-cyano-3-phenoxybenzyl 1r, 3s - 2,2-dimethyl-3-(2 - chloropropene-1-yl)-cyclopropanecarboxylic in the form of a mixture of isomers exhibiting insect-acaricide and larvicidal activity

 

(57) Abstract:

Usage: in agriculture, as the product exhibits insecticidal activity. Essence: new product - a cyano 3-phenoxybenzyl IR, 3S-2,2-dimethyl-3-/2-chlorpropyl/cyclopropanecarboxylate General formula I in the form of a mixture of isomers . The product is isolated in the form of a yellow viscous oil, the ratio of the isomers is Ia 1, IB 4-2. Acaricidal activity of the obtained product is 0.23+0.02 μg/kg Insecticidal activity of 0.28 µg/g in relation to the imago meadow moth. table 1.

The invention relates to new chemical product, particularly to-cyano-3-phenoxybenzyl 1R,3S-2,2-dimethyl-3(2-chlorpro - pen-1 - yl)-cyclopropanecarboxylate formula I

in the form of indivisible mixture of isomers Ia and IB in the ratio from 1:2 to 1:4.

Product (I) belonging to the group of a PYRETHROID insecticide, shows the following types of biological activity:

acaricidal activity against adults of the taiga tick Ixodes persulcatus P. Sch - vector of tick-borne encephalitis virus;

insecticidal activity against adult meadow moth - one of the most dangerous pests of cultivated plants of Siberia;

larvicidal activity against larvae asanoha composition, possessing high biological activity derived from known acid (II):

< / BR>
The product I shows high biological activity greater than the activity of the analogs, which is confirmed by the data shown in the example:

P R I m m e R. To a solution of 11.3 g of the acid (III) in 50 ml of benzene was added 4.3 ml of chloride tiomila and leave the mixture overnight at room temperature. The benzene and excess chloride tiomila distilled off in a water jet vacuum pump, to the residue with stirring and cooling in an ice bath is added dropwise a solution of 12 g of cyanhydrin m-phenoxybenzaldehyde and 9 ml of pyridine in 20 ml of benzene. The mixture is stirred for one hour, add 100 ml of water and 100 ml of pentane, stirred and extracted with pyridine solution of 5 ml of hydrochloric acid (conc.) in 20 ml of water, the organic layer is separated, washed with 50 ml of 0.5 n sodium carbonate solution, dried with calcium chloride and after evaporation of the solvent gain of 21.5 g of brown oil. The crude product will permalert on silica gel (eluent - pentane-benzene). After evaporation of the eluate produce 14 g (59%) ether (I) in the form of a yellow viscous oil, which according to NMR data1H and NMR13From the comparison with the spectra of the isomers [1] shows the presence of only wear for white mice).

The synthesized compound was tested for acaricidal activity against adults of the taiga tick Ixodes persulcatus. The tests were carried out in may 1991 under laboratory conditions using female ticks from the natural population (in the vicinity of lake Teletskoye, Gorno-Altai ed. region), determining the value LD50the method of topical application. For comparison used high-performance commercially available PYRETHROID insecticides. The results are given in table. 1.

Testing insecticidal activity of compound I against the caterpillars of the meadow moth Loxostege sticticalis (Pyralidae) was conducted in April-may 1990 at the Institute of Cytology and genetics of SB as USSR. In experiments were used caterpillars older weighing 30-45 mg, obtained from butterflies laboratory setting. Insecticidal activity was estimated by the value of LD50the method of topical application. As the standard used highly effective drugs from the group of pyrethroids. Test data are given in table. 2.

Tests larvicidal activity of compound (I) against the larvae of the green meat flies Lucilia senicata Mg. (Calliphoridae) was performed in August 1990 in the Altai experimental use is acii. Insecticidal efficacy was determined by the time SD100methods of topical application of (T) and contact dispensing (K). As standards were used to highly active drugs from the group of pyrethroids. Test data are given in table. 3.

The test results of samples with the ratio of the isomers Ia and IB from 1:2 to 1: 4 differ slightly from those shown and are within experimental error.

-Cyano-3-phenoxybenzyl 1R, 3S-2,2-dimethyl-3(2-chloropropene-1-yl)-cyclopropanecarboxylic General formula

< / BR>
where

R - C = (Ia);

R-C = (IB)

in the form of a mixture of isomers Ia and IB at a ratio of 1 : 2 to 1 : 4, exhibiting insect-acaricide and larvicidal activity.

 

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