Pesticidally active tetrazine derivatives The present invention relates to compounds of formula wherein T-V is-N=N-or-NH-NH- ; X1 R1; X2 and X3 are each independently of the other H or Ri; R1 is halogen, CN, C3-C8cycloalkyl,C1-C6haloalkyl,C3-C8halocycloalkyl,C1-6alkyl , C1-C6haloalkoxy,C3-C8halocycloalkoxy,C1-C6alkylthio,C1-C6alk oxy,C3-C8cycloalkoxy, C3-C8cycloalkylthio, C,-C6haloalkytthio or C3-C8halocycloalkylthio; Ar, is unsubstituted or mono-to tetra-substituted aryl or heteroaryl, the substituents being selected from the group consisting of OH, halogen, CN, NOs, C1-C6alkyl, C3-C8cycloalkyl, C1-C6haloalkyl,C3-C8halocycloalkyl,C1-C6alkyl-C3-C8cycloalky l,C3-C8cycloalkyl-C1-C6alkyl, C1-C6alkoxy, C3-C8cycloalkoxy, C1-C6alkylthio,C3-c8halocycloalkoxy, C3-C8halocycloalkylthio,C1-C6alkylsulfinyl,C3-C8-C3-C8cycloa lkylthio,C1-C6haloalkylthio, cycloalkylsulfinyl,C1-C6alkylsulfonyl,C3-C8halocycloalkylsul finyl, C3-C8halocycloalkylsulfonyl,C2-C8alkenyl,C3-c8cycloalkylsulf onyl,C1-C6haloalkylsulfonyl, C1-C6alkyl-C(=NOR2)andR3;C2-C8alkynyl,C1-C6alkylcarbonyl, Ar2 is unsubstituted or mono-to penta-substituted aryl or heteroaryl, the substituents being selected from the group consisting of OH, halogen, CN, NO2, C1-C6alkyl, C3-C8cycloalkyl, <BR> <BR> C,-C6alkyl-C3-C8cycloalkyl, C3-Cecycloalkyl-C,-Csalkyl, C,-C6haloalkyl, C3-Cehalocycloalkyl, C1-C6haloalkoxy,C3-C8halocycloalkoxy,C1-C6alkylthio,C1-C6alk oxy,C3-C8cycloalkoxy, C3-C8halocycloalkylthio,C1-C6alkylsulfinyl,C3-C8cyc-C3-C8cyc loalkylthio,C1-C6haloalkylthio, <BR> <BR> loalkylsulfinyl, C,-C6haloalkylsulfinyl, C3-Cehalocycloalkylsulfinyl, C,-C6alkylsulfonyl,<BR> <BR> C3-C8cycloalkylsulfonyl, C,-C6haloalkylsutfonyl, C3-Cshalocycloalkylsulfonyl, C2-C8alkenyl, C2-C8alkynyl, C,-C6alkylcarbonyl, C,-C6alkyl-C (=NOR2) and R3; A is a single bond, C,-C, 2alkylene, O, O (C,-C, 2alkylene), S (O) n, S (O) n (C1-12alkylene), C2-C8alkenylene, C2-C8alkynylene ; NR6, NR6 (C,-C, 2alkylene) or C(=Z); Z is O, NR4, NNR4R5 or NOR4; R2 is H, C,-C6alkyl or C3-C8cycloalkyl; R4 and R5 are each independently of the other H, C,-C6alkyl or C,-C6haloalkyl; R6 is H, C,-C6alkyl, C3-C8cycloalkyl, C,-C6haloalkyl, C2-C8alkenyl, C2-Csalkynyl, aryl- C,-C6alkyl, (CH2) pC (O) R7 or C-C6alkoxy-C2-C6alkyl; R7 is H, C,-C6alkyl, C3-C8cycloalkyl, C,-C6haloalkyl, C,-C6alkoxy, N (R8) 2 or C,-C6alkoxy-C2-C6alkyl; R8 is H, C,-C6alkyl, C3-C8cycloalkyl, C1-C6haloalkyl or aryl-C,-C6alkyl; Rg and R10 are each independently of the other H or C,-C6alkyl; m is 1,2,3 or 4; n is 0,1 or 2; p is 0, and Q is O or S; with the proviso, that when T-V is-NH-NH-, X, is halogen, X2 and X3 are both hydrogen, Ar, and Ar2 are both phenyl which may be unsubstituted or substituted, A is not a single bond; or, where applicable, a possible E/Z isomer, mixture of E/Z isomers and/or tautomer thereof, in each case in free form or in salt form, to a process for the preparation of those com- pounds and to the use thereof, to pesticidal compositions in which the active ingredient is selected from those compounds, in each case in free form or in agrochemically acceptable salt form, and to a process for the manufacture of those compositions and to their use.

Certain 1,2,4,5-triazine derivatives are proposed in the literature as active ingredients in compositions for controlling pests on domestic animals and productive livestock and in crops of useful plants. The biological properties of those known compounds are not entirely satis- factory in the field of pest control, however, for which reason there is a need to provide further compounds having pesticidal properties, that problem being solved according to the invention by the provision of the present compounds of formula (I).

The compounds of formula (I) may be in the form of salts or may form e. g. acid addition salts. The latter 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, e. g. halo-substituted, C,-C4alkanecarboxylic acids, for example acetic acid, saturated or unsaturated dicarboxylic acids, e. g. oxalic, malonic, maleic, fumaric or phthalic acid, hydroxycarboxylic acids, e. g. ascorbic, lactic, malic, tartaric or citric acid, or benzoic acid, or with organic sulfonic acids, such as unsubstituted or substituted, e. g. halo-substituted, C,-C4alkane-or aryl-sulfonic acids, e. g. methane-or p- toluene-sulfonic acid. Furthermore, compounds of formula (1) having at least one acid group may form 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. ethyl-, diethyl-, triethyl-or dimethyl-propyl-amine, or a mono-, di-or tri-hydroxy-lower alkylamine, e. g. mono-, di-or tri-ethanolamine. It may also be possible for corresponding internal salts to be formed. Within the scope of the invention preference is given to agrochemically advantageous salts; also included, however, are other salts, which can be used, for example, for the isolation or purification of free compounds of formula (I) or the agrochemically acceptable salts thereof.

Hereinabove and hereinbelow any reference to the free compounds of formula (I) or to their salts is to be understood as including also the corresponding salts or the free compounds of formula (I), respectively, as appropriate and expedient. The free form is preferred.

The general terms used hereinabove and hereinbelow have the meanings given below, unless defined otherwise.

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

Aryl is phenyl or naphthyl, preferably phenyl.

Heteroaryl is pyridyl, pyrimidyl, s-triazinyl, 1,2,4-triazinyl, thienyl, furanyl, pyrryl, pyrazolyl, imidazolyl, thiazolyl, triazolyl, oxazolyl, thiadiazolyl, oxadiazolyl, benzothienyl, benzofuranyl, benzothiazolyl, indolyl or indazolyl, preferably pyridyl, pyrimidyl, s-triazinyl or 1,2,4-triazinyl, especially pyridyl.

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

Cycloalkyl-as a group per se and as a structural element of other groups and compounds, such as halocycloalkyl, cycloalkoxy and cycloalkylthio-is, in each case giving due consider- ation to the number of carbon atoms contained in the group or compound in question, cyclo- propyl, 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 contained in the group or compound in question, either straight- chained, 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 contained in the group or compound in question, either straight- chained, e. g. propargyl, 2-butynyl, 3-pentynyl, 1-hexynyl, 1-heptynyl, 3-hexen-1-ynyl or 1,5- heptadien-3-ynyl, or branched, e. g. 3-methylbut-1-ynyl, 4-ethylpent-1-ynyl, 4-methylhex-2- ynyl or 2-methylhept-3-ynyl.

Alkylene, alkenylene and alkynylene are straight-chained or branched hydrocarbon bridges, especially-CH2-,-CH2-CH2-,-CH (CH3)-,-CH (CH3) CH2-,-CH (CH3) CH2-CH2-, -CH2C (CH3) 2-CH2-,-CH=CH-,-CH2-CH=CH-,-CH2-CH=CH-CH2-;-C-C-and-CH2C_C-; more especially-CH2-.

Halo-substituted carbon-containing groups and compounds, such as haloalkyl, haloalkoxy and haloalkylthio, may be partially halogenated or perhalogenated, the halogen substituents in the case of polyhalogenation 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 halo- alkoxy and haloalkylthio-are methyl substituted from one to three times by fluorine, chlorine and/or bromine, such as CHF2 or CF3; ethyl substituted from one to five times by fluorine, chlorine and/or bromine, such as CH2CF3, CF2CF3, CF2CCI3, CF2CHCI2, CF2CHF2, CF2CFCI2, CF2CHBr2, CF2CHCIF, CF2CHBrF or CCIFCHCIF; propyl or isopropyl substituted from one to seven times by fluorine, chlorine and/or bromine, such as CH2CHBrCH2Br, CF2CHFCF3, CH2CF2CF3 or CH (CF3) 2; butyl or an isomer thereof substituted from one to nine times by fluorine, chorine and/or 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 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 bromine, such as (CH2) 4CHBrCH2Br, CF2 (CHF) 4CF3, CH2 (CF2) 4CF3 or C (CF3) 2 (CHF) 2CF3.

Preference is given to compounds of formula (I) wherein X, is R, ; X2 and X3 are each independently of the other H or Ri; R, is halogen, CN, N02, C,-C6alkyl, C3-C8cycloalkyl, C,-C6haloalkyl, C3-C8halocycloalkyl, C1-C6haloalkoxy,C3-C8halocycloalkoxy,C1-C6alkylthio,C1-C6alk oxy,C3-C8cycloalkoxy, C3-C8cycloalkylthio, C1-C6haloalkylthio, or C3-C8halocycloalkylthio; Ar, is unsubstituted or mono-to tetra-substituted aryl or heteroaryl, the substituents being selected from the group consisting of OH, halogen, CN, NO2, C1-C6alkyl, C3-C8cycloalkyl, <BR> <BR> <BR> C,-C6alkyl-C3-C8cycloalkyl, C3-C8cycloalkyl-C-C6alkyl, C,-Cshaloalkyl, C3-C8halocycloalkyl,<BR> <BR> <BR> <BR> <BR> C,-Csalkoxy, C3-C8cycloalkoxy, C,-C6haloalkoxy, C3-C8halocycloalkoxy, C,-C6alkylthio, C3-C8cycloalkylthio, C1-C6alkylsulfinyl,C3-C8halocycloalkylthio, C3-Cscycloalkylsulfinyl, C1-C6haloalkylsulfinyl, C3-C8halocycloalkylsulfinyl, C,-C6alkylsulfonyl, C3-C8halocycloalkylsulfonyl,C2-C8alkenyl,C3-C8cycloalkylsulf onyl,C1-C6haloalkylsulfonyl, C2-C8alkynyl, C1-C6alkylcarbonyl, C1-C6alkyl-C(=NOR2) and R3; Ar2 is unsubstituted or mono-to penta-substituted aryl or heteroaryl, the substituents being selected from the group consisting of OH, halogen, CN, NO2, C,-C6alkyl, C3-Cecycloalkyl, <BR> <BR> <BR> C,-C6alkyl-C3-Cecycloalkyl, C3-C8cycloalkyl-C,-C6alkyl, C,-C6haloalkyl, C3-CBhalocycloalkyl,<BR> <BR> <BR> <BR> <BR> C-Csalkoxy, C3-C8Cycloalkoxy, C,-C6haloalkoxy, C3-Cehalocycloalkoxy, C,-C6alkylthio, C3-C8halocycloalkylthio,C1-C6alkylsulfinyl,C3-C8cycloalkylth io,C1-C6haloalkylthio, C3-C8halocycloalkylsulfinyl,C1-C6alkylsulfonyl,C3-C8cycloalk ylsulfinyl,C1-C6haloalkylsulfinyl, C3-C8cycloalkylsulfonyl, C,-C6haloalkylsulfonyl, C3-C8halocycloalkylsulfonyl, C2-C8alkenyl, C2-C8alkynyl, C1-C6alkylcarbonyl, C1-C6alkyl-C(=NOR2) and R3; A is (CR4R5) p, O (CR4R5) p, S (O) n (CR4R5) p, unsubstituted or substituted C2-Csalkenylene, unsubstituted or substituted C2-Cealkynylene, the substituents in each case being selected from the group consisting of R4 and Rs, or NR6 (CH2) p or C (=Z); Z is 0, NR4, NNR4R5 or NOR4; R2 is H, C3-C8cycloalkyl;or R4 and R5 are each independently of the other H, C1-C6alkyl or C,-C6haloalkyl; R6 is H, C1-C6alkyl, C3-C8cycloalkyl, C,-C6haloalkyl, C2-Cealkenyl, C2-C8alkynyl, aryl- C1-C6alkyl, (CH2) pC (O) R7 or C,-C6alkoxy-C2-C6alkyl; H,C1-C6alkyl,C3-C8cycloalkyl,C1-C6haloalkyl,C1-C6alkoxy,N(R8 )2orC1-C6alkoxy-R7is C2-C6alkyl; R8 is H, C1-C6alkyl, C3-C8cycloalkyl, C1-C6haloalkyl or aryl-C,-C6alkyl; Ra and R o are each independently of the other H or C,-C6alkyl; m is 1,2,3 or 4; n is 0,1 or 2; p is 0,1,2,3,4,5 or 6; and Q is O or S.

Especially preferred embodiments within the scope of the invention are (1) a compound of formula (I), wherein X2 is Ri; (2) a compound according to group (1) above of formula (I), wherein X3 is H; (3) a compound according to anyone of the groups (1) or (2) above of formula (I), wherein R, is halogen, C,-C4alkyl, C3-C8cycloalkyl, C,-C4haloalkyl, C,-C4alkoxy, C,-C4haloalkoxy, C,-C4alkylthio or Ci-C4haloalkylthio; especially halogen, C1-C2alkyl, C1-C2haloalkyl, C1-C2- alkoxy or C,-C2haloalkoxy; more especially fluorine, chlorine, methyl, trifluoromethyl or methoxy; (4) a compound according to anyone of the groups (1) to (3) above of formula (I), wherein Ar1 is unsubstituted or mono-or di-substituted aryl or heteroaryl, the substituents being selected from the group consisting of OH, halogen, CN, N02, C1-C4alkyl, C3-C8cycloalkyl, C1-C4haloalkyl,C3-C6halocycloalkyl,C1-C4alkyl-C3-C4cycloalky l,C3-C8cycloalkyl-C1-C4alkyl, C1-C4haloalkoxy,C3-C6halocycloalkoxy,C1-C4alkylthio,C1-C4alk oxy,C3-C6cycloalkoxy, C3-C6cycloalkylthio,C1-C4alkylsulfinyl,C3-C6-C3-C6halocycloa lkylthio, C3-C6halocycloalkylsulfinyl,C1-C4alkuylsulfonyl,cycloalkylsu lfinyl,C1-C4haloalkylsulfinyl, C3-C6halocycloalkylsulfonyl,C2-C6alkenyl,C3-C6cycloalkylsulf onyl,C1-C4haloalkylsulfonyl, C2-C6alkynyl, C1-C4alkylcarbonyl, C1-C4alkyl-C (=NOR2) and R3; especially unsubstituted or mono-or di-substituted aryl or heteroaryl, the substituents being selected from the group consisting of OH, halogen, CN, NO2, C,-C4alkyl, C3-C6cycloalkyl, C1-C4haloalkyl, C1-C4- alkoxy, C1-C4haloalkylthio,C2-C6alkenyl,C2-C6alkynylandC1-C4alkylthi o, C,-C4alkylcarbonyl; more especially unsubstituted or mono-substituted pyridyl or phenyl, the substituents being selected from the group consisting of halogen, C1-C4alkyl, C1-C4haloalkyl, C,-C4alkoxy, C,-C4haloalkoxy, C,-C4alkylthio and C,-C4haloalkylthio; preferably unsubstituted or mono-substituted phenyl, the substituents being selected from the group consisting of methyl, trifluoromethyl, methoxy, trifluoromethoxy and chlorine; most preferably unsub- stituted phenyl; (5) a compound according to anyone of the groups (1) to (4) above of formula (I), wherein Ar2 is unsubstituted or mono-to tri-substituted aryl or heteroaryl, the substituents being selected from the group consisting of OH, halogen, CN, NO2, C1-C4alkyl, C3-C6cycloalkyl, C1-C4haloalkyl,C3-C8halocycloalkyl,C1-C4alkyl-C3-C4cycloalky l,C3-C8cycloalkyl-C1-C4alkyl, C1-C4haloalkoxy,C3-C6halocycloalkoxy,C1-C4alkylthio,C1-C4alk oxy,C3-C6cycloalkoxy, C3-C6halocycloalkylthio,C1-C4alkylsulfinyl,C3-C6-C3-C6cycloa lkylthio,C1-C4haloalkylthio, C3-C6halocycloalkylsulfinyl,C1-C4alkylsulfonyl,cycloalkylsul finyl,C1-C4haloalkylsulfinyl, C3-Cscycloalkylsulfonyl, C,-C4haloalkylsulfonyl, C3-C6halocycloalkylsulfonyl, C2-C6alkenyl, C2-C6alkynyl, C1-C4alkylcarbonyl, C1-C4alkyl-C(=NOR2) and R3; especially unsubstituted or mono-or di-substituted aryl or heteroaryl, the substituents being selected from the group consisting of OH, halogen, CN, NO2, C,-C4alkyl, C3-C6cycloalkyl, C,-C4haloalkyl, C,-C4- alkoxy, C1-C4haloalkylthio,C2-C6alkenyl,C2-C6alkynyl,andC1-C4alkylth io, C,-C4alkylcarbonyl; more especially unsubstituted or mono-substituted phenyl, the substit- uents being selected from the group consisting of halogen, C,-C4alkyl, C,-C4haloalkyl, C,-C4alkoxy, C,-C4haloalkoxy, C,-C4alkylthio and C,-C4haloalkylthio; most preferably substituted phenyl, the substituents being selected from the group consisting of fluorine, chlorine, C,-C4alkyl, trifluoromethyl, methoxy, trifluoromethoxy and methylthio; (6) a compound according to anyone of the groups (1) to (5) above of formula (I), wherein A is -CH2-, -O-CH2-, C2-C4alkenylene, C2-C4alkynylene or NR3; especially a single bond,-CH2-, O, CH=CH, C_C or NH; more especially-CH2-or a single bond; very preferably a single bond; (7) a compound according to anyone of the groups (1) to (6) above of formula (I), wherein Z is O; (8) a compound according to anyone of the groups (1) to (7) above of formula (I), wherein R2 is H or C,-C2alkyl, especially H or methyl; (9) a compound according to anyone of the groups (1) to (8) above of formula (I), wherein R4 and Rs are each independently of the other H or C1-C2alkyl, especially H or methyl; (10) a compound according to anyone of the groups (1) to (9) above of formula (I), wherein R6 is H, C1-C4alkyl, C3-C6cycloalkyl or C1-C4haloalkyl, especially H or C,-C2alkyl; (11) a compound according to anyone of the groups (1) to (10) above of formula (I), wherein 0or1;nis (12) a compound according to anyone of the groups (1) to (11) above of formula (I), wherein p is 0,1,2,3 or 4, especially 0,1 or 2, more especially 0; (13) a compound according to anyone of the groups (1) to (12) above of formula (I), wherein X2 is Ri; X3 is H; R1 is halogen, C,-C4alkyl, C3-C6cyctoalkyl, C,-C4haloalkyl, C,-C4alkoxy, C,-C4haloalkoxy, C,-C4alkylthio or C,-C4haloalkylthio; Ar, is unsubstituted or mono-or di- substituted aryl or heteroaryl, the substituents being selected from the group consisting of OH, halogen, CN, N02, C1-C4alkyl, C3-C6cycloalkyl, C1-C4alkyl-C3-C4cycloalkyl, C3-C6- C3-C6halocycloalkyl,C1-C4alkoxy,C3-C6cycloalkoxy,cycloalkyl- C1-C4alkyl,C1-C4haloalkyl, <BR> <BR> <BR> <BR> C,-C4haloalkoxy, C3-C6halocycloalkoxy, C-C4alkylthio, C3-C6cycloalkylthio, C,-C4halo-<BR> <BR> <BR> <BR> <BR> <BR> <BR> <BR> alkylthio, C3-C6halocycloalkylthio, C,-C4alkylsulfinyl, C3-C6cycloalkylsulfinyl, C,-C4haloalkyl-<BR> <BR> <BR> <BR> <BR> <BR> <BR> <BR> sulfinyl, C3-C6halocycloalkylsulfinyl, C,-C4alkylsulfonyl, C3-C6cycloalkylsulfonyl, C,-C4halo-<BR> <BR> <BR> <BR> <BR> <BR> <BR> <BR> alkylsulfonyl, C3-Cshalocycloalkylsulfonyl, C2-C6alkenyl, C2-C6alkynyl, C,-C4alkylcarbonyl, C,-C4alkyl-C (=NOR2) and R3; Ar2 is unsubstituted or mono-to tri-substituted aryl or hetero- aryl, the substituents being selected from the group consisting of OH, halogen, CN, N02, C1-C4alkyl-C3-C4cycloalkyl,C3-C6cycloalkyl-C1-C4alkyl,C1-C4a lkyl,C3-C6cycloalkyl, C1-C4alkoxy,C3-C6cycloalkoxy,C1-C4haloalkoxy,C1-C4haloalkyl, C3-C6halocycloalkyl, C3-C6halocycloalkoxy, C1-C4haloalkylthio,C3-C6halo-C3-C6cycloalkylthio, cycloalkylthio, C1-C4haloalkylsulfinyl,C3-C6halo-C3-C6cycloalkylsulfinyl, C3-C6cycloalkylsulfonyl,C1-C4haloalkylsulfonyl,cycloalkylsul finyl,C1C4alkylsulfonyl, C2-C6alkynyl,C1-C4alkylcarbonyl,C1-C4alkyl-C3-C6halocycloalk ylsulfonyl,C2-C6alkenyl, C (=NOR2) and R3; and A is a single bond, (CH2), O (CH2), C2-C4alkenylene, C2-C4alkynylene or NR3; (14) a compound according to anyone of the groups (1) to (13) above of formula (I), wherein X2 is Ri; X3 is H; R, is halogen, C,-C2alkyl, C1-C2haloalkyl, C1-C2alkoxy or C,-C2haloalkoxy; Arl is unsubstituted or mono-or di-substituted aryl or heteroaryl, the substituents being selected from the group consisting of OH, halogen, CN, N02, C1-C4alkyl, C3-C6cycloalkyl, C,-C4haloalkyl, C,-C4alkoxy, C,-C4haloalkoxy, C,-C4alkylthio, C,-C4haloalkylthio, C2-C6alkenyl, C2-C6alkynyl and C,-C4alkylcarbonyl; Ar2 is unsubstituted or mono-or di- substituted aryl or heteroaryl, the substituents being selected from the group consisting of OH, halogen, CN, NO2, C,-C4alkyl, C3-C6cycloalkyl, C,-C4haloalkyl, C,-C4alkoxy, C,-C4halo- alkoxy, C,-C4alkytthio, C,-C4haloalkylthio, C2-C6alkenyl, C2-C6alkynyl and C,-C4alkylcarbonyl; and A is a single bond, CH2, O, C=C, CH=CH or NH; (15) a compound according to anyone of the groups (1) to (14) above of formula (I), wherein X2 is Ri; X3 is H; R, is fluorine, chlorine, methyl, trifluoromethyl or methoxy; Ar, is an unsubstituted or mono-substituted pyridyl or phenyl ring, the substituents being selected from the group consisting of halogen, C,-C4alkyl, C,-C4haloalkyl, C,-C4alkoxy, C,-C4halo- alkoxy, C,-C4alkylthio and C,-C4haloalkylthio; Ar2 is unsubstituted or mono-substituted phenyl, the substituents being selected from the group consisting of halogen, C,-C4alkyl, C,-C4haloalkyl, C,-C4alkoxy, C,-C4haloalkoxy, C,-C4alkylthio and C,-C4haloalkylthio; and A is a single bond; (16) a compound according to anyone of the groups (1) to (15) above of formula (I), wherein the group T-V is-N=N- ; (17) a compound according to anyone of the groups (1) to (15) above of formula (I), wherein the group T-V is-NH-NH- ; (18) a compound according to anyone of the groups (1) to (17) above of formula (I), wherein X, and X2 are halogen and X3 is H; especially X, and X2 are fluorine or chlorine; especially X, is fluorine and X2 is fluorine or chlorine; particularly X, and X2 are fluorine; (19) a compound according to anyone of the groups (3) to (17) above of formula (I), wherein X, and X3 are halogen and X2 is H; especially X, and X3 are fluorine or chlorine; especially X, is chlorine and X3 is fluorine or chlorine; particularly X, is chlorine and X3 is fluorine; (20) a compound according to anyone of the groups (3) to (17) above of formula (I), wherein X, is fluorine, X2 is H and X3 is chlorine; in each case including the physiologically tolerable addition compounds.

Within the scope of the invention preference is given especially to the compounds of formula (I) listed in Tables 1 to 5 and more especially to the compounds of formula (I) mentioned in the Synthesis Examples.

The invention relates also to a process for the preparation of compounds of formula (I), in each case in free form or in salt form, which process comprises, for example, a) reacting a compound of formula which compounds are known or can be prepared analogously to corresponding known compounds and in which Xi, X2 and X3 are as defined for formula (I) and Q, is a leaving group, optionally in the presence of a catalyst, with a compound of formula respectively, which compounds are known or can be prepared analogously to corresponding known compounds and in which Arl, A and Ar2 are as defined for formula (I) and Q, is a leaving group, reacting the resulting product, optionally after isolation thereof, with a chlorinating agent, reacting the resulting chlorination product, optionally after isolation thereof again, with hydrazine, and reacting the resulting dihydrotetrazine derivative, optionally after isolation thereof again, with an oxidising agent, or b) for the preparation of a compound of formula (I) wherein A is a single bond, reacting in accordance with process a) a compound of formula (II) with a compound of formula which compounds are known or can be prepared analogously to corresponding known compounds and in which Ar, is as defined for formula (I) and Q, and Q2 are leaving groups, and reacting the resulting product with a compound of formula which compound is known or can be prepared analogously to corresponding known compounds and in which Ar2 is as defined for formula (I), and in each case, if desired, converting a compound of formula (I), in each case in free form or in salt form, obtainable in accordance with the process or by another method into a different compound of formula (I), separating a mixture of isomers obtainable in accordance with the process and isolating the desired isomer and/or converting a free compound of formula (I) obtainable in accordance with the process into a salt or converting a salt of a compound of formula (I) obtainable in accordance with the process into the free compound of formula (I) or into a different salt.

Variant a): The reactants can be reacted with one another as such, that is to say without the addition of a solvent or diluent, for example in the molten state. Generally, however, it is advantageous to add an inert solvent or diluent or a mixture thereof. Examples of solvents and diluents include: aromatic, aliphatic and alicyclic hydrocarbons and halogenated hydrocarbons, such as benzene, toluene, xylene, mesitylene, Tetralin, chlorobenzene, dichlorobenzene, bromo- benzene, petroleum ether, hexane, cyclohexane, dichloromethane, trichloromethane, tetra- chloromethane, dichloroethane, trichloroethene and tetrachloroethene; ethers, such as diethyl ether, dipropyl ether, diisopropyl ether, dibutyl ether, tert-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; amides, such as N, N-dimethylformamide, N, N-diethyl- formamide, N, N-dimethylacetamide, N-methylpyrrolidone and hexamethylphosphoric acid triamide; nitriles, such as acetonitrile and propionitrile; and sulfoxides, such as dimethyl sulfoxide.

Preferred leaving groups are halogens, tosylates, mesylates and triflates, especially halogens, more especially chlorine and bromine.

Suitable basic catalysts are tertiary amines and aza-aromatic compounds, preferably trialkylamines and substituted pyridines, especially triethylamine and 4-dimethylamino- pyridine.

Suitable chlorinating agents are (COCI) 2, SOCI2, S02CI2, PCI3, POC13 and PCI5, preferably PCI5.

Suitable oxidising agents are halogens, Oz and nitrite salts, preferably sodium nitrite.

The reactions are advantageously effected in a temperature range of from about 0°C to about +120°C, preferably from about 0°C to about +80°C.

In a preferred embodiment of variant a), a compound of formula (Ila) is reacted with a com- pound of formula (III) at from about 0° to about 30°, preferably about 10°, in a halogenated hydrocarbon, preferably methylene chloride, in the presence of a basic catalyst mixture, preferably a mixture of triethylamine and 4-dimethylaminopyridine; the resulting product is isolated, reacted with a chlorinating agent, preferably Pu) 5, at from about 80° to about 120°, preferably about 110°, in a halogenated hydrocarbon, preferably chlorobenzene, and the resulting chlorination product is then isolated again and reacted with hydrazine at about from 0° to 40°, preferably 20°, in an ether, preferably tetrahydrofuran; the resulting dihydro- tetrazine derivative is isolated and reacted with an oxidising agent, preferably sodium nitrite, at from about 0° to about 80°, preferably about 40°, in a water/acid mixture, preferably water/acetic acid, to form the tetrazine derivative.

Variant b): The reactants can be reacted with one another as such, that is to say without the addition of a solvent or diluent, for example in the molten state. Generally, however, it is advantageous to add an inert solvent or diluent or a mixture thereof. Examples of solvents and diluents are given in variant a).

Suitable leaving groups, basic catalysts, chlorinating agents and oxidising agents are those mentioned in variant a).

Suitable catalysts for the reaction with a compound of formula (V) are palladium complexes, e. g. tetrakis (triphenylphosphine) palladium.

In a preferred embodiment of variant b), a tetrazine derivative is first prepared in accordance with variant a) and is then reacted with a compound of formula (V) at about from 0° to 80°, preferably 50°, in an ether, preferably dimethoxyethane, in the presence of a catalyst, prefer- ably tetrakis (triphenylphosphine) palladium.

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 in a manner known per se into other salts of compounds of formula (I); for example, acid addition salts can be converted into other acid addition salts, for example by treatment of a salt of an inorganic acid, such as a hydrochloride, 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 that forms, for example silver chloride, is insoluble and thus precipitates out from the reaction mixture.

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

The compounds of formula (I) may also be obtained in the form of their hydrates and/or may include other solvents, for example solvents used for the crystallisation of compounds in solid form.

The invention relates to all those forms of the process in which a compound obtainable as starting compound 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 salt or, especially, is formed under the reaction conditions.

In the process of the present invention it is preferable to use those starting materials and intermediates which result in the compounds of formula (I) described at the beginning as being especially valable.

The invention relates especially to the processes described in the Preparation Examples.

The invention relates also to novel starting materials and intermediates, in each case in free form or in salt form, used according to the invention for the preparation of the compounds of formula (I) and their salts, to the use of those novel starting materials and intermediates and to processes for their preparation.

The invention relates especially also to compounds of formula wherein X,, X2, X3, Q1, Arl, A and Ar2 are as defined above, to the use thereof and to pro- cesses for their preparation. Furthermore, the compounds of formula (la) exhibit a spectrum of activity similar to that of compounds of formula (I) and can be used in the same manner.

The present invention relates also to the compounds of formula (la) as active ingredients and in respect of their use in agrochemical compositions.

In the area of pest control, the compounds of formula (I) according to the invention are active ingredients exhibiting valable preventive and/or curative activity with a very advantageous biocidal spectrum, even at low rates of concentration, while being well tolerated by warm- blooded animals, fish and plants. The active ingredients according to the invention 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. The insecticidal, ovicidal and/or acaricidal activity of the active ingredients according to the inven- tion may manifest itself directly, i. e. in the mortality of the pests, which occurs immediately or only after some time, for example during moulting, or of their eggs, or indirectly, for example in reduced oviposition and/or hatching rate, good activity corresponding to a mortality of at least 50 to 60 %.

The said animal pests include, for example, those mentioned in European Patent Application EP-A-736 252, page 5, line 55, to page 6, line 55. The pests listed therein are therefore included by reference in the subject matter of the present invention.

The compounds according to the invention can be used to control, i. e. to inhibit or destroy, pests of the mentioned type occurring especially on plants, more especially on useful plants and ornamentals in agriculture, in horticulture and in forestry, or on parts of such plants, such as the fruits, blossoms, leaves, stems, tubers or roots, while in some cases parts of plants that grow later are still protected against those pests.

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

The compounds according to the invention are especially suitable for controlling insects and representatives of the order Acarina, especially plant-destructive feeding insects, such as Anthonomus grandis, Diabrotica balteata, Heliothis virescens larvae, Plutella xylostella and Spodoptera littoralis larvae, and spider mites, such as Tetranychus spp., in cotton, fruit, citrus, maize, soybean, rape and vegetable crops.

The compositions according to the invention are also suitable for protecting plant propaga- tion material, e. g. seed, such as fruits, tubers or grains, or plant cuttings, against fungal infections and animal pests. The propagation material can be treated with the composition before planting: seed, for example, can be dressed before being sown. The active ingre- dients according to the invention can also be applied to grains (coating), either by impreg- nating the seeds in a liquid formulation or by coating them with a solid formulation. The composition 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 such methods of treating plant propagation material and to the plant propagation material so treated.

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 in the protection of warm-blooded animals, including farm animals, such as cows, pigs, sheep and goats, poultry, such as hens, turkeys and geese, animals bred for their fur, such as mink, foxes, chinchillas, rabbits and the like, and also domestic animals and pets, such as cats and dogs, and even human beings, against pests of the mentioned type.

For example, flea infestation in domestic animals and pets is a problem for the animal owner for which there is still no adequate solution. Owing to the complicated life cycle of the flea, none of the known methods of controlling fleas is totally satisfactory, especially since most of the known methods are aimed principally at controlling the fully grown fleas in the coat and take no account at all of the various juvenile stages of the fleas, which live not only in the animal's coat, but also on the floor, on carpets, on the animal's sleeping place, on chairs, in the garden and in all the other places with which the infested animal comes into contact.

Flea treatment is generally expensive and must be continued for prolonge periods, success generally being achieved only when the treatment is applied not only to the affected animal, e. g. the dog or cat, but also simultaneously to all the places frequented by the affected animal.

The compounds of formula (I) according to the invention can be used alone or in combina- tion with other biocides. For example, in order to enhance the effect they can be combined with pesticides having the same direction of action or in order to broaden the spectrum of activity they can be combined with substances having a different direction of action. Where it is desired to extend the spectrum of activity to endoparasites, e. g. worms, the compounds of formula (I) are advantageously combined with substances having endoparasiticidal properties. They can, of course, also be used in combination with anti-bacterial agents.

Especially suitable mixing partners are, for example: azamethiphos; chlorfenvinphos; cypermethrin, cypermethrin high-cis; cyromazine; diafenthiuron; diazinon; dichlorvos; dicrotophos; dicyclanil; fenoxycarb; fluazuron; furathiocarb; isazofos; iodofenphos; kinoprene; lufenuron; methacriphos; methidathion; monocrotophos; phosphamidon; profenofos; diofenolan; a substance obtainable from the Bacillus thuringiensis strain GC91 or from NCTC11821; pymetrozine; bromopropylate; methoprene; disulfoton; quinalphos; tau- fluvalinate; thiocyclam; thiometon; aldicarb; azinphos-methyl; benfuracarb; bifenthrin; buprofezin; carbofuran; dibutylaminothio; cartap; chlorfluazuron; chlorpyrifos; cyfluthrin; lambda-cyhalothrin; 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 containing insect-active nematodes; a preparation obtainable from Bacillus subtilis; a preparation containing insect- active fungi; a preparation containing insect-active viruses; AC 303 630; acephate; acrinathrin; alanycarb; alphamethrin; amitraz; AZ 60541; azinphos A; azinphos M; azo- cyclotin; bendiocarb; bensultap; beta-cyfluthrin; BPMC; brofenprox; bromophos A; bufen- carbe; butocarboxim; butylpyridaben; cadusafos; carbaryl; carbophenothion; chloethocarb; chlorethoxyfos; chlormephos; cis-res-methrin; clocythrin; clofentezine; cyanophos; cyclo- prothrin; cyhexatin; demeton-M; demeton-S; demeton-S-methyl; dichlofenthion; dicliphos; diethion; dimethoate; dimethylvinphos; dioxathion; edifenphos; emamectin; esfenvalerate; ethion; ethofenprox; ethoprophos; etrimphos; fenamiphos; fenbutatin oxide; fenothiocarb; fenpropathrin; fenpyrad; fenthion; fluazinam; flucycloxuron; flucythrinate; flufenoxuron; flufenprox; fonophos; fosthiazate; fubfenprox; HCH; hexaflumuron; hexythiazox; iprobenfos; isofenphos; isoxathion; ivermectin; lambda-cyhalothrin; malathion; mecarbam; mesulfen- phos; metaldehyde; metolcarb; milbemectin; moxidectin; naled; NC 184; omethoate; oxamyl; oxydemethon M; oxydeprofos; permethrin; phenthoate; phorate; phosmet; phoxim; pirimiphos M; pirimiphos A; promecarb; propaphos; prothiofos; prothoate; pyraclophos; pyrida-phenthion; pyresmethrin; pyrethrum; RH 5992; salithion; sebufos; sulfotep; sulprofos; tebufenpyrad; tebupirimphos; tefluthrin; temephos; terbam; tetrachlorvinphos; thiacloprid; thiamethoxam; thiafenox; thiodicarb; thiofanox; thionazin; thuringiensin; tralomethrin; triarathen; triazophos; triazuron; trichlorfon; triflumuron; trimethacarb; vamidothion; xylylcarb; YI 5301/5302; zetamethrin; DPX-MP062; RH-2485; D 2341 or XMC (3, 5-xylyl methyl- carbamate).

The good pesticidal activity of the compounds of formula (I) according to the invention corresponds to a mortality of at least 50-60 % of the mentioned pests.

The methods of applying the crop protection agents, i. e. the methods for controlling pests of said type, such as spraying, atomizing, dusting, coating, dressing, scattering or pouring (chosen in accordance with the intended objectives and prevailing circumstances), and the use of the compositions for controlling pests of said type are further objects of the invention.

Typical concentrations of active ingredient are between 0.1 and 1000 ppm, preferably between 0.1 and 500 ppm. The rates of application are generally 1 to 2000 g of active ingredient (a. i.) per hectare (ha = approximately 2.471 acres), especially 10 to 1000 g a. i./ha, and preferably 20 to 600 g a. i./ha.

The compounds of formula (I) are used in unmodified form or, preferably, together with the adjuvants conventionally employed in formulation technology and can therefore be formu- lated in known manner e. g. into emulsifiable concentrates, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granules, and also encapsulations in polymer substances. As with the nature of the compositions, the methods of application, such as spraying, atomising, dusting, scattering or pouring, are selected in accordance with the intended objectives and the prevailing circumstances and the invention relates also thereto.

The formulations, that is to say the compositions, preparations or mixtures comprising the compound (active ingredient) of formula (I), or a combination of that active ingredient with other agrochemical active ingredients and, as appropriate, a solid or liquid adjuvant, are prepared in known manner, e. g. by homogeneously mixing and/or grinding the active ingre- dients with extenders, for example with solvents, solid carriers, and optionally surface-active compounds (surfactants) and the invention relates also thereto.

As formulation auxiliaries there are used, for example, solid carriers, solvents, stabilisers, "slow release"auxiliaries, dyes and optionally surface-active substances (surfactants).

Suitable carriers and auxiliaries include all those substances customarily used in crop protection products. Suitable auxiliaries, such as solvents, solid carriers, surface-active compounds, non-ionic surfactants, cationic surfactants, anionic surfactants and other auxiliaries in the compositions used according to the invention, include e. g. those described in EP-A-736 252, page 7, line 51 to page 8, line 39; they are included by reference in the subject matter of the present invention.

Suitable anionic surfactants include both so-called water-soluble soaps and water-soluble synthetic surface-active compounds.

Suitable soaps are the alkali metal salts, alkaline earth metal salts or unsubstituted or substituted ammonium salts of higher fatty acids (C, 0-C22), e. g. the sodium or potassium salts of oleic or stearic acid, or of natural fatty acid mixtures which can be obtained e. g. from coconut oil or tall oil. Mention may also be made of fatty acid methyitaurine salts as surfactants.

More frequently, however, so-called synthetic surfactants are used, as mentioned in EP-A-736 252, especially fatty sulfonates, fatty sulfates, sulfonated benzimidazole derivatives and alkylarylsulfonates.

The compounds of formula (I) are distinguished inter alia also by excellent activity against fleas, not only adult fleas being rapidly killed but also, by a circuitous route, the juvenile stages of the fleas. Flea larvae hatching out from the flea eggs feed substantially on the excreta of the adult fleas. Since the compounds of formula (I) according to the invention kill the adult fleas very rapidly, the necessary excreta are absent and the juvenile stages are deprived of nutrient medium, so that they perish before reaching the adult stage.

The present invention therefore relates preferably to a method of controlling parasites on human beings, domestic animals, productive livestock and pets, wherein an effective amount of a composition comprising at least one compound of formula (I), or a physiologically tolerable salt thereof, is administered systemically or, preferably, topically to the warm- blooded animal.

The long-ter action is achieved by the compounds of formula (I) according to the invention with various forms of administration, for example by administering the active ingredient in a formulated form externally or internally to the animal to be treated."Formulated"in this case means, for example, in the form of a powder, a tablet or granules, in liposomes or a capsule, in the form of an mulsion, a foam or a spray, in microencapsulated form or in pour-on or spot-on form. It will be understood that all orally administrable compositions comprise, in addition to customary formulation substances, further additives that encourage the host animal to take the composition orally voluntarily, e. g. suitable odorants and flavourings.

Percutaneous administration, e. g. by subcutaneous or intramuscular injection or as a depot preparation in the form of an implant, and topical application, for example in pour-on or spot- on form, represent preferred subjects of this invention on account of their being easy to carry out. A further mode of administration is oral administration, e. g. in the form of a tablet.

Percutaneous and topical forms of administration are of particular interest and give excellent results.

Percutaneous forms of administration include, for example, subcutaneous, intramuscular and even intravenous administration of injectable forms. In addition to the customary syringes with needles, it is also possible to use needle-less high-pressure syringe devices.

Pour-on and spot-on formulations are especially preferred forms of topical administration, but administration in the form of sprays, ointments, solutions or powders may also be expedient.

By selection of a suitable formulation, it is possible to enhance the ability of the active ingre- dients to penetrate the living tissue of the host animal and/or to maintain their availability.

That is important when, for example, more sparingly soluble active ingredients are used, the low solubility of which requires means for enhancing solubility, since in such cases the animal's body fluid is capable of dissolving only small amounts of active ingredients at a time.

Furthermore, in order to obtain a strongly delayed release of active ingredient, a compound of formula (I) according to the invention may also be present in a matrix formulation which physically prevents the active ingredient from being released and excreted prematurely and maintains the bioavailability of the active ingredient. Such a matrix formulation is injected into the body, e. g. intramuscularly or subcutaneously, and remains there as a form of depot from which the active ingredient is released continuously. Such matrix formulations are known to the person skilled in the art. They are generally wax-like, semi-solid substances, for example vegetable waxes and polyethylene glycols having a high molecular weight, or solid polymer formulations, for example so-called microspheres.

The rate of release of the active ingredient from the implant and thus the period of time over which the implant exhibits an action is generally determined by the accuracy with which the implant has been calibrated (amount of active ingredient in the implant), the environment around the implant and the polymer formulation from which the implant has been made.

The administration of veterinary medicinal additives to animal feed is well known in the field of animal health. It is usual first to prepare a so-called premix in which the active ingredient is dispersed in a liquid or is in finely divided form in solid carriers. That premix can normally comprise about 1 to 800 mg of compound per kg of premix, depending on the desired final concentration in the feed.

Since the compounds of formula (I) according to the invention may be hydrolyse by the constituents of the feed, they should be formulated in a protective matrix, for example in gelatin, before being added to the premix.

The present invention accordingly relates also to the aspect of controlling parasites by administering to the host animal with its food a compound of formula (I) that has been protected against hydrolysis.

A compound of formula (I) according to the invention is advantageously administered in a dose of from 0.01 to 800 mg/kg, preferably from 0.1 to 200 mg/kg, especially from 0.5 to 30 mg/kg, body weight, based on the host animal.

A good dose that can be routinely administered to the host animal is from 0.5 to 100 mg/kg, especially from 0.1 to 40 mg/kg, body weight. The administration is effected at suitable intervals in dependence upon the mode of administration and body weight.

The total dose may vary from one species of animal to another and also within a species of animal for the same active ingredient, since it depends inter alia on the weight, age and constitution of the host animal.

When used according to the invention, the compound of formula (I) according to the inven- tion will normally be administered not in pure form but, preferably, in the form of a compo- sition that comprises, in addition to the active ingredient, constituents that assist administra- tion, suitable constituents being those which are tolerated by the host animal. It is of course possible, in addition to controlling the adult parasites in accordance with the invention, also to use conventional methods to control the juvenile stages of the fleas, although the latter is not absolutely essential.

Such compositions to be administered in accordance with the invention generally comprise from 0.1 to 99 % by weight, especially from 0.1 to 95 % by weight, of a compound of formula (I) according to the invention and from 99.9 to 1 % by weight, especially from 99.9 to 5 % by weight, of a solid or liquid, physiologically tolerable carrier, including from 0 to 25 % by weight, especially from 0.1 to 25 % by weight, of a non-toxic dispersant.

Whereas commercial products will preferably be formulated as concentrates, the end user will normally employ dilute formulations.

Such formulations may also comprise further auxiliaries, such as stabilisers, antifoams, viscosity regulators, binders and tackifiers as well as other active ingredients for obtaining special effects.

The physiologically tolerable carriers known from veterinary medicinal practice for oral, percutaneous and topical administration can be used as formulation auxiliaries. Some examples are given below.

Suitable carriers are especially fillers, such as sugars, e. g. lactose, saccharose, mannitol or sorbitol, cellulose preparations and/or calcium phosphates, for example tricalcium phosphate or calcium hydrogen phosphate, and binders, such as starch pastes using, for example, maize, wheat, rice or potato starch, gelatin, tragacanth, methylcellulose and/or, if desired, disintegrators, such as the above-mentioned starches, also carboxymethyl starch, cross- linked polyvinylpyrrolidone, agar, alginic acid or a salt thereof, such as sodium alginate.

Adjuvants are especially flow conditioners and lubricants, for example silicic acid, talc, stearic acid or salts thereof, such as magnesium or calcium stearate, and/or polyethylene glycol. Dragée cores can be provided with suitable, optionally enteric, coatings, there being used inter alia concentrated sugar solutions which may comprise gum arabic, talc, polyvinyl- pyrrolidone, polyethylene glycol and/or titanium dioxide, or coating solutions in suitable organic solvents or solvent mixtures, or, for the preparation of enteric coatings, solutions of suitable cellulose preparations, such as acetylcellulose phthalate or hydroxypropylmethyl- cellulose phthalate. Dyes, flavourings or pigments may be added to the tablets or dragée coatings, for example for identification purposes or to indicate different doses of active ingredient.

Other orally administrable preparations are hard gelatin capsules, and also soft sealed capsules made of gelatin and a plasticiser, such as glycerol or sorbitol. The hard gelatin capsules may comprise the active ingredient in the form of granules, for example in admixture with filles, such as lactose, binders, such as starches, and/or glidants, such as talc or magnesium stearate, and, if desired, stabilisers. In soft capsules, the active ingredient is preferably dissolved or suspended in suitable liquids, such as fatty oils, paraffin oil or liquid polyethylene glycols, to which stabilisers may likewise have been added. Preference is given inter alia to capsules that may either easily be bitten through or swallowed without being chewed.

The pour-on or spot-on method comprises applying the compound of formula (I) to a locally defined area of the skin or coat, advantageously on the back of the neck or the backbone of the animal. This is carried out, for example, by applying a swab or spray of the pour-on or spot-on formulation to a relatively small area of the coat from where the active ingredient becomes distributed over a wide area of the coat almost automatically as a result of the spreading constituents of the formulation assisted by the movements of the animal.

Pour-on and spot-on formulations advantageously comprise carriers that promote rapid distribution over the surface of the skin or in the coat of the host animal and are generally termed spreading oils. There are suitable, for example, oily solutions; alcoholic and iso- propanolic solutions, e. g. solutions of 2-octyl dodecanol or oleyl alcohol; solutions in esters of monocarboxylic acids, such as isopropyl myristate, isopropyl palmitate, lauric acid oxalic ester, oleic acid oleyl ester, oleic acid decyl ester, hexyl laurate, oleyl oleate, decyl oleate, capric acid esters of saturated fatty alcools of chain length C, 2-C, 8; solutions of esters of dicarboxylic acids, such as dibutyl phthalate, diisopropyl isophthalate, adipic acid diisopropyl ester, di-n-butyl adipate or solutions of esters of aliphatic acids, e. g. glycols. It may be advantageous for a dispersant known from the pharmaceutical or cosmetic industry also to be present. Examples are pyrrolidin-2-one, N-alkylpyrrolidin-2-one, acetone, polyethylene glycol and its ethers and esters, propylene glycol or synthetic triglycerides.

The oily solutions include e. g. vegetable oils, such as olive oil, groundnut oil, sesame oil, pine oil, linseed oit and castor oil. The vegetable oils may also be in epoxidised form. It is also possible to use paraffins and silicone oils.

Generally a pour-on or spot-on formulation will contain from 1 to 20 % by weight of a compound of formula (I), from 0.1 to 50 % by weight dispersant and from 45 to 98.9 % by weight solvent.

The pour-on or spot-on method can be used especially advantageously for herd animals, such as cattle, horses, sheep and pigs, where it is difficult or time-consuming to treat all the animals orally or via injection. By virtue of its simplicity, this method can of course also be used for all other animals, including individual domestic animals and pets, and is very popular with the keepers of the animals because it can often be carried out without the expert assistance of a veterinary surgeon.

Suitable for parenteral and percutaneous administration are oily injection solutions or suspensions, there being used suitable lipophilic solvents or vehicles, such as fatty oils, for example sesame oil, or synthetic fatty acid esters, for example ethyl oleate, or triglycerides, or aqueous injection solutions or suspensions that comprise viscosity-increasing substances, for example sodium carboxymethylcellulose, sorbitol and/or dextran, and, optionally, stabilisers.

The preparations of the present invention can be prepared in a manner known per se, for example by means of conventional mixing, granulating, confectioning, dissolving or lyophi- lising processes. For example, pharmaceutical preparations for oral administration can be obtained by combining the active ingredient with solid carriers, optionally granulating the resulting mixture, and processing the mixture or granules, if desired or necessary after the addition of suitable excipients, to form tablets or dragée cores.

The following Examples serve merely to illustrate the invention and do not limit the invention.

Preferred formulations have especially the following composition (throughout, percentages are by weight): Emulsifiable concentrates: active ingredient: 1 to 90 %, preferably 5 to 20 % surface-active agent: 1 to 30 %, preferably 10 to 20 % liquid carrier: 5 to 94 %, preferably 70 to 85 % Dusts : active ingredient: 0.1 to 10 %, preferably 0.1 to 1 % solid carrier: 99.9 to 90 %, preferably 99.9 to 99 % Suspension concentrates: active ingredient: 5 to 75 %, preferably 10 to 50 % water: 94 to 24 %, preferably 88 to 30 % surface-active agent: 1 to 40 %, preferably 2 to 30 % Wettable powders: active ingredient: 0.5 to 90 %, preferably 1 to 80 % surface-active agent: 0.5 to 20 %, preferably 1 to 15 % solid carrier: 5 to 95 %, preferably 15 to 90 % Granules: active ingredient: 0.5 to 30 %, preferably 3 to 15 % solid carrier: 99.5 to 70 %, preferably 97 to 85 % injection solution: active ingredient: 0.1 to 10 %, preferably 0.5 to 5 % non-ionic surfactant: 0.1 to 30 %, preferably 0.5 to 10 % mixture of ethanol and propylene glycol: 60 to 99 %, preferably 85 to 90 % Iniection suspension (aqueous or oi) y): active ingredient: 0.1 to 20 %, preferably 1 to 10 % non-ionic surfactant: 0.1 to 20 %, preferably 1 to 10 % water or vegetable oil: 60 to 99 %, preferably 85 to 95 % The compositions may also comprise further ingredients, such as stabilisers, e. g. vegetable oils or epoxidised vegetable oils (epoxidised coconut oil, rapeseed oil or soybean oil), anti- foams, e. g. silicone oil, preservatives, viscosity regulators, binders and tackifiers as well as fertilisers or other active ingredients for obtaining special effects.

The following Examples illustrate the invention described above but do not limit the scope thereof in any way. Temperatures are given in degrees Celsius. The symbol'h'stands for 'hour'.

1. Svnthesis Examples Example 1: 3- (4'-Chlorobhenvl-4-6- (2, 6-difluorophenvl)-1, 2-dihvdrof1, 2, 4,51tetrazine a) 6.1 g of 4-bromobenzoic acid ethyl ester and 1.84 g of tetrakis (triphenylphosphine)- palladium are stirred in 140 ml of dimethoxyethane at room temperature for 1 h. 140 ml of 2M sodium carbonate solution and 5.0 g of 4-chlorophenylboronic acid are then added.

After being stirred at room temperature for 17 h, the reaction mixture is poured into water and extracted with ethyl acetate; the organic phase is dried with sodium sulfate and concentrated and the crude product is purified by means of flash chromatography. In this way 4-chlorobiphenyl-4-carboxylic acid ethyl ester is obtained. b) 3.04 g of 2,6-difluorobenzoic acid hydrazide, 2.7 g of triethylamine and 0.11 g of 4-di- methylaminopyridine are introduced into 20 ml of methylene chloride at 5°C and, in the course of 20 min. at 5-10°C, 3.91 g of 4- (4'-chlorophenyl)-benzoyl chloride dissolved in 20 ml of methylene chloride are added dropwise thereto. After being stirred at room temperature for 24 h, the reaction mixture is diluted with methylene chloride and washed with water; the organic phase is dried and concentrated and the residue is recrystallised from ethanol. In this way 4'-chlorobiphenyl-4-carboxylic acid N'- (2, 6-difluorobenzoyl)-hydrazide having a melting point of 261-265°C is obtained. c) At 110°C, 6.97 g of phosphorus pentachloride are introduced into 30 ml of dichloro- benzene and, in the course of 15 min., 2.88 g of 4'-chlorobiphenyl-4-carboxylic acid N'-(2,6- difluorobenzoyl)-hydrazide are added in portions thereto. After then being stirred for 2.5 h, the reaction mixture is concentrated and the residue is suspended in methanol and filtered.

In this way N- [chloro- (4'-chlorobiphenyl-4-yl)-methylidene]-N'- [chloro- (2, 6-difluorophenyl)- methylidene]-hydrazine having a melting point of 149-161 OC is obtained in the form of an E/Z mixture. d) 2.2 g of N- [chloro- (4'-chlorobiphenyl-4-yl)-methylidene]-N'- [chloro- (2, 6-difluorophenyl)- methylidene]-hydrazine are added, in portions, at 15-20°C to 22 mi of hydrazine (0.5 molar) in THF and stirring is carried out at room temperature for 45 h. The reaction mixture is then poured into water and the precipitated crystals are filtered and washed with water. Recrystal- lisation from ethyl acetate yields the title compound having a melting point of 242-248°C.

Example 2: 3- (4'-Chlorobiphenvl-4-vl)-6- (2. 6-difluorophenvl)-f 1, 2. 4, 5ltetrazine At 40°C, 500 mg of 3- (4'-chlorobiphenyl-4-yl)-6- (2, 6-difluorophenyl)-1,2-dihydro [1,2,4,5]- tetrazine are introduced into 12 ml of acetic acid and 0.25 ml of water; 90 mg of sodium nitrite are added and stirring is carried out at room temperature for 5 h. After filtration, the crude product is suspended first in diethyl ether and then in ethyl acetate. In this way, the title compound having a melting point of 230-232°C is obtained.

Example 3 : 3- (4'-Trifluoromethvlbiphenvl-4-vl)-6- (2, 6-difluorophenvl)-f1, 2, 4, 51tetrazine At room temperature, 0.5 g of 3- (4-bromophenyl)-6- (2, 6-difluorophenyl)- [1,2,4,5] tetrazine, 0.3 g of 4-trifluoromethylphenylboronic acid and 0.44 g of caesium fluoride are placed in 11 mi of dimethoxyethane and 11 ml of methanol. After the addition of 19.3 mg of palladium acetate and 54.1 mg of tri-o-tolylphosphine, reaction reaction mixture stirred stirred 50°C for 3 h and is then poured into water and extracted with ethyl acetate; the organic phase is dried and concentrated. The residue is stirred with 20 mi of diethyl ether and filtered off. In this way, the title compound having a melting point of 251-252°C is obtained.

Analogously to the procedures described above it is also possible to prepare the substances listed in the following Tables 1 to 4. The melting point values are given in °C.

Table 1: Compounds of the formula No. X, X2 R, R2 Phys. data 1.1 F F H 4- (4-F-Ph) 1.2 F F H 4-(2-Ci-Ph) FH4-(4-Cl-Ph)242-248°1.3F FH4-(3-CF3-Ph)1.4F FH4-(4-CF3-Ph)1.5F FH4-(2-CH3-Ph)1.6F 1.7 F F H 4- (3-CH3-Ph) FH4-(4-CH3-Ph)1.8F FH4-(3-OCF3-Ph)1.9F FH4-(4-OCF3-Ph)1.10F 1.11 F F H 4- (4-t-butyl-Ph) 1.12 F F H 4-(2, 4-CI2-Ph) FH4-(3,5-Cl2-Ph)1.13F FH4-(2,4-F2-Ph)1.14F FH4-(3,5-F2-Ph)1.15F FH4-(2-CF3-Ph)1.16F FH4-(4-OCH3-Ph)1.17F FH4-(4-SCH3-Ph)1.18F FH4-(3-OCH3-Ph)1.19F FH4-(3-Cl-Ph)1.20F FH4-(3,4-Cl2-Ph)1.21F 1.22 F F H 4- (3-CI-4-F-Ph) 1.23 F Cl H 4- (4-F-Ph) No. X, X2 R, R2 Phys. data 1.24 F Cl H 4-(2-CI-Ph) ClH4-(4-Cl-Ph)1.25F 1.26 F Cl H 4- (3-CF3-Ph) 1.27 F Cl H 4- (4-CF3-Ph) 1.28 F Cl H 4-(2-CH3-Ph) ClH4-(3-CH3-Ph)1.29F 1.30 F Cl H 4- (4-CH3-Ph) ClH4-(3-OCF3-Ph)1.31F 1.32 F Cl H 4- (4-OCF3-Ph) 1.33 F Cl H 4- (4-t-butyl-Ph) ClH4-(2,4-Cl2-Ph)1.34F ClH4-(3,5-Cl2-Ph)1.35F ClH4-(2,4-F2-Ph)1.36F 1.37 F Cl H 4- (3,5-F2-Ph) ClH4-(2-CF3-Ph)1.38F ClH4-(4-OCH3-Ph)1.39F ClH4-(4-SCH3-Ph)1.40F ClH4-(3-OCH3-Ph)1.41F ClH4-(3-Cl-Ph)1.42F ClH4-(3,4-Cl2-Ph)1.43F ClH4-(3-Cl-4-F-Ph)1.44F ClH4-(4-F-Ph)1.45Cl ClH4-(2-Cl-Ph)1.46Cl ClH4-(4-Cl-Ph)1.47Cl ClH4-(3-CF3-Ph)1.48Cl ClH4-(4-CF3-Ph)1.49Cl ClH4-(2-CF3-Ph)1.50Cl ClH4-(3-CH3-Ph)1.51Cl ClH4-(4-CH3-Ph)1.52Cl ClH4-(3-OCF3-Ph)1.53Cl ClH4-(4-OCF3-Ph)1.54Cl ClH4-(4-t-butuyl-Ph)1.55Cl ClH4-(2,4-Cl2-Ph)1.56Cl No. X, X2 R, R2 Phys. data 1.57 CI Cl H 4- (3, 5-CI2-Ph) 1.58 Cl Cl H 4-(2,4-F2-Ph) 1.59 CI Cl H 4-(3,5-F2-Ph) 1.60 CI Cl H 4- (2-CF3-Ph) 1.61 CI Cl H 4- (4-OCH3-Ph) ClH4-(4-SCH3-Ph)1.62Cl ClH4-(3-OCH3-Ph)1.63Cl ClH4-(3-Cl-Ph)1.64Cl ClH4-(3-Cl2-Ph)1.65Cl ClH4-(3-Cl-4-F-Ph)1.66Cl FH3-(4-F-Ph)1.67F FH3-(2-Cl-Ph)1.68F FH3-(4-Cl-Ph)1.69F FH3-(3-CF3-Ph)1.70F FH3-(4-CF3-Ph)1.71F 1.72 F F H 3- (2-CH3-Ph) FH3-(3-CH3-Ph)1.73F FH3-(4-CH3-Ph)1.74F FH3-(3-OCF3-Ph)1.75F FH3-(4-OCF3-Ph)1.76F FH3-(4-t-butyl-Ph)1.77F FH3-(2,4-Cl2-Ph)1.78F FH3-(3,5-Cl2-Ph)1.79F FH3-(2,4-F2-Ph)1.80F FH3-(3,5-F2-Ph)1.81F FH3-(2-CF3-Ph)1.82F FH3-(4-OCH3-Ph)1.83F FH3-(4-SCH3-Ph)1.84F FH3-(3-OCH3-Ph)1.85F FH3-(3-Cl-Ph)1.86F FH3-(3,4-Cl2-Ph)1.87F FH3-(3-Cl-4-F-Ph)1.88F 1.89 F Cl H 3- (4-F-Ph) No. X1 X2 R1 R2 Phys. data 1.90 F Cl H 3-(2-CI-Ph) ClH3-(4-Cl-Ph)1.91F 1.92 F Cl H 3- (3-CF3-Ph) ClH3-(4-CF3-Ph)1.93F ClH3-(2-CH3-Ph)1.94F ClH3-(3-CH3-Ph)1.95F 1.96 F Cl H 3- (4-CH3-Ph) ClH3-(3-OCF3-Ph)1.97F ClH3-(4-OCF3-Ph)1.98F ClH3-(4-t-butyl-Ph)1.99F ClH3-(2,4-Cl2-Ph)1.100F 1.101 F Cl H 3- (3, 5-CI2-Ph) ClH3-(2,4-F2-Ph)1.102F 1.103 F Cl H 3- (3,5-F2-Ph) 1.104 F Cl H 3-(2-CF3-Ph) 1.105 F Cl H 3- (4-OCH3-Ph) ClH3-(4-SCH3-Ph)1.106F ClH3-(3-OCH3-Ph)1.107F ClH3-(3-Cl-Ph)1.108F 1.109 F Cl H 3- (3, 4-CI2-Ph) 1.110 F Cl H 3- (3-CI-4-F-Ph) ClH3-(4-F-Ph)1.111Cl ClH3-(2-Cl-Ph)1.112Cl ClH3-(4-Cl-Ph)1.113Cl ClH3-(3-CF3-Ph)1.114Cl ClH3-(4-CF3-Ph)1.115Cl 1.116 Cl Cl H 3-(2-CH3-Ph) ClH3-(3-CH3-Ph)1.117Cl ClH3-(4-CH3-Ph)1.118Cl ClH3-(3-OCF3-Ph)1.119Cl ClH3-(4-OCF3-Ph)1.120Cl 1.121 Cl Cl H 3- (4-t-butyl-Ph) ClH3-(2,4-Cl2-Ph)1.122Cl No. X, X2 R, R2 Phys. data 1.123 Cl Cl H 3- (3, 5-CI2-Ph) 1.124 Cl Cl H 3-(2, 4-F2-Ph) 1.125 Cl Cl H 3- (3, 5-F2-Ph) ClH3-(2-CF3-Ph)1.126Cl 1.127 Cl Cl H 3- (4-OCH3-Ph) 1.128 Cl Cl H 3- (4-SCH3-Ph) 1.129 Cl Cl H 3- (3-OCH3-Ph) ClH3-(3-Cl-Ph)1.130Cl 1.131 Cl Cl H 3-(3, 4-CI2-Ph) 1.132 Cl Cl H 3- (3-CI-4-F-Ph) F2-CH34-(4-F-Ph)1.133F F2-CH34-(2-Cl-Ph)1.134F F2-CH34-(4-Cl-Ph)1.135F F2-CH34-(3-CF3-Ph)1.136F F2-CH34-(4-CF3-Ph)1.137F F2-CH34-(2-CH3-Ph)1.138F F2-CH34-(3-CH3-Ph)1.139F F2-CH34-(4-CH3-Ph)1.140F F2-CH34-(3-OCF3-Ph)1.141F F2-CH34-(4-OCF3-Ph)1.142F F2-CH34-(4-t-butyl-Ph)1.143F F2-CH34-(2,4-Cl2-Ph)1.144F F2-CH34-(3,5-Cl3-Ph)1.145F F2-CH34-(2.4-F2-Ph)1.146F F2-CH34-(3,5-F2-Ph)1.147F F2-CH34-(2-CF3-Ph)1.148F F2-CH34-(4-OCH3-Ph)1.149F F2-CH34-(4-SCH3-Ph)1.150F F2-CH34-(3-OCH3-Ph)1.151F F2-CH34-(3-Cl-Ph)1.152F 1.1532-CH34-(3,4-Cl2-Ph)F F2-CH34-(3-Cl-4-F-Ph)1.154F 1.155 F Cl 2-CH3 4-(4-F-Ph) No. X, X2 R, R2 Phys. data 1.156 F Cl 2-CH3 4-(2-CI-Ph) 1.157 F Cl 2-CH3 4-(4-CI-Ph) Cl2-CH34-(3-CF3-Ph)1.158F Cl2-CH34-(4-CF3-Ph)1.159F 1.160 F Cl 2-CH3 4-(2-CH3-Ph) Cl2-CH34-(3-CH3-Ph)1.161F Cl2-CH34-(4-CH3-Ph)1.162F Cl2-CH34-(3-OCF3-Ph)1.163F Cl2-CH34-(4-OCF3-Ph)1.164F Cl2-CH34-(4-t-butyl-Ph)1.165F 1.166 F Cl 2-CH3 4-(2, 4-CI2-Ph) Cl2-CH34-(3,5-CL2-Ph)1.167F 1.168 F Cl 2-CH3 4-(2, 4-F2-Ph) Cl2-CH34-(3,5-F2-Ph)1.169F 1.170 F Cl 2-CH3 4-(2-CF3-Ph) Cl2-CH34-(4-OCH3-Ph)1.171F Cl2-CH34-(4-SCH3-Ph)1.172F Cl2-CH34-(3-OCH3-Ph)1.173F Cl2-CH34-(3-Cl-Ph)1.174F Cl2-CH34-(3,4-Cl2-Ph)1.175F Cl2-CH34-(3-Cl-4-F-Ph)1.176F Cl2-CH34-(4-F-Ph)1.177Cl 1.178 Cl Cl 2-CH3 4-(2-CI-Ph) Cl2-CH34-(4-Cl-Ph)1.179Cl Cl2-CH34-(3-CF3-Ph)1.180Cl Cl2-CH34-(4-CF3-Ph)1.181Cl 1.182 Cl Cl 2-CH3 4-(2-CH3-Ph) Cl2-CH34-(3-CH3-Ph)1.183Cl Cl2-CH34-(4-CH3-Ph)1.184Cl Cl2-CH34-(3-OCF3-Ph)1.185Cl Cl2-CH34-(4-OCF3-Ph)1.186Cl Cl2-CH34-(4-t-butyl-Ph)1.187Cl Cl2-CH34-(2,4-Cl2-Ph)1.188Cl No. X, X2 R, R2 Phys. data 1.189 Cl Cl 2-CH3 4- (3, 5-CI2-Ph) Cl2-CH34-(2,4-F2-Ph)1.190Cl Cl2-CH34-(3,5-F2-Ph)1.191Cl 1.192 Cl Cl 2-CH3 4-(2-CF3-Ph) Cl2-CH34-(4-OCH3-Ph)1.193Cl Cl2-CH34-(4-SCH3-Ph)1.194Cl 1.195 Cl Cl 2-CH3 4-(3-OCH3-Ph) Cl2-CH34-(3-Cl-Ph)1.196Cl 1.197 Cl Cl 2-CH3 4-(3, 4-CI2-Ph) Cl2-CH34-(3-Cl-4-F-Ph)1.198Cl F2-CH33-(4-F-Ph)1.199F F2-CH33-(2-Cl-Ph)1.200F F2-CH33-(4-Cl-Ph)1.201F F2-CH33-(3-CF3-Ph)1.202F F2-CH33-(4-CF3-Ph)1.203F F2-CH33-(2-CH3-Ph)1.204F F2-CH33-(3-CH3-Ph)1.205F F2-CH33-(4-CH3-Ph)1.206F F2-CH33-(3-OCF3-Ph)1.207F F2-CH33-(4-OCF3-Ph)1.208F F2-CH33-(4-t-butyl-Ph)1.209F F2-CH33-(2,4-Cl2-Ph)1.210F F2-CH33-(3,5-Cl2-Ph)1.211F F2-CH33-(2,4-F2-Ph)1.212F F2-CH33-(3,5-F2-Ph)1.213F F2-CH33-(2-CF3-Ph)1.214F F2-CH33-(4-OCH3-Ph)1.215F F2-CH33-(4-SCH3-Ph)1.216F F2-CH33-(3-OCH3-Ph)1.217F F2-CH33-(3-Cl-Ph)1.218F F2-CH33-(3,4-Cl2-Ph)1.219F F2-CH33-(3-Cl-4-F-Ph)1.220F 1.221 F Cl 2-CH3 3-(4-F-Ph) No. X, X2 R, R2 Phys. data 1.222 F Cl 2-CH3 3-(2-CI-Ph) Cl2-CH33-(4-Cl-Ph)1.223F Cl2-CH33-(3-CF3-Ph)1.224F Cl2-CH33-(4-CF3-Ph)1.225F 1.226 F Cl 2-CH3 3-(2-CH3-Ph) Cl2-CH33-(3-CH3-Ph)1.227F Cl2-CH33-(4-CH3-Ph)1.228F Cl2-CH33-(3-OCF3-Ph)1.229F Cl2-CH33-(4-OCF3-Ph)1.230F Cl2-CH33-(4-t-butyl-Ph)1.231F 1.232 F Cl 2-CH3 3-(2, 4-CI2-Ph) Cl2-CH33-(3,5-Cl2-Ph)1.233F 1.234 F Cl 2-CH3 3-(2, 4-F2-Ph) Cl2-CH33-(3,5-F2-Ph)1.235F 1.236 F Cl 2-CH3 3-(2-CF3-Ph) Cl2-CH33-(4-OCH3-Ph)1.237F Cl2-CH33-(4-SCH3-Ph)1.238F Cl2-CH33-(3-OCH3-Ph)1.239F Cl2-CH33-(3-Cl-Ph)1.240F Cl2-CH33-(3,4-Cl2-Ph)1.241F Cl2-CH33-(3-Cl-4-F-Ph)1.242F Cl2-CH33-(4-F-Ph)1.243Cl 1.244 Cl Cl 2-CH3 3-(2-CI-Ph) Cl2-CH33-(4-Cl-Ph)1.245Cl Cl2-CH33-(3-CF3-Ph)1.246Cl Cl2-CH33-(4-CF3-Ph)1.247Cl 1.248 Cl Cl 2-CH3 3-(2-CH3-Ph) Cl2-CH33-(3-CH3-Ph)1.249Cl Cl2-CH33-(4-CH3-Ph)1.250Cl Cl2-CH33-(3-OCF3-Ph)1.251Cl Cl2-CH33-(4-OCF3-Ph)1.252Cl Cl2-CH33-(4-t-butyl-Ph)1.253Cl 1.254 Cl Cl 2-CH3 3-(2, 4-CI2-Ph) No. X, X2 R, R2 Phys. data 1.255 Cl Cl 2-CH3 3-(3, 5-CI2-Ph) 1.256 Cl Cl 2-CH3 3-(2,4-F2-Ph) Cl2-CH33-(3,5-F2-Ph)1.257Cl 1.258 Cl Cl 2-CH3 3-(2-CF3-Ph) Cl2-CH33-(4-OCH3-Ph)1.259Cl 1.260 Cl Cl 2-CH3 3-(4-SCH3-Ph) Cl2-CH33-(3-OCH3-Ph)1.261Cl 1.262 Cl Cl 2-CH3 3-(3-CI-Ph) Cl2-CH33-(3,4-Cl2-Ph)1.263Cl Cl2-CH33-(3-Cl-4-F-Ph)1.264Cl F2-Cl4-(4-F-Ph)1.265F F2-Cl4-(2-Cl-Ph)1.266F F2-Cl4-(4-Cl-Ph)1.267F F2-Cl4-(3-CF3-Ph)1.268F F2-Cl4-(4-CF3-Ph)1.269F F2-Cl4-(2-CH3-Ph)1.270F F2-Cl4-(3-CH3-Ph)1.271F F2-Cl4-(4-CH3-Ph)1.272F F2-Cl4-(3-OCF3-Ph)1.273F F2-Cl4-(4-OCF3-Ph)1.274F F2-Cl4-(4-t-butyl-Ph)1.275F F2-Cl4-(2,4-Cl2-Ph)1.276F F2-Cl4-(3,5-Cl2-Ph)1.277F F2-Cl4-(2,4-F2-Ph)1.278F F2-Cl4-(3,5-F2-Ph)1.279F F2-Cl4-(2-CF3-Ph)1.280F 1281 F F 2-CI 4- (4-OCH3-Ph) F2-Cl4-(4-SCH3-Ph)1.282F F2-Cl4-(3-OCH3-Ph)1.283F F2-Cl4-(3-Cl-Ph)1.284F F2-Cl4-(3,4-Cl2-Ph)1.285F F2-Cl4-(3-Cl-4-F-Ph)1.286F F2-Cl4-(4-F-Ph)1.287F No. X, X2 R, R2 Phys. data 1.288 F Cl 2-CI 4-(2-CI-Ph) Cl2-Cl4-(4-Cl-Ph)1.289F Cl2-Cl4-(3-CF3-Ph)1.290F Cl2-Cl4-(4-CF3-Ph)1.291F 1.292 F Cl 2-CI 4-(2-CH3-Ph) Cl2-Cl4-(3-CH3-Ph)1.293F Cl2-Cl4-(4-CH3-Ph)1.294F Cl2-Cl4-(3-OCF3-Ph)1.295F Cl2-Cl4-(4-OCF3-Ph)1.296F 1.297 F Cl 2-CI 4-(4-t-butyl-Ph) 1.298 F Cl 2-CI 4-(2, 4-CI2-Ph) 1.299 F Cl 2-CI 4-(3, 5-CI2-Ph) 1.300 F Cl 2-CI 4-(2, 4-F2-Ph) Cl2-Cl4-(3,5-F2-Ph)1.301F 1.302 F Cl 2-CI 4-(2-CF3-Ph) Cl2-Cl4-(4-OCH3Ph)1.303F Cl2-Cl4-(4-SCH3-Ph)1.304F Cl2-Cl4-(3-OCH3-Ph)1.305F Cl2-Cl4-(3-Cl-Ph)1.306F Cl2-Cl4-(3,4-Cl2-Ph)1.307F Cl2-Cl4-(3-Cl-4-F-Ph)1.308F Cl2-Cl4-(4-F-Ph)1.309F 1.310 Cl Cl 2-CI 4-(2-CI-Ph) Cl2-Cl4-(4-Cl-Ph))1.311Cl 1.3122-Cl4-(3-CF3-Ph)Cl Cl2-Cl4-(4-CF3-Ph)1.313Cl 1.314 Cl Cl 2-CI 4-(2-CH3-Ph) Cl2-Cl4-(3-CH3-Ph)1.315Cl 1.3162-Cl4-(4-CH3-Ph)Cl Cl2-Cl4-(3-OCF3-Ph)1.317Cl Cl2-Cl4-(4-OCF3-Ph)1.318Cl Cl2-Cl4-(4-t-butyl-Ph)1.319Cl Cl2-Cl4-(2,4-Cl2-Ph)1.320Cl No. X, X2 R, R2 Phys. data Cl2-Cl4-(3,5-Cl2-Ph)1.321Cl 1.322 Cl Cl 2-CI 4-(2, 4-F2-Ph) 1.323 Cl Cl 2-CI 4-(3,5-F2-Ph) 1.324 Cl Cl 2-CI 4-(2-CF3-Ph) 1.325 Cl Cl 2-Cl 4- (4-OCH3-Ph) 1.326 Cl Cl 2-CI 4- (4-SCH3-Ph) Cl2-Cl4-(3-OCH3-Ph)1.327Cl 1.328 Cl Cl 2-Ci 4- (3-CI-Ph) Cl2-Cl4-(3,4-Cl2-Ph)1.329Cl Cl2-Cl4-(3-Cl-4-F-Ph)1.330Cl F2-Cl3-(4-F-Ph)1.331F 1.332 F F 2-CI 3-(2-CI-Ph) F2-Cl3-(4-Cl-Ph)1.333F F2-Cl3-(3-CF3-Ph)1.334F F2-Cl3-(4-CF3-Ph)1.335F F2-Cl3-(2-CH3-Ph)1.336F F2-Cl3-(3-CH3-Ph)1.337F F2-Cl3-(4-CH3-Ph)1.338F F2-Cl3-(3-OCF3-Ph)1.339F F2-Cl3-(4-OCF3-Ph)1.340F F2-Cl3-(4-t-butyl-Ph)1.341F F2-Cl3-(2,4-Cl2-Ph)1.342F F2-Cl3-(3,5-Cl2-Ph)1.343F F2-Cl3-(2,4-F2-Ph)1.344F F2-Cl3-(3,5-F2-Ph)1.345F F2-Cl3-(2-CF3-Ph)1.346F F2-Cl3-(4-OCH3-Ph)1.347F F2-Cl3-(4-SCH3-Ph)1.348F F2-Cl3-(3-OCH3-Ph)1.349F F2-Cl3-(3-Cl-Ph)1.350F F2-Cl3-(3,4-Cl2-Ph)1.351F F2-Cl3-(3-Cl-4-F-Ph)1.352F 1.353 F Cl 2-CI 3-(4-F-Ph) No. X, X2 R, R2 Phys. data 1.354 F Cl 2-CI 3-(2-CI-Ph) Cl2-Cl3-(4-Cl-Ph)1.355F Cl2-Cl3-(3-CF3-Ph)1.356F Cl2-Cl3-(4-CF3-Ph)1.357F 1.358 F Cl 2-CI 3-(2-CH3-Ph) Cl2-Cl3-(3-CH3-Ph)1.359F Cl2-Cl3-(4-CH3-Ph)1.360F Cl2-Cl3-(3-OCF3-Ph)1.361F Cl2-Cl3-(4-OCF3-Ph)1.362F Cl2-Cl3-(4-t-butyl-Ph)1.363F 1.364 F Cl 2-CI 3-(2, 4-CI2-Ph) Cl2-Cl3-(3,5-Cl2-Ph)1.365F 1.366 F Cl 2-CI 3-(2, 4-F2-Ph) Cl2-Cl3-(3,5-F2-Ph)1.367F 1.368 F Cl 2-CI 3-(2-CF3-Ph) Cl2-Cl3-(4-OCH3-Ph)1.369F Cl2-Cl3-(4-SCH3-Ph)1.370F Cl2-Cl3-(3-OCH3-Ph)1.371F Cl2-Cl3-(3-Cl-Ph)1.372F Cl2-Cl3-(3,4-Cl2-Ph)1.373F Cl2-Cl3-(3-Cl-4-F-Ph)1.374F 1.375 Cl Cl 2-CI 3- (4-F-Ph) 1.376 Cl Cl 2-CI 3-(2-CI-Ph) Cl2-Cl3-(4-Cl-Ph)1.377Cl Cl2-Cl3-(3-CF3-Ph)1.378Cl Cl2-Cl3-(4-CF3-Ph)1.379Cl 1.380 Cl Cl 2-CI 3-(2-CH3-Ph) Cl2-Cl3-(3-CH3-Ph)1.381Cl Cl2-Cl3-(4-CH3-Ph)1.382Cl Cl2-Cl3-(3-OCF3-Ph)1.383Cl Cl2-Cl3-(4-OCF3-Ph)1.384Cl Cl2-Cl3-(4-t-butyl-Ph)1.385Cl 1.386 Cl Cl 2-CI 3-(2, 4-CI2-Ph) No. X, X2 R, R2 Phys. data 1.387 Cl Cl 2-CI 3-(3, 5-CI2-Ph) 1.388 Cl Cl 2-CI 3-(2, 4-F2-Ph) Cl2-Cl3-(3,5-F2-Ph)1.389Cl 1.390 Cl Cl 2-CI 3-(2-CF3-Ph) 1.391 Cl Cl 2-CI 3-(4-OCH3-Ph) Cl2-Cl3-(4-SCH3-Ph)1.392Cl Cl2-Cl3-(3-OCH3-Ph)1.393Cl Cl2-Cl3-(3-Cl-Ph)1.394Cl Cl2-Cl3-(3,4-Cl2-Ph)1.395Cl 1.396 Cl Cl 2-CI 3-(3-Ci-4-F-Ph) F2-OCH34-(4-F-Ph)1.397F Cl2-Cl4-(2-Cl-Ph)1.398Cl F2-OCH34-(4-Cl-Ph)1.399F F2-OCH34-(3-CF3-Ph)1.400F F2-OCH34-(4-CF3-Ph)1.401F F2-OCH34-(2-CH3-Ph)1.402F F2-OCH34-(3-CH3-Ph)1.403F F2-OCH34-(4-CH3-Ph)1.404F F2-OCH34-(3-OCF3-Ph)1.405F F2-OCH34-(4-OCF3-Ph)1.406F F2-OCH34-(4-t-butyl-Ph)1.407F F2-OCH34-(2,4-Cl2-Ph)1.408F F2-OCH34-(3,5-Cl2-Ph)1.409F F2-OCH34-(2,4-F2-Ph)1.410F F2-OCH34-(3,5-F2-Ph)1.411F F2-OCH34-(2-CF3-Ph)1.412F F2-OCH34-(4-OCH3-Ph)1.413F F2-OCH34-(4-SCH3-Ph)1.414F F2-OCH34-(3-OCH3-Ph)1.415F F2-OCH34-(3-Cl-Ph)1.416F F2-OCH34-(3,4-Cl2-Ph)1.417F F2-OCH34-(3-Cl-4-F-Ph)1.418F 1.419 F Cl 2-OCH3 4-(4-F-Ph) No. X, X2 R, R2 Phys. data 1.420 F Cl 2-OCH3 4-(2-CI-Ph) Cl2-OCH34-(4-Cl-Ph)1.421F Cl2-OCH34-(3-CF3-Ph)1.422F Cl2-OCH34-(4-CF3-Ph)1.423F 1.424 F Cl 2-OCH3 4-(2-CH3-Ph) Cl2-OCH34-(3-CH3-Ph)1.425F Cl2-OCH34-(4-CH3-Ph)1.426F Cl2-OCH34-(3-OCF3-Ph)1.427F Cl2-OCH34-(4-OCF3-Ph)1.428F Cl2-OCH34-(4-t-butyl-Ph)1.429F 1.430 F Cl 2-OCH3 4-(2, 4-CI2-Ph) Cl2-OCH34-(3,5-Cl2-Ph)1.431F 1.432 F Cl 2-OCH3 4-(2,4-F2-Ph) Cl2-OCH34-(3,5-F2-Ph)1.433F Cl2-OCH34-(2-CF3-Ph)1.434F Cl2-OCH34-(4-OCH3-Ph)1.435F Cl2-OCH34-(4-SCH3-Ph)1.436F Cl2-OCH34-(3-OCH3-Ph)1.437F 1.438 F Cl 2-OCH3 4-(3-CI-Ph) Cl2-OCH34-(3,4-Cl2-Ph)1.439F Cl2-OCH34-(3-Cl-4-F-Ph)1.440F Cl2-OCH34-(4-F-Ph)1.441Cl 1.442 Cl Cl 2-OCH3 4-(2-CI-Ph) Cl2-OCH34-(4-Cl-Ph)1.443Cl Cl2-OCH34-(3-CF3-Ph)1.444Cl Cl2-OCH34-(4-CF3-Ph)1.445Cl 1.446 Cl Cl 2-OCH3 4-(2-CH3-Ph) Cl2-OCH34-(3-CH3-Ph)1.447Cl Cl2-OCH34-(4-CH3-Ph)1.448Cl Cl2-OCH34-(3-OCF3-Ph)1.449Cl Cl2-OCH34-(4-OCF3-Ph)1.450Cl Cl2-OCH34-(4-t-butyl-Ph)1.451Cl 1.452 Cl Cl 2-OCH3 4-(2, 4-CI2-Ph) No. X, X2 R, R2 Phys. data 1.453 Cl Cl 2-OCH3 4-(3, 5-CI2-Ph) 1.454 Cl Cl 2-OCH3 4-(2,4-F2-Ph) 1.455 Cl Cl 2-OCH3 4-(3, 5-F2-Ph) Cl2-OCH34-(2-CF3-Ph)1.456Cl 1.457 Cl Cl 2-OCH3 4-(4-OCH3-Ph) Cl2-OCH34-(4-SCH3-Ph)1.458Cl Cl2-OCH34-(3-OCH3-Ph)1.459Cl 1.460 Cl Cl 2-OCH3 4-(3-CI-Ph) Cl2-OCH34-(3,4-Cl2-Ph)1.461Cl Cl2-OCH34-(3-Cl-4-F-Ph)1.462Cl F2-OCH33-(4-F-Ph)1.463F F2-OCH33-(2-Cl-Ph)1.464F F2-OCH33-(4-Cl-Ph)1.465F F2-OCH33-(3-CF3-Ph)1.466F F2-OCH33-(4-CF3-Ph)1.467F F2-OCH33-(2-CH3-Ph)1.468F F2-OCH33-(3-CH3-Ph)1.469F F2-OCH33-(4-CH3-Ph)1.470F F2-OCH33-(3-OCF3-Ph)1.471F F2-OCH33-(4-OCF3-Ph)1.472F F2-OCH33-(4-t-butyl-Ph)1.473F F2-OCH33-(2,4-Cl2-Ph)1.474F F2-OCH33-(3,5-Cl2-Ph)1.475F F2-OCH33-(2,4-F2-Ph)1.476F F2-OCH33-(3,5-F2-Ph)1.477F F2-OCH33-(2-CF3-Ph)1.478F F2-OCH33-(4-OCH3-Ph)1.479F F2-OCH33-(4-SCH3-Ph)1.480F F2-OCH33-(3-OCH3-Ph)1.481F F2-OCH33-(3-Cl-Ph)1.482F F2-OCH33-(3,4-Cl2-Ph)1.483F F2-OCH33-(3-Cl-4-F-Ph)1.484F F2-OCH33-(4-F-Ph)1.485F No. X, X2 R, R2 Phys. data 1.486 F Cl 2-OCH3 3-(2-CI-Ph) Cl2-OCH33-(4-Cl-Ph)1.487F Cl2-OCH33-(3-CF3-Ph)1.488F Cl2-OCH33-(4-CF3-Ph)1.489F 1.490 F Cl 2-OCH3 3-(2-CH3-Ph) Cl2-OCH33-(3-CH3-Ph)1.491F Cl2-OCH33-(4-CH3-Ph)1.492F Cl2-OCH33-(3-OCF3-Ph)1.493F Cl2-OCH33-(4-OCF3-Ph)1.494F Cl2-OCH33-(4-t-butyl-Ph)1.495F 1.496 F Cl 2-OCH3 3-(2, 4-CI2-Ph) Cl2-OCH33-(3,5-Cl2-Ph)1.497F 1.498 F Cl 2-OCH3 3-(2, 4-F2-Ph) Cl2-OCH33-(3,5-F2-Ph)1.499F 1.500 F Cl 2-OCH3 3-(2-CF3-Ph) Cl2-OCH33-(4-OCH3-Ph)1.501F Cl2-OCH33-(4-SCH3-Ph)1.502F Cl2-OCH33-(3-OCH3-Ph)1.503F Cl2-OCH33-(3-Cl-Ph)1.504F Cl2-OCH33-(3,4-Cl2-Ph)1.505F Cl2-OCH33-(3-Cl-4-F-Ph)1.506F Cl2-OCH33-(4-F-Ph)1.507F 1.508 Cl Cl 2-OCH3 3-(2-CI-Ph) Cl2-OCH33-(4-Cl-Ph)1.509Cl Cl2-OCH33-(3-CF3-Ph)1.510Cl Cl2-OCH33-(4-CF3-Ph)1.511Cl 1.512 Cl Cl 2-OCH3 3-(2-CH3-Ph) Cl2-OCH33-(3-CH3-Ph)1.513Cl Cl2-OCH33-(4-CH3-Ph)1.514Cl Cl2-OCH33-(3-OCF3-Ph)1.515Cl Cl2-OCH33-(4-OCF3-Ph)1.516Cl Cl2-OCH33-(4-t-butyl-Ph)1.517Cl 1.518 Cl Cl 2-OCH3 3-(2, 4-CI2-Ph) No. X, X2 R, R2 Phys. data Cl2-OCH33-(3,5-Cl2-Ph)1.519Cl 1.520 Cl Cl 2-OCH3 3-(2, 4-F2-Ph) Cl2-OCH33-(3,5-F2-Ph)1.521Cl 1.522 Cl Cl 2-OCH3 3-(2-CF3-Ph) 1.523 Cl Cl 2-OCH3 3-(4-OCH3-Ph) 1.524 Cl Cl 2-OCH3 3-(4-SCH3-Ph) Cl2-OCH33-(3-OCH3-Ph)1.525Cl 1.526 Cl Cl 2-OCH3 3-(3-CI-Ph) Cl2-OCH33-(3,4-Cl2-Ph)1.527Cl Cl2-OCH33-(3-Cl-4-F-Ph)1.528Cl F2-CF34-(4-F-Ph)1.529F F2-CF34-(2-Cl-Ph)1.530F F2-CF34-(4-Cl-Ph)1.531F F2-CF34-(3-CF3-Ph)1.532F F2-CF34-(4-CF3-Ph)1.533F F2-CF34-(2-CH3-Ph)1.534F F2-CF34-(3-CH3-Ph)1.535F F2-CF34-(4-CH3-Ph)1.536F F2-CF34-(3-OCF3-Ph)1.537F F2-CF34-(4-OCF3-Ph)1.538F F2-CF34-(4-t-butyl-Ph)1.539F F2-CF34-(2,4-Cl2-Ph)1.540F F2-CF34-(3,5-Cl2-Ph)1.541F 1.542FF2-CF34- (2, 4-F2-Ph) F2-CF34-(3,5-F2-Ph)1.543F F2-CF34-(2-CF3-Ph)1.544F F2-CF34-(4-OCH3-Ph)1.545F F2-CF34-(4-SCH3-Ph)1.546F F2-CF34-(3-OCH3-Ph)1.547F F2-CF34-(3-Cl-Ph)1.548F F2-CF34-(3,4-Cl2-Ph)1.549F F2-CF34-(3-Cl-4-F-Ph)1.550F Cl2-CF34-(4-F-Ph)1.551F No. X, X2 R, R2 Phys. data 1.552 F Cl 2-CF3 4-(2-CI-Ph) Cl2-CF34-(4-Cl-Ph)1.553F Cl2-CF34-(3-CF3-Ph)1.554F Cl2-CF34-(4-CF3-Ph)1.555F 1.556 F Cl 2-CF3 4-(2-CH3-Ph) Cl2-CF34-(3-CH3-Ph)1.557F Cl2-CF34-(4-CH3-Ph)1.558F Cl2-CF34-(3-OCF3-Ph)1.559F Cl2-CF34-94-OCF3-Ph)1.560F Cl2-CF34-(4-t-butyl-Ph)1.561F 1.562 F Cl 2-CF3 4-(2, 4-CI2-Ph) Cl2-CF34-(3,5-Cl2-Ph)1.563F 1.564 F Cl 2-CF3 4-(2, 4-F2-Ph) Cl2-CF34-(3,5-F2-Ph)1.565F 1.566 F Cl 2-CF3 4-(2-CF3-Ph) Cl2-CF34-(4-OCH3-Ph)1.567F Cl2-CF34-(4-SCH3-Ph)1.568F Cl2-CF34-(3-OCH3-Ph)1.569F Cl2-CF34-(3-Cl-Ph)1.570F Cl2-CF34-(3,4-Cl2-Ph)1.571F Cl2-CF34-(3-Cl-4-F-Ph)1.572F Cl2-CF34-(4-F-Ph)1.573Cl 1.574 Cl Cl 2-CF3 4-(2-CI-Ph) Cl2-CF34-(4-Cl-Ph)1,575Cl Cl2-CF34-(3-CF3-Ph)1.576Cl Cl2-CF34-(4-CF3-Ph)1.577Cl 1.578 Cl Cl 2-CF3 4-(2-CH3-Ph) Cl2-CF34-(3-CH3-Ph)1.579Cl Cl2-CF34-(4-CH3-Ph)1.580Cl Cl2-CF34-(3-OCF3-Ph)1.581Cl Cl2-CF34-(4-OCF3-Ph)1.582Cl Cl2-CF34-(4-t-butyl-Ph)1.583Cl Cl2-CF34-(2,4-Cl2-Ph)1.584Cl No. X, X2 R, R2 Phys. data 1.585 Cl Cl 2-CF3 4- (3, 5-CI2-Ph) 1.586 Cl Cl 2-CF3 4-(2,4-F2-Ph) 1.587 Cl Cl 2-CF3 4-(3, 5-F2-Ph) 1.588 Cl Cl 2-CF3 4-(2-CF3-Ph) Cl2-CF34-(4-OCH3-Ph)1.589Cl 1.590 CI Cl 2-CF3 4- (4-SCH3-Ph) Cl2-CF34-(3-OCH3-Ph)1.591Cl 1.592 Cl Cl 2-CF3 4-(3-CI-Ph) Cl2-CF34-(3,4-Cl2-Ph)1.593Cl Cl2-CF34-(3-Cl-4-F-Ph)1.594Cl F2-CF33-(4-F-Ph)1.595F F2-CF33-(2-Cl-Ph)1.596F F2-CF33-(4-Cl-Ph)1.597F F2-CF33-(3-CF3-Ph)1.598F F2-CF33-(4-CF3-Ph)1.599F F2-CF33-(2-CH3-Ph)1.600F F2-CF33-(3-CH3-Ph)1.601F F2-CF33-(4-CH3-Ph)1.602F F2-CF33-(3-OCF-Ph)1.603F F2-CF33-(4-OCF-Ph)1.604F F2-CF33-(4-t-butyl-Ph)1.605F F2-CF33-(2,4-Cl2-Ph)1.606F F2-CF33-(3,5-Cl2-Ph)1.607F F2-CF33-(2,4-F2-Ph)1.608F 1. 609 F F 2-CF3 3- (3,5-F2-Ph) F2-CF33-(2-CF3-Ph)1.610F F2-CF33-(4-OCH3-Ph)1.611F F2-CF33-(4-SCH3-Ph)1.612F F2-CF33-(3-OCH3-Ph)1.613F F2-CF33-(3-Cl-Ph)1.614F F2-CF33-(3,4-Cl2-Ph)1.615F F2-CF33-(3-Cl-4-F-Ph)1.616F F2-CF33-(4-F-Ph)1.617F No. X, X2 R, R2 Phys. data 1.618 F Cl 2-CF3 3-(2-CI-Ph) 1.619 F Cl 2-CF3 3-(4-CI-Ph) Cl2-CF33-(3-CF3-Ph)1.620F Cl2-CF33-(4-CF3-Ph)1.621F 1.622 F Cl 2-CF3 3-(2-CH3-Ph) Cl2-CF33-(3-CH3-Ph)1.623F Cl2-CF33-(4-CH3-Ph)1.624F Cl2-CF33-(3-OCF3-Ph)1.625F Cl2-CF33-(4-OCF3-Ph)1.626F Cl2-CF33-(4-t-butyl-Ph)1.627F 1.628 F Cl 2-CF3 3-(2, 4-CI2-Ph) Cl2-CF33-(3,5-Cl2-Ph)1.629F 1.630 F Cl 2-CF3 3-(2, 4-F2-Ph) Cl2-CF33-(3,5-F2-Ph)1.631F 1.632 F Cl 2-CF3 3-(2-CF3-Ph) Cl2-CF33-(4-OCH3-Ph)1.633F Cl2-CF33-(4-SCH3-Ph)1.634F Cl2-CF33-(3-OCH3-Ph)1.635F Cl2-CF33-(3-Cl-Ph)1.636F Cl2-CF33-(3,4-Cl2-Ph)1.637F Cl2-CF33-(3-Cl-4-F-Ph)1.638F Cl2-CF33-(4-F-Ph)1.639Cl 1.640 Cl Cl 2-CF3 3-(2-CI-Ph) Cl2-CF33-(4-Cl-Ph)1.641Cl 1.642 Cl Cl 2-CF3 3-(3-CF3-Ph) Cl2-CF33-(4-CF3-Ph)1.643Cl Cl2-CF33-(2-CH3-Ph)1.644Cl Cl2-CF33-(3-CH3-Ph)1.645Cl Cl2-CF33-(4-CH3-Ph)1.646Cl Cl2-CF33-(3-OCF3-Ph)1.647Cl Cl2-CF33-(4-OCF3-Ph)1.648Cl Cl2-CF33-(4-t-butyl-Ph)1.649Cl 1.650 Cl Cl 2-CF3 3-(2, 4-CI2-Ph) No. X, X2 R, R2 Phys. data Cl2-CF33-(3,5-Cl2-Ph)1.651Cl Cl2-CF33-(2,4-F2-Ph)1.652Cl Cl2-CF33-(3,5-F2-Ph)1.653Cl 1.654 Cl Cl 2-CF3 3-(2-CF3-Ph) 1.655 Cl Cl 2-CF3 3-(4-OCH3-Ph) 1.656 Cl Cl 2-CF3 3-(4-SCH3-Ph) 1.657 Cl Cl 2-CF3 3-(3-OCH3-Ph) 1.658 Cl Cl 2-CF3 3-(3-CI-Ph) Cl2-CF33-(3,4-Cl2-Ph)1.659Cl Cl2-CF33-(3-Cl-4-F-Ph)1.660Cl Table 2: Compounds of the formula No. X, X2 R, R2 Phys. data 2.1FFH4- (4-F-Ph) 213-215° FH4-(2-Cl-Ph)2.2F FH4-(4-Cl-Ph)230-232°2.3F FH4-(3-CF3-Ph)215-216°2.4F 2.5FFH4- (4-CF3-Ph) 251-252° FH4-(2-CH3-Ph)2.6F FH4-(3-CH3-Ph)2.7F FH4-(4-CH3-Ph)205-207°2.8F FH4-(3-OCF3-Ph)2.9F 2.10FFH4- (4-OCF3-Ph) 232-234° FH4-(4-t-butyl-Ph)2.11F FH4-(2,4-Cl2-Ph)2.12F FH4-(3,5-Cl2-Ph)242-243°2.13F FH4-(2,4-F2-Ph)2.14F FH4-(3,5-F2-Ph)2.15F FH4-(2-CF3-Ph)2.16F No. X, X2 R, R2 Phys. data FH4-(4-OCH3-Ph)237-238°2.17F 2.18 F F H 4- (4-SCH3-Ph) FH4-(3-OCH3-Ph)204-205°2.19F FH4-(3-Cl-Ph)209-210°2.20F 2.21 F F H 4- (3, 4-CI2-Ph) FH4-(3-Cl-4-F-Ph)239-242°2.22F ClH4-(4-F-Ph)2.23F 2.24 F Cl H 4-(2-CI-Ph) ClH4-(4-Cl-Ph)2.25F ClH4-(3-CF3-Ph)2.26F 2.27 F Cl H 4- (4-CF3-Ph) 227-230 ClH4-(2-CH3-Ph)2.28F 2.29 F Cl H 4- (3-CH3-Ph) ClH4-94-CH3-Ph)2.30F ClH4-(3-OCF3-Ph)2.31F ClH4-(4-OCF3-Ph)198-2002.32F ClH4-(4-t-butyl-Ph)2.33F 2.34 F Cl H 4-(2, 4-CI2-Ph) ClH4-(3,5-Cl2-Ph)2.35F 2.36 F Cl H 4-(2, 4-F2-Ph) 2.37 F Cl H 4- (3,5-F2-Ph) ClH4-(2-CH3-Ph)2.38F ClH4-(4-OCH3-Ph)2.39F ClH4-(4-SCH3-Ph)2.40F ClH4-(3-OCH3-Ph)2.41F ClH4-(3-Cl-Ph)2.42F ClH4-(3,4-Cl2-Ph)2.43F ClH4-(3-Cl-4-F-Ph)2.44F ClH4-(4-F-Ph)2.45Cl ClH4-(2-Cl-Ph)2.46Cl ClH4-(4-Cl-Ph)192-195°2.47Cl ClH4-(3-CF3-Ph)2.48Cl ClH4-(4-CF3-Ph)214-215°2.49Cl No. X, X2 R, R2 Phys. data 2.50 Cl Cl H 4-(2-CH3-Ph) 2.51 Cl Cl H 4-(3-CH3-Ph) ClH4-(4-CH3-Ph)2.52Cl ClH4-(3-OCF3-Ph)2.53Cl ClH4-(4-OCF3-Ph)155-159°2.54Cl ClH4-(4-t-butyl-Ph)1.55Cl 2.56 Cl Cl H 4-(2, 4-CI2-Ph) ClH4-(3,5-Cl2-Ph).2.57Cl 2.58 Cl Cl H 4-(2, 4-F2-Ph) ClH4-(3,5-F2-Ph)2.59Cl 2.60 Cl Cl H 4-(2-CF3-Ph) ClH4-(4-OCH3-Ph)2.61Cl ClH4-(4-SCH3-Ph)2.62Cl ClH4-(3-OCH3-Ph)2.63Cl ClH4-(3-Cl-Ph)2.64Cl ClH4-(3,4-Cl2-Ph)2.65Cl ClH4-(3-Cl-4-F-Ph)2.66Cl 2.67FFH3- (4-F-Ph) 155-157° FH3-(2-Cl-Ph)2.68F FH3-(4-Cl-Ph)140-141°2.69F 2.70FFH3- (3-CF3-Ph) 165-167° FH3-(4-CF3-Ph)162-168°2.71F FH3-(2-CH3-Ph)2.72F FH3-(3-CH3-Ph)2.73F FH3-(4-CH3-Ph)178-179°2.74F FH3-(3-OCF3-Ph)2.75F 2.76FFH3- (4-OCF3-Ph) 149-150° FH3-(4-t-butyl-Ph)2.77F FH3-(2,4-Cl2-Ph)2.78F FH3-(3,5-Cl2-Ph)187-189°2.79F 2.80 F F H 3-(2, 4-F2-Ph) FH3-(3,5-F2-Ph)2.81F FH3-(2-CF3-Ph)2.82F No. X, X2 R, R2 Phys. data FH3-(4-OCH3-Ph)208-210°2.83F 2.84 F F H 3- (4-SCH3-Ph) FH3-(3-OCH3-Ph)165-166°2.85F FH3-(3-Cl-Ph)162-163°2.86F FH3-(3,4-Cl2-Ph)2.87F 2.88 F F H 3- (3-CI-4-F-Ph) ClH3-(4-F-Ph)2.89F ClH3-(2-Cl-Ph)2.90F ClH3-(4-Cl-Ph)2.91F 2.92 F Cl H 3- (3-CF3-Ph) ClH3-(4-CF3-Ph)2.93F 2.94 F Cl H 3-(2-CH3-Ph) ClH3-(3-CH3-Ph)2.95F 2.96 F Cl H 3- (4-CH3-Ph) ClH3-(3-OCF3-Ph)2.97F ClH3-(4-OCF3-Ph)2.98F ClH3-(4-t-butyl-Ph)2.99F ClH3-(2,4-Cl2-Ph)2.100F 2.101 F Cl H 3- (3, 5-CI2-Ph) ClH3-(2,4-F2-Ph)2.102F 2.103 F Cl H 3- (3, 5-F2-Ph) ClH3-(2-CF3-Ph)2.104F 2.105 F Cl H 3- (4-OCH3-Ph) 2.106 F Cl H 3- (4-SCH3-Ph) 2.107 F Cl H 3- (3-OCH3-Ph) ClH3-(3-Cl-Ph)2.108F ClH3-(3,4-Cl2-Ph)2.109F ClH3-(3-Cl-4-F-Ph)2.110F ClH3-(4-F-Ph)2.111Cl 2.112H3-(2-Cl-Ph)Cl ClH3-(4-Cl-Ph)2.113Cl ClH3-(3-CF3-Ph)2.114Cl ClH3-(4-CF3-Ph)2.115Cl No. X, X2 R, R2 Phys. data 2.116 Cl Cl H 3- (2-CH3-Ph) 2.117 Cl Cl H 3- (3-CH3-Ph) 2.118 Cl Cl H 3- (4-CH3-Ph) ClH3-(3-OCF3-Ph)2.119Cl 2.120 Cl Cl H 3- (4-OCF3-Ph) ClH3-(4-t-butyl-Ph)1.212Cl 2.122 Cl Cl H 3-(2, 4-CI2-Ph) ClH3-(3,5-Cl2-Ph)2.123Cl 2.124 Cl Cl H 3- (2, 4-F2-Ph) ClH3-(3,5-F2-Ph)2.125Cl ClH3-(2-CF3-Ph)2.126Cl 2.127 Cl Cl H 3- (4-OCH3-Ph) 2.128 Cl Cl H 3- (4-SCH3-Ph) 2.129 Cl Cl H 3- (3-OCH3-Ph) ClH3-(3-Cl-Ph)2.130Cl ClH3-(3,4-Cl2-Ph)2.131Cl ClH3-(3-Cl-4-F-Ph)2.132Cl F2-CH34-(4-F-Ph)2.133F F2-CH34-(2-Cl-Ph)2.134F F2-CH34-(4-Cl-Ph)2.135F F2-CH34-(3-CF3-Ph)2.136F F2-CH34-(4-CF3-Ph)2.137F F2-CH34-(2-CH3-Ph)2.138F F2-CH34-(3-CH3-Ph)2.139F F2-CH34-(4-CH3-Ph)2.140F F2-CH34-(3-OCF3-Ph)2.141F F2-CH34-(4-OCF3-Ph)2.142F F2-CH34-(4-t-butyl-Ph)2.143F F2-CH34-(2,4-Cl2-Ph)2.144F F2-CH34-(3,5-Cl2-Ph)2.145F 2.146FF2-CH34- (2, 4-F2-Ph) F2-CH34-(2,5-F2-Ph)2.147F F2-CH34-(2-CF3-Ph)2.148F No. X, X2 R, R2 Phys. data F2-CH34-(4-OCH3-Ph)2.149F F2-CH34-(4-SCH3-Ph)2.150F F2-CH34-(3-OCH3-Ph)2.151F F2-CH34-(3-Cl-Ph)2.152F 2.153FF2-CH34- (3, 4-C) 2-Ph) F2-CH34-(3-Cl-4-F-Ph)2.154F Cl2-CH34-(4-F-Ph)2.155F 2.156 F Cl 2-CH3 4-(2-CI-Ph) Cl2-CH34-(4-Cl-Ph)2.157F Cl2-CH34-(3-CF3-Ph)2.158F Cl2-CH34-(4-CF3-Ph)2.159F 2.160 F Cl 2-CH3 4-(2-CH3-Ph) Cl2-CH34-(3-CH3-Ph)2.161F Cl2-CH34-(4-CH3-Ph)2.162F Cl2-CH34-(3-OCF3-Ph)2.163F Cl2-CH34-(4-OCF3-Ph)2.164F Cl2-CH34-(4-t-butyl-Ph)2.165F 2.166 F Cl 2-CH3 4-(2, 4-CI2-Ph) Cl2-CH34-(3,5-Cl2-Ph)2.167F 2.168 F Cl 2-CH3 4-(2, 4-F2-Ph) Cl2-CH34-(3,5-F2-Ph)2.169F 2.170 F Cl 2-CH3 4-(2-CF3-Ph) Cl2-CH34-(4-OCH3-Ph)2.171F Cl2-CH34-(4-SCH3-Ph)2.172F Cl2-CH34-(3-OCH3-Ph)2.173F Cl2-CH34-(3-Cl-Ph)2.172F Cl2-CH34-(3,4-Cl2-Ph)2.175F Cl2-CH34-(3-Cl-4-F-Ph)2.176F Cl2-CH34-(4-F-Ph)2.177Cl Cl2-CH34-(2-Cl-Ph)2.178Cl Cl2-CH34-(4-Cl-Ph)2.179Cl Cl2-CH34-(3-CF3-Ph)2.180Cl 2.181 CI Cl 2-CH3 4-(4-CF3-Ph) No. X, X2 R, R2 Phys. data 2.182 Cl Cl 2-CH3 4-(2-CH3-Ph) Cl2-CH34-(3-CH3-Ph)2.183Cl Cl2-CH34-(4-CH3-Ph)2.184Cl Cl2-CH34-(3-OCF3-Ph)2.185Cl Cl2-CH34-(4-OCF3-Ph)2.186Cl Cl2-CH34-(4-t-butyl-Ph)2.187Cl Cl2-CH34-(2,4-Cl2-Ph)2.188Cl 2.189 Cl Cl 2-CH3 4-(3, 5-CI2-Ph) 2.190 Cl Cl 2-CH3 4-(2, 4-F2-Ph) Cl2-CH34-(3,5-F2-Ph)2.191Cl 2.192 Cl Cl 2-CH3 4-(2-CF3-Ph) Cl2-CH34-(4-OCH3-Ph)2.193Cl Cl2-CH34-(4-SCH3-Ph)2.194Cl Cl2-CH34-(3-OCH3-Ph)2.195Cl Cl2-CH34-(3-Cl-Ph)2.196Cl 2.197 Cl Cl 2-CH3 4-(3, 4-CI2-Ph) Cl2-CH34-(3-Cl-4-F-Ph)2.198Cl F2-CH33-(4-F-Ph)2.199F F2-CH33-(2-Cl-Ph)2.200F F2-CH33-(4-Cl-Ph)2.201F F2-CH33-(3-CF3-Ph)2.202F F2-CH33-(4-CF3-Ph)2.203F F2-CH33-(2-CH3-Ph)2.204F F2-CH33-(3-CH3-Ph)2.205F F2-CH33-(4-CH3-Ph)2.206F F2-CH33-(3-OCF3-Ph)2.207F F2-CH33-(4-OCF3-Ph)2.208F F2-CH33-(4-t-butyl-Ph)2.209F F2-CH33-(2,4-Cl2-Ph)2.210F F2-CH33-(3,5-Cl2-Ph)2.211F F2-CH33-(2,4-F2-Ph)2.212F F2-CH33-(3,5-F2-Ph)2.213F F2-CH33-(2-CF3-Ph)2.214F No. X, X2 R, R2 Phys. data F2-CH33-(4-OCH3-Ph)2.215F F2-CH33-(4-SCH3-Ph)2.216F F2-CH33-(3-OCH3-Ph)2.217F F2-CH33-(3-Cl-Ph)2.218F F2-CH33-(3,4-Cl2-Ph)2.219F F2-CH33-(3-Cl-4-F-Ph)2.220F 2.221 F Cl 2-CH3 3-(4-F-Ph) 2.222 F Cl 2-CH3 3-(2-CI-Ph) Cl-CH33-(4-Cl-Ph)2.223F Cl2-CH33-(3-CF3-Ph)2.224F Cl2-CH33-(4-CF3-Ph)2.225F 2.226 F Cl 2-CH3 3-(2-CH3-Ph) Cl2-CH33-(3-CH3-Ph)2.227F Cl2-CH33-(4-CH3-Ph)2.228F Cl2-CH33-(3-OCF3-Ph)2.229F Cl2-CH33-(4-OCF3-Ph)2.230F Cl2-CH33-(4-t-butyl-Ph)2.231F 2.232 F Cl 2-CH3 3-(2, 4-CI2-Ph) Cl2-CH33-(3,5-Cl2-Ph)2.233F 2.234 F Cl 2-CH3 3-(2, 4-F2-Ph) Cl2-CH33-(3,5-F2-Ph)2.235F 2.236 F Cl 2-CH3 3-(2-CF3-Ph) Cl2-CH33-(4-OCH3-Ph)2.237F Cl2-CH33-(4-SCH3-Ph)2.238F Cl2-CH33-(3-OCH3-Ph)2.239F Cl2-CH33-(3-Cl-Ph)2.240F Cl2-CH33-(3,4-Cl2-Ph)2.241F Cl2-CH33-(3-Cl-4-F-Ph)2.242F Cl2-CH33-(4-F-Ph)2.243Cl 2.244 Cl Cl 2-CH3 3-(2-CI-Ph) Cl2-CH33-(4-Cl-Ph)2.245Cl Cl2-CH33-(3-CF3-Ph)2.246Cl Cl2-CH33-(4-CF3-Ph)2.247Cl No. X, X2 R, R2 Phys. data 2.248 CI Cl 2-CH3 3-(2-CH3-Ph) Cl2-CH33-(3-CH3-Ph)2.249Cl Cl2-CH33-(4-CH3-Ph)2.250Cl 2.251 CI Cl 2-CH3 3-(3-OCF3-Ph) 2.252 Cl Cl 2-CH3 3-(4-OCF3-Ph) Cl2-CH33-(4-t-butyl-Ph)2.253Cl Cl2-CH33-(2,4-Cl2-Ph)2.254Cl Cl2-CH33-(3,5-Cl2-Ph)2.255Cl Cl2-CH33-(2,4-F2-Ph)2.256Cl Cl2-CH33-(3,5-F2-Ph)2.257Cl Cl2-CH33-(2-CF3-Ph)2.258Cl Cl2-CH33-(4-OCH3-Ph)2.259Cl Cl2-CH33-(4-SCH3-Ph)2.260cl 2.261 CI Cl 2-CH3 3-(3-OCH3-Ph) Cl2-CH33-(3-Cl-Ph)2.262Cl Cl2-CH33-(3,4-Cl2-Ph)2.263Cl 2.264 CI Cl 2-CH3 3- (3-CI-4-F-Ph) F2-Cl4-(4-F-Ph)2.265F F2-Cl4-(2-Cl-Ph)2.266F F2-Cl4-(4-Cl-Ph)2.267F F2-Cl4-(3-CF3-Ph)2.268F F2-Cl4-(4-CH3-Ph)2.269F F2-Cl4-(2-CH3-Ph)2.270F F2-Cl4-(4-CH3-Ph)2.271F F2-Cl4-(4-CH3-Ph)2.272F F2-Cl4-(3-OCF3-Ph)2.273F F2-Cl4-(4-OCF3-Ph)2.274F F2-Cl4-(4-t-butyl-Ph)2.275F F2-Cl4-(2,4-Cl2-Ph)2.276F F2-Cl4-(3,5-Cl2-Ph)2.277F F2-Cl4-(2,4-F2-Ph)2.278F F2-Cl4-(3,5-F2-Ph)2.279F F2-Cl4-(2-CF3-Ph)2.280F No. X, X2 R, R2 Phys. data F2-Cl4-(4-OCH3-Ph)2.281F 2.282FF2-C ! 4- (4-SCHs-Ph) F2-Cl4-(3-OCH3-Ph)2.283F F2-Cl4-(3-Cl-Ph)2.284F F2-Cl4-(3,4-Cl2-Ph)2.285F F2-Cl4-(3-Cl-4-F-Ph)2.286F Cl2-Cl4-(4-F-Ph)2.287F Cl2-Cl4-(2-Cl-Ph)2.288F 2.289 F Cl 2-CI 4-(4-CI-Ph) Cl2-Cl4-(3-CF3-Ph)2.290F Cl2-Cl4-(4-CF3-Ph)2.291F 2.292 F Cl 2-CI 4-(2-CH3-Ph) Cl2-Cl4-(3-CH3-Ph)2.293F Cl2-Cl4-(4-CH3-Ph)2.294F Cl2-Cl4-(3-OCF3-Ph)2.295F Cl2-Cl4-(4-OCF3-Ph)2.296F 2.297 F Cl 2-CI 4-(4-t-butyl-Ph) 2.298 F Cl 2-CI 4-(2, 4-CI2-Ph) Cl2-Cl4-(3,5-Cl2-Ph)2.299F 2.300 F Cl 2-CI 4-(2, 4-F2-Ph) Cl2-Cl4-(3,5-F2-Ph)2.301F 2.302 F Cl 2-CI 4-(2-CF3-Ph) Cl2-Cl4-(4-OCH3-Ph)2.303F Cl2-Cl4-(4-SCH3-Ph)2.304F Cl2-Cl4-(3-OCH3-Ph)2.305F Cl2-Cl4-(3-Cl-Ph)2.306F Cl2-Cl4-(3,4-Cl2-Ph)2.307F 2.308 F Cl 2-CI 4-(3-CI-4-F-Ph) 2.309 Cl Cl 2-CI 4- (4-F-Ph) 2.3102-Cl4-(2-Cl-Ph)Cl Cl2-Cl4-(4-Cl-Ph)2.311Cl 2.312 Cl Cl 2-Cl 4- (3-CF3-Ph) Cl2-Cl4-(4-CF3-Ph)2.313Cl No. X, X2 R, R2 Phys. data 2.314 Cl Cl 2-CI 4-(2-CH3-Ph) Cl2-Cl4-(3-CH3-Ph)2.315Cl Cl2-Cl4-(4-CH3-Ph)2.316Cl Cl2-Cl4-(3-OCF3-Ph)2.317Cl Cl2-Cl4-(4-OCF3-Ph)2.318Cl Cl2-Cl4-(4-t-butyl-Ph)2.319Cl 2.320 Cl Cl 2-CI 4-(2, 4-CI2-Ph) Cl2-Cl4-(3,5-Cl2-Ph)2.321Cl 2.322 Cl Cl 2-CI 4-(2, 4-F2-Ph) Cl2-Cl4-(3,5-F2-Ph)2.323Cl Cl2-Cl4-(2-CF3-Ph)2.324Cl Cl2-Cl4-(4-OCH3-Ph)2.325Cl Cl2-Cl4-(4-SCH3-Ph)2.326Cl Cl2-Cl4-(3-OCH3-Ph)2.327Cl Cl2-Cl4-(3-Cl-Ph)2.328Cl Cl2-Cl4-(3,4-Cl2-Ph)2.329Cl Cl2-Cl4-(3-Cl-4-F-Ph)2.330Cl F2-Cl3-(4-F-Ph)2.331F 2.332 F F 2-CI 3-(2-CI-Ph) F2-Cl3-(4-Cl-Ph)2.333F F2-Cl3-(3-CF3-Ph)2.334F F2-Cl3-(4-CF3-Ph)2.335F 2.336 F F 2-CI 3-(2-CH3-Ph) F2-Cl3-(3-CH3-Ph)2.337F 2-Cl3-(4-CH3-Ph)2.338F F2-Cl3-(3-OCF3-Ph)2.339F F2-Cl3-(4-OCF3-Ph)2.340F F2-Cl3-(4-t-butyl-Ph)2.341F F2-Cl3-(2,4-Cl2-Ph)2.342F F2-Cl3-(3,5-Cl2-Ph)2.343F F2-Cl3(2,4-F2-Ph)2.344F F2-Cl3-(4,5-F2-Ph)2.345F 2.346 F F 2-CI 3-(2-CF3-Ph) No. X, X2 R, R2 Phys. data F2-Cl3-(4-OCH3-Ph)2.347F F2-Cl3-(4-SCH3-Ph)2.348F F2-Cl3-(3-OCH3-Ph)2.349F F2-Cl3-(3-Cl-Ph)2.350F F2-Cl3-(3,4-Cl2-Ph)2.351F F2-Cl3-(3-Cl-4-F-Ph)2.352F 2.353 F Cl 2-CI 3-(4-F-Ph) 2.354 F Cl 2-CI 3-(2-CI-Ph) Cl2-Cl3-(4-Cl-Ph)2.355F Cl2-Cl3-(3-CF3-Ph)2.356F Cl2-Cl3-(4-CF3-Ph)2.357F 2.358 F Cl 2-CI 3-(2-CH3-Ph) 2.359 F Cl 2-CI 3-(3-CH3-Ph) Cl2-Cl3-(4-CH3-Ph)2.360F Cl2-Cl3-(3-OCF3-Ph)2.361F Cl2-Cl3-(4-OCF3-Ph)2.362F Cl2-Cl3-(4-t-butyl-Ph)2.363F 2.364 F Cl 2-CI 3-(2, 4-CI2-Ph) Cl2-Cl3-(3,5-Cl2-Ph)2.365F 2.366 F Cl 2-CI 3-(2, 4-F2-Ph) Cl2-Cl3-(3,5-F2-Ph)2.367F 2.368 F Cl 2-CI 3-(2-CF3-Ph) Cl2-Cl3-(4-OCH3-Ph)2.369F Cl2-Cl3-(4-SCH3-Ph)2.370F Cl2-Cl3-(3-OCH3-Ph)2.371F Cl2-Cl3-(3-Cl-Ph)2.372F Cl2-Cl3-(3,4-Cl2-Ph)2.373F Cl2-Cl3-(3-Cl-4-F-Ph)2.374F Cl2-Cl3-(4-F-Ph)2.375Cl 2.376 Cl Cl 2-CI 3-(2-CI-Ph) Cl2-Cl3-(4-Cl-Ph)2.377Cl Cl2-Cl3-(3-CF3-Ph)2.378Cl Cl2-Cl3-(4-CF3-Ph)2.379Cl No. X, X2 R, R2 Phys. data 2.380 Cl Cl 2-CI 3-(2-CH3-Ph) Cl2-Cl3-(3-CH3-Ph)2.381Cl Cl2-Cl3-(4-CH3-Ph)2.382Cl Cl2-Cl3-(3-OCF3-Ph)2.383Cl Cl2-Cl3-(4-OCF3-Ph)2.384Cl Cl2-Cl3-(4-t-butyl-Ph)2.385Cl 2.386 Cl Cl 2-CI 3-(2, 4-CI2-Ph) Cl2-Cl3-(3,5-Cl2-Ph)2.387Cl 2.388 Cl Cl 2-CI 3-(2, 4-F2-Ph) Cl2-Cl3-(3,5-F2-Ph)2.389Cl 2.390 Cl Cl 2-CI 3-(2-CF3-Ph) 2.391 Cl Cl 2-CI 3-(4-OCH3-Ph) Cl2-Cl3-(4-SCH3-Ph)2.392Cl Cl2-Cl3-(3-OCH3-Ph)2.393Cl Cl2-Cl3-(3-Cl-Ph)2.394Cl Cl2-Cl3-(3,4-Cl2-Ph)2.395Cl Cl2-Cl3-(3-Cl-4-F-Ph)2.396Cl F2-OCH34-(4-F-Ph)2.397F F2-OCH34-(2-Cl-Ph)2.398F F2-OCH34-(4-Cl-Ph)2.399F F2-OCH34-(3-CF3-Ph)2.400F F2-OCH34-(4-CF3-Ph)2.401F F2-OCH34-(2-CH3-Ph)2.402F F2-OCH34-(3-CH3-Ph)2.403F F2-OCH34-(4-CH3-Ph)2.404F F2-OCH34-(3-OCF3-Ph)2.405F F2-OCH34-(4-OCF3-Ph)2.406F F2-OCH34-(4-t-butyl-Ph)2.407F 2.408 F F 2-OCH3 4-(2, 4-CI2-Ph) F2-OCH34-(3,5-Cl2-Ph)2.409F 2.410FF2-OCH34- (2, 4-F2-Ph) F2-OCH34-(3,5-F2-Ph)2.411F F2-OCH34-(2-CF3-Ph)2.412F No. X, X2 R, R2 Phys. data F2-OCH34-(4-OCH3-Ph)2.413F F2-OCH34-(4-SCH3-Ph)2.414F F2-OCH34-(3-OCH3-Ph)2.415F F2-OCH34-(3-Cl-Ph)2.416F F2-OCH34-(3,4-Cl2-Ph)2.417F F2-OCH34-(3-Cl-4-F-Ph)2.418F Cl2-OCH34-(4-F-Ph)2.419F 2.420 F Cl 2-OCH3 4-(2-CI-Ph) Cl2-OCH34-(4-Cl-Ph)2.421F Cl2-OCH34-(3-CF3-Ph)2.422F Cl2-OCH34-(4-CF3-Ph)2.423F 2.424 F Cl 2-OCH3 4-(2-CH3-Ph) Cl2-OCH34-(3-CH3-Ph)2.425F Cl2-OCH34-(4-CH3-Ph)2.426F Cl2-OCH34-(3-OCF3-Ph)2.427F Cl2-OCH34-(4-OCF3-Ph)2.428F Cl2-OCH34-(4-t-butyl-Ph)2.429F 2.430 F Cl 2-OCH3 4-(2, 4-CI2-Ph) Cl2-OCH34-(3,5-Cl2-Ph)2.431F 2.432 F Cl 2-OCH3 4-(2, 4-F2-Ph) Cl2-OCH34-(3,5-F2-Ph)2.433F 2.434 F Cl 2-OCH3 4-(2-CF3-Ph) Cl2-OCH34-(4-OCH3-Ph)2.435F Cl2-OCH34-(4-SCH3-Ph)2.436F Cl2-OCH34-(3-OCH3-Ph)2.437F 2.438 F Cl 2-OCH3 4-(3-CI-Ph) Cl2-OCH34-(3,4-Cl2-Ph)2.439F Cl2-OCH34-(3-Cl-4-F-Ph)2.440F Cl2-OCH34-(4-F-Ph)2.441Cl 2.442 Cl Cl 2-OCH3 4-(2-CI-Ph) Cl2-OCH34-(4-Cl-Ph)2.443Cl Cl2-OCH34-(3-CF3-Ph)2.444Cl Cl2-OCH34-(4-CF3-Ph)2.445Cl No. X, X2 R, R2 Phys. data 2.446 Cl Cl 2-OCH3 4-(2-CH3-Ph) 2.447 Cl Cl 2-OCH3 4-(3-CH3-Ph) 2.448 Cl Cl 2-OCH3 4-(4-CH3-Ph) Cl2-OCH34-(3-OCF3-Ph)2.449Cl Cl2-OCH34-(4-OCF3-Ph)2.450Cl Cl2-OCH34-(4-t-butyl-Ph)2.451Cl 2.452 Cl Cl 2-OCH3 4-(2, 4-CI2-Ph) Cl2-OCH34-(3,5-Cl2-Ph)2.453Cl 2.454 Cl Cl 2-OCH3 4-(2,4-F2-Ph) Cl2-OCH34-(3,5-F2-Ph)2.455Cl 2.456 Cl Cl 2-OCH3 4-(2-CF3-Ph) Cl2-OCH34-(4-OCH3-Ph)2.457Cl Cl2-OCH34-(4-SCH3-Ph)2.458Cl Cl2-OCH34-(3-OCH3-Ph)2.459Cl Cl2-OCH34-(3-Cl-Ph)2.460Cl Cl2-OCH34-(3,4-Cl2-Ph)2.461Cl Cl2-OCH34-(3-Cl-4-F-Ph)2.462Cl F2-OCH33-(4-F-Ph)2.463F F2-OCH33-(2-Cl-Ph)2.464F F2-OCH33-(4-Cl-Ph)2.465F F2-OCH33-(3-CF3-Ph)2.466F F2-OCH33-(4-CF3-Ph)2.467F F2-OCH33-(2-CH3-Ph)2.468F F2-OCH33-(3-CH3-Ph)2.469F F2-OCH33-(4-CH3-Ph)2.470F F2-OCH33-(3-OCF3-Ph)2.471F F2-OCH33-(4-OCF3-Ph)2.472F F2-OCH33-(4-t-butyl-Ph)2.473F F2-OCH33-(2,4-Cl2-Ph)2.474F F2-OCH33-(3,5-Cl2-Ph)2.475F F2-OCH33-(2,4-F2-Ph)2.476F F2-OCH33-(3,5-F2-Ph)2.477F F2-OCH33-(2-CF3-Ph)2.478F No. X, X2 R, R2 Phys. data F2-OCH33-(4-OCH3-Ph)2.479F F2-OCH33-(4-SCH3-Ph)2.480F F2-OCH33-(3-OCH3-Ph)2.481F F2-OCH33-(3-Cl-Ph)2.482F F2-OCH33-(3,4-Cl2-Ph)2.483F F2-OCH33-(3-Cl-4-F-Ph)2.484F Cl2-OCH33-(4-F-Ph)2.45F 2.486 F Cl 2-OCH3 3-(2-CI-Ph) 2.487 F Cl 2-OCH3 3-(4-CI-Ph) Cl2-OCH33-(3-CF3-Ph)2.488F 2.489 F Cl 2-OCH3 3-(4-CF3-Ph) Cl2-OCH33-(2-CH3-Ph)2.490F Cl2-OCH33-(3-CH3-Ph)2.491F Cl2-OCH33-(4-CH3-Ph)2.492F Cl2-OCH33-(3-OCF3-Ph)2.493F Cl2-OCH33-(4-OCF3-Ph)2.494F Cl2-OCH33-(4-t-butyl-Ph)2.495F 2.496 F Cl 2-OCH3 3-(2, 4-CI2-Ph) Cl2-OCH33-(3,5-Cl2-Ph)2.497F 2.498 F Cl 2-OCH3 3-(2, 4-F2-Ph) Cl2-OCH33-(3,5-F2-Ph)2.499F 2.500 F Cl 2-OCH3 3-(2-CF3-Ph) Cl2-OCH33-(4-OCH3-Ph)2.501F Cl2-OCH33-(4-SCH3-Ph)2.502F Cl2-OCH33-(3-OCH3-Ph)2.503F Cl2-OCH33-(3-Cl-Ph)2.504F Cl2-OCH33-(3,4-Cl2-Ph)2.505F Cl2-OCH33-(3-Cl-4-F-Ph)2.506F Cl2-OCH33-(4-F-Ph)2.507Cl 2.508 Cl Cl 2-OCH3 3-(2-CI-Ph) Cl2-OCH33-(4-Cl-Ph)2.509Cl Cl2-OCH33-(3-CF3-Ph)2.510Cl Cl2-OCH33-(4-CF3-Ph)2.511Cl No. X, X2 R, R2 Phys. data 2.512 Cl Cl 2-OCH3 3-(2-CH3-Ph) Cl2-OCH33-(3-CH3-Ph)2.513Cl 2.514 Cl Cl 2-OCH3 3-(4-CH3-Ph) 2.515 Cl Cl 2-OCH3 3-(3-OCF3-Ph) 2.516 Cl Cl 2-OCH3 3-(4-OCF3-Ph) Cl2-OCH33-(4-t-butyl-Ph)2.517Cl 2.518 Cl Cl 2-OCH3 3-(2, 4-CI2-Ph) 2.519 Cl Cl 2-OCH3 3-(3, 5-CI2-Ph) Cl2-OCH33-(2,4-F2-Ph)2.520Cl 2.521 CI Cl 2-OCH3 3-(3, 5-F2-Ph) 2.522 Cl Cl 2-OCH3 3-(2-CF3-Ph) Cl2-OCH33-(4-OCH3-Ph)2.523Cl Cl2-OCH33-94-SCH3-Ph)2.524Cl Cl2-OCH33-(3-OCH3-Ph)2.525Cl 2.526 Cl Cl 2-OCH3 3-(3-CI-Ph) Cl2-OCH33-(3,4-Cl2-Ph)2.527Cl Cl2-OCH33-(3-Cl-4-F-Ph)2.528Cl F2-CF34-(4-F-Ph)2.529F F2-CF34-(2-Cl-Ph)2.530F F2-CF34-(4-Cl-Ph)2.531F F2-CF34-(3-CF3-Ph)2.532F F2-CF34-(4-CF3-Ph)2.533F F2-CF34-(2-CH3-Ph)2.534F F2-CF34-(3-CH3-Ph)2.535F F2-CF34-(4-CH3-Ph)2.536F F2-CF34-(3-OCF3-Ph)2.537F F2-CF34-(4-OCF3-Ph)2.538F F2-CF34-(4-t-butyl-Ph)2.539F F2-CF34-(2,4-Cl2-Ph)2.540F F2-CF34-(3,5-Cl2-Ph)2.541F 2.542FF2-CF34- (2, 4-F2-Ph) F2-CF34-(3,5-F2-Ph)2.543F F2-CF34-(2-CF3-Ph)2.544F No. X, X2 R, R2 Phys. data F2-CF34-(4-OCH3-Ph)2.545F F2-CF34-(4-SCH3-Ph)2.546F F2-CF34-(3-OCH3-Ph)2.547F F2-CF34-(3-Cl-Ph)2.548F F2-CF34-(3,4-Cl2-Ph)2.549F F2-CF34-(3-Cl-4-F-Ph)2.550F Cl2-CF34-(4-F-Ph)2.551F 2.552 F Cl 2-CF3 4-(2-CI-Ph) 2.553 F Cl 2-CF3 4-(4-CI-Ph) Cl2-CF34-(3-CF3-Ph)2.554F Cl2-CF34-(4-CF3-Ph)2.555F 2.556 F Cl 2-CF3 4-(2-CH3-Ph) Cl2-CF34-(3-CH3-Ph)2.557F Cl2-CF34-(4-CH3-Ph)2.558F Cl2-CF34-(3-OCF3-Ph)2.559F Cl2-CF34-(4-OCF3-Ph)2.560F Cl2-CF34-(4-t-butyl-Ph)2.561F 2.562 F Cl 2-CF3 4-(2, 4-CI2-Ph) Cl2-CF34-(3,5-Cl2-Ph)2.563F 2.564 F Cl 2-CF3 4-(2,4-F2-Ph) Cl2-CF34-(3,5-F2-Ph)2.565F 2.566 F Cl 2-CF3 4-(2-CF3-Ph) Cl2-CF34-(4-OCH3-Ph)2.567F Cl2-CF34-(4-SCH3-Ph)2.568F Cl2-CF34-(3-OCH3-Ph)2.569F Cl2-CF34-(3-Cl-Ph)2.570F Cl2-CF34-(3,4-Cl2-Ph)2.571F Cl2-CF34-(3-Cl-4-F-Ph)2.572F Cl2-CF34-(4-F-Ph)2.573Cl 2.574 Cl Cl 2-CF3 4-(2-CI-Ph) Cl2-CF34-(4-Cl-Ph)2.575Cl Cl2-CF34-(3-CF3-Ph)2.576Cl Cl2-CF34-(4-CF3-Ph)2.577Cl No. X, X2 R, R2 Phys. data 2.578 Cl Cl 2-CF3 4-(2-CH3-Ph) Cl2-CF34-(3-CH3-Ph)2.579Cl 2.580 Cl Cl 2-CF3 4-(4-CH3-Ph) Cl2-CF34-(3-OCF3-Ph)2.581Cl 2.582 Cl Cl 2-CF3 4-(4-OCF3-Ph) Cl2-CF34-(4-t-butyl-Ph)2.583Cl 2.584 Cl Cl 2-CF3 4-(2, 4-CI2-Ph) Cl2-CF34-(3,5-Cl2-Ph)2.585Cl 2.586 Cl Cl 2-CF3 4-(2, 4-F2-Ph) Cl2-CF34-(3,5-F2-Ph)2.587Cl 2.588 Cl Cl 2-CF3 4-(2-CF3-Ph) Cl2-CF34-(4-OCH3-Ph)2.589Cl Cl2-CF34-(4-SCH3-Ph)2.590Cl Cl2-CF34-(3-OCH3-Ph)2.591Cl Cl2-CF34-(3-Cl-Ph)2.592Cl Cl2-CF34-(3,4-Cl2-Ph)2.593Cl Cl2-CF34-(3-Cl-4-F-Ph)2.594Cl F2-CF33-(4-F-Ph)2.595F F2-CF33-(2-Cl-Ph)2.596F F2-CF33-(4-Cl-Ph)2.597F F2-CF33-(3-CF3-Ph)2.598F F2-CF33-(4-CF3-Ph)2.599F F2-CF33-(2-CH3-Ph)2.600F F2-CF33-(3-CH3-Ph)2.601F F2-CF33-(4-CH3-Ph)2.602F F2-CF33-(3-OCF3-Ph)2.603F F2-CF33-(4-OCF3-Ph)2.604F F2-CF33-(4-t-butyl-Ph)2.605F F2-CF33-(2,4-Cl2-Ph)2.606F F2-CF33-(3,5-Cl2-Ph)2.607F F2-CF33-(2,4-F2-Ph)2.608F F2-CF33-(3,5-F2-Ph)2.609F F2-CF33-(2-CF3-Ph)2.610F No. X, X2 R, R2 Phys. data F2-CF33-(4-OCH3-Ph)2.611F F2-CF33-(4-SCH3-Ph)2.612F F2-CF33-(3-OCH3-Ph)2.613F F2-CF33-(3-Cl-Ph)2.614F F2-CF33-(3,4-Cl2-Ph)2.615F F2-CF33-(3-Cl-4-F-Ph)2.616F Cl2-CF33-(4-F-Ph)2.167F 2.618 F Cl 2-CF3 3-(2-CI-Ph) 2.619 F Cl 2-CF3 3-(4-CI-Ph) Cl2-CF33-(3-CF3-Ph)2.620F Cl2-CF33-(4-CF3-Ph)2.621F 2.622 F Cl 2-CF3 3-(2-CH3-Ph) Cl2-CF33-(3-CH3-Ph)2.623F Cl2-CF33-(4-CH3-Ph)2.624F Cl2-CF33-(3-OCF3-Ph)2.625F Cl2-CF33-(4-OCF3-Ph)2.626F Cl2-CF33-(4-t-butyl-Ph)2.627F 2.628 F Cl 2-CF3 3-(2, 4-CI2-Ph) Cl2-CF33-(3,5-Cl2-Ph)2.629F 2.630 F Cl 2-CF3 3-(2, 4-F2-Ph) Cl2-CF33-(3,5-F2-Ph)2.631F 2.632 F Cl 2-CF3 3-(2-CF3-Ph) Cl2-CF33-(4-OCH3-Ph)2.633F Cl2-CF33-(4-SCH3-Ph)2.634F Cl2-CF33-(3-OCH3-Ph)2.635F Cl2-CF33-(3-Cl-Ph)2.636F Cl2-CF33-(3,4-Cl2-Ph)2.637F Cl2-CF33-(3-Cl-4-F-Ph)2.638F Cl2-CF33-(4-F-Ph)2.639Cl 2.640 Cl Cl 2-CF3 3-(2-CI-Ph) Cl2-CF33-(4-Cl-Ph)2.641Cl Cl2-CF33-(3-CF3-Ph)2.642Cl Cl2-CF33-(4-CF3-Ph)2.643Cl No. X, X2 R, R2 Phys. data Cl2-CF33-(2-CH3-Ph)2.644Cl 2.645 Cl Cl 2-CF3 3-(3-CH3-Ph) Cl2-CF33-(4-CH3-Ph)2.646Cl Cl2-CF33-(3-OCF3-Ph)2.647Cl Cl2-CF33-(4-OCF3-Ph)2.648Cl Cl2-CF33-(4-t-butyl-Ph)2.649Cl 2.650 Cl Cl 2-CF3 3-(2, 4-CI2-Ph) Cl2-CF33-(3,5-Cl2-Ph)2.651Cl 2.652 Cl Cl 2-CF3 3-(2, 4-F2-Ph) Cl2-CF33-(3,5-F2-Ph)2.653Cl Cl2-CF33-(2-CF3-Ph)2.654Cl Cl2-CF33-(4-OCH3-Ph)2.655Cl Cl2-CF33-(4-SCH3-Ph)2.656Cl Cl2-CF33-(3-OCH3-Ph)2.657Cl Cl2-CF33-(3-Cl-Ph)2.658Cl Cl2-CF33-(3,4-Cl2-Ph)2.659Cl Cl2-CF33-(3-Cl-4-F-Ph)2.660Cl Table 3: Compounds of the formula No. X1 X2 Rw Rv Phys. data 3.1 F F H 4-F 3.2 F F H 2-CI 3.3 F F H 4-CI 3.4 F F H 3-CF3 3.5 F F H 4-CF3 3.6 F F H 2-CH3 3.7 F F H 3-CH3 3.8 F F H 4-CH3 No. X1 X2 Rw Rv Phys. data 3.9 F F H 3-OCF3 3.10 F F H 4-OCF3 3.11 F F H 4-t-butyl 3.12 F F H 2, 4-CI2 FH3,5-Cl23.13F FH2,4-F2-Ph3.14F 3.15 F F H 3,5-F2 3.16 F F H 2-CF3 3.17 F F H 4-OCH3 3.18 F F H 4-SCH3 3.19 F F H 3-OCH3 3.20 F F H 3-CI FH3,4-Cl23.21F FH3-Cl-4-F3.22F 3.23 F F H 2-F ClH4-F3.24Cl ClH2-Cl3.25Cl ClH4-Cl3.26Cl ClH3-CF33.27Cl ClH4-CF33.28Cl 3.29 Cl ci H 2-CH3 3.30 ci ci H 3-CH3 ClH4-CH33.31Cl ClH3-OCF33.32Cl ClH4-OCF33.33Cl ClH4-t-butyl3.34Cl ClH2,4-Cl23.35Cl 3.36 CI CI H 3,5-Cl2 ClH2,4-F2-Ph3.37Cl ClH3,5-F23.38Cl 3.39 Cl Cl H 2-CF3 ClH4-OCH33.40Cl ClH4-SCH33.41Cl No. RwRvPhys.dataX2 ClH3-OCH33.42Cl 3.43 H3-ClCl ClH3,4-Cl23.44Cl ClH3-Cl-4-F3.45Cl 3.46 H2-FCl ClH4-F3.47F ClH2-Cl3.48F ClH4-Cl3.49F 3.50 F Cl H 3-CF3 ClH4-CF33.51F ClH2-CH33.52F ClH3-CH33.53F ClH4-CH33.54F ClH3-OCF33.55F 3.56 F Cl H 4-OCF3 3.57 F Cl H 4-t-butyl ClH2,4-Cl23.58F ClH3,50-Cl23.59F 3.60 F Cl H 2,4-F2-Ph ClH3,5-F23.61F ClH2-CF33.62F 3.63FCtH4-OCHs ClH4-SCH33.64F ClH3-OCH33.65F ClH3-Cl3.66F ClH3,4-Cl23.67F ClH3-Cl-4-F3.68F ClH2-F3.69F Table 4: Compounds of the formula No. X, X2 R, R2 Phys. data 4.1 F F H 4-F FH2-Cl4.2F 4.3 F F H 4-CI 4.4 F F H 3-CF3 4.5 F F H 4-CF3 4.6 F F H 2-CH3 4.7 F F H 3-CH3 4.8 F F H 4-CH3 4.9 F F H 3-OCF3 4.10 F F H 4-OCF3 4.11 F F H 4-t-butyl FH2,4-Cl24.12F FH3,5-Cl24.13F 4.14 F F H 2,4-F2-Ph 4.15 F F H 3,5-F2 4.16 F F H 2-CF3 4.17 F F H 4-OCH3 4.18 F F H 4-SCH3 4.19 F F H 3-OCH3 4.20 F F H 3-CI 4.21 F F H 3, 4-CI2 4.22 F F H 3-CI-4-F 4.23 F F H 2-F ClH4-F4.24Cl ClH2-Cl4.25Cl No. X, X2 R, R2 Phys. data 4.26 Cl ci H 4-CI 4.27 Cl ci H 3-CF3 ClH4-CF34.28Cl 4.29 ci Cl H 2-CH3 ClH3-CH34.30Cl ClH4-CH34.31Cl 4.32 Cl ci H 3-OCF3 4.33 Cl Cl H 4-OCF3 ClH4-t-butyl4.34Cl 4.35 CI Cl H 2, 4-CI2 4.36 CI Cl H 3,5-CI2 4.37 H2,4-F2-PhCl ClH3,5-F24.38Cl 4.39 H2-CF3Cl ClH4-OCH3.40Cl ClH4-SCH34.41Cl 4.42 H3-OCH3Cl 4.43 Cl Ci H 3-CI ClH3,4-Cl24.44Cl ClH3-Cl-4-F4.45Cl ClH2-F4.46Cl ClH4-F4.47F ClH2-Cl4.48F 4.49H4-ClCl ClH3-CF34.50F ClH4-CF34.51F ClH2-CH34.52F ClH3-CH34.53F ClH4-CH34.54F ClH3-OCF34.55F ClH4-OCF34.56F ClH4-t-butyl4.57F ClH2,4-Cl24.58F No. X, X2 R, R2 Phys. data 4.59 F Cl H 3, 5-C12 ClH2,4-F2-Ph4.60F ClH3,5-F24.61F ClH2-CF34.62F ClH4-OCH34.63F ClH4-SCH34.64F ClH3-OCH34.65F 4.66 F Cl H 3-CI ClH3,4-Cl24.67F 4.68 F CI H 3-CI-4-F ClH2-F4.69F Table 5: Compounds of the formula No. X, X2 X3 Rq Phys. data 5. 1 F F H -C(=O)C6H4-4-CH3 Smpt.: 196-197°C 5.2 F F H-C (=NOCH3) C6H4-3-CH3 Smpt.: 133-136°C 5.3 CH3 H H-C6H4-4-CF3 Smpt.: 224-227°C HH-C6H4-4-OCF35.4CH3 5.5 CH3 H H-C6H43-3, 4-CI2 5.6 CH3 H H-C6H4-3-CI HH-C6H3-3-Cl,4-F5.7CH3 5.8 CH3 H H-C6H4-4-SCH3 HH-C6H4-4-Cl5.9CH3 HH-C6H4-4-F5.10CH3 HH-C6H4-4-SCF35.11CH3 HF-C6H4-4-CF35.12Cl HF-C6H4-4-OCF35.13Cl HF-C6H43-3,4-Cl25.14Cl 5.15 Cl H F-C6H4-3-CI No. X, X2 X3 Rq Phys. data HF-C6H3-3-Cl,4-F5.16Cl 5.17 Cl H F-C6H4-4-SCH3 HF-C6H4-4-Cl5.18Cl HF-C6H4-4-F5.19Cl 5.20 Cl H F-C6H4-4-SCF3 5.21 F CH3 H-C6H4-4-CF3 5.22 F CH3 H-C6H4-4-OCF3 5.23 F CH3 H-C6H43-3, 4-CI2 5.24 F CH3 H-C6H4-3-CI 5.25 F CH3 H-C6H3-3-CI, 4-F CH3H-C6H4-4-SCH35.16F 5.27 F CH3 H-C6H4-4-CI CH3H-C6H4-4-F5.28F CH3H-C6H4-4-SCF35.29F HCl-C6H4-4-CF35.30F HCl-C6H4-4-OCF35.31F HCl-C6H43-3,4-Cl25.32F HCl-C6H4-3-Cl5.33F 5.34 F H Cl-C6H3-3-CI, 4-F HCl-C6H4-4-SCH35.35F HCl-C6H4-4-Cl5.36F HCl-C6H4-4-F5.37F HCl-C6H4-4-SCF35.38F 5.39 CH3 H F-C6H4-4-CF3 5.40 CH3 H F-C6H4-4-OCF3 HF-C6H43-3,4-Cl25.41CH3 HF-C6H4-3-Cl5.42CH3 HF-C6H3-3-Cl,4-F5.43CH3 HF-C6H4-4-SCH35.44CH3 HF-C6H4-4-Cl5.45CH3 5.46 CH3 H F-C6H4-4-F HF-C6H4-4-SCF35.47CH3 OCH3H-C6H4-4-CF35.48OCH3 No. Xi Xz Xa Rq Phys. data 5.49 OCH3 OCH3 H-C6H4-4-OCF3 5.50 OCH3 OCH3 H-C6H43-3,4-CI2 5.51 OCH3 OCH3 H-C6H4-3-CI 5.52 OCH3 OCH3 H -C6H5-3-Cl, 4-F 5.53 OCH3 OCH3 H-C6H4-4-SCH3 5.54 OCH3 OCH3 H-C6H4-4-CI 5.55 OCH3 OCH3 H -C6H4-4-F 5.56 OCH3 OCH3 H -C6H4-4-SCF3 2. Formulation Examples 2.1. Emulsifiable concentrates a) b) c) a compound of Tables 2 to 4 25 % 40 % 50 % calcium dodecylbenzenesulfonate 5 % 8 % 6 % castor oil polyethylene glycol ether (36 mol of ethylene oxide) 5 % tributylphenol polyethylene glycol ether (30 mol of ethylene oxide)-12 % 4 % 15%20%cyclohexanone- xylene mixture 65% 25% 20% Emulsions of any desired concentration can be prepared from such concentrates by dilution with water.

2.2. Emulsifiable concentrates a) b) c) ofTables2to410%8%60%acompound octylphenol polyethylene glycol ether (4-5 mol of ethylene oxide) 3 % 3 % 2 % calcium %4%4%3 castor oil polyethylene glycol ether (35 mol of ethylene oxide) 4 % 5 % 4 % cyclohexanone 40%15%% xylene mixture 50% 40% 15% Emulsions of any desired concentration can be prepared from such concentrates by dilution with water.

2.3. Suspension concentrate a compound of Tables 2 to 4 40 % ethylene glycol 10 % nonylphenol polyethylene glycol ether (15 mol of ethylene oxide) 6 % sodium lignosulfonate 10 % carboxymethylcellulose 1 % 37 % aqueous formaldehyde solution 0.2 % silicone oil in the form of a 75 % aqueous mulsion 0.8 % water 32 % The finely ground active ingredient is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired concentration can be obtained by dilution with water.

2.4. Powdermixtures dispersible inwater a) b) c) a compound of Tables 2 to 4 25 % 50 % 75 % sodium lignosulfonate 5 % 5 %- oleic acid 3 %-5 % sodium diisobutyinaphthalenesulfonate-6% 10% octylphenol polyethylene glycol ether (7-8 mol of ethylene oxide)-2 % highly dispersed silicic acid 5% 10% 10% kaolin 62% 27% The active ingredient is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording wettable powders which can be diluted with water to give suspensions of any desired concentration.

2.5. Dusts a) b) a compound of Tables 2 to 4 2 % 5 % highly dispersed silicic acid 1 % 5 % talcum 97 % kaolin-90 % Ready-for-use dusts are obtained by intimately mixing the carriers with the active ingredient and grinding the mixture.

2.6. Granules a) b) a compound of Tables 2 to 4 5 % 10 % kaolin 94 % highly dispersed silicic acid 1 %- attapulgite-90 % The active ingredient is dissolved in methylene chloride and the solution is sprayed onto the carrier, and the solvent is subsequently evaporated in vacuo. Such granules can be mixed with animal feed.

2.7. Granules a compound of Tables 2 to 4 10 % sodium lignosulfonate 2 % carboxymethylcellulose 1 % kaolin 87 % The active ingredient is mixed and ground with the adjuvants, and the mixture is moistened with water. The mixture is extruded and then dried in a stream of air.

2.8. Granules a compound of Tables 2 to 4 3 % polyethylene glycol (MW 200) 3 % kaolin 94 % (MW = molecular weight) The finely ground active ingredient is uniformly applied, in a mixer, to the kaolin moistened with polyethylene glycol. Non-dusty coated granules are obtained in this manner.

2.9. Tablets Constituents (for 1000 tablets): a compound of Tables 2 to 4 25.0 g lactose 100.7 g wheat starch 7.5 g polyethylene glycol 6000 5.0 g talcum 5.0 g magnesium stearate 1.8 g demineralised water q. s.

All the solid ingredients are first forced through a sieve of 0.6 mm mesh size. Then the active ingredient, the lactose, the talcum and half the starch are mixed together. The other half of the starch is suspended in 40 ml of water and the suspension is added to a boiling solution of the polyethylene glycol in 100 ml of water. The resulting starch paste is added to the main batch and the mixture is granulated, if necessary with the addition of water. The granules are dried overnight at 35°, forced through a sieve of 1.2 mm mesh size, mixed with the magnesium stearate and compressed to form tablets which have a mesh size of about 6 mm and which are concave on both sides.

2.10. Iniectable formulations A. Oily vehicle (slow release) a compound of Tables 2 to 4 0.1-1.0 g groundnut oil ad 100 ml a compound of Tables 2 to 4 0.1-1.0 g sesame oil ad 100 ml The active ingredient is dissolved in a portion of the oil with stirring and optionally with gentle heating, and after cooling the solution is made up to the desired volume and sterile-filtered through a suitable 0.22 mm membrane filter.

B. Water-miscible solvent (medium rate of release) a compound of Tables 2 to 4 0.1-1.0 g 4-hydroxymethyl-1,3-dioxolane (glycerol formal) 40 g 1,2-propanediol ad 100 ml a compound of Tables 2 to 4 0.1-1.0 g glycerol dimethyl ketal 40 g 1,2-propanediol ad 100 ml The active ingredient is dissolved in a portion of the solvent with stirring, and the solution is made up to the desired volume and sterile-filtered through a suitable 0.22 mm membrane filter.

C. Aqueous solubilisate (rapid release) a compound of Tables 2 to 4 0.1-1.0 g polyethoxylated castor oil (40 ethylene oxide units) 10 g 1,2-propanediol 20 g benzyl alcohol 1 g aqua ad inject. ad 100 ml a compound of Tables 2 to 4 0.1-1.0 g polyethoxylated sorbitan monooleate (20 ethylene oxide units) 8 g 4-hydroxymethyl-1,3-dioxolane (glycerol formal) 20 g benzyl alcohol 1 g aqua ad inject. ad 100 ml Preparation: The active ingredient is dissolved in the solvents and the surfactant, and the solution is made up to the desired volume with water. Sterile-filtration is then carried out through a suitable membrane filter of 0.22 mm pore diameter.

The aqueous systems can be used in a preferred manner also for oral and/or intraruminal administration.

2.11. Pour on A. a compound of Tables 2 to 4 10% epoxidised soybean oil 5% oleyl alcohol 85% B. a compound of Tables 2 to 4 20% pyrrolidin-2-one 15% isopropyl myristate 65% It is also possible to add to the described compositions further biologically active substances or additives that have neutral behaviour towards the compounds of formula (I) and have no adverse effect on the host animal to be treated, and also mineral salts or vitamins.

3. Bioloqical Examples A. Insecticidal action 3.1. 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 formula (I) exhibit good activity in this test.

3.2. Action against Diabrotica balteata Maize seedlings are sprayed with an aqueous mulsion spray mixture comprising 100 ppm of active ingredient and, after the spray-coating has dried, 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 formula (I) exhibit good activity in this test. For example, especially compounds 2.13 and 2.17 bring about a more than 80% reduction in the pest population.

3.3. Action against Heliothis virescens Young soybean plants are sprayed with an aqueous mulsion spray mixture comprising 100 ppm of active ingredient and, after the spray-coating has dried, 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 formula (I) exhibit good activity in this test. For example, especially compounds 2.13,2.17 ad 2.27 bring about a more than 80% reduction in the pest population.

3.4. Action against Spodoptera littorals Young soybean plants are sprayed with an aqueous mulsion spray mixture comprising 100 ppm of active ingredient and, after the spray-coating has dried, 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 formula (I) and (VIl) exhibit good activity in this test. For example, especially compounds 32,2.47,2.49 and 2.54 bring about a more than 80% reduction in the pest population.

3.5. Action against Nilaparvata lugens Rice plants are treated with an aqueous mulsion 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 formula (I) exhibit good activity in this test.

3.6. Action against Crocidolomia binotalis Young cabbage plants are sprayed with an aqueous mulsion spray mixture comprising 400 ppm of active ingredient. After the spray-coating has dried, the cabbage plants are populated with 10 Crocidolomia binotalis caterpillars in the third stage and placed in a plastics container. The evaluation is carried out 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 formula (I) exhibit good activity in this test.

3.7. Action against Anthonomus qrandis Young cotton plants are sprayed with an aqueous mulsion spray mixture comprising 400 ppm of active ingredient. After the spray-coating has dried, the cotton plants are populated with 10 Anthonomus grandis adults and placed in a plastics container. The evaluation is carried out 3 days later. The percentage reduction in population and the percentage reduction in feeding damage (% activity) are determined by comparing the number of dead weevils and the feeding damage on the treated plants with that on untreated plants.

Compounds of formula (I) exhibit good activity in this test.

3.8. Action against Aonidiella aurantii Potato tubers are populated with crawlers of Aonidiella aurantii. After about 2 weeks the potatoes are immersed in an aqueous mulsion or suspension spray mixture comprising 400 ppm of active ingredient. When the tubers have dried they are incubated in a plastics container. For evaluation, 10 to 12 weeks later the survival rate of the crawlers of the first subsequent generation of the treated population is compared with that of untreated controls.

Compounds of formula (I) exhibit good activity in this test.

3.9. Action against Bemisia tabaci Dwarf bean plants are placed in gauze cages and populated with adults of Bemisia tabaci.

After oviposition has taken place, all adults are removed. 10 days later the plants and the nymphs located thereon are sprayed with an aqueous mulsion spray mixture comprising 400 ppm of active ingredient. After a further 14 days, the percentage of eggs that have hatched is evaluated in comparison with untreated controls.

Compounds of formula (I) exhibit good activity in this test.

B. Acaricidal action 3.10. Action against Tetranvchus urticae Young bean plants are populated with a mixed population of Tetranychus urticae and sprayed 1 day later with an aqueous mulsion spray mixture comprising 100 ppm of active ingredient, incubated for 6 days at 25°C and then 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.

Compounds of formula (I) exhibit good activity in this test. For example, especially com- pounds 27,2.47,2.49 and 2.54 bring about a more than 80% reduction in the pest population.

3.11. Action against Panonvchus ulmi (OP and carb. resistant) Apple seedlings are populated with adult females of Panonychus ulmi. After seven days the infested plants are sprayed to drip point with an aqueous mulsion spray mixture comprising 400 ppm of the test compound and are cultivated in a greenhouse. The evaluation is carried out after 14 days. The percentage reduction in population (% activity) is determined by comparing the number of dead spider mites on the treated plants with that on untreated plants.

Compounds of formula (1) exhibit good activity in this test.

C. Ectoparasiticidal action 3.12. Control of adult fleas in cats bv means of pour-on application In order to determine the effectiveness of the test compounds against fully grown fleas, four groups each of two cats are used. Each cat is infested with 100 cat fleas [Ctenocephalides felis (Bouche)] and treated with 20 mg of active ingredient per kg body weight. The treatment is effected by applying the formulation to a locally defined area on the back of the cat's neck.

One group is infested with fleas but is treated only with a placebo, that is to say a formulation without active ingredient, and serves as control. Another group is treated with nitenpyram as comparison substance; the two remaining groups are treated with the test compounds.

Evaluation is carried out in each case by combing surviving fleas out of the animal's coat, counting them and comparing the number counted with the number of fleas in the control group and in the group treated with nitenpyram. The procedure in detail is as follows: each cat is infested with 100 fleas immediately after treatment on day 0. On day +1, each animal is combed and the number of surviving fleas is determined; the surviving fleas are then replace on the same cat and after 24 hours the combing and evaluation are repeated. The fleas still surviving after those 24 hours are not returned to the cat. The described procedure is then repeated on days +3, +7, +9, +14, +21, +28, +35, +42 and +49 and in this way the effectiveness and duration of action are determined. On every day on which surviving fleas are combed out, a blood sample of about 2.7 ml is taken from each cat-with the exception of the control group-and the content of active ingredient is measured. The effectiveness is determined in accordance with the following formula: number of living fleas minus number of living fleas per control animal per test animal % effectiveness =-* 100 number of living fleas per control animal It is shown that the compounds of formula (I) according to the invention achieve excellent long-ter action in comparison with nitenpyram.

In dogs the test proceeds in an entirely analogous manner. Similar effects are also observe when the substances are administered not in the form of a pour-on but in the form of an injection solution.

3.13. Control of adult fleas in cats by means of subcutaneous iniection In order to determine the effectiveness of the test compounds against fully grown fleas, four groups each of two cats aged from 1.5 to 4 years are used. Each cat is infested with 100 cat fleas [Ctenocephalides felis (Bouche)] and treated with 20 mg of active ingredient per kg body weight. The treatment is effected by subcutaneous injection of a solution of the active ingredient behind the left shoulder blade. One group is infested with fleas but is treated only with a placebo, that is to say a formulation without active ingredient, and serves as control.

Another group is treated with nitenpyram as comparison substance; the two remaining groups are treated with the test compounds. The evaluation is in each case carried out analogously to the preceding Example.

It is shown that after subcutaneous injection the compounds of formula (I) according to the invention achieve excellent long-term action in comparison with nitenpyram.

The analogous test with dogs gives comparable results.