DE19923317A1 - Use of new and known tin-tetrazole compounds as herbicides, insecticides, acaricides and nematicides - Google Patents

Abstract

New and known substituted tin-tetrazole compounds (I) are used as herbicides and for combating animal pests. Use of substituted tin-tetrazole compounds of formula (I), as herbicides or for combating animal pests. R<1> = alkyl, phenyl (optionally substituted) or heteroaryl (optionally substituted) and R<2> = alkyl, cycloalkyl (optionally substituted) or phenyl (optionally substituted). An Independent claim is included for new compounds of formulae (Ia) and (Ib). R = halo, NO2, CN, OH, T, TO, TS, alkylcarbonyl or Q; Q = phenyl, phenoxy, phenylthio or pyrimidinyloxy (all optionally substituted by halo, NO2, CN, T, TO, TS or Q'); Q' = phenoxy (optionally substituted by halo, NO2, CN, T, TO or TS); T = (halo)alkyl and Het = 5-6 membered, optionally benzo-fused heteroaryl group which contains 1-4 N (or N-O), O and S heteroatoms (optionally substituted by 1-3 halo, NO2, CN, 1-4C (halo)alkyl, 1-4C (halo)alkoxy or 1-4C (halo)alkylthio), provided that the following compounds are excluded: (a) (Ia; R = p-nitro-phenyl, p-methoxy-phenyl or 2-(4-methyl-phenyl)-phenyl) and (b) (Ib; R<2> = n-butyl and Het = 3-methyl-pyrid-2-yl).

Description

The present invention relates to the use of substituted tin tetrazoles for controlling animal pests and as herbicides, new tin tetrazoles and process for their preparation.

Certain tin tetrazoles and processes for their preparation are already known (see, e.g., WO 93 00341; J. Org. Chem. (1991), 56 (7), 2395-400; Bull. Chem. Soc. Yep (1973), 46 (7), 2176-80; J. Organometal. Chem. (1971), 33 (3), 337-46; J. Organometal. Chem. (1975), 92 (3), 303-9); about using this verb is used to control animal pests or as herbicides nothing became known.

It has been found that substituted tin tetrazoles of the formula (I)

in which
R ^{1 represents} alkyl, optionally substituted phenyl or optionally substituted hetaryl and
R ^{2 represents} alkyl, optionally substituted cycloalkyl or optionally substituted phenyl,
can be used very well to control animal pests and as herbicides.

The substituted tin tetrazoles which can be used according to the invention are those which Formula (I) defined.

Preferred substituents or ranges of the radicals listed in the formulas mentioned above and below are defined below.
R ¹ preferably represents C ₁ -C ₄ alkyl, optionally single to triple (in particular single or double), identical or different by halogen, nitro, cyano, hydroxy, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ - haloalkyl, C ₁ -C ₄ -haloalkoxy, C ₁ -C ₄ haloalkylthio, C ₁ -C ₄ alkyl carbonyl, phenyl, phenoxy, phenylthio and pyrimidinyloxy substituted phenyl, where phenyl, phenoxy, phenylthio or pyrimidinyloxy can be monosubstituted to trisubstituted (in particular single or double), identical or different, by halogen, nitro, cyano, C ₁ -C ₄ -alkyl, C ₁ -C ₄ - alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ -haloalkoxy, C ₁ -C ₄ - haloalkylthio, in each case optionally monosubstituted or disubstituted by identical or different halogen, nitro, cyano , C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ - alkylthio, C 1-C ₄ haloalkyl, C ₁ -C ₄ -haloalkoxy, C ₁ -C ₄ haloalkyl thio substituted Phenylam inocarbonyl-C ₁ -C ₄ alkyl, pyridylaminocarbonyl C ₁ -C ₄ alkyl or phenoxy,
or for optionally single to triple (in particular single or double) identical or different by halogen, nitro, cyano, hydroxy, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ - haloalkoxy, C ₁ -C ₄ -haloalkylthio, phenyl, phenoxy and phenylthio-substituted 5- or 6-membered, optionally benzo-fused hetaryl with 1 to 4 identical or different hetero atoms, such as N -, S or O atoms, including possible N-oxides (in particular pyridyl, pyridyl-N-oxide, pyrimidinyl, tetrazolyl, furyl, thienyl, thiazolyl and oxazolyl),
where phenyl, phenoxy or phenylthio can be substituted once to three times (in particular once or twice), identically or differently, by halogen, nitro, cyano, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ haloalkoxy and C ₁ -C ₄ haloalkylthio.
R ² preferably represents C ₁ -C ₄ alkyl, each optionally mono- or disubstituted, identically or differently, by halogen and C ₁ -C ₄ alkyl-substituted phenyl or C ₅ -C ₇ cycloalkyl.
R ¹ particularly preferably represents methyl, optionally one or two times, identical or different by fluorine, chlorine, bromine, nitro, cyano, hydroxy, methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio, trifluoromethyl, difluoromethyl, fluoromethyl , 1-chloro-1-ethyl, 1-fluoro-1-ethyl, trifluoromethoxy, trifluoromethylthio, methylcarbonyl, ethylcarbonyl, phenyl, phenoxy, phenylthio and pyrimidinyloxy substituted phenyl, where phenyl, phenoxy, phenylthio or pyrimidinyloxy are single or double, the same or can be substituted differently by fluorine, chlorine, bromine, nitro, cyano, methyl, ethyl, methoxy, methylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, each optionally mono- or disubstituted, identically or differently, by fluorine, chlorine, bromine, nitro, cyano , Methyl, ethyl, methoxy, methylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio substituted phenylaminocarbonylmethyl, pyridylaminocarbonylmethyl or phenoxy,
or for each optionally single or double, identical or different, substituted by fluorine, chlorine, bromine, nitro, cyano, methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, phenyl, phenoxy and phenylthio, optionally benzo-condensed pyridyl, pyridyl-N-oxide, pyrimidyl, tetrazolyl, furyl, thienyl, thiazolyl and oxazolyl, where phenyl, phenoxy or phenylthio can be mono- or disubstituted, identically or differently, by fluorine, chlorine, bromine, nitro, cyano, methyl , Ethyl, methoxy, methylthio, trifluoromethyl, trifluoromethoxy and trifluoromethylthio.
R ² particularly preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclohexyl or phenyl.
R ¹ very particularly preferably represents methyl, optionally single or double, identical or different by fluorine, chlorine, nitro, cyano, hydroxy, methyl, methoxy, methylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, methylcarbonyl, phenyl, phenoxy, phenylthio and pyrimidinyl oxy-substituted phenyl, where phenyl, phenoxy, phenylthio or pyrimidinyloxy can be substituted once or twice, identically or differently, by fluorine, chlorine, bromine, nitro, cyano, methyl, methoxy, methylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, in each case where appropriate single or double, identical or different from fluorine, chlorine, bromine, nitro, cyano, methyl, methoxy, methylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio substituted pyridylaminocarbonylmethyl or phenoxy,
or for each optionally single or double, identical or different, substituted by fluorine, chlorine, bromine, nitro, cyano, methyl, methoxy, methylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, phenyl, phenoxy and phenylthio, optionally benzo-condensed pyridyl, pyridyl-N oxide, pyrimidinyl, tetrazolyl, furyl, thienyl, thiazolyl and oxazolyl, where phenyl, phenoxy or phenylthio can be substituted once or twice, identically or differently, by fluorine, chlorine, nitro, cyano, methyl, methoxy, methylthio, trifluoromethyl, trifluoromethoxy and Trifluoromethylthio.
R ² very particularly preferably represents methyl, ethyl, n- or i-propyl, n-butyl, cyclohexyl or phenyl.
R ¹ stands for methyl, for phenyl optionally substituted once or twice, identically or differently by fluorine, chlorine, nitro, hydroxy, trifluoromethyl, trifluoromethoxy, methylthio, methylcarbonyl, phenyl, phenoxy, phenylthio and pyrimidinyloxy, phenyl, phenoxy, phenylthio or Pyrimidinyloxy single or double, identical or different which can be substituted by fluorine, chlorine, methyl, trifluoromethyl, methylthio, in each case optionally single or double, identical or different by fluorine, chlorine, ethyl, trifluoromethyl,

substituted phenoxy or pyridylaminocarbonylmethyl,
or for each optionally single or double, identical or different, optionally substituted by benzo-fused pyridyl, pyridyl-N-oxide, thienyl, furyl, pyrimidinyl or tetrazolyl substituted by chlorine, bromine, methyl, ethyl, phenoxy, chlorophenoxy or methylthio.
R ² stands for methyl, n-propyl, n-butyl, or phenyl.

The general or priority areas listed above Finitions can be between themselves, that is, between the preferred ones specified Areas can be combined as required.

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

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

Unless otherwise specified, optionally substituted radicals can be a be substituted several times or more, with the sub stituents can be the same or different.

In the definitions are the hydrocarbon chains, such as alkyl, alkanediyl, alkenyl or alkynyl - also in combination with heteroatoms, such as in alkoxy or alkylthio - each straight or branched.

Unless otherwise stated, halogen generally represents fluorine, chlorine, Bromine or iodine, preferably for fluorine, chlorine or bromine, especially for fluorine or chlorine.

The substituted tin tetrazoles of the formula (I) which can be used according to the invention are partially known (see, for example, WO 93 00341; J. Org. Chem. (1991), 56 (7), 2395-400; Bull. Chem. Soc. Yep (1973), 46 (7), 2176-80; J. Organometal. Chem. (1971), 33 (3), 337-46; J. Organometal. Chem. (1975), 92 (3), 303-9).

Substituted tin tetrazoles of the formulas (Ia) and (Ib) are new

in which
R represents phenyl substituted by halogen, nitro, cyano, hydroxy, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy, haloalkylthio, alkylcarbonyl, phenyl, phenoxy, phenylthio and pyrimidinyloxy, where phenyl, phenoxy, phenylthio or pyrimidinyloxy can each be substituted by halogen , Nitro, cyano, alkyl, alkoxy, alkylthio, halo genalkyl, haloalkoxy, haloalkylthio, optionally substituted by halogen, nitro, cyano, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy, halo genalkylthio, with the proviso that compounds with

excluded are;
and

in which
R ^{2 has} the meaning given above and
Hetaryl has the meaning given above; with the proviso that the compound with R ² = n-butyl and

is excluded.

The new substituted tin tetrazoles of the formulas (Ia) and (Ib) are obtained if tetrazoles of the formula (II)

in which
R 'represents the meanings of R or hetaryl,

• a) with tin hydroxide derivatives of the formula (III)
  HO-Sn (R ² ) ₃ (III)
  in which
  R ^{2 has} the meaning given above,
  in the presence of a diluent;
  or
• b) with tin halide derivatives of the formula (IV)
  Hal-Sn (R ² ) ₃ (IV)
  in which
  R ^{2 has} the meaning given above and
  Hal represents halogen, preferably chlorine,

in the presence of an acid binder and optionally in the presence of a Reacts diluent.

The new substituted tin tetrazoles are generally defined by the formulas (Ia) and (Ib).
R preferably represents single to triple (in particular single or double), identical or different, by halogen, nitro, cyano, hydroxy, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio , C ₁ -C ₄ haloalkyl, C ₁ -C ₄ -Halogenalkoxy, C ₁ -C ₄ haloalkylthio, C ₁ -C ₄ alkylcarbonyl, phenyl, phenoxy, phenylthio and pyrimidinyloxy substituted phenyl, phenyl, phenoxy, phenylthio or pyrimidinyloxy can be substituted once to three times (in particular once or twice), identically or differently, by halogen, nitro, cyano, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ haloalkyl thio, in each case, if appropriate, once or twice, identically or differently by halogen, nitro, cyano, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ -haloalkoxy, C ₁ -C ₄ -haloalkylthio substitu iertes phenylaminocarbonyl-C ₁ -C ₄ alkyl, Pyridylamine ocarbonyl-C ₁ -C ₄ alkyl or phenoxy,
or optionally mono- to trisubstituted by (especially mono- or disubstituted), identically or differently by halogen, nitro, cyano, hydroxy, C ₁ -C ₄ alkyl, C 1-C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ - haloalkoxy, C ₁ -C ₄ -haloalkylthio, phenyl, phenoxy and phenylthio-substituted 5- or 6-membered, optionally benzo-fused hetaryl with 1 to 4 identical or different hetero atoms, such as N, S or O atoms, including possible N-oxides (in particular pyridyl, pyridyl-N-oxide, pyrimidinyl, tetrazolyl, furyl, thienyl, thiazolyl and oxazolyl), phenyl, phenoxy or phenylthio being simple to triple, (in particular mono- or disubstituted), can be substituted by identical or different halogen, nitro, cyano, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ haloalkoxy and C ₁ -C ₄ haloalkylthio, with the proviso that compounds in which

excluded are;
R particularly preferably represents single or double, identical or different through fluorine, chlorine, bromine, nitro, cyano, hydroxy, methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio, trifluoromethyl, difluoromethyl, fluoromethyl, 1-chloro-1-ethyl , 1-fluoro-1-ethyl, trifluoromethoxy, trifluoromethylthio, methylcarbonyl, ethylcarbonyl, phenyl, phenoxy, phenylthio and pyrimidinyloxy substituted phenyl, where phenyl, phenoxy, phenylthio or pyrimidinyloxy can be substituted once or twice, identically or differently, by fluorine, Chlorine, bromine, nitro, cyano, methyl, ethyl, methoxy, methylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, in each case, if appropriate, once or twice, identically or differently by fluorine, chlorine, bromine, nitro, cyano, methyl, ethyl, methoxy, methylthio, Trifluoromethyl, trifluoromethoxy, trifluoromethylthio substituted phenylamino carbonylmethyl, pyridylaminocarbonylmethyl or phenoxy,
or for each optionally single or double, identical or different, substituted by fluorine, chlorine, bromine, nitro, cyano, methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, phenyl, phenoxy and phenylthio, optionally benzo-condensed pyridyl, pyridyl-N-oxide, pyrimidyl, tetrazolyl, furyl, thienyl, thiazolyl and oxazolyl, where phenyl, phenoxy or phenylthio can be mono- or disubstituted, identically or differently, by fluorine, chlorine, bromine, nitro, cyano, methyl , Ethyl, methoxy, methylthio, trifluoromethyl, trifluoromethoxy and trifluoromethylthio; with the proviso that connections in which

excluded are;
R very particularly preferably represents single or double, identical or different from fluorine, chlorine, nitro, cyano, hydroxy, methyl, methoxy, methylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, methylcarbonyl, phenyl, phenoxy, phenylthio and pyrimidinyloxy substituted phenyl , where phenyl, phenoxy, phenylthio or pyrimidinyloxy, in each case mono- or disubstituted, may be substituted identically or differently by fluorine, chlorine, bromine, nitro, cyano, methyl, methoxy, methylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, in each case optionally once to twice , identical or different from fluorine, chlorine, bromine, nitro, cyano, methyl, methoxy, methylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio substituted pyridylaminocarbonylmethyl or phenoxy,
or for in each case optionally single to double, identical or different, fluorine, chlorine, bromine, nitro, cyano, methyl, methoxy, methylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, phenyl, phenoxy and phenylthio, optionally benzo-condensed pyridyl, pyridyl, N-oxide, pyrimidinyl, tetrazole, furyl, thienyl, thiazolyl and oxazolyl, where phenyl, phenoxy or phenylthio can be mono- to disubstituted, identical or different, by fluorine, chlorine, nitro, cyano, methyl, methoxy, methylthio, trifluoromethyl, Trifluoromethoxy and trifluoromethyl thio, with the proviso that compounds in which

excluded are.
Hetaryl has the meaning given above.
R ² has the meaning given above, with the proviso that the connection with
R ² = n-butyl and

is excluded.

The specified substituent definitions can be combined with one another as desired bar.  

The general or priority areas listed above Finitions can be between themselves, that is, between the preferred ones specified Areas can be combined as required.

According to the invention, preference is given to the compounds of the formulas (Ia) and (Ib), in which is a combination of the meanings listed above as preferred is present.

According to the invention, particular preference is given to the compounds of the formulas (Ia) and (Ib), in which a combination of the above is particularly preferred meanings.

Unless otherwise specified, optionally substituted radicals can be a be substituted several times or more, with the sub stituents can be the same or different.

In the definitions are the hydrocarbon chains, such as alkyl, alkanediyl, alkenyl or alkynyl - also in combination with heteroatoms, such as in alkoxy or alkylthio - each straight or branched.

Unless otherwise stated, halogen generally represents fluorine, chlorine, Bromine or iodine, preferably for fluorine, chlorine or bromine, especially for fluorine or chlorine.

If, for example, 5- (6-methoxy-quinolin-4-yl) tetrazole and trimethyl tin hydroxide are used as starting materials, the course of process (a) according to the invention can be represented by the following reaction scheme:

If, for example, 5- (fur-2-yl) tetrazole and trimethyltin chloride are used as starting materials, the course of process (b) according to the invention can be represented by the following reaction scheme:

The starting point for carrying out processes (a) and (b) according to the invention Tretrazoles of the formula (II) required are known and / or customary Methods available, such as. B. by reacting appropriate nitriles with sodium azide and triethylamine hydrochloride (see also the preparation examples).

In some cases it proves to be advantageous to convert the corresponding nitriles directly into the tin tetrazoles of the formulas (Ia) and (Ib) by reaction with trimethyltin azide [(CH ₃ ) ₃ SnN ₃ ] (cf. also the preparation examples).

The tin hydroxide derivatives to be used as starting materials Formula (III) or tin halide derivatives of the formula (IV) are generally known Compounds of organic chemistry and / or obtained by known methods Lich.  

Process (a) according to the invention is preferably carried out in the presence of a diluent carried out. Alcohols, such as methanol, are preferably usable and ethanol; Nitriles such as acetonitrile or esters such as ethyl acetate. It is also possible to work in organic-aqueous mixtures if necessary.

The reaction temperatures can be carried out when carrying out the process according to the invention Process (a) can be varied over a wide range. Generally works one at temperatures between 0 ° C and 100 ° C, preferably between 20 ° C and 80 ° C.

The procedure (a) according to the invention is carried out beforehand preferably in equimolar amounts; but it is also possible to do one or the other Use starting product in excess.

Process (b) according to the invention is preferably carried out using Diluents performed. These come in handy as diluents all inert organic solvents in question. These preferably include aliphatic and aromatic, optionally halogenated hydrocarbons such as Pentane, hexane, heptane, cyclohexane, petroleum ether, petrol, ligroin, benzene, toluene, Xylene, methylene chloride, ethylene chloride, chloroform, carbon tetrachloride, chlorine benzene and o-dichlorobenzene, ethers such as diethyl and dibutyl ether, glycol dimethyl ether and diglycol dimethyl ether, tetrahydrofuran and dioxane, ketones such as acetone, Methyl ethyl, methyl isopropyl and methyl isobutyl ketone, esters such as acetic acid methyl ester and ethyl ester, nitriles such as. B. acetonitrile and propionitrile, amides such as e.g. B. dimethylformamide, dimethylacetamide and N-methylpyrrolidone and Di methyl sulfoxide, tetramethylene sulfone and hexamethyl phosphoric acid triamide.

Process (b) according to the invention is carried out in the presence of a base. All conventional protons can be used as bases in the process according to the invention receptors are used. Alkali or alkaline earths are preferably usable hydroxides, alkali or alkaline earth hydrides, alkali or alkaline earth carbonates or hy  drug carbonates or nitrogen bases. Examples include sodium hy hydroxide, calcium hydroxide, sodium hydride, potassium carbonate, sodium hydrogen carbonate, triethylamine, dibenzylamine, diisopropylamine, pyridine, quinoline, diazabi cyclooctane (DABCO), diazabicyclonones (DBN) and diazabicycloundecene (DBU).

The reaction temperatures can be carried out when carrying out the process according to the invention Process (b) can be varied over a wide range. Generally works one at temperatures between 0 ° C and 100 ° C, preferably between 20 ° C and 80 ° C.

When carrying out the process (b) according to the invention, in general mean 1 to 2 mol, preferably 1 to 1.5 mol, per mol of compound of the formula (II) Tin halide derivative.

The end products are worked up and isolated in a generally known manner and way.

The active ingredients are suitable for good plant tolerance and inexpensive warmth blood toxicity to control animal pests, especially insects, Arachnids and nematodes, which are used in agriculture, in forests, in stock and Material protection and in the hygiene sector. You can preferably can be used as pesticides. They are sensitive to normal and resi constant species and effective against all or individual stages of development. To the Pests mentioned above include:

From the order of the Isopoda z. B. Oniscus asellus, Armadillidium vulgare, Porcellio scaber.

From the order of the Diplopoda z. B. Blaniulus guttulatus.

From the order of the Chilopoda z. B. Geophilus carpophagus, Scutigera spp.  

From the order of the Symphyla z. B. Scutigerella immaculata.

From the order of the Thysanura z. B. Lepisma saccharina.

From the order of the Collembola z. B. Onychiurus armatus.

From the order of Orthoptera z. B. Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus spp., Schistocerca gregaria.

From the order of the Blattaria z. B. Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica.

From the order of the Dermaptera z. B. Auricular Forficula.

From the order of the Isoptera z. B. Reticulitermes spp.

From the order of the Phthiraptera z. B. Pediculus humanus corporis, Haematopinus spp., Linognathus spp., Trichodectes spp., Damalinia spp.

From the order of the Thysanoptera z. B. Hercinothrips femoralis, Thrips tabaci, Thrips palmi, Frankliniella accidentalis.

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

From the order of Homoptera z. B. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigus spp., Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum 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 z. B. Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella xylostella, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Mamestra brassicae, Panolis flammea, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinea pellionella, Hofmannophila pseudospretella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana, Cnaphalocerus spp.

From the order of the Coleoptera z. B. Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma 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, Amphimallon solstitialis, Costelytra zealandica.

From the order of the Hymenoptera z. B. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.

From the order of the Diptera z. B. Aedes spp., Anopheles spp., Culex spp., Drosophila 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, Hylemyia spp., Liriomyza spp.

From the order of the Siphonaptera z. B. Xenopsylla cheopis, Ceratophyllus spp.

From the class of the Arachnida z. B. Scorpio maurus, Latrodectus mactans, Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus 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., Hemitarsonemus spp., Brevipalpus spp.

The plant parasitic nematodes include z. B. Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp., Bursaphelenchus spp.

The substances which can be used according to the invention can be used with particularly good success to control plant-damaging insects, such as. B. against the caterpillars of the Cotton capsule worm (Heliothis armigera and Heliothis virescens), the peach aphid (Myzus persicae), the larvae of the horseradish beetle (Phaedon cochleariae), the caterpillars of the cockroach (Plutella xylostella), the caterpillars of the army worm (Spodoptera exigua and Spodoptera frugiperda); as well as to combat veget harmful mites, such as B. against the common spider mite (Tetranychus urticae).

The active ingredients can be converted into the usual formulations, such as Lö solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble Che powder, granules, suspension emulsion concentrates, impregnated with active ingredient Natural and synthetic substances as well as very fine encapsulation in polymeric substances.  

These formulations are prepared in a known manner, e.g. B. by mixing of the active ingredients with extenders, i.e. liquid solvents and / or solid Carriers, optionally using surface-active agents, thus emulsifiers and / or dispersants and / or foam-producing Means.

In the case of the use of water as an extender, e.g. B. also organic Solvents are used as auxiliary solvents. As a liquid solvent essentially come into question: aromatics, such as xylene, toluene, or alkyl naphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as Chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g. B. 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.

The following are suitable as solid carriers:
e.g. B. ammonium salts and natural rock powders, such as kaolins, clays, talcum, 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: z. B. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and Ta bakstems; the following may be used as emulsifying and / or foaming agents:
e.g. B. nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for. B. alkylaryl polyglycol ethers, alkyl sulfates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; as dispersants come into question: z. B. lignin sulfite and methyl cellulose.

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

Dyes such as inorganic pigments, e.g. B. iron oxide, titanium oxide, ferro cyan 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 Active ingredient, preferably between 0.5 and 90%.

The active ingredient according to the invention can be in its commercially available formulations and in the use forms prepared from these formulations in a mixture with other active ingredients, such as insecticides, attractants, sterilants, bactericides, Acaricides, nematicides, fungicides, growth regulators or herbi ziden available. Insecticides include, for example, phosphoric acid esters, Carbamates, carboxylic acid esters, chlorinated hydrocarbons, phenylureas, substances produced by microorganisms u. a.

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

Fungicides

Aldimorph, ampropylfos, ampropylfos potassium, andoprim, anilazine, azaconazole, azoxystrobin,
Benalaxyl, benodanil, benomyl, benzamacril, benzamacrylic isobutyl, bialaphos, binapacrylic, biphenyl, bitertanol, blasticidin-S, bromuconazole, bupirimate, buthio bat,
Calcium polysulfide, capsimycin, captafol, captan, carbendazim, carboxin, carvone, quinomethionate (quinomethionate), chiobenthiazon, chlorfenazole, chloroneb, chloropicrin, chlorothalonil, chlozolinate, clozylacon, cufraneb, cymoxanil, cyprodinconazol
Debacarb, dichlorophene, diclobutrazole, diclofluanide, diclomezin, dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole, diniconazol-M, dinocap, diphenylamine, dipyrithione, ditalimfos, dithorphoxinodonine, dithorphononodine
Ediphenphos, Epoxiconazole, Etaconazole, Ethirimol, Etridiazole,
Famoxadone, fenapanil, fenarimol, fenbuconazole, fenfuram, fenitropan, fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide, ferbam, ferimzon, fluazinam, flumetover, fluoromid, fluquinconazole, flurprimolol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusilazolutol, flusulfazolutol, flusulfazolutol, flusilazolutol, flusilazolutol, flusilazolutolol Fosetyl sodium, fthalide, fuberidazole, furalaxyl, furametpyr, furcarbonil, furconazole, furconazole-cis, furmecyclox,
Guazatin,
Hexachlorobenzene, hexaconazole, hymexazole,
Imazalil, Imibenconazol, Iminoctadin, Iminoctadinealbesilat, Iminoctadinetriacetat, Iodocarb, Ipconazol, Iprobefos (IBP), Iprodione, Irumamycin, Isoprothiolan, Isovaledione,
Kasugamycin, Kresoxim-methyl, copper preparations, such as: copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, oxine-copper and Bordeaux mixture,
Mancopper, Mancozeb, Maneb, Meferimzone, Mepanipyrim, Mepronil, Metalaxyl, Metconazol, Methasulfocarb, Metrifuroxam, Metiram, Metomeclam, Metsulfovax, Mildiomycin, Myclobutanil, Myclozolin,
Nickel dimethyldithiocarbamate, nitrothal isopropyl, Nuarimol,
Ofurace, Oxadixyl, Oxamocarb, Oxolinicacid, Oxycarboxim, Oxyfenthiin,
Paclobutrazole, pefurazoate, penconazole, pencycuron, phosdiphen, pimaricin, piperalin, polyoxin, polyoxorim, probenazole, prochloraz, procymidon, propamocarb, propanosine sodium, propiconazole, propineb, pyrazophos, pyrifen, pyifenox, pyrroyilonil
Quinconazole, quintozen (PCNB),
Sulfur and sulfur preparations,
Tebuconazole, tecloftalam, tecnazene, Tetcyclacis, tetraconazole, thiabendazole, Thicyofen, Thifluzamide, thiophanate-methyl, thiram, Tioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, Triazbutil, triazoxide, Trichlamid, tricyclazole, tridemorph, triflumizole, triforine, triticonazole,
Uniconazole,
Validamycin A, vinclozolin, viniconazole,
Zarilamid, Zineb, Ziram as well
Dagger G,
OK-8705,
OK-8801,
α- (1,1-dimethylethyl) -β- (2-phenoxyethyl) -1H-1,2,4-triazole-1-ethanol,
α- (2,4-dichlorophenyl) -β-fluoro-b-propyl-1H-1,2,4-triazole-1-ethanol,
α- (2,4-dichlorophenyl) -β-methoxy-a-methyl-1H-1,2,4-triazole-1-ethanol,
α- (5-methyl-1,3-dioxan-5-yl) -β - [[4- (trifluoromethyl) phenyl] methylene] -1H-1,2,4-triazol-1-ethanol,
(5RS, 6RS) -6-hydroxy-2,2,7,7-tetramethyl-5- (1H-1,2,4-triazol-1-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-dichlorophenyl) -2- (1H-1,2,4-triazol-1-yl) -ethanone-O- (phenylmethyl) oxime,
1- (2-methyl-1-naphthalenyl) -1H-pyrrole-2, 5-dione,
1- (3,5-dichlorophenyl) -3- (2-propenyl) -2,5-pyrrolidinedione,
1 - [(diiodomethyl) sulfonyl] -4-methyl-benzene,
1 - [[2- (2,4-dichlorophenyl) -1,3-dioxolan-2-yl] methyl] -1H-imidazole,
I - [[2- (4-chlorophenyl) -3-phenyloxiranyl] methyl] -1H-1,2,4-triazole,
1- [1- [2 - [(2,4-dichlorophenyl) methoxy] phenyl] ethenyl] -1H-imidazole,
1-methyl-5-nonyl-2- (phenylmethyl) -3-pyrrolidinol,
2 ', 6'-dibromo-2-methyl-4'-trifluoromethoxy-4'-trifluoromethyl-1,3-thiazole-5-carboxanilide,
2,2-dichloro-N- [1- (4-chloropheny1) ethyl] -1-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 - [(1-methylethyl) sulfonyl] -5- (trichloromethyl) -1,3,4-thiadiazole,
2 - [[6-Deoxy-4-O- (4-O-methyl-β-D-glycopyranosyl) -aD-glucopyranosyl] amino] -4- methoxy-1H-pyrrolo [2,3-d] pyrimidine- 5-carbonitrile,
2-aminobutane,
2-bromo-2- (bromomethyl) pentandinitrile,
2-chloro-N- (2,3-dihydro-1,1,3-trimethyl-1H-1-inden-4-yl) -3-pyridinecarboxamide,
2-chloro-N- (2,6-dimethylphenyl) -N- (isothiocyanatomethyl) acetamide,
2-phenylphenol (OPP),
3,4-dichloro-1- [4- (difluoromethoxy) phenyl) -1H-pyrrole-2,5-dione,
3,5-dichloro-N- [cyan [(1-methyl-2-propynyl) oxy] methyl] benzamide,
3- (1,1-dimethylpropyl-1-oxo-1H-indene-2-carbonitrile,
3- [2- (4-chlorophenyl) -5-ethoxy-3-isoxazolidinyl] pyridine,
4-chloro-2-cyan-N, N-dimethyl-5- (4-methylphenyl) -1H-imidazole-1-sulfonamide,
4-methyl-tetrazolo [1,5-a] quinazolin-5 (4H) -one,
8- (1,1-dimethylethyl) -N-ethyl-N-propyl-1,4-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,
cis-1- (4-chlorophenyl) -2- (1H-1,2,4-triazol-1-yl) cycloheptanol,
cis-4- [3- [4- (1,1-dimethylpropyl) phenyl-2-methylpropyl] -2,6-dimethylmorpholine hydrochloride,
Ethyl - [(4-chlorophenyl) azo] cyanoacetate,
Potassium hydrogen carbonate,
Methane tetrathiol sodium salt,
Methyl 1- (2,3-dihydro-2,2-dimethyl-1H-inden-1-yl) -1H-imidazole-5-carboxylate,
Methyl N- (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) -1,4,5,6-tetrahydro-2-pyrimidinamine,
N- (4-hexylphenyl) -1,4,5,6-tetrahydro-2-pyrimidinamine,
N- (5-chloro-2-methylphenyl) -2-methoxy-N- (2-oxo-3-oxazolidinyl) acetamide,
N- (6-methoxy-3-pyridinyl) cyclopropanecarboxamide,
N- [2,2,2-trichloro-1 - [(chloroacetyl) amino] ethyl] benzamide,
N- [3-chloro-4,5-bis (2-propynyloxy) phenyl) -N'-methoxymanimidamide,
N-formyl-N-hydroxy-DL-alanine sodium salt,
O, O-diethyl- [2- (dipropylamino) -2-oxoethyl] ethylphosphoramidothioate,
O-methyl-S-phenyl-phenylpropylphosphoramidothioat,
S-methyl-1,2,3-benzothiadiazole-7-carbothioate,
spiro [[2H] -1-benzopyran-2,1 '(3'H) -isobenzofuran] -3'-one.

Bactericides

Bronopol, dichlorophene, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, Octhilinone, furan carboxylic acid, oxytetracycline, probenazole, streptomycin, Teclofia lam, copper sulfate and other copper preparations.

Insecticides / acaricides / nematicides

Abamectin, Acephate, Acetamiprid, Acrinathrin, Alanycarb, Aldicarb, Aldoxycarb, Alpha-cypermethrin, Alphamethrin, Amitraz, Avermectin, AZ 60541, Azadirachtin, Azamethiphos, Azinphos A, Azinphos M, Azocyclotin,
Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis, Bacillus thuringiensis, Baculoviruses, Beauveria bassiana, Beauveria tenella, Bendiocarb, Benfuracarb, Bensultap, Benzoximate, Betacyfluthrin, Bifenazate, Bifenthrin, Bioethanomefufenol, Bifenthrin, Bioethanomofufenhrin carboxim, butylpyridaben,
Cadusafos, carbaryl, carbofuran, carbophenothion, carbosulfan, cartap, Chlo ethocarb, chlorethoxyfos, chlorfenapyr, chlorfenvinphos, chlorfluazuron, chlorine mephos, chlorpyrifos, chlorpyrifos M, Chlovaporthrin, cis-resmethrin, Cisper methrin, Clocythrin, cloethocarb, clofentezine, cyanophos, Cycloprene, Cyclo prothrin, cyfluthrin, cyhalothrin, cyhexatin, cypermethrin, cyromazine,
Deltamethrin, Demeton M, Demeton S, Demeton-S-methyl, Diafenthiuron, Diazinon, Dichlorvos, Diflubenzuron, Dimethoat, Dimethylvinphos, Diofenolan, Disulfoton, Docusat-sodium, Dofenapyn,
Eflusilanate, Emamectin, Empenthrin, Endosulfan, Entomopfthora spp., Esfen valerate, Ethiofencarb, Ethion, Ethoprophos, Etofenprox, Etoxazole, Etrimfos,
Fenamiphos, Fenazaquin, Fenbutatin oxide, Fenitrothion, Fenothiocarb, Fenoxacrim, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyrithrin, Fenpyroximate, Fenvalerate, Fipronil, Fluazinam, Fluazuron, Flubrocythrinate, Flucycloxoxuron, Fluutinoxuron, Fluutinoxuron, Fluutinoxuron, Fluutinoxanone, fenprox, furathiocarb,
Granulosis viruses,
Halofenozide, HCH, Heptenophos, Hexaflumuron, Hexythiazox, Hydroprene,
Imidacloprid, isazofos, isofenphos, isoxathion, ivermectin,
Nuclear polyhedron viruses,
Lambda cyhalothrin, lufenuron,
Malathion, Mecarbam, Metaldehyde, Methamidophos, Metharhician anisopliae, Metharhician flavoviride, Methidathione, Methiocarb, Methomyl, Methoxyfenozide, Metolcarb, Metoxadiazone, Mevinphos, Milbemectin, Monocrotophos,
Naled, Nitenpyram, Nithiazine, Novaluron,
Omethoate, oxamyl, oxydemethone M,
Paecilomyces flimosoroseus, Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalone, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos A, Pirimiphos M, Profenofos, Promecarb, Propoxur, Prothiofos, Prothoat, Pyromhrhridosine, Pymmethrofinos, Pymmethrofinos , Pyridathione, Pyrimidifen, Pyri proxyfen,
Quinalphos,
Ribavirin,
Salithion, Sebufos, Silafluofen, Spinosad, Sulfotep, Sulprofos,
Tau fluvalinate, tebufenozide, tebufenpyrad, tebupirimiphos, teflubenzuron, te fluthrin, temephos, temivinphos, terbufos, tetrachlorvinphos, theta-cypermethrin, thiamethoxam, thiapronil, thiatriphos hydrogen, thiocaloxinoxinoxinoxinoxinoxinoxinoxinoxinoxaline, thiapinoxin , Triazophos, triazuron, trichlophenidines, trichlorfon, triflumuron, trimethacarb,
Vamidothion, Vaniliprole, Verticillium lecanii,
YI 5302,
Zeta-cypermethrin, zolaprofos,
(1R-cis) - [5- (phenylmethyl) -3-furanyl] methyl-3 - [(dihydro-2-oxo-3 (2H) - furanylidene) methyl] -2,2-dimethylcyclopropane carboxylate,
(3-phenoxyphenyl) methyl 2,2,3,3-tetramethylcyclopropane decarboxylate,
1 - [(2-chloro-5-thiazolyl) methyl] tetrahydro-3,5-dimethyl-N-nitro-1,3,5-triazine-2 (1H) - imine,
2- (2-chloro-6-fluorophenyl) -4- [4- (1,1-dimethylethyl) phenyl] -4,5-dihydro-oxazole,
2- (acetyloxy) -3-dodecyl-1,4-naphthalenedione,
2-chloro-N - [[[4- (1-phenylethoxy) phenyl] amino] carbonyl] benzamide,
2-chloro-N - [[[4- (2,2-dichloro-1,1-difluoroethoxy) phenyl] amino] carbonyl] benzamide,
3-methylphenyl propyl carbamate,
4- [4- (4-ethoxyphenyl) -4-methylpentyl] -1-fluoro-2-phenoxy-benzene,
4-chloro-2- (1,1-dimethylethyl) -5 - [[2- (2,6-dimethyl-4-phenoxyphenoxy) ethyl] thio] - 3 (2H) -pyridazinone,
4-chloro-2- (2-chloro-2-methylpropyl) -5 - [(6-10d-3-pyridinyl) methoxy] -3 (2H) - pyridazinone,
4-chloro-5 - [(6-chloro-3-pyridinyl) methoxy) -2- (3,4-dichlorophenyl) -3 (2H) pyridazinone
Bacillus thuringiensis strain EG-2348,
Benzoic acid [2-benzoyl-1- (1,1-dimethylethyl) hydrazide,
Butanoic acid 2,2-dimethyl-3- (2,4-dichlorophenyl) -2-oxo-1-oxaspiro [4.5] dec-3-en-4-yl ester,
[3 - [(6-chloro-3-pyridinyl) methyl] -2-thiazolidinylidene] cyanamide,
Dihydro-2- (nitromethylene) -2H-1,3-thiazine-3 (4H) -carboxaldehyde,
Ethyl [2 - [[1,6-dihydro-6-oxo-1- (phenylmethyl) -4-pyridazinyl] oxy] ethyl] carbamate,
N- (3,4,4-trifluoro-1-oxo-3-butenyl) glycine,
N- (4-chlorophenyl) -3- [4- (difluoromethoxy) phenyl] -4,5-dihydro-4-phenyl-1H-pyrazole-1-carboxamide,
N - [(2-chloro-5-thiazolyl) methyl] -N'-methyl-N "-nitro-guanidine,
N-methyl-N '- (1-methyl-2-propenyl) -1,2-hydrazinedicarbothioamide,
N-methyl-N'-2-propenyl-1,2-hydrazinedicarbothioamide,
O, O-Diethyl- [2- (dipropylamino) -2-oxoethyl] ethyl phosphoramidothioate.

A mixture with other known active ingredients, such as herbicides or with Fertilizers and growth regulators are possible.

When used as insecticides, the active compounds according to the invention can also be used in their commercial formulations and be from these formulations use forms in mixture with synergists. Synergists are compounds that increase the effectiveness of the active ingredients without the added synergist itself must be active.

The active ingredient content of the prepared from the commercially available formulations Application forms can vary widely. The drug concentration of the Use forms can be from 0.0000001 to 95% by weight of active ingredient, preferably are between 0.0001 and 1% by weight.

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

When used against hygiene and storage pests, the effect is noticeable fabric through an excellent residual effect on wood and clay as well as through a good alkali stability on limed substrates.

The active compounds according to the invention act not only against plant, hygiene and Pests, but also against the veterinary sector animal parasites (ectoparasites) such as tortoise ticks, leather ticks, mite mites, Running mites, flies (stinging and licking), parasitic fly larvae, lice, Hair lice, featherlings and fleas. These parasites include:

From the order of the Anoplurida z. B. Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.

From the order of the Mallophagida and the subordinates Amblycerina as well Ischnocerina e.g. B. Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Wemeckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp.

From the order Diptera and the subordinates Nematocerina as well Brachycerina e.g. B. Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp.

From the order of the Siphonapterida z. B. Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp.

From the order of the Heteropterida z. B. Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp.  

From the order of the Blattarida z. B. Blatta orientalis, Periplaneta americana, Blattela germanica, Supella spp.

From the subclass of Acaria (Acarida) and the orders of the Meta and Mesostigmata e.g. B. Argas spp., Ornithodorus spp., Otobius spp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp., Raillietia spp., Pneumo nyssus spp., Sternostoma spp., Varroa spp.

From the order of the Actinedida (Prostigmata) and Acaridida (Astigmata) z. B. Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp.

For example, the compounds according to the invention have a good effect against flies (Musca domestica), ticks (Boophilus microplus), cockroaches (Peri planeta americana) and fleas (Ctenocephalides felis) and good development inhibitory effect against fly larvae from Lucilia cuprina and flea eggs from Ctenocephalides felis.

The active compounds of the formula (I) according to the invention are also suitable for combating of arthropods, the farm animals, such as. B. cattle, sheep, goats, Horses, pigs, donkeys, camels, buffaloes, rabbits, chickens, turkeys, ducks, geese, Bees, other pets such as B. dogs, cats, house birds, aquarium fish as well as so-called experimental animals, such as. B. hamsters, guinea pigs, rats and Infest mice. By fighting these arthropods, deaths and Reductions in performance (for meat, milk, wool, skins, eggs, honey, etc.)  can be reduced so that by using the active compounds according to the invention more economical and easier animal husbandry is possible.

The active compounds according to the invention are used in the veterinary sector in in a known manner by enteral administration in the form of, for example, tablets, Capsules, watering, drenching, granules, pastes, boluses, the feed-through process, suppositories, by parenteral administration, such as by injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), implants, through nasal Application, by dermal application in the form of, for example, diving or Bathing (dipping), spraying (spray), pouring (pour-on and spot-on), des Washing, powdering and with the help of active ingredient-containing moldings, such as Collars, ear tags, tail tags, limb straps, halters, Mar marking devices etc.

When used for cattle, poultry, pets etc., you can use the active ingredients in Formula (I) as formulations (for example powders, emulsions, flowable Agents), which contain the active ingredients in an amount of 1 to 80 wt .-%, directly or after 100 to 10,000-fold dilution or use it as a chemical bath use.

It was also found that the compounds of the invention have a high Show insecticidal activity against insects that destroy technical materials.

The following insects may be mentioned by way of example and preferably, but without limitation:
Beetle like
Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Ptilinus pecticornis, Dendrobium pertinex, Ernobius mollis, Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctus planicollis, Lyctus linearesces, Lyctus linearises, Spec spec., Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec., Dinoderus minutus.
Frequent flyers like
Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur.
Termites like
Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus.
Bristle tails like
Lepisma saccharina.

In the present context, technical materials include non-living ones Understand materials, such as preferably plastics, adhesives, glues, papers and cartons, leather, wood, woodworking products and paints.

The one to be protected against insect attack is very particularly preferably Material around wood and wood processing products.

Wood and wood processing products which can be protected by the agent according to the invention or mixtures containing it are to be understood as examples:
Lumber, wooden beams, railway sleepers, bridge parts, jetties, wooden vehicles, boxes, pallets, containers, telephone poles, wooden cladding, wooden windows and doors, plywood, chipboard, carpentry or wooden products that are generally used in house construction or joinery.

The active ingredients can be used as such, in the form of concentrates or in general usual formulations such as powders, granules, solutions, suspensions, emulsions or pastes.  

The formulations mentioned can be prepared in a manner known per se be, e.g. B. by mixing the active ingredients with at least one solution or Diluents, emulsifiers, dispersants and / or binders or fixatives, Water repellants, possibly desiccants and UV stabilizers and added if necessary dyes and pigments and other processing aids.

The insecticidal agents or used to protect wood and wood-based materials Concentrates contain the active ingredient according to the invention in a concentration of 0.0001 to 95% by weight, in particular 0.001 to 60% by weight.

The amount of agents or concentrates used depends on the type and type come from insects and depending on the medium. The optimal amount to use can be determined by test series in the application. In general however, it is sufficient 0.0001 to 20% by weight, preferably 0.001 to 10% by weight, of the active ingredient, based on the material to be protected.

An organic chemical solution serves as the solvent and / or diluent medium or solvent mixture and / or an oily or oily difficult to cure term organic chemical solvent or solvent mixture and / or a polar organic chemical solvent or solvent mixture and / or Water and optionally an emulsifier and / or wetting agent.

The organic chemical solvents used are preferably oily or oily ones Solvents with an evaporation number above 35 and a flash point above 30 ° C, preferably above 45 ° C, used. As such a volatile thing Corresponding mineral oils become serum-insoluble, oily and oily solvents or their aromatic fractions or mineral oil-containing solvent mixtures preferably white spirit, petroleum and / or alkylbenzene used.  

Mineral oils with a boiling range of 170 to 220 ° C are advantageous, test petrol with a boiling range of 170 to 220 ° C, spindle oil with a boiling range from 250 to 350 ° C, petroleum or aromatics with a boiling range from 160 to 280 ° C, Turpentine oil and the like.

In a preferred embodiment, liquid aliphatic hydrocarbons substances with a boiling range of 180 to 210 ° C or high-boiling mixtures of aromatic and aliphatic hydrocarbons with a boiling range of 180 to 220 ° C and / or locker oil and / or monochloronaphthalene, preferably α-mono chloronaphthalene used.

The organic non-volatile oily or oily solvents with a Evaporation rate above 35 and a flash point above 30 ° C, preferably above 45 ° C, can be partially organic or slightly volatile chemical solvents are replaced, provided that the solvent mix also an evaporation number above 35 and a flash point above 30 ° C, preferably above 45 ° C, and that the insecticide fungicide Mixture is soluble or emulsifiable in this solvent mixture.

According to a preferred embodiment, part of the organic chemical Solvent or solvent mixture or an aliphatic polar orga niche chemical solvent or solvent mixture replaced. Preferably come aliphatic containing hydroxyl and / or ester and / or ether groups organic chemical solvents such as glycol ether, ester or the like. to use.

As an organic chemical binder in the present Er finding the known water-dilutable and / or in the used organic chemical solvents soluble or dispersible or emulsifiable Synthetic resins and / or binding drying oils, in particular binders from or containing an acrylic resin, a vinyl resin, e.g. B. polyvinyl acetate, polyester  resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as indene-coumarone resin, silicone resin, drying vegetable and / or drying oils and / or physically drying binders based on a natural and / or synthetic resin used.

The synthetic resin used as a binder can be in the form of an emulsion, dispersion or solution. Bitumen or bitumi can also be used as binders nous substances up to 10 wt .-% can be used. In addition, in itself known dyes, pigments, water repellants, odor correctors and Inhibitors or anticorrosive agents and the like are used.

According to the invention, preference is given to at least one organic chemical binder an alkyd resin or modified alkyd resin and / or a drying vegetable Contain oil in the medium or in the concentrate. Are preferred according to the invention Alkyd resins with an oil content of more than 45% by weight, preferably 50 to 68% by weight.

The binder mentioned can be wholly or partly by a fixation medium (mixture) or a plasticizer (mixture) can be replaced. These additions should len volatilization of the active ingredients and crystallization or precipitators prevent. They preferably replace 0.01 to 30% of the binder (based on 100% of the binder used).

The plasticizers come from the chemical classes of phthalic acid esters such as Dibutyl, dioctyl or benzyl butyl phthalate, phosphoric acid esters such as tributyl phosphate, adipic acid esters such as di- (2-ethylhexyl) adipate, stearates such as butyl stearate or amyl stearate, oleates such as butyl oleate, glycerol ether or higher molecular weight Gly kolether, glycerol ester and p-toluenesulfonic acid ester.  

Fixing agents are chemically based on polyvinyl alkyl ethers such as. B. Polyvinyl methyl ether or ketones such as benzophenone, ethylene benzophenone.

Water is also particularly suitable as a solvent or diluent, optionally mixed with one or more of the above organic chemical solvents or diluents, emulsifiers and dispersants.

A particularly effective wood protection is achieved through industrial impregnation processes, e.g. B. vacuum, double vacuum or printing process.

The ready-to-use agents can, if appropriate, still further insecticides and optionally contain one or more fungicides.

The additional mixing partners are preferably those in WO 94/29 268 Insecticides and fungicides mentioned in question. The ones mentioned in this document Connections are an integral part of this application.

Insecticides, such as chlorpyriphos, phoxime, silafluofin, alphamethrin, cyfluthrin, cypermethrin, deltamethrin, permethrin, imidacloprid, NI-25, flufenoxuron, hexaflumuron, transfluthrin, methoxyphenuronopridif,
as well as fungicides such as epoxyconazole, hexaconazole, azaconazole, propiconazole, tebuconazole, cyproconazole, metconazole, imazalil, dichlorofluoride, tolylfluanid, 3-iodo-2-propynylbutylcarbamate, N-octyl-isothiazolin-3-one and 4,5-dichloro - octylisothiazolin-3-one.

At the same time, the compounds according to the invention can protect against fouling objects, in particular hulls, sieves, nets, structures, Quays and signaling systems, which are connected to sea or brackish water come, be used.  

Overgrowth by sessile oligochaetes, such as lime tube worms and by mussels and species of the group Ledamorpha (barnacles), such as various Lepas and Scalpellum species, or by species from the group Balanomorpha (barnacles), such as Balanus or pollicipes species, increases the frictional resistance of ships and subsequently performs through increased energy consumption and beyond frequent dry dock stays for a significant increase in operating costs.

In addition to the growth by algae, for example Ectocarpus sp. and Ceramium sp., comes in particular the vegetation by sessile Entomostraken groups, which can be summarized under the name Cirripedia (barnacles) their importance.

It has now surprisingly been found that the verbin alone or in combination with other active ingredients, an excellent Have antifouling effect.

By using compounds according to the invention alone or in combination with other active ingredients, can rely on the use of heavy metals such. B. in bis- (trialkyltin) sulfides, tri-n-butyltin laurate, tri-n-butyltin chloride, copper (I) oxide, Triethyltin chloride, tri-n-butyl (2-phenyl-4-chlorophenoxy) tin, tributyltin oxide, Molybdenum disulfide, antimony oxide, polymeric butyl titanate, phenyl (bispyridine) bis mutch chloride, tri-n-butyltin fluoride, manganese ethylene bisthiocarbamate, zinc dimethyl dithiocarbamate, zinc ethylene bisthiocarbamate, zinc and copper salts of 2-pyridine thiol-1-oxide, bisdimethyldithiocarbamoylzinkethylene bisthiocarbamate, zinc oxide, Copper (I) ethylene bisdithiocarbamate, copper thiocyanate, copper naphthenate and tri butyltin halides or the concentration of these compounds be significantly reduced.

The ready-to-use antifouling paints can also be used if necessary Active ingredients, preferably algicides, fungicides, herbicides, molluscicides or others Contain antifouling agents.  

Suitable combination partners for the antifouling agents according to the invention are preferably:
Algicides like
2-tert-butylamino-4-cyclopropylamino-6-methylthio-1,3,5-triazine, dichlorophene, diuron, endothal, fentin acetate, isoproturon, methabenzthiazuron, oxyfluorfen, quinoclamine and terbutryn;
Fungicides like
Benzo [b] thiophenecarboxylic acid cyclohexylamide-S. S-dioxide, dichlofluanid, fluor folpet, 3-iodo-2-propynyl butyl carbamate, tolyl fluanide and azoles such as azaconazole, cyproconazole, epoxyconazole, hexaconazole, metconazole, propi conazole and tebuconazole;
Molluscicides like
Fentin acetate, metaldehyde, methiocarb, niclosamide, thiodicarb and trimethacarb;
or conventional antifouling agents such as
4,5-dichloro-2-octyl-4-isothiazolin-3-one, diiodomethylparatrylsulfone, 2- (N, N -dimethylthiocarbamoylthio) -5-nitrothiazyl, potassium, copper, sodium and zinc salts of 2-pyridinthiol- 1-oxide, pyridine-triphenylborane, tetrabutyldistannoxane, 2,3,5,6-tetrachloro-4- (methylsulfonyl) pyridine, 2,4,5,6-tetrachloroisophthalonitrile, tetramethylthiuram disulfide and 2,4,6-trichlorophenylmaleimide.

The antifouling agents used contain the active ingredients according to the invention compounds according to the invention in a concentration of 0.001 to 50% by weight, in particular from 0.01 to 20% by weight.  

The antifouling agents according to the invention also contain the usual Be components such as B. in Ungerer, Chem. Ind. 1985, 37, 730-732 and Williams, Anti fouling Marine Coatings, Noyes, Park Ridge, 1973.

Antifouling paints contain algicidal, fungicidal, molluscicides and insecticidal active substances according to the invention, in particular binders.

Examples of recognized binders are polyvinyl chloride in a solvent system, chlorinated rubber in a solvent system, acrylic resins in one Solvent system especially in an aqueous system, vinyl chloride / vinyl acetate copolymer systems in the form of aqueous dispersions or in the form of organi solvent systems, butadiene / styrene / acrylonitrile rubbers, drying Oils such as linseed oil, resin esters or modified hard resins in combination with Tar or bitumen, asphalt and epoxy compounds, small amounts of chlorine rubber, chlorinated polypropylene and vinyl resins.

Paints may also contain inorganic pigments, organic Pigments or dyes, which are preferably insoluble in sea water. Further Paints can contain materials, such as rosin, to be controlled To enable release of the active ingredients. The paints can also be soft makers, modifiers influencing the rheological properties, and contain other conventional ingredients. Also in self-polishing antifouling Systems can be the compounds of the invention or those mentioned above Mixtures can be incorporated.

The active ingredients are also suitable for combating animal pests, in particular special of insects, arachnids and mites that live in closed rooms, such as for example apartments, factory buildings, offices, vehicle cabins and the like. occur. You can fight these pests alone or in combination with other active ingredients and adjuvants can be used in household insecticide products.  

They are effective against sensitive and resistant species and against all stages of development. These pests include:
From the order of the Scorpionidea z. B. Buthus occitanus.
From the order of Acarina z. B. Argas persicus, Argas reflexus, Bryobia ssp., Dermanyssus gallinae, Glyciphagus domesticus, Ornithodorus moubat, Rhipice phalus sanguineus, Trombicula alfreddugesi, Neutrombicula autumnalis, Dermato phagoides pteronissimus, Dermatophagoides forinae.
From the order of the Araneae z. B. Aviculariidae, Araneidae.
From the order of the Opiliones z. B. Pseudoscorpiones chelifer, Pseudoscorpiones cheiridium, Opiliones phalangium.
From the order of the Isopoda z. B. Oniscus asellus, Porcellio scaber.
From the order of the Diplopoda z. B. Blaniulus guttulatus, Polydesmus spp.
From the order of the Chilopoda z. B. Geophilus spp.
From the order of the Zygentoma z. B. Ctenolepisma spp., Lepisma saccharina, Lepismodes inquilinus.
From the order of the Blattaria z. B. Blatta orientalies, Blaffella germanica, Blattella asahinai, Leucophaea maderae, Panchlora spp., Parcoblatta spp., Periplaneta australasiae, Periplaneta americana, Periplaneta brunnea, Periplaneta fuliginosa, Supella longipalpa.
From the order of the Saltatoria z. B. Acheta domesticus.
From the order of the Dermaptera z. B. Auricular Forficula.
From the order of the Isoptera z. B. Kalotermes spp., Reticulitermes spp.
From the order of Psocoptera z. B. Lepinatus spp., Liposcelis spp.
From the order of the Coleptera z. B. Anthrenus spp., Attagenus spp., Dermestes spp., Latheticus oryzae, Necrobia spp., Ptinus spp., Rhizopertha dominica, Sitophilus granarius, Sitophilus oryzae, Sitophilus zeamais, Stegobium paniceum.
From the order of the Diptera z. B. Aedes aegypti, Aedes albopictus, Aedes taeniorhynchus, Anopheles spp., Calliphora erythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culex pipiens, Culex tarsalis, Drosophila spp., Fannia canicularis. , Stomoxys calcitrans, Tipula paludosa.
From the order of the Lepidoptera z. B. Achroia grisella, Galleria mellonella, Plodia interpunctella, Tinea cloacella, Tinea pellionella, Tineola bisselliella.
From the order of the Siphonaptera z. B. Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis.
From the order of the Hymenoptera z. B. Camponotus herculeanus, Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis, Paravespula spp., Tetramorium caespitum.
From the order of the Anoplura z. B. Pediculus humanus capitis, Pediculus humanus corporis, Phthirus pubis.
From the order of Heteroptera z. B. Cimex hemipterus, Cimex lectularius, Rhodinus prolixus, Triatoma infestans.

The application in the field of household insecticides is carried out alone or in combination nation with other suitable active ingredients such as phosphoric acid esters, carbamates, Pyrethroids, growth regulators or active substances from other known insects ticide classes.

The application takes place in aerosols, unpressurized sprays, e.g. B. Pump and Atomizer sprays, automatic fog machines, foggers, foams, gels, vaporizers products with evaporator plates made of cellulose or plastic, liquid evaporators, Gel and membrane evaporators, propeller-driven evaporators, energy-free or passive evaporation systems, moth papers, moth bags and Moth angels, as granules or dusts, in lures or bait stations.

The active compounds according to the invention can also be used as defoliants, desiccants, kraut tabs killers and especially used as a weed killer. Weeds in the broadest sense are understood to mean all plants that are found in places grow where they are undesirable. Whether the substances according to the invention as total or Selective herbicides act essentially depends on the amount used.

The active compounds according to the invention can, for. B. used in the following plants:
Dicot weeds of the genera:
Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xan thium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Roripperna, Rorippa, Rorippa , Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum.
Dicotyledon cultures of the genera:
Gossypium, Glycine, Beta, Daucus, Phaseolus, Pi sum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cucurbita.
Monocot weeds of the genera:
Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sor ghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischatenumum, Ischaeaumum , Agrostis, Alopecurus, Apera.
Monocot cultures of the genera:
Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Pineapple, Asparagus, Allium.

The use of the active compounds according to the invention is by no means limited to these Limited genres, but extends in the same way to others Plants.

Depending on the concentration, the compounds are suitable for the total weed control z. B. on industrial and track systems and on paths and squares with and without tree cover. Likewise, the connections to weed beds fighting in permanent crops, e.g. B. forest, ornamental wood, fruit, wine, citrus, nut, Banana, coffee, tea, gum, oil palm, cocoa, berry fruit and hop plant on ornamental and sports turf and pastures and for selective weed beds fighting in annual crops.

The compounds of formula (I) according to the invention are particularly suitable for selective control of monocotyledon and dicotyledon weeds in monocotyledons and dicotyledon cultures both pre-emergence and post-emergence.

The active compounds according to the invention can be used as such or in their formulations also used in a mixture with known herbicides for weed control find, where ready formulations or tank mixes are possible.

Known herbicides are suitable for the mixtures, for example:
Acetochlor, Acifluorfen (-sodium), Aclonifen, Alachlor, Alloxydim (-sodium), Ametryne, Amidochlor, Amidosulfuron, Anilofos, Asulam, Atrazine, Azafenidin, Azimsulfuron, Benazolin (-ethyl), Benfuresate, Bensulfuron (-methyl) Benzobicyclone, Benzofenap, Benzoylprop (-ethyl), Bialaphos, Bifenox, Bispyribac- (-sodium), Bromobutide, Bromofenoxim, Bromoxynil, Butachlor, Butroxydim, Butylate, Cafenstrole, Caloxydim, Carbetamide, Carfentrazone (-ethyl), Chlo methoxy, Chlo methoxy, Chlo methoxy Chloridazon, Chlorimuron (-ethyl), Chloronitrofen, Chlor sulfuron, Chlortoluron, Cinidon (-ethyl), Cinmethylin, Cinosulfuron, Clefoxydim, Clethodim, Clodinafop (-propargyl), Clomazone, Clomeprop, Clopyralid, Clopyra sulfuron (-mor -methyl), cumyluron, cyanazine, cybutryne, cycloate, cyclosulfamuron, cycloxydim, cyhalofop (-butyl), 2,4-D, 2,4-DB, 2,4-DP, desmedipham, dialallate, dicamba, diclofop (-methyl ), Diclosulam, Diethatyl (-ethyl), Difenzoquat, Diflufenican, Diflufenzopyr, Dimefüron, Dimepiperate, D imethachlor, dimethametryn, dimethenamid, dimexyflam, dinitramine, diphenamide, diquat, di thiopyr, diuron, dymron, epropodan, EPTC, esprocarb, ethalfluralin, ethametsulfuron (-methyl), ethofumesate, ethoxyfen, ethoxysulfuron, fenoxysulfuron, fenoxysulfuron, ethoxysulfurone ethyl), fentrazamide, flamprop (-isopropyl), flamprop (-isopropyl-L), flamprop- (-methyl), flazasulfuron, florasulam, fluazifop (-P-butyl), fluazolate, flucarbazone, flufenacet, flumetsulam, flumiclorac (-pentyl ), Flumioxazin, Flumipropyn, Flumet sulam, Fluometuron, Fluorochloridone, Fluoroglycofen (-ethyl), Flupoxam, Fluprop acil, Flurpyrsulfuron (-methyl, -sodium), Flurenol (-butyl), Fluridone, Fluroxypyr- (-mprimeptol) Flurtamone, Fluthiacet (-methyl), Fluthiamide, Fomesafen, Glufosinate (-ammonium), Glyphosate (-isopropylammonium), Halosafen, Haloxyfop- (-ethoxyethyl), Haloxyfop (-P-methyl), Hexazinone, Imazamethabenz (-methyl), Imazamethapyr , Imazamox, Imazapic, Imazapyr, Imazaquin, Imazethapyr, Imazo sulfuron, Iodosulfuron (-methyl , -sodium), Ioxynil, Isopropalin, Isoproturon, Isouron, Isoxaben, Isoxachlortole, Isoxaflutole, Isoxapyrifop, Lactofen, Lenacil, Linuron, MCPA, MCPP, Mefenacet, Mesotrione, Metamitron, Metazachlor, Metobobenzuronon (metabenzthuron) uron Metolachlor, Metosulam, Metoxuron, Metribuzin, Metsulfuron (-methyl), Molinate, Monolinuron, Naproanilide, Naprop amide, Neburon, Nicosulfuron, Norflurazon, Orbencarb, Oryzalin, Oxadiargyl, Oxa diazon, Oxasulfomefone, Paraz, Oxa Sulfuron, Oxaqylfluoronone, Oxa , Pendralin, Pentoxazone, Phenmedipham, Piperophos, Pretilachlor, Primi sulfuron (-methyl), Prometryn, Propachlor, Propanil, Propaquizafop, Propisochlor, Propyzamide, Prosulfocarb, Prosulfuron, Pyraflufen (-ethyl), Pyrazolate, Pyrazethyl) uron , Pyribenzoxim, Pyributicarb, Pyridate, Pyriminobac- (-methyl), Pyrithiobac (-sodium), Quinchlorac, Quinmerac, Quinoclamine, Quizalo fop (-P-ethyl), Quizalofop (-P-tefuryl), Rimsulfuron, Sethoxydim, Simaz ine, Sime tryn, Sulcotrione, Sulfentrazone, Sulfometuron (-methyl), Sulfosate, Sulfosulfuron, Tebutam, Tebuthiuron, Tepraloxydim, Terbuthylazine, Terbutryn, Thenylchlor, Thia fluamide, Thiazopyr, Thidiazimin, Thifensulfalkonoxim, Benzyl , Triallates, triasulfuron, tribenuron (-methyl), triclopyr, tridiphane, trifluralin and triflusulfuron.

The active compounds according to the invention can be used both before and after emergence of the plants are applied. They can also be planted in the soil before sowing be working.

When used as herbicides, the amount of active ingredient used can be in one fluctuate larger range. It essentially depends on the type of ge desired effect. In general, the application rates are between 1 g and 10 kg of active ingredient per hectare of soil, preferably between 5 g and 5 kg per hectare

The Ver according to the invention are suitable in appropriate application rates bindings also to control unwanted microorganisms, such as fungi and bacteria, in crop protection and material protection.

The manufacture and use of the active compounds according to the invention start out the following examples.  

Manufacturing examples

example 1

A mixture of 0.454 g (2 mmol) of 5- (6-methoxy-quinolin-4-yl) tetrazole, 0.362 g (2 mmol) trimethyltin hydroxide and 30 ml of methanol are briefly heated to boiling and again cooled to room temperature and filtered. The filtrate is in a vacuum freed from solvent, the residue triturated with diisopropyl ether and aspirated.

0.75 g (96% of theory) of 5- (6-methoxy-quinolin-4-yl) -2-trimethyl is thus obtained tin tetrazole in the form of a colorless powder with a melting point of 230-233 ° C (Decomposition).

Manufacture of the starting product

A mixture of 5.52 g (0.03 mol) of 4-cyano-6-methoxy-quinoline, 2.54 g (0.039 mol) sodium azide, 5.36 g (0.039 mol) triethylamine hydrochloride and 80 ml Toluene is refluxed for 18 hours. Then you extract that Reaction 2 times with 30 ml of water and bring the combined  Water phases by adding 10 percent hydrochloric acid to pH 5. The failed The product is suctioned off and washed with water.

4.93 g (73% of theory) of 5- (6-methoxy-quinolin-4-yl) -tetrazole in are thus obtained Form of a yellow powder with a melting point of 235 ° C (decomposition).

Example 2

To a mixture of 2.7 g (0.02 mol) of 5- (2-furyl) tetrazole, 1.9 g (0.022 mol) Sodium bicarbonate and 80 ml acetone are added 4 g (0.02 mol) trimethyl tin chloride and the reaction mixture is stirred overnight at room temperature. Then 30 ml of water are added and the organic solvent is removed in vacuo distilled. The product crystallizes on standing; it is suctioned off and with water washed.

This gives 1 g (17% of theory) of 5- (2-furyl) -2-trimethyltin tetrazole in the form a colorless powder with a melting point of 175 ° C.  

Example 3

A mixture of 0.75 g (5 mmol) of 3-acetylbenzonitrile, 1 g (5 mmol) of trimethyl Tin azide and 30 ml of toluene are heated under reflux overnight. Then distilled the solvent is removed in vacuo, the residue is stirred with diethyl ether and sucks off the product after crystallization.

This gives 0.55 g (33% of theory) of 5- (3-acetylphenyl) -2-trimethyltin tetrazole in the form of a colorless powder with a melting point of 139 ° C.  

Analogous to Examples 1 to 3 or according to the general information on the preparation the compounds of the formula (I) given in Table A below receive:

Table A

The logP values were determined in accordance with EEC Directive 79/831 Annex V. A8 by HPLC (gradient method, acetonitrile / 0.1% aqueous phosphoric acid).  

Examples of use Example A Heliothis armigera test

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

To prepare a suitable preparation of active compound, 1 Ge is mixed most of the active ingredient with the specified amount of solvent and the specified amount of emulsifier and dilute the concentrate with water to the desired level concentration.

Soybean shoots (Glycine max) are dipped into the active ingredient preparation desired concentration and treated with caterpillars of the cotton capsule worm (Heliothis armigera) occupied while the leaves are still moist.

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

This test shows at an exemplary drug concentration of 0.1% z. B. the compound of preparation example 13 a kill of 100% according to FIG. 6 Days.  

Example B Heliothis virescens test

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

To prepare a suitable preparation of active compound, 1 Ge is mixed most of the active ingredient with the specified amount of solvent and the specified amount of emulsifier and dilute the concentrate with water to the wanted concentration.

Soybean shoots (Glycine max) are dipped into the active ingredient preparation of the ge desired concentration treated and with the tobacco bud caterpillar Heliothis virescens occupied while the leaves are still moist.

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

This test shows at an exemplary drug concentration of 0.1% z. B. the compound of preparation example 13 a kill of 100% according to FIG. 6 Days.  

Example C Myzus test

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

To prepare a suitable preparation of active compound, 1 Ge is mixed most of the active ingredient with the specified amount of solvent and the specified amount of emulsifier and dilute the concentrate with water to the wanted concentration.

Cabbage leaves (Brassica oleracea), heavily from the peach aphid (Myzus persicae) are infested, by dipping into the active ingredient preparation of the desired Concentration treated.

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

In this test, at an exemplary active ingredient concentration of 0.1%, e.g. B. the compounds of preparation examples 1, 7, 8, 10, 11 and 14 kill from 100% after 6 days.  

Example D Phaedon larval test

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

To prepare a suitable preparation of active compound, 1 Ge is mixed most of the active ingredient with the specified amount of solvent and the specified amount of emulsifier and dilute the concentrate with water to the wanted concentration.

Cabbage leaves (Brassica oleracea) are dipped into the active ingredient preparation the desired concentration and treated with larvae of the horseradish beetle (Phaedon cochleariae) occupied 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 are released were killed.

In this test, at an exemplary active ingredient concentration of 0.1%, e.g. B. the compounds of Preparation Examples 1, 6, 7, 8, 10, 11, 13, 14 and 30 a 100% kill after 7 days.  

Example E Plutella test

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

To prepare a suitable preparation of active compound, 1 Ge is mixed most of the active ingredient with the specified amount of solvent and the specified amount of emulsifier and dilute the concentrate with water to the wanted concentration.

Cabbage leaves (Brassica oleracea) are dipped into the active ingredient preparation the desired concentration and treated with caterpillars (Plutella maculipennis) as long as the leaves are still moist.

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

This test shows at an exemplary drug concentration of 0.1% z. B. the compound of preparation example 13 a kill of 100% according to FIG. 6 Days.  

Example F Plutella test / resistant strain

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

To prepare a suitable preparation of active compound, 1 Ge is mixed most of the active ingredient with the specified amounts of solvent and emulsifier and dilute the concentrate to the desired level with water containing emulsifier Concentration.

Cabbage leaves (Brassica oleracea) are dipped into the active ingredient preparation the desired concentration and treated with caterpillars of the resistant strain the cabbage cockroach (Plutella xylostella) is occupied while the leaves are still moist.

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

This test shows at an exemplary drug concentration of 0.1% z. B. the compound of preparation example 13 a kill of 100% according to FIG. 6 Days.  

Example G Spodoptera exigua test

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

To prepare a suitable preparation of active compound, 1 Ge is mixed most of the active ingredient with the specified amounts of solvent and emulsifier and dilute the concentrate with water containing emulsifier to the desired level Concentration.

Cabbage leaves (Brassica oleracea) are dipped into the active ingredient preparation of the desired concentration and treated with caterpillars of the army worm (Spodoptera exigua) occupied while the leaves are still moist.

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

This test shows at an exemplary drug concentration of 0.1% z. B. the compound of preparation example 13 a kill of 100% according to FIG. 6 Days.  

Example H Spodoptera frugiperda test

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

To prepare a suitable preparation of active compound, 1 Ge is mixed most of the active ingredient with the specified amounts of solvent and emulsifier and dilute the concentrate with water containing emulsifier to the desired level Concentration.

Cabbage leaves (Brassica oleracea) are dipped into the active ingredient preparation of the desired concentration and treated with caterpillars of the army worm (Spodoptera frugiperda) occupied while the leaves are still moist.

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

In this test, at an exemplary active ingredient concentration of 0.1%, e.g. B. the compounds of Preparation Examples 1, 6, 7, 8, 10, 11, 13, 14 and 30 a 100% kill after 7 days.  

Example I Tetranychus test (OP-resistant / immersion treatment)

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

To prepare a suitable preparation of active compound, 1 Ge is mixed most of the active ingredient with the specified amounts of solvent and emulsifier and dilute the concentrate with water containing emulsifier to the desired level Concentration.

Bean plants (Phaseolus vulgaris), strongly of all stages of the common Spider mite (Tetranychus urticae) are infested in an active ingredient preparation the desired concentration.

After the desired time, the effect is determined in%. 100% means that all spider mites have been killed; 0% means that there are no spider mites were killed.

In this test, at an exemplary active ingredient concentration of 0.1%, e.g. B. the compounds of Preparation Examples 1, 7, 8, 10, 11, 13 and 14 a 100% kill after 7 days.  

Example J Pre-emergence test

Solvent: 5 parts by weight of acetone
Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To prepare a suitable preparation of active compound, 1 Ge is mixed most of the active ingredient with the specified amount of solvent, gives the specified Amount of emulsifier and dilute the concentrate with water to the desired level Concentration.

Seeds of the test plants are sown in normal soil. After 24 hours sprayed the soil with the active ingredient preparation, so that the desired one Active ingredient quantities are applied per unit area. The concentration of Spray liquor is chosen so that the desired in 1000 l of water / ha Active ingredient quantities are applied.

After three weeks, the degree of damage to the plants is rated in% damage compared to the development of the untreated control. It means:
0% = no effect (like untreated control),
100% = total annihilation.

In this test, for example, the compounds of Preparation Examples 1 show 6, 10, 11, 12, 13 and 14 with good tolerance to culture plants, such as B. corn or sugar beet, strong action against weeds.  

Example K Post emergence test

Solvent: 5 parts by weight of acetone
Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To prepare a suitable preparation of active compound, 1 Ge is mixed most of the active ingredient with the specified amount of solvent, gives the specified Amount of emulsifier and dilute the concentrate with water to the desired level Concentration.

With the active ingredient preparation, test plants are sprayed, which have a height of 5 to 15 cm so that the desired amounts of active ingredient per unit area be applied. The concentration of the spray liquor is chosen so that in 1000 l water / ha the desired amounts of active ingredient are applied.

After three weeks, the degree of damage to the plants is rated in% damage compared to the development of the untreated control.

It means:
0% = no effect (like untreated control),
100% = total annihilation.

In this test, for example, the compounds of Preparation Examples 1 show 6, 10, 11, 12, 13, 14 and 30 strong activity against weeds.  

Example L Test with flies (Musca domestica)

Test animals: adult Musca domestica, Reichwald strain (OP, SP, carbamate-resistant
Solvent: dimethyl sulfoxide

20 mg of active ingredient are dissolved in 1 ml of dimethyl sulfoxide; lower concentrations are made by dilution with Dest H ₂ O.

2 ml of this active ingredient preparation are placed on filter paper dishes (ϕ 9.5 cm) pipetted, which are in Petri dishes of appropriate size. After drying of the filter disks, 25 test animals are transferred to the Petri dish and covered.

After 1, 3, 5, 24 and 48 hours, the effectiveness of the drug preparation determined. 100% means that all flies have been killed; 0% means that no flies were killed.

In this test, at an exemplary active ingredient concentration of 100 ppm e.g. B. the compounds according to Preparation Examples 1, 3, 4, 5, 6, 7, 8, 9, 10, 11, 14, 15, 16, 17, 18, 19, 20, 21, 22 and 23 kill 100%.  

Example M Test with Boophilus microplus resistant / SP-resistant Parkhurst strain

Test animals: adult sucked females
Solvent: dimethyl sulfoxide

20 mg of active ingredient are dissolved in 1 ml of dimethyl sulfoxide, lower concentration NENs are made by dilution with the same solvent.

The test is carried out in 5-fold determination. 1 µl of the solutions is added to the Abdomen injected, the animals transferred into bowls and in an air-conditioned room kept. The effect is determined by the inhibition of egg laying. Here means 100% that no tick has laid.

In this test, an active substance concentration of 20 µg was used as an example per animal B. the compounds according to Preparation Examples 1, 3, 4, 5, 6, 7, 8, 9, 10, 11, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 28 and 29 kill 100%.  

Example N Cockroach test

Test animals: Periplaneta americana
Solvent: dimethyl sulfoxide

20 mg of active ingredient are dissolved in 1 ml of dimethyl sulfoxide, lower concentrations are produced by dilution with Dest H ₂ O.

4 test animals are immersed in the drug preparation to be tested for 1 minute. To Transfer to plastic cups and 7 days storage in an air-conditioned Room the degree of kill is determined.

100% means that all cockroaches have been killed; 0% means that none Cockroaches were killed.

In this test, at an exemplary active ingredient concentration of 100 ppm e.g. B. the compounds according to the preparation examples 4, 6, 8, 10, 14, 15th and 17 100% kill and according to Preparation Examples 1, 5, 9 and 18 a kill rate of 75%.  

Example O Cockroach test

Test animals: Periplaneta americana
Solvent: dimethyl sulfoxide

20 mg of active ingredient are dissolved in 1 ml of dimethyl sulfoxide, lower concentrations are produced by dilution with Dest H ₂ O.

5 ml of this active ingredient preparation are pipetted onto baking wafers (∅ 9.5 cm) are in appropriate sized petri dishes. After the baking wafers have dried 4 test animals are transferred and covered.

After 7 days of storage in an air-conditioned room, the degree of killing becomes certainly.

100% means that all cockroaches have been killed; 0% means that none Cockroaches were killed.

In this test, at an exemplary active ingredient concentration of 100 ppm e.g. B. the compounds according to Preparation Examples 1, 6, 7, 8, 9, 11, 18 and 22 a destruction of 100% and according to the production examples 10, 15, 16, 17, 19, 20 and 23 a 75% kill.  

Example P Test with cat fleas / ora 04411 00070 552 001000280000000200012000285910430000040 0002019923317 00004 04292le recording

Test animals: adults of Ctenocephalides felis
Solvent: dimethyl sulfoxide (DMSO)

For the purpose of producing a suitable formulation, 20 mg of active ingredient are used 1 ml of DMSO a suitable drug solution. 15 µl of this formulation are added to 3 ml of citrated bovine blood and stirred.

10 sober adult fleas (Ctenocephalides felis, strain "Georgi") are in one Chamber (ϕ 3.2 cm) inserted, which is closed at the top and bottom with gauze. On the Chamber is placed a metal cylinder, the underside with parafilm ver is closed. The cylinder contains the 3 ml blood active ingredient formulation, which the Fleas can be absorbed through the parafilm membrane. During the blood is heated to 37 ° C, a temperature of 25 ° C set. Controls are made with the same volume of DMSO with no addition a compound mixed. Triple determinations are carried out.

After 28 hours, the mortality is determined in% (= dead fleas).

In this test, at an exemplary active ingredient concentration of 100 ppm e.g. B. the compounds according to Preparation Examples 1, 5, 7, 10, 15, 16, 17, 19 and 21 a kill of 100% and according to production examples 4, 6, 8, 9, 11, 18, 20, 22 and 23 a 75% kill.  

Example Q Blowfly larva test / development-inhibiting effect

Test animals: Lucilia cuprina larvae
Solvent: dimethyl sulfoxide

20 mg of active ingredient are dissolved in 1 ml of dimethyl sulfoxide, lower concentrations are produced by dilution with Dest H ₂ O.

About 20 Lucilia cuprina larvae are placed in a test tube that contains approx. 1 cm ³ horse meat and 0.5 ml of the active ingredient preparation to be tested. The effectiveness of the active substance preparation is determined after 24 and 48 hours. The test tubes are transferred to beakers with a sand-covered bottom. After a further 2 days, the test tubes are removed and the dolls are counted.

The effect of the drug preparation is based on the number of flies hatched assessed after 1.5 times the development time of an untreated control. Here means 100% that no flies hatched; 0% means that all flies hatched normally.

In this test, z. B. the connection according to preparation example 3 an exemplary active ingredient concentration of 100 ppm, a degree of killing of 100%.

In this test, at an exemplary active ingredient concentration of 100 ppm e.g. B. the compounds according to Preparation Examples 1, 3, 4, 5, 6, 7, 8, 9, 10, 11, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23 and 29 an anti-development 100% effect.  

Example R Test with cat fleas / development inhibitory effect

Test animals: Ctenocephalides felis (all stages: eggs, larvae, pupae and adults)
Solvent: dimethyl sulfoxide

20 mg of active ingredient are dissolved in 1 ml of dimethyl sulfoxide, lower concentrations are produced by dilution with Dest H ₂ O.

200 µl of this preparation of active ingredient are added to 1.8 g of rearing medium (blood meal dium: 125 parts sea sand, 20 parts rat feed, 3 parts blood meal, 2 parts dry yeast) in disposable tubes (ϕ 2.0 cm), mixed homogeneously and overnight dried. A spatula tip of sieved flea eggs (from artificial infected cats).

The effectiveness of the drug preparation is up to 1.5 times the development time of the control approach determined every 2 days by moving the approaches to development stages of fleas are examined.

The criterion for the in vitro effect of a substance is the inhibition of the flea development, or a development standstill before the adult stage. Here means 100% that no adult fleas developed; 0% means that adult fleas have hatched.

In this test, at an exemplary active ingredient concentration of 100 ppm e.g. B. the compounds according to Preparation Examples 1, 3, 4, 5, 6, 7, 8, 9, 10, 11, 14, 15, 16, 17, 18, 19, 20, 21, 22 and 23 an anti-development 100% effect.

Claims (6)

1. Use of compounds of the formula (I)
in which
R ^{1 represents} alkyl, optionally substituted phenyl or optionally substituted hetaryl and
R ^{2 represents} alkyl, optionally substituted cycloalkyl or optionally substituted phenyl,
for controlling animal pests and as herbicides. 2. Compounds of the formula (Ia)
in which
R represents phenyl substituted by halogen, nitro, cyano, hydroxy, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy, haloalkylthio, alkylcarbonyl, phenyl, phenoxy, phenylthio and pyrimidinyloxy, where phenyl, phenoxy, phenylthio or pyrimidinyloxy can each be substituted by Halogen, nitro, cyano, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy, haloalkylthio, phenoxy optionally substituted by halogen, nitro, cyano, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy, haloalkylthio, with the proviso that compounds with
excluded are;
and compounds of the formula (Ib)
in which
R ^{2 represents} alkyl, optionally substituted cycloalkyl or optionally substituted phenyl,
Hetaryl represents 5- or 6-membered, optionally benzo-fused hetaryl, having 1 to 4 identical or different heteroatoms, such as N, S or O atoms, including possible N-oxides, optionally single to triple, identical or different by halogen , Nitro, cyano, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ -Halogenalkylthio substituted, with the proviso that the compound with R ² = n-butyl and
is excluded. 3. Agents for controlling animal pests and herbicides, labeled by containing at least one compound of the formula (I) according to Claim 1. 4. Process for controlling animal pests and herbicides, since characterized in that compounds of formula (I) according to An saying 1 affects pests and / or their habitat. 5. Process for the preparation of pesticides, thereby ge indicates that compounds of formula (I) according to claim 1 with Extenders and / or surfactants mixed. 6. Use of compounds of formula (I) according to claim 1 for Manufacture of pesticides.