2,2-dimethyl-1,3-propylene glycol ether- phenylaminomethylphenol acid with nematocidal activity


(57) Abstract:

Usage: in agriculture as nematocide drugs. The inventive product - 2,2-dimethyl-1,3-propylene glycol ether of a-phenylaminomethylphenol acid f-ly C18H22NO2PS, output to 78.3% , so pl. 108 - 109 C. Reagent 1: Reagent 2: C6H5CH=NC6H5. Reaction conditions: in an environment of absolute ethanol in the presence of catalytic amounts of concentrated hydrochloric acid at boiling.

The invention relates to the chemistry of organophosphorus compounds, namely, a previously undescribed 2,2-dimethyl-1,3-impregnated - longicollum air-phenylaminomethylphenol acid of the formula I

/ manifesting nematocidal activity.

To combat nematodes living in the soil, used drugs such as 1,2-dichloropropane, 1,2-dibromethane, 2,3-dibromo-1-chloropropane(nemagon) with low nematocidal activity and moderately toxic to warm-blooded. Drugs such as S-propyl-0-phenyl-0-ethylphosphate(heteropus), 0-(1-isopropyl-5 - chlor,2,4-triazolyl-3)-diethylthiophosphate(isazofos), N-isopropylamino-0-(3-methyl-4-methylthiophenyl)-0-ethylphosphate(fenamiphos), are effective nematicides with nd50rats is 5-60 mg/kg is Often used in practice nematocidal drug - 0,0-diethyl-0-(2,4-dichlorophenyl)infostat (VC-13) - less toxic to warm-blooded animals (LD50for rats 270-300 mg/kg), but it is inferior to the above derived phosphoric and infostroy acids on nematocidal activity: the rate of flow of vc-13 is 180 kg/ha

The aim of the invention is to reduce the toxicity to warm-blooded animals the drugs used to fight against round worms, while maintaining high nematocidal activity.

This goal is achieved by obtaining a new chemical compound is 2,2-dimethyl-1,3-propylene glycol ether - phenylaminomethylphenol acid of formula 1.

A method of obtaining compound 1 is that benzylideneaniline subjected to interaction with 2,2-dimethyl-1,3-propertyofferform in absolute ethanol in the presence of catalytic amounts of concentrated hydrochloric acid.

2,2-Dimethyl-1,3-propylene glycol ether-phenylaminomethylphenol acid is a crystalline substance of a yellowish color, soluble in most organic solvents. His Stroitelnye can be illustrated by the following example obtain 2,2-dimethyl-1,3-propylene glycol ether-phenylaminomethylphenol acid.

P R I m e R 1. To 3,62 g (0.02 mol) benzylideneaniline in 30 ml of absolute ethanol is added 3,30 g (0.02 mol) of 2,2-dimethyl-1,3-proponentificate, 3-4 drops of conc. hydrochloric acid and the reaction mixture is heated in an air bath at a low boiling solvent for 1.5 h, after which it is cooled and placed in the fridge. The next day rolled crystals, is filtered off, dried, recrystallized from ethanol. Output to 78.3% (from Teoret. ), 5,42, So pl. 108-109aboutC. Rf 0,351 upon elution with benzene.

IR spectrum (liquid paraffin, KBr, , cm-1): 3380 (NH), 1030 (PO-C), 935 (dioxaphospholane cycle, OS-O).P108.50 M. D. Mass spectrum: M+m/z 347 (5,18)% ).

Found, % : C 62,02, 62,11; H Between 6.08, Of 6.02; N 4,12, 4,21; P 8,80, 8,82; S 9.28 Are, 9,34.


Calculated, % : C 62,24; H 6,34; N Is 4.03; P 8,93; S Which 9.22.

Tests nematocidal activity 2,2-dimethyl-1,3-propylene glycol ether-phenylaminomethylphenol acid was conducted in the Central Asian scientific research Institute of Phytopathology. Below is the methodology of the study.

Studies were performed in laboratory conditions. The test objects were adult nematodes Aphelenchus avenae, Aphelenchoides besseyi. Were used for comparison industry is usaamah substances. After a day spent considering the death of nematodes in comparison with the control (placed in water) nematodes.

It was established that the test compound is 2,2-dimethyl-1,3-propylene glycol ether-phenyliminomethyl - infostroy acid in a concentration of 0.01% has in respect of Aphelenchus avenae, Aphelenchoides besseeyi nematocidal activity level benchmark-heteropoda, causing 100% mortality of species of nematodes. At the same time a new connection has a significant advantage compared to the benchmark, as it is less toxic to warm-blooded: it LD501200 mg/kg for white mice. LD50heterophase for mice 30-60 mg/kg (56) Melnikov N. N. Chemistry and technology of pesticides. M. : Chemistry, 1974, S. 51-53.

Melnikov N. N. and other Chemical means of plant protection. Handbook, M. : Chemistry, 1980, S. 143, 159, 201.

Shamshurin A. A. and other Physico-chemical properties of organic pesticides and growth regulators. Handbook, M. : Nauka, 1966, S. 77.

2,2-Dimethyl-1,3-propylene glycol ether-phenylaminomethylphenol acid formula

< / BR>
with nematocidal activity.


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16 cl, 10 tbl, 87 ex

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2 tbl, 10 ex

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64 cl, 5 tbl, 38 ex

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34 cl, 19 ex

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4 ex

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1 tbl, 3 ex

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26 cl, 1 ex

FIELD: chemistry.

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184 cl, 52 tbl, 62 ex

FIELD: chemistry.

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18 ex, 1 tbl

FIELD: medicine; pharmacology.

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46 cl, 1 tbl, 233 ex

FIELD: chemistry.

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14 cl, 12 ex, 1 tbl

FIELD: chemistry.

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or ,

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13 cl, 30 ex, 2 tbl