DE4433857A1 - New 1-(cyano- or amino- alkyl)-di:halo-imidazole derivs. - Google Patents

Abstract

N-substd. imidazole derivs. of formula (I) are new. R1 = H or opt. substd. alkyl, alkoxy or aryl; R2 = CN or opt. substd. amino; R = CN, CX1X2X3 or COX4; X1-X3, X, Y = halogen; X4 = opt. substd. amino, alkyl, alkoxy or alkylthio.

Description

The invention relates to new N-substituted imidazoles, a process for their preparation position and their use as herbicides and pesticides.

It is known that certain imidazoles, such as N-chlorobutyloxy methyl-2,4,5-trichlorimidazole insecticidal properties (JP 62 93279) or how 2,4,5-Trichlorimidazole herbicidal properties (DOS 2 005 325) have.

The effectiveness of these previously known compounds is, however, in particular low application rates and concentrations not always in all applications areas completely satisfactory.

New N-substituted imidazoles of the formula (I) have now been found

in which
R¹ represents hydrogen or represents optionally substituted alkyl, alkoxy or aryl,
R² stands for cyano or for optionally substituted amino,
Y¹ and Y² are independently halogen,
X¹, X² and X³ are independently halogen or together are nitrogen or
X¹ and X² together represent oxygen and
X³ represents in each case optionally substituted amino, alkyl, alkoxy or alkylthio.

The compounds of formula (I) may vary depending on the substituents are present as stereoisomer mixtures. They can be both in the form of their Diastereomer mixtures as well as pure diastereomers or enantiomers are present and used.

It was also found that the new N-substituted imidazoles Formula (I) is obtained if 1H-imidazoles of the formula (II)

in which
X¹, X², X³, Y¹ and Y² have the meaning given above,
with compounds of the formula (III)

in which
M stands for a suitable leaving group, and
R¹ and R² have the meaning given above
if appropriate in the presence of a diluent and if appropriate in the presence of a reaction auxiliary.

Finally, it was found that the new substituted imidazoles of the formula (I) have good effectiveness as herbicides and pesticides.

Surprisingly, the new substituted imidazoles according to the invention show the formula (I) has a considerable herbicidal activity against problem weeds t and at the same time a comparably good tolerance to important ones Cultivated plants and a significantly better effectiveness compared to animal Pests as the most structurally similar known compounds.

The N-substituted imidazoles according to the invention are general by the formula (I) my defined.

Preferred substituents or ranges in the above and below he radicals mentioned formulas are explained below.

R¹ preferably represents hydrogen, in each case optionally substituted by halogen C₁-C₈-alkyl or C₁-C₈-alkoxy or for optionally mono- or polysubstituted, identically or differently substituted, phenyl, the following being suitable as substituents:
Halogen, cyano, nitro, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkyl, C₁-C₆-haloalkoxy, C₁- C₆-haloalkylthio, C₁-C₆-haloalkylsulfinyl, C₁-C₆-haloalkylsulfonyl each having 1 to 13 identical or different halogen atoms, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-alkoxy-C₁-C₆-alkoxy, C₁ -C₆-alkylcarbonyl, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkoximino-C₁-C₆-alkyl, optionally one or more times, identically or differently by halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl having 1 to 10 of the same or different halogen atoms substituted doubly linked C₁-C₅-dioxyalkylene or optionally singly or multiply identical or different by halogen, C₁-C₆-alkyl or C₁-C₆-haloalkyl with 1 to 13 identical or different halogen atoms substituted phenyl.

R² preferably represents cyano or the rest

wherein
R³ represents hydrogen for C₁-C₈-alkyl, C₂-C₈-alkenyl, C₃-C₈-cycloalkyl or for optionally substituted one or more times, identically or differently, the substituted phenyl, the phenyl substituents mentioned in R¹ being suitable as phenyl substituents, and
R⁴ for formyl, CONH (C₁-C₈-alkyl), CON (C₁-C₈-alkyl) ₂, CSNH (C₁-C₈-alkyl), CSN (C₁-C₈-alkyl) ₂, SO₂NH (C₁-C₈-alkyl) , SO₂N (C₁-C₈-alkyl) ₂, C₃-C₈-cycloalkyl, C₃-C₈-cycloalkylcarbonyl, C₃-C₈-cycloalkyloxycarbonyl, C₁-C₈-alkylcarbonyl, C₃-C₈-alkenyl carbonyl, C₁-C₈-alkoxycarbonyl, C₃- C₈-alkenyloxycarbonyl, C₁-C₈- alkylthiocarbonyl, C₁-C₈-alkoxythiocarbonyl, C₁-C₈-alkylthio-thio carbonyl, C₁-C₈-alkylsulfonyl, each in the phenyl radical mono- or polysubstituted, identically or differently substituted, phenyl-C₁-C₈-alkyl, Phenyl-C₁-C₈-alkylcarbonyl, phenyl-C₁-C₈-alkyloxycarbonyl, phenyl, phenylcarbonyl, phenyloxycarbonyl or phenylsulfonyl, where the phenyl substituents mentioned in R¹ are also suitable as phenyl substituents, furthermore optionally substituted by halogen-substituted pyridyloxycarbonyl, pyrimidinyloxy carbonyl or thienyloxycarbonyl or
R³ and R⁴ together represent C₂-C₆-alkanediylcarbonyl or C₂-C₆-alkane diyloxycarbonyl.
Y¹ and Y² are independently fluorine, chlorine, bromine or iodine.
X¹, X² and X³ are preferably independently of one another fluorine, chlorine, bromine or iodine or together nitrogen or
X¹ and X² together represent oxygen and
X³ for in each case optionally substituted by halogen C₁-C₈-alkyl, C₁-C₈-alkoxy or C₁-C₈-alkylthio or for amino which is monosubstituted or disubstituted identically or differently, the following being suitable as substituents:
C₁-C₈-alkyl, C₁-C₈-alkoxy, C₂-C₈-alkenyl, C₃-C₁₀-cycloalkyl, C₁-C₈-haloalkyl, C₁-C₈-haloalkoxy, C₂-C₈-haloalkenyl, C₃-C₁₀-halo gencycloalkyl, each optionally single to triple the same or different by the phenyl radicals mentioned at R¹ substituted phenyl, phenyl-C₁-C₆-alkyl, double-linked, ring-closed, optionally interrupted by at least one heteroatom from the series nitrogen, oxygen, sulfur C₂-C₉-alkanediyl .
R¹ particularly preferably represents hydrogen, in each case optionally substituted by halogen C₁-C₆-alkyl or C₁-C₆-alkoxy or for optionally monosubstituted to trisubstituted by identical or different substituents, the following being suitable as substituents:
Fluorine, chlorine, bromine, iodine, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylsulfinyl, C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkyl, C₁ -C₄-haloalkoxy, C₁-C₄-haloalkylthio, C₁-C₄-haloalkyl sulfinyl, C₁-C₄-haloalkylsulfonyl each having 1 to 9 identical or different halogen atoms, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkoxy - C₁-C₄-alkoxy, C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkoximino-C₁-C₄-alkyl, optionally single to five times, the same or different by halogen, C₁-C₄-alkyl, C₁ -C₄-Haloalkyl with 1 to 8 identical or different halogen atoms substituted doubly linked C₁-C₄-dioxyalkylene or optionally up to three times the same or different by halogen, C₁-C₄-alkyl or C₁-C₄-halo genalkyl with 1 to 9 identical or different Halogen atoms substituted phenyl, where halogen represents fluorine, chlorine, bromine.
R² particularly preferably represents cyano or the rest

wherein
R³ represents hydrogen, C₁-C₄-alkyl, C₂-C₆-alkenyl, C₃-C₇-cycloalkyl or phenyl which may be monosubstituted to trisubstituted by identical or different substituents, the phenyl substituents mentioned in R¹ being suitable and
R⁴ for formyl, CONH (C₁-C₆-alkyl), CON (C₁-C₆-alkyl) ₂, CSNH (C₁-C₆-alkyl), CSN (C₁-C₆-alkyl) ₂, SO₂NH (C₁-C₆-alkyl) , SO₂N (C₁-C₆-alkyl) ₂, C₃-C₇-cycloalkyl, C₃-C₇-cycloalkylcarbonyl, C₃-C₇-cycloalkyloxycarbonyl, C₁-C₆-alkylcarbonyl, C₃-C₆-alkenyl carbonyl, C₁-C₆-alkoxycarbonyl, C₃- C₆-alkenyloxycarbonyl, C₁-C₆- alkylthiocarbonyl, C₁-C₆-alkoxythiocarbonyl, C₁-C₆-alkylthio-thio carbonyl, C₁-C₆-alkylsulfonyl, each in the phenyl radical mono- or polysubstituted, identically or differently substituted, phenyl-C₁-C₆-alkyl, Phenyl-C₁-C₆-alkylcarbonyl, phenyl-C₁-C₆-alkyloxycarbonyl, phenyl, phenylcarbonyl, phenyloxycarbonyl or phenylsulfonyl, where the phenyl substituents mentioned in R¹ are also suitable as phenyl substituents, furthermore optionally substituted by halogen-substituted pyridyloxycarbonyl, pyrimidinyloxy carbonyl or thienyloxycarbonyl or
R³ and R⁴ together represent C₂-C₅-alkanediylcarbonyl or C₂-C₅-alkane diyloxycarbonyl.
Y¹ and Y² independently of one another are particularly preferably fluorine, chlorine, bromine or iodine.
X¹, X² and X³ are particularly preferably independently of one another fluorine, chlorine or bromine or together for nitrogen or
X¹ and X² together represent oxygen and
X³ for in each case optionally substituted by halogen C₁-C₇-alkyl, C₁-C₇-alkoxy or C₁-C₇-alkylthio or for amino which is monosubstituted or disubstituted identically or differently, the following being suitable as substituents:
C₁-C₇-alkyl, C₁-C₇-alkoxy, C₂-C₇-alkenyl, C₃-C₈-cycloalkyl, C₁-C₇-haloalkyl, C₁-C₇-haloalkoxy, C₃-C₇-haloalkenyl, C₃-C₁₀-halo gencycloalkyl, each optionally single to triple the same or different by the phenyl radicals mentioned at R¹ substituted phenyl, phenyl-C₁-C₄-alkyl, double-linked, ring-closed, optionally interrupted by at least one heteroatom from the series nitrogen, oxygen, sulfur C₂-C₆-alkanediyl .
R¹ particularly preferably represents hydrogen, in each case optionally substituted by halogen C₁-C₄-alkyl or C₁-C₄-alkoxy or for optionally monosubstituted to trisubstituted by identical or different substituents, the following being suitable as substituents:
Fluorine, chlorine, bromine, iodine, cyano, nitro, C₁-C₃-alkyl, C₁-C₃-alkoxy, C₁-C₃-alkylthio, C₁-C₃-alkylsulfinyl, C₁-C₃-alkylsulfonyl, C₁-C₃-halogenoalkyl, C₁ -C₃-haloalkoxy, C₁-C₃-haloalkylthio, C₁-C₃-haloalkyl sulfinyl, C₁-C₃-haloalkylsulfonyl each having 1 to 7 identical or different halogen atoms, C₁-C₃-alkoxy-C₁-C₃-alkyl, C₁-C₃-alkoxy - C₁-C₃-alkoxy, C₁-C₃-alkylcarbonyl, C₁-C₃-alkoxycarbonyl, C₁-C₃-alkoximino-C₁-C₃-alkyl, optionally single to five times, the same or different by halogen, C₁-C₃-alkyl, C₁ -C₃-haloalkyl with 1 to 6 identical or different halogen atoms substituted doubly linked C₁-C₃-dioxyalkylene or optionally single to twice the same or different by halogen, C₁-C₃-alkyl or C₁-C₃-halo genalkyl with 1 to 7 identical or different Halogen atoms substituted phenyl, where halogen represents fluorine, chlorine, bromine.
R² very particularly preferably represents cyano or the rest

wherein
R³ is hydrogen, C₁-C₄-alkyl, C₂-C₄-alkenyl, C₃-C₆-cycloalkyl or phenyl which is mono- or disubstituted, identically or differently substituted, phenyl substituents mentioned in R¹ being suitable and
R⁴ for formyl, CONH (C₁-C₄-alkyl), CON (C₁-C₄-alkyl) ₂, CSNH (C₁-C₄-alkyl), CSN (C₁-C₄-alkyl) ₂, SO₂NH (C₁-C₄-alkyl) , SO₂N (C₁-C₄-alkyl) ₂, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkylcarbonyl, C₃-C₆-cycloalkyloxycarbonyl, C₁-C₄-alkylcarbonyl, C₃-C₄-alkenyl carbonyl, C₁-C₄-alkoxycarbonyl, C₃- C₄-alkenyloxycarbonyl, C₁-C₄- alkylthiocarbonyl, C₁-C₄-alkoxythiocarbonyl, C₁-C₄-alkylthio-thio carbonyl, C₁-C₄-alkylsulfonyl, each in the phenyl radical mono- or disubstituted, identically or differently substituted phenyl-C₁-C₄-alkyl, Phenyl-C₁-C₄-alkylcarbonyl, phenyl-C₁-C₄-alkyloxycarbonyl, phenyl, phenylcarbonyl, phenyloxycarbonyl or phenylsulfonyl, where the phenyl substituents mentioned in R¹ are also suitable as phenyl substituents, furthermore optionally substituted by halogen-substituted pyridyloxycarbonyl, pyrimidinyloxy carbonyl or thienyloxycarbonyl or
R³ and R⁴ together represent C₂-C₄-alkanediylcarbonyl or C₂-C₄-alkane diyloxycarbonyl.
Y¹ and Y² independently of one another very particularly preferably represent fluorine, chlorine, bromine or iodine.
X¹, X² and X³ very particularly preferably stand independently of one another for fluorine or chlorine or together for nitrogen or
X¹ and X² together represent oxygen and
X³ for in each case optionally substituted by halogen C₁-C₆-alkyl, C₁-C₆-alkoxy or C₁-C₆-alkylthio or for amino which is monosubstituted or disubstituted identically or differently, the following being suitable as substituents:
C₁-C₆-alkyl, C₁-C₆-alkoxy, C₂-C₆-alkenyl, C₃-C₇-cycloalkyl, C₁-C₆-haloalkyl, C₁-C₆-haloalkoxy, C₂-C₆-haloalkenyl, C₃-C₆-halo gencycloalkyl, each optionally single to triple the same or different by the phenyl radicals mentioned at R¹ substituted phenyl, phenyl-C₁-C₃-alkyl, double-linked, ring-closed, optionally interrupted by at least one heteroatom from the series nitrogen, oxygen, sulfur C₂-C₅-alkanediyl .

In particular, besides those mentioned in the production examples Compounds called the following N-substituted imidazoles of formula (I)

The following abbreviations are used in the table:
Me = methyl, Et = ethyl, Pr = propyl, Bu = butyl, Hex = hexyl, Ph = phenyl. CyHex = cyclohexyl

Table 1

Table 2

In Table 2, the meanings of R¹, R², X¹, X² and X³ are each listed as in Table 1 and Y¹ and Y² each represent bromine.

Table 3

In Table 3, the meanings of R¹, R², X¹, X² and X³ are each listed as in Table 1 and Y¹ and Y² each represent fluorine.

Table 4

In Table 4, the meanings of R¹, R², X¹, X² and X³ are each listed as in Table 1 and Y¹ is chlorine and Y² is fluorine.

Table 5

In Table 5, the meanings of R¹, R², X¹, X² and X³ are each listed as in Table 1 and Y¹ is fluorine and Y² is chlorine.  

Table 6

In Table 6, the meanings of R¹, R², X¹, X² and X³ are each listed as in Table 1 and Y¹ is chlorine and Y² is bromine.

Table 7

In Table 7, the meanings of R¹, R², X¹, X² and X³ are each listed as in Table 1 and Y¹ is bromine and Y² is chlorine.

Table 8

In Table 8, the meanings of R¹, R², X¹, X² and X³ are each listed as in Table 1 and Y¹ is fluorine and Y² is bromine.

Table 9

In Table 9, the meanings of R¹, R², X¹, X² and X³ are each listed as in Table 1 and Y¹ is bromine and Y² is fluorine.

For example, 2-N-t-butyl-aminocarbonyl-4,5-dichloroimidazole and N-chloromethyl-N-methyl-carbamide acid ethyl ester as starting materials, so can the course of the reaction of the method according to the invention by the following Represent formula scheme:

To carry out the process according to the invention as starting materials required heterocycles are generally defined by the formula (II). In this Formula (II) Y¹, Y², X¹, X² and X³ preferably represent those radicals which already in connection with the description of the Ver Bonds of formula (I) have been mentioned as preferred for these substituents.

The 1H-imidazoles of the formula (II) are known and / or obtainable in analogy to known methods (DE-OS 29 51 203, DE-OS 31 18 146, DE-OS 26 46 142, DE-OS 26 46 144, DE-OS 26 46 143, DE-OS 26 24 759, DE-OS 26 34 053, DE-OS 31 04 759, DE-OS 29 19 821).

Those used as starting materials for carrying out the process according to the invention required compounds are generally defined by the formula (III). In of this formula (III), R¹ and R² preferably represent those radicals which already exist in connection with the description of the substances of the invention Formula (I) were mentioned as preferred for these substituents.

M stands for a leaving radical customary in alkylating agents, preferably for Halogen, arylsulfonic acid esters, aralkylsulfonic acid esters, alkylsulfonic acid esters, Alkylcarbonyloxy or arylcarbonyloxy, particularly preferably for chlorine, bromine, Iodine, C₁-C₈ alkyl sulfonic acid ester, tolyl sulfonic acid ester, phenyl sulfonic acid ester, C₁-C₈ alkylcarbonyloxy, or benzoyloxy and particularly preferably for chlorine, Bromine, C₁-C₂-alkylsulfonic acid esters, phenylsulfonic acid esters, tolylsulfonic acid esters, C₁-C₃ alkylcarbonyloxy or benzoyloxy.  

The compounds of the formula (III) are known or can be obtained in analogy to known methods [cf. e.g. B. DE 20 40 175; DE 21 19 518; Synthesis 1973, 703; Zh. Obshch. Khim. 56, 1429 (1986)].

The process according to the invention is preferably carried out in the presence of a diluent carried out.

As a diluent for carrying out the method according to the invention inert organic solvents are suitable. These include in particular aliphatic, alicyclic or aromatic, optionally halogenated carbons Hydrogen, such as gasoline, benzene, toluene, xylene, chlorobenzene, Dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform or Carbon tetrachloride, ethers, such as diethyl ether, diisopropyl ether, dioxane, Tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones like Acetone, butanone or methyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile or benzonitrile; Amides, such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; Esters such as methyl acetate or ethyl acetate or bases such as pyridine or organic acids such as formic acid or acetic acid.

The process according to the invention is preferably carried out in the presence of a suitable reaction auxiliary. As such, all the usual ones come inorganic or organic bases in question. These include, for example Alkaline earth metal or alkali metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or hydrogen carbonates, such as sodium hydride, sodium amide, lithium diethylamide, sodium methylate, sodium ethylate, potassium tert-butoxide, Sodium hydroxide, potassium hydroxide, ammonium hydroxide, sodium acetate, Potassium acetate, calcium acetate, ammonium acetate, sodium carbonate, potassium carbonate, Potassium hydrogen carbonate, sodium hydrogen carbonate or ammonium carbonate, Organic lithium compounds such as n-butyllithium and tertiary amines such as Trimethylamine, triethylamine, tributylamine, di-isopropylethylamine, tetra methylguanidine, N, N-dimethylaniline, pyridine, piperidine, N-methylpiperidine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclonones (DBN) or diazabicycloundecene (DBU).  

In cases where A in formula (III) represents an alcohol, alkanoyloxy or Alkoxy group, organic or arrive as reaction aids organic acids, such as sulfuric acid, hydrochloric acid, p-toluene sulfonic acid, perfluorobutanesulfonic acid or strongly acidic ion exchanger in question.

The method according to the invention can optionally also be carried out in a two phase system, such as water / toluene or water / dichloromethane, given if carried out in the presence of a suitable phase transfer catalyst will. Examples of such catalysts are: Tetra butylammonium iodide, tetrabutylammonium bromide, tetrabutylammonium chloride, Tributyl-methylphosphonium bromide, trimethyl-C₁₃ / C₁₅-alkylammonium chloride, Trimethyl-C₁₃ / C₁₅-alkylammonium bromide, dibenzyl-dimethyl-ammoniummethyl sulfate, dimethyl-C₁₂ / C₁₄-alkylbenzylammonium chloride, dimethyl-C₁₂ / C₁₄-alkyl benzylammonium bromide, tetrabutylammonium hydroxide, triethylbenzylammo nium chloride, methyltrioctylammonium chloride, trimethylbenzylammonium chloride, 15-crown-5, 18-crown-6 or tris [2- (2-methoxyethoxy) ethyl] amine.

The reaction temperatures can be carried out when carrying out the process according to the invention Process can be varied over a wide range. Generally works one at temperatures between -70 ° C and + 200 ° C, preferably at Temperatures between 0 ° C and 130 ° C.

The process according to the invention is usually carried out under normal pressure leads. However, it is also possible to increase or decrease the pressure work.

To carry out the process according to the invention, one uses per mole 1H-Imidazole of formula (II) generally 1.0 to 5.0 mol, preferably 1.0 to 52.5 mol of compound of the formula (III) and optionally 0.01 to 5.0 mol, preferably 1.0 to 3.0 moles of reaction auxiliaries.

In a special embodiment, it is also possible to use the 1H-imidazoles Formula (II) initially in a preceding reaction step with the help of conventional Silylation processes, for example with hexamethyldisilazane or trimethylsilyl chloride, optionally in the presence of a suitable catalyst, as in  for example sulfuric acid, trifluoroacetic acid, ammonium sulfate, imidazole or To silylate saccharin at temperatures between -20 ° C and + 50 ° C and so available 1-Trimethylsilylimidazole in a subsequent second stage with Alkylating agents of formula (II) according to the inventive method to implement. In this case it is advantageous as a catalyst for alkylation reaction to add tin tetrachloride (see, for example, Chem. Heterocycl. Comp. USSR 24, 514 (1988)).

Carrying out the reaction, working up and isolating the reaction products takes place according to known methods (see also the production examples).

The end products of the formula (I) are purified with the aid of customary ones Processes, for example by column chromatography or by recrystalline lize.

The characterization takes place with the help of the melting point or with non-crystalline lizing compounds, for example, with the help of proton nuclear magnetic resonance spectroscopy (1 H-NMR).

The active substances are suitable for controlling animal pests, preferably arthropods and nematodes, in particular insects and arachnids, which occur in agriculture, in forests, in the protection of stored goods and materials and in the hygiene sector. They are effective against normally sensitive and resistant species as well as against all or individual stages of development. The pests mentioned above include:
From the order of the Isopoda 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 spec.
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. Blatta orientalis, Periplaneta americana,
Leucophaea maderae, Blattella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis, Schistocerca gregaria.
From the order of the Dermaptera z. B. Auricular Forficula.
From the order of the Isoptera z. B. Reticulitermes spp.
From the order of the Anoplura z. B. Phylloxera vastatrix, Pemphigus spp., Pediculus humanus corporis, Haematopinus spp., Linognathus spp.
From the order of the Mallophaga z. B. Trichodectes spp., Damalinea spp.
From the order of the Thysanoptera z. B. Hercinothrips femoralis, Thrips tabaci.
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, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp., Phorodaliphasumum., Phorodaliphasum bilobatus, Nephotettix cincticeps, Lecanium corni, Sais setia 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 maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp. Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Spodoptera exigua, Mamestra brassicae, Panolis flammea, Prodenia litura, Spodoptera spp., Trichoplocapsia n. , Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinea pellionella, Hofmannophila pseudospretella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnidana, Homona magnidanana.
From the order of the Coleoptera z. B. Anobium punctatum, Rhizopertha dominica, Acanthoscelides obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes chrysoceppus, st spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus sppium, sides., Nipt ., Tenebrio molitor, Agriotes spp., Cono derus spp., Melolontha melolontha, Amphimallon solsti tialis, 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., Stomox ., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa.
From the order of the Siphonaptera z. B. Xenopsylla cheopis, Ceratophyllus spp.
From the order of the Arachnida z. B. Scorpio maurus, Latrodectus mactans.
From the order of Acarina z. B. Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Choroptes spp.,. Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp.

The active compounds according to the invention are notable for high insecticidal and acaricidal effectiveness.

They can be used to control plants with particularly good success harmful insects, such as against the larvae of horseradish Leaf beetle (Phaedon cochleariae) or against the larvae of the green leafhopper (Nephotettix cincticeps) against the caterpillars of the cockroach (Plutella maculipennis).  

The active compounds according to the invention also have a fungicidal activity, for example against Pyricularia oryzae and against powdery mildew.

The active compounds according to the invention can also be used as defoliants, desiccants, Herbicides and especially used as weed killers will. Weeds in the broadest sense are understood to mean all plants that are on Growing up in places where they are undesirable. Whether the substances according to the invention as total or selective herbicides act depends essentially on the averted crowd.

The active compounds according to the invention can, for. B. ver in the following plants be applied:

Dicot weeds of the genera:
Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippia, Rotor Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum.

Dicotyledon cultures of the genera:
Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, 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, Cypems, Sorghum, Agropyron, Cycnodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Sphenylumum, Ihenoceaum Agrostis, Alo pecurus, Apera.

Monocot cultures of the genera:
Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghum, Panicum, Sachharum, Pineapple, Asparagus, Allium.

However, the use of the active compounds according to the invention is by no means limited to limited to these genera, but also extends in the same way other plants.

The compounds are suitable depending on the concentration Total weed control e.g. B. on industrial and track systems and on paths and Places with and without tree cover. Likewise, the connections to Weed control in permanent crops, e.g. B. forest, ornamental trees, fruit, wine, Citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and Hop plants, on ornamental and sports turf and pastures and for selective Weed control can be used in annual crops.

The active compounds according to the invention are very suitable for selective Control of monocotyledon weeds in dicotyledon crops before and after method. You can, for example, in cotton or beet with very good success can be used to control harmful grass.

The active ingredients can be converted into the usual formulations, such as Solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient impregnated natural and synthetic materials as well as very fine encapsulation in polymeric fabrics.

These formulations are prepared in a known manner, e.g. B. by Mixing the active ingredients with extenders, i.e. liquid solvents and / or solid carriers, optionally using surfaces active agents, ie emulsifiers and / or dispersants and / or foam generating 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 Alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons substances such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic Koh hydrogen, 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 cyclo hexanone, 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, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders, such as highly disperse silica, aluminum oxide and silicates, are suitable as solid carriers for granules: 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 tobacco stems; as emulsifying and / or foam-generating agents come into question: z. B. nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. B. alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; as dispersing agents come into question: z. B. lignin sulfite and methyl cellulose.

In the formulations, adhesives such as carboxymethyl cellulose, ver natural and synthetic polymers in powder, granular or latex form be used, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and na natural phospholipids such as cephalins and lecithins and synthetic phos pholipid. Other additives can be mineral and vegetable oils.

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

The formulations generally contain between 0.1 and 95% by weight Active ingredient, preferably between 0.5 and 90%.

The active substance according to the invention can be present in its commercially available formulations and in the use forms prepared from these formulations in a mixture with other active substances, such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth-regulating substances or herbicides. Insecticides include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, chlorinated hydrocarbons, phenylureas, substances produced by microorganisms and others
Particularly cheap mixing partners are e.g. B. the following:

Fungicides:
2-aminobutane; 2-anilino-4-methyl-6-cyclopropyl-pyrimidine; 2 ′, 6′-dibromo-2-methyl-4′-trifluoromethoxy-4′-trifluoromethyl-1,3-thiazole-5-carboxanide; 2,6-di chloro-N- (4-trifluoromethylbenzyl) benzamide; (E) -2-methoxyimino-N-methyl-2- (2-phenoxyphenyl) acetamide; 8-hydroxyquinoline sulfate; Methyl- (E) -2 - {- 2- [6- (2-cyano phenoxy) pyrimidin-4-yloxy] phenyl} -3-methoxyacrylate; Methyl (E) methoximino [alpha- (o-tolyloxy) -o-tolyl] acetate; 2-phenylphenol (OPP), aldimorph, ampropylfos, anilazine, azaconazole,
Benalaxyl, Benodanil, benomyl, Binapaciyl, biphenyl, bitertanol, blasticidin-S, bromuconazole, Bupirimate, Buthiobate, calcium polysulfide, captafol, captan, carbendazim, carboxin, chinomethionat (Quinomethionat), chloroneb, chloropicrin, chlorothalonil, chlozolinate, Cufraneb, cymoxanil, cyproconazole Cyprofuram
Dichlorophene, diclobutrazole, diclofluanid, diclomezin, dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole, dinocap, diphenylamine, dipyrithione, ditalimfos, dithianon, dodine, drazoxolone,
Edifenphos, epoxyconazole, ethirimol, etridiazole,
Fenarimol, Fenbuconazole, Fenfuram, Fenitropan, Fenpiclonil, Fenpropidin, Fenpropimorph, Fentinacetat, Fentinhydroxyd, Ferbam, Ferimzone, Fluazinam, Fludioxonil, Fluoromide, Fluquinconazole, Flusilazole, Flusulfamide, Flutolanyl, Fuberilafil, Fuberri Furmecyclox,
Guazatine,
Hexachlorobenzene, hexaconazole, hymexazole,
Imazalil, Imibenconazol, Iminoctadin, Iprobefos (IBP), Iprodione, Isoprothiolan,
Kasugamycin, copper preparations, such as: copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, oxine copper and Bordeaux mixture,
Mancopper, Mancozeb, Maneb, Mepanipyrim, Mepronil, Metalaxyl, Metconazol, Methasulfocarb, Methfuroxam, Metiram, Metsulfovax, Myclobutanil,
Nickel dimethyldithiocarbamate, nitrothal isopropyl, Nuarimol,
Ofurace, oxadixyl, oxamocarb, oxycarboxin,
Pefurazoate, penconazole, pencycuron, phosdiphen, phthalide, pimaricin, piperalin, polycarbamate, polyoxin, probenazole, prochloraz, procymidon, propamocarb, propiconazole, propineb, pyrazophos, pyrifenox, pyrimethanil, pyrozeno, Quintzenil, Quintzenil, PCint
Sulfur and sulfur preparations,
Tebuconazole, tecloftalam, tecnazene, tetraconazole, thiabendazole, Thicyofen, thiophanate-methyl, thiram, Tolclophos-methyl, tolylfluanid, triadimefon, triadimenol, triazoxide, Trichlamid, tricyclazole, tridemorph, triflumizole, triforine, triticonazole,
Validamycin A, vinclozolin,
Zineb, ziram
Bactericides:
Bronopol, dichlorophene, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone, furan carboxylic acid, oxytetracycline, probenazole, streptomycin, tecloftalam, copper sulfate and other copper preparations.
Insecticides / acaricides / nematicides:
Abamectin, Abamectin, AC 303 630, Acephat, Acrinathrin, Alanycarb, Aldicarb, Alphamethrin, Amitraz, Avermectin, AZ 60541, Azadirachtin, Azinphos A, Azinphos M, Azocyclotin,
Bacillus thuringiensis, Bendiocarb, Benfuracarb, Bensultap, Betacyluthrin, Bifenthrin, BPMC, Brofenprox, Bromophos A, Bufencarb, Buprofezin, Butocarboxin, Butylpyridaben,
Cadusafos, Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, CGA 157 419, CGA 184699, Chloethocarb, Chlorethoxyfos, Chlorfenvinphos, Chlorfluazuron, Chlormephos, Chlorpyrifos, Chlorpyrifos M, Cis-Resmethrin, Clocythrinhrhrhrinhrhrinhrinhrinhrinhrinhrinhrinhrinhrinhrinhrinhrinhrinhrinhrinhrinhrinhrinhrinhrinhrofhrinhrinhrinhrinhrinhrinhrinhrinhrinhrinhrinhrofhrinhrinhrinhrinhrinhrinhrinhrinhrinhrofhrinhrinhrinhrhrinhrhrinhrhrinhrhrinhrinhrofhrinophhrinhrinhrinhrinhrinhrinhrinhrinhrinhrhrinhrhrinhrinhrhrinhrhrinhrhrinhrhrinhrofhrine Cyhexatin, cypermethrin, cyromazine,
Deltamethrin, Demeton M, Demeton S, Demeton-S-methyl, Diafenthiuron, Diazinon, Dichlofenthion, Dichlorvos, Dicliphos, Dicrotophos, Diethion, Diflubenzuron, Dimethoat, Dimethylvinphos, Dioxathion, Disulfoton,
Edifenphos, Emamectin, Esfenvalerat, Ethiofencarb, Ethion, Ethofenprox, Ethoprophos, Etrimphos,
Fenamiphos, Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate, Fipronil, Fluazinam, Flucycloxuron, Flucythrinat, Flufenoxuron, Flufenothxinfox, Fufionophon, Fufionophon, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufon
HCH, heptenophos, hexaflumuron, hexythiazox,
Imidacloprid, Iprobefos, Isazophos, Isofenphos, Isoprocarb, Isoxathion, Ivemectin,
Lamda-cyhalothrin, Lufenuron,
Malathion, Mecarbam, Mervinphos, Mesulfenphos, Metaldehyde, Methacrifos, Methamidophos, Methidathion, Methiocarb, Methomyl, Metolcarb, Milbemectin, Monocrotophos, Moxidectin,
Naled, NC 184, M 25, Nitenpyram,
Omethoate, Oxamyl, Oxydemethon M, Oxydeprofos,
Parathion A, parathion M, permethrin, phenthoate, phorate, phosalone, phosmet, Phosphamdon, phoxim, pirimicarb, pirimiphos M, Primiphos A, profenofos, promecarb, propaphos, propoxur, prothiofos, prothoate, pymetrozine, Pyrachlophos, Pyradaphenthion, Pyresmethrin, pyrethrum, Pyridaben, pyrimidifen, pyriproxifen,
Quinalphos,
RH 5992,
Salithion, Sebufos, Silafluofen, Sulfotep, Sulprofos,
Tebufenozid, Tebufenpyrad, Tebupirimphos, Teflubenzuron, Tefluthrin, Temephos, Terbam, Terbufos, Tetrachlorvinphos, Thiafenox, Thiodicarb, Thiofanox, Thiomethon, Thionazin, Thuringiensin, Tralomenethriazonium, Triomenethriazonium, Tri
Vamidothione, XMC, xylylcarb, YI 5301/5302, zetamethrin.

Herbicides:
for example anilides, such as. B. Diflufenican and Propanil; Arylcarboxylic acids, such as. B. dichloropicolinic acid, dicamba and picloram; Aryloxyalkanoic acids, such as. B. 2.4 D, 2.4 DB, 2.4 DP, fluroxypyr, MCPA, MCPP and triclopyr; Aryloxy-phenoxy alkanoic acid esters, such as. B. diclofop-methyl, fenoxaprop-ethyl, fluazifop-butyl, haloxyfop-methyl and quizalofop-ethyl; Azinones, such as B. Chloridazon and Norflurazon; Carbamates, e.g. B. Chlorpropham, Desmedipham, Phenmedipham and Propham; Chloroacetanilides such as e.g. B. alachlor, acetochlor, butachlor, metazachlor, metolachlor, pretilachlor and propachlor; Dinitroanilines such as e.g. B. Oryzalin, Pendimethalin and Trifluralin; Diphenyl ether, such as. B. acifluorfen, bifenox, fluoroglycofen, fomesafen, halosafen, lactofen and oxyfluorfen; Ureas, such as B. chlorotoluron, diuron, fluometuron, isoproturon, linuron and methabenzthiazuron; Hydroxylamines, such as. B. Alloxydim, Clethodim, Cycloxydim, Sethoxydim and Tralkoxydim; Imidazolinones, e.g. B. Imazethapyr, Imazamethabenz, Imazapyr and Imazaquin; Nitriles such as B. bromoxynil, dichlobenil and ioxynil; Oxyacetamides such as e.g. B. Mefenacet; Sulfonylureas, such as. B. amidosulfuron, bensulfuron-methyl, chlorimuron-ethyl, chlorosulfuron, cinosulfuron, metsulfuron-methyl, nicosulfuron, primisulfuron, pyrazosulfuron-ethyl, thifensulfuron-methyl, triasulfuron and tribenuron-methyl; Thiol carbamates such as e.g. B. butylates, cycloates, dialallates, EPTC, esprocarb, molinates, prosulfocarb, thiobencarb and triallates; Triazines, e.g. B. Atrazin, Cyanazin, Simazin, Simetryne, Terbutryne and Terbutylazin; Triazinones such as e.g. B. hexazinone, metamitron and metribuzin; Others, such as B. aminotriazole, benfuresate, bentazone, cinmethylin, clomazone, clopyralid, difenzoquat, dithiopyr, ethofumesate, fluorochloridone, glufosinate, glyphosate, isoxaben, pyridate, quinchlorac, quinmerac, sulphosate and tridiphane.

The active ingredient according to the invention can also be in its commercially available form formulations and in the application forms prepared from these formulations in a mixture with synergists. Synergists are connections through which the effect of the active ingredients is increased without the added synergist must be actively active itself.  

The active ingredient content of the prepared from the commercially available formulations Application forms can vary widely. The drug concentration the use forms can be from 0.000000 to 95% by weight of active compound, preferably 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 stands out Active ingredient through an excellent residual effect on wood and clay as well due to good stability to alkali on limed substrates.

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

Manufacturing examples

example 1

4.1 g (0.02 mol) of 2-trifluoromethyl-4,5-dichlorimidazole and 5.52 g (0.04 mol) Potassium carbonate is placed in 100 ml acetone and mixed with 3.87 g (0.02 mol) N-Chloromethyl-N-iso-butyl-carbamic acid ethyl ester was added. After 16 hours Stirring at 20 ° C is filtered off from the solid, the filtrate is concentrated and the Chromatograph the residue on silica gel with methylene chloride as the eluent. 4.42 g (56% of theory) of the compound of the above formula are obtained as yellowish oil.

1 H-NMR (CDCl₃): δ = 0.84 (m, 6H, CH₃); 1.18 (t, 3H, OEt); 1.86 (m, 1H, CH); 4.10 (g, 2H, OEt); 5.73 (s, 2H, NCH₂N).

Example 2

A solution of 2.97 g (0.0175 mol) of 2-trifluoromethyl-4,5-dichlorimidazole in 10 ml THF becomes a suspension of 0.75 g (0.025 mol) cooled to 0 ° C NaH (as an 80% mineral oil dispersion) dropped in 25 ml THF. After 40 min The imidazole salt solution is stirred at 50 ° C. to a solution of 2.49 g (0.019 mol) of N-acetoxymethylacetamide in 20 ml of THF and added for 5 hours  Reflux heated. The reaction mixture is cooled, carefully to 250 ml Poured ice water and extracted with methylene chloride (4 × 150 ml). The organic phases are dried over MgSO₄, concentrated in vacuo and the residue on silica gel with CH₂Cl₂ / EtOH = 9: 1 as the eluent chromato graphed, whereby 1.6 g (30% of theory) of the above compound as a colorless oil be preserved.

1 H-NMR (CDCl₃): δ = 2.05 (s, 3H, CH₃); 5.57 (s, 2H, CH₂N); 6.48 (s, 1H, NH).

Example 3

3.54 g (0.015 mol) of 2-N- (tert-butyl) aminocarbonyl-4,5-dichloroimidazole and 3.0 g of potassium carbonate are placed in 150 ml of dichloromethane. To this is added 2.84 g (0.019 mol) of N-chloromethyl-N-methyl-carbamic acid ethyl ester and the mixture is heated to reflux for 16 hours. The solid is then filtered off with suction, the filtrate washed three times with water, dried with magnesium sulfate and concentrated after the desiccant has been separated off. The beige-colored crude product is filtered chromatographically on silica gel with dichloromethane as the eluent. 4.73 g (89.9% of theory) of product (colorless solid) of the formula shown above with a melting point of 79 ° C. are obtained.

Examples of use Example A Pre-emergence test

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

To produce a suitable preparation of active compound, mix 1 Part by weight of active ingredient with the specified amount of solvent gives the specified amount of emulsifier and dilute the concentrate with water to the desired concentration.

Seeds of the test plants are sown in normal soil. After 24 hours the soil is poured with the active ingredient preparation. You keep the The amount of water per unit area expediently constant. The effect Concentration of substances in the preparation does not matter, only the decisive factor Application rate of the active ingredient per unit area. 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

Example B Post emergence test

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

To produce a suitable preparation of active compound, mix 1 Part by weight of active ingredient with the specified amount of solvent gives the specified amount of emulsifier and dilute the concentrate with water to the desired concentration.

Test plants with a height of 5 are sprayed with the active ingredient preparation have up to 15 cm so that the desired amounts of active ingredient per Area unit are applied. The concentration of the spray liquor is like this chosen that the desired amounts of active ingredient in 2000 l of water / ha be applied. After three weeks, the degree of damage to the plants rated in% damage compared to the development of the untreated Control. It means:

0% no effect (like untreated control)
100% total annihilation

Example C Phaedon larval test

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

To produce a suitable preparation of active compound, mix 1 Part by weight of active ingredient with the stated amount of solvent and specified amount of emulsifier and dilute the concentrate with water to the desired concentration.

Cabbage leaves (Brassica oleracea) are dipped into the active ingredient preparation the desired concentration and treated with horseradish leaf beetle larvae (Phaedon cochleariae) occupied while the leaves are still moist.

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

In this test, e.g. B. the compounds according to the preparation examples 9, 16, 35, 22 and 36 at an exemplary active ingredient concentration of 0.1% 100% kill after 7 days.  

Example D Plutella test

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

To produce a suitable preparation of active compound, mix 1 Part by weight of active ingredient with the stated amount of solvent and specified amount of emulsifier and dilute the concentrate with water to the desired concentration.

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

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

In this test, e.g. B. the compounds according to the preparation examples 35, 26, 36, 27 and 29 with an exemplary active ingredient concentration of 0.1% 100% kill after 7 days.  

Example E Heliothis virescens test

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

To produce a suitable preparation of active compound, mix 1 Part by weight of active ingredient with the stated amount of solvent and specified amount of emulsifier and dilute the concentrate with water to the desired concentration.

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

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

In this test, e.g. B. the connection according to preparation example 16 an exemplary active ingredient concentration of 0.1% a kill of 100% after 7 days.  

Example F Nephotettix test

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

To produce a suitable preparation of active compound, mix 1 Part by weight of active ingredient with the stated amount of solvent and specified amount of emulsifier and dilute the concentrate with water to the desired concentration.

Rice seedlings (Oryza sativa) are dipped into the active ingredient preparation the desired concentration and treated with the green rice leafhopper (Nephotettix cincticeps) occupied while the seedlings are still moist.

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

In this test, e.g. B. the compound according to preparation example 29 an exemplary active ingredient concentration of 0.1% a kill of 100% after 6 days.  

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

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

To produce a suitable preparation of active compound, mix 1 Part by weight of active ingredient with the stated amount of solvent and specified amount of emulsifier and dilute the concentrate with water to the desired concentrations.

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%. Here means 100% that all spider mites have been killed; 0% means that none Spider mites have been killed.

In this test, e.g. B. the compounds according to the preparation examples 12 and 35 with an exemplary active ingredient concentration of 0.01% At least 80% killed after 7 days.

Claims (10)

1. N-substituted imidazoles of the formula (I) in which
R¹ represents hydrogen or represents optionally substituted alkyl, alkoxy or aryl,
R² stands for cyano or for optionally substituted amino,
Y¹ and Y² are independently halogen,
X¹, X² and X³ are independently halogen or together are nitrogen or
X¹ and X² together represent oxygen and
X³ represents in each case optionally substituted amino, alkyl, alkoxy or alkylthio. 2. N-substituted imidazoles of the formula (I) according to claim 1, in which
R¹ is hydrogen, is in each case optionally substituted by halogen C₁-C₈-alkyl or C₁-C durch-alkoxy or is phenyl which is monosubstituted or polysubstituted by identical or different substituents, the following being suitable as substituents:
Halogen, cyano, nitro, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkyl thio, C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkyl, C₁-C₆-haloalkoxy, C₁ -C₆-haloalkylthio, C₁-C₆-haloalkyl sulfinyl, C₁-C₆-haloalkylsulfonyl each having 1 to 13 identical or different halogen atoms, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-alkoxy-C₁-C₆-alkoxy , C₁-C₆-alkylcarbonyl, C₁-C₆-alkoxy carbonyl, C₁-C₆-alkoximino-C₁-C₆-alkyl, optionally one or more times, identically or differently by halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl with 1 up to 10 identical or different halogen atoms substituted doubly linked C₁-C₅-dioxyalkylene or optionally one or more identical or different identical or different phenyl substituted by halogen, C₁-C₆-alkyl or C₁-C₆-haloalkyl with 1 to 13 identical or different halogen atoms,
R² for cyano or for the rest stands,
wherein
R³ represents hydrogen, C₁-C₈-alkyl, C₂-C₈-alkenyl, C₃-C₈-cycloalkyl or phenyl which is monosubstituted or polysubstituted by identical or different substituents, the phenyl substituents mentioned in R¹ being suitable, and
R⁴ for formyl, CONH (C₁-C₈-alkyl), CON (C₁-C₈-alkyl) ₂, CSNH (C₁-C₈-alkyl), CSN (C₁-C₈-alkyl) ₂, SO₂NH (C₁-C₈-alkyl) , SO₂N (C₁-C₈-alkyl) ₂, C₃-C₈-cycloalkyl, C₃-C₈-cycloalkylcarbonyl, C₃-C₈-cycloalkyloxycarbonyl, C₁-C₈-alkylcarbonyl, C₃-C₈-alkenylcarbonyl, C₁-C₈-alkoxy carbonyl, C₃- C₈-alkenyloxycarbonyl, C₁-C₈-alkylthiocar bonyl, C₁-C₈-alkoxythiocarbonyl, C₁-C₈-alkylthio-thiocar bonyl, C₁-C₈-alkylsulfonyl, each in the phenyl radical mono- or polysubstituted, identically or differently substituted, phenyl-C₁-C₈-alkyl , Phenyl-C₁-C₈-alkylcarbonyl, phenyl-C₁-C₈ alkyloxycarbonyl, phenyl, phenylcarbonyl, phenyloxycarbo nyl or phenylsulfonyl, where the phenyl substituents mentioned in R¹ are also suitable as phenyl substituents, furthermore optionally substituted by halogen-substituted pyridyloxycarbonyl or pyrimidinyloxycarbon Thienyloxycarbonyl or
R³ and R⁴ together represent C _2- C _6- alkanediylcarbonyl or C₂-C₆- alkanediyloxycarbonyl,
Y¹ and Y² are independently fluorine, chlorine, bromine or iodine,
X¹, X² and X³ independently of one another represent fluorine, chlorine, bromine or iodine or together represent nitrogen or
X¹ and X² together represent oxygen and
X³ represents in each case optionally substituted by halogen C₁-C₈-alkyl, C₁-C₈-alkoxy or C₁-C₈-alkylthio or for optionally substituted one or more times identical or differently substituted amino, where the following are suitable as substituents:
C₁-C₈-alkyl, C₁-C₈-alkoxy, C₂-C₈-alkenyl, C₃-C₁₀-cycloalkyl, C₁-C₈-haloalkyl, C₁-C₈-haloalkoxy, C₂-C₈-haloalkenyl, C _3- C₁₀-halocycloalkyl, each optionally one to three times the same or different substituted by the phenyl radicals mentioned in R¹, phenyl, phenyl-C₁-C₆-alkyl, double-linked ring-closed, optionally interrupted by at least one heteroatom from the series nitrogen, oxygen, sulfur C₂-C₉- Alkanediyl. 3. N-substituted imidazoles of the formula (I) according to claim 1, in which
R¹ represents hydrogen, represents in each case optionally substituted by halogen C₁-C₆-alkyl or C₁-C₆-alkoxy or for phenyl which is monosubstituted to trisubstituted by identical or different substituents, where suitable as substituents:
Fluorine, chlorine, bromine, iodine, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylsulfinyl, C₁-C₄-alkylsulfonyl, C₁-C₄- haloalkyl, C₁- C₄-haloalkoxy, C₁-C₄-haloalkylthio, C₁-C₄-haloalkylsulfinyl, C₁-C₄-haloalkylsulfonyl each having 1 to 9 identical or different halogen atoms, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁ -C₄-alkoxy, C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkoximino-C₁-C₄-alkyl, if appropriate up to five times, the same or different by halogen, C₁-C₄-alkyl, C₁-C₄ -Halogenalkyl with 1 to 8 identical or different halogen atoms substituted doubly linked C₁-C₄-dioxyalkylene or optionally monosubstituted to triple identical or different by halogen, C₁-C₄-alkyl or C₁-C₄-halo genalkyl with 1 to 9 identical or different halogen atoms Phenyl, where halogen represents fluorine, chlorine, bromine. R² for cyano or for the rest stands,
wherein
R³ represents hydrogen, C₁-C₄-alkyl, C₂-C₆-alkenyl, C₃-C₇-cycloalkyl or phenyl which may be monosubstituted to trisubstituted by identical or different substituents, the phenyl substituents mentioned in R¹ being suitable and
R⁴ for formyl, CONH (C₁-C₆-alkyl), CON (C₁-C₆-alkyl) ₂, CSNH (C₁-C₆-alkyl), CSN (C₁-C₆-alkyl) ₂, SO₂NH (C₁-C₆-alkyl) , SO₂N (C₁-C₆-alkyl) ₂, C₃-C₇-cycloalkyl, C₃-C₇-cycloalkylcarbonyl, C ₃ -C ₇ -cycloalkyloxycarbonyl, C₁-C₆-alkylcarbonyl, C₃-C₆-alkenylcarbonyl, C₁-C₆-alkoxycarbonyl, C₃-C₆-alkenyloxycarbonyl, C₁-C₆-alkylthiocarbonyl, C₁-C₆-alkoxythiocarbonyl, C₁-C₆-alkylthio-thiocarbonyl, C₁-C₆-alkylsulfonyl, each in the phenyl radical mono- or polysubstituted, identically or differently substituted, phenyl-C₁-C₆-alkyl , Phenyl-C₁-C₆-alkylcarbonyl, phenyl-C₁-C₆-alkyloxycarbonyl, phenyl, phenylcarbonyl, phenyloxycarbonyl or phenylsulfonyl, where phenyl substituents in each case are the phenyl substituents mentioned in R¹, furthermore optionally substituted by halogen-substituted pyridyloxycarbonyl, pyrimidinyloxycarbonyl or thienyloxycarbonyl or
R³ and R⁴ together represent C₂-C₅-alkanediylcarbonyl or C₂-C₅-alkanediyloxycarbonyl,
Y¹ and Y² are independently fluorine, chlorine, bromine or iodine,
X¹, X² and X³ independently of one another represent fluorine, chlorine or bromine or together represent nitrogen or
X¹ and X² together represent oxygen and
X³ represents in each case optionally substituted by halogen C₁-C₇-alkyl, C₁-C₇-alkoxy or C₁-C₇-alkylthio or for optionally substituted one or more times identical or differently substituted amino, where the following are suitable as substituents:
C₁-C₇-alkyl, C₁-C₇-alkoxy, C₂-C₇-alkenyl, C₃-C₈-cycloalkyl, C₁-C₇-haloalkyl, C₁-C₇-haloalkoxy, C₃-C₇-haloalkenyl, C₃-C₁₀-halogenocycloalkyl, each optionally up to three times the same or different phenyl, phenyl-C₁-C₄-alkyl substituted by the phenyl radicals mentioned in R¹, double-linked ring-closed, optionally broken by at least one heteroatom from the series nitrogen, oxygen, sulfur with C₂-C₆- Alkanediyl. 4. N-substituted imidazoles of the formula (I) according to claim 1, in which
R¹ represents hydrogen, represents in each case optionally substituted by halogen C₁-C₄-alkyl or C₁-C₄-alkoxy or for phenyl which is monosubstituted to trisubstituted by identical or different substituents, where suitable as substituents:
Fluorine, chlorine, bromine, iodine, cyano, nitro, C₁-C₃-alkyl, C₁-C₃-alkoxy, C₁-C₃-alkylthio, C₁-C₃-alkylsulfinyl, C₁-C₃-alkylsulfonyl, C₁-C₃- haloalkyl, C₁- C₃-haloalkoxy, C₁-C₃-haloalkylthio, C₁-C₃-haloalkylsulfinyl, C₁-C₃-haloalkylsulfonyl each having 1 to 7 identical or different halogen atoms, C₁-C₃-alkoxy- C₁-C₃-alkyl, C₁-C₃-alkoxy-C₁ -C₃-alkoxy, C₁-C₃-alkylcarbonyl, C₁-C₃-alkoxycarbonyl, C₁-C₃-alkoximino-C₁-C₃-alkyl, optionally one to five times, the same or different by halogen, C₁-C₃-alkyl, C₁-C₃ -Halogenalkyl with 1 to 6 identical or different halogen atoms substituted doubly linked C₁-C₃-dioxyalkylene or optionally single to double identical or different by halogen, C₁-C₃-alkyl or C₁-C₃-halogen alkyl with 1 to 7 identical or different halogen atoms sub substituted phenyl, where halogen represents fluorine, chlorine, bromine,
R² for cyano or for the rest stands,
wherein
R³ represents hydrogen, C₁-C₄-alkyl, C₂-C₄-alkenyl, C₃-C₆-cycloalkyl or phenyl which is monosubstituted or disubstituted by identical or different substituents, the phenyl substituents mentioned in R¹ being suitable and
R⁴ for formyl, CONH (C₁-C₄-alkyl), CON (C₁-C₄-alkyl) ₂, CSNH (C₁-C₄-alkyl), CSN (C₁-C₄-alkyl) ₂, SO₂NH (C₁-C₄-alkyl) , SO₂N (C₁-C₄-alkyl) ₂, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkylcarbonyl, C₃-C₆-cycloalkyloxycarbonyl, C₁-C₄-alkylcarbonyl, C₃-C₄-alkenylcarbonyl, C₁-C₄-alkoxy carbonyl, C₃- C₄-alkenyloxycarbonyl, C₁-C₄-alkylthiocarbo nyl, C₁-C₄-alkoxythiocarbonyl, C₁-C₄-alkylthio-thiocarbo nyl, C₁-C₄-alkylsulfonyl, each in the phenyl radical mono- or disubstituted, identically or differently substituted phenyl-C₁-C₄-alkyl , Phenyl-C₁-C₄-alkylcarbonyl, phenyl-C₁-C₄-alkyloxycarbonyl, phenyl, phenylcarbonyl, phenyloxycarbonyl or phenylsulfonyl, where phenyl substituents in each case are the phenyl substituents mentioned in R¹, furthermore optionally substituted by halogen-substituted pyridyloxycarbonyl, pyrimidinyloxycarbonyl or thienyloxycarbonyl or
R³ and R⁴ together for C₂-C₄-alkanediylcarbonyl or C₂-C₄- alkanediyloxycarbonyl,
Y¹ and Y² are independently fluorine, chlorine, bromine or iodine,
X¹, X² and X³ independently of one another represent fluorine or chlorine or together represent nitrogen or
X¹ and X² together represent oxygen and
X³ represents in each case optionally substituted by halogen C₁-C₆-alkyl, C₁-C₆-alkoxy or C₁-C₆-alkylthio or for optionally substituted one or more times identical or differently substituted amino, where the following are suitable as substituents:
C₁-C₆-alkyl, C₁-C₆-alkoxy, C₂-C₆-alkenyl, C₃-C₇-cycloalkyl, C₁-C₆-haloalkyl, C₁-C₆-haloalkoxy, C₂-C₆-haloalkenyl, C₃-C₆-halocycloalkyl, each optionally one to three times the same or different phenyl radicals substituted by the phenyl radicals mentioned in R¹, phenyl-C₁-C₃-alkyl, double-linked ring-closed, optionally broken by at least one heteroatom from the series nitrogen, oxygen, sulfur with C₂-C₅- Alkanediyl. 5. A process for the preparation of N-substituted imidazoles of the formula (I) according to claim 1, characterized in that 1H-imidazoles of the formula (II) in which
X¹, X², X³, Y¹ and Y² have the meaning given in claim 1,
with compounds of the formula (III) in which
M stands for a suitable leaving group, and
R¹ and R² have the meaning given above
if appropriate in the presence of a diluent and if appropriate in the presence of a reaction auxiliary. 6. pesticides and herbicides, characterized by a Content of at least one N-substituted imidazole of the formula (I) ge according to claim 1. 7. Use of N-substituted imidazoles of the formula (I) according to An saying 1 to combat pests and unwanted plants overgrown. 8. A method for controlling pests, characterized in that N-substituted imidazoles of the formula (I) according to Claim 1 Pests, unwanted vegetation and / or their habitat can act. 9. Process for the preparation of pesticides and herbi ziden, characterized in that N-substituted imidazoles of Formula (I) according to claim 1 with extenders and / or surfaces active funds mixed.