JPS5948404A - Herbicide for paddy field - Google Patents

Abstract

PURPOSE:A herbicide for paddy fields, containing ethyl 2-methyl-4-chlorophenoxybutyrate and an alpha,alpha-dimethylphenylacetanilide derivative, capable of completely controlling annual weeds, etc. even in a low dose, having a large width of period suitable for application, and exhibiting the efficacy for a long term. CONSTITUTION:A herbicide containing ethyl 2-methyl-4-chlorophenoxybutyrate and an alpha,alpha-dimethylphenylacetanilide derivative of the formula (X is halogen, lower alkyl, lower alkoxyl or alkenyloxy; n is an integer 0-3) as active constituents, preferably in amounts of 0.03-5.0pts.wt., preferably 0.05-1.0pts.wt., ethyl 2-metyl-4-chlorophenoxybutyrate and 1pt.wt. compound of the formula. In application, the resultant mixture may be directly used, but usually an adjuvant is formulated together to give the aimed herbicide. The herbicide is preferably used in the form of a granule. The amount of the herbicide to be used is 200-500g, preferably 300-400g, based on one are.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a herbicide for rice fields with improved action.

The present inventors have synthesized novel α,α-dimethylphenylacetic acid anilide derivatives, and demonstrated that these compounds are effective against warm-blooded animals (acute oral m9/k1 or more) and aquatic animals (acute TL
It has low toxicity against m 24 I(511)T)m or higher), has excellent selectivity for cultivated plants, and exhibits particularly excellent herbicidal and growth-inhibiting effects on wild grasses and snails. (See Japanese Patent Application No. 56-29519).

However, this compound has drawbacks such as a narrow range of suitable treatment periods, being sufficiently effective only against weeds from before to just after emergence, and unsatisfactory efficacy against broad-leaved weeds. As a result of further searches, it was discovered that an excellent herbicide could be obtained by using a combination of an α,α-dimethylphenylacetic acid anilide derivative and ethyl 2-methyl-4-chlorophenoxybutyrate.

The present invention relates to ethyl 2-methyl-4-chlorophenoxybutyrate (hereinafter abbreviated as MCPBE) and the general formula c, where χ is a norogen atom, a lower alkyl group, a lower alkokene group, or an alkenyl group, and n is 0 to 6. )
This herbicide for rice fields is characterized by containing an α,α-dimethylphenylacetic acid anilide derivative represented by the following as an active ingredient.

In the compounds of formula I, when n is 2 or more -L, it may be individual or the same or different.

When the compound of formula (■) is used in combination with MCPI, it exhibits a remarkable synergistic effect against various young weeds and perennial Cyperaceae weeds such as bulrushes and cyperus, which cannot be expected to be sufficiently controlled by each agent alone, and can be used at low treatment rates. These weeds can be completely controlled. In addition, the range of suitable treatment periods is expanded to an extent that cannot be predicted from each single agent, and the weed suppression period is also significantly extended, making it possible to prevent weed growth for a long period of time.

Examples of the α,α-dimethylphenylacetic acid anilide derivative of formula 1 used in the herbicide of the present invention include the following compounds. Note that the numbers in parentheses indicate compound numbers.

(1) N-phenyl-α,α-dimethylphenylacetamide (2) N-(6-chlorophenyl)-α,α-dimethylphenylacetamide (3) N-(3-methylphenyl)-α,α-dimethylphenyl Acetamide (4) N-(3-ethylphenyl)-α,α-dimethylphenylacetamide (5) N-(4-ethylphenyl)-α,α-dimethylphenylacetamide (6) N-(“1s-n- propylphenyl)-α
, α-dimethylphenylacetamide (7) N -(4-n-propylphenyl)-α, α
-dimethylphenylacetamide (8)N-43-isopropylphenyldimethylphenylacetamide (9)N-(4-isopropylphenyl)-α,α-dimethylphenylacetamide (10)N-(6-n-butylphenyl)-α
, α-dimethylphenylacetamide (11) N - (6-secondary butylphenyl)-α,
α-dimethylphenylacetamide (12) N - (4-secondary butylphenyl)-α,
α-dimethylphenylacetamide (15)N-(5-methoxyphenyl)-(χ,
α-Dimethylphenylacetamide (14) N - (6-alkenyloxi/phenyl)
-α,α-dimethylphenylacetamide (15)N
- (6-methyl-6-methoxyphenyl)-α,α
-dimethylphenylacetamide (16)N - (
2-Methoxy-5-ethylphenyl)-α,α-dimethylphenylacetamide (17) N-(2-methoxy-5-rl-propylphenyl)-α,α-dimethylphenylacetamide The herbicide of the present invention includes each drug. Although the mixture may be used as it is, it is preferable to formulate it into powders, wettable powders, emulsions, etc., especially granules, by a method commonly used in the agricultural chemical manufacturing field, usually using an adjuvant at °C. Agrochemical auxiliaries include diluents such as solvents, fillers, carriers, surfactants, emulsifiers, dispersants, wetting agents, fixing agents, stabilizers, and the like. Examples of solvents include water, benzene, toluene, xylene, and alcohols such as evamethyl 7/L' co-/
L/, ethyl alcohol, furoyl ethylene glycol, etc., ketones such as acetone, cyclohexane, isophorone, etc., esters such as ethyl acetate, amyl acetate, etc., amides such as dimethylformamide, dimethylacetamide, etc., or mixtures thereof.

Examples of surfactants include anionic surfactants such as sodium lauryl sulfate and alkylaryl sulfonates, cationic surfactants such as alkyldimethylbenzene ammonium chloride and lauryl amine, and nonionic surfactants such as polyoxyethylene alkylaryl. Examples include ethers, polyoxyethylene fatty acid esters, polyoxyethylene sorbitan monolaurate, and amphoteric surfactants.

Examples of the fixing agent and stabilizer include sodium alginate and polyvinyl alcohol.

The herbicide of the present invention contains MCP per 1 part by weight of the compound of formula I.
0.06 to 5.0 parts by weight of BE, preferably 0.05
They are used together in a proportion of ~1.0 parts by weight. The content of these active ingredients depends on the form of the preparation, application method, purpose, timing, location,
It can be changed appropriately depending on the situation of weed growth. The herbicide of the present invention can also be used in combination with other agricultural chemicals such as insecticides, acaricides, fungicides, plant growth regulators, fertilizers, and the like.

It is preferable that the herbicide of the present invention be applied by a commonly used application method, such as waterlogged soil treatment. The amount used is 2° to soog per are, preferably 300 to 400 g.

In the examples below, parts refer to weight.

Example 1 Compound (4) so part MC
PBE 5 parts Sodium dodecylbenzenesulfonate 2 parts Sodium ligninsulfonate 6 parts Diatomaceous earth
Grind and mix 40 parts of the above ingredients to form a wettable powder 1
Get 00 copies.

Example 2 Compound (6 parts MCPBE)
6 parts polyoxyalkylene alkyl allyl ether 10 parts polyoxyethylene alkyl 6 parts allyl ether sulfate xylene 54 parts The above components were uniformly mixed to obtain 100 parts of an emulsion.

Example 6 Compound (6) 5 parts 10 CPBT 0.5 parts Sodium alkylbenzenesulfonate 2 parts Polyvinyl alcohol 0.5 parts Clay
60 parts bentonite 6
After pulverizing and mixing 2 parts of the above ingredients, an appropriate amount of water is added and kneaded, granulated using a granulator and dried to obtain 100 parts of granules.

Test Example 1 A 11,500a pot (two-section system) was filled with sandy loam soil, and after fertilization, flooding, and plowing, 5 tubers of germinated Cyperus japonica were planted per pot. Planting was carried out on the second day after planting (immediately after emergence and on the 14th day at the 3-leaf stage), and a predetermined amount of the hydrating powder of each test drug produced according to Example 1 was added to a water depth of 6 cr.
Flooded soil was treated under these conditions. On the 35th day after treatment, the remaining grass was removed and air-dried. was measured to determine the grass ratio (%) relative to the untreated area. The results are shown in Tables 1-6.

Test Example 2 A 1/10000a porcelain pot was filled with sandy loam soil, and after flooding and plowing, a predetermined amount of the aqueous phase agent of each test agent produced according to Example 1 was applied to the flooded soil at a water depth of 2 crn. 'did.

After the treatment, 20 germinated firefly seeds were sown per pot at a depth of about 0.5σ. During the exam period,
The water depth was maintained at 1 to 2 z, and weeds that remained in the mouth for 4 weeks after sowing were removed, air-dried weight was measured, and the grass rate (%) relative to the untreated plot was calculated, and the index was determined according to the following criteria. The results are shown in Table 4.

Test Example 3 50 cm x 50 cm x 5 installed outdoors
Fill a 0 cm concrete pot with sandy loam, and after fertilizing, flooding and puddling, weed seeds and tubers are placed at a depth of 0 to 1 cm.
The rice seedlings were transplanted to a depth of about 2 ctn. On the 12th day after transplantation (2nd leaf stage of wildflowers), the granules of each test agent produced according to Example 6 were treated with flooded soil at a water depth of 4 to 5 cr. The test was conducted in two plots, and on the 60th day after chemical treatment, the remaining weeds were pulled out and their air-dried weight was measured to determine the percentage of weeds dying compared to the untreated plot. The results are shown in Table 5.

Procedural amendment (voluntary) December 6, 1980 Kazuo Wakasugi, Commissioner of the Patent Office 3. Relationship with the case of the person making the amendment Patent applicant address (name) 4. Agent 5. Date of amendment order 6. , the following corrections are made in the specification of the written amendment (Patent Application No. 5B080 of 1982), as shown in the attached written correction for the number of inventions to be increased by the amendment.

1. "Specification of Japanese Patent Application No. 56-29319" in the 6th line from the bottom of the second page is changed to "Japanese Patent Application Laid-Open No. 57-144203".

2. Change "alkenyl group" in the bottom two lines of page 2 I to "alkenyloxy group".

6. Add the following sentence between lines 4 and 6 from the bottom of page 6.

"As mentioned above, the compound of formula 1 is an early herbicide for paddy rice that exhibits an appropriate control effect when used at any time from before to just after weed emergence.On the other hand, MCPBE has plant hormone action. It is an absorption type herbicide and has a unique herbicidal effect on Cyperaceae and broad-leaved weeds.

However, if MCPI alone is used within the dosage range that is safe for paddy rice, it is difficult to sufficiently control these grass species, and it is less effective against grass weeds. 4. In the 6th line from the bottom of page 6, in front of "compound of formula I", add "having different properties as described above".

5. 5th ``Alkenyloxyphenyl'' in the 4th line from the bottom is changed to ``allyloxyphenyl''.

6. On the last line of page 6, add the following sentence after "Mixtures are included."

"Bulking agents or carriers include, for example, bentonite, talc, clay, diatomaceous earth, calcium carbonate, etc., or mixtures thereof." Z, page 8, lines 4-6, "The amount used is ------- -- is amended as follows.

``The amount used is usually 10 to 5 as the active ingredient per 10 ares.
00I, preferably 15-600g. 8. The entire text of the claims from line 4 on page 1 to line 3 on page 2 is revised as shown in the attached sheet.

“Claim 1, Ethyl 2-methyl-4-chlorophenoxybutyrate and the general formula (wherein ) A herbicide for chickenpox characterized by containing an α-dimethylphenylacetic acid anilide derivative as an active ingredient.

2. α,α-dimethylphenylacetic acid anilide derivative, N-(3-ethylphenyl)-α,α-dimethylphenylacetamide, li-(3-n-propylphenyl)-α,α-dimethylphenylacetamide or N −
The herbicide for rice fields according to claim 1, which is (4-■l-propylphenyl)-α,α-dimethylphenylacetamide. ”

Claims (1)

[Claims] 1. Ethyl 2-methyl-4-chlorophenoxybutyrate and the general formula (in the formula, X is a halogen atom, a lower alkyl group, a lower alkoxy group, or an alkenyl group, and TI represents an integer from Q to 3)
A herbicide for rice fields, characterized by containing an α,α-dimethylphenylacetic acid anilide derivative represented by the following as an active ingredient. 2. The α,α-dimethylphenylacetic acid anilide derivative is N-(6-nitylphenyl)-α,α-dimethylphenylacetamide, N(3-n-propylphenyl)-α,α-dimethylphenylacetamide or N-
The herbicide for rice fields according to claim 1, which is (4-n-propylphenyl)-α,α-dimethylphenylacetamide.