DE4303658A1 - Substituted tetrahydropyridazinecarboxamides - Google Patents

Description

The invention relates to novel substituted Tetrahydropyridazincarboxamide, a Verfah for their production and their use as pesticides.

Certain tetrahydropyridazinecarboxamides, such as 3- (4-fluorophenyl) - 5,6-dihydro-N- [4- (trifluoromethyl) phenyl] -1 (4H) -pyridazinecarboxamide are already have become known (see WO 9117983) and show good activity against animal pests.

The level of action or duration of action of these known compounds is however, especially for certain organisms or for low users concentrations are not completely satisfactory in all areas of application.

There have been new substituted Tetrahydropyridazincarboxamide the general Formula (I)

found in which
R ^{1 is} hydrogen or alkyl,
R ^{2 is} alkylcarbonyl or alkoxycarbonyl or
R ¹ and R ² together with the nitrogen atom to which they are attached form an optionally substituted heterocycle,
X is halogen, haloalkyl, haloalkoxy or haloalkylthio,
Y is halogen, haloalkyl, haloalkoxy or haloalkylthio,
m is the number 0, 1, 2 or 3 and
n stands for the number 0, 1, 2 or 3.

Furthermore, it was found that the new Tetrahydropyridazincarboxamide the general formula (I)

in which
R ^{1 is} hydrogen or alkyl,
R ^{2 is} alkylcarbonyl or alkoxycarbonyl or
R ¹ and R ² together with the nitrogen atom to which they are attached form an optionally substituted heterocycle,
X is halogen, haloalkyl, haloalkoxy or haloalkylthio,
Y is halogen, haloalkyl, haloalkoxy or haloalkylthio,
m is the number 0, 1, 2 or 3 and
n is the number 0, 1, 2 or 3,
if
Butyrophenone hydrazones of the general formula (II)

in which
R ¹ , R ² , X and n have the meanings given above,
with isocyanates of the formula (III)

in which
Y and m have the meanings given above,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid acceptor,
R ^{1 is} hydrogen or alkyl,
R ^{2 is} alkylcarbonyl or alkoxycarbonyl or
R ¹ and R ² together with the nitrogen atom to which they are attached form an optionally substituted heterocycle,
X is halogen, haloalkyl, haloalkoxy or haloalkylthio,
n stands for the number 0, 1, 2 or 3.

The invention also provides butyrophenone hydrazones of the general formula (II)

in which
R ^{1 is} hydrogen or alkyl,
R ^{2 is} alkylcarbonyl or alkoxycarbonyl or
R ¹ and R ² together with the nitrogen atom to which they are attached form an optionally substituted heterocycle,
X is halogen, haloalkyl, haloalkoxy or haloalkylthio,
n stands for the number 0, 1, 2 or 3.

The compounds of formula (II) can be prepared by adding ω-chloro ketones of the formula (IV)

in which
R ¹ , R ² , X and n have the meanings given above,
optionally reacted with hydrazine hydrate in the presence of a diluent at temperatures between 0 ° C and 50 ° C.

Surprisingly, it has been found that the new substituted tetrahydropyride azincarboxamide of the general formula (I) distinguished by excellent insecticides Distinguish effects.

Preference is given to substituted tetrahydropyridazinecarboxamides of the formula (I) in which
R ^{1 is} hydrogen or C ₁ -C ₄ -alkyl,
R ^{2 is} alkyl-C ₁ -C ₄ -carbonyl or alkoxy-C ₁ -C ₄ -carbonyl or
R ¹ and R ^2, together with the nitrogen atom to which they are attached, represent an optionally 5- or 6-membered saturated or unsaturated and optionally substituted by halogen, alkyl, alkoxy, haloalkyl, haloalkoxy, haloalkylthio, hydroxy, nitro or cyano heterocyclic ring which optionally contains further heteroatoms from the series oxygen, sulfur or nitrogen and which is optionally interrupted by a carboxyl group,
X is halogen, C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ -haloalkoxy, C ₁ -C ₄ -halogenoalkylthio,
Y is halogen, C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ -haloalkoxy, C ₁ -C ₄ -halogenoalkylthio,
m is the number 0, 1, 2 or 3 and
n stands for the number 0, 1, 2 or 3.

Particularly preferred are substituted Tetrahydropyridazincarboxamide of formula (I), in which
R ^{1 is} hydrogen, methyl, ethyl, n-propyl and i-propyl,
R ^{2 is} methylcarbonyl, methoxycarbonyl or ethoxycarbonyl or
R ¹ and R ² together with the nitrogen atom to which they are attached form an optionally 5- or 6-membered saturated or unsaturated, optionally substituted by fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl, trifluoromethoxy or trifluoromethylthio, substituted heterocyclic ring which optionally contains 1 or 2 further heteroatoms from the series oxygen or nitrogen and which is optionally interrupted by a carbonyl group,
X is fluorine, chlorine, bromine, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, difluoromethyl or difluoromethoxy,
Y is fluorine, chlorine, bromine, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, difluoromethyl or difluoromethoxy,
m stands for the number 1 or 2 and
n stands for the number 0, 1 or 2.

Specifically, except the compounds mentioned in the preparation examples the following substituted Tetrahydropyridazincarboxamide the general formula (I) called:

Table 1

For example, using 2- (4-chloropyrazolyl) 4-chloro-4'-fluorobutyrophenone hydrochloride drazon and 4-trifluoromethylphenyl isocyanate as starting materials, the reac tion sequence of the process according to the invention by the following reaction scheme be reproduced:

The butyrophenone hydrazones to be used as starting materials in the process according to the invention for the preparation of the compounds of the formula (I) are generally defined by the formula (II). In formula (II), R ¹ , R ² , X and n preferably or in particular have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) preferably or particularly preferably for R ¹ , R ² , X and n were specified.

The compounds of formula (II) are novel and subject of the invention. you can be prepared in an analogous manner by methods known per se, by reacting ω-chloroketones of the formula (IV)

in which
R ¹ , R ² , X and n have the meanings given above,
optionally reacted with hydrazine hydrate in the presence of a diluent, such as ethanol, at temperatures between 0 ° C and 50 ° C (see Preparation Example).

In the following, apart from the compounds mentioned in the preparation examples the following compounds of the formula (II) are mentioned:

Table 2

The compounds of the formula (IV) to be used as starting materials for the preparation of the compounds of the formula (II) are generally defined by the formula (IV). In formula (IV), R ¹ , R ² , X and n preferably or in particular have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) preferably or particularly preferably for R ¹ , R ² , X and n were specified.

The compounds of formula (IV) are partially new. You can look after yourself known methods are prepared in an analogous manner by using compounds of the formula (V)

in which
X and n have the meanings given above,
with compounds of the formula (VI)

in which
R ¹ and R ^{2 have} the meanings given above,
optionally in the presence of an inert diluent, preferably nitriles such as acetonitrile, ketones such as acetone or amides such as dimethylformamide and optionally in the presence of bases such as alkaline earth carbonates, tert. Alcoholates, alkali hydrides or tert. Amines at temperatures from -20 ° C to 40 ° C, preferably at -10 ° C to 10 ° C in a molar ratio with each other under atmospheric pressure (see Preparation Example, EP-237916, EP-237917 and US 3,951,978).

In the following, apart from the compounds mentioned in the preparation examples the following compounds of the formula (IV) are mentioned:

Table 3

The compounds of the formulas (V) are known or can be known Methods are obtained (see, for example, EP-237916 and EP-237917).

The compounds of the formula (VI) and those required as starting compounds Isocyanates of the formula (III) are generally known compounds of the organic Chemistry.  

The active compounds are suitable for controlling animal pests, preferably arthropods and nematodes, in particular insects and arachnids, which occur in agriculture, in forests, in the protection of stored products and materials, and in the hygiene sector. They are effective against normally sensitive and resistant species as well as against all or individual stages of development. The above mentioned pests include:
From the order of Isopoda z. Oniscus asellus, Armadillidium vulgare, Porcellio scaber.

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

From the order of Chilopoda z. Geophilus carpophagus, Scutigera spec.

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

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

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

From the order of Isoptera z. Reticulitermes spp.

From the order of Anoplura z. Phylloxera vastatrix, Pemphigus spp., Pediculus humanus corporis, Haematopinus spp., Linognathus spp.

From the order of Mallophaga z. B. Trichodectes spp., Damalinea spp.

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

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

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

From the order of Coleoptera z. B. Anobium punctatum, Rhizopertha dominica, Acanthoscelides obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachna varive stis, Atomaria spp., Oryzaephilus surinamensis, Antho nomus 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. Cono derus spp., Melolontha melolontha, Amphimallon solsti tialis, Costelytra zealandica.

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

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

From the order of Arachnida z. B. Scorpio maurus, Latrodectus mactans.

From the order of Acarina z. 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 active compounds according to the invention are distinguished by a high insecticidal and acaricidal activity.

They can be combated with particularly good success phytopathogenic insects, such as the larvae of the Horseradish leaf beetle (Phaedon cochleariae) or against the caterpillars of the cabbage (Plutella maculipennis).

The active compounds according to the invention can also be used with particularly good results Combating parasitic warm-blooded pests, such as against the larvae of the gold fly (Lucilia cuprina) insert.

The active compounds can be converted into the customary formulations, such as Solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, solvents Liche powders, granules, suspension-emulsion concentrates, drug-impregnated Natural and synthetic substances as well as finest encapsulation in polymeric substances.

These formulations are prepared in a known manner, for. B. by mixing the active ingredients with extenders, ie liquid solvents and / or solid  Carriers, optionally with the use of surfactants, ie Emulsifiers and / or dispersants and / or foam-forming agents.

In the case of using water as an extender z. B. also organic Solvent can be used as auxiliary solvent. As liquid solvents are essentially in question: aromatics, such as xylene, toluene, or Alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic Hydrocarbons, such as cyclohexane or paraffins, for. B. petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol and theirs Ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or Cyclohexanone, strongly polar solvents, such as dimethylformamide and Dimethyl sulfoxide, as well as water.

Suitable solid carriers are:
z. As ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic stone powders, such as finely divided silica, alumina and silicates, as solid carriers for granules are: z. B. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic flours and granules of organic material such as sawdust, coconut shells, corncobs and Ta bakstengeln; as emulsifying and / or foam-producing agents are in question: z. Nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. B. alkylaryl polyglycol ether, alkyl sulfonates, alkyl sulfates, arylsulfonates and protein hydrolysates; as dispersants come into question; z. As lignin-sulphite liquors and methylcellulose.

It can in the formulations adhesives such as carboxymethylcellulose, natural and synthetic powdery, granular or latex-shaped polymers are used, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, as well as natural Phospholipids such as cephalins and lecithins and synthetic phospholipids. Further Additives can be mineral and vegetable oils.  

It can dyes such as inorganic pigments, eg. For example, iron oxide, titanium oxide, Ferrocyan blue and organic dyes such as alizarin, azo and Metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, Boron, copper, cobalt, molybdenum and zinc are used.

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

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

Also a mixture with other known active ingredients, such as fungicides, Insecticides, acaricides, nematicides, bird repellents, Plant nutrients and soil conditioners are possible.

The active compounds can be used as such, in the form of their formulations or the resulting prepared by further dilution, such as ready-to-use Solutions, suspensions, emulsions, powders, pastes and granules applied become. The application is done in the usual way, for. B. by pouring, spraying, Spraying, sprinkling.

The active compounds according to the invention can be used both before and after emergence the plants are applied.

They can also be incorporated into the soil before sowing.

The amount of active ingredient used can vary within a substantial range. you depends essentially on the nature of the desired effect. In general the application rates are between 0.01 and 10 kg of active ingredient per hectare Soil area, preferably between 0.05 and 5 kg per ha.

The preparation and use of the active compounds according to the invention is based on following examples.

Preparation Examples Example (I-1)

A mixture of 2.36 g (7.5 mmol) of 2- (4-chloropyrazolyl) -4-chloro-4'-fluorobutyro phenonhydrazone, 1.4 g (7.5 mmol) of 4-trifluoromethylphenyl isocyanate and 20 ml Acetonitrile is stirred overnight at room temperature. Then you distill this Solvent in vacuo and the residue is triturated with ethanol. The product is filtered off with suction and washed with ethanol and hexane.

This gives 1.4 g (40% of theory) of 1- (4-trifluoromethylphenylamino) carbonyl-3- (4- fluorophenyl) -4- (4-chloropyrazolyl) -3,4,6,1-tetrahydropyridazine as a colorless powder with the melting point 215-216.5 ° C.  

The following compounds of the formula (I) are obtained in an analogous manner:

Table 4

Preparation of the starting compounds (Example (II-1)

A solution of 3 g (0.01 mol) of 2- (4-chloropyrazolyl) -4-chloro-4'-fluorobutyrophenone in 20 ml of ethanol are added 1.2 g (0.02 mol) of hydrazine hydrate. You leave the mixture stand overnight at room temperature and then distilled the solvent in Vacuum off. The residue is mixed with 30 ml of hexane, after addition of 1-2 ml Ethanol, the product is crystalline and can be filtered with suction.

This gives 1.5 g (48% of theory) of 2- (4-chloropyrazolyl) -4-chloro-4'-fluorobutyro phenonhydrazone as a beige powder with the melting point 121-125 ° C.  

The following compounds of the formula (II) are obtained in an analogous manner.

Table 5

Production of precursors Example (IV-1)

To a mixture of 2.8 g (0.02 mol) of 4-chloropyrazole hydrochloride, 5.6 g (0.0405 Mol) potassium carbonate and 50 ml of acetonitrile are added slowly at 5-10 ° C 5.6 g (0.02 Mol) 2-bromo-4-chloro-4'-fluorobutyrophenone and then stirred overnight Room temperature after. Then it is filtered off from the salt, washed with acetonitrile and then the filtrate evaporated in vacuo. The residue is triturated with hexane and sucks after crystallization.

This gives 4.3 g (71% of theory) of 2- (4-chloropyrazolyl) -4-chloro-4'- Fluorobutyrophenone in the form of yellow crystals with the melting point 98.5-100 ° C (from Hexane / EtOH 100: 1).  

In an analogous manner, the following compounds of formula (IV)

getting produced:

Table 6

Preparation of the starting materials Example (V-1)

To a solution of 44 g (0.22 mol) of 4-chloro-4'-fluorobutyrophenone in 150 ml of chloroform is added dropwise 35.2 g (0.22 mol) of bromine. The mixture is stirred until decolorization at room temperature, then blows out the hydrogen bromide with CO ₂ and the solvent is distilled off in vacuo.

This gives 62 g (quant.) Of 2-bromo-4-chloro-4'-fluorobutyrophenone in the form of a light brown oil with the refractive index n ²⁰ _D = 1.5651.

applications

In the following application examples, the following was Compound used as a comparison substance

3- (4-Fluorophenyl) -5,6-dihydro-N- [4- (trifluoromethyl) phenyl] -1 (4H) -pyr-idazine carboxamide
(known from WO 9117983).

Example A Phaedon larvae 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 Part by weight of active compound with the stated amount of solvent and the given amount of emulsifier and the concentrate is diluted with water to the ge wanted concentration.

Cabbage leaves (Brassica oleracea) are dipped in the preparation of active ingredient treated with the desired concentration and with horseradish leaf beetle larvae (Phaedon cochleariae) as long as the leaves are still moist.

After the desired time, the plants with horseradish leaf beetle larvae (Phaedon cochleariae) occupied. After every 3 days, the kill in% certainly. 100% means that all beetle larvae have been killed; 0% means that no beetle larvae were killed.

In this test, z. B. the following compounds of the preparation examples superior efficiency over the prior art: (I-1), (I-2), (I-4), (I-5), (I-7), (I-8), (I-10), (I-12) and (I-13).  

Example B Plutella Test

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

To prepare a suitable preparation of active compound, 1 Part by weight of active compound with the stated amount of solvent and the given amount of emulsifier and the concentrate is diluted with water to the ge wanted concentration.

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

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

In this test, z. B. the following compounds of the preparation examples superior efficiency over the prior art: (I-I), (I-2), (I-3), (I-4), (I-8), (I-10), (I-12) and (I-13).  

Example C Blowfly larvae test

Test animals: Lucilia cuprina larvae emulsifier: 35 parts by weight of ethylene glycol monomethyl ether 35 parts by weight of nonylphenol polyglycol ether

To prepare a suitable preparation of active compound, three are mixed Parts by weight of active ingredient with seven parts by weight of the mixture indicated above and dilute the emulsion concentrate thus obtained with water to each desired concentration.

Approximately 20 Lucilia cuprina res.-larvae are placed in a test tube containing about 1 cm ³ horse meat and 0.5 ml of the active ingredient preparation. After 24 hours, the effectiveness of the preparation of the active ingredient is determined. 100% means that all Blowfly larvae have been killed; 0% means that no Blowfly larvae were killed.

In this test, z. B. the following compounds of the preparation examples a superior effect over the prior art: (I-I), (I-2) and (I-9).

Claims (10)

1. Substituted tetrahydropyridazinecarboxamides of the general formula (I) in which
R ^{1 is} hydrogen or alkyl,
R ^{2 is} alkylcarbonyl or alkoxycarbonyl or
R ¹ and R ² together with the nitrogen atom to which they are attached form an optionally substituted heterocycle,
X is halogen, haloalkyl, haloalkoxy or haloalkylthio,
Y is halogen, haloalkyl, haloalkoxy or haloalkylthio,
m is the number 0, 1, 2 or 3 and
n stands for the number 0, 1, 2 or 3. 2. Process for the preparation of substituted tetrahydropyridazinecarboxamides of the general formula (I) in which
R ^{1 is} hydrogen or alkyl,
R ^{2 is} alkylcarbonyl or alkoxycarbonyl or
R ¹ and R ² together with the nitrogen atom to which they are attached form an optionally substituted heterocycle,
X is halogen, haloalkyl, haloalkoxy or haloalkylthio,
Y is halogen, haloalkyl, haloalkoxy or haloalkylthio,
m is the number 0, 1, 2 or 3 and
n is the number 0, 1, 2 or 3,
characterized in that
Butyrophenone hydrazones of the general formula (II) in which
R ¹ , R ² , X and n have the meanings given above,
with isocyanates of the formula (III) in which
Y and m have the meanings given above,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid acceptor,
R ^{1 is} hydrogen or alkyl,
R ^{2 is} alkylcarbonyl or alkoxycarbonyl or
R ¹ and R ² together with the nitrogen atom to which they are attached form an optionally substituted heterocycle,
X is halogen, haloalkyl, haloalkoxy or haloalkylthio,
n stands for the number 0, 1, 2 or 3. 3. Butyrophenone hydrazones of the general formula (II) in which
R ^{1 is} hydrogen or alkyl,
R ^{2 is} alkylcarbonyl or alkoxycarbonyl or
R ¹ and R ² together with the nitrogen atom to which they are attached form an optionally substituted heterocycle,
X is halogen, haloalkyl, haloalkoxy or haloalkylthio,
n stands for the number 0, 1, 2 or 3. 4. A process for preparing the compounds of the formula (II) according to claim 3, characterized in that ω-chloroketones of the formula (IV) in which
R ¹ , R ² , X and n have the meanings given in claim 3,
optionally reacted with hydrazine hydrate in the presence of a diluent at temperatures between 0 ° C and 50 ° C. 5. Substituted Tetrahydropyridazincarboxamide of formula (I) according to claim 1, wherein
R ^{1 is} hydrogen or C ₁ -C ₄ -alkyl,
R ^{2 is} alkyl-C ₁ -C ₄ -carbonyl or alkoxy-C ₁ -C ₄ -carbonyl or
R ¹ and R ^2, together with the nitrogen atom to which they are attached, represent an optionally 5- or 6-membered saturated or unsaturated and optionally substituted by halogen, alkyl, alkoxy, haloalkyl, haloalkoxy, haloalkylthio, hydroxy, nitro or cyano heterocyclic ring which optionally contains further heteroatoms from the series oxygen, sulfur or nitrogen and which is optionally interrupted by a carboxyl group,
X is halogen, C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ -haloalkoxy, C ₁ -C ₄ -haloalkylthio,
Y is halogen, C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ -haloalkoxy, C ₁ -C ₄ -haloalkylthio,
m is the number 0, 1, 2 or 3 and
n stands for the number 0, 1, 2 or 3. 6. Substituted Tetrahydropyridazincarboxamide of formula (I) according to claim 1, wherein
R ^{1 is} hydrogen, methyl, ethyl, n-propyl and i-propyl,
R ^{2 is} methylcarbonyl, methoxycarbonyl or ethoxycarbonyl or
R ¹ and R ² together with the nitrogen atom to which they are attached, an optionally 5- or 6-membered saturated or unsaturated, optionally substituted by fluorine, chlorine, bromine, methyl, methoxy, trifluoro methyl, trifluoromethoxy or trifluoromethylthio, substituted heterocyclic Ring, which optionally contains 1 or 2 further heteroatoms from the series oxygen or nitrogen and which is optionally interrupted by a carbonyl group,
X is fluorine, chlorine, bromine, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, difluoromethyl or difluoromethoxy,
Y is fluorine, chlorine, bromine, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, difluoromethyl or difluoromethoxy,
m stands for the number 1 or 2 and
n stands for the number 0, 1 or 2. 7. pesticides, characterized by a content of min at least one substituted tetrahydropyridazinecarboxamide of the formula (I) according to claim 1.   8. Use of substituted Tetrahydropyridazincarboxamiden of the formula (I) according to claim 1 for controlling pests. 9. A method for controlling pests, characterized in that Substituted tetrahydropyridazinecarboxamides of the formula (I) according to Claim 1 to act on pests and / or their habitat. 10. A process for the preparation of pesticides, characterized characterized in that substituted tetrahydropyridazinecarboxamides of Formula (I) according to claim 1 with extenders and / or surface-active Mixtures mixed.