WO1999063822A1 - Use of substituted 2,4-diamino-1,3,5-triazines for animal pest control - Google Patents

Abstract

The invention relates to the use of partially known substituted 2,4-diamino-1,3,5-triazines of formula (I), wherein A, Z, R?1, R2 and R3¿ have the meanings cited in the description, in animal pest control. The invention also relates to methods for the production of and agents containing said triazines, in addition to novel compounds of formula (I).

Description

Use of substituted 2,4-diamino-l, 3,5-triazines for controlling animal pests

The invention relates to the use of partially known substituted 2,4-

Diamino-l, 3,5-triazines for controlling animal pests, in particular insects, arachnids and nematodes, which occur in agriculture, in forests, in the protection of stored goods and materials, and in the hygiene sector.

It is known that certain substituted 2,4-diamino-1,3,5-triazines are herbicidal

Have properties (cf. US 3 816 419, US 3 932 167, EP 191 496. EP 273 328, EP 411 153, WO 90/09378, WO 97/00254, WO 97/08156, DE 19 641 691, DE 19 641 693, DE 19 641 694). However, an insecticidal activity of these compounds has not been disclosed.

It has now been found that the substituted 2,4-diamino-1,3,5-triazines of the formula (I)

in which

A represents a single bond, alkanediyl, oxaalkanediyl or thiaalkanediyl,

R 1 stands for amino, for formylamino, or for optionally substituted alkylamino, dialkylamino, alkylcarbonylamino, N-alkyl-N-alkylcarbonylamino, alkoxycarbonylamino, N-alkyl-N-alkoxycarbonylamino, dialkylaminoalkylideneamino or alkenylcarbonylamino, R ^ represents hydrogen, halogen or in each case optionally substituted alkyl, alkoxy, alkylthio, alkylsulfmyl, alkylsulfonyl, alkenyl or alkynyl,

R.3 represents alkyl or cycloalkyl, and

Z for an optionally substituted radical from the series phenyl, naphthyl,

Tetralinyl, decalinyl, indanyl, indenyl, furyl, benzofuryl, dihydrobenzofuryl, thienyl, benzothienyl, dihydrobenzothienyl, isobenzofuryl, dihydroisobenzofuryl, isobenzothienyl, dihydroisobenzothienyl, pyrrolyl, isolylololololololololololololololololololololololololololololololololololololololindolylololololololololololololololololololololololololololololololololololololololololololololololololololololoxol

Thiazolyl, benzthiazolyl, benzimidazolyl, indazolyl, oxadiazolyl, thiadiazolyl, pyrazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, cinnolinyl, phthalazinyl,

very good for controlling animal pests, especially insects,

Arachnids and nematodes are suitable.

The compounds of the formula (I) contain at least one center of chirality and can be present in various enantiomeric (R- and S-configured) or diastereomeric forms. The invention relates both to the use of the individual enantiomeric or diastereomeric forms of the compounds of the formula (I) and to the mixtures of these forms.

Formula (I) provides a general definition of the substituted 2,4-diamino-1,3,5-triazines which can be used according to the invention.

Preferred substituents or ranges of the radicals listed in the formulas mentioned above and below are defined below.

A preferably represents a single bond, C _j -Cg-alkanediyl, C 1 -C ₆ -oxaalkanediyl or C _r C ₆ ~ thiaalkanediyl. Rl preferably represents amino, formylamino, each optionally substituted by cyano, halogen or C ₄ -C ₄ alkoxy C ₁ -C ₆ alkylamino, di (C j -C ₆ alkyl) amino, C _} -C ₆ alkylcarbonylamino, NC] -C ₆ - alkyl-N- Cj-Cö-alkylcarbonylamino, C] -C ₆ -alkoxycarbonylamino, N-Ci-Cg-alkyl-

NC i -Cg-alkoxycarbonyl 1-amino or di-C 1 -Cg-alky lamino-C i -Cg-alky lidene-amino or for C ₂ -C ₆ alkenylcarbonylamino.

R2 preferably represents hydrogen, halogen, in each case optionally substituted by cyano, halogen, hydroxyl, C 1 -C 4 -alkoxy or C 1 -C 4 -alkylthio

C, -C ₆ alkyl, C _r C ₆ alkoxy, C _r C ₆ alkylthio, C, -C ₆ alkylsulfonyl or C _j -Cg alkylsulfonyl, or in each case optionally substituted by halogen C ₂ -C ₆ alkenyl or C ₂ -C ₆ alkynyl.

R ^ is preferably C _j -Co alkyl or C ₃ -C ₆ cycloalkyl.

Z preferably represents an optionally substituted radical from the series

Phenyl, naphthyl, tetralinyl, decalinyl, indanyl, indenyl, furyl, benzofuryl, dihydrobenzofuryl, thienyl, benzothienyl, dihydrobenzothienyl, isobenzofienyl, dihydroisobenzofuryl, isobenzothienyl, dihydroisobenzothienyl, benzolindolyl, oxolindolyl, pyrolindolyl, indolylolylololindolyl, pyrolindolyl, indolylindolyl, pyrolindolyl, indolylololindolyl, indolylindolyl, pyrolindolyl, pyrolindolyl Benzoxazolyl, thiazolyl, benzothiizolyl, benzimidazolyl, indazolyl, oxadiazolyl, thiadiazolyl, pyrazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, cinnolinyl, phthalazinyl,

the possible substituents are preferably selected from the following list:

Hydroxy, amino, cyano, nitro, carbamoyl, sulfamoyl, halogen, each optionally substituted by hydroxy, cyano or halogen -CC ₆ alkyl, C _r C ₆ alkoxy, C _] -C ₆ alkylamino or di (C _| - C ₆ alkyl) amino, in each case counter optionally substituted by halogen C _j -Cg alkylcarbonyl, C _j -C ₆ alkoxycarbonyl, Ci-Cg-alkylcarbonylamino, Ci-Cg-alkylaminocarbonyl, di- (C _r C ₆ -alkyl) aminocarbonyl, Cι-C ₆ - Alkylthio, C _] -C ₆ -alkylsulfinyl, C _r C ₆ - alkylsulfonyl, Ci-Cg-alkylsulfonylamino, Cι-C ₆ -alkylaminosulfonyl or di-C _j -Cg-alkylaminosulfonyl, each optionally by hydroxy, cyano,

Nitro, halogen, C1-C4-alkyl, -C -C4-haloalkyl, Cι -C4-alkoxy or Ci - C4-haloalkoxy substituted phenyl or phenoxy, and in each case optionally substituted by halogen methylenedioxy or ethylenedioxy.

particularly preferably represents a single bond, methylene (-CH2-),

Dimethylene (ethane-l, 2-diyl, -CH CH ₂ -), ethylidene (ethane-l, l-diyl, -CH (CH ₃ ) -), oxaethanediyl (-CH O-), thiaethanediyl (-CH ₂ S -), trimethylene (propane-l, 3-diyl, -CH ₂ CH ₂ CH ₂ -), propylidene (propane-l, l-diyl, -CH (C ₂ H ₅ ) -), propane-l, 2- diyl (-CH (CH ₃ ) CH ₂ -), 2-methyl-propane-l, 3-diyl (-CH ₂ CH (CH ₃ ) CH -), l-oxa-propane-l, 3-diyl (- CH ₂ CH O-), 2-oxa-propane

1,3-diyl (-CH ₂ OCH ₂ -), tetramethylene (butane-1,4-diyl, -CH ₂ CH ₂ CH CH -), butane-1,3-diyl (-CH (CH ₃ ) CH ₂ CH ₂ -), butane-2,3-diyl (-CH (CH ₃ ) CH (CH ₃ ) -), 2-methyl-butane-l, 3-diyl (-CH (CH) CH (CH ₃ ) CH ₂ -), l-oxa-butane-l, 3-diyl (-CH (CH ₃ ) CH ₂ O-), pentane-l, 3-diyl (-CH (C ₂ H ₅ ) CH ₂ CH ₂ -) , 1-oxa-pentane-1,3-diyl (-CH (C ₂ H ₅ ) CH ₂ O-), 2-oxapentane-1,4-diyl (-CH (CH ₃ ) CH OCH -) or 2-oxa-hexane-1,4-diyl (-CH (C ₂ H ₅ ) CH ₂ OCH ₂ -).

particularly preferably stands for amino, for formylamino, for methylamino, ethylamino, dimethylamino, acetylamino, propionylamino, each optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy. n- or i-butyroylamino, N-methyl-N-acetylamino, N-ethyl-N-acetylamino, N-methyl-N-propionylamino, methoxycarbonylamino, ethoxycarbonylamino, n- or i-propoxycarbonylamino, N-methyl-N-methoxycarbonylamino, N-ethyl-N-methoxycarbonylamino, N-methyl-N-ethoxycarbonylamino, for dimethylaminomethyleneamino, 1-propen-2-yl-carbonylamino or 2-methyl-propen-l -yl-carbonylamino. R ^ particularly preferably represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, each optionally substituted by cyano, fluorine, chlorine, bromine, hydroxyl, methoxy, ethoxy or methylthio. , s- or t-butyl, or for 1-propen-2-yl or 2-methyl-propen-l-yl.

R3 particularly preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.

Z particularly preferably represents an optionally substituted radical from the

Phenyl, Naphthyl, Tetralinyl, Decalinyl, Indanyl, Indenyl, Furyl, Benzofuryl, Dihydrobenzofüryl, Thienyl, Benzothienyl, Dihydrobenzo-thienyl, Isobenzofuryl, Dihydroisobenzofuryl, Isobenzo thienyl, Dihydroisobenzylindolyl, Isolenzolindolyl, Isolenzolindolyl, Indolylindolyl, Isolenzolindolyl, Indolylindolyl, Isolenzolylol, Indolylol, Isolenzol, Isolobolyl, Indolo dioxolyl, oxazolyl, benzoxazolyl, thiazolyl, benzthiazolyl, benzimidazolyl,

Indazolyl, oxadiazolyl, thiadiazolyl, pyrazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, cinnolinyl, phthalazinyl,

where the possible substituents are in particular selected from the following list:

Hydroxy, amino, cyano, nitro, carbamoyl, sulfamoyl, fluorine, chlorine, bromine, each optionally substituted by hydroxy, cyano, fluorine or chlorine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t -Butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino or dimethylamino, each optionally substituted by fluorine and / or chlorine, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, acetylamino, propionylamino, n- or i-butyroylamino, methylaminocarbonyl , Ethylaminocarbonyl, n- or i-propylaminocarbonyl, di- methylaminocarbonyl, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, methylsulfonyl- amino, ethylsulfonylamino, n- or i-propylsulfonylamino, methylaminosulfonyl, ethylaminosulfonyl, n- or i-propylaminosulfonyl, or dimethylaminosulfonyl, each optionally by hydroxy, cyano, nitro, fluorine, chlorine, methyl, ethyl, n- or i Propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy or trifluoromethoxy-substituted phenyl or phenoxy, as well as methylenedioxy or fluorine and / or chlorine which may be substituted

Ethylenedioxy.

A very particularly preferred group of substituted 2,4-diamino-1,3,5-triazines which can be used according to the invention are those compounds of the formula (I) in which

A stands for a single bond,

Rl represents amino, acetylamino, propionylamino, dimethylaminomethyleneamino, 1-propen-2-yl-carbonylamino or 2-methyl-propen-l-yl-carbonylamino,

R2 for each methyl, ethyl, n-, i-propyl, n-butyl, 1-propen-2-yl or 2-methyl-propene, optionally substituted by hydroxy, fluorine, chlorine, bromine, cyano, methoxy, ethoxy or methylthio l-yl stands,

R ^ represents methyl, ethyl, n-, i-propyl or n-butyl, and

Z for an optionally substituted radical from the series phenyl, naphthyl,

Tetralinyl, decalinyl, indanyl, indenyl, furyl, benzofuryl, dihydrobenzo-furyl, thienyl, benzothienyl, dihydrobenzothienyl, isobenzo furyl, dihydro-isobenzofuryl, isobenzo thienyl, dihydroisobenzothienyl, pyrrolyl, indolyl, Isoindolyl, indolinyl, isoindolinyl, benzdioxolyl, oxazolyl, benzoxazolyl, thiazolyl, benzthiazolyl, benzimidazolyl, indazolyl, oxadiazolyl, thiadiazolyl, pyrazolyl, pyridyl, pyrimidinyl,

where the possible substituents are in particular selected from the following list:

Hydroxy, amino, cyano, nitro, carbamoyl, sulfamoyl, fluorine, chlorine, bromine, each optionally substituted by hydroxy, cyano, fluorine or chlorine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t -Butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino or dimethylamino, in each case optionally substituted by fluorine and / or chlorine, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, acetylamino, propionylamino, n- or i-butyroylamino, methylaminocarbonyl , Ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylaminocarbonyl, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl , Ethylsulfonyl, n- or i-propylsulfonyl, methylsulfonylamino, ethylsulfonylamino, n- or i-propylsulfonylamino, methylaminosulfonyl, ethylaminosulfonyl, n- or i -Propylaminosulfonyl, or dimethylaminosulfonyl, each optionally by hydroxy, cyano, nitro, fluorine, chlorine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl. Methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy or trifluoromethoxy substituted phenyl or phenoxy, and in each case optionally substituted by fluorine and or chlorine-substituted methylenedioxy or ethylenedioxy.

Another very particularly preferred group of substituted 2,4-diamino-1,3,5-triazines which can be used according to the invention are those compounds of the formula (I) in which A represents dimethylene (ethane-1,2-diyl, -CH ₂ CH -) or oxaethanediyl (-CH ₂ O-),

R for amino, acetylamino, propionylamino, dimethylaminomethyleneamino, 1-

Propen-2-yl-carbonylamino or 2-methyl-propen-l-yl-carbonylamino,

R2 stands for methyl, ethyl, n-, i-propyl, n-butyl, propenyl or butenyl which is optionally substituted by hydroxy, fluorine, chlorine, bromine, cyano, methoxy, ethoxy or methylthio,

R ^{J represents} methyl, ethyl, n-, i-propyl or n-butyl, and

Z for an optionally substituted radical from the series phenyl, naphthyl, tetralinyl, decalinyl, indanyl, indenyl, furyl, benzofuryl, dihydrobenzofuryl, thienyl, benzothienyl, dihydrobenzothienyl, isobenzofuryl, dihydro-isobenzofuryl, isobenzothylothienyl, diol , Isoindolyl, indolinyl, isoindolinyl, benzdioxolyl, oxazolyl, benzoxazolyl, thiazolyl, benzthiazolyl, benzimidazolyl, indazolyl, oxadiazolyl, thidiazolyl, pyrazolyl, pyridyl, pyrimidinyl,

where the possible substituents are in particular selected from the following list:

Hydroxy, amino, cyano, nitro, carbamoyl, sulfamoyl, fluorine, chlorine, bromine, each optionally substituted by hydroxy, cyano, fluorine or chlorine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t -Butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino or dimethylamino, in each case optionally substituted by fluorine and / or chlorine, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxy- carbonyl, acetylamino, propionylamino, n- or i-butyroylamino, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylaminocarbonyl, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, methylsulfonylamino, ethylsulfonylamino, n- or i-propylsulfonylamino, methylaminosulfonyl, ethylaminosulfonyl, ethylaminosulfonyl Propylaminosulfonyl, or dimethylaminosulfonyl, each optionally by hydroxy, cyano, nitro, fluorine, chlorine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy or trifluoromethoxy-substituted phenyl or phenoxy, and also methylene dioxy or ethylenedioxy optionally substituted by fluorine and / or chlorine.

Another very particularly preferred group of substituted 2,4-diamino-1,3,5-triazines which can be used according to the invention are those compounds of the formula (I) in which

A stands for a single bond,

Rl represents amino, acetylamino, propionylamino, dimethylaminomethyleneamino, 1-propen-2-yl-carbonylamino or 2-methyl-propen-l-yl-carbonylamino,

R2 for each methyl, ethyl, n-, i-propyl, n-butyl, 1-propen-2-yl or 2-methyl-propene, optionally substituted by hydroxy, fluorine, chlorine, bromine, cyano, methoxy, ethoxy or methylthio l-yl stands,

R ^ represents methyl, ethyl, n-, i-propyl or n-butyl, and

Z represents an optionally substituted radical from the series phenyl, benzofuryl, benzodioxolyl, pyridyl or thienyl, where the possible substituents are in particular selected from the following list:

Fluorine, chlorine, bromine, methyl, methylthio or methylenedioxy.

Another very particularly preferred group of substituted 2,4-diamino-1,3,5-triazines which can be used according to the invention are those compounds of the formula (I) in which

A represents dimethylene (ethane-1,2-diyl, -CH CH -) or oxaethanediyl (-CH ₂ O-),

Rl stands for amino, acetylamino, propionylamino, dimethylaminomethyleneamino, 1-propen-2-yl-carbonylamino or 2-methyl-propen-1-yl-carbonylammo,

R2 for each methyl, ethyl, n-, i-propyl, n-butyl, l-propen-2-yl or 2-methyl-propene optionally substituted by hydroxyl, fluorine, chlorine, bromine, cyano, methoxy, ethoxy or methylthio l-yl stands,

R ^ represents methyl, ethyl, n-, i-propyl or n-butyl, and

Z for an optionally substituted radical from the series phenyl, benzofuryl

Thienyl, benzdioxolyl or pyridyl,

where the possible substituents are in particular selected from the following list:

Fluorine, chlorine, bromine, methyl, methylthio or methylenedioxy. The general definitions or explanations of residues or explanations listed above or in preferred areas can be combined with one another, that is to say also between the respective areas and preferred areas. They apply accordingly to the end products as well as to the preliminary and intermediate products.

According to the invention, preference is given to the compounds of the formula (I) in which there is a combination of the meanings listed above as preferred (preferred).

According to the invention, particular preference is given to the compounds of the formula (I) in which there is a combination of the meanings listed above as being particularly preferred.

According to the invention, very particular preference is given to the compounds of the formula (I) in which there is a combination of the meanings listed above as being particularly preferred.

Optionally substituted radicals can be mono- or polysubstituted, whereby in the case of multiple substitutions the substituents can be the same or different.

In the case of terminal heteroatoms, oxaalkanediyl and thiaalkanediyl are to be understood such that Z is bonded to the heteroatom.

In the definitions are the hydrocarbon chains, such as alkyl, alkenyl or

Alkynyl - also in combination with heteroatoms, such as in alkoxy or alkylthio - in each case straight-chain or branched.

Halogen generally represents fluorine, chlorine. Bromine or iodine, preferably for fluorine, chlorine or bromine, especially for fluorine or chlorine. The substituted 2,4-diamino-1,3,5-triazines of the general formula (I) to be used according to the invention are known (cf. DE 19 802 236, DE 19 816 055, DE 19 846 516) and / or can according to known processes are produced (cf. US 3 816 419, US 3 932 167, EP 191 496, EP 273 328, EP 411 153, WO 90/09378, WO 97/00254, WO 97/08156, DE 19 641 691, DE 19 641 693, DE

19 641 694, DE 19 711 825, production examples).

The active compounds of the general formula (I) are suitable for controlling animal pests, preferably arthropods and nematodes, in particular insects and arachnids, which occur in agriculture, in forests, in the protection of stored goods and materials and in the hygiene sector. They are effective against normally sensitive and resistant species as well as against all or individual stages of development. The pests mentioned above include:

From the order of the Isopoda e.g. Oniscus asellus, Armadillidium vulgare, Poreellio scaber.

From the order of the Diplopoda e.g. Blaniulus guttulatus.

From the order of the Chilopoda e.g. Geophilus carpophagus, Scutigera spec.

From the order of the Symphyla e.g. Scutigerella immaculata.

From the order of the Thysanura e.g. Lepisma saccharina.

From the order of the Collembola e.g. Onychiurus armatus.

From the order of the Orthoptera, for example Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis, Schistocerca gregaria. From the order of the Dermaptera, for example, Forficula auricularia.

From the order of the Isoptera e.g. Reticulitermes spp ..

From the order of the anoplura e.g. Pediculus humanus corporis, Haematopinus spp., Linognathus spp.

From the order of the Mallophaga e.g. Trichodectes spp., Damalinea spp.

From the order of the Thysanoptera e.g. Hercinothrips femoralis, Thrips tabaci.

From the order of the Heteroptera e.g. Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp.

From the order of the Homoptera e.g. Aleurodes brassicae, Bemisia tabaci, Tria- leurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp., Puliphigoxyl - losiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii,

Aspidiotus hederae, Pseudococcus spp. Psylla spp.

From the order of the Lepidoptera, for example Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, LithocoUetis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp. Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Spodoptera exigua, Mamestra brassicae, Panolis flammea, Prodenia litura, Spodoptera spp., Trichoplapsia spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinea pellionella, Hofmannophila pseudospretella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magna- nima, Tortrix viridana.

From the order of the Coleoptera e.g. Anobium punctatum, Rhizopertha dominica, Acanthoscelides obtectus, Bruchidius obtectus, Hylotrupes bajulus, Agelastica alni,

Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp., Sitophilus spp., Otiorrhynchus sulcatordimidhmpphppm, spp. , Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallonstit zealandica.

From the order of the Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp.,

Monomorium pharaonis, Vespa spp.

From the order of the Diptera e.g. Aedes spp., Anopheles spp., Culex spp., Drosilila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp.,

Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa.

From the order of the Siphonaptera e.g. Xenopsylla cheopis, Ceratophyllus spp ..

From the order of the Arachnida e.g. Scorpio maurus, Latrodectus mactans.

From the order of the Acarina e.g. Acarus siro, Argas spp., Ornithodoros spp., Der- manyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp.,

Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp ..

Plant-parasitic nematodes include e.g. Pratylenchus spp., Radopholus spp., Ditylenchus spp., Tylenchulus spp., Heterodera spp., Globodera spp., Melodogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp., Tylenchus spp. Helicotylenchus spp., Rotylenchus spp., Tylenchulus spp ..

The compounds of the general formula (I) which can be used according to the invention are notable for strong insecticidal activity.

They can be used with particularly good success for combating plant-damaging insects, for example against onion flies (Hylemyia antiqua) or against cockroaches (Plutella xylostella).

The active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, natural and synthetic substances impregnated with active substances, and very fine encapsulations in polymeric substances .

These formulations are made in a known manner, e.g. by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and or foam-forming agents.

If water is used as an extender, organic solvents can, for example, also be used as auxiliary solvents. The following are essentially suitable as liquid solvents: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable Oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.

Possible solid carriers are: e.g. Ammonium salts and natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite, synthetic granules from inorganic and organic flours and granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems; as emulsifying and / or foaming agents are possible: e.g. nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkyl aryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; Possible dispersants are: e.g. Lignin sulfite liquor and methyl cellulose.

Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations. Other additives can be mineral and vegetable oils.

Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.

The formulations generally contain between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90%. The active compounds can be present in commercially available formulations and in the use forms prepared from these formulations in a mixture with other active compounds, such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth-regulating substances or herbicides. To the

Insecticides include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, chlorinated hydrocarbons, phenylureas, substances produced by microorganisms, etc.

Particularly cheap mixing partners are e.g. the following:

Fungicides: aldimorph, ampropylfos, ampropylfos potassium, andoprim, anilazine, azaconazole, azoxystrobin, benalaxyl, benodanil, benomyl, benzamacril, benzamacrylic isobutyl, bialaphos, binapacryl, biphenyl, bitertanol, biolaphididolate, sulfonidolate, sulfupidazolate, blasticidazolate, blasticidol, benzolupiridazolate, blasticidolate, sulfupidazolate, blasticidolate, sulfupidazolate, blasticidium polysulfate Capsimycin, Captafol,

Captan, Carbendazim, Carboxin, Carvon, Quinomethionate (Chlobenthiazon), Chlorfenazol, Chloroneb, Chloropicrin, Chlorothalonil, Chlozolinat, Clozylacon, Cufraneb, Cymoxanil, Cyproconazol, Cyprodinil, Cyprofuramoblumolanozan , Difenoconazole, dimethirimol, dimethomorph, diniconazole, diniconazole-M, dinocap,

Diphenylamine, Dipyrithione, Ditalimfos, Dithianon, Dodemoφh, Dodine, Drazoxolon, Ediphenphos, Epoxiconazol, Etaconazol, Ethirimol, Etridiazol, Famoxadone, Fenapanil, Fenarimol, Fenbuconazol, Fenfurampomorphonfimentropinpimentin, Ferin Fluazinam, flumetover, fluoromid, fluquinconazole, flurprimidol, flusilazole, flusulfamide,

Flutolanil, Flutriafol, Folpet, Fosetyl-Alminium, Fosetyl-Sodium, Fthalid, Fuberidazol, Furalaxyl, Furametpyr, Furcarbonil, Furconazol, Furconazol-cis, Furmecyclox, Guazatin, Hexachlorobenzol, Hexaconazinadinadinadin, Imacazinadadinoid, Hymexilinozinoid, Hymexilinozinoid, Hymexilinozinoid iodocarb, ipconazole, iprobenfos (IBP), iprodione, irumamycin, isoprothiolan. Isovaledione, kasugamycin, kresoxim-methyl, copper preparations such as: copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, oxin copper and Bordeaux mixture, copper, Mancozeb, Maneb, Meferimzone, Mepanipyrim, Mepronil, Metalaxyl, Metconazol, Methasulfocarb, Methfüroxam, Metiram, Metomeclam, Metsuifovax, Mildianiline, Myclobolin Nickel dimethyldithiocarbamate, nitrothalisopropyl, Nuarimol, Oftirace, Oxadixyl, Oxamocarb, Oxolinicacid, Oxycarboxim,

Oxyfenthiin, paclobutrazole, pefurazoate, penconazole, pencycuron, phosdiphen, pimaricin, piperalin, polyoxin, polyoxorim, probenazole, procloraz, procymidone, propamocarb, propanosine sodium, propiconazole, propineb, pyrazophimolone, quinoxinone PCNB), sulfur and sulfur preparations, Tebuconazole, Tecloftalam, Tecnazen, Tetcyclacis,

Tetraconazole, thiabendazole, Thicyofen, Thifluzamide, thiophanate-methyl, thiram, Tioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, Triazbutil, triazoxide, Trichlamid, tricyclazole, Tridemoφh, triflumizole, triforine, triticonazole, uniconazole, validamycin A, vinclozolin, Viniconazol , Zarilamide, Zineb, Ziram and Dagger G, OK-8705, OK-8801, - (1,1-dimethylethyl) -ß- (2-phenoxyethyl) -lH-1,2,4-triazole-1-ethanol, α - (2,4-dichlorothenyl) -ß-fluoro-b-propyl-1 H-1, 2,4-triazole-1-ethanol, α- (2,4-dichlorothenyl) -ß-methoxy-a-methyl- 1 H-1, 2,4-triazole-1-ethanol, α- (5-methyl-1,3-dioxan-5-yl) -ß - [[4- (trifluoromethyl) phenyl] methylene] - 1 H-1, 2,4-triazol-1-ethanol, (5RS, 6RS) -6-hydroxy-2,2,7,7-tetramethyl-5- (1H-l, 2,4-triazol-l-yl ) -3-octanone, (E) -a- (methoxyimino) -N-methyl-2-phenoxy-phenylacetamide, {2-methyl-1 - [[[[1 - (4-methylphenyl) ethyl] amino] - carbonyl] -propyl} -carbamic acid- 1 -isopropyl ester 1 - (2,4-dichloφhenyl) -2- (1 H- 1, 2,4-triazole-1 -yl) -ethanone-O- (phenylmethyl) oxime, 1 - (2-methyl-1-naphthalenyl) - 1 H-pyrrole-2,5-dione, 1 - (3, 5-dichloro phhenyl) -3- (2-propenyl) -2, 5 ~ pyrrolidinedione, 1 - [(diiodomethyl) sulfonyl] -4-methyl-benzene, 1 - [[2- (2,4-dichlorophenyl) -l, 3-dioxolan-2-yl] methyl] - lH-imidazole, l - [[2- (4-chloro-phenyl) -3-phenyloxiranyl] methyl] -lH-l, 2,4-triazole, l- [l- [2 - [(2,4- Dichlθφhenyl) methoxy] phenyl] - ethenyl] - 1 H-imidazole, 1-methyl-5-nonyl-2- (phenylmethyl) -3-pyrrolidinol, 2 ', 6'-di-bromo-2-methyl-4 '-trifluoromethoxy-4'-trifluoromethyl-1, 3-thiazole-5-carboxanilide, 2,2-dichloro-N- [l- (4-chloro-phenyl) -ethyl] -l-ethyl-3-methyl-cyclopropanecarboxamide , 2,6-dichloro-5- (methylthio) -4-pyrimidinyl-thiocyanate, 2,6-dichloro-N- (4-trifluoromethylbenzyl) benzamide, 2,6-dichloro-N - [[4- (trifluoromethyl) -phenyl] -methyl] - benzamide, 2- (2,3,3-triiodo-2-propenyl) -2H-tetrazole, 2 - [(l-methylethyl) sulfonyl] -5- (trichloromethyl) -l, 3,4-thiadiazole, 2- [[6-Deoxy-4-O- (4-O-methyl-β-D-glycopyranosyl) aD-glucopyranosyl] amino] -4-methoxy-lH-pyrrolo [2,3-d] pyrimidine-5- carbonitrile, 2-aminobutane, 2-bromo-2- (bromomethyl) -pentanitrile, 2-chloro-N- (2,3-dihydro-1,1,3-trimethyl-1 H-inden-4-yl) -3 -pyridinecarboxamide, 2-chloro-N- (2,6-dimethylphenyl) -N-

(isothiocyanatomethyl) acetamide, 2-phenylphenol (OPP), 3,4-dichloro-1 - [4-

(difluoromethoxy) phenyl] -lH-pyrrole-2,5-dione, 3,5-dichloro-N- [cyan [(l-methyl-2-propynyl) -oxy] methyl] benzamide, 3- (1 , 1-dimethylpropyl-1-oxo-1 H-indene-2-carbonitrile, 3- [2- (4-chloro-phenyl) -5-ethoxy-3-isoxazolidinyl] pyridine, 4-chloro-2-cyano-N, N-dimethyl-5- (4-methylphenyl) -1 H-imidazole-1-sulfonamide, 4-methyl-tetrazolo [1,5-a] quinazolin-5 (4H) -one, 8- (l, l-dimethylethyl ) -N-ethyl-N-propyl-l, 4-dioxaspiro [4.5] decane-2-methanamine, 8-hydroxyquinoline sulfate, 9H-xanthene-9-carboxylic acid 2 - [(phenylamino) carbonyl] hydrazide, bis- (1-methylethyl) -3-methyl-4 ~ [(3-methylbenzoyl) -oxy] -2,5-thiophene dicarboxylate, ice-1 - (4-chloro-phenyl) -2- (1 H-1, 2,4-triazol-l-yl) cycloheptanol, cis-4- [3- [4- (l, l-dimethylpropyl) phenyl-2-methylpropyl] -

2,6-dimethyl-moφholin hydrochloride, ethyl - [(4-chloro-phenyl) -azo] cyanoacetate,

Potassium hydrogen carbonate, methane tetrathiol sodium salt, methyl 1 - (2,3-dihydro-2,2-dimethyl-1 H-inden-1-yl) - 1 H-imidazole-5-carboxy lat, methyl IN- (2.6 -dimethylphenyl) - N- (5-isoxazolylcarbonyl) -DL-alaninate, methyl-N- (chloroacetyl) -N- (2,6-dimethylphenyl) -DL-alaninate, N- (2,3-dichloro-4-hydroxyphenyl ) - 1 -methyl-cyclohexane carboxamide. N- (2,6-dimethylphenyl) -2-methoxy-N- (tetrahydro-2-oxo-3-furanyl) acetamide, N- (2,6-dimethylphenyl) -2-methoxy-N- (tetrahydro-2 -oxo-3-thienyl) -acetamide, N- (2-chloro-4-nitrophenyl) -4-methyl-3-nitro-benzenesulfonamide, N- (4-cyclohexylphenyl) -l, 4,5,6- tetrahydro-2-pyrimidinamine, N- (4-hexylphenyl) - 1, 4,5,6-tetrahydro-2-pyrimidinamine, N- (5-chloro-2-methylphenyl) -2-methoxy-N- (2nd - oxo-3-oxazolidinyl) -acetamide, N- (6-methoxy) -3-pyridinyl) -cyclopropanecarboxamide, N- [2,2,2-trichloro-l - [(chloroacetyl) -amino] -ethyl] -benzaiΗid , N- [3-chloro-4,5-bis (2-propynyloxy) phenyl] -N'-methoxy-methanimidamide, N-formyl-N-hydroxy-DL-alanine sodium salt, O, O-diethyl- [2- (dipropylamino) -2-oxoethyl] ethyl phosphoramidothioate, O-methyl-S-phenyl-phenylpropylphosphoramidothioate, S-methyl-1, 2,3-benzothia-diazole-7-carbothioate, spiro [2H] -l-benzopyran -2, r (3'H) -isobenzofuran] -3'-one. Bactericides: bronopol, dichlorophene, nitrapyrin, nickel-dimethyldithiocarbamate, kasugamycin, octhilinone, furan carboxylic acid, oxytetracycline, probenazole, streptomycin, tecloftalam, copper sulfate and other copper preparations.

Insecticides / acaricides / nematicides: Abamectin, AC 303 630, Acephat, Acrinathrin, Alanycarb, Aldicarb, Alphamethrin, Amitraz, Avermectin, AZ 60541, Azadirachtin, Azinphos A, Azinphos M, Azocyclotin, Bacillus thuringoctap, Benfus Betacyfluthrin, Bifenthrin, BPMC, Brofenprox, Bromophos A, Bufencarb, Buprofezin, Butocarboxim, Butylpyridaben, Cadusafos, Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, CGA 157 419, CGA 184699, Chlorovethoxy Carbos Chlorfluazuron, Chlormephos, Chlorpyrifos, Chloφyrifos M, Cis-Resmethrin, Clocythrin, Clofentezin, Cyanophos, Cycloprothrin, Cyfluthrin, Cyhalothrin, Cyhexatin, Cypermethrin, Cyromazin, Delta-methrin, Demeton M, Demetonur , Diazinon, Dichlofenthion, Dichlorvos, Dicliphos, Dicrotophos, Diethion, Diflubenzuron, Dimethoat, Dimethylvinphos, Dioxathion, Disulfoton, Edifenphos, Emamectin, Esfenvalerat, Ethiofencarb, Ethion, Ethofenprox, Ethoprophos, Etrimphos, Fenamiphos, Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate, Fipronil, Fluazinam,

Flucycloxuron, flucythrinate, flufenoxuron, flufenprox, fluvalinate, fonophos, formothion, fosthiazate, fubfenprox, furathiocarb, HCH, heptenophos, hexaflumuron, hexythiazox, imidacloprid, iprobefos, isazophos, isodinphaline, lamboxin, lambinoxin, lambda Lufenuron, Malathion, Mecarbam, Mevinphos, Mesulfenphos, Metaldehyde, Methacrifos, Methamidophos, Methidathion Methiocarb, Methomyl, Metolcarb, Milbemectin, Monocrotophos, Moxidectin, Naled, NC 184, NI 25, Nitenpyram, Mylox, Oxeth, Oxeth, Oxeth, Oxeth Oxydeprofos, Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos M, Pirimiphos A, Profenofos, Promecarb, Propaphos, Propoxur, Prothiofos, Prothoat, Pyrachophinosin, Pyrachlophenos thion, pyresmethrin, pyrethrum, pyridaben, pyrimidifen, pyriproxifen, quinalphos, RH 5992, Salithion, Sebufos, Silafluofen, Sulfotep, Sulprofos, Tebufenozid, Tebufenpyrad, Tebupirimiphos, Teflubenzuron, Tefluthrin, Temephos, Terbam, Terbufos, Tetrachlorvinphos, Thiafenox, Thiodicarb, Thinofionin, Trinominium, Trinofluoromin, Trinofluorosin , Triazophos, Triazuron, Trichlorfon, Triflumuron, Trimethacarb, Vamidothion, XMC, Xylylcarb, YI 5301, YI 5302, Zetamethrin.

A mixture with other known active ingredients, such as herbicides or with fertilizers and growth regulators, is also possible.

When used as insecticides, the active compounds according to the invention can also be present in their commercially available formulations and in the use forms prepared from these formulations in a mixture with synergists. Synergists are compounds through which the action of the active ingredients is increased without the added synergist itself having to be active.

The active substance content of the use forms prepared from the commercially available formulations can vary within wide ranges. The active substance concentration of the use forms can be from 0.0000001 to 95% by weight of active substance, preferably between 0.0001 and 1% by weight.

The application takes place in a customary manner adapted to the application forms.

When used against hygiene pests and pests of stored products, the active ingredient is distinguished by an excellent residual action on wood and clay and by a good stability to alkali on limed substrates. Production examples: Example 1

step 1

A mixture of 74.5 g (0.30 mol) of 3- (3-bromo-thiophen-2-yl) -l-ethyl-propylamine (racemic), 36 g of 33% hydrochloric acid and 100 ml of methanol is added in a water jet vacuum Dry evaporated. The residue is mixed with 25.2 g (0.30 mol) of cyano-guanidine (“dicyandiamide”) and this mixture is heated at 160 ° C. to 170 ° C. for two hours.

99 g (90% of theory) of l- [3- (3-bromo-thiophen-2-yl) -l-ethyl-propyl] - biguanide hydrochloride (racemate) are obtained as an amorphous product.

Level 2

A solution of 3.0 g (55 mmol) of sodium methylate in 30 ml of methanol is added dropwise with stirring to a mixture of 18.5 g (50 mmol) of l- [3- (3-bromo-thiophene- 2-yl) -l-ethyl-propyl] -biguanide hydrochloride (racemic), 6.0 g (50 mmol) of methyl 2-fluoro-2-methyl-propionate and 100 ml of methanol are added and the reaction mixture is added for 15 hours Room temperature (about 20 ° C) stirred. Then it is shaken with diethyl ether, the organic phase is separated off, washed with water, dried with sodium sulfate and filtered. The solvent is carefully distilled off from the filtrate in a water jet vacuum.

10.7 g (53% of theory) of 2-amino-4- [3- (3-bromo-thiophene-2-yl) -l-ethyl-propylamino] -6- (l-fluoro-l-methyl) are obtained -ethyl) -l, 3,5-triazine (racemate) as an amorphous residue.

Example 2

Analogously to the procedure described in Example 1, the compound 2-amino-4- (1-methyl-3-thiophene-2-yl) -6-methoxymethyl-1,3,5-triazine (racemate) is first prepared.

Then a mixture of 2.0 g (6.8 mmol) of 2-amino-4- (l-methyl-3-thiophene-2-yl) -6-methoxymethyl-l, 3,5-triazine (racemic) and 20 ml of acetic anhydride heated to 120 ° C for two hours. After cooling, this mixture is diluted with 200 ml of water and stirred for one hour at room temperature (approx. 20 ° C.). The water is then decanted off, the residue is taken up in 50 ml of methylene chloride, washed with water, dried with sodium sulfate and filtered. The solvent is carefully distilled off from the filtrate in a water jet vacuum. 0.50 g (22% of theory) of 2-acetylamino-4- (1-methyl-3-thiophene-2-yl) -6-methoxymethyl-1,3,5-triazine (racemate) is obtained as an amorphous residue.

Analogously to the preparation examples 1 and 2, the compounds of the formula (I) listed in Table 1 below can also be prepared, for example. Further examples of the compounds of the general formula (I) which can be used according to the invention can be found, for example, in the following patent applications or patents: US Pat. No. 3,816,419, US Pat. No. 3,932,167, EP 191,496, EP 273,328, EP 411,153 / WO 90/09378 , WO 97/00254, WO 97/08156, DE 19 641 691, DE 19 641 693, DE 19 641 694, DE 19 711 825.

Table 1: Examples of the compounds of the formula (I)

The logP values given in Table 1 were determined in accordance with EEC Directives 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) on a phase reversal column (C 18). Temperature 43 ° C.

(a) Eluents for determination in the acidic range: 0.1% aqueous phosphoric acid, acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile - corresponding measurement results are marked in Table 1 with ^a) .

(b) eluents for determination in the neutral range: 0.01 molar aqueous phosphate buffer solution, acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile - corresponding measurement results are marked in Table 1 with ^b) .

The calibration was carried out using unbranched alkan-2-ones (with 3 to 16 carbon atoms) whose logP values are known (determination of the logP values on the basis of the retention times by linear interpolation between two successive alkanones).

The lambda max values were determined using the UV spectra from 200 nm to 400 nm in the maxima of the chromatographic signals. The listed compounds of Preparation Examples 1 to 127 are new and also the subject of the present application.

Examples of use:

Example A Hylemyia test

Solvent: 100 parts by weight of acetone emulsifier: 1900 parts by weight of methanol

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent and the mixture is diluted

Concentrate with methanol to the desired concentrations.

A specified amount of active compound preparation of the desired concentration is pipetted onto a standardized amount of synthetic feed. After the methanol has evaporated, about 20 eggs of the onion fly (Hylemyia antiqua) are placed on the feed.

After the desired time, the death of the eggs or larvae is determined in%. 100% means that all animals have been killed; 0% means that no animals have been killed.

In this test, for example, the compound according to Preparation Example 2, with an exemplary active ingredient concentration of 0.05%, shows a kill of 100% after 7 days. Example B: Plutella test

Solvent: 100 parts by weight of acetone emulsifier: 1900 parts by weight of methanol

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the concentrate is diluted with methanol to the desired concentrations.

A specified amount of active compound preparation of the desired concentration is pipetted onto a standardized amount of synthetic feed. After the methanol has evaporated, approx. 200-300 cabbage cockroach eggs (Plutella xylostella) are added to the feed.

After the desired time, the death of the eggs or larvae is determined in%. 100% means that all animals have been killed; 0% means that no animals have been killed.

In this test, for example, the compounds according to Preparation Examples 1 and 3, with an exemplary active compound concentration of 0.1%, show a kill of 95 to 100% after 7 days.

Example C Phaedon larva test

Solvent: 7 parts by weight of dimethylformamide emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted to the desired concentration with water containing emulsifier.

Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and populated with larvae of the horseradish beetle (Phaedon cochleariae) while the leaves are still moist.

After the desired time, the kill is determined in%. 100% means that all beetle larvae have been killed; 0% means that no beetle larvae have been killed.

In this test, e.g. the compound according to preparation example 4 at an exemplary active ingredient concentration of 0.1%, a kill of 100% after 7 days.

Claims

claims

1. Use of substituted 2,4-diamino-1,3,5-triazines of the formula (I)

in which

A represents a single bond, alkanediyl, oxaalkanediyl or thiaalkanediyl,

Rl represents amino, formylamino, or optionally substituted alkylamino, dialkylamino, alkylcarbonylamino, N-alkyl-N-alkylcarbonylamino, alkoxycarbonylamino, N-alkyl-N-alkoxycarbonylamino, dialkylaminoalkylideneamino or alkenylcarbonylamino,

R represents hydrogen, halogen or in each case optionally substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkenyl or alkynyl,

R represents alkyl or cycloalkyl, and

Z represents an optionally substituted radical from the phenyl series,

Naphthyl, tetralinyl, decalinyl, indanyl, indenyl, furyl, benzofuryl.

Dihydrobenzofuryl, thienyl, benzothienyl, dihydrobenzothienyl, isobenzofuryl, dihydroisobenzofuryl, isobenzothienyl, dihydroisobenzothienyl, pyrrolyl, indolyl, isoindolyl, indolinyl, isoindolinyl, benzdi- oxolyl, oxazolyl, oxazolyl, oxazolyl, oxazolyl, oxazolyl, oxazolyl, oxazolyl, oxazolyl, oxazolyl, oxazolyl, oxazolyl, oxazolyl, oxazolyl, oxazolyl, oxazolyl imidazolyl, indazolyl, oxadiazolyl, thiadiazolyl, pyrazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, cinnolinyl, phthalazinyl,

to control animal pests.

2. Use of compounds of formula I according to claim 1, in which

A represents a single bond, C _j -Cg-alkanediyl, C _j -C ₆ -oxaalkanediyl or C _] -C ₆ -thiaalkanediyl,

R ¹ for amino, for formylamino, for each optionally by cyano,

Halogen or CC ₄ alkoxy substituted Cj-Cg-alkylamino, Di (C _r

C ₆ -alkyl) amino, C _r C ₆ -alkylcarbonylamino, NC, -C ₆ -alkyl-NC _r C ₆ -alkylcarbonyl-amino, C _r C ₆ -alkoxycarbonylamino, NC _r C ₆ -

Alkyl-NC _] -C ₆ -alkoxycarbonyl-amino or Di-C _| -C ₆ -alkylamino-C _r C ₆ -alkylidenamino or represents C ₂ -C ₆ -alkenylcarbonylamino.

R ² for hydrogen, halogen, each optionally substituted by cyano, halogen, hydroxy, C 1 -C ₄ -alkoxy or C i -C - alkylthio

C ₆ alkyl, C _r C ₆ alkoxy, C, -C ₆ alkylthio, C _r C ₆ alkyl sulfionyl or C _j -Cg alkyl sulfonyl, or in each case optionally substituted by halogen C ₂ -C ₆ alkenyl or C ₂ -C ₆ alkynyl.

R ^{3 represents} C _r C ₆ alkyl or C ₃ -C ₆ cycloalkyl.

Z represents an optionally substituted radical from the phenyl series,

Naphthyl, tetralinyl, decalinyl, indanyl, indenyl, furyl, benzofuryl,

Dihydrobenzofuryl, thienyl, benzothienyl, dihydrobenzothienyl, isobenzofuryl, dihydroisobenzofuryl, isobenzothienyl, dihydroisobenzothienyl, pyrrolyl, indolyl, isoindolyl, indolinyl, isoin dolinyl, benzdioxolyl, oxazolyl, benzoxazolyl, thiazolyl, benzthiazolyl, benzimidazolyl, indazolyl, oxadiazolyl, thiadiazolyl, pyrazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinolinyl, quinoxalinyl

where the possible substituents are selected from the following list:

Hydroxy, amino, cyano, nitro, carbamoyl, sulfamoyl, halogen, in each case optionally substituted by hydroxy, cyano or halogen, C _r C ₆ alkyl, C _] -C ₆ alkoxy, CC ₆ alkylamino or di (C ₁ -C ₆ -alkyl) amino, in each case optionally substituted by halogen, C _j -C ₆ -alkylcarbonyl, C _] -C ₆ -alkoxycarbonyl, C _] -C ₆ -alkylcarbonylamino, C _] -C ₆ -alkylaminocarbonyl, di- (C] - C ₆ alkyl) amino carbonyl, C _r C ₆ alkylthio, C, -C ₆ alkylsulfinyl, C j -C ₆ alkylsulfonyl, C _] -C ₆ alkylsulfonylamino, C _j -Cg alkylaminosulfonyl or di-C _j -Cg-alkylaminosulfonyl, each optionally substituted by hydroxyl, cyano, nitro, halogen, Ci-C / j-alkyl, Ci -C-pHalogenalkyl, C1-C4- alkoxy or C -C -Cj-haloalkoxy or

Phenoxy, and in each case optionally substituted by halogen methylenedioxy or ethylenedioxy

to control animal pests.

3. Use of compounds of formula (I) according to claim 1, in which

A for a single bond, for methylene (-CH ₂ -), dimethylene (ethane

1,2-diyl, -CH ₂ CH -), ethylidene (ethane-l, l-diyl, -CH (CH ₃ ) -), oxa-ethanediyl (-CH ₂ O-), thiaethanediyl (-CH ₂ S- ), Trimethylene (propane

1,3-diyl, -CH ₂ CH ₂ CH -), propylidene (propane-l, l-diyl, -CH (CH ₅ ) -), Propane-l, 2-diyl (-CH (CH ₃ ) CH ₂ -), 2-methyl-propane-l, 3-diyl (-CH ₂ CH (CH ₃ ) CH ₂ -), l-oxa-propane 1,3-diyl (-CH ₂ CH ₂ O-), 2-oxa-propane-1,3-diyl (-CH ₂ OCH ₂ -), tetramethylene (butane-1,4-diyl, -CH CH ₂ CH ₂ CH ₂ -), butane-1,3-diyl (-CH (CH ₃ ) CH ₂ CH ₂ -), butane-2,3-diyl (-CH (CH ₃ ) CH (CH ₃ ) -), 2 -Methyl-butane-l, 3-diyl

(-CH (CH ₃ ) CH (CH ₃ ) CH ₂ -), 1 -oxa-butane-1,3-diyl

(-CH (CH ₃ ) CH O-), pentane-1,3-diyl (-CH (C ₂ H ₅ ) CH ₂ CH ₂ -), 1-oxapentane-1,3-diyl (-CH ( C ₂ H ₅ ) CH ₂ O-), 2-oxapentane-1,4-diyl

(-CH (CH ₃ ) CH ₂ OCH ₂ -) or 2-oxa-hexane-1,4-diyl (-CH (C ₂ H ₅ ) CH OCH ₂ -).

Rl for amino, for formylamino, for methylamino, ethylamino, dimethylamino, acetylamino, propionylamino, n- or i-butyroylamino, N-methyl-N-acetylamino, N-, each substituted by cyano, fluorine, chlorine, methoxy or ethoxy Ethyl-N-acetyl-amino,

N-methyl-N-propionyl-amino, methoxycarbonylamino, ethoxycarbonylamino, n- or i-propoxycarbonylamino, N-methyl-N-methoxycarbonylamino, N-ethyl-N-methoxycarbonylamino, N-methyl-N-ethoxycarbonyl -amino, represents dimethylaminomethyleneamino, l-propen-2-yl-carbonylamino or 2-methyl-propen-l-yl-carbonylamino.

R for hydrogen, fluorine, chlorine, bromine, for each optionally by

Cyano, fluorine, chlorine, bromine, hydroxy, methoxy, ethoxy or methylthio substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or for l-propen-2-yl or 2-methyl-propen-l-yl.

R3 represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl. for an optionally substituted radical from the series phenyl, naphthyl, tetralinyl, decalinyl, indanyl, indenyl, furyl, benzofuryl, dihydrobenzofuryl, thienyl, benzothienyl, dihydrobenzothienyl, isobenzofuryl, dihydroisobenzofuryl, isobenzothienyl, dihydroolol, dihydroolol, dihydroolol, dihydroololol indolinyl, isoindolinyl, Benz dioxolyl, oxazolyl, benzoxazolyl, thiazolyl, benzothiazolyl, Benz imidazolyl, indazolyl, oxadiazolyl, thiadiazolyl, pyrazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, Chin oxalinyl, cinnolinyl, phthalazinyl is

where the possible substituents are selected from the following list:

Hydroxy, amino, cyano, nitro, carbamoyl, sulfamoyl, fluorine, chlorine, bromine, each optionally by hydroxy, cyano, fluorine or

Chlorine-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, Methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino or dimethylamino, each optionally substituted by fluorine and / or chlorine, acetyl, propionyl, n- or i-butyroyl,

Methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, acetylamino, propionylamino, n- or i-butyroylamino, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylaminocarbonyl, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfmyl, ethylsulfinyl, n- or i-pronvlsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, methylsulfonylamino, ethylsulfonylamino, n- or i-propylsulfonylamino, Methylaminosulfonyl, ethylaminosulfonyl, n- or i-propylaminosulfonyl, or dimethylaminosulfonyl, each optionally by hydroxy, cyano, nitro, fluorine, chlorine, methyl, ethyl, n- or i-

Propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromefhoxy or trifluoromethoxy-substituted phenyl or phenoxy, and also methylene dioxy or ethylenedioxy optionally substituted by fluorine and / or chlorine

to control animal pests.

4. Use of compounds of formula I according to claim 1, in which

A stands for a single bond,

R1 is amino, acetylamino, propionylamino, dimethylaminomethylene-amino, l-propen-2-yl-carbonylamino or 2-methyl-propen-l-yl-carbonylamino,

R2 for each methyl, ethyl, n-, i-propyl, n-butyl, l-propen-2-yl or 2-methyl-propene optionally substituted by hydroxyl, fluorine, chlorine, bromine, cyano, methoxy, ethoxy or methylthio l-yl stands,

R ^{J represents} methyl, ethyl, n-, i-propyl or n-butyl, and

Z represents an optionally substituted radical from the phenyl series,

Naphthyl, tetralinyl, decalinyl, indanyl, indenyl, furyl, benzofuryl. Dihydrobenzofuryl, thienyl, benzothienyl, dihydrobenzothienyl, isobenzofuryl, dihydroisobenzofuryl, isobenzothienyl, dihydroisobenzothienyl, pyrrolyl, indolyl, isoindolyl, indolinyl, isoindolinyl, benzdioxolyl, oxazolyl, oxazolyl, oxazolyl, oxazolyl, oxazolyl, oxazolyl, oxazolyl, oxazolyl, oxazolyl, oxazolyl, oxazolyl, oxazolidyl Thiadiazolyl, pyrazolyl, pyridyl, pyrimidinyl, where the possible substituents are selected from the following list:

Hydroxy, amino, cyano, nitro, carbamoyl, sulfamoyl, fluorine, chlorine, bromine, each optionally by hydroxy, cyano, fluorine or

Chlorine-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, Methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino or dimethylamino, each optionally substituted by fluorine and / or chlorine, acetyl, propionyl, n- or i-butyroyl,

Methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, acetylamino, propionylamino, n- or i-butyroylamino, mefhylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylaminocarbonyl, methylthio, ethylthio, n- or i-propylthio n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, methylsulfonylamino, ethylsulfonylamino, n- or i-propylsulfonylamino, Methylaminosulfonyl, ethylaminosulfonyl, n- or i-propylaminosulfonyl, or dimethylaminosulfonyl, each optionally by hydroxy, cyano, nitro, fluorine, chlorine, methyl, ethyl, n- or i-

Propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy or trifluoromethoxy substituted phenyl or phenoxy , and in each case optionally substituted by fluorine and / or chlorine methylenedioxy or ethylenedioxy

to control animal pests.

5. Compounds of formula (I)

characterized in that A, R ¹ , R ² , R ³ and Z have the meanings given in the following table:

6. pesticide, characterized by a Gehali n one

A compound of formula (I) according to claim 1.

7. A method of combating pests, characterized in that compounds of the formula (I) according to Claim 1 are allowed to act on pests and / or their habitat. Process for the preparation of pesticides, characterized in that compounds of the formula (I) according to Claim 1 are mixed with extenders and / or surface-active agents.