WO1997000854A1

WO1997000854A1 - Amide compound, process for producing the same, and insecticidal/miticidal drug

Info

Publication number: WO1997000854A1
Application number: PCT/JP1995/001224
Authority: WO
Inventors: Yasuo Yamada; Takashi Kishimoto; Tatsumi Suzuki; Michihiko Matsuda; Renpei Hatano; Takao Iwasa
Original assignee: Nippon Soda Co., Ltd.
Priority date: 1995-06-20
Filing date: 1995-06-20
Publication date: 1997-01-09
Also published as: AU2683595A

Abstract

An amide compound represented by general formula (I), a process for producing the same, and an insecticidal/miticidal drug which works without fail and is safely usable, wherein X represents hydrogen, halogen, alkyl, alkoxy, phenyl, phenoxy, alkylthio, phenylthio, nitro, amino, cyano, etc.; n represents an integer of 1 to 5; Y represents halogen, cyano, alkyl, alkoxy, etc.; m represents an integer of 1 to 5; Z represents halogen, alkylsulfonyloxy, phenylsulfonyloxy, acetoxy, benzoyloxy, alkoxycarbonyloxy, carbamoyloxy, thiocarbamoyloxy, sulfamoyloxy, phosphonyloxy, etc.; A represents ethylene; and R represents hydrogen or benzoyl.

Description

Amidamide compounds, their manufacturing methods and insecticides and acaricides Technical fields:

The present invention relates to a novel amide compound, a production method thereof, and a pesticide. Background art:

Many insecticides and acaricides have been used in the past, but their efficacy was insufficient, their use was limited due to drug resistance problems, and phytotoxicity and contamination of plants occurred. In addition, because of their high toxicity to humans and fishes, many of them are not necessarily satisfactory control agents. Therefore, there is a demand for the development of a drug that can be used safely with few such disadvantages.

An object of the present invention is to provide a harmful organism controlling agent which can be synthesized industrially advantageously, has a certain effect and can be used safely.

Disclosure of the invention:

The present invention provides a compound represented by the formula (I):

Z-A 0

[In the formula, X is hydrogen, halogen, phenyl, an optionally substituted phenyl group}, an alkyl group optionally substituted with a phenyl, a substituted or unsubstituted phenyl group. An optionally substituted alkoxy group, an optionally substituted phenyl group, an optionally substituted phenyl group, an optionally substituted alkylthio group, an optionally substituted phenylthio group, a nitro group, an optionally substituted It represents a diamino group, a cyano group, an alkylsulfonyloxy group, an optionally substituted pyridyloxy group or an optionally substituted phenylsulfinyl group.

n represents an integer of 1 to 5, and when it is 2 or more, X may be different.

Y is halogen, cyano, an optionally substituted alkyl group or an optionally substituted Represents an alkoxy group, an alkylthio group, an amino group which may be substituted, or a nitrogen atom.

m represents an integer of 1 to 5, and when it is 2 or more, Y may be different.

Z is a hydroxyl group, a halogen, an optionally substituted alkylsulfonyloxy group, an optionally substituted phenylsulfonyloxy group, an optionally substituted acetyloxy group, an optionally substituted benzoyloxy group, or an optionally substituted Represents an alkoxycarbonyloxy group, an optionally substituted rubamoyloxy group, an optionally substituted thiocarbamoyloxy group, an optionally substituted sulfamoyloxy group or an optionally substituted phosphonylooxy group.

A represents ethylene which may be substituted.

R represents hydrogen or a benzoyl group which may be substituted. The amide compound represented by the formula, its production method and insecticide and acaricide.

In the present invention, examples of the group that substitutes the phenyl group of X include hagen, C,-(; alkyl,-"haloalkyl," alkoxy and the like.

Examples of the group that substitutes the phenylalkoxy group for X include halogen and alkyl.

Examples of the group that substitutes the phenyl group for X include halogen, da alkyl, C alkoxy, "haloalkyl, aralkyloxy and the like.

Examples of the group that substitutes the phenoxy group for X include halogen, C, _-l; alkyl,

C.- ,; alkoxy, C haloalkyl, aralkyloxy and the like.

Examples of the group that substitutes the fluorothio group for X include halogen.

Examples of the group which substitutes the pyridyloxy group and the phenylsulfinyl group of X include halogen, C,-"alkyl, C" haloalkyl and the like.

Examples of the group for substituting the alkyl group of Υ are halogen and the like.

Examples of the group that substitutes the amino group of X and Υ include C,-, and alkyl. Examples of the group that substitutes the alkylsulfonyloxy group of Ζ include halogen and the like.

Examples of the group for substituting the phenylsulfonyloxy group in Ζ include alkyl and the like. Examples of the group that substitutes the acetyl group of Z include halogen.

Examples of the group that substitutes for the benzoyloxy group of z include halogen.

Examples of the group that substitutes the rubamoyloxy group of Z include, for example, phenyl and phenyl which may be substituted with halogen.

The group that substitutes the thiocarbamoyloxy group for Z is, for example, alkylaryl.

Examples of the group that substitutes the sulfamoyloxy group for Z include C (; alkyl and the like.

Examples of the group that substitutes the phosphonyoxy group of Z include C,-(; alkyl and the like.

Examples of the group that substitutes ethylene for A include “alkyl, haloalkyl, and phenyl.

Examples of the group that substitutes benzyl in R include halogen.

The production method of the compound of the present invention is as follows.

(a)

A— 0 H

[In the formula, W represents a leaving group such as a halogen, a hydroxyl group, a monovalent S〇2R, (R, represents an alkyl such as methyl, or a substituted phenyl such as a ρ-tolyl group.) , A, m, n, X, and Y have the same meaning as described above. ]

The reaction is water, benzene, tetrahydrofuran, acetonitrile, dichloromethane In an inert solvent such as N, N-dimethylformamide, if necessary, use a dehydrochlorinating agent such as triethylamine, pyridine, sodium hydroxide or the like, or if necessary, to a concentrated sulfuric acid or dicyclohexane. Using a dehydrating agent such as xylcarposimide, the reaction is carried out for 30 minutes to several 10 hours at a temperature ranging from 120 ° C to the boiling point of the solvent used.

(b)

A- OH

[Wherein, A, m, n, X, Y, and Z have the same meaning as described above. ]

The reaction is carried out in an inert solvent such as benzene, tetrahydrofuran, getyl ether, dichloromethane, acetate nitrile, etc., in a solvent such as thionyl chloride, oxychloride, phosphorus trichloride, and phosphorus pentachloride. Halogenating agent, or R ₂ S 02 C 1, RHC 0 C 1, R, P 0 C 1, or R ", NC 0 (isocyanates), R« NCS (isocyanates) (R ₂ , R,, R ₄ , R,, R,; are an optionally substituted alkyl group, an optionally substituted alkoxy group, an optionally substituted amino group, and an optionally substituted And, if desired, a base such as triethylamine, pyridin, sodium hydroxide, sodium carbonate, etc., at 120 ° C. It is carried out for 30 minutes to several 10 hours up to the boiling point of the solvent used.

In any case, after completion of the reaction, the desired product can be obtained by performing ordinary post-treatment.

The structure of the compound of the present invention was determined from IR, NMR, MASS and the like. BEST MODE FOR CARRYING OUT THE INVENTION

Next, the present invention will be described in more detail with reference to examples.

Example 1

3- (2-Bromophenyl) -13-amino-1-propanol (10.lg) and 4.4 g of triethylamine are dissolved in 50 ml of tetrahydrofuran and stirred with ice-cooling. Below, 2, 6-difluorene benzoyl alkite 8. lg was added and reacted at room temperature. One hour later, the reaction solution was poured into ice water, extracted with ethyl acetate, washed with water, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The obtained crystals are washed with getyl ether and separated by filtration to obtain the desired N— [1- (2-promophenyl) _3—hydroxypropyl] —2,6-dibenzo-benzamide (Compound No. 9) 1) 3.5 g were obtained. m. p. [1 15 _ 1 17 ° C]

Example 2

N-[1-(2-bromophenyl) 1 3-hydroxypropyl]-2,6-difluorobenzamide 1 2.9 g is dissolved in 80 ml of benzene, and 5 g of thionyl chloride is refluxed under reflux. Was added dropwise over a period of 10 minutes, and the mixture was further reacted for 30 minutes. After cooling the reaction mixture, the precipitated crystals are washed with n-hexane to obtain the desired N— [1- (2-bromophenyl) —3—cyclopropyl] —2, 6— Difluobenzoamide (Compound No. 11) (13.0 g) was obtained. m. p. [1 8 3-18 5 ° C] Example 3

N- [11- (4-chlorophenyl) 13-hydroxypropyl] 1-2,6-difluorobenzamide 0.2 g, and triethylamine 0.1 lg to tetrahydrofuran 1 The reaction mixture was dissolved in O ml, and 0.1 g of methanesulfonyl chloride was added thereto under ice-cooling and stirring, and reacted at room temperature. Two hours later, the reaction solution was poured into ice water, extracted with ethyl acetate, washed with water, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The obtained crystals are washed with getyl ether and separated by filtration to obtain the desired N- [1- (4-chlorophenyl) -13- (methylsulfonyloxy) propyl] -12,6-difluorobenzamine. (Compound No. 2) 0.25 g was obtained. m. p. [1 1 0—1 1 2 ° C]

Example 4

N— [1— (4-t—butyl-2-ethoxyethoxy) 1-3—hydroxypropyl] —2,6-difluorobenzamide 0.4 g, and catalytic amount of DBU in acetonitrile Then, 0.06 g of methyl isocyanate was added under ice-cooling and stirring, and reacted at room temperature. Two days later, the reaction solution was poured into ice water, extracted with ethyl acetate, washed with water, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The obtained crystals are washed with n-hexane and getyl ether and separated by filtration to obtain the desired N- [1— (4-t-butyl-2-ethoxyphenyl) 13- (N'-methylca Rubamoyloxy) propyl] —2,6-difluorobenzamide (Compound No. 42) 0.4 g was obtained. m. p. [1 0 9 — 1 1 1 ° C]

Example 5

N-[1-(4 _ t -butyl-2-ethoxyphenyl)-3-hydroxypropyl] 1,2,6-Dissolve 0.3 g of diflurobenzamide in 10 ml of dichloromethane, At room temperature, 0.16 g of trifluoroacetic anhydride was added and reacted at room temperature. The reaction solution is concentrated under reduced pressure, and the obtained crystals are washed and filtered with n-hexane and ethyl acetate to obtain the desired N— [1— (4—t—butyl—2—ethoxyphenyl) —3 — (Trifluoromethylacetoxy) propyl] 1,2,6 — 0.333 g of difluorobenzamide (Compound No. 44) was obtained. m.p. [133-135 ° C] Table 1 shows typical examples of the compound of the present invention including the above Examples.

Table 1

Table 1 (continued)

0 1

fZriO / S6df / XDd W800 / M6 OAV Table 1 (continued)

Z A R X n Ym Physical constant

MeS0 ₂₀ --CH2CH2-H 2-Br 2, 6- (0Me) ₂ *

Vis. 0i l

〃〃〃 2, 6-Me ₂ mp [114-116 ° C]

〃〃〃 4-'Bu 2.6-F2 mp [108-110 ° C]

C1- 〃〃〃〃 mp [135-138 ° C]

HO- 〃〃〃

C1- 〃〃 4-'Bu-2-0Et 〃 mp [114-115 ° C]

H0- 〃〃〃 mp mp [130-132 ° C]

MeS0 ₂ 0- 〃〃〃

MeNHC (= 0) 0- 〃〃〃 mp [109-111 ° C]

MeNHC (= S) 0- 〃〃〃〃 mp [57-59 ° C]

CF _{; t} C (= 0) 0- 〃〃〃 mp [133-135. C]

Table 1 (continued)

Table 1 (continued)

Table 1 (continued) No. Ζ A R X n Ym Physical Dragon

67 MeS0 ₂ 0--(¾2 112 112-H 2-CF ₃ 2.6-F2

68 〃〃 4-CF ₃ 〃 *

69 〃〃〃 2, 4-CI 2

70 〃〃 2, 6-Ch 〃

71 〃〃〃 2, 3-Ch 〃

72 〃〃〃 3, 4-Cb 〃

73 〃〃〃 2-C1.6.-F

74 〃〃〃 2-C1.4-F 〃

75 〃〃〃 2, 4-F2 〃

76 〃〃〃 2, 6-F2 〃

77 〃〃 2-F, 4- CI

Table 1 (continued)

Table 1 (continued) No. Ζ A R X n Ym Physical constant

89 MeS0 ₂ 0--(¾υΓΐϋ-H 2- CH-O'Pr 2, 6-F2

90 〃〃〃 3-Bt-2-0Et 〃

91 〃〃〃 3-Br-4-0Et

92 〃〃〃 4-Cl-2-0Et 〃

93 〃〃〃 2, 3-CI ₂ -〃

4-0 ⁿ Pr

94 〃〃 2, 4-Me ₂

95 〃〃〃 2, 3-Me _2-

4-OMe

96 〃〃 3, 4- (0Et) ₂ 〃

97 〃〃〃 4-0Et-3-'Bu 〃

98 〃〃〃 4-0 "Pr-3- 'Bu 〃

99 〃〃〃〃

Four-

Table 1 (continued)

8 I

WZlO / S6df / J «I ½800 6 OAV Table 1 (continued)

Table 1 (continued)

Number Z A R X n Ym Physical constant

133 CI- H 2-C1. 4-F 2, 6-F

134 2, 4-F ₂

135 2, 6-F ₂

136 2-F, 4-CI

137 3-Br, 4-Cl

138 2, 3, 4-Cl ₃

139 2, 3 5-Cl _{: i} , o, D ^_ r-,

141

142 4- ⁿ 0ct

143 4- ⁿ Dec Table 1 (continued)

SZI0 / s6fcvl3 «l_ν 娘 daughter

Table 1 (continued)

Table 1 (continued) ヮ

z A K Λ Π Y m

177 CI--CH2CH2-H 4 " ^l BuO- 2, 6-F2

178 〃〃 4-0 ₂ N- 〃

179 〃〃〃 4-H ₂ N- 〃

180 〃〃〃 4-Me ₂ N- 〃

181 〃〃 4-NC-U 〃

182 〃〃〃 4-MeS- 〃

183 MeS0 ₂ 0 undefined undefined 4-Me - 〃 inp [71-75 ⁰ C]

184 〃〃〃 4-MeS- amorphous

185 〃〃〃 mp mp [99-102 ° C]

186 〃 4-MeO- 〃 amorphous

*

3-C 1

187 MeS0 ₂ 0 -CH eCH -.- 〃

(cis) 4-OCH2-<T mp [99-101 ° C] Table 1 (continued) REM

Incense Z A R X n Ym Physical constant

2-C1

188 MeS0 ₂ 0 -CHMeCH ₂ -H 2, 6-F2 m [107-109 CJ

4 "0CH _2- ^)

(trans)

189 〃〃 2-C1 m [118-119 C]

(cis)

190 〃〃〃〃 mp mp [102-106 ° C]

(trans)

I9l 〃 -CH (CF _; JCH ₂ -〃 2-Br 〃 Vis. 0i l

*

192 〃 -CH2CH2- 〃 4-CF. 2- CI rap [81-87 ° C]

193 〃〃〃 2-Br 4-Br mp [114-116]

194 〃〃 mp [126-128 ° C]

19b `` 4-F m LlUb-lUo C J

196 〃〃〃 4-CN mp [125-127 ° C]

197 〃〃〃〃 4-CF, mp [127-129 ° C]

198 〃〃〃 2-SMe mp [lll-113t] Table 1 (continued)

C]

Table 1 (continued)

Table 1 (continued)

Table 1 (continued)

Table 1 (continued)

Z A R X n Ym Physical constant

243 HO-CH ₂ CH ₂ -H 2, 6-F ₂

Four- *

244 〃〃 2-C1-2-F 〃 *

245 〃〃〃〃氺

246 〃〃 3-Br-4-Cl 〃 *

247 〃〃 2, 3, 4-C1, 〃 *

248 〃〃〃〃 *

249 〃〃〃 *

250 *

F

251 〃〃〃〃

⁴ -'*

252 〃〃〃〃 *

253 〃〃〃 * Table 1 (continued)

Table 1 (continued)

Table 1 (continued) Compounds

畨 Z A R Xn Ym Physical constant

287 H0 -CHMeCH ₂ -H 2-Br 2, 6-F ₂ *

288 〃〃〃 *

289 〃〃〃〃 *

290 〃-CMe ₂ Cl-〃 2-Br 〃 *

291 〃〃〃 *

-CIIC11 _2- (trans)

292 〃〃 *

(cis)

293 〃 -CllMeCH ₂ -〃〃 2-C1 *

(trans;

294 〃〃〃 *

(cis)

295 〃〃〃〃 2.6-F2 *

(trans)

296 〃〃〃〃〃 *

(cis)

297 〃〃 4-'Bu 〃氺 Table 1 (continued) ^)

Z A R X n Ym Number of hooks

_{298 HO - CHMeCH 2 - H 4} -'Bu 2, 6-F 2

(trans)

299 MeS0 ₂ 0- 〃〃〃

(trans)

300 〃〃〃

(cis)

301 CI 〃〃〃

(trans)

302 〃〃〃〃

(cis)

303 MeS0 ₂ 0- -CH2CH,-〃〃 2-CI, 6-F

304 Cl 〃〃〃〃

305 HO 〃〃〃 2- CI

306 MeS0 ₂ 0- 〃〃〃

307 Cl 〃〃〃〃

308 HO 〃〃 2-C1.6.-F Table 1 (continued) 畨 ZARX n Ym

309 MeS0 ₂ 0--CH2CH2-H 4- tBu- 2-OEt 2- CI, 6-F

310 C1 〃〃〃

311 HO 〃〃 2-C1

312 MeS0 ₂ 0- 〃〃〃〃

313 Cl 〃〃

314 HO -CHMeCH ₂ -〃〃 2, 6-F2

(trans)

315 〃〃

(cis)

316 MeS0 ₂ 0- 〃〃〃

(trans)

317 〃〃〃〃

(cis)

318 CI 〃〃

(trans)

319 〃〃〃〃〃

(cis) Table 1 (continued) No.ZAR Xn Ym Physical basket

320 HO-CH2CH2-H 4-0 'Bu 2-C1.6-F

321 eS0 ₂ 0-

322 Cl

323 HO 2- CI

324 MeS0 ₂ 0-

325 Cl

_{326 HO -CHMeCH 2 - 2, 6} -F2

(trans)

327

(cis)

328 MeS0 ₂ 0-

(trans)

329

(cis)

330 CI

(trans) Table 1 (continued)

Table 1 (continued)

Table 1 (continued)

30 / Z1S6fcvlcw OAV

4 delivery

Table 2 (continued)

Compound NMR data: TMS (CDC1 _3, ppm)

184 2.34 Cm, 2H), 2.50 (s, 3H), 3.05 (s, 3H), 4.32 (m, 2H), 5.35 (m, 1H 6.58 (h 1) r1, r1l1, 11! R0 * Q3¾13 (^ _m 91] 1), 7 ί ·? ^ Fυ) -7.4 ¾fi UV Uli * SjHn

186 2.32 (m, 2H), 3.89 (s 3H 4.38 (t, 2H), 5.35 (q, IH), 6.70 (br.d, IH),

C D. QAU (v _m lll,

189 1.59 (d, 3H 2.32 (m, 2H), 3.00 (s, 3H), 4.90 (m, IH), 5.58 (m, IH),

1 S) D.7 / 7 / fDT.0 I 1n u \ ;, P D..yλ (vt, Δ QϊUι), _t 7 I.Z 9 (

丄 1 _7 /.4 Α Ί / νΐ _m ϊΐ, On

190 1.52 (d, 3H), 2.28 (m, 2H 3.10 (s, 3H), 4.94 (m, IH), 5.T0 (m, IH),

(.t rans) b.ootur.d, 1H), b.9, H, 7. \-(.bulm, 5H)

191 2.41 (m, 1H), 2.72 (m, 1H), 3.15 (s 3H), 5.09 (m IH), 5, 67 (in, IH), 691 (m, 3H), 7.12-7.6 `` 5 (/ m, 5 `` H ヽ)

192 2.35 (m, 2H), 3.02 (s, 3H), 4 · 33 (m, 2H), 5 · 44 (m, 1H 6 · 82 (br.d 1H 7.27-7.70 Cm, 8H)

193 2.47 (m, 2H), 3.02 (s, 3H), 4.33 (m, 2H 5.63 (m, IH), 7.00 (d to b, IH), 7.12-7.72 (m, 8H)

194 2.48 (m, 2H), 3.05 (s 3H), 4.34 (m, 2H), 5.63 (ra, IH), 7.02 (br.d, IH), 7.15-7.93 (m, / H)

198 2.45 (s m, 6H), 3 05 (s 3H), 4.39 (m 2H) .5.69 (m, IH), 7.03-7 63 (m, 9H

,

199 2.45 (m, 2H), 2.51 (s, 3H), 3-02 (s 3H), 4 32 (m, 2H), 564 (nt, 1H), 7.00 (

Dr. d, 1 π J, I 丄 /. / O ^ m, on)

200 2.48 (m 2H), 3.03 (s 3H), 4.32 (m, 2H), 5.68 (m, IH), 7.00 (br.d, IH),

7 99-7 Q Tm QH

201 2.41 (s, 3H), 2.47 (m 2H), 3.03 (s, 3H), 4.35 (m, 2H), 5.65 (ra, IH),

nr 1 u ^ 7 1 _7 7

VD Γ. A in, /. 丄 ^ t I ( _m

0.ϋ m, on)

202 2.44 (m 2H), 3.00 (s, 3H), 4.30 (m, 2H 5 · 38 (m 1H), 6.59 (br.d IH),

ί 0 ί ί

205 1.41 (t, 3Η), 2 37 (m 2H 3.03 (s, 3H), 4.03 (q, 2H), 4.30 (m, 2H),

5.36 (m, 1H), 6.20 (br.d, IH)

206 2.41 (m, 2H 2.43 (s, 3H), 3.04 (s, 3H), 4.32 (m, 2H), 5.50 (m, IH),

6 72 (br.d, IH), 6.96 (t, 2H) .7.28-7.60 (m 8H)

207 2.42 (m, 2H 3.06 (s, 3H), 4.36 (m, 2H), 5.49 (m, IH), 6.42 (br.d IH), 6.95 (t, 2H), 7.28-7.78 (m, 9H)

Table 2 (continued)

Compound NMR data: TMS (CDC1 _3, ppm)

Number

1 q ^ dn IH) 2 2 (m 1 H) 2 60 (br IH) 3 73 (m 2H) 5 50 (m IH)

6 · 95 (t, 2H), 7.13 (br.d, 1H), 7.27-7.67 (m, 5H)

1 q7 (m IH 2 2B (m 1 H) 2 72 (hr 1 H) 3 77 (m 2H) 53 3 (m 1 H),

6 93 (br.d, IH), 7 03 (m, IH), 7 18-7.68 (m, 5H)

? 97 0 88 (m lu »(Jil 1 22-1 O (m 8 (JHli) 17 (, m 2H) 1 Q (, m IH) 2 21 Cm, IH)

3.78 (m.2H), 3.94 (t, 2H), 5.41 (m, IH), 6.42 (br.1H) .6.83-7.OOdn, 4H), 7.25-7.45 (m, 3H)

228 0.94 (t.3H), 1.63 (m, 2H), 1.95 (m.IH), 2.22 (m, IH), 2.56 (m, 2H), 3.78 (

IUi 乙 Π 3.m, 丄 Π ノ, D. Do \ ul .Q, Π Π ノ .0, α4 v I, άη) * i · 丄 J /. ^ VIII * On;

229 2.00 (m, IH), 2.15 (m, 1H), 2.75 (br., IH), 3.82 (m, 2H), 5.76 (m, 1H), 6.9, t, 丄 11, iU Dr., ， OL (/ ΠΙ, On

230 2.08 (m, 2H), 2.77 (br., IH), 3.73 (m, 3H), 5.67 (m, 1H), 6.92 (t, 2H),

7 ΟΛ

/.ν 7 Cm ヽ

D (.ni, on;

231 2.10 (m, 2H), 3.73 (m, 2H), 5.60 (m.1H), 6.87-7.45 (ra, 8H)

232 2.12 (m, 2H), 2.54 (br.t, IH), 3.77 (m.2H), 5.72 (m, 1H),

6.88-7.50 (ID.7H)

233 2.10 (m, 2H), 2.98 (br., IH), 3.78 (m, 2H), 5.95 (m, IH),

6.78-7.02 (m, 5H), 7.18-7.45 (m, 2H)

234 2.10 (m.2H), 2.85 (m, IH), 3.82 (ra, 2H), 5.95 (m, IH), 6.65 (br.d, 1H), 6.88-7.08 (m, 3H), 7.09-7.39 (ra, 3H)

235 1.96 (m.lH), 2.22 (m, IH), 2.80 (br., LH), 3.88 (m, 2H), 5.43 (m, IH)

OO U U · ΙΠ ノ D, 0¾ JU Km, 丄 ώΠ ノ

236 1.93 (m, 1H), 2.20 (m, IH), 3.76 (m, 2H), 5.42 (m, IH), 6.82 (br.d, IH), fi U-QQ (, t し)ノ 7 i.9 LΠ-7 I. DO C Vimlli JHfl ^ ノ

237 1.46 (t, 3H), 2.07 (m, 2H), 3.74 (m, 2H), 4.08 (m, 2H), 5.50 (m, IH),

6.82-7.03 (ra, 5H), 7.18-7.47 (m, 2H)

238 1.93 (m, 1H), 2.22 (m, IH), 3.77 (m, 2H), 5.41 (m.IH), 6.88-7.50 (m, 7H)

239 1.92 (m, IH), 2.17 (m, 1H), 2.82 (br., 1H), 3.75 (m.2H), 3.88 (s.3H), 535 (m IH) 6 88 (br IH) 6 94-6 99 (m H) 7 22-7 7 (m 3H)

240 1.09 (t, 3H), 1.39 (s, 9H), 1.77-2.05 (m, 3H), 2.25 (m, IH),

2.45 (br., 1H), 3.77 (ra, 2H), 3.95 (t, 2H), 5.40 (ra, IH), 6, 35 (br. D, 1H),

6.81-7.01 (in, 3H), 7.11-7.44 (m, 3H)

241 1.38 (s, 9H), 1.45 (t, 3H), 1.94 (m, 1H), 2.22 (m, IH), 3.05 (br., IH), 3.88 (m, 2H), 4.04 (q, 2H) , 5.40 (m, 2H), 6.35 (br.d, IH), 6.80-7.00 (m, 3H), 7.12-7.48 (m, 3H) Table 2 (continued)

Compound NMR data: TMS (CDC1 _3, ppm)

Turn

242 1.95 (m, IH), 2.10- (m, IH), 2.58 (m, IH), 3.67 (m, 2H), 3.78 (s, 3H), 5.52 (m, IH), 6.65-7.57 (m, 6H 8.80 (br.d, IH)

243 2.00 (m, IH), 2.25 (m, IH), 3.08 (br.IH), 3.82 (m, 2H), 5.48 (m, IH), 6.74 (br.d, IH) .6.94 (t, 2H ), 7.28-7.64 (m, 10H)

244 2.08 (m, 2H), 3.72 (ra, 2H), 5.58 (m, 1H 6.94 (t, 2H), 7.02-7.43 (m, 5H) 1 <J107 (t 3H) 1 88 (m 3H) 2 13 (m IH) 2 43 (br IH) 377 (m 2H)

3.99 (m, 2H 5.69 (m, 1H 6 ・ 80-7 ・ 00 (m 3H), 7.07 (br.d IH), 7.25-7.48 (ra, 2H)

^ O 11 · Q i? OV / Clmll 1 U Π), 9 17 ff Vm HI * IH Π, 9 ，, J \ (Vh Ur I. 1 Π, 37 ί? 乙 (,, 9 Otsu W Π) ノ, ^ >> J, ^ OfiU imIII »IH Π) ノ,

6.92 (t, 2H 7.16 (br.d, 1H), 7.18-7.66 (m 4H)

9 Q «I'm C QO (

4/17 丄丄 1. OO VIU, 丄 1 Π ノ, 9 1 ς OU \ C CO

L. 丄 0 ( _m IU, 丄 1]

Π Roh, Q 717 I Cmil * ώΠ _{Roh, O, D Ο V m 111} t 1丄Π Roh, ϋ · ΌΔ l _t Roh,

7.26-7.47 (m, 3Η), 7.56 (br.d, IH)

On. On), 丄. Yo in, 丄 n, ά, άnt, 丄 n, 乙. Oy vu » (br.d, IH), 6.93 (t, 2H),

7 00_7 fif m QH ^

249 2.00 (m 1H 2.22 (m, IH), 2.33 (br.IH), 3.75 (m.2H 5

34. 34 L, 乙 Π,. OU f, OU V ll, ίίΠ, J. i 3 U U, 丄 Π

250 2.02 (m, 1H), 2.20 (m, 1H 236 (s 3H), 2.60 (br.1H 3.74 (m, 2H)

c ϋ. ¾ HI HI, 1 丄

R Ό9ύ Q ΐίHΠno, 9 O., 1 丄 0 U Ch UrI * 11Πno

251 1.96 (m, 1H2.22 (ra, 1H3.75 (ra 2H), 5.45 (m, IH), 6.80-7.58 (m, 12H)

1, ¾ D k i>) till, 乙. \ J \ J Klti Π, L. 111 * Π,.? U I., 丄 Π, O U 111, ώΠ,

5.50 (m 1H 6.72 (br.d, 1H 6 ・ 95 (t, 2H 7 ・ 28-7 ・ 62 (m, 9H)

L o I \, il)

6.78 (br.d, 1H 6.95 (t 2H 728-7.57 (m, 8H)

0Q C74 ¾

H) 2 B2 (t 2H) 262 (br IH)

3.79 (m.2H), 5.73 (m, IH), 6.92 (t, 2H 7.15 (br.d, IH),

7.20-7.62 (m, 8H)

255 2.02 (m, lH), 2.28 (ra, IH), 2.80 (br., IH), 3.81 (ra, 2H), 5.55 (m, 1H

6.82 (br.d, IH), 6.95 (t, 2H), 7.22-7.63 (ra, 8H)

256 2.05 (m, 2H), 3.35 (br., IH), 3.62 (m, 2H), 5.30 (m, 1H 6.87 (t, 2H), 7.21-7.56 (m, 9H), 8.58 (br.d, IH)

257 2.09 (m, 2H 2.60 (br.IH), 3.69 (m, 2H), 5.40 (m, IH), 6.94 (t, 2H), 7.32-7.66 (m, 8H), 8.55 (br.d, IH )

258 1.91 (ra, IH), 2.15 (ra, IH), 2.75 (br., IH), 3.73 (ra, IH), 3.88 (s, 3H), 5.35 (m, IH), 6.80 (br.d, IH), 6.93 (t, 2H), 7.20-7.42 (m, 4H) Table 2 (continued)

Compound NMR data: TMS (CDC1 _3, ppm)

259 1.99 (m, IH), 2.25 (m, IH), 2.58 (br., IH), 3.79 (m, 2H), 5.50 (m, IH), 6.82-7.00 (m.3H), 7.22-7.62 ( m, 8H)

fiO 200 (m 2H) 2 40 3H) 3 09 (br IH) 3 73 (m 2H) 5 52 (m IH)

6.73 (br.d, IH), 6.92 (t 2H), 7, 16-7.42 (m, 4H)

261 1.98 (in, 1H), 2.22 (ra, IH), 2 52 (br, 1H 3 78 (ra 2H), 5.52 (m, IH), L

262 1.29 (d, 6H), 1, 98 (ra, 1H227 Cm.1H 2.96 (m, 1H 3.42 (br.IH),

U, D Π, D · Π3 J \ L,,

7.24- 7.60 (m, 9H)

OO 丄.! D a, Dn »L, UU ni, in, ΔΌ 丄 H ri, 乙. Ϋ́ϋ ^ D Γ., 丄 ,, ΰ 丄, III,))»

4.59 (m, IH), 5.49 (ra, IH), 6.65 (br.d IH), 6.89-7.00 (m, 4H), 7.28-7.60 (m, 7H)

264 1.91 (m, IH), 2.15 (ra, IH), 2.95 (br., IH), 3.72 (m, 2H), 5.35 (m, IH), 6.97 (br.d, IH), 7.20-7.68 ( ra, 8H)

265 1.98 (m, IH), 2.25 (ra, IH), 3.80 (m, 2H 5.20 (s, 2H), 5.48 IH),

6.80 (br.d, lH), 6.88-7.60 (m, 16H)

266 2.08 (ra, 2H), 2.59 (s, 6H), 3.72 (m, 2H), 4.05 (m.IH), 5.80 (m, IH),

7.02-8.22 (m.8H), 10.63 (br.d, IH)

267 1.94 (m, IH), 2.18 (m, IH), 2.75 (br., IH), 3.75 (m, 2H), 3.90 (s, 3H), 5.44 (m, IH), 6.70 (br.d, IH), 6.94 (t, 2H), 7.21-7.44 (ra, 5H)

268 1.90 (br., IH), 2.05 (m, 1H), 2.26 (m, IH), 3.85 (m.2H), 5.IKm, IH).

6.85 (br.d, IH), 6.40-7.62 (m, 7H)

269 2.03 (m, IH), 2.29 (m, IH), 3.83 (m, 2H), 5.52 (m, IH), 6.83 (br.d.IH), 6.95 (t, 2H), 7.30-7.73 (m , 9H)

270 2.03 (m, 1H), 2.28 (m, IH), 2.85 (b, IH), 3.78 (m, 2H), 5.52 (m, IH), 6.92 (br.d, IH), 6.96 (t, 2H), 7.21-7.89 (m, 8H)

271 2.15 (ra, 2H), 3.05 (br., IH), 3.85 (m, 2H), 5.70 (m, 1H 6.65 (br.d, IH), 7.05-7.90 (m, 8H)

272 2.15 (m, 2H), 2.94 (br., IH), 3.75 (m, 2H), 5.63 (ra, 1H

7.10-7.80 (m, 9H)

273 2.15 (m, 2H), 3.15 (br., IH), 3.82 (m 2H), 5.65 (m IH),

7.10-8.07 (ni, 9H)

274 2.10 (m, 2H), 2.80 (br., IH), 3.75 (m, 2H), 5.04 (s.2H), 5.68 (ra, IH), 6.82-7.06 (m, 5H), 7.28-7.48 ( ra.7H) Ns / 6dr /: S £ OAV L6

Table 2 (continued)

Compound NMR data—: TMSCCDCli, p m)

Number

292 2 2T (ra.2H) 2 39 (br IH), 4 90 (m, IH), 5 55 (m, IH), 6 93 (t.2H)

7.06-7.69 (ra, 11H)

293 1 25 (d 3H) 1 94 (m 2H) 3 29 (d, IH), 3 95 (m, IH) .5 45 (m IH)

7.03 (br.d, IH), 7.23-7.72 (m, 8H)

294 1 25 (d 3H) 1 80 (d IH) 1 97 (m 2H) 3 89 (m IH) 5 21 (m IH)

6.98 (br.d, IH), 7.28-7.67 (m, 8H)

295 1 24 (d 3H) 1 92 (ra 2H) 2 92 (d IH). 3 92 (in, IH) 5 45 (m IH)

6.95 (t 2H), 6.98 (br.d, IH), 7.22-7.53 (m, 5H)

296 1.24 (d, 3H 1.82 (d, IH), 1.98 (m, 2H), 3.92 (m, 1H 5.20 (m, IH),

6.95-6.97 (m, 3H), 7.22-7.52 (m, 5H)

297 1.25 (d, 3H), 1.31 (s, 9H), 2.02 (m, 2H), 3.92 (m, IH), 5.27 (m, IH),

6.65 (br.d, IH), 6.92 (t, 2H), 7.27-7.43 (m, 5H) The compound of the present invention is useful for controlling agricultural pests, sanitary pests, storage pests, clothing pests, house pests, etc. The following can be used as typical examples.

Lepidopteran pests, for example, Hasmonyoto, Totoga, Tamanayaga, Aomushi, Yumanaginba, Konaga, Chinokokamamonaki, Chiyamahamaki, Momomosinkiga, Nashihime Shinki, Mikanhamagamoga, Chiyamahogamoga , Nikameiga, Kobunomeiga, Kokuchi Biankombora Amelie Kashiro Hitori, Sujimadarameiga, Heliotis, Heli Koverpa, Aggrotis, Iga, Kodoringa, Peta Hemiptera pests, such as potato beetles, for example, peach aphid, peach aphid, Nisedai koa aphid, oak bilge aphid, hosohelikamushi beetle, okakusamemushi beetle, fork beetle, beetle beetle, onoshi konara Tapa's whiteflies, pear whiteflies, pear beetles, brown beetles, brown beetle, slime beetle, sage low birch, black beetle, etc. Rice water beetle, black beetle, azuki beetle, beetle beetle, brown beetle, diablo genus, tobacco beetle, flat beetle bark beetle, matsunomadara mikiri, sesame beetle mikiri, agliothus Diptera insect pests such as cormorants, cockroaches, and locust beetles, for example, Dermatophagous fly, Perimipa, Mikankomipa, Tanepa'e, Rice hamogrippa ', Kiroshoujijiyoubae, Sashibae, Koga sunset, Anetai Shima, Shinano, Madara, etc. Hymenoptera pests, such as Thrips palmi Karny, Chrysanthemum thisrane, Hymenoptera pests, such as Diplomatica, Diplomatidae, Kabrahabachi, etc., Orthoptera pests, such as the German cockroach, Blattella germanica , Pterodactyla, etc., Isoptera pests, for example, House termites, Sphagnum termites, etc., Leptopteran pests, for example, human fleas, Lice pests, for example, human lice, mites, for example, Na Mihadani, Kanzahadani, Mikanhadani, Lingo spider mite, Mikansabida ni, Lingosavida ni, Chi Plant-parasitic nematodes, such as P. serrata, Blebipalpas, G. tetranicus, Robin's mite, P. aeruginosa, Dermatophagoides farinae, Dermatophagoides farinae, Dermatophagoides farinae, etc. Yu, soybean soy centiyu, rice singare centiyu, pine nosy centiyu and so on.

In addition, in recent years, many insect pests such as moth moth, pinworm, leafhopper and aphid have developed resistance to organic phosphorus agents and carbamates, which has led to a problem of insufficient efficacy of these agents. Also effective drugs are desired. The compound of the present invention is an agent having an excellent insecticidal effect not only on susceptible strains but also on insect pests of organic phosphorus, carbamate and pyrethroid-resistant strains.

The pesticidal composition of the present invention contains a compound represented by the general formula [I] as an active ingredient, and can be used as a pure active ingredient compound. It is used in the form to be obtained, that is, wettable powder, water solvent, powder, emulsion, granule, flowable and the like. As an additive and a carrier, when a solid agent is used, vegetable powder such as soybean flour and flour, diatomaceous earth, apatite, gypsum, talc, bentonite, clay, and other mineral powders Organic and inorganic compounds such as sodium benzoate, urea, and sodium sulfate are used.

For liquid dosage forms, vegetable oils, mineral oils, petroleum fractions such as kerosene, xylene and sorbent naphtha, cyclohexane, cyclohexanone, dimethylformamide, dimethylsulfoxide, Use trichloroethylene, methylisobutyl ketone, water, etc. as the solvent. In these formulations, a uniform and stable Surfactants can be added if necessary to take the form. The wettable powder, emulsion, aqueous solvent, and flowable thus obtained are diluted to a predetermined concentration with water to form a suspension or emulsion, and the powder and granules are sprayed or applied to plants as they are. Used in soil and nutrient solutions.

It goes without saying that the compound of the present invention alone is sufficiently effective, but it can also be used in combination with various insecticides, acaricides, nematicides, fungicides and synergists.

Representative examples of insecticides and acaricides that can be used by mixing with the compound of the present invention are shown below.

Organophosphorus and carbamate insecticides:

Phenthion, Phenyltrothion, Diazinone, Chlorpyrifos, ESP, Bamidothion, Phentoate, Dimethoate, Formothion, Marathon, Trichlorfon, Thiomethon, Phosmet, Dichlorvos, Asefulfone , EPBP, methyl parathion, oxydimethonmethyl, ethion, salicion, cyanophos, isoxathion, pyridafenthion, hosalon, methidathion, sulprophos, chlorphenvinphos, tetrachlorphobins, dimetylphobinphos Sofinphos, ethylthiomethone, propinophos, pyraclophos, monochlorophos, azinphosmethyl, aldicarb, mesomil, thiodicarb, carbofuran, carbosulfan, be Furakarubu, Furachiokarupu, Provo sake, B P M C, M T M C, M I P C, force Rubari Le, pyrimidone curve, Echiofu E Nkarupu, Hue Nokishikarupu etc.

Pyrethroid insecticides:

Permethrin, cypermethrin, deltamethrin, fenvalerate, fenproprin, pyrethrin, arelesline, tetramethrin, resmethrin, remetrin Lin, Prono, ⁰ Screen, Phenotrin, Protoline, Fully Parinate, Siflutrin, Cyhalothrin, Phenolecitrine, Etfenprox, Cycloprotoline , Trolamethrin, sirafluorfen, brofenprox, akrinatrin, etc. Benzoyl Rare Other Insecticides:

Difluvenzuron, chlorfluazuron, hexaflumuron, triflumuron, tefluvenzuron, flufenoxuron, flucycloxuron, buprofezin, pyriproxyfen, methoprene, benzepin, jafenthiuron, imidacloprid, fipronil , Nicotine sulfate, rotenone, cartap, thiocyclam, bensultap, metaaldehyde, machine oil, microbial pesticides such as BT and entomopathogenic viruses.

Nematicide:

Phenamiphos, phosthiazate, etc.

Acaricide:

Chlorbenzilate, phenylisobromolate, dicophor, amitraz, BPPS, benzomate, hexithiaox, fenbutatin oxide, polynactin, quinomethionate, CPCBS, tetrazion, avermectin, mil Bemectin, clofentidine, sihexatin, pyrigben, phenpyroximate, tebufenvirad, pyrimidifene, phenothiocalp, dienochlor and the like.

Fungicide :

Thiophanate methyl, benomyl, carbendazole, thiabendazol, floretto, thiuram, ziram, zineb, maneb, polycarbamate, IBP, EDDP, fusaride, probenazole, Isoprothiolane, TPN, captan, polioxin, blasticidin S, kasugamycin, strebtomycin, paridadamycin, tricyclazole, pyrokirone, phenazine oxide, mepronil, Flutolanil, Pencyclone, Iprodione, Himexazole, Metaaxil, Triflumizole, Trifolin, Triazimefon, Vitertanol, Fuenalimole, Propiconazole, Simoxanil, Prochloraz, Difurazoate, Hexaconazo Mikuro, Yunil Jikurome Jin, Tech port Futaramu, pro Pinebu, dithia Roh emissions, fosetyl, Binkurozori down, Puroshi Mi Dong, Okisajikishi Le, Guazachin, Puropamokarupu hydrochloride, fluazinam, Okiso Rini' click acid, arsenate Dorokishii Sokisazo Ichiru.

Next, examples of preparations will be described. The carriers to be added, surfactants, etc. It is not limited.

Example 6 Emulsion

Compound of the present invention 10 parts

Alkyl phenyl polyoxyethylene 5 parts

Dimethylformamide 50 parts

Xylene 3 5 parts

Mix and dissolve the above, dilute with water before use and spray as an emulsion.

Example 7 wettable powder

Compound of the present invention 10 parts

Higher alcohol sulfate 5 parts

Diatomaceous earth 80 parts

5 parts

Mix the above, pulverize into fine powder, dilute with water before use and spray as a suspension Example 8

5 parts of the compound of the present invention

Talc 9 4.7 parts

0.3 series

Mix and grind the above and spray as it is when using.

Example 9 granules

5 parts of the compound of the present invention

Cray 7 3 copies

Bentonite 20

Dioctylsulfosac cinnamate sodium salt 1 copy

1 part of sodium phosphate

Granulate the above and apply as it is when used. Industrial applicability:

Test Example 1 Efficacy against Aphids

10 days after germination, seedlings sown in three-size bowls were inoculated with adult Aphid aphids. One day later, the adults were removed, and the nymphs, which were born by the nymphs, were diluted with water to a compound concentration of 125 ppm according to the emulsion formulation shown in Example 6 of the drug. Sprayed drug solution was sprayed. They were placed in a constant temperature room at a temperature of 25 ° C and a humidity of 65%, and the insecticidal rate was examined 6 days later. The results are shown in Table 3.

Table 3 Insecticidal rate 6 days after compound number (%)

Two

7

Two

Three

Five

Four

Five

6

Two

5 0 0

9 0 0

0 0 0

Control compound A 6

Control compound B 100

Control compound A Control compound B

(Pirimi curve) (Tiomethone) Test Example 2 Efficacy on atropia

According to the formulation of the wettable powder shown in Example 7 of the drug, the compound was diluted with water so that the compound concentration was 125 ppm. Corn leaves were immersed in the chemical solution for 30 seconds, air-dried, and then put into a petri dish containing five third-instar larvae. Cover with glass lid and temperature 25. C, placed in a constant temperature room with a humidity of 65%, and examined the insecticidal rate after 5 days. The results are shown in Table 4.

Table 4 Insecticidal rate after saying Compound No. 5 (%)

5 5 1 0 0

1 1 9 1 0 0

1 2 0 1 0 0

Control compound C 40 Control compound C

(Chlordimeform)

Test Example 3 Efficacy against Namihadaji

After inoculating 17 adult females of organic phosphoric acid-resistant Naminipada on the first true leaf 7-10 days after germination of green sowing seeds in 2-inch pots, According to the wettable powder formulation shown in Fig. 7, a chemical solution diluted with water was sprayed so that the compound concentration would be 125 ppm. Place in a constant temperature room at a temperature of 25 ° C and a humidity of 65%, remove the adults 3 days after spraying, and determine whether the eggs laid during these 3 days have grown to adults.

On the 1st day, they were surveyed to determine the effectiveness of miticides. The results are shown in Table 5. The acaricidal effectiveness was determined by the following formula. Non-treated adult-Number of treated adult

Acaricidal effectiveness (%) = X 1 0 0

Number of untreated adults Table 5 Compound number Acaricidal effectiveness (%)

9 7

9 9

9 5

9 9

5 5 9 9

1 9 0 0

2 0 0 0 Control compound C 5 5

Claims

The scope of the claims

1. Formula [I]

[Wherein, X is hydrogen, halogen, (halogen or a phenyl group which may be substituted)

An alkyl group which may be substituted with a phenyl group, an alkoxy group which may be substituted with a halogen or a phenyl group which may be substituted, a phenyl group which may be substituted, and a phenyl group which may be substituted.ノ Nonoxy group, optionally substituted alkylthio group, optionally substituted phenylthio group, nitro group, optionally substituted amino group, cyano group, alkylsulfonyloxy group, optionally substituted pyridyloxy group Represents a group or an optionally substituted phenylsulfinyl group.

n represents an integer of 1 to 5, and when 2 or more, X may be different.

Y represents halogen, cyano, an optionally substituted alkyl group, an optionally substituted alkoxy group, an alkylthio group, an optionally substituted amino group or a nitro group. m represents an integer of 1 to 5, and when it is 2 or more, Y may be different.

Z is a hydroxyl group, a halogen, an optionally substituted alkylsulfonyloxy group, an optionally substituted phenylsulfonyloxy group, an optionally substituted acetateoxy group, an optionally substituted benzoyloxy group, An optionally substituted alkoxycarboxy group, an optionally substituted rubamoyloxy group, an optionally substituted thiocarbamoyloxy group, an optionally substituted sulfamoyloxy group, or an optionally substituted phosphonyloxy group Represents a group.

A represents an optionally substituted ethylene.

R represents hydrogen or a benzoyl group which may be substituted. ] The amide compound represented by these.

2. X is hydrogen, halogen, (halogen also is properly (halogen, alkyl, C haloalkyl also properly in C Bok "alkoxy) may be substituted with an optionally substituted Fuweniru group} C, ₂ alkyl group, Les , Logen or (halogen or A phenyl group which may be substituted with a C alkyl group, a C ₁₂ alkoxy group which may be substituted with a ί group, a {halogen, Ηalkyl, ϋ alkoxy, ₆ haloalkyl, aralkyloxy group, a phenyl group which may be substituted A phenoxy group optionally substituted with Cl-β alkyl or C ^ B alkoxy, a C, -e alkylthio group, a phenylthio group optionally substituted with halogen, a nitro group,

{C, -G alkyl or mono} optionally substituted amino group, cyano group, C! -6 alkylsulfonyloxy group, レ, logen, C1-6 alkyl, C1-6 Represents a pyridyloxy group which may be substituted with haloalkyl, a phenylsulfinyl group which may be substituted with {C ^ fi alkyl, 0, -6 haloalkyl}, and n represents an integer of 1 to 5, When X is 2 or more, X may be different, Y is halogen, cyano, C,-(! Alkyl group; haloalkyl group, <; alkoxy group, "alkylthio group, alkyl or mono-substituted by alkyl} M represents an integer of 1 to 5; when m is an integer of 2 or more, Y may be different; and Z is substituted with a hydroxyl group, a halogen, a halogen, a halogen or a halogen. which may be C, - "Arukirusu Rufoniruokishi group, with _β alkyl} An optionally substituted phenylsulfonyloxy group, a (Cn-acetoxy group optionally substituted with a halogen), a benzoyloxy group optionally substituted with a} or a halogen, an optionally substituted C ,; A carbamoyloxy group, which may be mono- or di-substituted with a C カルボニル -alkyl, phenyl or halophenyl, a thiocarbamoyl which may be substituted with a C n-alkyl or phenyl; An alkoxy group,,; a sulfamoyloxy group which may be substituted with alkyl or di} or a phosphonyloxy group which may be substituted with {C, -fi alkyl}; (Di ,; alkyl, C haloalkyl or phenyl) represents ethylene which may be substituted by R, and R is hydrogen or benzoyl which may be substituted by , Claim 1 § Mi de compound according.

3. X is hydrogen, halogen, or phenyl which may be substituted with halogen or halogen (C alkyl, C, -G haloalkyl or C _1; alkoxy) phenyl which may be substituted. ₍₂₎ an alkyl group, a phenyl group which may be substituted with an alkyl group, a halogen or a C.- ,;

- Five Alkoxy group, (halogen, alkyl, C i-alkoxy or C (i-alkyl group optionally substituted by phenyl group), phenyl, logen, c, _-c alkyl or alkoxy group A phenyloxy group, a _6- alkylthio group, a phenylthio group optionally substituted with {halogen}, a pyridyloxy group, a nitrogen group optionally substituted with

{C-alkyl or mono or di} represents an amino group or a cyano group which may be substituted, n represents an integer of 1 to 5, when 2 or more, X may be different, and Y is halo gen, C, - ₆ alkyl or ds alkoxy group, m represents an integer from 1 to 5, when two or more Y may be different from each, Z is hydroxyl, halogen, les, in Rogge emissions} Optionally substituted C ₆ alkylsulfonyloxy group, {C i- ₆ alkyl} optionally substituted phenylsulfonyloxy group, (halogen) optionally substituted C!-<Sub>ethoxy> group A benzoyloxy group which may be substituted with (halogen), a C, -alkoxycarbonyloxy group, a mono- or di-substituted rubamoyloxy group which may be substituted with {C n alkyl, phenyl, halofenyl, With alkyl or phenyl} Conversion which may be Chio carbamoyl O alkoxy group, {C; alkyl mono Moshiku di} sul optionally substituted sulfamoyl O alkoxy group, or {C, - at _fi alkyl} optionally substituted off Osufu Oniruokishi The amide according to claim 1, wherein A represents ethylene optionally substituted by {C alkyl or phenyl}, and R is hydrogen or a benzoyl group optionally substituted by {halogen}. Compound.

4. A is-Cl- aCHa-

3. The amide compound according to claim 2, wherein in the formula, r ¹ and r ² are the same or different and each represents hydrogen, C κ alkyl, or _(i represents haloalkyl or phenyl).

5. A is -Ct ^^ CHa-

4. The amide compound according to claim 3, wherein, in the formula, r ³ and r ′ ¹ are the same or different and each represents hydrogen, C,-(; alkyl or phenyl).

6. The expression [in

NH (II)

H 0-A

[Wherein, A, n and X represent the same meaning as described above. A compound represented by the formula (III):

Ym (III)

[In the formula, W represents a leaving group, and n and Y represent the same meaning as described above. [I ′] characterized by reacting a compound represented by the formula

HO-A 0

[Wherein, A, m, n, X and Y represent the same meaning as described above. ] The manufacturing method of the compound represented by these.

7. Formula [I] according to claim 1, 2, 3, 4 or 5

[Wherein, A, m, n, X, Y and Z represent the same meaning as described above. ] An insecticide and acaricide, characterized by containing one or more of the compounds represented by the formula (1) as an active ingredient.