DE19544799A1 - New 3-poly:substituted anilino-pyrazole derivatives - Google Patents

Abstract

5-(Tetra- or penta-substituted anilino)-pyrazole derivatives of formula (I) are new. Ar = tetra-substituted phenyl (where o-nitro is excluded as substituent) or penta-substituted phenyl; R1 = H or (all optionally substituted) alkyl, alkenyl, alkynyl, aryl, aralkyl or heteroaryl; R2,R3 = H, halogen, CN or NO2; alkyl, aryl or heteroaryl (all optionally substituted); or COOR5, CONR6R7 or S(O)nR8; R4 = H; alkyl, alkenyl, alkynyl, aralkyl, aryloxy or aralkoxy (all optionally substituted); or SO2NR6R7, SO2R9, COR10, CH2N(R9)COOR5 or CH2N(R9)SO2R5; R5 = alkyl; R6, R7 = H or alkyl, or together form a ring (optionally containing one or more further heteroatom(s)); R8 = alkyl or haloalkyl; R9 = alkyl, alkoxy or (both optionally substituted) aryl or aryloxy; and n = 0-2.

Description

The present invention relates to new substituted 5-aminopyrazoles, processes for their manufacture and their use as pesticides.

It is known that certain substituted 5-phenylaminopyrazoles are insecticidal Have properties (see, for example, WO-A 93/19 054 or WO-A 95/22 530). The effectiveness of these compounds, however, is particularly low substance concentrations and application rates, not always completely satisfactory.

New substituted 5-aminopyrazoles of the formula (I) have been found

in which
Ar stands for tetrasubstituted phenyl, whereby o-nitro is excluded as a substituent, or stands for pentasubstituted phenyl,
R¹ represents hydrogen or represents optionally substituted alkyl, alkenyl, alkynyl, aryl, aralkyl or hetaryl,
R² and R³ independently of one another represent hydrogen, halogen, cyano, nitro, in each case optionally substituted alkyl, aryl or hetaryl or one of the residues CO₂R⁵, CONR⁶R⁷ or S (O) nR⁸ and
R⁴ represents hydrogen, in each case optionally substituted alkyl, alkenyl, alkynyl, aralkyl, aryloxy or aralkyloxy or one of the radicals SO₂NR⁶R⁷, SO₂R⁹, COR¹⁰, CH₂N (R⁹) CO₂R⁵ or CH₂N (R⁹) SO₂R⁵, where
R⁵ represents alkyl,
R⁶ and R⁷ independently of one another represent hydrogen or alkyl or together with the N atom to which they are attached form a ring which optionally contains one or more further heteroatoms,
R⁸ represents alkyl or haloalkyl,
R⁹ represents alkyl or optionally substituted aryl,
R¹⁰ stands for alkyl, alkoxy or for optionally substituted aryl or aryloxy and
n stands for 0, 1 or 2.

It was also found that one

• a) the substituted 5-aminopyrazoles of the formula (I) are obtained if 5-aminopyrazoles of the formula (II) in which
  R¹, R² and R³ have the meaning given above,
  with compounds of the formula (III) Hal-Ar (III) in which
  Ar has the meaning given above and
  Hal stands for halogen,
  in the presence of an acid acceptor and in the presence of a diluent
  and optionally the compounds of formula (Ia) thus obtained in which
  Ar, R¹, R² and R³ have the meaning given above,
  with compounds of the formula (IV) ER ^4-1 (IV) in which
  R ^{4-1 has} the meaning given above for R mit with the exception of hydrogen and
  E represents an anionic leaving group,
  in the presence of an acid acceptor and optionally in the presence of a diluent;
  or
• b) substituted 5-aminopyrazoles of the formula (Ib) in which
  Ar, R¹, R², R³ and R ^{4-1 have} the meaning given above, is obtained if 5-aminopyrazoles of the formula (II) in which
  R¹, R² and R³ have the meaning given above,
  with compounds of the formula (IV) ER ^4-1 (IV) in which
  E and R ^{4-1 have} the meaning given above, in the presence of an acid acceptor and in the presence of a diluent, and the compounds of the formula (V) thus obtained in which
  R¹, R², R³ and R ^{4-1 have} the meaning given above,
  then with compounds of the formula (III) Hal-Ar (III) in which
  Ar and Hal have the meaning given above,
  in the presence of an acid acceptor and in the presence of a diluent.

Finally it was found that the new substituted 5-aminopyrazoles of Formula (I) have strong biological properties and especially for Control of animal pests, especially insects, arachnids and nematodes, which are used in agriculture, in forests, in supplies and materials protection as well as in the hygiene sector.

The substituted 5-aminopyrazoles according to the invention are represented by the formula (I) generally defined.

Preferred substituents or ranges of the radicals listed in the formulas mentioned above and below are explained below:
Ar is preferably four or five times, identical or different from halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₆-haloalkyl, C₁-C₄-alkoxy, C₁-C₆-haloalkoxy, C₁-C₄-alkylthio, C₁- C₆-Haloalkylthio, C₁-C₆-Ha logenalkylsulfinyl or C₁-C₆-haloalkylsulfonyl substituted phenyl, where in the case of quadruple substitution no nitro group may be in the o-position.

R¹ preferably represents hydrogen, C₁-C₈-alkyl, C₁-C₈-haloalkyl, C₁-C₈- Hydroxyalkyl, C₁-C₄-alkoxy-C₁-C₅-alkyl, for each optionally one  fold to triple, identical or different by halogen, C₁-C₄-alkyl, C₁- C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-haloal kylthio, CN or NO₂ substituted phenyl or benzyl, for single to triple, if necessary, the same or different Halogen, C₁-C₄-alkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkyl substituted tes pyridyl or, for each, if appropriate, once or twice the same or different from halogen, C₁-C₄-alkyl, C₁-C₄-alkoxy or C₁-C₄- Haloalkyl substituted pyrimidyl, thiadiazolyl or thiazolyl.

R² and R³ independently of one another preferably represent hydrogen, halogen, Cyano, nitro, C₁-C₅-alkyl, C₁-C₈-haloalkyl, C₁-C₈-hydroxyalkyl, for each through single to triple, the same or different Halogen, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkyl or C₁-C₄-Ha logenalkylthio substituted phenyl or thienyl or for one of the radicals CO₂R⁵, CONR⁶R⁷ or S (O) nR⁵.

R⁴ preferably represents hydrogen, C₁-C₈-alkyl, C₁-C₅-haloalkyl, C₁-C₈- Hydroxyalkyl, C₁-C₄-alkoxy-C₁-C₅-alkyl, C₃-C₅-alkenyl, C₃-C₅-halogen alkenyl, C₃-C₈-hydroxyalkenyl, C₁-C₄-alkoxy-C₃-C₅-alkenyl, C₃-C₅-alkali nyl, C₃-C₈-haloalkynyl, C₃-C₈-hydroxyalkynyl, C₁-C₄-alkoxy-C₃-C₈ alkynyl, each optionally up to triple, the same or ver distinguished by halogen, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkyl or C₁-C₄ haloalkoxy substituted phenoxy, benzyl or benzyloxy or for one of the radicals SO₂NR⁶R⁷, SO₂R⁹, COR¹⁰, CH₂N (R⁹) CO₂R⁵ or CH₂N (R⁹) SO₂R⁵.

R⁵ is preferably C₁-C₈ alkyl.

R⁶ and R⁷ independently of one another preferably represent hydrogen-C₁-C₈-alkyl or together with the N atom to which they are attached for a 5- to 7-membered ring, optionally up to two additional hetero contains atoms from the series N, O and S.

R⁸ is preferably C₁-C₈-alkyl or C₁-C₈-haloalkyl.  

R⁹ is preferably C₁-C₈ alkyl or optionally up to three fold, the same or different by halogen, C₁-C₄-alkyl or C₁-C₄-alk oxy substituted phenyl.

R¹⁰ preferably represents C₁-C₅-alkyl, C₁-C₈-alkoxy or any given if single to triple, identical or different by halogen, C₁-C₄- Alkyl or C₁-C₄ alkoxy substituted phenyl or phenoxy.

n is preferably 0, 1 or 2.

Ar particularly preferably stands for four or five times, the same or ver distinguished by fluorine, chlorine, bromine, cyano, nitro, C₁-C₂-alkyl, C₁-C₂-alk oxy, C₁-C₂-alkylthio or C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy, C₁- C₄-haloalkylthio, C₁-C₄-haloalkylsulfinyl or C₁-C₄-haloalkyl sulfonyl, each with 1 to 7 identical or different halogen atoms from the series fluorine, chlorine and bromine substituted phenyl, in which case the quadruple substitution must not have a nitro group in the o-position.

R¹ particularly preferably represents C₁-C₆-alkyl, C₁-C₆-haloalkyl with one to three identical or different halogen atoms from the fluorine series.

Chlorine and bromine, C₁-C₆-hydroxyalkyl, C₁-C₂-alkoxy-C₁-C₆-alkyl, for possibly up to three times the same or different Fluorine, chlorine, bromine, C₁-C₃-alkyl, C₁-C₃-alkoxy, C₁-C₃-haloalkyl, C₁- C₃-haloalkoxy or C₁-C₄-haloalkylthio, each with one to three same or different halogen atoms from the series fluorine, chlorine and bromine, CN or nitro substituted phenyl, for optionally simple up to three times, identical or different, by fluorine, chlorine, bromine, C₁-C₃- Alkyl, C₁-C₃-alkoxy or C₁-C₃-haloalkyl with one to three of the same or various halogen atoms from the series fluorine, chlorine and bromine substituted pyridyl or for each, if necessary, once or twice the same or different by fluorine, chlorine, bromine, C₁-C₃-alkyl, C₁-C₃-alkoxy or C₁-C₃-halo genalkyl with one to three identical or different halogen atoms the series fluorine, chlorine and bromine substituted pyrimidyl or thia diazolyl.  

R² and R³ independently of one another are particularly preferably hydrogen Fluorine, chlorine, bromine, cyano, C₁-C₆ haloalkyl with one to six of the same or various halogen atoms from the series fluorine, chlorine and bromine, for each, if necessary, up to three times the same or different substituted by fluorine, chlorine, bromine, C₁-C₃-alkyl or C₁-C₃-alkoxy Phenyl or thienyl or for one of the residues CO₂R⁵, CONR⁶R⁷ or S (O) nR⁸.

R⁴ particularly preferably represents hydrogen, in each case if appropriate one to three halogen atoms from the series fluorine, chlorine, bromine substituted C₁-C₆-alkyl, C₃-C₆-alkenyl or C₃-C₆-alkynyl, C₁-C₄-alkoxymethyl, for each optionally single or double, the same or different benzyl or benzyloxy substituted by fluorine, chlorine or bromine or for one of the radicals SO₂R⁹, COR¹⁰ or CH₂N (R⁹) CO₂R⁵.

R⁵ is particularly preferably C₁-C₄ alkyl.

R⁶ and R⁷ independently of one another are particularly preferably hydrogen Methyl or ethyl.

R⁸ is particularly preferably a C₁-C₄-alkyl or C₁-C₄-haloalkyl up to three halogen atoms from the fluorine and chlorine series.

R⁹ particularly preferably represents C₁-C₄-alkyl or optionally simple up to three times the same or different by fluorine, chlorine or bromine sub substituted phenyl.

R¹⁰ particularly preferably represents C₁-C₄ alkyl or optionally simple up to three times the same or different by fluorine, chlorine or bromine sub substituted phenyl.

n particularly preferably represents 0, 1 or 2.

Ar very particularly preferably stands for four or five times, the same or ver separated by fluorine, chlorine, bromine, cyano, nitro, trifluoromethyl, trifluor methoxy, trifluoromethylthio or trifluoromethylsulfonyl substituted Phe  nyl, whereby in the case of quadruple substitution no nitro group in o- Position.

R¹ very particularly preferably represents methyl, ethyl, n- or i-propyl, n- Butyl, t-butyl, or for optionally single to triple, the same or different from fluorine, chlorine, bromine, CF₃, OCF₃, SCF₃, CN or NO₂ substituted phenyl.

R² and R³ independently of one another very particularly preferably represent chlorine, Bromine, cyano, trifluoromethyl or pentafluoroethyl, for optionally one times to three times, the same or different from fluorine, chlorine, bromine, Me thyl or methoxy substituted phenyl or for one of the residues CO₂R⁵, CONR⁶R⁷ or S (O) nR⁸.

R⁴ very particularly preferably represents hydrogen methyl, ethyl, 2-propenyl, 2-propynyl, methoxymethyl, ethoxymethyl, propoxymethyl, i-propoxyme ethyl, n-butoxymethyl.

R⁵ very particularly preferably represents methyl or ethyl.

R⁶ and R⁷ are very particularly preferably hydrogen.

R⁸ very particularly preferably represents methyl, ethyl, trifluoromethyl, 1,1-di fluoroethyl or 2,2,2-trifluoroethyl.

n very particularly preferably represents 0, 1 or 2.

The residue definitions listed above or in preferred areas or explanations apply to the end products and to the initial and intermediate products accordingly. These residual definitions can be among themselves, that is can also be combined as desired between the respective preferred areas.

According to the invention, preference is given to the compounds of the formula (I) in which a combination of the Be listed as preferred (preferred) interpretations are available.  

According to the invention, particular preference is given to the compounds of the formula (I), in which are a combination of those listed as particularly preferred above Meanings exist.

The compounds of the formula are very particularly preferred according to the invention (I) in which a combination of the above is particularly preferred listed meanings is present.

In the residue definitions listed above and below are hydrocarbons residues such as alkyl or alkenyl - also in compounds with heteroatoms such as Alkoxy or Alylthio - if possible straight or branched.

In addition to the preparation examples, the compounds according to FIG the following table 1:

Table I

For example, 5-amino-1-t-butyl-3,4-dicyano-pyrazole, 1,3,5-tri is used chloro-2,4,6-trifluorobenzene and chloromethyl ethyl ether as starting materials, so can the course of the reaction of the method (a) according to the invention by the following Formula scheme are reproduced:

For example, 5-amino-1-t-butyl-3,4-dicyano-pyrazole, iodomethane is used and 1,3,5-trichloro-2,4,6-trifluorobenzene as starting materials, so the reaction Sequence of process (b) according to the invention using the following formula are reproduced:

The starting point for carrying out processes (a) and (b) according to the invention 5-Amino-pyrazoles to be used are general by the formula (II) Are defined. The 5-aminopyrazoles of the formula (II) are known and / or can be found in Analogy to known methods can be produced (see, for example, Chem. Het. Comp. 17 (1981), 1; J. Org. Chem. 21 (1956); EP 0 201 852; EP 0 392 241; Chem. Ber.  95: 2871 (1962); J. Org. Chem. 29 (1964) 1915; Isv. Attad. Nauk SSR, Ser. Khim 11 (1990) 2583; J. Chem. Research (5), 1993, 76).

The also in the process (a) and (b) according to the invention as a starting point Compounds to be used are generally defi by the formula (III) kidney. Hal preferably represents fluorine, chlorine or bromine, particularly preferably Fluorine or chlorine.

The compounds of formula (III) are known and / or can be analogous to known processes can be prepared (see, for example, EP 120 575; J. Fluorine Chem. 1991, 53, 33; Zh. Vses. Khim. Obshchest. 1969, 14, 114 [CA 70: 114726]).

The starting point in process (a) and (b) according to the invention Compounds to be used are generally defi by the formula (IV) kidney.

E preferably represents chlorine, bromine, iodine, acetoxy, tosyl or mesyl.

The compounds of formula (IV) are generally known substances of the organization African chemistry.

The processes (a) and (b) according to the invention are preferably carried out under Ver using diluents. Come as a diluent practically all inert organic solvents in question. These include preferential wise aliphatic and aromatic, optionally halogenated hydrocarbons fe such as pentane, hexane, heptane, cyclohexane, petroleum ether, gasoline, ligroin, benzene, Toluene, xylene, methylene chloride, ethylene chloride, chloroform, carbon tetrachloride, Chlorobenzene and o-dichlorobenzene, ethers such as diethyl and dibutyl ether, glycol dimethyl ether and diglycol dimethyl ether, tetrahydrofuran and dioxane, ketones such as acetone, methyl ethyl, methyl isopropyl or methyl isobutyl ketone, esters such as methyl acetate or ethyl ester, nitriles such. B. acetonitrile or pro pionitrile, amides such as e.g. B. dimethylformamide, dimethylacetamide and N-methyl pyrrolidone and dimethyl sulfoxide, tetramethylene sulfone or hexamethylenephos phosphoric triamide.

All of them can be used as acid acceptors in processes (a) and (b) according to the invention Acid binder which can usually be used for such reactions  be set. Alkali metal and alkaline earth metal are preferred hydrides, such as lithium, sodium, potassium or calcium hydride, alkali metal or Alkaline earth metal hydroxides, such as lithium, sodium, potassium or calcium hydroxide, Alkali metal or alkaline earth metal carbonates or bicarbonates, such as Na trium or potassium carbonates or hydrogen carbonate or calcium carbonate, Alkali metal acetates, such as sodium or potassium acetate, alkali metal alcoholates, such as Sodium or potassium tert. -butylate, also basic nitrogen compounds, such as Trimethylamine, triethylamine, tripropylamine, tributylamine, diisobutylamine, di cyclohexylamine, ethyldiisopropylamine, ethyldicyclohexylamine, N, N-dimethylbene cylamine, N, N-dimethyl-aniline, pyridine, 2-methyl, 3-methyl, 4-methyl, 2,4-di methyl, 2,6-dimethyl, 2-ethyl, 4-ethyl and 5-ethyl-2-methyl-pyridine, 1,5-di azabicyclo [4,3,0] non-5-ene (DBN), 1,8-diazabicydo- [5,4,0] undec-7-ene (DBU) or 1,4-diazabicyclo [2,2,2] octane (DABCO).

The reaction temperatures in process (a) and (b) can be varied over a wide range. Generally one works at Temperatures between 0 ° C and 100 ° C, preferably at temperatures between 10 ° C and 80 ° C.

Processes (a) and (b) according to the invention are generally described under Nor painting done. However, it is also possible to increase or decrease pressure to work.

To carry out processes (a) and (b) according to the invention, the respective because starting materials are generally required in approximately equimolar amounts gene used. However, it is also possible to use either of the two To use components in a larger excess. The reactions who generally in a suitable diluent in the presence of a Acid acceptor performed, and the reaction mixture is at several hours the required temperature is stirred. The processing takes place at the The methods according to the invention in each case by customary methods (cf. the manufacturer examples).

The compounds of the formula (Ia) can also be obtained by reacting 5- Halogenpyrazoles with appropriately substituted anilines. The necessary for this 5-halopyrazoles are, for example, from the pyrazoles of the formula (II) Diazotization and subsequent Sandmeyer reaction accessible, while substi  Anilines are known in large numbers and are often commercially available or easy to manufacture are, for example by reducing corresponding nitro compounds.

The active ingredients are suitable for good plant tolerance and inexpensive warmth blood toxicity to control animal pests, especially insects, Arachnids and nematodes found in agriculture, in forests, in and material protection as well as in the hygiene sector. You can before are preferably used as pesticides. You are against normal sensitive and resistant species as well as against all or individual stages of development effective. The pests mentioned above include:

From the order of the Isopoda z. B. Oniscus asellus, Armadillidium vulgare, Por cellio 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. 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 lectuiarius, Rhodnius prolixus, Triatoma spp.

From the order of Homoptera z. B. Aleurodes brassicae, Bemisia tabaci, Tri aleurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigus spp., Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp.

From the order of the Lepidoptera z. B. Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella 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, Spodoptera litura, Spodoptera spp., Trichoplusiani, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinea pellionella, Hofmannophila pseudospretella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana.

From the order of the Coleoptera z. B. Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica.

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

From the order of the Diptera z. B. Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa.

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., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp.

The plant parasitic nematodes include z. B. Pratylenchus spp., Radopho lus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphi nema spp., Trichodorus spp.

The compounds of the formula (I) according to the invention are particularly noteworthy with a high level of insecticidal and acaricidal activity.

They can be used with particularly good success to combat plant damage insects, such as against the horseradish leaf beetle larvae (Phae don cochlaeriae), the caterpillars of the cockroach (Plutella maculipennis), the green one Rice leafhopper (Nephotettix cinctriceps) and the caterpillars of the owl butterfly (Spodoptera frugiperda) or for combating plant-damaging mites, such as wise against the common spider mite (Tetranychus urticae).

The active ingredients can be converted into the usual formulations, such as Lö solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, sol Liche powders, granules, suspension emulsion concentrates, impregnated with active ingredients natural and synthetic substances as well as very fine encapsulations in polymeric substances fen.  

These formulations are prepared in a known manner, e.g. B. by Ver mixing the active ingredients with extenders, i.e. liquid solvents and / or solid carriers, optionally using surface-active agents Agents, that is emulsifiers and / or dispersants and / or foam generators resources.

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 alkylnaph thalines, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as Chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons fe, such as cyclohexane or paraffins, e.g. B. petroleum fractions, mineral and vegetable Liche oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly po lare solvents, such as dimethylformamide and dimethyl sulfoxide, and water.

The following are suitable as solid carriers:
e.g. B. ammonium salts and natural rock powders such as kaolins, clays, talcum, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as finely divided silica, aluminum oxide and silicates, as solid carriers for granules are possible: 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 stalks; 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.

Adhesives such as carboxymethyl cellulose, natural, can be used in the formulations Liche and synthetic powdery, granular or latex-shaped polymers used such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural Phospholipids such as cephalins and lecithins and synthetic phospholipids. Wei 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 phthalalo cyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, Cobalt, molybdenum and zinc can be used.

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

The active ingredient according to the invention can be present in its commercially available formulations and in the use forms prepared from these formulations in admixture with other active ingredients, such as insecticides, attractants, sterilants, Bak tericides, acaricides, nematicides, fungicides, growth-regulating substances or herbicides. The insecticides include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, chlorinated hydrocarbons, phenyl ureas, 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-cyanophenoxy) 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, Binapacryl, Biphenyl, Bitertanol, Blasticidin-S, Bromuconazole, Bupirimate, Buthiobate,
Calcium polysulfide, captafol, captan, carbendazim, carboxin, quinomethionate (quinomethionate), 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, Fen propimorph, Fentinacetat, Fentinhydroxyd, Ferbam, Ferimzone, Fluazinam, Fludioxonil, Fluoromide, Fluquinconazole, Flusilazole, Flusulfamide, Flutolanyl, Futuberolosil, Futuberfosil , Furme cyclox,
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, pyroquilon,
Quintozen (PCNB),
Sulfur and sulfur preparations,
Tebuconazole, tecloftalam, tecnazene, tetraconazole, thiabendazole, Thicyofen, thiophanate-methyl, thiram, Tolclophos-methyl, tolylfluanid, triadimefon, Triadi menol, triazoxide, Trichlamid, tricyclazole, tridemorph, triflumizole, triforine, triticonazole,
Validamycin A, vinclozolin,
Zineb, ziram.

Bactericides:
Bronopol, dichlorophene, nitrapyrin, nickel dimethyldithiocarbamate, Kasugamy cin, octhilinone, furan carboxylic acid, oxytetracycline, probenazole, streptomycin, tecloftalam, copper sulfate and other copper preparations.

Insecticides / acaricides / nematicides:
Abamectin, AC 303 630, Acephat, Acrinathrin, Alanycarb, Aldicarb, Alpha methrin, Amitraz, Avermectin, AZ 60541, Azadirachtin, Azinphos A, Azinphos M, Azocyclotin,
Bacillus thuringiensis, Bendiocarb, Benfuracarb, Bensultap, Betacyfluthrin, Bifen thrin, BPMC, Brofenprox, Bromophos A, Bufencarb, Buprofezin, Butocarboxin, Butylpyridaben,
Cadusafos, Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, CGA 157 419, CGA 184699, Chloethocarb, Chlorethoxyfos, Chlorfenvinphos, Chlor fluazuron, Chlormephos, Chlorpyrifos, Chlorpyrifos M, Cis-Resmethrin, Clocy thrin, Chrinophhrin, Clophin Cyhalothrin, cyhexatin, cypermethrin, cyromazine,
Deltamethrin, Demeton M, Demeton S, Demeton-S-methyl, Diafenthiuron, Di azinon, Dichlofenthion, Dichlorvos, Dicliphos, Dicrotophos, Diethion, Diflubenzu ron, Dimethoat, Dimethylvinphos, Dioxathion, Disulfoton,
Edifenphos, Emamectin, Esfenvalerat, Ethiofencarb, Ethion, Ethofenprox, Etho prophos, Etrimphos,
Fenamiphos, Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate, Fipro nil, Fluazinam, Flucycloxuron, Flucythrinat, Flufenoxuron, Fufionatexfonophon, Fufionproxophon, Fufonproxophone, Fufonproxophon, Fufonproxophon, Fufonfox, Fufionfox, Fufionfox, Fufone
HCH, heptenophos, hexaflumuron, hexythiazox,
Imidacloprid, Iprobefos, Isazophos, Isofenphos, Isoprocarb, Isoxathion, Iver mectin, Lambda-cyhalothrin, Lufenuron,
Malathion, Mecarbam, Mervinphos, Mesulfenphos, Metaldehyde, Methacrifos, Methamidophos, Methidathion, Methiocarb, Methomyl, Metolcarb, Milbemectin, Monocrotophos, Moxidectin,
Naled, NC 184, NI 25, Nitenpyram,
Omethoate, Oxamyl, Oxydemethon M, Oxydeprofos,
Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos M, Pirimiphos A, Profenofos, Promecarb, Propaphos, Propoxur, Prothiofos, Prothoat, Pymetrozin, Pyrachlophhine, Pyrachlophhion, Pyrachlophion, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophion Pyridaben, pyrimidifen, pyriproxifen,
Quinalphos,
RH 5992,
Salithion, Sebufos, Silafluofen, Sulfotep, Sulprofos,
Tebufenozid, Tebufenpyrad, Tebupirimphos, Teflubenzuron, Tefluthrin, Temephos, Terbam, Terbufos, Tetrachlorvinphos, Thiafenox, Thiodicarb, Thiofanox, Thio methon, Thionazin, Thuringiensin, Tralomichonon, Triaromenontron, Triaromenontron, Triarathenlarbon, Triarathenltronium, Triarathenltronium, Triarathenltronium, Triarathenltronium, Triarathenltronium, Triarathenltronium, Triaromenontrin, Triarathenltronium, Triaromenontrin, Triarathenltron, Triaromenontron
Vamidothione, XMC, xylylcarb, YI 5301/5302, zetamethrin.

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

The active compounds according to the invention can also be used in their 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 range from 0.0000001 to 95% by weight of active ingredient preferably between 0.0001 and 1 wt .-%.

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

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

Pediculus spp., Phtirus spp., Solenopotes spp.

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

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

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

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

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

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

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

The active compounds of the formula (I) according to the invention are also suitable for loading fighting arthropods that farm livestock, such as B. cattle, Sheep, goats, horses, pigs, donkeys, camels, buffaloes, rabbits, chickens, Turkeys, ducks, geese, bees, other pets such as B. Dogs, cats, parlors birds, aquarium fish and so-called experimental animals, such as B. hamster, sea pigs, rats and mice. By fighting this arthro deaths and reduced performance (for meat, milk, wool, Hides, eggs, honey, etc.) can be reduced, so that by using the Active ingredients according to the invention a more economical and easier animal husbandry is possible.

The active compounds according to the invention are used in the veterinary sector in a known manner by enteral administration in the form of, for example, Ta Bletten, capsules, watering, drenching, granules, pastes, boluses, the feed-through Method, of suppositories, by parenteral administration, such as by injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), Implan tate, by nasal application, by dermal application in the form, for example of diving or bathing (dipping), spraying (spray), pouring on (pour-on and  Spot-on), washing, powdering and with the help of active ingredients Shaped bodies, such as collars, ear tags, tail tags, limb straps, Halters, marking devices etc.

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

It has also been found that the compounds of the formula (I) show a high insecticidal activity against insects, the technical materia destroy lien.

The following insects may be mentioned by way of example and preferably, but without limitation:
Beetle like
Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Ptilinus pecticornis, Dendrobium pertinex, Ernobius mollis, Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctus planicollis, Lyctus linearesces rugus, Lyctus pubescescus, Lyctus pubis linearis, Lyctus linearesces rug Xyleborus spec. Tryptodendron spec. Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec. Dinoderus minutus.

Skin wings like
Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur.

Termites like
Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus.

Bristle tails
like Lepisma saccarina.

In the present context, technical materials include non-living ones To understand materials, such as preferably plastics, adhesives, glues, Pa paper and cardboard, leather, wood and wood processing products and paints.

It is particularly preferred to protect against insect attack the material around wood and wood processing products.

Among wood and wood processing products, which by the invention Agents or mixtures containing them can be protected is exemplary to understand: timber, wooden beams, railway sleepers, bridge parts, jetties, Wooden vehicles, boxes, pallets, containers, telephone poles, wooden panels, Wooden windows and doors, plywood, chipboard, carpentry or wood products te that are used in general in house construction or in joinery the.

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

The formulations mentioned can be prepared in a manner known per se be, e.g. B. by mixing the active ingredients with at least one Lö solvent or diluent, emulsifier, dispersing and / or binding or fixing agent tels, water repellants, possibly desiccants and UV stabilizers and opp if necessary dyes and pigments and other processing aids.

The insecticidal agents used to protect wood and wood-based materials or concentrates contain the active ingredient according to the invention in a concentra tration from 0.0001 to 95 wt .-%, in particular 0.001 to 60 wt .-%.

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

An organic chemical solvent serves as the solvent and / or diluent solvent or solvent mixture and / or an oily or oily heavy  volatile organic chemical solvent or solvent mixture and / or a polar organic chemical solvent or solvent mixture and / or water and optionally an emulsifier and / or wetting agent.

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

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

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

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

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

As an organic chemical binder in the present Er finding the known water-dilutable and / or in the used organic chemical solvents soluble or dispersing or emulsifying Resins and / or binding drying oils, especially binders consisting of or containing an acrylic resin, a vinyl resin, e.g. B. polyvinyl acetate, Polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as indene Coumarone resin, silicone resin, drying vegetable and / or drying oils and / or physically drying binders based on a natural and / or Resin used.

The synthetic resin used as a binder can be in the form of an emulsion, disper sion or solution. Bitumen or bituminous substances up to 10 wt .-%, are used. In addition, you can dyes, pigments, water-repellants, odor correctors known per se tien and inhibitors or corrosion protection agents and the like. Be used.

According to the invention, preference is given to organic chemical binders least an alkyd resin or modified alkyd resin and / or a drying one vegetable oil contained in the medium or in the concentrate. According to the invention alkyd resins with an oil content of more than 45 wt .-%, preferably as 50 to 68 wt .-%, used.

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

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

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

Water is also particularly suitable as a solvent or diluent, optionally in a mixture with one or more of the above-mentioned orga nisch-chemical solvents or diluents, emulsifiers and dispersato ren.

A particularly effective wood protection is provided by industrial impregnation drive, e.g. B. vacuum, double vacuum or printing process.

The ready-to-use agents can optionally also be other insecticides and optionally contain one or more fungicides.

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

Very particularly preferred mixing partners can be insecticides, such as chloropyriphos, phoxime, silafluofin, alphamethrin, cyfluthrin, cypermethrin, delta methrin, permethrin, imidacloprid, NI-25, flufenoxuron, hexaflumuron and tri-flumuron,
as well as fungicides such as epoxyconazole, hexaconazole, azaconazole, propiconazole, tebuconazole, cyproconazole, metconazole, imazalil, dichlorofluoride, tolylfluanid, 3-iodo-2-propynylbutylcarbamate, N-octyl-isothiazolin-3-one and 4,5-dichloro - octylisothiazolin-3-one
The preparation and use of the active compounds according to the invention can be seen from the examples below.

Manufacturing examples example 1 (Method a)

To 2.9 g (0.0212 mol) of potassium carbonate and 2.0 g of 5-amino-1-t-butyl-3,4-dicyano pyrazole in 15 ml of dimethyl sulfoxide is a solution of 2.5 g (0.0106 mol) 1,3,5-trichloro-2,4,6-trifluorobenzene was added dropwise.

The reaction mixture is heated to 140 ° C. for 2 hours and then on ice water given. The resulting solid is filtered off and dried.

3.8 g (89% of theory) of N- (1-t-butyl-3,4-dicyano-pyrazol-5-yl) -2,4,6- trichloro-3,5-difluoro-aniline with a melting point of 175 ° C.  

Analogously to Example 1 or according to the general information on the preparation the compounds of formula (I) given in Table A below hold:

Table A

Examples of use

The following application examples list the following Compounds used as reference substances:

Example A Phaedon larval test

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

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

Cabbage leaves (Brassica oleracea) are dipped into the active ingredient preparation the desired concentration and treated with 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 1, 2 and 3 with an exemplary active ingredient concentration of 0.1% tion of more than 80% after 7 days, while that of the prior art known compound (A) caused no killing.  

Example B Plutella test

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

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

Cabbage leaves (Brassica oleracea) are dipped into the active ingredient preparation the desired concentration and treated with caterpillars (Plu tella maculipennis) 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 are removed were killed.

In this test, e.g. B. the compounds according to the preparation examples 1, 2 and 3 with an exemplary active ingredient concentration of 0.1% treatment of 100% after 7 days, while that known from the prior art Compound (A) did not kill.  

Example C Spodoptera Frugiperda test

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

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

Cabbage leaves (Brassica oleracea) are dipped into the active ingredient preparation the desired concentration and treated with caterpillars of the owl butterfly (Spo doptera frugiperda) occupied while the leaves are still moist.

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

In this test, e.g. B. the compounds according to the preparation examples 1 and 3 a killing at an exemplary active ingredient concentration of 0.001% treatment of 100% after 7 days, while that known from the prior art Compound (B) caused only 10% killing.  

Example D Nephotettix test

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

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

Rice seedlings (Oryza sativa) are dipped into the active ingredient preparation the desired concentration and treated with green rice leafhopper larvae (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 that no cicadas come off were killed.

In this test, e.g. B. the compounds according to the preparation examples 2 or 3, with an exemplary active ingredient concentration of 0.1%, killing of 100% or 95% after 6 days, while those from the prior art known compounds (A), (B), (C) and (D) did not cause killing.  

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

Solvent: 3 parts by weight of dimethylformamide
Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To prepare a suitable preparation of active compound, 1 Ge is mixed most of the active ingredient with the specified amount of solvent and the specified amount of emulsifier and dilute the concentrate with water containing emulsifier 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 immersion of 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 no spinning mites have been killed.

In this test, e.g. B. the compounds according to the preparation examples 1, 2 and 3 with an exemplary active ingredient concentration of 0.01% at least 90% after 13 days, while those from the state of the art nik known compound (A) caused no killing.

Claims (7)

1. Compounds of formula (I) in which
Ar stands for tetrasubstituted phenyl, whereby o-nitro is excluded as a substituent, or stands for pentasubstituted phenyl,
R¹ represents hydrogen or optionally substituted alkyl, alkenyl, alkynyl, aryl, aralkyl or hetaryl,
R² and R³ independently of one another represent hydrogen, halogen, cyano, nitro, in each case optionally substituted alkyl, aryl or hetaryl or one of the radicals CO₂R⁵, CONR⁶R⁷ or S (O) nR⁸ and
R⁴ for hydrogen each optionally substituted alkyl, alkenyl, alkynyl, aralkyl, aryloxy or aralkyloxy or for one of the radicals SO₂NR⁶R⁷, SO₂R⁹, COR¹⁰, CH₂N (R⁹) CO₂R⁵ or CH₂N (R⁹) SO₂R⁵
stands, where
R⁵ represents alkyl,
R⁶ and R⁷ independently of one another represent hydrogen or alkyl or together with the N atom to which they are attached form a ring which optionally contains one or more further heteroatoms,
R⁸ represents alkyl or haloalkyl,
R⁹ represents alkyl or optionally substituted aryl,
R¹⁰ represents alkyl, alkoxy or for optionally substituted aryl or aryloxy and
n stands for 0, 1 or 2. 2. A process for the preparation of compounds of formula (I) according to claim 1, characterized in that

• a) the compounds of the formula (I) are obtained if compounds of the formula (II) in which
  R¹, R² and R³ have the meaning given in claim 1, with compounds of the formula (III) Hal-Ar (III) in which
  Ar has the meaning given in claim 1 and
  Hal stands for halogen,
  in the presence of an acid acceptor and in the presence of a diluent
  and optionally the compounds of formula (Ia) thus obtained in which
  Ar, R¹, R² and R³ have the meaning given above,
  with compounds of the formula (IV) ER ^4-1 (IV) in which
  R ^{4-1 has} the meaning given in claim 1 for R⁴ with the exception of hydrogen and
  E represents an anionic leaving group,
  in the presence of an acid acceptor and optionally in the presence of a diluent; or
• b) compounds of the formula (Ib) in which
  Ar, R¹, R², R³ and R ^{4-1 have} the meaning given above, is obtained if compounds of the formula (II) in which
  R¹, R² and R³ have the meaning given above,
  with compounds of the formula (IV) ER ^4-1 (IV) in which
  E and R ^{4-1 have} the meaning given above,
  in the presence of an acid acceptor and in the presence of a diluent and the compounds of the formula (V) thus obtained in which
  R¹, R², R³ and R ^{4-1 have} the meaning given above, then with compounds of the formula (III) Hal-Ar (III) in which
  Ar and Hal have the meaning given above,
  in the presence of an acid acceptor and in the presence of a diluent.

3. pesticides, characterized by a content of minde at least one compound of formula (I) according to claim 1. 4. Use of compounds of formula (I) according to claim 1 for loading pest control. 5. A method for controlling pests, characterized in that compounds of formula (I) according to claim 1 to pests and / or let their living space take effect. 6. Process for the preparation of pesticides, thereby ge indicates that compounds of formula (I) according to claim 1 with Extenders and / or surfactants mixed. 7. Use of compounds of formula (I) according to claim 1 for the preparation provision of pesticides.