Method of producing deriavives of 2-cyano-2-phenylacetic acid

专利摘要:
The invention relates to new plant growth regulating compositions, which contain as active agent 0.001 to 95% by weight of one or more compound(s) of the general formula (I), <IMAGE> (I) wherein R1 and R2 each represent hydrogen atom, a C1-5 alkyl group, a C5-7 cycloalkyl group, an aryl group, a halogen-substituted aryl group, an aralkyl group, a C2-5 alkenyl group or a C2-5 alkynyl group, or R1 and R2 form, together with the adjacent nitrogen atom, a morpholino, pyrrolidino, piperidino or perhydroazepinyl group, and R3 stands for hydrogen or a C1-5 alkyl group, together with an inert, solid, liquid and/or gaseous carrier or diluent, and optionally one or more additives, such as surfactants or other substances of plant biological activity. The compounds of the general formula (I) in which R1 is hydrogen and R2 stands for hydrogen, C1-3 alkyl, aralkyl or C3-5 alkenyl group, furthermore in which R1 and R3 are hydrogen and R2 is an aryl group have already been described in the literature, whereas the remaining derivatives of the general formula (I) are new. These compounds can be prepared by reacting a compound of the general formula (II) <IMAGE> (II) with an amine of the general formula (III), <IMAGE> (III) or by alkylating a compound of the general formula (IV). <IMAGE> (IV) In the above formulae X stands for halogen, hydroxy or C1-4 alkoxy, whereas R1, R2 and R3 have the meanings as defined above.
公开号:SU1389677A3
申请号:SU823491803
申请日:1982-09-20
公开日:1988-04-15
发明作者:Аттила-Киш-Тамаш；Юрак Ференц；Виг Золтан；Зубовитш Терез；Фекете Пал；Кулчар Юдит
申请人:Эдьт Дьедьсерведьесети, Дьяр (Инопредприятие)；
IPC主号:

专利说明:

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wasps
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ABOUT-(
eleven
This invention relates to a method for the ncijiyMeHviH of novel 2-cyano-2-phenylacetic acid 1 1 acids of the general form.
CN Oh
- s-s,
u
where R, is phenyl;
R is hydrogen; or K and R together
with the nitrogen atom form a morphological group; Rj is lower alkyl, which can be used in agriculture as a growth regulating agent.
The aim of the invention is to develop a method for producing new 2-cyano-2-phenylacetic acid derivatives, which have a higher activity.
Example 1. A solution of sodium ethylate is prepared from 23 g of anhydrous ethanol and 2.3 g (0.1 g atom) of sodium, to which an alcohol solution of 23.6 g of anilide 2-cyano is first added at 50 ° C. 2-phenylacetic acid, and then 12 g (0.11 mol) of ethyl bromide. The resulting precipitate containing the precipitate is refluxed until the pH reaches 7 (about 2 hours). Most of the ethanol is removed and the amount of ice-cold water needed to dissolve the sodium bromide is added to the residue. The mixture is extracted twice with 100 ml of benzene, the combined benzene solutions are washed with cold 20% sodium hydroxide solution and hydrochloric acid, dried over anhydrous sodium sulfate / potassium carbonate and evaporated. 17.1 g of 2-cyano-2-ethyl-1--2-phenyl-acetic acid anilide (compound A) are obtained. So pl, 110,4-112,4 ° C, yield 65%.
Calculated,%: C 77.25; H 6.09.
Found,%: C 77.86; H 6.33.
Similarly, a morpholide of 2- -cyano-2-ethyl-2-phenylacetic acid is obtained in 56% yield, m.p. 88-90 ° C.
Calculated,%: C 69.74; H 7.03; N 10.84.
Found,%: C 71.06; H 7.17; N 11.16.
Synthesized compounds are tested for growth regulating activity.
77 2
For this, test compounds are molded in the form of; wettable powder (WP), 80, the active agent is crushed to a grain size of 1-20 μm, then homogenized with a dispersing agent (10% sodium methyl alcohol and buried). An aqueous solution is prepared from the wettable powder.
The following test methods are used.
CO fixation j.
Plant segments (bean disc and corn leaf) were kept for 24 hours in a solution with concentrations of 20, 50, 100, 200, 500, 1000 and 2000 ppm, then fixed for 1 hour in a fixation system in the atmosphere of CO. 10 mg of BaSOE, having an activity of 57 mCi / mg, under constant illumination. Plant assimilation is stopped with liquid nitrogen and the plant segments are dried at 80-90 s. After homogenization, their activity is determined using a measuring device (combustion system, gas phase measurement). Insert amino acids. Plants are kept in a solution of test compounds with the above concentrations for 24 hours, then in a 1-C glycerol solution with an activity of 2 mCi / ml for 3 hours. They are ground to powder using liquid nitrogen and proteins are extracted: 10% - trichloroacetic acid , 80% - a mixture of alcohol - ether, then extracted. The residue is dissolved in 6 within 6 hours. After receiving a solution in an amount of 25 ml, it is used to measure activity using a liquid scintillation method with 5 parallel measurements.
Mean values of measurements are given in Table. 1 and 2, respectively, for corn and beans.
As can be seen from the data given in Tables 1 and 2, compounds A and B, obtained according to the proposed method, increase the assimilation of plants to a greater extent than the known compounds C and D.
In tab. 3 shows the data on green mass and yield.
The experiments were carried out with a fourfold repetition in greenhouses and greenhouses on a surface of 1 m and on cultivated cucumbers on peat nutritive soils on crops.
1389677
11 1 units I ae T.re compounds refer to low toxic-j compounds.

权利要求:
Claims (1)
[1]
Invention Formula
The method of obtaining derivatives of 2- -cyano-2-phenylacetic acid of the general formula
-v. CN Oh
Note: A
WITH
2-cyano-2-eth-2-phenylacetic acid anilide, 3,4-diphenyl-4-cyanobutanoic acid ethyl ester.
Note: B-morpholide 2-cyano-2-ethy-1-2-phenylacetic acid.
D - 2-isocyanopropionic acid benzylamide.
0
R is hydrogen} or R and K together with nitrogen form a morpholino group; Ke - low C, -C4 alksht; characterized in that the compound of general formula CN
iLi-c-K
 II RTable 2
Table 3
Control A B
About 1 1
2.78 3.20 3.52

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法律状态:

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