Patent US3215190A successfully refreshed from Google Patents.
Patent US4838925A successfully refreshed from Google Patents.
US4838925A
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Heterocyclic acyl sulfonamides
Assignee: EIDP Inc
•
Filing: 1987-09-25
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Granted: 1989-06-13
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Expires: 2007-09-25
Abstract
Abstract This invention relates to novel heterocyclic carbonyl sulfonamides which are particularly useful as agricultural chemicals.
Inventors
- 👤 Chi-Ping Tseng
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 04:12
CPC Classifications
C; C07; C07D; C07D487/00; C07D487/02; C07D487/04; A; A01; A01N; A01N43/00; A01N43/90
Claims Analysis
Total Claims: 45
Claim 1
Independent Claim
1731 words
A compound selected from ##STR60## wherein R is H; C 1 -C 3 alkyl optionally substituted with halogen; C 1 -C 3 thioalkyl optionally substituted with halogen; benzyl optionally substituted with F, Cl, OCH 3 , SCH 3 or NO 2 ; allyl; propargyl; --C(O)(C 1 -C 3 alkyl); CO 2 CH 3 ; or CO 2 CH 2 CH 3 ; G is Cl, OR' or SR'; R' is C 1 -C 3 alkyl optionally substituted with halogen; W is O, S, NR" or NOR"; R" is H or C 1 -C 3 alkyl optionally substituted with halogen; L is ##STR61## R 1 is H; halogen; NO 2 ; CH; C 1 -C 4 alkyl optionally substituted with F, Cl, Br, CN, OCH 3 or SCH 3 ; C 2 -C 4 alkenyl optionally substituted with F, Cl, Br, OCH 3 or SMe; C 3 -C 4 alkynyl; C 3 -C 5 cycloalkyl optionally substituted with F, Cl or CH 3 ; C(O)R 16 ; C(OCH 2 CH 2 O)R 16 ; C(R 16 )(OR 17 )(OR 18 ); CO 2 R 19 ; C(O)NR 20 R 21 ; N 3 ; S(O) 2 NR 22 R 23 ; S(O) 2 OR 24 ; OS(O) 2 R 25 ; phenyl optionally substituted by F, Cl, Br, CH 3 or OCH 3 ; ER 26 ; (CH 2 ) n Q or (CH 2 ) n Q 1 ; R 2 is H, halogen, CN, NO 2 , C 1 -C 3 alkyl optionally substituted with halogen, CO 2 R 19 , S(O) 2 NR 27 R 28 ; NR 29 R 30 ; ER 31 ; or C 1 -C 2 alkyl substituted with C 1 -C 2 alkoxy, C 1 -C 2 haloalkoxy, C 1 -C 2 alkylthio, C 1 -C 2 haloalkylthio, CN, OH or SH; R 2 ' is independently H, F, Cl, Br, CH 3 , OCH 3 , or SCH 3 ; R 3 is H, CH 3 , OCH 3 , OCF 2 H, F, Cl, Br, CO 2 R 19 , S(O) 2 N(CH 3 ) 2 , OS(O) 2 CH 3 or S(O) p CH 3 ; R 4 is Cl, NO 2 , CO 2 CH 3 , CO 2 CH 2 CH 3 , C(O)N(CH 3 ) 2 , OS(O) 2 CH 3 , S(O) 2 CH 3 , S(O) 2 CH 2 CH 3 , OCH 3 or OCH 2 CH 3 ; R 5 is H, C 1 -C 3 alkyl, F, Cl, Br, NO 2 , S(O) 2 NR 32 R 33 , S(O) 2 N(OCH 3 )CH 3 or S(O) p R 34 ; R 6 is C 1 -C 3 alkyl or phenyl; R 7 is H, C 1 -C 3 alkyl optionally substituted with halogen, C 3 -C 4 alkenyl, or phenyl; R 8 is H or CH 3 ; R 9 is H, CH 3 or CH 2 CH 3 ; R 10 is H, CH 3 or CH 2 CH 3 ; R 11 is H, Cl or C 1 -C 3 alkyl; R 12 is H, C 1 -C 4 alkyl optionally substituted with F, Cl, Br or OCH 3 ; C 3 -C 5 cycloalkyl optionally substituted with F, Cl or OCH 3 ; C 3 -C 4 alkenyl; or C 3 -C 4 alkynyl; R 13 is H or C 1 -C 3 alkyl; R 14 is H, F, Cl, Br, CH 3 or CH 2 CH 3 ; R 15 is H, F, Cl, Br, CH 3 or CH 2 CH 3 ; R 16 is C 1 -C 4 alkyl optionally substituted with F, Cl, Br or OCH 3 ; C 3 -C 5 cycloalkyl optionally substituted with F or Cl; or C 3 -C 4 alkenyl; R 17 and R 18 are independently C 1 -C 3 alkyl; R 19 is C 1 -C 4 alkyl, C 3 -C 4 alkenyl, C 3 -C 4 alkynyl; C 2 -C 4 haloalkyl, C 2 -C 3 cyanoalkyl, C 3 -C 6 cycloalkyl, C 4 -C 7 cycloalkylalkyl or C 2 -C 4 alkoxyalkyl; R 20 is H, CH 3 or CH 2 CH 3 ; R 21 is CH 3 , CH 2 CH 3 , CH 2 CH 2 CH 3 , OCH 3 or OCH 2 CH 3 ; or R 20 and R 21 may be taken together to form --(CH 2 ) 2 (CH 2 ) n (CH 2 ) 2 -- and --CH 2 CH 2 OCH 2 CH 2 --; R 22 is C 1 -C 4 alkyl, C 2 -C 3 cyanoalkyl, OCH 3 , OCH 2 CH 3 , N(CH 3 ) 2 , C 3 -C 4 alkenyl, C 3 -C 4 alkynyl, cyclopropylmethyl or C 3 -C 4 cycloalkyl; R 23 is H, C 1 -C 4 alkyl or C 3 -C 4 alkenyl; or R 22 and R 23 may be taken together as --(CH 2 ) 3 --, --(CH 2 ) 4 -- or --CH 2 CH 2 OCH 2 CH 2 --; R 24 is C 1 -C 3 alkyl or C 1 -C 3 haloalkyl; R 25 is C 1 -C 3 alkyl or N(CH 3 ) 2 ; R 26 is C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 4 alkoxyalkyl, C 3 -C 4 alkenyl, C 3 -C 4 alkynyl, phenyl optionally substituted by F, Cl, Br, CH 3 or OCH 3 , or C 2 -C 4 haloalkenyl; R 27 is C 1 -C 3 alkyl; R 28 is H, C 1 -C 4 alkyl or methoxy; R 27 and R 28 may be taken together to form --(CH 2 ) 4 --, --(CH 2 ) 5 -- or --CH 2 CH 2 OCH 2 CH 2 --; R 29 and R 30 are independently H, CH 3 or CH 2 CH 3 ; R 31 is C 1 -C 4 alkyl optionally substituted with F, Cl or OCH 3 ; R 32 is CH 3 or CH 2 CH 3 ; R 33 is H, CH 3 or CH 2 CH 3 ; R 34 is C 1 -C 3 alkyl, C 3 -C 4 alkenyl or C 3 -C 4 alkynyl; Q a is O, S, S(O), S(O) 2 or NCH 3 ; Q b is O, S, or S(O) 2 ; Q c is O, S, NH, N(C 1 -C 3 alkyl), NCH 2 CH═CH 2 or NCH 2 C.tbd.CH; Q d is O, NH, N(C 1 -C 3 alkyl), NCH 2 CH═CH 2 or NCH 2 C.tbd.CH; Q e is O or NR 12 ; Q f is C(O) or S(O) 2 ; Q g is O, S, NH or N(C 1 -C 3 alkyl); n is 0 or 1; p is 0, 1 or 2; W' is O or S; E is O, S, S(O) or S(O) 2 ; Q is ##STR62## Q 1 is ##STR63## wherein Q 1 -1 through Q 1 -87 may be optionally substituted with 1 or 2 groups selected from C 1 -C 2 alkyl or C 1 -C 2 haloalkyl; R 35 is H, C 1 -C 3 alkyl or allyl; R 36 and R 37 are independently H or C 1 -C 3 alkyl; X b is O or NR 36 ; and X c is O, S, S(O), S(O) 2 or NR 36 ; A is ##STR64## X or Y is H, halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 haloalkylthio, C 1 -C 4 alkylthio, C 2 -C 5 alkoxyalkyl, C 2 -C 5 alkoxyalkoxy, amino, C 1 -C 3 alkylamino, di(C 1 -C 3 alkyl)amino, C 3 -C 4 alkenyloxy, C 3 -C 4 alkynyloxy, C 2 -C 5 alkylsulfinylalkyl, C 1 -C 4 haloalkyl, C 2 -C 5 alkylsulfonylalkyl, C 3 -C 5 cycloalkyl, C 2 -C 4 alkynyl, C 2 -C 5 alkylthioalkyl, ##STR65## or N(OCH 3 )CH 3 ; W 1 and W 2 are independently O or S; m and m' are independently 2 or 3; R a is H or CH 3 ; R b and R c are independently C 1 -C 2 alkyl; Z is CH, N, CCH 3 , CCH 2 CH 3 , CCl or CBr; Z 1 is C--U, N or N--O; Z 2 and Z 3 are independently N or C--U; Z 4 is NCH 3 , O, S or CH 2 ; U is H, F, Cl, Br, C 1 -C 2 alkyl optionally substituted by F, Cl, Br or OCH 3 , CN, NO 2 , NMe 2 , OR'", SR'" or CO 2 CH 3 ; R'" is C 1 -C 2 alkyl optionally substituted with F, Cl, Br or OCH 3 ; X a is CH 3 , CH 2 CH 3 or CH 2 CF 3 ; and X d is H or CH 3 ; and their agriculturally suitable salts; provided that (1) the total number of carbon atoms of R 22 and R 23 is less than or equal to five; (2) when X or Y is Cl, F, Br or I, then Z is CH and the remaining X or Y is OCH 3 , OCH 2 CH 3 , N(OCH 3 )CH 3 , NHCH 3 , N(CH 3 ) 2 or OCF 2 H; (3) when X or Y is C 1 haloalkoxy, then Z is CH; (4) at least one of X or Y is X' where X' is H, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkylthio, C 1 -C 4 alkylthio, C 2 -C 5 alkoxyalkoxy, amino, C 1 -C 3 alkylamino or di(C 1 -C 3 alkyl)amino; (5) the total number of carbon atoms of R 27 and R 28 is less than or equal to five; (6) when A is A-1, A-2, A-7 or A-19 then Z is a carbon value, and when A is A-3, A-4, A-5, A-6, A-8 and A-9 then Z is N; and (7) when A is A-11 then one of Z 1 , Z 2 or Z 3 is N.
Claim 2
Dependent Claim
1731 words
A compound selected from ##STR60## wherein R is H; C 1 -C 3 alkyl optionally substituted with halogen; C 1 -C 3 thioalkyl optionally substituted with halogen; benzyl optionally substituted with F, Cl, OCH 3 , SCH 3 or NO 2 ; allyl; propargyl; --C(O)(C 1 -C 3 alkyl); CO 2 CH 3 ; or CO 2 CH 2 CH 3 ; G is Cl, OR' or SR'; R' is C 1 -C 3 alkyl optionally substituted with halogen; W is O, S, NR" or NOR"; R" is H or C 1 -C 3 alkyl optionally substituted with halogen; L is ##STR61## R 1 is H; halogen; NO 2 ; CH; C 1 -C 4 alkyl optionally substituted with F, Cl, Br, CN, OCH 3 or SCH 3 ; C 2 -C 4 alkenyl optionally substituted with F, Cl, Br, OCH 3 or SMe; C 3 -C 4 alkynyl; C 3 -C 5 cycloalkyl optionally substituted with F, Cl or CH 3 ; C(O)R 16 ; C(OCH 2 CH 2 O)R 16 ; C(R 16 )(OR 17 )(OR 18 ); CO 2 R 19 ; C(O)NR 20 R 21 ; N 3 ; S(O) 2 NR 22 R 23 ; S(O) 2 OR 24 ; OS(O) 2 R 25 ; phenyl optionally substituted by F, Cl, Br, CH 3 or OCH 3 ; ER 26 ; (CH 2 ) n Q or (CH 2 ) n Q 1 ; R 2 is H, halogen, CN, NO 2 , C 1 -C 3 alkyl optionally substituted with halogen, CO 2 R 19 , S(O) 2 NR 27 R 28 ; NR 29 R 30 ; ER 31 ; or C 1 -C 2 alkyl substituted with C 1 -C 2 alkoxy, C 1 -C 2 haloalkoxy, C 1 -C 2 alkylthio, C 1 -C 2 haloalkylthio, CN, OH or SH; R 2 ' is independently H, F, Cl, Br, CH 3 , OCH 3 , or SCH 3 ; R 3 is H, CH 3 , OCH 3 , OCF 2 H, F, Cl, Br, CO 2 R 19 , S(O) 2 N(CH 3 ) 2 , OS(O) 2 CH 3 or S(O) p CH 3 ; R 4 is Cl, NO 2 , CO 2 CH 3 , CO 2 CH 2 CH 3 , C(O)N(CH 3 ) 2 , OS(O) 2 CH 3 , S(O) 2 CH 3 , S(O) 2 CH 2 CH 3 , OCH 3 or OCH 2 CH 3 ; R 5 is H, C 1 -C 3 alkyl, F, Cl, Br, NO 2 , S(O) 2 NR 32 R 33 , S(O) 2 N(OCH 3 )CH 3 or S(O) p R 34 ; R 6 is C 1 -C 3 alkyl or phenyl; R 7 is H, C 1 -C 3 alkyl optionally substituted with halogen, C 3 -C 4 alkenyl, or phenyl; R 8 is H or CH 3 ; R 9 is H, CH 3 or CH 2 CH 3 ; R 10 is H, CH 3 or CH 2 CH 3 ; R 11 is H, Cl or C 1 -C 3 alkyl; R 12 is H, C 1 -C 4 alkyl optionally substituted with F, Cl, Br or OCH 3 ; C 3 -C 5 cycloalkyl optionally substituted with F, Cl or OCH 3 ; C 3 -C 4 alkenyl; or C 3 -C 4 alkynyl; R 13 is H or C 1 -C 3 alkyl; R 14 is H, F, Cl, Br, CH 3 or CH 2 CH 3 ; R 15 is H, F, Cl, Br, CH 3 or CH 2 CH 3 ; R 16 is C 1 -C 4 alkyl optionally substituted with F, Cl, Br or OCH 3 ; C 3 -C 5 cycloalkyl optionally substituted with F or Cl; or C 3 -C 4 alkenyl; R 17 and R 18 are independently C 1 -C 3 alkyl; R 19 is C 1 -C 4 alkyl, C 3 -C 4 alkenyl, C 3 -C 4 alkynyl; C 2 -C 4 haloalkyl, C 2 -C 3 cyanoalkyl, C 3 -C 6 cycloalkyl, C 4 -C 7 cycloalkylalkyl or C 2 -C 4 alkoxyalkyl; R 20 is H, CH 3 or CH 2 CH 3 ; R 21 is CH 3 , CH 2 CH 3 , CH 2 CH 2 CH 3 , OCH 3 or OCH 2 CH 3 ; or R 20 and R 21 may be taken together to form --(CH 2 ) 2 (CH 2 ) n (CH 2 ) 2 -- and --CH 2 CH 2 OCH 2 CH 2 --; R 22 is C 1 -C 4 alkyl, C 2 -C 3 cyanoalkyl, OCH 3 , OCH 2 CH 3 , N(CH 3 ) 2 , C 3 -C 4 alkenyl, C 3 -C 4 alkynyl, cyclopropylmethyl or C 3 -C 4 cycloalkyl; R 23 is H, C 1 -C 4 alkyl or C 3 -C 4 alkenyl; or R 22 and R 23 may be taken together as --(CH 2 ) 3 --, --(CH 2 ) 4 -- or --CH 2 CH 2 OCH 2 CH 2 --; R 24 is C 1 -C 3 alkyl or C 1 -C 3 haloalkyl; R 25 is C 1 -C 3 alkyl or N(CH 3 ) 2 ; R 26 is C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 4 alkoxyalkyl, C 3 -C 4 alkenyl, C 3 -C 4 alkynyl, phenyl optionally substituted by F, Cl, Br, CH 3 or OCH 3 , or C 2 -C 4 haloalkenyl; R 27 is C 1 -C 3 alkyl; R 28 is H, C 1 -C 4 alkyl or methoxy; R 27 and R 28 may be taken together to form --(CH 2 ) 4 --, --(CH 2 ) 5 -- or --CH 2 CH 2 OCH 2 CH 2 --; R 29 and R 30 are independently H, CH 3 or CH 2 CH 3 ; R 31 is C 1 -C 4 alkyl optionally substituted with F, Cl or OCH 3 ; R 32 is CH 3 or CH 2 CH 3 ; R 33 is H, CH 3 or CH 2 CH 3 ; R 34 is C 1 -C 3 alkyl, C 3 -C 4 alkenyl or C 3 -C 4 alkynyl; Q a is O, S, S(O), S(O) 2 or NCH 3 ; Q b is O, S, or S(O) 2 ; Q c is O, S, NH, N(C 1 -C 3 alkyl), NCH 2 CH═CH 2 or NCH 2 C.tbd.CH; Q d is O, NH, N(C 1 -C 3 alkyl), NCH 2 CH═CH 2 or NCH 2 C.tbd.CH; Q e is O or NR 12 ; Q f is C(O) or S(O) 2 ; Q g is O, S, NH or N(C 1 -C 3 alkyl); n is 0 or 1; p is 0, 1 or 2; W' is O or S; E is O, S, S(O) or S(O) 2 ; Q is ##STR62## Q 1 is ##STR63## wherein Q 1 -1 through Q 1 -87 may be optionally substituted with 1 or 2 groups selected from C 1 -C 2 alkyl or C 1 -C 2 haloalkyl; R 35 is H, C 1 -C 3 alkyl or allyl; R 36 and R 37 are independently H or C 1 -C 3 alkyl; X b is O or NR 36 ; and X c is O, S, S(O), S(O) 2 or NR 36 ; A is ##STR64## X or Y is H, halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 haloalkylthio, C 1 -C 4 alkylthio, C 2 -C 5 alkoxyalkyl, C 2 -C 5 alkoxyalkoxy, amino, C 1 -C 3 alkylamino, di(C 1 -C 3 alkyl)amino, C 3 -C 4 alkenyloxy, C 3 -C 4 alkynyloxy, C 2 -C 5 alkylsulfinylalkyl, C 1 -C 4 haloalkyl, C 2 -C 5 alkylsulfonylalkyl, C 3 -C 5 cycloalkyl, C 2 -C 4 alkynyl, C 2 -C 5 alkylthioalkyl, ##STR65## or N(OCH 3 )CH 3 ; W 1 and W 2 are independently O or S; m and m' are independently 2 or 3; R a is H or CH 3 ; R b and R c are independently C 1 -C 2 alkyl; Z is CH, N, CCH 3 , CCH 2 CH 3 , CCl or CBr; Z 1 is C--U, N or N--O; Z 2 and Z 3 are independently N or C--U; Z 4 is NCH 3 , O, S or CH 2 ; U is H, F, Cl, Br, C 1 -C 2 alkyl optionally substituted by F, Cl, Br or OCH 3 , CN, NO 2 , NMe 2 , OR'", SR'" or CO 2 CH 3 ; R'" is C 1 -C 2 alkyl optionally substituted with F, Cl, Br or OCH 3 ; X a is CH 3 , CH 2 CH 3 or CH 2 CF 3 ; and X d is H or CH 3 ; and their agriculturally suitable salts; provided that (1) the total number of carbon atoms of R 22 and R 23 is less than or equal to five; (2) when X or Y is Cl, F, Br or I, then Z is CH and the remaining X or Y is OCH 3 , OCH 2 CH 3 , N(OCH 3 )CH 3 , NHCH 3 , N(CH 3 ) 2 or OCF 2 H; (3) when X or Y is C 1 haloalkoxy, then Z is CH; (4) at least one of X or Y is X' where X' is H, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkylthio, C 1 -C 4 alkylthio, C 2 -C 5 alkoxyalkoxy, amino, C 1 -C 3 alkylamino or di(C 1 -C 3 alkyl)amino; (5) the total number of carbon atoms of R 27 and R 28 is less than or equal to five; (6) when A is A-1, A-2, A-7 or A-19 then Z is a carbon value, and when A is A-3, A-4, A-5, A-6, A-8 and A-9 then Z is N; and (7) when A is A-11 then one of Z 1 , Z 2 or Z 3 is N.
Claim 3
Dependent Claim
18 words
A compound of claim 1 where A is A-1, A-2, A-4, A-6, A-7, A-8, A-9, A-11, or A-19.
Claim 4
Dependent Claim
18 words
A compound of claim 2 where Formula I is Formula Ia; W is O; and R is H.
Claim 5
Dependent Claim
16 words
A compound of claim 2 where Formula I is Formula Ib; G is OR' or SR'.
Claim 6
Dependent Claim
141 words
A compound of claim 3 where R 2 ' is H; X' is C 1 -C 2 alkyl, C 1 -C 2 alkoxy, OCF 2 H, CH 2 F, CF 3 , OCH 2 CH 2 F, OCH 2 CHF 2 , OCH 2 CF 3 , CH 2 Cl or CH 2 Br; X or Y is H, C 1 -C 2 alkyl, C 1 -C 2 alkoxy, CH 2 OCH 3 , Cl, F, Br, I, CH 2 OCH 2 CH 3 , NHCH 3 , N(OCH 3 )CH 3 , N(CH 3 ) 2 , CF 3 , SCH 3 , OCH 2 CH═CH 2 , OCH 2 C.tbd.CH, OCH 2 CH 2 OCH 3 , CH 2 SCH 3 , ##STR66## OCF 2 H, SCF 2 H, cyclopropyl, C.tbd.CH or C.tbd.CCH 3 ; and Z is CH.
Claim 7
Dependent Claim
342 words
A compound of claim 5 where R 1 is halogen; NO 2 ; CH; C 1 -C 3 alkyl optionally substituted with F, Cl, Br, CN, OCH 3 or SCH 3 ; C 3 alkenyl optionally substituted with F, Cl or Br; C 3 alkynyl; C 3 cycloalkyl optionally substituted with F, Cl or CH 3 ; C(O)R 16 ; C(OCH 2 CH 2 O)R 16 ; C(R 16 )(OR 17 )(OR 18 ); CO 2 R 19 ; C(O)NR 20 R 21 ; N 3 ; S(O) 2 NR 22 R 23 ; OS(O) 2 R 25 ; ER 26 ; (CH 2 ) n Q or (CH 2 ) n Q 1 ; R 16 is C 1 -C 3 alkyl, C 3 cycloalkyl or C 3 alkenyl; R 17 and R 18 are C 1 -C 2 alkyl; R 19 is C 1 -C 3 alkyl, C 3 alkenyl, CH 2 CH 2 F, CH 2 CH 2 Cl, CH 2 CH 2 OCH 3 or cyclopropyl methyl; R 20 is H or CH 3 ; R 21 is CH 3 , CH 2 CH 3 or OCH 3 ; R 22 is C 1 -C 3 alkyl, OCH 3 , OCH 2 CH 3 , allyl, propargyl or cyclopropyl; R 23 is H, CH 3 or CH 2 CH 3 ; R 26 is C 1 -C 3 alkyl optionally substituted by halogen, C 2 -C 3 alkoxyalkyl, allyl, propargyl or C 2 -C 3 haloalkenyl; n is 0; and Q 1 is Q 1 -1, Q 1 -4, Q 1 -5, Q 1 -7, Q 1 -10, Q 1 -11, Q 1 -12, Q 1 -17, Q 1 -19, Q 1 -20, Q 1 -24, Q 1 -25, Q 1 -27, Q 1 -28, Q 1 -36, Q 1 -38, Q 1 -46, Q 1 -47, Q 1 -54, Q 1 -56, Q 1 -59, Q 1 -60, Q 1 -63, Q 1 -71, Q 1 -74, Q 1 -76, Q 1 -78 or Q 1 -79.
Claim 8
Dependent Claim
77 words
A compound of claim 6 where R 2 is H; halogen; CN; NO 2 ; CH 3 ; CF 3 ; ER 31 ; or C 1 -C 2 alkyl substituted with C 1 -C 2 alkoxy, C 1 -C 2 haloalkoxy, C 1 -C 2 alkylthio, C 1 -C 2 haloalkylthio or CN; E is O or S; and R 31 is C 1 -C 2 alkyl optionally substituted with F, Cl or OCH 3 .
Claim 9
Dependent Claim
63 words
A compound of claim 7 where W' is O; Q e is NR 12 ; Q c is O, NH, N(C 1 -C 3 alkyl), NCH 2 CH═CH 2 , or NCH 2 C.tbd.CH; Q f is S(O) 2 ; Q g is O or S; R 11 is H or CH 3 ; and R 13 is H or CH 3 .
Claim 10
Dependent Claim
52 words
A compound of claim 8 where X' is CH 3 , OCH 3 , OCH 2 CH 3 or OCF 2 H; and X or Y is CH 3 , OCH 3 , C 2 H 5 , CH 2 OCH 3 , NHCH 3 , CH(OCH 3 ), Cl or cyclopropyl.
Claim 11
Dependent Claim
9 words
A compound of claim 9 where A is A-1.
Claim 12
Dependent Claim
9 words
A compound of claim 9 where A is A-2.
Claim 13
Dependent Claim
9 words
A compound of claim 9 where A is A-4.
Claim 14
Dependent Claim
9 words
A compound of claim 9 where A is A-6.
Claim 15
Dependent Claim
9 words
A compound of claim 9 where A is A-7.
Claim 16
Dependent Claim
9 words
A compound of claim 9 where A is A-8.
Claim 17
Dependent Claim
9 words
A compound of claim 9 where A is A-9.
Claim 18
Dependent Claim
9 words
A compound of claim 9 where A is A-11.
Claim 19
Dependent Claim
9 words
A compound of claim 9 where A is A-19.
Claim 20
Dependent Claim
39 words
A compound of claim 9 where A is A-1; L is L-1, L-3, L-4, L-5, L-6, L-7, L-8, L-9, L-11, L-12, L-13, L-14, L-15 or L-16; Z 1 is CH or N; and Z 2 is CH or N.
Claim 21
Dependent Claim
13 words
A compound of claim 19 where Z 1 and Z 2 are N.
Claim 22
Dependent Claim
42 words
A compound of claim 9 where A is A-4; L is L-1, L-3, L-4, L-5, L-6, L-7, L-8, L-9, L-11, L-12, L-13, L-14, L-15 or L-16; Z 4 is O or S; and Z 1 is N, CH or CCH 3 .
Claim 23
Dependent Claim
8 words
The compound of claim 1 which is 5,7-Dimethyl-N-[[2-(methylsulfonyl)phenyl]sulfonyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide.
Claim 24
Dependent Claim
9 words
The compound of claim 1 which is methyl 2-[[[(5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)carbonyl]amino]sulfonyl]benzoate.
Claim 25
Dependent Claim
9 words
The compound of claim 1 which is methyl 2-[[[(5,7-dimethyl[1,2,3]triazolo[1,5-a]pyrimidin-3-yl)carbonyl]amino]sulfonyl]benzoate.
Claim 26
Dependent Claim
8 words
The compound of claim 1 which is N-[[2-(1-ethyl-1H-tetrazol-5-yl)phenyl]sulfonyl]-5,7-dimethylpyrazolo[1,5-a]pyrimidine-3-carbamate.
Claim 27
Dependent Claim
8 words
The compound of claim 1 which is N-[[2-[(dimethylamino)sulfonyl]phenyl]sulfonyl]-5,7-dimethyl[1,2,3]triazolo[1,5-a]pyrimidine-3-carboxamide.
Claim 28
Dependent Claim
8 words
The compound of claim 1 which is N-[(2-chlorophenyl)sulfonyl]-5,7-dimethyl[1,2,3]triazolo[1,5-a]pyrimidine-3-carboxamide.
Claim 29
Dependent Claim
8 words
The compound of claim 1 which is N-[(2,6-dibromophenyl)sulfonyl]-5,7-dimethyl[1,2,3]triazolo[1,5-a]pyrimidine-3-carboxamide.
Claim 30
Dependent Claim
38 words
A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 1 and at least one of the following: surfactant, solid diluent, liquid diluent and mixtures of the foregoing.
Claim 31
Dependent Claim
38 words
A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 2 and at least one of the following: surfactant, solid diluent, liquid diluent and mixtures of the foregoing.
Claim 32
Dependent Claim
38 words
A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 3 and at least one of the following: surfactant, solid diluent, liquid diluent and mixtures of the foregoing.
Claim 33
Dependent Claim
38 words
A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 4 and at least one of the following: surfactant, solid diluent, liquid diluent and mixtures of the foregoing.
Claim 34
Dependent Claim
38 words
A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 5 and at least one of the following: surfactant, solid diluent, liquid diluent and mixtures of the foregoing.
Claim 35
Dependent Claim
38 words
A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 6 and at least one of the following: surfactant, solid diluent, liquid diluent and mixtures of the foregoing.
Claim 36
Dependent Claim
38 words
A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 7 and at least one of the following: surfactant, solid diluent, liquid diluent and mixtures of the foregoing.
Claim 37
Dependent Claim
38 words
A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 8 and at least one of the following: surfactant, solid diluent, liquid diluent and mixtures of the foregoing.
Claim 38
Dependent Claim
27 words
A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 1.
Claim 39
Dependent Claim
27 words
A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 2.
Claim 40
Dependent Claim
27 words
A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 3.
Claim 41
Dependent Claim
27 words
A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 4.
Claim 42
Dependent Claim
27 words
A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 5.
Claim 43
Dependent Claim
27 words
A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 6.
Claim 44
Dependent Claim
27 words
A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 7.
Claim 45
Dependent Claim
27 words
A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 8.
References Cited (Backward Citations)
EP0150974A2
Cited
US4622062A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1992-06-12 | 1992-12-12 | 1993-06-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1996-06-12 | 1996-12-12 | 1997-06-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2000-06-12 | 2000-12-12 | 2001-06-13 | $7700.00 | Window Closed / Lapsed |