BICYCLIC IMIDES AS HERBICIDES

Abstract: Bicyclic imides of formula (I), wherein the bond linking C-7 and C-8 may be single or double; m is 1-7; RA can occupy one or more of the 2 or 6-8 positions and is independently selected from the group: hydroxy, halogen, CN, OR3, (C1-C4)alkyl, S(O)nR3, COR3, C(O)SR3 and C(O)NR11R12; and Q is a phenylic residue substituted with one or more inorganic and/or organic residues which can be substituted, interrupted and/or combined with the aromatic residue with one or more hetero atoms such as N, O or S, preferably at least in the 4' position. These compounds are made from aryl isocyanates of the general formula Q - N = C = O and proline carboxylic acids. The compounds are useful as herbicides.

Description: Bicycl ic Imides as herbicides Description This invention relates to novel bicyclic imides; a method for their preparation; and their use as herbicides . It has already been disclosed that certain heterocyclic imides (see EP-A 272 594, EP-A 493 323, EP-B 0 070 389, EP-B 0 104 532) can be employed as herbicides . Now novel bicyclic imides have been found that exhibit markedly better herbicidal activity with excellent selectivity . The subject of the present invention therefore comprises compounds of formula I wherein the bond linking C-7 and C-θ may be single or double; m is 1 - 7 ; SUBSTITUTE SHEET can occupy one or more of the 2 or 6 - 8 positions and is independently selected from the group: hydroxy, halogen, CN, OR 3 , ( C . -C 4 ) alkyl , S(0) R 3 , COR 3 , C(0)SR 3 and C(0)NR 11 R 12 ; CH Q-2 Q- Q-5 Q-6 Q-7 wherein R 3 is (d-CβJalkyl (C3-C8 )cycloalkyl, (C 3 -C 8 lal enyl , ( C 3 -C 8 ) alkynyl , ( C! -C β ) haloalkyl ( C 2 -Cβ ) alkoxyalkyl , ( C 2 -C 4 ) carboxy alkyl, ( C 3 -C 8 lalkoxycarbonylalkyl, (C 4 -C 8 )alkenyloxyalkyl, (C 4 -C 8 .alkynyloxyalkyl, (C 3 -Cβ Ihaloalkoxyalkyl, (C 3 -C 8 Jtrialkylsilyl, { 3 - C β )cyanoalkyl, (C 3 -C 8 lhaloalkenyl, (C 3 -C β .haloalkynyl, (C 2 -C 8 )alkylcarbonyl, (C 2 -C 8 (alkoxycarbonyl, (C 2 -C 8 )haloalkoxycarbonyl SUBSTITUTE SHEET P(0)(0R 17 ) 2 , CHR 16 P(0) (OR 17 ) 2 or CHR 16 P ( S ) ( OR 17 ) 2 , phenyl or benzyl optionally substituted with halogen, ( C -C 3 ) alkyl , ( C 1 -C 3 ) haloalkyl or ( Cι -C- 4 ) alkoxy ; R 4 is hydrogen or halogen; R 5 is (C 1 -C 2 Jalkyl, ( C . -C 2 ) haloalkyl , 0CH 3 , SCH 3 , 0CHF 2 . halogen, CN or N0 2 ; is hydrogen, ( C 1 -C 8 ) alkyl , ( C 1 -C 8 ) haloalkyl , halogen, OR 10 , S(0) R 10 , COR 10 , C(0)SR 10 , n C(0)NR 11 R 12 , CHO, CH=CHC0 2 R 10 , C0 2 N=CR 13 14 , N0 2 , CN, NHS0 2 R 15 or NHS0 2 NHR 15 ; and R 8 are independently hydrogen, ( Ci -C 3 ) alkyl , ( C 1 -C 3 ) haloalkyl or halogen; when 0 is Q-2 or Q-6, R 7 and R 8 together with the carbon to which they are attached may be C=0; R 9 is ( Ci -C 6 ) alkyl , ( C , -C 6 ) haloalkyl , ( C 2 -C 6 ) alkoxyalkyl , ( C 3 -C 6 ) alkenyl or ( C 3 -C 6 ) alkynyl ; 1 o is (Cι-C β )alkyl, ( C 3 -C β ) cycloalkyl , (C 3 -C 8 ) alkenyl, (C 3 -C 8 )alkynyl , ( C 1 -C 8 ) haloalkyl , (C 2 -C 8 ) alkoxyalkyl, (C 2 -C 6 )alkylthioalkyl, (C 2 -C 8 )alkylsulfinylalkyl, (C 2 -C 8 )alkylsulfonylalkyl, (C 3 -C 8 Jalkoxyalkoxyalkyl, (C 4 -C 8 )cycloalkylalkyl, (C 2 -C 4 )carboxyalkyl, (C 3 -C 8 .alkoxycarbonylalkyl, (Cβ-Cβ )alkenyloxycarbonylalkyl , I C - - C - )alkynyloxycarbonylalkyl, (Cβ-Cβ )cycloalkoxyalkyl, (C 4 -C β )alkenyloxyalkyl, (C 4 -C 8 )alkynyloxyalkyl, (C 3 -C β )haloalkoxyalkyl, (C4-C 8 )haloalkenyloxyalkyl, (C 4 -C B )haloalkynyloxyalkyl, (C 6 -C 8 )cycloalkylthioalkyl, (C 4 -C 8 .alkenylthioalkyl, (C 4 -C β )alkynylthioalkyl, SUBSTITUTE SHEET (C 4 -C 8 Jtrialkylsilylalkyl, (C 3 -C 8 )cyanoalkyl, (C 3 -C 8 )halocycloalkyl, (C 3 -C 8 )haloalkenyl, (Cs-C 8 .alkoxyalkenyl, (Cs-Cg )haloalkoxyalkenyl, (Cs-C 8 )alkylthioalkenyl, (C 3 -C 8 )haloalkynyl, (C 5 -C 8 )alkoxyalkynyl, (Cs-C 8 .haloalkoxyalkynyl, (C 5 -C 8 lalkylthioalkynyl, (C 2 -C 8 )alkylcarbonyl, CHR 16 C0R 17 , CHR 16 P(0) (OR 17 ) 2 , P(0)(0R 17 ) 2 , CHR 16 P(S ) (OR 17 ) 2 , CHR 16 C(0)NR 11 R 12 , CHR 16 C ( 0 )NH 2 , (C 1 -C 4 )alkyl substituted with phenoxy or benzyloxy optionally substituted with halogen, (Cι-C 3 )alkyl or ( Cι -C 3 ) haloalkyl ; benzyl optionally substituted with halogen, (C 1 -C 3 ) alkyl or (Cι-C 3 ) haloalkyl; or phenyl and pyridyl optionally substituted with halogen, ( C 1 -C 3 ) alkyl , ( C 1 -C 3 )haloalkyl or ( C1 -C4 ) alkox ; R 11 and R 13 are independently hydrogen or (C1-C4.alkyl; R 12 and R 4 are independently ( C 1 -C 4 ) alkyl , or phenyl optionally substituted with halogen, ( C 1 -C3 ) alkyl , ( C 1 -C 3 ) haloalkyl or ( C , -C 4 ) alkoxy ; R 11 and R 12 may be taken together as -(CH 2 ) 5 -, -(CH 2 _4- or -CH 2 CH 2 OCH 2 CH 2 - , in which optionally one or more H-atoms may be replaced by ( Ci -C3 ) alkyl , phenyl or benzyl; R 13 and R 14 may be taken together with the carbon to which they are attached to form (C 3 -C 8 .cycloalkyl; R 15 is (Cι-C 4 )alkyl or ( C 1 -C 4 ) haloalkyl ; R 16 is hydrogen or ( C 1 -C 3 ) alkyl ; R 17 is ( Ci -C 6 .alkyl, ( C 3 -C 6 )alkenyl or ( C 3 -C 6 ) alkynyl; W is 0 or S ; π is 0 , 1 or 2 ; provided that SUBSTITUTE SHEET 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 A bond, then at least one R is other than hydroxy, halogen, (C-|-C 4 )alkyl and ( C 1 -C 4 ) alkoxy . The subject of the present invention comprises further bicyclic imides selected from the group consisting of 4-[4'-chloro-2 / -fluoro-5'-{prop-2-ynyloκy)phenyl]-3,5- dioxo-7-fluoro- 1 , 4-diazabicyclo-C3.3.0]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-methyl-ethoxy)phenyl]-3,5-dioxo-7,7-difluoro- 1 , 4-diazabicycloC3.3.0]octane and stereoisomers thereo . In the above definitions, the term "alkyl" , used either alone or in compound words such as "alkylthio" or "haloalkyl" , includes straight chain or branched alkyl, e. g. , methyl, ethyl, n-propyl, isopropyl or the different butyl isomers. Alkoxy includes e. g. methoxy, ethoxy, n-propyloxy, isopropyloxy and the different butoxy isomers. Alkenyl includes straight chain or branched alkenes, e. g. , 1-propenyl, 2-propenyl, 3-propenyl and the different butenyl isomers. Cycloalkyl includes e. g. cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. The term "halogen" , either alone or in compound words such as "haloalkyl", means fluorine, chlorine, bromine or iodine. Further, when used in compound words such as "haloalkyl" said alkyl may be partially or fully substituted with halogen atoms, which may be the same or different. Examples of haloalkyl include CH CH F, CF 2 F 3 and CH CHFC1. More preferred are compounds of formula I having at least one of the following specifications R 3 is preferred (C -C. )al yl, (C -C )cycloalkyl, .C -C„ .alkenyl, ( C -C_ ) alkynyl , ( C - C . ) haloalkyl , j D j fa 1 4 (C.-C, ) alkoxyalkyl , (C -C. ) carboxyalkyl , 2 4 4 ( -C_ ) alkoxycarbonylalkyl , J b (C, -C_)alkenyloxyalkyl, (C.-C.) alkynyloxyalkyl, 4 b 4 b ( C j-C_b)haloalkoκyalkyl, (CJ,-C_b)trιalkylsιlyl, ( C -C_ . cyanoalkyl, (C--C r ]haloalkenyl, j b j b ( C- -C_ ) haloalkynyl , (C -C_)alkyl carbonyl, 6 17 2 6 P(0) (0R )„ , ( C -C e ) alkoxycarbonyl, 1 B 17 ( -C_ lhaloalkoxycarbonyl , CHR P(0) (0 ) „ or 16 1 CHR P .SMOR ) phenyl or benzyl optionally substituted with halogen, (C -C_ )alkyl, ( C -C_ ) haloalkyl or (C.-C, lalkoxy; I J 1 4 R s halogen or CN; R 6 is hydro halogen, , C(0)NR 1 1 or NHSO 7 8 R and R are independently hydrogen, (C -C_)alkyl or 7 8 ( C -C_ ) haloalkyl ; when Q is Q-2 or Q-6, R and R together with the carbon to which they are attached may be C=0; R 9 is ( C -C. Jalkyl, ( C - C. ) haloalkyl , 1 4 1 4 ( C.-C. ) alkoxyalkyl , ( C -C_) alkenyl or 4 J b (C 3 -C 6 .alkynyl; SUBSTITUTE SHEET ,10 is ( C 1 -c Jalkyl, ( C 3 -C 8 ) cycloalkyl , (C 3 -C 6 )alkenyl, ( C 3 ~C β ) alkynyl , ( C 1 -C 4 ) haloalkyl , (C__.-C4, )alkoxyalkyl , (C__:-C4, ) alkylthioalkyl , (C__;-C4, ) alkylsulfinylalkyl , ( C 2 -C ) alkylsulfonylalkyl, <C -C_ )alkoxyalkoxyalkyl, (C,-C β )cycloalkylalkyl, (C.-C, ) carboxyalkyl , ( C -C_ ) alkoxycarbonylalkyl , . 4 J b (Cb-Co )alkenyloxycarbonylalkyl, ( C -C R Jalkynyloxycarbonylalkyl, (C -C )cycloalkoxyalkyl, . C ^ - C & Jalkenyloxyalkyl, alkynyloxyalkyl, (C_-Cg)haloalkoxyalkyl, ( C -C )haloalkenyloxyalkyl, ( C -C_ )haloalkynyloxyalkyl, ( C -C. Jcycloalkylthioalkyl, ( -C ) alkenylthioalkyl, (C.-C )alkynylthioalkyl, (C -Cgltrialkylsilylalkyl, ( C_-C 4 ) cyanoalkyl, ( C 3 -Cg)halocycloalkyl, (C 3 -Cg)haloalkenyl, ( C -Cg)alkoxyalkenyl, (C_-C_)haloalkoxyalkenyl, ( C-.-Cg)alkylthioalkenyl, (C_-Cg)haloalkynyl, (C -C )alkoxyalkynyl, (C c -C c )haloalkoxyalkynyl, ( C -Cg ) alkylthioalkynyl , (C 2 ~C 4 )alkyl carbonyl, CHR 16 C0R 17 CHR 16 P(0) (OR 17 ) P(0) (OR 17 ) , CHR 16 P(S) (OR 17 ) CHR 16 C(0)NR 11 R 12 CHR C(0)NH, 2 ά (C -C„)alkyl substituted with phenoxy or benzyloxy optionally substituted with halogen, (C -C_)alkyl or ( C -C 3 )haloalkyl ; benzyl optionally substituted with halogen, (C..-C Jalkyl or ( C 1 -C 2 ) haloalkyl ; or phenyl and pyridyl optionally substituted with halogen, ( C .. -C 3 ) alkyl , ( C 1 -C 3 ) haloalkyl or (C -C, )alkoxy; ,12 and R are independently (C -C.Jalkyl, phenyl optionally substituted with halogen, (C -C Jalkyl, (C 1 -C 2 Jhaloalkyl or ( C 1 -C ? ) alkoxy ; SUBSTITUTE SHEET R11 and R12 may be taken together as -(CH„) -, 2 5 -( H 2 ) 4 - or -CH 2 H 2 0CH 2 CH 2 - , each ring optionally substituted with ( C.. _ c ) alkyl , phenyl or benzyl; 13 14 R and R may be taken together with the carbon to which they are attached to form ( C -C_ ) cycloalkyl ; ,17 is ( C 1 -C 4 Jalkyl , (C 3 -C g ) alkenyl or ( C 3 ~Cg )alkynyl Compounds having a substituted proline residue, particularly in 7-position, exibit a beneficial effect on undesired plants, preferred are fluoro, bromo or chloro . Particularly preferred method of use employs compounds of formula II in which R is hydrogen, halogen, (C -C Jalkyl, OR 3 , S(0) R 3 n COR 3 , CO R 3 C(0)SR 3 C(0)NR 11 R 12 or CN; R 2 is halogen, (C 1-C, Jalkyl, OR 3 , S(0) nR 3 , COR 3 C0 2 R 3 C(0)SR 3 C(0)NR 11 R 12 or CN . Especially preferred method of use employs compounds of formula II in which at least one of R 1 - R3 has the meaning SUBSTITUTE SHEET = hydrogen or ( C ■ C 4 )alkyl; = fluoro, chlαro, bromo, OR 3 , S(0) R3 , CO R 3 , C(0)NR 1 ' R 12 or C ; = (C..-C Jalkyl, ( C 3 -Cg ) cycloalkyl , ( C 3 ~C g )alkenyl (C -Cg)alkynyl, ( C 1 -C ) haloalkyl or (C -C c Jtrialkylsilyl. J b Most preferred method of use employs compounds of formula II with at least one of the following specifications = hydrogen , 3 = fluoro, chloro, bromo or OR , = (C -C 2 )alkyl, ( C, -C 2 ) haloalkyl and in Q ^ 4 is fluoro or chloro; is chloro; is OR,10 C0 2 R 10 NHS0 2 R 10 or SR 10 is hydrogen; is hydrogen or methyl; is ( C 3 -C 4 ) alkenyl or ( C 3 ~C 4 ) alkynyl ; ,10 is ( C 1 -C ) alkyl , ( C -Cg ) cycloalkyl , (C -CgJalkenyl. (C 3 ~C 4 ) alkynyl , ( C -C 3 )haloalkyl ( C -C ) alkoxyalkyl , ( C_-C_ ) alkoxycarbonylalkyl , 6 8 (C -C ) alkenyloxycarbonylalkyl , 6 8 (C -C ) alkynyloxycarbonylalkyl or (C 1 -C2 ) carboxyalkyl . If not otherwise specified the invention relates to both the individual possible stereoisomers of formula SUBSTITUTE SHEET I and II and also mixtures of the isomers. Stereoisomers exhibiting the 2R-configuration are preferred to others. The 2R-configuration exhibits significantly bette control, e. g. up to 8-fold, compared with the 2S-configuration on undes red plants. Subject of the invention is also a method for preparing the novel bicyclic imides comprising: (a) reacting a compound of formula III Q—NCO III with a compound of formula IV IV wherein R=H or ( C . - C ) alkyl , and cyclizing the intermediate and a method for preparing bicyclic imides of formula la I . SUBSTITUTE SHEET wherein the bond linking C-7 and C-8 may be single or double ; is 1 - 7 ; A R can occupy one or more of the 2 or 6 - 8 positions and is independently selected from the group; hydroxy, halogen, CN, OR 3 , ( C . -C 4 )alkyl , S(0) R 3 , COR 3 , C(0)SR 3 and C(0)NR 11 R 12 Q-I Q-2 -3 Q- 4 Q-5 Q-6 Q-7 wherein R 3 is (CT-Cβ Jalkyl, ( C 3 -C 8 ) cycloalkyl , ( C 3 -C 8 Jalkenyl, ( C 3 -C 8 ) alkynyl , ( C, -C β ) haloalkyl , ( C 2 -C 8 ) alkoxyalkyl , ( C 2 -C 4 ) carboxy alkyl, (C 3 -C 8 Jalkoxycarbonylalkyl, ( C 4 -C β Jalkenyloxyalkyl, (C 4 -C 8 ) alkynyloxyalkyl, SUBSTITUTE SHEET (C 3 -C 8 Jhaloalkoκyalkyl, (C 3 -C 8 Jtrialkylsilyl, (C 3 -C 8 lcyanoalkyl, (C 3 -C 8 )haloalkenyl, (C 3 -C β )haloalkynyl, (C 2 -C 8 lalkylcarbonyl, (C 2 -C 8 )alkoxycarbonyl, ( C 2 ~ β l aloalkoxycarbonyl, P(0) (0R 17 ) 2 , CHR 16 P(0) (OR 17 ) 2 or CHR 6 P ( S ) ( OR 17 ) 2 , phenyl or benzyl optionally substituted with halogen, ( C 1 -C 3 ) alkyl , ( C 1 -C 3 ) haloalkyl or (Cι-C 4 )alkoκy; R 4 is hydrogen or halogen; R 5 is (d-C 2 Jalkyl, ( C . -C 2 ) haloalkyl , 0CH 3 , SCH 3 , 0CHF 2 , halogen, CN or N0 2 ; is hydrogen, ( C 1 -C 8 ) alkyl , ( C 1 -C 8 ) aloalkyl , halogen, OR 10 , C 0R 10 , C(0)SR 10 , C(0)NR 1 1 R 12 , CHO, CH=CHC0 2 R 10 , CO 2 =C 13 R 14 , N0 2 , CN, NHS0 2 R 15 or NHS0 2 NHR 15 ; and R e are independently hydrogen, (C 1 -C 3 Jalkyl, (Cι-C 3 )haloalkyl or halogen; when Q is Q-2 or Q-6, R 7 and R 8 together with the carbon to which they are attached may be C=0 ; is ( C 1 -C 6 ) alkyl , ( C 1 -C 6 ) haloalkyl , ( 2 - C ) alkoxyalkyl , ( C 3 -C 6 ) alkenyl or ( C 3 -Cβ ) alkynyl ; 1 o is ( Ci -C 8 ) alkyl , ( C 3 -C 8 ) cycloalkyl , (C 3 -C 8 Jalkenyl , ( C 3 -C 8 ) alkynyl , ( , -C 8 ) haloalkyl , (C 2 -C 8 ) alkoxyalkyl, (C 2 -C 6 ) alkylthioalkyl, (C 2 -C 8 ) alkylsulfinylalkyl, (C 2 -C 8 Jalkylsulfonylalkyl, (C 3 -C 8 Jalkoxyalkoxyalkyl, (C 4 -C 8 Jcycloalkylalkyl, ( C 2 -C 4 Jcarboxyalkyl, (C 3 -C 8 )alkoxycarbonylalkyl, (C6-C 8 Jalkenyloxycarbonylalkyl, { C 6 - C β ) alkynyloxycarbonylalkyl , (C 6 ~C 8 Jcycloalkoxyalkyl, (C 4 -C 8 Jalkenyloxyalkyl, (C 4 -C 8 Jalkynyloxyalkyl, (C 3 -C 8 Jhaloalkoxyalkyl, (C 4 -C 8 Jhaloalkenyloκyalk l, (C 4 -C 8 Jhaloalkynyloxyalkyl, ( C6-C 8 Jcycloalkylthioalkyl, (C 4 -C 8 Jalkenylthioalkyl, (C -C 8 Jalkynylthioalkyl, (C 4 -C 8 Jtrialkylsilylalkyl, (C 3 -C 8 ) cyanoalkyl, (C 3 -C 8 Jhalocycloalkyl, (C 3 -C 8 Jhaloalkenyl, (Cs-C 8 Jalkoxyalkenyl, (C 5 -C 8 Jhaloalkoxyalkenyl, (C 5 -C 8 Jalkylthioalkenyl, (C 3 -C β Jhaloalkynyl, ( C 5 -C 8 Jalkoxyalkynyl, ( C 5 -C 8 Jhaloalkoxyalkynyl, (Cs-C 8 Jalkylthioalkynyl, (C 2 -C 8 Jalkylcarbonyl, CHR 16 C0R 17 , CHR 16 P(0) (OR 17 ) 2 , P(0)(0R 17 ) 2 , CHR 16 P(S) (OR 17 ) 2 , CHR 16 C(0)NR 11 R 12 , CHR 16 C ( 0 ) H 2 , (Cι-C )alkyl substituted with phenoxy or benzyloxy optionally substituted with halogen, (Cι-C 3 )alkyl or ( Cι -C 3 ) haloalkyl; benzyl optionally substituted with halogen, (Cι-C 3 )alkyl or ( C . -C 3 )haloalkyl; or phenyl and pyridyl optionally substituted with halogen, ( C 1 -C 3 ) alkyl , ( C . -C 3 ) haloalkyl or ( Cι -C 4 ) alkoxy ; R 11 and R 13 are independently hydrogen or ( C 1 -C 4 Jalkyl ; R 12 and R 14 are independently ( C 1 -C 4 )alkyl , or phenyl optionally substituted with halogen, (C1-C3 Jalkyl, ( C 1 -C 3 ) haloalkyl or (C 1 -C 4 )alkoxy; R 11 and R 12 may be taken together as -(CH 2 ) 5 -, -(CH 2 ) 4 - or -CH 2 CH 2 0CH 2 CH 2 - , in which optionally one or more H-atoms may be replaced by ( Ci-C 3 ) alkyl , phenyl or benzyl; R 13 and R 14 may be taken together with the carbon to which they are attached to form (C 3 -C 8 ) cycloalkyl; R 15 is (Cι-C 4 )alkyl or ( , - C 4 ) aloalkyl ; R 16 is hydrogen or ( C 1 -C 3 ) alkyl ; SUBSTITUTE SHEET R 17 is ( C ι -C 6 ) alkyl , ( C 3 -C 6 ) alkenyl or ( C 3 -C 6 J alkynyl ; W is 0 or S ; n is 0 , 1 or 2 ; selected from the group consisting of (b) or (c): (b) reacting a compound of formula IV, wherein R=H or ( C ι -C 4 ) alkyl , with phosgene and then with an amine of formula VI Q—NH 2 VI to form compounds of formula VII, and cyclizing the compounds of formula VII, or (c) reacting a compound of formula III with a compound of formula VIII VIII to form a compound of formula I K SUBSTITUTE SHEET and hydrolyzing and cylizing the compound of formula IX. The novel bicyclic imides can be produced in a method comprising preparing a compound of formula II wherein is R' is and H comprising reacting a compound of formula X, X wherein R=H or ( C 1 -C 4 )alkyl , with a compound of general formula III, Q—NCO III and converting the reaction product formed thereby SUBSTITUTE SHEET Subject of the invention is further a method for making compounds of formula la i wherein the bond linking C-7 and C-8 may be single or double ; m is 1 - 7 ; R A can occupy one or more of the 2 or 6 - 8 positions and is independently selected from the group: hydroxy, halogen, C , OR 3 , ( C 1 -C 4 )alkyl , S(0) R3 _ COR 3 , C(0)SR 3 and C(0)NR 1 1 R 12 ; is Q-l Q-2 Q-3 SUBSTITUTE SHEET Q-5 Q-6 -7 wherein R 3 is ( d -C 8 Jalkyl , ( C 3 -C 8 ) cycloalkyl , ( C 3 -C 8 ) alkenyl , ( C 3 - 8 ) alkynyl , ( C -C 8 ) haloalkyl , ( C 2 -C 8 ) alkoxyalkyl , ( C 2 -d ) carboxy alkyl, (C 3 -C 8 )alkoxycarbonylalkyl, (d-C 8 Jalkenyloxyalkyl. (C 4 -C 8 ) alkynyloxyalkyl, (C 3 -C 8 )haloalkoxyalkyl, (C 3 -C 8 )trialkylsilyl, (C 3 -C 8 Jcyanoalkyl, (C 3 -C 8 Jhaloalkenyl, (C 3 -C β Jhaloalkynyl, (C 2 -C β Jalkylcarbonyl, (C 2 -C B Jalkoxycarbonyl, (C 2 -C β lhaloalkoxycarbonyl, P(0) (OR 17 ) 2 , CHR 16 P (0 ) ( OR 17 ) 2 or CH 16 P( S ) (OR 17 ) 2 phenyl or benzyl optionally substituted with halogen, ( C 1 -C 3 ) alkyl , ( C . -C 3 ) haloalkyl or ( Cι -C 4 J alkoxy ; SUBSTITUTE SHEET is hydrogen or halogen; R 5 is ( Ci -C 2 Jalkyl , ( d -C 2 ) haloalkyl , 0CH 3 , SCH 3 , 0CHF 2 , halogen, CN or N0 2 ; R 6 is OR 10 , S(0) R 10 , NHS0 2 R 15 or NHS0 2 NHR 15 ; n R 7 and R θ are independently hydrogen, ( Ci -C 3 ) alkyl , ( C 1 -C 3 ) aloalkyl or halogen; when Q is Q-2 or Q-6, R 7 and R 8 together with the carbon to which they are attached may be C=0 ; R 9 is ( Cι - 6 ) alkyl , ( C 1 - 6 ) haloalkyl , ( C 2 -C 6 ) alkoxyalkyl , ( C 3 -C 6 ) alkenyl or ( C 3 -C 6 ) alkynyl ; 1 o is ( C ι -C β ) alkyl , ( C 3 -C 8 ) cycloalkyl , ( C 3 -C 8 ) alkenyl , ( C 3 -C 8 ) alkynyl , ( d -C 8 ) haloalkyl , (C 2 -C 8 ) alkoxyalkyl, I C 2 - C 6 Jalkylthioalkyl, (C 2 -C 8 Jalkylsulfinylalkyl, (C 2 -C 8 Jalkylsulfonylalkyl, (C 3 -C 8 Jalkoxyalkoxyalkyl, (C 4 -C 8 Jcycloalkylalkyl, (C 2 -C 4 Jcarboxyalkyl, (C 3 -C 8 Jalkoxycarbonylalkyl, (Cβ- a Jalkenyloxycarbonylalkyl, (Cβ-Cβ ) alkynyloκycarbonylalkyl , (C 6 -C 8 Jcycloalkoxyalkyl, (C 4 -C β Jalkenyloxyalkyl, (C 4 -C 8 ) alkynyloxyalkyl, (C 3 -C 8 Jhaloalkoxyalkyl, ( -C 8 J aloalkenyloxyalkyl, (C 4 -C 8 Jhaloalkynyloxyalkyl, (C 6 -C 8 Jcycloalkylthioalkyl, (C 4 -C 8 Jalkenylthioalkyl, (C 4 -C 8 Jalkynylthioalkyl, (C 4 -C 8 Jtrialkylsilylalkyl, (C 3 -C 8 ) cyanoalkyl, (C 3 -C 8 Jhalocycloalkyl, { C 3 - C 8 Jhaloalkenyl, (C 3 -C 8 Jalkoxyalkenyl, (Cs-C 8 Jhaloalkoxyalkenyl, (C 5 -C 8 Jalkylthioalkenyl, (C 3 -C 8 Jhaloalkynyl, ( C 5 -C 8 Jalkoxyalkynyl, (C 5 -C 8 Jhaloalkoxyalkynyl, [ C 5 - C β Jalkylthioalkynyl, (C 2 -C 8 Jalkylcarbonyl, CHR 16 C0R 17 , CHR 16 P(0) (OR 17 ) 2. P(0) (OR 17 ) 2 , SUBSTITUTE SHEET CHR 16 P ( S ) (OR 17 ) 2 , CHR 6 C(0)NR 1 1 R 12 , CHR 16 C ( 0 ) H 2 , (Cι-C 4 )alkyl substituted with phenoxy or benzyloxy optionally substituted with halogen, (Cι-C 3 )alkyl or ( C ι -C 3 ) haloalkyl ; benzyl optionally substituted with halogen, (C 1 -C 3 Jalkyl or (Cι-C 3 )haloalkyl; or phetlyl and pyridyl optionally substituted with halogen, ( C . -C 3 ) alkyl , ( C , -C 3 ) haloalkyl or (C 1 -C lalkoκ ; R 1 1 and R 13 are independently hydrogen or ( d -C ) alkyl ; R 2 and R 14 are independently ( C 1 -C 4 ) alkyl , or phenyl optionally substituted with halogen, (d-C 3 )alkyl, ( C , - C 3 ) haloalkyl or ( C . -C 4 ) alkoxy ; R 1 1 and R 1 2 may be taken together as -(CH 2 )s-, -(CH 2 ) 4 - or -CH 2 CH 2 OCH 2 CH 2 - , in which optionally one or more H-atoms may be replaced by ( C 1 -C 3 ) alkyl , phenyl or benzyl; R 13 and R 14 may be taken together with the carbon to which they are attached to form (C 3 -C 8 Jcycloalkyl; R 15 is (d-C 4 )alkyl or ( C , -C 4 ) haloalkyl ; R 16 is hydrogen or ( , -C 3 ) alkyl ; R 17 s ( d -C 6 ) alkyl , ( C 3 -C 6 ! alkenyl or ( C 3 -C 6 ) alkynyl ; W is 0 or S ; n is 0 , 1 or 2 ; comprising reacting a compound of the formula XIII SUBSTITUTE SHEET wherein Y = 0, S, NH with a halide selected from the group 10. R 15 S0 2 -Z and 15 NHSO' wherein Z is chlorine, bromine or iodine. The novel bicyclic imides of general formula I are obtained in accordance with the invention by a general method A if arylisocyanates of general formula III Q - N = C = " 0 III in which R to R have the meanings indicated above and proline carboxyl c acids (esters) of general formula IV m * f NH CCbR IV in which m and R have the meaning indicated above and R = H or ( C. -C, Jalkyl or active ester such as 0-succ mιd esters or anhydride esters are reacted in accordance with method A, optionally in the presence of an acid acceptor and optionally in the presence o a solvent . SUBSTITUTE SHEET A further sub 3 ect of the invention is a method B for the prepa ation of compounds of formula I, which is A outlined in what follows and m and R have the meanings indicated above. Therefor a compound of formula IV, wherein R = H or (C -C Jalkyl, is reacted 1 4 with phosgene or a phosgene substitute Ce. g. , tπphσsgene ( CC1 3 0 ) 2 C=0] , first to compounds of formula V. Compounds of formula V are then reacted with compounds of formula VI to form compounds of formula VII. Subsequent cyclization forms compounds of formula I . A further subject of the invention is method C for the preparation of compounds of formula I, which is outlined n what follows and m and R have the meanings indicated above, where a compound of formula III is reacted with a compound of formula VIII, optionall in the presence of an acid acceptor and optionally in the presence of a solvent, to a compound SUBSTITUTE SHEET of formula IX, and the compound IX so obtained is then hydrolysed and cyclized to compounds of formula I. IX A further subject of the invention is method D for the preparation of compounds of formula II, which is outlined in what follows and R anc j R^ have the meaning indicated above. Therefor a compound of general formula X, wherein R = H or (C , 1-C4, Jalky " l ' is reacted with a compound of general formula III, yielding a compound of general formula XI. Compounds of general formula XI are cyclized to compounds of general formula XII and converted to compounds of ormula I I . SUBSTITUTE SHEET HO O^R XI A further subject of the invention is a method E for the preparation of compounds of formula I by reacting compounds of general formula XIII SUBSTITUTE SHEET wherein m, RA , R4 and R5 have the meaning indicated above and Y = 0, S, NH with a halide of the formula XIV , XV or XVI , 10 - z R 15 S0. 15 NHS0, XIV XV XVI wherein Z is a chlorine-, bromine - or an iodine atom and R and R have the meanings indicated above. In method A, the reaction for R = alkyl takes place in an inert organic solvent, for example in an aromatic solvent such as toluene, chlorobenzeπe , a halogenated hydrocarbon such as chloroform, methylene chloride, an ether such as dnsopropyl ether, or in acetonitrile or dimethylformamide , optionally with base catalysis preferred at temperatures of 20 to 120°C. Preferably used as bases are organic bases, for example organic amines such as tπethylamine or also pyπdine (see EP-A 0 272 594 ) . For R = H, the reaction takes place in water as solvent or, preferably, in the two-phase system water organic solvent. Especially preferred is the mode of operation in which compounds of formula IV, optionally salts of IV, is added together in water with an inorganic base, for example an alkali or alkaline- earth metal hydroxide, carbonate or hydrogen carbonate, such as sodium hydroxide or also potassium carbonate, or an organic base, for example an organic amine such as tπethyla ine , and then compounds of formula III, dissolved in an inert solvent such as, SUBSTITUTE SHEET for example toluene, chlorobenzene or chloroform is added. The reaction mixture is then held o ad antageously at temperatures between -40 C to + 120°C, pre erably - 10° to +40°C, up to several days, preferably between 3 and 50 h. The aqueous phase is then adjusted to a pH value between 1 and 3 with acid, preferably with an inorganic acid such as aqueous hydrochloric acid or aqueous sulfuπc acid. The ureas of formula VII thus formed are then cyclized at temperatures between 50 and 100°C or, optionally, n the presence of an acid such as hydrochloric acid and/or hydroformic acid or, optionally by conversion to an ester (R = alkyl) by know methods (see Houben-Weyl, "Methoden der organischen Chemie" CMethods of Organic Chemistry] , Vol. XV ( 1974 ) ) . In method D, the reaction for R = H and (C -C. Jalkyl 1 4 takes place analogous to method A to give compounds of formula XII. Known methods (see Houben-Weyl, "Methoden der organischen Chemie" CMethods of Organic Chemistry] Vol. EP-B 0 078 191 ) and standard chemistry (see Advanced Organic Chemistry, Jerry March, second edition 1977) leads to compounds of formula II. The compounds of formula III are known or can be prepared by analogy with known methods; see Houben-Weyl, "Methoden der organischen Chemie" CMethods of Organic Chemistry] , Vol. VIII , p. 120 ( 1952) , Houben-Weyl, Vol. IX, pp. 875, 869 ( 1955) ; EP-B 0 070 389; US-A 4 881 967; EP-A 0 322 401 ; US-A 3 495 967; EP-A 0 300 307; EP-A 0 349 832. SUBSTITUTE SHEET Compounds of general formula IV or X are commercially available or prepared according to methods described in the literature (e. g. S. Kaπenasa et al. , J. Org. Chem. 58 , 2875 ( 1991 ) , P Beaulien et al. , J. Chem. Soc. Perkin. Trans. I 11 , 2885 ( 1991 ) ; R.M. Kellog et al. , Tetrahedron Lett. 32(30) , 3727 ( 1991 ) and many more) , Houben-Weyl, Vol. XXV/1 and XXV/2 ( 1974 ) . The latter literature describes also the active esters. Amines of general formula VIII are known or can be prepared in accordance with EP-A 0 073 569 or in an analogous fashion in accordance with the method described there. The 2R-configuration can be achieved starting from the corresponding optically active proline or proline derivatives analogous to the methods specified above. Finally, it was found that the bicyclic imides of general formula I and II exhibit outstanding herbi idal qualities. A further subject of the invention is a composition for controlling weeds comprising an effective amount of at least one of the novel bicyclic imides and at least one carrier therefor. A further subject of the invention is a method for controlling weeds comprising applying to the locus to be protected an effective amount of at least one of the novel bicyclic imides. SUBSTITUTE SHEET A further subject of the invention is a method for controlling weeds in plantation crops and peanut comprising applying to the locus to be protected an effective amount of a compound of formula la: I CL wherein the bond linking C-7 and C-8 may be single or double ; is 1 - 7 ; R can occupy one or more of the 2 or 6-8 positions and is independently selected from the group: hydroxy, halogen, CN , OR 3 , ( C 1 -C 4 ) alkyl , S(0) R3 n ' Q-5 Q r_ τ SUBSTITUTE SHEET wherein R 3 s ( d -C 8 Jalkyl , ( C 3 -C β ) cycloalkyl , ( 3 -C 8 ) alkenyl , ( C 3 -C β ) alkynyl , ( ,-C 8 ) haloalkyl , (C 2 -C 8 Jalkoxyalkyl, (C 2 -C 4 )carboxy alkyl, (d-Ca Jalkoxycarbonylalkyl, (C 4 -C 8 Jalkenyloxyalkyl, (C 4 -C 8 ) alkynyloxyalkyl, (C 3 -C 8 Jhaloalkoxyalkyl, (C 3 -C 8 Jtπalkylsilyl, (C 3 -C 8 ) cyanoalkyl, { C 3 - C B Jhaloalkenyl, (C 3 -Cβ Jhaloalkynyl, ( 2 -C 8 Jalkylcarbonyl, (C 2 -C 8 Jalkoxycarbonyl, (C 2 -C 8 Jhaloalkoxycarbonyl, P(0) (OR 17 ) 2 , CHR 16 P (0 ) (OR 17 ) 2 or CHR 16 P ( S ) (OR 17 ) 2 phenyl or benzyl optionally substituted with halogen, (Cι-C 3 )alkyl, (C 1 -C 3 )haloalkyl or ( C1 -C_t ) alkoxy; R 4 is hydrogen or halogen; R 5 is ( d -C 2 Jalkyl , ( C 1 -C 2 ) haloalkyl , 0CH 3 , SCH 3 , 0CHF , halogen, CN or N0 2 ; is hydrogen, ( C1 -C 8 ) alkyl , ( C, -C 8 ) haloalkyl , halogen, OR 10 , S(0)nR 10 , COR 10 , C(0)SR 10 , C(0)NR 11 R 12 , CHO, CH=CHC0 2 R 10 , CO 2 N=CR 13 R 14 , N0 2 . CN, NHS0 2 R 15 or NHS0 2 NHR 15 ; and R β are independently hydrogen, ( C 1 -C 3 ) alkyl , ( C , -C3 ) haloalkyl or halogen; when Q is Q-2 or Q-6, R 7 and R 8 together with the carbon to which they are attached may be C=0; R β is ( d -C 6 Jalkyl, ( C , -C 6 ) haloalkyl , ( C 2 -Ce ) alkoxyalkyl , ( C 3 -C 6 ) alkenyl or ( C 3 -Cβ ) alkynyl ; 10 is ( C 1 -C 8 ) alkyl , ( C 3 -C 8 ) cycloalkyl , (C 3 -C β Jalkenyl, ( C 3 -C 8 ) alkynyl , ( C , -C 8 ) haloalkyl , (C -C 8 ) alkoxyalkyl, (C 2 -C 6 Jalkylthioalkyl, (C 2 -C 8 lalkylsulfiπylalkyl, (C 2 -C 8 lalkylsulfonylalkyl, SUBSTITUTE SHEET (C 3 -C 8 Jalkoxyalkoxyalkyl, ( C 4 -C 8 Jcycloalkylalkyl, (C 2 -C 4 lcarboxyalkyl, (C 3 -C 8 Jalkoxycarbonylalkyl, (C 6 -C 8 ) alkeπyloxycarbonylalkyl , ( C 6 -C 8 ) alkynyloxycarbonylalkyl , (C 6 -C 8 Jcycloalkoxyalkyl, ( C 4 - C β lalkenyloxyalkyl, (C 4 -C 8 ) alkynyloxyalkyl, (C 3 -C 8 ihaloalkoxyalkyl, (C -C 8 Jhaloalkenyloxyalkyl, (C 4 -C 8 Jhaloalkynyloxyalkyl, (C 6 -C 8 Jcycloalkylthioalkyl, (C 4 -C 8 Jalkenylthioalkyl, (C 4 -C 8 Jalkyπylthioalkyl, (C 4 -C 8 )trιalkylsilylalkyl, (C 3 -C 8 ) cyanoalkyl, (C 3 -C 8 Ihalocycloalkyl, (C 3 -C 8 lhaloalkenyl, ( C 5 -C 8 Jalkoxyalkenyl, ( C 5 -C 8 Jhaloalkoxyalkenyl, (C 5 -C 8 Jalkylthioalkenyl, (C 3 -C θ Jhaloalkynyl, ( C 5 -C 8 )alkoxyalkynyl, (Cs-C 8 Jhaloalkoxyalkynyl, (Cs-C 8 Jalkylthioalkynyl, (C ∑ -C 8 Jalkylcarbonyl, CHR 16 C0R 17 , CHR 16 P(0) (OR 17 ) 2 , P(0) (0R 17 ) 2 . CHR 16 P ( S ) (OR 17 ) 2 , CHR 16 C (OJNR 11 R 1 - , CHR 16 C ( 0 ) NH2 , (C 1 -C 4 )alkyl substituted with phenoxy or benzyloxy optionally substituted with halogen, (d-C 3 )alkyl or ( C 1 -C 3 ) haloalkyl ; benzyl optionally substituted with halogen, (C 1 -C 3 )alkyl or ( C 1 -C 3 ) haloalkyl ; or phenyl and pyridyl optionally substituted with halogen, ( C 1 -C 3 ) alkyl , ( C 1 -C 3 ) haloalkyl or ( C 1 -C4 ) alkoxy ; R 1 1 and R 13 are independently hydrogen or ( d-C 4 Jalkyl; R 12 and R 14 are independently ( C , -C 4 ) alkyl , or phenyl optionally substituted with halogen, ( Ci -C 3 ) alkyl , ( C 1 -C 3 ) haloalkyl or ( -C 4 ) alkoxy ; R 1 1 and R 12 may be taken together as -(CH ∑ Js-, -(CH 2 >4- or -CH 2 CH 2 0CH 2 CH 2 - , in which optionally one or more H-atoms may be replaced by ( C 1 -C 3 ) alkyl , phenyl or benzyl; SUBSTITUTE SHEET R 13 and R 14 may be taken together with the carbon to which they are attached to form (C 3 -C 8 ) cycloalkyl; R 15 is (Ci-d Jalkyl or ( C , - C 4 ) haloalkyl ; R 16 is hydrogen or ( C 1 -C 3 ) alkyl ; R 17 is (d-Ce)alkyl; ( C 3 -C 6 ) alkenyl or ( C 3 -C 6 ) alkynyl W is 0 or S ; n 1s 0 , 1 , or 2. In this method is preferred the plantation crop selected from the group consisting of citrus, sugarcane, coffee, banana , oil palm, grapes and rubber. Further is preferred employing at least one of the compounds of the group consisting of 4- 4 ' -chloro- 2' -fluoro-5' - ( 1-methylethoxy)phenyl]-3 , 5-dιoxo-7- fluoro-1 ,4-dιazabιcycloC3.3.0]octane, 4-C4'-chloro-2'- fluoro-5' - ( 1 -methyl-prop- 2-ynyloxy)phenyl]-3 , 5-dιoκo- 7-fluoro-1 ,4-dιazabιcycloC3.3.0]octane, 4-C4'-chloro- 2' -fluoro-5' - (prop-2-ynyloxy)phenyl]-3 , 5-dιoκo-7- fluoro-1 ,4-dιazabιcycloC3.3.0]octane, 4-C4'-chloro-2'- fluoro-5' - ( 1 -methyl-ethoxy )phenyl]-3 , 5-dιoxo-7 , 7- dιfluoro-1 ,4-dιazabιcycloC3.3.0]octane, 6-fluoro- 2- (7-fluoro-3-oxo-4-prop-2-ynyl-3 , 4-dι ydro-2H- benzoCI ,4]oxazιn-6-yl)-tetrahydro-pyrroloC 1 ,2- c3ιmιdazole-1 ,3-dione, 6,6-dιfluoro-2-(7-fluoro-3-oxo- 4-prop-2-ynyl-3 , 4-dιhydro-2H-beπzoC 1 , 4]oκazιn-6-yl)- tetrahydropyrroloCI ,2-c]ιmιdazole-1 ,3-dione (JUPAC) , 4- 2- hloro-4-fluoro-5- ( 6-fluoro- 1 , 3-dιακo- tetrahydropyrroloC 1 , 2-c]ιmιdazol-2-yl) phenoxy] but- 2-enoιc acid methyl ester (JUPAC) and stereoisomers thereof. Preferred is also a method in which the crop is peanut and the compound is applied preemergence . SUBSTITUTE SHEET Chemical examples Ex ample 1 A mixture of 2 ( R )-Carbomethoxy-4-fluoropyrrolidine (1 ,47 g, 0,01 ml) , triethylamine (50,0 mg , 0,5 m ol ) and toluene (30 ml) is prepared, and 4-chloro-2-fluoro-5--isopropoxyphenyl isocyanate (2,29 g, 0,01 mol ) dissolved in toluene (20 ml) is added dropwise. The reaction mixture is stirred for 5 h at reflux, then washed with 10 7. aqueous hydrochloric acid (3 x 10 ml) and water (3 x 10 ml) , dried over sodium sulfate, and filtered. After concentration of the filtrate by evaporation, the resulting residue is purified by silica gel chromatography . 2R-4-(4 ' -Chloro-2 ' -fluoro-5 ' -ιsopropoxyphenyl)-3,5- dioxo- 7-fluoro- 1 , 4-diazabicycloC .3.0 ]octane is obtained in the ammont of 2.58 g (75 '/ theoretical) as colourless crystals ( .p. 103 105 C) . SUBSTITUTE SHEET Example 2 : 2R-4-(4 ' -chloro-2 ' -fluoro-5 ' -carboιsopropoxyJ-3,5- dioxo-7-hydroxy- 1 , 4-diazabicycloC3.3.0 ]octane 3.71 g (0.01 mol) is dissolved in toluene (30 ml) and cooled to 0 - 5°c, before thionyl chloride (1 ,44 g, 12.0 mmol ) in toluene (10 ml) is added dropwise. The reaction mixture is refluxed for 15 h. The solvent and the excess of thionyl chloride is evaporated and the residue is purified by silica gel chromatography . 2R-4- ( 4 ' -chloro-2 ' -fluoro-5 ' -carboιsopropoxy)-7- chloro-3 , 5-dιoxo- 1 , 4-diazabicyclo 3.3.0] octane is obtained in the amount of 3, 19 g (82 7. of theoretical) as a colorless glass. E x a mpl e 3 : A mixture of 2 R- - ( 4 ' - chloro- 2 ' - luoro- 5 - carboιsopropoxyphenyl)- , 5-dιoxo-7-hydroxy-1 , 4 - dιazabιcyclo[3.3.0]octane (3 ,71 g, 0,01 mol) , triethylamine ( 1 ,41 g, 14.0 mol) and acetic acid anhydride ( 1 ,24 g, 12,0 mmol ) are added together in methylene chloride (30 ml) and toluene (60 ml) . The reaction mixture is refluxed for 13 h. cooled to room temperature and the organic layer is washed with water (3 x 15 ml) . The collected organic layers are dried over sodium sulfate, and filtered. After concentration of the iltrate by evaporation, the resulting residue is purified by silica gel chromatograph . 2R-4- ( 4 ' -Chloro-2 ' -fluoro- 5 ' -isopropoxyphenyl) -3 , 5- dιoxo-7-methylcarbonyloxy- 1 , -dιazabιcycloC3.3.0] octane is obtained in the amount of 2,84 g (69 7. of theoretical) as a colourless glass. SUBSTITUTE SHEET E x a mp l e : A mixture of 4-(4 ' -Chloro-2 -fluoro-5 -hydroxyphenyl)- 3 , 5-dιoxo-7-fluoro- 1 , 4-dιazabιcycloC3.3. Oloctane (3,03 g, 0,01 mol) , potassium carbonate (6,95 g, 0,05 mol) , propargyl bromide ( 1 , 78 g, 12,0 mmol ) and acetonitrile (60 ml) is stirred for 20 h at 20°C. The reaction mixture is acidified to pH = 2 with 5 7. aqueous hydrochloric acid, followed by extraction with ether (3 x 15 ml) . The ether layer is d ied over sodium sulfate, and filtered. After evaporation of the solvent, the residue is purified by silica gel chromatography . 4- ( 4 ' -Chloro-2 -fluoro-5 ' -propargyloxyphenyl ) -3 , 5- dιoκo-7- fluoro- 1 ,4-dιazabιcycloC3.3.0] octane is obtained in the amount of 3 , 16 g (93 7. of theoretical) in two fractions as two dia stereomers (or diastereomeric mixtures) . Fraction m. p 136 139°C C"] 2 D° + 45 , 1°C 20 2. Fraction: m.p. 143 - 145°C Cα] ■ 35 , 2 C SUBSTITUTE SHEET Analogously to Example 1 to 4 and in accordance with the general discription of the methods A to E in accordance with the invention, the compounds of general formula I listed in the following tables can be prepared : SUBSTITUTE SHEET Table 1 R A R 4 melting point °C H 7-F Cl H H 8-F Cl H H 7-C1 Cl C0 2 CH(CH 3 ) 2 H 8-C1 Cl 0CH(CH 3 ) 2 H 6-F Cl OCH C≡CH H 7-Br Cl 0CH(CH )C=CH SUBSTITUTE SHEET T a b l e 2 melting point °C 91-93 (R/S-Miκture at Pos . 2 and 7 ) 103-105 (2R, 7S-Konfι- 20 guration, α] =+48,8 ( c=0 , 5 in CH 2 C1 2 ) ) Cl OCH(CH 3 ) 2 glass (2R, 7R-Koπfi- 20 guration, Cα] =+38,3 (c= 1 in CH 3 OH) ) H Cl 0CH(CH 3 ) 2 glass H Cl OCH C=CH 143-145 (2S, 7R/S-Konfι- 20 guration, Cα] =-35,2 c=0 , 5 in CH 3 0H) ) SUBSTITUTE SHEET melting point Cl OCH C≡CH 136-139 (2R, 7R/S-Konfι- guration Cα]p°=+45, 1 (c=0 , 5 in CH 2 0H) ) Cl 0CH 2 C=CH glass (2R/S, 7R/S-Konfi- guration ) Cl 0CH(CH JC≡CH 133-139 (2S, 7R/S-Konfi- guration, ( c=0 , 5 in CH 3 OH) ) Cl OCH ( CH 3 )C=CH 121-124 ( 2R , 7R/S-Konfl- guration, Cα] 20=+41 ,5 ( c=0 , 5 in CH 3 OH ) ) Cl 0CH(CH 3 )C=CH glass (2R/S, 7R/S-Konfi- guration ) SUBSTITUTE SHEET melting point °C F H Cl CH 2 C0 2 H F H Cl SCH 2 C0 2 CH 3 CH. F H Cl OCH 2 C0N OCH 3 F H F Cl OC.CH )=N-OCH F H F Cl SCH C0 2 CH 2 C=CH F H F Cl OCHF F H F Cl 0CH 2 C( l) =CH 2 F H F Cl 0CF 2 CHFC1 F H F Cl NHSO CH F H F Cl NHS0 2 CH(CH 3 ) 2 F H F Cl NHS0 2 NHCH 3 F H F Cl CO CHICH ) oil (2R, 7R/S-Konfi- guration, Cα] 20=+32,4 ( c=0 , 5 in CH 2 C1 2 ) ) F H F Cl C0 2 CH 2 CH 2 CH 3 F H F Cl CO CH CF F H F Cl C0 2 CH(CH 3 ) 2 oil (2R/S, 7R/S-Konfi- guration ) F H F Cl C0 2 N(CH 3 ) 2 F H F Cl C0 2 CH(CH 3 )CH 2 CH 3 F H F Cl CO CH ( CH 3 ) CF 3 Cl CO, 2 SUBSTITUTE SHEET melting point °C F H F Cl C0 2 CH(CH 3 )CH 2 CH 3 Cl H F Cl Cl H F Cl OCHF. Cl H F Cl 0CH(CH„ ) oil (2R, 7S-Konfi- 3 '2 guration, rCαT] 20 =+4/ 11 , -7 (c=0 , 5 in CH 2 C1 2 ) ) Cl H F Cl OCF CHFC1 Cl H F Cl OCH CΞCH oil (2R, 7S-Konfi- 20 guration, Cα] =-35,8 (c=0 , 5 in CH 3 0H) ) Cl H F Cl OCH 2 C=CH glass (2R, 7S-Konfi- guration ) Cl H F Cl OCH 2 C=CH glass (2R/S, 7S-Konfi- guration ) Cl H F Cl 0CH 2 P(0) (C 2 H 5 ) 2 Cl H F Cl OCH ( CH 3 ) CHECH oil (2R, 7S-Konfι- guration ) Cl H F Cl 0CH(CH 3 )C=CH 130-145 (2S, 7S-Konfi- 20 guration, Co.] =-27,3 in CH 3 0H) ) Cl H F Cl 0CH 2 C(0)N(CH 3 )-, Cl H F Cl 0 ( CH 2 ) 2 OCH 2 CH 3 Cl H F Cl OCH CH=N-0CH CH=CH Cl H F Cl SCH C≡CH Cl H F Cl SCH CO H SUBSTITUTE SHEET R 2 R 4 R 5 melting point 0| Cl SCH 2 C0 2 CH 2 C=CH Cl NHSO CH Cl NHSO CF 3 Cl C0 2 CH(CH 3 ) 2 oil (2R, 7S-Konfi- guration, Cα] 20=+36,6 (c=0 , 5 in CH 2 C1) ) Cl C0 2 CH ( CH 3 ) CH 2 SCH 3 Cl CO CH(CH )CF 3 Cl C0 2 N(CH 3 ) 2 Cl C0 2 CH 2 C=CH Cl C0 2 CH(CH 3 JC≡CH Cl C0 2 CH 2 CF 3 Cl Cl CO, Cl H F Cl C0 2 (CH 2 > 2 CH 3 oil (2R. 7S-Konfi- guration ) Cl H F Cl CH=CHC0 2 CH 2 CH 3 0Si(CH 3 > 3 H F Cl C0 2 CH(CH 3 ) 2 oil (2R, 7S-Konfi- guration, Cα] 20=+29,5 (c=0 , 5 in CH 2 C1 2 ) ) Cl 0CH 2 C≡CH Cl 0CH(CH 3 )C=CH Cl C0 2 CH(CH 3 > 2 oil (2R, 7S-Konfi- guration ) SUBSTITUTE SHEET R 2 R* R 5 melting point °C 0C(0)CH 3 H F Cl C0 2 CH(CH 3 ) 2 oil (2R, 7R-Konfi- guration ) 0C(0)CH. Cl 0CH 2 C=CH 0C0 2 H 3 H F Cl 0CH(CH ) oil (2R, 7S-Konfi- guration ) OC0 2 CH 3 H F Cl OCH(CH 3 ) 2 oil (2R, 7R-Konfi- guration ) OS0 2 CH 3 H F Cl 0CH(CH 140-141 (2R, 7R-Konfi- 3' 2 20 guration, Ci] =+56,3 in CH 2 C1 2 ) ) OCH. H F Cl C0 2 CH(CH 3 ) 2 oil (2R, 7R-Konfi- 20 guration, Cα]- =+55,1 (c=0 , 5 in CH 2 C1 2 ) ) 0CH 3 H F Cl C0 2 CH 2 CH 2 CH 3 0CH 3 H F Cl OCH(CH 3 ) 2 0CH 3 H F Cl 0CH 2 C=CH OH H F Cl 0CH(CH 3 ) 2 63-65 (2R, 7R/S-Konfi- 20 guration, Cα] β =+47, 1 (c=0 , 5 in CH 3 0H) ) OH H F Cl C0 2 CH(CH 3 ) 2 45-48 ( 2S/ /S-Konfi- guratioπ) OH H H Cl H 161 ,5-163 OH H F Cl C0 2 CH(CH 3 ) 2 110-112 (2R/7R-Konfi guration, [α]^s +ag , ( c=0 , 5 in CH 3 0H ) 0CH 3 H F Cl 0CH(CH 3 )C=CH SUBSTITUTE SHEET R 2 R ' R 5 melting point °C OCH C≡CH H F Cl C0 2 CH(CH 3 ) 2 CH„ H F Cl C0 2 CH(CH 3 ) 2 C0 2 H H F Cl 0CH(CH 3'2 C0 2 H H F Cl C0 2 CH(CH 3 ) 2 Br H F Cl C0 2 CH(CH 3 ) 2 Br H F Cl C0 2 CH(CH 3 ) CH 2 CH 3 Br H F Cl 0CHF„ Br H F Cl OCH(CH„)„ 3 2 oil (2R, 7S-Konfι- guration, Cα] 20=+26,5 (c=0,5 in CH 2 C1 2 ) Cl 0CF 2 CHF 2 Cl OCH C≡CH Cl 0CH(CH JC≡CH Cl SCH 2 C0 2 H Cl HS0 2 CH 3 Cl NHSO CF Cl OCH(CH 3 ) 2 99-101 (2R-Konfi- 20 guration , Cα]^ =-34,2 (c=0 , 5 in CHC1 3 ) ) F F F Cl OCH 2 CH=CH 2 glass F F F Cl OCF 2 CH=CH 2 glass F F F Cl C0 2 CH(CH 3 ) 2 F F F Cl SCH 2 C0 2 CH 3 SUBSTITUTE SHEET R 2 R 4 R 5 melting F F F Cl 0CH 2 C≡CH F F F Cl 0CH(CH 3 )C≡CH F F Cl Cl C0 2 CH(CH 3 ) 2 F F Cl Cl 0CH 2 C=CH F F Cl Cl 0CH(CH 3 )C=CH SUBSTITUTE SHEET Ta ble 3 melting point °C Cl CH- glass (2R/S, 7S-Konfi- guration ) Cl CH. glass (2S, 7S-Konfi- guration Cα] 20 =+19 (c=0,5 in CH 2 C1 2 ) ) Cl CH; glass (2R, 7S-Konfi- guration, Cα] 20 =-16,6 (c=0 , 5 in CH 2 C1 2 ) SUBSTITUTE SHEET SUBSTITUTE SHEET SUBSTITUTE SHEET T a b l e 4 : w melting point °C F H F Cl H Cl S F H F Cl H CH 3 S F H F Cl H CH 2 H 3 S F H H SCH. H H s F H F Cl H Cl 0 F H F Cl H CH 3 0 Cl H F Cl H Cl s Cl H F Cl H CH 3 s Cl H F Cl H CH 2 CH 3 s Cl H H SCH. H H s Cl H F Cl H Cl 0 Cl H F Cl H CH 3 0 0CH- H F Cl H CH 3 s OCH. H F Cl H Cl s Br H F Cl H CH_ s SUBSTITUTE SHEET SUBSTITUTE SHEET Table 5 w melting point °C 0 s s s s s s s s s s s s s SUBSTITUTE SHEET SUBSTITUTE SHEET Table 6: SUBSTITUTE SHEET SUBSTITUTE SHEET Table 7 SUBSTITUTE SHEET Table 8 : R melting point °C SUBSTITUTE SHEET melting point °C F H F Cl CO,C 2 H 5 CH 3 F F F Cl C0 2 CH 3 CH 3 F F F Cl C0 2 CH 2 CH 3 CH 3 F F F Cl C0 2 CH 2 CH 2 CH 3 CH 3 F F F Cl C0 2 (CH 2 ) 3 CH 3 CH 3 F F Cl Cl C0 2 (CH 2 ) 3 CH 3 CH 3 SUBSTITUTE SHEET SUBSTITUTE SHEET Table 9 : R 1 melting point °C CH 3 Cl C0 2 CH(CH 3 ) 2 95-99 C2R-Konfi- guration, Cα] 20 =-14,3 (c=0 , 5 in CH 3 OH) ] CH 3 Cl C0 2 CH(CH 3 ) 2 97-99 C2S-Konfi- guration, α] 2π=+13,8 (c=0,5 in CH 3 OHJ] CH 3 F Cl OCH 2 C=CH CH 3 F Cl OCH ( CH 3 ) C≡CH CH 3 F Cl SCH 2 C0 2 CH 3 CH 3 F Cl 0CH 2 CH=CH 2 SUBSTITUTE SHEET Formulations Compounds of this invention will generally be used in formulation with an agriculturally suitable carrier comprising a liquid or solid diluent or an organic solvent. Use formulations include dusts, granules, baits, pellets, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates, dry flowables and the like, consistent with the physical properties of the active ingredient, mode of application and environmental factors such as soil type, moisture and temperature. Sprayable formulations can be extended in suitable media and used at spray volumes from about one to several hundred liters per hectare. High strength compositions are primarily used as intermediates for further formulation. The formulations will typically contain effective amounts of active ingredient, diluent and surfactant within the following approximate ranges which add up 100 weight percent. Weight Percent Active Inσredient Diluent Surfactant Wettable Powders 25-90 0-74 1-10 Oil Suspensions, 5-50 40-95 0-15 Emulsions, Solutions, (including Emulsifi¬ able Concentrates) SUBSTITUTE SHEET Acti e Ingredient Diluent Surfactant Ousts 1-25 70-99 0-5 Granules , Baits and Pellets 0.01 -99 5-99.99 0- 15 High Strength 90-99 0-10 0-2 Compositions Typical solid diluents are described in Watkins, et al. , "Handbook of Insecticide Oust Diluents and Carriers" , 2nd Ed. , Dorland Books, Caldwell , New Jersey. Typical liquid diluents and solvents are described in Marsden, "Solvents Guide" , 2nd Ed. , Interscience , New York, 1950. "McCutcheon ' s Detergents and Emulsifiers Annual" , Allured Publ. Corp. , Ridgewood, New Jersey, as well as Sisely and Wood, "Encyclopedia of Surface Active Agents" , Chemical Publ. Co. , Inc. , New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foam, caking, corrosion, microbiological growth, etc. Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blending and, usually, grinding as in a hammer mill or fluid energy mill. Water-dispersible granules can be produced be agglomerating a fine powder composition; see for example, Cross et al. , "Pesticide Formulations" , Washington, D.C. , 1988, pp 251 - 259. Suspensions are prepared by wet-milling; see, for SUBSTITUTE SHEET example, U.S. 3,060,084. Granules and pellets can be made by spraying the active material upon preformed granular carriers or by agglomeration techniques. See Browning, "Agglomeration' , Chemical Engineering, December 4, 1967, pp 147 - 148, "Perry ' s Chemical Engineer ' s Handbook" , 4th Ed. , McGraw-Hill, New York, 1963, pages 8 - 57 and following, and WO 91/13546. Pellets can be prepared as described in U.S. 4, 172,714. Water-dIspersible and water-soluble granules can also be p epared as taught in DE 32 46 493. For further information regarding the art of formulation, see U.S. 3,235,361 , Col. 6, line 16 through Col. 7, line 19 and Examples 10 - 41; U.S. 3,309,192, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41 , 52, 53, 58, 132, 138-140, 162-164, 166. 167 and 169-182; U.S. 2,891 ,855, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4; Kliπgman, "Weed Control as a Science" , John Wiley and Sons, Inc. , New York, 1961 , pp 81-96; and Hance et al. , "Weed Control Handbook" , 8th Ed. , Blackwell Scientific Publications, Oxford, 1989. In the following Examples, all percentages are by weight and all formulations are worked up in conventional ways. SUBSTITUTE SHEET E x a mpl e A : Wettable Powder 4- ( 4 ' -chloro-2 -fluoro-5 ' -carboisopropoxyphenyl ) - 7-chloro-3 , 5-dιoxo- 1 , -dιazabιcyclo- C3.3.0]octane 807. sodium alkylnaphthalenesulfonate 27. sodium ligmnsulfonate 27. syn hetic amorphous silica 3 7. kaolinite 137. The ingredients are blended, hammer-milled until all the solids are essentially under 50 microns, reblended and packaged. Example B : Wettable Pnwd r 4- ( 4 ' -chloro-2 ' -fluoro-5 ' -carboisopropoxyphenyl) - 7-chloro-3 , 5-dιoxo-1 , 4-dιazabιcyclo- C3.3.0]octane 507. sodium alkylnaphthalenesulfonate 27. low viscosity methyl cellulose 27. diatomaceous earth 467. The ingredients are blended, coarsely hammer-milled and then air-mill to produce p rticles essentially all below 10 microns in diameter. The product is reblended be o e packaging. SUBSTITUTE SHEET E x a m p J p G r a n u l e Wettable Powder of Example B 57 attapulgite granules 957 (U.S.S. 20-40 mesh; 0 ,84-0,42 mm) A slurry of wettable powder containing 25 7 solids is sprayed on the surface of attapulgite granules in a double-cone blender. The granules are dried and packaged . Example D Extruded Pellet 4-(4 ' -chloro-2 ' -fluoro-5 ' -carboιsopropoxyphenylJ- 7-chloro-3 , 5-dιoxo- 1 , 4-dιazabιcyclo- C3.3.0]octane 257. anhydrous sodium sulfate 107. crude calcium ligninsulfonate 57 sodium alkylnaphthalenesulfonate 17 calcium/magnesium bentomte 597. The ingredients are blended, hammer-milled and then moistened with about 127 water. The mixture is extruded as cylinders about 3 mm diameter which are cut to produce pellets about 3 mm long. These may be used directly after drying, or the dried pellets may be crushed to pass a U.S.S. No. 20 sieve (0.84 mm openings) . The granules held on a U.S.S. No. 40 sieve (0.42 mm openings) may be packaged for use and the fines rec cled. SUBSTITUTE SHEET E x ampl e E : Low Strength Granule 4 - ( ' -chloro- 2 ' -fluoro-5 ' -carboisopropoxyphenyl ) - 7-chloro-3 , 5-dioxo- 1 , 4-dιazabicyclo- C3.3.0]octane 1 N , N-dimethylformamide 97 attapulgite granules 907 (U.S.S. 20 to 40 sieve ) The active ingre ient is dissolved in the solvent and the solution is sprayed upon dedusted granules in a double-cone blender. Afte spraying of the solution has been completed, the blender is allowed to run for a short period and then the granules are packaged. Example F ranule 4- ( 4 ' -chloro-2 ' -fluoro- 5 ' -carboisopropoxyphenyl ) 7-chloro-3 , 5-dioxo- 1 , 4-diazabicyclo- C3.3.0]octane 807 wetting agent 17. crude lingninsulfonate salt (containing 107. 5-207 of the natural sugars) attapulgite clay 97 SUBSTITUTE SHEET The ingredients are blended and milled to pass through a 0 15 mm (100 mesh) screen. This material is then added to a fluid bed graπulator, the air flow is ad 3 usted to gently fluidize the material, and a fine spray of water is sprayed onto the fluidized material. The fluidization and spraying are continued until granules of the desired size range are made. The spraying is stopped, but fluidization is continued, σptionall with heat, until the water content is reduced to the desired level, generally less than 17. The material is then discharged, screened to the desired size range, generally 1.4 mm - 0.15 mm (14-100 mesh) , and packaged for use. Example : Aqueous Suspension 4- ( 4 -chloro-2 -fluoro-5 ' -carboisopropoxyphenyl ) 7-chloro-3 , 5-dioxo- 1 , 4-dιaz bιcyclo- C .3.0]octane 407 polyacrylic aci thickene 0.37. dodecylphenol polyethylene glycol ether 0.57. disodium phosphate 1 monosodium phosphate 0.57 polyvinyl alcohol 1.07. water 56.77 The ingredients are blended and ground together in a sand mill to produce particles essentially all under 5 microns in size . SUBSTITUTE SHEET E x ample H H gh Strength Concentrate 4- ( ' -chloro- ' -fluoro-5 ' -carboisopropoxyphenyl) 7-chloro-3 , 5-dioxo- 1 , 4-dιazabιcyclo- C3.3.0]octane 997 silica aerogel 0.57 synthetic amorphous silica 0.57. The ingredients are blended and ground in a hammer-mill to produce a material essentially all passing a U.S.S. No. 50 screen (0.3 mm opening) . The concentrate may be formulated further if necessary. Example I : Wettable Powder 4- ( 4 -chloro-2 ' -fluoro-5 ' -carboisopropoxyphenyl ) - 7 -chloro-3 , 5-dιoxo-1 , 4-dιazabιcyclo- [3.3.0] octane 907 dioctyl sodium sulfosuccinate 0.17 synthetic fine silica 9.97. The ingredients are blended and ground in a hammer-mill to produce particles essentially all below 100 microns. T e mate ial is sifted through a U.S.S. No. 50 screen (0.3 m ) and then packaged. SUBSTITUTE SHEET E x a mp l e J Wettable Powder 4- ( 4 ' -chloro-2 -fluoro-5 ' -carboisopropoxyphenyl 7-chloro-3 , 5-dιoxo-1 , 4-dιazabιcyclo- [3.3.0]octane 407 sodium ligmnsulfonate 207. montmorillonite clay 407 The ingredients are thoroughly blended, coarsely hammer-milled and then air-milled to produce particles essentially all below 10 microns in size. The material is reblended and then packaged. Example : Oil Suspension 4- ( 4 -chloro-2 -fluoro-5 ' -carboisopropoxyphenyl ) - 7-chloro-3 , 5-dιoxo-1 , 4-dιazabιcyclo- [3.3.0]octane 357 blend of polyalcohol carboxylic 67. esters and oil soluble petroleum sulfonates xylene 597 The ingredients are combined and ground together in a sand mill to produce particles essentially all below 5 microns . The product can be used directly, extended with oils, or emulsified in water. SUBSTITUTE SHEET Example L • Dust 4- ( 4 -chloro-2 ' -fluoro-5 ' -carboisopropoxyphenyl)- 7-chloro-3 , 5-dιoxo-1 , -dιazabιcyclo- C3.3.0]octane 107. attapulgite 107. pyrophyllite 807 The active ingredient is blended with attapulgite and then passed through a hammer-mill to produce particles substantially all below 200 microns. The ground concentrate is then blended with powdered pyrophyllite until homogeneous. Example M : Oil Suspension 4- ( ' -chloro-2 ' -fluoro-5 ' -carboisopropoxyphenyl) 7-chloro-3 , 5-dιoxo-1 ,4-dιazabιc clo- C .3.0]octane 257 polyoxyethylene sorbitol hexaoleate 57 highly aliphatic hydrocarbon oil 707 The ingredients are ground together in a sand mill until the solid particles have been reduced to under about 5 microns. The resulting thick suspension may be applied directly, but preferably after being extended with oils or emulsified in water. SUBSTITUTE SHEET U t i l i t y The compounds of the present invention are active herbicides. They have utility for broadspectrum preemergence and/or postemergence weed control in areas where complete control of all vegetation is desired, such as around industrial complexes, storage areas, parking lots, drive-in theaters, around billboards, fence rows, highway and railroad structures. Some of the compounds have utility for selective weed control in crops such as rice, wheat, barley, corn, soybeans, sugarbeets, cotton, peanut, all plantation crops including coffee, cocoa, sugarcane, oil palm, rubber, citrus, grapes, fruit trees, nut trees, banana, plantain, pineapple and conifers such as loblolly pine. The compounds can be applied as a preemergence and/or postemergence treatment using techniques of banding, directed sprays or broadcast applications. The rates of application for the compounds of the invention are determined by a number of factors, including their use as selective or general herbicides, the crop species involved, the types of weeds to be controlled, weather, climate, formulations selected, mode of application, amount of foliage present, etc. By selecting the appropriate rate which would be apparent to one skilled in the art, the compounds of this invention can be used in areas where complete control of all vegetation is desired, such as around fuel storage tanks, ammunition depots, industrial storage areas, oil well sites, drive-in theaters, around billboards, highway and railroad structures and in SUBSTITUTE SHEET fence rows. Alternatively, by selecting the proper rates and adjuvants, the compounds of this invention can be used for selective weeds control in peanuts and plantation corps such as citrus, sugarecane, coffee, oil palm, rubber, cocoa, grapes, fruit trees, nut trees, pineapple and banana. In general, the subject compounds are applied at levels of around 0.001 to 20 kg/ha, with a preferred rate range of 0.01 to 2 kg/ha rate. One skilled in the art can select the proper rates for a given situation. The compounds of this invention may be used in combination with other herbicides listed below. They are particularly useful in combination with tπazine, tπazole, uracil, urea, amide, carbamate, bipyπdyliu , phenoxy, sulfonylurea and lmidazole types for total vegetation control in plantation and other crops. The compounds may also be used in combination with mefluidide, glyphosate or gluphosinate . A mixture of one or more of the following herbicides with a compound of this invention may be particularly useful for weed control. Examples of other herbicides with which compounds of this invention can be formulated are: acetochlor, acifluorfen, acrolein, 2-propenal, alachlor, ametryn, amidosulfuron , ammonium sulfamate, amitrole, anilofos, asulam, atrazine, barban, benefin, bensulfuron methyl, bensulide, bentazon, benzofluor, benzoylprop, bifenox, bromacil, bromoxynil, bomoxynil heptanoate, bromoxynil octanoate, butachlor, buthidazole, butralin, butylate, cacodylic acid, SUBSTITUTE SHEET 2-chloro-N , N-dι-2-propenylacetamιde , 2-chloroallyl dlethyldithiocarbamate , chloramben , chlorbromuron , chloridazon, chlorimuron ethyl, chlormethoxynil , chlornitrofen , chloroxuron , chlorpropha , chlorsulfuron , chlortoluron , cinmethylin, ciπosulfuron , clethodium, clomazone, cloproxydim, clopyralid , calcium salt or methylarsonic acid, cyanazine, cycloate, cyluron, cyperquat, cyprazine, cyprazole, cypromi , dalapon, dazomet, dimethyl 2 , 3 , 5 , 6-tetrachloro- 1 , 4-benzenedιcarboxylate , desmedipham, des etryn, dicamba , dichlobenil, dichlorprop, diclofop, diethatyl, difenzoquat, diflufemcan , dimepiperate , diπitramine , dinoseb, diphenamid, dipropetryn, diquat, diuron, 2-methyl-4 , 6-dιπιtrophenol , disodium salt of methylarsonic acid, dymron , endothall, S-ethyl dipropylcarbamothioate , esprocarb, ethalfluralin , ethametsulfuron methyl, ethofumesate , fenac, fenoxaprop, fenuron, salt of fenuron and trichloroacetic acid, flamprop , fluazifop, fluazifop-P, fluchloralin , flumesulam, flumipropyn , fluometuron, fluαrochloπdone, fluorodifen, fluoroglycofen , flupoxam, fluπdone , fluoroxypyr , fluzasulfuron , fσmesafen, fosamine, glyphosate, haloxyfop, hexaflurate, hexazinone, imazamethabenz , imazapyr, imazaquin, imazamethabenz methyl, imazethapyr, imazosulfuron , loxynil , isopropalin, isoproturoπ, isouron, isoxaben, karbutilate, lactofeπ, lenacil, linuron, etobenzuron , metsulfuron methyl, methylarsonic acid, monoammonium salt of methylarsonic acid, ( 4-chloro-2-methylphenoxy ) acetic acid, S , S ' -dimethyl- - (difluoromethyl ) -4- ( 2-methylpropyl ) - 6- ( tπfluoromethyl ) -3 , 5-pyrιdιnedιcarbothιoate , SUBSTITUTE SHEET mecoprop, mefenacet, mefluidide, methalpropalin , methabenzthiazuron , metha , methazole, methoxuron, metolachlor, metribuzin , 1 , 2-dιhydropyrιdazιne-3 , 6- dione, molinate, monolinuron, monuron, monuron salt and trichloroacetic acid, monosodium salt of methylarsonic acid, napropamide, naptalam, neburoπ , nicosulfuron , nitralin , nitrofen, nitrofluorfen , norea , norflurazon, oryzalin , oxadiazon, oxyfluorfen, paraquat, pebulate, pendimethalin , perfluidone, phenmedipham, picloram, 5- C2-chloro-4- ( tπfluormethyl ) phenoxy]-2-nitroacetophenone oxime-O-acetic acid methyl ester, pretilachlor , pπmisulfuron , procyazine, profluralin, prometon, prometryn , proπamide , propachlor, propanil, propazine propham, prosulfalin, prynachlor, pyrazolate, pyrazon pyrazosulfuron ethyl, quinchlorac, quizalofop ethyl, πmsulfuron secbumeton , sethoxydim, siduron, simazine 1-(a ,a-dιmethylbenzyl)-3-(4- methylphenyl ) urea , sulfometuron methyl, trichloroacetic acid, tebuthiuron, terbacil, terbuchlor, terbuthylazine, terbutol, terbutryn, thifensulfuron methyl, thiobencarb, tri-allate, tπalkoxydim , tπasulfuron , tribenuron methyl, triclopyr, tridiphane, tπfluralin, tπmeturon , ( 2 , 4-dιchlorophenoxy ) acetic acid, 4-(2,4- dichlorophenoxy ) butanoic acid, vernolate, and xylachlor . The herbicidal properties of the subject compounds were discovered in a number of greenhouse tests. The test procedures and results are as follows: SUBSTITUTE SHEET Biolosάcai Tables compound 1 compound 8 SUBSTITUTE SHEET compound 9 compound 10 compound 1 1 coπpound 12 coπpound 13 coπpound 14 coπpound 15 coπpound 16 SUBSTITUTE SHEET coπpound 17 coπpound 18 coπpound 19 compound 23 conpound 24 SUBSTITUTE SHEET compound 26 coπpound 28 SUBSTITUTE SHEET Test procedure Seeds of crabgrass (Digitaπa spp. J , barnyardgrass (Echinochloa crus-galli) , giant foxtail (Setaπa fabeπi) , wild oats (Avena fatua) , cheatgrass (Bro us secalinus ) , velvetleaf (Abutilon theophrasti) , mormπgglory (Ipomoea spp. ) , cocklebur (Xanthium pensylvanicum) and sorghum. Nutsedge tubers were planted and treated preemergence with the test chemicals dissolved in a non-phytotoxic solvent. At the same time, these weed species were treated with a soil/foliage application. At the time of treatment, the plants ranged in height from 2 to 18 cm. Treated plants and controls were maintained in a greenhouse for sixteen days, after which all species were visually rated for response to treatment and compared to controls. The ratings, summarized in Table A - E 4 , are based on a numerical scale extending from 0 = no injury, to 10 = complete kill. The accompanying descriptive symbols have the following meanings: C = chlorosis/necrosis; B = burn H = formative effect; G = growth retardation; E = emergence inhibition. SUBSTITUTE SHEET 133HS 3±ruusans O Table C : postemergence (application rate 0.2 kg a.i./ha) Comp. Comp. Comp. Comp. Comp. Comp. Comp. U 1_8 u 20 Δ Z2 23 Corn 2B Wheat 3B Bamyardgrass 5B Cheat grass 3B Cocklebur 2B Morπingglory 5B Sorghum Giant foxtail 4B Crabgrass 5B Velvetleaf 3B Wild oats 2B Table D : preemergence (application rate 0.2 kg a.i./ha) Comp. Comp. Comp. Comp. Comp. Comp. Comp. 17 18 1 1 23 SUBSTITUTE SHEET Θ 0 Table E . : postemergence (rate 200 g/ha) SUBSTITUTE SHEET Table E preemergence (rate 200 g/ha) SUBSTITUTE SHEET Table E , : postemergence (rate 50 g/ha ) SUBSTITUTE SHEET Table E Δ : preemergence (rate 50 g/ha) SUBSTITUTE SHEET T e s t B Plastic tray liners with individual planting compartments were filled with planting medium and seeded separately with dallisgrass ( Pasoalum dilatatum) , bermudagrass ( C nodσn dactylon ) , annual bluegrass ( Poa annum) , guineagrass ( Panicum maximum) , broadleaf signalgrass ( Brachiaria platvphylla ) . goosegrass ( Eleusine indica ) . large crabgrass ( Digitar a sanguinalis ) , smooth crabgrass ( D . lschaemum ) , sandbur ( Cenchrus echinatus ) , itchgrass ( Rottboellia cochinchinensis ) , Texas panicum ( texanu ) , ohnson grass ( Sorghum halepense ) , alfalfa (Medicaαo sativa ) , peanut ( rac is hypogea ) , morningglory ( Ipomea sp. ) , ragweed (Ambrosia elatior ) , purslane ( portulaca oleracea ) and Pυeraπa lavanica . Tubers of purple nutsedge ( C perus rotundus ) and yellow nutsedge [_____, esculentus ) were also planted separately in individual pots. The plantings were staggered so that the preemergence and postemergence treatments with the compounds formulated in an non-phytotoxic spray solution were applied on the same day. Plants were visually rated compared with the appropriate controls at the end of the test. The ιn]urιng ratings were based on the scale of 0 to 100 where 0 indicates no effect, 20 indicates minimal effect and 100 indicates complete control. The variations in the results for the same compound could be due to the fact that the tests were conducted at different times of the year and on plants at different grouth stages. The results are shown in Tables SUBSTITUTE SHEET Table E Compound 4 250 250 g/ha Preemergence Postemergence Dallisgras s 0 0 Bermudagra ss 0 0 Annual bluegrass 0 0 Guineagrass 0 0 Broadleaf signalgrass 0 0 Goosegra s s 0 0 Large crabgrass 0 0 Smooth crabgrass 0 0 Sandbur 0 0 I tchgras s 0 0 Johnson grass 0 0 orningglory 0 0 Ragweed 0 0 Purslane 0 0 Alfalfa 0 0 Peanut 0 0 Purple nutsedge 0 0 Yellow nutsedge 0 0 SUBSTITUTE SHEET Table E. Compound 6 500 250 125 500 250 125 g/ha Preemergence Postemergence Dallisgra ss 100 100 100 Bermudagras s 100 100 100 Annual bluegrass 100 100 100 Guineagrass 100 100 100 Broadleaf signalgrass 100 100 90 Goosegra s s 100 100 100 Large crabgrass 100 100 100 Smooth crabgrass 100 100 100 Sandbur 100 100 100 Itchgra s s 100 100 80 Texas panicum 100 100 100 ohnson grass 100 100 80 Morningglory 100 100 90 100 100 100 Purslane 100 100 100 100 100 100 Alfalfa 100 100 100 100 100 100 Peanut 0 0 0 70 30 20 SUBSTITUTE SHEET Table E Dallisgra ss Bermudagrass Annual bluegrass Guineagrass Broadleaf signalgras Goosegra ss Large crabgrass Smooth crabgrass Sandbur Itchgrass Johnson grass Morningglory 100 100 Ragweed 100 100 Purslane 100 80 Alfal a 100 100 Peanut 0 30 SUBSTITUTE SHEET T a bl e E Dallisgra ss Bermudagrass Annual bluegrass Guineagras s Broadleaf signalgras Goosegra s s Large crabgrass Smooth crabgrass Sandbur Itchgrass Johnson grass Morningglory 80 100 Ragweed 100 100 Purslane 100 90 Alfalfa 100 100 Peanut 0 70 Purple nutsedge 40 20 Yellow nutsedge 80 80 SUBSTITUTE SHEET Table E Dallisgrass Bermudagra ss Annual bluegrass Guineagrass Broadleaf signalgra Goosegra s s Large crabgrass Smooth crabgrass Sandbur Itchgrass Johnson grass Morningglory 80 100 Ragweed 100 100 Purslane 100 100 Alfalfa 90 100 Peanut 20 60 Purple nutsedge 0 20 Yellow nutsedge 10 50 SUBSTITUTE SHEET Table E m n 11 Dallisgra ss Bermudagra s s Annual bluegrass Guineagrass Broadleaf signalgras Goosegrass Large crabgrass Smooth crabgrass Sandbur I tchgrass Johnson grass Morningglory 100 100 Ragweed 100 100 Purslane 100 90 Alfalfa 100 100 Peanut 60 100 Purple nutsedge 20 30 Yellow nutsedge 80 100 SUBSTITUTE SHEET Table E Compound 12 250 g/ha Postemergence Dallisgrass 20 Bermudagrass 0 Annual bluegrass 0 Guineagrass 0 Broadleaf signalgrass 0 Goosegrass 0 Large crabgrass 0 Smooth crabgrass 0 Sandbur 0 Itchgrass 0 Johnson grass 0 Morningglory 50 20 Ragweed 30 20 Purslane 100 20 Alfalfa 90 0 Peanut 20 0 Purple nutsedge 0 0 Yellow nutsedge 0 0 SUBSTITUTE SHEET Table E. 1 Dallisgra s s Bermudagra ss Annual bluegrass Guineagrass θroadleaf signalgrass Goosegras s Large crabgrass Smooth crabgrass Sandbur Itchgrass Johnson grass Morningglory 40 0 Ragweed 70 0 Purslane 100 30 Alfalfa 40 0 Peanut 0 0 Purple nutsedge 0 0 Yellow nutsedge 0 0 SUBSTITUTE SHEET Table E nd 1 - Dallisgra s s Bermudagra s s Annual bluegrass Guineagra s s Broadleaf signalgrass Goosegrass Large crabgrass Smooth crabgrass Sandbur Itchgra s s Johnson grass Morningglory 100 100 Ragweed 100 100 Purslane 100 90 Alfalfa 100 100 Peanut 50 100 Purple nutsedge 40 50 Yellow nutsedge 80 100 SUBSTITUTE SHEET Table E nd 22 Dallisgrass Bermudagrass Annual bluegrass Guineagrass Broadlea signalgrass Goosegra s s Large crabgrass Smooth crabgrass Sandbur Itchgrass Johnson grass Morningglory 80 60 Ragweed 100 70 Purslane 100 90 Alfalfa 60 90 Peanut 20 30 Purple nutsedge 0 0 Yellow nutsedge 0 0 SUBSTITUTE SHEET Table E, 4 Dallisgrass Bermudagra ss Annual bluegrass Guineagrass Broadleaf signalgras Goosegra ss Large crabgrass Smooth crabgrass Sandbur Itchgrass Johnson grass Morningglory 100 100 Ragweed 100 100 Purslane 100 90 Alfalfa 100 100 Peanut 60 100 Purple nutsedge 60 20 Yellow nutsedge 70 100 SUBSTITUTE SHEET Table E 5 Dallisgra ss Bermudagra ss Annual bluegrass Guineagrass Broadleaf signalgrass Goosegrass Large crabgra s s Smooth crabgrass Sandbur Itchgrass Johnson grass Morningglory 100 80 Ragweed 100 100 Purslane 100 90 Alfalfa 100 100 Peanut 60 70 Purple nutsedge 0 20 Yellow nutsedge 60 30 SUBSTITUTE SHEET T e s t C Windowsill flats were filled with planting medium and seeded with peanut (______ h pogea ) , gaint foxtail ( Setar faben ) , large crabgrass {_____ sanguinalis ) , guineagrass ( P . aximum) , Johnson grass (_S_j. halepense ) , nightshade (solanum mqrum) , morningglory ( Ipomea sp . ) and velvetleaf ( Abutlion theophrasti) . The plantings were treated preemergence with Compound 6 formulated in a non-phytotoxic spray solution. Plants were visually rated 21 and 40 days-after-treatment (DAT) and compared with the appropriate controls. The injuring ratings were based on the scale use in Test B. The results are shown in Table F. Test D Plastic tray liners with individual planting compartments were filled with planting medium and seeded with corn ( Zea mavs ) , soybean ( Glvcine ma . ) , peanut ( A . hvpogea ) , tomato ( L cooersium esenlentum) gaint foxtail ( S . aberi ) , guineagrass ( P . maximum) , Johnson grass (.S__- halepense ) , velvetleaf (A . theophrasti ) , morningglory, nightshade varieties - Solanum mqrum . S . n grum subsp. nigrum, S . ptvcanthus (green berries and black berries) , S . nigrum subsp. schetesn and _ ^ nigrum (atrazine tolerant ) . SUBSTITUTE SHEET The plantings were treated preemergence with Compound 6 formulated in a non-phytotoxic spray solution. Plants were visually rated at the end of the test and compared with the approprite controls. The in}ury ratings used in Test B were also employed in this test. The results are shown in Table G. T st E Rooted rough lemon cuttings were planted in 15-cm plastic pots. Another set of 11-cm plastic pots were filled with planting medium were seeded with balsam apple wine (Momordica charantia ) , sandbur ( C . echinatus ) , pigweed ( Amaranthus viπdus ) and guineagrass {£____ maximum) . This citrus was sprayed to simulate the trunk-to-trunk herbicide application method used in citrus groves, the weeds were treated preemergence and the balsam apple wine treated both preemergence and postemergence. All pots were treated with Compound 6 formulated in a non-phytotoxic spray solvent. Plants were visually rated 21 and 65 DAT and compared with appropriate controls. The injury rating scale used in Test B was also used. The results are shown in Table H . SUBSTITUTE SHEET Table F Compound 6 250 125 64 g/ha Preemergence Species 21 DAT Peanut 60 20 0 Giant foxtail 100 100 100 Large crabgrass 100 100 100 Guineagrass 100 100 100 Johnson grass 100 100 100 Nightshade 100 100 100 Morningglory 100 100 80 Velvetleaf 100 100 100 40 DAT Peanut 40 20 0 Giant foxtail 100 100 100 Large crabgrass 100 100 100 Guineagrass 100 100 100 Johnson grass 100 100 90 Nightshade 100 100 100 Morningglory 100 100 80 Velvetleaf 100 100 100 SUBSTITUTE SHEET Table G Compound 6 64 32 16 8 4 g/ha Preemergence peci s Corn Soybean Peanut Tomato Giant foxtail Guineagrass Johnson grass Velvetlea f Morningglory Solanum nigrum S . nigrum S. nigrum subsp. nigrum S. ptycanthus (green berries! S. nigrum subsp. schetesii S. ptycanthus (black berries! S. nigrum (atrazine tolerant SUBSTITUTE SHEET 1 ύ 1 Table H Compound 6 500 250 125 64 g a . l . /ha 21 DAT Post directed Citrus (rough lemon) 0 0 0 0 Preemergence Balsam apple vine 100 100 100 100 Sandbur 100 100 100 100 Pigweed 100 100 100 100 Guinea rass 100 100 100 100 Postemergence Balsam apple vine 100 100 100 100 65 DAT Post directed Citrus (rough lemon) 0 0 0 0 Preemergence Balsam apple vine 100 100 100 100 Sandbur 100 100 100 100 Pigweed 100 100 100 100 Guineagrass 100 100 100 100 Postemergence Balsam apple vine 100 100 100 100 SUBSTITUTE SHEET

Claims: C l a im s What is claimed is: 1. Bicyclic imides of formula I wherein the bond linking C-7 and C-8 may be single or double ; m ls 1 - 7 ; R can occupy one or more of the 2 or 6 - 8 positions and s independently selected from the group: hydroxy, halogen, CN , OR 3 , ( C,-C 4 Jalkyl, SfOJ^a, C 0R 3 , C(0)SR 3 and C(0)NR 11 R 12 ; Q-l Q-2 -3 SUBSTITUTE SHEET Q-5 Q-6 0-7 wherein R 3 is (Ci-Cβ Jalkyl, ( C 3 - C β ) cycloalkyl , ( C 3 -C 8 ) alkenyl , ( C 3 -C 8 ) alkynyl , (Cι-C β Jhaloalkyl, (C 2 -C β Jalkoxyalkyl, (C 2 -C_(Jcarbo y alkyl, (C 3 -C 8 Jalkoxycarbonylalkyl, (C -C β Jalkenyloxyalkyl, (C 4 -C β ) alkynyloxyalkyl, (C 3 -C e Ihaloalkoxyalkyl, (C 3 -C 8 Jtrialkylsilyl, ( C 3 -C 8 lcyanoalkyl, ( C 3 -C 8 l aloalkenyl, (C 3 -C 8 Jhaloalkynyl, (C 2 -C 8 lalkylcarbonyl, ( C 2 -C 8 ) alkoxycarbonyl , (C 2 -C 8 )haloalkoxycarbonyl, P(0) (0R 17 ) 2 , CHR 16 P(0) (OR 17 ) 2 or CH 16 P ( S ) ( OR 17 ) 2 , phenyl or benzyl optionally substituted with halogen, ( C, -C 3 ) alkyl , ( C 1 -C 3 ) haloalkyl or (C 1 -C 4 lalkoxy ; R 4 is hydrogen or halogen; R 5 is ( d -C 2 ) alkyl , ( C , -C 2 ) haloalkyl , 0CH 3 , SCH 3 , 0CHF 2 , halogen, C or Nθ 2 ; is hydrogen, ( C 1 -Ce ) alkyl , ( C 1 -C 8 ) haloalkyl , halogen, OR 10 , S(0> nR ιo COR 10 , C(0)SR 10 , C(0)NR 1 R 1 2 , CHO, CH=CHC0 2 R 10 , CO 2 =CR 13 R 14 , N0 2 , CN, NHS0 2 R 15 or NHS0 2 NHR 15 ; SUBSTITUTE SHEET R 7 and R β are independently ydrogen, ( C •, -C 3 ) alkyl , ( C , -C 3 ) haloalkyl or halogen; when Q is Q-2 or Q-6 ind R β together with carbon to which they are attached may be -Ce Jalkyl, ( C 1 - C 6 ) haloalkyl , Jalkoxyalkyl, (C 3 -Cβ Jalkenyl or ) alkynyl ; 1 o -Ce Jalkyl, ( C 3 -C 8 ) cycloalkyl , Jalkenyl, ( C 3 -C 8 ) alkynyl , Jhaloalkyl, ( C 2 -C 8 ) alkoxyalkyl , ) alkylthioalkyl , ) alkylsulfinylalkyl , ) alkylsulfonylalkyl , ) alkoxyalkoxyalkyl, lcycloalkylalkyl, (C 2 -C )carboxyalkyl, ) alkoxycarbonylalkyl , Jalkenyloxycarbonylalkyl, Jalkynyloxycarbonylalkyl, ) cycloalkoxyalkyl , ) alkenyloxyalkyl , ) alkynyloxyalkyl, Ihaloalkoxyalkyl, Jhaloalkenyloxyalkyl, Jhaloalkynyloxyalkyl, Jcycloalkylthioalkyl, Jalkenylthioalkyl, Jalkynylthioalkyl, Jtrialkylsilylalkyl, (C 3 -C β ) cyanoalkyl Jhalocycloalkyl, (C 3 -C B Jhaloalkenyl, ) alkoxyalkenyl , Jhaloalkoxyalkenyl, Jalkylthioalkenyl, (C 3 -C 8 Jhaloalkynyl, SUBSTITUTE SHEET ( Cs-Cβ lalkoxyalkynyl, ( C5-C8 ) haloalkoxyalkynyl , (C 5 -C 8 lalkylthioalkynyl, (C -C 8 Jalkylcarbonyl, CHR 16 C0R 17 , CHR 16 P (0 ) (OR 17 ) 2 , P(0) (OR 17 ) 2 , CHR 16 P(S) (0R 17 ) 2 , CHR 16 C(0)NR 1 1 R 1 2 , CHR 16 C ( 0 )NH 2 , (C 1 -C 4 )alkyl substituted with phenoxy or benzyloxy optionally substituted with halogen, (C-|-C 3 )alkyl or (Cι-C 3 )haloalkyl; benzyl optionally substituted with halogen, (C 1 -C 3 )alkyl or ( C 1 -C 3 ) haloalkyl ; or phenyl and pyridyl optionally substituted with halogen, ( i -C 3 ) alkyl . ( C , -C 3 ) haloalkyl or (C 1 -C 4 lalkoxy, R 1 1 and R 13 are independently hydrogen or (C 1 -C 4 Jalkyl; R 12 and R 14 are independently ( C 1 -C 4 ) alkyl , or phenyl optionally substituted with halogen, ( C!-C 3 ) alkyl, ( Ci -C 3 ) haloalkyl or (C 1 -C_»)al oxy; R 1 1 and R 12 may be taken together as -(CHjls-, - ( CH 2 ) 4 - or -CH2CH2OCH2CH 2 - , in which optionally one or more H-atoms may be replaced by (C1-C 3 Jalkyl, phenyl or benzyl; R 13 and R 14 may be taken together with the carbon to which they are attached to form ( C 3 -C 8 ) cycloalkyl; R 15 is ( Ci -C 4 ) alkyl or ( C ! -C 4 ) haloalkyl ; R 16 is hydrogen or ( C 1 -C 3 ) alkyl ; R 17 is ( C 1 -C 6 ) alkyl , ( C 3 -C 6 ) alkenyl or (C 3 -Cβ Jalkynyl; W 1s 0 or S ; n 1s 0 , 1 or 2 ; provided that SUBSTITUTE SHEET 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 A bond, then at least one R is other than hydroxy, halogen, (Cι-C 4 Jalkyl and (C 1 -C 4 )alkoxy. Bicyclic imides selected from the group consisting of 4-[4'-chloro-2'-fluoro-5'-(prop-2- ynyloxy)phenyl]-3,5-dιoxo-7-fluoro-1 ,4- dιazabιcyclo-C3.3.0]octane, 4-[4 '-chloro-2' - fluoro-5'- (1-methyl-prop-2-ynyloxy)phenyl]-3, 5- dιoxo-7-fluoro-1 ,4-dιazabιcyclo[3.3.0]octane, 4-[4' -chloro-2' -fluoro-5'- (2-prσpynyloxy)phenyl]- , 5-dιoxo-7-chloro- 1 , 4-dιazabιcyclo[3.3.0]octane , 4-[4'-chloro-2'-fluoro-5'-( 1 -methyl- ethoxy ) phenyl] -3 , 5-dioxo-7 , 7-dιfluoro- 1 , 4- diazabicyclo[3.3.0] octane and stereoisomers thereof . 3. Bicyclic imides according to Claim 1 or 2, cchhaarraacctteeπrizzed in that at least one R is in the 7-position . 4. Bicyclic imides according to Claim 3, characterized in that at least one R in the 7-posιtιon is fluoro, chloro or bromo 5. Bicyclic imides according to any one of Claims 1 to 4 , characterized in that it has 2R-configuration . SUBSTITUTE SHEET A method for preparing bicyclic imides according to Claim 1 or 2 comprising: (a ) reacting a compound of formula III Q—NCD III with a compound of formula IV IV wherein R=H or (C -C )alkyl, and cyclizing the intermediate . 7. A method for preparing bicyclic imides of formula la I α. wherein the bond linking C-7 and C-8 may be single or double ; m is 1 - 7 ; SUBSTITUTE SHEET can occupy one or more of the 2 or 6 - 8 positions and s independently selected from the group: hydroxy, halogen, CN , OR 3 , ( d -C 4 ) alkyl , S(0) nR 3 , COR 3 , CtOJSR 3 and C(0)NR f 1 R 12 ; Q-l Q-2 Q-3 wherein R 3 is (d-Cβ Jalkyl , ( C 3 -C 8 ) cycloalkyl , ( C 3 -C 8 ) alkenyl , ( C 3 -C 8 ) alkynyl , (d-CβJhaloalkyl, (C 2 -C β (alkoxyalkyl, (C 2 -C 4 )carboxy alkyl, (C 3 -C 8 Jalkoxycarbonylalkyl, (C 4 -C 8 J lkenyloxyalkyl, ( C 4 -C 8 ) alkynyloxyalkyl , (C 3 -C 8 Ihaloalkoxyalkyl, (C 3 -C 8 Jtrialkylsilyl, SUBSTITUTE SHEET (C 3 -C 8 (cyanoalkyl, (C 3 -C 8 Jhaloalkenyl, (C 3 -C 8 lhaloalkynyl, (C -C 8 Jalkylcarbonyl, ( C 2 -Cβ ) alkoxycarbonyl , (C 2 -C 8 Jhaloalkoxycarbonyl, P(0) (OR 17 ) 2 , CHR 16 P(0 ) (OR 17 ) 2 or CHR 16 P ( S ) ( OR 17 ) 2 , phenyl or benzyl optionally substituted with halogen, ( C ι -C 3 ) alkyl , (C 1 -C 3 I aloalkyl or (C 1 -C 4 )alkoxy; R 4 is h drogen or halogen; R 5 is (Cι-C 2 Jalkyl, ( C ,-C 2 ) haloalkyl , 0CH 3 , SCH 3 , 0CHF 2 , halogen, CN or N0 2 ; R 6 s hydrogen, ( C ,-C β ) alkyl , ( C 1 -C 8 ) haloalkyl , halogen, OR 10 , S ( 0) R i ° , COR 10 , CtOJSR 10 , n C(0)NR 1 1 R 12 , CHO, CH=CHC0 2 R 10 , CO 2 =CR 13 R 14 , N0 2 , CN, NHS0 2 R 15 or NHS0 2 NHR 15 ; R 7 and R 8 are independently hydrogen, ( C ! -C 3 ) alkyl , ( C 1 -C 3 ) haloalkyl or halogen; when Q is Q-2 or Q-6, R 7 and R β together with the carbon to which they are attached may be C=0; R 9 is ( Ci -C 6 ) alkyl , ( C -C 6 ) haloalkyl , (C∑-CβJalkoκyalkyl, (C 3 - 6 Jalkenyl or ( C 3 -C 6 ) alkynyl; R 10 is ( Ci -C 8 Jalkyl, ( C 3 - C 8 ) cycloalkyl , ( C 3 -C β ) alkenyl , ( C 3 -C β ) alkynyl , (Cι-C β Jhaloalkyl, (C 2 -C β Jalkoxyalkyl, (C 2 -C 6 )alkylthioalkyl, (C ∑ -Cβ Jalkylsulfinylalkyl, (C 2 -C 8 Jalkylsulfσπylalkyl, (C 3 -C 8 Jalkoxyalkoxyalkyl, (C -C 8 Jcycloalkylalkyl, (C 2 -C 4 Jcarboxyalkyl, ( C 3 -Cβ ) alkoxycar onylalkyl , ( Cβ-Ce ) alkenyloxycarbonylalkyl , SUBSTITUTE SHEET ( C & -C 8 ) alkynyloxycarbonylalkyl , ( C 6 -C 8 ) cycloalkoxyalkyl , (C 4 -Cβ Jalkenyloxyalkyl, (C 4 -Ce ) alkynyloxyalkyl, ( C 3 -Cβ Ihaloalkoxyalkyl, ( C 4 -Cβ ) haloalkenyloxyalkyl , ( C -C 8 ) haloalkynyloxyalkyl , ( Cβ-Cβ ) cycloalkylthioalkyl , (C 4 -C 8 Jalkenylthioalkyl, ( C 4 - C B Jalkynylthioalkyl, (C -C 8 Jtrialkylsilylalkyl, (C 3 -C β ) cyanoalkyl. ( 3 - C B Jhalocycloalkyl, (C 3 -C β Jhaloalkenyl, < C 5 -Cβ ) alkoxyalkenyl , (C 5 -C 8 Jhaloalkoxyalkenyl, (C 5 -C 8 Jalkylthioalkenyl, (C 3 -C 8 Jhaloalkynyl, ( C 5 -C 8 ) alkoxyalkynyl , (Cs-Cβ Jhaloalkoxyalkynyl, (C 5 -Cβ )alkylthιoalkynyl, (C ∑ -CβJalkylcarbonyl, CHR 16 C0R 17 , CHR 16 P(0) (OR 17 ) 2 , P(0) (0R 17 ) 2 , CHR 16 P(S) (0R 17 ) 2 , CHR 16 C(0)NR 1 1 R 12 , CHR 16 C (0 )NH 2 , (C 1 -C 4 )alkyl substituted with phenoxy or benzyloxy optionally substituted with halogen, (C 1 -C 3 Jalkyl or ( C 1 - C 3 ) haloalkyl ; benzyl optionally substituted with halogen, (Cι-C 3 )alkyl or ( C , -C 3 ) haloalkyl ; or phenyl and pyridyl optionally substituted with halogen, ( C , - C 3 Jalkyl , ( C, -C 3 ) haloalkyl or ( C ! -C 4 ) alkoxy ; R 11 and R 13 are independently hydrogen or (Cι-C 4 )alkyl; R 12 and R 14 are independently ( C 1 -C 4 ) alkyl , or phenyl optionally substituted with halogen, SUBSTITUTE SHEET I 11 ( Ci -C 3 ) alkyl , ( C -C 3 ) haloalkyl or ( C ι -C 4 ) alkoxy ; R 1 1 and R 1 2 may be taken together as -(CH 2 ) 5 - , -(CH 2 ) - or -CH2CH2OCH2CH2- , in which optionally one or more H-atoms may be replaced by ( C 1 - C 3 ) alkyl , phenyl or benzyl; R 13 and R 14 may be taken together with the carbon to which they are attached to form (C 3 -Cβ Jcycloalkyl; R 15 is (C 1 -C 4 )alkyl or ( C 1 - C 4 ) aloalkyl ; R 16 is hydrogen or ( C . -C 3 ) alkyl ; R 17 is ( Cι-C 6 ) alkyl , ( C 3 - C 6 ) alkenyl or ( C 3 -C 6 ) alkynyl ; is 0 or S ; n is 0 , 1 or 2 ; selected from the group consisting of (b) or (c) : (b) reacting a compound of formula IV, wherein R=H or ( C1 -C 4 ) alkyl , with phosgene and then with an amine of formula VI VI to form compounds of formula VII , I O^NH Q and cyclizing the compounds of formula VII , or SUBSTITUTE SHEET (c) reacting a compound of formula III with a compound of formula VIII VIII to form a compound of formula IX, DC and hydrolyzing and cylizing the compound of formula IX. 8. A method for making bicyclic imides of Claim 2 or of formula I of Claim 1 comprising preparing a compound of formula II wherein R 1 is R A R 2 is R and H comprising reacting a compound of formula X wherein R=H or ( C ,-C 4 ) alkyl , with a compound of general formula III, Q—NCO III and converting the reaction product formed thereby . A method for making compounds of formula la la. wherein the bond linking C-7 and C-8 may be single or double ; m is 1 - 7 ; SUBSTITUTE SHEET R M can occupy one or more of the 2 or 6 - θ positions and is independently selected from the group: hydroxy, halogen, CN, OR 3 , ( C 1 -C 4 Jalkyl , S(0) 3 , COR 3 , C(0)SR 3 and n C ( O JNR 1 1 R 1 2 is Q-I Q-2 Q-3 Q-* Q-5 Q-6 0-7 wherein R 3 is ( 0,-08 Jalkyl, ( C 3 -C β ) cycloal k yl , ( C 3 -C 8 Jalkenyl, ( C 3 -C 8 ) alkynyl , iC.-Ce ) haloalkyl, (C 2 -C 8 ) alkoxyalkyl SUBSTITUTE SHEET (C 2 -C 4 )carboxy alkyl, (C 3 -C 8 Jalkoxycarbonylalkyl, (C 4 -C 8 Jalkenyloxyalkyl, ( 4 - C β ) alkynyloxyalkyl , (C 3 -C 8 Ihaloalkoxyalkyl, (C 3 -C 8 Itrialkylsilyl, ( C 3 -Cβ Jcyanoalkyl, ( C3 -Cβ lhaloalkenyl, (C 3 -C 8 )haloalkynyl, (C -C 8 Jalkylcarbonyl, (C 2 -C β Jalkoxycarbonyl, (C 2 -C 8 Jhaloalkoxycarbonyl, P(0) (OR 17 ) 2 , CHR 16 P(0) (OR 17 ) 2 or CHR 16 P ( S ) ( OR 17 ) 2 , phenyl or benzyl optionally substituted with halogen ( C , - C 3 ) alkyl , ( C 1 -C 3 ) haloalkyl or (C 1 -C 4 )alkoxy; R 4 is hydrogen or halogen; R 5 is ( C 1 -C 2 Jalkyl , ( C ,-C 2 ) haloalkyl , 0CH 3 , SCH 3 0CHF 2 , halogen, CN or N0 2 ; R 6 is OR 10 , S ( 0 ) n Rio NHSO 2 R 15 or NHSO ∑ NHR 15 ; R 7 and R 8 are independently hydrogen, ( C , -C 3 ) alkyl , ( C 1 - C 3 ) haloalkyl or halogen; when Q is Q-2 or Q-6, R 7 and R fl together with the carbon to which they are attached may be C=0; R is ( C , -C 6 ) alkyl , ( C ,-C 6 ) haloalkyl , (C 2 - 6 Jalkoxyalkyl, (C 3 -C 6 Jalkenyl or (Ca-CβJalkynyl; R 10 is (Ci -C 8 Jalkyl, ( C 3 -C β ) cycloalkyl , ( C 3 -C β ) alkenyl, ( C 3 -C β ) alkynyl , ( d -C β Jhaloalkyl, (C 2 -C β Jalkoxyalkyl, (C 2 -C 6 )alkylthioalkyl, (C 2 - 3 Jalkylsulfinylalkyl, (C 2 -C 8 Jalkylsulfonylalkyl, (C 3 -C 8 Jalkoxyalkoxyalkyl, (C 4 -C 8 Jcycloalkylalkyl, { C 2 - C 4 Jcarboxyalkyl, SUBSTITUTE SHEET ( c 3 -c 8 alkoxycarbonylalkyl , (C 6 -C 8 alken loxycarbonylal yl , <c 6 -c 8 alkynyloxycarbonylalkyl , (C 6 -C 8 cycloalkoxyalkyl, ( C 4 -C 8 alkenyloxyalkyl , ( C 4 -C β alkynyloxyalkyl, (C 3 -C β haloalkoxyalkyl , (C 4 -C 8 haloalkenyloxyalkyl , (C 4 -C 8 haloalkynyloxyalkyl , ( C 6 -C 8 cycloalkylthioalkyl, ( c 4 -c θ alkenylthioalkyl , (C 4 -C 8 alkynylthioalkyl , (C 4 -C 8 trialkylsilylalkyl, (C 3 -Cβ Jcyanoalkyl, ( C3-C8 halocycloalkyl, (C 3 -C β Jhaloalkenyl, s C 5 -C β alkoxyalkenyl , (C 5 -C β haloalkoxyalkenyl , ( 0 5 -Cβ alkylthioalkenyl, (C 3 -C 8 Jhaloalkynyl, ( C 5 -C 8 alkoxyalkynyl , ( c 5 -c 8 haloalkoxyalkynyl, (C 5 -C 8 alkylthioalkynyl, ( C.-CB lalkylcarbonyl, CHR 16 COR 17 , CHR 16 P(0) (0R 17 ) 2 , P(0) (0R 17 ) 2 . CHR 16 P S) (0R 17 ) 2 , CHR 6 C(0)NR 1 1 R 1 - , CHR 16 C 0)NH 2 , (C 1 -C 4 )alkyl substituted with phenoxy or benzyloxy optionally substituted with halogen, (Cι-C 3 )alkyl or ( C 1 -C 3 Jhaloalkyl; benzyl optionally substituted with halogen, (d-C 3 )alkyl or ( C 1 -C 3 Jhaloalkyl; or phenyl and pyridyl optionally substituted with halogen, ( Ci -C 3 ) alkyl , ( C .- C 3 ) haloalkyl or ( C 1 - C 4 ) alkoxy; R 1 and R 13 are independently hydrogen or ( Ci -C 4 ) alkyl ; SUBSTITUTE SHEET R 12 and R 14 are independently (C 1 -C 4 )alkyl, o phenyl optionally substituted with halogen, (Cι-C 3 Jalkyl, (Cι-C 3 )haloalkyl or ( Ci - C 4 ) alkoxy ; R 1 1 and R 1 2 may be taken together as -(CH ∑ Js- , -(CH 2 ) 4 - or -CH2CH2OCH2CH2- , in which optionally one or more H-atoms may be replaced by (d-C 3 )alkyl, phenyl or benzyl; R 13 and R 14 may be taken together with the carbon to which they are attached to form (C 3 -C 8 Jcycloalkyl; R 15 is (C 1 -C 4 )alkyl or ( C ,- C 4 ) haloalkyl ; R 16 is hydrogen or (d-C 3 )alkyl; R 17 is ( C, -C 6 Jalkyl, ( C 3 -C 6 ) alkenyl or (C 3 -C 6 Jalkynyl; W is 0 or S ; n is 0 , 1 or 2 ; comprising reacting a compound of the formula XIII wherein Y = 0, S, NH with a halide selected from the group R 10 -Z SO ∑ -Z and R 15 NHS0 2 -Z wherein 2 is chlorine, bromine or iodine SUBSTITUTE SHEET 10. A composition for controlling weeds comprising an effective amount of a compound of Claim 1 or 2 and at least one carrier therefor. 11. A method for controlling weeds comprising applying to the locus to be protected an effective amount of the compound of Claim 1 or 2. 12. A method for controlling weeds in plantation crops and peanut comprising applying to the locus to be protected an effective amount of a compound of formula Ia : I . wherein the bond linking C-7 and C-θ may be single or double ; R can occupy one or more of the 2 or 6-8 positions and is independently selected from the group: hydroxy, halogen, CN, OR 3 , (d-C 4 )alkyl, StOl^a, COR 3 , C(0)SR 3 , an d CtOJNR 11 R 12 SUBSTITUTE SHEET Q-l Q-2 Q-3 Q^» Q-5 Q-6 Q-7 wherein R 3 is ( C, -C 8 Jalkyl ( C 3 -C 8 ) cycloalkyl , (C 3 -Ca Jalkenyl, (C 3 -C 8 )alkynyl, ( d -C θ Jhaloalkyl, (C -C 8 Jalkoxyalkyl, (C 2 -C 4 )carboxy alkyl, (C 3 -C B ) alkoxycarbonylalkyl, (C 4 -C 8 Jalkenyloxyalkyl, (C 4 -C 8 ) alkynyloxyalkyl, (C 3 -C β Ihaloalkoxyalkyl, ( C 3 -Cβ Jtrial ylsilyl, (C 3 -Ce (cyanoalkyl, (C 3 -C 8 Jhaloalkenyl, (C 3 -C β Jhaloalkynyl, (C 2 -C β )alkylcarbonyl, (C 2 ~C 8 Jalkoxycarbonyl, (C ∑ -Cβ Jhaloalkoxycarbonyl, P(0) (OR 17 ) 2 . CHR 16 P ( 0 ) (OR 17 ) 2 or CHR 16 P ( ) ( OR 17 ) 2 , phenyl or benzyl optionally substituted with halogen ( d-C 3 )alkyl , ( C , -C 3 ) haloalkyl or ( C 1 -C 4 ) alko y; SUBSTITUTE SHEET R 4 is hydrogen or halogen; R 5 is (d-C 2 Jalkyl, ( C -C 2 ) haloalkyl , 0CH 3 , SCH 3 , 0CHF 2 , halogen, CN or N0 2 ; is hydrogen, ( C i -C 8 ) alkyl , ( C 1 -C 8 ) haloalkyl , halogen, OR 10 , S(0) R'», COR 10 , C(0)SR 10 . C(0)NR 1 1 R 12 , CHO, CH=CHC0 2 R 10 , CO 2 N=CR 13 R 14 , N0 2 , CN, NHS0 2 R 15 or NHSO ∑ NHR 15 ; and R 8 are independently hydrogen, ( C 1 -C 3 ) alkyl , ( C 1 -C 3 ) haloalkyl or halogen; when Q is Q-2 or Q-6, R 7 and R 8 together with the carbon to which they are attached may be C=0; is ( C . -C 6 ) alkyl , ( C . -C 6 ) haloalkyl , ( C 2 -C 6 ) alkoxyalkyl , ( C 3 -C 6 ) alkenyl or ( C 3 -C 6 Jalkynyl; is ( Ci -C β Jalkyl, ( C 3 -C 8 ) cycloalkyl , (C 3 -C β ) alkenyl, ( C 3 -C 8 ) alkynyl , ( C1 -C β Jhaloalkyl, (C 2 -C 8 Jalkoxyalkyl, (C 2 -C 6 )alkylthioalkyl, (C 2 -C a Jalkylsulfinylalkyl, (C 2 -C 8 Jalkylsulfonylalkyl, (C 3 -C 8 Jalkoxyalkoxyalkyl, (C -C 8 Jcycloalkylalkyl, (C 2 -C 4 Jcarboxyalkyl, (C 3 -C 8 ) alkoxycarbonylalkyl, (C 6 -Cβ ) alkenyloxycarbonylalkyl , (Cβ-Cβ Jalkynyloxycarbonylalkyl, (Ce-C e Jcycloalkoxyalkyl, (C 4 -Cβ Jalkenyloxyalkyl, (C 4 -C 8 ) alkynyloxyalkyl, (C 3 -C 8 Ihaloalkoxyalkyl, (C -Cβ Jhaloalkenyloxyalkyl, (C 4 -C 8 Jhaloalkynyloxyalkyl, (C 6 -C β Jcycloalkylthioalkyl, SUBSTITUTE SHEET ( C4-Cβ lalkenylthioalkyl, (C 4 -C B lalkynylthioalkyl, (C 4 -C β Jtrialkylsilylalkyl, (C 3 -C β ) cyanoalkyl, (C 3 -C 8 Jhalocycloalkyl, (C 3 -C fl Jhaloalkenyl, ( C5-C 8 Jalkoxyalkenyl, ( C 5 -C 8 Jhaloalkoxyalkenyl , (C 5 -C 8 Jalkylthioalkenyl, (C 3 -C β Jhaloalkynyl, ( C 5 -C 8 Jalkoxyalkynyl, (Cs-Cβ Jhaloalkoxyalkynyl, (C 5 -C 8 Jalkylthioalkynyl, (C 2 -C a Jalkylcarbonyl, CHR 16 C0R 17 , CHR 16 P(0) (OR 17 ) 2 , P(0) (0R 17 ) 2 , CHR 16 P(S) (OR 17 ) 2 , CHR 16 C. (0)NR 1 R 12 , CHR 16 C (0)NH 2 , (d-C 4 )alkyl substituted with phenoxy or benzyloxy optionally substituted with halogen, (d-C 3 )alkyl or ( C \ -C 3 ) haloalkyl; benzyl optionally substituted with halogen, (C-i-CaJalkyl or ( C ι -C 3 ) haloalkyl ; or phenyl and pyridyl optionally substituted with halogen, ( d -C 3 Jalkyl , ( Ci -C 3 ) haloalkyl or (C 1 -C 4 )alkoxy; R 11 and R 13 are independently hydrogen or (d-C 4 )alkyl; R 12 and R 14 are independently ( C 1 -C 4 ) alkyl , or phenyl optionally substituted with halogen, ( 0,-03 Jalkyl, ( C ,-C 3 ) haloalkyl or ( C -0 4 ) alkoxy ; R 11 and R 12 may be taken together as -(CH 2 )s-, -(CH 2 ) 4 - or -CH 2 CH 2 0CH 2 CH 2 - , in which optionally one or more H-atoms may be replaced by (C 1 -C3 Jalkyl, phenyl o benzyl; R 13 and R 14 may be taken together with the carbon to which they are attached to form ( C 3 -C 8 ) cycloalkyl; SUBSTITUTE SHEET R 1 S is (Cι-C 4 )alkyl or ( C , -C 4 J haloalkyl ; R 16 is hydrogen or ( C 1 -C 3 ) alkyl ; R 17 is ( Ci -C 6 ) alkyl ; ( C 3 -C 6 ) alkenyl or (C 3 -C 6 Jalkynyl; W is 0 or S ; n is 0 , 1 , or 2. 13. A method of Claim 12 wherein the plantation crop is selected from the group consisting of citrus, sugarcane, coffee, banana, oil palm, grapes and rubber . 14. A method of Claim 12 or 13 employing at least one of the compounds of the group consisting of 4-C4'- chloro-2'-fluoro-5'- ( 1 -methylethoxy Jphenyl]- ,5-dioxo-7-fluoro-1 , 4-diazabicyclo[3.3.0]octane, 4-C ' -chloro-2'-fluoro-5'- ( 1-methyl-prop-2- ynyloxy)phenyl]-3 , 5-dioxo-7-fluoro-1 , 4- diazabicyclo[3.3.0]octane, 4-[ '-chloro-2' -fluoro- 5' - (prop-2-ynyloxy)phenyl]-3 , 5-dioxo-7-fluoro- 1 ,4-dιazabicyclo[3.3.0]octaπe, 4-[4'-chloro-2'- fluoro-5'- ( 1 -methyl-ethoxy )phenyl]-3 , 5-dioxo-7 , 7- difluoro-1 ,4-dia∑abicyclo[3.3.0]octane, 6- luoro-2- (7-fluoro-3-oκo-4-prop-2-ynyl-3 , 4- dihydro-2H-beπzo[ 1 , ]oxazin-6-yl)-tetrahydro- pyrrolo[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-dιoxo- tetrahydropyrrolo[1 ,2-c] imidazol-2-yl) phenoxy] but- SUBSTITUTE SHEET 2-enoιc acid methyl ester (JUPAC) and s ereoisomers thereof. 15. A method of Claim 12 wherein the crop is peanut and the compound is applied preemergence. 16. Use of compounds of claim 1 or 2 as herbicide 17. Use of compounds of formula la for controlling weeds in plantation crops and peanut: wherein X x represents C=C or C-C; m is 5 or 7 A R fills up the free 2, 6-8 positions and are, independently of each other, hydrogen, hydroxy, halogen, CN, OR 3 , (C -C. Jalkyl, S(0) R 3 , COR 3 , 1 4 n C(0)SR 3 , C(0)NR 11 R , with the measure that at A least one R is not hydrogen; SUBSTITUTE SHEET Q-l Q-2 Q-J Q Q-5 Q-6 Q-7 wherein is ( C 1 -c 8 Jalkyl, ( C 3 -Cg ) cycloalkyl (C 3 -Cg)alkenyl, ( C 3 ~Cg ) alkynyl . (C, -C. Jhaloalkyl (C 2 -Cg)alkoxyalkyl, 1 o ( C -C, ) carboxy alkyl, Z 4 (C -C ) alkoxycarbonylalkyl, SUBSTITUTE SHEET (C -C )alkenyloxyalkyl, (C.-C.) alkynyloxyalkyl (C -CgJhaloalkoxyalkyl, (C 3 -C a )trialkylsilyl, ( ^-c Jcyanoalkyl, (C 3 -Cg)haloalkenyl, (C -Cg)haloalkynyl, (C 2 -Cg)alkylcarbonyl, 'C^-C o Jalkoxycarbonyl, 17 (C -Cgjhaloalkoxycarbonyl, P(0) (OR 2' CHR 16 P(0) (OR 17 J or CH 16 P ( S )OR 17 ) , phenyl or benzyl optionally substituted with halogen, (C -C 3 )alkyl, ( C 1 -C 3 ) haloalkyl or IC.-C, I alkoxy ; is hydrogen or halogen; is (C. -c 2 Jalkyl, ( C 1 -C 2 Jhaloalkyl 0CH 3 , SCH 3 , OCHF halogen, CN or NO R 6 is hydrogen, ( C ^-Cg ) alkyl , ( C 1 -Cg ) haloalkyl , halogen, OR 10 , S(0) R 10 , COR 10 , C(0JSR 10 , n C(0)NR 11 R 12 , CHO, CH-CHCO R 10 , CO N=CR 13 U , NO CN, NHSO.R 15 or NHSO NHR 15 ; R 7 and R8 are independently hydrogen, ( C 1 -C_ ) alkyl, ( C. -C- ) haloalkyl or halogen; when Q is Q-2 or Q-6, R and R together with the carbon to which they are attached may be C=0; R 9 is ( C ,-Cg) alkyl , ( C 1 -Cg ) haloalkyl , ( C -C_ ) alkoxyalkyl , ( C -C g ) alkenyl or (C 3 -Cg Jalkynyl; R 10 is ( C 1 - g Jalkyl, ( C 3 -Cg )cycloalkyl , (C -C Jalkenyl, ! C 3 -Cg ) alkynyl , ( C -Cg Jhaloalkyl, ( C 2 ~C β ) alkoxyalkyl , (C2-C-b)alkylthiσalkyl, ( C 2 -Cg Jalkyl sulfinylalkyl, ( C -C )alkylsulfonylalkyl, (C -C Q )alkoxyalkoxyalkyl, j a (C -C )cycloalkylalkyl, (C.-C Jcarboxyalkyl, ( C -C„ ) alkoxycarbonylalkyl , SUBSTITUTE SHEET ( Cb. -Co β ) alkenyloxycarbonylalkyl , ( Cb_ -Co a Jalkynyloxycarbonylalkyl, ( Cb -co n ) cycloalkoxyalkyl , (C -Cg)alkenyloxyalkyl, ( C^-Cg ) alkynyloxyalkyl, ' c 3 -C )haloalkoxyalkyl, (C 4, -Co„ ) haloalkenyloxyalkyl , (C, -C. ) haloalkynyloxyalkyl , 4 o (C -C.)cycloalkylthioalkyl, b o (C, -C 0 ) alkenylthioalkyl , 4 o (C, -C 0 ) alkynylthioalkyl , 4 σ (C. -C. ) trialkylsilylalkyl , ( C_-C„ ) cyanoalkyl , -. o J o {Cr J,-Co B Jhalocycloalkyl, (C_J-C0 0 )halαalkenyl, !C C D-CO 0 Jalkoxyalkenyl, (C c D-CO aloalkoxyalkenyl, ( C,--Cg)alkylthιoalkenyl, (C 3 -Cg)haloalkynyl, Jalkoxyalkynyl , (C c D-C.O) aloalkoxyalkynyl, (C -C-)alkylthioalkynyl, (C 2 -Cg)alkylcarbonyl, CHR 16 COR 17 , CHR 16 P(0) (OR 17 J , P(0) (0R 17 ) 2 , CHR 16 P(S)(0R 17 ) 2 , CHR 16 C(0)NR 11 R 12 , CHR 16 C(0)NH 2 , (C 1 -C 4 Jalkyl substituted with phenoxy or benzyloxy optionally substituted with halogen, (C_ j -C 3 )alkyl or ( C -C 3 ) haloalkyl ; benzyl optionally substituted with halogen, (C -C.Jalkyl or ( C -C ) haloalkyl ; or phenyl and pyridyl optionally substituted with halogen, ( C 1 -C 3 ) alkyl , ( C _, -C 3 ) haloalkyl or (C 1 -C Jalkoxy ; 11 13 '. and R are independently hydrogen or (C -C. ) alkyl; ! 12 and 1 R are independently ( C -C, ) alkyl , or 1 4 phenyl optionally substituted with halogen, (C 1 -C 3 )alkyl, ( C 1 -C )haloalkyl or (C1.-C4. ) alkoxy ; SUBSTITUTE SHEET R11 and R12 may be taken together as - ( CH ) - , -(CH. ) - or -CH CH.0CH„CH - , each ring optionally substituted with (C -C.Jalkyl, phenyl or benzyl; R 13 and R 14 may be taken together with the carbon to which they are attached to form (C -C β )cycloalkyl; R 15 is (C . -C. Jalkyl or (C. ■ C . Jhaloalkyl; R 16 is hydrogen or ( C -C_ ) alkyl; 17 1 J R is (C 1 -C 6 Jalkyl, ( C 3 -Cg ) alkenyl or ( C 3 -Cg Jalkyπyl; n is 0 , 1 , or 2. 18. A use of claim 17 wherein the plantation crop is selected from citrus, sugarcane, coffee, banana, oil palm, grapes or rubber. 19. A use of Claim 17 or 18 employing at least one of the compounds of the group consisting of 4-[4'- chloro-2'-fluoro-5'-( 1 -methylethoxyJphenyl]- 3,5-dioxo-7-fluoro-1 ,4-diazabicyclo[3.3.0]octane, 4-[4'-chloro-2'-fluoro-5'-(1-methyl-prσp-2- ynyloxy)phenyl]-3 , 5-dioxo-7- luoro- 1 , - diazabicycloC3.3.0]octane, 4-[4'-chloro-2'-fluoro- 5'- (prop-2-ynyloxy) phenyl]-3, 5-dioxo-7- luoro- 1 ,4-diazabicycloC3.3.0]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 , - dihydro-2H-benzoC1 ,4]oxazin-6-yl)-tetrahydro- SUBSTITUTE SHEET pyrroloM ,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- hloro-4- fluoro-5- ( 6-fluoro- 1 ,3-dioxo- tetrahydropyrrolo[1 ,2-c] imidazol-2-yl)phenoxy]but- 2-enoic acid methyl ester (JUPAC) and stereoisomers thereof. 20. A use of claim 17 wherein the plantation crop is peanut and the compound is applied preemergence. SUBSTITUTE SHEET

Inventors: AMUTI KOFI SAM, DRAUZ KARLHEINZ, FEIT DIETER, SCHAEFER MATTHIAS, AMUTI, KOFI, SAM, DRAUZ, KARLHEINZ, FEIT, DIETER, SCHAEFER, MATTHIAS
Applicants: AMUTI KOFI SAM, DEGUSSA, DRAUZ KARLHEINZ, FEIT DIETER, SCHAEFER MATTHIAS, DEGUSSA AKTIENGESELLSCHAFT
Application year: 1993
Main classification: C07D487
IPC codes: A01N43, A01N47, A01N55, A01N57, C07D487, C07F7, C07F9