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 composition and application thereof

Technical field

The present invention relates to the composition for preventing and treating harmful organism and the methods for preventing and treating harmful organism.

Background technique

So far, it is known that many compounds as the composition for preventing and treating harmful organism active constituent (referring to special Sharp document 1 to 3 and non-patent literature 1).

Quote inventory

Patent document

2013/018928 pamphlet of patent document 1:WO

2012/092115 pamphlet of patent document 2:WO

2014/104407 pamphlet of patent document 3:WO

Non-patent literature

Non-patent literature 1: pesticide manual (THE Pesticide Manual)-the 16 edition is published, ISBN by BCPC 9781901396867

Summary of the invention

(the technical problem to be solved in the present invention)

It is an object of the present invention to provide harmful organism is used to prevent and treat harmful organism with excellent preventing efficiency Composition.

(means solved the problems, such as)

The present inventor's further investigation is to find a kind of pair of harmful organism with excellent preventing efficiency for preventing and treating The composition of harmful organism.As a result, they have found that a kind of such composition has excellent prevention and treatment to harmful organism Effect, the composition include the compound indicated by formula (1) mentioned below, and

2,4- dioxo -1- (5- Pyrimidylmethyl) -3- [3- (trifluoromethyl) phenyl] -2H- pyrido [1,2-a] pyrimidineInner salt (hereinafter, referred to " Triflumezopyrim ").

The present invention provides such as following embodiments.

[1] a kind of for preventing and treating the composition of harmful organism, the composition for preventing and treating harmful organism includes

The compound indicated by formula (1):

Wherein,

A¹Expression-NR⁷, oxygen atom or sulphur atom,

A²Expression=N- ,=N (→ O)-or=CR⁸,

Q expression=N- or=N (→ O)-,

R¹Indicate the C1-C6 alkyl optionally with one or more atoms selected from X group or group,

R²、R³And R⁴It is same or different to each other, and respectively indicates that optionally there are one or more atoms for being selected from X group Or C1-C6 the alkyl ,-OR of group¹⁰、-S(O)_mR¹⁰、-S(O)₂NR¹⁰R¹¹、-NR¹⁰R¹¹、-NR¹⁰CO₂R¹¹、-NR¹⁰C(O)R¹¹、- CO₂R¹⁰、-C(O)R¹⁰、-C(O)NR¹⁰R¹¹、-SF₅, cyano, nitro, halogen atom or hydrogen atom,

R⁵And R⁶It is same or different to each other, and respectively indicates that optionally there are one or more atoms or base for being selected from X group C1-C6 the alkyl ,-OR of group¹⁰、-S(O)_mR¹⁰、-S(O)₂NR¹⁰R¹¹、-NR¹⁰R¹¹、-NR¹⁰CO₂R¹¹、-NR¹⁰C(O)R¹¹、- CO₂R¹⁰、-C(O)R¹⁰、-C(O)NR¹⁰R¹¹、-OC(O)R¹⁰、-SF₅, cyano, nitro, (condition is: R for halogen atom or hydrogen atom⁵ And R⁶Hydrogen atom is not indicated simultaneously),

R⁷Indicate C1-C6 the alkyl ,-CO optionally with one or more atoms selected from W group or group₂R¹⁰、-C(O) R¹⁰、-CH₂CO₂R¹⁰, C3-C6 naphthenic base or hydrogen atom,

R⁸Indicate C1-C6 the alkyl ,-OR optionally with one or more halogen atoms¹⁰、-S(O)_mR¹⁰、-NR¹⁰R¹¹、- CO₂R¹⁰、-C(O)R¹⁰, cyano, nitro, halogen atom or hydrogen atom,

R¹⁰And R¹¹Be same or different to each other, and respectively indicate optionally to have one or more atoms selected from X group or (condition is the C1-C6 alkyl or hydrogen atom of group: at-S (O)_mR¹⁰In, when m is 1 or 2, R¹⁰Do not indicate hydrogen atom),

M indicates 0,1 or 2 independently of one another, and

N indicates 0,1 or 2,

X group: by optionally with one or more halogen atoms C1-C6 alkoxy, optionally there is one or more The group of the C3-C6 naphthenic base of halogen atom or one or more C1-C3 alkyl, cyano, hydroxyl and halogen atom composition,

W group: C1-C6 alkoxy optionally with one or more halogen atoms optionally has one or more halogen C3-C6 naphthenic base, hydroxyl, halogen atom or the cyano of plain atom], and

2,4- dioxo -1- (5- Pyrimidylmethyl) -3- [3- (trifluoromethyl) phenyl] -2H- pyrido [1,2-a] pyrimidineInner salt (triflumezopyrim) (hereinafter, referred to " composition of the invention ").

[2] described in [1] for preventing and treating the composition of harmful organism, wherein A¹Expression-NMe-, oxygen atom or sulphur are former Son, A²Expression=N- ,=N (→ O)-or=CH-, R¹Indicate the C1-C6 alkyl optionally with one or more halogen atoms, R²And R⁴Indicate hydrogen atom, R³Indicate the C1-C3 alkyl or hydrogen atom optionally with one or more halogen atoms, R⁵It indicates Optionally there is C1-C3 the alkyl ,-OR of one or more halogen atoms¹⁰Or-S (O)_mR¹⁰, R⁶Expression-NR¹⁰R¹¹Or hydrogen atom, And R¹⁰And R¹¹The C1-C3 alkyl optionally with one or more halogen atoms is indicated independently of one another.

[3] it is used to prevent and treat the composition of harmful organism described in [1] or [2], wherein A¹Expression-NMe-.

[4] it is used to prevent and treat the composition of harmful organism described in [1] or [2], wherein A¹Indicate oxygen atom.

[5] for preventing and treating the composition of harmful organism described in any one of [1] to [4], wherein described by formula (1) table The compound and 2,4- dioxo -1- (5- Pyrimidylmethyl) -3- [3- (trifluoromethyl) phenyl] -2H- pyrido [1,2-a] shown PyrimidineThe ratio of inner salt is by weight in the range of 100: 1 to 1: 100.

[6] for preventing and treating the composition of harmful organism described in any one of [1] to [4], wherein described by formula (1) table The compound and 2,4- dioxo -1- (5- Pyrimidylmethyl) -3- [3- (trifluoromethyl) phenyl] -2H- pyrido [1,2-a] shown PyrimidineThe ratio of inner salt is by weight in the range of 10: 1 to 1: 10.

[7] a kind of method for preventing and treating harmful organism, the method includes what is lived to harmful organism or harmful organism A effective amount of composition for being used to prevent and treat harmful organism described in any one of [1] to [6] of habitat application.

[8] a kind of method for preventing and treating harmful organism, the method includes to plant, vegetable seeds, bulb or being used for Cultivate a effective amount of combination for being used to prevent and treat harmful organism described in any one of [1] to [6] of soil application of the plant Object.

[9] seed or bulb of a kind of plant, the seed or bulb of the plant are attached to a effective amount of in [1] to [6] For preventing and treating the composition of harmful organism described in any one.

[The effect of invention]

The present invention can prevent and treat harmful organism.

Specific embodiment

The composition for preventing and treating harmful organism of the invention include it is above-mentioned indicated by formula (1) compound (under Wen Zhong, referred to as " the compounds of this invention ") and triflumezopyrim.

Group as described herein is explained as follows.

As used herein, statement " Ca-Cb alkyl " indicates the linear chain or branched chain alkyl with " a " extremely " b " a carbon atom.

Stating " Ca-Cb halogenated alkyl " indicates the linear chain or branched chain alkyl with " a " extremely " b " a carbon atom, wherein with carbon One or more hydrogen atoms of atom connection are substituted by one or more halogen atoms.When there is more than two halogen atoms, The halogen atom each other can be identical or different.

Stating " Ca-Cb alkoxy " indicates the linear or branched alkyl group-O- group with " a " extremely " b " a carbon atom.

Stating " Ca-Cb naphthenic base " indicates the saturated cyclic hydrocarbon group with " a " extremely " b " a carbon atom.

As used herein, it states " optionally there are one or more atoms or group for being selected from X group " and indicates to work as and exist When more than two atoms or group, atom or group selected from X group each other can be identical or different.

As used herein, it states " optionally there are one or more atoms or group for being selected from W group " and indicates to work as and exist When two or more is selected from the atom or group of W group, the atom or group each other can be identical or different.

As used herein, statement " optionally having one or more halogen atoms ", which indicates to work as, has more than two halogens Atomic time, the halogen atom each other can be identical or different.

In the compounds of this invention, as used herein, term " halogen atom " indicates fluorine atom, chlorine atom, bromine atom And iodine atom.

In the compounds of this invention, statement " optionally has the C1-C6 of one or more atoms selected from X group or group Alkyl " indicates the linear chain or branched chain saturated hydrocarbyl with 1 to 6 carbon atom, wherein the hydrogen atom connecting with carbon atom can appoint Selection of land is by atom or group substitution selected from X group.When there is more than two atoms or group, atom or group selected from X group It each other can be identical or different.

The example of " the C1-C6 alkyl optionally with one or more atoms selected from X group or group " includes by following The C1-C6 alkyl optionally with one or more atoms selected from X group or group of items composition: methyl, ethyl, propyl, Isopropyl, butyl, isobutyl group, sec-butyl, tert-butyl, amyl, neopentyl, hexyl, methoxy, ethoxyl methyl, the third oxygen Ylmethyl, i-propoxymethyl, butoxymethyl, sec-butoxymethyl, t-butoxymethyl, 2- methoxy ethyl, 2- ethoxy Base ethyl, 2- Among, 2- isopropoxyethyl, 2- butoxyethyl group, 2- sec-butoxy ethyl, 2- tert-butoxy second Base, trifluoromethyl, trichloromethyl, 2- fluoro ethyl, 2,2- bis-fluoro ethyls, 2,2,2- trifluoroethyl and pentafluoroethyl group, 2- hydroxyl second Base, Cvclopropvlmethvl, 1- methylcyclopropylmethyl, 2,2- difluorocyclopropyl methyl, trimethoxy methyl, triethoxy methyl Deng being selected according to specified carbon atom number.

In the compounds of this invention, statement " optionally having the C1-C6 alkyl of one or more halogen atoms " indicates tool There is the linear chain or branched chain saturated hydrocarbyl of 1 to 6 carbon atom, wherein the hydrogen atom connecting with carbon atom can be optionally by halogen original Son substitution, and when there is more than two halogen atoms, the halogen atom each other can be identical or different.

The example of " the C1-C6 alkyl optionally with one or more halogen atoms " includes optional selected from the following terms Ground has a C1-C6 alkyl of one or more halogen atoms: methyl, ethyl, propyl, isopropyl, butyl, isobutyl group, sec-butyl, Tert-butyl, amyl, neopentyl, hexyl, trifluoromethyl, trichloromethyl, 2- fluoro ethyl, 2,2- bis-fluoro ethyls, 2,2,2- trifluoro second Base and pentafluoroethyl group or hepta-fluoroiso-propyl etc. are selected according to specified carbon atom number.

In the compounds of this invention, " the C1-C6 alkyl optionally with one or more atoms selected from W group or group " Example include the C2-C6 alkyl optionally with one or more atoms selected from W group or group being made of the following terms: Methyl, ethyl, propyl, isopropyl, butyl, isobutyl group, sec-butyl, tert-butyl, amyl, neopentyl, hexyl, trifluoromethyl, three Chloromethyl, 2- fluoro ethyl, 2,2- bis-fluoro ethyls, 2,2,2- trifluoroethyl, pentafluoroethyl group, methoxy, ethoxyl methyl, third Oxygroup methyl, i-propoxymethyl, butoxymethyl, sec-butoxymethyl, isobutoxymethyl, t-butoxymethyl, methoxy Base ethyl, ethoxyethyl group, Among, isopropoxyethyl, butoxyethyl group, sec-butoxy ethyl, isobutoxy second Base, t-butoxy ethyl etc..When there is more than two atoms or group for being selected from W group, the atom or group selected from W group It each other can be identical or different.

In the compounds of this invention, the example packet of " the C1-C6 alkoxy optionally with one or more halogen atoms " Include methoxyl group, trifluoromethoxy, ethyoxyl, 2,2,2- trifluoro ethoxy, propoxyl group, isopropoxy, butoxy, isobutoxy, Sec-butoxy, tert-butoxy, amoxy and hexyloxy.

In the compounds of this invention, the example packet of " the C3-C6 naphthenic base optionally with one or more halogen atoms " Include cyclopropyl, 2,2- difluorocyclopropyl, 2,2- dichloro cyclopropyl, 2,2- dibromo cyclopropyl, cyclobutyl, cyclopenta and cyclohexyl.

In the compounds of this invention, " optionally there is one or more halogen atoms or one or more C1-C3 alkyl C3-C6 naphthenic base " example include cyclopropyl, 1- methylcyclopropyl groups, 2- methylcyclopropyl groups, 1- fluorine cyclopropyl, 2,2- difluoro Cyclopropyl, 2,2- dichloro cyclopropyl, 2,2- dibromo cyclopropyl, cyclobutyl, cyclopenta and cyclohexyl.

In the compounds of this invention, statement " C1-C3 halogenated alkyl " indicates the linear chain or branched chain with 1 to 3 carbon atom Alkyl, wherein the one or more hydrogen atoms connecting with carbon atom are substituted by one or more halogen atoms, and when there are two When a above halogen atom, the halogen atom each other can be identical or different.

The example of " C1-C3 halogenated alkyl " includes methyl fluoride, chloromethyl, bromomethyl, iodomethyl, difluoromethyl, dichloromethane Base, trifluoromethyl, chlorodifluoramethyl-, bromine difluoro methyl, trichloromethyl, 2- fluoro ethyl, 2- chloroethyl, 2- bromoethyl, 2,2- bis- Fluoro ethyl, 2,2,2- trifluoroethyl, pentafluoroethyl group, heptafluoropropyl, hepta-fluoroiso-propyl etc..

In the compounds of this invention, the example of " C1-C3 alkyl " includes methyl, ethyl, propyl and isopropyl.

In the compounds of this invention, the example of " C1-C3 perfluoroalkyl " includes trifluoromethyl, pentafluoroethyl group, heptafluoropropyl And hepta-fluoroiso-propyl.

In a certain embodiment, the example of the compounds of this invention includes as following [table 1] is listed into [table 20] The compound indicated by formula (1).

[table 1]

Number

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

21

Et

H

H

H

I

H

NMe

CH

0

N

22*

Et

H

H

H

CF3

H

S

N(→O)

2

N

23

Et

H

H

H

SF5

H

NMe

CH

0

N

24

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]

Number

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]

Number

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]

Number

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]

Number

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]

Number

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

CH2CN

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

CH2CN

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]

Number

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

CN

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]

Number

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]

Number

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, such as symbol in the compounds of this invention listed into [table 20] at above-mentioned [table 1] Number " * " indicates N- oxide.Its specific example includes following.

At above-mentioned [table 1] into [table 20], Me indicates that methyl, Et indicate that ethyl, Pr indicate that propyl, Bu indicate fourth Base, tBu indicate that tert-butyl, iPr indicate isopropyl, and CycPr indicates cyclopropyl, and CycBu indicates cyclobutyl.

These compounds can be according to described in 2014/104407 pamphlet of 2013/018928 pamphlet of WO or WO Method preparation.About some compounds among them, preparation method is described below.

Preparation example 1 (1)

By iodo- 3- methyl -3H- imidazo [4,5-b] the pyridine 1.1g of 2- (3- ethylmercapto group-pyridine -2- base) -6-, cupric iodide (1) mixture of 160mg, 9 hydrate 2.7g of sodium sulphate and n,N-Dimethylformamide (hereinafter, referred to DMF) 10mL are 110 DEG C stirring 5 hours.Water is added into reaction mixture, and mixture is extracted with ethyl acetate.Organic layer is dry with sodium sulphate And it is concentrated under reduced pressure.Make residue by silica gel column chromatography, obtain the compound indicated by formula mentioned below:

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

¹H-NMR(DMSO-D₆) 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)

The mixture of compound (1-1) 710mg and DMF 12mL is cooled to -60 DEG C, and trifluoro iodine first is added thereto Alkane 10g.At -40 DEG C, four (dimethylamino) ethylene 1.2mL are added dropwise into mixture.Mixture is warmed to -10 DEG C simultaneously It is stirred 5 hours at -10 DEG C.Water is added into reaction mixture, and mixture is extracted with ethyl acetate.Organic layer sodium sulphate It dries and is concentrated under reduced pressure.Make residue by silica gel column chromatography, obtains 2- (3- ethylmercapto group-pyridine -2- base) -3- methyl - 6- trifluoromethylthio -3H- imidazo [4,5-b] pyridine (hereinafter, referred to " the compounds of this invention 13 ") 530mg.

¹H-NMR(CDCl₃) 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

By 13 200mg of the compounds of this invention, metachloroperbenzoic acid (65% or more purity) 230mg and chloroform 10mL it is mixed Object is closed to stir under ice-cooling 5 hours.Saturated sodium bicarbonate aqueous solution is added into reaction mixture and by mixture chloroform Extraction.Organic layer sodium sulphate is dry and is concentrated under reduced pressure.Make residue by silica gel column chromatography, obtains 2- (3- ethylmercapto group- Pyridine -2- base) -3- methyl -6- trifluoromethylthio -3H- imidazo [4,5-b] pyridine is (hereinafter, referred to " the compounds of this invention 14 ") 89mg and 2- (3- ethylsulfonyl-pyridine -2- base) -3- methyl -6- trifluoromethylthio -3H- imidazo [4,5-b] pyridine (hereinafter, referred to " the compounds of this invention 15 ") 130mg.

The compounds of this invention 14

¹H-NMR(CDCl₃) 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)。

The compounds of this invention 15

¹H-NMR(CDCl₃) 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)

Under ice-cooling, to the chloro- 2- cyanopyridine 1.39g of 3-, ethyl mercaptan 0.9mL and DMF 10mL mixture in be added Sodium hydride (60%, oily material) 0.52g, and mixture is stirred at room temperature 1 hour.Water is added into reaction mixture, and Mixture is extracted with ethyl acetate.Organic layer is washed with saturated sodium bicarbonate aqueous solution and saturated brine, and mixture is used Anhydrous sodium sulfate is dry and is concentrated under reduced pressure.Make resulting residue by silica gel column chromatography, obtains 2- cyano -3- ethylmercapto group Pyridine 1.52g.

¹H-NMR(CDCl₃) δ: 8.49 (1H, dd), 7.75 (1H, dd), 7.43 (1H, dd), 3.06 (2H, q), 1.38 (3H, t)。

Preparation example 3 (2)

To addition 2- cyano -3- ethylmercapto group pyridine 1.4g in the mixture of concentrated sulfuric acid 15mL and water 5mL, and mixture is existed 130 DEG C are stirred 2 hours.Allow reaction mixture to be cooled to room temperature, and potassium hydroxide aqueous solution is added thereto, and by mixture It is extracted with ethyl acetate.Concentrated hydrochloric acid is added into resulting water layer, and mixture is extracted with chloroform and is done with anhydrous sodium sulfate It is dry, it is then concentrated under reduced pressure, obtains 3- ethylmercapto group pyridine carboxylic acid 1.15g.

¹H-NMR(CDCl₃) 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 (is passed through into the method system described in 2009/131237 pamphlet of WO It is standby) 1.0g, 3- ethylmercapto group pyridine carboxylic acid 0.87g, 1- ethyl -3- (3- diformazan dimethylaminopropyl) carbodiimide hydrochloride The mixture of 1.10g and chloroform 10mL are stirred at room temperature 30 minutes.It is added water into reaction mixture, and by mixture acetic acid Ethyl ester extraction.Organic layer is washed with saturated sodium bicarbonate aqueous solution and saturated brine, and dry with anhydrous magnesium sulfate, and is being depressurized Lower concentration.Make resulting residue by silica gel column chromatography, obtains 3- ethylmercapto group-N- [2- hydroxyl -5- (trifluoromethylthio) benzene Base] picolinamide (hereinafter, referred to " compound 3-3 ") 1.32g.

Compound 3-3

¹H-NMR(CDCl₃) 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)

By compound 3-3 1.23g, two -2- methoxy ethyl azodiformate 1.28g, triphenylphosphine 1.39g and four The mixture of hydrogen furans 30mL is stirred at room temperature 1 hour and stirs 1 hour at 50 DEG C.Reaction mixture is allowed to be cooled to room temperature, Then it is concentrated under reduced pressure, and water is added thereto, and mixture is extracted with ethyl acetate.Organic layer saturated sodium bicarbonate Aqueous solution and saturated brine washing, and with anhydrous magnesium sulfate drying and be concentrated under reduced pressure.Make resulting residue by silica gel Column chromatography obtains 2- (3- ethylmercapto group pyridine -2- base) -5- (trifluoromethylthio) benzoAzoles is (hereinafter, referred to " present inventionization Close object 441 ") 1.21g.

¹H-NMR(CDCl₃) 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

Under ice-cooling, m-chloro is added into the mixture of the compounds of this invention 441 (1.06g) and chloroform 30mL and crosses benzene first Acid (65% or more purity) 1.47g, and mixture is stirred at room temperature 6 hours.10% sulfurous acid is added into reaction mixture Sodium water solution, and mixture is extracted with chloroform.Organic layer is washed with saturated sodium bicarbonate aqueous solution, and dry with anhydrous magnesium sulfate It is dry, then it is concentrated under reduced pressure.Make resulting residue by silica gel column chromatography, obtains 2- (3- ethylsulfonyl pyridine -2- Base) -5- (trifluoromethylthio) benzoAzoles (hereinafter, referred to " the compounds of this invention 443 ") 0.87g and 2- (3- ethyl sulphonyl Yl pyridines -2- base) -5- (trifluoromethyl sulphinyl base) benzoAzoles (hereinafter, referred to " the compounds of this invention 444 ") 0.17g.

The compounds of this invention 443

¹H-NMR(CDCl₃) 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)。

The compounds of this invention 444

¹H-NMR(CDCl₃) 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

Under ice-cooling, metachloroperbenzoic acid is added into the mixture of the compounds of this invention 443 0.35g and chloroform 8mL (65% or more purity) 0.43g, and mixture is stirred 6 hours at 40 DEG C.Allow reaction mixture be cooled to room temperature, and to its 10% sodium sulfite aqueous solution of middle addition, and mixture is extracted with chloroform.Organic layer is washed with saturated sodium bicarbonate aqueous solution, And it is dry with anhydrous magnesium sulfate, then it is concentrated under reduced pressure.Acetonitrile 4mL, 2 hydrate of sodium tungstate are added into resulting residue 30mg and hydrogenperoxide steam generator (30%) 4mL, and mixture is stirred 6 hours at 80 DEG C.Reaction mixture is allowed to be cooled to room Temperature, and water is added thereto, and the solid of precipitating is collected by filtration, and 10% sodium sulfite aqueous solution is added into filtrate, And mixture is extracted with ethyl acetate.Organic layer is washed with water and saturated brine, with anhydrous magnesium sulfate drying and under reduced pressure Concentration.Make resulting residue by silica gel column chromatography, obtains 2- (3- ethylsulfonyl pyridine -2- base) -5- (trifluoromethyl sulphur Acyl group) benzoAzoles (hereinafter, referred to " the compounds of this invention 445 ") 0.35g.

The compounds of this invention 445

¹H-NMR(CDCl₃) 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 the form of mesoionic inner salt, and passes through following six structure Formula indicates.

Triflumezopyrim can be prepared according to the method described in 2012/092115 pamphlet of WO, and In the document, 2- hydroxyl -4- oxo -1- (5- Pyrimidylmethyl) -3- [3- (trifluoromethyl) phenyl] -4H- pyrrole is described it as Pyridine simultaneously [1,2-a] pyridineMolecule inner salt (intermolecular salt).

In a certain embodiment, the example of the present composition includes following.

It is a kind of for preventing and treating the composition of harmful organism, it includes the compound indicated by formula (1), wherein A¹Indicate- NMe-, oxygen atom or sulphur atom, A²Expression=N- ,=N (→ O)-or=CH-, R¹Indicate that optionally there are one or more halogens The C1-C6 alkyl of atom, R²And R⁴Respectively indicate hydrogen atom, R³Indicate the C1-C3 optionally with one or more halogen atoms Alkyl or hydrogen atom, R⁵Indicate C1-C3 the alkyl ,-OR optionally with one or more halogen atoms¹⁰Or-S (O)_mR¹⁰, R⁶ Expression-NR¹⁰R¹¹Or hydrogen atom, and R¹⁰And R¹¹The C1- optionally with one or more halogen atoms is indicated independently of one another C3 alkyl；And triflumezopyrim.

It is a kind of for preventing and treating the composition of harmful organism, it includes the compound indicated by formula (1), wherein A¹Indicate- NMe- or oxygen atom, A2 expression=N- ,=N (→ O)-or=CH-, R¹Indicate that optionally there are one or more halogen atoms C1-C6 alkyl, R²And R⁴Respectively indicate hydrogen atom, R³Indicate optionally to have the C1-C3 alkyl of one or more halogen atoms or Hydrogen atom, R⁵Indicate C1-C3 the alkyl ,-OR optionally with one or more halogen atoms¹⁰Or-S (O)_mR¹⁰, R⁶Indicate- NR¹⁰R¹¹Or hydrogen atom, and R¹⁰And R¹¹The C1-C3 alkane optionally with one or more halogen atoms is indicated independently of one another Base；And triflumezopyrim.

It is a kind of for preventing and treating the composition of harmful organism, it includes the compound indicated by formula (1), wherein A¹Indicate- NMe- or oxygen atom, A²Expression=N- ,=N (→ O)-or=CH-, R¹Indicate C1-C6 alkyl, R²、R⁴And R⁶Respectively indicate that hydrogen is former Son, R³Indicate the C1-C3 alkyl or halogen atom optionally with one or more halogen atoms, R⁵Indicate optionally there is one C1-C3 the alkyl ,-OR of a or multiple halogen atoms¹⁰Or-S (O)_mR¹⁰, and R¹⁰Indicate that optionally there are one or more halogen The C1-C3 alkyl of plain atom；And triflumezopyrim.

It is a kind of for preventing and treating the composition of harmful organism, it includes the compound indicated by formula (1), wherein A¹Indicate- NMe-, A²Expression=N- or=N (→ O)-, R¹Indicate C1-C6 alkyl, R²、R⁴And R⁶Respectively indicate hydrogen atom, R³It indicates optionally C1-C3 alkyl or hydrogen atom with one or more halogen atoms, R⁵Indicate that optionally there are one or more halogen atoms C1-C3 alkyl or-S (O)_mR¹⁰, and R¹⁰Indicate the C1-C3 alkyl optionally with one or more halogen atoms；With triflumezopyrim。

It is a kind of for preventing and treating the composition of harmful organism, it includes the compound indicated by formula (1), wherein A¹Indicate that oxygen is former Son, A²Expression=N- ,=N (→ O)-or=CH-, R¹Indicate C1-C6 alkyl, R²、R⁴And R⁶Respectively indicate hydrogen atom, R³It indicates to appoint Selection of land has the C1-C3 alkyl or hydrogen atom of one or more halogen atoms, R⁵Indicate that optionally there are one or more halogens C1-C3 the alkyl ,-OR of atom¹⁰Or S (O)_mR¹⁰, and R¹⁰Indicate the C1-C3 optionally with one or more halogen atoms Alkyl；And triflumezopyrim.

It is a kind of for preventing and treating the composition of harmful organism, it includes the compound indicated by formula (1), wherein A¹Indicate that oxygen is former Son, A²Expression=N- or=N (→ O)-, R¹Indicate the C1-C6 alkyl optionally with one or more halogen atoms, R²、R³、R⁴ And R⁶Respectively indicate hydrogen atom, R⁵Indicate the C1-C3 alkyl or-S (O) optionally with one or more halogen atoms_mR¹⁰, and And R¹⁰Indicate the C1-C3 alkyl optionally with one or more halogen atoms；And triflumezopyrim.

It is a kind of for preventing and treating the composition of harmful organism, it includes the compound indicated by formula (1), wherein A¹Indicate that oxygen is former Son, A²Expression=N-, R¹Indicate C1-C6 alkyl, R²、R³、R⁴And R⁶Respectively indicate hydrogen atom, R⁵Indicate optionally have one or The C1-C3 alkyl of multiple halogen atoms or-S (O)_mR¹⁰, and R¹⁰Indicate the C1- optionally with one or more halogen atoms C3 alkyl；And triflumezopyrim.

It is a kind of for preventing and treating the composition of harmful organism, it includes the compound indicated by formula (1), wherein A¹Indicate that oxygen is former Son, A²Expression=CH-, R¹Indicate the C1-C6 alkyl optionally with one or more halogen atoms, R²、R³、R⁴And R⁶Respective table Show hydrogen atom, R⁵Indicate the C1-C3 alkyl or-S (O) optionally with one or more halogen atoms_mR¹⁰, and R¹⁰It indicates to appoint Selection of land has the C1-C3 alkyl of one or more halogen atoms；And triflumezopyrim.

It is a kind of for preventing and treating the composition of harmful organism, it includes the compound indicated by formula (1), wherein A¹Indicate that oxygen is former Son, A²Expression=CH-, R¹Indicate C1-C6 alkyl, R²、R³、R⁴And R⁶Respectively indicate hydrogen atom, R⁵Indicate that optionally there is one Or the C1-C3 alkyl or-S (O) of multiple halogen atoms_mR¹⁰, and R¹⁰Indicate that optionally there are one or more halogen atoms C1-C3 alkyl；And triflumezopyrim.

It is a kind of for preventing and treating the composition of harmful organism, it includes the compound indicated by formula (1), wherein R¹Indicate optional C1-C6 alkyl (Y group: by optionally have one or more halogens of the ground with one or more atoms selected from Y group or group The group of C3-C6 naphthenic base and the halogen atom composition of atom), R²And R⁴Respectively indicate hydrogen atom, R³Indicate optionally there is one C1-C3 alkyl, the-C (OR of a or multiple halogen atoms¹⁰)₃, halogen atom or hydrogen atom, R⁵Indicate optionally have one or C1-C3 the alkyl ,-OR of multiple halogen atoms¹⁰、-S(O)_mR¹⁰、-CO₂R¹⁰、-SF₅Or halogen atom, R⁶Expression-OR¹⁰、- NR¹⁰R¹¹、-CO₂R¹⁰、-C(O)NR¹⁰R¹¹、-OC(O)R¹⁰, cyano, halogen atom or hydrogen atom, R⁷Indicate that optionally there is one Or C1-C6 the alkyl ,-CH of multiple halogen atoms₂CO₂R¹⁰, C3-C6 naphthenic base or hydrogen atom, R⁸Indicate optionally have one or C1-C3 the alkyl ,-OR of multiple halogen atoms¹⁰、-S(O)_mR¹⁰, cyano, halogen atom or hydrogen atom, R¹⁰And R¹¹Independently of one another (condition is the C1-C3 alkyl or hydrogen atom that expression optionally has one or more halogen atoms: at-S (O)_mR¹⁰In, when m is When 1 or 2, R¹⁰Do not indicate hydrogen atom)；And triflumezopyrim.

It is a kind of for preventing and treating the composition of harmful organism, it includes the compound indicated by formula (1), wherein R¹Indicate optional Ground has the C1-C3 alkyl of one or more halogen atoms, R²And R⁴Respectively indicate hydrogen atom, R³Indicate that optionally there is one Or C1-C3 alkyl, the-C (OR of multiple halogen atoms¹⁰)₃, halogen atom or hydrogen atom, R⁵Indicate that optionally there is one or more C1-C3 the alkyl ,-OR of a halogen atom¹⁰、-S(O)_mR¹⁰Or halogen atom, R⁶Indicate cyano ,-NR¹⁰R¹¹, halogen atom or hydrogen Atom, R⁷Indicate the C1-C6 alkyl optionally with one or more halogen atoms, R⁸Expression-S (O)_mR¹⁰, cyano, halogen it is former Son or hydrogen atom, and R¹⁰And R¹¹Cyano, halogen atom or hydrogen atom, and R are respectively indicated independently of one another¹⁰And R¹¹Respectively The C1-C3 alkyl optionally with one or more halogen atoms is indicated independently of one another；And triflumezopyrim.

It is a kind of for preventing and treating the composition of harmful organism, it includes the compound indicated by formula (1), wherein R¹Indicate second Base, R²And R⁴Respectively indicate hydrogen atom, R³Indicate C1-C3 the alkyl ,-C optionally with one or more halogen atoms (OR¹⁰)₃, halogen atom or hydrogen atom, R⁵Indicate C1-C3 halogenated alkyl ,-OR²⁰、-S(O)_mR²⁰Or halogen atom (R²⁰It indicates C1-C3 halogenated alkyl), R⁶Indicate cyano ,-NR¹⁰R¹¹, halogen atom or hydrogen atom, R⁷Indicate that optionally there is one or more The C1-C6 alkyl of halogen atom, R⁸Expression-S (O)_mR¹⁰, cyano, halogen atom or hydrogen atom, and R¹⁰And R¹¹Independently of one another Indicate the C1-C3 alkyl optionally with one or more halogen atoms；And triflumezopyrim.

It is a kind of for preventing and treating the composition of harmful organism, it includes the compound indicated by formula (1), wherein A¹Indicate- NR⁷-；And triflumezopyrim.

It is a kind of for preventing and treating the composition of harmful organism, it includes the compound indicated by formula (1), wherein A¹Indicate that oxygen is former Son；And triflumezopyrim.

It is a kind of for preventing and treating the composition of harmful organism, it includes the compound indicated by formula (1), wherein A¹Indicate- NR⁷, R¹Indicate C1-C3 alkyl, R²And R⁴Respectively indicate hydrogen atom, R³Indicate that optionally there are one or more halogen atoms C1-C3 alkyl R³Indicate C1-C3 alkyl, the-C (OR optionally with one or more halogen atoms¹⁰)₃, halogen atom or hydrogen Atom, R⁵Indicate C1-C3 halogenated alkyl ,-OR²⁰、-S(O)_mR²⁰Or halogen atom, R⁶Indicate cyano ,-NR¹⁰R¹¹, halogen atom or Hydrogen atom, R⁷Indicate the C1-C6 alkyl optionally with one or more halogen atoms, R⁸Expression-S (O)_mR¹⁰, cyano, halogen Atom or hydrogen atom, and R¹⁰And R¹¹The C1-C3 alkane optionally with one or more halogen atoms is indicated independently of one another Base, and R²⁰Indicate C1-C3 halogenated alkyl；And triflumezopyrim.

It is a kind of for preventing and treating the composition of harmful organism, it includes the compound indicated by formula (1), wherein A¹Indicate that oxygen is former Son, R¹Indicate ethyl, R²、R⁴And R⁶Respectively indicate hydrogen atom, R³Indicate the C1-C3 optionally with one or more halogen atoms Alkyl ,-C (OR¹⁰)₃, halogen atom or hydrogen atom, R⁵Indicate C1-C3 halogenated alkyl ,-OR²⁰、-S(O)_mR²⁰Or halogen atom, R⁸ Expression-S (O)_mR¹⁰, cyano, halogen atom or hydrogen atom, R¹⁰Indicate the C1-C3 optionally with one or more halogen atoms Alkyl, and R²⁰Indicate C1-C3 halogenated alkyl；And triflumezopyrim.

It is a kind of for preventing and treating the composition of harmful organism, it includes the compound indicated by formula (1), wherein A¹Indicate that oxygen is former Son, R¹Indicate ethyl, R²、R⁴And R⁶Respectively indicate hydrogen atom, R³Indicate halogen atom or hydrogen atom, R⁵Indicate C1-C3 perfluor alkane Base ,-OR³⁰Or-S (O) mR³⁰, R³⁰Indicate C1-C3 perfluoroalkyl, and R⁸Indicate halogen atom or hydrogen atom；With triflumezopyrim。

Composition of the invention can be only the compounds of this invention and the mixture of triflumezopyrim, however, usually It is prepared by mixing the compounds of this invention and triflumezopyrim with inert carrier, and if desired, addition surface Activating agent and other adjuvants for preparation, be configured to oil solution, missible oil (emulsifiable concentrate), can Flowable (flowables), wettable powder, granular wettable powder, powderous preparations (dust formulations), particle Agent etc..

Moreover, the composition for preventing and treating harmful organism prepared above can be with its own or by adding other inertia Ingredient uses.

In the present compositions, the total amount of the compounds of this invention and triflumezopyrim are usually in 0.1 weight % To 100 weight %, preferably in the range of 0.2 weight % to 90 weight %, and more preferably in 1 to 80 weight % In the range of.

The example of inert carrier used in preparation includes solid carrier and liquid-carrier.The example of solid carrier include with The fine powder and particle of lower items: clay (such as kaolin, diatomite, bentonite, Fubasami clay or Emathlite), synthesis Hydrated silica, talcum, ceramics, other inorganic minerals (such as sericite, quartz, sulphur, active carbon, calcium carbonate or hydration two Silica) or chemical fertilizer (for example, ammonium sulfate, ammonium phosphate, ammonium nitrate, urea or ammonium chloride) etc.；And synthetic resin (example Such as, polyester resin such as polypropylene, polyacrylonitrile, polymethyl methacrylate and polyethylene terephthalate；Nylon resin (for example, nylon-6, nylon-11 and nylon -66)；Polyamide；Polyvinyl chloride, polyvinylidene chloride, vinyl chloride-propylene are total Polymers etc..

The example of liquid-carrier include water, alcohol (for example, methanol, ethyl alcohol, isopropanol, butanol, hexanol, benzylalcohol, ethylene glycol, Propylene glycol or phenoxetol)；Ketone (for example, acetone, methyl ethyl ketone or cyclohexanone)；Aromatic hydrocarbon is (for example, toluene, dimethylbenzene, second Benzene, detergent alkylate, phenyl xylyl ethane or methyl naphthalene)；Aliphatic hydrocarbon (for example, hexane, hexamethylene, kerosene or light oil)； Ester is (for example, ethyl acetate, butyl acetate, isopropyl myristate, ethyl oleate, diisopropyl adipate, two isobutyl of adipic acid Ester or propylene glycol methyl ether acetate)；Nitrile (such as acetonitrile or isobutyronitrile)；Ether is (for example, Di Iso Propyl Ether, Isosorbide-5-Nitrae-twoAlkane, second Glycol dimethyl ether, diethylene glycol dimethyl ether, dipropylene glycol monomethyl ether or 3-Methoxy-3-methyl-1-butanol)；Amide (for example, N, Dinethylformamide or DMAC N,N' dimethyl acetamide)；Halogenated hydrocarbons (for example, methylene chloride, trichloroethanes or carbon tetrachloride)；It is sub- Sulfone (for example, dimethyl sulfoxide)；Propene carbonate；With vegetable oil (for example, soybean oil or cottonseed oil).

The example of surfactant includes for example polyoxyethylated alkyl ether of nonionic surface active agent, polyoxyethylated alkane Base aryl ether and cithrol；With anionic surfactant such as alkylsulfonate, alkylbenzene sulfonate and alkane Base sulfate.

Other examples for being used for the adjuvant of preparation include adhesive, dispersing agent, colorant and stabilizer.Specific example packet Include casein, gelatin, polysaccharide (for example, starch, gum arabic, cellulose derivative and alginic acid), bentonite, water-soluble conjunction At polymer (for example, polyvinyl alcohol, polyvinylpyrrolidone and polyacrylic acid), PAP (acid isopropyl phosphoric acid salt), BHT (2, 6- di-t-butyl -4- cresols), the BHA (mixing of 2- tert-butyl -4- metoxyphenol and 3- tert-butyl -4- metoxyphenol Object).

It is of the invention for prevent and treat the method for harmful organism by the habitat lived to harmful organism or harmful organism, plant A effective amount of composition of the invention of the application such as object, soil is implemented.In the method for preventing and treating harmful organism of the invention, this Medicine type application for prevent and treat harmful organism of the composition of invention usually to prepare composition of the invention to it.

The specific example for applying composition of the invention includes to stem and leaf, flower, seedling or fringe (plant) application；To kind The soil (soil for cultivated plant) after soil or planting plants before planting plant is applied；To vegetable seeds (for example, Seed disinfection, seed impregnates or seed cladding) or bulb such as seed stem tuber application.Moreover, the compounds of this invention and Triflumezopyrim can be administered alone, and for example, by any in the compounds of this invention and triflumezopyrim Then another kind is applied to the seed or the bulb of the plant, Huo Zhe to the seed or bulb of plant by kind deposition For cultivating the seed of the plant or the soil of the bulb before or after plantation.

For be applied to plant stem and leaf, flower, seedling, fringe the specific example of method include for being applied to plant Surface method such as foliage applying and trunk application, and for when blooming (including before flowering, duration of flowering and open After flower) it is applied to colored or entirely plant method, and the method for being applied to fringe or entire plant in grain germination season.

Moreover, with the soil (soil for cultivated plant) being applied to before planting plants or after planting plants Method example include composition of the invention is applied to wait be protected from damage such as by harmful organism food crop Root method, and prevented by being absorbed composition of the invention from root and/or underground stem and being transferred to inside plants The method for controlling the harmful organism for the plant that eats food.

The specific example of application processing includes that the processing to plant hole (is sprayed in plant hole, the soil after handling plant hole Earth mixing), to the processing of plant bottom (soil mixing spraying to plant bottom, after handling plant bottom, to plant The irrigation of bottom, the processing in the seedling later period to plant substrate), processing (is sprayed in ditch dug with a plow, handles it in ditch dug with a plow in ditch dug with a plow Soil mixing afterwards), to the processing of plantation row (it is spraying to plantation row, to after plantation row processing soil mixing, growing It is interim spraying to plantation row), at seeding time to the processing of plantation row (at seeding time it is spraying to plantation row, at seeding time to plantation Soil mixing after row processing), spread fertilizer over the fields processing (overall soil surface is spraying, soil after spreading fertilizer over the fields processing mixes), be right The processing of skidding (lateral row), the processing of the water surface (to the application of the water surface, after irrigation to the application of the water surface), other soil Granule (is sprayed on leaf, is sprayed under tree crown or is setting around trunk, in soil surface in growth period by earth spraying treatment It is upper spraying, mix, be sprayed in sowing cave with surface soil, on the ground of ditch dug with a plow by spraying, between plant by spraying), other Irrigation regime (irrigate, in Seedling Stage irrigation, solution injection, the plant part irrigation to just on the ground, solution dropwise addition by soil Irrigate, chemigation), nursery box processing (, nursery box spraying to nursery box is irrigated, irrigated with chemical solution into nursery box), Seedlings nursing plate processing (spraying, seedlings nursing plate is irrigated and irrigated with chemical solution into seedlings nursing plate to seedlings nursing plate), seedbed processing are (to seedling Bed is spraying, seedbed is irrigated, it is spraying to the seedling bed after irrigation, impregnate seedling), nursery soil incorporation processing (mixed with nursery soil, It mixes with nursery soil, be sprayed before with soil covering at seeding time prior to seeding, being mixed with mulching soil and other are handled It (is mixed with culture soil, (plowing under) is turned down in ploughing, mix with surface soil, the soil that goes out with the place that raindrop are fallen Granule is sprayed on flowers, mixes with pulpous state fertilizer by earth mixing, the processing of planting location).

The example of the seed or bulb that are applied to plant can also be by being applied to the plant for composition of the invention Seed or bulb are implemented.The kind subrepresentation of plant described herein is in the culture being seeded into soil or for cultivating seed The seed of the plant of state before base, and bulb described herein indicates to be in plantation to soil or for cultivation Plate-like stem, bulb, rhizomes, stem tuber, tuberosity, seed stem tuber and the tuberosity root of the plant of state before in culture medium. For the example packet by the way that composition of the invention to be administered in the seed or bulb of plant to the method for preventing and treating harmful organism It includes and composition of the invention is applied directly to the seed or bulb to be protected from damaging the plant such as absorbed by harmful organism In method；The nocuousness for absorbing seed is prevented and treated with by using composition of the invention near the seed or bulb of plant The method of biology；With the inside by composition of the invention being infiltrated through and being transferred to plant from the seed or bulb of plant Method to prevent and treat the harmful organism for absorbing plant.Composition of the invention is applied to the method for the seed or bulb of plant Example includes spraying treatment, spray treatment, immersion treatment, impregnation, coating processing, coating problems and particle coating processing.

When composition of the invention is for when preventing and treating harmful organism, administration dosage can to depend on administration time, application ground Point, method of application etc. broadly change.The total amount of the compounds of this invention and triflumezopyrim are usually 1 to 10,000g/ 10,000m²In the range of.When composition of the invention is configured to missible oil, wettable powder, flowable formulation etc., the present invention Compound and triflumezopyrim are usually applied by the way that they are diluted with water so that the compounds of this invention and The total concentration of triflumezopyrim is in the range of 0.01 to 10,000ppm.The granular preparation or dirt shape preparation situations such as Under, these preparations are usually employed without as it is to be diluted.

Moreover, composition of the invention can be handled by nursery box to be made when composition of the invention is applied to rice With.It can be for from the sowing time to transplant time by the time that nursery box handles application composition of the invention.Moreover, this hair Bright composition can be used for direct sowing cultivation or the implanting and cultivating of rice.When composition of the invention is used for directly rice Connect sowing cultivation when, composition of the invention can on the rice field after irrigation directly sow before, on the rice field after irrigation It applies, and is also possible to directly after sowing, after directly being sowed before directly being sowed on dry rice field or on dry rice field Before planting to after planting 21 days time.When composition of the invention is used for implanting and cultivating for rice, rice can be with Be after this, and the time applied can be transplanting before to after transplanting 21 days time.

Composition of the invention includes that harmful arthropod is such as harmful to the example of its harmful organism with some effect Insect and harmful acarid.The specific example of the harmful organism includes following.

Semiptera harmful organism:

Delphacidae (Delphacidae) is (for example, small brown rice planthopper (Laodelphax striatellus), brown paddy plant hopper (Nilaparvata lugens) or Sogatellafurcifera (Sogatella furcifera)),

Deltocephalidae (Deltocephalidae) is (for example, rice green leafhopper (Nephotettix cincticeps), two Point rice green leafhopper (Nephotettix virescens), tea green leafhopper (Empoasca onukii)),

Aphidiadae (Aphididae) is (for example, cotten aphid (Aphis gossypii), black peach aphid (Myzus persicae), brevicoryne brassicae (Brevicoryne brassicae), different spiraea aphid (Aphis spiraecola), potato aphid (Macrosiphum Euphorbiae), Aulacorthumsolani (Aulacorthum solani), rhopalosiphum padi (Rhopalosiphum padi), Toxopteracitricidus (Toxoptera citricidus) or mealy plum aphid (Hyalopterus pruni)),

Pentatomiddae (Pentatomidae) is (for example, Nezaraantennata (Nezara antennata), Riptortusclavetus (Riptortus Clavetus), Riptortusclavetus (Riptortus clavetus), middle Leptocorisa spp (Leptocorisa chinensis), wedge angle two Star stinkbug (Eysarcoris parvus) or Halyomorphamista (Halyomorpha mista)),

Aleyrodidae (Aleyrodidae) is (for example, greenhouse whitefly (Trialeurodes vaporariorum), sweet potato whitefly (Bemisia tabaci), citrus aleyrodid (Dialeurodes citri), tangerine pierce aleyrodid (Aleurocanthus spiniferus))。

Lepidoptera (Lepidoptera) harmful organism:

Pyralidae (Pyralidae) is (for example, striped rice borer (Chilo suppressalis), yellow rice borer (Tryporyza Incertulas), cnaphalocrocis medinalls guenee (Cnaphalocrocis medinalis), Notarchaderogata (Notarcha Derogata), Plodiainterpunctella (Plodia interpunctella), Ostrinia furnacalis (Ostrinia furnacalis), Hellula undalis (Hellula undalis) or bluegrass snout moth (Pediasia teterrellus)),

Noctuidae (Noctuidae) is (for example, Spodoptera litura (Spodoptera litura), Beet armyworm (Spodoptera exigua), mythimna separata (Pseudaletia separata), lopper worm (Mamestra brassicae), Black cutworm (Agrotis ipsilon), Plusianigrisigna (Plusia nigrisigna), Trichoplusiaspp (Trichoplusia spp.), Heliothis (Heliothis spp.) or Helicoverpa (Helicoverpa spp.)),

Sulfur butterfly (Pieridae) (for example, cabbage butterfly (Pieris rapae)),

Tortricidae (Tortricidae) is (for example, oriental fruit months (Grapholita molesta), eating-core bean worm (Leguminivora glycinivorella), Matsumuraesesazukivora (Matsumuraeses azukivora), adoxophyes moth (Adoxophyes orana fasciata), tea steinernema (Adoxophyes honmai.), Homonamagnanima (Homona Magnanima), Archipsfuscocupreanus (Archips fuscocupreanus) or codling moth (Cydia Pomonella)),

Gracilariidae (Gracillariidae) is (for example, Caloptiliatheivora (Caloptilia theivora) or Phyllonorycterringoneella (Phyllonorycter ringoneella)),

Carposinidae (Carposinidae) (for example, peach column fruit moth (Carposina niponensis)),

Lyonetid section (Lyonetiidae) (for example, Lyonetiaspp (Lyonetia spp.)),

Lymantriidae (Lymantriidae) is (for example, Euproctis (Lymantria spp.) or Euproctis (Euproctis Spp.)),

Yponomeutidae (Yponomeutidae) (for example, diamondback moth (Plutella xylostella)),

Gelechidae (Gelechiidae) is (for example, Pectinophora gossypiella (Pectinophora gossypiella) or potato wheat Moth (Phthorimaea operculella)),

Arctiidae (Arctiidae) (for example, fall webworms (Hyphantria cunea))；

Rain moth section (Tinea) (for example, casemaking clothes moth (Tinea translucens)).

Thysanoptera (Thysanoptera) harmful organism:

Ying Chi section (Thysanopterae) is (for example, Frankliniella occidentalis (Frankliniella occidentalis), south Huang The yellow hard thrips (Scirtothrips dorsalis) of thrips (Thrips parmi), tea, onion thrips (Thrips tabaci) or Beautiful flower thrips (Frankliniella intonsa)).

Diptera (Diptera) harmful organism:

Anthomyiidae (Anthomyiidae) is (for example, delia platura (Delia platura) or green onion ground Hylemyia Platura Meigen (Delia Antiqua)),

Agromyzidae (Agromyzidae) is (for example, Japanese rice lyonetid (Agromyza oryzae), barley hair eye ephydrid (Hydrellia griseola), vegetable leafminer (Liriomyza sativae), Liriomyza trifolii (Liriomyza Trifolii) or pea coloured silk dives fly (Chromatomyia horticola)),

Stem maggot section (Chloropidae) (for example, ricestem-fly (Chlorops oryzae)),

Tephritidae (Tephritidae) is (for example, melon widow's hair on the neck trypetid (Dacus cucurbitae) or Mediterranean fruitfly (Ceratitis capitata)), and

Drosophilidae (Drosophilidae).

Coleoptera (Coleoptera) harmful organism:

Chrysomelidae (Chrysomelidae) is (for example, diabroticavirgifera (Diabrotica virgifera Virgifera), 11 asterophyllite first of cucumber (Diabrotica undecimpunctata howardi)),

Scarabaeidae (Scarabaeidae) is (for example, Anomalacuprea (Anomala cuprea), polychrome different beetle (Anomala rufocuprea) or Japan popillia flavosellata fairmaire (Popillia japonica)),

Culculionidae (Curculionidae) is (for example, sitophilus zea-mais (Sitophilus zeamais), Lissorhoptrusoryzophilus (Lissorhoptrus oryzophilus), Lissorhoptrus oryzophilus Kuschel (Echinocnemus squameus), anthonomus grandis (Anthonomus Grandis) or hunt weevil (Sphenophorus venatus)),

Paragraph (Tenebrionidae) is (for example, yellow meal worm (Tenebrio molitor) or red flour beetle (Tribolium castaneum)),

Chrysomelidae (Chrysomelidae) is (for example, Oulema oryzae (Oulema oryzae), aulacophora femoralis (Aulacophora femoralis), phyllotreta striolata (Phyllotreta striolata) or colorado potato bug (Leptinotarsa decemlineata)),

Epilachna genus (Epilachna) is (for example, ladybug of eggplant 28 stars (Epilachna Vigintioctopunctata)),

Scolytidae (Scolytidae) is (for example, Lyctus brunneus Stephens (Lyctus brunneus) or vertical pit cutting pin small moth (Tomicus Piniperda)),

Bostrichidae (Bostrichidae),

Ptinidae (Ptinidae),

Cerambycidae (Cerambycidae) (for example, Anoplophoramalasiaca (Anoplophora malasiaca)),

Elateridae (Elateridae) (click beetle category (Agriotes spp.) or wireworm (Limonius spp.)), and

Malicious rove beetle (Paederus fuscipes).

Above-mentioned harmful organism further includes the harmful organism population that resistance is obtained for traditional medicament, and therefore originally The composition of invention is effective for the resistant population.

The present composition can include following to the example for the plant that it is applied.

Crop: corn, rice, wheat, barley, rye, oat, sorghum, cotton, soybean, peanut, buckwheat, beet, rape Seed, sunflower, sugarcane and tobacco etc.；

Vegetables: solanaceous vegetable (eggplant, tomato, pimento, capsicum and potato etc.), cucurbit class vegetables (cucumber, pumpkin, Zucchini, watermelon, muskmelon and pumpkin etc.), cruciate flower class vegetables (japanese radish, white radishes, horseradish, root-mustard, great Bai Dish, cabbage, leaf mustard, cabbage and cauliflower etc.), composite family class vegetables (fructus arctii, crowndaisy chrysanthemum, globe artichoke and lettuce etc.), lily class Vegetables (shallot, onion, garlic and asparagus), umbrella shape class vegetables (carrot, parsley, celery and parsnip etc.), Chenopodiaceae class vegetable Dish (spinach and leaf beet etc.), lip shape class vegetables (purple perilla, peppermint and sweet basil etc.), strawberry, sweet potato, glutinous rice yam and taro Deng；

Flowering plant；

Foliage plant；

Turfgrass；

Fruit: pomaceous fruits (apple, pears, Japanese pear, pawpaw He Wen Quince etc.), (peach, plum, peach refute Lee, Japanese plum to kernel approaches (Prunus mume), cherry, apricot and Lee etc.), mandarin orange fruit (satsuma orange, lemon, comes lemon and grape fruit etc. at tangerine), nut fruits (chestnut, English walnut, hazel, almond, pistachio, cashew nut and Queensland nut etc.), berries (cowberry, Cranberry, blackberry, blueberry and red raspberry Deng), grape, Japanese persimmon, olive, loquat (Japanese plum), banana, coffee, date palm and coconut etc.；And

Other trees in addition to fruit tree: tea, mulberry, plant of admiring the beauty of flowers, shade tree (Ash, birch, Lai wood, eucalyptus, ginkgo (ginkgo Biloba), cloves, maple, oak (quercus), poplar, cercis, Chinese sweet gum (Liquidambar formosana), plane tree, beech Tree, Japanese arbor-vitae (Thuja standishii), fir, siebold hemlock, Chinese juniper, pine, dragon spruce and Japanese yew (Taxus Cuspidate)) etc..

Above-described plant can be the plant bred by hybridization technique.

That is, being to have the plant of hybrid vigour (in general, for example, it causes yield latent by the plant that hybridization technique is bred The enhancing of power and to biology and abiotic stress factor resistance improvement).

Aforementioned " plant " may include the plant for having assigned resistance by Genetic Recombination.

For example, above-described plant further includes having the plant resistant to herbicide, the herbicide includes HPPD inhibitor is for example differentAzoles humulone (isoxaflutole)；ALS inhibitor such as imazethapyr (imazethapyr) and thiophene Sulphur is grand (thifensulfuron methyl)；EPSP inhibitor；Glutamine synthetase inhibitor；Brominal (bromoxynil)；Dicamba (dicamba) etc., the resistance passes through classical propagation method or genetic modification technique assigns.

Above-described plant may include being generated by using genetic modification technique, and selection can be synthesized by having become The plant of (such as Bacillus) such as property toxin.

In addition, above-described plant includes having with such as above-mentioned Herbicid resistant, Pest-resistant, Disease Resistance etc. The strain (feature is assigned using classical reproduction technique or genetic modification technique) of the feature of relevant two or more types, and (property will be by that will have identical or different kinds of properties for the strain of maternal possessed property with two or more types Genetic modification plant hybridization and assign).The example of such plant includes Smart stax (registered trademark).

In the present compositions, the compounds of this invention and triflumezopyrim ratio are by weight usually 100 : in the range of 1 to 1: 100, and preferably in the range of 10: 1 to 1: 10.

Composition of the invention can also be comprising one or more selected from the compound organized such as (A) mentioned below.

(A) group: the group being made of following compound: clothianidin (clothianidin), dinotefuran (dinotefuran), Diacloden (thiamethoxam), imidacloprid (imidacloprid), Nitenpyram (nitenpyram), thiacloprid (thiacloprid), Fipronil (fipronil), ethiprole (ethiprole), Etofenprox (etofenprox), fluorine silicon chrysanthemum Ester (silafluofen), Rynaxypyr (chlorantraniliprole), bromine cyanogen insect amide (cyantraniliprole), cartap (cartap), fluorine pyrrole furanone (flupyradifurone), pymetrozine (pymetrozine), isotianil (isotianil), Fluoxastrobin (azoxystrobin), orysastrobin (orysastrobin), probenazole (probenazole), tiadinil (tiadinil), tricyclazole (tricyclazole), cough up Quinoline ketone (pyroquilon), double chlorine zarilamid (diclocymet), ferimzone (ferimzone), phthalide (phthalide), spring Thunder mycin hydrochloride hydrate (kasugamycin hydrochloride hydrate), tebufloquin, Pencycuron (pencycuron), valida (validamycin), hexaconazole (hexaconazole), Fu Duoning (flutolanil), ring Propionyl bacterium amine (carpropamid), fluopicolide (furametpyr), fluorine azoles bacterium benzene (penflufen) and tolprocarb.

Combined example includes following.

" any one of the compounds of this invention 1 to 481 ", triflumezopyrim and isotianil (isotianil) Combination；

" any one of the compounds of this invention 1 to 481 ", triflumezopyrim and orysastrobin (orysastrobin) combination；

" any one of the compounds of this invention 1 to 481 ", triflumezopyrim and probenazole (probenazole) Combination；

" any one of the compounds of this invention 1 to 481 ", triflumezopyrim and tricyclazole (tricyclazole) Combination；

" any one of the compounds of this invention 1 to 481 ", triflumezopyrim and double chlorine zarilamid (diclocymet) combination；

" any one of the compounds of this invention 1 to 481 ", triflumezopyrim and ring propionyl bacterium amine (carpropamid) combination；

" any one of the compounds of this invention 1 to 481 ", triflumezopyrim and tiadinil (tiadinil) Combination；

" any one of the compounds of this invention 1 to 481 ", triflumezopyrim and pyroquilon (pyroquilon) Combination；

The combination of " any one of the compounds of this invention 1 to 481 ", triflumezopyrim and tolprocarb；

" any one of the compounds of this invention 1 to 481 ", triflumezopyrim and fluopicolide (furametpyr) Combination；

" any one of the compounds of this invention 1 to 481 ", triflumezopyrim and fluorine azoles bacterium aniline (penflufen) Combination；

" any one of the compounds of this invention 1 to 481 ", triflumezopyrim, isotianil (isotianil) and The combination of fluopicolide (furametpyr)；

" any one of the compounds of this invention 1 to 481 ", triflumezopyrim, isotianil (isotianil) and The combination of fluorine azoles bacterium aniline (penflufen)；

" any one of the compounds of this invention 1 to 481 ", triflumezopyrim, probenazole (probenazole) and The combination of fluopicolide (furametpyr)；

" any one of the compounds of this invention 1 to 481 ", triflumezopyrim, probenazole (probenazole) and The combination of fluorine azoles bacterium aniline (penflufen)；

" any one of the compounds of this invention 1 to 481 ", triflumezopyrim, tricyclazole (tricyclazole) and The combination of fluopicolide (furametpyr)；

" any one of the compounds of this invention 1 to 481 ", triflumezopyrim, tricyclazole (tricyclazole) and The combination of fluorine azoles bacterium aniline (penflufen)；

" any one of the compounds of this invention 1 to 481 ", triflumezopyrim, tiadinil (tiadinil) and fluorine The combination of pyrrole bacterium amine (furametpyr)；

" any one of the compounds of this invention 1 to 481 ", triflumezopyrim, tiadinil (tiadinil) and fluorine The combination of azoles bacterium aniline (penflufen)；

" any one of the compounds of this invention 1 to 481 ", triflumezopyrim, pyroquilon (pyroquilon) and fluorine The combination of pyrrole bacterium amine (furametpyr)；

" any one of the compounds of this invention 1 to 481 ", triflumezopyrim, pyroquilon (pyroquilon) and fluorine The combination of azoles bacterium aniline (penflufen)；

" any one of the compounds of this invention 1 to 481 ", triflumezopyrim, tolprocarb and fluopicolide (furametpyr) combination；

" any one of the compounds of this invention 1 to 481 ", triflumezopyrim, tolprocarb and fluorine azoles bacterium aniline (penflufen) combination；

Embodiment

Hereinafter, the present invention is explained in greater detail by using preparation example and test example.However, the present invention should not limit to In these embodiments.Unless otherwise indicated, " part " expression " parts by weight ".

Firstly, description preparation example.

Preparation example 1

Any one of the compounds of this invention 1 to 481 by five (5) parts, 10 parts of triflumezopyrim, 35 parts The mixing of the mixture and water of white carbon black and polyoxyethylene alkyl ether ammonium sulfate (weight ratio 1: 1) is to be made as total weight 100 parts of part obtain each preparation followed by wet grinding fine grinding.

Preparation example 2

Any one of the compounds of this invention 1 to 481 by ten (10) parts, 2 parts of triflumezopyrim, 1.5 parts Sorbitan trioleate, 28 parts of the solution containing 2 parts of polyvinyl alcohol mix and wet grinding are utilized to grind, then to mixing Solution and 0.1 part of aluminium-magnesium silicate containing 0.05 part of xanthan gum are added in object, 90 parts to be made as total weight parts.To mixed It closes in object, 10 parts of propylene glycol is added, and stir the mixture for and mix, obtain each preparation.

Preparation example 3

Any one of the compounds of this invention 1 to 481 by ten (10) parts, 10 parts of triflumezopyrim, 3 parts The synthetic hydrated silicon oxide of calcium lignosulfonate, 2 parts of dodecyl sodium sulfate and remaining part well grinds and mixes, and obtains 100 Each wettable powder of part.

Preparation example 4

Any one of the compounds of this invention 1 to 481 of (1) part, 0.5 part of triflumezopyrim, 1 part is added Synthetic hydrated silicon oxide fine powder, 2 parts of calcium lignosulfonate, 30 parts of bentonite and remaining part kaolinton and mixing. Then, into mixture, suitable water is added, and stir the mixture for, forced air drying is granulated and passed through using granulator, Obtain 100 parts of each granular preparation.

Preparation example 5

Any one of 2 parts of the compounds of this invention 1 to 481 by 100 (100) parts, 0.75 part of triflumezopyrim, 2 parts of isotianils (isotianil), 1 part of synthetic hydrated silicon oxide, 2 parts of calcium lignosulfonates, 30 parts of bentonite and remaining part The mixture of kaolinton mix with being fully ground, and water is added thereto, and mixture is mediated very well, and be granulated and dry It is dry, obtain 100 parts of each granular preparation.

Preparation example 6 to 15

In addition to using respective compound described in [Table A] and its dosage to replace 2 parts of isotianil (isotianil), each granular preparation is obtained according to the similar program of preparation example 5.

[Table A]

Next, describing the application examples of composition of the invention to vegetable seeds.

Application examples 1

By using rotostatic seed treaters (seed dresser (seed dresser), by Hans-Ulrich Hege GmbH Manufacture), by each preparation of the preparation of the method according to preparation example 1 or 2 with the amount of the dry sorghum seeds of 200ml/100kg For smearing processing, processed each seed is obtained.

Moreover, oxabetrinil (oxabetrinil) is added into each preparation 200mL obtained in above-mentioned preparation 180g or fluxofenim (fluxofenim) 40g, and resulting preparation can be used for the painting in the sorghum seeds of above-mentioned drying Processing is smeared, processed each seed is obtained.

Application examples 2

By using rotostatic seed treaters (seed dresser (seed dresser), by Hans-Ulrich Hege GmbH Manufacture), each preparation of the preparation of the method according to preparation example 1 or 2 is used with the amount of the dry corn seed of 40ml/10kg In smearing processing, processed each seed is obtained.

Application examples 3

By each wettable powder of the preparation of the method according to preparation example 3 with the dry corn seed of 50g/10kg Amount is used for pulvis coating processing, obtains processed each seed.

Application examples 4

By using rotostatic seed treaters (seed dresser (seed dresser), by Hans-Ulrich Hege GmbH Manufacture), each preparation of the preparation of the method according to preparation example 1 or 2 is used with the amount of the dry soya seeds of 20ml/10kg In smearing processing, processed each seed is obtained.

Application examples 5

By using rotostatic seed treaters (seed dresser (seed dresser), by Hans-Ulrich Hege GmbH Manufacture), by each wettable powder of the preparation of the method according to preparation example 3 with the amount of the dry soya seeds of 30g/10kg For pulvis coating processing, processed each seed is obtained.

Application examples 6

By using rotostatic seed treaters (seed dresser (seed dresser), by Hans-Ulrich Hege GmbH Manufacture), each preparation of the preparation of the method according to preparation example 1 or 2 is used with the amount of 50ml/10kg dried cotton seed In smearing processing, processed each seed is obtained.

Application examples 7

By using rotostatic seed treaters (seed dresser (seed dresser), by Hans-Ulrich Hege GmbH Manufacture), by each preparation of the preparation of the method according to preparation example 1 or 2 with the amount of 150ml/10kg dried grape seed For smearing processing, processed each seed is obtained.

Application examples 8

By using rotostatic seed treaters (seed dresser (seed dresser), by Hans-Ulrich Hege GmbH Manufacture), each preparation of the preparation of the method according to preparation example 1 or 2 is used with the amount of the dry rice paddy seed of 20ml/10kg In smearing processing, processed each seed is obtained.

Application examples 9

By using rotostatic seed treaters (seed dresser (seed dresser), by Hans-Ulrich Hege GmbH Manufacture), by each wettable powder of the preparation of the method according to preparation example 3 with the amount of the dry rice paddy seed of 60g/10kg For pulvis coating processing, processed each seed is obtained.

Next, showing effect of the invention by following tests example.

Test example 1

Respectively by the compounds of this invention of each 1mg 3,15,19,20,48,50,72,81,85,99,130,421,444, 445,464 and 467 or triflumezopyrim is dissolved into the dimethylbenzene, dimethylformamide and surfactant (commodity of 10 μ L Name: Sorpol 3005X is manufactured by TOHO CHEMICAL INDUSTRY CO.LTD) mixed solution of (4: 4: 1 (volume ratio)) In.Thereto be added containing 0.02% (v/v) spreading agent (trade name: Sindain, by Sumitomo Chemical Co (Sumitomo Chemical Company, Limited) manufacture) water, to be made as each in what is indicated in [table 21] to [table 22] A normal concentration, to prepare each test chemical solution.

The leaf dish (length 1.5cm) of the cotyledon of cucumber (Cucumis sativus) is put into 24 orifice plates (by Becton Dickinson manufacture) each hole in and every 1 hole discharge 2 cotten aphids (Aphis gossypii) aptery adult and 8 Cotten aphid larva, and with the ratio spray testing chemical solution in 20 holes μ L/1, it is referred to as processing group.

And replace test chemical solution, by 20 μ L contain 0.02% (v/v) spreading agent (trade name: Sindain, by live The manufacture of friendly Chemical Co., Ltd.) water spray into hole, be referred to as untreated fish group.

After being air-dried, by the top of microplate with breathable film piece (ProductName: AeraSeal, by Excel Scientific Inc. manufacture) covering, and 5 days after insect release, investigate the quantity of the surviving insects in each hole.

Respectively, it for each treatment value of processing group or untreated fish group, is calculated by the following formula.

Formula (1)

Treatment value (%)={ 1- (Tai)/(Cai) } × 100

Wherein the symbology in the formula is described below.

Cai: in untreated fish group investigate when surviving insects quantity；

Tai: in processing group investigate when surviving insects quantity；

As a result, as shown in [table 21] into [table 22], separately include the compounds of this invention 3,15,19,20, 48, the composition of the invention of 50,72,81,85,99,130,421,444,445,464 and 467 and triflumezopyrim Show excellent preventing efficiency.

Here, respectively, the triflumezopyrim or this hair observed in being similar to the test that above-mentioned experiment carries out Bright compound individually each treatment value in following display.For triflumezopyrim, 4 (concentration 0.1ppm) and 30 (concentration 1ppm)；For the compounds of this invention 15,28 (concentration 1ppm)；For the compounds of this invention 20,12 (concentration 0.01ppm)；For The compounds of this invention 72,32 (concentration 10ppm)；For the compounds of this invention 444,32 (concentration 1ppm)；For chemical combination of the present invention Object 445,30 (concentration 0.1ppm) and 37 (concentration 1ppm).

[table 21]

[table 22]

Industrial applicibility

The present invention can prevent and treat harmful organism.

Claims (6)

1. a kind of for preventing and treating the composition of harmful organism, the composition for preventing and treating harmful organism includes:

The compound indicated by formula (1):

Wherein,

A¹Expression-NMe- or oxygen atom,

A²Expression=N- ,=N (→ O)-or=CH-,

Q expression=N-,

R¹Indicate C1-C6 alkyl,

R²And R⁴Respectively indicate hydrogen atom,

R³Indicate the C1-C3 alkyl or hydrogen atom optionally with one or more halogen atoms,

R⁵Indicate C1-C3 the alkyl ,-OR optionally with one or more halogen atoms¹⁰Or-S (O)_mR¹⁰,

R⁶Expression-NR¹⁰R¹¹Or hydrogen atom,

R¹⁰And R¹¹It is same or different to each other, and respectively indicates the C1-C3 alkyl optionally with one or more halogen atoms,

M indicates 0,1 or 2 independently of one another, and

N expression 2, and

2,4- dioxo -1- (5- Pyrimidylmethyl) -3- [3- (trifluoromethyl) phenyl] -2H- pyrido [1,2-a] pyrimidineIt is interior Salt,

The wherein compound and 2,4- dioxo -1- (5- Pyrimidylmethyl) -3- [3- (trifluoromethyl) indicated by formula (1) Phenyl] -2H- pyrido [1,2-a] pyrimidineThe ratio of inner salt is by weight in the range of 100:1 to 1:100.

2. according to claim 1 for preventing and treating the composition of harmful organism, wherein A¹Expression-NMe-.

3. according to claim 1 for preventing and treating the composition of harmful organism, wherein A¹Indicate oxygen atom.

4. it is according to any one of claim 1 to 3 for preventing and treating the composition of harmful organism, wherein described by formula (1) The compound and 2,4- dioxo -1- (5- Pyrimidylmethyl) -3- [3- (trifluoromethyl) phenyl] -2H- pyrido [1,2- of expression A] pyrimidineThe ratio of inner salt is by weight in the range of 10:1 to 1:10.

5. a kind of method for preventing and treating harmful organism, the habitat that the method includes living to harmful organism or harmful organism It applies a effective amount of according to any one of claim 1 to 4 for preventing and treating the composition of harmful organism.

6. a kind of method for preventing and treating harmful organism, the method includes to plant, vegetable seeds, bulb or for cultivating The soil application for stating plant is a effective amount of according to any one of claim 1 to 4 for preventing and treating the combination of harmful organism Object.