![]() Method of plant fungic disease control
专利摘要:
1425621 Fungicidal application of cyano substituted acetamide derivatives EI DU PONT DE NEMOURS & CO 15 March 1973 [15 March 1972 7 Feb 1973] 12458/73 Heading A5E A composition for combating fungus disease in plants comprises an inert diluent and a compound of the general formula: wherein R is hydrogen; alkyl of 1 to 13 carbon atoms; alkyl of 1 to 13 carbon atoms substituted with alkoxycarbonyl of 2 to 4 carbon atoms, acyl of 2 to 4 carbon atoms. acyloxy of 2 to 4 carbon atoms or cyano: acyl of 1 to 4 carbon atoms; alkoxycarbonyl of 2 to 4 carbon atoms; aralkyl of 7 to 10 carbon atoms; or a non-phytotoxtic metal; R, is alkoxy of 1 to 4 carbon atoms or -NR2R3; R2 is hydrogen, alkyl of 1 to 4 carbon atoms, alkoxycarbonyl of 2 to 4 carbon atoms or R3 is hydrogen or alkyl of 1 to 4 carbon atoms with the proviso that R3 is H when R2 is alkoxycarbonyl or formula III shown above R4 is hydrogen or alkyl of 1 to 4 carbon atoms; R5 is hydrogen or alkyl of 1 to 4 carbon atoms; and X is oxygen or sulfur; with the proviso that when R<2> is hydrogen, alkyl or alkoxycarbonyl, said composition is not a simple solution of said compound in water or an organic solvent. Typical compounds used are 2-cyano-2-hydroxyiminoacetamide, 2-cyano-2-methoxyiminoacetamide, N- carbamoyl-2-cyano-2-methoxyacetamide, 2-acetoxyimino-2-cyano-N-methyl acetamide, and N- (methyl - carbamoyl) -2-cyano-2-methoxyimino acetamide. Optional composition ingredients are surfactants, film forming polymers, humectants, non-phytotoxic oils, insecticides, miticides, bactericides, nematicides, fruit-set agents, fruit thinning compounds, fertilizers and other fungicides (especially benomyl, maneb, captafol, metiram, chlorothalonil, daconil and zineb). 公开号:SU736856A3 申请号:SU731890161 申请日:1973-03-14 公开日:1980-05-25 发明作者:Хэйес Дэвидсон Сидней 申请人:Е.И.Дюпон Де Немур Энд Компани (Фирма); IPC主号:
专利说明:
one The invention relates to chemical plant protection agents, specifically, to a method of controlling fungal plant diseases by treating them or their biotope with oxime derivatives. A fungicide is known, the active substance of which is the manganese ethylene bis-dithiocarbamic acid salt (maneb) 1. It is also known that oxime derivatives, for example, 1-cyano-O-carbomoylformaxim 2, N-aryl-substituted oxime carbamates exhibit pesticidal activity 3. However, the activity of these compounds at low doses of the drug consumption is insufficient. The aim of the invention is to find a new method of controlling fungal diseases of plants with enhanced efficiency. / This is achieved by treating them or their biotope with an active substance of the formula S "(f (1) R — O — N — C — C — R 2 where r hydrogen, alkyl s, acyl containing 2-4 carbon atoms, ethylacetate, etiloxy, alkoxy, Icarbonylmethyl methyl cyano, propyl cyano, hexyl cyano, alkylenephenyl, a metal selected from the group consisting of sodium, calcium, manganese / Yu RJ is a group, NR2R3 / where Rj is hydrogen or a group I, WITH/ 15 R is hydrogen, R4 is hydrogen, alkyl, RP is hydrogen, methyl; 2 & X - oxygen, sulfur, in the amount of 0.1-20 kg / ha. The compounds of formula 1 are processed into various preparative forms: wettable powders, water-soluble powders, suspensions, emulsifiable, concentrates, dusts, solutions, granules, tablets. They are prepared by conventional methods - common in the manufacture of pesticide preparative forms. Predpagay (compounds can be obtained by various methods, for example, by nitro-oxidation of cyanacetic acid with sodium nitrite and acetic acid; from the corresponding hydroxyamyl porous and silk cyanide or c & 1 of its own mineral. Example 1. The active substance is dispersed in water in an amount sufficient to obtain a coaceum of the active compound equal to 400. A portion of the resulting dispersion is diluted to a concentration of 80. The dispersion is sprayed on the ground where plants and tomatoes are planted in the growing pot and allowed to dry. Both treated and untreated plants are infected with a suspension of spores of Ptra-cbphfhbrQ ihtestans and kept for a day in a chamber with saturated. ton moisture. After five days of additional va aurge in feittMite, all loose tomatoes perish due to blight. Plants that were treated with a suspension with a concentration of 80 million active compound had occasional limited damage to f, while plants treated with a suspension of 400 million concentration were healthy without any signs of disease. EXAMPLE 2 Tomato seedlings grown in a vegetative vessel in a greenhouse are contaminated by spraying them with a suspension of PhijiopVi-lViora in estan ' t 4 plants incubated for eight hours in a chamber with saturated humidity. Infected tomato plants are removed from the incubator of the cell chamber and sprayed with various active compounds, 1) add to the disease, as well as; by the formation of these compounds, dispersants, with a concentration of the active compound, 400 million, containing 2-cyio-2-hydroxyimoacetamide. Similar dispersions are prepared from fungicides with the trade name: maneb, capt. Atop, metiram / AT . 1 shows the degree of inhibition of late blight in s & from the active active principle of the formula, 9 {R-O-I-C-C-NH : At a concentration of 80. In 2 shows the degree of pressure of late blight, depending 736856 from the active principle active formula C o -o-ss: mnsmie „ . at a concentration of 80 million In tab. 3 shows the degree of suppression of late blight, depending on the active principle of the active formula 9 H-0-N-C-CNH CNHCH at a concentration of 80 million In tab. 4 shows the degree of suppression of late blight depending on the active active principle 0 of the formula CN (about R-0-N-C-C-NHCNHC, jH5 5 at a concentration of 8b million Table 5 shows the degree of suppression of late blight, depending on the active principle of the formula Hq-N-C-CNHCNHC H and 9 K-O-N C-CNHCNHCjHq -i at a concentration of 80 million 5c table. 6 shows the degree of suppression of late blight, depending on the active principle, formula 9 L CH ON-C-NHCN at a concentration of 80 million 45 For the active acting formula CN S I-C-C-NH ,, t.pl., 163-165 C, 70%; for benomyl, 0% damage. In tab. 7 shows the degree of suppression of the fungal infection: pain in dependence, on the active action at the concentration g 400 million Example 3. Healthy, non-infected plants: tomato spray bi-suspensions and mixtures prepared for testing in a similar manner. Example 2. Treated plants were kept in a greenhouse for five days, then infected with a spore suspension of Pll iopVrtliova infestatis. After the plants grow, they are treated with foliage. . . After incubation, untreated plants die because of late blight. Fungicide trading measures ensure good foliar destruction,; however, new foliage is unprotected and severely affected. The results of the experiments are given in table.3. In tab. 8 shows the degree of suppression of a fungal disease, depending on the active principle at a concentration of 400 ppm. Example 4. Potato field infected with late blight ,. uniformly treated with the composition containing 4-N-carbamoyl-2-cnano-2-methoxyiminoacetamide. The old foliage of each plant has one or two spores of PVi topbtViora infestans. At this stage, the damage to the plants is insignificant, but there is a danger of spreading the Disease. There were deeds of five rows wide and 20 meters long. Plots randomly process the entire field, leaving the raw areas as buffers between the treated plots. In cases after treatment, artificial irrigation conditions are usually created that lead to the spread of the disease. After 7 days, the extent of damage to the plants is determined. The results are shown in table E.,. In tab. 9 shows the dependence of the degree of suppression of the disease depending on the concentration and the species. Example 51 Suspension with a concentration of 400 million active acting containing 2-cyano-2-dodecyl-aminoacetamide is dispersed in water. Part of it is diluted to a concentration of 80 ppm. Dispersions mist the areas where the planted blond plants are dredged and allow them to dry. Both treated and untreated plants are infected with a suspension of Ventuvia inaecj.uotis spores and 6 are kept in a chamber with saturated humidity for one day. The degree of inoculation is assessed after 10 days. The results of the experiment are given in table. ten. Example b. Tomato plants planted in a vegetative vessel are contaminated by spraying them with a spore suspension of phytop Vititora in estar3. The plant is placed in a chamber with saturated Humidity at 20 ° C for eight hours. : 3 infected tomato plants, removed; cabins from the incubation chamber, spray them with the test compound. 0 Plants are returned to the chamber with a saturated effect for 24 hours. After an additional p) day-long incubation in the greenhouse, the percentage of healthy foliage in the treated plants is determined. In tab. 11 shows the degree of inhibition of the disease. Depending on the structure of the active principle of the formula 0 T C-C-CN n O at a concentration of 80 million Thus, the compounds proposed have a high fungicidal action. Table 1 Continued table. one 47-49 163-165 86-87 - (CH); NB - (CH) S, N .. C H --fl 2L CH (CH), / I CH (CHj) CCH (CHj) CN O (skid CH (CH.j) (H {CH) CN OK 140.5-142 . CH, jCH (CH, j) 90.5-92 "For the Ca and Mp salts of the compounds of formula 1, the absorption bands of the IR spectra are shown in microns. 100 60 70 90,100,100 70 80 90 70 .80 70 70 70 20 Table Continued table. 2 Table 3 eleven 736856 Continued table. four Table 5, Table 6 13 .Compound Raw control 2-Cyano-2-oxyiminoacetamide Maneb. Captafsl Metiram Raw control 4-M-Car bamoyl-2-cyano-2-methoxy-amino acetymide Maneb Captafol Metiram Chlorotalonil Raw control 2-Cyano-2-dodecyl iminoacetamide .Maneb Unprocessed 14 Table 1 Degree of suppression f% Table 8 95 ten 15 five T a b l and c a 9 95 90 20 15 10 25 ABOUT -Tables 10 95 100 100 100 Table 11
权利要求:
Claims (1) [1] Claim A method for controlling fungal diseases of plants by treating them or their biotope with an active substance, characterized in that, in order to increase the efficiency of the method, the treatment is carried out with an active substance of the general formula С1Ч x ron = ccr 4 where R is hydrogen, alkyl СС -С13 .., acyl containing 2-4 carbon atoms, ethylacetyl, ethyloxy, alkoxycarbonylmethyl С ^ -Су., Methylcyano, propylcyano, hexylcyano., Alkylene phenyl C 4 -Cj , a metal selected from the group consisting of sodium, calcium, manganese; - - the group NR ^ Rj, where Ro · - hydrogen or the group CN'f * 4 ", * 5 • R ;, - hydrogen ,, TSNIIIPI Order 2455/49 Cd is hydrogen, alkyl-C + , Rg. -. hydrogen, methyl; X ° - oxygen, sulfur. . in the amount of 0.1-20 kg / ha. 40 Priority on grounds; 03/15/72 at. R is hydrogen, ί-13 alkyl, acyl., Containing 2-4 - carbon atoms, alkoxycarbonylmethyl C ^ -C £, a metal selected from the group 45 consisting of sodium, calcium, manganese, R ^ - NR ^ R 3 , where Rj is hydrogen or the group _CN VR5 , Rj is hydrogen, R 4 is hydrogen, Ry is hydrogen. 50 07.02., 7 3 at R - ethylacetyl, ethyloxy ·, methylcyano, propylcyano, hexylcyano, alkylene phenyl C ^ -Cj, Rj - alkyl C 4 -Cd, Ry - methyl ..
类似技术:
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同族专利:
公开号 | 公开日 HU167737B|1975-12-25| PH16838A|1984-03-15| FR2187224B1|1979-02-09| IL41581A|1976-09-30| AU5325873A|1974-09-19| AR208496A1|1977-02-15| GB1425622A|1976-02-18| DE2312956C2|1987-10-01| EG10809A|1976-06-30| FR2187224A1|1974-01-18| AU474556B2|1976-07-29| GB1425621A|1976-02-18| JPS5828243B2|1983-06-15| IT979609B|1974-09-30| CH570106A5|1975-12-15| ZA731111B|1974-03-27| CA1040530A|1978-10-17| DD105112A5|1974-04-12| CS190387B2|1979-05-31| JPS49427A|1974-01-05| DE2312956A1|1973-09-20| IL41581D0|1973-04-30|
引用文献:
公开号 | 申请日 | 公开日 | 申请人 | 专利标题 FR1542325A|1966-11-10|1968-10-11|Ciba Geigy|New pesticide agents| CH484604A|1966-11-10|1970-01-31|Ciba Geigy|Pesticides| US3694482A|1970-04-15|1972-09-26|Exxon Research Engineering Co|Malononitrile oxime derivatives|IE38344B1|1972-10-13|1978-02-15|Ciba Geigy Ag|Cyano-hydroxyimino-acetamide derivatives as plant growth regulants and fungicides| ZA757990B|1975-01-30|1976-12-29|Du Pont|Stabilized formulations of 2-alkoxyiminon-carbamoyl-2-cyanoacetamides| DK333276A|1975-09-11|1977-03-12|Du Pont|FUNGICIDE, SUBSTITUTED 2-CYANOACET AMID DERIVATIVES| DE2552867A1|1975-11-25|1977-06-02|Du Pont|Fungicide compsn. - contg. -cyano--ethyl-carbamoyl--methoxy-imino-acetamide| JPS5266631A|1975-12-02|1977-06-02|Du Pont|Combined germicide| US4178383A|1976-05-28|1979-12-11|Bayer Aktiengesellschaft|Fungicidally active oxime-ethers of isonitrosocyanoacetamides| US4188401A|1977-06-04|1980-02-12|Bayer Aktiengesellschaft|Combating fungi with 1--3--ureas| AT365410B|1978-08-31|1982-01-11|Ciba Geigy Ag|AGENT FOR THE PROTECTION OF CULTIVATED PLANTS FROM AGGRESSIVE VEGETABLES| DE2837863A1|1978-09-04|1980-03-13|Ciba Geigy Ag|OXIME DERIVATIVES FOR THE PROTECTION OF PLANT CULTURES| DE3041998A1|1980-11-07|1982-06-09|Bayer Ag, 5090 Leverkusen|PYRAZOLE-SUBSTITUTED OXIMINO-CYAN-ACETAMIDE DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS FUNGICIDES| JPS6226461Y2|1981-09-24|1987-07-07| CH654979A5|1982-01-26|1986-03-27|Sandoz Ag|FUNGICIDES AND THEIR USE.| DE3206235A1|1982-02-20|1983-09-01|Bayer Ag, 5090 Leverkusen|SUBSTITUTED OXIMINOACETANILIDES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS A PEST CONTROL| DE3222961A1|1982-06-19|1983-12-22|Bayer Ag, 5090 Leverkusen|AZOL SUBSTITUTED OXIMINO CYAN ACETAMIDE DERIVATIVES| JPS6139182U|1984-08-07|1986-03-12| JPS61103485U|1984-12-07|1986-07-01| DE3602243A1|1985-06-13|1986-12-18|Bayer Ag, 5090 Leverkusen|E-ISOMERS OF N-AMINO ACID DERIVATIVES AND PEPTIDES| DE3625497A1|1986-07-28|1988-02-11|Bayer Ag|E / Z ISOMERIC MIXTURES AND PURE Z ISOMERS OF N-AMINO ACID DERIVATIVES AND PEPTIDES| DE3630732A1|1986-09-10|1988-03-17|Bayer Ag|2-CYANO-2-ALKOXIMINO ACETAMIDE| US5231109A|1986-09-10|1993-07-27|Bayer Aktiengesellschaft|2-cyano-2-alkoximino-acetamides| DE3702283A1|1987-01-27|1988-08-04|Bayer Ag|METHOD FOR PRODUCING 2-CYANO-2-OXIMINO ACETAMIDE DERIVATIVES| DE10347090A1|2003-10-10|2005-05-04|Bayer Cropscience Ag|Synergistic fungicidal drug combinations| DE10349501A1|2003-10-23|2005-05-25|Bayer Cropscience Ag|Synergistic fungicidal drug combinations| DE102005026482A1|2005-06-09|2006-12-14|Bayer Cropscience Ag|Active substance combination, useful e.g. for combating unwanted phytopathogenic fungus, comprises herbicides e.g. glyphosate and active substances e.g. strobilurin, triazoles, valinamide and carboxamide| PL1893024T3|2005-06-09|2011-04-29|Bayer Cropscience Ag|Active substance combinations| DE102006023263A1|2006-05-18|2007-11-22|Bayer Cropscience Ag|Synergistic drug combinations| DE102007045920B4|2007-09-26|2018-07-05|Bayer Intellectual Property Gmbh|Synergistic drug combinations| UA104887C2|2009-03-25|2014-03-25|Баєр Кропсаєнс Аг|Synergic combinations of active ingredients| WO2011006603A2|2009-07-16|2011-01-20|Bayer Cropscience Ag|Synergistic active substance combinations containing phenyl triazoles| EP2910126A1|2015-05-05|2015-08-26|Bayer CropScience AG|Active compound combinations having insecticidal properties|
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申请号 | 申请日 | 专利标题 US23499772A| true| 1972-03-15|1972-03-15| US33045773A| true| 1973-02-07|1973-02-07| 相关专利
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