Abstract:
Compounds of Formula I are disclosed which are useful for controlling undesired vegetation ##STR1## wherein Q is ##STR2## and W, R A   m , R 4  -R 8  are as defined in the disclosure. Also disclosed are compositions containing the compounds of Formula I and a method for controlling undesired vegetation which involves contacting the vegetation or its environment with an effective amount of a compound of Formula I.

Description:
This application is a Sec. 371 application of PCT application number PCT/EP93/02413, filed 06 Sep. 1993, which is a continuation-in-part of U.S. application Ser. No. 07/942,800, filed 10 Sep. 1992, now abandoned. 
    
    
     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 excel-lent selectivity. 
     The subject of the present invention therefore comprises compounds of formula I ##STR3## 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, CN, OR 3 , (C 1  -C 4 )alkyl, S(O) n  R 3 , COR 3 , C(O)SR 3  and C(O)NR 11  R 12  ; ##STR4## wherein R 3  is (C 1  -C 8 )alkyl, (C 3  -C 8 )cycloalkyl, (C 3  -C 8 )alkenyl, (C 3  -C 8 )alkynyl, (C 1  -C 8 )haloalkyl, (C 2  -C 8 )alkoxyalkyl, (C 2  -C 4 )carboxy alkyl, (C 3  -C 8 )alkoxycarbonylalkyl, (C 4  -C 8 )alkenyloxyalkyl, (C 4  -C 6 )alkynyloxyalky, (C 3  -C 8 )haloalkoxyalkyl, (C 3  -C 8 ) trialkylsilyl, (C 3  -C 8 )cyanoalkyl, (C 3  -C 8 )haloalkenyl, (C 3  -C 8 )haloalkynyl, (C 2  -C 8 )alkylcarbonyl, (C 2  -C 8 )alkoxycarbonyl, (C 2  -C 8 )haloalkoxycarbonyl, P(O)(OR 17 ) 2 , CHR 16  P(O)(OR 17 ) 2  or CHR 16  P(S)(OR 17 ) 2 , phenyl or benzyl optionally substituted with halogen, (C 1  -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 )alkyl, (C 1  -C 2 )haloalkyl, OCH 3 , SCH 3 , OCHF 2 , halogen, CN or NO 2  ; 
     R 6  is hydrogen, (C 1  -C 8 )alkyl, (C 1  -C 8 )haloalkyl. halogen, OR 10 , S(O) n  R 10 , COR 10 , C(O)SR 10 , C(O)NR 11  R 12 , CHO, CH═CHCO 2  R 10 , CO 2  N═CR 13  R 14 , NO 2 , CN, NHSO 2  R 15  or NHSO 2  NHR 15  ; 
     R 7  and R 3  are independently hydrogen, (C 1  -C 3 )alkyl. (C 1  -C 3 )haloalkyl or halogen; when Q is Q-2 or Q-6, R 1  and R 8  together with the carbon to which they are attached may be C═O; 
     R 9  is (C 1  -C 6 )alkyl, (C 1  -C 6 )haloalkyl, (C 2  -C 6 )alkoxyalkyl, (C 3  -C 6 )alkenyl or (C 3  -C 6 )alkynyl; 
     R 10  is (C 1  -C 8 )alkyl. (C 3  -C 8 )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 )alkoxyalkoxyalkyl, (C 4  -C 8 )cycloalkylalkyl, (C 2  -C 4 )carboxyalkyl, (C 3  -C 8 )alkoxycarbonylalkyl, (C 6  -C 8 )alkenyloxycarbonylalkyl, (C 6  -C 8 )alkynyloxycarbonylalkyl, (C 6  -C 8 )cycloalkoxyalkyl, (C 4  -C 8 )alkenyloxyalkyl, (C 4  -C 8 )alkynyloxyalkyl, (C 3  -C 8 )haloalkoxyalkyl, (C 4  -C 8 )haloalkenyloxyalkyl, (C 4  -C 8 )haloalkynyloxyalkyl, (C 6  -C 8 )cycloalkylthioalkyl, (C 4  -C 8 )alkenylthioalkyl, (C 4  -C 8 )alkynylthioalkyl, (C 4  -C 8 )trialkylsilylalkyl, (C 3  -C 8 )cyanoalkyl, (C 3  -C 8 )halocycloalkyl, (C 3  -C 8 )haloalkenyl, (C 5  -C 3 )alkoxyalkenyl, (C 5  -C 8 )haloalkoxyalkenyl, (C 5  -C 8 )alkylthioalkenyl, (C 3  -C 8 )haloalkynyl, (C 5  -C 8 )alkoxyalkynyl, (C 5  -C 8 )haloalkoxyalkynyl, (C 5  -C 8 )alkylthioalkynyl, (C 2  -C 8 )alkylcarbonyl, CHR 16  COR 17 , CHR 16  p(O)(OR 17 ) 2 , P(O)(OR 17 ) 2 , CHR 16  P(S)(OR 17 ) 2 , CHR 16  C(O)NR 11  R 12 , CHR 16  C(O)NH 2 , (C 1  -C 4 )alkyl substituted with phenoxy or benzyloxy optionally substituted with halogen, (C 1  -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  -C 4 )alkoxy; 
     R 11  and R 13  are independently hydrogen or (C 1  -C 4 )alkyl; 
     R 12  and R 14  are independently (C 1  -C 4 )alkyl, or phenyl optionally substituted with halogen, (C 1  -C 3 )alkyl, (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  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 )cycloalkyl; 
     R 15  is (C 1  -C 4 )alkyl or (C 1  -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  -C 6 )alkynyl; 
     W is O or S; 
     n is O or 2; provided that when Q is not fused to a ring bridging the 5&#39;- and 6═-position and C-7 and C-8 are linked by a single bond, then at least one R A  is other than hydroxy, halogen, (C 1  -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&#39;-chloro-2&#39;-fluoro-5&#39;-(prop-2- ynyloxy)phenyl]-3,5-dioxo-7-fluoro-1,4-diazabicyclo-[3.3.0]octane, 4-[4&#39;-chloro-2&#39;-fluoro-5&#39;-(1-methyl-prop-2-ynyloxy)phenyl]-3,5-dioxo-7-fluoro-1,4-diazabicyclo[3.3.0]octane, 4-[4&#39;-chloro-2&#39;-fluoro-5&#39;-(2-propynyloxy)phenyl]-3,5-dioxo-7-chloro-1,4-diazabicyclo[3.3.0]octane, 4-[4&#39;-chloro-2&#39;-fluoro-5&#39;-(1-methyl-ethoxy)phenyl]-3,5-dioxo-7,7-difluoro-1,4-diazabicyclo[3.3.0]octane and stereoisomers thereof. 
     In the above definitions, the term &#34;alkyl&#34;, used either alone or in compound words such as &#34;alkylthio&#34; or &#34;haloalkyl&#34;, 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 &#34;halogen&#34;, either alone or in compound words such as &#34;haloalkyl&#34;, means fluorine, chlorine, bromine or iodine. Further, when used in compound words such as &#34;haloalkyl&#34; said alkyl may be partially or fully substituted with halogen atoms, which may be the same or different. Examples of haloalkyl include CH 2  CH 2  F, CF 2  CF 3  and CH 2  CHFCl. 
     More preferred are compounds of formula I having at least one of the following specifications 
     R 3  is p referred (C 1  -C 4 )alkyl, (C 3  -C 6 )cycloalkyl, (C 3  -C 6 )alkenyl, (C 3  -C 6 )alkynyl, (C 1  -C 4 )haloalkyl, (C 2  -C 6 )alkoxyalkyl: (C 2  -C 4 )carboxyalkyl, (C 3  -C 6 )alkoxycarbonylalkyl, (C 4  -C 6 )alkenyloxyalkyl, (C 1  -C 6 )alkynyloxyalkyl, (C 3  -C 6 )haloalkoxyalkyl, (C 3  -C 6 )trialkylsilyl, (C 3  -C 6 )cyanoalkyl, (C 3  -C 6 )haloalkenyl, (C 3  -C 6 )haloalkynyl, (C 2  -C 6 )alkylcarbonyl, P(O)(OR 17 ) 2 , (C 2  -C 6 )alkoxycarbonyl, (C 2  -C 6 )haloalkoxycarbonyl, CHR 16  P(O)(OR 17 ) 2  or CHR 16  P(S)(OR 17 ) 2 , phenyl or benzyl optionally substituted with halogen, (C 1  -C 3 )alkyl, (C 1  -C 3 )haloalkyl or (C 1  -C 4 )alkoxy; 
     R 5  is halogen or CN; 
     R 6  is hydrogen, (C 1  -C 4 )alkyl, (C 1  -C 4 )haloalkyl, halogen, OR 10 , S(O) n  R 10 , COR 10 , CO 2  R 10 , C(O)SR 10 , C(O)NR 11  R 12 , CH═CHCO 2  R 10 , CO 2  N═CR 13  R 14 , NHSO 2  R 15  or NHSO NHR 15  ; 
     R 7  and R 8  are independently hydrogen, (C 1  -C 3 )alkyl or (C 1  -C 3 )haloalkyl; 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═O; 
     R 9  is (C 1  -C 4 )alkyl, (C 1  -C 4 )haloalkyl, (C 2  -C 4 )alkoxyalkyl, (C 3  -C 6 )alkenyl or (C 3  -C 6 )alkynyl; 
     R 10  is (C 1  -C 4 )alkyl, (C 3  -C 6 )cycloalkyl, (C 3  -C 6 )alkenyl, (C 3  -C 6 )alkynyl, (C 1  -C 4 )haloalkyl, (C 2  -C 4 )alkoxyalkyl, (C 2  -C 4 )alkylthioalkyl, (C 2  -C 4 )alkylsulfinylalkyl, (C 2  -C 4 )alkylsulfonylalkyl, (C 3  -C 6 )alkoxyalkoxyalkyl, (C 4  -C 8 )cycloalkylalkyl, (C 2  -C 4 )carboxyalkyl, (C 3  -C 6 )alkoxycarbonylalkyl, (C 6  -C 8 )alkenyloxycarbonylalkyl, (C 6  -C 8 )alkynyloxycarbonylalkyl, (C 6  -C 8 )cycloalkoxyalkyl, (C 1  -C 6 )alkenyloxyalkyl, (C 4  -C 6 )alkynyloxyalkyl, (C 3  -C 6 )haloalkoxyalkyl, (C 4  -C 8 )haloalkenyloxyalkyl, (C 4  -C 8 )haloalkynyloxyalkyl, (C 6  -C 8 )cycloalkylthioalkyl, (C 4  -C 6 )alkenylthioalkyl, (C 1  -C 6 )alkynylthioalkyl, (C 4  -C 8 )trialkylsilylalkyl, (C 3  -C 4 )cyanoalkyl, (C 3  -C 6 )halocycloalkyl, (C 3  -C 6 )haloalkenyl, (C 5  -C 6 )alkoxyalkenyl, (C 5  -C 6 )haloalkoxyalkenyl, (C 5  -C 6 )alkylthioalkenyl, (C 3  -C 6 )haloalkynyl, (C 5  -C 6 )alkoxyalkynyl, (C 5  -C 6 )haloalkoxyalkynyl, (C 5  -C 6 )alkylthioalkynyl, (C 2  -C 4 )alkyl carbonyl, CHR 16  COR 17 , CHR 16  P(O)(OR 17 ) 2 , P(O)(OR 17 ) 2 , CHR 6  P(S)(OR 17 ) 2 , CHR 16  C(O)NR 11  R 12 , CHR 16  C(O)NH 2 , (C 1  -C 2 )alkyl substituted with phenoxy or benzyloxy optionally substituted with halogen. (C 1  -C 3 )alkyl or (C 1  -C 3 )haloalkyl; benzyl optionally substituted with halogen, (C 1  -C 2 )alkyl or (C 1  -C 2 )haloalkyl; or phenyl and pyridyl optionally substituted with halogen, (C 1  -C 3 )alkyl, (C 1  -C 3 )haloalkyl or (C 1  -C 4 )alkoxy; 
     R 12  and R 14  are independently (C 1  -C 2 )alkyl, phenyl optionally substituted with halogen. (C 1  -C 2 )alkyl, (C 1  -C 2 )haloalkyl or (C 1  -C 2 )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  --, each ring optionally substituted with (C 1  -C 2 )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 6 )cycloalky; 
     R 17  is (C 1  -C 4 )alkyl, (C 3  -C 6 )alkenyl or (C 3  -C 6 )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 ##STR5## in which R 1  is halogen (C 1  -C 4 )alkyl OR 3 , S(O) n  R 3 , COR 3 , CO 2  R 3  C(O)SR 3  C(O)NR 11  R 12  or CN; 
     R 2  is hydrogen, halogen, (C 1  -C 4 )alkyl, OR 3 , S(O) n  R 3 , COR 3 , CO 2  R 3  C(O)SR 3  C(O)NR 11  R 12  or CN; 
     Especially preferred method of use employs compounds of formula II in which at least one of R 1  -R 3  has the meaning 
     R 1  =hydrogen or (C 1  -C 4 )alkyl; 
     R 2  =fluoro, chloro, bromo, OR 3 , S(O) n  R 3 , CO 2  R 3 , C(O)NR 11  R 12  or CN; 
     R 3  =(C 1  -C 4 )alkyl, (C 3  -C 6 )cycloalkyl, (C 3  -C 6 )alkenyl, (C 3  -C 6 )alkynyl, (C 1  -C 4 )haloalkyl or (C 3  -C 6 )trialkylsilyl. 
     Most preferred method of use employ compounds of formula II with at least one of the following specifications 
     R 1  =hydrogen, 
     R 2  =fluoro, chloro, bromo or OR 3 , 
     R 3  =(C 1  -C 2 )alkyl, (C 1  -C 2 )haloalkyl, 
     and in Q 
     R 4  is fluoro or chloro; 
     R 5  is chloro; 
     R 6  is OR 10 , CO 2  R 10 , NHSO 2  R 10  or SR 10  ; 
     R 7  is hydrogen; 
     R 8  is hydrogen or methyl; 
     R 9  is (C 3  -C 4 )alkenyl or (C 3  -C 4 )alkynyl; 
     R 10  is (C 1  -C 4 )alkyl, (C 3  -C 6 )cycloalkyl, (C 3  -C 6 )alkenyl (C 3  -C 4 )alkynyl, (C 1  -C 3 )haloalkyl, (C 2  -C 4 )alkoxyalkyl, (C 3  -C 6 )alkoxycarbonylalkyl, (C 6  -C 8 )alkenyloxycarbonylalkyl, (C 6  -C 8 )alkynyloxycarbonylalkyl or (C 1  -C 2 )carboxyalkyl. 
     If not otherwise specified the invention relates to both the individual possible stereoisomers of formula I and II and also mixtures of the isomers. Stereoisomers exhibiting the 2R-configuration are preferred to others. 
     The 2R-configuration exhibits significantly better control, e.g. up to 8-fold, compared with the 2S-configuration on undesired 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 ##STR6## wherein R═H or (C 1  -C 4 )alkyl, and cyclizing the intermediate and a method for preparing bicyclic imides of formula Ia ##STR7## 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 8-8 positions and is independently selected from the group: hydroxy, halogen, CN, OR 3 , (C 1  -C 4 )alkyl. S(O) n  R 3 , COR 3 , C(O)SR 3  and C(O)NR 11  R 12  ; 
     Q is ##STR8## wherein R 3  is (C 1  -C 8 )alkyl, (C 3  -C 8 )cycloalkyl, (C 3  -C 8 )alkenyl, (C 3  -C 8 )alkynyl, (C 1  -C 8 )haloalkyl, (C 2  -C 8 )alkoxyalkyl, (C 2  -C 4 )carboxyalkyl, (C 3  -C 8 )alkoxycarbonylalkyl, (C 4  -C 8 )alkenyloxyalkyl, (C 4  -C 8 )alkynyloxyalkyl, (C 3  -C 8 )haloalkoxyalkyl, (C 3  -C 8 )trialkylsilyl, (C 3  -C 8 )cyanoalkyl, (C 3  -C 8 )haloalkenyl, (C 3  -C 8 )haloalkynyl, (C 2  -C 8 )alkylcarbonyl, (C 2  -C 8 )alkoxycarbonyl, (C 2  -C 8 )haloalkoxycarbonyl, P(O)(OR 17 ) 2 , CHR 16  P(O)IOR 17 ) 2  or CHR 16  P(S)(OR 17 ) 2 , phenyl or benzyl optionally substituted with halogen, (C 1  -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 )alkyl, (C 1  -C 2 )haloalkyl, OCH 3 , SCH 3 , OCHF 2 , halogen, CN or NO 2  ; 
     R 6  is hydrogen, (C 1  -C 8 )alkyl, (C 1  -C 8 )haloalkyl, halogen, OR 10 , S(O) n  R 10 , COR 10 , C(O)SR 10 , C(O)NR 11  R 12 , CHO, CH═CHCO 2  R 10 , CO 2  N═CR 13  R 14 , NO 2 , CN, NHSO 2  R 15  or NHSO 2  NHR 15  ; 
     R 7  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═O; 
     R 9  is (C 1  -C 8 )alkyl, (C 1  -C 6 )haloalkyl, (C 2  -C 6 )alkoxyalkyl, (C 3  -C 6 )alkenyl or (C 3  -C 6 )alkynyl; 
     R 10  is (C 1  -C 8 )alkyl, (C 3  -C 8 )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 )alkoxyalkoxyalkyl, (C 4  -C 8 )cycloalkylalkyl, (C 2  -C 4 )carboxyalkyl, (C 3  -C 8 )alkoxycarbonylalkyl, (C 6  -C 8 )alkenyloxycarbonylalkyl, (C 6  -C 8 )alkynyloxycarbonylalkyl, (C 6  -C 8 )cycloalkoxyalkyl, (C 4  -C 8 )alkenyloxyalkyl, (C 4  -C 8 )alkynyloxyalkyl, (C 3  -C 8 )haloalkoxyalkyl, (C 4  -C 8 )haloalkenyloxyalkyl, (C 4  -C 8 )haloalkynyloxyalkyl, (C 6  -C 8 )cycloalkylthioalkyl, (C 4  -C 8 )alkenylthioalkyl, (C 4  -C 8 )alkynylthioalkyl, (C 4  -C 8 )trialkylsilylalkyl, (C 3  -C 8 )cyanoalkyl, (C 3  -C 8 )halocycloalkyl, (C 3  -C 8 )haloalkenyl, (C 5  -C 8 )alkoxyalkenyl, (C 5  -C 8 )haloalkoxyalkenyl, (C 5  -C 8 )alkylthioalkenyl, (C 3  -C 8 )haloalkynyl, (C 5  -C 8 )alkoxyalkynyl, (C 5  -C 8 )haloalkoxyalkynyl, (C 5  -C 8 )alkylthioalkynyl, (C 2  -C 8 )alkylcarbonyl, CHR 16  COR 17 , CHR 15  p(O)(OR 17 ) 2 , P(O)(OR 17 ) 2 , CHR 16  P(S)(OR 17 ) 2 , CHR 16  C(O)NR 11  R 12 , CHR 16  C(O)NH 2 , (C 1  -C 4 )alkyl substituted with phenoxy or benzyloxy optionally substituted with halogen, (C 1  -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  -C 4 )alkoxy; 
     R 11  and R 13  are independently hydrogen or (C 1  -C 4 )alkyl; 
     R 12  and R 14  are independently (C 1  -C 4 )alkyl, or phenyl optionally substituted with halogen, (C 1  -C 3 )alkyl, (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  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 art ached to form (C 3  -C 8 )cycloalkyl; 
     R 15  is (C 1  -C 4 )alkyl or (C 1  -C 4 )haloalkyl; 
     R 16  is hydrogen or (C 1  -C 8 )alkyl; 
     R 17  is (C 1  -C 6 )alkyl, (C 3  -C 6 )alkenyl or (C 3  -C 6 )alkynyl; 
     W is O 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 1  -C 4 )alkyl, with phosgene and then with an amine of formula VI 
     
         Q--NH.sub.2                                                VI 
    
     to form compounds of formula VII, ##STR9## and cyclizing the compounds of formula VII, or 
     (c) reacting a compound of formula III with a compound of formula VIII ##STR10## to form a compound of formula IX, ##STR11## 
     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 ##STR12## wherein R 1  is R A   
     R 2  is R A  and H 
     comprising reacting a compound of formula X, ##STR13## 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. 
     Subject of the invention is further a method for making compounds of formula Ia ##STR14## 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, CN, OR 3 , (C 1  -C 4 )alkyl, S(O) n  R 3 , COR 3 , C(O)SR 3  and C(O)NR 11  R 12  ; 
     Q is ##STR15## wherein R 3  is (C 1  -C 8 )alkyl, (C 3  -C 8 )cycloalkyl, (C 3  -C 8 )alkenyl, (C 3  -C 8 )alkynyl, (C 1  -C 8 )haloalkyl, (C 2  -C 8 )alkoxyalkyl, (C 2  -C 4 )carboxyalkyl, (C 3  -C 8 )alkoxycarbonylalkyl, (C 4  -C 8 )alkenyloxyalkyl, (C 4  -C 8 )alkynyloxyalkyl, (C 3  -C 8 )haloalkoxyalkyl, (C 3  -C 8 )trialkylsilyl, (C 3  -C 8 )cyanoalkyl, (C 3  -C 8 )haloalkenyl, (C 3  -C 8 )haloalkynyl, (C 2  -C 8 )alkylcarbonyl, (C 2  -C 8 )alkoxycarbonyl, (C 2  -C 8 )haloalkoxycarbonyl, P(O)(OR 17 ) 2 , CHR 16  P(O)(OR 17 ) 2  or CHR 16  P(S)(OR 17 ) 2 , phenyl or benzyl optionally substituted with halogen, (C 1  -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 )alkyl, (C 1  -C 2 )haloalkyl, OCH 3 , SCH 3 , OCHF 2 , halogen, CN or NO 2  ; 
     R 6  is OR 10 , S(O) n  R 10 , NHSO 2  R 15  or NHSO 2  NHR 15  ; 
     R 7  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═O; 
     R 9  is (C 1  -C 6 )alkyl, (C 1  -C 6 )haloalkyl, (C 2  -C 6 )alkoxyalkyl, (C 3  -C 6 )alkenyl or (C 3  -C 6 )alkynyl; 
     R 10  is (C 1  -C 8 )alkyl, (C 3  -C 8 )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 )alkoxyalkoxyalkyl, (C 4  -C 8 ) cycloalkylalkyl, (C 2  -C 4 )carboxyalkyl, (C 3  -C 8 )alkoxycarbonylalkyl, (C 6  -C 8 )alkenyloxycarbonylalkyl, (C 6  -C 8 )alkynyloxycarbonylalkyl, (C 6  -C 8 )cycloalkoxyalkyl, (C 4  -C 8  )alkenyloxyalkyl, (C 4  -C 8 )alkynyloxyalkyl, (C 3  -C 8 ) haloalkoxyalkyl, (C 4  -C 8 )haloalkenyloxyalkyl, (C 4  -C 8 )haloalkynyloxyalkyl, (C 6  -C 8 )cycloalkylthioalkyl, (C 4  -C 8 )alkenylthioalkyl, (C 4  -C 8 )alkynylthioalkyl, (C 4  -C 8 )trialkylsilylalkyl, (C 3  -C 8 )cyanoalkyl, (C 3  -C 8 )halocycloalkyl, (C 3  -C 8 )haloalkenyl, (C 5  -C 8 )alkoxyalkenyl, (C 5  -C 8 )haloalkoxyalkenyl, (C 5  -C 8 )alkylthioalkenyl, (C 3  -C 8 )haloalkynyl, (C 5  -C 8 )alkoxyalkynyl, (C 5  -C 8 )haloalkoxyalkynyl, (C 5  -C 8 )alkylthioalkynyl, (C 2  -C 8 )alkylcarbonyl, CHR 16  COR 17 , CHR 16  P(O)(OR 17 ) 2 , P(O)(OR 17 ) 2 , CHR 16  P(S)(OR 17 ) 2 , CHR 16  C(O)NR 11  R 12 , CHR 16  C(O)NH 2 , (C 1  -C 4 )alkyl substituted with phenoxy or benzyloxy optionally substituted with halogen, (C 1  -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  -C 4 )alkoxy; 
     R 11  and R 13  are independently hydrogen or (C 1  -C 4 )alkyl; 
     R 12  and R 14  are independently (C 1  -C 4 )alkyl, or phenyl optionally substituted with halogen, (C 1  -C 3 )alkyl, (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  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 )cycloalkyl; 
     R 15  is (C 1  -C 4 )alkyl or (C 1  -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  -C 6 )alkynyl; 
     W is 0 or S; 
     n is 0, 1 or 2: 
     comprising reacting a compound of the formula XlII ##STR16## wherein Y=0, S, NH with a halide selected from the group R 10  --Z, R 15  SO 2  --Z, and R 15  NHSO 2  --Z 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═O                                           III 
    
     in which R 4  to R 17  have the meanings; indicated above, and proline carboxylic acids (esters) of general formula IV ##STR17## in which m and R A  have the meaning Indicated above and R═H or (C 1  -C 4 )alkyl or active ester such as 0-succimid esters or anhydride esters are reacted in accordance with method A, optionally in the presence of an acid acceptor and optionally in the presence of a solvent. 
     A further subject of the invention is a method B for the preparation of compounds of formula I, which is outlined in what follows and m and R A  have the meanings indicated above. Therefor a compound of formula IV, wherein R═H or (C 1  -C 4 )alkyl, is reacted with phosgene or a phosgene substituted [e.g., triphosgene (CCl 3  O) 2  C═O], 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 formula I. ##STR18## 
     A further subject of the invention is method C for the preparation of compounds of formula I, which is outlined in what follows and m and R A  have the meanings indicated above, where a compound of formula III is reacted with a compound of formula VIII, optionally in the presence of an acid acceptor and optionally in the presence of a solvent, to a compound of formula IX, and the compound IX so obtained is then hydrolysed and cyclized to compounds of formula I. ##STR19## 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 1  and R 2  have the meaning indicated above. Therefor a compound of general formula X, wherein R═H or (C 1  -C 4 )alkyl, 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 formula II. ##STR20## 
     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 ##STR21## wherein m, R A , and R 5  have the meaning indicated above and Y=0, S, NH with a halide of the formula XIV, XV or XVI, 
     
         R.sup.10 --Z                                               XIV 
    
     
         R.sup.15 SO.sub.2 --Z                                      XV 
    
     
         R.sup.15 NHSO.sub.2 --Z                                    XVI 
    
     wherein Z is a chlorine-, bromine--or an iodine atom and R 10  and R 15  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, chlorobenzene, a halogenated hydrocarbon such as chloroform, methylene chloride, an ether such as diisopropyl 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 triethylamine or also pyridine (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 triethylamine, and then compounds of formula IlI, dissolved in an inert solvent such as, for example toluene, chlorobenzene or chloroform is added. The reaction mixture is then held advantageously at temperatures between -40° C. to +120° C. preferably -10° C. 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 sulfuric acid. The ureas of formula VII thus formed are then cyclized at temperatures between 50° and 100° C. or, optionally, in 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, &#34;Methoden der organischen Chemie&#34; [Methods of Organic Chemistry], Vol. XV (1974)). 
     In method D, the reaction for R═H and (C 1  -C 4 )alkyl takes place analogous to method A to give compounds formula XII. Known methods (see Houben-Weyl, &#34;Methoden der organischen Chemie&#34; [Methods 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, &#34;Methoden der organisthen Chemie&#34; [Methods 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. 
     Compounds of general formula IV or X are commercially available or prepared according to methods described in the literature (e.g. S. Kanenasa et al., J. Org. Chem. 56, 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 witch 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 herbicidal 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. 
     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 Ia: ##STR22## 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, CN, OR 3 , (C 1  -C 4 )alkyl, S(O) n  R 3 , COR 3 , C(O)SR 3 , and C(O)NR 11  R 12  ; 
     Q is ##STR23## wherein R 3  is (C 1  -C 8 )alkyl, (C 3  -C 8 )cycloalkyl, (C 3  -C 8 )alkenyl, (C 3  -C 8 )alkynyl, (C 1  -C 8 )haloalkyl, (C 2  -C 8 )alkoxyalkyl, (C 2  -C 4 )carboxy alkyl, (C 3  -C 8 )alkoxycarbonylalkyl, (C 4  -C 8 )alkenyloxyalkyl, (C 4  -C 8 )alkynyloxyalkyl, (C 3  -C 8 )haloalkoxyalkyl, (C 3  -C 8 )trialkylsilyl, (C 3  -C 8 )cyanoalkyl, (C 3  -C 8 )haloalkenyl, (C 3  -C 8 )haloalkynyl, (C 2  -C 8 )alkylcarbonyl, (C 2  -C 8 )alkoxycarbonyl, (C 2  -C 8 )haloalkoxycarbonyl, P(O)(OR 17 ) 2 , CHR 16  P(O)(OR 17 ) 2  or CHR 16  P(S)(OR 17 ) 2 , phenyl or benzyl optionally substituted with halogen, (C 1  -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 )alkyl, (C 1  -C 2 )haloalkyl, OCH 3 , SCH 3 , OCHF 2 , halogen, CN or NO 2  ; 
     R 6  is hydrogen, (C 1  -C 8 )alkyl, (C 1  -C 8 )haloalkyl, halogen, OR 10 , S(O) n  R 10 , COR 10 , C(O)SR 10 , C(O)NR 11  R 12 , CHO, CH═CHCO 2  R 10 , CO 2  N═CR 13  R 14 , NO 2 , CN, NHSO 2  R 15  or NHSO 2  NHR 15  ; 
     R 7  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═O; 
     R 9  is (C 1  -C 6 )alkyl, (C 1  -C 6 )haloalkyl, (C 2  -C 6 )alkoxyalkyl, (C 3  -C 6 )alkenyl or (C 3  -C 6 )alkynyl; 
     R 10  is (C 1  -C 8 )alkyl, (C 3  -C 8 )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 )alkoxyalkoxyalkyl, (C 1  -C 8 )cycloalkylalkyl, (C 2  -C 4 )carboxyalkyl, (C 3  -C 8 )alkoxycarbonylalkyl, (C 6  -C 8 )alkenyloxycarbonylalkyl, (C 6  -C 8 )alkynyloxycarbonylalkyl, (C 6  -C 8 )cycloalkoxyalkyl, (C 1  -C 8 )alkenyloxyalkyl, (C 4  -C 8 )alkynyloxyalkyl, (C 3  -C 8 )haloalkoxyalkyl, (C 4  -C 8 )haloalkenyloxyalkyl, (C 4  -C 8 )haloalkynyloxyalkyl, (C 6  -C 8 )cycloalkylthioalkyl, (C 4  -C 8 )alkenylthioalkyl, (C 4  -C 8 )alkynylthioalkyl, (C 4  -C 8 )trialkylsilylalkyl, (C 3  -C 8 )cyanoalkyl, (C 3  -C 8 )halocycloalkyl, (C 3  -C 8 )haloalkenyl, (C 5  -C 8 )alkoxyalkenyl, (C 5  -C 8 )haloalkoxyalkenyl, (C 5  -C 8 )alkylthioalkenyl, (C 3  -C 8 )haloalkynyl, (C 5  -C 8 )alkoxyalkynyl, (C 5  -C 8 )haloalkoxyalkynyl, (C 5  -C 8 )alkylthioalkynyl, (C 2  -C 8 )alkylcarbonyl, CHR 16  COR 17 , CHR 16  P(O)(OR 17 ) 2 , P(O)(OR 17 ) 2 , CHR 16  P(S)(OR 17 ) 2 , CHR 16  C(O)NR 11  IR 12 , CHR 16  C(O)NH 2 , (C 1  -C 4 )alkyl substituted with phenoxy or benzyloxy optionally substituted with halogen, (C 1  -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  -C 4 )alkoxy; 
     R 11  and R 13  are independently hydrogen or (C 1  -C 4 )alkyl; 
     R 12  and R 14  are independently (C 1  -C 4 )alkyl, or phenyl optionally substituted with halogen, (C 1  -C 3 )alkyl, (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  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 )cycloalkyl; 
     R 15  is (C 1  -C 4 )alkyl or (C 1  -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  -C 6 )alkynyl; 
     W is 0 or S; 
     n is 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&#39;-chloro-2&#39;-fluoro-5&#39;-(1-methylethoxy)phenyl]-3,5-dioxo-7-fluoro-1,4-diazabicyclo[3.3.0]octane, 4-[4&#39;-chloro-2&#39;-fluoro-5&#39;-(1-methyl-prop-2-ynyloxy)phenyl]-3,5-dioxo-7-fluoro-1,4-diazabicyclo[3.3.0]octane, 4-[4&#39;-chloro-2&#39;-fluoro-5&#39;-(prop-2-ynyloxy)phenyl]-3,5-dioxo-7-fluoro-1,4-diazabicyclo[3.3.0]octane, 4-[4&#39;-chloro-2&#39;-fluoro-5&#39;-(1-methyl-ethoxy)phenyl]-3,5-dioxo-7,7-difluoro-1,4-diazabicyclo[3.3.0]octane, 2-(7-fluoro-3-oxo-4-prom-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-tetrahydro-pyrrolo[1,2c]imidazole-1,3-dione, 6,6-difluoro-2-(7-fluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1.4]oxazin-6-yl)tetrahydropyrrolo[1,2-c]imidazole-1,3-dione (JUPAC), 4-[2-chloro-4-fluoro-5-(6-fluoro-1,3-dioxotetrahydropyrrolo[1,2-c]imidazol-2-yl)phenoxy]but-2-enoic acid methyl ester (JUPAC) and stereoisomers thereof. Preferred is also a method in which the crop is peanut and the compound is applied preemergence. 
     Chemical examples 
    
    
     EXAMPLE 1 ##STR24## 
     A mixture of 2(R)-Carbomethoxy-4-fluoropyrrolidine (1,47 g, 0,01 ml), triethylamine (50,0 mg, 0,5 mmol) 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% aqueous hydrochloric acid (3×10 ml) and water (3×10 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&#39;-Chloro-2 -fluoro-5&#39;-isopropoxyphenyl)-3,5-dioxo-7-fluoro-1,4-diazabicyclo[3.3.0]octane is obtained in the amount of 2.58 g (75% theoretical) as colourless crystals (m.p. 103°-105° C.). 
     EXAMPLE 2 ##STR25## 
     2R-4-(4&#39;-chloro-2&#39;-fluoro-5&#39;-carboisopropoxy)-3,5-dioxo-7-hydroxy-1,4-diazabicyclo[3.3.0]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&#39;-chloro-2&#39;-fluoro-5&#39;-carboisopropoxy)-7-chloro-3,5-dioxo-1,4-diazabicyclo[3.3.0] octane is obtained in the amount of 3,19 g (82% of theoretical) as a colorless glass. 
     EXAMPLE 3 ##STR26## 
     A mixture or 2R-4-(4-chloro-2-fluoro-5&#39;-carboisopropoxyphenyl)-3,5-dioxo-7-hydroxy-1,4-diazabicyclo[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 (3×15 ml). The collected organic layers are 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&#39;-Chloro-2 -fluoro-.5 -isopropoxyphenyl)-3,5-dioxo-7-methylcarbonyloxy-1,4-diazabicyclo[3.3.0]octane is obtained in the amount of 2.84 g (69% of theoretical) as a colourless glass. 
     EXAMPLE 4 ##STR27## 
     A mixture of 4-(4-(4-Chloro-2&#39;-fluoro-5 -hydroxyphenyl)-3,5-dioxo-7-fluoro-1,4-diazabicyclo[3.3.0]octane (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% aqueous hydrochloric acid, followed by extraction with ether (3×15 ml). The ether layer is dried over sodium sulfate, and filtered. After evaporation of the solvent, the residue is purified by silica gel chromatography. 
     4-(4&#39;-Chloro-2-fluoro-5-propargyloxyphenyl)-3,5-dioxo-7-fluoro-1,4-diazabicyclo[3.3.0] octane is obtained in the amount of 3,16 g (93% of theoretical) in two fractions as, two diastereomers (or diastereomeric mixtures). 
     1. Fraction: m.p. 136°-139° C. [α] D   20  =+45.1° C. 
     2. Fraction: m.p. 143°-145° C. [α] D   20  =-35.2° C. 
     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 lasted in the following tables can be prepared: 
     
                       TABLE 1______________________________________ ##STR28##                              meltingR.sup.A  R.sup.4  R.sup.5                  R.sup.6     point °C.______________________________________H      7-F      Cl     HH      8-F      Cl     HH      7-Cl     Cl     CO.sub.2 CH(CH.sub.3).sub.2H      8-Cl     Cl     OCH(CH.sub.3).sub.2H      6-F      Cl                   ##STR29##H      7-Br     Cl                   ##STR30##______________________________________ 
    
     
                                           TABLE 2__________________________________________________________________________ ##STR31##                         meltingR.sup.1  R.sup.2    R.sup.4      R.sup.5         R.sup.6         point °C.__________________________________________________________________________F      H H Cl HF      H H Br HF      H H CH.sub.3         HF      H F Cl HF      H Cl      Cl HF      H F Cl OCH(CH.sub.3).sub.2                         91-93 (R/S-Mixture                         at Pos. 2 and 7)F      H F Cl OCH(CH.sub.3).sub.2                         103-105 (2R, 7S-Konfi-                         guration, [α].sub.D.sup.20 = +48,8                         (c = 0,5 in CH.sub.2 Cl.sub.2))F      H F Cl OCH(CH.sub.3).sub.2                         glass (2R, 7R-Konfi-                         guration, [Ε].sub.D.sup.20 = +38,3                         (c = 1 in CH.sub.3 OH))F      H F Cl OCH(CH.sub.3).sub.2                         glassF      H F Cl          ##STR32##      143-145 (2S, 7R/S-Konfi-                         guration, [α].sub.D.sup.20 = -35,2                         (c = 0,5 in CH.sub.3 OH))F      H F Cl          ##STR33##      136-139 (2R, 7R/S-Konfi-                         guration, [α].sub.D.sup.20 = +45,1                         (c = 0,5 in CH.sub.2 OH))F      H F Cl          ##STR34##      glass (2R/S, 7R/S-Konfi-                         guration)F      H F Cl          ##STR35##      133-139 (2S, 7R/S-Konfi-                         guration, [α].sub.D.sup.20 = -29,9                         (c = 0,5 in CH.sub.3 OH))F      H F Cl          ##STR36##      121-124 (2R, 7R/S-Konfi-                         guration, [α].sub.D.sup.20 = +41,5                         (c = 0,5 in CH.sub.3 OH))F      H F Cl          ##STR37##      glass (2R/S, 7R/S-Konfi-                         guration)F      H F Cl OCH.sub.3F      H F Cl OCH.sub.2 CH.sub.2 CH.sub.3F      H F Cl OCH.sub.2 CHCH.sub.2F      H F Cl OCH.sub.2 CHCHCO.sub.2 CH.sub.3                         glassF      H F Cl OCH.sub.2 CO.sub.2 CH.sub.3F      H F Cl          ##STR38##F      H F Cl OCH.sub.2 CO.sub.2 C.sub.5 H.sub.11F      H F Cl CNF      H F Cl SCH.sub.3F      H F Cl SCH(CH.sub.3).sub.2F      H F Cl SCH.sub.2 CHCH.sub.2F      H F Cl          ##STR39##F      H F Cl SCH.sub.2 CO.sub.2 HF      H F Cl SCH.sub.2 CO.sub.2 CH.sub.3F      H F Cl          ##STR40##F      H F Cl OC(CH.sub.3)NOCH.sub.3F      H F Cl          ##STR41##F      H F Cl OCHF.sub.2F      H F Cl OCH.sub.2 C(Cl)CH.sub.2F      H F Cl OCF.sub.2 CHFClF      H F Cl NHSO.sub.2 CH.sub.3F      H F Cl NHSO.sub.2 CH(CH.sub.3).sub.2F      H F Cl NHSO.sub.2 NHCH.sub.3F      H F Cl CO.sub.2 CH(CH.sub.3).sub.2                         oil (2R, 7R/S-Konfi-                         guration, [α].sub.D.sup.20 = +32,4                         (c = 0,5 in CH.sub.2 Cl.sub.2))F      H F Cl CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3F      H F Cl CO.sub.2 CH.sub.2 CF.sub.3F      H F Cl CO.sub.2 CH(CH.sub.3).sub.2                         oil (2R/S, 7R/S-Konfi-                         guration)F      H F Cl CO.sub.2 N(CH.sub.3).sub.2F      H F Cl CO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3F      H F Cl CO.sub.2 CH(CH.sub.3)CF.sub.3F      H F Cl          ##STR42##F      H F Cl CO.sub.2 CH(CH.sub.3)CH.sub.2 SCH.sub.3Cl     H F Cl HCl     H F Cl OCHF.sub.2Cl     H F Cl OCH(CH.sub.3).sub.2                         oil (2R, 7S-Konfi-                         guration, [α].sub.D.sup.20 = +41,7                         (c = 0,5 in CH.sub.2 Cl.sub.2))Cl     H F Cl OCF.sub.2 CHFClCl     H F Cl          ##STR43##      oil (2R, 7S-Konfi-                         guration, [α].sub.D.sup.20 = -35,8                         (c = 0,5 in CH.sub.3 OH))Cl     H F Cl          ##STR44##      glass (2R, 7S-Konfi-                         guration)Cl     H F Cl          ##STR45##      glass (2R/S, 7S-Konfi-                         guration)Cl     H F Cl OCH.sub.2 P(O)(C.sub.2 H.sub.5).sub.2Cl     H F Cl          ##STR46##      oil (2R, 7S-Konfi-                         guration)Cl     H F Cl          ##STR47##      130-145 (2S, 7S-Konfi-                         guration, [α].sub.D.sup.20 = -27,3                         in CH.sub.3 OH))Cl     H F Cl OCH.sub.2 C(O)N(CH.sub.3).sub.2Cl     H F Cl O(CH.sub.2).sub.2 OCH.sub.2 CH.sub.3Cl     H F Cl OCH.sub.2 CHNOCH.sub.2 CHCH.sub.2Cl     H F Cl          ##STR48##Cl     H F Cl SCH.sub.2 CO.sub.2 HCl     H F Cl          ##STR49##Cl     H F Cl NHSO.sub.2 CH.sub.3Cl     H F Cl NHSO.sub.2 CF.sub.3Cl     H F Cl CO.sub.2 CH(CH.sub.3).sub.2                         oil (2R, 7S-Konfi-                         guration, [α].sub.D.sup.20 = +36,6                         (c = 0,5 in CH.sub.2 Cl))Cl     H F Cl CO.sub.2 CH(CH.sub.3)CH.sub.2 SCH.sub.3Cl     H F Cl CO.sub.2 CH(CH.sub.3)CF.sub.3Cl     H F Cl CO.sub.2 N(CH.sub.3).sub.2Cl     H F Cl          ##STR50##Cl     H F Cl          ##STR51##Cl     H F Cl CO.sub.2 CH.sub.2 CF.sub.3Cl     H F Cl          ##STR52##Cl     H F Cl CO.sub.2 (CH.sub.2).sub.2 CH.sub.3                         oil (2R, 7S-Konfi-                         guration)Cl     H F Cl CHCHCO.sub.2 CH.sub.2 CH.sub.3OSi(CH.sub.3).sub.3  H F Cl CO.sub.2 CH(CH.sub.3).sub.2                         oil (2R, 7S-Konfi-                         guration, [α].sub.D.sup.20 = +29,5                         (c = 0,5 in CH.sub.2 Cl.sub.2))OSi(CH.sub.3).sub.3  H F Cl          ##STR53##OSi(CH.sub.3).sub.3  H F Cl          ##STR54##OC(O)CH.sub.3  H F Cl CO.sub.2 CH(CH.sub.3).sub.2                         oil (2R, 7S-Konfi-                         guration)OC(O)CH.sub.3  H F Cl CO.sub.2 CH(CH.sub.3).sub.2                         oil (2R, 7R-Konfi-                         guration)OC(O)CH.sub.3  H F Cl          ##STR55##OCO.sub.2 CH.sub.3  H F Cl OCH(CH.sub.3).sub.2                         oil (2R, 7S-Konfi-                         guration)OCO.sub.2 CH.sub.3  H F Cl OCH(CH.sub.3).sub.2                         oil (2R, 7R-Konfi-                         guration)OSO.sub.2 CH.sub.3  H F Cl OCH(CH.sub.3).sub.2                         140-141 (2R, 7R-Konfi-                         guration, [α].sub.D.sup.20 = +56,3                         in CH.sub.2 Cl.sub.2))OCH.sub.3  H F Cl CO.sub.2 CH(CH.sub.3).sub.2                         oil (2R, 7R-Konfi-                         guration, [α].sub.D.sup.20 = +55,1                         (c = 0,5 in CH.sub.2 Cl.sub.2))OCH.sub.3  H F Cl CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3OCH.sub.3  H F Cl OCH(CH.sub.3).sub.2OCH.sub.3  H F Cl          ##STR56##OH     H F Cl OCH(CH.sub.3).sub.2                         63-65 (2R, 7R/S-Konfi-                         guration, [α].sub.D.sup.20 = +47,1                         (c = 0,5 in CH.sub.3 OH))OH     H F Cl CO.sub.2 CH(CH.sub.3).sub.2                         45-48 (2S/7R/S-Konfi-                         guration)OH     H H Cl H               161,5-63OH     H F Cl CO.sub.2 CH(CH.sub.3).sub.2                         110-112 (2R/7R-Konfi-                         guration, [α].sub.D.sup.20 = +39,2                         (c = 0,5 in CH.sub.3 OH)OCH.sub.3  H F Cl          ##STR57## ##STR58##  H F Cl CO.sub.2 CH(CH.sub.3).sub.2CH.sub.3  H F Cl CO.sub.2 CH(CH.sub.3).sub.2CO.sub.2 H  H F Cl OCH(CH.sub.3).sub.2CO.sub.2 H  H F Cl CO.sub.2 CH(CH.sub.3).sub.2Br     H F Cl CO.sub.2 CH(CH.sub.3).sub.2Br     H F Cl CO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3Br     H F Cl OCHF.sub.2Br     H F Cl OCH(CH.sub.3).sub.2                         oil (2R, 7S-Konfi-                         guration, [α].sub.D.sup.20 = +26,5                         (c = 0,5 in CH.sub.2 Cl.sub.2)Br     H F Cl OCF.sub.2 CHF.sub.2Br     H F Cl          ##STR59##Br     H F Cl          ##STR60##Br     H F Cl SCH.sub.2 CO.sub.2 HBr     H F Cl NHSO.sub.2 CH.sub.3Br     H F Cl NHSO.sub.2 CF.sub.3F      F F Cl OCH(CH.sub.3).sub.2                         99-101 (2R-Konfi-                         guration, [α].sub.D.sup.20 = -34,2                         (c = 0,5 in CHCl.sub.3))F      F F Cl OCH.sub.2 CHCH.sub.2                         glassF      F F Cl OCF.sub.2 CHCH.sub.2                         glassF      F F Cl CO.sub.2 CH(CH.sub.3).sub.2F      F F Cl SCH.sub.2 CO.sub.2 CH.sub.3F      F F Cl          ##STR61##F      F F Cl          ##STR62##F      F Cl      Cl CO.sub.2 CH(CH.sub.3).sub.2F      F Cl      Cl          ##STR63##F      F Cl      Cl          ##STR64##__________________________________________________________________________ 
    
     
                                           TABLE 3__________________________________________________________________________ ##STR65##                      meltingR.sup.1 R.sup.2   R.sup.4     R.sup.5          R.sup.7             R.sup.8                    w point °C.__________________________________________________________________________F     H F Cl   H  CH.sub.2                    O glass (2R/S, 7S-Konfi-                      guration)F     H F Cl   H  CH.sub.3                    O glass (2S, 7S-Konfi-                      guration, [α].sub.D.sup.20 = +19,5                      (c = 0,5 in CH.sub.2 Cl.sub.2))F     H F Cl   H  CH.sub.3                    O glass (2R, 7S-Konfi-                      guration, [α].sub.D.sup.20 = -16,6                      (c = 0,5 in CH.sub.2 Cl.sub.2)F     H F Cl   H  H      OF     H F Cl   CH.sub.3             CH.sub.3                    OF     H F Cl   CH.sub.3             CH.sub.2 F                    OF     H F Cl   H  CH.sub.2 CH.sub.3                    OF     H F Cl   H  CH.sub.2 F                    OF     H F Cl   H  CH.sub.2 Cl                    OF     H F Cl   H  CH.sub.2 Br                    OF     H F Br   H  CH.sub.3                    OF     H F CH.sub.3          H  CH.sub.3                    OF     H F OCH.sub.3          H  CH.sub.3                    OF     H F CN   H  CH.sub.3                    OF     H F CF.sub.3          H  CH.sub.3                    OF     F F Cl   H  CH.sub.3                    O 151-154F     F Cl     Cl   H  CH.sub.3                    OF     H F OCF.sub.2 H          H  CH.sub.3                    OF     H Cl     Cl   H  CH.sub.3                    OCl    H F Cl   H  CH.sub.3                    OCl    H Cl     Cl   H  CH.sub.3                    OCl    H F Cl   CH.sub.3             CH.sub.3                    OCl    H F Cl   CH.sub.3             CH.sub.2 F                    OCl    H F Cl   H  CH.sub.2 F                    OCl    H F Cl   H  CH.sub.2 Cl                    OCl    H F Cl   H  CH.sub.2 Br                    OCl    H F Cl   H  CH(CH.sub.3).sub.2                    OCl    H F Cl   H  CH.sub.2 CH.sub.2 Cl                    OCl    H F Cl   H  CH.sub.2 CH.sub.3                    OCl    H F Cl   H  CH.sub.2 (CH.sub.2).sub.2 F                    OCl    H F Br   H  CH.sub.3                    OCl    H F CH.sub.3          H  CH.sub.3                    OCl    H F OCH.sub.3          H  CH.sub.3                    OCl    H F CN   H  CH.sub.3                    OCl    H F CF.sub.3          H  CH.sub.3                    OCl    H F OCF.sub.2 H          H  CH.sub.3                    OOCH.sub.3 H F Cl   H  CH.sub.3                    OOSi(CH.sub.3).sub.3 H F Cl   H  CH.sub.3                    OCH.sub.3 H F Cl   H  CH.sub.3                    OCO.sub.2 H H F Cl   H  CH.sub.3                    OBr    H F Cl   H  CH.sub.3                    OBr    H F Cl   H  CH.sub.2 F                    OBr    H F Cl   H  CH.sub.2 Br                    OBr    H F Cl   CH.sub.3             CH.sub.3                    OBr    H F Cl   CH.sub.3             CH.sub.2 F                    OBr    H Cl     Cl   H  CH.sub.3                    O__________________________________________________________________________ 
    
     
                       TABLE 4______________________________________ ##STR66##                                      meltingR.sup.1 R.sup.2         R.sup.4               R.sup.5                      R.sup.7                          R.sup.8 w   point °C.______________________________________F       H     F     Cl     H   Cl      SF       H     F     Cl     H   CH.sub.3                                  SF       H     F     Cl     H   CH.sub.2 CH.sub.3                                  SF       H     H     SCH.sub.3                      H   H       SF       H     F     Cl     H   Cl      OF       H     F     Cl     H   CH.sub.3                                  OCl      H     F     Cl     H   Cl      SCl      H     F     Cl     H   CH.sub.3                                  SCl      H     F     Cl     H   CH.sub.2 CH.sub.3                                  SCl      H     H     SCH.sub.3                      H   H       SCl      H     F     Cl     H   Cl      OCl      H     F     Cl     H   CH.sub.3                                  OOCH.sub.3   H     F     Cl     H   CH.sub.3                                  SOCH.sub.3   H     F     Cl     H   Cl      SBr      H     F     Cl     H   CH.sub.3                                  SF       F     F     Cl     H   Cl      SBr      H     F     Cl     H   Cl      SBr      H     F     Cl     H   CH.sub.3                                  OOSi(CH.sub.3).sub.3   H     F     Cl     H   CH.sub.3                                  S______________________________________ 
    
     
                       TABLE 5______________________________________ ##STR67##                                  meltingR.sup.1  R.sup.2           R.sup.4                  R.sup.9     w   point °C.______________________________________H        H      F                   ##STR68##  OF        H      F      H           SF        H      F      CH.sub.3    SF        H      F      CH.sub.2 CH.sub.3                              SF        H      F                   ##STR69##  SF        H      F      CH.sub.2 CHCH.sub.2                              SF        H      F      CH.sub.2 OCH.sub.2                              SF        H      F      CH.sub.2 CH.sub.2 CH.sub.3                              SF        H      F                   ##STR70##  SF        H      F      CH(CH.sub.3).sub.2                              SF        H      F      CF.sub.2 CHF.sub.2                              SF        F      F                   ##STR71##  SF        F      F      CH.sub.2 CHCH.sub.2                              SF        F      F      CH.sub.2 CO.sub.2 CH.sub.3                              SF        H      Cl                   ##STR72##  SF        H      F                   ##STR73##  OCl       H      F      H           SCl       H      F      CH.sub.3    SCl       H      F      CH.sub.2 CH.sub.3                              SCl       H      F      CH(CH.sub.3).sub.2                              SCl       H      F      CH.sub.2 CH.sub.2 CH.sub.3                              SCl       H      F                   ##STR74##  SCl       H      F                   ##STR75##  SCl       H      F                   ##STR76##  SCl       H      F      CF.sub.2 CHF.sub.2                              SCl       H      F      CH.sub.2 CHCHCH.sub.3                              SCl       H      Cl                   ##STR77##  SOCH.sub.3    H      F                   ##STR78##  SOCH.sub.3    H      F      CH.sub.3    SBr       H      F                   ##STR79##  SBr       H      F      CH.sub.3    SBr       H      F                   ##STR80##  SBr       H      F      CH.sub.2 CH.sub.3                              SBr       H      F      CH.sub.2 CH.sub.2 CH.sub.3                              SBr       H      Cl                   ##STR81##  SBr       H      F                   ##STR82##  O______________________________________ 
    
     
                                           TABLE 6__________________________________________________________________________ ##STR83##                      meltingR.sup.1 R.sup.2   R.sup.4     R.sup.7        R.sup.8           R.sup.9  w point °C.__________________________________________________________________________F     H F H  H  CH.sub.3 OF     H F H  H  CH.sub.2 CH.sub.3                    OF     H F H  H  CH.sub.2 CH.sub.2 CH.sub.3                    OF     H F H  H  CH(CH.sub.3).sub.2                    OF     H F H  H            ##STR84##                    O 189-191 (2R, 7S-                      Konfiguration)F     H F H  H  CH.sub.2 CCH.sub.2                    OF     H F H  H            ##STR85##                    OF     H F CH.sub.3        H            ##STR86##                    OF     H Cl     H  H            ##STR87##                    OF     H F H  H            ##STR88##                    SOH    H F H  H            ##STR89##                    O 207-209F     H F CH.sub.3        CH.sub.3            ##STR90##                    OCl    H F H  H  H        OCl    H F H  H  CH.sub.3 OCl    H F H  H  CH.sub.2 CH.sub.3                    OCl    H F H  H            ##STR91##                    OCl    H F H  H  CH(CH.sub.3).sub.2                    OCl    H F H  H            ##STR92##                    OCl    H F H  H  CH.sub.2 CHCH.sub.2                    OCl    H F CH.sub.3        H            ##STR93##                    OCl    H F CH.sub.3        CH.sub.3            ##STR94##                    OCl    H Cl     H  H            ##STR95##                    OCl    H F H  H            ##STR96##                    SOCH.sub.3 H F H  H            ##STR97##                    OBr    H F H  H  CH.sub.3 OBr    H F H  H  CH.sub.2 CH.sub.2 CH.sub.3                    OBr    H F CH.sub.3        H            ##STR98##                    OBr    H F CH.sub.3        CH.sub.3            ##STR99##                    OBr    H Cl     H  H            ##STR100##                    OBr    H Cl     H  H            ##STR101##                    SOSi(CH.sub.3).sub.3 H F H  H            ##STR102##                    OOSi(CH.sub.3).sub.3 H F H  H            ##STR103##                    SF     F F H  H            ##STR104##                    O glass (2R-                      Konfigura-                      tion)F     F F H  H  CH.sub.2 CHCH.sub.2                    OF     F F H  H  CH.sub.2 CO.sub.2 CH.sub.3                    O__________________________________________________________________________ 
    
     
                       TABLE 7______________________________________ ##STR105##                               meltingR.sup.1   R.sup.2 R.sup.4 R.sup.7                           R.sup.8                               point °C.______________________________________F         H       H       F     FF         H       F       F     FF         H       F       H     HCl        H       H       F     FCl        H       F       F     FCl        H       F       H     HOCH.sub.3 H       H       F     FOCH.sub.3 H       F       F     FOCH.sub.3 H       F       H     HBr        H       H       F     FBr        H       F       F     FBr        H       F       H     HF         F       F       H     HF         F       F       F     FF         F       H       F     F______________________________________ 
    
     
                       TABLE 8______________________________________ ##STR106##                                    meltingR.sup.1 R.sup.2       R.sup.5             R.sup.6                 R.sup.7       R.sup.8                                    point °C.______________________________________F     H     H     H   CO.sub.2 CH.sub.3                               CH.sub.3Cl    H     H     H   CO.sub.2 CH.sub.3                               CH.sub.3F     H     H     H   CO.sub.2 C.sub.2 H.sub.5                               CH.sub.3F     H     H     H   CO.sub.2 C.sub.2 H.sub.5                               HF     H     H     H   CO.sub.2 (CH.sub.2).sub.2 CH.sub.3                               CH.sub.3Cl    H     H     H   CO.sub.2 (CH.sub.2).sub.2 CH.sub.3                               HCl    H     H     H   CO.sub.2 (CH.sub.2).sub.3 CH.sub.3                               CH.sub.3F     H     H     H   CO.sub.2 (CH.sub.2).sub.3 CH.sub.3                               HF     H     H     H                  ##STR107##   CH.sub.3F     H     H     Cl  CO.sub.2 CH.sub.3                               CH.sub.3F     H     H     Cl  CO.sub.2 C.sub.2 H.sub.5                               CH.sub.3F     H     H     Cl  CO.sub.2 (CH.sub.2).sub.2 CH.sub.3                               CH.sub.3Cl    H     H     Cl  CO.sub.2 (CH.sub.2).sub.3 CH.sub.3                               CH.sub.3F     H     H     Cl                  ##STR108##   CH.sub.3F     H     F     Cl  CO.sub.2 CH.sub.3                               CH.sub.3F     H     F     Cl  CO.sub.2 C.sub.2 H.sub.5                               CH.sub.3F     F     F     Cl  CO.sub.2 CH.sub.3                               CH.sub.3F     F     F     Cl  CO.sub.2 CH.sub.2 CH.sub.3                               CH.sub.3F     F     F     Cl  CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                               CH.sub.3F     F     F     Cl  CO.sub.2 (CH.sub.2).sub.3 CH.sub.3                               CH.sub.3F     F     Cl    Cl  CO.sub.2 (CH.sub.2).sub.3 CH.sub.3                               CH.sub.3F     H     F     Cl  CO.sub.2 (CH.sub.2).sub.2 CH.sub.3                               CH.sub.3F     H     F     Cl  CO.sub.2 (CH.sub.2).sub.2 CH.sub.3                               HF     H     F     Cl                  ##STR109##   CH.sub.3F     H     F     Cl                  ##STR110##   CH.sub.3F     H     F     Cl  CO.sub.2 CHCHCH.sub.2                               CH.sub.3F     H     F     Cl  CO.sub.2 CH(CH.sub.3).sub.2                               CH.sub.3F     H     F     Cl  CO.sub.2 (CH.sub.2).sub.3 CH.sub.3                               CH.sub.3F     H     F     Cl  CO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                               CH.sub.3Cl    H     F     Cl  CO.sub.2 (CH.sub.2).sub.2 CH.sub.3                               CH.sub.3Cl    H     F     Cl  CO.sub.2 (CH.sub.2).sub.3 CH.sub.3                               CH.sub.3Cl    H     F     Cl  CO.sub.2 CH(CH.sub.3).sub.2                               CH.sub.3Br    H     F     Cl  CO.sub.2 (CH.sub.2).sub.2 CH.sub.3                               CH.sub.3Cl    H     F     Cl  CO.sub.2 CH.sub.3                               CH.sub.3Cl    H     F     Cl  CO.sub.2 CH.sub.2 CH.sub.3                               CH.sub.3Br    H     F     Cl  CO.sub.2 (CH.sub.2).sub.3 CH.sub.3                               CH.sub.3Br    H     F     Cl  CO.sub.2 (CH.sub.2).sub.2 CH.sub.3                               HBr    H     F     Cl  CO.sub.2 CH.sub.3                               CH.sub.3OCH.sub.3 H     F     Cl  CO.sub.2 CH.sub.3                               CH.sub.3Br    H     F     Cl  CO.sub.2 CH.sub.2 CH.sub.3                               CH.sub.3OCH.sub.3 H     F     Cl  CO.sub.2 (CH.sub.2).sub.3 CH.sub.3                               CH.sub.3Cl    H     F     Cl                  ##STR111##   CH.sub.3Br    H     F     Cl                  ##STR112##   CH.sub.3Cl    H     F     Cl                  ##STR113##   CH.sub.3Cl    H     F     Cl  CO.sub.2 CH.sub.2 CHCH.sub.2                               CH.sub.3Cl    H     H     H                  ##STR114##   CH.sub.3Cl    H     H     Cl                  ##STR115##   CH.sub.3Br    H     H     Cl                  ##STR116##   CH.sub.3Br    H     F     Cl                  ##STR117##   CH.sub.3OCH.sub.3 H     F     Cl                  ##STR118##   CH.sub.3______________________________________ 
    
     
                       TABLE 9______________________________________ ##STR119##                         meltingR.sup.1R.sup.4      R.sup.5             R.sup.6     point °C.______________________________________CH.sub.3F     Cl     CO.sub.2 CH(CH.sub.3).sub.2                         95-99 [2R-Konfi-                         guration, [α].sub.D.sup.20 = -14,3                         (c = 0,5 in CH.sub.3 OH)]CH.sub.3F     Cl     CO.sub.2 CH(CH.sub.3).sub.2                         97-99 [2S-Konfi-                         guration, [α].sub.D.sup.20 = +13,8                         (c = 0,5 in CH.sub.3 OH)]CH.sub.3F     Cl              ##STR120##CH.sub.3F     Cl              ##STR121##CH.sub.3F     Cl     SCH.sub.2 CO.sub.2 CH.sub.3CH.sub.3F     Cl     OCH.sub.2 CHCH.sub.2______________________________________ 
    
     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      Ingredient               Diluent   Surfactant______________________________________Wettable Powders        25-90       0-74     1-10Oil Suspensions,         5-50      40-95     0-15Emulsions, Solutions,(including Emulsifi-able Concentrates)Dusts         1-25      70-99     0-5Granules, Baits        0.01-99       5-99.99                             0-15and PelletsHigh Strength        90-99       0-10     0-2Compositions______________________________________ 
    
     Typical solid diluents are described in Watkins, et al., &#34;Handbook of Insecticide Dust Diluents and Carriers&#34;, 2nd Ed., Dorland Books:, Caldwell, N.J. Typical liquid diluents and solvents are described in Marsden, &#34;Solvents Guide&#34;, 2nd Ed., Interscience, New York, 1950. &#34;McCutcheon&#39;s Detergents and Emulsifiers Annual&#34;, Allured Publ. Corp., Ridgewood, N.J, as well as Sisely and Wood, &#34;Encyclopedia of Surface Active Agents&#34;, 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., &#34;Pesticide Formulations&#34;, Washington, D.C., 1988, pp 251-259. Suspensions are prepared by wet-milling; see, for 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, &#34;Agglomeration&#34;, Chemical Engineering, Dec. 4, 1967, pp 147-148, &#34;Perry&#39;s Chemical Engineer&#39;s Handbook&#34;, 4th Ed., HcGraw-Hill, New York, 1963, pages 8-57 and following, and WO 91/13546. Pellets can be prepared as described in U.S. Pat. No. 4,172,714. Water-dispersible and water-soluble granules can also be prepared as taught in DE 32 46 493. 
     For further information regarding the art of formulation, see U.S. Pat. No. 3,235,361, Col. 6, line 16 through Col. 7, line 19 and Examples 10-41: U.S. Pat. No. 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. Pat. No. 2,891,855, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4; Klingman, &#34;Weed Control as a Science&#34;, John Wiley and Sons, Inc., New York. 1961, pp 81-96; and Hance et al., &#34;Weed Control Handbook&#34;, 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. 
     EXAMPLE A 
     Wettable Powder 
     
         ______________________________________4-(4&#39;-chloro-2&#39;-fluoro-5&#39;-carboisopropoxyphenyl)-                      80%7-chloro-3,5-dioxo-1,4-diazabicyclo-[3.3.0]octanesodium alkylnaphthalenesulfonate                      2%sodium ligninsulfonate     2%synthetic amorphous silica 3%kaolinite                  13%______________________________________ 
    
     The ingredients are blended, hammer-milled until all the solids are essentially under 50 microns, reblended and packaged. 
     EXAMPLE B 
     Wettable Powder 
     
         ______________________________________4-(4&#39;-chloro-2&#39;-fluoro-5&#39;-carboisopropoxyphenyl)-                      50%7-chloro-3,5-dioxo-1,4-diazabicyclo-[3.3.0]octanesodium alkylnaphthalenesulfonate                      2%low viscosity methyl cellulose                      2%diatomaceous earth         46%______________________________________ 
    
     The ingredients are blended, coarsely hammer-milled and then air-milled to produce Particles essentially all below 10 microns in diameter. The product is reblended before packaging. 
     EXAMPLE C 
     Granule 
     
         ______________________________________Wettable Powder of Example 8                   5%attapulgite granules   95%(U.S.S. 20-40 mesh; 0.84-0.42 mm)______________________________________ 
    
     A slurry of wettable powder containing 25% 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&#39;-chloro-2&#39;-fluoro-5&#39;-carboisopropoxyphenyl)-                      25%7-chloro-3,5-dioxo-1,4-diazabicyclo-[3.3.0]octaneanhydrous sodium sulfate   10%crude calcium ligninsulfonate                       5%sodium alkylnaphthalenesulfonate                       1%calcium/magnesium bentonite                      59%______________________________________ 
    
     The ingredients are blended, hammer-milled and then moistened with about 12% 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 recycled. 
     EXAMPLE 
     Low Strength Granule 
     
         ______________________________________4-(4&#39;-chloro-2&#39;-fluoro-5&#39;-carboisopropoxyphenyl)-                      1%7-chloro-3,5-dioxo-1,4-diazabicyclo-[3.3.0]octaneN,N-dimethylformamide      9%attapulgite granules       90%(U.S.S. 20 to 40 sieve)______________________________________ 
    
     The active ingredient is dissolved in the solvent and the solution is sprayed upon dedusted granules in a double-cone blender. After 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 
     Granule 
     
         ______________________________________4-(4&#39;-chloro-2&#39;-fluoro-5&#39;-carboisopropoxyphenyl)-                      80%7-chloro-3,5-dioxo-1,4-diazabicyclo-[3.3.0]octanewetting agent              1%crude lingninsulfonate salt (containing                      10%5-20% of the natural sugars)attapulgite clay           9%______________________________________ 
    
     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 granulator, the air flow is adjusted 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, optionall with heat, until the water content is reduced to the desired level, generally less than 1%. 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 G 
     Aqueous Suspension 
     
         ______________________________________4-(4&#39;-chloro-2&#39;-fluoro-5&#39;-carboisopropoxyphenyl)-                       40%7-chloro-3,5-dioxo-1,4-diazabicyclo-[3.3.0]octanepolyacrylic acid thickener   0.3%dodecylphenol polyethylene glycol ether                        0.5%disodium phosphate           1%monosodium phosphate         0.5%polyvinyl alcohol            1.0%water                       56.7%______________________________________ 
    
     The ingredients are blended and :ground together in a sand mill to produce particles essentially all under 5 microns in size. 
     EXAMPLE H 
     High Strength Concentrate 
     
         ______________________________________4-(4&#39;-chloro-2&#39;-fluoro-5&#39;-carboisopropoxyphenyl)-                       99%7-chloro-3,5-dioxo-1,4-diazabicyclo-[3.3.0]octanesilica aerogel               0.5%synthetic amorphous silica   0.5%______________________________________ 
    
     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&#39;-chloro-2&#39;-fluoro-5&#39;-carboisopropoxyphenyl)-                       90%7-chloro-3,5-dioxo-1,4-diazabicyclo-[3.3.0]octanedioctyl sodium sulfosuccinate                        0.1%synthetic fine silica        9.9%______________________________________ 
    
     The ingredients are blended and ground in a hammer-mill to produce particles essentially all below 100 microns. The material is sifted through a U.S.S. No. 50 screen (0.3 mm) and then packaged. 
     EXAMPLE J 
     Wettable Powder 
     
         ______________________________________4-(4&#39;-chloro-2&#39;-fluoro-5&#39;-carboisopropoxyphenyl)-                      40%7-chloro-3,5-dioxo-1,4-diazabicyclo-[3.3.0]octanesodium ligninsulfonate     20%montmorillonite clay       40%______________________________________ 
    
     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 K 
     Oil Suspension 
     
         ______________________________________4-(4&#39;-chloro-2&#39;-fluoro-5&#39;-carboisopropoxyphenyl)-                      35%7-chloro-3,5-dioxo-1,4-diazabicyclo-[3.3.0]octaneblend of polyalcohol carboxylic                       6%esters and oil soluble petroleumsulfonatesxylene                     59%______________________________________ 
    
     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. 
     EXAMPLE L 
     Dust 
     
         ______________________________________4-(4&#39;-chloro-2&#39;-fluoro-5&#39;-carboisopropoxyphenyl)-                      10%7-chloro-3,5-dioxo-1,4-diazabicyclo-[3.3.0]octaneattapulgite                10%pyrophyllite               80%______________________________________ 
    
     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-(4&#39;-chloro-2&#39;-fluoro-5&#39;-carboisopropoxyphenyl)-                      25%7-chloro-3,5-dioxo-1,4-diazabicyclo-[3.3.0]octanepolyoxyethylene sorbitol hexaoleate                       5%highly aliphatic hydrocarbon oil                      70%______________________________________ 
    
     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. 
     Utility 
     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 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, sugarcane, 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 triazine, triazole, uracil, urea, amide, carbamate, bipyridylium, phenoxy, sulfonylurea and imidazole 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, buttalin, butylate, cacodylic acid, 2-chloro-N,N-di-2-propenylacetamide, 2-chloroallyl dlethyldithiocarbamate, chloramben, chlorbromuron. chloridazon, chlorimuron ethyl, chlormethoxynil, chlornitrofen, chloroxuron, chlorpropham, chlorsulfuron, chlortoluron, cinmethylin, cinosulfuron, clethodium, clomazone, cloproxydim, clopyralid, calcium salt or methylarsonic acid, cyanazine, cycloate, cyluron, cyperquat, cyprazine, cyprazole, cypromid, dalapon, dazomet, dimethyl 2,3,5,6-tetrachloro-1,4-benzenedicarboxylate, desmedipham, desmetryn, dicamba, dichlobenil, dichlorbrop, diclofop, diethatyl, difenzoquat, diflufenican, dimepiperate, dinitramine, dinoseb, diphenamid, diprobetryn, diquat, diuron, 2-methyl-4,6-dinitrophenol, 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, fluazipop, fluazipop-P, fluchloralin, flumesulam, flumipropyn, fluometuron, fluorochloridone, fuorodifen, fluoroglycofen, flupoxam, fluridone, fluoroxypyr, fluzasulfuron, fomesafen, fosamine, glyphosate, haloxylop, hexaflurate, hexazinone, imazamethabenz, imazapyr, imazaquin, imazamethabenz methyl, imazethapyr, imazosulfuron, ioxynil, isopropalin, isoproturon, isouron, isoxaben, karbutilate, lactofen, lenacil, linuron, metobenzuron, metsulfuron methyl, methylarsonic acid, monoammonium salt of methylarsonic acid, (4-chloro-2-methylphenoxy)acetic acid, S,S&#39;-dimethyl-2-(difluoromethyl)-4-(2-methylpropyl)-6-(trifluoromethyl)-3,5-pyridinedicarbothioate, mecoprop, mefenacet, mefluidide, methalbropalin, methabenzthiazuron, metham, methazole, methoxuron, metolachlor, metribuzin, 1,2-dihydropyridazine-3,6-dione, molinate, monolinuron, monuron, monuron salt and trichloroacetic acid, monosodium salt of methylarsonic acid, nabropamide, naptalam, neburon, nicosulfuron, nitralin, nitrofen, nitrofluorfen, norea, norflurazon, oryzalin, oxadiazon, oxyfluorfen, paraquat, pebulate, pendimethalin, perfluidone, phenmedipham, picloram, 5-[2-chloro-4-(trifluormethyl)phenoxy]-2-nitroacetophenone oxime-0-acetic acid methyl ester, pretilachlor, brimisulfuron, brocyazine, profluralin, prometon, prometryn, pronamide, propachlor, propanil, propazine, propham, prosulfalin, prynachlor, pyrazolate, pyrazon, pyrazosulfuron ethyl, quinchlorac, quizalofop ethyl, rimsulfuron secbumeton, sethoxydim, siduron, simazine, 1-(a,a-dimethylbenzyl)-3-(4-methylphenyl)urea, sulfometuron methyl, trichloroacetic acid, tebuthiuron, terbacil, terbuchlor, terbuthylazine, terbutol, terbutryn, thifensulfuron methyl, thiobencarb, tri-allate, trialkoxydlm, triasulfuron, tribehuron methyl, triclopyr, tridiphane, trifluralin, trimeturon, (2,4-dichlorophenoxy)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: 
     
         ______________________________________Biological Tables______________________________________ ##STR122##               compound 1 ##STR123##               compound 2 ##STR124##               compound 3 ##STR125##               compound 4 ##STR126##               compound 5 ##STR127##               compound 6 ##STR128##               compound 7 ##STR129##               compound 8 ##STR130##               compound 9 ##STR131##               compound 10 ##STR132##               compound 11 ##STR133##               compound 12 ##STR134##               compound 13 ##STR135##               compound 14 ##STR136##               compound 15 ##STR137##               compound 16 ##STR138##               compound 17 ##STR139##               compound 18 ##STR140##               compound 19 ##STR141##               compound 20 ##STR142##               compound 21 ##STR143##               compound 22 ##STR144##               compound 23 ##STR145##               compound 24 ##STR146##               compound 25 ##STR147##               compound 26 ##STR148##               compound 27 ##STR149##               compound 28 ##STR150##               compound 29______________________________________ 
    
     Test procedure 
     Seeds of crabgrass (Digitaria spp.), barnyardgrass (Echinochloa crus-galli), giant foxtail (Setaria faberii), wild oats (Arena fatua), cheatgrass (Bromus secalinus), velvetleaf (Abutilon theophrasti), morningglory (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 2to 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. 
     
                                           TABLE A__________________________________________________________________________postemergence (application rate 2 kg a.i./ha)__________________________________________________________________________   Comp.       Comp.           Comp.               Comp.                   Comp.                       Comp.                           Comp.                               Comp.                                   Comp.                                       Comp.                                           Comp.                                               Comp.   1   2   3   4   5   6   7   8   9   10  11  12__________________________________________________________________________Barnyardgrass   1B  6B  8B  6B  10C 10C 10B 10C 8B  10  10  10Cheat grass   1B  1B  1B  2B  10C 10C 10B 10C 7B  10  10  10Cocklebur   --  4B  --  --  10C 10C --  10C --  10  10  10Morningglory   0.sup.       7B  6B  8B  10C 10C 10B 10C 9B  10  10  10Sorghum 1B  2B  2B  2B  10C 10C  9B 10C 4B  10  10  10Giant foxtail   1B  4B  7B  8B  10C 10C 10B 10C 9B  10  10  10Crabgrass   1B  6B  7B  3B  10C 10C 10B 10C 8B  10  10  10Velvetleaf   0.sup.       5B  8B  7B  10C 10C 10B 10C 8B  10  10  10Wild oats   1B  2B  2B  2B  10C 10C 10B 10C 6B  10  10  10__________________________________________________________________________                               Comp. 13                                    Comp. 14                                         Comp. 15                                              Comp.__________________________________________________________________________                                              16                       Barnyardgrass                               10   10   10   10                       Cheat grass                               10   10   10   10                       Cocklebur                               10   10   10   10                       Morningglory                               10   10   10   10                       Sorghum 10   10   10   10                       Giant foxtail                               10   10   10   10                       Crabgrass                               10   10   10   10                       Velvetleaf                               10   10   10   10                       Wild oats                               10   10   10   10__________________________________________________________________________ 
    
     
                                           TABLE B__________________________________________________________________________preemergence (application rate 2 kg a.i./ha)__________________________________________________________________________   Comp.       Comp.           Comp.               Comp.                   Comp.                       Comp.                           Comp.                               Comp.                                   Comp.                                       Comp.                                           Comp.                                               Comp.   1   2   3   4   5   6   7   8   9   10  11  12__________________________________________________________________________Barnyardgrass   0   8H, 2C           9H, 3C               9H, 3C                   10C 10C 10C 10C 9C, 5H                                       10  10  10Cheat grass   0   0   5H, 1C               6G  10C 10C 10C 10C 3H  10  10  10Cocklebur   --  6H, 2C           --  --  10C 10C 10C 10C 0   10  10  10Morningglory   0   3G, 1C           2G, 1H               0   10C 10C 10C 10C 1C  10  10  10Sorghum 0   3H, 1C           5H, 1C               3G  10C 10C 10C 10C 0   10  10  10Giant foxtail   0   3H  10C 9H, 3C                   10E 10E 10C 10C 10C 10  10  10Crabgrass   0   9H  10C 8H, 1C                   10C 10C 10C 10C 9C  10  10  10Velvetleaf   0   10C 10C 9C  10E 10E 10E 10E 9C  10  10  10Wild oats   0   0   4H, 1C               4G, 2C                   10C 10C 10C 10C 0   10  10  10__________________________________________________________________________                               Comp. 13                                    Comp. 14                                         Comp. 15                                              Comp.__________________________________________________________________________                                              16                       Barnyardgrass                               10   10   10   10                       Cheat grass                               10   10   10   10                       Cocklebur                               10   10   10   10                       Morningglory                               10   10   10   10                       Sorghum 10   10   10   10                       Giant foxtail                               10   10   10   10                       Crabgrass                               10   10   10   10                       Velvetleaf                               10   10   10   10                       Wild oats                               10   10   10   10__________________________________________________________________________ 
    
     
                                           TABLE C__________________________________________________________________________postemergence (application rate 0.2 kg a.i./ha)   Comp.       Comp.           Comp.               Comp.                   Comp.                       Comp.                           Comp.   17  18  19  20  21  22  23__________________________________________________________________________Corn    2B  2B  1B  0   1B  6B  2BWheat   3B  1B  0   0   2B  6B  2BBarnyardgrass   5B  2B  1B  2B  1B  9B  4BCheat grass   3B  2B  0   0   1B  5B  3BCocklebur   2B  5B  0   0   1B  9B  3BMorningglory   5B  6B  2B  1B  1B  10B 6BSorghum --  --  0   0   1B  --  3BGiant foxtail   4B  3B  1B  1B  1B  7B  4BCrabgrass   5B  2B  1B  1B  2Bb 8B  4BVelvetleaf   3B  4B  1B  1B  1B  10B 4BWild oats   2B  1B  0   0   1B  5B  1B__________________________________________________________________________ 
    
     
                                           TABLE D__________________________________________________________________________preemergence (application rate 0.2 kg a.i./ha)   Comp.       Comp.           Comp.               Comp.                   Comp.                       Comp.                           Comp.   17  18  19  20  21  22  23__________________________________________________________________________Corn    0   0   0   0   0   2C  1GWheat   0   0   0   0   0   3C  0Barnyardgrass   0   0   0   0   0   9H, 5C                           1HCheat grass   0   0   0   0   0   5C  0Cocklebur   0   0   0   0   0   7G  0Morningglory   0   0   0   0   0   3H, 2C                           3GSorghum 0   0   0   0   0   5G, 2C                           0Giant foxtail   1H  0   0   2G  0   10H 1HCrabgrass   4G  0   0   2G  0   10H 0Velvetleaf   0   0   0   0   0   9C  0Wild oats   0   0   0   0   0   6C  0__________________________________________________________________________ 
    
     
                       TABLE E.sub.1______________________________________postemergence (rate 200 g/ha)       Comp. Comp.    Comp.   Comp.       26    27       28      29______________________________________Barley        2B      2B       3B     9BBarnyardgrass 4B      1B       2B    10BBedstraw      10B     3B       5B    10BBlackgrass    2B      1B       3B     9BCheatgrass    2B      1B       3B    --Chickweed     6B      3B       --     9BCocklebur     9B      1B       4B    10BCorn          2B      2B       3B     8BCotton        100B    9B       9B    10BCrabgrass     3B      2B       2B    10BDowny brome   --      --       --     9BGiant foxtail 3B      3B       3B     9BLambsquarter  8B      2B       7B    10BMorningglory  10B     2B       5B    10BNutsedge      3B      0.sup.   1B     6BRape          10B     2B       2B    10BRice          5B      3B       3B    10BSorghum       3B      3B       4B    10BSoybean       6B      2B       7B    10BSugar beet    10B     2B       6B    10BVelvetleaf    3B      5G       3B    10BWheat         4B      0.sup.   3B     9BWild buckwheat         10B     1B       6B    10BWild oat      2B      2B       2B    10B______________________________________ 
    
     
                       TABLE E.sub.2______________________________________preemergence (rate 200 g/ha)       Comp.  Comp.    Comp.    Comp.       26     27       28       29______________________________________Barley         0       0         0      5CBarnyardgrass  1H      3G        0     10CBedstraw       9       2G       10C    10CBlackgrass     0       0         1C     9CCheatgrass     8G      0         1C    --Chickweed     10C      0         0     10ECocklebur      0       0         0      7GCorn           0       2G        2G     8HCotton         0       0         0     10CCrabgrass      2H      1H        5G    10CDowny brome   --       --       --     10CGiant foxtail  0       3G        4G    10CLambsquarter  10C      5G       10C    10EMorningglory   0       0         0     10CNutsedge       0       0         0      4CRape           0       1H        2G    10ERice           2G      0         0      7GSorghum        0       0         0      9CSoybean        0       0         0      9HSugar beet     0       1H        9C    10CVelvetleaf    10C      0         0     10CWheat          2C      0         0      7CWild buckwheat         10C      0        10C    10EWild oat       2G      0         0      9C______________________________________ 
    
     
                       TABLE E.sub.3______________________________________postemergence (rate 50 g/ha)       Comp.  Comp.    Comp.    Comp.       26     27       28       29______________________________________Barley         2B      0        1B      9BBarnyardgrass  3B      1B       1B      9BBedstraw       8B      1B       1B     10BBlackgrass     1B      0        1B      7BCheatgrass     1B      1B       1B     --Chickweed      3B      1B       1B      9BCocklebur      7B      1B       1B     10BCorn           2B      1B       1B      8BCotton        10       1B       8B     10BCrabgrass      2B      1B       1B      8BDowny brome   --       --       --      6BGiant foxtail  2B      1B       1B      8BLambsquarter   7B      1B       4B     10BMorningglory   9B      1B       1B     10BNutsedge       1B      0        0       3BRape          10B      0        2B     10BRice           2B      1B       3B      9BSorghum        2B      1B       2B      9HSoybean        8B      1B       3B     10BSugar beet     9B      0        1B     10BVelvetleaf     2B      2B       1B     10BWheat          3B      0        1B      8BWild buckwheat         10B      1B       2B     10BWild oat       2B      0        1B      7B______________________________________ 
    
     
                       TABLE E.sub.4______________________________________preemergence (rate 50 g/ha)       Comp.  Comp.    Comp.    Comp.       26     27       28       29______________________________________Barley         0       0        0       5GBarnyardgrass  0       0        0      10CBedstraw       3G      0        0      10CBlackgrass     0       0        0       9CCheatgrass     0       0        0      --Chickweed      0       0        0      10ECocklebur      0       0        0      --Corn           0       0        0       8HCotton         0       0        0       8HCrabgrass      2H      0        0      10CDowny brome   --       --       --      9CGiant foxtail  0       0        0      10CLambsquarter  10C      --       2G     10EMorningglory   0       0        0       9HNutsedge       0       0        0       6CRape           0       0        0      10ERice           0       0        0       7GSorghum        0       0        0       8HSoybean        0       0        0       9HSugar beet     0       --       0       9CVelvetleaf     2G      0        0      10CWheat          0       0        0       5GWild buckwheat          5G      0        --      9CWild oat       0       0        0       9C______________________________________ 
    
     Test B 
     Plastic tray liners with individual planting compartments were filled with planting medium and seeded separately with dallisgrass (Pasoalum dilatatum), bermudagrass (Cynodon dactylon), annual bluegrass (Poa annum), guineagrass (Panicum maximum), broadleaf signalgrass (Brachiaria platyphylla), goosegrass (Eleusine indicia), large crabgrass (Digitaria sanguinalis), smooth crabgrass (D. ischaemum), sandbur (Cenchrus echinatus), itchgrass (Rottboellia cochinchinensis), Texas panicum (P. texanum), Johnson grass (Sorghum halepense), alfalfa (Medicago sativa), peanut (Arachis hypogea), morningglory (Ipomea sp.), ragweed (Ambrosia elatior), putslane (portulaca oleracea) and Pueraris javanica. Tubers of purple nutsedge (Cyperus rotundus) and yellow nutsedge (C. 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 injuring 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 growth stages. The results are shown in Tables E a  -E 1 . 
     
                       TABLE E.sub.a______________________________________         Compound 4         250       250 g/ha         Preemergence                   Postemergence______________________________________Dallisgrass     0           0Bermudagrass    0           0Annual bluegrass           0           0Guineagrass     0           0Broadleaf signalgrass           0           0Goosegrass      0           0Large crabgrass 0           0Smooth crabgrass           0           0Sandbur         0           0Itchgrass       0           0Johnson grass   0           0Morningglory    0           0Ragweed         0           0Purslane        0           0Alfalfa         0           0Peanut          0           0Purple nutsedge 0           0Yellow nutsedge 0           0______________________________________ 
    
     
                       TABLE E.sub.b______________________________________      Compound 6      500  250    125    500  250  125 g/ha      Preemergence                 Postemergence______________________________________Dallisgrass  100    100    100  100  100  100Bermudagrass 100    100    100  70   100  70Annual bluegrass        100    100    100  50   50   50Guineagrass  100    100    100  80   50   40Broadleaf signalgrass        100    100    90   50   60   60Goosegrass   100    100    100  100  90   90Large crabgrass        100    100    100  100  90   90Smooth crabgrass        100    100    100  90   60   50Sandbur      100    100    100  100  90   70Itchgrass    100    100    80   70   50   30Texas panicum        100    100    100  100  80   50Johnson grass        100    100    80   30   30   20Morningglory 100    100    90   100  100  100Purslane     100    100    100  100  100  100Alfalfa      100    100    100  100  100  100Peanut       0      0      0    70   30   20______________________________________ 
    
     
                       TABLE E.sub.c______________________________________         Compound 6         250       250 g/ha         Preemergence                   Postemergence______________________________________Dallisgrass     100         90Bermudagrass    100         40Annual bluegrass           100         20Guineagrass     100         60Broadleaf signalgrass           100         30Goosegrass      100         80Large crabgrass 100         90Smooth crabgrass           100         50Sandbur          90         100Itchgrass       100         20Johnson grass   100         20Morningglory    100         100Ragweed         100         100Purslane        100         80Alfalfa         100         100Peanut           0          30______________________________________ 
    
     
                       TABLE E.sub.d______________________________________         Compound 6         250       250 g/ha         Preemergence                   Postemergence______________________________________Dallisgrass     100         90Bermudagrass    100         50Annual bluegrass           100         70Guineagrass     100         30Broadleaf signalgrass           100         30Goosegrass      100         80Large crabgrass 100         70Smooth crabgrass           100         50Sandbur         100         60Itchgrass       100         30Johnson grass   100         20Morningglory     80         100Ragweed         100         100Purslane        100         90Alfalfa         100         100Peanut           0          70Purple nutsedge  40         20Yellow nutsedge  80         80______________________________________ 
    
     
                       TABLE E.sub.e______________________________________         Compound 7         250       250 g/ha         Preemergence                   Postemergence______________________________________Dallisgrass     100         20Bermudagrass    100          0Annual bluegrass            80         90Guineagrass     100          0Broadleaf signalgrass           100          0Goosegrass      100          0Large crabgrass 100          0Smooth crabgrass           100          0Sandbur          90          0Itchgrass        70          0Johnson grass    60          0Morningglory     80         100Ragweed         100         100Purslane        100         100Alfalfa          90         100Peanut           20         60Purple nutsedge  0          20Yellow nutsedge  10         50______________________________________ 
    
     
                       TABLE E.sub.f______________________________________         Compound 11         250       250 g/ha         Preemergence                   Postemergence______________________________________Dallisgrass     100         100Bermudagrass    100         80Annual bluegrass           100         60Guineagrass     100         70Broadleaf signalgrass           100         80Goosegrass      100         80Large crabgrass 100         80Smooth crabgrass           100         60Sandbur         100         80Itchgrass       100         100Johnson grass   100         100Morningglory    100         100Ragweed         100         100Purslane        100         90Alfalfa         100         100Peanut           60         100Purple nutsedge  20         30Yellow nutsedge  80         100______________________________________ 
    
     
                       TABLE E.sub.g______________________________________         Compound 12         250       250 g/ha         Preemergence                   Postemergence______________________________________Dallisgrass     90          20Bermudagrass    20          0Annual bluegrass            0          0Guineagrass     80          0Broadleaf signalgrass            0          0Goosegrass      100         0Large crabgrass 90          0Smooth crabgrass           50          0Sandbur         60          0Itchgrass       20          0Johnson grass   80          0Morningglory    50          20Ragweed         30          20Purslane        100         20Alfalfa         90          0Peanut          20          0Purple nutsedge  0          0Yellow nutsedge  0          0______________________________________ 
    
     
                       TABLE E.sub.h______________________________________         Compound 13         250       250 g/ha         Preemergence                   Postemergence______________________________________Dallisgrass     100         0Bermudagrass    30          0Annual bluegrass           30          0Guineagrass     90          0Broadleaf signalgrass           20          0Goosegrass      100         0Large crabgrass 70          0Smooth crabgrass           90          0Sandbur         30          0Itchgrass       20          0Johnson grass   80          0Morningglory    40          0Ragweed         70          0Purslane        100         30Alfalfa         40          0Peanut           0          0Purple nutsedge  0          0Yellow nutsedge  0          0______________________________________ 
    
     
                       TABLE E.sub.i______________________________________         Compound 14         250       250 g/ha         Preemergence                   Postemergence______________________________________Dallisgrass     100         100Bermudagrass    100         60Annual bluegrass           100         70Guineagrass     100         70Broadleaf signalgrass           100         60Goosegrass      100         80Large crabgrass 100         70Smooth crabgrass           100         50Sandbur         100         100Itchgrass       100         70Johnson grass   100         50Morningglory    100         100Ragweed         100         100Purslane        100         90Alfalfa         100         100Peanut           50         100Purple nutsedge  40         50Yellow nutsedge  80         100______________________________________ 
    
     
                       TABLE E.sub.j______________________________________         Compound 22         250       250 g/ha         Preemergence                   Postemergence______________________________________Dallisgrass     90          0Bermudagrass    90          0Annual bluegrass           70          0Guineagrass     100         0Broadleaf signalgrass           90          0Goosegrass      100         0Large crabgrass 100         0Smooth crabgrass           90          0Sandbur         90          0Itchgrass       100         0Johnson grass   50          0Morningglory    80          60Ragweed         100         70Purslane        100         90Alfalfa         60          90Peanut          20          30Purple nutsedge  0          0Yellow nutsedge  0          0______________________________________ 
    
     
                       TABLE E.sub.k______________________________________         Compound 24         250       250 g/ha         Preemergence                   Postemergence______________________________________Dallisgrass     100         90Bermudagrass    100         50Annual bluegrass           100         50Guineagrass     100         70Broadleaf signalgrass           100         30Goosegrass      100         80Large crabgrass 100         60Smooth crabgrass           100         50Sandbur         100         80Itchgrass       100         50Johnson grass   100         50Morningglory    100         100Ragweed         100         100Purslane        100         90Alfalfa         100         100Peanut           60         100Purple nutsedge  60         20Yellow nutsedge  70         100______________________________________ 
    
     
                       TABLE E.sub.l______________________________________         Compound 25         250       250 g/ha         Preemergence                   Postemergence______________________________________Dallisgrass     100         100Bermudagrass    100         20Annual bluegrass           100          0Guineagrass     100         40Broadleaf signalgrass           100         40Goosegrass      100         30Large crabgrass 100         50Smooth crabgrass           100         20Sandbur         100         20Itchgrass       100         60Johnson grass   100         20Morningglory    100         80Ragweed         100         100Purslane        100         90Alfalfa         100         100Peanut           60         70Purple nutsedge  0          20Yellow nutsedge  60         30______________________________________ 
    
     Test C 
     Windowsill flats were filled with planting medium and seeded with peanut (A. hypogea), gaint foxtail (Setari faberi), large crabgrass (D. Sanguinalis), guineagrass (P. maximum), Johnson grass (S. haliebense), nightshade (solanum nigrum), morningglory (Ipomes sp.) and velvetleaf (Abutilon theophrasti). The plantings were treated preemergence with Compound 6 formulated in a non-phytotoxic spray solution. Planets 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 mays), soybean (Glycine max.), peanut (A. hypogea), tomato (Lycopersium esenlentum), gaint foxtail (S. faberi), guineagrass (P. maximum), Johnson grass (S. halepense), velvetleaf (A. theophrasti), morningglory, nightshade varieties--Solanum nigrum, S. nigrum subsp. nigrum. S. ptycanthus (green berries and black berries), S. nigrum subsp. schetesii and S. nigrum (atrazine tolerant). 
     The plantings were treated preemergence with Compound 6 formulated in a non-phytotoxic spray solution. Plants were visually rated at the enid of the test and compared with the appropriate controls. The injury ratings used in Test 8 were also employed in this test. The results are shown in Table G. 
     Test 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 viridus) and guineagrass (P. 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. 
     
                       TABLE F______________________________________       Compound 6       250  125        64     g/haSpecies       Preemergence______________________________________       21 DATPeanut         60     20        0Giant foxtail 100    100        100Large crabgrass         100    100        100Guineagrass   100    100        100Johnson grass 100    100        100Nightshade    100    100        100Morningglory  100    100        80Velvetleaf    100    100        100       40 DATPeanut         40     20        0Giant foxtail 100    100        100Large crabgrass         100    100        100Guineagrass   100    100        100Johnson grass 100    100        90Nightshade    100    100        100Morningglory  100    100        80Velvetleaf    100    100        100______________________________________ 
    
     
                       TABLE G______________________________________        Compound 6        64   32     16     8    4    g/haSpecies        Preemergence______________________________________Corn           60     60     10   0    0Soybean        70     40     0    0    0Peanut         20     0      0    0    0Tomato         100    100    100  100  90Giant foxtail  100    100    100  90   40Guineagrass    100    100    80   80   60Johnson rass   100    90     30   20   20Velvetleaf     100    100    100  100  100Morningglory   50     30     20   0    0Solanum nigrum 100    100    100  100  100S. nigrum      100    100    100  100  100S. nigrum subsp. nigrum          100    100    100  100  100S. ptycanthus (green          100    100    100  100  100berries)S. nigrum subsp. schetesii          100    100    100  100  100S. ptycanthus (black          100    100    100  100  100berries)S. nigrum (atrazine          100    100    100  100  100tolerant)______________________________________ 
    
     
                       TABLE H______________________________________         Compound 6         500  250    125    64   g a.i./ha______________________________________         21 DATPost directed   0      0      0    0Citrus (rough lemon)PreemergenceBalsam apple vine           100    100    100  100Sandbur         100    100    100  100Pigweed         100    100    100  100Guineagrass     100    100    100  100Postemergence   100    100    100  100Balsam apple vine         65 DATPost directed   0      0      0    0Citrus (rough lemon)PreemergenceBalsam apple vine           100    100    100  100Sandbur         100    100    100  100Pigweed         100    100    100  100Guineagrass     100    100    100  100Postemergence   100    100    100  100Balsam apple vine______________________________________