JP2018177729A - Nitrogen-containing condensed heterocyclic carboxamide compound and herbicide containing the compound and method of using the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a novel herbicide having both of high safety for crops and excellent herbicidal activity for weeds.SOLUTION: A herbicide contains a nitrogen-containing condensed heterocyclic carboxamide compound represented by formula (1), or a salt thereof as an active ingredient. [Rand Rindependently represent H, halogen, halogen-substituted/unsubstituted alkyl, halogen-substituted/unsubstituted alkenyl, halogen-substituted/unsubstituted alkoxy or the like; Ris H, alkyl, alcarbonyl, alkoxycarbonyl or the like; ring A is A1-A4; H, alkyl; Ris H or halogen-substituted/unsubstituted alkyl; r1 is an integer of 1-3; r2 is an integer of 1-4].SELECTED DRAWING: None

Description

The present invention relates to a herbicide containing a nitrogen-containing fused heterocyclic carboxamide compound or a salt thereof as an active ingredient and a method of using the same.

Patent documents 1, 3, 6 and 7 disclose that certain pyrrolidinone-3-carboxamide derivatives have herbicidal activity. Patent Document 2 also describes that certain piperidinone-3-carboxamide compounds have herbicidal activity. In addition, Patent Document 4 describes that certain butyrolactone-3-carboxamide compounds have herbicidal activity. In addition, Patent Document 5 describes that certain fused heterocyclic carboxamide compounds have herbicidal activity. However, such a document does not disclose a compound having a fused ring structure in which a substituent on the 1-position nitrogen atom of pyrrolidinone and a substituent on the 5-position are bonded.

International Publication No. 2015/084796 Brochure WO 2016/003997 pamphlet International Publication No. 2016/164201 brochure International Publication No. 2016/176082 brochure International Publication No. 2016/182780 Brochure International Publication No. 2016/196019 Pamphlet International Publication No. 2016/196593 brochure

  A stable supply of food is essential for the alleviation of the food crisis that accompanies the expected global population growth in the near future. Stable food supply requires economic and efficient killing or control of weeds that become obstacles during cultivation and harvesting, and development of new herbicides and plant growth regulators that can be the solution It is becoming more important. An object of the present invention is to provide a novel herbicide having both high safety for crops and excellent herbicidal activity for weeds in order to meet such social needs. In addition, with the aging of farmers, various labor-saving application methods are required, and the creation of herbicides having characteristics suitable for these application methods is also required.

  As a result of intensive studies to develop novel herbicides, the present inventors have found that the compound represented by the general formula (1) of the present invention or a salt thereof is useful as a herbicide, and the present invention Completed.

That is, the present invention
[1] General formula (1)
{Wherein R ¹ and R ³ are each independently
(a1) hydrogen atom;
(a2) halogen atom;
(a3) cyano group;
(a4) nitro group;
(a5) (C ₁ -C ₆ ) alkyl group;
(a6) (C ₂ -C ₆ ) alkenyl group;
(a7) (C ₂ -C ₆ ) alkynyl group;
(a8) (C ₃ -C ₆ ) cycloalkyl group;
(a9) (C ₁ -C ₆ ) alkoxy group;
(a10) halo (C ₁ -C ₆ ) alkyl group;
(a11) halo (C ₂ -C ₆ ) alkenyl group;
(a12) halo (C ₂ -C ₆ ) alkynyl group;
(a13) halo (C ₃ -C ₈ ) cycloalkyl group;
(a14) halo (C ₁ -C ₆ ) alkoxy group
(a15) (C ₁ -C ₆ ) alkylthio group;
(a16) (C ₁ -C ₆ ) alkylsulfinyl group;
(a17) (C ₁ -C ₆ ) alkylsulfonyl group;
(a18) halo (C ₁ -C ₆ ) alkylthio group;
(a19) halo (C ₁ -C ₆ ) alkylsulfinyl group;
(a20) halo (C ₁ -C ₆ ) alkylsulfonyl group;
(a21) phenyl group;
(a22) phenyloxy group; or
(a23) Phenyl (C ₁ -C ₆ ) alkyl group is shown.
p and q each independently represent an integer of 1 to 5;
R ² is
(b1) hydrogen atom;
(b2) (C ₁ -C ₆ ) alkyl group;
(b3) (C ₁ -C ₆ ) alkylcarbonyl group;
(b4) (C ₁ -C ₆ ) alkoxycarbonyl group; or
(b5) R ⁸ R ⁹ N carbonyl group (wherein R ⁸ and R ⁹ are each independently a hydrogen atom; (C ₁ -C ₆ ) alkyl group; halo (C ₁ -C ₆ ) alkyl group; phenyl group Or a phenyl (C ₁ -C ₆ ) alkyl group is shown).
Ring A represents the following structure A1; A2; A3 or A4.
(In the formula, ● indicates a bonding position,
Each R ⁴ is independently
(d1) hydrogen atom;
(d2) (C ₁ -C ₆ ) alkyl group; or
(d3) represents a halo (C ₁ -C ₆ ) alkyl group,
r1 represents an integer of 1 to 3;
r2 represents an integer of 1 to 4; )}
A compound represented by or a salt thereof
[2] R ¹ and R ³ are each independently
(a1) hydrogen atom;
(a2) halogen atom;
(a5) (C ₁ -C ₆ ) alkyl group; or
(a10) halo (C ₁ -C ₆ ) alkyl group,
R ² is
(b1) hydrogen atom,
Ring A is A1
R ⁴ is
(d1) The compound according to the above [1], which is a hydrogen atom, or a salt thereof,
[3] R ¹ is
(a2) a halogen atom,
R ³ is
(a1) hydrogen atom; or
(a10) The compound or the salt thereof according to the above [1] or [2], which is a halo (C ₁ -C ₆ ) alkyl group.
[4] A herbicide comprising the compound according to any one of the above [1] to [3] or a salt thereof as an active ingredient,
[5] A method of using a herbicide, which comprises treating plants or soil with an effective amount of the herbicide according to [4].
[6] The present invention relates to the use of the compound according to any one of the above [1] to [3] or a salt thereof as a herbicide.

  The compounds of the present invention or salts thereof have excellent effects as herbicides.

In the definition of the general formula (1) of the compounds according to the invention,
"Halo" means "halogen atom" and represents a chlorine atom, a bromine atom, an iodine atom or a fluorine atom.

The “(C ₁ -C ₆ ) alkyl group” is, for example, methyl group, ethyl group, normal propyl group, isopropyl group, normal butyl group, isobutyl group, secondary butyl group, tertiary butyl group, normal pentyl group, isopentyl group , Tertiary pentyl group, neopentyl group, 2,3-dimethylpropyl group, 1-ethylpropyl group, 1-methylbutyl group, 2-methylbutyl group, normal hexyl group, isohexyl group, 2-hexyl group, 3-hexyl group, Indicates a linear or branched alkyl group having 1 to 6 carbon atoms, such as 2-methylpentyl group, 3-methylpentyl group, 1,1,2-trimethylpropyl group, 3,3-dimethylbutyl group, etc. .

The "(C ₂ -C ₆ ) alkenyl group" is, for example, a vinyl group, an allyl group, an isopropenyl group, a 1-butenyl group, a 2-butenyl group, a 2-methyl-2-propenyl group, a 1-methyl-2- group. A linear or branched alkenyl group having 2 to 6 carbon atoms, such as propenyl group, 2-methyl-1-propenyl group, pentenyl group, 1-hexenyl group, 3,3-dimethyl-1-butenyl group And “(C ₂ -C ₆ ) alkynyl group” means, for example, ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 3-methyl-1 -Linear or branched carbon such as -propynyl group, 2-methyl-3-propynyl group, pentynyl group, 1-hexynyl group, 3-methyl-1-butynyl group, 3,3-dimethyl-1-butynyl group 2 to 6 atoms Indicating the group.

The “(C ₃ -C ₆ ) cycloalkyl group” is a cyclic alkyl group having 3 to 6 carbon atoms, such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group and the like, and “(C ₁ − As C ₆ ) alkoxy group ”, for example, methoxy group, ethoxy group, normal propoxy group, isopropoxy group, normal butoxy group, secondary butoxy group, tertiary butoxy group, normal pentyloxy group, isopentyloxy group, tertiary Pentyloxy group, neopentyloxy group, 2,3-dimethylpropyloxy group, 1-ethylpropyloxy group, 1-methylbutyloxy group, normal hexyloxy group, isohexyloxy group, 1,1,2-trimethylpropyl group Linear or branched C 1 to C 6 carbon atoms such as oxy group It shows the Kokishi group.

Examples of “(C ₁ -C ₆ ) alkylthio group” include methylthio group, ethylthio group, normal propylthio group, isopropylthio group, normal butylthio group, secondary butylthio group, tertiary butylthio group, normal pentylthio group. Group, isopentylthio group, tertiary pentylthio group, neopentylthio group, 2,3-dimethylpropylthio group, 1-ethylpropylthio group, 1-methylbutylthio group, normal hexylthio group, isohexylthio group And a linear or branched alkylthio group having 1 to 6 carbon atoms such as 1,1,2-trimethylpropylthio group.

Examples of “(C ₁ -C ₆ ) alkylsulfinyl group” include methylsulfinyl group, ethylsulfinyl group, normal propylsulfinyl group, isopropylsulfinyl group, normal butylsulfinyl group, secondary butylsulfinyl group, tertiary butylsulfinyl group, Normal pentyl sulfinyl group, isopentyl sulfinyl group, tertiary pentyl sulfinyl group, neopentyl sulfinyl group, 2,3-dimethylpropyl sulfinyl group, 1-ethylpropylsulfinyl group, 1-methylbutylsulfinyl group, normal hexylsulfinyl group, iso Indicates a linear or branched C1-C6 alkylsulfinyl group such as hexylsulfinyl group or 1,1,2-trimethylpropylsulfinyl group .

Examples of the “(C ₁ -C ₆ ) alkylsulfonyl group” include a methylsulfonyl group, an ethylsulfonyl group, a normal propylsulfonyl group, an isopropylsulfonyl group, a normal butylsulfonyl group, a secondary butylsulfonyl group, and a tertiary butylsulfonyl group, Normal pentyl sulfonyl group, isopentyl sulfonyl group, tertiary pentyl sulfonyl group, neopentyl sulfonyl group, 2,3-dimethylpropyl sulfonyl group, 1-ethylpropyl sulfonyl group, 1-methyl butyl sulfonyl group, normal hexyl sulfonyl group, iso It represents a linear or branched C1-C6 alkylsulfonyl group such as hexylsulfonyl group or 1,1,2-trimethylpropylsulfonyl group.

The “(C ₁ -C ₆ ) alkylcarbonyl group” is, for example, an acetyl group, a propanoyl group, a butanoyl group, a 2-methylpropanoyl group, a pentanoyl group, a 2-methylbutanoyl group, a 3-methylbutanoyl group, pivaloyl group, a hexanoyl group, an alkylcarbonyl group having a (C 1 _{-C 6)} alkyl group such as a cyclopropylcarbonyl group, i.e., an alkylcarbonyl group having 2 to 7 carbon atoms.

The “(C ₁ -C ₆ ) alkoxycarbonyl group” is, for example, a methoxycarbonyl group, an ethoxycarbonyl group, a normal propoxycarbonyl group, an isopropoxycarbonyl group, a normal butoxycarbonyl group, an isobutoxycarbonyl group, a secondary butoxycarbonyl group, tert-butoxycarbonyl group, an alkoxycarbonyl group having an (C 1 _{-C 6)} alkoxy group such as pentyloxycarbonyl group, that is, the alkoxycarbonyl group having 2 to 7 carbon atoms.

The above “(C ₁ -C ₆ ) alkyl group”, “(C ₂ -C ₆ ) alkenyl group”, “(C ₂ -C ₆ ) alkynyl group”, “(C ₃ -C ₆ ) cycloalkyl group”, "(C ₁ -C ₆ ) alkoxy group", "(C ₁ -C ₆ ) alkylthio group", "(C ₁ -C ₆ ) alkylsulfinyl group" or "(C ₁ -C ₆ ) alkylsulfonyl group", etc. One or more halogen atoms may be substituted at the substitutable position of, and when two or more halogen atoms are substituted, the halogen atoms may be the same or different. “Halo (C ₁ -C ₆ ) alkyl group”, “halo (C ₂ -C ₆ ) alkenyl group”, “halo (C ₂ -C ₆ ) alkynyl group”, “halo (C ₃ -C ₆ )” respectively "Cycloalkyl", "halo (C ₁ -C ₆ ) alkoxy", "halo (C ₁ -C ₆ ) alkylthio", "halo (C ₁ -C ₆ ) alkylsulfinyl" or "halo (C ₁₎ —C ₆ ) alkylsulfonyl group ”.

The expressions “(C ₁ -C ₆ )”, “(C ₂ -C ₆ )”, “(C ₃ -C ₆ )” and the like indicate the range of carbon atoms in various substituents. Further, it is possible to show the definition of groups in which the substituent is linked, for example, "(C 1 _{-C 6)} alkoxy (C 1 _{-C 6)} alkyl group" for straight-chain or branched It shows that a C1-C6 alkoxy group is bonded to a linear or branched C1-C6 alkyl group.

  Examples of salts of the compound represented by the general formula (1) of the present invention include mineral acid salts such as hydrochloride, sulfate, nitrate, and phosphate, acetate, fumarate, maleate, oxalate, Examples thereof include organic acid salts such as methanesulfonic acid salt, benzenesulfonic acid salt and para-toluenesulfonic acid salt, and salts with an inorganic or organic base such as sodium ion, potassium ion, calcium ion and trimethyl ammonium.

  The compound represented by the general formula (1) of the present invention and salts thereof may have one or more asymmetric centers in the structural formula, and two or more optical isomers and diastereomers When present, the present invention includes all of the respective optical isomers and the mixture in which they are contained in any proportion. In the compounds represented by the general formula (1) of the present invention and salts thereof, two geometric isomers derived from carbon-carbon double bonds may be present in the structural formula. These include all geometric isomers of each and mixtures in which they are contained in arbitrary proportions.

Preferred embodiments of the compound represented by the general formula (1) of the present invention are shown below.
Preferably R ¹ is
(a1) hydrogen atom;
(a2) halogen atom;
(a5) (C ₁ -C ₆ ) alkyl group; or
(a10) halo (C ₁ -C ₆ ) alkyl group,
More preferably,
(a2) It is a halogen atom.
Preferably R ² is
(b1) It is a hydrogen atom.
Preferably R ³ is
(a1) hydrogen atom;
(a2) halogen atom;
(a5) (C ₁ -C ₆ ) alkyl group; or
(a10) halo (C ₁ -C ₆ ) alkyl group,
More preferably,
(a1) hydrogen atom; or
(a10) A halo (C ₁ -C ₆ ) alkyl group.
Preferred as ring A is A1.
Preferably R ⁴ is
(d1) It is a hydrogen atom.

  The various compounds of the present invention can be produced, for example, by the following production methods, but the present invention is not limited thereto.

Manufacturing method 1
In the formula, R ¹ , R ² , R ³ , R ⁴ , p, q and r 1 are as defined above, and R represents a (C ₁ -C ₃ ) alkyl group.

The compounds represented by General Formula (1-1) of the present invention can be produced by the following steps [a] to [f].
Process [a] The process of manufacturing the compound represented by General formula (8) by condensing the compound represented by General formula (10), and the compound represented by General formula (9).
Process [b] The process of manufacturing the compound represented by General formula (6) by making the compound represented by General formula (8), and the compound represented by General formula (7) react.
Step [c] A step of producing a compound represented by General Formula (5) by performing an intramolecular cyclization reaction from the compound represented by General Formula (6).
Process [d] The process of manufacturing the compound represented by General formula (4) by performing a reductive reaction from the compound represented by General formula (5).
Process [e] The process of manufacturing the compound represented by General formula (3) by hydrolyzing an ester group from the compound represented by General formula (4).
Step [f] The compound represented by General Formula (1-1) is produced by performing an amidation reaction from the compound represented by General Formula (3) and the compound represented by General Formula (2) Process.

Production Method of Step [a] The compound represented by the general formula (8) comprises a compound represented by the general formula (10) and a compound represented by the general formula (9) in the presence of a base and an inert solvent. It can be produced by condensation.

As a base that can be used in this reaction, for example, inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogencarbonate, potassium hydrogencarbonate, sodium hydride, potassium hydride and the like Alkali metal hydrides, alkali metal alkoxides such as potassium t-butoxide, sodium methoxide, sodium ethoxide, etc., triethylamine, diisopropylethylamine, third substances such as 1,8-diazabicyclo [5.4.0] undec-7-ene and the like Secondary amines, pyridine, nitrogen-containing aromatic compounds such as dimethylaminopyridine, etc. can be exemplified, and the amount thereof used is usually 0.1 times mol to 10 times the amount of the compound represented by the general formula (10) It may be appropriately selected from the range of moles.

The inert solvent used in this reaction may be any solvent which does not significantly inhibit the progress of this reaction, and examples thereof include aromatic hydrocarbons such as benzene, toluene and xylene, methylene chloride, chloroform and carbon tetrachloride Halogenated hydrocarbons, halogenated aromatic hydrocarbons such as chlorobenzene, dichlorobenzene, etc., linear or cyclic ethers such as diethyl ether, methyl tertiary butyl ether, dioxane, tetrahydrofuran, etc. esters such as ethyl acetate, dimethylformamide, Examples include inert solvents such as amides such as dimethylacetamide, ketones such as acetone and methyl ethyl ketone, aprotic polar solvents such as dimethyl sulfoxide, 1,3-dimethyl-2-imidazolidinone and the like. Inert solvents may be used alone or in combination of two or more It is possible to use Te. The amount thereof to be used may be appropriately selected usually from the range of 0.1 to 100 L with respect to 1 mol of the compound represented by the general formula (10).

Since this reaction is an equimolar reaction, equimolar amounts of each reactant may be used, but any reactant may be used in excess. The reaction temperature can be usually from room temperature to the boiling point range of the inert solvent used, and the reaction time is not constant depending on the reaction scale and reaction temperature, but may be usually from several minutes to 48 hours. After completion of the reaction, the desired product may be isolated from the reaction system containing the desired product by a conventional method, and the desired product can be produced by purification by recrystallization, column chromatography, etc., as necessary.

Process for Producing Step [b] The compound represented by the general formula (6) is a compound represented by the general formula (8) in the presence of a catalyst and an inert solvent, and a compound represented by the general formula (7) Can be produced according to the method described in Tetrahedron, 2007, 63, 5608-5613.

Process for Producing Step [c] The compound represented by the general formula (5) can be produced by reacting the compound represented by the general formula (6) in the presence of a base and an inert solvent.

As a base that can be used in this reaction, for example, inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogencarbonate, potassium hydrogencarbonate, sodium hydride, potassium hydride and the like Alkali metal hydrides, alkali metal alkoxides such as potassium t-butoxide, sodium methoxide, sodium ethoxide, etc., triethylamine, diisopropylethylamine, third substances such as 1,8-diazabicyclo [5.4.0] undec-7-ene and the like Secondary amines, pyridine, nitrogen-containing aromatic compounds such as dimethylaminopyridine, etc. can be exemplified, and the amount thereof used is usually 1-fold mol to 10-fold mol relative to the compound represented by General Formula (6) It may be suitably selected from the range of

The inert solvent used in this reaction may be any solvent which does not significantly inhibit the progress of this reaction, and examples thereof include aromatic hydrocarbons such as benzene, toluene and xylene, methylene chloride, chloroform and carbon tetrachloride Halogenated hydrocarbons, halogenated aromatic hydrocarbons such as chlorobenzene, dichlorobenzene, etc., linear or cyclic ethers such as diethyl ether, methyl tertiary butyl ether, dioxane, tetrahydrofuran, etc. esters such as ethyl acetate, dimethylformamide, Examples include inert solvents such as amides such as dimethylacetamide, ketones such as acetone and methyl ethyl ketone, aprotic polar solvents such as dimethyl sulfoxide, 1,3-dimethyl-2-imidazolidinone and the like. Inert solvents may be used alone or in combination of two or more It is possible to use Te. The amount thereof used may be appropriately selected usually from the range of 0.1 to 100 L with respect to 1 mol of the compound represented by the general formula (6).

The reaction temperature of this reaction can be usually from room temperature to the boiling point range of the inert solvent used, and the reaction time is not constant depending on the reaction scale and reaction temperature, but it may be usually from several minutes to 48 hours. After completion of the reaction, the desired product may be isolated from the reaction system containing the desired product by a conventional method, and the desired product can be produced by purification by recrystallization, column chromatography, etc., as necessary.

Process for Producing Step [d] The compound represented by the general formula (4) can be produced by reducing the compound represented by the general formula (5) in the presence of hydrogen gas, a catalyst and an inert solvent .

  As a catalyst which can be used by this reaction, Pd-C, Pt-C, Raney Ni, platinum oxide etc. can be illustrated, for example, As the amount of its use, it is to 1 mmol of compounds represented by General formula (5) In general, it may be properly selected from the range of 0.01 g to 5 g.

The inert solvent used in this reaction may be any solvent which does not significantly inhibit the progress of the reaction, for example, esters such as ethyl acetate, alcohol solvents such as methanol and ethanol, carboxylic acids such as acetic acid, water, etc. Inert solvents of the following can be exemplified, and these inert solvents can be used alone or in combination of two or more. The amount thereof to be used may be appropriately selected usually in the range of 0.1 to 100 L per 1 mol of the compound represented by the general formula (5).

The reaction temperature of this reaction can be usually from room temperature to the boiling point range of the inert solvent used, and the reaction time is not constant depending on the reaction scale and reaction temperature, but it may be usually from several minutes to 48 hours. After completion of the reaction, the desired product may be isolated from the reaction system containing the desired product by a conventional method, and the desired product can be produced by purification by recrystallization, column chromatography, etc., as necessary.

Manufacturing method of process [e] The compound represented by General formula (3) may be manufactured by hydrolyzing the compound represented by General formula (4) using the conventional method used by organic synthesis it can.

Process for Producing Step [f] The compound represented by the general formula (1) is represented by the compound represented by the general formula (3) in the presence of a condensing agent, a base and an inert solvent, and the compound represented by the general formula (2) It can be produced by reacting with a compound.

Examples of the condensing agent used in this reaction include 50% propylphosphonic anhydride in ethyl acetate, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (EDC), diethyl cyanophosphate (DEPC), Examples thereof include carbonyl diimidazole (CDI), 1,3-dicyclohexyl carbodiimide (DCC), chlorocarbonic esters, 2-chloro-1-methylpyridinium iodide and the like, and the amount thereof used is represented by the general formula (3) It may select suitably from the range of 1 time mole-3 times mole with respect to the compound represented by these, and should just use it.

Examples of the base include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogencarbonate and potassium hydrogencarbonate, acetates such as sodium acetate and potassium acetate, triethylamine, diisopropylethylamine, 1, Examples include tertiary amines such as 8-diazabicyclo [5.4.0] undec-7-ene, and nitrogen-containing aromatic compounds such as pyridine and dimethylaminopyridine. It may be suitably selected from the range of usually 1-fold mol to 10-fold mol with respect to the compound represented by (3).

The inert solvent used in this reaction may be any solvent which does not significantly inhibit the progress of this reaction, and examples thereof include aromatic hydrocarbons such as benzene, toluene and xylene, methylene chloride, chloroform and carbon tetrachloride Halogenated hydrocarbons, halogenated aromatic hydrocarbons such as chlorobenzene, dichlorobenzene, etc., linear or cyclic ethers such as diethyl ether, methyl tertiary butyl ether, dioxane, tetrahydrofuran, etc. esters such as ethyl acetate, dimethylformamide, Examples include inert solvents such as amides such as dimethylacetamide, ketones such as acetone and methyl ethyl ketone, aprotic polar solvents such as dimethyl sulfoxide, 1,3-dimethyl-2-imidazolidinone and the like. Inert solvents may be used alone or in combination of two or more It is possible to use Te. The amount thereof to be used may be appropriately selected usually from the range of 0.1 to 100 L with respect to 1 mole of the compound represented by the general formula (3).

Since this reaction is an equimolar reaction, equimolar amounts of each reactant may be used, but any reactant may be used in excess. The reaction temperature can be usually from room temperature to the boiling point range of the inert solvent used, and the reaction time is not constant depending on the reaction scale and reaction temperature, but may be usually from several minutes to 48 hours. After completion of the reaction, the desired product may be isolated from the reaction system containing the desired product by a conventional method, and the desired product can be produced by purification by recrystallization, column chromatography, etc., as necessary.

Manufacturing method 2
In the formula, R ¹ , R ² , R ³ , R ⁴ , R, p, q and r 2 are as defined above, and X represents a halogen atom.

The compound represented by the general formula (1-2) of the present invention can be prepared from the compound represented by the general formula (12), which can be produced by the following steps [g] and [h]: It can manufacture by process [e] and [f] of the said manufacturing method 1 through the compound represented by General formula (11) manufactured by [d].
Step [g] A step of producing a compound represented by General Formula (14) by condensing the compound represented by General Formula (15) and the compound represented by General Formula (9).
Step [h] A step of producing a compound represented by the general formula (12) by reacting the compound represented by the general formula (14) with the compound represented by the general formula (13).

Process for Producing Step [g] The compound represented by the general formula (14) comprises a compound represented by the general formula (15) and a compound represented by the general formula (9) in the presence of a base and an inert solvent. It can be produced by condensation.

As a base that can be used in this reaction, for example, inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogencarbonate, potassium hydrogencarbonate, sodium hydride, potassium hydride and the like Alkali metal hydrides, alkali metal alkoxides such as potassium t-butoxide, sodium methoxide, sodium ethoxide, etc., triethylamine, diisopropylethylamine, third substances such as 1,8-diazabicyclo [5.4.0] undec-7-ene and the like Secondary amines, pyridine, nitrogen-containing aromatic compounds such as dimethylaminopyridine, etc. can be exemplified, and the amount thereof used is usually 0.1 times mol to 10 times the amount of the compound represented by the general formula (15) It may be appropriately selected from the range of moles.

The inert solvent used in this reaction may be any solvent which does not significantly inhibit the progress of this reaction, and examples thereof include aromatic hydrocarbons such as benzene, toluene and xylene, methylene chloride, chloroform and carbon tetrachloride Halogenated hydrocarbons, halogenated aromatic hydrocarbons such as chlorobenzene, dichlorobenzene, etc., linear or cyclic ethers such as diethyl ether, methyl tertiary butyl ether, dioxane, tetrahydrofuran, etc. esters such as ethyl acetate, dimethylformamide, Examples include inert solvents such as amides such as dimethylacetamide, ketones such as acetone and methyl ethyl ketone, aprotic polar solvents such as dimethyl sulfoxide, 1,3-dimethyl-2-imidazolidinone and the like. Inert solvents may be used alone or in combination of two or more It is possible to use Te. The amount thereof to be used may be appropriately selected usually in the range of 0.1 to 100 L per 1 mol of the compound represented by the general formula (15).

Since this reaction is an equimolar reaction, equimolar amounts of each reactant may be used, but any reactant may be used in excess. The reaction temperature can be usually from room temperature to the boiling point range of the inert solvent used, and the reaction time is not constant depending on the reaction scale and reaction temperature, but may be usually from several minutes to 48 hours. After completion of the reaction, the desired product may be isolated from the reaction system containing the desired product by a conventional method, and the desired product can be produced by purification by recrystallization, column chromatography, etc., as necessary.

Process for Producing Step [h] The compound represented by the general formula (12) is obtained by reacting the compound represented by the general formula (14) with the compound represented by the general formula (13) in the presence of an inert solvent It can be manufactured by

As the inert solvent used in this reaction, any solvent which does not significantly inhibit the progress of this reaction may be used. For example, linear or cyclic saturated hydrocarbons such as pentane, hexane and cyclohexane, diethyl ether, methyl tertiary butyl ether Inert solvents such as linear or cyclic ethers such as dioxane and tetrahydrofuran can be exemplified, and these inert solvents can be used alone or in combination of two or more. The amount thereof to be used may be appropriately selected usually in the range of 0.1 to 100 L with respect to 1 mol of the compound represented by the general formula (14).

Since this reaction is an equimolar reaction, equimolar amounts of each reactant may be used, but any reactant may be used in excess. The reaction temperature can be usually from room temperature to the boiling point range of the inert solvent used, and the reaction time is not constant depending on the reaction scale and reaction temperature, but may be usually from several minutes to 48 hours. After completion of the reaction, the desired product may be isolated from the reaction system containing the desired product by a conventional method, and the desired product can be produced by purification by recrystallization, column chromatography, etc., as necessary.

Manufacturing method 3
In the formula, R ¹ , R ² , R ³ , R ⁴ , R, p, q and r 1 are as defined above.

  The compound represented by the general formula (1-3) of the present invention can be produced from the compound represented by the general formula (5) by the steps [e] and [f] of the production method 1.

Manufacturing method 4
In the formula, R ¹ , R ² , R ³ , R ⁴ , R, p, q and r 1 are as defined above.

The compound represented by the general formula (1-4) of the present invention can be produced from the compound represented by the general formula (16) which can be produced by the following step [i] And [f].
Step [i] A step of producing a compound represented by the general formula (16) by partially reducing the compound represented by the general formula (5).

Process for Producing Step [i] The compound represented by the general formula (16) is produced by partially reducing the compound represented by the general formula (5) in the presence of hydrogen gas, a catalyst and an inert solvent can do.

  As a catalyst which can be used by this reaction, Pd-C, Pt-C, Raney Ni, platinum oxide etc. can be illustrated, for example, As the amount of its use, it is to 1 mmol of compounds represented by General formula (5) In general, it may be properly selected from the range of 0.01 g to 5 g.

The inert solvent used in this reaction may be any solvent which does not significantly inhibit the progress of the reaction, for example, esters such as ethyl acetate, alcohol solvents such as methanol and ethanol, carboxylic acids such as acetic acid, water, etc. Inert solvents of the following can be exemplified, and these inert solvents can be used alone or in combination of two or more. The amount thereof to be used may be appropriately selected usually in the range of 0.1 to 100 L per 1 mol of the compound represented by the general formula (5).

The reaction temperature of this reaction can be usually from room temperature to the boiling point range of the inert solvent used, and the reaction time is not constant depending on the reaction scale and reaction temperature, but it may be usually from several minutes to 48 hours. After completion of the reaction, the desired product may be isolated from the reaction system containing the desired product by a conventional method, and the desired product can be produced by purification by recrystallization, column chromatography, etc., as necessary.

The representative examples of the compound represented by the general formula (1) of the present invention are illustrated in Tables 1 to 3 below, but the present invention is not limited thereto.
In the table, "Me" represents a methyl group. Physical properties indicate melting point (° C.) or refractive index n _D (measurement temperature).
Table 1 shows ¹ H-NMR data of the compounds described as “NMR” in the column of physical properties in Table ¹ .

Note) Compound numbers I-2 and I-3 are in a diastereomeric relationship with each other, and separate each diastereomer at the precursor stage. The derivative derived from the precursor having a small Rf value is I-2, and the derivative derived from a precursor having a large Rf value is I-3.

  The useful plant to which the compound represented by the general formula (1) of the present invention or a salt thereof can be used is not particularly limited, but, for example, cereals (eg, rice, barley, wheat, rye, oats, Corn, etc.), Beans (soybean, red beans, broad beans, peas, beans, peanuts, etc.), fruit trees and fruits (apples, citrus, pears, persimmons, peaches, peaches, plums, cherry, peach, cherry, almonds, bananas, etc.) , Leaves, fruits and vegetables (cabbage, tomato, spinach, broccoli, lettuce, onion, green onion (Asatsuki, spinach), green pepper, eggplant, strawberry, pepper, okra, leek, etc.), root vegetables (carrot, potato, sweet potato, sweet potato , Daikon, kabu, lentil, burdock, garlic, garlic, etc., processing crops (carp, hemp, beets, hops, sugar cane, sugar beet, olives, gum, Coffee, tobacco, tea, etc.), Uri species (pumpkin, cucumber, watermelon, melon, etc.), grasses (orchard grass, sorghum, timothy, clover, alfalfa, etc.), grasses (Korii grass, bent grass, etc.) , Crops for appreciation such as perfumes (lavender, rosemary, thyme, parsley, pepper, ginger etc.), floriculture (flowers, roses, carnations, orchids, tulips, lily, etc.), garden trees (flowering, cherry blossoms, sweet potato etc.), There can be mentioned plants such as forest trees (Abies sp., Spruce, pines, figs, cedar, mulberry, etc.).

The above “plants” include HPPD inhibitors such as isoxaflutol, ALS inhibitors such as imazethapyr and thifensulfuron methyl, EPSP synthetase inhibitors such as glyphosate, glutamine synthetase inhibitors such as glufosinate, cetoxidim Also included are plants which have been rendered resistant to herbicides such as acetyl-CoA carboxylase inhibitors, bromoxynil, dicamba, 2,4-D, etc. by classical breeding methods or genetic recombination techniques.

Examples of "plants" that have been rendered resistant by classical breeding methods include rapeseed that is resistant to imidazolinone-based ALS-inhibiting herbicides such as imazethapyr, wheat, sunflower, rice, and the trade name of Clearfield (registered trademark). It is already on sale. Similarly, there are soybeans that are resistant to sulfonylurea-based ALS-inhibiting herbicides such as thifensulfuron-methyl by the classical breeding method, and are already sold under the trade name of STS soybeans. Similarly, examples of plants having resistance imparted to acetyl CoA carboxylase inhibitors such as trione oxime type and aryloxyphenoxypropionic acid type herbicides by the classical breeding method include SR corn and the like.
In addition, plants that have been rendered resistant to acetyl CoA carboxylase inhibitors can be treated with Proceedings of the National Academy of Sciences of the United States of America (Proc. Natl. Acad. Sci) USA 87, pp. 7175-7179 (1990), etc. In addition, a mutant acetyl-CoA carboxylase resistant to an acetyl-CoA carboxylase inhibitor is reported in Weed Science, 53, 728-746 (2005) and the like, and such a mutant acetyl-CoA carboxylase gene is It is possible to produce a plant resistant to an acetyl-CoA carboxylase inhibitor by introducing into a plant acetyl-CoA carboxylase a mutation involved in the introduction into a plant or imparting resistance by the above-mentioned method. 1999. A base substitution mutation introduced nucleic acid represented by Repairing the Genome's Spelling Mistakes. Science 285: 316-318. By introducing a site-specific amino acid substitution mutation into the chilli-CoA carboxylase gene, ALS gene, etc., plants resistant to the acetyl-CoA carboxylase inhibitor, ALS inhibitor etc. can be produced. The compound represented by General formula (1) of this invention or its salt can be used.

As weeds that can be controlled using the compound represented by the general formula (1) of the present invention or a salt thereof, the genus of dicotyledonous weeds includes Ipomoea, Izena (Lindernia), American Tsunoxanem (Sesbania), Ichibi (Abutilon), Anemone chaperus (Matricaria), Anemone grass (Rorippa), nettle (Urtica), Lamium (Lamium), Onakomi (Xanthium), Mustard (Sinapis), Rota (Rotala) Scutellariae * Veronica, Papaver (Papaver) ), White clover (Chenopodium), white clover (Trifolium), scorpionfish (Portulaca), violet pansy (Viola), alba asagao (Pharbitis), etc. Solanum), Capsella, Nori Thistle (Cirsium) Norushi (Sonchus) Persimmons (Galinsoga), chickweed (Stellaria), perennial myrtle, myriad mycorrhiza (Senecio), myrtle hagageto (Amaranthus), ragweed (Ambrosia), broom broom (Kochia), moth buffalo (Lamium), moth moth (Leipilium) (Polygonum), Jaem-graa (Galium), Cornflower (Centaurea), Artemisia, etc. may be mentioned.

As genera of monocotyledonous weeds, Leptochloa et al., Red-tailed Timothy (Phleum), Berberis sativus (Phleum), Berriestis snail (Poa), Scutellaria japonicus (Festuca), Echinocora japonica (Setaria), Echinochrea japonica (Eleusine), Omodaka Kwai (Sagittaria), Agropyron (Agropyron), Platypus (Ischaemum), Kyasurigasa papyrus (Cyperus), Oatmugi (Ovem) (Avena), Scutellariae (Bromus), Kivi Ng Guillaria fern (Cynodon), Monarch (Monochoria), Sperm (Alopecurus), Spermella (Paspalum), Tsuyukusa (Commelina), Tenchi (Fimbristylis), Dokumugi (Lolium), Nikukibi (Brachiaria), Nukabo (Agrostis), ), Hie (Echinochlona), Scallop Lee Ukiyagura-thick (Scirpus), crabgrass (Digitaria), sorghum (Sorghum) and the like.

Specific examples of other weeds include Amaranthus retroflexus, Amaranthus viridis, Setaria faberi, Leptochloa chinensis, Azet mustard (Lindernia angistifolia), Azena (Linderia americas, N.). ), American Azena (Lindernia dubia), American Golden-backed Deer (Sida spinosa), American Red-winged Pineapple (Polygonum pensylvanicum), American Black-nosed Neem (Sesbania exaltata), American Fury (Geranium carolinense), Arety-no-sych (Conyza bonariensis), White-backed Gull , Japanese gooseberry (Polygonum cuspidatum), Japanese goby (Abutilon theophrasti), Anemone beetle (Matricaria perforata), Anisei (Polygonum longisetum), Anioglossum (Echinochloa crus-galli), Anemone flower (Amaranthus lividus), Anemone dog (Solanum nigrum) , American beech (Malva sylvestris), American buffalo (Bromus tectorum), Urikawa (Sagittaria pygmaea Miq), Ezonoishiishi (Rumex obtusifolius), Echinochiroshima (Setaria viridis), Cassis obtusifoliich. Watermelon (Xanthium canadens), spinach (Panicum dichotomiflorum), Milkweed (Asclepias syriaca), Scutellariae (Euphorbia maculata), plantain (Plantago asiatica), Tilapia (Amaranthus palmeri), Oryria Avena sterilis), Ehimene (Eleusine indica), Omodaka (Sagittaria trifolia), Euronia cicutarium, Ceram thaliana (Cerastium glomeratum), Orosagiaku (Matricaria matricarioides), Camorelli (Matricaria) chamomilla), common dove (Vicia angustifolia), common dove (Bromus secalinus), common ove (Avena fatua), falcon (Rotala indica Koehne), falcon (Rumex japonicus), falcon (Cyperus esculenta) Pueraria lobata), Eleocharis kuroguwai Ohwi), Ambrosia trifida, Corn Marigold (Chrysanthemum segetum), Kagome Terrier (Cyperus iria), Conch (Monochoria vaginalis), Rhizoctia (Echinithiolacoatlatica) , Weedy rice (Oryza sativa), Sanaeta (Polygonum lapathifolium), Shibamugi (Agropyron repens), Sha-cane (Sorghum vulgare), Silky bentgrass (Apera spica-venti), Shiloza (Chenopodium album), White clover (Trifolium repens) , White-flowered butterfly Senaga O (Datura stramonium), Japanese horsetail (Equisetum arvense), scutellariae (Poa annua), Squirrel broom (Bromus japonicus), Eurasian tree peony (Alopecurus aequalis), scorpion hail (Portulaca oleracea), Seika horse mackerel ), Mustard (Brassica juncea), Dandelion (Taraxacum officinale), European Convolvulus (Convolvulus arvensis), Zenibaa (Malva neglecta), Seri (Oenanthe javanica), Prunella vulgare (Polygonum convolvulus), Tainuidae, Ischaemum rugosum, Veronica arvensis, Cyperus dicorismis L., Talihonoa oganiteu (Amaranthus rudis), Citrus ditades (Ludwigia prostrata Roxburgh), Tussula (Commelina communis), Texas Pani Carp (Panicum texanum), Euphorbia helioscopia, Nagabaishi (Rumex crispus), Nazuna (Capsella bursa-pastoris), Nii-Kishi (Euphorbia pseudochamaesyce), Nikkibi (Brachiaria plantaginea) , Anchovy (Sinapis arvensis), Red-tailed Starch (Galinsoga ciliata), Duckweed (Stelliria media), Hamasule (Cyperus rotundus), Harabiyu (Amaranthus spinosus), Hartade (Polygonum persicaria), Hinagishi (Papaver hoe haus ichus) (Lamium purpureum), Hemokugu (Kyllinga gracillima), Hemisohya dander (Ammannia multiflora), Hemmy mexicorrhea (Conyza canadensis), Heumshiro (Potamogeton distinctum A. Benn), Myrtlefish (Amaranthus tuberculosis)- , Ambrosia artemisiifolia, Veronica hederaefolia, Florida Vega-Wide (Desmodium tortuosum), Planago lanceolata, Hermaphrodite (Alisma canaliculatum A. Br. Et Bouche), Kochi Lolium rigidum), Brentia vulgaris (Amannia coccinea), Bromeliad (Lolium perenne), Scallops (Scirpus juncoides Roxburgh), Scutellariata (Lamium amplexicaule), Scutellariata (Amaranthus hybridus) (Ipomoea lacunosa), Maruba asagao (Ipomoea purpurea), Maruba american asagao (Ipomoea hederacea var integraisucula), Maruba Yuyuka (Commelina bengharensis), Mizuhoi (Monochoria korsakowii), Miho (Digit aria ciliaris), crabgrass (Digitaria sanguinalis), sorghum (Sorghum bicolor), mauve grass (Galium aparine), mugwort (Artemisia princeps), wild pansy-(Viola tricolor), wild radish (Raphanus raphanistrum), forget-me-not (Myosotis arvensis etc. Can be mentioned.

The compound represented by the general formula (1) of the present invention or a salt thereof is generally formulated and used in a form convenient for use according to a conventional method on a pesticide formulation.
That is, the compound represented by the general formula (1) of the present invention or a salt thereof is dissolved, separated, or suspended in a suitable inert carrier, or optionally in combination with an adjuvant in an appropriate ratio. Turbid, mixed, impregnated, adsorbed or attached to a suitable dosage form such as suspension (flowable), emulsion, oil, solution, wettable, water dispersible granule, granule, powder, tablet, pack, It may be formulated into a jumbo agent, a suspoemulsion, etc.

  The herbicide of the present invention can contain, in addition to the active ingredient, an additive component generally used for the herbicide, if necessary. As the additive component, carriers such as solid carrier, liquid carrier, surfactant, dispersant, wetting agent, binder, tackifier, thickener, coloring agent, spreading agent, spreading agent, antifreeze agent And anti-caking agents, disintegrants, anti-degradants and the like. In addition, if necessary, preservatives, plant debris and the like may be used as additives. These additive components may be used alone or in combination of two or more.

  As a solid carrier, for example, natural minerals such as quartz, clay, kaolinite, pyrophyllite, cericite, talc, bentonite, acid clay, attapulgite, zeolite, diatomaceous earth, etc., inorganic salts such as calcium carbonate, ammonium sulfate, sodium sulfate, potassium chloride Organic solid carriers such as synthetic silicic acid, synthetic silicates, starch, cellulose, plant powder (eg sawdust, coconut shell, corn cob, tobacco stem, etc.), plastic carriers such as polyethylene, polypropylene, polyvinylidene chloride, etc., urea, Inorganic hollow bodies, plastic hollow bodies, fumed silica (fumed silica, white carbon) and the like can be mentioned. These may be used alone or in combination of two or more.

  Examples of the liquid carrier include monohydric alcohols such as methanol, ethanol, propanol, isopropanol and butanol, and polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol and glycerin. Alcohols, Polyhydric alcohol compounds such as propylene glycol ether, Ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone etc. Ethyl ether, dioxane, ethylene glycol monoethyl ether, dipropyl ether, THF etc Aliphatic hydrocarbons such as ether, normal paraffin, naphthene, isoparaffin, kerosene, mineral oil, benzene, Aromatic hydrocarbons such as ene, xylene, solvent naphtha and alkyl naphthalene, halogenated hydrocarbons such as dichloromethane, chloroform and carbon tetrachloride, esters such as ethyl acetate, diisopropyl phthalate, dibutyl phthalate, dioctyl phthalate and dimethyl adipate , Lactones such as γ-butyrolactone, amides such as dimethylformamide, diethylformamide, dimethylacetamide, N-alkylpyrrolidinone, nitriles such as acetonitrile, sulfur compounds such as dimethylsulfoxide, soybean oil, rapeseed oil, cottonseed oil, Vegetable oil such as castor oil, water and the like can be mentioned. These may be used alone or in combination of two or more.

  As surfactant used as a dispersing agent or a wetting agent, for example, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, sucrose fatty acid ester, polyoxyethylene fatty acid ester, polyoxyethylene resin acid ester, polyoxyethylene fatty acid diester, Polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene alkyl phenyl ether, polyoxyethylene dialkyl phenyl ether, polyoxyethylene alkyl phenyl ether formalin condensate, polyoxyethylene polyoxypropylene block copolymer, polystyrene polyoxyethylene Block polymer, alkyl polyoxyethylene polypropylene block copolymer ether, polyoxyethylene Alkylamine, polyoxyethylene fatty acid amide, polyoxyethylene fatty acid bisphenyl ether, polyalkylene benzyl phenyl ether, polyoxyalkylene styryl phenyl ether, acetylene diol, polyoxyalkylene addition acetylene diol, polyoxyethylene ether type silicone, ester type Nonionic surfactants such as silicone, fluorosurfactant, polyoxyethylene castor oil, polyoxyethylene hydrogenated castor oil, alkyl sulfate, polyoxyethylene alkyl ether sulfate, polyoxyethylene alkyl phenyl ether sulfate, polyoxy acid Ethylene styryl phenyl ether sulfate, alkyl benzene sulfonate, alkyl aryl sulfonate, lignin sulfonate, alkyl sulfate Succinate, naphthalene sulfonate, alkyl naphthalene sulfonate, salt of formalin condensate of naphthalene sulfonic acid, salt of formalin condensate of alkyl naphthalene sulfonic acid, fatty acid salt, polycarboxylate, polyacrylate, N Anionic surfactants such as -methyl-fatty acid sarcosinate, resin acid salt, polyoxyethylene alkyl ether phosphate, polyoxyethylene alkyl phenyl ether phosphate, laurylamine hydrochloride, stearylamine hydrochloride, oleylamine hydrochloride, Cationic surfactants such as alkylamine salts such as stearylamine acetate, stearylaminopropylamine acetate, alkyltrimethylammonium chloride, alkyldimethylbenzalkonium chloride, etc. Amphoteric interfaces such as amino acid type or betaine type Gender, and the like. These surfactants may be used alone or in combination of two or more.

  Examples of binders and tackifiers include carboxymethylcellulose and salts thereof, dextrin, water-soluble starch, xanthan gum, guar gum, sucrose, polyvinyl pyrrolidone, gum arabic, polyvinyl alcohol, polyvinyl acetate, sodium polyacrylate, average molecular weight 6000 to 20000 Polyethylene glycol, average molecular weight 100,000 to 5,000,000 polyethylene oxide, phospholipid (eg cephalin, lecithin etc.) cellulose powder, dextrin, modified starch, polyaminocarboxylic acid chelate compound, crosslinked polyvinyl pyrrolidone, co-weight of maleic acid and styrenes Combined, (meth) acrylic acid type copolymer, half ester of dicarboxylic acid anhydride with polymer consisting of polyhydric alcohol, water soluble salt of polystyrene sulfonic acid, paraf Emissions, terpene, polyamide resins, polyacrylate, polyoxyethylene, wax, polyvinyl alkyl ethers, alkylphenol-formalin condensates, synthetic resin emulsions, and the like.

  As the thickener, for example, xanthan gum, guar gum, diutan gum, carboxymethylcellulose, polyvinylpyrrolidone, carboxyvinyl polymer, acrylic polymer, starch compound, water soluble polymer such as polysaccharide, high purity bentonite, fumed silica (fumed Inorganic fine powders such as silica, white carbon, etc. may be mentioned.

  Examples of the colorant include inorganic pigments such as iron oxide, titanium oxide and Prussian blue, and organic dyes such as alizarin dye, azo dye and metal phthalocyanine dye.

  Examples of the antifreezing agent include polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol and glycerin.

  Adjuvants for preventing caking or disintegration include, for example, polysaccharides such as starch, alginic acid, mannose and galactose, polyvinyl pyrrolidone, fumed silica (fumed silica, white carbon), ester gum, petroleum resin, sodium tripolyphosphate, Sodium hexametaphosphate, metal salt of stearic acid, cellulose powder, dextrin, copolymer of methacrylic acid ester, polyvinyl pyrrolidone, chelate of polyaminocarboxylic acid, sulfonated styrene / isobutylene / maleic anhydride copolymer, starch / polyacrylonitrile graft copolymer Polymer etc. are mentioned.

  Examples of the decomposition inhibitor include zeolite, fresh lime, desiccant such as magnesium oxide, phenol compound, amine compound, antioxidant such as amine compound, sulfur compound, and phosphoric acid compound, ultraviolet absorber such as salicylic acid compound and benzophenone compound, etc. Be

Examples of the preservative include potassium sorbate, 1,2-benzothiazolin-3-one and the like.
Furthermore, as necessary, other functions such as functional spreading agents, activity enhancers such as metabolic decomposition inhibitors such as piperonyl butoxide, antifreeze agents such as propylene glycol, antioxidants such as BHT, ultraviolet absorbers and the like Agents can also be used.

  The compounding ratio of the active ingredient compound can be adjusted as necessary, and it may be suitably selected from the range of 0.01 to 90 parts by weight in 100 parts by weight of the herbicide of the present invention, for example, dust, In the case of granules, emulsions or wettable powders, 0.01 to 50 parts by weight (0.01 to 50% by weight based on the total weight of the herbicide) is suitable.

  The use amount of the compound represented by the general formula (1) of the present invention or its salts depends on various factors such as purpose, target weed, growth condition of crops, weed development tendency, weather, environmental conditions, dosage form, application method Depending on the application site, application time, etc., the active ingredient compound may be suitably selected from the range of 0.001 g to 10 kg, preferably 0.01 g to 1 kg, per 10 are according to the purpose.

  When using a herbicide containing the compound represented by the general formula (1) of the present invention or a salt thereof as an active ingredient, it is diluted to a suitable concentration and sprayed or applied as it is.

The herbicide containing the compound represented by the general formula (1) of the present invention or a salt thereof as an active ingredient is directly sprayed on the weeds in the weeds, the soil and a cultivation carrier etc. in an effective amount for weed control. It can be used by treating or treating the seeds of useful plants.

The "soil" or "cultivation carrier" of a plant in the case of practicing the method of use of the present invention refers to a support for cultivating a crop, in particular a support for growing roots, and the material is not particularly limited. However, so long as the plant can grow, so-called soil, nursery mat, water, etc. may be used, and specific materials include, for example, sand, pumice, vermiculite, diatomaceous earth, agar, gel-like substance, high It may be a molecular substance, rock wool, glass wool, wood chips, burks, etc.

Treatment to soil and cultivation carrier etc. includes soil whole layer mixing, row application, floor soil mixing, cell seedling treatment, planting hole treatment, stock source treatment, top dress, box treatment of rice, water surface application, etc. .

  As the application method of box processing of rice, the dosage form may differ depending on the application time, such as application at the time of seeding application, planting period application, application at the time of transplanting, etc., but dosage forms such as powders, water dispersible granules, granules You can apply it with. It can also be applied by mixing with the soil, and mixing with the soil, powder, water dispersible granules or granules, for example, mixing with the bed soil, mixing with the soil, mixing into the whole soil, etc. It is also possible to apply layering soil and various preparations alternately in layers.

As a method of water surface application, solid preparations such as jumbo, pack, granules, water dispersible granules and the like, liquid preparations such as flowable, emulsion and the like are usually sprayed on flooded paddy fields. In addition, by using a chemical solution such as emulsion, flowable or the like as the water inflow source to the paddy field such as a water port or an irrigation device, it can be applied laborsaving along with the supply of water.

As a method of seed treatment, immersion of a seed in a drug, seed dressing and carpper treatment, etc. may be mentioned.

The term "seed" for the seed treatment means a plant at an early stage of cultivation used for propagation of the plant, for example, in addition to seeds, bulbs, tubers, seeds, shoots, shoots, stems, or cuttings Plants for vegetative propagation can be mentioned.

The compound or a salt thereof represented by the general formula (1) of the present invention is a weed to be controlled, another herbicide, a plant growth regulator, or a medicinal plant for the purpose of extending a suitable control period or for reducing the dose. It is also possible to use it in combination with agents (also called safeners), soil conditioners, fertilizers, etc., and depending on the use situation, agricultural and horticultural insecticides, acaricides, nematocides, fungicides It is also possible to use it in combination with biological pesticides and the like. Examples of representative compounds are shown below, but the invention is not limited thereto.

Other herbicides used for such purpose include, for example, 1-naphthylacetamide, 2, 4-PA, 2, 3, 6-TBA, 2, 4, 5-T, 2, 4, 5-TB, 2, 4 -D, 2,4-DB, 2,4-DEB, 2,4-DEP, 3,4-DA, 3,4-DB, 3,4-DP, 4-CPA, 4-CPB, 4-CPP MCP, MCPA, MCPA thioethyl, MCPB, ioxynil, aclonifen, azaphenidin, acifluorfen, aciprotryne, aziprotryne, azimsulfuron, asulam, acelam Kroll (acetochlor), atrazine (atrazine), atraton (atraton), anisuron (anisuron), anilophos (anilofos), abiglycine (aviglycine), abscisic acid (abscisic acid), amicarbazone (amicarbazone), amidosulfuron (amidosulfuron), amitrolol (Amitrole), aminocyclopyrachlor (aminocyclopyrachlor), aminopyralid ( aminopyralid), amibuzin (amibuzin), amiprophos-methyl, ametridione (ametridione), ametrine (ametrynone), alachlor (alachlor), allidochlor (allidochlor), alloxydim (alloxydim), allolac (alorac), Offensulfron (iofensulfuron), isouron (isouron), isocarbamide (isocarbamide), isoxachlortol (isoxachlortole), isoxapyrifop (isoxapyrifop), isoxaflutole (isoxaflatole), isoxaben (isoxaben), isosyl (isocil) , Isonoruron, isoproturon, isopropalin, isopolinate, isopolinate, isomethiodine, isomethiozin, inabenfide, inapenfide, ipazine, ipfencarbazone, iprimidam iprymida m) imazaquin (imazaquin), imazapic (imazapic), imazapyr (imazapyr), imazamethapyr (imazamethapyr), imazamethabenz (imazamethabenz), imazamethabenzmethyl (imazamethabenz-methyl), imazamox (imazamox), imazethapyr (imazethaflon r) (Imazosulfuron), indaziflam (indaziflam), indanophan (indanofan), indolebutyric acid (indobutyric acid), uniconazole-P (uniconazole-P), eglinazine (eslinazine), esprocarb (esprocarb), etamessulfuron (ethametsulfuron) Methyl (ethametsulfuron-methyl), etalfluralin (ethalfluralin), ethiolate (ethiolate), ethychlozate ethyl, ethydimuron (ethidimuron), ethynophen (etinofen), ethephon (ethephon), ethoxysulfuron (ethoxysulfo) ron), ethoxyphen (ethyphenid), etnipromid (etnipromid), ethofumesate (ethofumesate), etobenzanide (etobenzanid), epronaz (epronaz), erbon (erbon), endothal (endothal), oxadiazone (oxadiazon), oxadiargyl (oxadiargyl), Oxadiclomefone (oxaziclomefone), oxsulfurone (oxasulfuron), oxapyrazone (oxapyrazoon), oxyfluorfen (oxyfluorfen), oryzalin (oryzalin), orthosulfamuron (orthosulfamuron), orbencarb (orbencarb), cafencetrol (cafenstrole), cambendiclor), carbasulam, carfentrazone, carfentrazone-ethyl, carbutarate, karbutilate, carbetamide, carboxazole (Carboxazole), quizalohop (quizalofop), quizalohop-P (quizalofop-P), quizalohop-ethyl (quizalofop-ethyl), xilachlor (xylachlor), quinoclamine (quinoclamine), quinonamide (quinonamide), quinclorac, quinclorac Lac (quinmerac), cumyluron (cumyluron), cliodinate (clidinate), glyphosate (glyphosate), glufosinate (glufosinate), glufosinate-P (glufosinate-P), credazine (credazine), cretodym (clethodim), croxifonac (cloxyfonac) , Clodinafop (clodinafop), clodinafop-propargyl (clodinafop-propargyl), crotoluron (chlorotoluron), clopyralid (clopyralid), cloproxiym (cloproxydim), cloprop (cloprop), clobromuron (chlorbromuron), cromazon (clofop) clomazone), Chloromethoxyl (chlomethoxyni1), clomethoxyphen (chlomethoxyfen), clomeprop (clomeprop), chlorazifop (chlorazifop), chlorazlam (cloransulam), chloranocryl (chloranocryl), chloramben (chloramben), chloruramlam-methyl methylcyclomethanemethylchloromethane , Chloridazon (chloridazon), chlorimuron (chlorimuron), chlorimuron-ethyl (chlorimuron-ethyl), chlorsulfuron (chlorsulfuron), chlorthal (chlorthal), chlorthiamide (chlorthiamide), chlortoluron (chlortoluron), chlornitrofen (chlornitrofen), chlorfenac (Chlorfenac), chlorfenprop (chlorfenprop), chlorbufam (chlorbufam), chlorflurazole (chlorflurazole), chlorflurenol (chlorflurenol), chlorprocarb (chlorprocarb), chlorprocarb Profham (chlorpropham), chlormequat (chlormequat), chloretron (chloretron), chloroxynil (chloroxynil), chloroxon (chloroxuron), chloropon (chloropon), saflufenacil (saflufenacil), cyanazine (cyanazine), cyanatrine (cyanatylate) ), Diuron (diuron), dietham coat (diethamquat), dicamba (dicamba), cycluron (cycluron), cycloate (cycloate), cycloxidim (cycloxydim), diclosulam (diclosulam), cyclosulfamuron (cyclosulfamuron), cyclopyrimolate ( cyclopyrimorate), dicloprop (dichlorprop), dicloprop-P (dichlorprop-P), diclobenil (diclobenil), diclohop (diclofop), diclohop methyl (diclofop-methyl), dichromate (dichlormate), dichloral urea (dicloralulur) ea), diquat, cisanilide, disul, siduron, dithiopyr, dinitramine, dinitramine, cinidon-ethyl, dinosam, cinosulfuron, Dinoseb, dinoterb, dinofenate, dinoprop, cyhalofop-butyl, diphenamide, difenoxuron, difenopenten, difenzoquat ), Sibutrin (cybutryne), cyprazine (cyprazine), cyprazole (cyprazole), diflufenican (diflufenican), diflufenzopyr, dipropetryn, cypromid (cypromid), cyperquat (giperquat), gibberellin (gibberell) Madazine (simazine), Dimexano (dimexano), Dimethachlor (dimethachlor), Dimedazon (dimidazon), Dimethamethrin (dimethamethryn), dimethenamid (dimethenamid), simetryn (simetryn), simeton (simeton), dimepiperate (dimepiperate) Synmethylin (cinmethylin), Swep, sulglycapin, sulcotrione (sulcotrione), sulferate (sulfallate), sulfentrazone (sulfentrazone), sulfosulfuron (sulfosulfuron), sulfometuron (sulfometuron), sulfometuron methyl (sulfometuron-methyl), sekbumeton (secbumeton), setoxydim (sethoxydim), sebuthylazin (sebuthylazine), terbacil (terbacil), daimuron (daimuron), dazomet (dazomet), dalapon (dalapon), thiazafluron (thiazafluron) Thiazopyr, tiaphenacil, tiencarbazone, thiencarbazone methyl, thiocarbasil, tiocarbazil, thiochlorim, thiobencarb, thidiazimine, Thifensulfuron, thifensulfuron-methyl, desmedipham, desmetryn, tetrafluron, tetrafluron, thenylchlor, tebutam, tebuthiuron, Terbumeton (terbumeton), tepraloxydim (tepraloxydim), tefuryltrione (tefuryltrione), tembotrione (tembotrione), delachlor (delachlor), terbacil (terbacil), terbucarb (terbucarb) Kroll (terbuchlor), terbuthylazine (terbuthylazine), terbuthrin (terbutryn), topramezone (topramezone), tralkoxydim (tralkoxydim), triadiflam (triaziflam), triasulfuron (triasulfuron), triafamone (triafamone), triate tritate (Trietazine), tricamba (tricamba), triclopyr (triclopyr), tridiphane (tridiphane), tritac (tritac), tritosulfuron (tritosulfuron), trifludimoxazine (trifludimoxin), triflusulfuron (triflusulfuron), triflusulfuron methyl (triflusulfuron-methyl), trifluralin (trifluralin), trifloxysulfuron (trifloxysulfuron), tripropindan (tripropindan), tribenuron methyl (tribenuron-methyl), tribenuron (tribenuron), trihop (trifop), Liphopsime, trimeturon, tolpyralate, naptalam, naproanilide, napropamide, nicosulfuron, nicosulfuron, nitralin, nitrofen, nitrofulfen (Nitrofluorfen), nipyraclofen, neburon, norflurazon, noruron, noruron, barban, paclobutrazol, paquat, parafluron, haloxidine ), Haloxifene, haloxyfop, haloxyfop-P, haloxyfop-methyl, halosafen, halosulfuron, halosulfuron, halosulfuron furon-methyl), picloram (picloram), picolinafen (picolinafen), bicyclopyrone (bicyclopyrone), bispyribac (bispyribac), bispyribac sodium (bispyribac-sodium), pidanone (pydanon), pinoxaden (pinoxaden), bifenox (bifenox) , Piperophos, hymexazol, pyraclonil, pyrasulfotole, pyrazoxyfen, pyrazosulfuron, pyrazosulfuron, pyrazosulfuron-ethyl, pyrazolate, pyranazolate, bilanafos), pyraflufen-ethyl, pyriclor, pyridafol, pyrithiobac, pyrithiobac-sodium, pyridate, pyriphthalide , Pyributicarb, pyribenzoxim, pyrimisulfan, pyrimisulfon, primisulfuron, pyriminobac-methyl, pyroxasulfone, pyroxsulam, pyroxsulam, phenasulam ), Phenisophum, phenuron, fenoxasulfone,
Fenoxaprop (fenoxaprop), fenoxaprop-P, fenoxaprop-ethyl, phenothiol (phenothio1), phenoprop (fenoprop), phenobenzuron, fenquinotrione (Fenquinotrione), fenthiaprop (fenthiaprop), fenteracol (fenteracol), fentrazamide (fentrazamide), fenmedipham (phenmedipham), fenmedipham ethyl (phenmedipham-ethyl), butachlor (butachlor), butafenacil (butafenacil), butamiphos (Butamifos), buthiuron, buthidazole (buthidazole), butylate (butylate), buturon (buturon), butenacol (butenachylor), butyodym (butroxydim), butraline (butralin), flazasulfuron (flazasulfuron), flamprop (flamprop) ), Furyloxyphen (fyloxyfen), prinachlor (prynachlor), primisulfuron-methyl (primisulfuron-methyl), fluazifop (fluazifop), fluazifop-P (fluazifop-butyl), fluazifop-butyl, furazolate (Fluazolate), fluroxypyr (fluroxypyr), fluothiouron (fluothiuron), flumeturon (fluometuron), fluoroglycofen (fluoroglycofen), flurochloridon (flurochloridone), fluorodiphen (fluorodifen), fluoro nitrophen (fluoronitrofen), fluoromidine (fluoromidine) ), Flucarbazone (flucarbazone), flucarbazone sodium (flucarbazone-sodium), fluchloralin (fluchloralin), flucetosulfuron (flucetosulfuron), fluthiaset (fluthiacet), fluthiacet methyl (fluthiacet-methyl), flupyrsulfuron (fluthiacret) flupyrasulfuron), flufenacet (flufenacet), flufenican (flufenican), flufenpyr (flufenpyr), flupropacil (flupropacil), flupropanate (flupropanate), flupoxam (flupoxam), flumioxazin (flumioxazin), flumiclorac (flumiclorac) Flumicrolac pentyl (flumiclorac-pentyl), flumipropyne (flumipropyn), flumezin (flumezin), flumeturon, flumethoslam, fluridone, fluritamon, flurtamone, fluroxypyr, Proxan (proxan), proglinazine, procyazine, prodiamine (prodiamine), prosulfalin (prosulfalin), prosulfuron (prosulfuron), prosulfocarb (prosulfocarb), pro Kizahop (propaquizafop), propachlor (propachlor), propadine (propazine), propazyl (propyzamide), propisochlor (propisochlor), prohydrojasmon (prohydrojasmon), propyrisulfuron (propyrisulfuron), propham (propham) ), Profluazole (profluralin), prohexadione calcium (prohexadione-calcium), propoxycarbazone (propoxycarbazone), propoxycarbazone sodium, propoxycarbazone-sodium, profoxydim, bromacil (bromacil) , Brompyrazone (brompyrazon), promethrin (prometryn), prometon (prometon), bromoxynil (bromoxynil), bromophenoxim (bromofenoxim), bromobutide (bromobutide), bromobonil (bromobonil), florasulam (fl orulasula), florpyraxifen, hexachloroacetone (hexachloroacetone), hexazinone (hexazinone), petoxamide (pethoxamid), benazoline (benazolin), penoxsulam, pebulate (pebulate), beflubutamide (beflubutamide) vernolate), perfluidone, bencarbazone, benzadox, benzipram, benzylaminopurine, benzthiazuron, benzthiazuron, benzfendizone, bensulide, bensulide) Ruflon methyl (bensulfuron-methyl), benzoyl prop (benzoylprop), benzobicyclon (benzobicyclon), benzophenap (benzofenap), benzofluor (benzofluor), bentazone (bentazone), pentanok (Pentanochlor), Benthiocarb (benthiocarb), Pendimethalin (pendimethalin), Pentoxazone (Pentoxazone), Benfuralin (Benfluralin), Benfuresate (Benfuresate), Fosamine (Fosamine), Fomesafen, Folamsulfuron (foramsulfuron), Forchlorfenuron (forchlorfenuron), maleic acid hydrazide (maleic hydrazide), mecoprop (mecoprop), mecoprop-P (mecoprop-P), medinoterb (medinoterb), mesosulfuron (mesosulfuron), mesosulfuron methyl (mesosulfuron-methyl), Mesotrione (mesotrione), mesoprazine (mesoprazine), methoprotryne (methoprotryne), metazachlor (metazachlor), methazole (methazole), metazosulfuron (metazosulfuron), methabenzthiazuron (methabenzthiazuron), metamitron (metamitron), metamiho (Metamifop), metam (metam), metalpropaline (methalpropalin), methiouron (methiuron), methiozoline (methiozolin), methiobencarb (methiobencarb), methyldaimron (methyldymron), methoxuron (metoxuron), methosulam (metosulam), Metsulfuron (metsulfuron), methsulfuron methyl (metsu1furon-methy1), metfurazone (metflurazon), metobromuron (metobromuron), metobenzuron (metobenzuron), metmeton (methometon), metolachlor (metolachlor), meribuzin (metribuzin), mepicortide mepiquat-chloride), mefenacet (mefenacet), mefluidide (mefluidide), monalide (monalide), monisouron (monisouron), monuron (monuron), monochloroacetic acid (monochloroacetic acid), monolinuron (monolinuron), molinate (molinate) Morpham coat (morfamquat), iodosulfuron (iodosulfuron), iodosulfuron methyl sodium (iodosulfuron-methyl-sodium), iodobonyl (iodobonil), iodomethane (iodomethane), lactofen (lactofen), linuron (linuron), rimsulfuron (limosulfuron) Examples include rimsulfuron), lenacil, rhodethanil, calcium peroxide, methyl bromide and the like.

Other agricultural and horticultural insecticides, acaricides, nematocides used for similar purposes, for example
3,5-xylyl methylcarbamate (XMC), Bacillus thuringiensis aizawaii, Bacillus thuringiensis israelensis, Bacillus thuringiensis japonensis, Bacillus thuringiensis kurstaki, Bacillus thuringiensis tenebrionis, crystalline protein toxin produced by Bacillus thuringiensis, BPMC, Bt-toxin based PCBC Chlorfenson), DCIP (dichlorodiisopropyl ether), DD (1, 3-Dichloropropene), DDT, NAC, O-4-dimethylsulfamoylphenyl O, O-diethylphosphorothioate (DSP), O-ethyl O-4-nitrophenyl phenylphosphonate (EPN), tripropylisocyanurate (TPIC), acrinathrin (acrinathrin), azadirachtin (azadirachtin), azinphos-methyl, acequinocyl, acetamiprid, acetoprole, acetoprole, avemectin (abamectin) ), Afidopyropen, avermectin (avermectin-B), amidoflumet (amidoflumet), amitraz (amitraz), aranicalb (a) lanycarb), aldicarb (aldicarb), aldoxycarb (aldoxycarb), aldrin (aldrin), alpha-endosulfan (alpha-endosulfan), alpha-cypermethrin (alpha-cypermethrin), albendazole (albendazole), allthrin (allethrin), isazophos ( (isazofos), isamidophos (isamidofos), isoamidophos (isoamidofos), isoxathion (isoxaphos), isofenphos (isofenphos), isoprocarb (isoprocarb: MIPC), epsilon-metofluthrin, epsilon-momfluorothrin, ivermectin (ivermectin imino, imidac 1 oprid), imiprothrin (imiprothrin), indoxacarb (indoxacarb), esfenvalerate (esfenvalerate), ethiophen carb (ethiofencarb), ethion (ethion), ethiprole (ethiprole), etoxazole (etoxazole), etofenprox (ethofosprox) (ethopro phos), etlimphos (etrimfos), emamectin (emamectin), emamectin benzoate (emamectin-benzoate), endosulfan (endosulfan), enpentrin (empenthrin), oxamyl (oxamyl), oxydimeton methyl (oxydemeton-methyl), oxydeprofos ( (oxydeprofos: ESP), oxybendazole (oxibendazole), oxfendazole (oxfendazole), potassium oleate (Potassium oleate), sodium oleate (sodium iodide), kadusaphos (cadusafos), kappa-bifenthrin, cartap (cartap), carbaryl (carbary 1), carbosulfan (carbosulfan), carbofuran (carbofulyl), gamma cyhalothrin (gamma-cyhalothrin), xylylcarb (xylylcarb), quinalphos (quinalphos), quinoprene (kinoprene), quinomethionate (chinomethionat), cloetocarb (cloethocab) , Clothianidin, clofenthezine, Lomafenozide (chromafenozide), chlorantraniliprole (chlorantraniliprole), chlorethoxyphos (chlorethoxyfos), chlordimeform (chlordimeform), chlordane (chlordane), chlorpyrifos (chlorpyrifos), chlorpyrifos-methyl (chlorpyrifos-m ethyl), Chlorfenson (chlorfenson), chlorfenbinphos (ch1orfenvinphos), chlorfluazuron (chlorfluazuron), chlorbenzilate (chlorobenzilate), chlorobenzoate (chlorobenzolate), chloroprallethrin, chulsen (dicofol), salithion (salithion), cyhalodiamide, cyanophos (cyanophos: CYAP), diafenthiuron (diafenthiuron), diamidafos (diamidafos), cyantraniliprole (cyantraniliprole), theta-cypermethrin (theta-cypermethrin), dienochlor (dienochlor), cienopyranene (cyenopyrene) The Xabenzophos (dioxabenzofos), diofenolan (diofenolan), sigma-cypermethrin (sigma-cypermethrin), cyclaniliprole, diclofenthion (dichlofenthion: ECP), cycloprothrin (cycloprothrin), dichlorvos (dichlorvos: DDVP), disulfothiol, ), Cyhalothrin (cyhalothrin), cyphenothrin (cyphenthrin), cyfluthrin (cyfluthrin), diflubenzuron (diflubenzuron), cyflumethophene (cyflumetofen), diflovidazine (diflovidazin), cyhexatin (cyhexatin), cypermethrin (cypermethrin), dimethylvinphos , Dimethoate, dimefluthrin, difafluthrin, silafluofen, cyromazine, spinetoram, spinosad, spinosad, spirodiclofen, spiroditrafen, spirotetramat Siphen (spiromesifen), sulfluramid (sulfluramid), sulprofos (sulprofos), sulfoxaflor (sulfofaflor), zeta-cypermethrin (zeta-cypermethrin), diazinon (diazinon), taufluvalinate (tau-fluvalinate), dazomet (dazomet) , Thiacloprid, thiamethoxam, tioxazafen, thiodicarb, thiocyclam, thiosultap, thiosultap, thiosultap-sodium, thionazine, thiomethone, thiomethone deet), dieldrin, tetrachlorvinphos (tetrach1 or vinphos), tetradiphone (tetradifon), tetranitriple, tetramethylfluthrin, tetramethrin, tetrabuprin (tebupirimfos), tebufenozide, , Teful Phosphorus (tefluthrin), teflubenzuron (teflubenzuron), demeton-S-methyl (demeton-S-methyl), temephos (temephos), deltamethrin (deltamethrin), terbuphos (terbufos), tralopyril (tralopyril), tralomethrin (tralomethrin), transfulh Tolu (transfluthrin), Triazamate (triazamate), Triazuron (triazuron), Trichlorfon (trichlamide), Trichlorfon (Trichlorphon: DEP), Triflumezopyrim, Triflumuron, Trifenmurad, Tolfenpyrad, Nared (B), Nithiazine , Nitenpyram (novanpyram), novaluron (novaluron), noviflumuron (noviflumuron), hydroprene (hydroprene), vaniliprole (vaniliprole), vamidothion, parathion (parathion), parathion-methyl (parathion-methyl), halfenprox ( halfenprox), halofenozide, bis Rifluron (bistrifluron), bisultap, hydramethylnon (hydramethylnon), hydroxypropyl starch (hydroxypropyl starch), binapakryl (binapacryl), piflumubide (pyflubumide), bifenazate (bifenazate), bifenthrin (bifenthrin), pimetrozidine , Pyraclorfos, pyrafluprole, pyridafenthion, pyridaben, pyridalyl, pyridalyl, pyrifluquinazon, pyriprole, pyriproxyfen, pyriproxyfen Pyrimidifen (pyrimidofen), pyriminostrobin, pyrimiphos methyl (pirimiphos-methy1), pyrethrin (pyrethrins), fipronil (fiproni1), phenazaquin (fenazaquin), fenamiphos (fenamiphos), phenisobromolate (bromopropylate), fenitrothion (fenitrothion: MEP), fenoxycarb, phenothiocarb, phenothrin, phenobucarb, phensulfothion, phenthion (MPP), phenthoate (PAP), phenvalerate (fenvalerate) , Fenpyroximate, fenpropathrin, fenbendazole, fenbendazole, fosthiazate, formetanate, formetanate, butathiofos, buprofezin, furathiocarb, prallethrin ), Fluacrypyrim, fluazaindolizine, fluazinam, fluazuron, fluensulfone, fluxametamide, flucycloxuron, flucythrinate, fluvalinate, fluviprole , Flupyradifurone, flupyrazophos, flufenerim, flufenoxystrobin, flufenoxuron, flufenzine, flufenoprox, fluproxyfen, fluproxyfen, flubrocythinate, flubrocythrinate, fluhexafon, flubendiamide, flumethrin, flurimfen, prothiofos, prothiofos, protrifenbute, flonicamid, flonamid, propaphos, propargite: BPPS, profenofos (profenofos), profluthrin (profluthrin), propoxur (PHC), flometoquin, bromopropyrate (bromopropylate), beta-cyfluthrin (beta-cyfluthrin), hexaflumuron (hexaflumuron), hexythiazox (hexythiazolox), heptafliothrin, heptenophos), pell Trin (permethrin), benclothiaz, bendiocarb (bendiocarb), bensultap (bensu1tap), benzoximate (benzoximate), benfracarb (benfuracarb), phoxim (phoxim), fossiazet (fosthiazole), fosthiotane ( ), Phosphamidon (phosphamidon), phosphocarb (phosphocarb), phosmet (phosmet: PMP), polynactin complex (polynactins), formetanate (formetanate), formothione (formothion), phorate (phorate), machine oil (machine oil), malathion (malateon) malathion), milbemycin, milbemycin-A, milbemectin, mecarbam, mesulfenphos, meshomfenfos, methaldehyde, metaldehyde, metaflumizone, metamimidophos ), Metam ammonium (metam-ammoniu m) metam-sodium, methiocarb, methidathion (DMTP), methylisothiocyanate, methylneodecanamide, methylparathion, methoxadiazone Methoxychlor (methoxychlor), methoxyphenozide (methoxyfenozide), methofluthrin (metofluthrin), methoprene (methoprene), metolcarb (metolcarb), melfluthrin (meperfluthrin), mevinphos (mevinphos), monocrotophos (monocrotophos), monosultap (monosultap), Cyhalothrin (lambda-cyhalothrin), ryanodine (ryanodine), lufenuron (lufenuron), rescalure, resmethrin (resmethrin), lepimectin (lepimectin), rotenone (rotenone), levamisol hydrochloride (levamisol hydrochloride), oxidized fenbutatin oxide Morantel tartarate, methyl bromide, tricyclohexyltin hydroxide, calcium cyanamide, calcium polysulfide, sulfur, and nicotine- Sulfate) etc. can be illustrated.

Examples of agricultural and horticultural fungicides used for the same purpose include aureofungin, azaconazole, azithiram, acipetacs, acibenzolar, and acibenzolar-S-methyl. ), Azoxystrobin (azoxystrobin), anilazine (anilazine), amisulbrom (amisubulrom), ampropylphos (ampropylfos), ametoctradin, alil alcohol (allyl alcohol), aldimorph (aldimorph), ambam (amobam), isothianyl (Isotianil), isovaledione, isopyrazam, isofetamide, isoproteamido, isoprothiolane, ipconazole, iprodione, iprovaricarb, iprobenphoss (iprobenfoss) ), Imazalil (imazalil), iminoctadine (iminoctadine), iminoctadine albesylate salt (iminoctadine-albesilate), iminoctadine acetate (iminoctadine-triacetate), imibenconazole (imibenconazole), uniconazole (uniconazole), uniconazole P (uniconazole P ), Echromezole, Edifenphos, Etaconazole, Ethaboxam, Ethilimol, Ethem, Ethequin, Ethoxyquin, Etridiazole, Esestirobrine Sastrobin (enoxastrobin), enoxastrobin (enoxastrobin), epoxiconazole (epoxiconazole), oxadixyl (oxadixyl), oxathiapiprolin (oxathiapiprolin), oxathiapiprolin (oxathiapiprolin), oxycarboxin (oxycarboxi) n) Oxyquinoline copper (copper-8-quinolinolate), oxytetracycline (oxytetracycline), oxine copper (copper-oxinate), oxpoconazole (oxpoconazole), oxpoconazole fumarate (oxpoconazole-fumarate), oxolinic Soil fungicides such as oxolinic acid, octhilinone, ofurace, orisastrobin, metam-sodium, kasugamycin, carbamorph, carpropamid, carbendazim (Carbendazim), carboxin, carvone, quinazamide, quinacetol, quinoxytol, quinoxyfen, quinomethionate, quinomethionate, captafol, captan (captan) ), Kiraraxil (kira laxyl), quinconazole (quinconazole), quintozene, guazatine, guafrane, cufraneb, cuprobam, coxoxystrobin, glyodine (glyodin), griseofulvin, climbazole (climbazole) ), Cresol (cresol), cresoxim methyl (kresoxim-methyl), clozolinate (chlozolinate), clotrimazole (clotrimazole), clovenazone (chlobenthiazone), chloraniformemethane (chloraniformethan), chloranil (chloranil), chlorquinox ( chlorquinox), chloropicrin, chlorfenazole, chlorodinitronaphthalene, chlorothalonil, chloroneb, chloroanib, salicylanilide, zarilami (zarilami) d) Cyazofamid (cyazofamid), diethyl pyrrolocarbonate (diethyl pyrocarbonate), dietofencarb (dithofencarb), cyclafuramid (cyclafuramide), cyclocymet (diclocymet), diclozoline (dichlozoline), diclobutrazol (diclobutrazol) dichlofluanid), cycloheximide, diclomezine, dichloran, dichloran, dichlorophen, dichlone, disulfirom, disulfiram, ditalimfos, ditalonif, dithianon, dinicotine M (diniconazole-M), zineb (zineb), dinocap (dinocap), dinocton (dinocton), dinosulfone (dinosulfon), dinoterbon (dinoterbon), dinobuton (dinobuton), dinopenton (dinopenton), Pimethitron (dipymetitrone), dipimethitron (dipymethione), dipyrithione (dipyrithione), diphenylamine (diphenylamine), difenoconazole (difenoconazole), cyflufenamide (cyflufenamid), diflumetorim (diflumetorim), cyproconazole (cyproconithylium, ), Cipendazole (cypendazole), simeconazole (simeconazole), dimethylymol (dimethirimol), dimethomorph (dimethomorph), shimoxanil (cymoxanil), dimoxistorobin (dimoxystrobin), ziram (ziram), silthiofam (silthiofam), Spiroxamine (Spiroxamine), Sultropene (Sultropen), Sedaxane (sedaxane), Zoxamide (zoxamide), Dazomet (dazomet), Thiadiazine (thiadiazin), Thiazinyl tiadinil), thiadifluor (thiadifluor), thiabendazole (thiabendazole), tioximido (tioxymid), thiochlorfenfim (thiochlorfenphim), thiophanate (thiophanate), thiophanate methyl (thiophanate-methyl), thiofluzamide (thiofluzamide), thisiophene, Thioquinox), Thiram (thiram), Decafentin, Decnazene, Teclozeneal, Teclofalam, Tecoram, tetraconazole, tetracarbazole, dehydroacetic acid, tebuconazole tebuconazole), tebufloquin, dodicin, dodine, dodecylbenzenesulfonic acid bisethylenediamine copper complex (II) (DBEDC), dodemorph, dorazoxolon Triadimenol, triadimefon, triazbutil, triazoloxide, triamiphos, triarimol, triarimol, trichlamide, triclopyricarb, tricycliazole, tricycliazole , Triticonazole (triticonazole), tridemorph (tridemorph), tributyltin oxide (tributyltin oxide), triflumizole (triflumizole), trifloxystrobin (trifloxystrobin), trifolin (triforine), tolyl flulanide (tolylfluanid), tolclophophos methyl methyl (Tolclofos-methyl), tolprocarb (tolprocarb), natamycin (natamycin), nabam (nabam), nitrostyrene (nitrostyrene), nitrotasal isopropyl (nitrothal-isopropyl), nuarimol (nuarimol), nonylfe Copper copper (copper nonylphenol sulfonate), halacrinate (halacrinate), validamycin (validamycin), valifenalato (valifenalate), harpin protein (harpin protein), picalbutrazox (picarbutrazox), bixafen (bixafen), picoxystrobin (Picoxystrobin), picobenzamide, picolon (bithionol), bitertanol (bitertanol), hydroxyisoxazole (hydroxyisoxazole), hydroxyisoxazole potassium (hydroisoxazole-potassium), binapacryl (binacapacryl), biphenyl (biphenyl), piperaline piperalin, hymexazol, pyraoxystrobin, pyracarbolid, pyraclostrobin, pyradiflumid, pyrazophos, pyramethophos (Pyrametostrobin), pyriophenone (pyriofenone), pyridinitril (pyridinitril), pyridoflumethophene (pydiflumetofen), pyridoflumethofen (pydiflumetofen), pyrisoxazole (pyrisoxazole), pyrifenox (pyrifenox), pyribencarb (pyribencarb), pyriphencarb (pyribencarb), Pyrimethanil), Pyroxychlor, Pyroxyfur, Pyroquilon, Pyrcloquilon, Vinclozolin, Famoxadone, Fenapanil, Fenamidone, Feminaminosulfine, Phenarimol (fenarimol), fenitropan (fenitropan), phenoxanyl (fenoxanil), ferimsone (ferimzone), felbam (ferbam), fentin (fentin), fenpiclonil (fenpiclonil), fenpi Razamin (fenpyrazamine), fenbuconazole (fenbuconazole), fenfuram (fenfuram), fenpropidin (fenpropidin), fenpropimorph, fenhexamid (fenhexamid), phthalide (phthalide), butiobate (buthiobate), butylamine (butylamine) butylamine, bupirimate, fuberidazole, blasticidin-S, furametopyr, furalaxyl, fluacrypyrim, fluazinam, fluoxastrobin Fluotrimazole, fluopicolide, fluopyram, fluoroimide, flurocarbanil, furcarbanil, fluxapiroxad, fluquinconazole, fluquinaconazole, Luconazole (furconazole), fluconazole-cis (furconazole-cis), fludioxonil (fludioxonil), flusilazole (flusilazole), flusulfamide (flusulfamide), flutianil (flutianil), flutolanil (flutolanil), flutriaphor (flutriafol), furfural (furfural) , Flumecyclox (furmecyclox), flumetbell (flumetover), flumorph (flumorph), proquinazid (proquinazid), prochloraz (prochloraz), procymidone (procymidone), prothiocarb (prothiocarb), prothioconazole (prothioconazole), propamocarb (propomocarb) , Propiconazole (propiconazole), propineb (propineb), flophanate (furophanate), probenazole (probenazole), bromuconazole (bromuconazole), hexachlorobutadiene (hexachlorobutadiene) , Hexaconazole (hexaconazole), hexylthiophos (hexylthiofos), betoxazine (bethoxazin), benalaxyl (benalaxyl), benalaxyl M (benalaxyl-M), benodanyl (benodanil), benomyl (benomyl), peflazoate (pefurazoate quino) ), Penconazole (penconazole), benzamorf (benzamorf), penccuron (pencycuron), benzohydroxamic acid (benzohydroxamic acid), benzobin diflupyr (benzovindiflupyr), benthalron (bentaluron), benzazole (benthiazole), bench abial ibu-isopropyl (benthiavalica b-isopropyl), penthiopyrad (penthiopyrad), penflufen (penflufen), boscalid (boscalid), phosdiphen (phosdiphen), fosetyl (fosetyl), fosetyl aluminum (fosetyl-Al), polyoxins (polyoxins), poly Xolin (polyoxorim), polycarbamate (polycarbamate), folpet (formaldehyde), machine oil (machine oil), maneb (maneb), mancozeb (mancozeb), mandipropamide (mandipropamid), mandestorobin (mandestrobin) Microzolin (myclozolin), myclobutanil (myclobutanil), mildiomycin (mildiomycin), milneb (milneb), mecalbind (mecarbin)
zid), methasulfocarb, metazoxolon, metam, metam-sodium, metalaxyl, metalaxyl, metalaxyl-M, methiram, methylisothi Ocianate (methyl isothiocyanate), methyldinocup (mepthyldinocap), metconazole (metconazole), methosulfoxax (metsufovax), methofroxam (methfuroxam), metominostrobin (metominostrobin), metraphenone (metrafenone), mepanipirim (mepanipoimem) mefenoxam), meptyldinocap, mepronil (mepronil), mebenil (mebenil), methyl iodide (iodomethane), rabenzazole (rabenzazole), methyl bromide (methyl bromide), benzalkonium chloride (benzalkonium chloride), Basic copper chloride (basic cop Inorganic germicides such as basic chloride (basic copper sulfate) and metallic silver (silver), sodium hypochloroate, cupric hydroxide, sulfur sulfide wettable sulfur), calcium polysulfide, potassium hydrogen carbonate, sodium hydrogen carbonate, inorganic sulfur, copper sulfide anhydride, dimethyldithiocarbamic acid Examples are copper compounds such as nickel (nickel dimethyldithiocarbamate), 8-hydroxyquinoline copper (oxine copper), zinc sulfate (zinc sulfate), copper sulfate pentahydrate (copper sulfate pentahydrate) and the like.

  In addition, as biological pesticides, for example, nuclear polyhedrosis virus (NPV), granulosis virus (GV), cytosolic polyhedrosis virus (CPV), insect poxvirus (Entomopoxi virus, EPV) And the like, virus preparations such as monocrosporium phymatopagum (Monacrosporium phytophagum), Steina-nema-carpocapsae (Steinernema carpocapsae), Steina-nema-kushidae (Steinernema kushidai), pesticidal insecticidal agents such as Pasteuria penetrans (Pasteuria penetrans) Microbial pesticides used as agents, Trichoderma lignorum, Agrobacterium radiobacter (Agrobacterium radiobactor), nonpathogenic Erwinia carotovora (Erwinia carotovora), fungicides such as Bacillus subtilis (Bacillus subtilis) use Microbial pesticides, by using mixed such as biological pesticides utilized as herbicides, such as Xanthomonas campestris (Xanthomonas campestris), the same effect can be expected.

  Furthermore, as biopesticides, for example, the green-billed wasp (Encarsia formosa), the coleman's wasp (Aphidius colemani), the spiny fly (Aphidoletes aphidimyza), the isaair hide wasp (Diglyphus isaea), and the leafminer mayfly (Dacnusa sibitica) (E) persimilis, Amblyseius cucumeris, Orius sauteri, and other natural enemies, and Beauveria brongniartii, etc., microbial pesticides, (Z) -10-tetradecenyl acetate, (E, Z) ) -4,10-tetradecazinyl acetate, (Z) -8-dodecenyl acetate, (Z) -11-tetradecenyl acetate, (Z) -13-icosene-10-one, 14-methyl-1 -It is also possible to use in combination with pheromone agents such as octadecene .

  Hereinafter, representative examples of the present invention will be illustrated, but the present invention is not limited thereto.

Production Example 1
Preparation of N- (2-Fluorophenyl) -3-oxo-1- (3- (trifluoromethyl) phenyl) hexahydro-1H-pyrrolidine-2-carboxamide (Compound No. I-2)
2-Fluoroaniline (0 mL) in a solution of 3-oxo-1- (3- (trifluoromethyl) phenyl) hexahydro-1H-pyrrolidine-2-carboxylic acid (0.25 g, 0.80 mmol) in chloroform (5 mL) 11 g (0.96 mmol) and triethylamine (0.24 g, 2.4 mmol) were added, and 50% propylphosphonic anhydride in ethyl acetate (0.76 g, 1.2 mmol) was slowly added dropwise thereto. After stirring for 1 hour at room temperature, water and chloroform were added to the reaction solution to quench the reaction. The organic layer was separated by a liquid separation operation, and the remaining aqueous layer was extracted with chloroform and added to the organic layer. The resulting crude reaction solution was washed with saturated brine and dried by adding anhydrous sodium sulfate. After concentration under reduced pressure using a rotary evaporator, the residue was purified using silica gel column chromatography to give the title compound (0.25 g).
Yield: 77%
Physical property value: Refractive index (nD) 1.4593 (19.1 ° C)

Production Example 2
Preparation of N- (2-fluorophenyl) -1-phenyloctahydroindolizine-2-carboxamide (Compound No. II-1)
2-Fluoroaniline (0.13 g, 1.2 mmol) and triethylamine (0.30 g, 3) in a solution of 1-phenyloctahydroindolizine-2-carboxylic acid (0.26 g, 1.0 mmol) in chloroform (5 mL) .0 mmol) was added, and 50% propyl phosphonic acid anhydride ethyl acetate solution (0.96 g, 1.5 mmol) was slowly added dropwise thereto. After stirring for 1 hour at room temperature, water and chloroform were added to the reaction solution to quench the reaction. The organic layer was separated by a liquid separation operation, and the remaining aqueous layer was extracted with chloroform and added to the organic layer. The resulting crude reaction solution was washed with saturated brine and dried by adding anhydrous sodium sulfate. After concentration under reduced pressure using a rotary evaporator, the residue was purified using silica gel column chromatography to give the title compound (0.28 g).
Yield: 79%
Physical property value: Melting point 134-136 ° C

Reference Example 1
Preparation of dimethyl 2- (3-trifluoromethylbenzylidene) malonate
Dimethyl malonate (4.76 g, 36 mmol) and piperidine (0.51 g, 6 mmol) were added to a solution of 3-trifluoromethylbenzaldehyde (5.22 g, 30 mmol) in toluene (30 mL), and heated under reflux with a Dean-Stark apparatus. The mixture was stirred for 6 hours while dewatering with After allowing to cool, the obtained crude reaction solution was concentrated under reduced pressure using a rotary evaporator, and the residue was purified using silica gel column chromatography to obtain the title compound (6.0 g).
Yield: 69%

Reference Example 2
Preparation of dimethyl 2-((1H-pyrrol-2-yl) (3- (trifluoromethyl) phenyl) methyl) malonate
Pyrrole (3.35 g, 50 mmol), gadolinium (III) triflate (0.60 g, 1.0 mmol) in a solution of dimethyl 2- (3-trifluoromethylbenzylidene) malonate (2.88 g, 10 mmol) in tetrahydrofuran (20 mL) ) Was added and stirred at room temperature for 2 hours. The reaction was quenched by adding water and ethyl acetate to the reaction solution, and the organic layer was separated by liquid separation operation. The aqueous layer was extracted with ethyl acetate and added to the organic layer. The resulting crude reaction solution was washed with saturated brine and dried by adding anhydrous sodium sulfate. After concentration under reduced pressure using a rotary evaporator, the residue was purified using silica gel column chromatography to give the title compound (2.3 g).
Yield: 65%

Reference Example 3
Preparation of methyl 3-oxo-1- (3- (trifluoromethyl) phenyl) -2,3-dihydro-1H-pyrrolidine-2-carboxylate
A solution of dimethyl 2-((1H-pyrrol-2-yl) (3- (trifluoromethyl) phenyl) methyl) malonate (1.78 g, 5.0 mmol) in tetrahydrofuran (10 mL) under ice-cooling 60% sodium hydride (0.30 g, 7.5 mmol) was added little by little and stirred for 1 hour after returning to room temperature. The reaction solution was slowly poured into ice water, water and ethyl acetate were added, and the organic layer was separated by a liquid separation operation. The aqueous layer was extracted with ethyl acetate and added to the organic layer. The resulting crude reaction solution was washed with saturated brine and dried by adding anhydrous sodium sulfate. After concentration under reduced pressure using a rotary evaporator, the obtained residue was purified using silica gel column chromatography to give the title compound (1.1 g).
Yield: 68%

Reference Example 4
Preparation of methyl 3-oxo-1- (3- (trifluoromethyl) phenyl) hexahydro-1H-pyrrolidine-2-carboxylate
5% Pd-C (0.10 g) is suspended in ethyl acetate (10 mL) where 3-oxo-1- (3- (trifluoromethyl) phenyl) -2,3-dihydro-1H-pyrrolidine Methyl 2-carboxylate (0.97 g, 3.0 mmol) was added and stirred for 3 hours in the presence of 4 atm of hydrogen gas. After filtering off Pd-C by Celite filtration, the resulting crude reaction solution was dried by adding anhydrous sodium sulfate. After concentration under reduced pressure using a rotary evaporator, the residue is purified using silica gel column chromatography to obtain the two diastereomers of the title compound (diastereomer 1 (0.35 g), diastereomer 2 (0 .33g)) was obtained.
Diastereomer 1 Yield: 36% (Rf small)
Diastereomer 2 Yield: 33% (Rf value large)

Reference Example 5
Preparation of 3-oxo-1- (3- (trifluoromethyl) phenyl) hexahydro-1H-pyrrolidine-2-carboxylic acid
The methyl 3-oxo-1- (3- (trifluoromethyl) phenyl) hexahydro-1H-pyrrolidine-2-carboxylate obtained in the above Reference Example 4 of Diastereomer 1 (0.30 g, 1.0 mmol) To a solution of ethanol (5 mL) was added 0.5 N aqueous solution of sodium hydroxide (3 mL, 1.5 mmol) and stirred at room temperature for 1 hour. The reaction solution was concentrated under reduced pressure using a rotary evaporator, water and ethyl acetate were added to the residue, and the organic layer was separated by a liquid separation operation. The remaining aqueous layer was acidified with 10% aqueous hydrochloric acid and extracted with ethyl acetate to obtain a crude reaction solution. The crude reaction solution was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure using a rotary evaporator to give the title compound (0.25 g).
Yield: 80%

Reference Example 6
Preparation of dimethyl 2- (pyridine-2-methylene) malonate

Dimethyl malonate (7.27 g, 55 mmol), piperidine (0.43 g, 5.0 mmol) and benzoic acid (0.37 g, 3) in a solution of 2-pyridinecarbaldehyde (5.36 g, 50 mmol) in toluene (50 mL) .0 mmol) was added, and the mixture was stirred for 3 hours while dehydrating using a Dean-Stark apparatus while heating under reflux. After allowing to cool, the obtained crude reaction solution was concentrated under reduced pressure using a rotary evaporator, and the residue was purified using silica gel column chromatography to obtain the title compound (10.2 g).
Yield: 92%

Reference Example 7
Preparation of dimethyl 2- (phenyl (pyridin-2-yl) methyl) malonate
To a solution of dimethyl 2- (pyridine-2-methylene) malonate (5.0 g, 22.6 mmol) in tetrahydrofuran (10 mL) was slowly added dropwise a 1.0 M solution of phenylmagnesium bromide in tetrahydrofuran (34 mL, 33.9 mmol), After completion of the dropwise addition, the mixture was stirred for 2 hours at the same temperature. The reaction solution was slowly poured into ice water, water and ethyl acetate were added, and the organic layer was separated by liquid separation operation. The aqueous layer was extracted with ethyl acetate and added to the organic layer. The resulting crude reaction solution was washed with saturated brine and dried by adding anhydrous sodium sulfate. After concentration under reduced pressure using a rotary evaporator, the residue was purified by column chromatography to give the title compound (5.85 g).
86% yield

Reference Example 8
Preparation of methyl 1-phenyloctahydroindolizine-2-carboxylate
Platinum oxide (0.30 g) is suspended in acetic acid (10 mL), to which dimethyl 2- (phenyl (pyridin-2-yl) methyl) malonate (2.99 g, 10 mmol) is added, and 4 atmospheres of hydrogen gas It stirred in presence for 3 hours. Platinum oxide was filtered off, and the obtained filtrate was concentrated under reduced pressure using a rotary evaporator. Water and ethyl acetate were added to the remaining residue, and the organic layer was separated by a liquid separation operation. The remaining aqueous layer was extracted with ethyl acetate and added to the organic layer. The resulting crude reaction solution was washed with saturated brine and dried by adding anhydrous sodium sulfate. After concentration under reduced pressure using a rotary evaporator, the residue was purified by column chromatography to give the title compound (1.1 g).
Yield: 40%

Reference Example 9
Preparation of methyl 1-phenyloctahydroindolizine-2-carboxylate
To a solution of methyl 1-phenyloctahydroindolizine-2-carboxylate (1.0 g, 3.66 mmol) in ethanol (5 mL) was added 1.46 N aqueous sodium hydroxide solution (3 mL, 4.39 mmol), and 1 at room temperature. Stir for hours. The reaction solution was concentrated under reduced pressure using a rotary evaporator, water and ethyl acetate were added to the residue, and the aqueous layer was separated by a liquid separation operation. The aqueous layer was acidified with 10% aqueous hydrochloric acid and extracted with ethyl acetate to obtain a crude reaction solution. The crude reaction solution was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure using a rotary evaporator to give the title compound (0.75 g).
Yield: 79%

  Examples of formulations are shown below, but are not limited thereto. In the formulation examples, "parts" indicates parts by weight.

Formulation Example 1
The compound represented by the general formula (1) of the present invention 10 parts Xylene 70 parts N-methylpyrrolidone 10 parts Mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzene sulfonate 10 parts The above are uniformly mixed and dissolved to obtain an emulsion Do.

Formulation Example 2
The compound represented by the general formula (1) of the present invention 3 parts Clay powder 82 parts Diatomaceous earth powder 15 parts The above are uniformly mixed and pulverized to obtain a powder.

Formulation Example 3
Compound represented by the general formula (1) of the present invention 5 parts Mixed powder of bentonite and clay 90 parts Calcium lignin sulfonate 5 parts The above are uniformly mixed, an appropriate amount of water is added and kneaded, granulated and dried It is made into granules.

Formulation Example 4
Compound represented by the general formula (1) of the present invention 20 parts Kaolin and synthetic highly dispersed silicic acid 75 parts Mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzene sulfonate 5 parts The above are uniformly mixed and pulverized and wettable I assume.

Test Example 1 Post-emergence herbicidal efficacy test for paddy weeds.
A compound represented by the general formula (1) of the present invention, prepared according to Formulation Examples 1 to 4 after seeding barnyard grass, Anopheles spp. Were diluted with water so as to obtain a predetermined concentration of the active ingredient, and dropped. Then, the herbicidal effect was evaluated according to the following criteria in comparison with the non-treated area after 6 days of drug treatment by growing at 30 ° C. in a total atmosphere condition in an artificial weather apparatus.
Criteria for determining herbicidal effects (growth inhibition) and phytotoxicity.
4 ... 90% to 100% of the herbicidal effect, phytotoxicity.
3 ... 70% to 89% of the herbicidal effect, phytotoxicity.
2 ... 40% to 69% of the herbicidal effect, phytotoxicity.
1 ... 1% to 39% of the herbicidal effect, phytotoxicity.
Herbicidal effect of 0 ... 0%, phytotoxicity.

  As a result, among the compounds represented by the general formula (1) of the present invention, the compound No. I-1, I-2 and I-3 have four points in the above judgment criteria at an active ingredient concentration of 10 ppm relative to barnyard grass It showed the above weeding effect.

  The compound represented by the general formula (1) of the present invention or a salt thereof has an excellent effect as a herbicide.

Claims (6)

General formula (1)
{Wherein R ¹ and R ³ are each independently
(a1) hydrogen atom;
(a2) halogen atom;
(a3) cyano group;
(a4) nitro group;
(a5) (C ₁ -C ₆ ) alkyl group;
(a6) (C ₂ -C ₆ ) alkenyl group;
(a7) (C ₂ -C ₆ ) alkynyl group;
(a8) (C ₃ -C ₆ ) cycloalkyl group;
(a9) (C ₁ -C ₆ ) alkoxy group;
(a10) halo (C ₁ -C ₆ ) alkyl group;
(a11) halo (C ₂ -C ₆ ) alkenyl group;
(a12) halo (C ₂ -C ₆ ) alkynyl group;
(a13) halo (C ₃ -C ₈ ) cycloalkyl group;
(a14) halo (C ₁ -C ₆ ) alkoxy group
(a15) (C ₁ -C ₆ ) alkylthio group;
(a16) (C ₁ -C ₆ ) alkylsulfinyl group;
(a17) (C ₁ -C ₆ ) alkylsulfonyl group;
(a18) halo (C ₁ -C ₆ ) alkylthio group;
(a19) halo (C ₁ -C ₆ ) alkylsulfinyl group;
(a20) halo (C ₁ -C ₆ ) alkylsulfonyl group;
(a21) phenyl group;
(a22) phenyloxy group; or
(a23) Phenyl (C ₁ -C ₆ ) alkyl group is shown.
p and q each independently represent an integer of 1 to 5;
R ² is
(b1) hydrogen atom;
(b2) (C ₁ -C ₆ ) alkyl group;
(b3) (C ₁ -C ₆ ) alkylcarbonyl group;
(b4) (C ₁ -C ₆ ) alkoxycarbonyl group; or
(b5) R ⁸ R ⁹ N carbonyl group (wherein R ⁸ and R ⁹ are each independently a hydrogen atom; (C ₁ -C ₆ ) alkyl group; halo (C ₁ -C ₆ ) alkyl group; phenyl group Or a phenyl (C ₁ -C ₆ ) alkyl group is shown).
Ring A represents the following structure A1; A2; A3 or A4.
(In the formula, ● indicates a bonding position,
Each R ⁴ is independently
(d1) hydrogen atom;
(d2) (C ₁ -C ₆ ) alkyl group; or
(d3) represents a halo (C ₁ -C ₆ ) alkyl group,
r1 represents an integer of 1 to 3;
r2 represents an integer of 1 to 4; )}
Or a salt thereof. R ¹ and R ³ are each independently
(a1) hydrogen atom;
(a2) halogen atom;
(a5) (C ₁ -C ₆ ) alkyl group; or
(a10) halo (C ₁ -C ₆ ) alkyl group,
R ² is
(b1) hydrogen atom,
Ring A is A1
R ⁴ is
(d1) The compound or the salt thereof according to claim 1, which is a hydrogen atom. R ¹ is
(a2) a halogen atom,
R ³ is
(a1) hydrogen atom; or
(a10) The compound or the salt thereof according to claim 1 or 2, which is a halo (C ₁ -C ₆ ) alkyl group. A herbicide comprising the compound according to any one of claims 1 to 3 or a salt thereof as an active ingredient.   A method of using a herbicide, which comprises treating plants or soil with an effective amount of the herbicide according to claim 4.   Use of the compound according to any one of claims 1 to 3 or a salt thereof as a herbicide.