• 专利附录
  • 专利说明
  • 权利要求
  • 类似技术
  • 同族专利
  • 引用文献
  • 法律状态
  • 优先权
    • 专利摘要:
    This invention relates to chemical plant protection products, in particular, to chemical agents that reduce the phototoxic effect of herbicides on cultivated plants. The purpose of the invention is to reduce maize damage by thiocarbamate herbicides. According to the invention, a thiocarbamate herbicide based composition contains an antidote based on 0.048-1.66 hours per 1 hour herbicide. As an antidote, compounds of the general formula R 1 R 2 CXR 3 (YR 4 ) are used, where XO or N-phenyl, N-chlorophenyl Y — O, N-phenyl, N-2,6-dimethylphenyl R 1 is hydrogen, dichloromethyl, bromomethyl, chloromethyl, trichloromethyl R 2 is hydrogen, dichloromethyl R 3 and R 4 are each C 1 -C 5 , C 8 -C 18 -alkyl, allyl, benzyl, tetrahydrofuryl, furyl, 2-chloroethyl, dimethylaminoethyl or R 3 and R 4 together bis-methylene, 2-ethylethylene, methylethyl, Methylpropylene, glycofuraniline. Anhydrates according to the invention at a lower dose provide an equal or higher level of protection for maize against the toxic effects of thiocarbamate herbicides. 5 tab.
    公开号:SU1478990A3
    申请号:SU813364702
    申请日:1981-12-10
    公开日:1989-05-07
    发明作者:Дутка Ференц；Кемивеш Тамаш；Фодор Каталин；Мартон Аттила；Чикош Анико；Остхаймер Ева；Хенгер Карой；Лаборци Роберт；Рети Жужанна；Шебек Деже；Саболч Йожеф；Темерди Элемер
    申请人:Мадьяр Тудоманьош Академиа Кезпонти Кемиаи Кутато Интезете (Инопредприятие)；Нитрокемиа Ипартелепек Фюзфедьяртелеп (Инопредприятие)；
    IPC主号:
    专利说明:

    one
    The invention relates to chemical plant protection products, in particular to agents that reduce the toxicity of herbicides to cultivated plants, and can be used in plant growing.
    The purpose of the invention is to reduce the degree of maize damage by thiocarbamate herbicides.
    Spreadable composition as an antidote contains a compound of the general "formula
    Bixc.XR3 (C
    R2 YH4
    The composition is used to relieve the toxic effect of thiocarbamate herbicides such as EPTC (8-ethyl-I, N-di-n-propylthiocarbamate), butylate (B-ethyl CHI
    NjN-diisobutylthiocarbamate, vernol-ta (8-n-propyl-M, N-di-n-propylthiocarbamate), pebulate (Sn-propyl-n-butyl-K-ethylthiocarbamate), molinata (8 ethyl-M , N-hexamethylene thiocarbamate), cycloate (3-ethyl-K-ethyl-M-cyclohexylthiocarbamate), diallate (8-2,3-dichloroyl-N, 1 1-diisopropylthiocarbamate), as well as carbamates of the type 4-chloro-2-butynyl- (3-chlorophenyl) - carbamate drum, amides of the acetochlor type (2-ethyl-6-methyl-K-ethoxymethylchloroacetanilide), alachlor (2,6-diethyl-M-methoxymethylchloroacetanilide), metol - chlorine b ethyl-2-methyl-I- (2-methoxy-1-methylethyl) -chloroacetanilide and p of urea derivatives of the linuron type 3- (3,4-dichlorophenyl) -1-methoxy-1-methyl-urea. Regardless of the mechanism of action in each individual case, the advantage of the proposed derivatives of aldehydes and ketones is that they reduce or eliminate the harmful effect of herbicides on healthy crops, without reducing their action on weed control.
    The synthesis of compounds of general formula (I) is carried out as follows.
    Oxidation of the general formula
    R2
    (Ii)
    where R and Ri have the same meanings as in the compound of general formula (I), are mixed with the corresponding mono- or dihydric alcohol, thiol, amine or thio-alcohol, amino alcohol or aminothiol in benzene in the stoichiometric ratio and boil at reflux for several hours (4-11 hours). The resulting water is removed from the system during the whole process (using a Dean-Stark nozzle). In the preparation of derivatives containing oxygen or sulfur or oxygen and sulfur, 4-methylbenzosulfonic acid is used as a catalyst. The reaction product is separated depending on its nature by filtration or distillation.
    Compounds of general formula (I) containing oxygen or sulfur or oxygen and sulfur are prepared as follows. The compound of the general formula
    R2
    Ri-C-OR (and;
    (W
    where R and R4 are the same as in the
    the general formula (I); R and R, which are the same or different alkyl groups with 1-4 carbon atoms, are reacted with an appropriate mono- or dihydric alcohol, thiol, or thio-alcohol in the presence of a catalyst, for example, 4-methylbenzosulfonic acid, at reflux temperature. Isolation of the product is carried out as described.
    Example 1. Preparation of diethyl acetal dichloroacetaldehyde.
    896% ethanol, maintained at 25 ° C, passes chlorine gas until two phases form. The organic phase is dried over calcium carbonate, then distilled.
    Bp 107-108 ° C (38 mmHg).
    Example 2. Preparation of dimethyl acetal dichloroacetaldehyde.
    A mixture of 8 g of diethyl acetal dichloroacetaldehyde, 30 ml of methanol and 0.1 g of 4-methylbenzenesulfonic acid is kept at reflux for 5 hours, then distilled. Bp 167-168 S.
    Example 3. Preparation of trichloroacetaldehyde diisoamylacetal.
    A mixture of 5 g of chloral hydrate, 10 g of eoamyl alcohol, 0.1 g of 4-methyl-. benzosulfonic acids and 50 ml of benzene are maintained at reflux temperature and the water formed is separated using a Dean-Stark apparatus. After 9 hours of reaction, the benzene solution is washed with a solution of sodium bicarbonate and water, dried over magnesium sulphate and distilled under vacuum; 4 ° 1.4519.
    Example 4. Preparation of trichloroacetaldehyde dibutyl acetal.
    B, a device equipped with a Dean-Stark water separator, is placed 7 g of chloro-aldehyde, 10 g of butyl alcohol, 0.1 g of 4-methylbenzenesulfonic acid and 50 ml of benzene. When heated in a water bath, the zodine is distilled off for 10 hours. The benzene solution is washed with sodium bicarbonate solution and water and the benzene is distilled off. The product is distilled under vacuum. Bp (3 mm Hg).
    PRI me R. 5. Getting 2-di. chloromethyl-1,3-dioxane.
    9 g of dichloroacetaldehyde diethyl acetal and 5 g of propylene glycol in the presence of, 0.1 g of 4-toluenesulfonic acid are heated for 44 hours in a water bath. The product is purified by vacuum distillation in the presence of 0.3 g of potassium carbonate. T. Kip. 78 - (15 mm Hg).
    Example 6. Preparation of diethyl acetal bromoacetaldehyde.
    To a mixture of 10 g of vinyl acetate and 20 ml
    carbon tetrachloride with cooling (10 ° C) is added and solution 10 is filtered. M.p.
    After 7 hours at a temperature of fl, the water is separated and the Dean-Stark nozzles are separated. Ras 5 is distilled off, the residue is kept at 60 ° C. The precipitated material is adjusted and the pH of the mother liquor is adjusted to 6.5 sodium hydroxide. Separating
    183 ° C.
    18.5 g of bromine in 10 ml of carbon tetrachloride. 60 ml of ethanol is added to the mixture and allowed to stand for 2 days. The organic phase is washed twice with 50 ml of water and then distilled under vacuum. Bp 59-6l ° C (15 mmHg).
    Example 7. Preparation of dipropyl acetal dichloroacetaldehyde.
    dock filtered out. M.p.
    7 hours at reflux temperature and the water formed is separated using a Dean-Stark apparatus. The solvent is distilled off, the residue is kept at 60 ° C for 20 minutes. The precipitated substance is filtered off and the pH of the mother liquor is adjusted to 6.5 using sodium hydroxide. The separated wasp 182 is filtered off. M.p.
    183 ° C.
    Example 13. Preparation of 2- (dichloromethyl) -2-methyl-1,3-dioxolane.
    A mixture of 4.5 g of 1,1-dichloroacetone, 3.7 ml of ethylene glycol, 0.1 g of 4-methyl-
    benzenesulfonic acid and 30 ml of benzene are kept at reflux for 9 hours, while water is gradually separated. The reaction mixture is washed
    A mixture of 5 g of diethyl acetal dichloroacetic sodium bicarbonate solution, desiccated aldehyde, 30 ml of propanol and 0.1 g of 4-methylbenzenesulfonic acid is heated for 5 hours in a water bath, then distilled. Bp 21Q-211 ° C.
    Example 8. Obtaining 2-di chloromethyl-1,3-dioxolane.
    10 g of dichloroacetaldehyde diethyl acetal and 3 g of ethylene glycol in the presence of 0.1 g of 4-methylbenzenesulfonic acid are taken up over magnesium sulfate and distilled. Bp 92-94 ° C (27 mmHg). Example 14. Preparation of 2-dichloromethyl-2-methyl-1,3-dioxolane. 25 8.0 g of 1,1-dichloroacetone 6.7 ml of ethylene glycol is treated in the presence of p-toluenesulfonic acid — a catalyst in a system for separating water.
    or, using a molecular sieve, is heated for 5 hours in a water bath; 30 (4 A) is a binder for water and then
    the product is distilled under vacuum. Bp 187 ° C.
    Example 9. Preparation of 2-trichloromethyl-1,3-diphenylimidazoline.
    To 7 g of N, N-diphenylethylenediamine 35 add 40 ml of acetic acid, then 30 g of chloral. The mixture is left to stand for 72 hours, then the separated solid is filtered off. Bp 136-137 ° С.40
    Example 10. Preparation of dioctylacetal dichloroacetaldehyde.
    A mixture of 5 g of diethyl acetal dichloroacetaldehyde, 25 g of octanol and 0.1 g of 45 4-methylbenzenesulfonic acid is heated for 5 hours in a water bath, then distilled; 0 1.4 6 27.
    Example 11. Preparation of 2,2,2-trichloro-1-allyloxyethanol. 50
    A mixture of 7 g of chloral, 2.9 g of allyl alcohol and 15 ml of benzene is kept overnight at room temperature, then distilled; 1.4820.
    distilled on a Vigre column. Q.93 94 C (2 mm Hg). The 1,1-dichloro-acetone used as starting material is prepared as follows. To 14.5 g of acetone placed in a round-bottomed flask equipped with an addition funnel, a stirrer and a reflux condenser with a CaCl g tube, while cooling, 67.5 g of sulphuryl chloride are added dropwise at a rate such that the temperature in the system does not exceed 30 -40 C; after reacting for 3-5 hours, excess reagent is removed by distillation. Bp 117-118 ° C.
    Example 15. Preparation of 2-dichloromethyl-3-phenyl-1,3-oxazolidine.
    In a flask equipped with a nozzle for separating water, 6.86 g of N-phenylethanol amine is treated with 5.6 g of dichloroacetaldehyde in a benzene medium to separate the calculated amount of water. A molecular sieve can also be used to bind water. Benzene is removed in a rotating vacuum. Example 12. Preparation of pi-evaporator, the residue is purified by chromatorosis by means of column chromatography or distillation. AT
    A mixture of 4.5 g of glucose, 19 g of chloral, a case of chromatography on a column of 20 ml of chloroform and 0.05 g of a 4-methylben-mixture on silica gel 60
    The sol-sulfonic acids are incubated (Merck, 70-230 mesh), the filling is forged over magnesium sulfate and distilled. Bp 92-94 ° C (27 mmHg). Example 14. Preparation of 2-dichloromethyl-2-methyl-1,3-dioxolane. 8.0 g of 1,1-dichloroacetone is treated with 6.7 ml of ethylene glycol in the presence of p-toluenesulfonic acid – catalyst in a water separation system.
    distilled on a Vigre column. Tyr.93-94 C (2 mm Hg). The 1,1-dichloro-acetone used as starting material is prepared as follows. To 14.5 g of acetone placed in a round-bottomed flask equipped with an addition funnel, a stirrer and a reflux condenser with a CaCl g tube, while cooling, 67.5 g of sulphuryl chloride are added dropwise at a rate such that the temperature in the system does not exceed 30 -40 C; after reacting for 3-5 hours, excess reagent is removed by distillation. Bp 117-118 ° C.
    Example 15. Preparation of 2-dichloromethyl-3-phenyl-1,3-oxazolidine.
    In a flask equipped with a nozzle for separating water, 6.86 g of N-phenylethanol amine is treated with 5.6 g of dichloroacetaldehyde in a benzene medium to separate the calculated amount of water. A molecular sieve can also be used to bind water. The benzene is removed in a rotating wafer, eluted with a mixture of benzene: ethyl acetate in a ratio of 12: 5. Bp (0.4 mm Hg); 1.5890.
    The N-phenylethanolamine used as the starting material was prepared as follows. 4.39 g of aniline are treated with 3.2 ml of ethylene chlorohydrin in the presence of 4.61 g of Na4CO3 as an acid binding agent for 3 to 4 hours at the boiling point of ethylene chlorohydrin. The residue is filtered, washed with benzene and, after removal of the solvent, is distilled under vacuum. Bp 182-188 ° C (30 mmHg).
    By these methods, compounds of the general formula (I) are obtained from the corresponding starting materials, which can be used as antidotes in the proposed herbicidal compositions.
    The structure and properties of the proposed compounds are presented in table.1.
    The proposed antidotes or formulations containing them can be obtained and applied in any form. Thus, if necessary, emulsifying liquids, emulsifiable concentrates, wettable powders or granular preparations can be prepared. As herbicides such as tnocarbamates are advisable as biologically active substances. The preparation contains a biologically active substance
    an antidote, it is possible to sow the seeds to be sown before or after sowing or treating with the preparation. It is possible to recycle the herbicide biologically active substance and the proposed protective agent, in each case separately, with an appropriate liquid or solid carrier to obtain a preparation suitable for tillage, seed or planting. The preparations are successively applied to the soil or applied to the grain or plants to be treated. The proposed antidote can be applied to the seeds, and the herbicidal biological agent can be applied to the soil before or after sowing.
    The proposed antidotes can be used together with herbicidal biologically active substances that contain herbicidal thiocarbamate carbamates, amides, acids, urea derivatives in particular or in any combination. Herbio 5
    0
    50
    five
    about 5 n
    -to
    The cid activity of biologically active substances or combinations may vary and depends on the type of plant for which the appropriate individual herbicidal compound is used or in a mixture with other herbicidal compounds.
    Through the use of the proposed antidote, one can avoid the harmful impact of vi-1 on cultivated plants of herbicidal biologically active substances or combinations of biologically active substances.
    The effect of the proposed drugs is tested by seed or soil treatment methods. At the same time, 6 seeds of useful crops and 15 seeds of weeds are placed in the soil, prepared depending on the specified types of treatment, placed in containers-from plastic, 10x1x in size. The effectiveness of the antidote for several herbicides or useful crops and weeds is tested, while the humidity of the air, light and temperature are regulated.
    Tests with seed treatment.
    10 g of seeds are shaken with 50 mg of the proposed antidote of a well-closed, ground container until the seeds are evenly coated with the substance. The application of the compounds to the seeds can be accelerated by adding acetone. The seeds treated in this manner are introduced into the soil in the indicated containers, into which the herbicidal biologically active substance is previously uniformly applied so that in the mixing device a certain amount of the herbicidal biologically active substance is added to the soil herbicide solution (herbicides).
    Seeds are placed in prepared soil to a depth of 2.5 cm. The soil in the tank is watered so as to ensure favorable growth of the plants.
    Damage to maize in the case of seeds treated with 0.5% of antidote (A) or untreated (B) is given in Table 2.
    Tests with soil treatment.
    The proposed composition containing a herbicidal biologically active substance and antidote, evenly mixed with the soil in such a way that
    To the soil in the mixing tank, add a certain amount of a suitable established stock solution of the herbicide (s) and the antidote to be tested.
    In the soil prepared in this way and placed in containers for experiments to a depth of 2.5 cm, the seeds of the test grass and broad-leaved useful crops are introduced. The soil in the tank is watered so as to ensure favorable development of the plant.
    The data on the protective effect of antidotes against herbicide damage to maize is presented in Table 3.
    The results of the effect of antidote 1 on reducing damage caused by thiocarbamate herbicides (expressed
    权利要求:
    Claims (1)
    [1]
    Invention Formula
    A herbicidal antidote composition comprising a thiocarbamate herbicide and an antidote, characterized in that, in order to reduce the damage to maize, it contains as an antidote a compound with an oral formula 1
    ks / -
    15 ъ / NR,
    . where with X and Y is oxygen each R is dichloromethyl; R2 is hydrogen; R and R4 - together bismethylene, trimethylene, TatraI
    by changing the height of plants by cara- 20 methylene, 1 - methyl propylene, ethylethylene or R3 and Rq. each is methyl, ethyl, amyl, octyl, octadecyl, allyl, cyclopentyl, benzyl, 2-chloroethyl, 2-methoxybutyl, dimethylaminoethyl, fur25 FURYL, tetrahydrofurfuryl, or RJ, methyl R and R together - bismethylene, methyl ethylene, R is chloromethyl and Ra is hydrogen R, “R each is C4-Cc-alkyl, or when R is bromomethyl,
    30 Ra В ° Д ° Р ° Д R) and R + each is ethyl} with X is oxygen and Y is N-phenyl, N is propyl, N is 2,6-dimethylphenyl R, methylene chloride; R is hydrogen; R3 and R together - bismethylene or at X
    3 and Y each is N-phenyl, R, is methylene chloride, R4 is hydrogen and R5 and R. instead is bismethylene, in a ratio of herbicide: antidote, equal to 1: 0.048 - 1.66.
    with untreated control group), maize (hybrid variety Pioneer 3950) on sandy soils 21 days after treatment are presented in Table 4.
    Data on the antidote activity of the proposed compounds, expressed in the change in plant height relative to the control of EPIC (M), are given in Table 5.
    The studies were performed on a sand culture, a mixture of herbicide with antidote was applied to the soil.
    Thus, by applying the proposed composition, it is possible to avoid the harmful effects on crop plants of herbicidally active substances,
    Invention Formula
    A herbicidal antidote composition comprising a thiocarbamate herbicide and an antidote, characterized in that, in order to reduce the damage to maize, it contains as an antidote compound with Formula One
    ks / -
    ъ / nr,
    where with X and Y is oxygen each R is dichloromethyl; R2 is hydrogen; R and R4 - together bismethylene, trimethylene, Tatra a b l and c a2
    .
    Significantly different from the control group at the 5% level.
    91 70 71
    .
    §-§.
    103 101 100
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