Claims
- 1. A bicyclic imide of formula I ##STR151## wherein the bond linking C-7 and C-8 may be single or double; m is 1-7;
- R.sup.A can occupy one or more of the 2 or 6-8 positions and is independently selected from the group: hydroxy, halogen CN OR.sup.3, (C.sub.1 -C.sub.4) alkyl, S(O).sub.n R.sup.3, COR.sup.3, and C(O)SR.sup.3 ;
- Q is ##STR152## wherein R.sup.3 is (C.sub.1 -C.sub.8)alkyl, (C.sub.3 -C.sub.8)cycloalkyl, (C.sub.3 -C.sub.8)alkenyl, (C.sub.3 -C.sub.8)alkynyl, (C.sub.1 -C.sub.8)haloalkyl, (C.sub.2 -C.sub.8) alkoxyalkyl, (C.sub.2 -C.sub.4)carboxy alkyl, (C.sub.3 -C.sub.8)alkoxycarbonylalkyl, (C.sub.4 -C.sub.8)alkenyloxyalkyl, (C.sub.4 -C.sub.8)alkynyloxyalkyl, (C.sub.3 -C.sub.8)haloalkoxyalkyl, (C.sub.3 -C.sub.8)trialkylsilyl, (C.sub.3 -C.sub.8)cyanoalkyl, (C.sub.3 -C.sub.8)haloalkenyl, (C.sub.3 -C.sub.8)haloalkynyl, (C.sub.2 -C.sub.8)alkylcarbonyl, (C.sub.2 -C.sub.8)alkoxycarbonyl, (C.sub.2 -C.sub.8)haloalkoxycarbonyl, P(O)(OR.sup.17).sub.2, CHR.sup.16 P(O)(OR.sup.17).sub.2 or CHR.sup.16 P(S)(OR.sup.17).sub.2, phenyl or benzyl optionally substituted with halogen, (C.sub.1 -C.sub.3)alkyl, (C.sub.1 -C.sub.3)haloalkyl or (C.sub.1 -C.sub.4)alkoxy;
- R.sup.4 is hydrogen or halogen;
- R.sup.5 is (C.sub.1 -C.sub.2)alkyl, (C.sub.1 -C.sub.2)haloalkyl, OCH.sub.3, SCH.sub.3, OCHF.sub.2, halogen, CN or NO.sub.2 ;
- R.sup.6 is hydrogen, (C.sub.1 -C.sub.8)alkyl, (C.sub.1 -C.sub.8)haloalkyl, halogen, OR.sup.10, S(O).sub.n R.sup.10, COR.sup.10, (O)SR.sup.10, C(O)NR.sup.11 R.sup.12, CHO, CH.dbd.CHCO.sub.2 R.sup.10, CO.sub.2 N.dbd.CR.sup.13 R.sup.14, NO.sub.2, CN, NHSO.sub.2 R.sup.15 or NHSO.sub.2 NHR.sup.15 ;
- R.sup.7 and R.sup.8 are independently hydrogen, (C.sub.1 -C.sub.3)alkyl, (C.sub.1 -C.sub.3)haloalkyl or halogen; when Q is Q-2 or Q-6, R.sup.7 and R.sup.8 together with the carbon to which they are attached may be C.dbd.O;
- R.sup.10 is (C.sub.1 -C.sub.8)alkyl, (C.sub.3 -C.sub.8) cycloalkyl, (C.sub.3 -C.sub.8)alkenyl, (C.sub.3 -C.sub.8)alkynyl, (C.sub.1 -C.sub.8)haloalkyl, (C.sub.2 -C.sub.8)alkoxyalkyl, (C.sub.2 -C.sub.6)alkylthioalkyl, (C.sub.2 -C.sub.8)alkylsulfinylalkyl, (C.sub.2 -C.sub.8)alkylsulfonylalkyl, (C.sub.3 -C.sub.8)alkoxyalkoxyalkyl, (C.sub.4 -C.sub.8)cycloalkylalkyl, (C.sub.2 -C.sub.4)carboxyalkyl, (C.sub.3 -C.sub.8)alkoxycarbonylalkyl, (C.sub.6 -C.sub.8)alkenyloxycarbonylalkyl, (C.sub.6 -C.sub.8)alkynyloxycarbonylalkyl, (C.sub.6 -C.sub.8)cycloalkoxyalkyl, (C.sub.4 -C.sub.8)alkenyloxyalkyl, (C.sub.4 -C.sub.8)alkynyloxyalkyl, (C.sub.3 -C.sub.8)haloalkoxyalkyl, (C.sub.4 -C.sub.8)haloalkenyloxyalkyl, (C.sub.4 -C.sub.8)haloalkynyloxyalkyl, (C.sub.6 -C.sub.8)cycloalkylthioalkyl, (C.sub.4 -C.sub.8)alkenylthioalkyl, (C.sub.4 -C.sub.8)alkynylthioalkyl, (C.sub.4 -C.sub.8)trialkylsilylalkyl, (C.sub.3 -C.sub.8)cyanoalkyl, (C.sub.3 -C.sub.8)halocycloalkyl, (C.sub.3 -C.sub.8)haloalkenyl, (C.sub.5 -C.sub.8)alkoxyalkenyl, (C.sub.5 -C.sub.8)haloalkoxyalkenyl, (C.sub.5 -C.sub.8)alkylthioalkenyl, (C.sub.3 -C.sub.8)haloalkynyl, (C.sub.5 -C.sub.8)alkoxyalkynyl, (C.sub.5 -C.sub.8)haloalkoxyalkynyl, (C.sub.5 -C.sub.8)alkylthioalkynyl, (C.sub.2 -C.sub.8)alkylcarbonyl, CHR.sup.16 COR.sup.17, CHR.sup.16 P(O)(OR.sup.17).sub.2, P(O)(OR.sup.17).sub.2, CHR.sup.16 P(S)(OR.sup.17).sub.2, CHR.sup.16 C(O)NR.sup.11 R.sup.12, CHR.sup.16 C(O)NH.sub.2, (C.sub.1 -C.sub.4)alkyl substituted with phenoxy or benzyloxy optionally substituted with halogen, (C.sub.1 -C.sub.3)alkyl or (C.sub.1 -C.sub.3)haloalky; benzyl optionally substituted with halogen, (C.sub.1 -C.sub.3)alkyl or (C.sub.1 -C.sub.3)haloalkyl; or phenyl optionally substituted with halogen, (C.sub.1 -C.sub.3)alkyl, (C.sub.1 -C.sub.3)haloalkyl or (C.sub.1 -C.sub.4)alkoxy;
- R.sup.11 and R.sup.13 are independently hydrogen or (C.sub.1 -C.sub.4)alkyl;
- R.sup.12 and R.sup.14 are independently (C.sub.1 -C.sub.4)alkyl, or phenyl optionally substituted with halogen, (C.sub.1 -C.sub.3)alkyl, (C.sub.1 -C.sub.3)haloalkyl or (C.sub.1 -C.sub.4)alkoxy;
- R.sup.11 and R.sup.12 may be taken together as --(CH.sub.2).sub.5 --, or --(CH.sub.2).sub.4 --, in which optionally one or more H-atoms may be replaced by (C.sub.1 -C.sub.3)alkyl, phenyl or benzyl;
- R.sup.13 and R.sup.14 may be taken together with the carbon to which they are attached to form (C.sub.3 -C.sub.[)cycloalkyl;
- R.sup.15 is (C.sub.1 -C.sub.4)alkyl or (C.sub.1 -C.sub.4)haloalkyl;
- R.sup.16 is hydrogen or (C.sub.1 -C.sub.3)alkyl;
- R.sup.17 is (C.sub.1 -C.sub.6)alkyl, (C.sub.3 -C.sub.6)alkenyl Or (C.sub.3 -C.sub.6)alkynyl;
- W is 0 or S;
- n is 0, 1 or 2;
- provided that when Q is not fused to a ring bridging the 5'- and 6'-position and C-7 and C-8 are linked by a single bond, then at least one R.sup.A is other than hydroxy, halogen, (C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4) alkoxy.
- 2. A bicyclic imide selected from the group consisting of 4-[4'-chloro-2'-fluoro-5'-(prop-2-ynyloxy)phenyl]-3,5-dioxo-7-fluoro-1,4-diazobicyclo-[3.3.0]octane, 4-[4'-chloro-2'-fluoro-5'-(1-methyl-prop-2-ynyloxy)phenyl]-3,5-dioxo-7-fluoro-1,4-diazabicyclo[3.3.0]octane, 4-[4'-chloro-2'-fluoro-5'-(2-propynyloxy)phenyl]-3,5-dioxo-7-chloro-1,4-diazabicyclo[3.3.0]octane, 4-[4'-chloro-2'-fluoro-5'-(1-methylethoxy)phenyl]-3,5-dioxo-7,7-difluoro-1,4-diazabicyclo[3.3.0]octane and any stereoisomer thereof.
- 3. A bicyclic imide according to claim 1 or 2, characterized in that at least one R.sup.A is in the 7-position.
- 4. A bicyclic imide according to claim 3, characterized in that at least one R.sup.A in the 7-position is fluoro, chloro or bromo.
- 5. A bicyclic imide according to any one of claims 1 to 4, characterized in that it has 2R-configuration.
- 6. A composition for controlling weeds comprising an effective amount of a compound of claim 1 or 2 and at least one carrier therefor.
- 7. A method for controlling weeds comprising applying to the locus to be protected an effective amount of a compound of claim 1 or 2.
- 8. A method for controlling weeds in plantation crops comprising applying to the locus to be protected an effective amount of a compound of formula Ia: ##STR153## wherein the bond linking C-7 and C-8 may be single or double; m is 1-7;
- R.sup.A can occupy one or more of the 2 or 6-8 positions and is independently selected from the group: hydroxy, halogen, CN, OR.sup.3, (C.sub.1 -C.sub.4)alkyl, S(O).sub.n R.sup.3, COR.sup.3, and C(O)SR.sup.3 ;
- Q is ##STR154## wherein R.sup.3 is (C.sub.1 -C.sub.8)alkyl, (C.sub.3 -C.sub.8)cycloalkyl, (C.sub.3 -C.sub.8)alkenyl, (C.sub.3 -C.sub.8)alkynyl, (C.sub.1 -C.sub.8)haloalkyl, (C.sub.2 -C.sub.8)alkoxyalkyl, (C.sub.2 -C.sub.4)carboxy alkyl, (C.sub.3 -C.sub.8)alkoxycarbonylalkyl, (C.sub.4 -C.sub.8)alkenyloxyalkyl, (C.sub.4 -C.sub.8)alkynyloxyalkyl, (C.sub.3 -C.sub.8)haloalkoxyalkyl, (C.sub.3 -C.sub.8)trialkylsilyl, (C.sub.3 -C.sub.8)cyanoalkyl, (C.sub.3 -C.sub.8)haloalkenyl, (C.sub.3 -C.sub.8)haloalkynyl, (C.sub.2 -C.sub.8)alkylcarbonyl, (C.sub.2 -C.sub.8)alkoxycarbonyl, (C.sub.2 -C.sub.8)haloalkoxycarbonyl, P(O))(OR.sup.17).sub.2, CHR.sup.16 P(O)(OR.sup.17).sub.2 or CHR.sup.16 P(S)(OR.sup.17).sub.2, phenyl or benzyl optionally substituted with halogen, (C.sub.1 -C.sub.3)alkyl, (C.sub.1 -C.sub.3)haloalkyl or (C.sub.1 -C.sub.4)alkoxy;
- R.sup.4 is hydrogen or halogen;
- R.sup.5 is (C.sub.1 -C.sub.2)alkyl, (C.sub.1 -C.sub.2)haloalkyl, OCH.sub.3, SCH.sub.3, OCHF.sub.2, halogen, CN or NO.sub.2 ;
- R.sup.6 i s hydrogen, (C.sub.1 -C.sub.8)alkyl, (C.sub.1 -C.sub.8)haloalkyl, halogen, OR.sup.10, S(O).sub.n R.sup.10, COR.sup.10, C(O)SR.sup.10, C(O)NR.sup.11 R.sup.12, CHO CH.dbd.CHCO.sub.2 R.sup.10, CO.sub.2 N.dbd.CR.sup.13 R.sup.14, NO.sub.2, CN, NHSO.sub.2 R.sup.15 or NHSO.sub.2 NHR.sup.15 ;
- R.sup.7 and R.sup.8 are independently hydrogen, (C.sub.1 -C.sub.3)alkyl, (C.sub.1 -C.sub.3)haloalkyl or halogen; when Q is Q-2 or Q-6, R.sup.7 and R.sup.8 together with the carbon to which they are attached may be C.dbd.O;
- R.sup.10 is (C.sub.1 -C.sub.8)alkyl (C.sub.3 -C.sub.8)cycloalkyl, (C.sub.3 -C.sub.8)alkenyl, (C.sub.3 -C.sub.8)alkynyl, (C.sub.1 -C.sub.8)haloalkyl, (C.sub.2 -C.sub.8)alkoxyalkyl, (C.sub.2 -C.sub.6)alkylthioalkyl, (C.sub.2 -C.sub.8)alkylsulfinylalkyl, (C.sub.2 -C.sub.8)alkylsulfonylalkyl, (C.sub.3 -C.sub.8)alkoxyalkoxyalkyl, (C.sub.4 -C.sub.8)cycloalkylalkyl, (C.sub.2 -C.sub.4)carboxyalkyl, (C.sub.3 -C.sub.8)alkoxycarbonylalkyl, (C.sub.6 -C.sub.8)alkenyloxycarbonylalkyl, (C.sub.6 -C.sub.8)alkynyloxycarbonylalkyl, (C.sub.6 -C.sub.8)cycloalkoxyalkyl, (C.sub.4 -C.sub.8)alkenyloxyalkyl, (C.sub.4 -C.sub.8)alkynyloxyalkyl, (C.sub.3 -C.sub.8)haloalkoxyalkyl, (C.sub.4 -C.sub.8)haloalkenyloxyalkyl, (C.sub.4 -C.sub.8)haloalkynyloxyalkyl, (C.sub.6 -C.sub.8)cycloalkylthioalkyl, (C.sub.4 -C.sub.8)alkenylthioalkyl, (C.sub.4 -C.sub.8)alkynylthioalkyl, (C.sub.4 -C.sub.8)trialkylsilylalkyl, (C.sub.3 -C.sub.8)cyanoalkyl, (C.sub.3 -C.sub.8)halocycloalkyl, (C.sub.3 -C.sub.8)haloalkenyl, (C.sub.5 -C.sub.8)alkoxyalkenyl, (C.sub.5 -C.sub.8)haloalkoxyalkenyl, (C.sub.5 -C.sub.8)alkylthioalkenyl, (C.sub.3 -C.sub.8)haloalkynyl, (C.sub.5 -C.sub.8)alkoxyalkynyl, ](C.sub.5 -C.sub.8)haloalkoxyalkynyl, (C.sub.5 -C.sub.8)alkylthioalkynyl, (C.sub.2 -C.sub.8)alkylcarbonyl, CHR.sup.16 COR.sup.17, CHR.sup.16 P(O)(OR.sup.17).sub.2, P(O)(OR.sup.17).sub.2, CHR.sup.16 P(S)(O)R.sup.17).sub.2, CHR.sup.16 C(O)NR.sup.11 R12, CHR.sup.16 C(O)NH.sub.2, (C.sub.1 -C.sub.4)alkyl substituted with phenoxy or benzyloxy optionally substituted with halogen, (C.sub.1 -C.sub.3)alkyl or (C.sub.1 -C.sub.3)haloalkyl; benzyl optionally substituted with halogen, (C.sub.1 -C.sub.3)alkyl or (C.sub.1 -C.sub.3)haloalkyl; or phenyl optionally substituted with halogen, (C.sub.1 -C.sub.3)alkyl, (C.sub.1 -C.sub.3)haloalkyl Or (C.sub.1 -C.sub.4)alkoxy;
- R.sup.11 and R.sup.13 are independently hydrogen or (C.sub.1 -C.sub.4)alkyl;
- R.sup.12 and R.sup.14 are independently (C.sub.1 -C.sub.4)alkyl, or phenyl optionally substituted with halogen, (C.sub.1 -C.sub.3)alkyl, (C.sub.1 -C.sub.3)haloalkyl or (C.sub.1 -C.sub.4)alkoxy;
- R.sup.11 and R.sup.12 may be taken together as --(CH.sub.2).sub.5 --, or --(CH.sub.2).sub.4 -- in which optionally one or more H-atoms may be replaced by (C.sub.1 -C.sub.3)alkyl, phenyl or benzyl;
- R.sup.13 and R.sup.14 may be taken together with the carbon to which they are attached to form (C.sub.3 -C.sub.8)cycloalkyl;
- R.sup.15 is (C.sub.1 -C.sub.4)alkyl or (C.sub.1 -C.sub.4)haloalkyl;
- R.sup.16 is hydrogen or (C.sub.1 -C.sub.3)alkyl;
- R.sup.17 is (C.sub.1 -C.sub.6)alkyl, (C.sub.3 -C.sub.6)alkenyl or (C.sub.3 -C.sub.6)alkynyl;
- W is 0 or S;
- n is 0, 1 or 2.
- 9. A method of claim 8 wherein the plantation crop is selected from the group consisting of citrus, sugarcane, coffee, banana, oil palm, grapes and rubber.
- 10. A method of claim 8 or 9 employing at least one of the compounds of the group consisting of 4-[4'-chloro-2'-fluoro-5'-(1-methylethoxy)phenyl]-3,5-dioxo-7-fluoro-1,4-diazabicyclo[3.3.0]octane, 4-[4'-chloro-2'-fluoro-5'-(1-methyl-prop-2-ynyloxy)phenyl]-3,5-dioxo-7-fluoro-1,4-diazabicyclo[3.3.0]octane, 4-[4'-chloro-2'-fluoro-5'-(prop-2-ynyloxy)phenyl]-3,5-dioxo-7-fluoro-1,4-diazabicyclo[3.3.0]octane, 4-[4'-chloro-2'-fluoro-5'-(1-methyl-ethoxy)phenyl]-3,5-dioxo-7,7-difluoro-1,4-diazabicyclo[3.3.0]octane, 6-fluoro-2-(7-fluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-tetrahydropyrrolo[1,2-c]imidazole-1,3-dione, 6,6-difluoro-2-(7-fluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-tetrahydropyrrolo[1,2-c]imidazole-1,3-dione (JUPAC), 4-[2-chloro-4-fluoro-5-(6-fluoro-1,3-dioxotetrahydropyrrolo[1,2-c]imidazol-2-yl)phenoxy]but-2-enoic acid methyl ester (JUPAC) and any stereoisomer thereof.
- 11. A method of claim 8 wherein the crop is peanut and the compound is applied preemergence.
Parent Case Info
This application is a Sec. 371 application of PCT application number PCT/EP93/02413, filed 06 Sep. 1993, which is a continuation-in-part of U.S. application Ser. No. 07/942,800, filed 10 Sep. 1992, now abandoned.
PCT Information
Filing Document |
Filing Date |
Country |
Kind |
102e Date |
371c Date |
PCT/EP93/02413 |
9/6/1993 |
|
|
3/10/1995 |
3/10/1995 |
Publishing Document |
Publishing Date |
Country |
Kind |
WO94/05668 |
3/17/1994 |
|
|
US Referenced Citations (2)
Number |
Name |
Date |
Kind |
3948933 |
Fontanella |
Apr 1976 |
|
5482921 |
Seckinger et al. |
Jan 1996 |
|
Continuation in Parts (1)
|
Number |
Date |
Country |
Parent |
942800 |
Sep 1992 |
|