UA34258C2 - 5-(4-метhylphenyl)-4-phenyl-1,2,4-тriazol-3-thioether of 2,4-dichlorophenoxyacetic acid as a herbicide - Google Patents

Abstract

The invention relates to a herbicide - a new chemical compound, which according to the structure thereof is close to structures, which have shown themselves in controlling weeds of mono- and dicotyledonous species, and are 5-(4-methylphenyl)-4-phenyl-1,2,4-triazole-3-thioether of 2,4-dichlorophenolacetic acid. It allows to carry out an effective control over wild grown narcotic-bearing plants of the Papaveraceae family and hemp.

Description

Description of the invention

The invention relates to the field of organic chemistry, specifically to the new compound 2 5-(4-methylphenyl)-4-phenyl-1,2,4-triazol-3-thio)ether of 2,4-dichlorophenoxyacetic acid of formula (1):

And ich y tsui or still uk zsosno ki to sne which is highly effective in the fight against monocotyledonous and dicotyledonous weeds and can be used as a herbicide in agriculture.

It is known to use 2,4-D (1), which is closest to the proposed compound (I) 75 in terms of chemical structure, as a herbicide. 2,4-D is accepted by us as a base compound.

The common features of the proposed compound (I) and the herbicide 2,4-D are that they belong to the same class of chemical compounds - derivatives of 2,4-dichlorophenoxyacetic acid, have herbicide properties and belong to low-toxic compounds.

Distinguishing features:

The proposed compound (I) is a complex ester, which includes fragments of 2,4-dichlorophenoxyacetic acid and substituted 1,2,4-triazolethiol.

The basic compound 2,4-D is chemically 2,4-dichlorophenoxyacetic acid.

The proposed compound (I) is less toxic to warm-blooded animals than 2,4-D.

The proposed compound (I) acts on monocotyledonous and dicotyledonous types of weeds, unlike 2,4-D, which is effective only against dicotyledonous plants.

The task of the invention is to create a new herbicide -5-(4-methylphenyl)-4-phenyl-1,2,4-triazol-3-thio) about 2,4-dichloro-phenoxyacetic acid ester, which would have higher phytotoxicity and be less more toxic to warm-blooded animals than the base compound 2,4-D.

The task of the invention is achieved by the synthesis of 5-(4-methylphenyl)-4-phenyl-1,2,4-triazole-3-thio)ether with 2,4-dichlorophenoxyacetic acid, which is a highly effective herbicide for combating monocotyledonous and dicotyledonous weeds and has much greater activity than the known herbicide 2,4-D. at

The synthesis of a new compound of the general formula (I) is carried out by the reaction of 2,4-dichlorophenoxyacetic acid chloride and the sodium salts of 4,5-diarm-1,2,4-triazole and od and b-3.

The invention is illustrated by the following examples. WITH

Example 1. Synthesis of 5-(4-methylphenyl)-4-phenyl-1,2,4-triazole-3-thio)ester 2,4-dichlorophenoxyacetic acid se (compound 1).

A mixture of equimolar amounts of 2,4-dichlorophenoxyacetic anhydride and sodium salts of 4,5-diaryl-1,2,4-triazolthiols-3 in a benzene solution is heated with intensive stirring in a reactor with an inverted refrigerator for 20-30 minutes. After cooling the mixture, the sodium chloride precipitate is separated, the remaining benzene is evaporated in the vacuum of a water jet pump. - c The residue crystallizes, it is filtered, washed with benzene and dried. Thus, 5-(4-methylphenyl)-4-phenyl-1,2,4-triazole-3-thio)ester of 2,4-dichlorophenoxyacetic acid "" (compound 1) was obtained.

Heat temperature 192-470. Calculated from 6.7690.

С2озН4и7С12М30». Found 890. so White crystalline powder, odorless. Well soluble in dimethylsulfoxide, slightly soluble in acetone, water. Compound (I) is well stored at a temperature of 207"C. Aqueous solutions of compound (I) retain their herbicidal properties for at least 30 days. Example 2. Vegetative studies of the herbicidal activity of 5-(4-methylphenyl)-4-phenyl- 1,2,4-triazol-Z3-thio) ester of 2,4-dichlorophenoxyacetic acid (compound 1). ii Plants of barley "Odessky-100" and radish of the oil variety "Raduga" were germinated in vegetative conditions on a mixture of soil: sand in a ratio of 1:1. pH (KSI) 5.9 (21, humus content 1.596 21.

The activity of the compounds was studied during pre- and post-emergence application.

For pre-emergent use, the required amount of compound (I) was first dissolved in dimethylsulfoxide (HDMSO), and then brought to 50 ml with distilled water (the final concentration of DMSO is no more than 195). Compounds were introduced in a volume of 5 Oml of solvent per vessel. iF) During post-emergence application, the above-ground parts of 7-day-old plant seedlings were immersed in aqueous solutions of the compounds under study (final concentration of DMSO no more than 1905) for 5 minutes at 2076. The degree of inhibition of plants was determined visually in comparison with the control: 10095 - control plants without the use of drugs, 090 - complete death of plants in experiments with herbicides. Repetition - b-fold.

The results of the experiments were statistically processed according to Dospekhov |ZI. 65 Study of herbicidal activity of 5-(4-methylphenyl)-4-phenyl-1,2,4-triazol-3-thio) ester of 2,4-dichlorophenoxyacetic acid (I) and basic compound 2,4-D. -D-

Pa and Mon Ma 07700000 66 May 00000006 and My 00000006 Vom 00111106 Mom 11711001 Zda 0000016 7 of 25 Notes. Variants that do not differ at the 0.05 level of significance are marked with the same letters. at

As evidenced by the data shown in Table 2, the proposed compound (I) in doses of kg/ha and above completely inhibits the growth of monocotyledonous and dicotyledonous plant species. In a dose of 0.1 and 0.01 kg/ha, compound (I) suppresses mainly dicot species.

DMSO applied as a solvent had no phytotoxic effect.

The proposed compound (I) is significantly superior in activity to 2,4-D when used on a ladder. со 30 The proposed compound (I) is also effective when applied to seedlings, unlike 2,4-D, which is known exclusively as a post-emergence herbicide.

Example 3. Study of the acute toxicity of the compound (I) (5-(4-methylphenyl)-4-phenyl-1,2,4-triazole-3-thio) ester of 2,4-dichlorophenoxyacetic acid). hE

The toxicity of compound (I) was studied in acute experiments using the standard method |4| on white male mice and 32 female mice weighing 18-20 g by oral administration of aqueous solutions. Animal subjects were observed for 24 hours. The toxicity indicator is the value of LdD»o (the dose that causes the death of 50,956 experimental animals, in mg/kg of mass). Statistical processing was carried out according to the Litchfield method and

Wilcoxon in the Roth modification |4|. "

The calculated LDv»o value of compound (I) exceeded 400 Ω/kg. Z7Z

It was established that the toxicity of the proposed compound (I) for animals is significantly lower than that of the prototype 2,4-D - with 350-BbOMH/Kkg. ; from" Literature. 1. Melnikov N.N., Novozhilov K.V., Belan R.O. and others. Handbook of pesticides.-M.: Khimiya, 1985.-352p. 2. Radov A.S., Pustovoi I.V., Korolkov A.V. Workshop on agrochemistry.-M.: Agropromizdat, 1985.-3126.

Z. Dospekhov B.A. Methodology of field opiate.-M.: Agropromizdat, 1985.-351p. at 4. Belenky M.L. Damn it! Quantitative assessment of pharmacological effect.-L.: Medgiz, 1963.-95p.

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Claims (1)

The formula of the invention with 50 so 5-(4-methylphenyl)-4-phenyl-1,2,4-triazole-3-thioester of 2,4-dichlorophenoxyacetic acid of the formula (I) -yesosno (and ra ' o M 60 SeNe as a herbicide. Official bulletin "Industrial Property". Book 1 "Inventions, useful models, topographies of integrated V5 microcircuits", 2003, M 11, 11/15/2003. State Department of Intellectual Property of the Ministry of Education and Science of Ukraine.