SU925248A3 - Process for producing 3-substituted carbonylaminophenyl esters of n-(2-propinyl)-carbanilic acid - Google Patents

Abstract

Novel compounds of the general formula I <IMAGE> (wherein R represents C1-C4-alkyl, C3-C4-alkenyl or C3-C4-alkynyl and X represents O or S) and their manufacture. The compounds have a herbicidal action, especially a selective herbicidal action, and accordingly may be made up with suitable carriers into herbicidal preparations and may be used for protecting living plants and crop areas against weeds.

Description

subjected to interaction with M- (2tpropinyl) -aniline. The process is carried out in the presence of potassium carbonate, which acts as an acid acceptor when in an ethyl acetate medium.

Example M-methoxycarbonylaminophenyl ester of M- (2-propynyl) carbanilic acid.

8 solution of 39, g (0.3 mol) of N- (2-propinyl) -aniline in 75 ml of ethyl acetate with stirring and cooling; a solution in 68.7 g (0.3 mol) of 3-methoxycarbonyl-aminophenyl chloroformate ester is added dropwise in 150 ml of ethyl acetate and at the same time a solution of 41.4 g (0.3 mol of potassium carbonate in 150 ml of water) is added dropwise. The mixture is stirred for 30 minutes at, then the organic phase is separated and, added ice, washed with dilute hydrochloric acid and After drying with magnesium sulfate under reduced pressure, evaporate and mix with 500 ml of isopropyl ether, of which the reaction product crystallized. Yield b7,9 g (69.3 by calculation). mp. 104C.

Similarly, new compounds are obtained, presented in: Table 1.

Table 1

3- (Methylthiocarbonylaminophenyl ester of M- (2-propynyl) -carbanilic acid

3- (Ethylthiocarbonylamino) -phenyl ester of H- (2-propynyl) -carbanilic acid

3- (2-propynilox | 1carbonylamino) phenyl ester of M- (2-propynyl) -carbanilic acid

3- (Methylpropoxycarbonylamino) phenyl ester of M- (2-propynyl) -carbanilic acid

3- (1-Methylethoxycarbonylamino) phenyl ester of M- (2-propynyl) carbanilic acid

3- (1-Methyl-2-propenyloxycarbonylamino) -phenyl ester of M- (2-propynyl) -carbanilic acid

3- (Ethoxycarbonylamino) -phenyl ester of H- (2-propynyl) -carbanilic acid

The structure of the obtained compounds was confirmed by elemental analysis and IR spectroscopy.

The compounds obtained are soluble in isophorone, cyclohexanone, acetone, tetrahydrofuran, dimethylformamide, dimethyl sulfoxide, and other solutions.

99

118

101-103 76-79

96-97

solvent, but poorly soluble in water, benzene and toluene.

Example 2 In a greenhouse, plants are sprayed in the post-emergence period with the compounds in the table in the form of aqueous emulsions or suspensions in a dose of 5 kg of active

59252 86

500 on the O-1, 2, 3 scheme, (O - no

substance tar. .

Three weeks after the treatment, the destruction is usually achieved; the results are monitored by scoring 5 decays (Table 2).

PRI me R 3. The plants in the table are sprayed evenly. in the post-emergence period in the greenhouse with the compound (and the known compound in the form of an aqueous emulsion in an amount of 1 kg of the active substance per hectare,

Three weeks after treatment, the results are evaluated on a scale from

Proposed

3- Ethoxycarone6-N-phenophenyl ester of H- (2-propynyl) 10-carboxylic acid

3-methoxycarbonylaminophem-N- (J -stilphenyl) carbamate, I

The novel compounds exhibit a more selective action in comparison; - destruction of plants).

The results show that both

table 2

, O to 10 (o - complete destruction; 10 - no damage).

The compound has an increased selective herbicidal action, and the known compound does not.

(table 3). I

Table 3

Known

Claims (2)

with known structural analogs of the same action. The proposed compounds can be used against such resistant weeds and secondary flora, with which we cannot successfully combat the herbicides known in practice from their acquired resistance. The novel compounds are characterized by a broad herbicidal action on the leaves. They can be used against dicotyledon weeds. In the post-emergence period, these compounds can be borne with such fields as Stellaria media, cyber, ric ric,, ric ric,, a a,, ric a a, ric, a a a ics ics,, ics ics ics, ics ics,, ics ics, ics ics a ics ics a ics ics a a ics ics a ics ics a a a a a a a a a a a a a a a as propagating seeds, weeds typically use from 1 to 5 kg of active substance per hectare. At the same time, the active substances of lro are a selective effect in cultures of such useful plants as cotton, potato, corn, wheat and rice. Claims for the preparation of 3 substituted carbonylaminophenyl esters of N- (2-npo 9 8 penyl) -carbanilic acid of the general formula I O - Co-C- -eng- d "CH - {- XR O where R is alkyl or methylpropenyl, or propinyl; oxygen or sulfur in order. the compound of the general Formula II 0-COC 1 o, is reacted with N- (2-nopinyl) aniline in the presence of KjCO, 8-G 2 ° C. in ethyl acetate at Sources of information taken into account in the examination 1. German patent number 1567115, cl. A 01 N 17/10, published. 1972. 2. Vorozhtsov N. N. Basics of the synthesis of intermediate products and dyes. M., GNTI chemical literature, 1955, p. 528-530.