4, 5-dihydropyrazole-5-thione derivatives and miticides comprisi

Details 4, 5-dihydropyrazole-5-thione derivatives and miticides comprisi 4, 5-dihydropyrazole-5-thione derivatives and miticides comprisi

1996-09-11

1997-06-17

Ramsuer, Robert W.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

5462761, 5483661, 5483704, 5483717, 5483575, A01N 4340, A01N 4356, C07D23118, C07D40104

Patent

active

056397763

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD

The present invention relates to novel 4, 5-dihydropyrazole-5-thione derivatives and to miticides comprising the same.


PRIOR ART

Of dihydropyrazolone derivatives, some are known as bioactive compounds, and several publications disclose such bioactivity of the compounds. For example, EP patent specification No. 23636 discloses compounds which exert insecticidal activity and Japanese Unexamined Patent Publication No. 213892/1993 discloses compounds which exert herbicidal activity. However, there has been no disclosure that 4, 5-dihydropyrazole-5-thione derivatives have bioactivity applicable to agriculture.


DISCLOSURE OF THE INVENTION

In view of the foregoing, the inventors conducted extensive research on dihydropyrazolone derivatives to develop compounds which exhibit excellent bioactivity applicable to agriculture and found that 4, 5-dihydropyrazole-5-thione derivatives represented by the following general formula (1) are novel compounds undisclosed in the publications and that although 4, 5-dihydropyrazol-5-one derivatives which are intermediates for synthesizing 4, 5-dihydropyrazole-5-thione derivatives do not have miticidal activity, 4, 5-dihydropyrazole-5-thione derivatives represented by the following general formula (1) have remarkably potent miticidal activity against various kinds of spider mites which adversely affect agriculture. The present invention was accomplished based on the above-mentioned findings.
In accordance with the present invention, there are provided a 4, 5-dihydropyrazole-5-thione derivative represented by the following general formula (1) and a miticide comprising the derivative as an active ingredient ##STR2## wherein R.sup.1 represents a straight- or branched-chain alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a lower alkenyl group, a lower alkynyl group, a benzyl group which may have substituents, a phenylcarbonyl lower alkyl group, a lower alkylcarbonyl lower alkyl group, a group ##STR3## or a group ##STR4## in which Y represents a halogen atom, a lower alkyl group, a lower alkoxy group, a lower haloalkyl group, a lower haloalkoxy group, a lower alkoxycarbonyl group, a phenoxy group which may have substituents, a phenyl group which may have substituents, an amino group, a cyano group or a nitro group; m is 0 or an integer of 1 to 3; R.sup.4 represents a lower alkyl group; p is 0, 1 or 2; R.sup.5 and R.sup.6 are the same or different and represent a hydrogen atom or a lower alkyl group; R.sup.2 and R.sup.3 are the same or different and represent a lower alkyl group or a cycloalkyl group having 3 to 8 carbon atoms, or R.sup.2 and R.sup.3 may be combined to form a cycloalkyl ring having 3 to 8 carbon atoms; X represents a halogen atom, a lower alkyl group, a lower alkoxy group, a lower haloalkyl group, a lower haloalkoxy group, a lower alkoxycarbonyl group, a phenoxy group which may have substituents, a phenyl group which may have substituents, a cyano group, an amino group or a nitro group; n is 0 or an integer of 1 to 3; A represents .paren open-st.C=) or .paren open-st.N=) ; the substituent contained in the abovementioned benzyl group, phenoxy group and phenyl group which may have substituents is at least one group selected from the group consisting of a halogen atom, a lower alkyl group, a lower alkoxy group, a lower haloalkyl group, a nitro group, a cyano group and a lower alkoxycarbonyl group.
The groups represented by R.sup.1, R.sup.2, R.sup.3 and X are explained in more detail below.
As a straight- or branched-chain alkyl group having 1 to 12 carbon atoms, a straight- or branched-chain alkyl group having 1 to 6 carbon atoms such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, n-pentyl, n-hexyl or the like, and besides, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl and the like are mentioned.
As a cycloalkyl group having 3 to 8 carbon atoms, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl and the like are mentioned.
As a lower alkenyl group, a str

REFERENCES:
Maquestiau et al, Chemical Abstracts, vol. 87 No. 2313q (1977).
la Cour et al, Chemical Abstracts, vol. 118 No. 138575 (1993).

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