Claims
- 1. A compound of Formula I or II: ##STR116## wherein: Q is selected from the group ##STR117## A and E are taken together to form --CH.sub.2 --, --CH.sub.2 CH.sub.2 --, substituted --CH.sub.2 --, and substituted --CH.sub.2 CH.sub.2 -- the substituents independently selected from 1-2 halogen and 1-2 methyl;
- G is selected from the group ##STR118## X is selected from the group O, S and N--X.sup.2 ; X.sup.1 is selected from the group Cl, Br, OR.sup.8, SR.sup.8 and NR.sup.8 R.sup.9 ;
- X.sup.2 is selected from the group R.sup.8, OH, OR.sup.8, CN, SO.sub.2 R.sup.8, SO.sub.2 Ph, OC(O)NR.sup.9 R.sup.10, OC(O)OR.sup.8, NR.sup.9 R.sup.10 and phenyl optionally substituted with R.sup.11 ;
- Y is selected from the group H; C.sub.1 -C.sub.6 alkyl; benzyl; C.sub.2 -C.sub.6 alkoxyalkyl; C.sub.2 -C.sub.6 alkenyl; C.sub.2 -C.sub.6 alkynyl; C.sub.1 -C.sub.6 alkyl optionally substituted by halogen, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 haloalkoxy, CN, NO.sub.2, S(O).sub.r R.sup.32, COR.sup.32, CO.sub.2 R.sup.32, phenyl optionally substituted by halogen, CN, C.sub.1 -C.sub.2 haloalkyl and C.sub.1 -C.sub.2 haloalkoxy; C.sub.3 -C.sub.6 cycloalkyl; C.sub.3 -C.sub.6 cyclohaloalkyl; C.sub.3 -C.sub.6 cycloalkylalkyl; CHO; C.sub.2 -C.sub.6 alkylcarbonyl; C.sub.2 -C.sub.6 alkoxycarbonyl; C.sub.2 -C.sub.6 haloalkylcarbonyl; COR.sup.36 ; CO.sub.2 R.sup.36 ; C.sub.1 -C.sub.6 alkylthio; C.sub.1 -C.sub.6 haloalkylthio; phenylthio; R.sup.12 OC(O)N(R.sup.13)S-- and R.sup.14 (R.sup.15)NS--;
- A.sup.1 is H;
- A.sup.1 and Y can be taken together to form --(CH.sub.2).sub.t --;
- Z is C;
- Z.sup.1 is O;
- R.sup.1 and R.sup.2 are independently selected from the group H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 haloalkenyl, C.sub.2 -C.sub.6 alkynyl, C.sub.3 -C.sub.6 haloalkynyl, C.sub.2 -C.sub.6 alkoxyalkyl, C.sub.2 -C.sub.6 alkylthioalkyl, C.sub.1 -C.sub.6 nitroalkyl, C.sub.2 -C.sub.6 cyanoalkyl, C.sub.3 -C.sub.8 alkoxycarbonylalkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.3 -C.sub.6 halocycloalkyl, halogen, CN, N.sub.3, SCN, NO.sub.2, OR.sup.17, SR.sup.17, S(O)R.sup.17, S(O).sub.2 R.sup.17, OC(O)R.sup.17, OS(O).sub.2 R.sup.17, CO.sub.2 R.sup.17, C(O)R.sup.17, C(O)NR.sup.17 R.sup.18, SO.sub.2 NR.sup.17 R.sup.18, NR.sup.17 R.sup.18, NR.sup.18 C(O)R.sup.17, OC(O)NHR.sup.17, NR.sup.18 C(O)NHR.sup.17, NR.sup.18 SO.sub.2 R.sup.17, phenyl optionally substituted with 1 to 3 substituents independently selected from W, and benzyl optionally substituted with 1 to 3 substituents independently selected from W; or when m or n is 2, (R.sup.1).sub.2 can be taken together, or (R.sup.2).sub.2 can be taken together as --OCH.sub.2 O--, --OCF.sub.2 O--, --OCH.sub.2 CH.sub.2 O--, --CH.sub.2 C(CH.sub.3).sub.2 O--, --CF.sub.2 CF.sub.2 O or --OCF.sub.2 CF.sub.2 O-- to form a cyclic bridge; provided that when R.sup.1 or R.sup.2 is S(O)R.sup.17, S(O).sub.2 R.sup.17, OC(O)R.sup.17 or OS(O).sub.2 R.sup.17 then R.sup.17 is other than H;
- R.sup.3 is selected from the group H, halogen, N(R.sup.22)R.sup.23, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 haloalkenyl, C.sub.2 -C.sub.6 alkynyl, C.sub.2 -C.sub.6 alkoxylalkyl, CO.sub.2 R.sup.17, C(O)R.sup.17, C(O)NR.sup.17 R.sup.18, phenyl, phenyl substituted with 1 to 3 substituents independently selected from halogen, C.sub.1 -C.sub.6 haloalkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 haloalkenyl, C.sub.2 -C.sub.6 alkynyl, C.sub.3 -C.sub.6 haloalkynyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.3 -C.sub.6 halocycloalkyl, CN, SCN, NO.sub.2, OR.sup.17, SR.sup.17, CO.sub.2 R.sup.17, C(O)R.sup.17, C(O)NR.sup.17 R.sup.18 and SO.sub.2 NR.sup.17 R.sup.18 benzyl and benzyl substituted with 1 to 3 substituents independently selected from halogen;
- R.sup.4 and R.sup.5 are independently selected from the group H, C.sub.1 -C.sub.4 alkyl, COR.sup.20 and C.sub.2 -C.sub.4 alkoxycarbonyl; or R.sup.4 and R.sup.5 can be taken together to form .dbd.O or .dbd.S;
- R.sup.6 is selected from the group H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.4 alkylcarbonyl, C.sub.2 -C.sub.4 haloalkoxycarbonyl, C.sub.2 -C.sub.4 alkoxycarbonyl C.sub.2 -C.sub.4 haloalkoxycarbonyl, COR.sup.36, CO.sub.2 R.sup.36, C.sub.2 -C.sub.5 alkylaminocarbonyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.3 -C.sub.6 halocycloalkyl, C.sub.4 -C.sub.7 alkylcycloalkyl, C.sub.4 -C.sub.7 haloalkylcycloalkyl, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.1 -C.sub.4 haloalkylsulfonyl and SO.sub.2 Ph optionally substituted with Cl, Br or CH.sub.3 ;
- R.sup.8 is selected from the group C.sub.1 -C.sub.3 alkyl, C.sub.2 -C.sub.4 alkenyl, C.sub.2 -C.sub.4 alkynyl, C.sub.1 -C.sub.3 haloalkyl, C.sub.2 -C.sub.4 haloalkenyl, C.sub.3 -C.sub.6 cycloalkyl; C.sub.1 -C.sub.3 alkyl substituted with OCH.sub.3, OCH.sub.2 CH.sub.3, NO.sub.2, CN, CO.sub.2 CH.sub.3, CO.sub.2 CH.sub.2 CH.sub.3, SCH.sub.3 or SCH.sub.2 CH.sub.3 and benzyl optionally substituted with R.sup.11 ;
- R.sup.9 is selected from the group H, C.sub.1 -C.sub.4 alkyl C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.4 alkoxycarbonyl, and optionally substituted phenyl and pyridine wherein the substituent(s) are selected from R.sup.15 ; or
- R.sup.8 and R.sup.9 can 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 -- each of which is optionally and independently substituted with 1 or 2 CH.sub.3 groups;
- R.sup.10 is selected from the group H and C.sub.1 -C.sub.4 alkyl; or
- R.sup.9 and R.sup.10 can 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 -- each of which is optionally and independently substituted with 1 or 2 CH.sub.3 groups;
- R.sup.11 is selected from halogen, CN, C.sub.1 -C.sub.3 haloalkyl and C.sub.1 -C.sub.3 haloalkoxy;
- R.sup.12 is C.sub.1 -C.sub.6 alkyl;
- R.sup.13 is C.sub.1 -C.sub.4 alkyl;
- R.sup.14 and R.sup.15 are independently C.sub.1 -C.sub.4 alkyl; or
- R.sup.14 and R.sup.15 can be taken together as --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 -- or --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --;
- R.sup.17 is selected from the group H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 haloalkenyl, C.sub.2 -C.sub.6 alkynyl, C.sub.3 -C.sub.6 haloalkynyl, C.sub.2 -C.sub.6 alkoxyalkyl, C.sub.2 -C.sub.6 alkylthioalkyl, C.sub.1 -C.sub.6 nitroalkyl, C.sub.2 -C.sub.6 cyanoalkyl, C.sub.3 -C.sub.8 alkoxycarbonylalkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.3 -C.sub.6 halocycloalkyl, and optionally substituted phenyl and benzyl wherein the substituents are 1 to 3 substituents independently selected from W;
- R.sup.18 is selected from the group H and C.sub.1 -C.sub.4 alkyl; or
- R.sup.17 and R.sup.18, when attached to the same atom, can be taken together as --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.5 --, or --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --;
- R.sup.20 is C.sub.1 -C.sub.3 alkyl;
- R.sup.22 is selected from the group H, C.sub.2 -C.sub.7 alkylcarbonyl, C.sub.2 -C.sub.7 alkoxycarbonyl, optionally substituted C.sub.1 -C.sub.4 alkyl, optionally substituted C.sub.2 -C.sub.4 alkenyl, and optionally substituted C.sub.2 -C.sub.4 alkynyl, the substituents selected from C.sub.1 -C.sub.2 alkoxy, CN, C(O)R.sup.30 and C(O).sub.2 R.sup.27 ;
- R.sup.23 is selected from the group H, C.sub.1 -C.sub.3 alkyl, phenyl, phenyl substituted with W, benzyl and benzyl substituted with W;
- R.sup.27 is selected from the group C.sub.1 -C.sub.3 alkyl, phenyl and phenyl substituted with W;
- R.sup.30 is selected from the group H, C.sub.1 -C.sub.3 alkyl, phenyl and phenyl substituted by W;
- R.sup.32 is selected from the group C.sub.1 -C.sub.3 alkyl;
- R.sup.36 is selected from the group phenyl and phenyl substituted by W;
- W is selected from the group halogen, CN, NO.sub.2, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 haloalkyl, 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, C.sub.1 -C.sub.2 alkylsulfonyl and C.sub.1 -C.sub.2 haloalkylsulfonyl;
- m is 1 to 3;
- n is 1 to 3;
- r is 0, 1 or 2;
- t is 2 or 3; and
- u is 1 or 2.
- 2. A compound according to claim 1 wherein:
- R.sup.1 is selected from the group H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 haloalkenyl, C.sub.2 -C.sub.6 alkynyl, C.sub.3 -C.sub.6 haloalkynyl, C.sub.2 -C.sub.6 alkoxyalkyl, C.sub.2 -C.sub.6 alkylthioalkyl, C.sub.1 -C.sub.6 nitroalkyl, C.sub.2 -C.sub.6 cyanoalkyl, C.sub.3 -C.sub.8 alkoxycarbonylalkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.3 -C.sub.6 halocycloalkyl, halogen, CN, SCN, NO.sub.2, OR.sup.17, SR.sup.17, SO.sub.2 R.sup.17, CO.sub.2 R.sup.17, C(O)R.sup.17, phenyl optionally substituted with 1 to 3 substituents independently selected from W, and benzyl optionally substituted with 1 to 3 substituents independently selected from W; with one R.sup.1 substituent in the 4-position, or when m is 2 then (R.sup.1).sub.2 can be taken together as --CH.sub.2 C(CH.sub.3).sub.2 O--, --OCH.sub.2 CH.sub.2 O--, --OCF.sub.2 CF.sub.2 O--, or --CF.sub.2 CF.sub.2 O-- to form a 5- or 6-membered fused ring;
- R.sup.2 is selected from the group H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 haloalkenyl, C.sub.2 -C.sub.6 alkynyl, C.sub.3 -C.sub.6 haloalkynyl, C.sub.2 -C.sub.6 alkoxyalkyl, C.sub.2 -C.sub.6 alkylthioalkyl, C.sub.1 -C.sub.6 nitroalkyl, C.sub.2 -C.sub.6 cyanoalkyl, C.sub.3 -C.sub.8 alkoxycarbonylalkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.3 -C.sub.6 halocycloalkyl, halogen, CN, SCN, NO.sub.2, OR.sup.17, SR.sup.17, S(O).sub.2 R.sup.17, OC(O)R.sup.17, OS(O).sub.2 R.sup.17, CO.sub.2 R.sup.17, C(O)R.sup.17, C(O)NR.sup.17 R.sup.18, SO.sub.2 NR.sup.17 R.sup.18, NR.sup.17 R.sup.18, phenyl optionally substituted with 1 to 3 substituents independently selected from W, and benzyl optionally substituted with 1 to 3 substituents independently selected from W;
- R.sup.3 is selected from the group H, C.sub.1 -C.sub.4 alkyl, CO.sub.2 R.sup.17, C(O)R.sup.17, phenyl and phenyl substituted by 1 to 3 substituents independently selected from halogen;
- R.sup.17 is selected from the group C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.2 haloalkyl, C.sub.3 -C.sub.4 alkenyl and propargyl;
- R.sup.18 is selected from the group H and CH.sub.3 ;
- X.sup.1 is selected from the group Cl, OR.sup.8, SR.sup.8 and N(CH.sub.3).sub.2 ;
- X.sup.2 is selected from the group R.sup.8, OR.sup.8 and N(CH.sub.3).sub.2 ;
- m is 1 or 2; and
- n is 1 or 2.
- 3. A compound according to claim 2 wherein G is selected from the group G-2 and G-9.
- 4. A compound according to claim 3 wherein A and E are taken together to form --CH.sub.2 --, or --CH.sub.2 CH.sub.2 --.
- 5. A compound according to claim 4 wherein Q is Q-1.
- 6. A compound according to claim 4 wherein Q is Q-2.
- 7. A compound according to claim 4 wherein Y is C.sub.1 -C.sub.6 alkyl.
- 8. A compound according to claim 5 wherein Y is CO.sub.2 R.sup.17 and R.sup.3 is CO.sub.2 R.sup.17.
- 9. A compound according to claim 1:
- methyl 7-chloro-2,3-dihydro-2-[[4-trifluoromethoxy)phenylamino]carbonyl]indeno[1,2-e]-[1,3,4]oxadiazine-4a(5H)-carboxylate.
- 10. A compound according to claim 1:
- methyl 7-chloro-2,5-dihydro-2-[N-methyl-N-[4-(trifluoromethoxy)phenyl]aminocarbonyl]indeno-[1,2-e][1,3,4]oxadiazine-4a(3H)-carboxylate.
- 11. A compound according to claim 1:
- methyl 7-chloro-2,5-dihydro-2-[[N-methyl-N-[4-trifluoromethyl)phenyl]amino]carbonyl]indeno-[1,2-e][1,3,4]oxadiazine-4a(3H)-carboxylate.
- 12. A compound according to claim 1:
- 7-fluoro-4a-(4-fluorophenyl)-4a,5-dihydro-N-[4-(trifluoromethoxy)phenyl]indeno[1,2-e][1,3,4]-oxadiazine-2(3H)-carboxamide.
- 13. A compound according to claim 1:
- 7-chloro-4a,5-dihydro-4a-methyl-N-[4-(trifluoro-methoxy)phenyl]indeno[1,2-e][1,3,4]oxadiazine-2(3H)-carboxamide.
- 14. A compound according to claim 8: methyl 7-chloro-2,5-dihydro-2-[N-(methoxycarbonyl)-N-[4-(trifluoromethoxy)phenyl aminocarbonyl]indeno[1,2-e][1,3,4]oxadiazine-4a(3H)-carboxylate.
- 15. An arthropodicidal composition comprising a compound according to any one of claims 1 to 13 and claim 14 and a carrier therefor.
- 16. A method for controlling arthropods comprising contacting them or their environment with an arthropodicidally effective amount of a compound according to any one of claims 1 to 13 and claim 14, said arthropods selected from the group household, foliar, and soil-inhabiting agronomic and nonagronomic pests.
Parent Case Info
This is the national stage of PCT/U.S. Ser. No. 91/09164, filed Dec. 17, 1991 which is a continuation of Ser. No. 07/714,401, filed Jun. 11, 1991, now abandoned, which is a continuation of Ser. No. 07/632,438, filed Dec. 21, 1990, now abandoned.
PCT Information
Filing Document |
Filing Date |
Country |
Kind |
102e Date |
371c Date |
PCT/US91/09164 |
12/21/1990 |
|
|
6/18/1993 |
6/18/1993 |
Publishing Document |
Publishing Date |
Country |
Kind |
WO92/11249 |
9/7/1992 |
|
|
US Referenced Citations (3)
Foreign Referenced Citations (1)
Number |
Date |
Country |
0286346 |
Oct 1988 |
EPX |
Continuations (2)
|
Number |
Date |
Country |
Parent |
714401 |
Jun 1991 |
|
Parent |
632438 |
Dec 1990 |
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