DE19548914A1 - New 4,5-di:cyano-imidazole cpds. - Google Patents

Abstract

4,5-Dicyano-imidazole derivs. of formula (I), and their addn. cpds., are new: R1 = 1-6C haloalkyl, 1-6C hydroxyalkyl, dihydroxy(1-6C)alkyl, or a gp. -(1-6C alkylene)-A; A = 1-6C haloalkoxy, 1-6C haloalkylthio, 1-6C haloalkylsulphinyl, 1-6C hydroxyalkyl, T'CO, phenyl or benzodioxolyl; phenyl or naphthyl (both opt. substd. by 1-3 Q), a 5-membered, opt. aromatic, mono- or bi-cyclic heterocyclic gp. (which contains 1-3 N, O and/or S atoms), opt. substd. by 1-3 halo or R; a 6-membered, non-aromatic, mono- or bi-cyclic heterocycle (contg. 1-3 N, O and/or S atoms), opt. substd. by 1-3 Q' or by one gp. Ar); or an aromatic, mono- or bicyclic 6-membered ring (contg. 1-3 N atoms), opt. substd. by 1-3 gps. selected from halo, NO2, CN, R, 3-7C cycloalkyl, RO, 1-4C hydroxyalkyl, R'CO, R'OCO, OH, CHO, phenyl (opt. substd. by 1-3 halo, NO2, 1-3C (halo)alkyl, 1-3C alkoxy or R'CO), pyridyl, pyrimidinyl or R' (substd. by 1-3 R'O); Q = halo, NO2, CN, T, 1-6C hydroxyalkyl, 1-6C cyanoalkyl, TO, TS, TSO, T'SO2, (T')2N, T'OCO, T'CO, T'COO or COOH); Q' = 3-7C cycloalkyl or Q; Ar = phenyl, benzyl, benzodioxole- (1-4C)alkylene, pyridinyl, pyrimidinyl or phenyl(1-4C)alkylene (all opt. ring substd. by 1-3 Q (with the exception of 1-6C hydroxyalkyl); R2 = T, TO, 3-7C cycloalkyl, TS, TSO, OH, COOH, halo, NO2, CN, NH2, NHT', N(T')2, T'OCO, T'CO, T'CONH or T'OCONH; T = 1-6C (halo)alkyl; T' = 1-6C alkyl; R = 1-4C (halo)alkyl; R' = 1-4C alkyl; R3, R4 = H or a gp. as R2.

Description

The present invention relates to novel 2-phenyl-4,5-dicyanoimidazolyl derivatives of following formula I, in addition to anthelmintic, acaricidal, especially insecticidal Activity and, therefore, against different, important in the agricultural area Have pests inserted. To emphasize their activity against flies and Scrape. The invention further relates to pharmaceutical agents and Schädlingsbe It is also based on the compounds of the formula I. It also relates to the Production of active substances and agents and their use for controlling Helminths, in particular cestodes and trematodes in warm-blooded animals, in particular at Domestic and farm animals, and especially their use for controlling pest from the order of the arthropods, preferably the control of insects.

The new 2-phenyl-4,5-dicyanoimidazolyl derivatives have the following formula I.

wherein
R₁ is C₁-C₆ haloalkyl, C₁-C₆ hydroxyalkyl, C₁-C₆ dihydroxyalkyl or one of the groups
- [C₁-C₆-alkylenyl] -A₁,
- [C₁-C₆-alkylenyl] -A₂,
- [C₁-C₆-alkylenyl] -A₃,
- [C₁-C₆-alkylenyl] -A₄,
- [C₁-C₆-alkylenyl] -A₅ or
- [C₁-C₆-alkylenyl] -A₆ represents, wherein
A₁ is C₁-C₆ haloalkoxy, C₁-C₆ haloalkylthio, C₁-C₆ haloalkylsulfinyl, C₁-C₆ hydroxyalkyl, C₁-C₆ alkylcarbonyloxy, phenyl or benzdioxolyl;
A₂ is phenyl or naphthyl, each selected from one to three substituents selected from the group consisting of halogen, nitro, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-hydroxy alkyl, C₁-C₆-cyanoalkyl, C₁ -C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl di (C₁-C₆-alkyl) amino, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbonyl, C₁-C₆ alkyl carbonyloxy and COOH are substituted;
A₃ is a five-membered aromatic, mono- or annelated bicyclic heterocycle represented by one to three heteroatoms selected from the series consisting of nitrogen, oxygen and sulfur, which is unsubstituted or mono- to disubstituted by halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl is;
A₄ represents a five-membered non-aromatic, mono- or fused bicyclic heterocycle having one to three heteroatoms selected from the series consisting of nitrogen, oxygen and sulfur, which is unsubstituted or mono- to trisubstituted by halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl ;
A₅ represents a six-membered non-aromatic, mono- or annelated bicyclic heterocycle having one to three heteroatoms from the group consisting of nitrogen, oxygen and sulfur; which is unsubstituted or substituted by one to three substituents selected from halogen, nitro, cyano, C₁-C₆-alkyl, C₃-C₇-cycloalkyl, C₁-C₆-haloalkyl, C₁-C₆-hydroxyalkyl, C₁-C₆-cyanoalkyl, C₁- C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkyl sulfonyl, di (C₁-C₆-alkyl) amino, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylcarbonyl, C₁-C₆-alkylcarbonyloxy and COOH is substituted or monosubstituted by a substituent selected from phenyl, benzyl, benzodioxole-C₁-C₄-alkylenyl, pyridinyl, pyrimidyl or phenyl C₁-C₄-alkylenyl, wherein each of these latter substituents in the ring member in turn unsubstituted or mono- to trisubstituted by halogen, nitro, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-cyanoalkyl, C₁-C₆- Alkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-Haloalkylsulfinyl, C₁-C Alkylsulfonyl, C₁-C₆-dialkylamino, C₁-C₆-haloalkoxy, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylcarbonyl, C₁-C₆-alkylcarbonyloxy or COOH groups;
A₆ is an unsubstituted or mono- to trisubstituted aromatic, mono- or fused bicyclic, six-membered heterocycle having one to three nitrogen atoms, wherein the substituents are independently selected from the group halogen, nitro, cyano, C₁-C₄-alkyl, C₃ -C₇-cycloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy, C₁-C₄-hydroxyalkyl, C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl, hydroxy, formyl, phenyl, pyridyl, pyrimidinyl , one to three times by halogen, nitro, C₁-C₃-alkyl, C₁-C₃-alkoxy, C₁-C₄-alkylcarbonyl or C₁-C₃-haloalkyl-substituted phenyl and one to three times by C₁-C₄-alkoxy-substituted C₁-C₄- alkyl;
R₂ is C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₃-C₇-cycloalkyl, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-haloalkylsulfinyl, hydroxy, carboxyl, halogen, nitro, cyano, amino, C₁-C₆-alkylamino, di (C₁-C₆-alkyl) amino, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylcarbonyl, C₁-C₆- Alkylcarbonylamino or C₁-C₆alkoxycarbonylamino; and R₃ and R₄ independently have the meaning of R₂ or hydrogen;
including the physiologically acceptable addition compounds.

Typical but not limiting representatives of compounds of formula I are those in which
R₁ is 3,3,3-trifluoropropyl, 2-hydroxyethyl, 2,2,2-trifluoroethoxymethyl, 2- (3,3,3-trifluoropropylthio) ethyl, 2- (trifluoromethylsulfinyl) ethyl, 3-hydroxymethylhexyl, unsubstituted benzyl, im Phenyl moiety one to three times by fluorine, chlorine, bromine iodine, nitro, cyano, methyl, isopropyl, trifluoromethyl, methoxy, trifluoromethoxy, methylthio, 3,3,3-trifluoropropylthio, methylsulfinyl, methylsulfonyl, trifluoromethylsulfinyl, trifluoromethylsulfonyl, hydroxymethyl, methylcarbonyloxy, Methylcarbonyl, ethoxycarbonyl,
-COOH or dimethylamino-substituted benzyl,

stands;
R₂ is fluoro, chloro, bromo, iodo, trifluoromethyl, methoxy or trifluoromethoxy;
R₃ and R₄ independently have the meaning of R₂ or are hydrogen; this list is only to be understood as an example.

EP-0'283'173 describes 2-phenyl-4,5-dicyanoimidazolyl derivatives with pesticides Properties. Surprisingly, the inventive 2-phenyl-4,5-di cyanoimidazolyl derivatives of the formula I by their specific substitution pattern other spectrum of activity that they use for practical use, especially against insects, like house flies and cockroaches, as well as against animal parasitic helminths in warm-blooded animals makes it suitable.

Surprisingly, the compounds of the formula I according to the invention Because of their specific substitution pattern, a significantly altered biological  Behavior. Compared to the substances from EP-0'283'173 is characterized by the novel Substi tution the spectrum of activity narrower and clear in favor of an anti-fly and above all Anti-cockroach effect has been suspended. This apparent disadvantage will be more than made up, in that the substances according to the invention in contrast to the Substances from EP-0'283'173 also actively combat insects and cockroaches, against Pesticides have become resistant to organophosphorus. This is so important fuller than today still large amounts of organophosphorus compounds against insect pests, however, are used with ever lower efficiency and Resistance problems are almost ubiquitous. The reason for these resistenzbrechenden Properties is not yet clarified, but is undoubtedly ultimately based on the structural difference. On the other hand show the compounds of the invention another advantage that is completely on the side of cockroach control. Cockroaches are extremely mobile insects that spread rapidly and are found everywhere they are offered sufficient food and hiding places. Since you but z. In Households, hospitals, storage warehouses, stables, etc., where they act as disease carriers are extremely undesirable, usually can not combat large-scale with poisons, is they are forced to lure them into traps, where they poisoned poisoned bait Tobe offered. The disadvantage of this is, however, that individuals who only an insufficient Absorb pesticide amount and survive very quickly resistance to the pesticide develop and immediately reduce its impact drastically. It is now with the Substances according to the invention succeeded in getting this problem under control. Combining namely the chemical pesticide of formula I with a biological, Namely with nematodes, which infest and kill cockroaches, it is achieved equal to two extremely beneficial effects. First, the cockroaches are the bait come into contact with nematodes and die even if they only have one insufficient amount of pesticides. Second, the danger of Resis tenzbildung almost completely eliminated and also the cockroach problem through Combination of two completely different principles of action solved much faster than by in each case only one of the principles of action. The user represents a rapid decrease in the Cockroach population. However, this is only possible because the invention Substances show a much narrower spectrum of activity than z. B. the substances EP-0'283'173. The latter show namely a pronounced anti-nematode effect and Therefore, they can not be combined with nematodes. An essential aspect of present invention consists of the combination of the substances according to the invention with cockroach-pathogenic nematodes for controlling insects of the order Blatella.  

In a preferred embodiment, the combination according to the invention is a Compound of formula I with insect-pathogenic nematodes used in one case. This is, for example, a closed device with slots the side walls, which allow the cockroaches to enter the trap. In the upper and lower part is always an agar gel as a water reservoir. On the lower agar gel is a paper insert, for example, was treated as follows: A aqueous suspension of a compound of formula I is sprayed onto the insert, so that 5mg to 500mg active ingredient / m 2 deposit, preferably 10mg to 50mg active ingredient / m 2 A Layer is applied. On the dried paper insert then 1 million applied to 2 million living nematodes. If necessary, the trap still contains other facilities, such as a wooden grid, the cockroaches good hiding place offers possibilities.

The present invention thus also relates in particular to cockroach traps having a moist, sheetlike, absorbent substrate on which living nematodes are immobilized, wherein this carrier additionally 5 mg to 500 mg of a compound of formula I per m² contains. Suitable sheet-like, absorbent substrates are made of porous, absorbent Materials. In particular, come from paper and cardboard, for example, from tissue Natural or synthetic fibers, but also thickened or solidified liquids. Very good is blotting paper.

The present invention relates mainly to the control of cockroaches the order Blattodea, as members of the genus Blatella.

In the definition of the formula I according to the invention, the individual generic Terms are understood as follows:

The term alkyl itself or as part of another substituent are in the Frame of the present invention depending on the number of carbon atoms fol ing straight-chain and branched groups to understand, for. B: methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, tert-butyl, isobutyl, etc. Haloalkyl itself or as Component of haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl for a simple to perhalogenated alkyl substituent, such as. B. for CH₂Cl, CHCl₂, CCl₃, CH₂F, CHF₂, CF₃, CH₂Br, CHBr₂, CBr₃, CH₂J, CJ₃, CHClF, CHBrCl, CFBrCl, C₂F₅, CH₂CH₂Cl, CHClCH₃, C₂Cl₅, CHFCHCl₂, etc., but preferably for CF₃. By halogen is here and below fluorine, chlorine, bromine or iodine, preferably  Fluorine, chlorine or bromine, especially chlorine are understood. Alkylthio stands for Alkyl-S-; Alkylsulfinyl for alkyl-S (O) -; Alkylsulfonyl for alkyl-S (O) ₂-; alkylcarbonyl for alkyl-C (O) -; Alkylcarbonyloxy for alkyl-C (O) -O-; Alkoxycarbonyl for Alkyl-O-C (O) -; Alkylene for a saturated aliphatic bridge member, the unbranched or is branched, z. B. for -CH₂-; -CH₂CH₂-; -CH₂CH₂CH₂-; -CH₂CH₂CH₂CH₂-; -CH₂CH₂CH₂CH₂CH₂-; -CH₂CH₂CH₂CH₂CH₂CH₂-; -CH₂CH (CH₃) -; -CH₂CH (CH₃) CH₂-; -CH₂C (CH₃) ₂-; -CH₂CH (C₂H₅) CH₂-; Etc.

Cycloalkyl itself or as part of a substituent is depending on the number of carbon atoms for cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclo heptyl, etc. Cyanoalkyl represents an alkyl group wherein one to three hydrogen atoms are substituted by CN, preferably an alkyl group in which is a CN group is located at the terminal carbon atom. Accordingly, hydroxyalkyl for an alkyl group in which one to three hydrogen atoms are substituted by OH, preferably an alkyl group in which an OH group on the terminal carbon substance atom is located.

Phenyl-C₁-C₄-alkylene is an unbranched or branched, one to four carbons nitrogen atoms comprehensive alkylene, which is substituted by phenyl, preferably for

Benzdioxol-C₁-C₄-alkylene is an unbranched or branched, one to four Carbon atoms-containing alkylene bridge substituted by benzdioxole, preferably for

As examples of heterocycles in the definitions of A₃ to A₆ are the following Radicals called: pyrrolidinyl, 2-pyrrolinyl, 3-pyridinyl, 1,2,3,4-tetrahydropyridinyl, Piperidinyl, pyrazolidinyl, 3-pyrazolinyl, imidazolidinyl, hexahydropyrimidinyl, Piperazinyl, isoxazolidinyl, morpholinyl, thiazolinyl, 1,2,3-triazolyl, 1,2,4-triazolyl, Thiomorpholinyi, indolinyl, isoindolinyl, perhydroindolinyl, perhydroisoindolinyl, 1,2,3,4-tetrahydroquinolinyl, 1,2,3,4-tetrahydroisoquinolinyl, perhydroquinolinyl, Perhydroisoquinolinyl, benzoxazolidinyl and benzothiazolidinyl.

The substituted, nitrogen-bonded heterocyclic radicals in the definitions of A₃ to A₆ listed below are understood as examples which do not limit the scope of the invention: piperazinyl, 4-methyl-piperazinyl, 4-ethoxycarbonyl-piperazinyl, 4- Benzylpiperazinyl, 4- (2-hydroxyethyl) piperazinyl, 4- (3-chloropropyl) piperazinyl, 4- [2- (2-trifluoromethylphenyl) ethyl] piperazinyl, 4- (5-benzodioxolylmethyl) -piperazinyl, 4-tert-butoxy-carbonyl-piperazinyl, 3,6-dimethyl-piperazinyl, 4-phenyl-piperazinyl, 4- (4-methylphenyl) -piperazinyl, 4- (4-tert-butyl-phenyl) -piperazinyl, 4- (4-fluorophenyl) piperazinyl, 4- (4-acetylphenyl) -piperazinyl, 4- (4-methoxyphenyl) -piperazinyl, 4- (4-chlorophenyl) -piperazinyl, 4- (3-methylphenyl) -piperazinyl, 4- (2,4-dichlorophenyl) piperazinyl, 4- (4-nitrophenyl) piperazinyl, 4- (3-trifluoromethylphenyl) piperazinyl, 4- (2-trifluoromethylphenyl) piperazinyl, 4- (2-methoxyphenyl) piperazinyl, 4- (2-ethoxy-phenyl) -piperazinyl, 4- (2-Huorophenyl) -piperazinyl, 4- (2-chlorophenyl) -piperazinyl, 4- (4-bromophenyl) -piperazinyl, 4- (4-trifluoromethylphenyl) -piperazinyl, 4- (2-pyridyl) - piperazinyl, 4- (2-pyrimidinyl) -piperazinyl,
Piperidinyl, 3-methylpiperidinyl, 4- (4-methoxyphenyl) piperidinyl, 4- (4-chlorophenyl) piperidinyl, 4- (3-methylphenyl) piperidinyl, 4- (2,4-dichlorophenyl) piperidinyl, 4- (4-Nitrophenyl) piperidinyl, 4- (3-trifluoromethylphenyl) piperidinyl, 4- (2-trifluoromethylphenyl) piperidinyl, 4- (2-methoxyphenyl) piperidinyl, 4- (2-ethoxyphenyl) piperidinyl , 4- (2-Fluorophenyl) piperidinyl, 4- (2-chlorophenyl) piperidinyl, 4- (4-bromophenyl) piperidinyl, 4- (4-trifluoromethylphenyl) piperidinyl, 4- (3,5-difluorophenyl) - piperidinyl, 4- (2-pyridyl) piperidinyl, 4- (2-pyrimidinyl) piperidinyl, 3-ethoxycarbonyl-piperidinyl, 3-hydroxymethyl-piperidinyl, 4-hydroxypiperidinyl, 4-methyl-piperidinyl, 4-isopropyl-piperidinyl, 4-tert-butyl-piperidinyl, 4-ethoxycarbonyl-piperidinyl, 4-phenyl-piperidinyl, 3,3-dimethyl-piperidinyl, 4-benzyl-piperidinyl, 4- (2-hydroxyethyl) -piperidinyl,
Morpholinyl, 3,5-dimethylmorpholinyl, 3,5-diisopropylmorpholinyl, thiomorpholinyl, 3,5-dimethylthiomorpholinyl,
Pyrrolidinyl, 2,5-dimethylpyrrolidinyl,
thiazolinyl,
1,2,3,4-tetrahydroisoquinolinyl, 1,2,3,4-tetrahydro-6,7-dimethoxyisoquinolinyl,
Perhydroisoquinolinyl and perhydroisoindolinyl.

The term physiologically contractual addition compounds are complexes or Salts of a compound of formula I with an inorganic or organic acid or base, which by addition of an equivalent amount of a salzbil base with the base molecule of the formula I or with solvents such as  Dimethylformamide (DMF) or dimethylacetamide (DMA). Suitable inorganic Bases are z. As oxides, hydroxides, carbonates and bicarbonates of alkali and Alkaline earth metals (eg CaO, BaO, NaOH, KOH, Ca (OH) ₂, KHCO₃, NaHCO₃, K₂CO₃ or Na₂CO₃). Typical representatives of suitable organic bases are tetrabutyl ammonium hydroxide, trialkylamines such as triethylamine or dialkylamines such as diethyl or Dipropylamine.

Six highlighted subgroups of compounds of formula I form those each characterized by the substituent A₁, A₂, A₃, A₄, A₅ or A₆, wherein A _1- ₆ have the meanings given under formula I; including the Physio logically acceptable addition compounds and among these are particularly preferred those which are substituted in the ring portion of A _1-6 by fluorine, chlorine, bromine, methoxy, ethoxy, trifluoromethyl or trifluoromethoxy.

Within the compounds of the formula I, for example, the following subgroups prefers:

Group A: compounds of the formula I in which
R₁ is [C₁-C₆-alkylenyl] -A₃, wherein A₃ represents a five-membered aromatic, mono- or fused bicyclic heterocycle having one to three hetero atoms selected from the series consisting of nitrogen, oxygen and sulfur, which is unsubstituted or mono- to disubstituted by Halo, C₁-C₄-alkyl or C₁-C₄-haloalkyl is substituted; and
R₂, R₃ and R₄ have the meanings given under formula I.

Group B: compounds of the formula I in the scope of group A, wherein
A₃ is thiazole, each of which is unsubstituted or mono- to disubstituted by halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl; and
R₂, R₃ and R₄ have the meanings given under formula I.

Group C: compounds of the formula I in the scope of group A, wherein
A₃ is benzthiazole, each of which is unsubstituted or mono- to disubstituted by halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl; and
R₂, R₃ and R₄ have the meanings given under formula I.

Group D: compounds of the formula I in which
R₁- represents [C₁-C₆-alkylenyl] -A₆, wherein
A₆ represents an unsubstituted or monosubstituted to trisubstituted aromatic, mono- or fused bicyclic, six-membered heterocycle having one to three nitrogen atoms, wherein the substituents are independently selected from the series fluorine, chlorine, bromine, nitro, cyano, C₁-C₃ Alkyl, C₃-C₆ cycloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkyl, C₁-C₃ haloalkoxy, C₁-C₃ hydroxyalkyl, C₁-C₃ alkylcarbonyl, C₁-C₃ alkoxycarbonyl, hydroxy, formyl, phenyl , Pyridyl, pyrimidinyl, mono- to trisubstituted by fluorine, chlorine, bromine, C₁-C₃Alkoxy, C₁-C₃-alkylcarbonyl or C₁-C₃-haloalkyl-substituted phenyl and mono- to trisubstituted by C₁-C₃-alkoxy C₁-C₃-alkyl ;
R₂ is C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₆-haloalkoxy, C₃-C₆cycloalkyl, C₁-C₃alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-haloalkylsulfinyl, hydroxy, carboxyl, halogen, nitro, cyano, amino, C₁-C₃-alkylamino, di (C₁-C₃-alkyl) amino, C₁-C₃-alkoxycarbonyl, C₁-C₃-alkylcarbonyl, C₁-C₃- Alkylcarbonylamino or C₁-C₃alkoxycarbonylamino; and
R₃ and R₄ independently have the meaning of R₂ or hydrogen; including the physiologically acceptable addition compounds.

Within the group D, especially those compounds are preferred in which
A₆ is pyridine which is unsubstituted or mono- to disubstituted by halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl; and
R₂, R₃ and R₄ have the meanings given for group D and, among these, in particular compounds of the formula I in which
R₁- represents [C₁-C₆-alkylenyl] -A₆, wherein
A₆ is pyridine which is unsubstituted or mono- to disubstituted by fluorine chlorine, bromine, C₁-C₄-alkyl or trifluoromethyl substituted; including the physiologically acceptable addition compounds.

Further interesting subgroups of compounds of the formula I are:

Group E: compounds of the formula I in which
R₁- represents [C₁-C₆-alkylenyl] -A₁, wherein
A₁ is C₁-C₃ haloalkoxy, C₁-C₃ haloalkylthio, C₁-C₃ haloalkylsulfinyl, C₁-C₃ hydroxyalkyl, C₁-C₃ alkylcarbonyloxy, phenyl or benzodioxolyl;
R₂ is C₁-C₃ alkyl, C₁-C₃ haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₃-C₆ cycloalkyl, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, C₁-C₃ alkylsulfinyl, C₁-C₃-haloalkylsulfinyl, hydroxy, carboxyl, halogen, nitro, cyano, amino, C₁-C₃-alkylamino, di (C₁-C₃-alkyl) amino, C₁-C₃-alkoxycarbonyl, C₁-C₃-alkylcarbonyl, C₁-C₃- Alkylcarbonylamino or C₁-C₃alkoxycarbonylamino; and
R₃ and R₄ independently have the meaning of R₂ or hydrogen; including the physiologically acceptable addition compounds.

Group F: Compounds of the formula I in which
R₁- represents [C₁-C₆-alkylenyl] -A₄, wherein
A₄ represents a five-membered non-aromatic, mono- or fused bicyclic heterocycle having one to three heteroatoms selected from the series nitrogen, oxygen and sulfur, which is unsubstituted or mono- to trisubstituted by halogen, C₁-C₃-alkyl or C₁-C₃-haloalkyl ;
R₂ is C₁-C₃ alkyl, C₁-C₃ haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₃-C₆ cycloalkyl, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, C₁-C₃ alkylsulfinyl, C₁-C₃-haloalkylsulfinyl, hydroxy, carboxyl, halogen, nitro, cyano, amino, C₁-C₃-alkylamino, di (C₁-C₃-alkyl) amino, C₁-C₃-alkoxycarbonyl, C₁-C₃-alkylcarbonyl, C₁-C₃- Alkylcarbonylamino or C₁-C₃alkoxycarbonylamino; and
R₃ and R₄ independently have the meaning of R₂ or hydrogen; including the physiologically acceptable addition compounds.

Group G: compounds of the formula I in which
R₁- represents [C₁-C₆-alkylenyl] -A₅, wherein
A₅ represents a six-membered non-aromatic, mono- or annelated bicyclic heterocycle having one to three heteroatoms from the group consisting of nitrogen, oxygen and sulfur; which is unsubstituted or substituted by one to three substituents selected from fluorine, chlorine, bromine, nitro, cyano, C₁-C₃-alkyl, C₃-C₆-cycloalkyl, C₁-C₃-haloalkyl, C₁-C₃-hydroxyalkyl, C₁-C₃ cyanoalkyl, C₁ _-36 alkoxy, C₁-C₃-haloalkoxy, C₁-C₃-alkylthio, C₁-C₃ haloalkylthio, C₁ -C₃-alkylsulfinyl, C₁-C₃ haloalkylsulfinyl, C₁-C₃-alkylsulfonyl, di (C₁-C₃ -alkyl) amino, C₁-C₃-alkoxycarbonyl, C₁-C₃-alkyl carbonyl, C₁-C₃-alkylcarbonyloxy and COOH or is monosubstituted by a substituent selected from the group phenyl, benzyl, benzo-C₁-C₃-alkylenyl, pyridinyl , Pyrimidyl or phenyl-C₁-C₃-alkylenyl wherein each of these latter substituents in the ring member in turn unsubstituted or mono- to trisubstituted by halogen, nitro, cyano, C₁-C₃-alkyl, C₁-C₃-haloalkyl, C₁-C₃-cyanoalkyl, C₁ C₃-alkoxy, C₁-C₃-alkylthio, C₁-C₃-haloalkylthio, C₁-C₃-alkylsulfinyl, C₁-C₃-haloalkylsulfinyl, C₁-C₃ alkylsulfonyl, C₁-C₃ dialkylamino, C₁-C₃ haloalkoxy, C₁-C₃ alkoxycarbonyl, C₁-C₃ alkylcarbonyl, C₁-C₃ alkylcarbonyloxy or COOH;
R₂ is C₁-C₃ alkyl, C₁-C₃ haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₃-C₆ cycloalkyl, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, C₁-C₃ alkylsulfinyl, C₁-C₃-haloalkylsulfinyl, hydroxy, carboxyl, halogen, nitro, cyano, amino, C₁-C₃-alkylamino, di (C₁-C₃-alkyl) amino, C₁-C₃-alkoxycarbonyl, C₁-C₃-alkylcarbonyl, C₁-C₃- Alkylcarbonylamino or C₁-C₃alkoxycarbonylamino; and
R₃ and R₄ independently have the meaning of R₂ or hydrogen; including the physiologically acceptable addition compounds.

Particularly preferred single representatives of the compounds of formula I include:

• - 1 - [(2,6-dibromopyridin-5-yl) methyl] -2 - [(2,6-dichloro-4-trifluoromethyl) -phenyl] - 4,5-dicyano-1H-imidazole;
• - 1 - [(2-chlorothiazol-4-yl) methyl] -2 - [(2,6-dichloro-4-trifluoromethyl) phenyl] - 4,5-dicyano-1H-imidazole;
• - 1 - [(2-chloropyridin-5-yl) methyl] -2 - [(2,6-dichloro-4-trifluoromethyl) phen-yl] - 4,5-dicyano-1H-imidazole;
• 1- (3,5-Ditrifluoromethylbenzyl) -2 - [(2,6-dichloro-4-trifluoromethyl) phen-yl] - 4,5-dicyano-1H-imidazole;
• 1- (N-piperidylethylenyl) -2- [(2,6-dichloro-4-trifluoromethyl) phenyl] - 4,5-dicyano-1H-imidazole;
• 1- (N-morpholinylethylenyl) -2 - [(2,6-dichloro-4-trifluoromethyl) phenyl] - 4,5-dicyano-1H-imidazole;
• - 1 - [(2-chlorothiazol-4-yl) methyl] -2- [2,6-dichlorophenyl] -4,5-dicyano-1H-imidazole;
• - 1- [(2-chloropyridin-5-yl) methyl] -2- [2-chlorophenyl] -4,5-dicyano-1 H -imidazole; under Inclusion of physiologically acceptable addition compounds.

The compounds of formula I are prepared by reacting a compound of  Formula II

wherein the substituents R₁, R₂, R₃ and R₄ are the meanings given under formula I. have cyclized with a suitable oxidizing agent, preferably from a compound of formula II, wherein hydrogen is in place of R₁, so that first a compound of formula I is formed, wherein instead of R₁ is hydrogen, and a radical indicated under R₁, subsequently in the sense of an N-alkylation reaction introduces.

The cyclization reaction can be carried out using cyclization agents known per se become. Suitable cyclizing agents are, for example:

Lead tetraacetate in glacial acetic acid or a mixture of glacial acetic acid and an aromatic, reaction-inert hydrocarbon, such as. As benzene, toluene or xylene [cp. F. F. Stephens et al., J. Chem. Soc., 2971 (1949) and 1722 (1950)].

Iodine in a polar organic solvent, such as. For example, N-methyl-2-pyrrolidone Addition of an inorganic base such as sodium acetate and at elevated temperature [see. EP-269'238].

Organic oxidants, such as 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) in a polar, reaction-inert solvent such as acetonitrile and at elevated Temperature [cf. EP-283'173].

Aqueous organic oxidants, such as sodium hypochlorite [cf. Jpn. Kokai TOKKYO KOHO 79, 112, 861] or N-chlorosuccinimide in a polar, organic Solvents such as N, N-dimethylformamide (DMF) with the addition of a soluble, organi base, such as nicotinamide [cf. Synthesis 1058 (1984)].

Particularly advantageous is the use of iodine / N-methylpyrrolidone as Cycli  sierungsmittel.

In the cyclization, the reaction temperatures are usually at + 20 ° to + 100 ° C, preferably at + 40 ° to + 90 ° C.

In the cyclization can indeed use a compound of formula II, wherein R₁ instead of hydrogen, but is preferably from the free amino Compound and performs the non-hydrogen radical R₁ subsequently by means one of the usual methods. This generally leads to better yields, and the reaction can be carried out analogously to known alkylation methods.

Some of the compounds of formula II are novel and, due to their structure, are especially for the preparation of the active end products of formula I or other active substances suitable with this substructure. They are therefore an important part of the present Invention.

The compounds of formula II are prepared by reacting compounds of the formula VII

wherein R₂, R₃ and R₄ have the meanings given under formula I, with a Compound of formula IX

wherein R₁ has the meanings given under formula I, is reacted.

All reactions with a compound of formula IX can analogously to those in the Literature described reactions are carried out, such. B. analogous to  DE-3,726,044 or R.W. Begland et al., J. Org. Chem. 39, 2341 (1974).

In the reactions with a compound of formula IX is preferably from a compound of formula IX, wherein instead of R₁ is initially hydrogen and leads a non-hydrogen radical R₁ subsequently by means of one of the usual Alkylation methods.

Some of the compounds of formula VII are known or may be prepared analogously to be prepared known representatives, for. As described in J. Chem. Eng. Data 28 39 (1983); R.N. Young et al., Tetrahedron Letters 25, 1753 (1984) or L.C. Raiford et al., J. Amer. Chem. Soc. 52, 4576 (1930).

It has now been found that the compounds of the formula I according to the invention in favorable warm-blooded, fish and plant compatibility valuable active ingredients in the Pest control are. The main indications are in the fight against Insects and among these, especially cockroaches. The order cockroaches, Blattodea (Cockroaches, cockroaches) is one of the hemimetabolic insect orders. Belong to her for example, the German cockroach Blatella germanica, the American cockroach Periplaneta americana, the skull cockroach Biaberus craniifer and the Oriental Cockroach Blatta orientalis. Like all insects, cockroaches in their evolution of the Larva (nymph) to an adult animal (imago) having a metamorphosis, in which each Shedding not only an increase in size but also a gradual approach the organization of Imago brings with it. In addition, larva and imago resemble many features. One last moult leads directly to the Imago. In between, no Doll stage turned on. The compounds of the formula I show an excellent Cockroach effect by intervening significantly in their complex life cycle. Some representatives of the substances according to the invention also show a certain anthel Mint activity. The compounds of the invention are all or individual Developmental stages of normally sensitive but also z. B. OP-resistant types of Fly and cockroaches are effective.

A particular feature of the compounds of formula I is their warm-blooded animals surprisingly high tolerability, their OP resistance-breaking property and their To emphasize compatibility for cockroach-pathogenic nematodes.

The main indications are in the control of insects in the hygiene sector,  like cockroaches and flies.

The invention accordingly relates to agents for use in the hygiene sector.

Moreover, the present invention also includes the preparation of these agents, which is characterized by the intimate mixing and / or grinding of the active sub punch with one or more substances or substance groups described herein. The formulation steps can be carried out by kneading, granulating (for granules) and where appropriate, presses (for pellets) are added. Included is also a Prophylactic and / or curative method for controlling plant pests and / or helminths in the mammal, which can be obtained by application of the invention Compounds of the formula I or the agents according to the invention on the habitat of the Pests distinguished.

Active substances of the formula I are usually used in the form of compositions and can be used simultaneously or sequentially with other active ingredients treated area or the parasite. These other active ingredients Both fertilizers, trace element mediators or others can be the plant wax tum affecting preparations. There may also be selective herbicides as well Insecticides, fungicides, bactericides, nematicides, molluscicides or mixtures of several these preparations together with optionally further in the formulation technique Usual carriers, surfactants or other application-promoting additives Verwen find a solution. In particular, living nematodes are also suitable as mixing partners.

The good pesticidal activity of the compounds of the formula I according to the invention corresponds a mortality of at least 50-60% of the mentioned pests.

The effect of the compounds of the invention and the agents containing them against pests can be achieved by adding other insecticides and / or acaricides broaden and adapt to given circumstances. As additions come to Example Representatives of the following classes of active ingredient: Organic phosphorus compounds, nitrophenols and derivatives, formamidines, ureas, carbamates, Pyrethroids, chlorinated hydrocarbons and Bacillus thuringiensis preparations.

The compounds of the formula I are used in unchanged form or preferably used together with the usual in formulation technology tools and  Therefore, for example, emulsifiable concentrates, directly spraying or dilutable solutions, dilute emulsions, wettable powders, soluble powders, Dusts, granules, and encapsulations in polymeric materials in a known manner are processed. The application methods, such as spraying, misting, dusting, Scattering or casting, as well as the means to the desired goals and the given proportions chosen.

A preferred method for applying an active ingredient of the formula I or a made therefrom agent containing at least one of these agents is that Applying to the preferred location of the insect or placing in traps, into which the insect is lured. Application frequency and application rate depend doing so after the infestation pressure of the relevant pathogen. The active substances of the formula I. However, they can also enter the plant via the soil through the root system (systemic effect) by looking at the location of the plant with a liquid zube drenching or introducing the substances in solid form into the soil, eg. B. in the form of Granules (soil application). In water rice crops such granules can the Add flooded rice field. But the compounds of formula I can also on Seeds are applied (coating) by placing the grains either in one liquid preparation of the active ingredient soaks it or with a solid preparation coated.

The formulation, that is, the active ingredient of the formula I, or Kombina tions of these agents with other agrochemical agents, and optionally a solid or liquid additive containing agent, preparations or Compositions are prepared in a known manner, for example by intimate Mixing and / or grinding of the active ingredients with extenders, such as with Solvents, solid carriers, and optionally surface-active Ver compounds (surfactants).

Suitable solvents are: Aromatic hydrocarbons, preferred the fractions C₈ to C₁₂ of alkylbenzenes such as xylene or alkylated Naphthalenes aliphatic or cycloaliphatic hydrocarbons, such as cyclohexane, Paraffins or tetrahydronaphthalene, alcohols such as ethanol, propanol or butanol, and Glycols and their ethers and esters, such as propylene glycol, dipropylene glycol ether, Ethylene glycol, ethylene glycol monomethyl or ethyl ether, ketones such as cyclohexanone, Isophorone or diacetanol alcohol, strong polar solvents such as N-methyl-2-  pyrrolidone, dimethylsulfoxide or dimethylformamide or water, vegetable oils, such as Rapeseed, castor, coconut or soybean oil; optionally also silicone oils.

As solid carriers, for example for dusts and dispersible powders are usually used natural minerals, such as calcite, talc, kaolin, Mont morillonite or attapulgite. To improve the physical properties can also highly dispersed silicas or highly dispersed absorbent polymers added become. As granular, adsorptive granules are porous types, such as pumice, Broken brick, sepiolite or bentonite, as non-sorptive carrier materials calcite or sand in question. In addition, a variety of granular materials inorganic or organic nature, in particular dolomite or crushed plant residues, be used.

As surface-active compounds come, depending on the nature of the active substance to be formulated substance of formula I or combinations of these agents with other insecticides or acaricides nonionic, cationic and / or anionic surfactants with good Emulsifying, dispersing and wetting properties into consideration. Among surfactants are also To understand surfactant mixtures.

Suitable anionic surfactants can be both so-called water-soluble soaps and be water-soluble synthetic surface-active compounds.

As soaps are the alkali, alkaline earth or optionally substituted Ammonium salts of higher fatty acids (C₁₀-C₂₂), such as the sodium or potassium salts of the oil or stearic acid, or of natural fatty acid mixtures, for example can be obtained from coconut or tall oil. Furthermore, as surfactants and the Fatty acid methyl taurine salts.

More often, however, so-called synthetic surfactants are used, especially fat sulfonates, fatty sulfates, sulfonated benzimidazole derivatives or alkylarylsulfonates.

The fatty sulfonates or sulfates are usually as alkali, alkaline earth or gege optionally substituted ammonium salts and generally have an alkyl radical having 8 to 22 carbon atoms, wherein alkyl also includes the alkyl moiety of acyl radicals, for example, the sodium or calcium salt of lignosulfonic acid, dodecyl sulfuric acid ester or a fatty alcohol sulphate prepared from natural fatty acids  mixture used. This subheading also covers the salts of sulfuric acid esters and sulphonic acids of Fatty alcohol ethylene oxide adducts. The sulfonated benzimidazole derivatives contain preferably 2 sulfonic acid groups and one fatty acid residue having about 8-22 C atoms. Alkylarylsulfonates are, for example, the sodium, calcium or triethanolamine salts dodecylbenzenesulfonic acid, dibutylnaphthalenesulfonic acid or a naphthalene sulfonic acid-formaldehyde condensation product. There are also corresponding ones Phosphates, such as salts of the phosphoric ester of a p-nonylphenol (4-14) - Ethylene oxide adduct or phospholipids in question.

Nonionic surfactants are primarily polyglycol ether derivatives of alipha or cycloaliphatic alcohols, saturated or unsaturated fatty acids and Alkylphenols in question, the 3 to 30 glycol ether groups and 8 to 20 carbon atoms in the (aliphatic) hydrocarbon radical and 6 to 18 carbon atoms in the alkyl radical of May contain alkylphenols. Further suitable nonionic surfactants are water-soluble 20 to 250 ethylene glycol ether groups and 10 to 100 propylene glycol Ethylene oxide-containing adducts of polypropyleneglycol, ethylenedi aminopolypropylene glycol and alkylpolypropylene glycol having 1 to 10 carbon atoms in the alkyl chain. The compounds mentioned usually contain per propylene Glycol unit 1 to 5 ethylene glycol units.

Examples of nonionic surfactants are nonylphenolpolyäthoxyäthanole castor oil polyglycol ether, polypropylene-polyethylene oxide adducts, tributylphenoxypolyethoxy ethanol, polyethylene glycol and Oktylphenoxypolyäthoxyäthanol mentioned. Further come also fatty acid esters of polyoxyethylene sorbitan, such as the polyoxyethylene sorbitan trioleate into consideration.

The cationic surfactants are mainly quaternary ammonium salts, which contain as N-substituent at least one alkyl radical having 8 to 22 carbon atoms and as further substituents lower, optionally halogenated alkyl, benzyl or having lower hydroxyalkyl radicals. The salts are preferably in the form of halides, Methyl sulfates or ethyl sulfates, for example, the stearyltrimethylammonium chloride or the benzyl di (2-chloroethyl) ethyl ammonium bromide.

The surfactants commonly used in formulation technology are, for example, in the following Publications described:  

• "McCutcheon's Detergents and Emulsifiers Annual", McPublishing Corp., Glen Rock, NJ, USA, 1988 ",
• H. Stache, "Tensid-Taschenbuch", 2nd ed., C. Hanser Verlag Munich, Vienna 1981.
• M. and J. Ash. "Encyclopedia of Surfactants", Vol. I-III, Chemical Publishing Co., New York, 1980-1981.

The pesticidal preparations for plant protection usually contain 0.1 to 99%, in particular 0.1 to 95% active ingredient of the formula I or combinations of this active ingredient with other insecticides or acaricides, 1 to 99.9% of a solid or liquid additive fabric and 0 to 25%, in particular 0.1 to 25%, of a surfactant. While as Commercial goods tend to be concentrated, the end user uses usually diluted preparations that have significantly lower drug concentrations respectively. Typical application concentrations are between 0.1 and 1000 ppm, preferably between 0.1 and 500 ppm. The application rates per hectare are in the general 1 to 2000 g of active ingredient per hectare, preferably 10 to 1000 g / ha, in particular 20 to 600 g / ha.

Preferred forms of administration for use in warm-blooded animals for control of helminths include solutions, emulsions, suspensions (Drenches), Feed additives, powders, tablets including effervescent tablets, boluses, capsules and Microencapsulations, wherein the physiological compatibility of the Formulation aids is to be respected.

As binders for tablets and boluses come chemically modified, in water or Alcohol-soluble, polymeric natural substances in question, such as starch, cellulose or Protein derivatives (e.g., methylcellulose, carboxymethylcellulose, ethylhydroxyethyl cellulose, proteins such as zein, gelatin and the like) as well as synthetic polymers such as z. Polyvinyl alcohol, polyvinylpyrrolidone, etc. Furthermore, fillers (eg. Starch, microcrystalline cellulose, sugar, lactose, etc.), lubricants and blasts medium included.

Are the anthelmintic agents against animal parasitic helminths in warm-blooded animals in Form of feed concentrates, so serve as carriers z. B. power food, Feed grain or protein concentrates. Such feed concentrates or agents can  besides the active ingredients, additives, vitamins, antibiotics, chemotherapeutics, or other pesticides, notably bacteriostats, fungistats, coccidiostats, or also hormone preparations, substances with anabolic effect or growth-promoting, the quality of meat affecting slaughter animals or otherwise for the Organism containing useful substances. Be the means or the contained therein Active ingredients of the formula I added directly to the feed or cattle drinkers, it contains Ready-to-eat or the finished drinkers, the active ingredients preferably in a concentration of about 0.0005 to 0.02 weight percent (5-200 ppm).

The application of the agents of the invention to the animals to be treated can peroral, parenteral or subcutaneous, the agents being in the form of Solutions, emulsions, suspensions (Drenchs), powders, tablets, boluses and capsules available.

The compositions of the invention generally contain from 0.1 to 99 wt .-%, in particular 0.1 to 95% by weight of active compound of the formula I, Ia or mixtures thereof, 99.9 to 1% by weight, in particular from 99.8 to 5% by weight of a solid or liquid additive, including 0 to 25 wt .-%, in particular 0.1 to 25 wt .-%, of a surfactant.

While as a commodity rather concentrated funds are preferred, uses the Consumers usually diluted funds.

Such agents may contain other additives such as stabilizers, defoamers, viscosity Regulators, binders, adhesives and other agents to achieve special Contain effects.

Such anthelmintic agents used by the end user are also one Component of the present invention.

In each of the inventive method for pest control or the inventive Pesticides can be the active ingredients of the formula I in all their spatial configurations, their mixtures or used in the form of their salts become.

The invention also includes a method for the prophylactic protection of Warm-blooded animals, in particular of domestic, pet and pet animals against parasitic  Helminths, which is characterized in that the active substances of the formula or the drug formulations prepared therefrom as an additive to the food or to the drinkers or also in solid or liquid form orally, by injection or parenterally to the animals applied. The invention also includes the compounds of the formula of the invention I for use in any of said methods.

The following examples serve merely to illustrate the invention without it limit.

In particular, preferred formulations are composed as follows (% = Weight percent):

Emulsifiable concentrates: Active ingredient: 1 to 90%, preferably 5 to 20% Surfactant: 1 to 30%, preferably 10 to 20% liquid vehicle: 5 to 94%, preferably 70 to 85% dusts: @ Active ingredient: 0.1 to 10%, preferably 0.1 to 1% solid carrier: 99.9 to 90%, preferably 99.9 to 99% Suspension concentrates: @ Active ingredient: 5 to 75%, preferably 10 to 50% Water: 94 to 24%, preferably 88 to 30% Surfactant: 1 to 40%, preferably 2 to 30% Wettable powders: @ Active ingredient: 0.5 to 90%, preferably 1 to 80% Surfactant: 0.5 to 20%, preferably 1 to 15% solid carrier material: 5 to 95%, preferably 15 to 90% granules: @ Active ingredient: 0.5 to 30%, preferably 3 to 15% solid carrier: 99.5 to 70%, preferably 97 to 85%

The agents may also contain other additives such as stabilizers, e.g. B. optionally epoxidized vegetable oils (epoxidized coconut oil, rapeseed oil or soybean oil), defoamers, z. Silicone oil, preservatives, viscosity regulators, binders, adhesives as well as fertilizers or other active ingredients for achieving special effects.

The following examples serve to illustrate the invention. They limit the heroin not enter.

The symbol "h" stands for hour, "min" for minute, "N" means normality.

1. Production Example Preparation of 1- [2- (2-chloropyridin-5-yl) methyl] -2 - [(2,6-dichloro-4-trifluoromethyl) phenyl] -4,5-dicyano-1H-imidazole

A mixture of 5.0 g of 2- (2,6-dichloro-4-trifluoromethylphenyl) -4,5-dicyano-1H-imidazole and 2.5 g Anhydrous K₂CO₃ in 300 ml of 2-butanone under nitrogen atmosphere for 2 h under Reflux heated. The heterogeneous solution is then cooled to 25 ° C and gives 2.9 g 2-chloro-5- (chloromethyl) pyridine and 9.0 g NaI. This reaction mixture is allowed to dry for a further 20 h heated to reflux, then cooled and finally filtered. The clear filtrate will completely concentrated. The residue is taken up in 50 ml of ethyl acetate. After that, the Solution again filtered and concentrated. The oily residue is chromatographed on silica gel with ethyl acetate purified by chromatography. The product obtained after concentration is dissolved in 30 ml of ether and precipitated with 25 ml of n-hexane. The crystalline precipitate is filtered off and left to stand for 15 h Temperature dried in a high vacuum. This gives 6.1 g of 1 - [(2-chloropyridin-5-yl) methyl] -2 - [(2,6-dichloro-4-trifluoromethyl) phenyl] -4,5-dicyano-1H-imide-azole having a  Melting point of 160-162 ° C.  

Table 1

2,4-Disubstituted compounds of the formula

Table 2

2,3-Disubstituted compounds of the formula

Table 3

3,4-Disubstituted compounds of the formula

Table 4

2,5-Disubstituted compounds of the formula

Table 5

3,5-Disubstituted compounds of the formula

Table 6

2,6-Disubstituted compounds of the formula

Table 7

Monosubstituted compounds of the formula

2. Formulation examples 2.1. Emulsion concentrates

From these concentrates, by diluting with water emulsions of any desired Concentration are produced.

2.2. Emulsion concentrates

From these concentrates, by diluting with water emulsions of any desired Concentration are produced.

2.3. Suspension concentrate

Active substance from Table 1 to 7 | 40% ethylene glycol 10% Nonylphenol polyethylene glycol ether (15 moles of ethylene oxide) 6% Na ligninsulfonate 10% carboxymethylcellulose 1% 37% aqueous formaldehyde solution 0.2% Silicone oil in the form of a 75% aqueous emulsion 0.8%   water 32%

The finely ground active substance is intimately mixed with the additives. You get like that a suspension concentrate from which by dilution with water suspensions Any desired concentration can be produced.

2.4. Water-dispersible powder mixtures

The active ingredient is well mixed with the additives and ground well in a suitable mill. One receives spraying powders, which become with water to suspensions each dilute the desired concentration.

2.5. dusts

By intimately mixing the excipients with the active ingredient and grinding the Mixture is obtained ready to use dusts.

2.6. granules

The active ingredient is dissolved in methylene chloride, sprayed onto the carrier and the  Solvent then evaporated in vacuo. Such granules can the Cattle feed be mixed.

2.7. granules

Active substance from Table 1 to 7 | 10% Na ligninsulfonate 2% carboxymethylcellulose 1% kaolin 87%

The active ingredient is mixed with the additives, ground and treated with water moistens. This mixture is extruded and then dried in a stream of air.

2.8. granules

Active substance from Table 1 to 7 | 3% Polyethylene glycol (MG 200) 3% kaolin 94% (MW = molecular weight)

The finely ground active substance is mixed with polyethylene glycol in a mixer moistened kaolin applied evenly. In this way you get dust-free Coated granules.

2.9. Tablets or boluses

• I. Methylcellulose is stirred into water. After the material has swollen, Silica is stirred in and the mixture is suspended homogeneously. Active ingredient and  Cornstarch are mixed. In this mixture, the aqueous suspension incorporated and kneaded into a dough. The mass thus obtained is replaced by a 12 M sieve granulated and dried.
• II. All 4 excipients are mixed well.
• III. The premixes obtained according to I and II are mixed and made into tablets or Boli pressed.

2.4. Injektabiles A. Oily vehicle (slow release)

An active ingredient from Table 1 to 7 | 0.1-1.0 g Peanut oil ad 100 ml An active ingredient from Table 1 to 7 0.1-1.0 g sesame oil ad 100 ml

manufacturing

The active ingredient is stirred in a portion of the oil and optionally slightly heated, filled after cooling to the desired volume and through a suitable membrane filter sterile filtered at 0.22 microns.

B. Water-miscible solvent (average rate of release)

An active ingredient from Table 1 to 7 | 0.1-1.0 g 4-hydroxymethyl-1,3-dioxolane (glycerol formal) 40 g 1,2-propanediol ad 100 ml An active ingredient from Table 1 to 7 0,1-1,0g Glycerindimethyketal 40g 1,2-propanediol ad 100ml

manufacturing

The active ingredient is dissolved in a portion of the solvent with stirring the nominal volume is filled and sterilized by a suitable membrane filter with 0.22 μm filtered.  

C. Aqueous solubilisate (rapid release)

An active ingredient from Table 1 to 7 | 0.1-1.0 g Polyethoxylated castor oil (40 ethylene oxide units) 10g 1,2-propanediol 20 g benzyl alcohol 1g Aqua ad inject ad 100ml An active ingredient from Table 1 to 7 0.1-1.0 g Polyethoxylated sorbitan monooleate (20 ethylene oxide units) 8g 4-hydroxymethyl-1,3-dioxolane (glycerol formal) 20g benzyl alcohol 1g Aqua ad inject. ad 100ml

manufacturing

The active ingredient is dissolved in the solvents and the surfactant and with Water is filled to the nominal volume. Sterile filtration through a suitable membrane filter with 0.22 μm pore diameter.

The aqueous systems may preferably also for the oral and / or intraruminal application can be used.

3. Biological examples 3.1. Action against houseflies (Musca domestica)

A sugar cube is treated with a solution of the test substance so that the Concentration of test substance, after drying overnight, in sugar is 250 ppm. This treated cube comes with a wet cotton ball and 10 adult Musca domestica of an OP resistant strain placed on an aluminum dish, with a Beaker covered and incubated at 25 ° C. After 24 hours, the mortality rate certainly.  

The compounds of Tables 1 to 7 show a good activity against Musca domestica in this test. In particular, the compounds Nos. 1.1, 1.2 and 1.3 show an effect over 80%.

3.2. Action against Blattella germanica

In a petri dish is so much of a 0.1% acetone solution of the drug given that the amount corresponds to an application rate of 2 g / m². If the solution has evaporated, 20 Blattella germanica nymphs (last nymph stage) placed in the dish thus prepared and for 2 hours the effect of the test substance exposed. Then the nymphs are anesthetized with CO₂, in a fresh petri dish brought and kept in the dark at 25 ° C and 50 to 70% humidity. After 48 Hours, the insecticidal effect is determined by determining the kill rate.

Compounds of Tables 1 to 7 show good activity against Blattella germanica in this test. In particular, the compounds Nos. 1.1, 1.2 and 1.3 show an effect over 80%.

3.3. Example: Effect of compounds of the formula I in combination with nematodes on adult of Blatella germanica

The tests are carried out in transparent plastic containers (32 × 21.5 × 12 cm³) Air holes carried in the lids. They contain a trap, a hiding place (Egg carton), food (a small Petri dish with ground dog biscuit) and water in a jar closed with cotton. The traps consist of an upper one and a lower part, each containing agar gel as a water reservoir. The Papers with about 1 to 2 million living nematodes (Steinernema carpo capsae) on top and optionally 50 mg of a compound of formula I / m² are placed on the lower part. Above this, a wooden grid is attached to the Cockroaches offer a hiding place. The upper part is placed on the grid and both parts, upper and lower, are secured with adhesive tape.

25 male or 25 female adults (age about 4 to 6 weeks, i.e. 14 weeks including nymph development) are placed in the plastic containers and their Mortality determined after 3, 4, 5, 6 and 7 days Surviving cockroaches are removed and the test continued for another week with a new cockroach population.  

This step will be repeated until the end of the twelfth week.

Examinations with nymphs are carried out completely analogously; also investigations with mixed populations of cockroaches of different stages of development.

It turns out that compounds of formula I in combination with nematodes cockroaches fight very effectively.

Claims (27)

1. 4,5-Dicyanoimidazolderivat of formula I. characterized in that
R₁ is C₁-C₆ haloalkyl, C₁-C₆ hydroxyalkyl, C₁-C₆ dihydroxyalkyl or one of the groups
- [C₁-alkylenyl] -A₁,
- [C₁-alkylenyl] -A₂,
- [C₁-alkylenyl] -A₃,
- [C₁-alkylenyl] -A₄,
- [C₁-C₆-alkylenyl] -A₅ or
- [C₁-C₆-alkylenyl] -A₆ represents, wherein
A₁ is C₁-C₆ haloalkoxy, C₁-C₆ haloalkylthio, C₁-C₆ haloalkylsulfinyl, C₁-C₆ hydroxyalkyl, C₁-C₆ alkylcarbonyloxy, phenyl or benzdioxolyl;
A₂ is phenyl or naphthyl, each selected from one to three substituents selected from the group consisting of halogen, nitro, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-hydroxy alkyl, C₁-C₆-cyanoalkyl, C₁ -C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl, di (C₁-C₆-alkyl) amino, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbonyl, C₁-C₆ alkyl carbonyloxy and COOH are substituted;
A₃ represents a five-membered aromatic, mono- or fused bicyclic heterocycle having one to three heteroatoms selected from the series consisting of nitrogen, oxygen and sulfur, which is unsubstituted or mono- to disubstituted by halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl ; A₄ represents a five-membered non-aromatic, mono- or fused bicyclic heterocycle having one to three heteroatoms selected from the series consisting of nitrogen, oxygen and sulfur, which is unsubstituted or mono- to trisubstituted by halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl ;
A₅ represents a six-membered non-aromatic, mono- or annelated bicyclic heterocycle having one to three heteroatoms from the group consisting of nitrogen, oxygen and sulfur; which is unsubstituted or substituted by one to three substituents selected from halogen, nitro, cyano, C₁-C₆-alkyl, C₃-C₇-cycloalkyl, C₁-C₆-haloalkyl, C₁-C₆-hydroxyalkyl, C₁-C₆-cyanoalkyl, C₁- C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkyl sulfonyl, di (C₁-C₆-alkyl) amino, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylcarbonyl, C₁-C₆-alkylcarbonyloxy and COOH is substituted or monosubstituted by a substituent selected from phenyl, benzyl, benzodioxole-C₁-C₄-alkylenyl, pyridinyl, pyrimidyl or phenyl C₁-C₄-alkylenyl, wherein each of these latter substituents in the ring member in turn unsubstituted or mono- to trisubstituted by halogen, nitro, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-cyanoalkyl, C₁-C₆- Alkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-haloalkylsulfinyl, C₁-C₆- Alkylsulfonyl, C₁-C₆-dialkylamino, C₁-C₆-haloalkoxy, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylcarbonyl, C₁-C₆-alkylcarbonyloxy or COOH;
A₆ represents an unsubstituted or monosubstituted to trisubstituted aromatic, mono- or annelated bicyclic, six-membered heterocycle having one to three nitrogen atoms, wherein the substituents are independently selected from the group halogen, nitro, cyano, C₁-C₄-alkyl, C₃ -C₇-cycloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy, C₁-C₄-hydroxyalkyl, C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl, hydroxy, formyl, phenyl, pyridyl, pyrimidinyl , mono- to trisubstituted by halogen, nitro, C₁-C₃-alkyl, C₁-C₃-alkoxy, C₁-C₄-alkylcarbonyl or C₁-C₃-haloalkyl-substituted phenyl and mono- to trisubstituted by C₁-C₄-alkoxy C₁-C₄ alkyl;
R₂ is C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₃-C₇-cycloalkyl, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-haloalkylsulfinyl, hydroxy, carboxyl, halogen, nitro, cyano, amino, C₁-C₆-alkylamino, di (C₁-C₆-alkyl) amino, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylcarbonyl, C₁-C₆- Alkylcarbonylamino or C₁-C₆alkoxycarbonylamino; and
R₃ and R₄unabhangig from each other have the meaning of R₂ or hydrogen, including the physiologically contractual addition compounds. A compound according to claim 1 wherein R₁ is 3,3,3-trifluoropropyl, 2-hydroxyethyl, 2,2,2-trifluoroethoxymethyl, 2- (3,3,3-trifluoropropylthio) ethyl, 2- (trifluoromethylsulfinyl) ethyl, 3 Hydroxymethylhexyl, unsubstituted benzyl, in the phenyl moiety one to three times by fluorine, chlorine, bromine iodine, nitro, cyano, methyl, isopropyl, trifluoromethyl, methoxy, trifluoromethoxy, methylthio, 3,3,3-trifluoropropylthio, methylsulfinyl, methylsulfonyl, trifluoromethylsulfinyl, Trifluoromethylsulfonyl, hydroxymethyl, methylcarbonyloxy, methylcarbonyl, ethoxycarbonyl, -COOH or dimethylamino-substituted benzyl, stands;
R₂ is fluoro, chloro, bromo, iodo, trifluoromethyl, methoxy or trifluoromethoxy;
R₃ and R₄ independently of one another have the meaning of R₂ or stand for hydrogen; Including the physiologically acceptable addition compounds. 3. A compound of the formula I according to claim 1, wherein R₁ is - [C₁-C₆-alkylenyl] -A₃, wherein A₃ represents a five-membered aromatic, mono- or fused bicyclic heterocycle having one to three heteroatoms selected from the series nitrogen, oxygen and sulfur which is unsubstituted or mono- to disubstituted by halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl; and
R₂, R₃ and R₄ have the meanings given under formula I; including the physiologically acceptable addition compounds. 4. A compound of formula I according to claim 3, wherein
A₃ is thiazole, each of which is unsubstituted or mono- to disubstituted by halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl; and
R₂, R₃ and R₄ have the meanings given under formula I .; including the physiologically acceptable addition compounds. 5. A compound of formula I according to claim 3, wherein
A₃ is benzthiazole, each of which is unsubstituted or mono- to disubstituted by halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl; and
R₂, R₃ and R₄ have the meanings given under formula I; including the physiologically acceptable addition compounds. 6. A compound of formula I according to claim 3, wherein
A₃ is benzthiazole, each of which is unsubstituted or mono- to disubstituted by halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl; and
R₂, R₃ and R₄ have the meanings given under formula I; including the physiologically acceptable addition compounds. 7. A compound of formula I according to claim 1, wherein
R₁- represents [C₁-C₆-alkylenyl] -A₆, wherein
A₆ represents an unsubstituted or monosubstituted to trisubstituted aromatic, mono- or fused bicyclic, six-membered heterocycle having one to three nitrogen atoms, wherein the substituents are independently selected from the series fluorine, chlorine, bromine, nitro, cyano, C₁-C₃ Alkyl, C₃-C₆ cycloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkyl, C₁-C₃ haloalkoxy, C₁-C₃ hydroxyalkyl, C₁-C₃ alkylcarbonyl, C₁-C₃ alkoxycarbonyl, hydroxy, formyl, phenyl , Pyridyl, pyrimidinyl, mono- to trisubstituted by fluorine, chlorine, bromine, C₁-C₃-alkoxy, C₁-C₃-alkylcarbonyl or C₁-C₃-haloalkyl-substituted phenyl and mono- to trisubstituted by C₁-C₃-alkoxy C₁-C₃ alkyl;
R₂ is C₁-C₃ alkyl, C₁-C₃ haloalkyl, C₁-C₃ alkoxy, C₁-C₆ haloalkoxy, C₃-C₆ cycloalkyl, C₁-C₃ alkylthio, C₁-C₆ haloalkylthio, C₁-C₆ alkylsulfinyl , C₁-C₆-Haloalkylsulfinyl, hydroxy, carboxyl, halogen, nitro, cyano, amino, C₁-C₃-alkylamino, di (C₁-C₃-alkyl) amino, C₁-C₃-alkoxycarbonyl, C₁-C₃-alkylcarbonyl, C₁-C₃ Alkylcarbonylamino or C₁-C₃alkoxycarbonylamino; and
R₃ and R₄ independently have the meaning of R₂ or hydrogen; including the physiologically acceptable addition compounds. 8. A compound of formula I according to claim 7, wherein
R₁- represents [C₁-C₆-alkylenyl] -A₆, wherein
A₆ is pyridine which is unsubstituted or mono- to disubstituted by halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl; including the physiologically acceptable addition compounds. A compound of the formula I according to claim 8, wherein
R₁ represents - [C₁-C₆-alkylenyl] -A₆, wherein
A₃ is pyridine which is unsubstituted or mono- to disubstituted by fluorine chlorine, bromine, C₁-C₄-alkyl or trifluoromethyl substituted; including the physiologically acceptable addition compounds. 10. A compound of formula I according to claim 1, wherein
R₁- represents [C₁-C₃-alkylenyl] -A₁, wherein
A₁ is C₁-C₃ haloalkoxy, C₁-C₃ haloalkylthio, C₁-C₃ haloalkylsulfinyl, C₁-C₃ hydroxyalkyl, C₁-C₃ alkylcarbonyloxy, phenyl or benz dioxolyl;
R₂ is C₁-C₃ alkyl, C₁-C₃ haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₃-C₆ cycloalkyl, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, C₁-C₃ alkylsulfinyl, C₁-C₃-haloalkylsulfinyl, hydroxy, carboxyl, halogen, nitro, cyano, amino, C₁-C₃-alkylamino, di (C₁-C₃-alkyl) amino, C₁-C₃-alkoxycarbonyl, C₁-C₃-alkylcarbonyl, C₁-C₃ Alkylcarbonylamino or C₁-C₃alkoxycarbonylamino; and
R₃ and R₄ independently have the meaning of R₂ or hydrogen; including the physiologically acceptable addition compounds. 11. A compound of formula I according to claim 1, wherein
R₁- represents [C₁-C₆-alkylenyl] -A₄, wherein
A₄ represents a five-membered non-aromatic, mono- or fused bicyclic heterocycle having one to three heteroatoms selected from the series nitrogen, oxygen and sulfur, which is unsubstituted or mono- to trisubstituted by halogen, C₁-C₃-alkyl or C₁-C₃-haloalkyl ;
R₂ is C₁-C₃ alkyl, C₁-C₃ haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₃-C₆ cycloalkyl, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, C₁-C₃ alkylsulfinyl, C₁-C₃-haloalkylsulfinyl, hydroxy, carboxyl, halogen, nitro, cyano, amino, C₁-C₃-alkylamino, di (C₁-C₃-alkyl) amino, C₁-C₃-alkoxycarbonyl, C₁-C₃-alkylcarbonyl, C₁-C₃- Alkylcarbonylamino or C₁-C₃alkoxycarbonylamino; and
R₃ and R₄ independently have the meaning of R₂ or hydrogen; including the physiologically acceptable addition compounds. 12. A compound of formula I according to claim 1, wherein
R₁- represents [C₁-C₆-alkylenyl] -A₅, wherein
A₅ represents a six-membered non-aromatic, mono- or annelated bicyclic heterocycle having one to three heteroatoms from the group consisting of nitrogen, oxygen and sulfur; which is unsubstituted or substituted by one to three substituents selected from fluorine, chlorine, bromine, nitro, cyano, C₁-C₃-alkyl, C₃-C₆-cycloalkyl, C₁-C₃-haloalkyl, C₁-C₃-hydroxyalkyl, C₁-C₃ Cyanoalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, C₁-C₃ alkylsulfinyl, C₁-C₃ haloalkylsulfinyl, C₁-C₃ alkylsulfonyl, di (C₁-C₃ -alkyl) amino, C₁-C₃-alkoxycarbonyl, C₁-C₃-alkyl carbonyl, C₁-C₃-alkylcarbonyloxy and COOH or is monosubstituted by a substituent selected from the group phenyl, benzyl, benzo-C₁-C₃-alkylenyl, pyridinyl , Pyrimidyl or phenyl-C₁-C₃-alkylenyl, wherein each of these latter substituents in the ring member in turn unsubstituted or mono- to trisubstituted by halogen, nitro, cyano, C₁-C₃-alkyl, C₁-C₃-haloalkyl, C₁-C₃-cyanoalkyl, C₁-C₃-alkoxy, C₁-C₃-alkylthio, C₁-C₃-haloalkylthio, C₁-C₃-alkylsulfinyl, C₁-C₃-haloalkylsulfine yl, C₁-C₃ alkylsulfonyl, C₁-C₃ dialkylamino, C₁-C₃ haloalkoxy, C₁-C₃ alkoxycarbonyl, C₁-C₃ alkylcarbonyl, C₁-C₃ alkylcarbonyloxy or COOH;
R₂ is C₁-C₃ alkyl, C₁-C₃ haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₃-C₆ cycloalkyl, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, C₁-C₃ alkylsulfinyl, C₁-C₃-haloalkylsulfinyl, hydroxy, carboxyl, halogen, nitro, cyano, amino, C₁-C₃-alkylamino, di (C₁-C₃-alkyl) amino, C₁-C₃-alkoxycarbonyl, C₁-C₃-alkylcarbonyl, C₁-C₃- Alkylcarbonylamino or C₁-C₃alkoxycarbonylamino; and
R₃ and R₄ independently have the meaning of R₂ or hydrogen; including the physiologically acceptable addition compounds. 13. A compound of the formula I according to claim 1, selected from the series:

• - 1 - [(2,6-dibromopyridin-5-yl) methyl] -2 - [(2,6-dichloro-4-trifluoromethyl) -phenyl] -4,5-dicyano-1H-imidazole;
• - 1 - [(2-chlorothiazol-4-yl) methyl] -2 - [(2,6-dichloro-4-trifluoromethyl) phen-yl] -4,5-dicyano-1H-imidazole;
• - 1 - [(2-chloropyridin-5-yl) methyl] -2 - [(2,6-dichloro-4-trifluoromethyl) phenyl] - 4,5-dicyano-1H-imidazole;
• - 1- (3,5-Ditrifluoromethylbenzyl) -2 - [(2,6-dichloro-4-trifluoromethyl) phen-yl] -4,5-dicyano-1H-imidazole;
• - 1- (N-piperidylethylenyl) -2 - [(2,6-dichloro-4-trifluoromethyl) phenyl] -4,5-dicyano-1H-imidazole;
• - 1- (N -morpholinylethylenyl) -2 - [(2,6-dichloro-4-trifluoromethyl) phenyl] -4,5-dicyano-1H-imidazole;
• - 1 - [(2-chlorothiazol-4-yl) methyl] -2- [2,6-dichlorophenyl] -4,5-dicyano-1H-imidazole;
• - 1 - [(2-chloropyridin-5-yl) methyl] -2- [2-chlorophenyl] -4,5-dicyano-1H-imidazole;

each including their physiologically acceptable addition compounds. 14. A process for preparing a compound of the formula I according to claim I, characterized in that a compound of the formula II wherein the substituents R₁, R₂, R₃ and R₄ have the meanings given under formula I cyclized with a suitable oxidizing agent, preferably starting from a compound of formula II, wherein instead of R₁ is hydrogen, so that first a compound of formula I is formed, wherein instead of R₁ is also hydrogen, and introducing a R₁ given at rest, which has a different meaning from hydrogen, subsequently in the sense of an N-alkylation reaction. 15. means for controlling noxious insects, preferably cockroaches or flies, characterized in that it is in addition to at least one usual for pesticides A formulation adjuvant is a 4,5-dicyanoimidazole of the formula I according to one of the claims 1 to 13 contains. 16. Anthelmintikum, characterized in that in addition to at least one physio logically compatible formulation auxiliary a 4,5-Dicyanoimidazol of formula I after one of claims 1 to 13 contains. 17. Method for controlling insects, preferably cockroaches or flies,  characterized in that the pests or their habitat with a effective amount of a 4,5-Dicyanoimidazols of formula I according to any one of claims I treated until 13. 18. A method for combating helminths in warm-blooded animals, characterized gekennzeich net, that an anthelmintic active amount of a 4,5-Dicyanoimidazols of the formula I. according to any one of claims 1 to 13 administered to the host animal. 19. Use of a 4,5-Dicyanoimidazols of the formula I according to any one of claims 1 to 13 for the control of insects or for the control of helminths in warm blooded animals. 20. 4,5-dicyanoimidazole of the formula I according to any one of claims 1 to 13 for use in a method of combating helminths in warm-blooded animals. 21. Use of a 4,5-Dicyanoimidazols of the formula I according to any one of claims 1 to 13 for the preparation of a pharmaceutical, preferably an anthelmintic. 22. Method for controlling insects, in particular cockroaches or flies, characterized in that the pests simultaneously with a schabentötenden Amount of cockroach pathogenic nematodes and an effective amount of a compound of Formula I according to any one of claims 1 to 5 brings into contact. 23. The method according to claim 22, characterized in that the nematodes immobilized on a suitable sheetlike, absorbent substrate and onto this support an active ingredient of the formula I according to one of claims 1 to 13 applies. 24. The method according to claim 22, characterized in that a compound of the formula I according to any one of claims 1 to 13 in a concentration of 5 mg to 500 mg active substance / m² together with living cockroach pathogenic nematodes on a substrate up wearing. 25. The method according to claim 22, characterized in that a compound of the formula I according to any one of claims 1 to 5 in a concentration of 10 mg to 50 mg / m² is applied to the substrate.   26. Cockroach trap with a substrate on the living, cockroach pathogenic nematodes are immobilized, characterized in that the substrate 5 mg to 500 mg of a connection of the formula I according to one of claims 1 to 5 per m².