Potassium or hydrazinium salts of 4-dinitromethyl-1,2,3-triazoles, having herbicidal activity

FIELD: chemistry.

SUBSTANCE: invention describes novel potassium or hydrazinium salts of 4-dinitromethyl-1,2,3-triazoles of general formulae V-VIII: V, VI VII, VIII, where Kat+ =K+ (V,VII), NH2NH3+ (VI;VIII).

EFFECT: higher herbicidal activity.

1 cl, 2 tbl, 4 ex

 

The invention relates to the field of production of organic substances and can be used in the production of herbicides and other biologically active substances.

Known herbicides [application EN 2004110236/04, A01N 47/38, application EN 2005104088/04, C07D 249/14, application EN 2007103518/04, C07D 487/04], containing in its structure 1,2,4-triazole cycle associated with arylsulfonamides or sulfonylamine fragments. Patented compounds in combination with other components to improve the tolerance of cultivated plants of herbicides.

The closest to the claimed herbicides include herbicides [application EN 2004127655/04, C07D 403/04, application EN 2004127663/04, C07D 403/04], which are the antidotes from fetotoksicheskoe action of the herbicide 2,4-dichlorophenoxyacetic acid in germinating sunflower seeds. These herbicides are 1,2,3-triazole, associated with a 1,3,5-triazine ring. The disadvantage of these herbicides is a multistage process operations when they are received, and when an individual their application is more low biological activity.

The objective of this study is to develop a method of obtaining new herbicides from cheap and available source components without the use of complex technological operations. This suggested the use of potassium or hydrazinium salts 4-ACI-dinitromethyl-1,,3-triazoles of General formula V-VIII:

where Kat+=K+(V,VII), NH2NH3+(VI, VIII).

The basis of the method of obtaining potassium V, VII or hydrazinium VI, VIII salt is the reaction of nucleophilic substitution of the nitro - or ethoxycarbonyl group in the N-methylated substituted 4-dinitromethyl-1,2,3-triazole I-IV potassium or hydrazinium group in the presence of excess alcohol solution of potassium hydroxide or hydrazine hydrate with access to 87%.

I, III R=NO2, II, IV, R=CO2Et

The original N-methylated 4-trinitromethyl-1,2,3-triazole (I, III or N-methylated ethyl-1,2,3-triazole-4-Il dinitroaniline II, IV obtained by treatment with excess diazomethane respectively trinitroazetidine or ethyldiethanolamine by the method of [Dowel Structure and chemistry 4-trinitromethyl-1,2,3-triazoles. Diss.... Kida. chem. Sciences. SPb., 1991, 100 S.]. The output decomposition temperature, the electronic spectra of the obtained salts V-VIII are shown in table 1.

Table 1.
Formula, outputs, temperature decomposition and electronic spectra of potassium V,VII, hydrazinium VI,VIII salts 4-ACI-dinitromethyl-1,2,3-triazoles
No. Conn. The formula of the compoundOutput %So different. °C. (solvent for crystallization)Electronic range
ethanol, λmaxnm, (Ig ε)
V78198 (ethanol)232 (3.76)
365 (3.93)
VI80142 (methanol)232 (3.77)
365 (3.94)
VII80182 (ethanol)232 (3.73)
365 (3.97)
VIII87152 (methanol)232 (3.87)
365 (4.04)

Received technical R is the result allows to synthesize high yield potassium or hydrazinium salt 4-ACI-dinitromethyl-1,2,3-triazoles, and thus substances with herbicide activity. Thus, the set of essential features set forth in the claims, allows to achieve the desired result.

Examples of the proposed method of obtaining potassium or hydrazinium salts 4-ACI-dinitromethyl-1,2,3-triazoles V-VIII

Example 1

Potassium salt of 2-methyl-4-ACI-dinitromethyl-1,2,3-triazole (compound V). To a solution of 0.9 g (0,004 mol) of 2-methyl-4-trinitromethyl-1,2,3-triazole (I) in 10 ml of ethanol are added dropwise at 20°C and stirring a saturated alcoholic solution of potassium hydroxide until the termination of formation of a yellow precipitate V. salt Precipitate is filtered off and recrystallized from ethanol, to obtain 0.66 g (78%) of target compound. Potassium salt (V) is obtained by the counter synthesis of 0.7 g (of 0.003 mol) ethyl 2-methyl-1,2,3-triazole-4-yl of dinitroaniline (II) and an alcohol solution of potassium hydroxide, the yield of 0.44 g (73%).

Found, %: N 30,48. C4H4KN5O4.

Calculated, %: N 31,11.

Example 2

Gerasiyeva salt of 2-methyl-4-ACI-dinitromethyl-1,2,3-triazole (compound VI). To a solution of 0.9 g (0,004 mol) of 2-methyl-4-trinitromethyl-1,2,3-triazole (I) in 10 ml of ethanol are added dropwise at 20°C and stirring 50%alcoholic solution of hydrazine hydrate before the termination of the formation of a yellow precipitate of salt VI. The precipitate is filtered off and recrystallized from the of ethanol, obtain 0.7 g (80%) of target compound. Gerasiyeva salt (VI) obtained by the counter synthesis of 0.7 g (of 0.003 mol) ethyl 2-methyl-1,2,3-triazole-4-yl of dinitroaniline (II) and 50%aqueous alcoholic solution of hydrazine hydrate, the yield 0.45 g (75%).

Found, %: N 45,09. C4H9N7O4.

Calculated, %: N 44,74.

Example 3

Potassium salt of 1-methyl-4-ACI-dinitromethyl-1,2,3-triazole (compound VII). Received likewise the compound (V) of 0.9 g (0,004 mol) of 1-methyl-4-trinitromethyl-1,2,3-triazole (III) and an alcoholic solution of potassium hydroxide.

Solvent for recrystallization - ethanol, yield 0.7 g (80%). Potassium salt of (VII) obtained by the counter synthesis of 0.7 g (of 0.003 mol) of ethyl 1-methyl-1,2,3-triazole-4-yl of dinitroaniline (IV) and an alcoholic solution of potassium hydroxide, output and 0.46 g (77%).

Found, %: N 30,59. With4H4KP5O4.

Calculated, %: N 31,11.

Example 4

Gerasiyeva salt of 1-methyl-4-ACI-dinitromethyl-1,2,3-triazole (compound VIII). Received likewise the compound (VI) of 0.9 g (0,004 mol) of 1-methyl-4-trinitromethyl-1,2,3-triazole (III) and 50%aqueous alcoholic solution of hydrazine hydrate. Solvent for recrystallization : methanol, output 0,76 g (87%). Gerasiyeva salt (VIII) obtained by the counter synthesis of 0.7 g (of 0.003 mol) of ethyl 1-methyl-1,2,3-triazole-4-yl of dinitroaniline (IV) and 50%aqueous alcoholic solution of hydrazine hydrate, the yield of 0.48 g (80%).

Found, %: N 44,18. C4H9N O4.

Calculated, %: N 44,74.

Herbicide activity of the claimed compounds is ensured by the presence of 1,2,3-triazole ring, which is an antagonist of imidazole cycle triazole analogs of adenine and guanine [Boyer j. Heterocyclic compounds. Ed. Relerford. M., Mir, 1965, Vol.7, 295 C.]. Revealed that the presence of a common system of pairing 1,2,3-triazole ring with a double bond, nitro, carbonyl or carboxyl groups provides the manifestation of higher herbicide activity [Vereshchagin LI, G. Tikhonova, Maksimova AV, Gavrilov L.D., Girey family of GA Synthesis of acyl - and vinylsubstituted 1,2,3-triazoles. Journe. body chemistry. 1979, t.15, issue 3, s-618].

Test the biological effect of the claimed substances were performed in the laboratory bulk chemical analyses of the state scientific institution "all-Russian research Institute of irrigated vegetable and melon" (Astrakhan) by the method of serial dilution. The study found that salts of the General formula V-VIII show different herbicide activity against weeds barley, peas and radishes. The data obtained biological studies are shown in table 2. As a comparison used herbicide composition "Pyrazolate".

No. Conn.The compounds of formulaHerbicide activity, mg/ml
peasradishbarley
V20,020,020,0
VI20,020,020,0
VII40,040,040,0
VIII40,040,040,0
Herbicide composition "Pyrazolate"20,020,020,0

From the data of table 2 shows, the greatest weed-killing activity against weeds, peas, radish and barley have potassium salt of 2-methyl-4-ACI-dinitromethyl-1,2,3-triazole (V) and gerasiyeva salt of 2-methyl-4-ACI-dinitromethyl-1,2,3-triazole (VI).

Thus, the technical result is the synthesis of new potassium or hydrazinium salts 4-ACI-dinitromethyl-1,2,3-triazole, which are available to use as herbicides, as useful plants show good tolerability in the processing of these funds.

Potassium or hydrazinium salt 4-dinitromethyl-1,2,3-triazole of the General formulas V-VIII:

where Kat+=K+(V,VII), NH2NH3+(VI, VIII).



 

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The invention relates to a derivative of a simple ester, application and intermediate compounds used for their production

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SUBSTANCE: invention describes novel potassium or hydrazinium salts of 4-dinitromethyl-1,2,3-triazoles of general formulae V-VIII: V, VI VII, VIII, where Kat+ =K+ (V,VII), NH2NH3+ (VI;VIII).

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1 cl, 2 tbl, 4 ex

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SUBSTANCE: invention relates to agriculture. Presowing treatment of seeds of winter wheat is carried out with a mixture of aqueous solution "PMAG" polymethacrylateguanidine with a molecular mass of 500 thousand specific units, with a concentration of 0.2% with protectant Kinto Duo® (BASF) at a dose of 1.5 l/t at an operating flow of 15 litres per 1 ton of seeds.

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7 tbl, 4 ex

FIELD: chemistry.

SUBSTANCE: invention relates to agriculture. In order to protect vegetative sunflower plants from the damaging effect of 2,4-dichlorophenoxy acetic acid, said plants are treated with benzyl ether (4,6-dimethyltriazolo-[1,5-a]pyrimidyl-2-sulphanyl)-acetic acid of formula I: in amount of 200 g/ha, three days after applying the herbicide.

EFFECT: invention increases sunflower yield.

1 tbl

FIELD: chemistry.

SUBSTANCE: invention relates to agriculture. As active, composition contains combination of florasulam with 2,4-dihlorphenoxyacetic acid ether, necessary for obtaining its preparative form target additives and, at least, 0.1 wt % of 2,4- dichlorophenoxyacetic acid. As ether of 2,4-dihlorphenoxyacetic acid, composition contains 2-ethylhexyl or isooctyl ether of 2,4-dihlorphenoxyacetic acid, and as target additives - SAS, solvent, defoamer, antifreeze, thickener, biocide and acidity regulator. Weed plants and place of their vegetation are treated with effective quantity of herbicidal composition.

EFFECT: invention makes it possible to obtain stable and safe in application preparative forms of herbicidal compositions, stable in prolonged storage and able to suppress weed plants in grain crops and maize.

6 cl, 3 tbl, 6 ex

FIELD: chemistry.

SUBSTANCE: described are preparations, which possess fungicidal activity, containing hydrazones of nitro-1,2,3-tiazol-4-yl-carbaldehyde of formula

Ia-c,

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EFFECT: improved qualities of claimed preparations.

1 tbl, 4 ex

FIELD: chemistry.

SUBSTANCE: invention relates to agriculture, in particular to means for fighting undesirable vegetation. A herbicidal composition is created on the base of a sinergically effective combination of sulphonylureas (I) and triazolopyrimidines (II). The ratio of active substances (I) and (II) changes in the range from 1:5 to 5:1. A mixture of agriculturally acceptable adjuvants from the group of ethoxylated fatty alcohols and organosilicon compounds from the class of silixane is added to the said composition. The ratio of ethoxylated fatty alcohols and siloxanes in the mixture changes in the range from 1:10 to 10:1 respectively. A mixture of isodecyl alcohol ethoxylate with an organosilicon compound as an adjuvant is applied. In order to fight undesirable vegetation in crops of cultivated plants an effective quantity of the herbicidal composition is applied on it.

EFFECT: obtaining the means for fighting undesirable vegetation.

13 cl, 4 tbl, 2 ex

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