Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1996-12-12
1997-11-04
Powers, Fiona T.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
514340, 514341, 514359, 514406, 546261, 5462681, 5462754, 546300, 546302, 548255, 5483641, 5483657, 5483751, 5483761, A01N 4356, C07D21364, C07D23112, C07D23116, C07D24904
Patent
active
056840225
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/JP95/00664 filed Apr. 6, 1995.
TECHNICAL FIELD
The present invention relates to ether compounds, their use, and intermediates for use in their production. More particularly, the present invention relates to ether compounds which have excellent controlling effects against harmful organisms, harmful-organism controlling agents containing them as active ingredients, and intermediates for use in the production of these ether compounds.
DISCLOSURE OF THE INVENTION
The present inventors have intensively studied to find compounds which have excellent controlling effects against harmful organisms. As a result, they have found that ether compounds of the general formula P-1 as depicted below have excellent controlling effects against harmful organisms, thereby completing the present invention.
Thus the present invention provides ether compounds (hereinafter referred to as the present compound(s)) of the general formula: ##STR3## wherein R.sup.1 is halogen; ##STR4##
R.sup.2, R.sup.3, R.sup.4 and R.sup.7 are inependently hydrogen or methyl;
R.sup.5 and R.sup.8 are independently C.sub.1 -C.sub.4 alkyl (optionally substituted with halogen or methoxy), C.sub.3 -C.sub.4 alkenyl (optionally substituted with halogen) or C.sub.3 -C.sub.4 alkynyl (optionally substituted with halogen);
R.sup.6 is a group represented by R.sup.5, or hydrogen;
R.sup.9 is halogen or C.sub.1 -C.sub.4 alkyl (optionally substituted with halogen);
R.sup.10 and R.sup.11 are independently hydrogen, C.sub.1 -C.sub.4 alkyl or C.sub.3 -C.sub.4 alkenyl;
B is a group of the general formula: ##STR5##
E is a group of the general formula: ##STR6##
R.sup.12 is halogen, or methyl optionally substituted with halogen;
X and Y are independently oxygen or sulfur;
W is oxygen, sulfur or NH; and
l, m and n are independently an integer of 0 to 2; and harmful-organism controlling agents containing them as active ingredients.
The present invention further provides a phenol compound of the general formula: ##STR7## wherein E is as defined above, which is useful as an intermediate for use in the production of the above ether compound.
The present compounds have excellent juvenile hormone-like activity particularly against insects, i.e., they have functions such as inhibition of metamorphosis into adults, inhibition of embryogenesis and sterilization of adults. For this reason, the present compounds may serve generally as growth regulators, chemosterilants, ovicides or reproduction inhibitors to produce high controlling effects against various noxious insects, including those having an increased resistance to the existing insecticides, such as those which are found in agriculture, forestry and horticulture; those which infest stored grains; and those which are detrimental to health.
EMBODIMENTS FOR MAKING THE INVENTION
The present compounds are represented by the above general formula P-1.
As the halogen represented by R.sup.1, R.sup.9 and R.sup.12, there can be mentioned fluorine, chlorine, bromine or iodine.
As the C.sub.1 -C.sub.4 alkyl (optionally substituted with halogen or methoxy group) represented by R.sup.5, R.sup.6 and R.sup.8, there can be mentioned, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, 2,2,2-trifluoroethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2,2,3,3,3-pentafluoropropyl, methoxyethyl and 3-methoxypropyl.
As the C.sub.3 -C.sub.4 alkenyl (optionally substituted with halogen) represented by R.sup.5, R.sup.6 and R.sup.8, there can be mentioned, for example, allyl, 2-methylallyl, 2-butenyl, 1-methylallyl, 2-chloroallyl and 3,3-dichloroallyl.
As the C.sub.3 -C.sub.4 alkynyl (optionally substituted with halogen) represented by R.sup.5, R.sup.6 and R.sup.8, there can be mentioned, for example, propargyl, 2-butynyl, 4,4,4-tri-fluoro-2-butynyl.
As the C.sub.1 -C.sub.4 alkyl (optionally substituted with halogen) represented by R.sup.9, there can be mentioned, for example, methyl, ethyl, n-propyl, isopropyl, sec-butyl, isobutyl, tert-butyl, trifluoromethyl and 2,2,2-trifluoroethyl.
A
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Fujimoto Hiroaki
Kisida Hirosi
Shuto Akira
Takada Yoji
Tsuchiya Toru
Powers Fiona T.
Sumitomo Chemical Company Limited
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