Dihalopropene compounds, insecticides containing them as active

Details Dihalopropene compounds, insecticides containing them as active Dihalopropene compounds, insecticides containing them as active

1997-09-24

1999-09-14

Kumar, Shailendra

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Nitrogen containing other than solely as a nitrogen in an...

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Patent

active

059523867

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD

The present invention relates to dihalopropene compounds, insecticides containing them as active ingredients, and intermediates for their production.


BACKGROUND ART

As disclosed in JP-A48-86835/1973 and JP-A 49-1526/1974, for example, it is well known that some kinds of propene compounds can be used as active ingredients of insecticides.
In view of their insecticidal activity, however, it cannot always be said that these compounds are satisfactorily effective for the control of noxious insects.


DISCLOSURE OF INVENTION

The present inventors have intensively studied to find a compound having excellent insecticidal activity. As a result, they have found that particular dihalopropene compounds have satisfactory insecticidal activity for the control of noxious insects, thereby completing the present invention.
That is, the present invention provides dihalopropene compounds of the general formula: ##STR2## wherein m is an integer of 0 to 4; -C.sub.3 alkyl; haloalkyl or C.sub.1 -C.sub.3 alkyl; alkyl or trifluoromethyl; NR.sub.13 SO.sub.2, NR.sub.13 C(.dbd.W.sub.1)--W, WC(.dbd.W.sub.1)NR.sub.13 or NR.sub.14 C(.dbd.W)NR.sub.13 in which W and W.sub.1 are independently oxygen or sulfur, and R.sub.13 and R.sub.14 are independently hydrogen, C.sub.1 -C.sub.10 alkyl, C.sub.1 -C.sub.5 haloalkyl, C.sub.2 -C.sub.10 alkenyl, C.sub.2 -C.sub.6 haloalkenyl, C.sub.3 -C.sub.9 alkynyl or C.sub.3 -C.sub.5 haloalkynyl; -C.sub.10 alkenyl, C.sub.2 -C.sub.6 haloalkenyl, C.sub.3 -C.sub.9 alkynyl, C.sub.3 -C.sub.5 haloalkynyl, C.sub.2 -C.sub.7 alkoxyalkyl, C.sub.2 -C.sub.7 alkylthioalkyl, alkyl, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.3 haloalkoxy, -C.sub.4 alkyl, alkyl, C.sub.6 -C.sub.8 cycloalkenylalkyl optionally substituted with C.sub.1 -C.sub.4 alkyl, Q.sub.4 of the general formula: ##STR3## in which M is oxygen, NH or sulfur, -C.sub.8 alkyl, C.sub.1 -C.sub.3 haloalkyl, C.sub.1 -C.sub.7 alkoxy, C.sub.1 -C.sub.3 haloalkoxy, C.sub.1 -C.sub.3 alkylthio, C.sub.1 -C.sub.3 haloalkylthio, C.sub.3 -C.sub.6 alkenyloxy, C.sub.3 -C.sub.6 haloalkenyloxy, C.sub.1 -C.sub.3 hydroxyalkyl, C.sub.2 -C.sub.4 alkenyl, C.sub.2 -C.sub.4 haloalkenyl, C.sub.2 -C.sub.4 alkynyl, C.sub.2 -C.sub.4 alkynyloxy, C.sub.2 -C.sub.4 haloalkynyl, C.sub.2 -C.sub.4 haloalkynyloxy, C.sub.2 -C.sub.4 alkoxyalkyl, C.sub.2 -C.sub.4 alkylthioalkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.5 -C.sub.6 cycloalkenyl, C.sub.2 -C.sub.5 alkoxycarbonyl, C.sub.3 -C.sub.6 cycloalkyloxy, C.sub.5 -C.sub.6 cycloalkenyloxy, -C.sub.3 haloalkyl, C.sub.1 -C.sub.3 alkoxy or C.sub.1 -C.sub.3 haloalkoxy, phenoxy optionally substituted with halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.3 haloalkyl, C.sub.1 -C.sub.3 alkoxy or C.sub.1 -C.sub.3 haloalkoxy, -C.sub.3 haloalkyl, C.sub.1 -C.sub.3 alkoxy or C.sub.1 -C.sub.3 haloalkoxy, C.sub.1 -C.sub.3 haloalkyl, C.sub.1 -C.sub.3 alkoxy or C.sub.1 -C.sub.3 haloalkoxy; together at their ends to form trimethylene or tetramethylene, methylenedioxy optionally substituted with halogen or C.sub.1 -C.sub.3 alkyl, or ethylenedioxy optionally substituted with halogen or C.sub.1 -C.sub.3 alkyl; and -C.sub.3 alkyl or trifluoromethyl.
The present invention further provides compounds of the general formula: ##STR4## which are useful as intermediates for the production of some of the present compounds, wherein X's are independently chlorine or bromine; R.sub.18 and R.sub.19 are independently halogen or C.sub.1 -C.sub.3 alkyl; R.sub.17 is amino or carboxyl; R.sub.5, R.sub.6 and R.sub.7 are independently hydrogen, C.sub.1 -C.sub.3 alkyl or trifluoromethyl; and m is an integer of 0 to 4. More particularly, the present invention provides phenol compounds of the general formula: ##STR5## wherein R.sub.20 is Q.sub.1 as defined above, or 2-pyridyl, 2-pyrazinyl, 2-indolyl, 2-pyrrolyl, 2-quinolyl, 2-thienyl, 3-thienyl, 2-furyl, 3-furyl, 3-pyridyl or 4-pyridyl, each of which may be optionally substituted with (R.sub.16).sub.s in which R.sub.16 is halogen, nitro, cyano, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.3 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.

REFERENCES:
patent: 5530015 (1996-06-01), Sakamoto et al.

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