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US 4,309,425 AGranted
Miticidal, insecticidal, ovicidal and fungicidal N-(N',N'-diarylaminothio)sulfonamides
AssigneeE. I. Du Pont de Nemours and Company
InventorJiin-Duey Cheng
Life of this patent
Estimating the term…
Abstract
Sulfonamides, such as N-[N-(2-chloro-5-(trifluoromethyl)phenyl]-N-[2,4-dinitro-6-(trifluoromethy l)phenyl]aminothio]-N,4-dimethylbenzenesulfonamide, are useful for control of arthropod pests of plants and animals and fungus disease of plants.
Claims31
A compound of the formula:
- ##STR23## wherein R.sub.1, R.sub.3 and R.sub.4 are independently H, F, Cl, Br, NO.sub.2, CF.sub.3, OCF.sub.3, OCF.sub.2 CF.sub.2 H or S(O).sub.k R.sub.9 ;
- R.sub.2 is H, F, Cl, Br, NO.sub.2, CF.sub.3 or S(O).sub.k R.sub.9 ;
- R.sub.5 is H, Cl, F, Br or NO.sub.2 ;
- Z is --NR.sub.6 SO.sub.2 R.sub.13, ##STR24## R.sub.6 is C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.4 chloroalkyl, ##STR25## or R.sub.14 CHCOR.sub.15 ;
- R.sub.7 is H, C.sub.1 -C.sub.12 alkyl, C.sub.1 -C.sub.4 alkoxy, Cl, Br or F;
- R.sub.8 is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, Cl, Br, F, CF.sub.3, NO.sub.2, R.sub.11 S(O).sub.k or CO.sub.2 R.sub.12 ;
- R.sub.9 is C.sub.1 -C.sub.2 alkyl or C.sub.1 -C.sub.2 alkyl substituted with 2 to 4 atoms or Cl and/or F;
- R.sub.10 is H, NO.sub.2 or CF.sub.3 ;
- R.sub.11 is C.sub.1 -C.sub.2 alkyl or C.sub.2 -C.sub.4 dialkylamino,
- R.sub.12 is C.sub.1 -C.sub.4 alkyl;
- R.sub.13 is ##STR26## naphthyl, NR.sub.16 R.sub.17, CF.sub.3 or C.sub.1 -C.sub.20 alkyl;
- R.sub.14 is H or CH.sub.3 ;
- R.sub.15 is C.sub.1 -C.sub.4 alkoxy or N(R.sub.17).sub.2 ;
- R.sub.16 is C.sub.1 -C.sub.3 alkyl, OCH.sub.3 or ##STR27## R.sub.17 is C.sub.1 -C.sub.3 alkyl;
- R.sub.18 is H, C.sub.1 -C.sub.8 alkyl, ##STR28## or NR.sub.16 R.sub.17 ;
- A is --(CH.sub.2).sub.3 --, --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.5 --, X(CH.sub.2).sub.2 -- or --X(CH.sub.2).sub.3 --, where X is O, S, or NR.sub.19 and where X is bonded to the carbonyl carbon of Z;
- R.sub.19 is C.sub.1 -C.sub.4 alkyl, or phenyl optionally substituted with 1 or 2 groups selected from F, Cl, Br, CH.sub.3 or OCH.sub.3 ;
- R.sub.20 is NO.sub.2 or CF.sub.3 ;
- k is 0, 1 or 2;
- and
- m is 1 or 2;
- provided that
- (1) at least two of R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are hydrogen;
- (2) no more than two of the substituents R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are simultaneously NO.sub.2 or CF.sub.3 ;
- (3) when two NO.sub.2 or two S(O).sub.k R.sub.9 groups are present, they are not ortho to one another;
- (4) only one of R.sub.6 and R.sub.13 or one of R.sub.6 and R.sub.16 or one of R.sub.6 and R.sub.18 is ##STR29## (5) when R.sub.11 is dialkylamino, then k is 2;
- and (6) R.sub.10 and R.sub.20 are not simultaneously CF.sub.3 ;
- and further provided that when R.sub.10 is NO.sub.2, then
- (a) R.sub.1 is H, F or Cl when R.sub.3 is other than H, F or Cl;
- (b) when R.sub.1 =R.sub.3 =R.sub.5, then R.sub.1, R.sub.3 and R.sub.5 are either H or F;
- and
- (c) R.sub.5 is either H or F.
29 more elements
A process for preparing a compound of the formula:
- ##STR32## wherein R.sub.1, R.sub.3 and R.sub.4 are independently H, F, Cl, Br, NO.sub.2, CF.sub.3, OCF.sub.3, OCF.sub.2 CF.sub.2 H or S(O).sub.k R.sub.9 ;
- R.sub.2 is H, F, Cl, Br, NO.sub.2, CF.sub.3 or S(O).sub.k R.sub.9 ;
- R.sub.5 is H, Cl, F, Br, or NO.sub.2 ;
- Z is --NR.sub.6 SO.sub.2 R.sub.13, ##STR33## R.sub.6 is C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.4 chloroalkyl, ##STR34## or R.sub.14 CHCOR.sub.15 ;
- R.sub.7 is H, C.sub.1 -C.sub.12 alkyl, C.sub.1 -C.sub.4 alkoxy, Cl, Br or F;
- R.sub.8 is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, Cl, Br, F, CF.sub.3, NO.sub.2, R.sub.11 S(O).sub.k or CO.sub.2 R.sub.12 ;
- R.sub.9 is C.sub.1 -C.sub.2 alkyl or C.sub.1 -C.sub.2 alkyl substituted with 2 to 4 atoms or Cl and/or F;
- R.sub.10 is H, NO.sub.2 or CF.sub.3 ;
- R.sub.11 is C.sub.1 -C.sub.2 alkyl or C.sub.2 -C.sub.4 dialkylamino,
- R.sub.12 is C.sub.1 -C.sub.4 alkyl;
- R.sub.13 is ##STR35## naphthyl, NR.sub.16 R.sub.17, CF.sub.3 or C.sub.1 -C.sub.20 alkyl;
- R.sub.14 is H or CH.sub.3 ;
- R.sub.15 is C.sub.1 -C.sub.4 alkoxy or N(R.sub.17).sub.2 ;
- R.sub.16 is C.sub.1 -C.sub.3 alkyl, OCH.sub.3 or ##STR36## R.sub.17 is C.sub.1 -C.sub.3 alkyl;
- R.sub.18 is H, C.sub.1 -C.sub.8 alkyl, ##STR37## or NR.sub.16 R.sub.17 ;
- A is --(CH.sub.2).sub.3 --, --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.5 --, X(CH.sub.2).sub.2 -- or --X(CH.sub.2).sub.3 --, where X is O, S or NR.sub.19 and where X is bonded to the carbonyl carbon of Z;
- R.sub.19 is C.sub.1 -C.sub.4 alkyl, or phenyl optionally substituted with 1 or 2 groups selected from F, Cl, Br, CH.sub.3 or OCH.sub.3 ;
- R.sub.20 is NO.sub.2 or CF.sub.3 ;
- k is 0, 1 or 2;
- and
- m is 1 or 2;
- provided that
- (1) at least two of R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are hydrogen;
- (2) no more than two of the substituents R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are simultaneously NO.sub.2 or CF.sub.3 ;
- (3) when two NO.sub.2 or two S(O).sub.k R.sub.9 groups are present, they are not ortho to one another;
- (4) only one of R.sub.6 and R.sub.13 or one of R.sub.6 and R.sub.16 or one of R.sub.6 and R.sub.18 is ##STR38## (5) when R.sub.11 is dialkylamino, then k is 2;
- and (6) R.sub.10 and R.sub.20 are not simultaneously CF.sub.3 ;
- and further provided that when R.sub.10 is NO.sub.2, then
- (a) R.sub.1 is H, F or Cl when R.sub.3 is other than H, F or Cl;
- (b) when R.sub.1 =R.sub.3 =R.sub.5, then R.sub.1, R.sub.3 and R.sub.5 are either H or F;
- and
- (c) R.sub.5 is either H or F;
- consisting essentially of
- (a.) contacting a compound of the formula ##STR39## where R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.10 and R.sub.20 are as defined above, with an equivalent amount of a metal hydride or alkali hydroxide;
- and
- (b.) contacting the product of (a) with an equivalent or excess of a sulfenyl chloride of the formula ClSZ, where Z is as defined above.
33 more elements
Dependencies are inferred from the claim text.