JP2021006524A - Heterocyclic compound - Google Patents

Abstract

To provide novel agrochemicals, particularly a herbicide.SOLUTION: There are provided heterocyclic compounds represented by a formula (1), [where, Q indicates Q-1, Q-2, or Q-3; R1 indicates a hydrogen atom, a halogen atom, a C1-C6 alkyl, or the like; R2 indicates a halogen atom, a C1-C6 alkyl, or the like; R3 indicates a C1-C6 alkyl, a C3-C6 cycloalkyl (C1-C6) alkyl, or the like; and R4 indicates a hydrogen atom or a C1-C6 alkyl], and a herbicide containing the compounds.SELECTED DRAWING: None

Description

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

For example, Patent Documents 1 to 4 disclose certain heterocyclic compounds, but do not disclose any heterocyclic compounds according to the present invention.

International Publication No. 2014/126070 International Publication No. 2017/005564 International Publication No. 2017/005567 International Publication No. 2017/05/51446

An object of the present invention is a highly safe active ingredient of a herbicide, which is surely effective against various weeds with a lower drug amount and alleviates problems such as soil contamination and effects on post-crops. Is to provide useful chemicals.

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

［式中、Ｑは、Ｑ−１、Ｑ−２又はＱ−３の何れかで表される環を表し、

That is, the present invention relates to the following [1] to [9].
[1]
Equation (1):

[In the formula, Q represents a ring represented by any of Q-1, Q-2 or Q-3.

R ¹ is hydrogen atom, halogen _atom, C 1 -C ₆ ^alkyl, substituted in ^{R 1a} _(C 1 ~C _{6) alkyl,} C 1 -C _{6 alkylthio,} C 1 -C _{6 alkylsulfinyl, C} 1 ~ Represents C ₆ alkyl sulfonyl, C _{3 to} C ₆ cycloalkyl or (C _{1 to} C ₆ ) cycloalkyl substituted with R ^1b .
R ^1a represents a halogen atom, cyano, C _{3 to} C ₆ cycloalkyl, C _{1 to} C ₆ alkylthio, C _{1 to} C ₆ alkyl sulfinyl or C _{1 to} C ₆ alkyl sulfonyl.
R ^1b represents a halogen atom and represents
R ² represents a hydrogen atom, a halogen atom, a C _{1 to} C ₆ alkyl or a halo (C _{1 to} C ₆ ) alkyl.
R ³ is C _{1 to} C ₆ alkyl, C _{3 to} C ₆ cycloalkyl, C _{3 to} C ₆ cycloalkyl (C _{1 to} C ₆ ) alkyl, halo (C _{1 to} C ₆ ) alkyl, C _{2 to} C ₆ Alkenyl, halo (C _{2 to} C ₆ ) alkenyl, C _{2 to} C ₆ alkynyl, halo (C _{2 to} C ₆ ) alkynyl, (C _{1 to} C ₆ ) alkyl substituted with R ^3a , -C (O) R ¹⁰ , -C (O) OR ¹¹ , -C (O) SR ¹² , -C (O) N (R ¹³ ) R ¹⁴ , -C (S) OR ¹⁶ , -C (S) SR ¹⁷ , -S ( _O) 2 ^{R 18,} pyridin-2-yl, represents a 5-chloropyridin-2-yl or 5-trifluoromethyl-2-yl,
R ^3a is -OR ²¹ , -OC (O) R ²² , -OC (O) OR ²³ , -S (O) nR ²⁴ , -C (O) R ²⁵ , -C (O) OR ²⁶ , -C. Represents (O) SR ²⁷ , -C (O) N (R ²⁸ ) R ²⁹ , -N (R ³⁰ ) R ³¹ , cyano, nitro, naphthyl or G1.
R ⁴ represents a hydrogen atom or C _{1 to} C ₆ alkyl.
R ¹⁰ is C _{1 to} C ₆ alkyl, C _{3 to} C ₆ cycloalkyl, C _{3 to} C ₆ cycloalkyl (C _{1 to} C ₆ ) alkyl, halo (C _{1 to} C ₆ ) alkyl, C _{2 to} C _{6 alkenyl,} C 2 -C ₆ ^alkynyl, substituted in ^{R 10a} _(C 1 ~C ₆₎ alkyl or G1,
R ^10a contains C _{1 to} C ₆ alkoxy, C _{1 to} C ₆ alkylthio, C _{1 to} C ₆ alkyl sulfinyl, C _{1 to} C ₆ alkyl sulfonyl, C _{1 to} C ₆ alkyl carbonyl, phenoxy, cyano, nitro or G1. Represent,
R ¹¹ is C _{1 to} C ₆ alkyl, C _{3 to} C ₆ cycloalkyl, C _{3 to} C ₆ cycloalkyl (C _{1 to} C ₆ ) alkyl, halo (C _{1 to} C ₆ ) alkyl, C _{2 to} C _{6 alkenyl,} C 2 -C ₆ ^alkynyl, substituted in ^{R 11a} _(C 1 ~C ₆₎ alkyl or G1,
R ^11a represents C _{1 to} C ₆ alkoxy, tetrahydrofuran-2-yl or G1.
R ¹² represents C _{1 to} C ₆ alkyl or (C _{1 to} C ₆ ) alkyl substituted with R ^12a .
R ^12a represents C _{1 to} C ₆ alkoxycarbonyl or G1.
R ¹³ and R ¹⁴ are independently hydrogen atoms, C _{1 to} C ₆ alkyl, halo (C _{1 to} C ₆ ) alkyl, C _{1 to} C ₆ alkoxy (C _{1 to} C ₆ ) alkyl, and C _{2 to} C, respectively. _{6 alkenyl,} or represents C 2 -C ₆ alkynyl or phenyl, ^{or by R 13} to form a _C 2 -C ₆ alkylene chain together with ^{R 14,} the nitrogen atom ^{to which R 13} and ^{R 14} are bonded At this time, the alkylene chain may contain one O, S, S (O), S (O) ₂ or N (R ¹⁵ ).
R ¹⁵ represents C _{1 to} C ₆ alkyl and represents
R ¹⁶ and R ¹⁷ represent phenyl
R ¹⁸ represents C _{1 to} C ₆ alkyl, halo (C _{1 to} C ₆ ) alkyl, -N (R ¹⁹ ) R ²⁰ , R ^18a substituted (C _{1 to} C ₆ ) alkyl or G1.
R ^18a represents C _{1 to} C ₆ alkoxy or G1.
R ¹⁹ and R ²⁰ independently represent C _{1 to} C ₆ alkyl or phenyl, respectively.
R ²¹ , R ²² , R ²⁴ and R ²⁵ are independently C _{1 to} C ₆ alkyl, halo (C _{1 to} C ₆ ) alkyl, C _{1 to} C ₆ alkoxy (C _{1 to} C ₆ ) alkyl or G1 respectively. Represents
R ²³ represents C _{1 to} C ₆ alkyl or C _{3 to} C ₆ cycloalkyl.
R ²⁶ , R ²⁷ , R ²⁸ , R ²⁹ , R ³⁰ , R ³¹ , R ³³ , R ³⁴ , R ³⁵ , R ³⁶ , R ³⁷ and R ³⁸ each independently represent C _{1 to} C ₆ alkyl.
R ³² represents C _{1 to} C ₆ alkyl, halo (C _{1 to} C ₆ ) alkyl, C _{1 to} C ₆ alkyl carbonyl, C _{1 to} C ₆ alkoxycarbonyl or C _{1 to} C ₆ alkyl sulfonyl.
G1 represents a ring represented by any of G1-1 to G1-31.

Z ₁ is a halogen atom, C _{1 to} C ₆ alkyl, halo (C _{1 to} C ₆ ) alkyl, C _{2 to} C ₆ alkenyl, halo (C _{2 to} C ₆ ) alkenyl, C _{2 to} C ₆ alkynyl, halo ( C _{2 to} C ₆ ) alkynyl, C _{1 to} C ₆ alkoxy, halo (C _{1 to} C ₆ ) alkoxy, C _{1 to} C ₆ alkylthio, halo (C _{1 to} C ₆ ) alkyl thio, C _{1 to} C ₆ alkyl sulfinyl, Halo (C _{1 to} C ₆ ) alkyl sulfinyl, C _{1 to} C ₆ alkyl sulfonyl, halo (C _{1 to} C ₆ ) alkyl sulfonyl, C _{1 to} C ₆ alkoxy (C _{1 to} C ₆ ) alkyl, halo (C ₁ to C ₆ ) C ₆ ) Alkoxy (C _{1 to} C ₆ ) alkyl, C _{1 to} C ₆ alkyl thio (C _{1 to} C ₆ ) alkyl, halo (C _{1 to} C ₆ ) alkyl thio (C _{1 to} C ₆ ) alkyl, C _{1 to} C ₆ Alkyl sulfinyl (C _{1 to} C ₆ ) alkyl, halo (C _{1 to} C ₆ ) alkyl sulfinyl (C _{1 to} C ₆ ) alkyl, C _{1 to} C ₆ alkyl sulfonyl (C _{1 to} C ₆ ) alkyl, halo (C) ₁ ~
C ₆ ) Alkoxysulfonyl (C _{1 to} C ₆ ) alkyl, C _{1 to} C ₆ alkoxy (C _{1 to} C ₆ ) alkoxy, cyano (C _{1 to} C ₆ ) alkyl, C _{1 to} C ₆ alkyl carbonyl, C ₁ to C ₆ Alkoxycarbonyl, -CHO, -NHR ³² , -N (R ³³ ) R ³⁴ , -C (O) OH, -C (O) NH ₂ , -C (O) N (R ³⁵ ) R ³⁶ ,- ^{_{S (O) 2 N (R}} 37) R 38, hydroxy, -NH _2, cyano or nitro, p2, p3, if p4 or p5 represents an integer of 2 or more, each _{Z 1} is each independently a be different even or different from each other well by further, if two of _{Z 1} are adjacent, the two adjacent _{Z 1} is -CH = CH-CH = CH - , - NH-CH = CH- , -S-CH = CH-, -O-CH = CH- or -OCH ₂ O- to form a 5- or 6-membered ring with the carbon atom to which each Z ₁ is bonded. Often,
T ₁ represents a hydrogen atom, C _{1 to} C ₆ alkyl or halo (C _{1 to} C ₆ ) alkyl.
p1 represents an integer of 0 or 1,
p2 represents an integer of 0, 1 or 2,
p3 represents an integer of 0, 1, 2 or 3
p4 represents an integer of 0, 1, 2, 3 or 4
p5 represents an integer of 0, 1, 2, 3, 4 or 5
n represents an integer of 0, 1 or 2. ] Represented by a heterocyclic compound or a salt thereof.

[2]
R ¹ is C _{1 to} C ₆ alkyl, R ¹ a substituted (C _{1 to} C ₆ ) alkyl, C _{1 to} C ₆ alkyl thio, C _{1 to} C ₆ alkyl sulfinyl, C _{1 to} C ₆ alkyl sulfonyl or R. ^Represents a (C _1- C ₆ ) cycloalkyl substituted with ^1b .
R ^1a represents C _{1 to} C ₆ alkylthio, C _{1 to} C ₆ alkyl sulfinyl or C _{1 to} C ₆ alkyl sulfonyl.
R ² represents halo (C _{1 to} C ₆ ) alkyl and represents
R ³ was replaced with C _{1 to} C ₆ alkyl, C _{3 to} C ₆ cycloalkyl (C _{1 to} C ₆ ) alkyl, C _{2 to} C ₆ alkenyl, C _{2 to} C ₆ alkynyl, and R ^3a (C _1). ~ C ₆ ) Alkyne, -C (O) R ¹⁰ , -C (O) OR ¹¹ , -C (O) N (R ¹³ ) R ¹⁴ or -S (O) ₂ R ¹⁸
R ^3a represents -OR ²¹ , -OC (O) OR ²³ , cyano or G1.
R ¹⁰ represents C _{1 to} C ₆ alkyl or G1
R ¹¹ represents C _{1 to} C ₆ alkyl and represents
R ¹³ and R ¹⁴ each independently represent C _{1 to} C ₆ alkyl, or R ¹³ can be combined with R ¹⁴ to form a C _{2 to} C ₆ alkylene chain, thereby forming R ¹³ and R. ^{It represents that 14} forms a 3- to 7-membered ring with the nitrogen atom to which it binds, even if the alkylene chain contains one O, S, S (O), S (O) ₂ or N (R ¹⁵ ) Often,
R ¹⁸ represents C _{1 to} C ₆ alkyl, -N (R ¹⁹ ) R ²⁰ or G1.
R ¹⁹ and R ²⁰ independently represent C _{1 to} C ₆ alkyl, respectively.
R ²¹ is the heterocyclic compound or a salt thereof according to the above [1], which represents C _{1 to} C ₆ alkyl.

[3]
Q is the heterocyclic compound or salt thereof according to the above [2], which represents the ring represented by Q-1.

[4]
Q is the heterocyclic compound or salt thereof according to the above [2], which represents the ring represented by Q-2.

[5]
Q is the heterocyclic compound or salt thereof according to the above [2], which represents the ring represented by Q-3.

[6]
R ³ is C _{1 to} C ₆ alkyl, C _{3 to} C ₆ cycloalkyl (C _{1 to} C ₆ ) alkyl, C _{2 to} C ₆ alkenyl, (C _{1 to} C ₆ ) alkyl substituted with R ^3a or- Represents C (O) OR ¹¹
R ^3a represents -OR ²¹ , -OC (O) OR ²³ or G1.
R ²³ represents C _{1 to} C ₆ alkyl and represents
G1 represents G1-1 or G1-3
Z ₁ represents a halogen atom
p4 represents an integer of 1 and represents
p5 is the heterocyclic compound or salt thereof according to the above [3], which represents an integer of 0.

[7]
R ³ is C _{1 to} C ₆ alkyl, C _{3 to} C ₆ cycloalkyl (C _{1 to} C ₆ ) alkyl, C _{2 to} C ₆ alkenyl, (C _{1 to} C ₆ ) alkyl substituted with R ^3a or- Represents C (O) OR ¹¹
R ^3a represents -OR ²¹ , -OC (O) OR ²³ or G1.
R ²³ represents C _{1 to} C ₆ alkyl and represents
G1 represents G1-1 or G1-3
Z ₁ represents a halogen atom
p4 represents an integer of 1 and represents
p5 is the heterocyclic compound or salt thereof according to the above [4], which represents an integer of 0.

[8]
A pesticide containing one or more selected from the heterocyclic amide compounds and salts thereof according to the above [1] to [7] as an active ingredient.

[9]
A herbicide containing one or more selected from the heterocyclic amide compounds and salts thereof according to the above [1] to [7] as active ingredients.

The compound of the present invention has excellent herbicidal activity against various weeds and has high safety against target crops. Furthermore, it has almost no adverse effect on non-target organisms such as mammals, fish and beneficial insects, has low persistence, and has a light environmental load.
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 E-form and Z-form geometric isomers depending on the type of the substituent, but the present invention presents these E-form, Z-form or E-form. And a mixture containing the Z-form in any proportion. For example, the general formula (1-B) [in the formula, R ¹ , R ² , R ³ and R ⁴ have the same meanings as described above. ] Means that the coupling of the wavy lines includes an E-form, a Z-form or a mixture containing an E-form and a Z-form in an arbitrary ratio.

In addition, the compounds included in the present invention include optically active substances due to the presence of one or more asymmetric carbon atoms or asymmetric sulfur atoms, but the present invention includes all optically active substances or racemates. Including the body.
In addition, the compounds included in the present invention may have tautomers depending on the type of substituent, but the present invention is a mixture of all tautomers or tautomers contained in any proportion. It includes.

Among the compounds included in the present invention, those which can be made into an acid addition salt according to a conventional method are, for example, hydrohalogenated acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid and hydroiodide. Salts of inorganic acids such as salts, nitric acid, sulfuric acid, phosphoric acid, chloric acid, perchloric acid, salts of sulfonic acids 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, tartrate acid, oxalic acid, maleic acid, malic acid, succinic acid, benzoic acid, mandelic acid, ascorbic acid, lactic acid, gluconic acid, citric acid or It can be a salt of an amino acid such as glutamic acid or aspartic acid.
Alternatively, among the compounds included in the present invention, those which can be made into metal salts according to a conventional method are, 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 are shown below. Here, n- means normal, i- means iso, s- means secondary, and tert- means tertiary.

Examples of the "halogen atom" include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom. The notation of "halo" also represents these halogen atoms.

The notation "C _{a to} C _b alkyl" represents a linear or branched hydrocarbon group having _a to _b carbon atoms, for example, a methyl group, an ethyl group, an n-propyl group, or i-. Specific examples include 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. Selected within the specified number of carbon atoms.

The notation "halo (C _{a to} C _b ) alkyl" is a linear or branched chain consisting of _a to _b carbon atoms in which a hydrogen atom bonded to a carbon atom is arbitrarily substituted by a halogen atom. Representing a hydrocarbon group, where they are substituted by two or more halogen atoms, the halogen atoms may be the same 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, 1-fluoroethyl 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, 2-bromo-2,2-difluoroethyl group, 1,1,2,2-tetrafluoroethyl group, 2-chloro-1,1,2-trifluoroethyl group, 2-chloro-1 , 1,2,2-tetrafluoroethyl group, pentafluoroethyl group, 2,2-difluoropropyl group, 3,3,3-trifluoropropyl group, 3-bromo-3,3-difluoropropyl group, 2, 2,3,3-tetrafluoropropyl group, 2,2,3,3,3-pentafluoropropyl group, 1,1,2,3,3,3-hexafluoropropyl group, heptafluoropropyl group, 2, 2,2-Trifluoro-1- (methyl) ethyl group, 2,2,2-trifluoro-1- (trifluoromethyl) ethyl group, 1,2,2,2-tetrafluoro-1- (trifluoro) Specific examples include a methyl) ethyl group, a 2,2,3,4,5,4-hexafluorobutyl group, a 2,2,3,3,4,5,4-heptafluorobutyl group, and a nonafluorobutyl group. It is listed and selected within the range of each specified number of carbon atoms.

The notation "C _{a to} C _b cycloalkyl" represents a cyclic hydrocarbon group having _a to _b carbon atoms, and forms a monocyclic or complex ring structure from a 3-membered ring to a 6-membered ring. Can be done. Further, each ring may be optionally substituted with an alkyl group within a specified number of carbon atoms. For example, a cyclopropyl group, a 1-methylcyclopropyl group, a 2-methylcyclopropyl group, a 2,2-dimethylcyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group and the like are given as specific examples, and each designated carbon atom is given. Selected in a range of numbers.

The notation "C _{a to} C _b alkenyl" is a linear or branched chain having a number of carbon atoms of _a to _b , and unsaturated carbide having one or more double bonds in the molecule. Represents a hydrogen 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 groups and the like are given as specific examples, and are selected within the range of each specified number of carbon atoms.

The notation "halo (C _{a to} C _b ) alkenyl" is a linear or branched chain consisting of _a to _b carbon atoms in which hydrogen atoms bonded to carbon atoms are arbitrarily substituted by halogen atoms. Represents an unsaturated hydrocarbon group having one or more double bonds in the molecule. At this time, when substituted with two or more halogen atoms, the halogen atoms may be the same as each other or different from each other. For example, 2,2-dichlorovinyl group, 2-fluoro-2-propenyl group, 2-chloro-2-propenyl group, 3-chloro-2-propenyl group, 2-bromo-2-propenyl group, 3,3-difluoro -2-Propenyl group, 2,3-dichloro-2-propenyl group, 3,3-dichloro-2-propenyl group, 2,3,3-trifluoro-2-propenyl group, 2,3,3-trichloro- 2-propenyl group, 1- (trifluoromethyl) ethenyl group, 4,4-difluoro-3-butenyl group, 3,4,54-trifluoro-3-butenyl group, 3-chloro-4,4,5- A trifluoro-2-butenyl group or the like is given as a specific example, and each is selected within the specified number of carbon atoms.

The notation "C _{a to} C _b alkynyl" is an unsaturated hydrocarbon having a linear or branched chain consisting of _a to _b carbon atoms and having one or two or more triple bonds in the molecule. Specific examples thereof include an ethynyl group, a propargyl group, a 2-butynyl group, a 3-butynyl group, a 1-pentynyl group, a 1-hexynyl group, etc. To.

The notation "halo (C _{a to} C _b ) alkynyl" is a linear or branched chain consisting of _a to _b carbon atoms in which hydrogen atoms bonded to carbon atoms are arbitrarily substituted by halogen atoms. Represents an unsaturated hydrocarbon group having one or more triple bonds in the molecule. At this time, when substituted with two or more halogen atoms, the halogen atoms may be the same as each other or different from each other. For example, 2-chloroethynyl group, 2-bromoethynyl group, 2-iodoethynyl group, 3-chloro-2-propynyl group, 3-bromo-2-propynyl group, 3-iodo-2-propynyl group, 4,4. Specific examples thereof include 4-trifluoro-2-butynyl group, and each group is selected within the specified number of carbon atoms.

The notation "C _{a to} C _b alkoxy" represents an alkyl-O-group having the above-mentioned meaning consisting of _a to _b carbon atoms. Specific examples thereof include methoxy group, ethoxy group, n-propyloxy group, i-propyloxy group, n-butyloxy group, i-butyloxy group, s-butyloxy group, tert-butyloxy group and 2-ethylhexyloxy group. It is listed and selected in the range of each specified number of carbon atoms.

The notation "halo (C _{a to} C _b ) alkoxy" represents the haloalkyl-O-group having the above-mentioned meaning consisting of _a to _b carbon atoms. For example, difluoromethoxy group, trifluoromethoxy group, chlorodifluoromethoxy group, bromodifluoromethoxy group, 2-fluoroethoxy group, 2-chloroethoxy group, 2,2,2-trifluoroethoxy group, 1,1,2,2 , -Tetrafluoroethoxy group, 2-chloro-1,1,2-trifluoroethoxy group, 1,1,2,3,3,3-hexafluoropropyloxy group and the like are given as specific examples, and each designation is given. It is selected in the range of the number of carbon atoms in.

The notation "C _{a to} C _b alkylthio" represents an alkyl-S-group having the above-mentioned meaning consisting of _a to _b carbon atoms. Specific examples thereof include methylthio group, ethylthio group, n-propylthio group, i-propylthio group, n-butylthio group, i-butylthio group, s-butylthio group, tert-butylthio group and the like, and each designated carbon atom Selected in a range of numbers.

The notation of "halo (C _{a to} C _b ) alkylthio" represents the haloalkyl-S-group having the above-mentioned meaning consisting of _a to _b carbon atoms. For example, difluoromethylthio group, trifluoromethylthio group, chlorodifluoromethylthio group, bromodifluoromethylthio group, 2,2,2-trifluoroethylthio group, 1,1,2,2-tetrafluoroethylthio group, 2-chloro- 1,1,2-trifluoroethylthio group, pentafluoroethylthio group, 1,1,2,3,3,3-hexafluoropropylthio group, heptafluoropropylthio group, 1,2,2,2- Specific examples thereof include a tetrafluoro-1- (trifluoromethyl) ethylthio group and a nonafluorobutylthio group, which are selected within the specified number of carbon atoms.

The notation "C _{a to} C _b alkylsulfinyl" represents an alkyl-S (O) -group having the above-mentioned meaning consisting of _a to _b carbon atoms. Specific examples include methylsulfinyl group, ethylsulfinyl group, n-propylsulfinyl group, i-propylsulfinyl group, n-butylsulfinyl group, i-butylsulfinyl group, s-butylsulfinyl group, tert-butylsulfinyl group and the like. It is selected in the range of each specified number of carbon atoms.

The notation "halo (C _{a to} C _b ) alkylsulfinyl" represents the haloalkyl-S (O) -group having the above-mentioned meaning consisting of _a to _b carbon atoms. For example, difluoromethylsulfinyl group, trifluoromethylsulfinyl group, chlorodifluoromethylsulfinyl group, bromodifluoromethylsulfinyl group, 2,2,2-trifluoroethylsulfinyl group, 1,2,2,2-tetrafluoro-1- ( Specific examples include a trifluoromethyl) ethylsulfinyl group and a nonafluorobutylsulfinyl group, which are selected within the specified number of carbon atoms.

The notation "C _{a to} C _b alkylsulfonyl" represents an alkyl-SO ₂ -group having the above-mentioned meaning consisting of _a to _b carbon atoms. Specific examples thereof include methylsulfonyl group, ethylsulfonyl group, n-propylsulfonyl group, i-propylsulfonyl group, n-butylsulfonyl group, i-butylsulfonyl group, s-butylsulfonyl group, tert-butylsulfonyl group and the like. Is selected within the range of each specified number of carbon atoms.

The notation "halo (C _{a to} C _b ) alkylsulfonyl" represents the haloalkyl-SO ₂ -group having the above meaning consisting of _a to _b carbon atoms. For example, difluoromethylsulfonyl group, trifluoromethylsulfonyl group, chlorodifluoromethylsulfonyl group, bromodifluoromethylsulfonyl group, 2,2,2-trifluoroethylsulfonyl group, 1,1,2,2-tetrafluoroethylsulfonyl group, Specific examples include 2-chloro-1,1,2-trifluoroethylsulfonyl groups, etc., which are selected within the specified number of carbon atoms.

The notation "C _{a to} C _b alkylcarbonyl" 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, heptanoyle group and the like are given as specific examples, and the number of carbon atoms specified for each is specified. It is selected in the range of.

The notation "C _{a to} C _b alkoxycarbonyl" represents an alkyl-OC (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, s-butoxycarbonyl group, tert-butoxycarbonyl group, 2-ethyl A hexyloxycarbonyl group or the like is given as a specific example, and each is selected within the specified number of carbon atoms.

"C _{a to} C _b cycloalkyl (C _{d to} C _e ) alkyl", "C _{a to} C _b alkoxy (C _{d to} C _e ) alkyl", "halo (C _{a to} C _b ) alkoxy (C _{d to} C)" _e ) Alkoxy ”,“ C _{a to} C _b alkylthio (C _{d to} C _e ) alkyl ”,“ halo (C _{a to} C _b ) alkyl thio (C _{d to} C _e ) alkyl”, “C _{a to} C _b alkyl sulfinyl” (C _{d to} C _e ) alkyl "," halo (C _{a to} C _b ) alkyl sulfinyl (C _{d to} C _e ) alkyl "," C _{a to} C _b alkylsulfonyl (C _{d to} C _e ) alkyl "," Notations such as "halo (C _{a to} C _b ) alkylsulfonyl (C _{d to} C _e ) alkyl" or "cyano (C _{d to} C _e ) alkyl" have the above meanings, respectively, C _{a to} C _b cycloalkyl, respectively. C _{a to} C _b alkoxy, halo (C _{a to} C _b ) alkoxy, C _{a to} C _b alkylthio, halo (C _{a to} C _b ) alkyl thio, C _{a to} C _b alkyl sulfinyl, halo (C _{a to} C _b ) Alkoxy sulfinyl, C _{a to} C _b alkylsulfonyl, halo (C _{a to} C _b ) alkylsulfonyl or cyano, the above-mentioned number of carbon atoms in which the hydrogen atom bonded to the carbon atom is arbitrarily substituted is composed of d to e. It represents an alkyl group, which means, and is selected in the range of each specified number of carbon atoms.

Notations such as "C _{a to} C _b alkoxy (C _{d to} C _e ) alkoxy" are carbon atoms in which hydrogen atoms bonded to carbon atoms are arbitrarily substituted by C _{a to} C _b alkoxy, which have the above meanings, respectively. It represents an alkoxy group having the above meaning of a number consisting of d to e, and is selected in the range of each specified number of carbon atoms.

"Substituted in ^{R 1a} _(C ^{a ~C} _b) alkyl", "substituted in ^{R 3a} _(C ^{a ~C} _b) alkyl", "substituted in ^{R 10a} _(C ^{a ~C} _b) alkyl" , "substituted in ^{R 11a} _(C ^{a ~C} _b) alkyl", "substituted in ^{R 12a} _(C ^{a ~C} _b) alkyl", "substituted in ^{R 18a} _(C ^{a ~C} _b) alkyl The notation such as "consists of a to ^b carbon atoms in which hydrogen atoms bonded to carbon atoms are arbitrarily substituted by arbitrary R ^1a , R ^3a , R ^10a , R ^11a , R ^12a or R ^18a . It represents an alkyl group having the above meaning and is selected in the range of each specified number of carbon atoms. At this time, when two or more substituents R ^1a , R ^3a , R ^10a , R ^11a , R ^12a or R ^18a on the respective (C _{a to} C _b ) alkyl groups are present, the respective R ^1a and R ^{3a are present.} , R ^10a , R ^11a , R ^12a or R ^18a may be the same or different from each other.

The notation such as "(C _{a to} C _b ) cycloalkyl substituted with R ^1b " indicates that the number of carbon atoms in which the hydrogen atom bonded to the carbon atom is arbitrarily substituted by any R 1 ^b is from a to ^b . Represents a cycloalkyl group having the above-mentioned meaning, and is selected in the range of each specified number of carbon atoms. At this time, when two or more substituents R ^1b on each (C _{a to} C _b ) cycloalkyl group are present, each R ^1b may be the same or different from each other.

"By ^{R 13} is to form a _C 2 -C ₆ alkylene chain together with ^{R 14,} represents the formation of a 3- to 7-membered ring together with the nitrogen atom ^{to which R 13} and ^{R 14} are attached, this this time alkylene chain is optionally replaced by O, S, specific examples of the notation S (O), S (O ) 2 or N ^{(R 15)} may comprise one of ", for example aziridine, azetidine, pyrrolidine, oxazolidine, thiazolidine, imidazolidine Examples thereof include lysine, piperidine, morpholine, thiomorpholine, piperazine, homopiperidine and the like, and each is selected within a specified number of atoms.

Next, a method for producing the compound of the present invention represented by the formula (1) will be described below. The compound of the present invention can be produced, for example, by the following production methods 1 to 6.

（式中、Ｒ^１、Ｒ^２、Ｒ^３及びＲ^４は前記と同じ意味を表し、Ｌ^１はハロゲン原子、−ＯＳＯ_２ＣＨ_３、−ＯＳＯ_２ＣＦ_３等の脱離基を表す。） Manufacturing method 1
Among the compounds of the present invention represented by the formula (1), the compounds represented by (1-A), (1-B) and (1-C) are, for example, the compound (2-1) and the compound. It can be produced by reacting with (50).

(In the formula, R ¹ , R ² , R ³ and R ⁴ have the same meanings as described above, and L ¹ represents a halogen atom, -OSO ₂ CH ₃ , -OSO ₂ CF _{3 and} other leaving groups.)

Compounds (1-A), (1-B) and (1-C) cause compound (2-1) and compound (50) to react in a solvent or in the absence of a solvent, in some cases in the presence of a base. Can be manufactured by.
When a solvent is used, the solvent may be inert to the reaction, for example, N, N-dimethylformamide, N, N-dimethylacetamide, acetonitrile, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolinone, water. Polar solvents such as methanol, ethanol, propanol, 2-propanol, alcohols such as ethylene glycol, ethers such as diethyl ether, tetrahydrofuran and diphenyl ether, aromatic hydrocarbons such as benzene, toluene and xylene, methylene chloride and chloroform. , Halogenized hydrocarbons such as carbon tetrachloride, and aliphatic hydrocarbons such as pentane and n-hexane. These solvents may be used alone or in combination of two or more of them.
The reaction can be carried out in the presence of a base. Examples of the base include pyridine, 2,6-rutidine, triethylamine, diisopropylethylamine, tributylamine, 4- (dimethylamino) pyridine, 1,4-diazabicyclo [2.2.2] octane (DABCO), 1,8-. Organic bases such as diazabicyclo [5.4.0] -7-undecene (DBU) or 1,5-diazabicyclo [4.3.0] -5-nonen (DBN), sodium hydroxide, potassium hydroxide, hydrogen Examples thereof include inorganic bases such as sodium carbonate, sodium hydrogen carbonate, potassium carbonate and cesium carbonate. The amount of base used is 0 for 1 equivalent of compound (2-1).
.. It can be used in 1 to 100 equivalents, preferably 1 to 20 equivalents.
The reaction temperature can be set at any temperature from −80 ° C. to the reflux temperature of the reaction mixture, preferably in the range of 0 ° C. to the reflux temperature of the reaction mixture.
The reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but is usually 5 minutes to 100 hours and can be arbitrarily set, preferably 1 to 48 hours.
As for the amount of the substrate used, compound (50) can be used in an amount of 0.5 to 50 equivalents with respect to 1 equivalent of compound (2-1), preferably 1 to 20 equivalents.
Some of the compounds (2-1) 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 methods described in International Publication No. 2014/192936 and the like.
Some of the compound (50) are known compounds, and some are commercially available.

（式中、Ｒ^１、Ｒ^２、Ｒ^３及びＲ^４は前記と同じ意味を表す。） Manufacturing method 2
Compound (1-A) can be produced, for example, by reacting compound (3-1) with compound (4-1).

(In the formula, R ¹ , R ² , R ³ and R ⁴ have the same meanings as described above.)

Compound (1-A) is a mixture of compound (3-1) and compound (4-1) in a solvent or in the absence of a solvent in the presence of a dehydration condensing agent, in some cases in the presence of a base, and in some cases in the presence of additives. It can be manufactured by reacting below.
When a solvent is used, the solvent may be inert to the reaction, for example, N, N-dimethylformamide, N, N-dimethylacetamide, acetonitrile, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolinone, water. Polar solvents such as methanol, ethanol, propanol, 2-propanol, alcohols such as ethylene glycol, ethers such as diethyl ether, tetrahydrofuran and diphenyl ether, aromatic hydrocarbons such as benzene, toluene and xylene, methylene chloride and chloroform. , Halogenized hydrocarbons such as carbon tetrachloride, and aliphatic hydrocarbons such as pentane and n-hexane. These solvents may be used alone or in combination of two or more of them.
Examples of the dehydration condensing agent include 1H-benzotriazole-1-yloxytris (dimethylamino) phosphonium hexafluorophosphate, N, N'-dicyclohexylcarbodiimide, and 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride. Examples thereof include salts and 2-chloro-1-methylpyridinium iodide. The amount of the dehydration condensing agent used can be 0.1 to 100 equivalents with respect to 1 equivalent of compound (3-1), preferably 1 to 20 equivalents.
The reaction can be carried out in the presence of a base. Examples of the base include organic bases such as pyridine, triethylamine and 4- (dimethylamino) pyridine, and inorganic bases such as sodium hydroxide, potassium carbonate and cesium carbonate. The amount of the base used can be 0.1 to 100 equivalents with respect to 1 equivalent of compound (3-1), preferably 1 to 20 equivalents.
The reaction can be carried out in the presence of additives. Examples of the additive include 3H- [1,2,3] triazolo [4,5-b] pyridine-3-ol, 1-hydroxybenzotriazole and the like. The amount of the additive used can be 0.1 to 100 equivalents with respect to 1 equivalent of compound (3-1), preferably 1 to 20 equivalents.
The reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but is usually 5 minutes to 100 hours and can be arbitrarily set, preferably 1 to 48 hours.
As for the amount of the substrate used, the compound (4-1) can be used in an amount of 0.5 to 50 equivalents with respect to 1 equivalent of the compound (3-1), preferably 1 to 20 equivalents.
Some of the compounds (4-1) 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 methods described in International Publication No. 2008/006540, International Publication No. 2014/192936, and the like.

（式中、Ｒ^１、Ｒ^２、Ｒ^３及びＲ^４は前記と同じ意味を表し、Ｘ^１はハロゲン原子を表す。） Manufacturing method 3
Compound (1-A) can be produced, for example, by reacting compound (3-1) with compound (4-2).

(In the formula, R ¹ , R ² , R ³ and R ⁴ have the same meanings as described above, and X ¹ represents a halogen atom.)

Compound (1-A) can be produced by reacting compound (3-1) with compound (4-2) in a solvent or in the absence of a solvent, in some cases in the presence of a base.
When a solvent is used, the solvent may be inert to the reaction, for example, N, N-dimethylformamide, N, N-dimethylacetamide, acetonitrile, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolinone, water. Polar solvents such as methanol, ethanol, propanol, 2-propanol, alcohols such as ethylene glycol, ethers such as diethyl ether, tetrahydrofuran and diphenyl ether, aromatic hydrocarbons such as benzene, toluene and xylene, methylene chloride and chloroform. , Halogenized hydrocarbons such as carbon tetrachloride, and aliphatic hydrocarbons such as pentane and n-hexane. These solvents may be used alone or in combination of two or more of them.
The reaction can be carried out in the presence of a base. Examples of the base include organic bases such as pyridine, triethylamine and 4- (dimethylamino) pyridine, and inorganic bases such as sodium hydroxide, potassium carbonate and cesium carbonate. The amount of the base used can be 0.1 to 100 equivalents with respect to 1 equivalent of compound (3-1), preferably 1 to 20 equivalents.
The reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but is usually 5 minutes to 100 hours and can be arbitrarily set, preferably 1 to 48 hours.
As for the amount of the substrate used, the compound (4-2) can be used in an amount of 0.5 to 50 equivalents with respect to 1 equivalent of the compound (3-1), preferably 1 to 20 equivalents.
Some of the compounds (4-2) are known compounds and can be synthesized by a method according to a known method described in the literature. Known methods known in the literature include, for example, International Publication No. 2014/192.
The method described in No. 936 and the like can be mentioned.

（式中、Ｒ^１、Ｒ^２、Ｒ^３及びＲ^４は前記と同じ意味を表し、Ｘ^２はハロゲン原子を表す。） Manufacturing method 4
Compound (1-B) can be produced, for example, by reacting compound (5-1) with compound (4-1).

(In the formula, R ¹ , R ² , R ³ and R ⁴ have the same meanings as described above, and X ² represents a halogen atom.)

Compound (1-B) can be produced by reacting compound (5-1) with compound (4-1) according to the method described in Production Method 2.

（式中、Ｒ^１、Ｒ^２、Ｒ^３、Ｒ^４、Ｘ^１及びＸ^２は前記と同じ意味を表す。） Manufacturing method 5
Compound (1-B) can be produced, for example, by reacting compound (5-1) with compound (4-2).

(In the formula, R ¹ , R ² , R ³ , R ⁴ , X ¹ and X ² have the same meanings as described above.)

Compound (1-B) can be produced by reacting compound (5-1) with compound (4-2) according to the method described in Production Method 3.

（式中、Ｒ^１、Ｒ^２、Ｒ^３及びＲ^４は前記と同じ意味を表し、Ｗ^１は水素原子、ナトリウム原子又はカリウム原子を表す。） Manufacturing method 6
Compound (1-C) can be produced, for example, by reacting compound (6-1) with compound (51).

(In the formula, R ¹ , R ² , R ³ and R ⁴ have the same meanings as described above, and W ¹ represents a hydrogen atom, a sodium atom or a potassium atom.)

Compound (1-C) can be produced by reacting compound (6-1) with compound (51) in a solvent or in the absence of a solvent, in some cases in the presence of a base.
When a solvent is used, the solvent may be inert to the reaction, for example, N, N-dimethylformamide, N, N-dimethylacetamide, acetonitrile, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolinone, water. Polar solvents such as methanol, ethanol, propanol, 2-propanol, alcohols such as ethylene glycol, ethers such as diethyl ether, tetrahydrofuran and diphenyl ether, aromatic hydrocarbons such as benzene, toluene and xylene, methylene chloride and chloroform. , Halogenized hydrocarbons such as carbon tetrachloride, and aliphatic hydrocarbons such as pentane and n-hexane. These solvents may be used alone or in combination of two or more of them.
The reaction can be carried out in the presence of a base. Examples of the base include pyridine, 2,6-rutidine, triethylamine, diisopropylethylamine, tributylamine, 4- (dimethylamino) pyridine, 1,4-diazabicyclo [2.2.2] octane (DABCO), 1,8-. Organic bases such as diazabicyclo [5.4.0] -7-undecene (DBU) or 1,5-diazabicyclo [4.3.0] -5-nonen (DBN), sodium hydroxide, potassium hydroxide, hydrogen Examples thereof include inorganic bases such as sodium carbonate, sodium hydrogen carbonate, potassium carbonate and cesium carbonate. The amount of the base used can be 0.1 to 100 equivalents with respect to 1 equivalent of compound (6-1), preferably 1 to 20 equivalents.
The reaction temperature can be set at any temperature from −80 ° C. to the reflux temperature of the reaction mixture, preferably in the range of 0 ° C. to the reflux temperature of the reaction mixture.
The reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but is usually 5 minutes to 100 hours and can be arbitrarily set, preferably 1 to 48 hours.
As for the amount of the substrate used, compound (51) can be used in an amount of 0.5 to 50 equivalents with respect to 1 equivalent of compound (6-1), preferably 1 to 20 equivalents.
Some of the compound (51) are known compounds, and some are commercially available.

（式中、Ｒ^３、Ｒ^４及びＬ^１は前記と同じ意味を表す。） The compound (3-1) used in the production method 2 and the production method 3 can be produced, for example, according to the production route represented by the following reaction formula.
Reaction equation 1

(In the formula, R ³ , R ⁴ and L ¹ have the same meanings as described above.)

Step 1: The compound (52-a) is reacted with dicarbonate-tert-butyl according to a known method known in the literature, for example, the method described in JP-A-2011-513293. 52-b) can be manufactured. Some of the compounds (52-a) are known compounds, and some are commercially available.
Step 2: Compound (52-c) can be produced by reacting compound (52-b) with compound (50) according to the method described in Production Method 1.
Step 3: By reacting compound (52-c) with an acid such as hydrochloric acid or trifluoroacetic acid according to a known method known in the literature, for example, the method described in JP-A-2011-513293. Compound (3-1) can be produced.

（式中、Ｒ^３及びＲ^４は前記と同じ意味を表し、Ｘ^２はハロゲン原子を表す。） The compound (5-1) used in the production method 4 and the production method 5 can be produced, for example, according to the production route represented by the following reaction formula.
Reaction equation 2

(In the formula, R ³ and R ⁴ have the same meanings as described above, and X ² represents a halogen atom.)

Compound (5-1) can be produced by reacting compound (52-a) with compound (54) in a solvent or without a solvent.
When a solvent is used, the solvent may be inert to the reaction, for example, N, N-dimethylformamide, N, N-dimethylacetamide, acetonitrile, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolinone, water. Polar solvents such as methanol, ethanol, propanol, 2-propanol, alcohols such as ethylene glycol, ethers such as diethyl ether, tetrahydrofuran and diphenyl ether, aromatic hydrocarbons such as benzene, toluene and xylene, methylene chloride and chloroform. , Halogenized hydrocarbons such as carbon tetrachloride, and aliphatic hydrocarbons such as pentane and n-hexane. These solvents may be used alone or in combination of two or more of them.
The reaction temperature can be set at any temperature from −80 ° C. to the reflux temperature of the reaction mixture, preferably in the range of 0 ° C. to the reflux temperature of the reaction mixture.
The reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but is usually 5 minutes to 100 hours and can be arbitrarily set, preferably 1 to 48 hours.
As for the amount of the substrate used, compound (54) can be used in an amount of 0.5 to 50 equivalents with respect to 1 equivalent of compound (52-a), preferably 1 to 20 equivalents.
Some of the compounds (52-a) are known compounds, and some are commercially available.

（式中、Ｒ^１、Ｒ^２及びＲ^４は前記と同じ意味を表す。） The compound (6-1) used in the production method 6 can be produced, for example, according to the production route represented by the following reaction formula.
Reaction equation 3

(In the formula, R ¹ , R ² and R ⁴ have the same meanings as described above.)

Compound (2-1) is reacted with a chlorinating agent such as thionyl chloride, phosphorus oxychloride or phosphorus pentachloride according to a known method known in the literature, for example, the method described in International Publication No. 2015/087834. The compound (6-1) can be produced by allowing the compound (6-1) to be produced.

In the reactions of Production Methods 1 to 6 and Reaction Formulas 1 to 3, the reaction mixture after completion of the reaction is directly concentrated or dissolved in an organic solvent, washed with water and then concentrated or put into ice water, and the usual post-treatment such as concentration after extraction of the organic solvent is performed. The desired compound of the present invention can be obtained. When the need for purification arises, it can be separated and purified by any purification method such as recrystallization, column chromatograph, thin layer chromatograph, and liquid chromatograph sorting.

The compound of the present invention can be used as a herbicide for paddy fields in any of the treatment methods of soil treatment and foliage treatment under flooding. Paddy weeds include, for example, Azegaya (chinese sprangletop, Leptochloa chinensis), Onia Zegaya (bearded sprangletop, Leptochloa fascicularis), Inubie (barnyard grass, Echinochloa crus-galli), Kohimebier (junglerice, Echinochloa colonum) oryzicola), Taiwanese grass (southern cutgrass, Leersia hexandra), Knotgrass, Paspalum distichum, Taiwanese grass (saramollagrass, Ischaemum rugosum), grass grass (itchgrass, Rottboellia cochinchinensis) , Alexandergrass, Brachiaria plantaginea, large crabgrass, Digitaria sanguinalis, crowfoot grass, Dactyloctenium aegyptium, barnyardgrass (goosegrass, Eleusine indica), weed grass (red rice) , Cynodon dactylon, as well as grasses (Gramineae) weeds represented by fall panicum, Panicum dichotomiflorum, Eleocharis kuroguwai, globe fringerush, Fimbristylis miliacea, Inuhotarui (japanese bulrush, Schoenlect) Shizui (Schoenoplectus nipponicus), Barnyardgrass (ricefield bulrush, Schoenoplectus) mucronatus, nutsedge (Cyperus serotinus), nutsedge (small flower umbrella sedge, Cyperus difformis), nutsedge (rice flat sedge, Cyperus iria), nutsedge (purple nutsedge, Cyperus rotundus), nutsedge (yellow nutsedge, Cyperus) Cosmopolitan bulrush, Bolboschoenus martimus), etc., Nutsedge family (Cyperaceae) weeds, Heraomodaka (water plantain, Alisma canaliculatum), Urikawa (pygmy arrowhead, Sagittaria pygmaea), and Omodaka (threeleaf arrowhead, git) Alismataceae (Alismataceae) weeds, nutsedges (asian spiderwort, Murdannia keisak), and nutsedges (Commelinaceae) weeds represented by benghal dayflower, Commelina benghalensis, nutsedge (heartleaf false pickerelweed, Monochoria) oval-leafed pondweed, Monochoria vaginalis), American nutsedge (ducksalad, Heteranthera limosa), and Nuttederiaceae weeds represented by water hyacinth, Eichhornia crassipes, threestamen waterwort, latin
Lythraceae (Elatinaceae) weeds represented by triandra, Lythraceae (Lythraceae) weeds represented by redstem, Ammannia coccinea (redstem, Ammannia coccinea), and Mexican primrose (Ludwigia epilobioides) , And the Evening Primrose (Oenotheraceae) weeds, such as Mexican primrose-willow (Ludwigia octovalvis), rushlike dopatrium, Dopatrium junceum, Gratiola japonica, dwarf ambulia, Limnophila ses. prostrate false pimpernel, Lindernia pyxidaria), and Lythraceae (Scrophulariaceae) weeds represented by American Azena (yellowseed false pimpernel, Lindernia dubia), alligator weed, Alternan
Thera philoxeroides), Amaranthaceae weeds represented by spiny amaranth, Amaranthus spinosus, etc., Polygonaceae weeds represented by water pepper, Polygonum hydropiper, etc., gooseweed, Sphenoclea Amaranthaceae (Sphenocleaceae) weeds represented by zeylanica, etc., Aeschynomene indica, Aeschynomene indica, hemp sesbania,
Legumes (Fabaceae) weeds such as Sesbania exaltata, American Sendangusa (devil's beggarticks, Bidens frondosa), Bidens tripartita (three-lobe beggarticks, Bidens)
tripartita), Takasaburo (false daisy, Eclipta prostrata), Asteraceae weeds represented by goatweed, Ageratum conyzoides, etc., Convolvulaceae represented by swamp morningglory, Ipomoea aquatica, etc. ) Weeds, Asteraceae (Marsileaceae) represented by water clover, Marsilea minuta, etc., Asteraceae (common duckmeat, Spirodela polyrhiza), and Asteraceae (duckweed, Lemna paucicostata), etc. Examples include weeds and weeds of the family Asteraceae (Potamogetonaceae) represented by roundleaf pondweed (Potamogeton distinctus) and the like.

In addition, the compound of the present invention can be used as a herbicide for upland fields and orchards in any of the treatment methods of soil treatment, soil mixing treatment and foliage treatment. Upland weeds include, for example, fall panicum, Panicum dichotomiflorum, shuttercane, Sorgham bicolor, johnson grass, Sorghum halepense, barnyard grass, Echinochloa crus-galli var. Crus-galli. , Himeinubie (cockspur grass, Echinochloa crus-galli var. Praticola), Cultivated Bier (japanese barnyard millet, Echinochloa utilis), Mehishiba (southern crabgrass, Digitaria ciliaris), Susukimehishiba (sourgrass, Digitaria insularis) horizontalis), crow wheat (wild oat, Avena fatua), blackgrass (blackgrass, Alopecurus myosuroides), shortawn foxtail, Alopecurus aequalis, windgrass, Apera spica-venti, downy brome, Bromus tector Rats (italian ryegrass, Lolium multiflorum), Boumugi (rigid ryegrass, Lolium rigidum), Himekana Leak Sayoshi (littleseed canarygrass, Phalaris minor), Suzumenokatabira (annual bluegrass, Poa annua), Ohishiba (goosegrass) , Setaria viridis), Aquinoenocologsa (giant foxtail, Setaria faberi), Signalgrass, Brachiaria decumbens, and Southern sa Poaceae weeds represented by ndbur, Cenchrus echinatus), Cyperaceae weeds represented by purple nutsedge, Cyperus rotundus, etc., black nightshade, Solanum nigrum, and Shirobanayoush Amaranthaceae (Solanaceae) weeds represented by jimsonweed (Datura stramonium), grasses (velvetleaf, Abutilon theophrasti), and grasses (Malvaceae) represented by American goldfish (prickly sida, Sida spinosa). , Malva asagao (tall morning-glory, Ipomoea purpurea), American asagao (ivyleaf morning-glory, Ipomoea hederacea), and Amaranthaceae (Convolvulaceae) weeds and grasses (purple amaranth) represented by Japanese bindweed, Calystegia hederacea. , Amaranthus lividus), Amaranthus retroflexus (redroot pigweed, Amaranthus retroflexus), Amaranthus palmeri (palmer amaranth, Amaranthus palmeri), and Amaranthaceae (Amaranthaceae) weeds represented by tall waterhemp, Amaranthus tuberculatus. common cocklebur, Xanthium strumarium), common ragweed,
Ambrosia artemisiifolia), Giant ragweed (Ambrosia trifida), Horseweed (horseweed, Conyza canadensis), Sunflower (common sunflower, Helianthus annuus), Koshikagiku (pineappleweed, Matricaria matricarioides), Shaggy soldier (Pineappleweed, Matricaria matricarioides), Shaggy soldier (Canada thistle
, Cirsium arvense), groundsel (common groundsel, Senecio vulgaris), and Asteraceae weeds represented by annual fleabane, Erigeron annuus, rorippa indica (variableleaf yellowcress, Rorippa indica), wild garashi (wild)
Mustard, Sinapis arvensis), Chenopodiaceae (Brassicaceae) weeds represented by shepherd's purse, Capsella bursa-pastoris, oriental lady's thumb, Persicaria longiseta, and wild buckwheat, Polygonum convolvulus, etc. Represented Polygonaceae weeds, Portulacaceae weeds represented by common purslane, Portulaca oleracea, etc., Labiatae (lambsquarters, Chenopodium album), core kaza (figleaved goosefoot, Chenopodium ficifolium), Hokigi (kochi) , Kochia scoparia, Chenopodiaceae weeds represented by Russian thistle, Salsola tragus, etc., Caryophyllaceae weeds represented by common chickweed, Stellaria media, etc., Persian Weeds of the family Chenopodiaceae (Plantaginaceae) represented by speedwell, Veronica persica, etc., weeds of the family Chenopodiaceae (Commelinaceae) represented by the spurges (asiatic dayflower, Commelina communis), and the weeds of the family Chenopodiaceae (Commelinaceae) henbit, Lamium amplexicaule), Labiatae (Lamiaceae) weeds represented by purple deadnettle, Lamium purpureum, etc., Spodoptera (wild poinsettia, Euphorbia heterophylla), and Onishikisou (spotted spurge, Euphorbia maculata), etc. Representative Chenopodiaceae (Euphorbiaceae) weeds , Galium spurium (false cleavers, Galium spurium), and Rubiaceae weeds represented by Asian madder, Rubia akane, Violaceae weeds represented by pansy, Viola tricolor, etc. Papaveraceae weeds represented by filed poppy, Papaver rhoeas, and Fabaceae weeds represented by hemp sesbania, Sesbania exaltata, and sicklepod, Cassia obtusifolia. , And weeds of the family Rubiaceae (Oxalidaceae) represented by creeping woodsorrel, Oxalis corniculata and the like.

Further, the compound of the present invention can be used, for example, for industrial facilities such as embankment slopes, riverbeds, road shoulders and slopes, railway beds, park green spaces, grounds, parking lots, airports, factories and storage facilities, fallow land, or , Non-agricultural land that needs to control the growth of weeds such as closed land in the city, or a wide range of weeds that occur in orchards, pastures, lawns, forests, etc. can be weeded. The weeds include, in addition to those mentioned in the field and orchard weeds, conyza (annual bluegrass, Poa annua), dandelion, Taraxacum officinale, erigeron bonariensis (hairy fleabane, Conyza bonariensis), conyza bonariensis (horse). canadensis, erigeron sumatren (guernsey fleabane, Conyza sumatrensis), wavy bittercress, cardamine flexuosa, white clover, trifolium repens, lawn pennywort, hydrocotyle sibthorpioides Green kyllinga, Kyllinga brevifolia), Sugina (field horsetail, Equisetum arvense) and the like.

When 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 penetrant, a spreading agent, a thickener, an antifreeze agent, a binder, and a solid. Add a binder, a disintegrant, a decomposition inhibitor, etc., and use it in any formulation such as wettable powder, emulsion, flowable agent, dry flowable agent, liquid agent, powder agent, granule or gel agent. be able to. Further, from the viewpoint of labor saving and safety improvement, the preparation of any of the above dosage forms can be encapsulated in a water-soluble package and provided.

Examples of the solid carrier include natural mineral substances such as quartz, kaolinite, pyrophyllite, sericite, talc, bentonite, acidic clay, attapulsite, zeolite and diatomaceous earth, and inorganic substances such as calcium carbonate, ammonium sulfate, sodium sulfate and potassium chloride. Examples include salts, synthetic silicic acid and synthetic silicate.
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. Examples include 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 alkylaryl ether, polyoxyethylene styrylphenyl ether, polyoxyethylene polyoxypropylene block copolymer, polyoxyethylene fatty acid ester, sorbitan fatty acid ester and polyoxyethylene sorbitan. Nonionic surfactants such as fatty acid esters, alkyl sulfates, alkylbenzene sulfonates, lignin sulfonates, alkyl sulfosuccinates, naphthalene sulfonates, alkylnaphthalene sulfonates, salts of formalin condensates of naphthalene sulfonic acid, Anionic surfactants such as salts of formalin condensates of alkylnaphthalene sulfonic acid, polyoxyethylene alkylaryl ether sulfates and phosphates, polyoxyethylene styrylphenyl ether sulfates and phosphates, polycarboxylates and polystyrene sulfonates, Examples thereof include cationic surfactants such as alkylamine salts and alkyl quaternary ammonium salts, and amphoteric surfactants such as amino acid type and betaine type.
The content of these surfactants is not particularly limited, but is usually preferably in the range of 0.05 to 20 parts by weight with respect to 100 parts by weight of the preparation of the present invention. In addition, 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 kinds of herbicides, various insecticides, fungicides, plant growth regulators, synergists and the like at the time of preparation or spraying, if necessary.
In particular, by applying the mixture with other herbicides, it is expected that the cost can be reduced by reducing the amount of the applied drug, the herbicide spectrum can be expanded by the synergistic action of the mixed agents, and a higher herbicide effect can be expected. At this time, it is possible to combine with a plurality of known herbicides at the same time.

Preferred herbicides to be used in combination with the compounds of the present invention include, for example, 4-CPA, 4-CPA salts (4-CPA-salts), 4-CPB, 4-CPP, 2,4-D (2). , 4-PA), 2,4-D salts (2,4-D-salts), 2,4-D esters (2,4-D-esters), 3,4-DA, 2,4- DB, 2,4-DB salts (2,4-DB-salts), 2,4-DB esters (2,4-DB-esters), 3,4-DB, 2,4-DEB, 2, 4-DEP, 3,4-DP, 2,4,5-T, 2,4,5-T salts (2,4,5-T-salts), 2,4,5-T esters (2) , 4,5-T-esters), 2,4,5-TB (2,4,5-TB), 2,3,6-TBA (2,3,6-TBA, TCBA), 2,3 6-TBA salts (2,3,6-TBA-salts), acetatechol, asifluorphen, asifluorphen-methyl, asifluorfen-sodium, Acronifen, achlorein, alacchol, alydochlor, CDAA, alloxydim, alloxydim-sodium, allyl alcohol, allyl alcohol, allyl alcohol. (Ametridione), amethrin, amibuzin, amicarbazone, amidochlor, amidosulfuron, aminocyclopyrachromol, aminocyclopyrachlor, aminocyclopyrroxychlor. , Aminocyclopyracrol-potassium, aminopyrlide, aminopyrlide-salts, amiprophos, amiprophos, amiprophos, amiprophos Minotriazole, ATA), ammonium sulfamate (AMS), anilophos, anisuron, ashlum, ashram salt (asulam-salts), atrazine atrazine atrazine atrazine (Azafenidin), azimusulfuron, aziprothrin (aziprotrine, azyprotrin), barban (CBN), 1BCPC, beflubutamid, beflubutammid, beflubutamim, beflubutamide M (beflubutamid), beflubutamid, beflubutamid. ), Benazoline salt (benazolin-salts), bencarbazone (bencarbazone), benfururalin (benefin), benfurasete, bensulfuron, bensulfuron, bensulfuronmethyl (bensulfuron), bensulfuronmethyl (bensulfuron) Ventazon, bentazone, bentazone sodium (bentazone-sodium), bentranil, benzadox, benzadox-ammonium, benzadox-ammonium, benzadox-ammonium, benzadox-ammonium, benzfendizone Ammonium (benzobicylon), benzophenap (benzophenap), benzofluor (benzofluor), benzoylprop (benzoylrop), benzoylprop-ethyl (benzoylrop-ethyl), benzthiazlon (benzhiacuron) Bilanafos, bialaphos), bilanaphos-sodium, binapacryl, bispyribac, bispyribac-sodium, bispyribac-sodium Bixlozone, borax, bromacil, bromacil-salts, bromobonyl, bromobude, bromophenoxym, bromopenoxym, bromopenoxym, bromoxy, bromoxy, bromoxy, bromoxy , Bromoxynil-potassium, bromoxynil-esters, butachlor, butafenacil, butamiphos, butabiphos, butenachlor, butenachlor, butenachlor, butenachlor ), Butiuron, butroxydim, buturon, butylate, cafenstrole, calcium cyanamide, calcium calcium chlorate, calcium chlorate, calcium chlorate (Carbasulum), carbetamide, carboxazole, carfentrazone, carfentrazone-ester, CDEA, CEPC, chromothylopen (chlomethoxyl). chloramben, salt of chloramben (chloramben-salts), chloramben-methyl, chloramben-methylammonium, chloranocryl (chloranocryl, dichryl), chloracholyl, dichryl Chlorazifop-propargyl, chlorazine, chlorbromuron, chlorbufam, BIPC, chloreturon ), Chlorophenac (fenac), salt of chlorophenac (chlorfenac-salts), chlorophenprop, chlorphenprop-methyl, chloroflulazole, chloroflurazol. Chloroflurenol, chloroflurenol-methyl, chloridazon, PAC, pyrazon, chlorimuron, chlorimuron, chlorimuron-ester, chlorimuron-ester, chlornidin, chlornyl, chlornyl. Acetic acid (chloroacetic acid, monochloroacetic acid), sodium chloroacetate (sodium chloroaceticate, SMA), chlorotoluron, chloroxuron, chloroxuron, chloroxynyl, chloroprocarbol, chloroprocarbol Chloropharm, IPC, chlorosulfuron, chlorothal, TCTP, chlorothal-esters, chlorothiamid, DCBN, chlorothiamid, DCBN, chlorothiamid, DCBN, chlorothiamid, DCBN, chlorothiamid, DCBN, chlorothiamid, DCBN, chlorothiamid, DCBN ), Cisanylide, clacyphos, cletodim, cliodinate, clodinaphop, clodinahop propargyl (clodinafopo-chloro), chloroacetic acid, chloroacetic acid, chloroacetic acid, chloroacetic acid, chloroacetic acid, chloroacetic acid, chloroacetic acid, chloroacetic acid, chloroacetic acid, chloroacetic acid, chloroacetic acid. , Chromazone, chromeprop, cloprop, cloproxydim, clopyrlide, clopyralidome Chill (clopyrlide-methyl), salt of clopyralid (clopyrlide-salts), chloranthrum, chloransulum-methyl, copper sulphate (divalent) (copper sulfate), CPMF, CPPC, cresol, CPPC, cresol , Cresol, cumyllon, cyanatrin, cyanamide, cyanazine, cycloate, cyclopyranyl, cyclopyrimolate, cyclopyrimolate, cyclopyrmolate, cyclopyrmolate, cyanamide, cyanamide, cyanamide, cyanamide, cyanamide, cyanamide, cyclopyryl, cyanamide, cyanamide. ), Cycloxydim, cyclulon, COMU, cyhalohop, cyhalohop-butyl, cyperquat, cypercoat, cyperlacyl, cyperzine, cyperqat (Cyprazole), cypromid, dimuron, dymron, dalapon, dalapon-salts, dazomet, dazomet sodium, dazomet-de-sol, dazomet-so. Fam (desmedipham), desmethrin, di-allate, dicamba, MDBA, dicamba-salts, dicamba-ester
s), diclobenil (DBN), dichlorolaurea (DCU), dichloromate, orthodichlorobenzene (DCB), dichlorprop (diclorpro), dicloplol , Dichlorprop-esters, Dichlorprop-P, Dichlorprop-P-salts, Dichlorprop-P-esters, Dichlorprop-P-esters, Dichlorprop-P-salts, Dichlorprop-P-esters Diclohop, diclohop-methyl, diclohop-P, diclohop-P-methyl, dicloslum, dimethyl coat, dimethyl disulfide, dimethyl disulfide, dimethyl disulfide, dimethyl disulfide, dimethyl disulfide, dimethyl disulfide, dimethyl disulfide, dimethyl disulfide, dimethyl disulfide, dimethyl disulfide, dimethyl disulfide, dimethyl disulfide, dimethyl dim ), Diethatiyl, diethatyl-ester, diphenopenten, diphenopenten-ethyl, diphenoxyl, diphenoxyl-ester, diphenoxyl-ester, diphenoxyl-ester, diphenoxyl-ester, diphenoxyl-ester ), Diflufenican, diflufenzopyr, diflufenzopyr-sodium, dimefuron, dimefuron, dimepiperate, dimepiperate, dimepiperate, dimepiperate, dimepiperete (Dimethametrin), dimethenamide, dimethenamide-p, dimexano, dimidazon, dimethyl disulfide (dimethyl disulfide) dimethyl disulfide, dimethyl disulfide, dimethyl disulfide, dimethyl disulfide, dimethyl disulfide, dimethyl disulfide Prop), dinoseb, dinoseb (DNBP), dinoseb salt (dinoseb-salts), dinoseb ester (dinoseb-esters), dinoseb ester, dinoseb dinoseb, dinoseb salt (dinoseb) (Dinoseb-esters), diphenamide, dipropalin, dipropetrin, diquqt, diquat dibromid, diquqt dibromide, disolu, disul -Sodium, dithiopyr, diuron, DCMU, DMPA, DNOC, DNOC salts (DNOC-salts), EBEP, egrinazine, egrinazine ethyl (eglinaze-ester) ), Endotal-salts, epronaz, EPTC, epiriphenacil, erbon, esprocarb, esterol, ester, ester, ester, ester, ester, ester, ester. ester sulfuron, ester sulfuron-methyl, ester chlor, esterimuron, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester ethoxyphen-ester, ethoxysulfuron, ethinophen, etnipromid, etobenzanid, EXD, phenashlam, fenoseb, phenoseb, phenoseb, phenoseb, phenoseb Dinoseb salts (fenorop-salts), phenoprop-esters, phenoxaprop (fenoxa)
Prop), phenoxaprop-ester, phenoxaprop-p, phenoxaprop-ethyl, phenoxasulfone, phenoxasulfone, fenquinotrione. Fenteracol, fenthiaprop, fenthiaprop-ester, fentrazamide, divalent iron sulfate (ferrous sulfate), phenuron, phenylonTCA. ), Benzyl, Ester of Benzyl (flampl-esters), Ester of Benzyl M (fragrop-M), Ester of Benzyl M-esters, Frazasulfuron, floraslum ), Florpyrauxifen, floryrauxifen-benzyl, fluazihop, fluazihop-esters, fulazihop P (fluazifo), fluazihop P (fluazip), fluorpyrauxifen, fluorpyrauxifen, fluorpyrauxifen. p-esters), fluazolate, flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchlorolulfuron, fluchloralin, fluphenylacfuren, fluphenylacfuren (Flufenpyr), flufenpyr-ester, flumethsulum, flumesin, fulmicrolac, fluorac-pentyl, flumiclolac-pentyl, flumioxadin (fluor) ), Fluoroesteron, Fluoro Glufosinate, fluoroglycofen, fluoroglycofen, fluoroglycofen-ester, fluoromidine, fluoronitrophen, CFNP, fluoronitoroven, CFNP, fluorophsinate, fluorophsinate, glufosinate, glufosinate, glufosinate, glufosinate, glufosinate, glufosinate. , Flupropanate, ester, flupropanate-sodium, flupyrsulfuron, flupyrsulfuron-methyl, flupyrsulfuron-methyl, flupursulfuron sodium (flupur) Methylsodium (flupyrsulfuron-methyl-sodium), fluridone, flurochloridone, fluroxypyr, ester of glufosinate (fluroxypyr-esters), glufosinate, glufosinate, glufosinate, glufosinate, glufosinate, glufosinate, glufosinate, glufosinate. (Fluthiacet-methyl), fomesafen, fomesafen-sodium, foramsulfuron, fosamine, fosamine-amnium, phosamine-ammonium (Glufosinate), glufosinate salt (glufosinate-salts), glufosinate P (glufosinate-P), glufosinate P salt (glufosinate-P-salts), glyphosate, glyphosate, glyphosate, glyphosate, glyphosate. (Halauxifen), halouxifenmethyl (halauxifen-methyl), halosafen, halosulfuron, halosulfuron-methyl, haloxy Gin (haloxydine), haloxyhop, sodium haloxyhop-sodium, ester of haloxyhop-esters, haloxyhop-P, ester of haloxyhop P, ester of haloxyhop P, halox Mycin (herbimycin), hexachloroacetone (HCA), hexadinone (hexazinone), imazamethabenz, imazamethabenz methyl (imazamethabenza-methyl), imazamezamimax (imazamezabenza-methyl), imazaminox (Imazapic), imazapic-ammonium, imazapyr, imazapyr-isopropylammonium, imazaquin, ioxynil, ioxynil, ioxynil, ioxynil, ioxynil, ioxynil, ioxynil, ioxynil, ioxynil, ioxynil, ioxynil, ioxynil, ioxynil, ioxynil, ioxynil, ioxynil, ioxynil, ioxynil, ioxynil, ioxynil, ioxynil, ioxynil , Imazetapyr, imazetapyr-ammonium, imazosulfuron, indanofan, indanofan, indazifram, ioxynil, ioxynil, ioxynil, ioxynil, ioxynil, ioxynil, ioxynil, ioxynil, ioxynil, ioxynil, ioxynil, ioxynil, ioxynil, ioxynil, ioxynil, ioxynil, ioxynil, ioxynil, ioxynil, ioxynil, ioxynil, ioxynil, ioxynil, ioxynil, ioxynil sodium), iodosulfuron-methyl, iodosulfuron-methyl-sodium, yofensulfuron, iofensulfuron, iofensulfuron-oxynil ioxynil ioxynil ioxynil ioxynil ioxynil ioxynil ioxynil ioxynil ioxynil ioxynil ioxynil ioxynil ioxynil Salts (ioxynil-salts), esters of ioxynil (ioxynil-esters), ipazine (ipazine), ipfencarbazone (ipfencarbazone), iprymidam, isocarbamide ), Isocil, isoprocil, isomethiodin, isonoruron, isoporinate, isopropolin, isoproturon, isoproturon, isouron, isouron, isouron. Toll (isoxachlortole), isoxaflutole (isoxaflutole), isoxapyrihop, carbutylate, ketospiradox, ketospiradox potassium (ketospiradox) colacto, ketospiradox (Lancotrione), lancotrione-sodium, lenacil, linuron, MCPA, MCPA salts (MCPA-salts), MCPA esters (MCPA-esters), MCPB, MCPB salts (MCPB) -Salts), ester of MCPB (MCPB-esters), mecoprop (mecoprop, MCPP), salt of mecoprop (mecoplop-salts), ester of mecoprop-esters, mecoprop-P, salt of mecoprop P (Mecoprop-P-salts), ester of mecoplop P (mecop-P-esters), medinotelb, medinotelb acetate, mefenacet, mefluidide, mefluide, mefluoride Salts), mesoprazine, mesosulfuron, mesosulfuron-methyl, methotrione, metam, carbam, metam, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester, ester (Metamitron), metazachlor (methazachlor), metazosulfuron (methazosulfuron)
), Methylurazon, methabenzuthiazuron, methylnzuron, metalpropalin, methazole, methylobencarb, methylmethonemethone, methylmethyl, methyl group, methyl group, methyl group, methyl groupe methoprotrin, methoxyphenone, methiopyrisulfuron, methiozolin, methyl azide, methyl bromide, methyl dye, methyl dye, methyl dye, methyl dye, methyl dye, methyl dye, methyl dye, methyl dye, methyl dye, methyl dye. , Methyl isothiocyanate, methyl isothiocyanate, methyl benzuron, metobromuron, metrachlor, S-metholachlor, S-metholachlor, methyloxuron, metosulam, methylisothiocyanate Methosulfuron, Methosulfuron Methyl (metsulfuron-methyl), Molinate, monalide, monisouron, monolinuron, monosulfuron, monosulfuron, monosulfuron, monosulfuron, monosulfuron. monuron, CMU), monuron TCA (monuron-TCA), morphamcoat (morphamquat), morphamcoat dichloride, naproanilide, naproanilide, napropamide, napropamide, napropamide, napropamide, napropamide, napropamide. , NPA), naptalam-sodium, nebulon, nicosulfuron, nipyraclophen ), Nitralin, nitrofen, NIP, niclofen, nitrofluorfen, norflurazon, noruron, norea, OCH, oleic acid, oleic acid, oleic acid, oleic acid, oleic acid, paraquat, paraquat, paraquat, paraquat, paraquat, paraquat, paraquat, paraquat, paraquat, paraquat, paraquat. Sulfamron, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxapyrazon, oxapyrazone salt (oxapyrazon-salts), oxasulofon, oxasulofuron (Oxyfluorfen), paraquaturon, paraquat, paraquat dichloride, paraquat dimethylsulfate, pebulate, pebulate, pebulate, pebulate, pebulate.
acid), pendimethalin, penoxyslam, pentachlorophenol, sodium pentachlorophenoxide, pentachlorophenol laurate, pentachlorophenolollane, pentachlorophenylate
CMMP), pentoxazone, perfluidone, petoxamide, phenisopham, phenmedipham, phenmedifam, phenmedifamethyl, phenmedipharmyl, phenmedipharmyl ), Picloram-salts, picloram-esters, picolinaphen, pinoxaden, piperophos, potassium azide (potassium cyanate), potassium azide (potassium cyanate). , Pretilacroll, primisulfuron, primisulfuron-methyl, procyazine, prodiamine, profluazole, profluazole, profluazole, proflulazol. , Propazineazine, Propazineethyl, Propazine-ester, Prometon, Promethrin, Prometrine, Propazine, Propazine, Propazine, Propazine, Propazine, Propazine, Propazine, Propazine, Propazine, Propazine, Propazine, Propazine, Propazine, Propazine Propazine, profam, propisochlor, propoxycarbazone, propoxycarbazone-sodium, propoxycarbazone-sodium, propylsulfurone-sodium, propylsulfurone (propazine), propoxycarbazone-sodium, propoxycarbazone-sodium Prosulfalin, prosulfocarb, prosulfuron, proxan (IPX), proxan sodium (proxan-osodium), prinachlor (pryn) achlor, pyranone, pyraclonil, pyraflufen, pyraflufen-ester, pyrasulfotole, pyrazolfootole, pyrazolynate, pyrazolynate, pyrazolonate, pyrazolonate, pyrazolofolz Ethyl (pyrazosulfuron-ester), pyrazoxyfen, pyribambenza-isopropyl, pyribambenza-propyl, pyribambenz-propyl, pyribombenz-propyl, pyribombenz-propyl, pyribombenz ), Pyridate, pyriftalid, pyriminobac, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac, pyrithiobac sodium, pyrithiobac sodium, pyrithiobac Sasulfon, pyroxsulum, quinchlorac, quinchlorac-dimesternium, quinchlorac-methyl, quinchlorac-methyl, quinchlorac-methyl, quinclolac-methyl, quinolumin (Quinonamid), quizalofop, ester of quizalofop-esters, quizalofop-P, ester of quizalofop P (quizalofop-P-esters), sulfuron, sulfuron (Saflufenacil), sebutylazine, secbumethon, setoxydim, siduron, simazin e, CAT), simeton, simetrin, simetrine, sodium azide, sodium chlorate, sulfotrione, sulfarate, sulfate (Sulfentrazone), sulfometuron, sulfometuron-methyl, sulfosulfuron, sulfuric acid, sulglycapine (su)
lglycapin, sweep (swep, MCC), tabron, TCA (trichloloacetic acid), TCA salt (TCA-salts), TCA ester (TCA-ester), tebuthiuron, tebuthiuron, tebuthiuron, tebuthiuron Tebuthiuronite, tembotrione, tepraloxydim, terbacill, terbucarb, terbutol, MPMC, terbuthiuron, terbuthiuron, terbuthiuron, terbuthiuron, terbuthiuron, terbuthiuron (Terbutrin), tetflupyrolimet, tetrafluron, tenylchlor, thiazafluron, thiazopyr, thiazopyr, thiazodizan, thidiajimin, thiaziondiazion. Methyl (thiencarbazone-methyl), tebuthiuron (thifensulfuron), tebuthiuron-methyl (thifensulfuron-methyl), thiobencarb, benthiocarb, triclopyratioribrate, tyafenacil (tiafenacil) ), Topramezone, tralcoxydim, triafamone, triallate, tri-allate, triasulfuron, triclopyrone, triclopyron, triaziflam -Methyl), triclopyr, triclopyr, triclopyr-salts, triclopyr-este rs), tridiphane, trietazine, trifloxysulfuron, trifloxysulfuron-sodium, trifludysulfuron-sodium, trifludimoxazine, trifluylflulyfurin (Triflufuron), triflusulfuron-methyl, trihop, trihop-methyl, triphopsime, trihydroxytriazine, trihydroxytriazine, trihydroxytriazine, trihydroxytriazine, trihydroxytriazine, trihydroxytriazine, trihydroxytriazine, trihydroxytriazine, trihydroxytriazine. Dan (tripropindan), tritac, tritosulfuron, vernate, xylachlor, 6-{(difluoromethyl) thio} -N2, N4-diisopropyl-1,3,5 -Triazine-2,4-diamine (CAS 103427-73-2), (R) -2-[{7- (2-chloro-4- (trifluoromethyl) phenoxy) naphthalene-2-yl} oxy] propane Methyl acid (CAS 10305-25-0), propan-2-one O- (12H-dibenzo [d, g] [1,3] dioxosin-6-carbonyl) oxime (CAS 503819-68-9), [{ (2- (N-Methylmethylsulfonamide) -2-oxoethyl) amino} methyl] phosphonic acid (CAS 98565-18-5), 2-[{2- (4-((6-chloroquinoxalin-2-yl) ) Oxy) Phenoxy) Propanoyl} Oxy] -3-methyl-3-butenoate ethyl (CAS 11919232-79-2), 2- (3,7-dichloroquinolin-8-carbonyl) -3-hydroxy-2-cyclohexene -1-one (CAS 1350901-36-8), O- (2,4-dimethyl-6-nitrophenyl) O-methylisopropylphosphoramidothioate (CAS 189517-75-7), 5- [N- { (4,6-dimethylpyrimidine-2-yl) carbamoyl} sulfamoyl] -1- (pyridin-2-yl) -1H-pyrazo Methyl ru-4-carboxylate (CAS 104770-29-8), 4- [2-chloro-3-{(3,5-dimethyl-1H-pyrazol-1-yl) methyl} -4- (methylsulfonyl) Benzoyl] -1,3-dimethyl-1H-pyrazol-5-yl 1,3-dimethyl-1H-pyrazol-4-carboxylate (CAS 191613-97-2), 4- [2-chloro-4- (methyl) Sulfonyl) -3-{(2,2,2-trifluoroethoxy) methyl} benzoyl] -1-ethyl-1H-pyrazol-5-yl 1,3-dimethyl-1H-pyrazol-4-carboxylate (CAS 19992017) -55-6), 1- {2-chloro-3- (3-cyclopropyl-5-hydroxy-1-methyl-1H-pyrazol-4-carbonyl) -6- (trifluoromethyl) phenyl} piperidine-2 -On (CAS 185592-45-1), 1,3-dimethyl-4- {2- (methylsulfonyl) -4- (trifluoromethyl) benzoyl} -1H-pyrazol-5-yl 1,3-dimethyl- 1H-pyrazole-4-carboxylate (CAS 1622908-18-2), 2-methyl-N- (5-methyl-1,3,4-oxadiazol-2-yl) -3- (methylsulfonyl)- 4- (Trifluoromethyl) benzamide (CAS)
140904-50-8), 2-chloro-N- (1-methyl-1H-tetrazol-5-yl) -3- (methylthio) -4- (trifluoromethyl) benzamide (CAS 1361139-71-0), 2-Chloro-N- (1-methyl-1H-tetrazole-5-yl) -3- (methylsulfonyl) -4- (trifluoromethyl) benzamide (CAS 1361139-73-2), 4- (4-fluoro Phenyl) -6- (2-hydroxy-6-oxo-1-cyclohexene-1-carbonyl) -2-methyl-1,2,4-triazine-3,5 (2H, 4H) -dione (CAS 13538370-34) -4), 4-Amino-3-chloro-5-fluoro-6- (7-fluoro-1H-indol-6-yl) picolinic acid (CAS 1628702-28-2), 2-propin-1-yl 4) -Amino-3-chloro-5-fluoro-6- (7-fluoro-1H-indol-6-yl) picolinic acid (CAS 2251111-17-6), cyanomethyl 4-amino-3-chloro-5-fluoro- 6- (7-Fluoro-1H-Indol-6-yl) picolinic acid (CAS 2251111-18-7), 2- (3,4-dimethoxyphenyl) -4- (2-hydroxy-6-oxocyclo-1-) Hexen-1-carbonyl) -6-methylpyridazine-3 (2H) -one (CAS 2138855-12-4), 3- (2,6-dimethylphenyl) -6- (2-hydroxy-6-oxocyclo-1) -Hexen-1-carbonyl) -1-methylquinazoline-2,4 (1H, 3H) -dione (CAS 1639426-14-4), F4050 (test name), F9960 (test name), OK-701 (test name) ) And SL-1201 (test name) and the like. These components can be used alone or in combination of two or more, and the ratio when mixed can be freely selected.

Examples of the phytotoxicity reducing agent include benoxacor, BPCMS (CSB), cloquintocet, cloquintocet-mexyl, cumyllon, ciometrinyl, and cyometrinyl. (Cyprosulfamide), dimuron, dymron, dichlormid, dicyclonon, dicyclonon, dietholate, dimetholate, dimepiperate, dimepiperofene, dimepiperone, dimepiperone, dimepiperone fenchlorazole-ethyl, fenchlorim, flurazole, fluxophenim, furilazole, hexim, hexim, isoxadiphen (isoxadiphen), isoxadiphen (isoxadiphen), isoxadiphen (isoxadiphen) mecoprop), mefenpyr, mefenpyr-diethyl, mephenate, metcamife
n), methoxyphenone, 1,8-naphthalic anhydride (NA), octamethylenediamine (octamethylene-diamine), oxabetrinil, 4- (dichloroacetyl) -1-oxa-4. -Azaspiro [4.5] decane (AD67, MON4660), 4-carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid (CL304415), 2,2-dichloro-N- [2-oxo- 2- (Propenylamino) ethyl] -N-2-propenylacetamide (DKA-24), 2- (dichloromethyl) -2-methyl-1,3-dioxolane (MG191), 2-propenyl 1-oxa-4- Azaspiro [4,5] decane-4-carbodithioate (MG838), (3-dichloroacetyl-5- (2-furyl) -2,2-dimethyloxazoxidine) (MON13900), (N-allyl-N) -[(1,3-Dioxolan-2-yl) methyl] dichloroacetamide (PPG-1292), 3- (dichloroacetyl) -2,2-dimethyl-1,3-oxazolidine (R28725), 3- (dichloroacetyl) ) -2,2,5-trimethyl-1,3-oxazolidine (R29148), 1-dichloroacetylazepan (TI-35) and the like. These components are used alone or in combination of two or more. The ratio for mixing can be freely selected.

The amount of the compound of the present invention to be applied varies depending on the application situation, application time, application method, cultivated crop, etc., but generally, the amount of the active ingredient is appropriately about 0.005 to 50 kg per hectare (ha).

Next, a formulation example of the preparation when the compound of the present invention is used is shown. However, the formulation examples of the present invention are not limited to these. In the following formulation example, "part" means a part by weight.

Wettable powder 0.1 to 80 parts of the present invention Solid carrier 5 to 98.9 parts Surfactant 1 to 10 parts Others 0 to 5 parts Other examples include anti-caking agents and anti-decomposition agents.

Emulsion Compound of the present invention 0.1 to 30 parts Liquid carrier 45 to 95 parts Surfactant 4.9 to 15 parts Others 0 to 10 parts Other examples include spreading agents and decomposition inhibitors.

Flowable agent 0.1 to 70 parts of the compound of the present invention Liquid carrier 15 to 98.89 parts Surfactant 1 to 12 parts Others 0.01 to 30 parts Other examples include antifreeze agents and thickeners. Be done.

Dry flowable agent 0.1 to 90 parts of the compound of the present invention Solid carrier 0 to 98.9 parts Surfactant 1 to 20 parts Others 0 to 10 parts Others include, for example, a binder, a decomposition inhibitor and the like. ..

Liquids Compounds of the present invention 0.01 to 70 parts Liquid carriers 20 to 99.99 parts Others 0 to 10 parts Other examples include antifreeze agents and spreading agents.

Granules 0.01 to 80 parts of the compound of the present invention Solid carrier 10 to 99.99 parts Others 0 to 10 parts Other examples thereof include binders and decomposition inhibitors.

Powders Compounds of the present invention 0.01 to 30 parts Solid carrier 65 to 99.99 parts Others 0 to 10 parts Other examples include anti-drift agents and anti-decomposition agents.

When using, the above preparation is sprayed as it is or diluted 1 to 10,000 times with water.

Examples of preparations Next, examples of pesticide preparations containing the compound of the present invention as an active ingredient are shown, but the present invention is not limited to these. In the following formulation example, "part" means a part by weight.

[Formulation Example 1] Wettable Compound No. 1-1-304 20 parts Pyrophyllite 76 parts Solpol 5039 2 parts (Anionic surfactant: Toho Chemical Industry Co., Ltd. trade name)
Carplex # 80 Part 2 (Synthetic hydrous silicic acid: Shionogi Pharmaceutical Co., Ltd. trade name)
The above is uniformly mixed and pulverized to obtain a wettable powder.

[Formulation Example 2] Milk The compound No. 1 of the present invention. 1-1-304 5 parts Xylene 75 parts N-methylpyrrolidone 15 parts Solpol 2680 5 parts (Anionic surfactant: Toho Chemical Industry Co., Ltd. trade name)
The above is uniformly mixed to obtain an emulsion.

[Formulation Example 3] Flowable agent Compound No. 3 of the present invention. 1-1-304 25 parts Agrisol S-710 10 parts (Nonionic surfactant: Kao Corporation trade name)
Lunox 1000C 0.5 part (Anionic surfactant: Toho Chemical Industry Co., Ltd. trade name)
After uniformly mixing 0.02 parts of xanthan gum and 64.48 parts of water or more, wet pulverization is performed to obtain a flowable agent.

[Formulation Example 4] Dry flowable agent Compound No. 4 of the present invention. 1-1-304 75 parts Hytenol NE-15 5 parts (anionic surfactant: Daiichi Kogyo Seiyaku Co., Ltd. trade name)
Vanillex N 10 parts (anionic surfactant: Nippon Paper Co., Ltd. trade name)
Carplex # 80 10 parts (Synthetic hydrous silicic acid: Shionogi Pharmaceutical Co., Ltd. trade name)
After uniformly mixing and crushing the above, a small amount of water is added, stirred and mixed and kneaded, granulated by an extrusion type granulator, and dried to obtain a dry flowable agent.

[Formulation Example 5] Granules Compound No. 5 of the present invention. 1-1-304 1 part Bentonite 55 parts Talc 44 parts After uniformly mixing and crushing, add a small amount of water, stir, mix and knead, granulate with an extrusion granulator, dry and mix with granules. To do.

Hereinafter, the present invention will be described in more detail by specifically describing synthetic examples and test examples of the heterocyclic compound represented by the formula (1) as examples, but the present invention is limited thereto. It's not something.

First, synthetic examples and reference examples of the compound according to the present invention will be described.
For the medium pressure preparative liquid chromatography described in the synthesis example and the reference example, Yamazen Corporation medium pressure preparative apparatus; YFLC-Wprep (flow velocity 18 ml / min, silica gel 40 μm column) was used.
The proton nuclear magnetic resonance spectrum described below (hereinafter referred to as ¹ H-NMR) was measured at 300 MHz (JNM-ECX300 or JNM-ECP300, manufactured by JEOL Ltd.). Deuterated chloroform or deuterated dimethyl sulfoxide was used as the measurement solvent. When deuterated chloroform was used as the solvent, tetramethylsilane was used as the reference substance.
¹ The symbols in the chemical shift value of ¹ H-NMR have the following meanings.
s: singlet, brs: broad singlet, d: doublet, dd: double doublet, t: triplet, q: quartet, m: multiplet Also, regarding signals that can be analyzed when two or more isomers are present. Each chemical shift value is indicated by "and".

Synthesis example [Synthesis example 1]
Ethyl (1- (3-((isopropylsulfonyl) methyl) -N- (5-methyl-1,3,4-oxadiazole-2-yl) -5- (trifluoromethyl)-[1,2, 4] Synthesis of triazolo [4,3-a] pyridin-8-carboxamide) ethyl) carbonate (Compound No. 1-1-304 of the present invention) 3-((isopropylsulfonyl) methyl) -N- (5-methyl- 1,3,4-Oxadiazole-2-yl) -5- (trifluoromethyl)-[1,2,4] triazolo [4,3-a] Pyridine-8-carboxamide 1.0 g to 40 ml acetonitrile After lysis, 720 mg of 1-chlorodiethyl carbonate, 660 mg of potassium carbonate and 780 mg of potassium iodide were added at room temperature. After completion of the addition, the mixture was stirred under heating under reflux for 5 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. 20 ml of water was added to the obtained residue, and the mixture was extracted with ethyl acetate (20 ml x 2 times). The obtained organic layer was dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue is eluted with n-hexane-ethyl acetate-methanol [gradient of 50:50: 0-0: 100: 0-0: 90: 10 (volume ratio, the same applies hereinafter)]. Purification by medium pressure preparative liquid chromatography gave 283 mg of the desired product as a brown solid.
Melting point: 77-82 ° C

[Synthesis Example 2]
Ethyl (1- (3-((isopropylthio) methyl) -N- (5-methyl-1,3,4-oxadiazol-2-yl) -5- (trifluoromethyl)-[1,2, 4] Synthesis of triazolo [4,3-a] pyridin-8-carboxamide) ethyl) carbonate (Compound No. 1-1-524 of the present invention) 3-((Isopropylthio) methyl) -N- (5-methyl- 1,3,4-oxadiazol-2-yl) -5- (trifluoromethyl)-[1,2,4] triazolo [4,3-a] pyridine-8-carboxamide 250 mg was dissolved in 10 ml of acetonitrile. , 220 mg of 1-chlorodiethyl carbonate, 200 mg of potassium carbonate and 240 mg of potassium iodide were added at room temperature. After completion of the addition, the mixture was stirred under heating under reflux for 3.5 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. 10 ml of water was added to the obtained residue, and the mixture was extracted with chloroform (10 ml × 2 times). The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and then 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 20:80 to 0: 100) and then chloroform-methanol (99: 1). 192 mg of the product was obtained as a red resinous solid.
¹ H-NMR (CDCl ₃ ): δ8.08 (d, J = 7.2Hz, 1H), 7.44 (d, J = 7.2Hz, 1H), 6.82 (q, J = 6.3Hz, 1H), 4.31 (s , 2H), 4.18 (q, J = 6.9Hz, 2H), 3.15-3.00 (m, 1H), 2.42 (s, 3H), 1.78 (d, J = 6.0Hz, 3H), 1.26 (t, J = 7.2Hz, 3H), 1.25 (d, J = 7.2Hz, 6H).

[Synthesis Example 3]
N- (3,5-dimethyl-1,3,4-oxadiazol-2 (3H) -iriden) -3-((isopropylsulfonyl) methyl) -5- (trifluoromethyl)-[1,2, 4] Synthesis of triazolo [4,3-a] pyridine-8-carboxamide (Compound No. 1-2-221 of the present invention) 3-((Isopropylsulfonyl) methyl) -5- (trifluoromethyl)-[1, 2,4] To a mixed solution of 400 mg of triazolo [4,3-a] pyridine-8-carboxylic acid and 20 ml of dichloromethane, 289 mg of oxalyl dichloride and 30 mg of N, N-dimethylformamide were added at room temperature. After completion of the addition, the mixture was stirred at room temperature for 2 hours. After the stirring is completed, the solvent is distilled off from the reaction mixture under reduced pressure to obtain 3-((isopropylsulfonyl) methyl) -5- (trifluoromethyl)-[1,2,4] triazolo [4, 3-a] A crude product of pyridine-8-carboxylic acid chloride was obtained. The obtained crude product of 3-((isopropylsulfonyl) methyl) -5- (trifluoromethyl)-[1,2,4] triazolo [4,3-a] pyridine-8-carboxylic acid chloride was separately separated. It was added to a mixed solution of 329 mg of 3,5-dimethyl-1,3,4-oxadiazole-2 (3H) -imine hydroiodide and 20 ml of dichloromethane prepared in a container at room temperature. After completion of the addition, 253 mg of triethylamine was added to the mixture at room temperature. After completion of the addition, the mixture was stirred at room temperature for 1 hour. After completion of the reaction, 10 ml of a saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, and the mixture was extracted with chloroform (10 ml × 2 times). The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and then 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 10:90 to 0: 100) to obtain 230 mg of the target product as a resinous solid. ..
¹ H-NMR (CDCl ₃ ): δ8.06 (d, J = 7.2Hz, 1H), 7.54 (d, J = 7.2Hz, 1H), 5.00 (s, 2H), 3.96-3.80 (m, 1H) , 3.69 (s, 3H), 2.48 (s, 3H), 1.46 (d, J = 6.9Hz, 6H).

[Synthesis Example 4]
N- (3-benzyl-5-methyl-1,3,4-oxadiazol-2 (3H) -iriden) -3-((isopropylsulfonyl) methyl) -5- (trifluoromethyl)-[1, 2,4] Synthesis of triazolo [4,3-a] pyridine-8-carboxamide (Compound No. 1-2-274 of the present invention) 3-((Isopropylsulfonyl) methyl) -5- (trifluoromethyl)-[ 1,2,4] To a mixed solution of 400 mg of triazolo [4,3-a] pyridine-8-carboxylic acid and 20 ml of dichloromethane, 289 mg of oxalyl dichloride and 30 mg of N, N-dimethylformamide were added at room temperature. After completion of the addition, the mixture was stirred at room temperature for 2 hours. After the stirring is completed, the solvent is distilled off from the reaction mixture under reduced pressure to obtain 3-((isopropylsulfonyl) methyl) -5- (trifluoromethyl)-[1,2,4] triazolo [4, 3-a] A crude product of pyridine-8-carboxylic acid chloride was obtained. The obtained crude product of 3-((isopropylsulfonyl) methyl) -5- (trifluoromethyl)-[1,2,4] triazolo [4,3-a] pyridine-8-carboxylic acid chloride was separately separated. It was added to a mixed solution of 370 mg of 3-benzyl-5-methyl-1,3,4-oxadiazole-2 (3H) -imine hydrobromide and 20 ml of dichloromethane prepared in a container at room temperature. After completion of the addition, 253 mg of triethylamine was added to the mixture at room temperature. After completion of the addition, the mixture was stirred at room temperature for 16 hours. After completion of the reaction, 10 ml of a saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, and the mixture was extracted with chloroform (10 ml × 2 times). The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and then 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 20:80 to 0: 100) to obtain 345 mg of the target product as a resinous solid. ..
¹ H-NMR (CDCl ₃ ): δ8.06 (d, J = 7.2Hz, 1H), 7.55 (d, J = 7.2Hz, 1H), 7.49-7.30 (m, 5H), 5.17 (s, 2H) , 5.01 (s, 2H), 3.96-3.80 (m, 1H), 2.44 (s, 3H), 1.46 (d, J = 6.9Hz, 6H).

[Synthesis Example 5]
Ethyl (3-isopropyl-5- (trifluoromethyl)-[1,2,4] triazolo [4,3-a] pyridine-8-carbonyl) (5-methyl-1,3,4-oxadiazole- 2-Il) carbamate (Compound No. 1-1-882 of the present invention) and ethyl 2-((3-isopropyl-5- (trifluoromethyl)-[1,2,4] triazolo [4,3-a]] Synthesis of pyridine-8-carbonyl) imino) -5-methyl-1,3,4-oxadiazol-3 (2H) -carboxylate (Compound No. 1-2-882 of the present invention) 3-isopropyl-N- (5-Methyl-1,3,4-oxadiazol-2-yl) -5- (trifluoromethyl)-[1,2,4] triazolo [4,3-a] pyridine-8-carboxamide 120 mg It was dissolved in 3 ml of dichloromethane, and 38 mg of triethylamine and 40 mg of ethyl chlorostate were added under ice-cooling. After completion of the addition, the mixture was stirred under ice cooling for 30 minutes. After completion of the reaction, 10 ml of water was added to the reaction mixture, and the mixture was extracted with chloroform (5 ml × 3 times). The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and then 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 30: 70-0: 100) and ethyl (3-isopropyl-5- (tri-isopropyl-5)). Fluoromethyl)-[1,2,4] triazolo [4,3-a] pyridin-8-carbonyl) (5-methyl-1,3,4-oxadiazol-2-yl) carbamate and ethyl 2- ( (3-Isopropyl-5- (trifluoromethyl)-[1,2,4] triazolo [4,3-a] pyridine-8-carbonyl)
67 mg of a mixture of imino) -5-methyl-1,3,4-oxadiazole-3 (2H) -carboxylate was obtained as a resinous solid. No. 1-1-882 and No. The mixing ratio of 1-2-882 was calculated by ^{1 1} H-NMR, and the ratio was 1-1-882: 1-2-882 = 43: 57, or 1-1-882: 1-2-882 = 57:43.
^{1 1} H-NMR (CDCl ₃ ): δ8.23 and 8.06 (d, J = 7.5Hz, 1H), 7.52 and 7.44 (d, J = 7.2Hz, 1H), 4.48-4.34 (m, 2H), 3.73- 3.58 (m, 1H), 2.38 and 3.41 (s, 3H), 1.53 and 1.50 (d, J = 6.6Hz, 6H), 1.35 (t, J = 7.5Hz, 3H).

[Reference Example 1]
Synthesis of 3,5-dimethyl-1,3,4-oxadiazole-2 (3H) -imine hydroiodate 2-amino-5-methyl-1,3,4-oxadiazole 1 g and N, 1.72 g of methyl iodide was added to a mixed solution of 10 ml of N-dimethylformamide at room temperature. After completion of the addition, the mixture was stirred at room temperature for 16 hours. After completion of the reaction, 30 ml of ethyl acetate was added to the reaction mixture, and the mixture was stirred at room temperature for 1 hour. After completion of stirring, the solid precipitated in the reaction mixture was filtered off by filtration. The obtained solid was washed with ethyl acetate to obtain 1.1 g of the desired product as a white solid.
¹ H-NMR (DMSO-d6): δ9.89 (brs, 2H), 3.54 (s, 3H), 2.42 (s, 3H).

[Reference example 2]
Synthesis of 3-benzyl-5-methyl-1,3,4-oxadiazole-2 (3H) -imine hydrobromide 2-amino-5-methyl-1,3,4-oxadiazole 1 g and 2.07 g of benzyl bromide was added to a mixed solution of 10 ml of N, N-dimethylformamide at room temperature. After completion of the addition, the mixture was stirred at room temperature for 16 hours. After completion of stirring, the mixture was stirred at 50 ° C. for 5 hours. After completion of the reaction, 30 ml of ethyl acetate was added to the reaction mixture, and the mixture was stirred at room temperature for 1 hour. After completion of stirring, the solid precipitated in the reaction mixture was filtered off by filtration. The obtained solid was washed with ethyl acetate to obtain 1.58 g of the desired product as a white solid.
¹ H-NMR (DMSO-d6): δ10.24 (brs, 2H), 7.43-7.32 (m, 5H), 5.18 (s, 2H), 2.41 (s,
3H).

[Reference Example 3]
The following compounds were synthesized in the same manner as in Reference Example 2.
Synthesis of 3-((6-chloropyridin-3-yl) methyl) -5-methyl-1,3,4-oxadiazole-2 (3H) -imine hydrochloride
¹ H-NMR (DMSO-d6): δ10.87 (brs, 2H), 8.55 (d, J = 2.4Hz, 1H), 8.00 (dd, J = 8.1, 2.4Hz, 1H), 7.57 (d, J = 8.1Hz, 1H), 5.48 (s, 2H), 2.38 (s, 3H).
Synthesis of 3-allyl-5-methyl-1,3,4-oxadiazole-2 (3H) -imine hydrobromide
¹ H-NMR (DMSO-d6): δ10.08 (brs, 2H), 5.96-5.80 (m, 1H), 5.41-5.26 (m, 2H), 4.63-4.55 (m, 2H), 2.42 (s, 3H).
Synthesis of 3- (methoxymethyl) -5-methyl-1,3,4-oxadiazole-2 (3H) -imine hydrobromide
¹ H-NMR (DMSO-d6): δ10.41 (brs, 2H), 5.30 (s, 2H), 3.39 (s, 3H), 2.44 (s, 3H).
Synthesis of 3- (cyclopropylmethyl) -5-methyl-1,3,4-oxadiazole-2 (3H) -imine hydrobromide
¹ H-NMR (DMSO-d6): δ10.02 (brs, 2H), 3.85 (d, J = 6.9Hz, 2H), 2.45 (s, 3H), 1.26-1.11 (m, 1H), 0.61-0.53 (m, 2H), 0.44-0.37 (m, 2H).
Synthesis of 1- (2-imino-5-methyl-1,3,4-oxadiazole-3 (2H) -yl) propan-2-one hydrobromide
¹ H-NMR (DMSO-d6): δ10.28 (brs, 2H), 5.21 (s, 2H), 2.49 (s, 3H), 2.25 (s, 3H).

Next, typical examples of the compounds according to the present invention are listed in Tables 1 to 3. These compounds can be synthesized based on the above synthesis example or the above-mentioned various production methods.
In the table, "=" represents a double bond, "≡" represents a triple bond, "Me" represents a methyl group, "Et" represents an ethyl group, and "Pr" represents a propyl group. , "Bu" represents a butyl group, "Hex" represents a hexyl group, "Ph" represents a phenyl group, "n-" represents a normal, "i-" represents an iso, and "c-" Represents cyclo and "t-" represents tertiary. In addition, "* 1" in the table indicates that the compound is a solid, "* 2" indicates that the compound is an oily substance or a resin, and "mp" is a melting point (unit: ° C.). Represents.
In the table, D1-1, D1-2, D1-3, D1-4, D1-5, D2, D3, D4-1, D4-2, D4-3, D4-4, D5, D6, D7, D8 -1, D8-2, D8-3, D8-4, D8-5, D9, D10, D11-1, D11-2, D11-3, D12-1, D12-2, D12-3, D13, D14 , D15, D16, D17, D18, D19-1, D19-2, D19-3 and D20 represent the following ring structures.

[Table 1]

[Table 2]

[Table 3]

^{1 H-NMR} data of the compound of the present invention shown in Tables 1 to 3 shown in Table 4.
Incidentally, proton nuclear magnetic resonance chemical shift values, using _Me 4 Si (tetramethylsilane) as the reference substance, in deuterochloroform solvent, 300 MHz; measured at (model ECX300 or ECP300, JEOL Ltd.).
The symbols in the proton nuclear magnetic resonance chemical shift value have the following meanings.
s: singlet, brs: broad singlet, d: doublet, dd: double doublet, t: triplet, q: quartet, m: multiplet

[Table 4]
――――――――――――――――――――――――――――――――――
No. ^{1 1} H NMR (CDCl ₃ , Me ₄ Si, 300 MHz).
――――――――――――――――――――――――――――――――――
1-1-744 δ8.25 (d, J = 7.5Hz, 1H), 7.55 (d, J = 7.5Hz, 1H), 6.88 (q, J = 6.3Hz, 1H), 4.98 (s, 2H), 4.28-4.16 (m, 2H), 3.39 (q, J = 7.5Hz, 2H), 2.47 (s, 3H), 1.82 (d, J = 6.0Hz, 3H), 1.47 (t, J = 7.8Hz, 3H) ), 1.30 (t, J = 7.2Hz, 3H).
1-1-881 δ7.72 (d, J = 7.8Hz, 1H), 7.53 (d, J = 7.8Hz, 1H), 4.15 (q, J = 7.2Hz, 2H), 2.78 (d, J = 7.8) Hz, 1H), 2.38 (s, 3H), 1.83 (d, J = 7.8Hz, 1H), 1.80 (s, 3H), 1.43 (t, J = 7.2Hz, 3H).
1-2-225 δ8.01 (d, J = 7.2Hz, 1H), 7.52 (d, J = 7.2Hz, 1H), 4.98 (d, J = 7.2Hz, 2H), 3.95-3.80 (m, 3H) ), 2.49 (s, 3H), 1.48 (d, J = 6.9Hz, 6H), 1.35-1.20 (m, 1H), 0.66-0.58 (m, 2H), 0.55-0.43 (m, 2H).
1-2-231 δ8.06 (d, J = 7.2Hz, 1H), 7.53 (d, J = 7.2Hz, 1H), 6.04-5.82 (m, 1H), 5.45-5.32 (m, 2H), 5.00 (s, 2H), 4.63 (dd, J = 6.3, 1.5Hz, 2H), 3.96-3.80 (m, 1H), 2.48 (s, 3H), 1.46 (d, J = 6.9Hz, 6H).
1-2-282 δ8.55 (d, J = 3.0Hz, 1H), 8.08 (d, J = 7.2Hz, 1H), 8.01 (dd, J = 8.4, 2.4Hz,
1H), 7.57 (d, J = 7.5Hz, 1H), 7.35 (d, J = 7.5Hz, 1H), 5.19 (s, 2H), 5.02 (s, 2H), 3.94-3.78 (m, 1H), 2.45 (s, 3H), 1.48 (d, J = 6.9Hz, 6H).
1-2-881 δ7.96 (d, J = 7.8Hz, 1H), 7.53 (d, J = 7.8Hz, 1H), 4.07 (q, J = 7.2Hz, 2H), 2.91 (d, J = 7.5) Hz, 1H), 2.47 (s, 3H), 1.87 (d, J = 7.8Hz, 1H), 1.85 (s, 3H), 1.44 (t, J = 7.2Hz, 3H).
――――――――――――――――――――――――――――――――――

Test Examples 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 to these.

[Test Example 1] Test of herbicidal effect by pretreatment of weeds under flooded conditions After putting alluvial soil in a Wagner pot of 1/10000 ares, water was added and mixed to obtain a flooded condition of 4 cm in depth. After seeds of Tainubier, Inuhotarui and Pontederia vaginalis were mixedly sown in the above cups, 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 dosage and treated on the water surface. The cups were placed in a greenhouse at 25 to 30 ° C. to grow plants, and after 3 weeks of chemical treatment, the effects on various plants were investigated according to the following criteria. The results are shown in Table 5.
Judgment Criteria 5 ... Weed killing rate 90% or more (almost complete death)
4… Weeding rate 70% or more and less than 90% 3… Weeding rate 40% or more and less than 70% 2… Weeding rate 20% or more and less than 40% 1… Weeding rate 5% or more and less than 20% 0… Weeding rate 5% or less (almost effective) None)

[Test Example 2] Test of herbicidal effect by weed growing season treatment under flooded conditions After putting alluvial soil in a Wagner pot of 1/10000 ares, water was added and mixed to obtain a flooded condition with a water depth of 4 cm. Seeds of Tainubier, Inuhotarui and Pontederia vaginalis were mixedly sown in the above cups and placed in a greenhouse at 25 to 30 ° C. to grow plants. When Tainubier, Inuhotarui and Pontederia vaginalis reached the 1st or 2nd leaf stage, the emulsion of the compound of the present invention prepared according to Formulation Example 2 was diluted with water to a predetermined dosage and treated on the surface of the water. Three weeks after the drug treatment, the effects on various plants were investigated according to the criteria of Test Example 1. The results are shown in Table 6.

[Test Example 3] Test of herbicidal effect by foliage treatment After putting alluvial soil in a Wagner pot of 1/10000 ares, water was added and mixed to make the condition of water depth 0.1 to 0.5 cm. Seeds of barnyard grass, leptochloa zebra, Cyperus iria and rice 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 so as to have a predetermined dosage, and the foliage was uniformly treated with a small spray. Three weeks after the drug treatment, the effects on various plants were investigated according to the criteria of Test Example 1. The results are shown in Table 7.

[Test Example 4] Test of herbicidal effect by foliage treatment Put sterilized burial soil in a plastic box with a length of 21 cm, a width of 13 cm, and a depth of 7 cm. , Corn, soybean, rice, wheat, beet and rapeseed seeds were sown in spots, covered with soil of about 1.5 cm, and then the plants were grown in a greenhouse at 25 to 30 ° C. After growing for 14 days, 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 the foliage was uniformly treated with a small spray. Three weeks after the drug treatment, the effects on various plants were investigated according to the criteria of Test Example 1. The results are shown in Table 8.

The symbols in Tables 5 to 8 have the following meanings.
A: Tainubier, B: Inuhotarui, C: Konagi, D: Azegaya, E: Kogomegayatsuri, F: Digitaria ciliaris, G: Setaria viridis, H: Inubier, M: Ichibi, N: Amaranthus retroflexus, O: White goosefoot, P: Hakobe, Q: Yaemgra, R: Amaranthus retroflexus, a: Transplanted rice, b: Directly sown rice, c: Corn, d: Soybean, e: Wheat, f: Beet, g: Rapeseed In addition, the treatment dose (g / ha) is 1 hectare ( It indicates that the concentration was adjusted so that the number of grams (g) of the stated numerical value was processed when converted per 1 ha).
In the table, "1-1-882 / 1-2-882" is the result of a test conducted using the compound synthesized by the method described in Synthesis Example 5.

[Table 5]
―――――――――――――――――――――――――――――
No. Processing dose ABC a
(g / ha)
―――――――――――――――――――――――――――――
1-1-304 1280 5 4 5 1
1-2-221 320 3 0 0 0
―――――――――――――――――――――――――――――

[Table 6]
―――――――――――――――――――――――――――――
No. Processing dose ABC
(g / ha)
―――――――――――――――――――――――――――――
1-1-304 1280 4 4 4
―――――――――――――――――――――――――――――

[Table 7]
―――――――――――――――――――――――――――――
No. Treatment dose HDE b
(g / ha)
―――――――――――――――――――――――――――――
1-1-304 320 5 5 5 0
1-1-524 320 5 5 4 0
1-1-744 320 4 5 4 0
1-1-881 320 2 2 0 0
1-1-882 / 1-2882 320 0 2 1 0
1-2-231 320 4 0 0 0
1-2-242 320 4 0 0 0
1-2-274 320 4 0 0 0
1-2-282 320 4 0 0 0
―――――――――――――――――――――――――――――

[Table 8]
――――――――――――――――――――――――――――――――――
No. Treatment dose FGHMNOPQR bcdefg
(g / ha)
――――――――――――――――――――――――――――――――――
1-1-304 320 5 4 5 4 4 5 5 5 0 2 3 2 5 5
1-1-524 320 4 0 4 4 3 5 3 3 0 0 3 0 5 3
1-1-744 320 4 3 4 4 4 5 5 5 0 2 4 1 5 3
1-1-881 320 0 0 0 0 4 5 3 3 3 0 0 0 0 4 0
1-1-882 / 1-2882 320 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0
1-2-221 320 0 0 0 0 3 4 0 0 0 0 3 0 0 0
1-2-231 320 2 2 3 2 3 4 2 3 1 0 2 0 3 3
1-2-242 320 3 0 4 4 3 4 2 0 2 0 3 1 1 1
1-2-274 320 0 0 0 2 5 5 0 0 0 0 2 0 1 2
1-2-282 320 4 0 3 0 3 0 0 0 0 1 0 1 2
1-2-881 320 0 0 0 0 3 0 0 0 0 0 0 0 0 0
――――――――――――――――――――――――――――――――――

The heterocyclic 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 (9)

Equation (1):

[In the formula, Q represents a ring represented by any of Q-1, Q-2 or Q-3.

R ¹ is hydrogen atom, halogen _atom, C 1 -C ₆ ^alkyl, substituted in ^{R 1a} _(C 1 ~C _{6) alkyl,} C 1 -C _{6 alkylthio,} C 1 -C _{6 alkylsulfinyl, C} 1 ~ Represents C ₆ alkyl sulfonyl, C _{3 to} C ₆ cycloalkyl or (C _{1 to} C ₆ ) cycloalkyl substituted with R ^1b .
R ^1a represents a halogen atom, cyano, C _{3 to} C ₆ cycloalkyl, C _{1 to} C ₆ alkylthio, C _{1 to} C ₆ alkyl sulfinyl or C _{1 to} C ₆ alkyl sulfonyl.
R ^1b represents a halogen atom and represents
R ² represents a hydrogen atom, a halogen atom, a C _{1 to} C ₆ alkyl or a halo (C _{1 to} C ₆ ) alkyl.
R ³ is C _{1 to} C ₆ alkyl, C _{3 to} C ₆ cycloalkyl, C _{3 to} C ₆ cycloalkyl (C _{1 to} C ₆ ) alkyl, halo (C _{1 to} C ₆ ) alkyl, C _{2 to} C ₆ Alkenyl, halo (C _{2 to} C ₆ ) alkenyl, C _{2 to} C ₆ alkynyl, halo (C _{2 to} C ₆ ) alkynyl, (C _{1 to} C ₆ ) alkyl substituted with R ^3a , -C (O) R ¹⁰ , -C (O) OR ¹¹ , -C (O) SR ¹² , -C (O) N (R ¹³ ) R ¹⁴ , -C (S) OR ¹⁶ , -C (S) SR ¹⁷ , -S ( _O) 2 ^{R 18,} pyridin-2-yl, represents a 5-chloropyridin-2-yl or 5-trifluoromethyl-2-yl,
R ^3a is -OR ²¹ , -OC (O) R ²² , -OC (O) OR ²³ , -S (O) nR ²⁴ , -C (O) R ²⁵ , -C (O) OR ²⁶ , -C. Represents (O) SR ²⁷ , -C (O) N (R ²⁸ ) R ²⁹ , -N (R ³⁰ ) R ³¹ , cyano, nitro, naphthyl or G1.
R ⁴ represents a hydrogen atom or C _{1 to} C ₆ alkyl.
R ¹⁰ is C _{1 to} C ₆ alkyl, C _{3 to} C ₆ cycloalkyl, C _{3 to} C ₆ cycloalkyl (C _{1 to} C ₆ ) alkyl, halo (C _{1 to} C ₆ ) alkyl, C _{2 to} C _{6 alkenyl,} C 2 -C ₆ ^alkynyl, substituted in ^{R 10a} _(C 1 ~C ₆₎ alkyl or G1,
R ^10a contains C _{1 to} C ₆ alkoxy, C _{1 to} C ₆ alkylthio, C _{1 to} C ₆ alkyl sulfinyl, C _{1 to} C ₆ alkyl sulfonyl, C _{1 to} C ₆ alkyl carbonyl, phenoxy, cyano, nitro or G1. Represent,
R ¹¹ is C _{1 to} C ₆ alkyl, C _{3 to} C ₆ cycloalkyl, C _{3 to} C ₆ cycloalkyl (C _{1 to} C ₆ ) alkyl, halo (C _{1 to} C ₆ ) alkyl, C _{2 to} C _{6 alkenyl,} C 2 -C ₆ ^alkynyl, substituted in ^{R 11a} _(C 1 ~C ₆₎ alkyl or G1,
R ^11a represents C _{1 to} C ₆ alkoxy, tetrahydrofuran-2-yl or G1.
R ¹² represents C _{1 to} C ₆ alkyl or (C _{1 to} C ₆ ) alkyl substituted with R ^12a .
R ^12a represents C _{1 to} C ₆ alkoxycarbonyl or G1.
R ¹³ and R ¹⁴ are independently hydrogen atoms, C _{1 to} C ₆ alkyl, halo (C _{1 to} C ₆ ) alkyl, C _{1 to} C ₆ alkoxy (C _{1 to} C ₆ ) alkyl, and C _{2 to} C, respectively. _{6 alkenyl,} or represents C 2 -C ₆ alkynyl or phenyl, ^{or by R 13} to form a _C 2 -C ₆ alkylene chain together with ^{R 14,} the nitrogen atom ^{to which R 13} and ^{R 14} are bonded At this time, the alkylene chain may contain one O, S, S (O), S (O) ₂ or N (R ¹⁵ ).
R ¹⁵ represents C _{1 to} C ₆ alkyl and represents
R ¹⁶ and R ¹⁷ represent phenyl
R ¹⁸ represents C _{1 to} C ₆ alkyl, halo (C _{1 to} C ₆ ) alkyl, -N (R ¹⁹ ) R ²⁰ , R ^18a substituted (C _{1 to} C ₆ ) alkyl or G1.
R ^18a represents C _{1 to} C ₆ alkoxy or G1.
R ¹⁹ and R ²⁰ independently represent C _{1 to} C ₆ alkyl or phenyl, respectively.
R ²¹ , R ²² , R ²⁴ and R ²⁵ are independently C _{1 to} C ₆ alkyl, halo (C _{1 to} C ₆ ) alkyl, C _{1 to} C ₆ alkoxy (C _{1 to} C ₆ ) alkyl or G1 respectively. Represents
R ²³ represents C _{1 to} C ₆ alkyl or C _{3 to} C ₆ cycloalkyl.
R ²⁶ , R ²⁷ , R ²⁸ , R ²⁹ , R ³⁰ , R ³¹ , R ³³ , R ³⁴ , R ³⁵ , R ³⁶ , R ³⁷ and R ³⁸ each independently represent C _{1 to} C ₆ alkyl.
R ³² represents C _{1 to} C ₆ alkyl, halo (C _{1 to} C ₆ ) alkyl, C _{1 to} C ₆ alkyl carbonyl, C _{1 to} C ₆ alkoxycarbonyl or C _{1 to} C ₆ alkyl sulfonyl.
G1 represents a ring represented by any of G1-1 to G1-31.

Z ₁ is a halogen atom, C _{1 to} C ₆ alkyl, halo (C _{1 to} C ₆ ) alkyl, C _{2 to} C ₆ alkenyl, halo (C _{2 to} C ₆ ) alkenyl, C _{2 to} C ₆ alkynyl, halo ( C _{2 to} C ₆ ) alkynyl, C _{1 to} C ₆ alkoxy, halo (C _{1 to} C ₆ ) alkoxy, C _{1 to} C ₆ alkylthio, halo (C _{1 to} C ₆ ) alkyl thio, C _{1 to} C ₆ alkyl sulfinyl, Halo (C _{1 to} C ₆ ) alkyl sulfinyl, C _{1 to} C ₆ alkyl sulfonyl, halo (C _{1 to} C ₆ ) alkyl sulfonyl, C _{1 to} C ₆ alkoxy (C _{1 to} C ₆ ) alkyl, halo (C ₁ to C ₆ ) C ₆ ) Alkoxy (C _{1 to} C ₆ ) alkyl, C _{1 to} C ₆ alkyl thio (C _{1 to} C ₆ ) alkyl, halo (C _{1 to} C ₆ ) alkyl thio (C _{1 to} C ₆ ) alkyl, C _{1 to} C ₆ Alkyl sulfinyl (C _{1 to} C ₆ ) alkyl, halo (C _{1 to} C ₆ ) alkyl sulfinyl (C _{1 to} C ₆ ) alkyl, C _{1 to} C ₆ alkyl sulfonyl (C _{1 to} C ₆ ) alkyl, halo (C) _{1 to} C ₆ ) Alkylsulfonyl (C _{1 to} C ₆ ) Alkyl, C _{1 to} C ₆ alkoxy (C _{1 to} C ₆₎
) Alkoxy, cyano (C _{1 to} C ₆ ) alkyl, C _{1 to} C ₆ alkyl carbonyl, C _{1 to} C ₆ alkoxy carbonyl, -CHO, -NHR ³² , -N (R ³³ ) R ³⁴ , -C (O) Represents OH, -C (O) NH ₂ , -C (O) N (R ³⁵ ) R ³⁶ , -S (O) ₂ N (R ³⁷ ) R ³⁸ , hydroxy, -NH ₂ , cyano or nitro, p2 , when p3, p4 or the p5 represents an integer of 2 or more, each Z ₁ may be the even or different from each other the same as each other, further, when two of Z ₁ are adjacent, two adjacent _{Z 1} is -CH = CH-CH = CH - , - NH-CH = CH -, - S-CH = CH -, - O-CH = CH- or forming a -OCH ₂ O- Therefore, a 5-membered ring or a 6-membered ring may be formed together with the carbon atom to which each Z ₁ is bonded.
T ₁ represents a hydrogen atom, C _{1 to} C ₆ alkyl or halo (C _{1 to} C ₆ ) alkyl.
p1 represents an integer of 0 or 1,
p2 represents an integer of 0, 1 or 2,
p3 represents an integer of 0, 1, 2 or 3
p4 represents an integer of 0, 1, 2, 3 or 4
p5 represents an integer of 0, 1, 2, 3, 4 or 5
n represents an integer of 0, 1 or 2. ] Represented by a heterocyclic compound or a salt thereof. R ¹ is C _{1 to} C ₆ alkyl, R ¹ a substituted (C _{1 to} C ₆ ) alkyl, C _{1 to} C ₆ alkyl thio, C _{1 to} C ₆ alkyl sulfinyl, C _{1 to} C ₆ alkyl sulfonyl or R. ^Represents a (C _1- C ₆ ) cycloalkyl substituted with ^1b .
R ^1a represents C _{1 to} C ₆ alkylthio, C _{1 to} C ₆ alkyl sulfinyl or C _{1 to} C ₆ alkyl sulfonyl.
R ² represents halo (C _{1 to} C ₆ ) alkyl and represents
R ³ was replaced with C _{1 to} C ₆ alkyl, C _{3 to} C ₆ cycloalkyl (C _{1 to} C ₆ ) alkyl, C _{2 to} C ₆ alkenyl, C _{2 to} C ₆ alkynyl, and R ^3a (C _1). ~ C ₆ ) Alkyne, -C (O) R ¹⁰ , -C (O) OR ¹¹ , -C (O) N (R ¹³ ) R ¹⁴ or -S (O) ₂ R ¹⁸
R ^3a represents -OR ²¹ , -OC (O) OR ²³ , cyano or G1.
R ¹⁰ represents C _{1 to} C ₆ alkyl or G1
R ¹¹ represents C _{1 to} C ₆ alkyl and represents
R ¹³ and R ¹⁴ each independently represent C _{1 to} C ₆ alkyl, or R ¹³ can be combined with R ¹⁴ to form a C _{2 to} C ₆ alkylene chain, thereby forming R ¹³ and R. ^{It represents that 14} forms a 3- to 7-membered ring with the nitrogen atom to which it binds, even if the alkylene chain contains one O, S, S (O), S (O) ₂ or N (R ¹⁵ ) Often,
R ¹⁸ represents C _{1 to} C ₆ alkyl, -N (R ¹⁹ ) R ²⁰ or G1.
R ¹⁹ and R ²⁰ independently represent C _{1 to} C ₆ alkyl, respectively.
R ²¹ is the heterocyclic compound according to claim 1 or a salt thereof, which represents C _{1 to} C ₆ alkyl. The heterocyclic compound according to claim 2 or a salt thereof, wherein Q represents a ring represented by Q-1. The heterocyclic compound according to claim 2 or a salt thereof, wherein Q represents a ring represented by Q-2. The heterocyclic compound according to claim 2 or a salt thereof, wherein Q represents a ring represented by Q-3. R ³ is C _{1 to} C ₆ alkyl, C _{3 to} C ₆ cycloalkyl (C _{1 to} C ₆ ) alkyl, C _{2 to} C ₆ alkenyl, (C _{1 to} C ₆ ) alkyl substituted with R ^3a or- Represents C (O) OR ¹¹
R ^3a represents -OR ²¹ , -OC (O) OR ²³ or G1.
R ²³ represents C _{1 to} C ₆ alkyl and represents
G1 represents G1-1 or G1-3
Z ₁ represents a halogen atom
p4 represents an integer of 1 and represents
The heterocyclic compound according to claim 3 or a salt thereof, wherein p5 represents an integer of 0. R ³ is C _{1 to} C ₆ alkyl, C _{3 to} C ₆ cycloalkyl (C _{1 to} C ₆ ) alkyl, C _{2 to} C ₆ alkenyl, (C _{1 to} C ₆ ) alkyl substituted with R ^3a or- Represents C (O) OR ¹¹
R ^3a represents -OR ²¹ , -OC (O) OR ²³ or G1.
R ²³ represents C _{1 to} C ₆ alkyl and represents
G1 represents G1-1 or G1-3
Z ₁ represents a halogen atom
p4 represents an integer of 1 and represents
The heterocyclic compound according to claim 4 or a salt thereof, wherein p5 represents an integer of 0. A pesticide containing one or more selected from the heterocyclic amide compound according to claim 1 to claim 7 and a salt thereof as an active ingredient. A herbicide containing one or more selected from the heterocyclic amide compound according to claims 1 to 7 and a salt thereof as an active ingredient.