JP3406008B2 - Herbicide composition - Google Patents

Description

Description: BACKGROUND OF THE INVENTION The present invention relates to a compound represented by the formula (1): ## STR1 ## 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 represent a nitrogen atom to which they are bonded. Represents an azacycloalkane having 4 to 6 carbon atoms, and A is represented by the following formula (2): Formula (3): Formula (4) Or formula (5): 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 0, 1 or 2) and a triazole compound represented by the formula (6): 1- (2-chloroimidazo [1,2- a ] pyridin-3-ylsulfonyl) -3-
The present invention relates to a herbicidal composition containing (4,6-dimethoxy-2-pyrimidinyl) urea and 3- (2-phenylisopropyl) -1-paratolyl urea as active ingredients. The compound represented by the formula (1) is disclosed in
No. 1481, and describes that it shows an excellent herbicidal effect against foxtails and the like. 1-
(2-Chloroimidazo [1,2- a ] pyridin-3-ylsulfonyl) -3- (4,6-dimethoxy-2-pyrimidinyl) urea is a compound described in JP-A-64-38091. And is known to be effective against broadleaf and perennial weeds. 3- (2-phenylisopropyl) -1-paratolyl urea is disclosed in
No. 35454, and is known to have a high herbicidal effect on Cyperaceae weeds such as fireflies and sedges. The compound represented by the formula (1) is
Broad-leaved weeds and perennial weeds, which have grown, have a weak herbicidal effect and require a large amount of spraying to achieve a sufficient effect. There are problems such as the possibility of occurrence. 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. Also, 3-
(2-Phenylisopropyl) -1-paratolyl urea has almost no effect on sand millet, broadleaf weeds and urikawa. As described above, various problems have been raised when these compounds are used alone as herbicides. Further, 1- (2-chloroimidazo [1,2
-A ] pyridin-3-ylsulfonyl) -3- (4,6
-Dimethoxy-2-pyrimidinyl) urea and 3- (2
-Phenylisopropyl) -1-paratolyl urea is disclosed in Japanese Patent Application Laid-Open No. 1-207210 for its usefulness. However, the herbicidal composition contains a compound represented by the general formula (1). Nothing is mentioned about the combination. In addition, the herbicidal composition exhibits a high herbicidal effect on most weeds in the early stage of weed development, but it is difficult to completely kill the rice flour, and especially on the growing rice flour. There is a problem that the herbicidal effect is extremely low. [0015] In recent years, the occurrence of perennial weeds, which are the most harmful weeds in paddy fields, such as Tainubie, Spodoptera striata, Firefly and Urikawa, has become 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. . Means for Solving the Problems The inventors of the present invention have made intensive studies to solve the above problems, and as a result, the formula (1)
And 1- (2-chloroimidazo [1,2
-A ] pyridin-3-ylsulfonyl) -3- (4,6
-Dimethoxy-2-pyrimidinyl) urea and 3- (2
Surprisingly, the composition containing (-phenylisopropyl) -1-paratolyl urea as an active ingredient can obtain a broader herbicidal spectrum exceeding the applicable range obtained by the single agent application, and furthermore, the growth has progressed. A high herbicidal effect was also observed on red foxtail. In addition, it does not cause phytotoxicity to rice and shows a remarkable herbicidal effect at a low dose.
In addition, synergistic effects that could not be expected at all, such as long-lasting effects, were recognized, and it was also found that paddy fields of sandy loam showed a phytotoxicity-reducing effect on rice, thereby completing the present invention. 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): Wherein A and n are the same as defined above, and a compound represented by the formula (8): (Wherein Y is a halogen atom, R ₁ and R ₂ are the same as described above), and the compound is optionally oxidized with an appropriate 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) thus produced, preferred specific examples of one of the active ingredients in the present invention include:
Formula (9) The compound shown by these is mentioned. Further, 1- (2-chloroimidazo [1,2- a ] pyridin-3-ylsulfonyl) -3- (4,6 dimethoxy-) used as an active ingredient in the present invention is used.
2-Pyrimidinyl) urea can be produced according to the method disclosed in JP-A-64-38091, and 3- (2-phenylisopropyl) -1-paratolyl urea is described in JP-B-48-35454. It can be manufactured by the method described below. 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 was observed in a wide range of mixing ratio, and 1- (2-) was added to 1 part by weight of the compound represented by the formula (1).
0.01 to 10 parts by weight of chloroimidazo [1,2- a ] pyridin-3-ylsulfonyl) -3- (4,6-dimethoxy-2-pyrimidinyl) urea, 3- (2-phenylisopropyl) -1 -By mixing paratolyl urea in a ratio of 0.1 to 20 parts by weight, the herbicidal composition of the present invention can be produced. The herbicidal composition of the present invention thus produced has a high herbicidal effect obtained by soil treatment before and after germination of weeds, and can be used safely without substantially damaging rice. is there. The herbicidal composition of the present invention may be sprayed with the drug substance itself, but may be mixed with various solid or liquid carriers used in general agricultural chemical 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 solid or 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 auxiliary 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 formulating the composition, the mixing ratio of the herbicidal composition of the present invention is 0.05% by weight of the active ingredient.
The active ingredient can be freely selected within the range of ~ 95%, but preferably the active ingredient is 0.5% ~ 70% and the carrier is 1 ~ 99%.
%, Preferably 40 to 90%, and 0 to 20%, preferably 1 to 7% of an auxiliary agent.
In addition, other herbicides, plant growth regulators, insecticides, fungicides,
A wider range of effects can be expected when used in combination with pesticides such as acaricides and fertilizers. When the herbicidal composition of the present invention is actually used, it is necessary to appropriately select the amount to be used according to the time of use, weather conditions, method of use, type of use, place of use, target weed, target crop, etc. Those skilled in the art are free to make the most of their experience. The dosage of the herbicidal composition of the present invention is generally 5 to 500 g per 10 ares,
Preferably it is 10-300 g. The present invention will be specifically described below with reference to Test Examples and Preparation Examples. The drug used in the following test examples and preparation examples was a compound represented by the formula (9), 1-
(2-chloroimidazo [1,2- a ] pyridin-3-ylsulfonyl) -3- (4,6-dimethoxy-2-pyrimidinyl) urea [hereinafter referred to as “compound A”] and 3-
It is a composition comprising (2-phenylisopropyl) -1-paratolyl urea [hereinafter referred to as “compound B”]. The numerical values in the table showing the results of the following test examples show the herbicidal effect and the phytotoxicity on rice, and are specifically as follows. Numerical value Herbicidal effect Crop damage degree 5 Herbicidal rate 90% or more (almost dead) Serious 4 Herbicidal rate 70-89% Major harmful 3 Herbicidal rate 40-69% Medium harmful 2 Herbicidal rate 20-39% Less harmful 1 Weed control rate 6 to 19% Slightly harmless 0 Weed control rate 5% or less (almost no effect) No harm Test example 1 Paddy soil was filled into a 1/5000 arel Wagner pot, water was added, and water was removed. The seeds of T. brasiliensis, annual broadleaf weeds and fireflies were sown, tubers of Sphagnum foliage and Urikawa were planted and flooded to 3 cm. In the treatment of the drug, a predetermined amount of a granule produced according to Preparation Example 1 described later was hand-sprayed on the water surface 11 days after sowing of the weed. Management and rearing were performed in a greenhouse, and the herbicidal effect was observed and investigated three weeks after the chemical treatment. The drugs used in this test example were a compound of formula (9) alone, a composition of compound A + compound B, a compound of formula (9) + composition of compound A + compound B, and a compound of formula (9) + Compound B. The test results are shown in Table 1. [Table 1] Test Example 2 A 1/5000 are Wagner pot was filled with paddy soil (sand loam) having a large water leakage, and water was added to remove water.
The rice at the leaf stage was transplanted and submerged to 5 cm. Drug treatment
Two days after rice transplantation, a predetermined amount of a wettable powder manufactured according to Preparation Example 2 described below was diluted with 5 ml of water and dropped into a pot. For 2 days from the day after the chemical treatment, an amount of water corresponding to a water depth of 3 cm was leaked from the lower part of the pot. Thereafter, the water depth was kept at 3-4 cm. Management and rearing were performed in a greenhouse, and 30 days after the chemical treatment, the above-ground living weight of rice was measured, and the ratio to the untreated area was determined. Table 2 shows the results. The drugs used in this test example are the compound of formula (9) alone, a composition of compound A + compound B, and a composition of compound of formula (9) + compound A + compound B. [Table 2] Test Example 3 A paddy field was divided into 20 m ² in each section, and rice plants at the two leaf stage were planted shallowly (transplant depth: 1 cm). Weeds were sown with seeds of red croaker, annual broadleaf weeds (Azena, Kikasigusa) and fireflies, and mixed with tubers of Sphagnum foliage and Urikawa. A predetermined amount of a wettable powder prepared in accordance with Formulation Example 2 described below was diluted with water to prepare a drug. Using this drug, rice was transplanted 3 days after transplantation and 14 days after transplantation using Jolo. The entire surface was uniformly flooded. Water depth during the test period is 3-5
cm. The investigation was performed by observation 30 days after drug treatment. The results are shown in Tables 3 and 4. The drugs used in this test are the same as in Test Example 1. [Table 3] [Table 4] Formulation Example 1 Granules Compound of Formula (9) 1 part by weight Compound A 0.2 part by weight Compound B 2 parts by weight Sodium ligninsulfonate 2 parts by weight Bentonite 20 parts by weight Talc 74.8 parts by weight Mix well until uniform and granulate by conventional methods to make granules. Formulation Example 2 wettable powder 10 parts by weight of compound of formula (9) Compound A 3 parts by weight Compound B 30 parts by weight Sodium alkyl sulfate 2.5 parts by weight Polyoxyethylene alkyl phenyl ether 2.5 parts by weight Clay 52 parts by weight These components are thoroughly mixed until uniform, finely pulverized and made into a wettable powder by a conventional method. Formulation Example 3 Emulsion 10 parts by weight of compound of formula (9) Compound A 5 parts by weight Compound B 20 parts by weight Polyoxyethylene alkylaryl ether 10 parts by weight Xylol 55 parts by weight These components are mixed well until uniform. And dissolved to form an emulsion by a conventional method. Industrial Applicability The present invention has a wide range of herbicidal spectrum against rice blast, which is a strong harmful plant in paddy fields, broadleaf weeds and perennial weeds, and has phytotoxicity against rice under extremely bad conditions such as sandy loam. And a herbicide in which the herbicide is significantly reduced.

────────────────────────────────────────────────── ─── Continuation of front page (56) References JP-A-2-1481 (JP, A) JP-A-3-279368 (JP, A) JP-A-1-207210 (JP, A) (58) Field (Int.Cl. ⁷ , DB name) A01N 47/38 A01N 47/30 A01N 47/36 101 CA (STN) REGISTRY (STN)

Claims (1)

(57) [Claims] [Claim 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 represent the number of carbon atoms together with 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) 1- (2-chloroimidazo [1,2- a ] pyridin-3-ylsulfonyl) -3- (4,6-dimethoxy-2-pyrimidinyl) urea and 3- (2-phenylisopropyl) -1 -A herbicidal composition containing paratolyl urea as an active ingredient.