Claims for Patent: 5,605,877

Summary for Patent: 5,605,877

Title:	Bicyclic imides as herbicides
Abstract:	Compounds of Formula I are disclosed which are useful for controlling undesired vegetation ##STR1## wherein Q is ##STR2## and W, R.sup.A.sub.m, R.sup.4 -R.sup.8 are as defined in the disclosure. Also disclosed are compositions containing the compounds of Formula I and a method for controlling undesired vegetation which involves contacting the vegetation or its environment with an effective amount of a compound of Formula I.
Inventor(s):	Schafer; Matthias (Haibach, DE), Drauz; Karlheinz (Freigericht, DE), Feit; Dieter (Wachtersbach, DE), Amuti; Kofi S. (Wilmington, DE)
Assignee:	E. I. Du Pont de Nemours and Company (Wilmington, DE)
Application Number:	08/397,282
Patent 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-d iazobicyclo-[3.3.0]octane, 4-[4'-chloro-2'-fluoro-5'-(1-methyl-prop-2-ynyloxy)phenyl]-3,5-dioxo-7-flu oro-1,4-diazabicyclo[3.3.0]octane, 4-[4'-chloro-2'-fluoro-5'-(2-propynyloxy)phenyl]-3,5-dioxo-7-chloro-1,4-di azabicyclo[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-d iazabicyclo[3.3.0]octane, 4-[4'-chloro-2'-fluoro-5'-(1-methyl-prop-2-ynyloxy)phenyl]-3,5-dioxo-7-flu oro-1,4-diazabicyclo[3.3.0]octane, 4-[4'-chloro-2'-fluoro-5'-(prop-2-ynyloxy)phenyl]-3,5-dioxo-7-fluoro-1,4-d iazabicyclo[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]oxaz in-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.

Details for Patent 5,605,877

Applicant	Tradename	Biologic Ingredient	Dosage Form	BLA	Approval Date	Patent No.	Expiredate
Aimmune Therapeutics, Inc.	PALFORZIA	peanut (arachis hypogaea) allergen powder-dnfp	Powder	125696	January 31, 2020	5,605,877	2015-03-10