JPS6323807A - Herbicidal composition - Google Patents

Abstract

PURPOSE:A herbicidal composition, containing a specific amide compound and a specific sulfonylurea base compound together, having herbicidal effect in a small amount of chemical and low concentration as well as a wide herbicidal spectrum and useful as a selective herbicide for wheat. CONSTITUTION:A herbicidal composition containing (A) a compound expressed by formula I (R1 is formula II or III) and (B) one or more of compounds expressed by formula IV (R2 is Cl or COOCH3; R3 is H or CH3), e.g. 2-chloro-N-( 4-methoxy-6-methyl-1,3,5-triazin-2-ylaminocarbonyl )benzenesulfonamide, methyl 2-[3-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)ureidosulfonyl)benzoate or methyl 2-[3-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-3-methylureido-sulfonyl]b enzoate, preferably at 1:0.001-0.1 weight ratio of the ingredients (A) to (B).

Description

[Detailed Description of the Invention] [Industrial Application Field] The present invention relates to an amide compound represented by the general formula (■): t shown) and a general formula (■): (in which R
3 represents a chlorine atom or -COCH3, and R1 represents a hydrogen atom or a methyl group.

The herbicidal composition of the present invention is useful in the agricultural field, particularly as a selective herbicide for wheat.

[Conventional technology]

2-chloro-N-(4-methoxy-6-methyl-1,3,5-triazin-2-yl-aminocarbonyl)benzene, which has been conventionally used as a herbicide in wheat fields, barley fields, and rye fields. Sulfonamide (- Ship name; Chlorosulfuron (hereinafter referred to as "Compound C"), Methyl 2-(3-(4-methoxy-6-methyl-1,3,
5-triazin-2-yl)ureidosulfonyl]benzoate (-ship name: metsulfuron methyl) (hereinafter referred to as "Compound D"), methyl 2- (3-(4-methoxy-6-methyl-1,3, 5-triazin-2-yl)
-3-methylureidosulfonyl]benzoate (-ship name: D P X -15300) (hereinafter referred to as "Compound E
Stalk and foliage treatment agents such as 2019-2013 (referred to as ``2000'') have insufficient control effects on some harmful grasses such as dogfish, violets, etc., and when used in high doses to increase the effect, some causes chemical damage to crops.

[Problem to be solved by the invention]

An object of the present invention is to provide a herbicidal composition having a wider herbicidal spectrum at a lower dosage and which solves the problems of the prior art.

[Means and Effects for Solving the Problems] As a result of intensive studies by the present inventors to solve the above problems, the present inventors discovered that N-(3-chloro-4-isopropylphenyl)-2-methylpentanoic acid amide (hereinafter referred to as "compound A) or N-(3
-Chloro-4-isopropylphenyl)-2-methyl-
2 = The combination of pentenoic acid amide (hereinafter referred to as "compound B") and one or more of the sulfonylurea compounds of the above compounds C-E has excellent properties that cannot be expected simply from the respective chemical compounds for use in cars. The present invention has been completed based on the discovery that this can be achieved.

That is, the present invention provides an amide compound represented by the general formula (I):
8 represents a chlorine atom or -COCHi, and R3 represents a hydrogen atom or a methyl group. ) A herbicidal composition characterized by containing one or more sulfonylurea compounds represented by:

The amide compound represented by the general formula N) is a wheat-selective herbicide discovered by the present inventors, and is an excellent herbicidal compound exhibiting a new structure, a wide herbicidal spectrum, and high herbicidal activity (Japanese Patent Application No. 1986- No. 8763, 61-112
When 087) is mixed with one or more of the sulfonylurea compounds C to E represented by the general formula (■), the spectrum becomes broader and the activity is stabilized and improved.

In other words, the herbicidal composition of the present invention has a herbicidal effect on broad-leaved weeds such as staghorn grass and rye grass, which are serious problems in wheat fields, barley fields, and rye fields, at a lower dose than would be expected with a single agent. In addition, it shows an inhibitory effect on grass weeds at a lower dose than would be expected with a single agent, and has no phytotoxicity at all on wheat, barley, and rye.

Furthermore, it is also effective to add other herbicides for the purpose of enhancing the herbicidal effect of the herbicidal composition of the present invention and extending the treatment period.

The herbicidal composition according to the present invention can be mixed in a wide range of proportions in order to fully develop its mixing effect, but it is preferable that the amide compound represented by the general formula (I) and the general formula (
II) sulfonylurea compound represented by 1:
o,ooot to 0.1 (weight ratio), more preferably 1:0.001 to 0
．． The content is preferably 1 (weight ratio).

The amount of active ingredient when applied in fields depends on weather conditions,
Although it varies depending on the formulation form, application timing, application method, etc.
1 to 10 per are as the total application rate as a mixture
0 g is desirable, and 2 to 20 g per area is appropriate.

In the herbicidal composition of the present invention, the amide compound represented by the general formula (r) and the sulfonylurea compound represented by the general formula (II) may be used as a mixture without adding other ingredients, but the herbicidal composition In order to make it easier to use, it is common to add a carrier to the product. The herbicidal composition of the present invention can be formulated into emulsions, wettable powders, powders, granules, fine granules, etc. by methods well known in the art in accordance with general agricultural chemicals without any special conditions. It can be adjusted to any desired dosage form, such as oil radish, and can be used for various purposes depending on the purpose.

Carrier here means an inorganic or organic substance, synthetic or natural, which is incorporated to aid in the delivery of the active ingredient to the area to be treated and to facilitate storage, transport and handling of the active ingredient compound. .

Suitable solid carriers include clays such as montmorillonite and kaolinite; inorganic substances such as diatomaceous earth, clay, talc, vermiculite, gypsum, calcium carbonate, silica gel, and ammonium sulfate; and organic substances such as soybean flour, sawdust, and wheat flour. and urea.

Suitable heptads include aromatic hydrocarbons such as toluene, xylene, and cumene; paraffinic hydrocarbons such as kerosene and mineral oil; halogenated hydrocarbons such as carbon tetrachloride, chloroform, and dichloroethane; and acetone. , methyl ethyl ketone and other ketones; dioxane, tetrahydrofuran and other ethers; methanol, ethanol, propatool, ethylene glycol and other alcohols; dimethylformamide; dimethyl sulfoxide;
Examples include water.

Furthermore, in order to enhance the efficacy of the herbicidal composition of the present invention, various adjuvants may be used individually or in combination depending on the purpose, taking into account the dosage form of the preparation, the application situation, etc. For example, water-soluble bases such as lignin sulfonates for purposes of emulsification, dispersion, spreading, wetting, binding, stabilization, etc.; anionic surfactants such as alkylbenzene sulfonates; alkyl sulfate esters, polyoxyalkylene alkyl ether, polyoxyalkylene alkylaryl ether, polyoxyalkylene alkylamine,
Nonionic surfactants such as polyoxyalkylene alkylamides, polyoxyalkylene alkyl thioethers, polyoxyalkylene fatty acid esters, glycerin fatty acid esters, sorbitan fatty acid esters, polyoxyalkylene turubikun fatty acid esters, polyoxypropylene polyoxyethylene bloc polymers, etc. agents; lubricants such as calcium stearate and wax; stabilizers such as isopropylhydrodiene phosphate; methylcellulose,
Other additives such as carboxymethyl cellulose, casein, gum arabic, etc. are used. However, it goes without saying that the use is not limited to only these.

〔Example〕

Next, a method for synthesizing amide compound A and compound B represented by the general formula (2), which are new compounds, will be shown with specific examples.

Reference Example I N-(3-chloro-4-isopropylphenyl)-2-
Methylpentanoic acid amide (compound A) toluene 36II
+1, 3-chloro-4-isopropylaniline 1.0
g and 0.7 g of pyridine were added thereto, and further 0.9 g of 2-methylpentanoic acid chloride was added, followed by stirring at room temperature for 20 minutes. After separating the precipitated crystals by filtration, 70 ml of water was added to the filtrate and extracted with toluene.

The toluene solution was washed with a saturated aqueous solution of sodium bicarbonate and dried over anhydrous sodium sulfate. The crude crystals obtained by concentrating with an evaporator were recrystallized from methanol, and N-(3-chloro-4-isopropylphenyl)-2
-1.2 g of methylpentanoic acid amide was obtained. Yield: 3-
76% relative to chloro-4-isopropylaniline.

Reference example 2 N-(3-chloro-4-isopropylphenyl)-2-
Methyl-2-pentenoic acid amide (compound B) Dissolve 1.1 g of 3-chloro-4-isopropylaniline in 50 ml of toluene, and dissolve 0.7 g of triethylamine.
and 1.0 g of 2-methyl-2-pentenoyl chloride were added and stirred at room temperature for 2 hours. After filtering off the precipitated crystals, the filtrate was washed with a saturated aqueous solution of sodium bicarbonate and dried over anhydrous sodium sulfate. The oil obtained by concentrating with an evaporator was subjected to silica gel column chromatography (developing solvent: hexane/ethyl acetate-to: 1
(V/V)) to obtain 1.5 g of an oily product of N-(3-chloro-4-isopropylphenyl)-2-methyl-2-pentenoic acid amide. The yield was 87.5% based on 3-chloro-4-isopro and luaniline. The physical properties of the compounds obtained in Reference Examples 1 and 2 are shown in Table 1.

Next, the herbicidal composition according to the present invention will be specifically explained with reference to formulation examples.

Formulation Example 1 (Wettable powder) Compound A: 20 parts by weight, sodium alkylbenzene sulfonate = 2 parts by weight, polyoxyethylene alkylphenyl ether; 2 parts by weight, and Zikrite 076 parts by weight were thoroughly ground and mixed to prepare a wettable powder. I got it.

Formulation example 2 (hydrating powder) Compound B: 30 MN parts, polyoxyethylene alkylphenyl ether ammonium sulfate salt: 6 parts by weight, sodium naphthalene sulfonate formalin condensate: 2 parts by weight, sodium alkylbenzenesulfonate: 1 part by weight,
Polyvinyl alcohol = 2 parts by weight and diatomaceous earth: 5
9 parts by weight were thoroughly ground to obtain a wettable powder.

Formulation Example 3 (Flowable agent) Compound A: 40 parts 1 sodium naphthalene sulfonate formalin condensate: 3 parts by weight, sodium lignin sulfonate: 2 parts by weight, xanthan gum: 0.1 part by weight,
Deltofub (industrial disinfectant manufactured by Takeda Pharmaceutical Co., Ltd.):
0.1 parts by weight and 2 JltiL parts of polyoxyethylene alkyl phenyl ether were mixed with 52.8 parts by weight of water, and then finely ground using a sand grinder to obtain a flowable agent.

Formulation Example 4 (Dry Flowable Agent) Compound B: 60!1 parts, sodium alkylbenzenesulfonate = 5 parts by weight, and polypropylene glycol polyethylene glycol ether: 35 parts by weight were mixed,
The mixture was pulverized using a Jet-0-mizer to obtain a dry flowable agent.

Formulation Example 5 (Wettable powder) Compound A: 10 parts by weight, Compound C: 0.15 parts by weight, sodium alkylbenzene sulfonate: 2 parts by weight, polyoxyethylene alkylphenyl ether: 2 parts by weight, and dicrite 085.85 parts by weight. Parts by weight were thoroughly ground and mixed to obtain a wettable powder.

Formulation Example 6 (Flowable Agent) Compound B: 50 parts by weight, Part E: t, o parts by weight, sodium naphthalene sulfonate formalin condensate: 3 parts by weight, sodium ligninsulfonate: 2 parts by weight, xanthan gum: 0 1 part by weight and 2 parts by weight of polyoxyethylene alkylaryl ether were mixed with 41.9 parts by weight of water, and then finely ground using a sand grinder to obtain a flowable agent.

Formulation Example 7 (Dry flowable agent) Compound 8750 parts by weight, Compound D: 1. Cap 1 part, sodium alkylbenzenesulfonate: 2 parts by weight, polypropylene glycol polyethylene glycol ether: 1
8 parts by weight and 29 parts by weight of white carbon were mixed and pulverized using a Jet-0-mizer to obtain a dry flowable agent.

Test Example 1 (Field test) A 2m x 2.5m plot was taken in a field test area, and wheat, barley, and rye were sown as crops, and weeds were wild oat, sycamore, sycamore, japonica, japonica, shepherd's purse, chickweed, and chickweed. chamomile,
I sowed the grasshopper and the grasshopper. One month later, at the 8-leaf stage of wheat, a predetermined amount of the test compound was diluted with a wettable powder prepared according to the method described in Formulation Example 1 and Formulation Example 6 to a volume of water equivalent to 51 m/R, and applied uniformly to the stems and leaves. Fully processed.

Thirty days after the chemical treatment, the herbicidal effect on weeds and the degree of chemical damage to crops were investigated.

The results of the investigation were expressed by comparing the degree of chemical damage to crops and the herbicidal effect against weeds by comparing the emergence or growth of crops or weeds with the air-dried type in the untreated area according to the evaluation criteria below.

Evaluation Criteria Evaluation Air dry weight (%) vs. untreated area 7 11-15% 0 81-100% The test compounds are shown as the above abbreviations, Compounds A, B, C1D and E. Comparative Examples A, B, C , D and E used wettable powders prepared according to the method described in Formulation Example 1.

The results are shown in Table 2.

Table 2 Table 2 (Continued) From the results shown in Table 2, it is clear that the herbicide composition of the present invention can contain amide-based It has a complete control effect on broad-leaved weeds such as Prunus japonicus and Prunus japonicus, for which 5 g of the compound or 0.2 g of sulfonylurea compounds are insufficiently effective, and it also has a complete control effect on weeds of the grass family, such as Prunus japonicus, which are not effective with single agents. Suppression is also recognized against It is clear that this results in a significant synergistic effect and does not cause drug damage compared to the case where 5 g of an amide compound or 0.2 g of a sulfonylurea compound is used as a single agent per R.

〔Effect of the invention〕

As is clear from the above explanation, the herbicidal composition according to the present invention can be used as an agricultural herbicide against various weeds in wheat cultivation. It has an excellent weed control effect at low concentrations and has a wide herbicidal spectrum. Furthermore, it does not cause any chemical damage to wheat.

As described above, the herbicidal composition containing the amide compound and sulfonylurea compound according to the present invention has excellent properties and is useful as a herbicide.

Patent applicant: Mitsui Toatsu Kagaku Co., Ltd. Procedural amendment (voluntary) September 22, 1985 Commissioner of the Patent Office Kuro 1) Akio Yu 1, Indication of the case 1986 Patent Application No. 165472 2, Name of the invention: Weeding Composition 3, Relationship with the case of the person making the amendment Patent applicant address: 3-2-5 Kasumigaseki, Chiyoda-ku, Tokyo Betsu 4; Number of inventions increased by the amendment 6; Contents of the amendment (1) Page 6 of the specification , r D P X-15 in the 8th line
300J is corrected to rDPX-L5300J.

(2) On page 6, line 15, the words "herbicidal spectrum" are corrected to "herbicidal spectrum."

(3) On page 19, in the second line from the bottom, the word "showed" is amended to "shown."

(4) On page 22, line 11, the phrase "ro, used in 2g" is corrected to "ro, used in 2g."

Claims (7)

[Claims] (1) General formula (I): ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (I) (In the formula, R_1 is ▲There are mathematical formulas, chemical formulas, tables, etc.▼ or ▲There are mathematical formulas, chemical formulas, tables, etc.▼ ) An amide compound represented by the general formula (II): ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (II) (In the formula, R_2 represents a chlorine atom or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, R_3 represents a hydrogen atom or a methyl group.) A herbicidal composition characterized by containing one or more sulfonylurea compounds represented by (2) The amide compound represented by the general formula (I) is N-
(3-chloro-4-(isopropylphenyl)-2-methylpentanoic acid amide, a sulfonylurea compound represented by the general formula (II) is 2-chloro-N-(4
-methoxy-6-methyl-1,3,5-triazine-2
2. The herbicidal composition according to claim 1, wherein the herbicidal composition is 1:0.001 to 0.1 (weight ratio) of 1:0.001 to 0.1 (weight ratio). (3) The amide compound represented by the general formula (I) is N-
(3-chloro-4-(isopropylphenyl)-2-methylpentanoic acid amide, and the sulfonylurea compound represented by the general formula (II) is methyl 2-[3-(4-
Methoxy-6-methyl-1,3,5-triazine-2-
2. The herbicidal composition according to claim 1, wherein the herbicidal composition is ureidosulfonyl]benzoate in a ratio of 1:0.001 to 0.1 (weight ratio). (4) The amide compound represented by the general formula (I) is N-
(3-chloro-4-(isopropylphenyl)-2-methylpentanoic acid amide, and the sulfonylurea compound represented by the general formula (II) is methyl 2-[3-(4-
Methoxy-6-methyl-1,3,5-triazine-2-
yl)-3-methylureidosulfonyl]benzoate in a ratio of 1:0.001 to 0.1 (weight ratio). . (5) The amide compound represented by the general formula (I) is N-
(3-chloro-4-(isopropylphenyl)-2-methyl-2-pentenoic acid amide, and the sulfonylurea compound represented by the general formula (II) is 2-chloro-N-
(4-methoxy-6-methyl-1,3,5-triazin-2-yl-aminocarbonyl)benzenesulfonamide, and their ratio is 1:0.001 to 0.1 (weight ratio).
Claim 1 characterized in that it contains in a proportion of
The herbicidal composition described in . (6) The amide compound represented by the general formula (I) is N-
(3-chloro-4-isopropylphenyl)-2-methyl-2-pentenoic acid amide, and the sulfonylurea compound represented by the general formula (II) is methyl 2-[3-(
4-methoxy-6-methyl-1,3,5-triazine-
2-yl)ureidosulfonyl]benzoate,
The herbicidal composition according to claim 1, characterized in that the herbicidal composition contains them in a ratio of 1:0.001 to 0.1 (weight ratio). (7) The amide compound represented by the general formula (I) is N-
(3-chloro-4-isopropylphenyl)-2-methyl-2-pentenoic acid amide, and the sulfonylurea compound represented by the general formula (II) is methyl 2-[3-(
4-methoxy-6-methyl-1,3,5-triazine-
2-yl)-3-methylureidosulfonyl] benzoate, and contains them in a ratio of 1:0.001 to 0.1 (weight ratio). Composition.