HERBICIDAL MALONAMIDES
20240365783 ยท 2024-11-07
Inventors
- Markus Kordes (Ludwigshafen, DE)
- Marc Heinrich (Ludwigshafen, DE)
- Gunther Zimmermann (Ludwigshafen, DE)
- Tobias Seiser (Ludwigshafen, DE)
- Gerd Kraemer (Limburgerhof, DE)
- Trevor William Newton (Limburgerhof, DE)
Cpc classification
C07C233/54
CHEMISTRY; METALLURGY
International classification
Abstract
The present invention relates to malonamide compounds of the formula (I) where the variables are as defined in the claims and the description, and to compositions comprising these compounds. The invention also relates to the use of said malonamide compounds or the corresponding compositions for controlling unwanted vegetation, and to methods of applying the malonamide compounds or the corresponding compositions.
##STR00001##
Claims
1. A compound of formula (I) ##STR00113## wherein the substituents have the following meanings: R.sup.1 is hydrogen, (C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-haloalkyl, (C.sub.3-C.sub.4)-cycloalkyl, (C.sub.2-C.sub.3)-alkenyl, (C.sub.2-C.sub.3)-haloalkenyl, (C.sub.2-C.sub.3)-alkynyl, (C.sub.2-C.sub.3)-haloalkynyl, (C.sub.1-C.sub.3)-alkoxy-(C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-alkoxy, (C.sub.1-C.sub.3)-haloalkoxy, or (C.sub.1-C.sub.3)-alkoxy-(C.sub.1-C.sub.3)-alkoxy; R.sup.2 is hydrogen, halogen, hydroxyl, cyano, (C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-haloalkyl, (C.sub.1-C.sub.3)-alkoxy, or (C.sub.1-C.sub.3)-haloalkoxy; R.sup.3 is hydrogen, halogen, nitro, hydroxyl, cyano, (C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-haloalkyl, hydroxy-(C.sub.1-C.sub.3)-alkyl, (C.sub.3-C.sub.5)-cycloalkyl, (C.sub.3-C.sub.5)-halocycloalkyl, hydroxy-(C.sub.3-C.sub.5)-cycloalkyl, (C.sub.2-C.sub.3)-alkenyl, (C.sub.2-C.sub.3)-haloalkenyl, (C.sub.2-C.sub.3)-alkynyl, (C.sub.2-C.sub.3)-haloalkynyl, (C.sub.1-C.sub.3)-alkoxy, (C.sub.1-C.sub.3)-haloalkoxy, (C.sub.1-C.sub.3)-alkoxycarbonyl, (C.sub.1-C.sub.3)-haloalkoxycarbonyl, (C.sub.1-C.sub.3)-alkylthio, (C.sub.1-C.sub.3)-haloalkylthio, (C.sub.1-C.sub.3)-alkylsulfinyl, (C.sub.1-C.sub.3)-haloalkylsulfinyl, (C.sub.1-C.sub.3)-alkylsulfonyl, or (C.sub.1-C.sub.3)-haloalkylsulfonyl; R.sup.4 is hydrogen, halogen, hydroxyl, cyano, (C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-haloalkyl, (C.sub.3-C.sub.4)-cycloalkyl, (C.sub.3-C.sub.4)-halocycloalkyl, (C.sub.1-C.sub.3)-alkoxy, (C.sub.1-C.sub.3)-haloalkoxy, (C.sub.2-C.sub.3)-alkenyl, (C.sub.2-C.sub.3)-haloalkenyl, (C.sub.2-C.sub.3)-alkynyl, (C.sub.2-C.sub.3)-haloalkynyl, or (C.sub.1-C.sub.3)-alkylthio; R.sup.5 is hydrogen, halogen, nitro, hydroxyl, cyano, (C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-haloalkyl, hydroxy-(C.sub.1-C.sub.3)-alkyl, (C.sub.3-C.sub.5)-cycloalkyl, (C.sub.3-C.sub.5)-halocycloalkyl, hydroxy-(C.sub.3-C.sub.5)-cycloalkyl, (C.sub.2-C.sub.3)-alkenyl, (C.sub.2-C.sub.3)-haloalkenyl, (C.sub.2-C.sub.3)-alkynyl, (C.sub.2-C.sub.3)-haloalkynyl, (C.sub.1-C.sub.3)-alkoxy, (C.sub.1-C.sub.3)-haloalkoxy, (C.sub.1-C.sub.3)-alkoxycarbonyl, (C.sub.1-C.sub.3)-haloalkoxycarbonyl, (C.sub.1-C.sub.3)-alkylthio, (C.sub.1-C.sub.3)-haloalkylthio, (C.sub.1-C.sub.3)-alkylsulfinyl, (C.sub.1-C.sub.3)-haloalkylsulfinyl, (C.sub.1-C.sub.3)-alkylsulfonyl, or (C.sub.1-C.sub.3)-haloalkylsulfonyl; R.sup.6 is hydrogen, halogen, hydroxyl, cyano, (C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-haloalkyl, (C.sub.1-C.sub.3)-alkoxy, or (C.sub.1-C.sub.3)-haloalkoxy; R.sup.7 and R.sup.8, independently of each other, are (C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.2-C.sub.6)-alkenyl or (C.sub.2-C.sub.6)-alkynyl, where the four last-mention aliphatic and cycloaliphatic radicals are each substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl, and cyano; R.sup.9 is hydrogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.3-C.sub.4)-cycloalkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-haloalkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.2-C.sub.6)-haloalkynyl, (C.sub.1-C.sub.3)-alkoxy-(C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-haloalkoxy, or (C.sub.1-C.sub.3)-alkoxy-(C.sub.1-C.sub.3)-alkoxy; X is a bond (X.sup.0) or a divalent unit selected from the group consisting of (X.sup.1), (X.sup.2), (X.sup.3), (X.sup.4), (X.sup.5), and (X.sup.6): ##STR00114## R.sup.10 and R.sup.11, independently of each other and independently of each occurrence, are hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, CO.sub.2R.sup.e, CONR.sup.bR.sup.d, NR.sup.bCO.sub.2R.sup.e, R.sup.a, (C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.5)-cycloalkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, where the four last-mentioned aliphatic and cycloaliphatic radicals are each substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl, and cyano; (C.sub.1-C.sub.6)-alkoxy, (C.sub.3-C.sub.6)-cycloalkoxy, (C.sub.2-C.sub.6)-alkenyloxy, (C.sub.2-C.sub.6)-alkynyloxy, (C.sub.1-C.sub.3)-alkylthio, (C.sub.1-C.sub.3)-alkylsulfinyl, or (C.sub.1-C.sub.3)-alkylsulfonyl, where aliphatic or cycloaliphatic moieties of the seven last-mentioned radicals are each substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, and (C.sub.1-C.sub.2)-alkoxy; R.sup.12 to R.sup.15, independently of each other and independently of each occurrence, are hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, CO.sub.2R.sup.e, CONR.sup.bR.sup.d, NR.sup.bCO.sub.2R.sup.e, R.sup.a, (C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.5)-cycloalkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, phenyl, imidazolyl, where the six last-mentioned aliphatic, cycloaliphatic, aromatic and heteroaromatic radicals are each substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl, and cyano; (C.sub.1-C.sub.6)-alkoxy, (C.sub.3-C.sub.6)-cycloalkoxy, (C.sub.2-C.sub.6)-alkenyloxy, (C.sub.2-C.sub.6)-alkynyloxy, (C.sub.1-C.sub.3)-alkylthio, (C.sub.1-C.sub.3)-alkylsulfinyl, or (C.sub.1-C.sub.3)-alkylsulfonyl, where aliphatic or cycloaliphatic moieties of the seven last-mentioned radicals are each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, cyano, and (C.sub.1-C.sub.2)-alkoxy; Y is Z, or is (C.sub.1-C.sub.12)-alkyl, (C.sub.3-C.sub.5)-cycloalkyl, (C.sub.2-C.sub.12)-alkenyl or (C.sub.2-C.sub.12)-alkynyl, where the four last-mentioned aliphatic and cycloaliphatic radicals are each substituted by m radicals selected from the group consisting of R.sup.b, R.sup.c, R.sup.e, and R; and are further substituted by p radicals selected from the group consisting of CO.sub.2R.sup.e, CONR.sup.bR.sup.h, S(O),R.sup.a, S(O).sub.2NR.sup.bR.sup.d, SO.sub.2NR.sup.bCOR.sup.e, COR.sup.b, CONR.sup.eS(O)R.sup.a, CONR.sup.eS(O).sub.2R.sup.e, CONR.sup.b1S(O).sub.2NR.sup.b2R.sup.b3, NR.sup.bR.sup.e, NR.sup.bCOR.sup.e, NR.sup.bCONR.sup.eR.sup.e, NR.sup.bCO.sub.2R.sup.e, NR.sup.bSO.sub.2R.sup.e, NR.sup.b1S(O).sub.2NR.sup.b2R.sup.b3 OC(O) NR.sup.bR.sup.e, OC(S) NR.sup.bR.sup.e, POR.sup.lR.sup.l, and C(R.sup.b)NOR.sup.e; Z is a three-, four-, five-, or six-membered saturated, partly unsaturated, fully unsaturated or aromatic ring, except phenyl, which is formed from r carbon atoms, n nitrogen atoms, n sulfur atoms, and n oxygen atoms, and which is substituted by m radicals selected from the group consisting of R.sup.b, R.sup.c, R.sup.e, and R and p radicals from the group consisting of CO.sub.2R.sup.e, CONR.sup.bR.sup.h, S(O),R.sup.a, SO.sub.2NR.sup.bR.sup.d, SO.sub.2NR.sup.bCOR.sup.e, CORD, CONR.sup.eS(O)R.sup.a, CONR.sup.eSO.sub.2R.sup.a, CONR.sup.b1SO.sub.2NR.sup.b2R.sup.b3, NR.sup.bR.sup.e, NR.sup.bCOR.sup.e, NR.sup.bCONR.sup.eR.sup.e, NR.sup.bCO.sub.2R.sup.e, NR.sup.bSO.sub.2R.sup.e, NR.sup.b1SO.sub.2NR.sup.b2R.sup.b3, OCONR.sup.bR.sup.e, OCSNR.sup.bR.sup.e, POR.sup.lR.sup.l, and C(R.sup.b)NOR.sup.e, and where the sulfur and carbon ring atoms bear n oxo groups; each R.sup.a is independently (C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.4)-alkynyl, or (C.sub.3-C.sub.6)-cycloalkyl, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxy, and (C.sub.1-C.sub.3)-alkoxy; R.sup.b, R.sup.b1, and R.sup.b2, independently of each other and independently of each occurrence, are hydrogen or have one of the meanings given for R.sup.a; each R.sup.b3 has independently one of the meanings given for R.sup.d; or R.sup.b2 and R.sup.b3, together with the nitrogen atom they are bound to, form a saturated 3-, 4-, 5-, 6-, or 7-membered N-bound heterocyclic ring which optionally contain one further heteroatom or heteroatom group selected from the group consisting of N, O, S, S(O), and S(O).sub.2 as ring member; each R.sup.e is independently fluorine, chlorine, bromine, iodine, cyano, hydroxyl, S(O).sub.nR.sup.a, or (C.sub.1-C.sub.6)-alkoxy, (C.sub.2-C.sub.6)-alkenyloxy or (C.sub.2-C.sub.6)-alkynyloxy, where aliphatic or cycloaliphatic moieties of the three lastmentioned radicals are each substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano, and (C.sub.1-C.sub.2)-alkoxy; each R.sup.d is independently hydrogen or (C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.4)-alkenyl, (C.sub.2-C.sub.4)-alkynyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.3)-alkyl, phenyl-(C.sub.1-C.sub.3)-alkyl, or furanyl-(C.sub.1-C.sub.3)-alkyl, where each of the seven lastmentioned radicals is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano, CO.sub.2R.sup.a, CONR.sup.bR.sup.h, (C.sub.1-C.sub.2)-alkoxy, (C.sub.1-C.sub.3)-alkylthio, (C.sub.1-C.sub.3)-alkylsulfinyl, (C.sub.1-C.sub.3)-alkylsulfonyl, phenylthio, phenylsulfinyl, and phenylsulfonyl; each R.sup.e has independently one of the meanings given for R.sup.d; each R is independently (C.sub.1-C.sub.3)-alkyl or (C.sub.1-C.sub.3)-alkoxy; each R.sup.h is independently hydrogen or (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.2)-alkoxy, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.2-C.sub.4)-alkenyl, (C.sub.1-C.sub.6)-alkoxycarbonyl-(C.sub.1-C.sub.6)-alkyl, or (C.sub.2-C.sub.4)-alkynyl, where each of the six last-mentioned radicals is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano, CO.sub.2R.sup.a, and (C.sub.1-C.sub.2)-alkoxy; each m is independently 0, 1, 2, 3, 4, or 5; each n is independently 0, 1, or 2; each p is independently 1, 2, or 3; r is 1, 2, 3, 4, 5, or 6; including agriculturally acceptable salts, stereoisomers, and tautomers.
2. The compound as claimed in claim 1, wherein one, two, three, or all four of the following conditions (a), (b), (c), and (d) apply: (a) R.sup.1 is hydrogen; and R.sup.9 is hydrogen; (b) R.sup.2 is hydrogen, halogen, or (C.sub.1-C.sub.3)-alkyl; and R.sup.6 is hydrogen, halogen, or (C.sub.1-C.sub.3)-alkyl; (c) R.sup.3 is hydrogen, halogen, (C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-haloalkyl, (C.sub.1-C.sub.3)-alkoxy, or (C.sub.1-C.sub.3)-haloalkoxy; and R.sup.5 is hydrogen, halogen, (C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-haloalkyl, (C.sub.1-C.sub.3)-alkoxy, or (C.sub.1-C.sub.3)-haloalkoxy; (d) R.sup.4 is hydrogen or halogen.
3. The compound as claimed in claim 1, wherein one, two, three, or all four of the following conditions (a), (b), (c), and (d) apply: (a) R.sup.1 is hydrogen; and R.sup.9 is hydrogen; (b) R.sup.2 is hydrogen; and R.sup.6 is hydrogen; (c) R.sup.3 is halogen, (C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-haloalkyl, (C.sub.1-C.sub.3)-alkoxy, or (C.sub.1-C.sub.3); and R.sup.5 is hydrogen or halogen; (d) R.sup.4 is hydrogen.
4. The compound as claimed in claim 1, wherein: R.sup.7 and R.sup.8, independently of each other, are (C.sub.1-C.sub.6)-alkyl or (C.sub.2-C.sub.6)-alkenyl.
5. The compound as claimed in claim 4, wherein: R.sup.7 and R.sup.8, independently of each other, are (C.sub.1-C.sub.4)-alkyl.
6. The compound as claimed in claim 5, wherein R.sup.7 and R.sup.8 are both methyl.
7. The compound as claimed in claim 1, wherein the substituents have the following meaning: X is a bond; and Y is Z; where Z is a three-, four-, five-, or six-membered saturated, partly unsaturated or fully unsaturated carbocyclic ring, except phenyl, which is substituted by p radicals selected from the group consisting of CO.sub.2R.sup.e, CONR.sup.bR.sup.h, S(O),R.sup.a, SO.sub.2NR.sup.bR.sup.a, SO.sub.2NR.sup.bCOR.sup.e, CORD, CONR.sup.eS(O)R.sup.a, CONR.sup.eSO.sub.2R.sup.a, CONR.sup.b1SO.sub.2NR.sup.b2R.sup.b3, NR.sup.bR.sup.e, NR.sup.bCOR.sup.e, NR.sup.bCONR.sup.eR.sup.e, NR.sup.bCO.sub.2R.sup.e, NR.sup.bSO.sub.2R.sup.e, NR.sup.b1SO.sub.2NR.sup.b2R.sup.e, OCONR.sup.bR.sup.e, OCSNR.sup.bR.sup.e, POR.sup.lR.sup.l, and C(R.sup.b)NOR.sup.e, and where the carbon ring atoms bear n oxo groups; or Z is a three-, four-, five-, or six-membered saturated, partly unsaturated or fully unsaturated heterocyclic ring containing one or two oxygen atoms as ring members, where the ring is substituted by p radicals selected from the group consisting of CO.sub.2R.sup.e, CONR.sup.bR.sup.h, S(O),R.sup.a, SO.sub.2NR.sup.bR.sup.a, SO.sub.2NR.sup.bCOR.sup.e, CORD, CONR.sup.eS(O)R.sup.a, CONR.sup.eSO.sub.2R.sup.a, CONR.sup.b1SO.sub.2NR.sup.b2R.sup.b3, NR.sup.bR.sup.e, NR.sup.bCOR.sup.e, NR.sup.bCONR.sup.eR.sup.e, NR.sup.bCO.sub.2R.sup.e, NR.sup.bSO.sub.2R.sup.e, NR.sup.b1SO.sub.2NR.sup.b2R.sup.e, OCONR.sup.bR.sup.e, OCSNR.sup.bR.sup.e, POR.sup.lR.sup.l, and C(R.sup.b)NOR.sup.e, and where the carbon ring atoms bear n oxo groups.
8. The compound as claimed in claim 7, where Z is a five- or six-membered saturated or partly unsaturated carbocyclic ring which is substituted by p radicals CO.sub.2R.sup.e, where R.sup.e is hydrogen or (C.sub.1-C.sub.6)-alkyl.
9. The compound as claimed in claim 1, wherein the substituents have the following meanings: X is a divalent unit (X.sup.1), where R.sup.10 and R.sup.11 are as defined in claim 1; Y is (C.sub.1-C.sub.8)-alkyl which is substituted by p radicals selected from the group consisting of CO.sub.2R.sup.e, CONR.sup.bR.sup.h, S(O),R.sup.a, SO.sub.2NR.sup.bR.sup.a, SO.sub.2NR.sup.bCOR.sup.e, CORD, CONR.sup.eS(O)R.sup.a, CONR.sup.eSO.sub.2R.sup.a, CONR.sup.b1SO.sub.2NR.sup.b2R.sup.b3, NR.sup.bR.sup.e, NR.sup.bCOR.sup.e, NR.sup.bCONR.sup.eR.sup.e, NR.sup.bCO.sub.2R.sup.e, NR.sup.bSO.sub.2R.sup.e, NR.sup.b1SO.sub.2NR.sup.b2R.sup.e, OCONR.sup.bR.sup.e, OCSNR.sup.bR.sup.e, POR.sup.lR.sup.l and C(R.sup.b)NOR.sup.e.
10. The compound as claimed in claim 9, wherein Y is (C.sub.1-C.sub.4)-alkyl which is substituted by p radicals CO.sub.2R.sup.e, where R.sup.e is hydrogen or (C.sub.1-C.sub.4)-alkyl.
11. The compound as claimed in claim 1, wherein p is 1 or 2.
12. The compound as claimed in claim 1, wherein the substituents have the following meaning: R.sup.1 hydrogen; R.sup.2 is hydrogen or halogen; R.sup.3 is hydrogen, halogen, (C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-haloalkyl, (C.sub.1-C.sub.3)-alkoxy, or (C.sub.1-C.sub.3)-haloalkoxy; R.sup.4 is hydrogen or halogen; R.sup.5 is hydrogen, halogen, (C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-haloalkyl, (C.sub.1-C.sub.3)-alkoxy, or (C.sub.1-C.sub.3)-haloalkoxy; R.sup.6 is hydrogen; R.sup.7 and R.sup.8, independently of each other, are (C.sub.1-C.sub.6)-alkyl; R.sup.9 hydrogen; and x is a bond; and Y is Z; where Z is a five- or six-membered saturated or partly unsaturated carbocyclic ring which is substituted by p radicals CO.sub.2R.sup.e, where R.sup.e is hydrogen or (C.sub.1-C.sub.6)-alkyl; or X is a divalent unit (X.sup.1), where R.sup.10 and R.sup.11 are independently of each other hydrogen or (C.sub.1-C.sub.6)-alkyl; and Y is (C.sub.1-C.sub.4)-alkyl which is substituted by p radicals selected from the group consisting of CO.sub.2R.sup.e, CONR.sup.bR.sup.h, CONR.sup.eS(O)R.sup.a, CONR.sup.eSO.sub.2R.sup.a, and CONR.sup.b1SO.sub.2NR.sup.b2R.sup.b3, where R.sup.e in CO.sub.2R.sup.e is hydrogen, (C.sub.1-C.sub.6)-alkyl which optionally has a cyano substituent; (C.sub.2-C.sub.4)-alkynyl or phenyl-(C.sub.1-C.sub.3)-alkyl; R.sup.b in CONR.sup.bR.sup.h is hydrogen or (C.sub.1-C.sub.3)-alkyl; R.sup.h in CONR.sup.bR.sup.h is (C.sub.1-C.sub.3)-alkoxy; R.sup.e in CONR.sup.eS(O)R.sup.a is hydrogen or (C.sub.1-C.sub.3)-alkyl; R.sup.a in CONR.sup.eS(O)R.sup.a is (C.sub.1-C.sub.6)-alkyl or (C.sub.1-C.sub.3)-haloalkyl; R.sup.e in CONR.sup.eSO.sub.2R.sup.a is hydrogen or (C.sub.1-C.sub.3)-alkyl; R.sup.a in CONR.sup.eSO.sub.2R.sup.a is (C.sub.1-C.sub.6)-alkyl or (C.sub.1-C.sub.3)-haloalkyl; in CONR.sup.b1SO.sub.2NR.sup.b2R.sup.b3 is hydrogen or (C.sub.1-C.sub.3)-alkyl; R.sup.b2 in CONR.sup.b1SO.sub.2NR.sup.b2R.sup.b3 is hydrogen or (C.sub.1-C.sub.3)-alkyl; R.sup.b3 in CONR.sup.b1SO.sub.2NR.sup.b2R.sup.b3 is (CC.sub.6)-alkyl; or R.sup.b2 and R.sup.b3, together with the nitrogen atom they are bound to, form a saturated 5- or 6-membered N-bound heterocyclic ring; and p is 1 or 2.
13. The compound as claimed in claim 12, where the substituents have the following meaning: R hydrogen; R.sup.2 is hydrogen; R.sup.3 is hydrogen, halogen, (C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-haloalkyl, (C.sub.1-C.sub.3)-alkoxy, or (C.sub.1-C.sub.3)-haloalkoxy; R.sup.4 is hydrogen; R.sup.5 is hydrogen or halogen; R.sup.6 is hydrogen; R.sup.7 and R.sup.8, independently of each other, are (C.sub.1-C.sub.4)-alkyl; R.sup.9 hydrogen; and X is a bond; and Y is Z; where Z is a five-membered partly unsaturated carbocyclic ring which is substituted by p radicals CO.sub.2R.sup.e, where R.sup.e is hydrogen or (C.sub.1-C.sub.6)-alkyl; or X is a divalent unit (X.sup.1), where R.sup.10 and R.sup.11 are independently of each other hydrogen or methyl; and Y is (C.sub.1-C.sub.4)-alkyl which is substituted by p radicals CO.sub.2R.sup.e, where R.sup.e is hydrogen or (C.sub.1-C.sub.6)-alkyl; and p is 1.
14. The compound as claimed in claim 13, where the substituents have the following meaning: R hydrogen; R.sup.2 is hydrogen; R.sup.3 is halogen, (C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-haloalkyl, (C.sub.1-C.sub.3)-alkoxy or (C.sub.1-C.sub.3)-haloalkoxy; R.sup.4 is hydrogen; R.sup.5 is hydrogen or halogen; R.sup.6 is hydrogen; R.sup.7 and R.sup.8 are methyl; R.sup.9 hydrogen; and X is a bond; and Y is Z; where Z is a five-membered partly unsaturated carbocyclic ring which is substituted by p radicals CO.sub.2R.sup.e, where R.sup.e is hydrogen or (C.sub.1-C.sub.4)-alkyl; or X is a divalent unit (X.sup.1), where one of R.sup.10 and R.sup.11 is hydrogen and the other is methyl; and Y is (C.sub.1-C.sub.4)-alkyl which is substituted by p radicals CO.sub.2R.sup.e, where R.sup.e is (C.sub.1-C.sub.4)-alkyl; and p is 1.
15. The compound as claimed in claim 1, wherein-X-Y form together a group of the formula (XY1) or (XY2) ##STR00115## where # designates the attachment point to NR.sup.9; R.sup.A, R.sup.B, R.sup.C, R.sup.D, R.sup.E, and R.sup.F, independently of each other, have one of the meanings given for R.sup.10 and R.sup.11; or R.sup.A and R.sup.C, together with the carbon atoms they are bound to, form a 3-, 4-, 5-, or 6-membered saturated or partially unsaturated carbocyclic ring; or R.sup.C and R.sup.E, together with the carbon atoms they are bound to, form a 3-, 4-, 5-, or 6-membered saturated or partially unsaturated carbocyclic ring; or R.sup.A and R.sup.E, together with the carbon atoms they are bound to, form a 3-, 4-, 5-, or 6-membered saturated or partially unsaturated carbocyclic ring; or R.sup.A and R.sup.C, together with the carbon atoms they are bound to, form a 3-, 4-, 5-, or 6-membered saturated or partially unsaturated heterocyclic ring containing 1 or 2 oxygen atoms as ring members; or R.sup.C and R.sup.E, together with the carbon atoms they are bound to, form a 3-, 4-, 5-, or 6-membered saturated or partially unsaturated heterocyclic ring containing 1 or 2 oxygen atoms as ring members; or R.sup.A and R.sup.E, together with the carbon atoms they are bound to, form a 3-, 4-, 5-, or 6-membered saturated or partially unsaturated heterocyclic ring containing 1 or 2 oxygen atoms as ring members.
16. The compound as claimed in claim 15, where R.sup.A is hydrogen or methyl; and R.sup.B, R.sup.C, R.sup.D, R.sup.E, and R.sup.F are hydrogen; or R.sup.A and R.sup.E, together with the carbon atoms they are bound to, form a 5- or 6-membered saturated or partly unsaturated carbocyclic ring; and R.sup.B, R.sup.C, R.sup.D_and R.sup.F are hydrogen; or R.sup.A and R.sup.E, together with the carbon atoms they are bound to, form a 5- or 6-membered saturated or partly unsaturated heterocyclic ring containing one oxygen atom as ring member; and R.sup.B, R.sup.C, R.sup.D and R.sup.F are hydrogen; and R.sup.e is hydrogen or (C.sub.1-C.sub.4)-alkyl.
17. A composition comprising at least one compound as claimed in claim 1, and at least one auxiliary, which is customary for formulating crop protection compounds.
18. The composition as claimed in claim 17 comprising a further herbicide.
19. (canceled)
20. A method for controlling unwanted vegetation which comprises contacting an herbicidally effective amount of at least one compound as claimed in claim 1, with a plant, its seed and/or its habitat.
Description
DETAILED DESCRIPTION OF THE INVENTION
Definitions:
[0046] Depending on the kind of substituents, the compounds of formula (I) may have one or more centers of chirality, in which case they may be present as mixtures of enantiomers or diastereomers but also in the form of the pure enantiomers or pure diastereomers. The invention provides both the pure enantiomers or pure diastereomers of the compounds of formula I, and their mixtures and the use according to the invention of the pure enantiomers or pure diastereomers of the compound of formula I or its mixtures. Suitable compounds of formula I also include all possible geometrical stereoisomers (cis/trans isomers) as a specific form of diastereomers and mixtures thereof. Cis/trans isomers may be present with respect to an alkene, carbon-nitrogen doublebond, nitrogen-sulfur double bond, amide group or a cyclic, non-aromatic moiety. The term stereoisomer(s) encompasses both optical isomers, such as enantiomers or diastereomers existing due to more than one stereogenic center in the molecule, as well as geometrical isomers (cis/trans isomers). Just by way of example, a stereogenic center is the C atom carrying R.sup.10 and R.sup.11 in X.sup.1 to X.sup.6, provided of course that R.sup.10 and R.sup.11 are different. Another example for a stereogenic center is the C atom carrying R.sup.7 and R.sup.8, provided, of course, that R.sup.7 and R.sup.8 are different from each other.
[0047] If the above-mentioned herbicidal compounds B and/or the safeners C have one or more centres of chirality they may also be present as enantiomers or diastereomers, and it is possible to use both the pure enantiomers and diastereomers or their mixtures.
[0048] If the compounds of formula (I), the herbicidal compounds B and/or the safeners C as described herein have ionizable functional groups, they can also be employed in the form of their agriculturally acceptable salts. Suitable are, in general, the salts of those cations and the acid addition salts of those acids whose cations and anions, respectively, have no adverse effect on the activity of the active compounds.
[0049] Preferred cations are the ions of the alkali metals, preferably of lithium, sodium and potassium, of the alkaline earth metals, preferably of calcium and magnesium, and of the transition metals, preferably of manganese, copper, zinc and iron, further ammonium and substituted ammonium in which one to four hydrogen atoms are replaced by C.sub.1-C.sub.4-alkyl, hydroxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl, hydroxy-C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl, phenyl or benzyl, preferably ammonium, methylammonium, isopropylammonium, dimethylammonium, diethylammonium, diisopropylammonium, trimethylammonium, triethylammonium, tris(isopropyl) ammonium, heptylammonium, dodecylammonium, tetradecylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium (olamine salt), 2-(2-hydroxyeth-1-oxy) eth-1-ylammonium (diglycolamine salt), di(2-hydroxyeth-1-yl) ammonium (diolamine salt), tris(2-hydroxyethyl) ammonium (trolamine salt), tris(2-hydroxypropyl) ammonium, benzyltrimethylammonium, benzyltriethylammonium, N,N, N-trimethylethanolammonium (choline salt), furthermore phosphonium ions, sulfonium ions, preferably tri (C.sub.1-C.sub.4-alkyl) sulfonium, such as trimethylsulfonium, and sulfoxonium ions, preferably tri (C.sub.1-C.sub.4-alkyl) sulfoxonium, and finally the salts of polybasic amines such as N, N-bis-(3-aminopropyl)methylamine and diethylenetriamine.
[0050] Anions of useful acid addition salts are primarily chloride, bromide, fluoride, iodide, hydrogensulfate, methylsulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and also the anions of C.sub.1-C.sub.4-alkanoic acids, preferably formate, acetate, propionate and butyrate.
[0051] The compounds (I) may be present in form of different tautomers. For instance, if ring Z is a lactam, i.e. contains an amide group as ring member (=unsubstituted, secondary nitrogen ring atom neighboured to a carbon ring atom carrying an oxo group), this ring moiety N(H)C(O) can be in equilibrium with its tautomeric form NC(OH). The same applies to the two mandatorily present amide groups of the malonamide moiety N(R.sup.1)C(O)C(R.sup.7) (R.sup.8)C(O)N(R.sup.9) if one or both of R.sup.1 and R.sup.9 are hydrogen: [0052] If only R.sup.1 is hydrogen, the malonamide moiety can be present as N(H)C(O)C(R.sup.7) (R.sup.8)C(O)N(R.sup.9) or as NC(OH)C(R.sup.7) (R.sup.8)C(O)N(R.sup.9) or as a mixture of the two forms; [0053] If only R.sup.9 is hydrogen, the malonamide moiety can be present as N(R.sup.1)C(O)C(R.sup.7) (R.sup.8)C(O)N(H) or as N(R.sup.1)C(O)C(R.sup.7) (R.sup.8)C(OH)N or as a mixture of the two forms; [0054] If both of R.sup.1 and R.sup.9 are hydrogen, the malonamide moiety can be present as N(H)C(O)C(R.sup.7) (R.sup.8)C(O)N(H) or as NC(OH)C(R.sup.7) (R.sup.8)C(O)N(H) or as N(H)C(O)C(R.sup.7) (R.sup.8)C(OH)N or as NC(OH)C(R.sup.7) (R.sup.8)C(OH)N or as mixture of two, three all four of the above forms.
[0055] The amount in which the one or other tautomeric form is present depends on the complete molecular structure and even stronger on the surrounding conditions (presence or absence of solvent, type of solvent, pH, temperature etc.).
[0056] The term undesired vegetation (weeds) is understood to include any vegetation growing in non-crop-areas or at a crop plant site or locus of seeded and otherwise desired crop, where the vegetation is any plant species, including their germinant seeds, emerging seedlings and established vegetation, other than the seeded or desired crop (if any). Weeds, in the broadest sense, are plants considered undesirable in a particular location.
[0057] The organic moieties mentioned in the above definitions of the variables arelike the term halogen-collective terms for individual listings of the individual group members. The prefix C.sub.n-C.sub.m indicates in each case the possible number of carbon atoms in the group.
[0058] The term halogen denotes in each case fluorine, bromine, chlorine or iodine, in particular fluorine, chlorine or bromine.
[0059] The term partially or completely halogenated will be taken to mean that 1 or more, e.g. 1, 2, 3, 4 or 5 or all of the hydrogen atoms of a given radical have been replaced by a halogen atom, in particular by fluorine or chlorine. A partially or completely halogenated radical is termed below also halo-radical. For example, partially or completely halogenated alkyl is also termed haloalkyl.
[0060] The term alkyl as used herein (and in the alkyl moieties of other groups comprising an alkyl group, e.g. alkoxy, alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylthio, alkylsulfonyl and alkoxyalkyl) denotes in each case a straight-chain or branched alkyl group having usually from 1 to 12 carbon atoms (C.sub.1-C.sub.12-alkyl), frequently from 1 to 6 carbon atoms (C.sub.1-C.sub.6-alkyl), in particular 1 to 4 carbon atoms (C.sub.1-C.sub.4-alkyl) and especially from 1 to 3 carbon atoms (C.sub.1-C.sub.3-alkyl) or 1 or 2 carbon atoms (C.sub.1-C.sub.2-alkyl). C.sub.1-C.sub.2-Alkyl is methyl or ethyl. C.sub.1-C.sub.3-Alkyl is methyl, ethyl, npropyl or iso-propyl. Examples of C.sub.1-C.sub.4-alkyl are methyl, ethyl, n-propyl, iso-propyl, nbutyl, 2-butyl(=sec-butyl), isobutyl and tert-butyl. Examples for C.sub.1-C.sub.6-alkyl are, in addition to those mentioned for C.sub.1-C.sub.4-alkyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl. Examples for C.sub.1-C.sub.8-alkyl are, in addition to those mentioned for C.sub.1-C.sub.6-alkyl, n-heptyl, 1-methylhexyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5-methylhexyl, 1-ethylpentyl, 2-ethylpentyl, 3-ethylpentyl, n-octyl, 1-methylheptyl, 2-methylheptyl, 1-ethylhexyl, 2-ethylhexyl, 1,2-dimethylhexyl, 1-propylpentyl and 2-propylpentyl. Examples for C.sub.1-C.sub.12-alkyl are, apart those mentioned for C.sub.1-C.sub.6-alkyl, nonyl, decyl, 2-propylheptyl, 3-propylheptyl, undecyl, dodecyl and positional isomers thereof.
[0061] The term haloalkyl as used herein (and in the haloalkyl moieties of other groups comprising a haloalkyl group, e.g. haloalkoxy, haloalkylthio, haloalkylcarbonyl, haloalkylsulfonyl and haloalkylsulfinyl), which is also expressed as alkyl which is partially or fully halogenated, denotes in each case a straight-chain or branched alkyl group having usually from 1 to 6 carbon atoms (C.sub.1-C.sub.6-haloalkyl), more frequently 1 to 3 carbon atoms (C.sub.1-C.sub.3-haloalkyl), as defined above, wherein the hydrogen atoms of this group are partially or totally replaced with halogen atoms. Preferred haloalkyl moieties are selected from C.sub.1-C.sub.3-haloalkyl, specifically from C.sub.1-C.sub.2-haloalkyl, in particular from fluorinated C.sub.1-C.sub.2-alkyl. Examples for C.sub.1-C.sub.2-haloalkyl are fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, bromomethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, pentafluoroethyl, 1-chloroethyl, 2-chloroethyl, 2,2, dichloroethyl, 2,2,2-trichloroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 1-bromoethyl, and the like. Examples for C.sub.1-C.sub.3-haloalkyl are, in addition to those mentioned for C.sub.1-C.sub.2-haloalkyl, 1-fluoropropyl, 2-fluoropropyl, 3 -fluoropropyl, 3,3-difluoropropyl, 3,3,3-trifluoropropyl, heptafluoropropyl, 1,1,1-trifluoroprop-2-yl, 3-chloropropyl, and the like.
[0062] The term hydroxyalkyl denotes in each case a straight-chain or branched alkyl group having usually from 1 to 6 carbon atoms (C.sub.1-C.sub.6-hydroxyalkyl), more frequently 1 to 3 carbon atoms (C.sub.1-C.sub.3-hydroxyalkyl), as defined above, wherein one hydrogen atom of this group is replaced with a hydroxyl group. Examples are hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 1-hydroxypropyl, 2-hydroxypropyl, 3-hydroxypropyl, 1-hydroxy-2-propyl and the like.
[0063] The term alkenyl as used herein denotes in each case a monounsaturated straight-chain or branched hydrocarbon radical having usually 2 to 12 (C.sub.2-C.sub.12-alkenyl), preferably 2 to 6 carbon atoms (C.sub.2-C.sub.6-alkenyl), e.g. 3 to 6 carbon atoms (C.sub.3-C.sub.6-alkenyl), in particular 2 or 3 carbon atoms (C.sub.2-C.sub.3-alkenyl), and a double bond in any position, for example C.sub.2-C.sub.3-alkenyl, such as ethenyl, 1-propenyl, 2-propenyl or 1-methylethenyl; C.sub.2-C.sub.6-alkenyl, such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl, 1-ethyl-2-methyl-2-propenyl and the like, or C.sub.2-C.sub.12-alkenyl, such as the radicals mentioned for C.sub.2-C.sub.6-alkenyl and additionally 1-heptenyl, 2-heptenyl, 3-heptenyl, 1-octenyl, 2-octenyl, 3-octenyl, 4-octenyl, the nonenyls, decenyls, undecenyls, dodecenyls and the positional isomers thereof.
[0064] Examples for C.sub.3-C.sub.6-alkenyl are those mentioned above for C.sub.2-C.sub.6-alkenyl, except for ethenyl.
[0065] The term haloalkenyl as used herein, which may also be expressed as alkenyl which is substituted by halogen, and the haloalkenyl moieties in haloalkenyloxy and the like refers to unsaturated straight-chain or branched hydrocarbon radicals having 2 to 6 (C.sub.2-C.sub.6-haloalkenyl) or 2 to 3 (C.sub.2-C.sub.3-haloalkenyl) carbon atoms and a double bond in any position, where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine, for example chlorovinyl, chloroallyl and the like.
[0066] The term alkynyl as used herein denotes unsaturated straight-chain or branched hydrocarbon radicals having usually 2 to 12 (C.sub.2-C.sub.12-alkynyl), frequently 2 to 6 (C.sub.2-C.sub.6-alkynyl), preferably 2 to 4 carbon atoms (C.sub.2-C.sub.4-alkynyl) or 2 to 3 carbon atoms (C.sub.2-C.sub.3-alkynyl) and a triple bond in any position, for example C.sub.2-C.sub.3-alkynyl, such as ethynyl, 1-propynyl or 2-propynyl; C.sub.2-C.sub.4-alkynyl, such as ethynyl, 1-propynyl or 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl and the like; C.sub.2-C.sub.6-alkynyl, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl, 1-ethyl-1-methyl-2-propynyl and the like.
[0067] The term haloalkynyl as used herein, which is also expressed as alkynyl which is substituted by halogen, refers to unsaturated straight-chain or branched hydrocarbon radicals having usually 2 to 6 carbon atoms (C.sub.2-C.sub.6-haloalkynyl), preferabyl 2 or 3 carbon atoms (C.sub.2-C.sub.3-haloalkynyl), and a triple bond in any position (as mentioned above), where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine.
[0068] The term cycloalkyl as used herein (and in the cycloalkyl moieties of other groups comprising a cycloalkyl group, e.g. cycloalkoxy and cycloalkylalkyl) denotes in each case a mono- or bicyclic, saturated cycloaliphatic radical having usually from 3 to 8 carbon atoms (C.sub.3-C.sub.8-cycloalkyl), preferably 3 to 6 carbon atoms (C.sub.3-C.sub.6-cycloalkyl), 3 to 5 carbon atoms (C.sub.3-C.sub.5-cycloalkyl) or 3 to 4 carbon atoms (C.sub.3-C.sub.4-cycloalkyl) as (only) ring members. Examples of monocyclic saturated cycloaliphatic radicals having 3 or 4 carbon atoms comprise cyclopropyl and cyclobutyl. Examples of monocyclic saturated cycloaliphatic radicals having 3 to 5 carbon atoms comprise cyclopropyl, cyclobutyl and cyclopentyl. Examples of monocyclic saturated cycloaliphatic radicals having 3 to 6 carbon atoms comprise cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. Examples of monocyclic saturated cycloaliphatic radicals having 3 to 8 carbon atoms comprise cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl. C.sub.5-C.sub.6-Cycloalkyl is cyclopentyl or cyclohexyl. Examples of bicyclic radicals having 6 to 8 carbon atoms comprise bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl, bicyclo [3.1.1]heptyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl and bicyclo[3.2.1]octyl.
[0069] The term halocycloalkyl as used herein (and in the halocycloalkyl moieties of other groups comprising an halocycloalkyl group) denotes in each case a mono- or bicyclic cycloaliphatic radical having usually from 3 to 8 carbon atoms (C.sub.3-C.sub.8-halocycloalkyl), preferably 3 to 5 carbon atoms (C.sub.3-C.sub.5-halocycloalkyl), wherein at least one, e.g. 1, 2, 3, 4 or 5 of the hydrogen atoms are replaced by halogen, in particular by fluorine or chlorine. Examples are 1- and 2-fluorocyclopropyl, 1,2-, 2,2- and 2,3-difluorocyclopropyl, 1,2,2-trifluorocyclopropyl, 2,2,3,3-tetrafluorocyclpropyl, 1- and 2-chlorocyclopropyl, 1,2-, 2,2- and 2,3-dichlorocyclopropyl, 1,2,2-trichlorocyclopropyl, 2,2,3,3-tetrachlorocyclpropyl, 1-, 2- and 3-fluorocyclopentyl, 1,2-, 2,2-, 2,3-, 3,3-, 3,4-, 2,5-difluorocyclopentyl, 1-, 2- and 3-chlorocyclopentyl, 1,2-, 2,2-, 2,3-, 3,3-, 3,4-, 2,5-dichlorocyclopentyl and the like.
[0070] The term hydroxycycloalkyl denotes in each case a mono- or bicyclic cycloaliphatic radical having usually from 3 to 6 carbon atoms (hydroxy-(C.sub.3-C.sub.6)-cycloalkyl), preferably 3 to 5 carbon atoms (hydroxy-(C.sub.3-C.sub.5)-cycloalkyl), wherein at least one, e.g. 1, 2, 3, 4 or 5 of the hydrogen atoms are replaced by a hydroxyl group. Examples are 1-hydroxycyclopropyl, 2-hydroxycyclopropyl, 1,2-dihydroxycyclopropyl, 2,3-dihydroxycyclopropyl, 1-hydroxycyclobutyl, 2-hydroxycyclobutyl, 3-hydroxycyclobutyl, 1,2-dihydroxycyclobutyl, 1,3-dihydroxycyclobutyl, 2,3-dihydroxycyclobutyl, 1-hydroxycyclopentyl, 2-hydroxycyclopentyl, 3-hydroxycyclopentyl, 1,2-dihydroxycyclopentyl, 1,3-dihydroxycyclopentyl, 2,3-dihydroxycyclopentyl and the like.
[0071] The term alkoxy as used herein denotes in each case a straight-chain or branched alkyl group usually having from 1 to 6 carbon atoms (C.sub.1-C.sub.6-alkoxy), preferably 1 to 3 carbon atoms (C.sub.1-C.sub.3-alkoxy), in particular 1 or 2 carbon atoms (C.sub.1-C.sub.2-alkoxy), which is bound to the remainder of the molecule via an oxygen atom. C.sub.1-C.sub.2-Alkoxy is methoxy or ethoxy. C.sub.1-C.sub.3-Alkoxy is additionally, for example, n-propoxy or 1-methylethoxy (isopropoxy). C.sub.1-C.sub.6-Alkoxy is additionally, for example, butoxy, 1-methylpropoxy (sec-butoxy), 2-methylpropoxy (isobutoxy) or 1,1-dimethylethoxy (tertbutoxy), pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy or 1-ethyl-2-methylpropoxy.
[0072] The term haloalkoxy as used herein denotes in each case a straight-chain or branched alkoxy group, as defined above, having from 1 to 6 carbon atoms (C.sub.1-C.sub.6-haloalkoxy), preferably 1 to 3 carbon atoms (C.sub.1-C.sub.3-haloalkoxy), in particular 1 or 2 carbon atoms (C.sub.1-C.sub.2-haloalkoxy), wherein the hydrogen atoms of this group are partially or totally replaced with halogen atoms, in particular fluorine atoms (in this case, the radical is also termed fluorinated alkoxy). C.sub.1-C.sub.2-Haloalkoxy is, for example, OCH.sub.2F, OCHF.sub.2, OCF.sub.3, OCH.sub.2Cl, OCHCl.sub.2, OCCl.sub.3, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy or OC.sub.2F.sub.5. C.sub.1-C.sub.3-Haloalkoxy is additionally, for example, 2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, OCH.sub.2-C.sub.2F.sub.5, OCF.sub.2-C.sub.2F.sub.5, 1-(CH.sub.2F)-2-fluoroethoxy, 1-(CH.sub.2Cl)-2-chloroethoxy or 1-(CH.sub.2Br)-2-bromoethoxy. C.sub.1-C.sub.6-Haloalkoxy is additionally, for example, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy, 5-fluoropentoxy, 5-chloropentoxy, 5-brompentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or dodecafluorohexoxy.
[0073] The term alkenyloxy denotes an alkenyl group, as defined above, attached via an oxygen atom to the remainder of the molecule. C.sub.2-C.sub.6-Alkenyloxy is a C.sub.2-C.sub.6-alkenyl group, as defined above, attached via an oxygen atom to the remainder of the molecule. C.sub.3-C.sub.6-Alkenyloxy is a C.sub.3-C.sub.6-alkenyl group, as defined above, attached via an oxygen atom to the remainder of the molecule.
[0074] The term haloalkenyloxy denotes a haloalkenyl group, as defined above, attached via an oxygen atom to the remainder of the molecule. C.sub.2-C.sub.6-Haloalkenyloxy is a C.sub.2-C.sub.6-haloalkenyl group, as defined above, attached via an oxygen atom to the remainder of the molecule. C.sub.3-C.sub.6-Haloalkenyloxy is a C.sub.3-C.sub.6-haloalkenyl group, as defined above, attached via an oxygen atom to the remainder of the molecule.
[0075] The term alkynyloxy denotes an alkynyl group, as defined above, attached via an oxygen atom to the remainder of the molecule. C.sub.2-C.sub.6-Alkynyloxy is a C.sub.2-C.sub.6-alkynyl group, as defined above, attached via an oxygen atom to the remainder of the molecule. C.sub.3-C.sub.6-Alkynyloxy is a C.sub.3-C.sub.6-alkynyl group, as defined above, attached via an oxygen atom to the remainder of the molecule.
[0076] The term haloalkynyloxy denotes a haloalkynyl group, as defined above, attached via an oxygen atom to the remainder of the molecule. C.sub.2-C.sub.6-Haloalkynyloxy is a C.sub.2-C.sub.6-haloalkynyl group, as defined above, attached via an oxygen atom to the remainder of the molecule. C.sub.3-C.sub.6-Haloalkynyloxy is a C.sub.3-C.sub.6-haloalkynyl group, as defined above, attached via an oxygen atom to the remainder of the molecule.
[0077] The term cycloalkoxy denotes a cycloalkyl group, as defined above, attached via an oxygen atom to the remainder of the molecule. C.sub.3-C.sub.6-Cycloalkoxy is a C.sub.3-C.sub.6-cycloalkyl group, as defined above, attached via an oxygen atom to the remainder of the molecule. Examples of C.sub.3-C.sub.6-cycloalkoxy comprise cyclopropoxy, cyclobutoxy, cyclopentoxy and cyclohexoxy.
[0078] The term alkoxy-alkoxy as used herein, refers to an alkoxy group, as defined above, where one hydrogen atom is replaced by another alkoxy group, as defined above. The term C.sub.1-C.sub.3-alkoxy-C.sub.1-C.sub.3-alkoxy as used herein, refers to an alkoxy group having 1 to 3 carbon atoms, as defined above, where one hydrogen atom is replaced by a C.sub.1-C.sub.3-alkoxy group, as defined above. Examples are methoxymethoxy, ethoxymethoxy, propoxymethoxy, isopropoxymethoxy, 1-methoxyethoxy, 1-ethoxyethoxy, 1-propoxyethoxy, 1-isopropoxyethoxy, 2-methoxyethoxy, 2-ethoxyethoxy, 2-propoxyethoxy, 2-isopropoxyethoxy, 1-methoxypropoxy, 1-ethoxypropoxy, 1-propoxypropoxy, 1-isopropoxypropoxy, 2-methoxypropoxy, 2-ethoxypropoxy, 2-propoxypropoxy, 2-isopropoxypropoxy, 3-methoxypropoxy, 3-ethoxypropoxy, 3-propoxypropoxy, 3-isopropoxypropoxy, and the like.
[0079] The term alkylthio (also alkylsulfanyl or alkyl-S) as used herein denotes in each case a straight-chain or branched saturated alkyl group as defined above, usually comprising 1 to 6 carbon atoms (C.sub.1-C.sub.6-alkylthio), preferably 1 to 3 carbon atoms (C.sub.1-C.sub.3-alkylthio), which is attached via a sulfur atom at any position in the alkyl group. C.sub.1-C.sub.2-Alkylthio is methylthio or ethylthio. C.sub.1-C.sub.3-Alkylthio is additionally, for example, npropylthio or 1-methylethylthio(isopropylthio). C.sub.1-C.sub.6-Alkylthio is additionally, for example, butylthio, 1-methylpropylthio(sec-butylthio), 2-methylpropylthio(isobutylthio), 1,1-dimethylethylthio(tert-butylthio), pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio or 1-ethyl-2-methylpropylthio.
[0080] The term haloalkylthio as used herein refers to an alkylthio group as defined above wherein the hydrogen atoms are partially or completely substituted by fluorine, chlorine, bromine and/or iodine. C.sub.1-C.sub.2-Haloalkylthio is, for example, SCH.sub.2F, SCHF.sub.2, SCF.sub.3, SCH.sub.2Cl, SCHCl.sub.2, SCCl.sub.3, chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 2-fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, 2,2,2-trichloroethylthio or SC.sub.2F.sub.5. C.sub.1-C.sub.4-Haloalkylthio is additionally, for example, 2-fluoropropylthio, 3-fluoropropylthio, 2,2-difluoropropylthio, 2,3-difluoropropylthio, 2-chloropropylthio, 3-chloropropylthio, 2,3-dichloropropylthio, 2-bromopropylthio, 3-bromopropylthio, 3,3,3-trifluoropropylthio, 3,3,3-trichloropropylthio, SCH.sub.2-C.sub.2F.sub.5, SCF.sub.2-C.sub.2F.sub.5, 1-(CH.sub.2F)-2-fluoroethylthio, 1-(CH.sub.2Cl)-2-chloroethylthio, 1-(CH.sub.2Br)-2-bromoethylthio, 4-fluorobutylthio, 4-chlorobutylthio, 4-bromobutylthio or nonafluorobutylthio. C.sub.1-C.sub.6-Haloalkylthio is additionally, for example, 5-fluoropentylthio, 5-chloropentylthio, 5-brompentylthio, 5-iodopentylthio, undecafluoropentylthio, 6-fluorohexylthio, 6-chlorohexylthio, 6-bromohexylthio, 6-iodohexylthio or dodecafluorohexylthio.
[0081] The term alkylsulfinyl denotes an alkyl group, as defined above, attached via a sulfinyl [S(O)] group. For example, the term C.sub.1-C.sub.2-alkylsulfinyl refers to a C.sub.1-C.sub.2-alkyl group, as defined above, attached via a sulfinyl [S(O)] group. The term C.sub.1-C.sub.3-alkylsulfinyl refers to a C.sub.1-C.sub.3-alkyl group, as defined above, attached via a sulfinyl [S(O)] group. The term C.sub.1-C.sub.6-alkylsulfinyl refers to a C.sub.1-C.sub.6-alkyl group, as defined above, attached via a sulfinyl [S(O)] group. C.sub.1-C.sub.2-alkylsulfinyl is methylsulfinyl or ethylsulfinyl. C.sub.1-C.sub.3-alkylsulfinyl is additionally, for example, n-propylsulfinyl or 1-methylethylsulfinyl(isopropylsulfinyl). C.sub.1-C.sub.6-alkylsulfinyl is additionally, for example, butylsulfinyl, 1-methylpropylsulfinyl(sec-butylsulfinyl), 2-methylpropylsulfinyl(isobutylsulfinyl), 1,1-dimethylethylsulfinyl(tert-butylsulfinyl), pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, 1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, 2,2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, hexylsulfinyl, 1-methylpentylsulfinyl, 2-methylpentylsulfinyl, 3-methylpentylsulfinyl, 4-methylpentylsulfinyl, 1,1-dimethylbutylsulfinyl, 1,2-dimethylbutylsulfinyl, 1,3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl, 3,3-dimethylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl, 1,1,2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl, 1-ethyl-1-methylpropylsulfinyl or 1-ethyl-2-methylpropylsulfinyl.
[0082] The term haloalkylsulfinyl denotes a haloalkyl group, as defined above, attached via a sulfinyl [S(O)] group to the remainder of the molecule. C.sub.1-C.sub.2-Haloalkylsulfinyl is, for example, S(O)CH.sub.2F, S(O)CHF.sub.2, S(O)CF.sub.3, S(O)CH.sub.2Cl, S(O)CHCl.sub.2, S(O)CCl.sub.3, chlorofluoromethylsulfinyl, dichlorofluoromethylsulfinyl, chlorodifluoromethylsulfinyl, 2-fluoroethylsulfinyl, 2-chloroethylsulfinyl, 2-bromoethylsulfinyl, 2-iodoethylsulfinyl, 2,2-difluoroethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, 2-chloro-2-fluoroethylsulfinyl, 2-chloro-2,2-difluoroethylsulfinyl, 2,2-dichloro-2-fluoroethylsulfinyl, 2,2,2-trichloroethylsulfinyl or S(O) C.sub.2F.sub.5. C.sub.1-C.sub.3-Haloalkylsulfinyl is additionally, for example, 2-fluoropropylsulfinyl, 3-fluoropropylsulfinyl, 2,2-difluoropropylsulfinyl, 2,3-difluoropropylsulfinyl, 2-chloropropylsulfinyl, 3-chloropropylsulfinyl, 2,3-dichloropropylsulfinyl, 2-bromopropylsulfinyl, 3-bromopropylsulfinyl, 3,3,3-trifluoropropylsulfinyl, 3,3,3-trichloropropylsulfinyl, S(O)CH.sub.2-C.sub.2F.sub.5, S(O)CF.sub.2-C.sub.2F.sub.5, 1-(CH.sub.2F)-2-fluoroethylsulfinyl, 1-(CH.sub.2Cl)-2-chloroethylsulfinylor 1-(CH.sub.2Br)-2-bromoethylsulfinyl. C.sub.1-C.sub.4-Haloalkylsulfinyl is additionally, for example, 4-fluorobutylsulfinyl, 4-chlorobutylsulfinyl, 4-bromobutylsulfinyl or nonafluorobutylsulfinyl. C.sub.1-C.sub.6-Haloalkylsulfinyl is additionally, for example, 5-fluoropentylsulfinyl, 5-chloropentylsulfinyl, 5-brompentylsulfinyl, 5-iodopentylsulfinyl, undecafluoropentylsulfinyl, 6-fluorohexylsulfinyl, 6-chlorohexylsulfinyl, 6-bromohexylsulfinyl, 6-iodohexylsulfinyl or dodecafluorohexylsulfinyl.
[0083] The term alkylsulfonyl denotes an alkyl group, as defined above, attached via a sulfonyl [S(O).sub.2] group. The term C.sub.1-C.sub.2-alkylsulfonyl refers to a C.sub.1-C.sub.2-alkyl group, as defined above, attached via a sulfonyl [S(O).sub.2] group. The term C.sub.1-C.sub.3-alkylsulfonyl refers to a C.sub.1-C.sub.3-alkyl group, as defined above, attached via a sulfonyl [S(O).sub.2] group. The term C.sub.1-C.sub.6-alkylsulfonyl refers to a C.sub.1-C.sub.6-alkyl group, as defined above, attached via a sulfonyl [S(O).sub.2] group. C.sub.1-C.sub.2-alkylsulfonyl is methylsulfonyl or ethylsulfonyl. C.sub.1-C.sub.3-alkylsulfonyl is additionally, for example, n-propylsulfonyl or 1-methylethylsulfonyl(isopropylsulfonyl). C.sub.1-C.sub.6-alkylsulfonyl is additionally, for example, butylsulfonyl, 1-methylpropylsulfonyl(sec-butylsulfonyl), 2-methylpropylsulfonyl(isobutylsulfonyl), 1,1-dimethylethylsulfonyl (tert-butylsulfonyl), pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl, 1-ethyl-1-methylpropylsulfonyl or 1-ethyl-2-methylpropylsulfonyl.
[0084] The term haloalkylsulfonyl denotes a haloalkyl group, as defined above, attached via a sulfonyl [S(O).sub.2] group to the remainder of the molecule. C.sub.1-C.sub.2-Haloalkylsulfonyl is, for example, S(O).sub.2CH.sub.2F, S(O).sub.2CHF.sub.2, S(O).sub.2CF.sub.3, S(O).sub.2CH.sub.2Cl, S(O).sub.2CHCl.sub.2, S(O).sub.2CCl.sub.3, chlorofluoromethylsulfonyl, dichlorofluoromethylsulfonyl, chlorodifluoromethylsulfonyl, 2-fluoroethylsulfonyl, 2-chloroethylsulfonyl, 2-bromoethylsulfonyl, 2-iodoethylsulfonyl, 2,2-difluoroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, 2-chloro-2-fluoroethylsulfonyl, 2-chloro-2,2-difluoroethylsulfonyl, 2,2-dichloro-2-fluoroethylsulfonyl, 2,2,2-trichloroethylsulfonyl or S(O).sub.2C.sub.2F.sub.5. C.sub.1-C.sub.3-Haloalkylsulfonyl is additionally, for example, 2-fluoropropylsulfonyl, 3-fluoropropylsulfonyl, 2,2-difluoropropylsulfonyl, 2,3-difluoropropylsulfonyl, 2-chloropropylsulfonyl, 3-chloropropylsulfonyl, 2,3-dichloropropylsulfonyl, 2-bromopropylsulfonyl, 3-bromopropylsulfonyl, 3,3,3-trifluoropropylsulfonyl, 3,3,3-trichloropropylsulfonyl, S(O).sub.2CH.sub.2-C.sub.2F.sub.5, S(O).sub.2CF.sub.2-C.sub.2F.sub.5, 1-(CH.sub.2F)-2-fluoroethylsulfonyl, 1-(CH.sub.2Cl)-2-chloroethylsulfonylor 1-(CH.sub.2Br)-2-bromoethylsulfonyl. C.sub.1-C.sub.4-Haloalkylsulfonyl is additionally, for example, 4-fluorobutylsulfonyl, 4-chlorobutylsulfonyl, 4-bromobutylsulfonyl or nonafluorobutylsulfonyl. C.sub.1-C.sub.6-Haloalkylsulfonyl is additionally, for example, 5-fluoropentylsulfonyl, 5-chloropentylsulfonyl, 5-brompentylsulfonyl, 5-iodopentylsulfonyl, undecafluoropentylsulfonyl, 6-fluorohexylsulfonyl, 6-chlorohexylsulfonyl, 6-bromohexylsulfonyl, 6-iodohexylsulfonyl or dodecafluorohexylsulfonyl.
[0085] The substituent oxo replaces a CH.sub.2 group by a C(O) group.
[0086] The suffix -carbonyl in a group denotes in each case that the group is bound to the remainder of the molecule via a carbonyl CO group. This is the case e.g. in alkylcarbonyl, haloalkylcarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkoxycarbonyl, haloalkoxycarbonyl.
[0087] The term alkoxycarbonyl denotes an alkoxy group, as defined above, attached via a carbonyl [C(O)] group to the remainder of the molecule. C.sub.1-C.sub.3-Alkoxycarbonyl is a C.sub.1-C.sub.3-alkoxy group, as defined above, attached via a carbonyl [C(O)] group to the remainder of the molecule. Examples for C.sub.1-C.sub.3-alkoxycarbonyl are methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl and isopropoxycarbonyl. C.sub.1-C.sub.6-Alkoxycarbonyl is a C.sub.1-C.sub.6-alkoxy group, as defined above, attached via a carbonyl [C(O)] group to the remainder of the molecule. Examples for C.sub.1-C.sub.6-alkoxycarbonyl are, in addition to those listed for C.sub.1-C.sub.3-alkoxycarbonyl, n-butoxycarbonyl, sec-butoxycarbonyl, isobutoxycarbonyl, tert-butoxycarbonyl, pentoxycarbonyl and hexoxycarbonyl.
[0088] The term haloalkoxycarbonyl denotes a haloalkoxy group, as defined above, attached via a carbonyl [C(O)] group to the remainder of the molecule. C.sub.1-C.sub.3-Halolkoxycarbonyl is a C.sub.1-C.sub.3-haloalkoxy group, as defined above, attached via a carbonyl [C(O)] group to the remainder of the molecule. Examples for C.sub.1-C.sub.3-haloalkoxycarbonyl are C(O)OCH.sub.2F, C(O)OCHF.sub.2, C(O)OCF.sub.3, C(O)OCH.sub.2Cl, C(O) OCHCl.sub.2, C(O) OCCl.sub.3, chlorofluoromethoxycarbonyl, dichlorofluoromethoxycarbonyl, chlorodifluoromethoxycarbonyl, 2-fluoroethoxycarbonyl, 2-chloroethoxycarbonyl, 2-bromoethoxycarbonyl, 2-iodoethoxycarbonyl, 2,2-difluoroethoxycarbonyl, 2,2,2-trifluoroethoxycarbonyl, 2-chloro-2-fluoroethoxycarbonyl, 2-chloro-2,2-difluoroethoxycarbonyl, 2,2-dichloro-2-fluoroethoxycarbonyl, 2,2,2-trichloroethoxycarbonyl, C(O) OC.sub.2F.sub.5, 2-fluoropropoxycarbonyl, 3-fluoropropoxycarbonyl, 2,2-difluoropropoxycarbonyl, 2,3-difluoropropoxycarbonyl, 2-chloropropoxycarbonyl, 3-chloropropoxycarbonyl, 2,3-dichloropropoxycarbonyl, 2-bromopropoxycarbonyl, 3-bromopropoxycarbonyl, 3,3,3-trifluoropropoxycarbonyl, 3,3,3-trichloropropoxycarbonyl, C(O)OCH.sub.2-C.sub.2F.sub.5, C(O)OCF.sub.2-C.sub.2F.sub.5, 1-(CH.sub.2F)-2-fluoroethoxycarbonyl, 1-(CH.sub.2Cl)-2-chloroethoxycarbonyl or 1-(CH.sub.2Br)-2-bromoethoxycarbonyl.
[0089] The term alkoxycarbonyl-alkyl denotes an alkyl group, as defined above, in which one hydrogen atom is replaced by an alkoxycarbonyl group, as defined above. C.sub.1-C.sub.6-Alkoxycarbonyl-C.sub.1-C.sub.6-alkyl is a C.sub.1-C.sub.6-alkyl group, as defined above, in which one hydrogen atom is replaced by a C.sub.1-C.sub.6-alkoxycarbonyl group, as defined above.
[0090] Phenyl-(C.sub.1-C.sub.3-alkyl) is a C.sub.1-C.sub.3-alkyl group, as defined above, in which one hydrogen atom is replaced by a phenyl ring (i.e. the attachment to the remainder of the molecule is via the alkyl group). Examples are benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylpropyl, 2-phenylpropyl, 3-phenylpropyl or 2-phenyl-2-propyl.
[0091] Furanyl-(C.sub.1-C.sub.3-alkyl) is a C.sub.1-C.sub.3-alkyl group, as defined above, in which one hydrogen atom is replaced by a 2- or 3-furanyl ring (i.e. the attachment to the remainder of the molecule is via the alkyl group). Examples are furan-2-yl-methyl, furan-3-yl-methyl, 1-(furan-2-yl)-ethyl, 1-(furan-3-yl)-ethyl, 2-(furan-2-yl)-ethyl, 2-(furan-3-yl)-ethyl and the like.
[0092] Phenylthio is a phenyl ring attached via an S atom to the remainder of the molecule.
[0093] Phenylsulfinyl is a phenyl ring attached via a S(O) group to the remainder of the molecule.
[0094] Phenylsulfonyl is a phenyl ring attached via a S(O).sub.2 group to the remainder of the molecule.
[0095] Z is a three-, four-, five- or six-membered saturated, partly unsaturated, fully unsaturated or aromatic ring, except phenyl, which is formed from r carbon atoms, n nitrogen atoms, n sulfur atoms and n oxygen atoms. The ring can thus be carbocyclic (i.e. containing only carbon atoms as ring members; r being here 3 to 6 and n being 0) or heterocyclic (i.e. containing also at least one N, O and/or S atom as ring member(s); r being here thus from 1 to 5 and at least one of the n's being 1).
[0096] An unsaturated carbocycle contains at least one CC double bond(s). An unsaturated heterocycle contains at least one CC and/or CN and/or NN double bond(s). Partially unsaturated carbocyclic rings contain less than the maximum number of CC double bond(s) allowed by the ring size. Partially unsaturated heterocyclic rings contain less than the maximum number of CC and/or CN and/or NN double bond(s) allowed by the ring size. A fully (or maximally) unsaturated carbocyclic ring contains as many conjugated CC double bonds as allowed by the size(s) of the ring(s). Not encompassed in the definition of Z is however phenyl. A fully (or maximally) unsaturated heterocycle contains as many conjugated CC and/or CN and/or NN double bonds as allowed by the size(s) of the ring(s). Maximally unsaturated 5- or 6-membered heteromonocyclic rings are generally aromatic. Exceptions are maximally unsaturated 6-membered rings containing O, S, SO and/or SO.sub.2 as ring members, such as pyran and thiopyran, which are not aromatic.
[0097] Examples for three-, four-, five- or six-membered saturated, partly unsaturated, fully unsaturated or aromatic carbocyclic rings Z are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloprop-1-enyl, cycloprop-2-enyl, cyclobut-1-enyl, cyclobut-2-enyl, cyclobutadienyl, cyclopent-1-enyl, cyclopent-2-enyl, cyclopent-3-enyl, cyclopenta-1,3-dienyl, cyclopenta-1,4-dienyl, cyclopenta-2,4-dienyl, cyclohex-1-enyl, cyclohex-2-enyl, cyclohex-3-enyl, cyclohexa-1,3-dienyl, cyclohexa-1,4-dienyl, cyclohexa-1,5-dienyl, cyclohexa-2,4-dienyl, cyclohexa-2,5-dienyl, and the like.
[0098] Examples for three-, four-, five- or six-membered saturated, partly unsaturated, fully unsaturated or aromatic heterocyclic rings Z are:
[0099] 3-, 4-, 5- or 6-membered monocyclic saturated heterocycle: e.g. oxiran-2-yl, thiiran-2-yl, aziridin-1-yl, aziridin-2-yl, oxetan-2-yl, oxetan-3-yl, thietan-2-yl, thietan-3-yl, 1-oxothietan-2-yl, 1-oxothietan-3-yl, 1,1-dioxothietan-2-yl, 1,1-dioxothietan-3-yl, azetidin-1-yl, azetidin-2-yl, azetidin-3-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydrothien-2-yl, tetrahydrothien-3-yl, 1-oxotetrahydrothien-2-yl, 1,1-dioxotetrahydrothien-2-yl, 1-oxotetrahydrothien-3-yl, 1,1-dioxotetrahydrothien-3-yl, 1,3-dioxolan-2-yl, 1,3-dioxolan-4-yl, 1,3-ditholan-2-yl, 1,3-ditholan-4-yl, 1,3-oxathiolan-2-yl, 1,3-oxathiolan-4-yl, 1,3-oxathiolan-5-yl, pyrrolidin-1-yl, pyrrolidin-2-yl, pyrrolidin-3-yl, pyrazolidin-1-yl, pyrazolidin-3-yl, pyrazolidin-4-yl, pyrazolidin-5-yl, imidazolidin-1-yl, imidazolidin-2-yl, imidazolidin-4-yl, oxazolidin-2-yl, oxazolidin-3-yl, oxazolidin-4-yl, oxazolidin-5-yl, isoxazolidin-2-yl, isoxazolidin-3-yl, isoxazolidin-4-yl, isoxazolidin-5-yl, thiazolidin-2-yl, thiazolidin-3-yl, thiazolidin-4-yl, thiazolidin-5-yl, isothiazolidin-2-yl, isothiazolidin-3-yl, isothiazolidin-4-yl, isothiazolidin-5-yl, 1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl, 1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl, 1,3,4-oxadiazolidin-2-yl, 1,3,4-thiadiazolidin-2-yl, 2-tetrahydropyranyl, 3-tetrahydropyranyl, 4-tetrahydropyranyl, 1,3-dioxan-2-yl, 1,3-dioxan-4-yl, 1,3-dioxan-5-yl, 1,4-dioxan-2-yl, piperidin-1-yl, piperidin-2-yl, piperidin-3-yl, piperidin-4-yl, hexahydropyridazin-1-yl, hexahydropyridazin-3-yl, hexahydropyridazin-4-yl, hexahydropyrimidin-1-yl, hexahydropyrimidin-2-yl, hexahydropyrimidin-4-yl, hexahydropyrimidin-5-yl, piperazin-1-yl, piperazin-2-yl, morpholin-2-yl, morpholin-3-yl, morpholin-4-yl, thiomorpholin-2-yl, thiomorpholin-3-yl, thiomorpholin-4-yl, 1-oxothiomorpholin-2-yl, 1 oxothiomorpholin-3-yl, 1-oxothiomorpholin-4-yl, 1,1 dioxothiomorpholin-2-yl, 1,1 dioxothiomorpholin-3-yl, 1,1-dioxothiomorpholin-4-yl, and the like;
[0100] 5- or 6-membered monocyclic partially unsaturated heterocycles: e.g. 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,5-dihydrofur-2-yl, 2,5-dihydrofur-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,5-dihydrothien-2-yl, 2,5-dihydrothien-3-yl, 2-pyrrolin-2-yl, 2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin-3-yl, 2-isoxazolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl, 2-isoxazolin-5-yl, 3-isoxazolin-5-yl, 4-isoxazolin-5-yl, 2-isothiazolin-3-yl, 3-isothiazolin-3-yl, 4-isothiazolin-3-yl, 2-isothiazolin-4-yl, 3-isothiazolin-4-yl, 4-isothiazolin-4-yl, 2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl, 2,3-dihydropyrazol-1-yl, 2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1-yl, 3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl, 3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-1-yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,6-dihydro-2H-pyran-2-, -3-, -4-, -5- or 6-yl, 3,4-dihydro-2H-pyran-2-, -3-, -4-, -5- or 6-yl, 3,6-dihydro-2H-thiopyran-2-, -3-, -4-, -5- or 6-yl, 3,4-dihydro-2H-thiopyran-2-, -3-, -4-, -5- or 6-yl, 2-, 3-, 4-, 5- or 6-di- or tetrahydropyridinyl, 3-di- or tetrahydropyridazinyl, 4-di- or tetrahydropyridazinyl, 2-di- or tetrahydropyrimidinyl, 4-di- or tetrahydropyrimidinyl, 5-di- or tetrahydropyrimidinyl, di- or tetrahydropyrazinyl;
[0101] 5- or 6-membered monocyclic fully unsaturated (including aromatic) heterocyclic ring: e.g. 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 1-pyrazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 1-imidazolyl, 2-imidazolyl, 4-imidazolyl, 5-imidazolyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl and 2-pyrazinyl.
[0102] Specifically, Z is a five- or six-membered partly unsaturated carbocyclic ring. Examples therefor are cyclopent-1-en-1-yl, cyclopent-2-en-1-yl, cyclopent-3-en-1-yl, cyclopenta-1,3-dien-1-yl, cyclopenta-1,4-dien-1-yl, cyclopenta-2,4-dien-1-yl, cyclohex-1-en-1-yl, cyclohex-2-en-1-yl, cyclohex-3-en-1-yl, cyclohexa-1,3-dien-1-yl, cyclohexa-1,4-dien-1-yl, cyclohexa-1,5-dien-1-yl, cyclohexa-2,4-dien-1-yl and cyclohexa-2,5-dien-1-yl.
[0103] If two radicals bound on the same nitrogen atom (for example R.sup.b2 and R.sup.b3), together with the nitrogen atom to which they are bound, form a 3-, 4-, 5-, 6- or 7-membered, saturated N-bound heterocyclic ring which may contain as a ring member a further heteroatom or heteroatom group selected from the group consisting of N, O, S, S(O) and S(O).sub.2, this is for example aziridn-1-yl, azetidin-1-yl, pyrrolidin-1-yl, pyrazolidin-1-yl, imidazolidin-1-yl, oxazolidin-3-yl, thiazolidin-3-yl, isoxazolidin-2-yl, isothiazolin-2-yl, piperdin-1-yl, piperazin-1-yl, morpholin-1-yl, thiomorpholin-1-yl, 1-oxothiomorpholin-1-yl, 1,1-dioxothiomorpholin-1-yl, azepan-1-yl or 1,4-diazepan-1-yl.
[0104] If two radicals bound on the same nitrogen atom (for example R.sup.b2 and R.sup.b3), together with the nitrogen atom to which they are bound, form a 5- or 6-membered, saturated N-bound heterocyclic ring, this is pyrrolidin-1-yl or piperidin-1-yl.
[0105] The remarks made below as to preferred embodiments of the variables (substituents) of the compounds of formula I are valid on their own as well as preferably in combination with each other, as well as in combination with the stereoisomers or salts thereof. The remarks made below concerning preferred embodiments of the variables further are valid on their own as well as preferably in combination with each other concerning the compounds of formulae I, where applicable, as well as concerning the uses and methods according to the invention and the composition according to the invention.
[0106] Preferably, R.sup.1 is hydrogen or (C.sub.1-C.sub.3)-alkyl, and is more preferably hydrogen.
[0107] Preferably, R.sup.9 is hydrogen or (C.sub.1-C.sub.3)-alkyl, and is more preferably hydrogen.
[0108] Preferably, R.sup.1 and R.sup.9 are both hydrogen.
[0109] Preferably, R.sup.2 is hydrogen, halogen or (C.sub.1-C.sub.3)-alkyl. More preferably, R.sup.2 is hydrogen or halogen. In particular, R.sup.2 is hydrogen.
[0110] Preferably, R.sup.6 is hydrogen, halogen or (C.sub.1-C.sub.3)-alkyl. More preferably, R.sup.6 is hydrogen.
[0111] Preferably, R.sup.2 and R.sup.6, independently of each other, are hydrogen, halogen or (C.sub.1-C.sub.3)alkyl. More preferably, R.sup.2 is hydrogen or halogen and R.sup.6 is hydrogen. In particular, R.sup.2 is hydrogen and R.sup.6 is hydrogen.
[0112] Preferably, R.sup.3 is hydrogen, halogen, (C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-haloalkyl, (C.sub.1-C.sub.3)-alkoxy or
[0113] (C.sub.1-C.sub.3)-haloalkoxy. More preferably, R.sup.3 is hydrogen, halogen, (C.sub.1-C.sub.2)-alkyl, (C.sub.1-C.sub.2)-haloalkyl, (C.sub.1-C.sub.2)-alkoxy or (C.sub.1-C.sub.2)-haloalkoxy. Even more preferably, R.sup.3 is halogen, (C.sub.1-C.sub.2)-alkyl, (C.sub.1-C.sub.2)-haloalkyl, (C.sub.1-C.sub.2)-alkoxy or (C.sub.1-C.sub.2)-haloalkoxy. In particular, R.sup.3 is halogen, (C.sub.1-C.sub.2)-alkyl or (C.sub.1-C.sub.2)-haloalkoxy. Specifically, R.sup.3 is hydrogen or halogen.
[0114] Preferably, R.sup.5 is hydrogen, halogen, (C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-haloalkyl, (C.sub.1-C.sub.3)-alkoxy or (C.sub.1-C.sub.3)-haloalkoxy. More preferably, R.sup.5 is hydrogen, halogen or (C.sub.1-C.sub.2)-alkyl. Specifically, R.sup.5 is hydrogen or halogen.
[0115] Preferably R.sup.3 and R.sup.5, independently of each other, are hydrogen, halogen, (C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-haloalkyl, (C.sub.1-C.sub.3)-alkoxy or (C.sub.1-C.sub.3)-haloalkoxy. More preferably, R.sup.3 is hydrogen, halogen, (C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-haloalkyl, (C.sub.1-C.sub.3)-alkoxy or (C.sub.1-C.sub.3)-haloalkoxy and R.sup.5 is hydrogen, halogen or (C.sub.1-C.sub.2)-alkyl. Even more preferably, R.sup.3 is halogen, (C.sub.1-C.sub.3)-alkyl or (C.sub.1-C.sub.3)-haloalkoxy and R.sup.5 is hydrogen or halogen. In particular, R.sup.3 and R.sup.5, independently of each other, are hydrogen or halogen.
[0116] Preferably, R.sup.4 is hydrogen or halogen. In particular, R.sup.4 is hydrogen.
[0117] Preferably, R.sup.7 and R.sup.8, independently of each other, are (C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.2-C.sub.6)-alkenyl or (C.sub.2-C.sub.6)-alkynyl, each substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl and cyano. Preferably, m is 0, 1 or 2, more preferably, 0 or 1 and specifically 0. Thus, more preferably, R.sup.7 and R.sup.8, independently of each other, are (in each case unsubstituted) (C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.2-C.sub.6)-alkenyl or (C.sub.2-C.sub.6)-alkynyl. Even more preferably, R.sup.7 and R.sup.8, independently of each other, are (C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl or (C.sub.2-C.sub.6)-alkenyl. In particular, R.sup.7 and R.sup.8, independently of each other, are (C.sub.1-C.sub.6)-alkyl or (C.sub.2-C.sub.6)-alkenyl; more particularly (C.sub.1-C.sub.6)-alkyl; even more particularly (C.sub.1-C.sub.4)-alkyl, specifically methyl or ethyl, and are very specifically both methyl.
[0118] In the divalent radicals (X.sup.1) to (X.sup.6), the orientation within the molecule is as depicted, the left arrow representing the bond to the adjacent nitrogen atom and the right arrow representing the bond to Y.
[0119] When X is a bond (X.sup.0), the compound (I) can also be depicted as follows:
##STR00004##
[0120] When X is a divalent radical of the formula (X.sup.1), the compound (I) can also be depicted as follows:
##STR00005##
[0121] When X is a divalent radical of the formula (X.sup.2), the compound (I) can also be depicted as follows:
##STR00006##
[0122] When X is a divalent radical of the formula (X.sup.3), the compound (I) can also be depicted as follows:
##STR00007##
[0123] When X is a divalent radical of the formula (X.sup.4), the compound (I) can also be depicted as follows:
##STR00008##
[0124] When X is a divalent radical of the formula (X.sup.5), the compound (I) can also be depicted as follows:
##STR00009##
[0125] When X is a divalent radical of the formula (X.sup.6), the compound (I) can also be depicted as follows:
##STR00010##
[0126] In the divalent radicals (X.sup.1) to (X.sup.6), R.sup.10-R.sup.15, independently of each other and independently of each occurrence, are preferably selected from the group consisting of hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, CO.sub.2R.sup.e, CONR.sup.bR.sup.d; (C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.5)-cycloalkyl, (C.sub.2-C.sub.6)-alkenyl, where the three last-mentioned aliphatic and cycloaliphatic radicals are each independently substituted by m fluorine atoms; (C.sub.1-C.sub.6)-alkoxy, (C.sub.3-C.sub.6)-cycloalkoxy, (C.sub.2-C.sub.6)-alkenyloxy, (C.sub.2-C.sub.6)-alkynyloxy, (C.sub.1-C.sub.3)-alkylsulfinyl, (C.sub.1-C.sub.3)-alkylsulfonyl and (C.sub.1-C.sub.3)-alkylthio, where the aliphatic and cycloaliphatic moieties in the 7 last-mentioned radicals are each independently substituted by m fluorine atoms.
[0127] More preferably, R.sup.10-R.sup.15, independently of each other and independently of each occurrence, are selected from the group consisting of hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, CO.sub.2R.sup.e, CONR.sup.bR.sup.d; (C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.5)-cycloalkyl, (C.sub.2-C.sub.6)-alkenyl, where the three last-mentioned aliphatic and cycloaliphatic radicals are each independently substituted by m fluorine atoms; (C.sub.1-C.sub.6)-alkoxy, (C.sub.3-C.sub.6)-cycloalkoxy, (C.sub.2-C.sub.6)-alkenyloxy or (C.sub.2-C.sub.6)-alkynyloxy, where the aliphatic and cycloaliphatic moieties in the four last-mentioned radicals are each independently substituted by m fluorine atoms.
[0128] In particular, R.sup.10-R.sup.15, independently of each other and independently of each occurrence, are selected from the group consisting of hydrogen, fluorine, chlorine, CO.sub.2R.sup.e, CONR.sup.bR.sup.d, (C.sub.1-C.sub.6)-alkyl substituted by m fluorine atoms, or (C.sub.1-C.sub.6)-alkoxy substituted by m fluorine atoms.
[0129] In particular, R.sup.10-R.sup.15, independently of each other and independently of each occurrence, are selected from the group consisting of hydrogen, halogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.3)-alkoxy, and CO.sub.2R.sup.e. More particularly, R.sup.10-R.sup.15, independently of each other and independently of each occurrence, are hydrogen or (C.sub.1-C.sub.6)-alkyl and specifically hydrogen or methyl.
[0130] Non-exhaustive examples for suitable divalent radicals (X.sup.1) to (X.sup.6) are CH.sub.2, CH.sub.2CH.sub.2, CH(CH.sub.3), CH.sub.2CH.sub.2CH.sub.2, CH(CH.sub.2CH.sub.3), CH(CH.sub.3) CH.sub.2, C(CH.sub.3) 2, C(CH.sub.3) 2CH.sub.2, C(iPr)CH.sub.3, CH(CH.sub.2iPr) CH.sub.2, CH.sub.2CHCH, C(CH.sub.3) 2CC, CH(CF.sub.3) CH.sub.2, CH(CH.sub.3) CH.sub.2O, CH.sub.2CH.sub.2O, CH(cPr) CH.sub.2O, CH(CH.sub.2OCH.sub.3), CH(CH.sub.2CH.sub.2SCH.sub.3), CH(COOH), CH(COOCH.sub.3), CH(COOH) CH.sub.2, CH(COOCH.sub.3) CH.sub.2, CH.sub.2C(OH) (CF.sub.3), CH(CONHCH.sub.3), CH(CONHCH.sub.3) CH.sub.2 and CH.sub.2CH.sub.2CONHCH.sub.2, cPr is cyclopropyl; iPr is isopropyl.
[0131] In a preferred embodiment, X is a bond or the divalent unit (X.sup.1). In the latter, preferably, R.sup.10 and R.sup.11, independently of each other, are hydrogen or (C.sub.1-C.sub.6)-alkyl, and more preferably hydrogen or methyl. In particular, one of R.sup.10 and R.sup.11 is hydrogen and the other is methyl, X.sup.1 thus being in particular CH(CH.sub.3).
[0132] In a preferred embodiment, Y is Z.
[0133] Z is preferably a three-, four-, five- or six-membered saturated, partly unsaturated or fully unsaturated carbocyclic ring, except phenyl, which is substituted by p radicals selected from the group consisting of CO.sub.2R.sup.e, CONR.sup.bR.sup.h, S(O), R.sup.a, SO.sub.2NR.sup.bR.sup.d, SO.sub.2NR.sup.bCOR.sup.e, CORD, CONR.sup.eS(O)R.sup.a, CONR.sup.eSO.sub.2R.sup.a, CONR.sup.b1SO.sub.2NR.sup.b2R.sup.b3, NR.sup.bR.sup.e, NR.sup.bCOR.sup.e, NRbCONR.sup.eR.sup.e, NR.sup.bCO.sub.2R.sup.e, NR.sup.bSO.sub.2R.sup.e, NR.sup.b1SO.sub.2NR.sup.b2R.sup.e, OCONR.sup.bR.sup.e, OCSNR.sup.bR.sup.e, POR.sup.fR.sup.f and C(R.sup.b)NOR.sup.e, and more preferably by p radicals selected from the group consisting of CO.sub.2R.sup.e, CONR.sup.bR.sup.h and CONR.sup.eS(O)R.sup.a; and where the carbon ring atoms bear n oxo groups. p is in this context preferably 1 or 2, more preferably 1. n is in this context preferably 0 or 1, in particular 0. More preferably, Z is a five- or sixmembered saturated or partly unsaturated carbocyclic ring which is substituted by p radicals selected from the group consisting of CO.sub.2R.sup.e, CONR.sup.bR.sup.h and CONR.sup.eS(O)R.sup.a. In particular, Z is a five- or six-membered saturated or partly unsaturated carbocyclic ring which is substituted by p radicals CO.sub.2R.sup.e. R.sup.e is in this context preferably hydrogen, (C.sub.1 -C.sub.6)-alkyl or (C.sub.3-C.sub.6)-cycloalkyl; specifically hydrogen or (C.sub.1-C.sub.6)-alkyl, and p is in this context preferably 1 or 2, more preferably 1. Thus, more particularly, Z is a five- or sixmembered saturated or partly unsaturated carbocyclic ring which is substituted by p radicals CO.sub.2R.sup.e, where R.sup.e is hydrogen, (C.sub.1-C.sub.6)-alkyl or (C.sub.3-C.sub.6)-cycloalkyl; specifically hydrogen or (C.sub.1-C.sub.6)-alkyl, more specifically hydrogen or (C.sub.1-C.sub.4)-alkyl, very specifically hydrogen or methyl, and p is 1 or 2, preferably 1. Even more particularly, Z is a five- or six-membered partly unsaturated carbocyclic ring which is substituted by p radicals CO.sub.2R.sup.e, where R.sup.e is hydrogen, (C.sub.1-C.sub.6)-alkyl or (C.sub.3-C.sub.6)-cycloalkyl; specifically hydrogen or (C.sub.1-C.sub.6)-alkyl, more specifically hydrogen or (C.sub.1-C.sub.4)-alkyl, very specifically hydrogen or methyl, and p is 1 or 2, preferably 1. Specifically, Z is a five-membered partly unsaturated carbocyclic ring which is substituted by p radicals CO.sub.2R.sup.e, where R.sup.e is hydrogen, (C.sub.1-C.sub.6)-alkyl or (C.sub.3-C.sub.6)-cycloalkyl; specifically hydrogen or (C.sub.1-C.sub.6)-alkyl, more specifically hydrogen or (C.sub.1-C.sub.4)-alkyl, very specifically hydrogen or methyl, and p is 1 or 2, preferably 1.
[0134] Examples for five- or six-membered saturated or partly unsaturated carbocyclic rings are listed above. Among these, preference is given to cyclopentyl, cyclopent-1-en-1-yl, cyclopent-2-en-1-yl, cyclopent-3-en-1-yl and cyclohexyl. A specific example is cyclopent-2-en-1-yl. In the latter ring, if p is 1, the mandatory substituent (CO.sub.2R.sup.e etc.) is preferably bound in the 4-position.
[0135] In an alternatively preferred embodiment, Z is a three-, four-, five- or six-membered saturated, partly unsaturated or fully unsaturated heterocyclic ring containing one or two oxygen atoms as ring members, where the ring is substituted by p radicals selected from the group consisting of CO.sub.2R.sup.e, CONR.sup.bR.sup.h, S(O), R.sup.a, SO.sub.2NR.sup.bR.sup.d, SO.sub.2NR.sup.bCOR.sup.e, CORD, CONR.sup.eS(O)R.sup.a, CONR.sup.eSO.sub.2R.sup.a, CONR.sup.b1SO.sub.2NR.sup.b2R.sup.b3, NR.sup.bR.sup.e, NR.sup.bCOR.sup.e, NR.sup.b- CONR.sup.eR.sup.e, NR.sup.bCO.sub.2R.sup.e, NR.sup.bSO.sub.2R.sup.e, NR.sup.b1SO.sub.2NR.sup.b2R.sup.e, OCONR.sup.bR.sup.e, OCSNR.sup.bR.sup.e, PORIRf and C(R.sup.b)NOR.sup.e, and where the carbon ring atoms bear n oxo groups. p is in this context preferably 1 or 2, more preferably 1. n is in this context preferably 0 or 1, in particular 0. More preferably, Z is a saturated or partly unsaturated five- or six-membered heterocyclic ring containing one oxygen atom as ring member, where the ring is substituted by p radicals CO.sub.2R.sup.e. R.sup.e is in this context preferably hydrogen, (C.sub.1-C.sub.6)-alkyl or (C.sub.3-C.sub.6)-cycloalkyl; specifically hydrogen or (C.sub.1-C.sub.6)-alkyl, and p is in this context preferably 1 or 2, more preferably 1. Thus, more particularly, Z is a saturated or partly unsaturated five- or six-membered heterocyclic ring containing one oxygen atom as ring member, where the ring is substituted by p radicals CO.sub.2R.sup.e, where R.sup.e is hydrogen, (C.sub.1-C.sub.6)-alkyl or (C.sub.3-C.sub.6)-cycloalkyl; specifically hydrogen or (C.sub.1-C.sub.6)-alkyl, and p is 1 or 2, preferably 1. Even more particularly, Z is a saturated or partly unsaturated five-membered heterocyclic ring containing one oxygen atom as ring member, where the ring is substituted by p radicals CO.sub.2R.sup.e, where R.sup.e is hydrogen or (C.sub.1-C.sub.6)-alkyl. and p is in this context preferably 1 or 2, more preferably 1. Specifically, Z is a saturated or partly unsaturated five-membered heterocyclic ring containing one oxygen atom as ring member, where the ring is substituted by one radical CO.sub.2R.sup.e, where R.sup.e is hydrogen or (C.sub.1-C.sub.6)-alkyl.
[0136] Examples for three-, four-, five- or six-membered saturated, partly unsaturated or fully unsaturated heterocyclic rings containing one or two oxygen atoms as ring members are oxiran-2-yl, oxetan-2-yl, oxetan-3-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, 1,3-dioxolan-2-yl, 1,3-dioxolan-4-yl, tetrahydropyran-2-yl, tetrahydropyran-3-yl, tetrahydropyran-4-yl, 1,3-dioxan-2-yl, 1,3-dioxan-4-yl, 1,3-dioxan-5-yl, 1,4-dioxan-2-yl, 2,3-dihydrofuran-2-yl, 2,3-dihydrofuran-3-yl, 2,5-dihydrofuran-2-yl, 2,5-dihydrofuran-3-yl, 3,6-dihydro-2H-pyran-2-yl, 3,6-dihydro-2H-pyran-3-yl, 3,6-dihydro-2H-pyran-4-yl, 3,6-dihydro-2H-pyran-5-yl, 3,6-dihydro-2H-pyran-6-yl, 3,4-dihydro-2H-pyran-2-yl, 3,4-dihydro-2H-pyran-3-yl, 3,4-dihydro-2H-pyran-4-yl, 3,4-dihydro-2H-pyran-5-yl or 3,4-dihydro-2H-pyran-6-yl.
[0137] Examples for saturated or partly unsaturated five- or six-membered heterocyclic rings containing one oxygen atom as ring member are tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydropyran-2-yl, tetrahydropyran-3-yl, tetrahydropyran-4-yl, 2,3-dihydrofuran-2-yl, 2,3-dihydrofuran-3-yl, 2,5-dihydrofuran-2-yl, 2,5-dihydrofuran-3-yl, 3,6-dihydro-2Hpyran-2-yl, 3,6-dihydro-2H-pyran-3-yl, 3,6-dihydro-2H-pyran-4-yl, 3,6-dihydro-2Hpyran-5-yl, 3,6-dihydro-2H-pyran-6-yl, 3,4-dihydro-2H-pyran-2-yl, 3,4-dihydro-2Hpyran-3-yl, 3,4-dihydro-2H-pyran-4-yl, 3,4-dihydro-2H-pyran-5-yl or 3,4-dihydro-2Hpyran-6-yl.
[0138] Examples for saturated or partly unsaturated five-membered heterocyclic rings containing one oxygen atom as ring member are tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, 2,3-dihydrofuran-2-yl, 2,3-dihydrofuran-3-yl, 2,5-dihydrofuran-2-yl, or 2,5-dihydrofuran-3-yl.
[0139] Preferably, however, ring Z is carbocyclic.
[0140] In another preferred embodiment, Y is (C.sub.1-C.sub.8)-alkyl which is substituted by p radicals selected from the group consisting of CO.sub.2R.sup.e, CONR.sup.bR.sup.h, S(O), R.sup.a, SO.sub.2NR.sup.bR.sup.d, SO.sub.2NR.sup.bCOR.sup.e, CORD, CONR.sup.eS(O)R.sup.a, CONR.sup.eSO.sub.2R.sup.a, CONR.sup.b1SO.sub.2NR.sup.b2R.sup.b3, NR.sup.bR.sup.e, NR.sup.bCOR.sup.e, NRbCONR.sup.eR.sup.e, NR.sup.bCO.sub.2R.sup.e, NR.sup.bSO.sub.2R.sup.e, NR.sup.b1SO.sub.2NR.sup.b2R.sup.e, OCONR.sup.bR.sup.e, OCSNR.sup.bR.sup.e, POR.sup.fR.sup.f and C(R.sup.b)NOR.sup.e. p is in this context preferably 1 or 2, more preferably 1.
[0141] More preferably, Y is (C.sub.1-C.sub.4)-alkyl which is substituted by p radicals selected from the group consisting of CO.sub.2R.sup.e, CONR.sup.bR.sup.h, CONR.sup.eS(O)R.sup.a, CONR.sup.eSO.sub.2R.sup.a and
[0142] CONR.sup.b1SO.sub.2NR.sup.b2R.sup.b3, where R.sup.a, R.sup.b, R.sup.b1, R.sup.b2, R.sup.b3, R.sup.e and R.sup.h are as defined above, where however in particular: [0143] R.sup.e in CO.sub.2R.sup.e is hydrogen, (C.sub.1-C.sub.6)-alkyl which may carry a cyano substituent; (C.sub.3-C.sub.6)-cycloalkyl; (C.sub.2-C.sub.4)-alkynyl; or phenyl-(C.sub.1-C.sub.3)-alkyl; preferably (C.sub.1-C.sub.6)-alkyl or (C.sub.3-C.sub.6)-cycloalkyl; specifically hydrogen or (C.sub.1-C.sub.6)-alkyl, more specifically hydrogen or (C.sub.1-C.sub.4)-alkyl, very specifically hydrogen or methyl; [0144] R.sup.b in CONR.sup.bR.sup.h is hydrogen or (C.sub.1-C.sub.3)-alkyl; [0145] R.sup.h in CONR.sup.bR.sup.h is (C.sub.1-C.sub.3)-alkoxy; [0146] R.sup.e in CONR.sup.eS(O)R.sup.a is hydrogen or (C.sub.1-C.sub.3)-alkyl; [0147] R.sup.a in CONR.sup.eS(O)R.sup.a is (C.sub.1-C.sub.6)-alkyl or (C.sub.1-C.sub.3)-haloalkyl; [0148] R.sup.e in CONR.sup.eSO.sub.2R.sup.a is hydrogen or (C.sub.1-C.sub.3)-alkyl; [0149] R.sup.a in CONR.sup.eSO.sub.2R.sup.a is (C.sub.1-C.sub.6)-alkyl or (C.sub.1-C.sub.3)-haloalkyl; [0150] R.sup.b1 in CONR.sup.b1SO.sub.2NR.sup.b2R.sup.b3 is hydrogen or (C.sub.1-C.sub.3)-alkyl; [0151] R.sup.b2 in CONR.sup.b1SO.sub.2NR.sup.b2R.sup.b3 is hydrogen or (C.sub.1-C.sub.3)-alkyl; [0152] R.sup.b3 in CONR.sup.b1SO.sub.2NR.sup.b2R.sup.b3 is (C.sub.1-C.sub.6)-alkyl; or [0153] R.sup.b2 and R.sup.b3, together with the nitrogen atom they are bound to, form a saturated 5- or 6-membered N-bound heterocyclic ring; and [0154] p is 1 or 2, preferably 1.
[0155] In a preferred embodiment, X is a bond and Y is Z, where Z has one of the above general or preferred meanings.
[0156] Preferably, Z is a three-, four-, five- or six-membered saturated, partly unsaturated or fully unsaturated carbocyclic ring, except phenyl, which is substituted by p radicals selected from the group consisting of CO.sub.2R.sup.e, CONR.sup.bR.sup.h, S(O), R.sup.a, SO.sub.2NR.sup.bR.sup.d, SO.sub.2NR.sup.bCOR.sup.e, CORD, CONR.sup.eS(O)R.sup.a, CONR.sup.eSO.sub.2R.sup.a, CONR.sup.b1SO.sub.2NR.sup.b2R.sup.b3, NR.sup.bR.sup.e, NR.sup.bCOR.sup.e, NRbCONR.sup.eR.sup.e, NR.sup.bCO.sub.2R.sup.e, NR.sup.bSO.sub.2R.sup.e, NR.sup.b1SO.sub.2NR.sup.b2R.sup.e, OCONR.sup.bR.sup.e, OCSNR.sup.bR.sup.e, POR.sup.fR.sup.f and C(R.sup.b)NOR.sup.e, and where the carbon ring atoms bear n oxo groups. p is in this context preferably 1 or 2, more preferably 1. n is in this context preferably 0 or 1, in particular 0.
[0157] More preferably, Z is a five- or six-membered saturated or partly unsaturated carbocyclic ring which is substituted by p radicals selected from the group consisting of CO.sub.2R.sup.e, CONR.sup.bR.sup.h and CONR.sup.eS(O)R.sup.a. In particular, Z is a five- or six-membered saturated or partly unsaturated carbocyclic ring which is substituted by p radicals CO.sub.2R.sup.e. R.sup.e is in this context preferably hydrogen, (C.sub.1-C.sub.6)-alkyl or (C.sub.3-C.sub.6)-cycloalkyl; specifically hydrogen or (C.sub.1-C.sub.6)-alkyl, more specifically hydrogen or (C.sub.1-C.sub.4)-alkyl, very specifically hydrogen or methyl, and p is in this context preferably 1 or 2, more preferably 1. Thus, particularly, Z is a five- or six-membered saturated or partly unsaturated carbocyclic ring which is substituted by p radicals CO.sub.2R.sup.e, where R.sup.e is hydrogen, (C.sub.1-C.sub.6)-alkyl or (C.sub.3-C.sub.6)-cycloalkyl; specifically hydrogen or (C.sub.1-C.sub.6)-alkyl, more specifically hydrogen or (C.sub.1-C.sub.4)-alkyl, very specifically hydrogen or methyl, and p is 1 or 2, preferably 1. More particularly, Z is a five- or six-membered partly unsaturated carbocyclic ring which is substituted by p radicals CO.sub.2R.sup.e, where R.sup.e is hydrogen, (C.sub.1-C.sub.6)-alkyl or (C.sub.3-C.sub.6)-cycloalkyl; specifically hydrogen or (C.sub.1-C.sub.6)-alkyl, more specifically hydrogen or (C.sub.1-C.sub.4)-alkyl, very specifically hydrogen or methyl, and p is 1 or 2, preferably 1. Specifically, Z is a five-membered partly unsaturated carbocyclic ring which is substituted by p radicals CO.sub.2R.sup.e, where R.sup.e is hydrogen or (C.sub.1-C.sub.6)-alkyl, specifically hydrogen or (C.sub.1-C.sub.4)-alkyl, very specifically hydrogen or methyl, and p is 1 or 2, preferably 1.
[0158] In an alternatively preferred embodiment, Z is a three-, four-, five- or six-membered saturated, partly unsaturated or fully unsaturated heterocyclic ring containing one or two oxygen atoms as ring members, where the ring is substituted by p radicals selected from the group consisting of CO.sub.2R.sup.e, CONR.sup.bR.sup.h, S(O),R.sup.a, SO.sub.2NR.sup.bR.sup.d, SO.sub.2NR.sup.bCOR.sup.e, CORD, CONR.sup.eS(O)R.sup.a, CONR.sup.eSO.sub.2R.sup.a, CONR.sup.b1SO.sub.2NR.sup.b2R.sup.b3, NR.sup.bR.sup.e, NR.sup.bCOR.sup.e, NR.sup.b- CONR.sup.eR.sup.e, NR.sup.bCO.sub.2R.sup.e, NR.sup.bSO.sub.2R.sup.e, NR.sup.b1SO.sub.2NR.sup.b2R.sup.e, OCONR.sup.bR.sup.e, OCSNR.sup.bR.sup.e, POR.sup.fR.sup.f and C(R.sup.b)NOR.sup.e, and where the carbon ring atoms bear n oxo groups. p is in this context preferably 1 or 2, more preferably 1. n is in this context preferably 0 or 1, in particular 0.
[0159] More preferably, Z is a saturated or partly unsaturated five- or six-membered heterocyclic ring containing one oxygen atom as ring member, where the ring is substituted by p radicals CO.sub.2R.sup.e. R.sup.e is in this context preferably hydrogen, (C.sub.1-C.sub.6)-alkyl or (C.sub.3-C.sub.6)-cycloalkyl; specifically hydrogen or (C.sub.1-C.sub.6)-alkyl, and p is in this context preferably 1 or 2, more preferably 1. Thus, particularly, Z is a saturated or partly unsaturated five- or six-membered heterocyclic ring containing one oxygen atom as ring member, where the ring is substituted by p radicals CO.sub.2R.sup.e, where R.sup.e is hydrogen, (C.sub.1-C.sub.6)-alkyl or (C.sub.3-C.sub.6)-cycloalkyl; specifically hydrogen or (C.sub.1-C.sub.6)-alkyl, and p is 1 or 2, preferably 1. More particularly, Z is a saturated or partly unsaturated five-membered heterocyclic ring containing one oxygen atom as ring member, where the ring is substituted by p radicals CO.sub.2R.sup.e, where R.sup.e is hydrogen or (C.sub.1-C.sub.6)-alkyl and p is 1 or 2, preferably 1.
[0160] Preferably, however, ring Z is carbocyclic.
[0161] In another preferred embodiment, [0162] X is a divalent unit (X.sup.1), where R.sup.10 and R.sup.11 are as defined above and are in particular independently hydrogen or (C.sub.1-C.sub.6)-alkyl; and [0163] Y is (C.sub.1-C.sub.8)-alkyl which is substituted by p radicals selected from the group consisting of CO.sub.2R.sup.e, CONR.sup.bR.sup.h, S(O),R.sup.a, SO.sub.2NR.sup.bR.sup.d, SO.sub.2NR.sup.bCOR.sup.e, COR.sup.b, CONR.sup.eS(O) R.sup.a, CONR.sup.eSO.sub.2R.sup.a, CONR.sup.b1SO.sub.2NR.sup.b2R.sup.b3, NR.sup.bR.sup.e, NR.sup.bCOR.sup.e, NR.sup.bCONR.sup.eR.sup.e, NR.sup.bCO.sub.2R.sup.e, NR.sup.bSO.sub.2R.sup.e, NR.sup.b1SO.sub.2NR.sup.b2R.sup.e, OCONR.sup.bR.sup.e, OCSNR.sup.bR.sup.e, POR.sup.fR.sup.f and C(R.sup.b)NOR.sup.e.
[0164] In an alternative preferred embodiment, [0165] X is a bond; and [0166] Y is (C.sub.1-C.sub.8)-alkyl which is substituted by p radicals selected from the group consisting of CO.sub.2R.sup.e, CONR.sup.bR.sup.h, S(O), R.sup.a, SO.sub.2NR.sup.bR.sup.d, SO.sub.2NR.sup.bCOR.sup.e, COR.sup.b, CONR.sup.eS(O) R.sup.a, CONR.sup.eSO.sub.2R.sup.a, CONR.sup.b1SO.sub.2NR.sup.b2R.sup.b3, NR.sup.bR.sup.e, NR.sup.bCOR.sup.e, NR.sup.bCONR.sup.eR.sup.e, NR.sup.bCO.sub.2R.sup.e, NR.sup.bSO.sub.2R.sup.e, NR.sup.b1SO.sub.2NR.sup.b2R.sup.e, OCONR.sup.bR.sup.e, OCSNR.sup.bR.sup.e, POR.sup.fR.sup.f and C(R.sup.b)NOR.sup.e.
[0167] More preferably, [0168] X is a divalent unit (X.sup.1), where R.sup.10 and R.sup.11 are independently hydrogen or methyl; and [0169] Y is (C.sub.1-C.sub.4)-alkyl which is substituted by p radicals selected from the group consisting of CO.sub.2R.sup.e, CONR.sup.bR.sup.h, CONR.sup.eS(O)R.sup.a, CONR.sup.eSO.sub.2R.sup.a and CONR.sup.b1SO.sub.2NR.sup.b2R.sup.b3, where R.sup.a, R.sup.b, R.sup.b1, R.sup.b2, R.sup.b3, R.sup.e and R.sup.h have one of the above general or preferred meanings.
[0170] In this context, Y is preferably (C.sub.1-C.sub.4)-alkyl which is substituted by p radicals CO.sub.2R.sup.e, where R.sup.e is hydrogen or (C.sub.1-C.sub.4)-alkyl, e.g. hydrogen or methyl; specifically (C.sub.1-C.sub.4)-alkyl, e.g. methyl.
[0171] In an alternative more preferred embodiment, [0172] X is a bond; and [0173] Y is (C.sub.1-C.sub.6)-alkyl which is substituted by p radicals selected from the group consisting of CO.sub.2R.sup.e, CONR.sup.bR.sup.h, CONR.sup.eS(O)R.sup.a, CONR.sup.eSO.sub.2R.sup.a and CONR.sup.b1SO.sub.2NR.sup.b2R.sup.b3, where R.sup.a, R.sup.b, R.sup.b1, R.sup.b2, R.sup.b3, R.sup.e and R.sup.h have one of the above general or preferred meanings.
[0174] In this latter alternative more preferred embodiment, (C.sub.1-C.sub.6)-alkyl in Y is preferably a group-C(R.sup.101) (R.sup.111)C.sub.1-C.sub.4-alkyl which is substituted by p radicals selected from the group consisting of CO.sub.2R.sup.e, CONR.sup.bR.sup.h, CONR.sup.eS(O)R.sup.a, CONR.sup.eSO.sub.2R.sup.a and CONR.sup.b1SO.sub.2NR.sup.b2R.sup.b3, where R.sup.a, R.sup.b, R.sup.b1, R.sup.b2, R.sup.b3, R.sup.e and R.sup.h have one of the above general or preferred meanings and R.sup.101 and R.sup.111 are independently hydrogen or methyl, where however preferably one of R.sup.101 and R.sup.111 is hydrogen and the other is methyl.
[0175] In this context, Y is preferably a group-C(R.sup.101) (R.sup.111)C.sub.1-C.sub.4-alkyl which is substituted by p radicals CO.sub.2R.sup.e, where R.sup.e is hydrogen or (C.sub.1-C.sub.4)-alkyl, e.g. hydrogen or methyl, specifically (C.sub.1-C.sub.4)-alkyl, e.g. methyl, and R.sup.101 and R.sup.111 are independently hydrogen or methyl, where however preferably one of R.sup.101 and R.sup.111 is hydrogen and the other is methyl.
[0176] Even more preferably, [0177] X is a divalent unit (X.sup.1), where R.sup.10 and R.sup.11 are independently hydrogen or methyl; anc [0178] Y is (C.sub.1-C.sub.4)-alkyl which is substituted by p radicals selected from the group consisting of CO.sub.2R.sup.e, CONR.sup.bR.sup.h, CONR.sup.eS(O)R.sup.a, CONR.sup.eSO.sub.2R.sup.a and CONR.sup.b1SO.sub.2NR.sup.b2R.sup.b3, where [0179] R.sup.e in CO.sub.2R.sup.e is hydrogen, (C.sub.1-C.sub.6)-alkyl which may carry a cyano substituent; (C.sub.3-C.sub.6)-cycloalkyl; (C.sub.2-C.sub.4)-alkynyl or phenyl-(C.sub.1-C.sub.3)-alkyl; preferably hydrogen, (C.sub.1-C.sub.6)-alkyl or (C.sub.3-C.sub.6)-cycloalkyl; more preferably hydrogen or (C.sub.1-C.sub.6)-alkyl (e.g. hydrogen or (C.sub.1-C.sub.4)-alkyl; specifically hydrogen or methyl), specifically (C.sub.1-C.sub.6)-alkyl (e.g. (C.sub.1-C.sub.4)-alkyl; specifically methyl); [0180] R.sup.b in CONR.sup.bR.sup.h is hydrogen or (C.sub.1-C.sub.3)-alkyl; [0181] R.sup.h in CONR.sup.bR.sup.h is (C.sub.1-C.sub.3)-alkoxy; [0182] R.sup.e in CONR.sup.eS(O)R.sup.a is hydrogen or (C.sub.1-C.sub.3)-alkyl; [0183] R.sup.a in CONR.sup.eS(O)R.sup.a is (C.sub.1-C.sub.6)-alkyl or (C.sub.1-C.sub.3)-haloalkyl; [0184] R.sup.e in CONR.sup.eSO.sub.2R.sup.a is hydrogen or (C.sub.1-C.sub.3)-alkyl; [0185] R.sup.a in CONR.sup.eSO.sub.2R.sup.a is (C.sub.1-C.sub.6)-alkyl or (C.sub.1-C.sub.3)-haloalkyl; [0186] R.sup.b1 in CONR.sup.b1SO.sub.2NR.sup.b2R.sup.b3 is hydrogen or (C.sub.1-C.sub.3)-alkyl; [0187] R.sup.b2 in CONR.sup.b1SO.sub.2NR.sup.b2R.sup.b3 is hydrogen or (C.sub.1-C.sub.3)-alkyl; [0188] R.sup.b3 in CONR.sup.b1SO.sub.2NR.sup.b2R.sup.b3 is (C.sub.1-C.sub.6)-alkyl; or [0189] R.sup.b2 and R.sup.b3, together with the nitrogen atom they are bound to, form a saturated 5- or 6-membered N-bound heterocyclic ring; and [0190] p is 1 or 2, preferably 1.
[0191] In this context, Y is preferably (C.sub.1-C.sub.4)-alkyl which is substituted by p radicals CO.sub.2R.sup.e, where R.sup.e is hydrogen or (C.sub.1-C.sub.4)-alkyl (e.g. hydrogen or methyl), in particular (C.sub.1-C.sub.4)-alkyl (e.g. methyl).
[0192] In an alternative even more preferred embodiment, [0193] X is a bond; and [0194] Y is (C.sub.1-C.sub.6)-alkyl which is substituted by p radicals selected from the group consisting of CO.sub.2R.sup.e, CONR.sup.bR.sup.h, CONR.sup.eS(O)R.sup.a, CONR.sup.eSO.sub.2R.sup.a and CONR.sup.b1SO.sub.2NR.sup.b2R.sup.b3 where [0195] R.sup.e in CO.sub.2R.sup.e is hydrogen, (C.sub.1-C.sub.6)-alkyl which may carry a cyano substituent; (C.sub.3-C.sub.6)-cycloalkyl; (C.sub.2-C.sub.4)-alkynyl or phenyl-(C.sub.1-C.sub.3)-alkyl; preferably hydrogen, (C.sub.1-C.sub.6)-alkyl or (C.sub.3-C.sub.6)-cycloalkyl; more preferably hydrogen or (C.sub.1-C.sub.6)-alkyl (e.g. hydrogen or (C.sub.1-C.sub.4)-alkyl; specifically hydrogen or methyl), specifically (C.sub.1-C.sub.6)-alkyl (e.g. (C.sub.1-C.sub.4)-alkyl; specifically methyl); [0196] R.sup.b in CONR.sup.bR.sup.h is hydrogen or (C.sub.1-C.sub.3)-alkyl; [0197] R.sup.h in CONR.sup.bR.sup.h is (C.sub.1-C.sub.3)-alkoxy; [0198] R.sup.e in CONR.sup.eS(O)R.sup.a is hydrogen or (C.sub.1-C.sub.3)-alkyl; [0199] R.sup.a in CONR.sup.eS(O)R.sup.a is (C.sub.1-C.sub.6)-alkyl or (C.sub.1-C.sub.3)-haloalkyl; [0200] R.sup.e in CONR.sup.eSO.sub.2R.sup.a is hydrogen or (C.sub.1-C.sub.3)-alkyl; [0201] R.sup.a in CONR.sup.eSO.sub.2R.sup.a is (C.sub.1-C.sub.6)-alkyl or (C.sub.1-C.sub.3)-haloalkyl; [0202] R.sup.b1 in CONR.sup.b1SO.sub.2NR.sup.b2R.sup.b3 is hydrogen or (C.sub.1-C.sub.3)-alkyl; [0203] R.sup.b2 in CONR.sup.b1SO.sub.2NR.sup.b2R.sup.b3 is hydrogen or (C.sub.1-C.sub.3)-alkyl; [0204] R.sup.b3 in CONR.sup.b1SO.sub.2NR.sup.b2R.sup.b3 is (C.sub.1-C.sub.6)-alkyl; or [0205] R.sup.b2 and R.sup.b3, together with the nitrogen atom they are bound to, form a saturated 5- or 6-membered N-bound heterocyclic ring; and [0206] p is 1 or 2, preferably 1.
[0207] In this latter alternative even more preferred embodiment, (C.sub.1-C.sub.6)-alkyl in Y is preferably a group-C(R.sup.101) (R.sup.111)C.sub.1-C.sub.4-alkyl which is substituted by p radicals selected from the group consisting of CO.sub.2R.sup.e, CONR.sup.bR.sup.h, CONR.sup.eS(O)R.sup.a, CONR.sup.eSO.sub.2R.sup.a and CONR.sup.b1SO.sub.2NR.sup.b2R.sup.b3, where R.sup.a, R.sup.b, R.sup.b1, R.sup.b2, R.sup.b3, R.sup.e and R.sup.h have one of the above general or preferred meanings and R.sup.101 and R.sup.111 are independently hydrogen or methyl, where however preferably one of R.sup.101 and R.sup.111 is hydrogen and the other is methyl.
[0208] In this context, Y is preferably a group-C(R.sup.101) (R.sup.111)C.sub.1-C.sub.4-alkyl which is substituted by p radicals CO.sub.2R.sup.e, where R.sup.e is hydrogen or (C.sub.1-C.sub.4)-alkyl, specifically hydrogen or methyl, and R.sup.101 and R.sup.111 are independently hydrogen or methyl, where however preferably one of R.sup.101 and R.sup.111 is hydrogen and the other is methyl.
[0209] Specifically, [0210] X is CH(CH.sub.3); and [0211] Y is (C.sub.1-C.sub.4)-alkyl which is substituted by p radicals selected from the group consisting of CO.sub.2R.sup.e, CONR.sup.bR.sup.h, CONR.sup.eS(O)R.sup.a, CONR.sup.eSO.sub.2R.sup.a and CONR.sup.b1SO.sub.2NR.sup.b2R.sup.b3, where [0212] R.sup.e in CO.sub.2R.sup.e is hydrogen or (C.sub.1-C.sub.6)-alkyl (preferably hydrogen or (C.sub.1-C.sub.4)-alkyl; specifically hydrogen or methyl; [0213] R.sup.b in CONR.sup.bR.sup.h is hydrogen or (C.sub.1-C.sub.3)-alkyl; [0214] R.sup.h in CONR.sup.bR.sup.h is (C.sub.1-C.sub.3)-alkoxy; [0215] R.sup.e in CONR.sup.eS(O)R.sup.a is hydrogen or (C.sub.1-C.sub.3)-alkyl; [0216] R.sup.a in CONR.sup.eS(O)R.sup.a is (C.sub.1-C.sub.6)-alkyl or (C.sub.1-C.sub.3)-haloalkyl; [0217] R.sup.e in CONR.sup.eSO.sub.2R.sup.a is hydrogen or (C.sub.1-C.sub.3)-alkyl; [0218] R.sup.a in CONR.sup.eSO.sub.2R.sup.a is (C.sub.1-C.sub.6)-alkyl or (C.sub.1-C.sub.3)-haloalkyl; [0219] R.sup.b1 in CONR.sup.b1SO.sub.2NR.sup.b2R.sup.b3 is hydrogen or (C.sub.1-C.sub.3)-alkyl; [0220] R.sup.b2 in CONR.sup.b1SO.sub.2NR.sup.b2R.sup.b3 is hydrogen or (C.sub.1-C.sub.3)-alkyl; R.sup.b3 in CONR.sup.b1SO.sub.2NR.sup.b2R.sup.b3 is (C.sub.1-C.sub.6)-alkyl; or R.sup.b2 and R.sup.b3, together with the nitrogen atom they are bound to, form a saturated 5- or 6-membered N-bound heterocyclic ring; and [0221] p is 1 or 2, preferably 1.
[0222] In this context, Y is preferably (C.sub.1-C.sub.4)-alkyl which is substituted by p radicals CO.sub.2R.sup.e, where R.sup.e is hydrogen or (C.sub.1-C.sub.4)-alkyl; specifically hydrogen or methyl.
[0223] In an alternative specific embodiment, [0224] X is a bond; and [0225] Y is CH(CH.sub.3)(C.sub.1-C.sub.4)-alkyl which is substituted by p radicals selected from the group consisting of CO.sub.2R.sup.e, CONR.sup.bR.sup.h, CONR.sup.eS(O)R.sup.a, CONR.sup.eSO.sub.2R.sup.a and CONR.sup.b1SO.sub.2NR.sup.b2R.sup.b3, where [0226] R.sup.e in CO.sub.2R.sup.e is hydrogen or (C.sub.1-C.sub.6)-alkyl; [0227] R.sup.b in CONR.sup.bR.sup.h is hydrogen or (C.sub.1-C.sub.3)-alkyl; [0228] R.sup.h in CONR.sup.bR.sup.h is (C.sub.1-C.sub.3)-alkoxy; [0229] R.sup.e in CONR.sup.eS(O)R.sup.a is hydrogen or (C.sub.1-C.sub.3)-alkyl; [0230] R.sup.a in CONR.sup.eS(O)R.sup.a is (C.sub.1-C.sub.6)-alkyl or (C.sub.1-C.sub.3)-haloalkyl; [0231] R.sup.e in CONR.sup.eSO.sub.2R.sup.a is hydrogen or (C.sub.1-C.sub.3)-alkyl; [0232] R.sup.a in CONR.sup.eSO.sub.2R.sup.a is (C.sub.1-C.sub.6)-alkyl or (C.sub.1-C.sub.3)-haloalkyl; [0233] R.sup.b1 in CONR.sup.b1SO.sub.2NR.sup.b2R.sup.b3 is hydrogen or (C.sub.1-C.sub.3)-alkyl; [0234] R.sup.b2 in CONR.sup.b1SO.sub.2NR.sup.b2R.sup.b3 is hydrogen or (C.sub.1-C.sub.3)-alkyl; [0235] R.sup.b3 in CONR.sup.b1SO.sub.2NR.sup.b2R.sup.b3 is (C.sub.1-C.sub.6)-alkyl; or [0236] R.sup.b2 and R.sup.b3, together with the nitrogen atom they are bound to, form a saturated 5- or 6-membered N-bound heterocyclic ring; and [0237] p is 1 or 2, preferably 1
[0238] In this context, Y is preferably CH(CH.sub.3)(C.sub.1-C.sub.4)-alkyl which is substituted by p radicals CO.sub.2R.sup.e, where R.sup.e is hydrogen or (C.sub.1-C.sub.4)-alkyl.
[0239] In an alternatively preferred embodiment, -X-Y form together a group of the formula (XY1) or (XY2)
##STR00011##
[0240] where [0241] # designates the attachment point to NR.sup.9; [0242] R.sup.A, R.sup.B, R.sup.C, R.sup.D, R.sup.E and R.sup.F, independently of each other, have one of the meanings given for R.sup.10 and R.sup.11; or [0243] R.sup.A and R.sup.c, together with the carbon atoms they are bound to, form a 3-, 4-, 5- or 6-membered saturated or partially unsaturated carbocyclic ring; or [0244] R.sup.c and R.sup.E, together with the carbon atoms they are bound to, form a 3-, 4-, 5- or 6-membered saturated or partially unsaturated carbocyclic ring; or [0245] R.sup.A and R.sup.E, together with the carbon atoms they are bound to, form a 3-, 4-, 5- or 6-membered saturated or partially unsaturated carbocyclic ring.
[0246] R.sup.e in groups (XY1) and (XY2) is preferably hydrogen, (C.sub.1-C.sub.6)-alkyl or (C.sub.3-C.sub.6)-cycloalkyl; more preferably hydrogen or (C.sub.1-C.sub.6)-alkyl, and is specifically (C.sub.1-C.sub.6)-alkyl.
[0247] More preferably, [0248] in group of the formula (XY1) [0249] R.sup.A is hydrogen or methyl; and [0250] R.sup.B, R.sup.c and R.sup.D are hydrogen; and
[0251] in group of the formula (XY2) [0252] R.sup.A is hydrogen or methyl; and [0253] R.sup.B, R.sup.C, R.sup.D, R.sup.E and R.sup.F are hydrogen; or [0254] R.sup.A and R.sup.E, together with the carbon atoms they are bound to, form a 5- or 6-membered saturated or partly unsaturated carbocyclic ring; and form preferably a 5-membered partly unsaturated carbocyclic ring; and [0255] R.sup.B, R.sup.C, R.sup.D and R.sup.F are hydrogen; [0256] and [0257] R.sup.e is hydrogen or (C.sub.1-C.sub.4)-alkyl.
[0258] In an alternatively preferred embodiment, -X-Y form together a group of the formula (XY1) or (XY2)
##STR00012##
[0259] where [0260] # designates the attachment point to NR.sup.9; [0261] R.sup.A and R.sup.C, together with the carbon atoms they are bound to, form a 3-, 4-, 5- or 6-membered saturated or partially unsaturated heterocyclic ring containing 1 or 2 oxygen atoms as ring members; or [0262] R.sup.c and R.sup.E, together with the carbon atoms they are bound to, form a 3-, 4-, 5- or 6-membered saturated or partially unsaturated heterocyclic ring containing 1 or 2 oxygen atoms as ring members; or [0263] R.sup.A and R.sup.E, together with the carbon atoms they are bound to, form a 3-, 4-, 5- or 6-membered saturated or partially unsaturated heterocyclic ring containing 1 or 2 oxygen atoms as ring members.
[0264] R.sup.e in this context is preferably hydrogen, (C.sub.1-C.sub.6)-alkyl or (C.sub.3-C.sub.6)-cycloalkyl; more preferably hydrogen or (C.sub.1-C.sub.6)-alkyl, and is specifically (C.sub.1-C.sub.6)-alkyl.
[0265] More preferably, [0266] R.sup.A and R.sup.E, together with the carbon atoms they are bound to, form a 5- or 6-membered saturated or partly unsaturated heterocyclic ring containing one oxygen atom as ring member; and form even more preferably a 5-membered saturated or partly unsaturated heterocyclic ring containing one oxygen atom as ring member; and [0267] R.sup.B, R.sup.C, R.sup.D and R.sup.F are hydrogen; [0268] and [0269] R.sup.e is (C.sub.1-C.sub.4)-alkyl.
[0270] In a particular embodiment, in the compounds of formula (I), the substituents have the following meanings: [0271] R.sup.1 hydrogen; [0272] R.sup.2 is hydrogen or halogen; [0273] R.sup.3 is hydrogen, halogen, (C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-haloalkyl, (C.sub.1-C.sub.3)-alkoxy or (C.sub.1-C.sub.3)-haloalkoxy; [0274] R.sup.4 is hydrogen or halogen; [0275] R.sup.5 is hydrogen, halogen, (C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-haloalkyl, (C.sub.1-C.sub.3)-alkoxy or (C.sub.1-C.sub.3)-haloalkoxy; [0276] R.sup.6 is hydrogen; [0277] R.sup.7 and R.sup.8, independently of each other, are (C.sub.1-C.sub.6)-alkyl or (C.sub.2-C.sub.6)-alkenyl; preferably (C.sub.1-C.sub.6)-alkyl; [0278] R.sup.9 hydrogen; and [0279] X is a bond; and Y is Z; where Z is a five- or six-membered saturated or partly unsaturated carbocyclic ring which is substituted by p radicals CO.sub.2R.sup.e, where R.sup.e is hydrogen, (C.sub.1-C.sub.6)-alkyl or (C.sub.3-C.sub.6)-cycloalkyl, preferably hydrogen or (C.sub.1-C.sub.6)-alkyl; or [0280] X is a bond; and Y is Z; where Z is a five- or six-membered saturated or partly unsaturated heterocyclic ring containing one oxygen atom as ring member, where the ring is substituted by p radicals CO.sub.2R.sup.e, where R.sup.e is hydrogen, (C.sub.1-C.sub.6)-alkyl or (C.sub.3-C.sub.6)-cycloalkyl, preferably hydrogen or (C.sub.1-C.sub.6)-alkyl; or [0281] X is a divalent unit (X.sup.1), where R.sup.10 and R.sup.11 are independently of each other hydrogen or (C.sub.1-C.sub.6)-alkyl; and Y is (C.sub.1-C.sub.4)-alkyl which is substituted by p radicals selected from the group consisting of CO.sub.2R.sup.e, CONR.sup.bR.sup.h, CONR.sup.eS(O)R.sup.a, CONR.sup.e- SO.sub.2R.sup.a and CONR.sup.b1SO.sub.2NR.sup.b2R.sup.b3, where [0282] R.sup.e in CO.sub.2R.sup.e is hydrogen, (C.sub.1-C.sub.6)-alkyl which may carry a cyano substituent; (C.sub.3-C.sub.6)-cycloalkyl; (C.sub.2-C.sub.4)-alkynyl or phenyl-(C.sub.1-C.sub.3)-alkyl; preferably hydrogen, (C.sub.1-C.sub.6)-alkyl or (C.sub.3-C.sub.6)-cycloalkyl; in particular hydrogen or (C.sub.1-C.sub.6)-alkyl; specifically (C.sub.1-C.sub.6)-alkyl; [0283] R.sup.b in CONR.sup.bR.sup.h is hydrogen or (C.sub.1-C.sub.3)-alkyl; [0284] R.sup.h in CONR.sup.bR.sup.h is (C.sub.1-C.sub.3)-alkoxy; [0285] R.sup.e in CONR.sup.eS(O)R.sup.a is hydrogen or (C.sub.1-C.sub.3)-alkyl; [0286] R.sup.a in CONR.sup.eS(O)R.sup.a is (C.sub.1-C.sub.6)-alkyl or (C.sub.1-C.sub.3)-haloalkyl; [0287] R.sup.e in CONR.sup.eSO.sub.2R.sup.a is hydrogen or (C.sub.1-C.sub.3)-alkyl; [0288] R.sup.a in CONR.sup.eSO.sub.2R.sup.a is (C.sub.1-C.sub.6)-alkyl or (C.sub.1-C.sub.3)-haloalkyl; [0289] R.sup.b1 in CONR.sup.b1SO.sub.2NR.sup.b2R.sup.b3 is hydrogen or (C.sub.1-C.sub.3)-alkyl; [0290] R.sup.b2 in CONR.sup.b1SO.sub.2NR.sup.b2R.sup.b3 is hydrogen or (C.sub.1-C.sub.3)-alkyl; [0291] R.sup.b3 in CONR.sup.b1SO.sub.2NR.sup.b2R.sup.b3 is (C.sub.1-C.sub.6)-alkyl; or [0292] R.sup.b2 and R.sup.b3, together with the nitrogen atom they are bound to, form a saturated 5- or 6-membered N-bound heterocyclic ring; and [0293] p is 1 or 2, preferably 1.
[0294] In a more particular embodiment, in the compounds of formula (I), the substituents have the following meanings: [0295] R.sup.1 hydrogen; [0296] R.sup.2 is hydrogen or halogen; [0297] R.sup.3 is hydrogen, halogen, (C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-haloalkyl, (C.sub.1-C.sub.3)-alkoxy or (C.sub.1-C.sub.3)-haloalkoxy; [0298] R.sup.4 is hydrogen or halogen; [0299] R.sup.5 is hydrogen, halogen, (C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-haloalkyl, (C.sub.1-C.sub.3)-alkoxy or (C.sub.1-C.sub.3)-haloalkoxy; [0300] R.sup.6 is hydrogen; [0301] R.sup.7 and R.sup.8, independently of each other, are (C.sub.1-C.sub.6)-alkyl or (C.sub.2-C.sub.6)-alkenyl; preferably (C.sub.1-C.sub.6)-alkyl; [0302] R.sup.9 hydrogen; and [0303] X is a bond; and Y is Z; where Z is a five- or six-membered saturated or partly unsaturated carbocyclic ring which is substituted by p radicals CO.sub.2R.sup.e, where R.sup.e is hydrogen, (C.sub.1-C.sub.6)-alkyl or (C.sub.3-C.sub.6)-cycloalkyl, preferably hydrogen or (C.sub.1-C.sub.6)-alkyl; or [0304] X is a divalent unit (X.sup.1), where R.sup.10 and R.sup.11 are independently of each other hydrogen or (C.sub.1-C.sub.6)-alkyl; and Y is (C.sub.1-C.sub.4)-alkyl which is substituted by p radicals selected from the group consisting of CO.sub.2R.sup.e, CONR.sup.bR.sup.h, CONR.sup.eS(O)R.sup.a, CONR.sup.e- SO.sub.2R.sup.a and CONR.sup.b1SO.sub.2NR.sup.b2R.sup.b3, where [0305] R.sup.e in CO.sub.2R.sup.e is hydrogen, (C.sub.1-C.sub.6)-alkyl which may carry a cyano substituent; (C.sub.3-C.sub.6)-cycloalkyl; (C.sub.2-C.sub.4)-alkynyl or phenyl-(C.sub.1-C.sub.3)-alkyl; preferably hydrogen, (C.sub.1-C.sub.6)-alkyl or (C.sub.3-C.sub.6)-cycloalkyl; in particular hydrogen or (C.sub.1-C.sub.6)-alkyl; specifically (C.sub.1-C.sub.6)-alkyl; [0306] R.sup.b in CONR.sup.bR.sup.h is hydrogen or (C.sub.1-C.sub.3)-alkyl; [0307] R.sup.h in CONR.sup.bR.sup.h is (C.sub.1-C.sub.3)-alkoxy; [0308] R.sup.e in CONR.sup.eS(O)R.sup.a is hydrogen or (C.sub.1-C.sub.3)-alkyl; [0309] R.sup.a in CONR.sup.eS(O)R.sup.a is (C.sub.1-C.sub.6)-alkyl or (C.sub.1-C.sub.3)-haloalkyl; [0310] R.sup.e in CONR.sup.eSO.sub.2R.sup.a is hydrogen or (C.sub.1-C.sub.3)-alkyl; [0311] R.sup.a in CONR.sup.eSO.sub.2R.sup.a is (C.sub.1-C.sub.6)-alkyl or (C.sub.1-C.sub.3)-haloalkyl; [0312] R.sup.b1 in CONR.sup.b1SO.sub.2NR.sup.b2R.sup.b3 is hydrogen or (C.sub.1-C.sub.3)-alkyl; [0313] R.sup.b2 in CONR.sup.b1SO.sub.2NR.sup.b2R.sup.b3 is hydrogen or (C.sub.1-C.sub.3)-alkyl; [0314] R.sup.b3 in CONR.sup.b1SO.sub.2NR.sup.b2R.sup.b3 is (C.sub.1-C.sub.6)-alkyl; or
[0315] R.sup.b2 and R.sup.b3, together with the nitrogen atom they are bound to, form a saturated 5- or 6-membered N-bound heterocyclic ring; and [0316] p is 1 or 2, preferably 1.
[0317] In an even more particular embodiment, in the compounds of formula (I), the substituents have the following meanings: [0318] R.sup.1 is hydrogen; [0319] R.sup.2 is hydrogen; [0320] R.sup.3 is hydrogen, halogen, (C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-haloalkyl, (C.sub.1-C.sub.3)-alkoxy or (C.sub.1-C.sub.3)-haloalkoxy; [0321] R.sup.4 is hydrogen; [0322] R.sup.5 is hydrogen or halogen; [0323] R.sup.6 is hydrogen; [0324] R.sup.7 and R.sup.8, independently of each other, are (C.sub.1-C.sub.6)-alkyl; preferably methyl or ethyl; [0325] R.sup.9 hydrogen; and [0326] X is a bond; and Y is Z; where Z is a five-membered partly unsaturated carbocyclic ring which is substituted by p radicals CO.sub.2R.sup.e, where R.sup.e is hydrogen or (C.sub.1-C.sub.6)-alkyl (preferably hydrogen or (C.sub.1-C.sub.4)-alkyl; in particular hydrogen or methyl); or [0327] X is a bond; and Y is Z; where Z is a five-membered saturated or partly unsaturated heterocyclic ring containing one oxygen atom as ring member, where the ring is substituted by p radicals CO.sub.2R.sup.e, where R.sup.e is hydrogen or (C.sub.1-C.sub.6)-alkyl; or [0328] X is a divalent unit (X.sup.1), where R.sup.10 and R.sup.11 are independently of each other hydrogen or methyl; and Y is (C.sub.1-C.sub.4)-alkyl which is substituted by p radicals CO.sub.2R.sup.e, where R.sup.e is hydrogen or (C.sub.1-C.sub.6)-alkyl (preferably hydrogen or (C.sub.1-C.sub.4)-alkyl; in particular hydrogen or methyl); and [0329] p is 1 or 2, preferably 1.
[0330] In a specific embodiment, in the compounds of formula (I), the substituents have the following meanings: [0331] R.sup.1 is hydrogen; [0332] R.sup.2 is hydrogen; [0333] R.sup.3 is hydrogen, halogen, (C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-haloalkyl, (C.sub.1-C.sub.3)-alkoxy or (C.sub.1-C.sub.3)-haloalkoxy; [0334] R.sup.4 is hydrogen; [0335] R.sup.5 is hydrogen or halogen; [0336] R.sup.6 is hydrogen; [0337] R.sup.7 and R.sup.8, independently of each other, are (C.sub.1-C.sub.4)-alkyl, preferably methyl or ethyl, in particular methyl; [0338] R.sup.9 hydrogen; and [0339] X is a bond; and Y is Z; where Z is a five-membered partly unsaturated carbocyclic ring which is substituted by p radicals CO.sub.2R.sup.e, where R.sup.e is hydrogen or (C.sub.1-C.sub.6)-alkyl (preferably hydrogen or (C.sub.1-C.sub.4)-alkyl; in particular hydrogen or methyl); or [0340] X is a divalent unit (X.sup.1), where R.sup.10 and R.sup.11 are independently of each other hydrogen or methyl; and Y is (C.sub.1-C.sub.4)-alkyl which is substituted by p radicals CO.sub.2R.sup.e, where R.sup.e is hydrogen or (C.sub.1-C.sub.6)-alkyl (preferably hydrogen or (C.sub.1-C.sub.4)-alkyl; in particular hydrogen or methyl); and [0341] p is 1 or 2, preferably 1.
[0342] In a more specific embodiment, in the compounds of formula (I), the substituents have the following meanings: [0343] R.sup.1 hydrogen; [0344] R.sup.2 is hydrogen; [0345] R.sup.3 is halogen, (C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-haloalkyl, (C.sub.1-C.sub.3)-alkoxy or (C.sub.1-C.sub.3)-haloalkoxy; [0346] R.sup.4 is hydrogen; [0347] R.sup.5 is hydrogen or halogen; [0348] R.sup.6 is hydrogen; [0349] R.sup.7 and R.sup.8, independently of each other, are (C.sub.1-C.sub.4)-alkyl, preferably methyl or ethyl, in particular methyl; [0350] R.sup.9 hydrogen; and [0351] X is a bond; and Y is Z; where Z is a five-membered partly unsaturated carbocyclic ring which is substituted by p radicals CO.sub.2R.sup.e, where R.sup.e is hydrogen or (C.sub.1-C.sub.6)-alkyl (preferably hydrogen or (C.sub.1-C.sub.4)-alkyl; in particular hydrogen or methyl); or [0352] X is a divalent unit (X.sup.1), where one of R.sup.10 and R.sup.11 is hydrogen and the other is methyl; and Y is (C.sub.1-C.sub.4)-alkyl which is substituted by p radicals CO.sub.2R.sup.e, where R.sup.e is hydrogen or (C.sub.1-C.sub.6)-alkyl (preferably hydrogen or (C.sub.1-C.sub.4)-alkyl; in particular hydrogen or methyl); and [0353] p is 1.
[0354] In a very specific embodiment, in the compounds of formula (I), the substituents have the following meanings: [0355] R.sup.1 hydrogen; [0356] R.sup.2 is hydrogen; [0357] R.sup.3 is halogen, (C.sub.1-C.sub.3)-alkyl or (C.sub.1-C.sub.3)-haloalkoxy; [0358] R.sup.4 is hydrogen; [0359] R.sup.5 is hydrogen or halogen; [0360] R.sup.6 is hydrogen; [0361] R.sup.7 and R.sup.8 are methyl; [0362] R.sup.9 hydrogen; and [0363] X is a bond; and Y is Z; where Z is a five-membered partly unsaturated carbocyclic ring which is substituted by p radicals CO.sub.2R.sup.e, where R.sup.e is hydrogen or (C.sub.1-C.sub.4)-alkyl (in particular hydrogen or methyl); or [0364] X is a divalent unit (X.sup.1), where one of R.sup.10 and R.sup.11 is hydrogen and the other is methyl; and Y is (C.sub.1-C.sub.4)-alkyl which is substituted by p radicals CO.sub.2R.sup.e, where R.sup.e is (C.sub.1-C.sub.4)-alkyl (in particular hydrogen or methyl); and [0365] p is 1.
[0366] In an alternative particular embodiment, in the compounds of formula (I), the substituents have the following meanings: [0367] R.sup.1 hydrogen; [0368] R.sup.2 is hydrogen or halogen; [0369] R.sup.3 is hydrogen, halogen, (C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-haloalkyl, (C.sub.1-C.sub.3)-alkoxy or (C.sub.1-C.sub.3)-haloalkoxy; [0370] R.sup.4 is hydrogen or halogen; [0371] R.sup.5 is hydrogen, halogen, (C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-haloalkyl, (C.sub.1-C.sub.3)-alkoxy or (C.sub.1-C.sub.3)-haloalkoxy; [0372] R.sup.6 is hydrogen; [0373] R.sup.7 and R.sup.8, independently of each other, are (C.sub.1-C.sub.6)-alkyl or (C.sub.2-C.sub.6)-alkenyl; preferably (C.sub.1-C.sub.6)-alkyl; [0374] R.sup.9 hydrogen; and [0375] X is a bond; and Y is Z; where Z is a five- or six-membered saturated or partly unsaturated carbocyclic ring which is substituted by p radicals CO.sub.2R.sup.e, where R.sup.e is hydrogen, (C.sub.1-C.sub.6)-alkyl or (C.sub.3-C.sub.6)-cycloalkyl, preferably hydrogen or (C.sub.1-C.sub.6)-alkyl (more preferably hydrogen or (C.sub.1-C.sub.4)-alkyl; in particular hydrogen or methyl); or Z is a five- or six-membered saturated or partly unsaturated heterocyclic ring containing one oxygen atom as ring member, where the ring is substituted by p radicals CO.sub.2R.sup.e, where R.sup.e is hydrogen, (C.sub.1-C.sub.6)-alkyl or (C.sub.3-C.sub.6)-cycloalkyl, preferably hydrogen or (C.sub.1-C.sub.6)-alkyl; or [0376] Y is (C.sub.1-C.sub.6)-alkyl which is substituted by p radicals selected from the group consisting of CO.sub.2R.sup.e, CONR.sup.bR.sup.h, CONR.sup.eS(O)R.sup.a, CONR.sup.eSO.sub.2R.sup.a and CONR.sup.b1SO.sub.2NR.sup.b2R.sup.b3, where [0377] R.sup.e in CO.sub.2R.sup.e is hydrogen, (C.sub.1-C.sub.6)-alkyl which may carry a cyano substituent; (C.sub.3-C.sub.6)-cycloalkyl; (C.sub.2-C.sub.4)-alkynyl or phenyl-(C.sub.1-C.sub.3)-alkyl; preferably hydrogen, (C.sub.1-C.sub.6)-alkyl or (C.sub.3-C.sub.6)-cycloalkyl; in particular hydrogen or (C.sub.1-C.sub.6)-alkyl (more particularly hydrogen or (C.sub.1-C.sub.4)-alkyl; e.g. hydrogen or methyl); specifically (C.sub.1-C.sub.6)-alkyl; R.sup.b in CONR.sup.bR.sup.h is hydrogen or (C.sub.1-C.sub.3)-alkyl; [0378] R.sup.h in CONR.sup.bR.sup.h is (C.sub.1-C.sub.3)-alkoxy; [0379] R.sup.e in CONR.sup.eS(O)R.sup.a is hydrogen or (C.sub.1-C.sub.3)-alkyl; [0380] R.sup.a in CONR.sup.eS(O)R.sup.a is (C.sub.1-C.sub.6)-alkyl or (C.sub.1-C.sub.3)-haloalkyl; [0381] R.sup.e in CONR.sup.eSO.sub.2R.sup.a is hydrogen or (C.sub.1-C.sub.3)-alkyl; [0382] R.sup.a in CONR.sup.eSO.sub.2R.sup.a is (C.sub.1-C.sub.6)-alkyl or (C.sub.1-C.sub.3)-haloalkyl; [0383] R.sup.b1 in CONR.sup.b1SO.sub.2NR.sup.b2R.sup.b3 is hydrogen or (C.sub.1-C.sub.3)-alkyl; [0384] R.sup.b2 in CONR.sup.b1SO.sub.2NR.sup.b2R.sup.b3 is hydrogen or (C.sub.1-C.sub.3)-alkyl; [0385] R.sup.b3 in CONR.sup.b1SO.sub.2NR.sup.b2R.sup.b3 is (C.sub.1-C.sub.6)-alkyl; or [0386] R.sup.b2 and R.sup.b3, together with the nitrogen atom they are bound to, form a saturated 5- or 6-membered N-bound heterocyclic ring; and [0387] p is 1 or 2, preferably 1.
[0388] In an alternative more particular embodiment, in the compounds of formula (I), the substituents have the following meanings: [0389] R.sup.1 hydrogen; [0390] R.sup.2 is hydrogen or halogen; [0391] R.sup.3 is hydrogen, halogen, (C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-haloalkyl, (C.sub.1-C.sub.3)-alkoxy or (C.sub.1-C.sub.3)-haloalkoxy; [0392] R.sup.4 is hydrogen or halogen; [0393] R.sup.5 is hydrogen, halogen, (C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-haloalkyl, (C.sub.1-C.sub.3)-alkoxy or (C.sub.1-C.sub.3)-haloalkoxy; [0394] R.sup.6 is hydrogen; [0395] R.sup.7 and R.sup.8, independently of each other, are (C.sub.1-C.sub.6)-alkyl or (C.sub.2-C.sub.6)-alkenyl; preferably (C.sub.1-C.sub.6)-alkyl; [0396] R.sup.9 hydrogen; and [0397] X is a bond; and Y is Z; where Z is a five- or six-membered saturated or partly unsaturated carbocyclic ring which is substituted by p radicals CO.sub.2R.sup.e, where R.sup.e is hydrogen, (C.sub.1-C.sub.6)-alkyl or (C.sub.3-C.sub.6)-cycloalkyl, preferably hydrogen or (C.sub.1-C.sub.6)-alkyl (preferably hydrogen or (C.sub.1-C.sub.4)-alkyl; in particular hydrogen or methyl); or Y is (C.sub.1-C.sub.6)-alkyl which is substituted by p radicals selected from the group consisting of CO.sub.2R.sup.e, CONR.sup.bR.sup.h, CONR.sup.eS(O)R.sup.a, CONR.sup.eSO.sub.2R.sup.a and CONR.sup.b1SO.sub.2NR.sup.b2R.sup.b3, where [0398] R.sup.e in CO.sub.2R.sup.e is hydrogen, (C.sub.1-C.sub.6)-alkyl which may carry a cyano substituent; (C.sub.3-C.sub.6)-cycloalkyl; (C.sub.2-C.sub.4)-alkynyl or phenyl-(C.sub.1-C.sub.3)-alkyl; preferably hydrogen, (C.sub.1-C.sub.6)-alkyl or (C.sub.3-C.sub.6)-cycloalkyl; in particular hydrogen or (C.sub.1-C.sub.6)-alkyl (more particularly hydrogen or (C.sub.1-C.sub.4)-alkyl; e.g. hydrogen or methyl); specifically (C.sub.1-C.sub.6)-alkyl; [0399] R.sup.b in CONR.sup.bR.sup.h is hydrogen or (C.sub.1-C.sub.3)-alkyl; [0400] R.sup.h in CONR.sup.bR.sup.h is (C.sub.1-C.sub.3)-alkoxy; [0401] R.sup.e in CONR.sup.eS(O)R.sup.a is hydrogen or (C.sub.1-C.sub.3)-alkyl; [0402] R.sup.a in CONR.sup.eS(O)R.sup.a is (C.sub.1-C.sub.6)-alkyl or (C.sub.1-C.sub.3)-haloalkyl; [0403] R.sup.e in CONR.sup.eSO.sub.2R.sup.a is hydrogen or (C.sub.1-C.sub.3)-alkyl; [0404] R.sup.a in CONR.sup.eSO.sub.2R.sup.a is (C.sub.1-C.sub.6)-alkyl or (C.sub.1-C.sub.3)-haloalkyl; [0405] R.sup.b1 in CONR.sup.b1SO.sub.2NR.sup.b2R.sup.b3 is hydrogen or (C.sub.1-C.sub.3)-alkyl; [0406] R.sup.b2 in CONR.sup.b1SO.sub.2NR.sup.b2R.sup.b3 is hydrogen or (C.sub.1-C.sub.3)-alkyl; [0407] R.sup.b3 in CONR.sup.b1SO.sub.2NR.sup.b2R.sup.b3 is (C.sub.1-C.sub.6)-alkyl; or [0408] R.sup.b2 and R.sup.b3, together with the nitrogen atom they are bound to, form a saturated 5- or 6-membered N-bound heterocyclic ring; and [0409] p is 1 or 2, preferably 1.
[0410] In an even more particular embodiment, in the compounds of formula (I), the substituents have the following meanings: [0411] R.sup.1 is hydrogen; [0412] R.sup.2 is hydrogen; [0413] R.sup.3 is hydrogen, halogen, (C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-haloalkyl, (C.sub.1-C.sub.3)-alkoxy or (C.sub.1-C.sub.3)-haloalkoxy; [0414] R.sup.4 is hydrogen; [0415] R.sup.5 is hydrogen or halogen; [0416] R.sup.6 is hydrogen; [0417] R.sup.7 and R.sup.8, independently of each other, are (C.sub.1-C.sub.6)-alkyl; preferably methyl or ethyl; [0418] R.sup.9 hydrogen; and [0419] X is a bond; and Y is Z; where Z is a five-membered partly unsaturated carbocyclic ring which is substituted by p radicals CO.sub.2R.sup.e, where R.sup.e is hydrogen or (C.sub.1-C.sub.6)-alkyl (preferably hydrogen or (C.sub.1-C.sub.4)-alkyl; in particular hydrogen or methyl); or Z is a five-membered saturated or partly unsaturated heterocyclic ring containing one oxygen atom as ring member, where the ring is substituted by p radicals CO.sub.2R.sup.e, where R.sup.e is hydrogen or (C.sub.1-C.sub.6)-alkyl; or [0420] Y is (C.sub.1-C.sub.6)-alkyl which is substituted by p radicals CO.sub.2R.sup.e, where R.sup.e is hydrogen or (C.sub.1-C.sub.6)-alkyl (preferably hydrogen or (C.sub.1-C.sub.4)-alkyl; in particular hydrogen or methyl); and [0421] p is 1 or 2, preferably 1.
[0422] In a specific embodiment, in the compounds of formula (I), the substituents have the following meanings: [0423] R.sup.1 is hydrogen; [0424] R.sup.2 is hydrogen; [0425] R.sup.3 is hydrogen, halogen, (C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-haloalkyl, (C.sub.1-C.sub.3)-alkoxy or (C.sub.1-C.sub.3)-haloalkoxy; [0426] R.sup.4 is hydrogen; [0427] R.sup.5 is hydrogen or halogen; [0428] R.sup.6 is hydrogen; [0429] R.sup.7 and R.sup.8, independently of each other, are methyl or ethyl; [0430] R.sup.9 hydrogen; and [0431] X is a bond; and Y is Z; where Z is a five-membered partly unsaturated carbocyclic ring which is substituted by p radicals CO.sub.2R.sup.e, where R.sup.e is hydrogen or (C.sub.1-C.sub.6)-alkyl (preferably hydrogen or (C.sub.1-C.sub.4)-alkyl; in particular hydrogen or methyl); or Y is (C.sub.1-C.sub.6)-alkyl which is substituted by p radicals CO.sub.2R.sup.e, where R.sup.e is hydrogen or (C.sub.1-C.sub.6)-alkyl (preferably hydrogen or (C.sub.1-C.sub.4)-alkyl; in particular hydrogen or methyl); and [0432] p is 1 or 2, preferably 1.
[0433] In an alternative more specific embodiment, in the compounds of formula (I), the substituents have the following meanings: [0434] R.sup.1 hydrogen; [0435] R.sup.2 is hydrogen; [0436] R.sup.3 is halogen, (C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-haloalkyl, (C.sub.1-C.sub.3)-alkoxy or (C.sub.1-C.sub.3)-haloalkoxy; [0437] R.sup.4 is hydrogen; [0438] R.sup.5 is hydrogen or halogen; [0439] R.sup.6 is hydrogen; [0440] R.sup.7 and R.sup.8, independently of each other, are (C.sub.1-C.sub.4)-alkyl, preferably methyl or ethyl, in particular methyl; [0441] R.sup.9 hydrogen; and [0442] X is a bond; and Y is Z; where Z is a five-membered partly unsaturated carbocyclic ring which is substituted by p radicals CO.sub.2R.sup.e, where R.sup.e is hydrogen or (C.sub.1-C.sub.6)-alkyl (preferably hydrogen or (C.sub.1-C.sub.4)-alkyl; in particular hydrogen or methyl); or Y is (C.sub.1-C.sub.6)-alkyl which is substituted by p radicals CO.sub.2R.sup.e, where R.sup.e is hydrogen or (C.sub.1-C.sub.6)-alkyl (preferably hydrogen or (C.sub.1-C.sub.4)-alkyl; in particular hydrogen or methyl); and [0443] p is 1.
[0444] In a very specific embodiment, in the compounds of formula (I), the substituents have the following meanings: [0445] R.sup.1 hydrogen; [0446] R.sup.2 is hydrogen; [0447] R.sup.3 is halogen, (C.sub.1-C.sub.3)-alkyl or (C.sub.1-C.sub.3)-haloalkoxy; [0448] R.sup.4 is hydrogen; [0449] R.sup.5 is hydrogen or halogen; [0450] R.sup.6 is hydrogen; [0451] R.sup.7 and R.sup.8 are methyl; [0452] R.sup.9 hydrogen; and [0453] X is a bond; and Y is Z; where Z is a five-membered partly unsaturated carbocyclic ring which is substituted by p radicals CO.sub.2R.sup.e, where R.sup.e is hydrogen or (C.sub.1-C.sub.4)-alkyl (in particular hydrogen or methyl); or [0454] Y is (C.sub.1-C.sub.6)-alkyl which is substituted by p radicals CO.sub.2R.sup.e, where R.sup.e is (C.sub.1-C.sub.4)-alkyl (in particular hydrogen or methyl); and [0455] p is 1.
[0456] In the above particular and specific embodiments, the five-membered partly unsaturated carbocyclic ring Z is preferably a ring Z.sup.9 (depicted below), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is CO.sub.2R.sup.e.
[0457] In another particular embodiment, in the compounds of formula (I), the substituents have the following meanings: [0458] R.sup.1 hydrogen; [0459] R.sup.2 is hydrogen or halogen; [0460] R.sup.3 is hydrogen, halogen, (C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-haloalkyl, (C.sub.1-C.sub.3)-alkoxy or (C.sub.1-C.sub.3)-haloalkoxy; [0461] R.sup.4 is hydrogen or halogen; [0462] R.sup.5 is hydrogen, halogen, (C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-haloalkyl, (C.sub.1-C.sub.3)-alkoxy or (C.sub.1-C.sub.3)-haloalkoxy; [0463] R.sup.6 is hydrogen; [0464] R.sup.7 and R.sup.8, independently of each other, are (C.sub.1-C.sub.6)-alkyl or (C.sub.2-C.sub.6)-alkenyl; preferably (C.sub.1-C.sub.6)-alkyl; [0465] R.sup.9 hydrogen; and [0466] -X-Y form together a group of the formula (XY1) or (XY2)
##STR00013##
[0467] where [0468] # designates the attachment point to NR.sup.9; [0469] R.sup.A, R.sup.B, R.sup.C, R.sup.D, R.sup.E and R.sup.F, independently of each other, have one of the meanings given for R.sup.10 and R.sup.11; or [0470] R.sup.A and R.sup.c, together with the carbon atoms they are bound to, form a 3-, 4-, 5- or 6-membered saturated or partially unsaturated carbocyclic ring; or [0471] R.sup.c and R.sup.E, together with the carbon atoms they are bound to, form a 3-, 4-, 5- or 6-membered saturated or partially unsaturated carbocyclic ring; or [0472] R.sup.A and R.sup.E, together with the carbon atoms they are bound to, form a 3-, 4-, 5- or 6-membered saturated or partially unsaturated carbocyclic ring. [0473] R.sup.e in groups (XY1) and (XY2) is preferably hydrogen, (C.sub.1-C.sub.6)-alkyl or (C.sub.3-C.sub.6)-cycloalkyl; more preferably hydrogen or (C.sub.1-C.sub.6)-alkyl, and is specifically (C.sub.1-C.sub.6)-alkyl.
[0474] In another more particular embodiment, in the compounds of formula (I), the substituents have the following meanings: [0475] R.sup.1 is hydrogen; [0476] R.sup.2 is hydrogen; [0477] R.sup.3 is hydrogen, halogen, (C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-haloalkyl, (C.sub.1-C.sub.3)-alkoxy or (C.sub.1-C.sub.3)-haloalkoxy; [0478] R.sup.4 is hydrogen; [0479] R.sup.5 is hydrogen or halogen; [0480] R.sup.6 is hydrogen; [0481] R.sup.7 and R.sup.8, independently of each other, are (C.sub.1-C.sub.6)-alkyl; preferably methyl or ethyl, in particular methyl; [0482] R.sup.9 hydrogen; and [0483] X-Y form together a group of the formula (XY1) or (XY2), where in group of the formula (XY1) [0484] R.sup.A is hydrogen or methyl; and [0485] R.sup.B, R.sup.c and R.sup.D are hydrogen; and
[0486] in group of the formula (XY2) [0487] R.sup.A is hydrogen or methyl; and [0488] R.sup.B, R.sup.C, R.sup.D, R.sup.E and R.sup.F are hydrogen; or [0489] R.sup.A and R.sup.E, together with the carbon atoms they are bound to, form a 5- or 6-membered saturated or partly unsaturated carbocyclic ring; and form preferably a 5-membered partly unsaturated carbocyclic ring; and [0490] R.sup.B, R.sup.C, R.sup.D and R.sup.F are hydrogen; [0491] and [0492] R.sup.e is hydrogen or (C.sub.1-C.sub.4)-alkyl (in particular hydrogen or methyl).
[0493] In another specific embodiment, in the compounds of formula (I), the substituents have the following meanings: [0494] R.sup.1 is hydrogen; [0495] R.sup.2 is hydrogen; [0496] R.sup.3 is halogen, (C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-haloalkyl, (C.sub.1-C.sub.3)-alkoxy or (C.sub.1-C.sub.3)-haloalkoxy; [0497] R.sup.4 is hydrogen; [0498] R.sup.5 is hydrogen or halogen; [0499] R.sup.6 is hydrogen; [0500] R.sup.7 and R.sup.8, independently of each other, are (C.sub.1-C.sub.4)-alkyl; preferably methyl or ethyl, in particular methyl; [0501] R.sup.9 hydrogen; and [0502] X-Y form together a group of the formula (XY1) or (XY2), where
[0503] in group of the formula (XY1) [0504] R.sup.A is hydrogen or methyl; and [0505] R.sup.B, R.sup.C and R.sup.D are hydrogen; and
[0506] in group of the formula (XY2) [0507] R.sup.A is hydrogen or methyl; and [0508] R.sup.B, R.sup.C, R.sup.D, R.sup.E and R.sup.F are hydrogen; or [0509] R.sup.A and R.sup.E, together with the carbon atoms they are bound to, form a 5-membered partly unsaturated carbocyclic ring; and [0510] R.sup.B, R.sup.C, R.sup.D and R.sup.F are hydrogen; [0511] and [0512] R.sup.e is hydrogen or (C.sub.1-C.sub.4)-alkyl (in particular hydrogen or methyl).
[0513] In another more specific embodiment, in the compounds of formula (I), the substituents have the following meanings: [0514] R.sup.1 is hydrogen; [0515] R.sup.2 is hydrogen; [0516] R.sup.3 is halogen, (C.sub.1-C.sub.3)-alkyl or (C.sub.1-C.sub.3)-haloalkoxy; [0517] R.sup.4 is hydrogen; [0518] R.sup.5 is hydrogen or halogen; [0519] R.sup.6 is hydrogen; [0520] R.sup.7 and R.sup.8 are methyl; [0521] R.sup.9 hydrogen; and [0522] X-Y form together a group of the formula (XY1) or (XY2), where
[0523] in group of the formula (XY1) [0524] R.sup.A is hydrogen or methyl; and [0525] R.sup.B, R.sup.C and R.sup.D are hydrogen; and
[0526] in group of the formula (XY2) [0527] R.sup.A is hydrogen or methyl; and [0528] R.sup.B, R.sup.C, R.sup.D, R.sup.E and R.sup.F are hydrogen; or [0529] R.sup.A and R.sup.E, together with the carbon atoms they are bound to, form a 5-membered partly unsaturated carbocyclic ring; and [0530] R.sup.B, R.sup.C, R.sup.D and R.sup.F are hydrogen; [0531] and [0532] R.sup.e is hydrogen or (C.sub.1-C.sub.4)-alkyl (in particular hydrogen or methyl).
[0533] In yet another particular embodiment, in the compounds of formula (I), the substituents have the following meanings: [0534] R.sup.1 hydrogen; [0535] R.sup.2 is hydrogen or halogen; [0536] R.sup.3 is hydrogen, halogen, (C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-haloalkyl, (C.sub.1-C.sub.3)-alkoxy or (C.sub.1-C.sub.3)-haloalkoxy; [0537] R.sup.4 is hydrogen or halogen; [0538] R.sup.5 is hydrogen, halogen, (C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-haloalkyl, (C.sub.1-C.sub.3)-alkoxy or (C.sub.1-C.sub.3)-haloalkoxy; [0539] R.sup.6 is hydrogen; [0540] R.sup.7 and R.sup.8, independently of each other, are (C.sub.1-C.sub.6)-alkyl or (C.sub.2-C.sub.6)-alkenyl; preferably (C.sub.1-C.sub.6)-alkyl; [0541] R.sup.9 hydrogen; and [0542] -X-Y form together a group of the formula (XY1) or (XY2)
##STR00014##
[0543] where [0544] # designates the attachment point to NR.sup.9; [0545] R.sup.A and R.sup.c, together with the carbon atoms they are bound to, form a 3-, 4-, 5- or 6-membered saturated or partially unsaturated heterocyclic ring containing 1 or 2 oxygen atoms as ring members; or [0546] R.sup.c and R.sup.E, together with the carbon atoms they are bound to, form a 3-, 4-, 5- or 6-membered saturated or partially unsaturated heterocyclic ring containing 1 or 2 oxygen atoms as ring members; or [0547] R.sup.A and R.sup.E, together with the carbon atoms they are bound to, form a 3-, 4-, 5- or 6-membered saturated or partially unsaturated heterocyclic ring containing 1 or 2 oxygen atoms as ring members. [0548] R.sup.e in this context is preferably hydrogen, (C.sub.1-C.sub.6)-alkyl or (C.sub.3-C.sub.6)-cycloalkyl; more preferably hydrogen or (C.sub.1-C.sub.6)-alkyl, and is specifically (C.sub.1-C.sub.6)-alkyl.
[0549] In yet another more particular embodiment, in the compounds of formula (I), the substituents have the following meanings: [0550] R.sup.1 is hydrogen; [0551] R.sup.2 is hydrogen; [0552] R.sup.3 is hydrogen, halogen, (C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-haloalkyl, (C.sub.1-C.sub.3)-alkoxy or (C.sub.1-C.sub.3)-haloalkoxy; [0553] R.sup.4 is hydrogen; [0554] R.sup.5 is hydrogen or halogen; [0555] R.sup.6 is hydrogen; [0556] R.sup.7 and R.sup.8, independently of each other, are (C.sub.1-C.sub.6)-alkyl; preferably methyl or ethyl; [0557] R.sup.9 hydrogen; and [0558] X-Y form together a group of the formula (XY1) or (XY2), where [0559] R.sup.A and R.sup.E, together with the carbon atoms they are bound to, form a 5- or 6-membered saturated or partly unsaturated heterocyclic ring containing one oxygen atom as ring member; and form preferably a 5-membered saturated or partly unsaturated heterocyclic ring containing one oxygen atom as ring member; [0560] R.sup.B, R.sup.C, R.sup.D and R.sup.F are hydrogen; [0561] and [0562] R.sup.e is (C.sub.1-C.sub.4)-alkyl.
[0563] Compounds (I), wherein R.sup.1, R.sup.6 and R.sup.9 are hydrogen and R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have the meanings as defined in each line of table A below are particularly preferred.
TABLE-US-00001 TABLE A No. R.sup.2 R.sup.3 R.sup.4 R.sup.5 R.sup.7 R.sup.8 1. H H H H CH.sub.3 CH.sub.3 2. H F H H CH.sub.3 CH.sub.3 3. H Cl H H CH.sub.3 CH.sub.3 4. H Br H H CH.sub.3 CH.sub.3 5. H I H H CH.sub.3 CH.sub.3 6. H CH.sub.3 H H CH.sub.3 CH.sub.3 7. H Et H H CH.sub.3 CH.sub.3 8. H CF.sub.3 H H CH.sub.3 CH.sub.3 9. H OCH.sub.3 H H CH.sub.3 CH.sub.3 10. H OCF.sub.3 H H CH.sub.3 CH.sub.3 11. H CN H H CH.sub.3 CH.sub.3 12. H H H H CH.sub.3 Et 13. H F H H CH.sub.3 Et 14. H Cl H H CH.sub.3 Et 15. H Br H H CH.sub.3 Et 16. H I H H CH.sub.3 Et 17. H CH.sub.3 H H CH.sub.3 Et 18. H Et H H CH.sub.3 Et 19. H CF.sub.3 H H CH.sub.3 Et 20. H OCH.sub.3 H H CH.sub.3 Et 21. H OCF.sub.3 H H CH.sub.3 Et 22. H CN H H CH.sub.3 Et 23. H H H H Et Et 24. H F H H Et Et 25. H Cl H H Et Et 26. H Br H H Et Et 27. H I H H Et Et 28. H CH.sub.3 H H Et Et 29. H Et H H Et Et 30. H CF.sub.3 H H Et Et 31. H OCH.sub.3 H H Et Et 32. H OCF.sub.3 H H Et Et 33. H CN H H Et Et 34. H H H H CH.sub.3 Vin 35. H F H H CH.sub.3 Vin 36. H Cl H H CH.sub.3 Vin 37. H Br H H CH.sub.3 Vin 38. H I H H CH.sub.3 Vin 39. H CH.sub.3 H H CH.sub.3 Vin 40. H Et H H CH.sub.3 Vin 41. H CF.sub.3 H H CH.sub.3 Vin 42. H OCH.sub.3 H H CH.sub.3 Vin 43. H OCF.sub.3 H H CH.sub.3 Vin 44. H CN H H CH.sub.3 Vin 45. H H H H Et Vin 46. H F H H Et Vin 47. H Cl H H Et Vin 48. H Br H H Et Vin 49. H I H H Et Vin 50. H CH.sub.3 H H Et Vin 51. H Et H H Et Vin 52. H CF.sub.3 H H Et Vin 53. H OCH.sub.3 H H Et Vin 54. H OCF.sub.3 H H Et Vin 55. H CN H H Et Vin 56. H F H F CH.sub.3 CH.sub.3 57. H Cl H F CH.sub.3 CH.sub.3 58. H Br H F CH.sub.3 CH.sub.3 59. H I H F CH.sub.3 CH.sub.3 60. H CH.sub.3 H F CH.sub.3 CH.sub.3 61. H Et H F CH.sub.3 CH.sub.3 62. H CF.sub.3 H F CH.sub.3 CH.sub.3 63. H OCH.sub.3 H F CH.sub.3 CH.sub.3 64. H OCF.sub.3 H F CH.sub.3 CH.sub.3 65. H CN H F CH.sub.3 CH.sub.3 66. H F H F CH.sub.3 Et 67. H Cl H F CH.sub.3 Et 68. H Br H F CH.sub.3 Et 69. H I H F CH.sub.3 Et 70. H CH H F CH.sub.3 Et 71. H Et H F CH.sub.3 Et 72. H CF.sub.3 H F CH.sub.3 Et 73. H OCH.sub.3 H F CH.sub.3 Et 74. H OCF.sub.3 H F CH.sub.3 Et 75. H CN H F CH.sub.3 Et 76. H F H F Et Et 77. H Cl H F Et Et 78. H Br H F Et Et 79. H I H F Et Et 80. H CH.sub.3 H F Et Et 81. H Et H F Et Et 82. H CF.sub.3 H F Et Et 83. H OCH.sub.3 H F Et Et 84. H OCF.sub.3 H F Et Et 85. H CN H F Et Et 86. H F H F CH.sub.3 Vin 87. H Cl H F CH.sub.3 Vin 88. H Br H F CH.sub.3 Vin 89. H I H F CH.sub.3 Vin 90. H CH.sub.3 H F CH.sub.3 Vin 91. H Et H F CH.sub.3 Vin 92. H CF.sub.3 H F CH.sub.3 Vin 93. H OCH.sub.3 H F CH.sub.3 Vin 94. H OCF.sub.3 H F CH.sub.3 Vin 95. H CN H F CH.sub.3 Vin 96. H F H F Et Vin 97. H Cl H F Et Vin 98. H Br H F Et Vin 99. H I H F Et Vin 100. H CH.sub.3 H F Et Vin 101. H Et H F Et Vin 102. H CF.sub.3 H F Et Vin 103. H OCH.sub.3 H F Et Vin 104. H OCF.sub.3 H F Et Vin 105. H CN H F Et Vin 106. H Cl H Cl CH.sub.3 CH.sub.3 107. H Br H Cl CH.sub.3 CH.sub.3 108. H I H Cl CH.sub.3 CH.sub.3 109. H CH.sub.3 H Cl CH.sub.3 CH.sub.3 110. H Et H Cl CH.sub.3 CH.sub.3 111. H CF.sub.3 H Cl CH.sub.3 CH.sub.3 112. H OCH.sub.3 H Cl CH.sub.3 CH.sub.3 113. H OCF.sub.3 H Cl CH.sub.3 CH.sub.3 114. H CN H Cl CH.sub.3 CH.sub.3 115. H Cl H Cl CH.sub.3 Et 116. H Br H Cl CH.sub.3 Et 117. H I H Cl CH.sub.3 Et 118. H CH.sub.3 H Cl CH.sub.3 Et 119. H Et H Cl CH.sub.3 Et 120. H CF.sub.3 H Cl CH.sub.3 Et 121. H OCH.sub.3 H Cl CH.sub.3 Et 122. H OCF.sub.3 H Cl CH.sub.3 Et 123. H CN H Cl CH.sub.3 Et 124. H Cl H Cl Et Et 125. H Br H Cl Et Et 126. H I H Cl Et Et 127. H CH.sub.3 H Cl Et Et 128. H Et H Cl Et Et 129. H CF.sub.3 H Cl Et Et 130. H OCH.sub.3 H Cl Et Et 131. H OCF.sub.3 H Cl Et Et 132. H CN H Cl Et Et 133. H Cl H Cl CH.sub.3 Vin 134. H Br H Cl CH.sub.3 Vin 135. H I H Cl CH.sub.3 Vin 136. H CH.sub.3 H Cl CH.sub.3 Vin 137. H Et H Cl CH.sub.3 Vin 138. H CF.sub.3 H Cl CH.sub.3 Vin 139. H OCH.sub.3 H Cl CH.sub.3 Vin 140. H OCF.sub.3 H Cl CH.sub.3 Vin 141. H CN H Cl CH.sub.3 Vin 142. H Cl H Cl Et Vin 143. H Br H Cl Et Vin 144. H I H Cl Et Vin 145. H CH.sub.3 H Cl Et Vin 146. H Et H Cl Et Vin 147. H CF.sub.3 H Cl Et Vin 148. H OCH.sub.3 H Cl Et Vin 149. H OCF.sub.3 H Cl Et Vin 150. H CN H Cl Et Vin 151. H Br H Br CH.sub.3 CH.sub.3 152. H Br H Br CH.sub.3 Et 153. H Br H Br Et Et 154. H Br H Br CH.sub.3 Vin 155. H Br H Br Et Vin 156. H I H I CH.sub.3 CH.sub.3 157. H I H I CH.sub.3 Et 158. H I H I Et Et 159. H I H I CH.sub.3 Vin 160. H I H I Et Vin 161. H Br H CN CH.sub.3 CH.sub.3 162. H I H CN CH.sub.3 CH.sub.3 163. H CH.sub.3 H CN CH.sub.3 CH.sub.3 164. H Et H CN CH.sub.3 CH.sub.3 165. H CF.sub.3 H CN CH.sub.3 CH.sub.3 166. H OCH.sub.3 H CN CH.sub.3 CH.sub.3 167. H OCF.sub.3 H CN CH.sub.3 CH.sub.3 168. H CN H CN CH.sub.3 CH.sub.3 169. H Br H CN CH.sub.3 Et 170. H I H CN CH.sub.3 Et 171. H CH.sub.3 H CN CH.sub.3 Et 172. H Et H CN CH.sub.3 Et 173. H CF.sub.3 H CN CH.sub.3 Et 174. H OCH.sub.3 H CN CH.sub.3 Et 175. H OCF.sub.3 H CN CH.sub.3 Et 176. H CN H CN CH.sub.3 Et 177. H Br H CN Et Et 178. H I H CN Et Et 179. H CH.sub.3 H CN Et Et 180. H Et H CN Et Et 181. H CF.sub.3 H CN Et Et 182. H OCH.sub.3 H CN Et Et 183. H OCF.sub.3 H CN Et Et 184. H CN H CN Et Et 185. H Br H CN CH.sub.3 Vin 186. H I H CN CH.sub.3 Vin 187. H CH.sub.3 H CN CH.sub.3 Vin 188. H Et H CN CH.sub.3 Vin 189. H CF H CN CH.sub.3 Vin 190. H OCH.sub.3 H CN CH.sub.3 Vin 191. H OCF.sub.3 H CN CH.sub.3 Vin 192. H CN H CN CH.sub.3 Vin 193. H Br H CN Et Vin 194. H I H CN Et Vin 195. H CH.sub.3 H CN Et Vin 196. H Et H CN Et Vin 197. H CF H CN Et Vin 198. H OCH.sub.3 H CN Et Vin 199. H OCF.sub.3 H CN Et Vin 200. H CN H CN Et Vin 201. H H F H CH.sub.3 CH.sub.3 202. H F F H CH.sub.3 CH.sub.3 203. H Cl F H CH.sub.3 CH.sub.3 204. H Br F H CH.sub.3 CH.sub.3 205. H I F H CH.sub.3 CH.sub.3 206. H CH.sub.3 F H CH.sub.3 CH.sub.3 207. H Et F H CH.sub.3 CH.sub.3 208. H CF.sub.3 F H CH.sub.3 CH.sub.3 209. H OCH.sub.3 F H CH.sub.3 CH.sub.3 210. H OCF.sub.3 F H CH.sub.3 CH.sub.3 211. H CN F H CH.sub.3 CH.sub.3 212. H H F H CH.sub.3 Et 213. H F F H CH.sub.3 Et 214. H Cl F H CH.sub.3 Et 215. H Br F H CH.sub.3 Et 216. H I F H CH.sub.3 Et 217. H CH.sub.3 F H CH.sub.3 Et 218. H Et F H CH.sub.3 Et 219. H CF.sub.3 F H CH.sub.3 Et 220. H OCH.sub.3 F H CH.sub.3 Et 221. H OCF.sub.3 F H CH.sub.3 Et 222. H CN F H CH.sub.3 Et 223. H H F H Et Et 224. H F F H Et Et 225. H Cl F H Et Et 226. H Br F H Et Et 227. H I F H Et Et 228. H CH.sub.3 F H Et Et 229. H Et F H Et Et 230. H CF F H Et Et 231. H OCH.sub.3 F H Et Et 232. H OCF.sub.3 F H Et Et 233. H CN F H Et Et 234. H H F H CH.sub.3 Vin 235. H F F H CH.sub.3 Vin 236. H Cl F H CH.sub.3 Vin 237. H Br F H CH.sub.3 Vin 238. H I F H CH.sub.3 Vin 239. H CH.sub.3 F H CH.sub.3 Vin 240. H Et F H CH.sub.3 Vin 241. H CF.sub.3 F H CH.sub.3 Vin 242. H OCH.sub.3 F H CH.sub.3 Vin 243. H OCF.sub.3 F H CH.sub.3 Vin 244. H CN F H CH.sub.3 Vin 245. H H F H Et Vin 246. H F F H Et Vin 247. H Cl F H Et Vin 248. H Br F H Et Vin 249. H I F H Et Vin 250. H CH.sub.3 F H Et Vin 251. H Et F H Et Vin 252. H CF.sub.3 F H Et Vin 253. H OCH.sub.3 F H Et Vin 254. H OCF.sub.3 F H Et Vin 255. H CN F H Et Vin 256. H F F F CH.sub.3 CH.sub.3 257. H Cl F F CH.sub.3 CH.sub.3 258. H Br F F CH.sub.3 CH.sub.3 259. H I F F CH.sub.3 CH.sub.3 260. H CH.sub.3 F F CH.sub.3 CH.sub.3 261. H Et F F CH.sub.3 CH.sub.3 262. H CF.sub.3 F F CH.sub.3 CH.sub.3 263. H OCH.sub.3 F F CH.sub.3 CH.sub.3 264. H OCF.sub.3 F F CH.sub.3 CH.sub.3 265. H CN F F CH.sub.3 CH.sub.3 266. H F F F CH.sub.3 Et 267. H Cl F F CH.sub.3 Et 268. H Br F F CH.sub.3 Et 269. H I F F CH.sub.3 Et 270. H CH.sub.3 F F CH.sub.3 Et 271. H Et F F CH.sub.3 Et 272. H CF.sub.3 F F CH.sub.3 Et 273. H OCH.sub.3 F F CH.sub.3 Et 274. H OCF.sub.3 F F CH.sub.3 Et 275. H CN F F CH.sub.3 Et 276. H F F F Et Et 277. H Cl F F Et Et 278. H Br F F Et Et 279. H I F F Et Et 280. H CH.sub.3 F F Et Et 281. H Et F F Et Et 282. H CF.sub.3 F F Et Et 283. H OCH.sub.3 F F Et Et 284. H OCF.sub.3 F F Et Et 285. H CN F F Et Et 286. H F F F CH Vin 287. H Cl F F CH.sub.3 Vin 288. H Br F F CH.sub.3 Vin 289. H I F F CH.sub.3 Vin 290. H CH.sub.3 F F CH.sub.3 Vin 291. H Et F F CH Vin 292. H CF F F CH.sub.3 Vin 293. H OCH.sub.3 F F CH Vin 294. H OCF.sub.3 F F CH.sub.3 Vin 295. H CN F F CH.sub.3 Vin 296. H F F F Et Vin 297. H Cl F F Et Vin 298. H Br F F Et Vin 299. H I F F Et Vin 300. H CH.sub.3 F F Et Vin 301. H Et F F Et Vin 302. H CF.sub.3 F F Et Vin 303. H OCH.sub.3 F F Et Vin 304. H OCF.sub.3 F F Et Vin 305. H CN F F Et Vin 306. H Cl F Cl CH.sub.3 CH.sub.3 307. H Br F Cl CH.sub.3 CH.sub.3 308. H I F Cl CH.sub.3 CH.sub.3 309. H CH.sub.3 F Cl CH.sub.3 CH.sub.3 310. H Et F Cl CH.sub.3 CH.sub.3 311. H CF.sub.3 F Cl CH.sub.3 CH.sub.3 312. H OCH.sub.3 F Cl CH.sub.3 CH.sub.3 313. H OCF.sub.3 F Cl CH.sub.3 CH.sub.3 314. H CN F Cl CH.sub.3 CH.sub.3 315. H Cl F Cl CH.sub.3 Et 316. H Br F Cl CH.sub.3 Et 317. H I F Cl CH.sub.3 Et 318. H CH.sub.3 F Cl CH.sub.3 Et 319. H Et F Cl CH.sub.3 Et 320. H CF.sub.3 F Cl CH.sub.3 Et 321. H OCH.sub.3 F Cl CH.sub.3 Et 322. H OCF.sub.3 F Cl CH.sub.3 Et 323. H CN F Cl CH.sub.3 Et 324. H Cl F Cl Et Et 325. H Br F Cl Et Et 326. H I F Cl Et Et 327. H CH.sub.3 F Cl Et Et 328. H Et F Cl Et Et 329. H CF.sub.3 F Cl Et Et 330. H OCH.sub.3 F Cl Et Et 331. H OCF.sub.3 F Cl Et Et 332. H CN F Cl Et Et 333. H Cl F Cl CH.sub.3 Vin 334. H Br F Cl CH.sub.3 Vin 335. H I F Cl CH.sub.3 Vin 336. H CH.sub.3 F Cl CH.sub.3 Vin 337. H Et F Cl CH.sub.3 Vin 338. H CF.sub.3 F Cl CH.sub.3 Vin 339. H OCH.sub.3 F Cl CH.sub.3 Vin 340. H OCF.sub.3 F Cl CH.sub.3 Vin 341. H CN F Cl CH.sub.3 Vin 342. H Cl F Cl Et Vin 343. H Br F Cl Et Vin 344. H I F Cl Et Vin 345. H CH.sub.3 F Cl Et Vin 346. H Et F Cl Et Vin 347. H CF.sub.3 F Cl Et Vin 348. H OCH.sub.3 F Cl Et Vin 349. H OCF.sub.3 F Cl Et Vin 350. H CN F Cl Et Vin 351. H Br F Br CH.sub.3 CH.sub.3 352. H Br F Br CH.sub.3 Et 353. H Br F Br Et Et 354. H Br F Br CH.sub.3 Vin 355. H Br F Br Et Vin 356. H I F I CH.sub.3 CH.sub.3 357. H I F I CH.sub.3 Et 358. H I F I Et Et 359. H I F I CH.sub.3 Vin 360. H I F I Et Vin 361. H Br F CN CH.sub.3 CH.sub.3 362. H I F CN CH.sub.3 CH.sub.3 363. H CH.sub.3 F CN CH.sub.3 CH.sub.3 364. H Et F CN CH.sub.3 CH.sub.3 365. H CF.sub.3 F CN CH.sub.3 CH.sub.3 366. H OCH.sub.3 F CN CH.sub.3 CH.sub.3 367. H OCF.sub.3 F CN CH.sub.3 CH.sub.3 368. H CN F CN CH.sub.3 CH.sub.3 369. H Br F CN CH.sub.3 Et 370. H I F CN CH.sub.3 Et 371. H CH.sub.3 F CN CH.sub.3 Et 372. H Et F CN CH.sub.3 Et 373. H CF.sub.3 F CN CH.sub.3 Et 374. H OCH.sub.3 F CN CH.sub.3 Et 375. H OCF.sub.3 F CN CH.sub.3 Et 376. H CN F CN CH.sub.3 Et 377. H Br F CN Et Et 378. H I F CN Et Et 379. H CH.sub.3 F CN Et Et 380. H Et F CN Et Et 381. H CF.sub.3 F CN Et Et 382. H OCH.sub.3 F CN Et Et 383. H OCF.sub.3 F CN Et Et 384. H CN F CN Et Et 385. H Br F CN CH.sub.3 Vin 386. H I F CN CH.sub.3 Vin 387. H CH.sub.3 F CN CH.sub.3 Vin 388. H Et F CN CH.sub.3 Vin 389. H CF.sub.3 F CN CH.sub.3 Vin 390. H OCH.sub.3 F CN CH.sub.3 Vin 391. H OCF.sub.3 F CN CH.sub.3 Vin 392. H CN F CN CH.sub.3 Vin 393. H Br F CN Et Vin 394. H I F CN Et Vin 395. H CH.sub.3 F CN Et Vin 396. H Et F CN Et Vin 397. H CF.sub.3 F CN Et Vin 398. H OCH.sub.3 F CN Et Vin 399. H OCF.sub.3 F CN Et Vin 400. H CN F CN Et Vin 401. H H Cl H CH.sub.3 CH.sub.3 402. H F Cl H CH.sub.3 CH.sub.3 403. H Cl Cl H CH.sub.3 CH.sub.3 404. H Br Cl H CH.sub.3 CH.sub.3 405. H I Cl H CH.sub.3 CH.sub.3 406. H CH.sub.3 Cl H CH.sub.3 CH.sub.3 407. H Et Cl H CH.sub.3 CH.sub.3 408. H CF.sub.3 Cl H CH.sub.3 CH.sub.3 409. H OCH.sub.3 Cl H CH.sub.3 CH.sub.3 410. H OCF.sub.3 Cl H CH.sub.3 CH.sub.3 411. H CN Cl H CH.sub.3 CH.sub.3 412. H H Cl H CH.sub.3 Et 413. H F Cl H CH.sub.3 Et 414. H Cl Cl H CH.sub.3 Et 415. H Br Cl H CH.sub.3 Et 416. H I Cl H CH.sub.3 Et 417. H CH.sub.3 Cl H CH.sub.3 Et 418. H Et Cl H CH.sub.3 Et 419. H CF.sub.3 Cl H CH.sub.3 Et 420. H OCH.sub.3 Cl H CH.sub.3 Et 421. H OCF.sub.3 Cl H CH.sub.3 Et 422. H CN Cl H CH.sub.3 Et 423. H H Cl H Et Et 424. H F Cl H Et Et 425. H Cl Cl H Et Et 426. H Br Cl H Et Et 427. H I Cl H Et Et 428. H CH.sub.3 Cl H Et Et 429. H Et Cl H Et Et 430. H CF.sub.3 Cl H Et Et 431. H OCH.sub.3 Cl H Et Et 432. H OCF.sub.3 Cl H Et Et 433. H CN Cl H Et Et 434. H H Cl H CH.sub.3 Vin 435. H F Cl H CH.sub.3 Vin 436. H Cl Cl H CH.sub.3 Vin 437. H Br Cl H CH.sub.3 Vin 438. H I Cl H CH.sub.3 Vin 439. H CH.sub.3 Cl H CH.sub.3 Vin 440. H Et Cl H CH.sub.3 Vin 441. H CF.sub.3 Cl H CH.sub.3 Vin 442. H OCH.sub.3 Cl H CH.sub.3 Vin 443. H OCF.sub.3 Cl H CH.sub.3 Vin 444. H CN Cl H CH.sub.3 Vin 445. H H Cl H Et Vin 446. H F Cl H Et Vin 447. H Cl Cl H Et Vin 448. H Br Cl H Et Vin 449. H I Cl H Et Vin 450. H CH.sub.3 Cl H Et Vin 451. H Et Cl H Et Vin 452. H CF.sub.3 Cl H Et Vin 453. H OCH.sub.3 Cl H Et Vin 454. H OCF.sub.3 Cl H Et Vin 455. H CN Cl H Et Vin 456. H F Cl F CH.sub.3 CH.sub.3 457. H Cl Cl F CH.sub.3 CH.sub.3 458. H Br Cl F CH.sub.3 CH.sub.3 459. H I Cl F CH.sub.3 CH.sub.3 460. H CH.sub.3 Cl F CH.sub.3 CH.sub.3 461. H Et Cl F CH.sub.3 CH.sub.3 462. H CF.sub.3 Cl F CH.sub.3 CH.sub.3 463. H OCH.sub.3 Cl F CH.sub.3 CH.sub.3 464. H OCF.sub.3 Cl F CH.sub.3 CH.sub.3 465. H CN Cl F CH.sub.3 CH.sub.3 466. H F Cl F CH.sub.3 Et 467. H Cl Cl F CH.sub.3 Et 468. H Br Cl F CH.sub.3 Et 469. H I Cl F CH.sub.3 Et 470. H CH.sub.3 Cl F CH.sub.3 Et 471. H Et Cl F CH.sub.3 Et 472. H CF.sub.3 Cl F CH.sub.3 Et 473. H OCH.sub.3 Cl F CH.sub.3 Et 474. H OCF.sub.3 Cl F CH.sub.3 Et 475. H CN Cl F CH.sub.3 Et 476. H F Cl F Et Et 477. H Cl Cl F Et Et 478. H Br Cl F Et Et 479. H I Cl F Et Et 480. H CH.sub.3 Cl F Et Et 481. H Et Cl F Et Et 482. H CF.sub.3 Cl F Et Et 483. H OCH.sub.3 Cl F Et Et 484. H OCF.sub.3 Cl F Et Et 485. H CN Cl F Et Et 486. H F Cl F CH.sub.3 Vin 487. H Cl Cl F CH.sub.3 Vin 488. H Br Cl F CH.sub.3 Vin 489. H I Cl F CH.sub.3 Vin 490. H CH.sub.3 Cl F CH.sub.3 Vin 491. H Et Cl F CH.sub.3 Vin 492. H CF.sub.3 Cl F CH.sub.3 Vin 493. H OCH.sub.3 Cl F CH.sub.3 Vin 494. H OCF.sub.3 Cl F CH.sub.3 Vin 495. H CN Cl F CH.sub.3 Vin 496. H F Cl F Et Vin 497. H Cl Cl F Et Vin 498. H Br Cl F Et Vin 499. H I Cl F Et Vin 500. H CH.sub.3 Cl F Et Vin 501. H Et Cl F Et Vin 502. H CF.sub.3 Cl F Et Vin 503. H OCH.sub.3 Cl F Et Vin 504. H OCF.sub.3 Cl F Et Vin 505. H CN Cl F Et Vin 506. H Cl Cl Cl CH.sub.3 CH.sub.3 507. H Br Cl Cl CH.sub.3 CH.sub.3 508. H I Cl Cl CH.sub.3 CH.sub.3 509. H CH.sub.3 Cl Cl CH.sub.3 CH.sub.3 510. H Et Cl Cl CH.sub.3 CH.sub.3 511. H CF.sub.3 Cl Cl CH.sub.3 CH.sub.3 512. H OCH.sub.3 Cl Cl CH.sub.3 CH.sub.3 513. H OCF.sub.3 Cl Cl CH.sub.3 CH.sub.3 514. H CN Cl Cl CH.sub.3 CH.sub.3 515. H Cl Cl Cl CH.sub.3 Et 516. H Br Cl Cl CH.sub.3 Et 517. H I Cl Cl CH.sub.3 Et 518. H CH.sub.3 Cl Cl CH.sub.3 Et 519. H Et Cl Cl CH.sub.3 Et 520. H CF.sub.3 Cl Cl CH.sub.3 Et 521. H OCH.sub.3 Cl Cl CH.sub.3 Et 522. H OCF.sub.3 Cl Cl CH.sub.3 Et 523. H CN Cl Cl CH.sub.3 Et 524. H Cl Cl Cl Et Et 525. H Br Cl Cl Et Et 526. H I Cl Cl Et Et 527. H CH.sub.3 Cl Cl Et Et 528. H Et Cl Cl Et Et 529. H CF.sub.3 Cl Cl Et Et 530. H OCH.sub.3 Cl Cl Et Et 531. H OCF.sub.3 Cl Cl Et Et 532. H CN Cl Cl Et Et 533. H Cl Cl Cl CH.sub.3 Vin 534. H Br Cl Cl CH.sub.3 Vin 535. H I Cl Cl CH.sub.3 Vin 536. H CH.sub.3 Cl Cl CH.sub.3 Vin 537. H Et Cl Cl CH.sub.3 Vin 538. H CF.sub.3 Cl Cl CH.sub.3 Vin 539. H OCH.sub.3 Cl Cl CH.sub.3 Vin 540. H OCF.sub.3 Cl Cl CH.sub.3 Vin 541. H CN Cl Cl CH.sub.3 Vin 542. H Cl Cl Cl Et Vin 543. H Br Cl Cl Et Vin 544. H I Cl Cl Et Vin 545. H CH.sub.3 Cl Cl Et Vin 546. H Et Cl Cl Et Vin 547. H CF.sub.3 Cl Cl Et Vin 548. H OCH.sub.3 Cl Cl Et Vin 549. H OCF.sub.3 Cl Cl Et Vin 550. H CN Cl Cl Et Vin 551. H Br Cl Br CH.sub.3 CH.sub.3 552. H Br Cl Br CH.sub.3 Et 553. H Br Cl Br Et Et 554. H Br Cl Br CH.sub.3 Vin 555. H Br Cl Br Et Vin 556. H I Cl I CH.sub.3 CH.sub.3 557. H I Cl I CH.sub.3 Et 558. H I Cl I Et Et 559. H I Cl I CH.sub.3 Vin 560. H I Cl I Et Vin 561. H Br Cl CN CH.sub.3 CH.sub.3 562. H I Cl CN CH.sub.3 CH.sub.3 563. H CH.sub.3 Cl CN CH.sub.3 CH.sub.3 564. H Et Cl CN CH.sub.3 CH.sub.3 565. H CF.sub.3 Cl CN CH.sub.3 CH.sub.3 566. H OCH.sub.3 Cl CN CH.sub.3 CH.sub.3 567. H OCF.sub.3 Cl CN CH.sub.3 CH.sub.3 568. H CN Cl CN CH.sub.3 CH.sub.3 569. H Br Cl CN CH.sub.3 Et 570. H I Cl CN CH.sub.3 Et 571. H CH.sub.3 Cl CN CH.sub.3 Et 572. H Et Cl CN CH.sub.3 Et 573. H CF.sub.3 Cl CN CH.sub.3 Et 574. H OCH.sub.3 Cl CN CH.sub.3 Et 575. H OCF.sub.3 Cl CN CH.sub.3 Et 576. H CN Cl CN CH.sub.3 Et 577. H Br Cl CN Et Et 578. H I Cl CN Et Et 579. H CH.sub.3 Cl CN Et Et 580. H Et Cl CN Et Et 581. H CF.sub.3 Cl CN Et Et 582. H OCH.sub.3 Cl CN Et Et 583. H OCF.sub.3 Cl CN Et Et 584. H CN Cl CN Et Et 585. H Br Cl CN CH.sub.3 Vin 586. H I Cl CN CH.sub.3 Vin 587. H CH.sub.3 Cl CN CH.sub.3 Vin 588. H Et Cl CN CH.sub.3 Vin 589. H CF.sub.3 Cl CN CH.sub.3 Vin 590. H OCH.sub.3 Cl CN CH.sub.3 Vin 591. H OCF.sub.3 Cl CN CH.sub.3 Vin 592. H CN Cl CN CH.sub.3 Vin 593. H Br Cl CN Et Vin 594. H I Cl CN Et Vin 595. H CH.sub.3 Cl CN Et Vin 596. H Et Cl CN Et Vin 597. H CF.sub.3 Cl CN Et Vin 598. H OCH.sub.3 Cl CN Et Vin 599. H OCF.sub.3 Cl CN Et Vin 600. H CN Cl CN Et Vin 601. F H H H CH.sub.3 CH.sub.3 602. F F H H CH.sub.3 CH.sub.3 603. F Cl H H CH.sub.3 CH.sub.3 604. F Br H H CH.sub.3 CH.sub.3 605. F I H H CH.sub.3 CH.sub.3 606. F CH.sub.3 H H CH.sub.3 CH.sub.3 607. F Et H H CH.sub.3 CH 608. F CF.sub.3 H H CH.sub.3 CH.sub.3 609. F OCH.sub.3 H H CH.sub.3 CH.sub.3 610. F OCF.sub.3 H H CH.sub.3 CH.sub.3 611. F CN H H CH.sub.3 CH.sub.3 612. F H H H CH.sub.3 Et 613. F F H H CH.sub.3 Et 614. F Cl H H CH.sub.3 Et 615. F Br H H CH.sub.3 Et 616. F I H H CH.sub.3 Et 617. F CH.sub.3 H H CH.sub.3 Et 618. F Et H H CH.sub.3 Et 619. F CF.sub.3 H H CH.sub.3 Et 620. F OCH.sub.3 H H CH.sub.3 Et 621. F OCF.sub.3 H H CH.sub.3 Et 622. F CN H H CH.sub.3 Et 623. F H H H Et Et 624. F F H H Et Et 625. F Cl H H Et Et 626. F Br H H Et Et 627. F I H H Et Et 628. F CH.sub.3 H H Et Et 629. F Et H H Et Et 630. F CF.sub.3 H H Et Et 631. F OCH.sub.3 H H Et Et 632. F OCF.sub.3 H H Et Et 633. F CN H H Et Et 634. F H H H CH.sub.3 Vin 635. F F H H CH.sub.3 Vin 636. F Cl H H CH.sub.3 Vin 637. F Br H H CH.sub.3 Vin 638. F I H H CH.sub.3 Vin 639. F CH.sub.3 H H CH.sub.3 Vin 640. F Et H H CH.sub.3 Vin 641. F CF.sub.3 H H CH.sub.3 Vin 642. F OCH.sub.3 H H CH.sub.3 Vin 643. F OCF.sub.3 H H CH.sub.3 Vin 644. F CN H H CH.sub.3 Vin 645. F H H H Et Vin 646. F F H H Et Vin 647. F Cl H H Et Vin 648. F Br H H Et Vin 649. F I H H Et Vin 650. F CH.sub.3 H H Et Vin 651. F Et H H Et Vin 652. F CF.sub.3 H H Et Vin 653. F OCH.sub.3 H H Et Vin 654. F OCF.sub.3 H H Et Vin 655. F CN H H Et Vin 656. F H H F CH.sub.3 CH.sub.3 657. F F H F CH.sub.3 CH.sub.3 658. F Cl H F CH.sub.3 CH.sub.3 659. F Br H F CH.sub.3 CH.sub.3 660. F I H F CH.sub.3 CH.sub.3 661. F CH.sub.3 H F CH.sub.3 CH.sub.3 662. F Et H F CH.sub.3 CH.sub.3 663. F CF.sub.3 H F CH.sub.3 CH.sub.3 664. F OCH.sub.3 H F CH.sub.3 CH.sub.3 665. F OCF.sub.3 H F CH.sub.3 CH.sub.3 666. F CN H F CH.sub.3 CH.sub.3 667. F H H F CH.sub.3 Et 668. F F H F CH.sub.3 Et 669. F Cl H F CH.sub.3 Et 670. F Br H F CH.sub.3 Et 671. F I H F CH.sub.3 Et 672. F CH.sub.3 H F CH.sub.3 Et 673. F Et H F CH.sub.3 Et 674. F CF.sub.3 H F CH.sub.3 Et 675. F OCH.sub.3 H F CH.sub.3 Et 676. F OCF.sub.3 H F CH.sub.3 Et 677. F CN H F CH.sub.3 Et 678. F H H F Et Et 679. F F H F Et Et 680. F Cl H F Et Et 681. F Br H F Et Et 682. F I H F Et Et 683. F CH.sub.3 H F Et Et 684. F Et H F Et Et 685. F CF.sub.3 H F Et Et 686. F OCH.sub.3 H F Et Et 687. F OCF.sub.3 H F Et Et 688. F CN H F Et Et 689. F H H F CH.sub.3 Vin 690. F F H F CH.sub.3 Vin 691. F Cl H F CH.sub.3 Vin 692. F Br H F CH.sub.3 Vin 693. F I H F CH.sub.3 Vin 694. F CH.sub.3 H F CH.sub.3 Vin 695. F Et H F CH.sub.3 Vin 696. F CF.sub.3 H F CH.sub.3 Vin 697. F OCH.sub.3 H F CH.sub.3 Vin 698. F OCF.sub.3 H F CH.sub.3 Vin 699. F CN H F CH.sub.3 Vin 700. F H H F Et Vin 701. F F H F Et Vin 702. F Cl H F Et Vin 703. F Br H F Et Vin 704. F I H F Et Vin 705. F CH.sub.3 H F Et Vin 706. F Et H F Et Vin 707. F CF.sub.3 H F Et Vin 708. F OCH.sub.3 H F Et Vin 709. F OCF.sub.3 H F Et Vin 710. F CN H F Et Vin 711. F H H Cl CH.sub.3 CH.sub.3 712. F F H Cl CH.sub.3 CH.sub.3 713. F Cl H Cl CH.sub.3 CH.sub.3 714. F Br H Cl CH.sub.3 CH.sub.3 715. F I H Cl CH.sub.3 CH.sub.3 716. F CH.sub.3 H Cl CH.sub.3 CH.sub.3 717. F Et H Cl CH.sub.3 CH.sub.3 718. F CF.sub.3 H Cl CH.sub.3 CH.sub.3 719. F OCH.sub.3 H Cl CH.sub.3 CH.sub.3 720. F OCF.sub.3 H Cl CH.sub.3 CH.sub.3 721. F CN H Cl CH.sub.3 CH.sub.3 722. F H H Cl CH.sub.3 Et 723. F F H Cl CH.sub.3 Et 724. F Cl H Cl CH.sub.3 Et 725. F Br H Cl CH.sub.3 Et 726. F I H Cl CH.sub.3 Et 727. F CH.sub.3 H Cl CH.sub.3 Et 728. F Et H Cl CH.sub.3 Et 729. F CF.sub.3 H Cl CH.sub.3 Et 730. F OCH.sub.3 H Cl CH.sub.3 Et 731. F OCF.sub.3 H Cl CH.sub.3 Et 732. F CN H Cl CH.sub.3 Et 733. F H H Cl Et Et 734. F F H Cl Et Et 735. F Cl H Cl Et Et 736. F Br H Cl Et Et 737. F I H Cl Et Et 738. F CH.sub.3 H Cl Et Et 739. F Et H Cl Et Et 740. F CF.sub.3 H Cl Et Et 741. F OCH.sub.3 H Cl Et Et 742. F OCF.sub.3 H Cl Et Et 743. F CN H Cl Et Et 744. F H H Cl CH.sub.3 Vin 745. F F H Cl CH.sub.3 Vin 746. F Cl H Cl CH.sub.3 Vin 747. F Br H Cl CH.sub.3 Vin 748. F I H Cl CH.sub.3 Vin 749. F CH.sub.3 H Cl CH.sub.3 Vin 750. F Et H Cl CH.sub.3 Vin 751. F CF.sub.3 H Cl CH.sub.3 Vin 752. F OCH.sub.3 H Cl CH.sub.3 Vin 753. F OCF.sub.3 H Cl CH.sub.3 Vin 754. F CN H Cl CH.sub.3 Vin 755. F H H Cl Et Vin 756. F F H Cl Et Vin 757. F Cl H Cl Et Vin 758. F Br H Cl Et Vin 759. F I H Cl Et Vin 760. F CH.sub.3 H Cl Et Vin 761. F Et H Cl Et Vin 762. F CF.sub.3 H Cl Et Vin 763. F OCH.sub.3 H Cl Et Vin 764. F OCF.sub.3 H Cl Et Vin 765. F CN H Cl Et Vin 766. F Br H Br CH.sub.3 CH.sub.3 767. F Br H Br CH.sub.3 Et 768. F Br H Br Et Et 769. F Br H Br CH.sub.3 Vin 770. F Br H Br Et Vin 771. F I H I CH.sub.3 CH.sub.3 772. F I H I CH.sub.3 Et 773. F I H I Et Et 774. F I H I CH.sub.3 Vin 775. F I H I Et Vin 776. F H H CN CH.sub.3 CH.sub.3 777. F F H CN CH.sub.3 CH.sub.3 778. F Cl H CN CH.sub.3 CH.sub.3 779. F Br H CN CH.sub.3 CH.sub.3 780. F I H CN CH.sub.3 CH.sub.3 781. F CH.sub.3 H CN CH.sub.3 CH.sub.3 782. F Et H CN CH.sub.3 CH.sub.3 783. F CF.sub.3 H CN CH.sub.3 CH.sub.3 784. F OCH.sub.3 H CN CH.sub.3 CH.sub.3 785. F OCF.sub.3 H CN CH.sub.3 CH.sub.3 786. F CN H CN CH.sub.3 CH.sub.3 787. F H H CN CH.sub.3 Et 788. F F H CN CH.sub.3 Et 789. F Cl H CN CH.sub.3 Et 790. F Br H CN CH.sub.3 Et 791. F I H CN CH.sub.3 Et 792. F CH.sub.3 H CN CH.sub.3 Et 793. F Et H CN CH.sub.3 Et 794. F CF.sub.3 H CN CH.sub.3 Et 795. F OCH.sub.3 H CN CH.sub.3 Et 796. F OCF.sub.3 H CN CH.sub.3 Et 797. F CN H CN CH.sub.3 Et 798. F H H CN Et Et 799. F F H CN Et Et 800. F Cl H CN Et Et 801. F Br H CN Et Et 802. F I H CN Et Et 803. F CH.sub.3 H CN Et Et 804. F Et H CN Et Et 805. F CF.sub.3 H CN Et Et 806. F OCH.sub.3 H CN Et Et 807. F OCF.sub.3 H CN Et Et 808. F CN H CN Et Et 809. F H H CN CH.sub.3 Vin 810. F F H CN CH.sub.3 Vin 811. F Cl H CN CH.sub.3 Vin 812. F Br H CN CH.sub.3 Vin 813. F I H CN CH.sub.3 Vin 814. F CH.sub.3 H CN CH.sub.3 Vin 815. F Et H CN CH.sub.3 Vin 816. F CF.sub.3 H CN CH.sub.3 Vin 817. F OCH.sub.3 H CN CH.sub.3 Vin 818. F OCF.sub.3 H CN CH.sub.3 Vin 819. F CN H CN CH.sub.3 Vin 820. F H H CN Et Vin 821. F F H CN Et Vin 822. F Cl H CN Et Vin 823. F Br H CN Et Vin 824. F I H CN Et Vin 825. F CH.sub.3 H CN Et Vin 826. F Et H CN Et Vin 827. F CF.sub.3 H CN Et Vin 828. F OCH.sub.3 H CN Et Vin 829. F OCF.sub.3 H CN Et Vin 830. F CN H CN Et Vin 831. F H F H CH.sub.3 CH.sub.3 832. F F F H CH.sub.3 CH.sub.3 833. F Cl F H CH.sub.3 CH.sub.3 834. F Br F H CH.sub.3 CH.sub.3 835. F I F H CH.sub.3 CH.sub.3 836. F CH.sub.3 F H CH.sub.3 CH.sub.3 837. F Et F H CH.sub.3 CH.sub.3 838. F CF.sub.3 F H CH.sub.3 CH.sub.3 839. F OCH.sub.3 F H CH.sub.3 CH.sub.3 840. F OCF.sub.3 F H CH.sub.3 CH.sub.3 841. F CN F H CH.sub.3 CH.sub.3 842. F H F H CH.sub.3 Et 843. F F F H CH.sub.3 Et 844. F Cl F H CH.sub.3 Et 845. F Br F H CH.sub.3 Et 846. F I F H CH.sub.3 Et 847. F CH.sub.3 F H CH.sub.3 Et 848. F Et F H CH.sub.3 Et 849. F CF.sub.3 F H CH.sub.3 Et 850. F OCH.sub.3 F H CH.sub.3 Et 851. F OCF.sub.3 F H CH.sub.3 Et 852. F CN F H CH.sub.3 Et 853. F H F H Et Et 854. F F F H Et Et 855. F Cl F H Et Et 856. F Br F H Et Et 857. F I F H Et Et 858. F CH.sub.3 F H Et Et 859. F Et F H Et Et 860. F CF.sub.3 F H Et Et 861. F OCH.sub.3 F H Et Et 862. F OCF.sub.3 F H Et Et 863. F CN F H Et Et 864. F H F H CH.sub.3 Vin 865. F F F H CH.sub.3 Vin 866. F Cl F H CH.sub.3 Vin 867. F Br F H CH.sub.3 Vin 868. F I F H CH.sub.3 Vin 869. F CH.sub.3 F H CH.sub.3 Vin 870. F Et F H CH.sub.3 Vin 871. F CF.sub.3 F H CH.sub.3 Vin 872. F OCH.sub.3 F H CH.sub.3 Vin 873. F OCF.sub.3 F H CH.sub.3 Vin 874. F CN F H CH.sub.3 Vin 875. F H F H Et Vin 876. F F F H Et Vin 877. F Cl F H Et Vin 878. F Br F H Et Vin 879. F I F H Et Vin 880. F CH.sub.3 F H Et Vin 881. F Et F H Et Vin 882. F CF.sub.3 F H Et Vin 883. F OCH.sub.3 F H Et Vin 884. F OCF.sub.3 F H Et Vin 885. F CN F H Et Vin 886. F H F F CH.sub.3 CH.sub.3 887. F F F F CH.sub.3 CH.sub.3 888. F Cl F F CH.sub.3 CH.sub.3 889. F Br F F CH.sub.3 CH.sub.3 890. F I F F CH.sub.3 CH.sub.3 891. F CH.sub.3 F F CH.sub.3 CH.sub.3 892. F Et F F CH.sub.3 CH.sub.3 893. F CF.sub.3 F F CH.sub.3 CH.sub.3 894. F OCH.sub.3 F F CH.sub.3 CH.sub.3 895. F OCF.sub.3 F F CH.sub.3 CH.sub.3 896. F CN F F CH.sub.3 CH.sub.3 897. F H F F CH.sub.3 Et 898. F F F F CH.sub.3 Et 899. F Cl F F CH.sub.3 Et 900. F Br F F CH.sub.3 Et 901. F I F F CH.sub.3 Et 902. F CH.sub.3 F F CH.sub.3 Et 903. F Et F F CH.sub.3 Et 904. F CF.sub.3 F F CH.sub.3 Et 905. F OCH.sub.3 F F CH.sub.3 Et 906. F OCF.sub.3 F F CH.sub.3 Et 907. F CN F F CH.sub.3 Et 908. F H F F Et Et 909. F F F F Et Et 910. F Cl F F Et Et 911. F Br F F Et Et 912. F I F F Et Et 913. F CH.sub.3 F F Et Et 914. F Et F F Et Et 915. F CF.sub.3 F F Et Et 916. F OCH.sub.3 F F Et Et 917. F OCF.sub.3 F F Et Et 918. F CN F F Et Et 919. F H F F CH.sub.3 Vin 920. F F F F CH.sub.3 Vin 921. F Cl F F CH.sub.3 Vin 922. F Br F F CH.sub.3 Vin 923. F I F F CH.sub.3 Vin 924. F CH.sub.3 F F CH.sub.3 Vin 925. F Et F F CH.sub.3 Vin 926. F CF.sub.3 F F CH.sub.3 Vin 927. F OCH.sub.3 F F CH.sub.3 Vin 928. F OCF.sub.3 F F CH.sub.3 Vin 929. F CN F F CH.sub.3 Vin 930. F H F F Et Vin 931. F F F F Et Vin 932. F Cl F F Et Vin 933. F Br F F Et Vin 934. F I F F Et Vin 935. F CH.sub.3 F F Et Vin 936. F Et F F Et Vin 937. F CF.sub.3 F F Et Vin 938. F OCH.sub.3 F F Et Vin 939. F OCF.sub.3 F F Et Vin 940. F CN F F Et Vin 941. F H F Cl CH.sub.3 CH.sub.3 942. F F F Cl CH.sub.3 CH.sub.3 943. F Cl F Cl CH.sub.3 CH.sub.3 944. F Br F Cl CH.sub.3 CH.sub.3 945. F I F Cl CH.sub.3 CH.sub.3 946. F CH.sub.3 F Cl CH.sub.3 CH.sub.3 947. F Et F Cl CH.sub.3 CH.sub.3 948. F CF.sub.3 F Cl CH.sub.3 CH.sub.3 949. F OCH.sub.3 F Cl CH.sub.3 CH.sub.3 950. F OCF.sub.3 F Cl CH.sub.3 CH.sub.3 951. F CN F Cl CH.sub.3 CH.sub.3 952. F H F Cl CH.sub.3 Et 953. F F F Cl CH.sub.3 Et 954. F Cl F Cl CH.sub.3 Et 955. F Br F Cl CH.sub.3 Et 956. F I F Cl CH.sub.3 Et 957. F CH.sub.3 F Cl CH.sub.3 Et 958. F Et F Cl CH.sub.3 Et 959. F CF.sub.3 F Cl CH.sub.3 Et 960. F OCH.sub.3 F Cl CH.sub.3 Et 961. F OCF.sub.3 F Cl CH.sub.3 Et 962. F CN F Cl CH.sub.3 Et 963. F H F Cl Et Et 964. F F F Cl Et Et 965. F Cl F Cl Et Et 966. F Br F Cl Et Et 967. F I F Cl Et Et 968. F CH.sub.3 F Cl Et Et 969. F Et F Cl Et Et 970. F CF.sub.3 F Cl Et Et 971. F OCH.sub.3 F Cl Et Et 972. F OCF.sub.3 F Cl Et Et 973. F CN F Cl Et Et 974. F H F Cl CH.sub.3 Vin 975. F F F Cl CH.sub.3 Vin 976. F Cl F Cl CH.sub.3 Vin 977. F Br F Cl CH.sub.3 Vin 978. F I F Cl CH.sub.3 Vin 979. F CH.sub.3 F Cl CH.sub.3 Vin 980. F Et F Cl CH.sub.3 Vin 981. F CF.sub.3 F Cl CH.sub.3 Vin 982. F OCH.sub.3 F Cl CH.sub.3 Vin 983. F OCF.sub.3 F Cl CH.sub.3 Vin 984. F CN F Cl CH.sub.3 Vin 985. F H F Cl Et Vin 986. F F F Cl Et Vin 987. F Cl F Cl Et Vin 988. F Br F Cl Et Vin 989. F I F Cl Et Vin 990. F CH.sub.3 F Cl Et Vin 991. F Et F Cl Et Vin 992. F CF.sub.3 F Cl Et Vin 993. F OCH.sub.3 F Cl Et Vin 994. F OCF.sub.3 F Cl Et Vin 995. F CN F Cl Et Vin 996. F Br F Br CH.sub.3 CH.sub.3 997. F Br F Br CH.sub.3 Et 998. F Br F Br Et Et 999. F Br F Br CH.sub.3 Vin 1000. F Br F Br Et Vin 1001. F I F I CH.sub.3 CH.sub.3 1002. F I F I CH.sub.3 Et 1003. F I F I Et Et 1004. F I F I CH.sub.3 Vin 1005. F I F I Et Vin 1006. F H F CN CH.sub.3 CH.sub.3 1007. F F F CN CH.sub.3 CH.sub.3 1008. F Cl F CN CH.sub.3 CH.sub.3 1009. F Br F CN CH.sub.3 CH.sub.3 1010. F I F CN CH.sub.3 CH.sub.3 1011. F CH.sub.3 F CN CH.sub.3 CH.sub.3 1012. F Et F CN CH.sub.3 CH.sub.3 1013. F CF.sub.3 F CN CH.sub.3 CH.sub.3 1014. F OCH.sub.3 F CN CH.sub.3 CH.sub.3 1015. F OCF.sub.3 F CN CH.sub.3 CH.sub.3 1016. F CN F CN CH.sub.3 CH.sub.3 1017. F H F CN CH.sub.3 Et 1018. F F F CN CH.sub.3 Et 1019. F Cl F CN CH.sub.3 Et 1020. F Br F CN CH.sub.3 Et 1021. F I F CN CH.sub.3 Et 1022. F CH.sub.3 F CN CH.sub.3 Et 1023. F Et F CN CH.sub.3 Et 1024. F CF.sub.3 F CN CH.sub.3 Et 1025. F OCH.sub.3 F CN CH.sub.3 Et 1026. F OCF.sub.3 F CN CH.sub.3 Et 1027. F CN F CN CH.sub.3 Et 1028. F H F CN Et Et 1029. F F F CN Et Et 1030. F Cl F CN Et Et 1031. F Br F CN Et Et 1032. F I F CN Et Et 1033. F CH.sub.3 F CN Et Et 1034. F Et F CN Et Et 1035. F CF.sub.3 F CN Et Et 1036. F OCH.sub.3 F CN Et Et 1037. F OCF.sub.3 F CN Et Et 1038. F CN F CN Et Et 1039. F H F CN CH.sub.3 Vin 1040. F F F CN CH.sub.3 Vin 1041. F Cl F CN CH.sub.3 Vin 1042. F Br F CN CH.sub.3 Vin 1043. F I F CN CH.sub.3 Vin 1044. F CH.sub.3 F CN CH.sub.3 Vin 1045. F Et F CN CH.sub.3 Vin 1046. F CF.sub.3 F CN CH.sub.3 Vin 1047. F OCH.sub.3 F CN CH.sub.3 Vin 1048. F OCF.sub.3 F CN CH.sub.3 Vin 1049. F CN F CN CH.sub.3 Vin 1050. F H F CN Et Vin 1051. F F F CN Et Vin 1052. F Cl F CN Et Vin 1053. F Br F CN Et Vin 1054. F I F CN Et Vin 1055. F CH.sub.3 F CN Et Vin 1056. F Et F CN Et Vin 1057. F CF.sub.3 F CN Et Vin 1058. F OCH.sub.3 F CN Et Vin 1059. F OCF.sub.3 F CN Et Vin 1060. F CN F CN Et Vin 1061. F H Cl H CH.sub.3 CH.sub.3 1062. F F Cl H CH.sub.3 CH.sub.3 1063. F Cl Cl H CH.sub.3 CH.sub.3 1064. F Br Cl H CH.sub.3 CH.sub.3 1065. F I Cl H CH.sub.3 CH.sub.3 1066. F CH.sub.3 Cl H CH.sub.3 CH.sub.3 1067. F Et Cl H CH.sub.3 CH.sub.3 1068. F CF.sub.3 Cl H CH.sub.3 CH.sub.3 1069. F OCH.sub.3 Cl H CH.sub.3 CH.sub.3 1070. F OCF.sub.3 Cl H CH.sub.3 CH.sub.3 1071. F CN Cl H CH.sub.3 CH.sub.3 1072. F H Cl H CH.sub.3 Et 1073. F F Cl H CH.sub.3 Et 1074. F Cl Cl H CH.sub.3 Et 1075. F Br Cl H CH.sub.3 Et 1076. F I Cl H CH.sub.3 Et 1077. F CH.sub.3 Cl H CH.sub.3 Et 1078. F Et Cl H CH.sub.3 Et 1079. F CF.sub.3 Cl H CH.sub.3 Et 1080. F OCH.sub.3 Cl H CH.sub.3 Et 1081. F OCF.sub.3 Cl H CH.sub.3 Et 1082. F CN Cl H CH.sub.3 Et 1083. F H Cl H Et Et 1084. F F Cl H Et Et 1085. F Cl Cl H Et Et 1086. F Br Cl H Et Et 1087. F I Cl H Et Et 1088. F CH.sub.3 Cl H Et Et 1089. F Et Cl H Et Et 1090. F CF.sub.3 Cl H Et Et 1091. F OCH.sub.3 Cl H Et Et 1092. F OCF.sub.3 Cl H Et Et 1093. F CN Cl H Et Et 1094. F H Cl H CH.sub.3 Vin 1095. F F Cl H CH.sub.3 Vin 1096. F Cl Cl H CH.sub.3 Vin 1097. F Br Cl H CH.sub.3 Vin 1098. F I Cl H CH.sub.3 Vin 1099. F CH.sub.3 Cl H CH.sub.3 Vin 1100. F Et Cl H CH.sub.3 Vin 1101. F CF.sub.3 Cl H CH.sub.3 Vin 1102. F OCH.sub.3 Cl H CH.sub.3 Vin 1103. F OCF.sub.3 Cl H CH.sub.3 Vin 1104. F CN Cl H CH.sub.3 Vin 1105. F H Cl H Et Vin 1106. F F Cl H Et Vin 1107. F Cl Cl H Et Vin 1108. F Br Cl H Et Vin 1109. F I Cl H Et Vin 1110. F CH.sub.3 Cl H Et Vin 1111. F Et Cl H Et Vin 1112. F CF.sub.3 Cl H Et Vin 1113. F OCH.sub.3 Cl H Et Vin 1114. F OCF.sub.3 Cl H Et Vin 1115. F CN Cl H Et Vin 1116. F H Cl F CH.sub.3 CH.sub.3 1117. F F Cl F CH.sub.3 CH.sub.3 1118. F Cl Cl F CH.sub.3 CH.sub.3 1119. F Br Cl F CH.sub.3 CH.sub.3 1120. F I Cl F CH.sub.3 CH.sub.3 1121. F CH.sub.3 Cl F CH.sub.3 CH.sub.3 1122. F Et Cl F CH.sub.3 CH.sub.3 1123. F CF.sub.3 Cl F CH.sub.3 CH.sub.3 1124. F OCH.sub.3 Cl F CH.sub.3 CH.sub.3 1125. F OCF.sub.3 Cl F CH.sub.3 CH.sub.3 1126. F CN Cl F CH.sub.3 CH.sub.3 1127. F H Cl F CH.sub.3 Et 1128. F F Cl F CH.sub.3 Et 1129. F Cl Cl F CH.sub.3 Et 1130. F Br Cl F CH.sub.3 Et 1131. F I Cl F CH.sub.3 Et 1132. F CH.sub.3 Cl F CH.sub.3 Et 1133. F Et Cl F CH.sub.3 Et 1134. F CF.sub.3 Cl F CH.sub.3 Et 1135. F OCH.sub.3 Cl F CH.sub.3 Et 1136. F OCF.sub.3 Cl F CH.sub.3 Et 1137. F CN Cl F CH.sub.3 Et 1138. F H Cl F Et Et 1139. F F Cl F Et Et 1140. F Cl Cl F Et Et 1141. F Br Cl F Et Et 1142. F I Cl F Et Et 1143. F CH.sub.3 Cl F Et Et 1144. F Et Cl F Et Et 1145. F CF.sub.3 Cl F Et Et 1146. F OCH.sub.3 Cl F Et Et 1147. F OCF.sub.3 Cl F Et Et 1148. F CN Cl F Et Et 1149. F H Cl F CH.sub.3 Vin 1150. F F Cl F CH.sub.3 Vin 1151. F Cl Cl F CH.sub.3 Vin 1152. F Br Cl F CH.sub.3 Vin 1153. F I Cl F CH.sub.3 Vin 1154. F CH.sub.3 Cl F CH.sub.3 Vin 1155. F Et Cl F CH.sub.3 Vin 1156. F CF.sub.3 Cl F CH.sub.3 Vin 1157. F OCH.sub.3 Cl F CH.sub.3 Vin 1158. F OCF.sub.3 Cl F CH.sub.3 Vin 1159. F CN Cl F CH.sub.3 Vin 1160. F H Cl F Et Vin 1161. F F Cl F Et Vin 1162. F Cl Cl F Et Vin 1163. F Br Cl F Et Vin 1164. F I Cl F Et Vin 1165. F CH.sub.3 Cl F Et Vin 1166. F Et Cl F Et Vin 1167. F CF.sub.3 Cl F Et Vin 1168. F OCH.sub.3 Cl F Et Vin 1169. F OCF.sub.3 Cl F Et Vin 1170. F CN Cl F Et Vin 1171. F H Cl Cl CH.sub.3 CH.sub.3 1172. F F Cl Cl CH.sub.3 CH.sub.3 1173. F Cl Cl Cl CH.sub.3 CH.sub.3 1174. F Br Cl Cl CH.sub.3 CH.sub.3 1175. F I Cl Cl CH.sub.3 CH.sub.3 1176. F CH.sub.3 Cl Cl CH.sub.3 CH.sub.3 1177. F Et Cl Cl CH.sub.3 CH.sub.3 1178. F CF.sub.3 Cl Cl CH.sub.3 CH.sub.3 1179. F OCH.sub.3 Cl Cl CH.sub.3 CH.sub.3 1180. F OCF.sub.3 Cl Cl CH.sub.3 CH.sub.3 1181. F CN Cl Cl CH.sub.3 CH.sub.3 1182. F H Cl Cl CH.sub.3 Et 1183. F F Cl Cl CH.sub.3 Et 1184. F Cl Cl Cl CH.sub.3 Et 1185. F Br Cl Cl CH.sub.3 Et 1186. F I Cl Cl CH.sub.3 Et 1187. F CH.sub.3 Cl Cl CH.sub.3 Et 1188. F Et Cl Cl CH.sub.3 Et 1189. F CF.sub.3 Cl Cl CH.sub.3 Et 1190. F OCH.sub.3 Cl Cl CH.sub.3 Et 1191. F OCF.sub.3 Cl Cl CH.sub.3 Et 1192. F CN Cl Cl CH.sub.3 Et 1193. F H Cl Cl Et Et 1194. F F Cl Cl Et Et 1195. F Cl Cl Cl Et Et 1196. F Br Cl Cl Et Et 1197. F I Cl Cl Et Et 1198. F CH.sub.3 Cl Cl Et Et 1199. F Et Cl Cl Et Et 1200. F CF.sub.3 Cl Cl Et Et 1201. F OCH.sub.3 Cl Cl Et Et 1202. F OCF.sub.3 Cl Cl Et Et 1203. F CN Cl Cl Et Et 1204. F H Cl Cl CH.sub.3 Vin 1205. F F Cl Cl CH.sub.3 Vin 1206. F Cl Cl Cl CH.sub.3 Vin 1207. F Br Cl Cl CH.sub.3 Vin 1208. F I Cl Cl CH.sub.3 Vin 1209. F CH.sub.3 Cl Cl CH.sub.3 Vin 1210. F Et Cl Cl CH.sub.3 Vin 1211. F CF.sub.3 Cl Cl CH.sub.3 Vin 1212. F OCH.sub.3 Cl Cl CH.sub.3 Vin 1213. F OCF.sub.3 Cl Cl CH.sub.3 Vin 1214. F CN Cl Cl CH.sub.3 Vin 1215. F H Cl Cl Et Vin 1216. F F Cl Cl Et Vin 1217. F Cl Cl Cl Et Vin 1218. F Br Cl Cl Et Vin 1219. F I Cl Cl Et Vin 1220. F CH.sub.3 Cl Cl Et Vin 1221. F Et Cl Cl Et Vin 1222. F CF.sub.3 Cl Cl Et Vin 1223. F OCH.sub.3 Cl Cl Et Vin 1224. F OCF.sub.3 Cl Cl Et Vin 1225. F CN Cl Cl Et Vin 1226. F Br Cl Br CH.sub.3 CH.sub.3 1227. F Br Cl Br CH.sub.3 Et 1228. F Br Cl Br Et Et 1229. F Br Cl Br CH.sub.3 Vin 1230. F Br Cl Br Et Vin 1231. F I Cl I CH.sub.3 CH.sub.3 1232. F I Cl I CH.sub.3 Et 1233. F I Cl I Et Et 1234. F I Cl I CH.sub.3 Vin 1235. F I Cl I Et Vin 1236. F H Cl CN CH.sub.3 CH.sub.3 1237. F F Cl CN CH.sub.3 CH.sub.3 1238. F Cl Cl CN CH.sub.3 CH.sub.3 1239. F Br Cl CN CH.sub.3 CH.sub.3 1240. F I Cl CN CH.sub.3 CH.sub.3 1241. F CH.sub.3 Cl CN CH.sub.3 CH.sub.3 1242. F Et Cl CN CH.sub.3 CH.sub.3 1243. F CF.sub.3 Cl CN CH.sub.3 CH.sub.3 1244. F OCH.sub.3 Cl CN CH.sub.3 CH.sub.3 1245. F OCF.sub.3 Cl CN CH.sub.3 CH.sub.3 1246. F CN Cl CN CH.sub.3 CH.sub.3 1247. F H Cl CN CH.sub.3 Et 1248. F F Cl CN CH.sub.3 Et 1249. F Cl Cl CN CH.sub.3 Et 1250. F Br Cl CN CH.sub.3 Et 1251. F I Cl CN CH.sub.3 Et 1252. F CH.sub.3 Cl CN CH.sub.3 Et 1253. F Et Cl CN CH.sub.3 Et 1254. F CF.sub.3 Cl CN CH.sub.3 Et 1255. F OCH.sub.3 Cl CN CH.sub.3 Et 1256. F OCF.sub.3 Cl CN CH.sub.3 Et 1257. F CN Cl CN CH.sub.3 Et 1258. F H Cl CN Et Et 1259. F F Cl CN Et Et 1260. F Cl Cl CN Et Et 1261. F Br Cl CN Et Et 1262. F I Cl CN Et Et 1263. F CH.sub.3 Cl CN Et Et 1264. F Et Cl CN Et Et 1265. F CF.sub.3 Cl CN Et Et 1266. F OCH.sub.3 Cl CN Et Et 1267. F OCF.sub.3 Cl CN Et Et 1268. F CN Cl CN Et Et 1269. F H Cl CN CH.sub.3 Vin 1270. F F Cl CN CH.sub.3 Vin 1271. F Cl Cl CN CH.sub.3 Vin 1272. F Br Cl CN CH.sub.3 Vin 1273. F I Cl CN CH.sub.3 Vin 1274. F CH.sub.3 Cl CN CH.sub.3 Vin 1275. F Et Cl CN CH.sub.3 Vin 1276. F CF.sub.3 Cl CN CH.sub.3 Vin 1277. F OCH.sub.3 Cl CN CH.sub.3 Vin 1278. F OCF.sub.3 Cl CN CH.sub.3 Vin 1279. F CN Cl CN CH.sub.3 Vin 1280. F H Cl CN Et Vin 1281. F F Cl CN Et Vin 1282. F Cl Cl CN Et Vin 1283. F Br Cl CN Et Vin 1284. F I Cl CN Et Vin 1285. F CH.sub.3 Cl CN Et Vin 1286. F Et Cl CN Et Vin 1287. F CF.sub.3 Cl CN Et Vin 1288. F OCH.sub.3 Cl CN Et Vin 1289. F OCF.sub.3 Cl CN Et Vin 1290. F CN Cl CN Et Vin 1291. Cl H H H CH.sub.3 CH.sub.3 1292. Cl F H H CH.sub.3 CH.sub.3 1293. Cl Cl H H CH.sub.3 CH.sub.3 1294. Cl Br H H CH.sub.3 CH.sub.3 1295. Cl I H H CH.sub.3 CH.sub.3 1296. Cl CH.sub.3 H H CH.sub.3 CH.sub.3 1297. Cl Et H H CH.sub.3 CH.sub.3 1298. Cl CF.sub.3 H H CH.sub.3 CH.sub.3 1299. Cl OCH.sub.3 H H CH.sub.3 CH.sub.3 1300. Cl OCF.sub.3 H H CH.sub.3 CH.sub.3 1301. Cl CN H H CH.sub.3 CH.sub.3 1302. Cl H H H CH.sub.3 Et 1303. Cl F H H CH.sub.3 Et 1304. Cl Cl H H CH.sub.3 Et 1305. Cl Br H H CH.sub.3 Et 1306. Cl I H H CH.sub.3 Et 1307. Cl CH.sub.3 H H CH.sub.3 Et 1308. Cl Et H H CH.sub.3 Et 1309. Cl CF.sub.3 H H CH.sub.3 Et 1310. Cl OCH.sub.3 H H CH.sub.3 Et 1311. Cl OCF.sub.3 H H CH.sub.3 Et 1312. Cl CN H H CH.sub.3 Et 1313. Cl H H H Et Et 1314. Cl F H H Et Et 1315. Cl Cl H H Et Et 1316. Cl Br H H Et Et 1317. Cl I H H Et Et 1318. Cl CH.sub.3 H H Et Et 1319. Cl Et H H Et Et 1320. Cl CF.sub.3 H H Et Et 1321. Cl OCH.sub.3 H H Et Et 1322. Cl OCF.sub.3 H H Et Et 1323. Cl CN H H Et Et 1324. Cl H H H CH.sub.3 Vin 1325. Cl F H H CH.sub.3 Vin 1326. Cl Cl H H CH.sub.3 Vin 1327. Cl Br H H CH.sub.3 Vin 1328. Cl I H H CH.sub.3 Vin 1329. Cl CH.sub.3 H H CH.sub.3 Vin 1330. Cl Et H H CH.sub.3 Vin 1331. Cl CF.sub.3 H H CH.sub.3 Vin 1332. Cl OCH.sub.3 H H CH.sub.3 Vin 1333. Cl OCF.sub.3 H H CH.sub.3 Vin 1334. Cl CN H H CH.sub.3 Vin 1335. Cl H H H Et Vin 1336. Cl F H H Et Vin 1337. Cl Cl H H Et Vin 1338. Cl Br H H Et Vin 1339. Cl I H H Et Vin 1340. Cl CH.sub.3 H H Et Vin 1341. Cl Et H H Et Vin 1342. Cl CF.sub.3 H H Et Vin 1343. Cl OCH.sub.3 H H Et Vin 1344. Cl OCF.sub.3 H H Et Vin 1345. Cl CN H H Et Vin 1346. Cl H H F CH.sub.3 CH.sub.3 1347. Cl F H F CH.sub.3 CH.sub.3 1348. Cl Cl H F CH.sub.3 CH.sub.3 1349. Cl Br H F CH.sub.3 CH.sub.3 1350. Cl I H F CH.sub.3 CH.sub.3 1351. Cl CH.sub.3 H F CH.sub.3 CH.sub.3 1352. Cl Et H F CH.sub.3 CH.sub.3 1353. Cl CF.sub.3 H F CH.sub.3 CH.sub.3 1354. Cl OCH.sub.3 H F CH.sub.3 CH.sub.3 1355. Cl OCF.sub.3 H F CH.sub.3 CH.sub.3 1356. Cl CN H F CH.sub.3 CH.sub.3 1357. Cl H H F CH.sub.3 Et 1358. Cl F H F CH.sub.3 Et 1359. Cl Cl H F CH.sub.3 Et 1360. Cl Br H F CH.sub.3 Et 1361. Cl I H F CH.sub.3 Et 1362. Cl CH.sub.3 H F CH.sub.3 Et 1363. Cl Et H F CH Et 1364. Cl CF.sub.3 H F CH.sub.3 Et 1365. Cl OCH.sub.3 H F CH.sub.3 Et 1366. Cl OCF.sub.3 H F CH.sub.3 Et 1367. Cl CN H F CH.sub.3 Et 1368. Cl H H F Et Et 1369. Cl F H F Et Et 1370. Cl Cl H F Et Et 1371. Cl Br H F Et Et 1372. Cl I H F Et Et 1373. Cl CH.sub.3 H F Et Et 1374. Cl Et H F Et Et 1375. Cl CF.sub.3 H F Et Et 1376. Cl OCH.sub.3 H F Et Et 1377. Cl OCF.sub.3 H F Et Et 1378. Cl CN H F Et Et 1379. Cl H H F CH.sub.3 Vin 1380. Cl F H F CH.sub.3 Vin 1381. Cl Cl H F CH.sub.3 Vin 1382. Cl Br H F CH.sub.3 Vin 1383. Cl I H F CH.sub.3 Vin 1384. Cl CH.sub.3 H F CH.sub.3 Vin 1385. Cl Et H F CH.sub.3 Vin 1386. Cl CF.sub.3 H F CH.sub.3 Vin 1387. Cl OCH.sub.3 H F CH.sub.3 Vin 1388. Cl OCF.sub.3 H F CH.sub.3 Vin 1389. Cl CN H F CH.sub.3 Vin 1390. Cl H H F Et Vin 1391. Cl F H F Et Vin 1392. Cl Cl H F Et Vin 1393. Cl Br H F Et Vin 1394. Cl I H F Et Vin 1395. Cl CH.sub.3 H F Et Vin 1396. Cl Et H F Et Vin 1397. Cl CF.sub.3 H F Et Vin 1398. Cl OCH.sub.3 H F Et Vin 1399. Cl OCF.sub.3 H F Et Vin 1400. Cl CN H F Et Vin 1401. Cl H H Cl CH.sub.3 CH.sub.3 1402. Cl F H Cl CH.sub.3 CH.sub.3 1403. Cl Cl H Cl CH.sub.3 CH.sub.3 1404. Cl Br H Cl CH.sub.3 CH.sub.3 1405. Cl I H Cl CH.sub.3 CH.sub.3 1406. Cl CH.sub.3 H Cl CH.sub.3 CH.sub.3 1407. Cl Et H Cl CH.sub.3 CH.sub.3 1408. Cl CF.sub.3 H Cl CH.sub.3 CH.sub.3 1409. Cl OCH.sub.3 H Cl CH.sub.3 CH.sub.3 1410. Cl OCF.sub.3 H Cl CH.sub.3 CH.sub.3 1411. Cl CN H Cl CH.sub.3 CH.sub.3 1412. Cl H H Cl CH.sub.3 Et 1413. Cl F H Cl CH.sub.3 Et 1414. Cl Cl H Cl CH.sub.3 Et 1415. Cl Br H Cl CH.sub.3 Et 1416. Cl I H Cl CH.sub.3 Et 1417. Cl CH.sub.3 H Cl CH.sub.3 Et 1418. Cl Et H Cl CH.sub.3 Et 1419. Cl CF.sub.3 H Cl CH.sub.3 Et 1420. Cl OCH.sub.3 H Cl CH.sub.3 Et 1421. Cl OCF.sub.3 H Cl CH.sub.3 Et 1422. Cl CN H Cl CH.sub.3 Et 1423. Cl H H Cl Et Et 1424. Cl F H Cl Et Et 1425. Cl Cl H Cl Et Et 1426. Cl Br H Cl Et Et 1427. Cl I H Cl Et Et 1428. Cl CH.sub.3 H Cl Et Et 1429. Cl Et H Cl Et Et 1430. Cl CF.sub.3 H Cl Et Et 1431. Cl OCH.sub.3 H Cl Et Et 1432. Cl OCF.sub.3 H Cl Et Et 1433. Cl CN H Cl Et Et 1434. Cl H H Cl CH.sub.3 Vin 1435. Cl F H Cl CH.sub.3 Vin 1436. Cl Cl H Cl CH.sub.3 Vin 1437. Cl Br H Cl CH.sub.3 Vin 1438. Cl I H Cl CH.sub.3 Vin 1439. Cl CH.sub.3 H Cl CH.sub.3 Vin 1440. Cl Et H Cl CH.sub.3 Vin 1441. Cl CF.sub.3 H Cl CH.sub.3 Vin 1442. Cl OCH.sub.3 H Cl CH.sub.3 Vin 1443. Cl OCF.sub.3 H Cl CH.sub.3 Vin 1444. Cl CN H Cl CH.sub.3 Vin 1445. Cl H H Cl Et Vin 1446. Cl F H Cl Et Vin 1447. Cl Cl H Cl Et Vin 1448. Cl Br H Cl Et Vin 1449. Cl I H Cl Et Vin 1450. Cl CH.sub.3 H Cl Et Vin 1451. Cl Et H Cl Et Vin 1452. Cl CF.sub.3 H Cl Et Vin 1453. Cl OCH.sub.3 H Cl Et Vin 1454. Cl OCF.sub.3 H Cl Et Vin 1455. Cl CN H Cl Et Vin 1456. Cl Br H Br CH.sub.3 CH.sub.3 1457. Cl Br H Br CH.sub.3 Et 1458. Cl Br H Br Et Et 1459. Cl Br H Br CH.sub.3 Vin 1460. Cl Br H Br Et Vin 1461. Cl I H I CH.sub.3 CH.sub.3 1462. Cl I H I CH.sub.3 Et 1463. Cl I H I Et Et 1464. Cl I H I CH.sub.3 Vin 1465. Cl I H I Et Vin 1466. Cl H H CN CH.sub.3 CH.sub.3 1467. Cl F H CN CH.sub.3 CH.sub.3 1468. Cl Cl H CN CH.sub.3 CH.sub.3 1469. Cl Br H CN CH.sub.3 CH.sub.3 1470. Cl I H CN CH.sub.3 CH.sub.3 1471. Cl CH.sub.3 H CN CH.sub.3 CH.sub.3 1472. Cl Et H CN CH.sub.3 CH.sub.3 1473. Cl CF.sub.3 H CN CH.sub.3 CH.sub.3 1474. Cl OCH.sub.3 H CN CH.sub.3 CH.sub.3 1475. Cl OCF.sub.3 H CN CH.sub.3 CH.sub.3 1476. Cl CN H CN CH.sub.3 CH.sub.3 1477. Cl H H CN CH.sub.3 Et 1478. Cl F H CN CH.sub.3 Et 1479. Cl Cl H CN CH.sub.3 Et 1480. Cl Br H CN CH.sub.3 Et 1481. Cl I H CN CH.sub.3 Et 1482. Cl CH.sub.3 H CN CH.sub.3 Et 1483. Cl Et H CN CH.sub.3 Et 1484. Cl CF.sub.3 H CN CH.sub.3 Et 1485. Cl OCH.sub.3 H CN CH.sub.3 Et 1486. Cl OCF.sub.3 H CN CH.sub.3 Et 1487. Cl CN H CN CH.sub.3 Et 1488. Cl H H CN Et Et 1489. Cl F H CN Et Et 1490. Cl Cl H CN Et Et 1491. Cl Br H CN Et Et 1492. Cl I H CN Et Et 1493. Cl CH.sub.3 H CN Et Et 1494. Cl Et H CN Et Et 1495. Cl CF.sub.3 H CN Et Et 1496. Cl OCH.sub.3 H CN Et Et 1497. Cl OCF.sub.3 H CN Et Et 1498. Cl CN H CN Et Et 1499. Cl H H CN CH.sub.3 Vin 1500. Cl F H CN CH.sub.3 Vin 1501. Cl Cl H CN CH.sub.3 Vin 1502. Cl Br H CN CH.sub.3 Vin 1503. Cl I H CN CH.sub.3 Vin 1504. Cl CH.sub.3 H CN CH.sub.3 Vin 1505. Cl Et H CN CH.sub.3 Vin 1506. Cl CF.sub.3 H CN CH.sub.3 Vin 1507. Cl OCH.sub.3 H CN CH.sub.3 Vin 1508. Cl OCF.sub.3 H CN CH.sub.3 Vin 1509. Cl CN H CN CH.sub.3 Vin 1510. Cl H H CN Et Vin 1511. Cl F H CN Et Vin 1512. Cl Cl H CN Et Vin 1513. Cl Br H CN Et Vin 1514. Cl I H CN Et Vin 1515. Cl CH.sub.3 H CN Et Vin 1516. Cl Et H CN Et Vin 1517. Cl CF.sub.3 H CN Et Vin 1518. Cl OCH.sub.3 H CN Et Vin 1519. Cl OCF.sub.3 H CN Et Vin 1520. Cl CN H CN Et Vin 1521. Cl H F H CH.sub.3 CH.sub.3 1522. Cl F F H CH.sub.3 CH.sub.3 1523. Cl Cl F H CH.sub.3 CH.sub.3 1524. Cl Br F H CH.sub.3 CH.sub.3 1525. Cl I F H CH.sub.3 CH.sub.3 1526. Cl CH.sub.3 F H CH.sub.3 CH.sub.3 1527. Cl Et F H CH.sub.3 CH.sub.3 1528. Cl CF.sub.3 F H CH.sub.3 CH.sub.3 1529. Cl OCH.sub.3 F H CH.sub.3 CH.sub.3 1530. Cl OCF.sub.3 F H CH.sub.3 CH.sub.3 1531. Cl CN F H CH.sub.3 CH.sub.3 1532. Cl H F H CH.sub.3 Et 1533. Cl F F H CH.sub.3 Et 1534. Cl Cl F H CH.sub.3 Et 1535. Cl Br F H CH.sub.3 Et 1536. Cl I F H CH.sub.3 Et 1537. Cl CH.sub.3 F H CH.sub.3 Et 1538. Cl Et F H CH.sub.3 Et 1539. Cl CF.sub.3 F H CH.sub.3 Et 1540. Cl OCH.sub.3 F H CH.sub.3 Et 1541. Cl OCF.sub.3 F H CH.sub.3 Et 1542. Cl CN F H CH.sub.3 Et 1543. Cl H F H Et Et 1544. Cl F F H Et Et 1545. Cl Cl F H Et Et 1546. Cl Br F H Et Et 1547. Cl I F H Et Et 1548. Cl CH.sub.3 F H Et Et 1549. Cl Et F H Et Et 1550. Cl CF F H Et Et 1551. Cl OCH.sub.3 F H Et Et 1552. Cl OCF.sub.3 F H Et Et 1553. Cl CN F H Et Et 1554. Cl H F H CH.sub.3 Vin 1555. Cl F F H CH.sub.3 Vin 1556. Cl Cl F H CH.sub.3 Vin 1557. Cl Br F H CH.sub.3 Vin 1558. Cl I F H CH.sub.3 Vin 1559. Cl CH.sub.3 F H CH.sub.3 Vin 1560. Cl Et F H CH.sub.3 Vin 1561. Cl CF F H CH.sub.3 Vin 1562. Cl OCH.sub.3 F H CH.sub.3 Vin 1563. Cl OCF.sub.3 F H CH.sub.3 Vin 1564. Cl CN F H CH.sub.3 Vin 1565. Cl H F H Et Vin 1566. Cl F F H Et Vin 1567. Cl Cl F H Et Vin 1568. Cl Br F H Et Vin 1569. Cl I F H Et Vin 1570. Cl CH.sub.3 F H Et Vin 1571. Cl Et F H Et Vin 1572. Cl CF.sub.3 F H Et Vin 1573. Cl OCH.sub.3 F H Et Vin 1574. Cl OCF.sub.3 F H Et Vin 1575. Cl CN F H Et Vin 1576. Cl H F F CH.sub.3 CH.sub.3 1577. Cl F F F CH.sub.3 CH.sub.3 1578. Cl Cl F F CH.sub.3 CH.sub.3 1579. Cl Br F F CH.sub.3 CH.sub.3 1580. Cl I F F CH.sub.3 CH.sub.3 1581. Cl CH.sub.3 F F CH.sub.3 CH.sub.3 1582. Cl Et F F CH.sub.3 CH.sub.3 1583. Cl CF.sub.3 F F CH.sub.3 CH.sub.3 1584. Cl OCH.sub.3 F F CH.sub.3 CH.sub.3 1585. Cl OCF.sub.3 F F CH.sub.3 CH.sub.3 1586. Cl CN F F CH.sub.3 CH.sub.3 1587. Cl H F F CH.sub.3 Et 1588. Cl F F F CH.sub.3 Et 1589. Cl Cl F F CH.sub.3 Et 1590. Cl Br F F CH.sub.3 Et 1591. Cl I F F CH.sub.3 Et 1592. Cl CH.sub.3 F F CH.sub.3 Et 1593. Cl Et F F CH.sub.3 Et 1594. Cl CF.sub.3 F F CH.sub.3 Et 1595. Cl OCH.sub.3 F F CH.sub.3 Et 1596. Cl OCF.sub.3 F F CH.sub.3 Et 1597. Cl CN F F CH.sub.3 Et 1598. Cl H F F Et Et 1599. Cl F F F Et Et 1600. Cl Cl F F Et Et 1601. Cl Br F F Et Et 1602. Cl I F F Et Et 1603. Cl CH.sub.3 F F Et Et 1604. Cl Et F F Et Et 1605. Cl CF.sub.3 F F Et Et 1606. Cl OCH.sub.3 F F Et Et 1607. Cl OCF.sub.3 F F Et Et 1608. Cl CN F F Et Et 1609. Cl H F F CH.sub.3 Vin 1610. Cl F F F CH.sub.3 Vin 1611. Cl Cl F F CH.sub.3 Vin 1612. Cl Br F F CH.sub.3 Vin 1613. Cl I F F CH.sub.3 Vin 1614. Cl CH.sub.3 F F CH.sub.3 Vin 1615. Cl Et F F CH.sub.3 Vin 1616. Cl CF.sub.3 F F CH.sub.3 Vin 1617. Cl OCH.sub.3 F F CH.sub.3 Vin 1618. Cl OCF.sub.3 F F CH.sub.3 Vin 1619. Cl CN F F CH.sub.3 Vin 1620. Cl H F F Et Vin 1621. Cl F F F Et Vin 1622. Cl Cl F F Et Vin 1623. Cl Br F F Et Vin 1624. Cl I F F Et Vin 1625. Cl CH.sub.3 F F Et Vin 1626. Cl Et F F Et Vin 1627. Cl CF.sub.3 F F Et Vin 1628. Cl OCH.sub.3 F F Et Vin 1629. Cl OCF.sub.3 F F Et Vin 1630. Cl CN F F Et Vin 1631. Cl H F Cl CH.sub.3 CH.sub.3 1632. Cl F F Cl CH.sub.3 CH.sub.3 1633. Cl Cl F Cl CH.sub.3 CH.sub.3 1634. Cl Br F Cl CH.sub.3 CH.sub.3 1635. Cl I F Cl CH.sub.3 CH.sub.3 1636. Cl CH.sub.3 F Cl CH.sub.3 CH.sub.3 1637. Cl Et F Cl CH.sub.3 CH.sub.3 1638. Cl CF.sub.3 F Cl CH.sub.3 CH.sub.3 1639. Cl OCH.sub.3 F Cl CH.sub.3 CH.sub.3 1640. Cl OCF.sub.3 F Cl CH.sub.3 CH.sub.3 1641. Cl CN F Cl CH.sub.3 CH.sub.3 1642. Cl H F Cl CH.sub.3 Et 1643. Cl F F Cl CH.sub.3 Et 1644. Cl Cl F Cl CH.sub.3 Et 1645. Cl Br F Cl CH.sub.3 Et 1646. Cl I F Cl CH.sub.3 Et 1647. Cl CH.sub.3 F Cl CH.sub.3 Et 1648. Cl Et F Cl CH.sub.3 Et 1649. Cl CF.sub.3 F Cl CH.sub.3 Et 1650. Cl OCH.sub.3 F Cl CH.sub.3 Et 1651. Cl OCF.sub.3 F Cl CH.sub.3 Et 1652. Cl CN F Cl CH.sub.3 Et 1653. Cl H F Cl Et Et 1654. Cl F F Cl Et Et 1655. Cl Cl F Cl Et Et 1656. Cl Br F Cl Et Et 1657. Cl I F Cl Et Et 1658. Cl CH F Cl Et Et 1659. Cl Et F Cl Et Et 1660. Cl CF.sub.3 F Cl Et Et 1661. Cl OCH.sub.3 F Cl Et Et 1662. Cl OCF.sub.3 F Cl Et Et 1663. Cl CN F Cl Et Et 1664. Cl H F Cl CH.sub.3 Vin 1665. Cl F F Cl CH.sub.3 Vin 1666. Cl Cl F Cl CH.sub.3 Vin 1667. Cl Br F Cl CH.sub.3 Vin 1668. Cl I F Cl CH.sub.3 Vin 1669. Cl CH.sub.3 F Cl CH.sub.3 Vin 1670. Cl Et F Cl CH.sub.3 Vin 1671. Cl CF.sub.3 F Cl CH.sub.3 Vin 1672. Cl OCH.sub.3 F Cl CH.sub.3 Vin 1673. Cl OCF.sub.3 F Cl CH.sub.3 Vin 1674. Cl CN F Cl CH.sub.3 Vin 1675. Cl H F Cl Et Vin 1676. Cl F F Cl Et Vin 1677. Cl Cl F Cl Et Vin 1678. Cl Br F Cl Et Vin 1679. Cl I F Cl Et Vin 1680. Cl CH.sub.3 F Cl Et Vin 1681. Cl Et F Cl Et Vin 1682. Cl CF.sub.3 F Cl Et Vin 1683. Cl OCH.sub.3 F Cl Et Vin 1684. Cl OCF.sub.3 F Cl Et Vin 1685. Cl CN F Cl Et Vin 1686. Cl Br F Br CH.sub.3 CH.sub.3 1687. Cl Br F Br CH.sub.3 Et 1688. Cl Br F Br Et Et 1689. Cl Br F Br CH.sub.3 Vin 1690. Cl Br F Br Et Vin 1691. Cl I F I CH.sub.3 CH.sub.3 1692. Cl I F I CH.sub.3 Et 1693. Cl I F I Et Et 1694. Cl I F I CH.sub.3 Vin 1695. Cl I F I Et Vin 1696. Cl H F CN CH.sub.3 CH.sub.3 1697. Cl F F CN CH.sub.3 CH.sub.3 1698. Cl Cl F CN CH.sub.3 CH.sub.3 1699. Cl Br F CN CH.sub.3 CH.sub.3 1700. Cl I F CN CH.sub.3 CH.sub.3 1701. Cl CH.sub.3 F CN CH.sub.3 CH.sub.3 1702. Cl Et F CN CH.sub.3 CH.sub.3 1703. Cl CF.sub.3 F CN CH.sub.3 CH.sub.3 1704. Cl OCH.sub.3 F CN CH.sub.3 CH.sub.3 1705. Cl OCF.sub.3 F CN CH.sub.3 CH.sub.3 1706. Cl CN F CN CH.sub.3 CH.sub.3 1707. Cl H F CN CH.sub.3 Et 1708. Cl F F CN CH.sub.3 Et 1709. Cl Cl F CN CH.sub.3 Et 1710. Cl Br F CN CH.sub.3 Et 1711. Cl I F CN CH.sub.3 Et 1712. Cl CH.sub.3 F CN CH.sub.3 Et 1713. Cl Et F CN CH.sub.3 Et 1714. Cl CF.sub.3 F CN CH.sub.3 Et 1715. Cl OCH.sub.3 F CN CH.sub.3 Et 1716. Cl OCF.sub.3 F CN CH.sub.3 Et 1717. Cl CN F CN CH.sub.3 Et 1718. Cl H F CN Et Et 1719. Cl F F CN Et Et 1720. Cl Cl F CN Et Et 1721. Cl Br F CN Et Et 1722. Cl I F CN Et Et 1723. Cl CH.sub.3 F CN Et Et 1724. Cl Et F CN Et Et 1725. Cl CF.sub.3 F CN Et Et 1726. Cl OCH.sub.3 F CN Et Et 1727. Cl OCF.sub.3 F CN Et Et 1728. Cl CN F CN Et Et 1729. Cl H F CN CH.sub.3 Vin 1730. Cl F F CN CH.sub.3 Vin 1731. Cl Cl F CN CH.sub.3 Vin 1732. Cl Br F CN CH.sub.3 Vin 1733. Cl I F CN CH.sub.3 Vin 1734. Cl CH.sub.3 F CN CH.sub.3 Vin 1735. Cl Et F CN CH.sub.3 Vin 1736. Cl CF.sub.3 F CN CH.sub.3 Vin 1737. Cl OCH.sub.3 F CN CH.sub.3 Vin 1738. Cl OCF.sub.3 F CN CH.sub.3 Vin 1739. Cl CN F CN CH.sub.3 Vin 1740. Cl H F CN Et Vin 1741. Cl F F CN Et Vin 1742. Cl Cl F CN Et Vin 1743. Cl Br F CN Et Vin 1744. Cl I F CN Et Vin 1745. Cl CH.sub.3 F CN Et Vin 1746. Cl Et F CN Et Vin 1747. Cl CF.sub.3 F CN Et Vin 1748. Cl OCH.sub.3 F CN Et Vin 1749. Cl OCF.sub.3 F CN Et Vin 1750. Cl CN F CN Et Vin 1751. Cl H Cl H CH.sub.3 CH.sub.3 1752. Cl F Cl H CH.sub.3 CH.sub.3 1753. Cl Cl Cl H CH.sub.3 CH.sub.3 1754. Cl Br Cl H CH.sub.3 CH.sub.3 1755. Cl I Cl H CH.sub.3 CH.sub.3 1756. Cl CH.sub.3 Cl H CH.sub.3 CH.sub.3 1757. Cl Et Cl H CH.sub.3 CH.sub.3 1758. Cl CF.sub.3 Cl H CH.sub.3 CH.sub.3 1759. Cl OCH.sub.3 Cl H CH.sub.3 CH.sub.3 1760. Cl OCF.sub.3 Cl H CH.sub.3 CH.sub.3 1761. Cl CN Cl H CH.sub.3 CH.sub.3 1762. Cl H Cl H CH.sub.3 Et 1763. Cl F Cl H CH.sub.3 Et 1764. Cl Cl Cl H CH.sub.3 Et 1765. Cl Br Cl H CH.sub.3 Et 1766. Cl I Cl H CH.sub.3 Et 1767. Cl CH.sub.3 Cl H CH.sub.3 Et 1768. Cl Et Cl H CH.sub.3 Et 1769. Cl CF.sub.3 Cl H CH.sub.3 Et 1770. Cl OCH.sub.3 Cl H CH.sub.3 Et 1771. Cl OCF.sub.3 Cl H CH.sub.3 Et 1772. Cl CN Cl H CH.sub.3 Et 1773. Cl H Cl H Et Et 1774. Cl F Cl H Et Et 1775. Cl Cl Cl H Et Et 1776. Cl Br Cl H Et Et 1777. Cl I Cl H Et Et 1778. Cl CH.sub.3 Cl H Et Et 1779. Cl Et Cl H Et Et 1780. Cl CF.sub.3 Cl H Et Et 1781. Cl OCH.sub.3 Cl H Et Et 1782. Cl OCF.sub.3 Cl H Et Et 1783. Cl CN Cl H Et Et 1784. Cl H Cl H CH.sub.3 Vin 1785. Cl F Cl H CH.sub.3 Vin 1786. Cl Cl Cl H CH.sub.3 Vin 1787. Cl Br Cl H CH.sub.3 Vin 1788. Cl I Cl H CH.sub.3 Vin 1789. Cl CH.sub.3 Cl H CH.sub.3 Vin 1790. Cl Et Cl H CH.sub.3 Vin 1791. Cl CF.sub.3 Cl H CH.sub.3 Vin 1792. Cl OCH.sub.3 Cl H CH.sub.3 Vin 1793. Cl OCF.sub.3 Cl H CH.sub.3 Vin 1794. Cl CN Cl H CH.sub.3 Vin 1795. Cl H Cl H Et Vin 1796. Cl F Cl H Et Vin 1797. Cl Cl Cl H Et Vin 1798. Cl Br Cl H Et Vin 1799. Cl I Cl H Et Vin 1800. Cl CH.sub.3 Cl H Et Vin 1801. Cl Et Cl H Et Vin 1802. Cl CF.sub.3 Cl H Et Vin 1803. Cl OCH.sub.3 Cl H Et Vin 1804. Cl OCF.sub.3 Cl H Et Vin 1805. Cl CN Cl H Et Vin 1806. Cl H Cl F CH.sub.3 CH.sub.3 1807. Cl F Cl F CH.sub.3 CH.sub.3 1808. Cl Cl Cl F CH.sub.3 CH.sub.3 1809. Cl Br Cl F CH.sub.3 CH.sub.3 1810. Cl I Cl F CH.sub.3 CH.sub.3 1811. Cl CH.sub.3 Cl F CH.sub.3 CH.sub.3 1812. Cl Et Cl F CH.sub.3 CH.sub.3 1813. Cl CF.sub.3 Cl F CH.sub.3 CH.sub.3 1814. Cl OCH.sub.3 Cl F CH.sub.3 CH.sub.3 1815. Cl OCF.sub.3 Cl F CH.sub.3 CH.sub.3 1816. Cl CN Cl F CH.sub.3 CH.sub.3 1817. Cl H Cl F CH.sub.3 Et 1818. Cl F Cl F CH.sub.3 Et 1819. Cl Cl Cl F CH.sub.3 Et 1820. Cl Br Cl F CH.sub.3 Et 1821. Cl I Cl F CH.sub.3 Et 1822. Cl CH.sub.3 Cl F CH.sub.3 Et 1823. Cl Et Cl F CH.sub.3 Et 1824. Cl CF.sub.3 Cl F CH.sub.3 Et 1825. Cl OCH.sub.3 Cl F CH.sub.3 Et 1826. Cl OCF.sub.3 Cl F CH.sub.3 Et 1827. Cl CN Cl F CH.sub.3 Et 1828. Cl H Cl F Et Et 1829. Cl F Cl F Et Et 1830. Cl Cl Cl F Et Et 1831. Cl Br Cl F Et Et 1832. Cl I Cl F Et Et 1833. Cl CH.sub.3 Cl F Et Et 1834. Cl Et Cl F Et Et 1835. Cl CF.sub.3 Cl F Et Et 1836. Cl OCH.sub.3 Cl F Et Et 1837. Cl OCF.sub.3 Cl F Et Et 1838. Cl CN Cl F Et Et 1839. Cl H Cl F CH.sub.3 Vin 1840. Cl F Cl F CH.sub.3 Vin 1841. Cl Cl Cl F CH.sub.3 Vin 1842. Cl Br Cl F CH.sub.3 Vin 1843. Cl I Cl F CH.sub.3 Vin 1844. Cl CH.sub.3 Cl F CH.sub.3 Vin 1845. Cl Et Cl F CH.sub.3 Vin 1846. Cl CF.sub.3 Cl F CH.sub.3 Vin 1847. Cl OCH.sub.3 Cl F CH.sub.3 Vin 1848. Cl OCF.sub.3 Cl F CH.sub.3 Vin 1849. Cl CN Cl F CH.sub.3 Vin 1850. Cl H Cl F Et Vin 1851. Cl F Cl F Et Vin 1852. Cl Cl Cl F Et Vin 1853. Cl Br Cl F Et Vin 1854. Cl I Cl F Et Vin 1855. Cl CH.sub.3 Cl F Et Vin 1856. Cl Et Cl F Et Vin 1857. Cl CF.sub.3 Cl F Et Vin 1858. Cl OCH.sub.3 Cl F Et Vin 1859. Cl OCF.sub.3 Cl F Et Vin 1860. Cl CN Cl F Et Vin 1861. Cl H Cl Cl CH.sub.3 CH.sub.3 1862. Cl F Cl Cl CH.sub.3 CH.sub.3 1863. Cl Cl Cl Cl CH.sub.3 CH.sub.3 1864. Cl Br Cl Cl CH.sub.3 CH.sub.3 1865. Cl I Cl Cl CH.sub.3 CH.sub.3 1866. Cl CH.sub.3 Cl Cl CH.sub.3 CH.sub.3 1867. Cl Et Cl Cl CH.sub.3 CH.sub.3 1868. Cl CF.sub.3 Cl Cl CH.sub.3 CH.sub.3 1869. Cl OCH.sub.3 Cl Cl CH.sub.3 CH.sub.3 1870. Cl OCF.sub.3 Cl Cl CH.sub.3 CH.sub.3 1871. Cl CN Cl Cl CH.sub.3 CH.sub.3 1872. Cl H Cl Cl CH.sub.3 Et 1873. Cl F Cl Cl CH.sub.3 Et 1874. Cl Cl Cl Cl CH.sub.3 Et 1875. Cl Br Cl Cl CH.sub.3 Et 1876. Cl I Cl Cl CH.sub.3 Et 1877. Cl CH.sub.3 Cl Cl CH.sub.3 Et 1878. Cl Et Cl Cl CH.sub.3 Et 1879. Cl CF.sub.3 Cl Cl CH.sub.3 Et 1880. Cl OCH.sub.3 Cl Cl CH.sub.3 Et 1881. Cl OCF.sub.3 Cl Cl CH.sub.3 Et 1882. Cl CN Cl Cl CH.sub.3 Et 1883. Cl H Cl Cl Et Et 1884. Cl F Cl Cl Et Et 1885. Cl Cl Cl Cl Et Et 1886. Cl Br Cl Cl Et Et 1887. Cl I Cl Cl Et Et 1888. Cl CH.sub.3 Cl Cl Et Et 1889. Cl Et Cl Cl Et Et 1890. Cl CF.sub.3 Cl Cl Et Et 1891. Cl OCH.sub.3 Cl Cl Et Et 1892. Cl OCF.sub.3 Cl Cl Et Et 1893. Cl CN Cl Cl Et Et 1894. Cl H Cl Cl CH.sub.3 Vin 1895. Cl F Cl Cl CH.sub.3 Vin 1896. Cl Cl Cl Cl CH.sub.3 Vin 1897. Cl Br Cl Cl CH.sub.3 Vin 1898. Cl I Cl Cl CH.sub.3 Vin 1899. Cl CH.sub.3 Cl Cl CH.sub.3 Vin 1900. Cl Et Cl Cl CH.sub.3 Vin 1901. Cl CF.sub.3 Cl Cl CH.sub.3 Vin 1902. Cl OCH.sub.3 Cl Cl CH.sub.3 Vin 1903. Cl OCF.sub.3 Cl Cl CH.sub.3 Vin 1904. Cl CN Cl Cl CH.sub.3 Vin 1905. Cl H Cl Cl Et Vin 1906. Cl F Cl Cl Et Vin 1907. Cl Cl Cl Cl Et Vin 1908. Cl Br Cl Cl Et Vin 1909. Cl I Cl Cl Et Vin 1910. Cl CH.sub.3 Cl Cl Et Vin 1911. Cl Et Cl Cl Et Vin 1912. Cl CF.sub.3 Cl Cl Et Vin 1913. Cl OCH.sub.3 Cl Cl Et Vin 1914. Cl OCF.sub.3 Cl Cl Et Vin 1915. Cl CN Cl Cl Et Vin 1916. Cl Br Cl Br CH.sub.3 CH.sub.3 1917. Cl Br Cl Br CH.sub.3 Et 1918. Cl Br Cl Br Et Et 1919. Cl Br Cl Br CH.sub.3 Vin 1920. Cl Br Cl Br Et Vin 1921. Cl I Cl I CH.sub.3 CH.sub.3 1922. Cl I Cl I CH.sub.3 Et 1923. Cl I Cl I Et Et 1924. Cl I Cl I CH.sub.3 Vin 1925. Cl I Cl I Et Vin 1926. Cl H Cl CN CH.sub.3 CH.sub.3 1927. Cl F Cl CN CH.sub.3 CH.sub.3 1928. Cl Cl Cl CN CH.sub.3 CH.sub.3 1929. Cl Br Cl CN CH.sub.3 CH.sub.3 1930. Cl I Cl CN CH.sub.3 CH.sub.3 1931. Cl CH.sub.3 Cl CN CH.sub.3 CH.sub.3 1932. Cl Et Cl CN CH.sub.3 CH.sub.3 1933. Cl CF.sub.3 Cl CN CH.sub.3 CH.sub.3 1934. Cl OCH.sub.3 Cl CN CH.sub.3 CH.sub.3 1935. Cl OCF.sub.3 Cl CN CH.sub.3 CH.sub.3 1936. Cl CN Cl CN CH.sub.3 CH.sub.3 1937. Cl H Cl CN CH.sub.3 Et 1938. Cl F Cl CN CH.sub.3 Et 1939. Cl Cl Cl CN CH.sub.3 Et 1940. Cl Br Cl CN CH.sub.3 Et 1941. Cl I Cl CN CH.sub.3 Et 1942. Cl CH.sub.3 Cl CN CH.sub.3 Et 1943. Cl Et Cl CN CH.sub.3 Et 1944. Cl CF.sub.3 Cl CN CH.sub.3 Et 1945. Cl OCH.sub.3 Cl CN CH.sub.3 Et 1946. Cl OCF.sub.3 Cl CN CH.sub.3 Et 1947. Cl CN Cl CN CH.sub.3 Et 1948. Cl H Cl CN Et Et 1949. Cl F Cl CN Et Et 1950. Cl Cl Cl CN Et Et 1951. Cl Br Cl CN Et Et 1952. Cl I Cl CN Et Et 1953. Cl CH.sub.3 Cl CN Et Et 1954. Cl Et Cl CN Et Et 1955. Cl CF.sub.3 Cl CN Et Et 1956. Cl OCH.sub.3 Cl CN Et Et 1957. Cl OCF.sub.3 Cl CN Et Et 1958. Cl CN Cl CN Et Et 1959. Cl H Cl CN CH.sub.3 Vin 1960. Cl F Cl CN CH.sub.3 Vin 1961. Cl Cl Cl CN CH.sub.3 Vin 1962. Cl Br Cl CN CH.sub.3 Vin 1963. Cl I Cl CN CH.sub.3 Vin 1964. Cl CH.sub.3 Cl CN CH.sub.3 Vin 1965. Cl Et Cl CN CH.sub.3 Vin 1966. Cl CF.sub.3 Cl CN CH.sub.3 Vin 1967. Cl OCH.sub.3 Cl CN CH.sub.3 Vin 1968. Cl OCF.sub.3 Cl CN CH.sub.3 Vin 1969. Cl CN Cl CN CH.sub.3 Vin 1970. Cl H Cl CN Et Vin 1971. Cl F Cl CN Et Vin 1972. Cl Cl Cl CN Et Vin 1973. Cl Br Cl CN Et Vin 1974. Cl I Cl CN Et Vin 1975. Cl CH.sub.3 Cl CN Et Vin 1976. Cl Et Cl CN Et Vin 1977. Cl CF.sub.3 Cl CN Et Vin 1978. Cl OCH.sub.3 Cl CN Et Vin 1979. Cl OCF.sub.3 Cl CN Et Vin 1980. Cl CN Cl CN Et Vin 1981. H H H H CH.sub.3 nPr 1982. H F H H CH.sub.3 nPr 1983. H Cl H H CH.sub.3 nPr 1984. H Br H H CH.sub.3 nPr 1985. H I H H CH.sub.3 nPr 1986. H CH.sub.3 H H CH.sub.3 nPr 1987. H Et H H CH.sub.3 nPr 1988. H CF.sub.3 H H CH.sub.3 nPr 1989. H OCH.sub.3 H H CH.sub.3 nPr 1990. H OCF.sub.3 H H CH.sub.3 nPr 1991. H CN H H CH.sub.3 nPr 1992. H H H F CH.sub.3 nPr 1993. H F H F CH.sub.3 nPr 1994. H Cl H F CH.sub.3 nPr 1995. H Br H F CH.sub.3 nPr 1996. H I H F CH.sub.3 nPr 1997. H CH.sub.3 H F CH.sub.3 nPr 1998. H Et H F CH.sub.3 nPr 1999. H CF.sub.3 H F CH.sub.3 nPr 2000. H OCH.sub.3 H F CH.sub.3 nPr 2001. H OCF.sub.3 H F CH.sub.3 nPr 2002. H CN H F CH.sub.3 nPr 2003. H H H Cl CH.sub.3 nPr 2004. H F H Cl CH.sub.3 nPr 2005. H Cl H Cl CH.sub.3 nPr 2006. H Br H Cl CH.sub.3 nPr 2007. H I H Cl CH.sub.3 nPr 2008. H CH.sub.3 H Cl CH.sub.3 nPr 2009. H Et H Cl CH.sub.3 nPr 2010. H CF.sub.3 H Cl CH.sub.3 nPr 2011. H OCH.sub.3 H Cl CH.sub.3 nPr 2012. H OCF.sub.3 H Cl CH.sub.3 nPr 2013. H CN H Cl CH.sub.3 nPr 2014. H H H H CH.sub.3 iPr 2015. H F H H CH.sub.3 iPr 2016. H Cl H H CH.sub.3 iPr 2017. H Br H H CH.sub.3 iPr 2018. H I H H CH.sub.3 iPr 2019. H CH.sub.3 H H CH.sub.3 iPr 2020. H Et H H CH.sub.3 iPr 2021. H CF.sub.3 H H CH.sub.3 iPr 2022. H OCH.sub.3 H H CH.sub.3 iPr 2023. H OCF.sub.3 H H CH.sub.3 iPr 2024. H CN H H CH.sub.3 iPr 2025. H H H F CH.sub.3 iPr 2026. H F H F CH.sub.3 iPr 2027. H Cl H F CH.sub.3 iPr 2028. H Br H F CH.sub.3 iPr 2029. H I H F CH.sub.3 iPr 2030. H CH.sub.3 H F CH.sub.3 iPr 2031. H Et H F CH.sub.3 iPr 2032. H CF.sub.3 H F CH.sub.3 iPr 2033. H OCH.sub.3 H F CH.sub.3 iPr 2034. H OCF.sub.3 H F CH.sub.3 iPr 2035. H CN H F CH.sub.3 iPr 2036. H H H Cl CH.sub.3 iPr 2037. H F H Cl CH.sub.3 iPr 2038. H Cl H Cl CH.sub.3 iPr 2039. H Br H Cl CH.sub.3 iPr 2040. H I H Cl CH.sub.3 iPr 2041. H CH.sub.3 H Cl CH.sub.3 iPr 2042. H Et H Cl CH.sub.3 iPr 2043. H CF.sub.3 H Cl CH.sub.3 iPr 2044. H OCH.sub.3 H Cl CH.sub.3 iPr 2045. H OCF.sub.3 H Cl CH.sub.3 iPr 2046. H CN H Cl CH.sub.3 iPr Et ethyl Vin vinyl (CHCH.sub.2) nPr n-propyl iPr isopropyl
[0564] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2C(O)OH.
[0565] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2C(O)OCH.sub.3.
[0566] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2C(O)OCH.sub.2CH.sub.3.
[0567] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2C(O)OCH.sub.2CH.sub.2CH.sub.3.
[0568] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2C(O)OCH(CH.sub.3) 2.
[0569] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2C(O)OCH.sub.2CH.sub.2CH.sub.2CH.sub.3.
[0570] Particularly preferred are moreover compounds (1) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2C(O)OCH(CH.sub.3) CH.sub.2CH.sub.3.
[0571] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2C(O)OCH.sub.2CH(CH.sub.3) 2.
[0572] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2C(O)OC(CH.sub.3) 3.
[0573] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2C(O)OCH.sub.2CN.
[0574] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2C(O)OCH.sub.2CHF.sub.2.
[0575] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2C(O)OCH.sub.2CH.sub.2F.
[0576] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2C(O)OCH.sub.2CF.sub.3.
[0577] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2C(O)OCH.sub.2CHCH.sub.2.
[0578] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2C(O)OCH.sub.2CCH.
[0579] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2C(O)OCH.sub.2C.sub.6H.sub.5 (CH.sub.2C.sub.6H.sub.5=benzyl).
[0580] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2C(O)O-cyclopropyl.
[0581] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2C(O)O-cyclobutyl.
[0582] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2C(O)O-cyclopentyl.
[0583] Particularly preferred are moreover compounds (1) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2C(O)O-cyclohexyl.
[0584] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2CH.sub.2C(O)OH.
[0585] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2CH.sub.2C(O)OCH.sub.3.
[0586] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2CH.sub.2C(O)OCH.sub.2CH.sub.3.
[0587] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2CH.sub.2C(O)OCH.sub.2CH.sub.2CH.sub.3.
[0588] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2CH.sub.2C(O)OCH(CH.sub.3) 2.
[0589] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2CH.sub.2C(O)OCH.sub.2CH.sub.2CH.sub.2CH.sub.3.
[0590] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2CH.sub.2C(O)OCH(CH.sub.3) CH.sub.2CH.sub.3.
[0591] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2CH.sub.2C(O)OCH.sub.2CH(CH.sub.3) 2.
[0592] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2CH.sub.2C(O)OC(CH.sub.3) 3.
[0593] Particularly preferred are moreover compounds (1) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2CH.sub.2C(O)OCH.sub.2CN.
[0594] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2CH.sub.2C(O)OCH.sub.2CHF.sub.2.
[0595] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2CH.sub.2C(O)OCH.sub.2CH.sub.2F.
[0596] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2CH.sub.2C(O)OCH.sub.2CF.sub.3.
[0597] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2CH.sub.2C(O)OCH.sub.2CHCH.sub.2.
[0598] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2CH.sub.2C(O)OCH.sub.2CCH.
[0599] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2CH.sub.2C(O)OCH.sub.2C.sub.6H.sub.5 (CH.sub.2C.sub.6H.sub.5=benzyl).
[0600] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2CH.sub.2C(O)O-cyclopropyl.
[0601] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2CH.sub.2C(O)O-cyclobutyl.
[0602] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2CH.sub.2C(O)O-cyclopentyl.
[0603] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2CH.sub.2C(O)O-cyclohexyl.
[0604] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2C(O) NHCH.sub.3.
[0605] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2C(O) NHCH.sub.2CH.sub.3.
[0606] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2C(O) NHOCH.sub.3.
[0607] Particularly preferred are moreover compounds (1) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2C(O) NHOCH.sub.2CH.sub.3.
[0608] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2C(O) NHS(O)CH.sub.3.
[0609] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2C(O) NHS(O)CH.sub.2CH.sub.3.
[0610] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2C(O) NHS(O)CF.sub.3.
[0611] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2C(O) NHS(O)CH.sub.2CH.sub.2F.
[0612] Particularly preferred are moreover compounds (1) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2C(O) NHS(O)CH.sub.2CHF.sub.2.
[0613] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2C(O) NHS(O)CH.sub.2CF.sub.3.
[0614] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2C(O) NHS(O).sub.2CH.sub.3.
[0615] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2C(O) NHS(O).sub.2CH.sub.2CH.sub.3.
[0616] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2C(O) NHS(O).sub.2CH.sub.2CH.sub.2CH.sub.3.
[0617] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2C(O) NHS(O).sub.2CH(CH.sub.3) 2.
[0618] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2C(O) NHS(O).sub.2CH.sub.2CH.sub.2CH.sub.2CH.sub.3.
[0619] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2C(O) NHS(O).sub.2CH(CH.sub.3) CH.sub.2CH.sub.3.
[0620] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2C(O) NHS(O).sub.2CH.sub.2CH(CH.sub.3) 2.
[0621] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2C(O) NHS(O).sub.2C(CH.sub.3) 3.
[0622] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2C(O) NHS(O).sub.2CF.sub.3.
[0623] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2C(O) NHS(O).sub.2CH.sub.2CHF.sub.2.
[0624] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2C(O) NHS(O).sub.2CH.sub.2CH.sub.2F.
[0625] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2C(O) NHS(O).sub.2CH.sub.2CF.sub.3.
[0626] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2C(O) NHS(O).sub.2N(H) CH.sub.3.
[0627] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2C(O) NHS(O).sub.2N(H) CH.sub.2CH.sub.3.
[0628] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2C(O) NHS(O).sub.2N(H) CH.sub.2CH.sub.2CH.sub.3.
[0629] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2C(O) NHS(O).sub.2N(H) CH(CH.sub.3) 2.
[0630] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2C(O) NHS(O).sub.2N(H) CH.sub.2CH.sub.2CH.sub.2CH.sub.3.
[0631] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2C(O) NHS(O).sub.2N(H) CH(CH.sub.3) CH.sub.2CH.sub.3.
[0632] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2C(O) NHS(O).sub.2N(H) CH.sub.2CH(CH.sub.3) 2.
[0633] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2C(O) NHS(O).sub.2N(H) C(CH.sub.3) 2.
[0634] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2C(O) NHS(O).sub.2N(CH.sub.3) 2.
[0635] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2C(O) NHS(O).sub.2N(CH.sub.3) CH.sub.2CH.sub.3.
[0636] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2C(O) NHS(O).sub.2N(CH.sub.3) CH.sub.2CH.sub.2CH.sub.3.
[0637] Particularly preferred are moreover compounds (1) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2C(O) NHS(O).sub.2N(CH.sub.3) CH(CH.sub.3) 2.
[0638] Particularly preferred are moreover compounds (1) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2C(O) NHS(O).sub.2N(CH.sub.3) CH.sub.2CH.sub.2CH.sub.2CH.sub.3.
[0639] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2C(O) NHS(O).sub.2N(CH.sub.3) CH(CH.sub.3) CH.sub.2CH.sub.3.
[0640] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2C(O) NHS(O).sub.2N(CH.sub.3) CH.sub.2CH(CH.sub.3) 2.
[0641] Particularly preferred are moreover compounds (1) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2C(O) NHS(O).sub.2N(CH.sub.3) C(CH.sub.3) 2.
[0642] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2C(O) NHS(O).sub.2-piperdin-1-yl.
[0643] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2C(O) NHS(O).sub.2-piperazin-1-yl.
[0644] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2C(O) NHS(O).sub.2-morpholin-4-yl.
[0645] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for CH(CH.sub.3)CH.sub.2C(O) NHS(O).sub.2-thiomorpholin-4-yl.
[0646] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.1), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O) OH.
[0647] Particularly preferred are moreover compounds (1) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.1), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.3.
[0648] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.1), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.2CH.sub.3.
[0649] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.2), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O) OH.
[0650] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.2), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.3.
[0651] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.2), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.2CH.sub.3.
[0652] Particularly preferred are moreover compounds (1) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.3), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O) OH.
[0653] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.3), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.3.
[0654] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.3), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.2CH.sub.3.
[0655] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.4), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O) OH.
[0656] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.4), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.3.
[0657] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.4), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.2CH.sub.3.
[0658] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.5), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O) OH.
[0659] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.5), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.3.
[0660] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.5), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.2CH.sub.3.
[0661] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.6), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O) OH.
[0662] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.6), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.3.
[0663] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.6), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.2CH.sub.3.
[0664] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.7), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O) OH.
[0665] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.7), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.3.
[0666] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.7), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.2CH.sub.3.
[0667] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.8), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O) OH.
[0668] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.8), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.3.
[0669] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.8), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.2CH.sub.3.
[0670] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.9), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O) OH.
[0671] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.9), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.3.
[0672] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.9), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.2CH.sub.3.
[0673] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.10), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O) OH.
[0674] Particularly preferred are moreover compounds (1) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.10), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.3.
[0675] Particularly preferred are moreover compounds (1) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.10), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.2CH.sub.3.
[0676] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.11), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O) OH.
[0677] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.11), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.3.
[0678] Particularly preferred are moreover compounds (1) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.11), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.2CH.sub.3.
[0679] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.12), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O) OH.
[0680] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.12), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.3.
[0681] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.12), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.2CH.sub.3.
[0682] Particularly preferred are moreover compounds (1) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.13), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O) OH.
[0683] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.13), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.3.
[0684] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.13), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.2CH.sub.3.
[0685] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.14), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O) OH.
[0686] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.14), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.3.
[0687] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.14), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.2CH.sub.3.
[0688] Particularly preferred are moreover compounds (1) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.15), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O) OH.
[0689] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.15), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.3.
[0690] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.15), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.2CH.sub.3.
[0691] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.16), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O) OH.
[0692] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.16), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.3.
[0693] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.16), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.2CH.sub.3.
[0694] Particularly preferred are moreover compounds (1) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.17), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O) OH.
[0695] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.17), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.3.
[0696] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.17), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.2CH.sub.3.
[0697] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.18), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O) OH.
[0698] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.18), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.3.
[0699] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.18), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.2CH.sub.3.
[0700] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.19), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O) OH.
[0701] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.19), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.3.
[0702] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.19), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.2CH.sub.3.
[0703] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.20), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O) OH.
[0704] Particularly preferred are moreover compounds (1) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.20), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.3.
[0705] Particularly preferred are moreover compounds (1) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.20), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.2CH.sub.3.
[0706] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.21), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O) OH.
[0707] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.21), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.3.
[0708] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.21), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.2CH.sub.3.
[0709] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.22), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O) OH.
[0710] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.22), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.3.
[0711] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.22), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.2CH.sub.3.
[0712] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.23), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O) OH.
[0713] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.23), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.3.
[0714] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.23), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.2CH.sub.3.
[0715] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.24), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O) OH.
[0716] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.24), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.3.
[0717] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.24), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.2CH.sub.3.
[0718] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.25), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O) OH.
[0719] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.25), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.3.
[0720] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.25), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.2CH.sub.3.
[0721] Particularly preferred are moreover compounds (1) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.26), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O) OH.
[0722] Particularly preferred are moreover compounds (1) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.26), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.3.
[0723] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.26), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.2CH.sub.3.
[0724] Particularly preferred are moreover compounds (1) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.27), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O) OH.
[0725] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.27), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.3.
[0726] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.27), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.2CH.sub.3.
[0727] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.28), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O) OH.
[0728] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.28), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.3.
[0729] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.28), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.2CH.sub.3.
[0730] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.29), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O) OH.
[0731] Particularly preferred are moreover compounds (1) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.29), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.3.
[0732] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.29), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.2CH.sub.3.
[0733] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.30), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O) OH.
[0734] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.30), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.3.
[0735] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.30), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.2CH.sub.3.
[0736] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.31), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O) OH.
[0737] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.31), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.3.
[0738] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.31), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.2CH.sub.3.
[0739] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.32), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O) OH.
[0740] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.32), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.3.
[0741] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.32), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.2CH.sub.3.
[0742] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.33), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O) OH.
[0743] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.33), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.3.
[0744] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.33), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.2CH.sub.3.
[0745] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.34), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O) OH.
[0746] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.34), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.3.
[0747] Particularly preferred are moreover compounds (1) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.34), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.2CH.sub.3.
[0748] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.35), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O) OH.
[0749] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.35), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.3.
[0750] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.35), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.2CH.sub.3.
[0751] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.36), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O) OH.
[0752] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.36), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is-C(O)OCH.sub.3.
[0753] Particularly preferred are moreover compounds (I) in which for a single compound R.sup.1, R.sup.6 and R.sup.9 are hydrogen, R.sup.2, R.sup.3, R.sup.4, R.sup.6, R.sup.7 and R.sup.8 have one of the meanings as defined in a single line of table A and X-Y in combination stand for a ring of the formula (Z.sup.3%), wherein # denotes the attachment point to the remainder of the molecule and R.sup.x is C(O)OCH.sub.2CH.sub.3.
##STR00015## ##STR00016## ##STR00017## ##STR00018## ##STR00019##
[0754] Among rings Z.sup.1 to Z.sup.36, particular preference is given to rings Z.sup.9.
[0755] The compounds of formula (I) according to the invention can be prepared by standard processes of organic chemistry, for example by the following processes:
##STR00020##
[0756] The compounds of formula (I) can be prepared according to methods or in analogy to methods that are described in the prior art. The synthesis takes advantage of starting materials that are commercially available or may be prepared according to conventional procedures starting from readily available compounds.
[0757] Compounds of the formula (I) can be prepared from the carboxylic acids (III) and commercially available amines (II) using an organic base and a coupling reagent. Thus, compounds of formula (I) can be synthesized from the corresponding carboxylic acids (1 eq.) using a coupling reagent (1-2 eq.), for example T.sub.3P (propane phosphonic acid anhydride) or HATU (O-(7-azabenzotriazole-1-yl)-N,N,N,N-tetramethyluronium-hexafluorophosphate), an organic base (1-3 eq.) and the amines (II) (1-3 eq.). The reaction is typically carried out in an organic solvent. Preferably an aprotic organic solvent is used. Most preferably tetrahydrofuran (THF), N,N-dimethylformamide (DMF) or acetonitrile (ACN) are used. The reaction is carried out at temperatures between 0 C. and reflux. Preferably the reaction is carried out at room temperature. Preferably the organic base is triethylamine or N,N-diisopropylethylamine.
##STR00021##
[0758] The carboxylic acids (III) are commercially available or can be prepared from the corresponding esters (IV) (wherein RP is alkyl or benzyl). If RP is alkyl, esters (IV) may be cleaved using aqueous alkali metal hydroxides. Preferably lithium hydroxide, sodium hydroxide or potassium hydroxide (1-2 eq.) are employed. The reaction is typically carried out in mixtures of water and an organic solvent. Preferably the organic solvent is THF, methanol or acetonitrile. The reaction is carried out at temperatures between 0 C. and 100 C. Preferably the reaction is carried at room temperature. If RP is benzyl in (IV), then the ester may be cleaved using palladium on charcoal (0.001-1 eq.) as catalyst and hydrogen gas at temperatures between 0 C. and reflux. Preferably the reaction is carried out at room temperature. Typically, an organic solvent is employed. Preferably THF, methanol or ethanol are employed.
[0759] Compounds of the formula (IV) are commercially available or can be prepared by known methods. For example, the esters (IV) can be prepared according to methods described in Organometallics 2001, 20 (22), 4675-4682. For example, they can be prepared from the carboxylic acids (VI) and commercially available amines (V) using a base and a coupling reagent.
##STR00022##
[0760] Thus, compounds of formula (IV) can be synthesized from the corresponding carboxylic acids (1 eq.) using a coupling reagent (1-2 eq.), for example T.sub.3P (propanephosphonic acid anhydride) or HATU (O-(7-azabenzotriazole-1-yl)-N,N,N,N-tetramethyluronium-hexafluorphosphate), an organic base (1-3 eq.) and the amines (V) (1-3 eq.). The reaction is typically carried out in an organic solvent. Preferably an aprotic organic solvent is used. Most preferably tetrahydrofuran (THF), N,Ndimethylformamide (DMF) or acetonitrile (ACN) are used. The reaction is carried out at temperatures between 0 C. to refluxing temperatures. Preferably the reaction is carried out at room temperature. Preferably the organic base is triethylamine or N,N-diisopropylethylamine.
##STR00023##
[0761] Carboxylic acid (VI) may be prepared from the corresponding diester by selective cleavage of one ester group. If R.sup.a is an alkyl ester, selective ester cleavage may be achieved using an aqueous base. Preferably an alkali metal hydroxide is used. Most preferably lithium hydroxide, sodium hydroxide or potassium hydroxide are used. The reaction is typically carried out in mixtures of water and an organic solvent. Preferably THF, methanol or acetonitrile are employed. The reaction is carried out at temperatures between 0 C. and 100 C., preferably at room temperature.
[0762] Alternatively, trimethyltin hydroxide (e.g. 1 eq.) in 1,2-dichlorethane at room temperature to reflux may be used (as described in Angew. Chem. Int. Ed, 2005, 44:1378-1382), preferably at reflux. If R.sup.a is benzyl in (VII), then the ester may be cleaved using palladium on charcoal (0.001-1 eq.) as catalyst and hydrogen gas at temperatures between 0 C. and reflux. Preferably the reaction is carried out at room temperature. Typically, an organic solvent is employed. Preferably THF, methanol or ethanol are employed.
[0763] The diesters (VII) are either commercially available or can be prepared by standard methods of organic chemistry.
##STR00024##
[0764] Amines of the formula (XIII) can be prepared from the lactames (XIV), which are either commercially available or may be prepared by alkylation as described in Org. Process Res. Dev. 2018, 22, 337-343, and commercially available alcohols (XV) using thionyl chloride (2 eq.) as described in Tetrahedron Lett. 2001, 42, 1347-1350. The reaction is typically carried out in the coupling alcohols (XV) as the solvent. The reaction is carried out at temperatures between 0 C. to refluxing temperatures. Preferably the reaction is carried out at room temperature.
[0765] To widen the spectrum of action, the compounds of formula (I) may be mixed with many representatives of other herbicidal or growth-regulating active ingredient groups and then applied concomitantly. Suitable components for combinations are, for example, herbicides from the classes of the acetamides, amides, aryloxyphenoxypropionates, benzamides, benzofuran, benzoic acids, benzothiadiazinones, bipyridylium, carbamates, chloroacetamides, chlorocarboxylic acids, cyclohexanediones, dinitroanilines, dinitrophenol, diphenyl ether, glycines, imidazolinones, isoxazoles, isoxazolidinones, nitriles, N-phenylphthalimides, oxadiazoles, oxazolidinediones, oxyacetamides, phenoxycarboxylic acids, phenylcarbamates, phenylpyrazoles, phenylpyrazolines, phenylpyridazines, phosphinic acids, phosphoroamidates, phosphorodithioates, phthalamates, pyrazoles, pyridazinones, pyridines, pyridinecarboxylic acids, pyridinecarboxamides, pyrimidinediones, pyrimidinyl (thio)benzoates, quinolinecarboxylic acids, semicarbazones, sulfonylaminocarbonyltriazolinones, sulfonylureas, tetrazolinones, thiadiazoles, thiocarbamates, triazines, triazinones, triazoles, triazolinones, triazolocarboxamides, triazolopyrimidines, triketones, uracils, ureas.
[0766] It may furthermore be beneficial to apply the compounds of formula (I) alone or in combination with other herbicides, or else in the form of a mixture with other crop protection agents, for example together with agents for controlling pests or phytopathogenic fungi or bacteria. Also of interest is the miscibility with mineral salt solutions, which are employed for treating nutritional and trace element deficiencies. Other additives such as non-phytotoxic oils and oil concentrates may also be added.
[0767] In one embodiment of the present invention the combinations according to the present invention comprise at least one compound of formula (I) (compound A or component A) and at least one further active compound selected from herbicides B (compound B), preferably herbicides B of class b1) to b15), and safeners C(compound C).
[0768] In another embodiment of the present invention the combinations according to the present invention comprise at least one compound of formula (I) and at least one further active compound B (herbicide B).
[0769] Examples of herbicides B which can be used in combination with the compounds A of formula (I) according to the present invention are:
[0770] b1) from the group of the lipid biosynthesis inhibitors:
[0771] ACC-herbicides such as alloxydim, alloxydim-sodium, butroxydim, clethodim, clodinafop, clodinafop-propargyl, cycloxydim, cyhalofop, cyhalofop-butyl, diclofop, diclofop-methyl, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop, fluazifop-butyl, fluazifop-P, fluazifop-P-butyl, haloxyfop, haloxyfop-methyl, haloxyfop-P, haloxyfop-P-methyl, metamifop, pinoxaden, profoxydim, propaquizafop, quizalofop, quizalofop-ethyl, quizalofop-tefuryl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, sethoxydim, tepraloxydim, tralkoxydim, 4-(4-Chloro-4-cyclopropyl-2-fluoro [1,1-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3 (6H)-one (CAS 1312337-72-6); 4-(2,4-Dichloro-4-cyclopropyl [1,1-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3 (6H)-one (CAS 1312337-45-3); 4-(4-Chloro-4-ethyl-2-fluoro [1,1-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3 (6H)-one (CAS 1033757-93-5); 4-(2,4-Dichloro-4-ethyl [1,1-biphenyl]-3-yl)-2,2,6,6-tetramethyl-2Hpyran-3,5 (4H,6H)-dione (CAS 1312340-84-3); 5-(Acetyloxy)-4-(4-chloro-4-cyclopropyl-2-fluoro [1,1-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1312337-48-6); 5-(Acetyloxy)-4-(2,4-dichloro-4-cyclopropyl-[1,1-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one; 5-(Acetyloxy)-4-(4-chloro-4-ethyl-2-fluoro [1,1-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1312340-82-1); 5-(Acetyloxy)-4-(2,4-dichloro-4-ethyl [1,1-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1033760-55-2); 4-(4-Chloro-4-cyclopropyl-2-fluoro [1,1-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (CAS 1312337-51-1); 4-(2,4-Dichloro-4-cyclopropyl-[1,1-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester; 4-(4-Chloro-4-ethyl-2-fluoro [1,1-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (CAS 1312340-83-2); 4-(2,4-Dichloro-4-ethyl [1,1-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (CAS 1033760-58-5); and non ACC herbicides such as benfuresate, butylate, cycloate, dalapon, dimepiperate, EPTC, esprocarb, ethofumesate, flupropanate, molinate, orbencarb, pebulate, prosulfocarb, TCA, thiobencarb, tiocarbazil, triallate and vernolate;
[0772] b2) from the group of the ALS inhibitors:
[0773] sulfonylureas such as amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl, chlorimuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, flupyrsulfuron-methyl-sodium, foramsulfuron, halosulfuron, halosulfuron-methyl, imazosulfuron, iodosulfuron, iodosulfuron-methylsodium, iofensulfuron, iofensulfuron-sodium, mesosulfuron, metazosulfuron, metsulfuron, metsulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron, primisulfuron, primisulfuron-methyl, propyrisulfuron, prosulfuron, pyrazosulfuron, pyrazosulfuron-ethyl, rimsulfuron, sulfometuron, sulfometuron-methyl, sulfosulfuron, thifensulfuron, thifensulfuron-methyl, triasulfuron, tribenuron, tribenuron-methyl, trifloxysulfuron, triflusulfuron, triflusulfuron-methyl and tritosulfuron, imidazolinones such as imazamethabenz, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin and imazethapyr, triazolopyrimidine herbicides and sulfonanilides such as cloransulam, cloransulam-methyl, diclosulam, flumetsulam, florasulam, metosulam, penoxsulam, pyrimisulfan and pyroxsulam, pyrimidinylbenzoates such as bispyribac, bispyribac-sodium, pyribenzoxim, pyriftalid, pyriminobac, pyriminobac-methyl, pyrithiobac, pyrithiobac-sodium, 4-[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]-benzoic acid-1-methylethyl ester (CAS 420138-41-6), 4-[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]-benzoic acid propyl ester (CAS 420138-40-5), N-(4-bromophenyl)-2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzenemethanamine (CAS 420138 Jan. 8), sulfonylaminocarbonyl-triazolinone herbicides such as flucarbazone, flucarbazonesodium, propoxycarbazone, propoxycarbazone-sodium, thiencarbazone and thiencarbazone-methyl; and triafamone;
[0774] among these, a preferred embodiment of the invention relates to those compositions comprising at least one imidazolinone herbicide;
[0775] b3) from the group of the photosynthesis inhibitors:
[0776] amicarbazone, inhibitors of the photosystem II, e.g. 1-(6-tert-butylpyrimidin-4-yl)-2-hydroxy-4-methoxy-3-methyl-2H-pyrrol-5-one (CAS 1654744-66-7), 1-(5-tertbutylisoxazol-3-yl)-2-hydroxy-4-methoxy-3-methyl-2H-pyrrol-5-one (CAS 1637455 Dec. 9), 1-(5-tert-butylisoxazol-3-yl)-4-chloro-2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS 1637453-94-1), 1-(5-tert-butyl-1-methyl-pyrazol-3-yl)-4-chloro-2-hydroxy-3-methyl-2Hpyrrol-5-one (CAS 1654057-29-0), 1-(5-tert-butyl-1-methyl-pyrazol-3-yl)-3-chloro-2-hydroxy-4-methyl-2H-pyrrol-5-one (CAS 1654747-80-4), 4-hydroxy-1-methoxy-5-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one; (CAS 2023785-78-4), 4-hydroxy-1,5-dimethyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one (CAS 2023785-79-5), 5-ethoxy-4-hydroxy-1-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one (CAS 1701416-69-4), 4-hydroxy-1-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one (CAS 1708087-22-2), 4-hydroxy-1,5-dimethyl-3-[1-methyl-5-(trifluoromethyl) pyrazol-3-yl]imidazolidin-2-one (CAS 2023785-80-8), 1-(5-tertbutylisoxazol-3-yl)-4-ethoxy-5-hydroxy-3-methyl-imidazolidin-2-one (CAS 1844836-64-1), triazine herbicides, including of chlorotriazine, triazinones, triazindiones, methylthiotriazines and pyridazinones such as ametryn, atrazine, chloridazone, cyanazine, desmetryn, dimethametryn,hexazinone, metribuzin, prometon, prometryn, propazine, simazine, simetryn, terbumeton, terbuthylazin, terbutryn and trietazin, aryl urea such as chlorobromuron, chlorotoluron, chloroxuron, dimefuron, diuron, fluometuron, isoproturon, isouron, linuron, metamitron, methabenzthiazuron, metobenzuron, metoxuron, monolinuron, neburon, siduron, tebuthiuron and thiadiazuron, phenyl carbamates such as desmedipham, karbutilat, phenmedipham, phenmedipham-ethyl, nitrile herbicides such as bromofenoxim, bromoxynil and its salts and esters, ioxynil and its salts and esters, uraciles such as bromacil, lenacil and terbacil, and bentazon and bentazon-sodium, pyridate, pyridafol, pentanochlor and propanil and inhibitors of the photosystem I such as diquat, diquat-dibromide, paraquat, paraquat-dichloride and paraquat-dimetilsulfate. Among these, a preferred embodiment of the invention relates to those compositions comprising at least one aryl urea herbicide. Among these, likewise a preferred embodiment of the invention relates to those compositions comprising at least one triazine herbicide. Among these, likewise a preferred embodiment of the invention relates to those compositions comprising at least one nitrile herbicide;
[0777] b4) from the group of the protoporphyrinogen-IX oxidase inhibitors:
[0778] acifluorfen, acifluorfen-sodium, azafenidin, bencarbazone, benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, chlomethoxyfen, chlorphthalim, cinidon-ethyl, cyclopyranil, fluazolate, flufenpyr, flufenpyr-ethyl, flumiclorac, flumicloracpentyl, flumioxazin, fluoroglycofen, fluoroglycofen-ethyl, fluthiacet, fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazol, pyraclonil, pyraflufen, pyraflufen-ethyl, saflufenacil, sulfentrazone, thidiazimin, tiafenacil, trifludimoxazin, ethyl [3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl) phenoxy]-2-pyridyloxy]acetate (CAS 353292-31-6; S-3100), N-ethyl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 452098-92-9), N-tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 915396-43-9), N-ethyl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 452099 May 7), N-tetrahydrofurfuryl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 452100 Mar. 7), 3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl]-1,5-dimethyl-6-thioxo-[1,3,5]triazinan-2,4-dione (CAS 451484-50-7), 2-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-4,5,6,7-tetrahydro-isoindole-1,3-dione (CAS 1300118-96-0), 1-methyl-6-trifluoromethyl-3-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-1H-pyrimidine-2,4-dione (CAS 1304113-05-0), methyl (E)-4-[2-chloro-5-[4-chloro-5-(difluoromethoxy)-1 H-methyl-pyrazol-3-yl]-4-fluorophenoxy]-3-methoxy-but-2-enoate (CAS 948893-00-3), and 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)-1H-pyrimidine-2,4-dione (CAS 212754 Feb. 4), 2-[2-chloro-5-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]-4-fluorophenoxy]-2-methoxy-acetic acid methyl ester (CAS 1970221-16-9), 2-[2-[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1 (2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]phenoxy]-acetic acid methyl ester (CAS 2158274-96-3), 2-[2-[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1 (2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]phenoxy]acetic acid ethyl ester (CAS 158274-50-9), methyl 2-[3-[2-chloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-1,2,4-triazol-1-yl]-4-fluoro-phenoxy]-2 -pyridyl]oxy]acetate (CAS 2271389-22-9), ethyl 2-[3-[2-chloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-1,2,4-triazol-1-yl]-4-fluoro-phenoxy]-2-pyridyl]oxy]acetate (CAS 2230679-62-4), 2-[3-[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1 (2H)pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]-2-pyridinyl]oxy]-acetic acid methyl ester (CAS 2158275-73-9), 2-[3-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1 (2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]-2-pyridinyl]oxy]acetic acid ethyl ester (CAS 2158274-56-5), 2-[2-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1 (2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]phenoxy]-N-(methylsulfonyl)-acetamide (CAS 2158274-53-2), 2-[[3-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1 (2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]-2-pyridinyl]oxy]-N-(methylsulfonyl)-acetamide (CAS 2158276-22-1);
[0779] b5) from the group of the bleacher herbicides:
[0780] PDS inhibitors: beflubutamid, diflufenican, fluridone, flurochloridone, flurtamone, norflurazon, picolinafen, and 4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)-pyrimidine (CAS 180608-33-7), HPPD inhibitors: benzobicyclon, benzofenap, bicyclopyrone, clomazone, fenquinotrione, isoxaflutole, mesotrione, oxotrione (CAS 1486617-21-3), pyrasulfotole, pyrazolynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, tolpyralate, topramezone, bleacher, unknown target: aclonifen, amitrole flumeturon 2-chloro-3-methylsulfanyl-N-(1-methyltetrazol-5-yl)-4-(trifluoromethyl) benzamide (CAS 1361139-71-0), bixlozone and 2-(2,5-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone (CAS 81778-66-7);
[0781] b6) from the group of the EPSP synthase inhibitors:
[0782] glyphosate, glyphosate-isopropylammonium, glyposate-potassium and glyphosatetrimesium (sulfosate);
[0783] b7) from the group of the glutamine synthase inhibitors:
[0784] bilanaphos (bialaphos), bilanaphos-sodium, glufosinate, glufosinate-P and glufosinateammonium;
[0785] b8) from the group of the DHP synthase inhibitors:
[0786] asulam;
[0787] b9) from the group of the mitosis inhibitors:
[0788] compounds of group K1: dinitroanilines such as benfluralin, butralin, dinitramine, ethalfluralin, fluchloralin, oryzalin, pendimethalin, prodiamine and trifluralin, phosphoramidates such as amiprophos, amiprophos-methyl, and butamiphos, benzoic acid herbicides such as chlorthal, chlorthal-dimethyl, pyridines such as dithiopyr and thiazopyr, benzamides such as propyzamide and tebutam; compounds of group K2: carbetamide, chlorpropham, flamprop, flamprop-isopropyl, flamprop-methyl, flampropM-isopropyl, flamprop-M-methyl and propham; among these, compounds of group K1, in particular dinitroanilines are preferred;
[0789] b10) from the group of the VLCFA inhibitors:
[0790] chloroacetamides such as acetochlor, alachlor, amidochlor, butachlor, dimethachlor, dimethenamid, dimethenamid-P, metazachlor, metolachlor, metolachlor-S, pethoxamid, pretilachlor, propachlor, propisochlor and thenylchlor, oxyacetanilides such as flufenacet and mefenacet, acetanilides such as diphenamid, naproanilide, napropamide and napropamide-M, tetrazolinones such fentrazamide, and other herbicides such as anilofos, cafenstrole, fenoxasulfone, ipfencarbazone, piperophos, pyroxasulfone and isoxazoline compounds of the formulae II.1, 11.2, 11.3, 11.4, 11.5, 11.6, 11.7, 11.8 and II.9
##STR00025## ##STR00026## [0791] the isoxazoline compounds of the formula (II) are known in the art, e.g. from WO 2006/024820, WO 2006/037945, WO 2007/071900 and WO 2007/096576; [0792] among the VLCFA inhibitors, preference is given to chloroacetamides and oxyacetamides;
[0793] b11) from the group of the cellulose biosynthesis inhibitors:
[0794] chlorthiamid, dichlobenil, flupoxam, indaziflam, isoxaben, triaziflam and 1-cyclohexyl-5-pentafluorphenyloxy-14-[1,2,4,6]thiatriazin-3-ylamine (CAS 175899 Jan. 1);
[0795] b12) from the group of the decoupler herbicides:
[0796] dinoseb, dinoterb and DNOC and its salts;
[0797] b13) from the group of the auxinic herbicides:
[0798] 2,4-D and its salts and esters such as clacyfos, 2,4-DB and its salts and esters, aminocyclopyrachlor and its salts and esters, aminopyralid and its salts such as aminopyralid-dimethylammonium, aminopyralid-tris(2-hydroxypropyl) ammonium and its esters, benazolin, benazolin-ethyl, chloramben and its salts and esters, clomeprop, clopyralid and its salts and esters, dicamba and its salts and esters, dichlorprop and its salts and esters, dichlorprop-P and its salts and esters, flopyrauxifen, fluroxypyr, fluroxypyr-butometyl, fluroxypyr-meptyl, halauxifen and its salts and esters (CAS 943832-60-8); MCPA and its salts and esters, MCPA-thioethyl, MCPB and its salts and esters, mecoprop and its salts and esters, mecoprop-P and its salts and esters, picloram and its salts and esters, quinclorac, quinmerac, TBA (2,3,6) and its salts and esters, triclopyr and its salts and esters, florpyrauxifen, florpyrauxifen-benzyl (CAS 1390661-72-9) and 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl) picolinic acid (CAS 1629965-65-6);
[0799] b14) from the group of the auxin transport inhibitors: diflufenzopyr, diflufenzopyrsodium, naptalam and naptalam-sodium;
[0800] b15) from the group of the other herbicides: bromobutide, chlorflurenol, chlorflurenolmethyl, cinmethylin, cumyluron, cyclopyrimorate (CAS 499223-49-3) and its salts and esters, dalapon, dazomet, difenzoquat, difenzoquat-metilsulfate, dimethipin, DSMA, dymron, endothal and its salts, etobenzanid, flurenol, flurenol-butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan, maleic hydrazide, mefluidide, metam, methiozolin, methyl azide, methyl bromide, methyl-dymron, methyl iodide, MSMA, oleic acid, oxaziclomefone, pelargonic acid, pyributicarb, quinoclamine tetflupyrolimet, and tridiphane.
[0801] Moreover, it may be useful to apply the compounds of formula (I) in combination with safeners. Safeners are chemical compounds which prevent or reduce damage on useful plants without having a major impact on the herbicidal action of the compounds of the formula (I) towards undesired vegetation. They can be applied either before sowings (e.g. on seed treatments, shoots or seedlings) or in the pre-emergence application or post-emergence application of the useful plant. The safeners and the compounds of formula (I) and optionally the herbicides B can be applied simultaneously or in succession.
[0802] In another embodiment of the present invention the combinations according to the present invention comprise at least one compound of formula (I) and at least one safener C(component C).
[0803] Examples of safeners are e.g. (quinolin-8-oxy) acetic acids, 1-phenyl-5-haloalkyl-1H-1,2,4-triazol-3-carboxylic acids, 1-phenyl-4,5-dihydro-5-alkyl-1H-pyrazol-3,5-dicarboxylic acids, 4,5-dihydro-5,5-diaryl-3-isoxazol carboxylic acids, dichloroacetamides, alpha-oximinophenylacetonitriles, acetophenonoximes, 4,6-dihalo-2-phenylpyrimidines, N-[4-(aminocarbonyl)phenyl]sulfonyl]-2-benzoic amides, 1,8-naphthalic anhydride, 2-halo-4-(haloalkyl)-5-thiazol carboxylic acids, phosphorthiolates and N-alkyl-O-phenylcarbamates and their agriculturally acceptable salts and their agriculturally acceptable derivatives such amides, esters, and thioesters, provided they have an acid group.
[0804] Examples of safener compounds C are benoxacor, cloquintocet, cyometrinil, cyprosulfamide, dichlormid, dicyclonon, dietholate, fenchlorazole, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen, mefenpyr, mephenate, naphthalic anhydride, oxabetrinil, 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (MON4660, CAS 71526 Jul. 3), 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (R-29148, CAS 52836-31-4), metcamifen and BPCMS (CAS 54091 Jun. 4).
[0805] The active compounds B of groups b1) to b15) and the active compounds C are known herbicides and safeners, see, for example, The Compendium of Pesticide Common Names (http://www.alanwood.net/pesticides/); Farm Chemicals Handbook 2000 volume 86, Meister Publishing Company, 2000; B. Hock, C. Fedtke, R. R. Schmidt, Herbizide [Herbicides], Georg Thieme Verlag, Stuttgart 1995; W. H. Ahrens, Herbicide Handbook, 7th edition, Weed Science Society of America, 1994; and K. K. Hatzios, Herbicide Handbook, Supplement for the 7th edition, Weed Science Society of America, 1998. 2,2,5-Trimethyl-3-(dichloroacetyl)-1,3-oxazolidine [CAS No. 52836-31-4] is also referred to as R-29148. 4-(Dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane [CAS No. 71526 Jul. 3] is also referred to as AD-67 and MON 4660.
[0806] The assignment of the active compounds to the respective mechanisms of action is based on current knowledge. If several mechanisms of action apply to one active compound, this substance was only assigned to one mechanism of action.
[0807] The invention also relates to formulations comprising at least an auxiliary and at least one compound of formula (I) according to the invention.
[0808] A formulation comprises a pesticidally effective amount of a compound of formula (I). The term effective amount denotes an amount of the combination or of the compound of formula (I), which is sufficient for controlling undesired vegetation, especially for controlling undesired vegetation in crops (i.e. cultivated plants) and which does not result in a substantial damage to the treated crop plants. Such an amount can vary in a broad range and is dependent on various factors, such as the undesired vegetation to be controlled, the treated crop plants or material, the climatic conditions and the specific compound of formula (I) used.
[0809] The compounds of formula (I), their salts, amides, esters or thioesters can be converted into customary types of formulations, e.g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof. Examples for formulation types are suspensions (e.g. SC, OD, FS), emulsifiable concentrates (e.g. EC), emulsions (e.g. EW, EO, ES, ME), capsules (e.g. CS, ZC), pastes, pastilles, wettable powders or dusts (e.g. WP, SP, WS, DP, DS), pressings (e.g. BR, TB, DT), granules (e.g. WG, SG, GR, FG, GG, MG), insecticidal articles (e.g. LN), as well as gel formulations for the treatment of plant propagation materials such as seeds (e.g. GF). These and further formulation types are defined in the Catalogue of pesticide formulation types and international coding system, Technical Monograph No. 2,6th Ed. May 2008, CropLife International.
[0810] The formulations are prepared in a known manner, such as described by Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005.
[0811] Suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetting agents, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, anti-freezing agents, anti-foaming agents, colorants, tackifiers and binders.
[0812] Suitable solvents and liquid carriers are water and organic solvents, such as mineral oil fractions of medium to high boiling point, e.g. kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e.g. toluene, paraffin, tetrahydronaphthalene, alkylated naphthalenes; alcohols, e.g. ethanol, propanol, butanol, benzylalcohol, cyclohexanol; glycols; DMSO; ketones, e.g. cyclohexanone; esters, e.g. lactates, carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, e.g. N-methylpyrrolidone, fatty acid dimethylamides; and mixtures thereof.
[0813] Suitable solid carriers or fillers are mineral earths, e.g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharides, e.g. cellulose, starch; fertilizers, e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, e.g. cereal meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof.
[0814] Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emulsifier, dispersant, solubilizer, wetter, penetration enhancer, protective colloid, or adjuvant. Examples of surfactants are listed in Mccutcheon's, Vol. 1: Emulsifiers & Detergents, Mccutcheon's Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).
[0815] Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof. Examples of sulfonates are alkylarylsulfonates, diphenylsulfonates, alpha-olefin sulfonates, lignine sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyland tridecylbenzenes, sulfonates of naphthalenes and alkylnaphthalenes, sulfosuccinates or sulfosuccinamates. Examples of sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acid esters. Examples of phosphates are phosphate esters. Examples of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol ethoxylates.
[0816] Suitable nonionic surfactants are alkoxylates, N-substituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof. Examples of alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated with 1 to 50 equivalents. Ethylene oxide and/or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide. Examples of N-substituted fatty acid amides are fatty acid glucamides or fatty acid alkanolamides. Examples of esters are fatty acid esters, glycerol esters or monoglycerides. Examples of sugar-based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or alkylpolyglucosides. Examples of polymeric surfactants are home- or copolymers of vinylpyrrolidone, vinylalcohols, or vinylacetate.
[0817] Suitable cationic surfactants are quaternary surfactants, for example quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines. Suitable amphoteric surfactants are alkylbetains and imidazolines. Suitable block polymers are block polymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene oxide, or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide. Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinylamines or polyethyleneamines.
[0818] Suitable adjuvants are compounds, which have a neglectable or even no pesticidal activity themselves, and which improve the biological performance of the compounds of formula (I) on the target. Examples are surfactants, mineral or vegetable oils, and other auxiliaries. Further examples are listed by Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.
[0819] Suitable thickeners are polysaccharides (e.g. xanthan gum, carboxymethylcellulose), inorganic clays (organically modified or unmodified), polycarboxylates, and silicates.
[0820] Suitable bactericides are bronopol and isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazolinones.
[0821] Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea and glycerin.
[0822] Suitable anti-foaming agents are silicones, long chain alcohols, and salts of fatty acids.
[0823] Suitable colorants (e.g. in red, blue, or green) are pigments of low water solubility and water-soluble dyes. Examples are inorganic colorants (e.g. iron oxide, titan oxide, iron hexacyanoferrate) and organic colorants (e.g. alizarin-, azo- and phthalocyanine colorants).
[0824] Suitable tackifiers or binders are polyvinylpyrrolidons, polyvinylacetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, and cellulose ethers.
[0825] Examples for formulation types and their preparation are: [0826] i) Water-soluble concentrates (SL, LS) 10-60 wt % of a compound of formula (I) or a combination comprising at least one compound of formula (I) (component A) and at least one further compound selected from the herbicidal compounds B (component B) and safeners C(component C) according to the invention and 5-15 wt % wetting agent (e.g. alcohol alkoxylates) are dissolved in water and/or in a water-soluble solvent (e.g. alcohols) ad 100 wt %. The active substance dissolves upon dilution with water. [0827] ii) Dispersible concentrates (DC) 5-25 wt % of a compound of formula (I) or a combination comprising at least one compound of formula (I) (component A) and at least one further compound selected from the herbicidal compounds B (component B) and safeners C(component C) according to the invention and 1-10 wt % dispersant (e.g. polyvinylpyrrolidone) are dissolved in organic solvent (e.g. cyclohexanone) ad 100 wt %. Dilution with water gives a dispersion. [0828] iii) Emulsifiable concentrates (EC) 15-70 wt % of compound of formula (I) or a combination comprising at least one compound of formula (I) (component A) and at least one further compound selected from the herbicidal compounds B (component B) and safeners C(component C) according to the invention and 5-10 wt % emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in water-insoluble organic solvent (e.g. aromatic hydrocarbon) ad 100 wt %. Dilution with water gives an emulsion. [0829] iv) Emulsions (EW, EO, ES) 5-40 wt % of compound of formula (I) or a combination comprising at least one compound of formula (I) (component A) and at least one further compound selected from the herbicidal compounds B (component B) and safeners C(component C) according to the invention and 1-10 wt % emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in 20-40 wt % water-insoluble organic solvent (e.g. aromatic hydrocarbon). This mixture is introduced into water ad 100 wt % by means of an emulsifying machine and made into a homogeneous emulsion. Dilution with water gives an emulsion. [0830] v) Suspensions (SC, OD, FS)
[0831] In an agitated ball mill, 20-60 wt % of a compound of formula (I) or a combination comprising at least one compound of formula (I) (component A) and at least one further compound selected from the herbicidal compounds B (component B) and safeners C (component C) according to the invention are comminuted with addition of 2-10 wt % dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate), 0,1-2 wt % thickener (e.g. xanthan gum) and water ad 100 wt % to give a fine active substance suspension. Dilution with water gives a stable suspension of the active substance. For FS type formulation up to 40 wt % binder (e.g. polyvinylalcohol) is added. [0832] vi) Water-dispersible granules and water-soluble granules (WG, SG) 50-80 wt % of a compound of formula (I) or a combination comprising at least one compound of formula (I) (component A) and at least one further compound selected from the herbicidal compounds B (component B) and safeners C(component C) according to the invention are ground finely with addition of dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate) ad 100 wt % and prepared as waterdispersible or water-soluble granules by means of technical appliances (e.g. extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active substance. [0833] vii) Water-dispersible powders and water-soluble powders (WP, SP, WS) 50-80 wt % of a compound of formula (I) or a combination comprising at least one compound of formula (I) (component A) and at least one further compound selected from the herbicidal compounds B (component B) and safeners C(component C) according to the invention are ground in a rotor-stator mill with addition of 1-5 wt % dispersants (e.g. sodium lignosulfonate), 1-3 wt % wetting agents (e.g. alcohol ethoxylate) and solid carrier (e.g. silica gel) ad 100 wt %. Dilution with water gives a stable dispersion or solution of the active substance. [0834] viii) Gel (GW, GF)
[0835] In an agitated ball mill, 5-25 wt % of a compound of formula (I) or a combination comprising at least one compound of formula (I) (component A) and at least one further compound selected from the herbicidal compounds B (component B) and safeners C (component C) according to the invention are comminuted with addition of 3-10 wt % dispersants (e.g. sodium lignosulfonate), 1-5 wt % thickener (e.g. carboxymethylcellulose) and water ad 100 wt % to give a fine suspension of the active substance. Dilution with water gives a stable suspension of the active substance. [0836] iv) Microemulsion (ME)
[0837] 5-20 wt % of a compound of formula (I) or a combination comprising at least one compound of formula (I) (component A) and at least one further compound selected from the herbicidal compounds B (component B) and safeners C(component C) according to the invention are added to 5-30 wt % organic solvent blend (e.g. fatty acid dimethylamide and cyclohexanone), 10-25 wt % surfactant blend (e.g. alcohol ethoxylate and arylphenol ethoxylate), and water ad 100%. This mixture is stirred for 1 h to produce spontaneously a thermodynamically stable microemulsion. [0838] iv) Microcapsules (CS)
[0839] An oil phase comprising 5-50 wt % of a compound of formula (I) or a combination comprising at least one compound of formula (I) (component A) and at least one further compound selected from the herbicidal compounds B (component B) and safeners C (component C) according to the invention, 0-40 wt % water insoluble organic solvent (e.g. aromatic hydrocarbon), 2-15 wt % acrylic monomers (e.g. methylmethacrylate, methacrylic acid and a di- or triacrylate) are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol). Radical polymerization initiated by a radical initiator results in the formation of poly(meth)acrylate microcapsules. Alternatively, an oil phase comprising 5-50 wt % of a compound of formula (I) according to the invention, 0-40 wt % water insoluble organic solvent (e.g. aromatic hydrocarbon), and an isocyanate monomer (e.g. diphenylmethene-4,4-diisocyanate) are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol). The addition of a polyamine (e.g. hexamethylenediamine) results in the formation of polyurea microcapsules. The monomers amount to 1-10 wt %. The wt % relate to the total CS formulation. [0840] ix) Dustable powders (DP, DS)
[0841] 1-10 wt % of a compound of formula (I) or a combination comprising at least one compound of formula (I) (component A) and at least one further compound selected from the herbicidal compounds B (component B) and safeners C(component C) according to the invention are ground finely and mixed intimately with solid carrier (e.g. finely divided kaolin) ad 100 wt %. [0842] x) Granules (GR, FG)
[0843] 0.5-30 wt % of a compound of formula (I) or a combination comprising at least one compound of formula (I) (component A) and at least one further compound selected from the herbicidal compounds B (component B) and safeners C(component C) according to the invention is ground finely and associated with solid carrier (e.g. silicate) ad 100 wt %. Granulation is achieved by extrusion, spray-drying or the fluidized bed. [0844] xi) Ultra-low volume liquids (UL)
[0845] 1-50 wt % of a compound of formula (I) or a combination comprising at least one compound of formula (I) (component A) and at least one further compound selected from the herbicidal compounds B (component B) and safeners C(component C) according to the invention are dissolved in organic solvent (e.g. aromatic hydrocarbon) ad 100 wt %.
[0846] The formulation types i) to xi) may optionally comprise further auxiliaries, such as 0,1-1 wt % bactericides, 5-15 wt % anti-freezing agents, 0,1-1 wt % anti-foaming agents, and 0,1-1 wt % colorants.
[0847] The formulations and/or combinations generally comprise between 0.01 and 95%, preferably between 0.1 and 90%, and in particular between 0.5 and 75%, by weight of the compounds of formula (I).
[0848] The compounds of formula (I) are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).
[0849] Solutions for seed treatment (LS), suspoemulsions (SE), flowable concentrates (FS), powders for dry treatment (DS), water-dispersible powders for slurry treatment (WS), water-soluble powders (SS), emulsions(ES), emulsifiable concentrates (EC) and gels (GF) are usually employed for the purposes of treatment of plant propagation materials, particularly seeds. The formulations in question give, after two-to-tenfold dilution, active substance concentrations of from 0.01 to 60% by weight, preferably from 0.1 to 40% by weight, in the ready-to-use preparations. (nach unten verschoben)
[0850] Methods for applying compounds of formula (I), formulations and/or combinations thereof, on to plant propagation material, especially seeds, include dressing, coating, pelleting, dusting, soaking and in-furrow application methods of the propagation material. Preferably, compounds of formula (I), formulations and/or combinations thereof, respectively, are applied on to the plant propagation material by a method such that germination is not induced, e.g. by seed dressing, pelleting, coating and dusting.
[0851] Various types of oils, wetting agents, adjuvants, fertilizer, or micronutrients, and further pesticides (e.g. herbicides, insecticides, fungicides, growth regulators, safeners) may be added to the compounds of formula (I), the formulations and/or the combinations comprising them as premix or, if appropriate not until immediately prior to use (tank mix). These agents can be admixed with the formulations according to the invention in a weight ratio of 1:100 to 100:1, preferably 1:10 to 10:1.
[0852] The user applies the compounds of formula (I) according to the invention, the formulations and/or the combinations comprising them usually from a pre-dosage device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system. Usually, the formulation is made up with water, buffer, and/or further auxiliaries to the desired application concentration and the ready-to-use spray liquor or the formulation according to the invention is thus obtained. Usually, 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful area.
[0853] According to one embodiment, either individual components of the formulation according to the invention or partially premixed components, e.g. components comprising compounds of formula (I) and optionally active substances from the groups B and/or C), may be mixed by the user in a spray tank and further auxiliaries and additives may be added, if appropriate.
[0854] In a further embodiment, individual components of the formulation according to the invention such as parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank and further auxiliaries may be added, if appropriate.
[0855] In a further embodiment, either individual components of the formulation according to the invention or partially premixed components, e.g. components comprising compounds of formula (I) and optionally active substances from the groups B and/or C), can be applied jointly (e.g. after tank mix) or consecutively.
[0856] The compounds of formula (I), are suitable as herbicides. They are suitable as such, as an appropriate formulation or in combination with at least one further compound selected from the herbicidal active compounds B (component B) and safeners C(component C).
[0857] The compounds of formula (I), or the formulations and/or combinations comprising the compounds of formula (I), control undesired vegetation on non-crop areas very efficiently, especially at high rates of application. They act against broad-leaved weeds and grass weeds in crops such as wheat, rice, maize, soya and cotton without causing any significant damage to the crop plants. This effect is mainly observed at low rates of application.
[0858] The compounds of the invention are useful for controlling for example following weeds: Abutilon theophrasti (ABUTH), Alopercurus myosuroides (ALOMY), Amaranthus retro-flexus (AMARE), Apera spica-venti (APESV), Avena fatua (AVEFA), Digitaria sanguinalis (DIGSA), Echinocloa crus-galli (ECHCG), Lolium multiflorum (LOLMU) Setaria faberi (SETFA), Setaria viridis (SETVI), to name just a few representative examples.
[0859] The compounds of formula (I), or the formulations and/or the combinations comprising them, are applied to the plants mainly by spraying the leaves. Here, the application can be carried out using, for example, water as carrier by customary spraying techniques using spray liquor amounts of from about 100 to 1000 l/ha (for example from 300 to 400 l/ha). The compounds of formula (I), or the formulations and/or the combinations comprising them, may also be applied by the low-volume or the ultra-low-volume method, or in the form of microgranules.
[0860] Application of the compounds of formula (I), or the formulations and/or the combinations comprising them, can be done before, during and/or after, preferably during and/or after, the emergence of the undesired vegetation.
[0861] Application of the compounds of formula (I), or the formulations and/or the combinations can be carried out before or during sowing.
[0862] The compounds of formula (I), or the formulations and/or the combinations comprising them, can be applied pre-, post-emergence or pre-plant, or together with the seed of a crop plant. It is also possible to apply the compounds of formula (I), or the formulations and/or the combinations comprising them, by applying seed, pretreated with the compounds of formula (1), or the formulations and/or the combinations comprising them, of a crop plant. If the active ingredients are less well tolerated by certain crop plants, application techniques may be used in which the combinations are sprayed, with the aid of the spraying equipment, in such a way that as far as possible they do not come into contact with the leaves of the sensitive crop plants, while the active ingredients reach the leaves of undesired vegetation growing underneath, or the bare soil surface (postdirected, lay-by).
[0863] In a further embodiment, the compounds of formula (I), or the formulations and/or the combinations comprising them, can be applied by treating seed. The treatment of seeds comprises essentially all procedures familiar to the person skilled in the art (seed dressing, seed coating, seed dusting, seed soaking, seed film coating, seed multilayer coating, seed encrusting, seed dripping and seed pelleting) based on the compounds of formula (I), or the formulations and/or the combinations prepared therefrom. Here, the combinations can be applied diluted or undiluted.
[0864] The term seed comprises seed of all types, such as, for example, corns, seeds, fruits, tubers, seedlings and similar forms. Here, preferably, the term seed describes corns and seeds. The seed used can be seed of the crop plants mentioned above, but also the seed of transgenic plants or plants obtained by customary breeding methods.
[0865] When employed in plant protection, the amounts of active substances applied, i.e. the compounds of formula (I), component B and, if appropriate, component C without formulation auxiliaries, are, depending on the kind of effect desired, from 0.001 to 2 kg per ha, preferably from 0.005 to 2 kg per ha, more preferably from 0.05 to 0.9 kg per ha and in particular from 0.1 to 0.75 kg per ha.
[0866] In another embodiment of the invention, the application rate of the compounds of formula (I), component B and, if appropriate, component C, is from 0.001 to 3 kg/ha, preferably from 0.005 to 2.5 kg/ha and in particular from 0.01 to 2 kg/ha of active substance (a.s.).
[0867] In another preferred embodiment of the invention, the rates of application of the compounds of formula (I) according to the present invention (total amount of compounds of formula (I)) are from 0.1 g/ha to 3000 g/ha, preferably 10 g/ha to 1000 g/ha, depending on the control target, the season, the target plants and the growth stage.
[0868] In another preferred embodiment of the invention, the application rates of the compounds of formula (I) are in the range from 0.1 g/ha to 5000 g/ha and preferably in the range from 1 g/ha to 2500 g/ha or from 5 g/ha to 2000 g/ha.
[0869] In another preferred embodiment of the invention, the application rate of the compounds of formula (I) is 0.1 to 1000 g/ha, preferablyl to 750 g/ha, more preferably 5 to 500 g/ha.
[0870] The required application rates of herbicidal compounds B are generally in the range of from 0.0005 kg/ha to 2.5 kg/ha and preferably in the range of from 0.005 kg/ha to 2 kg/ha or 0.01 kg/ha to 1.5 kg/h of a.s.
[0871] The required application rates of safeners C are generally in the range of from 0.0005 kg/ha to 2.5 kg/ha and preferably in the range of from 0.005 kg/ha to 2 kg/ha or 0.01 kg/ha to 1.5 kg/h of a.s.
[0872] In treatment of plant propagation materials such as seeds, e.g. by dusting, coating or drenching seed, amounts of active substance of from 0.1 to 1000 g, preferably from 1 to 1000 g, more preferably from 1 to 100 g and most preferably from 5 to 100 g, per 100 kilogram of plant propagation material (preferably seeds) are generally required.
[0873] In another embodiment of the invention, to treat the seed, the amounts of active substances applied, i.e. the compounds of formula (I), component B and, if appropriate, component C are generally employed in amounts of from 0.001 to 10 kg per 100 kg of seed.
[0874] When used in the protection of materials or stored products, the amount of active substance applied depends on the kind of application area and on the desired effect.
[0875] Amounts customarily applied in the protection of materials are 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of active substance per cubic meter of treated material.
[0876] In case of combinations according to the present invention it is immaterial whether the compounds of formula (I), and the further component B and/or the component C are formulated and applied jointly or separately.
[0877] In the case of separate application, it is of minor importance, in which order the application takes place. It is only necessary, that the compounds of formula (I), and the further component B and/or the component C are applied in a time frame that allows simultaneous action of the active ingredients on the plants, preferably within a time-frame of at most 14 days, in particular at most 7 days.
[0878] Depending on the application method in question, the compounds of formula (I), or the formulations and/or combinations comprising them, can additionally be employed in a further number of crop plants for eliminating undesired vegetation. Examples of suitable crops are the following: [0879] Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Avena sativa, Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. silvestris, Brassica oleracea, Brassica nigra, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Manihot esculenta, Medicago sativa, Musa spec., Nicotiana tabacum (N.rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec., Pistacia vera, Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Prunus armeniaca, Prunus cerasus, Prunus dulcis and Prunus domestica, Ribes sylvestre, Ricinus communis, Saccharum officinarum, Secale cereale, Sinapis alba, Solanum tuberosum, Sorghum bicolor (s. vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticale, Triticum durum, Vicia faba, Vitis vinifera and Zea mays. [0880] Preferred crops are Arachis hypogaea, Beta vulgaris spec. altissima, Brassica napus var. napus, Brassica oleracea, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cynodon dactylon, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hordeum vulgare, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Medicago sativa, Nicotiana tabacum (N.rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Pistacia vera, Pisum sativum, Prunus dulcis, Saccharum officinarum, Secale cereale, Solanum tuberosum, Sorghum bicolor (s. vulgare), Triticale, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera and Zea mays.
[0881] Especially preferred crops are crops of cereals, corn, soybeans, rice, oilseed rape, cotton, potatoes, peanuts or permanent crops.
[0882] The compounds of formula (I) according to the invention, or the formulations and/or combinations comprising them, can also be used in crops which have been modified by mutagenesis or genetic engineering in order to provide a new trait to a plant or to modify an already present trait.
[0883] The term crops as used herein includes also (crop) plants which have been modified by mutagenesis or genetic engineering in order to provide a new trait to a plant or to modify an already present trait.
[0884] Mutagenesis includes techniques of random mutagenesis using X-rays or mutagenic chemicals, but also techniques of targeted mutagenesis, in order to create mutations at a specific locus of a plant genome. Targeted mutagenesis techniques frequently use oligonucleotides or proteins like CRISPR/Cas, zinc-finger nucleases, TALENs or meganucleases to achieve the targeting effect.
[0885] Genetic engineering usually uses recombinant DNA techniques to create modifications in a plant genome which under natural circumstances cannot readily be obtained by cross breeding, mutagenesis or natural recombination. Typically, one or more genes are integrated into the genome of a plant in order to add a trait or improve a trait. These integrated genes are also referred to as transgenes in the art, while plant comprising such transgenes are referred to as transgenic plants. The process of plant transformation usually produces several transformation events, which differ in the genomic locus in which a transgene has been integrated. Plants comprising a specific transgene on a specific genomic locus are usually described as comprising a specific event, which is referred to by a specific event name. Traits which have been introduced in plants or have been modified include in particular herbicide tolerance, insect resistance, increased yield and tolerance to abiotic conditions, like drought.
[0886] Herbicide tolerance has been created by using mutagenesis as well as using genetic engineering. Plants which have been rendered tolerant to acetolactate synthase (ALS) inhibitor herbicides by conventional methods of mutagenesis and breeding comprise plant varieties commercially available under the name Clearfield. However, most of the herbicide tolerance traits have been created via the use of transgenes.
[0887] Herbicide tolerance has been created to glyphosate, glufosinate, 2,4-D, dicamba, oxynil herbicides, like bromoxynil and ioxynil, sulfonylurea herbicides, ALS inhibitor herbicides and 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors, like isoxaflutole and mesotrione.
[0888] Transgenes which have been used to provide herbicide tolerance traits comprise: for tolerance to glyphosate: cp4 epsps, epsps grg23ace5, mepsps, 2mepsps, gat4601, gat4621 and goxv247, for tolerance to glufosinate: pat and bar, for tolerance to 2,4-D: aad-1 and aad-12, for tolerance to dicamba: dmo, for tolerance to oxynil herbicies: bxn, for tolerance to sulfonylurea herbicides: zm-hra, csr1-2, gm-hra, S4-HrA, for tolerance to ALS inhibitor herbicides: csr1-2, for tolerance to HPPD inhibitor herbicides: hppdPF, W336 and avhppd-03.
[0889] Transgenic corn events comprising herbicide tolerance genes are for example, but not excluding others, DAS40278, MON801, MON802, MON809, MON810, MON832, MON87411, MON87419, MON87427, MON88017, MON89034, NK603, GA21, MZHGOJG, HCEM485, VCO-1981-5, 676, 678, 680, 33121, 4114, 59122, 98140, Bt10, Bt176, CBH-351, DBT418, DLL25, MS3, MS6, MZIR098, T.sub.25, TC1507 and TC6275.
[0890] Transgenic soybean events comprising herbicide tolerance genes are for example, but not excluding others, GTS 40-3-2, MON87705, MON87708, MON87712, MON87769, MON89788, A2704-12, A2704-21, A5547-127, A5547-35, DP356043, DAS44406-6, DAS68416-4, DAS-81419-2, GU262, SYHTH.sub.2, W62, W98, FG72 and CV127.
[0891] Transgenic cotton events comprising herbicide tolerance genes are for example, but not excluding others, 19-51a, 31707, 42317, 81910, 281-24-236, 3006-210-23, BXN10211, BXN10215, BXN10222, BXN 10224, MON1445, MON1698, MON88701, MON88913, GHB119, GHB614, LLCotton25, T303-3 and T304-40.
[0892] Transgenic canola events comprising herbicide tolerance genes are for example, but not excluding others, MON88302, HCR-1, HCN10, HCN28, HCN92, MS1, MS8, PHY14, PHY23, PHY35, PHY36, RF1, RF2 and RF3.
[0893] Insect resistance has mainly been created by transferring bacterial genes for insecticidal proteins to plants. Transgenes which have most frequently been used are toxin genes of Bacillus spec. and synthetic variants thereof, like crylA, crylAb, crylAb-Ac, crylAc, crylA.105, crylF, crylFa2, cry2Ab2, cry2Ae, mcry3A, ecry3.1Ab, cry3Bb1, cry34Ab1, cry35Ab1, cry9C, vip3A (a), vip3Aa20. However, also genes of plant origin have been transferred to other plants. In particular genes coding for protease inhibitors, like CpTI and pinll. A further approach uses transgenes in order to produce double stranded RNA in plants to target and downregulate insect genes. An example for such a transgene is dvsnf7.
[0894] Transgenic corn events comprising genes for insecticidal proteins or double stranded RNA are for example, but not excluding others, Bt10, Bt11, Bt176, MON801, MON802, MON809, MON810, MON863, MON87411, MON88017, MON89034, 33121, 4114, 5307, 59122, TC1507, TC6275, CBH-351, MIR162, DBT418 and MZIR098.
[0895] Transgenic soybean events comprising genes for insecticidal proteins are for example, but not excluding others, MON87701, MON87751 and DAS-81419.
[0896] Transgenic cotton events comprising genes for insecticidal proteins are for example, but not excluding others, SGK321, MON531, MON757, MON1076, MON15985, 31707, 31803, 31807, 31808, 42317, BNLA-601, Event1, COT67B, COT102, T303-3, T.sub.304-40, GFM CrylA, GK12, MLS 9124, 281-24-236, 3006-210-23, GHB119 and SGK321. Increased yield has been created by increasing ear biomass using the transgene athb17, being present in corn event MON87403, or by enhancing photosynthesis using the transgene bbx32, being present in the soybean event MON87712.
[0897] Crops comprising a modified oil content have been created by using the transgenes: gm-fad2-1, Pj.D6D, Nc.Fad3, fad2-1A and fatb1-A. Soybean events comprising at least one of these genes are: 260-05, MON87705 and MON87769.
[0898] Tolerance to abiotic conditions, in particular to tolerance to drought, has been created by using the transgene cspB, comprised by the corn event MON87460 and by using the transgene Hahb-4, comprised by soybean event IND-410-5.
[0899] Traits are frequently combined by combining genes in a transformation event or by combining different events during the breeding process. Preferred combination of traits are herbicide tolerance to different groups of herbicides, insect tolerance to different kind of insects, in particular tolerance to lepidopteran and coleopteran insects, herbicide tolerance with one or several types of insect resistance, herbicide tolerance with increased yield as well as a combination of herbicide tolerance and tolerance to abiotic conditions.
[0900] Plants comprising singular or stacked traits as well as the genes and events providing these traits are well known in the art. For example, detailed information as to the mutagenized or integrated genes and the respective events are available from websites of the organizations International Service for the Acquisition of Agri-biotech Applications (ISAAA) (http://www.isaaa.org/gmapprovaldatabase) and the Center for Environmental Risk Assessment (CERA) (http://cera-gmc.org/GMCropDatabase), as well as in patent applications, like EP3028573 and WO2017/011288.
[0901] The use of the compounds of formula (I) or formulations or combinations comprising them according to the invention on crops may result in effects which are specific to a crop comprising a certain gene or event. These effects might involve changes in growth behavior or changed resistance to biotic or abiotic stress factors. Such effects may in particular comprise enhanced yield, enhanced resistance or tolerance to insects, nematodes, fungal, bacterial, mycoplasma, viral or viroid pathogens as well as early vigor, early or delayed ripening, cold or heat tolerance as well as changed amino acid or fatty acid spectrum or content.
[0902] Furthermore, plants are also covered that contain by the use of recombinant DNA techniques a modified amount of ingredients or new ingredients, specifically to improve raw material production, e.g., potatoes that produce increased amounts of amylopectin (e.g. Amflora potato, BASF SE, Germany).
[0903] Furthermore, it has been found that the compounds of formula (I) according to the invention, or the formulations and/or combinations comprising them, are also suitable for the defoliation and/or desiccation of plant parts of crops such as cotton, potato, oilseed rape, sunflower, soybean or field beans, in particular cotton. In this regard, formulations and/or combinations for the desiccation and/or defoliation of crops, processes for preparing these formulations and/or combinations and methods for desiccating and/or defoliating plants using the compounds of formula (I) have been found.
[0904] As desiccants, the compounds of formula (I) are particularly suitable for desiccating the above-ground parts of crop plants such as potato, oilseed rape, sunflower and soybean, but also cereals. This makes possible the fully mechanical harvesting of these important crop plants.
[0905] Also of economic interest is to facilitate harvesting, which is made possible by concentrating within a certain period of time the dehiscence, or reduction of adhesion to the tree, in citrus fruit, olives and other species and varieties of pernicious fruit, stone fruit and nuts. The same mechanism, i.e. the promotion of the development of abscission tissue between fruit part or leaf part and shoot part of the plants is also essential for the controlled defoliation of useful plants, in particular cotton.
[0906] Moreover, a shortening of the time interval in which the individual cotton plants mature leads to an increased fiber quality after harvesting.
A Synthesis Examples
[0907] Chemical bonds, drawn as bars in chemical formulae, indicate the relative stereochemistry on the ring system.
Example 1: Synthesis of Methyl (3S)-3-[3-(3-Chloroanilino)-2,2-Dimethyl-3-Oxopropanoyl]Amino]Butanoate
[0908] ##STR00027##
[0909] 1.1 Lithium 3-ethoxy-2,2-dimethyl-3-oxo-propanoate:
##STR00028##
[0910] Diethyl 2,2-dimethylpropanedioate (20.0 g; 106 mmol) was dissolved in a mixture of THF (50 mL) and water (50 mL). Lithium hydroxide (2.55 g; 106 mmol) was added in portions. The reaction mixture was stirred at room temperature for 60 hours. The solution was concentrated in vacuo and dried in vacuum drying cabinet over night at 50 C. to give the crude product (9.90 g) which was used without further purification for the next step.
[0911] 1.2 Ethyl 3-(3-chloroanilino)-2,2-dimethyl-3-oxo-propanoate:
##STR00029##
[0912] A mixture of 3-chloroaniline (1.84 g; 14.5 mmol; 1.2 eq), an aliquot of the crude lithium salt of 3-ethoxy-2,2-dimethyl-3-oxo-propanoate (2.00 g; 12.0 mmol; 1 eq) and triethylamine (3.66 g; 36.1 mmol; 3 eq) in THF (20 mL) was treated with n-propanephosphonic acid anhydride (13.0 g; 20.5 mmol; 1.7 eq; 50% solution in ethyl acetate; T.sub.3P; CAS [68957-94-8]) and stirred overnight at room temperature. Water (30 mL) was added, and the reaction mixture extracted with ethyl acetate. The organic solution was washed with aqueous hydrochloric acid solution (1 M) and water, dried over sodium sulfate and concentrated in vacuo to give crude ethyl 3-(3-chloroanilino)-2,2-dimethyl-3-oxopropanoate (3.10 g) which was again used for the next step without further purification.
[0913] 1.3 3-(3-Chloroanilino)-2,2-dimethyl-3-oxo-propanoic acid:
##STR00030##
[0914] Crude ethyl 3-(3-chloroanilino)-2,2-dimethyl-3-oxo-propanoate (3.10 g; 11.5 mmol) was dissolved in a mixture of THF (20 mL) and water (20 mL). Lithium hydroxide (0.551 g; 23.0 mmol; 2 eq) was added in portions. The reaction mixture was stirred at room temperature for 3 hours. The THF was evaporated in vacuo and the slurry was treated with methyl tert-butyl ether and the resulting two phases were separated. The aqueous solution was adjusted to ca. pH 1 with concentrated hydrochloric acid solution. The product 3-(3-chloroanilino)-2,2-dimethyl-3-oxo-propanoic acid precipitated overnight and was filtered. (0.80 g; 29% yield).
[0915] .sup.1H NMR: (400 MHz; DMSO) =12.7 (br s, 1H), 9.65 (s, 1H), 7.85 (s, 1H), 7.55 (d, 1H), 7.30 (t, 1H), 7.10 (d, 1H), 1.40 (s, 6H)
[0916] 1.4 Methyl (3S)-3-[3-(3-chloroanilino)-2,2-dimethyl-3-oxo-propanoyl]amino]butanoate
##STR00031##
[0917] To a solution of 3-(3-chloroanilino)-2,2-dimethyl-3-oxo-propanoic acid (250 mg, 1.03 mmol) in dimethylformamide (DMF, 5 ml) methyl (3S)-3-aminobutanoate (Shomoalanine) hydrochloride (194 mg, 1.19 mmol) was added. To the resulting solution was added HATU (2-(7-aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate, CAS [148893 Oct. 1]), (452 mg, 1.19 mmol) and then diisopropylethylamine (257 mg, 2.07 mmol)). The resulting reaction mixture was stirred at room temperature for a few hours. Water and ethyl acetate were added. The ethyl acetate phase was washed with saturated sodium chloride solution and the solvent evaporated under reduced pressure. The crude product was purified by reversed phase chromatography using acetonitrile/water as eluent. This gave 190 mg (54%) of the product. .sup.1H NMR: (400 MHZ, CDCl.sub.3) d=9.55 (s, 1H), 7.75 (s, 1H), 7.4 (d, 1H), 7.25 (t, 1H), 7.1 (d, 1H), 6.95 (1 H), 4.35 (m, 1H), 3.7 (s, 3H), 2.55 (q, 2H), 1.55 (s, 6H), 1.25 (d, 3H).
[0918] In analogy to the examples described above, the following compounds of formula (I), wherein R.sup.1, R.sup.2, R.sup.6 and R.sup.9 are hydrogen and R.sup.3, R.sup.4, R.sup.5, R.sup.7, R.sup.8 and X-Y (depicted together with the nitrogen atom to which-X-Y is bound to show the stereochemistry) are compiled in Table 1, were prepared, starting from commercially available diesters and using commercially available amines:
##STR00032##
TABLE-US-00002 TABLE 1 No. R.sup.3 R.sup.4 R.sup.5 R.sup.7 R.sup.8 N* XY LC-MS I.1. Cl H Cl CH.sub.3 CH.sub.3
[0919] The herbicidal activity of the compounds of formula (I) was demonstrated by the following greenhouse experiments:
[0920] The culture containers used were plastic flowerpots containing loamy sand with approximately 3.0% of humus as the substrate. The seeds of the test plants were sown separately for each species.
[0921] For the pre-emergence treatment, the active ingredients, which had been suspended or emulsified in water, were applied directly after sowing by means of finely distributing nozzles. The containers were irrigated gently to promote germination and growth and subsequently covered with transparent plastic hoods until the test plants had rooted. This cover caused uniform germination of the test plants, unless this had been impaired by the active ingredients.
[0922] For the post-emergence treatment, the test plants were first grown to a height of 3 to 15 cm, depending on the plant habit, and only then treated with the active ingredients which had been suspended or emulsified in water. For this purpose, the test plants were either sown directly and grown in the same containers, or they were first grown separately as seedlings and transplanted into the test containers a few days prior to treatment.
[0923] Depending on the species, the test plants were kept at 10-25 C. or 20-35 C., respectively.
[0924] The test period extended over 2 to 4 weeks. During this time, the test plants were tended, and their response to the individual treatments was evaluated.
[0925] Evaluation was carried out using a scale from 0 to 100. 100 means no emergence of the test plants, or complete destruction of at least the aerial moieties, and 0 means no damage, or normal course of growth. A good herbicidal activity is given at values of 70 to <90 and a very good herbicidal activity is given at values of 90 to 100.
[0926] The test plants used in the greenhouse experiments were of the following species:
TABLE-US-00003 Bayer code Scientific name ABUTH Abutilon theophrasti ALOMY Alopercurus myosuroides AMARE Amaranthus retroflexus APESV Apera spica-venti AVEFA Avena fatua DIGSA Digitaria sanguinalis ECHCG Echinocloa crus-galli LOLMU Lolium multiflorum SETFA Setaria faberi SETVI Setaria viridis
[0927] At an application rate of 0.250 kg/ha, applied by the pre-emergence method: [0928] compound 1.19 showed good herbicidal activity against ABUTH [0929] compounds 1.2, 1.9, 1. 17 showed good herbicidal activity against AMARE. [0930] compounds 1.24, 1.78 showed very good herbicidal activity against DIGSA [0931] compound 1.79 showed good herbicidal activity against DIGSA [0932] compounds 1.9, 1.15, 1.18 showed very good herbicidal activity against ECHCG [0933] compounds 1.2, 1.12 showed good herbicidal activity against ECHCG. [0934] compounds 1.24, 1.78, 1.79 showed very good herbicidal activity against LOLMU [0935] compound 1.80 showed good herbicidal activity against LOLMU. [0936] compounds 1.2, 1.7, 1.9, 1.18, 1.20 showed very good herbicidal activity against SETFA. [0937] compounds 1.12, 1.16, 1. 19 showed good herbicidal activity against SETFA [0938] compound 1.24 showed very good herbicidal activity against SETVI [0939] compound 1.78 showed very good herbicidal activity against SETVI
[0940] At an application rate of 0.250 kg/ha, applied by the post-emergence method: [0941] compounds 1.2, 1.9, 1.18 showed very good herbicidal activity against ABUTH. [0942] compounds 1.4 showed good herbicidal activity against ABUTH. [0943] compounds 1.2, 1.4, 1.15, 1.18, 1.19, 1.22, 1.78, 1.79, 1.80 showed very good herbicidal activity against ALOMY [0944] compounds 1.3, 1.6, 1.10, 1.11, 1.12, 1.14, 1.16, 1.21, 1.24 showed good herbicidal activity against ALOMY. [0945] compounds 1.15, 1.78, 1.79, 1.80 showed very good herbicidal activity against AMARE [0946] compounds 1.3, 1.12 showed good herbicidal activity against AMARE [0947] compounds 1.3, 1.9, 1.19, 1.21, 1.22, 1.24, 1.79, 1.80 showed very good herbicidal activity against AVEFA. [0948] compounds 1.5, 1.6, 1.10, 1.11, 1.14, 1.16, 1.17, 1.20 showed good herbicidal activity against AVEFA. [0949] compounds 1.2, 1.4, 1.9, 1.12, 1.15, 1.18, 1.24, 1.78 showed very good herbicidal activity against ECHCG [0950] compounds 1.20, 1.23 showed good herbicidal activity against ECHCG [0951] compounds 1.20, 1.22, 1.23 showed good herbicidal activity against SETVI
[0952] At an application rate of 0.500 kg/ha, applied by the pre-emergence method: [0953] compounds 1.1 showed very good herbicidal activity against APESV [0954] compounds 1.1 showed good herbicidal activity against ABUTH
[0955] At an application rate of 0.500 kg/ha, applied by the post-emergence method: [0956] compounds 1.1 showed very good herbicidal activity against ALOMY [0957] compounds 1.1 showed very good herbicidal activity against AVEFA. [0958] compounds 1.1 showed very good herbicidal activity against SETVI