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US 4,302,451 AGranted
Pesticidal phosphorus sulfenamides
AssigneeE. I. Du Pont de Nemours and Company
InventorCaleb W. Holyoke, Jr.
Life of this patent
Estimating the term…
Abstract
[(N,N-diarylamino)thio]phosphoramide compounds such as N-[N-[2-chloro-5-(trifluoromethyl)phenyl]-N-[2,4-dinitro-6-(trifluoromethy l)phenyl]amino thio]-N-(1-methylethyl)phosphoramidic acid, diethyl ester, are useful as miticides, insecticides, fungicides and ovicides.
Claims48
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, OCHF.sub.2, OCF.sub.3, OCF.sub.2 CF.sub.2 H or S(O).sub.k R.sub.9 ;
- or R.sub.3 and R.sub.4 may be taken together to form --OCF.sub.2 O-- or --OCF.sub.2 OCF.sub.2 --;
- 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 ;
- R.sub.6 is H, NO.sub.2 or CF.sub.3 ;
- R.sub.7 is NO.sub.2 or CF.sub.3 ;
- k is 0, 1 or 2;
- R.sub.9 is C.sub.1 -C.sub.2 alkyl optionally substituted with 2-4 Cl and/or F;
- ##STR33## where R.sub.8 is C.sub.1 -C.sub.8 alkyl optionally substituted with F, Br, Cl or I, CN, OCH.sub.3, OCH.sub.2 CH.sub.3 ;
- phenyl or benzyl, each can be optionally substituted with Cl, F, Br, I, CH.sub.3, OCH.sub.3, NO.sub.2 or CF.sub.3 ;
- ##STR34## where R.sub.9a is C.sub.1 -C.sub.4 alkyl or phenyl optionally substituted with F, Cl, Br, I, NO.sub.2, CH.sub.3, OCH.sub.3 or CF.sub.3 ;
- X is O or S;
- Y.sub.1 or Y.sub.2 are independently:
- C.sub.1 -C.sub.4 alkyl optionally substituted with one or more F, Cl, Br or I, OCH.sub.3, OCH.sub.2 CH.sub.3, CN, CH.sub.3 S, CH.sub.3 CH.sub.2 S;
- C.sub.2 -C.sub.4 alkenyl optionally substituted with one or more F, Cl, carboxy or carboalkoxy;
- benzyl which can be optionally substituted with F, Cl, Br, I, NO.sub.2, CH.sub.3, OCH.sub.3 or CF.sub.3 ;
- C.sub.1 -C.sub.4 alkoxy optionally substituted with one to three atoms of F, Cl, Br, CH.sub.3 O, CH.sub.3 CH.sub.2 O or combinations thereof;
- C.sub.1 -C.sub.4 thioalkyl optionally substituted with one to three of the groups F, Cl, Br, I, carboxy or carboalkoxy, or combinations thereof;
- phenyl, phenoxy or thiophenoxy each optionally substituted with one to three of the groups F, Cl, Br, I, NO.sub.2, CH.sub.3, CF.sub.3 or combinations thereof;
- or NR.sub.10 R.sub.11 where
- R.sub.10 is C.sub.1 -C.sub.4 alkyl or OCH.sub.3 ;
- R.sub.11 is C.sub.1 -C.sub.4 alkyl;
- and
- R.sub.10 and R.sub.11 can be taken together to form ##STR35## Y.sub.1 and Y.sub.2 can be taken together to form ##STR36## and R.sub.12 is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 Alkoxy or Halogen
- where
- Z.sub.1, Z.sub.2, Z.sub.3, Z.sub.4, Z.sub.5 or Z.sub.6 are independently H, CH.sub.3 or CH.sub.3 CH.sub.2 ;
- n is 3 or 4;
- l is 0 or 1;
- 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) R.sub.6 and R.sub.7 are not simultaneously CF.sub.3 ;
- and
- (5) further provided that when R.sub.6 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.
- (6) when R.sub.10 is OCH.sub.3, R.sub.11 is C.sub.1 -C.sub.4 alkyl;
- (7) only one of Y.sub.1 and Y.sub.2 is NR.sub.10 R.sub.11 ;
- (8) only one of R.sub.10 and R.sub.11 is phenyl or substituted phenyl.
38 more elements
Dependencies are inferred from the claim text.