SU820646A3 - Herbicidic composition - Google Patents

Abstract

1501811 Pesticidal application of pyridyltriazinones SUMITOMO CHEMICAL CO Ltd 20 Jan 1976 [21 Jan 1975 14 Feb 1975] 02231/76 Heading A5E [Also in Divisions A2 and C2] A method of controlling, innibiting or preventing the growth of plant-life or fungus comprises administering to the plant-life or fungus, or treating or impregnating a substrate on which the growth of plant-life or fungus is to be prevented with, a compound of the formula: wherein R is a hydrogen atom, an alkyl group having from 1 to 5 carbon atoms, a phenyl group or an alkoxycarbonylmethyl group whereof the alkoxy moiety contains from 1 to 3 carbon atoms. Optionally fungicides, insecticides, nematocides, acaricides, herbicides and fertilizers also may be present. Suitable compositions also are claimed.

Description

(54) HERBICIDE COMPOSITION

This invention relates to a chemical plant protection agent, specifically a herbicidal composition based on 1,2,4-triazin-5-one derivatives. A herbicide is known, whose 1,2,4-triazin-5-one derivatives are the most effective substance. The herbicide based on 6-phenyl-1,2, 4-triazin-5-one derivatives is the closest to the invention. However, the indicated herbicides rb insufficient activity at low concentrations. The aim of the invention is to obtain new herbicidal agents having high herbicidal activity. This is achieved by the use of 1,2,4-triazin-5-one derivatives of the compound oOiuefi Formula G OFP tffa A - -IN-CH and / "- K With R - R - hydrogen, methyl, ethyl, tert-butyl, methoxycarbonylmethyl , ethoxycarbonylmethyl, phenyl in an amount of 0.1-95 wt.%. The compounds of general formula 1 can be obtained by various methods, as well as compounds where A is the group -NH-CH (R) - are prepared by reacting the picolinamidrazone of formula II. N-Vng with haloacetic acid or its forglula I I 1 B X-dH-COOR ester in which X is a halogen; R is hydrogen or alkyl C — C — R has the indicated meanings. The reaction is carried out in an inert solvent (benzene, chlorobenzene, toluene, xylene, ligoroin, hexane, isopropyl ether, tetrahydrofuran, dioxane, chloroform, methanol, ethanol, isopropanol, water), preferably in the presence of an acid-binding agent (sodium hydroxide, hydroxide sodium methylate, sodium ethoxide, pi: ridine, triethylamine, dimethylaniline, diethylaniline) over a wide temperature range. By oxidizing the obtained compounds, compounds can be obtained, and of which A group NC (R) is oxidized in an inert solvent, for example, in methanol, ethanol from propyl ether, tetrahydrofuran, dioxime, acetone, chloroform by irradiation with light or by using an oxidant, for example chromic acid , perchromic acid, Kali manganate, manganese dioxide, aqueous hydrogen peroxide, perbenzoic acid. In addition, compounds of general formula I, where ANC {R) is obtained by the mutual action of a compound of formula Ib with a keto acid or its ester of formula IV H-0-COOBi, where R and R have the indicated values. The reaction is carried out in an inert solvent, for example water , methanol, ethanol, isopropyl ether, tetrahydrofuran, dioxane, acetone, chloroform, in a wide range of temperatures. In addition, compounds of general formula I, where R is alkoxycarbonylmethyl, and A is a group (R) -, are obtained by reacting a compound of formula JI with an acetylenedicarboxylic ester of the formula V BOOC-1 t-teOT j, where R is C; Cj is alkyl. The reaction is carried out in an inert solvent, for example, methanol, ethanol, isopropyl ether, tetrahydrofuran, dioxane, acetone, chloroform, over a wide range of temperatures. Compounds of the general formula t shown in Table 2 are obtained in a similar manner. Forms of application are common: dusts, granules, fine granules, wettable powders and emulsified flax concentrates. Such preparations can be prepared in combination with solid and liquid carriers. Talc, bentonite, clay, koalin, diatomaceous earth, vermiculite, limestone, etc. can be used as solid carriers, and benzene, alcohols, acetone, xylene, methylnaphthalene, dioxane, cyclohexanone, etc., can be used as liquid carriers. d. Compounds of general formula 1 can be used together with surfactants or in combination with agricultural chemicals, such as fungicides, insecticide and fertilizers, as well as with other herbicides. Example 1. Application before germination. Large blood rosary is used as representatives of grass weeds of red-root axiris and common white as representatives of broadleaf weeds, as well as wheat and radish as representatives of cultivated plants. Seeds of herbs and cultivated plants are sown in pots and covered with soil. The emulsifiable concentrate containing the test compound is diluted with water and sprayed onto the soil using a hand sprayer. Each weed each crop is grown in a greenhouse, the herbicidal activity of the test compound is calculated 20 days after application. Herbicidal activity is assessed on a scale lying in the range from 0 to 5. 0-0, 1-20, 2-40, 3-60, 4-80, 5-100% inhibition. The results are shown in Table. 2. PRI mme R 2. Use when flooded with water. Wagner's Csoiou, having a diameter of 14 cm, is filled with 1.5 kg of soil from a rice field. Rice saplings in the stage of 3 leaves are transferred to the bowl and then the seeds of chicken millet are sown. The test compound is applied to the soil under its flooding conditions with water. Twenty-five days after application, the herbicidal activity and phytotoxicity of the test compound are calculated on transferred and sown plants, as well as on arbitrarily sprouted broadleaf weeds, such as monochorus, false femoral. A wetting powder containing the test compound 15 ml per bowl is applied, spread by pipette. Herbicidal activity is assessed as in Example 1. The phytotoxicity is evaluated as follows. Calculate the ratio (%) of each of the three factors: the height of the grass, the number of shoots, the total dry weight in the treated bowl compared to the value in the untreated bowl. For evaluation take mi. The lowest of 3 values, Phytotoxicity is assessed on a scale of 0: 100; 1-80-, 2-60; 3-40v 4-20; 5-0%. The results are shown in Table. 3. TC1, the proposed compounds have a high herbicidal activity at low concentrations.

Nn n

- x

-

N iTlf "About

 N N N

"ABOUT

/

-O / h // - sngsoosnd

N

Och1- °

N Nil

Table 1

138 - 139

151 - 151.5

162 - 164

 lSgNz

n

167 - 168

217 - 219 (with decomposition)

299 - 300

114 - -115

124 - 126

136 - 137

CHzCOOCzHj

ten

177 - 178

table 2

Claims (2)

The formula of the invention of activity, it contains as Herbicidal x-positioning, containing 1,2,4-triazin-5-one derivative, connecting 1,2,4-triazing-5-1 derivatives. It is 60 degrees of the general formula, as an active substance, anH, v also an additive selected from the group; H- solvent, emulsifier-, solid carrier, characterized in that. what about increasing herbicide 65 That blitz 3 is where A is NH — CH— or —N — C—, where R is hydrogen, ethyl, tert-butyl, mé: toxicarbonylmethyl, ethoxycarbonylmethyl, phenyl in an amount of 0.1-95 wt. Priority signs: R 21.01.75 with A-BN-hydrogen, methyl, ethyl, tert-butyl or; phenyl. 14.02.75 with A- -11 0 R - hydrogen, methyl, ethyl, tert-butyl, methoxycarbonylmethyl, ethoxycarbonylmethyl or phenyl. Sources of information taken into account in the examination 1. Japanese Patent No. 44-315, class, 30F, published. 1969. 2. Japan patent 45-201066, cl. 30F, pub. 1970 (prototype).