DE2626967A1 - Naphtho-isothiazole - for use as an agricultural nematocide - Google Patents

Abstract

Naphth 2,1-d isothiazole, of formula (I), is a new cpd: Cpds. (I) is active against a wide range of plant-parasitic nematodes, including root knot eelworms, cyst eelworms, stem and leaf eelworms and soil nematodes, and is practically non-phytotoxic. In an example, (I) was prepd. by reacting 1-chloro-2-formylnaphthalene with S and NH3.

Description

Nematicide

The invention relates to naphth [2,1-d] isothiazole of the formula and nematicides containing naphth [2,1-d] isothiazole as an active ingredient.

It has been found that naphth [2,1-d] isothiazole is excellent nematicidal effect, for example against plant-parasitic root knot nematodes, Shows cyst tubules, stick and leaf tubules. This effectiveness is therefore special surprising, since the compound has no similarity in its chemical structure with known nematicidal active ingredients. Compared to known active ingredients Isothiazole has the particular advantage that it is hardly toxic and that it is well tolerated by plants has naphthL2,1-djisothiazole can according to the DT-PS 1 670 196 and in the Patent application P 25 03 699.1 described process by reacting 1-halo-2-dihalomethylnaphthalene or 1-halo-2-formylnaphthalene made with elemental sulfur and ammonia will.

Naphth 2,1-dcl isothiazole is effective against nematodes, for example Root knot nematodes, e.g. Meloidogyne incognita, Meloidogyne hapla, Meloidogyne javanica, cyst-forming nematodes, e.g. Heterodera rostochiensis, Heterodera schachtii, Heterodera avenae, Heterodera glycines, Heterodera trifolii, stick and leaf elbows, e.g. Ditylenchus dipsaci, Ditylenchus destructor, Pratylenchus neglactus, Pratylenchus penetrans, Paratylenchus goodeyi, Paratylenchus curvitatus and Tylenchorhynchus dubius, Tylenchorhynchus claytoni, Rotylenchus robustus, Heliocotylenchus multicinctus, Radopholus similis, Belonolaimus longicaudatus, Longidorus elongatus, Trichodorus primitivus.

The active ingredient can e.g. in the form of directly sprayable solutions, Powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, Spreading agents, granulates by spraying, misting, dusting, scattering or Pouring can be applied. The forms of application depend entirely on the intended use; In any case, they should have the finest possible distribution of the invention Ensure active ingredient.

For the production of directly sprayable solutions, emulsions, pastes and oil dispersions come mineral oil fractions with a medium to high boiling point, such as kerosene or diesel oil, furthermore coal tar oils etc., as well as oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. benzene, toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, e.g. methanol, ethanol, propanol, butanol, chloroform, carbon tetra-carbon, Cyclohexanol, cyclohexanone, chlorobenzene, isophorone etc., strongly polar solvents, e.g. dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone, water, etc., into consideration.

Aqueous use forms can be made from emulsion concentrations, pastes or wettable powders (wettable powders, image dispersions prepared by adding water will. The active ingredient can be used to produce emulsions, pastes or oil dispersions as such or dissolved in a dl or solvent, by means of wetting, adhesive, dispersing or emulsifiers are homogenized in water. But it can also be made more effective Substance mesh, adhesive, Dispersants or emulsifiers and possibly Solvent or oil existing concentrates are made for dilution with water are suitable.

The following surface-active substances should be mentioned: alkali, alkaline earth, Ammonium salts of lignosulphonic acid, naphthalenesulphonic acids, phenolsulphonic acids, Alkyl aryl sulfonates, alkyl sulfates, alkyl sulfonates, alkali and alkaline earth salts of Dibutylnaphthalenesulfonic acid, lauryl ether sulfate, fatty alcohol sulfates, fatty acid alkali and alkaline earth salts, salts of sulfated hexadecanols, heptadecanols, octadecanols, Salts of sulfated fatty alcohol glycol ether, condensation products of sulfonated Naphthalene and naphthalene derivatives with formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctylphenol octylphenol, nonylphenol, alkylphenol polyglycol ether, Tributylphenyl polyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide octylphenol ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ethers, Tributylphenyl polyglycol ethers, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ether, ethoxylated polyoxypropylene, Lauryl alcohol polyglycol ether acetal, sorbitol esters, lignin, sulphite waste liquors and methyl cellulose.

Powder, grit and dust can be mixed or mixed together Milling the active substance with a solid carrier.

Granules, e.g. coating, impregnation and homogeneous granules, can be prepared by binding the active ingredient to solid carriers. Festivals Carriers are e.g. mineral earths such as silica gel, silicas, silica gels, silicates, Talc, kaolin, attaclay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, Calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers, such as ammonium sulfate, Ammonium phosphate, ammonium nitrate, ureas and vegetable products such as cereal flour, tree bark, wood and nutshell flour, Cellulose powder and other solid carriers.

The formulations contain between 0.1 and 95 percent by weight of active ingredient, preferably between 0.5 and 90 percent by weight.

The active ingredient concentrations in the ready-to-use preparations can be varied in larger areas. In general, they are between 0.0001 and 100%, preferably between 0.01 and 10%.

The active ingredient can also be used with good success in the ultra-low-volume procedure can be used so that it is possible to use formulations up to 95% or even the Apply 100% active ingredient alone.

The preparations are used in amounts of 1 to 100 kg of active ingredient per ha evenly applied and then worked into the soil.

Various types of oils, herbicides, fungicides, Insecticides, bactericides, possibly also immediately before use (Tank mix), can be added. These agents can be compared to the agents according to the invention in Weight ratio 1:10 to 10: 1 are added.

For example, the following compounds can be added: 1, 2-dibromo-3-chloropropane 1,3-dichloropropene 1,3-dichloropropene + 1 1,2-dichloropropane 1,2-dibromoethane 2-sec-butyl-phenyl-N-methylcarbamate oCh lorpheny l-N-methyl carb amate 3-isopropyl-5-methyl-phenyl-N-methylcarbamate o-isopropoxyphenyl-N-methylcarbamate 3,5-dimethyl-4-methylmercapto-phenyl-N-methylcarbamate 4-dimethylamino-3,5-xylyl-N-methylcarbamate 2- (1,3-Dioxolan-2-yl) -phenyl-N-methylcarbamate 1-naphthyl-N-methylcarbamate 2,3-dihydro-2,2-dimethyl-benzofuran-7-yl-N-methylcarbamate 2,2-Dimethyl-1,3-benzodioxol-4-yl-N-methylcarbamate, 2-dimethylamino-5,6-dimethyl-4-pyrimidinyl-dimethylcarbamate 2-methyl-2- (methylthio) propionaldehyde-O- (methylcarbamoyl) -oxime S-methyl-N- [(methylcarbamoyl) ox -thio-acetimidate methyl-N ', N'-dimethyl-N [(methylcarbamoyl) oxy] -1-thiooxamidate N- (2-methyl-4-chlorophenyl) -N', N'-dimethylformamidine Tetrachlorothiophene O, O-Dimethyl O- (p-nitrophenyl) phosphorothioate O, O-diethyl O- (p-nitrophenyl) phosphorothioate O-ethyl-O- (p-nitrophenyl) -phenyl-phosphonothioate 0,0-dimethyl-0- (3-methyl-4-nitrophenyl) -phosphorothioate O, O-diethyl O- (2,4-dichlorophenyl) -phosphorothioate O-ethyl-0- (2,4-dichlorophenyl) -phenyl-phosphonothioate 0,0-dimethyl-0- (2,4,5-trichlorophenyl) -phosphorothioate 0-ethyl-0- (2,4,5-trichlorophenyl) -ethyl-phosphonothioate O, O-dimethyl-O- (4-bromo-2,5-dichlorophenyl) -phosphorothioate 0,0-dimethyl-0- (2,5-dichloro-4-iodophenyl) -phosphorothioate 0,0-Dimethyl-0- (3-methyl-4-methylthiophenyl) phosphorothioate O-Ethyl-O- (3-methyl-4-methylthiophenyl) -isopropyl-phosphoramidate O, O-diethyl-O- [p- (methylsulfinyl) phenyl] -phosphorothioate, O-ethyl-S-phenyl-ethyl-phosphonodithioate 0.0 diethyl 2-chloro-1- (2,4-dichlorophenyl) -vinyQ -phosphate O, O-dimethyl-L2-chloro-1- (2,4,5-trichlorophenyl) g vinyl phosphate O, O-dimethyl-S- (1-phenyl) -ethyl acetate-phosphorodithioate bis- (dimethylamino) -fluorophosphine oxide Octamethyl-pyrophosphoramide O, O, O, O-tetraethyl-dithio-pyrophosphate, S-chloromethyl-O, O-diethyl-phosphorodithioate O-ethyl-S, S-dipropyl-phosphorodithioate 0,0-dimethyl-0-2,2-dichlorovinyl phosphate 0,0-dimethyl-1,2-dibromo-2,2-dichloroethyl-phosphate O, O-dimethyl-2,2,2-trichloro-1-hydroxy-ethyl-phosphonate O, O-dimethyl-S- [1,2-biscarbethoxy-ethyl- (1)] -phosphoridithioate 0,0-Dimethyl-O- (1-methyl-2-carbmethoxy-vinyl) -phosphate O, O-dimethyl-S- (N-methyl-carbamoyl-methyl) -phosphorodithioate O, O-Dimethyl-S- (N-methyl-carbamoyl-methyl) -phosphorothioate O, O-dimethyl-S- (N-methoxyethyl-carbamoyl-methyl) -phosphorodithioate O, O-Dimethyl-S- (N-formyl-N-methyl-carbamoylmethyl) -phosphorodithioate O, O-dimethyl-O- [1-methyl-2- (methyl-carbamoyl) -vinyl] -phosphate O, O-Dimethyl-O- 2 [(1-methyl-2-dimethylcarbamoyl) vinyl] phosphate O, O-dimethyl-O - [(1-methyl-2-chloro-2-diethylcarbamoyl) vinyl] -phosphate O, O-diethyl-S- (ethylthio-methyl) -phosphorodithioate O, O-diethyl-S-Cp-chlorophenylthio) -methyl0-phosphorodithioate 0, Q-Dimethyl-S- (2-ethylthioethyl) -phosphorothioate 0,0-Dimethyl-S- (2-ethylthioethyl) -phosphorodithioate O, O-dimethyl-S- (2-ethylsulphinyl-ethyl) -phosphorothioate 0,0-diethyl-S- (2-ethylthio-ethyl) -phosphorodithioate O, O-Dimethyl-S- (2-ethylsulphinyl-ethyl) -phosphorothioate, O, O-diethyl-thiophosphoryl-iminophenyl-acetonitrile 0,0-diethyl-S- (2-chloro-1-phthalimidoethyl) -phosphorodithioate O, O-diethyl-S - [(6-chloro-benzoxazolon- (2) -yl (3)] -methyldithiophosphate O, O-Dimethyl-S- [-methoxy-t34-thiodiazol-5-onyl (4) -methyg -phosphorodithioate O, O-diethyl-O- [3,5,6-trichloropyridyl- (2)] - phosphorothioate O, O-diethyl-O- (2-pyrazinyl) -phosphorothioate O, O-diethyl-O- [2-isopropyl-4-methyl-pyrimidinyl (6)] -phosphorothioate O, O-diethyl-O- [2- (diethylamino) -6-methyl-4-pyrimidinyl] thionophosphate 0,0-dimethyl-S- (4-oxo-1,2,3-benzotriazin-3-yl- methyl) phosphorodithioate O, O-Dimethyl-S-24,6-diamino-1,3,5-triazin-2-yl) -methyg -phosphorodithioate 0,0-diethyl- (1-phenyl-1,24-triazol-3-yl ) thionophosphate O, S-dimethyl-phosphorus-amido-thioate O, S-dimethyl-N-acetyl-phosphoramidothioate r, -hexachlorocyclohexane 1,1-di- (p-methoxyphenyl) -2,2,2-trichloroethane 6,7,8,9,10,10-hexachloro-1,5,5a, 6,9,9a-hexahydro-6 , 9-methano-2,4,3-benzodioxa-thiephine-3-oxide.

The following examples explain the production and use of the new active ingredient and the production of nematicides, the naphth [2,1-d] isothiazole contained as an active ingredient.

Example 1 In a tantalum autoclave, 95 parts by weight of 1-chloro-2-formylnaphthalene, 16 parts by weight of sulfur and 250 parts by weight of ammonia in 500 parts by weight of methanol Heated to 90 ° C for 20 hours. After the solvent has been distilled off, the The reaction mixture is washed with water, dried and distilled under vacuum. 68.5 parts by weight of aphth 2,1-d isothiazole, melting point = 520 ° C., yield 74% are obtained Theory.

Example 2 Effect on root knot nematodes (Meloidogyne incognita) Young tomato plants are planted in 500 g compost soil each, those heavily with root-knot nematodes is infected.

After three days, the treatment with an aqueous active ingredient preparation takes place by watering the plants with 30 ml of the preparation.

After 6 to 8 weeks, the roots are rated for gall formation.

It turns out that when using an active ingredient preparation of 0.1 wt. Naphthp2,1-diisothiazole no more gall formation occurs.

Example 3 Effect on root knot nematodes (Meloidogyne incognita) Compost soil, which is heavily contaminated with nematodes, is prepared with active ingredients mixed thoroughly so that a final concentration of 10 or 25 ppm active ingredient is obtained.

After 10 days of storage in the greenhouse, each 500 g of soil is filled into flower pots and plant them with young tomato plants or cover them with cucumber seeds (2 per pot). After 8 or 6 weeks, the roots of the plants are examined: When using the preparation containing 10 ppm of active ingredient occasionally occur Gallen, while using the preparation containing 25 psm of active ingredient no gall formation is observed.

Example 4 Effect on root knot nematodes (Meloidogyne incognita) Tomato plants that have been grown in sterilized soil are immersed with the Roots for an hour in an aqueous active ingredient preparation and plant them on it in soil infected with root-knot nematodes.

After 6 to 8 weeks the roots show compared to the control no gall formation when using a 0.1 percent by weight active ingredient preparation.

Example 5 Effect on beet nematodes (Heterodera schachtii) Strong Soil infected with beet nematodes is carefully mixed with the active ingredients and then filled into 4-chamber vessels made of transparent plastic. Every vessel is covered with 4 seeds from the "Diamant" oilseed rape. The volume of the vessels is 200 cm3.

The comparison agent is 2,3-dihydro-2,2-dimethyl-benzofuran-7-yl-N-methylcarbamate. After 8 weeks, the roots of the plants are examined for nematode cysts.

Active substance active substance mene evaluation in the earth naphth [2,1-d] isothiazole 25 ppm no cysts comparison means 100 ppm no cysts 50 ppm isolated cysts 25 ppm numerous cysts. Example 6 Effect on saprophytic soil nematodes 500 g compost soil are mixed intimately with the active ingredient and then placed in pots for 10 days stored moist.

Samples of 100 g of soil are then taken and filled into gauze bags and places them in funnels, the outlet of which is closed with a hose and a pinch valve is. The funnel is carefully filled with water so that the bag is completely covered is. After 24 hours, approx. 2 ml of water are withdrawn from the pinch valve and examined it for the presence of nematodes. At an active ingredient concentration of 100 ppm Naphth p2,1-dgisothiazole no surviving nematodes are found in the soil.

Claims (1)

Claims 1. NaphthL2, i-djisothiazole of the formula 2. Nematicide containing naphth [2,1-d] isothiazole as an active ingredient. 3. Use of naphth [2,1-d] isothiazole as a nematicide. 4. A method for combating nematodes, characterized in that that the soil in which nematodes live with a nematicide according to claim 2 treated.