MXPA99011168A - Organic compounds - Google Patents

Abstract

The invention relates to fluoroalkene carboxylic acid derivatives of general formula (I), in which R1 and R2 are hydrogen (independently of each other), or alkyl, a group of formula (II), cycloalkyl, alkenyl or alkynyl, which are optionally substituted;R3 is hydrogen, fluorine, or methyl;m is 0, 1, 2, 3, 4 or 5;n is 0 or 1;X is oxygen or NR4 and R4 is hydrogen or C1-C6-alkyl or benzyl, which are optionally substituted. The invention also relates to a method for their production, to insecticides containing the new fluoroalkene carboxylic derivatives as active agent, and their use against harmful insects and acarians.

Description

ORBANT COMPOUNDS The present invention relates to novel fluoroalkancarboxylic acid derivatives, to processes for their preparation, to insecticidal compositions comprising the novel fluoroalkancarboxylic acid derivatives as active compounds, and to the use of novel fluoroalkancarboxylic acid derivatives to control harmful insects and mites. The present invention provides compounds of the formula where RS and R2, independently of one another, are hydrogen, - or alkyl, a group H "\, aryl, cycloalkyl, alkenyl, or alkynyl, which are substituted or unsubstituted, R3 is hydrogen, fluorine, or methyl; is O, 1, 2, 3, 4, 0 5, n is 0 or 1, - X is oxygen or NR4, and R4 is hydrogen or alkyl of 1 to 6 carbon atoms, or benzyl, which are substituted or unsubstituted, and if appropriate, its possible E / Z isomers, mixtures of E / Z isomers, and / or tautomers, in each case in free form or in salt form, with the proviso that a) R3 is not hydrogen or fluorine, yyn are not both 0 if X is oxygen, and Rx and R2, independently of each other are hydrogen or unsubstituted or substituted alkyl, alkenyl, cycloalkyl, aryl, or heteroaryl, b) R3 is not hydrogen or fluorine, and m and n are not both 0, if R4 is hydrogen, and Rx and R2, independently of each other, are hydrogen or unsubstituted or substituted alkyl, aryl, or heteroaryl, c) m is not 0, 1, or 2, and R4 is h hydrogen, alkyl, or haloalkyl, if one of the radicals R 6 R 2 is 4-alkylsulfonyloxyphenyl, 4-haloalkylsulfonyloxyphenyl, or 4-haloalkoxysulfonyloxyphenyl, which may or may not bear additional substituents, and the other radical is substituted or unsubstituted phenyl; and d) m is not 0, 1, or 2, and R4 is not hydrogen, alkyl, or haloalkyl, and n is not 0, if one of the radicals Rx and R2 is 4-perhaloalkoxyphenyl, which may or may not bear additional substituents, and the other is substituted or unsubstituted phenyl, a process for the preparation and use of these compounds, E / Z isomers, and tautomers; pesticides whose active compound is selected from these compounds, E / Z isomers, and tautomers; and a process for the preparation and use of these compositions; intermediates, and if appropriate, their possible E / Z isomers, mixtures of E / Z isomers, and / or tautomers, in free form or in salt form, for the preparation of these compounds, if appropriate tautomers, in free form or in salt form, of these intermediaries; and a process for the preparation and use of these intermediaries and their tautomers. Preferred groups of the compounds of the formula (I) are - taking into account the conditions mentioned above - those where R? And R2 independently from each other are hydrogen or alkyl, cycloalkyl, alkenyl, or alkynyl, which are substituted or unsubstituted, R3 is hydrogen, fluorine, or methyl, m is 0, 1, 2, 3, 4, or 5; n is 0 or 1, X is oxygen or NR4, and R4 is hydrogen or alkyl of 1 to 6 carbon atoms or unsubstituted or substituted benzyl; where RL is hydrogen or unsubstituted or substituted alkyl, alkenyl, alkynyl, or cycloalkyl, R2 is hydrogen, or unsubstituted or substituted aryl or heteroaryl, R3 is hydrogen, fluorine, or methyl, m is 0, 1, 2, 3, 4, or 5; n is 0 or 1, X is oxygen or NR4, and R4 is hydrogen or alkyl of 1 to 6 carbon atoms or unsubstituted or substituted benzyl; and where R? Y ^ / independently of one another, are H or aryl, which are substituted or unsubstituted, R3 is hydrogen, fluorine, or methyl, m is 0, 1, 2, 3, 4, or 5; n is 0 or 1, X is oxygen or NR4, and R4 is hydrogen or alkyl of 1 to 6 carbon atoms unsubstituted or substituted, or benzyl. The general terms used in the above definitions of the substituents of R17 R2, R3, and R4 are defined as follows below: Halogen is fluorine, chlorine, bromine, or iodine, in particular fluorine, chlorine, or bromine, especially fluorine or chlorine , and in particular chlorine. Alkyl is a straight or branched chain alkyl radical having from 1 to 20 carbon atoms, which may be unsubstituted or mono- or poly-substituted. R and R2 as alkyl groups are preferably straight or branched chain alkyl radicals having from 1 to 8 carbon atoms, and particularly preferably, alkyl radicals having from 1 to 4 carbon atoms. Suitable substituents of R- and R2 as alkyl groups are hydroxyl, halogen, alkoxy, haloalkoxy, alkoxyalkoxy, thioalkyl, halothioalkyl, alkylsulfinyl, alkylsulfonyl, alkylsulfonyloxy, alkylcarbonyl, dialkylamino, pyrrolidino, piperidino, morpholino, alkoxycarbonyl, alkylcarbonyloxy, cycloalkyl, aryl, aryloxy, thioaryl, arylsulfonyl, arylsulfonyloxy, arylcarbo-nyl, or heteroaryl, wherein the aryl or heteroaryl groups on the other hand can be mono- or poly-substituted by halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, thioalkyl, Nitro, cyano, phenoxy, halofenoxyl, thiophenyl, or halothiophenyl. Alkyl radicals which are present as alkyl groups in the substituents of R-j and R2 preferably have from 1 to 4 carbon atoms. These alkyl radicals are particularly preferably methyl or ethyl radicals. Examples of R- | _ and R2 as alkyl groups are methyl, ethyl, normal propyl, isopropyl, normal butyl, isobutyl, secondary butyl, tertiary butyl, normal pentyl, 1-methylbutyl, 2,2-dimethylpropyl, isopentyl, normal hexyl. , 2-methylpentyl, 3-methylpentyl, 1,3-dimethylbutyl, 2-ethylbutyl, normal heptyl, normal octyl, iso-octyl, nonyl, decyl, undecyl, dodecyl, hexadecyl, and octadecyl. Preferred substituents of R-j and R2 as alkyl groups are hydroxyl, halogen, alkoxy, haloalkoxy, alkoxyalkoxy, thioalkyl, halothioalkyl, alkylsulfinyl, alkylsulfonyl, alkylsulfonyloxy, alkylcarbonyl, dialkylamino, pyrrolidino, piperidino, morpholino, alkoxycarbonyl, alkylcarbonyloxy, cycloalkyl. , wherein phenyl, phenoxy, thiophenyl, phenylsulfonyl, phenylsulfonyloxy, benzoyl, and pyridyl may be substituted by halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, thioalkyl, nitro, or cyano. The mono- or poly-substitution of a radical R-j_ or R2 is in particular a mono- to tetra-substitution, preferably a mono- to di-substitution, and in a particularly preferable way a monosubstitution, wherein R- and R2 in particular, as lower alkyl radicals, such as methyl or ethyl, can be perhalogenated, in particular perfluorinated, in the case of a halogen substitution. In the case of a polysubstitution, the respective substituents may be identical or different. Aryl is phenyl or naphthyl, preferably phenyl. Heteroaryl means aromatic radicals that have or 6 ring members, and 1 or 2 heteroatoms, selected from the group consisting of nitrogen, oxygen, and sulfur. Examples of the heteroaryl radicals are pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, thiazolyl, pyridyl, pyridazinyl, pyrimidinyl, and pyrazinyl, wherein the radicals R- | _ and R2 as heteroaryl radicals are in each case attached for a carbon atom, and if appropriate, a benzene ring can be condensed to the radicals. Preferred heteroaryl radicals are pyridyl, pyrimidinyl, quinolyl, furyl, and thienyl. The aryl radicals and the heteroaryl radicals may be unsubstituted or mono- or poly-substituted by halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, thioalkyl, halothioalkyl, alkylsulfonyloxy, haloalkylsulfonyloxy, haloalkoxy-sulfonyloxy, nitro, cyano, benzoyl, phenyl, phenoxy- it, thiophenyl, trialkylsilyl, benzyloxy, alkylamino, dialkylamino, pyrrolidino, piperidino, morpholino, anilino, cycloalkylalkoxy, or halocycloalkylalkoxy, heteroaryl or heteroaryloxy, wherein the benzoyl, phenyl, phenoxy, thiophenyl, benzyloxy, anilino, heteroaryl, and heteroaryloxy radicals as substituents on their part may be mono-poly-substituted by halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, thioalkyl, nitro, cyano, phenoxy, halofenoxyl, thiophenyl, halothiophenyl, cycloalkylalkoxy, or halocycloalkylalkoxy. Alkyl groups that are present as, or in, the substituents of R-j and R 2, such as aryl or heteroaryl groups, preferably have from 1 to 4 carbon atoms. These alkyl groups are particularly preferably methyl or ethyl groups. "Alkenyl" means straight or branched chain alkenyl radicals having from 3 to 20, preferably from 3 to 8 carbon atoms, and particularly preferably alkenyl radicals having from 3 to 5 carbon atoms, which may be unsubstituted or mono- or poly-substituted by halogen. "Alkenyl" preferably refers to those alkenyl radicals that are attached via a saturated carbon atom, ie, alkenyl radicals having an intermittent or terminal double bond. Examples of the alkenyl radicals are halyl, methallyl, but-2-en-1-yl, but-3-en-1-yl, pent-2-en-1-yl, pent-3-en-l- ilo, pent-4-en-l-yl, 2-methylbut-2-en-l-yl, hex-2-en-l-yl, hex-3-en-l-yl, hex-4-en- l -yl, hex-5-en-l-yl, hept-2-en-l-yl, oct-2-en-l-yl, and dec-2-en-1-yl. Particularly preferred alkenyl radicals are halyl and methallyl. Alkynyl means straight or branched chain alkynyl radicals having from 3 to 20, and preferably from 3 to 8 carbon atoms, and particularly preferably, alkynyl radicals having from 3 to 5 carbon atoms, which may be unsubstituted or mono- or poly-substituted by halogen. Alkynyl preferably refers to those alkynyl radicals that are attached via a saturated carbon atom, i.e., alkynyl radicals having an intermittent or terminal triple bond. Examples of the alkynyl radicals are propargyl, but-2-in-1-yl, but-2-yn-1-yl, pent-2-, -3-, or -4-in-1-yl, hex -2-, -3-, -4-, or -5-in-l-yl, hept-2-, -3-, -4-, -5-, or -6-in-l-yl, and oct-2-, -3-, -4-, -5-, - 6 -, 6 -7-in-l-yl. A particularly preferred alkynyl radical is the propargyl radical. Cycloalkyl means cycloalkyl radicals having from 3 to 7 carbon atoms, which may be unsubstituted or mono- or poly-substituted by halogen, alkyl, or haloalkyl, wherein the alkyl and haloalkyl radicals preferably contain from 1 to 4. carbon atoms, and particularly preferably from 1 to 2 carbon atoms. Examples of the cycloalkyl radicals are cyclopropyl, 2-methylcyclopropyl, cyclobutyl, cyclopentyl, 2-methylcyclopentyl, 3,4-dimethylcyclopentyl., cyclohexyl, 2-methylcyclohexyl, 4-methylcyclohexyl, 3,4-dimethylcyclohexyl, 2,4-dimethylcyclohexyl, and cycloheptyl. The above illustrated meaning of the general terms used in the definition applies, unless otherwise expressly reported, to the entire description herein. The present invention relates in particular to compounds of the formula (I) wherein, taking into account the conditions mentioned above, R-1 and R 2, independently of each other, are hydrogen; alkyl of 1 to 20 carbon atoms, which may be straight or branched chain, and which may be mono- to tetra-substituted by hydroxyl, halogen, alkoxy, haloalkoxy, alkoxyalkoxy. thioalkyl, halothioalkyl, alkylsulfinyl, alkylsulfonyl, arylsulfonyloxy, alkylcarbonyl, dialkylamino, pyrrolidino, piperidino, morpholino, alkoxycarbonyl, alkylcarbonyloxy, cycloalkyl, phenyl, naphthyl, phenoxy, naphthoxy, thiophenyl, thionaphthyl, phenylsulfonyl, naphthylsulfonyl, phenylsulfonyloxy, naphthylsulfonyloxy, benzoyl, naphthyl, heteroaryl, or heteroaryloxy having from 5 to 6 ring members and from 1 to 2 heteroatoms N, O, or S, wherein the aforementioned aryl or heteroaryl groups can be mono- or di-substituted by halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, thioalkyl, nitro, cyano, phenoxy, halofenoxyl, thiophenyl, or halothiophenol; alkenyl of 3 to 20 carbon atoms, which may be straight or branched chain, and may be mono- to tetra-substituted by halogen; alkynyl of 3 to 20 carbon atoms, which may be straight or branched chain, and may be mono- to tetra-substituted by halogen; cycloalkyl of 3 to 7 carbon atoms, which may be mono- or tetra-substituted by halogen, alkyl, or haloalkyl; phenyl or naphthyl, which may be mono- to tetra-substituted by halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, cycloalkylalkoxy, halocycloalkylalkoxy, thioalkyl, halothioalkyl, alkylsulfonyloxy, haloalkylsulfo-nyloxy, haloalkoxysulfonyloxy, alkylamino, dialkylamino, pyrrolidino, piperidino, morpholino, nitro, cyano, trialkylsilyl, phenyl, phenoxy, thiophenyl, benzoyl, benzyloxy, anilino, naphthyl, heteroaryl, or heteroaryloxy having from 5 to 6 ring members and from 1 to 2 heteroatoms N, O, or S, wherein the phenyl, phenoxy, thiophenyl, benzoyl, benzyloxy, amino, naphthyl, heteroaryl, and heteroaryloxy radicals as substitutes, on the other hand, can be mono- or di-substituted by halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, thioalkyl, nitro, cyano, phenoxy, thiophenyl, halothiophenyl, cycloalkylalkoxy, or halocycloalkylalkoxy; heteroaryl having 5 to 6 ring members and 1 to 2 heteroatoms N, O, or S, which may be mono- to tetra-substituted by halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, cycloalkylalkoxy, halocycloalkylalkoxy, thioalkyl, halothioalkyl, alkylamino, dialkylamino, pyrrolidino, piperidino, morpholino, nitro, cyano, trialkylsilyl, phenyl, phenoxy, thiophenyl, benzoyl, benzyloxy, anilino, naphthyl, heteroaryl, or heteroaryloxy having from 5 to 6 ring members, and from 1 to 2 heteroatoms, N, O, or S, wherein the phenyl, phenoxy, thiophenyl, benzoyl, benzyloxy, anilino, naphthyl, heteroaryl, or heteroaryloxy radicals as substituents, on the other hand, may be mono- or di-substituted by halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, thioalkyl, nitro, cyano, phenoxy, thiophenyl, halothiophenyl, cycloalkylalkoxy, halocycloalkylalkoxy; R3 is hydrogen, fluorine, or methyl; m is 0, 1, 2, 3, 4, or 5; n is 0 or 1; and X is oxygen or NR¿¡. , wherein R 4 is hydrogen, alkyl of 1 to 4 carbon atoms which may be mono- or poly-substituted by halogen, alkoxy of 1 to 4 carbon atoms, or dialkyl of 1 to 4 carbon-amino atoms, or is benzyl which may be mono- or poly-substituted by halogen, alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, nitro, or cyano. Preference is given to the compounds of the formula (I) wherein, taking into account the conditions mentioned above, R-j_ and R 2, independently of one another, are hydrogen, alkyl of 1 to 8 carbon atoms, which can be be straight chain or branched, or may be mono- or di-substituted by hydroxyl, halogen, alkoxy of 1 to 4 carbon atoms, haloalkoxy of 1 to 4 carbon atoms, alkoxyalkoxy of 1 to 4 carbon atoms, thioalkyl of 1 to 4 carbon atoms, halotioalkyl of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms-sulfinyl, alkyl of 1 to 4 carbon atoms-sulfonyl, alkyl of 1 to 4 carbon atoms-sulfonyloxy, alkyl of 1 to 4 carbon atoms-carbonyl, dialkyl of 1 to 4 carbon atoms-amino, pyrrolidino, piperidino, morpholino, alkoxy of 1 to 4 carbon atoms-carbonyl , alkyl of 1 to 4 carbon atoms-carbonyl-xyl, cycloalkyl of 3 to 6 carbon atoms, phenyl, naphthyl, phenoxy, naphthoxy, thiophenyl, thionaphthyl, phenylsulfonyl, naphthylsulfonyl, phenylsulfonyloxy, naphthylsulfonyloxy, benzoyl, naphthoyl, heteroaryl, or heteroaryloxy having 5 to 6 ring members, and 1 to 2 heteroatoms N, O, or S, wherein the aforementioned aryl or heteroaryl groups can be mono- or di-substituted by halogen, 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, thioalkyl of 1 to 4 carbon atoms, nitro, cyano, phenoxy, halofenoxyl, thiophenyl , or halothiophenyl; alkenyl of 3 to 8 carbon atoms which may be straight or branched chain, and may be mono- or di-substituted by halogen; alkynyl of 3 to 8 carbon atoms which may be straight or branched chain, and may be mono- or di-substituted by halogen; cycloalkyl of 3 to 7 carbon atoms which may be mono- or di-substituted by halogen, alkyl of 1 to 4 carbon atoms, or haloalkyl of 1 to 4 carbon atoms; phenyl or naphthyl, which may be mono- or di-substituted by halogen, 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 carbon, cycloalkyl of 3 to 6 carbon atoms-alkoxy of 1 to 4 carbon atoms, halo-cloalkyl of 1 to 4 carbon atoms-alkoxy of 1 to 4 carbon atoms, thioalkyl of 1 to 4 carbon atoms, halotioalkyl from 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms-sulfonyloxy, haloalkyl of 1 to 4 carbon atoms-sulfonyloxy, haloalkoxy of 1 to 4 carbon atoms-sulfonyloxy, alkyl of 1 to 4 carbon atoms- amino, dialkyl of 1 to 4 carbon atoms-amino, pyrrolidino, piperidino, morpholino, nitro, cyano, trialkyl of 1 to 4 carbon atoms-silyl, phenyl, phenoxy, thiophenyl, benzoyl, benzyloxy, anilino, naphthyl, heteroaryl, or heteroaryloxy having 5 to 6 ring members, and 1 to 2 heteroatoms N, 0, or S, wherein the phenyl, phenoxy, thiophenyl, benzoyl, benzyloxy, anilino, naphthyl, heteroaryl, and heteroaryloxy radicals as substituents on the other hand can be mono- or di-substituted by halogen, 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, thioalkyl of 1 to 4 carbon atoms, nitro, cyano, phenoxy, thiophenyl, halotiophene-nyl, cycloalkyl of 3 to 6 carbon atoms-alkoxy of 1 to 4 carbon atoms, or halocycloalkyl of 3 to 6 carbon atoms-alkoxy of 1 to 4 carbon atoms, heteroaryl having 5 to 6 ring members, and 1 to 2 heteroatoms N, O, or S, which may be mono- or di-substituted by halogen, 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, cycloalkyl of 3 to 6 carbon atoms-alkoxy of 1 to 4 carbon atoms, halocycloalkyl of 3 to 6 carbon-alkoxy atoms of 1 to 4 carbon atoms, thioalkyl of 1 to 4 carbon atoms, halotioalkyl of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon-amino atoms, dialkyl of 1 to 4 carbon atoms -amino, pyrrolidino, piperidino, morpholino, nitro, cyano, trialkyl of 1 to 4 carbon atoms-silyl, phenyl, phenoxy, thiophenyl, benzoyl, benzyloxy, anilino, naphthyl, heteroaryl, or heteroaryloxy having from 5 to 6 members of the ring, and from 1 to 2 heteroatoms N, O, or S, wherein the phenyl, phenoxy, thiophenyl, benzoyl, benzyloxy, anilino, naphthyl, heteroaryl, and heteroaryloxy radicals as substituents, may themselves be mono- or di- -substituted by halogen, 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, thioalkyl of 1 to 4 carbon atoms, nitro, cyano, phenoxy, thiophenyl, halothiophenyl, cycloalkyl of 3 to 6 carbon atoms alkoxy of 1 to 4 carbon atoms, or halocycloalkyl of 3 to 6 carbon atoms-alkoxy of 1 to 4 carbon atoms, R3 is hydrogen, fluorine, or methyl, m is 0, 1, 2, 3, or 4, n is 0 or 1, and X is oxygen or NR4, wherein R4 is hydrogen, alkyl of 1 to 4 carbon atoms which it may be mono- to di-substituted by halogen, alkoxy of 1 to 4 carbon atoms, or dialkyl of 1 to 4 carbon atoms-amino, or is benzyl which may be mono-di-substituted by halogen, alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, nitro, or cyano. The preferred meanings defined above of the radicals R-j_, R2. R3. and 4 are applied in a manner analogous to the subgroups of the compounds of the formula (I) defined above. Among the compounds of the formula (I), preference is also given to those where a) R3 is hydrogen; b) m is 0, 1, 2, 3, 0 4, particularly preferably 1 or 4; c) n is 0; d) R4 is hydrogen; e) 'R' and R2 are as defined above, R is hydrogen, m is 0, 1, 2, 3, or 4, n is O or l, and X is oxygen or NH; f) R-i and R2 are as defined above, R3 is hydrogen, m is 1, or 4, n is 0, and X is oxygen or NH; g) R - [_ is as defined above, R3 is hydrogen, and R2 is a group: wherein alk is methyl or ethyl, and the phenyl ring is substituted or unsubstituted. Particularly preferred individual compounds are the compounds of the formula (I), wherein R3 is hydrogen, Y a) R-j_ is hydrogen, R 2 is hydrogen, X is oxygen, is 1, and n is 0; b) R-j_ is methyl, R 2 is methyl, X is oxygen, m is 1 and n is 0; C) R-j is methyl, R 2 is phenyl, X is oxygen, m is 1, and n is 0; d) R -] _ is methyl, R 2 is trifluoromethylphenyl, X is oxygen, m is 1, and n is 0; e) R- is methyl, R2 is 4-nitrophenyl, X is oxygen, m is 1, and n is 0; f) R-j is methyl, R 2 is tertiary-4-butyl phenyl, X is oxygen, m is 1, and n is 0; g) R-L is phenyl, R 2 is phenyl, X is oxygen, m is 1, and n is 0; h) R-j_ is hydrogen, R2 is phenyl, X is oxygen, m is 1, and n is 0; i) R- | _ is phenyl, R 2 is benzyl, X is oxygen, m is 1, and n is 0; j) R-j_ is ethyl, R 2 is 4-chlorophenyl, X is oxygen, m is 1, and n is 0 k) R- | _ is hydrogen, R 2 is methyl, X is NH, m is 1, and n is 0; 1) R-, is methyl, R 2 is methyl, X is NH, m is 1, and n is 0; m) R-j_ is methyl, R 2 is phenyl, X is NH, m is 1, and n is 0; n) R-j_ is methyl, R2 is 3-trifluoromethylphenyl, X is NH, m is 1, and n is 0; o) R-, is methyl, R 2 is 4-tertiary butyl-phenyl, X is NH, m is 1, and n is 0; P) R- is phenyl, R 2 is phenyl, X is NH, m is 1, and n is 0; q) R-, is hydrogen, R2 is phenyl, X is oxygen, is 1, and n is 0; r) R-, is phenyl, R 2 is benzyl, X is NH, m is 1, and n is 0; s) R- | _ is ethyl, R 2 is 4-chlorophenyl, X is NH, m is 1, and n is 0; t) R-j_ is hydrogen, R 2 is hydrogen, X is NH, m is 1, and n is 1; u) R-j_ is methyl, R 2 is methyl, X is NH, m is 1, and n is 1; v) R- | _ is methyl, R2 is phenyl, X is NH, m is 1, and n is 1; w) R- | _ is methyl, R2 is 3-trifluoromethylphenyl, X is NH, m is 1, and n is 1; x) R-j_ is methyl, R2 is 4-tertiary butyl-phenyl, X is NH, m is 1, and n is 1; y) R-j_ is phenyl, R 2 is phenyl, X is NH, m is 1, and n is 1; z) R- | _ is hydrogen, R 2 is phenyl, X is oxygen, m is 1, and n is 1; aa) R-L is phenyl, R 2 is benzyl, X is NH, m is 1, and n is 1; or bb) R-1 is ethyl, R 2 is 4-chlorophenyl, X is NH, m is 1, and n is 1. The present invention also provides a process for the preparation of a compound of the formula (I), which understands a) preparing a compound of the formula (I), wherein n is 0, and R-j_, R2, R3, X, and m are as defined above in the formula (I), by the reaction of a compound of the formula wherein R3 and m are as defined in formula (I), and Y2 is Cl, Br, or OS02 -alkyl, with a compound of the formula / HX-N: ("I) \ where R- > , R2, and X are as defined in the formula (I) b) preparing compounds of the formula (I), wherein n is 0, and X is NR4, and RL, R2, R3, Y m are as defined in the formula (I), by the reaction of a compound of the formula wherein R3, R4 and are as defined in formula (I), with a compound of the formula / (V) \ wherein R ^ and R2 are as defined in formula (I); and c) preparing compounds of the formula (I), wherein n is 1, and R- | _, R2, R3, R4, X, and m are as defined in the formula (I), by the reaction of a compound of the formula wherein R and are as defined above in formula (I), with a compound of the formula in ~~ where Y? is Cl, Br, or 0S02 -alkyl, and X, R] _, and R2 are as defined above in formula (I). The starting materials of formulas (II) and (VI) are known, or can be prepared in a manner analogous to known processes. The starting materials of the formula (III) can be prepared in a manner known per se, by reacting a ketone of the formula (V) above with hydrazine, with a hydrazine which is monosubstituted by R according to the definition above, or with hydroxyl amine, wherein the ketones of the formula (V) in turn can be obtained by customary processes known for the preparation of ketones. The starting materials of the formula (II) can be obtained by the reaction of an acyl halide of the formula wherein Hal is chlorine or bromine, with a hydrazine which is monosubstituted by R4 according to the definition given above. The starting materials of the formula (VII) can be obtained by the reaction of a chloroacetyl halide, for example chloroacetyl chloride, with a compound of the formula (III) according to the above definition. The reaction of process a) is preferably carried out in an inert solvent which is free of hydroxyl groups, in the presence of an organic base, for example pyridine, 4-dimethyl aminopyridine, 4-pyrrolidinopyridine, lutidine, collidine, trialkyl amine , N, N-dialkyl aniline, or a non-nucleophilic bicyclic base, such as 1,4-diazabicyclo [2.2.2] octane (DABCO), 1,5-diazabicyclo [4.3.0] non-5-ene (DBN) or 1, 8-diazabicyclo- [5.4.0] undec-7-ene (1.5-5) (DBU). The reaction is generally carried out at temperatures from -30 ° C to + 70 ° C, preferably from -10 ° C to +50 ° C. Conveniently it is carried out in the presence of a solvent or a mixture of solvents which is inert to the reaction. Suitable for this purpose are, for example, aliphatic and aromatic hydrocarbons, such as benzene, toluene, xylenes, petroleum ether, hexane; halogenated hydrocarbons, such as chlorobenzene, methylene chloride, ethylene chloride, chloroform, carbon tetrachloride, tetra-chloroethylene; ethers and ether-type compounds, such as dialkyl ethers (diethyl ether, di-isopropyl ether, methyl tertiary butyl ether, etc.), anisole, dioxane, tetrahydrofuran; nitriles, such as acetonitrile, propionitrile; esters, such as ethyl acetate, propyl acetate, or butyl acetate; ketones, such as acetone, diethyl ketone, methylethyl ketone; and mixtures of these solvents with each other. However, the reaction can also be carried out in an excess of one of the aforementioned bases, or instead of the base, it is also possible to employ a second equivalent, or otherwise an even greater excess of the compound of the formula I. The reaction is carried out under atmospheric pressure; however, it is also possible to carry out the reaction under high or reduced pressure. The reaction of process b) is conveniently carried out in an inert solvent, at a temperature of 20 ° C to 150 ° C, preferably 40 ° C to 120 ° C, if appropriate in the presence of a catalytic amount of an acid , such as acetic acid or p-toluenesulfonic acid. Preferred inert solvents are lower alkanols, in particular methanol and ethanol. The reaction of process c) is conveniently carried out in an inert solvent, in the presence of a base, and if appropriate, in the presence of a catalyst, for example Nal or CsF, with the preferred inert solvents, polar aprotic solvents, such such as N, N-dimethyl formamide, dimethyl sulfoxide, dioxane, and tetrahydrofuran. Suitable bases are, in particular, pyridine, aminopyridine 4-dimethoxy, 4-pyrrolidi-nopyridine, lutidine, collidine, trialkine amine, N, N-dialkyl aniline, or a non-nucleophilic bicyclic base, such as 1,4-diazabicyclo [ 2.2.2] octane (DABCO), 1,5-diazabicyclo [4.3.0] non-Sine (DBN), or 1,8-diazabicyclo [5.4.0] undec-7-ene (1,5-5) ( DBU). The reactions described above and below are carried out in a manner known per se, for example in the absence, or if appropriate, in the presence of a suitable solvent or diluent, or a mixture thereof, as required, with cooling , - at room temperature, or with heating, for example on a temperature scale of about -80 ° C up to the boiling point of the reaction mixture, preferably from about -20 ° C to about + 150 ° C , and if required, in a closed container, under superatmospheric pressure, in an inert gas atmosphere, and / or under anhydrous conditions. In the examples, the particularly convenient reaction conditions are shown. The compounds of the formula (I) according to the invention are favorably tolerated by homoioterms, fish, and plants, and are active compounds useful in the field of pest control. The active compounds according to the invention are active, in particular, against insects and arachnids, as they are found in useful and ornamental plants in agriculture and horticulture, in particular in rice, cotton, vegetable and fruit plantations, and in forests. The compounds of formula (I) are particularly suitable for controlling insects in rice, fruit, and vegetable crops, in particular insects that damage plants, such as Aphis craccivora, Nilaparvata lugens and Nephotettix cincticeps. Other areas of use of the active compounds according to the invention are the protection of stored products and materials, and in the hygiene sector, in particular in the protection of pets and useful animals. The compounds of the formula (I) are active against all individual stages of development of normally sensitive but also resistant pest species. Its effect can be noticed, for example, in the destruction of pests, either immediately, or only after some time has elapsed, for example during the ecdysis, or as a reduced rate of oviposition and / or hatching. The aforementioned animal pests include, for example, those mentioned in European Patent Application Number EP-A-736, 252. European Patent Application Number EP-A-736,252, therefore, is included as a reference in the present subject matter. of the invention. The compounds of the formula (I) are suitable, in particular, to be used as active compounds to control pests of the Homoptera order, and of the Acariña order. The compounds of the formula (I) are particularly suitable for controlling pests in cotton, vegetable, fruit, and rice crops, such as spider mites, aphids, butterfly and moth caterpillars, and rice leafhoppers. The control is directed mainly against spider mites, such as Panonychus ulmi, aphids, such as Aphis craccivora, moth and butterfly caterpillars, such as those of Heliothis vires-cens, and rice grasshoppers, such as, Nilaparvata lugens or Nephotettix cincticeps . The good pesticidal action of the compounds of the formula (I) according to the invention corresponds to a destruction index (mortality) of at least 50 to 60 percent of the pests mentioned. The activity of the compounds of the formula (I) according to the invention, and of the compositions comprising them, can be substantially extended, and can be adapted to the specific circumstances by the addition of other insecticides and / or acaricides. Suitable additives are, for example, representatives of the following classes of active compounds: organic phosphorus compounds, nitrophenols and derivatives, formamidines, ureas, carbamates, pyrethroids, chlorinated hydrocarbons, and preparations of Bacillus thuringiensis. The compounds of the formula (I) are used as such, or preferably, together with auxiliaries which are used in the art of the formulation, and according to the same, can be processed, for example, up to emulsifiable concentrates, solutions directly sprayable or dilutable, dilute emulsions, wettable powders, soluble powders, powders, granules, or encapsulations in polymeric substances, in a known manner. The methods of application, such as spraying, atomizing, dusting, spreading, or watering, as the compositions, are selected in accordance with the intended objectives and the prevailing conditions. The formulation, i.e., the agents, preparations, or compositions comprising an active compound (I), or combinations of these active compounds with other insecticides or acaricides, and if appropriate, a solid or liquid additive, are prepared in a manner known, for example by intimate mixing and / or milling of the active compounds with extenders, for example solvents, solid carriers, and if appropriate, surface-active compounds (surfactants). Suitable auxiliaries, such as solvents, solid carriers, surface-active compounds, non-ionic surfactants, cationic surfactants, anionic surfactants, and other auxiliaries in the compositions used according to the invention are, for example, the same as those described. in European Patent Application Number EP-A-736,252. The pesticidal preparations generally comprise from 0.1 to 99 percent, in particular from 0.1 to 95 percent of the active compound I, or from the combination of this active compound with other insecticides and / or acaricides, and from 1 to 99.9 percent, in particular from 5 to 99.9 percent of a solid or liquid auxiliary, wherein in general from 0 to 25 percent, in particular from 0.1 to 20 percent of the preparations can be surfactants (percent in each case means cent in weight). Although concentrated compositions are usually preferred as commercial products, the end user generally employs dilute preparations having a substantially lower concentration of the active compound. Typical usage concentrations are between 0.1 and 1,000 ppm, preferably between 0.1 and 500 ppm. The application concentrations per hectare are generally from 1 to 1,000 grams of the active compound per hectare, preferably from 25 to 500 grams per hectare. Preferred formulations have, in particular, the following composition (% = percent by weight): Emulsifiable concentrates: Active compound: from 1 to 90 percent, preferably from 5 to 20 percent. Surfactant: from 1 to 30 percent, preferably from 10 to 20 percent. Liquid vehicle: from 5 to 94 percent, preferably from 70 to 85 percent.

Powders; Active compound: from 0.1 to 10 percent, preferably from 0.1 to 1 percent. Solid vehicle: from 99.9 to 90 percent, preferably from 99.9 to 99 percent.

Concentrates in suspension: Active compound: from 5 to 75 percent, preferably from 10 to 50 percent. Water: from 94 to 24 percent, preferably from 88 to 30 percent. Surfactant: from 1 to 40 percent, preferably from 2 to 30 percent. Wettable powders: Active compound: 0.5 to 90 percent, preferably 1 to 80 percent. Surfactant: from 0.5 to 20 percent, preferably from 1 to 15 percent. Solid vehicle: from 5 to 95 percent, preferably from 15 to 90 percent. Granules: Active compound: from 0.5 to 30 percent, preferably from 3 to 15 percent. Solid vehicle: from 99.5 to 70 percent, preferably from 97 to 85 percent.

The preparations may also comprise other auxiliaries, such as stabilizers, for example non-epoxidized or epoxidized vegetable oils (for example, coconut oil, rape seed oil, or epoxidized soybean oil), defoamers, for example silicone oil, preservatives. , viscosity regulators, binders and / or viscosifiers, and also fertilizers or other active compounds to obtain special effects.

The following examples serve to illustrate the invention. They do not limit the invention. Temperatures are mentioned in degrees Celsius.

The Hl i 0.73 grams (10 millimoles) of acetone oxime are dissolved, and 1.01 grams (10 millimoles) of triethyl amine in 30 milliliters of anhydrous benzene. At 5-10 ° C, the solution is mixed for a period of 30 minutes and with vigorous stirring with 1.68 grams (10 millimoles) of 6,6-difluorohex-5-enoic acid chloride (DAHSCI), and the mixture is stirred at room temperature for another 10 hours, and then filtered through a glass suction filter, and the filtrate is concentrated using a rotary evaporator. The resulting crude product is separated by column chromatography on silica gel (ethyl acetate: isohexane = 20:80). This gives the compound of the title of nD20 = 1.6893.

Example H2 ~ 1.5 grams (7.6 millimoles) of benzophenone hydrazone are dissolved, and 0. 11 grams (7.6 millimoles) of triethyl amine in 30 milliliters of anhydrous benzene, and at 5-10 ° C, the solution is mixed with 1.29 grams (7.6 millimoles) of 6,6-difluoro-hex-5-enoic acid chloride ( DAHSCI) during a period of 30 minutes. The mixture is then stirred at room temperature for another 10 hours, and filtered through a glass suction filter, and the filtrate is concentrated using a rotary evaporator. The resulting crude product is separated by column chromatography on silica gel (ethyl acetate: isohexane = 20:80). This gives the title compound of a p.f. 70-71 ° C.

Example H3; 0.5 grams (10 millimoles) of hydrazine hydrate are added to 1.64 grams (10 millimoles) of 6,6-difluorohex-5-enoate methyl in 10 milliliters of methanol. The solution is heated under reflux in a water bath for 10 minutes, and then concentrated using a rotary evaporator. The residue is suspended in 20 milliliters of methylene chloride, and at 0 ° C, it is mixed with 0.445 grams (10 millimoles) of acetaldehyde, and then the mixture is stirred at room temperature for another 10 hours. , and the crude product is separated by silica gel column chromatography (methyl acetate: isohexane = 20:80) This gives the title compound of p.p.78-79 ° C.

Example H4: 3.6 grams (18.4 millimoles) of benzophenone hydrazone, and 1.85 grams (18.3 millimoles) of triethyl amine are dissolved in 50 milliliters of benzene, and the mixture is cooled to 5 ° C. With efficient stirring, 2.06 grams (18.2 millimoles) of chloroacetyl chloride are slowly added dropwise, so that the temperature can be maintained at 5 ° C to 10 ° C at all times. After the addition of chloroacetyl chloride, stirring is continued at room temperature for 14 hours. The mixture is filtered, and the filtrate is concentrated. The residue is washed with a small amount of isohexane: acetic acid = 80:20, filtered, and dried. This gives the title compound of a p.f. 92-93 ° C. A mixture of 1.7 grams (6.2 millimoles) of chloroacetylbenzophenone hydrazide, 0.93 grams (6.2 millimoles) of 6,6-difluorohex-5-enoic acid, 0.63 grams (6.2 millimoles) of triethyl amine, and 0.2 grams of Nal in 10 milliliters of dimethyl formamide are stirred at room temperature for 14 hours.

The reaction mixture is poured onto ice, the mixture is extracted with chloroform, and the extract is dried over NaSO4. The solvent is distilled, and the crude product is separated on silica gel (isohexane: ethyl acetate = 80:20). This gives the compound of the title nD20 = 1.5678.

Example H5; 0.5 grams (10 millimoles) of hydrazine hydrate are added to a solution of 0.9 grams (10 millimoles) of methyl glycolate in 10 milliliters of methanol. For 10 minutes, the solution is heated under reflux in a water bath, and then concentrated using a rotary evaporator. The residue is suspended in 10 milliliters of methanol and mixed with 0.58 grams (10 millimoles) of acetone, and then the mixture is stirred at room temperature for 10 hours. The methanol is evaporated, and the residue is then suspended in 20 milliliters of dichloromethane / -tetrahydrofuran. 1.5 grams (10 millimoles) of 6,6-difluorohex-5-enoic acid, 406 grams (10 millimoles) of DCC, and 0.1 grams of 4-dimethyl aminopyridine are added to this mixture, which is then stirred for 14 hours, and filtered through a glass suction filter, and the filtrate is concentrated using a rotary evaporator. The resulting crude product is purified by silica gel column chromatography (ethyl acetate: isohexane = 20:80). This gives the title compound of nD20 = 1.6768. In a manner similar to that described in Examples Hl to H5, it is possible to prepare the compounds of the formula (I) mentioned in Tables 1 to 20.

Table 1: Compounds of the formula Comp. No. Ri Physical Data 1. 01 H H 1.02 H CH3 1.03 H C2H5 1.04 H C3Ht-n 1.06 H C4H9-n 1. 09 H CIOGI21-? 1.10 H CHaC (CH3) 3 1.11 CH3 H 1.12 CH3 CH3 1.14 CH3 C ^ T-n 1.16 CH3 C4H9-n 1.17 CH3 C4rl9-t Comp. No. Ri R2 Physical Data 1. 18 CH3 CßHis-n 1.20 CH3 Cp2C (Cp3) 3 1.21 CH3 C6H5 1.22 CH3 C6H4-2-CI 1.23 CH3 C6H4-3-CI 1.24 CH3 C6H4-4-CI 1.25 CH3 C6H4-2-CF3 1 .27 CH3 C6H4-4 -CF3 1.28 CH3 C6H4-2-CN 1.29 CH3 C6H4-3-CN 1.30 CH3 C6H4-4-CN 1.31 CH3 C6H4-2-NO2 1.33 CH3 C6H4-4-NO2 1.34 CH3 C6H4-4-C6H5 1.35 CH3 C6H4-4- OC6H5 1.36 CH3 CβH4-4-C (CH3) 3 1.37 CH3 C6H4-4-OCF3 1.38 CH3 C6H4-4-COOC2H5 1.39 CH3 C6F5 1.40 CH3 -C6H2-3.4.5- (OCH3) 3 Comp. No. Ri Physical Data 1. 44 CeHs CF3 1. 50 CßHs cyclopropyl 1 .51 CßHs cyclopentyl 1.52 CßHs cyclohexyl 1. 54 C6H5 C6H -4-CI 1. 59 CßHs C6H4-4-OC6H5 Comp. No. Ri R2 Physical Data 1. 60 CßHs C6H4-4-C (CH3) 3 1.62 C6H4-4-CI CF3 1.63 C6H4-4-CI C2H5 1.64 C6H4-4-CI C3Ht-n 1.65 C6H4-4-CI C3H7-Í 1. 68 C6H4-4-CI CH2C6H5 1.69 C6H4-4-CI CH2C6H4-4-CH3 1.70 C6H4-4-CI C6H4-4-CI 1.71 C6H4-4-CI C6H4-4-OH 1.72 C6H4-4-CI C6H4- -CH3 1 .73 C6H4-4-C! C6H4-2-CI 1.74 C6H4-4-CI C6H4-4-Br 1.75 C6H4-4-CI 4-pyridyl 1.76 C6H4-4-CI CH4-4-OCH2-C6H4-3-CF3 1. 80 C2H5 -C6H4-4-CI Table 2: Compounds of the formula H O I II -_c. ^ cN c CH, I I F R, Comp. No. Ri R2 Physical Data 2. 01 H H 2.02 H CH3 2.03 H C2H5 2.05 H CsH ^ i 2.06 H C4H9-n 2. 09 H C? OH2? -n 2.10 H CH2C (CH3) 3 2.11 CH3 H 2.12 CH3 CH3 2.14 CH3 C3Ht-n 2. 17 CH3 C4H9-t 2.18 CH3 CeHis-n 2.20 CH3 CH2C (CH3) 3 Comp. No. Ri R_ Physical Data 2. 22 CH3 C6H4-2-CI 2. 23 CH3 C6H4-3-CI 2.24 CH3 C6H4-4-CI 2.25 CH3 C6H4-2-CF3 2. 27 CH3 C6H4-4-CF3 2. 28 CH3 C6H4-2-CN 2. 29 CH3 C6H4-3-CN 2. 30 CH3 C6H4-4-CN 2. 32 CH3 C6H4-3-NO2 2.33 CH3 C6H4-4-NO2 2. 36 CH3 CßH4-4-C (CH3) 3 2. 38 CH3 C6H4-4-COOC2H5 2.39 CH3 C6F5 2.40 CH3 C6H2-3.4? 5- (OCH3) 3 2. 41 CH3 Comp. No. R. R2 Physical Data 2. 44 C6Hs CF3 2.47 C6H5 C3H7-1 2.50 CßHs cyclopropyl 2.51 CßHs cyclopentyl 2.52 CßHs cyclohexyl 2. 60 C6Hs C6H4-4-C (CH3) 3 2.61 CßHs C6H4-4-OCF3 Table 3: Compounds of the formula Comp. No. i Physical Data 3. 01 H H 3.02 H CH3 3.04 H C3Ht-n 3.06 H C4H9-n 3.07 H C4H9-t 3. 10 H CH2C (CH3) 3 3.11 CH3 H 3.12 CH3 CH3 3.13 CH3 C2H5 - 3.14 CH3 C3Ht-n 3.16 CH3 C4H9-n 3.18 CH3 CßHis-n 3.20 CH3 CH2C (CH3) 3 Comp. No. Ri Physical Data 3. 44 C6Hs CF3 3. 50 CßHs! cyclopropyl 3.51 CßHs cyclopentyl 3.52 CßHs cyclohexyl 3. 60 CßHs C6H4-4-C (CH3) 3 3.61 CßHs C6H4-4-OCF3 Comp. No. Ri 2 Physical Data 3. 62 C6H4-4-CI CF3 3.64 C6H4-4-CI C3Ht-n 3.65 C6H4-4-CI C3H-7-? 3. 69 C6H4-4-CI CH2CßH4-4-CH3 3.70 C6H4-4-CI C6H4-4-CI 3.71 _ C6H4-4-CI C6H4-4-OH 3.72 C6H4-4-CI CH4-4-CH3 3.73 C6H4-4- CI C6H4-2-CI 3.74 C6H4-4-CI C6H4-4-Br 3.75 C6H4-4-CI 4-pyridyl 3.76 C6H4-4-CI CßH4-4-OCH2-C6H4-3-CF3 3. 80 C2H5 -C6H4-4-CI Table 4: Compounds of the formula Comp. No. R2 Physical Data 4. 1 H H 4.2 H CH3 no20 = 1.6869 4. 3 H C2H5 4.4 H C3Ht-n 4.5 H C3Ht- | 4.6 H C4H9-n 4. 10 H CH2C (CH3) 3 4.11 CH3 H 4.12 CH3 CH3 no20 = 1 6893 4. 13 CH3 C2H5 4.14 CH3 C3Ht-n 4.15 CH3 C3H7-i 4.16 CH3 C H9-n 4.18 CH3 CßHis-n 4.19 CH3 C? 0H2i-n Comp. No. Ri R2 Physical Data 4. 47 CßHs CSHT-I Oil 4. 48 CßHs C4H9-t no20 = 1.4850 4.50 CßHs cyclopropyl no20 = 1.5132 4. 51 CßHs cyclopentyl 4.52 CßHs ciciohexilo 4.53 CßHs CßHs no20 = 1 .5503 4. 54 CßHs C6H4-4-CI Oil 4. 55 CßHs C6H4-4-CF3 no22 = 1 .5130 4. 57 CßHs CßH4-4-NO2 amorphous 4. 60 CßHs C6H4-4-C (CH3) 3 4.61 CßHs CßH -4-OCF3 Comp. No. Ri R¡ Physical Data , no20 = 1.4709 4. 67 C6H4-4-CI C4H9-n 4. 69 C6H4-4-CI CH2C6H4-4-CH3 4.70 C6H4-4-CI C6H4-4-CI p.f. : 66-67 ° C 4. 71 C6H4-4-CI C6H4-4-OH 4.72 C6H4-4-CI CH4-4-CH3 4.73 C6H4-4-CI C6H4-2-CI 4.74 C6H -4-CI C6H4-4-Br 4.75 C6H4-4-CI 4-pyridyl no20 = 1.5575 4. 76 C6H4-4-CI C6H4-4-OCH2-C6H4-3-CF3 ' nD20 = 1.5131 4. 79 CßHs CH2C6H5 no20 = 1.6744 4. 80 C2H5 -C6H4-4-CI no20 = 1.6768 4. 81 CH3 CßH3-3,5- (CF3) 2 no20 = 1.4509 4. 82 cyclopropyl -C6Hr4-CI no20 = 1.6820 - Comp. No. Ri R2 Physical Data Comp. Ri Physical Data 26 .94 -CßHs C6H4-2-F nD = 1.5390 .95 -CßHs C6H3-2.4-F2 nD 26 = 1.5267.96 -CßHs C6H4-4-F no25 = 1.5343.97 -C6H4-4-F C6H4- 4-F pf : 55-57 ° C 22 .98 -CßHs CßH4-3-CF3 nD = 1.5143 .99 -CßH4-3-CF3 CßH4-3-CF3 no22 = 1.4831 .100 -CßHs C6H4-2-CI no22 = 1.5523 .103 -CβHs -C6H3-4-CI-3-NO2 p.f. : 72-75 ° C 4.104 -CßHs -C6H4-3-NO2 nD = 1.5615 4.105 -CßHs -C6H3-2.4-CI2 «22 = 1.5490 Comp. No. Ri R2 Physical Data 4. 106 -C6 ßHns -C6H4-4-S-C6H4-4-CI nD 2"3 = 1.5757 4. 107 -C6 6H < I5 no23 = 1.5058 4. 108 -C6H4-4- -C6H4-4-O-CH3 nD24 = 1.5578 OCH3 4. 109 - 4-46 ° C 4. 110 1.5045 4. 111 1.5000 4. 112 1.6060 Table 5: Compounds of the formula Comp. No. Ri Physical Data . 1 H H 5.2 H CH3 p.f .: 78-79 ° C . 3 H C2H5 5.5 H C3Ht-i 5.6 H C4H9-n . 9 H C? OH2? -n 5.10 H CH2C (CH3) 3 5.11 CH3 H 5.12 CH3 CH3 no20 = 1.7589 5.14 CH3 C3Ht-n 5.15 CH3 C3HH 5.16 CH3 C4H9-n 5.18 CH3 CβHi3-n Comp. No. Ri R2 Physical Data . CH3 CH2C (CH3) 3 5.21 CH3 C6Hs p.f. 64-66 ° C . 22 CH3 C6H4-2-CI p.f .: 79-82 ° C . 23 CH3 C6H4-3 . 67 -C6H4-4-CI C4H9-n 5.68 -C6H4-4-CI CH2C6H5 5.69 -C6H4-4-Cl CH2C6H4-4-CH3 5.70 -C6H4-4-CI -C6H4-4-CI p.f .: 114-116 ° C . 71 -C6H4-4-CI -C6H4-4-OH 5.72 -C6H4-4-CI -CßH4-2-CH3 5.73 -C6H4-4-CI -CßH4-2-CI 5.74 -C6H4-4-CI -C6H4-4 -Br 5.75 -C6H4-4-Cl 4-pyridyl pf: 144-148 ° C . 76 -C6H4-4-CI -C6H4-4-OCH2-C6H4-3-CF3 Resin Comp. No. Ri R2 Physical Data . 83 -CßHs cyclopropyl p.f.:80-82°C . 84-CH3 -CβH3-3.5- (CF3) 2 p.f .: 103-105 ° C . 85 -C6Hs -C6H4-4-F p.f.:77-78°C . 86 -C6H5 -C6H3-2.4-F2 p.f .: 109-110 ° C . 87 -CßHs -C6H4-4-F p.f.:99-101°C . 88 -C6H4-4-F -CßH4-4-F p.f.:76-77°C . 89 'X. p.f .: 130-132 ° C . 90 -CßHs -C6H4-3-NO2 p.f .: 102-106 ° C . 91 -CßHs -CßH4-3-CF3 p.f.:49-50°C . 92 -CßHs p.f.:81-82°C . 93 -CßH-3-CF3 p.f. : 62-63 ° C . 94 -C6H4-4-OCH3 -C6H4-4-OCH3 p.f. : 82-83 ° C . 95 -C6H4-4-0CH3 -CH2-C6H4-4-OCH3 p.f .: 123-124 ° C . 96 -CßHs -CßH4-2-CI p.f. : 69-70 ° C . 97 -CßHs -CßH3-2,4-C «2 p.f .: 117-118 ° C . 98 -C6H4-4-N (CH3) 2 -C6H4-4-N (CH3) 2 p.f .: 93-94 ° C . 99 -CßHs -C6H4-4-S-CßH4-4-CH3 p.f .: 112-113 ° C . 100 -CßHs no20 = 1.5510 Comp. Ri R2 Physical Data Table 6: Compounds of the formula Comp. No. Ri R2 Physical Data 6. 1 H H 6.2 H CH3 no20 = 1, 6815 6.3 H C2Hs 6.4 H C3H7-n 6.5 H CaHT-i 6.6 H C4H9-n 6. 9 H CioH? J-n 6.11 CH3 H 6.12 CH3 CH3 amorphous 6.14 CH3 CsHt-n Comp. No. Ri R2 Physical Data 6. 15 CH3 CaHT-i 6.16 CH3 C4H9-n 6. CH3 CH2C (CH3) 3 6.21 CH3 CßHs p.f. : 92-94 ° C 6. 22 CH3 CßH4-2-CI P.f .: 58-60 ° C 6. 23 CH3 b6H4-3-CI p.f .: 126-127 ° C 6. 24 CH3 C6H4-4-CI p.f .: 125-127 ° C 6. 25 CH3 CßH -2-CF3 p.f. : 62-64 ° C 6. CH3 C3H4-3-CF3 p.f. : 148-149 ° C 6. 27 CH3 C6H4-4-CF3 p.f. : 103-104 ° C 6. 28 CH3 C6H4-2-CN 6.29 CH3 C6H4-3-CN p.f. : 130-131 ° C 6. 30 CH3 C6H4-4-CN p.f .: 141-142 ° C 6. CH3 C6H4-2-NO2 p.f. : 81-84 ° C 6. 32 CH3 C6H4-3-NO2 p.f .: 150-152 ° C 6. 33 CH3 CßH4-4-NO2 p.f. : 147-149 ° C 6. 34 CH3 8. 18 CH3 C6H13-n 8.20 CH3 CH2C (CH3) 3 8.21 CH3 C6Hs 8.22 ^ CH3 C6H4-2-CI 8.24 CH3 C6H4-4-CI 8. 27 CH3 C6H4-4-CF3 8.28 CH3 C6H4-2-CN 8.29 CH3 C6H4-3-CN 8.30 CH3 C6H4-4-CN 8.31 CH3 C6H4-2-NO2 8.32 CH3 C6H4-3-NO2 8.33 CH3 C6H4-4-NO2 8.35 CH3 CßH4-4-OCßHs 8.36 CH3 C6H4-4-C (CH3) 3 8.37 CH3 C6H4-4-OCF3 8.39 CH3 C6F5 8.40 CH3 C6H2-3.4.5- (OCH3) 3 Comp. No. Ri R2 Physical Data 8. 42 CH3 = f \ ^ N 8. 48 C6H5 C4H9-t 8.49 C6H5 C4H9-n 8.50 CßHs cyclopropyl 8.51 CßHs cyclopentyl 8.52 CßHs cyclohexyl 8. 59 C6Hs C6H4-4-OCßH5 Comp. No. 'Ri R2 Physical Data 8. 60 CßHs CßH4-4-C (CH3) 3 8.62 C6H4-4-CI CF3 8.63 C6H4-4-CI C2H5 8.64 C6H4-4-CI C3Ht-n 8.65 C6H4-4-CI C3Ht-i - 8.67 C6H4-4-CI C4H9-n 8.69 C6H4-4-CI CH2CßH4-4-CH3 8.70 CßH4-4-C! C6H4-4-CI 8.71 C6H4-4-CI C6H4-4-OH 8.72 C6H4-4-C! CßH4-2-CH3 8.73 C6H4-4-CI C6H4-2-CI 8.74 C6H4-4-CI C6H4-4-Br 8.75 C6H4-4-CI 4-pyridyl 8.76 C6H4-4-CI C6H4-4-OCH2-C6H4- 3-CF3 • - 8.80 C2Hs -C6H4-4-CI- Table 9: Compounds of the formula Comp. No. R Physical Data 9. 01 H H 9.02 H CH3 9.04 H C3Ht-n 9.06 H C4H9-n 9. 10 H CH2C (CH3) 3 9.11 CH3 H 9.12 CH3 CH3 9.14 CH3 C ^ HT-? 9.15 CH3 C3Ht-i 9.16 CH3 C4H9-n 9. 20 CH3 CH2C (CH3) 3 Comp. No. Ri R2 Physical Data 9. 42 CH3 \ = / = s N 9. 50 CßHs cyclopropyl 9.51 CßH5 cyclopentyl 9.52 C6H5 cyclohexyl 9.55 C6Hs C6H4-4-CF3 9. 59 CßHs C6H4-4-OCßHs 9.60 CßHs C6H4-4-C (CH3) 3 9.61 CßHs C6H4-4-OCF3 Comp. No. Ri R2 Physical Data 9. 62 C6H4-4-CI CF3 9.63 C6H4-4-CI C2H5 9. 67 C6H4-4-C! C4H9-n 9. 69 C6H4-4-CI CH2CßH4-4-CH3 9.70 C6H4-4-CI C6H4-4-CI 9.71 C6H4-4-CI C6H4-4-OH 9.72 C6H4-4-CI CH4-4-CH3 9.73 C6H4-4-CI C6H4-2-Cl 9.74 C6H4-4-CI C6H4-4-Br 9.75 C6H4-4-CI 4-pyridyl 9.76 C6H4-4-CI -C6H4-4-OCH2-C6H4-3-CF3 9. 80 C2H5 -C6H4-4-CI Table 10: Compounds of the formula Comp. No. Ri Physical Data . 01 H H 10.02 H CH3 . 04 H C3H7-n 10.06 H C4H9-n . 10 H CH2C (CH3) 3 10.11 CH3 H 10.12 CH3 CH3 . 15 CH3 CsH ^ i 10.16 CH3 C4H9-n . 19 CH3 CioH? I-n Comp. No. Ri R2 Physical Data . 20 CH3 CH2C (CH3) 3 10.22 CH3 C6H4-2-CI 10.23 CH3 C6H4-3-CI 10.24 CH3 C6H4-4-CI . 27 CH3 C6H4-4-CF3 10.28 CH3 C6H4-2-CN 10.30 CH3 C6H4-4-CN 10.31 CH3 C6H4-2-NO2 10.32 CH3 C6H4-3-NO2 10.33 CH3 C6H4-4-NO2 . 36 CH3 C6H4-4-C (CH3) 3 10.37 CH3 C6H4-4-OCF3 10.38 CH3 C6H4-4-COOC2H5 10.39 CH3 * C6F5 10.40 CH3 C6H2-3.4.5- (OCH3) 3 . 41 CH3 Comp. No. Ri R2 Physical Data . 42 CH3 \ = f \ N . 46 C6H5 C3H n . 50 CßHs cyclopropyl 10.51 C6H5 cyclopentyl 10.52 CßHs cyclohexyl . 59 CßHs C6H4-4-OC6Hs 10.60 CßHs C6H4-4-C (CH3) 3 10.61 CßHs C6H4-4-OCF3 Table 11: Compounds of the formula Comp. No. Ri R2 Physical Data 11. 01 H H 11.02 H -CH3 11.04 H -CsH n 11.05 H -C3H7-11.06 H -C4H9-n 11. 09H -C? OH2.-n 11.10 H -CH2C (CH3) 3 11.11 CH3 H 11.12 CH3 -CH3 11.13 CH3 -C? Hs " 11. 14 CH3 -CaHT-n 11.15 CH3 -CaH i 11.16 CH3 -C4H9-n 11. 19 CH3 -C-ioH? I-n Comp. No. Ri Physical Data 11. 50 CßHs cyclopropyl 11.51 CßHs cyclopentyl 11.52 CßHs cyclohexyl 11. 55 CeHd -C6H4-4-CF3 11. 58 CßHs -CßH -4-CßHs 11.60 CßHs -C6H4-4-C (CH3) 3 11.61 CßHs -CßH4-4-OCF3 Comp. No. Ri R2 Physical Data 1 1.62 C6H4-4-CI -CF3 11.63 C6H4-4-CI -C2H5 11.64 C6H4-4-CI -CSHT-? 11 .65 C6H4-4-CI -C3H7-i 11.66 C6H4-4-CI -C4Hg-t 11.67 C6H4-4-CI -C4H9-n 11.68 C6H4-4-CI -CH2C6H5 11.69 C6H4-4-CI -CH2C6H4 -4-CH3 11.70 C6H4-4-CI -C6H4-4-CI 11 .71 C6H4-4-CI -C6H4-4-OH 11.72 C6H4-4-CI -CßH4-2-CH3 11.73 C6H4-4-CI -C6H4 -2-CI 11.74 C6H4-4-CI -C6H4-4-Br 11 .75 C6H4-4-CI 4-pyridyl 11 .76 C6H4-4-CI -C6H4-4-OCH2-C6H4-3-CF3 11. 80 C2H5 -C6H4-4-CI Table 1 2: Compounds of the formula Comp. No. RÍ R2 Physical Data 12. 01 H H 12.02 H CH3 12.03 H C2H5 12.04 H CsH n - 12.05 H CSHT-Í 12.06 H C4H9-n 12. 10 H CH2C (CH3) 3 12.11 CH3 H 12.12 CH3 CH3 12.13 CH3 C2H5 12.14 CH3 C3H ^ n 12.15 CH3 CSHT-Y 12.16 CH3 C4H9-n 12. CH 3 CH 2 C (CH 3) 3 Comp. No. Ri Physical Data 12. 22 CH3 C6H4-2-CI 12.23 CH3 C6H4-3-CI 12.24 CH3 C6H4-4-CI 12.26 CH3 C6H4-3-CF3 12.27 CH3 C6H4-4-CF3 12.28 CH3 C6H4-2-CN 12.29 CH3 C6H4-3-CN 12.30 CH3 C6H4-4-CN 12.31 CH3 C6H4-2-NO2 12.32 CH3 C6H4-3-NO2 12.33 CH3 C6H4-4-NO2 12. 36 CH3 C6H4-4-C (CH3) 3 12.37 CH3 C6H4-4-OCF3 12.38 CH3 C? H4-4-COOC2Hs 12.40 CH3 C6H2-3.4.5- (OCH3) 3 12. 41 CH3 Comp. No. Ri R_ Physical Data 12. 50 CßHs cyclopropyl 12.51 CßHs cyclopentyl 12.52 C6Hs cyclohexyl 12. 59 CßHs C6H4-4-OC6H5 12.60 CßHs C6H4-4-C (CH3) 3 12.61 CßHs C6H4-4-OCF3 Table 13: Compounds of the formula Comp. No. i R2 Physical Data 13. 01 H H 13.02 H CH3 13.04 H C3Ht-n - 13.06 H C4H9-n 13. 10 H CH2C (CH3) 3 13.11 CH3 H 13.12 CH3 CH3 13.14 CH3 CsH n 13.16 CH3 C4H9-n 13. 19 CH3 C? OH2i-n Comp. No. Ri Physical Data 13. 42 CH3 \ = / \ ^ N 13. 50 C6HS cyclopropyl 13.51 CßHs cyclopentyl 13.52 CßHs cyclohexyl 13.59 CßHs CßH4-4-OCßHs 13.60 CßHs C6H4-4-C (CH3) 3 13.61 CßHs CßH4-4-OCF3 Comp. No. Ri R2 Physical Data 13. 64 C6H4-4-CI CsH-rD 13.65 C6H4-4-CI C3HH 13.67 C6H4-4-CI C4H9-n 13.68 C6H4-4-C! CH2C6H5 13.69 C6H4-4-CI CH2C6H4-4-CH3 13.70 C6H4-4-CI C6H4-4-CI 13.71 C6H4-4-CI C6H4-4-OH 13.72 C6H4-4-CI CH4-4-CH3 13.73 C6H4-4- CI C6H4-2-CI 13.74 C6H4-4-CI C6H4-4-Br 13.75 C6H4-4-CI 4-p? Pd? Lo 13.76 C6H4-4-Cl C6H4-4-OCH2-C6H4-3-CF3 13. 78 H C6Hs 13.80 C2H5 -C6H4-4-CI Table 14: Compounds H | a formula Comp. No. Ri Physical Data 14. 01 H H 14.02 H CH3 14.04 H CsHr-n 14.06 H C4H9-n 14.08 H C6H? 3-n 14. 11 CH3 H 14.12 CH3 CH3 14.14 CH3 C3Ht-n 14. 18 CH3 CßHis-n 14.19 CH3 C? OH2i-n Comp. No. Ri Physical Data 14. 42 CH3 \ = \ sS- N 14. 50 CßHs cyclopropyl 14.51 CßHs cielopentilo 14.52 CßH5 ciciohexilo 14. 59 CßHs C6H4-4-OCßH5 14.60 C6H5 CßH4-4-C (CH3) 3 14.61 CßHs CßH4-4-OCF3 Comp. No. Ri R2 Physical Data 14. 62 C6H4-4-CI CF3 14.64 C6H4-4-CI C3Ht-n 14.65 C6H -4-CI C3H7-i 14.67 C6H4-4-CI C4H9-n 14.68 C6H4-4-CI CH2C6H5 14.69 C6H4-4-CI CH2C6H4- - CH3 14.70 C6H4-4-CI C6H4-4-C! 14.71 C6H4-4-CI C6H4-4-OH 14.72 C6H4-4-CI CH4-4-CH3 14.73 _ C6H4-4-CI C6H4-2-CI 14.74 C6H4-4-CI C6H4-4-Br 14.75 C6H4-4- CI 4- | pyridyl 14.76 C6H4-4-CI CßH4-4-OCH2-CßH4-3 'CF3 14. 80 C2Hs -C6H4-4-CI Table 1 5: Compounds of the formula Comp. No. R! R2 Physical Data . 01 H H 15.02 H CH3 15.03 H C2H5 15.04 H C3H7-n 15.05 H C3Ht-i 15.06 H C4H9-n . 10 H CH2C (CH3) 3 15.11 CH3 H 15.12 CH3 CH3 15.13 CH3 C2H5 15.14 CH3 C3Ht-n 15.15 CH3 C3HH 15.16 CH3 C4H9-n . CH 3 CH 2 C (CH 3) 3 Comp. No. Ri R2 Physical Data . 22 CH3 C6H4-2-CI 15.23 CH3 C6H4-3-CI "15.24 CH3 C6H4-4-CI . 27 CH3 C6H4-4-CF3 15.28 CH3 C6H4-2-CN 15.29 CH3 C6H4-3-CN 15.30 CH3 C6H4-4-CN 15.31 CH3 C6H4-2-NO2 15.32 CH3 C6H4-3-NO2 15.33 CH3 C6H4-4-NO2 15.35 CH3 C6H4-4-OC6Hs 15.36 CH3 C6H4-4-C (CH3) 3 15.37 CH3 C6H4-4-OCF3 15.39 CH3 C6Fs 15.40 CH3 C6H2-3.4.5- (OCH3) 3 . 41 CH3 Comp. No. Ri Physical Data . 44 C6Hs CF3 . 50 C6H5 cyclopropyl 15.51 CßHs cyclopentyl 15.52 CßHs cyclohexyl . 59 CßHs CßH4-4-OC6H5 15.60 CßHs C6H4-4-C (CH3) 3 15.61 CßHs C6H4-4-OCF3 Table 1 6: Compounds of the formula Comp. No. Physical Data 16. 01 H H 16.02"H CH3 16.04 H CsH n 16.05 H C3Ht-i 16.06 H C4H9-n 16. 09 H C? OH2? -n 16.11 CH3 H 16.12 CH3 CH3 16.14 CH3 CSHT-? 16.15 CH3 CsH i 16.16 CH3 C4H9-n 16. 19 CH3 C? OH2i-n Comp. No. Ri R2 Physical Data 16. 20 CH3 CH2C (CH3) 3 16.22 CH3 C6H4-2-CI 16.23 CH3 C6H4-3-CI 16.24 CH3 C6H4-4-CI 16.25 CH3 C6H4-2-CF3 16.26 CH3 C6H4-3-CF3 16.27 CH3 C6H4-4-CF3 16.28 CH3 C6H4-2-CN 16.29 CH3 C6H4-3-CN 16.30 CH3 C6H4-4-CN 16.31 CH3 C6H4-2-NO2 - 16.32 CH3 C6H4-3-NO2 16.33 CH3 C6H4-4-NO2 16. 36 CH3 C6H4-4-C (CH3) 3 16.37 CH3 C6H4-4-OCF3 16.38 CH3 C6H4-4-COOC2H5 16.40 CH3 C6H2-3.4.5- (OCH3) 3 16. 41 CH3 N Comp. No. Ri R2 Physical Data 16. 62 C6H4-4-CI CF3 16.63 C6H4-4-CI C2H5 16.64 C6H4-4-CI C3Hrn 16. 67 C6H4-4-CI C H9-n 16.68 CßH4-4-CI CH2C6H5 16.69 C6H4-4-CI CH2CßH4-4-CH3 16.70 C6H4-4-CI C6H4-4-CI 16.71 C6H4-4-CI C6H4-4-OH 16.72 C6H -4-CI CH4-4-CH3 16.73 C6H4-4-CI C6H4-2-CI 16.74 C6H4-4-CI C6H4-4-Br 16.75 C6H4-4-CI 4-pyridyl 16.76 C6H4-4-CI C6H4- 4-OCH2-C6H4-3-CF3 16. 80 CsHs -C6H4-4-CI Table 1 7: Compounds of the formula Comp. No. i Physical Data 17. 01 H H 17.02 H CH3 17.03 H C2H5 17.04 H C3Ht-n 17.05 H C3H7-i 17.06 H C H9-n 17. 10 H CH2C (CH3) 3 17.11 CH3 H 17.12 CH3 CH3 17.13 CH3 C2H5 17. 16 CH3 C4H9-n 17. 19 CH3? OH2i-n Comp. No. Ri Physical Data 17. 20 CH3 CH2C (CH3) 3 17.22 CH3 C6H4-2-CI 17.23 CH3 C6H4-3-CI 17. 27 CH3 C6H4-4-CF3 17.28 CH3 C6H4-2-CN 17.29 CH3 C6H4-3-CN 17.30 CH3 C6H4-4-CN 17.32 CH3 C6H4-3-NO2 17.33 CH3 C6H4-4-NO2 17. 36 CH3 C6H4-4-C (CH3) 3 17.37 CH3 C6H4-4-OCF3 17.38 CH3 C6H4-4-COOC2Hs 17.39 CH3 C6F5 17.40 CH3 ^ C6H2-3.4.5- (OCH3) 3 17. 41 CH3 -O-O Comp. No. Ri R2 Physical Data 18. CH3 CH2C (CH3) 3 18.22 CH3 C6H4-2-CI. ' -r G 18. 23 CH3 C6H4-3-CI 18.24 CH3 C6H4-4-CI 18. 27 CH3 C6H4-4-CF3 18.28 CH3 * C6H4-2-CN 18.29 CH3 C6H4-3-CN 18.30 CH3 C6H4-4-CN 18.31 CH3 C6H4-2-NO2 18. 33 CH3 C6H4-4-NO2 18.35 CH3 C6H4-4-OC6H5 18.36 CH3 CßH4-4-C (CH3) 3 88.37 CH3 C6H4-4-OCF3 18.38 CH3 C6H4-4-COOC2H5 18.39 CH3 C6F5 18.40 CH3 C6H2-3, 4.5- (0CH3) 3 18. 41 CH3 Comp. No. Ri Physical Data 18. 42 CH3 \ = / \ ^ N 18. 50 CßHs cyclopropyl 18.51 C6H5 cyclopentyl 18. 52 CßHs cyclohexyl 18. 59 CßHs CβH4-4-OC6H5 18.60 CßHs CßH 4 -4 -C (CH 3) 3 Comp. No. Ri R2 Physical Data 18. 62 C6H4-4-CI CF3 18. 68 C6H4-4-CI CH2C6H5 18.69 C6H4-4-CI CH2C6H4-4-CH3 18.70 CβH4-4-CI CβH4-4-CI 18.71 CβH4-4-CI CßH4-4-OH 18.72 C6H4-4-CI CßH -2- CH3 18.73 C6H4-4-CI C6H4-2-CI 18.74 C6H4-4-CI C6H4-4-Br 18.75 C6H4-4-Cl 4-Pyridyl 18.76 C6H4-4-CI CßH4-4-OCH2-CßH -3- CF3 18. 80 CzHg -C6H4-4-CI Table 1 9: Compounds of the formula Comp. No. R. R2 X n Physical Data 19. 2 -CßHs -CßH5 NH 1 p.f .: 92-93 ° C 19. 8 -CßHs -CßHs O 1 amorphous 19. 12 -CßHs -CßH4-4-CI O 19.13 CH3 -CßH4-4-CI NH 0 19.15 CH3 -CβH4-4-CI NH 2 19.17 CH3 -CβH -4-CI NH 4 19.1 S CH3 -C6H4-4-C1 O 0 Comp. No. Ri R2 X n Physical Data 19. CH3 -C6H4-4-CI O1.19.21 CH3 -C6H4-4-CI O2 19.22 CH3 -C6H4-4-CI O3 19.23 CH3 -C6H4-4-CI O 4 19.24 CH3 -CβH4-4-CI O 5 19.25 -C6H4-4-C! -C6H4-4-CI NH 1 19.26 -CßH4-4-CI -CßH4-4-CI O 1 Table 20: Compounds of the formula Comp. No. Ri Physical Data . 2 -CßHs -CßHs NH 1 p.f .: 89-100 ° C .8-CgHs -CßHs O 1 no = 1.5530 20.10 -CßHs -CßHs O 3 Comp. No. Ri R2 X n Physical Data . 12 -CßHs -C6H4-4-CI O 5 20.13 CH3 -C6H4-4-CI NH 0,. . 14 CH 3 -C 6 H 4 -4-CI NH 1 20.15 CH 3 • -C 6 H 4 -4-CI NH 2 20.16 CH 3 -C 6 H 4 -4-CI NH 3 20.17 CH 3 -C 6 H 4 -4-CI NH 4 20.18 CH 3 -C 6 H 4 -4-CI NH 5 20.19 CH3 - -C6H4-4-CI O 0 20.20 CH3 -C6H4-4-CI O 1 20.21 CH3 -C6H4-4-CI O2 20.22 CH3 -C6H4-4-CI O 3 20.23 CH3 -C6H4-4-CI O 4 20.24 CH3 -C6H4-4-CI O 5 20.25 -CßH4- 4-CI -C6H4-4-CI NH 1 20.26 -C6H4-4-CI -CßH4-4-CI O 1 Biological Examples Example Bl; Ovicidal action on heliothis virescens The eggs of Heliothis virescens, which have been deposited on filter paper, are briefly immersed in an acetonic / aqueous test solution comprising 400 ppm of the active compound to be tested. After the test solution is surface dried, the eggs are bated in Petri dishes. After 6 days, the percentage of hatching rate of the eggs is evaluated in comparison with the untreated control batches (% reduction in hatching). In this test, the compounds according to Tables 1 to 20 are very effective against Heliothi s virescens. Compounds 4.80, 4.53, 4.78, 4.12, 4.21, 4.79, 4.02, 4.36, 4.26, 5.76, 5.77, 5.53, 5.21, 5.78, 5.02, 5.12, 5.79, 5.36, 5.26, 5.80, 6.53, 6.21, 6.78, 6.79, 6.12, 6.02, 6.36, 6.26, and 6.80, in particular, exhibit an activity of more than 80 percent.

Example B2: Action against Nila.pa.rva.ta lugens The rice plants are treated with an aqueous emulsion spray liquor comprising 400 ppm of the active compound. After the spray coating is surface dried, rice plants are populated with larvae of the second and third seedlings of Nilaparva ta lugens. 21 days later, the test is evaluated. The percentage reduction in the population (percentage of activity) is determined by comparing the number of surviving grasshoppers in the treated plants, with that in the untreated plants. In this test, the compounds of Tables 1 to 20 are very effective against Nilaparvata lugens. Compounds 4.80, 4.53, 4.78, 4.12, 4.21, 4.79, 4.02, 4.36, 4.26, 5.76, 5.77, 5.53, 5.21, 5.78, 5.02, 5.12, 5.79, 5.36, 5.26, 5.80, 6.53, 6.21, 6.78, 6.79, 6.12, 6.02, 6.36, 6.26, and 6.80, in particular, exhibit an activity of more than 80 percent.

Example B3; Activity against larvae of Diahrotica bal teata Corn seedlings are sprayed with an aqueous emulsion spray liquor comprising 400 ppm of the active compound. After the spray coating is surface dried, the corn seedlings are populated with 10 larvae of the second Diabrotica Jbalteata seedling, and placed in a plastic container. Six days later, the test is evaluated. The percentage reduction in the population (percentage of activity) is determined by comparing the number of dead larvae in the treated plants, with that in the untreated plants. In this test, the compounds in Tables 1 to 20 are very effective against Diabroti ca bal teata. Compounds 4.80, 4.53, 4.78, 4.12, 4.21, 4.79, 4.02, 4.36, 4.26, 5.76, 5.77, 5.53, 5.21, 5.78, 5.02, 5.12, 5.79, 5.36, 5.26, 6.53, 6.21, 6.78, 6.79, 6.12, 6.02, 6.26, and 6.80, in particular, exhibit an activity of more than 80 percent.

Example B; Activity against Tetranychus urticae Young bean plants are populated with a mixed population of Tetranychus urticae, and one day later, they are sprayed with an aqueous emulsion spray liquor comprising 400 ppm of the active compound. Subsequently the plants are incubated for 6 days at 25 ° C, and then evaluated. The percentage reduction in the population (% activity) is determined by comparing the number of eggs, larvae, and dead adults in the treated plants, with that in the untreated plants. In this test, the compounds of Tables 1 to 20 are very effective against Tetranychus urticae. Compounds 4.80, 4.53, 4.78, 4.12, 4.21, 4.79, 4.02, 4.36, 4.26, 5.76, 5.77, 5.53, 5.21, 5.78, 5.02, 5.12, 5.79, 5.36, 5.26, 5.80, 6.53, 6.21, 6.78, 6.12, 6.02, 6.36, 6.26, and 6.80, in particular, exhibit an activity of more than 80 percent.

Example B5; Activity against caterpillars of Spodoptera li ttoralis Young soybean plants are sprayed with an aqueous emulsion spray liquor comprising 400 ppm of the active compound. After the spray coating is surface dried, the soybean plants are populated with 10 caterpillars in the third Spodoptera li ttoralis moult, and are introduced into a plastic container. Three days later the test is evaluated. The percentage of reduction in the population, and the percentage of reduction in the damage by feeding (percentage of activity), are determined by comparing the number of dead caterpillars and the damage by feeding, respectively, in the treated plants, with those in the untreated plants. In this test, the compounds of Tables 1 to 20 are very effective against Spodoptera li ttoralis. Compounds 4.80, 4.53, 4.12, 4.21, 4.36, 5.77, 5.53, 5.21, 5.78, 5.79, 5.36, 5.26, 5.80, 6.53, 6.21, 6.12, 6.02, 6.36, 6.26, and 6.80, in particular, exhibit an activity of more than 80 percent.

Example B6; Activity against caterpillars of Plutella xylostella The young cabbage plants are sprayed with an aqueous emulsion spray liquor comprising 400 ppm of the active compound. After the spray coating is surface dried, the cabbage plants are populated with 10 caterpillars in the third seedling of Plutella xylostella, and are introduced into a plastic container. Three days later the test is evaluated. The percentage of reduction in the population, and the percentage of reduction in feeding damage (percentage of activity), are determined by comparing the number of dead caterpillars and the damage by feeding, respectively, in the treated plants, with those in the plants not treated. In this test, the compounds of Tables 1 to 20 are very effective against Plutella xylostella. Compounds 4.80, 4.53, 4.78, 4.12, 4.21, 4.79, 4.02, 4.36, 4.26, 5.77, 5.53, 5.78, 5.36, 5.26, 5.80, 6.53, 6.21, 6.78, 6.12, 6.02, and 6.80, in particular, exhibit a activity of more than 80 percent.

Example B7; Activity against ApJiis craccivora Pea seedlings are infected with Aphis craccivora, and subsequently sprayed with a spray liquor comprising 400 ppm of the active ingredient, and incubate at 20 ° C. Three and six days later, respectively, the test is evaluated. The percentage of reduction in the population (percentage of activity) is determined by comparing the number of remains of dead leaves in the treated plants, with that in the untreated plants. In this test, the compounds of Tables 1 to 20 are very effective against Aphis craccivora. Compounds 4.80, 4.53, 4.78, 4.12, 4.21, 4.79, 4.36, 4.26, 5.77, 5.53, 5.78, 5.26, 5.80, 6.53, 6.21, 6.78, 6.12, 6.02, and 6.80, in particular, exhibit an activity of more than 80 percent.

Example B8; Activity against M? Zus persicae Pea seedlings are infected with Myzus persicae, and subsequently sprayed with a spray liquor comprising 400 ppm of the active compound, and incubated at 20 ° C.

Three and six days later, respectively, the test is evaluated.

The percentage reduction in the population (percentage of activity) is determined by comparing the number of dead aphids in the treated plants, with that in the untreated plants.

In this test, the compounds of Tables 1 to 20 are very effective against Myzus persicae. The compounds 4.80, 4.53, 4. 78, 4.12, 4.21, 4.79, 4.36, 4.26, 5.21, 5.78, 5.26, 5.80, 6.53 6. 21, 6.78, 6.12, 6.02 and 6.80, in particular, exhibit an activity of more than 80 percent.

Example B9; Systemic action against M? Zus persicae Pea seedlings are infected with Myzus persicae, then the roots are placed in a spray liquor comprising 400 ppm of the active compound, and the seedlings are incubated at 20 ° C. Three and six days later, respectively, the test is evaluated. The percentage reduction in the population (percentage of activity) is determined by comparing the number of dead aphids in the treated plants, with that in the untreated plants. In this test, the compounds of Tables 1 to 20 are very effective against Myzus persicae. Compounds 4.80, 4.53, 4.78, 4.12, 4.21, 4.79, 4.02, 4.36, 5.21, 5.78, 5.02, 5.12, 6.21, 6.78, 6.79, and 6.80, in particular, exhibit an activity of more than 80 percent.

Example B10; Ovial / larvicidal action in Heliothis virescens The eggs of Heliothis virescens, which have been deposited on cotton, are sprayed with an aqueous emulsion spray liquor comprising 400 ppm of the active compound. After 8 days, the percentage of hatching index of the eggs and the index of survival of the caterpillars are evaluated in comparison with the untreated control batches (% reduction in the population). In this test, the compounds of Tables 1 to 20 are very effective against Heliothis virescens. Compounds 4.80 4.53, 4.78, 4.12, 4.21, 4.79, 4.02, 4.36, 4.26, 5.76, 5.77, 5.53, 5.21, 5.78, 5.02, 5.12, 5.79, 5.36, 5.26, 5.80, 6.53, 6.21 , 6.78, 6.79, 6.12, 6.02, 6.36, 6.26 and 6.80, in particular, exhibit an activity of more than 80 percent.

Example Bll: Ovicidal activity against Tetranychus urticae Young bean plants are populated with female Tetranychus urticae, which is removed again after 24 hours. The plants that are populated with eggs are sprayed with an aqueous emulsion spray liquor comprising 400 ppm of the active compound. Subsequently the plants are incubated at 25 ° C for 6 days, and then evaluated. The percentage reduction in the population (% activity) is determined by comparing the number of eggs, larvae, and dead adults in the treated plants, with that in the untreated plants. In this test, the compounds of Tables 1 to 20 are very effective against Tetranychus urticae. Compounds 4.53, 4.78, 4.12, 4.21, 4.79, 4.02, 4.36, 4.26, 5.76, 5.77, 5.53, 5.21, 5.78, 5.12, 5.79, 5.36, 5.26, 5.80, 6.53, 6.21, 6.78, 6.12, 6.02, 6.36, 6.26 and 6.80, in particular, exhibit an activity of more than 80 percent.

Example B12; Activity against Panonychus ulmi (resistant to OP and Carb.) The apple seedlings are populated with adult females of Panonychus ulmi. After 7 days, the infected plants are sprayed to the point of runoff with an aqueous emulsion spray liquor comprising 400 ppm of the compound to be tested, and grown in a greenhouse. After 14 days, the test is evaluated. The percentage reduction in the population (percentage of activity) is determined by comparing the number of spider mites killed in the treated plants, with that in the untreated plants. In the above test, the compounds of Tables 1 to 20 are very effective. Compounds 4.53, 4.78, 4.12, 4.21, 4.79, 4.36, 4.26, 5.76, 5.77, 5.53, 5.21, 5.78, 5.12, 5.79, 5.36, 5.26, 5.80, 6.53, 6.21, 6.78, 6.12, 6.02, 6.36, 6.26 and 6.80, in particular, exhibit an activity of more than 80 percent.

Claims (19)

1. CLAIMS A compound of the formula: where R? And R2 / independently of one another, are hydrogen; or alkyl, a group N == v 'aryl, cycloalkyl, alkenyl, or alkynyl, which are substituted or unsubstituted; R3 is hydrogen, fluorine, or methyl; m is 0, 1, 2, 3, 4, or 5; is 0 or 1; X is oxygen or NR4, and R4 is hydrogen or alkyl of 1 to 6 carbon atoms, or benzyl, which are substituted or unsubstituted, and if appropriate, their possible E / Z isomers, mixtures of E / Z isomers, and / or tautomers, in each case in free form or in salt form, with the proviso that a) R3 is not hydrogen or fluorine, and m and n are not both 0 if X is oxygen, and Rx and R2, independently of one another are hydrogen or unsubstituted or substituted alkyl, alkenyl, cycloalkyl, aryl, or heteroaryl; b) R3 is not hydrogen or fluorine, and m and n are not both 0, if R4 is hydrogen, and Rx and R2, independently of one another, are hydrogen or unsubstituted or substituted alkyl, aryl, or heteroaryl; c) m is not 0, 1, or 2, and R 4 is hydrogen, alkyl, or haloalkyl, if one of the radicals R? or R2 is 4-alkylsulfonyloxyphenyl, 4-haloalkylsulfonyloxyphenyl, or 4-haloalkoxysulfonyloxyphenyl, which may or may not carry additional substituents, and the other radical is substituted or unsubstituted phenyl; and d) m is not 0, 1, or 2, and R4 is not hydrogen, alkyl, or haloalkyl, and n is not 0, if one of the radicals Rx and R2 is 4-perhaloalkoxyphenyl, which may or may not bear additional substituents, and the other is substituted or unsubstituted phenyl.
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: Rx and R2, independently of one another, are hydrogen; alkyl of 1 to 20 carbon atoms, which may be straight or branched chain, and which may be mono- to tetra-substituted by hydroxyl, halogen, alkoxy, haloalkoxy, alkoxyalkoxy, thioalkyl, halothioalkyl, alkylsulfinyl, alkylsulfonyl, arylsulfonyloxy, alkylcarbonyl , dialkylamino, pyrrolidino, piperidino, morpholino, alkoxycarbonyl, alkylcarbonyloxy, cycloalkyl, phenyl, naphthyl, phenoxy, naphthoxy, thiophenyl, thionaphthyl, phenylsulfonyl, naphthylsulfonyl, phenylsulfonyloxy, naphthylsulfonyloxy, benzoyl, naphthyl, heteroaryl, or heteroaryloxy having from 5 to 6 members of the ring and from 1 to 2 heteroatoms N, O, or S, wherein the aforementioned aryl or heteroaryl groups can be mono- or di-substituted by halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, thioalkyl, nitro, cyano , phenoxy, halofenoxyl, thiophenyl, or halotiophene; alkenyl of 3 to 20 carbon atoms, which may be straight or branched chain, and may be mono- to tetra-substituted by halogen; alkynyl of 3 to 20 carbon atoms, which may be straight or branched chain, and may be mono- to tetra-substituted by halogen; cycloalkyl of 3 to 7 carbon atoms, which may be mono- or tetra-substituted by halogen, alkyl, or haloalkyl; phenyl or naphthyl, which may be mono- to tetra-substituted by halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, cycloalkylalkoxy, halocycloalkylalkoxy, thioalkyl, halothioalkyl, alkylsulfonyloxy, haloalkylsulfo-nyloxy, haloalkoxysulfonyloxy, alkylamino, dialkylamino, pyrrolidino, piperidino, morpholino, nitro, cyano, trialkylsilyl, phenyl, phenoxy, thiophenyl, benzoyl, benzyloxy, anilino, naphthyl, heteroaryl, or heteroaryloxy having from 5 to 6 ring members and from 1 to 2 heteroatoms N, O, or S, wherein the phenyl, phenoxy, thiophenyl, benzoyl, benzyloxy, amino, naphthyl, heteroaryl, and heteroaryloxy radicals as substitutes, on the other hand, can be mono- or di-substituted by halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, thioalkyl, nitro, cyano, phenoxy, thiophenyl, halothiophenyl, cycloalkylalkoxy, or halocycloalkylalkoxy; heteroaryl having 5 to 6 ring members and 1 to 2 N heteroatoms, O, or S, which may be mono- to tetra-substituted by halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, cycloalkylalkoxy, halocycloalkylalkoxy, thioalkyl, halothioalkyl, alkylamino, dialkylamino, pyrrolidino, piperidino, morpholino, nitro, cyano, trialkylsilyl, phenyl, phenoxy, thiophenyl, benzoyl, benzyloxy, anilino, naphthyl, heteroaryl, or heteroaryloxy having from 5 to 6 ring members, and from 1 to 2 heteroatoms, N, O, or S, wherein the phenyl, phenoxy radicals , thiophenyl, benzoyl, benzyloxy, anilino, naphthyl, heteroaryl, or heteroaryloxy as substituents, on the other hand can be mono- or di-substituted by halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, thioalkyl, nitro, cyano, phenoxy, thiophenyl, halotiophenyl, cycloalkylalkoxy, halocycloalkylalkoxy; R3 is hydrogen, fluorine, or methyl; m is 0, 1, 2, 3, 4, or 5; n is O or 1; and X is oxygen or NR4, wherein R4 is hydrogen, alkyl of 1 to 4 carbon atoms which may be mono- or poly-substituted by halogen, alkoxy of 1 to 4 carbon atoms, or dialkyl of 1 to 4 carbon atoms. carbon-amino, or is benzyl which may be mono- or poly-substituted by halogen, alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, nitro, or cyano .
4. 4. A compound of the formula (I) according to any of claims 1 or 2, wherein Rx and Rj, independently of one another, are hydrogen, or unsubstituted or substituted alkyl, cycloalkyl, alkenyl, or alkynyl, R3 is hydrogen, fluorine, or methyl, is 0, 1, 2, 3, 4, or 5; n is 0 or 1, X is oxygen or NR4, and R4 is hydrogen or alkyl of 1 to 6 carbon atoms or unsubstituted or substituted benzyl.
5. A compound of the formula (I), according to claim 1 or 2, wherein RL is hydrogen, or unsubstituted or substituted alkyl, alkenyl, alkenyl, or cycloalkyl, R2 is hydrogen, or unsubstituted or substituted aryl or heteroaryl , R3 is hydrogen, fluorine, or methyl, m is 0, 1, 2, 3, 4, or 5, and n is 0 or 1, X is oxygen or NR4, and R4 is hydrogen, or alkyl of 1 to 6 carbon atoms. carbon or benzyl unsubstituted or substituted.
6. 6. A compound of the formula (I) according to claim 1 or 2, wherein Rx and Ej, independently of one another, are hydrogen, or unsubstituted or substituted aryl, R3 is hydrogen, fluorine, or methyl, m is 0, 1, 2, 3, 4, or 5, and n is 0 or 1, X is oxygen or NR4, and R4 is hydrogen, or alkyl of 1 to 6 carbon atoms or unsubstituted or substituted benzyl.
7. 7. A compound of the formula (I) according to any of claims 1 to 5, wherein R3 is hydrogen, and R1 R2, R4, m, n, and X are as defined.
8. 8. A compound of the formula (I) according to any of claims 1 to 5, wherein m is 0, 1, 2, 3, or 4, and Rx, R2, R3, R4, n, and X are how they were defined.
9. 9. A compound of the formula (I) according to any of claims 1 to 5, wherein m is 1 or 4, and R1 f R2, R3, R4, n, and X are as defined.
10. 10. A compound of the formula (I) according to any of claims 1 to 5, wherein n is 0, and R17 R2, R3, R4, m and X are as defined.
11. 11. A compound of the formula (I) according to any of claims 1 to 5, wherein n is 0, and m is 1 or 4, and Ri, R2, R3, R4 and X are as defined.
12. 12. A compound of the formula (I) according to any of claims 1 to 5, wherein R3 is hydrogen, n is 0, and m is 1 or 4, X is NH or oxygen, and Rx and R2 are as they defined
13. 13. A process for the preparation of a compound as defined in claim 1, in the formula (I), which comprises a) preparing a compound of the formula (I), wherein n is 0, and Rx, R2 , R,, X, and m are as defined above in formula (I), by the reaction of a compound of the formula wherein R. and m are as defined in formula (I), and Y2 is Cl, Br, or OSCA-alkyl, with a compound of the formula / HX-N: (III) \ where R-, R2, and X are as defined in the formula (i: b) preparing compounds of the formula (I), wherein n is 0, and X is NR4, and R-j_, R2, 3 / Y "-» »are as defined in the formula (I), by reacting a compound of the formula wherein R3, R4 and m are as defined in formula I), with a compound of the formula , R1 / (V) \ wherein R-j_ and R2 are as defined in formula (I); And c) preparing compounds of the formula (I), wherein n is 1, and R-1, R 2, R 3, R 4, X, and m are as defined in the formula (I), by the reaction of a compound of the formula wherein R3 and m are as defined above in formula (I), with a compound of the formula wherein Yj_ is Cl, Br, or 0S02 -alkyl, and X, R- | _, and R2 are as defined above in formula (I).
14. 14. A pesticide that contains in addition to auxiliaries and inert vehicles, at least one compound of the formula (I) according to claim 1, as active substance. ~ Í5.
15. A process for the preparation of a pesticide according to claim 14, which comprises mixing a compound of the formula (I) according to claim 1, with auxiliaries and inert carriers.
16. 16. A method for controlling pests, which comprises applying a compound of the formula (I) as described in claim 1, or a composition as described in claim 14, to the pests or their habitat.
17. 17. The use of a compound of the formula (I) as described in claim 1, or if appropriate, an E / Z isomer or tautomer thereof, in free form or in the form of an agrochemically usable salt, for the preparation of a composition as described in claim 14.
18. 18. A method according to claim 16 for protecting the propagation supply of plants, which comprises treating the propagation supply or the location where the propagation supply is planted. .
19. 19. The use of a compound of the formula (I) as described in claim 1, or of a composition as described in claim 14, for controlling pests.