CN106572657B - Pest control composition and application thereof - Google Patents

Abstract

Include the compound (wherein symbol is defined as in the description) and 2 by indicating in formula (1), 4- dioxo -1- (5- Pyrimidylmethyl) -3- [3- (trifluoromethyl) phenyl] -2H- pyrido [1,2-a] pyrimidineThe pest control composition of inner salt has special preventing efficiency for harmful organism.Provide the pest control composition that there is special preventing efficiency for harmful organism.

Description

Pest control compositions and uses thereof

technical field

The present invention relates to compositions for controlling pests and methods for controlling pests.

Background technique

Heretofore, many compounds have been known as active ingredients of compositions for controlling pests (see Patent Documents 1 to 3, and Non-Patent Document 1).

Citation List

Patent Literature

Patent Document 1: WO 2013/018928 pamphlet

Patent Document 2: WO 2012/092115 pamphlet

Patent Document 3: WO 2014/104407 Pamphlet

Non-patent literature

Non-Patent Document 1: THE Pesticide Manual - 16th Edition, published by BCPC, ISBN9781901396867

SUMMARY OF THE INVENTION

(Technical problem to be solved by the present invention)

An object of the present invention is to provide a composition for controlling pests having excellent controlling efficacy against pests.

(means to solve the problem)

The inventors of the present invention have intensively studied to find a composition for controlling pests having excellent controlling effect on pests. As a result, they have found that a composition comprising the compound represented by the formula (1) mentioned below has an excellent controlling effect against pests, and

2,4-Dioxo-1-(5-pyrimidinylmethyl)-3-[3-(trifluoromethyl)phenyl]-2H-pyrido[1,2-a]pyrimidine Inner salt (hereinafter, referred to as "Triflumezopyrim").

The present invention provides, for example, the following embodiments.

[1] A composition for controlling harmful organisms, the composition for controlling harmful organisms comprising

Compounds represented by formula (1):

in,

A ¹ represents -NR ⁷ -, an oxygen atom or a sulfur atom,

A ² means =N-, =N(→O)- or =CR ⁸ -,

Q means =N- or =N(→O)-,

R ¹ represents a C1-C6 alkyl optionally having one or more atoms or groups selected from group X,

R ² , R ³ and R ⁴ are the same or different from each other, and each represents a C1-C6 alkyl group optionally having one or more atoms or groups selected from the X group, -OR ¹⁰ , -S(O) _m R ¹⁰ , -S(O) ₂ NR ¹⁰ R ¹¹ , -NR ¹⁰ R ¹¹ , -NR ¹⁰ CO ₂ R ¹¹ , -NR ¹⁰ C(O)R ¹¹ , -CO ₂ R ¹⁰ , -C(O)R ¹⁰ , -C(O)NR ¹⁰ R ¹¹ , -SF ₅ , cyano group, nitro group, halogen atom or hydrogen atom,

R ⁵ and R ⁶ are the same or different from each other, and each represents a C1-C6 alkyl group optionally having one or more atoms or groups selected from group X, -OR ¹⁰ , -S(O) _m R ¹⁰ , -S(O) ₂ NR ¹⁰ R ¹¹ , -NR ¹⁰ R ¹¹ , -NR ¹⁰ CO ₂ R ¹¹ , -NR ¹⁰ C(O)R ¹¹ , -CO ₂ R ¹⁰ , -C(O)R ¹⁰ , - C(O)NR ¹⁰ R ¹¹ , -OC(O)R ¹⁰ , -SF ₅ , a cyano group, a nitro group, a halogen atom or a hydrogen atom (provided that R ⁵ and R ⁶ do not simultaneously represent a hydrogen atom),

R ⁷ represents C1-C6 alkyl optionally having one or more atoms or groups selected from group W, -CO ₂ R ¹⁰ , -C(O)R ¹⁰ , -CH ₂ CO ₂ R ¹⁰ , C3 -C6 cycloalkyl or hydrogen atom,

R ⁸ represents C1-C6 alkyl optionally having one or more halogen atoms, -OR ¹⁰ , -S(O) _m R ¹⁰ , -NR ¹⁰ R ¹¹ , -CO ₂ R ¹⁰ , -C(O) R ¹⁰ , a cyano group, a nitro group, a halogen atom or a hydrogen atom,

R ¹⁰ and R ¹¹ are the same or different from each other, and each represents a C1-C6 alkyl group or a hydrogen atom optionally having one or more atoms or groups selected from the group X (provided: at -S(O) _m In R ¹⁰ , when m is 1 or 2, R ¹⁰ does not represent a hydrogen atom),

m independently of each other represents 0, 1 or 2, and

n represents 0, 1 or 2,

Group X: consisting of C1-C6 alkoxy optionally having one or more halogen atoms, C3-C6 cycloalkyl optionally having one or more halogen atoms or one or more C1-C3 alkyl, the group of cyano, hydroxyl and halogen atoms,

Group W: C1-C6 alkoxy optionally having one or more halogen atoms, C3-C6 cycloalkyl optionally having one or more halogen atoms, hydroxy, halogen atom or cyano], and

2,4-Dioxo-1-(5-pyrimidinylmethyl)-3-[3-(trifluoromethyl)phenyl]-2H-pyrido[1,2-a]pyrimidine Inner salt (triflumezopyrim) (hereinafter, referred to as "the composition of the present invention").

[2] The composition for controlling pests described in [1], wherein A ¹ represents -NMe-, an oxygen atom or a sulfur atom, and A ² represents =N-, =N(→O)- or = CH-, R ¹ represents a C1-C6 alkyl group optionally having one or more halogen atoms, R ² and R ⁴ represent a hydrogen atom, and R ³ represents a C1-C3 alkane optionally having one or more halogen atoms radical or a hydrogen atom, R ⁵ represents a C1-C3 alkyl group optionally having one or more halogen atoms, -OR ¹⁰ or -S(O) _m R ¹⁰ , R ⁶ represents -NR ¹⁰ R ¹¹ or a hydrogen atom, And R ¹⁰ and R ¹¹ independently of each other represent a C1-C3 alkyl group optionally having one or more halogen atoms.

[3] The composition for controlling pests described in [1] or [2], wherein A ¹ represents -NMe-.

[4] The composition for controlling pests described in [1] or [2], wherein A ¹ represents an oxygen atom.

[5] The composition for controlling pests described in any one of [1] to [4], wherein the compound represented by the formula (1) is combined with 2,4-dioxo-1-( 5-pyrimidinylmethyl)-3-[3-(trifluoromethyl)phenyl]-2H-pyrido[1,2-a]pyrimidine The ratio of the inner salt is in the range of 100:1 to 1:100 by weight.

[6] The composition for controlling pests described in any one of [1] to [4], wherein the compound represented by the formula (1) is combined with 2,4-dioxo-1-( 5-pyrimidinylmethyl)-3-[3-(trifluoromethyl)phenyl]-2H-pyrido[1,2-a]pyrimidine The ratio of the inner salt is in the range of 10:1 to 1:10 by weight.

[7] A method for controlling harmful organisms, the method comprising applying an effective amount of the method for controlling harmful organisms described in any one of [1] to [6] to the harmful organisms or a habitat where the harmful organisms live biological composition.

[8] A method for controlling pests, the method comprising applying an effective amount of any of [1] to [6] to a plant, plant seed, bulb or soil for cultivating the plant The described compositions for controlling pests.

[9] A seed or bulb of a plant to which an effective amount of the composition for controlling pests described in any one of [1] to [6] is attached.

[Effect of invention]

The present invention can control harmful organisms.

Detailed ways

The composition for controlling pests of the present invention comprises the above-mentioned compound represented by formula (1) (hereinafter, referred to as "the present compound") and triflumezopyrim.

Groups as described herein are explained below.

As used herein, the expression "Ca-Cb alkyl" refers to a straight or branched chain hydrocarbon group having "a" to "b" carbon atoms.

The expression "Ca-Cb haloalkyl" denotes a straight or branched chain hydrocarbon group having "a" to "b" carbon atoms, wherein one or more hydrogen atoms attached to the carbon atoms are replaced by one or more halogen atoms. When two or more halogen atoms are present, the halogen atoms may be the same or different from each other.

The expression "Ca-Cb alkoxy" denotes a straight or branched chain alkyl-O- group having "a" to "b" carbon atoms.

The expression "Ca-Cb cycloalkyl" denotes a saturated cyclic hydrocarbon group having "a" to "b" carbon atoms.

As used herein, the expression "optionally having one or more atoms or groups selected from group X" means that when more than two atoms or groups are present, the atoms or groups selected from group X may be the same as each other or different.

As used herein, the expression "optionally having one or more atoms or groups selected from group W" means that when two or more atoms or groups selected from group W are present, the atoms or groups may be mutually same or different.

As used herein, the expression "optionally having one or more halogen atoms" means that when two or more halogen atoms are present, the halogen atoms may be the same or different from each other.

In the compounds of the present invention, as used herein, the term "halogen atom" refers to a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

In the compounds of the present invention, the expression "C1-C6 alkyl optionally having one or more atoms or groups selected from the group X" denotes a straight-chain or branched saturated hydrocarbon radical having 1 to 6 carbon atoms, wherein The hydrogen atom attached to the carbon atom can be optionally replaced by an atom or group selected from group X. When two or more atoms or groups are present, the atoms or groups selected from group X may be the same or different from each other.

Examples of "C1-C6 alkyl optionally having one or more atoms or groups selected from Group X" include optionally having one or more atoms or groups selected from Group X consisting of C1-C6 alkyl groups: methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, neopentyl, hexyl, methoxymethyl , ethoxymethyl, propoxymethyl, isopropoxymethyl, butoxymethyl, sec-butoxymethyl, tert-butoxymethyl, 2-methoxyethyl, 2- Ethoxyethyl, 2-propoxyethyl, 2-isopropoxyethyl, 2-butoxyethyl, 2-sec-butoxyethyl, 2-tert-butoxyethyl, tris Fluoromethyl, trichloromethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl and pentafluoroethyl, 2-hydroxyethyl, cyclopropylmethyl group, 1-methylcyclopropylmethyl, 2,2-difluorocyclopropylmethyl, trimethoxymethyl, triethoxymethyl, etc., which are selected according to the number of carbon atoms specified.

In the compounds of the present invention, the expression "C1-C6 alkyl optionally having one or more halogen atoms" denotes a straight-chain or branched saturated hydrocarbon group having 1 to 6 carbon atoms, wherein a hydrogen atom is attached to the carbon atom. It may be optionally replaced by a halogen atom, and when two or more halogen atoms are present, the halogen atoms may be the same or different from each other.

Examples of "C1-C6 alkyl optionally having one or more halogen atoms" include C1-C6 alkyl optionally having one or more halogen atoms selected from the group consisting of methyl, ethyl, Propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, neopentyl, hexyl, trifluoromethyl, trichloromethyl, 2-fluoroethyl, 2,2 - Difluoroethyl, 2,2,2-trifluoroethyl and pentafluoroethyl or heptafluoroisopropyl, etc., which are selected according to the number of carbon atoms specified.

In the compounds of the present invention, examples of "C1-C6 alkyl groups optionally having one or more atoms or groups selected from Group W" include C1-C6 alkyl groups optionally having one or more atoms or groups selected from the group consisting of: C2-C6 alkyl of atoms or groups of group W: methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, neopentyl, hexyl , trifluoromethyl, trichloromethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, pentafluoroethyl, methoxymethyl, ethoxy methyl, propoxymethyl, isopropoxymethyl, butoxymethyl, sec-butoxymethyl, isobutoxymethyl, tert-butoxymethyl, methoxyethyl, Ethoxyethyl, propoxyethyl, isopropoxyethyl, butoxyethyl, sec-butoxyethyl, isobutoxyethyl, tert-butoxyethyl and the like. When there are two or more atoms or groups selected from group W, the atoms or groups selected from group W may be the same or different from each other.

In the compound of the present invention, examples of "C1-C6 alkoxy optionally having one or more halogen atoms" include methoxy, trifluoromethoxy, ethoxy, 2,2,2-trifluoro Ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentoxy and hexyloxy.

In the compounds of the present invention, examples of "C3-C6 cycloalkyl optionally having one or more halogen atoms" include cyclopropyl, 2,2-difluorocyclopropyl, 2,2-dichlorocyclopropyl cyclopropyl, 2,2-dibromocyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.

In the compounds of the present invention, examples of "C3-C6 cycloalkyl optionally having one or more halogen atoms or one or more C1-C3 alkyl groups" include cyclopropyl, 1-methylcyclopropyl, 2-methylcyclopropyl, 1-fluorocyclopropyl, 2,2-difluorocyclopropyl, 2,2-dichlorocyclopropyl, 2,2-dibromocyclopropyl, cyclobutyl, cyclopropyl pentyl and cyclohexyl.

In the compounds of the present invention, the expression "C1-C3 haloalkyl" denotes a straight-chain or branched hydrocarbon group having 1 to 3 carbon atoms, wherein one or more hydrogen atoms attached to the carbon atoms are replaced by one or more halogen atoms , and when there are two or more halogen atoms, the halogen atoms may be the same or different from each other.

Examples of "C1-C3 haloalkyl" include fluoromethyl, chloromethyl, bromomethyl, iodomethyl, difluoromethyl, dichloromethyl, trifluoromethyl, chlorodifluoromethyl, bromodifluoro Methyl, trichloromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, pentafluoroethyl , Heptafluoropropyl, Heptafluoroisopropyl, etc.

In the compounds of the present invention, examples of "C1-C3 alkyl" include methyl, ethyl, propyl and isopropyl.

In the compounds of the present invention, examples of "C1-C3 perfluoroalkyl" include trifluoromethyl, pentafluoroethyl, heptafluoropropyl and heptafluoroisopropyl.

In a certain embodiment, examples of the compound of the present invention include compounds represented by formula (1) as listed in the following [Table 1] to [Table 20].

[Table 1]

Numbering R¹ R² R³ R⁴ R⁵ R⁶ A¹ A² n Q 1 Et H H H CF₃ H NMe N 0 N 2 Et H H H CF₃ H NMe N 1 N 3 Et H H H CF₃ H NMe N 2 N 4 Et H CF₃ H CF₃ H NMe N 0 N 5 Et H CF₃ H CF₃ H NMe N 2 N 6 Et H H H CF₂CF₃ H NMe N 0 N 7 Et H H H CF₂CF₃ H NMe N 1 N 8 Et H H H CF₂CF₃ H NMe N 2 N 9 Et H H H I H NMe N 0 N 10 Et H CF₃ H CF₃ H S N 0 N 11 Et H CF₃ H CF₃ H S N 2 N 12 Et H H H CF₃ H S N 2 N 13 Et H H H SCF₃ H NMe N 0 N 14 Et H H H SCF₃ H NMe N 1 N 15 Et H H H SCF₃ H NMe N 2 N 16 Et H H H S(O)₂CF₃ H NMe N 2 N 17 Et H CF₃ H CF₂CF₃ H NMe N 0 N 18 Et H CF₃ H CF₂CF₃ H NMe N 1 N 19 Et H CF₃ H CF₂CF₃ H NMe N 2 N 20 Et H H H S(O)CF₃ H NMe N 2 N twenty one Et H H H I H NMe CH 0 N twenty two* Et H H H CF₃ H S N(→O) 2 N twenty three Et H H H SF₅ H NMe CH 0 N twenty four Et H H H SF₅ H NMe CH 2 N 25 Et H CF₃ H S(O)₂CF₃ H NMe N 2 N

[Table 2]

[table 3]

[Table 4]

Numbering R¹ R² R³ R⁴ R⁵ R⁶ A¹ A² n Q 76 Et H H H CF₃ H NH N 0 N 77 Et H H H CF₃ H NH N 2 N 78 Et H CF₃ H CF₃ H NH N 0 N 79 Et H CF₃ H CF₃ H NH N 2 N 80 Et H H H CF₃ H O N 0 N 81 Et H H H CF₃ H O N 2 N 82 Et H CF₃ H CF₃ H O N 0 N 83 Et H CF₃ H CF₃ H O N 2 N 84 Et H H H CF₃ H O CH 0 N 85 Et H H H CF₃ H O CH 2 N 86 Et H CF₃ H CF₃ H O CH 0 N 87 Et H CF₃ H CF₃ H O CH 2 N 88 Et H H H CF₃ Cl NMe N 2 N 89 Et H CF₃ H CF₃ Cl NMe N 2 N 90 Et H H H CF₃ OC(O)Me NMe N 2 N 91 Et H CF₃ H CF₃ OC(O)Me NMe N 2 N 92 Et H H H CF₃ OH NMe N 2 N 93 Et H CF₃ H CF₃ OH NMe N 2 N 94 Et H H H CF₃ OMe NMe N 2 N 95 Et H CF₃ H CF₃ OMe NMe N 2 N 96 Et H H H CF₃ SMe NMe N 2 N 97 Et H CF₃ H CF₃ SMe NMe N 2 N 98 Et H H H CF₃ NMe₂ NMe N 2 N 99 Et H CF₃ H CF₃ NMe₂ NMe N 2 N 100 CH₂CycPr H H H CF₃ H NMe N 2 N

[table 5]

[Table 6]

[Table 7]

Numbering R¹ R² R³ R⁴ R⁵ R⁶ A¹ A² n Q 151 tBu H H H CF₃ H NMe N 0 N 152 tBu H H H CF₃ H NMe N 1 N 153 tBu H H H CF₃ H NMe N 2 N 154 CF₃ H H H CF₃ H NMe N 0 N 155 CF₃ H H H CF₃ H NMe N 1 N 156 Et H H H CF₃ H NEt N 0 N 157 Et H H H CF₃ H NEt N 1 N 158 Et H H H CF₃ H NEt N 2 N 159 Et H H H CF₃ H NPr N 0 N 160 Et H H H CF₃ H NPr N 1 N 161 Et H H H CF₃ H NPr N 2 N 162 Et H H H CF₃ H NiPr N 0 N 163 Et H H H CF₃ H NiPr N 1 N 164 Et H H H CF₃ H NiPr N 2 N 165 Et H H H CF₃ H NCycPr N 0 N 166 Et H H H CF₃ H NCycPr N 1 N 167 Et H H H CF₃ H NCycPr N 2 N 168 Et H H H CF₃ H NCH₂OEt N 0 N 169 Et H H H CF₃ H NCH₂OEt N 1 N 170 Et H H H CF₃ H NCH₂OEt N 2 N 171 Et H H H CF₃ H NCH₂OMe N 0 N 172 Et H H H Me H NMe N 0 N 173 Et H H H Me H NMe N 1 N 174 Et H H H Me H NMe N 2 N 175 Et H H H Br H NMe N 0 N

[Table 8]

[Table 9]

[Table 10]

Numbering R¹ R² R³ R⁴ R⁵ R⁶ A¹ A² n Q 226 Et Cl H H CF₂CF₃ H NMe N 1 N 227 Et Cl H H CF₂CF₃ H NMe N 2 N 228 Et H Cl H CF₃ H NMe N 0 N 229 Et H Cl H CF₃ H NMe N 1 N 230 Et H Cl H CF₂CF₃ H NMe N 1 N 231 Et H H Cl CF₃ H NMe N 0 N 232 Et H H Cl CF₃ H NMe N 1 N 233 Et H H OMe CF₃ H NMe N 0 N 234 Et H H OMe CF₃ H NMe N 1 N 235 Et H H OMe CF₃ H NMe N 2 N 236 Et H H H SH H NMe N 0 N 237 Et H H H Et H NMe N 0 N 238 Et H H H iPr H NMe N 0 N 239 Et H H H NHEt H NMe N 0 N 240 Et H H H NEt₂ H NMe N 0 N 241 Et H H H tBu H NMe N 0 N 242 Et H H H H CF₃ NMe N 0 N 243 Et F H H CF₃ H NMe N 0 N 244 Et F H H CF₃ H NMe N 1 N 245 Et F H H CF₃ H NMe N 2 N 246 Et H H H H CF₃ NMe N 1 N 247 Et H H H H CF₃ NMe N 2 N 248 Et H H H NMe₂ H NMe N 0 N 249 Et H H H NHCOMe H NMe N 0 N 250 Et H H H CH₂CF₃ H NMe N 0 N

[Table 11]

[Table 12]

[Table 13]

Numbering R¹ R² R³ R⁴ R⁵ R⁶ A¹ A² n Q 301 Et H NO₂ H CF₃ H NMe N 1 N 302 Et H NO₂ H CF₃ H NMe N 2 N 303 Et H I H SCF₃ H NMe N 2 N 304 Et H I H SO₂CF₃ H NMe N 2 N 305 Et H Br H CF₂CF₃ H NMe N 2 N 306 Et H Cl H CF₃ H S N 0 N 307 Et H Cl H CF₃ H S N 2 N 308 Et H H H C(OH)(CF₃)₂ H NMe N 0 N 309 Et H H H C(Cl)(CF₃)₂ H NMe N 0 N 310 Et H H H C(Cl)(CF₃)₂ H NMe N 1 N 311 Et H H H C(Cl)(CF₃)₂ H NMe N 2 N 312 Et H Cl H CF₂CF₃ H NMe N 2 N 313 Et H H H H CF(CF₃)₂ NMe CH 0 N 314 Et H H H CF(CF₃)₂ H NMe CH 0 N 315 Et H CF₃ H I H NMe N 2 N 316 Et H H H CF₂CF₃ H NMe CH 1 N 317 Et H H H SF₅ H NMe CH 1 N 318 Et H CF₃ H SF₅ H NMe CH 0 N 319 Et H CF₃ H SF₅ H NMe CH 1 N 320 Et H Me H CF₂CF₃ H NMe N 0 N 321 Et H Me H CF₂CF₃ H NMe N 1 N 322 Et H Me H CF₂CF₃ H NMe N 2 N 323 Et H H H I H S N 0 N 324 Et H CF₃ H I H S N 0 N 325 Et H H H CF₂CF₃ H S N 0 N

[Table 14]

[Table 15]

Numbering R¹ R² R³ R⁴ R⁵ R⁶ A¹ A² n Q 351 Et H CF₃ H CF₃ H N(CH₂)₃CH₃ N 2 N 352 Et H CF₃ H CF₃ H NCH₂CO₂Me N 2 N 353 Et H CF₃ H CF₃ H NCO₂tBu N 2 N 354 Et H CF₃ H CF₃ H NCO₂Me N 2 N 355 Et H CF₃ H CF₃ H NCOMe N 2 N 356 Et H OCF₃ H CF₃ H NMe N 0 N 357 Et H OCF₃ H CF₃ H NMe N 1 N 358 Et H CF₂CF₂CF₂CF₃ H CF₃ H NMe N 2 N 359 Et H NH₂ H CF₃ H NMe N 2 N 360 Et H NHCOCF₃ H CF₃ H NMe N 2 N 361 Et H iPr H CF₃ H NMe N 2 N 362 Et H CHO H CF₃ H NMe N 2 N 363 Bu H H H CF₃ H NMe N 0 N 364 CH₂EN H H H CF₃ H NMe N 0 N 365 CH₂tBu H H H CF₃ H NMe N 0 N 366 CH₂CH₂CN H H H CF₃ H NMe N 0 N 367 CH₂CycBu H H H CF₃ H NMe N 0 N 368 CF₂Br H H H CF₃ H NMe N 0 N 369 Et H CF₂H H CF₃ H NMe N 2 N 370 Et H CH₂OH H CF₃ H NMe N 2 N 371 Bu H H H CF₃ H NMe N 2 N 372 CH₂EN H H H CF₃ H NMe N 2 N 373 CH₂tBu H H H CF₃ H NMe N 2 N 374 CH₂CH₂CN H H H CF₃ H NMe N 2 N 375 CH₂CycBu H H H CF₃ H NMe N 2 N

[Table 16]

[Table 17]

[Table 18]

Numbering R¹ R² R³ R⁴ R⁵ R⁶ A¹ A² n Q 426 CH(CH₃)CH₂CH₃ H CF₃ H CF₂CF₃ H NMe N 0 N 427 CH(CH₃)CH₂CH₃ H CF₃ H CF₂CF₃ H NMe N 2 N 428 CH₂CH(CH₃)₂ H CF₃ H CF₂CF₃ H NMe N 0 N 429 CH₂CH(CH₃)₂ H CF₃ H CF₂CF₃ H NMe N 2 N 430 tBu H CF₃ H CF₂CF₃ H NMe N 0 N 431 tBu H CF₃ H CF₂CF₃ H NMe N 2 N 432 CH₂CF₃ H CF₃ H CF₂CF₃ H NMe N 0 N 433 CH₂CF₃ H CF₃ H CF₂CF₃ H NMe N 2 N 434 Et H CF₃ H EN H NMe N 0 N 435 Et H H H CF₃ H NMe CCF₃ 0 N 436 Et H H H SCF₃ H O N 0 N 437 Et H H H SCF₃ H O N 1 N 438 Et H H H SCF₃ H O N 2 N 439 Et H H H S(O)CF₃ H O N 2 N 440 Et H H H S(O)₂CF₃ H O N 2 N 441 Et H H H SCF₃ H O CH 0 N 442 Et H H H SCF₃ H O CH 1 N 443 Et H H H SCF₃ H O CH 2 N 444 Et H H H S(O)CF₃ H O CH 2 N 445 Et H H H S(O)₂CF₃ H O CH 2 N 446 Et H CF₃ H SCF₃ H O N 0 N 447 Et H CF₃ H SCF₃ H O N 1 N 448 Et H CF₃ H SCF₃ H O N 2 N 449 Et H CF₃ H S(O)CF₃ H O N 2 N 450 Et H CF₃ H S(O)₂CF₃ H O N 2 N

[Table 19]

Numbering R¹ R² R³ R⁴ R⁵ R⁶ A¹ A² n Q 451 Et H CF₃ H SCF₃ H O CH 0 N 452 Et H CF₃ H SCF₃ H O CH 1 N 453 Et H CF₃ H SCF₃ H O CH 2 N 454 Et H CF₃ H S(O)CF₃ H O CH 2 N 455 Et H CF₃ H S(O)₂CF₃ H O CH 2 N 456* Et H H H S(O)₂CF₃ H O N(→O) 2 N 457* Et H CF₃ H S(O)₂CF₃ H O N(→O) 2 N 458* Et H H H S(O)₂CF₃ H O N 2 N(→O) 459* Et H H H S(O)₂CF₃ H O CH 2 N(→O) 460* Et H CF₃ H S(O)₂CF₃ H O N 2 N(→O) 461* Et H CF₃ H S(O)₂CF₃ H O CH 2 N(→O) 462 Et H H H CF₂CF₃ H O N 0 N 463 Et H H H CF₂CF₃ H O N 1 N 464 Et H H H CF₂CF₃ H O N 2 N 465 Et H H H CF₂CF₃ H O CH 0 N 466 Et H H H CF₂CF₃ H O CH 1 N 467 Et H H H CF₂CF₃ H O CH 2 N 468 Et H CF₃ H CF₂CF₃ H O N 0 N 469 Et H CF₃ H CF₂CF₃ H O N 1 N 470 Et H CF₃ H CF₂CF₃ H O N 2 N 471 Et H CF₃ H CF₂CF₃ H O CH 0 N 472 Et H CF₃ H CF₂CF₃ H O CH 1 N 473 Et H CF₃ H CF₂CF₃ H O CH 2 N 474 Et H H H S(O)CF₃ H O N 0 N 475 Et H H H S(O)₂CF₃ H O N 0 N

[Table 20]

Numbering R¹ R² R³ R⁴ R⁵ R⁶ A¹ A² n Q 476 Et H H H S(O)CF₃ H O CH 0 N 477 Et H H H S(O)₂CF₃ H O CH 0 N 478 Et H CF₃ H S(O)CF₃ H O N 0 N 479 Et H CF₃ H S(O)₂CF₃ H O N 0 N 480 Et H CF₃ H S(O)CF₃ H O CH 0 N 481 Et H CF₃ H S(O)₂CF₃ H O CH 0 N

Herein, the symbol "*" in the compounds of the present invention as listed in the above-mentioned [Table 1] to [Table 20] represents an N-oxide. Specific examples thereof include the following.

In the above-mentioned [Table 1] to [Table 20], Me represents methyl, Et represents ethyl, Pr represents propyl, Bu represents butyl, tBu represents tert-butyl, iPr represents isopropyl, CycPr represents Cyclopropyl, and CycBu represents cyclobutyl.

These compounds can be prepared according to the methods described in the WO 2013/018928 pamphlet or the WO 2014/104407 pamphlet. Regarding some of them, the preparation methods thereof are described below.

Preparation Example 1 (1)

2-(3-Ethylthio-pyridin-2-yl)-6-iodo-3-methyl-3H-imidazo[4,5-b]pyridine 1.1 g, copper iodide (1) 160 mg, sulfuric acid A mixture of 2.7 g of sodium 9-hydrate and 10 mL of N,N-dimethylformamide (hereinafter, referred to as DMF) was stirred at 110° C. for 5 hours. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain a compound represented by the formula mentioned below:

(hereinafter, referred to as compound (1-1)) 710 mg.

¹ H-NMR (DMSO-D ₆ )δ: 8.56-8.55(2H,m), 8.53-8.50(2H,m), 8.38-8.36(2H,m), 8.04(2H,d), 7.61-7.56( 2H,m), 3.87(6H,brs), 3.00(4H,q), 1.23-1.16(6H,m).

Preparation Example 1 (2)

A mixture of 710 mg of compound (1-1) and 12 mL of DMF was cooled to -60°C, and 10 g of trifluoroiodomethane was added thereto. At -40°C, 1.2 mL of tetrakis(dimethylamino)ethylene was added dropwise to the mixture. The mixture was warmed to -10°C and stirred at -10°C for 5 hours. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 2-(3-ethylsulfanyl-pyridin-2-yl)-3-methyl-6-trifluoromethylsulfanyl-3H-imidazo[4,5-b]pyridine (hereinafter, referred to as "the present compound 13") 530 mg.

¹ H-NMR (CDCl ₃ )δ: 8.67(1H,d), 8.52(1H,dd), 8.46(1H,d), 7.79(1H,dd), 7.39(1H,dd), 4.03(3H,s ), 2.97(2H,q), 1.36(3H,t).

Preparation Example 2

A mixture of 200 mg of the present compound 13, 230 mg of m-chloroperbenzoic acid (purity of 65% or more) and 10 mL of chloroform was stirred under ice-cooling for 5 hours. To the reaction mixture was added saturated aqueous sodium bicarbonate solution and the mixture was extracted with chloroform. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 2-(3-ethylsulfanyl-pyridin-2-yl)-3-methyl-6-trifluoromethylsulfanyl-3H-imidazo[4,5-b]pyridine (hereinafter, referred to as "the present compound 14") 89 mg and 2-(3-ethylsulfonyl-pyridin-2-yl)-3-methyl-6-trifluoromethylthio-3H-imidazo[ 4,5-b]pyridine (hereinafter, referred to as "the present compound 15") 130 mg.

Compound 14 of the present invention

¹ H-NMR (CDCl ₃ )δ: 8.87-8.83(1H,m), 8.73-8,64(2H,m), 8.41(1H,d), 7.72-7.66(1H,m), 4.34(3H, s), 3.72-3.62(1H,m), 3.17-3.05(1H,m), 1.47(3H,t).

Compound 15 of the present invention

¹ H-NMR (CDCl ₃ )δ: 9.01-8.98(1H,m), 8.71(1H,d), 8.55-8.52(1H,m), 8.39(1H,d), 7.72(1H,dd), 3.90 -3.81(5H,m), 1.36(3H,t).

Preparation Example 3(1)

To a mixture of 3-chloro-2-cyanopyridine 1.39 g, ethanethiol 0.9 mL and DMF 10 mL was added 0.52 g of sodium hydride (60%, oily matter) under ice cooling, and the mixture was stirred at room temperature for 1 hour. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate solution and saturated brine, and the mixture was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 1.52 g of 2-cyano-3-ethylthiopyridine.

¹ H-NMR (CDCl ₃ ) δ: 8.49 (1H, dd), 7.75 (1 H, dd), 7.43 (1 H, dd), 3.06 (2H, q), 1.38 (3H, t).

Preparation Example 3(2)

To a mixture of 15 mL of concentrated sulfuric acid and 5 mL of water was added 1.4 g of 2-cyano-3-ethylthiopyridine, and the mixture was stirred at 130° C. for 2 hours. The reaction mixture was allowed to cool to room temperature, and an aqueous potassium hydroxide solution was added thereto, and the mixture was extracted with ethyl acetate. To the obtained aqueous layer was added concentrated hydrochloric acid, and the mixture was extracted with chloroform, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to obtain 1.15 g of 3-ethylthiopicolinic acid.

¹ H-NMR (CDCl ₃ ) δ: 8.31 (1H,d), 7.75 (1H,d), 7.49 (1H,dd), 2.97 (2H,q), 1.44 (3H,t).

Preparation Example 3(3)

2-Amino-4-(trifluoromethylthio)phenol (prepared by the method described in WO 2009/131237 pamphlet) 1.0 g, 3-ethylthiopicolinic acid 0.87 g, 1-ethyl-3 A mixture of 1.10 g of -(3-dimethylaminopropyl)carbodiimide hydrochloride and 10 mL of chloroform was stirred at room temperature for 30 minutes. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to obtain 3-ethylthio-N-[2-hydroxy-5-(trifluoromethylthio)phenyl]pyridineamide (hereinafter, referred to as "Compound 3-3" ) 1.32g.

Compound 3-3

¹ H-NMR (CDCl ₃ )δ: 10.40(1H,brs), 9.63(1H,s), 8.36(1H,dd), 7.75(1H,dd), 7.53(1H,d), 7.45(1H,dd) ), 7.41 (1H, dd), 7.08 (1H, d), 2.97 (2H, q), 1.44 (3H, t).

Preparation Example 3(4)

A mixture of compound 3-3 1.23 g, di-2-methoxyethylazodicarboxylate 1.28 g, triphenylphosphine 1.39 g and tetrahydrofuran 30 mL was stirred at room temperature for 1 hour and at 50°C for 1 hour. The reaction mixture was allowed to cool to room temperature, then concentrated under reduced pressure, water was added thereto, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate solution and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 2-(3-ethylsulfanylpyridin-2-yl)-5-(trifluoromethylsulfanyl)benzo azole (hereinafter, referred to as "the present compound 441") 1.21 g.

¹ H-NMR (CDCl ₃ )δ: 8.59(1H,dd), 8.27(1H,s), 7.78(1H,dd), 7.75-7.69(2H,m), 7.42(1H,dd), 3.07(2H ,q),1.47(3H,t).

Preparation Example 4

To a mixture of the present compound 441 (1.06 g) and 30 mL of chloroform was added 1.47 g of m-chloroperbenzoic acid (purity 65% or higher) under ice cooling, and the mixture was stirred at room temperature for 6 hours. To the reaction mixture was added a 10% aqueous sodium sulfite solution, and the mixture was extracted with chloroform. The organic layer was washed with saturated aqueous sodium bicarbonate solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 2-(3-ethylsulfonylpyridin-2-yl)-5-(trifluoromethylthio)benzol azole (hereinafter, referred to as "the present compound 443") 0.87 g and 2-(3-ethylsulfonylpyridin-2-yl)-5-(trifluoromethylsulfinyl)benzoyl azole (hereinafter, referred to as "the present compound 444") 0.17 g.

Compound 443 of the present invention

¹ H-NMR (CDCl ₃ )δ: 9.03(1H,dd), 8.60(1H,dd), 8.19(1H,d), 7.80-7.71(3H,m), 4.02(2H,q), 1.43(3H ,t).

Compound 444 of the present invention

¹ H-NMR (CDCl ₃ )δ: 9.04(1H,dd), 8.61(1H,dd), 8.35(1H,d), 7.96-7.86(2H,m), 7.77(1H,dd), 4.01(2H ,q),1.44(3H,t).

Preparation Example 5

To a mixture of 0.35 g of the present compound 443 and 8 mL of chloroform was added 0.43 g of m-chloroperbenzoic acid (purity 65% or higher) under ice cooling, and the mixture was stirred at 40°C for 6 hours. The reaction mixture was allowed to cool to room temperature, and thereto was added a 10% aqueous sodium sulfite solution, and the mixture was extracted with chloroform. The organic layer was washed with saturated aqueous sodium bicarbonate solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. To the obtained residue were added 4 mL of acetonitrile, 30 mg of sodium tungstate dihydrate, and 4 mL of a hydrogen peroxide solution (30%), and the mixture was stirred at 80°C for 6 hours. The reaction mixture was allowed to cool to room temperature, and water was added thereto, and the precipitated solid was collected by filtration, and to the filtrate was added a 10% aqueous sodium sulfite solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 2-(3-ethylsulfonylpyridin-2-yl)-5-(trifluoromethylsulfonyl)benzol azole (hereinafter, referred to as "the present compound 445") 0.35 g.

Compound 445 of the present invention

¹ H-NMR (CDCl ₃ )δ: 9.05(1H,dd), 8.61(1H,dd), 8.59(1H,d), 8.17(1H,dd), 7.96(1H,d), 7.80(1H,dd) ), 3.98 (2H, q), 1.45 (3H, t).

Triflumezopyrim used in the present invention is in the form of a mesoionic inner salt, and is represented by the following six structural formulas.

Triflumezopyrim can be prepared according to the method described in the pamphlet WO 2012/092115, and in this document it is described as 2-hydroxy-4-oxo-1-(5-pyrimidinylmethyl)-3-[ 3-(Trifluoromethyl)phenyl]-4H-pyrido[1,2-a]pyridine Intermolecular salt.

In a certain embodiment, examples of compositions of the present invention include the following.

A composition for controlling pests, comprising a compound represented by formula (1), wherein A ¹ represents -NMe-, an oxygen atom or a sulfur atom, and A ² represents =N-, =N(→O)- or =CH-, R ¹ represents a C1-C6 alkyl group optionally having one or more halogen atoms, R ² and R ⁴ each represent a hydrogen atom, and R ³ represents C1 optionally having one or more halogen atoms -C3 alkyl or hydrogen atom, R ⁵ represents C1-C3 alkyl optionally having one or more halogen atoms, -OR ¹⁰ or -S(O) _m R ¹⁰ , R ⁶ represents -NR ¹⁰ R ¹¹ or a hydrogen atom, and R ¹⁰ and R ¹¹ independently of each other represent a C1-C3 alkyl group optionally having one or more halogen atoms; and triflumezopyrim.

A composition for controlling pests, comprising a compound represented by formula (1), wherein A ¹ represents -NMe- or an oxygen atom, and A 2 represents =N-, =N(→O)- or =CH- , R ¹ represents a C1-C6 alkyl group optionally having one or more halogen atoms, R ² and R ⁴ each represent a hydrogen atom, and R ³ represents a C1-C3 alkyl group optionally having one or more halogen atoms or a hydrogen atom, R ⁵ represents a C1-C3 alkyl optionally having one or more halogen atoms, -OR ¹⁰ or -S(O) _m R ¹⁰ , R ⁶ represents -NR ¹⁰ R ¹¹ or a hydrogen atom, and R ¹⁰ and R ¹¹ independently of one another represent a C1-C3 alkyl group optionally having one or more halogen atoms; and triflumezopyrim.

A composition for controlling pests, comprising a compound represented by formula (1), wherein A ¹ represents -NMe- or an oxygen atom, and A ² represents =N-, =N(→O)- or =CH -, R ¹ represents a C1-C6 alkyl group, R ² , R ⁴ and R ⁶ each represent a hydrogen atom, R ³ represents a C1-C3 alkyl group or a halogen atom optionally having one or more halogen atoms, and R ⁵ represents C1-C3 alkyl optionally having one or more halogen atoms, -OR ¹⁰ or -S(O) _m R ¹⁰ , and R ¹⁰ represents C1-C3 alkyl optionally having one or more halogen atoms ; and triflumezopyrim.

A composition for controlling pests, comprising a compound represented by formula (1), wherein A ¹ represents -NMe-, A ² represents =N- or =N(→O)-, and R ¹ represents C1- C6 alkyl, R ² , R ⁴ and R ⁶ each represent a hydrogen atom, R ³ represents a C1-C3 alkyl group or a hydrogen atom optionally having one or more halogen atoms, and R ⁵ represents optionally having one or more halogen atoms a C1-C3 alkyl group of halogen atoms or -S(O) _m R ¹⁰ , and R ¹⁰ represents a C1-C3 alkyl group optionally having one or more halogen atoms; and triflumezopyrim.

A composition for controlling pests, comprising a compound represented by formula (1), wherein A ¹ represents an oxygen atom, A ² represents =N-, =N(→O)- or =CH-, R ¹ represents a C1-C6 alkyl group, R ² , R ⁴ and R ⁶ each represent a hydrogen atom, R ³ represents a C1-C3 alkyl group or a hydrogen atom optionally having one or more halogen atoms, and R ⁵ represents an optionally having C1-C3 alkyl of one or more halogen atoms, -OR ¹⁰ or S(O) _m R ¹⁰ , and R ¹⁰ represents C1-C3 alkyl optionally having one or more halogen atoms; and triflumezopyrim.

A composition for controlling pests, comprising a compound represented by formula (1), wherein A ¹ represents an oxygen atom, A ² represents =N- or =N(→O)-, and R ¹ represents optionally A C1-C6 alkyl group having one or more halogen atoms, R ² , R ³ , R ⁴ and R ⁶ each represent a hydrogen atom, and R ⁵ represents a C1-C3 alkyl group optionally having one or more halogen atoms or -S(O) _m R ¹⁰ , and R ¹⁰ represents a C1-C3 alkyl group optionally having one or more halogen atoms; and triflumezopyrim.

A composition for controlling pests, comprising a compound represented by formula (1), wherein A ¹ represents an oxygen atom, A ² represents =N-, R ¹ represents a C1-C6 alkyl group, R ² , R ³ , R ⁴ and R ⁶ each represent a hydrogen atom, R ⁵ represents a C1-C3 alkyl group optionally having one or more halogen atoms or -S(O) _m R ¹⁰ , and R ¹⁰ represents optionally having one or more halogen atoms C1-C3 alkyl groups of multiple halogen atoms; and triflumezopyrim.

A composition for controlling pests, comprising a compound represented by formula (1), wherein A ¹ represents an oxygen atom, A ² represents =CH-, and R ¹ represents a compound optionally having one or more halogen atoms C1-C6 alkyl, R ² , R ³ , R ⁴ and R ⁶ each represent a hydrogen atom, R ⁵ represents C1-C3 alkyl optionally having one or more halogen atoms or -S(O) _m R ¹⁰ , and R ¹⁰ represents a C1-C3 alkyl group optionally having one or more halogen atoms; and triflumezopyrim.

A composition for controlling pests, comprising a compound represented by formula (1), wherein A ¹ represents an oxygen atom, A ² represents =CH-, R ¹ represents a C1-C6 alkyl group, R ² , R ³ , R ⁴ and R ⁶ each represent a hydrogen atom, R ⁵ represents a C1-C3 alkyl group optionally having one or more halogen atoms or -S(O) _m R ¹⁰ , and R ¹⁰ represents optionally having one or more halogen atoms C1-C3 alkyl groups of multiple halogen atoms; and triflumezopyrim.

A composition for controlling pests, comprising a compound represented by formula (1), wherein R ¹ represents a C1-C6 alkyl group optionally having one or more atoms or groups selected from the Y group ( Group Y: a group consisting of a C3-C6 cycloalkyl group optionally having one or more halogen atoms, and a halogen atom), R ² and R ⁴ each represent a hydrogen atom, and R ³ represents optionally having one or more C1-C3 alkyl, -C(OR ¹⁰ ) ₃ , halogen atom or hydrogen atom of halogen atoms, R ⁵ represents C1-C3 alkyl optionally having one or more halogen atoms, -OR ¹⁰ , -S (O) _m R ¹⁰ , -CO ₂ R ¹⁰ , -SF ₅ or a halogen atom, R ⁶ represents -OR ¹⁰ , -NR ¹⁰ R ¹¹ , -CO ₂ R ¹⁰ , -C(O)NR ¹⁰ R ¹¹ , - OC(O)R ¹⁰ , a cyano group, a halogen atom or a hydrogen atom, R ⁷ represents a C1-C6 alkyl group optionally having one or more halogen atoms, -CH ₂ CO ₂ R ¹⁰ , a C3-C6 cycloalkyl group or a hydrogen atom, R ⁸ represents a C1-C3 alkyl group optionally having one or more halogen atoms, -OR ¹⁰ , -S(O) _m R ¹⁰ , a cyano group, a halogen atom or a hydrogen atom, R ¹⁰ and R ¹¹ independently of each other represent a C1-C3 alkyl group or a hydrogen atom optionally with one or more halogen atoms (provided that in -S(O) _m R ¹⁰ , when m is 1 or 2, R ¹⁰ is not represents a hydrogen atom); and triflumezopyrim.

A composition for controlling pests, comprising a compound represented by formula (1), wherein R ¹ represents a C1-C3 alkyl group optionally having one or more halogen atoms, and R ² and R ⁴ each represent A hydrogen atom, R ³ represents a C1-C3 alkyl group optionally having one or more halogen atoms, -C(OR ¹⁰ ) ₃ , a halogen atom or a hydrogen atom, R ⁵ represents optionally having one or more halogen atoms C1-C3 alkyl, -OR ¹⁰ , -S(O) _m R ¹⁰ or halogen atom, R ⁶ represents cyano, -NR ¹⁰ R ¹¹ , halogen atom or hydrogen atom, R ⁷ represents optionally having one or C1-C6 alkyl of a plurality of halogen atoms, R ⁸ represents -S(O) _m R ¹⁰ , cyano group, halogen atom or hydrogen atom, and R ¹⁰ and R ¹¹ each independently of each other represent cyano group, halogen atom or hydrogen atom, and R ¹⁰ and R ¹¹ each independently of one another represent a C1-C3 alkyl group optionally having one or more halogen atoms; and triflumezopyrim.

A composition for controlling pests, comprising a compound represented by formula (1), wherein R ¹ represents an ethyl group, R ² and R ⁴ each represent a hydrogen atom, and R ³ represents optionally having one or more C1-C3 alkyl group, -C(OR ¹⁰ ) ₃ , halogen atom or hydrogen atom of halogen atom, R ⁵ represents C1-C3 halogenated alkyl group, -OR ²⁰ , -S(O) _m R ²⁰ or halogen atom (the R ²⁰ represents a C1-C3 haloalkyl group), R ⁶ represents a cyano group, -NR ¹⁰ R ¹¹ , a halogen atom or a hydrogen atom, R ⁷ represents a C1-C6 alkyl group optionally having one or more halogen atoms, and R ⁸ represents -S(O) _m R ¹⁰ , a cyano group, a halogen atom or a hydrogen atom, and R ¹⁰ and R ¹¹ independently of each other represent a C1-C3 alkyl group optionally having one or more halogen atoms; and triflumezopyrim.

A composition for controlling pests, comprising a compound represented by formula (1), wherein A ¹ represents -NR ⁷ -; and triflumezopyrim.

A composition for controlling pests, comprising a compound represented by formula (1), wherein A ¹ represents an oxygen atom; and triflumezopyrim.

A composition for controlling pests, comprising a compound represented by formula (1), wherein A ¹ represents -NR ⁷ -, R ¹ represents a C1-C3 alkyl group, and R ² and R ⁴ each represent a hydrogen atom, R ³ represents a C1-C3 alkyl group optionally having one or more halogen atoms R ³ represents a C1-C3 alkyl group optionally having one or more halogen atoms, -C(OR ¹⁰ ) ₃ , a halogen atom or Hydrogen atom, R ⁵ represents C1-C3 haloalkyl, -OR ²⁰ , -S(O) _m R ²⁰ or halogen atom, R ⁶ represents cyano group, -NR ¹⁰ R ¹¹ , halogen atom or hydrogen atom, R ⁷ represents any C1-C6 alkyl optionally having one or more halogen atoms, R ⁸ represents -S(O) _m R ¹⁰ , cyano, halogen atom or hydrogen atom, and R ¹⁰ and R ¹¹ independently of each other represent optionally a C1-C3 alkyl group having one or more halogen atoms, and R ²⁰ represents a C1-C3 haloalkyl group; and triflumezopyrim.

A composition for controlling pests, comprising a compound represented by formula (1), wherein A ¹ represents an oxygen atom, R ¹ represents an ethyl group, R ² , R ⁴ and R ⁶ each represent a hydrogen atom, and R ³ represents a C1-C3 alkyl group optionally having one or more halogen atoms, -C(OR ¹⁰ ) ₃ , a halogen atom or a hydrogen atom, and R ⁵ represents a C1-C3 haloalkyl group, -OR ²⁰ , -S(O) _m R ²⁰ or a halogen atom, R ⁸ represents -S(O) _m R ¹⁰ , a cyano group, a halogen atom or a hydrogen atom, R ¹⁰ represents a C1-C3 alkyl group optionally having one or more halogen atoms, and R ²⁰ represents C1-C3 haloalkyl; and triflumezopyrim.

A composition for controlling pests, comprising a compound represented by formula (1), wherein A ¹ represents an oxygen atom, R ¹ represents an ethyl group, R ² , R ⁴ and R ⁶ each represent a hydrogen atom, and R ³ represents a halogen atom or a hydrogen atom, R ⁵ represents a C1-C3 perfluoroalkyl group, -OR ³⁰ or -S(O)mR ³⁰ , R ³⁰ represents a C1-C3 perfluoroalkyl group, and R ⁸ represents a halogen atom or a hydrogen atom ; and triflumezopyrim.

The composition of the present invention may simply be a mixture of the compound of the present invention and triflumezopyrim, however, it is generally prepared by admixing the compound of the present invention and triflumezopyrim with an inert carrier, and if desired, adding surfactants and other auxiliaries for formulation, It can be formulated into oil solutions, emulsifiable concentrates, flowables, wettable powders, granular wettable powders, dust formulations, granules and the like.

Moreover, the composition for controlling pests formulated above can be used by itself or by adding other inert ingredients.

In the composition of the present invention, the total amount of the compound of the present invention and triflumezopyrim is generally in the range of 0.1% to 100% by weight, preferably in the range of 0.2% to 90% by weight, and more preferably in the range of 1 to 80% by weight %In the range.

Examples of inert carriers used in the formulation include solid carriers and liquid carriers. Examples of solid carriers include fine powders and granules of clays (eg, kaolin, diatomaceous earth, bentonite, Fubasami clay, or acid clay), synthetic hydrated silica, talc, ceramics, other inorganic minerals (eg, sericite, quartz) , sulfur, activated carbon, calcium carbonate or hydrated silica) or chemical fertilizers (for example, ammonium sulfate, ammonium phosphate, ammonium nitrate, urea or ammonium chloride), etc.; and synthetic resins (for example, polyester resins such as polypropylene, Acrylonitrile, polymethylmethacrylate, and polyethylene terephthalate; nylon resins (eg, nylon-6, nylon-11, and nylon-66); polyamide resins; polyvinyl chloride, polyvinylidene chloride Ethylene, vinyl chloride-propylene copolymer, etc.

Examples of liquid carriers include water, alcohols (eg, methanol, ethanol, isopropanol, butanol, hexanol, benzyl alcohol, ethylene glycol, propylene glycol, or phenoxyethanol); ketones (eg, acetone, methyl ethyl ketone, or cyclohexane) ketones); aromatic hydrocarbons (eg, toluene, xylene, ethylbenzene, dodecylbenzene, phenylxylylethane, or methylnaphthalene); aliphatic hydrocarbons (eg, hexane, cyclohexane, kerosene) or light oil); esters (for example, ethyl acetate, butyl acetate, isopropyl myristate, ethyl oleate, diisopropyl adipate, diisobutyl adipate, or ethyl propylene glycol monomethyl ether esters); nitriles (eg, acetonitrile or isobutyronitrile); ethers (eg, diisopropyl ether, 1,4-diisopropyl ether) alkane, ethylene glycol dimethyl ether, diglyme, dipropylene glycol monomethyl ether, or 3-methoxy-3-methyl-1-butanol); amides (eg, N,N-dimethyl formamide or N,N-dimethylacetamide); halogenated hydrocarbons (eg, dichloromethane, trichloroethane, or carbon tetrachloride); sulfoxides (eg, dimethyl sulfoxide); propylene carbonate; and vegetable oils (eg, soybean oil or cottonseed oil).

Examples of surfactants include nonionic surfactants such as polyoxyethylated alkyl ethers, polyoxyethylated alkyl aryl ethers, and polyethylene glycol fatty acid esters; and anionic surfactants such as alkyl sulfonic acids salts, alkylbenzene sulfonates and alkyl sulfates.

Examples of other adjuvants for formulation include binders, dispersants, colorants and stabilizers. Specific examples include casein, gelatin, polysaccharides (eg, starch, gum arabic, cellulose derivatives, and alginic acid), bentonite, water-soluble synthetic polymers (eg, polyvinyl alcohol, polyvinylpyrrolidone, and polyacrylic acid), PAP ( Acid isopropyl phosphate), BHT (2,6-di-tert-butyl-4-cresol), BHA (2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4- mixture of methoxyphenols).

The method for controlling pests of the present invention is carried out by applying an effective amount of the composition of the present invention to pests or habitats, plants, soils, and the like where pests live. In the method for controlling pests of the present invention, the composition of the present invention is usually applied in the form of an agent for controlling pests to which the composition of the present invention is formulated.

Specific examples of applying the composition of the present invention include application to stems and leaves, flowers, seedlings or ears (plants); application to soil before planting plants or soil after planting plants (soil for growing plants); application to plants Seeds (eg, seed sterilization, seed soaking, or seed coating) or bulbs such as seed tubers are applied. Furthermore, the compounds of the present invention and triflumezopyrim can be applied separately, and, for example, either one of the compounds of the present invention and triflumezopyrim is deposited to a seed or bulb of a plant and then the other is applied to said seed or said bulb of the plant , or the soil used to grow said seeds or said bulbs of the plant before or after planting.

Specific examples of the method for application to the stem and leaves of plants, flowers, seedlings, ears include methods for application to the surface of plants such as foliar application and trunk application, and methods for application at the time of flowering (including before flowering) , during and after flowering) to flowers or whole plants, and methods for application to ears or whole plants during the grain germination season.

Also, examples of the method with application to soil before or after planting plants (soil for growing plants) include applying the composition of the present invention to crops to be protected from damage such as being eaten by pests and methods of controlling pests that eat plants by absorbing and transferring the compositions of the present invention from the roots and/or underground stems to the interior of the plant.

Specific examples of the application treatments include treatment of planting holes (spraying into the planting holes, soil mixing after the treatment of the planting holes), treatment of the bottom of plants (spraying of the bottom of plants, soil mixing after the treatment of the bottom of plants, Irrigation of plant bases, treatment of plant substrates at late seedling stage), in-furrow treatment (spraying into furrow, soil mixing after in-furrow treatment), treatment of planting rows (spraying of planting rows, Soil mix after planting row treatment, spraying planting row during growing season), treatment of planting row at sowing (soil mixing after planting row spraying at sowing, soil mix after planting row treatment at sowing), Spreading treatments (overall soil surface spray, soil mixing after spreading treatments), treatments to lateral rows, treatments to water surfaces (applications to water surfaces, applications to water surfaces after irrigation), other soil sprays Treatment (spraying granules on foliage during growing season, spraying under canopy or around tree trunks, spraying on soil surface, mixing with surface soil, spraying into seeding holes, spraying on the ground in furrows, Spray between plants), other irrigation treatments (soil irrigation, irrigation at seedling stage, solution injection, partial irrigation of plants just above the ground, solution drip irrigation, chemical irrigation), nursery box treatments (spray to nursery boxes, nursery box irrigation, irrigation with chemical solution into the nursery box), nursery tray treatment (spray the nursery tray, irrigate the nursery tray, and irrigate the nursery tray with a chemical solution), seedbed treatment (spray the seedbed, irrigate the seedbed, irrigate the nursery tray) seedling bed spraying, soaking seedlings), seedbed soil incorporation treatments (mixing with seedbed soil, mixing with seedbed soil before sowing, spraying before mulching with soil at sowing, mixing with mulching soil, and other treatments (with culturing soil) Mixing, plowing under, mixing with surface soil, mixing with soil from where raindrops fell, treatment of planting site, spraying granules on flower clusters, mixing with slurry fertilizer).

Examples of application to the seed or bulb of a plant can also be carried out by applying the composition of the present invention to the seed or bulb of the plant. The seeds of plants described herein refer to the seeds of plants in a state prior to sowing into soil or a medium for cultivating seeds, and the bulbs described herein refer to seeds that are in a state before being sown into soil or a medium for cultivating seeds Discoid stems, bulbs, rhizomes, tubers, tubers, seed tubers and tuberous roots of plants in the previous state. Examples of methods for controlling pests by applying the compositions of the present invention to seeds or bulbs of plants include applying the compositions of the present invention directly to the seeds of plants to be protected from damage such as ingested by pests or A method in a bulb; and a method of controlling seed-ingesting pests by using the composition of the present invention near the seed or bulb of a plant; and by infiltrating and transferring the composition of the present invention from the seed or bulb of a plant to A method of controlling the interior of a plant body against a pest ingesting a plant. Examples of the method of applying the composition of the present invention to seeds or bulbs of plants include spraying treatment, spraying treatment, soaking treatment, dipping treatment, coating treatment, film coating treatment and particle coating treatment.

When the composition of the present invention is used for controlling pests, the application dose may vary widely depending on the application time, application site, application mode, and the like. The total amount of the compound of the present invention and triflumezopyrim is generally in the range of 1 to 10,000 g/10,000 m ² . When the compositions of the present invention are formulated as emulsifiable concentrates, wettable powders, flowable formulations, etc., the compounds of the present invention and triflumezopyrim are usually applied by diluting them with water so that the total concentration of the compounds of the present invention and triflumezopyrim is in the range of 0.01 to 10,000 ppm Inside. In the case of granular formulations or dust-like formulations and the like, these formulations are usually used as they are without their dilution.

Also, when the composition of the present invention is applied to rice, the composition of the present invention can be used by a nursery box treatment. The time of application of the composition of the present invention by the nursery box treatment may be from the time of sowing to the time of transplantation. Furthermore, the composition of the present invention can be used for direct seeding cultivation or transplantation cultivation of rice. When the composition of the present invention is used for direct sowing cultivation of rice, the composition of the present invention may be used before direct sowing on irrigated paddy fields, after direct sowing on irrigated paddy fields, before direct sowing on dry paddy fields, or at The application is applied directly after sowing on dry paddy fields, and can also be from before sowing to 21 days after sowing. When the composition of the present invention is used for transplanting cultivation of rice, the rice may be after transplanting, and the time of application may be from before transplanting to 21 days after transplanting.

Examples of pests for which the compositions of the present invention have some efficacy include noxious arthropods such as noxious insects and noxious mites. Specific examples of the harmful organisms include the following.

Hemipteran pests:

Delphacidae (for example, Laodelphax striatellus, Nilaparvata lugens or Sogatella furcifera),

Deltocephalidae (for example, Nephotettix cincticeps, Nephotettix virescens, Empoasca onukii),

Aphididae (eg, cotton aphid (Aphis gossypii), green peach aphid (Myzus persicae), cabbage aphid (Brevicoryne brassicae), spiraea aphid (Aphis spiraecola), potato aphid (Macrosiphumeuphorbiae), potato furrow Aulacorthum solani, Rhopalosiphum padi, Toxoptera citricidus or Hyalopterus pruni),

Pentatomidae (eg, Nezara antennata, Riptortus clavetus, Riptortus clavetus, Leptocorisa chinensis, Eysarcoris parvus) or Halyomorpha mista),

Family Aleyrodidae (eg, Trialeurodes vaporariorum, Bemisia tabaci, Dialeurodes citri, Aleurocanthus spiniferus).

Lepidoptera pests:

Pyralidae (eg, Chilo suppressalis, Tryporyzaincertulas, Cnaphalocrocis medinalis, Notarchaderogata, Plodia interpunctella), Asian corn borer (Ostrinia furnacalis), cabbage wild borer (Hellula undalis) or blue grass borer moth (Pediasia teterrellus),

Noctuidae (eg, Spodoptera litura, Spodoptera exigua, armyworm (Pseudaletia separata), cabbage armyworm (Mamestra brassicae), small cutworm (Agrotis ipsilon), black Plusia nigrisigna, Trichoplusia spp., Heliothis spp. or Helicoverpa spp.),

Pieridae (for example, Pieris rapae),

Tortricidae (e.g., Grapolita molesta, Leguminivora glycinivorella, Matsumuraeses azukivora, Adoxophyes orana fasciata) Adoxophyes honmai.), tea long roll moth (Homonamagnanima), apple yellow roll moth (Archips fuscocupreanus) or apple peel moth (Cydiapomonella)),

Gracillariidae (for example, Caloptilia theivora or Phyllonorycter ringoneella),

Carposinidae (for example, Carposina niponensis),

Lyonetiidae (for example, Lyonetia spp.),

Lymantriidae (for example, Lymantria spp. or Euproctisspp.),

Yponomeutidae (for example, Plutella xylostella),

Gelechiidae (for example, Pectinophora gossypiella or Phthorimaea operculella),

Arctiidae (for example, Hyphantria cunea);

Tinea (eg, Tinea translucens).

Pests of the order Thysanoptera:

Thysanopterae (for example, Frankliniella occidentalis, Thrips parmi, Scirtothrips dorsalis, Thrips tabaci, or Thrips Frankliniella intonsa)).

Diptera pests:

Anthomyiidae (for example, Delia platura or Deliaantiqua),

Agromyzidae (for example, Agromyza oryzae, Hydrellia griseola, Liriomyza sativae, Liriomyzatrifolii, or Liriomyzatrifolii) Chromatomyia horticola)),

Chloropidae (for example, Chlorops oryzae),

Tephritidae (for example, Dacus cucurbitae or Ceratitis capitata), and

Drosophilidae.

Coleoptera pests:

Chrysomelidae (for example, Diabrotica virgiferavirgifera, Diabrotica undecimpunctata howardi),

Scarabaeidae (for example, Anomala cuprea, Anomala rufocuprea, or Popillia japonica),

Curculionidae (for example, Sitophilus zeamais, Lissorhoptrus oryzophilus, Echinocnemus squameus, Anthonomus grandis or Sphenophorus venatus),

Tenebrionidae (for example, Tenebrio molitor or Tribolium castaneum),

Chrysomelidae (for example, Oulema oryzae, Aulacophora femoralis, Phyllotreta striolata or potato beetle (Leptinotarsa decemlineata)),

Epilachna (eg, Epilachnavigintioctopunctata),

of the family Scolytidae (for example, Lyctus brunneus or Tomicuspiniperda),

Bostrichidae,

Spider family (Ptinidae),

Cerambycidae (for example, Anoplophora malasiaca),

Elateridae (Agriotes spp. or Limonius spp.), and

Paederus fuscipes.

The above-mentioned pests also include pest populations that have acquired resistance to conventional agents, and therefore the compositions of the present invention are effective against such resistant populations.

Examples of plants to which the composition of the present invention may be applied include the following.

Crops: corn, rice, wheat, barley, rye, oats, sorghum, cotton, soybean, peanut, buckwheat, sugar beet, rapeseed, sunflower, sugarcane and tobacco, etc.;

Vegetables: nightshade vegetables (eggplant, tomatoes, bell peppers, peppers and potatoes, etc.), gourd vegetables (cucumber, pumpkin, green zucchini, watermelon, melon and pumpkin, etc.), cruciferous vegetables (Japanese radish, white radish, etc.) , horseradish, kohlrabi, Chinese cabbage, cabbage, mustard greens, broccoli and cauliflower, etc.), Compositae vegetables (burdock, chrysanthemum, artichoke and lettuce, etc.), Liliaceae vegetables (green onions, onions, garlic and asparagus), Umbelliferae vegetables (carrot, parsley, celery and parsnips, etc.), Chenopodiaceae vegetables (spinach and chard, etc.), labiata vegetables (perilla, mint and basil, etc.), strawberries, sweet potatoes, Glutinous rice yam and taro, etc.;

flowering plant;

foliage plants;

lawn grass;

Fruits: Pears (apples, pears, Japanese pears, papaya and quince, etc.), stone fruits (peaches, plums, peach plums, Japanese plums (Prunus mume), cherries, apricots and plums, etc.), citrus fruits (Wonshu, tangerine, lemon, lemon and grapefruit, etc.), nuts (chestnut, walnut, hazel, almond, pistachio, cashew and macadamia, etc.), berries (bilberry, cranberry, blackberry, etc.) and raspberries, etc.), grapes, Japanese persimmons, olives, Japanese plum, bananas, coffee, dates and coconuts, etc.; and

Trees other than fruit trees: tea, mulberry, ornamental plants, street trees (ash, birch, ash, eucalyptus, ginkgo (ginkgobiloba), lilac, maple, oak (quercus), poplar, redbud, liquidambar formosana), sycamore, zelkova, Japanese cedar (Thuja standishii), fir, Japanese hemlock, juniper, pine, spruce and yew (Taxuscuspidate), etc.

The plants described above may be plants propagated by hybridization techniques.

That is, plants propagated by hybridization techniques are plants with heterosis (generally, for example, which results in enhanced yield potential and improved resistance to biotic and abiotic stress factors).

The aforementioned "plants" may include plants to which resistance has been conferred by genetic recombination.

For example, the plants described above also include plants having resistance to herbicides, including HPPD inhibitors such as Isoxaflutole; ALS inhibitors such as imazethapyr and thifensulfuron methyl; EPSP inhibitors; glutamine synthase inhibitors; bromoxynil; dicamba, etc., The resistance is conferred by classical propagation methods or genetic modification techniques.

The above-mentioned plants may include plants that have been made capable of synthesizing selective toxins and the like (eg, Bacillus spp.), produced by using genetic modification techniques.

In addition, the above-mentioned plants include lines having two or more types of characteristics associated with the above-mentioned herbicide resistance, pest resistance, disease resistance, etc. (the characteristics are imparted using classical propagation techniques or genetic modification techniques) , and lines having properties possessed by two or more types of maternal lines (the properties are conferred by crossing genetically modified plants with the same or different types of properties). Examples of such plants include Smart stax (registered trademark).

In the compositions of the present invention, the ratio of the compound of the present invention to triflumezopyrim is generally in the range of 100:1 to 1:100, and preferably in the range of 10:1 to 1:10, by weight.

The composition of the present invention may also comprise one or more compounds selected from group (A) as mentioned below.

Group (A): Group consisting of the following compounds: clothianidin, dinotefuran, thiamethoxam, imidacloprid, nitenpyram, thiacloprid ( thiacloprid), fipronil, ethiprole, etofenprox, silafluofen, chlorantraniliprole, cyantraniliprole, Cartap, flupyradifurone, pymetrozine, isotianil, azoxystrobin, orysastrobin, probenazole ), tiadinil, tricyclazole, pyroquilon, diclocymet, ferimzone, phthalide, kasugamycin hydrochloride kasugamycin hydrochloride hydrate, tebufloquin, pencycuron, validamycin, hexaconazole, flutolanil, carpropamid, flupirtine Furametpyr, penflufen and tolprocarb.

Examples of combinations include the following.

A combination of "any one of compounds 1 to 481 of the present invention", triflumezopyrim and isotianil;

"Any one of Compounds 1 to 481 of the present invention", a combination of triflumezopyrim and orysastrobin;

"Any one of Compounds 1 to 481 of the present invention", a combination of triflumezopyrim and probenazole;

"Any one of Compounds 1 to 481 of the present invention", a combination of triflumezopyrim and tricyclazole;

"Any one of Compounds 1 to 481 of the present invention", a combination of triflumezopyrim and diclocymet;

"Any one of Compounds 1 to 481 of the present invention", a combination of triflumezopyrim and carpropamid;

"Any one of Compounds 1 to 481 of the present invention", a combination of triflumezopyrim and tiadinil;

"Any one of Compounds 1 to 481 of the present invention", a combination of triflumezopyrim and pyroquilon;

A combination of "any one of Compounds 1 to 481 of the present invention", triflumezopyrim and tolprocarb;

"Any one of Compounds 1 to 481 of the present invention", a combination of triflumezopyrim and furametpyr;

A combination of "any one of Compounds 1 to 481 of the present invention", triflumezopyrim and penflufen;

"Any one of Compounds 1 to 481 of the present invention", a combination of triflumezopyrim, isotianil and furametpyr;

"Any one of Compounds 1 to 481 of the present invention", a combination of triflumezopyrim, isotianil and penflufen;

"Any one of Compounds 1 to 481 of the present invention", a combination of triflumezopyrim, probenazole and furametpyr;

"Any one of Compounds 1 to 481 of the present invention", a combination of triflumezopyrim, probenazole and penflufen;

"Any one of Compounds 1 to 481 of the present invention", a combination of triflumezopyrim, tricyclazole and furametpyr;

"Any one of Compounds 1 to 481 of the present invention", a combination of triflumezopyrim, tricyclazole and penflufen;

"Any one of Compounds 1 to 481 of the present invention", a combination of triflumezopyrim, tiadinil and furametpyr;

"Any one of the compounds 1 to 481 of the present invention", a combination of triflumezopyrim, tiadinil and penflufen;

"Any one of Compounds 1 to 481 of the present invention", a combination of triflumezopyrim, pyroquilon and furametpyr;

"Any one of Compounds 1 to 481 of the present invention", a combination of triflumezopyrim, pyroquilon and penflufen;

A combination of "any one of Compounds 1 to 481 of the present invention", triflumezopyrim, tolprocarb and furametpyr;

A combination of "any one of compounds 1 to 481 of the present invention", triflumezopyrim, tolprocarb and penflufen;

Example

Hereinafter, the present invention is explained in more detail by using formulation examples and test examples. However, the present invention should not be limited to these Examples. "Parts" means "parts by weight" unless otherwise specified.

First, formulation examples are described.

Formulation Example 1

A mixture of five (5) parts of any one of the compounds 1 to 481 of the present invention, 10 parts of triflumezopyrim, 35 parts of silica and polyoxyethylene alkyl ether sulfate ammonium salt (1:1 by weight) and water were mixed to make 100 parts as a total weight part, followed by fine pulverization using a wet milling method to obtain each formulation.

Formulation Example 2

Ten (10) parts of any one of the compounds 1 to 481 of the present invention, 2 parts of triflumezopyrim, 1.5 parts of sorbitan trioleate, 28 parts of a solution containing 2 parts of polyvinyl alcohol were mixed and utilized After wet milling, a solution containing 0.05 parts of xanthan gum and 0.1 part of magnesium aluminum silicate was added to the mixture to make 90 parts by weight as a total. To the mixture, 10 parts of propylene glycol was added, and the mixture was stirred and mixed to obtain respective formulations.

Formulation Example 3

Ten (10) parts of any one of the compounds 1 to 481 of the present invention, 10 parts of triflumezopyrim, 3 parts of calcium lignosulfonate, 2 parts of sodium lauryl sulfonate and the remaining parts of synthetic hydrated silica well Grind and mix to obtain 100 parts of each wettable powder.

Formulation Example 4

Add one (1) part of any one of compounds 1 to 481 of the present invention, 0.5 part of triflumezopyrim, 1 part of synthetic hydrated silica fine powder, 2 parts of calcium lignosulfonate, 30 parts of bentonite and the remainder kaolin clay and mix. Then, to the mixture, an appropriate amount of water was added, and the mixture was stirred, granulated using a granulator and dried by forced air to obtain 100 parts of each granule preparation.

Formulation Example 5

One hundred (100) parts of 2 parts of any of the present compounds 1 to 481, 0.75 parts of triflumezopyrim, 2 parts of isotianil, 1 part of synthetic hydrated silica, 2 parts of calcium lignosulfonate , a mixture of 30 parts of bentonite and the remaining part of kaolin clay were well ground and mixed, and water was added thereto, and the mixture was well kneaded, granulated and dried to obtain 100 parts of each granule preparation.

Formulation Examples 6 to 15

Each granule formulation was obtained according to the similar procedure of Formulation Example 5, except that the corresponding compounds and their amounts described in [Table A] were used instead of 2 parts of isotianil.

[Table A]

Next, application examples of the composition of the present invention to plant seeds are described.

Application example 1

Each formulation prepared according to the method described in Formulation Example 1 or 2 was prepared in an amount of 200 ml/100 kg of dry sorghum seeds by using a rotary seed treater (seed dresser, manufactured by Hans-Ulrich Hege GmbH). For smear treatment, individual seeds treated were obtained.

Also, 180 g of oxabetrinil or 40 g of fluxofenim was added to 200 mL of each of the preparations obtained in the above-mentioned preparations, and the resulting preparations could be used for smearing treatment in the above-mentioned dried sorghum seeds , to obtain the treated individual seeds.

Application example 2

By using a rotary seed treatment machine (seed dresser, manufactured by Hans-Ulrich Hege GmbH), each formulation prepared according to the method described in Formulation Example 1 or 2 was prepared in an amount of 40 ml/10 kg of dry corn seeds For smear treatment, individual seeds treated were obtained.

Application example 3

Each of the wettable powders prepared according to the method described in Formulation Example 3 was used in the powder coating treatment in an amount of 50 g/10 kg of dry corn seeds to obtain treated individual seeds.

Application example 4

Each formulation prepared according to the method described in Formulation Example 1 or 2 was prepared in an amount of 20 ml/10 kg of dry soybean seeds by using a rotary seed treatment machine (seed dresser, manufactured by Hans-Ulrich Hege GmbH). For smear treatment, individual seeds treated were obtained.

Application example 5

By using a rotary seed treatment machine (seed dresser, manufactured by Hans-Ulrich Hege GmbH), each wettable powder prepared according to the method described in Formulation Example 3 was prepared in an amount of 30 g/10 kg of dry soybean seeds For powder coating treatment, treated individual seeds were obtained.

Application example 6

By using a rotary seed treatment machine (seed dresser, manufactured by Hans-Ulrich Hege GmbH), each formulation prepared according to the method described in Formulation Example 1 or 2 was prepared in an amount of 50 ml/10 kg of dry cotton seeds For smear treatment, individual seeds treated were obtained.

Application example 7

By using a rotary seed treatment machine (seed dresser, manufactured by Hans-Ulrich Hege GmbH), each formulation prepared according to the method described in Formulation Example 1 or 2 was prepared in an amount of 150 ml/10 kg of dried grape seeds For smear treatment, individual seeds treated were obtained.

Application example 8

By using a rotary seed treatment machine (seed dresser, manufactured by Hans-Ulrich Hege GmbH), each formulation prepared according to the method described in Formulation Example 1 or 2 was dried in an amount of 20 ml/10 kg of rice seeds For smear treatment, individual seeds treated were obtained.

Application example 9

By using a rotary seed treatment machine (seed dresser, manufactured by Hans-Ulrich Hege GmbH), each wettable powder prepared according to the method described in Formulation Example 3 was dried in an amount of 60 g/10 kg of rice seeds For powder coating treatment, treated individual seeds were obtained.

Next, the effects of the present invention are shown by the following test examples.

Test Example 1

Dissolve 1 mg of each of the present compounds 3, 15, 19, 20, 48, 50, 72, 81, 85, 99, 130, 421, 444, 445, 464 and 467 or triflumezopyrim into 10 μL of xylene, dimethyl Formamide and a surfactant (trade name: Sorpol 3005X, manufactured by TOHO CHEMICAL INDUSTRY CO.LTD) (4:4:1 (volume ratio)) in a mixed solution. Thereto was added water containing 0.02% (v/v) of a spreading agent (trade name: Sindain, manufactured by Sumitomo Chemical Company, Limited) to obtain products such as [Table 21] to [Table 22] Each of the specified concentrations indicated in to prepare each test chemical solution.

Cotyledon leaf discs (1.5 cm in length) of cucumber (Cucumis sativus) were placed into individual wells of a 24-well plate (manufactured by Becton Dickinson) and 2 wingless adults of cotton aphid (Aphis gossypii) and 8 were released per 1 well. Cotton aphid larvae were sprayed with the test chemical solution at a rate of 20 μL/1 well, which was called a treatment group.

Instead of the test chemical solution, 20 μL of water containing a spreading agent (trade name: Sindain, manufactured by Sumitomo Chemical Co., Ltd.) of 0.02% (v/v) was sprayed into the wells, and this was referred to as an untreated group.

After air drying, the upper part of the microplate was covered with a breathable film sheet (product name: AeraSeal, manufactured by ExcelScientific Inc.), and 5 days after insect release, the number of surviving insects in each well was examined.

For each control value of the treated group or the untreated group, respectively, it was calculated by the following formula.

Formula 1)

Control value (%)={1-(Tai)/(Cai)}×100

where the symbols in the formula represent the following description.

Cai: the number of surviving insects in the untreated group at the time of investigation;

Tai: the number of surviving insects in the treatment group at the time of investigation;

As a result, as shown in [Table 21] to [Table 22], compounds of the present invention 3, 15, 19, 20, 48, 50, 72, 81, 85, 99, 130, 421, 444, 445 were contained, respectively , 464 and 467 and the compositions of the present invention of triflumezopyrim showed excellent control efficacy.

Here, the respective control values of triflumezopyrim or the compounds of the present invention alone, observed in experiments similar to those described above, are shown below. For triflumezopyrim, 4 (concentration 0.1 ppm) and 30 (concentration 1 ppm); for inventive compounds 15, 28 (concentration 1 ppm); for inventive compounds 20, 12 (concentration 0.01 ppm); for inventive compounds 72, 32 (concentration 10ppm); for compounds of the invention 444, 32 (concentration 1 ppm); for compounds of the invention 445, 30 (concentration 0.1 ppm) and 37 (concentration 1 ppm).

[Table 21]

[Table 22]

Industrial Applicability

The present invention can control harmful organisms.

Claims (6)

1. A composition for controlling harmful bio-organisms, comprising:

a compound represented by formula (1):

wherein,

A¹represents-NMe-, or an oxygen atom,

A²is represented by N-,N (→ O) -or CH-,

q represents-N-,

R¹represents a C1-C6 alkyl group,

R²and R⁴Each represents a hydrogen atom, and each represents a hydrogen atom,

R³represents a C1-C3 alkyl group optionally having one or more halogen atoms, or a hydrogen atom,

R⁵represents C1-C3 alkyl, -OR optionally having one OR more halogen atoms¹⁰or-S (O)_mR¹⁰，

R⁶represents-NR¹⁰R¹¹Or a hydrogen atom,

R¹⁰and R¹¹Identical or different from each other and each represents a C1-C3 alkyl group optionally having one or more halogen atoms,

m independently of one another represents 0, 1 or 2, and

n represents 2, and

2, 4-dioxo-1- (5-pyrimidinylmethyl) -3- [3- (trifluoromethyl) phenyl]-2H-pyrido [1,2-a]PyrimidinesThe content of the internal salt is as follows,

wherein the compound represented by the formula (1) is reacted with 2, 4-dioxo-1- (5-pyrimidinylmethyl) -3- [3- (trifluoromethyl) phenyl group]-2H-pyrido [1,2-a]PyrimidinesThe ratio of the inner salt is in the range of 100:1 to 1:100 by weight.

2. The composition for controlling harmful bio-organisms according to claim 1, wherein A¹represents-NMe-.

3. The composition for controlling harmful bio-organisms according to claim 1, wherein A¹Represents an oxygen atom.

4. The composition for controlling harmful bio-organisms according to any one of claims 1 to 3, wherein the compound represented by formula (1) is reacted with 2, 4-dioxo-1- (5-pyrimidinylmethyl) -3- [3- (trifluoromethyl) phenyl group]-2H-pyrido [1,2-a]PyrimidinesThe ratio of the inner salt is in the range of 10:1 to 1:10 by weight.

5. A method for controlling pests, which comprises applying an effective amount of the composition for controlling pests according to any one of claims 1 to 4 to the pests or a habitat where the pests live.

6. A method for controlling harmful bio-organisms, which comprises applying an effective amount of the composition for controlling harmful bio-organisms according to any one of claims 1 to 4 to a plant, a plant seed, a bulb, or soil for cultivating the plant.