JPH11158156A - New 1-(4-alkyloxyphenyl)imidazol compound - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject new compound useful as a synergist which has excellent synergistic activities with an insecticidal component, and useful as an active ingredient of a pest-controlling agent which has excellent pest- controlling activities. SOLUTION: This compound is a 1-(4-alkyloxyphenyl)imidazole compound of formula I R is an alkyl [having phenyl, naphthyl, cinnamyl or the like, (having a halogen atom as a substituent)]), for example, a compound of formula II. The compound of formula I is obtained, for example, by reacting 1-(4- hydroxyphenyl) imidazole with a compound of the formula X-R (X is a halogen). The compound of formula I is useful as an active ingredient of a pest-controlling agent and also useful as a synergist of a pest-controlling component. Allethrin, phthalthrin, resmethrin or the like is cited as the pest-controlling component with which the compound of formula I can manifest the synergistic activities.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a novel 1- (4-
The present invention relates to an (alkyloxyphenyl) imidazole compound, a method for producing the same, and a pesticide containing the compound.

[0002]

2. Description of the Related Art To date, various substances have been studied and developed as components for controlling pests. As one of them, a compound having an inhibitory action on insect hormones has been found as a component for controlling insect pests.

[0003] The development and reproduction of arthropods, including various insects, are governed by hormones. For example, molting and metamorphosis of larvae during development are mainly determined by juvenile hormones (Ju
Two hormones, venile hormone (hereinafter also referred to as JH) and molting hormone (Moulting hormone, also referred to as MH) are involved. If the relative balance of these insect hormones in the living body can be disturbed, normal growth of insects and the like is inhibited. Therefore, by utilizing this effect, it is possible to selectively cause only the desired pests to die without affecting humans and other animals,
Various studies have been made on these hormones and substances having the same action as these as new low-toxic pesticides, and they are attracting attention. The above JH is used for insect growth, reproduction,
It is a hormone related to dormancy and the like. For example, it is known that when an alata body secreting the JH is excised, normal larval molting cannot be repeated and the larva becomes an pupa or an adult (premature metamorphosis), and this JH activity is inhibited. Substance having an action (anti-JH
If an active substance is found, it also inhibits normal growth of pests, prematurely metamorphoses larvae, inhibits reproductive ability of adults and kills eggs, and has a small larvae due to premature metamorphosis. Since larvalization and shortening of the larval period occur, crop damage by the larvae can be reduced and the number of individuals can be reduced.

[0004] As such anti-JH active substances, 1,5
-Disubstituted imidazoles, 1-citronellyl-5-substituted imidazoles and the like are known.

[0005]

DISCLOSURE OF THE INVENTION The present inventors have conducted further intensive studies for the purpose of providing a compound having a new pest control effect. An object of the present invention is to provide a novel 1- (4)
-Alkyloxyphenyl) imidazole compounds. A further object of the present invention is to provide a novel 1-
An object of the present invention is to provide a method for producing a (4-alkyloxyphenyl) imidazole compound. Another object of the present invention is to
An object of the present invention is to provide a pest control agent having a novel synergist having an excellent synergistic effect on insecticidal components. Another object of the present invention is to provide a pesticidal agent having a novel pesticidal component and capable of exhibiting an excellent pesticidal effect.

[0006]

Means for Solving the Problems The present inventors have conducted intensive studies with the aim of providing a compound having a new pest control effect, and as a result, have been able to synthesize a novel 1- (4-alkyloxyphenyl) imidazole compound. Succeeded and achieved the above objectives. The configuration of the present invention is shown below. (1) A 1- (4-alkyloxyphenyl) imidazole compound represented by the following general formula (I).

[0007]

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In the formula (I), R represents an alkyl group which may have a substituent, provided that the substituent is a phenyl group which may have a halogen atom as a substituent.
Represents a naphthyl group, a cinnamyl group, a pyridyl group or a phenyloxy group. (2) 1- according to the above (1), wherein the alkyl group which may have a substituent for R has 4 to 11 carbon atoms in total.
(4-alkyloxyphenyl) imidazole compounds. (3) 1- (4-hydroxyphenyl) imidazole and XR (where R represents an alkyl group which may have a substituent, provided that the substituent is a halogen atom as a substituent It represents a phenyl group, a naphthyl group, a cinnamyl group, a pyridyl group or a phenyloxy group which may be present.
X represents a halogen atom. A) a compound represented by the following general formula (I):
A method for producing a-(4-alkyloxyphenyl) imidazole compound.

[0009]

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In the formula (I), R is as defined above. (4) A pest control agent comprising a 1- (4-alkyloxyphenyl) imidazole compound represented by the following general formula (I).

[0011]

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In the formula (I), R represents an alkyl group which may have a substituent, provided that the substituent is a phenyl group which may have a halogen atom as a substituent.
Represents a naphthyl group, a cinnamyl group, a pyridyl group or a phenyloxy group. (5) The pest control agent according to (4), wherein the 1- (4-alkyloxyphenyl) imidazole compound represented by the general formula (I) is contained as a pest control component. (6) The pest control agent according to (4), wherein the 1- (4-alkyloxyphenyl) imidazole compound represented by the general formula (I) is contained as a synergist of a pest control component. . (7) A synergist comprising a 1- (4-alkyloxyphenyl) imidazole compound represented by the following general formula (I).

[0013]

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In the formula (I), R represents an alkyl group which may have a substituent, provided that the substituent is a phenyl group which may have a halogen atom as a substituent,
Represents a naphthyl group, a cinnamyl group, a pyridyl group or a phenyloxy group.

[0015]

DESCRIPTION OF THE PREFERRED EMBODIMENTS Embodiments of the present invention will be described below in detail. R in the general formula (I) represents an alkyl group which may have a substituent. Examples of the alkyl group include those having 1 to 10 carbon atoms such as a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, and a decyl group. . Further, the alkyl group may have a substituent. Examples of the substituent include a phenyl group, a naphthyl group, a cinnamyl group, a pyridyl group and a phenyloxy group.
It may have two or more. Here, examples of the halogen atom include a chlorine atom, a bromine atom, a fluorine atom, and an iodine atom.

One or more of these substituents may be substituted at any position of the above-mentioned alkyl group, but at least one is bonded to the terminal of the alkyl group opposite to -O-. Is preferred. In the present invention, R
The total number of carbon atoms of the optionally substituted alkyl group is 4
~ 11 are preferred. Hereinafter, specific examples (I-1) to (I-17) of the 1- (4-alkyloxyphenyl) imidazole compound represented by the general formula (I) are shown, but the content of the present invention is not limited thereto. Not something.

[0017]

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[0018]

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In the present invention, the method for producing the 1- (4-alkyloxyphenyl) imidazole compound represented by the general formula (I) includes 1- (4-hydroxyphenyl) imidazole and XR Wherein R is as defined above, and X represents a halogen atom.) This reaction is carried out in a suitable solvent such as, for example, dimethylformamide.
For example, it can be carried out using sodium hydride (NaH) or the like.

The ratio of the starting compounds used, the reaction conditions and the like can be determined appropriately. As a guide, each raw material compound and NaH can usually be used in equimolar amounts. In addition, the reaction temperature usually proceeds at or around room temperature. After completion of the reaction, the target substance can be isolated and purified by a usual separation operation, for example, ether extraction, distillation, and column chromatography. 1- which is the raw material
(4-Hydroxyphenyl) imidazole manufactured by Aldrich can be used, and the compound represented by XR (alkyl halide) is 3- (4-chlorophenyloxy) propyl bromide and 2- (4-chlorophenyloxy) Ethyl bromide can be combined with 4-chlorophenol and 1,3-dibromopropane or 1,2-
It can be synthesized by reaction with dibromoethane. Other X
As -R, a commercially available product can be used.

Hereinafter, the pest control agent of the present invention will be described. The 1- (4-alkyloxyphenyl) imidazole compound represented by the above general formula (I) is useful as a synergist for a pest control component or as a pest control component.

In the present invention, the compound represented by the above general formula (I) is effective as a synergist for a component for controlling pests.
Examples of the insect pest-controlling component in which the compound represented by the general formula (I) can exert a synergistic effect include the following. ○ 3-allyl-2-methylcyclopent-2-ene-
4-one-1-yl dl-cis / trans-chrysanthemate (generic name: arrestrin) ○ 3-allyl-2-methylcyclopent-2-ene-
4-one-1-yl d-cis / trans-chrysanthemate (trade name: Pinamine Forte: manufactured by Sumitomo Chemical Co., Ltd.) ○ d-3-allyl-2-methylcyclopenta-2-en-4-one -1-yl d-trans-chrysanthemate (trade name: Exulin: manufactured by Sumitomo Chemical Co., Ltd.) ○ 3-allyl-2-methylcyclopenta-2-ene-
4-one-1-yl d-trans-chrysanthemate (general name: bioaresulin) N- (3,4,5,6-tetrahydrophthalimide)
-Methyl dl-cis / trans-chrysanthemate (common name phthalthrine) ○ 5-Benzyl-3-furylmethyl d-cis / trans-chrysanthemate (common name resmethrin)

２− 2-methyl-5- (2-propargyl)
-3-furylmethyl chrysanthemate (common name: flamethrin) ○ 3-phenoxybenzyl 2,2-dimethyl-3-
(2 ′, 2′-dichloro) vinylcyclopropane carboxylate (generic name permethrin) ○ 3-phenoxybenzyl d-cis / trans-chrysanthemate (generic name phenothrin) ○ α-cyano-3′-phenoxybenzyl α- Isopropyl-4-chlorophenyl acetate (generic name fenvalerate) O, O-dimethyl O- (2,2-dichloro) vinyl phosphate (DDVP) O, O-dimethyl O- (3-methyl-4-nitrophenyl) Thionophosphate (Sumithion) O, O-dimethyl O-2-isopropyl-4-methyl-pyrimidyl- (6) -thiophosphate (diazinone) O, O-dimethyl S- (1,2-dicarbethoxy) Ethyl) -dithiophosphate (marathon) O-isopropoxyf Enyl methyl carbamate (Vigon) ○ O- (4-bromo-2,5-dichlorophenyl)
O, O-dimethyl phosphorothioate (bromophos)

The content of the compound represented by the general formula (I) in the pesticidal composition containing the compound represented by the general formula (I) of the present invention as a synergist is based on the total weight of the pesticide. It is preferably from 0.1 to 95% by weight, more preferably from 0.5 to 90% by weight. Further, the content of the pest controlling component in the pest controlling agent is preferably 0.1 to 95% by weight, more preferably 0.5 to 90% by weight. Among the above pest control components, those in which the compound represented by the general formula (I) of the present invention can more effectively exert a synergistic effect are preferably pyrethroid compounds, organophosphorus compounds, carbamate compounds, And juvenile hormone-like compounds (methoprene and the like).

In the present invention, the compound represented by the above general formula (I) is further effective as a component for controlling pests. The content of the compound represented by the general formula (I) in the pesticidal composition of the present invention, which is contained as a component for controlling a pest, is 0. 0 to the total weight of the pesticide.
It is preferably from 1 to 95% by weight, more preferably from 0.5 to 9% by weight.
0% by weight. This pest control agent can be further diluted in actual application, and the concentration of the compound represented by the general formula (I) of the present invention can be varied over a wide range. It can be 0.0001 to 10%, preferably 0.01 to 1%. The pest control agent of the present invention can be used in combination with an active compound such as another pest control component or a synergist.

The pesticidal composition containing the compound represented by the general formula (I) in the present invention can be used as it is or in an appropriate preparation form such as a solution, emulsion, suspension, powder, paste, capsule, granule and the like. After shaping, it is applied to the pests required to be controlled, their habitats, the crops required to be controlled and their cultivated areas by a usual method such as spraying, spraying, and stripping.

The above-mentioned preparations can be prepared in a known manner, for example, by adding a compound represented by the general formula (I) of the present invention to a bulking agent, ie, a liquid or solid carrier and, if necessary, a liquefied gas, LPG, propane, butane, pentane, dimethyl ether. And a propellant such as chlorofluorocarbon and a surfactant (emulsifier, foaming agent, dispersant, etc.). Examples of the liquid carrier include aromatic hydrocarbons such as xylene, toluene, benzene, and alkylnaphthalene; chlorinated aromatic or aliphatic hydrocarbons such as chlorobenzene, chloroethylene and methylene chloride; aliphatic hydrocarbons such as cyclohexane and paraffin; Fraction;
Alcohols such as butanol and glycol and ethers and esters thereof; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone;
Examples thereof include polar solvents such as dimethylformamide, dimethylsulfoxide, acetonitrile, and water.

Examples of the solid carrier include natural mineral powders such as kaolin, clay, talc, calcium carbonate, chalk, quartz, titanium, atabalgit, montmorillonite and diatomaceous earth, and synthetic mineral powders such as silicic acid, alumina and silicate. . Examples of the emulsifier, foaming agent and dispersant include polyoxyethylene-fatty acid ester, polyoxyethylene-fatty alcohol ether, alkylaryl polyglycol ether, alkyl sulfonate, alkyl sulfate, aryl sulfonate, albumin hydrolyzate, lignin, sulfite Examples include waste liquid and methylcellulose.

The pests that can be controlled by the present invention are not limited as long as they exhibit a controlling effect, but include various insects, mites, nematodes, and arthropods that harm humans and animals. be able to. The following are examples of the pests. Pests of the order Lepidoptera include Japanese moth, coffee beetle molybdenum, apple stag, apple pine,
Bacga, Futrimaea Operculera, Amimenamishiya, Tenghamaki, Kakoea Mulinana, Tortrix bilina, Grape Hosohamaki, Eseteria Buoliana, Polycrosis Botlana, Side Apomonera, Las Pelesia Moresta, Las Peilecia Funebrane, Awanome Geyera, Awanome Gesera Hachinotsu Periga, Obikareha, Dendrolimus Pini,
Samatoponia piteocampa, atmonhirozukoga,
Namiz Zihu Yunami Saku, Hypernia DeHoliaria,
Bpulse Pinealus, American White Star, Kaburayaga, Hitotenkenmon, Japanese Milkworm, Purple Honeybee, Common Lotus, Spodoptera litura, Panoris Flamea, Benimon Aolinga, Kinuwaba, Alabama Algiracea, Kashiwamaiigai, Gychodidae, Mongolia

In the eyes of the order Coleoptera, there are Semaphoridae, Melanotus communis, Lumonium californicus, Kometsuki, Kabairokometsuki, Nagatamushi, Marigetes anames, Atmaria linealis, Nijuyashitento, Ushukokogane, Ogama, Podfish Solstitialis, Coleoptera beetle, Kubohoso beetle, Leptionar sassensen lineata, Radish beetle, Flea beetle, Flying beetle, Eggplant flea beetle, Diablotica 12-panclata, Himezingasa, Soybean weevil, Soybean weevil, Tibicho aphistis Cutiska specturae, ansonomus pomorum, ooff Bikiyoto, Blue mushroom armyworm, Seo iso Craiglynne dregs Napi, Shitofirasu
Granaria, Ips Tapographas, Blastfagus Pinipelda, etc. belong.

In the eyes of Diptere, licorice pectralis, Maietiora destructor, Larix metaphoridae, Mabae, Tiprapardosa, Tipraoleracea, Urimi fly, Citrus fly, Seratitis
Capitata, Lagoletis Therapy, Lagoletis Pomanella, Anatolefa Ludense, Otsinella Frit, Forbia Koalactata, Forbia Antica, Hakobemoguri Flies, Akazamoguri Flies,
Anofeles Maclipenis, Curex Pipiens, Aedes Aegipti, Aedes Bexans, Tabanas Bobinus, Tiprapaldoza, Housefly, Fania Curriculis, Mutsina Stavulans, Grossina Morcitans, Estrus Ocis, Chrysomiyama maceraria, Chrysomiya Hominiborax
Lucyia Cyprina, Lucyia Sericata, Hippoderma Lineata, etc. belong.

The eyes of Hymenoptera belong to the order of Capra wasp, Haplocampa minuta, Himeari, Solenopsis dieminata, Ata tex dense and the like. In the eyes of the Hemiptera, southern stink bugs, brown stink bugs, brown stink bugs, vilysium leucopteras, red beetle stink bugs, Dysdelcas intermedeas, Piezma cadratata, Mekuraga turtle, Oshiuka, Tobirouka, Matsuhimemebira, Rabbit biloba Affith fabae, Apple aphid, Elderberry aphid, Affijura nastyullaus, Serusia gossypia, Sapaphis mari, Sapaphis mara, Neaphisi, Brachikandas caldoi, Radish aphid,
Hot-aphid aphid, Wheat viper aphid, Mizodes persisae, Mizuserathesy, Sisaura Coltham
Pseudosorami, Aphid aphid, Macrosiphon rosae, Broad bean aphid, Shizoneura
Lanuginosa, Penfigs bursalius, Dreyfusia nordanea, Dreyfusia pisea, Mycasa aphid, Grapea aphid, etc. belong.

In the eyes of the order Isoptera, reticulitermes lucifugas, caroterumes flavicoris,
Leukotelmis flavipes, Termes natalensis, etc. belong. In the eyes of Orthoptera (0rthoptera), Forficula Ouricularia, Acita Domestica, Grylotapura Grylotapura, Tatsuxines asinamoras, Locastamigratria, Stauronotas Marotskanas, Cystcella Peregrina, Nomadaklis
Septen Fassiata, Melano Plus Spruce,
Melanoplus Femurulblum, Brata Orientalis, German cockroach, Periplaneta Americana, Bravelaziganthea, etc. belong.

In the order of Acarina, house dust mites, mites, mites, fly mites, fly mites, red mites, mite mites, mites mites, sugar mites,
In addition to Dermatophagoides farinae, Dermatophagoides farinae, Dermatophagoides farinae, Dermatophagoides, Dermatophagoides, Dust mites, Dermatophagoides, Dermatophagoides, Dermatophagoids, Dermatophagoides, Dermatophagoides and the like.

As the nematodes, nematodes such as rootworm nematodes, ie, meloidinine cognita, meloid papura, meloidine japonica, cyst-forming nematodes, ie, heterodera lostensis, heterodera satchii, heterodera avena, heterodera gricines, heterodera trifolia Lee, stem and chlorophyll, i.e., ditilencus depsis, ditilencus destructor, platinum neglectus, platinum nspenetrans, platinum nectar
Goody, Platinenkas curvitatas, Cylenechorinkus Dovius, Cillenchorinkus Claytoni, Lotirenkas Robustus, Herilokotyrencus
Multisintas, Radophorus similis, Peronolimes Longikaudatas, Longidras elongatas, Trichodrus primitives, etc. belong.

[0036]

[Synthesis of Compound Represented by General Formula (I)]

Synthesis Example 1 (Compound I-1) 0.33 g of sodium hydride (60% in liquid paraffin) was suspended in 10 ml of dimethylformamide, and 0 to 5 ° C.
And cooled. 1 g of 1- (4-hydroxyphenyl) imidazole was added thereto, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was ice-cooled, and 0.79 g of benzyl chloride was added.
Stir at room temperature for 4 hours. 50 ml of water was added to the reaction mixture,
The resulting precipitate was separated by filtration and recrystallized from isopropyl ether to obtain 0.4 g (yield 26%) of the desired product (I-1). 110-111 ° C. NMR (CDCl ₃ ) δ: 5.11 (2H, s), 7.06 (2H, d, J = 8.5 H
z), 7.19 (2H, d, J = 8.5 Hz), 7.22-7.48 (7H, m), 7.76 (1
H, s). Elemental analysis (C ₁₆ H ₁₄ N ₂ O) Found: C, 76.48; H, 5.64; N, 10.95% Calculated: C, 76.80; H, 5.60; N, 11.20%.

Synthesis Example 2 (Compound I-2) The procedure of Synthesis Example 1 was repeated except that phenethyl bromide was used instead of benzyl chloride.
Phenethyloxyphenyl) imidazole (I-2) was synthesized. NMR δ (CDCl ₃ ): 3.03-3.07 (2H, t, J = 6.8Hz), 4.12-
4.15 (2H, t, J = 7.1Hz), 6.88-6.92 (2H, m), 7.10-7.28 (9
H, m), 7.67 (1H, s)

Synthesis Example 3 (Compound I-3) 1- [4- (4-chlorobenzyl) was prepared in the same manner as in Synthesis Example 1 except that 4-chlorobenzyl chloride was used instead of the above benzyl chloride. [Oxy) phenyl] imidazole (I-3) was synthesized. NMR δ (CDCl ₃ ): 5.07 (2H, s), 7.02-7.31 (10H, m),
7.37 (1H, s)

Synthesis Example 4 (Compound I-4) 1- [4- (3-chlorobenzyl) was prepared in the same manner as in Synthesis Example 1 except that 3-chlorobenzyl chloride was used instead of benzyl chloride. [Oxy) phenyl] imidazole (I-4) was synthesized. NMR δ (CDCl ₃ ): 5.07 (2H, s), 7.01-7.05 (2H, m), 7.
18-7.20 (2H, d, J = 6.8Hz), 7.27-7.35 (5H, m), 7.44 (1
H, s), 7.75 (1H, s)

Synthesis Example 5 (Compound I-5) 1- [4- (2-chlorobenzyl) was prepared in the same manner as in Synthesis Example 1 except that 2-chlorobenzyl chloride was used instead of benzyl chloride. [Oxy) phenyl] imidazole (I-5) was synthesized. NMR δ (CDCl ₃ ): 5.14-5.17 (2H, d, J = 12.7Hz), 7.01-
7.38 (9H, m), 7.53 (1H, s), 7.73-7.74 (1H, d, J = 7.3Hz)

Synthesis Example 6 (Compound I-6) The procedure of Synthesis Example 1 was repeated except that 3-chloromethylpyridine was used instead of benzyl chloride.
1- [4- (3-Picolyloxy) phenyl] imidazole (I-6) was synthesized. NMR δ (CDCl ₃ ): 5.12 (2H, s), 7.05-7.07 (2H, m), 7.
19-7.21 (2H, m), 7.28-7.36 (3H, m), 7.77-7.80 (2H, m),
8.60-8.62 (1H, m), 8.70 (1H, s)

Synthesis Example 7 (Compound I-7) 1- [4- (2-naphthyl) was prepared in the same manner as in Synthesis Example 1 except that 2- (bromomethyl) naphthalene was used instead of benzyl chloride. [Methyloxy) phenyl] imidazole (I-7) was synthesized. NMR δ (CDCl ₃ ): 5.26 (2H, s), 7.07-7.43 (6H, m), 7.
47-7.55 (3H, m), 7.76-7.89 (5H, m)

Synthesis Example 8 (Compound I-8) The same procedure as in Synthesis Example 1 was repeated except that cinnamyl bromide was used instead of benzyl chloride.
(4-Cinnamyloxyphenyl) imidazole (I-
8) was synthesized. NMR δ (CDCl ₃ ): 4.74 (2H, dd, J = 1.5Hz, 5.9Hz), 6.
41 (1H, dt, J = 16Hz, 5.9Hz), 6.75 (1H, d, J = 16Hz), 7.
02-7.06 (2H, m), 7.18-7.20 (2H, m), 7.25-7.43 (7H, m),
7.76 (1H, s)

Synthesis Example 9 (Compound I-9) 1-Bromooctane was used in the same manner as in Synthesis Example 1 except that 1-bromooctane was used instead of benzyl chloride.
(4-octyloxyphenyl) imidazole (I-
9) was synthesized. NMR δ (CDCl ₃ ): 0.89 (3H, t, J = 6.3 Hz), 1.30-1.47 (1
0H, m), 1.76-1.83 (2H, m), 3.97 (2H, t, J = 6.6Hz), 6.
95 (2H, d, J = 8.8Hz), 7.16 (1H, s), 7.18 (1H, s), 7.25
(2H, d, J = 8.8Hz), 7.74 (1H, s)

Synthesis Example 10 (Compound I-10) 1- [4- (2-fluorobenzyl) was prepared in the same manner as in Synthesis Example 1 except that 2-fluorobenzyl chloride was used instead of benzyl chloride. [Oxy) phenyl] imidazole (I-10) was synthesized. NMR δ (CDCl ₃ ): 5.17 (2H, s), 7.05-7.36 (9H, m), 7.
49-7.52 (1H, m), 7.76 (1H, s)

Synthesis Example 11 (Compound I-11) 1- [4- (3-Fluorobenzyl) was prepared in the same manner as in Synthesis Example 1 except that 3-fluorobenzyl chloride was used instead of the above-mentioned benzyl chloride. [Oxy) phenyl] imidazole (I-11) was synthesized. NMR δ (CDCl ₃ ): 5.10 (2H, s), 7.01-7.39 (10H, m),
7.76 (1H, s)

Synthesis Example 12 (Compound I-12) 1- [4- (4-fluorobenzyl) was prepared in the same manner as in Synthesis Example 1 except that 4-fluorobenzyl chloride was used instead of benzyl chloride. [Oxy) phenyl] imidazole (I-12) was synthesized. NMR δ (CDCl ₃ ): 5.06 (2H, s), 7.02-7.43 (10H, m),
7.76 (1H, s)

Synthesis Example 13 (Compound I-13) 1- (4) was prepared in the same manner as in Synthesis Example 1 except that 1-bromobutane was used instead of benzyl chloride.
-Butyloxyphenyl) imidazole (I-13) was synthesized. NMR δ (CDCl ₃ ): 0.99 (3H, t, J = 7.3 Hz), 1.46-1.56 (2
H, m), 1.76-1.82 (2H, m), 3.99 (2H, d, J = 6.4Hz), 6.97
(2H, d, J = 8.8Hz), 7.17 (1H, s), 7.19 (1H, s), 7.27 (2H,
d, J = 8.8Hz), 7.75 (1H, s)

Synthesis Example 14 (Compound I-14) 1- (4) was prepared in the same manner as in Synthesis Example 1 except that 1-bromodecane was used instead of benzyl chloride.
-Decyloxyphenyl) imidazole (I-14) was synthesized. NMR δ (CDCl ₃ ): 0.89 (3H, t, J = 6.8 Hz), 1.28-1.38 (1
2H, m), 1.43-1.50 (2H, m), 1.77-1.84 (2H, m), 3.98 (2
H, t, J = 6.8Hz), 6.96 (2H, d, J = 8.5Hz), 7.18 (1H, s),
7.20 (1H, s), 7.28 (2H, d, J = 8.5Hz), 7.75 (1H, s)

Synthesis Example 15 (Compound I-15) The procedure of Synthesis Example 1 was repeated, except that 3- (4-chlorophenyloxy) propyl bromide was used instead of benzyl chloride. [3- (4
-Chlorophenyloxy) purpyroxy] phenyl]
Imidazole (I-15) was synthesized. NMR δ (CDCl ₃ ): 2.24-2.30 (2H, m), 4.13 (2H, t, J =
6.1Hz), 4.18 (2H, t, J = 6.1Hz), 6.81-6.85 (2H, m), 6.9
6-7.00 (2H, m), 7.17-7.20 (6H, m), 7.74 (1H, s)

Synthesis Example 16 (Compound I-16) The procedure of Synthesis Example 1 was repeated except that 2- (4-chlorophenyloxy) ethyl bromide was used instead of benzyl chloride. [2- (4-Chlorophenyloxy) ethyloxy] phenyl] imidazole (I-16) was synthesized. NMR δ (CDCl ₃ ): 4.31-4.34 (4H, m), 6.87-7.31 (10H,
m), 7.76 (1H, s)

Synthesis Example 17 (Compound I-17) Except that 1-bromohexane was used instead of benzyl chloride, 1-bromohexane was prepared in the same manner as in Synthesis Example 1 above.
(4-hexyloxyphenyl) imidazole (I-1)
7) was synthesized. NMR δ (CDCl ₃ ): 0.92 (3H, t, J = 7.1 Hz), 1.29-1.51 (6
H, m), 1.75-1.86 (2H, m), 3.99 (2H, t, J = 6.6Hz), 6.97
(2H, d, J = 9.0Hz), 7.18 (1H, s), 7.20 (1H, s), 7.28 (2
H, d, J = 9.0Hz), 7.76 (1H, s)

Example 1 (Test compound) As a synergist, the compound represented by the general formula (I) of the present invention (listed in Tables 1 to 3 below) was used as a pyrethroid-based compound using a cat flea adult. The synergistic effect on minforte (dl · d-T80-aresulin) was examined. In addition, piperonyl butoxide (also referred to as PBO) was used as a comparative compound. These compounds as synergists were mixed with pinamine forte at a weight mixing ratio of 1: 1 to obtain test compounds. As a control, only pinamine forte was used.

(Test Insects) As cat flea adults, 25 ±
Reared at 2 ° C, about 75% RH and escaped from the cocoon for 24 hours.
Unblooded individuals (mixed male and female) within hours were tested.

(Test method) One test insect was pinched with tweezers, immersed instantaneously (about 0.5 seconds) in an acetone solution of each of the test compounds diluted to a predetermined concentration, and immediately placed on a tissue paper. The test insects were placed on the sample to remove the excess drug solution. Then, a filter paper with a diameter of 7 cm (No. 2) is placed on the bottom.
Plastic petri dish (diameter 9cm, height 1.8)
cm), each of which contains 10 test insects, and 20
The head was tested. Thereafter, the number of supine insects and the number of dead insects were examined with time, and the values were converted to probits.
The LC ₅₀ value (50% lethal concentration) after hours and 48 hours was determined. The test was performed in a constant temperature room at 25 ± 2 ° C. The results are shown in Table 1 below. In addition, for each of the test compounds described above, 24 hours after the start of the test at the concentrations described in Tables 2 and 3,
The turnover rate and mortality after 48 hours were examined. The results are shown in Tables 2 and 3 below.

[0056]

[Table 1]

[0057]

[Table 2]

[0058]

[Table 3]

As can be seen from Tables 1 to 3, the compounds of the present invention exhibited synergistic effects on pinamine forte which were equal to or higher than those of the comparative compound using PBO. Compound I-
1, I-7, I-9, I-10, I-11, I-14,
I-17 exhibited a particularly high synergistic effect, and the effect was higher than that of the control PBO.

Example 2 (Test compounds) The compounds represented by the general formula (I) of the present invention (the compounds listed in Table 4 below) were examined for their insecticidal effect against the last instar larvae of Culex pipiens, and To study the synergistic effect on methoprene. When examining the insecticidal effect, each compound is used as a test compound. When examining the synergistic effect on methoprene, a mixture of each compound and methoprene (weight ratio of 5: 1) is used.
Was used as a test compound. In addition, PBO,
SA-16 and KK-42 having the following structure were used. When synergistic effect was examined, only methoprene was used as a control.

[0061]

Embedded image

(Test Method) 100 ml of deionized water was placed in a plastic container (bottom diameter 9 cm, height 4.5 cm).
100 μl of an acetone solution of the test compound diluted to a predetermined concentration was added thereto to prepare a test solution. After releasing 20 test insects into this container, a small amount of feed (a mixture of ground yeast solid feed and dry yeast mixed at a ratio of 1: 1) was given.
The vessel was covered and the water temperature was kept at about 25 ° C. Then 2
From 4 hours to 48 hours, the pupated individual was collected, placed in another plastic container (bottom diameter 9 cm, height 4.5 cm) containing 100 ml of deionized water, covered, and the water temperature was reduced to about 25.
C. Individuals that died from 24 hours to 48 hours were also counted as test insects. Thereafter, after examining the rate of emergence for each treatment group performs Abbot correction, it calculates the correction emergence inhibition rate, mortality was probit transformation, IC ₅₀ values were determined. Here, the IC ₅₀ value is a 50% eclosion inhibitory concentration. Each test was performed four times. Table 4 shows the results of the insecticidal effect (corrected eclosion inhibition rate) of each compound, and Table 5 shows the results of the synergistic effect.

[0063]

[Table 4]

[0064]

[Table 5]

Referring to Table 4 showing the inhibitory effect on emergence of the above compounds against the last instar larvae of Culex pipiens, the compound exhibiting the highest inhibitory effect on emergence was I-9, showing a corrected emergence inhibition ratio of 69.8%. I-1 also showed a corrected eclosion inhibition rate of 15.6%. On the other hand, SA-16 and KK-42 had a low eclosion inhibitory effect, and piperonyl butoxide had no effect. Looking at Table 5, which shows the synergistic effect of each compound on methoprene, the compounds of the present invention showed a high synergistic effect.
On the other hand, compared to the compound of the present invention, SA-16, KK-4
2. The synergistic effect of piperonyl butoxide was low.

[0066]

According to the present invention, a novel 1- (4-alkyloxyphenyl) imidazole compound and a method for producing the same can be provided. Further, it is possible to provide a pest control agent having a novel synergist having an excellent synergistic effect on an insecticide component, or a pest control agent having a novel insecticide component and exhibiting an excellent pest control effect.

Claims (7)

[Claims] 1- (4-) represented by the following general formula (I)
Alkyloxyphenyl) imidazole compounds. Embedded image In the formula (I), R represents an alkyl group which may have a substituent, provided that the substituent includes a phenyl group, a naphthyl group, which may have a halogen atom as a substituent.
Represents a cinnamyl group, a pyridyl group or a phenyloxy group. 2. The 1- (4-alkyloxyphenyl) imidazole compound according to claim 1, wherein the alkyl group which may have a substituent for R has 4 to 11 carbon atoms in total. 3. 1- (4-hydroxyphenyl) imidazole, and XR (where R represents an alkyl group which may have a substituent, provided that the substituent is a halogen atom) It represents a phenyl group, a naphthyl group, a cinnamyl group, a pyridyl group or a phenyloxy group which may have as a group.
X represents a halogen atom. A) a compound represented by the following general formula (I):
A method for producing a-(4-alkyloxyphenyl) imidazole compound. Embedded image In the formula (I), R has the same meaning as described above. 4. A compound represented by the following general formula (I):
A pest control agent comprising an (alkyloxyphenyl) imidazole compound. Embedded image In the formula (I), R represents an alkyl group which may have a substituent, provided that the substituent includes a phenyl group, a naphthyl group, which may have a halogen atom as a substituent.
Represents a cinnamyl group, a pyridyl group or a phenyloxy group. 5. 1- (4-) represented by the general formula (I)
The pest control agent according to claim 4, wherein the (alkyloxyphenyl) imidazole compound is contained as a pest control component. 6. 1- (4-) represented by the general formula (I)
The insect-controlling agent according to claim 4, wherein the compound (alkyloxyphenyl) imidazole compound is contained as a synergist of the insect-controlling component. 7. 1- (4-) represented by the following general formula (I)
A synergist comprising an (alkyloxyphenyl) imidazole compound. Embedded image In the formula (I), R represents an alkyl group which may have a substituent, provided that the substituent includes a phenyl group, a naphthyl group, which may have a halogen atom as a substituent.
Represents a cinnamyl group, a pyridyl group or a phenyloxy group.