US 4,289,766 AGranted

Heterocyclic carbothioamides

AssigneeEli Lilly and Company

InventorsTerry W. Balko, Ronald E. Hackler

Life of this patent

Estimating the term…

Abstract

2-Substituted-N-(3-substituted phenyl)thiazolidine-, tetrahydro-2H-1,3-thiazine-, and benzothiazoline-3-carbothioamides, useful as insecticides.

Claims87

Dependent claims

A compound of the formula, ##STR12## 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.3 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 hereinabove;
(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 attached at a position other than the nitrogen atom, optionally substituted with either one or two C.sub.1 -C.sub.3 alkyl groups;
(M) morpholino attached at a position other than the nitrogen atom;
(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;
or
(S) tetrahydrofurylalkyl, containing no more than about 17 carbon atoms;
R.sup.2 represents hydrogen or C.sub.1 -C.sub.3 alkyl;
R.sup.3 represents
(A) halo,
(B) trifluoromethyl,
(C) cyano, or
(D) 1,1,2,2-tetrafluoroethoxy;
R.sup.4 represents
(A) hydrogen,
(B) halo, or
(C) C.sub.1 -C.sub.3 alkyl, with the provisos that when R.sup.4 is halo it can not be in the 2-position and when R.sup.4 is C.sub.1 -C.sub.3 alkyl it can not be in the 4-position;
Z represents ##STR13## ##STR14## in which each of R.sup.7 -R.sup.16, inclusive, independently is hydrogen or C.sub.1 -C.sub.3 alkyl, with the proviso that the two groups attached to any given carbon atom in (A) or (B) together can not contain more than four carbon atoms;
and
R.sup.17 represents
(1) C.sub.1 -C.sub.3 alkyl,
(2) C.sub.1 -C.sub.3 alkoxy,
(3) C.sub.1 -C.sub.3 alkylthio,
(4) trifluoromethyl,
(5) halo,
(6) cyano, or
(7) hydrogen;
with the proviso that when Z represents ##STR15## R.sup.2 is hydrogen.

47 more elements

Dependencies are inferred from the claim text.

Facts

Application: 05/865,094Filed 27 Dec 1977
Granted: 15 Sep 1981
Term ends: Not estimatedThe source records don’t support an estimate.

Classification5 codes

C07D 279/06
1,3-Thiazines; Hydrogenated 1,3-thiazines: not condensed with other rings
C07D 277/04
Not condensed with other rings: having no double bonds between ring members or between ring members and non-ring members
C07D 277/64
Benzothiazoles: with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
C07D 277/66
With only hydrocarbon or substituted hydrocarbon radicals attached in position 2: with aromatic rings or ring systems directly attached in position 2

Family

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

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Abstract

2-Substituted-N-(3-substituted phenyl)thiazolidine-, tetrahydro-2H-1,3-thiazine-, and benzothiazoline-3-carbothioamides, useful as insecticides.

A compound of the formula, ##STR12## 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.3 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 hereinabove;
(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 attached at a position other than the nitrogen atom, optionally substituted with either one or two C.sub.1 -C.sub.3 alkyl groups;
(M) morpholino attached at a position other than the nitrogen atom;
(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;
or
(S) tetrahydrofurylalkyl, containing no more than about 17 carbon atoms;
R.sup.2 represents hydrogen or C.sub.1 -C.sub.3 alkyl;
R.sup.3 represents
(A) halo,
(B) trifluoromethyl,
(C) cyano, or
(D) 1,1,2,2-tetrafluoroethoxy;
R.sup.4 represents
(A) hydrogen,
(B) halo, or
(C) C.sub.1 -C.sub.3 alkyl, with the provisos that when R.sup.4 is halo it can not be in the 2-position and when R.sup.4 is C.sub.1 -C.sub.3 alkyl it can not be in the 4-position;
Z represents ##STR13## ##STR14## in which each of R.sup.7 -R.sup.16, inclusive, independently is hydrogen or C.sub.1 -C.sub.3 alkyl, with the proviso that the two groups attached to any given carbon atom in (A) or (B) together can not contain more than four carbon atoms;
and
R.sup.17 represents
(1) C.sub.1 -C.sub.3 alkyl,
(2) C.sub.1 -C.sub.3 alkoxy,
(3) C.sub.1 -C.sub.3 alkylthio,
(4) trifluoromethyl,
(5) halo,
(6) cyano, or
(7) hydrogen;
with the proviso that when Z represents ##STR15## R.sup.2 is hydrogen.

47 more elements

Facts

Application

05/865,094Filed 27 Dec 1977

Granted

15 Sep 1981

Term ends

Not estimatedThe source records don’t support an estimate.

Classification5 codes

C07D 279/06
1,3-Thiazines; Hydrogenated 1,3-thiazines: not condensed with other rings
C07D 277/04
Not condensed with other rings: having no double bonds between ring members or between ring members and non-ring members
C07D 277/64
Benzothiazoles: with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
C07D 277/66
With only hydrocarbon or substituted hydrocarbon radicals attached in position 2: with aromatic rings or ring systems directly attached in position 2