JPS6317809A - Herbicide composition - Google Patents

Abstract

PURPOSE:A herbicide composition that contains, as active ingredients, a combination of a pyrone-3-carboxamide derivative with a known compound with herbicidal activity, thus enabling perfect control against all kinds of weeds by only one application with extremely reduced chemical injury and low toxicity to man and animals. CONSTITUTION:The objective composition contains, as active ingredients, a combination of a compound of the formula [R1, R3 are 1-11C alkyl, alkenyl, alkinyl, aralkyl, aryl which may be substituted; R2 is H, halogen 1-11C alkyl, aryl; or R2 and R3 may incorporate to form (CH2)m (m is 3, 4); A is H, halogen, CN, NO2, NH2, alkyl, OH, alkoxy, aryloxy] with another compound selected from 7 compounds including i) 2-chloro-2',6'-diethyl-N-methoxymethyl acetanilide, ii) N-(1-ethylpropyl)-3,4-dimethyl-2,6-dinitroaniline, iii) 3-(3,4-dichlorophenyl)-1,1- dimethylurea and others, at a weight ratio of 1:(0.2-5).

Description

DETAILED DESCRIPTION OF THE INVENTION () General Field of Application The present invention comprises at least one type of pyrone-3-carboxamide derivative and a known compound having herbicidal activity (described in detail below). The present invention relates to a herbicidal composition containing the present invention as an active ingredient.

(Prior art) Conventionally, a compound belonging to pyrone-3-carboxamide,
Furthermore, the herbicidal composition shown in the present invention is a novel combination described in the literature, and of course there is no text mentioning its unique herbicidal effect. There is no +'tiK either.

(The problem that Komei is trying to solve) Currently, many types of herbicides have been banned in agriculture.
Widely and commonly used. Cotton is an important crop that is cultivated over a large area worldwide and is widely cultivated as a craft crop. Many herbicides for cotton have also been developed as labor-saving alternatives to manual weeding. However, the grasses found in agricultural land are extremely diverse and come in many varieties.
1i1- All German herbicides that satisfy the conditions of a wide herbicidal spectrum and no chemical damage can be said to be jH%.

The present invention was developed in view of these problems with conventional herbicides, and continues the search for a herbicide that can be used for rotation to completely exterminate all T4 plants, has extremely minimal phytotoxicity, and has low toxicity to humans and animals. As a result, it was discovered that the above-mentioned problems could be improved by blending and using together two types of herbicides each having a different herbicidal action as described in the present invention, and the present invention was completed.

Means for Solving Problem C) The present invention provides at least one compound represented by the following formula (I) and at least one compound selected from the following known compounds B-1 to B-7. The present invention relates to a herbicidal composition containing a type of herbicide as an active ingredient.

In the formula, R1 and R3 are the same or different and are an alkyl group of 01 to C11, a lower alkenyl group, a lower alkynyl group, a cycloalkyl group, a lower alkoxyalkyl group, an optionally substituted aralkyl group, a halogenated alkyl group, a substituted An optional aryl group or a 5- or 6-membered heterocyclic group,
R2 represents a hydrogen atom, a halogen atom, a C1-C11 alkyl group, an optionally substituted aryl group, or an optionally substituted aralkyl group, or R2 and R3 together represent -CC
H2) m- (m is 3 or 4), A represents a hydrogen atom, or one or more than two benzene rings, and if two or more are the same or different, It means a halogen atom, a cyano group, a 21-ring group, an amino group, a lower alkyl group, a halogenated lower alkyl group, a hydroxyl group, a lower alkoxy group, an aryloxy group, a carboxy group, or a lower alkoxycarbonyl group, respectively.

B-12-Chloro-2',6'-diethyl-N-methoxymethylacetanilide B-2a,α,α-trifluoro-2,6-sinitro N,N-dipropyl-p-toluidine B-33,5-dinitro -N4. N4-dipropylsulfanilamide B-4N-(1-ethylpropyl)-3,4-dimethyl-2,6-sinitroaniline B-51,1-dimethyl-3-(α,α,α-trifluorom -) lyl) urea B-63-(3,4-dichlorophenyl)-1,1-dimethylurea B-73-(3,4 dichlorophenyl)-1-me-1-xy-1-methylurea Weed control of the present invention Among the active ingredients of the agent composition, compound B-1
Compound B-7 is a substance known as a herbicide for field use. To explain in more detail, Compound B-1 to Compound B-4 are herbicides belonging to the so-called dinitroaniline family, and are highly effective against grasses such as grasses such as grasses and broad-leaved plants such as cotton and soybeans. Although these compounds are known to be highly safe for crops, they all have the drawback of being less effective against annual broad-leaved weeds. .

Next, compound B-5, compound B-6 and compound B-7 are
It is a herbicide that belongs to the so-called urea family, and is extremely effective against broad-leaved weeds, and is highly safe against many broad-leaved crops such as cotton and soybeans, and many grass crops such as corn. It has been known. However, both compounds have the drawback of being less effective against annual rice weeds such as field weeds.

On the other hand, among the active ingredients of the herbicide composition of the present invention, formula (I
) (hereinafter referred to as compound A) is -
It is effective against older grass weeds and broad-leaved weeds, and has a long residual effect with little damage to broad-leaved crops such as cotton and soybeans, and many grass crops such as corn. It has the following characteristics.

The present inventors have found that Compound A and Compounds B-1 to B-7, which each have the above-mentioned drawbacks, are used in a mixture in an appropriate ratio to compensate for the drawbacks of using each alone, and to achieve extremely significant results. The herbicidal spectrum and suitable period of use are greatly expanded by the t[] slag action, and as a result, the herbicidal spectrum and suitable period of use are greatly expanded. They discovered that the spraying has excellent weeding effects over the entire cotton growth period, and has no chemical damage to cotton.

That is, when compound A is mixed with compound B-1, compound B-2, compound B-3, or compound B-4,
The latter has a synergistic herbicidal effect on annual broad-leaved weeds such as purslane and whiteweed, which are less effective when used alone, and compound A and compound B-5, compound B-6, or compound B-7
When used in combination, it has a synergistic herbicidal effect on annual grass weeds such as wild grass and foxtail grass.In addition, in any combination, the safety of cotton is not compromised and no problematic chemical damage occurs. .

Among the active ingredients of the herbicidal composition of the present invention, most of the compounds represented by formula (I) (compound A) are new substances, and can be produced, for example, by the method shown in the following production example. can.

Production Example (Method A) (R1 and A are the same as defined in formula (I), R4 is dialkylamino, n is an integer of O to 6.) This method is based on formula (II). ) and the compound represented by formula (II') and diketene in a suitable solvent (e.g. toluene,
xylene, etc.) at a temperature of -20 to 130°C. This is a method for synthesizing a compound in which R2 is a hydrogen atom and R3 is a methyl group.

(Method B) (R1 and A are the same as defined in formula (I), and R5 represents an alkyl group, a cycloalkyl group, an aryl group, or a ring group consisting of 5"). ) and diketene in a suitable solvent (e.g. toluene,
xylene, etc.) at a temperature of -20 to 130°C. This is a method for synthesizing a compound in which R2 is a hydrogen atom and R3 is methyl, (-(Method C)
) This method combines the compounds represented by formula (II) and formula (II') and the compound represented by formula (IV) into j! Koshiki medium (R2 and R3 are the same as defined in formula (I),
Are R6 and R7 hydrogen atoms, alkyl groups, or phenyl? 11
; or when R6 and R7 are both alkyl groups, a cycloalkyl group may be formed. ) Alternatively, the reaction is carried out in a suitable solvent (toluene, benzene, mesitylene, etc.) under heating (for example, 100 to 170°C).

(Method D) (R2 and R3 are the same as defined in formula (I), and
7 is the same as the definition of formula (1 for , solvent-free or appropriate solvent (toluene, benzene, mesitylene, etc.)
The reaction is carried out under medium heating (for example, 100 to 170°C).

(Method E) (R2 and R3 are the same as defined in formula (I), and R8 means a lower alkyl group.) This method and a compound represented by formula (V) in an inert solvent (for example, xylene, mesitylene, etc.) in the presence of a molecular sieve.

Examples of Compound A obtained by the above method are shown in Table 1 (hereinafter, specific examples of Compound A are indicated by compound No. in Table 1).

The unique herbicidal effect related to the present invention is observed in a fairly wide range of mixing ratios, but the weight ratio of Compound A and Compounds B-1 to B-7 is 1:0.1 to 10 (more preferably 1:1). It is preferable to mix it so that it becomes 0.2-5). The herbicide composition of the present invention comprises compound A and compound B.
Although the active ingredient compounds of -1 to Compound B-7 may be used as they are, they are generally mixed with solid carriers, liquid carriers, surfactants, and other formulation auxiliaries to form wettable powders, emulsions, etc. Formulate.

These preparations contain 10 to 80% of the herbicidal composition of the present invention as a total of the active ingredients of Compound A and Compounds B-1 to B-7 in wettable powders and 10 to 5% in emulsions.
It is preferable that the content is 0% (all percentages are by weight).

Solid carriers used in formulations include fine powders or granules such as kaolin, bentonite, clays, talc, diatomaceous earth, gicrite, zeolite, pyrophyllite, synthetic silicon oxides, and calcium carbonate, and liquid carriers. for,
Aromatic hydrocarbons such as xylene and methylnaphthalene, alcohols such as ethanol, isopropanol, ethylene glycol, and methyl cellosolve, ketones such as acetone, isophorone, and cyclohexanone, vegetable oils such as soybean oil and cottonseed oil, dimethylformamide, dimethyl Surfactants used for dispersion, LL formation, etc. include sulfoxide, acetonitrile, water, etc. Polyoxyethylene alkyl ether, polyoxyethylene alkylaryl ether, polyoxyethylene fatty acid ester, sorbitan fatty acid ester, polyoxy Nonionic surfactants such as ethylene sorbitan fatty acid ester, polyoxyethylene polyoxypropylene block polymer, anionic surfactants such as alkyl sulfate salts, alkyl sulfonates, alkylaryl sulfonates, polyoxyethylene alkyl sulfate salts, etc. There are drugs etc.

Formulation adjuvants include lignin sulfonates, alginates, polyacrylates, polyvinyl alcohol, vegetable gums, carboxymethyl cellulose (CMC), hydroxyethyl cellulose (HEC''), and the like.

(Example) Next, formulation examples will be shown, but the present invention is not limited to these. In addition, parts indicate parts by weight.

Formulation Example 1 Wettable powder Compound No. A-2520 parts, Compound No. B-720
part, 40 parts of talc, 15 parts of bentonite, Tsurupol-
Two parts of 9047 (manufactured by Toho Chemical) and three parts of Tsurupol 5039 (same as above) were thoroughly ground and mixed to obtain an irrigation agent.

Formulation Example 2 Emulsion Compound No., A-3015 parts, Compound No., B-315
20 parts of xylene, 42 parts of dimethylformamide, 8 parts of polyoxyethylene alkylphenyl ether:
Mix thoroughly to obtain a 1L formulation.

The wettable powders and emulsions prepared as described above are usually diluted with water, and the granules are used as they are by spraying on the soil or on foliage and on the soil.

Furthermore, the herbicidal composition of the present invention may be used in combination with other insecticides, acaricides, nematicides, fungicides, herbicides, plant growth regulators, fertilizers, or soil conditioners as necessary. can.

Next, the usefulness of the herbicide composition of the present invention will be shown in Examples.

Example: Herbicidal effect and phytotoxicity test 3 A plastic case measuring 26 cm x 26 cm and 3 cm deep was filled with field soil, and weed seeds (wildflower, foxtail grass, crabgrass, purslane, white grass) and crop seeds (cotton) were sown to a depth of 1 to 2 cm. The plants were covered with soil and grown for 14 days. after that,
The herbicidal composition of the present invention, made into an emulsion according to Formulation Example 2, was diluted with a predetermined amount of water and uniformly sprayed over the entire foliage group from above the plant using a small sprayer to a predetermined amount.

After 150 days of chemical treatment, the herbicidal effect and phytotoxicity were evaluated according to the following criteria, and the results are shown in Tables 2 and 3.

Claims (1)

[Claims] Formula (I): [In the formula, R_1 and R_3 are the same or different and C_1 to C
_1_1 alkyl group, lower alkenyl group, lower alkynyl group, cycloalkyl group, lower alkoxyalkyl group, optionally substituted aralkyl group, halogenated alkyl group, optionally substituted aryl group, or 5- or 6-membered heterolog A ring group, R_2 is a hydrogen atom, a halogen atom, C_1
~C_1_1 alkyl group, optionally substituted aryl group, or optionally substituted aralkyl group, or R_
2 and R_3 together -(CH_2)m-(m is 3 or 4
), A represents a hydrogen atom, or one or more substituents on the benzene ring, and in the case of two or more substituents, they are the same or different and are a halogen atom, a cyano group, a nitro group, an amino group, a lower Alkyl group, halogenated lower alkyl group,
Hydroxy group, lower alkoxy group, aryloxy group,
It means a carboxy group or a lower alkoxycarbonyl group, respectively. ] and at least one compound selected from the following known compounds B-1 to B-7 as active ingredients. A herbicide composition. B-1 2-chloro-2',6'-diethyl-N-methoxymethylacetanilide B-2 a,a,a-trifluoro-2,6-dinitro-N,N-dipropyl-para-toluidine B-3 3,5-dinitro-N4,N4-dipropylsulfanilamide B-4 N-(1-ethylpropyl)-3,4-dimethyl-2,6-dinitroaniline B-5 1,1-dimethyl-3-( a,a,a-trifluoro-meta-tolyl)urea B-6 3-(3,4-dichlorophenyl)-1,1-
Dimethylurea B-7 3-(3,4dichlorophenyl)-1-methoxy-1-methylurea