Animal pests destroy growing and harvested crops and attack wooden dwelling and commercial structures, causing large economic loss to the food supply and to property.

While a targe number of pesticidal agents are known, due to the ability of target pests to develop resistance to said agents, there is an ongoing need for new agents for com- bating animal pests. In particular, animal pests such as insects, acaridae and/or arach- nids are difficult to be effectively controlled.

It is therefore an object of the present invention to provide compounds having a good pesticidal activity, especially against difficult to control insects, arachnids and acaridae.

DD 55 956, DD 99 794 and FR 1567021 describe [1,2, 4]-triazolo [1,5-a] pyrimidines of the generai formula (A) having a pharmaceutical activity, wherein R,, R4 may be hydrogen, lower alkyl, alkoxyalkyl, halogen, aryl or arylalkyl, R2 may be hydrogen, halogen, lower alkyl, lower alkenyl, arylalkyl or aryl and R3 may be an optionally substituted amino group, wherein the substituents are selected-inter alia-from alkyl, cycloalkyl, alkenyl, hydroxylalkyl, alkylaminoalkyl, alkoxyalkyl, aryl, arylalkyl, heteroaryl or heteroaralkyl.

WO 03/039259 describes substituted s-1,2, 4-triazolo [1, 5-a] pyrimidine compounds hav- ing fungicidal activity.

So far no 6-halogeno- [1, 2,4] triazolo [1,5-a] pyrimidines have been described, which are useful for combating animal pests, especially for combating insects, arachnids and/or acaridae.

It has been found that 6-halogeno- [1, 2,4] triazolo [1, 5-a] pyrimidines of the general for- mula (I)

wherein X is halogen; Ri is hydrogen, halogen, OH, CN, C1-Cio-alkyl, C1-C1o-haloalkyl, Ci-Cio-alkoxy, C,- C6-alkoxy-Ci-C6-alkyl, C1-C4-alkoxy-C1-C4-alkoxy, C1-C4-alkoxy-C1-C4-alkoxy-C1- C4-alkoxy, Ci-Cio-alkylthio, Ci-C1o-alkylsulfinyl, C1-C1o-alkylsulfonyl, Ci-Cio- alkylamino, di (C1-C10-alkyl) amino, C2-C10-alkenyl, phenyl, phenoxy, benzyloxy, C2-C10-alkenyloxy, C2-C10-alkynyloxy or C2-C1o-alkynyl, wherein C1-C10-alkylthio, C1-C10-alkylsulfinyl and C1-C10-alkylsulfonyl may be unsubstituted or partially or completely substituted with halogen and/or may carry a group selected from C1- C4-alkoxy, C1-C4-alkoxycarbonyl or COOH, in particular hydrogen, halogen, C1- C10-alkyl, C1-C10-haloalkyl, C1-C10-alkoxy, C1-C6alkoxy-C1-C6-alkyl, C1-C10- alkylthio, C1-C10-alkylsulfinyl, C1-C10-alkylsulfonyl, C1-C10-alkylamino, di(C1-C10- alkyl) amino, C2-C10-alkenyl or C2-C10-alkynyl ; R2 is C1-C1o-alkyl, C1-C10-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C3-C10-cycloalkyl, C2- C10-alkenyl or C2-Cio-alkynyl ; R3 is hydrogen, C1-C10-alkyl, C1-C10-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C10- alkylcarbonyl, Ci-Cio-alkoxycarbonyl or arylcarbonyl ; R4 is C3-C1o-cycloalkyl, phenyl, naphthyl, 3-to 7-membered heterocyclyl or a radical of the formula-A-R4a, it being possible for C3-C10-cycloalkyl, phenyl, naphthyl and 3-to 7-membered heterocyclyl to be unsubstituted or to carry 1,2 or 3 radicals which are selected, independently from each other, from the group consisting of halogen, cyano, nitro, hydroxy, C1-C10-alkyl, C1-C10-alkoxy, C1-C10-haloalkyl, C1- Cio-haloalkoxy, amino, C1-C10-alkylamino, di (C1-C10-alkyl) amino, Ci-C1o-alkylthio, C1-C10-alkylsulfinyl, C1-C10-alkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4- alkyl, phenyl, phenyl-C1-C4-alkoxy and phenyloxy, wherein the five last- mentioned radicals for their part may be unsubstituted or may carry one, two or three substituents which are selected, independently from each other, from the group consisting of C1-C4-alkyl, C1-C4-alkoxy and halogen,

and wherein heterocyclyl contains 1,2 or 3 heteroatoms selected, independently from each other, from the group consisting of oxygen, sulfur, nitrogen and a group NR, it being also possible for C3-Cio-cycloalkyl, phenyl and 3-to 7-membered hetero- cyclyl to be fused to a 5-to 7-membered saturated, unsaturated or aromatic car- bocyclic ring or to a 5-to 7-membered heterocyclic ring and said fused ring may be unsubstituted or may itself carry one, two, three, four, five or six substituents which are selected, independently from each other from the group consisting of halogen and C1-C4-alkyl ; wherein A is a C1-C6-alkylene chain which may comprise one heteroatom selected from the group consisting of oxygen and sulfur ; R4a is C3-Cio-cycloalkyl, phenyl, naphthyl or 3-to 7-membered heterocyclyl, it being possible for C3-C10-cycloalkyl, phenyl, naphthyl and 3-to 7-mem- bered heterocyclyl to be unsubstituted or to carry 1,2 or 3 radicals which are selected, independently from each other, from the group consisting of halogen, cyano, nitro, hydroxy, C1-C10-alkyl, Ci-C1o-alkoxy, Cl-C10- haloalkyl, Ci-C1o-haloalkoxy, amino, Ci-Cio-alkylamino, di (C,-C1o- alkyl) amino, C1-C10-alkylthio, C1-C10-alkylsulfinyl, C1-C10-alkylsulfonyl, C3- C8-cycloalkyl, C3-C8-cycloalkyl-C,-C4-alkyl, phenyl, phenyl-C1-C4-alkoxy and phenyloxy, wherein the five last-mentioned radicals for their part may be unsubstituted or may carry one, two or three substituents which are se- lected, independently from each other, from the group consisting of C1-C4- alkyl, C1-C4-alkoxy and halogen, and wherein heterocyclyl contains 1,2 or 3 heteroatoms selected, inde- pendently from each other, from the group consisting of oxygen, sulfur, ni- trogen and a group NR, it being also possible for C3-Cio-cycloalkyl, phenyl and 3-to 7-membered heterocyclyl to be fused to a 5-to 7-membered saturated, unsaturated or aromatic carbocyclic ring or to a 5-to 7-membered heterocyclic ring and said fused ring may be unsubstituted or may itself carry one, two, three, four, five or six substituents which are selected, independently from each other from the group consisting of halogen and C1-C4-alkyl ; and R5 is hydrogen, C1-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl ; and the agricultural acceptable salts thereof have a high pesticidal activity, especially against difficult to control insects, arachnids and/or acaridae.

Therefore, the present invention relates to the use of the compounds of formula I and of the salts thereof for combating animal pests and also to a method of combating ani- mal pests which comprises contacting the animal pests, their habit, breeding ground, food supply, plant, seed, soil, area, material or environment in which the animal pests are growing or may grow, or the materials, plants, seeds, soils, surfaces or spaces to be protected from animal attack or infestation with a pesticidally effective amount of at least one 6-halogeno- [1, 2, 4]-triazolo [1, 5-a]-pyrimidine of the general formula I and/or at least one agriculturally acceptable salt thereof.

The 6-halogeno- [1, 2, 4]-triazolo [1,5-a]-pyrimidine of the general formula I as defined herein and the agricultural acceptable salts thereof are particularly useful for combat- ing animal pests which are harmful to crops. Therefore the present invention also re- lates to the use of the compounds of the general formula I for protecting crops from attack or infestation by animal pests. Thus, the present invention provides a method for protecting crops from attack or infestation by animal pests which comprises contacting a crop with a pesticidally effective amount of a 6-halogeno- [1, 2, 4]-triazolo [1,5-a]- pyrimidine of the general formula I and/or at least one salt thereof.

The invention also relates to 6-halogeno- [1, 2,4] triazolo [1, 5-a] pyrimidine compounds of the general formula I wherein X, R', R2, R3 and R4 are as defined above provided that A in the radical A-R4a is a C2-C6-alkylene chain which is attached to the nitrogen atom via a secondary or tertiary carbon atom of the alkylen chain and said C2-C6-alkylene chain may comprise one heteroatom selected from the group consisting of oxygen and sulfur ; and to the agricultural useful salts thereof.

Furthermore, the invention relates to agricultural compositions, preferably in the form of directly sprayable solutions, emulsions, pastes oil dispersions, powders, materials for scattering, dusts or in the form of granules, which comprise at least one 6-halogeno- [1,2, 4] triazolo [1, 5-a] pyrimidine of the general formula I as defined above, admixed with one or more agronomically acceptable inert, solid or liquid carrier (s) and, if desired, at least one surfactant.

In the substituents, the compounds of the general formula I may have for a given con- stitution different spatial arrangement of the atoms, e. g. they may carry one or more

centers of chirality, in which case they are present as mixtures of stereoisomers, such as enantiomers or diastereomers. The present invention provides both the pure stereo- isomers, e. g. the pure enantiomes or diastereomers, and mixtures thereof.

Salts of the compounds of the formula I which are suitable for the use according to the invention are especially agricultural acceptable salts. They can be formed in a cus- tomary method, e. g. by reacting the compound with an acid of the anion in question.

Suitable agriculturally useful salts are especially the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, do not have any adverse effect on the action of the compounds according to the present invention, which are useful for combating harmful insects or arachnids. Thus, suitable cations are in particular the ions of the alkali metals, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, and of the transi- tion metals, preferably manganese, copper, zinc and iron, and also the ammonium ion which may, if desired, carry one to four C1-C4-alkyl substituents and/or one phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabu- tylammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri (Ci-C4-alkyl) sulfonium, and sulfoxonium ions, preferably tri (Ci-C4- alkyl) sulfoxonium.

Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, hy- drogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of C1-C4-alkanoic acids, preferably formate, acetate, propionate and bu- tyrate. They can be formed by reacting the compounds of the formulae la and lb with an acid of the corresponding anion, preferably of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.

The organic moieties mentioned in the above definitions of the variables are-like the term halogen-collective terms for individual listings of the individual group members.

The prefix Cn-Cm indicates in each case the possible number of carbon atoms in the group.

The term halogen denotes in each case fluorine, bromine, chlorine or iodine, in particu- lar fluorine or chlorine.

Examples of other meanings are : The term"C1-C, 0-alkyl"as used herein and the alkyl moieties of alkylamino and dial- kylamino refer to a saturated straight-chain or branched hydrocarbon group having 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms, especially 1 to 4 carbon groups, for example methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1, 1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-

dimethylpropyl, 1-ethylpropyl, hexyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 1- methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1,2- dimethylbutyl, 1, 3-dimethylbutyl, 2, 2-dimethylbutyl, 2, 3-dimethylbutyl, 3, 3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1, 2-trimethylpropyl, 1,2, 2-trimethylpropyl, 1-ethyl-1- methylpropyl, 1-ethyl-2-methylpropyl, heptyl, octyl, 2-ethylhexyl, nonyl and decyl and their isomers. C1-C4-alkyl means for example methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl or 1, 1-dimethylethyl.

The term"Ct-C6-alkylene chain which may comprise one heteroatom selected from the group consisting of oxygen and sulfuras used herein refers, for example, to methanediyl, ethane-1, 1-diyl, ethane-1, 2-diyl, propane-1, 1-diyl, propane-1, 2-diyl, propane-1, 3-diyl, propane-2, 2-diyl, butane-1, 1-diyl, butane-1, 2-diyl, butane-1, 3-diyl, butane-1, 4-diyl, 2-methylpropane-1, 3-diyl, 2-methylpropane-1, 2-diyl, 2-methylpropane- 1, 1-diyl, 1-methylpropane-1, 2-diyl, 1-methylpropane-2, 2-diyl, 1-methylpropane-1, 1-diyl, pentane-1, 1-diyl, pentane-1, 2-diyl, pentane-1, 3-diyl, pentane-1, 5-diyl, pentane-2, 3-diyl, pentane-2, 2-diyl, 1-methylbutane-1, 1-diyl, 1-methylbutane-1, 2-diyl, 1-methylbutane- 1, 3-diyl, 1-methylbutane-1, 4-diyl, 2-methylbutane-1, 1-diyl, 2-methylbutane-1, 2-diyl, 2- methylbutane-1, 3-diyl, 2-methylbutane-1, 4-diyl, 2, 2-dimethylpropane-1, 1-diyl, 2,2- dimethylpropane-1, 3-diyl, 1, 1-dimethylpropane-1, 3-diyl, 1, 1-dimethylpropane-1, 2-diyl, 2, 3-dimethylpropane-1, 3-diyl, 2, 3-dimethylpropane-1, 2-diyl, 1, 3-dimethylpropane-1, 3- diyl, hexane-1, 1-diyl, hexane-1, 2-diyl, hexane-1, 3-diyl, hexane-1, 4-diyl, hexane-1, 5- diyl, hexane-1, 6-diyl, hexane-2, 5-diyl, 2-methylpentane-1, 1-diyl, 1-methylpentane-1, 2- diyl, 1-methylpentane-1, 3-diyl, 1-methylpentane-1, 4-diyl, 1-methylpentane-1, 5-diyl, 2- methylpentane-1, 1-diyl, 2-methylpentane-1, 2-diyl, 2-methylpentane-1, 3-diyl, 2- methylpentane-1, 4-diyl, 2-methylpentane-1, 5-diyl, 3-methylpentane-1, 1-diyl, 3- methylpentane-1, 2-diyl, 3-methylpentane-1, 3-diyl, 3-methylpentane-1, 4-diyl, 3- methylpentane-1, 5-diyl, 1, 1-dimethylbutane-1, 2-diyl, 1, 1-dimethylbutane-1, 3-diyl, 1,1- dimethylbutane-1, 4-diyl, 1, 2-dimethylbutane-1, 1-diyl, 1, 2-dimethylbutane-1, 2-diyl, 1,2- dimethylbutane-1, 3-diyl, 1, 2-dimethylbutane-1, 4-diyl, 1, 3-dimethylbutane-1, 1-diyl, 1,3- dimethylbutane-1, 2-diyl, 1, 3-dimethylbutane-1, 3-diyl, 1, 3-dimethylbutane-1, 4-diyl, 1- ethylbutane-1, 1-diyl, 1-ethylbutane-1, 2-diyl, 1-ethylbutane-1, 3-diyl, 1-ethylbutane-1, 4- diyl, 2-ethylbutane-1, 1-diyl, 2-ethylbutane-1, 2-diyl, 2-ethylbutane-1, 3-diyl, 2- ethylbutane-1, 4-diyl, 2-ethylbutane-2, 3-diyl, 2, 2-dimethylbutane-1, 1-diyl, 2,2- dimethylbutane-1, 3-diyl, 2, 2-dimethylbutane-1, 4-diyl, 1-isopropylpropane-1, 1-diyl, 1- isopropylpropane-1, 2-diyl, 1-isopropylpropane-1, 3-diyl, 2-isopropylpropane-1, 1-diyl, 2- isopropylpropane-1, 2-diyl, 2-isopropylpropane-1, 3-diyl, 1,2, 3-trimethylpropane-1, 1-diyl, 1,2, 3-trimethylpropane-1, 2-diyl or 1,2, 3-trimethylpropane-1, 3-diyl, preferably ethane- 1, 1-diyl or propane-1, 1-diyl.

When the Ci-C6-alkylene group comprises a heteroatom, the heteroatom can be ar- ranged in the alkylen chain at any position or at the end of the chain so that it con- nects the alkylen chain to the radical R4a. Preferably, the heteroatom is not arranged at the end of the alkylen chain. The heteroatom is preferably oxygen.

The term"C-Cio-haloalkyl"as used herein refers to a straight-chain or branched satu- rated alkyl group having 1 to 10 carbon atoms (as mentioned above), where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as men- tioned above, for example Ci-C4-haloalkyl, such as chloromethyl, bromomethyl, di- chloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chloro- fluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1- fluoroethyl, 2-fluoroethyl, 2, 2-difluoroethyl, 2,2, 2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2- chloro-2, 2-difluoroethyl, 2, 2-dichloro-2-fluoroethyl, 2,2, 2-trichloroethyl, pentafluoroethyl and the like.

The term"C1-C2-fluoroalkyl"as used herein refers to a C1-C2-alkyl which carries 1,2, 3,4 or 5 fluorine atoms, for example difluoromethyl, trifluoromethyl, 1-fluoroethyl, 2- fluoroethyl, 2, 2-difluoroethyl, 2,2, 2-trifluoroethyl, 1,1, 2, 2-tetrafluoroethyl or pentafluoro- ethyl.

The term,"C1-C1o-alkoxy"as used herein refers to a straight-chain or branched satu- rated alkyl group having 1 to 10 carbon atoms (as mentioned above) which is attached via an oxygen atom. Examples include Ci-C6-alkoxy such as methoxy, ethoxy, OCH2- C2H5, OCH (CH3) 2, n-butoxy, OCH (CH3)-C2H5, OCH2-CH (CH3) 2, OC (CH3) 3, n-pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1, 1-dimethylpropoxy, 1, 2-dimethylpropoxy, 2, 2-dimethyl-propoxy, 1-ethylpropoxy, n-hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1, 1-dimethylbutoxy, 1, 2-dimethylbutoxy, 1, 3-dimethylbutoxy, 2, 2-dimethylbutoxy, 2, 3-dimethylbutoxy, 3, 3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1, 2-trimethylpropoxy, 1,2, 2-trimethylpropoxy, 1-ethyl-1-methylpropoxy, 1-ethyl-2- methylpropoxy and the like.

The term"C1-C10-haloalkoxy"as used herein refers to a C1-C10-alkoxy group as men- tioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i. e. , for example, C1-C6-haloalkoxy such as chloromethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluorometh- oxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2, 2-difluoroethoxy, 2,2, 2-trifluoroethoxy, 2-chloro-2- fluoroethoxy, 2-chloro-2, 2-difluoroethoxy, 2, 2-dichloro-2-fluoroethoxy, 2,2, 2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy, 3-fluoropropoxy, 2, 2-difluoropropoxy, 2, 3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2, 3-dichloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 3,3, 3-trifluoropropoxy, 3,3, 3-trichloropropoxy, 2,2, 3,3, 3-pentafluoropropoxy, heptafluoropropoxy, <BR> <BR> 1- (fluoromethyl)-2-fluoroethoxy, 1- (chloromethyl)-2-chloroethoxy, 1- (bromomethyl)-2- bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy, nonafluorobutoxy, 5-fluoro-1-pentoxy, 5-chloro-1-pentoxy, 5-bromo-1-pentoxy, 5-iodo-1-pentoxy, 5,5, 5-trichloro-1-pentoxy, undecafluoropentoxy, 6-fluoro-1-hexoxy, 6-chloro-1-hexoxy, 6-bromo-1-hexoxy, 6-iodo-1-hexoxy, 6,6, 6-trichloro-1-hexoxy or dodecafluorohexoxy, in

particular chloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy or 2,2, 2-trifluoroethoxy.

The term"C1-C6-alkoxy-C1-C6-alkyl"as used herein refers to Cl-C6-alkyl which is sub- stituted by C1-C6-alkoxy as mentioned above, i. e. , for example, CH2-OCH3, CH2- OC2H5, n-propoxymethyl, CH2-OCH (CH3) 2, n-butoxymethyl, (1-methylpropoxy) methyl, (2-methylpropoxy) methyl, CH2-OC (CH3) 3, 2- (methoxy) ethyl, 2- (ethoxy) ethyl, 2- (n- propoxy) ethyl, 2- (1-methylethoxy) ethyl, 2- (n-butoxy) ethyl, 2- (1-methylpropoxy) ethyl, 2- (2-methylpropoxy) ethyl, 2- (1, 1-dimethylethoxy) ethyl, 2- (methoxy) propyl, 2- (ethoxy) propyl, 2-(n-propoxy)propyl, 2-(1-methylethoxy)propyl, 2-(n-butoxy)propyl, 2-(1- methylpropoxy) propyl, 2- (2-methylpropoxy) propyl, 2- (1, 1-dimethylethoxy) propyl, 3- (methoxy) propyl, 3- (ethoxy) propyl, 3- (n-propoxy) propyl, 3- (1-methylethoxy) propyl, 3- (n- butoxy) propyl, 3- (1-methylpropoxy) propyl, 3- (2-methylpropoxy) propyl, 3- (1, 1- dimethylethoxy) propyl, 2- (methoxy) butyl, 2- (ethoxy) butyl, 2- (n-propoxy) butyl, 2- (1- methylethoxy) butyl, 2- (n-butoxy) butyl, 2- (1-methylpropoxy) butyl, 2- (2- methylpropoxy) butyl, 2- (1, 1-dimethylethoxy) butyl, 3- (methoxy) butyl, 3- (ethoxy) butyl, 3- (n-propoxy) butyl, 3-(1-methylethoxy)butyl, 3-(n-butoxy)butyl, 3-(1-methylpropoxy)butyl, 3- (2-methylpropoxy) butyl, 3- (1, 1-dimethylethoxy) butyl, 4- (methoxy) butyl, 4- (ethoxy) butyl, 4- (n-propoxy) butyl, 4- (1-methylethoxy) butyl, 4- (n-butoxy) butyl, 4- (1- methylpropoxy) butyl, 4- (2-methylpropoxy) butyl, 4- (1, 1-dimethylethoxy) butyl and the like.

The term"C1-C6-alkoxy-C1-C6-alkoxy"as used herein refers to Ct-C6-alkoxy which is substituted by Ci-C6-alkoxy as mentioned above, i. e. , for example, OCH2-OCH3, OCH2-OC2H5, n-propoxymethoxy, OCH2-OCH (CH3) 2, n-butoxymethoxy, (1- methylpropoxy) methoxy, (2-methylpropoxy) methoxy, OCH2-OC (CH3) 3, 2- (methoxy) ethoxy, 2- (ethoxy) ethoxy, 2- (n-propoxy) ethoxy, 2-(1-methylethoxy) ethoxy, 2- (n-butoxy) ethoxy, 2-(1-methylpropoxy) ethoxy, 2- (2-methylpropoxy) ethoxy, 2- (1, 1- dimethylethoxy) ethoxy, 2- (methoxy) propoxy, 2- (ethoxy) propoxy, 2- (n-propoxy) propoxy, 2- (1-methylethoxy) propoxy, 2- (n-butoxy) propoxy, 2- (1-methylpropoxy) propoxy, 2- (2- methylpropoxy) propoxy, 2- (1, 1-dimethylethoxy) propoxy, 3- (methoxy) propoxy, 3- (ethoxy) propoxy, 3- (n-propoxy) propoxy, 3-(1-methylethoxy) propv, 3- (n-butoxy) propoxy, 3- (1-methylpropoxy) propoxy, 3- (2-methylpropoxy) propoxy, 3- (1, 1- dimethylethoxy) propoxy, 2- (methoxy) butoxy, 2- (ethoxy) butoxy, 2- (n-propoxy) butoxy, 2- (1-methylethoxy) butoxy, 2- (n-butoxy) butoxy, 2- (1-methylpropoxy) butoxy, 2- (2- methylpropoxy) butoxy, 2- (1, 1-dimethylethoxy) butoxy, 3- (methoxy) butoxy, 3- (ethoxy) butoxy, 3- (n-propoxy) butoxy, 3-(1-methylethoxy) butoxy, 3- (n-butoxy) butoxy, 3- (1-methylpropoxy) butoxy, 3-(2-methylpropoxy) butoxy, 3- (1, 1-dimethylethoxy) butoxy, 4- (methoxy) butoxy, 4- (ethoxy) butoxy, 4- (n-propoxy) butoxy, 4-(1-methylethoxy) butoxy, 4- (n-butoxy) butoxy, 4-(1-methylpropoxy) butoxy, 4- (2-methylpropoxy) butoxy, 4- (1, 1- dimethylethoxy) butoxy and the like.

The term"Ci-C4-alkoxy-Ci-C4-alkoxy-C1-C4-alkoxy"as used herein refers to C1-C4- alkoxy which is substituted by Ci-C4-aikoxy-Ci-C4-alkoxy as mentioned above, i. e. , for example, 2-(2-methoxyethyloxy)ethyloxy, 2-(2-ethoxyethyloxy)ethyloxy ; The term"C1-C1o-alkylcarbonyl"as used herein refers to a straight-chain or branched saturated alkyl group having 1 to 10 carbon atoms (as mentioned above) bonded via the carbon atom of the carbonyl group at any bond in the alkyl group. Examples include Ct-C6-alkylcarbonyl such CO-CH3, CO-C2H5, n-propylcarbonyl, 1-methylethylcarbonyl, n-butylcarbonyl, 1-methylpropylcarbonyl, 2-methylpropylcarbonyl, 1, 1- <BR> <BR> dimethylethylcarbonyl, n-pentylcarbonyl, 1-methylbutylcarbonyl, 2-methylbutylcarbonyl, 3-methylbutylcarbonyl, 1, 1-dimethylpropylcarbonyl, 1, 2-dimethylpropylcarbonyl, 2,2- dimethylpropylcarbonyl, 1-ethylpropylcarbonyl, n-hexylcarbonyl, 1- methylpentylcarbonyl, 2-methylpentylcarbonyl, 3-methylpentylcarbonyl, 4- methylpentylcarbonyl, 1, 1-dimethylbutylcarbonyl, 1, 2-dimethylbutylcarbonyl, 1,3- dimethylbutylcarbonyl, 2, 2-dimethylbutylcarbonyl, 2, 3-dimethylbutylcarbonyl, 3,3- dimethylbutylcarbonyl, 1-ethylbutylcarbonyl, 2-ethylbutylcarbonyl, 1,1, 2- trimethylpropylcarbonyl, 1,2, 2-trimethylpropylcarbonyl, 1-ethyl-1-methylpropylcarbonyl or 1-ethyl-2-methylpropylcarbonyl and the like.

The term"C1-C10-alkoxycarbonyl"as used herein refers to a straight-chain or branched alkoxy group (as mentioned above) having 1 to 10 carbon atoms attached via the carbon atom of the carbonyl group. Examples include (C1-C6-alkoxy) carbonyl, for example CO-OCH3, CO-OC2H5, COO-CH2-C2H5, CO-OCH (CH3) 2, n-butoxycarbonyl, CO-OCH (CH3)-C2H5, CO-OCH2-CH (CH3) 2, CO-OC (CH3) 3, n-pentoxycarbonyl, 1- methylbutoxycarbonyl, 2-0methylbutoxycarbonyl, 3-methylbutoxycarbonyl, 2,2- dimethylpropoxycarbonyl, 1-ethylpropoxycarbonyl, n-hexoxycarbonyl, 1,1- dimethylpropoxycarbonyl, 1, 2-dimethylpropoxycarbonyl, 1-methylpentoxycarbonyl, 2- methylpentoxycarbonyl, 3-methylpentoxycarbonyl, 4-methylpentoxycarbonyl, 1,1- dimethylbutoxycarbonyl, 1, 2-dimethylbutoxycarbonyl, 1, 3-dimethylbutoxycarbonyl, 2,2- dimethylbutoxycarbonyl, 2, 3-dimethylbutoxycarbonyl, 3, 3-dimethylbutoxycarbonyl, 1- ethylbutoxycarbonyl, 2-ethylbutoxycarbonyl, 1,1, 2-trimethylpropoxycarbonyl, 1,2, 2- trimethylpropoxycarbonyl, 1-ethyl-1-methylpropoxycarbonyl or 1-ethyl-2- methylpropoxycarbonyl The term "C1-C10-alkylthio (C1-C10-alkylsulfanyl : C1-C10-alkyl-S-)"as used herein refers to a straight-chain or branched saturated alkyl group having 1 to 10 carbon atoms (as mentioned above) which is attached via a sulfur atom, for example Ci-C4-alkylthio such as methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2- methylpropylthio or 1, 1-dimethylethylthio.

The term"Ci-C1o-alkylsulfinyl" (Ci-C1o-alkyl-S (=O)-), as used herein refers to a straight-chain or branched saturated hydrocarbon group (as mentioned above) having 1 to 10 carbon atoms bonded through the sulfur atom of the sulfinyl group at any bond in the alkyl group. Examples include C1-C6-alkylsulfinyl : SO-CH3, SO-C2H5, n-

propyisulfinyl, 1-methylethylsulfinyl, n-butylsulfinyl, 1-methylpropylsulfinyl, 2- methylpropylsulfinyl, 1, 1-dimethylethylsulfinyl, n-pentylsulfinyl, 1-methylbutylsulfinyl, 2- methylbutylsulfinyl, 3-methylbutylsulfinyl, 1, 1-dimethylpropylsulfinyl, 1,2- dimethylpropylsulfinyl, 2, 2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, n-hexylsulfinyl, 1-methylpentylsulfinyl, 2-methylpentylsulfinyl, 3-methylpentylsulfinyl, 4- methylpentylsulfinyl, 1, 1-dimethylbutylsulfinyl, 1, 2-dimethylbutylsulfinyl, 1,3- dimethylbutylsulfinyl, 2, 2-dimethylbutylsulfinyl, 2, 3-dimethylbutylsulfinyl, 3,3- dimethylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl, 1,1, 2- trimethylpropylsulfinyl, 1,2, 2-trimethylpropylsulfinyl, 1-ethyl-1-methylpropylsulfinyl or 1- ethyl-2-methylpropylsulfinyl.

The term"Ci-Cio-alkylsulfonyl" (C1-Cio-alkyl-S (=O) 2-) as used herein refers to a straight-chain or branched saturated alkyl group having 1 to 10 carbon atoms (as men- tioned above) which is bonded via the sulfur atom of the sulfonyl group at any bond in the alkyl group. Examples include Ci-C6-alkylsulfonyl such as SO2-CH3, SO2-C2H5, n- propylsulfonyl, S02-CH (CH3) 2, n-butylsulfonyl, 1-methylpropylsulfonyl, 2- methylpropylsulfonyl, SO2-C (CH3) 3, n-pentylsulfonyl, 1-methylbutylsulfonyl, 2- methylbutylsulfonyl, 3-methylbutylsulfonyl, 1, 1-dimethylpropylsulfonyl, 1,2- dimethylpropylsulfonyl, 2, 2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, n- hexylsulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4- methylpentylsulfonyl, 1, 1-dimethylbutylsulfonyl, 1, 2-dimethylbutylsulfonyl, 1,3- dimethylbutylsulfonyl, 2, 2-dimethylbutylsulfonyl, 2, 3-dimethylbutylsulfonyl, 3,3- dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1,1, 2- trimethylpropylsulfonyl, 1,2, 2-trimethylpropylsulfonyl, 1-ethyl-1-methylpropylsulfonyl or 1-ethyl-2-methylpropylsulfonyl and the like.

The term"C2-C10-alkenyl"as used herein refers to a straight-chain or branched unsatu- rated hydrocarbon group having 2 to 10 carbon atoms and a double bond in any posi- tion, such as ethenyl, 1-propenyl, 2-propenyl, 1-methyl-ethenyl, 1-butenyl, 2-butenyl, 3- butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2- propenyl ; 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl- 1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2- butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1, 1-dimethyl-2- propenyl, 1, 2-dimethyl-1-propenyl, 1, 2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl- 2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1- pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2- pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3- pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4- pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1, 1-dimethyl- 2-butenyl, 1, 1-dimethyl-3-butenyl, 1, 2-dimethyl-l-butenyl, 1, 2-dimethyl-2-butenyl, 1,2- dimethyl-3-butenyl, 1, 3-dimethyl-1-butenyl, 1, 3-dimethyl-2-butenyl, 1, 3-dimethyl-3- butenyl, 2, 2-dimethyl-3-butenyl, 2, 3-dimethyl-1-butenyl, 2, 3-dimethyl-2-butenyl, 2,3- dimethyl-3-butenyl, 3, 3-dimethyl-1-butenyl, 3, 3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1- ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-

butenyl, 1,1, 2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1- propenyl and 1-ethyl-2-methyl-2-propenyl ; The term"C2-Clo-alkynyl"as used herein refers to a straight-chain or branched unsatu- rated hydrocarbon group having 2 to 10 carbon atoms and containing at least one triple bond, such as ethynyl, prop-1-yn-1-yl, prop-2-yn-1-yl, n-but-1-yn-1-yl, n-but-1-yn-3-yl, n-but-1-yn-4-yl, n-but-2-yn-1-yl, n-pent-1-yn-1-yl, n-pent-1-yn-3-yl, n-pent-1-yn-4-yl, n- pent-1-yn-5-yl, n-pent-2-yn-1-yl, n-pent-2-yn-4-yl, n-pent-2-yn-5-yl, 3-methylbut-1-yn-3- yl, 3-methylbut-1-yn-4-yl, n-hex-1-yn-1-yl, n-hex-1-yn-3-yl, n-hex-1-yn-4-yl, n-hex-1-yn- 5-yl, n-hex-1-yn-6-yl, n-hex-2-yn-1-yl, n-hex-2-yn-4-yl, n-hex-2-yn-5-yl, n-hex-2-yn-6-yl, n-hex-3-yn-1-yl, n-hex-3-yn-2-yl, 3-methylpent-1-yn-1-yl, 3-methylpent-1-yn-3-yl, 3- <BR> <BR> methylpent-1-yn-4-yl, 3-methylpent-1-yn-5-yl, 4-methylpent-1-yn-1-yl, 4-methylpent-2- yn-4-yl or 4-methylpent-2-yn-5-yl and the like.

The term"C3-C10-cycloalkyl"as used herein refers to a monocyclic hydrocarbon radi- cal having 3 to 10 carbon atoms, in particular 3 to 8 carbon atoms, e. g. cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl or cyclodecyl, The term"C3-C8-cycloalkyl-C1-C4-alkyl"as used herein refers to a Ci-C4-alkyl which carries a C3-C8-cycloalkyl radical as defined above, for example cyclopropylmethyl, 1- cyclopropylethyl, 2-cyclopropylethyl, 1-cyclopropylprop-1-yl, 2-cyclopropylprop-1-yl, 3- cyclopropylprop-1-yl, 1-cyclopropylbut-1-yl, 2-cyclopropylbut-1-yl, 3-cyclopropylbut-1-yl, 4-cyclopropylbut-1-yl, 1-cyclopropylbut-2-yl, 2-cyclopropylbut-2-yl, 3-cyclopropylbut-2- yl, 3-cyclopropylbut-2-yl, 4-cyclopropylbut-2-yl, 1-(cyclopropylmethyl)-eth-1-yl, 1- <BR> <BR> (cyclopropylmethyl)-1- (methyl)-eth-1-yl, 1- (cyclopropylmethyl)-prop-1-yl, cyclobutyl-<BR> <BR> <BR> <BR> <BR> <BR> methyl, 1-cyclobutylethyl, 2-cyclobutylethyl, 1-cyclobutylprop-1-yl, 2-cyclobutylprop-1-<BR> <BR> <BR> <BR> <BR> yl, 3-cyclobutylprop-1-yl, 1-cyclobutylbut-1-yl, 2-cyclobutylbut-1-yl, 3-cyclobutylbut-1-yl, 4-cyclobutylbut-1-yl, 1-cyclobutylbut-2-yl, 2-cyclobutylbut-2-yl, 3-cyclobutylbut-2-yl, 3- cyclobutylbut-2-yl, 4-cyclobutylbut-2-yl, 1- (cyclobutylmethyl) eth-1-yl, 1- <BR> <BR> (cyclobutylmethyl)-1- (methyl)-eth-1-yl, 1- (cyclobutylmethyl) prop-1-yl, cyclopentylmethyl, 1-cyclopentylethyl, 2-cyclopentylethyl, 1-cyclopentylprop-1-yl, 2-cyclopentylprop-1-yl, 3- cyclopentylprop-1-yl, 1-cyclopentylbut-1-yl, 2-cyclopentylbut-1-yl, 3-cyclopentylbut-1-yl, 4-cyclopentylbut-1-yl, 1-cyclopentylbut-2-yl, 2-cyclopentylbut-2-yl, 3-cyclopentylbut-2-yl, 3-cyclopentylbut-2-yl, 4-cyclopentylbut-2-yl, 1-(cyclopentylmethyl)-eth-1-yl, 1- (cyclopentyl methyl)-1-(methyl)-eth-1-yl, 1-(cyclopentylmethyl)-prop-1-yl, cyclohexyl- methyl, 1-cyclohexylethyl, 2-cyclohexylethyl, 1-cyclohexylprop-1-yl, 2-cyclohexylprop-1- <BR> <BR> yl, 3-cyclohexylprop-1-yl, 1-cyclohexylbut-1-yl, 2-cyclohexylbut-1-yl, 3-cyclohexylbut-1- yl, 4-cyclohexylbut-1-yl, 1-cyclohexylbut-2-yl, 2-cyclohexylbut-2-yl, 3-cyclohexylbut-2-yl, 3-cyclohexylbut-2-yl, 4-cyclohexylbut-2-yl, 1- (cyclohexylmethyl)-eth-1-yl, 1- (cyclohexylmethyl)-1-(methyl)-eth-1-yl, 1-(cyclohexylmethyl)-prop-1-yl, cycloheptyl- methyl, 1-cycloheptylethyl, 2-cycloheptylethyl, 1-cycloheptylprop-1-yl, 2- <BR> <BR> cycloheptylprop-1-yl, 3-cycloheptylprop-1-yl, 1-cycloheptylbut-1-yi, 2-cycloheptylbut-1-<BR> <BR> <BR> <BR> <BR> <BR> yl, 3-cycloheptylbut-1-yl, 4-cycloheptylbut-1-yl, 1-cycloheptylbut-2-yl, 2-cycloheptylbut- 2-yl, 3-cycloheptylbut-2-yl, 3-cycloheptylbut-2-yl, 4-cycloheptylbut-2-yl, 1-

(cycloheptylmethyl)-eth-1-yl, 1-(cycloheptylmethyl)-1-(methyl)-eth-1-yl, 1- (cycloheptylmethyl)-prop-1-yl, cyclooctylmethyl, 1-cyclooctylethyl, 2-cyclooctylethyl, 1- cyclooctylprop-1-yl, 2-cyclooctylprop-1-yl, 3-cyclooctylprop-1-yl, 1-cyclooctylbut-1-yl, 2- cyclooctylbut-1-yl, 3-cyclooctylbut-1-yl, 4-cyclooctylbut-1-yl, 1-cyclooctylbut-2-yl, 2- cyclooctylbut-2-yl, 3-cyclooctylbut-2-yl, 3-cyclooctylbut-2-yl, 4-cyclooctylbut-2-yl, 1- (cyclooctylmethyl)-eth-1-yl, 1-(cyclooctylmethyl)-1-(methyl)-eth-1-yl or 1- (cyclooctylmethyl)-prop-1-yl.

The term"phenyl-C1-C4-alkyl"as used herein refers to C1-C4-alkyl which is substituted by phenyl, which may for its part be unsubstituted or carries one, two or three substitu- ents, such as benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylprop-1-yl, 2-phenylprop-1- yl, 3-phenylprop-1-yl, 1-phenylbut-1-yi, 2-phenylbut-1-yl, 3-phenylbut-1-yl, 4-phenylbut- 1-yl, 1-phenylbut-2-yl, 2-phenylbut-2-yl, 3-phenylbut-2-yl, 4-phenylbut-2-yl, 1- (benzyl) eth-1-yl, 1-(benzyl)-1-(methyl) eth-1-yl or 1- (benzyl)-prop-1-yl, preferably ben- zyl, 1-phenylethyl or 2-phenylethyl and especially (R)-1-phenylethyl and (S)-1- phenylethyl.

The term"heterocyclyl"as used herein refers to a 3-to 7-membered heterocyclic radical which has 3,4, 5,6 or 7 ring members, where 1,2 or 3 of these ring members are heteroatoms selected, independently from each other, from the group consisting of oxygen, nitrogen, sulfur and a group NR wherein R5 has the meanings as defined above. The heterocycle may be a carbon-bonded heterocycle or may be bonded via a heteroatom. The heterocycle may be aromatic (heteroaryl) or partially or fully saturated.

Moreover, the heterocyclyl radical may be fused to a 5-to 7-membered saturated, un- saturated or aromatic carbocyclic ring or to a 5-to 7-membered heterocyclic ring which may carry for their part one, two, three, four, five or six substituents which are selected, independently from another from the group consisting of halogen such as fluorine, chlo- rine, bromine and C1-C4-alkyl such as methyl.

Examples for monocyclic heteroaromatic rings include triazinyl, pyrazinyl, pyrimidyl, pyridazinyl, pyridyl, thienyl, furyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, thia- zolyl, oxazolyl, thiadiazolyl, oxadiazolyl, isothiazolyl or isoxazolyl.

Examples for non-aromatic rings include pyrrolidinyl, pyrazolinyl, imidazolinyl, pyr- rolinyl, pyrazolinyl, imidazolinyl, tetrahydrofuranyl, dihydrofuranyl, 1, 3-dioxolanyl, di- oxolenyl, thiolanyl, dihydrothiophenyl, oxazolidinyl, isoxazolidinyl, oxazolinyl, isoxa- zolinyl, thiazolinyl, isothiazolinyl, thiazolidinyl, isothiazolidinyl, oxathiolanyl, piperidinyl, piperazinyl, pyranyl, dihydropyranyl, tetrahydropyranyl, dioxanyl, thiopyranyl, dihy- drothiopyranyl, tetrahydrothiopyranyl, morpholinyl, thiazinyl and the like.

The term"fused to a 5-to 7-membered saturated, unsaturated or aromatic carbo- cyclic ring or to a 5-to 7-membered heterocyclic ring"as used herein refers to a cyclic radical which carries a fused saturatedC5-C7-carbocycle as defined above, a

mono-or diunsaturated C5-C7-carbocycle or phenyl or to a 5-7-membered heterocyclic ring as defined above.

Examples for C3-Cio-cycloalkyl fused with a 5-to 7-membered saturated, unsaturated or aromatic carbocyclic ring are indan-1-yl, indan-2-yl, 1,2, 3, 4-tetrahydronaphthalen-1- yl, 1,2, 3, 4-tetrahydronaphthalen-2-yl, decalin-1-yl, decalin-2-yl or hydrindanyl and the like.

Examples for phenyl fused with a 5-to 7-membered saturated, unsaturated or aromatic carbocyclic ring or to a 5-to 7-membered heterocyclic ring are indan-5-yl, indan-6-yl, dihydronaphthalen-5-yl, dihydronaphthalen-6-yl, 1,2, 3, 4-tetrahydronaphthalen-5-yl, 1,2, 3, 4-tetrahydronaphthalen-6-yl, quinolinyl, isoquinolinyl, indolyl, indolizinyl, isoindo- lyl, indazolyl, benzofuryl, benzthienyl, benzthiazolyi, benzoxazolyl, 1, 3-benzodioxolyl, 1, 4-benzodioxanyl, benzimidazolyl, dihydroindolyi, dihydroindolizinyl, dihydroisoindolyl, dihydrochinolinyl, dihydroisochinolinyl, chromenyl, chromanyl and the like.

Examples for 3-to 7-membered heterocyclyl carrying a fused-on 5-to 7-membered saturated, unsaturated or aromatic carbocyclic ring or a 5-to 7-membered heterocyclic ring are quinolinyl, isoquinolinyl, indolyl, indolizinyl, isoindolyl, indazolyl, benzofuryl, benzthienyl, benzthiazolyl, benzoxazolyl, 1, 3-benzodioxolyl, 1, 4-benzodioxanyl, ben- zimidazolyl, dihydroindolyl, dihydroindolizinyl, dihydroisoindolyl, dihydrochinolinyl, dihy- droisochinolinyl, chromenyl, chromanyl and the like.

As regards the pesticidal activity of the 6-halogeno- [1, 2, 4]-triazolo [1,5-a]-pyrimidine of the general formula 1, preference is given to those compounds 1, in which the radical R4 is attached to the nitrogen atom of the amino group via a secondary or tertiary carbon atom. Thus, compounds I are preferred, wherein R4 is phenyl, naphthyl, C3-C10- cycloalkyl, a 3-to 7-membered heterocyclyl or a radical-A-R4a, wherein A C2-C6- alkylen which is attached to the nitrogen via a secondary or tertiary carbon atom of the C2-C6-alkylene chain. The C2-C6-alkylene chain may comprise a heteroatom se- lected from the group consisting of oxygen and sulfur. The compounds comprise the pure R-and S-enantiomers as well as the mixtures of the enantiomers such as the ra- cemic mixtures. Particularly preferred among these are the pure enantiomers.

As regards the pesticidal activity of the 6-halogeno- [1, 2, 4]-triazolo [1, 5-a]-pyrimidine of the general formula 1, preference is also given to the following meaning of the radicals, in each case on their own or in combination: X is chlorine; R'is hydrogen, Ci-C4-alkyl, preferably methyl, Ci-C4-haloalkyl, preferably trifluoro- methyl, C1-C4-alkoxy, preferably methoxy, C1-C4-alkylthio, preferably methylthio, C1-C4-alkylsulfinyl, preferably methylsulfinyl or C1-C4-alkylsulfonyl, preferably me- thylsulfonyl, most preferred hydrogen; however R'may also be OH, CN, Phenoxy, Benzyloxy, C-C4-alkoxy-C2-C4-alkoxy, Ct-C4-alkoxy-C2-C4-alkoxy-C2- C4-alkoxy, (Ct-C4-alkoxycarbonyl) C2-C4-alkylthio, such as 2-

(methoxycarbonyl) ethylthio, 2- (ethoxycarbonyl) ethylthio, SCH2-CO-OCH3 or SCH2-CO-OCH2CH3, (hydroxycarbonyl) C2-C4-alkylthio, such as S-CH2-COOH, S-CH2CH2-COOH, (C1-C4-alkoxy)C2-C4-alkylthio such as SCH2-CH2-OCH3 or SCH2-CH2-OCH2CH3 ; R2 is Ci-C4-alkyl, preferably C1-C2-alkyl, or C1-C4-haloalkyl, preferably C1-C2- fluoroalkyl ; most preferred methyl, ethyl, 2-fluoroethyl or 1-fluoroethyl ; R3 is hydrogen or Ci-C4-alkoxy-Ci-C4-alkyl, most preferred hydrogen; R4 is phenyl, phenyl-C1-C4-alkyl or C3-C8-cycloalkyl, wherein each phenyl and C3-C8- cycloalkyl group may be unsubstituted or may carry one or two substituents which are selected, independently from one another, from the group consisting of halogen, C1-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-haloalkoxy, Ci-C4-alkoxy, C3-C8- cycloalkyl-Ci-C4-alkyl, phenyl and phenyloxy, wherein the three last-mentioned substituents for their part may be unsubstituted or may carry one or two substitu- ents which are selected, independently from each other, from the group consist- ing of C1-C4-alkyl, C1-C4-alkoxy and halogen.

A preferred embodiment of the invention are compounds of the general formula 1, wherein R4 is cyclohexyl, benzyl, 1-phenylethyl or 2-phenylethyl, wherein the cyclo- hexyl group and the phenyl group in the last three mentioned radicals may be unsubsti- tuted or may carry one or two substituents which are selected, independently from each other, from the group consisting of halogen, C1-C4-alkyl, Ci-C4-haloalkoxy, Ci-C4- haloalkyl, C1-C4-alkoxy, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, phenyl and phenyloxy, wherein the two last mentioned substituents for their part may be unsubsti- tuted or may carry one or two substituents which are selected independently of each other from the group consisting of Ci-C4-alkyl, C,-C4-alkoxy and halogen.

In an especially preferred embodiment of the present invention, R4 is a cyclohexyl radi- cal which may carry one or two substituents. One substituent is preferably attached to the 4-position of the cyclohexyl radical. Particularly preferred substituents of the radical cyclohexyl mentioned for R4 are, independently of one another, Ci-C4-alkyl, especially methyl, ethyl, isopropyl, sec-butyl and tert-butyl or cyclohexyl-Ci-C4-alkyl. Amongst the compounds I those are especially preferred, wherein the cyclohexyl radical carries a substituent in the 4-position, said substituent is most preferably attached cis relative to the nitrogen atom.

In another embodiment of the present invention, particular preference is given to 6- halogeno- [1, 2,4] triazolo [1,5-a] pyrimidines in which R4 is phenyl, benzyl, 1-phenylethyl or 2-phenylethyl which for their part carry one or two of the above defined substituents on the phenyl ring.

The substituents are preferably selected independently of each other from the group consisting fluorine, chlorine, bromine, C1-C4-alkyl especially methyl, ethyl, n-propyl, isopropyl, 2-butyl and tert-butyl; C1-C4-alkoxy, especially methoxy, ethoxy, tert-butoxy, <BR> <BR> C1-C4-haloalkyl, especially trifluoromethyl and C1-C4-haloalkoxy, especially trifluorodi-

fluoromethoxy, trifluoromethoxy, 1,1, 2, 2-tetrafluoroethoxy. In this embodiment, com- pounds are especially preferred, wherein R4 is 1-phenylethyl which carries at least one substituent as defined above, especially one which has been indicated as preferred.

Most preferably said substituent is attached in the 4-position of the phenyl radical. Par- ticularly preferred among these are compounds I in which R4 is the pure enantiomer or a racemic mixture.

In another embodiment of the invention the radical R4 comprises a phenyl group such as in phenyl, benzyl and 1-or-2-phenylethyl, wherein the the phenyl ring carries at least one substituent which is selected from the group consisting of phenyl, cyclohexyl and phenoxy which for their part may be unsubstituted or may carry in the 2-, 3-or 4- position one or two substituents selected from the group consisting of C1-C4-alkyl, es- pecially methyl, ethyl, n-propyl or isopropyl, Ci-C4-alkoxy such as methoxy and halo- gen, especially fluorine, chlorine or bromine. Examples of substituents on the phenyl ring of phenyl, benzyl, 1-phenylethyl, or 2-phenylethyl are: 4-methylphenoxy, 4- ethylphenoxy, 4-isopropylphenoxy, 4-tert-butylphenoxy, 4-fluorophenoxy, 4- chlorophenoxy, 4-bromophenoxy, 2-methylphenoxy, 2-tert-butylphenoxy, 2- ethylphenoxy, 3-ethylphenoxy, 2-bromophenoxy, 2-chlorophenoxy, 3-chlorophenoxy, 3- bromophenoxy, 3, 4-difluorophenoxy, 3-chloro-4-fluorophenoxy, 4-bromo-3- chlorophenoxy, 4-chloro-3-fluorophenoxy, 3, 4-dichlorophenoxy, 3, 4-dimethlyphenoxy, 3-chloro-4-methylphenoxy, 3-methyl-4-chlorophenoxy or 3-methyl-4-bromophenoxy.

Examples of compounds are the 6-chloro- [1, 2,4] triazolo- [1, 5-a] pyrimidines of the for- mula la (s i where X = Cl and R'= R3= H), where R2 and R4 together have the mean- ings given in one row of Table A.

Table A: No. R2 R4 A-1. CH3 4-CH3-cyclohexyl- A-2. CH3 cis-4-CH3-cyclohexyl- A-3. CH3 trans-4-CH3-cyclohexyl- A-4. CH3 4-C2Hs-cyclohexyl- A-5. CH3 cis-4-C2H5-cyclohexyl- A-6. CH3 trans-4-C2H5-cyclohexyl- A-7. CH3 4-n-propyl-cyclohexyl- A-8. CH3 cis-4-n-propyl-cyclohexyl- No. R2 R4 A-9. CH3 trans-4-n-propyl-cyclohexyl- A-10. CH3 4-isopropyl-cyclohexyl- A-11. CH3 cis-4-isopropyl-cyclohexyl- A-12. CH3 trans-4-isopropi-cyclohexyl- A-13. CH3 4-n-butylcyclohexyl- A-14. CH3 cis-4-n-butylcyclohexyl- A-15. CH3 trans-4-n-butylcyclohexyl- A-16. CH3 4-tert-butylcyclohexyl- A-17. CH3 cis-4-tert-butylcyclohexyl- A-18. CH3 trans-4-tert-butylcyclohexyl- A-19. CH3 4-(2-butyl)cyclohexyl- A-20. CH3 (2-butyl) cyclohexyl- A-21. CH3 trans-4- (2-butyl) cyclohexyl- A-22. CH3 (cyclohexyl-C (CH3) 2)-cyclohexyl- A-23. CH3 cis-4-(cyclohexyl-C (CH3) 2)-cyclohexyl- A-24. CH3 trans-4-(cyclohexyl-C(CH3)2)-cyclohexyl- A-25. CH3 C6H5- A-26. CH3 4-F-C6H4- A-27. CH3 4-CI-C6H4- A-28. CH3 4-Br-C6H4- A-29. CH3 4-(C6H5)-C6H4- A-30. CH3 4-phenoxyphenyl A-31. Cl3 benzyl A-32. CH3 4-CH3-C6H4-CH2- A-33. CH3 4-C2H5-C6H4-CH2- A-34. CH3 4-n-C3H7-C6H4-CH2- A-35. CH3 4-isopropyl-C6H4-CH2- A-36. CH3 4-n-C4H9-C6H4-CH2- A-37. CH3 4-isobutyl-C6H4-CH2- A-38. CH3 4-tert-buyl-C6H4CH2- A-39. CH3 4-F3C-C6H4CH2- A-40. CH3 4-methoxy-C6H4CH2- A-41. CH3 4-ethoxy-C6H4CH2- A-42. CH3 4-n-propoxy-C6H4CH2- A-43. CH3 4-isopropoxy-C6H4CH2- A-44. CH3 4-n-butoxy-C6H4CH2- A-45. CH3 4-tert-butoxy-C6H4CH2- A-46. CH3 4-F-C6H4CH2- A-47. CH3 4-Cl-C6H4CH2- A-48. CH3 4-Br-C6H4CH2- A-49. CH3 3,4-F2-C6H3CH2- No. R2 R4 A-50. CH3 3, 4-CI2-C6H3CH2- A-51. CH3 3, 4-Br2-C6H3CH2- A-52. CH3 4-(4-CH3-C6H4-O)-C6H4-CH2- A-53. CH3 4-(4-C2H5-C6H4-O)-C6H4-CH2- A-54. CH3 4-(4-n-C3H7-C6H4-O)-C6H4-CH2- A-55. CH3 4-(4-iso-C3H7-C6H4-O)-C6H4-CH2- A-56. CH3 4-(4-n-C4H9-C6H4-O)-C6H4-CH2- A-57. CH3 4-(4-iso-C4H9-C6H4-O)-C6H4-CH2- A-58. CH3 4-(4-tert-C4H9-C6H4-O)-C6H4-CH2- A-59. CH3 4-(4-H3C-O-C6H4-O)-C6H4-CH2- A-60. CH3 4-(4-H3C-H2C-O-C6H4-O)-C6H4-CH2- A-61. CH3 4-(4-H3C-H2C-H2C-O-C6H4-O)-C6H4-CH2- A-62. CH3 4-(4-H3C-H2C-H2C-H2C-O-C6H4-O)-C6H4-CH2- A-63. CH3 4-4-tert-butoxy-C6H4-O)-C6H4-CH2- A-64. CH3 4-(4-Cl-C6H4-O)-C6H4-CH2- A-65. CH3 4-(4-Br-C6H4-O)-C6H4-CH2- A-66. CH3 4-(3-CH3-C6H4-O)-C6H4-CH2- A-67. CH3 4-(3-C2H5-C6H4-O)-C6H4-CH2- A-68. CH3 4-(3-n-C3H7-C6H4-O)-C6H4-CH2- A-69. CH3 4-(3-iso-C3H7-C6H4-O)-C6H4-CH2- A-70. CH3 4-(3-n-C4H9-C6H4-O)-C6H4-CH2- A-71. CH3 4-(3-iso-C4H9-C6H4-O)-C6H4-CH2- A-72. CH3 4-(3-tert-butyl-C6H4-O)C6H4-CH2- A-73. CH3 4-(3-H3C-O-C6H4-O)-C6H4-CH2- A-74. CH3 4-(3-H3C-H2C-O-C6H4-O)-C6H4-CH2- A-75. CH3 4-(3-H3C-H2C-H2C-O-C6H4-O)-C6H4-CH2- A-76. CH3 4-(3-H3C-H2C-H2C-H2C-O-C6H4-O)-C6H4-CH2- A-77. CH3 4-(3-tert-butoxy-C6H4-O)-C6H4-CH2- A-78. CH3 4-(3-F-C6H4-O)-C6H4-CH2- A-79. CH3 4-(3-Cl-C6H4-O)-C6H4-CH2- A-80. CH3 4-(3-Br-C6H4-O)-C6H4-CH2- A-81. CH3 4-(2-CH3-C6H4-O)-C6H4-CH2- A-82. CH3 4-(2-C2H5-C6H4-O)-C6H4-CH2- A-83. CH3 4-(2-n-C3H7-C6H4-O)-C6H4-CH2- A-84. CH3 4-2-iso-C3H7-C6H4-0)-C6H4-CH2- A-85. CH3 4-(2-n-C4Hg-C6H4-O)-C6H4-CH2- A-86. CH3 (2-iso-C4H9-C6H4-0)-C6H4-CH2- A-87. CH3 4-(2-tert-butyl-C6H4-O)-C6H4-CH2- A-88. CH3 4-(2-H3C-O-C6H4-O)-C6H4-CH2- A-89. CH3 4-(2-H3C-H2C-O-C6H4-O)-C6H4-CH2- A-90. CH3 4-2-H3C-H2C-H2C-O-C6H4-O-C6H4-CH2- No. R2 R4 A-91. CH3 (2-H3C-H2C-H2C-H2C-0-C6H4-0)-C6H4-CH2- A-92. CH3 4-(2-tert-butoxy-C6H4-O)-C6H4-CH2- A-93. CH3 4-(2-F-C6H4-O)-C6H4-CH2- A-94. CH3 4-(2-Cl-C6H4-O)-C6H4-CH2- A-95. CH3 4-(2-Br-C6H4-O)-C6HY4-CH2- A-96. CH3 4-(3,4-F2-C6H3-O)-C6H4-CH2- A-97. CH3 4-(3,4-Cl2-C6H3-O)-C6H4-CH2- A-98. CH3 4-(3,4-(CH3)2-C6H3-O)-C6H4-CH2- A-99. CH3 4-(3-F-4-Cl-C6H3-O)-C6H4-CH2- A-100. CH3 4-(3-Cl-4-F-C6H3-O)-C6H4-CH2- A-101. CH3 4-(3-CH3-4-Cl-C6H3-O)-C6H4-CH2- A-102. CH3 4-(3-Cl-4-CH3-C6H3-O)-C6H4-CH2- A-103. CH3 4-(3-Cl-4-Br-C6H3-O)-C6H4-CH2- A-104. CH3 4-(3-CH3-4-Br-C6H3-O)-C6H4-CH2- A-105. CH3 () phenyl-CH (CH3)- A-106. CH3 (R) phenyl-CH(CH3)- A-107. CH3 (S) phenyl-CH (CH3)- A-108. CH3 (~) 4-F-phenyl-CH(CH3)- A-109. CH3 (R) 4-F-phenyl-CH (CH3)- A-110. CH3 (S) 4-F-phenyl-CH (CH3)- A-111. CH3 (~) 4-Cl-phenyl-CH(CH3)- A-112. CH3 (R) 4-CI-phenyl-CH (CH3)- A-113. CH3 (S) 4-CI-phenyl-CH (CH3)- A-114. CH3 (~) 4-Br-phenyl-CH(CH3)- A-115. CH3 (R) 4-Br-phenyl-CH(CH3)- A-116. CH3 (S) 4-Br-phenyl-CH(CH3)- A-117. CH3 (~) 4-Cl-2-F-phenyl-CH(CH3)- A-118. CH3 (R) 4-Cl-2-F-phenyl-CH(CH3)- A-119. CH3 (S) 4-Cl-2-F-phenyl-CH(CH3)- A-120. CH3 (~) 6-Cl-2-F-phenyl-CH(CH3)- A-121. CH3 (R) 6-CI-2-F-phenyl-CH (CH3)- A-122. CH3 (S) 6-CI-2-F-phenyl-CH (CH3)- A-123. CH3 () 2-F-phenyl-CH (CH3)- A-124. CH3 (R) 2-F-phenyl-CH (CH3)- A-125. CH3 (S) 2-F-phenyl-CH (CH3)- A-126. CH3 (S) 2, 4-F2-phenyl-CH(CH3)- A-127. CH3 () 2, 4-F2-phenyl-CH(CH3)- A-128. CH3 (R) 2, 4-F2-phenyl-CH(CH3)- A-129. CH3 (S 2, 5-F2-phenyl-CH(CH3)- A-130. CH3 () 2, 5-F2-phenyl-CH(CH3)- A-131. CH3 (R) 2, 5-F2-phenyl-CH (CH3)- No. R2 R4 A-132. CH3 (S) 2, 6-F2-phenyl-CH(CH3)- A-133. CH3 () 2, 6-F2-phenyl-CH(CH3)- A-134. CH3 (R 2, 6-F2-phenyl-CH(CH3)- A-135. CH3 () 2-CH3O-phenyl-CH(CH3)- A-136. CH3 (R) 2-CH3O-phenyl-CH(CH3)- A-137. CH3 (S) 2-CH3O-phenyl-CH(CH3)- A-138. CH3 () 4-CH3O-phenyl-CH(CH3)- A-139. CH3 (R) 4-Ch3O-phenyl-CH(CH3)- A-140. CH3 (S) 4-CH3O-phenyl-CH(CH3)- A-141. CH3 () 4-H5C2-O-phenyl-CH (CH3)- A-142. CH3 (R) 4-H5C2-O-phenyl-CH (CH3)- A-143. CH3 (S) 4-H5C2-O-phenyl-CH (CH3)- A-144. CH3 () 4-n-propoxy-phenyl-CH (CH3)- A-145. CH3 (R) 4-n-propoxy-phenyl-CH(CH3)- A-146. CH3 (S) 4-n-propoxy-phenyl-CH(CH3)- A-147. CH3 (~ 4-n-butoxy-phenyl-CH(CH3)- A-148. CH3 (R) 4-n-butoxyx-phenyl-CH(CH3)- A-149. CH3 (S) 4-n-nbutoxyphenyl-CH(CH3)- A-150. CH3 () 4-tert-butoxy-phenyl-CH(CH3)- A-151. CH3 (R) 4-tert-butoxyx-phenyl-CH(CH3)- A-152. CH3 (S) 4-tert-butoxyphenyl-CH(CH3)- A-153. CH3 () 4-CH3-phenyl-CH(CH3)- A-154. CH3 (R) 4-CH3-phenyl-CH(CH3)- A-155. CH3 (S) 4-CH3-phenyl-CH(CH3)- A-156. CH3 () 4-C2H5-phenyl-CH(CH3)- A-157. CH3 (R) 4-C2H5-phenyl-CH(CH3)- A-158. CH3 (S) 4-C2H5-phenyl-CH(CH3)- A-159. CH3 () 4-n-C3H7-phenyl-CH(CH3)- A-160. CH3 (R) 4-n-C3H7-phenyl-CH(CH3)- A-161. CH3 (S) 4-n-C3H7-phenyl-CH(CH3)- A-162. CH3 () 4-iso-C3H7-phenyl-CH (CH3)- A-163. CH3 (R) 4-iso-C3H7-phenyl-CH (CH3)- A-164. CH3 (S) 4-iso-C3H7-phenyl-CH (CH3)- A-165. CH3 (~) 4-n-C4H9-phenyl-CH(CH3)- A-166. CH3 (R) 4-n-C4Hg-phenyl-CH (CH3)- A-167. CH3 (S) 4-n-C4H9-phenyl-CH(CH3)- A-168. CH3 (~) 4-tert-C4H9-phenyl-CH(CH3)- A-169. CH3 (R) 4-tert-C4H9-phenyl-CH (CH3)- A-170. CH3 (S) 4-tert-C4H9-phenyl-CH (CH3)- A-171. CH3 (~) 4-cycl.-C6H11-phenyl-CH(CH3)- A-172. CH3 R) 4-cycl.-C6H11-phenyl-CH(CH3)- No. R2 R4 A-173. CH3 S) 4-cycl.-C6H11-phenyl-CH(CH3)- A-174. CH3 (~) 4-OCF3-phenyl-CH(CH3)- A-175. CH3 (R) 4-OCF3-phenyl-CH(CH3)- A-176. CH3 (S) 4-OCF3-phenyl-CH(CH3)- A-177. CH3 () 4-CF3-phenyl-CH (CH3)- A-178. CH3 (R) 4-CF3-phenyl-CH (CH3)- A-179. CH3 (S) 4-CF3-phenyl-CH (CH3)- A-180. CH3 () 3-F-phenyl-CH(CH3)- A-181. CH3 (R) 3-F-phenyl-CH(CH3)- A-182. CH3 (S) 3-F-phenyl-CH(CH3)- A-183. CH3 () 3-Cl-phenyl-CH(CH3)- A-184. CH3 (R) 3-CI-phenyl-CH (CH3)- A-185. CH3 (S) 3-CI-phenyl-CH (CH3)- A-186. CH3 () 3-Br-phenyl-CH(CH3)- A-187. CH3 (R) 3-Br-phenyl-CH (CH3)- A-188. CH3 (S) 3-Br-phenyl-CH (CH3)- A-189. CH3 ~) 3-CF3-phenyl-CH(CH3)- A-190. CH3 (R) 3-CF3-phenyl-CH (CH3)- A-191. CH3 (S) 3-CF3-phenyl-CH (CH3)- A-192. CH3 () 3, 4-F2-phenyl-CH(CH3)- A-193. CH3 (R) 3, 4-F2-phenyl-CH(CH3)- A-194. CH3 (S) 3, 4-F2-phenyl-CH(CH3)- A-195. CH3 () 3, 4-Cl2-phenyl-CH(CH3)- A-196. CH3 (R) 3, 4-Cl2-phenyl-CH(CH3)- A-197. CH3 (S) 3, 4-Cl2-phenyl-CH(CH3)- A-198. CH3 () 3, 4-Br2-phenyl-CH(CH3)- A-199. CH3 (R) 3, 4-Br2-phenyl-CH(CH3)- A-200. CH3 (S) 3, 4-Br2-phenyl-CH(CH3)- A-201. CH3 () 4-Difluoromethoxyphenyl-CH(CH3)- A-202. CH3 (R) 4-Difluoromethoxyphenyl-CH(CH3)- A-203. CH3 (S) 4-Difluoromethoxyphenyl-CH(CH3)- A-204. CH3 () 4-(1, 1,2, 2-tetrafluoroethoxy)phenyl-CH(CH3)- A-205. CH3 (R) 4-(1, 1,2, 2-tetrafluoroethoxy) henyl-CH(CH3)- A-206. CH3 (S) 4-(1, 1,2, 2-tetrafluoroethoxy) henyl-CH(CH3)- A-207. CH3 () (5, 5,7, 7-tetramethylindan-2-yl)-CH(CH3)- A-208. CH3 (R) (5, 5,7, 7-tetramethylindan-2-yl)-CH(CH3)- A-209. CH3 (S) (5, 5,7, 7-tetramethylindan-2-yl)-CH(CH3)- A-210. CH3 () (1,1, 4, 4,-tetramethyl-1, 2,3, 4- tetrahydronaphthalin-6-yl)-CH (CH3)- A-211. CH3 (R) (1,1, 4, 4,-tetramethyl-1, 2,3, 4- tetrahydronaphthalin-6-yl)-CH(CH3)- No. R2 R4 A-212. CH3 (S) (1,1, 4, 4,-tetramethyl-1, 2,3, 4- tetrahydronaphthalin-6-yl)-CH (CH3)- A-213. CH3 () (1, 1-dimethyl-1, 2,3, 4-tetrahydronaphthalin-6- yl)-CH(CH3)- A-214. CH3 (R) (1, 1-dimethyl-1, 2,3, 4-tetrahydronaphthalin-6- yl)-CH CH3)- A-215. CH3 (S) (1, 1-dimethyl-1, 2,3, 4-tetrahydronaphthalin-6- l)-CH (CH3)- A-216. CH3 () (1,1, 4,4, 7-pentamethyl-1, 2,3, 4- tetrahydronaphthalin-6-yl)-CH(CH3)- A-217. CH3 (R) (1,1, 4,4, 7-pentamethyl-1, 2,3, 4- tetrahydronaphthalin-6-yl)-CH(CH3)- A-218. CH3 (S) (1,1, 4,4, 7-pentamethyl-1, 2,3, 4- tetrahydronaphthalin-6-yl)-CH(CH3)- A-219. CH3 () (1,1, 7-trimethyl-1, 2,3, 4-tetrahydronaphthalin-6- l)-CH(CH3)- A-220. CH3 (R) (1,1, 7-trimethyl-1, 2,3, 4-tetrahydronaphthalin- 6-yl)-CH (CH3)- A-221. CH3 (S) (1,1, 7-trimethyl-1, 2,3, 4-tetrahydronaphthalin- 6-yl)-CH (CH3)- A-222. CH3 ~ (2-methyl-1, 3-dioxan-2-yl)-CH (CH3)- A-223. CH3 (R) 2-methyl-1, 3-dioxan-2-yl)-CH (CH3)- A-224. CH3 (S) 2-methyl-1, 3-dioxan-2-yl)-CH (CH3)- A-225. CH3 () (2, 5, 5-trimethyl-1,3-dioxan-2-yl)-CH(CH3)- A-226. CH3 (R) 2,5, 5-trimethyl-1, 3-dioxan-2-yl)-CH (CH3)- A-227. CH3 S) 2, 5, 5-trimethyl-1, 3-dioxan-2-yl)-CH (CH3)- A-228. CH3 () (2, 2-difluorobenzodioxole-5-yl CH (C2H5)- A-229. CH3 (R) (2, 2-difluorobenzodioxole-5-yl CH (C2H5)- A-230. CH3 (S) (2,2-difluorobenzodioxole-5-yl CH (C2H5)- A-231. CH3 C6H5CH2CH2- A-232. CH3 4-F-C6H4CH2CH2- A-233. CH3 4-CI-C6H4CH2CH2- A-234. CH3 4-Br-C6H4CH2CH2- A-235. CH3 4-CH30-C6H4CH2CH2- A-236. CH3 4-C2H50-C6H4CH2CH2- A-237. CH3 4-n-C3H70-C6H4CH2CH2- A-238. CH3 4-n-C4H9O-C6H4CH2CH2- A-239. CH3 4-t-C4H9O-C6H4CH2CH2- A-240. CH3 3, 4-(CH30) 2-C6H4CH2CH2- A-241. CH3 4-H3C-C6H4CH2CH2- A-242. CH3 4-H3C-H2C-C6H4CH2CH2- A-243. CH3 4-H3C-H2C-H2C-C6H4CH2CH2- No. R2 R4 A-244. CH3 4-H3C-H2C-H2C-H2C-C6H4CH2CH2- A-245. CH3 4-(CH3)3C-C6H4CH2CH2- A-246. CH3 4-F3CO-C6H4CH2CH2- A-247. CH3 4-F3C-C6H4CH2CH2- A-248. CH3 3-F3C-C6H4CH2CH2- A-249. CH3CH2 4-CH3-cyclohexyl- A-250. CH3CH2 cis-4-CH3-cyclohexyl- A-251. CH3CH2 trans-4-CH3-cyclohexyl- A-252. CH3CH2 4-C2H5-cyclohexyl- A-253. CH3CH2 cis-4-C2H5-cyclohexyl- A-254. CH3CH2 trans-4-C2H5-cyclohexyl- A-255. CH3CH2 4-n-propyl-cyclohexyl- A-256. CH3CH2 cis-4-n-propyl-cyclohexyl- A-257. CH3CH2 trans-4-n-propyl-cyclohexyl- A-258. CH3CH2 4-isopropyl-cyclohexyl- A-259. CH3CH2 cis-4-isopropyl-cyclohexyl- A-260. CH3CH2 trans-4-isopropyl-cyclohexyl- A-261. CH3CH2 4-n-butylcyclohexyl- A-262. CH3CH2 cis-4-n-butylcyclohexyl- A-263. CH3CH2 trans-4-n-butylcyclohexyl- A-264. CH3CH2 4-(2-butyl) cyclohexyl- A-265. CH3CH2 cis-4- (2-butyl) cyclohexyl- A-266. CH3CH2 trans-4- (2-butyl) cyclohexyl- A-267. CH3CH2 4-tert-butylcyclohexyl- A-268. CH3CH2 cis-4-tert-butylcyclohexyl- A-269. CH3CH2 trans-4-tert-butylcyclohexyl- A-270. CH3CH2 4-(cyclohexyl-C(CH3)2)-cyclohexyl- A-271. CH3CH2 cis-4- (cyclohexyl-C (CH3) 2)-cyclohexyl- A-272. CH3CH2 trans-4-(cyclohexyl-C(CH3)2)-cyclohexyl- A-273. CH3CH2 C6H5- A-274. CH3CH2 4-F-C6H4- A-275. CH3CH2 4-Cl-C6H4- A-276. CH3CH2 4-Br-C6H4- A-277. CH3CH2 4-(C6H5)-C6H4- A-278. CH3CH2 4-phenoxyphenyl A-279. CH3CH2 benzyl A-280. CH3CH2 4-CH3-C6H4-CH2- A-281. CH3CH2 4-C2H5-C6H4-CH2- A-282. CH3CH2 4-n-C3H7-C6H4-CH2- A-283. CH3CH2 4-isopropyl-C6H4-CH2- A-284. CH3CH2 4-n-C4H9-C6H4-CH2- No. R2 R4 A-285. CH3CH2 4-isobutyl-C6H4-CH2- A-286. CH3CH2 4-tert-buyl-C6H4CH2- A-287. CH3CH2 4-F3C-C6H4CH2- A-288. CH3CH2 4-methoxy-C6H4CH2- A-289. CH3CH2 4-ethoxy-C6H4CH2- A-290. CH3CH2 4-n-propoxy-C6H4CH2- A-291. CH3CH2 4-isopropoxy-C6H4CH2- A-292. CH3CH2 4-n-butoxy-C6H4CH2- A-293. CH3CH2 4-tert-butoxy-C6H4CH2- A-294. CH3CH2 4-F-C6H4CH2- A-295. CH3CH2 4-Cl-C6H4CH2- A-296. CH3CH2 4-Br-C6H4CH2- A-297. CH3CH2 3,4-F2-C6H3CH2- A-298. CH3CH2 3, 4-CI2-C6H3CH2- A-299. CH3CH2 3, 4-Br2-C6H3CH2- A-300. CH3CH2 4-(4-CH3-C6H4-O)-C6H4-CH2- A-301. CH3CH2 4-(4-C2H5-C6H4-O)-C6H4-CH2- A-302. CH3CH2 4-(4-n-C3H7-C6H4-O)-C6H4-CH2- A-303. CH3CH2 4-(4-iso-C3H7-C6H4-O)-C6H4-CH2- A-304. CH3CH2 4- (4-n-C4H9-C6H4-0)-C6H4-CH2- A-305. CH3CH2 4-(4-iso-C4H9-C6H4-O)-C6H4-CH2- A-306. CH3CH2 4-(4-tert-C4H9-C6H4-O)-C6H4-CH2- A-307. CH3CH2 4- (4-H3C-0-C6H4-0)-C6H4-CH2- A-308. CH3CH2 4-(4-H3C-H2C-O-C6H4-O)-C6H4-CH2- A-309. CH3CH2 4- (4-H3C-H2C-H2C-0-C6H4-0)-C6H4-CH2- A-310. CH3CH2 4-(4-H3C-H2C-H2C-H2C-O-C6H4-O)-C6H4-CH2- A-311. CH3CH2 4-(4-tert-butoxy-C6H4-O)-C6H4-CH2- A-312. CH3CH2 4-(4-Cl-C6H4-O)-C6H4-CH2- A-313. CH3CH2 4-(4-Br-C6H4-O)-C6H4-CH2- A-314. CH3CH2 4-(3-CH3-C6H4-O)-C6H4-CH2- A-315. CH3CH2 4-(3-C2H5-C6H4-O)-C6H4-CH2- A-316. CH3CH2 4-(3-n-C3H7-C6H4-O)-C6H4-CH2- A-317. CH3CH2 4-(3-iso-C3H7-C6H4-O)-C6H4-CH2- A-318. CH3CH2 4-(3-n-C4H9-C6H4-O)-C6H4-CH2- A-319. CH3CH2 4- (3-iso-C4H9-C6H4-0)-C6H4-CH2- A-320. CH3CH2 4-(3-tert-butyl-C6H4-O)-C6H4-CH2- A-321. CH3CH2 4- (3-H3C-O-C6H4-O)-C6H4-CH2- A-322. CH3CH2 4-(3-H3C-H2C-O-C6H4-O)-C6H4-CH2- A-323. CH3CH2 4-(3-H3C-H2C-H2C-O-C6H4-O)-C6H4-CH2- A-324. CH3CH2 4-(3-H3C-H2C-H2C-H2C-O-C6H4-O)-C6H4-CH2- A-325. CH3CH2 4-(3-tert-butoxy-C6H4-O)-C6H4-CH2- No. R2 R4 A-326. CH3CH2 4-(3-F-C6H4-O)-C6H4-CH2- A-327. CH3CH2 4-(3-Cl-C6H4-O)-C6H4-CH2- A-328. CH3CH2 4-(3-Br-C6H4-O)-C6H4-CH2- A-329. CH3CH2 4- (2-CH3-C6H4-0)-C6H4-CH2- A-330. CH3CH2 4- (2-C2H5-C6H4-0)-C6H4-CH2- A-331. CH3CH2 4- (2-n-C3H7-C6H4-0)-C6H4-CH2- A-332. CH3CH2 4-(2-iso-C3H7-C6H4-O)-C6H4-CH2- A-333. CH3CH2 4-(2-n-C4HY9-C6H4-O)-C6H4-CH2- A-334. CH3CH2 4-(2-iso-C4H9-C6H4-O)-C6H4-CH2- A-335. CH3CH2 4-(2-tert-butyl-C6H4-O)-C6H4-CH2- A-336. CH3CH2 4- (2-H3C-0-C6H4-0)-C6H4-CH2- A-337. CH3CH2 4-(2-H3C-H2C-O-C6H4-O)-C6H4-CH2- A-338. CH3CH2 4- (2-H3C-H2C-H2C-0-C6H4-0)-C6H4-CH2- A-339. CH3CH2 4-(2-H3C-H2C-H2C-H2C-O-C6H4-O)-C6H4-CH2- A-340. CH3CH2 4-(2-tert-butoxy-C6H4-O)-C6H4-CH2- A-341. CH3CH2 4- (2-F-C6H4-0)-C6H4-CH2- A-342. CH3CH2 4-(2-Cl-C6H4-O)-C6H4-CH2- A-343. CH3CH2 4- (2-Br-C6H4-0)-C6H4-CH2- A-344. CH3CH2 4-(3,4-F2-C6H3-O)-C6H4-CH2- A-345. CH3CH2 4-(3,4-Cl2-C6H3-O)-C6H4-CH2- A-346. CH3CH2 4-(3,4-(CH3)2-C6H3-O)-C6H4-CH2- A-347. CH3CH2 4- (3-F-4-Cl-C6H3-0)-C6H4-CH2- A-348. CH3CH2 4-(3-Cl-4-F-C6H3-O)-C6H4-CH2- A-349. CH3CH2 4-(3-CH3-4-ClC6H3-O)-C6H4-CH2- A-350. CH3CH2 4- (3-CI-4-CH3-C6H3-O)-C6H4-CH2- A-351. CH3CH2 4-(3-CI-4-Br-C6H3-O)-C6H4-CH2- A-352. CH3CH2 4-(3-CH3-4-Br-C6H3-O)-C6H4-CH2- A-353. CH3CH2 () henyl-CH(CH3)- A-354. CH3CH2 (R) henyl-CH(CH3)- A-355. CH3CH2 (S) henyl-CH(CH3)- A-356. CH3CH2 () 4-F-phenyl-CH(CH3)- A-357. CH3CH2 (R) 4-F-phenyl-CH(CH3)- A-358. CH3CH2 (S) 4-F-phenyl-CH(CH3)- A-359. CH3CH2 () 4-CI-phenyl-CH (CH3)- A-360. CH3CH2 (R) 4-CI-phenyl-CH (CH3)- A-361. CH3CH2 (S) 4-CI-phenyl-CH (CH3)- A-362. CH3CH2 (~ 4-Br-phenyl-CH(CH3)- A-363. CH3CH2 (R) 4-Br-phenyl-CH(CH3)- A-364. CH3CH2 (S) 4-Br-phenyl-CH(CH3)- A-365. CH3CH2 () 4-Cl-2-F-phenyl-CH(CH3)- A-366. CH3CH2 (R) 4-CI-2-F-phenyl-CH (CH3) - No. R2 R4 A-367. CH3CH2 (S) 4-Cl-2-F-phenyl-CH(CH3)- A-368. CH3CH2 ~) 6-Cl-2-F-phenyl-CH(CH3)- A-369. CH3CH2 (R) 6-CI-2-F-phenyl-CH (CH3)- A-370. CH3CH2 (S) 6-CI-2-F-phenyl-CH (CH3)- A-371. CH3CH2 ~) 2-F-phenyl-CH(CH3)- A-372. CH3CH2 (R) 2-F-phenyl-CH(CH3)- A-373. CH3CH2 (S) 2-F-phenyl-CH(CH3)- A-374. CH3CH2 (S) 2, 4-F2-phenyl-CH(CH3)- A-375. CH3CH2 () 2, 4-F2-phenyl-CH(CH3)- A-376. CH3CH2 (R) 2, 4-F2-phenyi-CH (CH3)- A-377. CH3CH2 (S) 2, 5-F2-phenyl-CH(CH3)- A-378. CH3CH2 () 2, 5-F2-phenyl-CH(CH3)- A-379. CH3CH2 (R) 2, 5-F2-phenyl-CH(CH3)- A-380. CH3CH2 (S) 2, 6-F2-phenyl-CH(CH3)- A-381. CH3CH2 () 2, 6-F2-phenyl-CH(CH3)- A-382. CH3CH2 R) 2,6-F2-phenyl-CH(CH3)- A-383. CH3CH2 () 2-CH3O-phenyl-CH(CH3)- A-384. CH3CH2 (R) 2-CH30-phenyl-CH (CH3)- A-385. CH3CH2 (S) 2-CH30-phenyl-CH (CH3)- A-386. CH3CH2 () 4-CH30-phenyl-CH (CH3)- A-387. CH3CH2 (R) 4-CH3O-phenyl-CH(CH3)- A-388. CH3CH2 (S) 4-CH3O-phenyl-CH(CH3)- A-389. CH3CH2 () 4-H5C2-O-phenyl-CH (CH3)- A-390. CH3CH2 (R) 4-H5C2-O-phenyl-CH (CH3)- A-391. CH3CH2 (S) 4-H5C2-O-phenyl-CH (CH3)- A-392. CH3CH2 () 4-n-propoxy-phenyl-CH(CH3)- A-393. CH3CH2 (R) 4-n-propoxy-phenyl-CH(CH3)- A-394. CH3CH2 (S) 4-n-propoxy-phenyl-CH(CH3)- A-395. CH3CH2 () 4-n-butoxy-phenyl-CH(CH3)- A-396. CH3CH2 (R) 4-n-butoxyx-phenyl-CH(CH3)- A-397. CH3CH2 (S) 4-n-butoxyphenyl-CH(CH3)- A-398. CH3CH2 () 4-tert-butoxy-phenyl-CH(CH3)- A-399. CH3CH2 (R) 4-tert-butoxyx-phenyl-CH(CH3)- A-400. CH3CH2 (S) 4-tert-butoxyphenyl-CH(CH3)- A-401. CH3CH2 () 4-CH3-phenyl-CH(CH3)- A-402. CH3CH2 (R) 4-CH3-phenyl-CH(CH3)- A-403. CH3CH2 (S) 4-CH3-phenyl-CH(CH3)- A-404. CH3CH2 () 4-C2H5-phenyl-CH(CH3)- A-405. CH3CH2 (R) 4-C2H5-phenyl-CH (CH3)- A-406. CH3CH2 (S) 4-C2H5-phenyl-CH(CH3)- A-407. CH3CH2 () 4-n-C3H7-phenyl-CH(CH3)- No. R2 R4 A-408. CH3CH2 (R) 4-n-C3H7-phenyl-CH(CH3)- A-409. CH3CH2 (S) 4-n-C3H7-phenyl-CH (CH3)- A-410. CH3CH2 (~ 4-iso-C3H7-phenyl-CH (CH3)- A-411. CH3CH2 (R) 4-iso-C3H7-phenyl-CH(CH3)- A-412. CH3CH2 (S) 4-iso-C3H7-phenyl-CH(CH3)- A-413. CH3CH2 () 4-n-C4H9-phenyl-CH (CH3)- A-414. CH3CH2 (R) 4-n-C4H9-phenyl-CH (CH3)- A-415. CH3CH2 (S) 4-n-C4H9-phenyl-CH (CH3)- A-416. CH3CH2 () 4-tert-C4H9-phenyl-CH (CH3)- A-417. CH3CH2 (R) 4-tert-C4H9-phenyl-CH(CH3)- A-418. CH3CH2 (S) 4-tert-C4H9-phenyl-CH(CH3)- A-419. CH3CH2 () 4-cycl.-C6H11-phenyl-CH(CH3)- A-420. CH3CH2 (R) 4-cycl.-C6H11-phenyl-CH (CH3)- A-421. CH3CH2 (S) 4-cycl.-C6H11-phenyl-CH (CH3)- A-422. CH3CH2 () 4-OCF3-phenyl-CH(CH3)- A-423. CH3CH2 (R) 4-OCF3-phenyl-CH(CH3)- A-424. CH3CH2 (S) 4-OCF3-phenyl-CH(CH3)- A-425. CH3CH2 () 4-CF3-phenyl-CH(CH3)- A-426. CH3CH2 (R) 4-CF3-phenyl-CH(CH3)- A-427. CH3CH2 (S) 4-CF3-phenyl-CH(CH3)- A-428. CH3CH2 (~ 3-F-phenyl-CH(CH3)- A-429. CH3CH2 (R) 3-F-phenyl-CH(CH3)- A-430. CH3CH2 (S) 3-F-phenyl-CH(CH3)- A-431. CH3CH2 () 3-Cl-phenyl-CH(CH3)- A-432. CH3CH2 (R) 3-CI-phenyl-CH (CH3)- A-433. CH3CH2 (S) 3-Cl-phenyl-CH(CH3)- A-434. CH3CH2 () 3-Br-phenyl-CH(CH3)- A-435. CH3CH2 (R) 3-Br-phenyl-CH(CH3)- A-436. CH3CH2 (S) 3-Br-phenyl-CH(CH3)- A-437. CH3CH2 () 3-CF3-phenyl-CH(CH3)- A-438. CH3CH2 (R) 3-CF3-phenyl-CH(CH3)- A-439. CH3CH2 (S) 3-CF3-phenyl-CH(CH3)- A-440. CH3CH2 () 3, 4-F2-phenyl-CH(CH3)- A-441. CH3CH2 (R) 3, 4-F2-phenyl-CH(CH3)- A-442. CH3CH2 (S) 3, 4-F2-phenyl-CH(CH3)- A-443. CH3CH2 ~ 3, 4-Cl2-phenyl-CH(CH3)- A-444. CH3CH2 (R) 3, 4-Cl2-phenyl-CH(CH3)- A-445. CH3CH2 (S) 3, 4-Cl2-phenyl-CH(CH3)- A-446. CH3CH2 () 3, 4-Br2-phenyl-CH(CH3)- A-447. CH3CH2 (R) 3, 4-Br2-phenyl-CH(CH3)- A-448. CH3CH2 (S) 3, 4-Br2-phenyl-CH(CH3)- No. R2 R4 A-449. CH3CH2 () 4-Difluoromethoxyphenyl-CH (CH3)- A-450. CH3CH2 (R) 4-Difluoromethoxyphenyl-CH (CH3)- A-451. CH3CH2 (S) 4-Difluoromethoxyphenyl-CH (CH3)- A-452. CH3CH2 () 4-(1, 1,2, 2-tetrafluoroethoxy) phenyl-CH (CH3)- A-453. CH3CH2 R 4-(1,1, 2, 2-tetrafluoroethoxy) phenyl-CH (CH3)- A-454. CH3CH2 (S) 4-(1, 1,2, 2-tetrafluoroethoxy) phenyl-CH (CH3)- A-455. CH3CH2 () (5, 5,7, 7-tetramethylindan-2-yl)-CH(CH3)- A-456. CH3CH2 (R) (5, 5,7, 7-tetramethylindan-2-yl)-CH(CH3)- A-457. CH3CH2 (S) (5, 5,7, 7-tetramethylindan-2-yl)-CH(CH3)- A-458. CH3CH2 () (1,1, 4, 4,-tetramethyl-1, 2,3, 4- tetrahydronaphthalin-6-yl)-CH (CH3)- A-459. CH3CH2 (R) (1,1, 4, 4,-tetramethyl-1, 2,3, 4- tetrahydronaphthalin-6-yl)-CH (CH3)- A-460. CH3CH2 (S) (1,1, 4, 4,-tetramethyl-1, 2,3, 4- tetrahydronaphthalin-6-yl)-CH(CH3)- A-461. CH3CH2 () (1, 1-dimethyl-1, 2,3, 4-tetrahydronaphthalin-6- l)-CH(CH3)- A-462. CH3CH2 (R) (1, 1-dimethyl-1, 2,3, 4-tetrahydronaphthalin-6- l)-CH(CH3)- A-463. CH3CH2 (S) (1, 1-dimethyl-1, 2,3, 4-tetrahydronaphthalin-6- yl-CH CH3)- A-464. CH3CH2 () (1,1, 4,4, 7-pentamethyl-1, 2,3, 4- tetrahydronaphthalin-6-yl)-CH (CH3)- A-465. CH3CH2 (R) (1,1, 4,4, 7-pentamethyl-1, 2,3, 4- tetrahydronaphthalin-6-yl)-CH (CH3)- A-466. CH3CH2 (S) (1,1, 4, 4, 7-pentamethyl-1, 2,3, 4- tetrahydronaphthalin-6-yl)-CH (CH3)- A-467. CH3CH2 () (1,1, 7-trimethyl-1, 2,3, 4-tetrahydronaphthalin-6- l)-CH (CH3)- A-468. CH3CH2 (R) (1,1, 7-trimethyl-1, 2,3, 4-tetrahydronaphthalin- 6-yl)-CH (CH3)- A-469. CH3CH2 (S) (1,1, 7-trimethyl-1, 2,3, 4-tetrahydronaphthalin- 6-yl)-CH(CH3)- A-470. CH3CH2 () (2-methyl-1, 3-dioxan-2-yl)-CH (CH3)- A-471. CH3CH2 (R) 2-methyl-1,3-dioxan-2-yl)-CH(CH3)- A-472. CH3CH2 (S) 2-methyl-1, 3-dioxan-2-yl)-CH (CH3)- A-473. CH3CH2 () (2, 5, 5-trimethyl-1,3-dioxan-2-yl)-CH (CH3) - A-474. CH3CH2 (R) 2,5, 5-trimethyl-1,3-dioxan-2-yl)-CH(CH3)- A-475. CH3CH2 (S) 2,5, 5-trimethyl-1,3-dioxan-2-yl)-CH(CH3)- A-476. CH3CH2 () (2, 2-difluorobenzodioxole-5-yl CH (C2H5)- A-477. CH3CH2 (R) (2, 2-difluorobenzodioxole-5-yl) CH (C2H5)- A-478. CH3CH2 (S) (2, 2-difluorobenzodioxole-5-yl)CH(C2H5)- No. R2 R4 A-479. CH3CH2 C6H5CH2CH2- A-480. CH3CH2 4-F-C6H4CH2CH2- A-481. CH3CH2 4-Cl-C6H4CH2CH2 A-482. CH3CH2 4-Br-C6H4CH2CH2- A-483. CH3CH2 4-CH30-C6H4CH2CH2- A-484. CH3CH2 4-C2H50-C6H4CH2CH2- A-485. CH3CH2 4-n-C3H70-C6H4CH2CH2- A-486. CH3CH2 4-n-C4H90-C6H4CH2CH2- A-487. CH3CH2 4-t-C4H9O-C6H4CH2CH2- A-488. CH3CH2 3,4-(CH3O)2-C6H4CH2CH2- A-489. CH3CH2 4-H3C-C6H4CH2CH2- A-490. CH3CH2 4-H3C-H2C-C6H4CH2CH2- A-491. CH3CH2 4-H3C-H2C-H2C-C6H4CH2CH2- A-492. CH3CH2 4-H3C-H2C-H2C-H2C-C6H4CH2CH2- A-493. CH3CH2 4-(CH3) 3C-C6H4CH2CH A-494. CH3CH2 4-F3CO-C6H4CH2CH2- A-495. CH3CH2 4-F3C-C6H4CH2CH2- A-496. CH3CH2 3-F3C-C6H4CH2CH2- A-497. CH3CHF 4-CH3-cyclohexyl- A-498. CH3CHF cis-4-CH3-cyclohexyl- A-499. CH3CHF trans-4-CH3-cyclohexyl- A-500. CH3CHF 4-C2H5-cyclohexyl- A-501. CH3CHF cis-4-C2H5-cyclohexyl- A-502. CH3CHF trans-4-C2H5-cyclohexyl- A-503. CH3CHF 4-n-propyl-cyclohexyl- A-504. CH3CHF cis-4-n-propyl-cyclohexyl- A-505. CH3CHF trans-4-n-propyl-cyclohexyl- A-506. CH3CHF 4-isopropyl-cyclohexyl- A-507. CH3CHF cis-4-isopropyl-cyclohexyl- A-508. CH3CHF trans-4-isopropyl-cyclohexyl- A-509. CH3CHF 4-n-butylcyclohexyl- A-510. CH3CHF cis-4-n-butylcyclohexyl- A-511. CH3CHF trans-4-n-butylcyclohexyl- A-512. CH3CH F 4-tert-butylcyclohexyl- A-513. CH3CHF cis-4-tert-butylcyclohexyl- A-514. CH3CHF trans-4-tert-butylcyclohexyl- A-515. CH3CHF 4- (2-butyl) cyclohexyl- A-516 CH3CHF cis-4-(2-butyl)cyclohexyl- A-517. CH3CHF trans-4-(2-butyl)cyclohexyl- A-518. CH3CHF 4- (cyclohexyl-C (CH3) 2)-cyclohexyl- A-519. CH3CHF cis-4- (cyclohexyl-C (CH3) 2)-cyclohexyl- No. R2 R4 A-520. CH3CHF trans-4- (cyclohexyl-C (CH3) 2)-cyclohexyl- A-521. CH3CHF C6H5- A-522. CH3CHF 4-F-C6H4- A-523. CH3CHF 4-CI-C6H4- A-524. CH3CHF 4-Br-C6H4- A-525. CH3CHF 4- (C6H5)-C6H4- A-526. CH3CHF 4-phenoxyphenyl A-527. CH3CHF benzyl A-528. CH3CHF 4-CH3-C6H4-CH2- A-529. CH3CHF 4-C2H5-C6H4-CH2- A-530. CH3CHF 4-n-C3H7-C6H4-CH2- A-531. CH3CHF 4-isopropyl-C6H4-CH2- A-532. CH3CHF 4-n-C4H9-C6H4-CH2- A-533. CH3CHF 4-isobutyl-C6H4-CH2- A-534. CH3CHF 4-tert-buyl-C6H4CH2- A-535. CH3CHF 4-F3C-C6H4CH2- A-536. CH3CHF 4-methoxy-C6H4CH2- A-537. CH3CHF 4-ethoxy-C6H4CH2- A-538. CH3CHF 4-n-propoxy-C6H4CH2- A-539. CH3CHF 4-isopropoxy-C6H4CH2- A-540. CH3CHF 4-n-butoxy-C6H4CH2- A-541. CH3CHF 4-tertbutoxy-C6H4CH2- A-542. CH3CHF 4-F-C6H4CH2- A-543. CH3CHF 4-CI-C6H4CH2- A-544. CH3CHF 4-Br-C6H4CH2- A-545. CH3CHF 3,4-F2-C6H3CH2- A-546. CH3CHF 3, 4-CI2-C6H3CH2- A-547. CH3CHF 3, 4-Br2-C6H3CH2- A-548. CH3CHF 4- (4-CH3-C6H4-0)-C6H4-CH2- A-549. CH3CHF 4-(4-C2H5-C6H4-O)-C6H4-CH2- A-550. CH3CHF 4-(4-n-C3H7-C6H4-O)-C6H4-CH2- A-551. CH3CHF 4-(4-iso-C3H7-C6H4-O)-C6H4-CH2- A-552. CH3CHF 4-(4-n-C4H9-C6H4-O)-C6H4-CH3- A-553. CH3CH F 4- (4-iso-C4H9-C6H4-0)-C6H4-CH2- A-554. CH3CHF 4- (4-tert-C4H9-C6H4-0)-C6H4-CH2- A-555. CH3CHF 4-(4-H3C-O-C6H4-O)-C6H4-CH2- A-556. CH3CHF 4-(4-H3C-H2C-O-C6H4-O)-C6H4-CH2- A-557. CH3CHF 4-(4-H3C-H2C-H2C-O-C6H4-O)-C6H4-CH2- A-558. CH3CHF 4-(4-H3C-H2C-H2C-H2C-O-C6H4-O)-C6H4-CH2- A-559. CH3CHF 4- (4-tert-butoxy-C6H4-0)-C6H4-CH2- A-560. CH3CHF 4-(4-Cl-C6H4-O)-C6H4-CH2- No. R2 R4 A-561. CH3CHF 4-(4-Br-C6H4-O)-C6H4-CH2- A-562. CH3CHF 4-(3-CH3-C6H4-O)-C6H4-CH2- A-563. CH3CHF 4- (3-C2H5-C6H4-0)-C6H4-CH2- A-564. CH3CHF 4-(3-n-C3H7-C6H4-O)-C6H4-CH2- A-565. CH3CHF 4-(3-iso-C3H7-C6H4-O)-C6H4-CH2- A-566. CH3CHF 4- (3-n-C4H9-C6H4-0)-C6H4-CH2- A-567. CH3CHF 4-(3-iso-C4H9-C6H4-O)-C6H4-CH2- A-568. CH3CHF 4- (3-tert-butyl-C6H4-0)-C6H4-CH2- A-569. CH3CHF 4- (3-H3C-0-C6H4-0)-C6H4-CH2- A-570. CH3CHF 4-(3-H3C-H2C-O-C6H4-O)-C6H4-CH2- A-571. CH3CHF 4-(3-H3C-H2C-H2C-O-C6H4-O)-C6H4-CH2- A-572. CH3CHF 4- (3-H3C-H2C-H2C-H2C-0-C6H4-0)-C6H4-CH2- A-573. CH3CHF 4- (3-tert-butoxy-C6H4-O)-C6H4-CH2- A-574. CH3CHF 4- (3-F-C6H4-0)-C6H4-CH2- A-575. CH3CHF 4-(3-Cl-C6H4-O)-C6H4-CH2- A-576. CH3CHF 4-(3-Br-C6H4-O)-C6H4-CH2- A-577. CH3CHF 4- (2-CH3-C6H4-0)-C6H4-CH2- A-578. CH3CHF 4- (2-C2H5-C6H4-0)-C6H4-CH2- A-579. CH3CHF 4-(2-n-C3H7-C6H4-O)-C6H4-CH2 A-580. CH3CHF 4-(2-iso-C3H7-C6H4-O)-C6H4-CH2- A-581. CH3CHF 4- (2-n-C4H9-C6H4-0)-C6H4-CH2- A-582. CH3CHF 4- (2-iso-C4H9-C6H4-O)-C6H4-CH2- A-583. CH3CHF 4- (2-tert-butyl-C6H4-0)-C6H4-CH2- A-584. CH3CHF 4-(2-H3C-O-C6H4-O)-C6H4-CH2- A-585. CH3CHF 4- (2-H3C-H2C-O-C6H4-O)-C6H4-CH2- A-586. CH3CHF 4- (2-H3C-H2C-H2C-0-C6H4-O)-C6H4-CH2- A-587. CH3CHF 4- (2-H3C-H2C-H2C-H2C-O-C6H4-0)-C6H4-CH2- A-588. CH3CHF 4-(2-tert-butoxy-C6H4-O)-C6H4-CH2- A-589. CH3CHF 4- (2-F-C6H4-0)-C6H4-CH2- A-590. CH3CHF 4-(2-Cl-C6H4-O)-C6H4-CH2- A-591. CH3CHF 4- (2-Br-C6H4-0)-C6H4-CH2- A-592. CH3CHF 4-(3,4-F2-C6H3-O)-C6H4-CH2- A-593. CH3CH F 4-(3, 4-CI2-C6H3-O)-C6H4-CH2- A-594. CH3CHF 4- (3, 4- (CH3) 2-C6H3-0)-C6H4-CH2- A-595. CH3CHF 4- (3-F-4-Cl-C6H3-0)-C6H4-CH2- A-596. CH3CH F 4-(3-CI-4-F-C6H3-O)-C6H4-CH2- A-597. CH3CHF 4-(3-CH3-4-Cl-C6H3-O)-C6H4-CH2- A-598. CH3CHF 4-(3-CI-4-CH3-C6H3-O)-C6H4-CH2- A-599. CH3CHF 4- (3-CI-4-Br-C6H3-0)-C6H4-CH2- A-600. CH3CHF 4-(3-CH3-4-Br-C6H3-O)-C6H40CH2- A-601. CH3CHF ~ phenyl-CH (CH3)- No. R2 R4 A-602. CH3CHF (R) phenyl-CH(CH3)- A-603. CH3CHF (S) phenyl-CH(CH3)- A-604. CH3CHF () 4-F-phenyl-CH(CH3)- A-605. CH3CHF (R) 4-F-phenyl-CH(CH3)- A-606. CH3CHF (S) 4-F-phenyl-CH(CH3)- A-607. CH3CHF () 4-CI-phenyl-CH (CH3)- A-608. CH3CHF (R) 4-CI-phenyl-CH (CH3)- A-609. CH3CHF (S) 4-CI-phenyl-CH (CH3)- A-610. CH3CHF (~) 4-Br-phenyl-CH(CH3)- A-611. CH3CHF (R) 4-Br-phenyl-CH(CH3)- A-612. CH3CHF (S) 4-Br-phenyl-CH(CH3)- A-613. CH3CHF (~) 4-Cl-2-F-phenyl-CH(CH3)- A-614. CH3CHF (R) 4-CI-2-F-phenyl-CH (CH3)- A-615. CH3CHF (S) 4-CI-2-F-phenyl-CH (CH3)- A-616. CH3CHF () 6-Cl-2-F-phenyl-CH(CH3)- A-617. CH3CHF (R) 6-Cl-2-F-phenyl-CH(CH3)- A-618. CH3CHF (S) 6-Cl-2-F-phenyl-CH(CH3)- A-619. CH3CHF () 2-F-phenyl-CH(CH3)- A-620. CH3CHF (R) 2-F-phenyl-CH(CH3)- A-621. CH3CHF (S) 2-F-phenyl-CH(CH3)- A-622. CH3CHF (S) 2, 4-F2-phenyl-CH(CH3)- A-623. CH3CHF () 2, 4-F2-phenyl-CH(CH3)- A-624. CH3CHF (R) 2, 4-F2-phenyl-CH(CH3)- A-625. CH3CHF (S) 2, 5-F2-phenyl-CH(CH3)- A-626. CH3CHF (~) 2,5-F2-phenyl-CH(CH3)- A-627. CH3CHF (R 2, 5-F2-phenyl-CH(CH3)- A-628. CH3CHF (S) 2, 6-F2-phenyl-CH(CH3)- A-629. CH3CHF () 2, 6-F2-phenyl-CH(CH3)- A-630. CH3CHF (R.) 2, 6-F2-phenyl-CH(CH3)- A-631. CH3CHF ~ 2-CH3O-phenyl-CH(CH3)- A-632. CH3CHF (R) 2-CH30-phenyl-CH (CH3)- A-633. CH3CHF (S) 2-CH3O-phenyl-CH(CH3)- A-634. CH3CHF () 4-CH3O-phenyl-CH(CH3)- A-635. CH3CHF (R) 4-CH3O-phenyl-CH(CH3)- A-636. CH3CHF (S) 4-CH30-phenyl-CH (CH3)- A-637. CH3CHF (~) 4-H5C2-O-phenyl-CH(CH3)- A-638. CH3CHF (R) 4-H5C2-O-phenyl-CH (CH3)- A-639. CH3CHF (S) 4-H5C2-O-phenyl-CH(CH3)- A-640. CH3CHF () 4-n-propoxy-phenyl-CH(CH3)- A-641. CH3CHF (R) 4-n-propoxy-phenyl-CH (CH3)- A-642. CH3CHF (S) 4-n-propoxy-phenyl-CH (CH3)- No. R2 R4 A-643. CH3CHF (~) 4-n-butoxy-phenyl-CH(CH3)- A-644. CH3CHF (R) 4-n-butoxyx-phenyl-CH(CH3)- A-645. CH3CHF (S) 4-n-butoxyphenyl-CH(CH3)- A-646. CH3CHF ~ 4-tert-butoxy-phenyl-CH (CH3)- A-647. CH3CHF (R) 4-tert-butoxyx-phenyl-CH (CH3)- A-648. CH3CHF (S) 4-tert-butoxyphenyl-CH (CH3)- A-649. CH3CHF () 4-CH3-phenyl-CH (CH3)- A-650. CH3CHF (R) 4-CH3-phenyl-CH(CH3)- A-651. CH3CHF (S) 4-CH3-phenyl-CH(CH3)- A-652. CH3CHF (~) 4-C2H5-phenyl-CH(CH3)- A-653. CH3CHF (R) 4-C2H5-phenyl-CH (CH3)- A-654. CH3CHF (S) 4-C2H5-phenyl-CH(CH3)- A-655. CH3CHF () 4-n-C3H7-phenyl-CH(CH3)- A-656. CH3CHF (R) 4-n-C3H7-phenyl-CH(CH3)- A-657. CH3CHF (S) 4-n-C3H7-phenyl-CH(CH3)- A-658. CH3CHF (~) 4-iso-C3H7-phenyl-CH(CH3)- A-659. CH3CHF (R) 4-iso-C3H7-phenyl-CH(CH3)- A-660. CH3CHF (S) 4-iso-C3H7-phenyl-CH (CH3)- A-661. CH3CHF () 4-n-C4H9-phenyl-CH (CH3)- A-662. CH3CHF (R) 4-n-C4H9-phenyl-CH (CH3)- A-663. CH3CHF (S) 4-n-C4H9-phenyl-CH (CH3)- A-664. CH3CHF ~) 4-tert-C4H9-phenyl-CH (CH3)- A-665. CH3CHF (R) 4-tert-C4H9-phenyl-CH (CH3)- A-666. CH3CHF (S) 4-tert-C4H9-phenyl-CH (CH3)- A-667. CH3CHF (~) 4-cycl.-C6H11-phenyl-CH(CH3)- A-668. CH3CHF R 4-cycl.-C6H11-phenyl-CH(CH3)- A-669. CH3CHF S 4-cycl.-C6H11-phenyl-CH(CH3)- A-670. CH3CHF () 4-OCF3-phenyl-CH (CH3)- A-671. CH3CHF (R) 4-OCF3-phenyl-CH(CH3)- A-672. CH3CHF (S) 4-OCF3-phenyl-CH(CH3)- A-673. CH3CHF () 4-CF3-phenyl-CH (CH3)- A-674. CH3CHF (R) 4-CF3-phenyl-CH (CH3)- A-675. CH3CHF (S) 4-CF3-phenyi-CH (CH3)- A-676. CH3CHF () 3-F-phenyl-CH(CH3)- A-677. CH3CHF (R) 3-F-phenyl-CH(CH3)- A-678. CH3CHF (S) 3-F-phenyl-CH(CH3)- A-679. CH3CHF () 3-CI-phenyl-CH (CH3)- A-680. CH3CHF (R) 3-CI-phenyl-CH (CH3)- A-681. CH3CHF (S) 3-Cl-phenyl-CH(CH3)- A-682. CH3CHF (~) 3-Br-phenyl-CH(CH3)- A-683. CH3CHF (R) 3-Br-phenyl-CH(CH3)- No. R2 R4 A-684. CH3CHF (S) 3-Br-phenyl-CH (CH3)- A-685. CH3CHF () 3-CF3-phenyl-CH (CH3)- A-686. CH3CHF (R) 3-CF3-phenyl-CH (CH3)- A-687. CH3CHF (S) 3-CF3-phenyl-CH (CH3)- A-688. CH3CHF () 3, 4-F2-phenyl-CH(CH3)- A-689. CH3CHF (R) 3, 4-F2-phenyl-CH(CH3)- A-690. CH3CHF (S) 3, 4-F2-phenyl-CH(CH3)- A-691. CH3CHF (~) 3, 4-Cl2-phenyl-CH(CH3)- A-692. CH3CHF (R) 3, 4-Cl2-phenyl-CH(CH3)- A-693. CH3CHF (S) 3, 4-Cl2-phenyl-CH(CH3)- A-694. CH3CHF () 3, 4-Br2-phenyl-CH(CH3)- A-695. CH3CHF (R) 3, 4-Br2-phenyl-CH(CH3)- A-696. CH3CHF (S) 3, 4-Br2-phenyl-CH(CH3)- A-697. CH3CHF () 4-Difluoromethoxyphenyl-CH (CH3)- A-698. CH3CHF (R) 4-Difluoromethoxyphenyl-CH (CH3)- A-699. CH3CHF (S) 4-Difluoromethoxyphenyl-CH (CH3)- A-700. CH3CHF (~) 4-(1, 1,2, 2-tetrafluoroethox phenyl-CH (CH3)- A-701. CH3CHF (R) 4- (1, 1,2, 2-tetrafluoroethoxy)phenyl-CH(CH3)- A-702. CH3CHF (S) 4- (1, 1,2, 2-tetrafluoroethoxy) phenyl-CH (CH3)- A-703. CH3CHF () (5, 5,7, 7-tetramethylindan-2-yl)-CH(CH3)- A-704. CH3CHF (R) (5, 5,7, 7-tetramethylindan-2-yl)-CH(CH3)- A-705. CH3CHF (S) (5, 5,7, 7-tetramethylindan-2-yl)-CH(CH3)- A-706. CH3CHF () (1,1, 4, 4,-tetramethyl-1, 2,3, 4- tetrahydronaphthalin-6-yl)-CH (CH3)- A-707. CH3CHF (R) (1,1, 4, 4,-tetramethyl-1, 2,3, 4- tetrahydronaphthalin-6-yl)-CH (CH3)- A-708. CH3CHF (S) (1,1, 4, 4,-tetramethyl-1, 2,3, 4- tetrahydronaphthalin-6-yl)-CH (CH3)- A-709. CH3CHF () (1, 1-dimethyl-1, 2,3, 4-tetrahydronaphthalin-6- yl)-CH(CH3)- A-710. CH3CHF (R) (1, 1-dimethyl-1, 2,3, 4-tetrahydronaphthalin-6- l)-CH(CH3)- A-711. CH3CHF (S) (1, 1-dimethyl-1, 2,3, 4-tetrahydronaphthalin-6- l)-CH(CH3)- A-712. CH3CHF (~) (1, 1,4, 4, 7-pentamethyl-1, 2,3, 4- tetrahydronaphthalin-6-yl)-CH (CH3)- A-713. CH3CHF (R) (1,1, 4,4, 7-pentamethyl-1, 2,3, 4- tetrahydronaphthalin-6-yl)-CH (CH3)- A-714. CH3CHF (S) (1,1, 4,4, 7-pentamethyl-1, 2,3, 4- tetrahydronaphthalin-6-yl)-CH(CH3)- A-715. CH3CHF () (1,1, 7-trimethyl-1, 2,3, 4-tetrahydronaphthalin-6- yl)-CH(CH3)- No. R2 R4 A-716. CH3CHF (R) (1,1, 7-trimethyl-1, 2,3, 4-tetrahydronaphthalin- 6-yl)-CH(CH3)- A-717. CH3CHF (S) (1,1, 7-trimethyl-1, 2,3, 4-tetrahydronaphthalin- 6-yl)-CH(CH3)- A-718. CH3CHF (~) (2-methyl-1,3-dioxan-2-yl)-CH(CH3)- A-719. CH3CHF (R) 2-methyl-1, 3-dioxan-2-yl)-CH (CH3)- A-720. CH3CHF (S) 2-methyl-1,3-dioxan-2-yl)-CH(CH3)- A-721. CH3CHF () (2, 5, 5-trimethyl-1,3-dioxan-2-yl)-CH(CH3)- A-722. CH3CHF (R 2,5, 5-trimethyl-1,3-dioxan-2-yl)-CH(CH3)- A-723. CH3CHF (S) 2,5, 5-trimethyl-1,3-dioxan-2-yl)-CH(CH3)- A-724. CH3CHF (~) (2,2-difluorobenzodioxole-5-yl CH (C2H5)- A-725. CH3CHF (R) (2, 2-difluorobenzodioxole-5-yl) CH (C2H5)- A-726. CH3CHF (S) (2, 2-difluorobenzodioxole-5-yl) CH (C2H5)- A-727. CH3CHF C6H5CH2CH2- A-728. CH3CHF 4-F-C6H4CH2CH2- A-729. CH3CHF 4-Cl-C6H4CH2CH2- A-730. CH3CHF 4-Br-C6H4CH2CH2- A-731. CH3CHF 4-CH30-C6H4CH2CH2- A-732. CH3CHF 4-C2H50-C6H4CH2CH2- A-733. CH3CHF 4-n-C3H70-C6H4CH2CH2- A-734. CH3CHF 4-n-C4H90-C6H4CH2CH2- A-735. CH3CHF 4-t-C4H90-C6H4CH2CH2- A-736. CH3CHF 3, 4- (CH30) 2-C6H4CH2CH2- A-737. CH3CHF 4-H3C-C6H4CH2CH2- A-738. CH3CHF 4-H3C-H2C-C6H4CH2CH2- A-739. CH3CHF 4-H3C-H2C-H2C-C6H4CH2CH2- A-740. CH3CHF 4-H3C-H2C-H2C-H2C-C6H4CH2CH2- A-741. CH3CHF 4- (CH3) 3C-C6H4CH2CH2- A-742. CH3CHF 4-F3CO-C6H4CH2CH2- A-743. CH3CHF 4-F3C-C6H4CH2CH2- A-744. CH3CHF 3-F3C-C6H4CH2CH2-

Examples of compounds also are the 6-chloro-[1, 2,4] triazolo- [1, 5-a] pyrimidines of the formula lb, where X is Cl, R1 is CH3 and R3 is H, R2 and R4 together have the meanings given in one row of Table A.

Examples of compounds also are the 6-chloro-[1, 2,4] triazolo- [1, 5-a] pyrimidines of the formula Ic, where X is Cl, R'is OCH3, R3 is H, R2 and R4 together have the meanings given in one row of Table A.

Examples of compounds also are the 6-chloro- [1, 2,4] triazolo- [1, 5-a] pyrimidines of the formula, where X is Cl, R1 is SCH3, R3 is H, R2 and R4 together have the meanings given in one row of Table A.

Examples of compounds also are the 6-chloro- [1, 2,4] triazolo- [1, 5-a] pyrimidines of the formula 1, where X is Cl, R'is SOCH3, R3 is H, R2 and R4 together have the meanings given in one row of Table A.

Examples of compounds also are the 6-chloro- [1, 2,4] triazolo- [1, 5-a] pyrimidines of the formula 1, where X is Cl, R1 is SO2CH3, R3 is H, R2 and R4 together have the meanings given in one row of Table A.

Examples of compounds also are the 6-chloro-[1, 2,4] triazolo- [1, 5-a] pyrimidines of the formula 1, where X is Cl, R1 is CF3, R3 is H, R2 and R4 together have the meanings given in one row of Table A.

Examples of compounds also are the 6-chloro- [1, 2,4] triazolo- [1, 5-a] pyrimidines of the formula 1, where X is Cl, R1 is CN, R 3 is H, R2 and R4 together have the meanings given in one row of Table A.

Examples of compounds also are the 6-chloro- [1, 2,4] triazolo-[1, 5-a] pyrimidines of the formula 1, where X is Cl, R'is OH, R3 is H, R2 and R4 together have the meanings given in one row of Table A.

Examples of compounds also are the 6-chloro-[1, 2,4] triazolo- [1, 5-a] pyrimidines of the formula 1, where X is Cl, R'is OCHF2, R3 is H, R2 and R4 together have the meanings given in one row of Table A.

Examples of compounds also are the 6-chloro-[1, 2,4] triazolo- [1, 5-a] pyrimidines of the formula 1, where X is Cl, R1 is OCF2CHF2, R3 is H, R2 and R4 together have the mean- ings given in one row of Table A.

Examples of compounds also are the 6-chloro-[1, 2,4] triazolo- [1, 5-a] pyrimidines of the formula 1, where X is Cl, R1 is COF3, R3 is H, R2 and R4 together have the meanings given in one row of Table A.

Examples of compounds also are the 6-chloro-[1, 2,4] triazolo- [1, 5-a] pyrimidines of the formula 1, where X is Cl, R'is OCH2C6H5, R3 is H, R2 and R4 together have the mean- ings given in one row of Table A.

Examples of compounds also are the 6-chloro-[1, 2,4] triazolo- [1, 5-a] pyrimidines of the formula 1, where X is Cl, R1 is OCH2CH3, R3 is H, R2 and R4 together have the mean- ings given in one row of Table A.

Examples of compounds also are the 6-chloro- [1, 2,4] triazolo-[1, 5-a] pyrimidines of the formula 1, where X is Cl, R1 is OCH2C#CH, R3 is H, R2 and R4 together have the mean- ings given in one row of Table A.

Examples of compounds also are the 6-chloro- [1, 2,4] triazolo- [1, 5-a] pyrimidines of the formula 1, where X is Cl, R'is OCH (CH3) 2, R3 is H, R2 and R4 together have the mean- ings given in one row of Table A.

Examples of compounds also are the 6-chloro- [1, 2,4] triazolo-[1,5-a]pyrimidines of the formula 1, where X is Cl, R'is O-CH2CH2-O-CH3, R3 is H, R2 and R4 together have the meanings given in one row of Table A.

Examples of compounds also are the 6-chloro-[1, 2,4] triazolo- [1, 5-a] pyrimidines of the formula 1, where X is Cl, R1 is O-CH2CH2-O-CH2CH2-O-CH3, R3 is H, R2 and R4 to- gether have the meanings given in one row of Table A.

Examples of compounds also are the 6-chloro- [1, 2,4] triazolo- [1, 5-a] pyrimidines of the formula 1, where X is Cl, R1 is S-CH2CH2-O-CH3, R3 is H, R2 and R4 together have the meanings given in one row of Table A.

Examples of compounds also are the 6-chloro- [1, 2,4] triazolo- [1, 5-a] pyrimidines of the formula 1, where X is Cl, R1 is S-CH3C(O)-O-CH3, R3 is H, R2 and R4 together have the meanings given in one row of Table A.

Examples of compounds also are the 6-chloro- [1, 2, 4]triazolo-[1,5-a]pyrimidines of the formula 1, where X is Cl, R1 is S-CH2CH2C(O)-O-CH3, R3 is H, R2 and R4 together have the meanings given in one row of Table A.

Examples of compounds also are the 6-chloro- [1, 2,4] triazolo-[1, 5-a] pyrimidines of the formula 1, where X is Cl, R'is S-CH2C (O)-OH, R3 is H, R2 and R4 together have the meanings given in one row of Table A.

The 6-halogeno-[1, 2,4] triazolo- [1, 5-a] pyrimidines of the formula I according to the pre- sent invention can be prepared, for example, similarly to a process described in Phar- mazie, 1971,26, 534 ff or in DD 99 794. The synthesis is shown in Scheme 1. Scheme 1 : R2 x x R3 ruz I \AX, R3 NN\R4 YNAN R4 N, FN N/N N lN U/ \\, N (II) (III) (I)

In Scheme 1, the variables R', R2, R3, R4 and X are as defined above. The reaction of a 6, 7-dihalogeno- [1, 2,4] triazolo- [1, 5-a] pyrimidine of the formula 11 with an amine of the formula III may be carried out in the presence or absence of a solvent. Suitable sol- vents are all solvents which are inert under the reaction conditions, such as aliphatic, cycloaliphatic or aromatic hydrocarbons such as hexane, petrol ether, cyclohexane, benzene, toluene, xylenes, ethers, for example dialkyl ethers, such as diethyl ether, methyl tert-butyl ether, cyclic ethers, such as tetrahydrofuran or dioxane, halogenated hydrocarbons such as dichloromethane or trichloromethane or Ci-C4-alkanols such as methanol, ethanol, n-propanol, iso-propanol, n-butanol or tert-butanol, water or mix- tures of these solvents. It is preferred that the reaction is carried out in the presence of a solvent. If the reaction is carried out in the absence of a solvent, the amine (III) is employed in a large excess, based on 6, 7-dihalogeno- [1, 2,4] triazolo- [1, 5-a] pyrimidin 11.

It is also preferred that the reaction is carried out in the presence of a base. Suitable bases include organic bases, for example tertiary amines, such as trimethylamine, triethylamine, diisopropylethylamine and N-methylpiperidine, pyridine, substituted pyri- dines such as collidine, 2, 3-lutidine, 2, 4-lutidine or 2, 5-lutidine and inorganic bases, for example alkali metal carbonates and alkaline earth metal carbonates such as lithium carbonate, potassium carbonate and sodium carbonate, calcium carbonate and alkali metal hydrogencarbonates such as sodium hydrogen carbonate. An excess of the amine III may serve as base.

The reaction temperature is usually in the range of from 0°C to the boiling of the sol- vent, preferably of from 20 to the 120°C.

The molar ratio of amine III to 6, 7-dihalogeno- [1, 2,4] triazolo- [1, 5-a] pyrimidine 11 is gen- erally at least 0.9 : 1, preferably at least 1: 1. It may be advantageous to employ the amine III in a slight excess, for example of up to 20%, based on the 6, 7-dihalogeno- [1, 2,4] triazolo- [1, 5-a] pyrimidine 11.

In general, the base is employed in at least equimolar amount to a 2-fold molar excess, based on the 6, 7-dihalogeno- [1, 2,4] triazolo- [1, 5-a] pyrimidine 11. It may be advanta-

geous to employ the base in a slight excess, for example up to 30%, based on the 6,7- dihalogeno- [1, 2,4] triazolo- [1, 5-a] pyrimidine 11.

The reaction mixtures are worked up in a customary manner, for example by adding diluted acids, for example mineral acids such as diluted hydrochloric acid, hydrobromic acid and sulfuric acid or aqueous organic acids such as trifluoroacetic acid or acetic acid, aqueous hydrochloric acid being preferred, phase separation and, if appropriate, chromatographic purification, recrystallization, trituration or digestion. The compounds according to the present invention are in general oils, resinous compounds or predomi- nantly crystalline solid materials.

From the preparation, the compounds of formula I may be obtained as isomer mixtures (stereoisomers, enantiomers). If desired, these can be resolved by the methods cus- tomary for this purpose, such as crystallization or chromatography, also on optically active adsorbate, to give the pure isomers.

Some of the amines of the formula III which are employed as starting materials are commercially available. Other may be prepared by processes known in the art, for ex- ample, by conversion of the corresponding alcohols into its tosylates which are then converted to the phthalimido derivatives. The phthalimido derivatives are converted to the desired amines by using hydrazine or any other suitable cleavage agent using con- ventional methods [e. g. J. Am. Soc., Vol. 117, p. 7025 (1995); WO 93/20804] ; by re- duction of the corresponding nitriles [see, Heterocycles, Vol. 35, p. 2 (1993); Synthetic Commun. , Vol. 25, p. 413 (1995); Tetrahedron Lett. , p. 2933 (1995)], or by reductive amination of ketones (see, J. Am. Chem. Soc., Vol. 122, p. 9556 (2000); Org. Lett. , p.

731 (2001), J. Med. Chem. , p. 1566 (1988); by conversion of the appropriate halo- genides and, if appropriate, followed by alkylation. Alternatively, the amine may be car- ried out by addition of Grignard reagents to imines (see R. B. Moffett, Org. Synth. IV, 605 (1963) ). Furthermore, the radical R4 may be introduced by Grignard reaction to nitriles or carboxylic acid anhydrides (see J. Org. Chem. p. 5056 (1992); Tetrahedron Lett. , S. 29933 (1995)). If individual amines III are not disclosed in the cited literature they can be either obtained by routes described above or they can be prepared by de- rivatization of other compounds I I I or by customary modifications of the synthesis routes described above.

The starting materials of the formula 11 may be prepared in two steps, in analogy to the process described in Chem. Pharm. Bull. 1959, Vol. 7, p. 903. The synthesis is shown in Scheme 2.

Scheme 2:

In Scheme 2, the variables Rt, R2 and X are as defined above, X'is halogen, R is alkyl, preferably C1-C6-alkyl, in particular methyl or ethyl and Hal means a halogenating agent. In the first step the 5-aminotriazole of the general formula IV is reacted with the malonic ester of the general formula V. The reaction may be carried out under alkaline conditions, preferably using high boiling tertiary amines as for example tri-n-butylamine.

The 5-aminotriazoles IV are commercially available or can be prepared in analogy to the methods which are well known in the art.

In the second step of Scheme 2 the resulting 6-halogeno-7-hydroxy- [1, 2,4] triazolo [1,5- a] pyrimidine of the general formula VI is treated with a halogenating agent, preferably with a brominating or chlorinating agent. Suitable halogenating agents include inor- ganic acid halides, preferably acid chlorides or acide bromides such as thionyl chloride, thionyl bromide, phosphorus oxychloride, sulfuryl chloride, phosphorus pentachloride or phosphorus tribromide, phosphorus trichloride and mixtures of these. If phosphorus oxychloride is used as a halogenating agent, the reaction is preferably carried out in the presence of a mineral acid, such as polyphosphoric acid and pyridinium salts such as pyridinium bromide or chloride. Preferred halogenating agents are POCI3, PCIS/CI2 or PCI5 and mixtures of these. The reaction can be carried out in the presence or ab- sence of a solvent. The acid halides thionylchloride, phoshorus trichloride or phos- phoryl chloride may simultaneous act as solvent. Suitable solvents are furthermore acetonitrile or dichloromethane. The halogenating agent is generally used in at least equimolar amounts, based on the 6-halogeno-7-hydroxy- [1, 2,4] triazolo [1, 5-a] pyrimidine of the general formula VI. The reaction is suitable carried out at a temperature in the range from 0°C to 150°C, the preferred reaction temperature being from 80°C to 125°C.

Due to their excellent activity, the compounds of the general formula I may be used for controlling animal pests. Animal pests include harmful insects, acaridae and arachnids Accordingly, the invention further provides agriculturally composition for combating animal pests, especially insects, arachnids and/or acaridae which comprises such an amount of at least one compound of the general formula I or at least an agricultural useful salt of I and at least one inert liquid and/or solid agronomically acceptable carrier that it has a pesticidal action and, if desired, at least one surfactant.

Such a composition may contain a single active compound of the general formula I or a mixture of several active compounds I according to the present invention. The compo- sition according to the present invention may comprise an individual isomer or mixtures of isomers.

The 6-halogeno- [1, 2,4] triazolo [1,5-a] pyrimidines and the pestidicidal compositions comprising them are effective agents for controlling animal pests. Animal pests con- trolled by the compounds of formula I include for example: insects from the order of the lepidopterans (Lepidoptera), for example Agrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsia gemmatalis, Argyresthia conjugella, <BR> <BR> Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Cheima- tobia brumata, Choristoneura fumiferana, Choristoneura occidentalis, Cirphis unipuncta, Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandi- osella, Earias insulana, Elasmopalpus lignosellus, Eupoecilia ambiguella, Evetria bou- liana, Feltia subterranea, Galleria mellonella, Grapholitha funebrana, Grapholitha mo- lesta, Heliothis armigera, Heliothis virescens, Heliothis zea, Hellula undalis, Hibernia defoliaria, Hyphantria cunea, Hyponomeuta malinellus, Keiferia lycopersicella, Lamb- dina fiscellaria, Laphygma exigua, Leucoptera coffeella, Leucoptera scitella, Lithocol- letis blancardella, Lobesia botrana, Loxostege sticticalis, Lymantria dispar, Lymantria monacha, Lyonetia clerkella, Malacosoma neustria, Mamestra brassicae, Orgyia pseu- dotsugata, Ostrinia nubilalis, Panolis flammea, Pectinophora gossypiella, Peridroma saucia, Phalera bucephala, Phthorimaea operculella, Phyllocnistis citrella, Pieris bras- sicae, Plathypena scabra, P/ufe//a xylostella, Pseudoplusia includens, Rhyacionia frus- trana, Scrobipalpula absoluta, Sitotroga cerealella, Sparganothis pilleriana, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, Thaumatopoea pityocampa, Tortrix viridana, Trichoplusia ni and Zeiraphera canadensis ; beetles (Coleoptera), for example Agrilus sinuatus, Agriotes lineatus, Agriotes obscu- rus, Amphimallus solstitialis, Anisandrus dispar, Anthonomus grandis, Anthonomus pomorum, Atomaria linearis, Blastophagus piniperda, Blitophaga undata, Bruchus rufi- manus, Bruchus pisorum, Bruchus lentis, Byctiscus betulae, Cassida nebulosa, Cero- toma trifurcata, Ceuthorrhynchus assimilis, Ceuthorrhynchus napi, Chaetocnema tibi- alis, Conoderus vespertinus, Crioceris asparagi, Diabrotica longicomis, Diabrotica 12- punctata, Diabrotica virgifera, Epilachna varivestis, Epitrix hirtipennis, Eutinobothrus brasiliensis, Hylobius abietis, Hypera brunneipennis, Hypera postica, Ips typographus, Lema bilineata, Lema melanopus, Leptinotarsa decemlineata, Limonius califomicus, Lissorhoptrus oryzophilus, Melanotus communis, Meligethes aeneus, Melolontha hip- pocastani, Melolontha melolontha, Oulema oryzae, Ortiorrhynchus sulcatus, Otiorrhyn- chus ovatus, Phaedon cochleariae, Phyllotreta chrysocephala, Phyllophaga sp. , Phyl- lopertha horticola, Phyllotreta nemorum, Phyllotreta striolata, Popillia japonica, Sitona lineatus and Sitophilus granaria ;

dipterans (Diptera), for example Aedes aegypti, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Ceratitis capitata, Chrysomya bezziana, Chrysomya homi- nivorax, Chrysomya macellaria, Contarinia sorghicola, Cordylobia anthropophaga, Culex pipiens, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Fannia canicu- laris, Gasterophilus intestinalis, Glossina morsitans, Haematobia irritans, Haplodiplosis equestris, Hylemyia platura, Hypoderma lineata, Liriomyza sativae, Liriomyza trifolii, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mayetiola destruc- tor, Musca domestica, Muscina stabulans, Oestrus ovis, Oscinella frit, Pegomya hyso- cyami, Phorbia antiqua, Phorbia brassicae, Phorbia coarctata, Rhagoletis cerasi, Rhagoletis pomonella, Tabanus bovinus, Tipula oleracea and Tipula paludosa ; thrips (Thysanoptera), e. g. Dichromothrips corbetti, Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi and Thrips tabaci ; hymenopterans (Hymenoptera), e. g. Athalia rosae, Atta cephalotes, Atta sexdens, Atta texana, Hoplocampa minuta, Hoplocampa testudinea, Monomorium pharaonis, So- lenopsis geminata and Solenopsis invicta ; heteropterans (Heteroptera), e. g. Acrostemum hilare, Blissus leucopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus intermedius, Eurygaster integriceps, Euschistus impictiventris, Leptoglossus phyllopus, Lygus lineolaris, Lygus pratensis, Nezara viridula, Piesma quadrata, Solubea insularis and Thyanta perditor, homopterans (Homoptera), e. g. Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphis fabae, Aphis forbesi, Aphis pomi, Aphis gossypii, Aphis grossulariae, Aphis schneideri, Aphis spiraecola, Aphis sambuci, Acyrthosiphon pisum, Aulacorthum solani, Bemisia argentifolii, Brachycaudus cardui, Brachycaudus helichrysi, Brachy- caudus persicae, Brachycaudus prunicola, Brevicoryne brassicae, Capitophorus horni, Cerosipha gossypii, Chaetosiphon fragaefolii, Cryptomyzus ribis, Dreyfusia norman- nianae, Dreyfusia piceae, Dysaphis radicola, Dysaulacorthum pseudosolani, Dysaphis plantaginea, Dysaphis pyri, Empoasca fabae, Hyalopterus pruni, Hyperomyzus lactu- cae, Macrosiphum avenae, Macrosiphum euphorbiae, Macrosiphon rosae, Megoura viciae, Melanaphis pyrarius, Metopolophium dirhodum, Myzodes persicae, Myzus as- calonicus, Myzus cerasi, Myzus persicae, Myzus varians, Nasonovia ribis-nigri, Nila- parvata lugens, Pemphigus bursarius, Perkinsiella saccharicida, Phorodon humuli, Psylla mali, Psylla piri, Rhopalomyzus ascalonicus, Rhopalosiphum maidis, Rhopalosi- phum padi, Rhopalosiphum insertum, Sappaphis mala, Sappaphis mali, Schizaphis graminum, Schizoneura lanuginosa, Sitobion avenae, Sogatella furcifera Trialeurodes vaporariorum, Toxoptera aurantiiand, and Viteus vitifolii ; termites (Isoptera), e. g. Calotermes flavicollis, Leucotermes flavipes, Reticulitermes flavipes, Reticulitermes lucifugus und Termes natalensis ;

orthopterans (Orthoptera), e. g. Acheta domestica, Blatta orientalis, Blattella germanica, Forficula auricularia, Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplus bivittatus, Melanoplus femur-rubrum, Melanoplus mexicanus, Melanoplus sanguinipes, Melano- plus spretus, Nomadacris septemfasciata, Periplaneta americana, Schistocerca ameri- cana, Schistocerca peregrina, Stauronotus maroccanus and Tachycines asynamorus ; Arachnoidea, such as arachnids (Acarina), e. g. of the families Argasidae, Ixodidae and Sarcoptidae, such as Amblyomma americanum, Amblyomma variegatum, Argas persi- cus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Dermacentor silvarum, Hyalomma truncatum, Ixodes ricinus, Ixodes rubicundus, Omithodorus mou- bata, Otobius megnini, Dermanyssus gallinae, Psoroptes ovis, Rhipicephalus appendi- culatus, Rhipicephalus evertsi, Sarcoptes scabiei, and Eriophyidae spp. such as Aculus schlechtendali, Phyllocoptrata oleivora and Eriophyes sheldoni ; Tarsonemidae spp. such as Phytonemus pallidus and Polyphagotarsonemus latus ; Tenuipalpidae spp. such as Brevipalpus phoenicis ; Tetranychidae spp. such as Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus pacificus, Tetranychus telarius and Tetranychus urticae, Panonychus ulmi, Panonychus citri, and oligonychus pratensis ; Siphonatera, e. g. Xenopsylla cheopsis, Ceratophyllus spp.

The compounds of the formula I are preferably used for controlling pests of the orders Lepidoptera, Coleoptera, Homoptera and Acarina.

The compounds of formula (I) or the pesticidal compositions comprising them may be used to protect growing plants and crops from attack or infestation by animal pests, especially insects, acaridae or arachnids by contacting the plant/crop with a pesticidally effective amount of compounds of formula (I). The term"crop"refers both to growing and harvested crops.

The animal pest, especially the insect, acaridae, arachnid, plant and/or soil or water in which the plant is growing can be contacted with the present compound (s) I or compo- sition (s) containing them by any application method known in the art. As such,"contact- ing"includes both direct contact (applying the compounds/compositions directly on the animal pest, especially the insect, acaridae and/or arachnid, and/or plant-typically to the foliage, stem or roots of the plant) and indirect contact (applying the com- pounds/compositions to the locus of the animal pest, especially the insect, acaridae, and/or arachnid, and/or plant).

Moreover, animal pests, especially insects, acaridae or arachnids may be controlled by contacting the target pest, its food supply or its locus with a pesticidally effective amount of compounds of formula (I). As such, the application may be carried out before or after the infection of the locus, growing crops, or harvested crops by the pest.

"Locus"means a habitat, breeding ground, plant, seed, soil, area, material or environ- ment in which a pest or parasite is growing or may grow.

Effective amounts suitable for use in the method of invention may vary depending upon the particular formula I compound, target pest, method of application, application tim- ing, weather conditions, animal pest habitat, especially insect, arachnid or acarid habi- tat, or the like. In general, for use in treating crop plants, the rate of application of the compounds I and/or compositions according to this invention may be in the range of about 0.1 g to about 4000 g per hectare, desirably from about 25 g to about 600 g per hectare, more desirably from about 50 g to about 500 g per hectare. For use in treating seeds, the typical rate of application is of from about 1 g to about 500 g per kilogram of seeds, desirably from about 2 g to about 300 g per kilogram of seeds, more desirably from about 10 g to about 200 g per kilogram of seeds. Customary application rates in the protection of materials are, for example, from about 0.001 g to about 2000 g, de- sirably from about 0.005 g to about 1000 g, of active compound per cubic meter of treated material.

The compounds I or the pesticidal compositions comprising them can be used, for ex- ample in the form of solutions, emulsions, microemulsions, suspensions, flowable con- centrates, dusts, powders, pastes and granules. The use form depends on the particu- lar purpose; in any case, it should guarantee a fine and uniform distribution of the com- pound according to the invention.

The pesticidal composition for combating animal pests, especially insects, acaridae and/or arachnids contains such an amount of at least one compound of the general formula I or an agricultural useful salt of I and auxiliaries which are usually used in formulating pesticidal composition.

The formulations are prepared in a known manner, e. g. by extending the active ingre- dient with solvents and/or carriers, if desired using emulsifiers and dispersants, it also being possible to use other organic solvents as auxiliary solvents if water is used as the diluent. Auxiliaries which are suitable are essentially: solvents such as aromatics (e. g. xylene), chlorinated aromatics (e. g. chlorobenzenes), paraffins (e. g. mineral oil frac- tions), alcohols (e. g. methanol, butanol), ketones (e. g. cyclohexanone), amines (e. g. ethanolamine, dimethylformamide) and water; carriers such as ground natural minerals (e. g. kaolins, clays, talc, chalk) and ground synthetic minerals (e. g. highly-disperse silica, silicates) ; emulsifiers such as non-ionic and anionic emulsifiers (e. g. poly- oxyethylene fatty alcohol ethers, alkylsulfonates and arylsulfonates) and dispersants such as lignin-sulfite waste liquors and methylcellulose.

Suitable surfactants are alkali metal, alkaline earth metal and ammonium salts of ligno- sulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkylsulfonates, fatty alcohol sulfates and fatty acids and their alkali metal and alkaline earth metal salts, salts of sulfate fatty alcohol

glycol ether, condensates of sulfonate naphthalene and naphthalene derivatives with formaldehyde, condensates of naphthalene or of napthalenesulfonic acid with phenol or formaldehyde, polyoxyethylene octylphenyl ether, ethoxylated isooctylphenol, octyl- phenol, nonylphenol, alkylphenol polyglycol ethers, tributylphenyl polyglycol ethers, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol/ethylene oxide conden- sates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropyl- ene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignin-sulfite waste liquors and methylcellulose.

Substances which are suitable for the preparation of directly sprayable solutions, emul- sions, pastes or oil dispersions are mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e. g. benzene, toluene, xylene, par- affin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanbl, butanol, chloroform, carbon tetrachloride, cyclohexanol, cyclohexa- none, chlorobenzene, isophorone, strongly polar solvents, e. g. dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone and water.

Powders, materials for scattering and dusts can be prepared by mixing or concomi- tantly grinding the active substances with a solid carrier.

Granules, e. g. coated granules, compacted granules, impregnated granules and ho- mogeneous granules, can be prepared by binding the active ingredients to solid carri- ers. Examples of solid carriers are mineral earths, such as silicas, silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materi- als, fertilizers, e. g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders and other solid carriers.

Such formulations or compositions of the present invention include a formula I com- pound of this invention (or combinations thereof) admixed with one or more agronomi- cally acceptable inert, solid or liquid carriers. Those compositions contain a pesticidally effective amount of said compound or compounds, which amount may vary depending upon the particular compound, target pest, and method of use.

In general, the formulations comprise of from 0.01 to 95% by weight, preferably from 0.1 to 90% by weight, of the active ingredient. The active ingredients are employed in a purity of from 90% to 100%, preferably 95% to 100% (according to NMR spectrum).

The following are exemplary formulations: I. 5 parts by weight of a compound according to the invention are mixed intimately with 95 parts by weight of finely divided kaolin. This gives a dust which comprises

5% by weight of the active ingredient.

II. 30 parts by weight of a compound according to the invention are mixed intimately with a mixture of 92 parts by weight of pulverulent silica gel and 8 parts by weight of paraffin oil which had been sprayed onto the surface of this silica gel.

This gives a formulation of the active ingredient with good adhesion properties (comprises 23% by weight of active ingredient).

III. 10 parts by weight of a compound according to the invention are dissolved in a mixture composed of 90 parts by weight of xylene, 6 parts by weight of the ad- duct of 8 to 10 mol of ethylene oxide and 1 mol of oleic acid N- monoethanolamide, 2 parts by weight of calcium dodecylbenzenesulfonate and 2 parts by weight of the adduct of 40 mol of ethylene oxide and 1 mol of castor oil (comprises 9% by weight of active ingredient).

IV. 20 parts by weight of a compound according to the invention are dissolved in a mixture composed of 60 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 5 parts by weight of the adduct of 7 mol of ethylene oxide and 1 mol of isooctylphenol and 5 parts by weight of the adduct of 40 mol of ethylene oxide and 1 mol of castor oil (comprises 16% by weight of active ingredient).

V. 80 parts by weight of a compound according to the invention are mixed thor- oughly with 3 parts by weight of sodium diisobutylnaphthalene-alpha-sulfonate, 10 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 7 parts by weight of pulverulent silica gel, and the mixture is ground in a hammer mill (comprises 80% by weight of active ingredient).

VI. 90 parts by weight of a compound according to the invention are mixed with 10 parts by weight of N-methyl-a-pyrrolidone, which gives a solution which is suit- able for use in the form of microdrops (comprises 90% by weight of active ingre- dient).

VIl. 20 parts by weight of a compound according to the invention are dissolved in a mixture composed of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 mol of ethylene oxide and 1 mol of isooctylphenol and 10 parts by weight of the adduct of 40 mol of ethylene ox- ide and 1 mol of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which com- prises 0.02% by weight of the active ingredient.

VIII. 20 parts by weight of a compound according to the invention are mixed thor- oughly with 3 parts by weight of sodium diisobutylnaphthalene-a-sulfonate, 17 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liq- uor and 60 parts by weight of pulverulent silica gel, and the mixture is ground in

a hammer mill. Finely distributing the mixture in 20,000 parts by weight of water gives a spray mixture which comprises 0. 1 % by weight of the active ingredient.

The active ingredients can be used as such, in the form of their formulations or the use forms prepared therefrom, e. g. in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, materials for spreading, or granules, by means of spraying, atomizing, dusting, scattering or pouring.

The use forms depend entirely on the intended purposes; in any case, this is intended to guarantee the finest possible distribution of the active ingredients according to the invention.

Aqueous use forms can be prepared from emulsion concentrates, pastes or wettable powders (sprayable powders, oil dispersions) by adding water. To prepare emulsions, pastes or oil dispersions, the substances as such or dissolved in an oil or solvent, can be homogenized in water by means of wetter, tackifier, dispersant or emulsifier. Alter- naively, it is possible to prepare concentrates composed of active substance, wetter, tackifier, dispersant or emulsifier and, if appropriate, solvent or oil, and such concen- trates are suitable for dilution with water.

The active ingredient concentrations in the ready-to-use products can be varied within substantial ranges. In general, they are from 0.0001 to 10%, preferably from 0.01 to 1%.

The active ingredients may also be used successfully in the ultra-low-volume process (ULV), it being possible to apply formulations comprising over 95% by weight of active ingredient, or even the active ingredient without additives.

Compositions to be used according to this invention may also contain other active ingredients, for example other pesticides, insecticides, herbicides, fungicides, other pesticides, or bactericides, fertilizers such as ammonium nitrate, urea, potash, and superphosphate, phytotoxicants and plant growth regulators, safeners and nematicides. These additional ingredients may be used sequentially or in combination with the above-described compositions, if appropriate also added only immediately prior to use (tank mix). For example, the plant (s) may be sprayed with a composition of this invention either before or after being treated with other active ingredients.

These agents can be admixed with the agents used according to the invention in a weight ratio of 1: 10 to 10: 1. Mixing the compounds I or the compositions comprising them in the use form as pesticides with other pesticides frequently results in a broader pesticidal spectrum of action.

The following list of pesticides together with which the compounds of formula I can be used, is intended to illustrate the possible combinations, but not to impose any

limitation: Organophosphates : Acephate, Azinphos-methyl, Chlorpyrifos, Chlorfenvinphos, Diazi- non, Dichlorvos, Dicrotophos, Dimethoate, Disulfoton, Ethion, Fenitrothion, Fenthion, Isoxathion, Malathion, Methamidophos, Methidathion, Methyl-Parathion, Mevinphos, Monocrotophos, Oxydemeton-methyl, Paraoxon, Parathion, Phenthoate, Phosalone, Phosmet, Phosphamidon, Phorate, Phoxim, Pirimiphos-methyl, Profenofos, Prothiofos, Sulprophos, Triazophos, Trichlorfon ; Carbamates: Alanycarb, Benfuracarb, Carbaryl, Carbosulfan, Fenoxycarb, Furathio- carb, Indoxacarb, Methiocarb, Methomyl, Oxamyl, Pirimicarb, Propoxur, Thiodicarb, Triazamate; Pyrethroids: Bifenthrin, Cyfluthrin, Cypermethrin, Deltamethrin, Esfenvalerate, Ethofen- prox, Fenpropathrin, Fenvalerate, Cyhalothrin, Lambda-Cyhalothrin, Permethrin, Si- lafluofen, Tau-Fluvalinate, Tefluthrin, Tralomethrin, Zeta-Cypermethrin ; Arthropod growth regulators : a) chitin synthesis inhibitors: benzoylureas : Chlorflua- zuron, Diflubenzuron, Flucycloxuron, Flufenoxuron, Hexaflumuron, Lufenuron, Novalu- ron, Teflubenzuron, Triflumuron ; Buprofezin, Diofenolan, Hexythiazox, Etoxazole, Clofentazine ; b) ecdysone antagonists: Halofenozide, Methoxyfenozide, Tebufenozide; c) juvenoids: Pyriproxyfen, Methoprene, Fenoxycarb; d) lipid biosynthesis inhibitors: Spirodiclofen ; Various: Abamectin, Acequinocyl, Amitraz, Azadirachtin, Bifenazate, Cartap, Chlor- fenapyr, Chlordimeform, Cyromazine, Diafenthiuron, Dinetofuran, Diofenolan, Ema- mectin, Endosulfan, Ethiprole, Fenazaquin, Fipronil, Formetanate, Formetanate hydro- chloride, Hydramethyinon, Imidacloprid, Indoxacarb, Pyridaben, Pymetrozine, Spino- sad, Sulfur, Tebufenpyrad, Thiamethoxam, and Thiocyclam.

The present invention is now illustrated in further detail by the following examples.

1. Synthesis Examples Example 1: (cis-4-tert-butyl-cyclohexyl)- [6-chloro-5-ethyl- [1, 2,4] triazolo [1,5- a] pyrimidin-7-yl]-amine

0.280 g (2.76 mmol) Triethylamine, a spatula tip of tetrabutylammonium iodide and 0.393 g (2.53 mmol) of cis-4-tert-butylcyclohexylamine were added successively to a solution of 0.500 g (2.3 mmol) of 5-ethyl-6, 7-dichloro- [1, 2,4] triazolo [1,5-a] pyrimidine in 10 ml of toluene under stirring. The reaction mixture was heated at reflux for 5 hours and then stirred for another 12 hours at room temperature. The solvent was evaporated under reduced pressure and dichloromethane was added to the resulting residue. The resulting reaction mixture was washed with 2N hydrochloric acid and water. The or- ganic phase was separated, dried and the solvent was evaporated under reduced pressure. Treatment of the resulting residue with hexane yielded 0.420 g (1.2 mmol, 52% of theory) of the title compound having a melting point of 120-122°C.

1 H-NMR (CDC13) 8 : 8.25 (s, 1H), 6.20 (m, 1H), 5.20 (m, 1H), 3.00 (q, 2H), 2.05 (d, 2H), 1.85 (s, 1H), 1.70 (t, 4H), 1.35 (t, 3H), 1.30-1. 10 (m, 2H), 0.90 (s, 9H).

Example 2: (cis-4-tert-butyl-cyclohexyl)- [6-chloro-5- (1-fluoro-ethyl)- [1, 2,4] triazolo [1, 5- a] pyrimidin-7-yl]-amine 0.220 g (2.2 mmol) Triethylamine, a spatula tip of tetrabutylammonium iodide and 0.340 g (2.2 mmol) of cis-4-tert-butylcyclohexylamine were added successively to a solution of 0.470 g (2.0 mmol) of 5- (1-fluoroethyl)-6, 7-dichloro- [1, 2,4] triazolo [1,5- a] pyrimidine in 15 ml of toluene under stirring. The reaction mixture was heated at re- flux for 5 hours and then stirred for another 12 hours at room temperature. The solvent was evaporated under reduced pressure and dichloromethane was added to the result- ing residue. The resulting reaction mixture was washed with 2N hydrochloric acid and water. The organic phase was separated, dried and the solvent was evaporated under reduced pressure. Treatment of the resulting residue with hexane yielded 0.540 g (1.5 mmol, 76% of theory) of the title compound having a melting point of 138-139°C.

1H-NMR (CDCI3) S : 8.35 (s, 1H), 6.35 (bd, 1H), 6.00 (dq, 1H), 5.25 (bm, 1H), 2.00 (bd, 2H), 1.75 (dd, 3H), 1.70 (m, 3H), 1.30-1. 10 (m, 4H), 0.90 (s, 9H).

Example 105: (6-chloro-5-ethyl- [1, 2,4] triazolo [1,5-a] pyrimidin-7-yi)- [ (2- (4- trifluoromethoxyphenyl)-ethyl]-amine

0.510 g (5.1 mmol) Triethylamine, a spatula tip of tetrabutylammonium iodide and 1.04 g (5. 1 mmol) of 2- (4-trifluoromethoxyphenyl)-ethylamine were added successively to a solution of 1.0 g (4.6 mmol) of 5-ethyl-6, 7-dichloro- [1, 2,4] triazolo- [1, 5-a] pyrimidine in 10 mi of toluene under stirring. The reaction mixture was heated at reflux for 5 hours and then stirred for another 12 hours at room temperature. The solvent was evaporated under reduced pressure and dichloromethane was added to the resulting residue. The resulting reaction mixture was washed with 2N hydrochloric acid and water. The or- ganic phase was separated, dried and the solvent was evaporated under reduced pressure. Treatment of the resulting residue with hexane yielded 1.60 g (5.0 mmol, 99% of theory) of the title compound having a melting point of 186-187 °C.

'H-NMR (CDCI3) 6 : 8.25 (s, 1 H), 7.25 (d, 2H), 7.20 (d, 2H), 6.00 (bm, 1 H), 4.45 (q, 2H), 3.10 (t, 2H), 3.00 (q, 2H), 1.35 (t, 3H).

Example 114 : (S)- (6-chloro-5-methyl- [1, 2,4] triazolo [1,5-a] pyrimidin-7-yi)- [l- (4-fluoro- phenyl)-ethyl]-amine 0.300 g (3.0 mmol) Triethylamine, a spatula tip of tetrabutylammonium iodide and 0.514 g (3.7 mmol) of (S)-1- (4-fluorophenyl)-ethylamine were added successively to a solution of 0.500 g (2.5 mmol) of 5-methyl-6, 7-dichloro- [1, 2,4] triazolo [1, 5-a] pyrimidine in 10 ml of toluene under stirring. The reaction mixture was heated at reflux for 5 hours and then stirred for another 12 hours at room temperature. The solvent was evaporated under reduced pressure and dichloromethane was added to the resulting residue. The resulting reaction mixture was washed with 2N hydrochloric acid and with water. The organic phase was separated, dried and the solvent was evaporated under reduced pressure. Treatment of the resulting residue with hexane yielded 0.520 g (1,7 mmol, 68% of theory) of the title compound having a melting point of 103-104°C.

'H-NMR (CDC13) 8 : 8.25 (s, 1 H), 7.30 (dd, 2H), 7.00 (t, 2H), 6.25 (m, 1 H), 6.05 (bd, 1 H), 2.60 (s, 3H), 1.75 (d, 3H).; The compounds of Inventive Examples 1 to 197 were listed in the following Table 1.

The synthesis of compounds according to the invention not described was in an analo- gous manner as described above:

Table 1 : Example R1 R2 R4 +) m.p. [°C] No. 1. H C2H5 cis-4-tert-butylcyclohexyl- 120-122 2. H CH3CHF cis-4-tert-butylcyclohexyl-138-139 3. H CH3 4-methylcyclohexyl-134-136 4. H CH3 4-tert-butylcyclohexyl-165-167 5. H CH3 4- (cyclohexyl-C (CH3) 2)-cyclohexyl- 188-190 6. H CH3 4-((CH3)2CH)-cyclohexyl- 109-112 7. H CH3 4-tert-butylcyclohexyl-130-134 8. H CH3 cis-4-sec.-butylcyclohexyl-88-90 9. H CH3 trans-4-sec.-butylcyclohexyl-149-150 10. H CH3 trans-4-tert-butylcyclohexyl-138-140 11. H CH3 cis-(CH3)3C-CH2-C(CH3)2-cyclohexyl- 162-165 12. H CH3 trans-(CH3)3C-CH2-C(CH3)2-cyclohexyl- 164-166 13. H C2H5 4-tert-butylcyclohexyl-118-142 14. H C2H5 cis-4-sec.-butylcyclohexyl-91-93 15. H C2H5 trans-4-tert-butylcyclohexyl-183-184 16. H C2H5 trans-4-sec.-butylcyclohexyl- 164-165 17. H C2H5 trans-(CH3)3C-CH2-C(CH3)2-cyclohexyl- 177-179 18. H C2H5 4-methylcyclohexyl- 150-152 19. H C2H5 4- (cyclohexyl-C (CH3) 2)-cyclohexyl- 205-209 20. H C2H5 4-((CH3)2CH)-cyclohexyl- 140-144 21. H3CS02 C2H5 cis-4-tert-butylcyclohexyl-resinous 22. H3CSO C2H5 cis-4-tert-butylcyclohexyl-89-97 23. SCH3 C2H5 cis-4-tert-butylcyclohexyl-125-128 24. H CF3 4-tert-butylcyclohexyl-155-157 25. H CF3 4-methylcyclohexyl- 171-173 26. H CF3 4- (cyclohexyl-C (CH3) 2)-cyclohexyl- 191-193 27. H CF3 4-((CH3)2CH)-cyclohexyl- 160-161 28. H CH3CHCl cis-4-tert-butylcyclohexyl- 153-155 Example R1 R2 R4 +) m.p. [°C] No. 29. H CH3 (R)-indan-1-yl 108-111 30. H CH3 (S)-indan-1-yl 115-119 31. H C2H5 (R)-indan-1-yl 95-97 32. H C2H5 (S)-indan-1-yl. 96-98 33. H CH3 (R)-1, 2,3, 4-tetrahydronaphthalen-1-yl 110-113 34. H CH3 (S)-1, 2,3, 4-tetrahydronaphthalen-1-yl 121-124 35. H C2H5 (R)-1, 2,3, 4-tetrahydronaphthalen-1-yl 80-81 36. H C2H5 (S)-1,2,3,4-tetrahydronaphthalen-1-yl 82-84 37. H CH3 4-F-C6H4-resinous 38. H CH3 C6H5-200-201 39. H CH3 4-Cl-C6H4 138-141 40. H CH3 4-(C6H5)-C6H4- 139-141 41. H CH3 4-phenoxyphenyl 171-172 42. H CH3 4-((CH3)3C)-C6H4- 160-163 43. H C2H5 4-((CH3)3C)-C6H4- 182-185 44. H C2H5 phenyl 201-202 45. H C2H5 4-F-C6H4-213-214 46. H C2H5 4-CI-C6H4-200-201 47. H C2H5 4- (C6H5)-C6H4- 159-162 48. H C2H5 4-phenoxyphenyl 183-185 49. H CF3 4-(C6H5)-C6H4- 209-210 50. H CF3 C6H5-211-213 51. H CF3 4-F-C6H4-193-196 52. H CF3 4-Cl-C6H4- 177-179 53. H CF3 4-phenoxyphenyl 190-193 54. H CH3CHF 4-tert-butylphenyl 183-186 55. H CH3 benzyl 129-130 56. H CH3 4-trifluoromethylbenzyl 128-132 57. H CH3 4-tert-butylbenzyl 164-168 58. H CH3 4-tert-butoxybenzyl 102-105 59. H CH3 3, 4-Cl2C6H3-CH2- 195-200 60. H CH3 4-chlorobenzyl 171-175 61. H CH3 4- (4-methoxyphenoxy) phenyl-CH2-132-136 62. H CH3 4- (4-tert-butylphenoxy) phenyI-CH2-resinous 63. H CH3 4-(4-bromophenoxy)phenyl-CH2- 150-152 64. H CH3 4-(4-ethylphenoxy)phenyl-CH2- 160-162 65. H CH3 4- (4-methylphenoxy) phenyl-CH2 156-158 66. H CH3 4-(4-chlorophenoxy)phenyl-CH2- 146-148 67. H CH3 4-(2-ethylphenoxy)phenyl-CH2- 157-159 68. H CH3 4-(3-ethylphenoxy)phenyl-CH2- resinous Example R1 R2 R4 +) m.p. [°C] No. 69. H CH3 4- (2-bromophenoxy) phenyl-CH2-162-164 70. H CH3 4-(3-chlorophenoxy)phenyl-CH2- 167-168 71. H CH3 4-(2-methylphenoxy)phenyl-CH2- 155-161 72. H CH3 4- (2-tert-butylphenoxy) phenyl-CH2-152-155 73. H CH3 4-(2-chlorophenoxy)phenyl-CH2- 165-167 74. H CH3 4- (3-fluorophenoxy) phenyl-CH2-167-174 75. H CH3 4- (3-bromophenoxy) phenyl-CH2 158-160 76. H CH3 4- (4-isopropylphenoxy) phenyl-CH2-160-163 77. H CH3 4-(3-fluoro-4-chlorophenoxy)phenyl-CH2- 106-108 78. H CH3 4-(3-chloro-4-bromophenoxy)phenyl-CH2- 135-138 79. H CH3 4-(3-chloro-4-methylphenoxy)phenyl-CH2- 138-140 80. H CH3 4-(3,4-difluorophenoxy)phenyl-CH2- 121-124 81. H CH3 4-(3-methyl-4-chlorophenoxy)phenyl-CH2- 145-148 82. H CH3 4-(3,4-dimethylphenoxy)phenyl-CH2- 157-159 83. H CH3 4-(3-chloro-4-fluorophenoxy)phenyl-CH2- 122-125 84. H CH3 4-(3,4-dichlorophenoxy)phenyl-CH2- resinous 85. H CH3 4-(3-methyl-4-bromophenoxy)phenyl-CH2- 158-160 86. H C2H5 4- (4-ethylphenoxy) phenyl-CH2-resinous 87. H C2H5 benzyl 115-116 88. H C2H5 3, 4-Cl2C6H3-CH2- 181-184 89. H C2H5 4-F3C-C6H4-CH2-169-171 90. H C2H5 4-tert-butylphenyl-CH2-111-113 91. H C2H5 4-(4-tert-butoxy)-C6H4-CH2- 80-85 92. H C2H5 4-Cl-C6H4-CH2- 142-146 93. H C2H5 4-(4-methoxyphenoxy)phenyl-CH2- 100-106 94. H CF3 C6H5-CH2-154-156 95. H CF3 4-tert-butylphenyl-CH2-109-111 96. H CH3 C6H5-CH2CH2-161-163 97. H CH3 4-CI-C6H4-CH2CH2-165-167 98. H CH3 4-F-C6H4-CH2CH2-180-182 99. H CH3 4-F3C-C6H4-CH2CH2-185-187 100. H CH3 3,4-(CH3O)2C6H3-CH2CH2- 161-163 101. H CH3 4-tert-butylphenyl-CH2CH2-150-151 102. H CH3 4-F3C-O-C6H4CH2CH2-182-184 103. H C2H5 4-F-C6H4-CH2CH2-162-165 104. H C2H5 4-F3C-C6H4-CH2CH2-179-183 105. H C2H5 4-trifluoromethoxy-C6H4CH2CH2-186-187 106. H C2H5 C6H5-CH2CH2-158-160 107. H C2H5 4-CI-C6H4-CH2CH2-170-172 108. H C2H5 3,4-(CH3O)2C6H3-CH2CH2- 143-145 Example R1 R2 R4 +) m.p. [°C] No. 109. H C2H5 4-tert-butylphenyl-CH2CH2-172-174 110. H CF3 4-tert-butylphenyl-CH2CH2-176-178 111. H CF3 C6H5-CH2CH2-161-163 112. H CF3 3,4-(CH3O)2C3H3-CH2CH2- 183-186 113. H CH3CHF 4-trifluoromethoxy-C6H4-CH2CH2-167-168 114. H CH3 (S)-4-F-C6H4-CH(CH3)- 103-104 115. H CH3 4-Cl-C6H4-CH(CH3)- 93-95 116. H CH3 4-F-C6H4-CH (CH3)- 75-77 117. H CH3 (R)-C6H5-CH (CH3)-95-98 118. H C2H5 4-Cl-C6H4-CH(CH3)- resinous 119. H CH3 4-Br-C6H4-CH (CH3)- 79-82 120. H CH3 (S)-4-Cl-C6H4-CH(CH3)- 122-123 121. H CH3 (S)-4-CH30-C6H4-CH (CH3)- 107-108 122. H CH3 (S)-4-CH3-C6H4-CH(CH3)- 164-166 123. H CH3 3, 4-Cl2-C6H3-CH(CH3)- 103-105 124. H CH3 3-CIC6H4-CH (CH3)- 105-108 125. H CH3 4-F3C-C6H4-CH (CH3)- 85-88 126. H CH3 (S)-C6H5-CH(CH3)- resinous 127. H CH3 4-(4-CH3-C6H4-O)-C6H4-CH(CH3)- 136-140 128. H CH3 (R)-4-CH3-C6H4-CH (CH3)- 156-159 129. H CH3 (R)-4-CI-C6H4-CH (CH3)-117-122 130. H CH3 (R)-4-Br-C6H4-CH(CH3)- 116-119 131. H CH3 (S)-4-Br-C6H4-CH (CH3)- 114-130 132. H CH3 (R)-4-F-C6H4-CH (CH3)- 105-107 133. H CH3 (R)-3-CH30-C6H4-CH (CH3)- 86-110 134. H CH3 (S)-3-CH30-C6H4-CH (CH3)- 83-100 135. H CH3 4-CF30-C6H4-CH (CH3)- 98-101 136. H CH3 (R)-4-CH30-C6H4-CH (CH3)- 99-136 137. H CH3 (R)-3-(C6H5-CH2-O)-C6H4-CH(CH3)- resinous 138. H CH3 (S)-4-benzyloxy-C6H4-CH (CH3)-resinous 139. H CH3 (R)-(naphthalen-1-yl)-CH(CH3)- 118-120 140. H CH3 (S)-(naphthalen-1-yl)-CH(CH3)- 117-120 141. H CH3 (R)-(naphthalen-2-yl)-CH(CH3)- 100-103 142. H CH3 (S)-(naphthalen-2-yl)-CH(CH3)- 89-91 143. H CH3 4-(C6H5)-C6H4-CH(CH3)- 81-88 144. H CH3 1,1, 2,3, 3-pentamethylindan-5-yl-CH (CH3)- resinous 145. H CH3 (R)-cyclohexyl-CH(CH3)- resinous 146. H CH3 (S)-cyclohexyl-CH (CH3)-resinous 147. H C2H5 (R)-cyclohexyl-CH(CH3)- resinous 148. H C2H5 (S)-cyclohexyl-CH(Ch3)- resinous Example R1 R2 R4 +) m.p. [°C] No. 149. H C2H5 4-Br-C6H4-CH(CH3)- resinous 150. H C2H5 4-F-C6H4-CH (CH3)-97-98 151. H C2H5 (R)-C6H5CH(CH3)- 77-80 152. H C2H5 (S)-C6H5CH(CH3)- resinous 153. H C2H5 3, 4-Cl2C6H3-CH(CH3)- 148-150 154. H C2H5 3-ClC6H4-CH(CH3)- resinous 155. H C2H5 4-F3C-C6H4-CH(CH3)- resinous 156. H C2Hs (S)-4-CH30-C6H4-CH (CH3)- resinous 157. H C2H5 (S)-4-CH3-C6H4-CH (CH3)-55-58 158. H C2H5 (R)-4-CH3-C6H4-CH(CH3)- 63-67 159. H C2H5 (S)-4-Br-C6H4-CH (CH3)-resinous 160. H C2H5 (R)-4-Br-C6H4-CH (CH3)-resinous 161. H C2H5 S)-4-F-C6H4-CH (CH3)-resinous 162. H C2H5 (R)-4-F-C6H4-CH (CH3)-resinous 163. H C2H5 (S)-4-Cl-C6H4-CH(CH3)- resinous 164. H C2H5 (R)-4-Cl-C6H4-CH(CH3)- resinous 165. H C2H5 (R)-4-Cl-C6H4-CH(CH3)- 98-105 166. H C2H5 (S)-4-NO2-C6H4-CH(CH3)- 98-105 167. H C2H5 (R)-3-CH30-C6H4-CH (CH3)-resinous 168. H C2H5 (S)-3-CH30-C6H4-CH (CH3)- resinous 169. H C2H5 (R)-4-CH3O-C6H4-CH(CH3)- resinous 170. H C2H5 4-F3C-O-C6H4-CH (CH3)-122-124 171. H C2H5 4-tert-butyl-C6H4-CH (CH3)-93-96 172. H C2H5 (R)-4-(benzyloxy)-C6H4-CH(CH3)- resinous 173. H C2H5 (S)-4-(benzyloxy)-C6H4-CH(CH3)- resinous 174. H C2H5 (R)-(naphthalen-1-yl)-CH(CH3)- 107-111 175. H C2H5 (S)-(naphthalen-1-yl)-CH(CH3)- 111-112 176. H C2H5 (R)- (naphthalen-2-yl)-CH (CH3)- 117-119 177. H C2H5 (S)-(naphthalen-2-yl)-CH(CH3)- 115-117 178. H C2H5 4-C6H5-C6H4-CH(CH3)- 53-70 179. H C2H5 1,1, 2,3, 3-pentamethylindan-5-yl-CH(CH3)- resinous 180. H3CS C2H5 S)-4-Cl-C6H4-CH (CH3)-128-131 181. H CH3CHF (R)-4-CH3-C6H4-CH (CH3)-resinous 182. H CH3CHF (R)-4-F-C6H4-CH (CH3)-resinous 183. H CH3CHF (R)-4-Cl-C6H4-CH(CH3)- resinous 184. H CH3CHF 4-F3C-O-C6H4-CH (CH3)-142-151 185. H CH3CHF 4-tert-butyl-C6H4-CH (CH3)-102-115 186. H CH3CHF (S)-4-F-C6H4-CH(CH3)- resinous 187. H CH3CHF (S)-4-CI-C6H4-CH (CH3)-resinous 188. H CH3CHF (S)-4-Br-C6H4-CH (CH3)- resinous Example R'R'R m. p. [°C] No. 189. H CH3 (2, 2-difluorobenzodioxole-5-yi) C (C2H5) H- resinous 190. H CH3 (R-C6H5CH (CH2CH3)- 65-120 191. H CH3 (S)-C6H5CH (CH2CH3)- 63-92 192. H C2H5 (R)-C6H5CH (CH2CH3)-resinous 193. H C2H5 (S)-C6H5CH (CH2CH3)- resinous 194. X H CH3 (R)-C6H5-CH2-O-CH2-CH2-CH (CH3)-48-53 195. H CH3 (S)-C6H5-CH2-O-CH2-CH2-CH (CH3)-65-66 196. H C2H5 (R)-C6H5-CH2-O-CH2-CH2-CH (CH3)-70-72 197. H C2H5 (S)-C6H5-CH2-0-CH2-CH2-CH (CH3)- 67-69 198. H CH3 (S)-2-H3C-O-C6H4-CH (CH3)-Oil 199. H C2H5 (S)-2-H3C-O-C6H4-CH (CH3)-64-69 200. H CH3 4-cyclo-C6H1,-C6H4-CH (CH3)-Oil 201. H C2H5 4-cyclo-C6H11-C6H4-CH (CH3)-110-113 202. H CH3 4-(H3C) 2CH-C6H4-CH (CH3)-Oil 203. H C2H5 4- (H3C) 2CH-C6H4-CH (CH3)- 75-77 204. H CH3 110-112 I s 205. H CZHs * Oil I 0 206. H CH3 62-67 I 207. H C2H5 59-64 I\ 208. H CH3 83-88 I r 209. H C2H5 Oil A 210. H CH3 (S)-2, 4-CI2-C6H3-CH (CH3)- 92-94 211. H C2H5 S)-2, 4-CI2-C6H3-CH (CH3)-45-47 212. SOCH3 C2H5 (S)-4-CI-C6H4-CH (CH3)-96-108 213. SO2CH3 C2H5 (S)-4-CI-C6H4-CH (CH3)- Oil 214. SCH3 C2H5 (S)-4-CH3-C6H4-CH (CH3)-60-66 215. SCH3 C2H5 (S)-4-F-C6H4-CH (CH3)-88-96 216. SCH3 C2H5 (S)-4-Br-C6H4-CH (CH3)-138-141 Example R1 R2 R4 +) m.p. [°C] No. 217. SCH3 C2H5 4-cis-(butan-2-yl)cyclohexyl- 69-72 218. SOCH3 C2H5 (S)-4-CH3-C6H4-CH (CH3)- Oil 219. S02CH3 C2H5 (S)-4-CH3-C6H4-CH (CH3)-Oil 220. SOCH3 C2H5 (S)-4-F-C6H4-CH CH3)- Oil 221. S02CH3 C2H5 (S)-4-F-C6H4-CH (CH3)- Oil 222. S02CH3 C2H5 (S)-4-Br-C6H4-CH CH3)- 65-105 223. SCH3 C2H5 4-tert.-butyl-C6H4-191-193 224. SCH3 C2H5 4-F3CO-C6H4-CH2-CH2-103-105 225. OCH3 C2H5 cis-4-tert.-butyl-cyclo-C6H11- 123-131 226. SO2CH3 C2H5 4-tert.-butyl-C6H4-205-211 227. SOCH3 C2H5 4-tert.-butyl-C6H4-240-243 228. SOCH3 C2H5 4-cis-(butan-2-yl)cyclohexyl- Oil 229. S02CH3 C2H5 4-cis-(butan-2-yl)cyclohexyl- Oil 230. S02CH3 C2H5 4-F3CO-C6H4-CH2-CH2-162-167 231. SOCH3 C2H5 4-F3CO-C6H4-CH2-CH2-146-149 232. H C2H5 4-tert.-butyl-C6H4-CH (CH3)- Oil 233. H CH3 (R)-2-H3C-O-C6H4-CH(CH3)- Oil 234. H C2H5 (R)-2-H3C-O-C6H4-CH(CH3)- 63-68 235. H CH3 (R) -2, 4-Cl2-C6H3-CH(CH3)- 84-90 236. H C2H5 (R) -2, 4-CI2-C6H3-CH (CH3)- 46-51 237. H C2H5 2-F-C6H4-CH(CH3)- 92-95 238. H CH3 2-CI-6-F-C6H3-CH (CH3)- 106-109 239. H C2H5 2-Cl-6-F-C6H3-CH(CH3)- 91-95 240. H CH3 2-F-C6H4-CH (CH3)- 104-105 241. H CH3 (2-methyl-1,3-dioxan-2-yl)-CH(CH3)- 100-103 242. H H2H5 (2-methyl-1,3-dioxan-2-yl)-CH(CH3)- Oil 243. H CH3 (2,5, 5-trimethyl-1, 3-dioxan-2-yl)-CH (CH3)- 100-102 244. H C2H5 (2,5, 5-trimethyl-1,3-dioxan-2-yl)-CH(CH3)- Oil 245. H CH3 2, 4-F2-C6H3-CH (CH3)- 139-140 246. H C2H5 2, 4-F2-C6H3-CH (CH3)- 113-115 247. H CH3 4-CI-2-F-C6H3-CH (CH3)- 106-109 248. H C2H5 4-CI-2-F-C6H3-CH (CH3)- 97-99 249. OCH3 C2H5 S)-4-F-C6H4-CH CH3)- Oil 250. OCH3 C2H5 (S)-4-CI-C6H4-CH (CH3)- Oil 251. OCH3 C2H5 (S)-4-Br-C6H4-CH (CH3)- Oil 252. a C2H5 cis-4-tert.-butyl-cyclo-C6H11- 102-105 253. b C2H5 cis-4-tert.-butyl-cyclo-C6H11- Oil 254. c C2H5 cis-4-tert.-butyl-cyclo-C6H11- Oil 255. d C2H5 cis-4-tert.-butyl-cyclo-C6H11- Oil 256. e C2H5 cis-4-tert.-butyl-cyclo-C6H11- Oil

Example R1 R2 R4 +) m.p. [°C] No. 257. f C2H5 cis-4-tert.-butyl-cyclo-C6H11- 110-143 258. C2H5 cis-4-tert.-butyl-cyclo-C6H11-75-90 259. h C2H5 cis-4-tert.-butyl-cyclo-C6H11- 78-85 260. i C2H5 cis-4-tert.-butyl-cyclo-C6H"-Oil 261. CN C2H5 cis-4-tert.-butyl-cyclo-C6H11- 151-153 262. OCH3 C2H5 4-cis-(butan-2-yl) cyclohexyl-58-69 263. OH C2H5 4-cis-(butan-2-yi) cyclohexyl-Oil 264. k C2H5 4-cis-(butan-2-yl) cyclohexyl-Oil 265. H CH3 4-F2HCO-C6H4-CH (CH3)-90-91 266. H C2H5 4-F2HCO-C6H4-CH (CH3)-102-103 267. H CH3 4-F2HC-CF2O-C6H4-CH(CH3)- 85-86 268. H C2H5 4-F2HC-CF2O-C6H4-CH (CH3)-82-83 m. p. = melting point + (S) refers always to the configuration of CH (CH3) at the nitrogen atom; and * indicates the position at which the radical is bound to the remainder of the molecule a: H3CO-C (O)-CH2-S- ; b: H3CO-CH2CH2-S-; c: H3CO-C (O)-CH2CH2-S-; d: H3CO-CH2CH2-O-; e: H3CO-CH2CH2-O-CH2CH2-O-; f: HO-C (O)-CH2-S- ; g: H3C-CH2-O-; h: (H3C) 2CH-O- ; i: HC#C-CH2-O-; k: H5C6-CH2-O- 2. Examples of action against pests The action of the compounds of the formula I against pests was demonstrated by the following experiments: The active compounds were formulated a. for testing the activity against Aphis gossypii, Tetranychus urticae, Myzus persi- cae, and Aphis fabae, as 50: 50 acetone: water solutions amended with 100 ppm Kinetic O (surfactant), b. for testing the activity against Spodoptera eridania as a 10.000 ppm solution in a mixture of 35% acetone and water, which was diluted with water, if needed, c. for testing the activity against Nilaparvata lugens and Sogatella furcifera as a 20: 80 acetone: water solution. Surfactant (Alkamuls EL 620) was added at the rate of 0.1% (vol/vol).

After the experiments were completed, in each case the lowest concentration was determined at which the compound still caused an 75 to 100% inhibition or mortality in comparison with untreated controls (limit or minimal concentration).

Cotton Aphid (Aphis gossypii) Cotton plants in the cotyledon stage (variety'Delta Pine') are infested with approxi- mately 100 laboratory-reared aphids by placing infested leaf sections on top of the test plants. The leaf sections are removed after 24 hr. The cotyledons of the intact plants are dipped into gradient solutions of the test compound. Aphid mortality on the treated plants, relative to mortality on check plants, is determined after 5 days.

In this test, compounds of examples nos 1,4, 5,6, 7,8, 13,14, 18,19, 20,58, 62,65, 66,68, 76,80, 91,101, 108,114, 115,116, 118,119, 120,121, 122,126, 150,152, 156,157, 158,159, 160,161, 162,163 and 189 at 300 ppm showed over 75% mortality in comparison with untreated controls.

Twospotted Spider Mite (Tetranychus urticae) Lima bean plants in the 1St leaf-pair stage (variety'Henderson') are infested with ap- proximately 100 laboratory-reared mites per leaf by placing infested leaf sections on top of the test plants. The leaf sections are removed after 24 hr. The foliage of the in- tact plants is dipped into gradient solutions of the test compound. Mite mortality is de- termined after 5 days.

In this test, compounds of examples nos. 1,5, 52 56,57, 58,59, 60,78, 82,84, 87,90, 91,101, 115,119 and 120 at 300 ppm showed over 75% mortality in comparison with untreated controls.

Green Peach Aphid (Myzus persicae) Pepper plants in the 2nd leaf-pair stage (variety'California Wonder') are infested with approximately 40 laboratory-reared aphids by placing infested leaf sections on top of the test plants. The leaf sections are removed after 24 hr. The leaves of the intact plants are dipped into gradient solutions of the test compound. Aphid mortality on the treated plants, relative to mortality on check plants, is determined after 5 days.

In this test, compounds of examples nos. 1,4, 5,6, 7,8, 13,14, 19,20, 55,57, 89, 106,107, 109, 114,115, 116,118, 119,120, 121,122, 123,125, 126,152, 156,157, 158,159, 160,161, 162,163 and 189 at 300 ppm showed a 100% mortality in comparison with untreated controls.

Bean Aphid (Aphis fabae) Nasturtium plants in the 1St leaf-pair stage (variety'Mixed Jewel') are infested with ap- proximately 25 laboratory-reared aphids by placing infested cut plants on top of the test plants. The cut plants are removed after 24 hr. The foliage and stem of the test plants

are dipped into gradient solutions of the test compound. Aphid mortality is determined after 3 days.

In this test, compounds of examples nos. 1,5, 6,76, 120,126, 149,161 and 163 at 300 ppm showed over 75% mortality in comparison with untreated controls.

Southern armyworm (Spodoptera eridania), 2nd instar larvae Foliage of two Sieva lima beans plants at the first expanded true-leaf stage that are contained within a single 3.8 cm square plastic pot are dipped into the test solution with agitation for 3 seconds and allowed to dry in a hood. The pot is then placed in a 25.4 cm plastic zipper top bag and infested with ten 2nd instar caterpillars. At 5 days, obser- vations are made of mortality, reduced feeding, or any interference with normal molting.

In this test, compounds of examples nos. 51,80, 119,159, 161 and 163 at 300 ppm showed over 75% mortality in comparison with untreated controls.

Brown Plant Hopper (Nilaparvata lugens) White-backed Plant Hopper (Sogatella furcifera) Potted rice plants of 3-4 weeks of age are sprayed with 10 ml of the test solution using air driven hand atomizer (Devillbis atomizer) at 1.7 bar. The treated plants are allowed to dry for about 1 hour and covered with Mylar cages. The plants are inoculated with 10 adults of each species (5 male and 5 females) and kept at 25-27oC and 50-60% hu- midity for 3 days. Mortality is assed after 24,48 and 72 hours after treatment. Dead insects are usually found in the water surface. Each treatment is replicated once.

In this test, compounds I at 500 ppm showed over 75% mortality of Nilaparvata lugens in comparison with untreated controls.

In this test, compounds I at 500 ppm showed over 75% mortality of Sogatella furcifera in comparison with untreated controls.