DD285277A5 - SCHAEDLINGSBEKAEMPFUNGSMITTEL - Google Patents

Abstract

The present invention relates to pesticides having fungicidal, insecticidal, ectoparasiticidal or herbicidal activity. The compositions according to the invention are characterized in that they contain as active ingredient a compound of general formula I in which W, D, R 1, R 2, R 3, X, m, n and p are as defined in the description, in addition to one for agriculture suitable dismutating agent and / or carrier agent. Formula I {pesticide; active ingredient; Connection; Grouping; Verduennungsmittel; Traegermittel}

Description

R ^{4 represents} an alkyl group or a bond attached to R ¹ and the ring D is optionally substituted, and addition compounds of compounds which are basic with acids and addition compounds with bases of compounds which are acidic, in an agriculturally suitable diluent and / or carrier.

2. Composition according to claim 1, characterized in that n = 1, p = 1, m = 0, W is a CH group or N, R ² and R ^{3 are} methyl groups, XS and R ^{1 is} a Heteroarylradikal.

3. A method for controlling pests in a place that is infected with or can be infected with it, characterized in that a compound which has been claimed in a claims 1 and 2 is applied to this location.

Field of application of the invention

The present invention relates to pesticides having fungicidal, insecticidal, ectoparasiticidal or herbicidal activity.

Characteristic of the known state of the art

Derivatives of acrylic acid having fungicidal activity have recently been described in a number of publications, in particular in EP 178,826 and 203,608.

Object of the invention

The compounds used according to the invention have an improved action than the compounds known from the prior art.

Explanation of the essence of the invention

The invention has for its object to provide new pesticides available. The invention relates to pesticides containing as active ingredient

o = _O / N /

in which either

A) W means a grouping CQ in which either

a) Q is hydrogen, R ^{3 is} hydrogen or an alkyl group, ρ = 1und

(i) η = 1, m = 0, X = S, O, SO, SO ₂ , NR ⁴ , Si (OR ² JR ² , Si (R ² J ₂ or Si (OR ² J _{2 in} R ¹ is R) ^s is wherein R ^{5 is} an optionally substituted heteroaryl radical, an optionally substituted heterocyclic radical, an optionally substituted heterocyclic (thio) carbonyl radical, an optionally substituted alkenyl radical, an optionally substituted alkynyl radical, an optionally substituted N-substituted iminomethylene radical, a substituted heterocyclylidenemethyl radical;

(U) η = 0, m = 1 to 18, X is S and R ¹ is R ⁵ or an optionally substituted aryl radical, or

b) Q and R ^{3 form} part of a five- or six-membered ring which may be substituted and may contain other heteroatoms, in particular nitrogen, ρ = 0 or 1, m and η are 0 to 18, at least one of the indices m, η and ρ is greater than 0, X is S, SO, SO ₂ , NR ² , Si (OR ² JR ² , Si (R ² J ₂ or Si (OR ² J ₂ and R ¹ is R ⁶ or hydrogen or an optionally substituted Alkyl radical or an optionally substituted aryl radical, or

B) WN in which case R ^{3 is} hydrogen or an alkyl group, m is 0, ρ and η are 1, X is O, S, NR ² , Si (OR ² IR ² , Si (R ¹ J ₂ or Si ( OR ² J ₂ and Π ¹ is R ⁶ ,

R ^{2 represents} an alkyl group,

R ^{4 is} an alkyl group or a bond bonded to R ¹ , and D ring optionally substituted, and the addition compounds (salts) with acids of the compounds which are basic and addition compounds with bases of the compounds which are acidic , in addition to an agriculturally suitable diluent and / or carrier.

The compounds used in the invention exist as structural isomers and the invention includes the individual isomers as well as mixtures thereof.

The alkyl groups preferably have 1 to 4 carbon atoms and are especially the methyl and ethyl group. Alkenyl and alkynyl groups generally have three to six carbon atoms. Substituents optionally present on an alkyl, alkenyl or alkynyl group include halogens, alkoxy groups (e.g., having 1 to 4 carbon atoms), haloalkoxy groups (eg, difluoromethoxy groups), hydroxyl groups, alkylthio groups, nitro groups, optionally substituted amino groups, carboxy groups, Alkoxycarbonyl groups, cyano groups, acyloxy groups and aryl radicals. Aryl groups are usually phenyl groups, which may be replaced by, for. As halogens, optionally substituted alkyl or alkoxy groups, aryl radicals, aryloxy radicals, nitro groups, amino groups, COOH, COOR ² , CN, CONR ² R ² or S (O) _n R ^{2 are} substituted. The terms "heteroaryl" and "heterocyclic" include groups such as thienyl, furyl, pyridyl, pyrimidyl, pyrazolyl, thiazolyl, thiazolinyl, thiazolone, oxazolyl, benzimidazolyl, tetrazolyl, benoxazolyl, thiadiazolyl, , Dioxolanyl, imidazopyridinyl, 1,3-benzoxyzinyl, 1,3-benzthiazinyl, oxazolpyridinyl, triazolyl, triazinyl, imidazolyl, morpholino, benzfuranyl, pyrazolinyl, quinolinyl, quinazolinyl, dihydroquinazolinyl or benzothiazolyl groups, which themselves may be substituted, e.g. B. as the phenyl groups above. Ring D may be substituted in a similar manner as has been described for phenyl groups, but also by carboxy, alkoxycarbonyl, sulfonyl and sulfonamide groups.

The term "acyl" includes as well as the radicals of the carboxylic acids the acids containing the sulfone and the phosphorus Acyl groups are preferably alkanoyl groups, eg having 1 to 4 carbon atoms Amino groups may be substituted, for example by one or two alkyl groups, or two substituents iminomethylene groups may be substituted on both the nitrogen atom and carbon, and examples of substituents on the nitrogen atom include aryl and alkyl groups, examples of which are substituents on the carbon atom are aryl, alkyl, Alkylthio, alkoxy and cyano groups.

A particularly preferred group of compounds is that in which η is 1, ρ is 1, m is O, W is CH or N, R ² and R ^{3 are} methyl groups, X is S and R ^{1 is} a heteroaryl radical.

The compounds used in the invention are particularly valuable as fungicides, especially against plant diseases caused by fungi, e.g. As powdery mildews and especially downy mildew (Erysiphe graminis), wine powdery mildew (Plasmopara viticola), rice blast (Pyricularia oryzae), culmination disease (Pseudocercosporella herpotrichoides), rice hull brandy (Pellicularia sasakii), gray mold (Botrytis cinerea), whitish (Rhizoctonia solani), brown rust (Puccinia recondita), late blight (Phytophtors infestans) and apple scab (Venturia inaequalis). Other fungi against which the compounds of the present invention are effective include, but are not limited to, other mildews, other rust diseases and in general pathogens of Deuteromycetes, Ascomycetes, Phycomycetes and Basidomycetes. The compounds used in the invention also have activity as insecticides, acaricides and nematicides and are particularly suitable for controlling a number of economically important insects, acarids and plant nematodes, including ectoparasites of animals and in particular Diptera, z. B. blowflies (Lucilia sericata), and common houseflies, Musca domestica; Lepidoptera, including Plutella xylostella, Spodoptera littoralis, Heliothis armigera and Pieris brassicae; Homoptera, including aphids such as Meguora viciae; Coleoptera, including the cereal rootlets (Diabrotica spp., E.g., Diabrotica and ecimpunctata); and spider mites such as Tetranychus spp. They may also have efficacy as a herbicide. Thus, this invention also provides a method of controlling pests (ie fungi, insects, nematodes, acarids and weeds) at the affected site or at the site that may be affected by it, which is at this site Compound of formula I apply.

Of course, the compositions according to the invention may contain more than one compound used according to the invention. In addition, the composition may contain one or more additional active ingredients, e.g. B. Compounds which are known to have the properties of plant growth regulator, herbicide, fungicide, insecticide or acaricide. Alternatively, the compounds of the invention may be used in sequence with the other ingredients.

The diluent or carrier in the composition according to this invention may be a solid or a liquid, optionally together with a surfactant, e.g. A dispersant or a wetting agent. Suitable surfactants include anionic compounds such as carboxylates, e.g. As a Metallcarboxylct a long-chain fatty acid, an N-acyl sarcosinate, mono- or diesters of phosphoric acid with fatty alcohol ethoxylates or the salts of these esters, fatty alcohol sulfates, z. Sodium dodecylsulfate, sodium octadecylsulfate or sodium cetylsulfate; ethoxylated fatty alcohol sulfates, ethoxylated alkyl phenyl sulfates, lignosulfonates, petroleum sulfonates, alkyl aryl sulfonates such as alkylbenzenesulfonates or lower alkylnaphthalenesulfonates, e.g. As butylnaphthalenesulfonate, salts of sulfonated naphthalene-formaldehyde condensation products or more complex sulfonates such as amidesulfonates, z. As the sulfonated condensation product of oleic acid and N-methyl aurin or dialkylsulfosuccinates, z. For example, the sodium salts of the sulfonation of the succinic acid dioctyl ester. Nonionic surfactants include condensation products of fatty acid esters, fatty alcohols, fatty acid amides or long chain alkyl or alkenyl substituted phenols with ethylene oxide, fatty acid esters of ethers of polyhydroxy compounds, e.g. B. sorbitol fatty acid esters, condensation products of such esters with ethylene oxide, for. For example, polyoxyethylene sorbitol fatty acid esters, block copolymers of ethylene oxide and propylene oxide, acetylenic glycols such as 2,4,7,9-tetramethyl-5-decyne-4,7-diol or ethoxylated acetylenic glycols. Examples of cationic surfactants include, among others, e.g. Aliphatic mono-, di- or polyamines as their acetates, naphthenates or oleates, oxygen-containing amines such as amine oxides or a polyoxyethylene alkylamine, amide-linked amine prepared by the condensation of a carboxylic acid with a di- or polyamine, or a quaternary ammonium salt.

The compositions of the invention may have any form known in the art for the formulation of agrochemicals, e.g. For example, they may be in the form of solutions, dispersions, aqueous emulsions, dusting powders, seed dressings, fumigants, smoke-generating agents. Bait, dispersible powders, emulsifiable concentrates or granules.

In addition, they may be in a suitable form for direct use or as a concentrate or as primary compositions requiring dilution with an appropriate amount of water or other diluent prior to use.

An emulsifiable concentrate consists of a compound used according to the invention, which is dissolved in a water-immiscible solvent, and this solution is converted into an emulsion by mixing with water in the presence of an emulsifier.

A dusting powder consists of a compound used according to the invention, with a solid, powdery diluent, for. B. kaolin, has been mixed and ground.

A granulate consists of a compound used according to the invention, which is combined with similar diluents as those which can be used for the dusting powders, but this mixture is granulated by known methods. On the other hand, it may be that the active ingredient is applied to a previously granulated diluent, e.g. As fuller earth, attapulgite or limestone shot, is absorbed or adsorbed. .

Wettable powders, granules or granular material usually consists of the active ingredient together with a suitable surfactant and an inert powdered diluent, e.g. B. China earth. Another suitable concentrate is a flowable suspension concentrate which is prepared by milling the active compound with water or other liquid, a wetting agent and a suspending aid. The concentration of the active ingredient in the compositions of the invention, when applied to plants, is preferably in the range of 0.001 to 3.0% by weight, in particular in the range of 0.01 to 1.0% by weight. In a primary composition, the amount of active ingredient may vary widely and may be e.g. B. be between 5 and 95Gew .-% of the composition.

In the process according to the invention, the active compound is generally applied to seeds, plants or the place where they are located. Thus, the active compound can be applied directly to the soil before or after sowing or during sowing, so that the presence of the active compound in the soil can control the growth of fungi that can attack the seed. If the soil is treated directly, the active compound can be applied in any manner which ensures intimate mixing with the soil, e.g. By spraying, by spreading a solid form of granules or by applying the active ingredient at the same time as

sowing is done by adding it to the seed. An appropriate amount for application is between 0.05 and 20kg / ha, preferably between 0.1 and 1kg / ha. On the other hand, the active compound can be applied directly to the plant, e.g. By spraying or dusts, either at the time when the fungus begins to appear on the plant or before the fungus appears as a protective measure. In both cases, the preferred embodiment is spraying the foliage. It is generally important to ensure good fungus control at an early stage of plant growth, as this is the time when the plant can be most severely damaged. The spray or dusting powder may further contain a herbicide which is effective before or after the sowing of the seed, if considered necessary. Sometimes it is convenient to treat the roots of a plant before or during planting, eg. B. by dipping the roots in a suitable liquid or solid composition. When the active compound is applied directly to a plant, a suitable use concentration is in the range of 0.01 to 10 kg / ha, preferably between 0.05 and 5 kg / ha.

The compounds used in the invention can be prepared on a variety of synthesis routes, for. B. by reacting a compound of formula (II)

Z- (CHp) _n "

^{2 n} '(ID,

OR "in which Z is a leaving group, for example halogen, with a compound of the formula (III)

R '- (CH ₂ ) _m -X _p -H (III)

On the other hand, when W is a CH group, a compound of the formula (IV)

R ¹ - (CH ₂ ) _m - X - (CH ₂

with a formic acid ester of the formula (V)

HCOOR ² (V)

be reacted under basic reaction conditions.

Compounds in which X represents SO or SO ₂ may be obtained by oxidation of compounds in which X is S, using a suitable oxidizing agent, e.g. As m-chloroperbenzoic acid is used. Other methods are known to the chemist familiar with the art, as well as methods for making the starting materials and intermediates. The examples also describe a number of methods for the preparation of compounds used according to the invention and of starting materials and intermediates.

This invention will be explained by the following embodiments. The structures of the new compounds were confirmed by elemental and / or other suitable analytical methods. The temperatures are given in ° C.

Ausführungsbeispiole

example 1

100 g of methyl o-tolylacetate were dissolved in a mixture of 450 ml of methyl formate and 200 ml of dimethylformamide. This solution was added with cooling to a suspension of sodium hydride (from 36.5 g of an 80% dispersion in oil) in 100 ml of dimethylformamide. The mixture was then stirred at room temperature overnight. The excess formic acid methyl ester and the bulk of the dimethylformamide were evaporated and 500 ml of water added. This mixture was added with ether and the aqueous phase separated, acidified and extracted with ether. The extract was worked up in the usual way to obtain a brown oil. This was dissolved in tetrahydrofuran and the solution added dropwise to sodium hydride (16.5 g of an 80% dispersion in oil) in 50 mL of tetrahydrofuran with cooling. When no more hydrogen is evolved, 35 ml of methyl iodide are added and the mixture is refluxed for 5 hours. Then, 5 ml of methanol are added and the solvent evaporated. The resulting oil was then ether-water extracted and the organic phase was worked up in the usual manner to give methyl (Z) -3-methoxy-2- (o-tolyl) propenoate, F = 68-70 ° C , was received. 185g this

Product were dissolved in 1250ml carbon tetrachloride, added 159.3g N-bromosuccinimide and the mixture was refluxed for 3 hours. Thereafter, the reaction mixture was cooled and worked up to obtain a brown oil. The crude product was slurried with a 10% solution of diisopropyl ether in petroleum ether to give (E) -3-methoxy-2- | (2-bromomethyl) phenyl] -propene-carboxylic acid methyl ester, F = 87-90 ° C. 101.87 g of mercaptobenzothiazole in 600 ml of tetrahydrofuran were added dropwise with stirring to a suspension of sodium hydride washed with petroleum ether (from 18.42 g of an 80% dispersion in oil) in 200 ml of tetrahydrofuran. The mixture was refluxed for 30 minutes and then cooled to room temperature. A solution of 175 g of the bromomethyl compound in 1000 ml of tetrahydrofuran was added over one hour and then the mixture was stirred at room temperature for five hours. Subsequently, hydrous tetrahydrofuran was added to stop the reaction, and finally the mixture was evaporated. The residue was worked up in the usual manner to give (E ^ -fa ^ -BenzthiazolyDthiol-methyll-phenyll-S-methoxy ^ propanoate, F 77-78 ⁰ C (compound 1) was obtained =.

Example 2

25 g of potassium carbonate were added with stirring to a solution of 7.5 g of O-toluenoic acid in 125 ml of aceto tril. This mixture was stirred at room temperature for 10 minutes. Thereafter, 6.13 g of ethyl chloroacetate were added and the mixture was refluxed overnight. It was then poured into water, acidified to pH 2 with concentrated hydrochloric acid and extracted with ethyl acetate. The extract was washed with brine, dried and evaporated. By purification by column chromatography, O-tolylacetylethoxycarbonylmethyl ester was obtained. To a solution of 'Og this product in 100ml dimethylformamide 15g potassium carbonate were added with stirring. The mixture was stirred at room temperature for 72 hours and then refluxed overnight. The mixture was then cooled to ⁰ ° C. and 5 g of potassium carbonate added, finally 2.65 ml of methyl iodide were added. This mixture was stirred at room temperature for 24 hours. The mixture was then poured into water, extracted with ether and the extract washed with brine, dried and evaporated to give 3- (2-methylphenyl) -4-methoxy-furan-2 (5H) -one as a gum. This was then treated with N-bromosuccinimide and reacted with 2-mercaptobenzothiazole as described in Example 1 to give 3 - [- 2 # (2-benthiazolyl) thio] methyl] -pher-1-yl-4-methoxy. furan-2 (5H) -one, F = 81-82 ° C (Compound 2).

Example 3

6 g of benz [b] thiophene-2 (3H) -one and 3.2 g of sodium hydroxide were boiled in 40 ml of water for one hour at reflux. To this was added 6.44 g of 4-chlorobenzyl chloride and this mixture was boiled for a further 1 1/2 hours at reflux, then allowed to cool overnight. 25 ml of water and then 100 ml of acetic acid were added. The resulting solid was filtered, washed with water and dried to give 2- 2- (4-chlorobenzylthio) phenyl-1-acetic acid, F = 149-151 ° C. A solution of 10.4 g of this product in 250 ml of methanol, refluxed overnight and then excess methanol was evaporated off, ether and water were added to the residue and the organic phase was washed with sodium hydroxide solution, dried and evaporated The product which solidified became hexane recrystallized, whereby the Methylester of the acid used as a starting point was obtained, m.p. = 52-54 ⁰ C. This was reacted with methyl formate and sodium hydride in a similar manner as has been described in the procedure in example 1, to give (e ) -3-methoxy-2- (2- (4-chlorobenzylthio) phenyl] prop-2-enoate, m.p. = 81-84 ⁰ C, compound 3, and the corresponding Z-isomer, m.p. = 127-128 ⁰ C. (Compound 4) were obtained, which were separated by chromatography on silica gel.

Example 4

22.5 ml of methyl chloroacetate In 60 ml of tetrahydrofuran were added dropwise within one hour with stirring to a solution of 33.35 g of imidazole in 500 ml of tetrahydrofuran, which was kept at ⁰ ° C. and under a nitrogen atmosphere. This mixture was then stirred for an additional hour at this temperature. The reaction mixture was filtered and the precipitate washed with tetrahydrofuran. The filtrate and washings, the a-oxo-1 H-imidazol-1-acetic acid methylester were contained, cooled to -65 ⁰ C and the solution of a Grignard reagent selected from 42g o-bromotoluene, 3.6 ml of dibromomethane and 7g Magnesium in tetrahydrofuran was added over 45 minutes while maintaining the temperature between -60 and -70 ° C. The mixture was then stirred at this temperature for 15 minutes and at room temperature for 2 1/2 hours. Thereafter, it was poured into ice / water mixture, extracted with ether, the extract washed with brine, dried and concentrated. The residue was distilled under reduced pressure to give oxo (o-tolyl) acetic acid methyl ester, kp = 92-97 ° C / 0.5mm. A solution of 5 g of this product in 100 ml of methanol was refluxed for three hours together with 2.55 g of methoxyamine hydrochloride. The mixture was then cooled, evaporated, slurried with diisopropyl ether, filtered and the filtrate evaporated to give (methoxyimino) -o-tolyl-acetic acid methyl ester. This was then reacted with N-bromosuccinimide in carbon tetrachloride and the addition of benzoyl peroxide (0.005g every 10 minutes) on reflux and exposure to a 300 watt lamp. Conventional work-up gave the bromomethyl compound, which was then reacted with 2-mercaptobenzothiazole in a similar manner as described in Example 1 to give [-2- (2-benzthiazolyl) thio] methyl] phenyll - (methoxyimono) -acetic acid methyl ester, F = 113-114 ⁰ C (compound 5) was obtained.

In a similar manner as described in one of the preceding examples, the following compounds were prepared: Unless otherwise noted, the said compounds are in the E-form.

R ¹ - (CH ₂ ) _m -X - (CH ₂ ) _n

MeOC

CH-OMe

No. of the R ¹ Xp m η FCC) connection 6-EtO-benzothiazol-2-yl S O 100-101 6 benzoxazol-2-yl S O oil 7 1-Me-imidazol-2-yl S O 102-104 8th 4-Me-pyrimidin-2-yl S O 94-95 9 4,6-Me ₂ -pyrimidin-2-yl S O oil 10 4-Bu'-1H-imidazol-2-yl S O glass 11 (MeS) (3-Me-5-oxo-1-Ph-pyrazolin-4-ylidine) methyl S O 129-1Ϊ1 12 pyrimidin-2-yl S O 75-76 13 2-thiazolin-2-yl S O 105-106 14 5-MeCO-benzothiazol-2-yl S ο · 109-110 15 Ph (Z isomer) S I D 92-4 16 5-CF ₃ -benzimidazul-2-yl S O oil 17 i-Ph-tetrazol-5-yl S O 126-127 18 5-CF ₃ -benzothiazol-2-yl S O 97-99 19 Ph S I D 71-74 20 4,4-ME2-5-methylene-2-thiazolin-2-yl S O 101 21 5-Ph-pyrimidin-2-yl S O 105-106.5 22 6-CI-4-Me-benzothiazol-2-yl S O 89-91 23 5-Me-benzothiazol-2-yl S O 83-85 24 5-aminobenzothiazol-2-yl S C gum 25 4-CI-benzothiazol-2-yl S O 152-154 26 2-pyridyl S O 80-82 27 1- (3-NO ₂ -Ph) tetrazol-5-yl S O 93-95 28 2-thienyl S O 64-65 29 5-Me-benzoxazol-2-yl S O 90-91 30 S-CN ^ -COOEt-e-pyridyl Me ^ S O 113-114 31 7-CI-benzothiazol-2-yl S O 132-134 32 5,6-Cl ₂ -IH-benzimidazol-2-yl S O 169.5-171 33 5-CI-benzoxazol-2-yl S O 105-107 34 6-CI-benzothiazol-2-yl S O 110-112 35 1 -MeS-2-CN-2-COOMe-vinyl S O 85-85 36 5- (2-N0 ₂ -benzylidene) -4-oxo-2-thiazolin-2-yl S O 177-178.5 37 4-OH-5-Me-6-Pr-pyrimidin-2-yl S O 169-170 38 imidazo (1,5-a) pyridin-3-yl S O 77-79 39 4-Ph-thiazol-2-yl S O oil 40 5-propargylthio-1,3,4-thiadiazol-2-yl S O oil 41 3-CN-4,6-Me ₂ -2-pyridyl S O 140-142 42 3 MoO-Ph   s I O 87-89 43 3-MeO-Ph (Z isomer) S I O 95-97 44 1-Pr-benzimidazol-2-yl S O 68-70 45 4-Ph-Bu' S I D oil 46 4-pyridyl S O 101-103 47 l-benzylthio-2,2-dicn-vinyl S O 97-93 48 1 -Me-5-MeS-benzimidazol-2-yl S O 90-92 49 1-Ph-1,2,4-triazol-3-yl S O oil 50 1 -Pr'-benzimidazol-2-yl S O oil 51 5-Br-benzothiazole-2-yl S O 124-124.5 52 5-Br-1H-benzimidazol-2-yl S O 179-180 53 2,2-Me ₂ -1,3-dioxolan-4-yl S 1 D oil 54 2,2-Me ₂ -1,3-dioxolan-4-yl (Z isomer) S 1 O oil 55 Ph S 2 O oil 56 Ph (Z isomer) S 2 O oil 57 7-CI-4-MeO-benzothiazol-2-yl S O gum 58 1H-benzimidazol-2-yl S O 166-168 59 5-CI-benzothiazol-2-yl S O 109-110 60 5-NO ₂ -benzoxazol-2-yl S O 120-122 G1

No. of the R ¹ Xp m Π F ( ⁰ C) connection 5-t-Bu-benzoxazol-2-yl S O 85-87 62 5-EtS-1-Me-benzimidazol-2-yl S O gum 63 4,6,7-CI ₃ -benzothiazol-2-yl S O 159-161 64 5-Ph-thiazol-2-yl S O oil 65 5,7-Me ₂ -benzoxazol-2-yl S O 97-98 66 6-Me-benzoxazol-2-yl S O 70-73 67 morpholinothioxomethyl S O 97-99 68 4-CI, 3-MeO-Ph S I D oil 69 1,2,4-triazol-l-yl S I 0 oil 70 3-MeO-Ph S 2 0 oil 71 5,7-CI ₂ -2,3-dihydrobenzofuran-2-yl S I 0 oil 72 Ph-CH = CH S I 0 oil 73 1,2,4-triazin-3-yl S O 163 74 pyrimidin-4-yl S O 101 75 2-Me-1,3-dioxolan-2-yl S I 0 oil 76 6-Pf-benzothiazol-2-yl S O oil 77 6-PhO-benzothiazol-2-yl S O 124-126 78 ö-MeCONH-benzothiazol-2-yl S O 151-153 79 4-Ph-Ph S I D 131-133 80 Bu'-C ^ C S 2 0 76-77 81 Bu'-CsC (Z-isomer) S 2 D oil 82 4- (4-CI-PhO) -Ph S I 0 109-113 83 3-pyridyl S I 0 oil 84 4-oxo-3,4-dihydropyrimidine-2-yl S O 163 85 5-PhCONH-benzothiazol-2-yl S O 100 86 5- (1,3-benzodioxol-5-yl-methylene-amino) benzothiazol-2-yl S O foam 87 4-oxo-3,4-dihydroquinazoline-2-yl S O 223-226 88 quinolin-2-yl S O 88-90 89 3-Me-benzothiazol-2 (3H) -ylidine N = O 139-141 90 4- {4-CI-PhO) -Ph (Z-isomer) S I 0 148-151 91 5-Ph-1,2,4-triazin-3-yl S O 167 92 3-Ph-1,2,4-thiadiazol-5-yl S O oil 93 2-Ph-1,3-dioxolan-2-yl S I 0 oil 94 2-Ph-1,3-dioxolan-2-yl (Z isomer) S I 0 120-122 95 5-PhCH = N-benzothiazol-2-yl S O gum 96 5-PhN = CH (MeS) S O gum 97 4-CI-Ph) -thiazol-2-yl, 4- S O 99-102 98 4- (4-Me-Ph) -thiazol-2-yl S O gum 99 5-Me-4-Ph-thiazol-2-yl S O 88-91 100 5-Cl-1-H-benzimidazol-2-yl S O 161-164 101 3-Me-4-oxo-3,4-dihydroquinazoline-2-yl S O 144-146 102 4-Me-Ph-5-thiazol-2-yl S O oil 103 2H-1,4-benzcthiazin-3-yl S O oil 104 2-H-1,4-benzoxazin-3-yl S O oil 105 6-CI-oxazolo (4,5-b) pyridin-2-yl S O 114-116 106 5-Cl-1-Me-benzimidazol-2-yl S O 132-135 107

In a similar manner as described in Example 4, the following compounds were prepared:

R ¹ - (CH ₂ ) _m -X - (CH ₂ ) _n

No. of the connection

Meogo

N-OMe

R ¹

F (O

5-chloro-benzthiazol-2-yl benzoxazol-2-yl

O O

110-111 111-113

Also, in a similar manner as described in Example 2, 4-methoxy-3- [2- (phenylthiomethyl) -phenylfuran-2 (5H) -one (Compound 110) was prepared.

Example 5

This example illustrates the preparation of typical concentrates which can be prepared from the compounds used according to the invention:

a) Wettable powders 25Gew .-% According to the invention used compound 5 wt .-% sodium lignosulfonate 5 wt .-% silica gel 65Gew .-% kaolin b) Emuiglerfählges concentrate 250g / l According to the invention used compound 200g / l Soprophor BSU ' 657 g / l N-Mothylpyrrolidon

Tristyrylphenol ethoxylate, nonionic emulsifying agent.

Test Example A The compounds used according to the invention were used in one or more of the following ways with regard to their Effectiveness examined:

a) Leaf tests

Phytophtora infestans: cabbage rot in tomatoes (Pl) Plasmopara viticola: downy mildew (PV) Erysiphe graminis: Mildew (EC) Pyricularia oryzae: Rice Flame (PO) Pellicularia sasakii: rice hull spirit (PS) Botrytis cinerea: gray horse (BC) Venturia inaequalis: apple scab (Vl) Puccinia recondita: Brown rust (PR) Aqueous solutions or dispersions of the compounds of the desired concentration, including a wetting agent,

were applied by means of the spray or impregnation Tochnik the stem base of the plants to be examined. These plants were then infected with the appropriate pathogens and kept under controlled conditions suitable for ensuring plant growth while developing the disease. After an appropriate time, the extent of infection on the leaf surfaces was visually determined.

The compounds have been classified as active if they cause more than 50% control of the disease Concentration of 125ppm (w / v) or below.

b) investigation of soil pathogens

In this study, the compound to be tested was tested for its effectiveness against Rhizictonia solani (R). Flasks with a mixture of maize flour and sand were infected with the fungus to be examined and then incubated. The cornmeal sand cultures were used to infect plant compost, which was then placed in plastic pots. Aqueous solutions or dispersions of the compounds including a wetting agent were added to the pots so that in each pot the desired concentration of the compound was adjusted. Control pots were also provided by adding similar solutions or dispersions but without the compound to be tested. Immediately after the addition of the compound to be tested, a number of cabbage seeds were sown in each pot. The seeds were covered with treated, infected soil and the pots were incubated under controlled environmental conditions suitable for plant growth and development of the crane. The number of risen cabbage seedlings is counted and the percent disease control calculated by comparing to the untreated, infected pots. The compounds are considered to be effective if they have given more than 50% control of the disease at a concentration of 100 parts by weight of compound or less per million parts by volume of soil

 The activities were determined as follows: (+ - active).

No. of the

Connection PI PV EG PO HS BC VI RS PR

2 +

4 +

8 +

II +

12 + +

No. of the

Connection Pl PV EG PO PS BC Vl RS PR_

16 + +

17 + +

18 +

20 ++ +

28 +++

33 +++

36 + +

37 +

38 +

39 +

41 + +

44 + +

46 + +

48 +

50 + +

51 +++

53 + +

56 + +

57 + +

59 + +

61 + + +

63 +

64 +

65 +++

67 +++

69 +

70+

71 +

74 +

75+

79 + +

80 + +

81 +++

82 +++

83 +

101 + +

Investigation Example B

This example illustrates the insecticidal activity of compounds used according to the invention,

1 ml aliquots of solutions of the compounds of various concentrations in acetone to be tested were placed on rolls of cotton wool for dental purposes contained in glass ampoules of 2 cm diameter and 5 cm length. After drying, the treated fabrics with 1 m! soaked in a nutrient solution, infected with larvae of the first stage of the blowfly (Lucilia sericata), closed with cotton wool stoppers and kept at 25 ° C. for 24 hours. In controls, mortality was less than 5%, while the compounds of Examples 6, 13, 15, 19, 21-24, 30, 32, 34, 35, 40, 49, 52, 60 and 61 had an LCw of less than 300ppm.

Claims (1)

1. pest control agent, characterized in that it is a compound of the general formula I as the active ingredient ν: in which either A) W means a grouping CQ in which either a) Q is hydrogen, R ^{3 is} hydrogen or an alkyl group, ρ = 1 and i) η 1, m O, XS, O, SO, SOj, NR ⁴ , Si (OR ² JR ² , Si (R ² J ₂ and R ¹ R ⁵ , where R ^{6 is} an optionally substituted heteroaryl radical, an optionally ' substituted heterocyclic radical, an optionally substituted heterocyclic (thio) carbonyl radical, an optionally substituted alkenyl radical, an optionally substituted alkynyl group, an optionally substituted N-substituted iminomethylene radical, a substituted heterocyclylidenemethyl radical or
ii) η = O, m = 1 to 18, XS and R ¹ R ⁵ or an optionally substituted aryl radical or b) Q and R ³ represent part of a five- or six-membered ring which may be substituted and may also contain other heteroatoms, in particular nitrogen, ρ = or 1, m and η = 0 ^ is 18, at least one of Sizes m, η or ρ is greater than 0, in which X is S, O, SO, SO ₂ , NR ² , Si (OR ² JR ² , Si (R ² J ₂ or Si (OR ² J ₂ and R ¹ R ⁵⁾ or wherein R ^{1 is} hydrogen or an optionally substituted alkyl or optionally substituted aryl group; B) WN means, in which case R ^{3 is} hydrogen or an alkyl group, m = O, ρ and η = 1, X is O, S, NR ² , Si (OR ² ) R ² , Si (R ² J ₂ or Si (OR ² J ₂ and R ^{1 is} R ⁵ , R ^{2 is} an alkyl group