SU1584736A3 - Redenticide concentrate - Google Patents

Abstract

Compounds of the general formula (I), <IMAGE> (wherein A is oxygen or a valence bond, R<1> is a 1-tetralyl group or a group of the general formula (IV) or (V), <IMAGE> wherein Y stands for tert.-butyl, isobutyl, diphenylmethyl, 4-methyl- diphenylmethyl, 4-chloro-diphenylmethyl or 4-bromo-diphenylmethyl group and Q stands for phenyl, 4-chloro-phenyl or 2-furyl group, with the proviso that if A is a valence bond, R<1> represents a group of the general formula (IV), whereas if A is oxygen, R<1> represents the 1-tetralyl group or a group of the general formula (V), R<2> is hydrogen or a straight-chained or branched C1-22 alkyl or C12-20 alkenyl group, and R<3> and R<4> each stand for a straight-chained or branched C1-22 alkyl or C12-20 alkenyl group, and the total number of carbon atoms contained by the R<2>, R<3> and R<4> groups is more than 12) are rodenticides.

Description

This invention relates to rodent control agents, namely rodenticidal

concentrates containing derivatives of 1,3-indandione.

yellowish brown

lao nD

The purpose of the invention is to increase the stability of the rodenticidal concentrate.

At m-r 1. A mixture of 4.18 g (15.5 mmol) of dimethylhexadecylamine, 5.82 g (15.5 mmol) of chlorfacinone and 20 mp of n-hexane is refluxed for 1 hour during this time. solid chlorofaciline is completely dissolved and a clear orange solution is formed. The solvent is distilled off. The dimethylhexa-decylamine salt of chlorfacinone is obtained in

dense (thick) residue, 1.5731. When cooled, the product does not crystallize, but forms a glassy solid at 32 ° C. Found,%: C 76.53J H 8.52, C1 5.46.

, SSN

Calculated,%: C, 76.43; H 8.45 C1 5.50.

Example 2 A mixture of 2 g (3.82 mmol) of tris (dodecyl) amine and 40 ml of hexane was heated to reflux. Difacinone is added to the mixture. in small portions (approximately 0.1 g) until the last portion at the boiling point does not dissolve. In total, 1.43 g of difacinone is added. The reaction mixture is cooled and allowed to stand for two days to remove excess crystalline difacinone. The crystals are filtered off and washed with a small amount of hexane. The filtrate is combined with the washing liquid and the solvent is distilled off. 0.11 g of unreacted difacinone is removed. 1.32 (3.87 mmol) difacinone are involved in the interaction, this amount is almost equivalent to the amine used.

Tris- (dodecyl) amine salt of difacinone is obtained in the form of a yellowish-brown oil, n ° 1.5348. When cooled, the product does not crystallize, and when it forms a glass

solid solid.

Example 3 A mixture of 1 g (2.67 mmol) of chlorofacinone, 1.14 g (3.2 mmol) of tris (octyl) amine, and 50 ml of acetonitrile is refluxed until the amount of the tris (octyl) amine present as a separate phase no longer decreases and practically does not form.

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clear homogeneous solution. The mixture is cooled to room temperature, the excess Tris (octyl) amine and acetonitrile solution are separated, cooled to -18 ° C. The tris (octyl) amine salt of chlorfacinone precipitates on the walls of the flask as a tan resin. The solvent is removed by decantation, the resinous product is washed twice with 15 ml of acetonitrile (dissolving and cooling) and traces of the solvent from the product are removed under reduced pressure.

Obtain 0.51 g of a gummy substance, p 1.5582. When cooled, the product does not crystallize, but forms a glassy solid at -10 ° C.

Found,%: C 77.87; H 8.81, C1 7.78.

C47H66C1N03

Calculated,%: C 77.81; H 8.76; C1 4.89.

The product is highly soluble in alcohols, acetone, hexane and dichloromethane, even at room temperature. 1 g of chlorofacinone used as starting material at room temperature can be dissolved only in 1000 ml of n-hexane.

EXAMPLE 4 A mixture of 1 g (2.67 mmol) of chlorofacinone, 0.7 g (3.28 mmol) of dimethyldodecylamine and 100 ml of n-hexane is refluxed. The solid chlorofacinone for about 20 minutes completely dissolves and at the same time the desired product is released as a yellowish-brown oil phase. The reaction mixture is cooled and the hexane phase containing excess amine is removed by decantation. 20 ml of hexane is added to the oil product, the mixture is heated to boiling, then allowed to cool and the hexane phase is removed by decantation. These measures are repeated for purification and the obtained desired product, then it is processed under reduced pressure to remove the solvent.

Obtain 0.81 g of dimethyldodecylamine salt of chlorofacinone in the form of a yellowish-brown thick oil, p 1,5858. When cooled, the product does not crystallize, but forms with a glassy solid.

Found,%: C 75.70; H 8.12; C1 5.90.

СТНЧ6СШ) 3

Calculated,%: C 75.55; H 7.68; C1 6.03.

The product is very soluble at room temperature in 1 volume of methanol, acetone or benzene. In contrast. to this, tg of chlorfacinone used as the starting material is dissolved at room temperature in only 1370 ml of methanol, 47 ml of acetone or 8 ml of benzene.

Example 5-8. The compounds listed in Table 1 are obtained by applying the corresponding starting materials in analogy to Examples 1-4.

Example 9. A mixture of (8.8 mmol) difacinone and 3.12 g (8.8 mmol) of tris- (octyl) amine i.h stirring and heating at 110-120 ° C is converted into a homogeneous salt melt.

The product is a yolk, a clear, honey-like substance, the freezing point of which is -389 ° C and the refractive index of which is 1.5558.

Example 10. 2.3 g (0.01 mmol) of valon and 2.13 g (0.01 mmol) of dimethyl dodecylamine are reacted (Example 9) at-12 CMO3 ° C. A viscous melt is obtained, which after cooling is converted into a yellow-brown crystalline mass. After recrystallization with n-hexane, mp. 58-59 ° C.

Example 11. 2.3 g (0.01 mmol) of valon and 5.22 (0.01 mmol) of tris (dodecyl) amine are reacted. The reaction starts at room temperature, after which it is raised to .. A yellow-brown oily liquid is obtained, which solidifies into a glassy substance. Point of solidification from (-40) to (-44) ° C. The refractive index is p 1,5002.

Example 12. A mixture of 1 mmol valon and 1 mmol tris (octyl) amine is stirred at 120-130 ° C until a homogeneous melt is formed.

After cooling the melt to room temperature, a brown-red oily product is obtained. The solidification point is -15 ° C. The refractive index of p, 1.5192.

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To obtain a rodenticide concentrate, the active compound, prepared according to examples 1-12, is mixed with an appropriate solvent.

Table 2 presents examples of compositions.

Data on the biological activity of the proposed compounds obtained on. laboratory white rats to which a 0.25% oily solution of the active is administered through a stomach tube. compounds.

The lethal doses of the active compound (LD5o) are given in Table 3.

Data on the lethal dose (LDsa) of ready-to-use, tris-dodecylamine salts containing baits are given in table 4. The baits tested contain 0.25% active compound, which is applied as an oily solution to the surface of the corn.

Compositions 1-18 are subjected to a storage stability test. Samples incubated at 10.25 and 40 ° C.

In no case does the precipitate fall out within 2 years. For comparison, 7-95% solutions of chlorofacinone-amino salts in petrolatum oil (indal, tributylamine, quinoline, and cyclohexylamine salt of chlorphacinone) are used. These concentrates are unstable, contain sediment

Claims (1)

Formula invented and Rodenticide concentrate containing derivatives of 1,3-indanedione as an active compound and a solvent, characterized in that, in order to increase the stability of the concentrate, it contains derivatives of the general formula as 1,3-indanedione derivatives ./ .RI NtR3 where R, - C-Y; if Y is 4-chlorodiphenylmethyl group, then Rg is a tridecyl group and R4 is HJ  in a ratio of 3: 2: 1, a mixture of boiling with glycerol trioleate in a ratio of 1: 1, a mixture of peanut oil with benzene in a ratio of 3: 1, a mixture of glycol with dimethyl sulfoxide in a ratio of 1: 1, a mixture of paraffin oil and cyclohexane in the ratio of 9: 1, sunflower, olive spindle, paraffin, flax, peanut and vaseline oils, glycol, dimethyl sulfoxide, oleic acid, glycerol trioleate, benzene or trisdodecylamine in the following ratio of components, wt.%: a metal group and a C dodecyl or hexadecyl group; Ri-R4 is octyl or dodecyl, Group; if Y is a diphenylmethyl group, then Rg and R3 - methyl group and R / J - dodecyl or hexadecyl Q Group; .-R4, - octyl or dodecyl group, if Y is isobutyl, then RQ and R - methyl group-) 5 naj R - dodecylna | group; Derivatives   to, g, - € zylna or octyl 1,3-indandion 7-95 the group indicated as a solvent is that it contains a substance selected from the group: Specified rast-opptchtttt, the rest olive oil or oleic acid tT a b l and c a 1 Example Starting material Color Consistency Temperature  freezing, and I: with one. 5 Chlorfacinone bis- (tridecyl) amine Zheltovato- Smola1,5445 -10 brown 6.--tris- (dodecyl) amine Orange- Oil1.5420 +7 is yellow 7Difacinone Dimethyldodecylamine Brown - - 1,5800 -27 8- - Dimethylhexadecium- Dark co- - - 1,5648 -14 lamine brown Note. Example 5 is carried out analogously to example 4, and examples 6-8 - analogously to example 1. Table 2 "G Composite Components Contents, g 123 in a ratio of 3: 2: 1, a mixture of boiling with glycerol trioleate in a ratio of 1: 1, a mixture of peanut oil with benzene in a ratio of 3: 1, a mixture of glycol with dimethyl sulfoxide in a ratio of 1: 1, a mixture of paraffin oil and cyclohexane in a ratio of 9: 1, sunflower, olive, spindle, paraffin, flax, peanut and vaseline oils, glycol, dimethyl sulfoxide, oleic acid, glycerol trioleate, benzene or trisdodecylamine in the following ratio of components, wt.%: 1 Chlorfacinone bis-tridecylamine salt80 Sunflower oil920 2Chlorfacinone-dimethyldodecylamine salt100 Olive oil900 3Chlorfacinone-dimethylhexadecylamine salt 150 Spindle oil850 4 Chlorfacinone-tris-octylamine salt200 Paraffin oil800 5 Chlorfacinone-tris-dodecylamine salt250 Linen maslo750 P 158473612 Table4 Chlorfacinonova salt 40-50 Difacinonov 40-45 Valonova SolM 50 330-360 380-420 43-50