JPS635363B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention is based on the formula [] N-(α,α-dimethylbenzyl)-α represented by
- A mixture of bromotarsiabutylacetamide (compound []) and one or more compounds selected from the group of compounds represented by the following formulas [], [], and [] (hereinafter referred to as compound group A). It is a herbicide characterized by: formula〔〕 O-ethyl-O-(3-methyl-6-
nitrophenyl)-N-secondary butyl phosphorothioamidate (compound []) Formula [] O,O-diphenyl S-(2-methylpiperidin-1-ylcarbonylmethyl)phosphorodithioate (compound []) represented by formula [] N-(O,O-dipropyl-dithiophosphorylacetyl)-2-methylpiperidine (compound [ ]) Herbicides are, in principle, used to control many types of weeds that occur in fields, paddy fields, orchards, and other areas targeted for weed control. It will not be fully effective unless all weeds are killed. For example, if some weeds survive, they can grow larger and more harmful, reducing the effectiveness of herbicides by half. Due to these characteristics of weed control, herbicides that are particularly effective against a wide variety of weeds and have a wide weed spectrum are desired. If you just want to increase the herbicide effect, you may be able to achieve your goal by increasing the amount of herbicide applied, but this will also increase the chemical damage to the crop, which goes against the original goal of weed control, which is to secure yield. Become. On the other hand, since environmental pollution caused by certain types of pesticides has recently become a problem, there is a desire to develop herbicides that are effective even when applied in small amounts, even if they are pesticides with low persistence. Under the above circumstances, the present inventors are conducting research with the aim of developing an excellent herbicide that meets the above conditions. It has been shown that a mixture with one or more of the compounds selected from compound group A shown in [ ], [ ], and [ ] exhibits a remarkable synergistic effect that cannot be seen with conventional mixed use of herbicides. Based on this new finding, we have completed the herbicide of the present invention, which has a wide spectrum of weeds at a low application rate. To explain the present invention in more detail, the compound [], which is one of the components of the herbicide, was previously invented by the present inventors (Japanese Patent Application No. 115588/1988),
It is highly effective against firefly, etc., and is also highly safe against rice. It is also active against wild grasses, annual broad-leaved weeds, and perennial weeds that have become a problem in recent years, such as black croaker, Japanese cypress, and urticaria, when treated in the early stages of growth, but the effect becomes weaker as growth progresses. In order to compensate for the drawbacks of this compound, we investigated mixtures with various herbicides. The compound represented by the formula [] is
16854, the compound represented by the formula [] is known in JP-A-52-28941, and the compound represented by the formula [] is known in British Patent No. 1255946, respectively, and the compounds represented by the formula [], [] and [] The organic phosphorus compounds shown in ] have a common property that they are highly effective against novied insects, but are somewhat less effective against firefly, black grub, black snail, orchid, etc. The mixture of compound [] and compound group A exhibits a synergistic effect that could not be expected from the mixture of each single agent, and has the extremely useful property of being able to control many weeds with a low dose. The present invention was completed based on the new findings. Furthermore, in order to further strengthen the herbicidal action of the mixed herbicide of the present invention, 2-methylthio-4,6-bis(ethylamino)-S-triazine, α-(β-naphthoxy)propionanilide or 3-isopropyl-1H -2,1,3-benzothiadiazine-(4)-3H-one-2,2-dioxide and the like are also effective methods. The synergistic effect related to the present invention is observed in a wide range of mixing ratios, and preferably compound group A is mixed at a ratio of 0.2 to 5 parts by weight to 1 part by weight of the compound [] to produce a useful herbicide. can be created. The herbicide of the present invention, which has been completed in this way, is effective even when treated before and after the germination of weeds, and can be applied not only to paddy rice but also to soil treatment and leaf spraying, where it can be highly effective. about,
It is useful for various shellfish, legumes, cotton, vegetables, orchards, lawns, pastures, tea gardens, mulberry gardens, forest land, non-agricultural land, etc. The mixture of the present invention may be sprayed as a raw material itself, or may be mixed with a carrier and other auxiliary agents as necessary to form a formulation commonly used as a herbicide, such as powder, coarse powder, fine granule, etc. It is used after being prepared into granules, wettable powders, emulsions, flowable preparations, aqueous solutions, aqueous solutions, oil suspensions, etc. Suitable solid carriers for use in preparing the herbicide of the present invention include clays represented by the kaolinite group, montmorillonite group, or attapulgite group, talc, mica, pyrophyllite, pumice, vermiculite, and gypsum. , calcium carbonate, dolomite, diatomaceous earth, magnesium lime, apatite, zeolite, anhydrous silicic acid, synthetic calcium silicate and other inorganic substances, soybean flour, tobacco flour, walnut flour, wheat flour, wood flour, starch, crystalline cellulose. vegetable organic substances such as coumaron resin, petroleum resin, alkyd resin, polyvinyl chloride, polyalkylene glycol, ketone resin, synthetic or natural polymer compounds such as ester gum, cobal gum, dammar gum, wax such as carnauba wax, beeswax, etc. and urea. Suitable liquid carriers include paraffinic or naphthenic hydrocarbons such as kerosene, mineral oil, spindle oil, white oil, aromatic hydrocarbons such as benzene, toluene, xylene, ethylbenzene, cumene, methylnaphthalene, carbon tetrachloride, chloroform, etc. , chlorinated hydrocarbons such as trichloroethylene, monochlorobenzene, o-chlorotoluene, ethers such as dioxane and tetrahydrofuran, ketones such as acetone, methyl ethyl ketone, diisobutyl ketone, cyclohexanone, acetophenone, isophorone, ethyl acetate, amyl acetate, Esters such as ethylene glycol acetate, diethylene glycol acetate, dibutyl maleate, diethyl succinate, alcohols such as methanol, n-hexanol, ethylene glycol, diethylene glycol, cyclohexanol, benzyl alcohol, ethylene glycol ethyl ether, ethylene glycol phenyl ether , ether alcohols such as diethylene glycol ethyl ether and diethylene glycol butyl ether, dimethylformamide,
Examples include polar solvents such as dimethyl sulfoxide, water, and the like. Emulsification, dispersion, wetting, spreading, binding, disintegration control,
Surfactants used for the purpose of stabilizing active ingredients, improving fluidity, and preventing rust can be nonionic, anionic, cationic, or amphoteric, but usually used are nonionic and/or anionic. Suitable nonionic surfactants include, for example, those obtained by polymerizing and adding ethylene oxide to higher alcohols such as lauryl alcohol, stearyl alcohol, and oleyl alcohol, and those obtained by polymerizing and adding ethylene oxide to alkyl phenols such as isooctylphenol and nonylphenol. products obtained by polymerizing and adding ethylene oxide to alkylnaphthols such as butylnaphthol and octylnaphthol, products obtained by polymerizing and adding ethylene oxide to higher fatty acids such as palmitic acid, stearic acid, and oleic acid, stearyl phosphoric acid, dilauryl phosphoric acid, etc. mono- or dialkyl phosphoric acid with ethylene oxide polymerized and added, amines such as dodecylamine and stearic acid amide with ethylene oxide polymerized and added, higher fatty acid esters of polyhydric alcohols such as sorbitan, and ethylene oxide polymerized and added to them. Examples include those obtained by polymerizing and adding ethylene oxide and propylene oxide. Suitable anionic surfactants include, for example, sodium lauryl sulfate, alkyl sulfate salts such as oleyl alcohol sulfate amine salts, alkyl sulfonates such as sodium sulfosuccinate dioctyl ester, and sodium 2-ethylhexene sulfonate. , aryl sulfonates such as sodium isopropylnaphthalene sulfonate, sodium methylene bisnaphthalene sulfonate, sodium lignin sulfonate, and sodium dodecylbenzenesulfonate. Furthermore, the herbicide of the present invention includes casein, gelatin, albumin, glue, sodium alginate, carboxymethyl cellulose, methyl cellulose,
High molecular compounds such as hydroxyethyl cellulose and polyvinyl alcohol and other auxiliary agents can also be used in combination. The above-mentioned carriers and various auxiliary agents are used in the dosage form of the preparation,
They are used individually or in combination as appropriate depending on the purpose, taking into consideration the application situation. Powders, for example, usually contain 1 to 25 parts by weight of the active ingredient compound, with the remainder being a solid carrier. Wettable powders usually contain, for example, 25 to 90 parts by weight of the active ingredient compound, with the remainder being a solid carrier, a dispersing wetting agent, and optionally a protective colloid agent, a thixotropic agent, an antifoaming agent, and the like. Granules, for example, usually contain 1 to 35 parts by weight of the active ingredient compound, with the remainder being mostly solid carrier. The active ingredient compound is uniformly mixed with the solid carrier, or is uniformly fixed or adsorbed on the surface of the solid carrier, and the particle size is about 0.2 to
It is about 1.5mm. An emulsion, for example, usually contains 5 to 30 parts by weight of the active ingredient compound, including about 5 to 20 parts by weight of an emulsifier, with the remainder being a liquid carrier;
Rust inhibitors are added if necessary. Examples of formulations of this herbicide are shown below. Formulation example 1 Compound [] 20 parts by weight, compound [] 20 parts by weight, dodecylbenzenesulfonate 2.5 parts by weight,
2.5 parts by weight of lignin sulfonate and 55 parts by weight of diatomaceous earth
The weight parts are thoroughly ground and mixed to obtain a wettable powder. Formulation Example 2 15 parts by weight of the compound [], 10 parts by weight of the compound [], 15 parts by weight of the emulsifier Sorbol SM100 (registered trademark of Toho Chemical) and 60 parts by weight of xylene are thoroughly mixed to obtain an emulsion. Formulation Example 3 3 parts by weight of compound [], 5 parts by weight of compound [], 3 parts by weight of white carbon, 5 parts by weight of lignin sulfonate, and 84 parts by weight of clay were thoroughly ground and mixed, water was added, and the mixture was thoroughly kneaded. The granules are dried to obtain granules. Formulation Example 4 1 part by weight of compound [], 3 parts by weight of compound [], 1 part by weight of isopropyl phosphate, 65 parts by weight of clay and 30 parts by weight of talc are thoroughly ground and mixed to obtain a powder. Formulation Example 5 40 parts by weight of bentonite, 5 parts by weight of lignin sulfonate and 55 parts by weight of clay are pulverized and mixed, water is added, kneaded and granulated and dried to produce granules containing no active ingredient. Granules are obtained by impregnating 95 parts by weight of the granules with 1 part by weight of the compound [] and 4 parts by weight of the compound []. Next, the present invention will be explained in more detail with reference to Examples. Example 1 A 14 cm diameter Wagner pot filled with 1.5 kg of paddy soil each was filled with water to create a paddy field, and the pots were filled with Japanese millet, bulrush, Japanese azalea, and Japanese azalea.
Seeds of broad-leaved weeds such as Kikashigusa were sown, and tubers of Japanese cypress, Japanese cypress, and Japanese cypress were planted. Furthermore, we transplanted rice seedlings at the 3-leaf stage and made 25 pots.
Plants were grown in a iron house at ~30°C, and on the 7th day after sowing, when the barnyard grass was at the 0.7 leaf stage, a predetermined amount of the drug was formulated into a wettable powder, diluted with water, and 15c per pot. .c. processed. The plants were then grown in a Firelon house, and the herbicidal effect was investigated on the 25th day after the chemical treatment. The herbicidal effect was expressed as a number from 0 to 10 as shown below based on the observation of the weed suppression rate, degree of withering, etc. The results are shown in Table 1. Weed suppression rate 0: 0-9% 1:10-19 2:20-29 3:30:39 4:40-49 5:50-59 6:60-69 7:70-79 8:80-89 9: 90-99 10: 100 (Complete death)

[Table] Example 2 Fill a 1/5000a Wagner pot with soil,
After the rice field was established, Japanese millet was sown. twenty five
The plants were grown in a greenhouse at 1.8°C and treated with the dosage form shown in Formulation Example 2 at the prescribed dosage at the 1.8 leaf stage. The herbicidal effect was investigated 30 days after chemical treatment. The fresh weight of the aboveground parts of Japanese millet was measured, and the suppression ratio against the untreated plot was calculated. The results are shown in Table 2. Based on this table, the data showing the synergistic effect is summarized in "Weed Research" No. 14, No. 12~
Cited in the citations on page 18 (1973).
Tammes' method [Tammes, PML: Neth J.
Plant Path., Vol. 70, pp. 73-80 (1964)]. The results are shown in FIG. 1. As is clear from FIG. 1, the 90% iso-effect curve lies inside the additive effect curve, and it can be said that this mixture has a synergistic effect.

[Table] Example 3 Fill a 1/5000a Wagner pot with soil,
After the rice field was established, Japanese millet was sown. twenty five
The plants were grown in a greenhouse at 1.8°C and treated with the dosage form shown in Formulation Example 2 at the prescribed dosage at the 1.8 leaf stage. The herbicidal effect was investigated 30 days after chemical treatment. The fresh weight of the aboveground parts of Japanese millet was measured, and the suppression ratio against the untreated plot was calculated. The results are shown in Table 3. Based on this table, the data showing the synergistic effect is summarized in "Weed Research" No. 14, No. 12~
Cited in the citations on page 18 (1973),
Tammes' method [Tammes, PML: Neth J.
Plant Path., Vol. 70, pp. 73-80 (1964)]. The results are shown in FIG. 2. As is clear from FIG. 2, the 90% iso-effect curve lies inside the additive effect curve, and it can be said that this mixture has a synergistic effect.

【table】 [Brief explanation of the drawing]

Figures 1 and 2 show the effect of this mixed herbicide.
This was shown using Tammes' method. The horizontal axis shows the application amount of compound [], and the vertical axis shows the application amount of compound [].

Claims (1)

[Scope of Claims] 1 N-(α,α-dimethylbenzyl)-α-bromotarsiabutylacetamide and O-ethyl-O-(3-methyl-6-nitrophenyl)-N-
secondary butyl phosphorothioamidate,
One type of compound selected from O,O-diphenyl S-(2-methylpiperidin-1-ylcarbonylmethyl)phosphorodithioate and N-(O,O-dipropyl-dithiophosphorylacetyl)-2-methylpiperidine A herbicide characterized by being a mixture of the above. 2 N-(α,α-dimethylbenzyl)-α-bromothyabutylacetamide and O-ethyl-O-(3-methyl-6-nitrophenyl)-N-
The herbicide according to claim 1, which is obtained by mixing with secondary butyl phosphorothioamidate in a ratio of 1:0.2 to 5 (weight ratio). 3 N-(α,α-dimethylbenzyl)-α-bromota-syabutylacetamide and O,O-diphenyl S-(2-methylpiperidin-1-ylcarbonylmethyl)phosphorodithioate in a ratio of 1:0.2 to 5 (weight ratio). 4 N-(α,α-dimethylbenzyl)-α-bromotarsiabutylacetamide and N-(O,
O-dipropyl-dithiophosphorylacetyl)-
2-methylpiperidine and 1:0.2-5 (weight ratio)
The herbicide according to claim 1, wherein the herbicide is mixed in a proportion of .