HU184696B - Pesticides comprising 1,2,3-triazolecarboxylic acid amide derivatives and process for producing 1,2,3-triazolecarboxylic acid amid derivatives - Google Patents

Abstract

The present invention relates to a pesticide having a 1,2,3-triazole carboxamide of formula (I) wherein R1 is alkyl, alkenyl, alkynyl or phenylalkyl; R2 is hydrogen or alkyl; R3 is hydrogen, alkyl, haloalkyl or alkenyl; R 1 is alkyl, alkenyl, cycloalkyl, haloalkyl, phenylalkyl, phenyl substituted with alkyl; or R 3 and together with the nitrogen atom represent a pyrrolidino, piperidino, hexahydroazepino or morpholino group and n is 0, 1 or 2 - together with a liquid and / or solid carrier and optionally a surfactant. The invention also relates to the preparation of 1,2,3-triazole carboxamide derivatives. -1-

Description

The present invention relates to new pesticides containing 1,2,3-triazole carboxylic acid amide derivatives, in particular to herbicides, insecticides, acaricides, fungicides and / or nematocides, and to novel 1,2,3-triazolecarboxylic acid amide derivatives.

Agents containing 1,2,4-triazole derivatives having herbicidal activity are known (U.S. Patent No. 3,952,001). Among these, its action against grasses is distinguished by an agent containing N-ethyl-N-propyl-3- (propylsulfonyl) -1H-1,2,4-triazole-1-carboxamide, which has the advantage, however, that our crops such as maize and cotton, they don't withstand enough.

Agents containing 1,2,3-triazole derivatives having said effect, and the possible applications resulting from them have not been known so far. 15

SUMMARY OF THE INVENTION It is an object of the present invention to provide a novel triazole derivative and a process for the preparation of a novel triazole derivative which provides a wide range of applications, particularly in the field of plant protection. 20

SUMMARY OF THE INVENTION The object of the present invention is to provide an agent which is characterized in that it contains at least one 1,2,3-triazole carboxylic acid amide derivative of formula (I), an isomer or mixture of isomers thereof, in a compound of formula (I).

R 1 is C 1 -C 8 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, or phenyl (C 1 -C 3 alkyl);

R ₂ is hydrogen or C 1-4 alkyl; 30

R ₃ is hydrogen, C 1 -C 10 alkyl, halo-C 4 alkyl, or C 2 -C 6 alkenyl;

R 4 is C 1 -C 10 alkyl, C 2 -C 6 alkenyl, C 4 -C 6 cycloalkyl, halo (C 1 -C 4 alkyl), phenyl (C 1 -C 3) alkyl, or optionally —Phenyl substituted singly with C4 alkyl; or

R ₃ and R 4 together with the nitrogen atom represent a pyrrolidino, 40 piperidino, hexahydroazepino or morpholino group and n is 0, 1 or 2.

Agents containing the compounds of the present invention have the broadest biocidal activity, but are particularly distinguished by their herbicidal, insecticidal, acaricidal, fungicidal and / or nematocidal activity, leading to various applications in the field of plant protection.

Depending upon the particular meaning of the substituents in general terms but each pin ⁵⁰ compounds in compositions according to the invention (I) the major fields of use, with which the products containing these compounds exhibit an excellent effect. Thus, they can be used as selective herbicides, plant growth regulators, insecticides, acaricides, fungicides or nematocides.

Thus, in particular, the compounds according to the invention are characterized by their herbicidal activity which in the compound of formula I is R, a C 1-8 alkyl group such as methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, isobutyl, pentyl or isopentyl or phenyl (C 1-3) alkyl such as benzyl, R ₂ is hydrogen, methyl, ⁶⁵ 2 ethyl, propyl, isopropyl, butyl or tert-butyl, R ₃ is up to C 6 -alkyl or alkenyl or chloro-substituted alkyl having up to 4 carbon atoms, for example 5 methyl, ethyl, 2-chloroethyl, propyl, isopropyl, 3-chloropropyl, butyl, sec-butyl, isobutyl , a pentyl group, an isopentyl group, a hexyl group, an allyl group, a 2-methylallyl group, and the radical R yl or alkenyl, optionally substituted with up to 4 carbon atoms, such as methyl, ethyl, 2-chloroethyl, propyl, isopropyl, 3-chloropropyl, butyl, sec-butyl, isobutyl, pentyl; , isopentyl, hexyl, allyl, 2-methylallyl or C4-6cycloalkyl such as cyclohexyl, phenyl (C1-3) alkyl such as benzyl or optionally methyl substituted phenyl such as 4-methylphenyl or R ₃ and R together with the nitrogen atom form a morpholino group, a piperidino group, a pyrrolidino group or a hexamethyleneimino group, and n is 2.

The agents of the invention containing said compounds have the advantage over the known agents that, in addition to their excellent activity against monocotyledonous and some dicotyledonous weeds, they also have a broad selectivity spectrum against crop plants. In addition, they have a high soil herbicidal effect and can be used to control monocotyledonous and dicotyledonous weeds before and after emergence.

The agents of the present invention include Avena fetua, Alopecurus myosuroides, Echinochloa crus galli, Digitaria sanguinalis, Cyperus esculentus, Sorghum halepense, Poa annua, Stellaria media, Senecio vulgaris, Amaranthus retroflexus, Polygonum lapathiofolium and other weeds.

Usually 0.6 to 5 kg of active ingredient / ha are used to control weeds, in which case the agents containing said active compounds are selective in crop crops such as maize, cotton, potato, soybean, pea and bean crops.

Agents containing the above mentioned active compounds as well as other compounds of the formula I also have growth regulating properties.

Visually visible morphological changes are always related to changes in the physiological and biochemical processes in the plant. By way of example, the following changes in plant development caused by the agents of the invention are mentioned:

inhibition of vertical growth, inhibition of root development, intensification of the formation of plant dyes, induction and promotion of foliage ejection.

The agents according to the invention may contain other active substances besides one or more compounds of the formula I. Other pesticides or pesticides may be added depending on the desired purpose.

If the spectrum of action is to be broadened, other herbicides may be added to the agents of the invention. Examples include triazine derivatives, aminothiazole derivatives, anilide derivatives, diazine derivatives, uracil derivatives, aliphatic carboxylic acid derivatives and halocarboxylic acid derivatives, substituted benzoic acid derivatives, and

184,696 Aryloxycarboxylic acid derivatives, hydrazide derivatives, amide derivatives, nitrile derivatives and ester derivatives thereof, carbamic acid and thiocarbamic acid derivatives, urea derivatives, 1,3,6-trichloro _benzyloxy-5 rodántartal- propanil and instrumentation may be mentioned as herbicides as mixture partners.

Other additives include, for example, non-phytotoxic additives which result in a large increase in the activity of herbicides such as wetting agents, emulsifiers, solvents and oily additives.

Are distinguished by an insecticidal and / or acaricidal activity, in particular, agents of formula (I) compounds of the general formula R is methyl, ethyl, propücsoport, allyl, propyn-2-yl, R ₂ represents a ₁₅ hydrogen atom, methyl, ethyl, propyl , butyl or tert-butyl, R ₃ is hydrogen or methyl, and R 4 is methyl and n is 0.

Agents containing these compounds have significant insecticidal and / or acaricidal activity. A special advantage is that they have a great initial effect.

Agents containing the compounds of the invention can be used to control many economically significant pests, especially those of the order of Dipteras, Coleopteras, Rhynchots and Orthopteras.

Agents containing the compounds in question have a very good effect, with a concentration of 0.5 to less than 0.01% of the active ingredient being used in practice. 3θ

Among the agents containing the compounds of the invention, the agent containing 4-methyl-5-methylthio-1,2,3-triazole-1 (2,3) -carboxylic acid dimethylamide occupies an outstanding position.

These agents of the present invention may also contain other active compounds other than 35 or more compounds of formula (I). Depending on the intended purpose, other plant protection products and adjuvants such as solvents, wetting agents and oils may be added. 40

In particular, agents having a compound of formula (I) in which R 1 is a C 1-8 alkyl group or an alkenyl group of up to 6 carbon atoms, such as methyl, ethyl, propyl, isopropyl, butyl, have non-nematocidal activity. , a sec-butyl group, an isobutyl group, a t-butyl group, a pentyl group, an isopentyl group or an allyl group, a 2-methylallyl group or a phenyl (C 1-3 alkyl) group such as benzyl, the substituent R ₂ being hydrogen. , methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, isobutyl or tert-butyl group, R _s is hydrogen, up to 6 carbon atoms, alkyl or alkenyl, or, for example, methyl, ethyl, pro- 55 pilcsoport , isopropyl, butyl, sec-butyl, tert-butyl, allyl, R he is an alkyl or alkenyl group containing up to 6 carbon atoms, such as methyl, ethyl, propyl, sec-butyl, isobutyl, tert-butyl, allyl and n is 0.

Agents containing these compounds are surprisingly non-phytotoxic at practical application rates, so that negative influence on plant growth is excluded.

Preferably, the agents of the present invention are applied uniformly to the soil at a rate of 10 to 50 kg of active ingredient per hectare for application to nematodes and then applied to the soil.

Examples of phytopathogenic nematodes which can be controlled by the agent of the present invention include: migratory root nematodes of the genera Tyienchorhynchus, Pratylenchus, Paratylenchus, Heliocotylenchus, Xiphinema, Trichodorus and Longidorus; root nematodes such as Meloidogyne incognita, Meloidogyne hapla, Meloidogyne arenaria; cyst-forming root nematodes such as Globodera rostochiensis and Heterodera schachtii.

For this purpose, the agents according to the invention may be used alone or in the form of preparations thereof, such as ready-to-use solutions, emulsifiable concentrates, emulsions, suspensions, sprayable powders, pastes and granules. Usage is by conventional means such as irrigation, spraying, gasification, smoking, spraying or spraying.

Finally, all of the compounds of formula (I) exhibit a fungicidal action, both in the treatment of plants and in the application to plants seeds. The agents of the present invention provide an extraordinary contribution to the technical progress by providing a solution in cases where a known fungicide is no longer effective (due to fungal resistance) or is no longer applicable.

The agents of the present invention are formulations, such as powders, sprays, granules, solutions, emulsions or suspensions, which contain one or more compounds of Formula I, liquid and / or solid carriers or diluents, and optionally wetting, tackifying, emulsifying or emulsifying agents. and / or dispersing aids.

Suitable liquid carriers include, by way of example, water, aliphatic and aromatic hydrocarbons such as benzene, toluene, xylene, cyclohexanone, isophorone, dimethylsulfoxide, dimethylformamide, and mineral oil fractions.

Solid carriers include mineral soils such as tonsil, silica gel, talc, kaolin, Attaclay, limestone, silica and plant products such as flour.

Examples of surfactants include calcium lignin sulfonate, polyoxyethylene alkylphenyl ether, naphthalenesulfonic acids and their salts, formaldehyde condensates, fatty alcohol sulfates, and substituted benzenesulfonic acids and their salts.

If the agents of the present invention are used for seed dressing, then dyes may also be added thereto so that the seed dressed has a clearly visible color.

The active ingredient content of the various formulations may vary widely. For example, the agents of the present invention will contain from about 10% to about 80% by weight of the active ingredient, from about 90% to about 20% by weight of liquid and / or solid carriers and optionally up to about 20% by weight of surfactant.

The agents of the invention may be applied in the conventional manner, for example, with water as the vehicle, using about 100-1000 liters of spray liquid per hectare. THE

The agents of the invention can be used in the so-called "Low-Volume" or "Ultra-Low-Volume" process as well as in the form of so-called micro-granules.

Compounds of formula (I) wherein

R 1 is C 1 -C 8 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, or phenyl (C 1 -C 3 alkyl);

R ₂ is hydrogen or C 1-8 alkyl;

R ₃ is hydrogen, C 1 -C 10 alkyl, halo-C 1 -C 4 alkyl, or C 2 -C 6 alkenyl;

R 1 is C 1 -C 10 alkyl, C 2 -C 6 alkenyl, C 3 -C 8 cycloalkyl, halo (C 1 -C 4) alkyl, phenyl (C 1 -C 3) alkyl, or optionally halogen, or Phenyl monosubstituted with C 1-4 alkyl;

R ₃ and R ₄ together represent a C 3 -C 6 alkylene chain optionally interrupted by an oxygen atom and n is 0, 1 or 2 - for example, by the formula: 3-triazole derivative of an acid binding agent in the presence of a carbamoyl halide of formula (H), and optionally a catalyst, preferably an organic base, for example, reacted with triethylamine in the presence of a generic video (TV) ₃₀ Letum isocyanate to (Π) ( ΠΙ) and (TV) R ₁ , R ₂ , R ₃ , R ₄ and n are as defined above and

X is halogen, preferably chlorine.

The reaction is carried out at 0 to 120 ° C, but usually at room temperature. Reagents are used in the synthesis of the compounds of the invention in approximately equimolar amounts. Polar organic solvents may be used as the reaction medium. Solvents and suspending agents are selected depending on the carbamoyl halides used, the acid acceptors used, and the appropriate isocyanates. Examples of solvents and suspending agents include acid nitriles such as acetonitrile, ethers such as tetrahydrofuran and dioxane, acid amides such as dimethylformamide, ketones such as acetone and chlorinated hydrocarbons such as chloroform and carbon tetrachloride.

As the acid acceptor, organic bases such as triethylamine, Ν, Ν-dimethylamine and pyridine may be used, or inorganic bases such as the oxides, hydroxides and carbonates of the alkali and alkaline earth metals 50. Liquid bases such as pyridine can be used simultaneously as a solvent.

The liquid or solid 1,2,3-triazolecarboxylic acid amide derivatives prepared according to the above process variants can be isolated from the reaction mixture by conventional means, for example by distillation of the solvent used under normal or reduced pressure or by precipitation with water.

Although the compounds 60 of the present invention obtained by these methods are very pure, they may be further purified, for example by recrystallization or chromatography.

The 1,2,3-triazoles of the general formula (H) can be prepared by alkylating the corresponding 4-mercaptotriazoles and optionally oxidizing them in a known manner.

Preparation of starting materials

A. Alkylthio-1,2,3-triazoles

4-Methyl-5- (methylthio) -1,2,3-triazole (Compound IX)

To a solution of 13.8 g (0.12 mol) of 5-mercapto-4-methyl-1,2,3-triazole in 60 ml of methanol was added dropwise 4.79 g (0.12 mol) of sodium hydroxide in 20 ml of ethanol at room temperature.

It is then stirred at 30 ° C with 19.85 g (0.14 mol) of methyl iodide and, after standing at room temperature overnight, is concentrated in vacuo at 40 ° C.

The residue is mixed with 150 ml of water and extracted with ether. The organic phase was dried over magnesium sulfate, filtered and evaporated. The remaining crystals were recrystallized from cyclohexane.

Yield 14.6 g = 94.3% of theory. Melting point: 71-71.5 ° C. C ₄ H ₇ N ₃ S Molecular weight: 129.19. The following starting materials can be prepared analogously: The name of the compound Physical constant 4- (methylthio) -l, 2,3-triazole Melting point: 47 ° C 4- (ethylthio) -l, 2,3-triazole n * °: 1.5449 4- (propylthio) -l, 2,3-triazole *: 1.5375 4- (Isopropyl-thio) -l, 2,3-triazole n * °: 1.5331 4- (butylthio) -l, 2,3-triazole n * °: 1.5280 4- (l-methyl-propylthio) -l, 2,3- triazole n * °: 1.5281 4- (Allylthio) -1,2,3-triazole n '°: 1.5561 4- (Isobutyl-ylthio) -l, 2,3-triazole n * °: 1.5244 4- (2-propynylthio) -l, 2,3-triazole semi-crystalline 4- (Benzylthio) -1,2,3-triazole Mp 61.5-63.5 ° C

B. Alkylsulfmyl-1,2,3-triazoles

4- (Methylsulfinyl) -1,2,3-triazole (Compound X)

A solution of 4- (methylthio) -1,2,3-triazole (57.5 g, 0.5 mol) in acetic acid (200 ml) was added in 10 minutes to 30% hydrogen peroxide (61.1 ml, 0.6 mol). ice.

The reaction mixture was stirred for 30 minutes at 40-45 ° C. After standing overnight, it was heated at 80 ° C for 30 minutes, cooled to room temperature, and the dark red reaction solution was decolorized with 0.2 g of sodium disulfite. The reaction solution was then concentrated in vacuo at 40 ° C. Digestion of the oily residue with diisopropyl ether initiates crystallization. Yield: 62.3 g = 95% of theory. Melting point: 66-67 ° C.

C ₃ H ₅ N ₃ OS molecular weight: 131.16.

C. Alkylsulfonyl-1,2,3-triazoles

4- (Propylsulfonyl) -1,2,3-triazole (Compound XI)

Of a solution of 103.2 g (0.72 mol) of 4- (propylthio) -1,2,3-triazole in 320 ml of acetic acid and 420 ml of water in portions at 45-55 ° C over a period of 30 minutes. g (1.08 mol) of potassium permanganate are added. The reaction mixture was stirred at 45 ° C for 10 min and a solution of 159.8 g (0.84 mol) of sodium disulfite in 500 ml of water was added at 20 ° C until complete coloration. It is then extracted with 250-250 in. Of ethyl acetate 4 times. The organic phase is dried over magnesium sulfate, filtered and concentrated in vacuo.

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Yield: 119 g = 94.5% of theory. n ²⁰ : 1.5085

C ₅ H ₉ N ₃ O ₂ S molecular weight: 175.21.

The following starting materials can be prepared analogously:

The name of the compound Physical constant 4- (methylsulfonyl) -l, 2,3-triazole 101-103 ° C 4- (isopropylsulfonyl) -l, 2,3- triazole n ²⁰ ; 1.5067 4- (benzyl-sulfonyl) -l, 2,3-triazole M.p. 163-166 ° C 4- (ethylsulfonyl) -l, 2,3-triazole Melting point: 46-48 ° C 4- (butyl-sulfonyl) -l, 2,3-triazole n ²⁰ : 1.4948 4- (l-methyl-propylsulfonyl) - -1,2,3-triazole n ²⁰ : 1.4858 4- (Isobutyl-sulfonyl) -l, 2,3- triazole M.p. 71-73 ° C

The following Examples further illustrate the preparation of the 1,2,3-triazole carboxylic acid amide derivatives of the present invention.

Example 1

4- (Propylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid dipropylamide (Compound 1)

A solution of 4- (propylsulfonyl) -1,2,3-triazole (8.75 g, 0.05 mol) in acetonitrile (25 mL) was stirred at room temperature with triethylamine (5.55 g, 0.055 mol). Under stirring at 70 ° C, 8.18 g (0.05 mol) of dipropylcarbamoyl chloride are added dropwise over 10 minutes. The reaction mixture was stirred for 2 hours at 70 ° C and allowed to stand overnight at ₃ θ. The reaction mixture was concentrated in vacuo at 40 ° C and the residue was mixed with 100 ml of ice water and extracted with ether. The organic layer was washed with 1% sodium bicarbonate solution, dried over magnesium sulfate, filtered and evaporated. 35

Yield: 12.6 g = 83.4% of theory. n ²⁰ ; 1.4964.

The product obtained is probably a mixture of isomers of N ¹ - and N ² -carbamoylated products.

Example 2 ₄₀

4-Methyl-5- (methylthio) -1,2,3-triazole-1 (2,3) -carboxylic acid dimethylamide [2. and és)]

A solution of 16.4 g (0.127 mol) of 4-methyl-5- (methylthio) -1,2,3-triazole in 160 ml of tetrahydrofuran was stirred at room temperature with 15.35 g (0.152 mol) of triethyl 45 amine. Then, while stirring at 50 ° C, dimethylcarbamoyl chloride (16.3 g, 0.152 mol) was added dropwise to the reaction mixture over 5 minutes. Subsequently, stirring was continued for 4 hours at 50 ° C and allowed to stand at room temperature for 1 day. It is then concentrated in vacuo at 40 [deg.] C., the residue is mixed with 150 ml of water and extracted twice with 75 ml of 75 ml of chloroform. The organic layer was washed with 1% sodium bicarbonate solution, dried over magnesium sulfate, filtered and evaporated. Yield: 23.5 g = 92.5% of theory. 55 n ²⁰ : 1.5370.

A uniform isomer is obtained, probably an N ² -carbamoylated product.

Example 3

4- (Methylthio) -1,2,3-triazole-1 (2,3) -carboxylic acid methylamide 60 [3. (ΧΙΠ)]

11.5 g (0.1 mol) of 4- (methylthio) -1,2,3-triazole are dissolved in 100 ml of tetrahydrofuran and the solution is stirred at 5 ° C for 3 minutes to 6.27 g (0.11 mol) methyl isocyanate and then 0.1 ml of triethylamine as catalyst. Stir at 65 ° C for 1 hour and then at room temperature for 1 1/2 hours. The reaction mixture was concentrated in vacuo at 40 ° C and the resulting residue (mixture of isomers) was recrystallized from 500 ml of water with vigorous stirring.

Yield: 8.7 g = 50.5% of theory. Melting point: 107-109 ° C (dec.).

A uniform isomer is obtained, probably an N ² -carbamoylated product.

Example 4

4- (Methylthio) -1,2,3-triazol-1 (2,3) -carboxylic acid methylamide [4. (ΧΠΙ)]

11.5 g (0.1 mol) of 4- (methylthio) -1,2,3-triazole are dissolved in 125 ml of carbon tetrachloride and this solution is stirred at room temperature for 10 minutes with 6.27 g (0.11 mol) metilizocianáttal. After standing overnight, the crystals are filtered off with suction and washed with a little carbon tetrachloride. The crystals were recrystallized from a mixture of benzene and cyclohexane. Yield: 12.2 g = 70.9% of theory. Melting point: 109-110 ° C (dec.).

A uniform isomer is obtained, probably an N'-carbamoylated product.

The following compounds of the invention may be prepared analogously:

compound sign The name of the compound Physical constant 5 4- (Methylthio) -1,2,3-triazole- l (2,3) -carboxylic acid methylamide (Isomer mixture) 93 ° C (dec.) 6 4- (methylthio) -l, 2,3-triazole l (2,3) -carboxylic acid anilide (Isomer mixture) 86.5-89 'C (dec.) 7 4- (methylthio) -l, 2,3-triazole l (2,3) -carboxylic acid ethylamide (Isomer mixture) semi-crystalline 8 4- (Methylthio) -1,2,3-triazole-1 (2,3) -carboxylic acid propylamide (mixture of isomers) n ": 1.5482 9 4- (Methylthio) -1,2,3-triazole-1 (2,3) -carboxylic acid butylamide (mixture of isomers) n ": 1.5400 10 4- (methylthio) -l, 2,3-triazole l (2,3) -carboxylic acid cyclohexylmethyl-amide (Isomer mixture) M.p. 63-71 ° C 11 4- (methylthio) -l, 2,3-triazole l (2,3) -carboxylic acid anilide (N-isomer) 98-100 ° C 12 4- (Methylthio) -1,2,3-triazole-1 (2,3) -carboxylic acid anilide (N ² isomer) M.p. 93-95 ° C 13 4- (Methylthio) -1,2,3-triazole-1 (2,3) -carboxylic acid (2-methylanilide) (N ² -isomer) Mp 80-88 ° C 14 4- (Methylthio) -1,2,3-triazole-1 (2,3) -carboxylic acid (2-chloroanilide) (N ² -isomer) Mp 110 'C (dec.) 15 4- (methylthio) -l, 2,3-triazole l (2,3) -carboxylic acid (3-methyl-anilide) (N-isomer) M.p. 91-92.5 'C (dec.) 16 4- (methylthio) -l, 2,3-triazole -1 (2,3) -Carboxylic acid (4-methylanilide) (N-isomer) op .: 108.5-109.5 ° C . 17 4- (Methylthio) -1,2,3-triazole l (2,3) -carboxylic acid (3-chloro-anilide) (N-isomer) 106-107 C 18 4- (Methylthio) -1,2,3-triazole-1 (2,3) -carboxylic acid (4-chloroanilide) (N'-isomer) 109-110 ° C

184,696

compound sign The name of the compound Physical constant Compound sign The name of the compound Physical constant 19 4- (methylthio) -l, 2,3-triazole l (2,3) -carboxylic acid allyl amide (N-isomer) Mp 50-55 ° C 5 41 4- (methylsulfonyl) -l, 2,3-triazole l (2,3) -carboxylic acid ethylamide (Isomer mixture) Mp 110-1U 'C 20 4- (methylthio) -l, 2,3-triazole l (2,3) -carboxylic acid dimethylamide (Isomer mixture) n ": 1.5569 42 4- (methylsulfonyl) -l, 2,3-triazole l (2,3) -carboxylic acid propylamide (Isomer mixture) Mp: 66-72 'C 21 4- (ethylthio) -l, 2,3-triazole l (2,3) -carboxylic acid methylamide (Isomer mixture) n ": 1.5571 10 43 4- (methylsulfonyl) -l, 2,3-triazole l (2,3) -carboxylic acid butylamide (Isomer mixture) M.p. 70-72 ° C 22 4- (propylthio) -l, 2,3-triazole l (2,3) -carboxylic acid methylamide (Isomer mixture) Mp: 35-38 ° C 44 4- (methylsulfinyl) -l, 2,3-triazole l (2,3) -carboxylic acid methylamide (Isomer mixture) M.p. 95-97 'C 23 4- (Isopropylthio) -1,2,3-triazole-1 (2,3) -carboxylic acid methylamide (mixture of isomers) n ": 1.5432 15 45 4- (Methylsulfinyl) -1,2,3-triazole-1 (2,3) -carboxylic acid ethylamide (mixture of isomers) n ": 1.5370 24 4- (Butylthio) -1,2,3-triazole-1 (2,3) -carboxylic acid methylamide (mixture of isomers) n ': 1.5408 20 46 4- (Methylsulfinyl) -1,2,3-triazole-1 (2,3) -carboxylic acid propylamide (mixture of isomers) n ': 1.5288 25 4- (l-methyl-propylthio) -l, 2,3-triazole l (2,3) -carboxylic acid methylamide (Isomer mixture) n ": 1.5390 47 4- (Methylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid anilide (mixture of isomers) 134-137 ° C 26 4- (Allyl-thio) -l, 2,3-triazol-l (2,3) - carboxylic acid methylamide (Isomer mixture) semi-crystalline 25 48 4- (methylsulfonyl) -l, 2,3-triazole l (2,3) -carboxylic acid cyclohexylmethyl-amide (Isomer mixture) 96-103 C 27 4- (butylthio) -l, 2,3-triazole l (2,3) -carboxylic acid methylamide (N-isomer) M.p. 75-77 ° C 49 4- (methylsulfonyl) -l, 2,3-triazole l (2,3) -carboxylic acid (4-chloro-anilide) (Isomer mixture) Mp: 170-171 ° C 28 4- (1-Methyl-propyl-thio) -1,2,3-triazole-1 (2,3) -carboxylic acid methylamide (N'-isomer) M.p. 66-69 'C 30 50 4- (methylsulfonyl) -l, 2,3-triazole l (2,3) -carboxylic acid (4-methyl-anilide) (Isomer mixture) 156-158 ° C 29 4- (Allylthio) -1,2,3-triazole-1 (2,3) -carboxylic acid methylamide (N'-isomer) 84-85 ° C 51 4- (methylsulfonyl) -l, 2,3-triazole l (2,3) -carboxylic acid allyl amide (Isomer mixture) M.p. 91-92,5'C 30 4- (Ethylthio) -1,2,3-triazole- l (2,3) -carboxylic acid methylamide (N-isomer) 84.5-86 ° C 35 52 4-Methyl-5- (methylthio) -l, 2,3-triazole l (2,3) -carboxylic acid methylamide (N-isomer) 102-106'C 31 4- (Propylthio) -1,2,3-triazole-1 (2,3) -carboxylic acid methylamide (N'-isomer) M.p. 75-75 ° C 53 4- (methylsulfinyl) -l, 2,3-triazole l (2,3) -carboxylic acid butylamide (Isomer mixture) n ": 1.5128 32 4- (Isopropyl-thio) l, 2,3-triazole l (2,3) -carboxylic acid methylamide (N-isomer) M.p. 91-92.5 ° C 40 54 4- (methylsulfinyl) -l, 2,3-triazole l (2,3) -carboxylic acid (4-methyl-anilide) (Isomer mixture) 122-123 ° C 33 4- (Isobutylthio) -1,2,3-triazole-1 (2,3) -carboxylic acid methylamide (mixture of isomers) n £: 1.5382 55 4- (methylsulfinyl) -l, 2,3-triazole l (2,3) -carboxylic acid (4-chloro-anilide) (Isomer mixture) Mp: 150 'C (dec.) 34 4- (2-propynylthio) -l, 2,3-triazole l (2,3) -carboxylic acid methylamide (Isomer mixture) semi-crystalline 45 56 4- (methylsulfinyl) -l, 2,3-triazole l (2,3) -carboxylic acid allyl amide (Isomer mixture) n ": 1.5365 35 4- (benzylthio) -l, 2,3-triazole l (2,3) -carboxylic acid methylamide (Isomer mixture) 50-54 ° C 50 57 4- (Methylsulfinyl) -1,2,3-triazole-1 (2,3) -carboxylic acid dimethylamide (mixture of isomers) n ": 1.5391 36 4- (Isobutyl-ylthio) -l, 2,3-triazole l (2,3) -carboxylic acid methylamide (N-isomer) M.p. 82-83.5 ° C 58 4- (Methylsulfonyl) -1,2,3-triazole - l (2,3) -carboxylic acid diethylamide (Isomer mixture) n ": 1.5065 37 4- (2-Propynylthio) -1,2,3-triazole-1 (2,3) -carboxylic acid methylamide (N'-isomer) 101-102 'C 55 59 4- (isopropylsulfonyl) -l, 2,3-triazole l (2,3) -carboxylic acid methylamide (Isomer mixture) 141-149 ° C 38 4- (benzylthio) -l, 2,3-triazole l (2,3) -carboxylic acid methylamide (N-isomer) 84-85 ° C 60 4- (Isopropylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid dimethylamide (N'-isomer) 112-113 ° C 39 4- (Methylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid dimethylamide (mixture of isomers) M.p. 73-83 ° C 60 61 4- (isopropylsulfonyl) -l, 2,3-triazole l (2,3) -carboxylic acid dimethylamide (N-isomer) n ™: 1.5061 40 4- (Methylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid methylamide (mixture of isomers) 132-134 'C 62 4- (Isopropylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid diethylamide (mixture of isomers) n ": 1.4909

184,696

Compound sign The name of the compound Physical constant Compound sign The name of the compound Physical constant 63 4- (propylsulfonyl) -l, 2,3-triazole 99-109 ° C 84 4- (l-methyl-propylsulfonyl) -l, 2,3- ng: 1.5019 l (2,3) -carboxylic acid methylamide 5 triazol-l (2,3) -carboxylic acid diethylamide (Isomer mixture) (Isomer mixture) 64 4- (propylsulfonyl) -l, 2,3-triazole ng: 1.5131 85 4- (benzyl-sulfonyl) -l, 2,3-triazole ng: 1.5538 1 (2,3) -carboxylic acid dimethylamide l (2,3) -carboxylic acid dimethylamide (Isomer mixture) (Isomer mixture) 65 4- (propyn-sulfonyl) -l, 2,3-triazole ng: 1.4992 86 4- (ethylthio) -l, 2,3-triazol-l (2,3) - ng: 1.5458 l (2,3) -carboxylic acid diethylamide 10 carboxylic acid dimethylamide (Isomer mixture) (Isomer mixture) 66 4- (propylsulfonyl) -l, 2,3-triazole M.p. 48-60 ° C 87 4- (ethylthio) -l, 2,3-triazol-l (2,3) - ng: 1.5351 1 (2,3) -carboxylic acid ethylamide carboxylic acid diethylamide (Isomer mixture) (Isomer mixture) 67 4- (propylsulfonyl) -l, 2,3-triazole n ": 1.5031 ₁₅ 88 4- (Isobutyl-ylthio) -l, 2,3-triazol-l (2,3) - ng: 1.5210 l (2,3) -carboxylic acid (N-ethyl-N-propyl) carboxylic acid diethylamide -amide (Isomer mixture) (Isomer mixture) 89 4- (1-Methyl-propyl-thio) -1,2,3-triazole- ng: 1.5331 68 4- (methylsulfonyl) -l, 2,3-triazole ng: 1.5081 1 (2,3) -carboxylic acid dimethylamide l (2,3) -carboxylic acid (N-ethyl-N-propyl) (Isomer mixture) -amide 20 90 4- (1-Methyl-propyl-thio) -1,2,3-triazole- ng: 1.5235 (Isomer mixture) l (2,3) -carboxylic acid diethylamide 69 4- (methylsulfonyl) -l, 2,3-triazole ng: 1.5489 (Isomer mixture) 1 (2,3) -carboxylic acid-N-ethyl-anilide 91 4- (benzylthio) -l, 2,3-triazol-l (2,3) - ng: 1.5988 (Isomer mixture) carboxylic acid dimethylamide 70 4- (isopropylsulfonyl) -l, 2,3-triazole ng: 1.5384 25 (Isomer mixture) -1 (2,3) -Carboxylic acid-N-ethyl anilides 92 4- (benzylthio) -l, 2,3-triazol-l (2,3) - ng: 1.5760 (Isomer mixture) carboxylic acid diethylamide 71 4- (propyl-sulfonyl) -l, 2,3-triazole ng: 1.5406 (Isomer mixture) 1 (2,3) -carboxylic acid-N-ethyl-anilide 93 4- (propylsulfonyl) -l, 2,3-triazole M.p. 67-69 ° C 72 4- (Izorpopil-sulfonyl) -l, 2,3-triazole C, 1.5028 1 (2,3) -carboxylic acid propylamide l (2,3) -carboxylic acid (N-ethyl-N-methylpropyl) - Ou (Isomer mixture) -amide 94 4- (propyn-sulfonyl) -l, 2,3-triazole M.p. 76-79 ° C (Isomer mixture) l (2,3) -carboxylic acid butylamide 73 4- (butylthio) -l, 2,3-triazole ng: 1.5439 (Isomer mixture) l (2,3) -carboxylic acid dimethylamide 95 4- (propylsulfonyl) -l, 2,3-triazole M.p. 68-72 ° C (Isomer mixture) 35 1 (2,3) -carboxylic acid diisopropylamide 74 4- (Isobutyl-ylthio) -l, 2,3-triazole ng: 1.5321 (Isomer mixture) 1 (2,3) -carboxylic acid dimethylamide 96 4- (propylsulfonyl) -l, 2,3-triazole ng: 1.4909 (Isomer mixture) l (2,3) -carboxylic acid dibutyl-amide 75 4- (butyl-sulfonyl) -l, 2,3-triazole ng: 1.5119 (Isomer mixture) 1 (2,3) -carboxylic acid dimethylamide DFI 97 4- (propylsulfonyl) -l, 2,3-triazole ng: 1.5305 (Isomer mixture) l (2,3) -carboxylic acid pyrrolidide 76 4- (butyl-sulfonyl) -l, 2,3-triazole ng: 1.5010 (Isomer mixture) 1 (2,3) -carboxylic acid diethylamide 98 4- (propylsulfonyl) -l, 2,3-triazole ng: 1.5270 (Isomer mixture) l (2,3) -carboxylic acid piperidide 77 4- (Isobutylsulfonyl) -1,2,3-triazole ng: 1.5107 (Isomer mixture) l (2,3) -carboxylic acid dimethylamide 45 99 4- (propylsulfonyl) -l, 2,3-triazole ng: 1.5176 (Isomer mixture) 1 (2,3) -carboxylic acid diallylamide 78 4- (Isobutylsulfonyl) -1,2,3-triazole ng: 1.4999 (Isomer mixture) 1 (2,3) -carboxylic acid diethylamide 100 4- (propylsulfonyl) -l, 2,3-triazole ng: 1.5251 (Isomer mixture) l (2,3) -carboxylic acid morpholide 79 4- (ethylsulfonyl) -l, 2,3-triazole M.p .: 79-82 ° C _5Q (Isomer mixture) l (2,3) -carboxylic acid dimethylamide 101 4- (butyl-sulfonyl) -l, 2,3-triazole ng: 1.4990 (Isomer mixture) l (2,3) -carboxylic acid (N-ethyl-N-methylpropyl) - 80 4- (ethylsulfonyl) -l, 2,3-triazole ng: 1.5080 -amide l (2,3) -carboxylic acid diethylamide (Isomer mixture) (Isomer mixture) 102 4- (Isobutyl-sulfonyl) -l, 2,3-triazole ng: 1.4972 81 4- (l-methyl-propylsulfonyl) -l, 2,3- ng: 1.5110 55 1 (2,3) -carboxylic acid (N-ethyl-N-methylpropyl) - triazol-l (2,3) -carboxylic acid dimethyl- -amide -amide (Isomer mixture) (Isomer mixture) 103 4- (l-methyl-propylsulfonyl) - ng: 1.4990 82 4- (Benzylsulfonyl) -l, 2,3-triazole 90-91 ° C l, 2,3-triazol-l (2,3) -carboxylic acid l (2,3) -carboxylic acid diethylamide 60 - (N-ethyl-N-ptopil) -amide (Isomer mixture) (Isomer mixture) 83 4- (butylthio) -l, 2,3-triazol-l (2,3) - ng: 1.5242 104 4- (propylsulfonyl) -l, 2,3-triazole ng: 1.4971 carboxylic acid diethylamide l (2,3) -carboxylic acid (N-ethyl-N-butyl) - (Isomer mixture) -amide

(Isomer mixture)

-Ί1

184,696

Compound sign

The name of the compound

Physical constant

Compound sign

The name of the compound

Physical constant

105

106

107

108

109

110

111

112

113

4- (Propylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid dipentylamide (mixture of isomers)

4- (Propylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid (N-ethyl-N-cyclohexyl) -amide (mixture of isomers)

4- (Propylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid diisopropylamide (mixture of isomers)

4- (Ethylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid (N-ethyl-N-propyl) -amide (mixture of isomers)

4- (Ethylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid dipropylamide (mixture of isomers)

4- (Ethylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid butylamide (mixture of isomers)

4- (Butylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid dipropylamide (mixture of isomers)

4- (Butylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid dibutylamide (mixture of isomers)

4- (1-Methyl-propylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid dibutylamide ng: 1.4880 ng: 1.5161 ng: 1.5010 ng: 1 , 4998

M.p. 60-61 ° C ng: 1.4931 ng: 1.4949 ng: 1.4900 ng: 1.4910

114

115

116

117

118

119 (mixture of isomers)

4- (Isobutylsulfonyl) -1,2,3-triazole- ¹ : 1.4920

-1 (2,3) -Carboxylic acid dipropylamide (mixture of isomers)

4- (Isobutylsulfonyl) -1,2,3-triazolene: 1,4887 -1 (2,3) -carboxylic acid dibutylamide (mixture of isomers)

4- (1-Methyl-propylsulfonyl) -1,2,3-ng: 1,4946

-triazole-1 (2,3) -carboxylic acid dipropylamide (isomeric mixture)

4- (1-Methyl-propylsulfonyl) -1,2,3-ng: 1,4971

-triazole-1 (2,3) -carboxylic acid diisopropylamide (isomeric mixture)

4- (Butylsulfonyl) -1,2,3-triazole-ng: 1.4951

-1 (2,3) -Carboxylic acid (N-ethyl-N-butyl) amide (isomeric mixture)

4- (Isobutylsulfonyl) -1,2,3-triazole-ng: 1.4943

l (2,3) -carboxylic acid (N-ethyl-N-butyl) amide

120

121

122

123 (mixture of isomers)

4- (1-Methyl-propylsulfonyl) - ng: 1.4968

-1,2,3-Triazole-1 (2,3) -carboxylic acid (N-ethyl-N-butyl) -amide (mixture of isomers)

4- (Ethylsulfonyl) -1,2,3-triazole-ng: 1.5160

-1 (2,3) -Carboxylic acid (N-ethyl-N-cyclohexyl) -amide (mixture of isomers)

4- (isopropylsulfonyl) -1,2,3-triazole ng: 1.4950

-1 (2,3) -Carboxylic acid dibutylamide (isomeric mixture)

4- (Isopropylsulfonyl) -1,2,3-triazole m.p. 58-60 ° C

-1 (2,3) -Carboxylic acid dipropylamide (mixture of isomers)

124 4- (Butylsulfonyl) -1,2,3-triazole ng: 1,5111 -1 (2,3) -carboxylic acid (N-ethyl-N-cyclohexyl) amide

125 4- (1-Methylpropylsulfonyl) ng: 1.5100

-1,2,3-Triazole-1 (2,3) -carboxylic acid (N-ethyl-N-cyclohexyl) -amide (mixture of isomers)

126 4- (Propylsulfonyl) -1,2,3-triazolone: 1,5011 -1 (2,3) -carboxylic acid diisobutylamide (isomeric mixture)

127 4- (Propylsulfonyl) -1,2,3-triazolene: 1,4891 -1 (2,3) -carboxylic acid dihexylamide (isomeric mixture)

128 4- (Propylsulfonyl) -1,2,3-triazolyl: 1,5444 -1 (2,3) -carboxylic acid (N-ethyl-N-benzyl) amide (isomeric mixture)

129 4- (Propylsulfonyl) -1,2,3-triazolyl: 1,5055 -1 (2,3) -carboxylic acid (N-ethyl-N-isopropyl) amide (isomeric mixture)

130 4- (Propylsulfonyl) -1,2,3-triazolene: 1,5272 -1 (2,3) -carboxylic acid N, N-hexamethylene amide (isomeric mixture)

131 4- (Propylsulfonyl) -1,2,3-triazole m.p. 124 DEG C. -1 (2,3) -Carboxylic acid N- (2-cyanoethyl) amide (mixture of isomers).

132 4- (Propylsulfonyl) -1,2,3-triazolyl: 1,5509 -1 (2,3) -carboxylic acid N-methylanilide (mixture of isomers)

133 4- (Ethylsulfonyl) -1,2,3-triazole ng: 1,5002 -1 (2,3) -carboxylic acid (N-ethyl-N-butyl) amide (isomeric mixture)

134 Crystals of 4- (isopropylsulfonyl) -1,2,3-triazole-1,2-2,3-triazole-carboxylic acid (N-ethyl-N-butyl) -amide (isomeric mixture)

135 4- (Isobutylsulfonyl) -1,2,3-triazole ng: 1,5078 -1 (2,3) -carboxylic acid (N-ethyl-N-cyclohexyl) amide (isomeric mixture)

136 4- (Butylsulfonyl) -1,2,3-triazole ng: 1,4962 -1 (2,3) -carboxylic acid (N-ethyl-N-isopropyl) amide (isomeric mixture)

137 4- (Isobutylsulfonyl) -1,2,3-triazole ng: 1,4970 -1 (2,3) -carboxylic acid (N-ethyl-Nisotopopyl) amide (isomeric mixture)

138 4- (Propylsulfinyl) -1,2,3-triazolone: 1,5192 -1 (2,3) -carboxylic acid diethylamide (mixture of isomers)

139 4- (Propylsulfonyl) -1,2,3-triazolyl: 1,5238 -1 (2,3) -carboxylic acid bis (2-chloroethyl) amide (isomeric mixture)

140 4- (Butylsulfonyl) -1,2,3-triazole ng: 1,5429 -1 (2,3) -carboxylic acid (N-ethyl-N-benzyl) amide (isomeric mixture)

141 4- (1-Methyl-propylsulfonyl) -1,2,3-ng: 1,5392-triazole-1 (2,3) -carboxylic acid (N-ethyl-N-benzyl) -amide (isomeric mixture)

184,696 compound mark

The name of the compound

Physical constant

142

143

144

145

146

147

148

149

150

4- (Isobutyl-sulfonyl) -l, 2,3-triazole l (2,3) -carboxylic acid (N-ethyl-N-benzyl) - -amide (Isomer mixture) n ": 1.5361 5 4- (methylsulfonyl) -l, 2,3-triazole l (2,3) -carboxylic acid (N-ethyl-N-butyl) - -amide M.p. 60-62 ° C 10 (Isomer mixture) 4- (ethylthio) -5-methyl-l, 2,3-triazole l (2,3) -carboxylic acid dimethylamide (Isomer mixture) n ': 1.5333 4- (propyl-sulfonyl) -5-methyl-2,3- n ": 1.4967 triazol-l (2,3) -carboxylic acid, dipropyl -amide (Isomer mixture) 15 4- (propyl-sulfonyl) -5-methyl-2,3- triazol-l (2,3) -carboxylic acid (N-ethyl-N- -isopropyl) -amide (Isomer mixture) n: 1.4973 20 4- (2-propynylthio) -5-methyl-2,3- triazol-l (2,3) -carboxylic acid dimethyl- -amide (Isomer mixture) n ": 1.5568 4- (methylsulfonyl) -l, 2,3-triazole l (2,3) -carboxylic acid (N-ethyl-N- -isopropyl) -amide (Isomer mixture) n ": 14989 25 4- (ethyl-sulfonyl) -l, 2,3-triazole l (2,3) -carboxylic acid (N-ethyl-N- -isopropyl) -amide (Isomer mixture) n »: 1.5000 30 4- (l-methyl-propylsulfonyl) -l, 2,3- n ": 1.4959

-Thiazole-1 (2,3) -carboxylic acid (N-ethyl-N-isopropyl) -amide (mixture of isomers) 35

151

152

153

154

4- (ethylsulfonyl) -l, 2,3-triazole l (2,3) -carboxylic acid diisopropylamide (Isomer mixture) n ': 1.4952 4- (Isobutylsulfonyl) -1,2,3-triazole- n: 1.4925 1 (2,3) -carboxylic acid diisopropylamide 40 (Isomer mixture) 4- (butyl-sulfonyl) -l, 2,3-triazole n: 1.4935 l (2,3) -carboxylic acid diisopropylamide (Isomer mixture) 5-Methyl-4- (propylsulfonyl) -l, 2,3- ng: 1.4911

- Triazole-1 (2,3) -carboxylic acid diisopropyl-45

-amide (mixture of isomers)

155

156

157

158

159

160

4- (Isopropyl-thio) -5-methyl-l, 2,3-triazol-l (2,3) -carboxylic acid dimethyl- n ": 1.5254 -amide (Isomer mixture) 4- (Allylthio) -5-methyl-1,2,3-triazole-1 (2,3) -carboxylic acid dimethylamide (isomeric mixture) n ": 1.5439 50 4- (2-Cyano-ethylthio) -5-methyl-2,3- triazol-l (2,3) -carboxylic acid dimethyl- -amide n ": 1.5400 55 (Isomer mixture) 4- (methylthio) -5-propyl-l, 2,3-triazole l (2,3) -carboxylic acid dimethylamide n ": 1.5292 5-Ethyl-4- (methylthio) -l, 2,3-triazole l (2,3) -carboxylic acid dimethylamide n / a: 1.5370 60 5-Isopropyl-4- (methylthio) -l, 2,3- triazol-l (2,3) -carboxylic acid dimethyl- -amide n ": 1.5263

Compound sign

The name of the compound

Physical constant

161 5- (tert-Butyl) -4- (methylthio) -1,2,3-nj: 1,5271-triazole-1 (2,3) -carboxylic acid dimethylamide

The compounds of the present invention are generally colorless and odorless oils or crystalline materials having medium to high solubilities in allyl hydrocarbons, halogenated hydrocarbons such as chloroform and carbon tetrachloride, ketones such as acetone, carboxylic acid amides such as dimethylformamide, sulfoxides, , carboxylic acid nitriles such as acetonitrile, lower alcohols such as methanol and ethanol. The compounds of the invention are soluble in water only under certain conditions.

The compounds of formula I according to the invention may have the isomeric structure of formula A, B or C, wherein R 1, R ₂ , R ₃ , R 1 and n are as defined above.

In the preparation, when R ₂ is hydrogen, a mixture of A and C isomers may be formed.

Compounds having only structure A may be formed when R ₂ is alkyl.

However, as the structure is not yet fully elucidated, the compounds of the present invention are preferably referred to in the context of the present invention as 1,2,3-triazole-1 (2,3) -carboxylic acid amides, but always from one of structures A, B or C, or it may be a mixture of isomers.

Said mixtures may optionally be separated by conventional methods, for example, chromatography; this can be influenced by the choice of specific solvents to quantitatively form one or the other isomer.

However, since isomeric mixtures are particularly effective from a biocidal point of view, separation of the isomeric mixtures is generally not advantageous.

The following examples illustrate the agents of the present invention and their uses.

Example 5

Powder composition% by weight of 4- (propylsulfonyl) -1,2,3-triazole-1 (2,3) carboxylic acid dipropylamide% by weight of lignin sulfonic acid calcium salt% by weight of tetraethylene glycol nonylphenyl ether mono-benzoate ester weight% colloid silicic acid example

Powder composition% by weight of 4-methyl-5- (methylthio) -1,2,3-triazole-1 (2,3) carboxylic acid dimethylamide% by weight of lignin sulfonic acid calcium salt% by weight of the mono-sulfonic ester of tetraethylene glycol nonylphenyl ether ammonium salt

Example 7

Composition of emulsion concentrate% by weight 4- (propylsulfonyl) -1,2,3-triazole-1 (2,3) carboxylic acid dipropylamide% by weight tonsil weight% cellulose weight% fatty acid condensation product based wetting agent

184,696

Example 8

Emulsion Concentrate Composition% by weight 4-methyl-5- (methylthio) -1,2,3-triazole-1 (2,3) carboxylic acid dimethylamide% by weight 5% by weight cellulose weight% fatty acid condensation based wetting agent

Example 9

Composition of emulsion concentrate. θ% by weight of 4- (propylsulfonyl) -1,2,3-triazole-1 (2,3) carboxylic acid dipropylamide 70% by weight of xylene by weight of isophorone by weight of alkyl polyglycol ether, alkyl phenol polyglycol ether and fatty acid an emulsifier combination consisting of polyglycolester

Example 70

Composition of emulsion concentrate% by weight 4-methyl- (5-methylthio) -1,2,3-triazole-1 (2,3) -20-carboxylic acid dimethylamide% by weight xylene by weight% by weight of isophorone from alkyl polyglycol ether, alkyl emulsifier combination of 25-phenol polyglycolether and polyglycol fatty acid

The spray liquors and dressing fluids used in the following application examples were prepared from an emulsion concentrate having the same composition as in Example 9 except for the quality of the active ingredient.

Example 77

Agents containing compounds of the invention listed in the following table were sprayed in a greenhouse before hatching Digitaría s. Sorghum h., For cotton and maize plants, at a rate of 5 kg of active ingredient / hectare (500 liters of water / hectare). The results were evaluated 3 weeks after treatment and evaluated as follows:

= no effect and 40 = plants dead.

As can be seen from the table, the weeds were killed and the crop plants were not damaged by the agents of the invention. In contrast, the comparator used to kill the crop. 45

The active ingredients (symbol of the compound) used are ^Kuk ° - Cotton ^Di 8 ¹ 'rica tana s. wow h.

Active ingredients of the agents used (symbol of the compound)

Maize

Cotton 8 · ™

Sorghum h.

67. 68 69

70

71

72:

0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4

78. 0

79.0

80.0

81. 0

82. 0

84. 0

85.0

96. 0

99.0

101. 0

102. 0

103. 0

104. 0

105.0

106. 0

107. 0

108. 0

109. 0

110.0

111. 0

112. 0

113. 0

114. 0

115. 0

116. 0

117. 0

118. 0

119. 0

120.0

121. 0

122. 0

123. 0

124. 0

125. 0

126. 0

127. 0

128. 0

129. 0

130.0

131. 0

132. 0

133. 0

134. 0

135. 0

136. 0

137. 0

138. 0

140.0

141. 0

142. 0

143. 0

144. 0

145.0

146. 0

147. 0

148. 0

149. 0

150.0

151. 0

152. 0

153. 0

4 4 0 4 4 0 4 4 0 4 4 0 4 4 0 4 4 0 4 4 0 4 4 0 4 4 0 4 4 0 4 4 0 4 4 0 4 4 0 4 4 0 4 4 0 4 4 0 4 4 0 4 4 0 4 4 0 4 4 0 4 4 0 4 4 0 4 4 0 4 4 0 4 4 0 4 4 0 4 4 0 4 4 0 4 4 0 4 4 0 4 4 0 4 4 0 4 4 0 4 4 0 4 4 0 4 4 0 4 4 0 4 4 0 4 4 0 4 4 0 4 4 0 4 4 0 4 4 0 4 4 0 4 4 0 4 4 0 4 4 0 4 4 0 4 4 0 4 4 0 4 4 0 4 4 0 4 4 0 4 4 0 4 4 0 4 4 0 4 4 0 4 4 0 4 4 0 4 4 0 4 4

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184,696

The active ingredients of the agents used (symbol of the compound) are ^Kuk ° - Cotton _κ ^5θΓ §nca sana. Hum. h.

154. 0

155. 0

156. 0

157. 0

Reference substance N-ethyl-4-propyl-3- 3

- (propylsulfonyl) -1H-1,2,4-triazol-l-carboxamide

without treatment

Example 72

Prior to emergence, the plants listed in the table below were treated in a greenhouse with agents containing the following compounds in an amount of 3 kg of active ingredient / hectare. Three weeks after treatment, the agents of the invention were found to have very good selectivity, but the weed activity was excellent. The agent used for comparison did not show this selectivity.

The evaluation was carried out as follows:

= completely destroyed = 90% damage = 80% damage = 70% damage = 60% damage = 50% damage = 40% damage 7 · = 30% damage = 20% damage = 10% damage 10 = no damage

Active ingredient used (symbol of the compound) potato nya maize rica Soy Cotton Bush- puppet Pea Elope- aequalis myosoi- des Avena fatua First 10 10 10 10 10 10 0 0 65th 10 10 10 10 10 10 0 0 67th 10 10 10 10 10 10 0 0 76th 10 10 10 10 10 10 0 0 Comparative agent N-ethyl-4-propyl-3- (propylsulfonyl) - -lH-l, 2,4-triazol-l-carboxamide 5 1 2 1 1 2 0 0 without treatment 10 10 10 10 10 10 10 10 (Continuation of the table) The employee Echi- Digi Taria Cype- ms Sorg- hum active ingredient (sign of the compound) Senecio Setaria Poa noch- loa First 0 0 0 0 0 0 0 65th 0 0 0 0 0 0 0 67th 0 0 0 0 0 0 0 76th 0 0 0 0 0 0 0 Comparative agent N-ethyl-4-propyl-3- (propylsulfonyl) -lH 0 0 0 0 0 0 0 -1,2,4-triazole-1-carboxamide without treatment 10 10 10 10 10 10 10

Example 13 50

Young cotton plants at 5-7 leaf stage were treated with agents containing the following active ingredients. Spray broth was applied at 500 liters / hectare. After a few days, we determined the percentage of decapitated leaves. The results are shown in the table below.

Active ingredient used (symbol of the compound)

Application rate g / ha

Unmount%

Example 14

Young cotton plants at the 5-7 leaf stage were treated with agents containing the following active ingredients. For each treatment, 4 plants with a total of 24-25 leaves were available. Spray broth was applied at 500 liters / hectare. After a few days, we determined the percentage of fallen leaves. The results are shown in the table below.

Active ingredient used (symbol of the compound)

Application rate g / ha

Unmount%

Second 500 48.0 58th 500 12.0 Second 500 40.0 2000 50.0 Comparative agent 65th 500 13.6 Tri-n-butyl tritio- 500 4.7 67th 500 28.0 65 phosphates 2000 4.7

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Example 75

Rooted willow cuttings at the stage of 11-14 leaf deciduous plants were treated with agents containing the following active ingredients in a similar manner as in Example 8. For each treatment 3 plants were available, with a total of 24-25 leaves.

Application rate g / ha

Drug used (active ingredient symbol)

Second 500 15.4 67th 2000 61.5 68th 2000 61.5 Comparative agent Tri-n-butyl tritio- phosphate 500 7.7 76 examples

Cotton plants at 6-8 adult leaf stage were treated with agents containing the following active ingredients. Spray broth was applied at 500 liters / hectare. For each treatment, 4 plants were available with a total of 28 leaves. A few days

we found the percentage of fallen leaves. The results are shown in the table below. The active ingredient of the agent used is ^Dose '(sign of the compound) g / ha defoliation % Second 2000 71.4 74th 2000 59.3 80th 2000 55.6

Example 17

Cotton plants at 7-8 developed leaf stage were treated with agents containing the following active ingredients. For each treatment, 4 plants were available with a total of 25 to 26 leaves. Spray leaves were applied at 500 liters / hectare. After a few days, we determined the percentage of fallen leaves. The results are shown in the table below

shows. Drug used (active ingredient symbol) Dose g / ha of active substance defoliation % Second 2000 72 58th 2000 76 73rd 2000 88 84th 2000 72 88th 2000 80

Example 18

The agents of the invention were used as aqueous dispersions at a concentration of 0.04%.

With the aforementioned formulations, the lid of the Petri dishes was sprayed with 4 mg of spray juice / cm ² . 25 to 25 adult Mediterranean fruit flies (Ceratitis capitata) were exposed to the said spray coating under long day conditions in a closed Petri dish for 24 hours. The 12 criteria for judging the effect were the percent mortality of flies after 24 hours. The table below illustrates the percentage mortality.

Unmount%

Agent used Concentration of 5 active ingredients of Mortality after 24 hours (compound sign)%

Second Third 0.04 0.04 100 100 10 4th 0.04 68 5th 0.04 95 20th 0.04 100 21st 0.04 90 22nd 0.04 52 15 23rd 0.04 90 24th 0.04 45 25th 0.04 80 26th 0.04 75 27th 0.04 95 20 28th 0.04 75 29th 0.04 60 30th 0.04 56 31st 0.04 52 32nd 0.04 20 25 52nd 0.04 100 57th 0.04 79 73rd 0.04 100 74th 0.04 100 86th 0.04 100 30 87th 0.04 100 89th 0.04 100 144th 0.04 100 147th 0.04 100 158th 0.04 100 35 159th 0.04 100 160th 0.04 100 without treatment 0

Example 79

The agents of the invention were used as aqueous dispersions at a concentration of 0.04%.

With the aforementioned compositions, the lid and bottom of the petri dishes were sprayed with 4 mg of spray juice / cm ² . Ten to twelve to seventeen-day-old German cockroaches (Blat45 tella germanica) were exposed to the spray liquid coating in laboratory Petri dishes under long-day conditions. The effect was assessed by the percentage of cockroach deaths after 48 hours. The table below illustrates the percent mortality outcome.

Agent used Concentration of active ingredient Mortality active ingredient after 48 hours (compound sign)%

2. 0.04 100

3. 0.04 100

4. 0.04 100

5. 0.04 100

20. 0.04 100

21. 0.04 100

22. 0.04 100. 0.04,100

24. 0.04 20

25th 0.04,100

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Drug used Concentration of active ingredient Mortality active ingredient after 48 hours (compound sign)%

26th 0.04 100 27th 0.04 80 28th 0.04 100 29th 0.04 100 30th 0.04 100 31st 0.04 100 32nd 0.04 100 52nd 0.04 100 57th 0.04 100 73rd 0.04 100 74th 0.04 100 86th 0.04 100 87th 0.04 100 89th 0.04 100 144th 0.04 100 147th 0.04 100 155th 0, O4 100 156th 0.04 100 157th 0.04 100 158th 0.04 100 159th 0.04 100 160th 0.04 100

Example 20

The agents of the invention were used as aqueous dispersions at a concentration of 0.04%.

The bean plants (Vicia faba) planted in pots planted in pots and flooded with a strong population of black bean aphid (Aphis fabae) were sprayed with rainwater. The plants were then kept in a laboratory for 48 hours under long day conditions.

The effect was evaluated on the percentage of aphids at 48 hours. The table below illustrates the percent mortality rates.

Drug used Concentration of active ingredient Mortality active ingredient after 48 hours (compound sign)%

Second 0.04 100 Third 0.04 100 4th 0.04 100 5th 0.04 100 20th 0.04 100 21st 0.04 100 22nd 0.04 60 23rd 0.04 90 24th 0.04 90 25th 0.04 100 26th 0.04 90 27th 0.04 95 28th 0.04 90 29th 0.04 100 30th 0.04 100 31st 0.04 100 32nd 0.04 100 52nd 0.04 100 57th 0.04 100 73rd 0.04 100 74th 0.04 100

Active ingredient used (symbol of the compound) Concentration of active ingredient Mortality in 24 hours, % % 86th 0.04 100 87th 0.04 100 89th 0.04 100 144th 0.04 100 147th 0.04 100 155th 0.04 100 156th 0.04 100 157th 0.04 100 158th 0.04 100 159th 0.04 100 160th 0.04 100

Example 27

The agent of the invention and the comparator were used in the form of aqueous dispersions at a concentration of 0.0012%. The above formulations were sprayed on the lid and bottom of Petri dishes at 4 mg of spray liquid / cm ² , and 10 to 10 twelve to seventeen-day German cockroaches (Blattella germanica) in closed Petri dishes were exposed to these spray coatings under laboratory conditions for long days. . The effect was assessed by the percentage of cockroach deaths after 48 hours. The table below illustrates the percentage mortality.

Active ingredient used (symbol of the compound) Concentration of active ingredient% Mortality after 48 hours% Second 0.0012 100 Comparative agent o-isopropoxy-phenylmethyl 0.0012 90 carbamate 2,2-dimethyl-1,3-benzo 0.0012 90

dioxo-4-yl-methyl-carbamate

Example 22

The agent of the invention and the comparator were used as an aqueous dispersion at a concentration of 0.00025.

With the aforementioned compositions, the lid and bottom of the petri dishes were sprayed with 4 mg of spray juice / cm ² . 10 to 10 young cotton wool bunnies (Dysdercus cingulatus) (stage 3 of weaning) were exposed to said spray coating for 48 hours in a closed petri dish in a laboratory under long day conditions.

The effect was evaluated on the basis of the death of leaf bugs after 48 hours. The table below illustrates the percentage mortality.

Active ingredient used (symbol of the compound) Concentration of active ingredient% mortality After 48 hours % Second 0.00025 95 Comparative agent 1-naphthyl methyl carbamate 0.00025 60

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184,696

Example 23

The agents according to the invention and for comparison purposes were used in the form of aqueous emulsions at the desired concentration of active ingredient.

With the aforementioned compositions, the lid and bottom of the petri dishes were sprayed with 4 mg of spray juice / cm ² . 10 to 10 young cotton bud moths (Dysdercus cingulatus, stage 3) were exposed to said spray coating in a closed laboratory in Petricese for 42 hours under long day conditions.

The effect was evaluated by the percentage Knock-Down effect at 1, 30, and 60 minutes, and by the loss of leaf bugs after 42 hours.

Knock-Down

Active ingredient used (symbol of the compound) Concentration of active ingredient% 1 effect 30 minute after 60 mortality After 42 hours % Second 0.01 100 100 100 100 0,005 100 100 100 100 52nd 0.01 - 100 100 100 0,005 - - 100 100 Comparative agent 2- (methoxycarbonyl) -l-methyl-nonyl-dimethyl- 0.01 100 100 100 100 -phosphate 0,005 - 100 100 100 5-benzyl-3-furyl-methyl (+ -) - cis, trans- 0.01 - 95 95 85 chrysanthemate 0,005 - - 30 85 • 25 Example 24 The employed s agent Treatment of barley seeds Helminthosporium spec. against The active g active mother g / 100 kg Effect,% The barley seed naturally contaminated by Helminthosporium gramineum is treated untreated or in the amounts shown in the table below. (compound sign · e) 30 28th 20

was poured into pots filled with earth and allowed to germinate at a temperature below + 16 ° C. Who-

after emergence, the plants were illuminated for 12 hours daily. After about 5 weeks, in each experiment, infected plants were counted and similarly 35 29th 20 50 70 total hatched plants. The fungicidal effect the following 30th 20 87 we calculated as follows: 50 98 % effect = 100 - infections in the untreated · 100 infections in the untreated 40 31st 20 56 50 79 The agent used 32nd 20 The active g active substance / 100 kg Effect% - (sign of compound) 45 50 58 Second 20 _ 33rd 20 - 50 100 50 70 4th 20 69 34th 20 - 50 94 50 50 87 7th 20 54 ' 35th 20 50 90 50 90 19th 20 55 . 37th 20 - 50 90 50 94 20th 20 97 38th 20 - 50 100 60 50 77 21 20 82 39th 20 100 50 93 50 100 25th 20 67 52nd 20 - 50 90 65 50 70

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Active ingredient used (symbol of the compound) g active substance / 100 kg Effect% Active ingredient used (symbol of the compound) g active substance / 100 kg Effect% 57th 20 100 5 33rd 10 - 50 - 20 70 58th 20 95 34th 10 - 50 100 10 20 72 59th 20 - 35th 10 - 50 70 20 87 60th 20 36th 10 - 50 100 15 20 87 61st 20 _ 37th 10 - 50 100 20 82 64th 20 _ 20 38th 10 85 50 100 20 94 143rd 20 76 40th 10 _ 50 87 25 20 90 Example 25 59th 10 - Treatment of wheat seeds against Tilletia caries 20 90

Wheat seed per kilogram of the stone angina pests

(Tilletia caries) (3 g). Untreated or 30 in the table 61st 10 20 70 in quantities treated with wet beard ends printed in Petri dishes containing +12 74th 10 - Incubate at <3 ° C for 3 days. Then out- 20 90

we took the eyes and the petri dishes left over

were further incubated with rock spores at about 12 'Con. After 10 days, the spores were examined for germination. 35 82nd 10 20 90 The fungicidal effect was calculated as follows: germination percentage of hands · 100 83rd 10 - % effect = 100 20 90 gutters with untreated 40 88th 10 _ The agent used 20 90 The active g active substance / 100 kg Effect% (sign of compound) 89th 10 - 45 20 90 4th 10 78 20 93 90 10 - 20 90 19th 10 - 20 90 50 91st 10 - 20 90 28th 10 - 20 90 92nd 10 - 20 90 29th 10 - 55 20 90 95th 10 - 20 90 30th 10 - 20 90 96th 10 _ 60 20 90 31st 10 68 20 100 97th 10 - 20 90 32nd 10 27 20 100 65

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Active ingredient used (symbol of the compound) % Of active substance (sprayed with dripping water) Effect% 127th 10 20 90 5 128th 10 20 90 10 129th 10 20 90 130th 10 20 90 15 133rd 10 20 90 134th 10 20 90 20 135th 10 20 90 25 136th 10 20 90 137th 10 20 90 30 138th 10 20 90 144th 10 20 50 90 35 145th 10 20 92 90 40 146th 10 20 12 90 147th 10 53 45 20 90 149th 10 20 90 150th 10 20 90 50 Example 26 Spray treatment of rice seedlings Piricularia oryzae 55

against

Young rice plants were sprayed with dripping water with formulations containing the active ingredient in the concentration given in the table below. After drying of the spray coating, the treated plants, as well as the untreated plants, were inoculated by spraying a suspension (about 200,000 spores / ml) of spores of the leaf spot pathogen (Piricularia oryzae) and incubated in a greenhouse at + 25-627 ° C. After 5 days, we determined that 65% of the surface of the leaves was infected. From these data, the fungicidal effect was calculated as follows:

, "Contamination of hands« 100% effect = 100 - ———---—-— contamination with untreated

Active ingredient used (symbol of the compound) % Of active substance (sprayed with dripping water) Effect, i Second 0.1 91 0.02 65 0,004 - 16th 0.1 80 0.02 - 0,004 - 20th 0.1 85 0.02 - 0,004 - 33rd 0.1 65 0.02 - 0,004 - 35th 0.1 65 0.02 - 0,004 - 52nd 0.1 90 0.02 - 0,004 - 60th 0.1 70 0.02 - 0,004 - 61st 0.1 91 0.02 58 0,004 - 65th 0.1 92 0.02 57 0,004 - 67th 0.1 100 0.02 60 0,004 - 68th 0.1 90 0.02 - 0,004 - 69th 0.1 93 0.02 45 0,004 - 70th 0.1 89 0.02 - 0,004 - 71st 0.1 93 0.02 55 0,004 -

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184,696

Active ingredient used (symbol of the compound) % Of active substance (sprayed with dripping water) Effect% Active ingredient used (symbol of the compound) % Of active substance (sprayed with dripping water) Effect,.% 72nd 0.1 87 5 89th 0.1 87 0.02 - 0.02 - 0,004 - 0,004 - 73rd 0.1. 98 91st 0.1 94 0.02 80 10 0.02 087 0,004 45 0,004 62 74th 0.1 97 92nd 0.1 91 0.02 75 0.02 73 0,004 45 15 0,004 31 75th 0.1 97 96th 0.1 100 0.02 87 0.02 89 0,004 73 20 0,004 54 76th 0.1 93 100th 0.1 75 0.02 80 0.02 69 0,004 65 0,004 - 77th 0.1 98 25 One hundred and first 0.1 94 0.02 87 0.02 62 0,004 60 0,004 12 78th 0.1 93 128th 0.1 98 0.02 75 30 0.02 65 0,004 45 0,004 30 79th 0.1 90 129th 0.1 98 0.02 - 0.02 50 0,004 - 35 0,004 25 80th 0.1 90 132nd 0.1 99 0.02 - 0.02 50 0,004 - 40 0,004 57 81st 0.1 90 133rd 0.1 100 0.02 - 0.02 89 0,004 - 0,004 65 82nd 0.1 90 45 134th 0.1 100 0.02 - 0.02 85 0,004 - 0,004 78 83rd 0.1 90 135th 0.1 100 0.02 - 50 0.02 100 0,004 - 0,004 93 85th 0.1 99 136th 0.1 100 0.02 87 0.02 80 0,004 80 55 0,004 70 86th 0.1 96 137th 0.1 100 0.02 20 0.02 80 0,004 10 60 0,004 30 88th 0.1 80 138th 0.1 99 0.02 35 0.02 86 0,004 20 0,004 75

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Active ingredient used (symbol of the compound) % Of active substance (sprayed with dripping water) Effect% 140th 0.1 83 0.02 - 0,004 - 141st 0.1 67 0.02 - 0,004 - 142nd 0.1 71 0.02 17 0,004 17 143rd 0.1 90 0.02 - 0,004 - 144th 0.1 90 0.02 - 0,004 - 145th 0.1 90 0.02 - 0,004 - 146th 0.1 90 0.02 - 0,004 - 155th 0.1 90 0.02 - 0,004 - 156th 0.1 90 0.02 - 0,004 -

Example 27

Treatment of spraying tomato seedlings against Bortrytis cinerea

Young tomato plants were sprayed with dripping water with formulations containing the active ingredient in the concentrations indicated in the table below. After drying of the spray coating, the treated plants as well as untreated plants were inoculated by spraying a suspension containing the spores of the gray mold pathogen (Botrytis cinerea) (about 1 million / ml of fruit juice solution) and incubated in a greenhouse at about 20 ° C. After disruption of untreated plants (= 100% infestation), the degree of infestation of the treated plants was determined and the fungicidal effect was calculated as follows:

contamination of hands · 100 effect% = 100 ---———-: -—: -— contamination with untreated

Active ingredient used (symbol of the compound) % Of active substance (sprayed with dripping water) Effect% 20th 0,025 50 59th 0,025 72 64th 0,025 78

2 & example

Limit test for root-knot nematodes (Meloidogyne sp.)

An appropriate amount of a powder formulation consisting of 20% active ingredient and 80% talc was uniformly mixed with heavily contaminated soil with rootworm nematodes. After a waiting period of 3 days, the treated soil was placed in two 0.5 liter clay pots, 10 seeds of Guntruud cucumber seeded per cup and grown in a greenhouse at 24-27 ° C for 28 days. The roots of the cucumbers were then washed, tested for nematode infestation in a water bath, and the percentage reduction in infestation achieved by the agent applied compared to untreated control was determined.

The active ingredients used, the amount used and the reduction in infestation are listed in the table below.

The nematocidal efficacy was calculated as follows:

A = contamination in untreated controls;

B = infection after treatment

The agent used is the concentration of the active ingredient

active ingredient (sign of the compound) 200 mg mg / liter of earth 100 mg 50 mg Third 100 100 92 4th 100 100 98 21st 100 100 100 22nd 100 100 100 23rd 100 100 93 24th 100 100 100 25th 100 98 50 26th 100 97 96 27th 100 100 98 28th 100 93 63 29th 100 99 * 57 30th 100 100 71 31st 100 97 93 32nd 99 98 - 33rd 100 100 95 34th 92 69 42 35th 95 95 64 36th 100 99 93 37th 100 99 - 38th 97 53 - 44th 100 100 - 52nd 93 97 81 59th 100 95 - 63rd 100 92 -

Example 29

Treatment of vine leaves against Plasmopora viticola

Young grape vines with about 5-8 leaves were sprayed in dropsy water with formulations containing the active ingredient in the following table, after drying of the spray coating, the lower part of the leaves was sprayed with an aqueous suspension of fungal sporangia (about 20,000 / ml) and immediately incubated.

-181

184,696. 10 weeks after sowing, we counted the sick bunches and calculated the effect using the following formula:

infection by the operator · 100 effect% = 100 - _r * ---—-— infection by the untreated

22-24 ° C and in a water vapor atmosphere as saturated as possible. From day 2, the humidity of the air was reduced to the normal value for 3 to 4 days (30-70% saturation) and then a saturated water vapor atmosphere was created for one day. The percentage of fungal infested surface of each leaf was then recorded and treated to determine fungicidal activity.

calculated from each: the tear value is the the following effect% - 100 - contamination of the hands • 10 infection with the untreated The agent used Active substance % Effect % active ingredient (sign of the compound) 71st 0,025 48 128th 0,025 100 130th 0,025 75 132nd 0,025 92 133rd 0,025 77 134th 0,025 83 139th 0,025 91 140th 0,025 99 141st 0,025 98 142nd 0,025 99 Example 30 Treatment of pumpkin leaf Erysiphe cichoracearum against The active ingredient is given as% in the table below proportion preparations for dripping water sprayed young pumpkin plants after inoculation of the powder with dry spores of powdery mildew (Erysiphe cichoracearum), incubated at 24 ° C, and after 1 week, we estimated the percentage of the infected powdery mildew on the total surface area of the leaves- puts it down. The fungicidal effect was calculated as follows: effect% = 100 - contamination of the hands • 100 infection with the untreated The active ingredient used Active substance% Effect % (sign of compound) 67th 0,025 97 68th 0,025 85 72nd 0,025 90 74th 0,025 100 78th 0,025 90 103rd 0,025 70 146th 0,025 92 147th 0,025 94 154th 0,025 90

Example 31

Treatment of oat seed against Ustilago avenae (field experiment) 60

Oat seed was dipped in a suspension of spores of oat powder (Ustillago avenae) and subjected to alternating pressure and vacuum in a vacuum desiccator. After the seed has dried, the powder formulation used in Example 28 is 65

Active ingredient used (symbol of the compound)

Active substance g / 100 kg

Effect%

29th 10 220 55 59th 110 82 20 - 63rd 20 70 20 -

PATENT CLAIMS

Claims (123)

A pesticidal agent, in particular having a herbicidal, insecticidal, acaricidal, fungicidal and / or nematocidal action, characterized in that it comprises 10 to 80% by weight of a compound of formula (I) 1,2,3-triazole carboxylic acid amide derivative of the formula R 1 is C 1 -C 8 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, or phenyl (C 1 -C 3 alkyl); R 1 is hydrogen or C 1-4 alkyl; R ₃ is hydrogen, C 1 -C 10 alkyl, halo (C 1 -C 4 alkyl) or C 2 -C 6 alkenyl; R 4 is C 1 -C 10 alkyl, C 2 -C 6 alkenyl, C 4 -C 6 cycloalkyl, halo-C 1 -C 4 alkyl, phenyl-C 1 -C 3 alkyl, or optionally C 1 -C 4 alkyl or a monosubstituted phenyl group; R ₃ and R together with the nitrogen atom represent a pyrrolidino, piperidino, hexahydroazepino or morpholino group and π is 0, 1 or 2, their isomers or mixtures of their isomers with a liquid and / or solid excipient, preferably a mineral, and optionally a surfactant. Preferably with fatty acid methyl tauride, calcium salt of lignin sulfonic acid, alkylphenol polyglycol ether or fatty acid condensation product-based. Embodiment according to claim 1, characterized in that it is a compound of formula (I) Containing a 1,2,3-triazole carboxylic acid derivative, wherein R 1 is C 1-8 alkyl or phenyl (C 1-3 alkyl); R ₂ is hydrogen or methyl; R ₃ is alkyl or alkenyl having up to 6 carbon atoms; and R 1 is alkyl, alkenyl or cycloalkyl having up to 6 carbon atoms, phenyl (C 1 -C 3) alkyl, or phenyl; or R ₃ and R 4 together with the nitrogen atom are hexahydroazepino and n is 2. -191 184,696 Embodiment according to claim 1, characterized in that it is a compound of formula (I) Containing a 1,2,3-triazole carboxylic acid amide compound of the formula wherein Ri is methyl, ethyl, propyl, allyl or propyn-2-yl, _5; R ₃ is hydrogen, methyl, ethyl or propyl; R ₃ is hydrogen or methyl, R1 is methyl and jq is 0. 4. An agent according to claim 1, which is of formula (I) Containing a 1,2,3-triazole carboxylic acid amide derivative of the formula: R 1 is C 1-8 alkyl, allyl, propin-2-yl, or phenyl (C 1-3 alkyl); R ₂ is hydrogen or methyl; R ₃ is hydrogen; 20 R4 is alkyl having up to 4 carbon atoms and n is 0. 5. An embodiment of the agent of claim 1, wherein the compound of formula I is 4- (propylsulfonyl) -1,2,3-triazole-l (2,3) -carboxylic acid dipropylamide. contain. 6. An agent according to claim 1 wherein the compound of formula I is 4-methyl-5- (methylthio) -1,2,3-triazole-1 (2,3) -carboxylic acid dimethyl-. containing amide. 30 7. The agent of claim 1 wherein the compound of formula I is 4- (methylthio) -1,2,3-triazole-1 (2,3) -carboxylic acid methylamide. 8. An agent according to claim 1 wherein the compound of formula I is 4- (methylthio) -1,2,3-triazole-1 (2,3) -carboxylic acid ethylamide. contain. 9. An agent according to claim 1 wherein the compound of formula I is 40 4- (methylthio) -1,2,3-triazole-1 (2,3) -carboxylic acid (2-). chloranilide). 10. The agent of claim 1, wherein the compound of formula I is 4- (methylthio) -1,2,3-triazole-1 (2,3) -carboxylic acid (3-methyl). - contains 45 anilides). 11. An agent according to claim 1 wherein the compound of formula I is 4- (methylthio) -1,2,3-triazole-1 (2,3) -carboxylic acid (4-methylanilide). ). 50 12. The agent of claim 1 wherein the compound of formula (T) is 4- (methylthio) -1,2,3-triazole-1 (2,3) -carboxylic acid allylamide. . 13. An agent according to claim 1 wherein the compound of formula I is 4- (methylthio) -1,2,3-triazole-1 (2,3) -carboxylic acid dimethylamide. 14. The agent of claim 1, wherein the compound of formula I is θθ 4- (ethylthio) -1,2,3-triazole-1 (2,3) -carboxylic acid methylamide. contain. 15. The agent of claim 1, wherein the compound of formula I is 4- (propylthio) -1,2,3-triazole-1 (2,3) -carboxylic acid methylamide. 16. An agent according to claim 1 wherein the compound of formula I is 4- (isopropylthio) -1,2,3-triazole-1 (2,3) -carboxylic acid methylamide. 17. An agent according to claim 1 wherein the compound of formula I is 4-butylthio-1,2,3-triazole-1 (2,3) -carboxylic acid methylamide. 18. An agent according to claim 1 wherein the compound of formula I is 4- (1-methylpropylthio) -1,2,3-triazole-1 (2,3) -carboxylic acid methyl-. containing amide. 19. The agent of claim 1 wherein the compound of formula I is 4- (allylthio) -1,2,3-triazole-1 (2,3) -carboxylic acid methylamide. . 20. The agent of claim 1 wherein the compound of formula I is 4- (1-methylpropylthio) -1,2,3-triazole-1 (2,3) -carboxylic acid methyl-. containing amide. 21. The agent of claim 1 wherein the compound of formula I is 4- (isopropylthio) -1,2,3-triazole-1 (2,3) -carboxylic acid methylamide. 22. An agent according to claim 1 wherein the compound of formula I is 4- (butylthio) -1,2,3-triazole-1 (2,3) -carboxylic acid methylanide. 23. An agent according to claim 1 wherein the compound of formula (I) is 4- (2-propynylthio) -1,2,3-triazole-1 (2,3) -carboxylic acid methylamide. . 24. The agent of claim 1 wherein the compound of formula I is 4- (benzylthio) -1,2,3-triazole-1 (2,3) -carboxylic acid methylamide. 25. The agent of claim 1 wherein the compound of formula I is 4- (methylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid dimethylamide. 26. The agent of claim 1 wherein the compound of formula I is 4- (methylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid methylamide. 27. The agent of claim 1 wherein the compound of formula (I) is 4- (methylsulfinyl) -1,2,3-triazole-1 (2,3) -carboxylic acid methylamide. 28. The agent of claim 1, wherein the compound of formula I is 4-methyl-5- (methylthio) -1,2,3-triazole-1 (2,3) -carboxylic acid methyl-. containing amide. 29. The agent of claim 1 wherein the compound of formula (I) is 4- (methylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid dimethylamide. 30. The agent of claim 1 wherein the compound of formula (I) is 4- (methylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid diethylamide. -201 184,696 31. The agent of claim 1 wherein the compound of formula I is 4- (isopropylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid methylamide. 32. The agent of claim 1 wherein the compound of formula (I) is 4- (isopropylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid dimethylamide. 33. The agent of claim 1 wherein the compound of formula I is 4- (isopropylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid diethylamide. 34. The agent of claim 1 wherein the compound of formula (I) is 4- (propylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid methylamide. 35. The agent of claim 1 wherein the compound of formula I is 4- (propylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid * dimethylamide. . 36. An agent according to claim 1 wherein the compound of formula (I) is 4- (propylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid diethylamide. 37. An agent according to claim 1, wherein the compound of formula I is 4- (propylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid (Netyl-N). -propyl) -amide. 38. The agent of claim 1, wherein the compound of formula I is 4- (methylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid (N -propyl) -amide. 39. The agent of claim 1, wherein the compound of formula I is 4- (methylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid N-methylanilide. . 40. The agent of claim 1 wherein the compound of formula (I) is 4- (isopropylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid N-ethylanilide. . 41. An agent according to claim 1, wherein the compound of formula I is 4- (propylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid N-anilide. . 42. The agent of claim 1 wherein the compound of formula I is 4- (isopropylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid (N-ethyl). Contains N-propyl) -amide. 43. An agent according to claim 1, characterized in that it is a compound of formula (I) Contains 4- (butylthio) -1,2,3-triazole-1 (2,3) -carboxylic acid dimethylamide. 44. The agent of claim 1 wherein the compound of formula I is 4- (isobutylthio) -1,2,3-triazole-1 (2,3) -carboxylic acid dimethylamide. 45. An agent according to claim 1 wherein the compound of formula I is 4- (butylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid dimethylamide. 46. An agent according to claim 1, wherein the compound of formula I is 4- (butylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid diethylamide. 47. The agent of claim 1, which is as a compound of formula (I) Contains 4- (isobutylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid dimethylamide. ₅ 48. An agent according to claim 1, embodiment, wherein (I) is used as compound containing 4- (butyl-sulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid diethylamide. 40. The agent according to embodiment of Claim 1, wherein _10, characterized in that the compound of formula (I) is 4- (ethylsulfonyl) -l, 2,3-triazol-l (2,3) comprises -karbonsavdimetil amide. 50. The agent of claim 1 wherein the compound of formula (I) is 4 g of 4- (ethylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid diethylamide. 51. The agent of claim 1 wherein the compound of formula I is 4- (1-methylpropylsulfonyl) -1,2,3-triazole-1 (2,3) 20 carboxylic acid. contains dimethylamide. 52. The embodiment of claim 1 wherein the compound of formula I is 4- (butylthio) -1,2,3-triazole-1 (2,3) -carboxylic acid diethylamide. 54. The agent of claim 1, wherein the compound of formula I is 4- (1-methylpropylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid. containing diethyl amide. 55. An embodiment of the agent of claim 1, wherein Characterized in that it is a compound of formula (I) Contains 4- (benzylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid dimethylamide. 56. The agent of claim 1, which is as a compound of formula (I) Contains 4- (ethylthio) -1,2,3-triazole-1 (2,3) -carboxylic acid dimethylamide. 57. The agent of claim 1, wherein the compound of formula I is 4- (ethylthio) -1,2,3-triazole-1 (2,3) -carboxylic acid diethylamide. Contains 40. 58. The agent of claim 1 wherein the compound of formula I is 4- (isobutylthio) -1,2,3-triazole-1 (2,3) -carboxylic acid diethylamide. 45 59. An embodiment of the agent of claim 1, wherein the compound of formula I is 4- (1-methylpropylthio) -1,2,3-triazole-1 (2,3) -carboxylic acid dimethyl-. containing amide. 60. The agent of claim 1, wherein 50 as a compound of formula (I) Contains 4- (1-methylpropylthio) -1,2,3-triazole-1 (2,3) -carboxylic acid diethylamide. 61. The agent of claim 1, which is as a compound of formula (I) 55 Contains 4- (benzylthio) -1,2,3-triazole-1 (2,3) -carboxylic acid dimethylamide. 62. The agent of claim 1, wherein the compound of formula (I) is 4- (benzylthio) -1,2,3-triazole-1 (2,3) -carboxylic acid diethyl-amide. 63. The agent of claim 1 wherein the compound of formula (I) is 4- (propylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid isopropylamide. -211 184,696 64. The agent of claim 1 wherein the compound of formula (I) is 4- (propylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid dibutylamide. 65. The agent of claim 1, wherein the compound of formula (I) is 4- (propylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid pyrrolidide. 66. The agent of claim 1, wherein the compound of formula I is 4- (propylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid diallylamide. 67. The agent of claim 1 wherein the compound of formula I is 4- (propylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid-morpholide. 68. The agent of claim 1, wherein the compound of formula I is 4- (butylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid (Netyl-N). -propyl) -amide. 20 69. The agent of claim 1 wherein the compound of formula I is 4- (isobutylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid (N-ethyl). Contains N-propyl) -amide. 70. The agent of claim 1, wherein the compound of formula I is 4- (1-methylpropylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid. - Contains (N-ethyl-N-propyl) -amide. 71. The agent of claim 1, wherein the compound of formula I is 4- (propylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid (Nethyl). Contains N-butyl) -amide. 72. The agent of claim 1, wherein the compound of formula I is 4- (propylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid dipentylamide. contain. 73. The agent of claim 1, wherein the compound of formula (I) is 4- (propylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid (Netyl-N). -cyclohexyl) -amide. 40 74. The agent of claim 1 wherein the compound of formula I is 4- (propylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid diisopropylamide. 75. The agent of claim 1, wherein the compound of formula I is 4- (ethylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid (N-). containing ethyl N-propyl) -amide. 76. The agent of claim 1, wherein the compound of Formula I is 4- (ethylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid dipropylamide. 77. The agent of claim 1, wherein the compound of formula I is 4- (ethylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid dibutyl amide. contain. 78. The agent of claim 1 wherein the compound of formula I is 4- (butylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid dipropylamide. 60 79. The agent of claim 1, wherein the compound of formula I is 4- (butylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid dibutylamide. 80. The agent of claim 1, wherein the compound of formula I is 4- (1-methylpropylsulfonyl) -1,2,3-triazole-1 (2,3) carboxylic acid dibutyl. contains amide. 81. An agent according to claim 1, wherein the compound of formula I is 4- (isobutylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid dipropylamide. 82. An agent according to claim 1, wherein the compound of formula I is 4- (isobutylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid dibutylamide. 83. The agent of claim 1, wherein the compound of formula I is 4- (1-methylpropylsulfonyl) -1,2,3-triazole-1 (2,3) carboxylic acid dipropyl. contains amide. 84. The agent of claim 1 wherein the compound of formula I is 4- (1-methylpropylsulfonyl) -1,2,3-triazole-1 (2,3) carboxylic acid diisopropyl. contains amide. 85. The agent of claim 1, wherein the compound of formula I is 4- (butylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid (N, N-butyl). ) -amide. 86. The agent of claim 1 wherein the compound of formula I is 4- (isobutylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid (N-ethyl). Contains N-butyl) -amide. 87. The agent of claim 1, wherein the compound of formula I is 4- (1-methylpropylsulfonyl) -1,2,3-triazole-1 (2,3) carboxylic acid ( Contains N-ethyl-N-butyl) -amide. 88. An agent according to claim 1 wherein the compound of formula I is 4- (ethylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid (N-ethylN). -cyclohexyl) -amide. 89. The agent of claim 1, wherein the compound of formula I is 4- (isopropylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid butylamide. 90. The agent of claim 1 wherein the compound of formula I is 4- (isopropylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid dipropylamide. 91. The agent of claim 1, wherein the compound of formula I is 4- (butylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid (Netyl-N). -cyclohexyl) -amide. 92. The agent of claim 1, wherein the compound of formula I is 4- (1-methylpropylsulfonyl) -1,2,3-triazole-1 (2,3) carboxylic acid (N). -ethyl-N-cyclohexyl) -amide. 93. The agent of claim 1, wherein the compound of formula I is 4-propylsulfonyl-1,2,3-triazole-1 (2,3) -carboxylic acid diisobutylamide. 94. The agent of claim 1, wherein the compound of formula I is 4- (propylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid dihexylamide. 95. The agent of claim 1, wherein the compound of formula I is 4- (propylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid (Netyl-N). contains benzyl) amide. -221 184,696 96. The agent of claim 1, wherein the compound of formula (I) is 4- (propylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid (Netyl-N). -isopropyl) -amide. 97. The agent of claim 1 wherein the compound of formula I is 4- (propylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid,? -Hexamethylene- containing amide. 98. The agent of claim 1, wherein the compound of formula I is 4- (propylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid N- (2-). containing cyanoethyl) anilide. 99. The agent of claim 1 wherein the compound of formula (I) is 4-propylsulfonyl-1,2,3-triazole-1 (2,3) -carboxylic acid N-methylanilide. . 100. The agent of claim 1 wherein the compound of formula I is 4- (ethylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid (N-ethylN). -butyl) -amide. 101. The agent of claim 1 wherein the compound of formula I is 4- (isopropylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid (N-ethyl). Contains N-butyl) -amide. 102. The agent of claim 1, wherein the compound of formula I is 4- (isobutylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid (N-ethyl). Contains N-cyclohexyl) -amide. 103. The agent of claim 1, wherein the compound of formula I is 4- (butylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid (Netyl-N). -isopropyl) -amide. 104. The agent of claim 1 wherein the compound of formula I is 4- (isobutylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid (N-ethyl). Contains N-isopropyl) amide. 105. The agent of claim 1 wherein the compound of formula I is 4- (propylsulfinyl) -1,2,3-triazole-1 (2,3) -carboxylic acid diethylamide. 106. The agent of claim 1, wherein the compound of formula I is 4- (propylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid bis (2-chloro) ethyl) amide. 107. The agent of claim 1, wherein the compound of formula (I) is 4- (butylsulfonyl) -1,3,3-triazole-1 (2,3) -carboxylic acid (Netyl-N). contains benzyl) amide. 108. The agent of claim 1 wherein the compound of formula I is 4- (1-methylpropylsulfonyl) -1,2,3-triazole-1 (2,3) carboxylic acid ( Contains N-ethyl-N-benzyl) -amide. 109. The agent of claim 1 wherein the compound of formula I is 4- (isobutylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid (N-ethyl). Contains N-benzyl) -amide. 110. The agent of claim 1 wherein the compound of formula (I) is 4- (methylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid (Netyl-N). -butyl) -amide. An agent according to claim 1 wherein the compound of formula I is 4- (ethylthio) -5-methyl-1,2,3-triazole-1 (2,3) - contains carboxylic acid dimethylamide. 112. The agent of claim 1 wherein the compound of formula I is 4- (propylsulfonyl) -5-methyl-1,2,3-triazole-1 (2,3) carboxylic acid dipropyl. contains amide. 113. The agent of claim 1 wherein the compound of formula I is 4- (propylsulfonyl) -5-methyl-1,2,3-triazole-1 (2,3) carboxylic acid ( Contains N-ethyl-N-isopropyl) -amide. 114. The agent of claim 1 wherein the compound of formula I is 4- (2-propynylthio) -5-methyl-1,2,3-triazole-1 (2,3) carboxylic acid. contains dimethyl amide. 115. The agent of claim 1 wherein the compound of formula (I) is 4- (methylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid (Netyl-N). -isopropyl) -amide. 116. The agent of claim 1 wherein the compound of formula I is 4- (ethylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid (N-ethylN). -isopropyl) -amide. 117. The agent of claim 1, wherein the compound of formula (I) is 4- (methylpropylsulfonyl) -1,2,3-triazole-1 (2,3) carboxylic acid (N-). ethyl-N-isopropyl) -amide. 118. The agent of claim 1, wherein the compound of formula I is 4- (ethylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid diisopropylamide. 119. The agent of claim 1, wherein the compound of formula I is 4- (isobutylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid diisopropylamide. 120. The agent of claim 1, which is as a compound of formula (I) Contains 4- (butylsulfonyl) -1,2,3-triazole-1 (2,3) -carboxylic acid diisopropylamide. 121. The agent of claim 1, which is as a compound of formula (I) Contains 5-methyl-4- (propylsulfonyl) -1,2,3-triazole-1 (2,3) carboxylic acid diisopropylamide. 122. The agent of claim 1 wherein the compound of formula I is 4- (allylthio) -5-methyl-1,2,3-triazole-1 (2,3) -carboxylic acid dimethyl-. containing amide. 123. The agent of claim 1, wherein the compound of formula I is 4- (2-cyanoethylthio) -5-methyl-1,2,3-triazole-1 (2,3). ) containing carboxylic acid dimethylamide. 124. The agent of claim 1, which is a compound of formula (I) Contains 4- (methylthio) -5-propyl-1,2,3-triazole-1 (2,3) -carboxylic acid dimethylamide. 125. An embodiment of the agent of claim 1, which is as a compound of formula (I) Contains 5-ethyl-4- (methylthio) -1,2,3-triazole-1 (2,3) -carboxylic acid dimethylamide. 126. The agent of claim 1, wherein the compound of formula I is 5-isopropyl-4- (methylthio) -1,2,3-triazol-1 (2,3) carboxylic acid dimethyl. contains amide. 127. The agent of claim 1, wherein the compound of formula I is 5- (tert-butyl) -4- (methylthio) -1,2,3-triazole-1 (2,3). ) containing carboxylic acid dimethylamide. -231 184,696 128. A process for preparing 1,2,3-triazolecarboxylic acid amide derivatives of formula (I) wherein R 1 is C 1-8 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, or phenyl (C 1-3) alkyl. )-group; g R ₂ is hydrogen or C 1-8 alkyl; R ₃ is hydrogen, C 1 -C 10 alkyl, halo-C 1 -C 4 alkyl, or C 2 -C 6 alkenyl; R 1 is C 1 -C 10 alkyl, C 2 -C 6 alkenyl, C 3 -C 8 cycloalkyl, halo (C 1 -C 4) alkyl, phenyl (C 1 -C 3) alkyl, or optionally halogen or C 1 -C 4 alkyl is a monosubstituted phenyl; or R ₃ and R 4 together represent a C 3 -C 6 alkylene chain optionally interrupted by an oxygen atom and n is 0, 1 or 2 - and isomeric mixtures thereof, characterized in that one of the compounds of formula (II) , A 3-triazole derivative in the presence of an acid acceptor, with a carbamoyl halide of formula (IH) or optionally in the presence of a catalyst, preferably an organic base, of an isocyanate of formula (IV), R ₂ , R ₂ , R ₃ , R ₄ and S X is halogen, preferably chlorine.