MXPA00007185A - Organic nitrile derivatives and their use as pesticides - Google Patents

Abstract

Compounds of formula (I), wherein:A1 and A2 each represent independently of one other an aryl or a heteroaryl radical;and A1 where appropriate is substituted with substituent (R3a)n1 and A2 where appropriate with substituent (R3b)n2;n1 and n2 are independently of one another 0, 1, 2, 3 or 4;and either R3a and R3b independently of one another are for example halogen, C1-C6alkyl, C2-C4alkinyl, halogen-C1-C6alkyl, halogen-C2-C4alkinyl, C1-C6alkoxy, halogen-C1-C6alkoxy, C2-C6alkenyloxy, C2-C6alkinyloxy or halogen-C2-C6alkenyloxy;and R2 is R2a;R2a is for example -C1-C6alkyl-NR11R12, -COC9-C20alkyl, -C1-C6alkyl-O-C1-C6alkyl-O-C1-C6alkyl or -CH2O(C=O)C1-C6alkyl;or, at least one of the radicals R3a or R3b is -CR5=CR5R14, -NR11R12, -C(=O)CN, -C(=O)C(=O)O-C1-C6alkyl, -CR7=NOR10, or a five or six-membered heteroaryl ring bonded by a carbon atom;R2 is R2a or R2b, wherein R2a is as defined hereinbefore;and R2b is for example hydrogen, -OH, C1-C6alkyl or C1-C6alkoxy;R14 is for example hydrogen, halogen, C1-C6alkyl or halogen-C1-C6alkyl;X is O or S;p is 0, 1 or 2;R5 is independently H or C1-C8alkyl;R6 is for example independently H, C1-C8alkyl or C3-C6cycloalkyl;R7 is for example H, C1-C8alkyl, C2-C8alkenyl or halogen-C1-C8alkyl;R8 is for example C1-C8alkyl, C1-C8alkenyl or halogen-C1-C8alkyl;R9 is C1-C6alkyl, halogen-C1-C4alkyl or aryl;R10 is H, C1-C6alkyl, C3-C6cycloalkyl, phenyl or benzyl;R11 and R12 for example are independently of one another H, C1-C6alkyl or phenyl;and where applicable the possible E/Z isomers, E/Z isomer mixtures and/or tautomers thereof, in free form or in agrochemically acceptable form, can be used as agrochemical active ingredients and may be prepared in a known manner.

Description

ORGANIC NITRIL DERIVATIVES AND THEIR USE AS PESTICIDES The invention relates to a compound of the formula: wherein: Ax and A2 are independent of each other, and in each case represent a monocyclic or bicyclic aryl or heteroaryl radical, and each heteroaryl radical independently of the other has from 1 to and including 4 heteroatoms selected from the group consisting of in N, O, and S; and A-L is substituted where appropriate with a substituent (R3a) or 'Y ^ 2 where appropriate, with a substituent (R3b) n2; nx and n2 are independently of each other, 1, 2, 3, or 4, depending on the possibilities of substitution in the ring system x and Aj; and any of: (A) R3a and R3b, independently of one another, are hydrogen, halogen, alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkenyl of 2 to 4 carbon atoms, alkynyl of 2 to 4 carbon atoms, haloalkenyl of 2 to 4 carbon atoms, haloalkynyl of 2 to 4 carbon atoms, alkoxy of 1 to 6 carbon atoms, haloalkoxy of 1 to 6 carbon atoms, alkenyloxy of 2 to 6 carbon atoms, alkynyloxy with 2 to 6 carbon atoms, haloalkenyloxy with 2 to 6 carbon atoms, haloalkynyloxy with 2 to 6 carbon atoms, -OH, -SF5, -CHO, --C (= 0) -alkyl of 1 to 6 carbon atoms, -C. { = 0) -haloalkyl of 1 to 6 carbon atoms, -C (= 0) -O-alkyl of 1 to 6 carbon atoms, -C (= 0) -O-haloalkyl of 1 to 6 carbon atoms, - 0-C (= 0) N (R6) 2 (wherein both substituents Re are independent of each other), -CN, -N02 / -S (= 0) 2N (R6) 2 (wherein both substituents R6 are independent one of the other), -S (= 0) p-alkyl of 1 to 6 carbon atoms, -S (= 0) p-haloalkyl of 1 to 6 carbon atoms, -O- 5 (= 0) p-alkyl from 1 to 6 carbon atoms, -0-S (= 0) phaloalkyl of 1 to 6 carbon atoms, phenyl, benzyl, phenoxyl, or benzyloxy, wherein each of the phenyl, benzyl radicals, phenoxy, or benzyloxy is unsubstituted or substituted on the aromatic ring independently from each other, from 1 to 5 times, with substituents selected from the group consisting of halogen, cyano, N02, alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, and haloalkoxy of 1 to 6 carbon atoms; and R2 is R2a. or (B) R3a and R3b, independently of one another, are as defined in (A), and at least one of the radicals R3a or R3b is -CR5 = CRSR14, -NR ^ R ^, --C (= 0 ) CN, -C (= 0) C (= 0) O-alkyl of 1 to 6 carbon atoms, -CR15 = NOR10 or a 5 or 6 membered heteroaryl ring, wherein the heteroaryl ring is substituted, wherever appropriate, depending on the possibilities of substitution in the ring, with 1 to 3 substituents selected from the group consisting of halogen, alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 4 carbon atoms, N02, and CN; and R2 is R2a or R2b; or (C) R3a has one of the meanings defined hereinbefore in (A) or (B); R3b is hydrogen, halogen, alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkenyl of 2 to 4 carbon atoms, alkynyl of 2 to 4 carbon atoms, haloalkenyl of 2 to 4 carbon atoms , haloalkynyl of 2 to 4 carbon atoms, alkoxy of 1 to 6 carbon atoms, haloalkoxy of 1 to 6 carbon atoms, alkenyloxy of 2 to 6 carbon atoms, alkynyloxy of 2 to 6 carbon atoms, haloalkenyloxy of 2 to 6 carbon atoms, haloalkynyloxyl of 2 to 6 carbon atoms, -OH, -SF 5 -CHO, -C (= 0) -alkyl of 1 to 6 carbon atoms, -C (= 0) -haloalkyl of 1 to 6 carbon atoms, -C (= 0) -O-alkyl of 1 to 6 carbon atoms, -C (= 0) -O-haloalkyl of 1 to 6 carbon atoms, -OC (= 0) N (R6 ) 2 (wherein the two substituents R6 are independent of each other), -CN, -N02, phenyl, benzyl, phenoxy, or benzyloxy, wherein each of the phenyl, benzyl, phenoxy, or benzyloxy radicals is unsubstituted or substituted in The aromatic ring, independently of each other, is 5 times, with substituents selected from the group consisting of halogen, cyano, N02, alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, and haloalkoxy of 1 to 6 carbon atoms; -S (O) p-alkyl of 1 to 6 carbon atoms in the 4-position, or -S (= 0) p-haloalkyl of 1 to 6 carbon atoms in the 4-position, with the proviso that one of the substituents R3b is -S (= 0) p-alkyl of 1 to 6 carbon atoms or S (= 0) p-haloalkyl of 1 to 6 carbon atoms; and R2 is R2a or R2b; and in groups (A), (B) and (C), where appropriate, R 2a is alkyl of 1 to 6 carbon atoms-NR 1: LR 12, -C (= X) -R 7a, -CO-alkyl 9 at 20 carbon atoms, -CH20 (C = 0) -alkyl of 1 to 6 carbon atoms, -alkyl of 1 to 6 carbon atoms -O-alkyl of 1 to 6 carbon atoms -O-alkyl of 1 to 6 carbon atoms, -CH20 (C = 0) alkenyl of 2 to 6 carbon atoms, -CH20 (C = 0) alkynyl of 2 to 6 carbon atoms, -C (= S) O-alkenyl of 2 to 6 carbon atoms, -C (= S) O-alkynyl of 2 to 6 carbon atoms, -C (= S) S-alkyl of 1 to 6 carbon atoms, -C (= S) S-alkenyl of 2 to 6 carbon atoms, -C (= S) S-alkynyl of 2 to 6 carbon atoms, -C (= 0) S-alkyl of 1 to 6 carbon atoms, -C (= 0) S-alkenyl of 2 to 6 carbon atoms, -C (= 0) S-alkynyl of 2 to 6 carbon atoms, -C (= S) NR11R12, -C (= O) NR10OR13, -CH20-alkenyl of 2 to 6 carbon atoms , -CH20-alkynyl of 2 to 6 carbon atoms, -CH20-haloalkenyl of 2 to 6 carbon atoms, or -CH20-haloalquin ilo of 2 to 6 carbon atoms; R2b is hydrogen, -OH, alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, alkenyl of 3 to 6 carbon atoms, alkynyl of 3 to 6 carbon atoms carbon, haloalkyl of 1 to 6 carbon atoms, haloalkenyl of 3 to 6 carbon atoms, haloalkynyl of 3 to 6 carbon atoms, benzyl, or benzoyl, wherein the benzyl or benzoyl radical is substituted on the aromatic ring, independently one of the other, from 1 to 3 times, by substituents selected from the group consisting of halogen, -CN, N02, alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, and haloalkoxy of 1 to 6 carbon atoms; C 1 -C 6 alkoxy-C 1-6 -alkyl, C 1-6 -cyanoalkyl, -C (= X) -R7a, -C (= X) -Rh, -OC (= 0) ) -R7a, -C (= 0) -C (= 0) -R7a, -OC (= 0) -R7b, -C (= 0) -C (= 0) -R7b, S (= 0) pN ( R6) 2 (wherein the two substituents R6 are independent of one another); cyano, -alkyl of 1 to 6 carbon atoms-N (R5) -C (= 0) -R8, -alkyl of 1 to 6 carbon atoms-SC (= S) -R8, -alkyl of 1 to 6 atoms carbon-S (= 0) p-R9, -S (= 0) p-R9, or -CH2-N (R10) -SO2-R9; X is 0 or S; p is 0, 1, OR 2; Rs is independently H or alkyl of 1 to 8 carbon atoms; R6 is independently H, alkyl of 1 to 8 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, phenyl, or benzyl, wherein the phenyl or benzyl group is substituted on the aromatic ring, where appropriate, independently one of the another, 1 to 3 times, with substituents selected from the group consisting of halogen, -CN, N02, alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 4 carbon atoms, haloalkyl of 1 to 6 carbon atoms carbon, and haloalkoxy of 1 to 6 carbon atoms; or two alkyl radicals R6, together with the nitrogen atom to which they are bound, form a 5- to 7-membered ring, wherein a CH2 group, where appropriate, is substituted by a heteroatom selected from the group consisting of at 0 and S, or is substituted by NH, and wherein the 5- to 7-membered ring, where appropriate, is substituted once or twice with alkyl of 1 to 4 carbon atoms; R7a is alkoxy of 1 to 6 carbon atoms-alkyl of 1 to 6 carbon atoms, CH2CH2CF2C1, thioalkyl of 1 to 6 carbon atoms-alkyl of 1 to 6 carbon atoms, acyloxyalkyl of 1 to 6 carbon atoms, halocycloalkyl from 3 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms-alkyl of 1 to 6 carbon atoms, halocycloalkyl of 3 to 6 carbon atoms-alkyl of 1 to 6 carbon atoms, aryloxyalkyl of 1 to 6 atoms of carbon; or phenyl, benzyl, phenoxy, or aryloxyalkyl of 1 to 6 carbon atoms, which are substituted with 1 to 3 substituents selected from the group consisting of halogen, nitro, cyano, alkyl of 4 carbon atoms, haloalkyl of 1 to 4 carbon atoms, and haloalkoxy of 1 to 4 carbon atoms; R7b is H, alkyl of 1 to 8 carbon atoms, alkenyl of 2 to 8 carbon atoms, haloalkyl of 1 to 8 carbon atoms, haloalkenyl of 2 to 8 carbon atoms, alkoxy of 1 to 8 carbon atoms, haloalkoxy of 1 to 8 carbon atoms, cycloalkyl of 3 to 6 carbon atoms carbon, phenyl, benzyl, phenoxy, benzyloxy, or -N (R6) 2 (wherein both R6 are independent of each other); R8 is alkyl of 1 to 8 carbon atoms, alkoxy of 1 to 8 carbon atoms, haloalkyl of 1 to 8 carbon atoms, haloalkoxy of 1 to 8 carbon atoms, thioalkyl of 8 carbon atoms, phenyl, benzyl, or -N (R6) 2 (wherein the two R6 radicals are independent of each other); R9 is alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 4 carbon atoms, or aryl, which is unsubstituted or substituted 1 to 3 times, independently of one another, with substituents selected from the group consisting of alkyl from 1 to 6 carbon atoms, alkenyl of 2 to 4 carbon atoms, alkynyl of 2 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, halogen, cyano, haloalkyl of 1 to 4 carbon atoms, haloalkenyl of 2 to 4 carbon atoms, haloalkynyl of 2 to 4 carbon atoms, haloalkoxy of 1 to 4 carbon atoms, and nitro; R10 is H, alkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, phenyl, or benzyl, wherein the phenyl and benzyl radicals are unsubstituted or substituted in the aromatic ring 1 to 3 times, independently one of the other, with substituents selected from the group consisting of alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, halogen, cyano, haloalkyl of 1 to 4 carbon atoms, haloalkoxy of 1 to 4 carbon atoms, and nitro; R n and Ri 2 are, independently of one another, H, alkyl of 1 to 6 carbon atoms, phenyl, -CO-alkyl of 1 to 6 carbon atoms, -CO-haloalkyl of 1 to 6 carbon atoms, - CO-phenyl, or together they form a saturated or unsaturated ring of 5 or 6 members, where, if appropriate, one or more, especially one, of the CH- or CH2- groups is or is substituted by a heteroatom selected from of the group consisting of O, N, and S, and wherein the 5 or 6 membered ring, if appropriate, independently of one another, is substituted with 1 to 3 substituents selected from the group consisting of halogen, alkyl from 1 to 4 carbon atoms, haloalkyl of 1 to 4 carbon atoms, haloalkoxy of 1 to 4 carbon atoms, N02 / and CN; or the two substituents R1X and R12 together form a ring: q is 2 or 3; and R 13 is H, alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms; R 14 is hydrogen, alkyl of 1 to 6 carbon atoms, haloalkyl of 3 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, haloalkoxy of 1 to 6 carbon atoms, alkenyloxy of 2 to 6 carbon atoms, - CHO, -C (= 0) -alkyl of 1 to 6 carbon atoms, -C (= 0) -haloalkyl of 1 to 6 carbon atoms, -C (= 0) -O-alkyl of 1 to 6 carbon atoms carbon, -C (= 0) -O-haloalkyl of 1 to 6 carbon atoms, -CN, -N02, S (= 0) 2N (Rβ) 2 (wherein the two substituents R6 are independent of each other), -S (= 0) p-alkyl of 1 to 6 carbon atoms, -S (= 0) p-haloalkyl of 1 to 6 carbon atoms, -0-S (= 0) p-alkyl of 1 to 6 atoms of carbon, -0-S (= 0) phaloalkyl of 1 to 6 carbon atoms, phenyl, benzyl, or benzyloxy, wherein each of the substituents of phenyl, benzyl or benzyloxy is unsubstituted or substituted on the aromatic ring , independently from each other, from 1 to 5 times, with substitutes selected from the group consisting of halogen ene, cyano, N02, alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, and haloalkoxy of 1 to 6 carbon atoms; and R1S is hydrogen, alkyl of 1 to 6 carbon atoms, or haloalkyl of 1 to 6 carbon atoms; and if appropriate, to the possible E / Z isomers, mixture of E / Z isomers, and / or tautomers, in each case in free form or in the form of a salt, to a method for the preparation and use of these compounds , E / Z isomers and tautomers, pesticides, whose active ingredient is selected from these compounds, E / Z isomers and tautomers, and to a method for the preparation and use of these compositions, intermediates, in free form or in the form of a salt, for the preparation of these compounds, and where appropriate, their tautomers, in free form or in the form of a salt, and to a method for the preparation and use of these intermediates and their tautomers.

In the literature, certain phenyl hydrazone derivatives are proposed as active ingredients in pesticides. However, the biological properties of these known compounds are not completely satisfactory in the field of pest control, which is the reason why there is a need to produce additional compounds with pesticidal properties, especially for the control of insects and limbs. from the or-den Acariña; this problem is solved according to the invention, with the development of the present compounds of the formula la (I). Some compounds of the formula (I) comprise asymmetric carbon atoms, as a result of which the compounds may be present in an optically active form. Due to the presence of the double bond C = N, the compounds can occur in the isomeric forms E and Z. Atropisomers of the compounds may also be present. Formula (I) should encompass all of these possible isomeric forms and mixtures thereof, for example racemates or mixtures of E / Z isomers. The general terms used hereinbefore and hereinafter, have the following meanings, unless defined otherwise. The carbon-containing groups and compounds comprise, unless otherwise defined, in each case from 1 to 8 inclusive, preferably from 1 to 6 inclusive, more particularly from 1 to 4 inclusive, especially 1 or 2 carbon atoms. . Alkyl - as a group by itself and as a structural component of other groups and compounds, such as alkyl, alkoxy, or thioalkyl halide - in each case, with due consideration to the number of carbon atoms in the group or compound concerned is straight chain, ie methyl, ethyl, propyl, butyl, pentyl, or hexyl, or branched, for example isopropyl, isobutyl, secondary butyl, tertiary butyl, isopentyl, neopentyl, or isohexyl. Alkenyl - as a group by itself and as a structural component of other groups and compounds, such as alkenoxyl, alkenyl halide, or alkenoxyl halide -, in each case with due consideration to the number of carbon atoms in the The group or compound concerned is straight chain, for example vinyl, 1-methylvinyl, allyl, 1-butenyl, or 2-hexenyl, or branched, such as isopropenyl. Alkynyl - as a group by itself and as a structural component of other groups and compounds, such as alkynyl halide - in each case with due consideration to the number of carbon atoms in the group or compound concerned, is chain straight, for example propargyl, 2-butinyl, or 5-hexynyl, or branched, such as 2-ethynylpropyl or 2-propargylisopropyl. Cycloalkyl of 3 to 6 carbon atoms is cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl. Aryl is phenyl or naphthyl, especially phenyl. "Bicyclic heteroaryl" means a radical that can independently contain one or more heteroatoms in only one ring - such as, for example, in quinolinyl, quinoxalinyl, indo-linyl, benzothiophenyl, or benzofuranyl - as well as in both rings - such as, for example, , in pteridinyl or purinyl. Halogen - as a group by itself, and as a structural component of other groups and compounds, such as alkyl halide, alkenyl halide, and alkynyl halide - is fluorine, chlorine, bromine, or iodine, especially fluorine, chlorine, or bromine, more especially fluorine or chlorine, and very particularly chlorine. Groups and compounds substituted by carbon-containing halogen, such as alkyl halide, alkenyl halide, or alkynyl halide, may be partially halogenated or perhalogenated, wherein, in the case of repeated halogenation, the halogen substituents may be same or different. Examples of alkyl halide - as a group by itself and as a structural component of other groups and compounds, such as alkenyl halide - are methyl substituted 1 to 3 times by fluorine, chlorine, and / or bromine, such as CF2 or CF3; ethyl substituted 1 to 5 times by fluorine, chlorine, and / or bromine, such as CH2CF3, CF2CF3, CF2CC13 CF2CHC12, CF2CHF2, CF2CFC12, CF2CHBr2, CF2CHCIF, CF2CHBrF or CCIFCHCIF; propyl or isopropyl substituted 1 to 7 times by fluorine, chlorine, and / or bromine, such as CH2CHBrCH2Br, CF2CHFCF3, CH2CF2CF3 or CH (CF3) 2; and butyl or one of its isomers, substituted 1 to 9 times by fluorine, chlorine, and / or bromine, such as CF (CF3) CHFCF3 or CH2 (CF2) 2CF3. Alkenyl halide is, for example, CH2CH = CHC1, CH2CH = CC12, CH2CF = CF2 or CH2CH = CHCH2B. Alkynyl halide is, for example, CH2C = CF, CH2C = CCH2C1 or CF2CF2C = CCH2F. Some compounds of the formula (I), as is familiar to those skilled in the art, can be presented as tautomers, especially if R2 is H. According to the above, any reference to the compounds of the formula (I) previously in the present and subsequently in the present, it also includes its corresponding tautomers, even when the latter are not specifically mentioned in each case. The compounds of the formula (I) which show at least one basic center can form, for example, acid addition salts. These are formed, for example, with strong inorganic acids, such as mineral acids, for example perchloric acid, sulfuric acid, nitric acid, nitrous acid, a phosphoric acid, or a hydrogen halide, with strong organic carboxylic acids, such as C 1 -C 4 -carboxylic acids substituted, if appropriate, by halogen, for example, acetic acid, such as unsaturated dicarboxylic acids, if appropriate, for example oxalic, malonic, succinic, maleic, fumaric, or phthalic acid , such as hydroxycarboxylic acids, for example ascorbic acid, lactic acid, malic acid, tartaric acid, or citric acid, or benzoic acid, or with organic sulphonic acids, usually substituted alkanesulfonic acids of 1 to 4 carbon atoms or arylsulfonic acids, where appropriate, for example , by halogen, for example methanesulfonic or p-toluenesulfonic acid. In a broader sense, the compounds of the formula (I) with at least one acid group can form salts with bases. Salts with suitable bases are, for example, metal salts, usually alkali metal or alkaline earth metal salts, for example 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, for example ethyl-, diethyl-, triethyl-, or dimethyl-propylamine, or mono-, di-, or tri-hydroxy-lower alkylamine, for example mono-, di-, or triethanolamine. When appropriate, the corresponding internal salts can also be formed. The compounds of the formula (I) in free form are hereinafter and hereinafter taken to imply also their corresponding salts, and when applicable, the salts are taken to mean also the free compounds of the formula (I) ). The same applies for the tautomeric derivatives of the compounds of the formula (I) and their salts. In each case, the free form is generally preferred. The following forms are preferred within the scope of this invention. (1) A compound of the formula (I), wherein Ax and A2 are, independently of one another, a substituent selected from from the group consisting of: especially phenyl, naphthyl, pyridyl, or thiadiazolyl, very especially phenyl or pyridyl, in particular phenyl; R3 corresponds to R3a and R3b of the formula (I); R3a and R3 are, independently of one another, halogen, - CN, N02, haloalkyl of 1 to 2 carbon atoms, alkoxy of 1 to 2 carbon atoms, or haloalkoxy of 1 to 2 carbon atoms, haloalkenoxy of 2 to 5 carbon atoms, - [haloalkynyloxy] of 2 to 5 carbon atoms; especially chlorine, -CN, CF3, or 0CF3; wherein, if m + n is greater than 1, the radicals R3a and Rab are independent of each other; R 4 is H, alkyl of 1 to 4 carbon atoms, phenyl, or benzyl; especially H and methyl; n is from 0 to 5, especially from 1 to 3, depending on the possibility of substitution in the ring system, and the values of n in A are independent of the values of n in A2; m is from 0 to 4, depending on the possibility of substitution in the ring system, and the values of m in i are independent of the values of m in A2. The sum of m + n is from 0 to 5; especially 1, 2, or 3; (2) A compound of the formula (I), wherein A2 corresponds to the substituents selected from the group consisting of furanyl, thienyl, R2 is R2a or R2b; (3) A compound of the formula (I), wherein Ai and A2 are phenyl; (4) A compound of the formula (I), wherein: R 2a is -alkyl of 1 to 6 carbon atoms-NRuR 12, -C (= X) -R- =, -CO-alkyl of 9 to 20 carbon atoms carbon, -alkyl of 1 carbon atoms-O-alkyl of 1 to 6 carbon atoms-O-alkyl of 1 to 6 carbon atoms, -CH20 (C = 0) -alkyl of 1 to 6 carbon atoms, -CH20 (C = 0) -alkenyl of 2 to 6 carbon atoms, -CH20 (C = 0) -alkynyl of 2 to 6 carbon atoms, -C (= S) 0-alkenyl of 2 to 6 carbon atoms , -C (= S) 0-alkynyl of 2 to 6 carbon atoms, -C (= S) S-alkyl of 1 to 6 carbon atoms, -C (= S) S-alkenyl of 2 to 6 carbon atoms carbon, -C (= S) S-alkynyl of 2 to 6 carbon atoms, -C (= 0) S-alkyl of 1 to 6 carbon atoms, -C (= 0) S-alkenyl of 2 to 6 ato -mos of carbon, -C (= 0) S-alkynyl of 2 to 6 carbon atoms, -C. { = S) NR11R12, -C (= O) NR10OR13-CH20-alkenyl of 2 to 6 carbon atoms, -CH20-alkynyl of 2 to 6 carbon atoms, -CH20-haloalkenyl of 2 to 6 carbon atoms, or - CH20-haloalkynyl of 2 to 6 carbon atoms; especially, R2a is -CHa-alkyl-NR ^ R ^, -CO-alkyl of 9 to 20 carbon atoms, -alkyl of 1 to 2 carbon atoms-O-alkyl of 1 to 2 carbon atoms-O-alkyl of 1 to 2 carbon atoms, -CH20 (C = 0) -alkyl of 1 to 2 carbon atoms, -CH20 (C = 0) -alkenyl of 2 to 4 carbon atoms, -CH2? (C = 0) -alkynyl of 2 to 4 carbon atoms, -C (= S) 0-alkenyl of 2 to 4 carbon atoms, -C (= S) O-alkynyl of 2 to 4 carbon atoms, C (= S) S -alkyl of 1 to 2 carbon atoms, -C (= S) S-alkenyl of 2 to 4 carbon atoms, -C (= S) S-alkynyl of 2 to 4 carbon atoms, -C (= 0) S-alkyl of 1 to 2 carbon atoms, -C (= 0) S-alkenyl of 2 to 4 carbon atoms, -C (= 0) S-alkynyl of 2 to 4 carbon atoms, thioalkyl of 1 to 4 carbon atoms-alkyl of 1 to 2 carbon atoms, -C (= S) NR11R12, -C (= O) NR10? R13, -CH20-alkenyl of 2 to 4 carbon atoms, -CH20-alkynyl of 2 to 4 carbon atoms, -CH20-haloalkenyl of 2 to 4 carbon atoms, or -CH20-haloalkynyl of 2 to 4 carbon atoms; in particular. R ^ is -CH2-alkyl-NR11R12, -CO-alkyl of 9 to 20 carbon atoms, -alkyl of 1 to 2 carbon atoms-O-alkyl of 1 to 2 carbon atoms-O-alkyl of 1 to 2 carbon atoms, -CH20 (C = 0) -alkyl of 1 to 2 carbon atoms, -Cl (= 0) S-alkyl of 1 to 2 carbon atoms, -CH20-alkenyl of 2 to 4 carbon atoms, or -CH20-alkynyl of 2 to 4 carbon atoms; in particular, R2a is -CON (OCH3) CH3, -C (0) NHCOCH3, -C0SC2Hs, -COSCH3 -CH2OC (0) C (CH3) 3 < -CH2OC2H4OCH3, -CH2OCH2CH = CH2, -CH2OCH2C = CH, COC10H21; (5) A compound of the formula (I), wherein: R 2b is hydrogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms-alkyl of 1 to 4 carbon atoms, -C (= X) -R7a, -C (= 0) -alkyl of 1 to 4 carbon atoms, -C (= 0) -haloalkenyl of 3 to 6 carbon atoms, -C (= 0) -cycloalkyl of 3 to 6 atoms of carbon, -C (= 0) -alkyl of 1 to 2 carbon atoms, -C (= 0) -C (= 0) -O-alkyl of 1 to 2 carbon atoms, -C (= 0) - C (= 0) -N (R6) 2, cyano, benzoyl, or benzyl, wherein the benzoyl or benzyl radical is substituted on the aromatic ring, if necessary, independently of one another, from 1 to 3 times, with a substituent selected from the group consisting of halogen, -CN, -N02, trifluoromethoxy, and trifluoromethyl; or -C (= 0) -N (R6) 2; and The two R6 substituents, independently of one another, are H, alkyl of 1 to 4 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, phenyl, or benzyl, wherein the phenyl group 0 benzyl, if necessary, independently of one another, is substituted on the aromatic ring once or twice, with substituents selected from the group consisting of halogen, -CH, alkyl of 1 to 4 carbon atoms, alkoxy 1 to 4 carbon atoms, haloalkyl of 1 to 2 carbon atoms, and haloalkoxy of 1 to 2 carbon atoms; or two R6 alkyl radicals together with the nitrogen atom with which they are attached, form a 5 or 6 membered ring, where, if necessary, a CH2 group is substituted by a 0 or by NH atom, and wherein the 5 or 6 membered ring is substituted, if necessary, with methyl; especially, ^ 2b is hydrogen, alkenyl of 1 to 3 carbon atoms, alkoxy of 1 to 2 carbon atoms-alkyl of 1 to 2 carbon atoms, -C (= 0) -alkyl of 1 to 2 carbon atoms carbon, -C (= 0) -fluoroalkenyl of 4 to 6 carbon atoms, -C (= 0) -cyclopropyl, -C (= 0) -O-alkyl of 1 to 2 carbon atoms, -C (= 0 ) -C (= 0) -O-alkyl of 1 to 2 carbon atoms, -C (= 0) -C (= 0) -N (R6) 2, cyano, benzyl, or o-nitrobenzyl; -C (= 0) -N (R6) 2; or -C (= 0) -C6H5, wherein the phenyl ring in the same manner is substituted 1 to 3 times with a substituent selected from the group consisting of halogen, N02, trifluoromethoxy, and trifluoromethyl; and the two radicals R6, independently of one another, are H, alkyl of 1 to 4 carbon atoms, cyclopropyl, phenyl, or benzyl, wherein the phenyl or benzyl group, if necessary, independently of one another, is substituted in the aromatic ring once or twice by substituents selected from the group consisting of chlorine, -CN, and OCF3; or two R6 alkyl radicals, together with the nitrogen atom with which they are attached, form a six-membered ring, and wherein a -CH2 group, when applicable, is substituted by 1 O atom or by? TCH3; (6) A compound of the formula (I), wherein Ai is a pyridyl radical; (7) A compound of the formula (I), wherein: (R3a) m, is Cl, Cl2, Cl3, - (CF3) 2, Cl-CF3, N02, -CN, Cl2-N02, -OCF3, - CF3, CI-CF3, CI-CF3, Cl2-OCF3, -CI2-F, Cl2Br, Cl-CF3-F, Cl-Br-CH3, - (CH3) 2-Br, Cl3-CF3 / Cl2-F-CF3 / F2-CF3-C1, Cl2-CN, C12-CF3, C12-SCF3, Cl2-0CF3, Cl2-02CF3, C12-S02CH3, Cl2-0CF2Br, C12-0CF2H, C12-C2F5, (N02) 2-CF3, (N02) 2-C1, C12-S02CH3 or Cl2-OS02CF3; especially, 2-Cl, 2,3-Cl 2, 2,4-Cl 2, 2,6-Cl 2, 2,4,6-Cl 3, 3,5- (CF 3) 2, 2-CI-4-CF 3, 2 -N02, 2-CN, 3-CN, 4-CN, 2, 6-Cl2-4-N02, 4-OCF3, 4-CF3, 3-CF3, 2-Cl-4-CF3, 2-Cl-4 -N02, 2, 6-Cl2-4-CF3, 2, 6-Cl2-4-0CF3, 2,6-Cl2-4-F, 2,6-Cl2-4-Br, 2-Cl-4-CF3-6-F, 2-Cl-4-Br-6-CH3, 2,6- (CH3 ) 2-4-Br, 2,3,6-Cl3-4-CF3, 2, 6-Cl2-3-F-4-CF3, 2, 3-F2-4-CF3-6-Cl, 2.6 -Cl2-4-CN, 2,4-Cl2-6-CF3, 2, 6-Cl2-4-SCF3, 2, 6-Cl2-4-S0CF3, 2,6-Cl2-4-S02CF3, 2, 6 -Cl2-4-S02CH3, 2, 6-Cl2-4-0CF2Br, 2,6-Cl2-4- 0CF2H, 2,6-Cl2-4-C2F5, 2, 6- (N02) 2-4-CF3, 2, 6- (N02) 2-4-Cl, 2,6-Cl2-4-0S02CH3, or 2,6-Cl2-4-OS02CF3; very especially, 2,3-Cl 2, 2,4-Cl 2, 2,6-Cl 2, 2,4,6-Cl 3, 3,5- (CF 3) 2, 2-Cl-4-CF 3, 2-CN, 3-CN, 4-CN, 2, 6-Cl2-4-N02, 4-OCF3, 4-CF3, 3-CF3, 2-C1-4-CF3, 2-Cl-4-N02, 2, 6- Cl2-4-CF3, 2, 6-Cl2-4-OCF3, 2,6-Cl2-4-F, 2,6-Cl2-3-F-4-CF3, 2,3-F2-4-CF3- 6-Cl, 2, 6-Cl2-4-CN, 2, 4-Cl2-6-CF3, 2,6-Cl2-4-SCF3, 2,6-Cl2-4-SOCF3 2, 6-Cl2-4 -S02CF3, 2, 6-Cl2-4-C2Fs, 2,6- (N02) 2-4-CF3, 2,6- (N02) 2-4-Cl, 2, 6-Cl2-4-0S02CH3, or 2,6-Cl2-4-OS02CF3; (8) A compound of the formula (I), wherein a (R ^) ^ is -S (= 0) p-alkyl of 1 to 6 carbon atoms in the 4-position, or -S (= 0) p-haloalkyl of 1 to 6 carbon atoms in the 4-position; especially -S (= 0) p-alkyl of 1 to 3 carbon atoms, or -S (= 0) p-haloalkyl of 1 to 3 carbon atoms; more specifically is -S (= 0) p-haloalkyl of 1 to 3 carbon atoms; and especially, where n2 is 1 and R3b is S0CF3, S0C2Fs, SOCHF2, S0CF2Br, S0CF2C1, SOCF2CF2Br, SOCF2CF2Cl, SCF3, SC2FS, SCHF2, SCF2Br, SCF2C1, SCF2CF2Br, SCF2CF2C1, S02CF3, S02C2F5, S02CHF2, S02CF2Br, S02CF2C1, S02CF2CF2Br, S02CF2CF2C1; (9) A compound of the formula (I), wherein: (R3b) n2 is -CN, Cl, Cl2, F, F2, Br, -N02, - (N02) 2, -N02-CF3, CF3, - (CF3) 2, -CN-CF3, CI-CF3, F-CN, -Cl-CN, -OCF3, -Cl-N02, -CH3-N02 / -0CH3-N02, -C6H5, -C6H4-F, - C6H4-C1, -C6H4-CF3, -CβH4-CF3, - C6H4-N02, C6H3- (CF3) 2, -C6H3-C12, -C6H3- (Cl-F), -F-CN, F-N02, Cl -N02, C1-N02, -CHO, SCF3, SOCF3, S02CF3 or -C (= 0) CF3; especially, 4-CN, 3-CN, 4-Cl, 3,4-Cl 2, 2,3-Cl 2, 3,5-Cl 2, 2,5-Cl 2, 3,5-F 2, 2,6-F 2, 4-Br, 2-F, 4-N02, 2-N02-4-CF3, 3-CF3, 4-CF3, 3,5- (CF3) 2, 2-CN-4-CF3, 2-Cl-4 -CF3, 2-F-4-CN, 3-C1-4-CN, 4-OCF3, 3- and OCF3, 4-Cl-3-N02, 2-Cl-4-N02, 3-CH3-4- N02, 3-OCH3-4-N02, 4-C6H5, 4-C6H4-4-F, 4-C6H4-4Cl, 4-C6H4-4-CF3, 4-C6H4-3-CF3, 4-C6H4-3- N02, 4-C6H3- (3,5-CF3) 2, 4-C6H3-2.4-Cl2, 4-C6H3-3, 4-Cl2, 4-C6H3-3, 5-Cl2, 4-CßH3- ( 3-C1-4-F), 2-F-4-CN, 2-F-4-N02, 2-Cl-4-N02, 4-Cl-3-N02, 4-CHO, 4-SCF3, 4 -SOCF3, 4-S02CF3 or 4-C (= 0) CF3; especially, '4-CN, 3-CN, 4-Cl, 3,4-Cl2, 2,3-Cl2 3,5-Cl2, 2,5-Cl2, 3,5-F2, 2,6-F2 , 2-F, 2-N02-4-CF3, 4-N02, 3-CF3, 4, CF3, 3,5- (CF3) 2, 2-CN-4-CF3, 2-Cl-4-CF3, 2-F-4-CN, 3-C1-4-CN, 4-OCF3, 3-OCF3, 4-Cl-3-N02, 2-Cl-4-N02, 3-CH3-4-N02, 3- OCH3-4-N02, 4-C6Hs, 2-F-4-CN, 2-F-4-N02, 2-Cl-4-N02, 4-Cl-3-N02, 4-CHO, 4-SCF3, 4-SOCF3, 4-S02CF3, or 4-C (= 0) CF3; (10) A compound of the formula (I), wherein R2b is hydrogen; (11) A compound of the formula (I), wherein nx is 1, 2, 3, or 4, preferably 2 or 3; (12) A compound of the formula (I), wherein n2 is 1 or 2, preferably 1; (13) A compound of the formula (I), wherein nx is 2, 3, or 4, and n2 is 1 or 2; (14) A compound of the formula (I), wherein: R n and Ri 2 are, independently of one another, H, alkyl of 1 to 2 carbon atoms, phenyl, -CO-alkyl of 1 to 2 carbon atoms, -CO-phenyl, or together they form a 5 or 6 membered ring, saturated or unsaturated, wherein one of the CH- or CH2- groups is applicable if it is substituted by a heteroatom selected from the group consisting of O, N , and S, and wherein the 5- or 6-membered ring, if applicable, is substituted with 1 or 2 substituents selected from the group consisting of alkyl of 1 to 2 carbon atoms, haloalkyl of 1 to 2 carbon atoms. carbon, N02, CN; or the two substituents Rxl and R12 together form a ring: and q is 2; especially, Rn and Ri2 are, independently of one another, H, alkyl of 1 to 2 carbon atoms, phenyl, -CO-alkyl of 1 to 2 carbon atoms, -CO-phenyl, most especially H, methyl, or ethyl . (15) A compound of the formula (I), wherein: at least one of R3a and / or R3b is / are -CR5 = CR5R14, and R14 is hydrogen, alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, -CHO, -C. { = 0) -alkyl of 1 to 6 carbon atoms, -C (= 0) -haloalkyl of 1 to 6 carbon atoms, -C (= 0) -O-alkyl of 1 to 6 carbon atoms, -C ( = 0) -O-haloalkyl of 1 to 6 carbon atoms, -CN, -N02, -S (= 0) 2N (R6) 2, (wherein the two substituents R6 are independent of each other), -S ( = 0) p-alkyl of 1 to 6 carbon atoms, phenyl, benzyl, or benzyloxy; and R5 is hydrogen or alkyl of 1 to 2 carbon atoms; especially one of R3a or R3b is -CR5 = CRSR14; R14 is hydrogen, alkyl of 1 to 2 carbon atoms, haloalkyl of 1 to 2 carbon atoms, phenyl, or benzyl; and R1S is methyl, or CF3; (16) A compound of the formula (I), wherein R 5 independently H, or alkyl of 1 to 2 carbon atoms; (17) A compound of the formula (I), wherein: n2 is 1, and (R3b) n2 is SCH3, SCF3, SC2H5, SC2F5, SOCH3, SOC2H5, SOC2F5, S02N (CH3) 2, S02N (C2H5) 2 , S02CH3, S02CF3, S02C2H5, 'S02C2F5, SOCF3, SOCHF2, SOCF2Br, S0CF2C1, SOCF2CF2Br, SOCF2CF2Cl, SCHF2, SCF2Br, SCF2C1, SCF2CF2Br, SCF2CF2C1, S02CHF2, S02CF2Br, S02CF2C1, S02CF2CF2Br or S02CF2CF2C1; in particular, SCF3 SC2F5, S0CF3, S0C2F5, S02CF3, or S02C2F5; and R2 is R2a or R2b, especially H, -CH2OC2H5, -COCH3-, -CH3, -CN, -CH2C = CH, -C2H5, -COOCH3 or -CON (CH3) OCH3. Within the scope of this invention, the compounds of the formula (I) listed in Tables 3 to 27 are particularly preferred, and, where applicable, the E / Z isomers and E / Z isomeric mixtures thereof. A further object of the invention is the method for preparing the compounds of the formula (I), and where appropriate, their E / Z isomers, E / Z isomeric mixtures, and / or tautomers thereof, in each case in the form free or in the form of a salt, which comprises any of: a) for the preparation of a compound of the formula (I), wherein the substituents ^ and Aj, are as defined hereinabove, and R2 is hydrogen, aa) the diazotization of a compound of the formula: AX-NH2 (III), wherein Ax is as defined hereinabove in formula (I), and ab) the reaction of the diazonium salt with a composed of the formula: CN W (IV), wherein Aj is as defined hereinabove in formula (I), and W is hydrogen or a removable group; or b) for the preparation of a compound of the formula: wherein Ax, A ^, and R2 are as defined hereinabove for R2a and R2b in the compounds of the formula (I), the reaction of a compound of the formula: where Al f. , and R 2 are as defined hereinabove for R 2a and R 2b in the compounds of the formula (I), and Hal is a halogen atom, preferably chlorine or bromine, especially chlorine, with a metal cyanide, preferably an alkali metal cyanide, especially with sodium cyanide; c) for the preparation of a compound of -Xa formula (I), wherein R2 is different from H, the reaction of a compound of the formula (I), wherein R2 is hydrogen, with a compound of the formula: R2 -Q (V), wherein R2 is as defined hereinabove for R2a and R2b in formula (I), and Q is a leaving group, preferably chlorine, bromine, or iodine, especially iodine, preferably rencia in the presence of a base; and in each case, if desired, the conversion of a compound of the formula (I) or an E / Z isomer or tautomer thereof, in free form or in the form of a salt, and which can be obtained by of the method, or by other means, to another compound of the formula (I) or an E / Z isomer or tautomer thereof, in free form or in the form of a salt, separating a mixture of E / Z isomers that can be obtained by means of the method or by other means, and the isolation of the desired isomer, and / or the conversion of the free compound of the formula (I) or an E / Z isomer or tautomer thereof, which can be obtained by of the method, or by other means, up to a salt, or the conversion of a salt, which can be obtained by the method or by other means, of a compound of the formula (I) or of an E / Z isomer or tautomer thereof, to the free compound of the formula (I) or an E / Z isomer or tautomer thereof, or to another salt. A further object of the invention is a method for the preparation of a compound: d) of the formula: wherein Ax, Aj, and R2 are as defined hereinabove for R2a and R2b in the compounds of the formula (I), and Hal is a halogen atom, and where applicable, the E / Z isomers and tautomers thereof, in free form or in the form of a salt, which comprises the reaction of a compound of the formula: wherein the radicals Ax and ^ and R2 have the same meaning as defined hereinabove in the formula (bundle) for R2a and R2b, with a halogenation agent, or e) of the formula: wherein R2 and the two radicals L and Aj have the same meaning as defined hereinabove for Alf A2, R2a, and R2b in the formula (I), and Hal is a halogen atom, preferably chlorine, which comprises the reaction of a compound of the formula: wherein R2 and the two radicals Ax and A2 have the same meaning as defined hereinbefore in the formula (Ilb), with N-bromosuccinimide or N-chlorosuccinimide, in the presence of a thioether, and in each case, if desired, the conversion of a compound of the formula (II) or an E / Z isomer or tautomer thereof in free form or in the form of a salt , and which can be obtained by means of the method or by other means, to another compound of the formula (II) or an E / Z isomer or tautomer thereof, in free form or in the form of a salt, the separation of a mixture of E / Z isomers obtainable by the method, or by other means, and the isolation of the desired isomer or, and / or the conversion of a free compound of the formula (II) or E / Z isomer or tautomer thereof, which can be obtained by means of the method or by other means, to a salt, or the conversion of a salt or the conversion of a salt, which can be obtained by means of the method or by other means, of a compound of the formula (II) or of an E / Z isomer or tautomer thereof, to the free compound of the formula ( II) or an E / Z isomer or tautomer thereof, or even another salt. The reactions described hereinafter and subsequently herein are carried out in a known manner, wherein the work can be carried out, depending on the requirements, with cooling, at room temperature, or with heating, for example on a scale of temperature from about 0 ° C to the boiling point of the reaction medium, preferably from about 20 ° C, to about + 120 ° C, especially from 60 ° C to 80 ° C, and if necessary, in a closed container, under pressure and in an inert gas atmosphere, for example under nitrogen or argon, and / or under anhydrous conditions. Reactions that are carried out at a normal pressure under nitrogen are preferred. The reaction components can be reacted with each other as they are, that is, without the addition of a solvent or diluent, for example in the melt. However, in most cases, it is convenient to add an inert solvent or diluent, or a mixture thereof. Particularly convenient reaction conditions are described in the examples. The isolation of the products takes place in accordance with the usual methods, for example by filtration, crystallization, distillation, or chromatography, or any suitable combination of these methods.

Variant a); aa) The diazotization takes place under conditions familiar to those skilled in the art, ie in the presence of strong inorganic acids, such as mineral acids, for example perchloric acid, sulfuric acid, nitric acid, nitrous acid, a phosphoric acid , or a hydrogen halide, usually in the presence of water, but also in pure sulfuric acid. Depending on the basicity of the aromatic amine, the reaction takes place on a temperature scale of about -10 ° C to about + 20 ° C, or if necessary, even at a higher temperature, for example 60 ° C to 80 ° C. The reaction time of preference is from about 1 to about 2 hours. The product is not normally isolated, but is further processed in the next reaction step. Especially preferred conditions for the reaction are described in Example H6 / a. ab) The reaction usually takes place in the presence of water, and preferably in the presence of an organic carboxylic acid, such as formic acid, chloroacetic acid, trifluoroacetic acid, cyanoacetic acid, oxalic, malonic, succinic, maleic, fumaric, or phthalic; the addition of acetic acid is especially preferred. A removable group W means an electrophilic group that can be easily removed under the prevailing reaction conditions. Especially suitable for this are -C (= 0) R or -0C (= 0) R, where R is H, alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, haloalkoxy of 1 to 4 carbon atoms, -CN, or organic sulfonates, such as alkane sulfonates of 1 to 4 carbon atoms or of aryl substituted, if necessary, for example by halogen, for example methane, trifluorometal, or p-toluenesulfonate. The reaction is conveniently carried out within a temperature range from about -10 ° C to about + 30 ° C, preferably from about 0 ° C, to about + 25 ° C. The reaction time of about 0.5 to about 8 hours, especially about 2 to about 4 hours, is preferred. Variant b): For the reaction, transition metal cyanides, such as CuCN, or Ni (CN) 2, as well as the alkaline earth and alkali metal cyanides are suitable; especially KCN and NaCN. Examples of the solvents or diluents are: aromatic, aliphatic, and alicyclic hydrocarbons, and halogenated hydrocarbons, such as benzene, toluene, xylene, mesitylene, tetralin, chlorobenzene, dichlorobenzene, bromobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform , tetrachloromethane, dichloroethane, trichloroethene, or tetrachloroethene, esters, such as ethyl acetate; ethers, such as diethyl ether, dipropyl ether, di-isopropyl ether, dibutyl ether, tertiary butyl methyl ether, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol dimethyl ether, dimethoxydieyl ether, tetrahydrofuran, or dioxane; ketones, such as acetone, methyl ethyl ketone, or methyl isobutyl ketone; alcohols, such as methanol, ethanol, propanol, isopropanol, butanol, ethylene glycol, or glycerol; diethylformamide, N, N-dimethylacetamide, N-amides, such as N, N-dimethylformamide, N, N-methylpyrrolidone, or hexamethylphosphoric triamide; nitriles, such as acetonitrile or propionitrile; and sulfoxides, such as dimethyl sulfoxy, or water. Alcohols and water, or alcohol / water mixtures are preferred. The reaction is conveniently carried out within a temperature range from about 0 ° C to about 80 ° C, preferably from about 20 ° C to about 30 ° C, in many cases on the scale between room temperature and reflux temperature of the reaction mixture. The reaction time of about 0.1 to about 24 hours, especially about 3 to about 5 hours, is preferred. In a preferred form of variant b), a compound of the formula (II) is reacted in an ethanol / water mixture with sodium cyanide at room temperature.

Variant c): Suitable leaving groups Q in the compounds of the formula (V) are, for example, hydroxyl, alkoxy of 1 to 8 carbon atoms, haloalkoxy of 1 to 8 carbon atoms, alkanoyloxy of 1 to 8 carbon atoms. carbon, mercapto, thioalkyl of 1 to 8 carbon atoms, halotioalkyl of 1 to 8 carbon atoms, alkanesulfonyloxy of 1 to 8 carbon atoms, haloxanesulfonyloxy of 1 to 8 carbon atoms, benzenesulfo-niloxyl, toluenesulfonyloxy, and halogen , preferably toluenesulfonyloxy, trifluoromethanesulfonyloxy, or halogen, especially halogen, in particular bromine or chlorine. Suitable bases for facilitating the reaction are, for example, hydroxides, hydrides, amides, alkanolates, acetates, carbonates, dialkylamides, or alkylsilylamides of alkali metals or alkaline earth metals, alkylamines, alkylenediamines, cycloalkylamines (N-alkylated where appropriate, and unsaturated where appropriate), basic heterocycles, ammonium hydroxides, and carbocyclic amines. Examples are: hydroxide, hydride, amide, methanolate, acetate, and sodium carbonate, terbutanolate, hydroxide, carbonate, potassium hydride, lithium diisopropylamide, potassium bis (trimethylsilyl) amide, calcium hydride, triethylamine, di-isopropylethylamine, triethylendiamine, cyclohexylamine, N-cyclohexyl-N, N-dimethylamine, N-diethylamine, N, N-diethylaniline, pyridine, 4- (N, N-dimethylamino) -pyridine, quinuclidine, N-methylmorpholine, benzyl trimethylammonium hydroxide, and 1,5-diazabicyclo [5.4.0] undec-5-ene (DBU). Preference is given to alkali metal and alkaline earth metal carbonates, alkylamines, and alkali metal or alkaline earth metal alkanolates. Examples of the solvents or diluents are: aromatic, aliphatic, and alicyclic hydrocarbons, usually benzene, toluene, xylene, mesitylene, tetralin, chlorobenzene, dichlorobenzene, bromobenzene, petroleum ether, hexane, cyclohexane; ethers, such as diethyl ether, dipropyl ether, diisopropyl ether, dibutyl ether, tertiary butyl methyl ether, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol dimethyl ether, dimethoxy di ethyl ether, tetrahydrofuran, or dioxane; esters, such as ethyl acetate and methyl acetate; and sulfoxides, such as dimethyl sulfoxide. Ethers, such as tertiary butyl methyl ether, tetrahydrofuran, or dioxane, and esters, such as ethyl acetate, are preferred. The reaction is conveniently carried out within a temperature range from about 0 ° C to about + 120 ° C, preferably from about '0 ° C to about + 80 ° C. The reaction time of from about 0.1 to about 24 hours, especially from about 0.5 to about 2 hours, is preferred.

Variant d): The reaction preferably takes place in the presence of an acid catalyst, for example in the presence of a carboxylic acid, such as formic acid, acetic acid, malonic acid, or oxalic acid, or also a sulphonic acid, such as alkanesulfonic acid of 1 to 4 carbon atoms or arylsulfonic substituted, if necessary, for example, by halogen, for example methane, trifluoromethane, or p-toluenesulfonic acid. Solvents that are suitable for the azeotropic removal of water are especially suitable. Examples of these solvents or diluents are: aromatic, aliphatic, and alicyclic hydrocarbons, and halogenated hydrocarbons, such as benzene, toluene, xylene, mesitylene, tetralin, chlorobenzene, dichlorobenzene, bromobenzene, petroleum ether, hexane, cyclohexane, dichloromethane , chloroform, tetrachloromethane, dichloroethane, trichloroethene, or tetrachloroethene; esters, such as ethyl acetate; ethers, such as dipropyl ether, diisopropyl ether, dibutyl ether, tertiary butyl methyl ether, di-methoxydiethylether; ketones, such as methyl isobutyl ketone; alcohols, such as ethanol, propanol, isopropanol, butanol, ethylene glycol, or glycerol. The reaction is conveniently carried out within a temperature range from about 60 ° C to about 180 ° C, preferably from 80 ° C to approximately 130 ° C, in many cases at the reflux temperature of the reaction medium. The preferred reaction time is from about 6 to about 72 hours, especially from about 12 to about 48 hours. In a preferred form of variant d), the reaction is carried out at 80 ° C to 140 ° C in an alcohol or in an aromatic hydrocarbon, in the presence of carboxylic acid of 1 to 4 carbon atoms.

Variant e): Preferred halogenation agents are Cl2, Br2, S0C12, S02C12, P0C13, PCI3, PC15 and C0C12. Examples of the solvents or diluents are: aromatic, aliphatic, and alicyclic hydrocarbons, and halogenated hydrocarbons, such as benzene, toluene, xylene, mesitylene, tetralin, chlorobenzene, dichlorobenzene, bromobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform , te-tracloromethane, dichloroethane, trichloroethene, or tetrachloroethene; esters, such as ethyl acetate; ethers, such as diethyl ether, dipropyl ether, di-isopropyl ether, dibutyl ether, tertiary butyl methyl ether, ethylene glycol dimethyl ether, dimethoxydieyl ether, tetrahydrofuran, or dioxane; ketones, such as acetone, methyl ethyl ketone, or methyl isobutyl ketone; amides, such as N, N-dimethylformamide, N, N-methylpyrrolidone, or hexamethylphosphoric acid triamide; nitriles, such as acetonitrile or propionitrile. The reaction is conveniently carried out within a temperature range from about 0 ° C to about 180 ° C, preferably from about 50 ° C to about 100 ° C, in many cases on the scale between room temperature and temperature reflux of the reaction mixture. The reaction time is not critical; a reaction time of from about 0.1 to about 24 hours, especially from about 3 to about 6 hours, is preferred. The compounds of formulas (I), (lia), (Ilb), and (VIII) may be present in the form of one of the possible isomers, or as a mixture thereof, depending, for example, on the number and of the absolute and relative configuration of the asymmetric carbon atoms as pure isomers, such as enantiomers and / or diastereomers or mixtures of isomers, such as mixtures of enantiomers, for example racemates; the invention relates both to the pure isomers and to all possible isomeric mixtures, and it is understood hereinbefore and hereinafter that it is so, even when the stereochemical details are not specifically mentioned in each case. Mixtures of diastereomers and mixtures of racemates of the compounds of formulas (I), (lia), (Ilb) and (VIII), which can be obtained as described in the method - depending on the starting materials and the selected working procedures - or by other means, due to the physicochemical differences of the constituents, can be separated in a known manner in the diastereomers or pure racemates, for example, by fractional crystallization, distillation, and / or chromatography . The resolution of the mixtures of enantiomers that can be obtained in a corresponding manner, such as racemates, can be achieved by known methods, for example, by recrystallization from an optically active solvent, by chromatography on chiral absorbents, for example chromatography of high-pressure liquids (HPLC) on acetyl-cellulose, through the use of suitable microorganisms, by dissociation with specific immobilized enzymes, through the formation of inclusion compounds, for example using chiral crown ether, where only complex with an enantiomer. According to the invention, apart from the isolation of the corresponding isomer mixtures, the generally known methods of diastereoselective or enantioselective synthesis can also be applied, to obtain pure diastereomers or enantiomers, for example by performing the method of the invention using educts with a correspondingly appropriate stereochemistry. It is convenient to isolate or synthesize the biologically most active isomer in each case, for example the enantiomer or the mixture of isomers, for example the mixture of enantiomers, if the individual components show differences in their biological effectiveness.

The compounds of the formulas (I), (lia), (IIb), and (VIII), can also be obtained in the form of their hydrates, and / or can also include other solvents used, for example, where necessary, for the crystallization of the compounds present in solid form. The invention relates to all forms of the method, according to which one starts from a compound that can be obtained as a primary material or an intermediate at any stage of the method, and perform all or some of the missing steps, or uses, or - especially under the reaction conditions - produces a starting material in the form of a derivative or a salt, and / or its racemate or enantiomer. In the method of the present invention, the starting materials and intermediates used are preferably those which lead to the compounds of the formula (I) described at the beginning as being especially useful. The invention relates in particular to the manufacturing processes described in Examples Hl, H2, H4, and H5. , The starting materials and intermediates used according to the invention for the preparation of the compounds of the formula (I), and in particular the compounds of the formulas (II), (III), (IV) and (VIII) ), which are new, and their use and methods for their preparation, in the same way form an object of the invention. The compounds of the formulas (lía), (Ilb), and (VIII), as well as the use thereof for the preparation of the compounds of the formula (I), represent a further object of the invention. The compounds of formulas (III) to (VI) and (IX) are known, or can be prepared according to known methods. A further object of the invention is a method for controlling pests using a compound of the formula (I), wherein Ax, j, and R2 have the same meaning as defined hereinabove for the formula (I). The compounds of the formula (I) according to the invention are active substances of preventive and / or curative merit, for use in the control of pests and offer a spectrum of very favorable biocidal activity, with favorable tolerability in warm-blooded animals, fish, and plants, even in low concentrations. The compositions according to the invention are active against all individual stages of development of the animal pests showing normal sensitivity, and also of those showing resistance, for example insects or members of the order Acariña.

The insecticidal, ovicidal, and / or acaricidal effect of the compositions of the invention can be manifested directly, that is, annihilating the pests either immediately or after some time has elapsed, for example, when the molting occurs, or their eggs , or indirectly, for example by reducing the number of eggs laid and / or the hatching rate, a good efficiency corresponding to a destruction index (mortality) of at least 50 to 60 percent. Animal pests include, for example: Members of the orders of Lepidoptera, Coleoptera, Orthoptera, Isoptera, Psocoptera, Anoplura, Malophagous, Tisa-noptera, Heteroptera, Homoptera, Hymenoptera, Diptera, Si-fonapteros, Tisanura, and Acariña; pest control of the genera and species described in European Patent Number EP-A-736, 252, and which are hereby incorporated by reference, is especially preferred. Pests of this type that occur in plants, especially in crops and ornamentals in agriculture, horticulture, and forestry, or in parts of plants, such as fruits, buds, leaves, stems, tubers, or roots, are they can control, that is to say, keep controlled or eradicated, using the active ingredients of the invention, this protection remaining for the parts of some plants whose growth does not occur until later. White crops within the scope of this application include especially cereals, such as wheat, barley, rye, oats, rice, corn, or sorghum; beet, such as sugar beet or fodder beet; fruit, for example grapefruit, fruit, and soft fruit, such as apples, pears, cirue-las, peaches, almonds, cherries, or berries, for example, freesas, raspberries, or blackberries; leguminous plants, such as beans, lentils, peas, or soybeans; oleaginous fruits, such as rapeseed, mustard, poppy, olives, sunflowers, coconut, castor oil plants, cocoa seeds, or caca-huates; cucumber plants, such as pumpkins, cucumbers, or melons; fibrous plants, such as cotton, flax, hemp, or jute, - citrus fruits, such as oranges, lemons, grapefruits, or tangerines; vegetables, such as spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, or paprika; lauraceae, such as avocado, canals, or camphor; and tobacco, nuts, coffee, aubergines, sugar cane, tea, pepper, vines, hops, banana plants, natural rubber plants, and ornamentals. The active ingredients of the invention are especially suitable for the control of insects and members of the order Acariña, in particular insects that feed on crops, and are harmful, such as larvae of Anthonomus granáis, Diabrotica balteata, Heliothis virescens, -Plutella xylostella and Spodoptera li ttoralis, and spider mites, such as Tetranychus spp., in cultivated cotton, fruit, corn, soybean, rapeseed, and vegetable plants. Other areas of indication for the active ingredients of the invention are the protection of stored products and stores, and of the material, and in the hygiene sector, in particular the protection of domestic animals and livestock against pests of this type. Accordingly, the invention also relates to pesticides comprising a compound of the formula (I), wherein Ax, 2, and R 2 have the same meaning as defined hereinabove for the formula (I), with the exception of l-phenylhydrazono-2-nitrilethylbenzene, such as emulsifiable concentrates, suspension concentrates, ready-to-spray or ready-to-dilute solutions, coatable pastes, diluted emulsions, sprayable powders, soluble powders, dispersible powders, wettable powders, powders dry, granulated, or encapsulated in polymeric substances (selected according to the intended objectives and prevailing circumstances), comprising at least one active ingredient of the invention. In these compositions, the active ingredient is used in pure form, the solid active ingredients in a specific particle size, or preferably together with - at least - one of the adjuvants conventionally used in the formulation art, such as extenders, for example solvents or solid vehicles, or surface activity compounds (surfactants). Suitable adjuvants, such as solvents, solid carriers, surface-active compounds, non-ionic surfactants, cationic surfactants, and anionic surfactants, in the compositions used according to the invention, are the same as those described in the European Patent Number EP-A-736,252 (CASE 20400), and which are included in the present object of the invention as reference. As a rule, the compositions comprise from 0.1 to 99 percent, especially from 0.1 to 95 percent active ingredient, and from 1 to 99.9 percent, especially from 5 to 99.9 percent of - at least - a solid or liquid adjuvant, wherein from 0 to 25 percent, especially from 0.1 to 20 percent of the composition, as a rule, can be a tensoac-tive (percent in each case means percent by weight). Although concentrated compositions for commercial articles tend to be preferred, the end consumer, as a rule, uses dilute compositions having substantially lower concentrations of active ingredient. Therefore, the preferred compositions are composed in particular as described in European Patent Number EP-A-736,252. The activity of the compositions of the invention can be substantially extended and adapted to the prevailing circumstances by the addition of other insecticidal, acaricidal, and / or fungicidal substances. Additional active ingredients are, for example, substances of the following classes: organophosphorus compounds, nitrophenols and derivatives, formamidine, urea, carbamates, pyrethroids, chlorinated hydrocarbons, and preparations of Bacillus thuringiensis. The compositions of the invention may also comprise other solid or liquid adjuvants, such as stabilizers, for example vegetable oils, epoxidized where appropriate (for example, coconut oil, rape seed oil, or epoxidized soybean oil), antifoaming agents, for example silicone oil, preservatives, viscosity modulators, binders and / or viscosifiers, and also fertilizers or other active ingredients to achieve specific effects, for example acaricides, bactericides, ne-matocides, mulusquicides, or selective herbicides. The compositions of the invention are prepared in a known manner, in the absence of adjuvants, for example, by grinding and / or screening a solid active ingredient or a mixture of active ingredients, for example up to a specific particle size, and in the presence of at least one adjuvant, for example, by intimate mixing and / or milling of the active ingredient or mixture of active ingredients with the adjuvants. These methods for preparing the compositions of the invention, and the use of the compounds of the formula (I) to prepare these compositions, in the same manner form an object of the invention. The methods of application for the compositions, that is, the methods for controlling pests of this type, such as spraying, atomizing, dusting, coating, coating, dispersing, or watering (selected according to the intended objectives and the prevailing circumstances), and the use of the compositions for controlling pests of this type are additional objects of the invention. Typical concentrations of the active ingredient are between 0.1 and 1000 ppm, preferably between 0.1 and 500 ppm. The application concentrations are generally from 1 to 2,000 grams of active ingredient (i.a.) per hectare (ha = approximately 2,471 acres), especially from 10 to 1000 grams of active ingredient per hectare., and preferably from 20 to 600 grams of active ingredient per hectare. A preferred method of application for crop protection is to apply the active ingredient to the foliage of the plants (application to the leaves), depending on the number of applications and the concentration of application of the intensity of infestation by the pest in question. However, the active ingredients can also penetrate the plant through the roots by means of the soil (systemic action), by impregnation of the plant site with a liquid composition, or by applying the compounds to the plant. solid form to the ground, for example, in granular form (application to the earth). With flooded rice crops, granules can be introduced into the flooded rice field. The compositions of the invention are also suitable for protecting the propagation material of plants, for example seeds, such as fruits, tubers, or grains, or seedlings, fungal infections and animal plagues. The propagation material can be treated with the composition before starting the culture, for example, by coating the seeds before planting. The active ingredients of the invention can also be applied to the seeds (coating), either by soaking the seeds in a liquid composition, or by coating them with a solid composition. The composition can also occur when the propagation material is introduced into the culture site, for example, when the seeds are sown in the seed furrow. The treatment methods for the plant propagation material, and the propagation material thus treated, are additional objects of the invention. The invention is illustrated by the following examples. These do not impose any limitation on the invention. Temperatures are given in degrees Celsius.

Preparation Examples Example Hl: Preparator, of 4-nitrobenzoic acid N '- (2,6-dichloro-4-trifluoromethylfer.-yl) -hydrazide of the formula: A solution of 2? . 3 - grams of 4-nitrobenzoyl chloride er. 150 milliliters of ichloromethane, is added dropwise over a period of about 60 minutes, to 45.1 grams of 2,6-dichloro-4-trifluoromethylphenylhydrazine in 1000 milliliters of dichloromethane with stirring at 0 ° C to 5 ° C, and then stirring is continued for an additional 60 minutes at room temperature. For 20 minutes, the mixture is stirred vigorously while feeding 20.4 grams of triethylamine. The stirring is then continued for 3 hours at room temperature. The organic phase is washed three times with 500 milliliters of water each time, dried over sodium sulfate, and the solvents are removed on the rotary evaporator. After recrystallization of the residue from toluene, the title product is obtained at a melting point of 188-190 ° C. Example H2: Preparation of 4-. { 1 - [(2,6-dichloro-4-trifluoromethylphenyl) hydrazono] -chloromethyl} -nitrobenzene of the formula: To a solution of. 69.3 grams of 4-nitrobenzoic acid N '- (2,6-dichloro-4-trifluoromethylphenyl) -hydrazide in 600 milliliters of toluene, 33.9 grams of thionyl chloride are added dropwise with stirring at room temperature. Then the mixture is heated to 105 ° C, and stirred for 6 hours. After cooling, the mixture is concentrated to dryness by evaporation in the rotary evaporator, and the residue is crystallized from toluene. The title compound is obtained with a melting point of 117-118 ° C (compound 1.20). Example H3: The other compounds listed in Table 1, can be prepared in a manner analogous to that described in Example H2. Table 1; Compounds of the formula: No. (R3a) n1 (Rsb) nZ p.f. ° C 1.1 2,6-CI2-4-CF3 4-Br 124-125 1.2 2,6-CI2-4-CF3 4-COCF3 107-108 1.3 2,6-CI2-4-CF3 3-NO2-4- Cl 141-143 1.4 2,6-CI2-4-CF3 2-F-4-NO2 88-90 1.5 2,6-CI2-4-CF3 4-SCF3 137-138 1.6 2.6-C! 2-4 -CF3 4-SCH3 89-90 1.7 2,4-CI2-6-CF3 4-NO2 128-129 1.8 2-CI-4-CF3-6-F 4-NO2 135-137 1.9 2,6-CI2-3 -F-4-CF3 4-NO2 143-144 1.10 2,3,6-CI3-4-CF3 4-NOz 121-123 1.11 2,4,6-CI3 4-SO2CH3 amorphous 1.12 2,4,6-Cls 4-SCH3 78-79 1.13 2,4,6-Cl 3 4-SCF 3 92-94 1.14 2,6-Cl 2 -4-CF 3 4-F 97-98 1.15 2,6-Cl 2 -4-CF 3 4-SO 2 N ( CH3) 2 163-164 1.16 2,4,6-CI3 4-CHO 152-154 1.17 2,6- (NO2) 2-4-CF3 4-NO2 189-191 1.18 2-C! -4-OCF3-6 -NO2 4-NO2 147-148 2-CI-4-CF3 3-NO2-4-CI 188-190 1.19 1.20 2,6-C! 2-4-CF3 4-N02 117-118 Example H4: Preparation of 4-. { 1 - [(2,6-dichloro-4-trifluoromethylphenyl) hydrazono] -2-nitriloethyl} Nitrobenzene of the formula: To 10.7 grams of sciense cyanide in 240 milliliters of water and 160 milliliters of ethanol, 51.5 grams of 4- are added. { l- [(2,6-dichloro-4-trifluoromethylphenyl) hydrazono] chloromethyl} -nitrobenzene solid in portions over a period of about 1 hour. The reaction mixture is stirred for 18 hours at room temperature, and then poured into 6 liters of ice water. The precipitate is filtered, washed three times with water, dissolved in ethyl acetate, and washed with a 15 percent NaCl solution. The organic phase is dried, filtered over sodium sulfate and concentrated to dryness by evaporation - in the rotary evaporator. The residue is crystallized from toluene. This provides the title compound with a melting point of 160-161 ° C.

Example H5: Preparation of 4-. { l- [(2,6-dichloro-4-trifluoromethylphenyl) -N-methyl-N-methoxycarbamoylhydrazono] -2-nitrilethyl} Nitrobenzene of the formula: A 1.2 grams of 4-. { 1- [(2,6-dichloro-4-trifluoromethylphenyl) -hydrazono] -2-nitriloethyl} nitrobenzene in 50 milliliters of tetrahydrofuran, 0.44 grams of finely powdered potassium terbutylate are added at room temperature. The mixture is stirred for 10 minutes, resulting in a deep red solution. 0.48 grams of methyl-methoxycarbamoyl chloride is added, and the mixture is stirred for 3 hours. The solvent is removed on the rotary evaporator, and the residue is dissolved in ethyl acetate. The ethyl acetate phase is washed with water and NaCl solution, dried over sodium sulfate, and concentrated to dryness by evaporation in vacuo. The residue is chromatographed on a column of silica gel with hexane: tetrahydrofuran in a ratio of 5: 1. Concentration by evaporation of fractions 6-14 yields the title compound with a melting point of 96-97 ° C (Compound 2.1).

Example 6: The other compounds listed in Tables 2 and 3 can also be prepared in a manner analogous to that described in Example H5.

Table 2; Compounds of the formula: C3H3F2cys is 2, 2-difluoro-cycloprop-1-yl 4-C (M0Me) CF3 means the substituent 4-C (= NOCH3) -CF3 No. (R3a) n1 (R3b) n2 R2 pf- (° C) 2. 1 2,6-CI2-4-CF3 4-NO2 -CON (OCH3) CH3 96-97 2. 2 2,6-CI2-4-CF3 4-NO2 -COSC2Hs 198-199 2. 3 2,6-CI2-4-CF3 - 4-NO2 -COSCHg 198-200 2. 4 2,6-CI2-4-CF3 4-NO2-CH2OC (O) C (CH3) 3 87-90 DO NOT. (Rs,), ni (Ra) n2 p.f. (° C) 2. 5 2.6 «CI2-4-CF3 4-NOz -CH2OC2H4OCH3 63-65 2. 6 2,6-CI2-4-CF3 4-NOz -CH2OCH2CH = CH2 73-74 2. 7 2,6-CI2-4-CF3 4-NO2 -CH2OCH2C = CH 99-100 2. 8 2,6-C! 2-4-CF3 4-SOCF3 -H 157-158 2. 9 2,6-Cl2-4-CF3 4-SO2CF3 -H 108-109 2. 10 2.6-C! 4-CF3 4-SCF3 -H 156 2. 11 2,6-Cl2-4-CF3 4-SOCF3-CH2OC2Hs oil 2. 12 2,6-CI2-4-CF3 4-SO2CF3 -CH2OC2p5 oil 2. 13 2,6-CI2-4-CF3 4-SCH3 -H 147-149 2. 14 2,6-CI2-4-CF3 4-SO2N (CH3) 2 -H 201-202 2. 15 2.6-C! 2-4-CF3 4-SO2N (CH3) 2 -CH2OC2H5 136 2. 16 2,6-C! 2-4-CF3 4-SCH3 -CH2OC2H5 80-81 2. 17 2,6-C! 2-4-CF3 4-F -H 126-128 2. 18 2,6-Cl2-4-CF3 4-F-CH2OC2Hs oil 2. 2. 85 2,6-CI2-4-CF3 4-SCF3 -COCH2C3H3F2cyc 75-77 2. 86 2.6-CI2-4-CF3 4-SOCF3 -COCH2C3H3F2cyc 114-115 2. 87 2,6-C! 2-4-CF3 4-SO2CF3 -COCH2C3H3F2cyc 154-155 2. 88 2-CI-4-CF3-6-F 4-NO2 -COCH2C3H3F2cyc 113-114 2. 89 2.6-CI2-3-F-4-CF3 4-NO2 -COCH2C3H3F2cyc 103-104 2. 90 2,4-CI2-6-CF3 4-NO2 -COCH2C3H3F2cyc 174-175 2. 91 2,4,6-Ci3 4-NO2 -COCH2C3H3F2cyc 153-154 2. 92 2,4,6-CI3 4-CN -COCH2C3H3F2cyc 134-135 2. 93 2,6-CI2-4-CF3 3-CH3-4-NO2 -COCH2C3H3F2cyc 138-139 2. 94 2,6-CI2-4-CF3 4-C (NOMe) CF3 -CH OC2Hs resin 2. 95 2,6-CI2-4-CF3 4-C (NOMe) CF3 -H 145-146 2. 96 2,4,6-CI3 4-C (NOMe) CF3 -CH2OC2Hs 92-93 2. 97 2,4,6-CI3 4-C (NOMe) CF3 -H 134-135 2. 2. 199 2,6-Cl2-4-NO2 4-SOC2F5 -CH2OC2Hs 2,200 2,6-CI2-4-NO2 4-SO2C2F5 -CH2OC2Hs 2,201 2,4-Cl2-6-CF3 4-SOC2F5 -CH2OC2Hs Resin 2. 202 2,4-CI2-6-CF3 4-SO C2Fs -CH2OC2Hs 108-110 2. 203 2,4,6-CI3 4-SOC2F5 -COOCH3 resin 2. 204 2,4,6-Cls 4-SO2C2Fs -COOCH3 131-133 2. 205 2-CI-4-CF3-6-F 4-SOC2F5 -COOCH3 resin 2. 206 2-CI-4-CF3-6-F 4-SO2C2Fs -COOCH3 resin 2. 207 2,3,6-CI3-4-CF3 4-SOC2F5 -COOCH3 resin 2. 208 2,3,6-CI3-4-CF3 4-SO2C2Fs -COOCH3 resin 2. 209 2,6-CI2-3-F-4-CF3 4-SOC2F5 -COOCH3 2,210 2,6-CI2-3-F-4-CF3 4-SO2C2F5 -COOCH3 2,211 2,6-C! 2-4-N02 4-SOC2Fs -COOCH3 2.212 2.6-CI2-4-NO2 4-SO2C2F5 -COOCH3 2.213 2.3.6-CI3-4-CF3 4-SOC2F5 -COOCH3 2.214 2.3.6-Ci3-4-CF3 4 -SO2C2Fs -COOCHg 2.215 2A6-CI3 4-SOC2F5 -COCH3 2,216 2,4,6-CI3 4-SO2C2Fs -COCH3 2,217 2,4,6-CI3 4-SCF2CHFCF3 -H 2,218 2,4,6-CI3 4-- H SOCF2CHFCF3 2,219 2,4,6-CI3 4- H SO2CF2CHFCF3 2,220 2,6-CI2-4-CF3 4-SCF2CHFCF3 -H2,221 2.6-CI2-4-CF3 4- H SOCF2CHFCF3 2.222 2.6- CI2-4-CF3 4- H SO2CF2CHFCF3 2,6- (NO2) 2-4-CF3 H -H 130-181 2,6- (NO 2) 2- H -H 4-CF3-5-CI 2,6- (NO 2) 2 H -H 2,6- (NO 2) 2-4-CF 3 4-NOz -CH 3 2,6 - (NO2) 2- 4-NOz -COOCH3 4-CF3-5-CI 2,6- (NO2) 2 4-NO2 -CH2OC2Hs 2,6- (NO2) 2-4-CF3 4-SCF3 -CH3 2, 6- (NO2) 2- 4-SOCF3 -COOCH3 4-CF3-5-CI 2,6- (NO2) 2 4-SON (CH3) 2 -CH2OC2Hs 2,6- (NO2) 2-4-CF3 4- SO2N (CH3) 2 -CH2OCH (CH3) 2,6- (NO2) 2-4-SCH3 -COCH2C3H3F2cyc 4-CF3-5-CI 2,6- (NO2) 2 4-F -COCH2OC6H4-4-F 2 , 6- (NO2) 2-4-CF3 4-Br -CH3 2,6- (NO2) 2- 4-SOCF3 -COOCH3 4-CF3-5-F 2,6- (NO2) 2 4-F -CH OC2Hs 2,6- (NO2) 2-4-CF3 4-Br -CH3 2,6- (NO2) 2-4- 4-SOCF3 -COOCH3 CF3-5-F 2,6- (NO2) 2 4-F -CH2OC2Hs 2,6- (NO2) 2-4-CF3 4-Br -CH2OCH (CH3) 2 2,6- (NO2) 2-4-SOCF3 -COCH2C3H3F2cyc 4-CF3-5-CI 2,6- (NO2) ) 2 4-SOCF3 -COCH2OC6H4-4-F Table 3: Compound of the formula: . (R3a) ", A2 H2 p.f. (»C) 2,6-CI2-4-CF3 X) -H * 2,6-CI2-4-CF3 X) -CH2OC2H5 2,6-Cl2-4-CF3 X) -H 8 2,6-CI2-4-CF3 x? - -H 169-170 9 2.6-CI2-4-CF3 x- -H 128-132 2,6-CI2-4-CF3 -H ^ 11 2,6-C! 2-4-CF3 -H 152-153 .12 2,6-CI2-4-CF3 -COCH3 192 3a) "? R2 p.f (-O) , 6- (NO2) 2 x > - -H , 6- (NO2) 2-4-CF3 x > ^ - -CH3 , 6- (NO2) 2-4-CF3-5-CI x > '- ° - -COCH3 , 6- (NO2) 2 x > - ° - -COCH2C3H3F2cyc , 6- (NO2) 2-4-CF3 s N H ^ \ lt, 6- (NO2) 2-4-CF3-5-CI N -CH3? _ / > 2,6- (NO 2) 2-4-CF 3 s N -COCH 2 C 3 H 3 F 2cyc Table A A.1) -CON (OCH 3) CH 3 4-CN A.2) -CON (OCH 3) CH 3 4-NO 2 A.3) -CON (OCH3) CH3 4-CF3 A.4) -CON (OCH3) CH3 2-Cl-4-NO2 A.5) -CON (OCH3) CH3 3-CH3-4-NO2 A.6) -CON (OCH3) CH3 4-Cl A.7) -CON (OCH3) CH3 4-C6H4-4-NO2 A.8) -CON (OCH3) CH3 4-C6H4-2-NO2 A.9) -CON (OCH3) CH3 4-SCF3 A.10) -CON (OCH3) CH3 4-SOCF3 A.11) -CON (OCH3) CH3 4-SO2CF3 A.12) -CON (OCH3) CH3 2-F-4-CN A.13) -CON (OCH3) CH3 2-F- 4-NO2 A.14) -CON (OCH3) CH3 4-COCF3 A.15) -CON (OCH3) CH3 4-CHO A.16) -CON (OCH3) CH3 4-CI-3-NO2 A.17) -CON (OCH3) CH3 4-NH2 A.18) -CON (OCH3) CH3 3-CI-4-CN A.19) -CON (OCH3) CH3 3-OCH3-4-NO2 A.20) -CON (OCH3) CH3 3-CI-4-NO2 A.21) -CON (OCH3) CH3 3-F-4-NO2 A.22) -CON (OCH3) CH3 4-C6H4-4-CN A.23) -CON (OCH3) CH3 4-C6H4-2-CN A.24) -C (O) NHOCH3 4-CN A.25) -C (O) NHOCH3 4-NO2 A.26) -C (O) NHOCH3 4-CF3 A.27) -C (O) NHOCH3 2-Cl-4-NOz A.28) -C (O) NHOCH3 3-CH3-4-NO2 A.29) -C (O) NHOCH3 4-Cl A.30) -C (O) NHOCH3 4-C6H4-4-NO2 • 0 \ A.63) -COSC2H5 4-NH2 A.64) -COSC2H5 3-C1-4-CN A.65) -COSC2H5 3-OCH3-4-NO2 A.66) -COSC2H5 3-CI-4-NO2 A.67) -COSC2H5 3-F-4-NO2 A.68) -COSC2H5 4-C6H4-4-CN A.69) -COSC2H5 4-C6H4-2-CN GARLIC) -COSCH3 4-CN A.71) -COSCH3 4-NO2 A.72) -COSCH3 4-CF3 A.73) -COSCH3 2-Cl-4-NO2 A.74) -COSCH3 3-CH3-4-NO2 A.75) -COSCH3 4-CI A.76) -COSCH3 4-C6H4-4-NO2 A.77) -COSCH3 4-C6H4-2-NO2 A.78) -COSCH3 4-SCF3 A.79) -COSCH3 4-SOCF3 A.80) -COSCH3 4-SO2CF3 A.81) -COSCH3 2-F-4-CN A.82) -COSCH3 2-F- 4-NO2 A.83) -COSCH3 4-COCF3 A.84) -COSCH3 4-CHO A.85) -COSCH3 4-Cl- 3-NO2 A.86) -COSCH3 4-NH2 A.87) -COSCH3 3-CI-4-CN A.88) -COSCH3 3-OCH3-4-NO2 A.89) -COSCH3 3-CI-4-NO2 A.90) -COSCH3 3-F-4-NO2 A.91) -COSCH3 4-C6H4-4-CN A.92) -COSCH3 4-C6H4-2-CN A.93) -CH2OC (O) C (CH3) 3 4-CN A.94) -CH2? C (O) C (CH3) 3 4-NO2 A.95) -CH2OC (O) C (CH3) 3 4-CF3 A.96) -CH2OC (O) C (CH3) 3 2-Cl-4-NO2 A.97) -CH2OC (O) C (CH3) 3 3-CH3-4-NO2 A.98) -CH2OC (O) C (CH3) 3 4-Cl A.99) -CH2OC (O) C (CH3) 3 4-C6H4-4-NO2 A.100) -CH2OC (O) C (CH3) 3 4-C6H4-2-NO2 A.101) -CH2OC (O) C (CH3) 3 4-SCF3 A.102) -CH2OC (O) C (CH3) 3 4-SOCF3 A.103) -CH2OC (O) C (CH3) 3 4-SO2CF3 A.104) -CH2OC (O) C (CH3) 3 2-F-4-CN A.105) -CH2OC (O) C (CH3) 3 2-F- 4-NO2 A.106) -CH2OC (O) C (CH3) 3 4-COCF-, A.107) -CH2OC (O) C (CH3) 3 4-CHO A.108) -CH2OC (O) C (CH3) 3 4-CI-3-NO2 A.109) -CH * 2OC (O) C (CH3) 3 4-NH2 A.110) -CH2OC (O) C (CH3) 3 3-CI-4-CN A.111) -CH2OC (O) C (CH3) 3 3-ORCH3-4-N02 A.112) -CH2OC (O) C (CH3) 3 3-Cl-4-NO2 A.113) -CH2OC (O) C (CH3) 3 3-F-4-NO2 A.114) -CH2OC (O) C (CH3) 3 4-C6H4-4-CN A.115) -CH2OC (O) C (CH3) 3 4-C6H4-2-CN A.116) -CH2OC2H4OCH3 4-CN A.117) -CH2OC2H4OCH3 4-NO2 A.118) -CH2OC2H4OCH3 4-CF3 A.119) -CH2OC2H4OCH3 2-Cl-4-NOz A.120) -CH2OC2H4OCH3 3-CH3-4-NO2 A.121) -CH2OC2H4OCH3 4-Cl A.122) -CH2OC2H4OCH3 4-C6H4-4-NO2 A.123) -CH2OC2H4OCH3 4-C6H4-2-NO2 A.124) -CH2OC2H4OCH3 4-SCF3 A.125) -CH2OC2H4OCH3 4-SOCF3 A.126) -CH2OC2H4OCH3 4-SO2CF3 > > > > > > > > > > > > > > > > > > > > > > > > > > > > > > > > cn cn cn n Cn Oí n cn cn 4a. 4a. 4a. 4 4a »- 4a. 4a. 4a »4a» co co o co CO? ? ? co ro ro ro 00 n a. ? ro or CD 00 cn n 4a. or ro O CO? CD n 4a »? ro O CD 00 VO • A.221) -H SCF2Br A.222) -H SOCF2Br A.223) -H SO2CF2Br A.224) -H SCF2CF2Br A.225) -H SOCF2CF2Br A.226) -H SO2CF2CF2Br A.227) -CH3 4-SCF3 A.228) -CH3 4-SOCF3 A.229) -CH3 4-SO2CF3 A.230) -CH3 4-SC2F5 A.231) -CH3 4-SOC2F5 A.232) -CH3 4-SO2C2F5 A.233) -CH3 4-SCF2H A.234) -CH3 4-SOCF2H A.235) -CH3 4-SO2CF2H A.236) -CH3 4-SCF2CI A.237) -CH3 4-SOCF2CI A.238) -CH3 4-S02CF2CI A.239) -CH3 4-SF5 A.240) -CH3 SCF2Br A.241) -CH3 SOCF2Br A.242) -CH3 SO2CF2Br A.243) -CH3 SCF2CF2Br A.244) -CH3 SOCF2CF2Br A.245) -CH3 S02CF2CF2Br A.246) -C2H5 4-SCF3 A.247) -C2Hs 4-SOCF3 A.248) -C2Hs 4-SO2CF3 A.249) -C2Hs 4-SC2F5 A.250) -C2Hs 4-SOC2F5 A.251) -C2Hs 4-SO2C2F5 A.252) -C2Hs 4-SCF2H R5 (R »), m A.253) -C2H5 4-SOCF2H A.254) -C2H5 4-SO2CF2H A.255) -C2H5 4-SCF2CI A.256) -C2H5 4-SOCF2CI A.257) -C2H5 4-SO2CF2CI A.258) -C2H5 4-SF5 A.259) -C2Hs SCF2Br A.260) -C2Hs SOCF2Br A.261) -C2H5 SO2CF2Br A.262) -C2H5 SCF2CF2Br A.263) -C2H5 SOCF2CF2Br A.264) -C2H5 SO2CF2CF2Br A.265) -CH (CH3) 2 4-SCF3 A.266) -CH (CH3) 2 4-SOCF3 A.267) -CH (CH3) 2 4-SO2CF3 A.268) -CH (CH3) 2 4-SC2F5 A.269) -CH (CH3) 2 4-SOC2F5 A.270) -CH (CH3) 2 4-SO2C2F5 A.271) -CH (CH3) 2 4-SCF2H A.272) -CH (CH3) 2 4-SOCF2H A.273) -CH (CH3) 2 4-SO2CF2H A.274) -CH (CH3) 2 4-SCF2CI A.275) -CH (CH3) 2 4-SOCF2CI A.276) -CH (CH3) 2 4-SO2CF2Ci A.277) -CH (CH3) 2 4-SF5 A.278) -CH (CH3) 2 SCF2Br A.279) -CH (CH3) 2 SOCF2Br A.280) -CH (CH3) 2 SO2CF2Br A.281) -CH (CH3) 2 SCF2CF2Br A.282) -CH (CH3) 2 SOCF2CF2Br A.283) -CH (CH3) 2 SO2CF2CF2Br A.284) -COCH3 4-SCF3 A.287) -COCH3 4-SC2F5 A.289) -COCH3 4-SO2C2F5 A.291) -COCH3 • 4-SOCF2H A.294) -COCH3 4-SOCF2CI A.295) -COCH3 4-SO2CF2CI A.297) -COCH3 SCFzBr SOCFzBr A.301) -COCH3 SOCF2CF2Br A.303) -COC2H5 4-SCF3 A.305) -COC2H5 4-SO2CF3 A.306) -COC2H5 4-SC2F5 A.307) -COC2H5 4-SOC2F5 A.308) -COC2H5 4-SO2C2Fs A.309) -COC2H5 4-SCF2H 4-SOCF2H A.310) -COC2Hs 5 4-SO2CF2H A.311) -COC2H A.312) -COC2H5 4-SCF2CI A.313) -COC2H5 > 4-SOCF2CI A.314) -COC2H5 4-SO2CF2CI (R *), n2 A.381) -CH2OCH3 4-SO2CF3 A.382) -CH2OCH3 4-SC2F5 A.383) -CH2OCH3 4-SOC2F5 A.384) -CH2OCH3 4-SO2C2F5 A.385) -CH2OCH3 4-SCF2H A.386) -CH2OCH3 4-SOCFzH A.387) -CH2OCH3 4-SO2CF2H A.388) -CH2OCH3 4-SCF2CI A.389) -CH2OCH3 4-SOCFzCI A.390) -CH2OCH3 4-SO2CF2CI A.391) -CH2OCH3 4-SF5 A.392) -CH2OCH3 SCF2Br A.393) -CH2OCH3 SOCF2Br A.394) -CH2OCH3 SO2CF2Br A.395) -CH2OCH3 SCF2CF2Br A.396) -CH2OCH3 SOCF2CF2Br A.397) -CH2OCH3 SO2CF2CF2Br A.398) -CH2O-n-C3H7 4-SCF3 A.399) -CH2O-n-C3H7 4-SOCF3 A.400) -CH2O-n-C3H7 4-SO2CF3 A.401) -CH2O-n-C3H7 4-SCzF5 A.402) -CH2O-n-C3H7 4-SOCzFs A.403) -CH2O-n-C3H7 4-SO2C2F5 A.404) -CH2O-n-C3H7 4-SCF2H A.405) -CH2O-n-C3H7 4-SOCF2H A.406) -CH2O-n-C3H7 4-SO2CF2H A.407) -CH2O-n-C3H7 4-SCF2CI A.408) -CH2O-n-C3H7 4rSOCF2CI A.409) -CH2O-n-C3H7 4-SO2CF2CI A.410) -CH2O-n-C3H7 4-SF5 A.411) -CH2O-n-C3H7 SCF2Br A.412) -CH2O-n-C3H7 SOCF2Br oo r- R2 (R »), n2 A.445) -CH2N (CH3) S? 2CH3 4-SCF2CI A.446) -CH2N (CH3) SO2CH3 4-SOCF2CI A.447) -CH2N (CH3) S? 2CH3 4-SO2CF2CI A.448) -CH2N (CH3) SO2CH3 4-SF5 A.449) -CH2N (CH3) S? 2CH3 SCF2Br A.450) -CH2N (CH3) S? 2CH3 SOCF2Br A.451) -CH2N (CH3) SO2CH3 SO2CF2Br A.452) -CH2N (CH3) SO2CH3 SCFzCFzBr A.453) -CH2N (CH3) S02CH3 SOCF2CF2Br A.454) -CH2N (CH3) S02CH3 SO2CF2CF2Br Table 4: Compounds of the general formula wherein (R3a) nl is 2, 6-Cl2-4-CF3, and R2 and (R-jb) ^ each correspond to a line of Table A. Table 5; Compounds of the general formula (Ib), wherein (R3a) nl is 2 / 4,6-Cl3, and R2 and (R3b) ^ each correspond to a line of Table A. Table 6; Compounds of the general formula (Ib), wherein (R3a) nl is 2-Cl-4-CF3, and R2 and (R3b) n each correspond to a line of Table A.

Table 7: Compounds of the general formula (Ib), wherein (R3a) nl is 2, 6-Cl2-4-N02, and R2 and (3b) p2 each correspond to a line of Table A. Table 8; Compounds of the general formula (Ib), wherein (R3a) nl is 2,6-Cl2-4-OCF3, and R2 and (R3b) n2. each correspond to a line of Table A. Table 9t Compounds of the general formula (Ib), wherein (R3a) nl is 2,6-Cl2-4-F, and R2 and (3b) n2 each correspond to one line of Table A. Table 10; Compounds of the general formula (Ib), wherein (R3a) nl is 2, 6-Cl2-4-Br, and R2 and (R3b) n2 each correspond to a line of Table A. Table 11t Compounds of the formula general (Ib), wherein (R3a) nl is 2-Cl-4-CF3-6-F, and R2 and (R3) "2 each correspond to a line of Table A. Table 12: Compounds of the formula general (Ib), wherein (R3a) nl is 2,3,6-Cl3-4-CF3, and R2 and (R3b) n each correspond to a line of Table A.

Table 13: Compounds of the general formula (Ib), wherein (R3a) nl is 2/6-Cl2-3-F-4-CF3, and R2 and (R3b) n each correspond to a line of Table A Table 14; Compounds of the general formula (Ib), wherein (R3a) nl is 2,3-F2-4-CF3-6-Cl, and R2 and (R3b) n each correspond to a line of Table A. Table 15 Compounds of the general formula (Ib), wherein (R3a) nl is 2,6-Cl-4-CN, and R2 and (R3b) n each correspond to a line of Table A. Table 16; Compounds of the general formula (Ib), wherein (R3a) nl is 2,4-Cl2-6-CF3, and R2 and (3b) n2 each correspond to a line of Table A. Table 17: Compounds of the general formula (Ib), wherein (R3a) nl is 2.6-CI2-4-SCF3, and R2 and (3b) n2 each correspond to a line of Table A. Table 18: Compounds of the general formula (Ib) , wherein (R3a) nl is 2, 6-Cl2-4-SOCF3, and R2 and (3b) n2 each correspond to a line of Table A.

Table 19: Compounds of the general formula (Ib), wherein (R3a) nl is 2.6-Cl2-4-S02CF3 and R2 and (3b) n2 each correspond to a line of Table A. Table 20: Compounds of the general formula (Ib), wherein (R3a) nl is 2, 6-Cl2-4-S02CH3 and Rj and (3b) n2 each correspond to a line of Table A. Table 21: Compounds of the general formula (Ib), where (R3a) "? is 2, 6-Cl2-4-OCF2Br and R2 and (Rsb) ^ each correspond to a line of Table A. Table 22: Compounds of the general formula (Ib), wherein (R3a) nl is 2, 6 -Cl2-4-OCF2H and R2 and (R3b) ^ each correspond to a line of Table A. Table 23: Compounds of the general formula (Ib), where (R3a) "? is 2, 6-Cl2-4-C2F5 and R2 and (R3b) n2 each correspond to a line of Table A. Table 24: Compounds of the general formula (Ib), wherein (R3a) nl is 2, 6 - (N02) 2-4-CF3 and R2 and (3b) n2 each correspond to a line of Table A.

Table 25; Compounds of the general formula (Ib), wherein (R3a) nl is 2.6- (N02) 2-4-Cl and R2 and (R3b) n2 each correspond to a line of Table A. Table 26: Compounds of the general formula (Ib), wherein (R3a) nl is 2,6-Cl2- -OS02CH3 and R2 and (ab), ^ each corresponds to a line of Table A. Table 27: Compounds of the general formula (Ib), wherein ( R3a) n? is 2,6-Cl2-4-OS02CF3 and R2 and (R3b) ^ each correspond to a line of Table A. Table 28: Compounds of the general formula (Ib), wherein (R3a) m is 2, 6 -Cl2-4-SF5 and R2 and (R3b) ^ each correspond to a line of Table A. Examples of the formulations of the compounds of the invention, ie solutions, granulates, dry powders, wettable powders, emulsifiable concentrates , coated granules, and suspension concentrates, are of the types listed, for example, in European Patent Number EP-A-580,553 (Case 19164), Examples Fl to FIO.

Biological Examples Example Bl: Ovicidal effect on Heliothis virescens The eggs of Heliothis virescens deposited on filter paper are briefly immersed in a test solution comprising 400 ppm of the mixture of active ingredients to be tested in acetone / water. After the test solution is dried, the eggs are incubated in Petri dishes. After 6 days, the percentage of hatching of the eggs is compared with that for the untreated controls (percentage of reduction in the hatching index). The compounds listed in Tables 3 to 5 show good activity against Heliothis virescens. In particular, compounds 2.1 to 2.5, 2.8 to 2.13, and 3.7, show a response greater than 80 percent.

Example B2; Effect on caterpillars of Spodoptera li ttoralis Young soybean plants are sprayed with an aqueous emulsion containing 400 ppm of active ingredient. After the sprayed tank is dried, the soybean plants are populated with 10 larvae in the third ing of Spodoptera li ttoralis, and placed in a plastic container. Three days later, they are evaluated. The percentage of reduction of the population, and the percentage of reduction in the damage by feeding (percentage of response), is determined by comparing the number of dead larvae and the degree of damage by feeding in the treated plants, with those in the plants not treated. The compounds of Table 1 show good efficacy against Spodoptera littoralis in this test. In particular, compounds 2.1 to 2.5, 2.7 to 2.18, and 3.7 to 3.9 show a response greater than 80 percent.

Example B3; Effect on larvae of Diabrotica balteata. The corn seedlings are sprayed with an aqueous emulsion containing 400 ppm of active ingredient. After the sprayed tank is dried, the corn seedlings are inoculated with 10 larvae in the second Diabrotica bal teata seedling, and placed in a plastic container. Six days later they are evaluated. The percentage of reduction of the population (percentage of response) is determined by comparing the number of dead larvae in the treated plants, with that in the untreated plants. The compounds of Tables 3 to 5 show good efficacy against Diabrotica balteata in this test. In particular, compounds 2.1 to 2.4, 2.6, 2.7, 2.11, 2.25 to 2.28, and 3.9, show a response greater than 80 percent.

Example B4: Effect on caterpillars of Plutella xylostella. The young cabbage plants are sprayed with an aqueous emulsion containing 400 ppm of active ingredient. After the sprayed tank is dried, the cabbage plants are populated with 10 larvae in the third seedling of Plutella xylostella, and placed in a plastic container. Three days later, they are evaluated. The percentage of reduction of the population, and the percentage of reduction in feeding damage (percentage of response), are determined by comparing the number of dead larvae and the degree of feeding damage in the treated plants, with those in the untreated plants. The compounds of Tables 3 to 5 show good efficacy against Plutella xylostella in this test.

Example B5: Effect on Tetranychus urticae Young bean plants are inoculated with a mixed population of Tetranychus urticae, and one day later, they are sprayed with an aqueous emulsion containing 400 ppm of active ingredient. The plants are incubated for 6 days at 25 ° C, and then evaluated. The percentage of reduction of the population (percentage of response) is determined by comparing the number of eggs, larvae, and dead adults in the treated plants, with that in the untreated plants. The compounds of Tables 3 to 5 show good efficacy against Tetranychus urticae in this test.

Example B6: Effect on Aphis craccivora Pea seedlings are infected with Aphis craccivora, then sprayed with an emulsion containing 400 ppm of active ingredient, and incubated at 20 ° C. Three and six days after they are evaluated. The percentage of reduction of the population (percentage of response) is determined by comparing the number of dead aphids in the treated plants, with that in the untreated plants. The compounds of Tables 3 to 5 show good efficacy against Aphis craccivora in this test. In particular, compounds 2.7, 2.22, and 3.8 show a good response greater than 80 percent.

Example B7: Effect on Myzus persicae Pea seedlings are infected with Myzus persicae, then sprayed with an emulsion containing 400 ppm of active ingredient, and incubated at 20 ° C. Three and six days later, they are evaluated. The percentage of population reduction (percentage of response) is determined by comparing the number of dead aphids in the treated plants, with that in the untreated plants. The compounds of Tables 3 to 5 show good efficacy against? Fyzus persicae in this test. In particular, compounds 3.7 and 3.13 show a good response greater than 80 percent.

Claims (14)

1. CLAIMS A compound of the formula: wherein: AL and Aa are independent of each other, and in each case represent a monocyclic or bicyclic aryl or heteroaryl radical, and each heteroaryl radical independently of the other has from 1 to and including 4 heteroatoms selected from the group consisting of in N, O, and S; and x is substituted where appropriate with a substituent (R3) m 'and A2' where appropriate, with a substituent (R3b) n2; nx and n2 are independently of each other, 1, 2, 3, or 4, depending on the possibilities of substitution in the ring system At and K¿; and any of: (A) R3a and R3b, independently of one another, are hydrogen, halogen, alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkenyl of 2 to 4 carbon atoms, alkynyl of 2 to 4 carbon atoms, haloalkenyl of 2 to 4 carbon atoms, haloalkynyl of 2 to 4 carbon atoms, alkoxy of 1 to 6 carbon atoms, haloalkoxy of 1 to 6 carbon atoms, alkenyloxy of 2 to 6 carbon atoms, alkynyloxy of 2 to 6 carbon atoms, haloalkeno-nyloxy of 2 to 6 carbon atoms, haloalkynyloxy of 2 to 6 carbon atoms, -OH, -SF5, -CHO, - C (= 0) - alkyl of 1 to 6 carbon atoms, -C (= 0) -haloalkyl of 1 to 6 carbon atoms, -C (= 0) -O-alkyl of 1 to 6 carbon atoms, -C (= 0) - O-haloalkyl of 1 to 6 carbon atoms, -0-C (= 0) N (R6) 2 (wherein both substituents R6 are independent of each other), -CN, -N02, -S (= 0) 2N (R6) 2 (wherein both substituents R6 are independent of each other), -S (= 0) p-alkyl d and 1 to 6 carbon atoms, -S (= 0) p-haloalkyl of 1 to 6 carbon atoms, -O- S (= 0) - alkyl of 1 to carbon atoms, -0-S (= 0) ), haloalkyl of 1 to 6 carbon atoms, phenyl, benzyl, phenoxy, or benzyloxy, wherein each of the phenyl, benzyl, phenoxy, or benzyloxy radicals is unsubstituted or substituted on the aromatic ring independently of each other, 1 to 5 times, with substituents selected from the group consisting of halogen, cyano, N02, alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, and haloalkoxy from 1 to 6 carbon atoms; and Rs is R ^. or (B) R3a and R3b, independently of one another, are as defined in (A), and at least one of the radicals R '3- a R 3.b is -CRS = CR5R14, - R ^ R ^, - C (= 0) CN, -C (= 0) C (= 0) O-alkyl of 1 to 6 carbon atoms, -CR15 = NOR10 or a 5 or 6 membered heteroaryl ring, wherein the ring of heteroaryl is substituted, where appropriate, depending on the possibilities of substitution in the ring, with 1 to 3 substituents selected from the group consisting of halogen, alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 4 carbon atoms , NOz, and CN; and R2 is R2a or R2b; or (C) R3a has one of the meanings defined hereinbefore in (A) or (B); R3b is hydrogen, halogen, alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkenyl of 2 to 4 carbon atoms, alkynyl of 2 to 4 carbon atoms, haloalkenyl of 2 to 4 carbon atoms , haloalkynyl of 2 to 4 carbon atoms, alkoxy of 1 to 6 carbon atoms, haloalkoxy of 1 to 6 carbon atoms, alkenyloxy of 2 to 6 carbon atoms, alkynyloxy of 2 to 6 carbon atoms, haloalkenyloxy of 2 to 6 carbon atoms, haloalkynyloxyl of 2 to 6 carbon atoms, -OH, -SF 5 -CHO, -C (= 0) -alkyl of 1 to 6 carbon atoms, -C (= 0) -haloalkyl of 1 to 6 carbon atoms, -C (= 0) -O-alkyl of 1 to 6 carbon atoms, -C (= 0) -O-haloalkyl of 1 to 6 carbon atoms, -OC (= 0) N (R6 ) 2 (wherein the two substituents Re are independent of each other), -CN, -N02, phenyl, benzyl, phenoxy, or benzyloxy, wherein each of the phenyl, benzyl, phenoxy, or benzyloxy radicals is unsubstituted or substituted in the Aromatic ring, independently of one another, from 1 to 5 times, with substituents selected from the group consisting of halogen, cyano, N02, alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkoxy 1 5 to 6 carbon atoms, and haloalkoxy of 1 to 6 carbon atoms; -S (O) p-alkyl of 1 to 6 carbon atoms in the 4-position, or -S (= 0) p-haloalkyl of 1 to 6 carbon atoms in the 4-position, with the proviso that one of the substituents R3b is -S (= 0) p-alkyl of 1 to 6 carbon atoms or S (= 0) p-10 haloalkyl of 1 to 6 carbon atoms; and R2 S R2a ^ -2bi and in groups (A), (B) and (C), where appropriate, R2a is alkyl of 1 to 6 carbon atoms-NR ^ R ^, -C (= X ) - R7a, -CO-alkyl of 9 to 20 carbon atoms, -CH20 (C = 0) - alkyl of 1 to 6 carbon atoms, -alkyl of 1 to 6 carbon atoms -O-alkyl of 1 to 6 carbon atoms-O-alkyl of 1 to 6 carbon atoms, -CH20 (C = 0) alkenyl of 2 to 6 atoms of t tf carbon, -CH20 (C = 0) alkynyl of 2 to 6 carbon atoms, - C (= S) O-alkenyl of 2 to 6 carbon atoms, -C (= S) O-alkynyl 20 of 2 to 6 carbon atoms, -C (= S) S-alkyl of 1 to 6 carbon atoms, -C (= S) S-alkenyl of 2 to 6 carbon atoms, - C (= S) S -alkynyl of 2 to 6 carbon atoms, -C (= 0) S-alkyl of 1 to 6 carbon atoms, -C. { = 0) S-alkenyl of 2 to 6 carbon atoms, -C (= 0) S-alkynyl of 2 to 6 carbon atoms, -25 C (= S) NR11R12, -C (= 0) NR10OR13, -C 20-alkenyl of 2 to 6 carbon atoms, -CH20-alkynyl of 2 to 6 carbon atoms, -CH20-haloalkenyl of 2 to 6 carbon atoms, or -CH20-haloalkynyl of 2 to 6 carbon atoms; R2b is hydrogen, -OH, alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, alkenyl of 3 to 6 carbon atoms, alkynyl of 3 to 6 carbon atoms carbon, haloalkyl of 1 to 6 carbon atoms, haloalkenyl of 3 to 6 carbon atoms, haloalkynyl of 3 to 6 carbon atoms, benzyl, or benzoyl, wherein the benzyl or benzoyl radical is substituted on the aromatic ring, independently one of the other, from 1 to 3 times, by substituents selected from the group consisting of halogen, -CN, NOz, alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, and haloalkoxy of 1 to 6 carbon atoms; C 1 -C 6 alkoxy-C 1-6 -alkyl, cyanoalkyl of 1 to 6 carbon atoms, -C (= X) -R7a, -C (= X) -R7b, -0C (= 0 ) -R7a, -C (= 0) -C (= 0) -R7a, -0C (= 0) -R7b, -C (= 0) -C (= 0) -R7b, S (= 0) pN ( R6) 2 (wherein the two substituents R6 are independent of one another); cyano, -alkyl of 1 to 6 carbon atoms-N (R5) -C (= 0) -Rβ, -alkyl of 1 to 6 carbon atoms-SC (= S) -R8, -alkyl of 1 to 6 atoms carbon-S (= 0) p-R9, -S (= 0) p-R9, or -CH2-N (R10) -SO2-R9; X is O or S; p is 0, 1, or 2; Rs is independently H or alkyl of 1 to 8 carbon atoms; R6 is independently H, alkyl of 1 to 8 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, phenyl, or benzyl, wherein the phenyl or benzyl group is substituted on the aromatic ring, where appropriate, independently one of the another, 1 to 3 times, with substituents selected from the group consisting of halogen, -CN, N02, alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 4 carbon atoms, haloalkyl of 1 to 6 carbon atoms carbon, and haloalkoxy of 1 to 6 carbon atoms; or two alkyl radicals R6, together with the nitrogen atom with which they are bound, form a ring of 5 to 7 members, wherein a CH2 group, where appropriate, is substituted by a heteroatom selected from the group consisting of in O and S, or is substituted by NH, and wherein the 5- to 7-membered ring, where appropriate, is substituted once or twice with alkyl of 1 to 4 carbon atoms; R7a is alkoxy of 1 to 6 carbon atoms-alkyl of 1 to 6 carbon atoms, CH2CH2CF2C1, thioalkyl of 1 to 6 carbon atoms-alkyl of 1 to 6 carbon atoms, acyloxyalkyl of 1 to 6 carbon atoms, halocycloalkyl from 3 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms-alkyl of 1 to 6 carbon atoms, halocycloalkyl of 3 to 6 carbon atoms-alkyl of 1 to 6 carbon atoms, aryloxyalkyl of 1 to 6 atoms of carbon; or phenyl, benzyl, phenoxy, or aryloxyalkyl of 1 to 6 carbon atoms, which are substituted with 1 to 3 substituents selected from the group consisting of halogen, nitro, cyano, alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 4 carbon atoms, and haloalkoxy of 1 to 4 carbon atoms; RTÍ, is H, alkyl of 1 to 8 carbon atoms, alkenyl of 2 to 8 carbon atoms, haloalkyl of 1 to 8 carbon atoms, haloalkenyl of 2 to 8 carbon atoms, alkoxy of 1 to 8 carbon atoms, haloalkoxy of 1 to 8 carbon atoms, cycloalkyl of 3 to 6 carbon atoms carbon, phenyl, benzyl, phenoxy, benzyloxy, or -N (R6) 2 (wherein both R6 are independent of each other); R8 is alkyl of 1 to 8 carbon atoms, alkoxy of 1 to 8 carbon atoms, haloalkyl of 1 to 8 carbon atoms, haloalkoxy of 1 to 8 carbon atoms, thioalkyl of 1 to 8 carbon atoms, phenyl, benzyl , or -N (R6) 2 (where the two R6 radicals are independent of each other); R9 is alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 4 carbon atoms, or aryl, which is unsubstituted or substituted 1 to 3 times, independently of one another, with substituents selected from the group consisting of alkyl from 1 to 6 carbon atoms, alkenyl of 2 to 4 carbon atoms, alkynyl of 2 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, halogen, cyano, haloalkyl of 1 to 4 carbon atoms, haloalkenyl of 2 to 4 carbon atoms, haloalkynyl of 2 to 4 carbon atoms, haloalkoxy of 1 to 4 carbon atoms, and nitro; R10 is H, alkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, phenyl, or benzyl, wherein the phenyl and benzyl radicals are unsubstituted or substituted in the aromatic ring 1 to 3 times, independently one of the other, with substituents selected from the group consisting of alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, halogen, cyano, haloalkyl of 1 to 4 carbon atoms, haloalkoxy of 1 to 4 carbon atoms, and nitro; Ru and Ri2 are, independently of one another, H, alkyl of 1 to 6 carbon atoms, phenyl, -CO-alkyl of 1 to 6 carbon atoms, -CO-haloalkyl of 1 to 6 carbon atoms, - CO-phenyl, or together they form a saturated or unsaturated ring of 5 or 6 members, where, if appropriate, one or more, especially one, of the CH- or CH2- groups is or is substituted by a heteroatom selected from of the group consisting of O, N, and S, and wherein the 5 or 6 membered ring, if appropriate, independently of one another, is substituted with 1 to 3 substituents selected from the group consisting of halogen, alkyl from 1 to 4 carbon atoms, haloalkyl of 1 to 4 carbon atoms, haloalkoxy of 1 to 4 carbon atoms, N02, and CN; or the two substituents Rxl and R12 together form a ring: q is 2 or 3; and R 13 is H, alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms; R 14 is hydrogen, alkyl of 1 to 6 carbon atoms, haloalkyl of 3 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, haloalkoxy of 1 to 6 carbon atoms, alkenyloxy of 2 to 6 carbon atoms, - CHO, -C (= 0) -alkyl of 1 to 6 carbon atoms, -C (= 0) -haloalkyl of 1 to 6 carbon atoms, -C (= 0) -O-alkyl of 1 to 6 carbon atoms carbon, -C (= 0) -O-haloalkyl of 1 to 6 carbon atoms, -CN, -N02, - (wherein the two substituents R6 are independent of each other), -S (= 0) p-alkyl from 1 to 6 carbon atoms, -S (= 0) p-haloalkyl of 1 to 6 carbon atoms, -0-S (= 0) p-alkyl of 1 to 6 carbon atoms, -0-S (= 0) phaloalkyl of 1 to 6 carbon atoms, phenyl, benzyl, or benzyloxy, wherein each of the substituents of phenyl, benzyl or benzyloxyl is unsubstituted or substituted on the aromatic ring, independently of each other, 1 to 5 times, with substituents selected from the group consisting of halogen, cyano, N02, al 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, and haloalkoxy of 1 to 6 carbon atoms; and R1S is hydrogen, alkyl of 1 to 6 carbon atoms, or haloalkyl of 1 to 6 carbon atoms; and if appropriate, to the possible E / Z isomers, mixture of E / Z isomers, and / or tautomers, in each cin free form or in the form of a salt, to a method for the preparation and use of these compounds , E / Z isomers and tautomers, pesticides, whose active ingredient is selected from these compounds, E / Z isomers and tautomers, and a method for the preparation and use of these compositions, intermediates, in free form or in the form of a salt, for the preparation of these compounds, and where appropriate, their tautomers, in free form or in the form of a salt, and to a method for the preparation and use of these intermediates and their tautomers.
2. 2. A compound of the formula (I) according to claim 1, in free form.
3. 3. A compound of the formula (I) according to claim 1, wherein Ax and K1 are phenyl.
4. 4. A compound of the formula (I) according to claims 1 to 3, wherein: v2 is -alkyl of 1 to 6 carbon atoms-iNR ^ R ^, -C (= X) -R7a, -CO -alkyl of 9 to 20 carbon atoms, -alkyl of 1 to 6 carbon atoms -O-alkyl of 1 to 6 carbon atoms -O-alkyl of 1 to 6 carbon atoms, -Cñ20 (C = 0) - alkyl of 1 to 6 carbon atoms, -CH20 (C = 0) -alkenyl of 2 to 6 carbon atoms, -CH20 (C = 0) -alkynyl of 2 to 6 carbon atoms, C (= S) O- alkenyl of 2 to 6 carbon atoms, -C (= S) 0-alkynyl of 2 to 6 carbon atoms, -C (= S) S-alkyl of 1 to 6 carbon atoms, -C (= S) S -alkenyl of 2 to 6 carbon atoms, -C (= S) S-alkynyl of 2 to 6 carbon atoms, -C (= 0) S-alkyl of 1 to 6 carbon atoms, -C. { = 0) S-alkenyl of 2 to 6 carbon atoms, -C (= 0) S-alkynyl of 2 to 6 carbon atoms, -C (= S) NR1XR12, -C (= O) NR10OR13 -CH20-alkenyl of 2 to 6 carbon atoms, -CH20-alkynyl of 2 to 6 carbon atoms, -CH20-haloalkenyl of 2 to 6 carbon atoms, or -CH20-haloalkynyl of 2 to 6 carbon atoms.
5. 5. A compound of the formula (I) according to claims 1 to 4, wherein nx is 2, 3, or 4, and n2 is 1 or 2.
6. 6. A pesticidal composition comprising at least one compound of the formula (I) according to the claim 1 as an active ingredient, either in free form or in the form of an agrochemically acceptable salt, and at least one adjuvant.
7. 7. A method for pest control, which comprises applying a composition of claim 6 to the pests or their habitat.
8. 8. A method according to claim 7 for the control of insects and members of the order Acariña.
9. 9. A method for preparing a composition of claim 6 which contains at least one adjuvant, and comprises the intimate mixing and / or grinding of the active ingredient with the adjuvants.
10. The use of a compound of the formula (I) according to claim 1, either in free form or in the form of an agrochemically acceptable salt, for preparing a composition of claim 6.
11. 11. The use of a composition of claim 6 for pest control.
12. 12. The use of claim 11 for the protection of propagation material of plants.
13. 13. A method of claim 7 for protecting the plant propagation material, which comprises the treatment of the propagation material or the location for growing the propagation material.
14. 14. The plant propagation material that is treated according to the method described in claim 13. SUMMARY The compounds of the formula: where: A? and ^ 2 each independently represent one of the other, an aryl or heteroaryl radical; and A1 where appropriate, is substituted with the substitute-te (R3a) nX and A2, where appropriate, with the substituent (R3b) n2; nx and n2 are independently of each other, 0, 1, 2, 3, or 4; and any of: R3a and R3b, independently of one another, are, for example, halogen, alkyl of 1 to 6 carbon atoms, alkynyl of 2 to 4 carbon atoms, haloalkyl of 1 to 6 carbon atoms, haloalkynyl of 2 to 4 carbon atoms, alkoxy of 1 to 6 carbon atoms, haloalkoxy of 1 to 6 carbon atoms, alkenyloxy of 2 to 6 carbon atoms, alkynyloxy of 2 to 6 carbon atoms, or haloalkenyloxy of 2 to 6; and R2 is R2a; R2a is, for example-alkyl of 1 to 6 carbon atoms-NR ^ R ^, -CO-alkyl of 9 to 20 carbon atoms, alkyl of 1 to 6 carbon atoms-O-alkyl 'of 1 to 6 atoms carbon-O-alkyl of 1 to 6 carbon atoms, or CH20 (C = 0) alkyl of 1 to 6 carbon atoms; or at least one of the radicals R3a or R3b is -CRs = CR5R14f -NRiiRw -C (= 0) CN, -C (= 0) C (= 0) O-alkyl of 1 to 6 carbon atoms, -CR7 = NOR10 or a 5- or 6-membered heteroaryl ring linked by a carbon atom; R2 is R2a or R2b, wherein R2a is as defined hereinabove; and R 2b is, for example, hydrogen, -OH, alkenyl of 1 to 6 carbon atoms, or alkoxy of 1 to 6 carbon atoms; R 14 is, for example, hydrogen, halogen, alkyl of 1 to 6 carbon atoms, or haloalkyl of 1 to 6 carbon atoms; X is O or S; p is 0, 1, or 2; R5 is independently H or alkyl of 1 to 2 carbon atoms; R6 is, for example, independently H, alkyl of 1 to 8 carbon atoms, or cycloalkyl of 3 to 6 carbon atoms; R7 is, for example, H, alkyl of 1 to 8 carbon atoms, alkenyl of 2 to 8 carbon atoms, or haloalkyl of 1 to 8 carbon atoms; R8 is, for example, alkyl of 1 to 8 carbon atoms, alkenyl of 1 to 8 carbon atoms, or haloalkyl of 1 to 8 carbon atoms; R9 is alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 4 carbon atoms, or aryl; R10 is H, alkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, phenyl, or benzyl; R n and R 2"are, for example, independently of one another, H, alkyl of 1 to 6 carbon atoms, or phenyl; and where applicable, the possible E / Z isomers, mixtures of E / Z isomers, and / or tautomers thereof, in free form or in the form of agrochemically acceptable salt, can be used as agrochemical active ingredients, and can be prepared in a known way. * * * * *