WO1995033730A1 - Imidazole derivative, production process, and herbicide - Google Patents

Abstract

An imidazole derivative represented by general formula (I) and excellent in herbicidal activity when used, in particular, for soil treatment, wherein X represents phenyl which may be substituted by halogen, optionally substituted C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, nitro, cyano, C1-C6 alkoxycarbonyl or other substituent(s), pyridyl which may be substituted, etc.; one of Y and Z represents C1-C6 haloalkyl and the other represents hydrogen, halogen, C1-C6 alkyl, etc.; and R represents C1-C6 alkyl which may be substituted by optionally substituted C1-C6 alkoxy, optionally substituted C3-C6 alkenyloxy, optionally substituted C3-C6 alkynyloxy, optionally substituted aralkyloxy, etc.

Description

 Description Dimidazole derivatives, manufacturing methods and herbicides Technical field:

 The present invention relates to a novel imidazole derivative useful as a herbicide and a method for producing the same. Background art:

 In the cultivation of agricultural and horticultural crops, many herbicides are used for weed control. However, there is a need for the development of drugs that can be used more safely and safely at lower doses because they cause harm to crops, remain in the environment, and pollute the environment.

 The following are disclosed as compounds similar to the compound of the present invention.

 (l) USP. 4, 314, 844 describes the herbicidal activity of imidazole derivatives and the method for producing them. However, there is no specific description of the compound according to the present invention. Further, compounds in which R is a hydrogen atom or an ethoxycarbonyl group in the general formula [I] described below have been synthesized, but their herbicidal activity is insufficient.

 (2) Also, EP-0 283 173 describes that certain imidazole derivatives are useful as insecticides and nematicides. However, it does not specifically disclose the compound relating to the present invention, nor does it disclose any usefulness as a herbicide.

 The purpose of the present invention is to provide a herbicide that can be synthesized industrially advantageously, is effective at a lower dose, has high safety, and has high crop selectivity. Disclosure of the invention:

The present invention relates to an imidazole derivative represented by the general formula [I], a production method and a herbicide. You.

Wherein [I], X is [halogen atom, (halogen atom, an optionally substituted Hue alkenyl group, C - _e alkoxy group, _d-6 alkoxycarbonyl group, Horumiruokishi group or Shiano group!) Substituted with also a C alkyl group, (halogen atom, an optionally substituted Fuweniru group, alkoxy group, C alkoxycarbonyl group or Shiano group) may be substituted with C, - _e alkoxy group, d-alkylthio group, C haloalkylthio group, ₆ alkylsulfide alkylsulfonyl groups, C] - alkyl sulfonyl groups, C Nono b alkylsulfonyl groups, C _l-6 alkylsulfonyl O carboxymethyl groups, C ₃ - ₆ cycloalkyl groups, C ₃ - ₆ Arukeniruokishi group, C ₃ - ₆ Arukini Ruokishi group, C ₃ - ₆ alkenylthio group, C ₃ - _e alkynylthio, nitro group, Ji Sairyoku Rubamoiru group, a sulfamoyl group, Cal Hexyl group, formyl group, Shiano group

, C alkoxycarbonyl group, an optionally substituted C Bok ₆ alkyl group with halogen, mono Moshiku (C, - - ₆ alkyl group, C! ₆ Ashiru group is properly alkoxy carbonyl group) depending disubstituted amino group, an optionally substituted phenyl group, an optionally substituted Fuwenokishi group or an optionally substituted pyridinium Jiruoki sheet group] which may be substituted with Fuweniru group, (halogen atom, C, - _e alkyl group, Pyridyl group, pyridyl N-oxide group, alkyl group, halogen atom or oxo group) which may be substituted with 1 to 3 haloalkyl groups, alkoxy groups or cyano groups). N, 0, or 5-6 membered the heterocyclic fused ring group of benzene containing S, (halogen atom, C, - _e alkyl or d haloalkyl group) which may be substituted with thienyl group Represents a furyl group which may be substituted by (halogen atom, d- ₆ alkyl group or C i- _e haloalkyl group) or an aralkyl group which may be substituted by (halogen atom or d- ₆ haloalkyl group) .

Y, Z has one represents a ₆ haloalkyl group, the other is a hydrogen atom, halogen atom, C -! ₆ alkyl group, a haloalkyl group, ₆ alkylthio groups, C 1 -6 alkoxy group, Shiano group, a formyl group, human Dorokishii Mi Bruno methyl group, C 1 -6 Arukokishii Mi Nomechiru group, C -! ₆ alkoxycarbonyl group, (was a halogen atom or C _i-6 alkyl group) in optionally substituted Fuweniru group which may be substituted by a halogen atom Benzoiru group, C - to Table ₆ alkylcarbonyl group or a carboxy group!.

R represents [(halogen atom, C, —S alkoxy group, ds alkoxyalkoxy group, optionally substituted phenyl group, optionally substituted phenoxy group, C, -6 alkoxycarbonyl group, C ₃ - ₆ cycloalkyl group or Shiano group) which may be substituted with an alkoxy group, is substituted with (halogen, C -e alkoxy groups, unsubstituted or good I Fuweniru group, an alkoxycarbonyl group, or Shiano group)! good C ₃ be - 6 Arukeniruokishi group, (halogen atom, C _i-6 alkoxy group, an optionally substituted Fuweniru group, d-6 alkoxycarbonyl or Shiano group) C ₃ which may be substituted by - e Arukiniruokishi group, (halogen atom, an alkoxy group, an optionally substituted Fuweniru group, C _i-6 alkoxycarbonyl group or Shiano group) may be substituted with Ararukiru Alkoxy group, _d-6 alkylcarbonyl O alkoxy group, (halogen atom, C -! ₆ alkoxy group, an optionally substituted Fuweniru group, - G alkoxycarbonyl or Shiano group) C I ₆ may be substituted by alkylthio O group, alkylsulfinyl group, an alkylsulfonyl group, an Fuwenokishi group optionally substituted by a halogen atom, C _i-6 alkyl group, § Mi substituted by (C iS alkyl group may properly C ₆ alkoxycarbonyl group) It represents an ₈ alkenyl group - amino group, d - ₆ alkoxy force which may Fuweniru group or a C I is substituted with alkyl groups Lupo alkylsulfonyl group] optionally C _i-6 alkyl group or optionally substituted by a C _3.

 In the above formula [I], examples of the substituent for the phenyl-alkyl-phenyl group and the phenyl-alkoxy-phenyl group of X include a halogen atom, c

, -6 haloalkyl groups and the like.

Examples of the substituent for X's biphenyl group, phenoxyphenyl group and pyridyloxyphenyl group include a halogen atom and d-6 haloalkyl group. Examples of the condensed ring group of benzene and a 5- to 6-membered hetero ring containing 1 to 3 N, 0 or S of X include a condensed ring group of a heterocyclic ring and a phenyl group as shown below. And

. '

Ν.

キノ リル基などのベンゼンと ピリ ジル基の縮合環基等が挙げられる。

Examples include a fused ring group of benzene and a pyridyl group such as a quinolyl group.

 In the present invention, when the phenyl group, heterocycle or pyridyl group of X is substituted with two or more substituents, these substituents may be the same or different.

 (Production of compounds)

 The compound of the present invention can be produced by the following method.

Manufacturing method (1)

X

 Η R β

(I) [I-11] [I-12] In the formula, X, Υ, Z and R have the same meanings as described above, and L represents a leaving group. Also, as the leaving group L, chlorine, a halogen atom such as bromine, 0 S 0 ₂ r (r is 6 alkyl group such as a methyl group, an optionally substituted Fuweniru groups such as p- Bok lil group And so on). In this production method, compound (II) and compound (ΠΙ) are mixed in an inert solvent at a temperature of 10 ° C. to 200 ° C. in the presence of a base for several minutes to several 10 The reaction ratio in which the reaction is carried out for a time is preferably 1 equivalent of the compound (II), 1 to 5 equivalents of the compound (III) and 1 to 5 equivalents of a base.

 In this reaction, one or both of the compounds [1-1] and [1-2] are obtained depending on the type of the substituent.

 Solvents that can be used in the reaction include hydrocarbons such as hexane, heptane, benzene, toluene, and xylene; ethers such as THF, dioxane, and getyl ether; methanol, ethanol, and propanol. Alcohols, amides such as DMF and DMS O, halogenated solvents such as chloroform, dichloromethane, carbon tetrachloride, and dichloroethane; esters and esters such as ethyl acetate, methyl acetate, and propyl acetate. Cetonitrile and the like.

 Examples of the base used in the reaction include aliphatic amines such as triethylamine, getylisopropylamine and piperidine, aromatic amines such as pyridine and aniline, and sodium carbonate. Alkali metal carbonates, such as calcium carbonate, calcium carbonate, etc., metal alkoxides, such as calcium methoxide, sodium ethoxide, magnesium ethoxide, calcium tert-butoxide, etc. Al metal hydroxides such as tritium and hydroxide hydroxide, metal hydrides such as sodium hydride and the like can be mentioned.

 The compound (II) can be synthesized, for example, according to the production method described in U.S.P. 4,314,844. Manufacturing method (2)

In the compound (I), Y is a haloalkyl group, Z is a chlorine atom, a fluorine atom, a substituted benzoyl group, a cyano group, a formyl group, a hydroxyiminomethyl group, an alkoxyminomethyl group, and an alkoxyl group. Those having a carbonyl group, a trifluoromethyl group, an alkylthio group or a carboxy group can be produced by the following method.

One six V

式中、 X, Y, R, Lは前記と同じ意味を表わし、 Vはヨウ素原子又は臭素原 子を表わし、 R¹ , R² , R⁴ , R⁵ は ₆ のアルキル基を表わし、 R³ は水 素原子又は d- ₆ のアルキル基を表わし、 R⁶ はハロゲン原子を表す。 また、 n は 0— 5の整数を表す。

In the formula, X, Y, R, and L have the same meanings as described above, V represents an iodine atom or a bromine atom, R ¹ , R ² , R ⁴ , and R ⁵ represent an alkyl group of ₆ , R ³ Represents a hydrogen atom or a d- ₆ alkyl group, and R ⁶ represents a halogen atom. N represents an integer of 0-5.

Manufacturing method (3)

 The compound of the present invention can also be obtained by the following production method.

製造方法 （ 4 )

Manufacturing method (4)

Among the compounds [I], the compound [Π], which is a starting material of a compound in which Y is a CF ₃ group and Z is a C! -S alkyl group, can be produced by the following method.

Manufacturing method (5)

In the compound [I] of the present invention, a compound in which Y is a CF ₃ group and Z is a substituted phenyl group can be produced by the following method.

(Wherein, X and R have the same meanings as described above, and Z represents a de-alkyl group.)

Further, in the compound of the present invention [I], when Y is a haloalkyl group and Z is an alkylcarbonyl compound, the compound wherein Z is an alkyl group is oxidized. Can be manufactured

(In the formula, X represents the same meaning as described above, Y represents a C ₆ haloalkyl group, and R ⁷ represents

C: represents a -5 alkyl group. BEST MODE FOR CARRYING OUT THE INVENTION

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

 (Example 1)

 5 _Bromo _2-(4-chlorophenyl) 1-1 -ethoxymethyl-14 -trifluoromethylimidazole (Compound No.1) and 4 _bromo_2-(4 -chlorophenyl)-1 -ethoxymethyl_5 — Synthesis of Trifluoromethylimidazole (Compound No. 2)

 1 2

4 (5) — Promo 2 — (4 monophenyl phenyl) 1 5 (4) — Trifluoromethilymidazole (1.26 g, 3.9 mm 01) is converted to THF (40 m 1 Dissolved in) Then, potassium t-butoxide (0.56 g, 5.0 mmol) was added, and the mixture was stirred for 10 minutes. 0.48 g (5.1 mmol) of chloromethyl ethyl ether was added dropwise at room temperature, and the mixture was further stirred for 3 hours after completion of the addition. The reaction solution is poured into water, extracted with ethyl acetate, dehydrated, and concentrated under reduced pressure. The obtained residue is subjected to silica gel column chromatography (developing solvent hexane ZA c 0 E t = 20/1). Compound 1 (1.03 g, 69%, m.p 86-87 ° C) and Compound 2 (0.16 g, 11%, m ρ 73-74) ° C). The structures of Compound 1 and Compound 1 were determined by two-dimensional NMR spectral analysis. That is, in the two-dimensional NMR spectrum, in the case of compound 2, a force coupling is observed between the carbon adjacent to the trifluoromethyl group and the CH ₂ OEt proton of the ethoxymethyl group. , in the case of compound 1, KoTsuta structure determination by mosquito Tsupuri ring was observed between the pro tons of carbon atoms and CH ₂ 0 E t adjacent to a bromine atom.

(Example 2)

 Synthesis of 4,5_Bis (trifluoromethyl) 1-2— (4—chlorophenyl) -1-ethoxymethylimidazole (Compound No. 63)

F, C

63 2 — (4 — chlorophenyl) 1 — 1-ethoxymethyl-5 — chloride 4 — trifluoromethylimidazole (Compound No. 9) 1.40 g (3.25 mm 0 1), iodide Trifluoromethyl (6.4 g, 32.7 mm 01), copper powder (2.39 g), and DMF (8 ml) were charged into an autoclave and heated at 130 ° C for 13 hours. After adding a cerium to the reaction solution and filtering, 2 O ml of benzene and 2 O ml of ethyl acetate were added. After washing with water, the organic layer is dehydrated and concentrated. The resulting residue is purified by silica gel chromatography, and 2 — (4 — chlorophenyl) — 4, 5 — bis (trifluoromethyl) imidazole 0.5 g was obtained.

 Ή-NMR (CDCls) <5 p pm: 7.44 (2H, d), 7.85 (2H, d)

 M S / z: 3 1 4

 Using this as a starting material, a compound of the compound No. 63 (0.4 g) was obtained in the same manner as in Example 1. m.p 5 4 — 5 6 ° C

(Example 3)

 2- (4-chlorophenyl) -1-5-n-propoxymethyl-14-trifluoromethylimidazole (Compound No. 236) and 2— (4-chlorophenyl) -14-methyl-1- Synthesis of n —propoxymethyl _ 5 — trifluoromethylimidazole (Compound No. 237)

酢酸ナ ト リ ウム 1. 1 7 g ( 1 4. 3 mm o l ) を水 3. 5 m l に溶解し、 これに攪拌下、 3， 3—ジブロモ一 1 , 1， 1 — ト リ フルオロー 2—ブタノ ン 2. 0 8 g ( 7. 3 mm 0 1 ) を加え、 7 0— 8 0 で 1 5分加熱した。 室温ま で冷却したのち、 4—クロ口べンズアルデヒ ド 0. 9 8 g ( 7. O mm o l ) をメ タノール 2 5 m l に溶解した液を一気に加え、 さ らに濃ァンモニァ水 7 m 1 を室温で滴下した。 反応液が 2層に分離したため T H F 7 m 1 を加え均一溶液に し、 終夜攪拌した。 反応混合物を減圧下濃縮し、 残留物に水と酢酸ェチルを加え 、 分液し、 有機層を脱水したのち、 濃縮して得られた残差をシリ 力ゲルクロマ ト グラフィ 一にて精製することにより、 2— （ 4 —クロロフヱニル） 一 4—メチル — 5 _ ト リ フルォロメチルイ ミ ダゾ一ル 0. 3 7 gを得た （収率 4 0 % ) 。 このものを出発原料と して、 実施例 1 と同様の方法により化合物番号 2 3 6の 化合物 0. 4 3 g (収率 4 6 %) と化合物番号 2 3 7の化合物 0. 3 8 g (収率 4 1 % ) を得た。

1.17 g (14.3 mmol) of sodium acetate was dissolved in 3.5 ml of water, and 3,3-dibromo-1,1,1,1—trifluoro-2- 2.08 g (7.3 mm 01) of butanone was added, and the mixture was heated at 70 to 80 for 15 minutes. After cooling to room temperature, a solution prepared by dissolving 0.98 g (7.0 mmol) of 4-chlorobenzaldehyde in 25 ml of methanol was added at once, and 7 ml of concentrated ammonia water was further added. It was added dropwise at room temperature. Since the reaction solution was separated into two layers, 7 ml of THF was added to make a homogeneous solution, and the mixture was stirred overnight. The reaction mixture is concentrated under reduced pressure, water and ethyl acetate are added to the residue, liquids are separated, the organic layer is dehydrated, and the residue obtained by concentration is purified by silica gel chromatography. 0.37 g of 2-, (4-chlorophenyl) -1-methyl-5-trifluoromethylimidazole was obtained (yield: 40%). Using this as a starting material, 0.43 g of compound No. 236 (yield 46%) and 0.38 g of compound No. 237 in the same manner as in Example 1 were prepared. Yield 41%).

Representative examples included in the present invention, including the above examples, are summarized in Table 1 below. table 1

 Compound

 No.X Y Z R Physical constant

50

表 1 (つづき）

Table 1 (continued)

Compound

1 (つづき） XY ζ R Physical constant

1 (continued)

Compound

 X Y ζ R Physical constant

CF ₃ Br CH ₂ 0Et

1 (つづき） 30 C0 ₂ CH ₃ CF ₃ Br CHoOEt 97-100. C

1 (continued)

Compound

No.X Y Z R Physical constant 127-128 ° C

3 96—99 ° C

1 (つづき）

1 (continued)

Compound

No.X Y Z R Physical constant e

1 (つづき）

1 (continued)

Compound §

No.X Y Z R Physical constant

71

1 (つづき）

1 (continued)

Compound

 X Y ζ R Physical constant

1 (つづき） 50

1 (continued)

Compound

No.X Y Z R Physical constant n 1.5641

n 1.4935 n 1.5277

n 1.4935

1 (つづき） 82—83 ° C

1 (continued)

Compound

Number X Y Z R Physical constant n 1.4781 n 1.4693 n 1.4775

1 (つづき） 83- 84 ° C n 1.5295 nn '1.4948 92-93 ° C

1 (continued)

Compound

No.X Y Z R Physical constant

C

98 OV i CF ₃ Br CH ₂₀ CH. CH ₂ CH ₂ C1 72-73 ° C

99 3-84 ° C

100 6-47 ° C

101 1.5328

1 (つづき） 102 3-44 ° C

1 (continued)

Compound

No.X Y Z R Physical constant

103 1.4675

104 1.4695

105 1.4682

106 116 ° C

107 OVci Br CF ₃ CH ₂ 0CH ₂ C≡C-CH ₃ 81—82 ° C

108

 109

110 6

111 2

1 (つづき） 112 9

1 (continued)

Compound

No.X Y Z R Physical constant n 1.5253 n 1.5249

67- 69 ° C

106-108 ° C

CF, Br CH ₂ oOuC ₃ HJ, 76-78 ° C

Br CF ₃ CH ₂ 0C ₃ H ₇ ⁿ 83-85 ° C

119 79 ° C

120 1.5267

121 76 ° C

1 (つづき） 122 1.5553

1 (continued)

Compound

 X Y Ζ R Physical constant

123-83 ° C

124 1.5157

125 1.5146

126 — 120 ° C

127 1.5026

128 1.5027

129 66. C

130 52 ° C

131 1.4668

1 (つづき） 132 65 ° C

1 (continued)

Compound

w ゥ XY ζ R Physical constant 20 82 22 88 53 420 680

142 〇 ~ Cl Br CF ₃ CHj n 1.5689 1 (continued)

Compound

No.X Y Z R Physical constant

 CI

151 CN Br CF ₃ CH ₂ 0C ₃ H ₇ ⁿ 78- 79 ° C 1 (continued)

Compound

No.X Y Z R Physical constant C

CH ₃

155 CI Br CF ₃ CH0C ₂ H ₅ glassy

 CH

 20.3

156-<CI Br CHC0 ₂ C ₂ H ₅ n 1.4918

0C ₂ H ₅

157 OVci CF Br CHgOCOC H, 83-84 ° C

H ₅ C ₂ 0,

158-OV ^cl CF ₃ Br CH ₂ 0C ₃ H n 1.5305

159 CI Br CF ₃ CH ₂ 0C ₃ H ₇ ^: 62-64 ° C

_{160 CH 3 CF 3 Br CH 29} 0uC les _{s 3} Hn ₇ 49- 50 ° C 1 (continued)

Compound

XY ζ R Physical constant

170 CH ₂ CI CF ₃ Br CH ₂ 0C ₃ H ₇ ⁿ n 1.5192 1 (continued)

Compound

No.X Y Z R Physical constant

1 (つづき）

1 (continued)

Compound

No.X Y Z R Physical constant

19.3

185 OVCF _: Br CH CH2 OCQ Ηγ n 1.5173

 D

186 69 ° C

187 51. C

188 1.5451

189 53 ° C

1 (つづき） 190 49 ° C

1 (continued)

Compound

w X Y ζ R Physical constant

191 1.5361

192 ° C

193

194 1.5224

 CH

 20.5

195 OVCH, Br CF ₃ CH ₂ 0C ₃ H ₇ n 1.5268

n 190—191 ° C

1 (つづき）

1 (continued)

Compound

No.X Y Z R Physical constant n 1.5242

119- 120 ° C

56- 58 ° C

63-64. C

n 92— 93 ° C

表 1 (つづき） :

Table 1 (continued)

Compound

No.X Y Z R Physical constant

98 ° C

168 ° C

 24. 0

220 CF ₃ Br CH ₂ 0C, H ₇ ⁿ n 1.5533

• S ^xヽ CI 1 (continued)

Compound

No.X Y Z R Physical constant

1 (つづき）

1 (continued)

Compound

No.XYZR Physical constant

232 CH ₂ 0CH CF ₃ Br CH OC ₃ H ₇ ^: n 1.5378

233 Br CH2 OC9 Hj n 1.5891

234 Br CF _; CH2 OC3 H'j n 1.5881

235 Br CF _; CH OC3 Hj n '1.5809

236 CF ₃ CH ₃ CH ₂ 0C, H ₇ '61-62 ° C

237 CI CH ₃ CF ₃ CH ₂ 0C ₃ H ₇ ^: n 1.5106

238 CF ₃ Br CH ₂ 0C ₂ H ₇ n 1.5378

C0 ₂ CH ₂ 0C ₃ H ₇ ⁿ

ε,£ε/6 OAV一 239 CF ₃ Br CH, 0C ₃ H 36-37 ° C

ε, £ ε / 6 OAV one

Ρ

Ρ Ρ

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a OSト 8 H^e30S^zH3 jo Z9Z

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a 26-68 ^e H30 ³ H30 ^s H3 Jg ^ε ί13 ^G dO 092

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6fnO / S6dT / X3J οε, εε / 56 OAV One 0 ー-

( ^ω ΉΕ) 8Ζ 'I'(s' U) Z / "S ΉΖ ΉΖ) 63 Έ '(m'H2) 99' (1 Ή £) Ζ6 Ό

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(s' HI) 9 '丄' (s'HZUS'S '(1 ·} \ Ζ) 2Ζ Έ' («ι ΉΖ) 05 'ΐ' Ή8) 98" 0

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-(Ρ Ήΐ) Ζ6 Ί '(Ρ' HT) 9S 'ί' (s'HZUI 'S

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 *

(Ρ'Ηΐ) 6 '' (P'HI) S 丄 '(s' HZ)' 9 '(?' H2) 2C * S '("i'HZ) TS'I Ό' HS) 98 Ό ε 氺

(P Ήΐ) ΐ0 -L '(P' HIU 9 '(s'H2) SS'S Ό' HS) 0G '(m' HS) S9 'ΐ' (1 Ήδ) 06 Ό

 Z *

(s 'Ηΐ)' 8

(Ρ 'Ηΐ) 96 丄 丄' (Ρ 'Ηΐ) Ζ6' 丄 '(s' HZ) SS '9' (1 'Η2) 09Έ' (ω'ΗΖ) Ζ9ΐ '') 2) 06 Ό ΐ *

[: Ui d cl 9 ( ^ε ΐ 3 α 3) — one '— Η []

^Α Η ^ε 30¾3 3 丄 9Ζ

0 € L ££ / S6 OA. ΐ f

'HZ) 9C' 8 '(Ρ ΉΖ) 08 Ά' (s' HZ) 6 'S' 0 'H2) ZS'S' ('ΗΖ) ^' ΐ Ό Ή £) ^ 8 "0

[: Ui ddg ( ⁹ ρ-0 SO) — one Η,)

 8 *

(s Ήΐ) 9 ^ "A '(s' H2) S ^ -g' (ϊ ΉΖ) 09 'S' (Η2) 99Ι 'G' HS) 6.0

L * βη \ os6df / iDJ οεζ.εε / 56 OAV The compound of the present invention shows high efficacy against various field weeds such as mexican grass, Aquinoeno cologsa and Inubu by any of soil treatment and foliage treatment under upland cropping conditions, and particularly shows excellent efficacy in upland soil treatment. . The compounds of the present invention include compounds having selectivity for crops such as corn, wheat, and soybeans.

 The compound of the present invention has excellent herbicidal activity against weeds such as paddy field weeds such as Nobie, Tamagayari, Omodaka and Firefly, and also includes compounds showing selectivity to rice. The compounds of the present invention can also be applied to the control of weeds in orchards, lawns, track ends, vacant lots and the like.

 Furthermore, the compounds of the present invention include those having a plant growth regulating action, a bactericidal activity, and an insecticidal / miticidal activity.

(Herbicide)

 The herbicide of the present invention contains one or more of the compounds of the present invention as an active ingredient. When the compound of the present invention is actually applied, it can be used in a pure form without adding other components, and can be in the form of a general pesticide for use as a pesticide, that is, a wettable powder, a granule, It can also be used in the form of powders, emulsions, aqueous solvents, suspensions, flowables and the like. When solid additives are used as additives and carriers, plant-based powders such as soy flour and flour, diatomaceous earth, apatite, gypsum, talc, bentonite, pyrophyllite, clay, etc. Organic and inorganic compounds such as fine powder, sodium benzoate, urea and sodium sulfate are used. For liquid dosage forms, petroleum fractions such as kerosene, xylene and sorbent naphtha, cyclohexane, cyclohexanone, dimethylformamide, dimethylsulfoxide, alcohol, acetate , Trichloroethylene, methyl isoptil ketone, mineral oil, vegetable oil, water, etc. are used as solvents. Surfactants can be added, if necessary, to obtain a uniform and stable form in these preparations.

The concentration of the active ingredient in the herbicide of the present invention varies depending on the form of the preparation described above. For example, in the case of a wettable powder, it is 5 to 90%, preferably 10 to 8%. 5%: 3 to 70% in emulsion, preferably 5 to 30%: 0.01 to 30% in granules, preferably 0.05 to 5% A concentration of 10% is used. The wettable powder and emulsion thus obtained are diluted to a predetermined concentration with water to form a suspension or emulsion, and the granules are sprayed on the soil before or after germination of the weeds. Or it is mixed. In applying the herbicide of the present invention, an appropriate amount of 0.1 g or more of the active ingredient is applied per 10 ares.

 Further, the herbicide of the present invention can be used by mixing with known fungicides, insecticides, acaricides, herbicides, plant growth regulators, fertilizers and the like. In particular, it is possible to reduce the amount of drug used by mixing and using herbicides. In addition to the labor saving, the synergistic action of the mixed drug can be expected to have a higher effect. In that case, a combination with a plurality of known herbicides is also possible.

 Examples of agents that can be used in combination with the herbicide of the present invention include carbamate herbicides such as benthiocarb, molinate, and dime pipelet; tiocarbamate herbicides; butachlor; pretilachlor; Acid amide herbicides, such as chlormethoxinil, biphenox, etc .; triazine herbicides, such as atrazine and dianadine; sulfonylurea herbicides, such as chlorsulfuron and sulfometuron-methyl. Carboxylic herbicides such as MCP and MCPB, dinitroaniline herbicides such as trifluralin and benzimetalin, urea herbicides such as linuron and diuron, and diclohop-methyl. Phenoxy phenoxypropionic herbicide, flazifop Pyridyloxyphenoxypropionic acid herbicides such as tyl, benzoylaminopropionic acid herbicides such as benzoylprophetyl and franpropethyl, imazaquin imidazolinone herbicides, and others And cyclohexanedione herbicides such as pilophos, Daimlon, Benyuzon, difenzocoat, nabroanilide, etobenzanide, triazovanamide, kink mouth rack, and cetoxidim, cresodim. And the like. Vegetable oils and oil concentrates can also be added to these combinations.

〔Example〕

 (Herbicide)

Next, some formulation examples of the herbicide of the present invention are shown. The addition ratio and addition ratio can be changed in a wide range without being limited to the present embodiment. Parts in Formulation Examples are parts by weight.

Example 4 wettable powder

 Compound of the present invention 20 parts

 White carbon 20 parts

 Diatomaceous earth 5 2 parts

 Sodium alkyl sulfate 8 parts

 The above components were uniformly mixed and finely pulverized to obtain a wettable powder containing 20% of the active ingredient.

Example 5 Emulsion

 Compound of the present invention 20 parts

 Xylene 5 5 parts

 Dimethylformamide 1 5 parts

 Polyoxyethylene fuel 10 parts

 The above ingredients were mixed and dissolved to obtain an emulsion containing 20% of the active ingredient.

Example 6 granules

 5 parts of the compound of the present invention

 Talc 40 parts

 Cray 3 8 copies

 Bentonite 10 copies

 Sodium alkyl sulfate 7 parts

 The above components were uniformly mixed and finely pulverized, and then granulated into particles having a diameter of 0.5 to 1.0 mm to obtain granules having an active ingredient of 5%. Next, test examples relating to the effect of the herbicide of the present invention will be shown.

 The herbicidal effect was investigated according to the following criteria and expressed as a herbicidal index.

Survey criteria

 Killing rate killing index

 0% 0

20 to 29% 2 4 0 to 4 9% 4

 6 0-6 9% 6

 8 0-8 9% 8

 1 0 0% 1 0

 Numerical values of 1, 3, 5, 7, and 9 indicate intermediate values between 0 and 2, 2 and 4, 4 and 6, 6 and 8, and 8 and 10, respectively.

 (Green weight of above-ground part in untreated area-Raw weight of above-ground part in treated area) Herbicidal rate (%) = X100

Test example 1 Upland soil treatment

A plastic pot having a surface area of 250 cm ² was filled with field soil, and seeds of Meechishiba, Aquinoeno coroda and Inubu were sown, and a 0.5 cm cover soil was placed thereon. The following day, a predetermined amount of the diluent of the wettable powder shown in Example 4 was evenly sprayed on the soil surface. Twenty days after the treatment, the herbicidal effect was investigated. The results are shown in Table 2.

Industrial applicability:

As described above, the imidazole derivative compound of the present invention represented by the formula [I] was shown to have excellent herbicidal activity in a soil treatment test. Therefore, the compound of the present invention is useful as a herbicide.

Table 2 Compounds Active ingredients

Number g / 10 a 'キ キ キ キ

1 1 0 0 1 0 1 0 1 0

3 1 0 0 1 0 1 0 1 0

4 1 0 0 1 0 1 0 1 0

5 1 0 0 1 0 1 0 1 0

8 1 0 0 1 0 1 0 1 0

19 1 0 0 1 0 1 0 1 0

40 1 0 0 1 0 1 0 1 0

41 1 0 0 1 0 1 0 1 0

48 1 0 0 1 0 1 0 1 0

53 1 0 0 1 0 1 0 1 0

54 1 0 0 1 0 1 0 1 0

67 1 0 0 1 0 1 0 1 0

68 1 0 0 1 0 1 0 1 0

74 1 0 0 1 0 1 0 1 0

82 1 0 0 1 0 1 0 1 0

83 1 0 0 1 0 1 0 1 0

93 1 0 0 1 0 1 0 1 0

94 1 0 0 1 0 1 0 1 0

96 1 0 0 1 0 1 0 1 0

98 1 0 0 1 0 1 0 1 0

100 1 0 0 1 0 1 0 1 0

102 1 0 0 1 0 1 0 1 0

108 1 0 0 1 0 1 0 1 0

109 1 0 0 1 0 1 0 1 0

110 1 0 0 1 0 1 0 1 0

121 1 0 0 1 0 1 0 1 0.

122 1 0 0 1 0 1 0 1 0

123 1 0 0 1 0 1 0 1 0 Table 2 (continued) ィ 匕 物 Active ingredient 早 early index

 ,, A

¾- g / l O

126 1 0 0 1 0 1 0 1 0

127 l 0 0 l 0 丄 0 1 0

128 丄 0 0 丄 0 1 0 1 0

 1

 132 1 υ υ 1 υ 1 U 1 0

133 1 0 ϋ 1 υ 1 U 1

 1 0 0 1 0 丄 0 1 丄 υ

Ι ό ΐ 1 0 0 1 0 I 0 丄 υ

138 1 0 0 1 0 I 0 1 υ

139 1 0 0 1 0 1 0 I 0

143 1 0 0 1 0 1 0 I 0

144 1 0 0 1 0 1 0 I 0

145 1 0 0 1 0 1 0 I 0

147 1 0 0 1 0 1 0 1 0

149 1 0 0 1 0 1 0 1 0

150 1 0 0 1 0 1 0 1 0

152 1 0 0 1 0 1 0 1 0

160 1 0 0 1 0 1 0 1 0

162 1 0 0 1 0 1 0 1 0

163 1 0 0 1 0 1 0 1 0

164 1 0 0 1 0 1 0 1 0

171 1 0 0 1 0 1 0 I 0

172 1 0 0 1 0 1 0 I 0

182 1 0 0 1 0 1 0 1 0

192 1 0 0 1 0 1 0 1 0

194 1 0 0 1 0 1 0 1 0

214 1 0 0 1 0 1 0 1 0

Table 2 (continued) Compound Active ingredient Herbicidal index

 Mouth

 -g / 10 a シ キ キ キ

215 1 0 0 1 0 1 0 1 0 220 1 0 0 1 0 1 0 1 0 222 1 0 0 1 0 1 0 1 0 236 1 0 0 1 0 1 0 1 0 239 1 0 0 1 0 1 0 1 0 240 1 0 0 1 0 1 0 1 0 250 1 0 0 1 0 1 0 1 0 254 1 0 0 1 0 1 0 1 0

1 0 0

¾ 合 合 1 0 0

 Comparative compound A

 Comparative compound B

Claims

The scope of the claims 'Imidazole derivative represented by general formula (I) _t

{In the formula, X, [halogen atom, (halogen atom, an optionally substituted Fuweniru group C alkoxy group, d alkoxycarbonyl group, formyl Ruokishi group or Shiano group) with an optionally substituted C Bok ₆ alkyl group, (halogen atom, an optionally substituted phenyl group, C -! alkoxy groups, C i alkoxycarbonyl group or chopsticks Anomoto) which may be substituted with C alkoxy group, d ₆ alkylthio group, C, - Roarukiruchio group , C alkylsulfide alkylsulfonyl group, C alkylsulfonyl group, C -! ₆ alkylsulfonyl group, C alkylsulfonyl O carboxymethyl group C cycloalkyl group, C ₃ - ₆ Arukeniruokishi group, C ₃ - ₆ Arukiniruoki sheet group, C ₃ - ₆ alkenylthio group, C ₃ - ₆ alkynylthio, nitro group, Chiokaru Bamoiru group, a sulfamoyl group, a carboxyl group, a formyl group Amino or di-substituted by a cyano group, a C! -Alkoxycarbonyl group, a C alkylcarbonyl group, an alkyl group, an acyl group or a C alkoxycarbonyl group optionally substituted by halogen) Group, phenyl group which may be substituted, phenyl group which may be substituted, phenyl group which may be substituted or pyridyloxy group which may be substituted] (halogen atom, alkyl group, haloalkyl group, d alkoxy group) Or a pyridyl group optionally substituted with a cyano group), an alkyl group, a halogen atom or an oxo group which may be substituted with 13) N, 0 or S 56 Condensed ring group of a membered hetero ring and benzene, a phenyl group which may be substituted with (halogen atom, d alkyl group or C haloalkyl group), Androgenic atom, an alkyl group or _d-6 haloalkyl group) which may be substituted disadvantageous group or (a halogen atom or a C i-haloalkyl group) may be substituted with Ararukiru group. Y, Z has one is C i - represents a ₆ haloalkyl group and the other is a hydrogen atom, a halo gen atom, d alkyl group, a haloalkyl group, ₆ alkylthio groups, C alkoxy group, Shiano group, formyl group, human Droxyiminomethyl group, C alkoxyiminomethyl group, alkoxycarbonyl group, phenyl group optionally substituted with (halogen atom or dalkyl group), benzoyl group optionally substituted with halogen atom, alkylcarbonyl Represents a group or a carboxyl group. R is [(halogen atom, alkoxy groups, C -! ₆ alkoxy one Ryo alkoxy group, an optionally substituted Fuweniru group, an optionally substituted Fuwenokishi groups, C alkoxycarbonyl groups, C cycloalkyl group or Shiano group) A C ₃ -alkenyloxy group which may be substituted by a C alkoxy group which may be substituted by (halogen atom, Ci- ₆ alkoxy group, an optionally substituted phenyl group, an alkoxycarbonyl group or a cyano group) , (halogen atom, an alkoxy group, an optionally substituted Fuweniru group, d-alkoxycarbonyl group or Shiano group) may be substituted with C ₃ - ₆ Arukiniruokishi group, (halogen atom, § alkoxy group, substituted which may be phenyl group, C i - ₆ alkoxycarbonyl or optionally substituted Ararukiruokishi group Shiano group), Rukirukarubo two Ruokishi group, (halogen atom, ₆ alkoxy group, an optionally substituted Fuweniru group, C alkoxycarbonyl group or Shiano group) a C be substituted with, _-6 alkylthio groups, C 4 alkylsulfinyl group, C alkyl sulfonyl group, optionally Fuwenokishi group optionally substituted by a halogen atom, C] - ₆ alkyl carbonylation Le group, (C i - alkyl group may properly C alkoxycarbonyl group) by substitution have been amino group, d alkyl represents an ₈ alkenyl group - optionally substituted Fuweniru group or be C i in group - alkoxy which may be substituted with a carbonyl group] C alkyl group or C _3. } 2. A compound represented by the formula (II) [I]

 (In the formula, X, Y and Z represent the same meaning as described above.)  A compound represented by the formula [I], wherein a compound represented by the formula: [I  X

 R (Wherein, X, Y, Ζ and R represent the same meaning as described above.) A method for producing an imidazole compound represented by 3. A herbicide characterized by containing one or more of the imidazole compounds represented by the formula [I] as an active ingredient.

 R  (In the formula, X, Υ, Ζ and R represent the same meaning as described above.)