Fungicidal composition
专利摘要:
FUNGICIDE MEANS in the form of an emulsifiable concentrate, containing the active ingredient - a derivative of 1,2,4-triazol-1-ylbutanol-2, the solvent - dimethylformamide and emulsifier-alkylaryl polyglygly ethereal, which is, in fact, in order to increase its fungicidal activity, it contains 1,2,4-triazol-1-ylbutanol-2 as a derivative of a general formula- .. HE (JH, B-H-CH-C-iJHjY CHOX I It K- where R - butyl, cyclopropylmethyl, benzyl, 2-chloro-E-chloro, 4-chloro, 2,4-dichloro, 3,4-dichloro, 2,6-dichloro, 2-fluoro, 4-fluoro ; 4-bromo, 4-chloro-3.-trifluoromethyl, 4-methyl 4-trif ormethyl, 4-nitro, 4-cyanobenzyl X - hydrogen, fluorine; Y - fluorine, chlorine, and X can be fluorine, if Y is fluorine, and as alkylaryl polyglycol ether nonylphenol polyglycol ether, containing an average of 18 alcohols on 18 molecule, with the following ratio of components, May, h,: Derivatives 1, 2,4-triazol-: -.1-ylbutanol-2 decree of a different formula 0.25 Dimethylformamide 25.00 Nonylphenol polyglycol ether,. containing an average of 18 alcohol groups per molecule 0.06 公开号:SU1072787A3 申请号:SU803215945 申请日:1980-12-11 公开日:1984-02-07 发明作者:Крэмер Вольфганг;Гейнц Бюхель Карл;Эрнст Фробергер Пауль;Брандес Вильгельм;Люрссен Клаус 申请人:Байер Аг (Фирма); IPC主号:
专利说明:
The invention relates to chemical plant protection agents, specifically, to a fungicidal agent in the form of an emulsifiable concentrate based on 1,2,4-triazol-1-butyl-2-derivatives. Known fungicidal agent based on 1,2,4-triazole derivatives pz. The closest to the present invention is a fungicidal agent based on a derivative of 1,2,4-triazole-1-butyl-2-dimethylformamide and alkyl aryl polyglycolic ether G23. . However, these fungicidal agents have insufficient activity at low concentrations. The purpose of the invention is to increase the fungicidal activity of the agent. This goal is achieved in that the fungicidal agent in the form of an emulsifiable concentrate containing the active ingredient contains 1,2, triazole-1-ylbutanol-2 as a derivative, a compound of the general formula HE CH3 (1) B-CH-W-CH I CH2X vO to- where R is butyl, cyclopropylmethyl, benzyl, 2-chloro, 3-chloro, 4-chloro, 2,4-dichloro, 3,4-dICHLOR7 2,6-dichloro, 2-fluoro, 4- f, tor-, 4-bromo-, 4-chloro-: 3-trifluoromethyl 7 4-methyl 4-trifluoromethyl 4-nitro, 4-cyanobenzyl j X is hydrogen, fluorine; Y is fluorine, chlorine, and X can to be fluorine if y is fluorine, and as nonyl Lenol polyglycol ether as alkylaryl polyglycol ether, containing an average of 18 alcohol groups per molecule, with the following ratio of components, wt. Derived 1,2,4-triazole-1ylbutanol-2 specified form0, 25 ly 25.00 , Dimethylformamide Nonylphenol polyglycol ether, containing on average 18 alcohol 0.06 groups per molecule. The proposed agent is prepared by simple mixing of the components. Compounds (I) are obtained by reducing the corresponding ketones, which are carried out by reacting with complex hydrides, if necessary in the presence of a diluent, or by reacting with aluminum isopropoxide in the presence of a diluent, or by reacting with hydrogen in the presence of a catalyst and, if necessary. diluent When using complex hydrides as a diluent, polar organic solvents, preferably methanol, ethanol, butanol, isopropanol, diethyl ether, tetrahydroFuran, are suitable for reaction. The reaction is carried out at 0-30, preferably at. Apply per mole of ketone to approximately 1 mole of a complex hydride, such as sodium borane or lithium alanate. In order to obtain the reduced compounds of the formula (I), the residue is taken up in a dilute roll acid, then alkalinized and extracted with an organic solvent. Recycle in the usual way. In the case of using aluminum isopropyl as a diluent for the reaction, preferably spiters, such as isopropanol or inert hydrocarbons, such as benzene, are suitable. The reaction temperature is 20-120 s (preferably 50 LU s). Approximately 1-2 mol of aluminum isopropylate are used per mole of ketone for the reaction. To isolate the recovered compounds of formula (I), excess solvent is removed by vacuum distillation and the resulting aluminum compound is decomposed with dilute sulfuric acid or sodium hydroxide. Recycle in the usual way. In the case of using hydrogen as a diluent, polar organic solvents, preferably methanol and ethanol, acetonitrile, are suitable for the reaction. The reaction is carried out in the presence of a catalyst; preferably, noble metal catalysts, noble metal oxides or noble metal hydroxides, or so-called Rene catalysts, in particular platinum, platinum oxide and nickel, are preferably used. Reaction temperature 20-50С. The reaction can be carried out at normal or elevated pressure, for example 12 MPa. For the reaction, about 1 mole of hydrogen and 0.1 mole of catalyst are used per mole of ketone. To isolate the reduced compounds (I) thereof. filtered from the catalyst and freed from the solvent in vacuo. Recycle in the usual way. The compounds obtained by the proposed method are listed in Table 1. Table 1 CHj c-en2 Example 1. A barley plant (Amsel variety) with 1 leaf is sprayed with an aqueous fungicide preparation consisting of parts by weight: active ingredient 0.25, dimethylformamide 25 and nonylphenol polyglycol ether 0.06, containing an average of 18 alcohol groups on the molecule. After suspending, the plants are barren with spores of Egusiphe graminls var.hordei .. After. 6 days of plant storage at 21-22 s and 80-90% air humidity determine the defeat of plants by powdery mildew pustules. The extent of the damage is determined as a percentage of the damage to the untreated control plants. At the same time, 0% means no damage, and 100% means the same degree of damage as that of untreated control plants. The active substances and the results of the experiment are summarized in table. 2. Table Damage {%) during the concentration of active substances in a preparation, O, 001% (known) (known) is neo-Synthesis of Actual Thing (from (from (that the damage is the same as in treated plants). Active substances the means and results of the experiment are given in Table 3. Table 3 Defeat () at the end of the active substance in the preparation is 0.00025% known) Known Vneshtnoe / Example 2. Young barley plants are sprayed to form droplets with an aqueous fungicide preparation consisting of parts by weight: active substance O, 25, dimethylformamide 25 and nonIlphenol polyglycol ether 0.06, containing on average 18 alcohol groups per molecule. After drying, the plants are sprayed with spores of Erysiphe graminis f.sp, hordei. Plants are stored in a greenhouse at 20 s and a relative humidity of 80% for 7. days Then the degree of damage (in%) of the untreated control plants is determined. In this case, 0% no damage, and -100% means Example 3. Young plants are sprayed before dropping an aqueous fungicide preparation consisting of parts by weight active substance 0,25 ,. dimethylformamide 25 and nonylphenol polyglycol ether 0.06, containing an average of 18 alcohol groups per molecule. After drying, the plants are sprayed with spores of the fungus Sphaerotheca fuliginea. The plants are then stored in a greenhouse at 23-24 ° C and a relative air humidity of 75% for 10 days, after which the extent of damage (in%) from untreated control plants is determined. At the same time, 0% - no lesion, and 100% means that the lesion is the same as that of untreated control plants. The active substances and the results are shown in table 4. Table 50 46 41 12 2 12 19 16 8 Continued table. four --ia. 2 7 12 12 34 25 25 16 12 12 25 21 eight 9 1011 12 13 14 15 16 25 Thus, the proposed agent has a high fungicidal activity at low concentrations.
权利要求:
Claims (2) [1] FUNGICIDIC AGENT in the form of an emulsifiable concentrate containing the active ingredient - a derivative of 1,2,4-triazol-1-ylbutanol-2, the solvent is. dimethylformamide and emulsifier-alkylaryl polyglycol ether. It is different from the fact that, in order to increase the fungicidal activity, it contains isola-2 mules. as a pro 1,2,4-triazol-1-yl buso compound of general form OH CH 3 II 4 n — J where R is butyl, cyclopropylmethyl. Benzyl, 2-chloro-3-chloro, 4-chloro, [2] 2,4-dichloro-, 3, -4.-dichloro-, 2,6-dichloro-, 2-fluoro-, 4-fluoro-4-bromo, 4-chloro-3-trifluoromethyl, 4-methyl; 4-trifluoromethyl, 4-nitro, 4-cyanobenzyl; X is hydrogen, fluorine; Y is fluorine, chlorine, wherein X may be fluorine if Y is fluorine and nonylphenol polyglycol as alkylaryl polyglycol ether. ether containing an average of 18 alcohol groups per molecule, in the following ratio of components, wt.h .: derivatives 1,2,4-triazol-1-ylbutanol-2 of the indicated formula Dimethylformamide Nonylphenol polyglycol ether containing on average 18 alcohol groups per molecule M , _SU m , 1072787 0.25 25.00 0.06
类似技术:
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引用文献:
公开号 | 申请日 | 公开日 | 申请人 | 专利标题 DE2431407C2|1974-06-29|1982-12-02|Bayer Ag, 5090 Leverkusen|1,2,4-Triazol-1-yl-alkanones and alkanols, processes for their preparation and their use as fungicides| GB1533375A|1976-07-20|1978-11-22|Bayer Ag|Halogenated 1-azolyl-butane derivatives and their use as fungicides| BR7705001A|1976-07-29|1978-05-02|Ici Ltd|COMPOSITION TO COMBAT FUNGI AND PROCESS TO COMBAT DISEASES CAUSED BY FUNGI| IE45765B1|1976-08-19|1982-11-17|Ici Ltd|Triazoles and imidazoles useful as plant fungicides and growth regulating agents| DE2811919A1|1978-03-18|1979-09-27|Bayer Ag|ACYLATED 1-AZOLYL-2-HYDROXY-BUTANE DERIVATIVES, METHODS FOR THE PRODUCTION THEREOF AND THEIR USE AS FUNGICIDES| EP0015639A3|1979-02-09|1980-10-01|Imperial Chemical Industries Plc|Enantiomers of triazole compounds, a process for preparing them, their use as plant fungicides and growth regulating agents and compositions containing them| DE2905981A1|1979-02-16|1980-10-30|Bayer Ag|1-ALLYLTRIAZOLE DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS A PLANT PROTECTION PRODUCT| DE2951163A1|1979-12-19|1981-07-16|Bayer Ag, 5090 Leverkusen|SUBSTITUTED TRIAZOLYL METHYL-TERT.-BUTYL-CARBINOLE, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS A PLANT PROTECTION AGENT AND AS AN INTERMEDIATE PRODUCT|DE2951163A1|1979-12-19|1981-07-16|Bayer Ag, 5090 Leverkusen|SUBSTITUTED TRIAZOLYL METHYL-TERT.-BUTYL-CARBINOLE, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS A PLANT PROTECTION AGENT AND AS AN INTERMEDIATE PRODUCT| DE3048267A1|1980-12-20|1982-07-15|Bayer Ag, 5090 Leverkusen|SUBSTITUTED 1-AZOLYL-BUTANE-2-OLE, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS A PLANT PROTECTANT AND AS AN INTERMEDIATE PRODUCT| DE3209431A1|1982-03-16|1983-09-22|Bayer Ag, 5090 Leverkusen|PHENOXYPROPYLTRIAZOLYL KETONES AND CARBINOLS, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS FUNGICIDES| DE3222191A1|1982-06-12|1983-12-15|Bayer Ag, 5090 Leverkusen|HYDROXYALKINYL-AZOLYL DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS FUNGICIDES| DE3224129A1|1982-06-29|1983-12-29|Bayer Ag, 5090 Leverkusen|SUBSTITUTED AZOLYL KETONES AND ALCOHOLS| DE3234627A1|1982-09-18|1984-03-22|Bayer Ag, 5090 Leverkusen|SUBSTITUTED AZOLYLALKYL T-BUTYL KETONES AND CARBINOLS| PH19347A|1982-09-30|1986-04-02|Pfizer|Triazole derivatives,pharmaceutical composition containing same and method of use thereof| DE3242222A1|1982-11-15|1984-05-17|Bayer Ag, 5090 Leverkusen|HYDROXYALKINYL-AZOLYL DERIVATIVES| CN1008735B|1984-11-02|1990-07-11|拜尔公司|Pyrrole ylmethyl-cyclopropyl-carbinol derivatives with replacement is a composition of active components| GB2184113B|1985-08-07|1989-08-23|Ici Plc|Heterocyclic compounds| IT1186784B|1985-11-04|1987-12-16|Montedison Spa|AZOLIDERIVATED ANTI-FUNGAL ACTIVITIES| US4895865A|1986-01-10|1990-01-23|Rohm And Haas Company|Alpha--alpha-alkyl-1H-1,2,4-triazole-1-propanenitriles and derivatives| GB8603951D0|1986-02-18|1986-03-26|Ici Plc|Heterocyclic compounds| DE3720756A1|1987-06-24|1989-01-05|Bayer Ag|AZOLYL METHYL CYCLOPROPYL CARBINOL DERIVATIVES| DE3834437A1|1988-10-10|1990-04-12|Basf Ag|AZOLYLMETHYLCYCLOPROPANE AND THEIR USE AS A PLANT PROTECTANT| DE3923151A1|1989-07-13|1991-01-24|Basf Ag|1,2-DIHALOGENAZOLYLETHANE DERIVATIVES AND PLANT PROTECTION PRODUCTS CONTAINING THEM| DE4025204A1|1990-08-09|1992-02-13|Bayer Ag|HALOGENALKYL-AZOLYL DERIVATIVES| US5262434A|1990-08-09|1993-11-16|Bayer Aktiengesellschaft|Halogenoalkyl-azolyl derivatives| CN102659696B|2012-05-04|2014-07-16|北京颖泰嘉和生物科技有限公司|Method for improving anti-caking property of tebuconazole| CN106397346B|2016-08-31|2018-12-07|黑龙江八一农垦大学|1- -base -3,3- dimethyl-2-butanone and its application|
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申请号 | 申请日 | 专利标题 DE19792951163|DE2951163A1|1979-12-19|1979-12-19|SUBSTITUTED TRIAZOLYL METHYL-TERT.-BUTYL-CARBINOLE, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS A PLANT PROTECTION AGENT AND AS AN INTERMEDIATE PRODUCT| 相关专利
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