Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1987-11-23
1989-03-14
Schwartz, Richard A.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
548335, 548346, A61K 31415, C07D23358
Patent
active
048124737
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to 1,5-disubstituted imidazoles and salts thereof, a process for their preparation and an agent having an activity to be effective against the juvenile hormone.
BACKGROUND ART
The growth and reproduction of arthropods such as insects and the like are controlled by their hormones. For example, chiefly their two hormones, i.e., juvenile hormone (JH) and moulting hormone (MH), participate in the ecdysis and metamorphosis of larvae during their growth. If the relative balance of these hormones in insects' living body could be disturbed, the insects' normal development could be retarded. Accordingly if this action is utilized, noxious insects to be controlled could be selectively killed without affecting humans and other animals. From this viewpoint, these hormones and susbstances having similar activities have been variously investigated and developed as a new low-toxicity vermin-repellent or -killing agent and are attracting attention. Said JH is a hormone related to, e.g. insects' development, reproduction and dormancy. For example, it is known that the larvae from which the corpus allatum capable of secreting the juvenile hormone has been removed become a pupa or imago without undergoing repeated normal ecdysis (premature metamorphosis). If a substance having an action to inhibit the activity of the juvenile hormone (anti-JH active substance) is discovered, the substance could similarly suppress the larva's normal growth, cause the larva's premature metamorphosis, damage the imago's reproductive function and exhibit an ovicidal activity. Since the premature metamorphosis thus occurring results in small-size larvae and in the reduction of larval period, the extent of damage inflicted by the larvae of noxious insects on agricultural products will be diminished and the number of noxious insects will be decreased.
OBJECT OF THE INVENTION
From such viewpoints, the present inventors conducted extensive research to provide an anti-JH active substance which can be used as a new hormone-type vermin-repellent or -killing agent and successfully synthesized 1,5-disubstituted imidazoles represented by the formula (A) shown below to find that these compounds and salts thereof can fulfill said object. Based on this finding, the inventors have accomplished an invention, which was then applied for a patent (Patent Application No. Showa 59-186015). ##STR2## wherein R.sup.a is a citronellyl group or a phenyl lower alkyl group optionally having on the phenyl ring a halogen atom, a lower alkyl group or a lower alkoxy group as a substituent, and R.sup.b is a 2,6-dimethyl-1,5-heptadienyl group, a phenyl group or a styryl group, with the proviso that when R.sup.a is a citronellyl group, R.sup.b must not be a phenyl group.
CONSTRUCTION OF THE INVENTION
As a result of continued research, the inventors have accomplished the present invention which concerns with 1,5-disubstituted imidazoles of the formula (1) as shown below and salts thereof, a process for their preparation and an agent containing the compound and having an activity to be effective against the juvenile hormone. ##STR3##
wherein R.sup.1 is a lower alkyl group, a cycloalkyl group or a phenyl lower alkyl group, and R.sup.2 is a 2,6-dimethyl-1,5-heptadienyl group or a 2,6-dimethylheptyl group, except for a compound wherein R.sup.1 is a phenyl lower alkyl group and R.sup.2 is a 2,6-dimethyl-1,5-heptadienyl group.
The term "lower alkyl group" used herein refers to a straight chain or branched chain alkyl group having 1 to 6 carbon atoms. Examples of the lower alkyl group are methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, amyl, isoamyl, hexyl and the like. The phenyl lower alkyl groups include those with the alkyl moeity which is a straight chain or branched chain alkyl group having 1 to 6 carbon atoms such as benzyl, phenethyl, phenylpropyl, phenylbutyl, phenylhexyl and the like. The term "cycloalkyl group" is intended to denote the cycloalkyl groups having 3 to 8 carbon atoms among which a c
REFERENCES:
Kuwano, E. et al., Agric. Biol. Chem., 49(2), 483-486 (1985).
Asano Shoji
Eto Morifusa
Kuwano Eiichi
Takeya Ryuko
Earth Chemical Co., Ltd.
Schwartz Richard A.
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