JP3347778B2 - Herbicide composition - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to the formula (1)

[0002]

Embedded image

(Wherein R ₁ and R ₂ are the same or different and represent a lower alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, or R ₁ and R ₂ together with the nitrogen atom to which they are bonded) Represents an azacycloalkane having 4 to 6 carbon atoms, wherein A is a group represented by the formula (2):

[0004]

Embedded image

Equation (3)

Embedded image

Equation (4)

Embedded image

Or equation (5)

Embedded image

Wherein X is a lower alkyl group which may be substituted with a hydrogen atom or a hydroxyl group, or a cycloalkyl group, an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyl group, a phenoxy group, a benzyl group, an α -Hydroxybenzyl group, halogen, nitro group,
Represents an amino group or a trifluoromethyl group, m is 0,
A number of 1, 2 or 3 and n represents a number of 0, 1 or 2) and a triazole compound represented by the formula (6):

[0009]

Embedded image

1- (2-chloroimidazo [1,2- a ] pyridin-3-ylsulfonyl) -3-
The present invention relates to a herbicide composition obtained by mixing (4,6-dimethoxy-2-pyrimidinyl) urea as an active ingredient.

[0011]

2. Description of the Related Art A compound represented by the formula (1) is disclosed in
No. 1481 discloses that it exhibits an excellent herbicidal effect on foxtails and the like. Also, 1
-(2-chloroimidazo [1,2- a ] pyridine-3-
Ilsulfonyl) -3- (4,6-dimethoxy-2-pyrimidinyl) urea is a compound described in JP-A-64-38091 and has been shown to be effective against broadleaf weeds and perennial weeds. I have.

The compound represented by the formula (1) is
For the broadleaf weeds and perennial weeds that have grown, their herbicidal effect is weak, and a large amount of spraying is required to obtain a sufficient effect.

On the other hand, 1- (2-chloroimidazo [1,2
-A ] pyridin-3-ylsulfonyl) -3- (4,6
-Dimethoxy-2-pyrimidinyl) urea has a problem in that herbicidal effect is weak against growing rice flour, and that increasing the amount of the drug causes phytotoxicity to rice.

In recent years, the occurrence of perennial weeds such as Tainubie, Spodoptera litura, Firefly, and Urikawa, which are strongly harmful weeds in paddy fields, has become a problem, and application of a herbicide having a narrow herbicidal spectrum or application of a small amount of herbicide has been a problem. Control cannot be expected. For this reason, the same or different herbicides must be used several times or in large amounts, and many problems such as phytotoxicity to rice and soil residue as well as labor and cost are mentioned. .

[0015]

The inventors of the present invention have conducted intensive studies to solve the above-mentioned problems, and as a result, the following expression (1) is obtained.
And 1- (2-chloroimidazo [1,2
-A ] pyridin-3-ylsulfonyl) -3- (4,6
-Dimethoxy-2-pyrimidinyl) urea surprisingly gives a broader herbicidal spectrum, each of which exceeds the application range obtained by the single agent application, and also shows a significant herbicidal effect at low doses. Without harm to
The inventor has found that a synergistic effect that could not be expected at all was observed, such as a long-term herbicidal effect, and based on this, the present invention was completed.

The compound represented by the formula (1), which is one of the active ingredients of the composition of the present invention, is, for example, a compound represented by the formula (7)

Embedded image

Wherein A and n are the same as defined above, and a compound of the formula (8)

Embedded image

(Wherein Y is a halogen atom, R ₁ and R ₂ are the same as described above), and if necessary, oxidized with a suitable oxidizing agent. The details of the method for synthesizing the compound represented by the formula (1) are described in detail in the above-mentioned JP-A-2-1481.

In the triazole compound represented by the formula (1) used in the present invention, a preferable specific example is a compound represented by the formula (9)

Embedded image The compound shown by these is mentioned.

Further, 1- (2) used in the present invention
-Chloroimidazo [1,2- a ] pyridin-3-ylsulfonyl) -3- (4,6-dimethoxy-2-pyrimidinyl) urea is produced according to the method disclosed in JP-A-64-38091. be able to.

The composition of the present invention comprises a novel combination which has not been described in the literature, and of course, there is no literature which mentions its specific efficacy enhancement.

The herbicidal action of the herbicidal composition of the present invention is observed in a wide range of mixing ratio, and 1- (2-chloroimidazo [1,2] is added to 1 part by weight of the compound represented by the formula (1). −
a ] pyridin-3-ylsulfonyl) -3- (4,6-
Dimethoxy-2-pyrimidinyl) urea at 0.01 to 10
The herbicidal composition of the present invention can be produced by mixing in parts by weight.

The herbicidal composition of the present invention thus produced can provide a high herbicidal effect by soil treatment before and after germination of weeds, and can be safely used without substantially damaging rice. You can do it.

The herbicidal composition of the present invention may be sprayed on the drug substance itself, but may be mixed with various solid or liquid carriers used in general pesticide preparations for more convenient use. , Wettable powders, emulsions, oils, powders, granules, flowables and the like. Further, the herbicidal composition of the present invention may contain an auxiliary agent such as a dispersant, a diluent, an emulsifier, a spreading agent, a wetting agent, an adsorbent, a thickener, an antifoaming agent, and an antifreezing agent. Good.

The carrier mentioned here may be either a solid or a liquid, or a combination thereof. Carriers that can be used include talc, clay, bentonite, kaolin, diatomaceous earth, calcium carbonate, charcoal, starch, gum arabic, water, alcohol, kerosene, naphtha, xylene,
Cyclohexane, methylnaphthalene, benzene, acetone, dimethylformamide, glycol ether, N-
Methylpyrrolidone and the like.

Examples of the adjuvant include polyoxyethylene alkyl phenyl ether, polyoxyethylene sorbitan monooleate, ethylene oxide propylene oxide copolymer, lignin sulfonate, sorbitan ester, soaps, sulfated oils, alkyl sulfate esters. , Petroleum sulfonates, dioctyl sulfosuccinate salts, alkylbenzene sulfonates, aliphatic amine salts, quaternary ammonium salts, alkylpyridinium salts, alkyldimethyl betaine, alkylaminoethylglycine, polyglycol sulfate, alkylamine sulfonic acid, Examples include isopropyl phosphate, carboxymethyl cellulose, polyvinyl alcohol, hydroxypropyl cellulose, ethylene glycol, xanthan gum and the like.

In the formulation, the mixing ratio of the composition of the herbicidal composition of the present invention is 0.05% by weight of the active ingredient.
Can be freely selected within the range of ~ 95%, preferably 0.5% ~ 70% of the active ingredient, 1 ~ 99% of the carrier,
It is preferable that the preparation contains 40 to 90%, and 0 to 20%, preferably 1 to 7% of an auxiliary agent. In addition, by mixing with other herbicides, plant growth regulators, pesticides, fungicides, pesticides and fertilizers such as miticides,
A wider effect can be expected.

When the herbicidal composition of the present invention is actually used, it is important to appropriately select the amount to be used according to the time of use, weather conditions, method of use, dosage form, place of use, target weed, target crop, and the like. It is a category that can be freely achieved by a trader based on their experience. Generally, the dosage used of the herbicidal composition of the present invention is generally 5 to 500 per 10 ares.
g, preferably 10 to 300 g.

[0029]

The present invention will be specifically described below with reference to Test Examples and Preparation Examples. Test Example 1 A paddy field soil was filled into a 1/5000 arel Wagner pot, water was added to the paddy field, paddy was planted, and seeds of red wilt, annual broadleaf weed and firefly were sown, and tubers of Mizugayatsuri and Urikawa were planted. Was planted three times, and flooded to 3 cm.

For the treatment of the drug, a predetermined amount of the granule produced according to Formulation Example 1 described below was hand-sprayed on the water surface 7 days after the rice transplantation. Management and nurturing are performed in a greenhouse, and chemical treatment 3
After a week, the herbicidal effect and the phytotoxicity of rice were observed and investigated. Table 1 shows the results. The drug used in this test example was a compound represented by the aforementioned formula (9) and 1- (2-
Chloroimidazo [1,2- a ] pyridin-3-ylsulfonyl) -3- (4,6-dimethoxy-2-pyrimidinyl) urea [referred to as “Compound A” in Table 1]. The numerical values in the table indicate the herbicidal effect and the phytotoxicity to rice, and are specifically as follows.

[0031]

Further, the numerical value in parentheses in Table 1 indicates Colb
Expression of y

(Equation 1)

It is the expected value (E) of the weed suppression value of the herbicidal composition of the present invention calculated by (Colby, S. et al.).
R. , WEEDS 15, 20-22, 1967). In the formula, α and β are weed suppression values when the dose of each component present in the herbicidal composition is applied as a single agent.

[0034]

[Table 1]

Formulation Example 1 Granules Compound of Formula (9) 1 part by weight 1- (2-chloroimidazo [1,2- a ] pyridin-3-ylsulfonyl) -3- (4,6-dimethoxy-2- Pyrimidinyl) urea 0.3 parts by weight Sodium ligninsulfonate 2 parts by weight Bentonite 30 parts by weight Talc 66.7 parts by weight These components are thoroughly mixed until uniform, and granulated by a conventional method to obtain granules.

Formulation Example 2 Water-dispersible compound of the formula (9) 30 parts by weight 1- (2-chloroimidazo [1,2- a ] pyridin-3-ylsulfonyl) -3- (4,6-dimethosin-2) -Pyridinyl) urea 6 parts by weight Sodium alkyl sulfate 2.5 parts by weight Polyoxyethylene alkyl phenyl ether 2.5 parts by weight Clay 59 parts by weight These components are thoroughly mixed until uniform, finely pulverized, and water-treated by a conventional method. It should be a sum.

Formulation Example 3 Emulsion Compound of formula (9) 20 parts by weight 1- (2-chloroimidazo [1,2- a ] pyridin-3-ylsulfonyl) -3- (4,6-dimethoxy-2-pyridinyl) ) Urea 7 parts by weight Polyoxyethylene alkylaryl ether 10 parts by weight Xylol 63 parts by weight These components are mixed well until uniform, dissolved and made into an emulsion by a conventional method.

[0038]

Industrial Applicability The present invention can provide a herbicide having advantages such as a broad herbicidal spectrum, a long-lasting herbicidal effect, and a remarkable herbicidal effect at a low dose.

──────────────────────────────────────────────────続 き Continuation of the front page (56) References JP-A-2-1481 (JP, A) JP-A-3-279368 (JP, A) JP-A-2-67209 (JP, A) JP-A-3- 291203 (JP, A) JP-A-3-173808 (JP, A) JP-A-2-131413 (JP, A) (58) Fields investigated (Int. Cl. ⁷ , DB name) A01N 47/38 A01N 47 / 36 101 REGISTRY (STN) CA (STN)

Claims (1)

(57) [Claims] (1) Formula (1) (Wherein, R ₁ and R ₂ are the same or different and each represents a lower alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, or R ₁ and R ₂ have the same number of carbon atoms as the nitrogen atom to which they are bonded) Represents 4 to 6 azacycloalkanes, wherein A is of the formula (2): Formula (3), Formula (4), Or formula (5): X is a lower alkyl group which may be substituted with a hydrogen atom or a hydroxyl group, or a cycloalkyl group, an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyl group, a phenoxy group, a benzyl group, an α-hydroxy group. A benzyl group, a halogen, a nitro group, an amino group or a trifluoromethyl group, m represents a number of 0, 1, 2 or 3, and n represents a number of 0, 1 or 2.) Formula (6) A herbicide obtained by mixing as an active ingredient 1- (2-chloroimidazo [1,2- a ] pyridin-3-ylsulfonyl) -3- (4,6-dimethoxy-2-pyrimidinyl) urea represented by Composition.