JPS63258467A - 2-phenoxytriazine derivative and herbicide - Google Patents

Abstract

NEW MATERIAL:A 2-phenoxytriazine derivative expressed by formula I [X is H or halogen; R<1> is formyl, COOR<3> (R<3> is H, lower alkyl or benzyl); R<2> is methyl or methoxy]. EXAMPLE:Methyl 2-(4,6-dimethoxy-s-triazin-2-yl)oxybenzoate. USE:A herbicide which is a 2-phenoxytriazine based compound having substituent groups introduced into specific positions on the triazine and benzene rings. PREPARATION:For example, a compound expressed by formula II is reacted with a triazine compound expressed by formula III (R<4> is halogen) in the presence of a base, preferably in a solvent within the temperature range of room temperature - the boiling point of the solvent for 1-24hr to afford the aimed compound expressed by formula I.

Description

Detailed Description of the Invention (Field of Industrial Application) The present invention relates to a novel 2-phenoxytriazine derivative and a herbicide containing the same as an active ingredient that can be applied to paddy fields, fields, non-agricultural land, etc. .

(Conventional technology) Chemical abstract (Chem, abst,
) Vol. 87, 68298 describes that 2-phenoxytriazine derivatives having a carboxyl group on the benzene ring have bactericidal activity. Also, JP-A-54-5
5729 describes that 2-phenoxypyrimidine derivatives having a carboxyl group on the benzene ring have herbicidal activity.

(Problems to be Solved by the Invention) However, the above-mentioned chemical abstract does not mention anything about herbicidal activity.

Furthermore, the compounds described in the above-mentioned publications have the disadvantage that their herbicidal activity is insufficient.

As a result of intensive research aimed at developing compounds with excellent herbicidal activity regarding 2-phenoxytriazine compounds, the present inventors have discovered that the compounds of the present invention have substituents introduced into specific positions of the triazine ring and the benzene ring. They discovered that it exhibits excellent herbicidal effects and completed the present invention.

(Means for Solving the Problems) The 2-phenoxytriazine derivative of the present invention has the general formula [wherein, X represents a hydrogen atom or a halogen atom, and R1
is a formyl group or a group C02R'', (wherein R3 represents a hydrogen atom, a lower alkyl group, or a benzyl group.)
and R2 represents a methyl group or a methoxy group. ]
The compounds of the present invention represented by formula (I) are exemplified in Table 1.

In addition, the compound number will be referred to in the following description.

The compounds of the present invention can be produced according to the following methods, but are not limited to these methods.

[1] [2] [3] (
In the formula, R4 represents a halogen atom, and R1, R2 and X have the same meanings as above. It can be produced by reacting a triazine compound with a triazine compound in the presence of a base, preferably in a solvent at a temperature ranging from room temperature to the boiling point of the solvent for 1 to 24 hours. When the reaction is carried out without a solvent, an alkali metal carbonate such as anhydrous potassium carbonate may be used as a base and the reaction may be carried out within a temperature range of 120 to 160°C.

Examples of the solvent used here include hydrocarbon solvents such as benzene, toluene, and xylene, methylene chloride,
Halogenated hydrocarbon solvents such as chloroform, ethyl ether, isopropyl ether, tetrahydrofuran,
1. Ether solvents such as 4-dioxane, acetone,
Ketone solvents such as methyl ethyl ketone, ester solvents such as methyl acetate and ethyl acetate, dimethylformamide,
Examples include aprotic polar solvents such as dimethylacetamide and dimethylsulfoxide, acetonitrile, and water. Bases include alkali metals such as sodium metal and potassium metal, alkali metal hydrides and alkaline earth metal hydrides such as sodium hydride, potassium hydride, and calcium hydride, sodium carbonate, potassium carbonate, and hydrogen carbonate. Examples include carbonates such as sodium and potassium hydrogen carbonate, and metal hydroxides such as sodium hydroxide and potassium hydroxide.

(Method B) Among the compounds of the present invention, the compound represented by formula [5] (wherein, It can be produced by reacting in a polar solvent, water, or a mixed solvent of a polar solvent and water for 0.5 to 24 hours under cooling with water or at a temperature within the boiling point of the solvent.

Examples of the solvent used here include acetone, t-
Examples include polar solvents such as butyl alcohol, acetic acid, pyridine, and dioxane, and mixed solvents of water and polar solvents such as acetone, t-butyl alcohol, acetic acid, pyridine, and dioxane. Oxidizing agents include oxygen, hydrogen peroxide, chromic acid, silver oxide, potassium permanganate, barium permanganate, calcium permanganate,
Examples include permanganates such as magnesium permanganate.

Next, an example will be given and explained.

Example 1 Synthesis of methyl 2-(4,6-dimethoxy-S-triazin-2-yl)oxybenzoate (Compound 1) 2-chloro-4,6-simethoxy-5-t-riazine (3,2 g)
and potassium carbonate (3.2 g) were suspended in dimethylformamide (20 ml), then methyl salicylate (3.5 g)
A solution prepared by dissolving the above in dimethylformamide (10 ml) was added dropwise at room temperature. The reaction was completed by heating and stirring at 70 to 80° C. for 3 hours, and after cooling, the reaction solution was poured into water, and the precipitated crystals were filtered. The crystals were recrystallized from methanol to obtain the title compound as white crystals (5.4 g).

(Melting point 64-68°C) Example 2 Synthesis of 2-chloro-6-(4,6-simethoxyS-)riazin-2-yl)oxybenzoic acid (Compound 10) 2-chloro-6-(4,6 -dimethoxy-S-triazin-2-yl)oxybenzaldehyde (4° Og)
was dissolved in acetone (30 ml), and an equimolar amount of potassium permanganate aqueous solution (20 ml) was added dropwise little by little.

After stirring at room temperature for 4 hours, the deposited precipitate was filtered. The furnace solution was made acidic with a 5% aqueous hydrochloric acid solution, and extracted with salting out with ether. After washing the extract with water and drying, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to obtain the title compound (1.6 g).

(Melting point: 138-140°C) The herbicide of the present invention contains a 2-phenoxytriazine derivative, which is the compound of the present invention.

When using the compound of the present invention as a herbicide, it can be used alone or in combination with carriers, surfactants, dispersants, adjuvants, etc. that are commonly used in the formulation of agricultural chemicals, such as hydrating powders, granules, etc. It can be formulated and used in various forms such as a tablet, emulsion, or powder.

Examples of carriers used in formulation include di-
Clyte, talc, bentonite, clay, kaolin,
Examples include solid carriers such as diatomaceous earth, white carbon, vermiculite, slaked lime, silica sand, ammonium sulfate, and urea, and liquid carriers such as isopropyl alcohol, xylene, cyclohexane, and methylnaphthalene. Examples of surfactants and dispersants include alcohol sulfate ester salt, alkylaryl sulfonate, lignin sulfonate, polyoxyethylene glycol ether, polyoxyethylene alkylaryl ether, polyoxyethylene sorbitan monoalkylate, etc. can be mentioned. Examples of the adjuvant include carboxymethylcellulose, polyethylene glycol, gum arabic, and the like. When used, it can be diluted to an appropriate concentration and sprayed, or applied directly.

Moreover, the herbicide of the present invention can also be used in combination with other herbicides.

The herbicide of the present invention can control various weeds that occur in rice fields by treating the soil with water or treating the foliage before or after the germination of the weeds. In addition, various weeds occurring in the fields can be controlled by treating the soil or treating the foliage before or after the germination of the weeds.

The herbicide of the present invention has an active ingredient of 0.1g per 10 ares.
Apply ~1 kg. In addition, when spraying on plant stems and leaves, ip
Apply diluted to 110,000 ppm.

Next, Examples of the herbicide of the present invention will be given, but the present invention is not limited to this range.

Incidentally, the percentages described in the examples indicate weight percentages.

Example 3 (hydrating powder) Compound (1) 10%, Emulgen 810 (registered trademark of Kao Soap Co., Ltd.) 0.5%, Demol N (registered trademark of Kao Soap Co., Ltd.) 0.5%, Kunilite (Kunimine Kogyo Co., Ltd.) A wettable powder was prepared by uniformly mixing and pulverizing 201.20% of Zikrite (registered trademark of the company) and 69% of Zikrite (registered trademark of the company).

Example 4 (Emulsion) 30% of Compound <3), 20% of cyclohexanone, 11% of polyoxyethylene alkylaryl ether, 4% of calcium alkylbenzene sulfonate, and 35% of methylnaphthalene were uniformly dissolved to prepare an emulsion.

Example 5 (powder) Compound (6) 5%, lauryl alcohol sulfate sulfur salt 2%, sodium lignin sulfonate 5%
%, carboxymethyl cellulose 2%, and clay 86
% is evenly mixed and ground. Add 20 parts by weight of water to 100 parts by weight of this mixture, knead it, and use an extrusion type granulator for 14 parts by weight.
After processing into granules of ~32 meshes, they were dried to form granules.

Example 6 (Powder) 2% of compound (7), 5% of diatomaceous earth, and 93% of clay were uniformly mixed and ground to obtain a powder.

(Effects of the Invention) The compounds and herbicides of the present invention can effectively control annual weeds that occur in rice fields, such as Japanese grasshopper, Japanese cypress, Japanese cypress, Japanese cypress, Japanese cypress, and perennial weeds such as Japanese cypress, Japanese cypress, and black cypress. Also,
Barnyard grass, crabgrass, blackberry, foxtail grass, sycamore, sycamore, oat, Italian ryegrass, Japanese knotweed, blueberry, whiteweed, pigweed, crocodile, golden deer, stagweed, chickweed, morning glory, Japanese fir, staghorn snail, Japanese snail, and itch. It is also possible to effectively control annual weeds such as Japanese grass, Japanese grass, buckwheat, Japanese grass, and American melium, as well as perennial weeds such as common grass, johnson grass, Japanese grass, and grasshopper. On the other hand, the compound of the present invention is highly safe for crops, and furthermore, the compound of the present invention has an excellent herbicidal effect compared to the known compounds described in the above-mentioned publications.

Next, the effects of the herbicide of the present invention will be explained using test examples.

Test Example 1 (Stem and Leaves Treatment) Seeds of Japanese barnyard grass, Japanese knotweed, Japanese knotweed, Japanese violet, white cabbage, and Japanese cypress were sown in a 100 crrr bottle filled with soil, and covered with soil to an area of 0.5 to 100 ml. The pot was grown in a glass room at 20-25°C for 2 weeks and then used in Example 3.
4 per 10 ares with the active ingredient of a hydrating agent prepared according to
The solution was diluted with 100 J2 of water per 10 are to give a total weight of 0.00 g and sprayed on the surfaces of the leaves. The investigation was conducted on the 14th day after drug treatment according to the criteria in Table 2. The results are shown in Table 3 as an index.

Table 2 Table 3 (Notes) 1. The abbreviations for test plants represent the following plants. (The same applies to other tables.) Ech; Barnyard millet (Echinochloa
crus-gali) Dig;
Polygonum nodosum
) Ama; Aobiyu (Aaaranthus)
retroflexus) Che; Shiroza (
Chenopodium album) Cyi; Cyperus 1ria 2, comparative compounds A, B and C represent the following compounds (the same applies to other tables) (Described in JP-A-54-55729) Test Example 2 (Soil treatment) Seeds of Japanese barnyard grass, Japanese knotweed, Japanese knotweed, Japanese violet, white-tailed grass, and Japanese cypress were sown in a 100Crrf pot filled with soil, and covered with soil to an area of 0.5 to 100 ml. The day after sowing, water prepared according to Example 3 was added. Japanese medicine with 10 active ingredients
100 rho per 10 are so that it is 400g per are
of water and sprayed on the soil surface. The results of the investigation conducted on the 20th day of drug treatment according to the criteria in Table 2 are shown in Table 4 as an index.

Table 4

Claims (2)

[Claims] (1) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, X represents a hydrogen atom or a halogen atom, and R^
1 is a formyl group or a group CO_2R^3, (in the formula, R^
3 represents a hydrogen atom, a lower alkyl group, or a benzyl group. ), and R^2 represents a methyl group or a methoxy group. ] A 2-phenoxytriazine derivative represented by. (2) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, X represents a hydrogen atom or a halogen atom, and R^
1 is a formyl group or a group CO_2R^3, (in the formula, R^
3 represents a hydrogen atom, a lower alkyl group, or a benzyl group. ), and R^2 represents a methyl group or a methoxy group. ] A herbicide containing a 2-phenoxytriazine derivative represented by the following as an active ingredient.