US 4,289,778 AGranted

2-(Substituted imino)-N-(3-substituted phenyl)-3-thiazolidinecarbothioamides

AssigneeEli Lilly and Company

InventorTerry W. Balko

Life of this patent

Estimating the term…

Abstract

2-(Substituted imino)-N-(3-substituted phenyl)-3-thiazolidinecarbothioamides, useful as insecticides.

Claims97

Dependent claims

A compound of the formula, ##STR5## wherein R.sup.1 represents

(A) C.sub.1 -C.sub.18 alkyl;
(B) C.sub.2 -C.sub.18 alkenyl;
(C) C.sub.4 -C.sub.18 alkadienyl;
(D) C.sub.3 -C.sub.12 cycloalkyl, optionally substituted with either one or two C.sub.1 -C.sub.4 alkyl groups;
(E) C.sub.5 -C.sub.12 cycloalkenyl, optionally substituted with either one or two C.sub.1 -C.sub.3 alkyl groups;
(F) C.sub.6 -C.sub.12 cycloalkadienyl, optionally substituted with either one or two C.sub.1 -C.sub.3 alkyl groups;
(G) phenyl, optionally substituted with from one to three groups selected from the group consisting of
(1) C.sub.1 -C.sub.6 alkyl,
(2) C.sub.1 -C.sub.6 alkoxy,
(3) C.sub.1 -C.sub.6 alkylthio,
(4) trifluoromethyl,
(5) halo, and
(6) cyano;
(H) (cycloalkyl)alkyl, containing no more than about 18 carbon atoms, in which the cycloalkyl moiety is as defined herein above;
(I) phenylalkyl, containing no more than about 18 carbon atoms, in which the phenyl moiety is as defined hereinabove;
(J) diphenylalkyl, containing no more than about 18 carbon atoms, in which each phenyl moiety is as defined hereinabove;
(K) pyridyl, optionally substituted with either one or two groups selected from the group consisting of
(1) C.sub.1 -C.sub.3 alkyl,
(2) C.sub.1 -C.sub.3 alkoxy, or
(3) halo;
(L) piperidino, optionally substituted with either one or two C.sub.1 -C.sub.3 alkyl groups;
(M) morpholino;
(N) pyrazinyl, optionally substituted with either one or two C.sub.1 -C.sub.3 alkyl groups;
(O) pyridylalkyl, containing no more than about 17 carbon atoms, in which the pyridyl moiety is as defined hereinabove;
(P) piperidinoalkyl, containing no more than about 17 carbon atoms, in which the piperidino moiety is as defined hereinabove;
(Q) morpholinoalkyl, containing no more than about 16 carbon atoms;
(R) pyrazinylalkyl, containing no more than about 16 carbon atoms, in which the pyrazinyl moiety is as defined hereinabove;
(S) tetrahydrofurylalkyl, containing no more than about 17 carbon atoms;
and
(T) substituted amino, having the formula ##STR6## in which R.sup.8 and R.sup.9 independently are selected from the group consisting of hydrogen, C.sub.1 -C.sub.18 alkyl, phenyl, and phenylalkyl, wherein the phenyl and phenylalkyl moieties are as defined hereinabove, provided that at least one of R.sup.8 and R.sup.9 is other than hydrogen;
R.sup.2 and R.sup.3 independently are selected from the group consisting of
(A) hydrogen,
(B) C.sub.1 -C.sub.3 alkyl, and
(C) phenyl, with the proviso that when one of R.sup.2 and R.sup.3 is phenyl, the other of R.sup.2 and R.sup.3 is hydrogen;
R.sup.4 represents
(A) hydrogen or
(B) C.sub.1 -C.sub.3 alkyl;
R.sup.5 represents
(A) halo,
(B) trifluoromethyl,
(C) cyano, or
(D) 1,1,2,2-tetrafluoroethoxy;
and
R.sup.6 represents
(A) hydrogen,
(B) halo, or
(C) C.sub.1 -C.sub.3 alkyl;
with the provisos that when R.sup.5 is bromo, R.sup.1 can not be 3-bromophenyl;
when R.sup.5 is cyano, R.sup.1 can not be 3-cyanophenyl;
when R.sup.5 is halo and R.sup.6 is halo, R.sup.6 can not be in the 2-position;
and when R.sup.5 is halo and R.sup.6 is C.sub.1 -C.sub.3 alkyl, R.sup.6 can not be in the 4-position.

48 more elements

Dependencies are inferred from the claim text.

Facts

Application: 05/864,998Filed 27 Dec 1977
Granted: 15 Sep 1981
Term ends: Not estimatedThe source records don’t support an estimate.

Classification9 codes

C07D 417/12
Containing two hetero rings: linked by a chain containing hetero atoms as chain links
A01N 47/38
Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<: containing the group >N—CO—N< where at least one nitrogen atom is part of a…
C07D 233/48
Nitrogen atoms not forming part of a nitro radical: with acyclic hydrocarbon or substituted acyclic hydrocarbon radicals, attached to said…
C07D 233/50
Nitrogen atoms not forming part of a nitro radical: with carbocyclic radicals directly attached to said nitrogen atoms

Family

No related US applications are recorded in the indexed filing history.

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Citations

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A compound of the formula, ##STR5## wherein R.sup.1 represents

(A) C.sub.1 -C.sub.18 alkyl;
(B) C.sub.2 -C.sub.18 alkenyl;
(C) C.sub.4 -C.sub.18 alkadienyl;
(D) C.sub.3 -C.sub.12 cycloalkyl, optionally substituted with either one or two C.sub.1 -C.sub.4 alkyl groups;
(E) C.sub.5 -C.sub.12 cycloalkenyl, optionally substituted with either one or two C.sub.1 -C.sub.3 alkyl groups;
(F) C.sub.6 -C.sub.12 cycloalkadienyl, optionally substituted with either one or two C.sub.1 -C.sub.3 alkyl groups;
(G) phenyl, optionally substituted with from one to three groups selected from the group consisting of
(1) C.sub.1 -C.sub.6 alkyl,
(2) C.sub.1 -C.sub.6 alkoxy,
(3) C.sub.1 -C.sub.6 alkylthio,
(4) trifluoromethyl,
(5) halo, and
(6) cyano;
(H) (cycloalkyl)alkyl, containing no more than about 18 carbon atoms, in which the cycloalkyl moiety is as defined herein above;
(I) phenylalkyl, containing no more than about 18 carbon atoms, in which the phenyl moiety is as defined hereinabove;
(J) diphenylalkyl, containing no more than about 18 carbon atoms, in which each phenyl moiety is as defined hereinabove;
(K) pyridyl, optionally substituted with either one or two groups selected from the group consisting of
(1) C.sub.1 -C.sub.3 alkyl,
(2) C.sub.1 -C.sub.3 alkoxy, or
(3) halo;
(L) piperidino, optionally substituted with either one or two C.sub.1 -C.sub.3 alkyl groups;
(M) morpholino;
(N) pyrazinyl, optionally substituted with either one or two C.sub.1 -C.sub.3 alkyl groups;
(O) pyridylalkyl, containing no more than about 17 carbon atoms, in which the pyridyl moiety is as defined hereinabove;
(P) piperidinoalkyl, containing no more than about 17 carbon atoms, in which the piperidino moiety is as defined hereinabove;
(Q) morpholinoalkyl, containing no more than about 16 carbon atoms;
(R) pyrazinylalkyl, containing no more than about 16 carbon atoms, in which the pyrazinyl moiety is as defined hereinabove;
(S) tetrahydrofurylalkyl, containing no more than about 17 carbon atoms;
and
(T) substituted amino, having the formula ##STR6## in which R.sup.8 and R.sup.9 independently are selected from the group consisting of hydrogen, C.sub.1 -C.sub.18 alkyl, phenyl, and phenylalkyl, wherein the phenyl and phenylalkyl moieties are as defined hereinabove, provided that at least one of R.sup.8 and R.sup.9 is other than hydrogen;
R.sup.2 and R.sup.3 independently are selected from the group consisting of
(A) hydrogen,
(B) C.sub.1 -C.sub.3 alkyl, and
(C) phenyl, with the proviso that when one of R.sup.2 and R.sup.3 is phenyl, the other of R.sup.2 and R.sup.3 is hydrogen;
R.sup.4 represents
(A) hydrogen or
(B) C.sub.1 -C.sub.3 alkyl;
R.sup.5 represents
(A) halo,
(B) trifluoromethyl,
(C) cyano, or
(D) 1,1,2,2-tetrafluoroethoxy;
and
R.sup.6 represents
(A) hydrogen,
(B) halo, or
(C) C.sub.1 -C.sub.3 alkyl;
with the provisos that when R.sup.5 is bromo, R.sup.1 can not be 3-bromophenyl;
when R.sup.5 is cyano, R.sup.1 can not be 3-cyanophenyl;
when R.sup.5 is halo and R.sup.6 is halo, R.sup.6 can not be in the 2-position;
and when R.sup.5 is halo and R.sup.6 is C.sub.1 -C.sub.3 alkyl, R.sup.6 can not be in the 4-position.

48 more elements

Facts

Application

05/864,998Filed 27 Dec 1977

Granted

15 Sep 1981

Term ends

Not estimatedThe source records don’t support an estimate.

Classification9 codes

C07D 417/12
Containing two hetero rings: linked by a chain containing hetero atoms as chain links
A01N 47/38
Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<: containing the group >N—CO—N< where at least one nitrogen atom is part of a…
C07D 233/48
Nitrogen atoms not forming part of a nitro radical: with acyclic hydrocarbon or substituted acyclic hydrocarbon radicals, attached to said…
C07D 233/50
Nitrogen atoms not forming part of a nitro radical: with carbocyclic radicals directly attached to said nitrogen atoms