Isoxazolyl- and pyrazolyl-benzoyl and bicyclic benzoyl derivatives having herbicidal activity are known and are described, for example, in WO 96/26192, WO 96/26206 and WO 97/08164.

New substituted bicyclic benzoyl derivatives having herbicidal and growth-inhibiting properties have now been found.

The present invention therefore relates to compounds of formula I wherein R1 is C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy-C1-C4alkyl, C1-C4alkoxycarbonyl, cyano, cyano- C1-C4alkyl, hydroxy-C1-C4alkyl, amino-C1-C4alkyl, CHO, C,-C4alkyl-ON=CH, C2-C6alkenyl, C1-O4alkoxycarbonyl-C2-C6alkenyl or a group CH(OR20)OR21 R20 and R21 are each independently of the other C1-C4alkyl; or R20 and R21 together are -(CH2)n1-; n1 is 2, 3 or 4; R2 is hydrogen or C1-C4alkyl; R3 and R4 are each independently of the other hydrogen, C1-C4alkyl or halogen; n is 0,1 or 2; R5 is C1-C4alkyl, C1-C4haloalkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkyl-S(O)n2, (C1 -C4alkyl)2NS(O)2, C1-C4alkyl-S(O)2O, halogen, nitro or cyano; n2 is 0,1 or2; Q is OH, halogen or a group R6 and R7 are each independently of the other hydrogen, OH, C1-C4alkyl, C2-C6alkenyl, C2-C6alkynyl, Ci -C4alkoxycarbonyl, C1-C4alkyl-S(O)n2, C1-C4alkyl-NHS(O)2, phenyl or phenyl substituted by C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylcarbonyl, C1-C4alkoxycarbonyl, amino, C1-C4alkylamino, di-C1-C4alkylamino, C1-C4alkyl-S(O)n2, C1-C4alkyl-S(O)2O, C1-C4haloalkyl-S(O)n2, C1-C4haloalkyl-S(0)20, C1-C4alkyl-S(0)2NH, C1-C4alkyl-S(O)2N(C1 -C4alkyl), halogen, nitro, COOH or cyano; or R6 and R7 are each independently of the other C1-C4haloalkyl, -NH-C1-C4alkyl, -N(C1-C4alkyl)2, C1-C6alkoxy, cyano, nitro or halogen; or adjacent R6 and R7 together are -(CH2)n3-; n3 is 2, 3, 4, 5 or 6; W is oxygen, sulfur, -C(R18)2- or -N(R22)-; n6 is 0 or 1, or when W is -C(R18)2-, n6 may additionally be 2 or 3; each R18 independently of the other is hydrogen, C1-C4alkyl, C1-C4haloalkyl or C1-C4alkoxy- carbonyl; or R18 together with one of the adjacent substituents R7 forms a single bond when n6 is 1, and the remaining geminal R6 and R7 are other than hydrogen; R22 is hydrogen, C1-C4alkyl or C1-C4alkoxycarbonyl; Ra is OH, C1-C4alkoxy, C1-C4alkylcarbonyloxy, C1-C4alkoxycarbonyloxy, R23R24N-C(O)O, phenylthio, C1-C4alkylthio, C1-C4alkyl-S(O)2O, (C1-C4alkoxy)2P(O)O, C1-C4alkyl(C1-C4- alkoxy)P(O)O, H(C1-C4alkoxy)P(O)O or benzoyloxy; R23 and R24 are each independently of the other hydrogen or C1-C4alkyl; Y is oxygen, sulfur or -(CH2)n5-; n5 is 0, 1, 2, 3 or 4; Rg is hydrogen, C,-C6alkyl, C1-C4alkylcarbonyl, C1 -C4alkoxycarbonyl, (C1-C4alkyl)NHCO or (C1-C4alkyl)2NCO; R10, nil and R12 are each independently of the others hydrogen, C1-C4alkyl, C1-C4alkoxy- carbonyl, phenyl or phenyl substituted by C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4- haloalkoxy, C1-C4alkylcarbonyl, C1-C4alkoxycarbonyl, amino, C1-C4alkylamino, di-C1-C4alkyl- amino, C1-C4alkyl-S(O)n2, C1-C4alkyl-S(O)2O, C1-C4haloalkyl-S(O)n2, C1-C4haloalkyl-S(O)2O, C1-C4alkyl-S(O)2NH, C1-C4alkyl-S(O)2N(C1 -C4alkyl), halogen, nitro, COOH or cyano; R13 is hydrogen; halogen; C1-C4alkyl; C1-C4alkyl substituted by unsubstituted or R17- substituted phenyl; C1-C4haloalkyl; C2-C6alkenyl; C2-C6alkenyl substituted by unsubstituted or R17-substituted phenyl; C2-Cealkynyl; C2-C6alkynyl substituted by unsubstituted or R17- substituted phenyl; C3-C6haloalkenyl; C3-C6haloalkynyl; C3-C6cycloalkyl; C3-C6cycloalkyl substituted by halogen, R15 or COOR16; COOR16; COR15; cyano; nitro; CONH2; (C,-C4- alkyl)NHCO; (C1-C4alkyl)2NCO; (C1-C4haloalkyl)NHCO; (C1-C4haloalkyl)2NCO; C1-C4alkyl- S(O)n2; C1-C4alkyl-S(O)n2 substituted by unsubstituted or R17-substituted phenyl; C1-C4- alkoxy-C2-C6alkyl-S(O)n2; C2-C6alkenyl-S(O)n2; C2-C6alkenyl-S(O)n2 substituted by unsubstituted or R17-substituted phenyl; C2-C6alkynyl-S(O)n2; or C2-C6alkynyl-S(O)n2 substituted by unsubstituted or R17-substituted phenyl; R15 is C1-C4alkyl, C1-C4haloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, C3-C6halo- alkynyl, phenyl or R17-substituted phenyl; R16 is hydrogen, C1-C4alkyl or C,-C4haloalkyl; R17 is halogen, C1-C4alkyl, C1-C4haloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl, C1 -C4alkoxy-C1 -C4alkyl, C1 -C4alkoxy-C3-C6alkenyl, C,-C4alkoxy-C3-C6- alkynyl, cyano, nitro, COOH, C1-C4alkoxycarbonyl, C1-C4haloalkoxycarbonyl, C,-C4alkyl- S(O)n2, C1-C4haloalkyl-S(O)n2, phenyl-S(O)n2; phenyl-S(O)n2 substituted on the phenyl ring by halogen, C1-C4alkyl, C1-C4haloalkyl, C3-C6alkenyl, C3-C6alkynyl, cyano, nitro, COOH, C1-C4- alkoxycarbonyl, C1-C4alkyl-S(O)n2, C1-C4haloalkyl-S(O)n2, C1-C4alkylcarbonyl,di-C1-C4alkyl- amino, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkyl-S(O)2O or C1-C4haloalkyl-S(O)2O; C1-C4- alkylcarbonyl, di-C1 -C4alkylamino, C1-C4alkyl-S(O)2NH, C1-C4alkyl-S(O)2N(C1-C4alkyl), C1-C4haloalkyl-S(O)2NH, C1 -C4haloalkyl-S(0)2N(C1-C4alkyl), NH2S(O)2, (C1-C4alkyl)NHS(O)2, (C1-C4alkyl)2NS(O)2, CONH2, (C1 -C4alkyl)NHCO, (C1-C4alkyl)2NCO, NH2CS, (C1-C4alkyl)NHCS, (C1-C4alkyl)2NCS, C1-C4alkoxy, C1-C4haloalkoxy, C3-C6alkenyloxy, C3-C6alkynyloxy, C1-C4alkyl-S(O)2O, C1-C4haloalkyl-S(O)2O, phenyl-S(O)2O or phenyl- S(O)2O substituted on the phenyl ring by halogen, C1-C4alkyl, C1-C4haloalkyl, C3-C6alkenyl, C3-C6alkynyl, cyano, nitro, COOH, C1-C4alkoxycarbonyl, C1-C4alkyl-S(O)n2, C1-C4haloalkyl- S(O)n2, C1-C4alkylcarbonyl, di-C1-C4alkylamino, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkyl- S(O)2O or C1-C4haloalkyl-S(O)2O; and R14 is C1 -C4alkyl, C1-C4haloaikyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, C3-C6halo- alkynyl, C3-C6cycloalkyl or C3-C6cycloalkyl substituted by halogen, C1-C4alkyl, C1-C4halo- alkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl, phenyl or phenyl substituted by halogen, C1-C4alkyl, C1-C4haloalkyl, C3-C6alkenyl, C3-C6alkynyl, cyano, nitro, COOH, C1-C4alkoxycarbonyl, C1-C4alkyl-S(O)n2, C1-C4haloalkyl-S(O)n2, C1-C4alkylcarbonyl, di-C1-C4alkylamino, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkyl-S(O)2O or C,-C4haloalkyl- S(0)20, and the agrochemically acceptable salts and stereoisomers of those compounds of formula I.

In the above definitions, halogen is to be understood as meaning iodine or, preferably, fluorine, chlorine or bromine.

The alkyl, alkenyl and alkynyl groups in the substituent definitions may be straight-chain or branched, this applying also to the alkyl, alkenyl and alkynyl moiety of the following groups: alkylcarbonyl, cyanoalkyl, alkoxyalkyl, alkylthio, alkylsulfonyl, alkylaminocarbonyl, dialkyl- aminocarbonyl, (alkyl)2NS(O)2, alkyl(alkoxy)P(O)O, alkyl substituted by unsubstituted or R17- substituted phenyl, alkenyl substituted by unsubstituted or R17-substituted phenyl, alkoxy- carbonylalkenyl, alkylS(O)2N(alkyl), (alkyl)2NCO, (alkyl)2NCS ,alkenyl-S(O)n2 substituted by unsubstituted or R17-substituted phenyl, alkoxyalkenyl, alkenyloxy and alkynyloxy.

Alkyl groups are, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl and the various isomers of pentyl and hexyl. Methyl, ethyl, n-propyl, isopropyl and n-butyl are preferred.

Examples of alkenyl radicals that may be mentioned are vinyl, allyl, methallyl, 1-methylvinyl, but-2-en-1-yl, pentenyl and 2-hexenyl, with preference being given to alkenyl radicals having a chain length of from 3 to 5 carbon atoms.

Examples of alkynyl radicals that may be mentioned are ethynyl, propargyl, 1-methyl- propargyl, 3-butynyl, but-2-yn-1 -yl, 2-methylbut-3-yn-2-yl, but-3-yn-2-yl, 1 -pentynyl, pent-4- yn-1-yl and 2-hexynyl, with preference being given to alkynyl radicals having a chain length of from 2 to 4 carbon atoms.

Suitable haloalkyl radicals are alkyl groups that are mono- or poly-substituted, especially mono- to tri-substituted, by halogen, halogen being in particular iodine or especially fluorine, chlorine or bromine, for example fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2-chloroethyl, 2,2-dichloro- ethyl, 2,2,2-trifluoroethyl and 2,2,2-trichloroethyl.

Suitable haloalkenyl radicals are alkenyl groups mono- or poly-substituted by halogen, halogen being in particular bromine, iodine or especially fluorine or chlorine, for example 2- or 3-fluoropropenyl, 2- or 3-chloropropenyl, 2- or 3-bromopropenyl, 2,3,3-trifluoropropenyl, 2,3,3-trichloropropenyl, 4,4,4-trifluorobut-2-en-1 -yl and 4,4,4-trichlorobut-2-en-1 -yl. Of the alkenyl radicals mono-, di- or tri-substituted by halogen, preference is given to those having a chain length of 3 or 4 carbon atoms. The alkenyl groups may be substituted by halogen at saturated or unsaturated carbon atoms.

Suitable haloalkynyl radicals are, for example, alkynyl groups mono- or poly-substituted by halogen, halogen being bromine, iodine or especially fluorine or chlorine, for example 3- fluoropropynyl, 3-chloropropynyl, 3-bromopropynyl, 3,3,3-trifluoropropynyl and 4,4,4- trifluoro-but-2-yn-1 -yl .

Alkylsulfonyl is, for example, methylsulfonyl, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl, sec-butylsulfonyl, tert-butylsulfonyl or an isomer of pentyl- sulfonyl or hexylsulfonyl; preferably methylsulfonyl or ethylsulfonyl.

Haloalkylsulfonyl is, for example, fluoromethylsulfonyl, difluoromethylsulfonyl, trifluoro- methylsulfonyl, chloromethylsulfonyl, trichloromethylsulfonyl, 2-fluoroethylsulfonyl, 2,2,2-tri- fluoroethylsulfonyl or 2,2,2-trichloroethylsulfonyl.

Alkenylsulfonyl is, for example, allylsulfonyl, methallylsulfonyl, but-2-en-1 -ylsulfonyl, pentenylsulfonyl or 2-hexenylsulfonyl.

Cyanoalkyl is, for example, cyanomethyl, cyanoethyl, cyanoeth-1-yl or cyanopropyl.

Alkylamino is, for example, methylamino, ethyiamino or an isomer of propyl- or butyl-amino.

Dialkylamino is, for example, dimethylamino, diethylamino or an isomer of dipropyl- or dibutyl-amino.

Alkylcarbonyl is especially acetyl or propionyl.

Alkoxy is, for example, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec- butoxy or tert-butoxy.

Alkenyloxy is, for example, allyloxy, methallyloxy or but-2-en-1 -yloxy.

Alkynyloxy is, for example, propargyloxy or 1-methylpropargyloxy.

Alkoxyalkyl is, for example, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, n-propoxymethyl, n-propoxyethyl, isopropoxymethyl or isopropoxyethyl.

Alkoxycarbonyl is, for example, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, iso- propoxycarbonyl or n-butoxycarbonyl, preferably methoxycarbonyl or ethoxycarbonyl.

Haloalkoxy is, for example, fluoromethoxy, difluoromethoxy, trifluoromethoxy, 2,2,2-trifluoro- ethoxy, 1,1 ,2,2-tetrafluoroethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2,2,2-trichloroethoxy or pentafluoroethoxy.

The cycloalkyl radicals suitable as substituents are, for example, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.

The halocycloalkyl radicals suitable as substituents are, for example, mono-, di- or per- halogenated cycloalkyl radicals, for example fluorocyclopropyl, chlorocyclopropyl, bromo- cyclopropyl, 2,2-dichlorocyclopropyl, 2,2-difluorocyclopropyl, 2,2-dibromocyclopropyl, 2- fluoro-2-chlorocyclopropyl, 2-chloro-2-bromocyclopropyl, 2,2,3,3-tetrafluorocyclop ropyl, 2,2,3,3-tetrachlorocyclopropyl, pentafluorocyclopropyl, fluorocyclobutyl, chlorocyclobutyl, 2,2-difluorocyclobutyl, 2,2,3,3-tetrafluorocyclobutyl, 2,2,3-trifluoro-3-chlorocyclobutyl, 2,2- dichloro-3,3-difluorocyclobutyl, fluorocyclopentyl, difluorocyclopentyl, chlorocyclopentyl, perfluorocyclopentyl, chlorocyclohexyl and pentachlorocyclohexyl.

Alkylthio is, for example, methylthio, ethylthio, propylthio or butylthio or a branched isomer thereof.

Phenyl per se, or as part of a substituent, such as, for example, phenylthio or benzoyloxy, may be unsubstituted or substituted, in which case the substituents may be in the ortho-, meta- or para-position. Unless specifically indicated, substituents are, for example, C1-C4- alkyl, C1-C4alkoxy, halogen or C1 -C4haloalkyl.

Corresponding meanings may also be given to the substituents in combined definitions, such as, for example, alkyl-S(O)-, alkyl-ON=CH-, (alkyl)2NCO-, alkenyl-SO-, alkynyl-S(O)n2-, alkylcarbonyloxy-, haloalkoxycarbonyl-, haloalkyl-S(0)20-, haloalkyl-SO-, (alkyl)2NS(0)2-, alkyl-S(0)20-, alkyl substituted by unsubstituted or R17-substituted phenyl, alkenyl substituted by unsubstituted or R,7-substituted phenyl, alkyl-S(0)2NH-, haloalkyl-S(O)2NH-, alkylNHS(O)2-, alkylNHCO-, haloalkylNHCO-, (alkyl)2NCS-, H(alkoxy)P(O)O-, alkyl(alkoxy)P(O)O-, (alkoxy)2P(O)O-, alkoxycarbonyl-alkenyl, alkyl-S(O)2 substituted by unsubstituted or R17-substituted phenyl, alkoxy-alkyl-S(O)n2- and alkynyl-S(O)n2-.

In the definitions of cyanoalkyl, alkylcarbonyl, alkoxycarbonylalkenyl, alkylcarbonyloxy, alkoxycarbonyl, alkoxycarbonyloxy and haloalkoxycarbonyl, the upper and lower limits of the number of carbon atoms given in each case do not include the cyano or carbonyl carbon atom, as the case may be.

The compounds of formula I wherein Q is a group Q, to Q4 and Ra is OH can be in the form of mixtures of the following isomeric forms Ii to 14 and Ic: In the above isomeric compounds of formulae I1 to 14 and Ic: when Z1 = C(R6)R7, Z2 = (W)n6, Z3 = C(R6)R7 and n4 = 0, the right-hand portion of the isomeric compounds represents the group Q1; when Z1 = CH, Z2 = O, S or -(CH2)n5-, Z3 = CH and n4 = 2, the right-hand portion of the isomeric compounds represents the group Q2; when Z1 = CH2, Z2 = CHNHR9, Zs = CH2 and n4 = 0, the right-hand portion of the isomeric compounds represents the group Q3; or when Z1 = NR10, Z2 = 0, Z3 = C(R6)R7 and n4 = 0, the right-hand portion of the isomeric compounds represents the group Q4.

The compounds of formula I wherein Q is a group Qs may also be in the form of mixtures of the following isomeric forms I6, I7 and le: The invention includes all those isomeric forms Ii to 14, Ic, 16, 17 and le and their mixtures 11 to i4 and Ic, and 16,17 and le.

The invention likewise includes the salts that the compounds of formula I having azide hydrogen, for example the compounds of formulae 13 and 16 and the derivatives having carboxylic acid and sulfonamide groups (e.g. carboxy-substituted phenyl, alkyl-S(0)2NH and haloalkyl-S(O)2NH groups) are able to form with bases. Those salts are, for example, alkali metal salts, e.g. sodium and potassium salts; alkaline earth metal salts, e.g. calcium and magnesium salts; ammonium salts, that is to say unsubstituted ammonium salts and mono- or poly-substituted ammonium salts, e.g. triethylammonium and methylammonium salts; or salts with other organic bases.

Among the alkali metal and alkaline earth metal hydroxides as salt formers, attention is drawn, for example, to the hydroxides of lithium, sodium, potassium, magnesium and calcium, but especially to the hydroxides of sodium and potassium. Suitable salt formers are described, for example, in WO 97/41112.

Among the alkali metal and alkaline earth metal hydrides attention is drawn, for example, to sodium hydride and calcium hydride, and among the carbonates attention is drawn to the carbonates of sodium, potassium, caesium, calcium, barium, magnesium and lithium.

Examples of amines suitable for ammonium salt formation include ammonia as well as primary, secondary and tertiary C,-C18alkylamines, C1 -C4hydroxyalkylamines and C2-C4- alkoxyalkylamines, for example methylamine, ethylamine, n-propylamine, isopropylamine, the four isomers of butylamine, n-amylamine, isoamylamine, hexylamine, heptylamine, octylamine, nonylamine, decylamine, pentadecylamine, hexadecylamine, heptadecylamine, octadecylamine, methylethylamine, methylisopropyiamine, methylhexylamine, methylnonyl- amine, methylpentadecylamine, methyloctadecylamine, ethylbutylamine, ethylheptylamine, ethyloctylamine, hexylheptylamine, hexyloctylamine, dimethylamine, diethylamine, di-n- propylamine, diisopropylamine, di-n-butylamine, di-n-amylamine, diisoamylamine, dihexylamine, diheptylamine, dioctylamine, ethanolamine, n-propanolamine, isopropanol- amine, N,N-diethanolamine, N-ethylpropanolamine, N-butylethanolamine, allylamine, n-butenyl-2-amine, n-pentenyl-2-amine, 2,3-dimethylbutenyl-2-amine, dibutenyl-2-amine, n-hexenyl-2-amine, propyienediamine, trimethylamine, triethylamine, tri-n-propylamine, triisopropylamine, tri-n-butylamine, triisobutylamine, tri-sec-butylamine, tri-n-amylamine, methoxyethylamine and ethoxyethylamine; heterocyclic amines, for example pyridine, quinoline, isoquinoline, morpholine, thiomorpholine, piperidine, pyrrolidine, indoline, quinuclidine and azepine; primary arylamines, for example anilines, methoxyanilines, ethoxyanilines, o-, m- and p-toluidines, phenylenediamines, benzidines, naphthylamines and o-, m- and p-chloroanilines; but especially triethylamine, isopropylamine and diisopropylamine.

The salts of compounds of formula I having basic groups, especially having basic amino groups, for example alkylamino and dialkylamino groups, in the definition of R6, R7 or R17 are, for example, salts with inorganic or organic acids, for example hydrohalic acids, such as hydrofluoric acid, hydrochloric acid, hydrobromic acid or hydriodic acid, and also sulfuric acid, phosphoric acid, nitric acid, and organic acids, such as acetic acid, trifluoroacetic acid, trichloroacetic acid, propionic acid, glycolic acid, thiocyanic acid, citric acid, benzoic acid, oxalic acid, formic acid, benzenesulfonic acid, p-toluenesulfonic acid and methanesulfonic acid.

The possibility of the presence of at least one asymmetrical carbon atom in the compounds of formula I, for example in the substituent R1, where R1 is a branched alkyl, alkenyl, halo- alkyl or alkoxyalkyl group, or where R1 and R2 and/or R3 and R4, and R6 and R7 are different from one another, means that the compounds may occur in the form of optically active single isomers or in the form of racemic mixtures.

Because rotation between the benzoyl and the Q1 to Q6 ring systems is hindered, the com- pounds of formula I may also be in the form of rotational isomers (atropisomers).

In the present invention, "compounds of formula I" is to be understood as including both the pure optical antipodes and the racemates or diastereoisomers and atropisomers.

When an aliphatic C=C or C=N-O double bond (syn/anti) is present, geometric isomerism may occur. The present invention relates to those isomers also.

Preference is given to compounds of formula I wherein R1 is C1-C4alkyl, C1-C4haloalkyl, C1 -C4alkoxy-C1-C4alkyl, C1 -C4alkoxycarbonyl, cyano, cyano-C1-C4alkyl, CHO, C1-C4alkyl- ON=CH, C2-C6alkenyl, C1-C4alkoxycarbonyl-C2-C6alkenyl or a group CH(OR20)0R2, W is oxygen, sulfur, -C(R,8)2- or -N(R22)-; each Ria independently of the other is hydrogen, C1-C4alkyl or C1-C4alkoxycarbonyl; and R22 is hydrogen, C1-C4alkyl or C1-C4alkoxycarbonyl.

Also preferred are compounds of formula I wherein Q is a group R6 and R7 are each independently of the other C1-C4alkyl or C,-C4alkyl-S(O)n2; n2 is 0; R8 is OH, C1-C4alkoxy, C1-C4alkylcarbonyloxy, phenylthio or C1-C4alkylthio; Rio, R11 and R12 are each independently of the others hydrogen, C1-C4alkyl or C,-C4alkoxycarbonyl; R13 is halogen, C,-C4alkyl, C3-C6- cycloalkyl, COOR16, COR15 or cyano; R14 is C1-C4alkyl, C3-C6alkynyl, C3-C6cycloalkyl or C3-C6cycloalkyl substituted by halogen, C1-C4alkyl, C1-C4haloalkyl, C3-C6alkenyl, C3-C6halo- alkenyl, C3-C6alkynyl, C3-C6haloalkynyl or phenyl; R15 is C1-C4alkyl, C1-C4haloalkyl, C3-C6- alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl or phenyl; and R16 and Y are as defined for formula I.

Also preferred are compounds of formula I wherein Q is a group R6 and R7 are each independently of the other C1-C4alkyl or C1-C4alkyl-S(O)n2; n2 is 0; Ra is OH, C1-C4alkoxy, C1-C4alkylcarbonyloxy, phenylthio or C1-C4alkylthio; W is oxygen or -C(Ria)2-; Ria is hydrogen; n6 is 1; and Rg is (C1-C4alkyl)- NHCO or (C1-C4alkyl)2NCO.

Preference is given also to compounds of formula I wherein n is 1 or 2.

The process according to the invention for the preparation of compounds of formula I wherein R1 to R5 and n are as defined for formula I; Q is a group R7, R9, R10, W, n6 and Y are as defined for formula I is carried out analogously to known procedures and comprises either a) reacting a compound of formula Ill wherein R1 to R5 and n are as defined and X is a leaving group, e.g. halogen, in an inert organic solvent in the presence of a base with a compound of formula IV wherein Z1 is C(R6)R7, Z2 is (W)n6, Z3 is C(R6)R7 and n4 is O (= group Q1); Z1 is CH, Z2 is oxygen, sulfur or -(CH2)n5- (=Y), Z3 is CH and n4 is 2 (= group Q2); Z1 is CH2, Z2 is CHNHR9, Z3 is CH2 and n4 is O (= group Q3); or Z1 is NR10, Z2 is oxygen, Z3 is C(R6)R7 and n4 is O (= group Q4), and R6, R7, R9, R10, W, n6 and n5 are as defined for formula I, to form a compound of formula Ic and then isomerising that compound, for example in the presence of a base and a catalytic amount of a cyanide source; or b) reacting a compound of formula Id wherein R1 to R5 and n are as defined, with a compound of formula IV wherein Z1, Z2, Z and n4 are as defined, in an inert organic solvent in the presence of a base and a coupling agent to form a compound of formula Ic and then isomerising that compound, for example as described under Route a).

The process according to the invention for the preparation of compounds of formula I wherein R1 to R5 and n are as defined for formula I; Q is a group R11 and R12 are as defined for formula I is carried out analogously to known procedures and comprises either: a) reacting a compound of formula Ill wherein R1 to R5 and n are as defined and X is a leaving group, e.g. halogen, with a compound of formula IVa wherein R11 and R12 are as defined, in an inert organic solvent in the presence of a base to form a compound of formula le and then isomerising that compound, for example in the presence of a base and a catalytic amount of a cyanide source; or b) reacting a compound of formula Id wherein R1 to R5 and n are as defined, with a compound of formula IVa wherein R11 and R12 are as defined, in an inert organic solvent in the presence of a base and a coupling agent to form a compound of formula le and then isomerising that compound as described under Route a).

The process according to the invention for the preparation of compounds of formula I wherein R1 to R5 and n are as defined for formula I; Q is a group hydrogen, C1-C4alkyl, C1-C4alkyl substituted by unsubstituted or R17-substituted phenyl, C1 -C4haloalkyl, C2-C6alkenyl, C2-C6alkenyl substituted by unsubstituted or R17-substituted phenyl, C2-C6alkynyl, C2-C6alkynyl substituted by unsubstituted or R17-substituted phenyl, C3-C6haloalkenyl, C3-C6haloalkynyl, C3-C6cycloalkyl, C3-C6cycloalkyl substituted by halogen, R15 or COOR16; C1-C4alkyl-S(O)n2, C,-C4alkyl-S(O)n2 substituted by unsubstituted or R17- substituted phenyl, C1-C4alkoxy-C2-C6alkyl-S(O)n2, C2-C6alkenyl-S(O)n2, C2-C6alkenyl-S(O)n2 substituted by unsubstituted or R17-substituted phenyl, C2-C6alkynyl-S(O)n2 or C2-C6alkynyl- S(O)n2 substituted by unsubstituted or R17-substituted phenyl; and R14 to R17 and n2 are as defined for formula I, is carried out analogously to known procedures and comprises either: a) converting a compound of formula V wherein R1 to R5, R14 and n are as defined, in the presence of a base, carbon disulfide and an alkylating reagent of formula VI R25-X1 (VI), wherein R25 is C1-C4alkyl, C1-C4alkyl substituted by unsubstituted or R,7-substituted phenyl, C1-C4alkoxy-C2-C6alkyl, C2-C6alkenyl, C2-C6alkenyl substituted by unsubstituted or R17- substituted phenyl, C2-C6alkynyl or C2-C6alkynyl substituted by unsubstituted or R17- substituted phenyl; R17 is as defined for formula I, and X1 is a leaving group, e.g. halogen or sulfonate, into a compound of formula VII wherein R1 to R5, R14, R25 and n are as defined, then cyclising that compound with hydroxyl- amine hydrochloride, optionally in a solvent, in the presence of a base to form a compound of formula If wherein R1 to R5, R14 and n are as defined, R13 is R25S and R25 is C1-C4alkyl, C1-C4alkyl substituted by unsubstituted or R17-substituted phenyl, C1-C4alkoxy-C2-C6alkyl, C2-C6alkenyl, C2-C6alkenyl substituted by unsubstituted or R,7-substituted phenyl, C2-C6alkynyl or C2-C6- alkynyl substituted by unsubstituted or R17-substituted phenyl, and then oxidising that com- pound, for example with meta-chloroperbenzoic acid (m-CPBA); or b) converting a compound of formula V wherein R1 to R5, R14 and n are as defined, with an orthoacid amide of formula VIII wherein R13 is hydrogen, C1-C4alkyl, C1-C4alkyl substituted by unsubstituted or R17- substituted phenyl, C1-C4haloalkyl, C2-C6alkenyl, C2-C6alkenyl substituted by unsubstituted or R,7-substituted phenyl, C2-C6alkynyl, C2-C6alkynyl substituted by unsubstituted or R17- substituted phenyl, C3-C6haloalkenyl, C3-C6haloalkynyl, C3-C6cycloalkyl or C3-C6cycloalkyl substituted by halogen, R15 or COOR16; R15 to R17 are as defined for formula I; and R26 and R27 are each independently of the other C1-C4alkyl, into a compound of formula IX wherein R1 to R5, R13, R14, n and R27 are as defined, and then cyclising that compound in the presence of hydroxylamine hydrochloride, optionally in a solvent, in the presence of a base to form a compound of formula If The process according to the invention for the preparation of compounds of formula Id wherein R1, R3 to R5 and n are as defined for formula I and R2 is CH3 is carried out analogously to known procedures and comprises either: a) etherifying a compound of formula XX wherein R5 is as defined for formula I and R28 is C1-C4alkyl, with a compound of formula XXV wherein R1, R3 and R4 are as defined for formula I and Hal is halogen, to form a compound of formula XXI wherein R1, R3 to R5 and R28 are as defined, subjecting that compound to a Claisen rearrangement and then acylating the resulting compound of formula XXII with a compound of formula XXVI S II Hal-C-N(C1-O4aIkyl)2 (XXVI), wherein Hal is chlorine, bromine or iodine, to yield a compound of formula XXIII N(C1-C4alkyI)2 H2C>z R1 / 0 0 R II 3 I R R, OR, which is subjected to a rearrangement and yields a compound of formula XXIV N(C1-C4alkyl)2 H2C R1 S 0 II R3 COR (XXIV), R4$ 28 OR, R5 then hydrolysing and cyclising that compound to form a compound of formula Id wherein R, and R3 to R5 are as defined, R2 is CH3 and n is 0, and then oxidising that compound (n is 1 or 2); or b) first brominating a compound of formula XX wherein R5 and R28 are as defined, to yield a compound of formula XXb subjecting that compound to a coupling reaction in the presence of a catalyst and an organometal reagent of formula XXVb wherein R1, R3 and R4 are as defined and R29 is C1-C4alkyl, to yield a compound of formula XXII wherein RI, R3 to R5 and R28 are as defined, and reacting that compound further analogously to the method described under Route a) to form a compound of formula Id. The process according to the invention for the preparation of compounds of formula Id wherein R1, R3 to R5 and n are as defined for formula I and R2 is CH3 is carried out analogously to known procedures and comprises reacting a compound of formula XXa wherein R5 is as defined and R28 is C1-C4alkyl, with a compound of formula XXVa wherein R1, R3 and R4 are as defined, to yield a compound of formula XXla subjecting that compound to a Claisen rearrangment to yield a compound of formula XXlla which is then hydrolysed and cyclised to form a compound of formula Id wherein R, and R3 to R5 are as defined, R2 is CH3 and n is 0, and then oxidising that compound (n is 1 or 2).

The process according to the invention for the preparation of compounds of formula I wherein R1 to R5 and n are as defined for formula I and Q is halogen is carried out analogously to known procedures and comprises treating a compound of formula Id wherein R1 to R5 and n are as defined, with a halogenating agent.

The preparation of the compounds of formula I is illustrated in more detail in the following Reaction Schemes 1 to 6.

Reaction Scheme 1 Route a): R R2 0 R3 RCOCX t IZ3 base z2\ d R5 HO Z1 (CH2)n 0-110°C Ill it R R1 0 isomerisation: S(O), O\0 0) 0 Z3 base e.g. ( (CH,),, R 3R2S(n0ii z2 KCNcat. 4 z3 \fs ° e.g. (C,H,),N,~ Z R4$iO Z1>(CH2) R5 Ic I (R8=OH) Route b): R XS(O) O O R3>l \ R3 R Iz2\ base e.g. (C2H5)3N, coupling 4$1OH + reagent e.g. R5 (CH2)n Id HOZiv 4 CH3 solvent e.g. CH3CN, 0-110"C O R R1 R2 / )t isomerisation: R yLS(O)n R R: 0 base e.g. (C2H5)3N, 3 C R, KON z3 R, "' ° (CH2)¼ cat. 4Nz'2\ R5 R8 Zi(CH2) R5 Ic I (R6=OH) n4 ic I (R8 = OH) In Reaction Scheme 1 when Z1 = C(R6)R7, Z2 = (W)n6, Z3 = C(R6)R7 and n4 = 0, the right-hand portion of the compounds of formula I represents the group Q1; when Z1 = CH, Z2 = O, S or -(CH2)ns-, Z3 = CH and n4 = 2, the right-hand portion of the compounds of formula I represents the group Q2; when Z1 = CH2, Z2 = CHNHRg, Z3 = CH2 and n4 = 0, the right-hand portion of the compounds of formula I represents the group Q3; or when Z1 = NRro, Z2 = 0, Z3 = C(R6)R7 and n4 = 0, the right-hand portion of the compounds of formula I represents the group Q4.

Reaction Scheme 2 Route a): R1 R2\1 0 R12 R3 n ii R ( X HO N base e.g. (C2H5)3N, solvent e.g. CH3CN, 5 R,1 0-110°C III IVa R R12 S(O), R2 is0 0) 0 isomerisation: R3 ng R11 R2t R1\2 base e.g. (02H5)3N, n 1°l R4$1O 4s KON cat , N R5 R12 le I (Q=Q5) Route b): P' R12 R4,CsOH II base R, + HO \OH e.g. OH 44 base e.g. (C2H5)3N, coupling R5 R11 I Id IVa I- CH3 OH3 solvent, e.g. CH3CN, 0-110"C R2R500 R2 R1 R2 R t o R12 isomerisation: R 5(0)n0 R R,.7( base e.g. (O2H3N, 3 CX N,N KONcat. R4$IIN\)N R11 R5 HO R5 R12 le I (Q=Q5) Reaction Scheme 3 Route a): R 2R150 R2 5(0) 0 R K2CO3/CS2 R,,-X,, R2 0 R3 II n0110i C C VI R3 R 3X3 solvent e.g. DMF, or R4$1CIIB14 R, KFIAIIO52, R,,-X, R5 RISO VI R, ,S 'SR solvent e.g. CH3CN, or Is NaH/CS2. R2çX19 solvent e.g. DMSO Vll R R2 0 P13 NH20H HCI, base e.g. R3tC0 [O] e.g. m-CPBA R IN NaOAc/01H50H R5 R14 If (R13=R2ss-) R2 R1 R fl 13 RaRCI\N , RX If (Rr3=R2sSO- or R2sS°2-) Route b): 0 R, R26OX O R, RCIOl ,°, R26O' 0 R 27)2 WCsc'csR n II 26 R13 R3 oII II 321(O)C C, OH2 R14 VIII R C R14 R41 - 11 II ~~~~ C -- Rs Rs R13 N(R27)2 V IX R R2 NH2OH. HCI, base e.g. 7W 1°l R13 NaOAc/C2HsOH OH XoN 14 If For the preparation of compounds of formula I wherein Q is a group Q1 to Q4 and Re is OH, according to Reaction Scheme 1, Route a), the starting materials used are carboxylic acid derivatives of formula Ill wherein X is a leaving group, e.g. halogen, for example iodine, bromine or especially chlorine, N-oxyphthalimide or N,O-dimethylhydroxylamino or part of an activated ester, e.g.

(formed from dicyclohexylcarbodiimide (DCC) and the corresponding carboxylic acid) or (formed from N-ethyl-N'-(3-dimethylaminopropyl)-carbodiimide (EDC) and the corresponding carboxylic acid). Those starting materials are reacted in an inert organic solvent, for example a halogenated hydrocarbon, e.g. dichloromethane, a nitrile, e.g. acetonitrile, or an aromatic hydrocarbon, e.g. toluene, and in the presence of a base, for example an alkylamine, e.g. triethylamine, an aromatic amine, e.g. pyridine or 4-dimethylaminopyridine (DMAP), with a dione derivative of formula IV to form isomeric enol ethers of formula Ic. The esterification takes place at temperatures of from 0°C to 11 0°C.

The isomerisation of the ester derivatives of formula Ic to form the dione derivatives of formula I (Ra = OH) can be carried out, for example, analogously to EP-A-O 369 803 in the presence of a base, for example an alkylamine, e.g. triethylamine, or a carbonate, e.g. potassium carbonate, and a catalytic amount of a cyanide source, for example acetone cyanohydrin or potassium cyanide.

According to Reaction Scheme 1, Route b), the desired diones of formula I (R8 = OH) can be obtained, for example, analogously to Chem. Lett. 1975, 1045 by esterification of the carboxylic acids of formula Id with the dione derivatives of formula IV in an inert solvent, for example a halogenated hydrocarbon, e.g. dichloromethane, a nitrile, e.g. acetonitrile, or an aromatic hydrocarbon, e.g. toluene, in the presence of a base, for example an alkylamine, e.g. triethylamine, and a coupling agent, for example 2-chloro-1 -methyl-pyridinium iodide.

The esterification is carried out, depending upon the solvent used, at temperatures of from 0°C to 110"C and yields first, as described under Route a), the isomeric ester of formula Ic, which can be isomerised as described under Route a), for example in the presence of a base and a catalytic amount of a cyanide source, to form the desired dione derivative of formula I (Ra = OH).

According to Reaction Scheme 2, the compounds of formula I wherein Q is a group Q5 can be obtained in a manner analogous to that described, for example, in Reaction Scheme 1 or Tetrahedron 36, 2409 (1976), either a) by esterification of a carboxylic acid derivative of formula Ill with the hydroxypyrazole derivative of formula IVa in an inert organic solvent and in the presence of a base, or b) by esterification of the carboxylic acid of formula Id with the hydroxypyrazole derivative of formula IVa in an inert solvent in the presence of a base and a coupling agent, and subse- quent isomerisation of the intermediately formed ester of formula le, for example with the aid of a base and a catalytic amount of cyanide source.

The preparation of the compounds of formula I wherein Q is the group Q6 can be carried out in accordance with Reaction Scheme 3 advantageously either via Route a) by reacting the -diketone derivative of formula V, e.g. analogously to Synthesis 1991, 301; ibid. 1988, 793; or Tetrahedron 32, 3055 (1976), with carbon disulfide in the presence of a base, for example a carbonate, e.g. potassium carbonate, a metal hydride, e.g. sodium hydride, or potassium fluoride on aluminium, and an alkylating reagent of formula VI wherein X1 is a leaving group, e.g. halogen, for example iodine, bromine or especially chlorine, R250SO20-, CH3SO20- or The reaction is advantageously carried out in a solvent, for example an amide, e.g. N,N-dimethylformamide (DMF), a sulfoxide, e.g. dimethyl sulfoxide (DMSO), or a nitrile, e.g. acetonitrile. The resulting ketene thioacetal of formula VII is cyclised with the aid of hydroxylamine hydrochloride in the presence of a base, for example sodium acetate, in a solvent, for example an alcohol, e.g. ethanol, or an ether, for example tetrahydrofuran, to form a compound of formula If wherein R13 is R25S-. The cyclisation reaction is advantageously carried out at temperatures of from 0°C to 100"C. If desired, the compound of formula If can be oxidised analogously to known standard procedures, e.g. with peracids, for example meta-chloroperbenzoic acid (m-CPBA) or peracetic acid, to form the corresponding sulfone or sulfoxide of formula If (R13 = R25SO- or R25SO2-); or can be carried out via Route b), by converting the -diketone derivative of formula V analogously to J. Het.

Chem. 20, 645 (1983) with an orthoacid amide of formula VIII, for example dimethylformamide dimethyl acetal, into the enamine derivative of formula IX and then cyclising that derivative with the aid of hydroxylamine hydrochloride, in the presence of a base, e.g. sodium acetate, in a solvent, for example an alcohol, e.g. ethanol, to form a compound of formula If.

The preparation of the 4-benzoylisoxazole derivatives of formula I (Q=Q6) wherein Rt3 is COOT,6, COR15, cyano, nitro or CONH2 can also be carried out, for example, analogously to WO 96/21357 and references cited therein.

The carboxylic acids of formula Id can be prepared analogously to known procedures, e.g. in accordance with the methods given in Reaction Schemes 4 and 5 below.

Reaction Scheme 4 Route a) OH 0 R CH1 OH Ol /C o C s 3 OR28 alkenylation: R4 R1 R5 /> II8 R3 R11 OR18 XX R ,C=CCH2-Hai R5 XXI XXV N(C1-C4aIkyI)1 cRlo R H1 H 0 H1C1 ' 0 H2C 1 </ acylation e.g. H2C O ° Claisen rearrangement R3 acylation e.g. RX CsOR T A S R41 R5 Hal-K' R5 5 N(C1-c4aikyl)2 Rs XXII XXVI XXIII N/C,-C4alkYl)2 c=o R H1 0 R2 rearrangement 3Ri{ 1) hydrolysis ts\(o)n R II '5(0)n?1 ~~~~~~~~~~~~ R,- OR 3 T, solvent R4I 18 2) cyclisation R Rs R XXIV Id (R2=CH3; n= 0) R R2 t Rt8xoH I e.g. R3 R OH m-CPBA - solvent, R o.llooc Id (R2=CH3; n= 1 or 2) Route b): OH 0 OH 0 OR28 bromination: Br2 BrgCsoR lexis acid, solvent, 0R28 R5 O-1000C R5 XX XXb R H2C OH O coupling < , R1R3 R,-R,rC ~~~~~ Id R, R, R3 II Pd[(C8H5)3P]4 R41 - CH1=C-C ) Pd[(C6Hs)3P]4 R4 R5 XXVb XXII solvent, 0-200"C Reaction Scheme 5 R3 Br OS 0 Br Cs aromat. nucleophilic R 4S 0 substitution e.g. R, z OR R, R3 R11 ---* IS ~~~ XXa C=C-CH1SH, solvent, R4 XXVa XXla base, 0-200°C 1cRi R, S(O), R1 H SH 0 B1 S(O)O II R3 nII Claisen rearrangement R3 OR28 1) hydrolysis Rt;,8soH T 4 Id (R, =CH,; n=O) Rs </ 2) cyclisation Rs 9/ ~ XXlla Id (R2 =CH3; n=o) R B1 1S(O)O R flclI [O] e.g. b R4 \ OH m-CPBA Id (R2=CH3; n= 1 or 2 ) The alkenylation of the salicylic acid derivative of formula XX wherein R28 is C1-C4alkyl in accordance with Route a) in Reaction Scheme 4 is carried out, for example, analogously to standard etherification methods by means of reaction with an allyl halide of formula XXV wherein Hal is halogen, especially chlorine, bromine or iodine, in an aprotic solvent, for example an amide, e.g. N,N-dimethylformamide (DMF) or 1 -methyl-2-pyrrolidone (NMP), a sulfoxide, e.g. dimethyl sulfoxide (DMSO), a ketone, e.g. acetone, or a nitrile, e.g. aceto- nitrile, in the presence of a base, for example a carbonate, e.g. potassium or caesium carbonate, or a metal hydride, e.g. sodium hydride. The reaction temperatures are generally in the range of from 0CC to 110"C.

The subsequent Claisen rearrangement of the allyl ether of formula XXI in Reaction Scheme 4 can be carried out, for example, thermally at temperatures of from 100"C to 300"C, optionally in an inert solvent, for example an aromatic hydrocarbon, e.g. xylene.

Alternatively the thermal Claisen rearrangement can be carried out, for example, also without a solvent in a microwave oven. Such Claisen rearrangements are described, for example, in C. Ferri, "Reaktionen der organischen Synthese", Georg Thieme Verlag, Stuttgart, 1978, page 461 ff..

In accordance with Reaction Scheme 4, the resulting phenol derivative of formula XXII is then acylated, for example with a thiocarbamoyl halide of formula XXVI, e.g. N,N-dimethyl- thioformyl chloride, in an aprotic solvent, for example an amide, e.g. N,N-dimethylformamide (DMF) or 1-methyl-2-pyrrolidone (NMP), a sulfoxide, e.g. dimethyl sulfoxide (DMSO), a ketone, e.g. acetone, or a nitrile, e.g, acetonitrile, in the presence of a base, for example a carbonate, e.g. potassium or caesium carbonate, or a metal hydride, e.g. sodium hydride.

The acylation is advantageously carried out at temperatures of from 0°C to 110"C.

The rearrangement of the thiocarbamate of formula XXIII in Reaction Scheme 4 is effected, for example, thermally in an inert solvent, for example an ether, e.g. diphenyl ether, at temperatures of from 100°C to 300"C and yields the thiolcarbamate of formula XXIV. That compound is then hydrolysed and cyclised using base or acid catalysis to form a compound of formula Id wherein R2 = CH3 and n = 0. This is effected advantageously either with a metal hydroxide, e.g. sodium hydroxide, or with a mineral acid, e.g. hydrochloric acid or sulfuric acid, at temperatures of from 0°C to 110"C. Suitable solvents are, for example, water, ethers, e.g. tetrahydrofuran, halogenated hydrocarbons, e.g. dichloromethane, and aromatic hydrocarbons, e.g. toluene.

The resulting benzothiophene derivative of formula Id wherein R2 is methyl and n is 0 can then be oxidised in accordance with various standard methods. Advantageously the oxidation is carried out, for example, with hydrogen peroxide in an acidic solvent, for example an organic acid, e.g. acetic acid, or with an organic peracid, for example meta- chloroperbenzoic acid (m-CPBA), in an inert solvent, for example a halogenated hydro- carbon, e.g. dichloromethane, or an aromatic hydrocarbon, e.g. toluene. The reaction temperatures for the oxidation are generally in the range of from 0°C to 110"C. The degree of oxidation at the sulfur atom (n = 1 or 2) can be controlled by the amount of oxidising agent.

The above reaction sequence via acylation of the phenol derivative of formula XXII to form a thiocarbamate of formula XXIII, rearrangement of the latter compound to form a thiol- carbamate of formula XXIV and hydrolysis and cyclisation to form a compound of formula Id (n = 0) is carried out, for example, analogously to Org. Synth. 51,139 (1971), and the oxidation to form a compound of formula Id (n = 1 or 2) is carried out, for example, as described in H. O. House, "Modern Synthetic Reactions" W. A. Benjamin, Inc., Menlo Park, California, 1972, pages 334-335 and 353-354.

The electrophilic bromination according to Route b) in Reaction Scheme 4 is carried out, for example, analogously to Chem. Communic. 1972, 214. The bromination of the salicylic acid derivative of formula XX can be effected, for example, in an inert solvent, for example a halogenated hydrocarbon, e.g. dichloromethane, and in the presence of a Lewis acid, for example titanium halide, e.g. titanium tetrachloride, at temperatures of from 0°C to 100°C.

The subsequent coupling of the resulting bromosalicylic acid derivative of formula XXb to a trialkyltin-olefin of formula XXVb wherein R29 is C1-C4alkyl is carried out analogously to Angew. Chem. 98, 504 (1986) in an organic solvent, for example an ether, e.g. tetrahydro- furan, an aromatic hydrocarbon, e.g. toluene, and in the presence a palladium catalyst, for example tetrakis(triphenylphosphine)palladium. The reaction temperature is advantageously from 0°C to 200"C. The coupling product of formula XXII obtained by Route b) can then, for example in a manner analogous to that described under Route a), be acylated, rearranged, hydrolysed and cyclised, and optionally oxidised to form a compound of formula Id.

The aromatic nucleophilic substitution of the ortho-bromobenzoic acid ester of formula XXa wherein R28 is C1-C4alkyl in Reaction Scheme 5 can be carried out analogously to known procedures, as described, for example, in J. March, "Advanced Organic Chemistry", 4th Edition, John Wiley & Sons, New York, 1992, pages 641-676. Accordingly, the benzoic acid ester of formula XXa is reacted with an alkenyl sulfide of formula XXVa in an aprotic solvent, for example an amide, e.g. N,N-dimethylformamide (DMF) or 1-methyl-2- pyrrolidone (NMP), a sulfoxide, e.g. dimethyl sulfoxide (DMSO), a ketone, e.g. acetone, or a nitrile, e.g. acetonitrile, in the presence of a base, for example a carbonate, e.g. potassium or caesium carbonate, or a metal hydride, e.g. sodium hydride, at temperatures of from 0°C to 200"C.

The subsequent Claisen rearrangement of the resulting thioallyl ether of formula XXla in Reaction Scheme 5 can advantageously be carried out in a manner analogous to that described in J. Org. Chem. USSR 13, 2437 (1977) and under Reaction Scheme 4 for the allyl ether of formula XXI, at temperatures of from 100"C to 300"C. The subsequent hydro- lysis and cyclisation of the thiophenol of formula XXlla and the optional oxidation of the resulting dihydrobenzo[b]thiophene derivative of formula Id (n=0) are advantageously like- wise carried out as already described under Reaction Scheme 4.

The activated carboxylic acid derivatives of formulae Ill and I in Reaction Schemes 1 and 2 (Route a)) wherein X is a leaving group, for example halogen, e.g. bromine, iodine or espe- cially chlorine, can be prepared according to known standard procedures as described, for example, by C. Ferri in "Reaktionen der organischen Synthese", Georg Thieme Verlag, Stuttgart, 1978, page 461 ff., such as, for example, in accordance with Reaction Scheme 6 below.

Reaction Scheme 6 In accordance with Reaction Scheme 6, the preparation of the compounds of formula Ill (X = leaving group) and I (X = halogen) is carried out, for example, advantageously by the use of a halogenating agent, for example a thionyl halide, e.g. thionyl chloride or bromide; a phosphorus halide or phosphorus oxyhalide, e.g. phosphorus pentachloride or phosphorus oxychloride, or phosphorus pentabromide or phosphoryl bromide; or an oxalyl halide, e.g. oxalyl chloride, or by the use of a reagent for forming activated esters, for example N,N'- dicyclohexylcarbodiimide (DCC) or N-ethyl-N'-(3-dimethylaminopropyl)-carbodiimide (EDC) of formula X. Where the compound of formula X is a halogenating agent, the group X is, for example, a leaving group, for example halogen, e.g. fluorine, bromine or iodine or especially chlorine, and W1 is, for example, PC12, SOCI, SOBr or CICOCO.

The operation is optionally carried out in an inert organic solvent, for example in an aliphatic, halogenated aliphatic, aromatic or halogenated aromatic hydrocarbon, for example n-hexane, benzene, toluene, a xylene, dichloromethane, 1 ,2-dichloroethane or chlorobenzene, at reaction temperatures in the range of from -20°C to the reflux temperature of the reaction mixture, preferably at from 40 to 150"C, and in the presence of a catalytic amount of N,N-dimethylformamide. Such reactions are known and various variations thereof in respect of the leaving group X are described in the literature.

The compounds of formulae V, VII and IX (Reaction Scheme 3) are novel. They are import- ant intermediates for the synthesis of the compounds of formula If. The invention therefore relates also to those compounds.

The compounds of formula IV (Reaction Scheme 1) wherein Z1 = C(R6)R7, Z2 = (W)n6, Z3 = C(R6)R7 and n4 = 0 are known and can be prepared in a manner analogous to that described, for example, in US-A-5 006 150, WO 97/08164, DE-OS-3 818958 and DE-OS-3 902 818.

The compounds of formula IV (Reaction Scheme 1) wherein Z1 = CH, Z2 = O, S or -(CH2)n5-, Z3 = CH and n4 = 2 are known and can be prepared in a manner analogous to that described, for example, in EP-A-0 338 992.

The compounds of formula IV (Reaction Scheme 1) wherein Z1 = CH2, Z2 = CHNHRg, Z3 = CH2 and n4 = 0 are known and can be prepared in a manner analogous to that described, for example, in EP-A-0 278 907.

The compounds of formula IV (Reaction Scheme 1) wherein Z1 = NR10, Z2 = 0, Z3 = C(R6)R7 and n4 = 0 are known and can be prepared in a manner analogous to that described, for example, in WO 96/26192 and US-A-5 336662.

The compounds of formula IVa (Reaction Scheme 2) wherein R11 and R12 are as defined for formula I are known and can be prepared in a manner analogous to that described, for example, in WO 96/26206 and WO 97/08164.

The compounds of formula V in Reaction Scheme 3 can be obtained in accordance with standard procedures, for example from the corresponding esters of formula XXVI I wherein R1 to R5 and n are as defined for formula I and R28 is C1-C4alkyl, for example via Claisen condensation, or from the compounds of formula III by reaction with a ketocarboxylic acid salt of formula XXVIII wherein R14 is as defined for formula I and M+ is an alkali metal ion (see, for example, WO 96/26192, EP-A-0 496 631).

The salicylic acid derivatives of formula XX (Reaction Scheme 4) are either known (some of them being commercially available, for example when R5 is amino (4-aminosalicylic acid)) or can readily be prepared by standard procedures, for example starting from 4-aminosalicylic acid via diazotisation, Sandmeyer reaction and aromatic, nucleophilic substitution (see e.g.

J. March, "Advanced Organic Chemistry", 4th Edition, John Wiley & Sons, New York, 1992, pages 641-676) or Heck reaction of the resulting halide.

The benzoic acid derivatives of formula XXa (Reaction Scheme 5) are either known or can readily be obtained by bromination of the corresponding benzoic acid derivatives (see Reaction Scheme 4, Route b)).

The reagents of formulae VI, VIII, X, XXV, XXVa, XXVb and XXVI used in Reaction Schemes 3 to 6 are either known or can be prepared analogously to disclosed procedures.

For the preparation of all other compounds of formula I functionalised in accordance with the definitions of R1 and R2 (2-position of the dihydrobenzo[b]thiophene ring), a large number of known standard procedures are available, for example alkylation, halogenation, acylation, amidation, oximation, oxidation and reduction, the choice of a suitable preparation process being governed by the properties (reactivities) of the substituents in the respective intermediates (see e.g. EP-A-0 796 856).

For the preparation of all other compounds of formula I functionalised in accordance with the definition of Ra wherein Q is a group Q1 to Q4, a large number of known standard procedures are available, for example alkylation, acylation and treatment with a sulfur reagent (e.g. P2S5 or Lawesson), the choice of a suitable preparation process being governed by the properties (reactivities) of the substituents in the respective intermediates (see e.g. WO 97/08164 and DE-OS-3 902 818).

All other compounds within the scope of formula I can readily be prepared, taking into account the chemical properties of the dihydrobenzo[b]thiophene or Q moiety in relation to the structure of the dihydrobenzo[b]thiophene or Q rings, in a manner analogous to that described in Preparation Examples P1 to Pi 1 or, for example, to that described in the patent specifications indicated.

The end products of formula I can in conventional manner be isolated by concentration or evaporation of the solvent and purified by recrystallisation or trituration of the solid residue in solvents in which they are not readily soluble, such as ethers, aromatic hydrocarbons or chlorinated hydrocarbons, by distillation or by means of column chromatography and a suitable eluant. The sequence in which it is advantageous to carry out certain reactions in order to avoid possible secondary reactions will also be familiar to the person skilled in the art. Unless the synthesis is specifically aimed at the isolation of pure isomers, the product may be obtained in the form of a mixture of two or more isomers. The isomers can be separated according to methods known per se.

For the use according to the invention of the compounds of formula I, or of compositions comprising them, there come into consideration all methods of application customary in agriculture, for example pre-emergence application, post-emergence application and seed dressing, and also various methods and techniques such as, for example, the controlled release of active ingredient. For that purpose a solution of the active ingredient is applied to mineral granule carriers or polymerised granules (urea/formaldehyde) and dried. If required, it is also possible to apply a coating (coated granules), which allows the active ingredient to be released in metered amounts over a specific period of time.

The compounds of formula I may be used in unmodified form, that is to say as obtained in the synthesis, but they are preferably formulated in customary manner together with the adjuvants conventionally employed in formulation technology, for example into emulsifiable concentrates, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granules or microcapsules. Such formulations are described, for example, on pages 9 to 13 of WO 97/34485. As with the nature of the compositions, the methods of application, such as spraying, atomising, dusting, wetting, scattering or pouring, are chosen in accordance with the intended objectives and the prevailing circumstances.

The formulations, that is to say the compositions, preparations or mixtures comprising the compound (active ingredient) of formula I or at least one compound of formula I and, usually, one or more solid or liquid formulation adjuvants, are prepared in known manner, e.g. by homogeneously mixing and/or grinding the active ingredients with the formulation adjuvants, for example solvents or solid carriers. Surface-active compounds (surfactants) may also be used in addition in the preparation of the formulations. Examples of solvents and solid carriers are given, for example, on page 6 of WO 97/34485.

Depending on the nature of the compound of formula I to be formulated, suitable surface- active compounds are non-ionic, cationic and/or anionic surfactants and surfactant mixtures having good emulsifying, dispersing and wetting properties. Examples of suitable anionic, non-ionic and cationic surfactants are iisted, for example, on pages 7 and 8 of WO 97/34485.

In addition, the surfactants conventionally employed in formulation technology, which are described in, interalia, "McCutcheon's Detergents and Emulsifiers Annual" MC Publishing Corp., Ridgewood New Jersey, 1981, Stache, H., "Tensid-Taschenbuch", Carl Hanser Verlag, MunichNienna 1981, and M. and J. Ash, "Encyclopedia of Surfactants", Vol. I-Ill, Chemical Publishing Co., New York, 1980-81, are also suitable for the preparation of the compositions according to the invention.

The herbicidal formulations generally contain from 0.1 to 99 % by weight, especially from 0.1 to 95 % by weight, of herbicide, from 1 to 99.9 % by weight, especially from 5 to 99.8 % by weight, of a solid or liquid formulation adjuvant, and from 0 to 25 % by weight, especially from 0.1 to 25 % by weight, of a surfactant. Whereas commercial products will preferably be formulated as concentrates, the end user will normally employ dilute formulations. The compositions may also comprise further ingredients, such as stabilisers, for example vege- table oils or epoxidised vegetable oils (epoxidised coconut oil, rape oil or soybean oil), anti- foams, for example silicone oil, preservatives, viscosity regulators, binders, tackifiers, and also fertilisers or other active ingredients.

The compounds of formula I can be used successfully either in the form of a mixture of the isomeric forms Ii to 14 and Ic (Q is a group Q1 to Q4 and Ra is OH) or 16,17 and le (Q is a group Q5) or in the form of pure isomeric forms Ii to 14 or Ic, or 16,17 or le, generally on plants or the locus thereof, at rates of application of from 0.001 to 4 kg/ha, especially from 0.005 to 2 kg/ha. The concentration required to achieve the desired effect can be determined by experiment. It is dependent on the nature of the action, the stage of development of the cultivated plant and of the weed and on the application (place, time, method) and may vary within wide limits as a function of those parameters.

The compounds of formula I are distinguished by herbicidal and growth-inhibiting properties, allowing them to be used in crops of useful plants, especially cereals, cotton, soybeans, sugar beet, sugar cane, plantation crops, rape, maize and rice, and also for non-selective weed control. The term "crops" is to be understood as including also crops that have been made tolerant to herbicides or classes of herbicides as a result of conventional methods of breeding or genetic techniques. The weeds to be controlled may be either monocotyl- edonous or dicotyledonous weeds, such as, for example, Stellaria, Nasturtium, Agrostis, Digitaria, Avena, Setaria, Sinapis, Lolium, Solanum, Phaseolus, Echinochloa, Scirpus, Monochoria, Sagittaria, Bromus, Alopecurus, Sorghum halepense, Rottboellia, Cyperus, Abutilon, Sida, Xanthium, Amaranthus, Chenopodium, Ipomoea, Chrysanthemum, Galium, Viola and Veronica.

The following Examples further illustrate but do not limit the invention.

Preparation Examples: Example P1: 2-Allvloxv-4-chlorobenzoic acid methyl ester 50 g (0.36 mol) of potassium carbonate are added, with stirring, to 56 g (0.3 mol) of 4- chlorosalicylic acid methyl ester in 200 ml of dimethyl sulfoxide. When the slightly exothermic reaction has subsided, 40 g (0.33 mol) of allyl bromide are added dropwise at 25"C. The reaction mixture is stirred at 22"C for 16 hours, poured into water and extracted by shaking with diethyl ether. The combined ether phases are washed with water, dried with sodium sulfate and concentrated by evaporation. The residue is recrystallised from a small amount of hexane. 62 g (91.2 % of theory) of the desired product having a melting point of 61-62"C are obtained.

Example P2: 2-Hvdroxv-3-(3-DroDenvl)-4-chlorobenzoic acid methvl ester 97.9 g (0.432 mol) of 2-allyloxy-4-chlorobenzoic acid methyl ester (Example P1) are melted in a round-bottomed flask and irradiated in a microwave oven at 500 watts for 5 minutes. An exothermic reaction takes place. The reaction mixture is allowed to cool and yields 97.1 g (99.1 % of theory) of the desired product having a melting point of 32-35 C.

Example P3: 2-Oxv-(N, N-dimethyl-thiocarbamoyl)-3-(3-prnenl)-4-chlornbenzoic acid methvl ester 97 g (0.428 mol) of 2-hydroxy-3-(3-propenyl)-4-chlorobenzoic acid methyl ester (Example P2) and 69 g (0.5 mol) of potassium carbonate are stirred in 400 ml of dimethyl- formamide for 1/2 hour. A solution of 55.6 g (0.45 mol) of N,N-dimethyl-thiocarbamoyl chloride in 200 ml of dimethylformamide is then added dropwise thereto. The reaction mixture is stirred at 22°C for 22 hours. To complete the reaction, 11 g (0.09 mol) of N,N- dimethyl-thiocarbamoyl chloride and 15 g (0.11 mol) of potassium carbonate are added.

After a further 24 hours at 22"C, the reaction mixture is poured into an ice-water mixture and extracted by shaking with ethyl acetate. The ethyl acetate phase is washed with water, then with brine, dried over sodium sulfate and concentrated by evaporation. The residue is chromatographed on silica gel (eluant: ethyl acetate/hexane 1/3), yielding 114.5 g (85 % of theory) of the desired product in the form of an oil.

Example P4: 2-Mercapto-(N,N-dimethyl-carbamoyl)-3-(3-propenyl)-4-chlorob enzoic acid methvl ester 114.5 g (0.365 mol) of 2-oxy-(N,N-dimethyl-thiocarbamoyl)-3-(3-propenyl)-4-chlorobe nzoic acid methyl ester (Example P3) dissolved in 150 ml of diphenyl ether are added dropwise, in the course of 5 hours, to 100 ml of diphenyl ether at 205-210C. The temperature is maintained at 205°C for a further 1 1/2 hours. After cooling, the diphenyl ether is distilled off at a pressure of 0.04 mbar. The residue is chromatographed on silica gel (eluant: ethyl acetate/hexane 1/1), yielding 90.2 g (78.8 % of theory) of the desired product in the form of an oil.

Example P5: 4-Chloro-2-methvl-2,3-dihydro-benzo(bithiophene-7-carboxvlic acid (Comp. No. 1.001) 90.2 g (0.287 mol) of 2-mercapto-(N,N-dimethylcarbamoyl)-3-(3-propenyl)-4-chlorobe nzoic acid methyl ester (Example P4) is heated under reflux for 20 hours in 150 ml of acetic acid and 200 ml of concentrated hydrochloric acid. The reaction mixture is concentrated in a rotary evaporator and the residue is stirred with water and cooled. The solid substance is filtered off and drying is carried out in vacuo at 60 C, yielding 66 g (100 % of theory) of the expected product having a melting point of 215-218C.

Example P6: 4-Chloro-2-methvl-1 ,1-dioxo-2,3-dihydro-benzo[b]thiophene-7-carboxylic acid (Comp. No. 1.027) 20 g (0.0875 mol) of 4-chloro-2-methyl-2,3-dihydro-benzo[b]thiophene-7-carboxylic acid (Example P5) are suspended in 150 ml of acetic acid and heated to 70°C. 24 ml of approx.

35 % hydrogen peroxide are then added dropwise thereto. The reaction is exothermic. At 80"C, the heating bath is removed and the dropwise addition is continued in such a manner that the temperature remains at 80 C. The reaction mixture is then maintained at 70-75"C for 1 hour. The reaction mixture is then concentrated using a rotary evaporator until crystals are deposited. Water is then added; the mixture is cooled and the precipitated crystals are filtered off. After drying in vacuo at 60 C, 17 g (74 % of theory) of the desired product having a melting point of 223-225 C are obtained. Example P7: 4-Chloro-2-methVl-1,1-dioxo-2X3-dihydro-benzorbithiophene-7- carboxylic acid chloride 16.7 g (0.06 mol) of 4-chloro-2-methyl-1 ,1 -dioxo-2,3-dihydro-benzo[b]thiophene-7-carboxylic acid (Example P6) are heated to 90°C in 100 ml of toluene. 3 drops of dimethylformamide are added and then 9.5 g (0.08 mol) of thionyl chloride are added dropwise thereto in the course of 20 minutes, a clear solution being obtained. The reaction mixture is heated at 1 00CC for 3 hours and then concentrated by evaporation using a rotary evaporator, yielding 17 g of the desired product in the form of a solid substance.

Example P8: (2,3-Dihydro-4-chloro-2-methylbenzo[b]thiophen-7-yl)(2-hydro xy-6-oxo-1- cyclohexen-1 wI)methanone S.S-dioxide (Comp. No. 2.027) 9.5 g (0.094 mol) of triethylamine are added at 5°C to 3.6 g (0.0314 mol) of 1,3- cyclohexanedione in 80 ml of methylene chloride. At SC, 8.8 g (0.0314 mol) of 4-chloro-2- methyl-1,1-dioxo-2,3-dihydro-benzo[b]thiophene-7-carboxylic acid chloride (Example P7) in 20 ml of methylene chloride are added dropwise. After 1 hour at 22"C, 0.5 ml of acetone cyanohydrin are added. After 5 1/2 hours, the reaction mixture is extracted by shaking with 2N hydrochloric acid. The methylene chloride phase is separated off, dried with sodium sulfate and concentrated by evaporation, and the residue is dissolved in a small amount of warm acetone. On being left to stand the product crystallises out. After filtration, 5.5 g (50 % of theory) of the expected product having a melting point of 170-172"C are obtained.

Example P9: 4-Chloro-2-methyl-2,3-dihydro-benzo[b]thiophene-7-carboxylic acid chloride 45.7 g (0.2 mol) of 4-chloro-2-methyl-2,3-dihydro-benzo[b]thiophene-7-carboxylic acid (Example P5), 23.8 g (0.22 mol) of thionyl chloride and a few drops of dimethylformamide are heated in 300 ml of toluene at 100°C for 18 hours. Concentration by evaporation yields the desired product, which can be used further without purification.

Example P10: (2.3-DihVdro-4-chloro-2-methylbenzofbithiophen-7-yl)(1 ,3-dimethyl-5- hydroxy-1H-pyrazol-4-yl)methanone (Comp. No. 10.001) 2.3 g (0.02 mol) of 1 ,3-dimethylpyrazolone-5 and 2.2 g (0.022 mol) of triethylamine are suspended in 80 ml of ethyl acetate and cooled to 5°C, and then 5.0 g (0.02 mol) of 4- chloro-2-methyl-2,3-dihydro-benzo[b]thiophene-7-carboxylic acid chloride (Exampie P9) in 20 ml of ethyl acetate are added. The reaction mixture is stirred at 22°C for 18 hours, the salts are filtered off and concentration by evaporation is carried out using a rotary evaporator. The residue is dissolved in 70 ml of dimethylformamide, and 2.2 g (0.022 mol) of triethylamine and 0.2 g of potassium cyanide are added. The reaction mixture is left to stand at 22°C for 18 hours and the dimethylformamide is evaporated off. Ethyl acetate and 5 ml of glacial acetic acid are added to the residue and the resulting solution is extracted by shaking with water. The organic phase is separated off, dried with sodium sulfate and concentrated by evaporation. Trituration with diethyl ether yields the desired product having a melting point of 191-193°C. Example P1 1: (2,3-Dihvdro-4-ch loro-2-methylbenzo(bithioIohen-7-yl)(1 ,3-dimethyl-5- hydroxv-1 H-nvrazolA-vl)methanone S.S-dioxide (Comp. No. 10.027) 2.0 g (0.0115 mol) of 3-chloroperbenzoic acid dissolved in 30 ml of methylene chloride are added to 1.7 g (0.0052 mol) of (2,3-dihydro-4-chloro-2-methylbenzo[b]thiophen-7-yl)(1 ,3- dimethyl-5-hydroxy-1 H-pyrazol-4-yl)methanone (Example P10) in 40 ml of methylene chloride. The reaction mixture is left to stand at 22°C for 2 days and is extracted by shaking with saturated, aqueous sodium hydrogen carbonate solution. The hydrogen carbonate phase is acidified with concentrated hydrochloric acid and the resulting precipitate is filtered off. The solid substance so obtained is triturated with diethyl ether and isolated by filtration, yielding 1.6 g of the desired product having a melting point of 230-233 C.

In analogous manner, and in accordance with methods such as those described in the general Reaction Schemes 1 to 5 and the references indicated therein, it is also possible to prepare the preferred compounds listed in the following Tables.

Table 1: A preferred group of compounds of formula I corresponds to general formula Id wherein the meanings of the corresponding substituents R1 to R5 and n are given in Table A, so that 819 specific compounds of formula Id are disclosed.

Table 2: A further preferred group of compounds of formula I corresponds to general formula Ig wherein the meanings of the corresponding substituents R1 to R5 and n are given in Table A, so that 819 specific compounds of formula Ig are disclosed.

Table 3: A further preferred group of compounds of formula I corresponds to general formula Ih wherein the meanings of the corresponding substituents R1 to R5 and n are given in Table A, so that 819 specific compounds of formula Ih are disclosed.

Table 4: A further preferred group of compounds of formula I corresponds to general formula li wherein the meanings of the corresponding substituents R1 to R5 and n are given in Table A, so that 819 specific compounds of formula li are disclosed.

Table 5: A further preferred group of compounds of formula I corresponds to general formula Ij wherein the meanings of the corresponding substituents R1 to R5 and n are given in Table A, so that 819 specific compounds of formula Ij are disclosed. Table 6: A further preferred group of compounds of formula I corresponds to general formula lk wherein the meanings of the corresponding substituents R1 to R5 and n are given in Table A, so that 819 specific compounds of formula lk are disclosed.

Table A Compd. R2 R1 R3 R4 R5 n No.

.001 H CH3 H H Cl 0 .002 H CH3 H H F 0 .003 H CH3 H H Br 0 .004 H CH3 H H SO2Me 0 .005 H CH3 H H SMe 0 .006 H CH3 H H SO2NMe2 O .007 H CH3 H H CF3 0 .008 H CH3 H H CH3 0 .009 H CH3 H H CH(CH3)2 O .010 H CH3 H H NO2 0 .011 H CH3 H H OCH3 0 .012 H CH3 H H OCF2CF3 0 .013 H CH3 H H CN 0 .014 H CH3 H H Cl 1 .015 H CH3 H H F 1 .016 H CH3 H H Br 1 .017 H CH3 H H SO2Me 1 .018 H CH3 H H SMe 1 .019 H CH3 H H SO2NMe2 1 .020 H CH3 H H CF3 1 Compd. R2 R1 R3 R4 R5 n No.

.021 H CH3 H H CH3 1 .022 H CH3 H H CH(CH3)2 1 .023 H CH3 H H NO2 1 .024 H CH3 H H OCH3 1 .025 H CH3 H H OCF2CF3 1 .026 H CH3 H H CN 1 .027 H CH3 H H Cl 2 .028 H CH3 H H F 2 .029 H CH3 H H Br 2 .030 H CH3 H H SO2Me 2 .031 H CH3 H H SMe 2 .032 H CH3 H H SO2NMe2 2 .033 H CH3 H H CF3 2 .034 H CH3 H H CH3 2 .035 H CH3 H H CH(CH3)2 2 .036 H CH3 H H NO2 2 .037 H CH3 H H OCH3 2 .038 H CH3 H H OCF2CF3 2 .039 H CH3 H H CN 2 .040 H CH3CH2 H H Cl 0 .041 H CH3CH2 H H F 0 .042 H CH3CH2 H H Br 0 .043 H CH3CH2 H H SO2Me 0 .044 H CH3CH2 H H SMe 0 .045 H CH3CH2 H H SO2NMe2 0 .046 H CH3CH2 H H CF3 0 .047 H CH3CH2 H H CH3 0 .048 H CH3CH2 H H CH(CH3)2 O .049 H CH3CH2 H H NO2 0 .050 H CH3CH2 H H OCH3 0 .051 H CH3CH2 H H OCF2CF3 0 Compd. R2 R1 R3 R4 R5 n No.

.052 H CH3CH2 H H CN 0 .053 H CH3CH2 H H Cl 1 .054 H CH3CH2 H H F 1 .055 H CH3CH2 H H Br 1 .056 H CH3CH2 H H SO2Me 1 .057 H CH3CH2 H H SMe 1 .058 H CH3CH2 H H SO2NMe2 1 .059 H CH3CH2 H H CF3 1 .060 H CH3CH2 H H CH3 1 .061 H CH3CH2 H H CH(CH3)2 1 .062 H CH3CH2 H H NO2 1 .063 H CH3CH2 H H OCH3 1 .064 H CH3CH2 H H OCF2CF3 1 .065 H CH3CH2 H H CN 1 .066 H CH3CH2 H H CI 2 .067 H CH3CH2 H H F 2 .068 H CH3CH2 H H Br 2 .069 H CH3CH2 H H SO2Me 2 .070 H CH3CH2 H H SMe 2 .071 H CH3CH2 H H SO2NMe2 2 .072 H CH3CH2 H H CF3 2 .073 H CH3CH2 H H CH3 2 .074 H CH3CH2 H H CH(CH3)2 2 .075 H CH3CH2 H H NO2 2 .076 H CH3CH2 H H OCH3 2 .077 H CH3CH2 H H OCF2CF3 2 .078 H CH3CH2 H H CN 2 .079 CH3 CH3CH2 H H Cl 0 .080 CH3 CH3CH2 H H F 0 .081 CH3 CH3CH2 H H Br 0 .082 CH3 CH3CH2 H H SO2Me 0 Compd. R2 R1 R3 R4 R5 n No.

.083 CH3 CH3CH2 H H SMe 0 .084 CH3 CH3CH2 H H SO2NMe2 0 .085 CH3 CH3CH2 H H CF3 0 .086 CH3 CH3CH2 H H CH3 0 .087 CH3 CH3CH2 H H CH(CH3)2 O .088 CH3 CH3CH2 H H NO2 0 .089 CH3 CH3CH2 H H OCH3 0 .090 CH3 CH3CH2 H H OCF2CF3 0 .091 CH3 CH3CH2 H H CN 0 .092 CH3 CH3CH2 H H Cl 1 .093 CH3 CH3CH2 H H F 1 .094 CH3 CH3CH2 H H Br 1 .095 CH3 CH3CH2 H H SO2Me 1 .096 CH3 CH3CH2 H H SMe 1 .097 CH3 CH3CH2 H H SO2NMe2 1 .098 CH3 CH3CH2 H H CF3 1 .099 CH3 CH3CH2 H H CH3 1 .100 CH3 CH3CH2 H H CH(CH3)2 1 .101 CH3 CH3CH2 H H NO2 1 .102 CH3 CH3CH2 H H OCH3 1 .103 CH3 CH3CH2 H H OCF2CF3 1 .104 CH3 CH3CH2 H H CN 1 .105 CH3 CH3CH2 H H Cl 2 .106 CH3 CH3CH2 H H F 2 .107 CH3 CH3CH2 H H Br 2 .108 CH3 CH3CH2 H H SO2Me 2 .109 CH3 CH3CH2 H H SMe 2 .110 CH3 CH3CH2 H H SO2NMe2 2 .111 CH3 CH3CH2 H H CF3 2 .112 CH3 CH3CH2 H H CH3 2 .113 CH3 CH3CH2 H H CH(CH3)2 2 Compd. R2 R1 R3 R4 R5 n No.

.114 CH3 CH3CH2 H H NO2 2 .115 CH3 CH3CH2 H H OCH3 2 .116 CH3 CH3CH2 H H OCF2CF3 2 .117 CH3 CH3CH2 H H CN 2 .118 H CH3 H CH3 Cl 0 .119 H CH3 H CH3 F 0 .120 H CH3 H CH3 Br 0 .121 H CH3 H CH3 SO2Me 0 .122 H CH3 H CH3 SMe 0 .123 H CH3 H CH3 SO2NMe2 0 .124 H CH3 H CH3 CF3 0 .125 H CH3 H CH3 CH3 0 .126 H CH3 H CH3 CH(CH3)2 O .127 H CH3 H CH3 NO2 O .128 H CH3 H CH3 OCH3 0 .129 H CH3 H CH3 OCF2CF3 0 .130 H CH3 H CH3 CN 0 .131 H CH3 H CH3 Cl 1 .132 H CH3 H CH3 F 1 .133 H CH3 H CH3 Br 1 .134 H CH3 H CH3 SO2Me .135 H CH3 H CH3 SMe 1 .136 H CH3 H CH3 SO2NMe2 1 .137 H CH3 H CH3 CF3 1 .138 H CH3 H CH3 CH3 1 .139 H CH3 H CH3 CH(CH3)2 1 .140 H CH3 H CH3 NO2 .141 H CH3 H CH3 OCH3 1 .142 H CH3 H CH3 OCF2CF3 1 .143 H CH3 H CH3 CN 1 .144 H CH3 H CH3 CI 2 Compd. R2 R1 R3 R4 R5 n No.

.145 H CH3 H CH3 F 2 .146 H CH3 H CH3 Br 2 .147 H CH3 H CH3 SO2Me 2 .148 H CH3 H CH3 SMe 2 .149 H CH3 H CH3 SO2NMe2 2 .150 H CH3 H CH3 CF3 2 .151 H CH3 H CH3 CH3 2 .152 H CH3 H CH3 CH(CH3)2 2 .153 H CH3 H CH3 NO2 2 .154 H CH3 H CH3 OCH3 2 .155 H CH3 H CH3 OCF2CF3 2 .156 H CH3CH2 H CH3 CN 2 .157 H CH3CH2 H CH3 CI 0 .158 H CH3CH2 H CH3 F 0 .159 H CH3CH2 H CH3 Br 0 .160 H CH3CH2 H CH3 SO2Me 0 .161 H CH3CH2 H CH3 SMe 0 .162 H CH3CH2 H CH3 SO2NMe2 0 .163 H CH3CH2 H CH3 CF3 0 .164 H CH3CH2 H CH3 CH3 0 .165 H CH3CH2 H CH3 CH(CH3)2 O .166 H CH3CH2 H CH3 NO2 O .167 H CH3CH2 H CH3 OCH3 0 .168 H CH3CH2 H CH3 OCF2CF3 0 .169 H CH3CH2 H CH3 CN 0 .170 H CH3CH2 H CH3 Cl 1 .171 H CH3CH2 H CH3 F 1 .172 H CH3CH2 H CH3 Br 1 .173 H CH3CH2 H CH3 SO2Me 1 .174 H CH3CH2 H CH3 SMe 1 .175 H CH3CH2 H CH3 SO2NMe2 1 Compd. R2 R1 R3 R4 R5 n No.

.176 H CH3CH2 H CH3 CF3 1 .177 H CH3CH2 H CH3 CH3 1 .178 H CH3CH2 H CH3 CH(CH3)2 1 .179 H CH3CH2 H CH3 NO2 1 .180 H CH3CH2 H CH3 OCH3 1 .181 H CH3CH2 H CH3 OCF2CF3 1 .182 H CH3CH2 H CH3 CN 1 .183 H CH3CH2 H CH3 Cl 2 .184 H CH3CH2 H CH3 F 2 .185 H CH3CH2 H CH3 Br 2 .186 H CH3CH2 H CH3 SO2Me 2 .187 H CH3CH2 H CH3 SMe 2 .188 H CH3CH2 H CH3 SO2NMe2 2 .189 H CH3CH2 H CH3 CF3 2 .190 H CH3CH2 H CH3 CH3 2 .191 H CH3CH2 H CH3 CH(CH3)2 2 .192 H CH3CH2 H CH3 NO2 2 .193 H CH3CH2 H CH3 OCH3 2 .194 H CH3CH2 H CH3 OCF2CF3 2 .195 H CH3CH2 H CH3 CN 2 .196 CH3 CH3CH2 H CH3 CI 0 .197 CH3 CH3CH2 H CH3 F 0 .198 CH3 CH3CH2 H CH3 Br 0 .199 CH3 CH3CH2 H CH3 SO2Me 0 .200 CH3 CH3CH2 H CH3 SMe 0 .201 CH3 CH3CH2 H CH3 SO2NMe2 0 .202 CH3 CH3CH2 H CH3 CF3 0 .203 CH3 CH3CH2 H CH3 CH3 0 .204 CH3 CH3CH2 H CH3 CH(CH3)2 O .205 CH3 CH3CH2 H CH3 NO2 O .206 CH3 CH3CH2 H CH3 OCH3 0 Compd. R2 R1 R3 R4 R5 n No.

.207 CH3 CH3CH2 H CH3 OCF2CF3 0 .208 CH3 CH3CH2 H CH3 CN 0 .209 CH3 CH3CH2 H CH3 CI 1 .210 CH3 CH3CH2 H CH3 F 1 .211 CH3 CH3CH2 H CH3 Br 1 .212 CH3 CH3CH2 H CH3 SO2Me 1 .213 CH3 CH3CH2 H CH3 SMe 1 .214 CH3 CH3CH2 H CH3 SO2NMe2 1 .215 CH3 CH3CH2 H CH3 CF3 1 .216 CH3 CH3CH2 H CH3 CH3 1 .217 CH3 CH3CH2 H CH3 CH(CH3)2 1 .218 CH3 CH3CH2 H CH3 NO2 .219 CH3 CH3CH2 H CH3 OCH3 1 .220 CH3 CH3CH2 H CH3 OCF2CF3 1 .221 CH3 CH3CH2 H CH3 CN 1 .222 CH3 CH3CH2 H CH3 Cl 2 .223 CH3 CH3CH2 H CH3 F 2 .224 CH3 CH3CH2 H CH3 Br 2 .225 CH3 CH3CH2 H CH3 SO2Me 2 .226 CH3 CH3CH2 H CH3 SMe 2 .227 CH3 CH3CH2 H CH3 SO2NMe2 2 .228 CH3 CH3CH2 H CH3 CF3 2 .229 CH3 CH3CH2 H CH3 CH3 2 .230 CH3 CH3CH2 H CH3 CH(CH3)2 2 .231 CH3 CH3CH2 H CH3 NO2 2 .232 CH3 CH3CH2 H CH3 OCH3 2 .233 CH3 CH3CH2 H CH3 OCF2CF3 2 .234 CH3 CH3CH2 H CH3 CN 2 .235 CH3 CH3CH2 CH3 CH3 Cl 0 .236 CH3 CH3CH2 CH3 CH3 F 0 .237 CH3 CH3CH2 CH3 CH3 Br 0 Compd. R2 R1 R3 R4 R5 n No.

.238 CH3 CH3CH2 CH3 CH3 SO2Me 0 .239 CH3 CH3CH2 CH3 CH3 SMe 0 .240 CH3 CH3CH2 CH3 CH3 SO2NMe2 0 .241 CH3 CH3CH2 CH3 CH3 CF3 0 .242 CH3 CH3CH2 CH3 CH3 CH3 0 .243 CH3 CH3CH2 CH3 CH3 CH(CH3)2 O .244 CH3 CH3CH2 CH3 CH3 NO2 O .245 CH3 CH3CH2 CH3 CH3 OCH3 0 .246 CH3 CH3CH2 CH3 CH3 OCF2CF3 0 .247 CH3 CH3CH2 CH3 CH3 CN 0 .248 CH3 CH3CH2 CH3 CH3 Cl 1 .249 CH3 CH3CH2 CH3 CH3 F 1 .250 CH3 CH3CH2 CH3 CH3 Br 1 .251 CH3 CH3CH2 CH3 CH3 SO2Me .252 CH3 CH3CH2 CH3 CH3 SMe 1 .253 CH3 CH3CH2 CH3 CH3 SO2NMe2 1 .254 CH3 CH3CH2 CH3 CH3 CF3 .255 CH3 CH3CH2 CH3 CH3 CH3 1 .256 CH3 CH3CH2 CH3 CH3 CH(CH3)2 1 .257 CH3 CH3CH2 CH3 CH3 NO2 1 .258 CH3 CH3CH2 CH3 CH3 OCH3 1 .259 CH3 CH3CH2 CH3 CH3 OCF2CF3 1 .260 CH3 CH3CH2 CH3 CH3 CN 1 .261 CH3 CH3CH2 CH3 CH3 Cl 2 .262 CH3 CH3CH2 CH3 CH3 F 2 .263 CH3 CH3CH2 CH3 CH3 Br 2 .264 CH3 CH3CH2 CH3 CH3 SO2Me 2 .265 CH3 CH3CH2 CH3 CH3 SMe 2 .266 CH3 CH3CH2 CH3 CH3 SO2NMe2 2 .267 CH3 CH3CH2 CH3 CH3 CF3 2 .268 CH3 CH3CH2 CH3 CH3 CH3 2 Compd. R2 R1 R3 R4 R5 n No.

.269 CH3 CH3CH2 CH3 CH3 CH(CH3)2 2 .270 CH3 CH3CH2 CH3 CH3 NO2 2 .271 CH3 CH3CH2 CH3 CH3 OCH3 2 .272 CH3 CH3CH2 CH3 CH3 OCF2CF3 2 .273 CH3 CH3CH2 CH3 CH3 CN 2 .274 H CH3 H CI Cl 0 .275 H CH3 H Cl F 0 .276 H CH3 H CI Br 0 .277 H CH3 H CI SO2Me 0 .278 H CH3 H Cl SMe 0 .279 H CH3 H Cl SO2NMe2 0 .280 H CH3 H CI CF3 0 .281 H CH3 H Cl CH3 0 .282 H CH3 H Cl CH(CH3)2 0 .283 H CH3 H Cl NO2 0 .284 H CH3 H CI OCH3 0 .285 H CH3 H Cl OCF2CF3 0 .286 H CH3 H Cl CN 0 .287 H CH3 H Cl Cl 1 .288 H CH3 H Cl F 1 .289 H CH3 H Cl Br 1 .290 H CH3 H CI SO2Me 1 .291 H CH3 H Cl SMe 1 .292 H CH3 H Cl SO2NMe2 1 .293 H CH3 H Cl CF3 1 .294 H CH3 H Cl CH3 1 .295 H CH3 H Cl CH(CH3)2 1 .296 H CH3 H Cl NO2 1 .297 H CH3 H Cl OCH3 1 .298 H CH3 H Cl OCF2CF3 1 .299 H CH3 H Cl CN 1 Compd. R2 R1 R3 R4 R5 n No.

.300 H CH3 H Cl CI 2 .301 H CH3 H CI F 2 .302 H CH3 H CI Br 2 .303 H CH3 H Cl SO2Me 2 .304 H CH3 H CI SMe 2 .305 H CH3 H Cl SO2NMe2 2 .306 H CH3 H CI CF3 2 .307 H CH3 H Cl CH3 2 .308 H CH3 H Cl CH(CH3)2 2 .309 H CH3 H Cl NO2 2 .310 H CH3 H CI OCH3 2 .311 H CH3 H Cl OCF2CF3 2 .312 H CH3 H CI CN 2 .313 H CH3CH2 H Cl Cl 0 .314 H CH3CH2 H CI F 0 .315 H CH3CH2 H CI Br 0 .316 H CH3CH2 H CI SO2Me 0 .317 H CH3CH2 H Cl SMe 0 .318 H CH3CH2 H Cl SO2NMe2 0 .319 H CH3CH2 H Cl CF3 0 .320 H CH3CH2 H CI CH3 0 .321 H CH3CH2 H Cl CH(CH3)2 O .322 H CH3CH2 H CI NO2 0 .323 H CH3CH2 H Cl OCH3 0 .324 H CH3CH2 H CI OCF2CF3 0 .325 H CH3CH2 H CI CN 0 .326 H CH3CH2 H Cl Cl 1 .327 H CH3CH2 H Cl F 1 .328 H CH3CH2 H Cl Br 1 .329 H CH3CH2 H Cl SO2Me 1 .330 H CH3CH2 H Cl SMe 1 Compd. R2 R1 R3 R4 R5 n No.

.331 H CH3CH2 H Cl SO2NMe2 1 .332 H CH3CH2 H CI CF3 1 .333 H CH3CH2 H Cl CH3 1 .334 H CH3CH2 H Cl CH(CH3)2 1 .335 H CH3CH2 H CI NO2 1 .336 H CH3CH2 H Cl OCH3 1 .337 H CH3CH2 H Cl OCF2CF3 1 .338 H CH3CH2 H CI CN 1 .339 H CH3CH2 H CI CI 2 .340 H CH3CH2 H CI F 2 .341 H CH3CH2 H CI Br 2 .342 H CH3CH2 H CI SO2Me 2 .343 H CH3CH2 H CI SMe 2 .344 H CH3CH2 H Cl SO2NMe2 2 .345 H CH3CH2 H CI CF3 2 .346 H CH3CH2 H CI CH3 2 .347 H CH3CH2 H Cl CH(CH3)2 2 .348 H CH3CH2 H Cl NO2 2 .349 H CH3CH2 H Cl OCH3 2 .350 H CH3CH2 H Cl OCF2CF3 2 .351 H CH3CH2 H Cl CN 2 .352 CH3 CH3CH2 H Cl CI 0 .353 CH3 CH3CH2 H CI F 0 .354 CH3 CH3CH2 H Cl Br 0 .355 CH3 CH3CH2 H Cl SO2Me 0 .356 CH3 CH3CH2 H CI SMe 0 .357 CH3 CH3CH2 H Cl SO2NMe2 0 .358 CH3 CH3CH2 H Cl CF3 0 .359 CH3 CH3CH2 H Cl CH3 0 .360 CH3 CH3CH2 H Cl CH(CH3)2 O .361 CH3 CH3CH2 H Cl NO2 0 Compd. R2 R1 R3 R4 R5 n No.

.362 CH3 CH3CH2 H Cl OCH3 0 .363 CH3 CH3CH2 H Cl OCF2CF3 0 .364 CH3 CH3CH2 H CI CN 0 .365 CH3 CH3CH2 H Cl Cl 1 .366 CH3 CH3CH2 H CI F 1 .367 CH3 CH3CH2 H CI Br 1 .368 CH3 CH3CH2 H Cl SO2Me 1 .369 CH3 CH3CH2 H Cl SMe 1 .370 CH3 CH3CH2 H Cl SO2NMe2 1 .371 CH3 CH3CH2 H Cl CF3 1 .372 CH3 CH3CH2 H CI CH3 1 .373 CH3 CH3CH2 H Cl CH(CH3)2 1 .374 CH3 CH3CH2 H Cl NO2 1 .375 CH3 CH3CH2 H Cl OCH3 1 .376 CH3 CH3CH2 H Cl OCF2CF3 1 .377 CH3 CH3CH2 H CI CN 1 .378 CH3 CH3CH2 H CI CI 2 .379 CH3 CH3CH2 H CI F 2 .380 CH3 CH3CH2 H Cl Br 2 .381 CH3 CH3CH2 H Cl SO2Me 2 .382 CH3 CH3CH2 H Cl SMe 2 .383 CH3 CH3CH2 H Cl SO2NMe2 2 .384 CH3 CH3CH2 H Cl CF3 2 .385 CH3 CH3CH2 H Cl CH3 2 .386 CH3 CH3CH2 H Cl CH(CH3)2 2 .387 CH3 CH3CH2 H Cl NO2 2 .388 CH3 CH3CH2 H Cl OCH3 2 .389 CH3 CH3CH2 H Cl OCF2CF3 2 .390 CH3 CH3CH2 H Cl CN 2 .391 H CH3 H H CI 0 .392 H CH3 H H F 0 Compd. R2 R1 R3 R4 R5 n No.

.393 H CH3 H H Br 0 .394 H CH3 H H SO2Me 0 .395 H CH3 H H SMe 0 .396 H CH3 H H SO2NMe2 0 .397 H CH3 H H CF3 0 .398 H CH3 H H CH3 0 .399 H CH3 H H CH(CH3)2 O .400 H CH3 H H NO2 0 .401 H CH3 H H OCH3 0 .402 H CH3 H H OCF2CF3 0 .403 H CH3 H H CN 0 .404 H CH3 H H Cl 1 .405 H CH3 H H F 1 .406 H CH3 H H Br 1 .407 H CH3 H H SO2Me 1 .408 H CH3 H H SMe 1 .409 H CH3 H H SO2NMe2 1 .410 H CH3 H H CF3 1 .411 H CH3 H H CH3 1 .412 H CH3 H H CH(CH3)2 1 .413 H CH3 H H NO2 1 .414 H CH3 H H OCH3 1 .415 H CH3 H H OCF2CF3 1 .416 H CH3 H H CN 1 .417 H CH3 H H Cl 2 .418 H CH3 H H F 2 .419 H CH3 H H Br 2 .420 H CH3 H H SO2Me 2 .421 H CH3 H H SMe 2 .422 H CH3 H H SO2NMe2 2 .423 H CH3 H H CF3 2 Compd. R2 R1 R3 R4 R5 n No.

.424 H CH3 H H CH3 2 .425 H CH3 H H CH(CH3)2 2 .426 H CH3 H H NO2 2 .427 H CH3 H H OCH3 2 .428 H CH3 H H OCF2CF3 2 .429 H CH3 H H CN 2 .430 H CH2OH H H Cl 0 .431 H CH2OH H H F 0 .432 H CH2OH H H Br 0 .433 H CH2OH H H SO2Me 0 .434 H CH2OH H H SMe 0 .435 H CH2OH H H SO2NMe2 0 .436 H CH2OH H H CF3 0 .437 H CH2OH H H CH3 0 .438 H CH2OH H H CH(CH3)2 O .439 H CH2OH H H NO2 0 .440 H CH2OH H H OCH3 0 .441 H CH2OH H H OCF2CF3 0 .442 H CH2OH H H CN 0 .443 H CH2OH H H Cl 1 .444 H CH2OH H H F 1 .445 H CH2OH H H Br 1 .446 H CH2OH H H SO2Me 1 .447 H CH2OH H H SMe 1 .448 H CH2OH H H SO2NMe2 1 .449 H CH2OH H H CF3 1 .450 H CH2OH H H CH3 1 .451 H CH2OH H H CH(CH3)2 1 .452 H CH2OH H H NO2 1 .453 H CH2OH H H OCH3 1 .454 H CH2OH H H OCF2CF3 1 Compd. R2 R1 R3 R4 R5 n No.

.455 H CH20H H H CN 1 .456 H CH20H H H CI 2 .457 H CH2OH H H F 2 .458 H CH2OH H H Br 2 .459 H CH2OH H H SO2Me 2 .460 H CH2OH H H SMe 2 .461 H CH2OH H H SO2NMe2 2 .462 H CH2OH H H CF3 2 .463 H CH2OH H H CH3 2 .464 H CH2OH H H CH(CH3)2 2 .465 H CH2OH H H NO2 2 .466 H CH2OH H H OCH3 2 .467 H CH2OH H H OCF2CF3 2 .468 H CH20H H H CN 2 .469 H CO2CH3 H H CI 0 .470 H CO2CH3 H H F 0 .471 H CO2CH3 H H Br 0 .472 H CO2CH3 H H SO2Me 0 .473 H CO2CH3 H H SMe 0 .474 H CO2CH3 H H SO2NMe2 0 .475 H CO2CH3 H H CF3 0 .476 H CO2CH3 H H CH3 0 .477 H CO2CH3 H H CH(CH3)2 O .478 H CO2CH3 H H NO2 0 .479 H CO2CH3 H H OCH3 0 .480 H CO2CH3 H H OCF2CF3 0 .481 H CO2CH3 H H CN 0 .482 H CO2CH3 H H Cl 1 .483 H CO2CH3 H H F 1 .484 H CO2CH3 H H Br 1 .485 H CO2CH3 H H SO2Me 1 Compd. R2 R1 R3 R4 R5 n No.

.486 H CO2CH3 H H SMe 1 .487 H CO2CH3 H H SO2NMe2 1 .488 H CO2CH3 H H CF3 1 .489 H CO2CH3 H H CH3 1 .490 H CO2CH3 H H CH(CH3)2 1 .491 H CO2CH3 H H NO2 1 .492 H CO2CH3 H H OCH3 1 .493 H CO2CH3 H H OCF2CF3 1 .494 H CO2CH3 H H CN 1 .495 H CO2CH3 H H Cl 2 .496 H CO2CH3 H H F 2 .497 H CO2CH3 H H Br 2 .498 H CO2CH3 H H SO2Me 2 .499 H CO2CH3 H H SMe 2 .500 H CO2CH3 H H SO2NMe2 2 .501 H CO2CH3 H H CF3 2 .502 H CO2CH3 H H CH3 2 .503 H CO2CH3 H H CH(CH3)2 2 .504 H CO2CH3 H H NO2 2 .505 H CO2CH3 H H OCH3 2 .506 H CO2CH3 H H OCF2CF3 2 .507 H CO2CH3 H H CN 2 .508 H CH=O H H Cl 0 .509 H CH=O H H F 0 .510 H CH=O H H Br 0 .511 H CH=O H H SO2Me 0 .512 H CH=O H H SMe 0 .513 H CH=O H H SO2NMe2 0 .514 H CH=O H H CF3 0 .515 H CH=O H H CH3 0 .516 H CH=O H H CH(CH3)2 O Compd. R2 R1 R3 R4 R5 n No.

.517 H CH=O H H NO2 0 .518 H CH=O H H OCH3 0 .519 H CH=O H H OCF2CF3 0 .520 H CH=O H H CN 0 .521 H CH=O H H Cl 1 .522 H CH=O H H F 1 .523 H CH=O H H Br 1 .524 H CH=O H H SO2Me 1 .525 H CH=O H H SMe 1 .526 H CH=O H H SO2NMe2 1 .527 H CH=O H H CF3 1 .528 H CH=O H H CH3 1 .529 H CH=O H H CH(CH3)2 1 .530 H CH=O H H NO2 1 .531 H CH=O H H OCH3 1 .532 H CH=O H H OCF2CF3 1 .533 H CH=O H H CN 1 .534 H CH=O H H Cl 2 .535 H CH=O H H F 2 .536 H CH=O H H Br 2 .537 H CH=O H H SO2Me 2 .538 H CH=O H H SMe 2 .539 H CH=O H H SO2NMe2 2 .540 H CH=O H H CF3 2 .541 H CH=O H H CH3 2 .542 H CH=O H H CH(CH3)2 2 .543 H CH=O H H NO2 2 .544 H CH=O H H OCH3 2 .545 H CH=O H H OCF2CF3 2 .546 H CH=O H H CN 2 .547 H CH=NOCH3 H H Cl 0 Compd. R2 R1 R3 R4 R5 n No.

.548 H CH=NOCH3 H H F 0 .549 H CH=NOCH3 H H Br 0 .550 H CH=NOCH3 H H SO2Me 0 .551 H CH=NOCH3 H H SMe 0 .552 H CH=NOCH3 H H SO2NMe2 0 .553 H CH=NOCH3 H H CF3 0 .554 H CH=NOCH3 H H CH3 0 .555 H CH=NOCH3 H H CH(CH3)2 O .556 H CH=NOCH3 H H NO2 0 .557 H CH=NOCH3 H H OCH3 0 .558 H CH=NOCH3 H H OCF2CF3 0 .559 H CH=NOCH3 H H CN 0 .560 H CH=NOCH3 H H Cl 1 .561 H CH=NOCH3 H H F 1 .562 H CH=NOCH3 H H Br 1 .563 H CH=NOCH3 H H SO2Me 1 .564 H CH=NOCH3 H H SMe 1 .565 H CH=NOCH3 H H SO2NMe2 1 .566 H CH=NOCH3 H H CF3 1 .567 H CH=NOCH3 H H CH3 1 .568 H CH=NOCH3 H H CH(CH3)2 1 .569 H CH=NOCH3 H H NO2 1 .570 H CH=NOCH3 H H OCH3 1 .571 H CH=NOCH3 H H OCF2CF3 1 .572 H CH=NOCH3 H H CN 1 .573 H CH=NOCH3 H H Cl 2 .574 H CH=NOCH3 H H F 2 .575 H CH=NOCH3 H H Br 2 .576 H CH=NOCH3 H H SO2Me 2 .577 H CH=NOCH3 H H SMe 2 .578 H CH=NOCH3 H H SO2NMe2 2 Compd. R2 R1 R3 R4 R5 n No.

.579 H CH=NOCH3 H H CF3 2 .580 H CH=NOCH3 H H CH3 2 .581 H CH=NOCH3 H H CH(CH3)2 2 .582 H CH=NOCH3 H H NO2 2 .583 H CH=NOCH3 H H OCH3 2 .584 H CH=NOCH3 H H OCF2CF3 2 .585 H CH=NOCH3 H H CN 2 .586 H CH2NH2 H H Cl 0 .587 H CH2NH2 H H F 0 .588 H CH2NH2 H H Br 0 .589 H CH2NH2 H H SO2Me 0 .590 H CH2NH2 H H SMe 0 .591 H CH2NH2 H H SO2NMe2 0 .592 H CH2NH2 H H CF3 0 .593 H CH2NH2 H H CH3 0 .594 H CH2NH2 H H CH(CH3)2 O .595 H CH2NH2 H H NO2 0 .596 H CH2NH2 H H OCH3 0 .597 H CH2NH2 H H OCF2CF3 0 .598 H CH2NH2 H H CN 0 .599 H CH2NH2 H H Cl 1 .600 H CH2NH2 H H F 1 .601 H CH2NH2 H H Br 1 .602 H CH2NH2 H H SO2Me .603 H CH2NH2 H H SMe 1 .604 H CH2NH2 H H SO2NMe2 1 .605 H CH2NH2 H H CF3 1 .606 H CH2NH2 H H CH3 1 .607 H CH2NH2 H H CH(CH3)2 1 .608 H CH2NH2 H H NO2 .609 H CH2NH2 H H OCH3 1 Compd. R2 R1 R3 R4 R5 n No.

.610 H CH2NH2 H H OCF2CF3 1 .611 H CH2NH2 H H CN 1 .612 H CH2NH2 H H CI 2 .613 H CH2NH2 H H F 2 .614 H CH2NH2 H H Br 2 .615 H CH2NH2 H H SO2Me 2 .616 H CH2NH2 H H SMe 2 .617 H CH2NH2 H H SO2NMe2 2 .618 H CH2NH2 H H CF3 2 .619 H CH2NH2 H H CH3 2 .620 H CH2NH2 H H CH(CH3)2 2 .621 H CH2NH2 H H NO2 2 .622 H CH2NH2 H H OCH3 2 .623 H CH2NH2 H H OCF2CF3 2 .624 H CH2NH2 H H CN 2 .625 H CN H H Cl 0 .626 H CN H H F 0 .627 H CN H H Br 0 .628 H CN H H SO2Me 0 .629 H CN H H SMe 0 .630 H CN H H SO2NMe2 0 .631 H CN H H CF3 0 .632 H CN H H CH3 0 .633 H CN H H CH(CH3)2 O .634 H CN H H NO2 0 .635 H CN H H OCH3 0 .636 H CN H H OCF2CF3 0 .637 H CN H H CN 0 .638 H CN H H Cl 1 .639 H CN H H F 1 .640 H CN H H Br 1 Compd. R2 R1 R3 R4 R5 n No.

.641 H CN H H SO2Me 1 .642 H CN H H SMe 1 .643 H CN H H SO2NMe2 1 .644 H CN H H CF3 1 .645 H CN H H CH3 1 .646 H CN H H CH(CH3)2 1 .647 H CN H H NO2 1 .648 H CN H H OCH3 1 .649 H CN H H OCF2CF3 1 .650 H CN H H CN 1 .651 H CN H H Cl 2 .652 H CN H H F 2 .653 H CN H H Br 2 .654 H CN H H SO2Me 2 .655 H CN H H SMe 2 .656 H CN H H SO2NMe2 2 .657 H CN H H CF3 2 .658 H CN H H CH3 2 .659 H CN H H CH(CH3)2 2 .660 H CN H H NO2 2 .661 H CN H H OCH3 2 .662 H CN H H OCF2CF3 2 .663 H CN H H CN 2 .664 H CH(OH)CH3 H H Cl 0 .665 H CH(OH)CH3 H H F 0 .666 H CH(OH)CH3 H H Br o .667 H CH(OH)CH3 H H SO2Me 0 .668 H CH(OH)CH3 H H SMe 0 .669 H CH(OH)CH3 H H SO2NMe2 O .670 H CH(OH)CH3 H H CF3 0 .671 H CH(OH)CH3 H H CH3 0 Compd. R2 R1 R3 R4 R5 n No.

.672 H CH(OH)CH3 H H CH(CH3)2 O .673 H CH(OH)CH3 H H NO2 0 .674 H CH(OH)CH3 H H OCH3 0 .675 H CH(OH)CH3 H H OCF2CF3 0 .676 H CH(OH)CH3 H H CN 0 .677 H CH(OH)CH3 H H Cl 1 .678 H CH(OH)CH3 H H F 1 .679 H CH(OH)CH3 H H Br 1 .680 H CH(OH)CH3 H H SO2Me 1 .681 H CH(OH)CH3 H H SMe 1 .682 H CH(OH)CH3 H H SO2NMe2 1 .683 H CH(OH)CH3 H H CF3 1 .684 H CH(OH)CH3 H H CH3 1 .685 H CH(OH)CH3 H H CH(CH3)2 1 .686 H CH(OH)CH3 H H NO2 .687 H CH(OH)CH3 H H OCH3 1 .688 H CH(OH)CH3 H H OCF2CF3 1 .689 H CH(OH)CH3 H H CN 1 .690 H CH(OH)CH3 H H Cl 2 .691 H CH(OH)CH3 H H F 2 .692 H CH(OH)CH3 H H Br 2 .693 H CH(OH)CH3 H H SO2Me 2 .694 H CH(OH)CH3 H H SMe 2 .695 H CH(OH)CH3 H H SO2NMe2 2 .696 H CH(OH)CH3 H H CF3 2 .697 H CH(OH)CH3 H H CH3 2 .698 H CH(OH)CH3 H H CH(CH3)2 2 .699 H CH(OH)CH3 H H NO2 2 .700 H CH(OH)CH3 H H OCH3 2 .701 H CH(OH)CH3 H H OCF2CF3 2 .702 H CH(OH)CH3 H H CN 2 Compd. R2 R1 R3 R4 R5 n No.

.703 H CH=CHCH3 H H CI 0 .704 H CH=CHCH3 H H F 0 .705 H CH=CHCH3 H H Br 0 .706 H CH=CHCH3 H H SO2Me 0 .707 H CH=CHCH3 H H SMe 0 .708 H CH=CHCH3 H H SO2NMe2 0 .709 H CH=CHCH3 H H CF3 0 .710 H CH=CHCH3 H H CH3 0 .711 H CH=CHCH3 H H CH(CH3)2 O .712 H CH=CHCH3 H H NO2 0 .713 H CH=CHCH3 H H OCH3 0 .714 H CH=CHCH3 H H OCF2CF3 0 .715 H CH=CHCH3 H H CN 0 .716 H CH=CHCH3 H H Cl 1 .717 H CH=CHCH3 H H F 1 .718 H CH=CHCH3 H H Br 1 .719 H CH=CHCH3 H H SO2Me 1 .720 H CH=CHCH3 H H SMe 1 .721 H CH=CHCH3 H H SO2NMe2 1 .722 H CH=CHCH3 H H CF3 1 .723 H CH=CHCH3 H H CH3 1 .724 H CH=CHCH3 H H CH(CH3)2 1 .725 H CH=CHCH3 H H NO2 1 .726 H CH=CHCH3 H H OCH3 1 .727 H CH=CHCH3 H H OCF2CF3 1 .728 H CH=CHCH3 H H CN 1 .729 H CH=CHCW3 H H Cl 2 .730 H CH=CHCH3 H H F 2 .731 H CH=CHCH3 H H Br 2 .732 H CH=CHCH3 H H SO2Me 2 .733 H CH=CHCH3 H H SMe 2 Compd. R2 R1 R3 R4 R5 n No.

.734 H CH=CHCH3 H H SO2NMe2 2 .735 H CH=CHCH3 H H CF3 2 .736 H CH=CHCH3 H H CH3 2 .737 H CH=CHCH3 H H CH(CH3)2 2 .738 H CH=CHCH3 H H NO2 2 .739 H CH=CHCH3 H H OCH3 2 .740 H CH=CHCH3 H H OCF2CF3 2 .741 H CH=CHCH3 H H CN 2 .742 H CH=CHCO2CH3 H H Cl 0 .743 H CH=CHCO2CH3 H H F 0 .744 H CH=CHCO2CH3 H H Br 0 .745 H CH=CHCO2CH3 H H SO2Me 0 .746 H CH=CHCO2CH3 H H SMe 0 .747 H CH=CHCO2CH3 H H SO2NMe2 0 .748 H CH=CHCO2CH3 H H CF3 0 .749 H CH=CHCO2CH3 H H CH3 0 .750 H CH=CHCO2CH3 H H CH(CH3)2 O .751 H CH=CHCO2CH3 H H NO2 0 .752 H CH=CHCO2CH3 H H OCH3 0 .753 H CH=CHCO2CH3 H H OCF2CF3 0 .754 H CH=CHCO2CH3 H H CN 0 .755 H CH=CHCO2CH3 H H CI 1 .756 H CH=CHCO2CH3 H H F 1 .757 H CH=CHC02CH3 H H Br 1 .758 H CH=CHCO2CH3 H H SO2Me 1 .759 H CH=CHCO2CH3 H H SMe 1 .760 H CH=CHCO2CH3 H H SO2NMe2 1 .761 H CH=CHCO2CH3 H H CF3 1 .762 H CH=CHCO2CH3 H H CH3 1 .763 H CH=CHCO2CH3 H H CH(CH3)2 1 .764 H CH=CHCO2CH3 H H NO2 1 Compd. R2 R1 R3 R4 R5 n No.

.765 H CH=CHCO2CH3 H H OCH3 1 .766 H CH=CHCO2CH3 H H OCF2CF3 1 .767 H CH=CHCO2CH3 H H CN 1 .768 H CH=CHCO2CH3 H H Cl 2 .769 H CH=CHCO2CH3 H H F 2 .770 H CH=CHCO2CH3 H H Br 2 .771 H CH=CHCO2CH3 H H SO2Me 2 .772 H CH=CHCO2CH3 H H SMe 2 .773 H CH=CHCO2CH3 H H SO2NMe2 2 .774 H CH=CHCO2CH3 H H CF3 2 .775 H CH=CHCO2CH3 H H CH3 2 .776 H CH=CHCO2CH3 H H CH(CH3)2 2 .777 H CH=CHCO2CH3 H H NO2 2 .778 H CH=CHCO2CH3 H H OCH3 2 .779 H CH=CHCO2CH3 H H OCF2CF3 2 .780 H CH=CHCO2CH3 H H CN 2 .781 CH3 CH3 H H Cl 0 .782 CH3 CH3 H H F 0 .783 CH3 CH3 H H Br 0 .784 CH3 CH3 H H SO2Me 0 .785 CH3 CH3 H H SMe 0 .786 CH3 CH3 H H SO2NMe2 0 .787 CH3 CH3 H H CF3 0 .788 CH3 CH3 H H CH3 0 .789 CH3 CH3 H H CH(CH3)2 O .790 CH3 CH3 H H NO2 0 .791 CH3 CH3 H H OCH3 0 .792 CH3 CH3 H H OCF2CF3 0 .793 CH3 CH3 H H CN 0 .794 CH3 CH3 H H CI 1 .795 CH3 CH3 H H F 1 Compd. R2 R1 R3 R4 R5 n No.

.796 CH3 CH3 H H Br 1 .797 CH3 CH3 H H SO2Me .798 CH3 CH3 H H SMe 1 .799 CH3 CH3 H H SO2NMe2 1 .800 CH3 CH3 H H CF3 1 .801 CH3 CH3 H H CH3 1 .802 CH3 CH3 H H CH(CH3)2 1 .803 CH3 CH3 H H NO2 1 .804 CH3 CH3 H H OCH3 1 .805 CH3 CH3 H H OCF2CF3 1 .806 CH3 CH3 H H CN 1 .807 CH3 CH3 H H CI 2 .808 CH3 CH3 H H F 2 .809 CH3 CH3 H H Br 2 .810 CH3 CH3 H H SO2Me 2 .811 CH3 CH3 H H SMe 2 .812 CH3 CH3 H H SO2NMe2 2 .813 CH3 CH3 H H CF3 2 .814 CH3 CH3 H H CH3 2 .815 CH3 CH3 H H CH(CH3)2 2 .816 CH3 CH3 H H NO2 2 .817 CH3 CH3 H H OCH3 2 .818 CH3 CH3 H H OCF2CF3 2 .819 CH3 CH3 H H CN 2 Table 7: Compounds of formula II Compd. R2 R1 R3 R4 R5 n n2 Phys. data No.

7.001 H CH3 H H Cl 0 0 7.002 H CH3 H H F 0 0 7.003 H CH3 H H Br 0 0 7.004 H CH3 H H SO2Me 0 0 7.005 H CH3 H H SMe 0 0 7.006 H CH3 H H SO2NMe2 0 0 7.007 H CH3 H H CF3 0 0 7.008 H CH3 H H CH3 0 0 7.009 H CH3 H H CH(CH3)2 0 0 7.010 H CH3 H H NO2 0 0 7.011 H CH3 H H OCH3 0 0 7.012 H CH3 H H OCF2CF3 0 0 7.013 H CH3 H H CN 0 0 7.014 H CH3 H H Cl 1 0 7.015 H CH3 H H F 1 0 7.016 H CH3 H H Br 1 0 7.017 H CH3 H H SO2Me 1 0 7.018 H CH3 H H SMe 1 0 7.019 H CH3 H H SO2NMe2 1 0 7.020 H CH3 H H CF3 1 0 7.021 H CH3 H H CH3 1 0 7.022 H CH3 H H CH(CH3)2 1 0 7.023 H CH3 H H NO2 1 0 7.024 H CH3 H H OCH3 1 0 7.025 H CH3 H H OCF2CF3 1 0 Compd. R2 R1 R3 R4 R5 n n2 Phys. data No.

7.026 H CH3 H H CN 1 0 7.027 H CH3 H H Cl 2 0 129-130°C 7.028 H CH3 H H F 2 0 7.029 H CH3 H H Br 2 0 7.030 H CH3 H H SO2Me 2 0 7.031 H CH3 H H SMe 2 0 7.032 H CH3 H H SO2NMe2 2 0 7.033 H CH3 H H CF3 2 0 7.034 H CH3 H H CH3 2 0 7.035 H CH3 H H CH(CH3)2 2 0 7.036 H CH3 H H NO2 2 0 7.037 H CH3 H H OCH3 2 0 7.038 H CH3 H H OCF2CF3 2 0 7.039 H CH3 H H CN 2 0 7.040 H CH3 H H CI 0 0 7.041 H CH3 H H F 0 0 7.042 H CH3 H H Br 0 0 7.043 H CH3 H H SO2Me 0 0 7.044 H CH3 H H SMe 0 0 7.045 H CH3 H H SO2NMe2 0 0 7.046 H CH3 H H CF3 0 0 7.047 H CH3 H H CH3 0 0 7.048 H CH3 H H CH(CH3)2 O 0 7.049 H CH3 H H NO2 0 0 7.050 H CH3 H H OCH3 0 0 7.051 H CH3 H H OCF2CF3 0 0 7.052 H CH3 H H CN 0 0 7.053 H CH3 H H Cl 1 0 7.054 H CH3 H H F 1 0 7.055 H CH3 H H Br 1 0 7.056 H CH3 H H SO2Me 1 0 7.057 H CH3 H H SMe 1 0 Compd. R2 R1 R3 R4 R5 n n2 Phys. data No.

7.058 H CH3 H H SO2NMe2 1 0 7.059 H CH3 H H CF3 1 0 7.060 H CH3 H H CH3 1 0 7.061 H CH3 H H CH(CH3)2 1 0 7.062 H CH3 H H NO2 1 0 7.063 H CH3 H H OCH3 1 0 7.064 H CH3 H H OCF2CF3 1 0 7.065 H CH3 H H CN 1 0 7.066 H CH3 H H Cl 2 0 7.067 H CH3 H H F 2 0 7.068 H CH3 H H Br 2 0 7.069 H CH3 H H SO2Me 2 0 7.070 H CH3 H H SMe 2 0 7.071 H CH3 H H SO2NMe2 2 0 7.072 H CH3 H H CF3 2 0 7.073 H CH3 H H CH3 2 0 7.074 H CH3 H H CH(CH3)2 2 0 7.075 H CH3 H H NO2 2 0 7.076 H CH3 H H OCH3 2 0 7.077 H CH3 H H OCF2CF3 2 0 7.078 H CH3 H H CN 2 0 7.079 H CH3 H H Cl 0 1 7.080 H CH3 H H F 0 1 7.081 H CH3 H H Br 0 1 7.082 H CH3 H H SO2Me 0 1 7.083 H CH3 H H SMe 0 1 7.084 H CH3 H H SO2NMe2 0 1 7.085 H CH3 H H CF3 0 1 7.086 H CH3 H H CH3 0 1 7.087 H CH3 H H CH(CH3)2 0 1 7.088 H CH3 H H NO2 0 1 7.089 H CH3 H H OCH3 0 1 Compd. R2 R1 B3 R4 R5 n n2 Phys. data No.

7.090 H CH3 H H OCF2CF3 0 1 7.091 H CH3 H H CN O 1 7.092 H CH3 H H Cl 1 1 7.093 H CH3 H H F 1 1 7.094 H CH3 H H Br 1 1 7.095 H CH3 H H SO2Me 1 1 7.096 H CH3 H H SMe 1 1 7.097 H CH3 H H SO2NMe2 1 1 7.098 H CH3 H H CF3 1 1 7.099 H CH3 H H CH3 1 1 7.100 H CH3 H H CH(CH3)2 1 1 7.101 H CH3 H H NO2 1 1 7.102 H CH3 H H OCH3 1 1 7.103 H CH3 H H OCF2CF3 1 1 7.104 H CH3 H H CN 1 1 7.105 H CH3 H H Cl 2 1 7.106 H CH3 H H F 2 1 7.107 H CH3 H H Br 2 1 7.108 H CH3 H H SO2Me 2 1 7.109 H CH3 H H SMe 2 1 7.110 H CH3 H H SO2NMe2 2 1 7.111 H CH3 H H CF3 2 1 7.112 H CH3 H H CH3 2 1 7.113 H CH3 H H CH(CH3)2 2 1 7.114 H CH3 H H NO2 2 1 7.115 H CH3 H H OCH3 2 1 7.116 H CH3 H H OCF2CF3 2 1 7.117 H CH3 H H CN 2 1 7.118 H CH3 H H Cl 0 2 7.119 H CH3 H H F 0 2 7.120 H CH3 H H Br 0 2 7.121 H CH3 H H SO2Me 0 2 Compd. R2 R1 R3 R4 R5 n n2 Phys. data No.

7.122 H CH3 H H SMe 0 2 7.123 H CH3 H H SO2NMe2 0 2 7.124 H CH3 H H CF3 0 2 7.125 H CH3 H H CH3 0 2 7.126 H CH3 H H CH(CH3)2 0 2 7.127 H CH3 H H NO2 0 2 7.128 H CH3 H H OCH3 0 2 7.129 H CH3 H H OCF2CF3 0 2 7.130 H CH3 H H CN 0 2 7.131 H CH3 H H Cl 1 2 7.132 H CH3 H H F 1 2 7.133 H CH3 H H Br 1 2 7.134 H CH3 H H SO2Me 1 2 7.135 H CH3 H H SMe 1 2 7.136 H CH3 H H SO2NMe2 1 2 7.137 H CH3 H H CF3 1 2 7.138 H CH3 H H CH3 1 2 7.139 H CH3 H H CH(CH3)2 1 2 7.140 H CH3 H H NO2 1 2 7.141 H CH3 H H OCH3 1 2 7.142 H CH3 H H OCF2CF3 1 2 7.143 H CH3 H H CN 1 2 7.144 H CH3 H H Cl 2 2 7.145 H CH3 H H F 2 2 7.146 H CH3 H H Br 2 2 7.147 H CH3 H H SO2Me 2 2 7.148 H CH3 H H SMe 2 2 7.149 H CH3 H H SO2NMe2 2 2 7.150 H CH3 H H CF3 2 2 7.151 H CH3 H H CH3 2 2 7.152 H CH3 H H CH(CH3)2 2 2 7.153 H CH3 H H NO2 2 2 Compd. R2 R1 R3 R4 R5 n n2 Phys. data No.

7.154 H CH3 H H OCH3 2 2 7.155 H CH3 H H OCF2CF3 2 2 7.156 H CH3 H H CN 2 2 7.157 CH3 CH3 H H Cl 0 0 7.158 CH3 CH3 H H F 0 0 7.159 CH3 CH3 H H Br 0 0 7.160 CH3 CH3 H H SO2Me 0 0 7.161 CH3 CH3 H H SMe 0 0 7.162 CH3 CH3 H H SO2NMe2 0 0 7.163 CH3 CH3 H H CF3 0 0 7.164 CH3 CH3 H H CH3 0 0 7.165 CH3 CH3 H H CH(CH3)2 O 0 7.166 CH3 CH3 H H NO2 0 0 7.167 CH3 CH3 H H OCH3 0 0 7.168 CH3 CH3 H H OCF2CF3 0 0 7.169 CH3 CH3 H H CN 0 0 7.170 CH3 CH3 H H CI 1 0 7.171 CH3 CH3 H H F 1 0 7.172 CH3 CH3 H H Br 1 0 7.173 CH3 CH3 H H SO2Me 1 0 7.174 CH3 CH3 H H SMe 1 0 7.175 CH3 CH3 H H SO2NMe2 1 0 7.176 CH3 CH3 H H CF3 1 0 7.177 CH3 CH3 H H CH3 1 0 7.178 CH3 CH3 H H CH(CH3)2 1 0 7.179 CH3 CH3 H H NO2 1 0 7.180 CH3 CH3 H H OCH3 1 0 7.181 CH3 CH3 H H OCF2CF3 1 0 7.182 CH3 CH3 H H CN 1 0 7.183 CH3 CH3 H H Cl 2 0 7.184 CH3 CH3 H H F 2 0 7.185 CH3 CH3 H H Br 2 0 Compd. R2 R1 R3 R4 R5 n n2 Phys. data No.

7.186 CH3 CH3 H H SO2Me 2 0 7.187 CH3 CH3 H H SMe 2 0 7.188 CH3 CH3 H H SO2NMe2 2 0 7.189 CH3 CH3 H H CF3 2 0 7.190 CH3 CH3 H H CH3 2 0 7.191 CH3 CH3 H H CH(CH3)2 2 0 7.192 CH3 CH3 H H NO2 2 0 7.193 CH3 CH3 H H OCH3 2 0 7.194 CH3 CH3 H H OCF2CF3 2 0 7.195 CH3 CH3 H H CN 2 0 Table 8: A further group of compounds of formula I corresponds to general formula Im wherein the meanings of the corresponding substituents R1 to R5 and n are given in Table B, so that 78 specific compounds of formula Im are disclosed.

Table 9: A further group of compounds of formula I corresponds to general formula In wherein the meanings of the corresponding substituents R1 to R5 and n are given in Table B, so that 78 specific compounds of formula In are disclosed.

Table 10: A further group of compounds of formula i corresponds to general formula lo wherein the meanings of the corresponding substituents R1 to R5 and n are given in Table B, so that 78 specific compounds of formula lo are disclosed.

Table 11: A further group of compounds of formula I corresponds to general formula Ip wherein the meanings of the corresponding substituents R1 to R5 and n are given in Table B, so that 78 specific compounds of formula Ip are disclosed.

Table B Compd. R2 R1 R3 R4 R5 n No.

.001 H CH3 H H Cl 0 .002 H CH3 H H F 0 .003 H CH3 H H Br 0 .004 H CH3 H H SO2Me 0 .005 H CH3 H H SMe 0 .006 H CH3 H H SO2NMe2 0 .007 H CH3 H H CF3 0 .008 H CH3 H H CH3 0 .009 H CH3 H H CH(CH3)2 O .010 H CH3 H H NO2 0 .011 H CH3 H H OCH3 0 .012 H CH3 H H OCF2CF3 0 Compd. R2 R1 R3 R4 R5 n No.

.013 H CH3 H H CN 0 .014 H CH3 H H Cl 1 .015 H CH3 H H F 1 .016 H CH3 H H Br 1 .017 H CH3 H H SO2Me 1 .018 H CH3 H H SMe 1 .019 H CH3 H H SO2NMe2 1 .020 H CH3 H H CF3 1 .021 H CH3 H H CH3 1 .022 H CH3 H H CH(CH3)2 1 .023 H CH3 H H NO2 1 .024 H CH3 H H OCH3 1 .025 H CH3 H H OCF2CF3 1 .026 H CH3 H H CN 1 .027 H CH3 H H Cl 2 .028 H CH3 H H F 2 .029 H CH3 H H Br 2 .030 H CH3 H H SO2Me 2 .031 H CH3 H H SMe 2 .032 H CH3 H H SO2NMe2 2 .033 H CH3 H H CF3 2 .034 H CH3 H H CH3 2 .035 H CH3 H H CH(CH3)2 2 .036 H CH3 H H NO2 2 .037 H CH3 H H OCH3 2 .038 H CH3 H H OCF2CF3 2 .039 H CH3 H H CN 2 .040 CH3 CH3 H H Cl 0 .041 CH3 CH3 H H F 0 .042 CH3 CH3 H H Br 0 .043 CH3 CH3 H H SO2Me 0 .044 CH3 CH3 H H SMe 0 Compd. R2 R1 R3 R4 R5 n No.

.045 CH3 CH3 H H SO2NMe2 0 .046 CH3 CH3 H H CF3 0 .047 CH3 CH3 H H CH3 0 .048 CH3 CH3 H H CH(CH3)2 O .049 CH3 CH3 H H NO2 0 .050 CH3 CH3 H H OCH3 0 .051 CH3 CH3 H H OCF2CF3 0 .052 CH3 CH3 H H CN 0 .053 CH3 CH3 H H Cl 1 .054 CH3 CH3 H H F 1 .055 CH3 CH3 H H Br 1 .056 CH3 CH3 H H SO2Me .057 CH3 CH3 H H SMe 1 .058 CH3 CH3 H H SO2NMe2 1 .059 CH3 CH3 H H CF3 1 .060 CH3 CH3 H H CH3 .061 CH3 CH3 H H CH(CH3)2 1 .062 CH3 CH3 H H NO2 1 .063 CH3 CH3 H H OCH3 1 .064 CH3 CH3 H H OCF2CF3 1 .065 CH3 CH3 H H CN 1 .066 CH3 CH3 H H Cl 2 .067 CH3 CH3 H H F 2 .068 CH3 CH3 H H Br 2 .069 CH3 CH3 H H SO2Me 2 .070 CH3 CH3 H H SMe 2 .071 CH3 CH3 H H SO2NMe2 2 .072 CH3 CH3 H H CF3 2 .073 CH3 CH3 H H CH3 2 .074 CH3 CH3 H H CH(CH3)2 2 .075 CH3 CH3 H H NO2 2 .076 CH3 CH3 H H OCH3 2 Compd. R2 R1 R3 R4 R5 n No.

.077 CH3 CH3 H H OCF2CF3 2 .078 CH3 CH3 H H CN 2 Table 12: Compounds of formula lq Compd. R6 (C3) R7 R6 (C5) R18 n Phys. data No.

12.001 CH3 CH3 H H 0 12.002 CH3 CH3 CH3 H 0 12.003 CH3 CH3 CH=CH2 H 0 12.004 CH3 CH3 Br H 0 12.005 CH3 CH3 SMe H 0 12.006 CH3 CH3 H H 1 12.007 CH3 CH3 CH3 H 1 12.008 CH3 CH3 CH=CH2 H 1 12.009 CH3 CH3 Br H 1 12.01 CH3 CH3 SMe H 1 12.011 CH3 CH3 H H 2 159-161°C 12.012 CH3 CH3 CH3 H 2 157-159°CF 12.013 CH3 CH3 CH=CH2 H 2 12.014 CH3 CH3 Br H 2 12.015 CH3 CH3 SMe H 2 12.016 CH3 CH3 CH3 CH3 0 12.017 CH3 CH3 CH=CH2 CH3 0 12.018 CH3 CH3 Br CH3 0 Compd. R6 (C3) R7 R6 (C5) Ria n Phys. data No.

12.019 CH3 CH3 SMe CH3 0 12.02 CH3 CH3 H CH3 1 12.021 CH3 CH3 CH3 CH3 1 12.022 CH3 CH3 CH=CH2 CH3 1 12.023 CH3 CH3 Br CH3 1 12.024 CH3 CH3 SMe CHO 1 12.025 CH3 CH3 H CH3 2 12.026 CH3 CH3 CH3 CH3 2 12.027 CH3 CH3 CH=CH2 CH3 2 12.028 CH3 CH3 Br CH3 2 12.029 CH3 CH3 SMe CH3 2 'R6 (C3)' in Table 12 above means that the substituent R6 is bonded to carbon atom 3 in the compound of formula lq; and accordingly 'R6 (C5)' means that the substituent R6 is bonded to carbon atom 5 in the compound of formula lq.

Table 13: Compounds of formula Ir Compd. R6 R6 R7 R7 Ria n Phys. data No.

13.001 H H H H CH3 0 viscous oil 13.002 H H H H CF3 0 13.003 H H H H CO2CH2CH3 0 viscous oil 13.004 H H H H CH3 1 13.005 H H H H CF3 1 13.006 H H H H CO2CH2CH3 1 Compd. R6 R6 R7 R7 R18 n Phys. data No.

13.007 H H H H CH3 2 129-132°C 13.008 H H H H CF3 2 13.009 H H H H CO2CH2CH3 2 viscous oil 13.010 CH3 H H H H 0 13.011 CH3 H H H CH3 0 13.012 CH3 H H H CF3 0 13.013 CH3 H H H CO2CH2CH3 0 13.014 CH3 H H H H 1 13.015 CH3 H H H CH3 1 13.016 CH3 H H H CF3 1 13.017 CH3 H H H CO2CH2CH3 1 13.018 CH3 H H H H 2 13.019 CH3 H H H CH3 2 13.020 CH3 H H H CF3 2 13.021 CH3 H H H CO2CH2CH3 2 13.022 CH3 H CH3 H H 0 139-140°C 13.023 CH3 H CH3 H CH3 0 13.024 CH3 H CH3 H CF3 0 13.025 CH3 H CH3 H CO2CH2CH3 0 13.026 CH3 H CH3 H H 1 13.027 CH3 H CH3 H CH3 1 13.028 CH3 H CH3 H CF3 1 13.029 CH3 H CH3 H CO2CH2CH3 1 13.030 CH3 H CH3 H H 2 179-180°C 13.031 CH3 H CH3 H CH3 2 13.032 CH3 H CH3 H CF3 2 13.033 CH3 H CH3 H CO2CH2CH3 2 13.034 CH3 CH3 CH3 H H 0 viscous oil 13.035 CH3 CH3 CH3 H CH3 0 13.036 CH3 CH3 CH3 H CF3 0 13.037 CH3 CH3 CH3 H CO2CH2CH3 0 13.038 CH3 CH3 CH3 H H 1 amorphous Compd. R6 R6 R7 R7 Ria n Phys. data No.

13.039 CH3 CH3 CH3 H CH3 1 13.040 CH3 CH3 CH3 H CF3 1 13.041 CH3 CH3 CH3 H CO2CH2CH3 1 13.042 CH3 CH3 CH3 H H 2 resin 13.043 CH3 CH3 CH3 H CH3 2 13.044 CH3 CH3 CH3 H CF3 2 13.045 CH3 CH3 CH3 H CO2CH2CH3 2 13.046 CH3 CH3 CH3 CH3 H 0 13.047 CH3 CH3 CH3 CH3 CH3 0 13.048 CH3 CH3 CH3 CH3 CF3 0 13.049 CH3 CH3 CH3 CH3 CO2CH2CH3 0 13.050 CH3 CH3 CH3 CH3 H 1 13.051 CH3 CH3 CH3 CH3 CH3 1 13.052 CH3 CH3 CH3 CH3 CF3 1 13.053 CH3 CH3 CH3 CH3 CO2CH2CH3 1 13.054 CH3 CH3 CH3 CH3 H 2 13.055 CH3 CH3 CH3 CH3 CH3 2 13.056 CH3 CH3 CH3 CH3 CF3 2 13.057 CH3 CH3 CH3 CH3 CO2CH2CH3 2 13.058 SCH3 H CH3 H H 0 125-128°C 13.059 SO2CH3 H CH3 H H 0 viscous oil 13.060 SCH3 H CH3 H CH3 0 13.061 SCH3 H CH3 H CF3 0 13.062 SCH3 H CH3 H CO2CH2H3 0 13.063 SCH3 H CH3 H H 1 13.064 SCH3 H CH3 H CH3 1 13.065 SCH3 H CH3 H CF3 1 13.066 SCH3 H CH3 H CO2CH2CH3 1 13.067 SCH3 H CH3 H H 2 13.068 SCH3 H CH3 H CH3 2 13.069 SCH3 H CH3 H CF3 2 13.070 SCH3 H CH3 H CO2CH2CH3 2 Compd. R6 R6 R7 R7 R18 n Phys. data No.

13.071 SCH3 CH3 CH3 H H 0 111-113°C 13.072 SCH3 CH3 CH3 H CH3 0 13.073 SCH3 CH3 CH3 H CF3 0 13.074 SCH3 CH3 CH3 H CO2CH2CH3 0 13.075 SCH3 CH3 CH3 H H 1 13.076 SCH3 CH3 CH3 H CH3 1 13.077 SCH3 CH3 CH3 H CF3 1 13.078 SCH3 CH3 CH3 H CO2CH2CH3 1 13.079 SCH3 CH3 CH3 H H 2 resin 13.080 SO2CH3 CH3 CH3 H H 2 244-246°C 13.081 SCH3 CH3 CH3 H CH3 2 13.082 SCH3 CH3 CH3 H CF3 2 viscous oil (E isomer) 13.083 SCH3 CH3 CH3 H CF3 2 viscous oil (Z isomer) 13.084 SCH3 CH3 CH3 H CO2CH2CH3 2 13.085 SCH3 H CH3 CH3 H 0 13.086 SCH3 H CH3 CH3 CH3 0 13.087 SCH3 H CH3 CH3 CF3 0 13.088 SCH3 H CH3 CH3 CO2CH2CH3 0 13.089 SCH3 H CH3 CH3 H 1 13.090 SCH3 H CH3 CH3 CH3 1 13.091 SCH3 H CH3 CH3 CF3 1 13.092 SCH3 H CH3 CH3 CO2CH2CH3 1 13.093 SCH3 H CH3 CH3 H 2 13.094 SCH3 H CH3 CH3 CH3 2 13.095 SCH3 H CH3 CH3 CF3 2 13.096 SCH3 H CH3 CH3 CO2CH2CH3 2 13.097 SCH3 CH3 CH3 CH3 H 0 13.098 SCH3 CH3 CH3 CH3 CH3 0 13.099 SCH3 CH3 CH3 CH3 CF3 0 13.100 SCH3 CH3 CH3 CH3 CO2CH2CH3 0 13.101 SCH3 CH3 CH3 CH3 H 1 13.102 SCH3 CH3 CH3 CH3 CH3 1 Compd. R6 R6 R7 R7 Ria n Phys. data No.

13.103 SCH3 CH3 CH3 CH3 CF3 1 13.104 SCH3 CH3 CH3 CH3 CO2CH2CH3 1 13.105 SCH3 CH3 CH3 CH3 H 2 13.106 SCH3 CH3 CH3 CH3 CH3 2 13.107 SCH3 CH3 CH3 CH3 CF3 2 13.108 SCH3 CH3 CH3 CH3 CO2CH2CH3 2 13.109 SCH3 SCH3 H H H 0 13.110 SCH3 SCH3 H H CH3 0 13.111 SCH3 SCH3 H H CF3 0 13.112 SCH3 SCH3 H H CO2CH2CH3 0 13.113 SCH3 SCH3 H H H 1 13.114 SCH3 SCH3 H H CH3 1 13.115 SCH3 SCH3 H H CF3 1 13.116 SCH3 SCH3 H H CO2CH2CH3 1 13.117 SCH3 SCH3 H H H 2 13.118 SCH3 SCH3 H H CH3 2 13.119 SCH3 SCH3 H H CF3 2 13.120 SCH3 SCH3 H H CO2CH2CH3 2 13.121 SCH3 SCH3 CH3 CH3 H 0 13.122 SCH3 SCH3 CH3 CH3 CH3 0 13.123 SCH3 SCH3 CH3 CH3 CF3 0 13.124 SCH3 SCH3 CH3 CH3 CO2CH2CH3 0 13.125 SCH3 SCH3 CH3 CH3 H 1 13.126 SCH3 SCH3 CH3 CH3 CH3 1 13.127 SCH3 SCH3 CH3 CH3 CF3 1 13.128 SCH3 SCH3 CH3 CH3 CO2CH2CH3 1 13.129 SCH3 SCH3 CH3 CH3 H 2 128-130°C (meso form) 13.130 SCH3 SCH3 CH3 CH3 H 2 189-192°C (E isomer) 13.131 SCH3 SCH3 CH3 CH3 CH3 2 13.132 SCH3 SCH3 CH3 CH3 CF3 2 13.133 SCH3 SCH3 CH3 CH3 CO2CH2CH3 2 13.134 OCH3 H H H H 0 Compd. R6 R6 R7 R7 Ria n Phys. data No.

13.135 OCH3 H H H CH3 0 13.136 OCH3 H H H CF3 0 13.137 OCH3 H H H CO2CH2CH3 0 13.138 OCH3 H H H H 1 13.139 OCH3 H H H CH3 1 13.140 OCH3 H H H CF3 1 13.141 OCH3 H H H CO2CH2CH3 1 13.142 OCH3 H H H H 2 13.143 OCH3 H H H CH3 2 13.144 OCH3 H H H CF3 2 13.145 OCH3 H H H CO2CH2CH3 2 13.146 OCH3 H CH3 H H 0 13.147 OCH3 H CH3 H CH3 0 13.148 OCH3 H CH3 H CF3 0 13.149 OCH3 H CH3 H CO2CH2CH3 0 13.150 OCH3 H CH3 H H 1 13.151 OCH3 H CH3 H CH3 1 13.152 OCH3 H CH3 H CF3 1 13.153 OCH3 H CH3 H CO2CH2CH3 1 13.154 OCH3 H CH3 H H 2 13.155 OCH3 H CH3 H CH3 2 13.156 OCH3 H CH3 H CF3 2 13.157 OCH3 H CH3 H CO2CH2CH3 2 13.158 OCH3 CH3 CH3 H H 0 resin (E isomer) 13.159 OCH3 CH3 CH3 H H 0 104-105°C (Z isomer) 13.160 OCH3 CH3 CH3 H CH3 0 13.161 OCH3 CH3 CH3 H CF3 0 13.162 OCH3 CH3 CH3 H CO2CH2CH3 0 13.163 OCH3 CH3 CH3 H H 1 13.164 OCH3 CH3 CH3 H CH3 1 13.165 OCH3 CH3 CH3 H CF3 1 13.166 OCH3 CH3 CH3 H CO2CH2CH3 1 Compd. R6 R6 R7 R7 Ria n Phys. data No.

13.167 OCH3 CH3 CH3 H H 2 resin (Z isomer) 13.168 OCH3 CH3 CH3 H H 2 resin (E isomer) 13.169 OCH3 CH3 CH3 H CH3 2 13.170 OCH3 CH3 CH3 H CF3 2 13.171 OCH3 CH3 CH3 H CO2CH2CH3 2 13.172 OCH3 CH3 CH3 CH3 H 0 13.173 OCH3 CH3 CH3 CH3 CH3 O 13.174 OCH3 CH3 CH3 CH3 CF3 0 13.175 OCH3 CH3 CH3 CH3 CO2CH2CH3 0 13.176 OCH3 CH3 CH3 CH3 H 1 13.177 OCH3 CH3 CH3 CH3 CH3 1 13.178 OCH3 CH3 CH3 CH3 CF3 1 13.179 OCH3 CH3 CH3 CH3 CO2CH2CH3 1 13.180 OCH3 CH3 CH3 CH3 H 2 13.181 OCH3 CH3 CH3 CH3 CH3 2 13.182 OCH3 CH3 CH3 CH3 CF3 2 13.183 OCH3 CH3 CH3 CH3 CO2CH2CH3 2 13.184 OCH3 H OCH3 H H 0 13.185 OCH3 H OCH3 H CH3 0 13.186 OCH3 H OCH3 H CF3 0 13.187 OCH3 H OCH3 H CO2CH2CH3 0 13.188 OCH3 H OCH3 H H 1 13.189 OCH3 H OCH3 H CH3 1 13.190 OCH3 H OCH3 H CF3 1 13.191 OCH3 H OCH3 H CO2CH2CH3 1 13.192 OCH3 H OCH3 H H 2 13.193 OCH3 H OCH3 H CH3 2 13.194 OCH3 H OCH3 H CF3 2 13.195 OCH3 H OCH3 H CO2CH2CH3 2 13.196 OCH3 CH3 OCH3 CH3 H 0 13.197 OCH3 CH3 OCH3 CH3 CH3 0 13.198 OCH3 CH3 OCH3 CH3 CF3 0 Compd. R6 R6 R7 R7 Ria n Phys. data No.

13.199 OCH3 CH3 OCH3 CH3 CO2CH2CH3 0 13.200 OCH3 CH3 OCH3 CH3 H 1 13.201 OCH3 CH3 OCH3 CH3 CH3 1 13.202 OCH3 CH3 OCH3 CH3 CF3 1 13.203 OCH3 CH3 OCH3 CH3 CO2CH2CH3 1 13.204 OCH3 CH3 OCH3 CH3 H 2 13.205 OCH3 CH3 OCH3 CH3 CH3 2 13.206 OCH3 CH3 OCH3 CH3 CF3 2 13.207 OCH3 CH3 OCH3 CH3 CO2CH2CH3 2 13.208 SCH3 CH3 OCH3 H H 0 amorphous 13.209 SCH3 CH3 OCH3 H CH3 0 13.210 SCH3 CH3 OCH3 H CF3 0 13.211 SCH3 CH3 OCH3 H CO2CH2CH3 0 13.212 SCH3 CH3 OCH3 H H 1 13.213 SCH3 CH3 OCH3 H CH3 1 13.214 SCH3 CH3 OCH3 H CF3 1 13.215 SCH3 CH3 OCH3 H CO2CH2CH3 1 13.216 SCH3 CH3 OCH3 H H 2 166-168°C 13.217 SCH3 CH3 OCH3 H CH3 2 13.218 SCH3 CH3 OCH3 H CF3 2 13.219 SCH3 CH3 OCH3 H CO2CH2CH3 2 13.220 SCH3 CH3 OCH3 CH3 H 0 13.221 SCH3 CH3 OCH3 CH3 CH3 0 13.222 SCH3 CH3 OCH3 CH3 CF3 0 13.223 SCH3 CH3 OCH3 CH3 CO2CH2CH3 0 13.224 SCH3 CH3 OCH3 CH3 H 1 13.225 SCH3 CH3 OCH3 CH3 CH3 1 13.226 SCH3 CH3 OCH3 CH3 CF3 1 13.227 SCH3 CH3 OCH3 CH3 CO2CH2CH3 1 13.228 SCH3 CH3 OCH3 CH3 H 2 13.229 SCH3 CH3 OCH3 CH3 CH3 2 13.230 SCH3 CH3 OCH3 CH3 CF3 2 Compd. R6 R6 R7 R7 Ria n Phys. data No.

13.231 SCH3 CH3 OCH3 CH3 CO2CH2CH3 2 13.232 CH3 H CH3 CH2CH=CH2 H 0 13.233 CH3 H CH3 CH2CH=CH2 CH3 0 13.234 CH3 H CH3 CH2CH=CH2 CF3 0 13.235 CH3 H CH3 CH2CH=CH2 CO2CH2CH3 0 13.236 CH3 H CH3 CH2CH=CH2 H 1 13.237 CH3 H CH3 CH2CH=CH2 CH3 1 13.238 CH3 H CH3 CH2CH=CH2 CF3 1 13.239 CH3 H CH3 CH2CH=CH2 CO2CH2CH3 1 13.240 CH3 H CH3 CH2CH=CH2 H 2 viscous oil 13.241 CH3 H CH3 CH2CH=CH2 CH3 2 13.242 CH3 H CH3 CH2CH=CH2 CF3 2 13.243 CH3 H CH3 CH2CCH CO2CH2CH3 2 13.244 CH3 H CH3 CH2CCH H 0 13.245 CH3 H CH3 CH2CCH CH3 0 13.246 CH3 H CH3 CH2CCH CF3 0 13.247 CH3 H CH3 CH2CCH CO2CH2CH3 0 13.248 CH3 H CH3 CH2CCH H 1 13.249 CH3 H CH3 CH2CCH CH3 1 13.250 CH3 H CH3 CH2CCH CF3 1 13.251 CH3 H CH3 CH2CCH CO2CH2CH3 1 13.252 CH3 H CH3 CH2CCH H 2 viscous oil 13.253 CH3 H CH3 CH2CCH CH3 2 13.254 CH3 H CH3 CH2CCH CF3 2 13.255 CH3 H CH3 CH2CCH CO2CH2CH3 2 13.256 CH3 CH3 CH3 CH2CH=CH2 H 0 13.257 CH3 CH3 CH3 CH2CH=CH2 CH3 0 13.258 CH3 CH3 CH3 CH2CH=CH2 CF3 0 13.259 CH3 CH3 CH3 CH2CH=CH2 CO2CH2CH3 0 Compd. R6 R6 R7 R7 Ria n Phys. data No.

13.260 CH3 CH3 CH3 CH2CH=CH2 H 1 13.261 CH3 CH3 CH3 CH2CH=CH2 CH3 1 13.262 CH3 CH3 CH3 CH2CH=CH2 CF3 1 13.263 CH3 CH3 CH3 CH2CH=CH2 CO2CH2CH3 1 13.264 CH3 CH3 CH3 CH2CH=CH2 H 2 13.265 CH3 CH3 CH3 CH2CH=CH2 CH3 2 13.266 CH3 CH3 CH3 CH2GH=CH2 CF3 2 13.267 CH3 CH3 CH3 CH2CCH CO2CH2CH3 2 13.268 CH3 CH3 CH3 CH2CCH H 0 13.269 CH3 CH3 CH3 CH2CCH CH3 0 13.270 CH3 CH3 CH3 CH2CCH CF3 0 13.271 CH3 CH3 CH3 CH2CCH CO2CH2CH3 0 13.272 CH3 CH3 CH3 CH2CCH H 1 13.273 CH3 CH3 CH3 CH2CCH CH3 1 13.274 CH3 CH3 CH3 CH2CCH CF3 1 13.275 CH3 CH3 CH3 CH2CCH CO2CH2CH3 1 13.276 CH3 CH3 CH3 CH2CCH H 2 13.277 CH3 CH3 CH3 CH2CCH CH3 2 13.278 CH3 CH3 CH3 CH2CCH CF3 2 13.279 CH3 CH3 CH3 CH2CCH CO2CH2CH3 2 Table C: Physico-chemical data for prepared compounds in the above-mentioned Tables 1- 6 and A, and also 8-11 and B. The figure before the point indicates the number of the Table, e.g. 1.027 indicates in Table 1 compound No. 027 of Table A, and 11.027 indicates in Table 11 compound No. 027 of Table C. Compd. Physico-chemical data No. 1.001 m.p. 215-218°C 1.002 m.p. 180°C 1.003 m.p. 204-206°C Compd. Physico-chemical data No. 1.005 m.p. 225-226°C 1.008 m.p. 213-216°C 1.016 m.p. 194-196°C 1.027 m.p. 223-225°C 1.029 m.p. 220-230°C 1.030 m.p. 222°C 1.031 m.p. 263-264°C 1.033 m.p. 187-189°C 1.034 m.p. 220-2210C 2.001 m.p. 123-126°C 2.002 m.p. 127-129°C 2.003 m.p. 112-114°C 2.005 m.p. 133-134°C 2.008 m.p. 173-174°C 2.027 m.p. 170-172°C 2.028 m.p. 168-1710C 2.029 m.p. 173-174°C 2.030 m.p. 252°C 2.033 m.p. 132-135°C 2.034 m.p. 206°C 2.807 m.p. 134-135°C 3.027 m.p. 183-184°C 3.029 m.p. 185-186°C 3.033 m.p. 141-144°C 5.027 resin 6.005 resin 6.027 m.p. 194-195°C 6.029 m.p. 189-190°C 9.001 m.p. 129-130°C 9.027 m.p. 178-180°C 10.001 m.p. 191-193°C 10.003 m.p. 192-193°C Compd. Physico-chemical data No. 10.016 m.p. 199-200"C 10.027 m.p. 230-233"C 10.029 m.p. 191-192"C 10.033 m.p. 222-224"C 11.001 m.p.185-188°C 11.027 m.p. 216-218"C 11.040 m.p.117-120°C 11.066 m.p. 213-215"C Examples of specific formulations for compounds of formula I, such as emulsifiable concen- trates, solutions, wettable powders, coated granules, extruder granules, dusts and suspen- sion concentrates, are described on pages 9 to 13 of WO 97/34485.

Biological Examples Example B1: Herbicidal action Drior to emergence of the plants (pre-emergence action) Monocotyledonous and dicotyledonous test plants are sown in standard soil in plastics pots.

Immediately after sowing, the test compounds, in the form of an aqueous suspension or emulsion prepared from a 25 % wettable powder (Example F3, b), as described, for example, in WO 97/34485, or in the form of an emulsion (prepared from a 25 % emulsifiable concentrate (Example F1, c), as described, for example, in WO 97/34485), are applied by spraying in a concentration corresponding to 2000 g of active ingredient/ha (500 litres water/ha). The test plants are then grown in a greenhouse under optimum conditions.

After a test duration of 3 weeks, the test is evaluated in accordance with a scale of nine ratings (1 = total damage, 9 = no action). Ratings of from 1 to 4 (especially from 1 to 3) indicate good to very good herbicidal action.

Test plants: Cyperus, Sinapis, Solanum The compounds according to the invention exhibit good herbicidal action.

Examples of the good herbicidal activity of the compounds of formula I are given in Table B1.

Table B1: Pre-emeraence action: Test plant: Cyperus Sinapis Solanum Conc.

[g a.i./ha] Compound No.

2.001 6 2 2 2000 2.003 1 1 1 2000 2.027 3 2 2 2000 2.029 1 1 1 2000 2.034 3 5 3 2000 2.807 2 2 5 2000 3.027 3 1 1 2000 6.029 3 2 2 2000 9.001 3 2 1 2000 10.001 4 5 3 2000 10.027 3 3 2 2000 11.027 4 4 1 2000 12.012 3 7 3 2000 13.007 2 2 2 2000 13.022 3 2 2 2000 13.030 4 4 2 2000 13.038 3 2 2 2000 The same results are obtained when compounds of formula I are formulated in accordance with Examples F2 to F8, as described, for example, in WO 97/34485.

Example B2: Post-emergence herbicidal action In a greenhouse, monocotyledonous and dicotyledonous test plants are grown in standard soil in plastics pots and at the 4- to 6-leaf stage are sprayed with an aqueous suspension or emulsion of the test compounds of formula I, prepared from a 25 % wettable powder (Example F3, b), as described, for example, in WO 97/34485, or in the form of an emulsion (prepared from a 25 % emulsifiable concentrate (Example F1, c), as described, for example, in WO 97/34485), in a concentration corresponding to 2000 g of active ingredient/ha (500 litres water/ha). The test plants are then grown on in a greenhouse under optimum conditions. After a test duration of about 18 days, the test is evaluated in accordance with a scale of nine ratings (1 = total damage, 9 = no action). Ratings of from 1 to 4 (especially from 1 to 3) indicate good to very good herbicidal action.

Test plants: Setaria, Sinapis, Solanum, Stellaria In this test too, the compounds of formula I exhibit strong herbicidal action.

Examples of the good herbicidal activity of the compounds of formula I are given in Table B2.

Table B2: Post-emeraence action: Test plant: Setaria Sinapis Solanum Stellaria Conc.

[g a.i./ha] Compd. No.

2.001 3 1 2 4 2000 2.002 6 2 1 4 2000 2.003 4 2 2 3 2000 2.005 4 2 2 3 2000 2.008 5 2 2 2 2000 2.027 3 1 2 3 2000 2.028 3 2 2 3 2000 2.029 5 2 2 2 2000 2.030 5 2 2 2 2000 2.034 3 2 2 3 2000 2.807 3 2 1 2 2000 3.027 4 1 1 4 2000 3.029 5 2 2 2 2000 5.027 3 2 1 2 2000 6.005 2 2 2 2 2000 6.027 5 1 4 3 2000 6.029 7 1 1 2 2000 7.027 8 2 2 4 2000 9.001 4 1 1 3 2000 9.027 3 2 2 4 2000 10.001 3 1 1 3 2000 10.003 3 1 2 3 2000 10.016 3 2 3 3 2000 10.027 3 1 2 4 2000 10.029 3 3 2 3 2000 11.001 2 1 2 3 2000 11.027 2 2 2 2 2000 11.040 1 2 2 2 2000 11.066 2 1 2 2 2000 12.012 3 1 1 3 2000 13.001 4 1 1 3 2000 13.007 3 1 2 2 2000 13.022 5 1 1 2 2000 13.030 5 1 1 2 2000 13.034 3 1 1 3 2000 13.038 3 1 1 2 2000 13.042 4 1 1 2 2000 13.058 6 2 2 3 2000 13.059 7 3 2 4 2000 13.071 7 2 1 2 2000 13.079 4 1 1 3 2000 13.080 6 1 1 2 2000 13.158 2 1 1 2 2000 13.159 3 3 3 3 2000 13.167 2 1 1 2 2000 13.168 2 2 2 2 2000 13.216 6 2 4 2 2000 13.240 3 1 2 3 2000 13.252 3 3 2 3 2000 The same results are obtained when compounds of formula I are formulated in accordance with Examples F2 to F8, as described, for example, in WO 97/34485.