RU2471778C2 - Halogen-containing organosulphur compounds and use thereof - Google Patents

Abstract

FIELD: chemistry.

SUBSTANCE: present invention relates to novel halogen-containing compounds, having an excellent arthropod pest control effect, represented by formula

, where m equals 0 or 1, n equals 0, 1 or 2; A is a C3-C7 cycloalkyl group, optionally substituted with a group selected from groups E1-E3, or a C5-C7 cycloalkenyl group, optionally substituted with a group selected from groups E1-E3; Q is a C1-C5 haloalkyl group containing at least one fluorine atom; R¹ is a hydrocarbon group with a C1-C4 chain, a halogen atom or a hydrogen atom; R² is a hydrocarbon group with a C1-C4 chain, optionally substituted with a halogen atom, a -C(=G)R⁵ group, a cyano group, a halogen atom or a hydrogen atom; R³ and R⁴ denote a hydrogen atom; G is an oxygen atom or a sulphur atom; R⁵ is a C1-C4 alkoxy group, amino group or a hydrogen atom; group E1 is a group of univalent substitutes consisting of a hydrocarbon group with a C1-C6 chain, optionally substituted with a group selected from group L, C3-C6 cycloalkyl group, optionally substituted with a halogen atom, a halogen atom, cyano group and hydroxyl group; group E2 is a group of divalent substitutes whose two valences are formed on one atom, consisting of =O, =NO-R⁶, and =C(R¹¹)R¹²; group E3 is a group of divalent substitutes whose two valences are formed on different atoms, consisting of C2-C6 alkylene group, optionally substituted with a group selected from group L, a C4-C6 alkenylene group, optionally substituted with a group selected from group L, -G-T¹-G- and -J-T¹-G-T²-; where T¹ and T² are identical or different from each other and denote a methylene group or an ethylene group; group L consists of a hydroxyl group, a C1-C4 alkoxy group, optionally substituted with a halogen atom, a C3-C6 alkenyloxy group, optionally substituted with a halogen atom, -C(=O)R⁷, -OC(=O)R⁸ and a halogen atom; R⁶ is a hydrocarbon group with a C1-C4 chain, optionally substituted with a group selected from group L; R⁷ is a hydroxyl group, a C1-C4 alkoxy group or a hydrogen atom; R⁸ is a hydrogen atom; and R¹¹ and R¹² denote either a hydrogen atom. The invention also relates to a pesticide composition based on these compounds and an arthropod pest control method.

EFFECT: obtaining novel halogen-containing organosulphur compounds with an excellent arthropod pest control effect.

22 cl, 118 ex

Description

FIELD OF THE INVENTION

The present invention relates to a halogen-containing organosulfur compound and its use for combating arthropod parasites.

State of the art

To date, many pesticidal compositions for controlling arthropod parasites have already been developed and put into practice. In addition, JP-A 2004-130306 discloses a specific halogen-containing organosulfur compound.

Description of the invention

The objective of the present invention is to develop a new compound having an effective action against arthropod parasites, and its use.

The authors of the present invention conducted extensive research and found a compound that has an effective effect against arthropod parasites. As a result, it was found that the halogen-containing organosulfur compound represented by the following formula (I) has an effective effect against arthropod parasites such as harmful insects and harmful mites. As a result, the present invention was created.

Namely, the present invention provides:

(1) a halogen-containing organosulfur compound represented by the formula (I):

where m is 0, 1 or 2, n is 0, 1 or 2,

A represents a C3-C7 cycloalkyl group optionally substituted with a group selected from the groups E1-E3, or a C5-C7 cycloalkenyl group optionally substituted with a group selected from the groups E1-E3;

Q represents a C1-C5 haloalkyl group containing at least one fluorine atom, or a fluorine atom;

R ¹ and R ³ are the same or different from each other and represent a hydrocarbon group with a chain C1-C4, optionally substituted by a halogen atom, a halogen atom or a hydrogen atom;

R ² and R ⁴ are the same or different from each other and represent a hydrocarbon group with a C1-C4 chain, optionally substituted with a halogen atom, a group -C (= G) R ⁵ , a cyano group, a halogen atom or a hydrogen atom;

G represents an oxygen atom or a sulfur atom;

R ⁵ represents a C1-C4 alkyl group optionally substituted by a halogen atom, a hydroxyl group, a C1-C4 alkoxy group optionally substituted by a halogen atom, a C3-C6 alkenyloxy group optionally substituted by a halogen atom, a C3-C6 alkynyloxy group optionally substituted by a halogen atom, a C1-4 amino group, an amino group optionally substituted by a halogen atom, a di (C1-C4 alkyl) amino group, optionally substituted by a halogen atom, a C2-C5 cyclic amino group, or a hydrogen atom;

group E1 is a group of monovalent substituents consisting of a hydrocarbon group with a C1-C6 chain, an optionally substituted group selected from a L group, a C3-C6 cycloalkyl group, an optionally substituted halogen atom, a group —OR ⁶ , —SR ⁶ , —S (= O ) R ⁶ , -S (= O) ₂ R ⁶ , -C (= O) R ⁷ , -OC (= O) R ⁸ , a halogen atom, a cyano group and a hydroxyl group;

the E2 group is a group of divalent substituents in which two valencies are formed on the same atom, consisting of = O, = NO-R ⁶ , = C = CH ₂ and = C (R ¹¹ ) R ¹² ;

group E3 is a group of divalent substituents in which two valencies are formed on different atoms, consisting of a C2-C6 alkylene group, an optionally substituted group selected from the group L, a C4-C6 alkenylene group, an optionally substituted group selected from the group L, -GT ¹ - G- and -GT ¹ -GT ² -; where T ¹ and T ² are the same or different from each other and represent a methylene group or an ethylene group;

group L consists of a hydroxyl group, a C1-C4 alkoxy group optionally substituted by a halogen atom, a C3-C6 alkenyloxy group optionally substituted by a halogen atom, a C3-C6 alkynyloxy group, optionally substituted by a halogen atom, a group -N (R ⁹ ) R ¹⁰ , C2-C5 cyclic amino group, - C (= O) R ⁷ , —OC (= O) R ⁸ and a halogen atom;

R ⁶ represents a C1-C4 chain hydrocarbon group optionally substituted with a group selected from group L, or a C3-C6 cycloalkyl group optionally substituted with a group selected from group L;

R ⁷ represents a hydroxyl group, a C1-C4 alkoxy group optionally substituted by a halogen atom, a C3-C6 alkenyloxy group optionally substituted by a halogen atom, a C3-C6 alkynyloxy group optionally substituted by a halogen atom, an amino group, a C1-C4 alkylamino group, optionally substituted by a C1-4 alkyl group ) an amino group optionally substituted with a halogen atom, a C2-C5 cyclic amino group, a C1-C4 alkyl group optionally substituted with a halogen atom, or a hydrogen atom;

R ⁸ represents a C1-C4 alkoxy group optionally substituted by a halogen atom, a C3-C6 alkenyloxy group optionally substituted by a halogen atom, a C3-C6 alkynyloxy group optionally substituted by a halogen atom, an amino group, a C1-C4 alkylamino group optionally substituted by a halogen atom, di () optionally substituted by a halogen atom, a C2-C5 cyclic amino group, a C1-C4 alkyl group optionally substituted by a halogen atom, or a hydrogen atom;

R ⁹ and R ¹⁰ are the same or different from each other and represent a C1-C4 alkyl group optionally substituted by a halogen atom, a C3-C6 alkenyl group optionally substituted by a halogen atom, a C3-C6 alkynyl group optionally substituted by a halogen atom, a C3-C6 cycloalkyl group, optionally substituted by a halogen atom, a phenyl group optionally substituted by a halogen atom, or a hydrogen atom; and

R ¹¹ and R ¹² are the same or different from each other and are a C1-C4 alkoxy group optionally substituted with a halogen atom, a C1-C4 hydrocarbon group optionally substituted with a halogen atom, a halogen atom, or a hydrogen atom (hereinafter referred to as " the compound of the present invention ");

(2) a halogen-containing organosulfur compound according to the above (1), wherein Q is a C1-C3 haloalkyl group containing at least one fluorine atom;

(3) a halogen-containing organosulfur compound according to the above (1), wherein Q is a C1-C5 fluoroalkyl group;

(4) a halogen-containing organosulfur compound according to the above (1), wherein Q is a C1-C3 fluoroalkyl group;

(5) a halogen-containing organosulfur compound according to any one of the above (1) to (4), wherein m is 0;

(6) a halogen-containing organosulfur compound according to any one of the above (1) to (4), wherein m is 1;

(7) a halogen-containing organosulfur compound according to any one of the above (1) to (6), wherein n is 0;

(8) a halogen-containing organosulfur compound according to any one of the above (1) to (6), wherein n is 1;

(9) a halogen-containing organosulfur compound according to any one of the above (1) to (6), wherein n is 2;

(10) a halogen-containing organosulfur compound according to any one of the above (1) to (9), wherein R ² is a hydrogen atom;

(11) a halogen-containing organosulfur compound according to any one of the above (1) to (9), wherein R ² is a C1-C4 alkyl group;

(12) a halogen-containing organosulfur compound according to any one of the above (1) to (9), wherein R ² is a cyano group;

(13) a halogen-containing organosulfur compound according to any one of the above (1) to (9), wherein R ² is a group —C (= G) R ⁵ ;

(14) a halogen-containing organosulfur compound according to any one of the above (1) to (9), wherein R ² is a —C (= G) R ⁵ group, G is an oxygen atom, and R ⁵ is an amino group, a C1-C4 alkylamino group, optionally substituted by a halogen atom, a di (C1-C4 alkyl) amino group, optionally substituted by a halogen atom, or a C2-C5 cyclic amino group;

(15) a halogen-containing organosulfur compound according to any one of the above (1) to (9), wherein R ² is a —C (= G) R ⁵ group, G is an oxygen atom, and R ⁵ is an amino group;

(16) a halogen-containing organosulfur compound according to any one of the above (1) to (15), wherein R ¹ is a hydrogen atom or a C1-C4 alkyl group optionally substituted with a halogen atom;

(17) a halogen-containing organosulfur compound according to any one of the above (1) to (15), wherein R ¹ is a halogen atom;

(18) a halogen-containing organosulfur compound according to any one of the above (1) to (17), wherein A is a cyclohexyl group, an optionally substituted group selected from groups E1-E3, or a cyclohexenyl group, optionally substituted with a group selected from groups E1- E3;

(19) a halogen-containing organosulfur compound according to any one of the above (1) to (17), wherein A is a cyclohexyl or cyclohexenyl group which is optionally substituted with a monovalent group selected from the group consisting of a C2-C6 alkynyl group, optionally substituted with a group, selected from the group L, a C2-C6 alkynyl group, an optionally substituted group selected from the group L, a halogen atom and a cyano group;

(20) a halogen-containing organosulfur compound according to any one of the above (1) to (17), wherein A is a cyclohexyl group optionally substituted with a group selected from the group E2;

(21) a pesticidal composition that includes a halogen-containing organosulfur compound according to any one of the above (1) to (20) as an active ingredient; and

(22) a method for controlling an arthropod parasite, which comprises applying an effective amount of a halogen-containing organosulfur compound according to any one of the above (1) to (20) to an arthropod parasite or to the place where the arthropod parasite lives.

Illustrative Embodiment of the Present Invention

As used herein, the term “haloalkyl group” means an alkyl group substituted with one or more halogen atoms selected from the group consisting of fluoro, chloro, bromo and iodo. As used herein, the expression "C1-C6" or other similar means the total number of carbon atoms forming each substituent group.

A C3-C7 cycloalkyl group in the expression “C3-C7 cycloalkyl group optionally substituted with a group selected from E1-E3 groups” in formula (I) is a 3-7 membered saturated carbocyclic group, and examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, cyclohexyl group, cycloheptyl group and cyclooctyl group.

The C5-C7 cycloalkenyl group in the expression “C5-C7 cycloalkenyl group optionally substituted with a group selected from the E1-E3 groups” in formula (I) is a 5-7 membered unsaturated carbocyclic group without the maximum number of double bonds, and examples thereof include 1-cyclopentenyl group, 2-cyclopentenyl group, 3-cyclopentenyl group, 1-cyclohexenyl group, 2-cyclohexenyl group, 3-cyclohexenyl group, 1-cycloheptenyl group, 2-cycloheptenyl group, 3-cycloheptenyl group and 4-cycloheptenyl group uppu.

A C3-C7 cycloalkyl group or a C5-C7 cycloalkenyl group may be substituted by two or more monovalent groups selected from the E1 group, on different carbon atoms or on the same carbon atom of the ring, and two or more monovalent substituents selected from the E1 group may be the same or different from each other. Examples of a cyclohexyl group substituted with two groups selected from group E1 are shown below.

In addition, a C3-C7 cycloalkyl group or a C5-C7 cycloalkenyl group may be substituted by a divalent group selected from the E3 group on different carbon atoms or on the same carbon atom of the ring. Examples of a cyclohexyl group substituted with a group selected from group E3 are shown below.

In group E1, examples of a “hydrocarbon group with a C1-C6 chain optionally substituted with a group selected from group L” include a C1-C6 alkyl group optionally substituted with a group selected from group L, such as methyl group, fluoromethyl group, difluoromethyl group, trifluoromethyl group a group, a 2-propynyloxymethyl group, a 2-butynyloxymethyl group, a hydroxymethyl group and other similar groups; A C2-C6 alkenyl group optionally substituted with a group selected from group L, such as a vinyl group, 2,2-difluorovinyl group, 1-propenyl group, 2-propenyl group and other similar groups; and a C2-C6 alkynyl group optionally substituted with a group selected from group L, such as a 3-methoxy-1-propynyl group, 3-methoxy-1-butynyl group, 4-methoxy-1-butynyl group, 4-methoxy-2- butynyl group, 3-methoxy-1-pentinyl group, 4-methoxy-1-pentinyl group, 5-methoxy-1-pentinyl group, 4-methoxy-2-pentinyl group, 5-methoxy-2-pentinyl group, 5- methoxy-3-pentinyl group, 3-hydroxy-1-propynyl group, 3-hydroxy-1-butynyl group, 4-hydroxy-1-butynyl group, 4-hydroxy-2-butynyl group, 3-hydroxy-1-ne ntinyl group, 4-hydroxy-1-pentinyl group, 5-hydroxy-1-pentinyl group, 4-hydroxy-2-pentinyl group, 5-hydroxy-2-pentinyl group, 5-hydroxy-3-pentinyl group, 3- methylamino-1-propynyl group, 3-methylamino-1-butynyl group, 4-methylamino-1-butynyl group, 4-methylamino-2-butynyl group, 3-methylamino-1-pentinyl group, 4-methylamino-1-pentinyl group, 5-methylamino-1-pentinyl group, 4-methylamino-2-pentinyl group, 5-methylamino-2-pentinyl group, 5-methylamino-3-pentinyl group, 3-dimethylamino-1-p ropinyl group, 3-dimethylamino-1-butynyl group, 4-dimethylamino-1-butynyl group, 4-dimethylamino-2-butynyl group, 3-dimethylamino-1-pentinyl group, 4-dimethylamino-1-pentinyl group, 5- dimethylamino-1-pentynyl group, 4-dimethylamino-2-pentinyl group, 5-dimethylamino-2-pentinyl group, 5-dimethylamino-3-pentinyl group, 3-phenylamino-1-propynyl group, 3-phenylamino-1-butynyl group, 4-phenylamino-1-butynyl group, 4-phenylamino-2-butynyl group, 3-phenylamino-1-pentinyl group, 4-phenylamino-1-pentinyl group, 5-phenylamino-1-pentinyl group, 4-phenylamino-2-pentinyl group, 5-phenylamino-2-pentinyl group, 5-phenylamino-3-pentinyl group, 3-methylphenylamino-1-propynyl group, 3- methylphenylamino-1-butynyl group, 4-methylphenylamino-1-butynyl group, 4-methylphenylamino-2-butynyl group, 3-methylphenylamino-1-pentinyl group, 4-methylphenylamino-1-pentinyl group, 5-methylphenylamino-1-pentinyl group, 4-methylphenylamino-2-pentinyl group, 5-methylphenylamino-2-pentinyl group, 5-methylphenylamino-3-pentinyl group uppa, 3- (1-pyrrolidinyl) -1-propynyl group, 3- (1-pyrrolidinyl) -1-butynyl group, 4- (1-pyrrolidinyl) -1-butynyl group, 4- (1-pyrrolidinyl) -2 -butynyl group, 3- (1-pyrrolidinyl) -1-pentinyl group, 4- (1-pyrrolidinyl) -1-pentinyl group, 5- (1-pyrrolidinyl) -1-pentinyl group, 4- (1-pyrrolidinyl) -2-pentinyl group, 5- (1-pyrrolidinyl) -2-pentinyl group, 5- (1-pyrrolidinyl) -3-pentinyl group, 3- (1-piperidinyl) -1-propynyl group, 3- (1- piperidinyl) -1-butynyl group, 4- (1-piperidinyl) -1-butynyl group, 4- (1-piperidinyl) -2-butynyl group, 3 - (1-piperidinyl) -1-pentinyl group, 4- (1-piperidinyl) -1-pentinyl group, 5- (1-piperidinyl) -1-pentinyl group, 4- (1-piperidinyl) -2-pentinyl group 5- (1-piperidinyl) -2-pentinyl group, 5- (1-piperidinyl) -3-pentinyl group, 3- (1-morpholinyl) -1-propynyl group, 3- (1-morpholinyl) -1- butynyl group, 4- (1-morpholinyl) -1-butynyl group, 4- (1-morpholinyl) -2-butynyl group, 3- (1-morpholinyl) -1-pentinyl group, 4- (1-morpholinyl) - 1-pentinyl group, 5- (1-morpholinyl) -1-pentinyl group, 4- (1-morpholinyl) -2-pentinyl group, 5- (1-morpholinyl) -2-pentini l-group, 5- (1-morpholinyl) -3-pentinyl group, 3-methoxycarbonyl-1-propynyl group, 3-methoxycarbonyl-1-butynyl group, 4-methoxycarbonyl-1-butynyl group, 4-methoxycarbonyl-2-butynyl group, 3-methoxycarbonyl-1-pentinyl group, 4-methoxycarbonyl-1-pentinyl group, 5-methoxycarbonyl-1-pentinyl group, 4-methoxycarbonyl-2-pentinyl group, 5-methoxycarbonyl-2-pentinyl group, 5-methoxycarbonyl -3-pentinyl group, 3-dimethylaminocarbonyl-1-propynyl group, 3-dimethylamino-carbonyl-1-butynyl group, 4-di methylaminocarbonyl-1-butynyl group, 4-dimethylaminocarbonyl-2-butynyl group, 3-dimethylaminocarbonyl-1-pentinyl group, 4-dimethylamino-carbonyl-1-pentinyl group, 5-dimethylamino-carbonyl-1-pentinyl group, 4-dimethylamine -2-pentinyl group, 5-dimethylaminocarbonyl-2-pentinyl group, 5-dimethylaminocarbonyl-3-pentinyl group, 3- (1-pyrrolidinyl) carbonyl-1-propynyl group, 3- (1-pyrrolidinyl) carbonyl-1-butynyl group, 4- (1-pyrrolidinyl) carbonyl-1-butynyl group, 4- (1-pyrrolidinyl) carbonyl-2-butynyl gr uppa, 3- (1-pyrrolidinyl) carbonyl-1-pentinyl group, 4- (1-pyrrolidinyl) carbonyl-1-pentinyl group, 5- (1-pyrrolidinyl) carbonyl-1-pentinyl group, 4- (1-pyrrolidinyl ) carbonyl-2-pentinyl group, 5- (1-pyrrolidinyl) carbonyl-2-pentinyl group, 5- (1-pyrrolidinyl) carbonyl-3-pentinyl group, 3- (1-piperidinyl) carbonyl-1-propynyl group, 3- (1-piperidinyl) carbonyl-1-butynyl group, 4- (1-piperidinyl) carbonyl-1-butynyl group, 4- (1-piperidinyl) carbonyl-2-butynyl group, 3- (1-piperidinyl) carbonyl -1-pentinyl group, 4- (1-piperidinyl) carbo nyl-1-pentinyl group, 5- (1-piperidinyl) carbonyl-1-pentinyl group, 4- (1-piperidinyl) carbonyl-2-pentinyl group, 5- (1-piperidinyl) carbonyl-2-pentinyl group, 5 - (1-piperidinyl) carbonyl-3-pentinyl group, 3- (1-morpholinyl) carbonyl-1-propynyl group, 3- (1-morpholinyl) carbonyl-1-butynyl group, 4- (1-morpholinyl) carbonyl- 1-butynyl group, 4- (1-morpholinyl) carbonyl-2-butynyl group, 3- (1-morpholinyl) carbonyl-1-pentinyl group, 4- (1-morpholinyl) carbonyl-1-pentinyl group, 5- ( 1-morpholinyl) carbonyl-1-pentinyl group, 4- (1-morpholinyl) carbonyl-2-pentinyl group, 5- (1-morpholinyl) carbonyl-2-pentinyl group, 5- (1-morpholinyl) carbonyl-3-pentinyl group, 3-carboxy-1-propynyl group, 3-carboxy-1- butynyl group, 4-carboxy-1-butynyl group, 4-carboxy-2-butynyl group, 3-carboxy-1-pentinyl group, 4-carboxy-1-pentinyl group, 5-carboxy-1-pentinyl group, 4- carboxy-2-pentinyl group, 5-carboxy-2-pentinyl group, 5-carboxy-3-pentinyl group, 3-acetoxy-1-propynyl group, 3-acetoxy-1-butynyl group, 4-acetoxy-1-butynyl group 4 cetoxy-2-butynyl group, 3-acetoxy-1-pentinyl group, 4-acetoxy-1-pentinyl group, 5-acetoxy-1-pentinyl group, 4-acetoxy-2-pentinyl group, 5-acetoxy-2-pentinyl group, 5-acetoxy-3-pentynyl group, 3-methoxycarbonyloxy-1-propynyl group, 3-methoxycarbonyloxy-1-butynyl group, 4-methoxycarbonyloxy-1-butynyl group, 4-methoxycarbonyloxy-2-butynyl group, 3-methoxycarbonyloxy -1-pentinyl group, 4-methoxycarbonyloxy-1-pentinyl group, 5-methoxycarbonyloxy-1-pentinyl group, 4-methoxy arbonyloxy-2-pentynyl group, 5-methoxycarbonyloxy-2-pentinyl group, 5-methoxycarbonyloxy-3-pentinyl group, 2-bromoethyl group, 2-iodoethynyl group, 3-fluoro-1-propynyl group, 3,3-difluoro- 1-propynyl group, 3,3,3-tridifluoro-1-propynyl group, 3-fluoro-1-propynyl group, 3,3-difluoro-1-propynyl group, 3,3,3-trifluoro-1-propynyl group , 1-fluoro-2-propynyl group, 1,1-difluoro-2-propynyl group, 3-fluoro-1-butynyl group, 4-fluoro-1-butynyl group, 3-fluoro-1-pentinyl group, 4- fluoro-1-pentinyl group, 5-fluoro-1-pent nilnaya group, ethynyl group, 1-propynyl group, a 2-propynyl group, a 1-butynyl group, 2-butynyl, 3-butynyl group, 1-pentynyl group, 2-pentynyl, 3-pentynyl group and the like groups.

Examples of the “C3-C6 cycloalkyl group optionally substituted with a halogen atom” in the E1 group include a cyclopropyl group.

Examples of the group represented by the “-OR ⁶ ” group in the E1 group include a C1-C4 alkoxy group optionally substituted with a halogen atom such as a 2-propynyloxy group, a 2-butynyloxy group and other similar groups; A C3-C6 alkenyloxy group optionally substituted with a halogen atom; and a C3-C6 alkynyloxy group optionally substituted with a halogen atom.

Examples of the group represented by the “-SR ⁶ ” group in the E1 group include a C1-C4 alkylthio group optionally substituted with a halogen atom.

Examples of the group represented by the group “—S (═O) R ⁶ ” in the group E1 include a C1-C4 alkylsulfinyl group optionally substituted with a halogen atom.

Examples of the group represented by the group “—S (═O) ₂ R ⁶ ” in the group E1 include a C1-C4 alkylsulfonyl group optionally substituted with a halogen atom.

Examples of the group represented by the group “—C (═O) R ⁷ ” in the group E1 include a group in which R ⁷ is a C1-C4 alkyl group optionally substituted with a halogen atom; a group in which R ⁷ is a C1-C4 alkoxy group optionally substituted with a halogen atom; a group in which R ⁷ is a C3-C6 alkenyloxy group optionally substituted with a halogen atom; a group in which R ⁷ is a C3-C6 alkynyloxy group optionally substituted with a halogen atom; a group in which R ⁷ is an amino group, a C1-C4 alkylamino group optionally substituted with a halogen atom, or a di (C1-C4 alkyl) amino group optionally substituted with a halogen atom; a group in which R ⁷ is a C 2 -C 5 cyclic amino group; a group in which R ⁷ is a hydroxyl group; and a group in which R ⁷ is a hydrogen atom.

Examples of the group represented by the group “—OC (═O) R ⁸ ” in the group E1 include a group in which R ⁸ is a C1-C4 alkyl group optionally substituted with a halogen atom; a group in which R ⁸ is a C1-C4 alkoxy group optionally substituted with a halogen atom; a group in which R ⁸ is a C3-C6 alkenyloxy group optionally substituted with a halogen atom; a group in which R ⁸ is a C3-C6 alkynyloxy group optionally substituted with a halogen atom; a group in which R ⁸ is an amino group, a C1-C4 alkylamino group optionally substituted with a halogen atom, or a di (C1-C4 alkyl) amino group optionally substituted with a halogen atom; a group in which R ⁸ is a C 2 -C 5 cyclic amino group; and a group in which R ⁸ is a hydrogen atom.

In group E2, examples of “= NO-R ⁶ ” include a methoxyimino group, an ethoxyimino group, an isopropoxyimino group, a cyclopropylimino group, a 2,2,2-trifluoroethoxyimino group, an allylimino group, and a 3-propynylimino group.

Examples of “= C (R ¹¹ R ¹² )” in the E2 group include a methylidene group, an ethylidene group, a 1-methylethylidene group, a propylidene group, and a dichloromethylidene group.

In group E3, examples of a “C2-C6 alkylene group optionally substituted with a group selected from group L” include an ethane-1,2-diyl group, a propane-1,2-diyl group, a propane-1,3-diyl group, butane A -1,4-diyl group, a 2,3-dichlorobutane-1,4-diyl group, and a pentane-1,5-diyl group.

In group E3, examples of a “C4-C6 alkenylene group optionally substituted with a group selected from group L” include a 2-butene-1,4-diyl group and a 3-penten-1,5-diyl group. Examples of the group represented by “GT ¹ —G—” in the E3 group include —OCH ₂ O—, —SCH ₂ S—, —OCH ₂ CH ₂ O— and —SCH ₂ CH ₂ S—.

Examples of the group represented by "-GT ¹ -GT ² -" in the E3 group include -OCH ₂ OCH ₂ -, -SCH ₂ SCH ₂ -, -OCH ₂ CH ₂ OCH ₂ - and -SCH ₂ CH ₂ SCH ₂ -.

Examples of the “C1-C5 haloalkyl group containing at least one fluorine atom” include a C1-C5 alkyl group substituted only with a fluorine atom (fluorine atoms) such as a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, 1,1,2,2, 2-pentafluoroethyl group, 2,2,2-trifluoroethyl group, 1,1-difluoroethyl group, 1,1,2,2,3,3,3-heptafluoropropyl group, 1,1-difluoropropyl group, 2,2-difluoropropyl group, 3,3,3-trifluoropropyl group, 1,1,2,2,3,3,4,4,4,4-nonafluorobutyl group, 1,1-difluorobutyl group, 2,2-difluorobutyl group, 1,1, 2,2,3,3 4,4,5,5,5-undecafluoropentyl group, 1,1-difluoropentyl group, 2,2-difluoropentyl group and other similar groups; A C1-C5 alkyl group substituted with a fluorine atom (fluorine atoms) and a chlorine atom (chlorine atoms), such as a chlorodifluoromethyl group, a 1,2-dichloro-1,2,2-trifluoroethyl group, 1,1-dichloro-2,2 , 2-trifluoroethyl group, 1-chloro-1,3,3,3-tetrafluoropropyl group, 2,3-dichloro-2,3,3-trifluoropropyl group, 2,2-dichloro-3,3,3-trifluoropropyl group and other similar groups; and a C1-C5 alkyl group substituted with a fluorine atom (fluorine atoms) and a bromine atom (bromine atoms), such as a 2,2-dibromo-3,3,3-trifluoropropyl group, 2-bromo-3,3,3-trifluoropropyl group, 2,3-dibromo-3,3-difluoropropyl group, 3-bromo-3,3-difluoropropyl group, 1-bromo-1,3,3,3-tetrafluoropropyl group, 1-bromo-2,2,3 , 3,3-pentafluoropropyl group, 1,3-dibromo-2,2,3,3-tetrafluoropropyl group, 3-bromo-2,3,3-trifluoropropyl group, 3-bromo-2,2,3,3- tetrafluoropropyl group, 2,3-dibromo-2,3,3-trifluoropropyl group, 3-bromo-3,3-difluoropropyl group and other similar groups.

Examples of the “C1-C3 haloalkyl group containing at least one fluorine atom” include a C1-C3 alkyl group substituted only by a fluorine atom (fluorine atoms) such as a trifluoromethyl group, 1,1,2,2,2-pentafluoroethyl group, 1 , 1-difluoroethyl group, 1,1,2,2,3,3,3-heptafluoropropyl group and other similar groups; A C1-C3 alkyl group substituted with a fluorine atom (fluorine atoms) and a chlorine atom (chlorine atoms), such as a chlorodifluoromethyl group, a 1,2-dichloro-1,2,2-trifluoroethyl group, 1,1-dichloro-2,2, A 2-trifluoroethyl group, 1-chloro-1,3,3,3-tetrafluoropropyl group, 2,3-dichloro-2,3,3-trifluoropropyl group, 2,2-dichloro-3,3,3-trifluoropropyl group and other similar groups; and a C1-C3 alkyl group substituted with a fluorine atom (fluorine atoms) and a bromine atom (bromine atoms), such as a 2,2-dibromo-3,3,3-trifluoropropyl group, a 2-bromo-3,3,3-trifluoropropyl group , 2,3-dibromo-3,3-difluoropropyl group, 3-bromo-3,3-difluoropropyl group, 1-bromo-1,3,3,3-tetrafluoropropyl group, 1-bromo-2,2,3, 3,3-pentafluoropropyl group, 1,3-dibromo-2,2,3,3-tetrafluoropropyl group, 3-bromo-2,3,3-trifluoropropyl group, 3-bromo-2,2,3,3-tetrafluoropropyl a group, 2,3-dibromo-2,3,3-trifluoropropyl group, 3-bromo-3,3-difluoropropyl group and other similar groups.

Examples of the “C1-C5 fluoroalkyl group” include a fluoromethyl group, a trifluoromethyl group, a 1,1,2,2,2-pentafluoroethyl group, a 2,2,2-trifluoroethyl group, a 1,1-difluoroethyl group, 1,1,2,2 , 3,3,3-heptafluoropropyl group, 1,1-difluoropropyl group, 2,2-difluoropropyl group, 3,3,3-trifluoropropyl group, 1,1,2,2,3,3,4,4,4,4 non-fluorobutyl group, 1,1-difluorobutyl group, 2,2-difluorobutyl group, 1,1,2,2,3,3,4,4,5,5,5,5-undecafluoropentyl group, 1,1-difluoropentyl group and 2,2-difluoropentyl group.

Examples of the “C1-C3 fluoroalkyl group” include a fluoromethyl group, a trifluoromethyl group, a 1,1,2,2,2-pentafluoroethyl group, a 1,1-difluoroethyl group and a 1,1,2,2,3,3,3-heptafluoropropyl group .

Examples of a “halogen atom” include a fluorine atom, a chlorine atom, and a bromine atom.

Examples of a “C1-C4 optionally substituted halogen atom hydrocarbon group” include a C1-C4 alkyl group optionally substituted by a halogen atom, a C2-C4 alkenyl group optionally substituted by a halogen atom, and a C2-C4 alkynyl group optionally substituted by a halogen atom.

Examples of the “C1-C4 alkyl group optionally substituted by a halogen atom” include a methyl group, an ethyl group, a propyl group, a 1-methylethyl group (hereinafter, in some cases referred to as an isopropyl group), a 2,2-dimethylpropyl group, a chloromethyl group, fluoromethyl group, difluoromethyl group, trifluoromethyl group, 2,2,2-trifluoromethyl group, 1,1,2,2-tetrafluoroethyl group, 1,1,2,2,2-pentafluoroethyl group and 1,1-dimethylethyl group (hereinafter in this description in some cases called tert-butyl g uppoy).

Examples of the “C2-C4 alkenyl group optionally substituted with a halogen atom” include a vinyl group, a 2,2-difluorovinyl group, a 1,2,2-trifluorovinyl group, a 1-propenyl group, a 2-propenyl group, 3,3-difluoro-2 a propenyl group, a 1-methyl-2-propenyl group, a 2-methyl-2-propenyl group, a 1-butenyl group and a 2-butenyl group.

Examples of the “C2-C4 alkynyl group optionally substituted with a halogen atom” include an ethynyl group, a 1-propynyl group, a 3.3,3-trifluoro-1-propynyl group, a 2-propynyl group, a 1-methyl-2-propynyl group, 1 -butynyl group, 2-butynyl group and 3-butynyl group.

Examples of the “C1-C4 alkoxy group optionally substituted with a halogen atom” include a methoxy group, an ethoxy group, a propoxy group, a trifluoromethoxy group, a bromodifluoromethoxy group, a difluoromethoxy group, a chlorodifluoromethoxy group, a pentafluoroethoxy group, 2,2,2-trifluoroethuoro-fluoro-fluorine.

Examples of the “C3-C6 alkenyloxy group optionally substituted by a halogen atom” include a 1-propenyloxy group, 2-propenyloxy group, 1-methyl-2-propenyloxy group, 1,1-dimethyl-2-propenyloxy group and 2,2-difluoro-2-propenyloxy group.

Examples of the “C3-C6 alkynyloxy group optionally substituted with a halogen atom” include a 2-propynyloxy group, 1-methyl-2-propynyloxy group, 1,1-dimethyl-2-propynyloxy group, 2-butynyloxy group, 1-methyl-2-butynyloxy group, 1,1 a dimethyl-2-butynyloxy group and a 3.3,3-trifluoro-1-propynyloxy group.

Examples of a “C1-C4 alkylamino group optionally substituted with a halogen atom” include an N-methylamino group, an N-ethylamino group, an N-propylamino group, an N- (1-methylethyl) amino group, and an N- (2,2,2-trifluoroethyl) amino group.

Examples of the “di (C1-C4 alkyl) amino group optionally substituted with a halogen atom” include N, N-dimethylamino group, N-ethyl-N-methylamino group, N, N-diethylamino group, N-methyl-N-propylamino group, N-ethyl-N propylamino group, N, N-dipropylamino group, N-methyl-N- (1-methylethyl) amino group, N-ethyl-N- (1-methylethyl) amino group, N, N-di (1-methylethyl) amino group, N-methyl An -N- (2,2,2-trifluoroethyl) amino group; and an N-methyl-N-ethyl-N- (2,2,2-trifluoroethyl) amino group.

Examples of the “C2-C5 cyclic amino group” include a 1-aziridine group, a 1-azetidinyl group, a 1-pyrrolidinyl group, a piperidine group, and a morpholine group.

Examples of a “hydrocarbon group with a C1-C6 chain optionally substituted with a group selected from L” include a C1-C6 alkyl group optionally substituted with a group selected from L, a C2-C6 alkenyl group optionally substituted with a group selected from L, and C2-C6 alkynyl group optionally substituted with a group selected from L.

Examples of the “C1-C6 alkyl group optionally substituted with a group selected from the group L” include a C1-C6 alkyl group optionally substituted with a halogen atom such as a methyl group, an ethyl group, a propyl group, a 1-methylethyl group, a 2,2-dimethylpropyl group , chloromethyl group, fluoromethyl group, difluoromethyl group, trifluoromethyl group, 2,2,2-trifluoroethyl group, 1,1,2,2-tetrafluoroethyl group, 1,1,2,2,2-pentafluoroethyl group, 1,1- dimethylethyl group and other similar groups; A (C1-C4 alkoxy) C1-C4 alkyl group optionally substituted with a halogen atom such as a methoxymethyl group, an ethoxymethyl group, a 1-methoxyethyl group, a 1-ethoxyethyl group, a trifluoromethoxymethyl group and other similar groups; A (C3-C6 alkenyloxy) C1-C4 alkyl group optionally substituted with a halogen atom such as a (1-propenyloxy) methyl group, (2-propenyloxy) methyl group, (1-methyl-2-propenyloxy) methyl group, (1,1- dimethyl-2-propenyloxy) methyl group, (2,2-difluoro-2-propenyloxy) methyl group, 1- (1-propenyloxy) ethyl group, 1- (2-propenyloxy) ethyl group, 1- (1-methyl- 2-propenyloxy) ethyl group, 1- (1,1-dimethyl-2-propenyloxy) ethyl group, 1- (2,2-difluoro-2-propenyloxy) ethyl group, 2- (1-propenyloxy) ethyl group, 2 - (2-propenyloxy) ethyl group, 2- (1- etil-2-propenyloxy) ethyl group, 2- (1,1-dimethyl-2-propenyloxy) ethyl group and 2- (2,2-Difluoro-2-propenyloxy) ethyl group; A (C3-C6 alkynyloxy) C1-C4 alkyl group optionally substituted with a halogen atom such as a (2-propynyloxy) methyl group, (1-methyl-2-propynyloxy) methyl group, (1,1-dimethyl-2-propynyloxy) methyl group , (2-butynyloxy) methyl group, (1-methyl-2-butynyloxy) methyl group, (1,1-dimethyl-2-butynyloxy) methyl group, (3,3,3-trifluoro-1-propynyloxy) methyl group , 1- (2-propynyloxy) ethyl group, 1- (1-methyl-2-propynyloxy) ethyl group, 1- (1,1-dimethyl-2-propynyloxy) ethyl group, 1- (2-butynyloxy) ethyl group , 1- (1-methyl-2-butynyloxy) ethyl group, 1- (1,1-dimethyl-2-butynyloxy) ethyl group, 1- (3,3,3-trifluoro-1-propynyloxy) ethyl group, 2- (2-propynyloxy) ethyl group, 2- (1 -methyl-2-propynyloxy) ethyl group, 2- (1,1-dimethyl-2-propynyloxy) ethyl group, 2- (2-butynyloxy) ethyl group, 2- (1-methyl-2-butynyloxy) ethyl group, 2- (1,1-dimethyl-2-butynyloxy) ethyl group, 2- (3,3,3-trifluoro-1-propynyloxy) ethyl group and other similar groups; and a (hydroxy) C1-C4 alkyl group optionally substituted with a halogen atom such as a hydroxymethyl group, a 1-hydroxyethyl group, a 1-hydroxy-1-methylethyl group, a 2-hydroxyethyl group, a 2-hydroxy-1-methylethyl group, and other similar groups .

Examples of the “C2-C6 alkenyl group optionally substituted with a group selected from group L” include a C2-C6 alkenyl group optionally substituted with a halogen atom such as a vinyl group, a 2,2-difluorovinyl group, a 1,2,2-trifluorovinyl group, 1 -propenyl group, 2-propenyl group, 3,3-difluoro-2-propenyl group, 1-methyl-2-propenyl group and other similar groups.

Examples of the “C2-C6 alkynyl group optionally substituted with a group selected from group L” include an ethynyl group such as a 1-ethynyl group, 2-bromoethynyl group, 2-iodo-ethynyl group, 2- (methoxycarbonyl) ethynyl group and the like. groups 1-propynyl group such as 1-propynyl group, 3-fluoro-1-propynyl group, 3,3-difluoro-1-propynyl group, 3- (dimethylamino) -1-propynyl group, 3,3,3-trifluoro A -1-propynyl group, a 3-methoxy-1-propynyl group, a 3- (methoxycarbonyl) -1-propynyl group and other similar groups; A 2-propynyl group such as a 2-propynyl group, a 1-fluoro-2-propynyl group, a 1,1-difluoro-2-propynyl group; 1-butynyl group such as 1-butynyl group, 4-fluoro-1-butynyl group, 4-methoxy-1-butynyl group, 4- (dimethylamino) -1-butynyl group, 4- (methoxycarbonyl) -1-butynyl a group and other similar groups; 2-butynyl group such as 2-butynyl group, 4-fluoro-2-butynyl group, 4-methoxy-2-butynyl group, 4- (dimethylamino) -2-butynyl group, 4- (methoxycarbonyl) -2-butynyl a group and other similar groups; A 3-butynyl group such as a 3-butynyl group, a 1,1-difluoro-3-butynyl group and the like; 1-pentinyl group such as 1-pentinyl group, 5-fluoro-1-pentinyl group, 5-methoxy-1-pentinyl group, 5- (dimethylamino) -1-pentinyl group, 5- (methoxycarbonyl) -1-pentinyl a group and other similar groups; and a 2-pentinyl group such as a 2-pentinyl group, a 5-fluoro-2-pentinyl group, a 5-methoxy-2-pentinyl group, a 5- (dimethylamino) -2-pentinyl group, 5- (methoxycarbonyl) -2- pentinyl group and other similar groups.

Examples of the “C3-C6 cycloalkyl group optionally substituted with a halogen atom” include a cyclopropyl group, 1-methylcyclopropyl group, 2,2-dichlorocyclopropyl group, 2,2-dichloro-1-methylcyclopropyl group, 2,2-difluorocyclopropyl group, 2,2 a difluoro-1-methylcyclopropyl group, a cyclobutyl group, a cyclopentyl group and a cyclohexyl group.

Examples of the “phenyl group optionally substituted by a halogen atom” include a phenyl group, a 2-chlorophenyl group, a 3-chlorophenyl group, a 4-chlorophenyl group, a 2,3-dichlorophenyl group, a 2,4-dichlorophenyl group, a 2,5-dichlorophenyl group , 2,6-dichlorophenyl group, 3,4-dichlorophenyl group, 3,5-dichlorophenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2,3-difluorophenyl group, 2,4-difluorophenyl group , 2,5-difluorophenyl group, 2,6-difluorophenyl group, 3,4-difluorophenyl group, 3,5-difluorophene ln group, 2-bromophenyl group, 3-bromophenyl group, 4-bromophenyl group, 2,3-dibromophenyl group, 2,4-dibromophenyl group, 2,5-dibromophenyl group, 2,6-dibromophenyl group, 3,4- dibromophenyl group; and 3,5-dibromophenyl group.

Specific examples of the compounds of the present invention include:

the compound represented by formula (I), where m is 0;

the compound represented by formula (I), where m is 1;

the compound represented by formula (I), where m is equal to 2;

the compound represented by formula (I), where n is 0;

the compound represented by formula (I), where n is 1;

the compound represented by formula (I), where n is 2;

the compound represented by formula (I), where R ¹ is a hydrogen atom;

the compound represented by formula (I), where R ¹ is a C1-C4 alkyl group optionally substituted with a halogen atom;

the compound represented by formula (I), where R ¹ is a methyl group;

the compound represented by formula (I), where R ¹ is a C2-C4 alkenyl group optionally substituted with a halogen atom;

the compound represented by formula (I), where R ¹ is a C2-C4 alkynyl group optionally substituted with a halogen atom;

the compound represented by formula (I), where R ¹ is a halogen atom;

the compound represented by formula (I), where R ¹ is a fluorine atom;

the compound represented by formula (I), where R ¹ is a chlorine atom;

the compound represented by formula (I), where R ¹ is a bromine atom;

the compound represented by formula (I), where R ² is a hydrogen atom;

the compound represented by formula (I), where R ² is a C1-C4 alkyl group optionally substituted by a halogen atom;

the compound represented by formula (I), where R ² is a group-C (= O) R ⁵ and R ⁵ is a C1-C4 alkyl group optionally substituted by a halogen atom;

the compound represented by formula (I), where R ² is a group -C (= O) R ⁵ and R ⁵ is a C1-C4 alkoxy group optionally substituted with a halogen atom;

the compound represented by formula (I), where R ² is a methoxycarbonyl group;

the compound represented by formula (I), where R ² is a group -C (= O) R ⁵ and R ⁵ is a C3-C6 alkenyloxy group optionally substituted with a halogen atom;

the compound represented by formula (I), where R ² is a group -C (= O) R ⁵ and R ⁵ is a C3-C6 alkynyloxy group optionally substituted with a halogen atom;

the compound represented by formula (I), where R ² is a group -C (= O) R ⁵ and R ⁵ is an amino group, a C1-C4 alkylamino group optionally substituted by a halogen atom, or a di (C1-C4 alkyl) amino group optionally substituted by a halogen atom ;

the compound represented by formula (I), where R ² is a group -C (= O) R ⁵ and R ⁵ is a C2-C5 cyclic amino group;

the compound represented by formula (I), where R ² is a group -C (= O) NH ₂ ;

the compound represented by formula (I), where R ² is a group -C (= O) OH;

the compound represented by formula (I), where R ² is a group -C (= O) H;

the compound represented by formula (I), where R ² is a group-C (= S) R ⁵ and R ⁵ is a C1-C4 alkyl group optionally substituted by a halogen atom;

the compound represented by formula (I), where R ² is a group -C (= S) R ⁵ and R ⁵ is a C1-C4 alkoxy group optionally substituted with a halogen atom;

the compound represented by formula (I), where R ² is a group -C (= S) R ⁵ and R ⁵ is a C3-C6 alkenyloxy group optionally substituted with a halogen atom;

the compound represented by formula (I), where R ² is a group -C (= S) R ⁵ and R ⁵ is a C3-C6 alkynyloxy group optionally substituted with a halogen atom;

the compound represented by formula (I), where R ² is a group -C (= S) R ⁵ and R ⁵ is a C1-C4 alkylamino group optionally substituted by a halogen atom, or a di (C1-C4alkyl) amino group optionally substituted by a halogen atom;

the compound represented by formula (I), where R ² is a group -C (= S) R ⁵ and R ⁵ is a C2-C5 cyclic amino group;

the compound represented by formula (I), where R ² is a group -C (= S) NH ₂ ;

the compound represented by formula (I), where R ² is a group -C (= S) OH, and R ⁵ is a hydroxyl group;

the compound represented by formula (I), where R ² is a group -C (= S) H;

the compound represented by formula (I), where R ² is a cyano group;

the compound represented by formula (I), where R ² is a halogen atom;

the compound represented by formula (I), where R ¹ and R ² are hydrogen atoms;

the compound represented by formula (I), where Q is a C1-C3 haloalkyl group containing at least one fluorine atom;

the compound represented by formula (I), where Q is a C1-C5 fluoroalkyl group;

the compound represented by formula (I), where Q is a fluorine atom;

the compound represented by formula (I), where Q is a C1-C3 fluoroalkyl group;

the compound represented by formula (I), where Q is a fluoromethyl group;

the compound represented by formula (I), where Q is a trifluoromethyl group;

the compound represented by formula (I), where Q is a 2,2,2-trifluoroethyl group;

the compound represented by formula (I), where Q is a 1,1,2,2,2-pentafluoroethyl group;

the compound represented by formula (I), where A is a C3-C7 cycloalkyl group, optionally substituted by a group selected from the groups E1-E3;

the compound represented by formula (I), where A is a cyclopropyl group, optionally substituted by a group selected from the groups E1-E3;

the compound represented by formula (I), where A is a cyclopentyl group, optionally substituted by a group selected from groups E1-E3;

the compound represented by formula (I), where A is a cyclohexyl group, an optionally substituted group selected from groups E1-E3;

the compound represented by formula (I), where A is a cycloheptyl group, an optionally substituted group selected from the groups E1-E3;

the compound represented by formula (I), where A is a C5-C7 cycloalkenyl group, an optionally substituted group selected from the groups E1-E3;

the compound represented by formula (I), where A is a 1-cyclopentenyl group, an optionally substituted group selected from the groups E1-E3;

the compound represented by formula (I), where A is a 2-cyclopentenyl group, an optionally substituted group selected from the groups E1-E3;

the compound represented by formula (I), where A is a 3-cyclopentenyl group, an optionally substituted group selected from the groups E1-E3;

the compound represented by formula (I), where A is a 1-cyclohexenyl group, an optionally substituted group selected from the groups E1-E3;

the compound represented by formula (I), where A is a 2-cyclohexenyl group, an optionally substituted group selected from the groups E1-E3;

the compound represented by formula (I), where A is a 3-cyclohexenyl group, an optionally substituted group selected from the groups E1-E3;

the compound represented by formula (I), where A is a 1-cycloheptenyl group, an optionally substituted group selected from the groups E1-E3;

the compound represented by formula (I), where A is a 2-cycloheptenyl group, optionally substituted by a group selected from the groups E1-E3;

the compound represented by formula (I), where A is a 3-cycloheptenyl group, an optionally substituted group selected from the groups E1-E3;

the compound represented by formula (I), where A is a 4-cycloheptenyl group, an optionally substituted group selected from the groups E1-E3;

the compound represented by formula (I), where A is a cyclopentyl group, an optionally substituted group selected from groups E1-E3, at position 3;

the compound represented by formula (I), where A is a cyclopentyl group optionally substituted with two groups selected from groups E1-E3 at position 3;

the compound represented by formula (I), where A is a cyclopentyl group, position 2 and position 3 of which, each optionally substituted by a group selected from groups E1-E3;

the compound represented by formula (I), where A is a cyclopentyl group, position 3 and position 4 of which, each optionally substituted by a group selected from groups E1-E3;

the compound represented by formula (I), where A is a cyclohexyl group, an optionally substituted group selected from groups E1-E3, at position 3;

the compound represented by formula (I), where A is a cyclohexyl group optionally substituted with two groups selected from groups E1-E3 at position 3;

the compound represented by formula (I), where A is a cyclohexyl group, an optionally substituted group selected from groups E1-E3 at position 4;

the compound represented by formula (I), where A is a cyclohexyl group optionally substituted with two groups selected from groups E1-E3 at position 4;

the compound represented by formula (I), where A is a cyclohexyl group, position 2 and position 3 of which, each is optionally substituted with a group selected from groups E1-E3;

the compound represented by formula (I), where A is a cyclohexyl group, position 2 and position 4 of which, each is optionally substituted with a group selected from the groups E1-E3;

the compound represented by formula (I), where A is a cyclohexyl group, position 3 and position 4 of which, each is optionally substituted with a group selected from groups E1-E3;

the compound represented by formula (I), where A is a 1-cyclopentenyl group, an optionally substituted group selected from the groups E1-E3, at position 3;

the compound represented by formula (I), where A is a 1-cyclopentenyl group, an optionally substituted group selected from groups E1-E3, at position 4;

the compound represented by formula (I), where A is a 1-cyclopentenyl group optionally substituted by two groups selected from groups E1-E3 at position 3;

the compound represented by formula (I), where A is a 1-cyclopentenyl group optionally substituted by two groups selected from groups E1-E3, at position 4;

the compound represented by formula (I), where A is a 1-cyclopentenyl group, position 3 and position 4 of which, each is optionally substituted with a group selected from groups E1-E3;

the compound represented by formula (I), where A is a 2-cyclopentenyl group, an optionally substituted group selected from the groups E1-E3, at position 3;

the compound represented by formula (I), where A is a 2-cyclopentenyl group, an optionally substituted group selected from the groups E1-E3, at position 4;

the compound represented by formula (I), where A is a 2-cyclopentenyl group, optionally substituted with two groups selected from groups E1-E3, at position 4;

the compound represented by formula (I), where A is a 2-cyclopentenyl group, position 3 and position 4 of which, each is optionally substituted with a group selected from groups E1-E3;

the compound represented by formula (I), where A is a 3-cyclopentenyl group, an optionally substituted group selected from the groups E1-E3, at position 3;

the compound represented by formula (I), where A is a 3-cyclopentenyl group, an optionally substituted group selected from the groups E1-E3, at position 4;

the compound represented by formula (I), where A is a 3-cyclopentenyl group, position 3 and position 4 of which, each is optionally substituted with a group selected from groups E1-E3;

the compound represented by formula (I), where A is a 1-cyclohexenyl group, an optionally substituted group selected from the groups E1-E3, at position 3;

the compound represented by formula (I), where A is a 1-cyclohexenyl group, an optionally substituted group selected from the groups E1-E3, at position 4;

the compound represented by formula (I), where A is a 1-cyclohexenyl group, an optionally substituted group selected from the groups E1-E3, at position 5;

the compound represented by formula (I), where A is a 1-cyclohexenyl group, optionally substituted by two groups selected from groups E1-E3, at position 3;

the compound represented by formula (I), where A is a 1-cyclohexenyl group optionally substituted with two groups selected from groups E1-E3 at position 4;

the compound represented by formula (I), where A is a 1-cyclohexenyl group, optionally substituted by two groups selected from groups E1-E3, at position 5;

the compound represented by formula (I), where A is a 1-cyclohexenyl group, position 2 and position 3 of which, each is optionally substituted with a group selected from groups E1-E3;

the compound represented by formula (I), where A is a 1-cyclohexenyl group, position 2 and position 4 of which, each is optionally substituted with a group selected from groups E1-E3;

the compound represented by formula (I), where A is a 1-cyclohexenyl group, position 2 and position 5 of which, each is optionally substituted with a group selected from the groups E1-E3;

the compound represented by formula (I), where A is a 1-cyclohexenyl group, position 3 and position 4 of which, each is optionally substituted with a group selected from groups E1-E3;

the compound represented by formula (I), where A is a 1-cyclohexenyl group, position 3 and position 5 of which, each is optionally substituted with a group selected from groups E1-E3;

the compound represented by formula (I), where A is a 1-cyclohexenyl group, position 3 and position 6 of which, each is optionally substituted with a group selected from the groups E1-E3;

the compound represented by formula (I), where A is a 1-cyclohexenyl group, position 4 and position 5 of which, each is optionally substituted with a group selected from groups E1-E3;

the compound represented by formula (I), where A is a 1-cyclohexenyl group, position 4 and position 6 of which, each is optionally substituted with a group selected from groups E1-E3;

the compound represented by formula (I), where A is a 1-cyclohexenyl group, position 5 and position 6 of which, each is optionally substituted with a group selected from groups E1-E3;

the compound represented by formula (I), where A is a 2-cyclohexenyl group, an optionally substituted group selected from the groups E1-E3, at position 3;

the compound represented by formula (I), where A is a 2-cyclohexenyl group, an optionally substituted group selected from the groups E1-E3, at position 4;

the compound represented by formula (I), where A is a 2-cyclohexenyl group, an optionally substituted group selected from the groups E1-E3, at position 5;

the compound represented by formula (I), where A is a 2-cyclohexenyl group, optionally substituted by two groups selected from groups E1-E3, at position 4;

the compound represented by formula (I), where A is a 2-cyclohexenyl group, optionally substituted by two groups selected from groups E1-E3, at position 5;

the compound represented by formula (I), where A is a 2-cyclohexenyl group, position 2 and position 3 of which, each is optionally substituted with a group selected from groups E1-E3;

the compound represented by formula (I), where A is a 2-cyclohexenyl group, position 2 and position 4 of which, each is optionally substituted with a group selected from groups E1-E3;

the compound represented by formula (I), where A is a 2-cyclohexenyl group, position 2 and position 5 of which, each is optionally substituted with a group selected from groups E1-E3;

the compound represented by formula (I), where A is a 2-cyclohexenyl group, position 3 and position 4 of which, each is optionally substituted with a group selected from groups E1-E3;

the compound represented by formula (I), where A is a 2-cyclohexenyl group, position 3 and position 5 of which, each is optionally substituted with a group selected from the groups E1-E3;

the compound represented by formula (I), where A is a 2-cyclohexenyl group, position 3 and position 6 of which, each is optionally substituted with a group selected from groups E1-E3;

the compound represented by formula (I), where A is a 2-cyclohexenyl group, position 4 and position 5 of which, each is optionally substituted with a group selected from groups E1-E3;

the compound represented by formula (I), where A is a 2-cyclohexenyl group, position 4 and position 6 of which, each is optionally substituted with a group selected from groups E1-E3;

the compound represented by formula (I), where A is a 2-cyclohexenyl group, position 5 and position 6 of which, each is optionally substituted with a group selected from groups E1-E3;

the compound represented by formula (I), where A is a 3-cyclohexenyl group, an optionally substituted group selected from the groups E1-E3, at position 3;

the compound represented by formula (I), where A is a 3-cyclohexenyl group, an optionally substituted group selected from the groups E1-E3, at position 4;

the compound represented by formula (I), where A is a 3-cyclohexenyl group, an optionally substituted group selected from the groups E1-E3, at position 5;

the compound represented by formula (I), where A is a 3-cyclohexenyl group optionally substituted with two groups selected from groups E1-E3 at position 5;

the compound represented by formula (I), where A is a 3-cyclohexenyl group, position 2 and position 3 of which, each is optionally substituted with a group selected from groups E1-E3;

the compound represented by formula (I), where A is a 3-cyclohexenyl group, position 2 and position 4 of which, each is optionally substituted with a group selected from the groups E1-E3;

the compound represented by formula (I), where A is a 3-cyclohexenyl group, position 2 and position 5 of which, each is optionally substituted with a group selected from the groups E1-E3;

the compound represented by formula (I), where A is a 3-cyclohexenyl group, position 3 and position 4 of which, each is optionally substituted with a group selected from groups E1-E3;

the compound represented by formula (I), where A is a 3-cyclohexenyl group, position 3 and position 5 of which, each is optionally substituted with a group selected from groups E1-E3;

the compound represented by formula (I), where A is a 3-cyclohexenyl group, position 3 and position 6 of which, each is optionally substituted with a group selected from groups E1-E3;

the compound represented by formula (I), where A is a 3-cyclohexenyl group, position 4 and position 5 of which, each is optionally substituted with a group selected from the groups E1-E3;

the compound represented by formula (I), where A is a 3-cyclohexenyl group, position 4 and position 6 of which, each is optionally substituted with a group selected from groups E1-E3;

the compound represented by formula (I), where A is a 3-cyclohexenyl group, position 5 and position 6 of which, each is optionally substituted with a group selected from groups E1-E3;

the compound represented by formula (I), where m is 0, and A is a 3-cyanocyclopentyl group;

the compound represented by formula (I), where m is 0, and A is a 3-fluorocyclopentyl group;

the compound represented by formula (I), where m is 0, and A is a 3,3-difluorocyclopentyl group;

the compound represented by formula (I), where m is 0, and A is a 3-ethynylcyclopentyl group;

the compound represented by formula (I), where m is 0, and A is a 3- (1-propynyl) cyclopentyl group;

the compound represented by formula (I), where m is 0, and A is a 3- (2-propynyl) cyclopentyl group;

the compound represented by formula (I), where m is 0, and A is a 3- (2-butynyl) cyclopentyl group;

the compound represented by formula (I), where m is 0, and A is a 3-methoxyiminocyclopentyl group;

the compound represented by formula (I), where m is 0, and A is a 3-ethoxyiminocyclopentyl group;

the compound represented by formula (I), where m is 0, and A is a 3-cyanocyclohexyl group;

the compound represented by formula (I), where m is 0, and A is a 3-fluorocyclohexyl group;

the compound represented by formula (I), where m is 0, and A is a 3,3-difluorocyclohexyl group;

the compound represented by formula (I), where m is 0, and A is a 3-ethynylcyclohexyl group;

the compound represented by formula (I), where m is 0, and A is 3- (1-propynyl) cyclohexyl group;

the compound represented by formula (I), where m is 0, and A is a 3- (2-propynyl) cyclohexyl group;

the compound represented by formula (I), where m is 0, and A is a 3- (2-butynyl) cyclohexyl group;

the compound represented by formula (I), where m is 0, and A is a 4-cyanocyclohexyl group;

the compound represented by formula (I), where m is 0, and A is a 3-fluoro-4-cyanocyclohexyl group;

the compound represented by formula (I), where m is 0, and A is a 4-fluoro-4-cyanocyclohexyl group;

the compound represented by formula (I), where m is 0, and A is a 4-fluorocyclohexyl group;

the compound represented by formula (I), where m is 0, and A is a 4,4-difluorocyclohexyl group;

the compound represented by formula (I), where m is 0, and A is a 4-ethynylcyclohexyl group;

the compound represented by formula (I), where m is 0, and A is a 3-fluoro-4-ethynylcyclohexyl group;

the compound represented by formula (I), where m is 0, and A is a 4-fluoro-4-ethynylcyclohexyl group;

the compound represented by formula (I), where m is 0, and A is 4- (1-propynyl) cyclohexyl group;

the compound represented by formula (I), where m is 0, and A is 4- (2-propynyl) cyclohexyl group;

the compound represented by formula (I), where m is 0, and A is 4- (1-butynyl) cyclohexyl group;

the compound represented by formula (I), where m is 0, and A is 4- (2-butynyl) cyclohexyl group;

the compound represented by formula (I), where m is 0, and A is 4- (3-methoxy-1-propinyl) cyclohexyl group;

the compound represented by formula (I), where m is 0, and A is 4- (3-methoxy-1-butynyl) cyclohexyl group;

the compound represented by formula (I), where m is 0, and A is 4- (4-methoxy-1-butynyl) cyclohexyl group;

the compound represented by formula (I), where m is 0, and A is 4- (4-methoxy-2-butynyl) cyclohexyl group;

the compound represented by formula (I), where m is 0, and A is 4- (3-methoxy-1-pentenyl) cyclohexyl group;

the compound represented by formula (I), where m is 0, and A is 4- (4-methoxy-1-pentenyl) cyclohexyl group;

the compound represented by formula (I), where m is 0, and A is 4- (5-methoxy-1-pentenyl) cyclohexyl group;

the compound represented by formula (I), where m is 0, and A is 4- (4-methoxy-2-pentenyl) cyclohexyl group;

the compound represented by formula (I), where m is 0, and A is 4- (5-methoxy-2-pentenyl) cyclohexyl group;

the compound represented by formula (I), where m is 0, and A is 4- (3-dimethylamino-1-propynyl) cyclohexyl group;

the compound represented by formula (I), where m is 0, and A is 4- (3-dimethylamino-1-butynyl) cyclohexyl group;

the compound represented by formula (I), where m is 0, and A is 4- (4-dimethylamino-1-butynyl) cyclohexyl group;

the compound represented by formula (I), where m is 0, and A is 4- (4-dimethylamino-2-butynyl) cyclohexyl group;

the compound represented by formula (I), where m is 0, and A is 4- (3-dimethylamino-1-pentenyl) cyclohexyl group;

the compound represented by formula (I), where m is 0, and A is 4- (4-dimethylamino-1-pentenyl) cyclohexyl group;

the compound represented by formula (I), where m is 0, and A is 4- (5-dimethylamino-1-pentenyl) cyclohexyl group;

the compound represented by formula (I), where m is 0, and A is 4- (4-dimethylamino-2-pentenyl) cyclohexyl group;

the compound represented by formula (I), where m is 0, and A is 4- (5-dimethylamino-2-pentenyl) cyclohexyl group;

the compound represented by formula (I), where m is 0, and A is 4- (2-methoxycarbonylethynyl) cyclohexyl group;

the compound represented by formula (I), where m is 0, and A is 4- (3-methoxycarbonyl-1-propynyl) cyclohexyl group;

the compound represented by formula (I), where m is 0, and A is 4- (3-methoxycarbonyl-1-butynyl) cyclohexyl group;

the compound represented by formula (I), where m is 0, and A is 4- (4-methoxycarbonyl-1-butynyl) cyclohexyl group;

the compound represented by formula (I), where m is 0, and A is 4- (4-methoxycarbonyl-2-butynyl) cyclohexyl group;

the compound represented by formula (I), where m is 0, and A is 4- (3-methoxycarbonyl-1-pentenyl) cyclohexyl group;

the compound represented by formula (I), where m is 0, and A is 4- (4-methoxycarbonyl-1-pentenyl) cyclohexyl group;

the compound represented by formula (I), where m is 0, and A is 4- (5-methoxycarbonyl-1-pentenyl) cyclohexyl group;

the compound represented by formula (I), where m is 0, and A is 4- (4-methoxycarbonyl-2-pentenyl) cyclohexyl group;

the compound represented by formula (I), where m is 0, and A is 4- (5-methoxycarbonyl-2-pentenyl) cyclohexyl group;

the compound represented by formula (I), where m is 0, and A is 4- (2-bromoethynyl) cyclohexyl group;

the compound represented by formula (I), where m is 0, and A is 4- (2-iodoethynyl) cyclohexyl group;

the compound represented by formula (I), where m is 0, and A is 4- (3-fluoro-1-propynyl) cyclohexyl group;

the compound represented by formula (I), where m is 0, and A is 4- (3,3-difluoro-1-propinyl) cyclohexyl group;

the compound represented by formula (I), where m is 0, and A is 4- (3,3,3-trifluoro-1-propynyl) cyclohexyl group;

the compound represented by formula (I), where m is 0, and A is 4- (1-fluoro-2-propinyl) cyclohexyl group;

the compound represented by formula (I), where m is 0, and A is 4- (1,1-difluoro-2-propinyl) cyclohexyl group;

the compound represented by formula (I), where m is 0, and A is 4- (3-fluoro-1-butynyl) cyclohexyl group;

the compound represented by formula (I), where m is 0, and A is 4- (4-fluoro-1-butynyl) cyclohexyl group;

the compound represented by formula (I), where m is 0, and A is 4- (3-fluoro-1-pentenyl) cyclohexyl group;

the compound represented by formula (I), where m is 0, and A is 4- (4-fluoro-1-pentenyl) cyclohexyl group;

the compound represented by formula (I), where m is 0, and A is 4- (5-fluoro-1-pentenyl) cyclohexyl group;

the compound represented by formula (I), where m is 0, and A is a 3-methoxyiminocyclohexyl group;

the compound represented by formula (I), where m is 0, and A is a 3-ethoxyiminocyclohexyl group;

the compound represented by formula (I), where m is 0, and A is a 4-methoxyiminocyclohexyl group;

the compound represented by formula (I), where m is 0, and A is a 4-ethoxyiminocyclohexyl group;

the compound represented by formula (I), where m is 0, and A is a 3-cyano-3-cyclopentenyl group;

the compound represented by formula (I), where m is 0, and A is a 3-fluoro-3-cyclopentenyl group;

the compound represented by formula (I), where m is 0, and A is a 3-ethynyl-3-cyclopentenyl group;

the compound represented by formula (I), where m is 0, and A is a 3- (1-propynyl) -3-cyclopentenyl group;

the compound represented by formula (I), where m is 0, and A is a 3- (2-propynyl) -3-cyclopentenyl group;

the compound represented by formula (I), where m is 0, and A is a 3- (2-butynyl) -3-cyclopentenyl group;

the compound represented by formula (I), where m is 0, and A is a 3-cyano-3-cyclohexenyl group;

the compound represented by formula (I), where m is 0, and A is a 3-fluoro-3-cyclohexenyl group;

the compound represented by formula (I), where m is 0, and A is a 3-ethynyl-3-cyclohexenyl group;

the compound represented by formula (I), where m is 0, and A is a 3- (1-propynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 0, and A is a 3- (2-propynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 0, and A is a 3- (2-butynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 0, and A is a 4-cyano-3-cyclohexenyl group;

the compound represented by formula (I), where m is 0, and A is a 4-fluoro-3-cyclohexenyl group;

the compound represented by formula (I), where m is 0, and A is a 4-ethynyl-3-cyclohexenyl group;

the compound represented by formula (I), where m is 0, and A is 4- (1-propynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 0, and A is 4- (2-propynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 0, and A is 4- (1-butynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 0, and A is 4- (2-butynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 0, and A is 4- (3-methoxy-1-propinyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 0, and A is 4- (3-methoxy-1-butynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 0, and A is 4- (4-methoxy-1-butynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 0, and A is 4- (4-methoxy-2-butynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 0, and A is 4- (3-methoxy-1-pentenyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 0, and A is 4- (4-methoxy-1-pentenyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 0, and A is 4- (5-methoxy-1-pentenyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 0, and A is 4- (4-methoxy-2-pentenyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 0, and A is 4- (5-methoxy-2-pentenyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 0, and A is 4- (3-dimethylamino-1-propyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 0, and A is 4- (3-dimethylamino-1-butynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 0, and A is 4- (4-dimethylamino-1-butynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 0, and A is 4- (4-dimethylamino-2-butynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 0, and A is 4- (3-dimethylamino-1-pentenyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 0, and A is 4- (4-dimethylamino-1-pentenyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 0, and A is 4- (5-dimethylamino-1-pentenyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 0, and A is 4- (4-dimethylamino-2-pentenyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 0, and A is 4- (5-dimethylamino-2-pentenyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 0, and A is 4- (3-methoxycarbonyl-1-propynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 0, and A is 4- (3-methoxycarbonyl-1-butynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 0, and A is 4- (4-methoxycarbonyl-1-butynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 0, and A is 4- (4-methoxycarbonyl-2-butynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 0, and A is 4- (3-methoxycarbonyl-1-pentenyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 0, and A is 4- (4-methoxycarbonyl-1-pentenyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 0, and A is 4- (5-methoxycarbonyl-1-pentenyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 0, and A is 4- (4-methoxycarbonyl-2-pentenyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 0, and A is 4- (5-methoxycarbonyl-2-pentenyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 0, and A is 4- (2-bromoethynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 0, and A is 4- (2-iodoethynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 0, and A is 4- (3-fluoro-1-propynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 0, and A is 4- (3,3-difluoro-1-propynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 0, and A is 4- (3,3,3-trifluoro-1-propynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 0, and A is 4- (1-fluoro-2-propynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 0, and A is 4- (1,1-difluoro-2-propynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 0, and A is 4- (3-fluoro-1-butynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 0, and A is 4- (4-fluoro-1-butynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 0, and A is 4- (3-fluoro-1-pentenyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 0, and A is 4- (4-fluoro-1-pentenyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 0, and A is 4- (5-fluoro-1-pentenyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, and A is a 3-cyanocyclopentyl group;

the compound represented by formula (I), where m is 1, and A is a 3-fluorocyclopentyl group;

the compound represented by formula (I), where m is 1, and A is a 3,3-difluorocyclopentyl group;

the compound represented by formula (I), where m is 1, and A is a 3-ethynylcyclopentyl group;

the compound represented by formula (I), where m is 1, and A is a 3- (1-propynyl) cyclopentyl group;

the compound represented by formula (I), where m is 1 and A is a 3- (2-propynyl) cyclopentyl group;

the compound represented by formula (I), where m is 1, and A is a 3- (2-butynyl) cyclopentyl group;

the compound represented by formula (I), where m is 1, and A is a 3-cyanocyclohexyl group;

the compound represented by formula (I), where m is 1, and A is a 3-fluorocyclohexyl group;

the compound represented by formula (I), where m is 1, and A is a 3,3-difluorocyclohexyl group;

the compound represented by formula (I), where m is 1, and A is a 3-ethynylcyclohexyl group;

the compound represented by formula (I), where m is 1 and A is a 3- (1-propynyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, and A is a 3- (2-propynyl) cyclohexyl group;

the compound represented by formula (I), where m is 1 and A is a 3- (2-butynyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, and A is a 4-cyanocyclohexyl group;

the compound represented by formula (I), where m is 1, and A is a 3-fluoro-4-cyanocyclohexyl group;

the compound represented by formula (I), where m is 1, and A is a 4-fluoro-4-cyanocyclohexyl group;

the compound represented by formula (I), where m is 1, and A is a 4-fluorocyclohexyl group;

the compound represented by formula (I), where m is 1, and A is a 4,4-difluorocyclohexyl group;

the compound represented by formula (I), where m is 1, and A is a 4-ethynylcyclohexyl group;

the compound represented by formula (I), where m is 1, and A is a 3-fluoro-4-ethynylcyclohexyl group;

the compound represented by formula (I), where m is 1, and A is a 4-fluoro-4-ethynylcyclohexyl group;

the compound represented by formula (I), where m is 1, and A is 4- (1-propynyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, and A is 4- (2-propynyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, and A is 4- (1-butynyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, and A is 4- (2-butynyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, and A is 4- (3-methoxy-1-propinyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, and A is 4- (3-methoxy-1-butynyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, and A is 4- (4-methoxy-1-butynyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, and A is 4- (4-methoxy-2-butynyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, and A is 4- (3-methoxy-1-pentenyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, and A is 4- (4-methoxy-1-pentenyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, and A is 4- (5-methoxy-1-pentenyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, and A is 4- (4-methoxy-2-pentenyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, and A is 4- (5-methoxy-2-pentenyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, and A is 4- (3-dimethylamino-1-propynyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, and A is 4- (3-dimethylamino-1-butynyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, and A is 4- (4-dimethylamino-1-butynyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, and A is 4- (4-dimethylamino-2-butynyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, and A is 4- (3-dimethylamino-1-pentenyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, and A is 4- (4-dimethylamino-1-pentenyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, and A is 4- (5-dimethylamino-1-pentenyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, and A is 4- (4-dimethylamino-2-pentenyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, and A is 4- (5-dimethylamino-2-pentenyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, and A is 4- (2-methoxycarbonylethynyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, and A is 4- (3-methoxycarbonyl-1-propynyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, and A is 4- (3-methoxycarbonyl-1-butynyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, and A is 4- (4-methoxycarbonyl-1-butynyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, and A is 4- (4-methoxycarbonyl-2-butynyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, and A is 4- (3-methoxycarbonyl-1-pentenyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, and A is 4- (4-methoxycarbonyl-1-pentenyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, and A is 4- (5-methoxycarbonyl-1-pentenyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, and A is 4- (4-methoxycarbonyl-2-pentenyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, and A is 4- (5-methoxycarbonyl-2-pentenyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, and A is 4- (2-bromoethynyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, and A is 4- (2-iodoethynyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, and A is 4- (3-fluoro-1-propinyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, and A is 4- (3,3-difluoro-1-propynyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, and A is 4- (3,3,3-trifluoro-1-propynyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, and A is 4- (1-fluoro-2-propinyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, and A is 4- (1,1-difluoro-2-propinyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, and A is 4- (3-fluoro-1-butynyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, and A is 4- (4-fluoro-1-butynyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, and A is 4- (3-fluoro-1-pentenyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, and A is 4- (4-fluoro-1-pentenyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, and A is 4- (5-fluoro-1-pentenyl) cyclohexyl group;

the compound represented by formula (I), where m is 2, and A is a 3-cyanocyclopentyl group;

the compound represented by formula (I), where m is 2, and A is a 3-fluorocyclopentyl group;

the compound represented by formula (I), where m is 2, and A is a 3,3-difluorocyclopentyl group;

the compound represented by formula (I), where m is 2, and A is a 3-ethynylcyclopentyl group;

the compound represented by formula (I), where m is 2, and A is a 3- (1-propynyl) cyclopentyl group;

the compound represented by formula (I), where m is 2, and A is a 3- (1-butynyl) cyclopentyl group;

the compound represented by formula (I), where m is 2, and A is a 3-cyanocyclohexyl group;

the compound represented by formula (I), where m is 2, and A is a 3-fluorocyclohexyl group;

the compound represented by formula (I), where m is 2, and A is a 3,3-difluorocyclohexyl group;

the compound represented by formula (I), where m is 2, and A is a 3-ethynylcyclohexyl group;

the compound represented by formula (I), where m is 2 and A is a 3- (1-propynyl) cyclohexyl group;

the compound represented by formula (I), where m is 2 and A is a 3- (1-butynyl) cyclohexyl group;

the compound represented by formula (I), where m is 2, and A is a 4-cyanocyclohexyl group;

the compound represented by formula (I), where m is 2, and A is a 4-fluorocyclohexyl group;

the compound represented by formula (I), where m is 2, and A is a 4,4-difluorocyclohexyl group;

the compound represented by formula (I), where m is 2, and A is a 4-ethynylcyclohexyl group;

the compound represented by formula (I), where m is 2, and A is a 4-fluoro-4-ethynylcyclohexyl group;

the compound represented by formula (I), where m is 2, and A is 4- (1-propynyl) cyclohexyl group;

the compound represented by formula (I), where m is 2, and A is 4- (1-butynyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, and A is a 3-cyano-3-cyclopentenyl group;

the compound represented by formula (I), where m is 1, and A is a 3-fluoro-3-cyclopentenyl group;

the compound represented by formula (I), where m is 1, and A is a 3-ethynyl-3-cyclopentenyl group;

the compound represented by formula (I), where m is 1, and A is a 3- (1-propynyl) -3-cyclopentenyl group;

the compound represented by formula (I), where m is 1, and A is a 3- (2-propynyl) -3-cyclopentenyl group;

the compound represented by formula (I), where m is 1, and A is a 3- (2-butynyl) -3-cyclopentenyl group;

the compound represented by formula (I), where m is 1, and A is a 3-cyano-3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, and A is a 3-fluoro-3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, and A is a 3-ethynyl-3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, and A is a 3- (1-propynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, and A is a 3- (2-propynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, and A is a 3- (2-butynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, and A is a 4-cyano-3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, and A is a 4-fluoro-3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, and A is a 4-ethynyl-3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, and A is 4- (1-propynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, and A is 4- (2-propynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, and A is 4- (1-butynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1 and A is a 4- (2-butynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, and A is 4- (3-methoxy-1-propinyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, and A is 4- (3-methoxy-1-butynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, and A is 4- (4-methoxy-1-butynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, and A is 4- (4-methoxy-2-butynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, and A is 4- (3-methoxy-1-pentenyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, and A is 4- (4-methoxy-1-pentenyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, and A is 4- (5-methoxy-1-pentenyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, and A is 4- (4-methoxy-2-pentenyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, and A is 4- (5-methoxy-2-pentenyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, and A is 4- (3-dimethylamino-1-propynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, and A is 4- (3-dimethylamino-1-butynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, and A is 4- (4-dimethylamino-1-butynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, and A is 4- (4-dimethylamino-2-butynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, and A is 4- (3-dimethylamino-1-pentenyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, and A is 4- (4-dimethylamino-1-pentenyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, and A is 4- (5-dimethylamino-1-pentenyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, and A is 4- (4-dimethylamino-2-pentenyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, and A is 4- (5-dimethylamino-2-pentenyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, and A is 4- (3-methoxycarbonyl-1-propynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, and A is 4- (3-methoxycarbonyl-1-butynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, and A is 4- (4-methoxycarbonyl-1-butynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, and A is 4- (4-methoxycarbonyl-2-butynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, and A is 4- (3-methoxycarbonyl-1-pentenyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, and A is 4- (4-methoxycarbonyl-1-pentenyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, and A is 4- (5-methoxycarbonyl-1-pentenyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, and A is 4- (4-methoxycarbonyl-2-pentenyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, and A is 4- (5-methoxycarbonyl-2-pentenyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1 and A is a 4- (2-bromoethynyl-3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, and A is 4- (2-iodoethynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, and A is 4- (3-fluoro-1-propynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, and A is 4- (3,3-difluoro-1-propynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, and A is 4- (3,3,3-trifluoro-1-propynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, and A is 4- (1-fluoro-2-propynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1 and A is 4- (1,1-difluoro-2-propynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, and A is 4- (3-fluoro-1-butynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, and A is 4- (4-fluoro-1-butynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, and A is 4- (3-fluoro-1-pentenyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, and A is 4- (4-fluoro-1-pentenyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, and A is 4- (5-fluoro-1-pentenyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 2, and A is a 3-cyclopentenyl group;

the compound represented by formula (I), where m is 2, and A is a 3-cyano-3-cyclopentenyl group;

the compound represented by formula (I), where m is 2, and A is a 3-fluoro-3-cyclopentenyl group;

the compound represented by formula (I), where m is 2, and A is a 3-ethynyl-3-cyclopentenyl group;

the compound represented by formula (I), where m is 2 and A is a 3- (1-propynyl) -3-cyclopentenyl group;

the compound represented by formula (I), where m is 2, and A is a 3- (1-butynyl) -3-cyclopentenyl group;

the compound represented by formula (I), where m is 2, and A is a 3-cyclohexenyl group;

the compound represented by formula (I), where m is 2, and A is a 3-cyano-3-cyclohexenyl group;

the compound represented by formula (I), where m is 2, and A is a 3-fluoro-3-cyclohexenyl group;

the compound represented by formula (I), where m is 2, and A is a 3-ethenyl-3-cyclohexenyl group;

the compound represented by formula (I), where m is 2 and A is a 3- (1-propynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 2 and A is a 3- (1-butynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, and A is a 3-methoxyiminocyclopentyl group;

the compound represented by formula (I), where m is 1, and A is a 3-ethoxyiminocyclopentyl group;

the compound represented by formula (I), where m is 1, and A is a 3-methoxyiminocyclohexyl group;

the compound represented by formula (I), where m is 1, and A is a 3-ethoxyiminocyclohexyl group;

the compound represented by formula (I), where m is 1, and A is a 4-methoxyiminocyclohexyl group;

the compound represented by formula (I), where m is 1, and A is a 4-ethoxyiminocyclohexyl group;

the compound represented by formula (I), where m is 2, and A is a 3-methoxyiminocyclopentyl group;

the compound represented by formula (I), where m is 2, and A is a 3-ethoxyiminocyclopentyl group;

the compound represented by formula (I), where m is 2, and A is a 3-methoxyiminocyclohexyl group;

the compound represented by formula (I), where m is 2, and A is a 3-ethoxyiminocyclohexyl group;

the compound represented by formula (I), where m is 2, and A is a 4-methoxyiminocyclohexyl group;

the compound represented by formula (I), where m is 2, and A is a 4-ethoxyiminocyclohexyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is a 3-cyanocyclopentyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is a 3-fluorocyclopentyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is a 3,3-difluorocyclopentyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is a 3-ethynylcyclopentyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is a 3- (1-propyl) cyclopentyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is a 3- (2-propyl) cyclopentyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is a 3- (2-butynyl) cyclopentyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is a 3-cyanocyclohexyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is a 3-fluorocyclohexyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is a 3,3-difluorocyclohexyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is a 3-ethynylcyclohexyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is a 3- (1-propynyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is a 3- (2-propynyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is a 3- (2-butynyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is a 4-cyanocyclohexyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is a 3-fluoro-4-cyanocyclohexyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is a 4-fluoro-4-cyanocyclohexyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is a 4-fluorocyclohexyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is a 4,4-difluorocyclohexyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is a 4-ethynylcyclohexyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is a 3-fluoro-4-ethynylcyclohexyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is a 4-fluoro-4-ethynylcyclohexyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is a 4- (1-propynyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is a 4- (2-propynyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is a 4- (1-butynyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is a 4- (2-butynyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is a 4- (3-methoxy-1-propinyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (3-methoxy-1-butynyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (4-methoxy-1-butynyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is a 4- (4-methoxy-2-butynyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (3-methoxy-1-pentenyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (4-methoxy-1-pentenyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (5-methoxy-1-pentenyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (4-methoxy-2-pentenyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (5-methoxy-2-pentenyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (3-dimethylamino-1-propynyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (3-dimethylamino-1-butynyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (4-dimethylamino-1-butynyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (4-dimethylamino-2-butynyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (3-dimethylamino-1-pentenyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (4-dimethylamino-1-pentenyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (5-dimethylamino-1-pentenyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (4-dimethylamino-2-pentenyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (5-dimethylamino-2-pentenyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (2-methoxycarbonyl-ethynyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (3-methoxycarbonyl-1-propinyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (3-methoxycarbonyl-1-butynyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (4-methoxycarbonyl-1-butynyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (4-methoxycarbonyl-2-butynyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (3-methoxycarbonyl-1-pentenyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (4-methoxycarbonyl-1-pentenyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (5-methoxycarbonyl-1-pentenyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (4-methoxycarbonyl-2-pentenyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (5-methoxycarbonyl-2-pentenyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is a 4- (2-bromoethynyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (2-iodoethynyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (3-fluoro-1-propynyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is a 4- (3,3-difluoro-1-propinyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (3,3,3-trifluoro-1-propynyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is a 4- (1-fluoro-2-propynyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is a 4- (1,1-difluoro-2-propinyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (3-fluoro-1-butynyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, A is a 4- (4-fluoro-1-butynyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (3-fluoro-1-pentenyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (4-fluoro-1-pentenyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (5-fluoro-1-pentenyl) cyclohexyl group;

the compound represented by formula (I), where m is 2, R ³ and R ⁴ are hydrogen atoms, and A is a 3-cyanocyclopentyl group;

the compound represented by formula (I), where m is 2, R ³ and R ⁴ are hydrogen atoms, and A is a 3-fluorocyclopentyl group;

the compound represented by formula (I), where m is 2, R ³ and R ⁴ are hydrogen atoms, and A is a 3,3-difluorocyclopentyl group;

the compound represented by formula (I), where m is 2, R ³ and R ⁴ are hydrogen atoms, and A is a 3-ethynylcyclopentyl group;

the compound represented by formula (I), where m is 2, R ³ and R ⁴ are hydrogen atoms, and A is a 3- (1-propyl) cyclopentyl group;

the compound represented by formula (I), where m is 2, R ³ and R ⁴ are hydrogen atoms, and A is a 3- (1-butynyl) cyclopentyl group;

the compound represented by formula (I), where m is 2, R ³ and R ⁴ are hydrogen atoms, and A is a 3-cyanocyclohexyl group;

the compound represented by formula (I), where m is 2, R ³ and R ⁴ are hydrogen atoms, and A is a 3-fluorocyclohexyl group;

the compound represented by formula (I), where m is 2, R ³ and R ⁴ are hydrogen atoms, and A is a 3,3-difluorocyclohexyl group;

the compound represented by formula (I), where m is 2, R ³ and R ⁴ are hydrogen atoms, and A is a 3-ethynylcyclohexyl group;

the compound represented by formula (I), where m is 2, R ³ and R ⁴ are hydrogen atoms, and A is a 3- (1-propynyl) cyclohexyl group;

the compound represented by formula (I), where m is 2, R ³ and R ⁴ are hydrogen atoms, and A is a 3- (1-butynyl) cyclohexyl group;

the compound represented by formula (I), where m is 2, R ³ and R ⁴ are hydrogen atoms, and A is a 4-cyanocyclohexyl group;

the compound represented by formula (I), where m is 2, R ³ and R ⁴ are hydrogen atoms, and A is a 4-fluorocyclohexyl group;

the compound represented by formula (I), where m is 2, R ³ and R ⁴ are hydrogen atoms, and A is a 4,4-difluorocyclohexyl group;

the compound represented by formula (I), where m is 2, R ³ and R ⁴ are hydrogen atoms, and A is a 4-ethynylcyclohexyl group;

the compound represented by formula (I), where m is 2, R ³ and R ⁴ are hydrogen atoms, and A is a 4-fluoro-4-ethynylcyclohexyl group;

the compound represented by formula (I), where m is 2, R ³ and R ⁴ are hydrogen atoms, and A is a 4- (1-propynyl) cyclohexyl group;

the compound represented by formula (I), where m is 2, R ³ and R ⁴ are hydrogen atoms, and A is a 4- (1-butynyl) cyclohexyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is a 3-cyano-3-cyclopentenyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is a 3-fluoro-3-cyclopentenyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is a 3-ethynyl-3-cyclopentenyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is a 3- (1-propynyl) -3-cyclopentenyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is a 3- (2-propynyl) -3-cyclopentenyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is a 3- (2-butynyl) -3-cyclopentenyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is a 3-cyano-3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is a 3-fluoro-3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is a 3-ethynyl-3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is a 3- (1-propynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is a 3- (2-propynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is a 3- (2-butynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is a 4-cyano-3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is a 4-fluoro-3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is a 4-ethynyl-3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is a 4- (1-propynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is a 4- (2-propynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is a 4- (1-butynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is a 4- (2-butynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (3-methoxy-1-propynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (3-methoxy-1-butynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (4-methoxy-1-butynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (4-methoxy-2-butynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (3-methoxy-1-pentenyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (4-methoxy-1-pentenyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (5-methoxy-1-pentenyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (4-methoxy-2-pentenyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (5-methoxy-2-pentenyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (3-dimethylamino-1-propynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (3-dimethylamino-1-butynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (4-dimethylamino-1-butynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (4-dimethylamino-2-butynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (3-dimethylamino-1-pentenyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (4-dimethylamino-1-pentenyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (5-dimethylamino-1-pentenyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (4-dimethylamino-2-pentenyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (5-dimethylamino-2-pentenyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (3-methoxycarbonyl-1-propinyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (3-methoxycarbonyl-1-butynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (4-methoxycarbonyl-1-butynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (4-methoxycarbonyl-2-butynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (3-methoxycarbonyl-1-pentenyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (4-methoxycarbonyl-1-pentenyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (5-methoxycarbonyl-1-pentenyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (4-methoxycarbonyl-2-pentenyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (5-methoxycarbonyl-2-pentenyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is a 4- (2-bromoethynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is a 4- (2-iodoethynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (3-fluoro-1-propynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (3,3-difluoro-1-propynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (3,3,3-trifluoro-1-propynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (1-fluoro-2-propynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (1,1-difluoro-2-propynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (3-fluoro-1-butynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (4-fluoro-1-butynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (3-fluoro-1-pentenyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (4-fluoro-1-pentenyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is 4- (5-fluoro-1-pentenyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 2, R ³ and R ⁴ are hydrogen atoms, and A is a 3-cyclopentenyl group;

the compound represented by formula (I), where m is 2, R ³ and R ⁴ are hydrogen atoms, and A is a 3-cyano-3-cyclopentenyl group;

the compound represented by formula (I), where m is 2, R ³ and R ⁴ are hydrogen atoms, and A is a 3-fluoro-3-cyclopentenyl group;

the compound represented by formula (I), where m is 2, R ³ and R ⁴ are hydrogen atoms, and A is a 3-ethynyl-3-cyclopentenyl group;

the compound represented by formula (I), where m is 2, R ³ and R ⁴ are hydrogen atoms, and A is a 3- (1-propynyl) -3-cyclopentenyl group;

the compound represented by formula (I), where m is 2, R ³ and R ⁴ are hydrogen atoms, and A is a 3- (1-butynyl) -3-cyclopentenyl group;

the compound represented by formula (I), where m is 2, R ³ and R ⁴ are hydrogen atoms, and A is a 3-cyclohexenyl group;

the compound represented by formula (I), where m is 2, R ³ and R ⁴ are hydrogen atoms, and A is a 3-cyano-3-cyclohexenyl group;

the compound represented by formula (I), where m is 2, R ³ and R ⁴ are hydrogen atoms, and A is a 3-fluoro-3-cyclohexenyl group;

the compound represented by formula (I), where m is 2, R ³ and R ⁴ are hydrogen atoms, and A is a 3-ethynyl-3-cyclohexenyl group;

the compound represented by formula (I), where m is 2, R ³ and R ⁴ are hydrogen atoms, and A is a 3- (1-propynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 2, R ³ and R ⁴ are hydrogen atoms, and A is a 3- (1-butynyl) -3-cyclohexenyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is a 3-methoxyiminocyclopentyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is a 3-ethoxyiminocyclopentyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is a 3-methoxyiminocyclohexyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is a 3-ethoxyiminocyclohexyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is a 4-methoxyiminocyclohexyl group;

the compound represented by formula (I), where m is 1, R ³ and R ⁴ are hydrogen atoms, and A is a 4-ethoxyiminocyclohexyl group;

the compound represented by formula (I), where m is 2, R ³ and R ⁴ are hydrogen atoms, and A is a 3-methoxyiminocyclopentyl group;

the compound represented by formula (I), where m is 2, R ³ and R ⁴ are hydrogen atoms, and A is a 3-ethoxyiminocyclopentyl group;

the compound represented by formula (I), where m is 2, R ³ and R ⁴ are hydrogen atoms, and A is a 3-methoxyiminocyclohexyl group;

the compound represented by formula (I), where m is 2, R ³ and R ⁴ are hydrogen atoms, and A is a 3-ethoxyiminocyclohexyl group;

the compound represented by formula (I), where m is 2, R ³ and R ⁴ are hydrogen atoms, and A is a 4-methoxyiminocyclohexyl group; and

the compound represented by formula (I), where m is 2, R ³ and R ⁴ are hydrogen atoms, and A is a 4-ethoxyiminocyclohexyl group.

The following explains the method of obtaining the compounds of the present invention.

The compound represented by formula (I-a), which is the compound of the present invention represented by formula (I), where n is 0, can be obtained, for example, using the following synthesis methods 1-4.

Synthesis Method 1

The compound represented by formula (I-a) can be obtained, for example, by reacting the following compound (a) and the following compound (b):

where A, Q, R ¹ , R ² , R ³ , R ⁴ and m are as defined above, and Z ¹ represents a leaving group, such as a chlorine atom, a bromine atom, an iodine atom or a methanesulfonyl group.

The reaction is carried out in a conventional solvent in the presence of a conventional base.

Examples of the solvent used in the reaction include ethers such as diethyl ether, tetrahydrofuran and dimethoxymethane, acid amides such as N, N-dimethylformamide, organosulfur compounds such as dimethyl sulfoxide and sulfolane, aliphatic hydrocarbons such as hexane and heptane, aromatic hydrocarbons, such as toluene and xylene, halogenated hydrocarbons, such as 1,2-dichloroethane and chlorobenzene, water and a mixture thereof.

Examples of the base used in the reaction include inorganic bases such as sodium hydride, sodium hydroxide, potassium hydroxide and potassium carbonate, alkali metal alkoxides such as sodium methylate and potassium tert-butylate, and organic bases such as triethylamine, 1,4-diazabicyclo [2.2.2] octane and 1,8-diazabicyclo [5.4.0] -7-undecene.

The amount used in the reaction of the base is usually from 1 to 10 moles per 1 mol of compound (a).

The amount of compound (b) used in the reaction is usually from 1 to 10 moles per 1 mol of compound (a).

The reaction temperature is usually maintained in the range from -50 to 100 ° C, and the reaction time is usually from 1 to 24 hours.

After completion of the reaction, compound (I-a) can be isolated, for example, by pouring the reaction mixture into water and extracting the resulting mixture with an organic solvent, followed by concentration. The isolated compound (I-a) can be further purified by chromatography, recrystallization or other similar methods, if necessary.

Synthesis Method 2

The compound represented by formula (I-a) can also be obtained, for example, by reacting the following compound (c) and compound (d):

where A, Q, R ¹ , R ² , R ³ , R ⁴ and m are as defined above, and Z ² represents a leaving group, such as a chlorine atom, a bromine atom, an iodine atom or a methanesulfonyl group.

The reaction is carried out in a conventional solvent in the presence of a conventional base.

Examples of the solvent used in the reaction include ethers such as diethyl ether, tetrahydrofuran and dimethoxymethane, acid amides such as N, N-dimethylformamide, organosulfur compounds such as dimethyl sulfoxide and sulfolane, aliphatic hydrocarbons such as hexane and heptane, aromatic hydrocarbons, such as toluene and xylene, halogenated hydrocarbons, such as 1,2-dichloroethane and chlorobenzene, water and a mixture thereof.

Examples of the base used in the reaction include inorganic bases such as sodium hydride, sodium hydroxide, potassium hydroxide and potassium carbonate, alkali metal alkoxides such as sodium methylate and potassium tert-butylate, and organic bases such as triethylamine, 1,4-diazabicyclo [2.2.2] octane and 1,8-diazabicyclo [5.4.0] -7-undecene.

The amount used in the reaction of the base is usually from 1 to 10 moles per 1 mol of compound (d).

The amount of compound (c) used in the reaction is usually from 1 to 10 moles per 1 mol of compound (d).

The reaction temperature is usually maintained in the range from -50 to 100 ° C, and the reaction time is usually from 1 to 24 hours.

After completion of the reaction, compound (I-a) can be isolated, for example, by pouring the reaction mixture into water and extracting the resulting mixture with an organic solvent, followed by concentration. The isolated compound (I-a) can be further purified by chromatography, recrystallization or other similar methods, if necessary.

Synthesis Method 3

The compound represented by formula (I-a) can also be obtained from compound (c) according to the following procedure:

where A, Q, R ¹ , R ² , R ³ , R ⁴ , m, Z ¹ and Z ² are as defined above, and R ²⁰ represents a methyl group or an amino group.

Stage (3-1):

Compound (f) can be obtained by reacting compound (c) with compound (e).

The reaction is carried out in a traditional solvent.

Examples of the solvent used in the reaction include halogenated hydrocarbons such as dichloromethane and chloroform, alcohols such as methanol and ethanol, and a mixture thereof.

The amount of compound (e) used in the reaction is usually from 1 to 3 moles per 1 mol of compound (c).

The reaction temperature is usually maintained in the range from 20 to 200 ° C, and the reaction time is usually from 0.5 to 240 hours.

After completion of the reaction, compound (f) can be isolated, for example, by concentration of the reaction mixture. The isolated compound (f) can be used as it is in stage (3-2) or, if necessary, can be further purified by recrystallization or other similar methods.

Stage (3-2):

The compound represented by formula (I-a) can be obtained by reacting compound (f) and compound (b) in the presence of a base.

The reaction is carried out in a conventional solvent in the presence of a conventional base.

Examples of the solvent used in the reaction include ethers such as diethyl ether, tetrahydrofuran and dimethoxymethane, acid amides such as N, N-dimethylformamide, organosulfur compounds such as dimethyl sulfoxide and sulfolane, aliphatic hydrocarbons such as hexane and heptane, aromatic hydrocarbons, such as toluene and xylene, halogenated hydrocarbons, such as 1,2-dichloroethane and chlorobenzene, water and a mixture thereof.

Examples of the base used in the reaction include inorganic bases such as sodium hydride, sodium hydroxide, potassium hydroxide and potassium carbonate, and alkali metal alkoxides such as sodium methylate and potassium tert-butylate.

The amount of the base used in the reaction is usually from 1 to 50 moles per 1 mol of compound (f).

The amount of compound (b) used in the reaction is usually from 1 to 10 moles per 1 mol of compound (f).

The reaction can be carried out using an interfacial transfer catalyst such as tetra-n-butylammonium bromide, if necessary.

The amount of phase transfer catalyst used is usually from 0.05 to 1.0 mol per 1 mol of compound (f).

The reaction temperature is usually maintained in the range from -50 to 100 ° C, and the reaction time is usually from 1 to 24 hours.

After completion of the reaction, compound (I-a) can be isolated, for example, by pouring the reaction mixture into water and extracting the resulting mixture with an organic solvent, followed by concentration. The isolated compound (I-a) can be further purified by chromatography, recrystallization or other similar methods, if necessary.

Synthesis Method 4

The compound represented by formula (I-a) can also be obtained from compound (c) according to the following procedure:

where A, Q, R ¹ , R ² , R ³ , R ⁴ , m, Z ¹ and Z ² are as defined above, and R ²¹ represents a methyl group or a phenyl group.

Stage (4-1):

Compound (h) can be obtained by reacting compound (b) with compound (g) in the presence of a base.

The reaction is carried out in a conventional solvent in the presence of a conventional base.

Examples of the solvent used in the reaction include ethers such as diethyl ether, tetrahydrofuran and dimethoxyethane, acid amides such as N, N-dimethylformamide, organosulfur compounds such as dimethyl sulfoxide and sulfolane, aliphatic hydrocarbons such as hexane and heptane, aromatic hydrocarbons, such as toluene and xylene, halogenated hydrocarbons such as 1,2-dichloroethane and chlorobenzene, and a mixture thereof.

Examples of the base used in the reaction include inorganic bases such as sodium hydride and potassium carbonate, and organic bases such as triethylamine, 1,4-diazabicyclo [2.2.2] octane and 1,8-diazabicyclo [5.4.0] -7- undecene.

The amount used in the reaction of the base is usually from 1 to 10 moles per 1 mol of compound (c).

The amount of compound (g) used in the reaction is usually from 1 to 5 moles per 1 mol of compound (b).

The reaction temperature is usually maintained in the range from -20 to 80 ° C, and the reaction time is usually from 1 to 24 hours.

After completion of the reaction, compound (h) can be isolated, for example, by pouring the reaction mixture into acidified water (for example, dilute hydrochloric acid, etc.) and extracting the resulting mixture with an organic solvent, followed by concentration. The isolated compound (h) can be further purified by chromatography, recrystallization, or other similar methods, if necessary.

Stage (4-2):

The compound represented by formula (I-a) can be obtained by reacting compound (c) and compound (h) in the presence of a base.

The reaction is carried out in a conventional solvent in the presence of a conventional base.

Examples of the solvent used in the reaction include ethers such as diethyl ether, tetrahydrofuran and dimethoxyethane, acid amides such as N, N-dimethylformamide, organosulfur compounds such as dimethyl sulfoxide and sulfolane, aliphatic hydrocarbons such as hexane and heptane, aromatic hydrocarbons, such as toluene and xylene, halogenated hydrocarbons, such as 1,2-dichloroethane and chlorobenzene, water and a mixture thereof.

Examples of the base used in the reaction include inorganic bases such as sodium hydroxide and potassium hydroxide, and alkali metal alcoholates such as sodium methylate, sodium ethylate and potassium tert-butylate.

The amount used in the reaction of the base is usually from 1 to 10 moles per 1 mol of compound (h).

The amount of compound (c) used in the reaction is usually from 1 to 10 moles per 1 mol of compound (h).

The reaction temperature is usually maintained in the range from -50 to 100 ° C, and the reaction time is usually from 1 to 24 hours.

After completion of the reaction, compound (I-a) can be isolated, for example, by pouring the reaction mixture into water and extracting the resulting mixture with an organic solvent, followed by concentration. The isolated compound (I-a) can be further purified by chromatography, recrystallization or other similar methods, if necessary.

Synthesis Method 5

The compound represented by formula (I-a) can also be obtained from compound (b) according to the following procedure:

where A, Q, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ²¹ , m, Z ¹ and Z ² are as defined above.

Stage (5-1):

Compound (i) can be prepared by reacting compound (b) with compound (g) in the presence of a base.

The reaction is carried out in a conventional solvent in the presence of a conventional base.

Examples of the solvent used in the reaction include ethers such as diethyl ether, tetrahydrofuran and dimethoxyethane, acid amides such as N, N-dimethylformamide, organosulfur compounds such as dimethyl sulfoxide and sulfolane, aliphatic hydrocarbons such as hexane and heptane, aromatic hydrocarbons, such as toluene and xylene, halogenated hydrocarbons such as 1,2-dichloroethane and chlorobenzene, and a mixture thereof.

Examples of the base used in the reaction include inorganic bases such as sodium hydride and potassium carbonate, and organic bases such as triethylamine, 1,4-diazabicyclo [2.2.2] octane and 1,8-diazabicyclo [5.4.0] -7- undecene.

The amount used in the reaction of the base is usually from 1 to 10 moles per 1 mol of compound (b).

The amount of compound (g) used in the reaction is usually from 1 to 5 moles per 1 mol of compound (b).

The reaction temperature is usually maintained in the range from -20 to 80 ° C, and the reaction time is usually from 1 to 24 hours.

After completion of the reaction, compound (h) can be isolated, for example, by pouring the reaction mixture into acidified water (for example, dilute hydrochloric acid, etc.) and extracting the resulting mixture with an organic solvent, followed by concentration. The isolated compound (h) can be further purified by chromatography, recrystallization, or other similar methods, if necessary.

Stage (5-2):

The compound represented by formula (I-a) can be obtained by reacting compound (c) with compound (i) in the presence of a base.

The reaction is carried out in a conventional solvent in the presence of a conventional base.

Examples of the solvent used in the reaction include ethers such as diethyl ether, tetrahydrofuran and dimethoxyethane, acid amides such as N, N-dimethylformamide, organosulfur compounds such as dimethyl sulfoxide and sulfolane, aliphatic hydrocarbons such as hexane and heptane, aromatic hydrocarbons, such as toluene and xylene, halogenated hydrocarbons, such as 1,2-dichloroethane and chlorobenzene, water and a mixture thereof.

Examples of the base used in the reaction include inorganic bases such as sodium hydroxide and potassium hydroxide, and alkali metal alcoholates such as sodium methylate, sodium ethylate and potassium tert-butylate.

The amount used in the reaction of the base is usually from 1 to 10 moles per 1 mol of compound (i).

The amount of compound (c) used in the reaction is usually from 1 to 10 moles per 1 mol of compound (i).

The reaction temperature is usually maintained in the range from -50 to 100 ° C, and the reaction time is usually from 1 to 24 hours.

After completion of the reaction, compound (I-a) can be isolated, for example, by pouring the reaction mixture into water and extracting the resulting mixture with an organic solvent, followed by concentration. The isolated compound (I-a) can be further purified by chromatography, recrystallization or other similar methods, if necessary.

Synthesis Method 6

A compound represented by formula (Ib) or (Ic), which is a compound of the present invention, represented by formula (I), wherein R ¹ is a C1-C4 chain hydrocarbon group optionally substituted with a halogen atom or a hydrogen atom, and R ² is a group -C (= O) R ⁵ or a cyano group, can be obtained from compound (j) according to the following procedure:

where A, Q, R ³ , R ⁴ , n and m are as defined above, Z ³ and Z ⁴ represent a leaving group such as a chlorine atom, bromine atom, iodine atom or methanesulfonyl group, R ^1a represents a hydrocarbon a C1-C4 chain group optionally substituted with a halogen atom, and R ^2a represents a —C (═O) R ⁵ group or a cyano group.

Stage (6-1):

The compound represented by formula (I-b) can be obtained by reacting compound (k) with compound (j) in the presence of a base.

The reaction is carried out in a conventional solvent in the presence of a base.

Examples of the solvent used in the reaction include ethers such as diethyl ether, tetrahydrofuran and diethoxyethane, acid amides such as N, N-dimethylformamide, organosulfur compounds such as dimethyl sulfoxide and sulfolane, aliphatic hydrocarbons such as hexane and heptane, aromatic hydrocarbons, such as toluene and xylene, halogenated hydrocarbons such as 1,2-dichloroethane and chlorobenzene, and a mixture thereof.

Examples of the base used in the reaction include inorganic bases such as sodium hydride, sodium hydroxide, potassium hydroxide and potassium carbonate, alkali metal alkoxides such as sodium methylate and potassium tert-butylate, and organic bases such as triethylamine, 1,4-diazabicyclo [2.2.2] octane and 1,8-diazabicyclo [5.4.0] -7-undecene.

The amount of the base used in the reaction is usually from 1 to 10 moles per 1 mol of compound (j).

The amount of compound (k) used in the reaction is usually from 1 to 10 moles per 1 mol of compound (j).

The reaction temperature is usually maintained in the range from -50 to 100 ° C, and the reaction time is usually from 1 to 24 hours.

After completion of the reaction, compound (I-b) can be isolated, for example, by pouring the reaction mixture into acidified water (for example, dilute hydrochloric acid, etc.) and extracting the resulting mixture with an organic solvent, followed by concentration. The isolated compound (I-b) can be further purified by chromatography, recrystallization, or other similar methods, if necessary.

Stage (6-2):

The compound represented by formula (I-c) can be obtained by reacting compound (l) with compound (I-b) in the presence of a base.

The reaction is carried out in a conventional solvent in the presence of a conventional base.

Examples of the solvent used in the reaction include ethers such as diethyl ether, tetrahydrofuran and dimethoxyethane, acid amides such as N, N-dimethylformamide, organosulfur compounds such as dimethyl sulfoxide and sulfolane, aliphatic hydrocarbons such as hexane and heptane, aromatic hydrocarbons, such as toluene and xylene, halogenated hydrocarbons, such as 1,2-dichloroethane and chlorobenzene, water and a mixture thereof.

Examples of the base used in the reaction include inorganic bases such as sodium hydride, sodium hydroxide, potassium hydroxide and potassium carbonate, alkali metal alkoxides such as sodium methylate and potassium tert-butylate, and organic bases such as triethylamine, 1,4-diazabicyclo [2.2.2] octane and 1,8-diazabicyclo [5.4.0] -7-undecene.

The amount used in the reaction of the base is usually from 1 to 10 moles per 1 mol of compound (I-b).

The amount of the compound (l) used in the reaction is usually from 1 to 10 moles per 1 mol of the compound (I-b).

The reaction temperature is usually maintained in the range from -50 to 100 ° C, and the reaction time is usually from 1 to 24 hours.

After completion of the reaction, compound (I-c) can be isolated, for example, by pouring the reaction mixture into water and extracting the resulting mixture with an organic solvent, followed by concentration. The isolated compound (I-c) can be further purified by chromatography, recrystallization or other similar methods, if necessary.

Synthesis Method 7

Compound (Ic), which is a compound of the present invention represented by formula (I), wherein R ¹ is a C1-C4 chain hydrocarbon group optionally substituted with a halogen atom or a hydrogen atom, and R ² is a —C (= O) group R ⁵ or cyano can also be obtained from compound (j) according to the following procedure:

where A, Q, R ^1a , R ^2a , R ³ , R ⁴ , n, m, Z ³ and Z ⁴ are as defined above.

Stage (7-1):

Compound (q) can be obtained by reacting compound (k) with compound (j) in the presence of a base.

The reaction is carried out in a conventional solvent in the presence of a conventional base.

Examples of the solvent used in the reaction include ethers such as diethyl ether, tetrahydrofuran and dimethoxyethane, acid amides such as N, N-dimethylformamide, organosulfur compounds such as dimethyl sulfoxide and sulfolane, aliphatic hydrocarbons such as hexane and heptane, aromatic hydrocarbons, such as toluene and xylene, halogenated hydrocarbons, such as 1,2-dichloroethane and chlorobenzene, water and a mixture thereof.

Examples of the base used in the reaction include inorganic bases such as sodium hydride, sodium hydroxide, potassium hydroxide and potassium carbonate, alkali metal alkoxides such as sodium methylate and potassium tert-butylate, and organic bases such as triethylamine, 1,4-diazabicyclo [2.2.2] octane and 1,8-diazabicyclo [5.4.0] -7-undecene.

The amount of the base used in the reaction is usually from 1 to 10 moles per 1 mol of compound (j).

The amount of compound (k) used in the reaction is usually from 1 to 10 moles per 1 mol of compound (j).

The reaction temperature is usually maintained in the range from -50 to 100 ° C, and the reaction time is usually from 1 to 24 hours.

After completion of the reaction, compound (q) can be isolated, for example, by pouring the reaction mixture into water and extracting the resulting mixture with an organic solvent, followed by concentration. The isolated compound (q) can be further purified by chromatography, recrystallization, or other similar methods, if necessary.

Stage (7-2):

The compound represented by formula (I-c) can be obtained by reacting compound (l) with compound (q) in the presence of a base.

The reaction is carried out in a conventional solvent in the presence of a conventional base.

Examples of the solvent used in the reaction include ethers such as diethyl ether, tetrahydrofuran and dimethoxyethane, acid amides such as N, N-dimethylformamide, organosulfur compounds such as dimethyl sulfoxide and sulfolane, aliphatic hydrocarbons such as hexane and heptane, aromatic hydrocarbons, such as toluene and xylene, halogenated hydrocarbons, such as 1,2-dichloroethane and chlorobenzene, water and a mixture thereof.

Examples of the base used in the reaction include inorganic bases such as sodium hydride, sodium hydroxide, potassium hydroxide and potassium carbonate, alkali metal alkoxides such as sodium methylate and potassium tert-butylate, and organic bases such as triethylamine, 1,4-diazabicyclo [2.2.2] octane and 1,8-diazabicyclo [5.4.0] -7-undecene.

The amount used in the reaction of the base is usually from 1 to 10 moles per 1 mol of compound (I-b).

The amount of compound (l) used in the reaction is usually from 1 to 10 moles per 1 mol of compound (q).

The reaction temperature is usually maintained in the range from -50 to 100 ° C, and the reaction time is usually from 1 to 24 hours.

After completion of the reaction, compound (I-c) can be isolated, for example, by pouring the reaction mixture into water and extracting the resulting mixture with an organic solvent, followed by concentration. The isolated compound (I-c) can be further purified by chromatography, recrystallization or other similar methods, if necessary.

Synthesis Method 8

A compound represented by formula (Id), which is a compound of the present invention, represented by formula (I), wherein R ¹ is a halogen atom and R ² is a —C (= O) R ⁵ group or a cyano group, can be prepared from compound (Ib ) according to the following procedure:

where A, Q, R ^2a , R ³ , R ⁴ , n and m are as defined above, and R ^1b represents a halogen atom.

The reaction is carried out in a conventional solvent in the presence of a conventional base.

Examples of the solvent used in the reaction include acid amides such as N, N-dimethylformamide, ethers such as diethyl ether and tetrahydrofuran, organosulfur compounds such as dimethyl sulfoxide and sulfolane, halogenated hydrocarbons such as chloroform, carbon tetrachloride, 1,2-dichloroethane , dichloromethane and dichlorobenzene, aliphatic nitriles such as acetonitrile and propionitrile, aromatic hydrocarbons such as toluene and xylene, water and a mixture thereof.

Examples of the base used in the reaction include inorganic bases such as sodium hydride, sodium hydroxide, potassium hydroxide and potassium carbonate, alkali metal alkoxides such as sodium methylate and potassium tert-butylate, and organic bases such as triethylamine, 1,4-diazabicyclo [2.2.2] octane and 1,8-diazabicyclo [5.4.0] -7-undecene.

The amount used in the reaction of the base is usually from 1 to 10 moles per 1 mol of compound (I-b).

Examples of the halogenating reagent A used in the reaction include halogenated hydrocarbons such as carbon tetrachloride and hexachloroethane, halogens such as fluorine, chlorine, bromine and iodine, N-halogenated succinimide, such as N-chlorosuccinimide, N-bromosuccinimide and N-iodosuccinimide, salts N-fluoropyridinium, such as 1-fluoro-2,4,6-trimethylpyridinium trifluoromethanesulfonate and 1,1'-difluoro-2,2'-bipyridinium bistetrafluoroborate, and inorganic salts such as copper (II) chloride and copper (II bromide )

The amount of halogenating reagent used in the reaction is usually from 1 to 10 moles per 1 mol of compound (I-b).

The reaction temperature is usually maintained in the range from -100 to 100 ° C, and the reaction time is usually from 1 to 24 hours.

After completion of the reaction, compound (I-d) can be isolated, for example, by pouring the reaction mixture into water and extracting the resulting mixture with an organic solvent, followed by concentration. The isolated compound (I-d) can be further purified by chromatography, recrystallization, or other similar methods, if necessary.

Synthesis Method 9

A compound represented by formula (Id), which is a compound of the present invention, represented by formula (I), wherein R ¹ is a halogen atom and R ² is a —C (= O) R ⁵ group or a cyano group, can be prepared from compound (Ib ) according to the following procedure:

where A, Q, R ^1b , R ^2a , R ³ , R ⁴ , n and m are as defined above.

The reaction is carried out in a traditional solvent.

Examples of the solvent used in the reaction include halogenated hydrocarbons such as chloroform, carbon tetrachloride, 1,2-dichloroethane, dichloromethane and dichlorobenzene, aliphatic nitriles such as acetonitrile and propionitrile, aromatic hydrocarbons such as toluene and xylene, aliphatic carboxylic acids, such as acetic acid, carbon disulfide, water and their mixture.

Examples of the halogenating reagent B used in the reaction include halogens such as fluorine, chlorine, bromine and iodine, hydrogen halide such as hydrogen fluoride, hydrogen chloride, hydrogen bromide and hydrogen iodide, sulfur halide compounds such as thionyl chloride, thionyl bromide and sulfuryl chloride, and phosphorus halide compounds such as phosphorus trichloride, phosphorus tribromide, phosphorus pentachloride and phosphorus oxychloride.

The amount of halogenating reagent used in the reaction is usually from 1 to 10 moles per 1 mol of compound (I-b).

The reaction temperature is usually maintained in the range from -100 to 200 ° C, and the reaction time is usually from 1 to 24 hours.

After completion of the reaction, compound (I-d) can be isolated, for example, by pouring the reaction mixture into water and extracting the resulting mixture with an organic solvent, followed by concentration. The isolated compound (I-d) can be further purified by chromatography, recrystallization, or other similar methods, if necessary.

Synthesis Method 10

The compound represented by formula (I-e), which is the compound of the present invention represented by formula (I), where n is 1 or 2, can be obtained by oxidizing the compound represented by formula (I-a):

where A, Q, R ¹ , R ² , R ³ , R ⁴ and m are as defined above, and n ′ is 1 or 2.

The reaction is carried out in a traditional solvent.

Examples of the solvent used in the reaction include alcohols, such as methanol and ethanol, halogenated hydrocarbons, such as dichloromethane and chloroform, aromatic hydrocarbons, such as toluene and xylene, aliphatic carboxylic acids, such as acetic acid and trifluoroacetic acid, water, and a mixture thereof.

Examples of the oxidizing agent used in the reaction include organic peroxides such as peracetic acid, trifluorooracetic acid and m-chloroperbenzoic acid, halogen molecules such as chlorine and bromine, halogen-containing imides such as N-chlorosuccinimide, halogenated perchloric acid compounds (or its salts), iodic acid (or its salts) and other similar compounds, permanganates such as potassium permanganate, chromates such as potassium chromate, peroxysulfates such as potassium persulfate, and hydrogen peroxide.

The amount of oxidizing agent used in the reaction is usually from 1 to 10 moles per 1 mol of compound (I-a).

The reaction temperature is usually maintained in the range from -50 to 200 ° C, and the reaction time is usually from 1 to 72 hours.

After completion of the reaction, compound (I-e) can be isolated as a sulfide derivative, for example, by pouring the reaction mixture into water and extracting the resulting mixture with an organic solvent, followed by concentration. The isolated sulfide derivative (I-e) can be further purified by chromatography, recrystallization, or other similar methods, if necessary.

Compound (I-a) can be prepared according to a known synthetic method.

Examples of arthropod parasites with respect to which the compound of the present invention exerts a killing effect include harmful insects and harmful mites, and more specifically, the following arthropods.

Semi-winged bugs:

Delphacids (Delphacidae), such as the small dark cicadas ( Laodelphax striatellus ), brown rice cicadas ( Nilaparvata lugens ) and white-backed rice cicadas ( Sogatella furcifera ); cicadas (Deltocephalidae) such as green rice cicadas ( Nephotettix cincticeps ), green rice cicadas ( Nephotettix virescens ) and tea green cicadas ( Empoasca onukii ); aphids (Aphididae), such as aphids melon (Aphis gossypii), aphids green peach (Myzus persicae), aphid cabbage (Brevicoryne brassicae), aphids moth (Aphis spiraecola), aphid, potato leaf (Macrosiphum euphorbiae), aphids, potato vulgaris (Aulacorthum solani ), common cherry aphid ( Rhopalosiphum padi ), citrus aphid ( Toxoptera citricidus ) and plum powdery aphid ( Hyalopterus pruni ); shields (Pentatomidae), such as the bug-shield bug ( Nezara antennata ), bean bug bug ( Riptortus clavetus ), rice bug ( Leptocorisa chinensis ), white-spotted bug bug ( Eysarcoris parvus ) and shield bug ( Halyomorpha mista ); whiteflies (Aleyrodidae), such as greenhouse whiteflies ( Trialeurodes vaporariorum ), tobacco whiteflies ( Bemisia tabaci ), citrus whiteflies ( Dialeurodes citri ) and prickly white spiders ( Aleurocanthus spiniferus ); scale insects (Coccidae), such as Quadraspidiotus perniciosus red Wild orange (Aonidiella aurantii), Quadraspidiotus perniciosus California (Comstockaspis perniciosa), Quadraspidiotus perniciosus orange (Unaspis Citri), red wax Jose scale (Ceroplastes rubens), mealybug grooved Australian (Icerya purchasi), mealybug Japanese (Planococcus kraunhiae ), spiny mealybug ( Pseudococcus longispinis ) and mulberry scalefish ( Pseudaulacaspis Pentagona ); lace-bugs (Tingidae); bedbugs such as Cimex lectularius ; true leaf flies (Psyllidae); etc.

Lepidoptera:

Fireflies (Pyralidae), such as a stalk rice drill ( Chilo suppressalis ), a yellow rice drill ( Tryporyza incertulas ), a rice moth ( Cnaphalocrocis medinalis ), a cotton mullet ( Notarcha derogata ), a barn moth ( Plodia interpunctella corn ) ), the caterpillar of the Moth ( Hellula undalis ) and the caterpillar on the bluegrass ( Pediasia teterrellus ); scoops (Noctuidae), such as the Egyptian cotton scoop ( Spodoptera litura ), the small scoop ( Spodoptera exigua ), the camping worm ( Pseudaletia separata ), the cabbage camping worm ( Mamestra brassicae ), the ipsilon scoop ( Agrotis ipsilenidae ipsilonidae Plusilon) ), Thoricoplusia spp., Heliothis spp. and Helicoverpa spp .; whites (Pieridae) such as turnip whites ( Pieris rapae ); leafroller (Tortricidae), such as Adoxophyes spp., Tortrix eastern peach (Grapholita molesta), Tortrix soybean (Leguminivora glycinivorella), skorpionnik beans Asuka (Matsumuraeses azukivora), Tortrix mesh (Adoxophyes orana fasciata), tea leafroller small (Adoxophyes honmai.) , oriental tea leaf ( Homona magnanima ), apple leaf ( Archips fuscocupreanus ) and apple moth ( Cydia pomonella ); spotted moths (Gracillariidae), such as tea leafworm ( Caloptilia theivora ) and apple miner moth ( Phyllonorycter ringoneella ); carposinides such as a peach moth ( Carposina niponensis ); tiny moths (Lyonetiidae) such as Lyonetia spp .; bagpipes (Lymantriidae), such as Lymantria spp. and Euproctis spp .; ermine moths (Yponomeutidae), such as cabbage moth ( Plutella xylostella ); chamomile moths (Gelechiidae) such as pink boxworm ( Pectinophora gossypiella ) and tuberous moth tuber ( Phthorimaea operculella ); Bears and related species (Arctiidae), such as the caterpillar of the American white butterfly ( Hyphantria cunea ); true moths (Tineidae) such as moths ( Tinea translucens ) and furniture moths ( Tineola bisselliella ); etc.

Fringe-winged:

Thrips (Thripidae), such as yellow citrus thrips ( Frankliniella occidentalis ), melon thrips ( Thrips palmi ), yellow tea thrips ( Scirtothrips dorsalis ), onion thrips ( Thrips tabaci ), common thrips ( Frankliniella intonsa ), etc.

Diptera:

Mosquitoes such as Common Mosquito ( Culex pipiens pallens ), Cluex trita Seniorhynchus and Cluex quinquefasciatus ; mosquito species such as yellow fever mosquito (Aedes aegypti) and Asian tiger mosquito ( Aedes albopictus ); blood-sucking mosquitoes, such as Anopheles sinensis ; Jerky mosquitoes (Chironomidae); house flies (Muscidae), such as Musca domestica , and Muscina stabulans ; blue meat flies (Calliphoridae); gray meat flies (Sarcophagidae); small house flies (Fanniidae); flower girls (Anthomyiidae) such as cereal fly ( Delia platura ) and onion fly (Delia antiqua ); mined flies (Agromyzidae), such as rice Minira bead (Agromyza oryzae), rice undermines the small bead (Hydrellia griseola), tomato Minira fly (Liriomyza sativae), legume Minira fly (Liriomyza trifolii) and the pea Minira bead (Chromatomyia horticola); bread green-eyes (Chloropidae), such as rice stem larva of a fly (Chloro ps oryzae ); variegated wings (Tephritidae) such as melon fly ( Dacus cucurbitae ) and Mediterranean fruit fly ( Ceratitis Capitata ); Drosophila; humpbacks (Phoridae) such as Megaselia spiracularis ; butterflies (Psychodidae) such as Clogmia albipunctata ; midges; horseflies, such as horse horseflies ( Tabanus trigonus ); lighters, etc.

Coleoptera:

Corn root beetles ( Diabrotica spp.), Such as western corn root beetle ( Diabrotica virgifera ) and southern corn root beetle ( Diabrotica undecimpunctata howardi ); lamellar (Scarabaeidae), such as the May chafer beetle ( Anomala cuprea ), the soy beetle ( Anomala rufocuprea ) and the Japanese chrysanthemum ( Popillia japonica ); weevils such as maize weevil (Sitophilus zeamais), rice water weevil (Lissorhoptrus oryzophilus), boll weevil Asuka bean weevil (Callosobruchus chinensis), rice weevil (Echinocnemus squameus), boll weevil (Anthonomus grandis), and bouncing weevil (Sphenophorus venatus); darkling beetles (Tenebrionidae), such as the large mealworm ( Tenebrio molitor ) and chestnut worm ( Tribolium castaneum ); leaf beetles (Chrysomelidae), such as rice leaf beetle ( Oulema oryzae ), pumpkin leaf beetle ( Aulacophora femoralis ), striped flea ( Phyllotreta striolata ) and Colorado beetle ( Leptinotarsa decemlineata ); skin-eaters (Dermestidae), such as bark beetle ( Anthrenus verbasci ) and spotted skin- beetle ( Dermestes maculates ); grinders (Anobiidae), such as tobacco beetle ( Lasioderma serricorne ); ladybugs such as a 28-spotted potato bug ( Epilachna vigintioctopunctata ); bark beetles (Scolytidae) such as wood bite ( Lyctus brunneus ) and pine beetle ( Tomicus piniperda ); false beetles (Bostrychidae); pretenses (Ptinidae); lumberjacks (Cerambycidae), such as the white-spotted longhorn beetle ( Anoplophora malasiaca ); Nutcrackers ( Agriotes spp.); Paederus fuscipens , etc.

Orthoptera:

Asian Locust ( Locusta migratoria ), African Bear ( Gryllotalpa africana ), Short-winged Rice Filly ( Oxya yezoensis ), Japanese Rice Filly ( Oxya japonica ), Crickets, etc.

Fleas:

Cat flea ( Ctenocephalides felis ), dog flea ( Ctenocephalides canis ), human flea ( Pulex irritans ), southern rat flea ( Xenopsylla cheopis ), etc.

Lice

Large louse ( Pediculus humanus corporis ), pubic louse ( Phthirus pubis ), cattle louse short- haired blood-sucking ( Haematopinus eurysternus ), sheep louse ( Dalmalinia ovis ), pork louse ( Haematopinus suis ), etc.

Hymenoptera:

Ants (Formicidae), such as pharaoh ant ( Monomorium pharaosis ), black-brown forest ant ( Formica fusca japonica ), black house ant ( Ochetellus glaber ), Pristomyrmex pungens , Pheidole noda , leaf-cutting ant ( Acromyrmexpp . ( Solenopsis spp.); hornets (Vespidae); betilides (Betylidae); real sawflies (Tenthredinidae) such as the cabbage sawfly ( Athalia rosae ) and A thalia japonica , etc.

Cockroach:

Red cockroach ( Blattella germanica ), smoky brown cockroach ( Periplaneta fuliginosa ), American cockroach ( Periplaneta americana ), Periplaneta brunnea , black cockroach ( Blatta orientalis );

Termites:

Termites, such as Japanese underground termite ( Reticulitermes speratus ), Taiwanese underground termite ( Coptotermes formosanus ), western dry tree termite ( Incisitermes minor ), Daikoku dry tree termite ( Cryptotermes domesticus ), Odontotermes formosanus , Neotermes koshunensismes glymesmes , glyotimismes glyntesmslymsmes, glyntes glymes, gomensismes glyntesmslymsis glytms, gomes, gomes Glyptotermes fuscus, Glyptotermes kodamai, Glyptotermes kushimensis , Japanese raw wood termite (Hodotermopsis japonica), Coptotermes guangzhoensis, Reticulitermes miyatakei, Zheltonogov termite (Reticulitermes flavipes amamianus), Reticulitermes sp . , Nasutitermes takasagoesis , Pericapritermes nitobei and Sinocapritermes mushae, etc.

Ticks:

Spider mites (Tetranychidae), such as the two-spotted spider mite ( Tetranychus urticae ), the spider mite Kanzawa ( Tetranychus kanzawai ), the red citrus mite ( Panonychus citri ), the red fruit mite ( Panonychus ulchus spp. And Olmi ); gall mites (Eriophyidae), such as pink citrus gallic mite (Aculops pelekassi), Phyllocoptruta citri, tomato gallic mite (Aculops lycopersici), purple tea mite (Calacarus carinatus), pink tea gallic mite (Acaphylla theavagran), Eriophyes chibaensis, and mite Schlechtendahl ( Aculus schlechtendali ); mites (Tarsonemidae), such as transparent greenhouse mites ( Polyphagotarsonemus latus ); pseudopauntid mites such as Brevipalpus phoenicis ; tukerelidovye; ticks (Ixodidae), such as Haemaphysalis longicornis, Haemaphysalis flava, Dermacentor taiwanicus , ticks dog (Dermacentor variabilis), Ixodes ovatus, Ixodes persulcatus, tick dog black-footed (Ixodes scapularis), ticks kind Ambliommy (Amblyomma americanum), Boophilus microplus and Rhipicephalus sanguineus ; psoroptids, such as an ear tick ( Otodectes cynotis ); scabies mites (Sarcoptidae) such as Sarcoptes scabiei ; iron glands (Demodicidae), such as dog iron gland ( Demodex canis ); Acarides (Acaridae) such as mold mites ( Tyrophagus putrescentiae ) and Tyrophagus similis ; house dust mites (Pyroglyphidae) such as Dermatophagoides farinae and Dermatophagoides ptrenyssnus ; cheyletoid mites (Cheyletidae) such as Cheyletus eruditus , Cheyletus malaccensis and Cheyletus moorei ; parasitoid ticks (Dermanyssidae) such as tropical rat tick ( Ornithonyssus bacoti ), northern chicken tick ( Ornithonyssus sylviarum ) and red poultry tick ( Dermanyssus parasitoid gallinae ); thrombiculid ticks (Trombiculidae) such as Leptotrombidium akamushi ; arachnids (Araneae), such as the Japanese leafy spider ( Chiracanthium japonicum ), the red spider ( Latrodectus hasseltii ), etc.

Lepidopods: common flycatcher ( Thereuonema hilgendorfi ), Scolopendra subspinipes , etc .;

Two-legged: garden centipede ( Oxidus gracilis ), Nedyopus tambanus , etc .;

Isopods: common wood louse ( Armadillidium vulgare ), etc .;

Gastropods: Limax marginatus , Limax flavus , etc.

Although the pesticidal composition may be a compound of the present invention per se, the pesticidal composition of the present invention typically comprises a compound of the present invention in combination with a solid carrier, a liquid carrier and / or a gaseous carrier and, if necessary, a surfactant or other pharmaceutical additives, and takes the form of an emulsifiable concentrate, oil solution, shampoo, flowable composition, powder, wettable powder, granules, pastes, microcapsules, foams, aero Howard, gaseous form based on carbon dioxide, pills, gums, or similar shape. The pesticidal composition of the present invention can be processed into a poison bait, a mosquito coil, an electric mosquito plate, a fumigant pesticide, a fumigant or a sheet and then used.

The pesticidal composition of the present invention typically contains from 0.1 to 95% by weight of the compounds of the present invention.

Examples of solid carriers include finely ground powder or granules of clay (e.g. kaolin clay, diatomaceous earth, bentonite, Fubasami clay, acid clay, etc.), synthetic hydrated silica, talc, ceramic, and other inorganic materials (e.g. sericite, quartz, sulfur, activated carbon, calcium carbonate, hydrated silicon dioxide, etc.), chemical fertilizers (e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ammonium chloride, urea, etc.) and other similar substances.

Examples of a liquid carrier include aromatic or aliphatic hydrocarbons (e.g. xylene, toluene, alkylnaphthalene, phenylxylene ethane, kerosene, light oil, hexane, cyclohexane, etc.), halogenated hydrocarbons (e.g. chlorobenzene, dichloromethane, dichloroethane, trichloroethane, etc. .), alcohols (e.g. methanol, ethanol, isopropyl alcohol, butanol, hexanol, ethylene glycol, etc.), ethers (e.g. diethyl ether, ethylene glycol dimethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, monomethyl ether propylene glycol, tetrahydrofuran, dioxane, etc.), esters (e.g. ethyl acetate, butyl acetate, etc.), ketones (e.g. acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, etc.), nitriles (e.g. acetonitrile, isobutyronitrile, etc.), sulfoxides (e.g. dimethyl sulfoxide, etc.), acid amides (e.g. N, N-dimethylformamide, N, N-dimethylacetamide, etc.), vegetable oils (e.g. soybean oil, cottonseed oil, etc.), vegetable essential oils (e.g., orange oil, hyssop oil, lemon oil, etc.), water and others under other substances.

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

Examples of the surfactant include alkyl sulfate salts, alkyl sulfonate salts, alkyl aryl sulfonate salts, alkyl aryl ethers and their polyoxyethylated derivatives, polyethylene glycol ethers, polyhydric alcohol esters and sugar alcohol derivatives.

Examples of other pharmaceutical additives include a binder, dispersant, stabilizer and other similar substances, and specific examples thereof include casein, gelatin, polysaccharides (e.g. starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, saccharides, synthetic water-soluble polymers (e.g. polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acid, etc.), PAP (isopropyl acid phosphate), BHT (2,6-di-tert-butyl-4-methylphenol), BHA (mixture 2 tert-butyl-4-methoxyphenol and 3-t a-butyl-4-methoxyphenol), vegetable oils, mineral oils, fatty acids and fatty acid esters.

Examples of a base material for a resin preparation include vinyl chloride polymers, polyurethane and other similar polymers. A plasticizer such as phthalate (e.g. dimethyl phthalate, dioctyl phthalate, etc.), adipate, stearic acid and other similar substances can be added to the base material, if necessary. A resin-based composition is prepared by kneading a compound of the present invention in a base material using a conventional mixing apparatus followed by molding, for example, injection molding, extrusion molding, extrusion, or other similar methods. The resulting resin-based composition is molded in the form of a plate, film, tape, net, fiber or other similar form using an additional molding, cutting, or other similar steps, if necessary. Such resin preparations can be used, for example, in the form of a collar for an animal, earrings in an animal’s ear, a leaf, a leash or a garden stand.

Examples of a poison bait base material include grain powder, vegetable oil, sugar, crystalline cellulose, and the like. If necessary, an antioxidant, such as dibutylhydroxytoluene or nordihydroguyaretic acid, a preservative, such as dehydroacetic acid, a reagent that prevents children or pets from eating the product by mistake, such as hot pepper powder, a parasite-attracting flavoring agent, can be added to the base material, if necessary. as a substance with a smell of cheese, a substance with a smell of onions or peanut butter, or other similar substances.

The pesticidal composition of the present invention can be applied, for example, to arthropod parasites directly and / or to the place where the arthropod parasites live (for example, plants, animals, soil, etc.).

When using the pesticidal composition of the present invention to control parasites in agriculture and forestry, the amount applied is usually from 1 to 10,000 g / hectare, preferably from 10 to 500 g / hectare of active ingredient. When the pesticidal composition of the present invention is an emulsifiable concentrate, wettable powder, flowable form or microencapsulated form, it is usually used after dilution with water to have an active ingredient concentration of from 0.01 to 1000 ppm. When the pesticidal composition of the present invention is a powder or granule, it is usually used as such. The pesticidal composition of the present invention can be sprayed directly onto plants that are protected against arthropod parasites. Alternatively, the soil can be treated with the pesticidal composition of the present invention to control arthropod parasites living in the soil. The pesticidal composition of the present invention can also be processed beds before planting or holes for planting, or the base of the plant when planting. In addition, a leaf form of the pesticidal composition of the present invention can be applied by wrapping around plants, positioning near plants, laying on the surface of the soil at the base of the plant, or in a similar manner.

The pesticidal composition of the present invention can be applied to sown areas, such as cultivated land, rice fields, lawns and orchards. In some cases, the pesticidal composition of the present invention can destroy arthropod parasites in the sowing areas without harming crops grown in the sowing areas.

Examples of such crops are given below.

Crops: corn, rice, wheat, barley, rye, oats, sorghum, cotton, soy, peanuts, buckwheat, sugar beets, canola, sunflower, sugarcane, tobacco, etc .;

Vegetables: vegetables from the nightshade family (eggplant, tomato, green pepper, chilli, potatoes, etc.), vegetables from the pumpkin family (cucumber, pumpkin, zucchini, watermelon, melon, etc.), vegetables from the cruciferous family (Japanese radish, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage, black mustard, broccoli, cauliflower, etc.), vegetables from the Asteraceae family (burdock, edible chrysanthemum, artichoke, salad, etc.), vegetables from the lily family (onion-batun, onion, garlic, asparagus, etc.), vegetables from the umbrella family (carrots, parsley, celery, parsnip and etc.), vegetables from the haze family (spinach, beetroot, etc.), vegetables from the Labiaceae family (Japanese basil, mint, basil, etc.), strawberries, sweet potatoes, yams, aroid, etc. .d .;

Flowers and ornamental plants;

Deciduous plant;

Fruit plants: apple-shaped fruits (apple tree, common pear, sand pear, Chinese quince, quince, etc.), fruits with fleshy juicy pulp (peach, plum, nectarine, Japanese plum, cherry, apricot, home plum, etc. .), citrus fruits (mandarin, orange, lemon, lime, grapefruit, etc.), nuts (chestnut, walnut, hazelnuts, almonds, pistachios, cashew nuts, Australian nuts, etc.), berries (blueberries, cranberries, blackberries, raspberries, etc.), grapes, persimmons, olives, medlar, banana, coffee tree, dates, coconut, etc .;

Non-fruit plants: tea plant, mulberry, flowering trees and shrubs, street plants (ash, birch, dogwood, eucalyptus, ginkgo, lilac, maple, oak, poplar, scarlet, Chinese amber tree, plane tree, dzelkova, Japanese thuja , fir, tsuga broadleaf, solid juniper, pine, spruce, yew), etc.

The above crops include crops that have been given resistance to an HPPD inhibitor, such as isoxaflutol, an ALS inhibitor such as imazetapyr or tifensulfuron-methyl, an inhibitor of an enzyme that synthesizes EPSP, an inhibitor of an enzyme that synthesizes glutamine, using the classic selection method or genetic engineering method. an acetyl CoA carboxylase inhibitor or herbicide such as bromoxynil.

Examples of crops that have been stabilized using the classic selection method include Clearfield canola (registered trademark), which is resistant to imidazolinone-based herbicide, such as imazetapyr, and STS soy, which is resistant to ALS sulfonylurea inhibitor, such as like tifensulfuron methyl, and also SR corn, which is resistant to an acetyl CoA carboxylase inhibitor such as trion oxime herbicides or aryloxyphenoxypropionic acid herbicides lots. For example, a crop that has been given resistance to an acetyl CoA carboxylase inhibitor is described in Proc. Natl. Acad. Sci. USA, 1990, vol. 87, p. 7175-7179. In addition, an acetyl CoA carboxylase mutant that is resistant to an acetyl CoA carboxylase inhibitor is described in Weed Science, vol. 53, p.728-746, 2005. When a gene encoding an acetyl CoA carboxylase mutant is introduced into a crop using genetic engineering, or when a mutation associated with acetyl CoA carboxylase mutation is introduced into a gene encoding crop acetyl CoA carboxylase, a crop resistant to an acetyl CoA carboxylase inhibitor can be obtained. In addition, nucleic acids for introducing a base change mutation can be introduced into cells of a crop by chimeroplastics (see Gura T. 1999, Repairing the Genome's Spelling Mistakes, Science 285: 316-318) to induce a site-directed amino acid substitution mutation in a gene targeted at an acetyl CoA carboxylase inhibitor or crop herbicide, and thus a crop resistant to an acetyl CoA carboxylase inhibitor or herbicide can be obtained.

Examples of crops that have been stabilized by genetic engineering include maize cultivars that are resistant to glyphosate and glufosinate. Some of these corn cultivars are marketed under the brand name RoundupReady (registered trademark) and LibertyLink (registered trademark).

The above crops include crops that have been given genetic engineering ability to produce an insecticidal toxin, such as a selective toxin, which is known to be produced by a bacillus.

Examples of the insecticidal toxin that is produced by such a genetically engineered plant include insecticidal proteins derived from Bacillus cereus and Bacillus popilliae; δ-endotoxins derived from Bacillus thuringiensis, such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 and Cry9C; insecticidal proteins derived from Bacillus thuringiensis, such as VIP 1, VIP 2, VIP 3 and VIP 3A; insecticidal proteins derived from nematodes; toxins produced by animals, such as scorpion toxins, spider toxins, bee toxins and insect-specific nerve toxins; mushroom toxins; plant lectin; agglutinin; protease inhibitors such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin and papain inhibitors; ribosome inactivating proteins (RIP), such as ricin, maize-RIP, abrin, saporin and bryodin; steroid metabolizing enzymes such as 3-hydroxysteroid oxidase, ecdysteroid-UDP-glucosyl transferase and cholesterol oxidase; ecdysone inhibitors; HMG-COA reductase; ion channel inhibitors such as sodium channel inhibitors and calcium channel inhibitors; juvenile hormone esterase; diuretic hormone receptors; stilbene synthase; bibenzyl synthase; chitinase and glucanase.

The insecticidal toxin that is produced by such a genetically engineered plant also includes hybrid toxins of various insecticidal proteins, for example, δ-endotoxins, such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 and Cry9C, insect , VIP 2, VIP 3 and VIP 3A, and toxins in which some of the amino acids that make up the insecticidal protein are removed or modified. A hybrid toxin is obtained by combining various domains of insecticidal proteins by genetic engineering. An example of a toxin in which a portion of the amino acids constituting the insecticidal protein has been removed includes Cry1Ab in which a portion of the amino acids has been removed. An example of a toxin in which a portion of the amino acids constituting the insecticidal protein is modified includes a toxin in which one or more amino acids of a natural toxin are substituted.

An insecticidal toxin and a genetically engineered crop having the ability to produce an insecticidal toxin are described, for example, in EP-A-0374753, WO 93/07278, WO 95/34656, EP-A-0427529, EP-A-451878, WO 03 / 052073 and the like.

A genetically engineered crop with the ability to produce an insecticidal toxin, in particular, is resistant to attack by a winged insect, diptera, or lepidopteran.

Genetically engineered crops that have one or more insect resistant genes and therefore produce one or more insecticidal toxins are well known, and a number of them are commercially available. Examples of such genetically engineered plants include YieldGard (registered trademark) (corn cultivar expressing Cry1Ab toxin), YieldGard Rootworm (registered trademark) (corn cultivar expressing Cry3Bb1 toxin), YieldGard Plus (registered trademark) (corn cultivar expressing Cry1Ab and Cry3Bb1 toxins), Herculex I (registered trademark) (corn cultivar expressing the Cry1Fa2 toxin and phosphinotricin N-acetyltransferase (PAT) to confer resistance to glufosinate), NuCOTN33B (registered Trademark) (cotton cultivar expressing Cry1Ac toxin), Bollgard I (registered trademark) (cotton cultivar expressing Cry1Ac toxin), Bollgard II (registered trademark) (cotton cultivar expressing Cry1Ac and Cry2Ab toxin), VIPCOT (registered trademark) (cotton cultivar expressing VIP toxin), NewLeaf (registered trademark) (potato cultivar expressing Cry3A toxin), NatureGard Agrisure GT Advantage (registered trademark) (GA21 sign of glyphosate resistance), Agrisure CB Advantage (charge were detected trademark) (sign of Bt11 corn borer (CB)), Protecta (registered trademark) and the like.

The above crops include crops that have been given genetic engineering ability to produce an antipathogenic substance.

Examples of antipathogenic substances include PR proteins (PRP described in EP-A-0392225); ion channel inhibitors such as sodium channel inhibitors and calcium channel inhibitors (e.g., KP1, KP4, KP6 toxins, etc., produced by viruses); stilbene synthase; bibenzyl synthase; chitinase; glucanase; substances produced by microorganisms, such as peptide antibiotics, heterocycle-containing antibiotics, and protein factors influencing plant resistance to diseases (referred to as disease resistance genes of a plant and described in WO 03/000906); and other similar substances. Such anti-pathogenic substances and genetically engineered plants that produce anti-pathogenic substances are described in EP-A-0392225, WO 05/33818, EP-A-0353191 and the like.

When using the pesticidal composition of the present invention to combat the epidemic, the amount used is from 0.001 to 10 mg / m ^{3 of the} active ingredient when sprayed in space, and from 0.001 to 100 mg / m ^{2 of the} active ingredient when applied to a flat surface. The pesticidal composition in the form of an emulsifiable concentrate, wettable powder or in fluid form is usually used after dilution with water, so that the content of the active ingredient is from 0.001 to 10,000 ppm. The pesticidal composition in the form of an oil solution, an aerosol, a fumigating pesticide or a poison bait is usually used as such.

When using the pesticidal composition of the present invention to control external parasites of livestock, such as a cow, horse, pig, sheep, goat and chicken, or small animals, such as a dog, cat, rat and mouse, it can be applied to these animals when help known methods in veterinary medicine. In particular, in the proposed systemic control of harmful insects, the pesticidal composition of the present invention is administered, for example, in the form of a tablet, a mixture with food, a suppository or injection (for example, intramuscularly, subcutaneously, intravenously, intraperitoneally, etc.). In the alleged non-systemic control of harmful insects, the method of using the pesticidal composition of the present invention includes spraying the pesticidal composition, external processing or precisely directed processing of the pesticidal composition in the form of an oil solution or an aqueous liquid, washing the animal with a pesticidal composition in the form of shampoo, and attaching a collar or earring, made from a pesticidal composition in the form of a resin, to an animal. When administered to an animal, the amount of the compound of the present invention is usually from 0.1 to 1000 mg per 1 kg of animal body weight.

The pesticidal composition of the present invention can be used in a mixture or combination with other insecticides, nematicides, acaricides, fungicides, herbicides, plant growth regulators, synergists, fertilizers, soil improvers, animal feed and the like.

Examples of the active ingredient of such an insecticide include

(1) organophosphorus compounds:

acephate, aluminum phosphide, butathiophos, caduzafos, chlorethoxyphos, chlorfenvinphos, chlorpyrifos, chlorpyrifos-methyl, cyanophos (CYAP), diazinon, DCIP (dichlorodiisopropyl ether), dichlorofention (ECP), dichlorfos, DDVonfon, dvofonf, dvofonf, dvifonf, dvopon, dis, dvopon, dis ethion, etoprofos, etrimphos, fenthion (MPP), fenitrotion (MEP), fostiazate, formotion, hydrogen phosphorus, isofenfos, isoxathion, malathion, mesulfenfos, methidation (DMTP), monocrotophos, ice (BRP), oxideprofos (E) Fosalon, Phosmet (PMP), Pyrimifos-methyl, Pyridafenthion, Quinalphos, Phentoate (PAP), Profenophos, Propaf wasp, prothiophos, pyraclorphos, salithion, sulphrophos, tebufirimfos, temefos, tetrachlorvinphos, terboufos, thiometon, trichlorfon (DEP), vamidotion, forat, caduzafos and the like;

(2) carbamate compounds:

Alanicarb, Bendiocarb, Benfuracarb, BPMC, Carbaryl, Carbofuran, Carbosulfan, Cloethocarb, Ethiofencarb, Phenobarcarb, Phenothiocarb, Phenoxycarb, Furatiocarb, Isoprocarb (MIPC), Metarcarb, Methcarb, Methomel, Methylcarbyl, Oxycarbyl, Methylcarbyl, Oxycarbyl, Methylcarbyl, Oxycarbum, Methylcarbyl, Oxycarbum, Methylcarbyl, Oxycarbum, Methylcarbum, Methylcarbamide, Methylcarbamide, Methylcarbamide, Methylcarbamide, Methylcarbamide, Methomethylmethylene, thiodicarb, xylylcarb, aldicarb and the like;

(3) synthetic pyrethroid compounds:

acrinatrin, allethrin, benfluthrin, beta-cyfluthrin, bifentrin, cycloprotrin, cyfluthrin, cygalotrin, cypermethrin, empentrine, deltamethrin, esfenvalerate, etofenprox, fenpropatrin, fenvalerate, flufrinprin, flufrinprin, flufrinprin, flufrinprin, flufrinprin, Resmmetrin, sigma-cypermethrin, silafluofen, teflutrin, tralomethrin, transfluthrin, tetramethrin, phenotrin, cifenotrin, alpha-cypermethrin, zeta-cypermethrin, lambda-cygalotrin, gamma-cygalotrin, furametrin, tau-2,3-fluvalin, 6-tetrafluoro- 4-methylbenzyl 2,2-dimethyl-3- (1-propenyl) cyclopropanecarboxylate, 2,3,5,6-tetrafluoro-4- (methoxymethyl) benzyl 2,2-dimethyl-3- (2-methyl-1-propenyl ) cyclopropanecarboxylate, 2,3,5,6-tetrafluoro-4- (methoxymethyl) benzyl 2,2-dimethyl-3- (2-cyano-1-propenyl) cyclopropanecarboxylate, 2,3,5,6-tetrafluoro-4- (methoxymethyl) benzyl 2,2,3,3-tetramethylcyclopropanecarboxylate and the like;

(4) nereistoxin compounds:

cartap, bensultap, thiocyclam, monosultap, bisultap and the like;

(5) neonicotinoid compounds:

imidacloprid, nitenpyram, acetamipride, thiamethoxam, thiacloprid, dinotefuran, clothianidin and the like;

(6) benzoylurea compounds:

chlorofluazuron, bistrifluron, diafentyuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron, triazuron and the like;

(7) phenylpyrazole compounds:

acetoprol, etiprol, fipronil, vanilliprol, pyriprol, pyrafluprol and the like;

(8) Bt toxin insecticides:

live spores derived from crystalline toxins and crystalline toxins produced from Bacillus thuringiesis and mixtures thereof;

(9) hydrazine compounds:

chromafenoside, halofenoside, methoxyphenoside, tebufenoside and the like;

(10) organochlorine compounds:

aldrin, dieldrin, dinochlor, endosulfan, methoxychlor and the like;

(11) natural insecticides:

engine oil, nicotine sulfate and the like;

(12) other insecticides:

avermectin-B, bromopropylate, buprofesin, chlorfenapyr, cyromazine, DD (1,3-dichloropropene), emamectin-benzoate, phenazaquin, flupirazofos, hydroprene, methoprene, indoxacarb, methoxadiazone, milbemycin-A, pimethrosidipyridine, spiniridin, pirindrosipridine, spiniridin, pirindrosidir, pirindrosidir, pirindrosidir, pirindrosidir, pirindrosidir, pirindrosidir, pirindrosidir, pirindrosidir, pirindrosidir, pirindrosidir, pirindrosidir, pirindrosidir, pirindrosidir, pirindrosidir, pirindrosidir, pirindrosidir , tolfenpyrad, triazamate, flubendiamide, lepimectin, arsenic acid, benclothiaz, calcium cyanamide, calcium polysulfide, chlordane, DDT, DSP, flufenerim, flonamide, flurimfen, formometanate, metam ammonium trifenomerate, methamide oliphenebimen , sulfur, metaflumizone, alcohol Amat, pirifluhinazon, spinetoram, chlorantraniliprole, tralopiril, a compound represented by the following formula (A):

where X ^a1 is methyl, chloro, bromo or fluoro, X ^a2 is fluoro, chloro, bromo, C1-C4 haloalkyl or C1-C4 haloalkoxy, X ^a3 is fluoro, chloro or bromo, X ^a4 is optionally substituted C1-C4 alkyl optionally substituted C3-C4 alkenyl, optionally substituted C3-C4 alkynyl, optionally substituted C3-C5 cycloalkyl or hydrogen, X ^a5 is hydrogen or methyl, X ^a6 is hydrogen, fluoro or chloro, and X ^a7 is hydrogen, fluoro or chloro;

a compound represented by the following formula (B):

where X ^b1 is X ^b2 -NH-C (= O), X ^b2 -C (= O) -NH-CH ₂ , X ^b3 -S (O), optionally substituted pyrrol-1-yl, optionally substituted imidazole- 1-yl, optionally substituted pyrazol-1-yl, or optionally substituted 1,2,4-triazol-1-yl, X ^b2 is optionally substituted C1-C4 haloalkyl, such as 2,2,2-trifluoroethyl, or optionally substituted C3-C6 cycloalkyl, such as cyclopropyl, X ^b3 is optionally substituted C1-C4 alkyl, such as methyl, and X ^b4 is hydrogen, chloro, cyano or methyl;

a compound represented by the following formula (C):

where X ^c1 is optionally substituted C1-C4 alkyl, such as 3,3,3-trifluoropropyl, optionally substituted C1-C4 alkoxy, such as 2,2,2-trichloroethoxy, or optionally substituted phenyl, such as 4-cyanophenyl, or optionally substituted pyridyl, such as 2-chloro-3-pyridyl, X ^c2 is methyl or trifluoromethylthio, and X ^c3 is methyl or halogen; and similar substances.

Examples of active ingredient of the acaricide include atsekvinotsil, amitraz, benzoximate, bifenazate, brompropilat, chinomethionat, hlorbenzlat, CPCBS (hlorfenzon), clofentezine, tsiflumetofen, keltan (dicofol), etoxazole, fenbutatin oxide, fenothiocarb, fenpyroximate, fluakripirim, fluproksifen, hexythiazox, propargite ( BPPS), polynactins, pyridaben, pyrimidiphene, tebufenpyrad, tetradifon, spirodiclofen, spiromesifen, spiro tetramate, amidoflumet, cienopyrafen and the like.

Examples of the nematicide include DCIP, fostiazate, levamisole hydrochloride, methyl isothiocyanate, morantel tartrate, imitsiafos and the like.

Examples of the active ingredient of such a fungicide include strobilurin compounds such as azoxystrobin; organophosphate compounds such as tolclophos-methyl; azole compounds such as triflumisole, pefurazoate and diphenoconazole; phthalide, flutolanil, validamycin, probenazole, diclomesine, pencicuron, dazomet, kasugamycin, IBP, pyroquilone, oxolinic acid, tricyclazole, ferimzon, mepronil, EDDP, isoprothiolan, capropamide, diclocimet, furamoxyfiron, diramocitone, and flumeroxydione, diramocitone dihydrochlorothiophene, dimethylfiron, diplocimetrofen, and dimethoxydione.

Examples

Further, the present invention is explained in more detail using synthesis examples, preparation examples and test examples, but the present invention is not limited to the examples given.

The abbreviations used in this case have the following meanings. Me: methyl group, Et: ethyl group, Bn: benzyl group, Ph: phenyl group, Ts: p-toluenesulfonyl group, Ac: acetyl group.

First, examples of the synthesis of a compound of the present invention are given.

Synthesis Example 1

Stage 1-1

To a solution of 5.45 g of 1,4-dioxaspiro [4.5] decan-8-methanol in 30 ml of pyridine was added 6.64 g of p-toluenesulfonyl chloride and the mixture was stirred at room temperature for 6 hours. 100 ml of water was added to the reaction mixture, and then extracted twice with ethyl acetate. The organic layer was washed twice successively with 100 ml of 1 N. an aqueous solution of hydrochloric acid, once 100 ml of a saturated aqueous solution of sodium bicarbonate and once 100 ml of a saturated aqueous solution of sodium chloride. The organic layer was dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 9.86 g of 1,4-dioxaspiro [4.5] deca-8-ylmethyl-p-toluenesulfonate represented by the formula:

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.17-1.28 (2H, m), 1.43-1.57 (3H, m), 1.71-1 73 (4H, m), 2.45 (3H, s), 3.83 (2H, d), 3.88-3.95 (4H, m), 7.33 (2H, d), 7, 77 (2H, d).

Stage 1-2

To a solution of 9.86 g of 1,4-dioxaspiro [4.5] deca-8-ylmethyl-p-toluenesulfonate in 40 ml of dimethyl sulfoxide, 4.00 g of potassium thioacetate was added and the mixture was stirred at 70 ° C. for 8 hours. The reaction mixture was cooled to room temperature and 100 ml of water was added. The reaction mixture was extracted twice with 100 ml of ethyl acetate. The organic layer was washed with 100 ml of a saturated aqueous solution of sodium chloride, dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 5.41 g of 1,4-dioxaspiro [4.5] deca-8-ylmethylthioacetate represented by the formula:

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.29-1.36 (2H, m), 1.49-1.52 (3H, m), 1.73-1 80 (4H, m), 2.33 (3H, s), 2.82 (2H, d), 3.93 (4H, s).

Stage 1-3

To a solution of 5.41 g of 1,4-dioxaspiro [4.5] deca-8-ylmethylthioacetate in 20 ml of methanol was added 6.75 g of a 28% solution of sodium methylate in methanol at 0 ° C. under a nitrogen atmosphere. To the mixture was added 7.81 g of 3,3,3-trifluoro-1-iodopropane, the mixture was stirred at room temperature for 1 hour and then at 70 ° C for 1 hour. Then the reaction mixture was cooled to room temperature, 100 ml of water was added, and the mixture was concentrated under reduced pressure. The aqueous layer was extracted twice with 100 ml of ethyl acetate. The organic layer was washed with 100 ml of a saturated aqueous solution of sodium chloride, dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 3.69 g of 8- (3,3,3-trifluoropropylmethyl) -1,4-dioxaspiro [4.5] decane (hereinafter referred to as the present compound (1)) represented by the formula:

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.25-1.35 (2H, m), 1.48-1.58 (3H, m), 1.73-1 79 (2H, m), 1.84-1.88 (2H, m), 2.33-2.43 (2H, m), 2.46 (2H, d), 2.65-2.69 (2H, m), 3.94 (4H, s).

Synthesis Example 2

To a solution of 3.69 g of the present compound (1) in 60 ml of chloroform was added 6.56 g of m-chloroperbenzoic acid at 0 ° C, the mixture was stirred at room temperature for 1 hour and then at 50 ° C for 3 hours. The reaction mixture was cooled to 0 ° C and 50 ml of 5% aqueous sodium sulfite was added. Then the mixture was stirred for 1 hour, the organic layer was then separated. The aqueous layer was extracted with 50 ml of chloroform. The organic layers were combined, washed twice with 50 ml of a saturated aqueous solution of sodium bicarbonate and then 100 ml of a saturated aqueous solution of sodium chloride. The resulting organic layer was dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 4.10 g of 8- (3,3,3-trifluoropropylsulfonylmethyl) -1,4-dioxaspiro [4.5] decane (hereinafter referred to as the present compound (2)) represented by the formula:

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.43-1.53 (2H, m), 1.58-1.66 (2H, m), 1.73-1 79 (2H, m), 1.97-2.01 (2H, m), 2.15-2.17 (1H, m), 2.64-2.74 (2H, m), 2.95 (2H, d), 3.16-3.20 (2H, m), 3.92-3.97 (4H, m).

Synthesis Example 3

To a solution of 4.00 g of the present compound (2) in 30 ml of acetone was added 0.43 g of toluenesulfonic acid and the mixture was stirred at 50 ° C. for 8 hours under nitrogen. The reaction solution was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography to obtain 3.35 g of 4- (3,3,3-trifluoropropylsulfonylmethyl) cyclohexanone (hereinafter referred to as the present compound (3)) represented by the formula:

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.59-1.70 (2H, m), 2.33-2.36 (2H, m), 2.43-2 46 (4H, m), 2.58-2.67 (1H, m), 2.69-2.73 (2H, m), 3.03 (2H, d), 3.20-3.25 (2H, m).

Synthesis Example 4

To a solution of 0.82 g of the present compound (3) in 6 ml of chloroform, 1.06 g of diethylamino sulfur trifluoride was added at 0 ° C. under a nitrogen atmosphere, and the mixture was stirred at room temperature for 5 hours. The reaction solution was diluted with 30 ml of chloroform. 30 ml of water was added and the organic layer was separated. The aqueous layer was extracted twice with 30 ml of chloroform, the organic layers were combined and washed with 50 ml of a saturated aqueous solution of sodium chloride. The resulting organic layer was dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.30 g of 1,1-difluoro-4- (3,3,3, -trifluoropropylsulfonylmethyl) cyclohexanone (hereinafter referred to as the present compound (4)) and 0.27 g of 1-fluoro- 4- (3,3,3, -trifluoropropylsulfonylmethyl) cyclohexanone (hereinafter referred to as the present compound (5)), which are represented by the formulas:

The present compound (4)

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.45-1.56 (2H, m), 1.72-1.88 (2H, m), 2.05-2 23 (5H, m), 2.63-2.75 (2H, m), 2.97 (2H, d), 3.02-3.22 (2H, m).

The present compound (5)

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.65-1.73 (1H, m), 1.99-2.10 (2H, m), 2.19-2 25 (1H, m), 2.33-2.43 (3H, m), 2.63-2.75 (2H, m), 3.02 (2H, d), 3.18-3.22 (2H, m), 5.11-5.19 (1H, m).

Synthesis Example 5

To a solution of 0.83 g of the present compound (3) in 10 ml of tetrahydrofuran was added 7.2 ml of a 0.5M solution of ethynyl magnesium bromide in tetrahydrofuran at 0 ° C under nitrogen atmosphere and the mixture was stirred at 0 ° C for 5 hours. To the reaction solution was added 30 ml of 1 N. aqueous hydrochloric acid and the mixture was extracted twice with 30 ml of ethyl acetate. The organic layers were combined, washed with 30 ml of a saturated aqueous solution of sodium bicarbonate and 30 ml of a saturated aqueous solution of sodium chloride. The resulting organic layer was dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.43 g of 1-ethynyl-4- (3,3,3-trifluoropropylsulfonylmethyl) cyclohexanol (hereinafter referred to as the present compound (6)) represented by the formula:

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.50-1.59 (4H, m), 2.03-2.11 (6H, m), 2.53 (1H , s), 2.63-2.74 (2H, m), 2.97 (2H, d), 3.16-3.20 (2H, m).

Synthesis Example 6

To a solution of 0.29 g of the present compound (6) in 2 ml of chloroform, 0.32 g of diethylamino sulfur trifluoride was added at 0 ° C. under a nitrogen atmosphere, and the mixture was stirred at room temperature for 5 hours. The reaction solution was diluted with 20 ml of chloroform and 20 ml of water was added. Then the organic layer was separated. The aqueous layer was extracted twice with 20 ml of chloroform. The organic layers were combined and washed with 50 ml of a saturated aqueous solution of sodium chloride. The resulting organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.14 g of 1-ethenyl-1-fluoro-4- (3,3,3-trifluoropropylsulfonylmethyl) cyclohexane (hereinafter referred to as the present compound (7)) represented by the formula:

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.52-1.59 (2H, m), 1.72-1.94 (4H, m), 2.17-2 28 (3H, m), 2.62-2.72 (3H, m), 2.95 (2H, d), 3.17-3.22 (2H, m).

Synthesis Example 7

Stage 7-1

A solution of 4.86 g of diisopropylamine in 50 ml of tetrahydrofuran was cooled to −50 ° C. under a nitrogen atmosphere. To the solution was added 30 ml of a 1.6M solution of n-butyllithium / n-hexane and stirred at -50 ° C for 30 minutes. A solution of 9.28 g of methyl 2- (1,4-dioxaspiro [4.5] dec-8-yl) acetate in 40 ml of tetrahydrofuran was added dropwise to the solution over 15 minutes. The mixture was stirred at 0 ° C for 30 minutes and then cooled to -50 ° C. Then, 8.54 g of N-bromosuccinimide in 30 ml of tetrahydrofuran was added to the solution, the mixture was stirred at 0 ° C for 2 hours and then at room temperature for 5 hours. 100 ml of water was added to the reaction mixture, and the organic layer was separated. The aqueous layer was extracted twice with 100 ml of ethyl acetate. The organic layers were combined and washed twice with 100 ml of 1 N. an aqueous solution of hydrochloric acid, 100 ml of a saturated aqueous solution of sodium bicarbonate and 100 ml of a saturated aqueous solution of sodium chloride. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was dissolved in 50 ml of dimethyl sulfoxide. 5.04 g of potassium thioacetate was added and the mixture was stirred at 50 ° C for 4 hours. After cooling to room temperature, 100 ml of water was added to the reaction mixture, and then 100 ml of ethyl acetate was extracted twice. The organic layers were combined, washed with 100 ml of 1 N. an aqueous solution of hydrochloric acid, 100 ml of a saturated aqueous solution of sodium bicarbonate and 100 ml of a saturated aqueous solution of sodium chloride, dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 4.27 g of methyl 2- (acetylthio) -2- (1,4-dioxaspiro [4.5] dec-8-yl) acetate represented by the formula:

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.36-1.59 (4H, m), 1.65-1.81 (4H, m), 1.83-1 93 (1H, m), 2.33 (3H, s), 3.73 (3H, s), 3.93 (4H, s), 4.17 (1H, d).

Stage 7-2

To a solution of 4.27 g of methyl 2- (acetylthio) -2- (1,4-dioxaspiro [4.5] dec-8-yl) acetate in 30 ml of methanol was added 3.14 g of a 28% solution of sodium methylate in methanol at 0 ° C in an atmosphere of nitrogen. 4.31 g of 3,3,3-trifluoro-1-iodopropane was added to the mixture, the mixture was stirred at room temperature for 1 hour and then at 70 ° C for 1 hour. The reaction mixture was cooled to room temperature and 100 ml of water was added. The mixture was concentrated to a total amount of about 100 ml under reduced pressure, and then was extracted twice with 100 ml of ethyl acetate. The organic layers were combined, washed with 100 ml of a saturated aqueous solution of sodium chloride, dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 3.60 g of methyl 2- (1,4-dioxaspiro [4.5] dec-8-yl) -2- (3,3,3-trifluoropropylthio) acetate (hereinafter referred to as the present compound ( 8)) represented by the formula:

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.31-1.81 (8H, m), 2.11-2.16 (1H, m), 2.34-2 41 (2H, m), 2.71-2.78 (2H, m), 3.04 (1H, d), 3.75 (3H, s), 4.91-4.96 (4H, m )

Synthesis Example 8

To a solution of 3.60 g of the present compound (8) in 20 ml of chloroform, 4.75 g of m-chloroperbenzoic acid was added at 0 ° C. under a nitrogen atmosphere. The mixture was stirred at room temperature for 1 hour and then at 50 ° C for 3 hours. The reaction mixture was cooled to 0 ° C and 50 ml of 5% aqueous sodium sulfite was added. The mixture was stirred for 1 hour and the organic layer was then separated. The aqueous layer was extracted with 50 ml of chloroform, the organic layers were combined and washed twice with 50 ml of a saturated aqueous solution of sodium bicarbonate and 100 ml of a saturated aqueous solution of sodium chloride. The resulting organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 2.41 g of methyl 2- (1,4-dioxaspiro [4.5] dec-8-yl) -2- (3,3,3-trifluoropropylsulfonyl) acetate (hereinafter referred to as the present compound ( 9)) represented by the formula:

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.50-1.83 (7H, m), 2.14-2.17 (1H, m), 2.26-2 , 29 (1H, m), 2.66-2.74 (2H, m), 3.19-3.27 (1H, m), 3.48-3.53 (1H, m), 3.75 (1H, d), 3.84 (3H, s), 3.91-3.96 (4H, m).

Synthesis Example 9

0.11 g of toluenesulfonic acid was added to a solution of 2.41 g of the present compound (9) in 25 ml of acetone, and the mixture was stirred at 50 ° C. for 8 hours under a nitrogen atmosphere. The reaction mixture was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 1.24 g of methyl 2- (4-oxocyclohexyl) -2- (3,3,3-trifluoropropylsulfonyl) acetate (hereinafter referred to as the present compound (10)) represented by the formula:

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.73-1.86 (2H, m), 2.10-2.13 (1H, m), 2.40-2 49 (5H, m), 2.68-2.77 (3H, m), 3.28-3.35 (1H, m), 3.47-3.53 (1H, m), 3.85 (2H, d), 3.87 (3H, s).

Synthesis Example 10

To a solution of 1.24 g of the present compound (9) in 17 ml of chloroform, 1.37 g of diethylamino sulfur fluoride was added at 0 ° C. under a nitrogen atmosphere, and the mixture was stirred at room temperature for 5 hours. The reaction solution was diluted with 40 ml of chloroform and 30 ml of water was added thereto. The organic layer was then separated. The aqueous layer was extracted twice with 30 ml of chloroform. The organic layers were combined and washed with 50 ml of a saturated aqueous solution of sodium chloride. The resulting organic layer was dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.87 g of methyl 2- (4,4-difluorocyclohexyl) -2- (3,3,3-trifluoropropylsulfonyl) acetate (hereinafter referred to as the present compound (11)) represented by the formula:

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.67-1.83 (6H, m), 2.14-2.37 (3H, m), 2.66-2 74 (2H, m), 3.22-3.29 (1H, m), 3.45-3.52 (1H, m), 3.77 (1H, d), 3.86 (3H, s )

Synthesis Example 11

To a solution of 0.50 g of the present compound (11) in 5 ml of tetrahydrofuran was added 0.07 g of 60% sodium hydride at 0 ° C. under a nitrogen atmosphere. Then, 0.50 g of N-fluorobenzenesulfonimide was added thereto, and the mixture was stirred at room temperature for 5 hours. 30 ml of water was added to the reaction solution, and the organic layer was separated. The aqueous layer was extracted twice with 30 ml of ethyl acetate. The organic layers were combined and washed with 50 ml of a saturated aqueous solution of sodium chloride. The resulting organic layer was dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.43 g of methyl 2- (4,4-difluorocyclohexyl) -2-fluoro-2- (3,3,3-trifluoropropylsulfonyl) acetate (hereinafter referred to as the present compound (12)), represented by the formula:

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.67-1.89 (5H, m), 2.12-2.43 (3H, m), 2.55-2 74 (3H, m); 3.21-3.40 (2H, m); 3.98 (3H, s).

Synthesis Example 12

To a solution of 0.33 g of the present compound (12) in 3 ml of methanol was added 3 ml of a 2.0 M solution of ammonia in methanol at 0 ° C and the mixture was then stirred at room temperature for 18 hours. 30 ml of water was added to the reaction solution, and then 30 ml of ethyl acetate were extracted twice. The organic layers were combined and washed with 50 ml of a saturated aqueous solution of sodium chloride. The resulting organic layer was dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.43 g of 2- (4,4-difluorocyclohexyl) -2-fluoro-2- (3,3,3-trifluoropropylsulfonyl) acetamide (hereinafter referred to as the present compound (13)) represented by the formula:

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.73-1.88 (4H, m), 2.21-2.61 (4H, m), 2.61-2 77 (3H, m), 3.28-3.35 (1H, m), 3.40-3.48 (1H, m), 5.90 (1H, s), 6.53 (1H, s )

Synthesis Example 13

To a mixture of 22.8 g of cyclohexane-1,4-dimethanol monotosylate (trans / cis = 6/4) and 100 ml of dimethyl sulfoxide, 8.68 g of potassium thioacetate was added, the mixture was stirred at room temperature for 1 hour and then at 60 ° C within 6 hours. The mixture was then cooled to room temperature, 100 ml of a saturated aqueous solution of sodium chloride was added, and then 200 ml of tert-butyl methyl ether were extracted twice. The organic layers were combined, washed with 100 ml of a saturated aqueous solution of sodium chloride and 100 ml of water, dried over sodium sulfate, filtered and then concentrated under reduced pressure. 100 ml of methanol was added to the residue. While cooling in an ice bath, 28% dilution of 15.43 g of sodium methylate with 50 ml of methanol was added dropwise to the mixture over 30 minutes. The mixture was stirred for 30 minutes. To the mixture was added 17.92 g of 3,3,3-trifluoro-1-iodopropane and then stirred at 60 ° C for 6 hours. Then the reaction mixture was cooled to room temperature, 150 ml of a saturated aqueous solution of sodium chloride was added. Methanol was distilled off under reduced pressure. The resulting concentrate was extracted twice with 200 ml of tert-butyl methyl ether and subjected to silica gel column chromatography to obtain 8.46 g of 4- (3,3,3-trifluoropropylthiomethyl) cyclohexanemethanol (hereinafter referred to as the present compound (14)) represented by the formula:

.

.

The obtained present compound (14) was a mixture of trans form / cis form = 6/4.

Trans-4- (3,3,3-trifluoropropylthiomethyl) cyclohexanemethanol

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 0.96-1.01 (4H, m), 1.40-1.47 (4H, m), 1.58-1 83 (1H, m), 1.92-1.94 (1H, m), 2.34-2.40 (2H, m), 2.43 (2H, d), 2.64-2.68 (2H, m), 3.45 (2H, dd).

Cis-4- (3,3,3-trifluoropropylthiomethyl) cyclohexanemethanol

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.22-1.27 (4H, m), 1.40-1.62 (6H, m), 2.34-2 40 (2H, m), 2.52 (2H, d), 2.64-2.68 (2H, m), 3.53 (2H, dd).

Synthesis Example 14

To a solution of 7.4 g of the present compound (14) (trans form / cis form = 6/4) in 60 ml of chloroform was added 10.85 g of m-chloroperbenzoic acid at 0 ° C under nitrogen atmosphere, the mixture was stirred at room temperature for 1 hour and then at 50 ° C for 3 hours. The reaction mixture was cooled to 0 ° C and 50 ml of 5% aqueous sodium sulfite was added. The mixture was stirred for 1 hour. The organic layer was separated and the aqueous layer was extracted twice with 50 ml of chloroform. The organic layers were combined, washed twice with 50 ml of a saturated aqueous solution of sodium bicarbonate and 100 ml of a saturated aqueous solution of sodium chloride. The resulting organic layer was dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and then crystallized from tert-butyl methyl ether to obtain 4.13 g of the trans form (hereinafter referred to as the present compound (15t)) and 3.83 g of a cis form (hereinafter referred to as the present compound (15c)) 4- (3,3,3-trifluoropropylsulfonylmethyl) cyclohexanemethanol (hereinafter referred to as the present compound (15)) (trans form / cis form = 1/9) represented by the formula:

The present compound (15t)

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.04-1.19 (4H, m), 1.30 (1H, t), 1.45-1.49 (1H , m), 1.84-1.89 (2H, m), 2.04-2.10 (3H, m), 2.62-2.74 (2H, m), 2.93 (2H, d ), 3.15-3.19 (2H, m), 3.45 (2H, dd).

The present compound (15c)

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.04-1.19 (4H, m), 1.30 (1H, t), 1.45-1.49 (1H , m), 1.84-1.89 (2H, m), 2.04-2.10 (3H, m), 2.62-2.74 (2H, m), 2.93 (2H, d ), 3.15-3.19 (2H, m), 3.45 (2H, dd).

Synthesis Example 15

A solution of 7.46 g of oxalyl chloride in 50 ml of dichloromethane was cooled to −78 ° C. under a nitrogen atmosphere. A solution of 9.53 g of dimethyl sulfoxide in 50 ml of dichloromethane was added dropwise to the solution over 20 minutes, and the mixture was stirred at -50 ° C for 30 minutes. A solution of 13.51 g of the present compound (15t) in 150 ml of dichloromethane was added dropwise to the reaction mixture over 30 minutes, and then stirred at -50 ° C for 40 minutes. 15.70 g of triethylamine was added dropwise to the mixture over 40 minutes. The reaction mixture was stirred at room temperature for 18 hours. 100 ml of water was added to the reaction mixture, and the organic layer was separated, then 100 ml of chloroform was extracted twice. The organic layers were combined, washed successively with 150 ml of 1 N. an aqueous solution of hydrochloric acid, 150 ml of a saturated aqueous solution of sodium bicarbonate and 150 ml of water, dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 10.04 g of a trans form (hereinafter referred to as the present compound (16t)) of 4- (3,3,3-trifluoropropanesulfonylmethyl) cyclohexanecarbaldehyde (hereinafter referred to as the present compound (16)) represented by the formula:

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.18-1.27 (2H, m), 1.33-1.43 (2H, m), 2.06-2 24 (6H, m), 2.63-2.74 (2H, m), 2.95 (2H, d), 3.16-3.21 (2H, m), 9.62 (1H, s )

Synthesis Example 16

A solution of 23.21 g of carbon tetrabromide in 100 ml of dichloromethane was cooled to 0 ° C under nitrogen atmosphere and 36.72 g of triphenylphosphine was added to it over 30 minutes. The mixture was stirred for 30 minutes. A solution of 10.4 g of the present compound (16t) in 50 ml of dichloromethane was added dropwise to the solution over 30 minutes, and then stirred at room temperature for 6 hours. To the reaction mixture was added 150 ml of tert-butyl methyl ether. The solid was filtered off and the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 12.9 g of a trans form (hereinafter referred to as the present compound (17t)) 1- (2,2-dibromovinyl) -4- (3,3,3-trifluoropropylsulfonylmethyl) cyclohexane (hereinafter referred to as the present compound (17)) represented by the formula:

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.16-1.29 (4H, m), 1.84-1.86 (2H, m), 2.04-2 08 (2H, m), 2.21-2.26 (1H, m), 2.62-2.74 (2H, s), 2.92 (2H, d), 3.15-3.22 (2H, m), 6.19 (2H, d).

Synthesis Example 17

A solution of 12.90 g of the present compound (17t) and 60 ml of tetrahydrofuran were cooled to -78 ° C under a nitrogen atmosphere. A 1.6M n-butyllithium / n-hexane solution was added dropwise to the solution over 30 minutes, and the mixture was stirred at -50 ° C for 1 hour and then at 0 ° C for 2 hours. The reaction mixture was poured into 100 ml of 1 N. an aqueous solution of hydrochloric acid, which was cooled in an ice bath, was then extracted twice with 200 ml of tert-butyl methyl ether. The organic layers were combined, washed with 100 ml of a saturated aqueous solution of sodium bicarbonate and 100 ml of an aqueous saturated solution of sodium chloride, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 5.59 g of a trans form (hereinafter referred to as the present compound (18t)) 1-ethynyl-4- (3,3,3-trifluoropropylsulfonylmethyl) cyclohexane (hereinafter referred to as the present compound (18)) represented by the formula:

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.11-1.20 (2H, m), 1.43-1.53 (2H, m), 2.02-2 13 (6H, m), 2.19-2.23 (1H, m), 2.62-2.73 (2H, m), 2.91 (2H, d), 3.15-3.19 (2H, m).

Synthesis Example 17

Stage 17-1

A solution of 7.87 g of oxalyl chloride in 50 ml of dichloromethane was cooled to −78 ° C. under a nitrogen atmosphere. A solution of 4.85 g of dimethyl sulfoxide in 50 ml of dichloromethane was added dropwise to the solution over 20 minutes, and the mixture was stirred at -50 ° C for 30 minutes. To the reaction mixture was added dropwise a solution of 9.28 g of the present compound (15) (trans form / cis form = 6/4) in 150 ml of dichloromethane over 30 minutes and then stirred at -50 ° C for 40 minutes. 18.22 g of triethylamine was added dropwise over 40 minutes. The reaction mixture was stirred at room temperature for 18 hours. 100 ml of water was added to the reaction mixture, and the organic layer was separated, then 100 ml of chloroform was extracted twice. The organic layers were combined, washed successively with 150 ml of 1 N. an aqueous solution of hydrochloric acid, 150 ml of a saturated aqueous solution of sodium bicarbonate and 150 ml of water, dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 8.41 g of the present compound (16). The obtained present compound (16) was a mixture of trans form / cis form = 6/4.

Stage 17-2

A solution of 19.90 g of carbon tetrabromide in 100 ml of dichloromethane was cooled to 0 ° C in a nitrogen atmosphere. 31.48 g of triphenylphosphine was added over 30 minutes and the mixture was stirred for 30 minutes. To the solution was added a dropwise solution of 8.41 g of the present compound (16) (trans form / cis form = 6/4) in 50 ml of dichloromethane over 30 minutes and the mixture was stirred at room temperature for 6 hours. To the reaction mixture was added 150 ml of tert-butyl methyl ether. The solid was filtered off and the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 12.7 g of the present compound (17). The obtained present compound (17) was a mixture of trans form / cis form = 6/4.

Stage 17-3

A solution of 12.7 g of the present compound (17) (trans / cis = 6/4) in 60 ml of tetrahydrofuran was cooled to -78 ° C under a nitrogen atmosphere. 40 ml of a 1.6M solution of n-butyllithium in n-hexane was added dropwise to the solution over 30 minutes. The mixture was stirred at -50 ° C for 1 hour and then at 0 ° C for 2 hours. The reaction mixture was poured into 100 ml of 1 N. an aqueous solution of hydrochloric acid, which was cooled in an ice bath, was then extracted twice with 200 ml of n-butyl methyl ether. The organic layers were combined, washed with 100 ml of a saturated aqueous solution of sodium bicarbonate and 100 ml of a saturated aqueous solution of sodium chloride, dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 1.68 g of the cis form (hereinafter referred to as the present compound (18c)) of the present compound (18).

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.58-1.67 (2H, m), 1.82-1.84 (3H, m), 2.01-2 , 17 (5H, m), 2.62-2.74 (2H, m), 2.78 (1H, broad s), 2.97 (2H, d), 3.15-3.19 (2H , m).

Synthesis Example 18

A solution of 1.88 g of the present compound (17) in 10 ml of tetrahydrofuran was cooled to −78 ° C. under a nitrogen atmosphere. 2.8 ml of a 1.6M solution of n-butyllithium in n-hexane was added dropwise to the solution over 10 minutes, and the mixture was stirred at -50 ° C for 1 hour. 0.37 g of methyl acrylate was added and the mixture was stirred at 0 ° C for 2 hours. The reaction mixture was poured into 30 ml of 1 N. an aqueous solution of hydrochloric acid, which was cooled in an ice bath, was then extracted twice with 30 ml of tert-butyl methyl ether. The organic layers were combined, washed with 30 ml of a saturated aqueous solution of sodium bicarbonate and 30 ml of a saturated aqueous solution of sodium chloride, dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.70 g of 5- [4- (3,3,3-trifluoropropylsulfonylmethyl) cyclohexanyl] -4-valeric acid methyl ester (hereinafter referred to as the present compound (19)) represented by the formula:

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.14-1.20 (2H, m), 1.43-1.56 (2H, m), 2.02-2 22 (8H, m), 2.31-2.40 (2H, m), 2.54-2.60 (1H, m), 2.60-2.71 (1H, m), 2.89 -2.96 (3H, m), 3.24-3.26 (1H, m), 3.70 (3H, s).

Synthesis Example 19

To 0.57 g of the present compound (16), 0.32 g of pyridine and 0.14 g of hydroxylamine hydrochloride were added, and the mixture was stirred for 1 hour. To the mixture was added 1 ml of acetic anhydride and then stirred at 100 ° C for 2 hours. To the reaction mixture was added 30 ml of a saturated aqueous solution of sodium bicarbonate, then 30 ml of ethyl acetate were extracted twice. The organic layers were combined, washed with 30 ml of a saturated aqueous solution of sodium chloride, dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.32 g of 1-cyano-4- (3,3,3-trifluoropropylsulfonylmethyl) cyclohexane (hereinafter referred to as the present compound (20)) represented by the formula:

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.14-1.26 (2H, m), 1.63-1.73 (1H, m), 2.03-2 43 (7H, m), 2.64-2.74 (2H, m), 2.92 (2H, d), 3.16-3.20 (2H, m).

Synthesis Example 20

To a solution of 0.19 g of the present compound (3) in 1 ml of pyridine was added 0.08 g of O-methylhydroxylamine hydrochloride and the mixture was stirred at room temperature for 5 hours. 30 ml of water was added to the reaction solution, then 30 ml of ethyl acetate was extracted twice. The organic layers were combined and washed with 50 ml of a saturated aqueous solution of sodium chloride. The resulting organic layer was dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.19 g of 4- (3,3,3-trifluoropropylsulfonylmethyl) cyclohexanone O-methyloxy (hereinafter referred to as the present compound (21)) represented by the formula:

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.30-1.39 (2H, m), 1.84-1.92 (1H, m), 2.12-2 23 (3H, m), 2.37-2.46 (2H, m), 2.65-2.72 (2H, m), 2.96 (2H, d), 3.17-3.24 (2H, m).

Synthesis Example 21

To a solution of 0.58 g of the present compound (7) in 4 ml of tetrahydrofuran was added 2.2 ml of a 0.9M solution of methylmagnesium bromide in tetrahydrofuran at 0 ° C under nitrogen atmosphere and the mixture was stirred at room temperature for 5 hours. To the reaction solution was added 20 ml of water, then 20 ml of ethyl acetate was extracted. The organic layers were combined and washed with 50 ml of a saturated aqueous solution of sodium chloride. The resulting organic layer was dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.21 g of 1-ethynyl-4- (3,3,3-trifluoropropyl-1-sulfonylmethyl) cyclohexene (hereinafter referred to as the present compound (22)) represented by the formula:

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.47-1.61 (1H, m), 1.97-2.06 (2H, m), 2.24-2 30 (2H, m), 2.42-2.47 (2H, m), 2.65-2.75 (2H, m), 2.84 (1H, s), 3.00-3.03 (2H, m), 3.17-3.21 (2H, m), 6.14 (1H, br s).

Synthesis Example 22

A solution of 62.83 g of oxalyl chloride in 250 ml of dichloromethane was cooled to -78 ° C under nitrogen. A solution of 77.35 g of dimethyl sulfoxide in 250 ml of dichloromethane was added dropwise to the solution over 60 minutes, and the mixture was stirred at -50 ° C for 60 minutes. A solution of 84.54 g of the present compound (14) (trans-form / cis-form = 6/4) in 250 ml of dichloromethane was added dropwise to the reaction mixture, and then stirred at -50 ° C for 90 minutes. 100.18 g of triethylamine was added dropwise over 90 minutes. The reaction mixture was stirred at room temperature for 18 hours. 300 ml of water was added to the reaction mixture, and the organic layer was separated. The aqueous layer was then extracted twice with 200 ml of chloroform. The organic layers were combined, washed successively with 300 ml of 1 N. an aqueous solution of hydrochloric acid, 300 ml of a saturated aqueous solution of sodium bicarbonate and 300 ml of water, dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 23.03 g of the cis form (hereinafter referred to as the present compound (23c)) and 38.51 g of the trans form (hereinafter referred to as the present compound (23t)) 4- (3.3.3 trifluoropropylthiomethyl) cyclohexanecarbaldehyde (hereinafter referred to as the present compound (23)) represented by the formula:

.

.

The present compound (23c)

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.05-1.16 (2H, m), 1.49-1.66 (3H, m), 1.72-1 80 (2H, m), 2.07-2.16 (2H, m), 2.30-2.47 (5H, m), 2.63-2.67 (2H, m), 9.62 (1H, d).

The present compound (23t)

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 0.99-1.10 (2H, m), 1.24-1.34 (2H, m), 1.40-1 , 53 (1H, m), 1.97-2.08 (4H, m), 2.13-2.25 (1H, m), 2.31-2.43 (2H, m), 2.46 (2H, m), 2.65-2.69 (2H, m), 9.69 (1H, d).

Synthesis Example 23

A solution of 100.48 g of carbon tetrabromide in 300 ml of dichloromethane was cooled to 0 ° C. under a nitrogen atmosphere. 158.86 g of triphenylphosphine was added to it over 90 minutes. The mixture was stirred for 30 minutes. A solution of 38.51 g of the present compound (23t) in 100 ml of dichloromethane was added dropwise to the solution over 30 minutes, and the mixture was stirred at room temperature for 6 hours. To the reaction mixture was added 500 ml of tert-butyl methyl ether. The solid was filtered off and the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 66.56 g of a trans form (hereinafter referred to as the present compound (24t)) 1- (2,2-dibromovinyl) -4- (3,3,3-trifluoropropylthiomethyl) cyclohexane (hereinafter referred to as the present compound (24)) represented by the formula:

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 0.98-1.08 (2H, m), 1.10-1.20 (2H, m), 1.37-1 49 (1H, m), 1.78-1.85 (2H, m), 1.88-1.95 (2H, m), 2.17-2.29 (1H, m), 2.31 -2.41 (2H, m), 2.43 (2H, m), 2.64-2.68 (2H, m), 6.19 (1H, d).

Synthesis Example 24

A solution of 53.78 g of the present compound (24t) in 300 ml of tetrahydrofuran was cooled to −78 ° C. under a nitrogen atmosphere. To the solution was added dropwise 180 ml of a 1.6M solution of n-butyllithium in hexane over 60 minutes, the mixture was stirred at -50 ° C for 1 hour and then at 0 ° C for 2 hours. The reaction mixture was poured into 300 ml of 1 N. an aqueous solution of hydrochloric acid, which was cooled in an ice bath, was then extracted twice with 300 ml of tert-butyl methyl ether. The organic layers were combined, washed with 300 ml of a saturated aqueous solution of sodium bicarbonate and 300 ml of a saturated aqueous solution of sodium chloride, dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 31.54 g of a trans form (hereinafter referred to as the present compound (25t)) 1-ethynyl-4- (3,3,3-trifluoropropyl-1-sulfonylmethyl) cyclohexane (hereinafter referred to as the present compound (25)) represented by the formula:

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 0.92-1.03 (2H, m), 1.34-1.53 (3H, m), 1.86-1 94 (2H, m), 1.98-2.06 (3H, m), 2.15-2.24 (1H, m), 2.30-2.41 (2H, m), 2.42 (2H, d), 2.64-2.68 (2H, m).

Synthesis Example 25

The cis form of the present compound (25) (hereinafter referred to as the present compound (25c)) was obtained by the same procedure as in Synthesis Example 23 and Synthesis Example 24, except that the present compound (23c) was used instead of the present compound (23t).

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.38-1.53 (5H, m), 1.67-1.75 (2H, m), 1.78-1 86 (2H, m), 2.05 (1H, d), 2.31-2.44 (2H, m), 2.47 (2H, d), 2.65-2.69 (2H, m) ), 2.74-2.79 (1H, m).

Synthesis Example 26

To a suspension of 20.30 g of a double salt of 2KHSO ₅ · KHSO ₄ · K ₂ SO ₄ (Oxone, registered trademark) in 60 ml of water was added dropwise a solution of 7.51 g of the present compound (24t) in 60 ml of methanol over 60 minutes at -20 ° C in a nitrogen atmosphere. The mixture was stirred for 2 hours. 50 ml of a 10% aqueous solution of sodium sulfite were added to the reaction mixture, then 100 ml of ethyl acetate was extracted twice. The organic layers were combined, washed with 50 ml of a 10% aqueous solution of sodium sulfite and 50 ml of a saturated aqueous solution of sodium chloride, dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 4.88 g of a trans form (hereinafter referred to as the present compound (26t)) 1-ethynyl-4- (3,3,3-trifluoropropylsulfinylmethyl) cyclohexane (hereinafter referred to as the present compound (26)) represented by the formula:

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.02-1.21 (2H, m), 1.41-1.53 (2H, m), 1.82-2 , 00 (2H, m), 2.00-2.09 (4H, m), 2.20-2.27 (1H, m), 2.40-2.46 (1H, m), 2.57 -2.68 (2H, m), 2.71-2.92 (3H, m).

Synthesis Example 27

Stage 27-1

To a suspension of 7.35 g of potassium thioacetate in 30 ml of N-methyl-2-pyrrolidone was added dropwise 11.39 g of 3-bromo-1,1,1-trifluoropropane over 15 minutes at 0 ° C. under nitrogen and the mixture was stirred at room temperature for 1 hour. The reaction mixture was heated to 80 ° C, then distilled under reduced pressure to obtain 9.99 g of 3,3,3-trifluoropropylthioacetate represented by the formula:

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 2.35-2.43 (2H, m), 2.36 (3H, s), 3.01-3.06 (2H , m).

Using 3-iodo-1,1,1-trifluoropropane instead of 3-bromo-1,1,1-trifluoropropane, 3,3,3-trifluoropropylthioacetate are similarly prepared.

Stage 27-2

A solution of 9.99 g of 3.3,3-trifluoropropylthioacetate in 60 ml of tetrahydrofuran was cooled to 0 ° C. 11.2 g of a 28% solution of sodium methoxide in methanol were added dropwise thereto over 15 minutes and then stirred at room temperature for 1 hour. 4.38 g of chloroacetonitrile was added to the mixture at 0 ° C and then stirred at room temperature for 3 hours. The reaction vessel was cooled in an ice bath. An aqueous saturated sodium chloride solution was added to the reaction mixture, and the mixture was extracted twice with 100 ml of tert-butyl methyl ether. The organic layers were combined, washed with an aqueous saturated sodium chloride solution, dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 7.56 g of (3,3,3-trifluoropropylthio) acetonitrile represented by the formula:

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 2.44-2.55 (2H, m), 2.92-2.98 (2H, m), 3.36 (2H , from).

Stage 27-3

To a suspension of 4.97 g of (3,3,3-trifluoropropylthio) acetonitrile and 0.07 g of sodium tungstate dehydrate in 7 ml of water was added 2.3 ml of 31% aqueous hydrogen peroxide while stirring the suspension. In the middle of the reaction, a portion of the solids formed in the reaction solution were selected, purified by thin layer chromatography, and then ¹ H-NMR spectrum was taken to confirm the formation of (3,3,3-trifluoropropylsulfinyl) acetonitrile. The reaction mixture was heated to 65 ° C and 2.3 ml of 31% aqueous hydrogen peroxide was added. The mixture was stirred at 70 ° C for 1 hour and then cooled to room temperature. 5 ml of a 10% aqueous solution of sodium sulfite was added to the mixture, then 30 ml of ethyl acetate was extracted three times. The organic layers were combined, washed with an aqueous saturated sodium chloride solution, dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue was crystallized from chloroform: hexane = 1: 2 to give 5.44 g of (3,3,3-trifluoropropylsulfonyl) acetonitrile represented by the formula:

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 2.73-2.85 (2H, m), 3.50-3.56 (2H, m), 4.07 (2H , from).

(3,3,3-Trifluoropropylsulfinyl) acetonitrile:

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 2.66-2.73 (2H, m), 3.15-3.23 (2H, m), 3.67-3 81 (2H, m).

Stage 27-4

A mixture of 4.02 g of (3,3,3-trifluoropropylsulfonyl) acetonitrile, 100 ml of toluene, 0.23 g of DL-proline and 3.32 g of 1,4-cyclohexanedione monoethylene ketal was heated and stirred for 3 hours under reflux . Then 20 ml of toluene were distilled off, the reaction mixture was cooled to room temperature. 100 ml of tetrahydrofuran was added to the reaction mixture. The mixture was cooled to 0 ° C. and then 1.01 g of sodium borohydride was added. The mixture was stirred at room temperature for 6 hours and then cooled to 0 ° C. 100 ml of water and 100 ml of ethyl acetate were added. While stirring the reaction mixture, 100 ml of 1N was added dropwise. aqueous hydrochloric acid, then was extracted twice with 100 ml of ethyl acetate. The organic layer was washed with 100 ml of a saturated aqueous solution of sodium bicarbonate, 100 ml of a saturated aqueous solution of sodium chloride and 100 ml of water, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 5.45 g of 2- (1,4-dioxaspiro [4.5] dec-8-yl) -2- (3,3,3-trifluoropropylsulfonyl) acetonitrile (hereinafter referred to as the present compound (27 )) represented by the following formula (27).

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.61-1.90 (7H, m), 2.13-2.23 (1H, m), 2.39-2 51 (1H, m), 2.67-2.86 (2H, m), 3.39-3.47 (1H, m), 3.51-3.60 (1H, m), 3.85 (1H, d), 3.92-3.99 (4H, m).

Synthesis Example 28

A mixture of 3.20 g of the present compound (27), 7 ml of acetic acid and 3 ml of water was heated to 70 ° C and stirred for 10 hours. Then the reaction mixture was cooled to room temperature, 100 ml of ethyl acetate was added. The mixture was slowly added to 100 ml of a saturated aqueous sodium bicarbonate solution. The solution was stirred for 1 hour, then was extracted twice with 100 ml of ethyl acetate. The organic layers were combined, washed with 100 ml of a saturated aqueous solution of sodium bicarbonate and 100 ml of a saturated aqueous solution of sodium chloride, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 2.59 g of 2- (4-oxocyclohexyl) -2- (3,3,3-trifluoropropylsulfonyl) acetonitrile (hereinafter referred to as the present compound (28)) represented by the formula:

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.87-1.97 (2H, m), 2.18-2.25 (1H, m), 2.42-2 60 (5H, m), 2.73-2.95 (3H, m), 3.41-3.51 (1H, m), 3.55-3.66 (1H, m), 3.97 (1H, d).

Synthesis Example 29

To a solution of 0.15 g of the present compound (28) in 5 ml of dichloromethane, 0.21 g of diethylamino sulfur trifluoride was added at -20 ° C under a nitrogen atmosphere. The mixture was stirred at room temperature for 5 hours. The reaction solution was diluted with 30 ml of chloroform. 30 ml of water was added to it and the organic layer was separated. The aqueous layer was extracted twice with 30 ml of chloroform, the organic layers were combined and washed with 50 ml of a saturated aqueous solution of sodium chloride. The resulting organic layer was dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.16 g of 2- (4,4-difluorocyclohexyl) -2- (3,3,3-trifluoropropylsulfonyl) acetonitrile (hereinafter referred to as the present compound (29)) represented by the formula:

.

.

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.41-1.99 (5H, m), 2.16-2.32 (3H, m), 2.42-2 58 (1H, m), 2.70-2.86 (2H, m), 3.38-3.49 (1H, m), 3.54-3.68 (1H, m), 3.87 (1H, d)

Synthesis Example 30

To a solution of 1.49 g of the present compound (28) in 20 ml of tetrahydrofuran was added 30 ml of a 0.5M solution of ethynyl magnesium bromide in tetrahydrofuran at 0 ° C under nitrogen atmosphere and the mixture was stirred at 0 ° C for 5 hours. 50 ml of 1N was added to the reaction solution. an aqueous solution of hydrochloric acid, then was extracted twice with 50 ml of ethyl acetate. The organic layers were combined and washed with 50 ml of a saturated aqueous solution of sodium bicarbonate and 50 ml of a saturated aqueous solution of sodium chloride. The resulting organic layer was dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 1.69 g of 2- (4-ethynyl-4-hydroxycyclohexyl) -2- (3,3,3-trifluoropropylsulfonyl) acetonitrile (hereinafter referred to as the present compound (30)) represented by the formula:

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.59-2.28 (9H, m), 2.28-2.47 (1H, m), 2.61 (1H , s), 2.71-2.84 (2H, m), 3.40-3.48 (1H, m), 3.52-3.60 (1H, m), 3.87 (1H, d )

Synthesis Example 31

To a solution of 0.65 g of the present compound (30) in 6 ml of dichloromethane was added 0.48 g of diethylamino sulfur trifluoride at 0 ° C. under a nitrogen atmosphere, and the mixture was stirred at room temperature for 5 hours. The reaction solution was diluted with 20 ml of chloroform. 20 ml of water was added to it and the organic layer was separated. The aqueous layer was extracted twice with 20 ml of chloroform. The organic layers were combined and washed with 50 ml of a saturated aqueous solution of sodium chloride. The resulting organic layer was dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.31 g of 2- (4-ethynyl-4-fluorocyclohexyl) -2- (3,3,3-trifluoropropylsulfonyl) acetonitrile (hereinafter referred to as the present compound (31)) and 0.23 g 2- (4-ethynylcyclohexen-3-yl) -2- (3,3,3-trifluoropropylsulfonyl) acetonitrile (hereinafter referred to as the present compound (32)), which are represented by the formulas:

The resulting present compound (32) was a 1: 1 mixture of isomers.

The present compound (31)

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.73-2.15 (6H, m), 2.25-2.39 (2H, m), 2.44-2 54 (1H, m), 2.66 (1H, d), 2.71-2.84 (2H, m), 3.40-3.48 (1H, m), 3.53-3.61 (1H, m), 3.87 (1H, d).

The present compound (32)

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.68-2.84 (9H, m), 2.84 (1H, d), 3.39-3.49 (1H , m), 3.51-3.66 (1H, m), 3.89 (1H, d), 6.10-6.18 (2H, m).

Synthesis Example 32

To a solution of 2.81 g of the present compound (28) in 10 ml of tetrahydrofuran was added 0.75 g of pyridine and 0.79 g of methoxyamine hydrochloride, and the mixture was stirred at room temperature for 3 hours. To the reaction solution was added 30 ml of 1 N. an aqueous solution of hydrochloric acid, then was extracted twice with 50 ml of ethyl acetate. The organic layers were combined, washed with 50 ml of a saturated aqueous solution of sodium bicarbonate and 50 ml of a saturated aqueous solution of sodium chloride. The resulting organic layer was dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 2.86 g of 2- [4- (methoxyimino) cyclohexyl] -2- (3,3,3-trifluoropropylsulfonyl) acetonitrile (hereinafter referred to as the present compound (33)) represented by the formula:

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.50-1.71 (2H, m), 1.80-1.91 (1H, m), 1.95-2 , 08 (1H, m), 2.16-2.27 (1H, m), 2.30-2.44 (1H, m), 2.49-2.57 (1H, m), 2.62 -2.71 (1H, m), 2.72-2.86 (2H, m), 3.32-3.48 (2H, m), 3.52-3.61 (1H, m), 3 83 (3H, s); 3.87 (1H, d).

Synthesis Example 33

To a solution of 0.20 g of the present compound (28) in 2 ml of pyridine was added 0.06 g of hydroxylamine hydrochloride and the mixture was stirred at room temperature for 3 hours. 50 ml of hexane was added to the reaction solution, then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.093 g of 2- [4- (hydroxyimino) cyclohexyl] -2- (3,3,3-trifluoropropylsulfonyl) acetonitrile (hereinafter referred to as the present compound (34)) represented by the formula:

¹ H-NMR (CD ₃ OD, TMS, δ (ppm)): 1.29-1.48 (2H, m), 1.69-1.85 (1H, m), 1.87- 2.01 (1H, m), 2.07-2.27 (2H, m), 2.29-2.38 (1H, m), 2.51-2.59 (1H, m), 2, 67-2.81 (2H, m), 3.18-3.22 (1H, m), 3.26-3.34 (2H, m), 4.47 (1H, br s).

Synthesis Example 34

According to the procedure of Synthesis Example 33, except that instead of using hydroxylamine hydrochloride, 0.008 g of ethoxyamine hydrochloride was used, 0.095 g of 2- [4- (ethoxyimino) cyclohexyl] -2- (3,3,3-trifluoropropylsulfonyl) acetonitrile (hereinafter referred to as the present) was obtained compound (35)) represented by the formula:

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.25 (3H, t), 1.51-1.72 (2H, m), 1.79-1.92 (1H , m), 1.95-2.07 (1H, m), 2.17-2.27 (1H, m), 2.31-2.43 (1H, m), 2.49-2.59 (1H, m), 2.61-2.71 (1H, m), 2.72-2.86 (2H, m), 3.35-3.49 (2H, m), 3.51-3 61 (1H, m); 3.85 (1H, d); 4.05 (2H, q).

Synthesis Example 35

According to the procedure of Synthesis Example 33, except that 0.01 g of tert-butoxyamine hydrochloride was used instead of hydroxylamine hydrochloride, 0.19 g of 2- [4- (tert-butoxyimino) cyclohexyl] -2- (3.3.3 trifluoropropylsulfonyl) acetonitrile (hereinafter referred to as the present compound (36)) represented by the formula:

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.26 (9H, s), 1.49-1.70 (2H, m), 1.75-1.88 (1H , m), 1.91-2.06 (1H, m), 2.14-2.25 (1H, m), 2.27-2.42 (1H, m), 2.51-2.59 (1H, m), 2.59-2.70 (1H, m), 2.71-2.88 (2H, m), 3.35-3.48 (2H, m), 3.52-3 68 (1H, m); 3.86-3.88 (1H, m).

Synthesis Example 36

According to the procedure of Synthesis Example 33, except that instead of using hydroxylamine hydrochloride, 0.009 g of O-allylhydroxylamine hydrochloride was used, 0.061 g of 2- [4- (O-allylhydroxylimino) cyclohexyl] -2- (3,3,3-trifluoropropylsulfonyl) acetonitrile was obtained (hereinafter referred to as the present compound (37)) represented by the formula:

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.52-1.72 (2H, m), 1.79-1.94 (1H, m), 1.96-2 09 (1H, m), 2.16-2.28 (1H, m), 2.31-2.42 (1H, m), 2.50-2.59 (1H, m), 2.61 -2.72 (1H, m), 2.72-2.86 (2H, m), 3.38-3.48 (2H, m), 3.52-3.61 (1H, m), 3 , 85-3.88 (1H, m), 4.52-4.55 (2H, m), 5.19-5.33 (2H, m), 5.92-6.04 (2H, m) .

Synthesis Example 37

According to the procedure of Synthesis Example 33, except that instead of using hydroxylamine hydrochloride, 0.009 g of O-benzylhydroxylamine hydrochloride was used, 0.10 g of 2- [4- (O-benzylhydroxylimino) cyclohexyl] -2- (3,3,3-trifluoropropylsulfonyl) was obtained ) acetonitrile (hereinafter referred to as the present compound (38)) represented by the formula:

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.49-1.72 (2H, m), 1.81-2.08 (2H, m), 2.16-2 27 (1H, m), 2.30-2.43 (1H, m), 2.50-2.58 (1H, m), 2.61-2.70 (1H, m), 2.72 -2.83 (2H, m), 3.38-3.48 (2H, m), 3.51-3.61 (1H, m), 3.84-3.87 (1H, m), 5 07 (2H, s), 7.28-7.34 (1H, m), 7.35-7.36 (4H, m).

Synthesis Example 38

To a solution of 0.20 g of the present compound (28) in 2 ml of pyridine, 0.06 g of O-carboxymethylhydroxylamine hydrochloride was added and the mixture was stirred at room temperature for 3 hours. To the reaction solution was added 30 ml of 1 N. an aqueous solution of hydrochloric acid, then was extracted twice with 30 ml of ethyl acetate. The resulting organic layer was dried over sodium chloride, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.094 g of 2- [4- (O-carboxymethylhydroxylimine) cyclohexyl] -2- (3,3,3-trifluoropropylsulfonyl) acetonitrile (hereinafter referred to as the present compound (39)) represented by the formula:

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.56-1.72 (2H, m), 1.88-2.11 (2H, m), 2.17-2 , 29 (1H, m), 2.31-2.43 (1H, m), 2.47-2.56 (1H, m), 2.60-2.70 (1H, m), 2.73 -2.84 (2H, m), 3.38-3.43 (4H, m), 4.57 (2H, s).

Synthesis Example 39

A solution of 0.16 g of the present compound (33) in 3 ml of dimethyl sulfoxide was cooled to 0 ° C. under a nitrogen atmosphere. 0.05 g of a dispersion of 60% sodium hydride in liquid paraffin was added to the mixture, and the mixture was stirred for 30 minutes. 0.11 g of methyl iodide was added and the mixture was stirred at room temperature overnight. 10 ml of 1N was added to the reaction solution. an aqueous solution of hydrochloric acid, then was extracted twice with 30 ml of ethyl acetate. The organic layers were combined and washed with 10 ml of a saturated aqueous solution of sodium bicarbonate and 10 ml of a saturated aqueous solution of sodium chloride. The resulting organic layer was dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.13 g of 2- [4- (methoxyimino) cyclohexyl] -2- (3,3,3-trifluoropropylsulfonyl) propionitrile (hereinafter referred to as the present compound (40)) represented by the formula:

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.31-1.64 (2H, m), 1.75 (3H, s), 1.76-1.91 (1H , m), 2.13-2.32 (3H, m), 2.48-2.62 (2H, m), 2.69-2.87 (2H, m), 3.32-3.47 (2H, m), 3.55-3.64 (1H, m), 3.83 (3H, s).

Synthesis Example 40

According to the procedure of Synthesis Example 39, except that 0.13 g of ethyl iodide was used instead of methyl iodide, 0.13 g of 2- [4- (methoxyimino) cyclohexyl] -2- (3,3,3-trifluoropropylsulfonyl) butyronitrile (further called the present compound (41)) represented by the formula:

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.27 (3H, t), 1.43-1.69 (2H, m), 1.73-1.87 (1H , m), 2.10-2.31 (5H, m), 2.49-2.61 (2H, m), 2.71-2.87 (2H, m), 3.33-3.47 (2H, m), 3.55-3.66 (1H, m), 3.83 (3H, s).

Synthesis Example 41

According to the method of Synthesis Example 39, except that 0.14 g of 1-iodopropane was used instead of methyl iodide, 0.055 g of 2- [4- (methoxyimino) cyclohexyl] -2- (3,3,3-trifluoropropylsulfonyl) pentannitrile (further called the present compound (42)) represented by the formula:

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.06 (3H, t), 1.44-1.71 (4H, m), 1.73-1.86 (1H , m), 1.94-2.13 (2H, m), 2.15-2.31 (3H, m), 2.48-2.61 (2H, m), 2.73-2.83 (2H, m), 3.32-3.46 (2H, m), 3.55-3.65 (1H, m), 3.83 (3H, s).

Synthesis Example 42

According to the procedure of Synthesis Example 39, except that 0.10 g of 3-bromopropane was used instead of methyl iodide, 0.14 g of 2- [4- (methoxyimino) cyclohexyl] -3-methyl-2- (3.3.3 -trifluoropropylsulfonyl) -4-pentenonitrile (hereinafter referred to as the present compound (43)) represented by the formula:

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.41-1.68 (2H, m), 1.73-1.87 (1H, m), 2.12-2 , 33 (3H, m), 2.47-2.82 (5H, m), 2.86-2.91 (1H, m), 3.31-3.48 (2H, m), 3.61 -3.68 (1H, m), 3.83 (3H, s), 5.40-5.49 (2H, m), 5.87-6.02 (1H, m).

Synthesis Example 43

According to the procedure of Synthesis Example 39, except that 0.10 g of 3-bromopropane was used instead of methyl iodide, 0.14 g of 2- [4- (methoxyimino) cyclohexyl] -3-methyl-2- (3.3.3 -trifluoropropylsulfonyl) -4-pentynnitrile (hereinafter referred to as the present compound (44)) represented by the formula:

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.29-1.47 (1H, m), 1.50-1.68 (1H, m), 1.74-1 , 91 (1H, m), 2.13-2.35 (3H, m), 2.43-2.45 (1H, m), 2.49-2.61 (1H, m), 2.73 -2.86 (3H, m), 2.91-3.11 (2H, m), 3.32-3.47 (1H, m), 3.73-3.89 (2H, m), 3 83 (3H, s).

Synthesis Example 44

A solution of 0.45 g of the present compound (33) in 5 ml of tetrahydrofuran was cooled to 0 ° C in a nitrogen atmosphere. 0.10 g of a dispersion of 60% sodium hydride in liquid paraffin was added thereto, and the mixture was stirred for 30 minutes. Then, 0.20 g of N-chlorosuccinimide was added and the mixture was stirred at room temperature overnight. 10 ml of 1N was added to the reaction solution. an aqueous solution of hydrochloric acid, then was extracted twice with 30 ml of ethyl acetate. The organic layers were combined, washed with 10 ml of a saturated aqueous solution of sodium bicarbonate and 10 ml of a saturated aqueous solution of sodium chloride. The resulting organic layer was dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.39 g of 2-chloro-2- [4- (methoxyimino) cyclohexyl] -2- (3,3,3-trifluoropropylsulfonyl) acetonitrile (hereinafter referred to as the present compound (45)), represented by the formula:

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.52-1.91 (3H, m), 2.16-2.29 (1H, m), 2.34-2 48 (2H, m), 2.52-2.63 (1H, m), 2.74-2.89 (3H, m), 3.36-3.46 (1H, m), 3.64 -3.82 (2H, m); 3.84 (3H, s).

Synthesis Example 45

A mixture of 1.00 g of (3,3,3-trifluoropropylsulfonyl) acetonitrile, 30 ml of tetrahydrofuran, 0.12 g of DL-proline and 1.01 g of cyclopentanone was heated and stirred for 6 hours under reflux. The reaction mixture was cooled to 0 ° C. and 0.42 g of sodium borohydride was added. The mixture was stirred at room temperature for 6 hours. Then the reaction mixture was cooled to 0 ° C, 10 ml of water and 30 ml of ethyl acetate were added. With stirring, 50 ml of 1N was added dropwise to the mixture. hydrochloric acid, then was extracted twice with 30 ml of ethyl acetate. The organic layers were combined, washed successively with 30 ml of a saturated aqueous solution of sodium bicarbonate and 30 ml of a saturated aqueous solution of sodium chloride, dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 1.01 g of 2-cyclopentyl-2- (3,3,3-trifluoropropylsulfonyl) acetonitrile (referred to as the present compound (46)) represented by the following formula (46).

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.46-1.56 (1H, m), 1.59-1.71 (3H, m), 1.73-1 85 (2H, m), 2.02-2.17 (2H, m), 2.66-2.86 (3H, m), 3.38-3.56 (2H, m), 4.03 (1H, d).

Synthesis Example 46

According to the procedure of Synthesis Example 45, except that 1.14 g of cyclohexanone was used instead of cyclopentanone, 1.01 g of 2-cyclohexyl-2- (3,3,3-trifluoropropylsulfonyl) acetonitrile (hereinafter referred to as the present compound (47)) was obtained represented by the following formula (47).

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.16-1.28 (1H, m), 1.30-1.47 (4H, m), 1.69-1 77 (1H, m), 1.79-1.88 (3H, m), 2.15-2.22 (1H, m), 2.39-2.49 (1H, m), 2.70 -2.84 (2H, m), 3.37-3.46 (1H, m), 3.48-3.56 (1H, m), 3.80 (1H, d).

Synthesis Example 47

According to the procedure of Synthesis Example 45, except that 1.23 g of cycloheptanone was used instead of cyclopentanone, 1.24 g of 2-cyclohexyl-2- (3,3,3-trifluoropropylsulfonyl) acetonitrile (hereinafter referred to as the present compound (48)) was obtained represented by the following formula (48).

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.50-1.86 (11H, m), 2.14-2.22 (1H, m), 2.56-2 62 (1H, m), 2.70-2.83 (2H, m), 3.36-3.44 (1H, m), 3.48-3.56 (1H, m), 3.84 (1H, d).

Synthesis Example 48

According to the procedure of Synthesis Example 45, except that 1.34 g of 4-methylcyclohexanone was used instead of cyclopentanone, 1.12 g of 2- (4-methylcyclohexyl) -2- (3,3,3-trifluoropropylsulfonyl) acetonitrile (hereinafter referred to as the present compound (49)) represented by the following formula (49). The obtained present compound (49) was a mixture of isomers 6/4.

The main isomer of the present compound (49):

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 0.98 (3H, d), 1.00-1.12 (1H, m), 1.32-1.97 (8H , m), 2.45-2.54 (1H, m), 2.71-2.87 (2H, m), 3.37-3.59 (2H, m), 3.92 (1H, d )

Side isomer of the present compound (49):

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 0.91 (3H, d), 1.32-1.97 (8H, m), 2.14-2.23 (1H , m), 2.33-2.43 (1H, m), 2.71-2.87 (2H, m), 3.37-3.59 (2H, m), 3.82 (1H, d )

Synthesis Example 49

According to the procedure of Synthesis Example 45, except that instead of cyclopentanone 1.24 g of 4,4-dimethylcyclohexanone was used, 0.98 g of 2- (4,4-dimethylcyclohexyl) -2- (3,3,3-trifluoropropylsulfonyl) was obtained acetonitrile (hereinafter referred to as the present compound (50)) represented by the following formula (50).

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 0.93 (3H, s), 0.94 (3H, s), 1.25-1.36 (2H, m), 1.45-1.69 (5H, m), 1.94-2.03 (1H, m), 2.30-2.39 (1H, m), 2.69-2.83 (2H, m) ), 3.37-3.46 (1H, m), 3.48-3.56 (1H, m), 3.84 (1H, d).

Synthesis Example 50

A mixture of 3.31 g of (3,3,3-trifluoropropylsulfonyl) acetonitrile, 60 ml of tetrahydrofuran, 0.19 g of DL-proline and 2.03 g of 4-cyanocyclohexanone was heated and stirred for 6 hours under reflux. Then the reaction mixture was cooled to 0 ° C, 0.62 g of sodium borohydride was added. The mixture was stirred at room temperature for 6 hours. Then the reaction mixture was cooled to 0 ° C, 30 ml of water and 50 ml of ethyl acetate were added. While stirring the mixture, 90 ml of 1N was added dropwise. hydrochloric acid, then was extracted three times with 50 ml of ethyl acetate. The organic layer was washed with 50 ml of a saturated aqueous solution of sodium bicarbonate and 50 ml of a saturated aqueous solution of sodium chloride, dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.51 g of a trans form (hereinafter referred to as the present compound (51t)) and 0.59 g of a cis form (hereinafter referred to as the present compound (51c)) 2- (4-cyanocyclohexyl) - 2- (3,3,3-trifluoropropylsulfonyl) acetonitrile represented by the following formula (51).

The present compound (51c):

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.40-1.54 (2H, m), 1.64-1.79 (2H, m), 1.89-1 , 99 (1H, m), 2.21-2.30 (2H, m), 2.30-2.38 (1H, m), 2.41-2.54 (2H, m), 2.69 -2.84 (2H, m), 3.37-3.47 (1H, m), 3.51-3.59 (1H, m), 3.83 (1H, d).

The present compound (51t):

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.64-1.88 (4H, m), 1.95-2.02 (1H, m), 2.09-2 , 19 (2H, m), 2.19-2.29 (1H, m), 2.41-2.51 (1H, m), 2.51-2.69 (2H, m), 3.00 -3.05 (1H, m), 3.41-3.50 (1H, m), 3.54-3.63 (1H, m), 3.83 (1H, d).

Synthesis Example 51

To a solution of 0.34 g of the present compound (27) in 10 ml of acetonitrile, 0.21 g of 1,2-ethanedithiol and 0.05 g of tetrabutylammonium tribromide were added, and the mixture was stirred at room temperature for 1 hour. To the reaction mixture was added 100 ml of ethyl acetate and then 50 ml of a saturated aqueous solution of sodium bicarbonate. The solution was stirred for 1 hour and then was extracted twice with 50 ml of ethyl acetate. The organic layers were combined, washed with 50 ml of a saturated aqueous solution of sodium bicarbonate and 50 ml of a saturated aqueous solution of sodium chloride, dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.36 g of 2- (1,4-dithiaspiro [4.5] dec-8-yl) -2- (3,3,3-trifluoropropylsulfonyl) acetonitrile (hereinafter referred to as the present compound (52 )) represented by the formula:

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.67-1.83 (2H, m), 1.88-1.97 (1H, m), 1.98-2 09 (2H, m), 2.17-2.30 (3H, m), 2.36-2.48 (1H, m), 2.67-2.85 (2H, m), 3.24 -3.36 (4H, m), 3.48-3.50 (1H, m), 3.60-3.83 (1H, m), 3.86 (1H, d).

Synthesis Example 52

Stage 52-1

To a suspension of 22.85 g of potassium thioacetate in 200 ml of methanol was added dropwise 54.79 g of 1-iodo-3,3,4,4,4-pentafluorobutane at 0 ° C for 30 minutes in a nitrogen atmosphere and the mixture was stirred at room temperature temperature for 1 hour. During this time, the reaction mixture was analyzed by thin layer chromatography (TLC) to confirm the formation of 3,3,4,4,4-pentafluorobutylthioacetate. Then the mixture was cooled to 0 ° C, 40.52 g of a 28% solution of sodium methoxide in methanol was added dropwise over 15 minutes. The mixture was stirred at room temperature for 1 hour. 16.61 g of chloroacetonitrile was added to the mixture at 0 ° C, and the mixture was stirred at room temperature for 3 hours. The reaction vessel was cooled in an ice bath and an aqueous solution of 1N was added to the reaction mixture. hydrochloric acid. Methanol was distilled off under reduced pressure. The remainder of the reaction mixture was extracted twice with 200 ml of tert-butyl methyl ether. The organic layers were combined, washed with a saturated aqueous solution of sodium chloride, dried over sodium sulfate, filtered and then reduced pressure to distill off the solvent. The residue was subjected to silica gel column chromatography to obtain 17.81 g (3,3,4,4,4-pentafluorobutylthio) acetonitrile.

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 2.35-2.52 (2H, m), 2.94-3.03 (2H, m), 3.36 (2H , from).

Alternatively, 3,3,4,4,4-pentafluorobutylthioacetate was synthesized according to step 27-1 of synthesis example 27, except that instead of 1-iodine-3,3,3-trifluoropropane, 1.22 g of 1-iodine-3 was used , 3,4,4,4-pentafluorobutane.

Stage 52-2

To a suspension of 17.81 g (3,3,4,4,4-pentafluorobutylthio) acetonitrile and 0.28 g of sodium tungstate dinitrate in 30 ml of water was added 8.94 ml of 31% aqueous hydrogen peroxide with stirring the suspension. The temperature of the mixture was raised to 65 ° C, and 8.94 ml of 31% aqueous hydrogen peroxide was added. The mixture was stirred at 70 ° C for 1 hour. In the middle of the reaction, the formation of the expected sulfoxide compound was confirmed by thin layer chromatography (TLC). The reaction mixture was cooled to room temperature and 30 ml of an aqueous solution of sodium sulfite was added, then 150 ml of ethyl acetate were extracted three times. The organic layers were combined, washed with an aqueous saturated sodium chloride solution, dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue was crystallized from chloroform: hexane = 1: 2 to obtain 17.84 g (3,3,4,4,4-pentafluorobutylsulfonyl) acetonitrile represented by the formula:

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 2.66-2.80 (2H, m), 3.53-3.58 (2H, m), 4.09 (2H , from).

Stage 52-3

A mixture of 7.74 g of (3,3,4,4,4-pentafluorobutylsulfonyl) acetonitrile, 100 ml of toluene, 0.23 g of DL-proline and 4.81 g of 1,4-cyclohexanedione monoethylene ketal was heated and stirred for 3 hours at refluxing. Then 20 ml of toluene were distilled off, the reaction mixture was cooled to room temperature. 100 ml of tetrahydrofuran was added to the reaction mixture. Then it was cooled to 0 ° C, 1.17 g of sodium borohydride was added to the reaction mixture. The mixture was stirred at room temperature for 6 hours, then cooled to 0 ° C and 100 ml of water and 100 ml of ethyl acetate were added. 100 ml of 1N was added dropwise to the mixture. hydrochloric acid while stirring the mixture, then was extracted twice with 100 ml of ethyl acetate. The organic layer was washed with 100 ml of a saturated aqueous solution of sodium bicarbonate, 100 ml of a saturated aqueous solution of sodium chloride and then 100 ml of water, dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 5.00 g of 2- (1,4-dioxaspiro [4.5] dec-8-yl) -2- (3,3,4,4,4-pentafluorobutylsulfonyl) acetonitrile (hereinafter referred to as the present compound (53)) represented by the following formula (53).

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.58-1.91 (7H, m), 2.13-2.22 (1H, m), 2.39-2 , 51 (1H, m), 2.58-2.82 (2H, m), 3.40-3.50 (1H, m), 3.53-3.63 (1H, m), 3.87 (1H, d), 3.93-3.98 (4H, m).

Synthesis Example 53

A mixture of 5.00 g of the present compound (53), 14 ml of acetic acid and 6 ml of water was heated to 70 ° C and stirred for 10 hours. Then the reaction mixture was cooled to room temperature, 100 ml of ethyl acetate was added. The mixture was slowly added to 100 ml of a saturated aqueous sodium bicarbonate solution. The solution was stirred for 1 hour, then was extracted twice with 100 ml of ethyl acetate. The organic layers were combined, washed with 100 ml of a saturated aqueous solution of sodium bicarbonate and 100 ml of a saturated aqueous solution of sodium chloride, dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 3.56 g of 2- (4-oxocyclohexyl) -2- (3,3,4,4,4-pentafluorobutylsulfonyl) acetonitrile (hereinafter referred to as the present compound (54)) represented by the formula:

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.84-1.97 (2H, m), 2.17-2.26 (1H, m), 2.40-2 61 (5H, m), 2.81-2.85 (2H, m), 3.44-3.54 (1H, m), 3.59-3.70 (1H, m), 3.99 (1H, d).

Synthesis Example 54

To a solution of 0.35 g of the present compound (54) in 10 ml of tetrahydrofuran was added 0.75 g of pyridine and 0.79 g of methoxyamine hydrochloride, and the mixture was stirred at room temperature for 3 hours. To the reaction mixture was added 30 ml of 1 N. an aqueous solution of hydrochloric acid, then was extracted twice with 50 ml of ethyl acetate. The organic layers were combined and washed with 50 ml of a saturated aqueous solution of sodium bicarbonate and 50 ml of an aqueous saturated solution of sodium chloride. The resulting organic layer was dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.34 g of 2- [4- (methoxyimino) cyclohexyl] -2- (3,3,4,4,4-pentafluorobutylsulfonyl) acetonitrile (hereinafter referred to as the present compound (55)), represented by the formula:

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.55-1.72 (2H, m), 1.80-1.92 (1H, m), 1.95-2 11 (1H, m), 2.17-2.28 (1H, m), 2.31-2.45 (1H, m), 2.48-2.58 (1H, m), 2.61 -2.80 (3H, m), 3.33-3.40 (1H, m), 3.42-3.50 (1H, m), 3.55-3.65 (1H, m), 3 83 (3H, s); 3.89 (1H, d).

Synthesis Example 55

To a solution of 2.88 g of the present compound (15) in 10 ml of pyridine was added 1.91 g of p-toluenesulfonyl chloride and the mixture was stirred at room temperature for 3 hours. To the reaction solution was added 30 ml of 1 N. an aqueous solution of hydrochloric acid, then was extracted twice with 50 ml of ethyl acetate. The organic layers were combined, washed with 50 ml of a saturated aqueous solution of sodium bicarbonate and 50 ml of a saturated aqueous solution of sodium chloride. The resulting organic layer was dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue was dissolved in 20 ml of toluene. 1.50 g of sodium iodide and 1.52 g of 1,8-diazabicyclo [5.4.0] undec-7-ene were added to the solution, the mixture was heated to 110 ° C and stirred for 10 hours. To the reaction solution was added 30 ml of 1 N. an aqueous solution of hydrochloric acid, then was extracted twice with 50 ml of ethyl acetate. The organic layers were combined and washed successively with 50 ml of a saturated aqueous solution of sodium bicarbonate and 50 ml of a saturated aqueous solution of sodium chloride. The resulting organic layer was dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 1.01 g of 1-methylene-4- (3,3,3-trifluoropropylsulfonylmethyl) cyclohexanone (hereinafter referred to as the present compound (56)) represented by the formula:

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.20-1.31 (2H, m), 2.03-2.17 (4H, m), 2.22-2 36 (3H, m), 2.62-2.74 (2H, m), 2.95 (2H, d), 3.16-3.21 (2H, m), 4.66 (2H, s )

Synthesis Example 56

To a solution of 0.60 g of the present compound (56) in 4 ml of dichloromethane was added 0.86 g of bromoform, 0.44 g of sodium hydroxide and 0.02 g of benzyltriethylammonium chloride, and the mixture was stirred at 30 ° C. for 4 hours under ultrasonic irradiation. To the reaction mixture was added 20 ml of an aqueous solution of 2 N. hydrochloric acid, then was extracted twice with 30 ml of ethyl acetate. The organic layers were combined, washed successively with 30 ml of a saturated aqueous solution of sodium bicarbonate and 30 ml of a saturated aqueous solution of sodium chloride, dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.31 g of 1,1-dibromo-6- (3,3,3-trifluoropropylsulfonylmethyl) spiro [2,5] octane (hereinafter referred to as the present compound (57)) represented by the formula:

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.23-1.34 (2H, m), 1.39 (2H, s), 1.59-1.67 (2H m), 1.85-1.95 (2H, m), 2.07-2.15 (2H, m), 2.16-2.25 (1H, m), 2.63-2.75 (2H, m), 2.99 (2H, d), 3.17-3.21 (2H, m).

Synthesis Example 57

According to the procedure of Synthesis Example 56, except that 0.71 g of chloroform was used instead of bromoform, 0.41 g of 1,1-dichloro-6- (3,3,3-trifluoropropylsulfonylmethyl) spiro [2,5] octane ( hereinafter referred to as the present compound (58)) represented by the formula:

.

.

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.24-1.35 (2H, m), 1.53-1.62 (4H, m), 1.84-1 93 (2H, m), 2.08-2.15 (2H, m), 2.16-2.26 (1H, m), 2.63-2.75 (2H, m), 2.99 (2H, d), 3.18-3.22 (2H, m).

Synthesis Example 58

To a solution of 0.46 g of the present compound (54) in 10 ml of tetrahydrofuran was added 0.86 g of pyridine and 0.86 g of an aqueous solution of 30% ethoxyamine hydrochloride, and the mixture was stirred at room temperature for 3 hours. To the reaction mixture was added 30 ml of 1 N. hydrochloric acid solution, then was extracted twice with 50 ml of ethyl acetate. The organic layers were combined and washed with 50 ml of a saturated aqueous solution of sodium bicarbonate and 50 ml of a saturated aqueous solution of sodium chloride. The resulting organic layer was dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.34 g of 2- [4- (methoxyimino) cyclohexyl] -2- (3,3,4,4,4-pentafluorobutylsulfonyl) acetonitrile (hereinafter referred to as the present compound (59)), represented by the formula:

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.25 (3H, t), 1.55-1.73 (2H, m), 1.76-1.92 (1H , m), 1.94-2.09 (1H, m), 2.16-2.29 (1H, m), 2.31-2.44 (1H, m), 2.48-2.57 (1H, m), 2.62-2.79 (3H, m), 3.36-3.51 (2H, m), 3.54-3.65 (1H, m), 3.88 (1H d) 4.08 (2H, q).

Synthesis Example 59

Stage 59-1

According to the procedure of synthesis example 53, except that instead of 1-iodine-3,3,4,4,4-pentafluorobutane, 4.19 g of 1-iodo-3- (trifluoromethyl) -3,4,4,4- was used tetrafluorobutane, 4.77 g of (3- (trifluoromethyl) -3,4,4,4-tetrafluorobutylthio) acetonitrile were obtained.

Stage 59-2

To a suspension of 16.14 g of a double salt of 2KHSO ₅ · KHSO ₄ · K ₂ SO ₄ (Oxone, registered trademark) in 50 ml of water was added dropwise a solution of 4.77 g (3- (trifluoromethyl) -3,4,4, 4-tetrafluorobutylthio) acetonitrile in 50 ml of methanol at room temperature for 60 minutes under nitrogen atmosphere and the mixture was stirred for 2 hours. 50 ml of an aqueous solution of 10% sodium sulfite was added to the reaction mixture, then 100 ml of ethyl acetate was extracted twice. The organic layers were combined, washed with 50 ml of an aqueous solution of 10% sodium sulfite and 50 ml of a saturated aqueous solution of sodium chloride, dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 4.00 g of (3- (trifluoromethyl) -3,4,4,4-tetrafluorobutylsulfonyl) acetonitrile represented by the formula:

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 2.70-2.81 (2H, m), 3.50-3.55 (2H, m), 4.08 (2H , from).

Stage 59-3

A mixture of 4.00 g of (3- (trifluoromethyl) -3,4,4,4-tetrafluorobutylsulfonyl) acetonitrile, 50 ml of toluene, 0.15 g of DL-proline and 2.28 g of 1,4-cyclohexanedione monoethylene ketal was heated and stirred in for 3 hours at the boil under reflux. Then 30 ml of toluene was distilled off, the reaction mixture was cooled to 0 ° C. 0.25 g of sodium borohydride and 2 ml of N, N-dimethylformamide were added to the reaction mixture. The mixture was stirred at room temperature for 6 hours, then cooled to 0 ° C and 50 ml of water and 50 ml of ethyl acetate were added. To the mixture was added dropwise 20 ml of 1 N. hydrochloric acid while stirring the mixture, then was extracted twice with 100 ml of ethyl acetate. The organic layer was washed with 100 ml of a saturated aqueous solution of sodium bicarbonate and 100 ml of a saturated aqueous solution of sodium chloride, dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 4.41 g of 2- (1,4-dioxaspiro [4,5] dec-8-yl) -2- (3- (trifluoromethyl) -3,4,4,4- pentafluorobutylsulfonyl) acetonitrile (hereinafter referred to as the present compound (60)) represented by the following formula (60).

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.51-2.22 (8H, m), 2.40-2.51 (1H, m), 2.64-2 , 83 (2H, m), 3.37-3.48 (1H, m), 3.49-3.61 (1H, m), 3.86-3.89 (1H, m), 3.90 3.99 (4H, m).

Synthesis Example 60

A mixture of 4.41 g of the present compound (60), 14 ml of acetic acid, 6 ml of water, 1.50 g of methoxyamine hydrochloride and 1.47 g of sodium acetate were heated to 100 ° C and stirred for 10 hours. The reaction mixture was cooled to room temperature and 100 ml of ethyl acetate was added. The mixture was slowly added to 100 ml of a saturated aqueous sodium bicarbonate solution. The mixture was stirred for 1 hour, then was extracted twice with 100 ml of ethyl acetate. The organic layers were combined, washed with 100 ml of a saturated aqueous solution of sodium bicarbonate and 100 ml of a saturated aqueous solution of sodium chloride, dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 3.61 g of 2- (4-methoxyiminocyclohexyl) -2- (3- (trifluoromethyl) -3,4,4,4-tetrafluorobutylsulfonyl) acetonitrile (hereinafter referred to as the present compound (61)) represented by the following formula (61).

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.52-1.72 (2H, m), 1.81-1.91 (1H, m), 1.96-2 08 (1H, m), 2.16-2.28 (1H, m), 2.31-2.44 (1H, m), 2.50-2.57 (1H, m), 2.62 -2.82 (3H, m), 3.33-3.48 (2H, m), 3.53-3.63 (1H, m), 3.83 (3H, s), 3.89 (1H , e).

Synthesis Example 61

Stage 61-1

A mixture of 42.65 g of 3,3,4,4,5,5,6,6,6-nonafluorohexyl-p-toluenesulfonate, 100 ml of N, N-dimethylformamide and 11.65 g of potassium thioacetate was heated and stirred at 80 ° C for 4 hours in a nitrogen atmosphere. The reaction vessel was cooled in an ice bath. An aqueous solution of 1N was added to the reaction mixture. hydrochloric acid and the mixture was extracted twice with 200 ml of ethyl acetate. The organic layers were combined, washed with an aqueous saturated sodium chloride solution, dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 18.91 g of 3,3,4,4,5,5,6,6,6-nonafluorohexylthioacetate represented by the formula:

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 2.28-2.45 (5H, m), 3.04-3.13 (2H, m)

Stage 61-2

A solution of 18.91 g of 3.3,4,4,5,5,6,6,6-nonafluorohexylthioacetate in 60 ml of tetrahydrofuran was cooled to 0 ° C. 11.32 g of a 28% solution of sodium methoxide in methanol was added dropwise thereto over 15 minutes and then stirred at room temperature for 1 hour. 4.40 g of chloroacetonitrile was added to the mixture at 0 ° C, and then stirred at room temperature for 3 hours. The reaction vessel was cooled in an ice bath. An aqueous saturated sodium chloride solution was added to the reaction mixture, and the mixture was extracted twice with 100 ml of tert-butyl methyl ether. The organic layers were combined, washed with an aqueous saturated sodium chloride solution, dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 15.70 g (3,3,4,4,5,5,6,6,6-nonafluorohexylthio) acetonitrile.

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 2.40-2.59 (2H, m), 2.93-3.06 (2H, m), 3.38 (2H , from)

Stage 61-3

To a suspension of 15.10 g of a double salt of 2KHSO ₅ · KHSO ₄ · K ₂ SO ₄ (Oxone, registered trademark) in 100 ml of water was added dropwise a solution of 4.77 g (3,3,4,4,5,5, 6,6,6-nonafluorohexylthio) acetonitrile in 100 ml of methanol at -20 ° C for 60 minutes in a nitrogen atmosphere and the mixture was stirred for 2 hours. 50 ml of an aqueous 10% sodium sulfite solution was added to the reaction mixture, then 100 ml of ethyl acetate was extracted twice. The organic layers were combined, washed with 50 ml of an aqueous 10% sodium sulfite solution and 50 ml of a saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 12.56 g (3,3,4,4,5,5,6,6,6-nonafluorohexylsulfinyl) acetonitrile represented by the formula:

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 2.56-2.79 (2H, m), 3.10-3.29 (2H, m), 3.63-3 84 (2H, m).

Stage 61-4

To a suspension of 9.21 g of a double salt of 2KHSO ₅ · KHSO ₄ · K ₂ SO ₄ (Oxone, registered trademark) in 50 ml of water was added dropwise a solution of 6.80 g (3,3,4,4,5,5, 6,6,6-nonafluorohexylsulfinyl) acetonitrile in 50 ml of methanol at room temperature for 60 minutes under nitrogen atmosphere and the mixture was stirred overnight. 25 ml of an aqueous solution of 10% sodium sulfite was added to the reaction mixture, then 100 ml of ethyl acetate was extracted twice. The organic layers were combined, washed with 25 ml of an aqueous solution of 10% sodium sulfite and 50 ml of a saturated aqueous solution of sodium chloride, dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 5.4 g (3,3,4,4,5,5,6,6,6-nonafluorohexylsulfonyl) acetonitrile represented by the formula:

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 2.69-2.83 (2H, m), 3.54-3.60 (2H, m), 4.09 (2H , from).

Stage 61-5

A mixture of 5.40 g (3,3,4,4,5,5,6,6,6-nonafluorohexylsulfonyl) acetonitrile, 60 ml of toluene, 0.18 g of DL-proline and 2.77 g of 1,4-cyclohexanedione monoethylene ketal heated and stirred for 3 hours at the boil under reflux. Then 40 ml of toluene were distilled off, the reaction mixture was cooled to room temperature. The mixture was cooled to 0 ° C. and then 0.61 g of sodium borohydride was added. 3 ml of N, N-dimethylformamide was added to the reaction mixture. The mixture was stirred at room temperature for 6 hours and then cooled to 0 ° C. 50 ml of water and 50 ml of ethyl acetate were added. While stirring the mixture, 20 ml of 1N was added dropwise. aqueous hydrochloric acid, then was extracted twice with 100 ml of ethyl acetate. The organic layer was washed with 100 ml of a saturated aqueous solution of sodium bicarbonate, 100 ml of a saturated aqueous solution of sodium chloride and 100 ml of water, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was dissolved in 14 ml of acetic acid and 6 ml of water. The mixture was heated to 100 ° C and stirred for 8 hours. Then the reaction mixture was cooled to room temperature, 100 ml of ethyl acetate was added. The mixture was slowly added to 100 ml of a saturated aqueous sodium bicarbonate solution. The solution was stirred for 1 hour, then was extracted twice with 100 ml of ethyl acetate. The organic layers were combined, washed with 100 ml of a saturated aqueous solution of sodium bicarbonate and 100 ml of a saturated aqueous solution of sodium chloride, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 2.94 g of 2- (4-oxocyclohexyl) -2- (3,3,4,4,5,5,6,6,6-nonafluorohexylsulfonyl) acetonitrile (hereinafter referred to as the present compound) (62)) represented by the formula:

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.83-1.98 (2H, m), 2.17-2.26 (1H, m), 2.38-2 59 (5H, m), 2.67-2.97 (3H, m), 3.44-3.54 (1H, m), 3.60-3.70 (1H, m), 4.00 (1H, d).

Synthesis Example 62

To a solution of 2.69 g of the present compound (62) in 12 ml of tetrahydrofuran was added 0.52 g of pyridine and 0.55 g of methoxyamine hydrochloride, and the mixture was stirred at room temperature for 3 hours. To the reaction solution was added 30 ml of 1 N. an aqueous solution of hydrochloric acid, then was extracted twice with 50 ml of ethyl acetate. The organic layers were combined, washed with 50 ml of a saturated aqueous solution of sodium bicarbonate and 50 ml of a saturated aqueous solution of sodium chloride. The resulting organic layer was dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 2.86 g of 2- [4- (methoxyimino) cyclohexyl] -2- (3,3,4,4,5,5,6,6,6-nonafluorohexylsulfonyl) acetonitrile (hereinafter called the present compound (63)) represented by the formula:

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.49-1.73 (2H, m), 1.77-1.91 (1H, m), 1.95-2 09 (1H, m), 2.17-2.27 (1H, m), 2.31-2.43 (1H, m), 2.49-2.57 (1H, m), 2.62 -2.86 (3H, m), 3.32-3.39 (1H, m), 3.42-3.53 (1H, m), 3.55-3.66 (1H, m), 3 84 (3H, s), 3.90 (1H, d)

Synthesis Example 63

Stage 63-1

A mixture of 23.80 g of 1-iodine-4,4,4-trifluorobutane, 100 ml of N, N-dimethylformamide and 11.42 g of potassium thioacetate was heated and stirred at 80 ° C. for 4 hours under nitrogen. The reaction vessel was cooled in an ice bath. An aqueous solution of 1N was added to the reaction mixture. hydrochloric acid and the mixture was extracted twice with 100 ml of tert-butyl methyl ether. The organic layers were combined, washed with an aqueous saturated sodium chloride solution, dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 18.20 g of 4.4,4-trifluorobutylthioacetate represented by the formula:

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.82-1.92 (2H, m), 2.08-2.23 (2H, m), 2.35 (3H , s), 2.88-2.99 (2H, m)

Stage 63-2

A solution of 18.91 g of 4,4,4-trifluorobutylthioacetate in 60 ml of tetrahydrofuran was cooled to 0 ° C. 19.29 g of a 28% solution of sodium methoxide in methanol were added dropwise thereto over 15 minutes and then stirred at room temperature for 1 hour. 7.50 g of chloroacetonitrile was added to the mixture at 0 ° C and then stirred at room temperature for 3 hours. The reaction vessel was cooled in an ice bath. An aqueous saturated sodium chloride solution was added to the reaction mixture, and the mixture was extracted twice with 200 ml of tert-butyl methyl ether. The organic layers were combined, washed with an aqueous saturated sodium chloride solution, dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 17.82 g of (4,4,4-trifluorobutylthio) acetonitrile.

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.91-1.99 (2H, m), 2.17-2.32 (2H, m), 2.80-2 87 (2H, m).

Stage 63-3

To a suspension of 67.50 g of a double salt of 2KHSO ₅ · KHSO ₄ · K ₂ SO ₄ (Oxone, registered trademark) in 100 ml of water was added dropwise a solution of 17.82 g (4.4,4-trifluorobutylthio) acetonitrile in 100 ml methanol at room temperature for 60 minutes under nitrogen and the mixture was stirred overnight. To the reaction mixture was added 50 ml of an aqueous 10% sodium sulfite solution, then 200 ml of ethyl acetate was extracted twice. The organic layers were combined, washed with 50 ml of an aqueous 10% sodium sulfite solution and 50 ml of a saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 22.34 g (4,4,4-trifluorobutylsulfonyl) acetonitrile represented by the formula:

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 2.11-2.28 (2H, m), 2.32-2.46 (2H, m), 3.31-3 43 (2H, m); 4.03 (2H, s).

Stage 63-4

A mixture of 20.76 g of (4,4,4-trifluorobutylsulfonyl) acetonitrile, 200 ml of toluene, 1.11 g of DL-proline and 16.58 g of 1,4-cyclohexanedione monoethylene ketal was heated and stirred for 5 hours under reflux . Then, 100 ml of toluene was distilled off, the reaction mixture was cooled to 0 ° C. To the reaction mixture were added 1.89 g of sodium borohydride and 5 ml of N, N-dimethylformamide. The mixture was stirred at room temperature for 12 hours, then cooled to 0 ° C and 200 ml of water and 200 ml of ethyl acetate were added. 100 ml of 1N was added dropwise to the mixture. hydrochloric acid while stirring the mixture, then was extracted twice with 200 ml of ethyl acetate. The organic layer was washed with 100 ml of a saturated aqueous solution of sodium bicarbonate and 100 ml of a saturated aqueous solution of sodium chloride, dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 22.03 g of 2- (1,4-dioxaspiro [4,5] dec-8-yl) -2- (4,4,4-trifluorobutylsulfonyl) acetonitrile (hereinafter referred to as the present compound) (64)) represented by the following formula (64).

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.56-2.49 (13H, m), 3.27-3.43 (2H, m), 3.81 (1H d) 3.90-4.00 (4H, m).

Synthesis Example 64

A mixture of 22.03 g of the present compound (64), 70 ml of acetic acid and 30 ml of water was heated to 100 ° C and stirred for 8 hours. Then the reaction mixture was cooled to room temperature, 300 ml of ethyl acetate was added. The mixture was slowly added to 300 ml of a saturated aqueous sodium bicarbonate solution. The solution was stirred for 1 hour, then 200 ml of ethyl acetate were extracted twice. The organic layers were combined, washed with 300 ml of a saturated aqueous solution of sodium bicarbonate and 300 ml of a saturated aqueous solution of sodium chloride, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 15.82 g of 2- (4-oxocyclohexyl) -2- (4,4,4-trifluorobutylsulfonyl) acetonitrile (hereinafter referred to as the present compound (65)) represented by the formula:

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.81-1.99 (2H, m), 2.17-2.64 (10H, m), 2.82-2 95 (1H, m), 3.30-3.89 (2H, m), 3.93 (1H, d).

Synthesis Example 65

To a solution of 3.11 g of the present compound (65) in 10 ml of tetrahydrofuran was added 0.87 g of pyridine and 0.92 g of methoxyamine hydrochloride, and the mixture was stirred at room temperature for 3 hours. To the reaction solution was added 30 ml of 1 N. an aqueous solution of hydrochloric acid, then was extracted twice with 50 ml of ethyl acetate. The organic layers were combined, washed with 50 ml of a saturated aqueous solution of sodium bicarbonate and 50 ml of a saturated aqueous solution of sodium chloride. The resulting organic layer was dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 3.26 g of 2- [4- (methoxyimino) cyclohexyl] -2- (4,4,4-trifluorobutylsulfonyl) acetonitrile (hereinafter referred to as the present compound (66)) represented by the formula:

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.49-2.08 (4H, m), 2.14-2.44 (6H, m), 2.47-2 57 (1H, m), 2.59-2.70 (1H, m), 3.28-3.45 (3H, m), 3.80-3.85 (4H, m).

Synthesis Example 66

According to the procedure of Synthesis Example 65, except that 1.72 g of ethoxyamine hydrochloride was used instead of hydroxylamine hydrochloride, 2.87 g of 2- [4- (ethoxyimino) cyclohexyl] -2- (4,4,4-trifluorobutylsulfonyl) acetonitrile was obtained (hereinafter referred to as the present compound (67)) represented by the formula:

¹ H-NMR (CDCl ₃ , TMS, δ (ppm)): 1.25 (3H, t), 1.46-2.07 (4H, m), 2.14-2.43 (6H , m), 2.48-2.56 (1H, m), 2.59-2.70 (1H, m), 3.28-3.44 (3H, m), 3.83 (1H, d ), 4.05 (2H, q)

The following are specific examples of the compounds of the present invention.

The compound represented by formula (I-1):

where A, R ^a , R ^b , n and Q are any one of the combinations below.

The compound represented by formula (I-2):

where A, R ^a , R ^b , n and Q are any one of the combinations below.

The compound represented by formula (I-3):

where A, R ^a , R ^b , n and Q are any one of the combinations below.

The compound represented by formula (I-4):

where A, R ^a , R ^b , n and Q are any one of the combinations below.

The combinations A, R ^a , R ^b , n and Q for the compounds represented by formulas (I-1) to (I-4) are as follows.

[A; R ^a ; R ^b ; n; Q] =

[{3- (fluoromethyl) cyclopentyl}; H; H; 0; CF ₃ ];

[{3- (difluoromethyl) cyclopentyl}; H; H; 0; CF ₃ ];

[{3- (trifluoromethyl) cyclopentyl}; H; H; 0; CF ₃ ];

[{3-ethynylcyclopentyl}; H; H; 0; CF ₃ ];

[{3- (prop-1-ynyl) cyclopentyl}; H; H; 0; CF ₃ ];

[{3- (prop-2-ynyl) cyclopentyl}; H; H; 0; CF ₃ ];

[{3- (prop-2-ynyloxy) cyclopentyl}; H; H; 0; CF ₃ ];

[{3-ethynylcyclohexyl}; H; H; 0; CF ₃ ];

[{3- (prop-1-ynyl) cyclohexyl}; H; H; 0; CF ₃ ];

[{3- (prop-2-ynyl) cyclohexyl}; H; H; 0; CF ₃ ];

[{3- (prop-2-ynyloxy) cyclohexyl}; H; H; 0; CF ₃ ];

[{4-fluorocyclohexyl}; H; H; 0; CF ₃ ];

[{4,4-difluorocyclohexyl}; H; H; 0; CF ₃ ];

[{4-ethynylcyclohexyl}; H; H; 0; CF ₃ ];

[{4- (prop-1-ynyl) cyclohexyl}; H; H; 0; CF ₃ ];

[{4- (prop-2-ynyl) cyclohexyl}; H; H; 0; CF ₃ ];

[{4- (3-methoxyprop-1-ynyl) cyclohexyl}; H; H; 0; CF ₃ ];

[{4- (3-dimethylaminoprop-1-ynyl) cyclohexyl}; H; H; 0; CF ₃ ];

[{4- (4-methoxycarbonylbut-1-ynyl) cyclohexyl}; H; H; 0; CF ₃ ];

[{cyclopent-1-enyl}; H; H; 0; CF ₃ ];

[{3- (prop-1-ynyl) cyclopent-1-enyl}; H; H; 0; CF ₃ ];

[{3- (prop-2-ynyl) cyclopent-1-enyl}; H; H; 0; CF ₃ ];

[{cyclopent-2-enyl}; H; H; 0; CF ₃ ];

[{3- (prop-1-ynyl) cyclopent-2-enyl}; H; H; 0; CF ₃ ];

[{3- (prop-2-ynyl) cyclopent-2-enyl}; H; H; 0; CF ₃ ];

[{cyclopent-3-enyl}; H; H; 0; CF ₃ ];

[{3- (prop-1-ynyl) cyclopent-3-enyl}; H; H; 0; CF ₃ ];

[{3- (prop-2-ynyl) cyclopent-3-enyl}; H; H; 0; CF ₃ ];

[{3-ethynylcyclohex-1-enyl}; H; H; 0; CF ₃ ];

[{3- (prop-1-ynyl) cyclohex-1-enyl}; H; H; 0; CF ₃ ];

[{3- (prop-2-ynyl) cyclohex-1-enyl}; H; H; 0; CF ₃ ];

[{4-fluorocyclohex-1-enyl}; H; H; 0; CF ₃ ];

[{4- (prop-2-enyl) cyclohex-1-enyl}; H; H; 0; CF ₃ ];

[{4-ethynylcyclohex-1-enyl}; H; H; 0; CF ₃ ];

[{4- (prop-1-ynyl) cyclohex-1-enyl}; H; H; 0; CF ₃ ];

[{4- (prop-2-ynyl) cyclohex-1-enyl}; H; H; 0; CF ₃ ];

[{3- (prop-1-ynyl) cyclohex-2-enyl}; H; H; 0; CF ₃ ];

[{3- (prop-2-ynyl) cyclohex-2-enyl}; H; H; 0; CF ₃ ];

[{4- (prop-2-enyl) cyclohex-2-enyl}; H; H; 0; CF ₃ ];

[{4-ethynylcyclohex-2-enyl}; H; H; 0; CF ₃ ];

[{4- (prop-1-ynyl) cyclohex-2-enyl}; H; H; 0; CF ₃ ];

[{4- (prop-2-ynyl) cyclohex-2-enyl}; H; H; 0; CF ₃ ];

[{3- (prop-1-ynyl) cyclohex-3-enyl}; H; H; 0; CF ₃ ];

[{3- (prop-2-ynyl) cyclohex-3-enyl}; H; H; 0; CF ₃ ];

[{4-fluorocyclohex-3-enyl}; H; H; 0; CF ₃ ];

[{4- (prop-2-enyl) cyclohex-3-enyl}; H; H; 0; CF ₃ ];

[{4-ethynylcyclohex-3-enyl}; H; H; 0; CF ₃ ];

[{4- (prop-1-ynyl) cyclohex-3-enyl}; H; H; 0; CF ₃ ];

[{4- (prop-2-ynyl) cyclohex-3-enyl}; H; H; 0; CF ₃ ];

[{2,2-dichlorocyclopropyl}; H; H; 2; CF ₃ ];

[{2,2-difluorocyclopropyl}; H; H; 2; CF ₃ ];

[{2,2-dimethylcyclopropyl}; H; H; 2; CF ₃ ];

[{3-cyanocyclopentyl}; H; H; 2; CF ₃ ];

[{3,3-fluorocyclopentyl}; H; H; 2; CF ₃ ];

[{3,3-difluorocyclopentyl}; H; H; 2; CF ₃ ];

[{3- (fluoromethyl) cyclopentyl}; H; H; 2; CF ₃ ];

[{3- (difluoromethyl) cyclopentyl}; H; H; 2; CF ₃ ];

[{3- (trifluoromethyl) cyclopentyl}; H; H; 2; CF ₃ ];

[{3-vinylcyclopentyl}; H; H; 2; CF ₃ ];

[{3- (2,2-difluorovinyl) cyclopentyl}; H; H; 2; CF ₃ ];

[{3-ethynylcyclopentyl}; H; H; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclopentyl}; H; H; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclopentyl}; H; H; 2; CF ₃ ];

[{3- (1-fluoroprop-2-ynyl) cyclopentyl}; H; H; 2; CF ₃ ];

[{3- (but-1-ynyl) cyclopentyl}; H; H; 2; CF ₃ ];

[{3- (but-2-ynyl) cyclopentyl}; H; H; 2; CF ₃ ];

[{3- (but-3-ynyl) cyclopentyl}; H; H; 2; CF ₃ ];

[{3- (prop-2-ynyloxy) cyclopentyl}; H; H; 2; CF ₃ ];

[{3,3-difluorocyclohexyl}; H; H; 2; CF ₃ ];

[{3-ethynylcyclohexyl}; H; H; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclohexyl}; H; H; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclohexyl}; H; H; 2; CF ₃ ];

[{3- (but-2-ynyl) cyclohexyl}; H; H; 2; CF ₃ ];

[{3- (but-3-ynyl) cyclohexyl}; H; H; 2; CF ₃ ];

[{3- (prop-2-ynyloxy) cyclohexyl}; H; H; 2; CF ₃ ];

[{4,4-difluorocyclohexyl}; H; H; 2; CF ₃ ];

[{4-vinylcyclohexyl}; H; H; 2; CF ₃ ];

[{4- (2,2-difluorovinyl) cyclohexyl}; H; H; 2; CF ₃ ];

[{4- (prop-2-enyl) cyclohexyl}; H; H; 2; CF ₃ ];

[{4-ethynylcyclohexyl}; H; H; 2; CF ₃ ];

[{4- (2-bromoethynyl) cyclohexyl}; H; H; 2; CF ₃ ];

[{4- (2-iodoethinyl) cyclohexyl}; H; H; 2; CF ₃ ];

[{4-ethynyl-4-fluorocyclohexyl}; H; H; 2; CF ₃ ];

[{4- (prop-1-ynyl) cyclohexyl}; H; H; 2; CF ₃ ];

[{4- (prop-2-ynyl) cyclohexyl}; H; H; 2; CF ₃ ];

[{4- (but-2-ynyl) cyclohexyl}; H; H; 2; CF ₃ ];

[{4- (but-3-ynyl) cyclohexyl}; H; H; 2; CF ₃ ];

[{4- (pent-1-ynyl) cyclohexyl}; H; H; 2; CF ₃ ];

[{4- (pent-2-ynyl) cyclohexyl}; H; H; 2; CF ₃ ];

[{4- (pent-3-ynyl) cyclohexyl}; H; H; 2; CF ₃ ];

[{4- (3-methoxyprop-1-ynyl) cyclohexyl}; H; H; 2; CF ₃ ];

[{4- (4-methoxybut-1-ynyl) cyclohexyl}; H; H; 2; CF ₃ ];

[{4- (4-methoxybut-2-ynyl) cyclohexyl}; H; H; 2; CF ₃ ];

[{4- (5-methoxypent-1-ynyl) cyclohexyl}; H; H; 2; CF ₃ ];

[{4- (5-methoxypent-2-ynyl) cyclohexyl}; H; H; 2; CF ₃ ];

[{4- (3-dimethylaminoprop-1-ynyl) cyclohexyl}; H; H; 2; CF ₃ ];

[{4- (4-dimethylaminobut-1-ynyl) cyclohexyl}; H; H; 2; CF ₃ ];

[{4- (4-dimethylaminobut-2-ynyl) cyclohexyl}; H; H; 2; CF ₃ ];

[{4- (5-dimethylaminopent-1-ynyl) cyclohexyl}; H; H; 2; CF ₃ ];

[{4- (5-dimethylaminopent-2-ynyl) cyclohexyl}; H; H; 2; CF ₃ ];

[{4- (2-methoxycarbonylethynyl) cyclohexyl}; H; H; 2; CF ₃ ];

[{4- (3-methoxycarbonylprop-1-ynyl) cyclohexyl}; H; H; 2; CF ₃ ];

[{4- (4-methoxycarbonylbut-1-ynyl) cyclohexyl}; H; H; 2; CF ₃ ];

[{4- (4-methoxycarbonylbut-2-ynyl) cyclohexyl}; H; H; 2; CF ₃ ];

[{4- (5-methoxycarbonylpent-1-ynyl) cyclohexyl}; H; H; 2; CF ₃ ];

[{4- (5-methoxycarbonylpent-2-ynyl) cyclohexyl}; H; H; 2; CF ₃ ];

[{4- (1-fluoroprop-2-ynyl) cyclohexyl}; H; H; 2; CF ₃ ];

[{4- (1,1-difluoroprop-2-ynyl) cyclohexyl}; H; H; 2; CF ₃ ];

[{4- (3-fluoroprop-1-ynyl) cyclohexyl}; H; H; 2; CF ₃ ];

[{4- (3,3-difluoroprop-1-ynyl) cyclohexyl}; H; H; 2; CF ₃ ];

[{4- (3,3,3-trifluoroprop-1-ynyl) cyclohexyl}; H; H; 2; CF ₃ ];

[{4- (4-fluorobut-1-ynyl) cyclohexyl}; H; H; 2; CF ₃ ];

[{4- (4-fluorobut-2-ynyl) cyclohexyl}; H; H; 2; CF ₃ ];

[{4- (5-fluoropent-1-ynyl) cyclohexyl}; H; H; 2; CF ₃ ];

[{4- (5-fluoropent-2-ynyl) cyclohexyl}; H; H; 2; CF ₃ ];

[{cyclopent-1-enyl}; H; H; 2; CF ₃ ];

[{3-cyanocyclopent-1-enyl}; H; H; 2; CF ₃ ];

[{3,3-difluorocyclopent-1-enyl}; H; H; 2; CF ₃ ];

[{3- (fluoromethyl) cyclopent-1-enyl}; H; H; 2; CF ₃ ];

[{3- (difluoromethyl) cyclopent-1-enyl}; H; H; 2; CF ₃ ];

[{3- (trifluoromethyl) cyclopent-1-enyl}; H; H; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclopent-1-enyl}; H; H; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclopent-1-enyl}; H; H; 2; CF ₃ ];

[{3- (1-fluoroprop-2-ynyl) cyclopent-1-enyl}; H; H; 2; CF ₃ ];

[{3- (but-2-ynyl) cyclopent-1-enyl}; H; H; 2; CF ₃ ];

[{3- (but-3-ynyl) cyclopent-1-enyl}; H; H; 2; CF ₃ ];

[{cyclopent-2-enyl}; H; H; 2; CF ₃ ];

[{3-cyanocyclopent-2-enyl}; H; H; 2; CF ₃ ];

[{3-fluorocyclopent-2-enyl}; H; H; 2; CF ₃ ];

[{3- (fluoromethyl) cyclopent-2-enyl}; H; H; 2; CF ₃ ];

[{3- (difluoromethyl) cyclopent-2-enyl}; H; H; 2; CF ₃ ];

[{3- (trifluoromethyl) cyclopent-2-enyl}; H; H; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclopent-2-enyl}; H; H; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclopent-2-enyl}; H; H; 2; CF ₃ ];

[{3- (1-fluoroprop-2-ynyl) cyclopent-2-enyl}; H; H; 2; CF ₃ ];

[{3- (but-2-ynyl) cyclopent-2-enyl}; H; H; 2; CF ₃ ];

[{3- (but-3-ynyl) cyclopent-2-enyl}; H; H; 2; CF ₃ ];

[{cyclopent-3-enyl}; H; H; 2; CF ₃ ];

[{3-cyanocyclopent-3-enyl}; H; H; 2; CF ₃ ];

[{3-fluorocyclopent-3-enyl}; H; H; 2; CF ₃ ];

[{3- (fluoromethyl) cyclopent-3-enyl}; H; H; 2; CF ₃ ];

[{3- (difluoromethyl) cyclopent-3-enyl}; H; H; 2; CF ₃ ];

[{3- (trifluoromethyl) cyclopent-3-enyl}; H; H; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclopent-3-enyl}; H; H; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclopent-3-enyl}; H; H; 2; CF ₃ ];

[{3- (1-fluoroprop-2-ynyl) cyclopent-3-enyl}; H; H; 2; CF ₃ ];

[{3- (but-2-ynyl) cyclopent-3-enyl}; H; H; 2; CF ₃ ];

[{3- (but-3-ynyl) cyclopent-3-enyl}; H; H; 2; CF ₃ ];

[{3-ethynylcyclohex-1-enyl}; H; H; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclohex-1-enyl}; H; H; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclohex-1-enyl}; H; H; 2; CF ₃ ];

[{3- (prop-2-ynyloxy) cyclohex-1-enyl}; H; H; 2; CF ₃ ];

[{4-fluorocyclohex-1-enyl}; H; H; 2; CF ₃ ];

[{4- (prop-2-enyl) cyclohex-1-enyl}; H; H; 2; CF ₃ ];

[{4-ethynylcyclohex-1-enyl}; H; H; 2; CF ₃ ];

[{4- (prop-1-ynyl) cyclohex-1-enyl}; H; H; 2; CF ₃ ];

[{4- (prop-2-ynyl) cyclohex-1-enyl}; H; H; 2; CF ₃ ];

[{3-ethynylcyclohex-2-enyl}; H; H; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclohex-2-enyl}; H; H; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclohex-2-enyl}; H; H; 2; CF ₃ ];

[{3- (prop-2-ynyloxy) cyclohex-2-enyl}; H; H; 2; CF ₃ ];

[{4-fluorocyclohex-2-enyl}; H; H; 2; CF ₃ ];

[{4- (prop-2-enyl) cyclohex-2-enyl}; H; H; 2; CF ₃ ];

[{4-ethynylcyclohex-2-enyl}; H; H; 2; CF ₃ ];

[{4- (prop-1-ynyl) cyclohex-2-enyl}; H; H; 2; CF ₃ ];

[{4- (prop-2-ynyl) cyclohex-2-enyl}; H; H; 2; CF ₃ ];

[{3-ethynylcyclohex-3-enyl}; H; H; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclohex-3-enyl}; H; H; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclohex-3-enyl}; H; H; 2; CF ₃ ];

[{3- (prop-2-ynyloxy) cyclohex-3-enyl}; H; H; 2; CF ₃ ];

[{4-fluorocyclohex-3-enyl}; H; H; 2; CF ₃ ];

[{4- (prop-2-enyl) cyclohex-3-enyl}; H; H; 2; CF ₃ ];

[{4-ethynylcyclohex-3-enyl}; H; H; 2; CF ₃ ];

[{4- (prop-1-ynyl) cyclohex-3-enyl}; H; H; 2; CF ₃ ];

[{4- (prop-2-ynyl) cyclohex-3-enyl}; H; H; 2; CF ₃ ];

[{3- (fluoromethyl) cyclopentyl}; H; H; 0; C ₂ F ₅ ];

[{3- (difluoromethyl) cyclopentyl}; H; H; 0; C ₂ F ₅ ];

[{3- (trifluoromethyl) cyclopentyl}; H; H; 0; C ₂ F ₅ ];

[{3-ethynylcyclopentyl}; H; H; 0; C ₂ F ₅ ];

[{3- (prop-1-ynyl) cyclopentyl}; H; H; 0; C ₂ F ₅ ];

[{3- (prop-2-ynyl) cyclopentyl}; H; H; 0; C ₂ F ₅ ];

[{3- (prop-2-ynyloxy) cyclopentyl}; H; H; 0; C ₂ F ₅ ];

[{3-ethynylcyclohexyl}; H; H; 0; C ₂ F ₅ ];

[{3- (prop-1-ynyl) cyclohexyl}; H; H; 0; C ₂ F ₅ ];

[{3- (prop-2-ynyl) cyclohexyl}; H; H; 0; C ₂ F ₅ ];

[{3- (prop-2-ynyloxy) cyclohexyl}; H; H; 0; C ₂ F ₅ ];

[{4-fluorocyclohexyl}; H; H; 0; C ₂ F ₅ ];

[{4,4-difluorocyclohexyl}; H; H; 0; C ₂ F ₅ ];

[{4-ethynylcyclohexyl}; H; H; 0; C ₂ F ₅ ];

[{4- (prop-1-ynyl) cyclohexyl}; H; H; 0; C ₂ F ₅ ];

[{4- (prop-2-ynyl) cyclohexyl}; H; H; 0; C ₂ F ₅ ];

[{4- (3-methoxyprop-1-ynyl) cyclohexyl}; H; H; 0; C ₂ F ₅ ];

[{4- (3-dimethylaminoprop-1-ynyl) cyclohexyl}; H; H; 0; C ₂ F ₅ ];

[{4- (4-methoxycarbonylbut-1-ynyl) cyclohexyl}; H; H; 0; C ₂ F ₅ ];

[{cyclopent-1-enyl}; H; H; 0; C ₂ F ₅ ];

[{3- (prop-1-ynyl) cyclopent-1-enyl}; H; H; 0; C ₂ F ₅ ];

[{3- (prop-2-ynyl) cyclopent-1-enyl}; H; H; 0; C ₂ F ₅ ];

[{cyclopent-2-enyl}; H; H; 0; C ₂ F ₅ ];

[{3- (prop-1-ynyl) cyclopent-2-enyl}; H; H; 0; C ₂ F ₅ ];

[{3- (prop-2-ynyl) cyclopent-2-enyl}; H; H; 0; C ₂ F ₅ ];

[{cyclopent-3-enyl}; H; H; 0; C ₂ F ₅ ];

[{3- (prop-1-ynyl) cyclopent-3-enyl}; H; H; 0; C ₂ F ₅ ];

[{3- (prop-2-ynyl) cyclopent-3-enyl}; H; H; 0; C ₂ F ₅ ];

[{3-ethynylcyclohex-1-enyl}; H; H; 0; C ₂ F ₅ ];

[{3- (prop-1-ynyl) cyclohex-1-enyl}; H; H; 0; C ₂ F ₅ ];

[{3- (prop-2-ynyl) cyclohex-1-enyl}; H; H; 0; C ₂ F ₅ ];

[{4-fluorocyclohex-1-enyl}; H; H; 0; C ₂ F ₅ ];

[{4- (prop-2-enyl) cyclohex-1-enyl}; H; H; 0; C ₂ F ₅ ];

[{4-ethynylcyclohex-1-enyl}; H; H; 0; C ₂ F ₅ ];

[{4- (prop-1-ynyl) cyclohex-1-enyl}; H; H; 0; C ₂ F ₅ ];

[{4- (prop-2-ynyl) cyclohex-1-enyl}; H; H; 0; C ₂ F ₅ ];

[{3- (prop-1-ynyl) cyclohex-2-enyl}; H; H; 0; C ₂ F ₅ ];

[{3- (prop-2-ynyl) cyclohex-2-enyl}; H; H; 0; C ₂ F ₅ ];

[{4- (prop-2-enyl) cyclohex-2-enyl}; H; H; 0; C ₂ F ₅ ];

[{4-ethynylcyclohex-2-enyl}; H; H; 0; C ₂ F ₅ ];

[{4- (prop-1-ynyl) cyclohex-2-enyl}; H; H; 0; C ₂ F ₅ ];

[{4- (prop-2-ynyl) cyclohex-2-enyl}; H; H; 0; C ₂ F ₅ ];

[{3- (prop-1-ynyl) cyclohex-3-enyl}; H; H; 0; C ₂ F ₅ ];

[{3- (prop-2-ynyl) cyclohex-3-enyl}; H; H; 0; C ₂ F ₅ ];

[{4-fluorocyclohex-3-enyl}; H; H; 0; C ₂ F ₅ ];

[{4- (prop-2-enyl) cyclohex-3-enyl}; H; H; 0; C ₂ F ₅ ];

[{4-ethynylcyclohex-3-enyl}; H; H; 0; C ₂ F ₅ ];

[{4- (prop-1-ynyl) cyclohex-3-enyl}; H; H; 0; C ₂ F ₅ ];

[{4- (prop-2-ynyl) cyclohex-3-enyl}; H; H; 0; C ₂ F ₅ ];

[{3- (fluoromethyl) cyclopentyl}; H; H; 2; C ₂ F ₅ ];

[{3- (difluoromethyl) cyclopentyl}; H; H; 2; C ₂ F ₅ ];

[{3- (trifluoromethyl) cyclopentyl}; H; H; 2; C ₂ F ₅ ];

[{3-ethynylcyclopentyl}; H; H; 2; C ₂ F ₅ ];

[{3- (prop-1-ynyl) cyclopentyl}; H; H; 2; C ₂ F ₅ ];

[{3- (prop-2-ynyl) cyclopentyl}; H; H; 2; C ₂ F ₅ ];

[{3- (prop-2-ynyloxy) cyclopentyl}; H; H; 2; C ₂ F ₅ ];

[{3-ethynylcyclohexyl}; H; H; 2; C ₂ F ₅ ];

[{3- (prop-1-ynyl) cyclohexyl}; H; H; 2; C ₂ F ₅ ];

[{3- (prop-2-ynyl) cyclohexyl}; H; H; 2; C ₂ F ₅ ];

[{3- (prop-2-ynyloxy) cyclohexyl}; H; H; 2; C ₂ F ₅ ];

[{4-fluorocyclohexyl}; H; H; 2; C ₂ F ₅ ];

[{4,4-difluorocyclohexyl}; H; H; 2; C ₂ F ₅ ];

[{4-ethynylcyclohexyl}; H; H; 2; C ₂ F ₅ ];

[{4- (prop-1-ynyl) cyclohexyl}; H; H; 2; C ₂ F ₅ ];

[{4- (prop-2-ynyl) cyclohexyl}; H; H; 2; C ₂ F ₅ ];

[{4- (3-methoxyprop-1-ynyl) cyclohexyl}; H; H; 2; C ₂ F ₅ ];

[{4- (3-dimethylaminoprop-1-ynyl) cyclohexyl}; H; H; 2; C ₂ F ₅ ];

[{4- (4-methoxycarbonylbut-1-ynyl) cyclohexyl}; H; H; 2; C ₂ F ₅ ];

[{cyclopent-1-enyl}; H; H; 2; C ₂ F ₅ ];

[{3- (prop-1-ynyl) cyclopent-1-enyl}; H; H; 2; C ₂ F ₅ ];

[{3- (prop-2-ynyl) cyclopent-1-enyl}; H; H; 2; C ₂ F ₅ ];

[{cyclopent-2-enyl}; H; H; 2; C ₂ F ₅ ];

[{3- (prop-1-ynyl) cyclopent-2-enyl}; H; H; 2; C ₂ F ₅ ];

[{3- (prop-2-ynyl) cyclopent-2-enyl}; H; H; 2; C ₂ F ₅ ];

[{cyclopent-3-enyl}; H; H; 2; C ₂ F ₅ ];

[{3- (prop-1-ynyl) cyclopent-3-enyl}; H; H; 2; C ₂ F ₅ ];

[{3- (prop-2-ynyl) cyclopent-3-enyl}; H; H; 2; C ₂ F ₅ ];

[{3-ethynylcyclohex-1-enyl}; H; H; 2; C ₂ F ₅ ];

[{3- (prop-1-ynyl) cyclohex-1-enyl}; H; H; 2; C ₂ F ₅ ];

[{3- (prop-2-ynyl) cyclohex-1-enyl}; H; H; 2; C ₂ F ₅ ];

[{4-fluorocyclohex-1-enyl}; H; H; 2; C ₂ F ₅ ];

[{4- (prop-2-enyl) cyclohex-1-enyl}; H; H; 2; C ₂ F ₅ ];

[{4-ethynylcyclohex-1-enyl}; H; H; 2; C ₂ F ₅ ];

[{4- (prop-1-ynyl) cyclohex-1-enyl}; H; H; 2; C ₂ F ₅ ];

[{4- (prop-2-ynyl) cyclohex-1-enyl}; H; H; 2; C ₂ F ₅ ];

[{3- (prop-1-ynyl) cyclohex-2-enyl}; H; H; 2; C ₂ F ₅ ];

[{3- (prop-2-ynyl) cyclohex-2-enyl}; H; H; 2; C ₂ F ₅ ];

[{4- (prop-2-enyl) cyclohex-2-enyl}; H; H; 2; C ₂ F ₅ ];

[{4-ethynylcyclohex-2-enyl}; H; H; 2; C ₂ F ₅ ];

[{4- (prop-1-ynyl) cyclohex-2-enyl}; H; H; 2; C ₂ F ₅ ];

[{4- (prop-2-ynyl) cyclohex-2-enyl}; H; H; 2; C ₂ F ₅ ];

[{3- (prop-1-ynyl) cyclohex-3-enyl}; H; H; 2; C ₂ F ₅ ];

[{3- (prop-2-ynyl) cyclohex-3-enyl}; H; H; 2; C ₂ F ₅ ];

[{4-fluorocyclohex-3-enyl}; H; H; 2; C ₂ F ₅ ];

[{4- (prop-2-enyl) cyclohex-3-enyl}; H; H; 2; C ₂ F ₅ ];

[{4-ethynylcyclohex-3-enyl}; H; H; 2; C ₂ F ₅ ];

[{4- (prop-1-ynyl) cyclohex-3-enyl}; H; H; 2; C ₂ F ₅ ];

[{4- (prop-2-ynyl) cyclohex-3-enyl}; H; H; 2; C ₂ F ₅ ];

[{3- (fluoromethyl) cyclopentyl}; H; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (difluoromethyl) cyclopentyl}; H; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (trifluoromethyl) cyclopentyl}; H; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3-ethynylcyclopentyl}; H; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclopentyl}; H; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclopentyl}; H; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-2-ynyloxy) cyclopentyl}; H; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3-ethynylcyclohexyl}; H; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclohexyl}; H; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclohexyl}; H; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-2-ynyloxy) cyclohexyl}; H; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4-fluorocyclohexyl}; H; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4,4-difluorocyclohexyl}; H; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4-ethynylcyclohexyl}; H; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (prop-1-ynyl) cyclohexyl}; H; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (prop-2-ynyl) cyclohexyl}; H; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (3-methoxyprop-1-ynyl) cyclohexyl}; H; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (3-dimethylaminoprop-1-ynyl) cyclohexyl}; H; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (4-methoxycarbonylbut-1-ynyl) cyclohexyl}; H; CO ₂ CH ₃ ; 2; CF ₃ ];

[{cyclopent-1-enyl}; H; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclopent-1-enyl}; H; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclopent-1-enyl}; H; CO ₂ CH ₃ ; 2; CF ₃ ];

[{cyclopent-2-enyl}; H; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclopent-2-enyl}; H; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclopent-2-enyl}; H; CO ₂ CH ₃ ; 2; CF ₃ ];

[{cyclopent-3-enyl}; H; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclopent-3-enyl}; H; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclopent-3-enyl}; H; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3-ethynylcyclohex-1-enyl}; H; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclohex-1-enyl}; H; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclohex-1-enyl}; H; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4-fluorocyclohex-1-enyl}; H; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (prop-2-enyl) cyclohex-1-enyl}; H; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4-ethynylcyclohex-1-enyl}; H; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (prop-1-ynyl) cyclohex-1-enyl}; H; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (prop-2-ynyl) cyclohex-1-enyl}; H; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclohex-2-enyl}; H; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclohex-2-enyl}; H; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (prop-2-enyl) cyclohex-2-enyl}; H; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4-ethynylcyclohex-2-enyl}; H; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (prop-1-ynyl) cyclohex-2-enyl}; H; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (prop-2-ynyl) cyclohex-2-enyl}; H; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclohex-3-enyl}; H; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclohex-3-enyl}; H; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4-fluorocyclohex-3-enyl}; H; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (prop-2-enyl) cyclohex-3-enyl}; H; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4-ethynylcyclohex-3-enyl}; H; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (prop-1-ynyl) cyclohex-3-enyl}; H; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (prop-2-ynyl) cyclohex-3-enyl}; H; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (fluoromethyl) cyclopentyl}; F; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (difluoromethyl) cyclopentyl}; F; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (trifluoromethyl) cyclopentyl}; F; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3-ethynylcyclopentyl}; F; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclopentyl}; F; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclopentyl}; F; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-2-ynyloxy) cyclopentyl}; F; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3-ethynylcyclohexyl}; F; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclohexyl}; F; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclohexyl}; F; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-2-ynyloxy) cyclohexyl}; F; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4-fluorocyclohexyl}; F; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4,4-difluorocyclohexyl}; F; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4-ethynylcyclohexyl}; F; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (prop-1-ynyl) cyclohexyl}; F; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (prop-2-ynyl) cyclohexyl}; F; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (3-methoxyprop-1-ynyl) cyclohexyl}; F; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (3-dimethylaminoprop-1-ynyl) cyclohexyl}; F; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (4-methoxycarbonylbut-1-ynyl) cyclohexyl}; F; CO ₂ CH ₃ ; 2; CF ₃ ];

[{cyclopent-1-enyl}; F; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclopent-1-enyl}; F; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclopent-1-enyl}; F; CO ₂ CH ₃ ; 2; CF ₃ ];

[{cyclopent-2-enyl}; F; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclopent-2-enyl}; F; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclopent-2-enyl}; F; CO ₂ CH ₃ ; 2; CF ₃ ];

[{cyclopent-3-enyl}; F; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclopent-3-enyl}; F; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclopent-3-enyl}; F; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3-ethynylcyclohex-1-enyl}; F; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclohex-1-enyl}; F; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclohex-1-enyl}; F; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4-fluorocyclohex-1-enyl}; F; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (prop-2-enyl) cyclohex-1-enyl}; F; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4-ethynylcyclohex-1-enyl}; F; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (prop-1-ynyl) cyclohex-1-enyl}; F; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (prop-2-ynyl) cyclohex-1-enyl}; F; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclohex-2-enyl}; F; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclohex-2-enyl}; F; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (prop-2-enyl) cyclohex-2-enyl}; F; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4-ethynylcyclohex-2-enyl}; F; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (prop-1-ynyl) cyclohex-2-enyl}; F; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (prop-2-ynyl) cyclohex-2-enyl}; F; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclohex-3-enyl}; F; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclohex-3-enyl}; F; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4-fluorocyclohex-3-enyl}; F; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (prop-2-enyl) cyclohex-3-enyl}; F; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4-ethynylcyclohex-3-enyl}; F; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (prop-1-ynyl) cyclohex-3-enyl}; F; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (prop-2-ynyl) cyclohex-3-enyl}; F; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (fluoromethyl) cyclopentyl}; Cl; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (difluoromethyl) cyclopentyl}; Cl; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (trifluoromethyl) cyclopentyl}; Cl; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3-ethynylcyclopentyl}; Cl; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclopentyl}; Cl; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclopentyl}; Cl; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-2-ynyloxy) cyclopentyl}; Cl; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3-ethynylcyclohexyl}; Cl; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclohexyl}; Cl; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclohexyl}; Cl; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-2-ynyloxy) cyclohexyl}; Cl; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4-fluorocyclohexyl}; Cl; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4,4-difluorocyclohexyl}; Cl; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4-ethynylcyclohexyl}; Cl; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (prop-1-ynyl) cyclohexyl}; Cl; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (prop-2-ynyl) cyclohexyl}; Cl; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (3-methoxyprop-1-ynyl) cyclohexyl}; Cl; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (3-dimethylaminoprop-1-ynyl) cyclohexyl}; Cl; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (4-methoxycarbonylbut-1-ynyl) cyclohexyl}; Cl; CO ₂ CH ₃ ; 2; CF ₃ ];

[{cyclopent-1-enyl}; Cl; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclopent-1-enyl}; Cl; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclopent-1-enyl}; Cl; CO ₂ CH ₃ ; 2; CF ₃ ];

[{cyclopent-2-enyl}; Cl; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclopent-2-enyl}; Cl; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclopent-2-enyl}; Cl; CO ₂ CH ₃ ; 2; CF ₃ ];

[{cyclopent-3-enyl}; Cl; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclopent-3-enyl}; Cl; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclopent-3-enyl}; Cl; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3-ethynylcyclohex-1-enyl}; Cl; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclohex-1-enyl}; Cl; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclohex-1-enyl}; Cl; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4-fluorocyclohex-1-enyl}; Cl; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (prop-2-enyl) cyclohex-1-enyl}; Cl; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4-ethynylcyclohex-1-enyl}; Cl; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (prop-1-ynyl) cyclohex-1-enyl}; Cl; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (prop-2-ynyl) cyclohex-1-enyl}; Cl; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclohex-2-enyl}; Cl; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclohex-2-enyl}; Cl; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (prop-2-enyl) cyclohex-2-enyl}; Cl; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4-ethynylcyclohex-2-enyl}; Cl; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (prop-1-ynyl) cyclohex-2-enyl}; Cl; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (prop-2-ynyl) cyclohex-2-enyl}; Cl; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclohex-3-enyl}; Cl; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclohex-3-enyl}; Cl; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4-fluorocyclohex-3-enyl}; Cl; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (prop-2-enyl) cyclohex-3-enyl}; Cl; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4-ethynylcyclohex-3-enyl}; Cl; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (prop-1-ynyl) cyclohex-3-enyl}; Cl; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (prop-2-ynyl) cyclohex-3-enyl}; Cl; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (fluoromethyl) cyclopentyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (difluoromethyl) cyclopentyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (trifluoromethyl) cyclopentyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3-ethynylcyclopentyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclopentyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclopentyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-2-ynyloxy) cyclopentyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3-ethynylcyclohexyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclohexyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclohexyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-2-ynyloxy) cyclohexyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4-fluorocyclohexyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4,4-difluorocyclohexyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4-ethynylcyclohexyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (prop-1-ynyl) cyclohexyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (prop-2-ynyl) cyclohexyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (3-methoxyprop-1-ynyl) cyclohexyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (3-dimethylaminoprop-1-ynyl) cyclohexyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (4-methoxycarbonylbut-1-ynyl) cyclohexyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{cyclopent-1-enyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclopent-1-enyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclopent-1-enyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{cyclopent-2-enyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclopent-2-enyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclopent-2-enyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{cyclopent-3-enyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclopent-3-enyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclopent-3-enyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3-ethynylcyclohex-1-enyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclohex-1-enyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclohex-1-enyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4-fluorocyclohex-1-enyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (prop-2-enyl) cyclohex-1-enyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4-ethynylcyclohex-1-enyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (prop-1-ynyl) cyclohex-1-enyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (prop-2-ynyl) cyclohex-1-enyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclohex-2-enyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclohex-2-enyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (prop-2-enyl) cyclohex-2-enyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4-ethynylcyclohex-2-enyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (prop-1-ynyl) cyclohex-2-enyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (prop-2-ynyl) cyclohex-2-enyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclohex-3-enyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclohex-3-enyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4-fluorocyclohex-3-enyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (prop-2-enyl) cyclohex-3-enyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4-ethynylcyclohex-3-enyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (prop-1-ynyl) cyclohex-3-enyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (prop-2-ynyl) cyclohex-3-enyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (fluoromethyl) cyclopentyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (difluoromethyl) cyclopentyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (trifluoromethyl) cyclopentyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3-ethynylcyclopentyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclopentyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclopentyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-2-ynyloxy) cyclopentyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3-ethynylcyclohexyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclohexyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclohexyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-2-ynyloxy) cyclohexyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4-fluorocyclohexyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4,4-difluorocyclohexyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4-ethynylcyclohexyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (prop-1-ynyl) cyclohexyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (prop-2-ynyl) cyclohexyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (3-methoxyprop-1-ynyl) cyclohexyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (3-dimethylaminoprop-1-ynyl) cyclohexyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (4-methoxycarbonylbut-1-ynyl) cyclohexyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{cyclopent-1-enyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclopent-1-enyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclopent-1-enyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{cyclopent-2-enyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclopent-2-enyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclopent-2-enyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{cyclopent-3-enyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclopent-3-enyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclopent-3-enyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3-ethynylcyclohex-1-enyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclohex-1-enyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclohex-1-enyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4-fluorocyclohex-1-enyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (prop-2-enyl) cyclohex-1-enyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4-ethynylcyclohex-1-enyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (prop-1-ynyl) cyclohex-1-enyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (prop-2-ynyl) cyclohex-1-enyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclohex-2-enyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclohex-2-enyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (prop-2-enyl) cyclohex-2-enyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4-ethynylcyclohex-2-enyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (prop-1-ynyl) cyclohex-2-enyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (prop-2-ynyl) cyclohex-2-enyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclohex-3-enyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclohex-3-enyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4-fluorocyclohex-3-enyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (prop-2-enyl) cyclohex-3-enyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4-ethynylcyclohex-3-enyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (prop-1-ynyl) cyclohex-3-enyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (prop-2-ynyl) cyclohex-3-enyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (fluoromethyl) cyclopentyl}; H; CN; 2; CF ₃ ];

[{3- (difluoromethyl) cyclopentyl}; H; CN; 2; CF ₃ ];

[{3- (trifluoromethyl) cyclopentyl}; H; CN; 2; CF ₃ ];

[{3-ethynylcyclopentyl}; H; CN; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclopentyl}; H; CN; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclopentyl}; H; CN; 2; CF ₃ ];

[{3- (prop-2-ynyloxy) cyclopentyl}; H; CN; 2; CF ₃ ];

[{3-ethynylcyclohexyl}; H; CN; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclohexyl}; H; CN; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclohexyl}; H; CN; 2; CF ₃ ];

[{3- (prop-2-ynyloxy) cyclohexyl}; H; CN; 2; CF ₃ ];

[{4-fluorocyclohexyl}; H; CN; 2; CF ₃ ];

[{4,4-difluorocyclohexyl}; H; CN; 2; CF ₃ ];

[{4-ethynylcyclohexyl}; H; CN; 2; CF ₃ ];

[{4- (prop-1-ynyl) cyclohexyl}; H; CN; 2; CF ₃ ];

[{4- (prop-2-ynyl) cyclohexyl}; H; CN; 2; CF ₃ ];

[{4- (3-methoxyprop-1-ynyl) cyclohexyl}; H; CN; 2; CF ₃ ];

[{4- (3-dimethylaminoprop-1-ynyl) cyclohexyl}; H; CN; 2; CF ₃ ];

[{4- (4-methoxycarbonylbut-1-ynyl) cyclohexyl}; H; CN; 2; CF ₃ ];

[{cyclopent-1-enyl}; H; CN; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclopent-1-enyl}; H; CN; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclopent-1-enyl}; H; CN; 2; CF ₃ ];

[{cyclopent-2-enyl}; H; CN; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclopent-2-enyl}; H; CN; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclopent-2-enyl}; H; CN; 2; CF ₃ ];

[{cyclopent-3-enyl}; H; CN; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclopent-3-enyl}; H; CN; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclopent-3-enyl}; H; CN; 2; CF ₃ ];

[{3-ethynylcyclohex-1-enyl}; H; CN; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclohex-1-enyl}; H; CN; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclohex-1-enyl}; H; CN; 2; CF ₃ ];

[{4-fluorocyclohex-1-enyl}; H; CN; 2; CF ₃ ];

[{4- (prop-2-enyl) cyclohex-1-enyl}; H; CN; 2; CF ₃ ];

[{4-ethynylcyclohex-1-enyl}; H; CN; 2; CF ₃ ];

[{4- (prop-1-ynyl) cyclohex-1-enyl}; H; CN; 2; CF ₃ ];

[{4- (prop-2-ynyl) cyclohex-1-enyl}; H; CN; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclohex-2-enyl}; H; CN; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclohex-2-enyl}; H; CN; 2; CF ₃ ];

[{4- (prop-2-enyl) cyclohex-2-enyl}; H; CN; 2; CF ₃ ];

[{4-ethynylcyclohex-2-enyl}; H; CN; 2; CF ₃ ];

[{4- (prop-1-ynyl) cyclohex-2-enyl}; H; CN; 2; CF ₃ ];

[{4- (prop-2-ynyl) cyclohex-2-enyl}; H; CN; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclohex-3-enyl}; H; CN; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclohex-3-enyl}; H; CN; 2; CF ₃ ];

[{4-fluorocyclohex-3-enyl}; H; CN; 2; CF ₃ ];

[{4- (prop-2-enyl) cyclohex-3-enyl}; H; CN; 2; CF ₃ ];

[{4-ethynylcyclohex-3-enyl}; H; CN; 2; CF ₃ ];

[{4- (prop-1-ynyl) cyclohex-3-enyl}; H; CN; 2; CF ₃ ];

[{4- (prop-2-ynyl) cyclohex-3-enyl}; H; CN; 2; CF ₃ ];

[{3- (fluoromethyl) cyclopentyl}; F; CN; 2; CF ₃ ];

[{3- (difluoromethyl) cyclopentyl}; F; CN; 2; CF ₃ ];

[{3- (trifluoromethyl) cyclopentyl}; F; CN; 2; CF ₃ ];

[{3-ethynylcyclopentyl}; F; CN; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclopentyl}; F; CN; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclopentyl}; F; CN; 2; CF ₃ ];

[{3- (prop-2-ynyloxy) cyclopentyl}; F; CN; 2; CF ₃ ];

[{3-ethynylcyclohexyl}; F; CN; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclohexyl}; F; CN; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclohexyl}; F; CN; 2; CF ₃ ];

[{3- (prop-2-ynyloxy) cyclohexyl}; F; CN; 2; CF ₃ ];

[{4-fluorocyclohexyl}; F; CN; 2; CF ₃ ];

[{4,4-difluorocyclohexyl}; F; CN; 2; CF ₃ ];

[{4-ethynylcyclohexyl}; F; CN; 2; CF ₃ ];

[{4- (prop-1-ynyl) cyclohexyl}; F; CN; 2; CF ₃ ];

[{4- (prop-2-ynyl) cyclohexyl}; F; CN; 2; CF ₃ ];

[{4- (3-methoxyprop-1-ynyl) cyclohexyl}; F; CN; 2; CF ₃ ];

[{4- (3-dimethylaminoprop-1-ynyl) cyclohexyl}; F; CN; 2; CF ₃ ];

[{4- (4-methoxycarbonylbut-1-ynyl) cyclohexyl}; F; CN; 2; CF ₃ ];

[{cyclopent-1-enyl}; F; CN; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclopent-1-enyl}; F; CN; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclopent-1-enyl}; F; CN; 2; CF ₃ ];

[{cyclopent-2-enyl}; F; CN; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclopent-2-enyl}; F; CN; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclopent-2-enyl}; F; CN; 2; CF ₃ ];

[{cyclopent-3-enyl}; F; CN; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclopent-3-enyl}; F; CN; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclopent-3-enyl}; F; CN; 2; CF ₃ ];

[{3-ethynylcyclohex-1-enyl}; F; CN; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclohex-1-enyl}; F; CN; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclohex-1-enyl}; F; CN; 2; CF ₃ ];

[{4-fluorocyclohex-1-enyl}; F; CN; 2; CF ₃ ];

[{4- (prop-2-enyl) cyclohex-1-enyl}; F; CN; 2; CF ₃ ];

[{4-ethynylcyclohex-1-enyl}; F; CN; 2; CF ₃ ];

[{4- (prop-1-ynyl) cyclohex-1-enyl}; F; CN; 2; CF ₃ ];

[{4- (prop-2-ynyl) cyclohex-1-enyl}; F; CN; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclohex-2-enyl}; F; CN; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclohex-2-enyl}; F; CN; 2; CF ₃ ];

[{4- (prop-2-enyl) cyclohex-2-enyl}; F; CN; 2; CF ₃ ];

[{4-ethynylcyclohex-2-enyl}; F; CN; 2; CF ₃ ];

[{4- (prop-1-ynyl) cyclohex-2-enyl}; F; CN; 2; CF ₃ ];

[{4- (prop-2-ynyl) cyclohex-2-enyl}; F; CN; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclohex-3-enyl}; F; CN; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclohex-3-enyl}; F; CN; 2; CF ₃ ];

[{4-fluorocyclohex-3-enyl}; F; CN; 2; CF ₃ ];

[{4- (prop-2-enyl) cyclohex-3-enyl}; F; CN; 2; CF ₃ ];

[{4-ethynylcyclohex-3-enyl}; F; CN; 2; CF ₃ ];

[{4- (prop-1-ynyl) cyclohex-3-enyl}; F; CN; 2; CF ₃ ];

[{4- (prop-2-ynyl) cyclohex-3-enyl}; F; CN; 2; CF ₃ ];

[{3- (fluoromethyl) cyclopentyl}; Cl; CN; 2; CF ₃ ];

[{3- (difluoromethyl) cyclopentyl}; Cl; CN; 2; CF ₃ ];

[{3- (trifluoromethyl) cyclopentyl}; Cl; CN; 2; CF ₃ ];

[{3-ethynylcyclopentyl}; Cl; CN; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclopentyl}; Cl; CN; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclopentyl}; Cl; CN; 2; CF ₃ ];

[{3- (prop-2-ynyloxy) cyclopentyl}; Cl; CN; 2; CF ₃ ];

[{3-ethynylcyclohexyl}; Cl; CN; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclohexyl}; Cl; CN; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclohexyl}; Cl; CN; 2; CF ₃ ];

[{3- (prop-2-ynyloxy) cyclohexyl}; Cl; CN; 2; CF ₃ ];

[{4-fluorocyclohexyl}; Cl; CN; 2; CF ₃ ];

[{4,4-difluorocyclohexyl}; Cl; CN; 2; CF ₃ ];

[{4-ethynylcyclohexyl}; Cl; CN; 2; CF ₃ ];

[{4- (prop-1-ynyl) cyclohexyl}; Cl; CN; 2; CF ₃ ];

[{4- (prop-2-ynyl) cyclohexyl}; Cl; CN; 2; CF ₃ ];

[{4- (3-methoxyprop-1-ynyl) cyclohexyl}; Cl; CN; 2; CF ₃ ];

[{4- (3-dimethylaminoprop-1-ynyl) cyclohexyl}; Cl; CN; 2; CF ₃ ];

[{4- (4-methoxycarbonylbut-1-ynyl) cyclohexyl}; Cl; CN; 2; CF ₃ ];

[{cyclopent-1-enyl}; Cl; CN; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclopent-1-enyl}; Cl; CN; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclopent-1-enyl}; Cl; CN; 2; CF ₃ ];

[{cyclopent-2-enyl}; Cl; CN; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclopent-2-enyl}; Cl; CN; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclopent-2-enyl}; Cl; CN; 2; CF ₃ ];

[{cyclopent-3-enyl}; Cl; CN; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclopent-3-enyl}; Cl; CN; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclopent-3-enyl}; Cl; CN; 2; CF ₃ ];

[{3-ethynylcyclohex-1-enyl}; Cl; CN; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclohex-1-enyl}; Cl; CN; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclohex-1-enyl}; Cl; CN; 2; CF ₃ ];

[{4-fluorocyclohex-1-enyl}; Cl; CN; 2; CF ₃ ];

[{4- (prop-2-enyl) cyclohex-1-enyl}; Cl; CN; 2; CF ₃ ];

[{4-ethynylcyclohex-1-enyl}; Cl; CN; 2; CF ₃ ];

[{4- (prop-1-ynyl) cyclohex-1-enyl}; Cl; CN; 2; CF ₃ ];

[{4- (prop-2-ynyl) cyclohex-1-enyl}; Cl; CN; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclohex-2-enyl}; Cl; CN; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclohex-2-enyl}; Cl; CN; 2; CF ₃ ];

[{4- (prop-2-enyl) cyclohex-2-enyl}; Cl; CN; 2; CF ₃ ];

[{4-ethynylcyclohex-2-enyl}; Cl; CN; 2; CF ₃ ];

[{4- (prop-1-ynyl) cyclohex-2-enyl}; Cl; CN; 2; CF ₃ ];

[{4- (prop-2-ynyl) cyclohex-2-enyl}; Cl; CN; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclohex-3-enyl}; Cl; CN; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclohex-3-enyl}; Cl; CN; 2; CF ₃ ];

[{4-fluorocyclohex-3-enyl}; Cl; CN; 2; CF ₃ ];

[{4- (prop-2-enyl) cyclohex-3-enyl}; Cl; CN; 2; CF ₃ ];

[{4-ethynylcyclohex-3-enyl}; Cl; CN; 2; CF ₃ ];

[{4- (prop-1-ynyl) cyclohex-3-enyl}; Cl; CN; 2; CF ₃ ];

[{4- (prop-2-ynyl) cyclohex-3-enyl}; Cl; CN; 2; CF ₃ ];

[{3- (fluoromethyl) cyclopentyl}; CH ₃ ; CN; 2; CF ₃ ];

[{3- (difluoromethyl) cyclopentyl}; CH ₃ ; CN; 2; CF ₃ ];

[{3- (trifluoromethyl) cyclopentyl}; CH ₃ ; CN; 2; CF ₃ ];

[{3-ethynylcyclopentyl}; CH ₃ ; CN; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclopentyl}; CH ₃ ; CN; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclopentyl}; CH ₃ ; CN; 2; CF ₃ ];

[{3- (prop-2-ynyloxy) cyclopentyl}; CH ₃ ; CN; 2; CF ₃ ];

[{3-ethynylcyclohexyl}; CH ₃ ; CN; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclohexyl}; CH ₃ ; CN; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclohexyl}; CH ₃ ; CN; 2; CF ₃ ];

[{3- (prop-2-ynyloxy) cyclohexyl}; CH ₃ ; CN; 2; CF ₃ ];

[{4-fluorocyclohexyl}; CH ₃ ; CN; 2; CF ₃ ];

[{4,4-difluorocyclohexyl}; CH ₃ ; CN; 2; CF ₃ ];

[{4-ethynylcyclohexyl}; CH ₃ ; CN; 2; CF ₃ ];

[{4- (prop-1-ynyl) cyclohexyl}; CH ₃ ; CN; 2; CF ₃ ];

[{4- (prop-2-ynyl) cyclohexyl}; CH ₃ ; CN; 2; CF ₃ ];

[{4- (3-methoxyprop-1-ynyl) cyclohexyl}; CH ₃ ; CN; 2; CF ₃ ];

[{4- (3-dimethylaminoprop-1-ynyl) cyclohexyl}; CH ₃ ; CN; 2; CF ₃ ];

[{4- (4-methoxycarbonylbut-1-ynyl) cyclohexyl}; CH ₃ ; CN; 2; CF ₃ ];

[{cyclopent-1-enyl}; CH ₃ ; CN; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclopent-1-enyl}; CH ₃ ; CN; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclopent-1-enyl}; CH ₃ ; CN; 2; CF ₃ ];

[{cyclopent-2-enyl}; CH ₃ ; CN; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclopent-2-enyl}; CH ₃ ; CN; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclopent-2-enyl}; CH ₃ ; CN; 2; CF ₃ ];

[{cyclopent-3-enyl}; CH ₃ ; CN; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclopent-3-enyl}; CH ₃ ; CN; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclopent-3-enyl}; CH ₃ ; CN; 2; CF ₃ ];

[{3-ethynylcyclohex-1-enyl}; CH ₃ ; CN; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclohex-1-enyl}; CH ₃ ; CN; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclohex-1-enyl}; CH ₃ ; CN; 2; CF ₃ ];

[{4-fluorocyclohex-1-enyl}; CH ₃ ; CN; 2; CF ₃ ];

[{4- (prop-2-enyl) cyclohex-1-enyl}; CH ₃ ; CN; 2; CF ₃ ];

[{4-ethynylcyclohex-1-enyl}; CH ₃ ; CN; 2; CF ₃ ];

[{4- (prop-1-ynyl) cyclohex-1-enyl}; CH ₃ ; CN; 2; CF ₃ ];

[{4- (prop-2-ynyl) cyclohex-1-enyl}; CH ₃ ; CN; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclohex-2-enyl}; CH ₃ ; CN; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclohex-2-enyl}; CH ₃ ; CN; 2; CF ₃ ];

[{4- (prop-2-enyl) cyclohex-2-enyl}; CH ₃ ; CN; 2; CF ₃ ];

[{4-ethynylcyclohex-2-enyl}; CH ₃ ; CN; 2; CF ₃ ];

[{4- (prop-1-ynyl) cyclohex-2-enyl}; CH ₃ ; CN; 2; CF ₃ ];

[{4- (prop-2-ynyl) cyclohex-2-enyl}; CH ₃ ; CN; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclohex-3-enyl}; CH ₃ ; CN; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclohex-3-enyl}; CH ₃ ; CN; 2; CF ₃ ];

[{4-fluorocyclohex-3-enyl}; CH ₃ ; CN; 2; CF ₃ ];

[{4- (prop-2-enyl) cyclohex-3-enyl}; CH ₃ ; CN; 2; CF ₃ ];

[{4-ethynylcyclohex-3-enyl}; CH ₃ ; CN; 2; CF ₃ ];

[{4- (prop-1-ynyl) cyclohex-3-enyl}; CH ₃ ; CN; 2; CF ₃ ];

[{4- (prop-2-ynyl) cyclohex-3-enyl}; CH ₃ ; CN; 2; CF ₃ ];

[{3- (fluoromethyl) cyclopentyl}; H; CONH ₂ ; 2; CF ₃ ];

[{3- (difluoromethyl) cyclopentyl}; H; CONH ₂ ; 2; CF ₃ ];

[{3- (trifluoromethyl) cyclopentyl}; H; CONH ₂ ; 2; CF ₃ ];

[{3-ethynylcyclopentyl}; H; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclopentyl}; H; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclopentyl}; H; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-2-ynyloxy) cyclopentyl}; H; CONH ₂ ; 2; CF ₃ ];

[{3-ethynylcyclohexyl}; H; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclohexyl}; H; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclohexyl}; H; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-2-ynyloxy) cyclohexyl}; H; CONH ₂ ; 2; CF ₃ ];

[{4-fluorocyclohexyl}; H; CONH ₂ ; 2; CF ₃ ];

[{4,4-difluorocyclohexyl}; H; CONH ₂ ; 2; CF ₃ ];

[{4-ethynylcyclohexyl}; H; CONH ₂ ; 2; CF ₃ ];

[{4- (prop-1-ynyl) cyclohexyl}; H; CONH ₂ ; 2; CF ₃ ];

[{4- (prop-2-ynyl) cyclohexyl}; H; CONH ₂ ; 2; CF ₃ ];

[{4- (3-methoxyprop-1-ynyl) cyclohexyl}; H; CONH ₂ ; 2; CF ₃ ];

[{4- (3-dimethylaminoprop-1-ynyl) cyclohexyl}; H; CONH ₂ ; 2; CF ₃ ];

[{4- (4-methoxycarbonylbut-1-ynyl) cyclohexyl}; H; CONH ₂ ; 2; CF ₃ ];

[{cyclopent-1-enyl}; H; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclopent-1-enyl}; H; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclopent-1-enyl}; H; CONH ₂ ; 2; CF ₃ ];

[{cyclopent-2-enyl}; H; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclopent-2-enyl}; H; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclopent-2-enyl}; H; CONH ₂ ; 2; CF ₃ ];

[{cyclopent-3-enyl}; H; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclopent-3-enyl}; H; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclopent-3-enyl}; H; CONH ₂ ; 2; CF ₃ ];

[{3-ethynylcyclohex-1-enyl}; H; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclohex-1-enyl}; H; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclohex-1-enyl}; H; CONH ₂ ; 2; CF ₃ ];

[{4-fluorocyclohex-1-enyl}; H; CONH ₂ ; 2; CF ₃ ];

[{4- (prop-2-enyl) cyclohex-1-enyl}; H; CONH ₂ ; 2; CF ₃ ];

[{4-ethynylcyclohex-1-enyl}; H; CONH ₂ ; 2; CF ₃ ];

[{4- (prop-1-ynyl) cyclohex-1-enyl}; H; CONH ₂ ; 2; CF ₃ ];

[{4- (prop-2-ynyl) cyclohex-1-enyl}; H; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclohex-2-enyl}; H; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclohex-2-enyl}; H; CONH ₂ ; 2; CF ₃ ];

[{4- (prop-2-enyl) cyclohex-2-enyl}; H; CONH ₂ ; 2; CF ₃ ];

[{4-ethynylcyclohex-2-enyl}; H; CONH ₂ ; 2; CF ₃ ];

[{4- (prop-1-ynyl) cyclohex-2-enyl}; H; CONH ₂ ; 2; CF ₃ ];

[{4- (prop-2-ynyl) cyclohex-2-enyl}; H; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclohex-3-enyl}; H; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclohex-3-enyl}; H; CONH ₂ ; 2; CF ₃ ];

[{4-fluorocyclohex-3-enyl}; H; CONH ₂ ; 2; CF ₃ ];

[{4- (prop-2-enyl) cyclohex-3-enyl}; H; CONH ₂ ; 2; CF ₃ ];

[{4-ethynylcyclohex-3-enyl}; H; CONH ₂ ; 2; CF ₃ ];

[{4- (prop-1-ynyl) cyclohex-3-enyl}; H; CONH ₂ ; 2; CF ₃ ];

[{4- (prop-2-ynyl) cyclohex-3-enyl}; H; CONH ₂ ; 2; CF ₃ ];

[{3- (fluoromethyl) cyclopentyl}; F; CONH ₂ ; 2; CF ₃ ];

[{3- (difluoromethyl) cyclopentyl}; F; CONH ₂ ; 2; CF ₃ ];

[{3- (trifluoromethyl) cyclopentyl}; F; CONH ₂ ; 2; CF ₃ ];

[{3-ethynylcyclopentyl}; F; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclopentyl}; F; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclopentyl}; F; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-2-ynyloxy) cyclopentyl}; F; CONH ₂ ; 2; CF ₃ ];

[{3-ethynylcyclohexyl}; F; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclohexyl}; F; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclohexyl}; F; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-2-ynyloxy) cyclohexyl}; F; CONH ₂ ; 2; CF ₃ ];

[{4-fluorocyclohexyl}; F; CONH ₂ ; 2; CF ₃ ];

[{4,4-difluorocyclohexyl}; F; CONH ₂ ; 2; CF ₃ ];

[{4-ethynylcyclohexyl}; F; CONH ₂ ; 2; CF ₃ ];

[{4- (prop-1-ynyl) cyclohexyl}; F; CONH ₂ ; 2; CF ₃ ];

[{4- (prop-2-ynyl) cyclohexyl}; F; CONH ₂ ; 2; CF ₃ ];

[{4- (3-methoxyprop-1-ynyl) cyclohexyl}; F; CONH ₂ ; 2; CF ₃ ];

[{4- (3-dimethylaminoprop-1-ynyl) cyclohexyl}; F; CONH ₂ ; 2; CF ₃ ];

[{4- (4-methoxycarbonylbut-1-ynyl) cyclohexyl}; F; CONH ₂ ; 2; CF ₃ ];

[{cyclopent-1-enyl}; F; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclopent-1-enyl}; F; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclopent-1-enyl}; F; CONH ₂ ; 2; CF ₃ ];

[{cyclopent-2-enyl}; F; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclopent-2-enyl}; F; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclopent-2-enyl}; F; CONH ₂ ; 2; CF ₃ ];

[{cyclopent-3-enyl}; F; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclopent-3-enyl}; F; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclopent-3-enyl}; F; CONH ₂ ; 2; CF ₃ ];

[{3-ethynylcyclohex-1-enyl}; F; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclohex-1-enyl}; F; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclohex-1-enyl}; F; CONH ₂ ; 2; CF ₃ ];

[{4-fluorocyclohex-1-enyl}; F; CONH ₂ ; 2; CF ₃ ];

[{4- (prop-2-enyl) cyclohex-1-enyl}; F; CONH ₂ ; 2; CF ₃ ];

[{4-ethynylcyclohex-1-enyl}; F; CONH ₂ ; 2; CF ₃ ];

[{4- (prop-1-ynyl) cyclohex-1-enyl}; F; CONH ₂ ; 2; CF ₃ ];

[{4- (prop-2-ynyl) cyclohex-1-enyl}; F; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclohex-2-enyl}; F; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclohex-2-enyl}; F; CONH ₂ ; 2; CF ₃ ];

[{4- (prop-2-enyl) cyclohex-2-enyl}; F; CONH ₂ ; 2; CF ₃ ];

[{4-ethynylcyclohex-2-enyl}; F; CONH ₂ ; 2; CF ₃ ];

[{4- (prop-1-ynyl) cyclohex-2-enyl}; F; CONH ₂ ; 2; CF ₃ ];

[{4- (prop-2-ynyl) cyclohex-2-enyl}; F; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclohex-3-enyl}; F; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclohex-3-enyl}; F; CONH ₂ ; 2; CF ₃ ];

[{4-fluorocyclohex-3-enyl}; F; CONH ₂ ; 2; CF ₃ ];

[{4- (prop-2-enyl) cyclohex-3-enyl}; F; CONH ₂ ; 2; CF ₃ ];

[{4-ethynylcyclohex-3-enyl}; F; CONH ₂ ; 2; CF ₃ ];

[{4- (prop-1-ynyl) cyclohex-3-enyl}; F; CONH ₂ ; 2; CF ₃ ];

[{4- (prop-2-ynyl) cyclohex-3-enyl}; F; CONH ₂ ; 2; CF ₃ ];

[{3- (fluoromethyl) cyclopentyl}; Cl; CONH ₂ ; 2; CF ₃ ];

[{3- (difluoromethyl) cyclopentyl}; Cl; CONH ₂ ; 2; CF ₃ ];

[{3- (trifluoromethyl) cyclopentyl}; Cl; CONH ₂ ; 2; CF ₃ ];

[{3-ethynylcyclopentyl}; Cl; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclopentyl}; Cl; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclopentyl}; Cl; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-2-ynyloxy) cyclopentyl}; Cl; CONH ₂ ; 2; CF ₃ ];

[{3-ethynylcyclohexyl}; Cl; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclohexyl}; Cl; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclohexyl}; Cl; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-2-ynyloxy) cyclohexyl}; Cl; CONH ₂ ; 2; CF ₃ ];

[{4-fluorocyclohexyl}; Cl; CONH ₂ ; 2; CF ₃ ];

[{4,4-difluorocyclohexyl}; Cl; CONH ₂ ; 2; CF ₃ ];

[{4-ethynylcyclohexyl}; Cl; CONH ₂ ; 2; CF ₃ ];

[{4- (prop-1-ynyl) cyclohexyl}; Cl; CONH ₂ ; 2; CF ₃ ];

[{4- (prop-2-ynyl) cyclohexyl}; Cl; CONH ₂ ; 2; CF ₃ ];

[{4- (3-methoxyprop-1-ynyl) cyclohexyl}; Cl; CONH ₂ ; 2; CF ₃ ];

[{4- (3-dimethylaminoprop-1-ynyl) cyclohexyl}; Cl; CONH ₂ ; 2; CF ₃ ];

[{4- (4-methoxycarbonylbut-1-ynyl) cyclohexyl}; Cl; CONH ₂ ; 2; CF ₃ ];

[{cyclopent-1-enyl}; Cl; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclopent-1-enyl}; Cl; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclopent-1-enyl}; Cl; CONH ₂ ; 2; CF ₃ ];

[{cyclopent-2-enyl}; Cl; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclopent-2-enyl}; Cl; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclopent-2-enyl}; Cl; CONH ₂ ; 2; CF ₃ ];

[{cyclopent-3-enyl}; Cl; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclopent-3-enyl}; Cl; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclopent-3-enyl}; Cl; CONH ₂ ; 2; CF ₃ ];

[{3-ethynylcyclohex-1-enyl}; Cl; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclohex-1-enyl}; Cl; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclohex-1-enyl}; Cl; CONH ₂ ; 2; CF ₃ ];

[{4-fluorocyclohex-1-enyl}; Cl; CONH ₂ ; 2; CF ₃ ];

[{4- (prop-2-enyl) cyclohex-1-enyl}; Cl; CONH ₂ ; 2; CF ₃ ];

[{4-ethynylcyclohex-1-enyl}; Cl; CONH ₂ ; 2; CF ₃ ];

[{4- (prop-1-ynyl) cyclohex-1-enyl}; Cl; CONH ₂ ; 2; CF ₃ ];

[{4- (prop-2-ynyl) cyclohex-1-enyl}; Cl; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclohex-2-enyl}; Cl; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclohex-2-enyl}; Cl; CONH ₂ ; 2; CF ₃ ];

[{4- (prop-2-enyl) cyclohex-2-enyl}; Cl; CONH ₂ ; 2; CF ₃ ];

[{4-ethynylcyclohex-2-enyl}; Cl; CONH ₂ ; 2; CF ₃ ];

[{4- (prop-1-ynyl) cyclohex-2-enyl}; Cl; CONH ₂ ; 2; CF ₃ ];

[{4- (prop-2-ynyl) cyclohex-2-enyl}; Cl; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclohex-3-enyl}; Cl; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclohex-3-enyl}; Cl; CONH ₂ ; 2; CF ₃ ];

[{4-fluorocyclohex-3-enyl}; Cl; CONH ₂ ; 2; CF ₃ ];

[{4- (prop-2-enyl) cyclohex-3-enyl}; Cl; CONH ₂ ; 2; CF ₃ ];

[{4-ethynylcyclohex-3-enyl}; Cl; CONH ₂ ; 2; CF ₃ ];

[{4- (prop-1-ynyl) cyclohex-3-enyl}; Cl; CONH ₂ ; 2; CF ₃ ];

[{4- (prop-2-ynyl) cyclohex-3-enyl}; Cl; CONH ₂ ; 2; CF ₃ ];

[{3- (fluoromethyl) cyclopentyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{3- (difluoromethyl) cyclopentyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{3- (trifluoromethyl) cyclopentyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{3-ethynylcyclopentyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclopentyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclopentyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-2-ynyloxy) cyclopentyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{3-ethynylcyclohexyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclohexyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclohexyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-2-ynyloxy) cyclohexyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{4-fluorocyclohexyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{4,4-difluorocyclohexyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{4-ethynylcyclohexyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{4- (prop-1-ynyl) cyclohexyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{4- (prop-2-ynyl) cyclohexyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{4- (3-methoxyprop-1-ynyl) cyclohexyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{4- (3-dimethylaminoprop-1-ynyl) cyclohexyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{4- (4-methoxycarbonylbut-1-ynyl) cyclohexyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{cyclopent-1-enyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclopent-1-enyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclopent-1-enyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{cyclopent-2-enyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclopent-2-enyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclopent-2-enyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{cyclopent-3-enyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclopent-3-enyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclopent-3-enyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{3-ethynylcyclohex-1-enyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclohex-1-enyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclohex-1-enyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{4-fluorocyclohex-1-enyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{4- (prop-2-enyl) cyclohex-1-enyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{4-ethynylcyclohex-1-enyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{4- (prop-1-ynyl) cyclohex-1-enyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{4- (prop-2-ynyl) cyclohex-1-enyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclohex-2-enyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclohex-2-enyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{4- (prop-2-enyl) cyclohex-2-enyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{4-ethynylcyclohex-2-enyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{4- (prop-1-ynyl) cyclohex-2-enyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{4- (prop-2-ynyl) cyclohex-2-enyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclohex-3-enyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclohex-3-enyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{4-fluorocyclohex-3-enyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{4- (prop-2-enyl) cyclohex-3-enyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{4-ethynylcyclohex-3-enyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{4- (prop-1-ynyl) cyclohex-3-enyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{4- (prop-2-ynyl) cyclohex-3-enyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{3- (fluoromethyl) cyclopentyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{3- (difluoromethyl) cyclopentyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{3- (trifluoromethyl) cyclopentyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{3-ethynylcyclopentyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclopentyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclopentyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-2-ynyloxy) cyclopentyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{3-ethynylcyclohexyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclohexyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclohexyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-2-ynyloxy) cyclohexyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{4-fluorocyclohexyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{4,4-difluorocyclohexyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{4-ethynylcyclohexyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{4- (prop-1-ynyl) cyclohexyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{4- (prop-2-ynyl) cyclohexyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{4- (3-methoxyprop-1-ynyl) cyclohexyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{4- (3-dimethylaminoprop-1-ynyl) cyclohexyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{4- (4-methoxycarbonylbut-1-ynyl) cyclohexyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{cyclopent-1-enyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclopent-1-enyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclopent-1-enyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{cyclopent-2-enyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclopent-2-enyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclopent-2-enyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{cyclopent-3-enyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclopent-3-enyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclopent-3-enyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{3-ethynylcyclohex-1-enyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclohex-1-enyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclohex-1-enyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{4-fluorocyclohex-1-enyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{4- (prop-2-enyl) cyclohex-1-enyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{4-ethynylcyclohex-1-enyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{4- (prop-1-ynyl) cyclohex-1-enyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{4- (prop-2-ynyl) cyclohex-1-enyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclohex-2-enyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclohex-2-enyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{4- (prop-2-enyl) cyclohex-2-enyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{4-ethynylcyclohex-2-enyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{4- (prop-1-ynyl) cyclohex-2-enyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{4- (prop-2-ynyl) cyclohex-2-enyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-1-ynyl) cyclohex-3-enyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{3- (prop-2-ynyl) cyclohex-3-enyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{4-fluorocyclohex-3-enyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{4- (prop-2-enyl) cyclohex-3-enyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{4-ethynylcyclohex-3-enyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{4- (prop-1-ynyl) cyclohex-3-enyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{4- (prop-2-ynyl) cyclohex-3-enyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{3- (methoxyimino) cyclopentyl}; H; H; 0; CF ₃ ];

[{3- (methoxyimino) cyclopentyl}; H; H; 2; CF ₃ ];

[{3- (methoxyimino) cyclopentyl}; H; H; 0; C ₂ F ₅ ];

[{3- (methoxyimino) cyclopentyl}; H; H; 2; C ₂ F ₅ ];

[{3- (methoxyimino) cyclopentyl}; H; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (methoxyimino) cyclopentyl}; F; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (methoxyimino) cyclopentyl}; Cl; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (methoxyimino) cyclopentyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (methoxyimino) cyclopentyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (methoxyimino) cyclopentyl}; H; CN; 2; CF ₃ ];

[{3- (methoxyimino) cyclopentyl}; F; CN; 2; CF ₃ ];

[{3- (methoxyimino) cyclopentyl}; Cl; CN; 2; CF ₃ ];

[{3- (methoxyimino) cyclopentyl}; CH ₃ ; CN; 2; CF ₃ ];

[{3- (methoxyimino) cyclopentyl}; H; CONH ₂ ; 2; CF ₃ ];

[{3- (methoxyimino) cyclopentyl}; F; CONH ₂ ; 2; CF ₃ ];

[{3- (methoxyimino) cyclopentyl}; Cl; CONH ₂ ; 2; CF ₃ ];

[{3- (methoxyimino) cyclopentyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{3- (methoxyimino) cyclopentyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{3- (ethoxyimino) cyclopentyl}; H; H; 0; CF ₃ ];

[{3- (ethoxyimino) cyclopentyl}; H; H; 2; CF ₃ ];

[{3- (ethoxyimino) cyclopentyl}; H; H; 0; C ₂ F ₅ ];

[{3- (ethoxyimino) cyclopentyl}; H; H; 2; C ₂ F ₅ ];

[{3- (ethoxyimino) cyclopentyl}; H; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (ethoxyimino) cyclopentyl}; F; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (ethoxyimino) cyclopentyl}; Cl; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (ethoxyimino) cyclopentyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (ethoxyimino) cyclopentyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (ethoxyimino) cyclopentyl}; H; CN; 2; CF ₃ ];

[{3- (ethoxyimino) cyclopentyl}; F; CN; 2; CF ₃ ];

[{3- (ethoxyimino) cyclopentyl}; Cl; CN; 2; CF ₃ ];

[{3- (ethoxyimino) cyclopentyl}; CH ₃ ; CN; 2; CF ₃ ];

[{3- (ethoxyimino) cyclopentyl}; H; CONH ₂ ; 2; CF ₃ ];

[{3- (ethoxyimino) cyclopentyl}; F; CONH ₂ ; 2; CF ₃ ];

[{3- (ethoxyimino) cyclopentyl}; Cl; CONH ₂ ; 2; CF ₃ ];

[{3- (ethoxyimino) cyclopentyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{3- (ethoxyimino) cyclopentyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{3- (methoxyimino) cyclohexyl}; H; H; 0; CF ₃ ];

[{3- (methoxyimino) cyclohexyl}; H; H; 2; CF ₃ ];

[{3- (methoxyimino) cyclohexyl}; H; H; 0; C ₂ F ₅ ];

[{3- (methoxyimino) cyclohexyl}; H; H; 2; C ₂ F ₅ ];

[{3- (methoxyimino) cyclohexyl}; H; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (methoxyimino) cyclohexyl}; F; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (methoxyimino) cyclohexyl}; Cl; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (methoxyimino) cyclohexyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (methoxyimino) cyclohexyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (methoxyimino) cyclohexyl}; H; CN; 2; CF ₃ ];

[{3- (methoxyimino) cyclohexyl}; F; CN; 2; CF ₃ ];

[{3- (methoxyimino) cyclohexyl}; Cl; CN; 2; CF ₃ ];

[{3- (methoxyimino) cyclohexyl}; CH ₃ ; CN; 2; CF ₃ ];

[{3- (methoxyimino) cyclohexyl}; H; CONH ₂ ; 2; CF ₃ ];

[{3- (methoxyimino) cyclohexyl}; F; CONH ₂ ; 2; CF ₃ ];

[{3- (methoxyimino) cyclohexyl}; Cl; CONH ₂ ; 2; CF ₃ ];

[{3- (methoxyimino) cyclohexyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{3- (methoxyimino) cyclohexyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{3- (ethoxyimino) cyclohexyl}; H; H; 0; CF ₃ ];

[{3- (ethoxyimino) cyclohexyl}; H; H; 2; CF ₃ ];

[{3- (ethoxyimino) cyclohexyl}; H; H; 0; C ₂ F ₅ ];

[{3- (ethoxyimino) cyclohexyl}; H; H; 2; C ₂ F ₅ ];

[{3- (ethoxyimino) cyclohexyl}; H; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (ethoxyimino) cyclohexyl}; F; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (ethoxyimino) cyclohexyl}; Cl; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (ethoxyimino) cyclohexyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (ethoxyimino) cyclohexyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{3- (ethoxyimino) cyclohexyl}; H; CN; 2; CF ₃ ];

[{3- (ethoxyimino) cyclohexyl}; F; CN; 2; CF ₃ ];

[{3- (ethoxyimino) cyclohexyl}; Cl; CN; 2; CF ₃ ];

[{3- (ethoxyimino) cyclohexyl}; CH ₃ ; CN; 2; CF ₃ ];

[{3- (ethoxyimino) cyclohexyl}; H; CONH ₂ ; 2; CF ₃ ];

[{3- (ethoxyimino) cyclohexyl}; F; CONH ₂ ; 2; CF ₃ ];

[{3- (ethoxyimino) cyclohexyl}; Cl; CONH ₂ ; 2; CF ₃ ];

[{3- (ethoxyimino) cyclohexyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{3- (ethoxyimino) cyclohexyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{4- (methoxyimino) cyclohexyl}; H; H; 0; CF ₃ ];

[{4- (methoxyimino) cyclohexyl}; H; H; 2; CF ₃ ];

[{4- (methoxyimino) cyclohexyl}; H; H; 0; C ₂ F ₅ ];

[{4- (methoxyimino) cyclohexyl}; H; H; 2; C ₂ F ₅ ];

[{4- (methoxyimino) cyclohexyl}; H; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (methoxyimino) cyclohexyl}; F; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (methoxyimino) cyclohexyl}; Cl; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (methoxyimino) cyclohexyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (methoxyimino) cyclohexyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (methoxyimino) cyclohexyl}; H; CN; 2; CF ₃ ];

[{4- (methoxyimino) cyclohexyl}; F; CN; 2; CF ₃ ];

[{4- (methoxyimino) cyclohexyl}; Cl; CN; 2; CF ₃ ];

[{4- (methoxyimino) cyclohexyl}; CH ₃ ; CN; 2; CF ₃ ];

[{4- (methoxyimino) cyclohexyl}; H; CONH ₂ ; 2; CF ₃ ];

[{4- (methoxyimino) cyclohexyl}; F; CONH ₂ ; 2; CF ₃ ];

[{4- (methoxyimino) cyclohexyl}; Cl; CONH ₂ ; 2; CF ₃ ];

[{4- (methoxyimino) cyclohexyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{4- (methoxyimino) cyclohexyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{4- (ethoxyimino) cyclohexyl}; H; H; 0; CF ₃ ];

[{4- (ethoxyimino) cyclohexyl}; H; H; 2; CF ₃ ];

[{4- (ethoxyimino) cyclohexyl}; H; H; 0; C ₂ F ₅ ];

[{4- (ethoxyimino) cyclohexyl}; H; H; 2; C ₂ F ₅ ];

[{4- (ethoxyimino) cyclohexyl}; H; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (ethoxyimino) cyclohexyl}; F; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (ethoxyimino) cyclohexyl}; Cl; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (ethoxyimino) cyclohexyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (ethoxyimino) cyclohexyl}; CH ₃ ; CO ₂ CH ₃ ; 2; CF ₃ ];

[{4- (ethoxyimino) cyclohexyl}; H; CN; 2; CF ₃ ];

[{4- (ethoxyimino) cyclohexyl}; F; CN; 2; CF ₃ ];

[{4- (ethoxyimino) cyclohexyl}; Cl; CN; 2; CF ₃ ];

[{4- (ethoxyimino) cyclohexyl}; CH ₃ ; CN; 2; CF ₃ ];

[{4- (ethoxyimino) cyclohexyl}; H; CONH ₂ ; 2; CF ₃ ];

[{4- (ethoxyimino) cyclohexyl}; F; CONH ₂ ; 2; CF ₃ ];

[{4- (ethoxyimino) cyclohexyl}; Cl; CONH ₂ ; 2; CF ₃ ];

[{4- (ethoxyimino) cyclohexyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ];

[{4- (ethoxyimino) cyclohexyl}; CH ₃ ; CONH ₂ ; 2; CF ₃ ].

The following are examples of compositions. The term "part (s)" means part (s) by weight. Compounds of the present invention are represented by numbers of the compounds described above.

An example of obtaining a composition 1

Nine parts of any of the present compounds (1) to (67) are dissolved in 37.5 parts of xylene and 37.5 parts of N, N-dimethylformamide. To these are added 10 parts of polyoxyethylene styrylphenyl ether and 6 parts of calcium dodecylbenzenesulfonate and mixed by thorough mixing to obtain an emulsifiable concentrate.

An example of obtaining a composition 2

Five parts of the present compound (1) and 4 parts of a compound selected from the following group [A] are dissolved in 37.5 parts of xylene and 37.5 parts of N, N-dimethylformamide. 10 parts of polyoxyethylene styrylphenyl ether and 6 parts of calcium dodecylbenzenesulfonate are added to them and mixed by thorough mixing to obtain an emulsifiable concentrate.

Group [A]:

aluminum phosphide, butathiophos, caduzafos, chloroethoxyphos, chlorfenvinphos, chlorpyrifos, chlorpyrifos-methyl, cyanophos (CYAP), diazinon, DCIP (dichlorodiisopropyl ether), dichlorfention (ECP), dichlorfos, DDVP, dimethonate, disulfonate, dimethonate, disulfonate, etoprofos, etrimphos, fenthion (MPP), phenitrotion (MEP), fostiazate, formotion, hydrogen phosphorus, isofenfos, isoxathion, malathion, mesulfenfos, methidation (DMTP), monocrotophos, frost (BRP), oxideprofos (ESP), Phosmet (PMP), pyrimifos-methyl, pyridafenthion, quinalphos, fentoat (PAP), profenofos, propaphos, prot iofos, pyraclorfos, salithion, sulphrophos, tebupirimfos, temefos, tetrachlorvinphos, terboufos, thiometon, trichlorfon (DEP), vamidotion, forat, caduzafos;

Alanicarb, Bendiocarb, Benfuracarb, BPMC, Carbaryl, Carbofuran, Carbosulfan, Cloethocarb, Ethiofencarb, Phenobarcarb, Phenothiocarb, Phenoxycarb, Furatiocarb, Isoprocarb (MIPC), Metarcarb, Methcarb, Methomel, Methylcarbyl, Oxycarbyl, Methylcarbyl, Oxycarbyl, Methylcarbyl, Oxycarbum, Methylcarbyl, Oxycarbum, Methylcarbyl, Oxycarbum, Methylcarbum, Methylcarbamide, Methylcarbamide, Methylcarbamide, Methylcarbamide, Methylcarbamide, Methomethylmethylene, thiodicarb, xylylcarb, aldicarb;

acrinatrin, allethrin, benfluthrin, beta-cyfluthrin, bifentrin, cycloprotrin, cyfluthrin, cygalotrin, cypermethrin, empentrine, deltamethrin, esfenvalerate, etofenprox, fenpropatrin, fenvalerate, flufrinprin, flufrinprin, flufrinprin, flufrinprin, flufrinprin, Resmmetrin, sigma-cypermethrin, silafluofen, teflutrin, tralomethrin, transfluthrin, tetramethrin, phenotrin, cifenotrin, alpha-cypermethrin, zeta-cypermethrin, lambda-cygalotrin, gamma-cygalotrin, furametrin, tau-2,3-fluvalin, 6-tetrafluoro- 4-methylbenzyl-2,2-dimethyl-3- (1-propenyl) cyclopropanecarboxylate, 2,3,5,6-tetrafluoro-4- (methoxymethyl) benzyl-2,2-dimethyl-3- (2-methyl-1 -propenyl) cyclopropanecarboxylate, 2,3,5,6-tetrafluoro-4- (methoxymethyl) benzyl-2,2-dimethyl-3- (2-cyano-1-propenyl) cyclopropanecarboxylate, 2,3,5,6-tetrafluoro -4- (methoxymethyl) benzyl-2,2,3,3-tetramethylcyclopropanecarboxylate;

cartap, bensultap, thiocyclam, monosultap, bisultap;

imidacloprid, nitenpyram, acetamipride, thiamethoxam, thiacloprid, dinotefuran, clothianidin;

chlorofluazuron, bistrifluuron, diafentyuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron, triazuron;

acetoprol, etiprol, fipronil, vanilliprol, pyriprol, pyrafluprol;

chromafenoside, halofenoside, methoxyphenoside, tebufenoside;

aldrin, dieldrin, dinochlor, endosulfan, methoxychlor;

nicotine sulfate;

avermectin-B, bromopropylate, buprofesin, chlorfenapyr, cyromazine, DD (1,3-dichloropropene), emamectin-benzoate, phenazaquin, flupirazofos, hydroprene, methoprene, indoxacarb, methoxadiazone, milbemycin-A, pimethrosidipyridine, spiniridin, pirindrosipridine, spiniridin, pirindrosidir, pirindrosidir, pirindrosidir, pirindrosidir, pirindrosidir, pirindrosidir, pirindrosidir, pirindrosidir, pirindrosidir, pirindrosidir, pirindrosidir, pirindrosidir, pirindrosidir, pirindrosidir, pirindrosidir, pirindrosidir , tolfenpyrad, triazamate, flubendiamide, lepimectin, arsenic acid, benclothiaz, calcium cyanamide, calcium polysulfide, chlordane, DDT, DSP, flufenerim, flonamide, flurimfen, formometanate, metam ammonium trifenomerate, methamide oliphenebimen , sulfur, metaflumizone, alcohol Amat, pirifluhinazon, spinetoram, chlorantraniliprole, tralopiril, a compound represented by the following formula (A):

where X ^a1 is methyl, chloro, bromo or fluoro, X ^a2 is fluoro, chloro, bromo, C1-C4 haloalkyl or C1-C4 haloalkoxy, X ^a3 is fluoro, chloro or bromo, X ^a4 is optionally substituted C1-C4 alkyl optionally substituted C3-C4 alkenyl, optionally substituted C3-C4 alkynyl, optionally substituted C3-C5 cycloalkyl or hydrogen, X ^a5 is hydrogen or methyl, X ^a6 is hydrogen, fluoro or chloro, and X ^a7 is hydrogen, fluoro or chloro;

a compound represented by the following formula (B):

where X ^b1 is X ^b2 —NH — C (= O), X ^b2 —C (= O) —NH — CH ₂ , X ^b3 —S (O), optionally substituted pyrrol-1-yl, optionally substituted with imidazole- 1-yl, optionally substituted pyrazol-1-yl or optionally substituted 1,2,4-triazol-1-yl, X ^b2 is optionally substituted C1-C4 haloalkyl, such as 2,2,2-trifluoroethyl, or optionally substituted C3 -C6 cycloalkyl, such as cyclopropyl, X ^b3 is optionally substituted C1-C4 alkyl, such as methyl, and X ^b4 is hydrogen, chloro, cyano or methyl;

a compound represented by the following formula (C):

where X ^c1 is optionally substituted C1-C4 alkyl, such as 3,3,3-trifluoropropyl, optionally substituted C1-C4 alkoxy, such as 2,2,2-trichloroethoxy, or optionally substituted phenyl, such as 4-cyanophenyl, X ^c2 represents methyl or trifluoromethylthio, and X ^c3 represents methyl or halogen;

acequinocyl, amitraz, benzooximate, biphenazate, bromopropylate, quinomethionate, chlorobenzylate, CPCBS (chlorphenzone), clofentesin, tsiflumetofen, keltan (dikofol), ethoxazole, fenbutatin oxide, fenropyksyksiproksimpriksipryksipryksipryksipryksipryksipryksipryksimpriksiproksimin pyridaben, pyrimidiphene, tebufenpyrad, tetradifon, spirodiclofen, spiromesifen, spiro tetramate, amidoflumet, cienopyrafen.

Formulation Example 3

Five parts of the present compound (4) and 4 parts of a compound selected from the group [A] are dissolved in 37.5 parts of xylene and 37.5 parts of N, N-dimethylformamide. To these are added 10 parts of polyoxyethylene styrylphenyl ether and 6 parts of calcium dodecylbenzenesulfonate and mixed by thorough mixing to obtain an emulsifiable concentrate.

An example of obtaining a composition 4

Five parts of the present compound (6) and 4 parts of a compound selected from the group [A] are dissolved in 37.5 parts of xylene and 37.5 parts of N, N-dimethylformamide. To these are added 10 parts of polyoxyethylene styrylphenyl ether and 6 parts of calcium dodecylbenzenesulfonate and mixed by thorough mixing to obtain an emulsifiable concentrate.

An example of obtaining a composition 5

Five parts of the present compound (7) and 4 parts of a compound selected from the group [A] are dissolved in 37.5 parts of xylene and 37.5 parts of N, N-dimethylformamide. To these are added 10 parts of polyoxyethylene styrylphenyl ether and 6 parts of calcium dodecylbenzenesulfonate and mixed by thorough mixing to obtain an emulsifiable concentrate.

Formulation Example 6

Five parts of the present compound (11) and 4 parts of a compound selected from the group [A] are dissolved in 37.5 parts of xylene and 37.5 parts of N, N-dimethylformamide. To these are added 10 parts of polyoxyethylene styrylphenyl ether and 6 parts of calcium dodecylbenzenesulfonate and mixed by thorough mixing to obtain an emulsifiable concentrate.

An example of obtaining a composition 7

Five parts of the present compound (12) and 4 parts of a compound selected from the group [A] are dissolved in 37.5 parts of xylene and 37.5 parts of N, N-dimethylformamide. To these are added 10 parts of polyoxyethylene styrylphenyl ether and 6 parts of calcium dodecylbenzenesulfonate and mixed by thorough mixing to obtain an emulsifiable concentrate.

Formulation Example 8

Five parts of the present compound (13) and 4 parts of a compound selected from the group [A] are dissolved in 37.5 parts of xylene and 37.5 parts of N, N-dimethylformamide. To these are added 10 parts of polyoxyethylene styrylphenyl ether and 6 parts of calcium dodecylbenzenesulfonate and mixed by thorough mixing to obtain an emulsifiable concentrate.

Formulation Example 9

Five parts of the present compound (18c) and 4 parts of a compound selected from the group [A] are dissolved in 37.5 parts of xylene and 37.5 parts of N, N-dimethylformamide. To these are added 10 parts of polyoxyethylene styrylphenyl ether and 6 parts of calcium dodecylbenzenesulfonate and mixed by thorough mixing to obtain an emulsifiable concentrate.

An example of obtaining a composition 10

Five parts of the present compound (18t) and 4 parts of a compound selected from the group [A] are dissolved in 37.5 parts of xylene and 37.5 parts of N, N-dimethylformamide. To these are added 10 parts of polyoxyethylene styrylphenyl ether and 6 parts of calcium dodecylbenzenesulfonate and mixed by thorough mixing to obtain an emulsifiable concentrate.

An example of obtaining a composition 11

Five parts of the present compound (20) and 4 parts of a compound selected from the group [A] are dissolved in 37.5 parts of xylene and 37.5 parts of N, N-dimethylformamide. To these are added 10 parts of polyoxyethylene styrylphenyl ether and 6 parts of calcium dodecylbenzenesulfonate and mixed by thorough mixing to obtain an emulsifiable concentrate.

Formulation Example 12

Five parts of the present compound (21) and 4 parts of a compound selected from the group [A] are dissolved in 37.5 parts of xylene and 37.5 parts of N, N-dimethylformamide. To these are added 10 parts of polyoxyethylene styrylphenyl ether and 6 parts of calcium dodecylbenzenesulfonate and mixed by thorough mixing to obtain an emulsifiable concentrate.

Formulation Example 13

Five parts of the present compound (22) and 4 parts of a compound selected from the group [A] are dissolved in 37.5 parts of xylene and 37.5 parts of N, N-dimethylformamide. To these are added 10 parts of polyoxyethylene styrylphenyl ether and 6 parts of calcium dodecylbenzenesulfonate and mixed by thorough mixing to obtain an emulsifiable concentrate.

An example of obtaining the composition 14

Five parts of the present compound (26t) and 4 parts of a compound selected from the group [A] are dissolved in 37.5 parts of xylene and 37.5 parts of N, N-dimethylformamide. To these are added 10 parts of polyoxyethylene styrylphenyl ether and 6 parts of calcium dodecylbenzenesulfonate and mixed by thorough mixing to obtain an emulsifiable concentrate.

An example of obtaining a composition 15

Five parts of the present compound (26c) and 4 parts of a compound selected from the group [A] are dissolved in 37.5 parts of xylene and 37.5 parts of N, N-dimethylformamide. To these are added 10 parts of polyoxyethylene styrylphenyl ether and 6 parts of calcium dodecylbenzenesulfonate and mixed by thorough mixing to obtain an emulsifiable concentrate.

An example of obtaining a composition 16

Five parts of the present compound (29) and 4 parts of a compound selected from the group [A] are dissolved in 37.5 parts of xylene and 37.5 parts of N, N-dimethylformamide. To these are added 10 parts of polyoxyethylene styrylphenyl ether and 6 parts of calcium dodecylbenzenesulfonate and mixed by thorough mixing to obtain an emulsifiable concentrate.

An example of obtaining a composition 17

Five parts of the present compound (30) and 4 parts of a compound selected from the group [A] are dissolved in 37.5 parts of xylene and 37.5 parts of N, N-dimethylformamide. To these are added 10 parts of polyoxyethylene styrylphenyl ether and 6 parts of calcium dodecylbenzenesulfonate and mixed by thorough mixing to obtain an emulsifiable concentrate.

An example of obtaining a composition 18

Five parts of the present compound (31) and 4 parts of a compound selected from the group [A] are dissolved in 37.5 parts of xylene and 37.5 parts of N, N-dimethylformamide. To these are added 10 parts of polyoxyethylene styrylphenyl ether and 6 parts of calcium dodecylbenzenesulfonate and mixed by thorough mixing to obtain an emulsifiable concentrate.

An example of obtaining a composition 19

Five parts of the present compound (32) and 4 parts of a compound selected from the group [A] are dissolved in 37.5 parts of xylene and 37.5 parts of N, N-dimethylformamide. To these are added 10 parts of polyoxyethylene styrylphenyl ether and 6 parts of calcium dodecylbenzenesulfonate and mixed by thorough mixing to obtain an emulsifiable concentrate.

An example of obtaining a composition 20

Five parts of the present compound (33) and 4 parts of a compound selected from the group [A] are dissolved in 37.5 parts of xylene and 37.5 parts of N, N-dimethylformamide. To these are added 10 parts of polyoxyethylene styrylphenyl ether and 6 parts of calcium dodecylbenzenesulfonate and mixed by thorough mixing to obtain an emulsifiable concentrate.

An example of obtaining a composition 21

Five parts of the present compound (34) and 4 parts of a compound selected from the group [A] are dissolved in 37.5 parts of xylene and 37.5 parts of N, N-dimethylformamide. To these are added 10 parts of polyoxyethylene styrylphenyl ether and 6 parts of calcium dodecylbenzenesulfonate and mixed by thorough mixing to obtain an emulsifiable concentrate.

An example of obtaining a composition 22

Five parts of the present compound (35) and 4 parts of a compound selected from the group [A] are dissolved in 37.5 parts of xylene and 37.5 parts of N, N-dimethylformamide. To these are added 10 parts of polyoxyethylene styrylphenyl ether and 6 parts of calcium dodecylbenzenesulfonate and mixed by thorough mixing to obtain an emulsifiable concentrate.

An example of obtaining a composition 23

Five parts of the present compound (40) and 4 parts of a compound selected from the group [A] are dissolved in 37.5 parts of xylene and 37.5 parts of N, N-dimethylformamide. To these are added 10 parts of polyoxyethylene styrylphenyl ether and 6 parts of calcium dodecylbenzenesulfonate and mixed by thorough mixing to obtain an emulsifiable concentrate.

An example of obtaining a composition 24

Five parts of the present compound (43) and 4 parts of a compound selected from the group [A] are dissolved in 37.5 parts of xylene and 37.5 parts of N, N-dimethylformamide. To these are added 10 parts of polyoxyethylene styrylphenyl ether and 6 parts of calcium dodecylbenzenesulfonate and mixed by thorough mixing to obtain an emulsifiable concentrate.

An example of obtaining a composition 25

Five parts of the present compound (44) and 4 parts of a compound selected from the group [A] are dissolved in 37.5 parts of xylene and 37.5 parts of N, N-dimethylformamide. To these are added 10 parts of polyoxyethylene styrylphenyl ether and 6 parts of calcium dodecylbenzenesulfonate and mixed by thorough mixing to obtain an emulsifiable concentrate.

An example of obtaining a composition 26

Five parts of the present compound (45) and 4 parts of a compound selected from the group [A] are dissolved in 37.5 parts of xylene and 37.5 parts of N, N-dimethylformamide. To these are added 10 parts of polyoxyethylene styrylphenyl ether and 6 parts of calcium dodecylbenzenesulfonate and mixed by thorough mixing to obtain an emulsifiable concentrate.

An example of obtaining a composition 27

Five parts of the present compound (51t) and 4 parts of a compound selected from the group [A] are dissolved in 37.5 parts of xylene and 37.5 parts of N, N-dimethylformamide. To these are added 10 parts of polyoxyethylene styrylphenyl ether and 6 parts of calcium dodecylbenzenesulfonate and mixed by thorough mixing to obtain an emulsifiable concentrate.

An example of obtaining a composition 28

Five parts of the present compound (51c) and 4 parts of a compound selected from the group [A] are dissolved in 37.5 parts of xylene and 37.5 parts of N, N-dimethylformamide. To these are added 10 parts of polyoxyethylene styrylphenyl ether and 6 parts of calcium dodecylbenzenesulfonate and mixed by thorough mixing to obtain an emulsifiable concentrate.

An example of obtaining a composition 29

Five parts of the present compound (52) and 4 parts of a compound selected from the group [A] are dissolved in 37.5 parts of xylene and 37.5 parts of N, N-dimethylformamide. To these are added 10 parts of polyoxyethylene styrylphenyl ether and 6 parts of calcium dodecylbenzenesulfonate and mixed by thorough mixing to obtain an emulsifiable concentrate.

Formulation Example 30

Five parts of the present compound (55) and 4 parts of a compound selected from the group [A] are dissolved in 37.5 parts of xylene and 37.5 parts of N, N-dimethylformamide. To these are added 10 parts of polyoxyethylene styrylphenyl ether and 6 parts of calcium dodecylbenzenesulfonate and mixed by thorough mixing to obtain an emulsifiable concentrate.

An example of obtaining a composition 31

Five parts of the present compound (59) and 4 parts of a compound selected from the group [A] are dissolved in 37.5 parts of xylene and 37.5 parts of N, N-dimethylformamide. To these are added 10 parts of polyoxyethylene styrylphenyl ether and 6 parts of calcium dodecylbenzenesulfonate and mixed by thorough mixing to obtain an emulsifiable concentrate.

An example of obtaining a composition 32

Five parts of the present compound (60) and 4 parts of a compound selected from the group [A] are dissolved in 37.5 parts of xylene and 37.5 parts of N, N-dimethylformamide. To these are added 10 parts of polyoxyethylene styrylphenyl ether and 6 parts of calcium dodecylbenzenesulfonate and mixed by thorough mixing to obtain an emulsifiable concentrate.

An example of obtaining a composition 33

Five parts of SORPOL 5060 (registered trademark of TOHO Chemical Industry Co., LTD.) Are added to 40 parts of any of the present compounds (1) to (67) and mixed thoroughly. Then, 32 parts of CARPLEX # 80 (registered trademark of Shionogi & Co., Ltd., a fine powder of synthetic anhydrous silica) and 23 parts of diatomaceous earth with a particle size of 300 mesh are added to them and mixed using a household mixer to obtain a wettable powder. .

An example of obtaining a composition 34

Three parts of any of the present compounds (1) to (67), 5 parts of a fine powder of synthetic anhydrous silica, 5 parts of sodium dodecylbenzenesulfonate, 30 parts of bentonite and 57 parts of clay are mixed by thorough mixing. An appropriate amount of water is added to the resulting mixture. The mixture was further mixed, granulated with a granulator, and then dried in air to obtain granules.

An example of obtaining a composition 35

Five and a half parts of any of the present compounds (1) to (67), 1 part of a fine powder of synthetic anhydrous silica, 1 part Dorires B (Sankyo) as a flocculant and 7 parts of clay are thoroughly mixed in a mortar and then mixed in a household mixer . To the resulting mixture was added 86.5 parts of clay cut into pieces and mixed by thorough mixing to obtain powder.

An example of obtaining a composition 36

Ten parts of any of the present compounds (1) to (67), 35 parts of carbon black containing 50% by weight of a salt of polyoxyethylene alkyl ether of ammonium sulfate relative to white carbon black, and 55 parts of water are mixed and then finely ground by wet grinding to obtain a composition.

An example of obtaining a composition 37

Zero point five tenths of any of the present compounds (1) to (67) are dissolved in 10 parts of dichloromethane. The resulting solution was mixed with 89.5 parts of Isopar M (isoparaffin: registered trademark of Exxon Chemical) to obtain an oil solution.

An example of obtaining a composition 38

Zero point one-tenths of any of the present compounds (1) to (67) and 49.9 parts of NEO-TOZOL (Chuo Kasei Co., Ltd.) are placed in an aerosol can. An aerosol valve is inserted into the container and then the container is charged with 25 parts of dimethyl ether and 25 parts of LPG. The actuating button is put on the cylinder valve to obtain an oil aerosol.

An example of obtaining a composition 39

0.6 parts of any of the present compounds (1) to (67), 0.01 parts of BHT, 5 parts of xylene, a mixture of 3.39 parts of deodorized kerosene and 1 part of emulsifier are charged into an aerosol can [Atmos 300 (registered trademark of Atmos Chemical Ltd.)] and 50 parts of distilled water. The valve is connected to the cylinder and then the cylinder is charged through the valve at elevated pressure with 40 parts of the propellant (LPG) to obtain an aqueous aerosol.

An example of obtaining a composition 40

Five parts of any of the present compounds (1) to (67) are dissolved in 80 parts of diethylene glycol monoethyl ether. Then mixed with 15 parts of propylene carbonate, to obtain a liquid composition for precisely directed processing.

An example of obtaining a composition 41

Ten parts of any of the present compounds (1) to (67) are dissolved in 70 parts of diethylene glycol monoethyl ether. Then mixed with 20 parts of 2-octyldodecanol, to obtain a liquid composition for external processing.

An example of obtaining a composition 42

To 0.5 parts of any of the present compounds (1) to (67), 60 parts of NIKKOL TEALS-42 (42% aqueous solution of triethanolamine lauryl sulfate, from Nikko Chemicals) and 20 parts of propylene glycol are added. The mixture is mixed well to obtain a homogeneous solution. Then 19.5 parts of water are added and mixed by thorough mixing to obtain a homogeneous shampoo.

An example of obtaining a composition 43

A porous ceramic plate 4.0 cm long, 0.4 cm wide and 1.2 cm thick is impregnated with a solution of 0.1 g of any of the present compounds (1) to (67) in 2 ml of propylene glycol to obtain a pesticide fumigated by heating.

An example of obtaining a composition 44

Five parts of any of the present compounds (1) to (67) and 95 parts of an ethylene-methyl methacrylate copolymer (methyl methacrylate content in the copolymer: 10% by weight, ACRYFT WD301, Sumitomo Chemical) are melted and kneaded in a hermetic pressure kneading machine (Moriyama Manufacturing Co., Ltd.). The resulting kneading product is extruded through the mold using an extruder to obtain a pressed bar 15 cm long and 3 mm in diameter.

An example of obtaining a composition 45

Five parts of any of the present compounds (1) to (67) and 95 parts of an elastic polyvinyl chloride resin are melted and kneaded in a hermetic pressure kneading machine (Moriyama Manufacturing Co., Ltd.). The resulting kneading product is extruded through the mold using an extruder to obtain a pressed bar 15 cm long and 3 mm in diameter.

The following test examples illustrate the effectiveness of the compounds of the present invention as the active ingredient of the pesticidal composition.

Test Example 1

The composition of any of the present compounds (1), (2), (4), (5), (7), (11), (12), (13), (18t), (18c), (19), ( 20), (21), (22), (25t), (25c), (26t), (26c), (27), (29), (30), (31), (32), (33) , (34), (35), (36), (38), (40), (41), (43), (47), (49), (50), (55) and (56) obtained according to an example of obtaining composition 36, was diluted, so that the concentration of the active ingredient was 500 ppm, to obtain a solution for testing.

At the same time, 50 g of fertile soil, Bonsol No.2 (manufactured by Sumitomo Chemical Co., Ltd.) was placed in a plastic cup and 10-15 grains of rice were sown in it. Rice plants were grown before the development of the second leaf and then trimmed so that they had the same height of 5 cm. The test solution was sprayed on rice plants in an amount of 20 ml / cup. After the test solution sprayed onto the rice plants dried, the rice plants were placed in a plastic cup in order to prevent the spread of the tested worms. Thirty larvae of brown rice delphacids of the first age stage were released into the cup, and the cup was closed with a lid. Then the cup was placed in a greenhouse at 25 ° C for 6 days. Then, the number of parasitic brown rice delphacid in rice plants was determined.

As a result, on plants treated with any of the present compounds (1), (2), (4), (5), (7), (11), (12), (13), (18t), (18c) , (19), (20), (21), (22), (25t), (25c), (26t), (26c), (27), (29), (30), (31), ( 32), (33), (34), (35), (36), (38), (40), (41), (43), (47), (49), (50), (55) and (56), the number of parasitic insects was 3 or less.

Test Example 2

The composition of any of the present compounds (2), (4), (5), (7), (11), (12), (13), (18t), (18c), (19), (20), ( 21), (22), (25t), (25c), (26t), (26c), (27), (29), (30), (31), (32), (33), (34) , (35), (38), (43), (47), (49), (50), (55) and (56) obtained according to the preparation example of composition 36 were diluted so that the concentration of the active ingredient was 55.6 hours / million, to obtain the test solution.

At the same time, 50 g of fertile soil, Bonsol No.2 (manufactured by Sumitomo Chemical Co., Ltd.) was placed in a plastic cup with five holes with a diameter of 5 mm in the bottom, and 10-15 grains of rice were sown in it. Rice plants were grown before the development of the second leaf and then treated with 45 ml of the test solution by plants absorbing the test solution from the bottom of the cup. Rice plants were placed in the greenhouse at 25 ° C for 6 days and then trimmed to the same height of 5 cm. Thirty first-stage brown rice delphacid larvae were released into the greenhouse at 25 ° C and left for 6 days. Then, the number of parasitic brown rice delphacid in rice plants was determined.

As a result, on plants treated with any of the present compounds (2), (4), (5), (7), (11), (12), (13), (18t), (18c), (19) , (20), (21), (22), (25t), (25c), (26t), (26c), (27), (29), (30), (31), (32), ( 33), (34), (35), (38), (43), (47), (49), (50), (55) and (56), the number of parasitic insects was 3 or less.

Test Example 3

The composition of any of the present compounds (4), (5), (7), (11), (12), (13), (18t), (18c), (19), (20), (22), ( 25t), (26t), (26c), (28), (29), (30), (31), (32), (33), (34), (35), (39), (40) , (41), (43), (49) and (50), obtained according to the preparation example 36, were diluted with water so that the concentration of the active ingredient was 500 ppm to obtain a test solution.

At the same time, a cucumber was planted in a polyethylene cup and grown until the first leaf developed. About 20 cotton aphids were placed on a cucumber so that they could parasitize on the cucumber. After a day, 20 ml / cup of test solution was sprayed onto a cucumber. Six days after spraying, the number of cotton aphids was determined.

As a result, on a plant treated with any of the present compounds (4), (5), (7), (11), (12), (13), (18t), (18c), (19), (20) , (22), (25t), (26t), (26c), (28), (29), (30), (31), (32), (33), (34), (35), ( 39), (40), (41), (43), (49) and (50), the number of parasitic insects was 3 or less.

Test Example 4

The composition of any of the present compounds (1), (4), (5), (7), (11), (12), (13), (18t), (18c), (19), (20), ( 21), (22), (24), (25t), (25c), (26t), (26c), (27), (29), (30), (31), (32), (33) , (34), (35), (40), (41), (43), (49), (50) and (55) obtained according to the preparation example 36, were diluted with water so that the concentration of the active ingredient was 500 hours / million, to obtain the test solution.

A filter paper with a diameter of 5.5 cm was spread at the bottom of a polyethylene cup having a diameter of 5.5 cm, and 0.7 ml of the test solution was added dropwise to the filter paper. As bait, 30 mg of sucrose was evenly distributed on filter paper. 10 adult female Musca domestica house flies were released into a plastic cup and the lid was closed. After 24 hours, the number of surviving Musca domestica was determined and the percentage of insect mortality was calculated.

As a result, treatment with any of the present compounds (1), (4), (5), (7), (11), (12), (13), (18t), (18c), (19), (20 ), (21), (22), (24), (25t), (25c), (26t), (26c), (27), (29), (30), (31), (32), (33), (34), (35), (40), (41), (43), (49), (50) and (55) were characterized by a mortality rate of 90% or more.

Test Example 5

The composition of any of the present compounds (4), (5), (7), (12), (13), (18t), (18c), (22), (25t), (25c), (26t), ( 26c), (29), (30), (31), (32), (33), (34), (40), (41), (43), (49) and (55) obtained according to example to obtain the composition 36, was diluted with water so that the concentration of the active ingredient was 500 ppm, to obtain the test solution.

A filter paper with a diameter of 5.5 cm was spread at the bottom of a polyethylene cup having a diameter of 5.5 cm, and 0.7 ml of the test solution was added dropwise to the filter paper. As bait, 30 mg of sucrose was evenly distributed on filter paper. 2 adult males of the red cockroach Blattalla germanica were released into a plastic cup , and the cup was closed with a lid. After 6 days, the number of survivors of Blattalla germanica was determined and the percentage of insect mortality was calculated.

As a result, treatment with any of the present compounds (4), (5), (7), (12), (13), (18t), (18c), (22), (25t), (25c), (26t ), (26c), (29), (30), (31), (32), (33), (34), (40), (41), (43), (49) and (55) was characterized 100% mortality rate.

Test Example 6

The composition of any of the present compounds (7), (11), (12), (13), (17), (18t), (18c), (22), (24), (25t), (25c), ( 26t), (26c), (27), (29), (33), (34), (35), (36), (38), (40), (41), (43), (47) , (49), (50) and (55), obtained according to the preparation example 36, were diluted with water so that the concentration of the active ingredient was 500 ppm to obtain a test solution.

0.7 ml of test solution (active ingredient concentration: 3.5 ppm) was added to 100 ml of ion-exchanged purified water. 20 larvae of the last age stage of the mosquito Culex pipiens pallens were released into the solution. After one day, the number of surviving Culex pipiens pallens was determined and the percentage of insect mortality was calculated.

As a result, treatment with any of the present compounds (7), (11), (12), (13), (17), (18t), (18c), (22), (24), (25t), (25c ), (26t), (26c), (27), (29), (33), (34), (35), (36), (38), (40), (41), (43), (47), (49), (50) and (55) were characterized by a mortality rate of 95% or more.

Test Example 7

Five milligrams of any of the present compounds (4), (7), (18t), (22), (25t), (26t), (29), (30), (31), (32), (33), (34), (35), (40), (41), (42), (43), (44) and (55) were dissolved in 10 ml of acetone. One milliliter of the acetone solution was uniformly applied to one side of the filter paper (TOYO No.2; 5 × 10 cm) so that the filter paper having a surface area of 50 cm ² was treated with 100 mg / m ^{2 of the} present compound. After drying, the filter paper was folded in half and its ends were bent to form a bag. The test ticks (necro-sucking nymphal ticks, Haemaphysalis longicornis , 10 ticks / group) were placed in a bag and the bag was closed with clamps. Two days later, the number of surviving ticks was determined and the mortality rate was calculated.

As a result, treatment with any of the present compounds (4), (7), (18t), (22), (25t), (26t), (29), (30), (31), (32), (33) , (34), (35), (40), (41), (42), (43), (44) and (55) was characterized by a mortality rate of 90%.

Industrial applicability

The compound of the present invention has an excellent effect against arthropod parasites, and therefore, it can be used as the active ingredient of the pesticidal composition.

Claims (22)

1. Halogen-containing organosulfur compound represented by the formula (I):

where m is 0 or 1, n is 0.1 or 2,
A represents a C3-C7 cycloalkyl group optionally substituted with a group selected from E1-E3 groups, or a C5-C7 cycloalkenyl group optionally substituted with a group selected from E1-E3 groups;
Q represents a C1-C5 haloalkyl group containing at least one fluorine atom;
R ¹ represents a C1-C4 chain hydrocarbon group, a halogen atom or a hydrogen atom;
R ² represents a C1-C4 chain hydrocarbon group optionally substituted with a halogen atom, a —C (= G) R ⁵ group, a cyano group, a halogen atom or a hydrogen atom;
R ³ and R ⁴ represent a hydrogen atom;
G represents an oxygen atom or a sulfur atom;
R ⁵ represents a C1-C4 alkoxy group, an amino group or a hydrogen atom; the E1 group is a monovalent group of substituents consisting of a hydrocarbon group with a C1-C6 chain, an optionally substituted group selected from the L group, a C3-C6 cycloalkyl group, optionally substituted with a halogen atom, a halogen atom, a cyano group and a hydroxyl group;
the E2 group is a group of divalent substituents in which two valencies are formed on the same atom, consisting of = O, = NO-R ⁶ , and = C (R ¹¹ ) R ¹² ;
the E3 group is a group of divalent substituents in which two valencies are formed on different atoms, consisting of a C2-C6 alkylene group, an optionally substituted group selected from the L group, a C4-C6 alkenylene group, an optionally substituted group selected from the L group, -GT ¹ - G- and -GT ¹ -GT ² -; where T ¹ and T ² are the same or different from each other and represent a methylene group or an ethylene group;
group L consists of a hydroxyl group, a C1-C4 alkoxy group optionally substituted with a halogen atom, a C3-C6 alkenyloxy group optionally substituted with a halogen atom, —C (= O) R ⁷ , —OC (= O) R ⁸ and a halogen atom;
R ⁶ represents a C1-C4 chain hydrocarbon group optionally substituted with a group selected from group L;
R ⁷ represents a hydroxyl group, a C1-C4 alkoxy group or a hydrogen atom;
R ⁸ represents a hydrogen atom; and
R ¹¹ and R ¹² represent a hydrogen atom. 2. The halogen-containing organosulfur compound according to claim 1, wherein Q is a C1-C3 haloalkyl group containing at least one fluorine atom. 3. The halogen-containing organosulfur compound according to claim 1, wherein Q is a C1-C5 fluoroalkyl group. 4. The halogen-containing organosulfur compound according to claim 1, wherein Q is a C1-C3 fluoroalkyl group. 5. The halogen-containing organosulfur compound according to any one of claims 1 to 4, where m is 0. 6. The halogen-containing organosulfur compound according to any one of claims 1 to 4, where m is 1. 7. The halogen-containing organosulfur compound according to claim 1, where n is 0. 8. The halogen-containing organosulfur compound according to claim 1, where n is 1. 9. The halogen-containing organosulfur compound according to claim 1, where n is 2. 10. The halogen-containing organosulfur compound according to claim 1, where R ² is a hydrogen atom. 11. The halogen-containing organosulfur compound according to claim 1, where R ² is a C1-C4 alkyl group. 12. The halogen-containing organosulfur compound according to claim 1, where R ² is a cyano group. 13. The halogen-containing organosulfur compound according to claim 1, where R ² is a group —C (= G) R ⁵ . 14. The halogen-containing organosulfur compound according to claim 1, wherein R ² is a —C (═G) R ⁵ group, G is an oxygen atom, and R ⁵ is an amino group. 15. The halogen-containing organosulfur compound according to claim 1, where R ² is a group —C (= G) R ⁵ , G is a sulfur atom, and R ⁵ is an amino group. 16. The halogen-containing organosulfur compound according to claim 1, wherein R ¹ is a hydrogen atom or a C1-C4 alkyl group. 17. The halogen-containing organosulfur compound according to claim 1, where R ¹ is a halogen atom. 18. The halogen-containing organosulfur compound according to claim 1, wherein A is a cyclohexyl group, an optionally substituted group selected from E1-E3 groups, or a cyclohexenyl group optionally substituted with a group selected from E1. 19. The halogen-containing organosulfur compound according to claim 1, wherein A is a cyclohexyl or cyclohexenyl group, which is optionally substituted with a monovalent group selected from the group consisting of a C2-C6 alkynyl group, optionally substituted with a group selected from the group L, a C2-C6 alkynyl group, optionally a substituted group selected from the group L, a halogen atom and a cyano group. 20. The halogen-containing organosulfur compound according to claim 1, wherein A is a cyclohexyl group, an optionally substituted group selected from the group E2. 21. A pesticidal composition that contains a halogen-containing organosulfur compound according to any one of claims 1 to 20 as an active ingredient. 22. A method of combating an arthropod parasite, which comprises applying an effective amount of a halogen-containing organosulfur compound according to any one of claims 1 to 20 to an arthropod parasite or to the place where the arthropod parasite lives.