WO2001000568A1

WO2001000568A1 - Hydrazone derivatives and pest controllers

Info

Publication number: WO2001000568A1
Application number: PCT/JP2000/004232
Authority: WO
Inventors: Kazumi Yamamoto; Kazuhiko Oyama; Takeshi Teraoka
Original assignee: Meiji Seika Kaisha, Ltd.
Priority date: 1999-06-28
Filing date: 2000-06-28
Publication date: 2001-01-04
Also published as: AU5704000A; JP4712261B2

Abstract

Compounds of general formula (I) and salts and solvates of the same. In said formula, R?1, R2, R3, R4 and R5¿ are each hydrogen, halogeno, optionally substituted alkyl, or optionally substituted phenyl, provided that all of R?1, R2, R3, R4 and R5¿ do not represent hydrogen; R6 is optionally substituted phenyl or an optionally substituted five- or six-membered saturated or unsaturated heterocyclic group; and R7 is hydrogen, optionally substituted alkyl, optionally substituted alkoxycarbonyl, optionally substituted alkanoyl, or -CO-NR11R12 (wherein R?11 and R12¿ are each optionally substituted alkyl or optionally substituted alkoxy).

Description

Description Hydrazone derivatives and pesticides Background of the invention

Field of the invention

The present invention relates to a novel hydrazone derivative and a pesticidal agent containing the same as an active ingredient.

Related technology

Many active substances have been found to have an effect of controlling various agricultural pests, sanitary pests, and plant diseases, and pesticides containing them as active ingredients have been developed. Japanese Patent Application Laid-Open No. 9-143032 discloses a compound having a cycloalkyl group, and includes agricultural pests, sanitary pests, grain storage pests, clothing pests, house pests, and various plant pathogens. It shows that it shows an effective control effect on pests. However, no report has been made on a hydrazone derivative having a substituted cyclopropyl group and its pesticidal activity.

Summary of the Invention

An object of the present invention is to provide a compound having excellent pest control activity and a pest control agent.

The compounds according to the invention are compounds of the formula (I) and salts and solvates thereof.

(In the above formula,

R 'RR ^3, R and R ^5, which may be the same or different

A hydrogen atom;

A halogen atom;

Ci-4 alkyl optionally substituted by a halogen atom; or a phenyl optionally substituted by d-4 alkyl or d-4 alkoxy (the alkyl and the alkyl moiety may be substituted by a halogen atom),

However, R ¹ RR ³ , R and: ⁵ do not all represent a hydrogen atom, and R ⁶ is

Phenyl (this phenyl is a halogen atom; d- ₄ alkyl optionally substituted by a halogen atom; C ぃ₄ alkoxy optionally substituted by a halogen atom; cyano; nitro; amino; one S (= 0) nR ¹³ (n represents 0, 1, or 2; R ¹³ represents d- ₄ alkyl optionally substituted by a halogen atom); -OQ-Ph (Q is a bond or substituted by a halogen atom substituted by one or more substituents selected from and Penjiru optionally substituted by a halogen atom; - also good C, ₄ alkylene, P h is a halogen atom represent an optionally phenyl substituted by) ); Or

5- or 6-membered saturated or unsaturated heterocyclic group (the heterocyclic group is a halogen atom; an alkyl optionally substituted by a halogen atom; a d- ₄ alkoxy optionally substituted by a halogen atom) Cano; Nitro; Amino; 1 S (= 0) nR ¹³ (n represents 0, 1, or 2; R ¹³ represents d-4 alkyl optionally substituted by a halogen atom); - Ph (Q is optionally substituted by binding or halogen atoms C - ₄ alkylene, Ph represents an optionally phenyl optionally substituted by halogen atom!); and optionally substituted by a halogen atom May be substituted with one or more substituents selected from good benzyl)

Represents

R ⁷ is

A hydrogen atom;

Cl @ - 4 alkylthio or C i - ₄ alkoxy (alkyl and alkyl moieties are their it halogen atom or C, - ₄ alkoxy (optionally substituted by may) be substituted by halogen atoms) substituted by ! which may be C - ₄ Aruki Lumpur; C! -4 alkoxycarbonyl optionally substituted by a halogen atom; C i-4 alkanol optionally substituted by a halogen atom; or

One C (= ^{〇) - N (- R 1 1} ) (- R 1 2) (R 1 1 and R ^{1 2} may be the same or different dates, _d-4-alkyl or d - ₄ alkoxy (said alkyl And the alkyl moiety may be substituted by a halogen atom).

Represents)

The compounds according to the invention are useful as pesticides.

Detailed description of the invention

Compound

The term “alkyl” or “alkoxy” as a group or part of a group means an alkyl or alkoxy group, wherein the group is straight, branched, or cyclic.

The C doctor ₄ alkyl, methyl, Echiru, n- Purobiru, linear alkyl, such as n- butyl, isopropyl, isobutyl, tert- branched chain alkyl such as butyl, Contact and cycloprothrin building, cyclic alkyl such as cyclobutyl Represents

d-4 alkoxy refers to linear alkoxy such as methoxy, ethoxy, n-propoxy, n-butoxy, branched alkoxy such as isopropyloxy, isobutyloxy, tert-butyloxy, and cycloproviroxy. Represents a cyclic alkoxy such as xy or cyclohexyloxy.

The halogen atom means a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

The saturated or unsaturated 5- or 6-membered heterocyclic ring means a heterocyclic ring containing at least one heteroatom selected from a nitrogen atom, an oxygen atom, and a sulfur atom. Examples of this complex ring include a pyridine ring, a furan ring and a thiophene ring.

As used herein, “alkyl optionally substituted with” means that one or more hydrogen atoms on the alkyl are substituted with one or more substituents (which may be the same or different). Mean good alkyl. It will be apparent to those skilled in the art that the maximum number of substituents can be determined depending on the number of substitutable hydrogen atoms on the alkyl. The same applies to groups having a substituent other than alkyl, for example, alkoxy, phenyl, and heterocyclic groups. R ¹ and R ² may be the same or different and preferably represent a C ₄ alkyl which may be substituted by a hydrogen atom or a halogen atom.

R ³ and R ⁴ may be the same or different and preferably represent a halogen atom.

R ⁵ preferably represents a hydrogen atom; an optionally substituted d-4 alkyl; or an optionally substituted phenyl.

The phenyl represented by R ⁶ is preferably 1-, 2- or 3-substituted by one or more substituents which may be the same or different. As used herein, “1, 2-, or 3-substituted” means substitution with one, two, or three substituents.

R ⁶ is preferably phenyl (which phenyl may optionally halogen atom (same or different dates); Shiano; nitro; halogen atoms which may be substituted by C, - ₄ alkyl; optionally substituted by a halogen atom Which is substituted by d-4 alkoxy, and is preferably substituted by 1, 2-, or 3-).

R ⁷ preferably represents a hydrogen atom or C ぃ₄ alkyl substituted by C ₄ alkylthio or C 4 alkoxy.

Preferred compounds of the formula (I) include:

R ¹ and R ² may be the same or different and each represents a Ci- ₄ alkyl which may be substituted by a hydrogen atom or a halogen atom,

R ³ and R ⁴ may be the same or different and represent a halogen atom,

R ⁵ represents a hydrogen atom; d- ₄ alkyl which may be substituted; or phenyl which may be substituted;

R ⁶ represents an optionally substituted phenyl and / or an optionally substituted 5 or 6 membered saturated or unsaturated heterocyclic group,

R ⁷ is a hydrogen atom; an optionally substituted C - ₄ alkyl (preferably, d ₄ § alkylthio or Ci ₄ good d ₄ alkyl optionally substituted by alkoxy);! May be substitution d- 4 alkoxycarbonyl; optionally substituted Ci-4 alkanoyl; or one (C = 〇) one NR R ¹² (R ¹¹ and R ¹² are as defined above.) A) is given.

More preferred compounds of the formula (I) include:

R ¹ and R ² represent a hydrogen atom,

R ³ and R ⁴ represent a halogen atom, for example, a chlorine atom,

R ⁵ represents unsubstituted d ₄ alkyl,

R ⁶ represents phenyl, which is a halogen atom (which may be the same or different); cyano; nitro; d-4 alkyl optionally substituted by a halogen atom; or substituted by a halogen atom. By d-4 alkoxy

1, 1, 2, or 3_ are substituted,

Compounds wherein R ⁷ represents d- ₄ alkyl substituted by a hydrogen atom or C ₄ alkoxy.

Specific examples of the compound of the formula (I) include the compounds listed in Table 1.

table 1

Object P.R, R ₆ R ₇

1 U π U π pi Π3 ~ i / V H o η u η U pi P11 Π3 * ± DI n U u

ο II pi u π π 1

A υ i pi

η η 1 ίΐ 3 乙 1 ノ n n

o pi PI

η π し 1 し 1 Λ 4 Ρ Ί _ ノ X.--

PI

Π π Π 1 1 O 1 n η 一 1 1 ill ώ ill 一

n

Q ττ

o π π then J_ ί3 4—1 Γ? — “no” 73 one n n lenno u n η Π 1 one 1 0! Γ?

IU η η

11 υ

1 η u η PI Π3 UX No 3 No u n

1 υ

η υ π 011 pi

Π3 Ul X No u n

1 on Q Η u νΠ3? Α-ΗΊ -F- "7-~"

Η J j 2-p-4-R _r-

15 Η Η C1 C1 4-c -Finish H

16 Η Η C1 C1 2— GFa-phenyl H

17 Η Η C1 C1 Cft 3- CFs-Feninole H

18 Η Η C1 C1 CHs 4-0CF3-7

19 Η Η C1 C1 CKJ 3-OC -Phenyl H 0 Η Η C1 C1 Cft 2-0CF ₃ -Phenyl H 1 Η Η C1 C1 C¾ 2-Br-4-CF ₃ -Phenyl H 2 Η Η C1 C1 Cft 2 -Br-4- 0CF ₃ -Phenyl H 3 Η Η C1 C1 CH3 2,6-di- C1- 4-CF ₃ -Phenyl H 4 Η Η C1 C1 Cft Phenyl H 5 Η Η C1 C1 CH3 4- C¾ -Phenyl H

Compound Ri R ₂ R ₃ Rt R ₅

¾

51 H H CI CI c¾ 2-F-4-Br-phenyl Cft

52 HH CI CI Cft 4- CF ₃ -phenyl C ニル

53 HH CI CI Cft 2- CF ₃ -phenyl Cft

54 HH CI CI Cft 3-CF ₃ -phenyl Cft

55 HH CI CI ca 4- 0CF ₃ -phenyl Cft

56 H H CI CI Cft 3-0CF3-phenyl c

57 H H CI CI CE 2- 0CF3 -phenyl

58 H H CI CI cm 4 1 Br—Feninole CH20CH3

59 H H CI CI Cft 3, 4-di-Cl-phenyl c ocft

60 H H CI CI Cft 2,4-di-Br-phenyl CHzOCft

61 H H CI CI Cft 2, 6-di-Br-phenyl CHzOCH)

62 HH CI CI Cft 2, 6-di- C1-4- CF ₃ -Phenyl CHzOCIt

63 H H CI CI CH3 2-F-4-Br-phenyl cmocit

64 HH CI CI c 4-CF ₃ -phenyl CHzOCft

65 HH CI CI Cft 2-CF ₃ -phenyl cmoca

66 HH CI CI Cft 3- CF ₃ -phenyl caocft

67 HH CI CI c¾ 4-0CF ₃ -phenyl cftoca

68 HH CI CI ca 3-0CF ₃ -phenyl caocft

69 HH CI CI Cft 2- 0CF ₃ -phenyl CH OCft

70 H H CI CI Cft 4-SCft-phenyl CH2OCH3

71 H H CI CI Cft 4-SOCHa-phenyl CHzOCIL

72 HH CI CI Cft 4-so ₂ ca-phenyl CH20CH3

73 H H CI CI CH3 4-CN-phenyl CHEOCIL

_{74 HH CI CI CH3 4- N0 2} - phenyl caocHs

75 HH CI CI Cft 4-Br-phenyl CHzOCHzCft Object P. R, X),

76 H H CI CI 4- CI-phenyl CHzOCHzCa

77 H H CI CI Cft 3,4-di-CI-phenyl

78 H H CI CI Cft 2,4-di-Br-phenyl cftocaca

79 H H CI CI ca 2,6-di-Br-phenyl cmociicft

80 HH CI CI c¾ 2,6-di-Cl-4-CF ₃ -phenyl C 0C¾CH3

81 H H CI CI Cft 2-F-4-Br-phenyl cHaOcacft

82 HH CI CI 4-CF ₃ -phenyl

83 HH CI CI 2-CF ₃ -phenyl ciiocacft

84 HH CI CI ca 3-CF ₃ -Phenyl CHzOCHzCE

85 H H CI CI 4-OCF "phenyl CH2OCH2CH3

86 HH CI CI CE 3-0CF ₃ -phenyl c ocacft

87 HH CI CI Cft 2-0CF ₃ -Phenyl CftOCftCiL

88 H H CI CI Cft 4-SCft-phenyl CftOC thigh

89 HH CI CI Cft 2-Br-4-CF ₃ -phenyl CH2OCH2CH3

90 HH CI CI CHi 2-Br-4-0CF ₃ -Phenyl CltOCHzCft

91 H H CI CI CHa 4-CN-phenyl caocaca

92 HH CI CI CHs 4-N0 2 - phenyl caocitcft

93 H H CI CI H 4-Br-phenyl H

94 H H CI CI H 4-C triphenyl H

95 H H CI CI H 3,4-di-Cl-phenyl H

96 H H CI CI H 2,4-di-Br-phenyl H

97 H H CI CI H 2,6-di-Br-phenyl H

98 H H CI CI H 2,4-di-F-phenyl H

99 H H CI CI H 2-F- 4-Br-phenyl H

100 HH CI CI H 4-CF ₃ -Phenyl H R,

u

_{101 HH CI CI H 2- CF 3} - phenyl H

_{102 HH CI CI H 3- CF 3} - Fuweniru H

103 HH CI CI H 4-0CF ₃ -Phenyl H

_{104 HH CI CI H 3- 0CF 3} - phenyl H

105 HH CI CI H 2-0CF ₃ -Phenyl H

106 H H CI CI H Phenyl H

107 H H CI CI H 2-CN-phenyl H

108 H H CI CI H 3-CN-phenyl H

109 H H CI CI H 4-CN-phenyl H

110 HH CI CI H 2-N0 2 - phenyl H

111 H H CI CI H 3-N02-phenyl H

112 HH CI CI H 4-N0 2 - phenyl H

113 H H CI CI H 3-pyridyl H

114 H H CI CI H 4, 6-di-C1-2-pyrimidyl H

115 H H CI CI H 4, 6-di-OCft-phenyl H

116 H H CI CI H 3-7 Ril H

117 H H CI CI H 3-Chenyl H

118 H H CI CI H 4-Br-phenyl Cft

119 H H CI CI H 3,4-di-Cl-phenyl Cft

120 HH CI CI H 4-CF ₃ -phenyl ca

121 HH CI CI H 2-CF ₃ -phenyl Cft

122 HH CI CI H 3-CF ₃ -phenyl CIL

123 HH CI CI H 4-0CF ₃ -Phenyl Cft

_{124 HH CI CI H 3- 0CF 3} - phenyl CtL

125 HH CI CI H 2--0CF ₃ -phenyl cm Compound E ₂ R ₃ R ₅ Re R ₇

126 H H CI ci H 4-1-Br—Feninole CH2OCH3

127 H H CI ci H 3, 4-di-Cl-Feninole CH2OCH3

128 HH CI ci H 2 4-di-Br- ^ ⁷ ene CH2OCH3

129 H H ci ci H 26-di-Br-phenyl CH2OCH3

130 H H CI CI H 4-CF3-αι 二) レ

H Γ1 CI H? -nFi- "7 ale

<J CI -PFi- "Ale

H CI H 4 One OCFi-phenyle

1 rtA IX u r] υ n Ί ΠΓΡ, ー: r le nzu H3

H Π CI

H H ci H 4-Br Br

1 37 H H CI ci H 4 1 C1-phenyl CH2OCH2CH3

H H Ί Fale

139 H H CI CI H 2 Br—Hue Kuni--/ L CH20CH2CH)

140 H H ci ci H 2,6— di— Br—Feninole CH20CH2CH3

141 H H ci ci H 4-CF3—Feninole CH20CH.CH!

142 H H ci ci H 2-CFJ-phenyl CftOCHjCft

143 HH CI CI H 3-CF ₃ -phenyl CHzOCH CH

144 HH CI CI H 4--0CF ₃ -phenyl c oc¾ca

145 H H CI CI H 3-OCF "phenyl CftOCHiCHs

146 HH CI CI H 2-0CF ₃ -phenyl cmociicit

147 H H CI CI CH2CH3 4-Br-phenyl H

148 H H CI CI CH2CH3 4-C1-phenyl H

149 H H CI CI CH2CH3 3,4-di-C1 -phenyl H

150 HH CI CI CH2CH3 2, 4-di-Br-phenyl H Compound R ₂ R3 R4 R ₅ Re R ₇ number

151 HH CI ci 4-CF ₃ -phenyl H

152 HH CI ci CH2CH3 2-CF ₃ -Phenyl H

153 H H CI ci CH2CH1 3-CF3-phenyl H

154 H H CI ci CH2CK1 4-0Cf Feninore H

155 HH CI ci CH2CH3 3-0CF ₃ -H2

156 H H ci ci CH2CH3 2-0CFi-phenyle H

157 H H CI CI CH2CH3 4-CN-7

158 H H ci ci CH2CH3 4-N02—Pheninole H

159 H H CI CI CH2CH3 Pheninole CH2OCH3

160 H H CI ci 3 4_di_Cl—Funere CH20CH3

161 H H ci ci CH2CH3 2 4-di Br

162 H H CI ci CHzCft 4-CF3—Pheninole CH20CH3

163 H H ci ci CHzCft 2-CF3-Pheninole CH20CH3

164 H H ci ci CH2CH3 3-CF3-phenyl CHzOCIt

165 H H ci ci CH2CH3 4-0CF3-phenyl CH2OCH3

166 H H ci CI CH2CH3 3-0CF3-phenyl cmocm

167 H H CI CI CH2CH3 Phenyl cHzOc

168 H H CI CI CH2CH3 4-CN-phenyl c ocft

169 HH CI CI CH2CH3 4-N0 2 - phenyl citoca

170 H H CI CI CHzCHa 4-Br-phenyl

171 H H CI CI CH2CH3 4-C1-phenyl c¾oc thigh

172 H H CI CI CH2CH3 3,4-di-C triphenyl CHzOC thigh

173 H H CI CI CH2CH3 2 4-di-Br-phenyl CHaOCltCft

174 HH CI CI CH2CH3 4-CF ₃ -phenyl cftocacm

175 HH CI CI CH2CH3 2_CF ₃ -Phenyl

Compound Ri Λ2 & 3 R4 R5

Number

201 H c¾ CI CI CH2CH3 3- 0CF ₃ -phenyl CH2OCH3

202 H c¾ CI CI CHzCHi 2-0CF ₃ -Phenyl CftOCH,

203 H CH3 CI CI CH2CH3 4-CN-phenyl CH2OCH3

204 H Cft CI CI CH2CH3 4- N0 2 - phenyl c oca

205 H C¾ CI CI CH2CH3 4-Br-phenyl jikOChzCm

206 H Cft CI CI CH2CH3 4-C1-phenyl CHzOCHzCHa

207 H Cli CI CI CHzCiL 3,4-di-Cl-phenyl CHzOC

208 H Cft CI CI CH2CH3 2,4-di-Br-phenyl CHzOCHzCa

209 H C¾ CI CI CH2CH3 4-CF ₃ -Phenyl CaOCHzCHa

210 H Cft CI CI CH2CH3 2-CF ₃ -phenyl caocHzca

211 H c¾ CI CI then nzCIL 3-CF ₃ -phenyl CftOCItCft

212 H Cft CI CI CH2CH3 4-0CF ₃ -phenyl CftOCftCHj

213H CH3 CI CI 3-0CF ₃ -phenyl cHzOcacit

214H CH3 CI CI CH2CH3 2-0CF ₃ -phenyl caocacft

215 H Cft CI CI CH2CH3 4-CN-phenyl CftOClLCft

216 H Cft CI CI CH2CH3 4- N0 2 - phenyl CHzOC

217 Cft C¾ CI CI H 4-Br-phenyl H

218 C¾ Cft CI CI H 4-C1-phenyl H

219 Cft CI CI H 3,4-di-Cl-phenyl H

220 cm CE CI CI H 2, 4-di-Br-phenyl H

221 Cft Cft CI CI H 4-CFrphenyl H

222 Cft Cft CI CI H 2-CF ₃ -Phenyl H

223 C¾ Cft CI CI H 3-CF ₃ -Phenyl H

224 Cft CHJ CI CI H 4-0CF ₃ -Phenyl H

225 Cft Cft CI CI H 3-0CF ₃ -phenyl .H

/ Shihachi

Compound Ri 1 2 R3 R4 Rs R6 R?

251 Cft ca CI CI H 4- N0 2 - phenyl CH2OCH2CH3

252 H H CI CI C I 4-Br-phenyl H

253 H H C I CI C I 4-C 1 -phenyl H

254 H H CI CI C I 3, 4-di-Cl-phenyl H

255 H H CI CI CI 2, 4-di-Br-phenyl H

256 HH CI CI CI 4-CF ₃ -Phenyl H

257 HH CI CI CI 2-CF ₃ -Phenyl H

258 H H CI CI C I 3-CF "Phenyl H

259 HH CI CI CI 4-0CF ₃ -Phenyl H

260 HH CI CI CI 3-0CF ₃ -Phenyl H

261 HH CI CI CI 2-0CF ₃ -Phenyl H

262 H H CI CI CI 4-CN-phenyl H

263 HH CI CI CI 4-N0 2 - phenyl H

264 H H Br Br Cft 4-Br-phenyl H

265 H H Br Br Cft 4-U-phenyl H

266 H H Br Br Cft 3,4-di-C triphenyl H

267 H H Br Br CHa 2,4-di-Br-phenyl H

268 HH Br Br Cft 4-CF ₃ -Phenyl H

269 HH Br Br Cft 2- CF ₃ -phenyl H

270 HH Br Br c 3-CF ₃ -Phenyl H

271 HH Br Br CH3 4-0CF ₃ -Phenyl H

272 HH Br Br CH3 3-0CF ₃ -Phenyl H

273 HH Br Br cm 2-0CF ₃ -Phenyl H

274 H H Br Br Cft 4-CN-phenyl H

_{275 HH Br Br Cft 4- N0 2} - phenyl H

Compound Ri R ₂ R3 R ₅ R ₇ Qϋ tu 12 1 2 nuni ¾ DI

OQQ u n 1I P1

Π2 Π3 ί13 4-Ρ11-"7 Πζυ Πζυ2 Γ13

OUU Γ1 Π2 ni

Π Π 3 丄 α αι 丄ェェ tl tl tl2U ΐ 3 Π Π 2 Π 3 丄 3 f * *! Ίΐ3 3 αι ur no —α Π2 Π3 u u n il2 2 Ha 1 し 1 3 4 ί * 3 3 * 3 ノ x.

P1

lio n ίΐ2 tl3 1 1 it it し! it!! L * 3 L L L L L L 3 3 3 L L L 3 L L L L L ίΐ2 tl3 ne u nnrs nu n 112 112 ill ill i 丄 J J 4-U 1 1 ^ 3-no H H2U U U3

Π ίΐ 2 ίΐ 3 ίΐ 1 0

J 一 J * * J * * * * * * * * * *

OU / a then tl2 then ίΐ3 p then i 1 p then i 1 then Ha U then f3 no one then il2U then ίΐ3 u pi

όυο n Π2 113 113 1 1 丄 ila 一一 J-PI 3 u PI

n ίΐ 2 し 3 丄 1 4 4 J U2 Nore tkU H H2 tl3 1 n nu υ π P P nu u u 0iU 丄 I 丄 1

1 1 Q3 L ₉ u Ql · · — Π

911 u

n Π U

1 1 Π3 ώ 43-Η Uίi-Ί-"7 —one J) / Π U

Q1 u n U π 1 Π3 o 0 ς-Η U.1ϊ -P1-"1 u1 ϋ ϋ Η 1 P1 P 9 -Pl-" Ale a

Ί14 "H Η C11 C1 0¾ 5— di-Cl—phenyl H

315 H Η C1 C1 94 fi-tri-Gl-f: r

316 H Η C1 C1 Cft 234 one tri one C1 one fennore H

317 H Η C1 C1 c 245-tri-Cl-phenyl H

318 H Η C1 C1 c¾ 3,45-tri-Cl-phenyl H

319 H Η C1 C1 en 2-CF ₃ -phenyl H

320 H Η C1 C1 CH3 3-CF Factory Fan H Compound Ri R ₂ R ₅ Rs

Number

321 HH CI CI Cft 3, 5-di-CF ₃ -phenyl H

322 H H CI CI CE 3-CF3- 4- CI-phenyl H

323 H H CI CI CH3 4- OCHF2-phenyl H

324 H H CI CI Cft 4- (4-0CF3-phenoxy) -phenyl H

325 H H CI CI CIL 4- (3-0CF3-phenoxy) -phenyl H

326 H H CI CI Cft 2-C1 JL

327 PI H F F C¾ 2-CF3-phenyl H

328 H H F F CH, 3-CFi-Pheninole H

329 H H F F Cft 4-CFa-phenyl H

330 H H F F CHJ 2 0CF3—phenylene H

331 H H F F Cft 3— OCFs—phenylene H

332 H H F F Cft 4-OCFa-Feninore H

333 H H F F CIL 2— CI—Pheninole H

334 H H F F Cft 3-C1-phenyl H

335 H H F F Cft 4-C1-phenyl H

336 H H F F c¾ 3 4-di-Cl-phenyl H

337 H H F F ca 2-Br-phenyl H

338 H H F F Cft 3-Br-phenyl H

339 H H F F CIL 4-Br-phenyl H

340 H H F F CIL 2,4-di-Br-phenyl H

341 H H F F cm 2 6-di-Br-phenyl H

342 HHFF CHa 26-di -Cl-4-CF ₃ -phenyl H

343 HHFF 2-CF ₃ -phenyl CHzOCECHs

344 HHFF Cft 3- CF ₃ -phenyl C¾0C¾CH ₃

345 HHFF CH3 4- CF ₃ - Fuweniru caocaca

匕合物 Ri K3 R4 Rs lie R?

396 HH CI CI Cft 4-CF ₃ -phenyl cocHzcaci

397 HH CI CI Cft 4- CF ₃ -phenyl COCH (Cft) ²

398 HH CI CI CHa 4-CF ₃ -phenyl COCMCft

399 HH CI CI cm 4-CF ₃ -phenyl COCHiOCOCft

400 HH CI CI 4-CF ₃ -phenyl cocascit

401 HH CI CI CH3 4-CF ₃ -phenyl CH2CH3

402 HH CI CI 4- CF ₃ -phenyl CH (Cft) ₂

403 HH CI CI CH3 4-CF ₃ -Phenyl

404 HH CI CI Cft 4-CF ₃ -Phenyl C0N (Cft) ₂

405 HH CI CI CH3 4-CF ₃ -Phenyl C0N (C2¾) ₂

406 HH CI CI Cft 4-CF ₃ -Phenyl C0N (0Cft) CH3

407 HH CI CI Cft 4-CF ₃ -phenyl CH ₂ 0CftCH = CH ₂

408 HH CI CI CH3 4-CF ₃ -phenyl cfiocacscH

409 HH CI CI Cft 4-CF ₃ -phenyl CH ₂ 0CH (Cft) ₂

410 HH CI CI c¾ 4- CF ₃ -phenyl Cft0C0C (CH3) ₃

411 HH CI CI CE. 4-CF ₃ -phenyl caococacHzcac

412 HH CI CI CH3 4-CF ₃ -phenyl coscHacm

The compounds of formula (I) can form salts. Examples of the salt of the compound of the formula (I) include alkali metal salts such as lithium salt, sodium salt and potassium salt; alkaline earth metal salts such as magnesium salt and calcium salt; ammonium salt, methyl ammonium salt and dimethyl ammonium salt. Ammonium salts such as trimethylammonium salt, dicyclohexyl ammonium salt; triethylamine, trimethylamine, diethylamine, pyridine, ethanolamine, triethanolamine, dicyclohexylamine, proforcein, benzylamine, N Organic amine salts such as —methylbiperidine, N-methylmorpholine, and getylaniline; and basic amino salts such as lysine, arginine, and histidine.

The compounds of formula (I) can form solvates, for example hydrates or ethanolates.

Isomers, such as geometric isomers, may exist in the compounds of formula (I), but any such isomers and mixtures thereof are also encompassed by the present invention.

Manufacture of compounds

The compound of the formula (I) can be produced according to the method described in JP-A-9-144032.

For example, it can be manufactured according to the following method.

Compounds of formula (I) wherein R ⁷ is hydrogen are substituted cyclopropane carboxylic acid derivatives of formula (II):

And a compound of formula (III) (eg, diazonium salt of aniline)

.R ⁶

(HI) in an appropriate reaction solvent (for example, water or a mixed solvent of water and an organic solvent) whose pH has been adjusted to 4 to 8 with sodium acetate, sodium carbonate, etc., from —20 ° C. It can be produced by reacting at room temperature.

The compound of the formula (I) in which R ⁷ is substituted by a substituent is obtained by the compound obtained by the above step. Compound (R ⁷ is a hydrogen atom) in the presence of an appropriate base such as potassium carbonate, sodium hydroxide, potassium ethoxide, potassium t-butoxide, and a halide: Ha 1 — R ⁷ (R 7 is a hydrogen atom) Which represents a substituent other than).

The substituted cyclopropane carboxylic acid derivative of formula (II) can be prepared by the method described in Synthesis, (1977), 472 and Synthesis, (1983), 308, wherein the ester of substituted cyclopropane carboxylic acid of formula (IV) (W - 0- C - ₄ represents an ester residue such as alkyl) or salt product (W represents a halogen atom such as chlorine)!:

Acetonitrile in the presence of a base such as sodium-butyllithium hydride

Alternatively, it can be produced by reacting with cyanoacetic acid.

The compound of the formula (IV) is disclosed in JP-B-55-42444, JP-A-62-210855, JP-A-63-54350. It can be manufactured according to the method described.

Specifically, when W is an ester residue, the compound of the formula (IV) is substituted with a compound of the formula (V) which is commercially available or can be obtained by a known synthesis method.

(R represents 4 alkyl, etc.) with a compound capable of generating a carbene, for example, sodium trichloroacetate or sodium difluorochloroacetate at an elevated temperature (for example, about 100 ° C. to about 200 ° C.) Alternatively, it can be produced by reacting with 50% sodium hydroxide in a chloroform form in the presence of a phase transfer catalyst such as triethylbenzylammonium chloride. The compound of the formula (IV) in which W is a chlorine atom can be produced by hydrolyzing the compound obtained in the above step and then hydrolyzing it with thionyl chloride or the like.

A compound of formula (III) wherein R ⁶ is optionally substituted phenyl, for example anily The diazonium salt of aniline can be prepared by adding an aqueous solution of sodium nitrite to the hydrochloride or sulfate of aniline in water or a mixed solvent of water and an organic solvent kept at about −10 to about 1 ° C. Can be manufactured. Compounds of formula (III) in which R ⁶ is an optionally substituted 5- or 6-membered saturated or unsaturated heterocyclic group can likewise be prepared.

Compound applications

The compound of the formula (I) has an excellent control effect on pests such as pests and phytopathogenic microorganisms. Therefore, the compounds of the formula (I) are useful as pesticides.

The compounds of the formula (I) have an excellent control effect against pests, in particular agricultural pests, sanitary pests, storage pests, clothing pests and house pests. Thus, the compounds of formula (I) can be used as insecticides, centrifugal and acaricides. Examples of pests include lepidopteran pests (eg, Lotus cutworm, Spodoptera, Acapulcum, Aomushi, Konaga, Japanese beetle, etc.),

Hemiptera pests (eg, peach aphids, blue aphids, brown beetle power, stag beetle, brown beetle power, stag beetle, etc.),

Coleoptera insects (for example, rice worms, azuki worms, stalkworms, etc.),

Acarid pests (for example, Namihadani, Kanzadahada2, Ranunhadani, etc.),

Diptera pests (for example, houseflies, etc., plant parasitic nematodes, for example, cat flies, negusarecenti, rice singaresyu, pine moss, etc.)

Is mentioned.

The compounds of the formula (I) have an excellent control effect against plant disease fungi. Therefore, the expression

The compounds (I) can be used as fungicides and fungicides. Examples of plant disease fungi include microorganisms such as rice blast fungus, rice sheath blight fungus, cucumber anthracnose, cucumber downy mildew, cucumber powdery mildew, and wheat leaf rust.

The compounds of the formula (I) show excellent control activity against harmful weeds. Thus, the compounds of formula (I) can be used as herbicides and herbicides. Examples of the harmful weeds include plants such as Mehishino, Enokorogusa, Ooinuyu, Kosendangusa, American Sendangusa.

When the compound of the formula (I) is used as an active ingredient of a pesticide, the compound of the formula (I) Either use the compound as it is, or mix it with an appropriate solid carrier, liquid carrier, gaseous carrier, surfactant, dispersant, or other formulation aids to prepare emulsions, solutions, wettable powders, powders, granules, oils Use it in any dosage form such as aerosol, flowable and so on.

Examples of the solid carrier include talc, benite, clay, kaolin, diatomaceous earth, bamboo silicate, white carbon, calcium carbonate and the like.

Examples of the liquid carrier include alcohols such as methanol, n-hexanol and ethylene glycol; ketones such as acetone, methyl ethyl ketone and cyclohexanone; and aliphatic hydrocarbons such as n-hexane, kerosene and kerosene. Aromatic hydrocarbons such as toluene, xylene and methylnaphthylene, ethers such as getyl ether, dioxane and tetrahydrofuran, esters such as ethyl acetate, nitriles such as acetonitrile and isobutyronitrile, dimethylformamid Acid amides such as dimethylacetamide, vegetable oils such as soybean oil and cottonseed oil, dimethylsulfoxide, water and the like.

Examples of the gas carrier include LPG, air, nitrogen, carbon dioxide, dimethyl ether and the like.

Examples of surfactants and dispersants for emulsification, dispersion, spreading, etc. include alkyl sulfates, alkyl (aryl) sulfonates, polyoxyalkylene alkyl (aryl) ethers, and polyhydric alcohol esters. , Lignin sulfonate and the like can be used.

Further, as an adjuvant for improving the properties of the preparation, for example, carboxymethyl cellulose, gum arabic, polyethylene glycol, calcium stearate and the like can be used.

The carrier, surfactant, dispersant, and auxiliary can be used alone or in combination as necessary.

The content of the active ingredient in the preparation is usually 1 to 75% by weight for emulsions, usually 0.3 to 25% by weight for powders, 1 to 90% by weight for wettable powders, and usually 0.1 to 90% by weight for granules. It can be 5 to 10% by weight.

The formulation according to the invention may contain other formulations such as other insecticides, fungicides, acaricides, herbicides, plant growth regulators, fertilizers and the like. The preparation according to the present invention can be used as it is or after dilution. The preparations of the present invention may be used in admixture with other preparations such as other insecticides, fungicides, acaricides, herbicides, plant growth regulators, fertilizers, and the like.

The present invention also provides a method for controlling pests, comprising treating an area to be protected from pests with an effective amount of a compound of formula (I) or a salt or solvate thereof. You. The treatment of the protected area can be carried out by spraying on farmland or injecting into soil.

Example

The production examples, preparation examples, and test examples of the compound according to the present invention are illustrated below as examples, but the present invention is not limited to these examples.

Reference Example 1: Production of 3- (2,2-dichrolic-1-methylcyclopropyl) -13-oxopropanenitrile

Ethyl methacrylate (40 ml) and triethylbenzylammonium chloride (2 g) were dissolved in black-mouthed form (200 ml), and heated at 40 ° C to 50% potassium hydroxide (220 g). Was slowly added dropwise, and after the addition was completed, the mixture was further stirred for 10 hours. The reaction solution was poured into ice water, extracted with ethyl acetate, the ethyl acetate layer was washed with saturated saline, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to give 2,2-dichloro-1-methylcyclohexane. A crude product of ethyl propanecarboxylate (57 g) was obtained.

A 60% sodium hydride (4.4 g) was suspended in tetrahydrofuran (100 ml), and the mixture was refluxed to obtain a crude product of ethyl 2,2-dichloro-1-methylcyclopropanecarboxylate (22 g) and acetonitrile (5 ml). Was dissolved in tetrahydrofuran (20 ml) and added dropwise. After refluxing for 3 hours and cooling, the reaction solution was poured into ice water (500 ml), acidified with 1N hydrochloric acid, and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated saline, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain a crude product. The crude product was purified by column chromatography (co-gel C—200 100 ml, elution solvent: n-hexane: ethyl acetate = 5: 1), and the product was purified by 3— (2,2-dichloromethane 1—1). Methylcyclopropyl) 1-3-oxopropane nitrile (9.5 g) was obtained.

- NMR (solvent; CD C 1 ₃₎

δ = 3.84 (1Η, d), 3.69 (1H, d), 2.33 (1Η, d), 1. 6 5 (3H, s), 1.47 (1 H, d)

Synthesis Example 1: Preparation of Compound 15

Under ice cooling, 4-trifluoromethylaniline (322 mg) was suspended in 10% hydrochloric acid (3 ml), and sodium nitrite (138 mg) was dissolved in water (0.5 ml) and added dropwise. After stirring at 5 ° C or less for 30 minutes, 3- (2,2-dichloro-1-methylcyclopropyl pill) -13-oxopropanenitrile (384 mg), methanol (3 ml), sodium acetate (15 Omg), water ( (1 ml) was added dropwise, and the mixture was stirred at room temperature for 15 hours. The crude product precipitated in the reaction solution was obtained by filtration under reduced pressure, purified by column chromatography (100 mg of Cogel C-200, elution solvent n-hexane: ethyl acetate = 3: 1), and further purified by column chromatography. Recrystallization from η-hexane monoethyl acetate gave Compound 15 (158 mg).

Ή-NMR (solvent; CD C 1 ₃₎

5 = 9.5 1 (1H, br.s), 7.74 (2H, d), 7.57 (2H, d), 2.17 (1H, d), 1.72 (3H , S), 1.52 (1 H. d) Synthesis example 2: Preparation of compound 34

Under ice-cooling, 412 troaniline (325 mg) was suspended in 10% hydrochloric acid (3 ml), sodium nitrite (25 Omg) was dissolved in water (1 ml) and added dropwise. After stirring at 5 ° C or less for 30 minutes, 3- (2,2-dichloro_1-methylcyclopropyl) -13-oxopropanenitrile (30 Omg), methanol (3 ml), sodium acetate (15 Omg) A mixture of water and water (1 ml) was added dropwise, and the mixture was stirred at room temperature for 15 hours. The crude product precipitated in the reaction solution was obtained by filtration under reduced pressure, and purified by column chromatography (Pecogel C-1 200 10 Oml, elution solvent n-hexane: ethyl acetate = 3: 1), and further n Recrystallization from hexane-ethyl acetate gave Compound 34 (28 Omg).

Ή-NMR (solvent; CDC 1 ₃₎

(5 = 9.69 (1H, br.s), 8.35 (2H, d), 7.55 (2H, d) 2.16 (1H, d), 1.71 (3H, s), 1.52 (1 H, d)

Synthesis Example 3: Production of Compound 74

Compound 34 (3 Omg) was dissolved in tetrahydrofuran (5 ml), and (250 mg), and the mixture was stirred at room temperature for 1 hour. Chloromethyl methyl ether (0.5 ml) was added, and the mixture was further stirred at room temperature for 15 hours. The reaction solution was poured into water, extracted with ethyl acetate, the ethyl acetate layer was washed with saturated saline, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain a crude product. Purification by column chromatography (Picogel C-200 60 ml, elution solvent n-hexane: ethyl acetate = 10: 1) gave Compound 74 (19.3 mg).

Ή-NMR (solvent; CDC 1 ₃₎

6 = 8.28 (2H, d), 7.65 (2H, d), 5.61 (1H, d), 5.

45 (1 H, d), 3.46 (3 H, s), 2.12 (1 H, d), 1.66 (3

H, s), 1.42 (1 H, d)

Synthesis Example 4: Compound 82

Compound 15 (5 Omg) was dissolved in tetrahydrofuran (5 ml), and thereto was added lithium carbonate (25 Omg), and the mixture was stirred at room temperature for 1 hour. Chloromethyl ethyl ether (0.5 ml) was added, and the mixture was further stirred at room temperature for 15 hours. The reaction solution was poured into water, extracted with ethyl acetate, the ethyl acetate layer was washed with saturated saline, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain a crude product. Purification by column chromatography (Picogel C-2006 Oml, elution solvent n-hexane: ethyl acetate = 10: 1) gave Compound 82 (41.4 mg).

'H- NMR (solvent; CDC 1 ₃₎

6 = 7.68 (2H, d), 7.56 (2H, d), 5.54 (1H, d), 5.42 (1H, d), 3.74 (lH, m) , 3.65 (1 H, m),

2.10 (1H, d), 1.57 (3H, s), 1.36 (1H, d), 1.21 (3H, m)

Synthesis Example 5: Compound 93

Dissolve cyanoacetic acid (lg) in tetrahydrofuran (80 ml) and cool to 70 ° C under an argon stream. 2. A 5M n-butyllithium hexane solution (9.2 ml) was added dropwise, and the temperature was gradually raised to 0 ° C, followed by stirring for 30 minutes. The mixture was cooled again to -70 ° C, 2,2-dichlorocyclopropanecarboxylic acid chloride (lg) was added, the temperature was gradually raised to room temperature, and the mixture was stirred for 1 hour. Pour the reaction mixture into ice water and add ethyl acetate After extraction, the ethyl acetate layer was washed with saturated saline solution, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain crude 3- (2,2-dichlorocyclopropyl) -3-oxopropane nitrile. (0.8 g) was obtained.

Under ice cooling, 4-promoaniline (1.1 g) was suspended in 10% hydrochloric acid (9 ml), and sodium nitrite (450 mg) was dissolved in water (3 ml) and added dropwise. After stirring at 5 ° C or less for 30 minutes, a mixture of crude 3- (2,2-dichlorocyclopropyl) -13-oxopropane nitrile (500 mg), methanol (5 ml), sodium acetate (500 mg), and water (2 ml) The solution was added dropwise and stirred at room temperature for 15 hours. The crude product precipitated in the reaction solution was obtained by filtration under reduced pressure, and purified by column chromatography (100 ml of Cogel C-200, elution solvent n-hexane: ethyl acetate = 3: 1), and further purified by n- Recrystallization from hexane-ethyl acetate gave Compound 93 (6 Omg).

Ή-NMR (solvent; CD C 1 ₃₎

6 = 9.44 (1H, br.s), 7.57 (2H, d), 7.28 (2H, d), 3.49 (1H, t), 2.30 (1H, dd), shows starting material 1. 96 (1 H, dd) compounds synthesized in the same manner, synthetic methods, and the ¹ H- NMR spectra in table 2.

In the table, A indicates that the compound was synthesized according to the methods described in Synthesis Examples 1 and 2. B indicates that the compound was synthesized according to the methods described in Synthesis Examples 3 and 4. C indicates that the compound was synthesized according to the method described in Synthesis Example 5.

Formulation Example 1: wettable powder

Compound of the present invention (Compound 1) 25% by weight

Clay 30% by weight

Diatomaceous earth 35% by weight

3% by weight calcium lignin sulfonate

Polyoxetylene alkyl aryl ether 7% by weight

Was uniformly mixed and pulverized to obtain a wettable powder.

Formulation Example 2: Powder

Compound of the present invention (Compound 1) 2% by weight

60% by weight of clay

Talc 3 7% by weight

Calcium stearate

Was uniformly mixed to obtain a powder.

Formulation Example 3: Emulsion

Compound of the present invention (Compound 1) 20% by weight

N, N-dimethylformamide 20% by weight

Xylene 50% by weight

Polyoxetylene alkyl aryl ether 10% by weight

And uniformly mixed and dissolved to obtain an emulsion.

Formulation Example 4: Granules

Compound of the present invention (Compound 1) 5% by weight

Bentonite 40% by weight

Talc 5 3% by weight

Lignin sulfonate calcium

After uniformly pulverizing and mixing, water was added and kneaded well, and the mixture was granulated and dried to obtain granules. Test example 1: Pine moth control test

Spray the test compound diluted to 100 ppm with 50% acetone water (adding 20% 0.05%) to a cabbage leaf disk 5 cm in diameter in a plastic cup with a spray gun. Air dried. Release 10 second instar larvae in a cup Then, the animals were covered and kept in a constant temperature room at 25 ° C. Three days after the treatment, the larvae were observed for life and death, and the mortality was calculated.

As a result, those showing an activity with a mortality of 80% or more are shown below.

Compounds 2, 3, 5, 8, 10, 1 1, 14, 15, 18, 19, 21 22, 23, 26, 31 1, 34, 39, 52, 64, 67, 82, 85, 90, 93, 95, 183, 186, 189, 280, 284, 290, 293, 31 1, 3 12, 314, 3 15, 316, 317, 318, 319, 320, 32 1, 322, 323, 324 , 325, 329, 332, 345, 348, and 39 Test Example 2: Lotus cutworm control test

The test compound diluted to 200 ppm with 50% acetone water (tween en 20 0.05% added) was sprayed on a cabbage leaf disk 5 cm in diameter in a plastic cup with a spray gun and air-dried. In the cups, five third-stage larvae of the cutworm, Spodoptera litura, were released, covered and kept in a constant temperature room at 25 ° C. Three days after the treatment, the larvae were observed for life and death, and the mortality was calculated.

Compounds 2, 10, 11, 15, 18, 21, 22, 52, 64, 67, 82, 90, 93, 280, 284, and 31 1.

Test example 3: Peach control test

A test compound diluted to 50 ppm with 50% acetone water (adding 0.05% of Tween 20%) to a 5 cm diameter cabbage leaf disk in a plastic cup was sprayed with a spray gun and air-dried. Ten peach aphid first-instar larvae were released into the cup, covered and kept in a constant temperature room at 25 ° C. Three days after the treatment, the larvae were observed for survival and the mortality was calculated.

Compounds 1, 3, 5, 8, 10, 15, 18, 19, 21, 22, 26, 30, 93, 315, 320, 322, 329, 332, and 348.

Test example 4: Trifoliate control test

Place a 2 cm diameter finger leaf disc on agar, and place two female adults 1 0 animals were inoculated. After spawning in a constant temperature room at 25 ° C for 24 hours, female adults were removed, and the test compound diluted to 100 ppm with 50% acetone water (tween 200.05% added) was sprayed with a spray gun. . Seven days after the treatment, the hatching state of the eggs, the larvae and nymphs were observed, and the unhatched egg rate and the larval mortality rate were calculated, and the sum of these was defined as the insecticidal rate.

The following shows that the insecticidal rate showed an activity of 80% or more.

Compounds 2, 15, 18, 67, and 85.

Test example 5: Rice blast control test

After sowing in a plastic pot containing the culture soil, the seedlings were raised for about 15 days, and rice (cultivar: Toseki) in which three leaves were completely developed was used as a test plant. After spraying 10 ml per 3 pots of a drug solution diluted to 10 ppm with 10% acetone water (added with neoesterin 2000 times) to a concentration of 100 ppm using a spray gun, air-dried, and rice blast The conidia suspension (1 to 5 × 10 ⁶ / ml) collected and prepared from the petri dish in which the disease was cultured was uniformly inoculated by spraying and allowed to stand in a humidity chamber at 25 ° C. for 24 hours. After that, the disease was transferred to an artificial weather chamber at 20 ° C during the night and 25 ° C during the day, and the disease was caused.After 7 days from the inoculation, the number of lesions on the third leaf was counted. did.

Control value = (1 number of lesions in one treated area / number of lesions in untreated area) x 100

As a result, compounds having a control value of 80 or more are shown below.

Compounds 1, 2, 3, 5, 8, 10, 11, 12, 14, 15, 18, 19, 23, 24, 26, 31, 34, 35, 37, 38, 64, 67, 82, 85 , 2 90, and 293.

Test Example 6: Cucumber and disease control test

After seeding in a plastic pot containing the culture soil, seedlings were raised for about 10 days and cotyledons were completely developed. 10% acetone water

Spray 5 ml per 3 pots of a chemical solution prepared with 200 ppm (neoesterin added 2000 times) using a spray gun, air-dry, and collect from the leaves of Cucumber, which had previously developed downy mildew. , prepared conidia suspension (l~5 xl 0 ⁶ / ml) was uniformly inoculated by spraying and allowed to stand for 24 hours in a room humidity 2 1 ° C. Then night Transfer to an artificial climate chamber at 18 ° C during the day and 22 ° C during the day to cause disease.After inoculation 7, the diseased area in cotyledons is investigated and an index is given according to the following criteria. The control value was calculated.

Index 0: No lesion

1: Several lesions

2: Diseased area is less than 1/4 of leaf area

3: Diseased area is 1Z 4 or more and less than 1/2 of leaf area

4: Diseased area is more than 1/2 of leaf area and less than 3 Z4

5: Diseased area is 3/4 or more of leaf area

Incidence-∑ (index X number of strains) / (number of surveyed stocks X 5) X I 0 0

Control value = (1 disease severity in one treatment area / severity in untreated area) x 100

As a result, compounds with a control value of 80 or more are shown below.

Compounds 1, 2, 3, 4, 5, 6, 8, 11, 12, 19, 24, 25, 290, 313, 314, 315, and 319.

Test Example 7: Wheat leaf rust control test

Wheat seedlings (variety: Kanto No. 61), which were seeded in plastic pots containing culture soil, raised for about 14 days, and the third leaves were completely developed, were used as test plants. A spray solution of 10 ml of a drug solution adjusted to 200 ppm with 10% aqueous acetone (neoesterin added 2000 times) was sprayed using a spray gun for 10 ml per 3 pots, air-dried, and then wheat rust was previously detected. harvested from wheat leaves which had been ill, prepared summer spore suspension (l~5x l 0 ⁶ Zml) was uniformly inoculated by spraying and allowed to stand for 24 hours in a room humidity 21 ° C. The disease was then transferred to a climate chamber at 18 ° C at night and 22 ° C during the day to cause disease. 14 days after the inoculation, the diseased area of the third leaf was investigated, and the control value was calculated as in the case of cucumber and disease.

As a result, compounds with a control value of 80 or more are shown below.

Compounds 2, 11, 14, 15, 21, 22, 26, and 31.

Claims

The scope of the claims

1. Compounds of formula (I) and salts and solvates thereof.

(In the above formula,

RR ² , R ³ , R ⁴ , and R ⁵ may be the same or different, and include a hydrogen atom;

A halogen atom;

D-4 alkyl optionally substituted by a halogen atom; or

a phenyl which may be substituted by d-4 alkyl or d-4 alkoxy (the alkyl and the alkyl moiety may be substituted by a halogen atom),

However, I ¹ , RR ³ , R ⁴ , and R ⁵ do not all represent a hydrogen atom, and R ⁶ is

Phenyl (this phenyl is a halogen atom; d- ₄ alkyl optionally substituted by a halogen atom; C ₄ alkoxy optionally substituted by a halogen atom; cyano; nitro; amino; one S (= 〇) n—R ¹³ (n represents 0, 1, or 2; R ¹³ represents d— ₄ alkyl optionally substituted by a halogen atom); —OQ-Ph (Q represents a bond or substituted by a halogen atom May be C

! - ₄ alkylene, P h is a halogen atom represent an optionally phenyl substituted by); optionally substituted by one or more substituents selected from Njiru base may be substituted by a halogen atom Good); or

5- or 6-membered saturated or unsaturated heterocyclic group (this heterocyclic group is a halogen atom; d- ₄ alkyl optionally substituted by a halogen atom; C optionally substituted by a halogen atom.ぃ₄ alkoxy; cyano; nitro; amino; one S (= 0) nR ¹³ (n represents 0, 1, or 2; R ¹³ is substituted by a halogen atom Represents an optionally substituted C ₄ alkyl); — O— Q— Ph (Q represents an alkylene which may be substituted by a bond or a halogen atom, and Ph represents a phenyl which may be substituted by a halogen atom. And may be substituted with one or more substituents selected from benzyl which may be substituted with a halogen atom.)

Represents

R ⁷ is

A hydrogen atom;

Alkylthio or C i-4 alkoxy (the alkyl and alkyl moieties each of which may be substituted by a halogen atom or 〇ぃ₄ alkoxy (which may be substituted by a halogen atom)) ! — 4 alkyl;

An alkoxycarbonyl optionally substituted by a halogen atom; a C! -4 alkanoyl optionally substituted by a halogen atom; or

One C (= 0) One N (—R ¹¹ ) (—R ¹² ) (R ¹¹ and R ¹² may be the same or different, and d-4 alkyl or alkoxy (the alkyl and alkyl moiety is a halogen atom May be substituted by))

Represents)

2. The compound _{C according} to claim 1, wherein R ¹ and R ² may be the same or different and represent d-4 alkyl optionally substituted by a hydrogen atom or a halogen atom.

3. The compound according to claim 1, wherein R ³ and R ⁴ may be the same or different and each represents a halogen atom.

4. R ⁵ is a hydrogen atom; may be substituted by a halogen atom _d-4 alkyl le; or _d-4 alkyl (the alkyl may optionally be substituted by a halogen atom) or _d-4 alkoxy (which alkyl The moiety according to claim 1, wherein the moiety represents phenyl optionally substituted by: Compound.

5. R ¹ and R ² may be the same or different and each represents a Ci-4 alkyl optionally substituted by a hydrogen atom or a halogen atom,

R ³ and R ⁴ may be the same or different and represent a halogen atom,

R ⁵ is a hydrogen atom; d-4 alkyl optionally substituted by a halogen atom; or C 4 alkyl (this alkyl may be substituted by a halogen atom) or d-4 alkoxy (this alkyl moiety May be substituted with a halogen atom.) The compound according to claim 1, which represents phenyl optionally substituted with:

6. R ¹ and R ² represent a hydrogen atom, R ³ and R ⁴ represent a halogen atom, R ⁵ represents unsubstituted C 4 alkyl, R ⁶ represents phenyl, and the phenyl is mouth Gen atoms (which may be the same or different); Shiano; nitro; halogen which may be more substituted atom d ₄ alkyl; or 1 one by a C I ₄ alkoxy optionally substituted by halogen atom, 2 The compound according to claim 1, wherein —, or 3-— is substituted, and R ⁷ represents a hydrogen atom or an alkyl substituted by d-4 alkoxy.

7. A pesticidal composition comprising the compound according to any one of claims 1 to 6, or a salt or solvate thereof.

8. The pesticide according to claim 7, wherein the pesticide is used as an insecticide, a pesticide, an acaricide, a fungicide, a fungicide, a herbicide, or a herbicide.

9. A method for controlling pests, comprising treating an area to be protected from pests with an effective amount of a compound according to any one of claims 1 to 6 or a salt or solvate thereof. .

10. The pests are lepidopteran, Hemiptera, Coleoptera, Acarina, and A phytopathogenic fungus selected from Pests selected from Pests of Diptera, Rice Blast Fungus, Rice Sheath Blight Fungus, Cucumber Blight Fungus, Cucumber Blight Fungus, Cucumber Powdery Mildew Fungus, and Wheat Leaf Rust Fungus; The control method according to claim 9, which is a harmful plant selected from the group consisting of A. sylvestris, A. sylvestris, A. americana and A. americana.

11. Use of the compound according to any one of claims 1 to 6 or a salt or solvate thereof for the production of a pesticidal agent.