Substituted isothioureas.

0001The present invention relates to new, substituted N-pyridylmethyl-N'-cyano-isothioureas, processes for their preparation and their use in pest control and as starting products for the synthesis of new pesticides.

0002The invention relates to new compounds of formula 1<chemistry id="chem0001" num="0001"><img file="EP0303570A2_D0001.tif" /></chemistry>wherein<ul id="ul0001" list-style="none"><li>RC_l-C₄-Alkyl or benzyl;</li><li>R₁ C._l-C₄-Alkyl;</li><li>X halogen; and</li><li>n is a number 0, 1, 2 or 3</li><li>mean.</li></ul>

0003According to the invention, preference is given to compounds of the formula I in which<ul id="ul0002" list-style="none"><li>R is methyl, ethyl or benzyl;</li><li>R₁ Methyl;</li><li>X chlorine; and</li><li>n is a number 0, 1 or 2</li><li>mean.</li></ul>

0004According to the invention, preference is furthermore given to compounds of the formula I in which<ul id="ul0003" list-style="none"><li>R and R₁ Methyl; and</li><li>n is the number 0</li><li>mean.</li></ul>

0005Of particular interest are those compounds of formula I according to the invention in which the pyridyl radical is a pyrid-3-yl or pyrid-4-yl radical.

0006The term alkyl itself or as a constituent of another substituent is to be understood as meaning straight-chain or branched and, depending on the number of carbon atoms specified in the context of the present invention, for example the following groups: methyl, ethyl, propyl, butyl, and their isomers, such as isopropyl, isobutyl, tert-butyl, sec-butyl.

0007The term halogen in the context of the present invention is to be understood as fluorine, chlorine and bromine, preferably fluorine and chlorine.

0008The present subject matter of the invention also includes the salts, in particular the plant physiologically acceptable salts, of the compounds of the formula I. Such salts with organic and inorganic acids are, for example the following into consideration: chlorides, bromides, iodides, sulfates, hydrogen sulfates, chlorates, perchlorates, rhodanides, nitrates, phosphates, hydrogen phosphates, tetrafluoroborates, formates, acetates, trichloroacetates, trifluoroacetates, phenylsulfonates, oxalates, malonates, citrates, succinates, succinates .

0009The compounds of the formula I can be prepared in a manner known per se (cf., for example, JP patent application Kokai No. 62-234064; JB Hendrickson et al, "Organic Chemistry", McGraw Hill Book Co., 1970, pp. 378-382) by using a compound of formula II<chemistry id="chem0002" num="0002"><img file="EP0303570A2_D0002.tif" /></chemistry>with a compound of formula III<chemistry id="chem0003" num="0003"><img file="EP0303570A2_D0003.tif" /></chemistry>implements; where in formulas II and III R, R₁, X and n have the meanings given above. In this reaction, one of the radicals -SR is a leaving group which can be split off under the reaction conditions.

0010The above process variants leading to the compounds of the formula according to the invention are preferably carried out in a solvent. Suitable solvents are, for example aromatic hydrocarbons such as benzene, toluene and xylene; Ketones such as acetone, cyclohexanone and methyl ethyl ketone; Ethers such as tetrahydrofuran, dioxane and diethyl ether; halogenated hydrocarbons such as chloroform, carbon tetrachloride and chlorobenzene; Alcohols such as ethanol and propanol; Esters of aliphatic acids, such as ethyl acetate; aliphatic amides such as dimethylformamide and dimethylacetamide; Dimethyl sulfoxide, acetonitrile and other solvents that do not affect the reaction. These solvents can also be used as mixtures. The reaction temperature can be in a wide range from -10 to + 150 ° C. A temperature range of approximately 20 ° to 80 ° C. is preferred.

0011The starting compounds of the formulas II and III are known or, if they are new, they can be obtained analogously to known methods. For example, the N-cyanothioiminocarbonates of the formula 11 and their preparation from Chem. Ber. 100: 2604-15 (1967); J. Straight. Chem. 19, 1205-6 (1982) and JP patent application SHO 61-76044. The picolylamine compounds of the formula III are also known or they can be, for example, analogous to Tetrahedron Letters Vol. 26, 5863 (1985) or Agr. Biol. Chem. 32, 747 (1968).

0012N-picolyl-N'-cyano-isothioureas, their preparation and their use as pharmaceuticals have already been described in JP patent application SHO 61-76044. In contrast, the compounds of the formula I according to the invention differ structurally by the alkyl substitution on the N atom (R.₁ in formula I).

0013It has now surprisingly been found that the guanidine compounds of the formula I according to the invention have excellent activity as pesticides with good plant tolerance and low toxicity to warm-blooded animals. They are particularly suitable for controlling plants and animals infesting pests.

0014The compounds of the formula I are particularly suitable for controlling insects of the orders Lepidoptera, Coleoptera, Homoptera, Heteroptera, Diptera, Thysanoptera, Orthoptera, Anoplura, Siphonaptera, Mallophaga, Thysanura, Isoptera, Psocoptera and Hymenoptera and representatives of the order Akarina. The good pesticidal activity of the compounds according to the invention corresponds to a mortality rate of at least 50-60% of the pests mentioned.

0015With the aid of the compounds of the formula according to the invention, above all plant-damaging insects, especially plant-damaging insects in ornamental and useful plants, in particular in cotton crops, vegetable crops, rice crops and fruit crops, can be combated. In this context, it should be emphasized that the compounds mentioned are characterized both by a strong systemic action, but above all by a contact action against sucking insects, in particular against insects of the Aphididae family (such as, for example, Aphis fabae, Aphis craccivora and Myzus persicae) difficult to fight with conventional means, award.

0016The compounds of the formula are furthermore distinguished by a good action against larval insect stages and nymphs, especially from eating insect pests. In particular, the compounds of the formula I can be used with excellent success against plant-damaging cicadas, especially in rice crops. In this connection, attention is drawn to the low fish toxicity of the compounds according to the invention.

0017The compounds are also suitable for controlling ectoparasites, for example Lucilia sericata, and ticks on domestic and farm animals, for example by treating animals, stables and pastures.

0018The action of the compounds according to the invention or of the compositions comprising them can be broadened considerably by adding other insecticides and / or acaricides and adapted to the given circumstances. Representatives of the following classes of active substances are suitable as additives: organic phosphorus compounds, nitrophenols and derivatives, formamidines, ureas, carbamates, pyrethroids, chlorinated, hydrocarbons and Bacillus thuringiensis preparations.

0019The compounds of formula 1 are used in unchanged form or preferably together with the auxiliaries customary in formulation technology and are therefore used, for example, to form emulsion concentrates, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granules, and also encapsulations in, for example, polymers Fabric processed in a known manner. The application methods, such as spraying, atomizing, dusting, scattering or pouring, as well as the means are chosen in accordance with the intended goals and the given conditions.

0020The formulation, ie the agent, or combinations of these agents with other insecticides or acaricides, and, if appropriate, compositions, preparations or compositions comprising a solid or liquid additive are prepared in a known manner, for example by intimately mixing and / or grinding the agents with Extenders, such as with solvents, solid carriers, and optionally surface-active compounds (surfactants).

0021Possible solvents are: aromatic hydrocarbons, preferably fractions C₈ to C₁₂, such as Xylene mixtures or substituted naphthalenes, phthalic esters, such as dibutyl or dioctyl phthalate, aliphatic hydrocarbons, such as cyclohexane, paraffins, alcohols and glycols, and their ethers and esters, such as ethanol, ethylene glycol, ethylene glycol monomethyl or ethyl ether, ketones, such as cyclohexane, such as cyclohexane , such as N-methyl-2-pyrrolidone, dimethyl sulfoxide or dimethylformamide, and optionally epoxidized vegetable oils, such as epoxidized coconut oil or soybean oil, or water. Natural rock flours, such as calcite, talc, kaolin, montmorillonite or attapulgite, are generally used as solid carriers, for example for dusts and dispersible powders. To improve the physical properties, highly disperse silicas or highly disperse absorbent polymers can also be added. Porous types such as, for example, come as granular, adsorptive granule carriers Pumice stone, broken brick, sepiolite or bentonite, as non-sorptive carrier materials, for example calcite or sand. In addition, a large number of granulated materials of inorganic or organic nature, such as in particular dolomite or comminuted plant residues, can be used.

0022Depending on the nature of the active ingredient of the formula I to be formulated or the combinations of these active ingredients with other insecticides or acaricides, non-ionic, cationic and / or anionic surfactants with good emulsifying, dispersing and wetting properties are suitable as surface-active compounds. Surfactants are also to be understood as mixtures of surfactants.

0023Suitable anionic surfactants can be both so-called water-soluble soaps and water-soluble synthetic surface-active compounds.

0024Suitable soaps are the alkali, alkaline earth or optionally substituted ammonium salts of higher fatty acids (C ↑ α-C₂₂), such as the Na or K salts of oleic or stearic acid, or of natural fatty acid mixtures which can be obtained, for example, from coconut or tall oil. Also to be mentioned as surfactants are the fatty acid methyl taurine salts and modified and unmodified phospholipids. However, so-called synthetic surfactants are used more frequently, in particular fatty sulfonates, fatty sulfates, sulfonated benzimidazole derivatives or alkylarylsulfonates.

0025The fatty sulfonates or sulfates are generally present as alkali, alkaline earth or optionally substituted ammonium salts and generally have an alkyl radical with 8 to 22 carbon atoms, alkyl also including the alkyl part of acyl radicals, for example the Na or Ca Salt of lignin sulfonic acid, dodecylsulfuric acid ester or a fatty alcohol sulfate mixture made from natural fatty acids. This subheading also includes the salts of sulfuric acid esters and sulfonic acids from fatty alcohol-ethylene oxide adducts. The sulfonated benzimidazole derivatives preferably contain 2 sulfonic acid groups and a fatty acid residue with about 8-22 carbon atoms. Alkylarylsulfonates are, for example, the sodium, calcium or triethanolamine salts of dodecylbenzenesulfonic acid, dibutylnaphthalenesulfonic acid or a naphthalenesulfonic acid / formaldehyde condensation product. Corresponding phosphates, such as, for example, also come Salts of the phosphoric acid ester of a p-nonylphenol (4-14) ethylene oxide adduct, in question.

0026Suitable nonionic surfactants are primarily polyglycol ether derivatives of aliphatic or cycloaliphatic alcohols, saturated or unsaturated fatty acids and alkylphenols, which can contain 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 the alkylphenols. Other suitable nonionic surfactants are the water-soluble 20 to 250 ethylene glycol ether groups and 10 to 100 propylene glycol ether groups containing polyethylene oxide adducts with polypropylene glycol, ethylene diaminopolypropylene glycol and alkyl polypropylene glycol with 1 to 10 carbon atoms in the alkyl chain. The compounds mentioned usually contain 1 to 5 ethylene glycol units per propylene glycol unit.

0027Examples of nonionic surfactants are nonylphenol polyethoxyethanols, castor oil polyglycol ethers, polypropylene-polyethylene oxide adducts, tributylphenoxypolyethoxyethanol, polyethylene glycol and octylphenoxy polyethoxyethanol. Fatty acid esters of polyoxyethylene sorbitan, such as polyoxyethylene sorbitan trioleate, are also suitable.

0028The cationic surfactants are primarily quaternary ammonium salts which contain at least one alkyl radical having 8 to 22 carbon atoms as N substituents and have lower, optionally halogenated alkyl, benzyl or lower hydroxyalkyl radicals as further substituents. These salts are preferably in the form of halides, methyl sulfates or ethyl sulfates, for example the stearyl trimethyl ammonium chloride or the benzyl di (2-chloroethyl) ethyl ammonium bromide.

0029The surfactants commonly used in formulation technology are described, inter alia, in the following publications: "Mc Cutcheon's Detergents and Emulsifiers Annual" MC Publishing Corp., Ridgewood, New Jersey, 1979; Dr. Helmut Stache "Tensid Taschenbuch", Carl Hanser Verlag Munich / Vienna 1981.

0030The pesticidal preparations generally contain, based on the weight, 0.1 to 99%, in particular 0.1 to 95% ^Ofo, an active ingredient of the formula I or combinations thereof with other insecticides or acaricides, 1 to 99.9% of a solid or liquid additive and 0 to 25%, in particular 0.1 to 20 ^O/ o, a surfactant. While concentrated agents are preferred as a commercial product, the end user generally uses diluted preparations which have substantially lower active substance concentrations, for example 0.1 to 1000 ppm.

0031The agents can also contain other additives such as stabilizers, defoamers, viscosity regulators, binders, adhesives and fertilizers or other active ingredients to achieve special effects.

0032The isothiourea compounds of the formula I according to the invention are also suitable for using the starting materials or intermediates for the preparation of pesticidal, in particular insecticidal, effective guanidine compounds. The present invention therefore furthermore relates to the use of a compound of the formula I for the preparation of pesticidally active guanidine compounds of the formula IV and their tautomers<chemistry id="chem0004" num="0004"><img file="EP0303570A2_D0004.tif" /></chemistry>wherein<ul id="ul0004" list-style="none"><li>R₁ and R₂ independently of each other C₁-C₄-Alkyl,</li><li>Rs hydrogen, C₁-Ca-alkyl, benzyl or picolyl; or</li><li>R₂ and Rs together a remainder (̵CH₂)̵₄ or (̵CH₂)̵₅;</li><li>X halogen; and</li><li>n is a number 0, 1, 2 or 3;</li></ul>mean by reacting a compound of formula I with a compound of formula V.<chemistry id="chem0005" num="0005"><img file="EP0303570A2_D0005.tif" /></chemistry>where R₂ and R₃ have the meanings given above.

Example 1: Preparation of N-pyrid-3-ylmethyl-N-methyl-N'-cyano-S-methylisothio-urea

00335.1 g of dimethyl-N-cyanothioiminocarbonate, 4.3 g of 3-methylaminomethylpyridine and 10.6 g of ammonium acetate in 20 ml of ethanol are kept under reflux for 8 hours. After the reaction mixture has cooled, the salts are removed and the solvents are distilled. After purification by chromatography, the product is isolated as a light oil. In this way the title compound of the formula<chemistry id="chem0006" num="0006"><img file="EP0303570A2_D0006.tif" /></chemistry>with a refraction of <maths id="math0001" num=""><img file="EP0303570A2_D0007.tif" /></maths>= 1.6098 (Compound No. 1) obtained.

0034As listed above, the following compounds of formula I are also prepared:<tables id="tabl0001" num="0001"><img file="EP0303570A2_D0008.tif" /></tables>

As indicated above, the following compounds of formula I are also available:

0035<tables id="tabl0002" num="0002"><img file="EP0303570A2_D0009.tif" /></tables>

Example 2: Preparation of N-pyrid-3-ylmethyl-N-methyl-N'-cyano-N "-n-butylguanidine

00364.5 g of the compound No. 1 prepared according to Example 1 are kept under reflux for 16 hours together with 2 ml of n-butylamine and 20 ml of ethanol. After the volatile components have been distilled off on a rotary evaporator, the residue is purified by chromatography on a silica gel column, eluting with dichloromethane / methanol (90/10% by volume). The title compound of the formula is obtained<chemistry id="chem0007" num="0007"><img file="EP0303570A2_D0010.tif" /></chemistry>as a light yellow oil (<maths id="math0002" num=""><img file="EP0303570A2_D0011.tif" /></maths>=1,5598).

Example 3: Formulations for liquid active compounds of the formula according to Example 1 or combinations of these active compounds with other insecticides or acaricides (% = weight percent):

0037<tables id="tabl0003" num="0003"><img file="EP0303570A2_D0012.tif" /></tables>

0038Emulsions of any desired concentration can be prepared from such concentrates by dilution with water.<tables id="tabl0004" num="0004"><img file="EP0303570A2_D0013.tif" /></tables>

0039The solutions are suitable for use in the form of tiny drops.<tables id="tabl0005" num="0005"><img file="EP0303570A2_D0014.tif" /></tables>

0040The active ingredient is dissolved in methylene chloride, sprayed onto the carrier and the solvent is then evaporated off in vacuo.<tables id="tabl0006" num="0006"><img file="EP0303570A2_D0015.tif" /></tables>

0041Ready-to-use dusts are obtained by intimately mixing the carrier substances with the active ingredient.

Formulations for solid active compounds of the formula I according to Example 1 or combinations of these active compounds with other insecticides or acaricides (% = percent by weight):

0042<tables id="tabl0007" num="0007"><img file="EP0303570A2_D0016.tif" /></tables>

0043The active ingredient or combination of active ingredients is mixed with the additives and ground well in a suitable mill.

0044Spray powder is obtained which can be diluted with water to form suspensions of any desired concentration.

3.6. Emulsion concentrate

0045<tables id="tabl0008" num="0008"><img file="EP0303570A2_D0017.tif" /></tables>

0046Emulsions of any desired concentration can be prepared from this concentrate by dilution with water.<tables id="tabl0009" num="0009"><img file="EP0303570A2_D0018.tif" /></tables>

0047Ready-to-use dusts are obtained by mixing the active ingredient with the carrier and grinding it in a suitable mill.

3.8. Extruder granules

0048<tables id="tabl0010" num="0010"><img file="EP0303570A2_D0019.tif" /></tables>

0049The active ingredient or combination of active ingredients is mixed with the additives, ground and moistened with water. This mixture is extruded, granulated and then dried in an air stream.

3.9. Coating granules

0050<tables id="tabl0011" num="0011"><img file="EP0303570A2_D0020.tif" /></tables>

0051The finely ground active ingredient or combination of active ingredients is applied evenly in a mixer to the kaolin moistened with polyethylene glycol. In this way, dust-free coating granules are obtained.

3.10 suspension concentrate

0052<tables id="tabl0012" num="0012"><img file="EP0303570A2_D0021.tif" /></tables>

0053The finely ground active ingredient or combination of active ingredients is intimately mixed with the additives. This gives a suspension concentrate from which suspensions of any desired concentration can be prepared by dilution with water.

Example 4: Insecticidal contact effect: Aphis craccivora

0054Plants grown in pots (Vicia faba) are populated with about 200 individuals of the species Aphis craccivora before the start of the experiment. The plants treated in this way are sprayed 24 hours later with an aqueous preparation containing 400 ppm of the compound to be tested to runoff. Two plants are used per test compound and the kill rate achieved is evaluated after a further 24 hours.

0055Compounds of the formula I according to Example 1 show good activity (mortality) in this test.

Example 5: Insecticidal systemic activity: Aphis craccivora

0056Rooted bean plants are transplanted into pots containing 600 cc of soil. Then pour 50 ml of a preparation of the compounds to be tested (obtained from a 250% wettable powder) each in a concentration of 400 ppm directly on the earth in the pots.

0057After 24 hours, lice of the species Aphis craccivora are placed on the aerial parts of the plants and the plants are placed over them with a plastic cylinder in order to protect the lice from possible contact or gas effects of the test substance.

0058The killing achieved is evaluated 48 and 72 hours after the start of the test. Two plants, one in a separate pot, are used per test substance. The test is carried out at 25 ° C and 700/0 relative humidity.

0059The compounds of the formula I according to Example 1 show good activity in the above test.

Example 6: Insecticidal contact effect: Myzus persicae

0060Approximately 4 cm high pea seedlings, which are grown in water, are populated with approx. 200 individuals of the species Myzus persicae before the start of the experiment. The plants treated in this way are sprayed to dryness 24 hours later with an aqueous suspension containing 400 ppm of the compound to be tested. Two plants are used per batch. The kill rate achieved is evaluated 48 hours after application. The test is carried out at 20-22 ° C and 60% relative humidity.

0061The compounds of the formula I according to Example 1 show good activity in the above test.

Example 7: Insecticidal systemic action: Myzus persicae

0062Rooted cabbages in the 4- to 5-leaf stage are transplanted into pots that contain 60 cc of soil. 50 ml of an aqueous formulation of the compound I to be tested (obtained from a 250% wettable powder) are then poured directly onto the earth in a concentration of 400 ppm.

0063After 24 hours, aphids of the species Myzus persicae are placed on the aerial plant parts of the treated plants and the plants are covered with plastic cylinders in order to protect the aphids from possible contact or gas effects of the test substance.

0064The 0 / o kill achieved is evaluated 48 hours after the start of the test. Two plants, one in separate pots, are used per test substance. The test is carried out at approx. 25 ° C and 60% relative humidity.

0065The compounds of formula 1 according to Example 1 show good activity in the above test.

Example 8: Insecticidal leaf penetration activity: Aphis craccivora

0066A suitable small branch of Vicia faba, which is severely infected with aphids from the species Aphis craccivora, is placed in a plastic cup of about 8 cm (diameter about 6 cm). The cup is covered with a plastic lid, which has a punched-out opening of 2 cm in diameter in the middle. A leaf of a Vicia faba plant is placed on the opening in the lid without separating this leaf from the potted plant. The sheet is then fixed with a second perforated lid on the cup over the opening of the first lid. From the bottom, ie through the opening of the first cover, the aphids in the cup now infect the top leaf of the forage plant. On top of the sheet, an aqueous preparation of the active ingredient to be tested is applied evenly in a concentration of 400 ppm using a brush. It is checked whether the test substance applied on one side to the top of the leaf of the fodder plant diffuses through the leaf on its underside in sufficient quantity to kill sucking aphids there.

0067The test is carried out at about 20 ° C and 60% relative humidity. Evaluation for% mortality is carried out 48 hours after drug application.

0068Compounds of the formula according to Example 1 show good activity in the above test.

Example 9: Insecticidal activity (systemic water): Aphis craccivora

0069Pea seedlings that had been infested with the aphids 24 hours before the start of the experiment are placed in 20 ml of an aqueous broth containing 400 ppm of the active ingredient to be tested. The aqueous broth is made from an emulsion concentrate or a wettable powder preparation of the active ingredient in question and is located in a vessel that is closed with a plastic lid with holes. The root of the infested pea plant is pushed into the broth through a hole in the plastic lid. The hole is then sealed with cotton wool in order to fix the plant and to eliminate any influence of the gas phase from the broth.

0070The test is carried out at 20 ° C and 60 ° C relative humidity. After two days, the number of test animals which are no longer absorbent is assessed in comparison with untreated controls. This determines whether the active ingredient absorbed through the root kills the aphids on the upper parts of the plant.

0071In the above experiment, compounds of the formula I according to Example 1 show a good systemic action against insects of the species Aphis craccivora.

Example 10: feeding poison and contact effect on Laodelphax striatellus and Nilaparvata lugens (nymphs);

0072The test is carried out on growing plants. To do this, 4 rice plants (stem thickness 8 mm) with a height of approx. 20 cm are planted in pots (diameter 8 cm).

0073The plants are sprayed on a turntable with 100 ml of an acetone solution containing 400 ppm of the respective active ingredient. After the spray coating has dried on, each plant is populated with 20 nymphs of the test animals in the third stage. In order to prevent the cicadas from escaping, a glass cylinder, which is open on both sides, is put over the populated plants and covered with a gauze cover. The nymphs are held on the treated plant for 10 days until the following developmental stage is reached. Evaluation for% mortality takes place 1, 4 and 8 days after the treatment. Compounds of formula 1 according to Example 1 show good activity in this test against Nilaparvate lugens.

Example 11: Systemic effect on Nilaparvata lugens

0074Rice plants about 10 days old (approx. 10 cm high) are placed in a plastic beaker which contains 20 ml of an aqueous emulsion preparation of the active ingredient to be tested in a concentration of 400 ppm and is closed off with a plastic lid having holes. The root of the rice plant is pushed through a hole in the plastic lid into the aqueous test preparation. The hole was then sealed with cotton wool to hold the plant in place and eliminate the influence of the gas phase from the test preparation. Then the rice plant is populated with 20 nymphs from Nilaparvata lugens in the N 2 to N 3 stage and covered with a plastic cylinder. The test is carried out at 20 ° C and 60% relative humidity with an illumination period of 16 hours. After five days, the number of test animals killed is compared to untreated controls. This determines whether the active ingredient absorbed through the root kills the test animals on the upper parts of the plant. Compounds of the formula I according to Example 1 show good activity (mortality) against Nilaparvata lugens in the above test.

Example 12: Insecticidal food poison and contact effects

0075Approx. 25 cm high potted cotton plants are sprayed with aqueous active substance emulsions which contain the active substance in a concentration of 800 ppm.

0076After the spray coating has dried on, the cotton plants are colonized with Spodoptera littoralis or Heliothis virescens larvae in the first larval stage. The test is carried out at 24 ° C and about 60% relative humidity. After 120 hours, the% mortality of the test insects compared to untreated controls is determined.

0077Compounds of the formula I according to Example 1 show good activity (mortality) in this test.

Example 13: Action against Nephotettix cincticeps (nymphs)

0078The test is carried out on growing plants. For this purpose, rice plants about 20 days old and about 15 cm high are planted in pots (diameter 5.5 cm).

0079The plants are sprayed on a turntable with 100 ml of an acetone solution containing 400 ppm of the active ingredient to be tested. After the spray coating has dried on, each plant is populated with 20 nymphs of the test animals in the second or third stage. In order to prevent the cicadas from escaping, a plexiglass cylinder is placed over each of the populated plants and covered with a gauze cover. The nymphs are held on the treated plant for 5 days, which must be watered at least once. The test is carried out at a temperature of approx. 23 ° C., at 55% relative atmospheric humidity and with an exposure period of 16 hours. Compounds of formula 1 according to Example 1 show good activity in this test.