WO2012050183A1

WO2012050183A1 - Pyrimidine compound and pesticidal application thereof

Info

Publication number: WO2012050183A1
Application number: PCT/JP2011/073631
Authority: WO
Inventors: 吉彦野倉
Original assignee: 住友化学株式会社
Priority date: 2010-10-15
Filing date: 2011-10-14
Publication date: 2012-04-19
Also published as: JP2012102090A

Abstract

Provided is a novel pyrimidine compound having pest control activity, the compound being represented by formula (1) (where R¹ represents a C₁-C₃ linear hydrocarbon group or the like optionally having one or more halogen atoms, R² represents a C₁-C₃ linear hydrocarbon group or the like optionally having one or more halogen atoms, G¹ represents nitrogen or the like, R³ represents a C₁-C₃ linear hydrocarbon group or the like optionally having one or more halogen atoms, R⁴ represents a C₁-C₆ linear hydrocarbon group or the like optionally having one or more halogen atoms, R⁵ represents a C₁-C₃ alkyl group or the like optionally having one or more halogen atoms, A represents a single bond or the like, Cyc represents J1 or J2 or the like, and Z represents Z1 or Z2 or the like).

Description

Pyrimidine compounds and their use for pest control

The present invention relates to a pyrimidine compound and its use for pest control.

A compound having a pest control activity has been found and developed as an active ingredient of a pest control agent. Also, certain types of pyrimidine compounds are known (see, for example, Patent Documents 1 and 2).

International Publication No. 2006/050249 International Publication No. 2004/046120

An object of the present invention is to provide a novel compound having a controlling activity against pests.

As a result of studying to find a compound having a control activity against pests, the present inventor has found that a pyrimidine compound represented by the following formula (1) has a control effect on pests, leading to the present invention. It was.
That is, the present invention is as follows.
[1] Formula (1)

[Where,
R ¹ represents a C1-C3 chain hydrocarbon group optionally having one or more halogen, hydrogen, halogen or amino group,
R ² represents a C1-C3 chain hydrocarbon group optionally having one or more halogens, hydrogen, halogen, hydroxyl group, mercapto group or amino group,
G ¹ represents nitrogen or —CR ⁶ ═ (wherein R ⁶ represents a C1-C3 chain hydrocarbon group optionally having one or more halogen, hydrogen, halogen or amino group). ,
R ³ represents a C1-C3 chain hydrocarbon group optionally having one or more halogen, hydrogen, halogen, amino group, nitro group or cyano group,
R ⁴ represents a C1-C6 chain hydrocarbon group which may have one or more halogens, a C3-C8 cycloalkyl group which may have one or more halogens, one or more halogens. C1-C6 alkoxy group which may have, C1-C6 alkylthio group which may have one or more halogens, C1-C6 alkylsulfinyl group which may have one or more halogens, C1-C6 alkylsulfonyl group which may have one or more halogens, C1-C6 alkylamino group which may have one or more halogens, C2 which may have one or more halogens -C8 dialkylamino group, C2-C6 alkylcarbonylamino group optionally having one or more halogens, C2-C6 alkoxycarbonylamino optionally having one or more halogens A C2-C6 alkylcarbonyl group which may have one or more halogens, a C2-C6 alkoxycarbonyl group which may have one or more halogens, and one or more halogens. May have a C2-C6 alkylcarbamoyl group, a C2-C8 dialkylcarbamoyl group optionally having one or more halogens, and one or more atoms or groups selected from the following group α. A phenyl group, a phenoxy group optionally having one or more atoms or groups selected from the following group α, and one or more atoms or groups selected from the following group α: Represents a 6-membered aromatic heterocyclic group, hydrogen, halogen, hydroxyl group, mercapto group, amino group, nitro group, cyano group or formyl group,
R ⁵ represents a C1-C3 alkyl group which may have one or more halogens or hydrogen,
A represents a methylene group which may have one or more atoms or groups selected from the group consisting of a single bond, a C1-C3 alkyl group and halogen;
Cyc is the following formula J1 or J2

{In the formula, point a represents a bond with A,
R ⁷ and R ⁸ are the same or different and each represents a C1-C3 alkyl group or halogen which may have one or more halogens,
p represents any integer of 0 to 9 (provided that when p is an integer of 2 to 9, each R ⁷ may be different from each other);
q represents an integer of 0 to 7 (provided that when q is an integer of 2 to 7, each R ⁸ may be different from each other). } Represents a group represented by
Z is the following formula Z1 or Z2

{In the formula, point b represents a bond with the group represented by Cyc,
R ⁹ represents a C1-C6 chain hydrocarbon group optionally having one or more halogens, a C3-C8 cycloalkyl group optionally having one or more halogens, and one or more halogens. A C4-C8 (cycloalkyl) alkyl group which may have, a phenyl group which may have one or more atoms or groups selected from the following group α, a benzyl group or hydrogen;
L ¹ represents a single bond, oxygen, sulfur or —NR ¹¹ — (wherein R ¹¹ represents a C1-C6 chain hydrocarbon group which may have one or more halogens or hydrogen). ,
Q represents oxygen or sulfur,
R ¹⁰ represents a C1-C6 chain hydrocarbon group which may have one or more halogens, or hydrogen,
L ² represents a single bond or —NR ¹² — (wherein R ¹² represents a C1-C6 chain hydrocarbon group which may have one or more halogen atoms or hydrogen, and L ² represents In the case of a single bond, R ¹⁰ represents a C1-C6 chain hydrocarbon group which may have one or more halogens.
Group α: C1-C6 chain hydrocarbon group optionally having one or more halogens, C1-C6 alkoxy group optionally having one or more halogens, having one or more halogens C1-C6 alkylthio group which may have one, C1-C6 alkylsulfinyl group which may have one or more halogens, C1-C6 alkylsulfonyl group which may have one or more halogens, C1-C6 alkylamino group optionally having one or more halogens, C2-C8 dialkylamino group optionally having one or more halogens, halogen, hydroxyl group, mercapto group, amino group, cyano group and nitro group A group of groups. ]
The pyrimidine compound shown by these. (Hereinafter referred to as the present compound.)
[2] The pyrimidine compound according to [1], wherein R ¹ is hydrogen, R ² is hydrogen, and G ¹ is nitrogen.
[3] The pyrimidine compound according to [1] or [2], wherein R ⁵ is hydrogen.
[4] The pyrimidine compound according to any one of [1] to [3], wherein A is a single bond.
[5] The pyrimidine compound according to any one of [1] to [4], wherein Cyc is a group represented by J1.
[6] The pyrimidine compound according to any one of [1] to [4], wherein Cyc is a group represented by J2.
[7] R ³ is hydrogen and R ⁴ is a C1-C6 alkyl group which may have one or more halogens, a C1-C6 alkoxy group which may have one or more halogens, The pyrimidine compound according to any one of [1] to [6], which is a C1-C6 alkylthio group which may have one or more halogens or a halogen.
[8] The pyrimidine compound according to any one of [1] to [7], wherein Z is a group represented by Z1.
[9] Z is a group represented by Z1, R ⁹ is a branched C1-C6 alkyl group optionally having one or more halogens, L ¹ is oxygen or —NR ¹¹ —; The pyrimidine compound according to any one of [1] to [8], wherein R ¹¹ is a C1-C6 alkyl group which may have one or more halogens or hydrogen, and Q is oxygen.
[10] Formula (1-vii)

[Wherein, R ⁴ , R ⁹ , L ¹ and Q represent the same meaning as described above. ] The pyrimidine compound shown by this.
[11] R ⁴ is hydrogen, methyl group, ethyl group, methoxy group, fluorine, chlorine or bromine, R ⁹ is tert-butyl group or tert-pentyl group, and L ¹ is oxygen or —NR ¹¹ —. The pyrimidine compound according to [10], wherein R ¹¹ is hydrogen and Q is oxygen.
[12] R ¹ is a C1-C3 chain hydrocarbon group optionally having one or more halogens, hydrogen or halogen,
R ² is hydrogen or an amino group,
G ¹ is nitrogen or —CR ⁶ = (where R ⁶ is hydrogen);
R ³ is a C1-C3 chain hydrocarbon group or hydrogen optionally having one or more halogens,
R ⁴ is a C1-C6 chain hydrocarbon group optionally having one or more halogens, a C1-C6 alkoxy group optionally having one or more halogens, one selected from the group α A phenyl group optionally having the above atoms or groups, a 5-6 membered aromatic heterocyclic group optionally having one or more atoms or groups selected from the following group α, hydrogen, halogen, An amino group, a nitro group or a cyano group,
R ⁵ is a C1-C3 alkyl group optionally having one or more halogens or hydrogen,
A is a methylene group which may have one or more atoms or groups selected from the group consisting of a single bond, a C1-C3 alkyl group and halogen;
Cyc is J1 or J2 {p is 0 and q is 0. }, And
Z is Z1 or Z2 {R ⁹ is a C1-C6 chain hydrocarbon group optionally having one or more halogens; C3-C8 cycloalkyl group optionally having one or more halogens , A phenyl group or a benzyl group which may have one or more atoms or groups selected from group α, and L ¹ is a single bond, oxygen or —NR ¹¹ — (wherein R ¹¹ is A C1-C6 chain hydrocarbon group or hydrogen which may have one or more halogens), Q is oxygen or sulfur, and R ¹⁰ has one or more halogens. A C1-C6 chain hydrocarbon group, and L ² is a single bond},
The pyrimidine compound according to [1], wherein group α is a nitro group.
[13] R ¹ is a C1-C3 alkyl group optionally having one or more halogen, hydrogen or halogen,
R ² is hydrogen or an amino group,
G ¹ is nitrogen or —CR ⁶ = (where R ⁶ is hydrogen);
R ³ is a C1-C3 alkyl group or hydrogen;
R ⁴ is a C1-C6 alkyl group, a C1-C6 alkoxy group, a phenyl group, a 5-6-membered aromatic heterocyclic group, hydrogen, halogen, amino group, nitro group or cyano group,
R ⁵ is a C1-C3 alkyl group or hydrogen;
A is a single bond or a methylene group,
Cyc is J1 or J2 {p is 0 and q is 0. }, And
Z is Z1 or Z2 {R ⁹ is a C1-C6 chain hydrocarbon group optionally having one or more halogens, a C3-C8 cycloalkyl group, one or more atoms selected from the group α, or An optionally substituted phenyl group or benzyl group, L ¹ is a single bond, oxygen or —NR ¹¹ — (wherein R ¹¹ is a C1-C6 alkyl group or hydrogen); Q is oxygen or sulfur, R ¹⁰ is a C1-C6 alkyl group, and L ² is a single bond.
The pyrimidine compound according to [1], wherein group α is a nitro group.
[14] A pest control agent comprising the pyrimidine compound according to any one of [1] to [13] and an inert carrier.
[15] Use of the pyrimidine compound according to any one of [1] to [13] for controlling pests.
[16] A method for controlling pests comprising a step of applying an effective amount of the pyrimidine compound according to any one of [1] to [13] to a pest or a pest habitat.

Since the compound of the present invention has a pest control activity, it is useful as an active ingredient of a pest control agent.

In the compound of the present invention, “halogen” includes fluorine, chlorine, bromine and iodine. In the present invention, each halogen in a group having a plurality of halogens such as “C1-C3 chain hydrocarbon group optionally having one or more halogens” is the same halogen atom. Or different halogen atoms.
In the present specification, the number of carbons shown before each substituent means the number of carbons constituting the substituent. For example, the description of the part “C2-C6” represented by “C2-C6 alkoxycarbonyl group” Means that the number of carbon atoms constituting the entire alkoxycarbonyl group is in the range of 2-6.

In the compound of the present invention, the “chain hydrocarbon group” means a linear or branched group consisting of a carbon atom and a hydrogen atom, and a carbon-carbon double bond and / or triple bond can be appropriately selected. You may have. Examples thereof include a chain alkyl group, an alkenyl group, and an alkynyl group.
In the compounds of the present invention, examples of the “C1-C3 chain hydrocarbon group” include C1-C3 alkyl groups such as methyl group, ethyl group, propyl group and isopropyl group; C2-C3 alkenyl groups such as vinyl group and 2-propenyl group Groups; C2-C3 alkynyl groups such as ethynyl group and 2-propynyl group.
In the compound of the present invention, examples of the “C1-C3 alkyl group” include a methyl group, an ethyl group, a propyl group, and an isopropyl group.

Examples of the “C1-C3 chain hydrocarbon group optionally having one or more halogens” in the compound of the present invention include a methyl group, an ethyl group, a propyl group, an isopropyl group, a difluoromethyl group, a trifluoromethyl group. A dichloromethyl group, a trichloromethyl group, a 2,2,2-trifluoroethyl group, a 2,2,2-trichloroethyl group, a pentafluoroethyl group and a perfluoropropyl group. An optionally substituted C1-C3 alkyl group;
A C2-C3 alkenyl group optionally having one or more halogens such as a vinyl group, 2-propenyl group, 2,2-dichlorovinyl group and 3-chloro-2-propenyl group;
And C2-C3 alkynyl group which may have one or more halogens such as ethynyl group and 2-propynyl group.

In the compounds of the present invention, examples of the “C1-C6 chain hydrocarbon group” include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, isopentyl group. A C1-C6 alkyl group such as a group, 1-methylbutyl group, tert-pentyl group, neopentyl group, hexyl group and isohexyl group;
C2-C6 such as vinyl group, 2-propenyl group, 2-butenyl group, 3-butenyl group, 2-methyl-2-propenyl group, 3-methyl-2-butenyl group, 2-pentenyl group and 2-hexenyl group An alkenyl group;
Examples include C2-C6 alkynyl groups such as ethynyl group, 2-propynyl group, 2-butynyl group and 3-butynyl group.
In the compounds of the present invention, examples of the “C1-C6 alkyl group” include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, isopentyl group, 1 -Methylbutyl, tert-pentyl, neopentyl, hexyl and isohexyl groups. Examples of the “branched C1-C6 alkyl group” include isopropyl group, isobutyl group, sec-butyl group, tert-butyl group, isopentyl group, 1-methylbutyl group, tert-pentyl group, neopentyl group and isohexyl group. Groups.

In the compound of the present invention, examples of the “C1-C6 chain hydrocarbon group optionally having one or more halogen” include, for example, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec- Butyl, tert-butyl, pentyl, isopentyl, 1-methylbutyl, tert-pentyl, neopentyl, hexyl, isohexyl, difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl One or more halogens such as a group, 2,2,2-trifluoroethyl group, 2,2,2-trichloroethyl group, pentafluoroethyl group, perfluoropropyl group, perfluorobutyl group and perfluorohexyl group. An optionally substituted C1-C6 alkyl group;
Vinyl group, 2-propenyl group, 3-chloro-2-propenyl group, 2-chloro-2-propenyl group, 3,3-dichloro-2-propenyl group, 2-butenyl group, 3-butenyl group, 2-methyl A C2-C6 alkenyl group optionally having one or more halogens such as a 2-propenyl group, a 3-methyl-2-butenyl group, a 2-pentenyl group and a 2-hexenyl group;
Examples include ethynyl group, 2-propynyl group, 2-butynyl group, 3-butynyl group, 3-chloro-2-propynyl group and 3-bromo-2-propynyl group.

Examples of the “C3-C8 cycloalkyl group” in the compound of the present invention include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group.
Examples of the “C3-C8 cycloalkyl group optionally having one or more halogens” in the compounds of the present invention include a cyclopropyl group, a 2,2-difluorocyclopropyl group, a 2,2-dichlorocyclopropyl group, Examples include 2,2-dibromocyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group and cyclooctyl group.

In the compound of the present invention, examples of the “C1-C6 alkoxy group” include methoxy group, ethoxy group, propyloxy group, isopropyloxy group, butoxy group, isobutyloxy group, sec-butyloxy group, tert-butyloxy group, pentyloxy group and A hexyloxy group is mentioned.
Examples of the “C1-C6 alkoxy group optionally having one or more halogens” in the compounds of the present invention include methoxy group, trifluoromethoxy group, ethoxy group, 2,2,2-trifluoroethoxy group, propyl Examples thereof include an oxy group, isopropyloxy group, butoxy group, isobutyloxy group, sec-butyloxy group, tert-butyloxy group, pentyloxy group and hexyloxy group.

Examples of the “C1-C6 alkylthio group optionally having one or more halogens” in the compounds of the present invention include a methylthio group, a trifluoromethylthio group, an ethylthio group, a 2,2,2-trifluoroethylthio group, Examples include propylthio group, isopropylthio group, butylthio group, isobutylthio group, sec-butylthio group, tert-butylthio group, pentylthio group and hexylthio group.

Examples of the “C1-C6 alkylsulfinyl group optionally having one or more halogens” in the compounds of the present invention include a methylsulfinyl group, a trifluoromethylsulfinyl group, an ethylsulfinyl group, and 2,2,2-trifluoro. Examples thereof include ethylsulfinyl group, propylsulfinyl group, isopropylsulfinyl group, butylsulfinyl group, isobutylsulfinyl group, sec-butylsulfinyl group, tert-butylsulfinyl group, pentylsulfinyl group and hexylsulfinyl group.

In the compound of the present invention, examples of the “C1-C6 alkylsulfonyl group optionally having one or more halogens” include a methylsulfonyl group, a trifluoromethylsulfonyl group, and an ethylsulfonyl group.

In the compound of the present invention, examples of the “C1-C6 alkylamino group optionally having one or more halogen” include, for example, methylamino group, ethylamino group, 2,2,2-trifluoroethylamino group, propylamino group Group, isopropylamino group, butylamino group, pentylamino group and hexylamino group.
Examples of the “C2-C8 dialkylamino group optionally having one or more halogens” in the compounds of the present invention include a dimethylamino group, a diethylamino group, a bis (2,2,2-trifluoroethyl) amino group, And a dipropylamino group. Here, the dialkyl may be the same alkyl or different alkyl.

Examples of the “C2-C6 alkylcarbonylamino group optionally having one or more halogens” in the compounds of the present invention include an acetylamino group, a propionylamino group, a butyroxyamino group, a pentyloxyamino group, 2,2 , 2-trifluoroacetylamino group and 2,2,2-trichloroacetylamino group.

Examples of the “C2-C6 alkoxycarbonylamino group optionally having one or more halogens” in the compounds of the present invention include a methoxycarbonylamino group, an ethoxycarbonylamino group, a propoxycarbonylamino group, and a tert-butoxycarbonylamino group. And 2,2,2-trichloroethoxycarbonylamino group.

In the compound of the present invention, examples of the “C2-C6 alkylcarbonyl group optionally having one or more halogen” include acetyl group, propionyl group, butyroxy group, pentyloxy group, 2,2,2-trifluoroacetyl group And 2,2,2-trichloroacetyl group.
Examples of the “C2-C6 alkoxycarbonyl group optionally having one or more halogens” in the compounds of the present invention include a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, a tert-butoxycarbonyl group, and 2,2, A 2-trichloroethoxycarbonyl group may be mentioned.
Examples of the “C2-C6 alkylcarbamoyl group optionally having one or more halogens” in the compounds of the present invention include a methylcarbamoyl group, an ethylcarbamoyl group, and a 2,2,2-trifluoroethylcarbamoyl group. .

In the compound of the present invention, examples of the “C2-C8 dialkylcarbamoyl group optionally having one or more halogens” include a dimethylcarbamoyl group, a diethylcarbamoyl group, and a dipropylcarbamoyl group. Here, the dialkyl may be the same alkyl or different alkyl.

Examples of the “C1-C3 alkyl group optionally having one or more halogens” in the compounds of the present invention include a methyl group, an ethyl group, a propyl group, an isopropyl group, and a 2,2,2-trifluoroethyl group. Can be mentioned.
Examples of the “C1-C6 alkyl group optionally having one or more halogens” in the compounds of the present invention include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, tert-butyl, pentyl, isopentyl, 1-methylbutyl, tert-pentyl, neopentyl, hexyl, isohexyl, difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, 2 2,2-trifluoroethyl group, 2,2,2-trichloroethyl group, pentafluoroethyl group, perfluoropropyl group, perfluorobutyl group and perfluorohexyl group.

Examples of the “methylene group optionally having one or more atoms or groups selected from the group consisting of C1-C3 alkyl groups and halogen” in the compounds of the present invention include a methylene group, a (methyl) methylene group, (ethyl ) A methylene group, a difluoromethylene group and a dichloromethylene group.

In the compounds of the present invention, examples of the “phenyl group optionally having one or more atoms or groups selected from the group α” include a phenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, 2 -Aminophenyl group, 3-aminophenyl group, 4-aminophenyl group, 2-cyanophenyl group, 3-cyanophenyl group, 4-cyanophenyl group, 2-nitrophenyl group, 3-nitrophenyl group, 4-nitro Phenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 2- (trifluoromethyl) phenyl group, 3- (trifluoromethyl) phenyl group, 4- (trifluoromethyl) phenyl group 2-methoxyphenyl group, 3-methoxyphenyl group, 4-methoxyphenyl group, 4- (trifluoromethoxy) Eniru group, 4- (methylthio) phenyl group, 4- (methylsulfinyl) phenyl and 4- (methylsulfonyl) phenyl group.

In the compounds of the present invention, examples of the “phenoxy group optionally having one or more atoms or groups selected from group α” include, for example, phenoxy group, 2-chlorophenoxy group, 3-chlorophenoxy group, 4-chlorophenoxy group Group, 4-aminophenoxy group, 4-cyanophenoxy group, 4-nitrophenoxy group, 4-methylphenoxy group, 4-methoxyphenoxy group and 4- (trifluoromethyl) phenoxy group.

In the compound of the present invention, examples of the “5-6-membered aromatic heterocyclic group” include 2-pyrrolyl group, 2-furyl group, 3-furyl group, 2-thienyl group, 3-thienyl group, 5-pyrazolyl group, 4 -Pyrazolyl group, 2-pyridinyl group, 3-pyridinyl group, 4-pyridinyl group, pyrazinyl group, 1-pyrrolyl group and 1-pyrazolyl group.

In the compounds of the present invention, “a 5-6-membered aromatic heterocyclic group optionally having one or more atoms or groups selected from group α” includes, for example, 1-methyl-2-pyrrolyl group, 2-furyl Group, 3-furyl group, 5-bromo-2-furyl group, 5-nitro-2-furyl group, 2-methyl-3-furyl group, 2,5-dimethyl-3-furyl group, 2,4-dimethyl -3-furyl group, 2-thienyl group, 3-thienyl group, 5-methyl-2-thienyl group, 3-methyl-2-thienyl group, 1-methyl-3-trifluoromethyl-5-pyrazolyl group, 5 -Chloro-1,3-dimethyl-4-pyrazolyl group, 2-pyridinyl group, 3-pyridinyl group, 4-pyridinyl group, 2-methyl-3-pyridinyl group, 6-methyl-3-pyridinyl group, 2-chloro -3-pyridinyl group, 6-chloro- - pyridinyl group, a pyrazinyl group, and a 1-pyrrolyl group and 1-pyrazolyl group.

Examples of the “C4-C8 (cycloalkyl) alkyl group optionally having one or more halogens” in the compound of the present invention include (cyclopropyl) methyl group, (2,2-difluorocyclopropyl) methyl group, (2,2-dichlorocyclopropyl) methyl group, (2,2-dibromocyclopropyl) methyl group, (cyclobutyl) methyl group, (cyclopentyl) methyl group, (cyclohexyl) methyl group and (cycloheptyl) methyl group It is done.

Examples of the “C2-C6 alkylcarbonyl group optionally having one or more halogens” in the compounds of the present invention include an acetyl group, a propionyl group, a butanoyl group, a pentanoyl group, and a 2,2,2-trifluoroacetyl group. Is mentioned.

In the compound of the present invention, examples of the “C2-C6 alkoxycarbonyl group optionally having one or more halogens” include a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, and 2,2,2-trifluoroethoxycarbonyl. Group and tert-butoxycarbonyl group.

In the compounds of the present invention, examples of the “branched C1-C6 alkyl group optionally having one or more halogens” include, for example, isopropyl group, isobutyl group, sec-butyl group, tert-butyl group, isopentyl group, 1- Examples include methylbutyl group, 1,1-dimethylethyl group, tert-pentyl group, neopentyl group and isohexyl group.

Examples of the compound of the present invention include the following pyrimidine compounds.

A pyrimidine compound represented by formula (1), wherein R ¹ is a C1-C3 chain hydrocarbon group, hydrogen or halogen optionally having one or more halogens.
A pyrimidine compound represented by formula (1), wherein R ¹ is hydrogen or halogen.
A pyrimidine compound represented by formula (1), wherein R ¹ is hydrogen.

A pyrimidine compound represented by formula (1), wherein R ² is a C1-C3 chain hydrocarbon group, hydrogen, amino group or halogen optionally having one or more halogens.
A pyrimidine compound represented by formula (1), wherein R ² is hydrogen, an amino group or halogen.
A pyrimidine compound represented by formula (1), wherein R ² is hydrogen or an amino group.
A pyrimidine compound represented by formula (1), wherein R ² is hydrogen.

A pyrimidine compound represented by formula (1), wherein G ¹ is nitrogen.
A pyrimidine compound represented by formula (1), wherein G ¹ is -CR ⁶ =.
A pyrimidine compound represented by formula (1), wherein G ¹ is -CR ⁶ = and R ⁶ is hydrogen.

A pyrimidine compound represented by formula (1), wherein R ¹ is hydrogen, R ² is hydrogen or an amino group, G ¹ is nitrogen or —CR ⁶ ═, and R ⁶ is hydrogen.
A pyrimidine compound represented by formula (1), wherein R ¹ is hydrogen, R ² is hydrogen, G ¹ is nitrogen or —CR ⁶ ═, and R ⁶ is hydrogen.
A pyrimidine compound represented by formula (1), wherein R ¹ is hydrogen, R ² is hydrogen or an amino group, and G ¹ is nitrogen.
A pyrimidine compound represented by formula (1), wherein R ¹ is hydrogen, R ² is hydrogen, and G ¹ is nitrogen.
A pyrimidine compound represented by formula (1), wherein R ¹ is hydrogen, R ² is hydrogen, G ¹ is -CR ⁶ =, and R ⁶ is hydrogen.

A pyrimidine compound represented by formula (1), wherein R ³ is a C1-C3 chain hydrocarbon group which may have one or more halogens, or hydrogen.
A pyrimidine compound represented by formula (1), wherein R ³ is hydrogen.

In the formula (1), R ⁴ is a C1-C6 chain hydrocarbon group which may have one or more halogens, a C3-C8 cycloalkyl group which may have one or more halogens, 1 C1-C6 alkoxy group optionally having one or more halogens, C1-C6 alkylthio group optionally having one or more halogens, C1-C6 optionally having one or more halogens Alkylsulfinyl group, C1-C6 alkylsulfonyl group optionally having one or more halogens, C1-C6 alkylamino group optionally having one or more halogens, having one or more halogens C2-C8 dialkylamino group optionally having C1-C6 alkylcarbonylamino group optionally having one or more halogens, C2-C6 alcohol optionally having one or more halogens Cicarbonylamino group, C2-C6 alkylcarbonyl group optionally having one or more halogens, C2-C6 alkoxycarbonyl group optionally having one or more halogens, having one or more halogens C2-C6 alkylcarbamoyl group which may have one or more, C2-C8 dialkylcarbamoyl group which may have one or more halogen, hydrogen, halogen, hydroxyl group, mercapto group, amino group, nitro group, cyano group or formyl A pyrimidine compound as a group.
In the formula (1), R ⁴ may have a phenyl group which may have one or more atoms or groups selected from the group α or one or more atoms or groups selected from the group α. A pyrimidine compound which is a 5-6-membered aromatic heterocyclic group.
In the formula (1), R ⁴ may be a C1-C6 chain hydrocarbon group optionally having one or more halogens, a C1-C6 alkoxy group optionally having one or more halogens, hydrogen, A pyrimidine compound which is a halogen, a hydroxyl group, a mercapto group, an amino group, a nitro group or a cyano group.
In the formula (1), R ⁴ may be a C1-C6 alkyl group which may have one or more halogens, a C1-C6 alkoxy group which may have one or more halogens, a halogen, a hydroxyl group, a mercapto A pyrimidine compound which is a group, amino group, nitro group or cyano group.
A pyrimidine compound in which R ⁴ is a C1-C6 alkyl group optionally having one or more halogens, a C1-C6 alkoxy group optionally having one or more halogens, or a halogen in formula (1) .
A pyrimidine compound in which R ⁴ is a C1-C3 alkyl group optionally having one or more halogens, a C1-C3 alkoxy group optionally having one or more halogens, or a halogen in formula (1) .
A pyrimidine compound represented by formula (1), wherein R ⁴ is halogen, a C1-C3 alkyl group or a C1-C3 alkoxy group.
In the formula (1), R ⁴ is a methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, isopentyl group, 1-methylbutyl group, tert- Pentyl group, neopentyl group, hexyl group, isohexyl group, difluoromethyl group, trifluoromethyl group, dichloromethyl group, trichloromethyl group, 2,2,2-trifluoroethyl group, 2,2,2-trichloroethyl Group, pentafluoroethyl group, perfluoropropyl group, perfluorobutyl group, perfluorohexyl group, methoxy group, trifluoromethoxy group, ethoxy group, 2,2,2-trifluoroethoxy group, propyloxy group, isopropyloxy Group, butoxy group, isobutyloxy group, sec-butyloxy group tert- butyloxy group, pentyloxy group, hexyloxy group, hydrogen, fluorine, pyrimidine compound is chlorine or bromine.
A pyrimidine compound represented by formula (1), wherein R ⁴ is hydrogen, methyl group, ethyl group, methoxy group, fluorine, chlorine or bromine.
A pyrimidine compound represented by formula (1), wherein R ⁴ is chlorine, bromine, iodine, methyl group, ethyl group, methoxy group or ethoxy group.
A pyrimidine compound represented by formula (1), wherein R ⁴ is chlorine.
A pyrimidine compound represented by formula (1), wherein R ⁴ is bromine.
A pyrimidine compound represented by formula (1), wherein R ⁴ is a methyl group.
A pyrimidine compound represented by formula (1), wherein R ⁴ is a methoxy group.

In the formula (1), R ³ is hydrogen, and R ⁴ is a C1-C6 alkyl group which may have one or more halogens, and a C1-C6 alkoxy group which may have one or more halogens. A pyrimidine compound which is a group, an optionally substituted C1-C6 alkylthio group or halogen.
In the formula (1), R ³ is hydrogen, and R ⁴ is a C1-C6 alkyl group which may have one or more halogens, and a C1-C6 alkoxy group which may have one or more halogens. A pyrimidine compound which is a group or halogen.
In the formula (1), R ³ is hydrogen, and R ⁴ is a C1-C3 alkyl group which may have one or more halogens, and a C1-C3 alkoxy group which may have one or more halogens. A pyrimidine compound which is a group or halogen.
A pyrimidine compound represented by formula (1), wherein R ³ is hydrogen and R ⁴ is a C1-C3 alkyl group or a C1-C3 alkoxy group.
A pyrimidine compound represented by formula (1), wherein R ³ is hydrogen and R ⁴ is chlorine, bromine, iodine, a methyl group, an ethyl group, a methoxy group or an ethoxy group.
A pyrimidine compound represented by formula (1), wherein R ³ is hydrogen and R ⁴ is chlorine, bromine, methyl group or methoxy group.
A pyrimidine compound represented by formula (1), wherein R ³ is hydrogen and R ⁴ is chlorine.
A pyrimidine compound represented by formula (1), wherein R ³ is hydrogen and R ⁴ is bromine.
A pyrimidine compound represented by formula (1), wherein R ³ is hydrogen and R ⁴ is a methyl group.
A pyrimidine compound represented by formula (1), wherein R ³ is hydrogen and R ⁴ is a methoxy group.

A pyrimidine compound represented by formula (1), wherein R ⁵ is a C1-C3 alkyl group optionally having one or more halogens.
A pyrimidine compound represented by formula (1), wherein R ⁵ is hydrogen.

A pyrimidine compound represented by formula (1), wherein A is a single bond or a methylene group.
A pyrimidine compound represented by formula (1), wherein A is a single bond.

In the formula (1), Cyc is the following formula J1 or J2

R ⁷ and R ⁸ are the same or different and are a halogen or a C1-C3 alkyl group optionally having one or more halogens, p is any integer of 0 to 2, q A pyrimidine compound in which is an integer of 0 to 2.
A pyrimidine compound represented by formula (1), wherein Cyc is J1.
A pyrimidine compound represented by formula (1), wherein Cyc is J2.
A pyrimidine compound represented by formula (1), wherein Cyc is J1 or J2, and p and q are 0.
A pyrimidine compound represented by formula (1), wherein Cyc is J1 and p is 0.
A pyrimidine compound represented by formula (1), wherein Cyc is J2 and q is 0.

In the formula (1), Z is the following formula Z1 or Z2

R ⁹ is a C1-C6 chain hydrocarbon group which may have one or more halogens, L ¹ is a single bond, oxygen or —NR ¹¹ —, and R ¹¹ is hydrogen or 1 A C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, Q is oxygen, and R ¹⁰ is a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms A pyrimidine compound which is a group, L ² is a single bond or —NR ¹² —, and R ¹² is a C1-C6 chain hydrocarbon group or hydrogen optionally having one or more halogens.
In the formula (1), Z is Z1 or Z2, R ⁹ is a C1-C6 alkyl group which may have one or more halogens, L ¹ is oxygen or —NR ¹¹ —, R ¹¹ is one or more may have a halogen C1-C6 alkyl group or hydrogen, Q is oxygen, R ¹⁰ is 1 or more halogens have optionally may C1-C6 alkyl group in and, L ² is a single bond or -NR ¹² - is, pyrimidine compound wherein R ¹² is 1 or more may C1-C6 alkyl group or a hydrogen may have a halogen.
A pyrimidine compound represented by formula (1), wherein Z is Z1.
In the formula (1), Z is Z1, R ⁹ is a C1-C6 alkyl group which may have one or more halogens, L ¹ is oxygen or —NR ¹¹ —, and R ¹¹ is A pyrimidine compound which is a C1-C6 alkyl group optionally having one or more halogens or hydrogen, and Q is oxygen.
In the formula (1), Z is Z1, R ⁹ is a branched C1-C6 alkyl group optionally having one or more halogens, L ¹ is oxygen or —NR ¹¹ —, R ^A pyrimidine compound in which ¹¹ is hydrogen or a methyl group, and Q is oxygen.
In the formula (1), Z is Z1, R ⁹ is a tert-butyl group or a tert-pentyl group, L ¹ is oxygen or —NR ¹¹ —, R ¹¹ is hydrogen or a methyl group, Q A pyrimidine compound in which is oxygen.
A pyrimidine compound represented by formula (1), wherein Z is Z1, R ⁹ is a tert-butyl group or a tert-pentyl group, L ¹ is oxygen, and Q is oxygen.
A pyrimidine compound represented by formula (1), wherein Z is Z1, R ⁹ is a tert-butyl group, L ¹ is oxygen, and Q is oxygen.
A pyrimidine compound represented by formula (1), wherein Z is Z1, R ⁹ is a tert-pentyl group, L ¹ is oxygen, and Q is oxygen.
In the formula (1), Z is Z1, R ⁹ is a tert-butyl group or a tert-pentyl group, L ¹ is —NR ¹¹ —, R ¹¹ is hydrogen or a methyl group, and Q is oxygen A pyrimidine compound.

In formula (1), R ¹ is hydrogen, R ² is hydrogen, G ¹ is nitrogen, R ³ is hydrogen, and R ⁴ may have one or more halogens. A —C6 alkyl group, a C1-C6 alkoxy group optionally having one or more halogens, a C1-C6 alkylthio group optionally having one or more halogens or a halogen, and R ⁵ is hydrogen And A is a single bond, Cyc is J1 or J2, R ⁷ and R ⁸ are the same or different, and are a halogen or a C1-C3 alkyl group optionally having one or more halogens, A pyrimidine compound in which p is any integer from 0 to 2, q is any integer from 0 to 2, and Z is Z1.

In Formula (1), R ¹ is hydrogen, R ² is hydrogen, G ¹ is nitrogen, R ³ is hydrogen, and R ⁴ may have one or more halogens. A —C6 alkyl group, an optionally substituted C1-C6 alkoxy group or halogen, R ⁵ is hydrogen, A is a single bond, Cyc is J1, and Z is Z1 A pyrimidine compound.

In the formula (1), R ¹ is hydrogen, R ² is hydrogen, G ¹ is nitrogen, R ³ is hydrogen, R ⁴ is chlorine, bromine, methyl group or methoxy group, R A pyrimidine compound in which ⁵ is hydrogen, A is a single bond, Cyc is J1, and Z is Z1.

In Formula (1), R ¹ is hydrogen, R ² is hydrogen, G ¹ is nitrogen, R ³ is hydrogen, and R ⁴ may have one or more halogens. A —C6 alkyl group, an optionally substituted C1-C6 alkoxy group or halogen, R ⁵ is hydrogen, A is a single bond, Cyc is J1, and p is 0 Z is Z1, R ⁹ is a C1-C6 alkyl group optionally having one or more halogens, L ¹ is oxygen or —NR ¹¹ —, and R ¹¹ is one or more A pyrimidine compound which is a C1-C6 alkyl group optionally having a halogen or hydrogen and Q is oxygen.

In Formula (1), R ¹ is hydrogen, R ² is hydrogen, G ¹ is nitrogen, R ³ is hydrogen, and R ⁴ may have one or more halogens. A —C6 alkyl group, an optionally substituted C1-C6 alkoxy group or halogen, R ⁵ is hydrogen, A is a single bond, Cyc is J1, and p is 0 Z is Z1, R ⁹ is a branched C1-C6 alkyl group optionally having one or more halogens, L ¹ is oxygen or —NR ¹¹ —, and R ¹¹ is hydrogen Or a pyrimidine compound which is a methyl group and Q is oxygen.

In formula (1), R ¹ is hydrogen, R ² is hydrogen, G ¹ is nitrogen, R ³ is hydrogen, and R ⁴ may have one or more halogens. A —C6 alkyl group, an optionally substituted C1-C6 alkoxy group or halogen, R ⁵ is hydrogen, A is a single bond, Cyc is J1, and p is 0 Z is Z1, R ⁹ is a tert-butyl group or a tert-pentyl group, L ¹ is oxygen or —NR ¹¹ —, R ¹¹ is hydrogen or a methyl group, and Q is oxygen. A pyrimidine compound.

In the formula (1), R ¹ is hydrogen, R ² is hydrogen, G ¹ is nitrogen, R ³ is hydrogen, R ⁴ is chlorine, bromine, methyl group or methoxy group, R ⁵ is hydrogen, A is a single bond, Cyc is J1, p is 0, Z is Z1, R ⁹ is a tert-butyl group or a tert-pentyl group, and L ¹ is oxygen. Or a pyrimidine compound in which —NR ¹¹ —, R ¹¹ is hydrogen or a methyl group, and Q is oxygen.
Formula (1-vii)

[Wherein R ⁴ , R ⁹ , L ¹ and Q represent the same meaning as described above. ] The pyrimidine compound shown by this.
A pyrimidine compound represented by formula (1-vii), wherein R ⁴ is hydrogen, methyl group, ethyl group, methoxy group, fluorine, chlorine or bromine.
A pyrimidine compound represented by formula (1-vii), wherein R ⁴ is hydrogen.
A pyrimidine compound represented by formula (1-vii), wherein R ⁴ is a methyl group.
A pyrimidine compound represented by formula (1-vii), wherein R ⁴ is an ethyl group.
A pyrimidine compound represented by formula (1-vii), wherein R ⁴ is a methoxy group.
A pyrimidine compound represented by formula (1-vii), wherein R ⁴ is fluorine.
A pyrimidine compound represented by formula (1-vii), wherein R ⁴ is chlorine.
A pyrimidine compound represented by formula (1-vii), wherein R ⁴ is bromine.
A pyrimidine compound represented by formula (1-vii), wherein R ⁹ is a branched C1-C6 alkyl group optionally having one or more halogens.
A pyrimidine compound represented by formula (1-vii), wherein R ⁹ is a tert-butyl group or a tert-pentyl group.
A pyrimidine compound represented by formula (1-vii), wherein R ⁹ is a tert-butyl group.
A pyrimidine compound represented by formula (1-vii), wherein R ⁹ is a tert-pentyl group.
A pyrimidine compound represented by formula (1-vii), wherein L ¹ is oxygen or —NR ¹¹ —, and R ¹¹ is hydrogen.
A pyrimidine compound represented by formula (1-vii), wherein L ¹ is oxygen.
A pyrimidine compound represented by formula (1-vii), wherein L ¹ is -NR ^11- and R ¹¹ is hydrogen.
A pyrimidine compound represented by formula (1-vii), wherein Q is oxygen.
In formula (1-vii), R ⁴ is hydrogen, methyl group, ethyl group, methoxy group, fluorine, chlorine or bromine, and R ⁹ may have one or more halogens. A pyrimidine compound which is an alkyl group, L ¹ is oxygen, and Q is oxygen.
In the formula (1-vii), R ⁴ is hydrogen, methyl group, ethyl group, methoxy group, fluorine, chlorine or bromine, R ⁹ is tert-butyl group or tert-pentyl group, and L ¹ is oxygen or A pyrimidine compound in which —NR ¹¹ —, R ¹¹ is hydrogen, and Q is oxygen.
In the formula (1-vii), R ⁴ is hydrogen, methyl group, ethyl group, methoxy group, fluorine, chlorine or bromine, R ⁹ is tert-butyl group or tert-pentyl group, and L ¹ is oxygen. A pyrimidine compound in which Q is oxygen.
In the formula (1-vii), R ⁴ is hydrogen, methyl group, ethyl group, methoxy group, fluorine, chlorine or bromine, R ⁹ is tert-butyl group or tert-pentyl group, and L ¹ is —NR ^A pyrimidine compound in which ¹¹ is, R ¹¹ is hydrogen, and Q is oxygen.

Next, a method for producing the compound of the present invention will be described.

The compounds of the present invention include, for example, the following (Production Method A) to (Production Method D), (Production Method E-1) to (Production Method E-3) and (Production Method F-1) to (Production Method F- It can be manufactured according to 3).

(Production method A)
The compound of the present invention
Formula (2)

[Wherein R ¹ , R ² , R ³ , R ⁴ and G ¹ represent the same meaning as described above. ]
A compound represented by the following (hereinafter referred to as compound (2));
Formula (3)

[Wherein, Z, Cyc, A and R ⁵ represent the same meaning as described above. ]
It can manufacture by making the compound (henceforth a compound (3)) shown by reacting.
The reaction is performed in the presence or absence of a solvent. Examples of the solvent used for the reaction include water, ethers such as 1,4-dioxane, diethyl ether, tetrahydrofuran, tert-butyl methyl ether, halogenated compounds such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene and the like. Hydrocarbons such as hydrocarbon, toluene, benzene, xylene, nitriles such as acetonitrile, N, N-dimethylformamide (hereinafter referred to as DMF), N-methylpyrrolidone (hereinafter referred to as NMP), 1,3- Examples include aprotic polar solvents such as dimethyl-2-imidazolidinone and dimethyl sulfoxide, and mixtures thereof.
The amount of compound (3) used in the reaction is usually 1 to 2 moles relative to 1 mole of compound (2).
The reaction is usually performed in the presence of a base. Examples of the base used in the reaction include pyridine, picoline, 2,6-lutidine, 1,8-diazabicyclo [5.4.0] -7-undecene (hereinafter referred to as DBU), 1,5-diazabicyclo. Examples thereof include nitrogen-containing heterocyclic compounds such as [4.3.0] -5-nonene, tertiary amines such as triethylamine and N-ethyldiisopropylamine, and inorganic bases such as potassium carbonate and sodium hydride.
The amount of the base used in the reaction is usually 1 mol or more per 1 mol of the compound (2).
The reaction temperature of the reaction is usually in the range of −20 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the reaction mixture is poured into water and then extracted with an organic solvent, and the organic layer is concentrated; the reaction mixture is poured into water and the resulting solid is collected by filtration; or formed in the reaction mixture The compound of the present invention can be isolated by collecting the resulting solid by filtration. The isolated compound of the present invention can be further purified by recrystallization, chromatography or the like.

(Production method B)
The compound of the present invention
Formula (4)

[Wherein R ³ , R ⁴ , R ⁵ , A, Cyc and Z have the same meaning as described above. ]
A compound represented by formula (hereinafter referred to as compound (4)),
Formula (5)

[Wherein, R ¹ , R ² and G ¹ represent the same meaning as described above. ]
It can manufacture by making the compound (henceforth a compound (5)) shown by reacting.
The reaction is performed in the presence or absence of a solvent. Examples of the solvent used for the reaction include water, ethers such as 1,4-dioxane, diethyl ether, tetrahydrofuran, tert-butyl methyl ether, halogenated compounds such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene and the like. Examples include hydrocarbons, hydrocarbons such as toluene, benzene, xylene, nitriles such as acetonitrile, aprotic polar solvents such as DMF, NMP, 1,3-dimethyl-2-imidazolidinone, dimethyl sulfoxide, and mixtures thereof. .
The amount of compound (5) used in the reaction is usually 1 to 2 moles relative to 1 mole of compound (4).
The reaction is usually performed in the presence of a base. Examples of the base used in the reaction include nitrogen-containing heterocyclic compounds such as pyridine, picoline, 2,6-lutidine, DBU, 1,5-diazabicyclo [4.3.0] -5-nonene, triethylamine, N- Examples include tertiary amines such as ethyldiisopropylamine, and inorganic bases such as potassium carbonate and sodium hydride.
The amount of the base used in the reaction is usually 1 mol or more per 1 mol of the compound (4).
The reaction temperature of the reaction is usually in the range of −20 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the reaction mixture is poured into water and then extracted with an organic solvent, and the organic layer is concentrated; the reaction mixture is poured into water and the resulting solid is collected by filtration; or formed in the reaction mixture The compound of the present invention can be isolated by collecting the resulting solid by filtration. The isolated compound of the present invention can be further purified by recrystallization, chromatography or the like.

(Production method C)
The compound of the present invention
Formula (6)

[Wherein R ¹ , R ² , R ³ , R ⁴ and G ¹ represent the same meaning as described above. ]
A compound represented by formula (hereinafter referred to as compound (6)),
It can be produced by reacting compound (3).
The reaction is performed in the presence or absence of a solvent. Examples of the solvent used for the reaction include water, ethers such as 1,4-dioxane, diethyl ether, tetrahydrofuran, tert-butyl methyl ether, halogenated compounds such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene and the like. Examples include hydrocarbons, hydrocarbons such as toluene, benzene, xylene, nitriles such as acetonitrile, aprotic polar solvents such as DMF, NMP, 1,3-dimethyl-2-imidazolidinone, dimethyl sulfoxide, and mixtures thereof. .
The amount of compound (3) used in the reaction is usually 1 to 2 moles relative to 1 mole of compound (6).
The reaction is usually performed in the presence of a base. Examples of the base used in the reaction include nitrogen-containing heterocyclic compounds such as pyridine, picoline, 2,6-lutidine, DBU, 1,5-diazabicyclo [4.3.0] -5-nonene, triethylamine, N- Examples include tertiary amines such as ethyldiisopropylamine, and inorganic bases such as potassium carbonate and sodium hydride.
The amount of the base used in the reaction is usually 1 mol or more per 1 mol of the compound (6).
The reaction temperature of the reaction is usually in the range of −20 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the reaction mixture is poured into water and then extracted with an organic solvent, and the organic layer is concentrated; the reaction mixture is poured into water and the resulting solid is collected by filtration; or formed in the reaction mixture The compound of the present invention can be isolated by collecting the resulting solid by filtration. The isolated compound of the present invention can be further purified by recrystallization, chromatography or the like.

(Production method D)
Among the compounds of the present invention, the compound of the present invention represented by the following formula (1-i) wherein R ⁵ is a C1-C3 alkyl group optionally having one or more halogens (hereinafter referred to as the present compound (1- i).) can be produced, for example, by the following method.

[Wherein, R ¹ , R ² , R ³ , R ⁴ , G ¹ , A, Cyc and Z represent the same meaning as described above, and L represents chlorine, bromine, iodine, a paratoluenesulfonyloxy group or methanesulfonyloxy. Represents a leaving group such as a group, and R ^5-1 represents a C1-C3 alkyl group optionally having one or more halogens. ]
The reaction is performed in the presence or absence of a solvent. Examples of the solvent used for the reaction include water, ethers such as 1,4-dioxane, diethyl ether, tetrahydrofuran, tert-butyl methyl ether, halogenated compounds such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene and the like. Examples include hydrocarbons, hydrocarbons such as toluene, benzene, xylene, nitriles such as acetonitrile, aprotic polar solvents such as DMF, NMP, 1,3-dimethyl-2-imidazolidinone, dimethyl sulfoxide, and mixtures thereof. .
The amount of the compound represented by the formula (8) (hereinafter referred to as the compound (8)) used in the reaction is the amount of the compound of the present invention represented by the formula (1-ii) (hereinafter referred to as the present compound (1- ii)) The ratio is usually 1 to 2 moles per mole.
The reaction is usually performed in the presence of a base. Examples of the base used in the reaction include sodium hydride, potassium tert-butoxide and the like.
The amount of the base used in the reaction is usually 1 mol or more per 1 mol of the compound (1-ii) of the present invention.
The reaction temperature of the reaction is usually in the range of −20 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the reaction mixture is poured into water and then extracted with an organic solvent, and the organic layer is concentrated; the reaction mixture is poured into water and the resulting solid is collected by filtration; or formed in the reaction mixture The present compound (1-i) can be isolated by collecting the obtained solid by filtration. The isolated compound (1-i) of the present invention can be further purified by recrystallization, chromatography or the like.

(Production method E-1)
Among the compounds of the present invention, the compound of the present invention represented by the following formula (1-iii-1) (hereinafter referred to as the present compound (1-iii-1)) can be produced, for example, by the following method. .

[Wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁷ , R ⁹ , L ¹ , G ¹ , A, Q and p represent the same meaning as described above, and X represents halogen] . ]
The compound (1-iii-1) of the present invention includes a compound represented by the formula (9) (hereinafter referred to as the compound (9)) or a salt thereof (for example, hydrochloride) and the formula (10). Can be produced by reacting the compound represented by formula (hereinafter referred to as compound (10)) or the compound represented by formula (11) (hereinafter referred to as compound (11)).
The reaction is performed in the presence or absence of a solvent. Examples of the solvent used in the reaction include ethers such as 1,4-dioxane, diethyl ether, tetrahydrofuran and tert-butyl methyl ether, and halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane and chlorobenzene. Hydrocarbons such as toluene, benzene, xylene, nitriles such as acetonitrile, aprotic polar solvents such as DMF, NMP, 1,3-dimethyl-2-imidazolidinone, dimethyl sulfoxide, and mixtures thereof.
The amount of compound (10) or compound (11) used in the reaction is usually 1 to 2 moles per 1 mole of compound (9).
The reaction is usually performed in the presence or absence of a base. Examples of the base used in the reaction include nitrogen-containing heterocyclic compounds such as pyridine, picoline, 2,6-lutidine, DBU, 1,5-diazabicyclo [4.3.0] -5-nonene, triethylamine, N- Examples include tertiary amines such as ethyldiisopropylamine, and inorganic bases such as potassium carbonate and sodium hydride.
The amount of the base used in the reaction is usually 1 mol or more per 1 mol of the compound (9).
The reaction temperature of the reaction is usually in the range of −20 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the reaction mixture is poured into water and then extracted with an organic solvent, and the organic layer is concentrated; the reaction mixture is poured into water and the resulting solid is collected by filtration; or formed in the reaction mixture The present compound (1-iii-1) can be isolated by collecting the obtained solid by filtration. The isolated compound (1-iii-1) of the present invention can be further purified by recrystallization, chromatography or the like.

(Production method E-2)
Among the compounds of the present invention, the compound of the present invention represented by the following formula (1-iii-2) (hereinafter referred to as the present compound (1-iii-2)) can be produced, for example, by the following method. .

[Wherein, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁷ , R ⁹ , G ¹ , A, Q and p represent the same meaning as described above. ]
The compound (1-iii-2) of the present invention includes compound (9) or a salt thereof (for example, hydrochloride) and a compound represented by formula (12) (hereinafter referred to as compound (12)). Can be made to react.
The reaction is performed in the presence or absence of a solvent. Examples of the solvent used in the reaction include ethers such as 1,4-dioxane, diethyl ether, tetrahydrofuran and tert-butyl methyl ether, and halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane and chlorobenzene. Hydrocarbons such as toluene, benzene, xylene, nitriles such as acetonitrile, aprotic polar solvents such as DMF, NMP, 1,3-dimethyl-2-imidazolidinone, dimethyl sulfoxide, and mixtures thereof.
The amount of the compound (12) used in the reaction is usually 1 to 2 moles relative to 1 mole of the compound (9).
The reaction is usually performed in the presence or absence of a base. Examples of the base used in the reaction include nitrogen-containing heterocyclic compounds such as pyridine, picoline, 2,6-lutidine, DBU, 1,5-diazabicyclo [4.3.0] -5-nonene, triethylamine, N- Examples include tertiary amines such as ethyldiisopropylamine, and inorganic bases such as potassium carbonate and sodium hydride.
The amount of the base used in the reaction is usually 1 mol or more per 1 mol of the compound (9).
The reaction temperature of the reaction is usually in the range of −20 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the reaction mixture is poured into water and then extracted with an organic solvent, and the organic layer is concentrated; the reaction mixture is poured into water and the resulting solid is collected by filtration; or formed in the reaction mixture The present compound (1-iii-2) can be isolated by collecting the obtained solid by filtration. The isolated compound (1-iii-2) of the present invention can be further purified by recrystallization, chromatography or the like.

(Production Method E-3)
Among the compounds of the present invention, the compound of the present invention represented by the following formula (1-iv) (hereinafter referred to as the present compound (1-iv)) can be produced, for example, by the following method.

[Wherein, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁷ , R ¹⁰ , L ² , G ¹ , A, and p represent the same meaning as described above, and Y represents halogen. ]
The compound (1-iv) of the present invention includes the compound (9) or a salt thereof (for example, hydrochloride) and a compound represented by the formula (14) (hereinafter referred to as the compound (14)) or the formula It can be produced by reacting the compound represented by (15) (hereinafter referred to as compound (15)).
The reaction is performed in the presence or absence of a solvent. Examples of the solvent used in the reaction include ethers such as 1,4-dioxane, diethyl ether, tetrahydrofuran and tert-butyl methyl ether, and halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane and chlorobenzene. Hydrocarbons such as toluene, benzene, xylene, nitriles such as acetonitrile, aprotic polar solvents such as DMF, NMP, 1,3-dimethyl-2-imidazolidinone, dimethyl sulfoxide, and mixtures thereof.
The amount of compound (14) or compound (15) used in the reaction is usually 1 to 2 moles relative to 1 mole of compound (9).
The reaction is usually performed in the presence of a base. Examples of the base used in the reaction include nitrogen-containing heterocyclic compounds such as pyridine, picoline, 2,6-lutidine, DBU, 1,5-diazabicyclo [4.3.0] -5-nonene, triethylamine, N- Examples include tertiary amines such as ethyldiisopropylamine, and inorganic bases such as potassium carbonate and sodium hydride.
The amount of the base used in the reaction is usually 1 mol or more per 1 mol of the compound (9).
The reaction temperature of the reaction is usually in the range of −20 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the reaction mixture is poured into water and then extracted with an organic solvent, and the organic layer is concentrated; the reaction mixture is poured into water and the resulting solid is collected by filtration; or formed in the reaction mixture The present compound (1-iv) can be isolated by collecting the obtained solid by filtration. The isolated compound (1-iv) of the present invention can be further purified by recrystallization, chromatography or the like.

(Production Method F-1)
Among the compounds of the present invention, the compound of the present invention represented by the following formula (1-v-1) (hereinafter referred to as the present compound (1-v-1)) can be produced, for example, by the following method. .

[Wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁸ , R ⁹ , L ¹ , G ¹ , A, Q, X and q represent the same meaning as described above. ]
The compound (1-v-1) of the present invention includes a compound represented by the formula (16) (hereinafter referred to as the compound (16)) or a salt thereof (for example, hydrochloride) and the compound (10). Or it can manufacture by making a compound (11) react.
The reaction is performed in the presence or absence of a solvent. Examples of the solvent used in the reaction include ethers such as 1,4-dioxane, diethyl ether, tetrahydrofuran and tert-butyl methyl ether, and halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane and chlorobenzene. Hydrocarbons such as toluene, benzene, xylene, nitriles such as acetonitrile, aprotic polar solvents such as DMF, NMP, 1,3-dimethyl-2-imidazolidinone, dimethyl sulfoxide, and mixtures thereof.
The amount of compound (10) or compound (11) used in the reaction is usually 1 to 2 moles per 1 mole of compound (16).
The reaction is usually performed in the presence or absence of a base. Examples of the base used in the reaction include nitrogen-containing heterocyclic compounds such as pyridine, picoline, 2,6-lutidine, DBU, 1,5-diazabicyclo [4.3.0] -5-nonene, triethylamine, N- Examples include tertiary amines such as ethyldiisopropylamine, and inorganic bases such as potassium carbonate and sodium hydride.
The amount of the base used in the reaction is usually 1 mol or more per 1 mol of the compound (16).
The reaction temperature of the reaction is usually in the range of −20 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the reaction mixture is poured into water and then extracted with an organic solvent, and the organic layer is concentrated; the reaction mixture is poured into water and the resulting solid is collected by filtration; or formed in the reaction mixture The present compound (1-v-1) can be isolated by collecting the obtained solid by filtration. The isolated compound (1-v-1) of the present invention can be further purified by recrystallization, chromatography or the like.

(Production Method F-2)
Among the compounds of the present invention, the compound of the present invention represented by the following formula (1-v-2) (hereinafter referred to as the present compound (1-v-2)) can be produced, for example, by the following method. .

[Wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁸ , R ⁹ , G ¹ , A, Q and q represent the same meaning as described above. ]
The compound (1-v-2) of the present invention can be produced by reacting compound (16) or a salt thereof (for example, hydrochloride) with compound (12).
The reaction is performed in the presence or absence of a solvent. Examples of the solvent used in the reaction include ethers such as 1,4-dioxane, diethyl ether, tetrahydrofuran and tert-butyl methyl ether, and halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane and chlorobenzene. Hydrocarbons such as toluene, benzene, xylene, nitriles such as acetonitrile, aprotic polar solvents such as DMF, NMP, 1,3-dimethyl-2-imidazolidinone, dimethyl sulfoxide, and mixtures thereof.
The amount of the compound (12) used in the reaction is usually 1 to 2 moles relative to 1 mole of the compound (16).
The reaction is usually performed in the presence or absence of a base. Examples of the base used in the reaction include nitrogen-containing heterocyclic compounds such as pyridine, picoline, 2,6-lutidine, DBU, 1,5-diazabicyclo [4.3.0] -5-nonene, triethylamine, N- Examples include tertiary amines such as ethyldiisopropylamine, and inorganic bases such as potassium carbonate and sodium hydride.
The amount of the base used in the reaction is usually 1 mol or more per 1 mol of the compound (16).
The reaction temperature of the reaction is usually in the range of −20 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the reaction mixture is poured into water and then extracted with an organic solvent, and the organic layer is concentrated; the reaction mixture is poured into water and the resulting solid is collected by filtration; or formed in the reaction mixture The present compound (1-v-2) can be isolated by collecting the obtained solid by filtration. The isolated compound (1-v-2) of the present invention can be further purified by recrystallization, chromatography or the like.

(Production Method F-3)
Among the compounds of the present invention, the compound of the present invention represented by the following formula (1-vi) (hereinafter referred to as the present compound (1-vi)) can be produced, for example, by the following method.
[Wherein, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁸ , R ¹⁰ , L ² , G ¹ , A, Y, and q represent the same meaning as described above. ]
The compound (1-vi) of the present invention can be produced by reacting compound (16) or a salt thereof (for example, hydrochloride) with compound (14) or compound (15).
The reaction is performed in the presence or absence of a solvent. Examples of the solvent used in the reaction include ethers such as 1,4-dioxane, diethyl ether, tetrahydrofuran and tert-butyl methyl ether, and halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane and chlorobenzene. Hydrocarbons such as toluene, benzene, xylene, nitriles such as acetonitrile, aprotic polar solvents such as DMF, NMP, 1,3-dimethyl-2-imidazolidinone, dimethyl sulfoxide, and mixtures thereof.
The amount of compound (14) or compound (15) used in the reaction is usually 1 to 2 moles per 1 mole of compound (16).
The reaction is usually performed in the presence of a base. Examples of the base used in the reaction include nitrogen-containing heterocyclic compounds such as pyridine, picoline, 2,6-lutidine, DBU, 1,5-diazabicyclo [4.3.0] -5-nonene, triethylamine, N- Examples include tertiary amines such as ethyldiisopropylamine, and inorganic bases such as potassium carbonate and sodium hydride.
The amount of the base used in the reaction is usually 1 mol or more per 1 mol of the compound (16).
The reaction temperature of the reaction is usually in the range of −20 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the reaction mixture is poured into water and then extracted with an organic solvent, and the organic layer is concentrated; the reaction mixture is poured into water and the resulting solid is collected by filtration; or formed in the reaction mixture The present compound (1-vi) can be isolated by collecting the obtained solid by filtration. The isolated compound (1-vi) of the present invention can be further purified by recrystallization, chromatography or the like.

Next, a method for producing an intermediate for producing the compound of the present invention will be described.

(Reference production method 1)
Compound (2) is
Formula (17)

[Wherein R ³ and R ⁴ represent the same meaning as described above. ]
A compound represented by formula (hereinafter referred to as compound (17)),
It can be produced by reacting with compound (5).
The reaction is performed in the presence or absence of a solvent. Examples of the solvent used for the reaction include water, ethers such as 1,4-dioxane, diethyl ether, tetrahydrofuran, tert-butyl methyl ether, halogenated compounds such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene and the like. Examples include hydrocarbons, hydrocarbons such as toluene, benzene, xylene, nitriles such as acetonitrile, aprotic polar solvents such as DMF, NMP, 1,3-dimethyl-2-imidazolidinone, dimethyl sulfoxide, and mixtures thereof. .
The amount of compound (5) used in the reaction is usually 1 to 2 moles relative to 1 mole of compound (17).
The reaction is usually performed in the presence of a base. Examples of the base used in the reaction include nitrogen-containing heterocyclic compounds such as pyridine, picoline, 2,6-lutidine, DBU, 1,5-diazabicyclo [4.3.0] -5-nonene, triethylamine, N- Examples include tertiary amines such as ethyldiisopropylamine, and inorganic bases such as potassium carbonate and sodium hydride.
The amount of the base used in the reaction is usually 1 mol or more per 1 mol of the compound (17).
The reaction temperature of the reaction is usually in the range of −20 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the reaction mixture is poured into water and then extracted with an organic solvent, and the organic layer is concentrated; the reaction mixture is poured into water and the resulting solid is collected by filtration; or formed in the reaction mixture. The collected solid can be collected by filtration to isolate compound (2). The isolated compound (2) can be further purified by recrystallization, chromatography or the like.

(Reference production method 2)
Of the compounds (2)
Formula (2-i)

[Wherein R ³ and R ⁴ represent the same meaning as described above, and R ^1-1 represents a C1-C3 chain hydrocarbon group which may have one or more halogens or hydrogen. ]
(Hereinafter referred to as compound (2-i))
Formula (18)

[Wherein R ³ and R ⁴ represent the same meaning as described above. ]
A compound represented by formula (hereinafter referred to as compound (18)),
Formula (19)

[Wherein R ¹³ represents a C1-C6 alkyl group which may have one or more halogens, and R ^1-1 represents the same meaning as described above. ]
It can manufacture by making the compound shown below (it is hereafter described as a compound (19)) react.
The reaction is performed in the presence or absence of a solvent. Examples of the solvent used in the reaction include water; ethers such as 1,4-dioxane, diethyl ether, tetrahydrofuran, and tert-butyl methyl ether; halogenation such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, and chlorobenzene. Hydrocarbons such as toluene, benzene, xylene; nitriles such as acetonitrile; aprotic polar compounds such as DMF, NMP, 1,3-dimethyl-2-imidazolidinone, dimethyl sulfoxide; and mixtures thereof It is done.
The amount of the compound (19) used in the reaction is usually 1 to 2 mol with respect to 1 mol of the compound (18).
The reaction temperature of the reaction is usually in the range of −20 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (2-i) can be isolated by pouring the reaction mixture into water and extracting the mixture with an organic solvent, and concentrating the organic layer. The isolated compound (2-i) can be further purified by chromatography, distillation or the like.

(Reference production method 3)
Compound (18) can be produced by reacting compound (17) with hydrazine.
The reaction is performed in the presence or absence of a solvent. Examples of the solvent used in the reaction include water; ethers such as 1,4-dioxane, diethyl ether, tetrahydrofuran, and tert-butyl methyl ether; halogenation such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, and chlorobenzene. Hydrocarbons such as toluene, benzene, xylene; nitriles such as acetonitrile; aprotic polar compounds such as DMF, NMP, 1,3-dimethyl-2-imidazolidinone, dimethyl sulfoxide; and mixtures thereof It is done.
Examples of hydrazine used in the reaction include hydrazine and hydrazine hydrate.
The amount of hydrazine used in the reaction is usually 1 to 10 mol per 1 mol of compound (17).
The reaction is usually performed in the presence of a base. Examples of the base used in the reaction include nitrogen-containing heterocyclic compounds such as pyridine, picoline, 2,6-lutidine, DBU, 1,5-diazabicyclo [4.3.0] -5-nonene; triethylamine, N- Tertiary amines such as ethyldiisopropylamine; and inorganic bases such as potassium carbonate and sodium hydride.
The amount of the base used in the reaction is usually 1 mol or more per 1 mol of the compound (17).
The reaction temperature of the reaction is usually in the range of 0 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the reaction mixture is poured into water and then extracted with an organic solvent, and the organic layer is concentrated; the reaction mixture is poured into water and the resulting solid is collected by filtration; or formed in the reaction mixture Compound (18) can be isolated by collecting the resulting solid by filtration. The isolated compound (18) can be further purified by recrystallization, chromatography or the like.

(Reference production method 4)
Compound (4) can be produced by reacting compound (17) with compound (3).
The reaction is performed in the presence or absence of a solvent. Examples of the solvent used for the reaction include water, ethers such as 1,4-dioxane, diethyl ether, tetrahydrofuran, tert-butyl methyl ether, halogenated compounds such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene and the like. Examples include hydrocarbons, hydrocarbons such as toluene, benzene, xylene, nitriles such as acetonitrile, aprotic polar solvents such as DMF, NMP, 1,3-dimethyl-2-imidazolidinone, dimethyl sulfoxide, and mixtures thereof. .
The amount of compound (3) used in the reaction is usually 1 to 2 moles relative to 1 mole of compound (17).
The reaction is usually performed in the presence of a base. Examples of the base used in the reaction include nitrogen-containing heterocyclic compounds such as pyridine, picoline, 2,6-lutidine, DBU, 1,5-diazabicyclo [4.3.0] -5-nonene, triethylamine, N- Examples include tertiary amines such as ethyldiisopropylamine, and inorganic bases such as potassium carbonate and sodium hydride. The amount of the base used in the reaction is usually 1 mol or more per 1 mol of the compound (17).
The reaction temperature of the reaction is usually in the range of 0 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (4) can be isolated by pouring the reaction mixture into water and extracting the mixture with an organic solvent. The isolated compound (4) can be further purified by chromatography or the like.

(Reference production method 5)
Compound (6) can be produced by reacting compound (17) with compound (5).
The reaction is performed in the presence or absence of a solvent. Examples of the solvent used for the reaction include water, ethers such as 1,4-dioxane, diethyl ether, tetrahydrofuran, tert-butyl methyl ether, halogenated compounds such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene and the like. Examples include hydrocarbons, hydrocarbons such as toluene, benzene, xylene, nitriles such as acetonitrile, aprotic polar solvents such as DMF, NMP, 1,3-dimethyl-2-imidazolidinone, dimethyl sulfoxide, and mixtures thereof. .
The amount of compound (5) used in the reaction is usually 2 to 3 moles relative to 1 mole of compound (17).
The reaction is usually performed in the presence of a base. Examples of the base used in the reaction include nitrogen-containing heterocyclic compounds such as pyridine, picoline, 2,6-lutidine, DBU, 1,5-diazabicyclo [4.3.0] -5-nonene, triethylamine, N- Examples include tertiary amines such as ethyldiisopropylamine, and inorganic bases such as potassium carbonate and sodium hydride. The amount of the base used for the reaction is usually 2 mol or more per 1 mol of the compound (17).
The reaction temperature of the reaction is usually in the range of 0 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the reaction mixture is poured into water and then extracted with an organic solvent, and the organic layer is concentrated; the reaction mixture is poured into water and the resulting solid is collected by filtration; or formed in the reaction mixture The collected solid can be collected by filtration to isolate compound (6). The isolated compound (6) can be further purified by recrystallization, chromatography or the like.

Specific examples of the compound of the present invention are shown below.

A compound represented by formula (A).

In the formula, R ¹ , R ² , R ³ and R ⁵ represent hydrogen, G ¹ represents nitrogen, and Z, Cyc and A represent the combinations described in Table 1.

A compound represented by formula (B).

A compound represented by formula (C).

A compound represented by formula (D).

A compound represented by formula (E).

A compound represented by formula (F).

A compound represented by formula (G).

A compound represented by formula (H).

A compound represented by formula (I).

A compound represented by formula (J).

Examples of pests for which the compounds of the present invention are effective include harmful arthropods and nematodes such as harmful insects and harmful mites. Specific examples of such pests include the following.

Hemiptera: small brown planthopper (Laodelphax striatellus), brown planthopper (Nilaparvata lugens), planthoppers such as Sejirounka (Sogatella furcifera), green rice leafhopper (Nephotettix cincticeps), Taiwan green rice leafhopper (Nephotettix virescens), tea Roh green leafhopper (Empoasca onukii) such as Leafhoppers, cotton aphids (Aphis gossypii), peach aphids (Myzus persicae), radish aphids (Brevicoryne brassicae), aphid spiraecola, tulip beetle aphids Macrosiphum euphorbiae, potato beetle aphids (Aulacorthum solani), wheat beetle aphids (Rhopalosiphum aphids), citrus aphids (Tomoptera citricidus), peach beetles Stink bugs such as stink bugs (Riptortus clavetus), spider helicopter bugs (Leptocorisa chinensis), thornbill bugs (Eysarcoris parvus), winged bugs (Halyomorpha mista) odes vaporariorum), sweetpotato whitefly (Bemisia tabaci), mandarin orange whitefly (Dialeurodes citri), whiteflies such as mandarin orange spiny whitefly (Aleurocanthus spiniferus), Acamar scale insects (Aonidiella aurantii), Sanho zero scale insects (Comstockaspis perniciosa), citrus snow scale (Unaspis citri), Ruby Roe beetle (Ceroplastes rubens), Iceria scale insect (Icerya purchasi), Fujico scale insect (Pranococcus kraunhiae), Swan scale scale (Pseudococcus longi) spinis), scale insects such as Pseudaulaca spis pentagona, army beetles, bed bugs such as bed bugs (Cimex lectularius), and whales.

Lepidoptera: rice stem borer (Chilo suppressalis), Sankameiga (Tryporyza incertulas), leaf roller (Cnaphalocrocis medinalis), Watanomeiga (Notarcha derogata), Indian meal moth (Plodia interpunctella), the European corn borer (Ostrinia furnacalis), high Madara Roh moth (Hellula undalis), Japanese medusa such as Shibatatsuga (Pediasia teterrellus), Lotus moth (Spodoptera litura), Spodoptera exigua, Ayuyoto (Pseudaletia separata) Amestra brassicae, Agrotis ipsilon, Tamanaginuwaba (Prusia nigrisigna), Trichopulsia, Heliotis, Helicoberpas, etc. (Leguminivora glycinivolora), Azusa yamashiga (Matsumuraeses azukivorora), apple wolfberry (Adoxophyes orora fasciata), chanokokumon hamokihamomon (Adohomochamaki). ), Leafhoppers such as Archipes fuscocuppreanus, Cydonia pomonella, etc. Spiders such as leaf moths, Limantria, Euprocutis, etc., Suga such as Plutella xylostella, Pterinophora gossypiella, Phythromea operphylla such as Phythoreaea operculella Hitrigues such as ia cunea, and Hirokosukoga such as iga (Tinea translucens) and koiga (Tineola bisselliella).

Thrips of the order Thrips thrips, Sriptotrips dorsalis

Diptera: Culex (Culex pipiens pallens), Culex (Culex tritaeniorhynchus), Culex such as Culex quinquefasciatus (Culex quinquefasciatus), Aedes aegypti (Aedes aegypti), Aedes albopictus (Aedes albopictus) Aedes genus such as Anopheles sinensis (Anopheles sinensis), etc. Genus Anopheles, chironomid, housefly (Musca domestica), housefly (Muscina stabulans), etc. Moguribae (Agromyza oryzae), rice Hime leafminer (Hydrellia griseola), tomato leafminer, (Liriomyza sativae), legume leafminer (Liriomyza trifolii), leafminer such as the pea (Chromatomyia horticola), chloropidae such as Inekimoguribae (Chlorops oryzae), melon fly (Dacus cucurbitae), fruit flies such as Ceratitis capitata, fruit flies such as Drosophila, fleas such as Megaselia spiracularis, Clogmial etc. It flies such, blackfly acids, Abu acids, and stable flies such as gadfly (Tabanus trigonus).

Coleoptera pests: Western Corn Rootworm (Diabrotica virgifera virgifera), corn rootworm such as southern corn rootworm (Diabrotica undecimpunctata howardi), cupreous chafer (Anomala cuprea), rufocuprea (Anomala rufocuprea), chafers such as Japanese beetle (Popillia japonica) , Weevil (Sitophilus zeamais), Rice weevil (Lissorhoptrus oryzophilus), Azuki beetle (Callosobruchuys chiensis), Echonocnemus squatium (Echinocnemus squat) onomus grandis), weevils such as grass reed weevil (Sphenophorus venatus), Chai Loco Meno mealworm (Tenebrio molitor), mealworm such as red flour beetle (Tribolium castaneum),
Inedorooimushi (Oulema oryzae), cucurbit leaf beetle (Aulacophora femoralis), Kisujinomihamushi (Phyllotreta striolata), beetles such as Colorado potato beetle (Leptinotarsa decemlineata), varied carpet beetle (Anthrenus verbasci), carpet beetle such as Hara Giro beetle (Dermestes maculates), cigarette beetle (Lasiderma serricorne) and the like, Epilachna vigintioctopuncta and other epilacunas, Lyctus brunneus and pine beetle (Pompicus) erda), bark beetles, leopard caterpillars, longhorn beetles (Anoprophora malasiaca), longhorn beetles (Agriotes spp.), and red-footed beetle p.

Pterodoptera: Tocusama grasshopper (Locusta migratoria), Kera (Gryllotalpa africana), Oxya yezoensis, Lobster (Oxya japonica), and crickets.

Hymenoptera: Monomorium phalaosis, Black sea ants (Formica fusca japonica), Luriari (Ochtellus puns), Pstomyrex puns, Pseudorme spr. Such as ants, wasps, scallops, and wasps such as wasp (Athalia rosae) and Japanese bee (Athalia japonica).

Nematodes: rice Shin Galle nematode (Aphelenchoides besseyi), strawberry menu nematode (Nothotylenchus acris), sweet potato root-knot nematode (Meloidogyne incognita), northern root-knot nematode (Meloidogyne hapla), Java root-knot nematode (Meloidogyne javanica), soybean cyst nematode (Heterodera glycines), Potato cyst nematode (Globodera rostochiensis), southern nematode crested pea (Pratylenchus coffeae), barley nematode nematode (Pratylenchus neglectus).

Cockroach eyes pests: German cockroaches (Blatella germanica), Black cockroaches (Periplaneta fuliginosa), American cockroaches (Periplaneta americana), Japanese cockroach (Peripraneta bruna)

Mite order pests: Tick spider mites (Tetranychus urticae), Tick spider mites (Tetranychus kanzawai), citrus spider mite (Pananychus citri), mite spider mite (Panthonychus ulmi), prickly mite pistols, citrus urticae Tomato rust mites (Aculops lycopersici), Chanosabi mites (Calacarus carinatus), Chanogasabi mite (Acaphylla theevagrans), Green rust mites (Eriophyses chibaensis), Apple scab mites Achulus schizus endali) Fushidani such as, dust mite such as Chanohokoridani (Polyphagotarsonemus latus), southern Hime Himehadani such as spider mites (Brevipalpus phoenicis), Kenagahadani such, longicornis (Haemaphysalis longicornis), Yamatochimadani (Haemaphysalis flava), Taiwan Kaku ticks (Dermacentor taiwanicus ), Tick ticks (Ixodes ovatus), Tick ticks (Ixodes persulcatus), Black legged ticks (Ixodes scapularis), Boophilus microplus, Rhipic mite (Rhipic) phalus sanguineus) ticks such as, Tyrophagus (Tyrophagus putrescentiae), grain mites such as Tyrophagus (Tyrophagus similis), farinae (Dermatophagoides farinae), house dust mite such as pteronyssinus (Dermatophagoides ptrenyssnus), Hosotsumedani (Cheyletus eruditus), Stag Tsumedani ( Tilet mites, such as Cheyletus malaccensis, and Mite thorny (Cheyletus moorei), house dust mite (Ornithonysus bacoti), bird mite (Ornithonysus sylvairum) , Cucumbers such as Dermanysusus gallinae, tsutsugamushi such as Leptotropidum akamushi, and Chiracanthium japonicum, etc.

The pest control agent of the present invention contains the compound of the present invention and an inert carrier. The pest control agent of the present invention is usually a mixture of the compound of the present invention and an inert carrier such as a solid carrier, a liquid carrier, a gaseous carrier, etc., and a surfactant or other formulation adjuvant is added as necessary. Thus, they are formulated into emulsions, oils, powders, granules, wettable powders, flowables, microcapsules, aerosols, smoke agents, poison baits, resin preparations and the like.
The pest control agent of the present invention usually contains 0.01 to 95% by weight of the compound of the present invention.

Examples of solid carriers used for formulation include clays (kaolin clay, diatomaceous earth, bentonite, fusami clay, acidic clay), synthetic hydrous silicon oxide, talc, ceramics, and other inorganic minerals (sericite, quartz, sulfur). , Activated carbon, calcium carbonate, hydrated silica, etc.), fine powders and granules of chemical fertilizers (ammonium sulfate, phosphorous acid, ammonium nitrate, urea, ammonium chloride, etc.), and synthetic resins (polypropylene, polyacrylonitrile, polymethyl methacrylate) Polyester resins such as polyethylene terephthalate, nylon resins such as nylon-6, nylon-11, and nylon-66, polyamide resins, polyvinyl chloride, polyvinylidene chloride, and vinyl chloride-propylene copolymers).

Examples of liquid carriers include water, alcohols (methanol, ethanol, isopropyl alcohol, butanol, hexanol, benzyl alcohol, ethylene glycol, propylene glycol, phenoxyethanol, etc.), ketones (acetone, methyl ethyl ketone, cyclohexanone, etc.), aromatic hydrocarbons. (Toluene, xylene, ethylbenzene, dodecylbenzene, phenylxylylethane, methylnaphthalene, etc.), aliphatic hydrocarbons (hexane, cyclohexane, kerosene, light oil, etc.), esters (ethyl acetate, butyl acetate, isopropyl myristate, Ethyl oleate, diisopropyl adipate, diisobutyl adipate, propylene glycol monomethyl ether acetate, etc.), nitriles (acetonitrile, isobutyrate) Nitriles), ethers (diisopropyl ether, 1,4-dioxane, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether, dipropylene glycol monomethyl ether, 3-methoxy-3-methyl-1-butanol, etc. ), Acid amides (N, N-dimethylformamide, N, N-dimethylacetamide, etc.), halogenated hydrocarbons (dichloromethane, trichloroethane, carbon tetrachloride, etc.), sulfoxides (dimethylsulfoxide, etc.), propylene carbonate and vegetable oil (Soybean oil, cottonseed oil, etc.).

Examples of the gaseous carrier include fluorocarbon, butane gas, LPG (liquefied petroleum gas), dimethyl ether, and carbon dioxide gas.

Examples of the surfactant include nonionic surfactants such as polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, and polyethylene glycol fatty acid ester, and anions such as alkyl sulfonate, alkyl benzene sulfonate, and alkyl sulfate. Surfactant is mentioned.

Examples of other adjuvants for preparation include fixing agents, dispersants, colorants and stabilizers, such as casein, gelatin, saccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, Synthetic water-soluble polymers (polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylic acids, etc.), PAP (isopropyl acid phosphate), BHT (2,6-di-tert-butyl-4-methylphenol), BHA (2-tert- And a mixture of butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol).

The pest control method of the present invention is carried out by applying an effective amount of the compound of the present invention directly to pests and / or to habitats of pests (plants, soil, households, animal bodies, etc.). . In the pest control method of the present invention, the compound of the present invention is usually used in the form of the pest control agent of the present invention.

When the pest control agent of the present invention is used for pest control in the agricultural field, the application amount is usually 1 to 10,000 g in terms of the amount of the compound of the present invention per 10,000 m ² . When the pest control agent of the present invention is formulated into an emulsion, wettable powder, flowable agent, etc., it is usually applied after diluting with water so that the concentration of the compound of the present invention is 0.01 to 10,000 ppm. Granules, powders and the like are usually applied as they are.

These preparations and water dilutions of the preparations may be sprayed directly on pests or plants such as crops to be protected from pests, and in order to control pests that inhabit the soil of cultivated land. You may process to soil.

Also, it can be treated by methods such as wrapping a resin preparation processed into a sheet or string around the crop, stretching it around the crop, or laying it on the stock soil.

When the pest control agent of the present invention is used for controlling pests living in a house, the amount applied is the amount of the compound of the present invention per 1 m ² of treatment area when treated on the surface, usually 0.01. In the case of treatment in a space, the amount of the compound of the present invention per 1 m ³ of the treatment space is usually 0.01 to 500 mg. When the pest control agent of the present invention is formulated into an emulsion, wettable powder, flowable agent, etc., it is usually diluted with water so that the concentration of the compound of the present invention is 0.1 to 1000 ppm, and applied. Apply oils, aerosols, smoke, poison baits, etc. as they are.

The pest control agent of the present invention can be used in farmland where the following “crop” is cultivated.
Agricultural crops: corn, rice, wheat, barley, rye, oat, sorghum, cotton, soybean, peanut, buckwheat, sugar beet, rapeseed, sunflower, sugarcane, tobacco, etc.
Vegetables: Solanum vegetables (eggplants, tomatoes, peppers, peppers, potatoes, etc.), Cucurbitaceae vegetables (cucumbers, pumpkins, zucchini, watermelons, melons, etc.), Brassicaceae vegetables (radish, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage) , Mustard, broccoli, cauliflower, etc.), asteraceae vegetables (burdock, shungiku, artichokes, lettuce, etc.), liliaceae vegetables (leek, onion, garlic, asparagus), celery family vegetables (carrot, parsley, celery, American boofish, etc.) ), Red crustacean vegetables (spinach, chard, etc.), persimmon vegetables (perilla, mint, basil, etc.), strawberry, sweet potato, yam, taro, etc.
Fruit trees: berries (apples, pears, Japanese pears, quince, quince, etc.), nuclear fruits (peaches, plums, nectarines, ume, sweet cherry, apricots, prunes, etc.), citrus (satsuma mandarin, orange, lemon, lime, grapefruit) ), Nuts (chestnut, walnut, hazel, almond, pistachio, cashew nut, macadamia nut, etc.), berries (blueberry, cranberry, blackberry, raspberry, etc.), grape, oyster, olive, loquat, banana, coffee, Date palm, coconut palm, oil palm etc.
Trees other than fruit trees: tea, mulberry, flowering trees (Satsuki, camellia, hydrangea, sasanqua, shikimi, sakura, yurinoki, crape myrtle, snapdragon, etc.), roadside trees (ash, birch, dogwood, eucalyptus, ginkgo, lilac, maple, oak) , Poplar, redwood, fu, sycamore, zelkova, blackfish, Japanese amberjack, moths, pine, pine, spruce, yew, elm, Japanese cypress, etc.), coral jug, dogwood, cedar, cypress, croton, masaki, kanamochi, etc.
Lawn: Shiba (Nasis, Pleurotus, etc.), Bermudagrass (Neurodonidae, etc.), Bentgrass (Oleoptera, Hykonukagusa, Odonoptera, etc.), Bluegrass (Nagahagusa, Oosuzunokatabira, etc.), Fescue (Oonishi nokegusa, Drosophila, etc.) , Grass, etc.), ryegrass (rat, wheat, etc.), anemonefish, blue whale, etc.
Other: Flowers (Rose, Carnation, Chrysanthemum, Eustoma, Gypsophila, Gerbera, Marigold, Salvia, Petunia, Verbena, Tulip, Aster, Gentian, Lily, Pansy, Cyclamen, Orchid, Lily of the valley, Lavender, Stock, Habutton, Primula, Poinsettia, gladiolus, cattleya, daisy, symbidium, begonia, etc.), biofuel plants (Jatropha, Curcas, safflower, Amanazuna, switchgrass, Miscanthus, Kusanoshi, Danchiku, Kenaf, cassava, willow, algae, etc.), ornamental plants, etc. .

“Crop” includes genetically modified crops.

The pest control agent of the present invention can be mixed or used in combination with other insecticides, acaricides, nematicides, fungicides, plant growth regulators, herbicides and synergists. Examples of active ingredients of such insecticides, acaricides, nematicides, fungicides, herbicides and synergists are shown below.

Active Ingredient of Insecticide (1) Organophosphorus Compound Acephate, Aluminum Phosphide, Butathiofos, Cadusafos, Chlorethoxyfos, Chlorfenvinphos, Chlorfenvinphos (Chlorpyrifos), Chlorpyrifos-methyl (Chlorpyrifos-methyl), Cyanophos (Cyanophos: CYAP), Diazinon (Diazinon), DCIP (Dichlorodiisopropylene ether), Diclofenthion (V: D) ), Dimethoate, dimethylvinphos, disulfoton, EPN, etion, ethoprofos, etrimfos, fention (MPP), EP, Phosthiazate, formothion, hydrogen phosphide, isofenphos, isoxathion, malathion, methulfenthion, thifenfothone MTP), monocrotophos, nared (BRP), oxydeprofos (ESP), parathion, fosarone, phosmet (PMP), pirimiphosmethyl (pirimifion) (Pyridafenthion), quinalphos, phentoate (PAP), profenofos, propopafos, prothiofos, pyraclofos, phosphite, sulthio Tebupirimfos, temefos, tetrachlorbinphos (tetrach1orvinphos), terbufos, thiomethon, trichlorfon (DEP), bamidithios (vamidothionate, vamidothionate) .
(2) Carbamate compounds alaniccarb, bendiocarb, benfuracarb, BPMC, carbaryl (carbary1), carbofuran, carbothofen, loecarb , Fenobucarb, phenothiocarb, phenoxycarb, furathiocarb, isoprocarb (MIPC), methocarb, methocarb hiocarb, NAC, oxamyl, pirimicarb, propoxur (PHC), XMC, thiodicarb, xylylcarb, and aldicarb.
(3) pyrethroid compounds acrinathrin, allethrin, benfluthrin, beta-cyfluthrin, bifenthrin, cycloprotorin, fluprothrin (cycloprothrin) , Cypermethrin, deltamethrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucitrate f lucytrinate, flufenprox, flumethrin, fluvalinate, halfenprox, imiprothrin, permethrin, praretrin, praretrin resmethrin, sigma-cypermethrin, silafluofen, tefluthrin, tralomethrin, transfluthrin, tetramethrin thrin), phenothrin, cyphenothrin, alpha-cypermethrin, zeta-cypermethrin, lambda cihalothrin (lamdadahalothrin) ), Furamethrin, tau-fluvalinate, methfluthrin, profluthrin, dimethylfluthrin, 2,3,5,6-tetrafluoro-4- (methoxymethyl) benzyl EZ)-(1RS, 3RS; 1RS, 3S ) -2,2-dimethyl-3-prop-1-enylcyclopropanecarboxylate, 2,3,5,6-tetrafluoro-4-methylbenzyl (EZ)-(1RS, 3RS; 1RS, 3SR) -2 , 2-Dimethyl-3-prop-1-enylcyclopropanecarboxylate and 2,3,5,6-tetrafluoro-4- (methoxymethyl) benzyl (1RS, 3RS; 1RS, 3SR) -2,2- Dimethyl-3- (2-methyl-1-propenyl) cyclopropanecarboxylate.
(4) Nereistoxin compounds Cartap, bensultap, thiocyclam, monosultap, and bisultap.
(5) Neonicotinoid compounds imidacloprid (imidac1oprid), nitenpyram (nitenpyram), acetamiprid (acetamipride), thiamethoxam, thiacloprid (thiacloprid), dinoteurin (dinothurine)
(6) Benzoylurea compound Chlorfluazuron, bistrifluron, diafenthiuron, diflubenzuron, fluazuron, flucycloxuron, flucyclolone (Flufenoxuron), hexaflumuron, lufenuron, novaluron, novifluuron, teflubenzuron, triflumuron, and triflumuron.
(7) Phenylpyrazole compounds Acetoprole, etiprole, fipronil, vaniliprole, pyriprole, and pyrafluprole.
(8) Bt toxin Live spores and produced crystal toxins derived from Bacillus thuringiensis, and mixtures thereof;
(9) Hydrazine compounds Chromafenozide, halofenozide, methoxyphenozide, and tebufenozide.
(10) Organochlorine compounds Aldrin, dieldrin, dienochlor, endosulfan, and methoxychlor.
(11) Other Insecticide Active Ingredients Machine oil, nicotine-sulfate; avermectin, bromopropyrate, buprofezin, chlorfenapyr, chlorphenapyr Riproline (cyantraniliprole), cyromazine (cyromazine), DD (1,3-Dichloropropene), emamectin benzoate (emectectin-benzoate), phenazaquin (fenazoquine), flupiroprene Indoxacarb, methoxadiazone, milbemycin-A, pymetrozine, pyridalyl, flurapyr, pyramidine, pyrosylul ), Triazemate, fulvendiamide, repimectin, arsenous acid, benclothiaz, lime nitrogen (Calcium cyanamide), lime sulfur compound lfide), chlordane, DDT, DSP, flufenerium, flonicamid, flurimfen, formatenate, metham-ammonium, metam-ammonium sodium, methyl bromide, potassium oleate, protrifenbute, spiromesifen, sulfoxafluor, sulfur, metafluon, sulfur ), Spirotetramat (spi) otetramat), pyrifluquinazon (pyrifluquinazone), spinetoram (spinetoram), chlorantraniliprole (chlorantraniliprole), Toraropiriru (tralopyril), cyan tiger Niri Prowl (cyantraniliprole),
Following formula (K)

[Where,
R ¹⁰⁰ represents a chlorine, bromine or trifluoromethyl group,
R ²⁰⁰ represents a chlorine, bromine or methyl group,
R ³⁰⁰ represents chlorine, bromine or a cyano group. ]
And a compound represented by the following formula (L)

[Where,
R ¹⁰⁰⁰ represents chlorine, bromine or iodine. ]
A compound represented by

Active ingredients of acaricides: acequinocyl, amitraz, benzoximate, bifenaate, phenisobromolate, chinomethionate BS, chloromethionate BS chlorfenson, clofentezine, cyflumetofene, kelsen (dicofol), etoxazole, fenbutatin oxide, fenothiocarbene roximate, fluacrylpyrim, fluproxyfen, hexythiazox, propargite (BPPS), polynactin complex (pyridene), pyridaben (pyriben) (Tetradifon), spirodiclofen, spiromesifen, spirotetramat, amidoflumet, and cenopyrafen.

Active ingredients of nematicides DCIP, fostiazate, levamisole hydrochloride, methylisothiocyanate, morantel tartrate, and imiciafos.

Antibacterial active ingredients propiconazole, prothioconazole, triadimenol, prochloraz, penconazole, tebuconazole, tebuconazole, tebuconazole, tebuconazole , Bromuconazole, epoxiconazole, difenoconazole, cyproconazole, metconazole, triflumazole, triflumizole Tetraconazole, microbutanil, fenbuconazole, hexaconazole, fluquinconazole, triticonazole, triticonazole, triticonazole, triticonazole, triticonazole, triticonazole Azole fungicidal compounds such as flutriafol;
Cyclic amine bactericidal compounds such as fenpropimorph, tridemorph, fenpropidin;
Benzimidazolic fungicidal compounds such as carbendezim, benomyl, thiabendazole, thiophanate-methyl;
Procymidone; cyprodinil; pyrimethanil; dietofencarb; thiuram; fluazilonyl; Captan; mepanipyrim; fenpiclonil; fludioxonil; diclofluraned; folppet; cresoxime- azoxystrobin; trifloxystrobin; fluoxastrobin; picoxystrobin; pyracrostrobin; dimoxystrobin; dimoxystrobin; dimoxystrobin; Pyribencarb; spiroxamine; quinoxyfen; fenhexamid; famoxadone; fenamidone; samamide; samamide; iprovalicarb; benthiavaricarb; cyazofamid; mandipropamid; boscaliden; (Bixafen); cyflufenamide; proquinazid; isotianil and thiadinil.

Active ingredient of herbicide (1) Phenoxy fatty acid herbicidal compound 2,4-PA, MCP, MCPB, phenthiol (phenothio1), mecoprop, fluroxypyr, triclopyr, clomeprop Naproanilide.
(2) Benzoic acid herbicidal compound 2,3,6-TBA, dicamba, clopyralid, picloram, aminopyralid, quinclorac, and quinmerac.
(3) Urea herbicidal compounds diuron, linuron, chlortoluron, isoproturon, fluometuron, isouron, tebuthiuron, tebuthiuron, metabenthuron , Cumyluron, daimuron, and methyl-daimuron.
(4) Triazine herbicidal compounds atrazine, ametrine, cyanazine, simazine, propazine, simetrin, dimetamethrin (dimetrimetrin) ), Triaziflam, and indaziflam.
(5) Bipyridinium herbicidal compound paraquat and diquat.
(6) Hydroxybenzonitrile herbicidal compounds bromoxynil and ioxynil.
(7) Dinitroaniline herbicidal compound pendimethalin, prodiamine, and trifluralin.
(8) Organophosphorus herbicidal compounds amiprofos-methyl, butamifos, bensulide, piperophos, anilofos, glyphosate, glufosinate, glufosinate, glufosinate P (glufosinate-P), and bialaphos.
(9) Carbamate herbicidal compounds: di-allate, tri-allate, EPTC, butyrate, beniocarb, esprocarb, molinate, dimipeperate (Swep), chlorpropham, phenmedifam, phenisopham, piributicalb, and asuram.
(10) Acid amide herbicidal compounds propanil, propyzamide, bromobutide, and etobenzanide.
(11) Chloroacetanilide herbicidal compounds acetochlor, acechlor, butachlor, dimethenamide, propachlor, metazachlor, metrachlor or totrachlor pretilachor), tenylchlor (theny1ch1or), and petoxamide.
(12) Diphenyl ether herbicidal compounds aciflufen-sodium, bifenox, oxyfluorfen, lactofen, fomesafen, clomethoxythonifen, and clomethoxythonipheni.
(13) Cyclic imide herbicidal compounds oxadiazon, cinidon-ethyl, carfentrazone-ethyl, sulfentrazone, full-microlac-pentyl, flumi-lacyl-pentyl Oxazine (flumioxazin), pyraflufen-ethyl, oxadiargyl (oxadiargy1), pentoxazone (pentoxazone), fluthiacet-methyl (butafenzilben) zone), and saflufenacil (saflufenacil).
(14) Pyrazole herbicidal compounds benzofenap, pyrazolate, pyrazoxifene, topramzone, and pyrasulfotole.
(15) Triketone herbicidal compounds isoxaflutole, benzobicyclon, sulcotrione, mesotrione, tembotrione, and tefriltrione.
(16) Aryloxyphenoxypropionic acid herbicidal compound clodinafop-propargyl, cyhalofop-butyl, diclohop-methyl, phenoxaprop-ethyl, fenoxaprop-propyl Fluazifop-butyl, haloxyhop-methyl, and quizalofop-ethyl, metamihop.
(17) Trione oxime herbicidal compounds alloxydim-sodium, cetoxydim, butroxydim, crestodim, cloproxidim, cyclohexyloxydim (Traxydim), and profoxidim.
(18) A sulfonylurea herbicidal compound chlorsulfuron, sulfomethuron-methyl, metsulfuron-methyl, chlorimuron-ethyl, trivenuron methyl (18) tribenuron-methyl, triasulfuron, bensulfuron-methyl, thifensulfuron-methyl, pyrazosulfuron-methyl, urmisyl-uryl Nicosulfuron (nico) ulfuron, amidosulfuron, cinosulfuron, imazosulfuron, rimsulfuron, halosulfuron (thulfuron), prosulfuron (thulsulfuron), prosulfuron (thulsulfuron) , Triflusulfuron-methyl, flazasulfuron, cyclosulfamuron, flupirsulfuron, sulfosulfurium, sulfosulfurimuron Azulsulfuron, ethoxysulfuron, oxasulfuron, iodosulfuron-methyl-sodium, foramsulfuron, mesosulfuron, mesulfuron methyl Trisulfoxysulfuron, tritosulfuron, orthosulfamuron, flucetosulfuron, and propyrisulfuron.
(19) Imidazolinone herbicidal compounds imazametabenz-methyl, imazamethapyr, imazamox, imazapyr, imazapir, imazakin, and imazaquin
(20) Sulfonamide herbicidal compounds flumetslam, metosulam, dicloslam, floraslam, chloransrammethyl, penoxsulox, penoxsulox, and penoxsulox.
(21) Pyrimidinyloxybenzoic acid herbicidal compound pyrithiobac-sodium, bispyribac-sodium, pyriminobac-methyl1), pyribenzoximid, pyrifalidomid And pyrimisulfan.
(22) Other herbicidal compounds bentazone, bromacil, terbacil, chlorthiamid, isoxaben, dinoseb, amitrol, cinmethyline, cinmethyline (cinthyl) tripiphane, dalapon (da1apon), diflufenzopyr sodium (diflufenzopyr-sodium), dithiopyr (dithiopyr), thiazopyr (thiazopyr), sodium flucarbazone (proflubazone) Nasset (mefenacet), flufenacet (flufenacet), fentrazamide (fentrazamide), caffenstrole (cafenstrom), indanophan (indanofan), oxadichromemephone (oxaneclomefone), fidarate (benduresate) (Norflurazon), flurtamon, diflufenican, picolinafene, beflubutamid, clomazone, amicarbazone , Pinoxaden (pinoxaden), pyraclonil (pyraclonil), pyroxasulfone (pyroxasulfone), thien-carbazone methyl (thiencarbazone-methyl), amino cyclo Pila crawl (aminocyclopyrachlor), type phen carbazone (ipfencarbazone), and Mechiozorin (methiozolin).

Active ingredient of synergist piperonyl butoxide, sesamex, sulfoxide, N- (2-ethylhexyl) -8,9,10-trinorborn-5-ene-2,3-di Carboximide (MGK 264), N-decrimimidazole (N-decylimidazole), WARF-anti-resistant, TBPT, TPP, IBP, PSCP, methyl iodide (CH ₃ I), t-phenyl butyl Tenon (t-phenylbutone), diethyl maleate, DMC, FDMC, ETP, and ETN.

Hereinafter, the present invention will be described in more detail with reference to production examples, formulation examples, test examples, and the like, but the present invention is not limited to these examples.

First, production examples of the compound of the present invention are shown below. In the production examples, Ph represents a phenyl group.

Production Example 1
To a mixture of 11.1 g of 1,2,4-triazole, 20 mL of acetonitrile and 20.7 g of N-ethyldiisopropylamine, 7.34 g of 4,5,6-trichloropyrimidine was added at room temperature. The mixture was stirred at room temperature for 2 hours. The reaction mixture was filtered to collect the solid. This solid was washed with acetonitrile and then dried to obtain 8.24 g of 5-chloro-4,6-bis ([1,2,4] triazol-1-yl) -pyrimidine.
5-Chloro-4,6-bis ([1,2,4] triazol-1-yl) -pyrimidine

¹ H-NMR (CDCl ₃ ) δ: 8.26 (2H, s), 8.98 (1H, s), 9.12 (2H, s).
To a mixture of 0.25 g of 5-chloro-4,6-bis ([1,2,4] triazol-1-yl) -pyrimidine, 2 mL of NMP and 0.2 g of 4-amino-N-tert-butoxycarbonyl-piperidine DBU 0.18g was added under ice cooling, and it stirred under ice cooling for 30 minutes. The reaction mixture was poured into water, and the precipitated crystals were collected by filtration. The obtained crystals were dissolved in ethyl acetate, washed successively with saturated aqueous ammonium chloride and water, dried over magnesium sulfate, and the following formula

0.29 g of the compound represented by the formula (present compound 1) was obtained.

Production Example 2
To a mixture of 2.65 g of 1,2,4-triazole, 10 mL of acetonitrile and 4.96 g of N-ethyldiisopropylamine, 2.61 g of 4,6-dichloro-5-methylpyrimidine was added at room temperature. The mixture was heated to reflux for 14 hours. The cooled reaction mixture was filtered to collect the solid. This solid was washed with acetonitrile and then dried to obtain 2.12 g of 5-methyl-4,6-bis ([1,2,4] triazol-1-yl) -pyrimidine.
5-Methyl-4,6-bis ([1,2,4] triazol-1-yl) -pyrimidine

¹ H-NMR (DMSO-D ₆ ) δ: 2.56 (3H, s), 8.45 (2H, s), 9.11 (1H, s), 9.40 (2H, s).
To a mixture of 4.56 g of 5-methyl-4,6-bis ([1,2,4] triazol-1-yl) -pyrimidine, 40 mL of NMP and 4.01 g of 4-amino-N-tert-butoxycarbonyl-piperidine 3.65 g of DBU was added under ice cooling. The mixture was stirred at 70 ° C. for 6 hours. Water was poured into the reaction mixture cooled to room temperature, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with a saturated aqueous ammonium chloride solution and water, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography.

2.28 g of the compound represented by (present compound 55) was obtained.
To a mixture of 0.36 g of the present compound 55 and 3 mL of DMF was added 0.06 g of 60% sodium hydride (oil) followed by 0.3 g of methyl iodide. The mixture was stirred at room temperature for 2 hours. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with a saturated aqueous ammonium chloride solution and water, dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography.

0.18 g of the compound represented by the formula (present compound 11) was obtained.

Production Example 3
To a mixture of 4.09 g of imidazole, 10 mL of acetonitrile and 3.67 g of 4,5,6-trichloropyrimidine, 7.76 g of N, N-diisopropylethylamine was added under ice cooling. The mixture was left overnight at room temperature. The reaction mixture was filtered to collect the solid. This solid was washed with acetonitrile and then dried to obtain 3.20 g of 5-chloro-4,6-di (imidazol-1-yl) -pyrimidine.
5-Chloro-4,6-di (imidazol-1-yl) -pyrimidine

¹ H-NMR (CDCl ₃ ) δ: 7.26-7.27 (2H, m), 7.83-7.84 (2H, m), 8.49-8.50 (2H, m), 8 .89 (1H, s).
To a mixture of 0.25 g of 5-chloro-4,6-di (imidazol-1-yl) -pyrimidine, 3 mL of NMP and 0.20 g of 4-amino-N-tert-butoxycarbonyl-piperidine was added DBU 0. 2g was added. The mixture was stirred at room temperature for 2 hours and stirred at 100 ° C. for 3 hours. Water was poured into the reaction mixture cooled to room temperature, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with a saturated aqueous ammonium chloride solution and water, dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography.

0.3 g of the compound represented by the present invention (Compound 12 of the present invention) was obtained.

Production Example 4
To a mixture of 4.14 g of 1,2,4-triazole, 30 mL of acetonitrile and 7.75 g of N-ethyldiisopropylamine, 3.41 g of 5-bromo-4,6-dichloropyrimidine was added at room temperature. The mixture was stirred at room temperature for 8 hours. The reaction mixture was filtered to collect the solid. This solid was washed with acetonitrile and then dried to obtain 2.46 g of 5-bromo-4,6-bis ([1,2,4] triazol-1-yl) -pyrimidine.
5-Bromo-4,6-bis ([1,2,4] triazol-1-yl) -pyrimidine

¹ H-NMR (DMSO-D ₆ ) δ: 8.47 (2H, s), 9.26 (1H, s), 9.35 (2H, s).
To a mixture of 0.29 g of 5-bromo-4,6-bis ([1,2,4] triazol-1-yl) -pyrimidine, 3 mL of NMP and 0.20 g of 4-amino-N-tert-butoxycarbonyl-piperidine Under ice cooling, 0.2 g of DBU was added. The mixture was stirred at room temperature for 2 hours. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with a saturated aqueous ammonium chloride solution and water, dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography.

0.29 g of the compound represented by the formula (present compound 15) was obtained.

Production Example 5
To a mixture of 4.99 g of Compound 1 of the present invention and 25 mL of acetonitrile, a mixture of 20 mL of concentrated hydrochloric acid and 20 mL of isopropanol was added. The mixture was stirred at room temperature for 2 hours. The precipitated crystals were collected by filtration, washed with 20 mL of acetonitrile, and the obtained crystals were dried to give (5-chloro-6- [1,2,4] triazol-1-yl-pyrimidin-4-yl) -piperidine. 3.98 g of -4-yl-amine hydrochloride was obtained.
(5-Chloro-6- [1,2,4] triazol-1-yl-pyrimidin-4-yl) -piperidin-4-yl-amine hydrochloride

¹ H-NMR (DMSO-D ₆ ) δ: 1.82-2.06 (4H, m), 2.93-3.09 (2H, m), 3.23-3.40 (2H, m) , 4.27-4.40 (1H, m), 8.34 (1H, s), 8.48 (1H, s), 8.87 (1H, brs), 9.00 (1H, brs), 9.16 (1H, s).
Triethylamine was added to a mixture of 0.36 g of (5-chloro-6- [1,2,4] triazol-1-yl-pyrimidin-4-yl) -piperidin-4-yl-amine hydrochloride and 3 mL of NMP under ice cooling. 0.6 g was added, followed by 0.16 g of 3,3-dimethylbutyryl chloride. The mixture was stirred at 50 ° C. for 2 hours. Water was poured into the reaction mixture cooled to room temperature, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with a saturated aqueous ammonium chloride solution and water, dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography.

0.21 g of the compound represented by the formula (present compound 31) was obtained.

Production Example 6
Triethylamine was added to a mixture of 0.36 g of (5-chloro-6- [1,2,4] triazol-1-yl-pyrimidin-4-yl) -piperidin-4-yl-amine hydrochloride and 3 mL of NMP under ice cooling. 0.6 g was added followed by 0.11 g of tert-butyl isocyanate. The mixture was stirred at room temperature for 2 hours. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with a saturated aqueous ammonium chloride solution and water, dried over sodium sulfate, and concentrated under reduced pressure. The obtained crystals were washed with 6 mL of tert-butyl methyl ether,

0.32 g of the compound represented by the formula (present compound 36) was obtained.

Production Example 7
To a mixture of 0.25 g of 5-chloro-4,6-bis ([1,2,4] triazol-1-yl) -pyrimidine, 3 mL of NMP and 0.19 g of 3-amino-N-tert-butoxycarbonyl-pyrrolidine DBU 0.18g was added under ice-cooling. The mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed successively with a saturated aqueous ammonium chloride solution and water, dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography.

0.24 g of the compound represented by the formula (Compound 42 of the present invention) was obtained.

Production Example 8
To a mixture of 2.13 g of the present compound 55 and 10 mL of acetonitrile, a mixture of 10 mL of concentrated hydrochloric acid and 10 mL of isopropanol was added. The mixture was stirred at room temperature for 1 day. The precipitated crystals are collected by filtration, washed with 5 mL of acetonitrile and dried to give (5-methyl-6- [1,2,4] triazol-1-yl-pyrimidin-4-yl)- 1.66 g of piperidin-4-yl-amine hydrochloride were obtained.
(5-Methyl-6- [1,2,4] triazol-1-yl-pyrimidin-4-yl) -piperidin-4-yl-amine hydrochloride

¹ H-NMR (DMSO-D ₆ ) δ: 1.78-1.94 (2H, m), 1.98-2.08 (2H, m), 2.15 (3H, s), 2.91 -3.08 (2H, m), 3.26-3.41 (2H, m), 4.25-4.37 (1H, m), 7.26-7.37 (1H, m), 8 .29 (1H, s), 8.40 (1H, s), 9.05 (2H, brs), 9.10 (1H, s).
Triethylamine was added to a mixture of 0.33 g of (5-methyl-6- [1,2,4] triazol-1-yl-pyrimidin-4-yl) -piperidin-4-yl-amine hydrochloride and 3 mL of NMP under ice cooling. 0.6 g was added followed by 0.11 g of tert-butyl isocyanate. The mixture was stirred at room temperature for 2 hours. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with a saturated aqueous ammonium chloride solution and water, dried over sodium sulfate, and concentrated under reduced pressure. The obtained crystals were washed with 5 mL of acetonitrile,

0.24 g of the compound represented by the formula (present compound 43) was obtained.

Production Example 9
Triethylamine was added to a mixture of 0.36 g of (5-chloro-6- [1,2,4] triazol-1-yl-pyrimidin-4-yl) -piperidin-4-yl-amine hydrochloride and 3 mL of NMP under ice cooling. 0.6 g was added followed by 0.08 g of N, N-diethylcarbamoyl chloride. The mixture was stirred at room temperature for 1 day. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with a saturated aqueous ammonium chloride solution and water, dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography.

0.15 g of the compound represented by the formula (present compound 46) was obtained.

Production Example 10
A mixture of 0.25 g of 5-chloro-4,6-bis ([1,2,4] triazol-1-yl) -pyrimidine, 2 mL of NMP and 0.22 g of 4-aminomethyl-N-tert-butoxycarbonyl-piperidine To this was added 0.20 g of DBU under ice cooling. The mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed successively with a saturated aqueous ammonium chloride solution and water, dried over sodium sulfate, and concentrated under reduced pressure. The obtained crystals were washed with tert-butyl methyl ether,

0.18 g of the compound represented by the formula (present compound 51) was obtained.

Production Example 11
To a mixture of 0.83 g of 1,2,4-triazole, 10 mL of acetonitrile and 0.96 g of 4,6-dichloro-5-methoxypyrimidine, 1.83 g of DBU was added at room temperature. The mixture was stirred at room temperature for 2 hours. 1 mL of water was added to the reaction mixture, and the crystals were collected by filtration and dried to obtain 0.56 g of 5-methoxy-4,6-bis ([1,2,4] triazol-1-yl) -pyrimidine. .
5-Methoxy-4,6-bis ([1,2,4] triazol-1-yl) -pyrimidine

¹ H-NMR (CDCl ₃ ) δ: 3.91 (3H, s), 8.28 (2H, s), 8.87 (1H, s), 9.26 (2H, s).
To a mixture of 0.24 g of 5-methoxy-4,6-bis ([1,2,4] triazol-1-yl) -pyrimidine, 3 mL of NMP and 0.20 g of 4-amino-N-tert-butoxycarbonyl-piperidine DBU 0.18g was added under ice-cooling. The mixture was stirred at room temperature for 1 day. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed successively with a saturated aqueous ammonium chloride solution and water, dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography.

0.09 g of the compound represented by (the present compound 54) was obtained.

Production Example 12
Triethylamine was added to a mixture of 0.36 g of (5-chloro-6- [1,2,4] triazol-1-yl-pyrimidin-4-yl) -piperidin-4-yl-amine hydrochloride and 3 mL of NMP under ice cooling. 0.6 g was added followed by 0.14 g of methanesulfonyl chloride. The mixture was stirred at 60 ° C. for 2 hours. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with a saturated aqueous ammonium chloride solution and water, dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography.

0.06 g of the compound represented by (the present compound 56) was obtained.

Production Example 13-1
Triethylamine was added to a mixture of 0.36 g of (5-chloro-6- [1,2,4] triazol-1-yl-pyrimidin-4-yl) -piperidin-4-yl-amine hydrochloride and 3 mL of NMP under ice cooling. 0.6 g was added followed by 0.17 g of tert-butylsulfinyl chloride. The mixture was stirred at 60 ° C. for 2 hours. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with a saturated aqueous ammonium chloride solution and water, dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography.

In this manner, 0.15 g of the compound represented by (Compound 57A) was obtained.
¹ H-NMR (CDCl ₃ ) δ: 1.20 (9H, s), 1.56-1.72 (2H, m), 2.08-2.19 (2H, m), 2.93-3 .13 (2H, m), 3.45-3.60 (2H, m), 4.20-4.32 (1H, m), 5.75 (1H, d), 8.17 (1H, s ), 8.42 (1H, s), 8.97 (1H, s).

Production Example 13-2
To a mixture of 0.15 g of compound 57A and 5 mL of chloroform, 0.46 g of 3-chloroperbenzoic acid was added under ice cooling. The mixture was stirred at room temperature for 2 hours. A saturated aqueous sodium thiosulfate solution was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution, dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography.

0.14 g of the compound represented by the formula (Compound 57 of the present invention) was obtained.

The compounds of the present invention produced in the same manner as in the production method are shown in the table.

The compound of the present invention represented by formula (1).

In the formula, Z-Cyc-A-NR ⁵ — group, R ¹ , R ² , R ³ , R ⁴ and G ¹ represent the combinations described in the following [Table 2].

The ¹ H-NMR data of the compounds of the present invention described in [Table 2] are shown below.

Compound 1 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 1.40-1.54 (11H, m), 2.00-2.15 (2H, m), 2.84-3.10 (2H, m), 4 .00-4.36 (3H, m), 5.61-5.79 (1H, m), 8.17 (1H, s), 8.42 (1H, s), 8.97 (1H, s ).
Compound 2 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 1.30-1.49 (11H, m), 1.95-2.03 (2H, m), 2.87-3.01 (2H, m), 3 97-4.16 (2H, m), 4.18-4.30 (1H, m), 5.35-5.45 (1H, m), 7.86 (1H, s), 8.10 (1H, s), 8.27 (1H, s), 8.53 (1H, s), 9.10 (1H, s).
Compound 3 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 1.36-1.51 (11H, m), 2.03-2.10 (2H, m), 2.91-3.05 (2H, m), 3 .82-4.22 (3H, m), 4.99-5.34 (1H, m), 6.83 (1H, s), 8.09 (1H, s), 8.44 (1H, s ), 9.15 (1H, s).
Compound 4 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 1.25 (3H, t), 1.34 to 1.52 (11H, m), 2.06-2.15 (2H, m), 2.78 (2H Q), 2.89-3.04 (2H, m), 4.00-4.20 (2H, m), 4.22-4.35 (1H, m), 4.82-4.93 (1H, m), 8.10 (1H, s), 8.40 (1H, s), 8.97 (1H, s).
Compound 5 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 1.18-1.32 (2H, m), 1.45 (9H, s), 1.91-2.01 (2H, m), 2.84-3 .02 (2H, m), 3.89-4.06 (2H, m), 4.15-4.26 (1H, m), 4.67-4.81 (1H, m), 7.13 -7.20 (2H, m), 7.39-7.54 (3H, m), 7.81 (1H, s), 8.49 (1H, s), 8.57 (1H, s).
Compound 6 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 1.30 (6H, d), 1.39-1.52 (11 H, m), 2.07-2.16 (2H, m), 2.92-3 .12 (2H, m), 3.49-3.64 (1H, m), 4.00-4.15 (2H, m), 4.23-4.40 (1H, m), 4.88 -4.99 (1H, m), 8.09 (1H, s), 8.37 (1H, s), 8.74 (1H, s).
Compound 7 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 1.40-1.55 (11H, m), 2.06-2.13 (2H, m), 2.84-3.03 (2H, m), 4 .03-4.32 (3H, m), 5.20-5.35 (1H, m), 8.19 (1H, s), 8.29 (1H, s), 9.04 (1H, s ).
Compound 8 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 1.36-1.50 (11H, m), 2.01-2.10 (2H, m), 2.90-3.04 (2H, m), 3 .88-4.20 (3H, m), 4.98-5.23 (1H, m), 6.24 (1H, s), 7.18 (1H, s), 7.57 (1H, s) ), 8.35 (1H, s), 8.46 (1H, s).
Compound 9 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 1.35 to 1.53 (11H, m), 1.98-2.10 (2H, m), 2.51 (3H, s), 2.88-3 .05 (2H, m), 3.97-4.18 (2H, m), 6.65 (1H, s), 8.08 (1H, s), 9.16 (1H, s).
Compound 10 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 1.41-1.53 (11H, m), 1.96-2.12 (2H, m), 2.88-3.06 (2H, m), 3 .95-4.22 (2H, m), 4.25-4.43 (1H, m), 6.73-6.88 (1H, m), 8.10 (1H, s), 8.50 (1H, s), 8.97 (1H, s).

Compound 11 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 1.48 (9H, s), 1.73-1.89 (4H, m), 2.29 (3H, s), 2.74-2.91 (2H M), 2.96 (3H, s), 4.03-4.44 (3H, m), 8.12 (1H, s), 8.41 (1H, s), 8.93 (1H, s).
Compound 12 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 1.42-1.51 (11H, m), 2.01-2.13 (2H, m), 2.85-3.05 (2H, m), 3 97-4.33 (3H, m), 5.48-5.57 (1H, m), 7.17-7.20 (1H, m), 7.67-7.71 (1H, m) , 8.34 (1H, s), 8.40 (1H, s).
Compound 13 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 1.40-1.55 (11H, m), 2.01-2.15 (2H, m), 2.89-3.05 (2H, m), 4 .03-4.32 (3H, m), 5.67-5.82 (1H, m), 8.43 (1H, s), 9.00 (1H, s).
Compound 14 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 1.40-1.53 (11H, m), 2.01-2.13 (2H, m), 2.86-3.03 (2H, m), 4 .02-4.32 (3H, m), 5.66-5.78 (1H, m), 8.39 (1H, s), 8.89 (1H, s).
Compound 15 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 1.39-1.53 (11H, m), 2.02-2.14 (2H, m), 2.87-3.05 (2H, m), 4 .01-4.32 (3H, m), 5.77-5.87 (1H, m), 8.16 (1H, s), 8.42 (1H, s), 8.91 (1H, s ).
Compound 16 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 1.46-1.58 (2H, m), 2.14 (3H, s), 2.17-2.26 (2H, m), 2.77-2 .90 (1H, m), 3.21-3.33 (1H, m), 3.81-3.96 (1H, m), 4.25-4.41 (1H, m), 4.56 -4.71 (1H, m), 5.65-5.81 (1H, m), 8.17 (1H, s), 8.43 (1H, s), 8.98 (1H, s).
Compound 17 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 1.44 to 1.55 (2H, m), 2.07-2.15 (2H, m), 2.95-3.11 (2H, m), 3 .72 (3H, s), 3.99-4.36 (3H, m), 5.68-5.76 (1H, m), 8.17 (1H, s), 8.42 (1H, s ), 8.97 (1H, s).
Compound 18 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 0.96 (3H, t), 1.42-1.54 (2H, m), 1.63-1.73 (2H, m), 2.04-2 .16 (2H, m), 2.93-3.11 (2H, m), 4.02-4.11 (2H, m), 4.15-4.35 (3H, m), 5.60 -5.77 (1H, m), 8.17 (1H, s), 8.42 (1H, s), 8.97 (1H, s).
Compound 19 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 0.92-0.99 (3H, m), 1.35-1.44 (2H, m), 1.46-1.54 (2H, m), 1 .60-1.69 (2H, m), 2.05-2.15 (2H, m), 2.92-3.08 (2H, m), 4.07-4.12 (2H, m) 4.15-4.35 (3H, m), 5.63-5.74 (1H, m), 8.17 (1H, s), 8.42 (1H, s), 8.97 (1H , S).
Compound 20 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 1.26 (6H, d), 1.41-1.55 (2H, m), 2.04-2.16 (2H, m), 2.92-3 .06 (2H, m), 4.06-4.36 (3H, m), 4.86-5.01 (1H, m), 5.64-5.75 (1H, m), 8.17 (1H, s), 8.42 (1H, s), 8.97 (1H, s).

Compound 21 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 0.90-1.01 (6H, m), 1.41-1.54 (2H, m), 1.87-2.03 (1H, m), 2 0.06-2.18 (2H, m), 2.91-3.12 (2H, m), 3.81-3.94 (2H, m), 4.07-4.38 (3H, m) , 5.65-5.76 (1H, m), 8.17 (1H, d), 8.43 (1H, d), 8.98 (1H, d).
Compound 22 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 1.58-1.68 (2H, m), 2.14-2.29 (2H, m), 2.97-3.35 (2H, m), 4 .24-4.45 (3H, m), 5.70-5.81 (1H, m), 7.08-7.14 (2H, m), 7.18-7.24 (1H, m) , 7.34-7.42 (2H, m), 8.18 (1H, s), 8.44 (1H, s), 8.99 (1H, s).
Compound 23 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 1.42-1.53 (2H, m), 2.04-2.16 (2H, m), 2.88-3.12 (2H, m), 4 .09-4.39 (3H, m), 4.61 (2H, d), 5.28 (2H, dd), 5.64-5.77 (1H, m), 5.85-6.03 (1H, m), 8.17 (1H, s), 8.42 (1H, s), 8.97 (1H, s).
Compound 24 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 1.45-1.60 (2H, m), 2.07-2.20 (2H, m), 2.46-2.51 (1H, m), 2 97-3.15 (2H, m), 4.05-4.39 (3H, m), 4.69-4.75 (2H, m), 5.65-5.74 (1H, m) , 8.17 (1H, s), 8.42 (1H, s), 8.98 (1H, s).
Compound 25 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 1.46-1.53 (2H, m), 2.03-2.16 (2H, m), 2.90-3.14 (2H, m), 4 .09-4.38 (3H, m), 5.15 (2H, s), 5.64-5.76 (1H, m), 7.33-7.40 (5H, m), 8.17 (1H, s), 8.42 (1H, s), 8.97 (1H, s).
Compound 26 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 1.49-1.63 (2H, m), 2.09-2.24 (2H, m), 2.97-3.23 (2H, m), 4 .14-4.40 (3H, m), 4.62-4.91 (2H, m), 5.64-5.78 (1H, m), 8.17 (1H, s), 8.43 (1H, s), 8.98 (1H, s).
Compound 27 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 1.28 (3H, t), 1.42-1.56 (2H, m), 2.06-2.16 (2H, m), 2.91-3 .11 (2H, m), 4.06-4.36 (5H, m), 5.62-5.77 (1H, m), 8.17 (1H, s), 8.42 (1H, s ), 8.97 (1H, s).
Compound 28 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 1.12-1.22 (3H, m), 1.40-1.54 (2H, m), 2.07-2.27 (2H, m), 2 32-2-244 (2H, m), 2.79-2.89 (1H, m), 3.15-3.29 (1H, m), 3.85-3.98 (1H, m) 4.24-4.38 (1H, m), 4.59-4.72 (1H, m), 5.65-5.75 (1H, m), 8.17 (1H, s), 8 .43 (1H, s), 8.98 (1H, s).
Compound 29 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 0.99 (3H, t), 1.40-1.55 (2H, m), 1.64-1.74 (2H, m), 2.08-2 .24 (2H, m), 2.30-2.39 (2H, m), 2.76-2.89 (1H, m), 3.15-3.30 (1H, m), 3.87 -3.98 (1H, m), 4.24-4.40 (1H, m), 4.59-4.72 (1H, m), 5.62-5.78 (1H, m), 8 .17 (1H, s), 8.42 (1H, s), 8.98 (1H, s).
Compound 30 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 0.95 (3H, t), 1.31-1.44 (2H, m), 1.45-1.55 (2H, m), 1.59-1 .68 (2H, m), 2.07-2.27 (2H, m), 2.30-2.41 (2H, m), 2.75-2.87 (1H, m), 3.16 -3.30 (1H, m), 3.86-4.00 (1H, m), 4.26-4.40 (1H, m), 4.60-4.72 (1H, m), 5 .65-5.77 (1H, m), 8.17 (1H, s), 8.43 (1H, s), 8.98 (1H, s).

Compound 31 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 1.07 (9H, s), 1.42-1.54 (2H, m), 2.07-2.24 (2H, m), 2.27-2 .33 (2H, m), 2.74-2.87 (1H, m), 3.16-3.31 (1H, m), 3.93-4.05 (1H, m), 4.24 -4.37 (1H, m), 4.63-4.77 (1H, m), 5.60-5.77 (1H, m), 8.17 (1H, s), 8.42 (1H , S), 8.98 (1H, s).
Compound 32 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 1.08-1.89 (6H, m), 2.09-2.29 (2H, m), 2.43-2.57 (1H, m), 2 .74-2.87 (1H, m), 3.15-3.32 (1H, m), 3.88-4.04 (1H, m), 4.26-4.41 (1H, m) 4.55-4.75 (1H, m), 5.62-5.80 (1H, m), 8.17 (1H, s), 8.43 (1H, s), 8.98 (1H , S).
Compound 33 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 0.73-0.84 (2H, m), 0.96-1.05 (2H, m), 1.41-1.60 (8H, m), 1 .74-1.84 (1H, m), 2.05-2.30 (2H, m), 2.76-2.96 (1H, m), 3.24-3.45 (1H, m) 4.19-4.45 (2H, m), 4.53-4.71 (1H, m), 5.62-5.83 (1H, m), 8.17 (1H, s), 8 .43 (1H, s), 8.98 (1H, s).
Compound 34 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 0.79-1.88 (13H, m), 2.00-2.29 (4H, m), 2.69-2.86 (1H, m), 3 10-3.29 (1H, m), 3.83-4.00 (1H, m), 4.22-4.38 (1H, m), 4.57-4.74 (1H, m) , 5.61-5.74 (1H, m), 8.15 (1H, s), 8.40 (1H, s), 8.95 (1H, s).
Compound 35 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 1.58-1.72 (2H, m), 2.17-2.31 (2H, m), 3.06-3.37 (2H, m), 4 .23-4.47 (3H, m), 5.69-5.80 (1H, m), 7.30-7.34 (2H, m), 8.18 (1H, s), 8.24 -8.30 (2H, m), 8.44 (1H, s), 8.99 (1H, s).
Compound 36 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 1.37 (9H, s), 1.47-1.55 (2H, m), 2.07-2.17 (2H, m), 2.90-3 .05 (2H, m), 3.85-3.99 (2H, m), 4.19-4.39 (2H, m), 5.64-5.78 (1H, m), 8.17 (1H, s), 8.42 (1H, s), 8.97 (1H, s).
Compound 37 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 0.91 (3H, t), 1.41-1.50 (8H, m), 1.80 (2H, q), 2.01-2.14 (2H M), 2.84-3.07 (2H, m), 3.98-4.35 (3H, m), 5.62-5.77 (1H, m), 8.17 (1H, s) ), 8.42 (1H, s), 8.97 (1H, s).
Compound 38 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 0.96 (9H, s), 1.44-1.55 (2H, m), 2.05-2.19 (2H, m), 2.93-3 .14 (2H, m), 3.80 (2H, s), 4.10-4.39 (3H, m), 5.64-5.77 (1H, m), 8.17 (1H, s ), 8.42 (1H, s), 8.97 (1H, s).
Compound 40 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 1.38-1.53 (11H, m), 2.06-2.16 (2H, m), 2.87-3.03 (2H, m), 4 .02-4.30 (3H, m), 4.57-4.82 (2H, m), 4.85-4.96 (1H, m), 8.14 (1H, s), 8.15 (1H, s), 9.22 (1H, s).

Compound 41 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 1.33-1.54 (11H, m), 2.03-2.15 (2H, m), 2.22 (3H, s), 2.51 (3H , S), 2.86-3.07 (2H, m), 4.02-4.22 (2H, m), 4.24-4.38 (1H, m), 4.62-4.73 (1H, m), 8.09 (1H, s), 8.89 (1H, s).
Compound 42 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 1.48 (9H, s), 1.94-2.03 (1H, m), 2.25-2.40 (1H, m), 3.21-3 .45 (1H, m), 3.49-3.63 (2H, m), 3.75-3.86 (1H, m), 4.64-4.83 (1H, m), 5.76 -5.91 (1H, m), 8.17 (1H, s), 8.45 (1H, s), 8.99 (1H, s).
Compound 43 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 1.37 (9H, s), 1.42-1.53 (2H, m), 2.08-2.18 (2H, m), 2.31 (3H , S), 2.91-3.06 (2H, m), 3.85-3.99 (2H, m), 4.17-4.39 (2H, m), 4.74-4.84 (1H, m), 8.11 (1H, s), 8.42 (1H, s), 8.94 (1H, s).
Compound 44 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 0.91 (3H, t), 1.35 to 1.50 (8H, m), 1.80 (2H, q), 2.05 to 2.15 (2H M), 2.31 (3H, s), 2.89-3.04 (2H, m), 4.05-4.21 (2H, m), 4.23-4.35 (1H, m ), 4.73-4.83 (1H, m), 8.11 (1H, s), 8.42 (1H, s), 8.94 (1H, s).
Compound 45 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 1.51-1.65 (2H, m), 2.07-2.18 (2H, m), 2.86 (6H, s), 2.92-3 .03 (2H, m), 3.62-3.79 (2H, m), 4.18-4.35 (1H, m), 5.63-5.79 (1H, m), 8.17 (1H, s), 8.42 (1H, s), 8.97 (1H, s).
Compound 46 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 1.14 (6H, t), 1.52-1.65 (2H, m), 2.07-2.17 (2H, m), 2.88-3 .06 (2H, m), 3.23 (4H, q), 3.60-3.74 (2H, m), 4.21-4.35 (1H, m), 5.63-5.80 (1H, m), 8.17 (1H, s), 8.42 (1H, s), 8.97 (1H, s).
Compound 47 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 1.29 (12H, d), 1.55-1.65 (2H, m), 2.07-2.14 (2H, m), 2.83-2 .98 (2H, m), 3.47-3.55 (2H, m), 3.58-3.70 (2H, m), 4.19-4.31 (1H, m), 5.66 -5.79 (1H, m), 8.17 (1H, s), 8.42 (1H, s), 8.97 (1H, s).
Compound 48 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 1.17 (6H, d), 1.48-1.58 (2H, m), 2.08-2.19 (2H, m), 2.92-3 .08 (2H, m), 3.90-4.04 (3H, m), 4.18-4.33 (2H, m), 5.64-5.76 (1H, m), 8.17 (1H, s), 8.42 (1H, s), 8.97 (1H, s).
Compound 49 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 1.54-1.67 (11H, m), 2.11-2.25 (2H, m), 3.12-3.28 (2H, m), 4 30-4.45 (1H, m), 4.53-4.66 (2H, m), 5.42-5.48 (1H, m), 5.65-5.78 (1H, m) , 8.17 (1H, s), 8.42 (1H, s), 8.97 (1H, s).
Compound 50 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 1.41-1.63 (14H, m), 2.09-2.22 (2H, m), 2.91-3.07 (2H, m), 3 97-4.36 (3H, m), 5.86-6.00 (1H, m), 8.19 (1H, s), 9.10 (1H, s).

Compound 51 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 1.12-1.31 (2H, m), 1.46 (9H, s), 1.68-1.80 (2H, m), 1.82-1 .93 (1H, m), 2.59-2.83 (2H, m), 3.44-3.59 (2H, m), 3.98-4.31 (2H, m), 5.87 -6.06 (1H, m), 8.17 (1H, s), 8.42 (1H, s), 8.97 (1H, s).
Compound 52 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 1.41-1.52 (11H, m), 2.00-2.12 (2H, m), 2.83-3.01 (2H, m), 4 .03-4.23 (2H, m), 4.26-4.39 (1H, m), 5.79-5.92 (1H, m), 8.22 (1H, s), 8.54 (1H, s), 9.19 (1H, s).
Compound 53 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 1.45-1.50 (11H, m), 2.02-2.12 (2H, m), 2.89-3.01 (2H, m), 4 .04-4.15 (2H, m), 4.18-4.30 (1H, m), 5.69-5.79 (1H, m), 6.19 (2H, brs), 7.62 (1H, s), 8.34 (1H, s).
Compound 54 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 1.43-1.52 (11H, m), 2.02-2.14 (2H, m), 2.88-3.05 (2H, m), 3 .72 (3H, s), 4.04-4.29 (3H, m), 5.44-5.55 (1H, m), 8.18 (1H, s), 8.29 (1H, s ), 9.03 (1H, s).
Compound 55 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 1.38-1.52 (11H, m), 2.06-2.16 (2H, m), 2.31 (3H, s), 2.85-3 .05 (2H, m), 3.99-4.20 (2H, m), 4.23-4.35 (1H, m), 4.71-4.85 (1H, m), 8.11 (1H, s), 8.42 (1H, s), 8.94 (1H, s).
Compound 56 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 1.64-1.78 (2H, m), 2.18-2.27 (2H, m), 2.84 (3H, s), 2.87-2 .97 (2H, m), 3.83-3.92 (2H, m), 4.18-4.30 (1H, m), 5.72 (1H, d), 8.17 (1H, s ), 8.42 (1H, s), 8.98 (1H, s).
Compound 57 of the present invention
¹ H-NMR (CDCl ₃ ) δ: 1.39 (9H, s), 1.62-1.72 (2H, m), 2.09-2.19 (2H, m), 3.09-3 .21 (2H, m), 3.86-3.98 (2H, m), 4.20-4.35 (1H, m), 5.73 (1H, d), 8.17 (1H, s ), 8.41 (1H, s), 8.97 (1H, s).

Next, formulation examples are shown. In addition, a part represents a weight part.

Formulation Example 1
10 parts of any one of compounds 1 to 38 and 40 to 57 of the present invention are dissolved in a mixture of 35 parts of xylene and 35 parts of N, N-dimethylformamide, and 14 parts of polyoxyethylene styryl phenyl ether and dodecylbenzenesulfone are dissolved. Add 6 parts of calcium acid and mix to obtain each emulsion.

Formulation Example 2
4 parts of sodium lauryl sulfate, 2 parts of calcium lignin sulfonate, 20 parts of synthetic silicon hydroxide fine powder and 54 parts of diatomaceous earth are mixed, and 20 parts of any one of the compounds 1 to 38 and 40 to 57 of the present invention are added. Mix to obtain each wettable powder.

Formulation Example 3
To 2 parts of any one of the compounds 1 to 38 and 40 to 57 of the present invention, 1 part of a synthetic silicon hydrous fine powder, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 65 parts of kaolin clay are added and mixed. Next, an appropriate amount of water is added to the mixture, and the mixture is further stirred, granulated by a granulator, and dried by ventilation to obtain each granule.

Formulation Example 4
1 part of any one of the compounds 1 to 38 and 40 to 57 of the present invention is dissolved in an appropriate amount of acetone, and 5 parts of a synthetic silicon hydroxide fine powder, 0.3 part of PAP and 93.7 parts of fusami clay are added thereto. The mixture is sufficiently stirred and mixed, and acetone is removed by evaporation to obtain each powder.

Formulation Example 5
35 parts of a mixture of polyoxyethylene alkyl ether sulfate ammonium salt and white carbon (weight ratio 1: 1), 10 parts of any one of the compounds of the present invention 1 to 38 and 40 to 57, and 55 parts of water are mixed. Each formulation is obtained by finely pulverizing by a wet pulverization method.

Formulation Example 6
0.1 part of any one of the compounds 1 to 38 and 40 to 57 of the present invention is dissolved in 5 parts of xylene and 5 parts of trichloroethane and mixed with 89.9 parts of deodorized kerosene to obtain each oil agent.

Formulation Example 7
10 mg of any one of the compounds 1 to 38 and 40 to 57 of the present invention is dissolved in 0.5 ml of acetone, and this solution is mixed with animal solid feed powder (bred breeding solid feed powder CE-2, Nippon Claire Co., Ltd. ) Process to 5g and mix uniformly. Then, acetone is evaporated to dryness to obtain each poisonous bait.

Formulation Example 8
0.1 part of any one of the compounds 1 to 38 and 40 to 57 of the present invention, 49.9 parts of Neothiozole (Chuo Kasei Co., Ltd.) are placed in an aerosol can, and after mounting an aerosol valve, 25 parts of dimethyl ether, LPG 25 Fill the part, add shaking, and install the actuator to obtain an oil aerosol.

Formulation Example 9
0.6 part of any one of compounds 1 to 38 and 40 to 57 of the present invention, 0.01 part of BHT (2,6-di-tert-butyl-4-methylphenol), 5 parts of xylene, deodorized kerosene 39 parts and 1 part of an emulsifier {Atmos 300 (registered trademark name of Atmos Chemical Co., Ltd.)} and 50 parts of distilled water were filled in an aerosol container, and after attaching a valve, a propellant (LPG) ) 40 parts under pressure to obtain an aqueous aerosol.

Next, the pest control effect of the compound of the present invention is shown by test examples.

Test example 1
The preparation of Compound 1, 15, 36, 37, 42, 43, 46, 51, 54 and 55 of the present invention obtained in Formulation Example 5 was diluted with water so that the active ingredient concentration would be 500 ppm, and the test spray solution Was prepared.
On the other hand, about 60 adult spider mites were released on a perennial seedling seedling planted in a plastic cup (7 days after sowing, the primary leaf development stage) and left for 1 day. The seedlings were each sprayed with 30 ml of the diluted solution.
After 8 days and 13 days after spraying, the number of surviving ticks on the leaves of the periwinkle was investigated, and the control rate was calculated according to the following formula.
Control rate (%) = 100 × {1− (number of surviving ticks in treated area) / (number of surviving ticks in untreated area)}
Here, the untreated group means a group in which a preparation containing no compound of the present invention in Preparation Example 5 was sprayed with a test chemical diluted with the same amount of water as the treated group.
As a result, the treatment group of the test spray solution of the compounds 1, 15, 36, 37, 42, 43, 46, 51, 54 and 55 of the present invention showed a control value of 90% or more after 8 days or 13 days of treatment. .

Test example 2
The preparations of the compounds 13, 22, 43 and 44 of the present invention obtained in Formulation Example 5 were diluted with water so that the active ingredient concentration was 500 ppm to prepare a test drug solution.
10 ml of the test chemical solution was sprayed on rice seedlings in the second leaf development stage planted in a polyethylene cup. After air drying, 20 3-4 instar larvae of the brown planthopper were released and stored in a greenhouse at 25 ° C. Six days later, the number of brown planthoppers infested with rice was investigated, and the control value was determined by the following formula.
Control value (%) = {1− (Cb × Tai) / (Cai × Tb)} × 100
In addition, the character in a formula represents the following meaning.
Cb: number of insects before treatment in the untreated group Cai: number of insects at the time of observation in the untreated group Tb: number of insects before the treatment in the treated group Tai: number of insects at the time of observation in the treated group In Formulation Example 5, it means a group in which a preparation containing no compound of the present invention was sprayed with a test chemical diluted with the same amount of water as the treatment group.
As a result, the treatment group of the test spray solution of the compounds 13, 22, 43 and 44 of the present invention showed a control value of 90% or more.

The compound of the present invention has a control effect against pests and is useful as an active ingredient of a pest control agent.

Claims

Formula (1)

[Where,
R 1 represents a C1-C3 chain hydrocarbon group optionally having one or more halogen, hydrogen, halogen or amino group,
R 2 represents a C1-C3 chain hydrocarbon group optionally having one or more halogens, hydrogen, halogen, hydroxyl group, mercapto group or amino group,
G 1 represents nitrogen or —CR 6 ═ (wherein R 6 represents a C1-C3 chain hydrocarbon group optionally having one or more halogen, hydrogen, halogen or amino group). ,
R 3 represents a C1-C3 chain hydrocarbon group optionally having one or more halogen, hydrogen, halogen, amino group, nitro group or cyano group,
R 4 represents a C1-C6 chain hydrocarbon group which may have one or more halogens, a C3-C8 cycloalkyl group which may have one or more halogens, one or more halogens. C1-C6 alkoxy group which may have, C1-C6 alkylthio group which may have one or more halogens, C1-C6 alkylsulfinyl group which may have one or more halogens, C1-C6 alkylsulfonyl group which may have one or more halogens, C1-C6 alkylamino group which may have one or more halogens, C2 which may have one or more halogens -C8 dialkylamino group, C2-C6 alkylcarbonylamino group optionally having one or more halogens, C2-C6 alkoxycarbonylamino optionally having one or more halogens A C2-C6 alkylcarbonyl group which may have one or more halogens, a C2-C6 alkoxycarbonyl group which may have one or more halogens, and one or more halogens. May have a C2-C6 alkylcarbamoyl group, a C2-C8 dialkylcarbamoyl group optionally having one or more halogens, and one or more atoms or groups selected from the following group α. A phenyl group, a phenoxy group optionally having one or more atoms or groups selected from the following group α, and one or more atoms or groups selected from the following group α: Represents a 6-membered aromatic heterocyclic group, hydrogen, halogen, hydroxyl group, mercapto group, amino group, nitro group, cyano group or formyl group,
R 5 represents a C1-C3 alkyl group which may have one or more halogens or hydrogen,
A represents a methylene group which may have one or more atoms or groups selected from the group consisting of a single bond, a C1-C3 alkyl group and halogen;
Cyc is the following formula J1 or J2

{In the formula, point a represents a bond with A,
R 7 and R 8 are the same or different and each represents a C1-C3 alkyl group or halogen which may have one or more halogens,
p represents any integer of 0 to 9 (provided that when p is an integer of 2 to 9, each R 7 may be different from each other);
q represents an integer of 0 to 7 (provided that when q is an integer of 2 to 7, each R 8 may be different from each other). } Represents a group represented by
Z is the following formula Z1 or Z2

{In the formula, point b represents a bond with the group represented by Cyc,
R 9 represents a C1-C6 chain hydrocarbon group optionally having one or more halogens, a C3-C8 cycloalkyl group optionally having one or more halogens, and one or more halogens. A C4-C8 (cycloalkyl) alkyl group which may have, a phenyl group which may have one or more atoms or groups selected from the following group α, a benzyl group or hydrogen;
L 1 represents a single bond, oxygen, sulfur or —NR 11 — (wherein R 11 represents a C1-C6 chain hydrocarbon group which may have one or more halogens or hydrogen). ,
Q represents oxygen or sulfur,
R 10 represents a C1-C6 chain hydrocarbon group which may have one or more halogens, or hydrogen,
L 2 represents a single bond or —NR 12 — (wherein R 12 represents a C1-C6 chain hydrocarbon group which may have one or more halogen atoms or hydrogen, and L 2 represents In the case of a single bond, R 10 represents a C1-C6 chain hydrocarbon group which may have one or more halogens.
Group α: C1-C6 chain hydrocarbon group optionally having one or more halogens, C1-C6 alkoxy group optionally having one or more halogens, having one or more halogens C1-C6 alkylthio group which may have one, C1-C6 alkylsulfinyl group which may have one or more halogens, C1-C6 alkylsulfonyl group which may have one or more halogens, C1-C6 alkylamino group optionally having one or more halogens, C2-C8 dialkylamino group optionally having one or more halogens, halogen, hydroxyl group, mercapto group, amino group, cyano group and nitro group A group of groups. ]
The pyrimidine compound shown by these.
The pyrimidine compound according to claim 1 , wherein R 1 is hydrogen, R 2 is hydrogen, and G 1 is nitrogen.
The pyrimidine compound according to claim 1 or 2, wherein R 5 is hydrogen.
The pyrimidine compound according to any one of claims 1 to 3, wherein A is a single bond.
The pyrimidine compound according to any one of claims 1 to 4, wherein Cyc is a group represented by J1.
The pyrimidine compound according to any one of claims 1 to 4, wherein Cyc is a group represented by J2.
R 3 is hydrogen, R 4 is a C1-C6 alkyl group optionally having one or more halogens, a C1-C6 alkoxy group optionally having one or more halogens, one or more The pyrimidine compound according to any one of claims 1 to 6, which is a C1-C6 alkylthio group which may have a halogen or a halogen.
The pyrimidine compound according to any one of claims 1 to 7, wherein Z is a group represented by Z1.
Z is a group represented by Z1, R 9 is a branched C1-C6 alkyl group optionally having one or more halogens, L 1 is oxygen or —NR 11 —, and R 11 is The pyrimidine compound according to any one of claims 1 to 8, which is a C1-C6 alkyl group which may have one or more halogens or hydrogen, and Q is oxygen.
Formula (1-vii)

[Wherein R 4 , R 9 , L 1 and Q each represent the definition of claim 1. ]
The pyrimidine compound of Claim 1 shown by these.
R 4 is hydrogen, methyl group, ethyl group, methoxy group, fluorine, chlorine or bromine, R 9 is tert-butyl group or tert-pentyl group, L 1 is oxygen or —NR 11 —, R The pyrimidine compound according to claim 10, wherein 11 is hydrogen and Q is oxygen.
R 1 is a C1-C3 chain hydrocarbon group optionally having one or more halogen, hydrogen or halogen,
R 2 is hydrogen or an amino group,
G 1 is nitrogen or —CR 6 = (where R 6 is hydrogen);
R 3 is a C1-C3 chain hydrocarbon group or hydrogen optionally having one or more halogens,
R 4 is a C1-C6 chain hydrocarbon group optionally having one or more halogens, a C1-C6 alkoxy group optionally having one or more halogens, one selected from the group α A phenyl group optionally having the above atoms or groups, a 5-6 membered aromatic heterocyclic group optionally having one or more atoms or groups selected from the following group α, hydrogen, halogen, An amino group, a nitro group or a cyano group,
R 5 is a C1-C3 alkyl group optionally having one or more halogens or hydrogen,
A is a methylene group which may have one or more atoms or groups selected from the group consisting of a single bond, a C1-C3 alkyl group and halogen;
Cyc is J1 or J2 {p is 0 and q is 0. }, And
Z is Z1 or Z2 {R 9 is a C1-C6 chain hydrocarbon group optionally having one or more halogens; C3-C8 cycloalkyl group optionally having one or more halogens , A phenyl group or a benzyl group which may have one or more atoms or groups selected from group α, and L 1 is a single bond, oxygen or —NR 11 — (wherein R 11 is A C1-C6 chain hydrocarbon group or hydrogen which may have one or more halogens), Q is oxygen or sulfur, and R 10 has one or more halogens. A C1-C6 chain hydrocarbon group, and L 2 is a single bond},
The pyrimidine compound according to claim 1, wherein group α is a nitro group.
R 1 is a C1-C3 alkyl group optionally having one or more halogen, hydrogen or halogen,
R 2 is hydrogen or an amino group,
G 1 is nitrogen or —CR 6 = (where R 6 is hydrogen);
R 3 is a C1-C3 alkyl group or hydrogen;
R 4 is a C1-C6 alkyl group, a C1-C6 alkoxy group, a phenyl group, a 5-6-membered aromatic heterocyclic group, hydrogen, halogen, amino group, nitro group or cyano group,
R 5 is a C1-C3 alkyl group or hydrogen;
A is a single bond or a methylene group,
Cyc is J1 or J2 {p is 0 and q is 0. }, And
Z is Z1 or Z2 {R 9 is a C1-C6 chain hydrocarbon group optionally having one or more halogens, a C3-C8 cycloalkyl group, one or more atoms selected from the group α, or An optionally substituted phenyl group or benzyl group, L 1 is a single bond, oxygen or —NR 11 — (wherein R 11 is a C1-C6 alkyl group or hydrogen); Q is oxygen or sulfur, R 10 is a C1-C6 alkyl group, and L 2 is a single bond.
The pyrimidine compound according to claim 1, wherein group α is a nitro group.
A pest control agent comprising the pyrimidine compound according to any one of claims 1 to 13 and an inert carrier.
Use of the pyrimidine compound according to any one of claims 1 to 13 for controlling pests.
A method for controlling pests, comprising a step of applying an effective amount of the pyrimidine compound according to any one of claims 1 to 13 to pests or pest habitats.