Claims
- 1. A compound selected from ##STR131## wherein R is H: C.sub.1 -C.sub.3 alkyl optionally substituted with halogen; C.sub.1 C.sub.3 thioalkyl optionally substituted with halogen; benzyl optionally substituted with F, Cl, OCH.sub.3, SCH.sub.3 or NO.sub.2 ; allyl; propargyl; --C(O)(C.sub.1 -C.sub.3 alkyl); CO.sub.2 CH.sub.3 ; or CO.sub.2 CH.sub.2 CH.sub.3 ;
- G is Cl, OR' or SR';
- R' is C.sub.1 -C.sub.3 alkyl optionally substituted with halogen;
- L is
- W is O, S, NR" or NOR";
- R" is H or C.sub.1 -C'alkyl optionally substituted with halogen; ##STR132## R.sub.1 is H; halogen; NO.sub.2 ; CN; C.sub.1 -C.sub.4 alkyl optionally substituted with F, Cl, Br, CN, OCH.sub.3 or SCH.sub.3 ; C.sub.2 -C.sub.4 alkenyl optionally substituted with F, Cl, Br, OCH.sub.3 or SMe; C.sub.3 -C.sub.4 alkynyl; C.sub.3 -C.sub.5 cycloalkyl optionally substituted with F, Cl or CH.sub.3 ; C(O)R.sub.16 ; C(OCH.sub.2 CH.sub.2 O)R.sub.16 ; C(R.sub.16)(OR.sub.17)(OR.sub.18); CO.sub.2 R.sub.19 ; C(O)NR.sub.20 R.sub.21 ; N.sub.3 ; S(O).sub.2 NR.sub.22 R.sub.23 ; S(O).sub.2 OR.sub.24 ; OS(O).sub.2 R.sub.25 ; phenyl optionally substituted by F, Cl, Br, CH.sub.3 or OCH.sub.3 ; ER.sub.26 ; (CH.sub.2).sub.n Q or (CH.sub.2).sub.n Q.sub.1 ;
- R.sub.2 is H, halogen, CN, NO.sub.2, C.sub.1 -C.sub.3 alkyl optionally substituted with halogen, CO.sub.2 R.sub.19, S(O).sub.2 NR.sub.27 R.sub.28, NR.sub.29 R.sub.30, ER.sub.31 ; or C.sub.1 -C.sub.2 alkyl substituted with C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 haloalkoxy, C.sub.1 -C.sub.2 alkylthio, C.sub.1 -C.sub.2 haloalkylthio, CN, OH or SH;
- R.sub.2.sup.' is independently H, F, Cl, Br, CH.sub.3, OCH.sub.3, or SCH.sub.3 ;
- R.sub.3 is H, CH.sub.3, OCH.sub.3, OCF.sub.2 H, F, Cl, Br, CO.sub.2 R .sub.19, S(O).sub.2 N(CH.sub.3).sub.2, OS(O).sub.2 CH.sub.3 or S(O).sub.p CH.sub.3 ;
- R.sub.4 is Cl, NO.sub.2, CO.sub.2 CH.sub.3, CO.sub.2 CH.sub.2 CH.sub.3, C(O)N(CH.sub.3).sub.2, OS(O).sub.2 CH.sub.3, S(O).sub.2 CH.sub.3, S(O).sub.2 CH.sub.2 CH.sub.3, OCH.sub.3 or OCH.sub.2 CH.sub.3 ;
- R.sub.5 is H, C.sub.1 -C.sub.3 alkyl, F, Cl, Br, No.sub.2, S(O).sub.2 NR.sub.32 R.sub.33, S(O).sub.2 N(OCH.sub.3)CH.sub.3 or S(O).sub.p R.sub.34 ;
- R.sub.6 is C.sub.1 -C.sub.3 alkyl or phenyl;
- R.sub.7 is H. C.sub.1 -C.sub.3 alkyl optionally substituted with halogen, C.sub.3 -C.sub.4 alkenyl, or phenyl;
- R.sub.8 is H or CH.sub.3 ;
- R.sub.9 is H, CH.sub.3 or CH.sub.2 CH.sub.3 ;
- R.sub.10 is H, CH.sub.3 or CH.sub.2 CH.sub.3 ;
- R.sub.11 is H, Cl or C.sub.1 -C.sub.3 alkyl;
- R.sub.12 is H, C.sub.1 -C.sub.4 alkyl optionally substituted with F, Cl, Br or OCH.sub.3 ; C.sub.3 -C.sub.5 cycloalkyl optionally substituted with F, Cl or OCH.sub.3 ; C.sub.3 -C.sub.4 alkenyl; or C.sub.3 -C.sub.4 alkynyl;
- R.sub.13 is H or C.sub.1 -C.sub.3 alkyl;
- R.sub.14 is H, F, Cl, Br, CH.sub.3 or CH.sub.2 CH.sub.3 ;
- R.sub.15 is H, F, Cl, Br. CH.sub.3 or CH.sub.2 CH.sub.3 ;
- R.sub.16 is C.sub.1 -C.sub.4 alkyl optionally substituted with F, Cl, Br or OCH.sub.3 ; C.sub.3 -C.sub.5 cycloalkyl optionally substituted with F or Cl; or C.sub.3 -C.sub.4 alkenyl;
- R.sub.17 and R.sub.18 are independently C.sub.1 -C.sub.3 alkyl;
- R.sub.19 is C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl; C.sub.2 -C.sub.4 haloalkyl, C.sub.2 -C.sub.3 cyanoalkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.4 -C.sub.7 cycloalkylalkyl or C.sub.2 -C.sub.4 alkoxyalkyl;
- R.sub.20 is H, CH.sub.3 or CH.sub.2 CH.sub.3 ;
- R.sub.21 is CH.sub.3, CH.sub.2 CH.sub.3, CH.sub.2 CH.sub.2 CH.sub.3, OCH.sub.3 or OCH.sub.2 CH.sub.3 ; or R.sub.20 R.sub.21 may be taken together to form --(CH.sub.2).sub.2 (CH.sub.2).sub.n (CH.sub.2).sub.2 --and --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --;
- R.sub.22 is C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.3 cyanoalkyl, OCH.sub.3, OCH.sub.2 CH.sub.3, N(CH.sub.3).sub.2, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl, cyclopropylmethyl or C.sub.3 -C.sub.4 cycloalkyl;
- R.sub.23 is H, C.sub.1 -C.sub.4 alkyl or C.sub.3 -C.sub.4 alkenyl; or
- R.sub.22 and R.sub.23 may be taken together as --(CH.sub.2).sub.3 --, --(CH.sub.2).sub.4 -- or --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --;
- R.sub.24 is C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 haloalkyl;
- R.sub.25 is C.sub.1 -C.sub.3 alkyl or N(CH.sub.3 .sub.2 ;
- R.sub.26 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.4 alkoxyalkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl, phenyl optionally substituted by F, Cl, Br, CH.sub.3 or OCH.sub.3, or C.sub.2 -C.sub.4 haloalkenyl;
- R.sub.27 is C.sub.1 -C.sub.3 alkyl;
- R.sub.28 is H, C.sub.1 -C.sub.4 alkyl or methoxy;
- R.sub.27 and R.sub.28 may be taken together to form --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.5 -- or --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --;
- R.sub.29 and R.sub.30 are independently H, CH.sub.3 or CH.sub.2 CH.sub.3 ;
- R.sub.31 is C.sub.1 -C.sub.4 alkyl optionally substituted with F, Cl or OCH.sub.3 ;
- R.sub.32 is CH.sub.3 or CH.sub.2 CH.sub.3 ;
- R.sub.33 is H, CH.sub.3 or CH.sub.2 CH.sub.3 ;
- R.sub.34 is C.sub.1 -C.sub.3 alkyl, C.sub.3 -C.sub.4 alkenyl or C.sub.3 -C.sub.4 alkynyl;
- Q.sub.a is O, S, S(O), S(O).sub.2 or NCH.sub.3 ;
- Q.sub.b is O, S or S(O).sub.2 ;
- Q.sub.c is O, S, NH, N(C.sub.1 -C.sub.3 alkyl), NCH.sub.2 CH.dbd.CH.sub.2 or NCH.sub.2 C.tbd.CH;
- Q.sub.d is O, NH, N(C.sub.1 -C.sub.3 alkyl), NCH.sub.2 CH.dbd.CH.sub.2 or NCH.sub.2 C.tbd.CH;
- Q.sub.e is O or NR.sub.12 ;
- Q.sub.F is C(O) or S(O).sub.2 ;
- Q.sub.g is O, S, NH or N(C.sub.1 -C.sub.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).sub.2 ;
- Q is ##STR133## wherein Q.sub.1 -1 through Q.sub.1 -87 may be optionally substituted with 1 or 2 groups selected from C.sub.1 -C.sub.2 alkyl or C.sub.1 -C.sub.2 haloalkyl;
- R.sub.35 is H, C.sub.1 -C.sub.3 alkyl or allyl;
- R.sub.36 and R.sub.37 are independently H or C.sub.1 -C.sub.3 alkyl;
- X.sub.b is O or NR.sub.36 ; and
- X.sub.c is O, S, S(O), S(O).sub.2 or NR.sub.36 ;
- A is ##STR134## X or Y is H, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino, di(C.sub.1 -C.sub.3 alkyl)amino, C.sub.3 -C.sub.4 alkenyloxy, C.sub.3 -C.sub.4 alkynyloxy, C.sub.2 -C.sub.5 alkylsulfinylalkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.5 alkylsulfonylalkyl, C.sub.3 -C.sub.5 cycloalkyl, C.sub.2 -C.sub.4 alkynyl, C.sub.2 -C.sub.5 alkylthioalkyl, ##STR135## or N(OCH.sub.3)CH.sub.3 ; W.sub.1 and W.sub.2 are independently O or S;
- m and m' are independently 2 or 3;
- R.sub.a is H or CH.sub.3 ;
- R.sub.b and R.sub.c are independently C.sub.1 -C.sub.2 alkyl;
- Z is CH, N, CCH.sub.3, CCH.sub.2 CH.sub.3, CCl or CBr;
- Z.sub.1 is C-U, N or N-O;
- Z.sub.2 and Z.sub.3 are independently N or C-U;
- Z.sub.4 is NCH.sub.3, O, S or CH.sub.2 ;
- U is H, F, Cl, Br, C.sub.1 -C.sub.2 alkyl optionally substituted by F, Cl, Br or OCH.sub.3, CN, NO.sub.2, NMe.sub.2, OR'", SR'" or CO.sub.2 CH.sub.3 ;
- R''" is C.sub.1 -C.sub.2 alkyl optionally substituted with F, Cl, Br or OCH.sub.3 ;
- X.sub.a is CH.sub.3, CH.sub.2 CH.sub.3 or CH.sub.2 CF.sub.3 ; and
- X.sub.d is H or CH.sub.3 ;
- and their agriculturally suitable salts; provided that
- (1) the total number of carbon atoms of R.sub.22 and R.sub.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.sub.3, OCH.sub.2 CH.sub.3, N(OCH.sub.3)CH.sub.3, NHCH.sub.3, N(CH.sub.3).sub.2 or OCF.sub.2 H;
- (3) when X or Y is C.sub.1 haloalkoxy, then Z is CH;
- (4) at least one of X or Y is X' where X' is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino or di(C.sub.1 -C.sub.3 alkyl)amino; and
- (5) the total number of carbon atoms of R.sub.27 and R.sub.28 is less than or equal to five,
- (6) when A is A-3, A-4, A-5, A-6, A-8 or A-9 then Z is a carbon value, and
- (7) when A is A-11 all of Z.sub.1, Z.sub.2, or Z.sub.3, are carbon values
- 2. A compound of claim 1 where A is A-4, A-6, A-8, A-9 or A-11.
- 3. A compound of claim 2 where
- Formula I is Formula Ia;
- W is O; and
- R is H.
- 4. A compound of claim 2 where
- Formula I is Formula Ib;
- G is OR' or SR'.
- 5. A compound of claim 3 where
- R.sub.2.sup.' is H;
- X' is C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, OCF.sub.2 H, CH.sub.2 F, CF.sub.3, OCH.sub.2 CH.sub.2 F, OCH.sub.2 CHF.sub.2, OCH.sub.2 CF.sub.3, CH.sub.2 Cl or CH.sub.2 Br;
- X or Y is H, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, CH.sub.2 OCH.sub.3, Cl, F, Br, I, CH.sub.2 OCH.sub.2 CH.sub.3, NHCH.sub.3, N(OCH.sub.3)CH.sub.3, N(CH.sub.3).sub.2, CF.sub.3, SCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH, OCH.sub.2 CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3, ##STR136## OCF.sub.2 H, SCF.sub.2 H, cyclopropyl, C.tbd.CH or C.tbd.CCH.sub.3 ; and Z is CH.
- 6. A compound of claim 5 where
- R.sub.1 is halogen; NO.sub.2 ; CN; C.sub.1 -C.sub.3 alkyl optionally substituted with F, Cl, Br, CN, OCH.sub.3 or SCH.sub.3 ; C.sub.3 alkenyl optionally substituted with F, Cl or Br; C.sub.3 alkynyl; C.sub.3 cycloalkyl optionally substituted with F, Cl or CH.sub.3 ; C(O)R.sub.16 ; C(OCH.sub.2 CH.sub.2 O)R.sub.16 ; C(R.sub.16)(OR.sub.17)(OR.sub.18); CO.sub.2 R.sub.19 ; C(O)NR.sub.20 R.sub.21 ; N.sub.3 ; S(O).sub.2 NR.sub.22 R.sub.23 ; OS(O).sub.2 R.sub.25 ; ER.sub.26 ; (CH.sub.2).sub.n Q or (CH.sub.2).sub.n Q.sub.1 ;
- R.sub.16 is C.sub.1 -C.sub.3 alkyl, C.sub.3 cycloalkyl or C.sub.3 alkenyl;
- R.sub.17 and R.sub.18 are C.sub.1 -C.sub.2 alkyl;
- R.sub.19 is C.sub.1 -C.sub.3 alkyl, C.sub.3 alkenyl, CH.sub.2 CH.sub.2 F, CH.sub.2 CH.sub.2 Cl, CH.sub.2 CH.sub.2 OCH.sub.3 or cyclopropyl methyl;
- R.sub.20 is H or CH.sub.3 ;
- R.sub.21 is CH.sub.3, CH.sub.2 CH.sub.3 or OCH.sub.3 ;
- R.sub.22 is C.sub.1 -C.sub.3 alkyl, OCH.sub.3, OCH.sub.2 CH.sub.3, allyl, propargyl or cyclopropyl;
- R.sub.23 is H, CH.sub.3 or CH.sub.2 CH.sub.3 ;
- R.sub.26 is C.sub.1 -C.sub.3 alkyl optionally substituted by halogen, C.sub.2 -C.sub.3 alkoxyalkyl, allyl, propargyl or C.sub.2 -C.sub.3 haloalkenyl;
- n is 0; and
- Q.sub.1 is Q.sub.1 -1, Q.sub.1 -4, Q.sub.1 -5, Q.sub.1 -7, Q.sub.1 -10, Q.sub.1 -11, Q.sub.1 -12, Q.sub.1 -17, Q.sub.1 -19, Q.sub.1 -20, Q.sub.1 -24, Q.sub.1 -25, Q.sub.1 -27, Q.sub.1 -28, Q.sub.1 -36, Q.sub.1 -38, Q.sub.1 -46, Q.sub.1 -47, Q.sub.1 -54, Q.sub.1 -56, Q.sub.1 -59, Q.sub.1 -60, Q.sub.1 -63, Q.sub.1 -71, Q.sub.1 -74, Q.sub.1 -76, Q.sub.1 -78 or Q.sub.1 -79.
- 7. A compound of claim 6 where
- R.sub.2 is H; halogen; CN; NO.sub.2 ; CH.sub.3 ; CF.sub.3 ; ER.sub.31 ; or C.sub.1 -C.sub.2 alkyl substituted with C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 haloalkoxy, C.sub.1 -C.sub.2 alkylthio, C.sub.1 -C.sub.2 haloalkylthio or CN;
- E is O or S; and
- R.sub.31 is C.sub.1 -C.sub.2 alkyl optionally substituted with F, Cl or OCH.sub.3.
- 8. A compound of claim 7 where
- W' is O;
- Q.sub.e is NR.sub.12 ;
- Q.sub.c is O, NH, N(C.sub.1 -C.sub.3 alkyl), NCH.sub.2 CH.dbd.CH.sub.2, or NCH.sub.2 C.tbd.CH;
- Q.sub.f is S(O).sub.2 ;
- Q.sub.g is O or S;
- R.sub.11 is H or CH.sub.3 ; and
- R.sub.13 is H or CH.sub.3.
- 9. A compound of claim 8 where
- X' is CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3 or OCF.sub.2 H; and
- X or Y is CH.sub.3, OCH.sub.3, C.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, NHCH.sub.3, CH(OCH.sub.3).sub.2, Cl or cyclopropyl.
- 10. A compound of claim 9 where A is A-4.
- 11. A compound of claim 9 where A is A-6.
- 12. A compound of claim 9 where A is A-8.
- 13. A compound of claim 9 where A is A-9.
- 14. A compound of claim 9 where A is A-11.
- 15. 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.sub.1 is CH or N; and
- Z.sub.2 is CH or N.
- 16. A compound of claim 15 where Z.sub.1 and Z.sub.2 are N.
- 17. 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.sub.4 is O or S; and
- Z.sub.1 is N, CH or CCH.sub.3.
- 18. The compound of claim 1 which is methyl 2-[[[5,7-dimethyl)[1H]pyrrolo[3,2-3-yl)carbonyl]amino]sulfonyl]benzoate.
- 19. 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.
- 20. 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.
- 21. 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.
- 22. 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.
- 23. 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.
- 24. 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.
- 25. 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.
- 26. 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.
- 27. 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.
- 28. 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.
- 29. 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.
- 30. 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.
- 31. 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.
- 32. 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.
- 33. 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.
- 34. 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.
RELATED APPLICATION
This is a division of application Ser. No. 101,314, filed Sept. 25, 1987, now U.S. Pat. No. 4,838,925, which is a continuation-in-part of my copending application U.S. Ser. No. 022,279, filed Mar. 17, 1987, now abandoned, which in turn is a continuation-in-part of U.S. Ser. No. 892,062, filed Aug. 1, 1986, now abandoned, which in turn is a continuation-in-part of U.S. Ser. No. 856,511 filed Apr. 25, 1986 now abandoned.
Foreign Referenced Citations (1)
Number |
Date |
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0142152 |
May 1985 |
EPX |
Divisions (1)
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Number |
Date |
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Parent |
101314 |
Sep 1987 |
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Continuation in Parts (3)
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Number |
Date |
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22279 |
Mar 1987 |
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Parent |
892062 |
Aug 1986 |
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Parent |
856511 |
Apr 1986 |
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