Asymmetric dihvdrotriazines as pesticides The invention relates to a compound of formula wherein Xi is R8 ; X2 and X3 are each independently of the other H or R8 ; Ri is unsubstituted or mono-to penta-substituted aryl or heteroaryl, the substituents of the aryl and heteroaryl groups being selected from the group consisting of OH, halogen, CN, NO2, C1-C12alkyl, C3-C8-cycloalkyl, C1-C6alkyl-C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C6alkyl, C1-C12haloalkyl, C3-C8halocycloalkyl, C1-C12alkoxy, C3-C8cyclo-alkoxy, C1-C12haloalkoxy, C3-C8halocycloalkoxy, C1-C12alkylthio, C3-C8cycloalkylthio, C1-C12haloalkylthio, C3-C8halocycloalkylthio, C1-C12 alkylsulfinyl, C3-C8cycloalkyl-sulfinyl, C,-Cl2haloalkylsuffinyl, C3-C8halocycloalkylsulfinyl, <BR> <BR> <BR> Ci-Cl2alkylsulfonyl, C3-C8-cycloalkylsulfonyl, C1-C, 2haloalkylsulfonyl,<BR> <BR> <BR> <BR> <BR> <BR> C3-C8halocycloalkylsulfonyl, C2-Csalkenyl, C2-C8alkynyl, Ci-Cl2alkylcarbonyl, -CH (=NOR4),-C (=NOR4)-Ci-Cl2alkyl, 2,2-difluorobenzo [1, 3] dioxol-5-yl and Rio ; unsubstituted or mono-to penta-substituted phenyl or heteroaryl, the substituents of phenyl and heteroaryl being selected from the group consisting of OH, halogen, CN, N02, C,-C6alkyl, C3-C8cycloalkyl, C3-C8Cycloalkenyl which is unsubstituted or substituted; C1-C12haloalkyl, C3-C8halocycloalkyl, C1-C12alkoxy, C3-C8cycloalkoxy, C1-C12haloalkoxy, C3-C8halocycloalkoxy, C1-C12alkylthio, C3-C8cycloalkylthio, C1-C12- haloalkylthio, C3-C8halocycloalkylthio, C1-Cl2alkylsulfinyl, C3-C8cycloalkylsulfinyl, C1-Cl2haloalkylsulfinyl, C3-C8halocycloalkylsulfinyl, C,-C, 2alkylsulfonyl, C3-Cscyclo- alkylsulfonyl, C1-C12haloalkylsulfonyl, C3-C8halocycloalkylsulfonyl, C2-C8alkenyl which is unsubstituted or substituted, C2-C8alkynyl which is unsubstituted or substituted, Ci-Cl2alkylcarbonyl,-CH (=NOR4),-C (=NOR4)-C1-C12alkyl, -CHO, -C(=O)-C1-C12alkyl and Rio ; unsubstituted or mono-to penta-substituted phenoxy; unsubstituted or mono-to penta-substituted phenylthio ; unsubstituted or mono-to penta-substituted phenylamino ; and unsubstituted or mono-to penta-substituted phenyl-(Ct-C6alkyl)-amino ; the substituents of the phenoxy, phenylthio, phenylamino and phenyl-(C1-C6alkyl) amino groups being selected from the group consisting of halogen, CN, NO2, C1-C6-alkyl, C3- Cscycloalkyl, C1-C6haloalkyl, C3-C8halocycloalkyl, Ci-C6alkoxy, C3-C8cyclo-alkoxy, Ci- C6alkylthio, C3-C8cycloalkylthio, C,-C6haloalkylthio and C3-C8halocyclo-alkylthio ; R2 is H, OH, halogen, CN, NO2, C1-C12alkyl, C1-C12alkoxy, C1-C12alkoxy-C1-C6alkyl, C1-C12alkylthio, C1-C12alkylthio-C1-C12alkyl, C3-C8-cycloalkyl, C1-C12haloalkyl, C3-C8- halocycloalkyl, formyl ; or C1-C12alkyl, C1-C12alkoxy or C1-C12alkylthio, each of which is mono-to penta-substituted by CN, N02, aryl, aryloxy,-C (=O) OC1-C12alkyl, -C(=O)O- aryl,-C (=O) Ci-Cl2alkyl, N (R5) 2 or by-S02N (R5) 2, the substituents being selected independently of one another; R3a and R3b are R3 ; R3 is -(C=Y)n-W-R9 ; and either R3a is R3 ; and R3b and R together form a bond; or R3b is R3 ; and R3a and R together form a bond; R4 is Ct-C4alkyl or C3-C6cycloalkyl ; each R5 independently of the other is H, C1-C12alkyl, C3-C8-cycloalkyl, C1-C12haloalkyl, G2-C8-alkenyl, C2-C8alkynyl, aryl-C,-C6alkyl, (CH2) pC (O) R6 or C1-C6alkoxy-C2-C6alkyl ; R6 is H, C1-C12alkyl, C3-C8-cycloalkyl, C1-C12haloalkyl, C1-C12alkoxy, N (R7) 2 or Ci-C6alkoxy- C2-C6alkyl ; each R7 independently of the other is H, C1-C12alkyl, C3-C8-cycloalkyl, C1-C12haloalkyl or aryl- C,-C6alkyl ; R8 is halogen, CN, N02, C1-C12alkyl, C1-C12haloalkyl, C1-C12alkoxy, C3-C8cycloalkyl, C3-C8cycloalkoxy, C1-C12haloalkoxy, C3-C8halocycloalkoxy, C1-C12alkylthio, C3-C8-cycloalkylthio, C1-C12haloalkylthio or C3-C8halocycloalkylthio ; Rg is H, OH, halogen, CN, C1-C12alkyl, C1-C12alkoxy-C1-C12alkyl, C1-C12alkylthio- C1-C12alkyl, C3-C8-cycloalkyl, C1-C12haloalkyl, C1-C12cyanoalkyl, C3-C12alkenyl, C3-Cl2alkinyl, C3-C8halocycloalkyl, phenyl, phenyl-C1-C6alkyl, or phenyl or phenyl- C1-C6alkyl, wherein the phenyl groups are each mono-to tri-substituted by halogen, C1-C12alkyl, C1-C12alkoxy, C1-C12alkylthio, C3-C8-cycloalkyl, C1-C12haloalkyl, C,-C,2haloalkoxy, nitro or by cyano, the substituents being selected independently of one another; RI, and R12 are each independently of the other H or C1-C12alkyl ; the group-A-is a direct bond, C1-C12alkylene, -O-, -O(C1-C12alkylene), -S(O)q-, -S (O) q (Ct-C12alkylene), C2-C8alkenylene, C2-C8alkynylene ;-NR3-or -NR3 (C1-C12alkylene) ; W is a direct bond,-0-,-S-,-SO-,-S02-,-S02-NH-,-NH-or-N (Ci-C4alkyl) ; Y is 0 or S ; Z is O or S; m is1, 2,3 or 4; n is 0, 1 or 2 ; p is 0, 1,2,3,4,5 or 6; and q is 0,1 or 2; where appropriate to E/Z isomers, to mixtures of E/Z isomers and/or tautomers, in each case in free form or in salt form; to a process for the preparation of those compounds and their salts, isomers and tautomers and to the use thereof; to pesticidal compositions, the active ingredient of which is selected from those compounds and their tautomers; and to processes for the preparation of those compositions and to the use thereof, and to intermediates, in free form or in salt form, in the preparation of those compounds, and, where appropriate, their tautomers, in free form or in salt form.

The literature proposes certain tetrahydropyrimidine derivatives in pesticidal compositions.

The biological properties of those known compounds are not, however, fully satisfactory in the area of pest control and there is accordingly a need to provide further compounds having pesticidal properties, especially for the control of insects, that problem being solved according to the invention by the provision of the present compounds of formula (1).

Some of the compounds of formula (I) may be present in the form of tautomers. Accordingly hereinbefore and hereinafter any reference to the compounds of formula (I) should be understood as including also any corresponding tautomers, even when the latter are not specifically mentioned in each case. Examples of such tautomeric forms include, for example : wherein Ri, R2, R3, X1, X2 and X3 are as defined for formula (I). The prepared compounds accordingly are often present in the form of mixtures of isomers and tautomers thereof, in free form or in salt form.

Accordingly hereinbefore and hereinafter any reference to the compounds of formula (I) should be understood as including also corresponding isomers, tautomeric forms of the isomers and, where appropriate, the salts of the isomers and tautomers, even when the latter are not specifically mentioned in each case.

The compounds of formula (I) and, where appropriate, the tautomers thereof can form salts, e. g. acid addition salts. Those salts are formed, for example, with strong inorganic acids, such as mineral acids, e. g. sulfuric acid, a phosphoric acid or a hydrohalic acid, with strong organic carboxylic acids, such as unsubstituted or substituted, for example halo-substituted, C-C4alkanecarboxylic acids, e. g. acetic acid, or saturated or unsaturated dicarboxylic acids, e. g. oxalic, malonic, maleic, fumaric or phthalic acid, or hydroxycarboxylic acids, e. g. ascorbic, lactic, malic, tartaric or citric acid, or benzoic acid, or with organic sulfonic acids, such as unsubstituted or substituted, for example halo-substituted, Cl-C4alkane-or aryl- sulfonic acids, e. g. methanesulfonic or p-toluenesulfonic acid. Furthermore, compounds of formula (I) having at least one acidic group are capable of forming salts with bases. Suitable salts with bases are, for example, metal salts, such as alkali metal or alkaline earth metal salts, e. g. sodium, potassium or magnesium salts, or salts with ammonia or an organic amine, such as morpholine, piperidine, pyrrolidine, a mono-, di-or tri-lower alkylamine, e. g. ethylamine, diethylamine, triethylamine or dimethylpropylamine, or a mono-, di-or tri- hydroxy-lower alkylamine, e. g. mono-, di-or tri-ethanolamine. Where appropriate, corresponding internal salts may also be formed. Preference is given to the free form.

Among the salts of compounds of formula (I) preference is given to agrochemically advantageous salts. Hereinbefore and hereinafter any reference to the free compounds of formula (I) or to their salts should be understood as including also the corresponding salts or the free compounds of formula (I), respectively, as appropriate. The same applies also to tautomers of compounds of formula (I) and salts thereof.

Unless otherwise defined, the general terms used hereinbefore and hereinafter have the following meanings.

Carbon-containing groups and compounds, unless otherwise defined, each contain from 1 up to and including 6 carbon atoms, preferably from 1 up to and including 4 carbon atoms, especially 1 or 2 carbon atoms.

Aryl is phenyl or naphthyl.

Heteroaryl is especially pyridyl, pyrimidyl, s-triazinyl, 1,2,4-triazinyl, thienyl, furanyl, pyrryl, pyrazolyl, imidazolyl, thiazolyl, triazolyl, oxazolyl, thiadiazolyl, oxadiazolyl, benzothienyl, benzofuranyl, benzothiazolyl, indolyl or indazolyl, which are preferably bonded via a carbon atom; preference is given to thienyl, thiazolyl, benzofuranyl, benzothiazolyl or indolyl, especially thienyl, thiazolyl or indolyl, more especially thienyl.

Halogen-as a group per se and as a structural element of other groups and compounds, such as of haloalkyl, haloalkoxy and haloalkylthio-is fluorine, chlorine, bromine or iodine, especially fluorine, chlorine or bromine, more especially fluorine or chlorine.

Alkyl-as a group per se and as a structural element of other groups and compounds, such as of haloalkyl, alkoxy and alkylthio,-is, in each case giving due consideration to the number of carbon atoms present in the group or compound in question, either straight-chain, e. g. methyl, ethyf, propyl, butyl, pentyl, hexyl, heptyl or octyl, or branched, e. g. isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, neopentyl or isohexyl.

Cycloalkyl-as a group perse and as a structural element of other groups and compounds, such as of halocycloalkyl, cycloalkoxy and cycloalkylthio,-is, in each case giving due consideration to the number of carbon atoms present in the group or compound in question, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl.

Alkenyl-as a group per se and as a structural element of other groups and compounds-is, in each case giving due consideration to the number of carbon atoms and conjugated or isolated double bonds present in the group or compound in question, either straight-chain, e. g. allyl, 2-butenyl, 3-pentenyl, 1-hexenyl, 1-heptenyl, 1,3-hexadienyl or 1,3-octadienyl, or branched, e. g. isopropenyl, isobutenyl, isoprenyl, tert-pentenyl, isohexenyl, isoheptenyl or isooctenyl.

Alkynyl-as a group per se and as a structural element of other groups and compounds-is, in each case giving due consideration to the number of carbon atoms and conjugated or isolated double bonds present in the group or compound in question, either straight-chain, e. g. propargyl, 2-butynyl, 3-pentynyl, 1-hexynyl, 1-heptynyl, 3-hexen-1-ynyl or 1,5-hepta- dien-3-ynyl, or branched, e. g. 3-methylbut-1-ynyl, 4-ethylpent-1-ynyl, 4-methylhex-2-ynyl or 2-methylhept-3-ynyl.

Alkylen, alkenylene and alkynylene are straight-chain or branched bridging members, and are especially-CH2-,-CH2-CH2-,-CH2-CH2-CH2-,-CH (CH3)-,-CH2 (CH3) CH2-, -CH2 (CH3) CH2-CH2-,-CH2C (CH3) 2-CH2-,-CH=CH-,-CH2-CH=CH-,-CH2-CH=CH-CH2- ; -C--C-, and-CH2C-C-; especially-CH2-.

Halo-substituted carbon-containing groups and compounds, such as haloalkyl, haloalkoxy or haloalkylthio, may be partially halogenated or per-halogenated, the halogen substituents in the case of poly-halogenation being the same or different. Examples of haloalkyl-as a group per se and as a structural element of other groups and compounds, such as of haloalkoxy or haloalkylthio-are methyl substituted from one to three times by fluorine, chlorine and/or by bromine, such as CHF2 or CF3 ; ethyl substituted from one to five times by fluorine, chlorine and/or by bromine, such as CH2CF3, CF2CF3, CF2CC13, CF2CHC12, CF2CHF2, CF2CFCI2, CF2CHBr2, CF2CHCIF, CF2CHBrF or CCIFCHCIF ; propyl or isopropyl each substituted from one to seven times by fluorine, chlorine and/or by bromine, such as CH2CHBrCH2Br, CF2CHFCF3, CH2CF2CF3 or CH (CF3) 2; butyl or an isomer thereof, substituted from one to nine times by fluorine, chlorine and/or by bromine, such as CF (CF3) CHFCF3 or CH2 (CF2) 2CF3; pentyl or an isomer thereof, substituted from one to eleven times by fluorine, chlorine and/or by bromine, such as CF (CF3) (CHF) 2CF3 or CH2 (CF2) 3CF3 ; and hexyl or an isomer thereof, substituted from one to thirteen times by fluorine, chlorine and/or by bromine, such as (CH2) 4CHBrCH2Br, CF2 (CHF) 4CF3, CH2 (CF2) 4CF3 or C (CF3) 2 (CHF) 2CF3.

Within the context of the present invention preference is given to (1) compounds of formula (I) wherein Ri is unsubstituted or mono-to tri-substituted phenyl, the substituents being selected from the group consisting of OH, halogen, CN, N02, C,-C4alkyl, C3-C6cycloalkyl, CH2-C3-C6cycloalkyl, Ci-C4haloalkyl, <BR> <BR> <BR> <BR> C3-C6halocycloalkyl, C1-C4alkoxy, Cr-C4haloalkoxy, C-C4alkylthio, C1-C4haloalkylthio,<BR> <BR> <BR> <BR> <BR> <BR> C1-C4alkylsulfinyl, C1-C4haloalkylsulfinyl, C1-C4alkylsulfonyl, C1-C4haloalkylsulfonyl, C3-C6alkenyl, C3-C6alkynyl ; unsubstituted or mono-or di-substituted phenyl, the substituents being selected from the group consisting of halogen, CN, NO2, Ci-C4alkyl, C3-C6cycloalkyl, C1-C4haloalkyl, C3-C6halocycloalkyl, C1-C4alkoxy, C3-C6cycloalkoxy, C1-C4haloalkoxy, C3-C6halo-cycloalkoxy, C1-C4alkylthio, C1-C4haloalkylthio, C1-C4alkylsulfinyl, C1-C4haloalkylsulfinyl, C1-C4alkyl- sulfonyl, C1-C4haloalkylsufonyl, C3-C6alkenyl, C3-C6alkynyl, C1-C4alkylcarbonyl, -CH (=NOR4), -C (=NOR4)-C1-C4alkyl,-CHO,-C (=O)-Ci-C4alkyl and Rio ; and unsubstituted or mono-to penta-substituted phenoxy; unsubstituted or mono-to penta-substituted phenylthio ; unsubstituted or mono-to penta-substituted phenylamino ; and unsubstituted or mono-to penta-substituted phenyl- (Ci-C6alkyl)-amino ; the substituents of the phenoxy, phenylthio, phenylamino and phenyl-(Ct-C6alkyl) amino groups being selected from the group consisting of halogen, CN, N02, C1-C4alkyl, C3-C6- <BR> <BR> <BR> cycloalkyl, Ci-C4haloalkyl, C3-C6halocycloalkyl, Ci-C4alkoxy, C3-C6cycloalkoxy, C1-C4alkylthio and Ci-C4haloalkylthio ; Ri is especially unsubstituted or mono-or di-substituted phenyl, the substituents being selected from the group consisting of halogen, CN, NO2, C1-C2alkyl, C3-C6cycloalkyl, C1-C2haloalkyl, C1-C2alkoxy, C1-C2halo- alkoxy, C1-C2alkylthio, C1-C2haloalkylthio, C1-C2alkylsulfinyl, C1-C2haloalkylsulfinyl, C1-C2alkylsulfonyl, C1-C2haloalkylsulfonyl, C3-C4alkenyl and C3-C4alkynyl ; unsubstituted or mono-or di-substituted phenyl, the substituents being selected from the group consisting of fluorine, chlorine, CN, NO2, C1-C2alkyl, C3-C6cycloalkyl, Ci-C2haloalkyl, C3-C6halocycloalkyl, C1-C2alkoxy, C1-C2haloalkoxy, C1-C2alkylthio, C1-C2haloalkylthio, C1-C2alkylsulfinyl, C1-C2haloalkylsulfinyl, C1-C2alkylsulfonyl, C1-C2haloalkylsulfonyl, C3-C4alkenyl, C3-C4alkynyl, C1-C2alkylcarbonyl, -CH (=NOR4),-C (=NOR4)-Ci-C2alkyl,-CHO, -C (=O)-Ct-C2alkyl and Rio ; and unsubstituted or mono-to penta-substituted phenoxy; unsubstituted or mono-to penta-substituted phenylthio ; unsubstituted or mono-to penta-substituted phenylamino ; and unsubstituted or mono-to penta-substituted phenyl-(C1-C6alkyl)-amino ; the substituents of the phenoxy, phenylthio, phenylamino and phenyl- (Ci-C6alkyl) amino groups being selected from the group consisting of fluorine, chlorine, CN, NO2, CH3, cyclo- propyl, CF3, OCF3, OCH3, SCH3 and SCF3 ; R, is very especially mono-substituted phenyl substituted by a mono-or di-substituted phenyl, the substituents on the mono-or di-substituted phenyl being selected from the group consisting of fluorine, chlorine, methyl, cyclopropyl, trifluoromethyl, methoxy, trifluoromethoxy, methylthio and trifluoromethylthio ; more especially wherein Ri is phenyl substituted in the p-position by an unsubstituted or mono-or di-substituted phenyl ; (2) compounds according to (1) of formula (I) wherein R2 is H, OH, halogen, CN, NO2, C1-C6alkyl, C1-C6alkoxy, C1-C6alkoxy-C1-C6alkyl, C1-C6alkylthio, C1-C6alkylthio-C1-C6alkyl, C3-C8cycloalkyl, C1-C6haloalkyl, C3-C8halocycloalkyl, formyl ; or C1-C6alkyl C1-C6alkoxy or C,-C6alkylthio, each of which is mono-to penta-substituted by halogen, CN, N02, aryl, aryloxy,-C (=O) OC1-C6alkyl,-C (=O) O-aryl, aryloxy,-C (=O) C,-C6alkyl, N (R5) 2 or by -S02N (R5) 2, the substituents being selected independently of one another; especially H, OH, halogen, CN, N02, C1-C4alkyl, C1-C4alkoxy, C1-C2alkoxy-C1-C2alkyl, C3-C8cycloalkyl, C1-C4haloalkyl ; or C1-C6alkyl mono-or di-substituted by CN, N02, phenyl or by phenoxy; more especially H, C1-C4alkyl, C,-C4cyanoalkyl, C1-C4nitroalkyl, C3-C8cycloalkyl ; or C1-C2alkyl mono-or di-substituted by phenyl or by phenoxy; especially H, C1-C4alkyl or C1-C2nitroalkyl ; (3) compounds according to (1) or (2) of formula (I) wherein R4 is H, C1-C6alkyl or C3-C8cycloalkyl ; especially methyl, ethyl or cyclopropyl ; (4) compounds according to (1) to (3) of formula (I) wherein each R5 independently of the other is H or C1-C4alkyl ; especially H, methyl or ethyl ; (5) compounds according to (1) to (4) of formula (I) wherein R6 is C1-C4alkyl, C3-C6cycloalkyl, C1-C6alkoxy or N (R7) 2; especially methyl or ethyl ; (6) compounds according to (1) to (5) of formula (I) wherein each R7 independently of the other is H, methyl or ethyl ; (7) compounds according to (1) to (6) of formula (I) wherein Xt is halogen, Ci-C4alkyl, C3-C6cycloalkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylthio or C1-C4haloalkylthio ; especially halogen, C1-C2alkyl, C1-C2haloalkyl, C1-C2alkoxy or Ci-C2- haloalkoxy ; more especially fluorine, chlorine, methyl, trifluoromethyl or methoxy, very especially fluorine or chlorine, especially fluorine; (8) compounds according to (1) to (7) of formula (I) wherein X2 is H, halogen, C1-C4alkyl, C3-C6cycloalkyl,C1-C4haloalkyl, Ci-C4alkoxy, Ci-C4haloalkoxy, Ci-C4alkylthio or C,-C4- haloalkylthio ; especially H, halogen, C1-C2alkyl, C1-C2haloalkyl, C1-C2alkoxy or C1-C2- haloalkoxy ; more especially fluorine, chlorine, methyl, trifluoromethyl or methoxy, especially fluorine or chlorine, very especially fluorine; (9) compounds according to (1) to (8) of formula (I) wherein X3 is H, halogen, C1-C4alkyl, C3-C6cycloalkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylthio or Ci-C4- haloalkylthio ; especially H, halogen, C1-C2alkyl, C1-C2haloalkyl, C1-C2alkoxy or Ci-C2- haloalkoxy ; more especially fluorine, chlorine, methyl, trifluoromethyl or methoxy, especially H, fluorine or chlorine, preferably H; (10) compounds according to (1) to (6) of formula (I) wherein Xi is fluorine or chlorine, X2 is H and X3 is 4-chlorine or 4-fluorine ; especially wherein Xi is chlorine, X2 is H and X3 is 4-fluorine ; (11) compounds according to (1) to (6) of formula (I) wherein Xi is chlorine and X2 and X3 are H; (12) compounds according to (1) to (11) of formula (I) wherein Y is O ; (13) compounds according to (1) to (12) of formula (I) wherein n is 0 ; (14) compounds according to (1) to (12) of formula (I) wherein n is 1; (15) compounds according to (1) to (14) of formula (I) wherein R3a is R3 ; and R3b and R together form a bond; (16) compounds according to (1) to (14) of formula (I) wherein R3b is R3 ; and R3a and R together form a bond; (17) compounds according to (1) to (16) of formula (I) wherein Rg is hydrogen, C1-C4alkyl, C1-C6cycloalkyl, phenyl or phenyl-C,-C6alkyl ; especially hydrogen, C,-C2alkyl, phenyl or benzyl ; (18) compounds according to (1) to (17) of formula (I) wherein W is a direct bond, O, S or NH, especially a direct bond or O ; very especially a direct bond; (19) compounds according to (1) to (18) of formula (I) wherein-A-is a direct bond, C1-C4alkylene, -O-, -O(C1-C4alkylene), -S-, -NR3 or -NR3(C1-C12alkylene) ; especially a direct bond, C1-C2alkylene, -O-, -OCH2- or -NR3 ; more especially a direct bond,-O-,-OCH2-, -C#C-, -CH=CH- or -NH-; very especially-O-or a direct bond; especially a direct bond.

Within the context of the invention, special preference is given to the compounds of formula (I) listed in the Tables and, where appropriate, to their E/Z isomers and mixtures of E/Z isomers, in free form or in salt form.

The invention relates also to a process for the preparation of compounds of formula (I) and, where appropriate, their tautomers, in each case in free form or in salt form, wherein (a) for the preparation of a compound of formula (I) wherein R3 is hydrogen, a compound of formula which is known or can be prepared according to methods known per se and wherein A, Ri and R2 are as defined for formula (I), is reacted with a compound of formula which is known or can be prepared according to methods known per se and wherein Xi, X2 and X3 are as defined for formula (I) and Hal is a halogen atom ; (b) the resulting compound of formula which is known or can be prepared according to methods known per se and wherein X1, X2, X3, A, R1 and R2 are as defined for formula (I), is hydrogenated and, if desired, (c) for the preparation of a compound of formula (I) wherein R3 is not H, a compound of formula (I), prepared according to variants (a) and (b), wherein R3 is hydrogen is reacted with a compound of formula G-(C=Y) n-W-Rg (V), which is known or can be prepared according to methods known per se and wherein Y, n, Rg and W are as defined for formula (I) and G is a leaving group; or (d) for the preparation of a compound of formula (I) wherein R2 is not hydrogen, a compound of formula (IV) in which R2 is hydrogen and which can be prepared, for example, according to process variant (a), is reacted with a nucleophile ; or (e) for the preparation of a compound of formula (I) wherein Ri is an unsubstituted or substituted biphenyl group, a compound of formula which can be prepared, for example, according to process variants (a) to (c) and wherein Xi, X2, X3, A, Ri, R, R2, R3a and R3b are as defined for formula (i) and Ra is, for example, halogen or -O-SO2CF3, is reacted, optionally in the presence of a catalyst, with a compound offormula phenyl-B (OH) 2 (VI), wherein the phenyl radical is unsubstituted or substituted, which is known or can be prepared according to methods known per se, and, if necessary, reacted further according to process variant (c); and in each case, if desired, a compound of formula (I) or a tautomer thereof, obtainable according to the process or in some other manner, in each case in free form or in salt form, is converted into a different compound of formula (I) or a tautomer thereof, a mixture of isomers obtainable according to the process is separated and the desired isomer isolated and/or a free compound of formula (I) or a tautomer thereof, obtainable according to the process, is converted into a salt, or a salt of a compound of formula (I) or of a tautomer thereof, obtainable according to the process, is converted into the free compound of formula (I) or a tautomer thereof or into a different salt.

The comments made above in respect of tautomers and salts of compounds of formula (I) apply analogously to the starting materials listed hereinbefore and hereinafter in respect of their tautomers and salts.

The reactions described hereinbefore and hereinafter are carried out in a manner known per se, e. g. in the absence or, customarily, in the presence of a suitable solvent or diluent or of a mixture thereof, the reaction being carried out, as required, with cooling, at room temperature or with heating, e. g. in a temperature range of from about-80°C to the boiling temperature of the reaction medium, preferably from about 0°C to about +150°C, and, if necessary, in a sealed container, under pressure, in an inert gas atmosphere and/or under anhydrous conditions. Especially advantageous reaction conditions can be found in the Examples.

The reaction time is not critical; preference is given to a reaction time of from about 0.1 to about 24 hours, especially from about 0.5 to about 10 hours.

The product is isolated according to customary methods, e. g. by filtration, crystallisation, distillation or chromatography or any suitable combination of those procedures.

The starting materials listed hereinbefore and hereinafter used in the preparation of compounds of formula (I) and, where appropriate, tautomers thereof, in each case in free form or in salt form, are known or can be prepared according to methods known per se, for example according to the information given below.

Process variant (a) : Examples of solvents or diluents that may be mentioned include : aromatic, aliphatic and alicyclic hydrocarbons and halogenated hydrocarbons, such as benzene, toluene, xylene, mesitylene, Tetralin, chlorobenzene, dichlorobenzene, bromobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, trichloromethane, tetrachloromethane, dichloroethane, trichloroethene and tetrachloroethene ; ethers, such as diethyl ether, dipropyl ether, diisopropyl ether, dibutyl ether, ter-butyl methyl ether, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol dimethyl ether, dimethoxydiethyl ether, tetrahydrofuran and dioxane; ketones, such as acetone, methyl ethyl ketone and methyl isobutyl ketone; alcohols, such as methanol, ethanol, propanol, isopropanol, butanol, ethylene glycol and glycerol ; amides, such as N, N-dimethylformamide, N, N- diethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone and hexamethylphosphoric acid triamide; nitriles, such as acetonitrile and propionitrile ; and sulfoxides, such as dimethyl sulfoxide.

Alcohols, such as methanol, ethanol and isopropanol, and amides, such as dimethylformamide and dimethylacetamide, are especially suitable.

The reactions are carried out advantageously in a temperature range of from about room temperature to the boiling point of the solvent used, preferably from room temperature to about +150°C.

In a preferred embodiment of variant (a), the reaction is carried out at from 25°C to 100°C, in an alcohol, preferably at from 80°C to 100°C, in n-propanol.

Especially preferred conditions for the reaction are described in Example P1.

Variant (b): The reactants can be reacted with one another as such, that is to say without the addition of a solvent or diluent, e. g. in the molten state. It is generally advantageous, however, to add an inert solvent or diluent or a mixture thereof. Examples of such solvents or diluents that may be mentioned include: aromatic, aliphatic and alicyclic hydrocarbons and halogenated hydrocarbons, such as benzene, toluene, xylene, mesitylene, Tetralin, chlorobenzene, dichlorobenzene, bromobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, trichloromethane, tetrachloromethane, dichloroethane, trichloroethene and tetrachloro- ethene; ethers, such as diethyl ether, dipropyl ether, diisopropyl ether, dibutyl ether, ter-butyl methyl ether, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol dimethyl ether, dimethoxydiethyl ether, tetrahydrofuran and dioxane; and sulfoxides, such as dimethyl sulfoxide.

Preference is given to a reaction time of from about 1 hour to about 24 hours, especially from about 12 to about 24 hours.

Preferred hydrogenation catalysts are, for example, Raney nickel or palladium on carbon.

In another preferred embodiment, a compound of formula (IV) is reacted with a complex hydride, such as, for example, sodium borohydride, at approximately 30°C in an ether, such as tetrahydrofuran.

Process variant (c): As solvents or diluents there come into consideration the same solvents and diluents as those mentioned under process variant (a). Preference is given to ethers, for example dimethoxyethane, dioxane and tetrahydrofuran, especially tetrahydrofuran.

The reaction is advantageously carried out in a temperature range of from about 0°C to about 1 00°C, preferably at from 50 to 80°C.

Preferably a base is added. Especially suitable bases are amines, such as trialkylamines, especially triethylamine, alcoholates, such as sodium methanolate, sodium ethanolat and potassium tert-butanolate, salts of amines, such as lithium diethylamide and lithium diisopropylamide, and hydrides, such as sodium hydride.

Advantageous leaving groups G in the compounds of formula (V) are, for example, hydroxy, Cy-Csalkoxy, halo-Ci-C8alkoxy, Ci-Cgalkanoyloxy, mercapto, C1-C8alkylthio, halo-Ci-C8alkyl- thio, Ci-Ceatkanesutfonyioxy, halo-C1-C8alkanesulfonyloxy, benzenesulfonyloxy, toluene- sulfonyloxy and halogen, preferably toluenesulfonyloxy, trifluoromethanesulfonyloxy and halogen, especially halogen.

Process variant (d): As solvents there are advantageously used alkane, such as hexane, or cyclohexane ; ethers, such as tetrahydrofuran, dioxane, diethyl ether or dimethoxyethane; sulfoxides, such as dimethyl sulfoxide ; alcohols, such as methanol, ethanol, propanol, isopropanol or tert- butanol.

Examples of nucleophiles are, for example, organometal compounds of formula R2-M, wherein M is, for example, Mg, Li, Na, Al or Zn; M enolates, wherein M is, for example, Li, Na, K, Zn, Ti or B; enamines and anions of compounds having an acidic methylene or methyl group, such as, for example, nitroalkanes, such as nitromethane or nitroethane; nitriles, such as acetonitrile ; diketones, such as acetylacetone or trifluoroacetylacetone ; beta-keto esters, such as acetoacetic ester; malonic acid or malonic acid derivatives, such as malonic dinitrile or malonic dialdehyde.

In order to prepare the anions mentioned, there are used, e. g. the same bases as those mentioned in variant (c).

The addition products are hydrolyse with water or react in situ with a compound of formula (V).

The reaction temperature is from-30 to +150 C, preferably from room temperature to the boiling point of the reaction mixture.

Process variant (e) : Examples of solvents are mentioned under variant (a).

The reaction is advantageously carried out in a temperature range of from about room temperature to about 0°C to +1 50°C, especially from 20°C to +100°C, in an ether and in the presence of a palladium catalyst.

In a preferred embodiment, a compound of formula (la) is reacted with a compound of formula (VI) at from 40 to 90°C, especially at 60°C, in dimethoxyethane, in the presence of a palladium catalyst, for example Pd (PPh3) 2CI2, and in the presence of aqueous NaHCO3.

Salts of compounds of formula (I) can be prepared in a manner known per se. For example, acid addition salts of compounds of formula (I) are obtained by treatment with a suitable acid or a suitable ion-exchange reagent, and salts with bases are obtained by treatment with a suitable base or a suitable ion-exchange reagent.

Salts of compounds of formula (I) can be converted into the free compounds of formula (I) in customary manner: acid addition salts, for example, by treatment with a suitable basic agent or a suitable ion-exchange reagent, and salts with bases, for example, by treatment with a suitable acid or a suitable ion-exchange reagent.

Salts of compounds of formula (I) can be converted into different salts of compounds of formula (I) in a manner known per se : acid addition salts, for example, can be converted into different acid addition salts, e. g. by treatment of a salt of an inorganic acid, such as a hydro- chloride, with a suitable metal salt, such as a sodium, barium or silver salt, of an acid, for example with silver acetate, in a suitable solvent in which an inorganic salt being formed, e. g. silver chloride, is insoluble and therefore separates out from the reaction mixture.

Depending upon the procedure and the reaction conditions, the compounds of formula (I) having salt-forming properties can be obtained in free form or in the form of salts.

The compounds of formula (I) may be in the form of one of the possible isomers or in the form of a mixture thereof, in the form of pure isomers or in the form of mixtures of isomers, that is to say in the form of a racemic mixture; the invention relates both to the pure isomers and to the racemic mixtures, and this is to be understood hereinbefore and hereinafter, even if stereochemical details are not specifically mentioned in each case.

The racemates can be separated into the optical antipodes according to known methods, for example by recrystallisation from an optically active solvent, by chromatography on chiral adsorbents, e. g. high-pressure liquid chromatography (HPLC) on acetyl cellulose, with the aid of suitable microorganisms, by cleavage with specific immobilised enzymes, via the formation of inclusion compounds, e. g. using chiral crown ethers, in which case only one isomer is complexe.

Apart from by the separation of corresponding mixtures of isomers, it is possible according to the invention to obtain pure optical isomers also by generally known methods of enantio- selective synthesis, for example by carrying out the process according to the invention with starting materials having correspondingly suitable stereochemistry.

It is advantageous to isolate or synthesise the biologically more active isomer, insofar as the individual components have different biological activity.

The compounds of formula (I) can also be obtained in the form of their hydrates and/or may include other solvents, for example solvents which may have been used for the crystal- isation of compounds in solid form.

The invention relates to all those forms of the process according to which a compound obtainable as starting material or intermediate at any stage of the process is used as starting material and all or some of the remaining steps are carried out, or a starting material is used in the form of a derivative or a salt and/or its racemates or antipodes or, especially, is formed under the reaction conditions.

In the processes of the present invention there are preferably used those starting materials and intermediates that result in the compounds of formula (I) that are especially preferred.

The invention relates especially to the preparation processes described in Examples P1 to P8.

In the area of pest control, the compounds of formula (I) according to the invention are valuable preventive and/or curative active ingredients having a very advantageous very broad biocidal spectrum even at low rates of concentration, while being well tolerated by warm-blooded animals, fish and plants. They are surprisingly equally suitable for controlling plant pests as for controlling ecto-and endo-parasites in humans and especially in productive livestock, domestic animals and pets. They are effective against all or individual development stages of normally sensitive animal pests, but also of resistant animal pests, such as insects and representatives of the order Acarina, nematodes, cestodes and trematodes, whilst simultaneosuly sparing useful organisms. The insecticidal or acaricidal action of the compounds according to the invention may manifest itself directly, i. e. in the death of the pests, which occurs immediately or only after some time, for example during moulting, or indirectly, for example in reduced oviposition and/or hatching rate, good activity corresponding to a mortality of at least 50 to 60 %.

The action of the compounds according to the invention and of compositions comprising them against animal pests can be substantially broadened and adapted to prevailing circumstances by the addition of other insecticides and/or acaricides. As additives there come into consideration, for example, representatives of the following classes of compound: organophosphorus compounds, nitrophenols and derivatives, formamidines, ureas, especially benzoylureas, nitroguanidines, carbamates, pyrethroids, chlorinated hydrocarbons, and Bacillus thuringiensis preparations.

Examples of especially suitable mixing partners include : azamethiphos; chlorfenvinphos ; cypermethrin, cypermethrin high-cis; cyromazine; diafenthiuron; diazinon; dichlorvos ; dicrotophos; dicyclanil ; fenoxycarb; fluazuron ; furathiocarb; isazofos; iodofenphos; kinoprene; lufenuron ; methacrifos; methidathion; monocrotophos; phosphamidon; profe- nofos; diofenolan ; a substance obtainable from Bacillus thuringiensis strain GC91 or from NCTC11821 ; pymetrozine; bromopropylate ; methoprene; disulfoton ; quinalphos ; tau-fluva- linate ; thiocyclam ; thiometon; aldicarb ; azinphos-methyl ; benfuracarb; bifenthrin; buprofezin; carbofuran; dibutylaminothio ; cartap; chlorfluazuron ; chlorpyrifos ; cyfluthrin ; lambda-cy- halothrin ; alpha-cypermethrin ; zeta-cypermethrin; deltamethrin ; diflubenzuron ; endosulfan ; ethiofencarb; fenitrothion; fenobucarb; fenvalerate ; formothion; methiocarb; heptenophos; imidacloprid ; isoprocarb; methamidophos; methomyl ; mevinphos; parathion; parathion- methyl ; phosalone ; pirimicarb; propoxur; teflubenzuron ; terbufos; triazamate; abamectin; fenobucarb; tebufenozide; fipronil ; beta-cyfluthrin ; silafluofen ; fenpyroximate; pyridaben; fenazaquin; pyriproxyfen; pyrimidifen; nitenpyram; NI-25, acetamiprid; avermectin B (abamectin); an insect-active extract from a plant ; a preparation comprising insect-active nematodes; a preparation obtainable from Bacillus subtilis ; a preparation comprising insect- active fungi; a preparation comprising insect-active viruses; AC 303 630; acephate; acrinathrin; alanycarb ; alphamethrin ; amitraz; AZ 60541; azinphos A; azinphos M; azocyclotin ; bendiocarb; bensultap ; beta-cyfluthrin ; BPMC; brofenprox; bromophos A; bufencarb; butocarboxim; butylpyridaben ; cadusafos; carbaryl ; carbophenothion; chloethocarb ; chlorethoxyfos ; chlormephos ; cis-resmethrin; clocythrin ; clofentezine ; cyanophos; cycloprothrin ; cyhexatin; demeton M; demeton S; demeton-S-methyl ; dichlofenthion ; dicliphos ; diethion; dimethoate; dimethylvinphos ; dioxathion; edifenphos; emamectin ; esfenvalerate ; ethion; ethofenprox; ethoprophos; etrimfos; fenamiphos; fenbutatin oxide; fenothiocarb; fenpropathrin; fenpyrad; fenthion; fluazinam ; flucycloxuron ; flucythrinate ; flufenoxuron ; flufenprox ; fonofos; fosthiazate ; fubfenprox; HCH; hexaflumuron ; hexythiazox; iprobenfos; isofenphos; isoxathion; ivermectin; lambda-cyhalothrin ; malathion ; mecarbam; mesulfenfos ; metaldehyde ; metolcarb ; milbemectin ; moxidectin; naled ; NC 184; omethoate; oxamyl ; oxydemeton M; oxydeprofos; permethrin; phenthoate; phorate; phosmet; phoxim; pirimiphos M; pirimiphos A; promecarb; propaphos; prothiofos; prothoate; pyrachlofos ; pyrada-phenthion; pyresmethrin ; pyrethrum; RH 5992; salithion ; sebufos; sulfotep ; sulprofos ; tebufenpyrad; tebupirimfos; tefluthrin ; temephos; terbam; tetrachlorvinphos ; thiacloprid ; thiamethoxam; thiafenox; thiodicarb; thiofanox; thionazin; thuringiensin; tralomethrin ; triarathen; triazophos; triazuron; trichlorfon ; triflumuron ; trimethacarb; vamidothion; xylylcarb ; Yl 5301/5302 ; zetamethrin; DPX-MP062; RH-2485; D 2341 or XMC (3,5,-xylyl methyl carbamate).

The mentioned animal pests include, for example, representatives of the classes Insecta, Arachnida, Nematoda and Gastropoda.

Amongst the class insecta, they are preferably representatives of the order Lepidoptera, for example Acleris spp., Adoxophyes spp., Aegeria spp., Agrotis spp., Alabama argillaceae, Amylois spp., Anticarsia gemmatalis, Archips spp., Argyrotaenia spp., Astylus atromaculatus, Auto- grapha spp., Busseola fusca, Cadra cautella, Carposina nipponensis, Chilo spp., Choristoneura spp., Clysia ambiguella, Cnaphalocrocis spp., Cnephasia spp., Cochylis spp., Coleophora spp., Crocidolomia binotalis, Cryptophlebia leucotreta, Cydia spp., Diatraea spp., Diparopsis castanea, Earias spp., Ephestia spp., Eucosma spp., Eupoecilia ambiguella, Euproctis spp., Euxoa spp., Grapholita spp., Hedya nubiferana, Heliothis spp., Hellula undalis, Heteronychus arator, Hyphantria cunea, Keiferia lycopersicella, Leucoptera scitella, Lithocollethis spp., Lobesia botrana, Lymantria spp., Lyonetia spp., Malacosoma spp., Mamestra brassicae, Manduca sexta, Operophtera spp., Ostrinia nubilalis, Pammene spp., Pandemis spp., Panolis flammea, Pectinophora gossypiella, Phthorimaea operculella, Pieris rapae, Pieris spp., Plutella xylostella, Prays spp., Scirpophaga spp., Sesamia spp., Sparganothis spp., Spodoptera spp., Synanthedon spp., Thaumetopoea spp., Tortrix spp., Trichoplusia ni and Yponomeuta spp.; of the order Coleoptera, for example Agriotes spp., Anthonomus spp., Atomaria linearis, Chaetocnema tibialis, Cosmopolites spp., Curculio spp., Dermestes spp., Diabrotica spp., Epilachna spp., Eremnus spp., Leptinotarsa decemlineata, Lissorhoptrus spp., Melolontha spp., Orycaephilus spp., Otiorhynchus spp., Phlyctinus spp., Popillia spp., Psylliodes spp., Rhizopertha spp., Scarabeidae, Sitophilus spp., Sitotroga spp., Tenebrio spp., Tribolium spp. and Trogoderma spp.; of the order Orthoptera, for example Blatta spp., Blattella spp., Gryllotalpa spp., Leucophaea maderae, Locusta spp., Periplaneta spp. and Schistocerca spp.; of the order Psocoptera, for example Liposcelis spp.; of the order Anoplura, for example Haematopinus spp., Linognathus spp., Pediculus spp., Pemphigus spp. und Phylloxera spp.; of the order Mallophaga, for example Damalinea spp. and Trichodectes spp.; of the order Thysanoptera, for example Frankliniella spp., Hercinothrips spp., Taeniothrips spp., Thrips palmi, Thrips tabaci and Scirtothrips aurantii ; of the order Heteroptera, for example Cimex spp., Distantiella theobroma, Dysdercus spp., Euchistus spp. Eurygaster spp. Leptocorisa spp., Nezara spp., Piesma spp., Rhodnius spp., Sahlbergella singularis, Scotinophara spp. and Triatoma spp.; of the order Homoptera, for example Aleurothrixus floccosus, Aleyrodes brassicae, Aonidiella spp., Aphididae, Aphis spp., Aspidiotus spp., Bemisia tabaci, Ceroplaster spp., Chrysomphalus aonidium, Chrysomphalus dictyospermi, Coccus hesperidum, Empoasca spp., Eriosoma larigerum, Erythroneura spp., Gascardia spp., Laodelphax spp., Lecanium corni, Lepidosaphes spp., Macrosiphus spp., Myzus spp., Nephotettix spp., Nilaparvata spp., Paratoria spp., Pemphigus spp., Planococcus spp., Pseudaulacaspis spp., Pseudococcus spp., Psylla spp., Pulvinaria aethiopica, Quadraspidiotus spp., Rhopalosiphum spp., Saissetia spp., Scaphoideus spp., Schizaphis spp., Sitobion spp., Trialeurodes vaporariorum, Trioza erytreae and Unaspis citri; of the order Hymenoptera, for example Acromyrmex, Atta spp., Cephus spp., Diprion spp., Diprionidae, Gilpinia polytoma, Hoplocampa spp., Lasius spp., Monomorium pharaonis, Neodiprion spp., Solenopsis spp. and Vespa spp.; of the order Diptera, for example Aedes spp., Antherigona soccata, Bibio hortulanus, Calliphora erythrocephala, Ceratitis spp., Chrysomyia spp., Culex spp., Cuterebra spp., Dacus spp., Drosophila melanogaster, Fannia spp., Gastrophilus spp., Glossina spp., Hypoderma spp., Hyppobosca spp., Liriomyza spp., Lucilia spp., Melanagromyza spp., Musca spp., Oestrus spp., Orseolia spp., Oscinella frit, Pegomyia hyoscyami, Phorbia spp., Rhagoletis pomonella, Sciara spp., Stomoxys spp., Tabanus spp., Tannia spp. and Tipula spp.; of the order Siphonaptera, for example Ceratophyllus spp. and Xenopsylla cheopis; of the order Thysanura, for example Lepisma saccharina; or of the order Isoptera (termites), in particular, the families Hodotermitidae, Kalotermitidae, Rhinotermitidae and Termitidae. Representatives of the order Isoptera which can be controlled with the compounds of the instant tinvention are especially Ailondothermes ssp., e. g. A. giffardi and A. tenax;; Ancistrotermes ssp:, e. g. A. cavithorax, A. guineensis, A. latinotus and A. periphrasis; Amitermes ssp., e. g. A. evuncifer; Heterotermes ssp., e. g. H. indicola uhd H. tenuis; Hodotermes ssp., e. g. H. mossambicus; Macrotermes ssp., e. g. M. michaelseni, M. falcifager, M. bellicosus, M. subhyalinus and M. natalensis ; Microtermes ssp., e. g. M. albopartitus, M. redenianus, M. lepidus, M-. traghardi and M. thoracalis ; Nasutitermes ssp., e. g. N. costalis ; Neotermes ssp., e. g. N. gestroi; Odontotermes ssp., e. g.

O. bruneus, O. classics, O. smeathmani, O. lathericius and 0. badius; Pseudacantho- termes ssp., e. g. P. militaris and P. spiniger; Reticulitermes ssp., e. g. R. flavides, R. santonensis and R. hesperus; Termes ssp., e. g. T. fatalis ; Trinervitermes ssp., e. g. T. trinervius; ganz besonders Odonthotermes smeathmani, Trinervitermes trinervius and Amitermes evuncifer.

Other pests which damage wood by feeding on wood, using it as a substrate or reproducing on wood, an which can also be controlled with the instantly claimed compounds are to be understood as meaning, for example, wood-boring insects such as representatives of the family Lyctidae, the family Apidae, for example Xylocopa virginica, and of the family Anobiidae, such as Anobium punctatum.

Amongst the class Arachnida, the said pests are preferably representatives of the order Acarina, for example Acarus siro, Aceria sheldoni, Aculus schlechtendali, Amblyomma spp., Argas spp., Boophilus spp., Brevipalpus spp., Bryobia praetiosa, Calipitrimerus spp., Chorioptes spp., Dermanyssus gallinae, Eotetranychus carpini, Eriophyes spp., Hyalomma spp., Ixodes spp., Olygonychus pratensis, Ornithodoros spp., Panonychus spp., Phyllocoptruta oleivora, Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Tarsonemus spp. and Tetranychus spp..

A further preferred subject according to the invention is the control of representatives of the class Nematoda, such as root knot nematodes, stem eelworms and foliar nematodes; especially Heterodera spp., for example Heterodera schachtii, Heterodora avenae and Heterodora trifolii ; Globodera spp., for example Globodera rostochiensis; Meloidogyne spp., for example Meloidogyne incognita and Meloidogyne javanica; Radopholus spp., for example Radopholus similis ; Pratylenchus, for example Pratylenchus neglectans and Pratylenchus penetrans; Tylenchulus, for example Tylenchulus semipenetrans; Longidorus, Trichodorus, Xiphinema, Ditylenchus, Aphelenchoides and Anguina, in particular Meloidogyne, for example Meloidogyne incognita, and Heterodera, for example Heterodera glycines.

A further preferred subject according to the invention is the control of representatives of the class of the Gastropoda. These molluscs include, for example, Ampullariidae ; Arion (A. ater, A. circumscriptus, A. hortensis, A. rufus); Bradybaenidae (Bradybaena fruticum); Cepaea (C. hortensis, C. nemoralis) ; Cochlodina ; Deroceras (D. agrestis, D. empiricorum, D. laeve, D. reticulatum) ; Discus (D. rotundatus); Euomphalia ; Galba (G. trunculata) ; Helicella (H. itala, H. obvia); Helicidae (Helicigona arbustorum); Helicodiscus ; Helix (H. aperta); Limax (L. cinereoniger, L. flavus, L. marginatus, L. maximus, L. tenellus) ; Lymnaea; Milax (M. gagates, M. marginatus, M. sowerbyi); Opeas; Pomacea (P. canaticulata) ; Vallonia and Zanitoides.

The present invention places special emphasis on the use of the compounds of formula (I) according to the invention in the protection of plants against parasitic feeding pests.

With the compounds according to the invention it is possible to control, i. e. to inhibit or destroy, pests of the mentioned type occurring on plants, especially on useful plants, including transgenically altered plants, and ornamentals in agriculture, in horticulture and in forestry, or on parts of such plants, such as the fruit, blossom, leaves, stems, tubers or roots, while in some cases the parts of the plants which grow later are still protected against those pests.

Target crops are especially cereals, such as wheat, barley, rye, oats, rice, maize and sorghum; beet, such as sugar beet and fodder beet; fruit, such as pomes, stone fruit and soft fruit, such as apples, pears, plums, peaches, almonds, cherries, or berries, for example strawberries, raspberries or blackberries ; leguminous plants, such as beans, lentils, peas and soybeans; oil plants, such as rape, mustard, poppy, olives, sunflowers, coconut, castor oil plants, cocoa beans and groundnuts; cucurbitaceae, such as marrows, cucumbers and melons ; fibre plants, such as cotton, flax, hemp and jute; citrus fruit, such as oranges, lemons, grapefruit and mandarins; vegetables, such as spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes and paprika; lauraceae, such as avocados, cinnamon and camphor; and tobacco, nuts, coffee, aubergines, sugar cane, tea, pepper, vines, hops, bananas and natural rubber plants, as well as ornamentals.

Further areas of use of the compounds according to the invention are the protection of stored goods and storerooms and the protection of raw materials, and also in the hygiene sector, especially the protection of domestic animals and productive livestock against pests of the mentioned type, especially against the infestation of domestic animals, especially cats and dogs, with fleas, ticks and nematodes.

The invention accordingly relates also to pesticides, such as emulsifiable concentrates, suspension concentrates, directly sprayable or dilutable solutions, spreadable pastes, dilute emulsions, wettable powders, soluble powders, dispersible powders, wettable powders, dusts, granules or encapsulations in polymer substances, comprising-at least-one of the compounds of the invention, the type of formulation being chosen in accordance with the intended objectives and prevailing circumstances.

The active ingredient is used in those compositions in pure form, a solid active ingredient, for example, in a specific particle size, or preferably together with-at least-one of the adjuvants customary in formulation technology, such as extenders, for example solvents or solid carriers, or surface-active compounds (surfactants). It will be understood that in the area of parasite control in humans, domestic animals, productive livestock and pets only physiologically tolerable additives are used.

As formulation adjuvants there are used, for example, solid carriers, solvents, stabilisers, "slow release"adjuvants, colorants and, where appropriate, surface-active substances (surfactants). As carriers and adjuvants there come into consideration all the substances customarily used, such as solvents, solid carriers, surface-active compounds, nonionic surfactants, cationic surfactants, anionic surfactants and further adjuvants known in the art.

Examples of solvents which are suitable are: unhydrogenated or partially hydrogenated aromatic hydrocarbons, preferably the fractions C8 to C12 of alkylbenzenes, such as xylene mixtures, alkylated naphthaiene or tetrahydronaphthalene, aliphatic or cycloaliphatic hydrocarbons, such as paraffins or cyclohexane, alcohols, such as ethanol, propanol or butanol, glycols and their ethers and esters, such as propylene glycol, dipropylene glycol ether, ethylene glycol, ethylene glycol monomethyl ether or ethylene glycol monoethyl ether, ketones, such as cyclohexanone, isophorone or diacetone alcohol, strongly polar solvents, such as N-methylpyrrolid-2-one, dimethyl sulfoxide or N, N-dimethylformamide, water, unepoxidized or epoxidized vegetable oils, such as unepoxidized or epoxidized rapeseed, castor, coconut or soya oil, and silicone oils.

Solid carriers which are used for example for dusts and dispersable powders are, as a rule, ground natural minerals, such as calcite, talc, kaolin, montmorillonite or attapulgite. Highly- disperse silicas or highly-disperse absorptive polymers may also be used to improve the physical properties. Suitable particulate, adsorptive carriers for granules are porous types, such as pumice, brick grit, sepiolit or bentonite, and suitable non-absorptive carrier materials are calcite or sand. Moreover, a large number of granulated materials of inorganic or organic nature, in particular dolomite or comminuted plant residues, may be used.

Suitable surface-active compounds are, depending on the nature of the active ingredient to be formulated, non-ionic, cationic and/or anionic surfactants or surfactant mixtures have good emulsifying, dispersing and wetting properties. The surfactants listed below are only given by way of example; a large number of other surfactants conventionally used in the art of formulation and suitable according to the invention are described in the relevant literature.

Suitable non-ionic surfactants are mainly polyglycol ether derivatives of aliphatic or cyclo- liphatic alcohols, saturated or unsaturated fatty acids and alkylphenols, which can have 3 to 30 glycol ether groups and 8 to 20 carbon atoms in the (aliphatic) hydrocarbon radical and 6 to 18 carbon atoms in the alkyl radical of the alkylphenols. Also suitable are water-soluble polyethylene oxide adducts with polypropylene glycol, ethylene diaminoolypropylene glycol and alkyl polypropylene glycol having 1 to 10 carbon atoms in the alkyl chain and comprising 20 to 250 ethylene glycol ether groups and 10 to 100 propylene glycol ether groups. The abovementioned compounds conventionally have 1 to 5 ethylene glycol units per propylene glycol unit. Examples which may be mentioned are nonylphenol polyethoxyethanols, castor oil polyglycol ether, polypropylene/polyethylene oxide adducts, tributylphenoxypolyethoxy- ethanol, polyethylene glycol and octylphenoxypolyethoxyethanol. Also suitable are fatty acid esters or polyoxyethylene sorbitan, such as polyoxyethylene sorbitan trioleate.

The cationic surfactants are mainly quaternary ammonium salts which have, as substituents, at least one alkyl radical having 8 to 22 carbon atoms and as further substituents lower, halogenated or unhalogenated alkyl, benzyl or lower hydroxyalkyl radicals. The salts are preferably in the form of halides, methylsulfates or ethylsulfates. Examples are stearyl-- trimethyl-ammonium chloride and benzyl di- (2-chloroethyl) ethylammonium bromide.

Suitable anionic surfactants can be water-soluble soaps and also water-soluble synthetic surface-active compounds. Soaps which are suitable are the alkali metal salts, alkaline earth metal salts and substituted or unsubstituted ammonium salts of higher fatty acids (CtO-C22), such as the sodium or potassium salts of oleic or stearic acid, or of natural fatty acid mixtures which can be obtained, for example, from coconut or tall oil ; fatty acid methyl- taurinates should furthermore be mentioned. However, so-called synthetic surfactants are used more frequently, in particular fatty sulfonates, fatty sulfates, sulfonated benzimidazole derivatives or alkylaryfsulfonates. The fatty sulfonate and fatty sulfates are, as a rule, in the form of alkali metal salts, alkaline earth metal salts or substituted or unsubstituted ammonium salts and have, as a rule, an alkyl radical of 8 to 22 carbon atoms, alkyl also including the alkyl moiety of acyl radicals, for example the sodium salt or calcium salt of lignosulfonic acid, of the dodecylsulfuric ester or of a fatty alcohol sulfate mixture prepared from natural fatty acids. This group also includes the salts of the sulfuric esters and sulfonic acids of fatty alcohol/ethylene oxide adducts. The sulfonate benzimidazole derivatives comprise preferably 2 sulfonyl groups and a fatty acid radical having approximately 8-22 carbon atoms. Alkylarylsulfonates are, for example, the sodium salts, calcium salts or triethanolammonium salts of dodecylbenzenesulfonic acid or of a naphthalenesulfonic acid/formaldehyde condensate. Suitable phosphates, for example salts of the phosphoric ester of a p-nonylphenol/ (4-14)-ethylene oxide adduct, or phospholipids, are also suitable.

The compositions for use in crop protection and in humans, domestic animals, productive livestock and pets generally contain from 0.1 to 99 %, especially from 0.1 to 95 %, of active ingredient and from 1 to 99.9 %, especially from 5 to 99.9 %, of-at least-one solid or liquid adjuvant, it generally being possible for the compositions to contain from 0 to 25 %, espe- cially from 0.1 to 20 %, surfactants (in each case percentages are by weight). Whereas commercial products will preferably be formulated as concentrates, the end user will normally employ dilute formulations which have considerably lower active ingredient concentrations.

Preferred crop protection compositions have especially the following composition (throughout, percentages are by weight): Emulsifiable concentrates: active ingredient: from 1 to 90 %, preferably from 5 to 20 % surfactant: from 1 to 30 %, preferably from 10 to 20 % solvent : from 5 to 98 %, preferably from 70 to 85 % Dusts: active ingredient: from 0.1 to 10 %, preferably from 0.1 to 1 % solid carrier: from 99.9 to 90 %, preferably from 99.9 to 99 % Suspension concentrates: active ingredient: from 5 to 75 %, preferably from 10 to 50 % water: from 94 to 24 %, preferably from 88 to 30 % surfactant: from 1 to 40 %, preferably from 2 to 30 % Wettable powders: active ingredient: from 0.5 to 90 %, preferably from 1 to 80 % surfactant: from 0.5 to 20 %, preferably from 1 to 15 % solid carrier: from 5 to 99 %, preferably from 15 to 98 % Granules: active ingredient: from 0.5 to 30 %, preferably from 3 to 15 % solid carrier: from 99.5 to 70 %, preferably from 97 to 85 % The compositions according to the invention may also comprise further solid or liquid adjuvants, such as stabilisers, e. g. vegetable oils or epoxidised vegetable oils (e. g. epoxidised coconut oil, rapeseed oil or soybean oil), antifoams, for example silicone oil, preservatives, viscosity regulators, binders and/or tackifiers, as well as fertilisers or other active ingredients for obtaining special effects, for example acaricides, bactericides, fungicides, nematicides, molluscicides or selective herbicides.

The crop protection compositions according to the invention are prepared in known manner, in the absence of adjuvants, for example by grinding, sieving and/or compressing a solid active ingredient or mixture of active ingredients, for example to a specific particle size, and in the presence of at least one adjuvant, for example by intimately mixing and/or grinding the active ingredient or mixture of active ingredients with the adjuvant (s). The invention relates also to those processes for the preparation of the compositions according to the invention and to the use of the compounds of formula (I) in the preparation of those compositions.

The invention relates also to the methods of application of the crop protection compositions, i. e. the methods of controlling pests of the mentioned type, such as spraying, atomising, dusting, coating, dressing, scattering and pouring, which are selected in accordance with the intended objectives and prevailing circumstances, and to the use of the compositions for controlling pests of the mentioned type. Typical rates of concentration are from 0.1 to 1000 ppm, preferably from 0.1 to 500 ppm, of active ingredient. The rates of application per hectare are generally from 1 to 2000 g of active ingredient per hectare, especially from 10 to 1000 g/ha, preferably from 20 to 600 g/ha.

A preferred method of application in the area of crop protection is application to the foliage of the plants (foliar application), the number of applications and the rate of application depend- ing on the risk of infestation by the pest in question. However, the active ingredient can also penetrate the plants through the roots (systemic action) if the locus of the plants is impre- gnated with a liquid formulation or if the active ingredient is incorporated in solid form, e. g. in granular form, into the locus of the plants, for example into the soil (soil application). In paddy rice crops, such granules may be applied in metered amounts to the flooded rice field.

The crop protection compositions according to the invention are also suitable for protecting plant propagation material, e. g. seed material, such as fruit, tubers or grains, or plant cuttings, against animal pests. The propagation material can be treated with the formulation before planting: seed, for example, can be dressed before being sown. The compounds of the invention can also be applied to grains (coating), either by impregnating the grains with a liquid formulation or by coating them with a solid formulation. The formulation can also be applied to the planting site when the propagation material is being planted, for example to the seed furrow during sowing. The invention relates also to those methods of treating plant propagation material and to the plant propagation material thus treated.

Preparation Examples Example P1 : Preparation of 6- (4-bromophenvl)-3- (2-chloro-4-fluorophenvl)-4, 5-dihydro- {1, 2, 4triazine P1a) : Preparation of 6- (4-bromophenyl)-3- (2-chloro-4-fluorophenyl)- {1, 2,4} triazine 96.8 g of the compound of formula and 149.2 g of the compound of formula are added to 1200 mi of dimethyiformamide and stirred for 16 hours at room temperature. The reaction mixture is then heated to 90°C and stirred for a further 4 hours. The reaction mixture is concentrated by evaporation, water is added to the residue and filtration is carried out. The filtration residue is stirred with 250 mi of ethyl acetate and filtered, and the filtration residue is dried in vacuo at 60°C. 6- (4-Bromophenyl)-3- (2-chloro-4-fluorophenyl)- {1, 2,4} triazine having a melting point of 186-188°C is obtained.

P1b) : 50 g of 6- (4-bromophenyi)-3- (2-chloro-4-fluorophenyl)- {1, 2,4} triazine are introduced into 1500 mi of tetrahydrofuran; 1.3 g of NaBH4 are added and then 200 ml of methanol are added dropwise. The reaction mixture is then concentrated by evaporation, water is added to the residue and filtration is carried out. The filtration residue is dissolved in a mixture of 2000 mi of ethyl acetate and 500 mi of tetrahydrofuran, the organic phase is washed out with water and concentrated by evaporation and the filtration residue is dried in vacuo at 60°C.

The title compound having a melting point of 209-211 °C is obtained.

Example P2: Preparation of 3- (2 6-difluorophenvl)-6- 4'-trifluoromethoxybiphenvl-4-yl)-5H- {1,2,41triazine Variant 1): 5 g of 3- (2, 6-difluorophenyl)-6- (4'-trifluoromethoxybiphenyl-4-yl)- {1, 2,4} triazine are mixed into 100 mi of tetrahydrofuran and 1 g of Pd/C (5 % by weight of Pd). 300 ml of hydrogen are introduced over a period of 90 minutes with stirring at room temperature. The catalyst is removed by filtration, the filtrate is concentrated by evaporation and the residue is purified with ethyl acetate: hexane (volumetric ratio 1: 1) on silica gel. The title compound having a melting point of 208-209°C is obtained.

Variant 2): 85.6 g of 3- (2, 6-difluorophenyl)-6- (4'-trifluoromethoxybiphenyl-4-yl)- {1, 2,4} triazine are introduced into 3 litres of absolute tetrahydrofuran. 4 g of sodium borohydride are then added. 300 mi of absolute methanol are added dropwise within a period of 30 minutes, the temperature of the reaction mixture rising to 31 °C. Stirring is carried out at room temperature for 90 minutes and then the reaction mixture is concentrated by evaporation. The solid residue is dissolved in ethyl acetate: tetrahydrofuran (volumetric ratio 2: 1), washed with water and with saturated aqueous NaCI solution, dried over Na2SO4 and concentrated by evaporation. The crude product is stirred cold into about 200 mi of ethyl acetate, filtered off, washed with a small amount of ethyl acetate and dried. The title product having a m. p. of 210-212°C is obtained.

Example P3: Preparation of 1- [(2, 6-difluorophenyl)- (4'-trifluoromethoxybiphenyl-4-vi)-5H- {1, 2, 4Ttriazin-2-yll-ethanone 0.14 g of pyridine is added to 0.7 g of 3- (2, 6-difluorophenyl)-6- (4'-trifluoromethoxybiphenyl-4- yl)-5H- {1, 2,4} triazine in 15 ml of toluene, and 0.13 g of acetyl chloride is added dropwise with stirring at room temperature. Stirring is carried out for 2 hours, and then a further 0.14 g of pyridine and 0.13 g of acetyl chloride are added and the mixture is stirred for a further 14 hours. 20 mi of toluene are added, the mixture is washed out several times with water, the organic phase is dried over sodium sulfate and the solvent is removed by evaporation.

The residue is purified on silica gel using ethyl acetate: hexane (volumetric ratio 1: 3). The title compound having a melting point of 153-154°C is obtained.

Example P4: Preparation of 1-[6-(4-bromophenyl)-3-(2-chloro-4-fluorophenyl)-5H-dihydro- {1, 2, 4Ttriazin-?-vll-ethanone The title compound having a melting point of 161-163°C is prepared in a manner analogous to that described in Example P3.

NMR data: (DMSO-d6) : 2.4 (s, 3H), 4.6 (b, 2H), 7.2-8.0 (m, 7H) (DMSO: 2.5) Example P5: Preparation of 1-r3- (2, 6-difluorophenvl)-6- (4'-trifluoromethoxvbiphenvl-4yl)-5H- {1,2,4}triazin-4-yl]-2-[ethyl-]hexanone 0.18 g of triethylamine is added to 0.7 g of 3- (2, 6-difluorophenyl)-6- (4'-trifluoromethoxy- biphenyl-4-yl)-5H- {1, 2,4} triazine in 15 ml of tetrahydrofuran, and 0.2 g of 2-ethylhexanoic acid chloride is added dropwise, with stirring, over a period of 2 hours at room temperature.

20 ml of toluene are added, the mixture is washed out several times with water, the organic phase is dried over sodium sulfate and the solvent is removed by evaporation. The residue is purified on silica gel using ethyl acatete: hexane (volumetric ratio 1: 3). The title compound having a melting point of 141-145°C is obtained.

Example P6: Preparation of 1-f3- (2-chloro-4-fluorophenvl)-6- 4'-trifluoromethoxybiphenvl-4- vl)-5H-f 1, 2, 4Ttriazin-2-vl1-ethanone 71 mg of bis (triphenylphosphine) palladium dichloride and 618 mg of 4-trifluoromethoxy- phenylboric acid are added to 1 g of 1- [6- (4-bromophenyl)-3- (2-chloro-4-fluorophenyl)-5H- dihydro- {1, 2,4} triazin-2-yl]-ethanone in 20 mi of dimethoxyethane, and 740 mg of sodium carbonate in 15 ml of water are added dropwise at 60°C. The mixture is stirred for one hour at 60°C and diluted with 30 mi of ethyl acetate, and the organic phase is washed out with water and concentrated by evaporation in vacuo. The residue is purified on silica gel using ethyl acetate: hexane (volumetric ratio 1: 2). The title compound having a melting point of 126-128°C is obtained.

NMR data: (DMSO-d6) : 2.6 (s, 3H), 4.8 (b, 2H), 7.4-8.3 (m, 11 H) (DMSO: 2.7) Example P7: Preparation of 3- (2 6-difluorophenyl)-5-nitromethvl-6- (4'-trifluoro- methoxvbiphenvl-4-yl)-4, 5-dihvdro-f 1, 2, 41triazine 0.923 g of finely pulverised KOH and 0.376 g of nitromethane are added to 1 g of 3- (2, 6- difluorophenyl)-6- (4'-trifluoromethoxybiphenyl-4-yl)-4, 5-dihydro- {l, 2,4} triazine in 10 mi of DMSO. Stirring is carried out for 4 hours at room temperature, 10 ml of water are added and the pH value is adjusted to 4.8 with acetic acid. The mixture is extracted with ethyl acetate, and the organic phase is washed out twice with water and the organic phase is concen- trated by evaporation. The residue is recrystallised from ethyl acetate/hexane (volumetric ratio 1: 1). The title product having a melting point of 184-185°C is obtained.

Example P8: The other compounds of formula (1) can also be prepared in a manner analogous to Examples P1 to P7.

Table A: Compounds of formula and of formula A. 1 F F H H H A. 2 F F H H 4-CI A. 3 F F H H 4-F A. 4 F F H H 4-CF3 A. 5 F F H H 4-OCF3 A. 6 F F H H 3, 5-Cl2 A. 7 F F H H 4-tert-butyl A. 8 F F H CH3 H A. 9 F F H CH3 4-CI A. 10 F F H CH3 4-F A. 11 F F H CH3 4-CF3 A. 12 F F H CH3 4-OCF3 A. 13 F F H CH3 3, 5-Cl2 A. 14 F F H CH3 4-tert-butyl No. Xi X2 X3 R2 Rb A. 15 F F H C2H5 H A. 16 F F H C2H5 4-CI A. 17 F F H C2H5 4-F A. 18 F F H C2H5 4-CF3 A. 19 F F H C2H5 4-OCF3 A. 20 F F H C2H5 3,5-CI2 A. 21 F F H C2H5 4-tert-butyl A. 22 F F H CH2NO2 H A. 23 F F H CH2NO2 4-CI A. 24 F F H CH2NO2 4-F A. 25 F F H CH2NO2 4-CF3 A. 26 F F H CH2NO2 4-OCF3 A. 27 F F H CH2NO2 3, 5-CI2 A. 28 F F H CH2NO2 4-tert-butyl A. 29 F F H CH (CH3) NO2 H A. 30 F F H CH (CH3) NO2 4-CI A. 31 F F H CH (CH3) NO2 4-F A. 32 F F H CH (CH3) NO2 4-CF3 A. 33 F F H CH (CH3) NO2 4-OCF3 A. 34 F F H CH (CH3)NO2 3, 5-Cl2 A. 35 F F H CH (CH3) NO2 4-tert-butyl A. 36 F F H CH2CN H A. 37 F F H CH2CN 4-CI A. 38 F F H CH2CN 4-F A. 39 F F H CH2CN 4-CF3 A. 40 F F H CH2CN 4-OCF3 A. 41 F F H CH2CN 3,5-CI2 A. 42 F F H CH2CN 4-tert-butyl A. 43 Cl Cl H H H A. 44 Cl ci H H 4-CI A. 45 Cl Cl H H 4-F A. 46 Cl ci H H 4-CF3 A. 47 Cl Cl H H 4-OCF3 No. X1 X2 X3 R2 Rb A. 48 Cl ci H H 3,5-CI2 A. 49 Cl ci H H 4-tert-butyl A. 50 Cl ci H CH3 H A. 51 ci Cl H CH3 4-CI A. 52 Cl Cl H CH3 4-F A. 53 Cl Cl H CH3 4-CF3 A. 54 Cl Cl H CH3 4-OCF3 A. 55 Cl Cl H CH3 3,5-CI2 A. 56 Cl Cl H CH3 4-tert-butyl A. 57 Cl Ci H C2H5 H A. 58 Cl Cl H C2H5 4-CI A. 59 Cl Cl H C2H5 4-F A. 60 Cl Cl H C2H5 4-CF3 A. 61 Cl Cl H C2H5 4-OCF3 A. 62 Cl Cl H C2H5 3,5-C12 A. 63 Cl Cl H C2H5 4-tert-butyl A. 64 Cl Cl H CH2NO2 H A. 65 Cl Cl H CH2NO2 4-CI A. 66 Cl Cl H CH2NO2 4-F A. 67 Cl Cl H CH2NO2 4-CF3 A. 68 Cl Cl H CH2NO2 4-OCF3 A. 69 Cl Cl H CH2NO2 3,5-CI2* A. 70 Cl Ci H CH2NO2 4-tert-butyl A. 71 Cl Cl H CH (CH3) NO2 H A. 72 Cl l Cl H CH (CH3) NO2 4-CI A. 73 Cl Cl H CH (CH3)NO2 4-F A. 74 Cl Cl H CH (CH3) NO2 4-CF3 A. 75 Cl Cl H CH (CH3) NO2 4-OCF3 A. 76 Cl Cl H CH (CH3) NO2 3,5-CI2 A. 77 Cl Cl H CH (CH3) NO2 4-tert-butyl A. 78 Cl Cl H CH2CN H A. 79 Cl Cl H CH2CN 4-CI A. 80 Cl Cl H CH2CN 4-F No. Xi X2 X3 R2 Rb A. 81 Cl ci H CH2CN 4-CF3 A. 82 Cl Cl H CH2CN 4-OCF3 A. 83 Cl ci H CH2CN 3, 5-Cl2 A. 84 Cl Cl H CH2CN 4-tert-butyl A. 85 F ci H H H A. 86 F ci H H 4-CI A. 87 F Ci H H 4-F A. 88 F ci H H 4-CF3 A. 89 F Ci H H 4-OCF3 A. 90 F ci H H 3,5-CI2 A. 91 F ci H H 4-tert-butyl A. 92 F Ci H CH3 H A. 93 F Cl H CH3 4-CI A. 94 F Cl H CH3 4-F A. 95 F Cl H CH3 4-CF3 A. 96 F ci H CH3 4-OCF3 A. 97 F Cl H CH3 3,5-C12 A. 98 F ci H CH3 4-tert-butyl A. 99 F ci H C2H5 H A. 100 F Cl H C2H5 4-CI A. 101 F Cl H C2H5 4-F A. 102 F Cl H C2H5 4-CF3 A. 103 F ci H C2H5 4-OCF3 A. 104 F Cl H C2H5 3,5-CI2 A. 105 F ci H C2H5 4-tert-butyl A. 106 F ci H CH2NO2 H A. 107 F Cl H CH2NO2 4-CI A. 108 F Cl H CH2NO2 4-F A. 109 F ci H CH2NO2 4-CF3 A. 110 F Cl H CH2NO2 4-OCF3 A. 111 F ci H CH2NO2 3,5-CI2 A. 112 F ci H CH2NO2 4-tert-butyl A. 113 F ci H CH (CH3) NO2 H No. X1 X2 X3 R2 Rb A. 114 F ci H CH (CH3) NO2 4-CI A. 115 F Ci H CH (CH3) NO2 4-F A. 116 F Cl H CH (CH3)NO2 4-CF3 A. 117 F ci H CH (CH3) NO2 4-OCF3 A. 118 F Ci H CH (CH3) NO2 3, 5-Cl2 A. 119 F ci H CH (CH3) NO2 4-tert-butyl A. 120 F ci H CH2CN H A. 121 F Cl H CH2CN 4-CI A. 122 F ci H CH2CN 4-F A. 123 F ci H CH2CN 4-CF3 A. 124 F ci H CH2CN 4-OCF3 A. 125 F Cl H CH2CN 3,5-CI2 A. 126 F ci H CH2CN 4-tert-butyl A. 127 Cl H F H H A. 128 Cl H F H 4-CI A. 129 Cl H F H 4-F A. 130 Cl H F H 4-CF3 A. 131 Cl H F H 4-OCF3 A. 132 Cl H F H 3, 5-Cl2 A. 133 Cl H F H 4-tert-butyl A. 134 Cl H F CH3 H A. 135 Cl H F CH3 4-CI A. 136 Cl H F CH3 4-F A. 137 Cl H F CH3 4-CF3 A. 138 Cl H F CH3 4-OCF3 A. 139 Cl H F CH3 3,5-CI2 A. 140 Cl H F CH3 4-tert-butyl A. 141 Cl H F C2H5 H A. 142 C) H F C2H5 4-Cl A. 143 Cl H F C2H5 4-F A. 144 Cl H F C2H5 4-CF3 A. 145 Cl H F C2H5 4-OCF3 A. 146 Cl H F C2H5 3, 5-Cl2 No. X1 X2 X3 R2 Rb A. 147 Cl H F C2H5 4-tert-butyl A. 148 Cl H F CH2NO2 H A. 149 Cl H F CH2NO2 4-CI A. 150 Cl H F CH2NO2 4-F A. 151 Cl H F CH2NO2 4-CF3 A. 152 Cl H F CH2NO2 4-OCF3 A. 153 Cl H F CH2NO2 3, 5-Cl2 A. 154 Cl H F CH2NO2 4-tert-butyl A. 155 Cl H F CH (CH3) NO2 H A. 156 Cl H F CH (CH3) NO2 4-CI A. 157 Cl H F CH (CH3) NO2 4-F A. 158 Cl H F CH (CH3) NO2 4-CF3 A. 159 Cl H F CH (CH3) NO2 4-OCF3 A. 160 Cl H F CH (CH3) NO2 3, 5-Cl2 A. 161 Cl H F CH (CH3) NO2 4-tert-butyl A. 162 Cl H F CH2CN H A. 163 Cl H F CH2CN 4-CI A. 164 Cl H F CH2CN 4-F A. 165 Cl H F CH2CN 4-CF3 A. 166 Cl H F CH2CN 4-OCF3 A. 167 Cl H F CH2CN 3, 5-Cl2 A. 168 Cl H F CH2CN 4-tert-butyl A. 169 F H H H H A. 170 F H H H 4-CI A. 171 F H H H 4-F A. 172 F H H H 4-CF3 A. 173 F H H H 4-OCF3 A. 174 F H H H 3,5-CI2 A. 175 F H H H 4-tert-butyl A. 176 F H H CH3 H A. 177 F H H CH3 4-CI A. 178 F H H CH3 4-F A. 179 F H H CH3 4-CF3 No. Xi X2 X3 R2 Rb A. 180 F H H CH3 4-OCF3 A. 181 F H H CH3 3, 5-Cl2 A. 182 F H H CH3 4-tert-butyl A. 183 F H H C2H5 H A. 184 F H H C2H5 4-CI A. 185 F H H C2H5 4-F A. 186 F H H C2H5 4-CF3 A. 187 F H H C2H5 4-OCF3 A. 188 F H H C2H5 3, 5-Cl2 A. 189 F H H C2H5 4-tert-butyl A. 190 F H H CH2NO2 H A. 191 F H H CH2NO2 4-CI A. 192 F H H CH2NO2 4-F A. 193 F H H CH2NO2 4-CF3 A. 194 F H H CH2NO2 4-OCF3 A. 195 F H H CH2NO2 3, 5-Cl2 A. 196 F H H CH2NO2 4-tert-butyl A. 197 F H H CH (CH3) NO2 H A. 198 F H H CH (CH3) NO2 4-CI A. 199 F H H CH (CH3) NO2 4-F A. 200 F H H CH (CH3) N02 4-CF3 A. 201 F H H CH (CH3) NO2 4-OCF3 A. 202 F H H CH (CH3) NO2 3, 5-Cl2 A. 203 F H H CH (CH3) NO2 4-tert-butyl A. 204 F H H CH2CN H A. 205 F H H CH2CN 4-CI A. 206 F H H CH2CN 4-F A. 207 F H H CH2CN 4-CF3 A. 208 F H H CH2CN 4-OCF3 A. 209 F H H CH2CN 3,5-CI2 A. 210 F H H CH2CN 4-tert-butyl A. 211 Cl H H H H A. 212 Cl H H H 4-CI No. Xi X2 X3 R2 Rb A. 213 Cl H H H 4-F A. 214 Cl H H H 4-CF3 A. 215 Cl H H H 4-OCF3 A. 216 Cl H H H 3,5-CI2 A. 217 Cl H H H 4-tert-butyl A. 218 Cl H H CH3 H A. 219 Cl H H CH3 4-CI A. 220 Cl H H CH3 4-F A. 221 Cl H H CH3 4-CF3 A. 222 Cl H H CH3 4-OCF3 A. 223 Cl H H CH3 3,5-CI2 A. 224 Cl H H CH3 4-tert-butyl A. 225 Cl H H C2H5 H A. 226 Cl H H C2H5 4-Cl A. 227 Cl H H C2H5 4-F A. 228 Cl H H C2H5 4-CF3 A. 229 Cl H H C2H5 4-OCF3 A. 230 CI H H C2H5 3, 5-Cl2 A. 231 Cl H H C2H5 4-tert-butyl A. 232 Cl H H CH2NO2 H A. 233 Cl H H CH2NO2 4-CI A. 234 Cl H H CH2NO2 4-F A. 235 Cl H H CH2NO2 4-CF3 A. 236 Cl H H CH2NO2 4-OCF3 A. 237 Cl H H CH2NO2 3, 5-Cl2 A. 238 Cl H H CH2NO2 4-tert-butyl A. 239 Cl H H CH (CH3) NO2 H A. 240 Cl H H CH (CH3) NO2 4-CI A. 241 Cl H H CH (CH3) NO2 4-F A. 242 Cl H H CH (CH3)NO2 4-CF3 A. 243 Cl H H CH (CH3) NO2 4-OCF3 A. 244 Cl H H CH (CH3) NO2 3, 5-Cl2 A. 245 Cl H H CH (CH3) NO2 4-tert-butyl No. X1 X2 X3 R2 Rb A. 246 ci H H CH2CN H A. 247 Cl H H CH2CN 4-CI A. 248 CI H H CH2CN 4-F A. 249 Cl H H CH2CN 4-CF3 A. 250 Cl H H CH2CN 4-OCF3 A. 251 Cl H H CH2CN 3,5-CI2 A. 252 Cl H H CH2CN 4-tert-butyl A. 253 CH3 H H H H A. 254 CH3 H H H 4-CI A. 255 CH3 H H H 4-F A. 256 CH3 H H H 4-CF3 A. 257 CH3 H H H 4-OCF3 A. 258 CH3 H H H 3,5-CI2 A. 259 CH3 H H H 4-tert-butyl A. 260 CH3 H H CH3 H A. 261 CH3 H H CH3 4-CI A. 262 CH3 H H CH3 4-F A. 263 CH3 H H CH3 4-CF3 A. 264 CH3 H H CH3 4-OCF3 A. 265 CH3 H H CH3 3,5-CI2 A. 266 CH3 H H CH3 4-tert-butyl A. 267 CH3 H H C2H5 H A. 268 CH3 H H C2H5 4-CI A. 269 CH3 H H C2H5 4-F A. 270 CH3 H H C2H5 4-CF3 A. 271 CH3 H H C2H5 4-OCF3 A. 272 CH3 H H C2H5 3,5-Cl2 A. 273 CH3 H H C2H5 4-tert-butyl A. 274 CH3 H H CH2NO2 H A. 275 CH3 H H CH2NO2 4-CI A. 276 CH3 H H CH2NO2 4-F A. 277 CH3 H H CH2NO2 4-CF3 A. 278 CH3 H H CH2NO2 4-OCF3 No. Xi X2 X3 R2 Rb A. 279 CH3 H H CH2NO2 3,5-Ci2 A. 280 CH3 H H CH2NO2 4-tert-butyl A. 281 CH3 H H CH (CH3) NO2 H A. 282 CH3 H H CH (CH3) NO2 4-CI A. 283 CH3 H H CH (CH3) NO2 4-F A. 284 CH3 H H CH (CH3)NO2 4-CF3 A. 285 CH3 H H CH (CH3) NO2 4-OCF3 A. 286 CH3 H H CH (CH3)NO2 3,5-CI2 A. 287 CH3 H H CH (CH3) N02 4-tert-butyl A. 288 CH3 H H CH2CN H A. 289 CH3 H H CH2CN 4-CI A. 290 CH3 H H CH2CN 4-F A. 291 CH3 H H CH2CN 4-CF3 A. 292 CH3 H H CH2CN 4-OCF3 A. 293 CH3 H H CH2CN 3,5-CI2 A. 294 CH3 H H CH2CN 4-tert-butyl A. 295 F F H CH (Et) N02 CF3 A. 296 Cl Cl H CH (Et) N02 CF3 A. 297 F ci H CH (Et) N02 CF3 A. 298 Cl H F CH (Et) NO2 CF3 A. 299 F H H CH (Et) N02 CF3 A. 300 Cl H H CH (Et) N02 CF3 A. 301 CH3 H H CH (Et) N02 CF3 A. 302 F F H CH (Et) N02 OCF3 A. 303 Cl ci H CH (Et) NO2 OCF3 A. 304 F ci H CH (Et) N02 OCF3 A. 305 Cl H F CH (Et) N02 OCF3 A. 306 F H H CH (Et) N02 OCF3 A. 307 Cl H H CH (Et) N02 OCF3 A. 308 CH3 H H CH (Et) N02 OCF3 A. 309 F F H CH (n-Prop) N02 CF3 A. 310 Cl Cl H CH (n-Prop) N02 CF3 A. 311 F ci H CH (n-Prop) NO2 CF3 No. X1 X2 X3 R2 Rb A. 312 Cl H F CH (n-Prop) NO2 CF3 A. 313 F H H CH (n-Prop) N02 CF3 A. 314 Cl H H CH (n-Prop) N02 CF3 A. 315 CH3 H H CH (n-Prop) N02 CF3 A. 316 F F H CH (n-Prop) N02 OCF3 A. 317 Cl Ci H CH (n-Prop) N02 OCF3 A. 318 F ci H CH (n-Prop) N02 OCF3 A. 319 Cl H F CH (n-Prop) N02 OCF3 A. 320 F H H CH (n-Prop) N02 OCF3 A. 321 Cl H H CH (n-Prop) N02 OCF3 A. 322 CH3 H H CH (n-Prop) NO2 OCF3 Table 1: Compounds of the general formula (lb) wherein R3 is H and the combination of the substituents X1, X2, X3, R2 and Rb for each compound corresponds to a line A. 1 to A. 322 of Table A.

Table 2: Compounds of the general formula (lb) wherein R3 is-CH3 and the combination of the substituents Xi, X2, X3, R2 and Rb for each compound corresponds to a line A. 1 to A. 322 of Table A.

Table 3: Compounds of the general formula (lb) wherein R3 is-C2H5 and the combination of the substituents Xi, X2, X3, R2 and Rb for each compound corresponds to a line A. 1 to A. 322 of Table A.

Table 4: Compounds of the general formula (lb) wherein R3 is-CH2OCH3 and the combi- nation of the substituents Xi, X2, X3, R2 and Rb for each compound corresponds to a line A. 1 to A. 322 of Table A.

Table 5: Compounds of the general formula (lb) wherein R3 is-CH2OCH2CH3 and the combi- nation of the substituents X1, X2, X3, R2 and Rb for each compound corresponds to a line A. 1 to A. 322 of Table A.

Table 6: Compounds of the general formula (lb) wherein R3 is-C (=O) CH3 and the combi- nation of the substituents Xi, X2, X3, R2 and Rb for each compound corresponds to a line A. 1 to A. 322 of Table A.

Table 7: Compounds of the general formula (lb) wherein R3 is-C (=O) C2H5 and the combi- nation of the substituents Xi, X2, X3, R2 and Rb for each compound corresponds to a line A. 1 to A. 322 of Table A.

Table 8: Compounds of the general formula (lb) wherein R3 is-C (=O) C3H7 and the combi- nation of the substituents Xi, X2, X3, R2 and Rb for each compound corresponds to a line A. 1 to A. 322 of Table A.

Table 9: Compounds of the general formula (lb) wherein R3 is-C (=O)-iso-C3H7 and the combination of the substituents Xi, X2, X3, R2 and Rb for each compound corresponds to a line A. 1 to A. 322 of Table A.

Table 10: Compounds of the general formula (lob) wherein R3 is-C (=O) CH (Et) C4H9 and the combination of the substituents Xi, X2, X3, R2 and Rb for each compound corresponds to a line A. 1 to A. 322 of Table A.

Table 11: Compounds of the general formula (lb) wherein R3 is-C (=O) OCH3 and the combi- nation of the substituents Xi, X2, X3, R2 and Rb for each compound corresponds to a line A. 1 to A. 322 of Table A.

Table 12: Compounds of the general formula (lb) wherein R3 is-C (=O) OC2H5 and the combi- nation of the substituents Xi, X2, X3, R2 and Rb for each compound corresponds to a line A. 1 to A. 322 of Table A.

Table 13: Compounds of the general formula (lb) wherein R3 is-CH2C-CH and the combi- nation of the substituents X1, X2, X3, R2 and Rb for each compound corresponds to a line A. 1 to A. 322 of Table A.

Table 14: Compounds of the general formula (lb) wherein R3 is -CH2CH=CH2 and the combi- nation of the substituents X1, X2, X3, R2 and Rb for each compound corresponds to a line A. 1 to A. 322 of Table A.

Table 15: Compounds of the general formula (lb) wherein R3 is-C (=O)-C6H4-4-CF3 and the combination of the substituents Xi, X2, X3, R2 and Rb for each compound corresponds to a line A. 1 to A. 322 of Table A.

Table 16: Compounds of the general formula (lb) wherein R3 is-CH2-C6H4-4-CF3 and the combination of the substituents Xi, X2, X3, R2 and Rb for each compound corresponds to a line A. 1 to A. 322 of Table A.

Table 17: Compounds of the general formula (lb) wherein R3 is-C (=O)-NH-CH3 and the combination of the substituents Xi, X2, X3, R2 and Rb for each compound corresponds to a line A. 1 to A. 322 of Table A.

Table 18 : Compounds of the general formula (lb) wherein R3 is-C (=O)-NH-C2H5 and the combination of the substituents X1, X2, X3, R2 and Rb for each compound corresponds to a line A. 1 to A. 322 of Table A.

Table 19 : Compounds of the general formula (lb) wherein R3 is-C (=O)-CH2CI and the combination of the substituents X1, X2, X3, R2 and Rb for each compound corresponds to a line A. 1 to A. 322 of Table A.

Table 20 : Compounds of the general formula (lb) wherein R3 is -C(=O)-CHCl2 and the combination of the substituents Xi, X2, X3, R2 and Rb for each compound corresponds to a line A. 1 to A. 322 of Table A.

Table 21: Compounds of the general formula (Ic) wherein R3 is H and the combination of the substituents X1, X2, X3, R2 and Rb for each compound corresponds to a line A. 1 to A. 322 of Table A.

Table 22: Compounds of the general formula (lc) wherein R3 is-CH3 and the combination of the substituents Xi, X2, X3, R2 and Rb for each compound corresponds to a line A. 1 to A. 322 of Table A.

Table 23: Compounds of the general formula (lc) wherein R3 is-C2H5 and the combination of the substituents Xi, X2, X3, R2 and Rb for each compound corresponds to a line A. 1 to A. 322 of Table A.

Table 24: Compounds of the general formula (lc) wherein R3 is-CH20CH3 and the combi- nation of the substituents Xi, X2, X3, R2 and Rb for each compound corresponds to a line A. 1 to A. 322 of Table A.

Table 25: Compounds of the general formula (lc) wherein R3 is-CH20CH2CH3 and the combination of the substituents Xi, X2, X3, R2 and Rb for each compound corresponds to a line A. 1 to A. 322 of Table A.

Table 26: Compounds of the general formula (lc) wherein R3 is-C (=O) CH3 and the combi- nation of the substituents Xi, X2, X3, R2 and Rb for each compound corresponds to a line A. 1 to A. 322 of Table A.

Table 27: Compounds of the general formula (Ic) wherein R3 is-C (=O) C2H5 and the combi- nation of the substituents Xi, X2, X3, R2 and Rb for each compound corresponds to a line A. 1 to A. 322 of Table A.

Table 28: Compounds of the general formula (Ic) wherein R3 is-C (=O) C3H7 and the combi- nation of the substituents Xi, X2, X3, R2 and Rb for each compound corresponds to a line A. 1 to A. 322 of Table A.

Table 29: Compounds of the general formula (lc) wherein R3 is-C (=O)-iso-C3H7 and the combination of the substituents Xi, X2, X3, R2 and Rb for each compound corresponds to a line A. 1 to A. 322 of Table A.

Table 30: Compounds of the general formula (Ic) wherein R3 is-C (=O) CH (Et) C4H9 and the combination of the substituents X1, X2, X3, R2 and Rb for each compound corresponds to a line A. 1 to A. 322 of Table A.

Table 31: Compounds of the general formula (lc) wherein R3 is-C (=O) OCH3 and the combi- nation of the substituents Xi, X2, X3, R2 and Rb for each compound corresponds to a line A. 1 to A. 322 of Table A.

Table 32: Compounds of the general formula (Ic) wherein R3 is-C (=O) OC2H5 and the combi- nation of the substituents Xi, X2, X3, R2 and Rb for each compound corresponds to a line A. 1 to A. 322 of Table A.

Table 33: Compounds of the general formula (Ic) wherein R3 is-CH2C-CH and the combi- nation of the substituents X1, X2, X3, R2 and Rb for each compound corresponds to a line A. 1 to A. 322 of Table A.

Table 34: Compounds of the general formula (lc) wherein R3 is-CH2CH=CH2 and the combi- nation of the substituents X1, X2, X3, R2 and Rb for each compound corresponds to a line A. 1 to A. 322 of Table A.

Table 35: Compounds of the general formula (Ic) wherein R3 is-C (=O)-C6H4-4-CF3 and the combination of the substituents X1, X2, X3, R2 and Rb for each compound corresponds to a line A. 1 to A. 322 of Table A.

Table 36: Compounds of the general formula (Ic) wherein R3 is-CH2-C6H4-4-CF3 and the combination of the substituents X1, X2, X3, R2 and Rb for each compound corresponds to a line A. 1 to A. 322 of Table A.

Table 37: Compounds of the general formula (lc) wherein R3 is-C (=O)-NH-CH3 and the combination of the substituents X1, X2, X3, R2 and Rb for each compound corresponds to a line A. 1 to A. 322 of Table A.

Table 38: Compounds of the general formula (Ic) wherein R3 is-C (=O)-NH-C2H5 and the combination of the substituents Xi, X2, X3, R2 and Rb for each compound corresponds to a line A. 1 to A. 322 of Table A.

Table 39: Compounds of the general formula (Ic) wherein R3 is-C (=O)-CH2CI and the combination of the substituents Xi, X2, X3, R2 and Rb for each compound corresponds to a line A. 1 to A. 322 of Table A.

Table 40: Compounds of the general formula (Ic) wherein R3 is -C(=O)-CHCl2 and the combination of the substituents XI, X2, X3, R2 and Rb for each compound corresponds to a line A. 1 to A. 322 of Table A.

Table 41 : Compounds of the general formula (lb) wherein R3 is-C (=O)-CH20CH3 and the combination of the substituents Xi, X2, X3, R2 and Rb for each compound corresponds to a line A. 1 to A. 322 of Table A.

Table 42: Compounds of the general formula (lc) wherein R3 is-C (=O)-CH20CH3 and the combination of the substituents XI, X2, X3, R2 and Rb for each compound corresponds to a line A. 1 to A. 322 of Table A.

Table B: Compounds of formula Xi X2 X3 R2 Rr m. p. (°C) B. 1 F F H H-C6H4-4-CF3 234-236 B. 2 F F H H-C6H4-4-OCF3 208-209 B. 3 Cl H F H Br 209-211 B. 4 F F H H-O-CH2-C6H5 178-180 B. 5 F F H H -O-C6H4-4-OCF3 163-165 B. 6 Cl H F H-C6H4-4-OCF3 202-204 B. 7 F H H H Br 162-164 B. 8 Cl H H H-C6H4-4-OCF3 190-191 m.p. (°C) B. 9 F F H n-butyl Br 149-150 B. 10 F F H CH2NO2 Br resin B. 11 F F H CH3-C6H4-4-OCF3 202-205 B. 12 F F H CH2NO2-C6H4-4-OCF3 184 B. 13 F F H CH (CH3) NO2-C6H4-4-OCF3 191-192 B. 14 F F H CH (CN) OC6H4-C6H4-4-OCF3 > 220 B. 15 F F H CH2CN-C6H4-4-OCF3 199-200 B. 16 Cl H H H-C6H4-4-CF3 210-217 B. 17 Cl H H H-C6H3-3, 5-Cl2 208-210 B. 18 F F H CH2NO2-C6H4-4-CF3 200-201 B. 19 Cl H F CH2NO2-C6H4-4-OCF3 204-205 B. 20 Cl H F CH (CH3) NO2-C6H4-4-OCF3 210-211, (RS/SR) B. 21 Cl H F CH (CH3) NO2-C6H4-4-OCF3 193-195, (RR/SS) B. 22 Cl H F CH (CN) C6H5-C6H4-4-OCF3 > 220 B. 23 Cl H F CH2CN-C6H4-4-OCF3 209-211 B. 24 F F H H-CF3 185-190 B. 25 F H H CH2NO2 -C6H4-4-OCF3 187-188 B. 26 F F H CH2SO2N (CH3) 2 -C6H4-4-OCF3 210-211 B. 27 F H H CH (CH3) NO2 -C6H4-4-OCF3 179-180 B. 28 F H H H-C6H4-4-OCF3 220-221 B. 29 Cl H H CH2NO2-C6H4-4-OCF3 195-196 B. 30 F F H CH (Et) N02-C6H4-4-OCF3 177-178 B. 31 F F H CH (n-Prop) N02-C6H4-4-OCF3 172-173 B. 32 Me H H CH2NO2 -C6H4-4-OCF3 185-186 B. 33 F H H CH2NO2-C6H4-4-CF3 203-204 B. 34 F H H CH (CH3) NO2 -C6H4-4-CF3 201-202 B. 35 Me H H CH (CH3) NO2-C6H4-4-CF3 183-184 B. 36 F H H H-C6H4-4-CF3 143-145 B. 37 Me H H CH2NO2 -C6H4-3-CF3 183-184 B. 38 F H H CH2NO2 -C6H4-3-CF3 174-175 B. 39 F H H CH (CH3) NO2 -C6H4-3-CF3 183-184 Xi X2 X3 R2 Rr m. p. (°C) B. 40 F H H H-C6H4-4-SF3 190-103 B. 41 F F H CH2NO2 -C6H4-4-SF3 217-218 B. 42 F F H CH (CH3) NO2 -C6H4-4-SF3 200-202 B. 43 F H H CH2NO2 -C6H4-3-Cl 181-182 B. 44 F H H CH (CH3) NO2 -C6H4-3-Cl 189-190 B. 45 F H H CH2NO2 -C6H3-3, 5-CI2 192-193 B. 46 F H H CH (CH3) NO2 -C6H3-3, 5-CI2 164-165 B. 47 F H H H-C6H3-3, 5-CI2 143-145 B. 48 Me H H CH2NO2 -C6H3-3, 5-Cl2 179-180 B. 49 F F H H-C6H3-3, 5-CI2 194-196 B. 50 Cl H H CH2N02-C6H3-2, 4-CI2 172-173 B. 51 Cl H F CH2NO2-C6H3-2, 4-C12 221-222 B. 52 F H H CH2NO2 -C6H3-2, 4-Cl2 182-183 B. 53 F H H CH (CH3) NO2-C6H3-2, 4-CI2 166-167 B. 54 F H H CH2NO2 -C6H3-3-Cl, 4-F 182-183 B. 55 F H H CH (CH3) N02-C6H3-3-CI, 4-F 187-188 B. 56 Me H H CH2N02-C6H3-3-CI, 4-F 162-163 B. 57 Me H H CH2NO2-C6H4-4-SCH3 216-217 B. 58 F H H CH2NO2-C6H4-4-SCH3 214-215 B. 59 F H H CH (CH3) N02-C6H4-4-SCH3 220-221 B. 60 F F H H-C6H4-4-N (CH3) 2 255-258 B. 61 F F H H-C6H4-4-S-n-C6Fl3 > 240 B. 62 F F H H-C6H4-4-S-n-C4F9 > 240 B. 63 F F H CH2NO2 -C6H4-4-S-n-C6F13 165-170 B. 64 F F H CH (CH3) NO2-C6H4-4-S-n-C4Fg 173-176 B. 65 Cl H H H Br 184-187 B. 66 F F H H Br 181-183 B. 67 Cl H F CH2NO2-C6H4-3-(CH=N-OCH3) 170-171 B. 68 F F H H -C#C-C6H4-4-OCH3 199-208 B. 69 F F H H -C6H4-2, 5-CI2-4-OCF2CHFCF3 164-165 B. 70 F F H CH (CH3) NO2 -C6H4-4-CF3 193-194 B. 71 F H H CH2NO2-C6H4-4-CH3 221-222 B. 72 F F H CH2NO2 -NH-C6H3-3,5-F2 194-196 XiX3 B. 73 F F H CH2NO2-NH-C6H3-2-CH3-4-CF3 182-183 B. 74 F F H H-NH-C6H3-4-CF3 204-207 B. 75 F F H H-NH-C6H4-4-OCF3 174-176 B. 76 F F H H-NH-C6H3-4-OCF2CHFCF3 197-200 B. 77 F F H H-NH-C6H3-3, 5-F2 208-211 B. 78 F F H H-NH-C6H3-2-CH3-4-CF3 207-210 B. 79 F F H CH2NO2-NH-C6H4-4-CF3 199-201 B. 80 F F H CH2N02-NH-C6H4-4-OCF3 170-172 B. 81 F H H CH2NO2-C6H4-4-CI 214-215 Table C: Compounds of formula X1 X2 X3 R3a Rr m.p. (°C) C. 1 F F H-C (=O) CH3-C6H4-4-OCF3 153-154 C. 2 Cl H F-C (=O) CH3-CgH4-4-OCF3 126-128 C. 3 F F H-C (=O) NHCH3-C6H4-4-OCF3 200-202 C. 4 F F H-C (=O) CH2CI-C6H4-4-CF3 201-203 C. 5 F F H-C (=O) CHCl2 -C6H4-4-OCF3 170-173 C. 6 F F H-C (=O) C2H5-C6H4-4-OCF3 184-185 C. 7 F F H-C (=O) OCH3-C6H4-4-OCF3 184-186 C. 8 F F H-C (=O)-n-C3H7-C6H4-4-OCF3 135-137 C. 9 F F H-C (=O)-i-C3H7-C6H4-4-OCF3 186-188 C. 10 F F H-C (=O)-C6H4-4-CF3-C6H4-4-OCF3 161-164 C. 11 F F H-C (=O) OC2H5-C6H4-4-OCF3 175-180 C. 12 F H H-C (=O) CH3-C6H4-4-OCF3 159-161 C. 13 F H H-C2H5-C6H4-4-OCF3 155-157 C. 14 F H H-CH20CH3-C6H4-4-OCF3 154-156 C. 15 Cl H H-C (=O) CH3-C6H4-4-OCF3 146-147 C. 16 H H CF3-CH20CH3-C6H4-4-OCF3 122-124 Xi X2 X3 Rsa Rr m. p. (°C) C. 17 H H CF3-C (=O) CH3-C6H4-4-OCF3 188-190 C. 18 F H H-C (=O) OCH3-C6H4-4-OCF3 153-156 C. 19 F F H-C (=O) NHC2H5-C6H4-4-OCF3 200-202 C. 20 F F H-C (=O) NHC6H4-4-CF3-C6H4-4-OCF3 175-177 C. 21 F F H-C (=O) OC3H5-C6H4-4-OCF3 190-193 C. 22 F F H-C (=O) NHC6H4-4-F-C6H4-4-OCF3 193-195 C. 23 F F H-C (=O) NHC6H4-4-CI-C6H4-4-OCF3 180-182 C. 24 F F H-C (=O) CHC12-C6H4-4-OCF3 182-184 C. 25 F F H-C (=O) CH2CI-C6H4-4-OCF3 170-173 C. 26 F F H-C (=O) CH20CH3-C6H4-4-OCF3 154-156 C. 27 F F H-C (=O) OCH3 -C6H4-2, 5-Cl2-4- oil OCF2CHFCF3 C. 28 F F H-C (=O) CCl3 -C6H4-4-OCF3 205-207 C. 29 Cl H F-C (=O) CH3-C6H4-4-CF3 199-201 C. 30 F H H-C (=O) CH3-C6H4-4-CF3 178-180 C. 31 Cl H H-C (=O) OCH3 -C6H4-4-CF3 193-197 C. 32 Cl H H-C (=O) CH3 -C6H4-4-CF3 211-213 C. 33 F F H-C (=O)-C6H4-4-CN-C6H4-4-OCF3 159-161 C. 34 F F H-C (=O)-CH3-C6H4-4-CF3 216-218 C. 35 F F H-C (=O)-OCH3-C6H4-4-CF3 199-291 C. 36 F F H-C (=O)-CHC12-C6H4-4-CF3 200-202 C. 37 F F H-C (=O)-CH2CI-C6H4-4-CF3 201-203 C. 38 F F H-C (=O)-CH20CH3-C6H4-4-CF3 210-212 C. 39 Cl H F-C (=O)-CH3 Br 161-163 C. 40 Cl H F-C (=O)-OCH3 Br 161-163 C. 41 F H H-C (=O)-CH3 Br 170-172 C. 42 F H H-CH2-CH=CH2 Br 67-69 C. 43 H H CF3-C (=O)-CH3 Br 167-169 C. 44 Cl H F Et Br 122-124 C. 45 F F H-C (=O) NHC6H4-4-CF3 Br 173-175 C. 46 F F H-C (=O) NHC6H4-3-CF3 Br 174-176 C. 47 F F H-C (=O) NHC6H4-4-Cl Br 217-219 X1 X2 X3 R3a Rr m. p. (°C) C. 48 F F H-C (=O) NHC6H4-4-F-C6H4-2, 5-CI2-4- 94-95 OCF2CHFCF3 C. 49 F F H-C (=O) CCI3-C6H4-4-CF3 199-201 C. 50 Cl H F-C (=O) CH3-C6H3-3, 5-CI2 187-190 C. 51 F H H-C (=O) CH3 -C6H3-3,5-Cl2 147-149 C. 52 Cl H H-C (=O) CH3 -C6H3-3,5-Cl2 175-176 C. 53 Cl H H-C (=O) OCH3 -C6H3-3,5-Cl2 158-161 C. 54 F H H-C (=O) OCH3 -C6H3-3,5-Cl2 179-181 C. 55 F F H-C (=O) C6H4-4-CF3 -C6H3-3,5-Cl2 188-190 C. 56 F F H-C (=O) CH3-C6H4-S-CF3 170-171 C. 57 F F H-C (=O) OCH3-C6H4-S-CF3 169-170 C. 58 F F H-C (=O) NHC6H4-4-F -C6H4-S-CF3 210-211 C. 59 F F H-C (=O) CH3-C6H3-3,5-CI2 216-218 C. 60 F F H-C (=O) CH3-C6H4-2, 5-CI2-4- 132-133 OCF2CHFCF3 Table D: Compounds of formula Xi X2 X3 R3a R11 R22 D. 1 F F H-C (=O) CH3 4-OCF3 H 69-70 D. 2 F F F-C (=O)-i-Prop 4-OCF3 H 89-90 D. 3 F F H-C (=O)-Et 4-OCF3 H 161-162 D. 4 F F H-C (=O)-O-CH3 4-OCF3 H 217-218 D. 5 F F F-C (=O)-n-Prop 4-OCF3 H 66-67 D. 6 F F H-C (=O)-O-Et 4-OCF3 H 218-219 D. 7 F F H-C (=O)-O-CH2C6H5 4-OCF3 H 188-189 D. 8 F F H-C (=O)-C6H4-4-OCF3 4-OCF3 H 182-183 D. 9 Cl H F-C (=O)-NH-C6H5 4-OCF3 H 98-100 D. 10 Cl H F-C (=O)-NHC6H4-3-CF3 4-OCF3 H 101-103 Xi X2 X3 R3a Rn R22 m. p. (°C) D. 11 Cl H F-C (=O)-NHC6H4-4-F 4-OCF3 H 153-154 D. 12 Cl H F-C (=O)-NHC6H4-4-CH3 4-OCF3 H 190-191 D. 13 F F H-C (=O) CH3 4-OCF3 CH3 106-107 D. 14 F F H-C (=O) OCH2CH3 4-OCF3 CH3 80-82 D. 15 F F H-C (=O)-NHC6H4-3-CF3 4-OCF3 CH3 175-176 Isomer A D. 16 F F H-C (=O)-NHC6H4-4-F 4-OCF3 CH3 114-115 Isomer A D. 17 F F H-C (=O) CH2CH2CH3 4-OCF3 CH3 80-81 D. 18 F F H-C (=O)-NHC6H4-2- 4-OCF3 CH3 169-170 C (=O) OEt D. 19 F F H-C (=O)-OC6H5 4-OCF3 CH3 Oil D. 20 F F H-C (=O)-OC6H4-4-CF3 4-OCF3 CH3 164-165 Isomer A D. 21 F F H-C (=O) CH3 4-SCF3 H 140-145 D. 22 F F H-C (=O) OCH3 4-SCF3 H 208-209 D. 23 F F H-C (=O) CH3 4-SCF3 CH3 140-146 D. 24 F F H-C (=O) OCH3 4-SCF3 CH3 148-154 D. 25 Cl H H-C (=O)-NHC6H4-4-F 4-OCF3 H 142-143 D. 26 Cl H H-C (=O)-CH3 4-OCF3 H 179-180 D. 27 Cl H H-C (=O)-OCH3 4-OCF3 H 211-212 D. 28 F F H-C (=O) CH3 4-OCF3 Et 186-187 D. 29 F F H-C (=O) OCH3 4-OCF3 Et 159-160 D. 30 F F H-C (=O)-NHC6H4-4-F 4-OCF3 Et 120-121 D. 31 F F H-C (=O) CH3 4-OCF3 n-Prop 176-177 D. 32 F F H-C (=O) OCH3 4-OCF3 n-Prop 154-155 D. 33 F F H-C (=O)-NHC6H4-4-F 4-OCF3 n-Prop Oil Table E: Compounds of formula X3 R3a R2 m.p. (°C) E. 1 F F H-C (=O) CH3 H 225-228 E. 2 F F H-C (=O) OCH3 H 200-206 E. 3 F F H-C (=O) OCH3 CH2NO2 202-204 E. 4 F F H-C (=O) OCH3 CH2 (CH3) NO2 179-183 E. 5 F F H-C (=O) CH3 CH2NO2 146-150 E. 6 F F H-C (=O) CH3 CH (CH3) NO2 198-201 E. 7 F F H H CH2NO2 207-210 E. 8 F F H H CH (CH3) NO2 218-228 E. 9 F F H H H 230-235 Table F: Compounds of formula X1 X2 X3 R3a R11 R12 R2 <BR> <BR> <BR> <BR> F. 1 Cl H F-C (=O) CH3 4-OCF3 H CH3 135-136 F. 2 Cl H F-C (=O) OCH2CH3 4-OCF3 H CH3 158-159 F. 3 F F H-C (=O) CH3 4-OCF3 2-OCH3 H 153-155 F. 4 F F H-C (=O) OCH3 4-OCF3 2-OCH3 H 150-154 F. 5 F F H-C (=O) CH3 4-OCF3 3-CH3 H 138-141 F. 6 F F H-C (=O) OCH3 4-OCF3 3-CH3 H 199-201 F. 7 F F H H 4-OCF3 2-OCH3 H 188-190 F. 8 F F H H 4-CF3 3-CH3 H 212-214 F. 9 F F H H 4-OCF3 3-CH3 H 204-206 F. 10 F F H-C (=O) CH3 4-CF3 3-CH3 H 165-167 F. 11 F F H-C (=O) OCH3 4-CF3 3-CH3 H 173-176 Table G: Compounds of formula X1 X2 X3 R2 Rr R3b m. p. (C) G. 1 F F H n-But Br n-But 106-116 G. 2 F F H H-C6H4-4-OCF3-C (=O) OCH3 170-180 G. 3 F F H H-OC6H4-4-OCF3-C (=O) CH3 137-139 G. 4 Cl H F H Br-C (=O) CH (Et)-n-But 160-162 G. 5 Cl H F H Br-C (=O) CH2CH3 191-193 G. 6 Cl H F H Br-C (=O) CH (Et)-n-But 140-143 G. 7 Cl H F H-C6H4-4-OCF3-C (=O)-i-Prop 186-188 G. 8 Cl H F H Br-C (=O)-NHC6H4-4-OCF3 Oil G. 9 Cl H F H Br -CH2-O-CH3 130-132 G. 10 Cl H F H-C6H4-4-OCF3-CH2-O-CH3 155-157 G. 11 Cl H F H-C6H4-4-OCF3-CH2-C6H4-4-CF3 Oil G. 12 F F H H-C6H4-4-OCF3-C (=O) CH (Et)-n-But 141-45 G. 13 Cl H F H -C6H4-4-OCF3 -CH2-C#CH 178-180 G. 14 Cl H F H-C6H4-4-OCF3-CH2-CH=CH2 189-191 G. 15 Cl H F H-C6H4-4-OCF3-CH2-CH3 245-248 G. 16 Cl H F H-C6H4-4-OCF3-CH3 251-253 G. 17 F H H H Br -CH2-O-CH3 126-128 G. 18 F H H H-C6H4-4-OCF3-CH2-O-CH3 147-149 G. 19 F H H H-C6H4-4-CF3-CH2-O-CH3 171-173 G. 20 Cl H H H-C6H4-4-OCF3-C (=O) CH3 165-166 G. 21 Cl H H H-C6H4-4-OCF3-C (=O) OCH3 170-172 G. 22 Cl H H H-C6H4-4-OCF3-CH2-O-CH3 150-153 G. 23 Cl H H H-C6H4-4-CF3-C (=O) CH3 170-173 G. 24 F H H H Br-CH2-CH3 116-118 G. 25 F H H H-C6H4-4-OCF3-CH2-CH3 164-166 G. 26 F H H H Br-CH2-CH=CH2 77-79 G. 27 F H H H Br-CH2-C=-CH 75-77 Xi X2 X3 R2 Rr m.p. (°C G. 28 F H H H-C6H4-4-CF3-CH2-CH3 173-175 G. 29 F H H H-C6H3-3, 5-CI2-CH2-CH3 136-138 G. 30 H H CF3 H Br -CH2-O-CH3 135-137 G. 31 H H CF3 H -C6H4-4-OCF3 -CH2-O-CH3 168-170 G. 32 H H CF3 H-C6H4-4-CF3-CH2-O-CH3 198-200 G. 33 Cl H H H-C6H4-4-CF3-CH2-O-CH3 166-170 G. 34 Cl H H H-C6H3-3, 5-Cl2 -C(=O) OCH3 135-137 G. 35 Cl H F H Br-CH2-CH3 167-169 G. 36 Cl H F H Br-CH2-OCH2CH3 120-122 G. 37 Cl H F H Br-CH2-C6H4-4-CF3 150-152 G. 38 Cl H F H Br-CH3 173-175 G. 39 F H H H Br-C (=O)-NHC6H4-4-OCF3 142-144 G. 40 F H H H Br-CH2-C6H4-4-CF3 128-130 G. 41 F H H H-C6H4-4-OCF3-CH2-C6H4-4-CF3 174-176 G. 42 F H H H-C6H4-4-CF3-CH2-C6H4-4-CF3 186-188 G. 43 F H H H-C6H3-3, 5-CI2-CH2-C6H4-4-CF3 154-156 G. 44 Cl H H H-C6H3-3, 5-CI2-CH2-OCH3 148-150 G. 45 Cl H H H Br-CH2-OCH3 115-117 G. 46 F H H H-C6H4-4-OCF3-CH2-C=-CH 140-142 G. 47 F H H H-C6H4-4-OCF3-CH2-CH2=CH2 145-147 G. 48 F H H H-C6H4-4-CF3-CH2-C-CH 158-161 G. 49 F H H H-C6H4-4-CF3-CH2-CH2=CH2 161-163 G. 50 F H H H-C6H3-3, 5-CI2-CH2-OCH3 162-164 G. 51 F H H H-C6H3-3,5-CI2-CH2-C=-CH 155-158 G. 52 F F H H-C6H3-3, 5-Cl2-CH2-CH2=CH2 120-122 G. 53 F F H H-C6H4-4-OCF3-CH2-CH3 151-153 G. 54 F F H H -C6H4-4-OCF3 -CH2-C#CH 155-158 G. 55 F F H H-C6H4-4-OCF3-CH2-OCH3 163-166 G. 56 F F H H -C6H4-4-OCF3 -CH2-C#N 177-183 G. 57 F F H H-C6H3-3, 5-Cl2 -CH2-OCH3 146-148 G. 58 F F H H-C6H4-4-CF3-CH2-CH3 175-179 G. 59 F F H H -C6H4-4-CF3 -CH2-C#CH 193-196 Xi X2 X3 R2 Rr R3b m.p. (°C) G. 60 F F H H-C6H4-4-CF3-CH2-OCH3 169-171 G. 61 Cl H H H-C6H4-4-CF3-CH2-CH3 248-252 G. 62 Cl H H H-C6H4-4-CF3-CH2-C--CH 163-166 G. 63 Cl H H H-C6H4-4-CF3-CH2-CH2=CH2 186-189 Table H: Compounds of formula Rsa Rn R2 m.p. (°C) <BR> <BR> <BR> <BR> H. 1-C (=O) CH3 H CH2NO2 165-168 H. 2-C (=O) OCH3 H CH2NO2 198-201 H. 3-C (=O) CH3 H H 198-199 H. 4-C (=O) OCH3 H H 241-244 H. 5 H H H 216-218 H. 6 H H CH2NO2 191-193 The compounds of formula of formula of formula of formula Isomeric mixtures of the compounds of formulae and isomeric mixtures of the compounds of formulae The compound of the formula Formulation Examples for use in crop protection (throughout, percentages are by weight) Example F1 : Emulsifiable concentrates a) b) c) active ingredient 25% 40% 50% calcium dodecylbenzenesulfonate 5% 8% 6% castor oil polyethylene glycol ether (36 mol EO) 5% tributylphenol polyethylene glycol ether (30 mol EO)-12% 4% cyclohexanone-15% 20% xylene mixture 65% 25% 20% The finely ground active ingredient and adjuvants are mixed to give an emulsifiable concentrate which yields emulsions of any desired concentration when diluted with water.

Example F2: Solutions a) b) c) d) active ingredient 80% 10% 5% 95% ethylene glycol monomethyl ether 20% - - - polyethylene glycol (MW 400)-70% N-methylpyrrolid-2-one-20%-- epoxidised coconut oil--1 % 5% petrol ether (boiling range: 160-190°)--94% The finely ground active ingredient and adjuvants are mixed to yield a solution suitable for use in the form of microdrops.

Example F3: Granules a) b) c) d) active ingredient 5% 10% 8% 21% kaolin 94%-79% 54% highly dispersed silicic acid 1 %-13% 7% attapulgite-90%-18% The active ingredient is dissolved in dichloromethane, the solution is sprayed onto the carrier mixture and the solvent is removed by evaporation in vacuo.

Example F4: Wettable powders a) b) c) active ingredient 25% 50% 75% sodium lignosulfonate 5% 5% sodium lauryl sulfate 3%-5% sodium diisobutylnaphthalenesulfonate-6% 10% octylphenol polyethylene glycol ether (7-8 mol EO)-2% highly dispersed silicic acid 5% 10% 10% kaolin 62% 27%- The active ingredient and adjuvants are mixed and the mixture is ground in a suitable mill, affording wettable powders which can be diluted with water to give suspensions of any desired concentration.

Example F5: Emulsifiable concentrate active ingredient 10% octylphenol polyethylene glycol ether (4-5 mol EO) 3% calcium dodecylbenzenesulfonate 3% castor oil polyethylene glycol ether (36 mol EO) 4% cyclohexanone 30% xylene mixture 50% The finely ground active ingredient and the adjuvants are mixed to yield an emulsifiable concentrate which gives emulsions of any desired concentration when diluted with water.

Example F6: Extruder granules active ingredient 10% sodium lignosulfonate 2% carboxymethylcellulose 1 % kaolin 87% The active ingredient and adjuvants are mixed, the mixture is ground, moistened with water, extruded and granulated, and the granules are dried in a stream of air.

Example F7: Coated qranules active ingredient 3% polyethylene glycol (MW 200) 3% kaolin 94% The finely ground active ingredient is uniformly applied, in a mixer, to the kaolin moistened with polyethylene glycol to yield non-dusty coated granules.

Example F8: Suspension concentrate active ingredient 40% ethylene glycol 10% nonylphenol polyethylene glycol ether (15 mol EO) 6% sodium lignosulfonate 10% carboxymethylcellulose 1 % aqueous formaldehyde solution (37 %) 0.2% aqueous silicone oil emulsion (75 %) 0.8% water 32% The finely ground active ingredient and adjuvants are mixed, giving a suspension con- centrate from which suspensions of any desired concentration can be obtained by dilution with water.

Biological Examples: Example B1 : Action against Aphis craccivora Pea seedlings are infested with Aphis craccivora, subsequently sprayed with a spray mixture comprising 100 ppm of active ingredient and then incubated at 20°C. 3 and 6 days later the percentage reduction in population (% activity) is determined by comparing the number of dead aphids on the treated plants with that on untreated plants.

Compounds of the Tables exhibit good activity in this test.

Example B2: Action against Diabrotica balteata Maize seedlings are sprayed with an aqueous emulsion spray mixture comprising 100 ppm of active ingredient. After the spray-coating has dried, the maize seedlings are populated with 10 Diabrotica balteata larvae in the second stage and then placed in a plastics container. 6 days later, the percentage reduction in population (% activity) is determined by comparing the number of dead larvae on the treated plants with that on untreated plants.

Compounds of the Tables exhibit good activity in this test. For example, compounds B. 5, B. 12 and B. 18, in particular, exhibit a reduction in the pest population of more than 80 %.

Example B3: Action against Heliothis virescens Young soybean plants are sprayed with an aqueous emulsion spray mixture comprising 100 ppm of active ingredient. After the spray-coating has dried, the plants are populated with 10 caterpillars of Heliothis virescens in the first stage and then placed in a plastics container. 6 days later, the percentage reduction in population and in feeding damage (% activity) are determined by comparing the number of dead caterpillars and the feeding damage on the treated plants with that on untreated plants.

Compounds of the Tables exhibit good activity in this test. For example, compounds B. 2, B. 3, B. 12, B. 13 and B. 18, in particular, exhibit a reduction in the pest population of more than 80 %.

Example B4: Action against Spodoptera littorals Young soybean plants are sprayed with an aqueous emulsion spray mixture comprising 100 ppm of active ingredient. After the spray-coating has dried, the plants are populated with 10 caterpillars of Spodoptera littorals in the third stage and then placed in a plastics container. 3 days later, the percentage reduction in population and the percentage reduction in feeding damage (% activity) are determined by comparing the number of dead caterpillars and the feeding damage on the treated plants with that on untreated plants.

Compounds of the Tables exhibit good activity in this test. For example, compounds B. 1, B. 3, B. 4, B. 5, B. 10 to B. 14 and B. 18, in particular, exhibit a reduction in the pest population of more than 80 %.

Example B5: Action against Nilaparvata lugens Rice plants are treated with an aqueous emulsion spray mixture comprising 400 ppm of active ingredient. After the spray-coating has dried, the rice plants are populated with cicada larvae in the 2nd and 3rd stages. The evaluation is carried out 21 days later. The percentage reduction in population (% activity) is determined by comparing the number of surviving cicadas on the treated plants with that on untreated plants.

Compounds of the Tables exhibit good activity in this test. For example, compounds B. 12 and B. 18, in particular, exhibit a reduction in the pest population of more than 80 %.

Example B6: Action against Tetranychus urticae Young bean plants are populated with a mixed population of Tetranychus urticae and sprayed one day later with an aqueous emulsion spray mixture comprising 100 ppm of active ingredient. The plants are then incubated for 6 days at 25°C and subsequently evaluated.

The percentage reduction in population (% activity) is determined by comparing the number of dead eggs, larvae and adults on the treated plants with that on untreated plants.

The compounds of the Tables exhibit good activity in this test. For example, compounds B. 11, B. 12, B. 13 and B. 18, in particular, exhibit a reduction in the pest population of more than 80 %.