-186
2-026 V-1a 261-262
2-027 CH (Me) N (i-Pr) SO ₂ Me 89-90
2-028 CH ₂ N (i-Pr) SO ₂ N (Me) ₂ 226-227
2-029 CH ₂ (U-6a) 215-219
2-030 CH ₂ N (Me) CO ₂ Et 179-181
2-031 CH ₂ N (i-Pr) CO ₂ t-Bu 110-113
2-033 CH ₂ N (Et) C (O) Me 65-67
2-034 CH ₂ N (i-Pr) C (O) Me 154-158
2-035 CH ₂ N (i-Pr) C (O) Et * 1
2-036 CH ₂ N (Me) C (O) Et 167-169
2-037 CH ₂ N (Me) C (O) n-Pr 144-146
2-038 CH ₂ N (Me) C (O) i-Pr 184-185
2-039 CH ₂ N (Me) C (O) c-Pr 233-235
2-040 CH ₂ N (Me) C (O) CH ₂ Cl 67-70
2-041 CH ₂ N (Me) C (O) CH ₂ SMe 118-119
2-042 CH ₂ N (i-Pr) C (O) CH ₂ SMe 167-171
2-043 CH ₂ N (i-Pr) C (O) CH ₂ SEt * 1
2-044 CH ₂ N (Me) C (O) CF ₃ 166-168
2-045 CH ₂ N (SO ₂ Me) C (O) Me 220-222
2-046 CH ₂ N (Me) C (O) NHEt 156-157
2-047 CH ₂ N (i-Pr) C (O) NHEt 210-212
2-048 CH ₂ N (Me) C (O) N (Me) ₂ 155-156
2-049 CH ₂ N (i-Pr) C (O) N (Me) ₂ 206-208
2-050 CH ₂ N (Me) C (S) NHMe 198-199
2-051 CH ₂ (U-1a) 209-211
2-052 SCH ₂ N (Me) SO ₂ Me 176-178
2-053 CH ₂ N (Me) CO ₂ t-Bu * 1
―――――――――――――――――――――――――――――
[Table 4]

―――――――――――――――――――――――――――――
No. R ^1a mp (℃)
―――――――――――――――――――――――――――――
3-001 CH ₂ N (Me) SO ₂ Me 264-266
3-002 CH ₂ N (Me) SO ₂ Et 218-220
3-003 CH ₂ N (Et) SO ₂ Me 198-200
3-004 CH ₂ N (c-Pr) SO ₂ Me 209-210
3-005 CH ₂ N (i-Pr) SO ₂ Me 84-85
3-006 CH (Me) N (Me) SO ₂ Me 223-225
3-007 CH ₂ CH ₂ N (Me) SO ₂ Me 160-162
3-008 CH ₂ (U-3a) 95-96
3-009 CH ₂ (U-4a) 92-94
3-010 CH ₂ N (Me) SO ₂ N (Me) ₂ * 1
3-011 SCH ₂ CH ₂ N (Me) SO ₂ Me * 1
3-012 CH ₂ N (Me) C (O) Me * 1
3-013 CH ₂ N (Me) CO ₂ Me * 1
3-014 CH ₂ NHSO ₂ Me * 1
3-015 CH ₂ N (Ph) SO ₂ Me 84-85
3-016 CH ₂ N (CH ₂ C≡CH) SO ₂ Me 188-189
3-017 CH ₂ N (n-Pr) SO ₂ Me 195-196
3-018 CH ₂ N (CH ₂ CH ₂ OMe) SO ₂ Me 160-161
3-019 CH ₂ N (OMe) SO ₂ Me * 1
3-020 CH ₂ N (Me) SO ₂ CF ₃ 201-202
3-021 CH ₂ N (Me) SO ₂ i-Pr 120-121
3-022 V-1a 178-179
3-023 CH (Me) N (i-Pr) SO ₂ Me 145-147
3-024 CH ₂ N (i-Pr) SO ₂ N (Me) ₂ * 1
3-025 CH ₂ (U-6a) * 1
3-026 CH ₂ N (i-Pr) C (O) Me 96-102
3-027 CH ₂ N (Me) C (O) Et * 1
3-028 CH ₂ N (SO ₂ Me) C (O) Me 131-133
3-029 SCH ₂ N (Me) SO ₂ Me 194-195
―――――――――――――――――――――――――――――
Table ¹ shows ¹ H-NMR data of the compounds of the present invention without any melting point.

The proton nuclear magnetic resonance chemical shift value was measured at 300 MHz in deuterated chloroform solvent using Me ₄ Si (tetramethylsilane) as a reference substance. The symbols in Table 5 have the following meanings. s: singlet, d: doublet, dd: double doublet, t: triplet, q: quartet, m: multiplet, br: broad.
[Table 5]
――――――――――――――――――――――――――――――――――――――
No. ¹ H-NMR (CDCl ₃ , Me ₄ Si, 300 MHz)
――――――――――――――――――――――――――――――――――――――
1-017 δ12.90 (brs, 1H), 8.53 (d, 1H, J = 7.4Hz), 8.34 (s, 1H), 7.74 (d, 1H,
J = 7.4Hz), 5.04 (s, 2H), 3.69 (s, 3H), 3.15 (s, 3H).
2-007 δ12.79 (brs, 1H), 8.42 (d, 1H, J = 6.3Hz), 7.65 (d, 1H, J = 7.0Hz), 3.94
(t, 2H, J = 7.4Hz), 3.55 (t, 2H, J = 10.0Hz), 3.05 (s, 3H),
2.90 (s, 3H), 2.58 (s, 3H).
2-015 δ12.75 (brs, 1H), 8.46 (d, 1H, J = 7.4Hz), 7.69 (d, 1H, J = 7.4Hz), 6.05
(brs, 1H), 4.99 (d, 2H, J = 5.5Hz), 3.13 (s, 3H), 2.58 (s, 3H).
2-022 δ12.75 (brs, 1H), 8.11 (d, 1H, J = 7.4Hz), 7.57 (d, 1H, J = 7.4Hz), 5.08
(s, 2H), 4.13 (s, 3H), 3.60 (s, 3H), 3.13 (s, 3H).
2-035 δ8.45-8.20 (m, 1H), 7.70-7.50 (m, 1H), 4.87 (s, 2H), 4.50-4.30 (m, 1
H), 2.56-2.35 (m, 3H), 2.60-2.45 (m, 2H), 1.45-1.10 (m, 9H). (CO
The NH proton peak was not observed. )
2-043 δ8.40 (d, 1H, J = 7.2Hz), 7.62 (d, 1H, J = 7.2Hz), 4.85 (s, 2H), 4.55-
4.40 (m, 1H), 3.47 (s, 2H), 2.72 (q, 2H, J = 7.5Hz), 2.57 (s, 3H),
1.39 (d, 6H, J = 6.6Hz), 1.30 (t, 3H, J = 7.5Hz). (The proton signal of CONH was not observed.)
2-053 δ12.84 (brs, 1H), 8.44 (d, 1H, J = 7.0Hz), 7.68 (d, 1H, J = 7.0Hz), 4.98
(s, 2H), 3.21 (s, 3H), 2.58 (d, 3H, J = 3.3Hz), 1.52 (s, 9H).
3-010 δ12.39 (brs, 1H), 8.41 (d, 1H, J = 7.0Hz), 7.71 (d, 1H, J = 7.4Hz), 4.99
(s, 2H), 4.09 (s, 3H), 3.16 (s, 3H), 2.88 (s, 6H),
2.91-2.79 (m, 1H), 2.69-2.48 (m, 2H).
3-011 δ12.39 (brs, 1H), 8.33 (d, 1H, J = 6.6Hz), 7.59 (d, 1H, J = 6.6Hz),
3.70-3.55 (m, 4H), 2.97 (s, 3H), 2.88 (s, 3H), 2.82 (s, 3H),
2.49-2.40 (m, 1H).
3-012 δ12.39 (brs, 1H), 8.39 (d, 1H, J = 7.0Hz), 7.66 (d, 1H, J = 7.0Hz), 5.08
(s, 2H), 4.09 (s, 3H), 3.38 (s, 3H), 2.26 (s, 3H).
3-013 δ12.45 (brs, 1H), 8.40 (d, 1H, J = 7.4Hz), 7.66 (d, 1H, J = 7.4Hz), 5.01
(s, 2H), 4.10 (s, 3H), 3.78-3.71 (m, 3H), 3.24 (s, 3H).
3-014 δ12.23 (brs, 1H), 8.43 (d, 1H, J = 7.4Hz), 7.71 (d, 1H, J = 7.4Hz), 6.01
(brs, 1H), 5.05-4.95 (m, 2H), 4.09 (s, 3H), 3.11 (s, 3H).
3-019 δ12.35 (brs, 1H), 8.47 (d, 1H, J = 7.4Hz), 7.75 (d, 1H, J = 7.4Hz), 5.07
(s, 2H), 4.11 (s, 3H), 3.66 (s, 3H), 3.13 (s, 3H).
3-024 δ12.47 (brs, 1H), 8.39 (d, 1H, J = 7.4Hz), 7.66 (d, 1H, J = 7.4Hz), 4.85
(s, 2H), 4.15-4.05 (m, 4H), 2.92 (s, 6H), 1.33 (d, 6H, J = 6.6Hz).
3-025 δ12.39 (brs, 1H), 8.44 (d, 1H, J = 7.2Hz), 7.69 (d, 1H, J = 7.2Hz), 4.97
(s, 2H), 4.11 (s, 3H), 3.58 (t, 2H, J = 5.7Hz), 3.49 (t, 2H, J = 5.7Hz),
2.87 (s, 3H), 2.05-1.90 (m, 2H).
3-027 δ12.39 (brs, 1H), 8.38 (d, 1H, J = 7.4Hz), 7.66 (d, 1H, J = 7.4Hz), 5.09
(s, 2H), 4.09 (s, 3H), 3.38 (s, 3H), 2.54 (q, 2H, J = 7.4Hz), 1.19 (t,
3H, J = 7.4Hz).
――――――――――――――――――――――――――――――――――――――
[Reference Example 1]
Synthesis of 3-[(N-methylmethylsulfonamido) methyl] -5- (trifluoromethyl)-[1,2,4] triazolo [4,3-a] pyridine-8-carboxylic acid Step 1; Synthesis of ethyl [(N-methylmethylsulfonamido) methyl] -5- (trifluoromethyl)-[1,2,4] triazolo [4,3-a] pyridine-8-carboxylate 3- (Chloromethyl) 250 mg (0.81 mmol) of ethyl 5- (trifluoromethyl)-[1,2,4] triazolo [4,3-a] pyridine-8-carboxylate, 140 mg (1.01 mmol) of potassium carbonate and N, N -To a mixed solution of 10 ml of dimethylformamide, 110 mg (1.01 mmol) of N-methylmethanesulfonamide was added at room temperature. After the addition was complete, the reaction mixture was stirred at room temperature for 15 hours. After completion of the stirring, 20 ml of water was added to the reaction mixture to stop the reaction, and the mixture was extracted with ethyl acetate (20 ml × 2 times). The obtained organic layer was washed with water and then dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane: ethyl acetate [gradient of 7: 3 to 1: 9 (volume ratio, hereinafter the same)] to obtain 135 mg of the desired product. Was obtained as a white solid.
Melting point: 162-163 ° C
Step 2: Synthesis of 3-[(N-methylmethylsulfonamido) methyl] -5- (trifluoromethyl)-[1,2,4] triazolo [4,3-a] pyridine-8-carboxylic acid 3- 135 mg (0.36 mmol) of ethyl [(N-methylmethylsulfonamido) methyl] -5- (trifluoromethyl)-[1,2,4] triazolo [4,3-a] pyridine-8-carboxylate and 1 To a mixed solution of 10 ml of 1,4-dioxane, 0.5 ml of 1 mol / L sodium hydroxide aqueous solution was added at room temperature. After the addition was complete, the reaction mixture was stirred at room temperature for 1 hour. After completion of the stirring, 10 ml of a 0.1 mol / L hydrochloric acid aqueous solution was added to the reaction mixture to stop the reaction, followed by extraction with chloroform (20 ml × 2 times). The obtained organic layer was washed with water, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 110 mg of the desired product as a white solid.
Melting point: 169-171 ° C
[Reference Example 2]
Synthesis of 3- {2- (N-methylmethylsulfonamido) ethyl} -5- (trifluoromethyl)-[1,2,4] triazolo [4,3-a] pyridine-8-carboxylic acid Step 1; Synthesis of ethyl 2- [2- {3- (N-methylmethylsulfonamido) propanoyl} hydrazinyl] -6- (trifluoromethyl) nicotinate 750 mg of ethyl 2-hydrazinyl-6- (trifluoromethyl) nicotinate (3 .01 mmol), 650 mg (3.59 mmol) of 3- (N-methylmethylsulfonamido) propanoic acid, 41 mg (0.30 mmol) of 1-hydroxy-7-azabenzotriazole and 7.5 ml of N, N-dimethylformamide To the solution was added 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride 690 at room temperature. g a (3.60mmol) was added. After the addition was complete, the reaction mixture was stirred at room temperature for 1 hour. After completion of the stirring, 10 ml of a 1 mol / L hydrochloric acid aqueous solution was added to the reaction mixture to stop the reaction, followed by extraction with chloroform (20 ml × 2 times). The obtained organic layer was washed with water, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 1.42 g of a mixture of the desired product and N, N-dimethylformamide as a yellow liquid.
¹ H-NMR (CDCl ₃ ); δ 9.78 (d, 1H, J = 4.1 Hz), 8.39-8.30 (m, 2H), 7.08 (d, 1H, J = 7.7 Hz) ), 4.41 (q, 2H, J = 7.1 Hz), 3.55 (t, 2H, J = 6.8 Hz), 2.93 (s, 3H), 2.84 (s, 3H), 2.69 (t, 2H, J = 6.8 Hz), 1.41 (t, 3H, J = 7.2 Hz).
Step 2: Synthesis of 3- {2- (N-methylmethylsulfonamido) ethyl} -5- (trifluoromethyl)-[1,2,4] triazolo [4,3-a] pyridine-8-carboxylic acid 1.42 g of an N, N-dimethylformamide mixture of ethyl 2- [2- {3- (N-methylmethylsulfonamido) propanoyl} hydrazinyl] -6- (trifluoromethyl) nicotinate obtained in Step 1; To a mixed solution of 1.81 g (6.90 mmol) of phenylphosphine and 20 ml of tetrahydrofuran, 1.79 g (13.85 mmol) of N, N-diisopropylethylamine and 1.63 g (6.89 mmol) of hexachloroethane were added under ice cooling. did. After the addition was complete, the reaction mixture was stirred at room temperature for 1 hour. After completion of the stirring, the solvent in the reaction mixture was distilled off under reduced pressure. To the obtained residue, 12 ml of 1,4-dioxane and 9 ml of 1 mol / L aqueous sodium hydroxide solution were added at room temperature. After the addition was complete, the reaction mixture was stirred at room temperature for 3 hours. After completion of stirring, 10 ml of water was added to stop the reaction, and the mixture was washed with ethyl acetate (20 ml × 4 times). To the obtained aqueous layer, 6 ml of a 1 mol / L hydrochloric acid aqueous solution was added at room temperature, followed by extraction with chloroform (30 ml × 3 times). The obtained organic layer was washed with water and then dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The precipitated solid was collected by filtration and washed with diisopropyl ether to obtain 652 mg of the desired product as a yellow solid.
Melting point: 153-154 ° C
Although the example of this invention compound manufactured similarly to the reference example 1 thru | or the reference example 2 is shown in Table 6 thru | or Table 7, this invention is not limited only to these. In the table, “Me” represents a methyl group, and similarly, Et represents an ethyl group, Pr represents a propyl group, Bu represents a butyl group, Ph represents a phenyl group, n− represents normal, i− Means iso, t- means tertiary, and c- means cyclo.

  In the table, “mp” represents a melting point, and “* 1” represents “resin”.

  Moreover, the substituent represented by U-1a, U-3a, U-4a, U-6a, V-1a in a table | surface represents the following structure, respectively.

[Table 6]

―――――――――――――――――――――――――――――
No. R ^1a mp (℃)
―――――――――――――――――――――――――――――
A-001 CH ₂ N (Me) SO ₂ Me 169-171
A-002 CH (Me) N (Me) SO ₂ Me 173-174
A-003 CH ₂ CH ₂ N (Me) SO ₂ Me 153-154
A-004 CH ₂ (U-3a) 146-148
A-005 CH ₂ (U-4a) 90-91
A-006 CH ₂ (U-6a) 167-170
A-007 CH ₂ NHC (O) i-Pr * 1
A-008 CH ₂ N (Me) CO ₂ t-Bu * 1
―――――――――――――――――――――――――――――
[Table 7]

―――――――――――――――――――――――――――――
No. R ^1a mp (℃)
―――――――――――――――――――――――――――――
B-001 CH ₂ N (Me) SO ₂ Me 162-163
B-002 CH (Me) N (Me) SO ₂ Me 57-58
B-003 CH ₂ (U-3a) 152-153
B-004 CH ₂ (U-4a) * 1
B-005 CH ₂ NHC (O) i-Pr 175-178
B-006 CH ₂ N (Me) CO ₂ t-Bu * 1
―――――――――――――――――――――――――――――
In Tables 6 and 7, ¹ H-NMR data of compounds without melting point are shown in Table 8.
[Table 8]
――――――――――――――――――――――――――――――――――――――
No. ¹ H-NMR (CDCl ₃ , Me ₄ Si, 300 MHz)
――――――――――――――――――――――――――――――――――――――
A-007 δ8.32 (d, 1H, J = 7.4Hz), 7.66 (d, 1H, J = 7.4Hz), 6.85 (brs, 1H), 5.04
(d, 2H, J = 3.9Hz), 2.63-2.55 (m, 1H), 1.28 (d, 6H, J = 6.8Hz). (CO ₂
The proton signal of H was not observed. )
A-008 δ8.26 (d, 1H, J = 7.0Hz), 7.62 (d, 1H, J = 7.0Hz), 4.96 (s, 2H), 3.18 (s,
3H), 1.51 (s, 9H). (The proton signal of CO ₂ H was not observed.)
B-004 δ8.01 (d, 1H, J = 7.4Hz), 7.51 (d, 1H, J = 7.4Hz), 5.01 (s, 2H), 4.59 (q,
2H, J = 7.4Hz), 3.60-3.51 (m, 2H), 3.32-3.24 (m, 2H), 2.34-2.25 (m, 2H)
, 1.99-1.87 (m, 2H), 1.50 (t, 3H, J = 7.4Hz).
B-006 δ7.97 (d, 1H, J = 7.0Hz), 7.46 (d, 1H, J = 7.0Hz), 4.93 (s, 2H), 4.56 (q,
2H, J = 7.1Hz), 3.16 (s, 3H), 1.48 (s, 9H), 1.26 (t, 3H, J = 7.1Hz).
――――――――――――――――――――――――――――――――――――――
Test Example Next, the usefulness of the compound of the present invention as a herbicide will be specifically described in the following test examples, but the present invention is not limited thereto.
[Test Example 1] Herbicidal effect test by pretreatment of weed generation under flooded conditions After alluvial soil was put into a 1/10000 are Wagner pot, water was added and mixed to create a flooded condition with a depth of 4 cm. After seeding nobies, firefly and koigi in the cup, rice seedlings at the 2.5 leaf stage were transplanted. On the day of sowing, the emulsion of the compound of the present invention prepared according to Formulation Example 2 was diluted with water to a predetermined dose and treated on the water surface. Plants were grown by placing the cup in a greenhouse at 25 to 30 ° C., and after 3 weeks of drug treatment, the effects on various plants were investigated according to the following criteria. The results are shown in Table 9.

Criterion 5 ... More than 90% of herbicide rate (almost completely dead)
4 ... Herbicidal Rate 70% or more and less than 90% 3 ... Herbicidal Rate 40% or more and less than 70% 2 ... Herbicidal Rate 20% or more and less than 40% 1 ... Herbicidal Rate 5% or more but less than 20% 0 ... Herbicidal Rate 5% or less (almost effective) None)
[Test Example 2] Herbicidal effect test by treatment with weed growing season in flooded condition After alluvial soil was put into a 1/10000 are Wagner pot, water was added and mixed to obtain a flooded condition of 4 cm in water depth. Nobies, firefly, and oak seeds were mixed in the cup and placed in a greenhouse at 25-30 ° C. to grow plants. When Nobies, Firefly and Konagi reached the 1st to 2nd leaf stage, the emulsion of the compound of the present invention prepared according to Formulation Example 2 was diluted with water so as to have a predetermined dosage and treated on the water surface. Three weeks after the drug treatment, the influence on various plants was investigated according to the criteria of Test Example 1. The results are shown in Table 10.
[Test Example 3] Herbicidal effect test by foliar treatment After alluvial soil was put into a 1/10000 are Wagner pot, water was added and mixed to obtain a condition of water depth of 0.1 to 0.5 cm. Inobie, Azegaya, Kogomegatsutsu and rice seeds were sown and placed in a greenhouse at 25 to 30 ° C. to grow plants. After growing for 14 days, the emulsion of the compound of the present invention prepared according to Formulation Example 2 was diluted with water to a predetermined dose, and uniformly treated with a small spray on the foliage. Three weeks after the drug treatment, the influence on various plants was investigated according to the criteria of Test Example 1. The results are shown in Table 11.
[Test Example 4] Herbicidal effect test by soil treatment Put sterilized large soil in a plastic box 21cm long, 13cm wide and 7cm deep, and then weed bark, Enocorosa, Inobie, oats, blackgrass, Italian ryegrass, Atlantic cabbage, The seeds of Ichibi, Aogateto, Shiroza, Hakobe, Yaemugura, Ainu Fuuguri, Rice, Corn, Soybean, Wheat, Beet and Rapeseed were sown in spots and covered with about 1.5 cm of soil. Next, the emulsion of the compound of the present invention prepared according to Formulation Example 2 was diluted with water to a predetermined dose, and uniformly treated with a small spray on the soil surface. Plants were grown by placing plastic boxes in a greenhouse at 25 to 30 ° C., and after 3 weeks of chemical treatment, the effects on various plants were investigated according to the criteria of Test Example 1. The results are shown in Table 12.
[Test Example 5] Herbicidal effect test by foliar treatment Put sterilized piled soil in a plastic box 21cm long, 13cm wide, 7cm deep, and pearl bark, green croaker, barnyardgrass, oats, blackgrass, Italian ryegrass, yellow croaker, Spotted seeds of Ichibibi, Aogateto, Shiroza, Jacobe, Yamgra, Giant corn, rice, corn, soybean, wheat, beet, and rapeseed, covered with about 1.5 cm, and then planted in a greenhouse at 25 to 30 ° C. Nurtured. After growing for 14 days, the emulsion of the compound of the present invention prepared according to Formulation Example 2 was diluted with water to a predetermined dose, and uniformly treated with a small spray on the foliage. Three weeks after the drug treatment, the influence on various plants was investigated according to the criteria of Test Example 1. The results are shown in Table 13.

The symbols in Tables 9 to 13 represent the following meanings.
A: Nobies, B: Firefly, C: Konagi, D: Azegaya, E: Kogomegatsuri, F: Barbet, G: Enokirogusa, H: Inubie, I: Oats, J: Blackgrass, K: Italian ryegrass, L: Atlantic calyx , M: Ichibi, N: Blue-headed toe, O: Shiroza, P: Jacobe, Q: Yamgra, R: Giant corn, a: Transplanted rice, b: Direct sowing rice, c: Corn, d: Soy, e: Wheat, f: Beet , G: rapeseed The treatment dose (g / ha) represents that the concentration was adjusted so that the number of grams (g) described was processed when converted per hectare (1 ha). .
[Table 9]
―――――――――――――――――――――――――
No. Treatment dose A B C a
(G / ha)
―――――――――――――――――――――――――
1-001 320 5 5 4 3
1-003 320 4 3 3 0
1-004 320 5 5 5 3
1-005 320 4 5 4 4
1-006 320 3 3 3 2
1-007 320 4 5 4 3
1-008 320 3 4 4 1
1-009 320 5 5 5 2
1-011 320 5 5 5 5
1-012 320 5 4 4 2
1-013 320 5 5 4 4
1-014 320 5 5 4 1
1-015 320 5 4 4 2
1-016 320 5 5 4 2
1-017 320 5 5 4 4
1-018 320 5 5 5 4
1-019 320 0 3 2 3
1-020 320 5 5 5 4
1-021 320 5 5 5 1
1-022 320 5 5 4 4
1-023 320 5 5 5 4
1-024 320 5 5 5 5
1-025 320 5 5 5 5
1-026 320 5 5 5 4
1-027 320 5 5 5
1-028 320 5 5 5 5
1-029 320 5 5 5 4
1-030 320 5 4 4 4
1-031 320 0 3 2 0
2-001 320 4 3 3 1
2-002 320 4 4 4 0
2-003 320 5 5 4 0
2-004 320 4 5 4 0
2-005 320 4 5 4 0
2-006 320 3 4 4 3
2-007 320 1 1 0 1
2-009 320 0 4 3 0
2-010 320 5 4 4 2
2-012 320 1 1 0 1
2-013 320 5 4 4 5
2-014 320 5 5 4 3
2-015 320 0 1 1 0
2-016 320 3 4 4 0
2-017 320 3 3 4 3
2-018 320 5 5 3 0
2-019 320 4 5 4 1
2-020 320 4 4 3 1
2-021 320 4 4 4 1
2-022 320 0 3 3 0
2-023 320 5 5 4 3
2-024 320 4 5 4 3
2-025 320 5 5 5 3
2-026 320 0 2 3 3
2-027 320 5 4 4 4
2-028 320 5 5 4 2
2-029 320 3 4 4 1
2-030 320 5 5 4 3
2-031 320 2 3 3 0
2-033 320 4 5 5 4
2-034 320 4 4 4 4
2-035 128 4 4 3 3
2-036 320 5 5 5 5
2-037 320 5 5 4 4
2-038 320 5 5 5 4
2-039 320 5 5 5 4
2-040 320 0 1 2 0
2-041 320 3 3 4 0
2-042 320 2 3 3 1
2-043 320 1 2 1 0
2-044 320 5 5 4 3
2-045 320 3 1 2 0
2-046 320 4 4 4 3
2-047 320 1 3 2 5
2-048 320 4 4 4 5
2-049 320 4 4 4 3
2-050 320 4 3 2 1
2-051 320 4 4 4 4
2-052 320 0 1 0 0
3-001 320 5 4 4 4
3-002 320 4 5 4 4
3-003 320 4 4 3 4
3-004 320 5 5 5 4
3-005 320 5 5 5 4
3-006 320 4 4 4 4
3-007 320 4 3 3 3
3-008 320 3 3 4 3
3-009 320 0 3 4 4
3-010 320 5 5 5 4
3-012 320 5 4 4 5
3-013 320 5 5 5 4
3-014 320 3 3 4 2
3-015 320 5 5 5 4
3-016 320 4 5 4 4
3-017 320 3 4 4 3
3-018 320 5 5 5 4
3-019 320 4 5 5 5
3-020 320 5 5 5 3
3-021 320 5 5 4 4
3-022 320 3 4 4 5
3-023 320 5 4 5 4
3-024 320 5 5 5 4
3-025 320 4 4 4 3
3-026 320 5 5 5 5
3-027 320 5 5 5 5
3-028 320 2 4 4 3
3-029 320 2 3 4 1
―――――――――――――――――――――――――
[Table 10]
―――――――――――――――――――――――――
No. Treatment dose A B C
(G / ha)
―――――――――――――――――――――――――
1-001 320 4 5 4
1-003 320 3 4 4
1-004 320 4 5 4
1-005 320 4 4 5
1-006 320 3 2
1-007 320 4 4 4
1-008 320 1 3 3
1-009 320 5 5 4
1-011 320 5 5 5
1-012 320 4 4 2
1-013 320 3 4 3
1-014 320 5 5 4
1-015 320 4 3 4
1-016 320 4 3 3
1-017 320 5 4 4
1-018 320 5 5 4
1-019 320 2 4
1-020 320 5 3 5
1-021 320 5 5 4
1-022 320 4 5 5
1-023 320 4 5 4
1-024 320 5 5
1-025 320 4 5 4
1-026 320 5 5 5
1-027 320 5 5 5
1-028 320 5 5 5
1-029 320 5 4 4
1-030 320 4 4 4
1-031 320 0 1 1
2-001 320 4 2 2
2-002 320 5 4 4
2-003 320 4 3 3
2-004 320 3 4 4
2-005 320 4 4 3
2-006 320 5 5 4
2-007 320 3 1 0
2-008 320 2 3 2
2-009 320 3 3 3
2-010 320 4 5 4
2-012 320 0 1 0
2-013 320 5 4 4
2-014 320 4 5 3
2-016 320 3 3 2
2-017 320 3 3 3
2-018 320 3 3 4
2-019 320 3 4 4
2-020 320 4 3 3
2-021 320 3 3 4
2-022 320 3 2 3
2-023 320 4 4 4
2-024 320 4 4 4
2-025 320 3 4 4
2-026 320 3 3 4
2-027 320 4 4 5
2-028 320 4 4 3
2-029 320 1 3 4
2-030 320 4 4
2-031 320 0 2 3
2-033 320 4 4 4
2-034 320 4 4 4
2-035 128 3 4 4
2-036 320 4 5 4
2-037 320 5 4 5
2-038 320 5 5 4
2-039 320 5 4 4
2-040 320 0 1 0
2-041 320 3 3 3
2-042 320 0 2 3
2-043 320 1 3 3
2-044 320 5 4 5
2-045 320 3 2 3
2-046 320 2 4 4
2-047 320 3 3 3
2-048 320 2 4 4
2-049 320 4 4 4
2-050 320 2 3
2-051 320 4 3 4
3-001 320 5 4 3
3-002 320 4 5 5
3-003 320 4 5 4
3-004 320 3 5 5
3-005 320 3 5 5
3-006 320 4 5 4
3-007 320 2 3 4
3-008 320 3 4 3
3-009 320 3 3 4
3-010 320 3 5 4
3-012 320 3 4 4
3-013 320 3 4
3-014 320 3 4 4
3-015 320 4 5 4
3-016 320 4 5 4
3-017 320 4 4 4
3-018 320 4 5 4
3-019 320 5 4 4
3-020 320 5 5 5
3-021 320 4 5 4
3-022 320 4 4 4
3-023 320 5 5 5
3-024 320 4 5 5
3-025 320 3 4 5
3-026 320 5 5 5
3-027 320 5 5 4
3-028 320 3 3 4
3-029 320 2 2 4
―――――――――――――――――――――――――
[Table 11]
―――――――――――――――――――――――――
No. Treatment dose H D E b
(G / ha)
―――――――――――――――――――――――――
1-001 320 5 5 5 2
1-002 320 1 2 1 0
1-003 320 5 5 5 0
1-004 320 5 5 5 0
1-005 320 5 5 5 4
1-006 320 5 5 5 3
1-007 320 5 5 5 5
1-008 320 5 5 5 3
1-009 320 5 5 5 5
1-011 320 5 5 5 5
1-012 320 5 5 5 1
1-013 320 4 5 5 3
1-014 320 5 5 5 1
1-015 320 5 5 5 2
1-016 320 5 5 5 4
1-017 320 5 5 5 4
1-018 320 5 5 5 2
1-019 320 5 5 5 4
1-020 320 5 5 5 4
1-021 320 5 5 5 4
1-022 320 5 5 5 5
1-023 320 5 5 5 4
1-024 320 5 5 5 5
1-025 320 5 5 5 5
1-026 320 5 5 5 5
1-027 320 5 5 5 5
1-028 320 5 5 5 5
1-029 320 5 5 4 4
1-030 320 5 5 5 5
1-031 320 4 2 3 1
2-001 320 5 5 4 1
2-002 320 5 5 5 4
2-003 320 5 5 5 2
2-004 320 5 5 5 0
2-005 320 5 5 5 0
2-006 320 5 5 5 0
2-007 320 5 5 4 4
2-008 320 5 5 5 4
2-009 320 5 5 5 4
2-010 320 5 5 5 4
2-012 320 5 5 4 1
2-013 320 5 5 5 5
2-014 320 5 5 5 5
2-015 320 4 5 4 1
2-016 320 3 5 5 0
2-017 320 5 5 5 1
2-018 320 5 5 5 1
2-019 320 5 5 5 4
2-020 320 5 5 5 2
2-021 320 5 5 5 3
2-022 320 5 5 5 1
2-023 320 5 5 5 3
2-024 320 5 5 5 5
2-025 320 5 5 5 3
2-026 320 5 5 5 4
2-027 320 5 5 5 4
2-028 320 5 5 5 3
2-029 320 5 5 5 4
2-030 320 5 5 5 4
2-033 320 5 5 5 5
2-034 320 5 5 5 4
2-035 128 5 5 5 3
2-036 320 5 5 5 5
2-037 320 5 5 5 5
2-038 320 5 5 5 5
2-039 320 5 5 5 5
2-040 320 5 5 5 1
2-041 320 5 5 5 2
2-042 320 4 4 4 0
2-043 320 3 4 4 1
2-044 320 5 5 5 4
2-045 320 5 5 5 1
2-046 320 5 5 5 4
2-047 320 5 5 5 5
2-048 320 5 5 5 4
2-049 320 5 5 5 4
2-050 320 5 5 5 2
2-051 320 5 5 5 4
2-052 320 5 2 4 1
3-001 320 5 5 5 5
3-002 320 5 5 5 5
3-003 320 5 5 5 4
3-004 320 5 5 5 5
3-005 320 5 5 5 5
3-006 320 5 5 5 5
3-007 320 5 5 5 5
3-008 320 5 5 4 5
3-009 320 5 5 5 5
3-010 320 5 5 5 5
3-012 320 5 5 5 5
3-013 320 5 5 5 5
3-014 320 5 5 4 3
3-015 320 5 5 5 4
3-016 320 5 5 5 4
3-017 320 5 5 4 4
3-018 320 5 5 5 5
3-019 320 5 5
3-020 320 5 5 5 5
3-021 320 5 5 5 4
3-022 320 5 5 5 5
3-023 320 5 5 5 5
3-024 320 5 5 5 5
3-025 320 5 5 5 5
3-026 320 5 5 5 5
3-027 320 5 5 5 5
3-028 320 5 5 5 4
3-029 320 5 4 4 3
―――――――――――――――――――――――――
[Table 12]
―――――――――――――――――――――――――――――――――――――
No. Treatment dose FGHIJKLMNOPPQR b cd def g
(G / ha)
―――――――――――――――――――――――――――――――――――――
1-001 320 0 0 0 0 0 0 0 0 0 0 0 0 4
1-003 320 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0
1-004 320 5 1 1 0 0 0 0 2 3 2 3 1 0 0 0 0 0
1-005 320 3 1 0 0 0 0 3 0 0 4 4 0 0 0 0 3
1-006 320 1 0 0 0 0 0 0 0 3 0 0 0 0 1 0 0 0 0 0
1-008 320 1 0 0 0 0 0 0 1 1 0 0 0 0 0 0 0 0 0
1-009 320 5 0 0 0 0 0 4 0 0 0 0 0 0 0 0
1-011 320 5 4 4 0 0 0 0 3 3 4 5 5 2 0 0 0 0 0
1-013 320 5 0 0 0 0 0 0 0 0 5 0 0 0 0 0 0 5 0
1-014 320 5 4 3 0 0 0 5 1 4 0 0 0 0 0 0 0
1-015 320 4 0 0 0 0 0 0 0 0 3 0 0 0 0 0 0
1-016 320 5 1 0 0 0 0 0 0 0 0 3 0 5 0 0 0 0 5 0
1-017 320 2 0 0 0 0 1 1 3 3 0 0 0 0 0 0 5 0
1-018 320 5 3 0 0 0 0 0 3 3 0 0 0 0 0 0
1-019 320 1 0 0 0 0 0 2 1 0 0 0 0 0 0 0 0 0 0
1-020 320 4 0 0 0 0 0 0 0 1 3 0 0 2 0 0 0 0 0 0
1-022 320 0 0 0 0 0 0 0 0 0 5 4 5 0 0 0 0 5 0
1-023 320 5 0 0 0 0 0 0 4 3 0 0 0 0 0 0 0 0 0 0
1-024 320 2 3 0 0 0 0 0 2 3 0 0 0 3 0 0 0 0 0 0
1-025 320 5 3 0 0 0 0 4 0 0 5 3 5 4 0 0 0 0 0
1-026 320 4 3 0 0 0 0 0 0 4 0 0 0 0 0 0 0 0 0
1-027 320 5 5 0 0 0 0 4 5 5 5 0 4 0 0 0 0 5 0
1-028 320 5 5 4 0 0 0 0 4 4 4 2 0 0 0 0 0 0 3
1-029 320 5 1 4 0 0 0 0 5 4 0 0 0 0 0 0 0 0 0 0
1-031 320 0 0 0 0 0 0 0 0 0 5 0 0 0 0 0 0 0 0 0
2-001 320 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0
2-002 320 4 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
2-003 320 5 0 1 0 0 0 0 0 0 4 0 0 0 0 0 0 0 0 0
2-004 320 3 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0
2-005 320 3 0 0 0 0 0 0 5 0 0 0 0 0 0 0 0 0 0
2-007 320 0 0 0 0 0 0 0 0 2 0 0 0 0 0
2-008 320 0 0 0 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0
2-010 320 0 0 0 0 0 0 4 0 0 0 0 0 0 0 0 0 0 0 0
2-013 320 4 0 1 0 0 0 0 1 0 0 0 0 1 0 0 0 0
2-014 320 4 1 0 0 0 0 0 0 0 5 0 5 1 0 0 0 0 0
2-016 320 0 0 0 0 0 0 0 0 4 0 1 0 0 0 0 0 0
2-017 320 0 0 0 0 0 0 0 0 0 5 2 3 0 0 0 0 0 0
2-018 320 4 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0
2-019 320 4 3 0 0 0 3 5 1 3 4 4 5 4 0 0 0 0 0 2
2-022 320 0 0 0 0 0 0 0 0 0 0 0 5 0 0 0 0 5 0
2-023 320 5 0 0 0 0 0 5 0 0 0 0 0 0 0 5 0
2-024 320 0 0 1 0 0 0 0 0 0 5 0 0 0 0 0 0 0 0
2-026 320 5 0 0 0 0 0 3 0 5 5 3 3 0 0 0 0 4 0
2-027 320 2 0 0 0 0 0 0 0 0 5 0 0 0 0 0 0 0 0 0
2-028 320 3 0 0 0 0 0 3 0 0 0 0 0 0 0 0 0 0 0 0
2-030 320 5 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
2-033 320 1 0 0 0 0 0 0 0 0 5 0 0 0 0 0 0 0 0
2-034 320 4 3 0 0 0 0 0 3 0 0 0 0 0 0 0 0 0
2-036 320 5 0 0 0 0 0 0 0 0 5 0 0 2 0 0 0 0 0
2-037 320 3 0 3 0 0 0 0 4 3 4 2 0 0 0 0 0 0 0
2-038 320 5 3 0 0 0 3 2 4 0 0 0 0 0
2-039 320 3 0 0 0 0 0 1 1 0 0 0 0 0 0 0 0 0
2-040 320 0 0 0 0 0 0 0 0 0 2 0 2 0 0 0 0 0 0
2-044 320 4 0 1 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0
2-045 320 0 0 0 0 0 0 0 0 0 5 0 0 0 0 0 0 0 3 0
2-046 320 2 0 0 0 0 0 0 0 5 0 0 0 0 0 0 2 0
2-047 320 0 0 0 0 0 0 0 0 0 5 0 0 0 0 0 0 0 0
2-048 320 4 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
2-049 320 0 0 0 0 0 0 0 0 0 4 3 0 0 0 0 0 0 0
2-052 320 0 0 0 0 0 0 0 0 0 5 0 0 0 0 0 0 0 0 0
3-001 320 4 2 2 0 0 0 0 1 0 0 0 0
3-002 320 5 2 3 0 0 0 5 4 3 0 0 0 0 0 0 0
3-003 320 5 2 4 0 0 0 0 1 2 4 3 0 0 0 0 0 0 0
3-004 320 3 0 2 0 0 0 4 3 4 5 0 0 0 2 0 0
3-005 320 3 0 0 0 0 0 4 4 0 0 0 0 0 0 0 0
3-006 320 3 3 0 0 0 0 0 3 1 0 0 0 0 0 0
3-007 320 0 0 0 0 0 0 1 0 4 0 0 0 0 0 0 0 0 0
3-009 320 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0
3-010 320 4 0 0 0 0 0 4 0 0 0 0 0 0 0 0 0 0 0 0
3-012 320 2 0 2 0 0 0 2 0 2 0 0 0 0 0 0 0 0
3-013 320 4 4 3 0 0 0 0 0 0 0 3 2 0 0 0 0 0
3-015 320 3 0 0 0 0 0 0 0 0 4 0 0 0 0 5 0
3-016 320 0 0 0 0 0 0 4 0 0 5 4 0 0 1 0 0 0 3 0
3-017 320 3 0 0 0 0 0 0 0 0 5 4 3 0 0 0 0 0 0
3-018 320 5 4 4 0 0 0 5 1 5 5 0 0 3 3 0 0 0 0
3-019 320 0 1 0 1 1 0 0 5 5 4 5 1 0 0 0 5 0
3-020 320 0 3 5 0 0 0 0 3 0 5 4 0 0 2 0 0 0 5 0
3-021 320 2 0 0 0 0 0 0 0 3 0 0 0 0 0 5 0
3-022 320 3 0 0 0 0 0 1 1 5 2 0 3 0 0 0 0 5 1
3-023 320 5 0 0 0 0 2 3 4 0 4 0 0 0 1 0 0 0 0 5
3-024 320 1 0 1 0 0 0 5 0 0 0 0 0 0 0 0 0
3-025 320 0 0 0 0 0 0 0 0 0 5 5 0 3 0 0 0 0 0 0
3-026 320 3 4 0 0 0 0 3 0 0 0 0 0 0 5 3
3-027 320 5 0 0 0 4 0 5 4 0 5 0 4 0 0 1 0 5
3-028 320 3 0 0 0 0 0 0 1 3 0 0 0 0 0 0 0 0 0 0
―――――――――――――――――――――――――――――――――――――
[Table 13]
―――――――――――――――――――――――――――――――――――――
No. Treatment dose FGHIJKLMNOPPQR b cd def g
(G / ha)
―――――――――――――――――――――――――――――――――――――
1-001 320 5 5 5 4 3 3 4 4 5 5 5 4 5 0 0 5 4 5 5
1-002 320 2 0 2 0 0 0 0 3 3 0 0 0 0 2 0
1-003 320 5 5 5 4 3 2 4 3 4 5 4 3 4 1 1 4 3 5 4
1-004 320 4 5 5 4 1 2 4 5 5 5 5 4 5 0 2 5 2 5 5
1-005 320 5 4 5 4 4 4 5 4 5 5 5 5 5 4 0 5 4 5 5
1-006 320 5 4 5 2 1 1 4 5 5 5 5 3 5 2 1 5 2 5 5
1-007 320 5 5 5 3 1 3 3 5 5 5 4 3 5 4 5 5 3 5 5
1-008 320 4 3 5 2 2 1 2 5 5 5 5 2 0 5 3 4 3
1-009 320 5 5 5 3 3 3 4 5 5 5 5 5 3 4 5 4 5 5
1-011 320 5 5 5 4 3 4 5 5 5 5 5 5 5 5 1 5 4 5 5
1-012 320 5 5 4 0 0 0 0 4 5 5 5 0 5 0 0 3 0 5 4
1-013 320 5 4 5 2 1 1 4 5 5 5 5 0 5 1 0 3 2 5 5
1-014 320 5 5 5 5 4 5 5 5 5 1 4 5 4 5 5
1-015 320 5 4 4 3 3 3 4 4 4 5 1 1 2 4 3 5 5
1-016 320 5 5 5 3 2 2 3 5 5 5 5 4 5 1 1 5 2 5 5
1-017 320 4 3 4 5 5 5 5 5 4 5 5
1-018 320 5 3 5 4 5 5 4 4 5 1 1 4 4 5 5
1-019 320 5 4 5 3 2 2 4 5 4 5 5 1 5 4 0 3 3 5 5
1-020 320 5 4 5 5 4 3 5 4 5 5 4 5 3 3 5 4 5 5
1-021 320 5 5 5 5 3 3 5 5 5 5 5 3 5 1 5 5 1 5 5
1-022 320 5 5 5 4 3 3 4 5 5 5 5 5 5 5 4 4 1 5 5
1-023 320 5 5 5 3 3 3 4 4 4 5 5 3 2 0 5 2 5 5
1-024 320 5 5 5 5 4 4 5 5 5 5 5 5 5 3 5 5 5 5
1-025 320 5 5 5 4 3 4 5 5 5 5 5 0 5 5 3 5 4 5 5
1-026 320 5 5 5 4 3 4 5 5 2 5 4 3 5 4 2 5 4 5 5
1-027 320 5 5 5 5 4 4 5 5 5 5 5 5 5 4 5 5 5 5 5
1-028 320 5 5 5 5 4 4 5 5 4 5 4 4 4 4 5 5 5 5
1-029 320 5 4 5 3 3 3 4 4 0 5 4 3 2 0 4 1 5 4
1-030 320 5 5 5 4 3 3 3 4 4 4 3 4 0 5 3 5 5
1-031 320 1 0 2 0 2 2 4 5 4 4 3 1 0 2 0 5 4
2-001 320 5 5 5 5 3 3 4 4 4 5 5 4 5 1 2 5 3 5 5
2-002 320 5 5 5 5 4 3 5 5 5 5 3 4 5 3 5 5
2-003 320 5 5 5 4 3 3 4 5 5 4 4 4 4 1 3 4 2 5 4
2-004 320 5 4 5 2 2 2 4 5 5 5 4 4 0 3 3 1 4 3
2-005 320 5 5 5 3 3 3 4 5 5 5 5 5 0 1 4 2 5 5
2-006 320 5 5 5 4 3 3 4 4 5 5 5 4 5 4 0 3 4 5 4
2-007 320 5 5 5 3 2 1 4 5 5 5 4 0 2 0 5 3 5 5
2-008 320 5 5 5 3 3 2 3 5 5 5 4 0 4 4 5 5 3 5 4
2-009 320 5 3 5 3 3 2 3 4 4 5 4 3 4 4 1 4 3 5 4
2-010 320 5 5 5 1 3 3 4 5 5 5 5 5 3 4 5 3 5 5
2-012 320 5 4 5 3 2 2 2 4 4 5 4 4 4 3 0 3 3 5 4
2-013 320 5 5 5 4 4 4 3 5 5 5 4 4 5 5 5 4 4 5 5
2-014 320 5 5 5 3 3 4 4 5 5 5 5 4 5 5 0 5 3 5 5
2-015 320 5 1 5 2 2 0 3 5 2 5 4 3 5 0 0 4 0 5 5
2-016 320 5 3 4 0 3 3 4 4 3 5 5 3 4 0 0 1 0 5 4
2-017 320 5 4 4 1 0 0 4 5 5 5 5 2 5 0 3 3 0 5 5
2-018 320 5 4 5 2 2 3 5 4 3 5 4 1 1 4 2 5 4
2-019 320 5 5 5 2 3 3 5 5 5 5 5 3 5 1 5 1 2 5 5
2-020 320 5 4 5 3 3 2 4 4 5 5 4 0 1 4 4 5 5
2-021 320 5 4 5 2 2 3 3 4 5 5 5 4 0 1 4 0 5 4
2-022 320 5 5 5 3 3 3 3 4 4 5 5 3 5 3 1 4 3 5 5
2-023 320 5 5 5 4 3 4 5 4 1 5 5 4 5 1 1 4 3 5 4
2-024 320 5 4 5 3 4 3 5 5 3 5 5 4 5 3 2 4 5 5 5
2-025 320 5 5 5 3 4 3 5 4 4 5 4 2 1 4 3 5 4
2-026 320 5 5 5 2 3 3 3 4 4 5 5 5 5 4 0 4 3 5 5
2-027 320 5 4 5 4 3 3 3 3 3 5 4 3 4 4 1 4 3 5 4
2-028 320 5 5 5 4 3 4 5 5 5 5 5 3 5 0 5 4 1 5 5
2-029 320 5 5 5 3 3 3 4 4 4 5 5 3 4 1 1 3 3 5 5
2-030 320 5 4 5 2 3 3 4 4 4 5 4 3 1 0 4 1 5 4
2-031 320 4 0 1 0 0 0 0 1 2 5 2 2 3 0 1 3 0 5 3
2-033 320 5 5 5 5 4 4 5 5 5 5 4 3 3 3 5 5 5 5
2-034 320 5 5 5 5 5 5 4 0 5 4 4 5 4 2 2 5 5 5 5
2-035 128 5 5 5 3 4 3 5 4 4 4 3 3 4 4 4 4 4
2-036 320 5 5 5 3 4 4 5 5 5 5 5 5 5 5 5 3 5 5
2-037 320 5 5 5 5 4 4 5 4 3 5 4 4 4 3 5 3 5 5
2-038 320 5 5 5 5 5 5 5 5 5 5 5 4 5 5 5 5
2-039 320 5 5 5 5 4 3 5 5 4 5 5 5 4 4 5 3 5 5
2-040 320 5 4 4 2 0 0 4 5 1 5 3 3 3 2 0 2 0 5 2
2-041 320 5 5 5 2 3 2 5 4 5 4 0 3 2 0 4 2 5 4
2-042 320 5 3 5 3 3 3 3 3 4 5 4 3 3 1 3 2 5 4
2-043 320 5 0 3 0 0 0 0 1 0 5 1 1 0 0 1 0 3 4
2-044 320 5 5 5 5 4 4 5 5 5 5 5 4 5 3 1 5 4 5 5
2-045 320 4 3 3 3 5 5 5 5 3 5 5
2-046 320 5 5 5 4 4 4 5 4 0 5 4 4 5 4 1 4 3 5 5
2-047 320 5 5 5 2 3 3 4 4 5 5 5 4 4 3 1 4 3 5 4
2-048 320 5 5 5 5 4 4 5 4 1 5 5 4 5 4 0 3 4 5 5
2-049 320 5 5 5 3 3 3 4 4 5 5 5 0 5 3 2 4 3 5 5
2-050 320 5 5 5 3 3 3 5 5 5 5 1 1 2 3 5 5
2-051 320 5 5 5 3 2 3 3 5 4 5 4 4 2 3 3 5 5
2-052 320 4 2 4 0 0 0 0 1 0 5 1 0 3 0 0 2 0 4 2
3-001 320 5 5 5 5 4 4 5 5 4 5 5 5 5 5 4 5 5 5 5
3-002 320 5 5 5 2 4 4 5 5 5 5 5 5 4 5 5 5 5
3-003 320 5 5 5 4 4 4 4 5 5 5 4 3 4 5 2 4 4 4 4
3-004 320 5 5 5 4 4 3 5 5 5 5 5 4 5 5 3 5 4 5 5
3-005 320 5 5 5 5 4 4 5 5 5 5 5 5 4 5 4 4 5 5
3-006 320 5 5 5 4 5 4 5 5 5 5 5 4 5 4 1 5 5 5 5
3-007 320 5 5 5 5 4 3 5 5 5 5 4 3 5 5 3 5 4 5 5
3-008 320 5 5 5 3 3 3 3 5 4 5 4 2 5 3 5 3 5 5
3-009 320 4 3 5 2 4 3 3 5 5 4 3 3 4 5 1 4 4 3 3
3-010 320 5 5 5 2 4 4 5 5 5 5 5 5 5 2 5 4 5 4
3-012 320 5 5 5 4 4 4 5 5 5 5 5 5 5 4 5 4 5 5
3-013 320 5 5 5 4 2 4 3 5 5 5 5 4 5 5 5 5 5 5 5
3-014 320 5 4 5 4 4 3 4 5 4 5 4 3 5 4 1 5 3 5 5
3-015 320 5 5 5 3 4 4 3 5 5 5 5 5 4 0 4 3 5 5
3-016 320 5 4 5 5 4 3 3 5 5 5 5 5 5 5 1 3 4 5 5
3-017 320 5 4 5 4 4 3 4 4 3 5 3 3 2 4 3 5 5
3-018 320 5 5 5 4 3 3 5 5 5 5 5 5 5 4 5 3 5 4
3-019 320 5 5 5 5 5 4 5 5 4 5 5 5 5 5 3 4 4 5 5
3-020 320 5 1 5 4 4 4 5 5 5 5 5 4 5 5 3 4 3 5 5
3-021 320 4 3 4 3 5 4 4 4 5 3 3 1 5 4 5 5
3-022 320 5 5 5 4 4 4 3 4 3 5 5 5 5 4 1 4 4 5 5
3-023 320 5 5 5 5 5 5 5 5 5 5 5 4 3 1 5 5 5 5
3-024 320 5 5 5 5 5 5 5 5 5 5 5 5 5 5 4 5 5 5
3-025 320 5 4 5 5 5 4 4 5 5 5 5 4 5 5 4 5 5 5 3
3-026 320 5 5 5 5 4 5 5 5 0 5 4 4 5 5 4 4 5 5 5
3-027 320 5 5 5 5 5 5 5 5 5 5 5 4 5 5 4 5 5 5 5
3-028 320 5 5 5 4 3 3 4 5 2 5 4 3 5 2 0 4 3 5 5
3-029 320 5 4 4 3 0 2 4 4 5 5 5 4 1 1 3 0 5 3
―――――――――――――――――――――――――――――――――――――

  The heterocyclic amide compound of the present invention is a novel compound and is useful as a selective herbicide for rice, corn, soybean, wheat, beet and rapeseed.

Claims (4)

Formula (1):

[Wherein Q represents an aromatic heterocycle represented by any one of Q-1 to Q-7,

W represents an aromatic heterocyclic ring represented by W-1,

X represents an oxygen atom or a sulfur atom,
R ^1a represents (C ₁ -C ₆ ) alkyl, —S (O) _m1 R ¹⁴ , V-1, V-2, V-3, V-4 or V-5, optionally substituted with R ⁶ . Represent,
V-1 to V-5 each represent a substituent represented by the following structure,

R ^2a represents a halogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, —C (O) R ²⁵ , cyano, nitro, —OR ²⁶ or —S (O) _m5 R ²⁷ , and n is When each represents an integer of 2 or more, each R ^2a may be the same as or different from each other;
Further, when two R ^2a are adjacent, the two adjacent R ^2a are —CH ₂ CH ₂ CH ₂ —, —CH ₂ CH ₂ O—, —CH ₂ OCH ₂ —, —OCH ₂ O—, _{-CH 2 CH 2 S -, -} CH 2 SCH 2 -, - CH 2 CH 2 CH 2 CH 2 -, - CH 2 CH 2 CH 2 O -, - CH 2 CH 2 OCH 2 -, - CH 2 OCH 2 Each of the two R ^2a is formed by forming O—, —OCH ₂ CH ₂ O—, —CH ₂ CH ₂ CH ₂ S—, —OCH ₂ CH ₂ S— or —CH═CH—CH═CH—. A 5-membered ring or a 6-membered ring may be formed together with the carbon atom to which is bonded, and at this time, the hydrogen atom bonded to each carbon atom forming the ring is a halogen atom, a C ₁ -C ₆ alkyl group or C _1. arbitrarily by ~C ₆ haloalkyl group It may have been conversion,
R ³ is a hydrogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₃ -C ₆ cycloalkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl or -C (O) R ²⁹ Represents
R ^4a , R ^4b , R ^4c , R ^4d , R ^4e , R ^4f , R ^4g and R ^4h are each independently optionally substituted with a hydrogen atom, a halogen atom, C ₁ -C ₆ alkyl, or R ³¹ . _(C 1 _{~C 6)} represents _alkyl, C 3 -C ₆ cycloalkyl, phenyl substituted by phenyl or ^(R _{32) q2,}
R ^5a , R ^5b and R ^5c are each independently substituted with a hydrogen atom, C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl, phenyl or (R ³² ) _q2 optionally substituted with R ³¹ Represented phenyl,
R ^{6 _{is, -N (R 7) R 8}} , -S (O) 2 N (R 7) R 8, U-1, U-2, U-3, U-4, U-5, U-6 Or U-7,
U-1 to U-7 each represent a heterocyclic ring or a substituent represented by the following structure,

R ⁷ represents —C (O) R ¹⁰ , —C (S) R ¹⁰ or —S (O) ₂ R ¹⁰ ,
R ⁸ is a hydrogen atom, C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl optionally substituted by R ¹⁵ , C ₃ -C ₆ cycloalkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ represents alkynyl, phenyl or —OR ¹⁷
R ⁹ represents a halogen atom, C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl, and when p 4, p 6 or p 8 represents an integer of 2 or more, each R ⁹ may be the same or mutually They may be different,
R ¹⁰ is a hydrogen atom, C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl optionally substituted by R ¹⁹ , C ₃ -C ₆ cycloalkyl, C ₂ -C ₆ alkenyl, C ₂ -C _{6 represents} alkynyl, —OR ¹¹ or —N (R ¹² ) R ¹³ ;
R ¹¹ represents a hydrogen atom, C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl,
R ¹² and R ¹³ each independently represent a hydrogen atom, C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl, or R ¹² together with R ¹³ is a C ₂ -C ₆ alkylene chain. Represents that a 3- to 7-membered ring may be formed together with the nitrogen atom to which R ¹² and R ¹³ are bonded, and this alkylene chain contains one oxygen atom, sulfur atom or nitrogen atom. But often, and halogen _atom, C 1 -C ₆ alkyl _group, C 1 -C ₆ haloalkyl _group, C 1 -C ₆ alkoxy group, a formyl _group, C 1 -C ₆ alkylcarbonyl _group, C 1 -C ₆ alkoxycarbonyl Optionally substituted by a group, an oxo group or a thioxo group,
R ¹⁴ represents (C ₁ -C ₆ ) alkyl optionally substituted with R ⁶ ;
R ¹⁵ represents a halogen atom, cyano or —OR ¹⁶ ,
R ¹⁶ and R ¹⁷ each independently represent a hydrogen atom, C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl,
R ¹⁸ represents C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl,
R ¹⁹ represents a halogen atom or —S (O) _m2 R ²⁰ ,
R ²⁰ , R ²¹ and R ²² each independently represent C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl,
R ²⁵ represents a hydrogen _atom, C 1 -C _{6 alkyl,} C 1 -C ₆ haloalkyl or ^{-OR 28,}
R ²⁶ represents a hydrogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl or phenyl;
R ²⁷ represents C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl,
R ²⁸ represents a hydrogen atom, C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl,
R ²⁹ represents a hydrogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl or —OR ³⁰ ;
R ³⁰ represents a hydrogen atom, C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl,
R ³¹ represents a halogen atom, phenyl, —OR ³³ or —S (O) _m6 R ³⁴ ,
R ³² represents a halogen atom, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl or —OR ^35, and when q 2 represents an integer of 2 or more, each R ³² may be the same as each other or They may be different,
Furthermore, when two R ³² are adjacent, two adjacent R ³² are —CH ₂ CH ₂ CH ₂ —, —CH ₂ CH ₂ O—, —CH ₂ OCH ₂ —, —OCH ₂ O—, _{-CH 2 CH 2 S -, -} CH 2 SCH 2 -, - CH 2 CH 2 CH 2 CH 2 -, - CH 2 CH 2 CH 2 O -, - CH 2 CH 2 OCH 2 -, - CH 2 OCH 2 _{O -, - OCH 2 CH 2} O -, - CH 2 CH 2 CH 2 S -, - OCH by 2 _CH 2 S- or forming a -CH = CH-CH = CH-, each of the two ^{R 32} A 5-membered ring or a 6-membered ring may be formed together with the carbon atom to which is bonded, and at this time, the hydrogen atom bonded to each carbon atom forming the ring is a halogen atom, a C ₁ -C ₆ alkyl group or C _1. arbitrarily by ~C ₆ haloalkyl group It may have been conversion,
R ³³ represents a hydrogen atom, C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl,
R ³⁴ represents C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl,
R ³⁵ represents a hydrogen atom, C ₁ -C ₆ alkyl or C ₁ -C ₆ haloalkyl,
m1, m5 and m6 each independently represents an integer of 0, 1 or 2;
n independently represents an integer of 0, 1, 2, or 3,
p4 represents an integer of 0, 1, 2, 3 or 4;
p6 represents an integer of 0, 1, 2, 3, 4, 5 or 6,
p8 represents an integer of 0, 1, 2, 3, 4, 5, 6, 7 or 8;
q2 represents an integer of 1, 2, 3, 4 or 5. Or a salt thereof. Q represents Q-1 or Q-3,
X represents an oxygen atom,
R ^1a represents (C ₁ -C ₆ ) alkyl, —S (O) _m1 R ¹⁴ or V-1, optionally substituted with R ⁶ ,
R ^2a represents C ₁ -C ₆ haloalkyl,
R ³ represents a hydrogen atom,
R ^4a represents a hydrogen atom or C ₁ -C ₆ alkyl;
R ^5a represents C ₁ -C ₆ alkyl;
R ⁶ represents —N (R ⁷ ) R ⁸ , U-1, U-3, U-4, U-6 or U-7,
R ⁸ is a hydrogen atom, C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl, C ₃ -C ₆ cycloalkyl, C ₂ -C ₆ alkynyl, phenyl or —OR optionally substituted by R ¹⁵ . ¹⁷
R ¹⁰ represents C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl, C ₃ -C ₆ cycloalkyl, —OR ¹¹ or —N ¹¹ or —N (R ¹² ) R ¹³ optionally substituted by R ¹⁹ . ,
R ¹¹ represents C ₁ -C ₆ alkyl,
R ¹² and R ¹³ each independently represent a hydrogen atom or C ₁ -C ₆ alkyl;
R ¹⁶ , R ¹⁷ , R ¹⁸ , R ²⁰ , R ²¹ and R ²² each independently represent C ₁ -C ₆ alkyl;
m1 represents an integer of 0;
n represents an integer of 1;
p4, p6, and p8 represent an integer of 0. The heterocyclic amide compound of Claim 1 represented by this, or its salt.   An agrochemical containing one or more selected from the heterocyclic amide compounds according to claim 1 and a salt thereof as active ingredients.   The herbicide which contains 1 type, or 2 or more types chosen from the heterocyclic amide compound and its salt of Claim 1-2 as an active ingredient.