CS270350B1

CS270350B1 - 1-/4-/3-alkoxy-3-alkyl-2-halogenbutoxy/phenyl/alkylester-3/2,2-di halogenethenyl/-2,2-dimethylcyclopropancarboxyl acids as biologically active substance and method of its preparation

Info

Publication number: CS270350B1
Application number: CS884200A
Authority: CS
Inventors: Jitka Ing Csc Kahovcova
Original assignee: Kahovcova Jitka
Priority date: 1988-06-16
Filing date: 1988-06-16
Publication date: 1990-06-13
Also published as: CS420088A1

Abstract

Předmětem řešeni je nová biologicky účinná látka obecného vzorce I, kde symbol R znáči alkylskupinu s rovným či rozvětveným řetězcem s maximálně 4 atomy uhlíku, symbol X značí halogen /chlor; brom/, symbol R# značí methyl- nebo athylskupinu. Oaji pesticidní účinky byly vyzkoušeny například na hmyzu a roztočích. Dalěi čáeti řeěeni je způeob přípravy látky obecného vzorce I, spočívající v reakci hydroxysloučanlny obecného vzorca XI kde symbol R, R1, X mají výše uvedený význam s organickou kyselinou obecného vzorce III, kde symbol X má výše uvedený význam za přítomnosti katalytického množství 4-dimethylaminopyridinu a ekvimolárního množství dicyklohexylkarbodiimidu při teplotě 10 až 20 °C nebo s chloridem či anhydridem organické kyseliny za přítomnosti ekvimolárního množství bezvodého pyridinu při 20 až 60 °C.The subject of the solution is new biologically the active ingredient of the formula I wherein the symbol R is a straight or branched alkyl group with a chain of up to 4 atoms carbon, X is halogen / chloro; bromo, R # is methyl or methyl. Oaji pesticidal effects have been tried for example on insects and mites. Another part of the solution is the method of preparation of the substance of the formula I in the reaction the hydroxylsilyl of formula XI wherein R, R 1, X are as defined above with an organic acid of the formula III, wherein X is as defined above in the presence of a catalytic amount 4-dimethylaminopyridine and equimolar amount of dicyclohexylcarbodiimide at temperature 10 to 20 ° C or with chloride or organic acid anhydride in the presence of equimolar amount of anhydrous pyridine at 20-60 ° C.

Description

CS 270-350 B1 1

BACKGROUND OF THE INVENTION The present invention relates to 1 ' 4- [3- (3-alkoxy-3-alkyl-2-halobutoxy) phenyl] alkyl] -3,2,2-dihalogenenthenyl] -2,2-dimethylcyclopropanecarboxylic acid.

The subject of the present invention is 1- [4- (3-alkoxy-3-alkyl-2-halobutoxy) phenyl] 3- (2,2-dlhalo-halo-phenyl) -2,2-dimethyl-cyclopropanecarboxylic acid ester of general formula I '

wherein R represents a straight-chained alkyl group having a maximum of 4 carbon atoms, X represents a halogen (chloro, bromo), R6 represents a methyl or ethyl group.

The process for the preparation of 1- [4- (3-alkoxy-3-alkyl-2-halobut, oxy) phenylalkylsulfonyl] -3- (2,2-dihalogenethyl) -2,2-dimethylcyclopropanecarboxylic acid is characterized in that it does not the hydroxy compound of formula (II) as well as HOCCH (R) - (CH2) -CH2-CH (X) - (R (0) R (R) - CH3 (II), wherein R, R6 and X are as defined above, are reacted; an organic acid of the formula m X-OCH-CH-CH-COOH (III), 2C / CHg / g wherein X is as defined above, in the presence of a catalytic amount of 4-dimethylaminopyridine and an equimolar amount of dlcyclohexylcarbodllmide at room temperature. up to 20 ° C or with an organic kyeelin anhydride in the presence of an aqueous molar amount of anhydrous pyridine at 20 to 80 ° C. In the following, the invention will be described in more detail by way of non-limiting examples. Example 0.2 g (1 mmol) of 3- (2,2-dichloro-phenyl) -2,2-dimethyl-cyclopropanecarboxylic acid, 0.36 g (1.1 mmol) of 1-C4- (3-methoxy-3-methyl-2) -bromobutoxy) phenyl-1-propanol, 0.2 g (1 mmol) of di-cyclohexylcarbodiimide and 0.1 g (0.1 mmol) of Ν, Ν-diethylamirtopyridine were dissolved and stirred in 10 ml of anhydrous diethyl ether at 15 to 20 ° C for 2 hours. After diluting the reaction mixture with ethyl ether and filtering, the ether layer was washed successively with 6% aqueous hydrochloric acid solution and water, dried and evaporated. The residue afforded 0.31 g (68%) of 1- [4- (3-methoxy-3-methyl-2-bromobutoxy) phenypropyl ester] on a column of silica gel (petroleum ether containing up to 20% v / v diethyl ether). IC analysis (CC14.5%) 1727, 1719 (ωC O ester.), 1614 (9 C »C Cj 15), 1516, 1588, 1614 (Qarorn.), 1391, 1379, 1371 (d, CH CHClcm) "1. NMR analysis (13 C, CDCl 3, 200 MHz) 1 9.72 (CH 3 CH 2), 15.96 (CH 3 CH 2 O), 15.08 and 28.40 ((CH 3) 2 C 4), 22.47, 24.62 ((CH 3) 2 C), 27.22 (1 H) (CH 3) 2), 29.20 (CH 3 OH 9), 31.91, 32.15 (OH-OH), 57.45 (CH 3 CH 2 O), 89.01 (CHBr), 89.88 (CH 3 OH), 78.07 (C (CH 3) 2), 77.18 (CHO) , 121.23 (001 ^) ", 124.98 (CH> CCl 2), 189.96 (0.O), 114.69, - 127.97, 133.19, 157.93 (arom.C).

Biological effects have been tested on the Tetranychus urtlcae mite, which has been found to be affected by oogenesis and spirits.

For 1- [4- (3-methoxy-3-methyl-2-bromo-butoxy) -phenyl] -1-propyl-ether 3- (2,2-dichloro-phenyl-2,2-dimethyl-cyclopropanecarboxylic acid (lo concentration 3% v / v acetone) , the application of the beans to the 10 beans was a total of 3 eggs over a period of 98 hours, of which 2 were dead for 7 days. , which have been licked after 7 days.

Claims

DESCRIPTION OF THE INVENTION 1. 3- (2,2-Dihalothenethyl) -2,2-dimethylcyclopropanecarboxylic acid 1- [4- (3-alkoxy-3-alkyl-2-halobutoxy) phenyl ester of Formula I X2C ' CH-CH-CH-COOCH / R / Z5V OCH2CH / X / - / RO / C / R1 / CH3 (I), xc / ch3 / 2 where R is a straight or branched alkyl group of 8 and a maximum of 4 carbon atoms, X is halogen / chlorine, bromine, R 4 denotes methyl, or ethyl as a biologically active substance.

2. A process for the preparation of 1- [4- (3-alkoxy-3-alkyl-2-halobutoxy) phenyl] -3- (2,2-difluoro-phenyl) -2,2-dimethyl-cyclopropanecarboxylic acid ester of general formula (I), characterized in that a hydroxy compound of the formula II HCHCH (R) - (CH2) -O-CH2CH (X) - (R0) C (R1) CH3 (II), wherein R, R1 and X are as defined above, reacts with an organic acid of the formula III Where X is halogen / chlorobromine in the presence of a catalytic amount of 4-dimethylaminopyridine and an equimolar amount of dicyclohexylcarbodiimide at temperature. 10 to 20 ° C, or with an organic acid chloride or anhydride in the presence of an equimolar amount of anhydrous pyridine at 20 to 60 ° C.