JP2011157295A - Insect damage-controlling composition for plant seed, and method for preventing insect damage - Google Patents

Abstract

An insect control composition for plant seeds and a method for preventing insect damage that can effectively prevent various insect damages by applying them to plant seeds.
A method for preventing insect damage comprising applying a plant seed insect control composition containing at least one amide derivative represented by the general formula (1) as an active ingredient to a plant seed.

{In General Formula (1), A represents a carbon atom, an oxygen atom, a nitrogen atom, an oxidized nitrogen atom, or a sulfur atom. K, together with two carbon atoms to which A and A are bonded, benzene, pyridine, pyrazine, pyridazine, pyrazole, imidazole, oxazole, isoxazole, thiazole, isothiazole, furan, thiophene, oxadiazole, thiodiazole, triazole, etc. The nonmetallic atom group which forms the cyclic coupling group derived from is shown. }
[Selection figure] None

Description

The present invention relates to an insect control composition for plant seeds and a method for preventing insect damage.

Conventional drugs that prevent insect damage by applying to plant seeds include imidacloprid, thiamethoxam, and fipronil, which are effective in spraying, smearing, dipping or dressing treatments on seeds. It is known to exert.
Various amide derivatives having pesticidal activity are known (see, for example, Patent Documents 1 to 4).

International Publication No. 2005/21488 Pamphlet International Publication No. 2005/73165 Pamphlet International Publication No. 2006/137376 Pamphlet International Publication No. 2006/137395 Pamphlet

However, there are insect pests that are impossible or difficult to prevent with the above drugs.
An object of the present invention is to provide a plant seed insect control composition and a method for preventing insect damage, which can be applied to plant seeds to effectively prevent various insect damages.

As a result of intensive studies to solve the above problems, the present inventors have found that the aromatic carboxylic acid amide derivative represented by the general formula (1) is a novel compound not described in the literature, and the amide derivative is effective. The inventors have found that insect damage can be prevented by applying a composition contained as a component to plant seeds, and have completed the present invention.
That is, the present invention is as follows.
<1> The following general formula (1)

{In General Formula (1), A represents a carbon atom, an oxygen atom, a nitrogen atom, an oxidized nitrogen atom, or a sulfur atom. K together with the two carbon atoms to which A and A are attached, benzene, pyridine, pyridine-N-oxide, pyrimidine, pyrazine, pyridazine, triazine, pyrrole, pyrazole, imidazole, oxazole, isoxazole, thiazole, isothiazole, A group of nonmetallic atoms necessary for forming a cyclic linking group derived from furan, thiophene, oxadiazole, thiodiazole or triazole is shown.

X is a hydrogen atom, halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C9 cycloalkyl group, C3-C9 halocycloalkyl group, C2-C6 alkenyl group, C2-C6 haloalkenyl group, C2 -C6 alkynyl group, C2-C6 haloalkynyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C2-C6 alkenyloxy group, C2-C6 haloalkenyloxy group, C2-C6 alkynyloxy group, C2-C6 Haloalkynyloxy group, C3-C9 cycloalkoxy group, C3-C9 halocycloalkoxy group, C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 Alkylsulfonyl group, C1-C6 haloalkyl Sulfonyl group, C1-C6 alkylsulfonyloxy group, C1-C6 haloalkylsulfonyloxy group, C2-C7 alkylcarbonyl group, C2-C7 haloalkylcarbonyl group, C3-C7 alkenylcarbonyl group, C3-C7 haloalkenylcarbonyl group, C3- C7 alkynylcarbonyl group, C3-C7 haloalkynylcarbonyl group, C4-C10 cycloalkylcarbonyl group, C4-C10 halocycloalkylcarbonyl group, C2-C7 alkylcarbonyloxy group, C2-C7 haloalkylcarbonyloxy group, arylcarbonyloxy group C2-C7 alkoxycarbonyl group, C2-C7 haloalkoxycarbonyl group, C3-C7 alkenyloxycarbonyl group, C3-C7 haloalkenyloxycarbonyl group, C3-C7 Alkynyloxycarbonyl group, C3-C7 haloalkynyloxycarbonyl group, C4-C10 cycloalkyloxycarbonyl group, C4-C10 halocycloalkyloxycarbonyl group, C2-C7 alkylcarbonylamino group, C2-C7 haloalkylcarbonylamino group, C2-C7 alkoxycarbonylamino group, C2-C7 haloalkoxycarbonylamino group, C2-C7 alkoxycarbonyloxy group, C2-C7 haloalkoxycarbonyloxy group, arylcarbonylamino group, amino group, carbamoyl group, cyano group, hydroxy group , Pentafluorosulfanyl group, C1-C6 alkylamino group, C1-C6 haloalkylamino group, C2-C6 alkenylamino group, C2-C6 haloalkenylamino group, C2-C6 alkini Ruamino group, C2-C6 haloalkynylamino group, C3-C9 cycloalkylamino group, C3-C9 halocycloalkylamino group, C2-C7 alkylaminocarbonyl group, C2-C7 haloalkylaminocarbonyl group, C3-C7 alkenylaminocarbonyl Group, C3-C7 haloalkenylaminocarbonyl group, C3-C7 alkynylaminocarbonyl group, C3-C7 haloalkynylaminocarbonyl group, C4-C10 cycloalkylaminocarbonyl group, C4-C10 halocycloalkylaminocarbonyl group, phenyl group, Or when a heterocyclic group is shown and there are two or more X, each X may mutually be same or different.
n shows the integer of 0-4.

T represents a -C ₍₌ G ₁₎ -Q 1 or _{-C (= G 1) -G 2} Q 2,.
G ₁ and G ₂ each independently represent an oxygen atom or a sulfur atom.
Q ₁ and Q ₂ are each a hydrogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C2-C6 alkenyl group, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group, a C2-C6 haloalkynyl group, a C3- A C9 cycloalkyl group, a C3-C9 halocycloalkyl group, a benzyl group, an optionally substituted phenyl group, a naphthyl group, or an optionally substituted heterocyclic group is shown.

Y ₁ and Y ₅ each independently represent a halogen atom, a C1-C6 haloalkoxy group, or a C1-C3 haloalkyl group, and Y ₂ and Y ₄ each independently represent a hydrogen atom, a halogen atom, or a C1-C4 alkyl And Y ₃ represents a C2-C5 haloalkyl group.

In Q ₁ and Q ₂ , the optionally substituted phenyl group and optionally substituted heterocyclic group have a halogen atom, a C1-C6 alkyl group, a C1-C6 Haloalkyl group, C3-C9 cycloalkyl group, C3-C9 halocycloalkyl group, C2-C6 alkenyl group, C2-C6 haloalkenyl group, C2-C6 alkynyl group, C2-C6 haloalkynyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C2-C6 alkenyloxy group, C2-C6 haloalkenyloxy group, C2-C6 alkynyloxy group, C2-C6 haloalkynyloxy group, C3-C9 cycloalkoxy group, C3-C9 halocycloalkoxy group Group, C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfi Group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, C2-C7 alkylcarbonyl group, C2-C7 haloalkylcarbonyl group, C3-C7 alkenylcarbonyl group, C3-C7 haloalkenyl group Carbonyl group, C3-C7 alkynylcarbonyl group, C3-C7 haloalkynylcarbonyl group, C4-C10 cycloalkylcarbonyl group, C4-C10 halocycloalkylcarbonyl group, C2-C7 alkylcarbonyloxy group, C2-C7 haloalkylcarbonyloxy group C1-C6 alkylsulfonyloxy group, C1-C6 haloalkylsulfonyloxy group, C2-C7 alkoxycarbonyl group, C2-C7 haloalkoxycarbonyl group, C3-C7 alkenyloxy Carbonyl group, C3-C7 haloalkenyloxycarbonyl group, C3-C7 alkynyloxycarbonyl group, C3-C7 haloalkynyloxycarbonyl group, C4-C10 cycloalkyloxycarbonyl group, C4-C10 halocycloalkyloxycarbonyl group, C2- C7 alkylcarbonylamino group, C2-C7 haloalkylcarbonylamino group, C2-C7 alkoxycarbonylamino group, C2-C7 haloalkoxycarbonylamino group, C1-C6 alkylamino group, C1-C6 haloalkylamino group, C2-C6 alkenylamino Group, C2-C6 haloalkenylamino group, C2-C6 alkynylamino group, C2-C6 haloalkynylamino group, C3-C9 cycloalkylamino group, C3-C9 halocycloalkylamino group, C2 C7 alkylaminocarbonyl group, C2-C7 haloalkylaminocarbonyl group, C3-C7 alkenylaminocarbonyl group, C3-C7 haloalkenylaminocarbonyl group, C3-C7 alkynylaminocarbonyl group, C3-C7 haloalkynylaminocarbonyl group, C4- A C10 cycloalkylaminocarbonyl group, a C4-C10 halocycloalkylaminocarbonyl group, an amino group, a carbamoyl group, a cyano group, a nitro group, a hydroxy group, a pentafluorosulfanyl group, an optionally substituted phenyl group, and One or more substituents selected from the heterocyclic group which may have a substituent are shown, and when there are two or more substituents, each substituent may be the same or different.

Further, the heterocyclic group in X, Q ₁ and Q ₂ is a pyridyl group, a pyridine-N-oxide group, a pyrimidinyl group, a pyrazinyl group, a pyridazyl group, a furyl group, a thienyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, A thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a pyrrolyl group, an imidazolyl group, a triazolyl group, a pyrazolyl group, or a tetrazolyl group;

G ₃ represents an oxygen atom or a sulfur atom.
R ₁ and R ₂ each independently have a hydrogen atom, oxygen atom, halogen atom, hydroxy group, nitro group, nitroso group, trimethylsilyl group, t-butyldimethylsilyl group, cyano group, amino group, or substituent. An optionally substituted C1-C6 alkyl group, an optionally substituted C1-C6 haloalkyl group, a C2-C7 alkylcarbonyl group, a C2-C7 haloalkylcarbonyl group, an optionally substituted C2-C6 An alkenyl group, an optionally substituted C2-C6 haloalkenyl group, an optionally substituted C2-C6 alkynyl group, an optionally substituted C2-C6 haloalkynyl group, C2-C7 alkoxycarbonyl group, C2-C7 haloalkoxycarbonyl group, C3-C7 alkenyloxycarbonyl group, C3-C7 haloal group Nyloxycarbonyl group, C3-C7 alkynyloxycarbonyl group, C3-C7 haloalkynyloxycarbonyl group, phenoxycarbonyl group, C2-C7 alkylaminocarbonyl group, C2-C7 haloalkylaminocarbonyl group, C2-C7 alkylcarbonyloxy group, C2-C7 haloalkylcarbonyloxy group, benzoyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group , C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, a benzenesulfonyl group, benzylsulfonyl group, a benzyl group or,, -C (= O) C (= O) R 7 ( wherein, _{R 7} is C1- A C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group or a C1-C6 haloalkoxy group).
} The plant seed insect control composition which contains at least 1 sort (s) of the amide derivative represented by this as an active ingredient.

However, the case where the amide derivative represented by the general formula (1) is any one of the following (A) to (I) is excluded.
(A) In the general formula (1), K is a group of nonmetallic atoms necessary for forming a cyclic linking group derived from pyridine together with two carbon atoms to which A and A are bonded, ₁ is a halogen atom, _{Y 5} is C1-C6 haloalkoxy group, when T is _{-C (= G 1) -Q 1} .

(B) In the above general formula (1), K is pyrrole, pyrazole, imidazole, oxazole, isoxazole, thiazole, isothiazole, furan, thiophene, oxadiazole together with the two carbon atoms to which A and A are bonded. , A non-metallic atom group necessary for forming a cyclic linking group derived from thiodiazole or triazole, wherein Y ₁ and Y ₅ are each independently a halogen atom, and T is —C (═G ₁ ) — When G ₂ Q ₂ .

(C) In the above general formula (1), K is pyrrole, pyrazole, imidazole, oxazole, isoxazole, thiazole, isothiazole, furan, thiophene, oxadiazole together with the two carbon atoms to which A and A are bonded. , A non-metallic atom group necessary for forming a cyclic linking group derived from thiodiazole or triazole, wherein T is —C (═G ₁ ) —Q ₁ , Y ₁ is a halogen atom, and Y ₅ Is a halogen atom or a haloalkoxy group.
(D) The following general formula (2)

{In General Formula (2), Y _{2 to} Y ₄ , Q ₁ , G ₁ , G ₃ , R ₁ , and R ₂ are Y _{2 to} Y ₄ , Q ₁ , G ₁ , G in General Formula (1). ₃ , R ₁ , and R ₂ are synonymous with each other. Y ₁ is a halogen atom, and Y ₅ is a C1-C2 haloalkoxy group. } Is an amide derivative represented by:

(E) In the general formula (2), Y ₁ and Y ₅ are each independently a halogen atom, and Y ₃ is a C2-C3 haloalkyl group.
(F) The following general formula (3)

{In the general formula (3), _{Y 1} and _{Y 5} are each independently a halogen _atom, X 1, _{X 3} is a hydrogen atom or a fluorine atom, _{Q 1} is a _{Q 1} in the general formula (1) R ₁ is a hydrogen atom or a methyl group, and Y ₃ is a C3-C4 perfluoroalkyl group. } Is an amide derivative represented by:
(G) The following general formula (4)

{In the general formula (4), X ₁ is a fluorine atom, X ₂ , X ₃ and X ₄ are hydrogen atoms; Y ₁ and Y ₅ are different from each other and are a bromine atom or a trifluoromethoxy group; ₂ and Y ₄ are a hydrogen atom, Y ₃ is a heptafluoroisopropyl group, Q ₁ is a phenyl group or a 2-chloropyridin-3-yl group, R ₁ and R ₂ are different from each other, An atom or a methyl group.
Alternatively, X ₁ is a fluorine atom, X ₂ , X ₃ and X ₄ are hydrogen atoms, Y ₁ and Y ₅ are bromine atoms, Y ₂ and Y ₄ are hydrogen atoms, and Y ₃ is pentafluoroethyl. Q ₁ is a 2-fluorophenyl group, and R ₁ and R ₂ are each independently a hydrogen atom or a methyl group. } Is an amide derivative represented by:
(H) The following general formula (5)

{In General Formula (5), Y ₁ and Y ₅ are each independently a halogen atom, X ₁ is a hydrogen atom or a fluorine atom, Q ₂ is a 2,2,2-trichloroethyl group, 3 , 3,3-trifluoro-n-propyl group and Y ₃ is a C2-C4 haloalkyl group. } Is an amide derivative represented by:
(I) The following general formula (6)

{In General Formula (6), Y ₁ and Y ₅ are each independently a halogen atom, Q ₂ is synonymous with Q ₂ in General Formula (1), and R ₁ is a hydrogen atom or a methyl group , Y ₃ is a C3-C4 haloalkyl group. } Is an amide derivative represented by:
<2> The amide derivative represented by the general formula (1) is represented by the following general formula (7).

{In General Formula (7), n is 4, and X, Y _{1 to} Y ₅ , Q ₁ , G ₁ , G ₃ , R ₁ , and R ₂ represent X, Y ₁ to R in General Formula (1), respectively. Y ₅ , Q ₁ , G ₁ , G ₃ , R ₁ , and R ₂ are synonymous with each other. } Insect damage control composition for plant seeds as described in said <1> represented by these.
<3> The amide derivative represented by the general formula (7) is represented by the following general formula (8).

{In General Formula (8), Q ₁ represents a phenyl group which may have a substituent or a pyridyl group which may have a substituent. X ₁ , X ₂ , X ₃ and X ₄ each independently represent a hydrogen atom or a fluorine atom. R ₁ and R ₂ each independently represent a hydrogen atom or a C1-C3 alkyl group. Y ₁ and Y ₅ each independently represent a halogen atom, a C1-C3 haloalkoxy group or a C1-C3 haloalkyl group, and Y ₂ and Y ₄ each independently represent a hydrogen atom, a halogen atom or a C1-C4 alkyl group. shows, _{Y 3} represents a C3-C4 haloalkyl group.
However, when Y ₁ and Y ₅ are simultaneously halogen atoms, at least one of X ₁ and X ₂ is a fluorine atom. When Y ₁ or Y ₅ is a C1-C3 haloalkoxy group, X ₂ is a fluorine atom.
} Insect damage control composition for plant seeds as described in said <2> represented by these.

<4> The insect control composition for plant seeds according to <3>, wherein Y ₃ in the general formula (8) is a C3-C4 perfluoroalkyl group.
<5> In the general formula (8), Y ₁ and Y ₅ are each independently a chlorine atom, bromine atom, iodine atom, trifluoromethoxy group, trifluoromethyl group or pentafluoroethyl group, Y ₂ , Y ₄ is a hydrogen atom. The insect control composition for plant seeds according to <4>, wherein Y ₄ is a hydrogen atom.

<6> In the above general formula (8), X ₁ and X ₂ are each independently a hydrogen atom or a fluorine atom, and X ₃ and X ₄ are hydrogen atoms. Control composition.
<7> The plant seed insect control composition according to <6>, wherein in the general formula (8), R ₁ and R ₂ are each independently a hydrogen atom or a methyl group.

<8> In the general formula (8), Q ₁ is a phenyl group or a pyridyl group which may have a substituent selected from a halogen atom, a C1 haloalkyl group, a nitro group, and a cyano group. <7> An insect control composition for plant seeds as described in 1.
<9> The plant seed insect control composition according to <8>, wherein the number of substituents in Q ₁ is 1 or 2 in the general formula (8).

<10> In the general formula (8), Q ₁ is a phenyl group, a 2-fluorophenyl group, a 3-fluorophenyl group, a 4-fluorophenyl group, a 2-chlorophenyl group, a 3-chlorophenyl group, a 4-chlorophenyl group, 2-bromophenyl group, 3-bromophenyl group, 4-bromophenyl group, 2-iodophenyl group, 3-iodophenyl group, 4-iodophenyl group, (2-trifluoromethyl) phenyl group, (3-triphenyl) Fluoromethyl) phenyl group, (4-trifluoromethyl) phenyl group, 2-nitrophenyl group, 3-nitrophenyl group, 4-nitrophenyl group, 2-cyanophenyl group, 3-cyanophenyl group, 4-cyanophenyl Group, 2,6-difluorophenyl group, 3,4-dichlorophenyl group, 2,4-dichlorophenyl group, 2-chloro 4-fluorophenyl group, 2-chloro-4,5-difluorophenyl group, 4-bromo-2-chlorophenyl group, 2-bromo-4-chlorophenyl group, 2-bromo-4-fluorophenyl group, 2-chloro- 4-nitrophenyl group, 3,5-dicyanophenyl group, 4-cyano-2-fluorophenyl group, 2-chloro-4-cyanophenyl group, pyridin-3-yl group, 2-fluoropyridin-3-yl group 2-chloropyridin-3-yl group, 2-bromopyridin-3-yl group, 2-iodopyridin-3-yl group, 2- (trifluoromethyl) pyridin-3-yl group, 2-nitropyridine- 3-yl group, 2-cyanopyridin-3-yl group, 6-fluoropyridin-3-yl group, 6-chloropyridin-3-yl group, 6-bromopyridin-3-yl group, 6 -Iodopyridin-3-yl group, 6- (trifluoromethyl) pyridin-3-yl group, 6-nitropyridin-3-yl group, 6-cyanopyridin-3-yl group, 5-fluoropyridin-3- Yl group, 5-chloropyridin-3-yl group, 5-bromopyridin-3-yl group, 5-iodopyridin-3-yl group, 5- (trifluoromethyl) pyridin-3-yl group, 5-nitro Pyridin-3-yl group, 5-cyanopyridin-3-yl group, 4-fluoropyridin-3-yl group, 4-chloropyridin-3-yl group, 4-bromopyridin-3-yl group, 4-iodo Pyridin-3-yl group, 4- (trifluoromethyl) pyridin-3-yl group, 4-nitropyridin-3-yl group, 4-cyanopyridin-3-yl group, 2,6-dichloropyridine-3- Il group Din-3-yl N-oxide group, pyridin-4-yl group, 2-chloropyridin-4-yl group, 3-bromopyridin-4-yl group, 3,5-dichloropyridin-4-yl group, 3 -(Trifluoromethyl) pyridin-4-yl group, 2,6-dicyanopyridin-4-yl group, pyridin-4-yl N-oxide group, pyridin-2-yl group, 3-chloropyridin-2-yl <9>, which is a group, 4-bromopyridin-2-yl group, 5-iodopyridin-2-yl group, 6-chloropyridin-2-yl group, or 4-cyanopyridin-2-yl group Insect damage control composition for plant seeds.

<11> The amide derivative represented by the general formula (8) is 3-benzamide-N- (2-bromo-6-chloro-4- (perfluoropropan-2-yl) phenyl) -2-fluorobenzene. 2-amide, 2-chloro-N- (3- (2,6-dibromo-4- (perfluoropropan-2-yl) phenylcarbamoyl) -2-fluorophenyl) nicotinamide, 3- (4-cyano-N- Methylbenzamido) -N- (2,6-dibromo-4- (perfluoropropan-2-yl) phenyl) -2-fluorobenzamide, 2-chloro-N- (3- (2,6-dibromo-4 -(Perfluoropropan-2-yl) phenylcarbamoyl) -2-fluorophenyl) -N-methylnicotinamide, 3-benzamide-N- (2,6-diiodo-4- (par Fluoropropan-2-yl) phenyl) -2-fluorobenzamide, 3-benzamido-N- (2,6-dibromo-4- (perfluoropropan-2-yl) phenyl) -2-fluorobenzamide, N -(2,6-dibromo-4- (perfluoropropan-2-yl) phenyl) -2-fluoro-3- (N-methylbenzamido) benzamide, 6-chloro-N- (3- (2,6 -Dibromo-4- (perfluoropropan-2-yl) phenylcarbamoyl) -2-fluorophenyl) -N-methylnicotinamide, 3- (3-cyano-N-methylbenzamide) -N- (2,6- Dibromo-4- (perfluoropropan-2-yl) phenyl) -2-fluorobenzamide, N- (2,6-dichloro-4- (perfluoropropane- 2-yl) phenyl) -2-fluoro-3- (N-methylbenzamide) benzamide, 3- (4-cyano-N-methylbenzamide) -N- (2,6-dichloro-4- (perfluoropropane) -2-yl) phenyl) -2-fluorobenzamide, 2-chloro-N- (3- (2,6-dichloro-4- (perfluoropropan-2-yl) phenylcarbamoyl) -2-fluorophenyl) -N-methylnicotinamide, N- (2,6-diiodo-4- (perfluoropropan-2-yl) phenyl) -2-fluoro-3- (N-methylbenzamido) benzamide, 3- (4- Cyano-N-methylbenzamide) -N- (2,6-diiodo-4- (perfluoropropan-2-yl) phenyl) -2-fluorobenzamide, 3-benza Do-N- (2,6-dibromo-4- (perfluorobutan-2-yl) phenyl) -2-fluorobenzamide, N- (2,6-diiodo-4- (perfluoropropan-2-yl) ) Phenyl) -2-fluoro-3- (2-fluorobenzamido) benzamide, N- (2,6-diiodo-4- (perfluoropropan-2-yl) phenyl) -2-fluoro-3- (4) -Fluorobenzamide) benzamide, 3- (2,6-difluorobenzamide) -N- (2,6-diiodo-4- (perfluoropropan-2-yl) phenyl) -2-fluorobenzamide, N- ( 2-bromo-6-iodo-4- (perfluoropropan-2-yl) phenyl) -2-fluoro-3- (N-methylbenzamido) benzamide, N- (3- (2- Romo-6-iodo-4- (perfluoro-2-yl) phenylcarbamoyl) -2-fluoro-phenyl) -2-chloro -N- methyl nicotinamide,

3- (4-Cyanobenzamide) -N- (2,6-dibromo-4- (perfluorobutan-2-yl) phenyl) -2-fluorobenzamide, 3- (3-cyanobenzamide) -N- ( 2,6-dibromo-4- (perfluorobutan-2-yl) phenyl) -2-fluorobenzamide, N- (2,6-dibromo-4- (perfluorobutan-2-yl) phenyl) -2 -Fluoro-3- (N-methylbenzamido) benzamide, 3- (4-cyano-N-methylbenzamido) -N- (2,6-dibromo-4- (perfluorobutan-2-yl) phenyl)- 2-fluorobenzamide, 3- (3-cyano-N-methylbenzamide) -N- (2,6-dibromo-4- (perfluorobutan-2-yl) phenyl) -2-fluorobenz 6-chloro-N- (3- (2,6-dibromo-4- (perfluorobutan-2-yl) phenylcarbamoyl) -2-fluorophenyl) -N-methylnicotinamide, 3-benzamide-N -(2,6-Diiodo-4- (perfluorobutan-2-yl) phenyl) -2-fluorobenzamide, 3- (3-cyanobenzamido) -N- (2,6-diiodo-4- (per Fluorobutan-2-yl) phenyl) -2-fluorobenzamide, 3- (4-cyanobenzamido) -N- (2,6-diiodo-4- (perfluorobutan-2-yl) phenyl) -2- Fluorobenzamide, N- (2,6-diiodo-4- (perfluorobutan-2-yl) phenyl) -2-fluoro-3- (N-methylbenzamide) benzamide, -(3-cyano-N-methylbenzamide) -N- (2,6-diiodo-4- (perfluorobutan-2-yl) phenyl) -2-fluorobenzamide, 3- (4-cyano-N- Methylbenzamide) -N- (2,6-diiodo-4- (perfluorobutan-2-yl) phenyl) -2-fluorobenzamide, 3-benzamide-N- (2,6-diiodo-4- (per Fluorobutan-2-yl) phenyl) benzamide, 2-chloro-N- (3- (2,6-diiodo-4- (perfluorobutan-2-yl) phenylcarbamoyl) phenyl) nicotinamide, 6-chloro -N- (3- (2,6-diiodo-4- (perfluorobutan-2-yl) phenylcarbamoyl) phenyl) nicotinamide, 3-cyano-N- (3- (2,6 -Diiodo-4- (perfluorobutan-2-yl) phenylcarbamoyl) phenyl) benzamide, 3- (4-cyanobenzamido) -N- (2,6-diiodo-4- (perfluorobutan-2-yl) ) Phenyl) benzamide, N- (3- (2,6-diiodo-4- (perfluorobutan-2-yl) phenylcarbamoyl) phenyl) -2-fluorobenzamide, N- (2,6-diiodo-) 4- (Perfluorobutan-2-yl) phenyl) -3- (3-fluorobenzamido) benzamide, N- (2,6-diiodo-4- (perfluorobutan-2-yl) phenyl) -3- (4-fluorobenzamide) benzamide,

N- (3- (2,6-diiodo-4- (perfluorobutan-2-yl) phenylcarbamoyl) phenyl) -2,6-difluorobenzamide, N- (3- (2,6-diiodo-4 -(Perfluorobutan-2-yl) phenylcarbamoyl) phenyl) -N-methylbenzamide, 2-chloro-N- (3- (2,6-diiodo-4- (perfluorobutan-2-yl) phenyl Carbamoyl) phenyl) -N-methylnicotinamide, 6-chloro-N- (3- (2,6-diiodo-4- (perfluorobutan-2-yl) phenylcarbamoyl) phenyl) -N-methylnicotinamide, 3-cyano-N- (3- (2,6-diiodo-4- (perfluorobutan-2-yl) phenylcarbamoyl) phenyl) -N-methylbenzamide 4-cyano-N- (3- (2,6-diiodo-4- (perfluorobutan-2-yl) phenylcarbamoyl) phenyl) -N-methylbenzamide, N- (3- (2,6-diiodo -4- (Perfluorobutan-2-yl) phenylcarbamoyl) phenyl) -2-fluoro-N-methylbenzamide, N- (3- (2,6-diiodo-4- (perfluorobutan-2-yl) ) Phenylcarbamoyl) phenyl) -3-fluoro-N-methylbenzamide, N- (3- (2,6-diiodo-4- (perfluorobutan-2-yl) phenylcarbamoyl) phenyl) -4-fluoro- N-methylbenzamide, N- (3- (2,6-diiodo-4- (perfluorobutan-2-yl) phenylcarbamoyl) phenyl) -2,6-diflu Rho-N-methylbenzamide, 2-chloro-N- (3- (2,6-diiodo-4- (perfluorobutan-2-yl) phenylcarbamoyl) -2-fluorophenyl) nicotinamide, 6-chloro -N- (3- (2,6-diiodo-4- (perfluorobutan-2-yl) phenylcarbamoyl) -2-fluorophenyl) nicotinamide, N- (2,6-diiodo-4- (perfluoro) Butan-2-yl) phenyl) -2-fluoro-3- (2-fluorobenzamido) benzamide, N- (2,6-diiodo-4- (perfluorobutan-2-yl) phenyl) -2-fluoro -3- (3-Fluorobenzamido) benzamide, N- (2,6-diiodo-4- (perfluorobutan-2-yl) phenyl) -2-fluoro-3- (4 -Fluorobenzamide) benzamide, 3- (2,6-difluorobenzamide) -N- (2,6-diiodo-4- (perfluorobutan-2-yl) phenyl) -2-fluorobenzamide, 3-benzamide -N- (2,6-dibromo-4- (perfluorobutan-2-yl) phenyl) benzamide, 6-chloro-N- (3- (2,6-dibromo-4- (perfluorobutane-2) -Yl) phenylcarbamoyl) phenyl) nicotinamide, N- (3- (2,6-dibromo-4- (perfluorobutan-2-yl) phenylcarbamoyl) phenyl) -2-fluorobenzamide, 2-chloro- N- (3- (2,6-dibromo-4- (perfluorobutan-2-yl) phenylcarbamoyl) phenyl) nicotinamide,

N- (2,6-dibromo-4- (perfluorobutan-2-yl) phenyl) -3- (3-fluorobenzamido) benzamide, N- (2,6-dibromo-4- (perfluorobutane- 2-yl) phenyl) -3- (4-fluorobenzamido) benzamide, N- (3- (2,6-dibromo-4- (perfluorobutan-2-yl) phenylcarbamoyl) phenyl) -2,6 -Difluorobenzamide, 3-cyano-N- (3- (2,6-dibromo-4- (perfluorobutan-2-yl) phenylcarbamoyl) phenyl) benzamide, 3- (4-cyanobenzamide) -N -(2,6-dibromo-4- (perfluorobutan-2-yl) phenyl) benzamide, 2-chloro-N- (3- (2,6-diiodo-4- (perfluoro Butan-2-yl) phenylcarbamoyl) -2-fluorophenyl) -N-methylnicotinamide, 6-chloro-N- (3- (2,6-diiodo-4- (perfluorobutan-2-yl) phenyl Carbamoyl) -2-fluorophenyl) -N-methylnicotinamide, N- (3- (2,6-diiodo-4- (perfluorobutan-2-yl) phenylcarbamoyl) -2-fluorophenyl) -2- Fluoro-N-methylbenzamide, N- (2,6-diiodo-4- (perfluorobutan-2-yl) phenyl) -2-fluoro-3- (3-fluoro-N-methylbenzamide) benzamide, N- (2,6-diiodo-4- (perfluorobutan-2-yl) phenyl) -2-fluoro-3- (4-fluoro-N-methylbenza D) Benzamide, N- (3- (2,6-diiodo-4- (perfluorobutan-2-yl) phenylcarbamoyl) -2-fluorophenyl) -2,6-difluoro-N-methylbenzamide, N- (3- (2,6-dibromo-4- (perfluorobutan-2-yl) phenylcarbamoyl) phenyl) -N-methylbenzamide, 2-chloro-N- (3- (2,6-dibromo -4- (perfluorobutan-2-yl) phenylcarbamoyl) phenyl) -N-methylnicotinamide, 6-chloro-N- (3- (2,6-dibromo-4- (perfluorobutan-2-yl) ) Phenylcarbamoyl) phenyl) -N-methylnicotinamide, 3-cyano-N- (3- (2,6-dibromo-4- (perfluorobutan-2-yl) phenylcal Bamoyl) phenyl) -N-methylbenzamide, 4-cyano-N- (3- (2,6-dibromo-4- (perfluorobutan-2-yl) phenylcarbamoyl) phenyl) -N-methylbenzamide, N- (3- (2,6-dibromo-4- (perfluorobutan-2-yl) phenylcarbamoyl) phenyl) -2-fluoro-N-methylbenzamide, N- (3- (2,6-dibromo -4- (perfluorobutan-2-yl) phenylcarbamoyl) phenyl) -3-fluoro-N-methylbenzamide, N- (3- (2,6-dibromo-4- (perfluorobutan-2-yl) ) Phenylcarbamoyl) phenyl) -4-fluoro-N-methylbenzamide, N- (3- (2,6-dibromo-4- (perfluorobutan-2-yl) fe ) Phenyl) -2,6-difluoro -N- methyl downy Nzuamido,

2-chloro-N- (3- (2,6-dibromo-4- (perfluorobutan-2-yl) phenylcarbamoyl) -2-fluorophenyl) nicotinamide, 6-chloro-N- (3- (2 , 6-Dibromo-4- (perfluorobutan-2-yl) phenylcarbamoyl) -2-fluorophenyl) nicotinamide, N- (2,6-dibromo-4- (perfluorobutan-2-yl) phenyl) 2-fluoro-3- (2-fluorobenzamido) benzamide, N- (2,6-dibromo-4- (perfluorobutan-2-yl) phenyl) -2-fluoro-3- (3-fluorobenzamide ) Benzamide, N- (2,6-dibromo-4- (perfluorobutan-2-yl) phenyl) -2-fluoro-3- (4-fluorobenzamido) ben Amido, N- (2,6-dibromo-4- (perfluorobutan-2-yl) phenyl) -3- (2,6-difluorobenzamido) -2-fluorobenzamide, 2-chloro-N- (3 -(2,6-Diiodo-4- (perfluoropropan-2-yl) phenylcarbamoyl) -2-fluorophenyl) nicotinamide, 6-chloro-N- (3- (2,6-diiodo-4- ( Perfluoropropan-2-yl) phenylcarbamoyl) -2-fluorophenyl) nicotinamide, 3- (3-cyanobenzamido) -N- (2,6-diiodo-4- (perfluoropropan-2-yl) phenyl ) -2-Fluorobenzamide, 3- (4-cyanobenzamide) -N- (2,6-diiodo-4- (perfluoropropan-2-yl) phenyl 2-fluorobenzamide, N- (2,6-diiodo-4- (perfluoropropan-2-yl) phenyl) -2-fluoro-3- (3-fluorobenzamido) benzamide, 2-chloro-N -(3- (2,6-dibromo-4- (perfluorobutan-2-yl) phenylcarbamoyl) -2-fluorophenyl) -N-methylnicotinamide, N- (3- (2,6-dibromo- 4- (Perfluorobutan-2-yl) phenylcarbamoyl) -2-fluorophenyl) -2-fluoro-N-methylbenzamide, N- (2,6-dibromo-4- (perfluorobutan-2-yl) ) Phenyl) -2-fluoro-3- (3-fluoro-N-methylbenzamide) benzamide, N- (2,6-dibromo-4- (perfluorobutan-2-y) L) phenyl) -2-fluoro-3- (4-fluoro-N-methylbenzamido) benzamide, N- (3- (2,6-dibromo-4- (perfluorobutan-2-yl) phenylcarbamoyl) -2-fluorophenyl) -2,6-difluoro-N-methylbenzamide, 3- (3-cyano-N-methylbenzamide) -N- (2,6-diiodo-4- (perfluoropropane-2-) Yl) phenyl) -2-fluorobenzamide, N- (3- (2,6-diiodo-4- (perfluoropropan-2-yl) phenylcarbamoyl) -2-fluorophenyl) -2-fluoro-N- Methylbenzamide, N- (2,6-diiodo-4- (perfluoropropan-2-yl) phenyl) -2-fluoro-3- (3-fluoro-N-methylben Amide) base Nzuamido, 6-chloro-N-(3- (2,6-diiodo-4- (perfluoro-2-yl) phenylcarbamoyl) -2-fluorophenyl) -N- methyl-nicotinamide,

N- (2,6-diiodo-4- (perfluoropropan-2-yl) phenyl) -2-fluoro-3- (4-fluoro-N-methylbenzamido) benzamide, N- (3- (2, 6-diiodo-4- (perfluoropropan-2-yl) phenylcarbamoyl) -2-fluorophenyl) -2,6-difluoro-N-methylbenzamide, N- (2,6-dibromo-4- (per Fluoropropan-2-yl) phenyl) -2-fluoro-3- (2-fluorobenzamido) benzamide, N- (2,6-dibromo-4- (perfluoropropan-2-yl) phenyl) -2- Fluoro-3- (3-fluorobenzamide) benzamide, N- (2,6-dibromo-4- (perfluoropropan-2-yl) phenyl) -2-fluoro-3- 4-fluorobenzamido) benzamide, N- (2,6-dibromo-4- (perfluoropropan-2-yl) phenyl) -3- (2,6-difluorobenzamido) -2-fluorobenzamide, 6- Chloro-N- (3- (2,6-dibromo-4- (perfluoropropan-2-yl) phenylcarbamoyl) -2-fluorophenyl) nicotinamide, 3- (3-cyanobenzamide) -N- (2 , 6-Dibromo-4- (perfluoropropan-2-yl) phenyl) -2-fluorobenzamide, 3- (4-cyanobenzamido) -N- (2,6-dibromo-4- (perfluoropropane- 2-yl) phenyl) -2-fluorobenzamide, 2-chloro-N- (3- (2,6-diiodo-4- (perfluoropropan-2-yl) Phenylcarbamoyl) -2-fluorophenyl) -N-methylnicotinamide, N- (3- (2,6-dibromo-4- (perfluoropropan-2-yl) phenylcarbamoyl) -2-fluorophenyl) -2 -Fluoro-N-methylbenzamide, N- (2,6-dibromo-4- (perfluoropropan-2-yl) phenyl) -2-fluoro-3- (3-fluoro-N-methylbenzamide) benzamide N- (2,6-dibromo-4- (perfluoropropan-2-yl) phenyl) -2-fluoro-3- (4-fluoro-N-methylbenzamido) benzamide, N- (3- (2 , 6-Dibromo-4- (perfluoropropan-2-yl) phenylcarbamoyl) -2-fluorophenyl) -2,6-difluoro-N-methyl Benzamide, 3-benzamide-N- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethoxy) phenyl) -2-fluorobenzamide, N- (3- (2- Bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethoxy) phenylcarbamoyl) -2-fluorophenyl) -2-chloronicotinamide, N- (2-bromo-4- (perfluoropropane) -2-yl) -6- (trifluoromethoxy) phenyl) -3- (4-cyanobenzamido) -2-fluorobenzamide, 3-benzamido-N- (2-bromo-4- (perfluoropropane-2) -Yl) -6- (trifluoromethyl) phenyl) benzamide, N- (3- (2-bromo-4- (perfluoropropan-2-yl) 6- (trifluoromethyl) phenylcarbamoyl) phenyl) -2-chloronicotinamide, N- (3- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl ) Phenyl) -N-methylbenzamide, N- (3- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) -2-chloro-N -Methylnicotinamide, 3-benzamide-N- (2-chloro-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) benzamide, 2-chloro-N- (3- ( 2-chloro-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) nicotine Bromide, N-(2-bromo-4- (perfluoro-2-yl) -6- (trifluoromethyl) phenyl) -3- (3-cyano-benzamide) base Nzuamido,

N- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -3- (4-cyanobenzamido) benzamide, N- (3- (2-bromo- 4- (Perfluoropropan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) -3-cyano-N-methylbenzamide, N- (3- (2-bromo-4- (perfluoro) Propan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) -4-cyano-N-methylbenzamide, N- (3- (2-bromo-4- (perfluoropropan-2-yl) ) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) -2-fluoro-N-methylnicotinamide, N- (3- (2-bromo-4- (perfluoro) Lopan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) -N-methyl-4-nitrobenzamide, N- (3- (2-bromo-4- (perfluoropropan-2-yl) ) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) -6-chloro-N-methylnicotinamide, N- (3- (2-bromo-4- (perfluoropropan-2-yl) -6- ( Trifluoromethyl) phenylcarbamoyl) phenyl) -6-cyano-N-methylnicotinamide, N- (3- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl Carbamoyl) phenyl) -N-methyl-3-nitrobenzamide, N- (2-bromo-4- (perfluoropropan-2-yl) -6- ( Trifluoromethyl) phenyl) -N-methyl-3- (N-methylbenzamido) benzamide, N- (3-((2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoro Methyl) phenyl) (methyl) carbamoyl) phenyl) -2-chloro-N-methylnicotinamide, 2-bromo-N- (3- (2-bromo-4- (perfluoropropan-2-yl) -6- (Trifluoromethyl) phenylcarbamoyl) phenyl) nicotinamide, 2-chloro-N- (3- (2-chloro-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl ) -N-methylnicotinamide, N- (3- (2-chloro-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) fur Benzylcarbamoyl) phenyl) -4-cyano-N-methylbenzamide, 3-benzamido-N- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -4 -Fluorobenzamide, N- (5- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) -2-fluorophenyl) -2-chloronicotinamide, N- (3-((2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) (methyl) carbamoyl) phenyl) -2-chloronicotinamide, N- (2 -Bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -4-fluoro-3- (N-methylben Amido) benzamide, N- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -3- (4-cyano-N-methylbenzamide) -4-fluoro Bensamide, N- (5- (2-Bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) -2-fluorophenyl) -2-chloro-N-methylnicotine Amide, 3-benzamide-N- (4- (perfluoropropan-2-yl) -2,6-bis (trifluoromethyl) phenyl) benzamide,

2-chloro-N- (3- (4- (perfluoropropan-2-yl) -2,6-bis (trifluoromethyl) phenylcarbamoyl) phenyl) nicotinamide, N-methyl-N- (3- ( 4- (Perfluoropropan-2-yl) -2,6-bis (trifluoromethyl) phenylcarbamoyl) phenyl) benzamide, 2-chloro-N-methyl-N- (3- (4- (perfluoropropane -2-yl) -2,6-bis (trifluoromethyl) phenylcarbamoyl) phenyl) nicotinamide, 3-benzamido-N- (2-bromo-4- (perfluoropropan-2-yl) -6- ( Trifluoromethyl) phenyl) -N-methylbenzamide, N- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) ) Phenyl) -3- (3-cyanobenzamide) -N-methylbenzamide, N- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -3- (4-Cyanobenzamide) -N-methylbenzamide, N- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -3- (3-cyano-N -Methylbenzamide) -N-methylbenzamide, N- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -3- (4-cyano-N-methyl Benzamide) -N-methylbenzamide, 2-bromo-N- (3- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenylcarb Moyl) phenyl) -N-methylnicotinamide, 3-benzamide-N- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -2-fluorobenzamide, 2-Bromo-N- (3-((2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) (methyl) carbamoyl) phenyl) nicotinamide, N- (3 -(2-Bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) -2-fluorophenyl) -2-chloronicotinamide, 3-benzamide-N- (2- Iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) benzamide, 2-chloro-N- (3- (2 -Iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) nicotinamide, N- (3- (2-bromo-4- (perfluoropropan-2-yl) ) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) -4-cyano-2-fluoro-N-methylbenzamide, N- (3- (2-bromo-4- (perfluoropropan-2-yl)) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) -4-cyano-2-fluorobenzamide, 3-cyano-N- (3- (4- (perfluoropropan-2-yl) -2,6- Bis (trifluoromethyl) phenylcarbamoyl) phenyl) benzamide, 3- (4-cyanobenzamido) -N- (4- (perfluoropropaprop -2-yl) -2,6-bis (trifluoromethyl) phenyl) benzamide, 3-cyano-N-methyl-N- (3- (4- (perfluoropropan-2-yl) -2,6 -Bis (trifluoromethyl) phenylcarbamoyl) phenyl) benzamide, 4-cyano-N-methyl-N- (3- (4- (perfluoropropan-2-yl) -2,6-bis (trifluoromethyl) ) Phenylcarbamoyl) phenyl) benzamide,

N- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -3- (4-cyanobenzamido) -2-fluorobenzamide, N- (3- ( 2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) -2-fluorophenyl) -2-chloro-N-methylnicotinamide, N- (2-bromo- 4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -3- (4-cyano-N-methylbenzamido) -2-fluorobenzamide, N- (2-bromo-4- (Perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -2-fluoro-3- (N-methylbenzamide) benzamide, N- (2-bromo 4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -3- (3-cyano-N-methylbenzamide) -2-fluorobenzamide, N- (3- (2-bromo -4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) -2-chloro-4-cyano-N-methylbenzamide, 3-benzamido-N-methyl-N- (4- (Perfluoropropan-2-yl) -2,6-bis (trifluoromethyl) phenyl) benzamide, 2-chloro-N- (3- (methyl (4- (perfluoropropan-2-yl ) -2,6-bis (trifluoromethyl) phenyl) carbamoyl) phenyl) nicotinamide, 3- (3-cyanobenzamido) -N-methyl-N- (4- Perfluoropropan-2-yl) -2,6-bis (trifluoromethyl) phenyl) benzamide, 2-bromo-N- (3- (methyl (4- (perfluoropropan-2-yl) -2, 6-bis (trifluoromethyl) phenyl) carbamoyl) phenyl) nicotinamide, 2-bromo-N- (3- (4- (perfluoropropan-2-yl) -2,6-bis (trifluoromethyl) phenyl Carbamoyl) phenyl) nicotinamide, 2-bromo-N-methyl-N- (3- (4- (perfluoropropan-2-yl) -2,6-bis (trifluoromethyl) phenylcarbamoyl) phenyl) nicotinamide , 3- (4-Cyanobenzamido) -N- (2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl ) Phenyl) benzamide, 3-cyano-N- (3- (2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) benzamide, 2-bromo -N- (3- (2-Iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) nicotinamide, 4-cyano-N- (3- (2- Iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) -N-methylbenzamide, 2-chloro-N- (3- (2-iodo-4- ( Perfluoropropan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) -N-methylnicotinamide, N- (3- (2-bromide) -4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) -2-iodonicotinamide, N- (3- (2-bromo-4- (perfluoropropane-2) -Yl) -6- (trifluoromethyl) phenylcarbamoyl) -2-fluorophenyl) -N-methylnicotinamide, N- (3- (2-bromo-4- (perfluoropropan-2-yl) -6 -(Trifluoromethyl) phenylcarbamoyl) -2-fluorophenyl) -6-fluoro-N-methylnicotinamide, N- (3- (2-bromo-4- (perfluoropropan-2-yl) -6 (Trifluoromethyl) phenylcarbamoyl) -2-fluorophenyl) -4-cyano-2-fluoro-N-methylbenzamide,

N- (3- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) -2-fluorophenyl) -6-chloro-N-methylnicotinamide, N -(3- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) -2-fluorophenyl) -3,5-dicyano-N-methylbenzamide; 3-benzamido-2-fluoro-N- (4- (perfluoropropan-2-yl) -2,6-bis (trifluoromethyl) phenyl) benzamide, N- (3- (2-bromo-4- (Perfluoropropan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) -3,5-dicyano-N-methylbenzamide, 3-ben Amido-2-fluoro-N- (2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) benzamide, 2-chloro-N- (2-fluoro-3- (2-Iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) nicotinamide, 3-benzamide-N- (2-bromo-6- (perfluoroethyl) -4- (Perfluoropropan-2-yl) phenyl) -2-fluorobenzamide, 3-benzamido-N- (2-bromo-4- (perfluorobutan-2-yl) -6- (trifluoromethyl) ) Phenyl) -2-fluorobenzamide, N- (3- (2-bromo-4- (perfluorobutan-2-yl) -6- (trifluoromethyl) phen Rucarbamoyl) -2-fluorophenyl) -2-chloronicotinamide, N- (2-bromo-6- (perfluoroethyl) -4- (perfluoropropan-2-yl) phenyl) -3- (4-cyano Benzamido) -2-fluorobenzamide, N- (2-bromo-4- (perfluorobutan-2-yl) -6- (trifluoromethyl) phenyl) -2-fluoro-3- (N-methylbenzamide) Benzamide, N- (2-bromo-4- (perfluorobutan-2-yl) -6- (trifluoromethyl) phenyl) -3- (3-cyano-N-methylbenzamide) -2-fluorobenzamide N- (2-Bromo-4- (perfluorobutan-2-yl) -6- (trifluoromethyl) phenyl) -3- (4-cyano-N-methylbenz Amido) -2-fluorobenzamide, 2-fluoro-N- (2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -3- (N-methylbenzamide) Benzamide, 3- (4-cyano-N-methylbenzamide) -2-fluoro-N- (2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) benzamide N- (3- (2-Bromo-4- (perfluorobutan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) -N-methylbenzamide, 3-benzamide-N- (2 -Bromo-4- (perfluorobutan-2-yl) -6- (trifluoromethyl) phenyl) benzamide, 3-benzamido-2-fluoro-N- (2 Iodo-4- (perfluorobutan-2-yl) -6- (trifluoromethyl) phenyl) benzamide, 2-fluoro-N- (2-iodo-4- (perfluorobutan-2-yl) -6 -(Trifluoromethyl) phenyl) -3- (N-methylbenzamido) benzamide, 3- (4-cyano-N-methylbenzamido) -2-fluoro-N- (2-iodo-4- (perfluorobutane) -2-yl) -6- (trifluoromethyl) phenyl) benzamide,

3- (3-cyano-N-methylbenzamido) -2-fluoro-N- (2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) benzamide, 2- Fluoro-N- (2-fluoro-3- (2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) -N-methylbenzamide, 2-fluoro -3- (3-Fluoro-N-methylbenzamide) -N- (2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) benzamide, 2-fluoro-3 -(4-Fluoro-N-methylbenzamide) -N- (2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) Zuamide, 2,6-difluoro-N- (2-fluoro-3- (2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) -N-methyl Benzamide, 6-chloro-N- (2-fluoro-3- (2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) nicotinamide, 3- (3-Cyanobenzamide) -2-fluoro-N- (2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) benzamide, 3- (4-cyanobenzamide) -2-fluoro-N- (2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) benzamide, -Fluoro-3- (2-fluorobenzamide) -N- (2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) benzamide, 2-fluoro-3- ( 3-fluorobenzamido) -N- (2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) benzamide, N- (3- (2-bromo-4- ( Perfluoropropan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) -2-fluorophenyl) -2-fluoro-N-methylbenzamide, N- (3- (2-bromo-4- (per Fluoropropan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) -2-fluorophenyl) -2,6-difluoro-N-methylbenzamide N- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -2-fluoro-3- (3-fluoro-N-methylbenzamido) benzamide, N -(2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -2-fluoro-3- (4-fluoro-N-methylbenzamido) benzamide, N- ( 3- (2-Bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) -2-fluorophenyl) -2-chloronicotinamide, N- (3- (2- Bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) -2-fluorophenyl) -6-chloronicotinamide, -(2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -3- (3-cyanobenzamido) -2-fluorobenzamide, N- (2-bromo- 4- (Perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -2-fluoro-3- (2-fluorobenzamido) benzamide, N- (2-bromo-4- (perfluoropropane) -2-yl) -6- (trifluoromethyl) phenyl) -2-fluoro-3- (3-fluorobenzamido) benzamide, N- (2-bromo-4- (perfluoropropan-2-yl)- 6- (trifluoromethyl) phenyl) -2-fluoro-3- (4-fluorobenzamido) benzamide, N- (3- (2-bromo-4- (perfluoropropyl) Pan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) -2-fluorophenyl) -N-methylnicotinamide, 2-chloro-N- (2-fluoro-3- (2-iodo-4-) (Perfluoropropan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) -N-methylnicotinamide,

2-fluoro-3- (4-fluorobenzamide) -N- (2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) benzamide, 3- (2,6 -Difluorobenzamido) -2-fluoro-N- (2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) benzamide, 6-chloro-N- (2-fluoro -3- (2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) -N-methylnicotinamide, N- (3- (2-bromo-4 -(Perfluoropropan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) -6-chloronicotinamide, N- (3- (2-bromo 4- (Perfluoropropan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) -2-fluorobenzamide, N- (2-bromo-4- (perfluoropropan-2-yl)- 6- (Trifluoromethyl) phenyl) -3- (3-fluorobenzamido) benzamide, N- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl)- 3- (4-Fluorobenzamido) benzamide, N- (3- (2-Bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) -2,6- Difluorobenzamide, N- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -3 (2,6-difluorobenzamide) -2-fluorobenzamide, 3-fluoro-N- (3- (2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl ) Phenyl) benzamide, 3- (4-fluorobenzamide) -N- (2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) benzamide, 2-fluoro- N- (3- (2-Iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) benzamide, 2,6-difluoro-N- (3- (2 -Iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) benzamide, Loro-N- (3- (2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) nicotinamide, 6-chloro-N- (3- (2 -Iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) -N-methylnicotinamide, 3-cyano-N- (3- (2-iodo-4- (Perfluoropropan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) -N-methylbenzamide, 2-fluoro-N- (3- (2-iodo-4- (perfluoropropane- 2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) -N-methylbenzamide, 3-fluoro-N- (3- (2-iodo- -(Perfluoropropan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) -N-methylbenzamide, 4-fluoro-N- (3- (2-iodo-4- (perfluoropropane) -2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) -N-methylbenzamide, N- (3- (2-bromo-4- (perfluoropropan-2-yl) -6- ( Trifluoromethyl) phenylcarbamoyl) phenyl) -2-fluoro-N-methylbenzamide,

N- (3- (2-Bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) -3-fluoro-N-methylbenzamide, N- (3- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) -4-fluoro-N-methylbenzamide, N- (3- (2-bromo- 4- (Perfluoropropan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) -2,6-difluoro-N-methylbenzamide, 2,4-dichloro-N- (3- (2 -Iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) benzamide, 3- (2,4-dichloro Benzamido) -2-fluoro-N- (2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) benzamide, 2,6-difluoro-N- (3- ( 2-Iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) -N-methylbenzamide, 3- (2-chloro-4-fluorobenzamido) -2- Fluoro-N- (2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) benzamide, N- (3- (2-iodo-4- (perfluoropropane- 2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) -N-methylbenzamide, 3-benzamido-N- (2-iodo-4- ( -Fluorobutan-2-yl) -6- (trifluoromethyl) phenyl) benzamide, 2-chloro-N- (3- (2-iodo-4- (perfluorobutan-2-yl) -6- (trifluoro Methyl) phenylcarbamoyl) phenyl) nicotinamide, 6-chloro-N- (3- (2-iodo-4- (perfluorobutan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) nicotinamide 3-cyano-N- (3- (2-iodo-4- (perfluorobutan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) benzamide, 3- (4-cyanobenzamide) -N- (2-iodo-4- (perfluorobutan-2-yl) -6- (trifluoromethyl) phenyl) benzamide, 2-phenyl Fluoro-N- (3- (2-iodo-4- (perfluorobutan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) benzamide, 3-fluoro-N- (3- (2 -Iodo-4- (perfluorobutan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) benzamide, 3- (4-fluorobenzamido) -N- (2-iodo-4- (per Fluorobutan-2-yl) -6- (trifluoromethyl) phenyl) benzamide, 2,6-difluoro-N- (3- (2-iodo-4- (perfluorobutan-2-yl) -6 (Trifluoromethyl) phenylcarbamoyl) phenyl) benzamide, N- (3- (2-iodo-4- (perfluorobutan-2-yl) -6- (trifluorome L) phenylcarbamoyl) phenyl) -N-methylbenzamide, 2-chloro-N- (3- (2-iodo-4- (perfluorobutan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) Phenyl) -N-methylnicotinamide, 3-cyano-N- (3- (2-iodo-4- (perfluorobutan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) -N- Methylbenzamide, 4-cyano-N- (3- (2-iodo-4- (perfluorobutan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) -N-methylbenzamide,

3-Fluoro-N- (3- (2-iodo-4- (perfluorobutan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) -N-methylbenzamide, 4-fluoro-N -(3- (2-iodo-4- (perfluorobutan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) -N-methylbenzamide, N- (3- (2-bromo- 4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) -2-fluorophenyl) -N-methylisonicotinamide, 3-((3- (2-bromo-4- ( Perfluoropropan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) -2-fluorophenyl) (methyl) carbamoyl) pyridine 1-oxy Sid, 4-((3- (2-Bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) -2-fluorophenyl) (methyl) carbamoyl) pyridine 1-oxide 2-chloro-4-fluoro-N- (3- (2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) benzamide, N- (3 -(2-Bromo-4- (perfluorobutan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) -2-chloronicotinamide, N- (2-bromo-4- (perfluorobutane) -2-yl) -6- (trifluoromethyl) phenyl) -3- (3-cyanobenzamido) benzamide, N- (3- (2-bromo-4- (Perfluorobutan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) -2-fluorobenzamide, N- (2-bromo-4- (perfluorobutan-2-yl) -6 (Trifluoromethyl) phenyl) -3- (3-fluorobenzamido) benzamide, N- (3- (2-bromo-4- (perfluorobutan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl ) Phenyl) -6-chloronicotinamide, N- (2-bromo-4- (perfluorobutan-2-yl) -6- (trifluoromethyl) phenyl) -3- (4-cyanobenzamido) benzamide, N- (2-bromo-4- (perfluorobutan-2-yl) -6- (trifluoromethyl) phenyl) -3- (4-fluorobenza D) Benzamide, N- (3- (2-Bromo-4- (perfluorobutan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) -2,6-difluorobenzamide, N- (3- (2-Bromo-4- (perfluorobutan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) -2-chloro-N-methylnicotinamide, N- (3- (2 -Bromo-4- (perfluorobutan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) -3-cyano-N-methylbenzamide, N- (3- (2-bromo-4- (Perfluorobutan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) -2-fluoro-N-methylbenzamide, N- (3- (2 Bromo-4- (perfluorobutan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) -3-fluoro-N-methylbenzamide, N- (3- (2-bromo-4- ( Perfluorobutan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) -6-chloro-N-methylnicotinamide, N- (3- (2-bromo-4- (perfluorobutane-2) -Yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) -4-cyano-N-methylbenzamide;

N- (3- (2-bromo-4- (perfluorobutan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) -4-fluoro-N-methylbenzamide, N- (3- (2-Bromo-4- (perfluorobutan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) -2,6-difluoro-N-methylbenzamide, 6-chloro-N- (2 -Fluoro-3- (2-iodo-4- (perfluorobutan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) nicotinamide, 3- (3-cyanobenzamido) -2-fluoro- N- (2-iodo-4- (perfluorobutan-2-yl) -6- (trifluoromethyl) phenyl) benzamide, 3- (4-cyanobenzamido ) -2-Fluoro-N- (2-iodo-4- (perfluorobutan-2-yl) -6- (trifluoromethyl) phenyl) benzamide, 2-fluoro-3- (2-fluorobenzamide)- N- (2-iodo-4- (perfluorobutan-2-yl) -6- (trifluoromethyl) phenyl) benzamide, 2-fluoro-3- (3-fluorobenzamide) -N- (2-iodo -4- (perfluorobutan-2-yl) -6- (trifluoromethyl) phenyl) benzamide, 2-fluoro-3- (4-fluorobenzamide) -N- (2-iodo-4- (perfluoro) Butan-2-yl) -6- (trifluoromethyl) phenyl) benzamide, 3- (2,6-difluorobenzamido) -2-fluoro-N- (2-iodo-4- ( -Fluorobutan-2-yl) -6- (trifluoromethyl) phenyl) benzamide, N- (3- (2-bromo-4- (perfluorobutan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl ) -2-Fluorophenyl) -6-chloronicotinamide, N- (2-bromo-4- (perfluorobutan-2-yl) -6- (trifluoromethyl) phenyl) -3- (3-cyanobenzamide ) -2-fluorobenzamide, N- (2-bromo-4- (perfluorobutan-2-yl) -6- (trifluoromethyl) phenyl) -3- (4-cyanobenzamido) -2-fluorobenzene Nsamide, N- (2-bromo-4- (perfluorobutan-2-yl) -6- (trifluoromethyl) phenyl) -2-fluoro-3- (2-fur Luobenzamide) benzamide, N- (2-bromo-4- (perfluorobutan-2-yl) -6- (trifluoromethyl) phenyl) -2-fluoro-3- (3-fluorobenzamide) benzamide N- (2-bromo-4- (perfluorobutan-2-yl) -6- (trifluoromethyl) phenyl) -2-fluoro-3- (4-fluorobenzamido) benzamide, N- (2- Bromo-4- (perfluorobutan-2-yl) -6- (trifluoromethyl) phenyl) -3- (2,6-difluorobenzamido) -2-fluorobenzamide, 2-chloro-N- (2- Fluoro-3- (2-iodo-4- (perfluorobutan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) -N-methylnicoti Amido, 6-chloro-N- (2-fluoro-3- (2-iodo-4- (perfluorobutan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) -N-methylnicotinamide 3- (3-cyano-N-methylbenzamide) -2-fluoro-N- (2-iodo-4- (perfluorobutan-2-yl) -6- (trifluoromethyl) phenyl) benzamide, 2 -Fluoro-N- (2-fluoro-3- (2-iodo-4- (perfluorobutan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) -N-methylbenzamide;

2-fluoro-3- (3-fluoro-N-methylbenzamide) -N- (2-iodo-4- (perfluorobutan-2-yl) -6- (trifluoromethyl) phenyl) benzamide, 2- Fluoro-3- (4-fluoro-N-methylbenzamide) -N- (2-iodo-4- (perfluorobutan-2-yl) -6- (trifluoromethyl) phenyl) benzamide, 2-chloro- 4,5-difluoro-N- (3- (2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) benzamide, 2-chloro-4-fluoro -N- (3- (2-Iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) -N-methylbennes , N- (3- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) -2-chloro-4-fluorobenzamide, 2-chloro -N- (3- (2-Iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) benzamide, 3- (2-chlorobenzamido) -2-fluoro -N- (2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) benzamide, 2-chloro-N- (3- (2-iodo-4- (per Fluoropropan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) -N-methylbenzamide, N- (3- (2-bromo-4- (par Fluoropropan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) -2-chlorobenzamide, 2-chloro-N- (3- (2-iodo-4- (perfluoropropan-2-yl) ) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) -4-nitrobenzamide, N- (2-fluoro-3- (2-iodo-4- (perfluoropropan-2-yl) -6- ( Trifluoromethyl) phenylcarbamoyl) phenyl) -N-methylnicotinamide, 3-((2-fluoro-3- (2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl)) Phenylcarbamoyl) phenyl) (methyl) carbamoyl) pyridine 1-oxide, 4-bromo-2-chloro-N- (3- (2-iodine) -4- (Perfluoropropan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) benzamide, 2-bromo-4-chloro-N- (3- (2-iodo-4- (per Fluoropropan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) benzamide, 2-bromo-4-fluoro-N- (3- (2-iodo-4- (perfluoropropan-2-) Yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) benzamide, 2-fluoro-3- (3-fluoro-N-methylbenzamide) -N- (2-iodo-4- (perfluoropropane-2) -Yl) -6- (trifluoromethyl) phenyl) -N-methylbenzamide, N- (2-bromo-4- (perfluoropropane-2-) Yl) -6- (trifluoromethyl) phenyl) -2-fluoro-N-methyl-3- (N-methylbenzamido) benzamide or N- (2-chloro-4- (perfluoropropan-2-yl) Ill) -6- (trifluoromethyl) phenyl) -2-fluoro-3- (N-methylbenzamido) benzamide, The insect control composition for plant seeds according to <10> above.

<12> In the general formula (7), at least one of X is a chlorine atom, a bromine atom, an iodine atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C9 cycloalkyl group, or a C3-C9. Halocycloalkyl group, C2-C6 alkenyl group, C2-C6 haloalkenyl group, C2-C6 alkynyl group, C2-C6 haloalkynyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C2-C6 alkenyloxy group , C2-C6 haloalkenyloxy group, C2-C6 alkynyloxy group, C2-C6 haloalkynyloxy group, C3-C9 cycloalkoxy group, C3-C9 halocycloalkoxy group, C1-C6 alkylthio group, C1-C6 haloalkylthio Group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfur Inyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, C1-C6 alkylsulfonyloxy group, C1-C6 haloalkylsulfonyloxy group, C2-C7 alkylcarbonyl group, C2-C7 haloalkylcarbonyl group, C3-C7 Alkenylcarbonyl group, C3-C7 haloalkenylcarbonyl group, C3-C7 alkynylcarbonyl group, C3-C7 haloalkynylcarbonyl group, C4-C10 cycloalkylcarbonyl group, C4-C10 halocycloalkylcarbonyl group, C2-C7 alkylcarbonyloxy Group, C2-C7 haloalkylcarbonyloxy group, arylcarbonyloxy group, C2-C7 alkoxycarbonyl group, C2-C7 haloalkoxycarbonyl group, C3-C7 alkenyloxycarbo group Group, C3-C7 haloalkenyloxycarbonyl group, C3-C7 alkynyloxycarbonyl group, C3-C7 haloalkynyloxycarbonyl group, C4-C10 cycloalkyloxycarbonyl group, C4-C10 halocycloalkyloxycarbonyl group, C2- C7 alkylcarbonylamino group, C2-C7 haloalkylcarbonylamino group, C2-C7 alkoxycarbonylamino group, C2-C7 haloalkoxycarbonylamino group, C2-C7 alkoxycarbonyloxy group, C2-C7 haloalkoxycarbonyloxy group, arylcarbonyl Amino group, amino group, carbamoyl group, cyano group, hydroxy group, pentafluorosulfanyl group, C1-C6 alkylamino group, C1-C6 haloalkylamino group, C2-C6 alkeni Amino group, C2-C6 haloalkenylamino group, C2-C6 alkynylamino group, C2-C6 haloalkynylamino group, C3-C9 cycloalkylamino group, C3-C9 halocycloalkylamino group, C2-C7 alkylaminocarbonyl group C2-C7 haloalkylaminocarbonyl group, C3-C7 alkenylaminocarbonyl group, C3-C7 haloalkenylaminocarbonyl group, C3-C7 alkynylaminocarbonyl group, C3-C7 haloalkynylaminocarbonyl group, C4-C10 cycloalkylaminocarbonyl A group, a C4-C10 halocycloalkylaminocarbonyl group, a phenyl group, or a heterocyclic group, and when there are a plurality of X, each X may be the same or different from each other, Y ₁ is a halogen atom, C 1 -C6 halo It indicates alkoxy group or C1-C3 haloalkyl group, _{Y 5} is plant seeds for insect damage control composition according to the a C1-C6 haloalkoxy group or a C1-C3 haloalkyl group <2>.
<13> The plant seed insect control composition according to <12>, wherein Y ₃ is a C2-C4 perfluoroalkyl group in the general formula (7).
In <14> Formula (7), _{Y 1} is a halogen atom or a C1-C3 haloalkyl group, _{Y 5} is plant seeds for insect damage control composition according to the a C1-C3 haloalkyl group <13>.
<15> The insect control composition for plant seeds according to <14>, wherein Y ₂ and Y ₄ in the general formula (7) are hydrogen atoms.

<16> The plant seed insect control composition according to <15>, wherein in the general formula (7), four X's are each independently a hydrogen atom, a halogen atom, or a cyano group.
<17> The amide derivative represented by the general formula (1) is represented by the following general formula (9):

{In General Formula (9), n is 4, X, Y _{1 to} Y ₅ , Q ₂ , G _{1 to} G ₃ , R ₁ , and R ₂ are X, Y ₁ to R in General Formula (1) Y ₅ , Q ₂ , G _{1 to} G ₃ , R ₁ , and R ₂ have the same meanings. } Insect damage control composition for plant seeds as described in said <1> represented by these.
<18> In the general formula (9), _{Y 1} is a halogen atom, a C1-C6 haloalkoxy group or a C1-C3 haloalkyl group, _{Y 5} is a C1-C6 haloalkoxy group or a C1-C3 haloalkyl group The insect control composition for plant seeds according to <17>.

<19> The plant seed insect control composition according to <18>, wherein in the general formula (9), Y ₃ is a C2-C4 perfluoroalkyl group.
<20> In the general formula (9), Y ₁ and Y ₅ are a halogen atom or a C1-C3 haloalkyl group, and either Y ₁ or Y ₅ is a C1-C3 haloalkyl group <19 > Insect damage control composition for plant seeds.
<21> The insect control composition for plant seeds according to <20>, wherein Y ₂ and Y ₄ in the general formula (9) are hydrogen atoms.
<22> The plant seed insect control composition according to <21>, wherein in the general formula (9), four X's are each independently a hydrogen atom, a halogen atom, or a cyano group.

<23> In the general formula (1), K is pyridine, pyridine-N-oxide, pyrimidine, pyrazine, pyridazine, triazine, pyrrole, pyrazole, imidazole, oxazole together with two carbon atoms to which A and A are bonded. Insect damage for plant seeds according to the above <1>, which is a non-metallic atomic group necessary for forming a cyclic linking group derived from isoxazole, thiazole, isothiazole, furan, thiophene, oxadiazole, thiodiazole or triazole Control composition.
<24> In the general formula (1), K is a group of non-metallic atoms necessary for forming a cyclic linking group derived from pyridine together with two carbon atoms to which A and A are bonded, and T Is -C (= G ₁ ) -Q ₁ , Y ₁ and Y ₅ are each independently a halogen atom or a C1-C3 haloalkyl group, as described in <23> above.

<25> In the general formula (1), K is, together with the two carbon atoms to which A and A are bonded, pyrrole, pyrazole, imidazole, oxazole, isoxazole, thiazole, isothiazole, furan, thiophene, and oxadiazole. , A non-metallic atom group necessary for forming a cyclic linking group derived from thiodiazole or triazole, and when T is —C (═G ₁ ) —Q ₁ , R ₁ is an oxygen atom, a halogen atom , Hydroxy group, nitro group, nitroso group, trimethylsilyl group, t-butyldimethylsilyl group, cyano group, amino group, optionally having C1-C6 alkyl group, optionally having substituent C1-C6 haloalkyl group, C2-C7 alkylcarbonyl group, C2-C7 haloalkylcarbonyl group, having a substituent C2-C6 alkenyl group which may have a substituent, C2-C6 haloalkenyl group which may have a substituent, C2-C6 alkynyl group which may have a substituent, C2- which may have a substituent C6-haloalkynyl group, C2-C7 alkoxycarbonyl group, C2-C7 haloalkoxycarbonyl group, C3-C7 alkenyloxycarbonyl group, C3-C7 haloalkenyloxycarbonyl group, C3-C7 alkynyloxycarbonyl group, C3-C7 haloalkynyl Oxycarbonyl group, phenoxycarbonyl group, C2-C7 alkylaminocarbonyl group, C2-C7 haloalkylaminocarbonyl group, C2-C7 alkylcarbonyloxy group, C2-C7 haloalkylcarbonyloxy group, benzoyl group, C1-C6 alkoxy group, C1 -C6 haloalkoxy Si group, C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, benzenesulfonyl group, benzylsulfonyl Group, benzyl group, or —C (═O) C (═O) R ₇ (wherein R ₇ is a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group or a C1-C6 haloalkoxy group). Group). ) The insect control composition for plant seeds according to <23>.

<26> In the general formula (1), K is, together with the two carbon atoms to which A and A are bonded, pyrrole, pyrazole, imidazole, oxazole, isoxazole, thiazole, isothiazole, furan, thiophene, and oxadiazole. , A non-metallic atom group necessary for forming a cyclic linking group derived from thiodiazole or triazole, and when T is —C (═G ₁ ) —Q ₁ , R ₂ is an oxygen atom, a halogen atom , Hydroxy group, nitro group, nitroso group, trimethylsilyl group, t-butyldimethylsilyl group, cyano group, amino group, optionally having C1-C6 alkyl group, optionally having substituent C1-C6 haloalkyl group, C2-C7 alkylcarbonyl group, C2-C7 haloalkylcarbonyl group, having a substituent C2-C6 alkenyl group which may have a substituent, C2-C6 haloalkenyl group which may have a substituent, C2-C6 alkynyl group which may have a substituent, C2- which may have a substituent C6-haloalkynyl group, C2-C7 alkoxycarbonyl group, C2-C7 haloalkoxycarbonyl group, C3-C7 alkenyloxycarbonyl group, C3-C7 haloalkenyloxycarbonyl group, C3-C7 alkynyloxycarbonyl group, C3-C7 haloalkynyl Oxycarbonyl group, phenoxycarbonyl group, C2-C7 alkylaminocarbonyl group, C2-C7 haloalkylaminocarbonyl group, C2-C7 alkylcarbonyloxy group, C2-C7 haloalkylcarbonyloxy group, benzoyl group, C1-C6 alkoxy group, C1 -C6 haloalkoxy Si group, C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, benzenesulfonyl group, benzylsulfonyl Group, benzyl group, or —C (═O) C (═O) R ₇ (wherein R ₇ is a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group or a C1-C6 haloalkoxy group). Group). ) The insect control composition for plant seeds according to <23>.

<27> The insect control composition for plant seeds according to any one of <23> to <26>, wherein Y ₃ is a C2-C4 perfluoroalkyl group in the general formula (1).
<28> In the general formula (1), Y ₁ and Y ₅ are each independently a halogen atom or a C1-C3 haloalkyl group, and one of Y ₁ and Y ₅ is a C1-C3 haloalkyl group. The insect control composition for plant seeds according to <27>.
<29> The plant seed insect control composition according to <28>, wherein in the general formula (1), Y ₂ and Y ₄ are hydrogen atoms.
<30> In the general formula (1), K represents a cyclic linking group derived from pyridine, pyridine-N-oxide, pyrrole, thiazole, furan, or thiophene together with two carbon atoms to which A and A are bonded. The insect control composition for plant seeds according to the above <29>, which is a non-metallic atomic group necessary for formation.
<31> In the general formula (1), K is necessary for forming a cyclic linking group derived from pyridine, pyridine-N-oxide, or thiazole together with two carbon atoms to which A and A are bonded. The insect control composition for plant seeds according to the above <29>, which is a nonmetallic atom group.

<32> The insect control composition for plant seeds according to <16>, wherein G ₁ and G ₃ in the general formula (7) are oxygen atoms.
<33> The insect control composition for plant seeds according to <22>, wherein in the general formula (9), G ₁ , G ₂ and G ₃ are oxygen atoms.
<34> The insect control composition for plant seeds according to <31>, wherein in the general formula (1), G ₁ , G ₂ and G ₃ are oxygen atoms.

<35> A method for preventing insect damage, comprising applying the composition according to any one of <1> to <34> to a plant seed.
<36> The method for preventing insect damage according to <35>, wherein the method applied to the plant seed is spraying treatment, smearing treatment, dipping treatment, or powdering treatment on the seed.
<37> The plant seed is corn, soybean, cotton, rice, sugar beet, wheat, barley, sunflower, tomato, cucumber, eggplant, spinach, sweet pea, pumpkin, sugar cane, tobacco, pepper, and oilseed rape seed, taro <35> The method for preventing insect damage according to <35>, selected from potato, sweet potato and konjac seeds, edible lily and tulip bulb.

<38> Plant seed to which the insect control composition for plant seed according to any one of <1> to <34> is applied.

  ADVANTAGE OF THE INVENTION According to this invention, the insect-controlling composition for plant seeds which can be applied to a plant seed and can prevent various insect damage effectively, and the prevention method of insect damage can be provided.

The insect control composition for plant seeds of the present invention contains at least one amide derivative represented by the following general formula (1).
With such a configuration, when applied to plant seeds, it has a high insecticidal control effect and can effectively suppress the occurrence of insecticidal damage.

  In general formula (1), A represents a carbon atom, an oxygen atom, a nitrogen atom, an oxidized nitrogen atom, or a sulfur atom. K together with the two carbon atoms to which A and A are attached, benzene, pyridine, pyridine-N-oxide, pyrimidine, pyrazine, pyridazine, triazine, pyrrole, pyrazole, imidazole, oxazole, isoxazole, thiazole, isothiazole, A group of nonmetallic atoms necessary for forming a cyclic linking group derived from furan, thiophene, oxadiazole, thiodiazole or triazole is shown.

  X is a hydrogen atom, halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C9 cycloalkyl group, C3-C9 halocycloalkyl group, C2-C6 alkenyl group, C2-C6 haloalkenyl group, C2- C6 alkynyl group, C2-C6 haloalkynyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, C1-C6 alkylsulfonyloxy group, C1-C6 haloalkylsulfonyloxy group, C2-C7 alkylcarbonyl group, C2-C7 haloalkylcarbonyl group, C2-C7 alkylcarbonyl Oh Si group, C2-C7 haloalkylcarbonyloxy group, arylcarbonyloxy group, C2-C7 alkoxycarbonyl group, C2-C7 haloalkoxycarbonyl group, C2-C7 alkylcarbonylamino group, C2-C7 haloalkylcarbonylamino group, C2-C7 Alkoxycarbonylamino group, C2-C7 haloalkoxycarbonylamino group, C2-C7 alkoxycarbonyloxy group, C2-C7 haloalkoxycarbonyloxy group, arylcarbonylamino group, amino group, carbamoyl group, cyano group, hydroxy group, pentafluoro Sulfanyl group, C1-C6 alkylamino group, C1-C6 haloalkylamino group, C2-C6 alkenylamino group, C2-C6 haloalkenylamino group, C2-C6 alkynylamino group, C2- 6 haloalkynylamino group, C3-C9 cycloalkylamino group, C3-C9 halocycloalkylamino group, C2-C7 alkylaminocarbonyl group, C2-C7 haloalkylaminocarbonyl group, C3-C7 alkenylaminocarbonyl group, C3-C7 Haloalkenylaminocarbonyl group, C3-C7 alkynylaminocarbonyl group, C3-C7 haloalkynylaminocarbonyl group, C4-C10 cycloalkylaminocarbonyl group, C4-C10 halocycloalkylaminocarbonyl group, phenyl group, or heterocyclic group When there are a plurality of X, each X may be the same as or different from each other.

n shows the integer of 0-4. T represents a -C ₍₌ G ₁₎ -Q 1 or _{-C (= G 1) -G 2} Q 2,. G ₁ and G ₂ each independently represent an oxygen atom or a sulfur atom, and Q ₁ and Q ₂ are a hydrogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C2-C6 alkenyl group, a C2-C6 haloalkenyl group. Group, C2-C6 alkynyl group, C2-C6 haloalkynyl group, C3-C9 cycloalkyl group, C3-C9 halocycloalkyl group, benzyl group, optionally substituted phenyl group, naphthyl group, or The heterocyclic group which may have a substituent is shown.
Y ₁ and Y ₅ each independently represent a halogen atom, a C1-C6 haloalkoxy group, or a C1-C3 haloalkyl group, and Y ₂ and Y ₄ each independently represent a hydrogen atom, a halogen atom, or a C1-C4 alkyl And Y ₃ represents a C2-C5 haloalkyl group.

In Q ₁ and Q ₂ , the optionally substituted phenyl group and optionally substituted heterocyclic group have a halogen atom, a C1-C6 alkyl group, a C1-C6 Haloalkyl group, C3-C9 cycloalkyl group, C3-C9 halocycloalkyl group, C2-C6 alkenyl group, C2-C6 haloalkenyl group, C2-C6 alkynyl group, C2-C6 haloalkynyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, C2- C7 alkylcarbonyl group, C2-C7 haloalkylcarbonyl group, C2-C7 Alkylcarbonyloxy group, C2-C7 haloalkylcarbonyloxy group, C1-C6 alkylsulfonyloxy group, C1-C6 haloalkylsulfonyloxy group, C2-C7 alkoxycarbonyl group, C2-C7 haloalkoxycarbonyl group, C2-C7 alkylcarbonylamino Group, C2-C7 haloalkylcarbonylamino group, C2-C7 alkoxycarbonylamino group, C2-C7 haloalkoxycarbonylamino group, C1-C6 alkylamino group, C1-C6 haloalkylamino group, C2-C6 alkenylamino group, C2- C6-haloalkenylamino group, C2-C6 alkynylamino group, C2-C6 haloalkynylamino group, C3-C9 cycloalkylamino group, C3-C9 halocycloalkylamino group, C2-C7 alkylamino group Nocarbonyl group, C2-C7 haloalkylaminocarbonyl group, C3-C7 alkenylaminocarbonyl group, C3-C7 haloalkenylaminocarbonyl group, C3-C7 alkynylaminocarbonyl group, C3-C7 haloalkynylaminocarbonyl group, C4-C10 cyclo Alkylaminocarbonyl group, C4-C10 halocycloalkylaminocarbonyl group, amino group, carbamoyl group, cyano group, nitro group, hydroxy group, pentafluorosulfanyl group, optionally substituted phenyl group, and substituent 1 or more substituents selected from a heterocyclic group which may have a substituent, and when there are 2 or more substituents, each substituent may be the same or different.

Further, the heterocyclic group in X, Q ₁ and Q ₂ is a pyridyl group, a pyridine-N-oxide group, a pyrimidinyl group, a pyrazinyl group, a pyridazyl group, a furyl group, a thienyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, A thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a pyrrolyl group, an imidazolyl group, a triazolyl group, a pyrazolyl group, or a tetrazolyl group;
G ₃ represents an oxygen atom or a sulfur atom.
R ₁ and R ₂ each independently have a hydrogen atom, oxygen atom, halogen atom, hydroxy group, nitro group, nitroso group, trimethylsilyl group, t-butyldimethylsilyl group, cyano group, amino group, or substituent. An optionally substituted C1-C6 alkyl group, an optionally substituted C1-C6 haloalkyl group, a C2-C7 alkylcarbonyl group, a C2-C7 haloalkylcarbonyl group, an optionally substituted C2-C6 An alkenyl group, an optionally substituted C2-C6 haloalkenyl group, an optionally substituted C2-C6 alkynyl group, an optionally substituted C2-C6 haloalkynyl group, C2-C7 alkoxycarbonyl group, C2-C7 haloalkoxycarbonyl group, C3-C7 alkenyloxycarbonyl group, C3-C7 haloal group Nyloxycarbonyl group, C3-C7 alkynyloxycarbonyl group, C3-C7 haloalkynyloxycarbonyl group, phenoxycarbonyl group, C2-C7 alkylaminocarbonyl group, C2-C7 haloalkylaminocarbonyl group, C2-C7 alkylcarbonyloxy group, C2-C7 haloalkylcarbonyloxy group, benzoyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group , C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, a benzenesulfonyl group, benzylsulfonyl group, a benzyl group or,, -C (= O) C (= O) R 7 ( wherein, _{R 7} is C1- A C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group or a C1-C6 haloalkoxy group).

However, the case where the amide derivative represented by the general formula (1) is any one of the following (A) to (I) is excluded.
(A) In the general formula (1), K is a group of nonmetallic atoms necessary for forming a cyclic linking group derived from pyridine together with two carbon atoms to which A and A are bonded, ₁ is a halogen atom, _{Y 5} is C1-C6 haloalkoxy group, when T is _{-C (= G 1) -Q 1} .
(B) In the above general formula (1), K is pyrrole, pyrazole, imidazole, oxazole, isoxazole, thiazole, isothiazole, furan, thiophene, oxadiazole together with the two carbon atoms to which A and A are bonded. , A non-metallic atom group necessary for forming a cyclic linking group derived from thiodiazole or triazole, wherein Y ₁ and Y ₅ are each independently a halogen atom, and T is —C (═G ₁ ) — When G ₂ Q ₂ .
(C) In the above general formula (1), K is pyrrole, pyrazole, imidazole, oxazole, isoxazole, thiazole, isothiazole, furan, thiophene, oxadiazole together with the two carbon atoms to which A and A are bonded. , A non-metallic atom group necessary for forming a cyclic linking group derived from thiodiazole or triazole, wherein T is —C (═G ₁ ) —Q ₁ , Y ₁ is a halogen atom, and Y ₅ Is a halogen atom or a haloalkoxy group.
(D) When it is an amide derivative represented by the following general formula (2).

In General Formula (2), Y _{2 to} Y ₄ , Q ₁ , G ₁ , G ₃ , R ₁ , and R ₂ are Y _{2 to} Y ₄ , Q ₁ , G ₁ , G ₃ in General Formula (1). , R ₁ , and R ₂ are the same as each other, Y ₁ is a halogen atom, and Y ₅ is a C1-C2 haloalkoxy group.
(E) In the general formula (2), Y ₁ and Y ₅ are halogen atoms, and Y ₃ is a C2-C3 haloalkyl group.
(F) When it is an amide derivative represented by the following general formula (3).

In General Formula (3), Y ₁ and Y ₅ are each independently a halogen atom, X ₁ and X ₃ are each independently a hydrogen atom or a fluorine atom, and Q ₁ is in General Formula (1) a synonymous with Q _{1, R 1} is a hydrogen atom or a methyl group, _{Y 3} is a C3-C4 perfluoroalkyl group.
(G) When it is an amide derivative represented by the following general formula (4).

In the general formula (4), X ₁ is a fluorine atom, X ₂ , X ₃ , and X ₄ are hydrogen atoms, Y ₁ and Y ₅ are different from each other, and are a bromine atom or a trifluoromethoxy group, ₂ and Y ₄ are a hydrogen atom, Y ₃ is a heptafluoroisopropyl group, Q ₁ is a phenyl group or a 2-chloropyridin-3-yl group, R ₁ and R ₂ are different from each other, An atom or a methyl group.
Alternatively, X ₁ is a fluorine atom, X ₂ , X ₃ , and X ₄ are hydrogen atoms, Y ₁ and Y ₅ are bromine atoms, Y ₂ and Y ₄ are hydrogen atoms, and Y ₃ is pentafluoro An ethyl group, Q ₁ is a 2-fluorophenyl group, and R ₁ and R ₂ are each independently a hydrogen atom or a methyl group;
(H) When it is an amide derivative represented by the following general formula (5).

In General Formula (5), Y ₁ and Y ₅ are each independently a halogen atom, X ₁ is a hydrogen atom or a fluorine atom, Q ₂ is a 2,2,2-trichloroethyl group, a 3,3-trifluoro -n- propyl group, _{Y 3} is a C2-C4 haloalkyl group.
(I) When it is an amide derivative represented by the following general formula (6).



In General Formula (6), Y ₁ and Y ₅ are each independently a halogen atom, Q ₂ is synonymous with Q ₂ in General Formula (1), and R ₁ is a hydrogen atom or a methyl group. , Y ₃ is a C3-C4 haloalkyl group.

  The amide derivative according to the present invention is preferably an amide derivative represented by the following general formula (7), more preferably an amide derivative represented by the following general formula (8), from the viewpoint of controlling insect damage. preferable.

In General Formula (7), X and n are 4, and Y _{1 to} Y ₅ , Q ₁ , G ₁ , G ₃ , R ₁ , and R ₂ are X, Y _{1 to} Y in General Formula (1). ₅ , Q ₁ , G ₁ , G ₃ , R ₁ , and R ₂ are synonymous with each other.

In General Formula (8), Q ₁ represents a phenyl group which may have a substituent or a pyridyl group which may have a substituent. X ₁ , X ₂ , X ₃ , and X ₄ each independently represent a hydrogen atom or a fluorine atom. R ₁ and R ₂ each independently represent a hydrogen atom or a C1-C3 alkyl group.
Y ₁ and Y ₅ each independently represent a halogen atom, a C1-C3 haloalkoxy group or a C1-C3 haloalkyl group, and Y ₂ and Y ₄ each independently represent a hydrogen atom, a halogen atom or a C1-C4 alkyl group. shows, _{Y 3} represents a C3-C4 haloalkyl group.
However, when Y ₁ and Y ₅ are simultaneously halogen atoms, at least one of X ₁ and X ₂ is a fluorine atom. When Y ₁ or Y ₅ is a C1-C3 haloalkoxy group, X ₂ is a fluorine atom.

Words used in general formulas such as the general formula (1) according to the present invention have the meanings described below in their definitions.
“Halogen atom” refers to a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.
"Ca-Cb (a, b represents an integer of 1 or more)", for example, "C1-C3" means 1 to 3 carbon atoms, and "C2-C6" Means having 2 to 6 carbon atoms, and "C1-C4" means having 1 to 4 carbon atoms.
“N-” means normal, “i-” means iso, “s-” means secondary, and “t-” means tertiary.

The “C1-C3 alkyl group” in the present invention represents a linear or branched alkyl group having 1 to 3 carbon atoms such as methyl, ethyl, n-propyl, i-propyl and the like.
Examples of the “C1-C3 haloalkyl group” include trifluoromethyl, pentafluoroethyl, heptafluoro-n-propyl, heptafluoro-i-propyl, 2,2-difluoroethyl, 2,2-dichloroethyl, 2,2 , 2-trifluoroethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2,2-trichloroethyl, 2,2,2-tribromoethyl, 1,3-difluoro-2 -Propyl, 1,3-dichloro-2-propyl, 1-chloro-3-fluoro-2-propyl, 1,1,1-trifluoro-2-propyl, 2,3,3,3-trifluoro-n -Propyl, 1,1,1,3,3,3-hexafluoro-2-propyl, 1,1,1,3,3,3-hexafluoro-2-chloro-2-propyl 1,1,1,3,3,3-hexafluoro-2-bromo-2-propyl, 1,1,2,3,3,3-hexafluoro-2-chloro-n-propyl, 1,1, 2,3,3,3-hexafluoro-2-bromo-n-propyl, 1,1,2,3,3,3-hexafluoro-1-bromo-2-propyl, 2,2,3,3 Substituted by one or more halogen atoms, which may be the same or different, such as 3-pentafluoro-n-propyl, 3-fluoro-n-propyl, 3-chloro-n-propyl, 3-bromo-n-propyl, etc. A linear or branched alkyl group having 1 to 3 carbon atoms is shown.

The “C1-C4 alkyl group” is, for example, a linear or branched carbon atom number of 1 to 4 such as methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, t-butyl and the like. An alkyl group is shown.
Examples of the “C1-C3 haloalkoxy group” include trifluoromethoxy, pentafluoroethoxy, heptafluoro-n-propyloxy, heptafluoro-i-propyloxy, 2,2-difluoroethoxy, 2,2-dichloroethoxy, 2,2,2-trifluoroethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2,2-trichloroethoxy, 2,2,2-tribromoethoxy, 1 , 3-Difluoro-2-propyloxy, 1,3-dichloro-2-propyloxy, 1-chloro-3-fluoro-2-propyloxy, 1,1,1-trifluoro-2-propyloxy, 2, 3,3,3-trifluoro-n-propyloxy, 1,1,1,3,3,3-hexafluoro-2-propyl Xy, 1,1,1,3,3,3-hexafluoro-2-chloro-2-propyloxy, 1,1,1,3,3,3-hexafluoro-2-bromo-2-propyloxy, 1,1,2,3,3,3-hexafluoro-2-chloro-n-propyloxy, 1,1,2,3,3,3-hexafluoro-2-bromo-n-propyloxy, 1, 1,2,3,3,3-hexafluoro-1-bromo-2-propyloxy, 2,2,3,3,3-pentafluoro-n-propyloxy, 3-fluoro-n-propyloxy, 3 1 to 3 linear or branched carbon atoms substituted by one or more halogen atoms which may be the same or different, such as -chloro-n-propyloxy, 3-bromo-n-propyloxy, etc. An alkoxy group is shown.

“C3-C4 perfluoroalkyl group” means perfluoro-n-propyl, perfluoro-i-propyl, perfluoro-n-butyl, perfluoro-i-butyl, perfluoro-s-butyl, perfluoro- A linear or branched alkyl group having 3 to 4 carbon atoms in which all hydrogen atoms such as t-butyl are substituted with fluorine atoms.
The “C1 haloalkyl group” refers to a methyl group substituted by one or more halogen atoms, which may be the same or different, such as trifluoromethyl, 1,1-difluoro-1-bromomethyl.

  “C1-C6 alkyl group” means, for example, methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, t-butyl, n-pentyl, 2-pentyl, neopentyl, 4-methyl-2 -A linear or branched alkyl group having 1 to 6 carbon atoms, such as -pentyl, n-hexyl, 3-methyl-n-pentyl and the like.

  Examples of the “C1-C6 haloalkyl group” include trifluoromethyl, pentafluoroethyl, heptafluoro-n-propyl, heptafluoro-i-propyl, 2,2-difluoroethyl, 2,2-dichloroethyl, 2,2 , 2-trifluoroethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2,2-trichloroethyl, 2,2,2-tribromoethyl, 1,3-difluoro-2 -Propyl, 1,3-dichloro-2-propyl, 1-chloro-3-fluoro-2-propyl, 1,1,1-trifluoro-2-propyl, 2,3,3,3-trifluoro-n -Propyl, 4,4,4-trifluoro-n-butyl, 1,1,1,3,3,3-hexafluoro-2-propyl, 1,1,1,3,3,3-he Safluoro-2-chloro-2-propyl, 1,1,1,3,3,3-hexafluoro-2-bromo-2-propyl, 1,1,2,3,3,3-hexafluoro-2- Chloro-n-propyl, 1,1,2,3,3,3-hexafluoro-2-bromo-n-propyl, 1,1,2,3,3,3-hexafluoro-1-bromo-2- Propyl, 2,2,3,3,3-pentafluoro-n-propyl, 3-fluoro-n-propyl, 3-chloro-n-propyl, 3-bromo-n-propyl, 3,3,4,4 , 4-pentafluoro-2-butyl, nonafluoro-n-butyl, nonafluoro-2-butyl, 5,5,5-trifluoro-n-pentyl, 4,4,5,5,5-pentafluoro-2- Pentyl, 3-chloro-n-pentyl, 4-bromo-2- The same or different and have been linear or branched C 1 -C 6 alkyl group substituted by may also be one or more halogen atoms, such as pentyl.

“C3-C9 cycloalkyl group” means, for example, a cyclic structure such as cyclopropyl, cyclobutyl, cyclopentyl, 2-methylcyclopentyl, 3-methylcyclopentyl, cyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl and the like. And a cycloalkyl group having 3 to 9 carbon atoms.
“C3-C9 halocycloalkyl group” means, for example, one or more halogen atoms which may be the same or different, such as 2,2,3,3-tetrafluorocyclobutyl, 2-chlorocyclohexyl, 4-chlorocyclohexyl and the like. A cycloalkyl group having 3 to 9 carbon atoms having a substituted cyclic structure is shown.

The “C2-C6 alkenyl group” refers to an alkenyl group having 2 to 6 carbon atoms having a double bond in a carbon chain such as vinyl, allyl, 2-butenyl, and 3-butenyl.
Examples of the “C2-C6 haloalkenyl group” include 3,3-difluoro-2-propenyl, 3,3-dichloro-2-propenyl, 3,3-dibromo-2-propenyl, 2,3-dibromo-2- Double bonds in carbon chains substituted by one or more halogen atoms, which may be the same or different, such as propenyl, 4,4-difluoro-3-butenyl, 3,4,4-tribromo-3-butenyl, etc. And a linear or branched alkenyl group having 2 to 6 carbon atoms.

The “C2-C6 alkynyl group” means, for example, 2 to 6 carbon atoms having a triple bond in a carbon chain such as propargyl, 1-butyn-3-yl, 1-butyn-3-methyl-3-yl, etc. Represents an alkynyl group.
"C2-C6 haloalkynyl group" means, for example, fluoroethynyl, chloroethynyl, bromoethynyl, 3,3,3-trifluoro-1-propynyl, 3,3,3-trichloro-1-propynyl, 3,3, Same or different such as 3-tribromo-1-propynyl, 4,4,4-trifluoro-1-butynyl, 4,4,4-trichloro-1-butynyl, 4,4,4-tribromo-1-butynyl A linear or branched alkynyl group having 2 to 6 carbon atoms having a triple bond in a carbon chain substituted by one or more halogen atoms may be represented.

Examples of the “C1-C6 alkoxy group” include methoxy, ethoxy, n-propyloxy, i-propyloxy, cyclopropoxy, n-butoxy, s-butoxy, i-butoxy, t-butoxy, n-pentyloxy, i -A linear, branched or cyclic alkoxy group having 1 to 6 carbon atoms such as pentyloxy, n-hexyloxy and cyclohexyloxy.
Examples of the “C1-C6 haloalkoxy group” include trifluoromethoxy, pentafluoroethoxy, 2-chloroethoxy, 2,2,2-trifluoroethoxy, heptafluoro-n-propoxy, heptafluoro-i-propoxy, 1 , 1,1,3,3,3-hexafluoro-2-propoxy, 3-fluoro-n-propoxy, 1-chlorocyclopropoxy, 2-bromocyclopropoxy, 3,3,4,4,4-pentafluoro 2-butoxy, nonafluoro-n-butoxy, nonafluoro-2-butoxy, 5,5,5-trifluoro-n-pentyloxy, 4,4,5,5,5-pentafluoro-2-pentyloxy, 3 -Chloro-n-pentyloxy, 4-bromo-2-pentyloxy, 4-chlorobutyloxy, 2-iodo-n-propi The same or different substituted by one or more halogen atoms may be linear or branched or cyclic C 1 -C 6 alkoxy group such as oxy.

Examples of the “C1-C6 alkylthio group” include methylthio, ethylthio, n-propylthio, i-propylthio, cyclopropylthio, n-butylthio, s-butylthio, i-butylthio, t-butylthio, n-pentylthio, i-pentylthio. , N-hexylthio, cyclohexylthio and the like, a linear, branched or cyclic alkylthio group having 1 to 6 carbon atoms.
Examples of the “C1-C6 haloalkylthio group” include trifluoromethylthio, pentafluoroethylthio, 2-chloroethylthio, 2,2,2-trifluoroethylthio, heptafluoro-n-propylthio, heptafluoro-i-. Propylthio, 1,1,1,3,3,3-hexafluoro-2-propylthio, 3-fluoro-n-propylthio, 1-chlorocyclopropylthio, 2-bromocyclopropylthio, 3,3,4,4 , 4-pentafluoro-2-butylthio, nonafluoro-n-butylthio, nonafluoro-2-butylthio, 5,5,5-trifluoro-n-pentylthio, 4,4,5,5,5-pentafluoro-2- Pentylthio, 3-chloro-n-pentylthio, 4-bromo-2-pentylthio, 4-chlorobutylthio, 2- Shows the over de -n- same or different 1 may be more than one linear or branched or cyclic C 1 -C 6 alkylthio group substituted by a halogen atom such as propylthio.

“C1-C6 alkylsulfinyl group” means, for example, methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, i-propylsulfinyl, cyclopropylsulfinyl, n-butylsulfinyl, s-butylsulfinyl, i-butylsulfinyl, t-butyl A linear, branched or cyclic alkylsulfinyl group having 1 to 6 carbon atoms such as sulfinyl, n-pentylsulfinyl, i-pentylsulfinyl, n-hexylsulfinyl, cyclohexylsulfinyl and the like is shown.
Examples of the “C1-C6 haloalkylsulfinyl group” include trifluoromethylsulfinyl, pentafluoroethylsulfinyl, 2-chloroethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, heptafluoro-n-propylsulfinyl, heptafluoro- i-propylsulfinyl, 1,1,1,3,3,3-hexafluoro-2-propylsulfinyl, 3-fluoro-n-propylsulfinyl, 1-chlorocyclopropylsulfinyl, 2-bromocyclopropylsulfinyl, 3, 3,4,4,4-pentafluoro-2-butylsulfinyl, nonafluoro-n-butylsulfinyl, nonafluoro-2-butylsulfinyl, 5,5,5-trifluoro-n-pentylsulfinyl, 4,4,5, 5,5- One which may be the same or different, such as ntafluoro-2-pentylsulfinyl, 3-chloro-n-pentylsulfinyl, 4-bromo-2-pentylsulfinyl, 4-chlorobutylsulfinyl, 2-iodo-n-propylsulfinyl A linear, branched or cyclic alkylsulfinyl group having 1 to 6 carbon atoms substituted by the above halogen atom is shown.

Examples of the “C1-C6 alkylsulfonyl group” include methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, i-propylsulfonyl, cyclopropylsulfonyl, n-butylsulfonyl, s-butylsulfonyl, i-butylsulfonyl, t-butyl. A linear, branched or cyclic alkylsulfonyl group having 1 to 6 carbon atoms such as sulfonyl, n-pentylsulfonyl, i-pentylsulfonyl, n-hexylsulfonyl, cyclohexylsulfonyl and the like is shown.
Examples of the “C1-C6 haloalkylsulfonyl group” include trifluoromethylsulfonyl, pentafluoroethylsulfonyl, 2-chloroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, heptafluoro-n-propylsulfonyl, heptafluoro- i-propylsulfonyl, 1,1,1,3,3,3-hexafluoro-2-propylsulfonyl, 3-fluoro-n-propylsulfonyl, 1-chlorocyclopropylsulfonyl, 2-bromocyclopropylsulfonyl, 3, 3,4,4,4-pentafluoro-2-butylsulfonyl, nonafluoro-n-butylsulfonyl, nonafluoro-2-butylsulfonyl, 5,5,5-trifluoro-n-pentylsulfonyl, 4,4,5, 5,5-pentafluoro-2-pentyls By one or more halogen atoms which may be the same or different, such as phonyl, 3-chloro-n-pentylsulfonyl, 4-bromo-2-pentylsulfonyl, 4-chlorobutylsulfonyl, 2-iodo-n-propylsulfonyl, etc. A substituted linear, branched or cyclic alkylsulfonyl group having 1 to 6 carbon atoms is shown.

Examples of the “C1-C6 alkylsulfonyloxy group” include methanesulfonyloxy, ethanesulfonyloxy, n-propanesulfonyloxy, i-propanesulfonyloxy, cyclopropanesulfonyloxy, n-butanesulfonyloxy, s-butanesulfonyloxy, 1-butanesulfonyloxy, t-butanesulfonyloxy, n-pentanesulfonyloxy, i-pentanesulfonyloxy, n-hexanesulfonyloxy, cyclohexanesulfonyloxy, etc. 6 alkylsulfonyloxy groups are shown.
Examples of the “C1-C6 haloalkylsulfonyloxy group” include trifluoromethanesulfonyloxy, pentafluoropropanesulfonyloxy, 2-chloropropanesulfonyloxy, 2,2,2-trifluoropropanesulfonyloxy, heptafluoro-n-propanesulfonyloxy. , Heptafluoro-i-propanesulfonyloxy, 1,1,1,3,3,3-hexafluoro-2-propanesulfonyloxy, 3-fluoro-n-propanesulfonyloxy, 1-chlorocyclopropanesulfonyloxy, 2 -Bromocyclopropanesulfonyloxy, 3,3,4,4,4-pentafluoro-2-butanesulfonyloxy, nonafluoro-n-butanesulfonyloxy, nonafluoro-2-butanesulfonyloxy, 5,5,5 Trifluoro-n-pentanesulfonyloxy, 4,4,5,5,5-pentafluoro-2-pentanesulfonyloxy, 3-chloro-n-pentanesulfonyloxy, 4-bromo-2-pentanesulfonyloxy, 4- 1 to 6 linear, branched or cyclic carbon atoms substituted by one or more halogen atoms which may be the same or different, such as chlorobutanesulfonyloxy, 2-iodo-n-propanesulfonyloxy and the like An alkylsulfonyloxy group is shown.

Examples of the “C2-C7 alkylcarbonyl group” include acetyl, propionyl, i-propylcarbonyl, cyclopropylcarbonyl, n-butylcarbonyl, s-butylcarbonyl, t-butylcarbonyl, n-pentylcarbonyl, 2-pentylcarbonyl, A linear, branched or cyclic alkylcarbonyl group having 2 to 7 carbon atoms such as neopentylcarbonyl and cyclopentylcarbonyl is shown.
Examples of the “C2-C7 haloalkylcarbonyl group” include trifluoroacetyl, pentafluoropropionyl, 2-chloropropionyl, 2,2,2-trifluoropropionyl, heptafluoro-n-propylcarbonyl, heptafluoro-i-propylcarbonyl. 1,1,1,3,3,3-hexafluoro-2-propylcarbonyl, 3-fluoro-n-propylcarbonyl, 1-chlorocyclopropylcarbonyl, 2-bromocyclopropylcarbonyl, 3,3,4, 4,4-pentafluoro-2-butylcarbonyl, nonafluoro-n-butylcarbonyl, nonafluoro-2-butylcarbonyl, 5,5,5-trifluoro-n-pentylcarbonyl, 4,4,5,5,5- Pentafluoro-2-pentylcarbonyl, 3-chloro a straight chain substituted by one or more halogen atoms, which may be the same or different, such as n-pentylcarbonyl, 4-bromo-2-pentylcarbonyl, 4-chlorobutylcarbonyl, 2-iodo-n-propylcarbonyl, etc. Alternatively, it represents a branched or cyclic alkylcarbonyl group having 2 to 7 carbon atoms.

Examples of the “C2-C7 alkylcarbonyloxy group” include acetyloxy, propionyloxy, i-propylcarbonyloxy, cyclopropylcarbonyloxy, n-butylcarbonyloxy, s-butylcarbonyloxy, t-butylcarbonyloxy, n- A linear, branched or cyclic alkylcarbonyloxy group having 2 to 7 carbon atoms such as pentylcarbonyloxy, 2-pentylcarbonyloxy, neopentylcarbonyloxy, cyclopentylcarbonyloxy and the like is shown.
Examples of the “C2-C7 haloalkylcarbonyloxy group” include trifluoroacetyloxy, pentafluoropropionyloxy, 2-chloropropionyloxy, 2,2,2-trifluoropropionyloxy, heptafluoro-n-propylcarbonyloxy, hepta Fluoro-i-propylcarbonyloxy, 1,1,1,3,3,3-hexafluoro-2-propylcarbonyloxy, 3-fluoro-n-propylcarbonyloxy, 1-chlorocyclopropylcarbonyloxy, 2-bromo Cyclopropylcarbonyloxy, 3,3,4,4,4-pentafluoro-2-butylcarbonyloxy, nonafluoro-n-butylcarbonyloxy, nonafluoro-2-butylcarbonyloxy, 5,5,5-trifluoro-n -Pliers Carbonyloxy, 4,4,5,5,5-pentafluoro-2-pentylcarbonyloxy, 3-chloro-n-pentylcarbonyloxy, 4-bromo-2-pentylcarbonyloxy, 4-chlorobutylcarbonyloxy, 2 A linear, branched or cyclic alkylcarbonyloxy group having 2 to 7 carbon atoms substituted with one or more halogen atoms which may be the same or different, such as iodo-n-propylcarbonyloxy Show.

Examples of the “C2-C7 alkoxycarbonyl group” include methoxycarbonyl, ethoxycarbonyl, isopropoxycarbonyl, cyclopropoxycarbonyl, n-butoxycarbonyl, s-butoxycarbonyl, t-butoxycarbonyl, n-pentyloxycarbonyl, 2-pentyl. A linear, branched or cyclic alkoxycarbonyl group having 2 to 7 carbon atoms such as oxycarbonyl, neopentyloxycarbonyl, cyclopentyloxycarbonyl and the like is shown.
“C2-C7 haloalkoxycarbonyl group” means, for example, trifluoromethoxycarbonyl, pentafluoroethoxycarbonyl, 2-chloroethoxycarbonyl, 2,2,2-trifluoroethoxycarbonyl, heptafluoro-n-propoxycarbonyl, heptafluoro -I-propoxycarbonyl, 1,1,1,3,3,3-hexafluoro-2-propoxycarbonyl, 3-fluoro-n-propoxycarbonyl, 1-chlorocyclopropoxycarbonyl, 2-bromocyclopropoxycarbonyl, 3 , 3,4,4,4-pentafluoro-2-butoxycarbonyl, nonafluoro-n-butoxycarbonyl, nonafluoro-2-butoxycarbonyl, 5,5,5-trifluoro-n-pentyloxycarbonyl, 4,4, 5, 5, -Pentafluoro-2-pentyloxycarbonyl, 3-chloro-n-pentyloxycarbonyl, 4-bromo-2-pentyloxycarbonyl, 4-chlorobutyloxycarbonyl, 2-iodo-n-propyloxycarbonyl and the like or A linear, branched or cyclic alkoxycarbonyl group having 2 to 7 carbon atoms, which is substituted with one or more halogen atoms which may be different.

Examples of the “C2-C7 alkylcarbonylamino group” include acetylamino, propionylamino, n-propylcarbonylamino, i-propylcarbonylamino, cyclopropylcarbonylamino, n-butylcarbonylamino, s-butylcarbonylamino, i- 2 to 7 linear, branched or cyclic carbon atoms such as butylcarbonylamino, t-butylcarbonylamino, n-pentylcarbonylamino, i-pentylcarbonylamino, n-hexylcarbonylamino, cyclohexylcarbonylamino Represents an alkylcarbonylamino group.
Examples of the “C2-C7 haloalkylcarbonylamino group” include trifluoroacetylamino, pentafluoropropionylamino, 2-chloropropionylamino, 2,2,2-trifluoropropionylamino, heptafluoro-n-propylcarbonylamino, hepta Fluoro-i-propylcarbonylamino, 1,1,1,3,3,3-hexafluoro-2-propylcarbonylamino, 3-fluoro-n-propylcarbonylamino, 1-chlorocyclopropylcarbonylamino, 2-bromo Cyclopropylcarbonylamino, 3,3,4,4,4-pentafluoro-2-butylcarbonylamino, nonafluoro-n-butylcarbonylamino, nonafluoro-2-butylcarbonylamino, 5,5,5-trifluoro-n -Pliers Carbonylamino, 4,4,5,5,5-pentafluoro-2-pentylcarbonylamino, 3-chloro-n-pentylcarbonylamino, 4-bromo-2-pentylcarbonylamino, 4-chlorobutylcarbonylamino, 2 A linear, branched or cyclic alkylcarbonylamino group having 2 to 7 carbon atoms substituted with one or more halogen atoms which may be the same or different, such as iodo-n-propylcarbonylamino Show.

“C2-C7 alkoxycarbonylamino group” means, for example, methoxycarbonylamino, ethoxycarbonylamino, n-propyloxycarbonylamino, i-propyloxycarbonylamino, cyclopropoxycarbonylamino, n-butoxycarbonylamino, s-butoxycarbonyl Linear, branched or cyclic such as amino, i-butoxycarbonylamino, t-butoxycarbonylamino, n-pentyloxycarbonylamino, i-pentyloxycarbonylamino, n-hexyloxycarbonylamino, cyclohexyloxycarbonylamino And an alkoxycarbonylamino group having 2 to 7 carbon atoms.
Examples of the “C2-C7 haloalkoxycarbonylamino group” include trifluoromethyloxycarbonylamino, pentafluoroethoxycarbonylamino, 2-chloroethoxycarbonylamino, 2,2,2-trifluoroethoxycarbonylamino, heptafluoro-n. -Propyloxycarbonylamino, heptafluoro-i-propyloxycarbonylamino, 1,1,1,3,3,3-hexafluoro-2-propyloxycarbonylamino, 3-fluoro-n-propyloxycarbonylamino, 1 -Chlorocyclopropyloxycarbonylamino, 2-bromocyclopropyloxycarbonylamino, 3,3,4,4,4-pentafluoro-2-butyloxycarbonylamino, nonafluoro-n-butyloxycarbonylamino , Nonafluoro-2-butyloxycarbonylamino, 5,5,5-trifluoro-n-pentyloxycarbonylamino, 4,4,5,5,5-pentafluoro-2-pentyloxycarbonylamino, 3-chloro- one or more halogens which may be the same or different, such as n-pentyloxycarbonylamino, 4-bromo-2-pentyloxycarbonylamino, 4-chlorobutyloxycarbonylamino, 2-iodo-n-propyloxycarbonylamino, etc. A linear, branched or cyclic alkoxycarbonylamino group having 2 to 7 carbon atoms substituted by an atom is shown.

“C2-C7 alkoxycarbonyloxy group” means, for example, methoxycarbonyloxy, ethoxycarbonyloxy, n-propyloxycarbonyloxy, i-propyloxycarbonyloxy, cyclopropoxycarbonyloxy, n-butoxycarbonyloxy, s-butoxycarbonyl Linear, branched or cyclic such as oxy, i-butoxycarbonyloxy, t-butoxycarbonyloxy, n-pentyloxycarbonyloxy, i-pentyloxycarbonyloxy, n-hexyloxycarbonyloxy, cyclohexyloxycarbonyloxy, etc. And an alkoxycarbonyloxy group having 2 to 7 carbon atoms.
Examples of the “C2-C7 haloalkoxycarbonyloxy group” include trifluoromethyloxycarbonyloxy, pentafluoroethoxycarbonyloxy, 2-chloroethoxycarbonyloxy, 2,2,2-trifluoroethoxycarbonyloxy, heptafluoro-n. -Propyloxycarbonyloxy, heptafluoro-i-propyloxycarbonyloxy, 1,1,1,3,3,3-hexafluoro-2-propyloxycarbonyloxy, 3-fluoro-n-propyloxycarbonyloxy, 1 -Chlorocyclopropyloxycarbonyloxy, 2-bromocyclopropyloxycarbonyloxy, 3,3,4,4,4-pentafluoro-2-butyloxycarbonyloxy, nonafluoro-n-butyloxycarbonyloxy , Nonafluoro-2-butyloxycarbonyloxy, 5,5,5-trifluoro-n-pentyloxycarbonyloxy, 4,4,5,5,5-pentafluoro-2-pentyloxycarbonyloxy, 3-chloro- one or more halogens which may be the same or different, such as n-pentyloxycarbonyloxy, 4-bromo-2-pentyloxycarbonyloxy, 4-chlorobutyloxycarbonyloxy, 2-iodo-n-propyloxycarbonyloxy, etc. A linear, branched or cyclic alkoxycarbonyloxy group having 2 to 7 carbon atoms substituted by an atom is shown.

“C1-C6 alkylamino group” means, for example, methylamino, dimethylamino, ethylamino, diethylamino, n-propylamino, i-propylamino, cyclopropylamino, n-butylamino, s-butylamino, i-butyl A linear, branched or cyclic alkylamino group having 1 to 6 carbon atoms such as amino, t-butylamino, n-pentylamino, i-pentylamino, n-hexylamino, cyclohexylamino and the like is shown.
“C1-C6 haloalkylamino group” means, for example, trifluoromethylamino, ditrifluoromethylamino, pentafluoroethylamino, dipentafluoroethylamino, 2-chloroethylamino, 2,2,2-trifluoroethylamino, Heptafluoro-n-propylamino, heptafluoro-i-propylamino, 1,1,1,3,3,3-hexafluoro-2-propylamino, 3-fluoro-n-propylamino, 1-chlorocyclopropyl Amino, 2-bromocyclopropylamino, 3,3,4,4,4-pentafluoro-2-butylamino, nonafluoro-n-butylamino, nonafluoro-2-butylamino, 5,5,5-trifluoro- n-pentylamino, 4,4,5,5,5-pentafluoro-2-pentylami Substituted with one or more halogen atoms which may be the same or different, such as 3-chloro-n-pentylamino, 4-bromo-2-pentylamino, 4-chlorobutylamino, 2-iodo-n-propylamino, etc. A linear, branched or cyclic alkylamino group having 1 to 6 carbon atoms.

The “C2-C6 alkenyloxy group” refers to an alkenyloxy group having 2 to 6 carbon atoms having a double bond in a carbon chain such as vinyloxy, allyloxy, 2-butenyloxy, 3-butenyloxy and the like.
Examples of the “C2-C6 haloalkenyloxy group” include 3,3-difluoro-2-propenyloxy, 3,3-dichloro-2-propenyloxy, 3,3-dibromo-2-propenyloxy, 2,3- In a carbon chain substituted by one or more halogen atoms, which may be the same or different, such as dibromo-2-propenyloxy, 4,4-difluoro-3-butenyloxy, 3,4,4-tribromo-3-butenyloxy, etc. Represents a linear or branched alkenyloxy group having 2 to 6 carbon atoms having a double bond.

The “C2-C6 alkynyloxy group” means, for example, a carbon atom number of 2 to 3 having a triple bond in a carbon chain such as propargyloxy, 1-butyn-3-yloxy, 1-butyn-3-methyl-3-yloxy, etc. 6 alkynyloxy groups are shown.
“C2-C6 haloalkynyloxy group” means, for example, fluoroethynyloxy, chloroethynyloxy, bromoethynyloxy, 3,3,3-trifluoro-1-propynyloxy, 3,3,3-trichloro-1-propynyl Oxy, 3,3,3-tribromo-1-propynyloxy, 4,4,4-trifluoro-1-butynyloxy, 4,4,4-trichloro-1-butynyloxy, 4,4,4-tribromo-1- A linear or branched alkynyloxy group having 2 to 6 carbon atoms having a triple bond in a carbon chain substituted with one or more halogen atoms which may be the same or different, such as butynyloxy.

Examples of the “C3-C9 cycloalkoxy group” include cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, 2-methylcyclopentyloxy, 3-methylcyclopentyloxy, cyclohexyloxy, 2-methylcyclohexyloxy, 3-methylcyclohexyloxy, A cycloalkyloxy group having 3 to 9 carbon atoms having a cyclic structure such as 4-methylcyclohexyloxy is shown.
The “C3-C9 halocycloalkoxy group” is, for example, one or more which may be the same or different such as 2,2,3,3-tetrafluorocyclobutyloxy, 2-chlorocyclohexyloxy, 4-chlorocyclohexyloxy and the like A cycloalkyloxy group having 3 to 9 carbon atoms having a cyclic structure substituted by a halogen atom is shown.

The “C3-C7 alkenylcarbonyl group” is an alkenyl having 3 to 7 carbon atoms having a double bond in a carbon chain such as vinylcarbonyl, allylcarbonyl, 2-butenylcarbonyl, 3-butenylcarbonyl, etc. A carbonyl group is shown.
Examples of the “C3-C7 haloalkenylcarbonyl group” include 3,3-difluoro-2-propenylcarbonyl, 3,3-dichloro-2-propenylcarbonyl, 3,3-dibromo-2-propenylcarbonyl, 2,3- Substituted by one or more halogen atoms, which may be the same or different, such as dibromo-2-propenylcarbonyl, 4,4-difluoro-3-butenylcarbonyl, 3,4,4-tribromo-3-butenylcarbonyl, etc. A linear or branched alkenylcarbonyl group having 3 to 7 carbon atoms having a double bond in the carbon chain is shown.

The “C3-C7 alkynylcarbonyl group” means 3 carbon atoms having a triple bond in a carbon chain such as propargylcarbonyl, 1-butyn-3-ylcarbonyl, 1-butyn-3-methyl-3-ylcarbonyl, etc. -7 alkynylcarbonyl groups are shown.
“C3-C7 haloalkynylcarbonyl group” means, for example, fluoroethynylcarbonyl, chloroethynylcarbonyl, bromoethynylcarbonyl, 3,3,3-trifluoro-1-propynylcarbonyl, 3,3,3-trichloro-1-propynyl Carbonyl, 3,3,3-tribromo-1-propynylcarbonyl, 4,4,4-trifluoro-1-butynylcarbonyl, 4,4,4-trichloro-1-butynylcarbonyl, 4,4,4- 3 to 7 linear or branched carbon atoms having a triple bond in a carbon chain substituted by one or more halogen atoms, which may be the same or different, such as tribromo-1-butynylcarbonyl An alkynylcarbonyl group is shown.

“C4-C10 cycloalkylcarbonyl group” means, for example, cyclopropylcarbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl, 2-methylcyclopentylcarbonyl, 3-methylcyclopentylcarbonyl, cyclohexylcarbonyl, 2-methylcyclohexylcarbonyl, 3-methylcyclohexylcarbonyl And a cycloalkylcarbonyl group having 4 to 10 carbon atoms having a cyclic structure such as 4-methylcyclohexylcarbonyl.
The “C4-C10 halocycloalkylcarbonyl group” may be the same or different, for example, 2,2,3,3-tetrafluorocyclobutylcarbonyl, 2-chlorocyclohexylcarbonyl, 4-chlorocyclohexylcarbonyl, etc. A cycloalkylcarbonyl group having 4 to 10 carbon atoms having a cyclic structure substituted with a halogen atom.

The “C3-C7 alkenyloxycarbonyl group” means a carbon atom number 3 having a double bond in a carbon chain such as vinyloxycarbonyl, allyloxycarbonyl, 2-butenyloxycarbonyl, 3-butenyloxycarbonyl and the like. 7 alkenyloxycarbonyl groups are shown.
Examples of the “C3-C7 haloalkenyloxycarbonyl group” include 3,3-difluoro-2-propenyloxycarbonyl, 3,3-dichloro-2-propenyloxycarbonyl, 3,3-dibromo-2-propenyloxycarbonyl, One or more which may be the same or different, such as 2,3-dibromo-2-propenyloxycarbonyl, 4,4-difluoro-3-butenyloxycarbonyl, 3,4,4-tribromo-3-butenyloxycarbonyl, etc. A straight chain or branched chain alkenyloxycarbonyl group having 3 to 7 carbon atoms having a double bond in the carbon chain substituted by a halogen atom.

The “C3-C7 alkynyloxycarbonyl group” means a triple bond in a carbon chain such as propargyloxycarbonyl, 1-butyn-3-yloxycarbonyl, 1-butyn-3-methyl-3-yloxycarbonyl, etc. And an alkynyloxycarbonyl group having 3 to 7 carbon atoms.
Examples of the “C3-C7 haloalkynyloxycarbonyl group” include fluoroethynyloxycarbonyl, chloroethynyloxycarbonyl, bromoethynyloxycarbonyl, 3,3,3-trifluoro-1-propynyloxycarbonyl, 3,3,3- Trichloro-1-propynyloxycarbonyl, 3,3,3-tribromo-1-propynyloxycarbonyl, 4,4,4-trifluoro-1-butynyloxycarbonyl, 4,4,4-trichloro-1-butynyl Linear or branched having a triple bond in a carbon chain substituted by one or more halogen atoms which may be the same or different, such as oxycarbonyl, 4,4,4-tribromo-1-butynyloxycarbonyl, etc. An alkynyloxycarbonyl group having 3 to 7 carbon atoms.

“C4-C10 cycloalkyloxycarbonyl group” means, for example, cyclopropyloxycarbonyl, cyclobutyloxycarbonyl, cyclopentyloxycarbonyl, 2-methylcyclopentyloxycarbonyl, 3-methylcyclopentyloxycarbonyl, cyclohexyloxycarbonyl, 2-methylcyclohexyl A cycloalkyloxycarbonyl group having 4 to 10 carbon atoms having a cyclic structure such as oxycarbonyl, 3-methylcyclohexyloxycarbonyl, 4-methylcyclohexyloxycarbonyl and the like is shown.
The “C4-C10 halocycloalkyloxycarbonyl group” is the same as or different from, for example, 2,2,3,3-tetrafluorocyclobutyloxycarbonyl, 2-chlorocyclohexyloxycarbonyl, 4-chlorocyclohexyloxycarbonyl, etc. Or a cycloalkyloxycarbonyl group having 4 to 10 carbon atoms having a cyclic structure substituted by one or more halogen atoms.

The “C2-C6 alkenylamino group” refers to an alkenylamino group having 2 to 6 carbon atoms having a double bond in a carbon chain such as vinylamino, allylamino, 2-butenylamino, 3-butenylamino and the like.
"C2-C6 haloalkenylamino group" means 3,3-difluoro-2-propenylamino, 3,3-dichloro-2-propenylamino, 3,3-dibromo-2-propenylamino, 2,3-dibromo In a carbon chain substituted by one or more halogen atoms, which may be the same or different, such as 2-propenylamino, 4,4-difluoro-3-butenylamino, 3,4,4-tribromo-3-butenylamino, etc. A linear or branched alkenylamino group having 2 to 6 carbon atoms having a double bond is shown.

The “C2-C6 alkynylamino group” means, for example, a carbon number of 2 to 3 having a triple bond in a carbon chain such as propargylamino, 1-butyn-3-ylamino, 1-butyn-3-methyl-3-ylamino and the like. 6 alkynylamino groups are shown.
“C2-C6 haloalkynylamino group” means, for example, fluoroethynylamino, chloroethynylamino, bromoethynylamino, 3,3,3-trifluoro-1-propynylamino, 3,3,3-trichloro-1-propynyl Amino, 3,3,3-tribromo-1-propynylamino, 4,4,4-trifluoro-1-butynylamino, 4,4,4-trichloro-1-butynylamino, 4,4,4-tribromo-1- A linear or branched alkynylamino group having 2 to 6 carbon atoms having a triple bond in a carbon chain substituted by one or more halogen atoms, which may be the same or different, such as butynylamino.

“C3-C9 cycloalkylamino group” means, for example, cyclopropylamino, cyclobutylamino, cyclopentylamino, 2-methylcyclopentylamino, 3-methylcyclopentylamino, cyclohexylamino, 2-methylcyclohexylamino, 3-methylcyclohexylamino And cycloalkyl group amino having 3 to 9 carbon atoms having a cyclic structure such as 4-methylcyclohexylamino.
The “C3-C9 halocycloalkylamino group” may be the same or different, for example, 2,2,3,3-tetrafluorocyclobutylamino, 2-chlorocyclohexylamino, 4-chlorocyclohexylamino and the like. A cycloalkylamino group having 3 to 9 carbon atoms and having a cyclic structure substituted by a halogen atom.

  “C2-C7 alkylaminocarbonyl group” means, for example, methylaminocarbonyl, ethylaminocarbonyl, n-propylaminocarbonyl, i-propylaminocarbonyl, n-butylaminocarbonyl, s-butylaminocarbonyl, t-butylaminocarbonyl , N-pentylaminocarbonyl, 2-pentylaminocarbonyl, neopentylaminocarbonyl, 4-methyl-2-pentylaminocarbonyl, n-hexylaminocarbonyl, 3-methyl-n-pentylaminocarbonyl, etc. A chain-like alkylaminocarbonyl group having 2 to 7 carbon atoms is shown.

  Examples of the “C2-C7 haloalkylaminocarbonyl group” include trifluoromethylaminocarbonyl, pentafluoroethylaminocarbonyl, heptafluoro-n-propylaminocarbonyl, heptafluoro-i-propylaminocarbonyl, 2,2-difluoroethylamino. Carbonyl, 2,2-dichloroethylaminocarbonyl, 2,2,2-trifluoroethylaminocarbonyl, 2-fluoroethylaminocarbonyl, 2-chloroethylaminocarbonyl, 2-bromoethylaminocarbonyl, 2-iodoethylaminocarbonyl 2,2,2-trichloroethylaminocarbonyl, 2,2,2-tribromoethylaminocarbonyl, 1,3-difluoro-2-propylaminocarbonyl, 1,3-dichloro-2-propylamino Carbonyl, 1-chloro-3-fluoro-2-propylaminocarbonyl, 1,1,1-trifluoro-2-propylaminocarbonyl, 2,3,3,3-trifluoro-n-propylaminocarbonyl, 4, 4,4-trifluoro-n-butylaminocarbonyl, 1,1,1,3,3,3-hexafluoro-2-propylaminocarbonyl, 1,1,1,3,3,3-hexafluoro-2 -Chloro-2-propylaminocarbonyl, 1,1,1,3,3,3-hexafluoro-2-bromo-2-propylaminocarbonyl, 1,1,2,3,3,3-hexafluoro-2 -Chloro-n-propylaminocarbonyl, 1,1,2,3,3,3-hexafluoro-2-bromo-n-propylaminocarbonyl, 1,1,2,3,3,3-hex Fluoro-1-bromo-2-propylaminocarbonyl, 2,2,3,3,3-pentafluoro-n-propylaminocarbonyl, 3-fluoro-n-propylaminocarbonyl, 3-chloro-n-propylaminocarbonyl 3-bromo-n-propylaminocarbonyl, 3,3,4,4,4-pentafluoro-2-butylaminocarbonyl, nonafluoro-n-butylaminocarbonyl, nonafluoro-2-butylaminocarbonyl, 5,5, 5-trifluoro-n-pentylaminocarbonyl, 4,4,5,5,5-pentafluoro-2-pentylaminocarbonyl, 3-chloro-n-pentylaminocarbonyl, 4-bromo-2-pentylaminocarbonyl, etc. Substituted by one or more halogen atoms which may be the same or different And a linear or branched alkylaminocarbonyl group having 2 to 7 carbon atoms.

The “C3-C7 alkenylaminocarbonyl group” means, for example, a carbon atom having a double bond in a carbon chain such as vinylaminocarbonyl, allylaminocarbonyl, 2-butenylaminocarbonyl, 3-butenylaminocarbonyl, etc. Represents -7 alkenylaminocarbonyl groups.
“C3-C7 haloalkenylaminocarbonyl group” means, for example, 3,3-difluoro-2-propenylaminocarbonyl, 3,3-dichloro-2-propenylaminocarbonyl, 3,3-dibromo-2-propenylaminocarbonyl, One or more which may be the same or different, such as 2,3-dibromo-2-propenylaminocarbonyl, 4,4-difluoro-3-butenylaminocarbonyl, 3,4,4-tribromo-3-butenylaminocarbonyl, etc. A linear or branched alkenylaminocarbonyl group having 3 to 7 carbon atoms having a double bond in the carbon chain substituted with a halogen atom.

“C3-C7 alkynylaminocarbonyl group” means, for example, a triple bond in a carbon chain such as propargylaminocarbonyl, 1-butyn-3-ylaminocarbonyl, 1-butyn-3-methyl-3-ylaminocarbonyl, etc. And an alkynylaminocarbonyl group having 3 to 7 carbon atoms.
Examples of the “C3-C7 haloalkynylaminocarbonyl group” include fluoroethynylaminocarbonyl, chloroethynylaminocarbonyl, bromoethynylaminocarbonyl, 3,3,3-trifluoro-1-propynylaminocarbonyl, 3,3,3- Trichloro-1-propynylaminocarbonyl, 3,3,3-tribromo-1-propynylaminocarbonyl, 4,4,4-trifluoro-1-butynylaminocarbonyl, 4,4,4-trichloro-1-butynyl Linear or branched having a triple bond in a carbon chain substituted by one or more halogen atoms which may be the same or different, such as aminocarbonyl, 4,4,4-tribromo-1-butynylaminocarbonyl, etc. An alkynylaminocarbonyl group having 3 to 7 carbon atoms.

“C4-C10 cycloalkylaminocarbonyl group” means, for example, cyclopropylaminocarbonyl, cyclobutylaminocarbonyl, cyclopentylaminocarbonyl, 2-methylcyclopentylaminocarbonyl, 3-methylcyclopentylaminocarbonyl, cyclohexylaminocarbonyl, 2-methylcyclohexyl. A cycloalkylaminocarbonyl group having 4 to 10 carbon atoms having a cyclic structure such as aminocarbonyl, 3-methylcyclohexylaminocarbonyl, 4-methylcyclohexylaminocarbonyl and the like is shown.
The “C4-C10 halocycloalkylaminocarbonyl group” may be the same as or different from, for example, 2,3,3-tetrafluorocyclobutylaminocarbonyl, 2-chlorocyclohexylaminocarbonyl, 4-chlorocyclohexylaminocarbonyl, etc. A cycloalkylaminocarbonyl group having 4 to 10 carbon atoms having a cyclic structure substituted by one or more halogen atoms is shown.

“Aryl group” refers to, for example, a monocyclic or polycyclic aromatic hydrocarbon group such as a phenyl group or a naphthyl group.
The “arylcarbonyloxy group” refers to an arylcarbonyloxy group such as a phenylcarbonyloxy group or a naphthylcarbonyloxy group.
The “arylcarbonylamino group” refers to an arylcarbonylamino group such as a phenylcarbonylamino group or a naphthylcarbonylamino group.

The “optionally substituted C1-C6 alkyl group” in R ₁ and R ₂ is an unsubstituted linear, branched or cyclic alkyl group having 1 to 6 carbon atoms, or , A linear, branched or cyclic carbon substituted with at least one of a nitro group, an optionally substituted phenyl group, and an optionally substituted unsaturated heterocyclic group An alkyl group having 1 to 6 atoms is shown. In addition, when there are two or more substituents, these substituents may be the same or different.
The “optionally substituted C1-C6 haloalkyl group” in R ₁ and R ₂ is a linear, branched or cyclic carbon atom having 1 to 1 carbon atoms substituted only by one or more halogen atoms. In addition to six alkyl groups, or one or more halogen atoms, at least one of a nitro group, an optionally substituted phenyl group, and an optionally substituted unsaturated heterocyclic group A linear, branched, or cyclic alkyl group having 1 to 6 carbon atoms substituted with is shown.

The “optionally substituted C2-C6 alkenyl group” for R ₁ and R ₂ is an unsubstituted linear, branched or cyclic alkenyl group having 2 to 6 carbon atoms, or , A linear, branched or cyclic carbon substituted with at least one of a nitro group, an optionally substituted phenyl group, and an optionally substituted unsaturated heterocyclic group An alkenyl group having 2 to 6 atoms is shown. In addition, when there are two or more substituents, these substituents may be the same or different.
The “optionally substituted C2-C6 haloalkenyl group” in R ₁ and R ₂ is a linear, branched or cyclic carbon atom number of 2 substituted only by one or more halogen atoms -6 alkenyl groups, or at least one of a nitro group, an optionally substituted phenyl group, and an optionally substituted unsaturated heterocyclic group in addition to one or more halogen atoms A linear, branched or cyclic alkenyl group having 2 to 6 carbon atoms substituted with a seed is shown.

The “optionally substituted C2-C6 alkynyl group” in R ₁ and R ₂ is an unsubstituted linear, branched or cyclic alkynyl group having 2 to 6 carbon atoms, or , A linear, branched or cyclic carbon substituted with at least one of a nitro group, an optionally substituted phenyl group, and an optionally substituted unsaturated heterocyclic group An alkynyl group having 2 to 6 atoms is shown. In addition, when there are two or more substituents, these substituents may be the same or different.
The “optionally substituted C2-C6 haloalkynyl group” in R ₁ and R ₂ is a linear, branched or cyclic carbon atom number 2 substituted only by one or more halogen atoms. -6 alkynyl groups, or at least one of a nitro group, an optionally substituted phenyl group, and an optionally substituted unsaturated heterocyclic group in addition to one or more halogen atoms A linear, branched or cyclic alkynyl group having 2 to 6 carbon atoms substituted with a seed is shown.

In the present invention, each of the substituents may further have a substituent if possible, and examples of the substituent are as follows.
Halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C9 cycloalkyl group, C3-C9 halocycloalkyl group, C2-C6 alkenyl group, C2-C6 haloalkenyl group, C2-C6 alkynyl group, C2 -C6 haloalkynyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkyl Sulfonyl group, C1-C6 haloalkylsulfonyl group, C2-C7 alkylcarbonyl group, C2-C7 haloalkylcarbonyl group, C2-C7 alkylcarbonyloxy group, C2-C7 haloalkylcarbonyloxy group, C1-C6 alkylsulfonyloxy group, C1- 6-haloalkylsulfonyloxy group, C2-C7 alkoxycarbonyl group, C2-C7 haloalkoxycarbonyl group, C2-C7 alkylcarbonylamino group, C2-C7 haloalkylcarbonylamino group, C2-C7 alkoxycarbonylamino group, C2-C7 haloalkoxy Carbonylamino group, C2-C7 alkylaminocarbonyl group, C2-C7 haloalkylaminocarbonyl group, C1-C6 alkylamino group, C1-C6 haloalkylamino group, C2-C6 alkenylamino group, C2-C6 haloalkenylamino group, C2 -C6 alkynylamino group, C2-C6 haloalkynylamino group, C3-C9 cycloalkylamino group, C3-C9 halocycloalkylamino group, C3-C7 alkenylaminocarbonyl group, C3-C7 halo Lucenylaminocarbonyl group, C3-C7 alkynylaminocarbonyl group, C3-C7 haloalkynylaminocarbonyl group, C4-C10 cycloalkylaminocarbonyl group, C4-C10 halocycloalkylaminocarbonyl group, amino group, carbamoyl group, sulfamoyl group A cyano group, a nitro group, a hydroxyl group, a carboxyl group, a pentafluorosulfanyl group, a phenyl group which may have a substituent, a heterocyclic group which may have a substituent, and a substituent. A benzyl group, a phenylcarbonyl group which may have a substituent, and a phenylamino group which may have a substituent. Each substituent may be the same or different.

  The amide derivatives represented by the general formula (1), general formula (7), and general formula (8) according to the present invention have one or more asymmetric carbon atoms or asymmetric in the structural formula. Although it may contain a center and there may be two or more optical isomers, the present invention includes all the optical isomers and mixtures containing them in an arbitrary ratio. The amide derivatives represented by the general formula (1), general formula (7), and general formula (8) according to the present invention include two types derived from a carbon-carbon double bond in the structural formula. Although the above geometric isomers may exist, the present invention includes all the geometric isomers and a mixture containing them in an arbitrary ratio.

Preferred substituents such as substituents in the amide derivative represented by the general formula (1) according to the present invention or combinations of atoms are as follows.
T is preferably -C (= G ₁ ) -Q ₁ , G ₁ is preferably an oxygen atom, and Q ₁ is preferably a phenyl group which may have a substituent or a substituent. a pyridyl group which may have a, more preferably as Q _1, has one or more substituents selected from halogen atoms, C1 haloalkyl group, a nitro group, and cyano group, there substituent is 2 or more In some cases, each substituent is the same or different phenyl group or pyridyl group.
G ₃ is preferably an oxygen atom.
R ₁ is preferably a hydrogen atom or a C1-C3 alkyl group.
R ₂ is preferably a hydrogen atom.
A is preferably a carbon atom, and K is preferably a nonmetallic atom group that forms a benzene ring with two carbon atoms to which A and A are bonded.
X is preferably a hydrogen atom, a halogen atom, or a cyano group, more preferably a hydrogen atom, a fluorine atom, or a cyano group.
When X is a substituent other than a hydrogen atom, n is preferably 0, 1 or 2.
Y ₁ is preferably a halogen atom or a C1-C3 haloalkyl group.
Y ₅ is preferably a C1-C3 haloalkyl group.
Y ₂ and Y ₄ are preferably a hydrogen atom, a halogen atom, or a C1-C4 alkyl group, and more preferably a hydrogen atom.
Y ₃ is preferably a C2-C5 haloalkyl group, and more preferably a C2-C4 perfluoroalkyl group.

Further, preferred substituents such as substituents in the amide derivative represented by the general formula (8) or combinations of atoms are as follows.
Q ₁ preferably has one or more substituents selected from a halogen atom, a C1 haloalkyl group, a nitro group, and a cyano group, and when there are two or more substituents, each substituent is the same. Or a phenyl group or a pyridyl group which may be different from each other.
R ₁ is preferably a hydrogen atom or a C1-C3 alkyl group.
R ₂ is preferably a hydrogen atom.
X ₁ and X ₂ are preferably a hydrogen atom or a fluorine atom, and X ₃ and X ₄ are preferably a hydrogen atom.
Y ₁ and Y ₅ are preferably a halogen atom or a C1-C3 haloalkyl group. Y ₂ and Y ₄ are preferably a hydrogen atom. Y ₃ is preferably a C3-C4 perfluoroalkyl group.

Although the typical manufacturing method of the amide derivative concerning this invention is shown below, the manufacturing method of the amide derivative concerning this invention is not limited to the manufacturing method shown below.
In general formulas shown in the following production methods, A, K, X, n, R ₁ , R ₂ , T, G ₃ , Y ₁ , Y ₂ , Y ₃ , Y ₄ , and Y ₅ are the above general formulas. (1) shows _{a, K, X, n,} R 1, R 2, T, G 3, Y 1, Y 2, Y 3, Y 4, and _{Y 5} and the same respectively in. LG represents a functional group having a leaving ability such as a halogen atom or a hydroxyl group, Hal represents a chlorine atom or a bromine atom, and Xa, Xb, and Xc represent a chlorine atom, a bromine atom, or an iodine atom.
<Manufacturing method 1>

1- (i): General formula (21) + General formula (22) → General formula (23)
General formula (21) + General formula (22) → General formula (28)
By reacting the nitroaromatic carboxylic acid derivative having a leaving group represented by the general formula (21) with the aromatic amine derivative represented by the general formula (22) in a suitable solvent or without solvent, A nitroaromatic carboxylic acid amide derivative represented by the general formula (23) or the general formula (28) can be produced. In this step, an appropriate base can be used.

  Any solvent that does not significantly inhibit the progress of this reaction may be used. For example, water, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as dichloromethane, chloroform and carbon tetrachloride, chain such as diethyl ether, dioxane, tetrahydrofuran and 1,2-dimethoxyethane or Cyclic ethers, esters such as ethyl acetate and butyl acetate, alcohols such as methanol and ethanol, ketones such as acetone, methyl isobutyl ketone and cyclohexanone, amides such as dimethylformamide and dimethylacetamide, nitriles such as acetonitrile, An inert solvent such as 1,3-dimethyl-2-imidazolidinone can be indicated. These solvents can be used alone or in combination of two or more.

Examples of the base include organic bases such as triethylamine, tri-n-butylamine, pyridine, and 4-dimethylaminopyridine, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, sodium hydrogen carbonate, and potassium carbonate. Carbonates, phosphates such as dipotassium monohydrogen phosphate and trisodium phosphate, alkali metal hydrides such as sodium hydride, alkali metal alcoholates such as sodium methoxide and sodium ethoxide, lithium diisopropylamide, etc. Lithium amides can be shown.
These bases may be appropriately selected and used within a range of 0.01 to 5 molar equivalents relative to the compound represented by the general formula (21).

What is necessary is just to select reaction temperature suitably in the range of the reflux temperature of the solvent to be used from -20 degreeC. The reaction time may be appropriately selected within the range of several minutes to 96 hours.
Among the compounds represented by the general formula (21), an aromatic carboxylic acid halide derivative can be easily produced from an aromatic carboxylic acid by a conventional method using a halogenating agent. Examples of the halogenating agent include halogenating agents such as thionyl chloride, thionyl bromide, phosphorus oxychloride, oxalyl chloride, and phosphorus trichloride.
On the other hand, it is possible to produce a compound represented by general formula (23) or general formula (28) from a nitroaromatic carboxylic acid derivative and a compound represented by general formula (22) without using a halogenating agent. It is. As the method, for example, Chem. Ber. The method described on page 788 (1970) can be mentioned. Specifically, a method using an additive such as 1-hydroxybenzotriazole as appropriate and using a condensing agent such as N, N′-dicyclohexylcarbodiimide can be shown. Examples of other condensing agents used in this case include 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide, 1,1′-carbonylbis-1H-imidazole, and the like.

Further, as another method for producing the compound represented by the general formula (23) or the general formula (28), a mixed acid anhydride method using chloroformates can also be shown. For example, J. et al. Am. Chem. Soc. The method described in page 5012 (1967) can be mentioned, and the compound represented by the general formula (23) or the general formula (28) can be produced. In this case, examples of the chloroformate used include isobutyl chloroformate and isopropyl chloroformate. In addition to the chloroformates, diethylacetyl chloride, trimethylacetyl chloride and the like can be used.
Both the method using a condensing agent and the mixed acid anhydride method are not limited to the solvent, reaction temperature, and reaction time described in the literature. As the solvent, an inert solvent that does not significantly inhibit the progress of the reaction may be used as appropriate. Further, the reaction temperature and reaction time may be appropriately selected according to the progress of the reaction.

1- (ii): General formula (23) → General formula (24)
General formula (28) → General formula (29)
The aromatic carboxylic acid amide derivative having a nitro group represented by general formula (23) or general formula (28) has an amino group represented by general formula (24) or general formula (29) by a reduction reaction. It can lead to an aromatic carboxylic acid amide derivative. Examples of the reduction reaction include a method using a hydrogenation reaction and a method using a metal compound (for example, stannous chloride (anhydride), iron powder, zinc powder, etc.).

  In the former method, the reaction can be carried out in a suitable solvent, in the presence of a catalyst, under normal pressure or under pressure, and in a hydrogen atmosphere. Examples of the catalyst include a palladium catalyst such as palladium-carbon, a nickel catalyst such as Raney nickel, a cobalt catalyst, a ruthenium catalyst, a rhodium catalyst, a platinum catalyst, and the like. Examples of the solvent include water, alcohols such as methanol and ethanol, benzene, Aromatic hydrocarbons such as toluene, chain or cyclic ethers such as ether, dioxane and tetrahydrofuran, and esters such as ethyl acetate can be used. What is necessary is just to select a pressure suitably in 0.1-10 Mpa and reaction temperature in the range of the reflux temperature of the solvent to be used from -20 degreeC. The reaction time may be appropriately selected within the range of several minutes to 96 hours. Thereby, the compound of General formula (24) or General formula (29) can be manufactured efficiently.

  The latter method is described in “Organic Synthesis” Coll. Vol. III P.I. According to the conditions described in 453, a method of using stannous chloride (anhydride) as a metal compound can be exemplified.

1- (iii): General formula (24) + General formula (26) → General formula (25)
By reacting the aromatic amine derivative represented by the general formula (24) and the carboxylic acid derivative represented by the general formula (26) or the carbonate ester derivative having a leaving group in an appropriate solvent, the general formula (25 Aromatic carboxylic acid amides or carbamate derivatives represented by In this step, an appropriate base or solvent can be used, and as the base or solvent, those exemplified in 1- (i) can be used. The reaction temperature, reaction time, etc. can also follow the example of 1- (i).
In the general formula (26), the carboxylic acid chloride derivative can be easily produced from the carboxylic acid derivative by a conventional method using a halogenating agent. As a halogenating agent, the example of 1- (i) can be followed.
There is also a method for producing the compound represented by the general formula (25) from the carboxylic acid derivative (26) and the compound represented by the general formula (24) without using a halogenating agent. It can be manufactured by following the method.

1- (iv): General formula (25) + General formula (27) → General formula (1)
By reacting the amide compound represented by the general formula (25) with a compound having a leaving group such as halogen represented by the general formula (27) in a solvent or without a solvent, the compound is represented by the general formula (1). Amide derivatives can be prepared. In this step, an appropriate base or solvent can be used, and as the base or solvent, those exemplified in 1- (i) can be used. The reaction temperature, reaction time, etc. can also follow the example of 1- (i).

1- (v): General formula (28) + General formula (30) → General formula (23)
By reacting the amide compound represented by the general formula (28) with a compound having a leaving group such as halogen represented by the general formula (30) in a solvent or without a solvent, the amide compound is represented by the general formula (23). Can be produced. In this step, an appropriate base or solvent can be used, and as the base or solvent, those exemplified in 1- (i) can be used. The reaction temperature, reaction time, etc. can also follow the example of 1- (i).

1- (vi): General formula (29) → General formula (31)
(Method A)
The compound represented by the general formula (29) is reacted with an aldehyde or a ketone in a solvent, a catalyst is added, and the reaction is performed in a hydrogen atmosphere to produce the compound represented by the general formula (31). be able to.
Any solvent may be used as long as it does not significantly inhibit the progress of this reaction. Examples thereof include aliphatic hydrocarbons such as hexane, cyclohexane, and methylcyclohexane, aromatic hydrocarbons such as benzene, xylene, and toluene, dichloromethane, and chloroform. Halogenated hydrocarbons such as carbon tetrachloride and 1,2-dichloroethane, ethers such as diethyl ether, dioxane, tetrahydrofuran and 1,2-dimethoxyethane, amides such as dimethylformamide and dimethylacetamide, acetonitrile, propio Nitriles such as nitriles, ketones such as acetone, methyl isobutyl ketone, cyclohexanone and methyl ethyl ketone, esters such as ethyl acetate and butyl acetate, 1,3-dimethyl-2-imidazolidinone, sulfolane and dimethyl ether Rusuruhokishido, alcohols such as methanol, ethanol, can indicate a solvent such as water, these solvents may be used alone or as a mixture of two or more.
Examples of the catalyst include palladium catalysts such as palladium-carbon and palladium hydroxide-carbon, nickel catalysts such as Raney nickel, cobalt catalysts, platinum catalysts, ruthenium catalysts, rhodium catalysts, and the like.

Examples of aldehydes include aldehydes such as formaldehyde, acetaldehyde, propionaldehyde, trifluoroacetaldehyde, difluoroacetaldehyde, fluoroacetaldehyde, chloroacetaldehyde, dichloroacetaldehyde, trichloroacetaldehyde, and bromoacetaldehyde.
Examples of ketones include ketones such as acetone, perfluoroacetone, and methyl ethyl ketone.
The reaction pressure may be appropriately selected in the range of 1 to 100 atm. What is necessary is just to select reaction temperature suitably in the range of the reflux temperature of the solvent to be used from -20 degreeC. The reaction time may be appropriately selected within the range of several minutes to 96 hours.

(Method B)
The compound represented by the general formula (31) can be produced by reacting the compound represented by the general formula (29) with aldehydes or ketones in a solvent and treating the reducing agent.
Any solvent may be used as long as it does not significantly inhibit the progress of this reaction. Examples thereof include aliphatic hydrocarbons such as hexane, cyclohexane, and methylcyclohexane, aromatic hydrocarbons such as benzene, xylene, and toluene, dichloromethane, and chloroform. Halogenated hydrocarbons such as carbon tetrachloride and 1,2-dichloroethane, ethers such as diethyl ether, dioxane, tetrahydrofuran and 1,2-dimethoxyethane, amides such as dimethylformamide and dimethylacetamide, acetonitrile, propio Nitriles such as nitriles, ketones such as acetone, methyl isobutyl ketone, cyclohexanone and methyl ethyl ketone, esters such as ethyl acetate and butyl acetate, 1,3-dimethyl-2-imidazolidinone, sulfolane and dimethyl ether Rusuruhokishido, alcohols such as methanol, ethanol, can indicate a solvent such as water, these solvents may be used alone or as a mixture of two or more.
Examples of the reducing agent include borohydrides such as sodium borohydride, sodium cyanoborohydride, and sodium triacetate borohydride.

Examples of aldehydes include aldehydes such as formaldehyde, acetaldehyde, propionaldehyde, trifluoroacetaldehyde, difluoroacetaldehyde, fluoroacetaldehyde, chloroacetaldehyde, dichloroacetaldehyde, trichloroacetaldehyde, and bromoacetaldehyde.
Examples of ketones include ketones such as acetone, perfluoroacetone, and methyl ethyl ketone.
What is necessary is just to select reaction temperature suitably in the range of the reflux temperature of the solvent to be used from -20 degreeC. The reaction time may be appropriately selected within the range of several minutes to 96 hours.

(Method C)
By reacting the compound represented by the general formula (29) with an aldehyde in a solvent or without a solvent, the compound of the general formula (31) can be produced.
Any solvent may be used as long as it does not significantly inhibit the progress of this reaction. Examples thereof include aliphatic hydrocarbons such as hexane, cyclohexane, and methylcyclohexane, aromatic hydrocarbons such as benzene, xylene, and toluene, dichloromethane, and chloroform. Halogenated hydrocarbons such as carbon tetrachloride and 1,2-dichloroethane, ethers such as diethyl ether, dioxane, tetrahydrofuran and 1,2-dimethoxyethane, amides such as dimethylformamide and dimethylacetamide, acetonitrile, propio Nitriles such as nitriles, ketones such as acetone, methyl isobutyl ketone, cyclohexanone and methyl ethyl ketone, esters such as ethyl acetate and butyl acetate, 1,3-dimethyl-2-imidazolidinone, sulfolane and dimethyl ether It can indicate alcohols such as sulfoxide, methanol and ethanol, inorganic acids such as sulfuric acid and hydrochloric acid, organic acids such as formic acid and acetic acid, and solvents such as water. These solvents can be used alone or in combination of two or more. can do.
Examples of aldehydes include formaldehyde, acetaldehyde, propionaldehyde, and the like.
The reaction temperature may be appropriately selected from −20 ° C. to the reflux temperature of the solvent used, and the reaction time may be selected from a range of several minutes to 96 hours.

1- (vii): General formula (31) + General formula (26) → General formula (32)
By reacting the aromatic amine derivative represented by the general formula (31) and the carboxylic acid derivative represented by the general formula (26) or the carbonate ester derivative having a leaving group in an appropriate solvent, the general formula (32 Aromatic carboxylic acid amides or carbamate derivatives represented by In this step, an appropriate base or solvent can be used, and as the base or solvent, those exemplified in 1- (i) can be used. The reaction temperature, reaction time, etc. can also follow the example of 1- (i).
In the general formula (26), the carboxylic acid chloride derivative can be easily produced from the carboxylic acid derivative by a conventional method using a halogenating agent. As a halogenating agent, the example of 1- (i) can be followed.
There is also a method for producing the compound represented by the general formula (32) from the carboxylic acid derivative (26) and the compound represented by the general formula (31) without using a halogenating agent. It can be manufactured by following the method.

1- (viii): General formula (32) + General formula (30) → General formula (1)
By reacting the amide compound represented by the general formula (32) and the compound represented by the general formula (30) having a leaving group such as a halogen in a solvent or without a solvent, the compound is represented by the general formula (1). Amide derivatives can be prepared. In this step, an appropriate base or solvent can be used, and as the base or solvent, those exemplified in 1- (i) can be used. The reaction temperature, reaction time, etc. can also follow the example of 1- (i).
<Manufacturing method 2>

2- (i): General formula (33) + General formula (22) → General formula (34)
By reacting the compound represented by the general formula (33) and the compound represented by the general formula (22) according to the conditions described in 1- (i), the compound represented by the general formula (34) is obtained. Can be manufactured.

2- (ii): General formula (34) → General formula (36)
For example, J. et al. Org. Chem. By following the conditions described on page 280 (1958), it is possible to carry out an amination reaction using an aminating agent such as ammonia to produce a compound represented by the general formula (36). Conditions such as the reaction solvent are not limited to those described in the literature, and an inert solvent that does not significantly inhibit the progress of the reaction may be used as appropriate. Further, the reaction temperature and reaction time may be appropriately selected according to the progress of the reaction. Examples of the aminating agent include methylamine, ethylamine and the like in addition to ammonia.

2- (iii): General formula (36) + General formula (26)-> General formula (1)
By reacting the compound represented by the general formula (36) and the compound represented by the general formula (26) according to the conditions described in 1- (i), an amide derivative represented by the general formula (1) Can be manufactured.
<Manufacturing method 3>

3- (i): General formula (29) + General formula (26) → General formula (35)
By reacting the aromatic amine derivative represented by the general formula (29) and the carboxylic acid derivative represented by the general formula (26) or the carbonate ester derivative having a leaving group in an appropriate solvent, the general formula (35 Aromatic carboxylic acid amides or carbamate derivatives represented by In this step, an appropriate base or solvent can be used, and as the base or solvent, those exemplified in 1- (i) can be used. The reaction temperature, reaction time, etc. can also follow the example of 1- (i).
In the general formula (26), the carboxylic acid chloride derivative can be easily produced from the carboxylic acid derivative by a conventional method using a halogenating agent. As a halogenating agent, the example of 1- (i) can be followed.
There is also a method for producing a compound represented by the general formula (35) from the carboxylic acid derivative (26) and the compound represented by the general formula (29) without using a halogenating agent. It can be manufactured by following the method.

3- (ii): General formula (35) + General formula (27) → General formula (1a)
By reacting the amide compound represented by the general formula (35) with a compound having a leaving group such as halogen represented by the general formula (27) in a solvent or without a solvent, the compound is represented by the general formula (1a). Amide derivatives can be prepared. In this step, an appropriate base or solvent can be used, and as the base or solvent, those exemplified in 1- (i) can be used. The reaction temperature, reaction time, etc. can also follow the example of 1- (i).
<Manufacturing method 4>

4- (i): General formula (24) → General formula (36)
By reacting according to the conditions of (Method A), (Method B) or (Method C) described in 1- (vi) using the compound represented by the general formula (24) as a starting material, the general formula (36) The compounds represented can be produced.

4- (i ′): General formula (24) + General formula (27) → General formula (36)
By reacting the aromatic amine derivative represented by the general formula (24) and the carboxylic acid derivative represented by the general formula (27) or the carbonate ester derivative having a leaving group in an appropriate solvent, the general formula (36 Can be produced. In this step, an appropriate base or solvent can be used, and as the base or solvent, those exemplified in 1- (i) can be used. The reaction temperature, reaction time, etc. can also follow the example of 1- (i).
In the general formula (27), the carboxylic acid chloride derivative can be easily produced from the carboxylic acid derivative by a conventional method using a halogenating agent. As a halogenating agent, the example of 1- (i) can be followed.
There is also a method for producing the compound represented by the general formula (36) from the carboxylic acid derivative (27) and the compound represented by the general formula (24) without using a halogenating agent. It can be manufactured by following the method.

4- (ii): General formula (36) + General formula (26) → General formula (1)
By reacting the compound represented by the general formula (36) and the compound represented by the general formula (26) as starting materials according to the conditions described in 1- (i), an amide represented by the general formula (1) Derivatives can be produced.
<Manufacturing method 5>

5- (i): General formula (37) + General formula (22) → General formula (38)
By reacting the compound represented by the general formula (37) and the compound represented by the general formula (22) according to the conditions described in 1- (i), the compound represented by the general formula (38) is obtained. Can be manufactured.

5- (ii): General formula (38) → General formula (39)
A compound represented by the general formula (39) is produced by reacting the nitroaromatic carboxylic acid amide derivative represented by the general formula (38) with a suitable fluorinating agent in a suitable solvent or without a solvent. can do.
Any solvent may be used as long as it does not significantly inhibit the progress of this reaction. For example, aliphatic hydrocarbons such as hexane, cyclohexane, and methylcyclohexane, aromatic hydrocarbons such as benzene, toluene, and xylene, dichloromethane, chloroform, and the like. Halogenated hydrocarbons such as carbon tetrachloride and 1,2-dichloroethane, chain or cyclic ethers such as diethyl ether, dioxane, tetrahydrofuran and 1,2-dimethoxyethane, esters such as ethyl acetate and butyl acetate, Ketones such as acetone, methyl isobutyl ketone, cyclohexanone, methyl ethyl ketone, nitriles such as acetonitrile, propionitrile, 1,3-dimethyl-2-imidazolidinone, sulfolane, dimethyl sulfoxide, N, N-dimethylformamide , N- methylpyrrolidone, N, can show aprotic polar solvents such as N- dimethylacetamide, these solvents may be used alone or as a mixture of two or more.

As the fluorinating agent, 1,1,2,2-tetrafluoroethyldiethylamine, 2-chloro-1,1,2-trifluoroethyldiethylamine, trifluorodiphenylphosphorane, difluorotriphenylphosphorane, fluoroformate esters, Sulfur tetrafluoride, potassium fluoride, potassium hydrogen fluoride, cesium fluoride, rubidium fluoride, sodium fluoride, lithium fluoride, antimony fluoride (III), antimony fluoride (V), zinc fluoride, fluoride Cobalt, lead fluoride, copper fluoride, mercury fluoride (II), silver fluoride, silver fluoroborate, thallium fluoride (I), molybdenum fluoride (VI), arsenic fluoride (III), bromine fluoride, Selenium tetrafluoride, tris (dimethylamino) sulfonium difluorotrimethylsilicate, sodium hexafluorosilicate, quaternary fluoride Monium, (2-chloroethyl) diethylamine, diethylaminosulfur trifluoride, morpholinosulfur trifluoride, silicon tetrafluoride, hydrogen fluoride, hydrofluoric acid, hydrogen fluoride pyridine complex, hydrogen fluoride triethylamine complex, fluoride Hydrogen salts, bis (2-methoxyethyl) aminosulfur trifluoride, 2,2-difluoro-1,3-dimethyl-2-imidazolidinone, iodine pentafluoride, tris (diethylamino) phosphonium-2,2,3 3,4,4-hexafluoro-cyclobutane ylide, triethylammonium hexafluorocyclobutane ylide, hexafluoropropene and the like can be shown. These fluorinating agents can be used alone or in combination of two or more.
These fluorinating agents may be appropriately selected and used as a solvent in the range of 1 to 10-fold molar equivalent to the nitroaromatic carboxylic acid amide derivative represented by the general formula (38).

An additive may be used. Examples of the additive include crown ethers such as 18-crown-6, phase transfer catalysts such as tetraphenylphosphonium salts, non-base salts such as calcium fluoride and calcium chloride, oxidation Metal oxides such as mercury, ion exchange resins and the like can be shown, and these additives can be used not only in the reaction system but also as a pretreatment agent for the fluorinating agent.
What is necessary is just to select reaction temperature suitably in the range of the reflux temperature of the solvent to be used from -80 degreeC. The reaction time may be appropriately selected within the range of several minutes to 96 hours.
<Manufacturing method 6>

6- (i): General formula (40) + General formula (22) → General formula (41)
By reacting the compound represented by the general formula (40) and the compound represented by the general formula (22) according to the conditions described in 1- (i), the compound represented by the general formula (41) is obtained. Can be manufactured.

6- (ii): General formula (41) → General formula (42)
The compound represented by the general formula (42) is produced by reacting the halogen aromatic carboxylic acid amide derivative represented by the general formula (41) with a suitable cyanating agent in a suitable solvent or without a solvent. be able to.
Any solvent that does not significantly inhibit the progress of this reaction may be used. For example, aliphatic hydrocarbons such as hexane, cyclohexane and methylcyclohexane, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride and 1,2-dichloroethane, Chain or cyclic ethers such as diethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, esters such as ethyl acetate and butyl acetate, ketones such as acetone, methyl isobutyl ketone, cyclohexanone and methyl ethyl ketone, acetonitrile, propio Nitriles such as nitriles, 1,3-dimethyl-2-imidazolidinone, sulfolane, dimethyl sulfoxide, N, N-dimethylformamide, N-methylpyrrolidone, N, N-dimethylacetamide, etc. Can show protic polar solvents, these solvents may be used alone or as a mixture of two or more.

Examples of cyanating agents include cyanide salts such as sodium cyanide, potassium cyanide and sodium cyanoborohydride, metal cyanides such as copper cyanide, silver cyanide and lithium cyanide, hydrogen cyanide and tetraethylammonium cyanide. It can be illustrated.
These cyanating agents may be appropriately selected and used within a range of 1 to 10-fold molar equivalents relative to the halogen aromatic carboxylic acid amide derivative represented by the general formula (41).
An additive may be used, and examples of the additive include crown ethers such as 18-crown-6, phase transfer catalysts such as tetraphenylphosphonium salts, and basic salts such as sodium iodide. .
What is necessary is just to select reaction temperature suitably in the range of the reflux temperature of the solvent to be used from -20 degreeC. The reaction time may be appropriately selected within the range of several minutes to 96 hours.
<Manufacturing method 7>

7- (i): General formula (43) → General formula (44)
By reacting the compound represented by general formula (43) with Lawesson's reagent in accordance with known conditions described in Synthesis 463 pages (1993), Synthesis 829 pages (1984), etc., general formula (44) The compounds represented can be produced. Conditions such as solvent and reaction temperature are not limited to those described in the literature.

2- (ii): General formula (44) + General formula (26) → General formula (45)
By reacting the compound represented by the general formula (44) and the compound represented by the general formula (26) according to the conditions described in 1- (i), the compound represented by the general formula (45) is obtained. Can be manufactured.
<Manufacturing method 8>

8: General formula (46) → General formula (47) + General formula (48)
From the compound represented by the general formula (46), the compound represented by the general formula (47) and the general formula (48) can be produced according to the conditions described in 7- (i). Conditions such as solvent and reaction temperature are not limited to those described in the literature. These two compounds can be easily separated and purified by a known separation and purification technique such as silica gel column chromatography.
<Manufacturing method 9>

9- (i): General formula (49) + General formula (26) → General formula (50)
By using the carboxylic acid having an amino group represented by the general formula (49) as a starting material and reacting with the compound represented by the general formula (26) according to the conditions described in 1- (i), the general formula ( 50) Carboxylic acids having an acylamino group represented by 50) can be produced.

9- (ii): General formula (50) → General formula (51)
The compound represented by the general formula (50) is reacted with thionyl chloride, oxalyl chloride, phosgene, phosphorus oxychloride, phosphorus pentachloride, phosphorus trichloride, thionyl bromide, phosphorus tribromide, diethylaminosulfur trifluoride and the like. The compound represented by the general formula (51) can be produced by a known ordinary method.

9- (iii): General formula (51) + General formula (22) → General formula (1)
By reacting the compound represented by the general formula (51) and the compound represented by the general formula (22) according to the conditions described in 1- (i), the compound represented by the general formula (1) Can be manufactured.

9- (iv): General formula (50) + General formula (22) → General formula (1)
The compound represented by the general formula (50) is reacted with the compound represented by the general formula (22) according to the conditions using the condensing agent described in 1- (i) or the conditions using the mixed acid anhydride method. Thus, the amide derivative represented by the general formula (1) can be produced.

  In all the production methods shown above, the target product may be isolated from the reaction system according to a conventional method after completion of the reaction. can do. Moreover, it is also possible to use for the next reaction process, without isolating a target object from a reaction system.

Tables 1 to 51 below show amide derivatives represented by the general formula (1), the general formula (7), or the general formula (8), which are active ingredients of the insect control composition for plant seeds of the present invention. Although representative compound examples are shown, the present invention is not limited to these.
In the table, “n-” is normal, “i-” is iso, “s-” is secondary, “t-” is tertiary, “Me” is methyl group, “Et” is “N-Pr” is a normal propyl group, “i-Pr” is an isopropyl group, “n-Bu” is a normal butyl group, “i-Bu” is an isobutyl group, “s-Bu”. "Is a secondary butyl group," t-Bu "is a tertiary butyl group," CF3 "is a trifluoromethyl group," C2F5 "is a pentafluoroethyl group," n-C3F7 "is a heptafluoronormal propyl group. "I-C3F7" represents a heptafluoroisopropyl group, "OCF3" represents a trifluoromethoxy group, "OC2F5" represents a pentafluoroethoxy group, "H" represents a hydrogen atom, "F" represents a fluorine atom, "C "Is a chlorine atom," Br "is a bromine atom," I "is an iodine atom," O "is an oxygen atom," C (O) "is a carbonyl group," CN "is a cyano group, “Py” represents a pyridyl group, “Ph” represents a phenyl group, and “S (O) 2” represents a sulfonyl group.

Table 52 shows physical property values of typical compounds of the amide derivatives according to the present invention. The chemical shift value of ¹ H-NMR shown here is a value using tetramethylsilane as an internal reference material unless otherwise specified.

  Specific examples of insect damage that can be prevented by using the plant seed insect control composition of the present invention include, for example, teaberry leafworm (Adoxophyes honmai), apple leafberry leaflet (Adoxophyes orana faciata), apple leafberry leaflet (Archips breviplicanus) ), Apple sash moth (Grapholita inopinata), green squirrel (Archips fuscocupreanus), pear squirrel (Grapholita molesta), chahamaki (Choristoneura magnanima), bean squirrel (Leguminivora glycinivorella), mulberry scorpion (Oleth mute sap) ), Apple gypsy moth (Argyresthia conjugella), sprerrina astaurota, bean squirrel (Matsumuraeses phaseoli), pandemis heparana, bucculatrix pyrivorella, peach moth carp , Ginmon humiligus (Lyonetia pr unifoliella malinella, Caloptilia theivora, Golden moth (Phyllonorycter ringoniella), Citrus (Phyllocnistis citrella), Green moth (Acrolepiopsis sapporensis), Wild moth (Acrolepiopsis suzukiella moth, Locust) Helcystogramma triannulella), cotton beetle (Pectinophora gossypiella), peach sinker moth (Carposina sasakii), green moth (Chilo suppressalis), white-necked moth (Cnaphalocrocis medinalis), chamadara moth (Ephestia elutella), peach moth indica), Etiella zinckenella, Glyphodes pyloalis, Scirpophaga incertulas, Hellula undalis, Ostrinia furnacalis, Ostrinia nia scapulalis), white-spotted moth (Parapediasia teterrella), green sedge (Parnara guttata), white-tailed butterfly (Pieris brassicae), white-winged butterfly (Pieris rapae crucivora), swallowtail butterfly (Papilio xuthus), mugwort sari Chadokuga (Euproctis pseudoconspersa), gypsy moth (Lymantria dispar), Japanese horned squirrel (Orgyia thyellina), white-spotted starfish (Hyphantria cunea), stag beetle (Lemyra imparilis), Akebiko-noha (Adris tyrannus) ipsilon, cabbage moth (Agrotis segetum), Tamanaginuwaba (Autographa nigrisigna), honey beetle (Ctenoplusia agnata), codlinga (Cydla pomonella), cigarette moth (Helicoverpa armigera), tobacco moth (Helicoverpa asszea), cotton ball worm (coverball worm) Tobacco bad Heliothis virescens, European corn borer (Ostrinia nubilalis), Mamestra brassicae, Mythimna separata, Seiami inferens, Naraa aenescens, Southern opt iera, pod S opt ), Fall army worms (Spodoptera frugiperda), cotton leaf worms (Spodoptera littoralis), cutworm (Spodoptera litura), Spodoptera depravata, nettle worm (Trichoplusia ni), grapeberry moss (Endopiza vite) Manduca quinquemaculata), Lepidoptera insects such as tobacco hornworm (Manduca sexta),

Arboridia apicalis, Midorinaga leafhopper (Balclutha saltuella), Phalatenus leafamine (Epiacanthus stramineus), Potato leaf hopper (Empoasca fabae), Persian leafhopper (Empoasca nipponica), Chanomidorimpoisca , Peanut leafhopper (Empoasca sakaii), leafhopper leafhopper (Macrosteles striifrons), leafhopper leafhopper (Nephotettix cinctinceps), cotton-free hopper (Psuedatomoscelis seriatus) ), Orange lice (Diaphorina citri), psylla pyrisuga, citrus whiteflies (Aleurocanthus spiniferus), silver leaf whiteflies (Bemisia argentifolii), tobacco whiteflies (Bemisia tabaci), citrus whitefly tri urodes vaporariorum, grape whitefly (Aleurolobus taonabae), grape aphid (Viteus vitifolii), black aphid (Lipaphis erysimi), cotton aphid (Aphis gossypii), snowy yellow aphid (Aphis spiraecola), peach worm aphid Aphids (Toxoptera aurantii), Drosicha corpulenta, Icerya purchasi, Phenacoccus solani, Pulvinaria aurantii, Citrus cicus, Oc Pseudaonidia duplex), Fujicona scale insect (Planococcus kuraunhiae), stag beetle scale (Pseudococcus comstocki), pear scale insect (Comstockaspis perniciosa), horn beetle (Ceroplastes ceriferus), ruby rotifer (Ceroplastes idium aurur) i), tea scale (Fiorinia theae), chano marine scale (Pseudaonidia paeoniae), stag beetle (Pseudaulacaspis pentagona), scallop scale (Pseudaulacaspis prunicola), scallop scale (Unaspis euonymi) Japanese whitebug (Cimex lectularius), spotted beetle (Dolycoris baccarum), sea turtle (Eurydema rugosum), bark beetle (Eysarcoris aeneus), bark beetle (Eysarcoris lewisi), vent Haremorpha halys, Nezara antennata, Nezara viridula, Piezodorus hybneri, Plautia crossota, Rino phor, Scot Cletus punctiger) Reptocorisa chinensis, Riptortus clavatus, Red-footed beetle (Rhopalus msculatus), Cavelerius saccharivorus, Togo hemipterus, cing D-tus (Stephanitis pyrioides), black-headed turtle (Halticus insularis), finished plant bug (Lygus lineolaris), long-horned turtle (Stenodema sibiricum), red-eared turtle (Stenotus rubrovittatus), half-spotted turtle (Trigonotylus cael) Lepidoptera,

Douganebubui (Anomala cuprea), Japanese squirrel (Anomala rufocuprea), Coreo hanumuri (Gametis jucunda), Nagachakogane (Heptophylla picea), Japanese beetle (Popillia japonica), Colorado potato beetle (Lepinotarsa decemlineata), tis Melanonotus fortnumi, Melanonotus tamsuyensis, Tobacco beetle (Lasioderma serricorne), Lyctusbrunneus, Minami beetle (Tomicus piniperda), Dominant operidae Common beetle (Epilachna varivestis), tiger beetle (Epilachna vigintioctopunctata), white-footed beetle (Tenebrio molitor), red-footed beetle (Tribolium castaneum), red-horned beetle (Anoplophora malasiaca), pine beetle (Anoplophora malasiaca) tus), yellowtail beetle (Psacothea hilaris), grape tiger beetle (Xylotrechus pyrrhoderus), azuki beetle (Callosobruchus chinensis), cucumber beetle (Aulacophora femoralis), rice beetle (Oulema oryzae), tencito beetle (cinae) (Diabrotica undecimpunctata), Western corn rootworm (Diabrotica virgifera), Northern corn rootworm (Diabrotica barberi), Phyllotreta striolata, Psylliodes angusticollis, Psylliodes angusticollis, Rhynchites Cylas formicarius), cotton weevil (Anthonomus grandis), weevil (Echinocnemus squameus), weevil (Euscepes postfasciatus), alfalfa weevil (Hypera postica), squirrel weevil (Lissohoptrus oryzophilus), chinske sul ), Granary weevil (Sitophilus granarius), weevil (Sitophilus zeamais), hornet weevil (Sphenophorus venatus vestitus), Coleoptera (Paederus fuscipes), etc.,

Thrips haemorrhoidal (Frankliniella intonsa), Thrips flavus, Thrips sci ), Coleoptera thrips (Ponticulothrips diospyrosi), etc.
Soybean flies (Asphondylia yushimai), mud wings (Sitodiplosis mosellana), fruit flies (Bactrocera cucurbitae), citrus fruit flies (Bactrocera dorsalis), citrus fruit flies (Ceratitis capitata), rice moth flies Leafhopper (Agromyza oryzae), Leafworm (Chromatomyia horticola), Eggplant leaffly (Liriomyza bryoniae), Leafy leaffly (Liriomyza chinensis), Tomato leaffly (Liriomyza sativae), Beanworm (Liriomyza dwarf) ), Sugar beetle (Pegomya cunicularia), apple maggot (Rhagoletis pomonella), hessian fly (Mayetiola destructor), housefly (Musca domestica), flies (Stomoxys calcitrans), sheep flies (Melophagus ovinus), pod fly Drosophila (Hypoderma lineatum), sheep flies (Oestrus ovis), tsetse flies (Glossina palpalis, Glossina morsitans), yellowtail (Prosimulium yezoensis), bullfly (Tabanus trigonus), Culex flies (Telmatoscopus albipunctatus), nigrum (Telmatoscopus albipunctatus) pallens), Aedes aegypti, Aedes albopicutus, Anopheles hyracanus sinesis, etc.,

Bumblebee (Apethymus kuri), Bumblebee (Athalia rosae), Bumblebee (Arge pagana), Bumblebee (Neodiprion sertifer), Bumblebee (Dryocosmus kuriphilus), Gantai (Eciton burchelli, Eciton schmitus), Eciton burchelli, Eciton schmitus mandarina), bulldog ant (Myrmecia spp.), fire ant (Solenopsis spp.), pharaoh ant (Monomorium pharaonis), etc.
Straight-legged insects, such as Teleogryllus emma, Kera (Gryllotalpa orientalis), Tosama grasshopper (Locusta migratoria), Oxya yezoensis, Sabaquat grasshopper (Schistocerca gregaria),
Coleoptera insects such as the white-headed beetle (Onychiurus folsomi), the Siberian white-headed beetle (Onychiurus sibiricus), the Bourletiella hortensis,
Nettle insects such as black cockroach (Periplaneta fuliginosa), cockroach (Periplaneta japonica), German cockroach (Blattella germanica), cockroach (Periplaneta Americana),
Termite insects such as the termites (Coptotermes formosanus), Yamato termites (Reticulitermes speratus), Taiwan termites (Odontotermes formosanus),
Insect insects such as cat fleas (Ctenocephalidae felis), dog fleas (Ctenocephalides canis), chicken fleas (Echidnophaga gallinacea), human fleas (Pulex irritans), keops rat fleas (Xenopsylla cheopis),
Insects such as chicken lice (Menacanthus stramineus) and bovine lice (Bovicola bovis),
Lice insects such as cattle lice (Haematopinus eurysternus), pig lice (Haematopinus suis), cattle white lice (Linognathus vituli), horned lice (Solenopotes capillatus),

Dust mites such as cyclamen dust mite (Phytonemus pallidus), chano mite mite (Polyphagotarsonemus latus), and mites (Tarsonemus bilobatus),
Spider mites (Penthaleus erythrocephalus), wheat mites (Penthaleus major), etc.
Spider mites such as rice spider mite (Oligonychus shinkajii), citrus spider mite (Panonychus citri), blue spider mite (Panonychus mori), apple spider mite (Panonychus ulmi), Kanzawa spider mite (Tetranychus kanzawai), spider mite (Tetranychus urticae), etc.
Chinese cabbage mite (Acaphylla theavagrans), tulip rust mite (Aceria tulipae), tomato rust mite (Aculops lycopersici), citrus red mite (Aculops pelekassi), apple rust mite (Aculus schlechtendali), black rust mite (Eriophyes chitrastrostrum) ), Etc.,
Acarids such as robin mite (Rhizoglyphus robini), mushroom mite (Tyrophagus putrescentiae), spinach mushroom mite (Tyrophagus similis),
Bee mites such as honeybee mite (Varroa jacobsoni),
Tick tick (Boophilus microplus), Rhipicephalus sanguineus, Tick tick (Haemaphysalis longicornis), Tick tick (Haemophysalis flava), Tick tick (Haemophysalis campanulata), Tick tick (Ixo tus tick) Amblyomma spp.), Ticks such as Dermacentor spp.
Claw mites (Cheyletiella yasguri), claw mites (Cheyletiella blakei),
Acne mites, such as Inodecarid mites (Demodex canis), Caterpillar mites (Demodex cati),
Cucumber mites such as sheep cucumber mites (Psoroptes ovis),
Spider mites, such as Sarcoptes scabiei, Caterpillar spider mite (Notoedres cati), Chicken spider mite (Knemidocoptes spp.),
Crustaceans such as the armadillum (Armadillidium vulgare),
Gastropods such as Pomacea canaliculata, African mussel (Achatina fulica), Slug (Meghimatium bilineatum), Chaukoura slug (Limax Valentiana), Uskawamai (Acusta despecta sieboldiana), Mishamai mai (Euhadra peliomphala), etc.
Southern nematode nematode (Prathylenchus coffeae), Kitane-negususa nematode (Prathylenchus penetrans), Kurume rushes nematode (Prathylenchus vulnus), potato cyst nematode (Globodera rostochiensis), soybean cyst nematode (Heterodera lypter Nematodes such as root-knot nematode (Meloidogyne incognita), rice-spotted nematode (Aphelenchoides besseyi), pine wood nematode (Bursaphelenchus xylophilus),
However, the present invention is not limited to these.

  By applying the insect control composition for plant seeds of the present invention to plant seeds, it is possible to prevent damage caused by the insects occurring in the plant after sowing. That is, the insect pest control composition of the present invention is sprayed, smeared, soaked or powdered on the plant seeds in an amount effective for pest control as it is, or appropriately diluted with water or suspended. By treating, plant seeds may be contacted with an amide derivative effective for preventing insect damage.

  By applying the insect pest control composition of the present invention to plant seeds, it is possible to control pests generated during the storage of plant seeds. That is, the insect control composition of the present invention is sprayed, sprayed, applied, or applied to a plant seed or a plant seed storage site in an amount effective for pest control as it is, or appropriately diluted or suspended with water or the like. What is necessary is just to perform processing, such as spraying, application | coating, immersion, powder coating, or smoke / fumigation.

  Plant seeds refer to those that store nutrients for germination of young plants and are used for agricultural reproduction. For example, seeds such as corn, soybeans, red beans, cotton, rice, sugar beet, wheat, barley, sunflower, tomato, cucumber, eggplant, spinach, sweet pea, pumpkin, sugar cane, tobacco, sweet pepper, rape, sweet potato , Seed seeds such as konjac, edible lily, bulbs such as tulips and seed balls such as raccoon. These plant seeds may be transformed. A transformed plant refers to a plant that has been created by artificially manipulating genes and the like and does not exist in nature. For example, soybean, corn, cotton, etc. imparted with herbicide resistance, rice, tobacco, etc. adapted to cold regions, corn, cotton, potato, etc., imparted with the ability to produce insecticides.

  Although the dilution rate of the insect-controlling composition of the present invention is appropriately selected depending on the crop to be applied and insect damage, it is usually selected from the range of 1 to 10,000 times.

The amount used when the insect damage control composition of the present invention is powdered, sprayed or smeared on plant seeds is usually about 0.05 to 5% of the dry plant seed weight. The amount used is not limited to these ranges, and may vary depending on the form of the preparation and the type of plant seed to be treated.
In general, the insect-controlling composition of the present invention is formulated and used in a convenient form in accordance with a conventional formulation method for agricultural and horticultural drugs. That is, these are mixed in a suitable inert carrier, or if necessary, together with an auxiliary agent in a suitable ratio, dissolved, separated, suspended, mixed, impregnated, adsorbed or adhered, and an appropriate dosage form, for example, , Suspensions, emulsions, liquids, wettable powders, granules, powders, flowables, tablets and the like.

  The content of the amide derivative effective for prevention of insect damage in the insect control composition of the present invention is usually 0.5 to 20% by weight for powders, 5 to 50% by weight for emulsions, 10 to 90% by weight for wettable powders, 0.1-20% by weight for granules and 10-90% by weight for flowable formulations. On the other hand, the amount of carrier in each dosage form is usually 60 to 99% by weight for powders, 40 to 95% by weight for emulsions, 10 to 90% by weight for wettable powders, 80 to 99% by weight for granules, and flowable preparations Is 10 to 90% by weight. The amount of the auxiliary agent is usually 0.1 to 20% by weight for powders, 1 to 20% by weight for emulsions, 0.1 to 20% by weight for wettable powders, 0.1 to 20% by weight for granules, and In the flowable preparation, it is 0.1 to 20% by weight.

  The inert carrier may be either solid or liquid, and examples of materials that can be a solid inert carrier include soy flour, cereal flour, wood flour, bark flour, saw flour, tobacco stem flour, walnut Shell powder, bran, fiber powder, residues after extraction of plant extracts, synthetic polymers such as ground synthetic resin, clays (eg kaolin, bentonite, acid clay), talc (eg talc, pyrophyllide, etc.), silicas (For example, diatomaceous earth, silica sand, mica, white carbon (some synthetic high-dispersed silicic acid, also called hydrous fine silicon, hydrous silicic acid, and some products contain calcium silicate as a main component)), activated carbon, sulfur powder, pumice, calcined diatomaceous earth , Brick minerals, fly ash, sand, calcium carbonate, calcium phosphate and other inorganic mineral powders, ammonium sulfate, phosphorous, ammonium nitrate, urea, salt, etc. Manabu fertilizers, etc. can be mentioned compost, which are used alone or in the form of a mixture of two or more.

  As materials that can be used as a liquid inert carrier, in addition to those having solvent ability, amide derivatives that are effective in controlling pests can be dispersed with the aid of an auxiliary agent without having solvent ability. For example, the following carriers may be used as representative examples, and these may be used alone or in the form of a mixture of two or more, such as water, alcohols (for example, methanol, ethanol, isopropanol, butanol, ethylene). Glycol, etc.), ketones (eg acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone etc.), ethers (eg diethyl ether, dioxane, cellosolve, diisopropyl ether, tetrahydrofuran etc.), aliphatic hydrocarbons (eg kerosene, Mineral oil) Aromatic hydrocarbons (eg, benzene, toluene, xylene, solvent naphtha, alkylnaphthalene, etc.), halogenated hydrocarbons (eg, dichloromethane, chloroform, carbon tetrachloride, chlorobenzene, etc.), esters (eg, ethyl acetate, butyl acetate, Examples thereof include ethyl propionate, diisobutyl phthalate, dibutyl phthalate, dioctyl phthalate, etc.), amides (eg dimethylformamide, diethylformamide, dimethylacetamide etc.) and nitriles (eg acetonitrile).

  As the auxiliary agent, typical auxiliary agents exemplified below can be exemplified, and these auxiliary agents are used depending on the purpose, and are used alone or in some cases, in combination with two or more auxiliary agents. In some cases, it is possible to use no adjuvant.

  Surfactants are used for the purpose of emulsifying, dispersing, solubilizing and / or wetting amide derivatives effective in preventing insect damage, such as polyoxyethylene alkyl ethers, polyoxyethylene alkyl aryl ethers, polyoxyethylene higher grades. Surface activity such as fatty acid ester, polyoxyethylene resin acid ester, polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monooleate, alkylaryl sulfonate, naphthalene sulfonate, lignin sulfonate, higher alcohol sulfate Agents can be indicated.

  Further, for the purpose of dispersion stabilization, adhesion and / or binding of amide derivatives effective for prevention of insect damage, the following auxiliary agents can be used, for example, casein, gelatin, starch, methylcellulose, carboxy Adjuvants such as methylcellulose, gum arabic, polyvinyl alcohol, pine oil, coconut oil, bentonite, xanthan gum, lignin sulfonate can be used.

  In order to improve the fluidity of solid products, the following adjuvants may be used, and for example, adjuvants such as waxes, stearates and alkyl phosphates may be used. As a peptizer for the suspension product, for example, auxiliary agents such as naphthalenesulfonic acid condensate and condensed phosphate can be used. As the antifoaming agent, for example, an auxiliary agent such as silicone oil can be used.

  The insect-controlling composition of the present invention is stable to light, heat, oxidation, etc., but if necessary, an antioxidant or an ultraviolet absorber such as BHT (2,6-di-t-butyl-4-methylphenol). ), Phenol derivatives such as BHA (butylhydroxyanisole), bisphenol derivatives, and arylamines or benzophenone compounds such as phenyl-α-naphthylamine, phenyl-β-naphthylamine, phenetidine and acetone condensates as stabilizers. By adding an appropriate amount, a more stable composition can be obtained.

The following examples illustrate typical examples of amide derivatives according to the present invention, but the present invention is not limited to these examples. In this example, DMF means N, N-dimethylformamide, THF means tetrahydrofuran, IPE means isopropyl ether, DMI means 1,3-dimethyl-2-imidazolidinone, DMSO means dimethyl sulfoxide, respectively. .
Unless otherwise specified, “%” is based on mass.

<Example 1>
N- (2-Bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -2-fluoro-3- (N-methylbenzamido) benzamide (Compound No. 7-1574) Manufacturing.

<1-1>
Preparation of 4- (perfluoropropan-2-yl) -2- (trifluoromethyl) aniline

Mixing 100 g (0.608 mol) of 2- (trifluoromethyl) aniline, 131 g (0.639 mol) of 85% hydrosulfite sodium, 20.9 g (0.0608 mol) of tetrabutylammonium hydrogen sulfate with 1500 ml of ethyl acetate and 1500 ml of water The solution was charged and 53.9 g (0.639 mol) of sodium bicarbonate was added. 198 g (0.669 mol) of heptafluoroisopropyl iodide was added dropwise at room temperature, and the mixture was stirred at room temperature for 6 hours. After separation, the solvent of the organic layer was distilled off under reduced pressure, and 500 ml of ethyl acetate was charged. 160 g (0.608 mol) of 4M hydrogen chloride / ethyl acetate solution was added dropwise, and the mixture was stirred at room temperature for 30 minutes, and then stirred at 5 ° C. for 1 hour. After filtration, the filtrate was washed successively with water and saturated aqueous sodium hydrogen carbonate solution and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (developing solvent; hexane: ethyl acetate = 10: 1) to produce 60.0 g (yield 30%) of the title compound.
¹ H-NMR (CDCl ₃ , ppm) δ 4.49 (2H, broadcast-s), 6.81 (1H, d, J = 8.3 Hz), 7.48 (1H, d, J = 8.3 Hz) , 7.64 (1H, s).

<1-2>
Preparation of 2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) aniline

4- (Perfluoropropan-2-yl) -2- (trifluoromethyl) aniline (100 g, 0.273 mol) was charged into DMF (500 ml), and N-bromosuccinimide (52.1 g, 0.287 mol) was added for 30 minutes. It was divided and charged over time. After stirring at 60 ° C. for 2 hours, the mixture was cooled to room temperature and discharged into 2000 ml of water. The mixture was extracted with ethyl acetate, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (developing solvent; hexane: ethyl acetate = 20: 1) to produce 89.0 g (yield 80%) of the title compound. did.
¹ H-NMR (CDCl ₃ , ppm) δ 5.03 (2H, broadcast-s), 7.61 (1H, s), 7.79 (1H, s).

<1-3>
Preparation of N- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -2-chloro-3-nitrobenzamide

2-Bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) aniline 3.60 g (8.82 mmol) was charged into 20 ml of dehydrated THF and cooled to -70 ° C. in a nitrogen atmosphere. . 2.34 g of acid chloride prepared from 2-chloro-3-nitrobenzoic acid and thionyl chloride dissolved in 5 ml of dehydrated THF was added dropwise 4.85 ml (9.70 mmol) of 2.0 M lithium diisopropylamide hexane solution. (10.7 mmol) was added dropwise, and the mixture was stirred at -70 ° C for 30 minutes, and then stirred at room temperature for 30 minutes. After discharging into an aqueous ammonium chloride solution, the mixture was extracted with ethyl acetate and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (developing solvent; hexane: ethyl acetate = 10: 1 → 8: 2 → 3: 1) to give 1.76 g of the title compound. (Yield: 34%) was produced.
¹ H-NMR (CDCl ₃ , ppm) δ 7.61 (1H, t, J = 7.8 Hz), 7.67 (1H, broadcast-s), 7.93-7.97 (3H, m), 8 .18 (1H, broadcast-s).

<1-4>
Preparation of N- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -2-fluoro-3-nitrobenzamide

Under a nitrogen stream, 4.89 g (8.27 mmol) of N- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -2-chloro-3-nitrobenzamide To 50 ml of dehydrated DMF solution, 2.40 g (41.3 mmol) of potassium fluoride (spray dry product) was added and stirred at 130 ° C. for 10 hours. Ethyl acetate, hexane, and water were added to the reaction solution and the phases were separated, and the organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The residue obtained by distilling off the solvent under reduced pressure was purified by silica gel column chromatography (developing solvent; hexane: ethyl acetate = 10: 1) to obtain 0.940 g (yield 20%) of the title compound. Manufactured.
¹ H-NMR (CDCl ₃ , ppm) δ 7.53 (1H, t, J = 7.3 Hz), 7.93 (1H, broadcast-s), 8.17-8.18 (2H, m), 8 .28-8.32 (1H, m), 8.44-8.48 (1H, m).

<1-5>
Preparation of 3-amino-N- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -2-fluorobenzamide

N- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -2-fluoro-3-nitrobenzamide 0.940 g (1.63 mmol), stannous chloride (Anhydrous) 0.960 g (5.05 mmol) was added to 10 ml of ethanol, then 1.02 ml (9.78 mmol) of concentrated hydrochloric acid was added, and the mixture was stirred at 60 ° C. for 4 hours. A sodium hydroxide aqueous solution was added to the reaction solution to adjust the pH to 10, and the precipitated insoluble matter was removed by filtration using Celite. The filtrate on celite was washed with ethyl acetate. The filtrate was extracted with ethyl acetate, and the organic layer was washed with 20% aqueous sodium hydroxide solution and saturated brine, and dried over anhydrous magnesium sulfate. The residue obtained by distilling off the solvent under reduced pressure was purified by silica gel column chromatography (developing solvent; hexane: ethyl acetate = 4: 1) to obtain 0.930 g (yield 99%) of the title compound. Manufactured.
¹ H-NMR (CDCl ₃ , ppm) δ 3.93 (2H, broadcast-s), 6.99-7.04 (1H, m), 7.11 (1H, t, J = 7.8 Hz), 7 .47-7.49 (1H, m), 7.91 (1H, s), 8.14 (1H, s), 8.28 (1H, d, J = 14.6 Hz).

<1-6>
Preparation of N- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -2-fluoro-3- (methylamino) benzamide

3-amino-N- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -2-fluorobenzamide (0.930 g, 1.71 mmol) was added to 5 ml of concentrated sulfuric acid. In addition, 10 ml of 37% aqueous formaldehyde solution was added dropwise at 40 ° C. The reaction solution was poured into ice water, adjusted to pH 10 with an aqueous sodium hydroxide solution, and then extracted with ethyl acetate. The organic layer was washed with 20% aqueous sodium hydroxide solution and saturated brine, and then dried over anhydrous magnesium sulfate. The residue obtained by evaporating the solvent under reduced pressure was purified by silica gel column chromatography (developing solvent; hexane: ethyl acetate = 8: 1) to obtain 0.690 g (yield 72%) of the title compound. Manufactured.
¹ H-NMR (CDCl ₃ , ppm) δ 2.94 (3H, s), 4.14 (1H, broadcast-s), 6.88-6.93 (1H, m), 7.18 (1H, t , J = 7.8 Hz), 7.37-7.41 (1H, m), 7.90 (1H, s), 8.13 (1H, s), 8.27 (1H, d, J = 14). .6 Hz).

[1-7]
N- (2-Bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -2-fluoro-3- (N-methylbenzamido) benzamide (Compound No. 7-1574) Manufacturing

N- (2-Bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -2-fluoro-3- (methylamino) benzamide 1.54 g (2.75 mmol), pyridine 0.45 g (3.30 mmol) of benzoyl chloride was added to 5 ml of a THF solution of 0.330 g (4.13 mmol), and the mixture was stirred at 60 ° C. for 5 hours. Water and ethyl acetate were added to the reaction solution, and the organic layer was washed with 1M hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated brine, and then dried over anhydrous magnesium sulfate. The residue obtained by distilling off the solvent under reduced pressure was purified by silica gel column chromatography (developing solvent; hexane: ethyl acetate = 8: 1), and the resulting solid was washed with IPE to give the title compound. 1.45 g (80% yield) was produced.
¹ H-NMR (CDCl ₃ , ppm) δ3.50 (3H, s), 6.99-7.33 (6H, m), 7.43-7.45 (1H, m), 7.90 (1H , S), 7.97-8.06 (2H, m), 8.13 (1H, s).

<Example 2>
Preparation of 2-chloro-N- (3- (2,6-dibromo-4- (perfluoropropan-2-yl) phenylcarbamoyl) -2-fluorophenyl) nicotinamide (Compound No. 6-1140)

<2-1>
Production of 4- (perfluoropropan-2-yl) aniline

100 g (1.02 mol) of aniline, 230 g (1.12 mol) of 85% sodium hydrosulfite and 35.1 g (0.100 mol) of tetrabutylammonium hydrogen sulfate were charged into a mixed solution of 1500 ml of t-butyl methyl ether and 1500 ml of water. Then, 94.7 g (1.12 mol) of sodium bicarbonate was added. 350 g (1.12 mol) of heptafluoroisopropyl iodide was added dropwise at room temperature, and the mixture was stirred at room temperature for 6 hours. After separation, the organic layer was washed with 1M hydrochloric acid, water, and a saturated aqueous sodium hydrogen carbonate solution, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and 500 ml of ethyl acetate was charged. 4M hydrogen chloride / ethyl acetate solution (255 g, 1.02 mol) was added dropwise, and the mixture was stirred at room temperature for 30 minutes and at 5 ° C. for 1 hour. The precipitated solid was separated by filtration, and the solid was charged into 1000 ml of ethyl acetate, and 1000 ml of a saturated aqueous sodium hydrogen carbonate solution was added at 20 ° C. or lower to adjust the pH to 8-9, followed by liquid separation. The organic layer was dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to produce 188 g (yield 71%) of the title compound.
¹ H-NMR (CDCl ₃ , ppm) δ 3.92 (2H, broadcast-s), 6.69-6.74 (2H, m), 7.35 (2H, d, J = 9.3 Hz).

<2-2>
Production of 2,6-dibromo-4- (perfluoropropan-2-yl) aniline

216 g (0.802 mol) of 4- (perfluoropropan-2-yl) aniline was charged into 863 ml of DMF and cooled to 5 ° C. 285 g (1.60 mol) of N-bromosuccinimide was charged in portions over 1 hour. After stirring at room temperature for 1 hour, the mixture was stirred at 37 ° C. for 2 hours. After discharging into 2000 ml of water, the mixture was extracted with 2000 ml of ethyl acetate and washed with 1000 ml of saturated saline. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (developing solvent; hexane: ethyl acetate = 20: 1) to produce 304 g (yield 90%) of the title compound.
¹ H-NMR (CDCl ₃ , ppm) δ 4.88 (2H, broadcast-s), 7.59 (2H, s).

<2-3>
Preparation of 2-chloro-N- (2,6-dibromo-4- (perfluoropropan-2-yl) phenyl) -3-nitrobenzamide

The title compound was prepared from 2,6-dibromo-4- (perfluoropropan-2-yl) aniline according to the method of Example 1-3.
¹ H-NMR (CDCl ₃ , ppm) δ 7.58 (1H, t, J = 7.8 Hz), 7.66 (1H, broadcast-s), 7.90 (2H, s), 7.93 (1H , Dd, J = 1.5, 7.8 Hz), 7.98 (1H, d, J = 7.8 Hz).

<2-4>
Preparation of N- (2,6-dibromo-4- (perfluoropropan-2-yl) phenyl) -2-fluoro-3-nitrobenzamide

The title compound was prepared from 2-chloro-N- (2,6-dibromo-4- (perfluoropropan-2-yl) phenyl) -3-nitrobenzamide according to the method of Example 1-4.
¹ H-NMR (CDCl ₃ , ppm) δ 7.51-7.55 (1H, m), 7.90 (2H, s), 8.16 (1H, d, J = 11.7 Hz), 8.27 −8.31 (1H, m), 8.48 (1H, t, J = 6.3 Hz).

<2-5>
Preparation of 3-amino-N- (2,6-dibromo-4- (perfluoropropan-2-yl) phenyl) -2-fluorobenzamide

The title compound was prepared from N- (2,6-dibromo-4- (perfluoropropan-2-yl) phenyl) -2-fluoro-3-nitrobenzamide according to the method of Example 1-5.
¹ H-NMR (CDCl ₃ , ppm) δ 3.93 (2H, broadcast-s), 6.99-7.04 (1H, m), 7.11 (1H, t, J = 7.8 Hz), 7 .47-7.49 (1H, m), 7.91 (1H, s), 8.14 (1H, s), 8.28 (1H, d, J = 14.6 Hz).

<2-6>
Preparation of 2-chloro-N- (3- (2,6-dibromo-4- (perfluoropropan-2-yl) phenylcarbamoyl) -2-fluorophenyl) nicotinamide (Compound No. 6-1140)

According to the method of Example 1-7, from 3-amino-N- (2,6-dibromo-4- (perfluoropropan-2-yl) phenyl) -2-fluorobenzamide and 2-chloronicotinic acid chloride The title compound was prepared.
¹ H-NMR (CDCl ₃ , ppm) δ 7.40-7.49 (2H, m), 7.89 (2H, s), 7.94-7.96 (1H, m), 8.13 (1H , D, J = 12.7 Hz), 8.32-8.34 (1H, m), 8.57-8.59 (1H, m), 8.67-8.71 (1H, m), 8 .75 (1H, broadcast-s).

<Example 3>
Preparation of 3-benzamido-2-fluoro-N- (4- (perfluoropropan-2-yl) -2,6-bis (trifluoromethyl) phenyl) benzamide (Compound No. 6-2110)

<3-1>
Production of 2,6-diiodo-4- (perfluoropropan-2-yl) aniline

To 50 ml of ethanol solution of 5.74 g (22.0 mmol) of 4- (perfluoropropan-2-yl) aniline obtained in 2-1 of Example 2, 2.16 g (22.0 mmol) of concentrated sulfuric acid was added at 5 ° C. added. The temperature of the reaction solution was raised to room temperature, 10.0 g (44.0 mmol) of N-iodosuccinimide was added, and the mixture was stirred for 3 hours. The reaction solution was poured into a saturated aqueous sodium hydrogen carbonate solution to neutralize. The precipitated crystals were filtered, washed with water and dried to produce 9.00 g (yield 80%) of the title compound.
¹ H-NMR (CDCl ₃ , ppm) δ 4.95 (2H, broadcast-s), 7.79 (2H, s).

<3-2>
Preparation of 2-chloro-N- (2,6-diiodo-4- (perfluoropropan-2-yl) phenyl) -3-nitrobenzamide

To a solution of 2,6-diiodo-4- (perfluoropropan-2-yl) aniline 40.0 g (78.0 mmol) in DMI 100 ml, 2-chloro-3-nitrobenzoyl chloride 20.6 g (94.0 mmol) And stirred at 135 ° C. for 3 hours. After cooling to room temperature, the reaction solution was poured into 1000 ml of water. After adding 1000 ml of ethyl acetate and extracting, the organic layer was washed with water and dried over anhydrous magnesium sulfate. The residue obtained by distilling off the solvent under reduced pressure was washed with hexane to produce 56.2 g (yield 99%) of the title compound.
¹ H-NMR (CDCl ₃ , ppm) δ 7.58 (1H, t, J = 8.3 Hz), 7.70 (1H, d, J = 3.4 Hz), 7.93 (1H, dd, J = 1.5, 6.3 Hz), 8.08-8.10 (1H, m), 8.13 (2H, s).

<3-3>
Preparation of N- (2,6-diiodo-4- (perfluoropropan-2-yl) phenyl) -2-fluoro-3-nitrobenzamide

The title compound was prepared from 2-chloro-N- (2,6-diiodo-4- (perfluoropropan-2-yl) phenyl) -3-nitrobenzamide according to the method of Example 1-4.
1H-NMR (CDCl3, ppm) δ 7.52-7.55 (1H, m), 8.12-8.18 (3H, m), 8.29-8.32 (1H, m), 8.48 −8.51 (1H, m).

<3-4>
Preparation of 3-amino-N- (2,6-diiodo-4- (perfluoropropan-2-yl) phenyl) -2-fluorobenzamide

The title compound was prepared from N- (2,6-diiodo-4- (perfluoropropan-2-yl) phenyl) -2-fluoro-3-nitrobenzamide according to the method of Example 1-5.
¹ H-NMR (CDCl ₃ , ppm) δ 3.93 (2H, broadcast-s), 6.99-7.04 (1H, m), 7.08 (1H, t, J = 7.8 Hz), 7 .39-7.43 (1H, m), 8.10 (2H, s), 8.72 (1H, d, J = 11.2 Hz).

<3-5>
Preparation of 3-benzamide-N- (2,6-diiodo-4- (perfluoropropan-2-yl) phenyl) -2-fluorobenzamide (Compound No. 6-1260)

The title compound was prepared from 3-amino-N- (2,6-diiodo-4- (perfluoropropan-2-yl) phenyl) -2-fluorobenzamide according to the method of Example 1-7.
¹ H-NMR (CDCl ₃ , ppm) δ 7.39 (1H, t, J = 7.8 Hz), 7.52-7.57 (4H, m), 7.60-7.63 (2H, m) , 7.93-7.94 (4H, m), 8.70 (1H, t, J = 6.3 Hz).

<3-6>
Preparation of 3-benzamido-2-fluoro-N- (4- (perfluoropropan-2-yl) -2,6-bis (trifluoromethyl) phenyl) benzamide (Compound No. 6-2110)

3-benzamide-N- (2,6-diiodo-4- (perfluoropropan-2-yl) phenyl) -2-fluorobenzamide 1.95 g (2.59 mmol), copper iodide 0.10 g (0.520 mmol) ), 50 ml of a DMF solution of 1.24 g (6.48 mmol) of methyl fluorosulfonyldifluoroacetate was stirred at 100 ° C. for 6 hours. The reaction mixture was cooled to room temperature, 10 ml of water and 100 ml of ethyl acetate were added, and the mixture was filtered through celite. The organic layer of the filtrate was washed with water and a saturated aqueous sodium hydrogen carbonate solution and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (developing solvent; hexane: ethyl acetate = 1: 1), and the resulting solid was washed with hexane to give the title compound 0. 840 g (51% yield) was produced.
¹ H-NMR (CDCl ₃ , ppm) δ 7.36-7.40 (1H, m), 7.53-7.64 (3H, m), 7.84-7.97 (1H, m), 7 .92-7.94 (2H, m), 8.04-8.07 (1H, m), 8.08-8.13 (1H, m), 8.20 (2H, s), 8.68 -8.72 (1H, m).

<Example 4>
Production of N- (2,6-dibromo-4- (perfluorobutan-2-yl) phenyl) -2-fluoro-3- (N-methylbenzamide) benzamide (Compound No. 7-1182)

<4-1>
Preparation of 4- (perfluorobutan-2-yl) aniline

Using a light-shielded reaction vessel, aniline 4.90 g (52.6 mmol), 85% sodium hydrosulfite 10.1 g (58.0 mmol), tetrabutylammonium hydrogen sulfate 1.90 g (5.77 mmol) -A mixed solution of 150 ml of butyl methyl ether and 150 ml of water was charged, and 4.84 g (57.6 mmol) of sodium hydrogen carbonate was added. 20.0 g (57.8 mmol) of nonafluoro-s-butyl iodide was added dropwise at room temperature, and the mixture was stirred at room temperature for 5 hours. The organic phase was separated and washed twice with a 2 mol / L hydrochloric acid aqueous solution, and then washed with a saturated saline solution, a sodium bicarbonate aqueous solution and a saturated saline solution. The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure to produce 8.32 g (yield 51%) of the title compound.
¹ H-NMR (CDCl ₃ , ppm) δ 3.92 (2H, broadcast-s), 6.72 (2H, d, J = 8.8 Hz), 7.34 (2H, d, J = 8.8 Hz) .

<4-2>
Production of 2,6-dibromo-4- (perfluorobutan-2-yl) aniline

The title compound was prepared from 4- (perfluorobutan-2-yl) aniline according to the method of Example 2-2.
¹ H-NMR (CDCl ₃ , ppm) δ 4.89 (2H, broadcast-s), 7.57 (2H, s).

<4-3>
Preparation of 2-chloro-N- (2,6-dibromo-4- (perfluorobutan-2-yl) phenyl) -3-nitrobenzamide

In 27 ml of DMI, 9.90 g (21.1 mmol) of 2,6-dibromo-4- (perfluorobutan-2-yl) aniline and 4.60 g (20.9 g) of 2-chloro-3-nitrobenzoyl chloride mmol) and stirred at 140 ° C. for 4 hours. Water and ethyl acetate were added to the reaction solution, the organic phase was extracted, washed with 1 mol / L aqueous sodium hydroxide solution and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (developing solvent; hexane: ethyl acetate = 20: 1 → 10: 1 → 5: 1 → 3: 1) to give 5.44 g (yield) of the title compound. 40%).
¹ H-NMR (CDCl ₃ , ppm) δ 7.52-7.61 (2H, m), 7.89 (2H, s), 7.94 (1H, dd, J = 1.5, 8.3 Hz) , 7.9 (1H, d, J = 7.8 Hz).

<4-4>
Preparation of N- (2,6-dibromo-4- (perfluorobutan-2-yl) phenyl) -2-fluoro-3-nitrobenzamide

To 108 ml of DMSO, 5.44 g (8.34 mmol) of 2-chloro-N- (2,6-dibromo-4- (perfluorobutan-2-yl) phenyl) -3-nitrobenzamide, potassium fluoride (spray-dried product) 4.90 g (84.3 mmol) was added, and the mixture was stirred at 145 ° C. for 2 hours. The reaction solution was poured into ice water to precipitate crystals, and the obtained crystals were filtered and washed with hexane. The obtained crystals were purified by silica gel column chromatography (developing solvent; hexane: ethyl acetate = 5: 1) to produce 2.42 g (yield 46%) of the title compound.
¹ H-NMR (CDCl ₃ , ppm) δ 7.53-7.54 (1H, m), 7.89 (2H, s), 8.17 (1H, d, J = 12.2 Hz), 8.29 -8.30 (1H, m), 8.48-8.49 (1H, m).

<4-5>
Preparation of 3-amino-N- (2,6-dibromo-4- (perfluorobutan-2-yl) phenyl) -2-fluorobenzamide

The title compound was prepared from N- (2,6-dibromo-4- (perfluorobutan-2-yl) phenyl) -2-fluoro-3-nitrobenzamide according to the method of Example 1-5.
¹ H-NMR (CDCl ₃ , ppm) δ 3.92 (2H, broadcast-s), 6.99-7.04 (1H, m), 7.11-7.12 (1H, m), 7.48 -7.52 (1H, m), 7.86 (2H, s), 8.22 (1H, d, J = 14.1 Hz).

<4-6>
Preparation of N- (2,6-dibromo-4- (perfluorobutan-2-yl) phenyl) -2-fluoro-3- (methylamino) benzamide

The title compound was prepared from 3-amino-N- (2,6-dibromo-4- (perfluorobutan-2-yl) phenyl) -2-fluorobenzamide according to the method of Example 1-6.
¹ H-NMR (CDCl ₃ , ppm) δ 2.95 (3H, s), 4.14 (1H, broadcast-s), 6.91-6.92 (1H, m), 7.17-7.21 (1H, m), 7.39-7.43 (1H, m), 7.85 (2H, s), 8.21 (1H, d, J = 14.1 Hz).

<4-7>
Production of N- (2,6-dibromo-4- (perfluorobutan-2-yl) phenyl) -2-fluoro-3- (N-methylbenzamide) benzamide (Compound No. 7-1182)

The title compound is prepared from N- (2,6-dibromo-4- (perfluorobutan-2-yl) phenyl) -2-fluoro-3- (methylamino) benzamide according to the method of Example 1-7. did.
¹ H-NMR (CDCl ₃ , ppm) δ 3.51 (3H, s), 7.22-7.44 (7H, m), 7.85 (2H, s), 8.00-8.03 (2H , M).

<Example 5>
N- (2-bromo-6- (perfluoroethyl) -4- (perfluoropropan-2-yl) phenyl) -3- (4-cyanobenzamide) -2-fluorobenzamide (Compound No. 6-5911) Manufacturing

<5-1>
Production of 2- (perfluoroethyl) -4- (perfluoropropan-2-yl) aniline

According to the method of Example 1-1, the title was obtained from 4- (perfluoropropan-2-yl) aniline obtained in Example 2-1 and 1,1,2,2,2-pentafluoroethyl iodide. The compound was prepared.
¹ H-NMR (CDCl ₃ , ppm) δ 4.56 (2H, broadcast-s), 6.79 (1H, d, J = 8.8 Hz), 7.47 (1H, d, J = 8.8 Hz) 7.53 (1H, s).

<5-2>
Preparation of 2-bromo-6- (perfluoroethyl) -4- (perfluoropropan-2-yl) aniline

The title compound was prepared from 2- (perfluoroethyl) -4- (perfluoropropan-2-yl) aniline according to the method 1-2 in Example 1.
¹ H-NMR (CDCl ₃ , ppm) δ 5.14 (2H, broadcast-s), 7.58 (1H, s), 7.81 (1H, s).

<5-3>
Preparation of N- (2-bromo-6- (perfluoroethyl) -4- (perfluoropropan-2-yl) phenyl) -2-chloro-3-nitrobenzamide

The title compound was prepared from 2-bromo-6- (perfluoroethyl) -4- (perfluoropropan-2-yl) aniline according to the method of Example 4-4-3.
¹ H-NMR (CDCl ₃ , ppm) δ 7.56-7.61 (1H, m), 7.73 (1H, s), 7.88 (1H, d, J = 1.5 Hz), 7.92 -7.98 (2H, m), 8.21 (1H, s).

<5-4>
Preparation of N- (2-bromo-6- (perfluoroethyl) -4- (perfluoropropan-2-yl) phenyl) -2-fluoro-3-nitrobenzamide

According to the method of Example 1-4, from N- (2-bromo-6- (perfluoroethyl) -4- (perfluoropropan-2-yl) phenyl) -2-chloro-3-nitrobenzamide The compound was prepared.
APCI-MS m / z (M + 1): 626

<5-5>
Preparation of 3-amino-N- (2-bromo-6- (perfluoroethyl) -4- (perfluoropropan-2-yl) phenyl) -2-fluorobenzamide

According to the method of Example 1-5, from N- (2-bromo-6- (perfluoroethyl) -4- (perfluoropropan-2-yl) phenyl) -2-fluoro-3-nitrobenzamide The compound was prepared.
¹ H-NMR (CDCl ₃ , ppm) δ 3.92 (2H, broadcast-s), 6.99-7.04 (1H, m), 7.05-7.18 (1H, m), 7.46 -7.51 (1H, m), 7.85 (1H, broadcast-s), 8.17 (1H, broadcast-s), 8.34 (1H, d, J = 15.1 Hz).

<5-6>
N- (2-bromo-6- (perfluoroethyl) -4- (perfluoropropan-2-yl) phenyl) -3- (4-cyanobenzamide) -2-fluorobenzamide (Compound No. 6-5911) Manufacturing

According to the method of Example 1 1-7, 3-amino-N- (2-bromo-6- (perfluoroethyl) -4- (perfluoropropan-2-yl) phenyl) -2-fluorobenzamide and 4 The title compound was prepared from cyanobenzoyl chloride.
¹ H-NMR (CDCl ₃ , ppm) δ 7.41 (1H, t, J = 8.3 Hz), 7.84-7.87 (3H, m), 7.91-7.95 (1H, m) , 8.03-8.05 (2H, m), 8.10 (1H, broadcast-s), 8.17-8.20 (2H, m), 8.63-8.67 (1H, m) .

<Example 6>
Production of N- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -6- (N-methylbenzamido) picolinamide (Compound No. 17-1103)

<6-1>
Preparation of N- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -6-chloropicolinamide

2-Chloropyridine-6-carboxylic acid chloride prepared from 2-chloropyridine-6-carboxylic acid and thionyl chloride according to method 1-3 of Example 1 and 2 obtained in 1-2 of Example 1 The title compound was prepared from -bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) aniline.
¹ H-NMR (CDCl ₃ , ppm) δ 7.59 (1H, d, J = 7.3 Hz), 7.90-7.93 (2H, m), 8.14 (1H, s), 8.20 -8.24 (1H, m), 9.60 (1H, s).

<6-2>
Preparation of N- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -6- (methylamino) picolinamide

5 ml of 1,4-dioxane solution of 0.100 g (0.180 mmol) of N- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -6-chloropicolinamide To the mixture, 0.00600 g (0.0360 mmol) of copper sulfate and 0.140 g (1.80 mmol) of a 40% aqueous methylamine solution were added, and the mixture was stirred at an oil bath temperature of 80 ° C. for 3 hours under sealed conditions. The reaction solution was returned to room temperature and opened, water and ethyl acetate were added, and the organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by silica gel column chromatography (developing solvent; hexane: ethyl acetate = 2: 1) to produce 0.0700 g (yield 69%) of the title compound. .
¹ H-NMR (CDCl ₃ , ppm) δ 2.64 (3H, s), 3.79 (1H, broadcast-s), 7.56-7.60 (1H, m), 7.87-7.93 (2H, m), 8.14-8.15 (1H, m), 8.20-8.23 (1H, m), 9.60 (1H, s).

<6-3>
Production of N- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -6- (N-methylbenzamido) picolinamide (Compound No. 17-1103)

According to the method of Example 1-7, from N- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -6- (methylamino) picolinamide The compound was prepared.
¹ H-NMR (CDCl ₃ , ppm) δ 3.65 (3H, s), 7.28-7.41 (6H, m), 7.77 (1H, t, J = 7.8 Hz), 7.91 (1H, s), 8.00-8.02 (1H, m), 8.14 (1H, s), 9.39 (1H, s).

<Example 7>
N- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -2- (2-fluoro-N-methylbenzamido) thiazole-4-carboxamide (Compound No. 27 -628)

<7-1>
Preparation of 2-aminothiazole-4-carboxylic acid

1.40 g (46.5 mmol) of sodium hydroxide was added to 40 ml of an aqueous solution of 4.00 g (23.2 mmol) of ethyl 2-aminothiazole-4-carboxylate, and the mixture was stirred at room temperature for 5 hours. Concentrated hydrochloric acid was added to the reaction solution to adjust the pH to 1, and the precipitated crystals were collected by filtration to produce 2.84 g (yield 85%) of the title compound.
¹ H-NMR (CDCl ₃ , ppm) δ 7.18 (2H, broadcast-s), 7.38 (1H, s).
The carboxylic acid proton is not detected.

<7-2>
Preparation of 2-chlorothiazole-4-carboxylic acid

50 ml of concentrated hydrochloric acid was added to 30 ml of 1,4-dioxane solution of 2.84 g (19.7 mmol) of 2-aminothiazole-4-carboxylic acid and cooled to 0 ° C., and 2.04 g (29.6 mmol) of sodium nitrite was added. 10 ml of an aqueous solution was added dropwise at 0 to 5 ° C. After stirring the reaction solution at 0 ° C. for 2 hours, 2.93 g (29.6 mmol) of copper chloride was charged in portions, and the reaction solution was returned to room temperature and stirred for 8 hours. Water and ethyl acetate were added to the reaction mixture, and the mixture was extracted 4 times with ethyl acetate. The organic layer was washed with saturated brine and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to produce 1.77 g (yield 55%) of the title compound.
¹ H-NMR (DMSO-d ₆ , ppm) δ 8.41 (1H, s).
The carboxylic acid proton is not detected.

<7-3>
Preparation of N- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -2-chlorothiazole-4-carboxamide

2-Chlorothiazole-4-carbonyl chloride prepared from 2-chlorothiazole-4-carboxylic acid and thionyl chloride according to the method of 4-3 of Example 4 and 2- The title compound was prepared from bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) aniline.
¹ H-NMR (CDCl ₃ , ppm) δ 7.91 (1H, s), 8.13 (1H, s), 8.19 (1H, s), 8.82 (1H, s).

<7-4>
Preparation of N- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -2- (methylamino) thiazole-4-carboxamide

According to the method of Example 6-2, from N- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -2-chlorothiazole-4-carboxamide The compound was prepared.
¹ H-NMR (CDCl ₃ , ppm) δ 3.03 (3H, s), 5.11-5.12 (1H, m), 7.50 (1H, s), 7.88 (1H, s), 8.11 (1H, s), 8.99 (1H, s).

<7-5>
N- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -2- (2-fluoro-N-methylbenzamido) thiazole-4-carboxamide (Compound No. 27 -628)

According to the method of Example 1 1-7, N- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -2- (methylamino) thiazole-4- The title compound was prepared from carboxamide and 2-fluorobenzoyl chloride.
¹ H-NMR (CDCl ₃ , ppm) δ 3.67 (3H, s), 699-7.24 (1H, m), 7.29-7.35 (1H, m), 7.52-7 .59 (2H, m), 7.90 (1H, s), 8.06 (1H, s), 8.14 (1H, s), 9.08 (1H, s).

<Example 8>
2,2,2-Trichloroethyl 2-fluoro-3- (2-iodo-4- (perfluorobutan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl (methyl) carbamate (Compound No. 12 -864)

<8-1>
Production of 4- (perfluorobutan-2-yl) -2- (trifluoromethyl) aniline

The title compound was produced from 2- (trifluoromethyl) aniline and nonafluoro-s-butyl iodide under the light-shielding reaction conditions according to the method 1-1 in Example 1.
¹ H-NMR (CDCl ₃ , ppm) δ 4.49 (2H, broadcast-s), 6.81 (1H, d, J = 8.8 Hz), 7.47 (1H, d, J = 8.8 Hz) , 7.61 (1H, s).

<8-2>
Preparation of 2-iodo-4- (perfluorobutan-2-yl) -6- (trifluoromethyl) aniline

To 100 mL of ethanol was added 17.0 g (44.8 mmol) of 4- (perfluorobutan-2-yl) -2- (trifluoromethyl) aniline, and 5.28 g (53.8 g) of concentrated sulfuric acid under ice cooling. mmol) and 12.6 g (55.8 mmol) of N-iodosuccinimide were added, and the mixture was stirred at room temperature for 1 hour 30 minutes and at 40 ° C. for 4 hours. A 4M aqueous sodium hydroxide solution was added to the reaction solution to neutralize the reaction solution, and then ethyl acetate was added to extract the organic phase. The organic phase was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (developing solvent; hexane: ethyl acetate = 10: 1) to produce 14.6 g (yield 65%) of the title compound.
¹ H-NMR (CDCl ₃ , ppm) δ 5.04 (2H, broadcast-s), 7.62 (1H, s), 7.97 (1H, s).

<8-3>
Preparation of 2-chloro-N- (2-iodo-4- (perfluorobutan-2-yl) -6- (trifluoromethyl) phenyl) -3-nitrobenzamide

The title compound was prepared from 2-iodo-4- (perfluorobutan-2-yl) -6- (trifluoromethyl) aniline according to the method of Example 4-4-3.
¹ H-NMR (CDCl ₃ , ppm) δ 7.60-7.61 (1H, m), 7.77 (1H, s), 7.89-7.96 (2H, m), 8.03-8 .04 (1H, m), 8.38 (1H, s).

<8-4>
Preparation of 2-fluoro-N- (2-iodo-4- (perfluorobutan-2-yl) -6- (trifluoromethyl) phenyl) -3-nitrobenzamide

According to the method of Example 1-4, from 2-chloro-N- (2-iodo-4- (perfluorobutan-2-yl) -6- (trifluoromethyl) phenyl) -3-nitrobenzamide The compound was prepared.
¹ H-NMR (CDCl ₃ , ppm) δ 7.53-7.54 (1H, m), 7.95 (1H, s), 8.24-8.32 (2H, m), 8.36 (1H , S), 8.44-8.48 (1H, m).

<8-5>
Preparation of 3-amino-2-fluoro-N- (2-iodo-4- (perfluorobutan-2-yl) -6- (trifluoromethyl) phenyl) benzamide

According to the method of Example 1-5, from 2-fluoro-N- (2-iodo-4- (perfluorobutan-2-yl) -6- (trifluoromethyl) phenyl) -3-nitrobenzamide The compound was prepared.
¹ H-NMR (CDCl ₃ , ppm) δ 3.93 (2H, broadcast-s), 7.02-7.03 (1H, m), 7.11-7.13 (1H, m), 7.47 -7.51 (1H, m), 7.92 (1H, s), 8.31-8.34 (2H, m).

<8-6>
Preparation of 2-fluoro-N- (2-iodo-4- (perfluorobutan-2-yl) -6- (trifluoromethyl) phenyl) -3- (methylamino) benzamide

In accordance with the method of Example 1-6, from 3-amino-2-fluoro-N- (2-iodo-4- (perfluorobutan-2-yl) -6- (trifluoromethyl) phenyl) benzamide The compound was prepared.
¹ H-NMR (CDCl ₃ , ppm) δ 2.95-2.96 (3H, m), 4.15 (1H, broadcast-s), 6.91-6.93 (1H, m), 7.19 -7.20 (1H, m), 7.38-7.42 (1H, m), 7.92 (1H, s), 8.32 (1H, d, J = 14.1 Hz), 8.34 (1H, s).

<8-7>
2,2,2-Trichloroethyl 2-fluoro-3- (2-iodo-4- (perfluorobutan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl (methyl) carbamate (Compound No. 12 -864)

According to the method of Example 1-7, 2-fluoro-N- (2-iodo-4- (perfluorobutan-2-yl) -6- (trifluoromethyl) phenyl) -3- (methylamino) The title compound was prepared from benzamide and 2,2,2-trichloroethoxycarbonyl chloride.
¹ H-NMR (CDCl ₃ , ppm) δ 3.40 (3H, s), 4.74 (2H, broadcast-s), 7.37 (1H, t, J = 7.8 Hz), 7.52-7 .58 (1H, m), 7.93 (1H, s), 8.12-8.15 (1H, m), 8.28-8.34 (2H, m).

<Example 9>
N- (2-Chloro-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -4-cyano-3- (4-cyano-N-methylbenzamido) benzamide (Compound No. 2 -491)

<9-1>
Preparation of 2-chloro-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) aniline

According to the method 1-2 of Example 1, from 4- (perfluoropropan-2-yl) -2- (trifluoromethyl) aniline obtained in 1-1 of Example 1 and N-chlorosuccinimide The title compound was prepared.
¹ H-NMR (CDCl ₃ , ppm) δ 4.97 (2H, broadcast-s), 7.57 (1H, s), 7.64 (1H, s).

<9-2>
Preparation of N- (2-chloro-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -4-iodo-3-nitrobenzamide

4-Iodo-3-nitrobenzoyl chloride prepared from 4-iodo-3-nitrobenzoic acid and thionyl chloride according to the method of Example 1-3 1-3 and 2-chloro-4- (perfluoropropane-2- The title compound was prepared from yl) -6- (trifluoromethyl) aniline.
¹ H-NMR (CDCl ₃ , ppm) δ 7.52-7.81 (2H, m), 7.89 (1H, s), 8.00 (1H, s), 8.25 (1H, d, J = 8.3 Hz), 8.38 (1H, d, J = 1.9 Hz).

<9-3>
Preparation of 3-amino-N- (2-chloro-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -4-iodobenzamide

According to the method of Example 1-5, from N- (2-chloro-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -4-iodo-3-nitrobenzamide The compound was prepared.
¹ H-NMR (CDCl ₃ , ppm) δ 4.35 (2H, s), 6.92 (1H, dd, J = 1.9, 8.3 Hz), 7.29 (1H, d, J = 1. 9 Hz), 7.60 (1 H, s), 7.79 (1 H, d, J = 8.3 Hz), 7.86 (1 H, s), 7.97 (1 H, s).

<9-4>
Preparation of N- (2-chloro-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -4-iodo-3- (methylamino) benzamide

According to the method of Example 1-6, from 3-amino-N- (2-chloro-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -4-iodobenzamide The compound was prepared.
¹ H-NMR (CDCl ₃ , ppm) δ 2.97 (3H, s), 4.46 (1H, broadcast-s), 6.89 (1H, dd, J = 1.9, 8.3 Hz), 7 .07 (1H, d, J = 1.9 Hz), 7.65 (1H, s), 7.80 (1H, d, J = 8.3 Hz), 7.86 (1H, s), 7.97 (1H, s).

<9-5>
Preparation of N- (2-chloro-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -4-cyano-3- (methylamino) benzamide

0.350 g (0.560 mmol) of N- (2-chloro-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -4-iodo-3- (methylamino) benzamide in 10 mL of DMF ), 0.200 g (2.25 mmol) of copper (I) cyanide was added, and the mixture was stirred at 140 ° C. for 1 hour 30 minutes. After quenching the reaction by pouring a saturated aqueous sodium thiosulfate solution into the reaction solution, the organic layer was separated with ethyl acetate and washed with saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (developing solvent; hexane: ethyl acetate = 5: 1 → 3: 1) to produce 0.250 g (yield 86%) of the title compound.
¹ H-NMR (CDCl ₃ , ppm) δ 3.01 (1/2 * 3H, s), 3.03 (1/2 * 3H, s), 4.89 (1/2 * 1H, s), 4 .90 (1/2 * 1H, s), 7.80 (1H, dd, J = 1.5, 8.3 Hz), 7.21-7.22 (1H, m), 7.54 (1H, d, J = 8.3 Hz), 7.67 (1H, s), 7.88 (1H, s), 7.99 (1H, s).

<9-6>
N- (2-Chloro-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -4-cyano-3- (4-cyano-N-methylbenzamido) benzamide (Compound No. 2 -491)

According to the method of Example 1 1-7, N- (2-chloro-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -4-cyano-3- (methylamino) The title compound was prepared from benzamide and 4-cyanobenzoyl chloride.
¹ H-NMR (CDCl ₃ , ppm) δ 3.81 (3H, broadcast-s), 7.52-7.84 (8H, m), 7.89 (1H, s), 8.00 (1H, s ).

<Example 10>
N- (3- (2-Bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) -6-cyano-2-fluorophenyl) -6-chloronicotinamide (compound No. 1-1968)

<10-1>
Preparation of N- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -4-cyano-2,3-difluorobenzamide

1 drop of DMF and 0.470 ml (5.51 mmol) of oxalyl chloride were added to 10 ml of a dichloromethane solution of 0.840 g (4.59 mmol) of 4-cyano-2,3-difluorobenzoic acid, followed by stirring at room temperature for 1 hour. 4-Cyano-2,3-difluorobenzoyl chloride obtained by distilling off the solvent under reduced pressure was converted to 2-bromo-4- (perfluoropropan-2-yl) -6 obtained in 1-2 of Example 1. -(Trifluoromethyl) aniline was added to 5 ml of a DMI solution of 1.56 g (3.83 mmol) and stirred at 130 ° C. for 5 hours. Water and ethyl acetate were added to the reaction solution, and the organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and then dried over anhydrous magnesium sulfate. The residue obtained by distilling off the solvent under reduced pressure was purified by silica gel column chromatography (developing solvent; hexane: ethyl acetate = 1: 0 → 10: 1) to give 0.58 g of the title compound (yield 27%). ) Was manufactured.
¹ H-NMR (CDCl ₃ , ppm) δ 7.52-7.62 (1H, m), 7.92-7.94 (1H, m), 8.02-8.06 (1H, m), 8 .13-8.16 (2H, m).

<10-2>
Preparation of 3-amino-N- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -4-cyano-2-fluorobenzamide

49.0 mg of ammonium carbonate was added to 5 ml of a DMSO solution of N- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -4-cyano-2,3-difluorobenzamide. In addition, the mixture was stirred at 100 ° C. for 5 hours. Water and ethyl acetate were added to the reaction solution, and the organic layer was washed with water and then dried over anhydrous magnesium sulfate. The residue obtained by distilling off the solvent under reduced pressure was purified by silica gel column chromatography (developing solvent; hexane: ethyl acetate = 8: 1 → 4: 1) to give 0.30 g of the title compound (51% yield) ) Was manufactured.
¹ H-NMR (CDCl ₃ , ppm) δ 4.71 (2H, broadcast-s), 7.35-7.39 (1H, m), 7.40-7.44 (1H, m), 7.92 (1H, s), 8.12-8.15 (2H, m).

<10-3>
N- (3- (2-Bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) -6-cyano-2-fluorophenyl) -6-chloronicotinamide (compound No. 1-1968)

0.0500 g (0.0877 mol) of 3-amino-N- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -4-cyano-2-fluorobenzamide To 0.200 ml of the DMI solution, 0.0308 g (0.175 mmol) of 6-chloronicotinoyl chloride was added and stirred at 130 ° C. for 6 hours. Water and ethyl acetate were added to the reaction solution, and the organic layer was washed with 1M hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated brine, and then dried over anhydrous magnesium sulfate. The residue obtained by distilling off the solvent under reduced pressure was purified by silica gel column chromatography (developing solvent; hexane: ethyl acetate = 2: 1) to produce 0.0100 g (yield 16%) of the title compound. .
¹ H-NMR (CDCl ₃ , ppm) δ 7.54 (1H, d, J = 8.8 Hz), 7.72 (1H, d, J = 8.8 Hz), 7.93 (1H, s), 8 .09 (1H, s), 8.17-8.18 (2H, m), 8.27 (1H, dd, J = 2.4 Hz 8.8 Hz), 8.38 (1H, d, J = 10) .8 Hz), 8.98 (1H, d, J = 2.4 Hz).

<Example 11>
Preparation of 3- (4-cyanobenzamide) -N- (2,6-diiodo-4- (perfluorobutan-2-yl) phenyl) benzamide (Compound No. 6-79)

<11-1>
Production of 2,6-diiodo-4- (perfluorobutan-2-yl) aniline

The title compound was produced from 4- (perfluorobutan-2-yl) aniline obtained in 4-1 of Example 4 according to the method of Example 3-1.
¹ H-NMR (CDCl ₃ , ppm) δ 4.95 (2H, broadcast-s), 7.78 (2H, s).

<11-2>
Preparation of N- (2,6-diiodo-4- (perfluorobutan-2-yl) phenyl) -3-nitrobenzamide

The title compound was prepared from 2,6-diiodo-4- (perfluorobutan-2-yl) aniline and 3-nitrobenzoyl chloride according to the method of Example 4-4-3.
¹ H-NMR (CDCl ₃ , ppm) δ 7.74 (1H, t, J = 8.0 Hz), 8.11 (2H, s), 8.42 (1H, d, J = 7.6 Hz), 8 .46 (1H, d, J = 8.4 Hz), 8.90 (1H, d, J = 12.4 Hz), 8.92 (1H, s).

<11-3>
Preparation of 3-amino-N- (2,6-diiodo-4- (perfluorobutan-2-yl) phenyl) benzamide

The title compound was prepared from N- (2,6-diiodo-4- (perfluorobutan-2-yl) phenyl) -3-nitrobenzamide according to the method of Example 1-5.
¹ H-NMR (CDCl ₃ , ppm) δ 5.39 (2H, broadcast-s), 6.89-6.93 (1H, m), 7.29-7.31 (3H, m), 7.68 (1H, s), 8.08 (2H, s).

<11-4>
Preparation of 3- (4-cyanobenzamide) -N- (2,6-diiodo-4- (perfluorobutan-2-yl) phenyl) benzamide (Compound No. 6-79)

The title compound was prepared from 3-amino-N- (2,6-diiodo-4- (perfluorobutan-2-yl) phenyl) benzamide and 4-cyanobenzoyl chloride according to the method of Example 1-7. .
¹ H-NMR (CDCl ₃ , ppm) δ 7.58 (1H, t, J = 8.2 Hz), 7.79-7.83 (3H, m), 7.97 (2H, s), 8.01 (2H, d, J = 8.0 Hz), 8.09 (2H, s), 8.18 (1H, s), 8.29 (1H, s).

<Example 12>
N- (3- (2-Bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethoxy) phenylcarbamoyl) -2-fluorophenyl) -2-chloronicotinamide (Compound No. 6-5908) )Manufacturing of

<12-1>
Preparation of 4- (perfluoropropan-2-yl) -2- (trifluoromethoxy) aniline

The title compound was prepared from 2-trifluoromethoxyaniline according to the method 1-1 of Example 1.
¹ H-NMR (CDCl ₃ , ppm) δ 4.19 (2H, broadcast-s), 6.86 (1H, d, J = 8.8 Hz), 7.30 (1H, d, J = 8.8 Hz) , 7.36 (1H, s).

<12-2>
Preparation of 2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethoxy) aniline

The title compound was prepared from 4- (perfluoropropan-2-yl) -2- (trifluoromethoxy) aniline according to the method 1-2 in Example 1.
¹ H-NMR (CDCl ₃ , ppm) δ 4.65 (2H, broadcast-s), 7.33 (1H, s), 7.71 (1H, s).

<12-3>
Preparation of N- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethoxy) phenyl) -2-chloro-3-nitrobenzamide

The title compound was prepared from 2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethoxy) aniline according to the method of Example 1-3.
¹ H-NMR (CDCl ₃ , ppm) δ 7.49-7.61 (3H, m), 7.80-7.96 (3H, m).

<12-4>
Preparation of N- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethoxy) phenyl) -2-fluoro-3-nitrobenzamide

According to the method of Example 1-4, from N- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethoxy) phenyl) -2-chloro-3-nitrobenzamide The compound was prepared.
¹ H-NMR (CDCl ₃ , ppm) δ 7.53 (1H, t, J = 7.8 Hz), 7.60 (1H, broadcast-s), 7.89 (1H, d, J = 1.5 Hz) , 8.07 (1H, broadcast-d, J = 12.7 Hz), 8.29-8.30 (1H, m), 8.43-8.47 (1H, m).

<12-5>
Preparation of 3-amino-N- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethoxy) phenyl) -2-fluorobenzamide

According to the method of Example 1-5, from N- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethoxy) phenyl) -2-fluoro-3-nitrobenzamide The compound was prepared.
¹ H-NMR (CDCl ₃ , ppm) δ 3.92 (2H, broadcast-s), 6.99-7.04 (1H, m), 7.11 (1H, t, J = 7.8 Hz), 7 .45-7.49 (1H, m), 7.57 (1H, broadcast-s), 7.87 (1H, d, J = 2.0 Hz), 8.14 (1H, d, J = 14. 2 Hz).

<12-6>
N- (3- (2-Bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethoxy) phenylcarbamoyl) -2-fluorophenyl) -2-chloronicotinamide (Compound No. 6-5908) )Manufacturing of

According to the method of Example 1 1-7, 3-amino-N- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethoxy) phenyl) -2-fluorobenzamide and 2 The title compound was prepared from chloronicotinoyl chloride.
¹ H-NMR (CDCl ₃ , ppm) δ 7.39-7.49 (2H, m), 7.59 (1H, s), 7.88-7.94 (2H, m), 8.07 (1H , D, J = 12.2 Hz), 8.31-8.33 (1H, m), 8.57-8.58 (1H, m), 8.60-8.70 (1H, m), 8 74 (1H, broadcast-s).

<Example 13>
Preparation of 3-benzamide-N- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -4-fluorobenzamide (Compound No. 6-3348)

<13-1>
Preparation of N- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -4-fluoro-3-nitrobenzamide

In accordance with the method of Example 1-3, 4-fluoro-3-nitrobenzoyl chloride prepared from 4-fluoro-3-nitrobenzoic acid and thionyl chloride and the 2-amino acid obtained in 1-2 of Example 1 The title compound was prepared from bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) aniline.
¹ H-NMR (CDCl ₃ , ppm) δ 7.47-7.50 (1H, m), 7.92 (2H, d, J = 5.9 Hz), 8.16 (1H, s), 8.23 -8.28 (1H, m), 8.65-8.67 (1H, m).

<13-2>
Preparation of 3-amino-N- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -4-fluorobenzamide

According to the method of Example 1-5, from N- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -4-fluoro-3-nitrobenzamide The compound was prepared.
APCI-MS m / z (M + 1): 546

<13-3>
Preparation of 3-benzamide-N- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -4-fluorobenzamide (Compound No. 6-3348)

According to the method of Example 1-7, from 3-amino-N- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -4-fluorobenzamide The compound was prepared.
¹ H-NMR (CDCl ₃ , ppm) δ 7.29-7.34 (1H, m), 7.53-7.65 (3H, m), 7.80-7.84 (1H, m), 7 90-9.92 (3H, m), 8.14 (1H, broadcast-s), 8.20 (1H, d, J = 2.9 Hz), 8.25 (1H, broadcast-s), 9 .10 (1H, dd, J = 1.9, 7.3 Hz).

<Example 14>
Preparation of 2-chloro-N- (3- (2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) nicotinamide (Compound No. 6-460)

<14-1>
Preparation of 2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) aniline

According to the method of Example 8-8-2, from 4- (perfluoropropan-2-yl) -2- (trifluoromethyl) aniline obtained in 1-1 of Example 1 and N-iodosuccinimide The title compound was prepared.
¹ H-NMR (CDCl ₃ , ppm) δ 5.04 (2H, broadcast-s), 7.64 (1H, s), 7.99 (1H, s).

<14-2>
Preparation of N- (2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -3-nitrobenzamide

The title compound was prepared from 2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) aniline and 3-nitrobenzoyl chloride according to the method of Example 4-4-3.
¹ H-NMR (CDCl ₃ , ppm) δ 7.76-7.80 (2H, m), 7.97 (1H, s), 8.28-8.30 (1H, m), 8.37 (1H , S), 8.49-8.52 (1H, m), 8.78 (1H, s).

<14-3>
Preparation of 3-amino-N- (2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) benzamide

The title compound was prepared from N- (2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -3-nitrobenzamide according to the method of Example 1-5. .
¹ H-NMR (CDCl ₃ , ppm) δ 3.89 (2H, broadcast-s), 6.89-6.92 (1H, m), 7.23-7.32 (3H, m), 7.68 (1H, s), 7.93 (1H, s), 8.34-8.36 (1H, m).

<14-4>
Preparation of 2-chloro-N- (3- (2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenylcarbamoyl) phenyl) nicotinamide (Compound No. 6-460)

According to the method of Example 1-7, 3-amino-N- (2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) benzamide and 2-chloronicotinoyl The title compound was prepared from chloride.
¹ H-NMR (CDCl ₃ , ppm) δ 7.43-7.46 (1H, m), 7.58 (1H, t, J = 7.8 Hz), 7.77 (1H, d, J = 7. 8Hz), 7.91-7.95 (2H, m), 8.01 (1H, s), 8.24 (1H, dd, J = 2.0, 7.8Hz), 8.28 (1H, s), 8.36 (1H, s), 8.41 (1H, s), 8.54-8.56 (1H, m).

<Example 15>
2-Fluoro-3- (4-fluoro-N-methylbenzamide) -N- (2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) benzamide (Compound No. 7 -1733)

<15-1>
Preparation of 2-chloro-N- (2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -3-nitrobenzamide

According to the method of Example 4-4-3, 2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) aniline obtained in 14-1 of Example 14 and 2-chloro The title compound was prepared from -3-nitrobenzoyl chloride.
¹ H-NMR (CDCl ₃ , ppm) δ 7.60 (1H, t, J = 7.8 Hz), 7.76 (1H, s), 7.94 (1H, dd, J = 1.5, 7. 8 Hz), 7.97 (1 H, s), 8.03 (1 H, dd, J = 1.5, 7.8 Hz), 8.39 (1 H, s).

<15-2>
Preparation of 2-fluoro-N- (2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -3-nitrobenzamide

According to the method of Example 1-4, from 2-chloro-N- (2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -3-nitrobenzamide The compound was prepared.
¹ H-NMR (CDCl ₃ , ppm) δ 7.51-7.55 (1H, m), 7.97 (1H, s), 8.23 (1H, d, J = 12.2 Hz), 8.28 -8.32 (1H, m), 8.37 (1H, s), 8.44-8.48 (1H, m).

<15-3>
Preparation of 3-amino-2-fluoro-N- (2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) benzamide

According to the method of Example 1-5, from 2-fluoro-N- (2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -3-nitrobenzamide The compound was prepared.
¹ H-NMR (CDCl ₃ , ppm) δ 3.92 (2H, broadcast-s), 7.02-7.04 (1H, m), 7.11 (1H, t, J = 7.8 Hz), 7 .47-7.52 (1H, m), 7.94 (1H, s), 8.30-8.35 (2H, m).

<15-4>
Preparation of 2-fluoro-N- (2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -3- (methylamino) benzamide

According to the method of Example 1-6, from 3-amino-2-fluoro-N- (2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) benzamide The compound was prepared.
¹ H-NMR (CDCl ₃ , ppm) δ 2.95 (3H, s), 4.15 (1H, broadcast-s), 6.90 (1H, t, J = 8.2 Hz), 7.19 (1H , T, J = 7.8 Hz), 7.40 (1H, t, J = 7.8 Hz), 7.92 (1H, s), 8.30 (1H, s), 8.34 (1H, s) ).

<15-5>
2-Fluoro-3- (4-fluoro-N-methylbenzamide) -N- (2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) benzamide (Compound No. 7 -1733)

According to the method of Example 1-7, 2-fluoro-N- (2-iodo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -3- (methylamino) The title compound was prepared from benzamide and 4-fluorobenzoyl chloride.
¹ H-NMR (CDCl ₃ , ppm) δ3.50 (3H, s), 6.91 (2H, s), 6.93-7.35 (3H, m), 7.46 (1H, t, J = 7.0 Hz), 7.93 (1H, s), 8.01-8.10 (1H, m), 8.13 (1H, broadcast-s), 8.34 (1H, s).

<Example 16>
N- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -2-fluoro-N-methyl-3- (N-methylbenzamido) benzamide (Compound No. 9 -2164)

N- (2-Bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -2-fluoro-3- (N-methyl) obtained in 1-7 of Example 1 Benzamide) 0.00900 g (0.230 mmol) of sodium hydride (60% in oil) was added to 5 ml of a DMF solution of 0.100 g (0.150 mmol) of benzamide and stirred at room temperature for 40 minutes. To the reaction solution, 0.0300 g (0.180 mmol) of methyl iodide was added and stirred at the same temperature for 6 hours. Water and ethyl acetate were added to the reaction solution, and the organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The residue obtained by distilling off the solvent under reduced pressure was purified by silica gel column chromatography (developing solvent; hexane: ethyl acetate = 4: 1) to quantitatively produce the title compound (0.106 g).
¹ H-NMR (CDCl ₃ , ppm) δ 2.18-2.19 (3H, m), 3.48 (3H, s), 7.21-7.25 (4H, m), 7.32-7 .40 (4H, m), 7.92 (1H, s), 8.13 (1H, s).

<Example 17>
N- (2-Bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -3- (4-cyanobenzamide) -N-methylbenzamide (Compound No. 8-289) Manufacturing

<17-1>
Preparation of N- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -3-nitrobenzamide

According to the method of Example 4-4-3, 2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) aniline and 3-nitro obtained in 1-2 of Example 1 The title compound was prepared from benzoyl chloride.
¹ H-NMR (CDCl ₃ , ppm) δ 7.75-7.79 (2H, m), 7.94 (1H, s), 8.17 (1H, d, J = 1.0 Hz), 8.28 (1H, dd, J = 1.5, 7.8 Hz), 8.48-8.51 (1H, m), 8.76-8.77 (1H, m).

<17-2>
Preparation of N- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -N-methyl-3-nitrobenzamide

The title compound was prepared from N- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -3-nitrobenzamide according to the method of Example 16.
¹ H-NMR (CDCl ₃ , ppm) δ 3.28 (1/2 * 3H, s), 3.44 (1/2 * 3H, s), 7.41 (1/2 * 1H, t, J = 7.8 Hz), 7.71-7.76 (2/2 * 1H, m), 7.84 (1/2 * 1H, s), 7.93-7.95 (1/2 * 1H, m) ), 7.98 (1/2 * 1H, s), 8.07-8.09 (2/2 * 1H, m), 8.14-8.16 (1/2 * 1H, m), 8 .19 (1/2 * 1H, s), 8.39-8.41 (1/2 * 1H, m), 8.45-8.46 (1/2 * 1H, m).

<17-3>
Preparation of 3-amino-N- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -N-methylbenzamide

According to the method of Example 1-5, from N- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -N-methyl-3-nitrobenzamide The compound was prepared.
¹ H-NMR (CDCl ₃ , ppm) δ 3.24 (3/4 * 3H, s), 3.37 (1/4 * 3H, s), 3.80 (2H, broadcast-s), 6.47 (1/4 * 1H, d, J = 7.8 Hz), 6.54-6.57 (1/4 * 1H, m), 6.78-6.84 (5/4 * 1H, m), 6.86 (3/4 * 1H, t, J = 2.0 Hz), 6.96 (3/4 * 1H, d, J = 7.8 Hz), 7.23-7.27 (3/4 * 1H, m), 7.79 (1/4 * 1H, s), 7.94 (3/4 * 1H, s), 8.00 (1/4 * 1H, s), 8.15 (3 / 4 * 1H, s).

<17-4>
N- (2-Bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -3- (4-cyanobenzamide) -N-methylbenzamide (Compound No. 8-289) Manufacturing

According to the method 1-7 of Example 1, 3-amino-N- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -N-methylbenzamide and 4- The title compound was prepared from cyanobenzoyl chloride.
¹ H-NMR (CDCl ₃ , ppm) δ 3.26 (2/3 * 3H, s), 3.38 (1/3 * 3H, s), 7.08-7.09 (1/3 * 1H, m), 7.12-7.14 (1/3 * 1H, m), 7.32 (2/3 * 1H, d, J = 7.8 Hz), 7.45-7.49 (3/3) * 1H, m), 7.72-7.76 (9/3 * 1H, m), 7.83 (1/3 * 1H, s), 7.85-7.89 (4/3 * 1H, m), 7.95 (2/3 * 1H, s), 7.98-8.00 (4/3 * 1H, m), 8.04 (2/3 * 1H, d, J = 6.3 Hz) ), 8.16 (2/3 * 1H, s), 8.57 (2/3 * 1H, s).

<Example 18>
Preparation of 3-benzamide-N- (2-bromo-4- (perfluoroethyl) -6- (trifluoromethyl) phenyl) benzamide (Compound No. 6-5913)

<18-1>
Production of 4- (perfluoroethyl) -2- (trifluoromethyl) aniline

Add 13.6 g (33.7 mmol) of 2- (trifluoromethyl) aniline and 40 ml of DMF to 40 ml of an aqueous solution of 7.04 g (40.4 mmol) of 85% sodium hydrosulfite and 3.40 g (40.4 mmol) of sodium bicarbonate. It was. To this reaction liquid, 50 ml of a DMF solution of 11.2 g (45.5 mmol) of 1,1,2,2,2-pentafluoroethyl iodide (DMF was cooled to -30 ° C. and 1,1,2,2,2- Pentafluoroethyl iodide was dissolved), and the mixture was charged into an autoclave and stirred at 110 ° C. for 9 hours. After standing overnight at room temperature, water and ethyl acetate were added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, saturated aqueous sodium hydrogen carbonate solution and saturated brine. After drying the organic layer over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (developing solvent; hexane: ethyl acetate = 10: 1 → 5: 1). 1.95 g (21% yield) of the title compound was produced.
¹ H-NMR (CDCl ₃ , ppm) δ 4.53 (2H, broadcast-s), 6.81 (1H, d, J = 8.3 Hz), 7.48 (1H, d, J = 8.3 Hz) , 7.63 (1H, broadcast-s).

<18-2>
Preparation of 2-bromo-4- (perfluoroethyl) -6- (trifluoromethyl) aniline

The title compound was prepared from 4- (perfluoroethyl) -2- (trifluoromethyl) aniline according to the method 1-2 in Example 1.
¹ H-NMR (CDCl ₃ , ppm) δ 5.08 (2H, broadcast-s), 7.62 (1H, s), 7.80 (1H, s).

<18-3>
Preparation of N- (2-bromo-4- (perfluoroethyl) -6- (trifluoromethyl) phenyl) -3-nitrobenzamide

To 20 ml of a pyridine solution of 2.50 g (6.99 mmol) of 2-bromo-4- (perfluoroethyl) -6- (trifluoromethyl) aniline was added 2.72 g (14.7 mmol) of 3-nitrobenzoyl chloride, and 100 Stir at 12 ° C. for 12 hours. Water and ethyl acetate were added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with 1M hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated brine. The organic layer was dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. THF and an aqueous sodium hydroxide solution were added to the resulting residue, and the mixture was stirred at room temperature for 8 hours. The reaction solution is extracted and dried in the same manner as above, and the residue obtained by distilling off the solvent under reduced pressure is purified by silica gel column chromatography (developing solvent; hexane: ethyl acetate = 7: 1 → 5: 1). Produced 0.202 g (6% yield) of the title compound.
¹ H-NMR (CDCl ₃ , ppm) δ 7.75 (1H, s), 7.78 (1H, t, J = 7.8 Hz), 7.94 (1H, s), 8.17 (1H, s ), 8.29-8.30 (1H, m), 8.50-8.52 (1H, m), 8.78 (1H, t, J = 2.0 Hz).

<18-4>
Preparation of 3-amino-N- (2-bromo-4- (perfluoroethyl) -6- (trifluoromethyl) phenyl) benzamide

The title compound was prepared from N- (2-bromo-4- (perfluoroethyl) -6- (trifluoromethyl) phenyl) -3-nitrobenzamide according to the method of Example 1-5.
¹ H-NMR (CDCl ₃ , ppm) δ 3.89 (2H, broadcast-s), 6.90-6.92 (1H, m), 7.23-7.32 (3H, m), 7.64 (1H, s), 7.90 (1H, s), 8.13 (1H, s).

<18-5>
Preparation of 3-benzamide-N- (2-bromo-4- (perfluoroethyl) -6- (trifluoromethyl) phenyl) benzamide (Compound No. 6-5913)

The title compound was prepared from 3-amino-N- (2-bromo-4- (perfluoroethyl) -6- (trifluoromethyl) phenyl) benzamide according to the method of Example 1-7.
¹ H-NMR (CDCl ₃ , ppm) δ 7.51-7.62 (4H, m), 7.72 (1H, dd, J = 1.5, 7.8 Hz), 7.89-8.00 ( 6H, m), 8.14 (1H, s), 8.27 (1H, t, J = 2.0 Hz).

<Example 19>
Preparation of 3-benzamido-N- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -4-cyanobenzamide (Compound No. 1-627)

<19-1>
Preparation of N- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -4-fluoro-3-nitrobenzamide

According to the method of Example 4-4-3, 4-fluoro-3-nitrobenzoyl chloride prepared from 4-fluoro-3-nitrobenzoic acid and thionyl chloride and 2- The title compound was prepared from bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) aniline.
¹ H-NMR (CDCl ₃ , ppm) δ 7.47-7.50 (1H, m), 7.92 (2H, d, J = 5.9 Hz), 8.16 (1H, s), 8.23 -8.28 (1H, m), 8.65-8.67 (1H, m).

<19-2>
Preparation of N- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -4-cyano-3-nitrobenzamide

To 5 ml of a DMF solution of 0.500 g (0.870 mmol) of N- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -4-fluoro-3-nitrobenzamide 0.0639 g (1.31 mmol) of sodium cyanide was added and stirred at room temperature for 10 hours. Water and ethyl acetate were added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with 10% aqueous sodium hydroxide solution and saturated brine. The organic layer was dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography to produce 0.0500 g (yield 10%) of the title compound.
¹ H-NMR (CDCl ₃ , ppm) δ 7.80 (1H, s), 7.96 (1H, s), 8.12-8.14 (1H, m), 8.18 (1H, s), 8.36 (1H, dd, J = 2.0, 8.3 Hz), 8.84 (1H, d, J = 1.5 Hz).

<19-3>
Preparation of 3-amino-N- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -4-cyanobenzamide

According to the method of Example 1-5, from N- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -4-cyano-3-nitrobenzamide The compound was prepared.
¹ H-NMR (CDCl ₃ , ppm) δ 4.68 (2H, broadcast-s), 7.18 (1H, dd, J = 1.9, 8.3 Hz), 7.29 (1H, s), 7 .52-7.55 (1H, m), 7.68 (1H, s), 7.92 (1H, s), 8.14 (1H, d, J = 1.5 Hz).

<19-4>
Preparation of 3-benzamido-N- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -4-cyanobenzamide (Compound No. 1-627)

According to the method of Example 1-7, from 3-amino-N- (2-bromo-4- (perfluoropropan-2-yl) -6- (trifluoromethyl) phenyl) -4-cyanobenzamide The compound was prepared.
¹ H-NMR (CDCl ₃ , ppm) δ 7.56-7.59 (3H, m), 7.64-7.66 (1H, m), 7.80-7.87 (2H, m), 7 .94-7.97 (2H, m), 8.16 (1H, s), 8.46 (1H, s), 8.57 (1H, s), 9.16 (1H, s).

  Next, although the typical formulation example concerning this invention is shown, this invention is not limited to these. In the preparation examples, “parts” means “parts by weight”.

Formulation Example 1 (Dust)
As a powder containing 5% active ingredient, 5 parts of an amide derivative of Compound No. 7-1574, 94.5 parts of clay and 0.5 part of Doreles B (Mitsui Chemicals Agro) are mixed and ground uniformly. An insect control composition was obtained.

Formulation Example 2 (wettable powder)
Compound seeds 7-1574, 50 parts of amide derivative, 1 part of sodium lignin sulfonate, 5 parts of white carbon and 44 parts of diatomaceous earth are mixed and pulverized as a wettable powder containing an active ingredient of 50% to control insect damage for plant seeds. I got a thing.

Formulation Example 3 (Flowable)
20 parts of an amide derivative of Compound No. 7-1574, 5 parts of propylene glycol, 5 parts of polyoxyethylene oleate, 5 parts of polyoxyethylene diallyl ether sulfate, 0.2 part of a silicon-based antifoaming agent, and 64.8 water Part was wet pulverized with a sand grinder to obtain a plant seed insect control composition as a flowable agent with an active ingredient of 20%.

Formulation Example 4 (Emulsion)
As an emulsion containing 10% active ingredient, 10 parts of amide derivative of Compound No. 7-1574, 10 parts of cyclohexane, 60 parts of xylene and 20 parts of Solpol (surfactant manufactured by Toho Chemical) are uniformly mixed. An insect pest control composition was obtained.

Formulation Example 5 (Granule wettable powder)
Compound No. 7-1574 20 parts of amide derivative, 3 parts of CMC sodium, 5 parts of alkyl sulfate ester, 72 parts of clay are uniformly mixed, and then kneaded, granulated, dried and sized, and contains 20% active ingredient As a granule wettable powder, a plant seed insect control composition was obtained.

  Compound Nos. 7-1733, 6-460, 6-1260, and 7-1104 were also prepared in the same manner as in Formulation Examples 1 to 5, respectively, Insect damage control compositions for plant seeds were obtained.

  Next, the usefulness of the composition of the present invention as a plant seed pest control composition (seed treatment agent) will be specifically described in the following test examples, but the present invention is not limited thereto. . In the following test examples, a wettable powder was prepared in the same manner as in Preparation Example 2.

<Test Example 1>
Corn corn borer (Ostrinia furnacalis) control test The corn seeds were powdered to a prescribed dose. Three seeds treated with the drug were sown in a plastic pot having a diameter of 9 cm, and five 14-year-old larvae were released from the seed 14 days after sowing (three-line system). Six days after the release, the number of dead strains was investigated, and the dead strain rate was calculated. In addition, the presence or absence of phytotoxicity was determined by visual observation. The results are shown in Table 53.

<Test Example 2>
Corn cabbage moth (Agrotis segetum) control test The corn seeds were powdered to a prescribed dose. Five seeds treated with chemicals were sown in 1 / 1000a planter, and five third-instar larvae were released 9 days after sowing (two-line system). After 5 days of insect release, life and death were investigated, and the death rate was calculated. In addition, the presence or absence of phytotoxicity was determined by visual observation. The results are shown in Table 54.

<Test Example 3>
Onion onion fly (Delia antiqua) control test The onion seeds were powdered to a predetermined dose. Ten seeds treated with the drug were sown in a 1 / 10000a pot, and about 100 eggs of onion fly were inoculated 12 days after sowing (two-line system). 12 days after the inoculation, the number of strains damaged by the onion fly hatching larvae was investigated, and the rate of damaged strains was calculated. In addition, the presence or absence of phytotoxicity was determined by visual observation. The results are shown in Table 55.

<Test Example 4>
Komatsuna's Phyllotreta striolata pest control test Komatsuna seeds were powdered to give a prescribed dose. The seeds treated with the drug were sown at 15 cm intervals and 3 rows in the field, and 2 weeks after sowing, the number of damaging insects on the leaf of Komatsuna was investigated (one continuous system). In addition, the presence or absence of phytotoxicity was determined by visual observation. The results are shown in Table 56.

  The amide derivatives of Compound Nos. 6-1574, 6-1733, 7-424, 7-1577, 7-1730, and 7-1732 were also tested in the same manner as in Test Examples 1 to 4, and the amide derivatives used above In the same way, it showed excellent insect control effects.

Claims (21)

The following general formula (1)

{In general formula (1),
A represents a carbon atom, an oxygen atom, a nitrogen atom, an oxidized nitrogen atom, or a sulfur atom.
K together with the two carbon atoms to which A and A are attached, benzene, pyridine, pyridine-N-oxide, pyrimidine, pyrazine, pyridazine, triazine, pyrrole, pyrazole, imidazole, oxazole, isoxazole, thiazole, isothiazole, A group of nonmetallic atoms necessary for forming a cyclic linking group derived from furan, thiophene, oxadiazole, thiodiazole or triazole is shown.

X is a hydrogen atom, halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C9 cycloalkyl group, C3-C9 halocycloalkyl group, C2-C6 alkenyl group, C2-C6 haloalkenyl group, C2 -C6 alkynyl group, C2-C6 haloalkynyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C2-C6 alkenyloxy group, C2-C6 haloalkenyloxy group, C2-C6 alkynyloxy group, C2-C6 Haloalkynyloxy group, C3-C9 cycloalkoxy group, C3-C9 halocycloalkoxy group, C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 Alkylsulfonyl group, C1-C6 haloalkyl Sulfonyl group, C1-C6 alkylsulfonyloxy group, C1-C6 haloalkylsulfonyloxy group, C2-C7 alkylcarbonyl group, C2-C7 haloalkylcarbonyl group, C3-C7 alkenylcarbonyl group, C3-C7 haloalkenylcarbonyl group, C3- C7 alkynylcarbonyl group, C3-C7 haloalkynylcarbonyl group, C4-C10 cycloalkylcarbonyl group, C4-C10 halocycloalkylcarbonyl group, C2-C7 alkylcarbonyloxy group, C2-C7 haloalkylcarbonyloxy group, arylcarbonyloxy group C2-C7 alkoxycarbonyl group, C2-C7 haloalkoxycarbonyl group, C3-C7 alkenyloxycarbonyl group, C3-C7 haloalkenyloxycarbonyl group, C3-C7 Alkynyloxycarbonyl group, C3-C7 haloalkynyloxycarbonyl group, C4-C10 cycloalkyloxycarbonyl group, C4-C10 halocycloalkyloxycarbonyl group, C2-C7 alkylcarbonylamino group, C2-C7 haloalkylcarbonylamino group, C2-C7 alkoxycarbonylamino group, C2-C7 haloalkoxycarbonylamino group, C2-C7 alkoxycarbonyloxy group, C2-C7 haloalkoxycarbonyloxy group, arylcarbonylamino group, amino group, carbamoyl group, cyano group, hydroxy group , Pentafluorosulfanyl group, C1-C6 alkylamino group, C1-C6 haloalkylamino group, C2-C6 alkenylamino group, C2-C6 haloalkenylamino group, C2-C6 alkini Ruamino group, C2-C6 haloalkynylamino group, C3-C9 cycloalkylamino group, C3-C9 halocycloalkylamino group, C2-C7 alkylaminocarbonyl group, C2-C7 haloalkylaminocarbonyl group, C3-C7 alkenylaminocarbonyl Group, C3-C7 haloalkenylaminocarbonyl group, C3-C7 alkynylaminocarbonyl group, C3-C7 haloalkynylaminocarbonyl group, C4-C10 cycloalkylaminocarbonyl group, C4-C10 halocycloalkylaminocarbonyl group, phenyl group, Or when a heterocyclic group is shown and there are two or more X, each X may mutually be same or different.
n shows the integer of 0-4.
T represents a -C ₍₌ G ₁₎ -Q 1 or _{-C (= G 1) -G 2} Q 2,.
G ₁ and G ₂ each independently represent an oxygen atom or a sulfur atom,
Q ₁ and Q ₂ are
Hydrogen atom,
A C1-C6 alkyl group,
A C1-C6 haloalkyl group,
A C2-C6 alkenyl group,
A C2-C6 haloalkenyl group,
A C2-C6 alkynyl group,
A C2-C6 haloalkynyl group,
A C3-C9 cycloalkyl group,
A C3-C9 halocycloalkyl group,
Benzyl group,
An optionally substituted phenyl group,
A naphthyl group,
Or an optionally substituted heterocyclic group,
Indicates.

Y ₁ and Y ₅ each independently represent a halogen atom, a C1-C6 haloalkoxy group, or a C1-C3 haloalkyl group,
Y ₂ and Y ₄ each independently represent a hydrogen atom, a halogen atom, or a C1-C4 alkyl group,
Y ₃ represents a C2-C5 haloalkyl group.

In Q ₁ and Q ₂ , the optionally substituted phenyl group and optionally substituted heterocyclic group substituents are:
Halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C9 cycloalkyl group, C3-C9 halocycloalkyl group, C2-C6 alkenyl group, C2-C6 haloalkenyl group, C2-C6 alkynyl group, C2 -C6 haloalkynyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C2-C6 alkenyloxy group, C2-C6 haloalkenyloxy group, C2-C6 alkynyloxy group, C2-C6 haloalkynyloxy group, C3 -C9 cycloalkoxy group, C3-C9 halocycloalkoxy group, C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1- A C6 haloalkylsulfonyl group, 2-C7 alkylcarbonyl group, C2-C7 haloalkylcarbonyl group, C3-C7 alkenylcarbonyl group, C3-C7 haloalkenylcarbonyl group, C3-C7 alkynylcarbonyl group, C3-C7 haloalkynylcarbonyl group, C4-C10 cycloalkylcarbonyl Group, C4-C10 halocycloalkylcarbonyl group, C2-C7 alkylcarbonyloxy group, C2-C7 haloalkylcarbonyloxy group, C1-C6 alkylsulfonyloxy group, C1-C6 haloalkylsulfonyloxy group, C2-C7 alkoxycarbonyl group, C2-C7 haloalkoxycarbonyl group, C3-C7 alkenyloxycarbonyl group, C3-C7 haloalkenyloxycarbonyl group, C3-C7 alkynyloxycarbonyl group, C3-C7 halo Lucinyloxycarbonyl group, C4-C10 cycloalkyloxycarbonyl group, C4-C10 halocycloalkyloxycarbonyl group, C2-C7 alkylcarbonylamino group, C2-C7 haloalkylcarbonylamino group, C2-C7 alkoxycarbonylamino group, C2 -C7 haloalkoxycarbonylamino group, C1-C6 alkylamino group, C1-C6 haloalkylamino group, C2-C6 alkenylamino group, C2-C6 haloalkenylamino group, C2-C6 alkynylamino group, C2-C6 haloalkynylamino group Group, C3-C9 cycloalkylamino group, C3-C9 halocycloalkylamino group, C2-C7 alkylaminocarbonyl group, C2-C7 haloalkylaminocarbonyl group, C3-C7 alkenylaminocarbonyl group C3-C7 haloalkenylaminocarbonyl group, C3-C7 alkynylaminocarbonyl group, C3-C7 haloalkynylaminocarbonyl group, C4-C10 cycloalkylaminocarbonyl group, C4-C10 halocycloalkylaminocarbonyl group, amino group, carbamoyl One or more substituents selected from a group, a cyano group, a nitro group, a hydroxy group, a pentafluorosulfanyl group, an optionally substituted phenyl group, and an optionally substituted heterocyclic group In the case where there are two or more substituents, each substituent may be the same or different.

Further, the heterocyclic group in X, Q ₁ and Q ₂ is a pyridyl group, a pyridine-N-oxide group, a pyrimidinyl group, a pyrazinyl group, a pyridazyl group, a furyl group, a thienyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, A thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a pyrrolyl group, an imidazolyl group, a triazolyl group, a pyrazolyl group, or a tetrazolyl group;

G ₃ represents an oxygen atom or a sulfur atom.

R ₁ and R ₂ each independently have a hydrogen atom, oxygen atom, halogen atom, hydroxy group, nitro group, nitroso group, trimethylsilyl group, t-butyldimethylsilyl group, cyano group, amino group, or substituent. An optionally substituted C1-C6 alkyl group, an optionally substituted C1-C6 haloalkyl group, a C2-C7 alkylcarbonyl group, a C2-C7 haloalkylcarbonyl group, an optionally substituted C2-C6 An alkenyl group, an optionally substituted C2-C6 haloalkenyl group, an optionally substituted C2-C6 alkynyl group, an optionally substituted C2-C6 haloalkynyl group, C2-C7 alkoxycarbonyl group, C2-C7 haloalkoxycarbonyl group, C3-C7 alkenyloxycarbonyl group, C3-C7 haloal group Nyloxycarbonyl group, C3-C7 alkynyloxycarbonyl group, C3-C7 haloalkynyloxycarbonyl group, phenoxycarbonyl group, C2-C7 alkylaminocarbonyl group, C2-C7 haloalkylaminocarbonyl group, C2-C7 alkylcarbonyloxy group, C2-C7 haloalkylcarbonyloxy group, benzoyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group , C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, a benzenesulfonyl group, benzylsulfonyl group, a benzyl group or,, -C (= O) C (= O) R 7 ( wherein, _{R 7} is C1- A C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group or a C1-C6 haloalkoxy group).
} The plant seed insect control composition which contains at least 1 sort (s) of the amide derivative represented by this as an active ingredient.

However, the case where the amide derivative represented by the general formula (1) is any one of the following (A) to (I) is excluded.
(A) In the general formula (1), K is a group of nonmetallic atoms necessary for forming a cyclic linking group derived from pyridine together with two carbon atoms to which A and A are bonded, ₁ is a halogen atom, _{Y 5} is C1-C6 haloalkoxy group, when T is _{-C (= G 1) -Q 1} .
(B) In the above general formula (1), K is pyrrole, pyrazole, imidazole, oxazole, isoxazole, thiazole, isothiazole, furan, thiophene, oxadiazole together with the two carbon atoms to which A and A are bonded. , A non-metallic atom group necessary for forming a cyclic linking group derived from thiodiazole or triazole, wherein Y ₁ and Y ₅ are each independently a halogen atom, and T is —C (═G ₁ ) — When G ₂ Q ₂ .
(C) In the above general formula (1), K is pyrrole, pyrazole, imidazole, oxazole, isoxazole, thiazole, isothiazole, furan, thiophene, oxadiazole together with the two carbon atoms to which A and A are bonded. , A non-metallic atom group necessary for forming a cyclic linking group derived from thiodiazole or triazole, wherein T is —C (═G ₁ ) —Q ₁ , Y ₁ is a halogen atom, and Y ₅ Is a halogen atom or a haloalkoxy group.
(D) The following general formula (2)

{In General Formula (2), Y _{2 to} Y ₄ , Q ₁ , G ₁ , G ₃ , R ₁ , and R ₂ are Y _{2 to} Y ₄ , Q ₁ , G ₁ , G in General Formula (1). ₃ , R ₁ , and R ₂ are respectively synonymous, Y ₁ is a halogen atom, and Y ₅ is a C1-C2 haloalkoxy group. } Is an amide derivative represented by:
(E) In the general formula (2), Y ₁ and Y ₅ are halogen atoms, and Y ₃ is a C2-C3 haloalkyl group.
(F) The following general formula (3)

{In General Formula (3), Y ₁ and Y ₅ are each independently a halogen atom, X ₁ and X ₃ are each independently a hydrogen atom or a fluorine atom, and Q ₁ is a general formula (1) a synonymous with _{Q 1} in, _{R 1} is a hydrogen atom or a methyl group, _{Y 3} is a C3-C4 perfluoroalkyl group. } Is an amide derivative represented by:
(G) The following general formula (4)

{In General Formula (4), X ₁ is a fluorine atom, X ₂ , X ₃ , and X ₄ are hydrogen atoms, Y ₁ and Y ₅ are different from each other, and are a bromine atom or a trifluoromethoxy group, Y ₂ and Y ₄ are hydrogen atoms, Y ₃ is a heptafluoroisopropyl group, Q ₁ is a phenyl group or a 2-chloropyridin-3-yl group, and R ₁ and R ₂ are different from each other, A hydrogen atom or a methyl group.
Alternatively, X ₁ is a fluorine atom, X ₂ , X ₃ , and X ₄ are hydrogen atoms, Y ₁ and Y ₅ are bromine atoms, Y ₂ and Y ₄ are hydrogen atoms, and Y ₃ is pentafluoro An ethyl group, Q ₁ is a 2-fluorophenyl group, and R ₁ and R ₂ are each independently a hydrogen atom or a methyl group;
} Is an amide derivative represented by:
(H) The following general formula (5)

{In General Formula (5), Y ₁ and Y ₅ are each independently a halogen atom, X ₁ is a hydrogen atom or a fluorine atom, Q ₂ is a 2,2,2-trichloroethyl group, 3 , 3,3-trifluoro-n-propyl group and Y ₃ is a C2-C4 haloalkyl group. } Is an amide derivative represented by:
(I) The following general formula (6)

{In General Formula (6), Y ₁ and Y ₅ are each independently a halogen atom, Q ₂ is synonymous with Q ₂ in General Formula (1), and R ₁ is a hydrogen atom or a methyl group. Y ₃ is a C3-C4 haloalkyl group. } Is an amide derivative represented by:
The amide derivative represented by the general formula (1) is represented by the following general formula (7).

{In General Formula (7), n is 4, and X, Y _{1 to} Y ₅ , Q ₁ , G ₁ , G ₃ , R ₁ , and R ₂ represent X, Y ₁ to R in General Formula (1), respectively. Y ₅ , Q ₁ , G ₁ , G ₃ , R ₁ , and R ₂ are synonymous with each other. } The insect control composition for plant seeds of Claim 1 represented by these.
The amide derivative represented by the general formula (7) is represented by the following general formula (8).

{In General Formula (8), Q ₁ represents a phenyl group which may have a substituent or a pyridyl group which may have a substituent.
X ₁ , X ₂ , X ₃ , and X ₄ each independently represent a hydrogen atom or a fluorine atom.
R ₁ and R ₂ each independently represent a hydrogen atom or a C1-C3 alkyl group.
Y ₁ and Y ₅ each independently represent a halogen atom, a C1-C3 haloalkoxy group or a C1-C3 haloalkyl group, and Y ₂ and Y ₄ each independently represent a hydrogen atom, a halogen atom or a C1-C4 alkyl group. shows, _{Y 3} represents a C3-C4 haloalkyl group.
However, when Y ₁ and Y ₅ are simultaneously halogen atoms, at least one of X ₁ and X ₂ is a fluorine atom. When Y ₁ or Y ₅ is a C1-C3 haloalkoxy group, X ₂ is a fluorine atom.
} The insect pest control composition for plant seeds of Claim 2 represented by these. In the general formula (8), Y ₃ is a plant seed for insect damage control composition according to claim 3, wherein the C3-C4 perfluoroalkyl group. In the general formula (8), Y ₁ and Y ₅ are each independently a chlorine atom, bromine atom, iodine atom, trifluoromethoxy group, trifluoromethyl group, or pentafluoroethyl group, and Y ₂ and Y ₄ The insect control composition for plant seeds according to claim 4, wherein is a hydrogen atom. In the general formula (8), X ₁ and X ₂ are each independently a hydrogen atom or a fluorine atom, X ₃ and X ₄ are seeds for insect damage control composition according to claim 5 is a hydrogen atom. In the general formula (8), each of R ₁ and R ₂ independently, plant seeds for insect damage control composition according to claim 6 is a hydrogen atom or a methyl group. In the general formula (8), Q ₁ represents a halogen atom, C1 haloalkyl group, according to claim 7, which is optionally substituted phenyl or pyridyl group selected from a nitro group and a cyano group Plants An insect control composition for seeds. In the general formula (8), seeds for insect damage control composition according to claim 8 number of the substituents in Q ₁ is a 1 or 2. In the general formula (7), Y ₃ is a C2-C4 perfluoroalkyl group, Y ₂ and Y ₄ are hydrogen atoms, Y ₁ and Y ₅ are halogen atoms or C1-C3 haloalkyl groups. Te, one of Y ₁ and Y _5, plant seeds for insect damage control composition according to claim 2, wherein the C1-C3 haloalkyl group.   In the said General formula (7), four X is respectively independently a hydrogen atom, a halogen atom, or a cyano group, The insect-control insecticide composition for plant seeds of Claim 10. The amide derivative represented by the general formula (1) is represented by the following general formula (9).

{In General Formula (9), n is 4, X, Y _{1 to} Y ₅ , Q ₂ , G _{1 to} G ₃ , R ₁ , and R ₂ are X, Y ₁ to R in General Formula (1) Y ₅ , Q ₂ , G _{1 to} G ₃ , R ₁ , and R ₂ have the same meanings. } The insect control composition for plant seeds of Claim 1 represented by these. In the general formula (9), Y ₃ is a C2-C4 perfluoroalkyl group, Y ₂ and Y ₄ are hydrogen atoms, Y ₁ and Y ₅ are halogen atoms or C1-C3 haloalkyl groups, , Y ₁ , Y ₅ is a C1-C3 haloalkyl group. The insect control composition for plant seeds according to claim 12.   In the said General formula (9), four X is respectively independently a hydrogen atom, a halogen atom, or a cyano group, The insect-control insecticide composition for plant seeds of Claim 13.   In the general formula (1), K represents pyridine, pyridine-N-oxide, pyrimidine, pyrazine, pyridazine, triazine, pyrrole, pyrazole, imidazole, oxazole, isoxazole together with two carbon atoms to which A and A are bonded. The insect control composition for plant seeds according to claim 1, which is a group of non-metallic atoms necessary to form a cyclic linking group derived from thiothiazole, isothiazole, furan, thiophene, oxadiazole, thiodiazole or triazole. In the general formula (1), Y ₃ is a C2-C4 perfluoroalkyl group, Y ₂ and Y ₄ are hydrogen atoms, Y ₁ and Y ₅ are halogen atoms or C1-C3 haloalkyl groups, , Y ₁ or Y ₅ is a C1-C3 haloalkyl group, The insect control composition for plant seeds according to claim 15.   In the general formula (1), K forms a cyclic linking group derived from pyridine, pyridine-N-oxide, pyrrole, thiazole, furan, or thiophene together with two carbon atoms to which A and A are bonded. The insect control composition for plant seeds according to claim 16, which is a nonmetallic atom group necessary for the plant.   A method for preventing insect damage, comprising applying the insect control composition for plant seeds according to any one of claims 1 to 17 to plant seeds.   The method for preventing insect damage according to claim 18, wherein the method applied to the plant seed is a spraying treatment, a smearing treatment, a dipping treatment or a dressing treatment on the seed.   The plant seeds are corn, soybean, cotton, rice, sugar beet, wheat, barley, sunflower, tomato, cucumber, eggplant, spinach, sweet pea, pumpkin, sugar cane, tobacco, pepper, and oilseed rape seed, taro, potato, 20. The method for preventing insect damage according to claim 18 or 19, wherein the method is selected from sweet potato and konjac seeds, edible lily and tulip bulbs.   A plant seed to which the insect pest control composition for plant seed according to any one of claims 1 to 17 is applied.