Herbicides

A thiadiazabicyclooctane or thiadiazabicyclooctene of formula I ##STR716## wherein Z is oxygen or sulfur;

• Q is --C--C--or --C.dbd.C--;
• R is C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 alkynyl, C.sub.3 -C.sub.6 haloalkenyl, C.sub.3 -C.sub.6 haloalkynyl, phenyl, benzyl, phenyl substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkyl or by halogen, benzyl substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkyl or by halogen, it being possible for the unsubstituted and substituted phenyl and benzyl groups to occur in each case only once;
• W is ##STR717## R.sub.1, R.sub.22, R.sub.23, R.sub.24, R.sub.27, R.sub.30, R.sub.33, R.sub.37, R.sub.38 and R.sub.41 are each independently of the others hydrogen or halogen;
• R.sub.2 is hydrogen, cyano, nitro, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkoxy or C.sub.1 -C.sub.4 haloalkyl;
• A is hydrogen, cyano, nitro, COR.sub.3, X.sub.3 R.sub.4, ##STR718## A.sub.1 is cyano or --COR.sub.16 ;
• R.sub.3 is halogen, X.sub.4 -R.sub.5, amino, C.sub.1 -C.sub.4 alkylamino, di-C.sub.1 -C.sub.4 alkylamino, C.sub.2 -C.sub.4 haloalkylamino, di-C.sub.2 -C.sub.4 haloalkylamino, C.sub.1 -C.sub.4 alkoxyalkylamino, di-C.sub.1 -C.sub.4 alkoxyalkylamino, C.sub.3 -C.sub.4 alkenylamino, diallylamino, --N-pyrrolidino, --N-piperidino, --N-morpholino, --N-thiomorpholino, --N-piperidazino, --O--N.dbd.C(CH.sub.3)--CH.sub.3, or --O--CH.sub.2 --CH.sub.2 --O--N.dbd.C(CH.sub.3)--CH.sub.3 ;
• R.sub.4 is hydrogen, C.sub.1 -C.sub.10 alkyl, C.sub.1 -C.sub.4 alkoxy-C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkylthio-C.sub.1 -C.sub.4 alkyl, di-C.sub.1 -C.sub.4 alkylamino-C.sub.1 -C.sub.4 alkyl, halo-C.sub.1 -C.sub.8 alkyl, C.sub.2 -C.sub.8 alkenyl, halo-C.sub.2 -C.sub.8 alkenyl, C.sub.3 -C.sub.8 alkynyl, C.sub.3 -C.sub.7 cycloalkyl, halo-C.sub.3 -C.sub.7 cycloalkyl, C.sub.1 -C.sub.8 alkylcarbonyl, allylcarbonyl, C.sub.3 -C.sub.7 cycloalkylcarbonyl, benzoyl that is unsubstituted or substituted in the phenyl ring by up to three identical or different substituents from the group halogen, C.sub.1 -C.sub.4 alkyl, halo-C.sub.1 -C.sub.4 alkyl, halo-C.sub.1 -C.sub.4 alkoxy and C.sub.1 -C.sub.4 alkoxy;
• or is furanoyl, thienyl;
• or C.sub.1 -C.sub.4 alkyl substituted by phenyl, halophenyl, C.sub.1 -C.sub.4 alkylphenyl, C.sub.1 -C.sub.4 alkoxyphenyl, halo-C.sub.1 -C.sub.4 alkylphenyl, halo-C.sub.1 -C.sub.4 alkoxyphenyl, C.sub.1 -C.sub.6 alkoxycarbonyl, C.sub.1 -C.sub.4 alkoxy-C.sub.1 -C.sub.8 alkoxycarbonyl, C.sub.3 -C.sub.8 alkenyloxycarbonyl, C.sub.3 -C.sub.8 alkynyloxycarbonyl, C.sub.1 -C.sub.8 alkylthiocarbonyl, C.sub.3 -C.sub.8 alkenylthiocarbonyl, C.sub.3 -C.sub.8 alkynylthiocarbonyl, carbamoyl, mono-C.sub.1 -C.sub.4 alkylaminocarbonyl, di-C.sub.1 -C.sub.4 alkylaminocarbonyl;
• or phenylaminocarbonyl that is unsubstituted or substituted in the phenyl ring by up to three identical or different substituents from the group halogen, C.sub.1 -C.sub.4 alkyl, halo-C.sub.1 -C.sub.4 alkyl, halo-C.sub.1 -C.sub.4 alkoxy and C.sub.1 -C.sub.4 alkoxy or that is monosubstituted by cyano or by nitro, or dioxolan-2-yl that is unsubstituted or substituted by one or two C.sub.1 -C.sub.4 alkyl radicals, or dioxan-2-yl that is unsubstituted or substituted by one or two C.sub.1 -C.sub.4 alkyl radicals, or is C.sub.1 -C.sub.4 alkyl substituted by cyano, nitro, carboxy or by C.sub.1 -C.sub.8 alkylthio-C.sub.1 -C.sub.8 alkoxycarbonyl;
• R.sub.5 is hydrogen, C.sub.1 -C.sub.10 alkyl, C.sub.1 -C.sub.4 alkoxy-C.sub.1 -C.sub.4 alkyl, halo-C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.10 alkylthio-C.sub.1 -C.sub.4 alkyl, di-C.sub.1 -C.sub.4 alkylamino-C.sub.1 -C.sub.4 alkyl, cyano-C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.8 alkenyl, halo-C.sub.3 -C.sub.8 alkenyl, C.sub.3 -C.sub.8 alkynyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.3 -C.sub.7 cycloalkyl-C.sub.1 -C.sub.4 alkyl, halo-C.sub.3 -C.sub.7 cycloalkyl, or benzyl that is unsubstituted or substituted in the phenyl ring by up to three identical or different substituents from the group halogen, C.sub.1 -C.sub.4 alkyl, halo-C.sub.1 -C.sub.4 alkyl, halo-C.sub.1 -C.sub.4 alkoxy and C.sub.1 -C.sub.4 alkoxy, or alkali metal ions, alkaline earth metal ions and ammonium ions or the group --[CHR.sub.6 (CH.sub.2).sub.n.sbsb.5 ]--COOR.sub.7 ;
• R.sub.6, R.sub.20, R.sub.21, R.sub.26, R.sub.28, R.sub.32, R.sub.34, R.sub.39, R.sub.40, R.sub.46, R.sub.47, R.sub.49, R.sub.50, R.sub.51 and R.sub.52 are each independently of the others hydrogen or C.sub.1 -C.sub.4 alkyl;
• R.sub.7 and R.sub.48 are each independently of the other hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.8 alkenyl, C.sub.3 -C.sub.8 alkynyl, C.sub.1 -C.sub.8 alkoxy-C.sub.2 -C.sub.8 alkyl, C.sub.1 -C.sub.8 alkylthio-C.sub.1 -C.sub.8 alkyl or C.sub.3 -C.sub.7 cycloalkyl;
• R.sub.8, R.sub.44 and R.sub.45 are each independently of the others hydrogen, C.sub.1 -C.sub.4 alkyl, halo-C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy-C.sub.1 -C.sub.4 alkyl;
• R.sub.9 and R.sub.10 are each independently of the other C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 haloalkyl or C.sub.2 -C.sub.8 alkoxyalkyl, or
• R.sub.9 and R.sub.10 together are an ethano, propano or a cyclohexane-1,2-diyl bridge, those groups being either unsubstituted or substituted by one or two radicals from the group C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl and C.sub.1 -C.sub.4 hydroxyalkyl;
• R.sub.11 is hydrogen, C.sub.1 -C.sub.5 alkyl or C.sub.3 -C.sub.7 alkenyl;
• the radicals R.sub.12 are each independently of the others hydrogen or C.sub.1 -C.sub.8 alkyl;
• R.sub.13 is hydrogen, C.sub.1 -C.sub.5 alkyl, benzyl, halo-C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.8 alkenyl or C.sub.3 -C.sub.8 alkynyl;
• R.sub.14 is C.sub.1 -C.sub.6 alkyl, halo-C.sub.1 -C.sub.5 alkyl or di-C.sub.1 -C.sub.4 alkylamino;
• R.sub.15 is hydrogen, fluorine, chlorine, bromine, C.sub.1 -C.sub.4 alkyl or trifluoromethyl;
• R.sub.16 is chlorine, X.sub.5 -R.sub.17, amino, C.sub.1 -C.sub.4 alkylamino, di-C.sub.1 -C.sub.4 alkylamino, C.sub.2 -C.sub.4 haloalkylamino, di-C.sub.2 -C.sub.4 haloalkylamino, C.sub.1 -C.sub.4 alkoxyalkylamino, di-C.sub.1 -C.sub.4 alkoxyalkylamino, C.sub.3 -C.sub.4 alkenylamino, diallylamino, --N-pyrrolidino, --N-piperidino, --N-morpholino, --N-thiomorpholino, --N-piperidazino, the group --O--N.dbd.C--(CH.sub.3)--CH.sub.3, --O--CH.sub.2 --CH.sub.2 --O--N.dbd.C(CH.sub.3)--CH.sub.3 or the group --N(OR.sub.46)--R.sub.6 ;
• R.sub.17 is hydrogen, C.sub.1 -C.sub.10 alkyl, C.sub.1 -C.sub.4 alkoxy-C.sub.1 -C.sub.4 alkyl, halo-C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.10 alkylthio-C.sub.1 -C.sub.4 alkyl, di-C.sub.1 -C.sub.4 alkylamino-C.sub.1 -C.sub.4 alkyl, cyano-C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.8 alkenyl, halo-C.sub.3 -C.sub.8 alkenyl, C.sub.3 -C.sub.8 alkynyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.3 -C.sub.7 cycloalkyl-C.sub.1 -C.sub.4 alkyl, halo-C.sub.3 -C.sub.7 cycloalkyl, or benzyl that is unsubstituted or substituted in the phenyl ring by up to three identical or different substituents from the group halogen, C.sub.1 -C.sub.4 alkyl, halo-C.sub.1 -C.sub.4 alkyl, halo-C.sub.1 -C.sub.4 alkoxy and C.sub.1 -C.sub.4 alkoxy, or alkali metal ions, alkaline earth metal ions and ammonium ions, the group --[CHR.sub.47 --(CH.sub.2).sub.m ]--COOR.sub.48, or the group [CHR.sub.49 --(CH.sub.2).sub.t --Si(R.sub.8).sub.3 ];
• m is 0, 1, 2, 3 or 4;
• t is 0, 1, 2, 3 or 4;
• R.sub.18 is C.sub.1 -C.sub.4 alkyl;
• R.sub.19 is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.4 alkenyl or C.sub.2 -C.sub.6 alkynyl;
• halo-substituted C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.4 alkenyl or C.sub.3 -C.sub.6 alkynyl;
• C.sub.1 -C.sub.4 alkoxy-C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy-C.sub.1 -C.sub.2 alkoxy-C.sub.1 -C.sub.2 alkyl, 1-phenylpropen-3-yl, cyano- or C.sub.3 -C.sub.6 cycloalkyl-substituted C.sub.1 -C.sub.4 alkyl;
• carboxy-C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.6 alkoxycarbonyl-C.sub.1 -C.sub.4 alkyl, halo-C.sub.1 -C.sub.6 alkoxycarbonyl-C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy-C.sub.1 -C.sub.2 alkoxycarbonyl-C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.6 alkoxycarbonyl-C.sub.1 -C.sub.2 alkoxycarbonyl-C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.6 cycloalkyl-C.sub.1 -C.sub.2 alkoxycarbonyl-C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.5 alkylaminocarbonyl-C.sub.1 -C.sub.4 alkyl, di-C.sub.1 -C.sub.5 alkylaminocarbonyl-C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.1 -C.sub.4 alkylthio-C.sub.1 -C.sub.4 alkyl, benzyl or halo-substituted benzyl, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.3 -C.sub.6 alkenyloxy-C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.8 alkylcarbonyl, ##STR719## C.sub.1 -C.sub.4 alkylthiocarbonyl-C.sub.1 -C.sub.4 alkyl, or the group ##STR720## R.sub.25, R.sub.29, R.sub.31, R.sub.35 and R.sub.36 are each independently of the others hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.8 alkenyl, halo-C.sub.3 -C.sub.8 alkenyl, C.sub.3 -C.sub.8 alkynyl, C.sub.1 -C.sub.4 alkoxy-C.sub.1 -C.sub.8 alkyl, cyano-C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.8 alkoxycarbonyl-C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.3 -C.sub.7 cycloalkyl-C.sub.1 -C.sub.4 alkyl, benzyl, --N-morpholino-, --N-thiomorpholino- or --N-piperidazino-substituted C.sub.1 -C.sub.4 alkyl, di-C.sub.1 -C.sub.4 alkylamino-C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkylaminocarbonyl-C.sub.1 -C.sub.4 alkyl, di-C.sub.1 -C.sub.4 alkylaminocarbonyl-C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxycarbonyl or C.sub.1 -C.sub.4 alkylcarbonyl;
• R.sub.20, R.sub.21, R.sub.26, R.sub.28, R.sub.32, R.sub.34, R.sub.39 and R.sub.40 are each independently of the others hydrogen or C.sub.1 -C.sub.4 alkyl;
• X.sub.1, X.sub.2, X.sub.3, X.sub.4 and X.sub.5 are each independently of the others oxygen or sulfur;
• and n.sub.1, n.sub.2, n.sub.3, n.sub.4 and n.sub.5 are each independently of the others 0, 1, 2, 3 or 4;
• or a salt or complex thereof with an acid, a base or a complexing agent, or a stereoisomer thereof.