[2-trimethylammoniumchloride-4,6 - bis(ethoxycarbonylmethylene)]-1,3,5 - triazine, which is the antidote
(57) Abstract:Describes the new Quaternary salt [2-trimethylammoniumchloride-4,6-bis(ethoxycarbonylmethylene)] -1,3,5-triazine, which is the antidote from fetotoksicheskoe action of the herbicide 2,4-dichlorophenoxyacetic acid and its butyl ester of sunflower. The technical result is an effective increase in root length and yield of sunflower in the background fetotoksicheskoe of herbicides. table 2. The invention relates to the field of chemistry and agriculture, specifically to the derived SIM-triazine [2-trimethylammoniumchloride-4,6-bis(ethoxycarbonylmethylene)]-1,3,5-triazine (THAT) formula
< / BR>as compounds that protect against fetotoksicheskoe actions of herbicides in the cultivation of sunflower (antidote).Known trimethylammonium salt derivatives SIM-triazine containing alkylamino substituents in positions 4,6-triazino cycle, such as-N(CH3)2and-N(C2H5)2that are used as intermediates in the reactions of cyclization upon receipt bicyclic annelated derivatives SIM-triazine [see centuries Dovlatyan, K. A., Eliasen, A. C. Dovlatyan. Peregriono in the synthesis of compounds with antidote activity is unknown.It is also known the use of 1,2-dioxymethylene (DMK) formula:
< / BR>as a soil antidote protecting sunflower plants from 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. 550]. The disadvantages of using DMK are poor solubility in water and the necessity of preliminary bodrstvovaniya in alcohol, 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.The technical solution is an effective increase in root length and yield of sunflower in the background fetotoksicheskoe of herbicides.This object is achieved by obtaining a new Quaternary salt [2-trimethylammoniumchloride-4,6-bis(ethoxycarbonylmethylene)]-1,3,5-triazine (THAT) formula
< / BR>which can be used as an effective, water-soluble antidote from fetotoksicheskoe d is as stated suggestions seen in what a new Quaternary salt of ethyl ether triazine-carboxylic acid as an antidote vegetative plants of sunflower that can increase the length of the roots of seedlings and seed yield of sunflower. Salt has a high solubility in water, which simplifies the technology of preparation of working solutions and their application.At the same time declared Sol receive a known method by the reaction of 2-chloro-4,6-bis(ethoxycarbonylmethylene)-SIM-triazine with an excess of dry trimethylamine with 101o[See centuries Dovlatyan, K. A., Eliasen, A. C. Dovlatyan. Rearrangements in the row halogenoalkane(amino)-s-triazines.- CHC. 1977, 7, S. 989 - 992] . Source cyanuric chloride immediately prior to use purify by crystallization from carbon tetrachloride. Ethyl ester of glycine - get [see E. Fisher. Ber., 190], Bd.34, p. 433]. The triethylamine and benzos cleaned and dried by [see A. Weisberger, E., Proskauer, J. Riddick, E. Tops. Organic solvents. Izd-vo IL, M: 1958, - 517 S.].Examples of performance stated suggestions are presented below.Example 1. [2-Trimethylammoniumchloride-4,6-bis(ethoxycarbonylmethylene)] -1,3,5-triazine (THAT). The solution to 4.62 g (24 mmol) of 2,4,6-trichloro-1,3,5-is to see a mixture of 5 g (48 mmol) of ethyl ether aminouksusnoy acid (ethyl ester of glycine) and 4,96 g (49 mmol) of dry, fresh of triethylamine in 5 ml of abs. benzene and continue stirring 1 h at the same temperature, 1 h at 25-30oC and 1 h at 35-40oC. the precipitation is filtered off, the filtrate is evaporated to dryness in a water-jet pump vacuum and the dry residue was washed with water (350ml) and dried. Get 6,1 g (71 %) of 2-chloro-4,6-bis(ethoxycarbonylmethylene)-1,3,5-triazine (HAT) in the form of a white crystalline powder with so pl. 178-179oC.Found, %: C 41,71; N 5,19; N 22,18; Cl 12,05; C11H16N5lO4.Calculated, %: C 41,58; N 5,08; N 22,04; Cl Of 11.15.X , cm-1: 3250, 3180cf.(N-H); 1740c.(C=O); 1575, 1540C.,cf.,(C=C and C=N - comp.); 1240cf.(C-N); 1190, 1130cf.(C-O-C).PMR-spectrum , M. D.: 8,10ush.with.(2H, -N-H); 4,05...4,20m(4H, -CO2); 3,85...4,0m(4H,-NCH2); 1,20... 1,30m(6N,-CH3).Mol. ion 317 (mass.by a spectroscope).Through a solution of 5 g (16 mmol) received the HAT in 30 ml of abs. benzene in a stream of nitrogen, with stirring and a temperature of 101oWith bubbled dry trimethylamine. The saturation of trimethylamine continued for 1 h and the reaction mixture is stored at 20oWith 12 o'clock Formed abundant precipitate is filtered off, primarycare-4,6-bis (ethoxycarbonylmethylene)]-1,3,5-triazine (THAT) in the form of a white crystalline powder with so pl. 180-180,5oC.Found, %: C 44,73; N For 6.81; N 22,40; Cl At 9.53. WITH14H25N6lO4.Calculated, %: C 44,59; N 6,69; N 22,30; Cl 9,40.X , cm-1: 3435, 3225cf.(N-H); 1730c. (C=O); 1590, 1560, 1510C.,cf.C=C and C=N - comp.); 1190, 1150cf.(C-O-C).PMR-spectrum , M. D. : 8,12ush.with.(2H, N-H); 4,08...4,23m(4H, OCH2); a 3.87. . . 4,01m(4H, NCH2); 3,20m(N, N(CH3)3); 1,22... 1,31m(6N, -CH3).Example 2. Carried out under conditions analogous to example 1, from 5 g (16 mmol) HAT in 35 ml of abs. benzene, with the only difference that the bubbling dry trimethylamine continue for 1.5 h at 51oC, then incubated the reaction mixture at the 18oWith another 15 hours and get by 5.87 g (99%) [2-trimethylammoniumchloride-4,6-bis(ethoxycarbonylmethylene)]-1,3,5-triazine (THAT) in the form of a white crystalline powder with so pl. 180-180,5oC.Found, %: C 44,73; N For 6.81; N 22,40; Cl At 9.53. WITH14H25N6lO4.Calculated, %: C 44,59; N 6,69; N 22,30; Cl 9,40.X , cm-1: 3435, 3225cf.(N-H); 1730S.(C=O); 1590, 1560, 1510C.,cf.(C=C and C=N - comp.); 1190, 1150cf.(C-O-C).PMR-spectrum , M. D.: 8,12 ush.with.(2H, N-H); 4,08... 4,23m(4H, och
where About is the yield in the control and experimental variants, respectively.Examples 4-10 carry out strictly the same experience 3 way. For comparison, in similar conditions hold for the experience 8 use of the herbicide 2,4-D and its butyl ether, and as an antidote 1,2-dioxymethylene(prototype), experience 9 using to process only herbicide(standard) and control experience 10 - without the use of herbicide and antidote.All experimental Yes As can be seen from the data table.1, the application on the background of the impact of the herbicide 2,4-D proposed Quaternary salt: THAT as antidote provides in comparison with the standard increase in root length of seedlings of sunflower as at 31 - 44% (47-52 mm instead of 36 mm), while the use of known means 1,2-dioxymethylene provides an increase of only 19.4%. It is also clear that if as a result of fetotoksicheskoe steps reference (example 9) length of roots of seedlings is reduced in comparison with control by 45.5%, the use of the claimed THAT reduces fetotoksicheskoe herbicide action and length of roots decreased by 21.3-34,1%, while the use of known compounds prototype DMK reduces this rate is 34.9%.As can be seen from the data table.2, when used on the background of the impact of herbicide EB 2,4-D as an antidote to the claimed salt THAT productivity (yield) of sunflower seeds increased in comparison with the standard of 1.3 to 2.3 t/ha, or by 24.5 - 43,3%, compared to 6.6 and 7.6 t/ha instead of 5.3 t/ha), while the use of the known compounds of the prototype increases this figure only 16.9%. It is also clear that if as a result of fetotoksicheskoe steps reference (example 9) yields cf the IDA and the yield decreases only 54.5-60.5 per cent, while the use of known compounds prototype DMK reduces this figure by 62.9%.Thus, the use of the claimed compounds as the antidote allows for the impact of herbicide to increase the length of the roots of seedlings and productivity of seeds of sunflower plants (yield), and to simplify the technology of preparation and use working solutions. The Quaternary salt of 1,3,5-triazine of the formula
< / BR>which is the antidote from phyto-toxic action of the herbicide 2,4-dichlorophenoxyacetic acid and its butyl ether on the germinating seeds and vegetative plants of sunflower.
< / BR>The specified connection is a regulator of growth and development of plants and may find application in agriculture and horticulture
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
FIELD: agriculture, plant science, plant protection.
SUBSTANCE: the suggested herbicidal composition of selective action contains, except generally accepted additional substances for the composition, a mixture as an active substance including a) herbicidally efficient quantity of compound of formula (I) , where R1 and R3 each independently means ethyl, ethynyl, C1- or C2alkoxy; R4 and R5 forms together the group Z2-CR14(R15)-CR16(R17)-O-CR18(R19)-CR20(R21)-(Z2); R14, R15, R16, R17, R18, R19, R20 and R21 means hydrogen; G means hydrogen, -C(X1)-R30, -C(X2)-X3-R31; X1, X2, X3 means oxygen; R30, R31 each independently means C1-C10alkyl, or salts or diastereoisomer of compound of formula (I), and b) efficient quantity of antidote of formula IIa to prevent harmful action of herbicide, where R22 means hydrogen, alkaline-earth metal or ethyl, or of formula IIb , where R23 means hydrogen, alkaline-earth metal or ethyl, and method for selective control for weed plants and grasses in cultivated plants. Thus, the antidote decreases the damage of cultivated plants induced by herbicide of formula (I).
EFFECT: higher efficiency of plant protection.
3 cl, 4 ex, 4 tbl
FIELD: organic chemistry, agriculture.
SUBSTANCE: claimed mixture from herbicides and antidotes contains (A) herbicidically active substance based on phenylsulfonylureas of formula I and salts thereof (in formula R1 is hydrogen or C1-C6-alkyl; R2 is C1-C3-alkyl; R3 is C1-C3-alkoxy; R4 is hydrogen or C1-C4-alkyl; Hal is fluorine, chlorine, bromine, or iodine); and (B) antidote of formulae II or III , wherein X is hydrogen, halogen, C1-C4-alkyl; C1-C4-alkoxy, nitro or C1-C4-haloalkyl; Z is hydroxyl, C1-C8-alkoxy, C3-C6-cycloalkoxy, C2-C8-alkenyloxy, C2-C8-alkynyloxy; R5 is C1-C2-alkandiyl chain optionally substituted with one or two C1-C4 alkyl residues or (C1-C3-alcoxy)carbonyl; W is bivalent heterocyclic residue; n = 1-5; in weight ratio herbicide/antidote of 100:1-1:100. Also disclosed is method for protection of cultural plants against phytotoxic side effect of herbicidically active substance of formula I. Claimed method includes antidote application of formulae II or III on plant, plant parts, plant seeds or seeding areas before or together with herbicidically active substance in amount of 0.005-0.5 kg/hectare in weight ratio of 100:1-1:100.
EFFECT: mixture for effective selective weed controlling in cultural plant, particularly in maize and grain cultures.
8 cl, 2 ex, 7 tbl
FIELD: organic chemistry, agriculture, herbicide composition.
SUBSTANCE: invention relates to herbicide composition, containing conventional inert additives and mixture of a) herbicidically effective amount of substance satisfying the formula I [in formula R1 and R3 are the same or different C1-C4-alkyl; R4 and R5 together form groups of formulae: -C-R6(R7)-O-C-R8(R9)-C-R10(R11)-C-R12(R13)-(Z1), -C-R14(R15)-C-R16(R17)-O-C-R18(R19)-C-R20(R21)-(Z2), or -C-R22(R23)-C-R24(R25)-C-R26(R27)-O-C-R28(R29)-(Z3), wherein each R6-R29 is hydrogen; G is hydrogen or -C(X2)-X3-R31; X2 and X3 independently are oxygen; R31 is C1-C10-alkyl]; b) herbicidic synergic amount of at least one herbicide selected from group containing sulfonylureas, phenoxyacetic acids, as well as florsulam, tralcoxidim, klodinafol-propargil, phenoxaprop-P-ethyl, trifluramine, pendimethaline, picolinafen, etc. Composition also may contain safety effective amount of protective agent, such as chloquintocet-mexyl and additive (e.g., mineral oil or C8-C22-fat acid alkyl esters) in amount of 0-2 mass %. Also disclosed is method for selective controlling of weeds and grassy plants in cultural plants by treatment of cultural plants, seeds or seedlings thereof, or vegetation area thereof with claimed composition.
EFFECT: effective composition and method for weed controlling.
5 cl, 11 tbl, 7 ex
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