US 4,481,029 AGranted

Triazinyl-sulfonyl-ureas and isoureas

AssigneeE. I. Du Pont de Nemours and Company

InventorGeorge Levitt

Life of this patent

Estimating the term…

Abstract

This invention relates to ureas and isoureas which are useful as herbicides and plant growth regulants. In particular, compounds of the instant invention have demonstrated great selectivity.

Claims79

Dependent claims

A compound selector from:

##STR895## wherein W' is O or S;
A' is H, Cl, Br, C.sub.1 -C.sub.4 alkyl, OCH.sub.3, NO.sub.2 or CF.sub.3 ;
##STR896##
where R.sup.III is H, C.sub.1 -C.sub.4 alkyl
or C.sub.3 -C.sub.4 alkenyl;
when Q is O or S then
R.sup.I is C.sub.1 -C.sub.6 alkyl;
C.sub.3 -C.sub.6 alkenyl;
C.sub.3 -C.sub.6 alkynyl;
C.sub.2 -C.sub.6 alkyl substituted with 1-3 Cl, F or Br, or one of CN or OCH.sub.3 ;
C.sub.3 -C.sub.6 alkenyl substituted with 1-3 Cl;
C.sub.3 -C.sub.6 alkynyl substituted with Cl;
C.sub.5 -C.sub.6 cycloalkyl;
cyclohexenyl;
cyclohexyl substituted with 1-3 CH.sub.3 ;
C.sub.4 -C.sub.7 cycloalkylalkyl or ##STR897## where R.sub.7 and R.sub.8 are independently H, Cl, CH.sub.3, or OCH.sub.3 ;
n is 0 or 1;
and
R.sup.9 is H or CH.sub.3 ;
when Q is O then
R.sup.I is ##STR898## where R.sup.16 is CH.sub.3, C.sub.2 H.sub.5, CH(CH.sub.3).sub.2, phenyl, CH.sub.2 CH.sub.2 Cl, CH.sub.2 CCl.sub.3, and n' is 2 or 3;
##STR899## where R.sub.6 ' is C.sub.1 -C.sub.4 alkyl;
provided R.sup.I has a total of .ltoreq.13 carbon atoms;
when Q is ##STR900## then R.sup.I is H;
C.sub.1 -C.sub.6 alkyl;
--CH.sub.2 CH.sub.2 OR.sub.10 ;
--CH.sub.2 CH.sub.2 CH.sub.2 OR.sub.10 ;
where R.sub.10 is CH.sub.3, CH.sub.3 CH.sub.2, CH(CH.sub.3).sub.2, or phenyl;
C.sub.3 -C.sub.6 alkenyl;
C.sub.3 -C.sub.6 cycloalkyl;
C.sub.5 -C.sub.6 cycloalkenyl;
C.sub.6 cycloalkyl substituted with any one of 1-2 OCH.sub.3, 1-3 CH.sub.3, --CH.sub.2 CH.sub.3 or CF.sub.3 ;
C.sub.4 -C.sub.7 cycloalkylalkyl;
##STR901## where R' is H, C.sub.1 -C.sub.4 alkyl, OCH.sub.3, F, Cl, Br, CN, NO.sub.2 or CF.sub.3 ;
R" is H, CH.sub.3, Cl, F or Br;
R.sub.7, R.sub.8 and R.sub.9 are as previously defined;
R.sub.6 is N, C.sub.1 -C.sub.3 alkyl;
CH.sub.2 CN;
CH.sub.2 CH.sub.2 --CN or --CH.sub.2 --CH.dbd.C.sub.2 and R.sub.6 and R.sup.I may be taken together to form --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.5 -- or --CH.sub.2 CH.sub.2 O--CH.sub.2 CH.sub.2 --;
with the proviso that when R.sub.6 is CH.sub.2 CH.sub.2 CN or CH.sub.2 CN, then R.sup.I is CH.sub.2 CH.sub.2 CN or CH.sub.2 CN;
and R.sup.I and R.sub.6 have a total carbon atom count of .ltoreq.13;
and when R.sup.I is OCH.sub.3 or OCH.sub.2 CH.sub.3 then R.sub.6 is CH.sub.3 or H;
when A is ##STR902## then R.sup.II is H, C.sub.1 -C.sub.6 alkyl;
C.sub.3 -C.sub.6 alkenyl;
phenyl;
benzyl;
benzyl or phenyl substituted with 1-2 Cl, 1-2 OCH.sub.3, 1-2 CH.sub.3 ;
C.sub.5 -C.sub.6 cycloalkyl;
C.sub.4 -C.sub.7 cycloalkylalkyl with the proviso that when T is .dbd.N--OR.sup.III, then R.sup.II must be C.sub.1 -C.sub.6 alkyl or C.sub.3 -C.sub.6 alkenyl;
B is ##STR903## where R.sub.4 is H or CH.sub.3 ;
W is O or S;
R.sub.5 is H, or CH.sub.3 ;
with the further proviso that either
R.sub.4 or R.sub.5 must be H;
R.sup.IV is C.sub.1 -C.sub.6 alkyl or C.sub.3 -C.sub.4 alkenyl;
##STR904## where Z is N;
X.dbd.H, Cl, --CH.sub.3, --OCH.sub.3 or --OCH.sub.2 CH.sub.3 ;
Y.dbd.H;
Cl;
C.sub.1 -C.sub.4 alkyl;
C.sub.1 -C.sub.4 alkyl substituted with ##STR905## or 1-3 atoms of F, Cl, Br;
C.sub.3 -C.sub.4 alkenyl;
--O--(CH.sub.2).sub.n 'O--(C.sub.1 -C.sub.3 alkyl) where n' is 2 or 3;
##STR906## --N(C.sub.1 -C.sub.4 alkyl).sub.2 or C.sub.1 -C.sub.6 alkoxy;
SCN;
--N.sub.3 ;
NR.sub.11 R.sub.12 where R.sub.11 is H or CH.sub.3 and R.sub.12 is H, --OCH.sub.3, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.2 -C.sub.3 alkyl substituted with OCH.sub.3 or OC.sub.2 H.sub.5, C.sub.1 -C.sub.2 alkyl substituted with --CN, CO.sub.2 H, CO.sub.2 CH.sub.3 or CO.sub.2 C.sub.2 H.sub.5, and R.sub.11 and R.sub.12 can be taken together to form --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 -- or CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --;
--O--R.sub.9 where R.sub.9 is C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkyl substituted with 1-3 atoms of F, Cl or Br, C.sub.1 -C.sub.2 alkyl substituted with cyano, C.sub. 3 -C.sub.4 alkenyl, --CH.sub.2 C.tbd.CR.sub.13, ##STR907## R.sub.13 is H, CH.sub.3 or CH.sub.2 Cl;
SR.sub.14 ;
where R.sub.14 is C.sub.1 -C.sub.4 alkyl, allyl, propargyl or C.sub.1 -C.sub.2 alkyl substituted with CN;
with the proviso that when X and Y are both H, then
R.sup.I and R.sup.II are less than 5 carbons;
and further provided that when A contains greater than 5 carbons atoms, then Y must contain .ltoreq.4 carbon atoms, and their agriculturally suitable salts.

70 more elements

A compound selected from ##STR927## wherein M is a cation of an alkali metal or of a tertiary amine of up to 12 carbon atoms;

W' is O or S;
A' is H, Cl, Br, C.sub.1 -14 C.sub.4 alkyl, OCH.sub.3, NO.sub.2, or CF.sub.3 ;
B is ##STR928## where R.sub.4 is H or CH.sub.3 ;
with the proviso that either R.sub.4 or R.sub.5 must be H;
R.sup.IV is C.sub.1 -C.sub.6 alkyl or C.sub.3 -C.sub.4 alkenyl;
##STR929## where Z is N;
X is H, Cl, --CH.sub.3, --OCH.sub.3 or --OCH.sub.2 CH.sub.3 ;
Y is H;
Cl;
C.sub.1 -C.sub.4 alkyl;
C.sub.1 -C.sub.4 alkyl substituted with ##STR930## or 1-3 atoms of F, Cl, Br;
Chd 3-C.sub.4 alkenyl;
--0--(CH.sub.2)n'0--(C.sub.1 -C.sub.3 alkyl) where n' is 2 or 3;
##STR931## --N(C.sub.1 -C.sub.4 alkyl).sub.2 or C.sub.1 -C.sub.6 alkoxy;
SCN;
--N.sub.3 ;
NR.sub.11 R.sub.12 where R.sub.11 is H or CH.sub.3 and R.sub.12 is H, --OCH.sub.3, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.2 -C.sub.3 alkyl substituted with OCH.sub.3 or OC.sub.2 H.sub.5, C.sub.1 -C.sub.2 alkyl substituted with --CN, CO.sub.2 H, CO.sub.2 CH.sub.3 or CO.sub.2 C.sub.2 H.sub.5, and R.sub.11 and R.sub.12 can be taken together to form --CH.sub.2 CHhd 2CH.sub.2 CH.sub.2 --or CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --;
--0l--R.sub.9 where R.sub.9 is C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkyl substituted with 1-3 atoms of F, Cl or Br, C.sub.1 -C.sub.2 alkyl substituted with cyano, C.sub.3 -C.sub.4 alkenyl, --CH.sub.2 C.tbd.CR.sub.13, ##STR932## R.sub.13 is H, CH.sub.3 or CH.sub.2 Cl;
SR.sub.14 ;
where R.sub.14 is C.sub.1 14 C.sub.4 alkyl, allyl, propargyl or C.sub.1 -C.sub.2 alkyl substituted with CN;
.

18 more elements

Dependencies are inferred from the claim text.

Facts

Application: 06/450,214Filed 16 Dec 1982 · continuation in part
Priority: 30 Nov 1979
Granted: 6 Nov 1984
Term ends: Not estimatedThe source records don’t support an estimate.

Classification7 codes

C07D 521/00
Heterocyclic compounds containing unspecified hetero rings
A01N 47/36
Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<: containing the group >N—CO—N< directly attached to at least one heterocyclic ring;…
A01N 47/42
The carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides: containing —N=CX2 groups, e.g. isothiourea
C07D 307/68
With hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals,…:…

Family

Serial98,723Parent of this continuation-in-part · filed 30 Nov 1979
Serial196,276Parent of this continuation-in-part · filed 22 Oct 1980
US 4,481,029 AThis patent

From the US filing history. Foreign family members aren’t listed.

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Abstract

This invention relates to ureas and isoureas which are useful as herbicides and plant growth regulants. In particular, compounds of the instant invention have demonstrated great selectivity.

A compound selector from:

##STR895## wherein W' is O or S;
A' is H, Cl, Br, C.sub.1 -C.sub.4 alkyl, OCH.sub.3, NO.sub.2 or CF.sub.3 ;
##STR896##
where R.sup.III is H, C.sub.1 -C.sub.4 alkyl
or C.sub.3 -C.sub.4 alkenyl;
when Q is O or S then
R.sup.I is C.sub.1 -C.sub.6 alkyl;
C.sub.3 -C.sub.6 alkenyl;
C.sub.3 -C.sub.6 alkynyl;
C.sub.2 -C.sub.6 alkyl substituted with 1-3 Cl, F or Br, or one of CN or OCH.sub.3 ;
C.sub.3 -C.sub.6 alkenyl substituted with 1-3 Cl;
C.sub.3 -C.sub.6 alkynyl substituted with Cl;
C.sub.5 -C.sub.6 cycloalkyl;
cyclohexenyl;
cyclohexyl substituted with 1-3 CH.sub.3 ;
C.sub.4 -C.sub.7 cycloalkylalkyl or ##STR897## where R.sub.7 and R.sub.8 are independently H, Cl, CH.sub.3, or OCH.sub.3 ;
n is 0 or 1;
and
R.sup.9 is H or CH.sub.3 ;
when Q is O then
R.sup.I is ##STR898## where R.sup.16 is CH.sub.3, C.sub.2 H.sub.5, CH(CH.sub.3).sub.2, phenyl, CH.sub.2 CH.sub.2 Cl, CH.sub.2 CCl.sub.3, and n' is 2 or 3;
##STR899## where R.sub.6 ' is C.sub.1 -C.sub.4 alkyl;
provided R.sup.I has a total of .ltoreq.13 carbon atoms;
when Q is ##STR900## then R.sup.I is H;
C.sub.1 -C.sub.6 alkyl;
--CH.sub.2 CH.sub.2 OR.sub.10 ;
--CH.sub.2 CH.sub.2 CH.sub.2 OR.sub.10 ;
where R.sub.10 is CH.sub.3, CH.sub.3 CH.sub.2, CH(CH.sub.3).sub.2, or phenyl;
C.sub.3 -C.sub.6 alkenyl;
C.sub.3 -C.sub.6 cycloalkyl;
C.sub.5 -C.sub.6 cycloalkenyl;
C.sub.6 cycloalkyl substituted with any one of 1-2 OCH.sub.3, 1-3 CH.sub.3, --CH.sub.2 CH.sub.3 or CF.sub.3 ;
C.sub.4 -C.sub.7 cycloalkylalkyl;
##STR901## where R' is H, C.sub.1 -C.sub.4 alkyl, OCH.sub.3, F, Cl, Br, CN, NO.sub.2 or CF.sub.3 ;
R" is H, CH.sub.3, Cl, F or Br;
R.sub.7, R.sub.8 and R.sub.9 are as previously defined;
R.sub.6 is N, C.sub.1 -C.sub.3 alkyl;
CH.sub.2 CN;
CH.sub.2 CH.sub.2 --CN or --CH.sub.2 --CH.dbd.C.sub.2 and R.sub.6 and R.sup.I may be taken together to form --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.5 -- or --CH.sub.2 CH.sub.2 O--CH.sub.2 CH.sub.2 --;
with the proviso that when R.sub.6 is CH.sub.2 CH.sub.2 CN or CH.sub.2 CN, then R.sup.I is CH.sub.2 CH.sub.2 CN or CH.sub.2 CN;
and R.sup.I and R.sub.6 have a total carbon atom count of .ltoreq.13;
and when R.sup.I is OCH.sub.3 or OCH.sub.2 CH.sub.3 then R.sub.6 is CH.sub.3 or H;
when A is ##STR902## then R.sup.II is H, C.sub.1 -C.sub.6 alkyl;
C.sub.3 -C.sub.6 alkenyl;
phenyl;
benzyl;
benzyl or phenyl substituted with 1-2 Cl, 1-2 OCH.sub.3, 1-2 CH.sub.3 ;
C.sub.5 -C.sub.6 cycloalkyl;
C.sub.4 -C.sub.7 cycloalkylalkyl with the proviso that when T is .dbd.N--OR.sup.III, then R.sup.II must be C.sub.1 -C.sub.6 alkyl or C.sub.3 -C.sub.6 alkenyl;
B is ##STR903## where R.sub.4 is H or CH.sub.3 ;
W is O or S;
R.sub.5 is H, or CH.sub.3 ;
with the further proviso that either
R.sub.4 or R.sub.5 must be H;
R.sup.IV is C.sub.1 -C.sub.6 alkyl or C.sub.3 -C.sub.4 alkenyl;
##STR904## where Z is N;
X.dbd.H, Cl, --CH.sub.3, --OCH.sub.3 or --OCH.sub.2 CH.sub.3 ;
Y.dbd.H;
Cl;
C.sub.1 -C.sub.4 alkyl;
C.sub.1 -C.sub.4 alkyl substituted with ##STR905## or 1-3 atoms of F, Cl, Br;
C.sub.3 -C.sub.4 alkenyl;
--O--(CH.sub.2).sub.n 'O--(C.sub.1 -C.sub.3 alkyl) where n' is 2 or 3;
##STR906## --N(C.sub.1 -C.sub.4 alkyl).sub.2 or C.sub.1 -C.sub.6 alkoxy;
SCN;
--N.sub.3 ;
NR.sub.11 R.sub.12 where R.sub.11 is H or CH.sub.3 and R.sub.12 is H, --OCH.sub.3, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.2 -C.sub.3 alkyl substituted with OCH.sub.3 or OC.sub.2 H.sub.5, C.sub.1 -C.sub.2 alkyl substituted with --CN, CO.sub.2 H, CO.sub.2 CH.sub.3 or CO.sub.2 C.sub.2 H.sub.5, and R.sub.11 and R.sub.12 can be taken together to form --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 -- or CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --;
--O--R.sub.9 where R.sub.9 is C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkyl substituted with 1-3 atoms of F, Cl or Br, C.sub.1 -C.sub.2 alkyl substituted with cyano, C.sub. 3 -C.sub.4 alkenyl, --CH.sub.2 C.tbd.CR.sub.13, ##STR907## R.sub.13 is H, CH.sub.3 or CH.sub.2 Cl;
SR.sub.14 ;
where R.sub.14 is C.sub.1 -C.sub.4 alkyl, allyl, propargyl or C.sub.1 -C.sub.2 alkyl substituted with CN;
with the proviso that when X and Y are both H, then
R.sup.I and R.sup.II are less than 5 carbons;
and further provided that when A contains greater than 5 carbons atoms, then Y must contain .ltoreq.4 carbon atoms, and their agriculturally suitable salts.

70 more elements

Facts

Application

06/450,214Filed 16 Dec 1982 · continuation in part

Priority

30 Nov 1979

Granted

6 Nov 1984

Term ends

Not estimatedThe source records don’t support an estimate.

Classification7 codes

C07D 521/00
Heterocyclic compounds containing unspecified hetero rings
A01N 47/36
Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<: containing the group >N—CO—N< directly attached to at least one heterocyclic ring;…
A01N 47/42
The carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides: containing —N=CX2 groups, e.g. isothiourea
C07D 307/68
With hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals,…:…