JPH0330564B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention is based on the general formula [] [In the formula, R represents a lower alkyl group, a cycloalkyl group, or a halo-lower alkyl group. ] N-phenyltetrahydrophthalimide derivative represented by
Butylidene]-4-methoxycarbonyl-5,5
-dimethylcyclohexane-1,3-dione (or its salt, hereinafter referred to as alloxydim) or 2-[1-(ethoxyimino)butyl]-5-(2-
The present invention relates to a herbicidal composition containing ethylthiopropyl)-3-hydroxy-2-cyclohexen-1-one (hereinafter referred to as setoxydim) as an active ingredient. Currently, many herbicides are used as herbicides for upland fields, but because there are many types of weeds to control and they occur over a long period of time, they are more effective at killing weeds and have a wider herbicidal spectrum. There is a need for safe herbicides for crops. As a result of various studies on these points, the present inventors have discovered a compound useful as a selective herbicide in soybean fields (Japanese Patent Application No. 56-212396, 57
-13845, 57-17858) and alloxydim (or its salt) or setoxydim (Tetsuo Takematsu, Herbicide Research Directory, P.700-704, which is already known as a selective herbicide for crops such as soybean). Hakuyusha,
The herbicidal composition of the present invention containing as an active ingredient a variety of weeds, especially a wide range of weeds in soybean fields, and its herbicidal effect is higher than that when used alone. The present invention was completed based on the discovery that the drug increases synergistically and can be applied at a low dosage. Weeds that can be used as a control for the herbicidal composition of the present invention include monocots such as foxtail grass, blackberry grass, blackberry grass, Japanese grasshopper, Seiban sorghum, and grasshopper; There are morning glories such as the morning glory, and dicotyledonous plants such as the American hornwort, the American kingfisher, the goldenrod, and the wild sunflower. The herbicidal composition of the present invention can simultaneously weed weeds that are particularly difficult to weed, such as morning glories such as Seiban sorghum, grasshopper, and morning glory, Japanese sorghum, and Japanese fir tree. The mixing ratio of the compound [] which is the active ingredient of the herbicidal composition of the present invention and alloxydim (or its salt) or setoxydim can be varied over a relatively wide range, but is usually based on 1 part by weight of the compound []. Alloxydim (or a salt thereof) or setoxydim is 0.1 to 50 parts by weight, preferably 0.5 to 50 parts by weight.
It is 20 parts by weight. Table 1 shows some of the compounds [ ] that are the active ingredients of the herbicidal composition of the present invention and alloxydim (Na salt).
and setoxydim. The compound numbers shown in Table 1 are commonly used in the following formulation examples and test examples.

【table】

[Table] When the herbicidal composition of the present invention is used as a herbicide, it is usually formulated into emulsions, wettable powders, suspensions, and granules using solid carriers, liquid carriers, surfactants, and other formulation auxiliaries. etc. These preparations contain active ingredients in a weight ratio of 0.5 to
90%, preferably 2-80%. Solid carriers include kaolin clay, attabulgite clay, bentonite, acid clay, birofluorite, talc, diatomaceous earth, calcite, walnut powder,
There are fine powders or granules such as urea, ammonium sulfate, and synthetic hydrous silicon oxide, and liquid carriers include aromatic hydrocarbons such as xylene and methylnaphthalene.
Examples include alcohols such as isoparopanol, ethylene glycol, and cellosolve, ketones such as acetone, cyclohexanone, and isophorone, vegetable oils such as soybean oil and cottonseed oil, dimethyl sulfoxide, acetonitrile, and water. Surfactants used for emulsification, dispersion, wetting, etc. include negative salts such as alkyl sulfate salts, alkyl (aryl) sulfonate salts, dialkyl sulfosuccinate salts, and polyoxyethylene alkylaryl ether phosphate salts. Examples include ionic surfactants, nonionic surfactants such as polyoxyethylene alkyl ether, polyoxyethylene alkylaryl ether, polyoxyethylene polyoxypropylene block copolymer, sorbitan fatty acid ester, and polyoxyethylene sorbitan fatty acid ester. Formulation auxiliaries include lignin sulfonate, alginate, polyvinyl alcohol, gum arabic, CMC (carboxymethyl cellulose), and PAP (isopropyl acid phosphate).
etc. Examples of formulations are shown below. Note that parts indicate parts by weight. Formulation Example 1 20 parts of compound (2), 30 parts of compound (i) (acid), 3 parts of calcium lignosulfonate, 2 parts of sodium lauryl sulfate, and 45 parts of synthetic hydrous silicon oxide are thoroughly ground and mixed to obtain a wettable powder. . Formulation Example 2 5 parts of compound (1), 15 parts of compound (ii), 14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzenesulfonate, 30 parts of xylene and 30 parts of isophorone are thoroughly mixed to obtain an emulsion. . Formulation Example 3 1 part of Compound (3), 1 part of Compound (ii), 1 part of synthetic hydrous silicon oxide, 2 parts of calcium ligninsulfonate, 30 parts of bentonite and 65 parts of kaolin clay are thoroughly ground and mixed, and water is added. After kneading, the mixture is granulated and dried to obtain granules. Formulation Example 4 5 parts of compound (4), 20 parts of compound (ii), 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of CMC and 69 parts of water were mixed and wet-pulverized until the particle size became 5 microns or less. Obtain a clouding agent. Formulation Example 5 5 parts of compound (4), 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of CMC and 69 parts of water were mixed and wet-pulverized until the particle size became 5 microns or less, and then compound (i) (Na salt) was mixed. ) to obtain a suspension. These preparations can be used as they are or diluted with water, etc. for foliage or soil treatment. In addition, by mixing it with other herbicides, it can be expected that the herbicidal effect will be improved. Furthermore, it can be used in combination with insecticides, acaricides, nematicides, fungicides, plant growth regulators, fertilizers, soil conditioners, and the like. The application amount of the herbicidal composition of the present invention varies depending on weather conditions, soil conditions, formulation form of the composition, mixing ratio of active ingredients, target weeds and crops, etc., but usually the total amount of active ingredients per are is 1 to 20 g. be. Emulsions, wettable powders, suspensions, etc. should be diluted with 1 to 10 liters of water per area (if necessary, a spreading agent such as a spreading agent may be added), and granules, etc. should be applied. Apply as is without any dilution. In addition to the above-mentioned surfactants, the spreading agent includes polyoxyethylene resin acid (ester), lignin sulfonate, abietate, dinaphthylmethane disulfonate, paraffin, and the like. Next, a test example will be given to specifically demonstrate the herbicidal effect of the herbicidal composition of the present invention. The herbicidal efficacy is expressed as a growth inhibition rate (%) calculated from the following formula by weighing the fresh weight of the above-ground parts of the test plants that remained dead at the time of the survey. Growth inhibition rate (%) = (1 - fresh weight of above-ground parts of test plants in treated area / fresh weight of above-ground parts of test plants in non-treated area) × 100 Test example 1 Cylindrical with a diameter of 10 cm and a depth of 10 cm A shaped plastic pot was filled with field soil, seeded with Seiban sorghum or barnyard grass, covered with soil, and grown outdoors for 20 days. A predetermined amount of the test compound made into a wettable powder according to Formulation Example 1 was diluted with water containing a spreading agent, and sprayed on foliage from above a plastic pot using a small sprayer at a rate of 10 liters per are. The test plants were at the 3-4 leaf stage at the time of spraying. After spraying, the plants were grown outdoors for 20 days and their herbicidal efficacy was investigated. The results are shown in Tables 2 and 3.

【table】

【table】

【table】

[Table] Test Example 2 A vat with an area of 33 x 23 cm ² and a depth of 11 cm was filled with field soil, and wild foxtail, goldenberry, Seiban sorghum, mulberry morning glory, Japanese velvet, Japanese fir, and soybean were sown and grown for 18 days. Thereafter, a predetermined amount of the test compound made into a hydrating powder according to Formulation Example 1 was diluted with water containing a spreading agent, and sprayed from above the plant over the entire stem and leaf area using a small sprayer at a rate of 5 liters per are. was evenly distributed. At this time, the growth of each plant varied depending on the grass species, but was at the 1- to 4-leaf stage.
Herbicidal efficacy was investigated 20 days after spraying. The results are shown in Table 4. Note that this test was conducted outdoors throughout the entire period.

【table】

Claims (1)

[Claims] 1. General formula [In the formula, R represents a lower alkyl group, a cycloalkyl group, or a halo-lower alkyl group. ] N-phenyltetrahydrophthalimide derivative represented by and 2-[1-(N-allyloxyamino)
Butylidene]-4-methoxycarbonyl-5,5
-dimethylcyclohexane-1,3-dione (or salt thereof) or 2-[1-[ethoxyimino]
butyl]-5-(2-ethylthiopropyl)-3-
A herbicidal composition comprising hydroxy-2-cyclohexen-1-one as an active ingredient.