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US 4,426,385 AGranted
Insecticidal bicyclooxyphenyl ureas
AssigneeUnion Carbide Corporation
InventorPaul A. Cain
Life of this patent
Estimating the term…
Abstract
Novel bicyclooxyphenyl ureas, such as 1-(bicyclooxyphenyl)-benzoyl ureas, are provided which exhibit pesticidal activity. The compositions are conveniently prepared by reacting an isocyanate with either an amide or a bicyclooxyaniline.
Claims84
A composition of the formula:
- ##STR28## wherein M represents a monocyclic aromatic ring system or a monocyclic heterocyclic ring system containing up to 2 nitrogen atoms, and wherein the ring can contain up to four X substituents wherein each X individually can be halogen, nitro, cyano, or alkyl, polyhaloalkyl, alkoxy or polyhaloalkoxy of from 1 to 3 carbon atoms;
- Z and Z.sup.1 individually are hydrogen or alkyl of from 1 to 8 carbon atoms, or alkyl of from 1 to 8 carbon atoms which is substituted with at least one of halogen, hydroxyl or alkoxy;
- Y individually represents halogen, or alkyl, polyhaloalkyl, alkoxy or polyhaloalkoxy of from 1 to 3 carbon atoms, and n has a value of from 0 to 4;
- B is a bicyclic fused ring system which is attached to the oxygen through a carbocyclic ring and wherein (a) at least one ring is a six-membered, unsaturated carbocyclic ring which can contain up to two R and R.sup.1 substituents wherein R and R.sup.1 can be halogen, nitro, cyano, amino, formamido, formamidino, phenylsulfenyl, phenylsulfinyl, phenylsulfonyl, phenylsulfamido wherein the phenyl ring optionally may be substituted with one or more halogen, nitro, or alkyl, polyhaloalkyl, alkoxy or polyhaloalkoxy of from 1 to 3 carbon atoms, or R and R.sup.1 individually are alkyl, alkoxy, polyhaloalkyl, polyhaloalkoxy, alkenyloxy, polyhaloalkenyloxy, alkynyloxy, polyhaloalkynyloxy, alkylsulfenyl, poyhaloalkylsulfenyl, alkylsulfinyl, polyhaloalkylsulfinyl, alkylsulfonyl, polyhaloalkylsulfonyl, mono- or di-alkylsulfamido, mono- or di-alkylamino, alkylcarbonylamino, alkoxycarbonylamino, mono- or di-alkylaminocarbonyloxy of up to 6 carbon atoms, and (b) the second ring, hereinafter also referred to as A, when it is not a five or six-membered carbocyclic can be a five or six-membered saturated or unsaturated hetero-cyclic ring which can contain in any combination carbonyl or one or two oxygen or sulfur, and up to two R.sup.2 and R.sup.3 substituents attached to unsaturated ring carbon atoms wherein R.sup.2 and R.sup.3 individually can be halogen, nitro, cyano, or alkyl, polyhaloalkyl, alkoxy, polyhaloalkoxy, alkylthio, arylthio, alkylsulfinyl, arylsulfinyl, alkylsulfonyl, arylsulfonyl, alkylsulfamido, arylsulfamido, alkoxycarbonylamino, or alkylcarbonylamino of from 1 to 6 carbon atoms, or can contain up to two R.sup.4 and R.sup.5 substituents attached to saturated carbon atoms of the chain wherein R.sup.4 and R.sup.5 individually can be alkyl or polyhaloalkyl of from 1 to 6 carbon atoms;
- with the proviso that when B is a naphthyl group it is attached through an oxygen to the number 4 carbon atom of the phenyl group, and with the further proviso that (a) if X is halogen and is mono or disubstituted in the ortho position of a benzoyl ring (b) if Z and Z.sup.1, are hydrogen (c) if no more than 2 of R, R.sup.1, R.sup.2 or R.sup.3 are hydrogen, chloro or bromo, and (d) if Y represents chloro, then n has a value of at least 2.
2 more elements
A composition of the formula:
- ##STR36## wherein R is chloro, alkoxy or dialkylamino of from 1 to 6 carbon atoms, X is chloro or fluoro, X.sup.1 is hydrogen, chloro or fluoro, Y is hydrogen, chloro, bromo, methyl or methoxy, Y.sup.1 and Y.sup.2 independently are hydrogen, chloro, bromo or methyl with the proviso that if Y.sup.1 and Y.sup.2 are hydrogen and if R is chloro then Y can not be hydrogen or chloro.
A composition of the formula:
- ##STR37## wherein R is chloro, or dialkylamine of 1 to 6 carbon atoms, X is hydrogen, chloro or fluoro, X.sup.1 is chloro or fluoro, Y is hydrogen chloro, bromo, methyl or methoxy, Y.sup.1 and Y.sup.2 independently are hydrogen, chloro, bromo or methyl.
A composition of the formula:
- ##STR38## wherein X is chloro or fluoro, X.sup.1 is hydrogen, chloro or fluoro and Y is hydrogen or chloro.
A composition of the formula:
- ##STR39## wherein X is chloro or fluoro, X.sup.1 is hydrogen, chloro or fluoro, Y is chloro, bromo or methyl.
A composition of the formula:
- ##STR40## wherein X is chloro or fluoro, X.sup.1 is hydrogen, chloro or fluoro and Y is chloro or methyl.
A composition of the formula:
- ##STR41## wherein X is chloro or fluoro, X.sup.1 is hydrogen, chloro or fluoro and R is chloro or methoxy.
A composition of the formula:
- ##STR42## wherein X is chloro or fluoro, X.sup.1 is hydrogen, chloro or fluoro and Y is chloro or methyl.
A composition of the formula:
- ##STR43## wherein X is chloro or fluoro and X.sup.1 is hydrogen, chloro or fluoro.
A composition of the formula:
- ##STR44## wherein X is chloro or fluoro, X.sup.1 is hydrogen, chloro or fluoro, Y is chloro, methyl or methoxy, and R is chloro or dimethylamino.
A composition of the formula:
- ##STR45## wherein X is chloro or fluoro, X.sup.1 is hydrogen, chloro or fluoro, Y and Y.sup.1 are chloro, bromo or methyl or a combination of chloro and methyl.
A composition of the formula:
- ##STR46## wherein X is chloro or fluoro, X.sup.1 is hydrogen, chlor or fluoro and Y is chloro or methyl.
A composition of the formula:
- ##STR47## wherein X is chloro or fluoro, X.sup.1 is hydrogen, chloro or fluoro and R is chloro or dimethylamino.
Dependencies are inferred from the claim text.