SU1512480A3 - Method of producing derivatives of homopropargylamine - Google Patents

Abstract

The invention relates to novel homopropargylamine derivatives of the formula <IMAGE> in which a) R1 stands for a group of the formulae <IMAGE> and R2 stands for hydrogen or a lower alkyl group, where R6 and R7 are identical or different and in each case denote hydrogen, halogen, the trifluoromethyl group, a lower alkyl group or a lower alkoxy group, s stands for an integer from 3 to 5 and X stands for oxygen, sulphur, the -O-CH2- group, the -S-CH2- group, the methylene or an -N-R8- group, where R8 denotes hydrogen or a lower alkyl group, R3 and R4 can be identical or different and in each case stand for hydrogen or a lower alkyl group and R5 stands for hydrogen, an alkyl group, an alkenyl group, a trialkylsilyl group, a dialkylphenylsilyl group or a phenyl group, where phenyl groups and alkyl groups can be substituted by the hydroxy group, a lower alkyl group, a lower alkoxy group, the phenyl group or halogen, or b) R3 forms a -(CH2)u group with R4, where u denotes an integer from 3 to 5, R1 stands for a group of the formulae IIa to IIc and R2 stands for hydrogen or a lower alkyl group and R5 has the above meaning, and their acid addition salts, and also processes for the preparation of these compounds and their acid addition salts and their use.

Description

The invention relates to a method for producing novel homopropylamine derivatives that exhibit fungicidal activity and can be used to combat phytopathogenic fungi.

The aim of the invention is a method for producing new derivatives in a series of propargylamines having fungicidal activity.

Example. 5,5-Dimethyl-3-hexin-1-ol mesylate.

A solution of 5,5-Dimethyl-3-hex-1-ol in dimethylformamide is treated at 0 ° with 1.2 ml of triethylamine. Then, with stirring, drip

0.335 ml of methanesulfonyl chloride. The reaction mixture is stirred for 2 hours at room temperature. The 5,5-dimethyl-3-hexin mesylate thus obtained

cm

3151

-1-ol is used further without isolation.

Target connection

To the resulting reaction mixture, mg K-methyl-1-naphthylmethanamine is added, the reaction mixture is heated overnight at .80 ° C.

Then the solvent is distilled off in vacuo, the residue is distributed in a saturated aqueous solution of NaHCO3 and ethyl acetate, the organic phase is washed, dried and evaporated. The crude product is chromatographed on silica gel toluene / ethyl acetate 9/1 and the desired product is obtained as an oil.

Analogously to Example 1, the following compounds are obtained, listed in Table. one

The resulting compounds are developed. fungicidal activity and can be used in agriculture.

Methods of testing for biological activity.

Liquids containing test compounds in various concentrations are sprayed onto the plants. After dried, the plants are treated with a spore suspension and then incubated for 7 days in an incubation chamber at

humidity 60-100 and 21-30 ° C .. Effek-

The potency of the compounds of the invention at each concentration is determined by comparing the extent of the fungus infestation of an untreated fungicide and a fungus infected control plant. The results obtained at different concentrations allow the EU 90 to be calculated, i.e. the concentration at which a decrease (i.e., 90) in fungal damage is observed by extrapolating the consumption rate / activity curve.

Some of the thus determined values of the EU 90 are presented in Table. 2

Thus, the compounds in accordance with this method show fungicidal activity, while structural analogues of such activity do not show.

Claims (1)

Invention Formula The method of obtaining derivatives of homo propargylamine formula RI R. K2-s: -B- (ch2) where n 2 or 3, R, a group of one of the formulas or 0 five thirty where ri - v S - X R-, r-de p hydrogen, halogen or. C alkyl; an integer from 3 to 5; oxygen, sulfur or -0-СЫ - group; hydrogen or C-Cd-alkl; R and R. are the same or different, and means hydrogen or C - C. alkil or Rj and R (). together they form - (SP2), - a group, an integer from 3 to 5., Rj is hydrogen. C, C, alkyl, Cd - C-cycloalkyl, C - Cg alkenyl-, tri (c-C5-alkyl) silyl-, di- (c, -Cd-alkyl) -phenylsilyl-, phenyl or. phenyl-C-C5 is alkyl, and the phenyl, cycloalkyl and alkyl groups may be substituted with hydroxy or C ;, C-alkoxy or halogen, 0 characterized in that the compound of the formula RI I R2-C-NH-R. where R, - R. have the indicated values, are reacted with a compound of the formula CH, (CHj) „-CSC-R y where R5n have the specified value, followed by isolation of the target product. Table 1 Continuation of table 1 T abo l and c a 2