US 4,383,113 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.

Claims66

Dependent claims

A compound of the formula ##STR614## wherein when Q is O or S, then

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.sub.7 ' is H or CH.sub.3 ;
A is O or S;
A.sub.1 is O, S or SO.sub.2 ;
when
Q is O, then additional values of
R are H;
M;
CH.sub.2 CH.sub.2 OR.sub.7 ;
CH.sub.2 CH.sub.2 CH.sub.2 OR.sub.7 ;
CH(CH.sub.3)CH.sub.2 OR.sub.7 ;
CH.sub.2 OR.sub.8 ';
(CH.sub.2 CH.sub.2 O).sub.n' R.sub.8 ;
(CH(CH.sub.3)CH.sub.2 O).sub.n' R.sub.8 ;
CH.sub.2 CH.sub.2 S(O).sub.0,2 R.sub.12 ;
CH.sub.2 CH.sub.2 CH.sub.2 S(O).sub.0,2 R.sub.12 ;
R.sub.7 is CH.sub.2 CH.sub.3, CH(CH.sub.3).sub.2, phenyl, CH.sub.2 CH.sub.2 Cl or CH.sub.2 CCl.sub.3 ;
R.sub.8 ' is CH.sub.3, CH.sub.2 CH.sub.3, CH(CH.sub.3).sub.2, CH.sub.2 CH.sub.2 Cl, CH.sub.2 CCl.sub.3, phenyl, ##STR615## CH.sub.2 CH.sub.2 OCH.sub.3 or CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3 ;
R.sub.8 is CH.sub.3, CH.sub.2 CH.sub.3, CH(CH.sub.3).sub.2, phenyl, CH.sub.2 CH.sub.2 Cl or CH.sub.2 CCl.sub.3 ;
R.sub.10 and R.sub.11 are independently H, C.sub.1 -C.sub.3 alkyl, Cl, Br, OCH.sub.3 or OC.sub.2 H.sub.5 ;
R.sub.10 and R.sub.11 may be taken together to form --(CH.sub.2).sub.3 --, --(CH.sub.2).sub.4 --, --OCH.sub.2 O-- or --OCH.sub.2 CH.sub.2 O--;
n' is 2 or 3;
R.sub.12 is CH.sub.3, CH.sub.2 CH.sub.3, CH(CH.sub.3).sub.2 or phenyl;
R.sub.1 is ##STR616## 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 ;
M is an alkali metal;
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.sub.1 -C.sub.4 alkyl substituted with (a) OCH.sub.3, (b) OC.sub.2 H.sub.5, (c) CN, or (d) 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);
SCN;
N.sub.3 ;
NR.sub.16 R.sub.17 ;
OR.sub.14 or SR.sub.15 ;
R.sub.13 is H, CH.sub.3 or CH.sub.2 Cl;
n', A and A' are as previously defined;
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 of 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 ##STR617## R.sub.15 is C.sub.1 -C.sub.4 alkyl, allyl, propargyl or C.sub.1 -C.sub.2 alkyl substituted with CN;
and
Z is N;
provided that
(a) the total number of carbon atoms of R is less than or equal to 13;
(b) when Y is greater than or equal to 4 carbon atoms, R is equal to or less than 4 carbon atoms;
and
(c) 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.

75 more elements

Dependencies are inferred from the claim text.

Facts

Application: 06/268,704Filed 1 Jun 1981 · division
Priority: 30 May 1978
Granted: 10 May 1983
Term ends: Not estimatedThe source records don’t support an estimate.

Classification8 codes

C07D 239/42
One oxygen, sulfur or nitrogen atom: one nitrogen atom
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;…
C07D 239/47
Two or more oxygen, sulphur or nitrogen atoms: one nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
C07D 239/52
Two or more oxygen, sulphur or nitrogen atoms: two oxygen atoms

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
US 4,383,113 AThis patent

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

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Abstract

A compound of the formula ##STR614## wherein when Q is O or S, then

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.sub.7 ' is H or CH.sub.3 ;
A is O or S;
A.sub.1 is O, S or SO.sub.2 ;
when
Q is O, then additional values of
R are H;
M;
CH.sub.2 CH.sub.2 OR.sub.7 ;
CH.sub.2 CH.sub.2 CH.sub.2 OR.sub.7 ;
CH(CH.sub.3)CH.sub.2 OR.sub.7 ;
CH.sub.2 OR.sub.8 ';
(CH.sub.2 CH.sub.2 O).sub.n' R.sub.8 ;
(CH(CH.sub.3)CH.sub.2 O).sub.n' R.sub.8 ;
CH.sub.2 CH.sub.2 S(O).sub.0,2 R.sub.12 ;
CH.sub.2 CH.sub.2 CH.sub.2 S(O).sub.0,2 R.sub.12 ;
R.sub.7 is CH.sub.2 CH.sub.3, CH(CH.sub.3).sub.2, phenyl, CH.sub.2 CH.sub.2 Cl or CH.sub.2 CCl.sub.3 ;
R.sub.8 ' is CH.sub.3, CH.sub.2 CH.sub.3, CH(CH.sub.3).sub.2, CH.sub.2 CH.sub.2 Cl, CH.sub.2 CCl.sub.3, phenyl, ##STR615## CH.sub.2 CH.sub.2 OCH.sub.3 or CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3 ;
R.sub.8 is CH.sub.3, CH.sub.2 CH.sub.3, CH(CH.sub.3).sub.2, phenyl, CH.sub.2 CH.sub.2 Cl or CH.sub.2 CCl.sub.3 ;
R.sub.10 and R.sub.11 are independently H, C.sub.1 -C.sub.3 alkyl, Cl, Br, OCH.sub.3 or OC.sub.2 H.sub.5 ;
R.sub.10 and R.sub.11 may be taken together to form --(CH.sub.2).sub.3 --, --(CH.sub.2).sub.4 --, --OCH.sub.2 O-- or --OCH.sub.2 CH.sub.2 O--;
n' is 2 or 3;
R.sub.12 is CH.sub.3, CH.sub.2 CH.sub.3, CH(CH.sub.3).sub.2 or phenyl;
R.sub.1 is ##STR616## 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 ;
M is an alkali metal;
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.sub.1 -C.sub.4 alkyl substituted with (a) OCH.sub.3, (b) OC.sub.2 H.sub.5, (c) CN, or (d) 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);
SCN;
N.sub.3 ;
NR.sub.16 R.sub.17 ;
OR.sub.14 or SR.sub.15 ;
R.sub.13 is H, CH.sub.3 or CH.sub.2 Cl;
n', A and A' are as previously defined;
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 of 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 ##STR617## R.sub.15 is C.sub.1 -C.sub.4 alkyl, allyl, propargyl or C.sub.1 -C.sub.2 alkyl substituted with CN;
and
Z is N;
provided that
(a) the total number of carbon atoms of R is less than or equal to 13;
(b) when Y is greater than or equal to 4 carbon atoms, R is equal to or less than 4 carbon atoms;
and
(c) 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.

75 more elements

Facts

Application

06/268,704Filed 1 Jun 1981 · division

Priority

30 May 1978

Granted

10 May 1983

Term ends

Not estimatedThe source records don’t support an estimate.

Classification8 codes

C07D 239/42
One oxygen, sulfur or nitrogen atom: one nitrogen atom
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;…
C07D 239/47
Two or more oxygen, sulphur or nitrogen atoms: one nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
C07D 239/52
Two or more oxygen, sulphur or nitrogen atoms: two oxygen atoms

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

US 4,383,113 AThis patent

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