US 4,536,576 AGranted

Agricultural sulfonamides

AssigneeE. I. Du Pont de Nemours and Company

InventorGeorge Levitt

Life of this patent

Estimating the term…

Abstract

N-(heterocyclicaminocarbonyl)arylsulfonamides in which the aryl radical is substituted in the 2-position by a carboxy radical, ester, thioester, or amide thereof; e.g. N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2-methoxycarbonylbenzenesulf onamide or N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2-methoxycarbonylbenze nesulfonamide; are useful for the regulation of plant growth and as pre-emergence and post-emergence herbicides.

Claims15

Dependent claims

A compound of the formula ##STR600## wherein Q is S;

R is C.sub.1 -C.sub.12 alkyl;
C.sub.3 -C.sub.10 alkenyl;
C.sub.3 -C.sub.10 alkynyl;
C.sub.2 -C.sub.6 alkyl substituted with 1-4 substituents selected from (a) 0-3 atoms of F, Cl or Br, (b) 0-2 OCH.sub.3 groups or (c) 0-1 cyano groups;
R is also CH.sub.2 CN;
CH(R.sub.7 ')CO.sub.2 CH.sub.3 ;
CH(R.sub.7 ')CO.sub.2 C.sub.2 H.sub.5 ;
C.sub.3 -C.sub.6 alkenyl substituted with 1-3 atoms of F, Cl or Br;
R is also C.sub.3 -C.sub.6 alkynyl substituted with one of F, Cl or Br;
R is also C.sub.5 -C.sub.8 cycloalkyl;
C.sub.5 -C.sub.8 cycloalkenyl;
C.sub.5 -C.sub.6 cycloalkyl substituted with (a) OCH.sub.3, (b) C.sub.2 -C.sub.4 alkyl, (c) F, Cl or Br or (d) 1-4 CH.sub.3 groups;
R is also C.sub.4 -C.sub.10 cycloalkylalkyl;
C.sub.4 -C.sub.8 cycloalkylalkyl substituted with 1-2 CH.sub.3 groups;
R is also C.sub.7 -C.sub.10 bicycloalkyl;
C.sub.7 -C.sub.10 bicycloalkenyl;
C.sub.10 tricycloalkyl;
C.sub.10 tricycloalkenyl;
R is also ##STR601## R.sub.7 ' is H or CH.sub.3 ;
R.sub.9 is H or C.sub.1 -C.sub.3 alkyl;
R.sub.10 and R.sub.11 are independently H, C.sub.1 -C.sub.3 alkyl, Cl, Br, OCH.sub.3, OC.sub.2 H.sub.5 or R.sub.10 and R.sub.11 may be taken together to form a 5- or 6-member ring such as ##STR602## n is 0, 1, 2 or 3 provided that the total number of carbon atoms is .ltoreq.12;
A is O or S;
A.sub.1 is O, S or SO.sub.2 ;
R.sub.1 is ##STR603## R.sub.2 is H, Cl, Br, F, C.sub.1 -C.sub.3 alkyl, NO.sub.2, SO.sub.2 CH.sub.3, OCH.sub.3, SCH.sub.3, CF.sub.3, N(CH.sub.3).sub.2, NH.sub.2 or CN;
R.sub.3 is H, Cl, Br, F or CH.sub.3 ;
R.sub.4 is H or CH.sub.3 ;
R.sub.5 is H, CH.sub.3 or OCH.sub.3 ;
W is O or S;
X is H, Cl, CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3 or OCH.sub.2 CH.sub.2 OCH.sub.3 ;
Y is H;
F;
Cl;
Br;
C.sub.1 -C.sub.4 alkyl;
C(O)L;
C.sub.1 -C.sub.4 alkyl substituted with (a) OCH.sub.3, (b) OC.sub.2 H.sub.5, (c) CN, (d) C(O)L or (e) 1-3 atoms of F, Cl or Br;
Y is also C.sub.3 -C.sub.4 alkenyl;
CH.sub.2 C.tbd.CR.sub.13 ;
A(CH.sub.2).sub.n,A.sub.1 (C.sub.1 -C.sub.3 alkyl);
ACH.sub.2 C(O)L;
ACH(CH.sub.3)C(O)L;
ACH.sub.2 CH.sub.2 C(O)L;
SCN;
N.sub.3 ;
NR.sub.16 R.sub.17 ;
OR.sub.14 or SR.sub.15 ;
L is NH.sub.2, OH, N(OCH.sub.3)CH.sub.3, NH(C.sub.1 -C.sub.4 alkyl), N(C.sub.1 -C.sub.4 alkyl).sub.2 or C.sub.1 -C.sub.6 alkoxy;
R.sub.13 is H, CH.sub.3 or CH.sub.2 Cl;
n' is 2 or 3;
A is O or S and A.sub.1 is O, S or SO.sub.2 ;
R.sub.16 is H or CH.sub.3 ;
R.sub.17 is H, OCH.sub.3, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.4 alkyl substituted with CN;
R.sub.17 is also C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.6 cycloalkyl or C.sub.2 -C.sub.3 alkyl substituted with (a) OCH.sub.3 or (b) OC.sub.2 H.sub.5 ;
R.sub.14 is C.sub.1 -C.sub.4 alkyl;
C.sub.2 -C.sub.4 alkyl substituted with 1-3 atoms or F, Cl or Br;
C.sub.1 -C.sub.4 alkyl substituted with CN;
C.sub.3 -C.sub.4 alkenyl;
CH.sub.2 C.tbd.CR.sub.13 ;
or CH.sub.2 --;
R.sub.15 is C.sub.1 -C.sub.4 alkyl, allyl, propargyl or C.sub.1 -C.sub.2 alkyl substituted with CN;
Y.sub.1 is H, OCH.sub.3 or CH.sub.3 ;
X.sub.1 is H, Cl, OCH.sub.3, OCH.sub.2 CH.sub.3 or CH.sub.3 ;
and
Z is CH;
provided that
(a) when Y is greater than or equal to 4 carbon atoms, then R is less than or equal to 4 carbon atoms;
(b) when X is Cl, then Y is Cl and when X and Y are both H, then R is less than or equal to 4 carbon atoms;
(c) X.sub.1 and Y.sub.1 are not both H;
and
(d) when R.sub.1 is ##STR604## then R.sub.4 and R.sub.5 are both H and R is .ltoreq.5 carbon atoms.

67 more elements

Dependencies are inferred from the claim text.

Facts

Application: 06/523,351Filed 15 Aug 1983 · division
Priority: 30 May 1978
Granted: 20 Aug 1985
Term ends: Not estimatedThe source records don’t support an estimate.

Classification13 codes

C07C 311/65
Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or…:…
A01N 47/28
The carbon atom having one or more single bonds to nitrogen atoms: ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
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;…
C07C 317/00
Sulfones

Family

Serial910,965Parent of this continuation-in-part · filed 30 May 1978
Serial965,070Parent of this continuation-in-part · filed 30 Nov 1978
Serial15,341Parent of this continuation-in-part · filed 1 Mar 1979
Serial29,281Parent of this continuation-in-part · filed 13 Apr 1979
Serial98,781Parent of this division · filed 30 Nov 1979
Serial452,106Parent of this division · filed 22 Dec 1982
US 4,394,506 AParent of this division
US 4,536,576 AThis patent

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

Timeline

Citations

Open elsewhere

patentgrep

Loading patent…

Abstract

A compound of the formula ##STR600## wherein Q is S;

R is C.sub.1 -C.sub.12 alkyl;
C.sub.3 -C.sub.10 alkenyl;
C.sub.3 -C.sub.10 alkynyl;
C.sub.2 -C.sub.6 alkyl substituted with 1-4 substituents selected from (a) 0-3 atoms of F, Cl or Br, (b) 0-2 OCH.sub.3 groups or (c) 0-1 cyano groups;
R is also CH.sub.2 CN;
CH(R.sub.7 ')CO.sub.2 CH.sub.3 ;
CH(R.sub.7 ')CO.sub.2 C.sub.2 H.sub.5 ;
C.sub.3 -C.sub.6 alkenyl substituted with 1-3 atoms of F, Cl or Br;
R is also C.sub.3 -C.sub.6 alkynyl substituted with one of F, Cl or Br;
R is also C.sub.5 -C.sub.8 cycloalkyl;
C.sub.5 -C.sub.8 cycloalkenyl;
C.sub.5 -C.sub.6 cycloalkyl substituted with (a) OCH.sub.3, (b) C.sub.2 -C.sub.4 alkyl, (c) F, Cl or Br or (d) 1-4 CH.sub.3 groups;
R is also C.sub.4 -C.sub.10 cycloalkylalkyl;
C.sub.4 -C.sub.8 cycloalkylalkyl substituted with 1-2 CH.sub.3 groups;
R is also C.sub.7 -C.sub.10 bicycloalkyl;
C.sub.7 -C.sub.10 bicycloalkenyl;
C.sub.10 tricycloalkyl;
C.sub.10 tricycloalkenyl;
R is also ##STR601## R.sub.7 ' is H or CH.sub.3 ;
R.sub.9 is H or C.sub.1 -C.sub.3 alkyl;
R.sub.10 and R.sub.11 are independently H, C.sub.1 -C.sub.3 alkyl, Cl, Br, OCH.sub.3, OC.sub.2 H.sub.5 or R.sub.10 and R.sub.11 may be taken together to form a 5- or 6-member ring such as ##STR602## n is 0, 1, 2 or 3 provided that the total number of carbon atoms is .ltoreq.12;
A is O or S;
A.sub.1 is O, S or SO.sub.2 ;
R.sub.1 is ##STR603## R.sub.2 is H, Cl, Br, F, C.sub.1 -C.sub.3 alkyl, NO.sub.2, SO.sub.2 CH.sub.3, OCH.sub.3, SCH.sub.3, CF.sub.3, N(CH.sub.3).sub.2, NH.sub.2 or CN;
R.sub.3 is H, Cl, Br, F or CH.sub.3 ;
R.sub.4 is H or CH.sub.3 ;
R.sub.5 is H, CH.sub.3 or OCH.sub.3 ;
W is O or S;
X is H, Cl, CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3 or OCH.sub.2 CH.sub.2 OCH.sub.3 ;
Y is H;
F;
Cl;
Br;
C.sub.1 -C.sub.4 alkyl;
C(O)L;
C.sub.1 -C.sub.4 alkyl substituted with (a) OCH.sub.3, (b) OC.sub.2 H.sub.5, (c) CN, (d) C(O)L or (e) 1-3 atoms of F, Cl or Br;
Y is also C.sub.3 -C.sub.4 alkenyl;
CH.sub.2 C.tbd.CR.sub.13 ;
A(CH.sub.2).sub.n,A.sub.1 (C.sub.1 -C.sub.3 alkyl);
ACH.sub.2 C(O)L;
ACH(CH.sub.3)C(O)L;
ACH.sub.2 CH.sub.2 C(O)L;
SCN;
N.sub.3 ;
NR.sub.16 R.sub.17 ;
OR.sub.14 or SR.sub.15 ;
L is NH.sub.2, OH, N(OCH.sub.3)CH.sub.3, NH(C.sub.1 -C.sub.4 alkyl), N(C.sub.1 -C.sub.4 alkyl).sub.2 or C.sub.1 -C.sub.6 alkoxy;
R.sub.13 is H, CH.sub.3 or CH.sub.2 Cl;
n' is 2 or 3;
A is O or S and A.sub.1 is O, S or SO.sub.2 ;
R.sub.16 is H or CH.sub.3 ;
R.sub.17 is H, OCH.sub.3, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.4 alkyl substituted with CN;
R.sub.17 is also C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.6 cycloalkyl or C.sub.2 -C.sub.3 alkyl substituted with (a) OCH.sub.3 or (b) OC.sub.2 H.sub.5 ;
R.sub.14 is C.sub.1 -C.sub.4 alkyl;
C.sub.2 -C.sub.4 alkyl substituted with 1-3 atoms or F, Cl or Br;
C.sub.1 -C.sub.4 alkyl substituted with CN;
C.sub.3 -C.sub.4 alkenyl;
CH.sub.2 C.tbd.CR.sub.13 ;
or CH.sub.2 --;
R.sub.15 is C.sub.1 -C.sub.4 alkyl, allyl, propargyl or C.sub.1 -C.sub.2 alkyl substituted with CN;
Y.sub.1 is H, OCH.sub.3 or CH.sub.3 ;
X.sub.1 is H, Cl, OCH.sub.3, OCH.sub.2 CH.sub.3 or CH.sub.3 ;
and
Z is CH;
provided that
(a) when Y is greater than or equal to 4 carbon atoms, then R is less than or equal to 4 carbon atoms;
(b) when X is Cl, then Y is Cl and when X and Y are both H, then R is less than or equal to 4 carbon atoms;
(c) X.sub.1 and Y.sub.1 are not both H;
and
(d) when R.sub.1 is ##STR604## then R.sub.4 and R.sub.5 are both H and R is .ltoreq.5 carbon atoms.

67 more elements

Facts

Application

06/523,351Filed 15 Aug 1983 · division

Priority

30 May 1978

Granted

20 Aug 1985

Term ends

Not estimatedThe source records don’t support an estimate.

Classification13 codes

C07C 311/65
Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or…:…
A01N 47/28
The carbon atom having one or more single bonds to nitrogen atoms: ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
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;…
C07C 317/00
Sulfones

Family

Serial910,965Parent of this continuation-in-part · filed 30 May 1978

Serial965,070Parent of this continuation-in-part · filed 30 Nov 1978

Serial15,341Parent of this continuation-in-part · filed 1 Mar 1979

Serial29,281Parent of this continuation-in-part · filed 13 Apr 1979

Serial98,781Parent of this division · filed 30 Nov 1979

Serial452,106Parent of this division · filed 22 Dec 1982

US 4,394,506 AParent of this division

US 4,536,576 AThis patent

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