Antidote against phytotoxic effect of herbicide 2,4-dichlorophenoxyacetic acid

FIELD: organic chemistry, herbicides, agriculture.

SUBSTANCE: invention describes using 2-morpholyl-6-piperidyl-4-[(4'-(ethoxycarbonyl-5'-1',2',3'-triazol)-1'-yl]-1,3,5-triazine of the formula: as an antidote against phytotoxic effect of herbicide 2,4-dichlorophenoxyacetic acid on sunflower germinated seeds. The proposed substance allows significant increasing roots and hypocotyls length of seedlings and to expand assortment of the known antidotes.

EFFECT: improved and valuable properties of antidote.

2 cl, 2 tbl, 3 ex

 

The invention relates to the field of chemistry and agriculture, specifically to the derived series of 1,3,5-triazine as a compound that protects against fetotoksicheskoe actions of herbicides in the cultivation of sunflower (antidote).

Known 1.2-dioxymethylene (DMK) formula:

used to protect plants from sunflower fetotoksicheskoe action of 2,4-dichlorophenoxyacetic acid and its butyl ether (herbicide 2,4-D and EB 2,4-D) [see Chemical encyclopedic dictionary. - M.: Soviet encyclopedia, 1983, s]. The disadvantages of using DMK are low efficiency, relatively high costs of its (200 g/ha of the active ingredient), the inability to effectively increase the length of roots of sunflower seedlings and yield on the background of the use of herbicides and the need for soil application.

Also known 2-methoxy-4-morpholin-6-[(4'-phenylcarbamoyl-5'-methyl-1',2',3'-triazole)-1'-yl]-1,3,5-triazine (MFT) formula:

which is the antidote from fetotoksicheskoe action of the herbicide 2,4-D on the germinating seeds and seedlings of sunflower [see Pat of the Russian Federation No. 2230066 (10.06.2004,); IPC707 D 403/04, A 01 N 43/68; Snehalata Ask, Ightmare, Avezov, Nscontrol, Vinsanity 2-Methoxy-4-morpholin-6-[(4'-phenyl-carbonyl-5'-methyl-1',2',3'-triazole-1'-yl]-1,2,3-triazine in ka is este antidote. Bull. Fig. 2004, No. 16]. The disadvantage of its use is relatively low activity in reducing fetotoksicheskoe action of the herbicide 2,4-D on seeds and seedlings of sunflower.

Technical solution to the problem is a more effective increase in the length of roots and hypocotyls of seedlings of sunflower in the background fetotoksicheskoe action of herbicides of the group of 2,4-D, as well as extending the range of known antidotes.

The task is achieved by using 2-morpholin-6-piperidin-4-[(4'-etoxycarbonyl-5'-methyl-1',2',3'-triazole)-1-yl]-1,3,5-triazine (NET) formula:

as an effective antidote from fetotoksicheskoe action of the herbicide 2,4-dichlor-phenoxyalkanoic acid in sunflower.

The novelty of the claimed proposal is seen in the use of previously known ("Ambinter Stoks Screening Collections" 01.01.2004, No. 442660-20-0 .IS) connection 2-morpholin-6-piperidin-4-[(4'-etoxycarbonyl-5'-methyl-1',2',3'-triazole)-1-yl]-1,3,5-triazine, NET (information about applying as a antidote in the literature are absent) as the antidote of seedlings and vegetative plants of sunflower, which allows to increase the length of the roots and hypocotyls of seedlings of sunflower.

At the same time, NET get known method the interaction of the corresponding 2-azido-4,6-disubstituted 1,3,5-triazines with equimolar to the number methylene-active dicarbonyl compounds in solution, in dimethylformamide, in the presence of triethylamine at a temperature of 30-40° [see General organic chemistry / edited by Dbarton and Udelays. - M.: Chemistry. 1981, vol. 1, s]. The original 2-azido-4,6-disubstituted 1,3,5-triazine also get a known method [see Weigand-Hilgetag. Methods experiment in organic chemistry. - M.: Chemistry, 1969. s].

Used acetoacetic ether, dimethylformamide and triethylamine immediately before use are cleaned and dried by known methods [see Agordon, Rford. Satellite chemist. M.: Mir, 1976. - 541 S.].

Examples of obtaining below.

Example 1. 2-Morpholin-6-piperidin-4-[(4'-etoxycarbonyl-5'-methyl-1',2',3'-triazole)-1'-yl]-1,3,5-triazine (MPAT). To a solution of 2.92 g (0.01 mol) 2-azido-4-morpholin-6-piperidin-1,3,5-triazine in 20 ml of dried and purified dimethylformamide under stirring at a temperature of 20±1°With added dropwise a mixture of 2.6 g (0.02 mol) of acetoacetic ester and 2.02 g (0.02 mol) of dry and fresh of triethylamine. The reaction mixture is stirred for 40 h at 35-40°and when mixing a squirt poured into 100 ml of chilled 10°With water. The resulting white precipitate is filtered off, washed thoroughly with water from the remnants of the solvent and triethylamine and dried at 50-60°C. Receive 2,47 g (85,0%) NET in the form of a white powder with TPL 198-199°insoluble in water, but rastvorimogo in polar organic solvents.

Found, %: C 53,90; N. Of 6.65; N 27,99. C18H26N8O3. Calculated, %: C 53,71; N 6,51; N 27,85.

X νcm-1(group): 1710 cf. (C=O); 1600, 1550 C. (C=C, C=N, N=N - t. and cyanurates cycle.); 1150, 1100 cf. s-O-S.

TMR, δ, ppm (group): 4,32-4,40 (2N square, co2CH3J=4,5); 3,65-3,85 (N, m, NCH2+Co2); 2.83 (3H S.=CLO3); 1,53-1,73 (6N m, CH2piperidyl)); 1.32-1.40 (3H, t, OCH2CH3) J=4,5.

Mol. ion (mass by a spectroscope) 402.

Example 2. 2-Morpholin-6-piperidin-4-[(4'-etoxycarbonyl-5'-methyl-1',2',3'-triazole)-1'-yl]-1,3,5-triazine (MPAT). Under conditions analogous to example 1, of 2.92 g (0.01 mol) 2-azido-4-morpholin-6-piperidin-1,3,5-triazine, 2.6 g (0.02 mol) of acetoacetic ester and 2.02 g (0.02 mol) of dry and fresh of triethylamine, with the only difference that the addition of acetobromo ether and triethylamine carried out at 25±1°and continue stirring the mixture for 35 h at 40-45C, get 2,47 g (85,0%) NET in the form of a white powder with TPL 198-199°insoluble in water, but soluble in polar organic solvents.

Found, %: C 53,90; N. Of 6.65; N 27,99. With18H26N8About3. Calculated, %: C 53,71; N 6,51; N 27,85.

X νcm-1(group): 1710 cf. (C=O); 1600, 1550 C. (C=C, C=N, N=N - t. and cyanurates cycle.); 1150, 1100 cf. s-O-S.

TMR, δ, ppm (group): 4,32-4,40 (2N square, co2CH3J=4,5); 3,65-3,85 (N, m, NCH2+Co2); 2.83(3H C. C=CLO3); 1,53-1,73 (6N m, CH2piperidyl)); 1.32-1.40 (3H, t, och2CH3) J=4,5.

Mol. ion (mass by a spectroscope) 402.

NET use to reduce fetotoksicheskoe action of the herbicide 2,4-D on germinated seeds (seedlings) of sunflower in laboratory experience. While preparing for his workers aqueous solutions of concentrations from 0.01 to within 0.00001 wt.% and treated germinated sunflower seeds varieties VNIIMK 8883, pre-sprayed with a water dispersion of 2,4-D (standard)*as shown below in example 3. For comparison, using an aqueous solution MFT (prototype). Due to the poor solubility in water, used MFT, EAT and 2,4-D pre "podrastet" in a small amount of alcohol. As a control, use the option of processing water.

Example 3. In laboratory experience germinated on constantly moist filter paper in a Petri dish sunflower seeds (25 seeds per Cup in five replicates) after 4 days from the beginning of germination at 23°subjected to sequential exposure to aqueous dispersions of the herbicide 2,4-D, and after 1 h the aqueous solution was NAT a given concentration. Continue germination under the same conditions for another 3 days and determine the root length of seedlings (data bring to the table). The decrease in root length and hypocotyl in the advanced options compared to the control (A mindin % is determined by the formula:

Amind=(K/K)·100,

where To and length of seedlings in the control and experimental variants, respectively.

Examples 4-9 carry out strictly the same experience 3 way. To control spending experience 4 using only water (control), as well as experience using only the herbicide 2,4-D in the specified concentrations (reference). For comparison, in similar conditions and conduct experiments using as an antidote known connections MFT.

All experimental data are subjected to statistical analysis using t-student test at a confidence level of 0.95.

As can be seen from the data table. 1, the application on the background of the impact of the herbicide 2,4-D connection 2-Morpholin-6-piperidin-4-[(4'-etoxycarbonyl-5'-methyl-1',2',3'-triazole)-1'-yl]-1,3,5-triazine (NAT) provides in comparison with the standard increase in root length of seedlings of sunflower by 51.6-67,74% (47-52 mm instead of 31 mm in the case of the standard), while the use of known means MFT provides an increase of only 23.1-46,0% (32-38 mm instead of 26 mm in the case of the standard). It is also clear that if as a result of fetotoksicheskoe steps of the standard length of the hypocotyl of seedlings is reduced in comparison with the control 64,5%, (30 mm instead of 66), the use of NET reduces fetotoksicheskoe herbicide action and the length of the hypocotyl increases when Anenii with reference to 43.3-73,3% (45,0-52 mm), while the use of known compounds prototype MFT - reduces this figure only 8.9-14.3 per cent.

Thus, the use as an antidote compounds (NAT) allows the background fetotoksicheskoe impact of herbicide to increase the length of the roots and hypocotyls of seedlings, as well as to expand the range of known antidotes.

Table 1

Antidote activity of the synthesized compounds in relation to the length of the root
ConnectionRoot length, mm2,4-D + safener in concentration, wt.%*
Control (water)2,4-D (standard)10-210-310-410-5
Root length, mm% benchmark*Root length, mm% benchmark*Root length, mm% benchmark*Root length, mm% benchmark*
Examples:456789
9126374234,532,738463223,1
104314751,65267,744958,064854,84

Table 2

Antidote activity of the synthesized compounds in relation to the length of the hypocotyl
ConnectionThe length of the hypocotyl, mm2,4-D + safener in concentration, wt.%*
Control (water)2,4-D (standard)10-210-310-410-3
Root length, mm% benchmark*Root length, mm% benchmark*Root length, mm% benchmark*Root length, mm% benchmark*
Examples:456789126374234,532,738463223,1
66304756,75273,34963,34543,3

Application 2-morpholin-6-piperidin-4-[(4'-etoxycarbonyl-5'-methyl-1'2'3'-triazole)-1-yl]-1,3,5-triazine (NET) formula

as an antidote from fetotoksicheskoe effects of the herbicide 2,4-dichlorophenoxyacetic acid on the sprouted sunflower seeds.



 

Same patents:

FIELD: organic chemistry, medicine, virology.

SUBSTANCE: invention relates to new derivatives of piperidine of the general formula (II): or their pharmaceutically acceptable salts wherein Xa means -C(R13)2-, -C(R13)(R19)-, -C(O)-, and others; Ra means R6a-phenyl or phenyl substituted with methylsulfonyl; R1 means hydrogen atom or (C1-C6)-alkyl; R2 means R7-, R8-, R9-phenyl wherein R7-, R8 and R9 mean substituted 6-membered heteroaryl and others; R3 means R10-phenyl, pyridyl and others; R4 means hydrogen atom, (C1-C6)-alkyl, fluoro-(C1-C6)-alkyl; R6a means from 1 to 3 substitutes taken among the group involving hydrogen, halogen atom, -CF3 and CF3O-; R7 and R8 mean (C1-C6)-alkyl and others; R9 means R7, hydrogen atom, phenyl and others; R10 means (C1-C6)-alkyl, -NH2 or R12-phenyl wherein R12 means hydrogen atom, (C1-C6)-alkyl and others; R13, R14, R15 and R16 mean hydrogen atom or (C1-C6)-alkyl; R17 and R18 in common with carbon atom to which they are bound form spirane ring comprising from 3 to 6 carbon atoms; R19 means R6-phenyl wherein R6 means R6a or methylsulfonyl; R20, R21 and R22 mean hydrogen atom or (C1-C6)-alkyl; R23 means (C1-C6)-alkyl under condition that if Ra means phenyl substituted with methylsulfonyl then Xa can mean the group only. Compounds of the formula (II) possess properties of CCR5-antagonist and can be used in medicine in treatment of HIV-infection.

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15 cl, 1 dwg, 12 tbl, 15 ex

FIELD: organic chemistry, agriculture.

SUBSTANCE: invention describes a new compound 4,6-bis-(morpholyl)-2-[(2'-ethoxyacetyltetrazolyl)-5'-yl]-1,3,5-triazine of the formula: that represents an antidote against phytotoxic effect of herbicide 2,4-dichlorophenoxyacetic acid on germinating sunflower seeds and seedlings.

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2 cl, 2 tbl, 3 ex

FIELD: organic chemistry, medicine, pharmacy.

SUBSTANCE: invention relates to new nitrogen-containing aromatic derivatives of the general formula:

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40 cl, 51 tbl, 741 ex

FIELD: organic chemistry, pharmacy.

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36 cl, 4 sch, 1 tbl, 21 ex

FIELD: organic chemistry, heterocyclic compounds, medicine.

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7 cl, 1 tbl, 3 ex

FIELD: organic chemistry, medicinal biochemistry, pharmacy.

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EFFECT: valuable medicinal properties of compounds and composition.

4 cl, 7 tbl, 224 ex

FIELD: organic chemistry, medicine, pharmacy.

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19 cl, 1 dwg, 5 tbl, 122 ex

FIELD: organic chemistry, medicine, pharmacy.

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26 cl, 4 tbl, 476 ex

FIELD: organic chemistry, medicine, pharmacy.

SUBSTANCE: invention describes derivative of aroylpiperazine of the formula (I):

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EFFECT: improved preparing method, valuable medicinal properties of compounds and pharmaceutical composition.

8 cl, 94 ex

FIELD: organic chemistry, chemical technology, agriculture.

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EFFECT: improved preparing methods, valuable properties of compounds.

13 cl, 5 tbl, 18 ex

FIELD: organic chemistry, herbicides, agriculture.

SUBSTANCE: invention describes using 2-pyrrolidine-6-diphenylamino-4-[(4'-ethoxycarbonyl-5'-methyl-1',2',3'-triazol)-1'-yl]-1,3,5-triazine of the formula: as an antidote against phytotoxic effect of herbicide 2,4-dichlorophenoxyaxetic acid on sunflower germinated seeds. The proposed compound allows significant increasing roots and hypocotyls length of seedlings and to expand assortment of the known antidotes.

EFFECT: valuable properties of antidote.

2 cl, 2 tbl, 3 ex

FIELD: organic chemistry, herbicides, agriculture.

SUBSTANCE: invention describes using 4,6-bis-(diethylamino)-2-[(2'-tetrazol-(2'H)-5'yl]-1,3,5-triazine of the formula: as an antidote against phytotoxic effect of herbicide 2,4-dichlorophenoxyacetic acid on sunflower germinated seeds. The proposed substance shows the enhanced effectiveness in increasing roots and hypocotyls length of seedlings and to expand assortment of the known antidotes.

EFFECT: valuable properties of antidote.

2 cl, 2 tbl, 3 ex

FIELD: agriculture, in particular warm-season crop cultivation.

SUBSTANCE: claimed method includes preliminary stimulation of weed growth followed by ravage thereof and drilling into soil. Roundup herbicide in introduced in autumn for 5-10 days before under-winter ploughing, and in spring one half of Roundup dose in mixture with potassium humate in amount of 2-3 kg/hectare is introduced.

EFFECT: method of improved efficacy; decreased soil toxicity; increased fertility.

2 tbl, 2 ex

FIELD: agriculture, in particular plant protection.

SUBSTANCE: claimed method includes plant treatment with composition containing at least one toxic material and target additives. As target additive 3-day suspension of green alga Chlorella vulgaris is used.

EFFECT: reduced consumption of toxic material, decreased stress action on agriculture plants, decreased accumulation and migration toxic substances in soil and plants.

2 cl, 1 tbl, 11 ex

Herbicidal agent // 2266648

FIELD: organic chemistry, agriculture.

SUBSTANCE: invention relates to herbicidal agent containing effective amount of active compound mixture including a) 2-(2-methoxycarbonylsulfonyl aminocarbonyl)-4-methyl-5-propoxy-2,4-dihydro-3H-1,2,4-triazole-3-one of general formula I 1 or sodium salt thereof; and b) one compound improving resistance of agriculture plants, namely diethyl-1-(2,4-dichlorophenyl)-4,5-dihydro-5-methyl-1H-pyrazole-3,5-licarboxylate in ratio a/b of 1:0.025-25 pts.

EFFECT: herbicidal agent reducing damage of agriculture plants, in particular cereals.

1 cl, 24 tbl, 2 ex

FIELD: organic chemistry, agriculture.

SUBSTANCE: invention describes a new compound 4,6-bis-(morpholyl)-2-[(2'-ethoxyacetyltetrazolyl)-5'-yl]-1,3,5-triazine of the formula: that represents an antidote against phytotoxic effect of herbicide 2,4-dichlorophenoxyacetic acid on germinating sunflower seeds and seedlings.

EFFECT: valuable properties of compound.

2 cl, 2 tbl, 3 ex

FIELD: organic chemistry, herbicides, agriculture.

SUBSTANCE: invention describes a composition showing the selective effect and comprising as conventional inert adjuvants and the following mixture as an active component: a) effective amount of compound of the formula (I): as a herbicide wherein each R1 and R3 means independently of one another (C1-C4)-alkyl; R4 and R5 mean the group: -C-R14(R15)-C-R16(R17)-O-R18(R19)-C-R20(R21)-(Z2) wherein R14, R15, R16, R17, R18, R19, R20 and R21 mean hydrogen atom; G means hydrogen atom, -C(X1)-R30, alkaline metal cation, earth-alkaline metal cation, sulfonium or ammonium cation; X1 means oxygen atom; R30 means hydrogen atom, (C1-C10)-alkyl, and salts and diastereomers of compounds of the formula (I) under condition that R1 and R3 don't methyl group simultaneously; b) effective amount of protective agent (antidote) for prevention of hazard effect of herbicide wherein antidote is taken among the group comprising clochintocet, clochintocet with alkaline metal cation, earth-alkaline metal cation, sulfonium or ammonium cation, clochintocet-mexil, mefenpir, mefenpir with alkaline metal cation, earth-alkaline metal cation, sulfonium or ammonium cation and mefenpir-diethyl, and c) additive comprising (C8-C22)-saturated acids alkyl ester or emulsified vegetable oil, or mineral oil taken in the amount 0.01-2% as measured to the spraying mixture mass. Also, invention describes a method for selective control of weed and grassy plants in cultural plant plantings that involves using the abovementioned composition for treatment. Invention provides the selective effect in control of weed and grassy plants, in particular, in cereals crops plantings.

EFFECT: improved control method, valuable agricultural properties of composition.

3 cl, 8 tbl, 2 ex

FIELD: organic chemistry, agriculture.

SUBSTANCE: invention relates to selective herbicidal compositions, containing customary auxiliary substances, as well as: a) herbicidal effective amount of compound of formula I or agriculture acceptable salt thereof wherein R are independently C1-C6-alkyl, C1-C6-haloalkyl, C1-C4-alcoxy-C1-C4-alkyl, or C1-C4-alcoxy-C1-C4-alcoxy-C1-C4-alkyl; m = 2; Q is group of formula wherein R23 is hydroxyl and Y is C1-C4-alkylen bridge; and b) synergetically effective amount of one or more herbicides; and methods for controlling of undesired plants in tame cultures using the said composition. Also disclosed is composition containing customary auxiliary substances, as well as herbicidal and synergetically effective amount of 4-hydroxy-3-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)bicyclo[3.2.1]octo-3-ene-2-one of formula 2.2 and herbicidal antagonistically effective amount of antidote of formula 3.1. Compositions based on 4-hydroxy-3-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)bicyclo[3.2.1]octo-3-ene-2-one and herbicidal antagonistically effective amount of antidote, as well as methods for controlling of weeds and cereal grasses in tame cultures also are described.

EFFECT: compositions useful in effective controlling of many weeds both in pre-spring and post-spring phases.

5 cl, 63 tbl, 12 ex

FIELD: agriculture.

SUBSTANCE: invention describes a chitosan-base composition reducing the content of nitrates in plant growing production. The composition comprises chitosan of molecular mass 20-150 kDa, organic acids - mixture of succinic, ascorbic and sorbic acids in the mass ratio = 2:1:1, respectively, activating agents of nitrate and nitrite reductases - iron nitrate, ammonium molybdate, indolyl acetic acid and ethylenediaminetetraacetic acid in the mass ratio = 20:5:1:1, respectively; or iron nitrate, ammonium molybdate, indolyl acetic acid and N,N-dicarboxymethylglutamic acid in the mass ratio = 20:5:1:1, respectively, and substances enhancing synthesis of chlorophyll - 2-oxoglutaric acid and L-glutamic acid in the mass ratio = 30:1, and a surface-active substance also in the following ratio of above indicated components, wt.-%: chitosan, 15-25; organic acids, 15-25; activators of nitrate and nitrite reductases, 25-30; enhancers of chlorophyll synthesis, 29-35, and surface-active substance, 1-3. The composition provides enhancing assimilation of inorganic nitrogen in plant and reduces the content of nitrates in plant growing productions.

EFFECT: valuable properties of composition.

5 tbl

FIELD: agriculture.

SUBSTANCE: invention relates to application of 2-chloro-4,6-bis[thiophenyl]-1,3,5-triazine as antidote to reduce phytotoxic action of 2,4-dichlorophenoxyacetic acid butyl ester thereof to sunflower germs end vegetating plants.

EFFECT: effective increase of root length and sunflower yield.

2 tbl, 8 ex

FIELD: agriculture, insecticides.

SUBSTANCE: invention relates to insecticide covers for seeds that comprise one or some binding substances taken among the group including polymers and copolymers of polyvinyl acetate, methylcellulose, polyvinyl alcohol, vinylidene chloride, acryl, cellulose, polyvinylpyrrolidone and polysaccharide, and insecticide and a filling agent also. A binding agent forms matrix for insecticide and a filling agent. Also, invention relates to a method for control of insect-pests that involve applying a cover on seeds. Also, invention relates to a method for preparing seeds with cover that involves mixing a binding agent, carrier and insecticide, applying a mixture of seed, drying and applying an additional filming cover. Method for protecting the germinating seedlings involves applying the insecticide cover on seeds. Invention provides reducing the phytotoxic effect of insecticide on seeds.

EFFECT: valuable agricultural properties of insecticide cover.

24 cl, 5 tbl, 5 ex

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