Substituted n-arylcarbamoyl as growth regulators for cotton


(57) Abstract:

Usage: as growth regulators for cotton. The inventive product - dimethyl - N - (4 - were)carbamoylphosphate. BF C10H14NO4P. an Output of 60% so pl. 98 - 100°C, dimethyl - N - (4 - chlorophenyl)carbamoylphosphate. BF C9H11ClNO4P output 70% so pl. 97 - 99°C. Reagent 1: (CH3O)2P(O)H , reagent 2: compound f-ly 1, where R is CH3or Cl. Reaction conditions: in the presence of catalytic amounts of triethylamine at 50°C. the Structure of the compound f-ly 1 5 table.

The invention relates to the chemistry of organophosphorus compounds, namely substituted carbamoylphosphate General formula I,

P where R = CH3Cl, which can find application in agricultural practice as growth regulators for cotton.

Cotton (Gossipium hirsutum, G. barbadense) is a perennial plant, which in the climatic conditions of the Central Asian region may not fully realize the nature of opportunities. For example, in the budding phase of this plant forms a large number of bolls (boxes). However, by the beginning of a reduction in day length and lower average daily temperature pororoca falls. It wastes biomass plants.

These characteristics of vegetation cotton was the prerequisite to study the influence of different plant growth regulators on yield of cotton.

Known N-substituted carbamoylphosphate General formula II

where R is alkyl; R1Is h, alkyl; R2- H, alkyl, -NR3R4; R3and R4- H, alkyl [1].

Also known N-substituted carbamoylphosphate General formula III

where R is alkyl; R1Is h, alkyl; R2- H, alkyl, -NR3R4; R3and R4Is h, alkyl; M is - NH4, Na, K [2].

Compounds of General formula II and III have astragalina activity and can find application in ornamental floriculture as growth inhibitors and retardants, as well as to increase the sugar content in fruits and sugar cane.

It is known that ammonium salt of monoethylene ether carbamoylphosphate acid (foamin or credit) formula

C is used as a herbicide to combat wood-shrub vegetation [3].

The closest analogues according to the chemical structure are substituted N-arylcarbamoyl total , R1- 4-Cl-C6H4; R - C2H5; C3H7i-C3H7i-C4H9, R1- 4-Br-C6H4; R - C2H5; C3H7i-C3H7i-C4H9, R1- 4-NO2C6H4; R - CH3C2H5C3H7i-C4H9C4H9. Compounds of General formula IV is produced by interaction of dialkylphosphites with arylisocyanate in the presence of tertiary amines or alcoholate [4]. Information about the biological activity of these compounds in the literature is not available.

Thus, among the known structural analogues of the claimed compounds not detected substances with astragalina activity against cotton.

At the present time to increase the productivity of cotton is 2-methyl-5-chlorobenzimidazole (Rosalyn) formula

CH3As of 0.001%-aqueous solution of this substance is used to prevent fall bolls of cotton spraying flowering and budding, which leads to increased yield of cotton at 3-5 kg/ha [5,6]. In higher concentrations Rosalyn shows herbicide properties, causing damage to plants.

The aim of the invention is to increase cotton yields over a wide range of concentrations of growth regulator.

This goal is achieved by obtaining new substituted N-arylcarbamoyl General formula I.

According to the invention substituted N-arylcarbamoyl get by a known method [4] by the interaction of dimethylphosphite 4-chlorophenyl or 4-methylphenylsiloxane in the presence of catalytic amounts of triethylamine or sodium salt dimethylphosphoric acid in aprotic solvents (benzene, toluene) or without them. The process is expediently carried out at 40-60aboutC.

The compounds of General formula I are white crystalline substances, soluble in alcohols, acetone, insoluble in water, sparingly soluble in benzene; in aqueous ammonia or hydrolyzed with the formation of salts monoamino substituted N-arylcarbamoyl acids.

Costumes spectrometry.

IR spectra (vaseline oil) contain absorption bands corresponding to the known types of connections: R-O-C at 950-1040 cm-1P=About when 1230-1280 cm-1, amide I at 1670-1680 cm-1, amide 11 at 1540-1600 cm-1in the form of two bands of N-H in 3320-3400 cm-1.

In the mass spectra of the obtained compounds of formula I are signals of molecular ions, indicating sufficient stability of the N-arylcarbamoyl to electronic attack. Dimethyl-N-(4-chlorophenyl)carbamoylphosphate has an intense signal of the molecular ion with m/e 263-264, and dimethyl-N-(4-were)carbamoylphosphate-243. Fragmentation occurs with rupture of the P-C bond migration of a proton or without it, for example



Further fragmentation of debris flows by known mechanisms.

P R I m e R 1. Dimethyl-N-(4-were)carbamoylphosphate. [K-8480].

To a mixture of 33 g (0,3 mol) of dimethylphosphite and 1.5 ml of triethylamine are added under stirring and cooling 39 g (0,3 mol) 4-methylphenylhydrazine, ensuring that the temperature of the reaction mixture did not exceed 50aboutC. After 1 h the reaction mass solidifies. Cleaning produce by recrystallization from isopropanol. Get 43,6 g (60%) of dimethyl-N-(4-(were) the14NO4P.

Calculated, %: 49,38; N 5,76; N 5,76.

P R I m m e R 2. Dimethyl-N-(4-chlorophenyl)carbamoylphosphate. [K-8482].

To a mixture of 39 g (0,355 mole) of dimethylphosphite and 1.5 ml of triethylamine are added under stirring and cooling of 54.5 g (0,355 mole) 4-chlorophenylalanine, ensuring that the temperature of the reaction mixture did not exceed 50aboutC. After 1 h the reaction mass solidifies. Cleaning produce by recrystallization from isopropanol. Get 65,5 g (70%) of dimethyl-N-(4-chlorophenyl)carbamoylphosphate. So pl.= 97-99aboutC.

Found, %: C 41,08, 41.03; H 4,10, 4,14; N 5,38, 5,41.


Calculated, %: 40,99; N 4,17; N 5,31.

Test compounds of General formula I on astragulus activity conducted on the upland cotton varieties EN+Uzbekistan-3 and Boycut-2 (G. hirsutum) and fine grade of C-6037 (G. barbadens) water suspensions of drugs: when plants are 4-6 true leaves, in the phase of mass of budding and after the formation on the plants specified number (15-20) of boxes. As a reference used Rosalyn. The results of the tests conducted in table. 1-4. Biological tests showed that the treatment drugs Konzentrat the next. The final harvest for these concentrations of the drugs increased in comparison with the control 15-34%.

It was noted that the variant with the processing of preparations in a concentration of 0.05% survived more podorvanov than in control. However, drugs are not completely exclude the abscission of ovaries, which by the time the third processing has not reached 10-15 days of age. It is shown that the boxes have reached the moment of processing more than 20 days, matured 5-7 days earlier than the control. Accounting final harvest showed that the treated preparations bushes to 10-15 October, all the boxes had time to Mature, whereas the control plants harvest food was lalsa to 20-25 November. Yield increase is also associated with a significant increase in the average weight of one of the boxes.

Positive should also be considered as partial falling of the leaves of the lower and middle tiers to the beginning of ripening. This improves air and light conditions for maturing bolls.

Additional benefits of compounds can be attributed to the ease of synthesis of the claimed compounds from available connections. The corresponding isocyanates can be obtained by postironium available n-Chloroaniline and n-truelover)carb - Molfetta LD16570 mg/kg LD501100 330 mg/kg LD841620 mg/kg, and dimethyl-N-(4-were)karamolegos-fonate LD161050 mg/kg LD501225 101 mg/kg LD841400 mg/kg Thus, the claimed N-arylcarbamoyl belong to low-toxic compounds with LD50> 1000 mg/kg

Astragalina activity of preparations To-8480 and-8482 is also evident on the pre-treatment of cotton seeds. Data from laboratory testing are given in table. 5. As the test object took the seeds of cotton cultivar C-4727.


Substituted N-arylcarbamoyl General formula

< / BR>
where R is CH3or Cl,

as growth regulators for cotton.


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16 cl, 10 tbl, 87 ex

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2 tbl, 10 ex

FIELD: organic chemistry, biochemistry, medicine.

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1 tbl, 3 ex

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