JPH064600B2 - 1-citronellyl-5-substituted imidazoles - Google Patents

Description

TECHNICAL FIELD The present invention relates to 1-citronellyl-5-substituted imidazoles, a method for producing the same and an anti-juvenile hormone activator.

BACKGROUND ART The development and reproduction of arthropods including various insects are dominated by hormones. For example, the molting and metamorphosis of larvae found during development are mainly juvenile hormones.
e hormone, JH) and molting hormone (Mou
two hormones, namely, the swelling hormone (MH). If the relative balance of these insect hormones in the living body can be disturbed, the normal growth of insects is hindered. Therefore, if this effect is utilized, it is possible to selectively kill only the target pest without affecting humans or other animals. A variety of substances having the following are being researched and developed as new low-toxic pest control agents and are attracting attention. Further, the above JH is a hormone related to insect growth, reproduction, dormancy, etc. For example, if the Arata body secreting the JH is excised, normal larval molting cannot be repeated and a pupa or an adult (precocious metamorphosis) occurs. Is known, this J
Substances that have the effect of inhibiting H activity (anti-JH active substances)
If this is found, it also inhibits the normal development of pests, transforms the larvae into precocious metamorphosis, and also has the effect of inhibiting fertility of adults and ovicidal action. Since the period is shortened, crop damage caused by larvae can be reduced and the number of individuals can be reduced.

OBJECT OF THE INVENTION From the above viewpoints, the present inventors have earnestly studied for the purpose of providing an anti-JH active substance that can be used as a new hormone-based insect pest control agent, and as a result, a series of compounds represented by the following general formula (I) was obtained. We have succeeded in synthesizing 1-citronellyl-5-substituted imidazoles and found that these compounds meet the above-mentioned object, and thus completed the present invention.

Structure of the Invention That is, the present invention is a general formula [In the formula, R represents a phenyl group having a halogen atom, a lower alkoxy group or a methylenedioxy group as a substituent. ] A 1-citronellyl-5-substituted imidazole represented by the following, a method for producing the same, and an anti-juvenile hormone activator containing the compound.

In the above general formula (I), the halogen atom of the substituent in the substituted phenyl group defined by R is chlorine, fluorine,
Examples of iodine and bromine, and examples of the lower alkoxy group include methoxy, ethoxy, propoxy, isopropoxy and butoxy groups. An equal substituent is 2 on the phenyl ring.
It may be present at any of the-, 3- and 4-positions, and a plurality thereof may be present.

The compound of the present invention represented by the above general formula (I) can be produced, for example, by the method shown in the following reaction scheme.

<Reaction formula-1> [Wherein R and R'are the same as above. That is, according to Reaction Formula-1, the known imidazole compound (I
The compound (I) of the present invention can be produced by reacting I) with the citronellol derivative (III). The above reaction is
It is carried out in a suitable solvent such as dimethylformamide, for example, using sodium hydride (NaH) and the like. The use ratio of the raw material compound, the reaction conditions and the like are appropriately determined and are not particularly limited, but usually each raw material compound and NaH are preferably used in equimolar amounts, preferably a slight excess of the citronellol derivative (III) is used, and the reaction is Proceed at or near room temperature. After the completion of the reaction, the desired product can be isolated and purified by a conventional separation means such as ether extraction, distillation and column chromatography.

<Reaction formula-2> [Wherein R is the same as above. According to Reaction Formula-2, the compound (I) of the present invention can be produced by reacting the imine compound (III) with tosylmethyl isocyanide IV. The reaction is carried out in a solvent such as an alcohol such as methanol or an ether such as dimethoxyethane, in the presence of an inorganic base such as potassium carbonate or sodium carbonate or an organic base such as isopropylamine or t-butylamine, preferably at room temperature or It is carried out under temperature conditions in the vicinity. Although the use ratio of the raw material compound is not limited, usually to the imine compound (III), at least equimolar amount of tosylmethyl isocyanide (IV), preferably about 1 to 1.5 times the molar amount and at least the basic compound. It is preferable to use a molar amount, preferably about 2-3 times the molar amount. The imine compound (III) as a raw material can be obtained by reacting a corresponding aldehyde with citronellylamine.

The method shown in the above Reaction Scheme-2 is preferable, as compared with the method shown in the above Reaction Scheme-1, because there is no fear of isomer by-product and the target product can be obtained in a higher yield.

After the completion of the reaction, the desired product can be isolated by usual separation and purification means.

The thus-obtained compounds of the present invention represented by the general formula (I) all have antijuvenile hormone activity (anti-JH activity, precocious activity), and as an anti-JH activator, as described above, It is useful as a hormonal pest control agent.

When the compound of the present invention is used as the pest control agent, it may be used as it is or after being shaped into a suitable formulation such as a solution, emulsion, suspension, powder, paste, capsule, granule, etc. The method is applied to, for example, pests required to be controlled, their habitat, agricultural crops required to be controlled, and their cultivating places by spraying, spraying, removing, etc.

The above-mentioned preparations are prepared by a known method, for example, by adding the compound of the present invention to a bulking agent, that is, a liquid or solid carrier and optionally a liquefied gas
It is prepared by mixing with a propellant such as Freon and a surface active agent (emulsifier, foaming agent, dispersant, etc.). As the liquid carrier, 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;
Mineral oil fractions; alcohols such as butanol and glycol and their ethers and esters; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone; polar solvents such as dimethylformamide, dimethyl sulfoxide, acetonitrile and water. Examples of the solid carrier include natural mineral powders such as kaolin, clay, talc, chalk, quartz, attabulgite, montmorillonite and diatomaceous earth, and synthetic mineral powders such as silicic acid, alumina and silicate.

As the emulsifier, the foaming agent and the dispersant, polyoxyethylene-fatty acid ester, polyoxyethylene-fatty alcohol ether, alkylaryl polyglycol ether, alkyl sulfonate, alkyl sulfate,
Examples thereof include aryl sulfonate, albumin hydrolysis product, lignin, sulfite waste liquid, and methyl cellulose.

The compounds of the present invention can also be used in combination with active compounds such as other insecticides.

The active compounds include those shown below.

3-allyl-2-methylcyclopent-2-ene-4
-On-1-yl dl-cis / trans-chrysanthemate (generic name allethrin) 3-allyl-2-methylcyclopent-2-ene-4
-On-1-yl d-cis / trans-chrysanthemate (trade name Pinamine Forte: manufactured by Sumitomo Chemical Co., Ltd.) d-3-allyl-2-methylcyclopent-2-en-4-one-1 -Yl d-trans-chrysanthate (trade name: Exulin: manufactured by Sumitomo Chemical Co., Ltd.) 3-allyl-2-methylcyclopent-2-ene-4
-On-1-yl d-trans-chrysanthemate (generic name bioallethrin) N- (3,4,5,6-tetrahydrophthalimide)-
Methyl dl-cis / trans-chrysanthemate (generic name phthalthrin) 5-benzyl-3-furylmethyl d-cis / trans-chrysanthemate (generic name resmethrin) 2-methyl-5- (2-propargyl) -3 -Furylmethyl chrysanthemate (generic name flamethrin) 3-phenoxybenzyl 2,2-dimethyl-3-
(2 ', 2'-Dichloro) vinylcyclopropane carboxylate (generic name permethrin) 3-phenoxybenzyl d-cis / trans-chrysanthate (generic name phenothrin) a-cyano-3'-phenoxybenzyl a-Isopropyl-4-chlorophenylacetate (generic name phenvalerate) 0,0-dimethyl 0- (2,2-dichloro) vinyl phosphate (DDVP) 0,0-dimethyl 0- (3-methyl-4-nitro) Phenyl) thionophosphate (Sumithion) 0,0-dimethyl 0-2-isopropyl-4-methyl-pyrimidyl- (6) -thiophosphate (Diazinone) 0,0-dimethyl S- (1,2) -Dicarboethoxyethyl) -dithiophosphate (marathon) 0-isopropoxyphenyl methylcarbamme Preparative (bigon) 0- (4-bromo-2,5-dichlorophenyl) 0,
0-Dimethylphosphorothioate (Bromofus) Generally, the preparation contains 0.1 to 95% (wt%, the same applies hereinafter), preferably 0.5 to 90% of the compound of the present invention. This formulation can be further diluted for practical application, and the concentration of the compound of the present invention can be varied over a wide range, generally 0.0001 to 10%, preferably 0.01 to 1%. Can be

The pests that can be controlled by the compound of the present invention are not limited as long as their development and reproduction are controlled by hormones, and various insects, mites, nematodes, and arthropods that harm humans Including all of. Representative examples of the above-mentioned pests are given below.

For the pests of Lepidoptera, diamondback moth (Plutella macul)
ipennis), coffee mon shiromoriga (Leucoptera coffee
lla), Apple Suga (Hyponomeuta malinellus), Apple Himesink (Argyresthia conjugella), Pakuga (Sitotroga)
erealella), Futurimaea Opelculera (Phthorim
aea operculella), Amy operculella (Capue reticulan)
a), Sparganohis pilleriana, Cacoecia murinana, Tortrix viridana, Clysi
a ambiguella), Esetria buo-
liana), Polychrosis botran
a), Cydia pomonella, Laspeyresia molesta, L. funebrana, Awanomeiga
inia nubilalis), Loxosteguee stake taikaris
(Loxostege sticticalis), Ephestia kuehuiella, Nikamaiga (Chilo suppre)
ssalis), Hachinosu Tsurigiga (Galleria mellonella), Obikareha (Malacosoma neustria), Dendrolimus Pini, Samatoponia pitiocampa
(Thaumatopoea pityocampa), Atmon Hirozukoga (Phal
era bucePhala), Namish Zifunamishak (Cheimatobia)
brumata), Hibernia defolia
iara), Bupalus piniarus, Hyphantria cunea, Aedes moth (Agr)
otis se getum), Hitenkenmon (Agrotis ypsilo)
n), Spodoptera litura (Barathra brassicae), Red bud (Cirphis unipuncta), Spodoptera litura (Prodenia)
litura), White-spotted armyworm (Laphygma exigua), Panoris flammea (Panolis flammea), Benimon aoringa (Earias insulana), Kingwapa (Plusia gamm)
a), Alabama argillacea, Lymantria dispar, Lymanga
tria monacha), Pieris brassicae,
The white-billed butterfly (Aporia crataegi) belongs to it.

The eyes of the Coleoptera (Coleoptera)
a undata), Melanotus communi
s), Lumonium californicas (Limorius californ)
icus), click beetle (Agriotes lineatus), click beetle (Agriotes obscurus), beetle (Agrilus sinuatu)
s), Maligetes aneneus, Malariathes aneneus, Atomaria linearis, Epilachna varivestria, Phyllopertha horticola, Popillia beetle
japonica), Kofuki Kogane (Melolontha melolontha), Melolontha hippocastani,
Amphimallus solst
itialis), leaf beetle (Crioceris aspargi), leaf beetle (Lama malanopus), leptinotarsa decemlineata, radish beetle (Phaedon cochleariae), flea beetle (Phyllotret)
a memorum), beetle beetle (Chaetocnma tibialis), egg flea beetle (Psylloides chrysocephala), diablochica 12-punctulata (Diabrotica 12-punctala), cassida nebulosa, soybean weevil (Bruchus l)
entis), Vicia weevils (Bru-chus pisorum), Chibico weevil (Sitona lineatus), Otiorrtynchus sulcatus, Otiolinkus
Obata (Otiorrhynchus ovatus), Hylobies abietis, Byctiscus betulae, Ansonoms pomorum
thonomus pomorum), Greater White Finch (Anthonomus g)
randis), green mushroom (Ceuthorrhynchus assimill)
is), Soisorine Kas Napi (Cauthorrhynchus nap
i), Sitophilus granari
a), gypsy moth (Anisandrus dispar), Ips typographus, and Blastophagus piniperda.

In the eyes of the Diptere, Lycoria pectoralis (Lyco
ria pectoralis), Mayetio destructor (Maye
tiola destructor), Japanese larch fly (Dasyneura br)
assicae), fruit fly (Contarinia tritici), rice thrips (Haplodiplosis squstrie), tiprapardosa (T
ipula paludosa), Tipula oleracea
a), fruit fly (Dacus cucurbitae), citrus fruit fly (Dacus
oleae), Ceratitis capita
ta), Rhagoletis cerasi, Rhagoletis pomanella, Anatrepha ludens, Otsucinera
Frit (Oscinella frit)
(Phorbia coaractata), Folbia Antica (Phorb
ia antiqua), box fly moth (Phorbia brasst)
i), Red-legged fly (Pegomya hyoscyami), Anopheles maculipennis, Culex pipiens, Aedes
Aedes aegypti, Aedes vexans, Tabanas bovin
us), Tipula paludosa, Housefly (M)
usca domestica), Fania calculalis (Fannia c)
anicularis), Muscina stab
ulans), Glossina morsitan
s), Oestrus ocis, Chrysomiah
Chrysomya macellaria, Chrysomya hominivorax, Lucilia cuprina, Lucilia sericata
cilia sericata) and Hypoderm lineata
a lineata) belongs.

In the eyes of the Hymenoptera, the wasp (Athalia ro
sae), Haplocampa minuta (Haplocampa minuta), Himeari (Monomorium pharaonis), Solenopsis geminata, Atata texdens
(Atta sex dens) belongs.

In the eyes of Heteroptera, the southern green stink bug (Ne
zara viridula), white stink bug (Eurygaster integr)
iceps), Bilisus leucopteras (Blissus leucopt
erus), Red-billed stink bug (Dysdercus cingulatus), Dysdercus intermedi
us), Piesma quadrata and Lygus pratensis.

In the eyes of the Homoptera, the planthopper (Perkinsiella)
saccaricida), brown planthopper (Nilaparvata lugen)
s), pine tree leafhopper (Empoasca fabae), apple lice (Psyllamali), pear lice (Psylla piri), Trialeurodes vaporarior (Trialeurodes vaporarior)
um), Aphis fabas, apple aphid (Aphis pomi), aphid samouc (Aphis samouc)
i), Aphidula nast
urlaus), Serios gossypi (Cerosipha gossypi)
i), Sappaphis mali, Sappaphis
Mara (Sappaphis mala), pea aphid (Dysaphis radico)
la), Brachycaudus cardu
i), radish aphid (Brevicoryne brassicae), Phlodon humuli, Rhopalomyzus ascalonicus, Myzodes persicae, Myzus c
erasi), Shisaura Korsum pseudo lice (Dysaulaco
rthum pseudosolami), Acyrthosi
phon onobrychis), Macrossiph
on rosae), the broad bean aphid (Megoura vici)
ae), Schizoneura lanuginos
a, Pemphigus bursariu
s), Dreyfusia nordmanni
anae), Dreyfusia piceae, Adelges laricis, and vine aphid (Viteus vitifolii).

In the eyes of the Isoptera, Reticulitermes lucifugus, Carotermes flavicollis, Leukotermis
Flavipes (Leucotermes flavipes) and Termes natalensis belong.

In the eyes of the Orthoptera, Forficula auricularia, Acheta domestica, Gryllotalpa gryllotalpa, Tachycines asynamorus migra, Locca ), Stauronotus maroccanus (Stauronotus maroccanus), Schistocerca peregrina, Nomadacris septemfasciata, Melanoplus spretus, Melanoplus femuru-rubrumur
um), Blata orientalis (Blatta crientalis), German cockroach (Blattella germanica), Periplaneta americana, and Blabera gigantea.

For the mites (Acarina), house dust mites (Ornithonyssus bacot)
i), red spider (Dermanyssus gallinae), red-spotted mite (Orn
ithonyssus sylviarum), fly mite (Macrocheles muscae
domesticae), tsutsugamushi (Trombicula akamushi),
Trombicula scutellaris, Tyrophagus putrescentiae, Sugar mite
yphus lactis), deer mite (Hoshikadania konoi), Dermatophagoides farinae, Dermatophagoides scheremetew-skyi, and other ticks, spider mites, dust mites, lice mites,
It belongs to the mite mites, the mites, the sun mites, the mites, and the mite mites.

As a roundworm, Rhizobium nematode, namely, meloidogyne incognita and meloid papula (M.
hapla), meloidine Japonica (M. javanica), entrapment nematode or Heterodera lostensis (Heterodera
rostochiensis), Heterodera satchi (H. schachti
i), H. avenae, H. giycines, H.
folii), stems and chlorophylls or dithilencus dapushi (D
itylenchus dipsaci), ditilencus destructor
(D.destructor), Pratyrencus Neglectus (Praty
lenchus neglectus), Platylenkas Penetrans
(P.penetrans), Platinumkas Goody (P.goodey)
i), P. curvitaus, P. curvitaus, Tylenchorhynchus dubiu
s), T. claytoni, T. claytoni, Rotylenchus robustus, Heliocotylnchus mul.
ticinctus), Radforus similis (RodophoIus simi)
lis), Peronolimes longi caudatus (Belonolaimu)
s longicaudatus), Longjidras Elongatus (Longi
dorus elongatus), Trichodras Primitives (Tri
chodorus primitivus) belongs.

EXAMPLES In order to explain the present invention in more detail below, Production Examples of the compounds of the present invention will be given as Examples, and then Test Examples will be given.
For reference, Production Examples of 1-citronellyl-5-phenylimidazole are shown as Reference Examples 1 and 2.

Reference Example 1 1-Citronellyl-5-phenylimidazole [general formula (I), ] Into 15 ml of dry dimethylformamide containing 0.01 mol of sodium hydride, an equimolar amount of 4-phenylimidazole is added, and stirred and dissolved at room temperature. After 1 hour, add 0.012 mol of citronellyl mesylate and add 10 more at room temperature.
Continue stirring for hours. Then water is added to the reaction solution and the product is extracted with ether. The ether layer is washed with brine, dried over anhydrous sodium sulfate, the solvent is evaporated under reduced pressure, and the residue is purified by silica gel column chromatography. Elution is carried out first with hexane-ether (2: 1), then with hexane-ether (1: 1) and finally with ether. The isomer of the target substance is eluted with hexane-ether (1: 1), and the target substance is eluted with ether. The solvent is distilled off from the eluate under reduced pressure to obtain the title compound. Yield 4% Elemental analysis value (as C ₁₉ H ₂₆ N ₂ ) Ultraviolet absorption spectrum (UV) analysis result λ _max (CH ₃ OH) = 250 nm (ε = 10800) Nuclear magnetic resonance spectrum ( ¹ H-NMR) analysis result In CDCl ₃ , TMS was used as an internal standard substance. Shown in the figure.

Reference Example 2 1-Citronellyl-5-phenylimidazole (general formula (1), ] 0.007 mol of citronellylamine and benzaldehyde
0.007 mol is dissolved in dichloromethane and heated under reflux for 3 hours in the presence of 0.3 mol of anhydrous magnesium sulfate. After removing magnesium sulfate, the solution is concentrated under reduced pressure. The obtained imine compound is dissolved in dry methanol, 0.02 mol of anhydrous potassium carbonate is added to the solution, and then 0.01 mol of p-toluenesulfonylmethyl isocyanide (TosMIC) is slowly added thereto, followed by stirring at room temperature for 1 day. The solvent is distilled off from the reaction mixture under reduced pressure, and the residue is extracted with ether. The ether layer is washed with brine, dried over anhydrous sodium sulfate, the solvent is distilled off under reduced pressure, and the residue is purified by silica gel column chromatography. Elution is carried out first with hexane-ether (2: 1) and subsequently with ether. The target product is eluted with ether, and the solvent is distilled off from the solution under reduced pressure to obtain the title compound. Yield 12% ¹ H-NMR analysis result (CDCl ₃ , TMS): As shown in FIG. 2, it was completely in agreement with FIG. 1 (that of the compound obtained in Example 1).

Example 1 1-Citronellyl-5- (4-chlorophenyl) imidazole [general formula (I), ] The title compound is obtained by the same operation as in Example 1 using 4-p-chlorophenylimidazole instead of 4-phenylimidazole.

Yield 3.1% ¹ H-NMR analysis result (CDCl ₃ , TMS): Shown in FIG.

The title compound is also produced by the same procedure as in Reference Example 2.

Example 2 1-Citronellyl-5- (4-fluorophenyl) imidazole [general formula (I), ] The title compound is obtained by performing the same operation as in Reference Example 1 using 4-p-fluorophenylimidazole instead of 4-phenylimidazole.

Yield 2.1% ¹ H-NMR analysis result (CDCl ₃ , TMS): Shown in FIG.

The title compound is also produced by the same procedure as in Reference Example 2.

Example 3 1-citronellyl-5- (4-methoxyphenyl) imidazole [general formula (I), ] The title compound is obtained by substituting p-anisaldehyde for benzaldehyde and performing the same operation as in Reference Example 2. Yield 22% ¹ H-NMR analysis result (CDCl ₃ , TMS): Shown in FIG.

Example 4 1-Citronellyl-5- (3,4-methylenedioxyphenyl) imidazole [general formula (I), ] The title compound is obtained by performing the same operation as in Reference Example 2 using 3,4-methylenedioxybenzaldehyde instead of benzaldehyde. Yield 13% ¹ H-NMR analysis result (CDCl ₃ , TMS): Shown in FIG.

Example 5 1-citronellyl-5- (2-chlorophenyl) imidazole [general formula (I), ] The title compound is obtained by substituting 2-chlorobenzaldehyde for benzaldehyde and performing the same operation as in Reference Example 2. Yield 3% ¹ H-NMR analysis result (CDCl ₃ , TMS): Shown in FIG. 7.

Example 6 1-Citronellyl-5- (3-chlorophenyl) imidazole [general formula (I), ] The title compound is obtained by substituting 3-chlorobenzaldehyde for benzaldehyde and performing the same operation as in Reference Example 2. Yield 2.5% ¹ H-NMR analysis result (CDCl ₃ , TMS): Shown in FIG.

Example 7 1-Citronellyl-5- (2-methoxyphenyl) imidazole [general formula (I), ] The title compound is obtained by the same operation as in Reference Example 2 using O-methoxybenzaldehyde instead of benzaldehyde. Yield 31% ¹ H-NMR analysis result (CDCl ₃ , TMS): Shown in FIG. 9.

Example 8 1-Citronellyl-5- (2-ethoxyphenyl) imidazole [general formula (I), ] The title compound is obtained by substituting O-ethoxybenzaldehyde for benzaldehyde and performing the same operation as in Example 2. Yield 27% ¹ H-NMR analysis result (CDCl ₃ , TMS): Shown in FIG.

Example 9 1-Citronellyl-5- (2,4-dimethoxyphenyl) imidazole [general formula (I), ] The title compound is obtained by performing the same operation as in Reference Example 2 using 2,4-dimethoxybenzaldehyde instead of benzaldehyde. Yield 36% ¹ H-NMR analysis result (CDCl ₃ , TMS): Shown in FIG. 11.

Example 10 1-Citronellyl-5- (2,4-dichlorophenyl) imidazole [general formula (I), ] The same operation as in Reference Example 2 was carried out by using 2,4-dichlorobenzaldehyde instead of benzaldehyde.
Obtain the title compound. Yield 1.4% ¹ H-NMR analysis result (CDCl ₃ , TMS): Shown in FIG.

[Anti-JH activity test]

A compound of the present invention diluted to a predetermined concentration with acetone in a 3rd or 4th instar silkworm larva (each within 0 to 8 hours after molting) of a domesticated silkworm (Bombyx mori) fed with mulberry leaves ) Was applied to 1 to 4 μl per individual and dropped on the back of the abdomen. Immediately after the treatment, each larva was transferred to a plastic case and fed with mulberry leaves and bred until cocooning. The anti-JH activity was evaluated by the appearance rate (%) of individuals (precocious larvae) that started cocooning at the 4th instar larva stage without undergoing the 5th instar molting. The number of test individuals for each reagent solution was 20. Further, all the control plots in which acetone was used in place of the reagent solution were cocooned after molting at the 5th instar.

The results for the 3rd instar silkworm larvae are shown in Table 1 below, and the results for the 4th instar silkworm larvae are shown in Table 2 below.

From Tables 1 and 2 above, the compounds of the present invention are generally anti-J
It has H activity, and in particular, the compounds obtained in Examples 2, 3, 5 and 6 are found to have strong anti-JH activity.

[Brief description of drawings]

1 and 2 are nuclear magnetic resonance spectrum analysis diagrams of the compounds obtained in Reference Examples 1 and 2, and FIGS. 3 to 12 are nuclear magnetic resonance spectrum analysis diagrams of the compound of the present invention, respectively.

Claims (4)

[Claims] 1. A general formula [In the formula, R represents a phenyl group having a halogen atom, a lower alkoxy group or a methylenedioxy group as a substituent. ] 1-Citronellyl-5-substituted imidazoles represented by: 2. General formula [In the formula, R represents a phenyl group having a halogen atom, a lower alkoxy group or a methylenedioxy group as a substituent. ] The imidazole compound represented by [Wherein R'represents a mesyloxy group or a halogen atom.] A general formula characterized by reacting with a citronellol derivative represented by [Wherein R is the same as above. ] The manufacturing method of 1-citronellyl-5-substituted imidazole represented by these. 3. General formula [In the formula, R represents a phenyl group having a halogen atom, a lower alkoxy group or a methylenedioxy group as a substituent. ] The general formula characterized by reacting an imine compound represented by: with tosylmethyl isocyanide [Wherein R is the same as above. ] The manufacturing method of 1-citronellyl-5-substituted imidazole represented by these. 4. A general formula [In the formula, R represents a phenyl group having a halogen atom, a lower alkoxy group or a methylenedioxy group as a substituent. ] The anti-juvenile hormone activator containing the 1-citronellyl-5-substituted imidazole represented by the following as an active ingredient.