JPS58113156A - Phenoxyalkanoic acid benzylamide derivative and herbicide - Google Patents

Abstract

NEW MATERIAL:A compound of formulaI(X is lower alkoxy, halogen, cyano, nitro, propionyl; Y is H, lower alkyl; R is lower alkyl; Z is H, lower alkyl, lower alkoxy, nitro; where when Z is H, lower alkyl, lower alkoxy and X is halogen, the halogen of X is other than chlorine). EXAMPLE:N-Benzyl-2-(3-methoxyphenoxy)-butylamide of formula II. USE:Selective herbicide: it scarcely causes chemical injury by auxin and is completely free from toxicity to men, animals, fishes and shells and from strange odor. PREPARATION:For example, the reaction of a compound of formula III (A is chlorine, bromine) such as 2-(3-methoxyphenyl)-butyroyl chloride with another one of formula IV such as benzylamine is carried out in a solvent such as toluene in the presence of a weak alkali such as pyridine at 0-30 deg.C.

Description

[Detailed description of the invention] This invention is based on the general formula (In the formula, X is a 1-family alkoxy group or a halogen atom.

Indicates a cyano group, nitro group, or propionyl group.

Y represents a hydrogen atom or a lower alkyl group, and Z represents (2) a hydrogen atom, a lower alkyl group, a lower alkoxy group, or a nitro group. However, when Z is a hydrogen atom, a lower alkyl group, or a lower alkoxy group, and χ is a halogen atom, the halogen atom of χ represents a halogen atom other than a chlorine atom. ), and a herbicide containing this novel benzylamide derivative of phenoxyalkanoic acid as an active ingredient.

Herbicides contain phenoxy compounds as active ingredients.

Many proposals have been made since ancient times, and many are commercially available, such as Rei 4. -1) C active ingredient 2.4
-dichlorophenoxyacetic acid), 2.4-D],
) (Active ingredient z -(2,4-dichlorophenoxy)propionic acid:] M c p (Active ingredient 2-methyl-
4-chlorophenoxyacetic acid] or MCPCA [active ingredient 'N-(2-chlorophenyl)-2-methyl-
Herbicides such as 4-chlorophenoquine acetamide are used. These conventional herbicides generally have excellent herbicidal effects against broad-leaved weeds (3) compared to conventional herbicides, but they have an auxin effect on rice crops. They have a common characteristic that they are accompanied by drug-induced harm such as inhibition of tillering and malformations.

The inventors synthesized various compounds of this family and searched for their plant activities with the aim of finding a compound among phenoxy compounds that has excellent herbicidal activity and is free from phytotoxic effects. .

As a result, we succeeded in synthesizing a benzylamide derivative of fenoquine alkanoic acid, which is a new compound represented by the above-mentioned general formula CI) and which has not been described in the literature. This invention was completed based on the discovery that the present invention has the ability to selectively eliminate a wide range of weeds that occur in crops without causing any chemical damage to a single crop.

In other words, the herbicide of the present invention not only has an excellent herbicidal effect on broad-leaved weeds but also on weeds due to its whitening action, and is also effective against conventional rice crops and its related crops, compared to conventional herbicides. Due to the auxin effect seen in (4), there is almost no chemical harm, and there is no toxicity or strange appearance to humans, livestock, fish and shellfish.

The benzylamide derivative of fenoginine alkanoic acid in this invention can be synthesized, for example, by the following reaction.

(However, χ, Y and Z in Formula 1 have the same meanings as above. A means a chlorine atom or a bromine atom.) The above reaction is carried out in the presence of a suitable solvent.

), triethylamine, sodium carbonate, or potassium carbonate.The solvent used in the reaction is an aromatic hydrocarbon such as benzene, toluene, or xylene.

Diethyl ether, tetrahydrofuran, dioxy(5) Ethers such as san and methyl ethyl ketone.

Examples include ketones such as dimethyl ketone. The reaction temperature varies depending on the types of reagents and solvents used, and is not particularly limited, but is usually suitably carried out at 0°C to 30°C.

Reaction time is approximately 1 to 10 hours. Next, specific synthesis examples of the present invention will be given.

Next, an example of its synthesis will be shown.

Synthesis Example I Synthesis of N-benzyl-2-(3-methoxyphenoxy)-butyramide (Compound No. 3 in Table 1 below) Benzylamine 1.7y (0,013 mol) Tohyridine 1. A solution of 0 g (0,013 mol) in 20 m of toluene (mol) in 50 m6 of toluene was added dropwise.

After stirring for 1 hour and standing overnight, the reaction mixture was washed with water, diluted hydrochloric acid, caustic soda, and water in this order. The toluene layer was dehydrated, and the toluene was distilled off. The obtained crude crystals (6) were recrystallized with ethanol to obtain 1.62 kg of colorless needle-like N-benzyl-2-(3-methoxyphenoquine)-butyramide having a melting point of 63 to 0/1°C.

Synthesis Example 2 Iku~benzyru2~(3-nitro7x, /quin)
-Synthesis of butylamide (Compound No. m Co. 2 in Table 1 below) 1.6 y (0,015 mol) of benzylamine and 71.2 g (0,01'5 mol/l/) of topyridine were added to l. Dissolve in x y 30 me and stir at room temperature for 4'1].
-(3-nitrophenoquine)-butyroyl chloride 3
．． :L y (0,0], 33 mol of toluene 30
The warm solution was added dropwise. Then, treatment was carried out according to Synthesis Example 1 (1
The crude crystals obtained were recrystallized from ethanol and showed pale yellow needle-like N-benzyl-2-(3-nitrone h5.) with a melting point of 114-116°C.

, 7noxy)-butyramide was obtained.

Synthesis Example 3 Synthesis of N-(2-methoginebenzyl]~2-(/1-nitrophenoxy)~butyramide ((7) compound of compound number 15 in Table 1 below) 2-methoxybenzylamine 1.9y( o, o14 mol) (!: Pyridine 12 g, (0,015 mol) was dissolved in 50 ml of toluene ψr.1 According to Synthesis Example 1, 2-
(4-nitrophenoxy) ~butyroyl chloride 2.
A solution of 8 g (0,012 mol) in 30 ml of toluene was added dropwise, and the solution was 37+! l,ta. The capped crude crystals were recrystallized with ethanol to give colorless needle-like N-(2-methoxybenzyl)-2-(4-
21.lofenoquine)-butyramide 2.4F was obtained.

It was manufactured according to the above synthesis example. Examples of the novel benzylamide derivatives of phenoxyalkanoic acid in this invention are as follows:
Table 1 lists 12.

In addition, the upper row of elemental analysis values in Table 1 shows theoretical values, and the lower row shows actual measured values.

(8) Table 1 (9) Continuation of Table 1 (10) Continuation of Table 1 Continuation of Table 1 In this invention. Benzylamide derivatives of enoxyalkanoic acids are used as herbicides.In the first case, in accordance with the customary practice of pesticide formulations, the inert solid, j-Q form.

One-stop agent using liquid phase and emulsifying dispersant.

It can be used in any dosage form such as powder, emulsion, aquarium tablets, aerosol, smoke, etc. These inert phases include, for example, talc, clay, kaolin, diatomite, and calcium carbonate.

Potassium chlorate, saltpeter, wood flour, nitrocellulose.

Starch, benzene, xylene, n-hexane.

Examples include gum arabic, vinyl chloride, carbon dioxide, Freon, propane, and butane.

Further, auxiliary agents 1 for formulation, such as spreading agents, diluents, surfactants, solvents, etc., may be appropriately incorporated.

Also fungicides, insecticides and other pesticides, urea.

Ammonium sulfate, ammonium phosphorus, potassium salts and their fertilizing substances.

Can be used by appropriately mixing with soil improvement agents, etc.
Ru・′. The amount of herbicide used in this invention varies depending on the method of use, place of use, type of target weed, etc., but the amount of the active ingredient, that is, the amide derivative of Phenogear (co3) alkanoic acid, is 0.5 to 1 per are.
007. It is preferable to use 1 to 50 y.

Next, examples of the herbicide of this invention will be given. Note that each part in each example represents 1 part by weight.

Examples] 50 parts of N-hensyl-2-(3-methoxyphenoxy)-butyramide (compound No. 3).

40 parts of xylene, Tsurupol 800 (surfactant).

(trade name) were mixed and dissolved to obtain an emulsion.

Example 2 50 parts of N-benzyl-2-(3-nitronenoxy)-butyramide (compound No. 12), kaolin 3
0 parts of bentonite, 15 parts of sodium lignin sulfonate, and 5 parts of sodium ligninsulfonate were mixed and ground to produce an irrigation agent N-benzyl-2-(4-methyl-3-nitrophenoxy]-butylamide 7 parts (compound No. 8) and bentonite. ) 60 parts, talc 3
o part.

(14) After mixing and pulverizing 3 parts of sodium naphthalene sulfonate, add an appropriate amount of water, knead, and granulate using a granulator.
Granules were obtained.

Next, the effects of the herbicide of the present invention will be specifically explained using experimental examples. In addition, the test compound number in each experimental example is the same as the compound number in Table 1.

Experimental example] Soil treatment test 1 Paddy soil (Hongbai soil selection) in a bot of /9000 are
Seeds of various weeds such as wild grass, broad-leaved weeds (Japanese grass, azalea, and Japanese cypress), bulrushes, and cypress were uniformly mixed and sown on the surface layer.

Paddy rice seedlings at the 18- to 2-leaf stage were transplanted and water was added to create a flooded state of 2α. Next, after 3 days, each yuzu 1. Each wettable powder produced according to Example 2 was tested during the grass growth period. The results are shown in Table 2.

5: Complete withering 4: Ancient 3: rlI damage 2: Kokichi]: Slight damage O: Harmless (normal growth) In addition, the upper row of each column in Table 2 indicates the amount of active ingredient 509
/R, The lower row shows the results of an experiment conducted at 25g/R.

Table 2 Experimental Example 2 Stalk and Leaf Spraying Test 1/15500 After filling Earl's pot with field soil (diluvial soil), 1 wheat, edible barnyard grass, and black grass were added.

Aobiyu returned home. When each plant had grown to 2 to 3 leaves, 0, 50 w of each irrigation agent produced according to Example 2 was applied.
t% and 0.25wt% aqueous solutions were sprayed using a pressurized + l'i atomizer.

Two weeks after the treatment, the herbicidal effects of each test compound were investigated. The results are shown in Table 3.

The criteria for the herbicidal effect in Table 3 are the same as those for experimental soil stripping.

The upper row of each column in Table 3 indicates the active ingredient concentration of 0.
The results of an experiment were conducted at 50 wt% and the lower row shows 0.25 wt%.

Table 3 (17) From the above experimental results, it was found that the herbicide of this invention is safe for one crop and has excellent herbicidal effects against various weeds. It is recognized as a selective herbicide.

Patent Applicant Ube Industries Co., Ltd. (,1,8) Letter of Amendment July-2, 1980 Commissioner of the Japan Patent Office 1 Indication of Case Patent Application No. 1982-209946 2 Name of Invention Benzylamide of Phenoxyalkanoic Acid Derivatives and herbicides Relationship with the case of the person making the amendment Patent applicant postal code 755 1-12-32 Nishihonmachi, Ube City, Yamaguchi Prefecture (020)
Ube Industries Co., Ltd. Telephone: 03 (581) 331i 4 Amendment order with [-1 attached (voluntary amendment)]

5 Number of inventions increased by amendment None 6 Detailed description of the invention and scope of claims in the specification to be amended.

7 Contents of amendment (1) II! IJ small size) Page 2, last line, the statement [represents a lower alkyl group, Z represents a lower alkyl group] is corrected to ``represents a lower alkyl group, R represents a lower alkyl group, Z represents''.

(2) Page 5 of the specification, 9th line from the bottom, “X in the formula.

The description of "Y"; and "2" is changed to "X, Y, R
and 2”.

(3) The scope of claims is as shown in the attached sheet.

8 Supporting documents (1) Attachment stating the amended scope of claims of Japanese Patent Application No. 56-209946 (1) Attachment Attached scope of amended claims of Japanese Patent Application No. 56-209946 [(1) General formula (wherein X is a lower alkoxy group or a halogen atom.

Indicates an ano group, a dil group, or a propionyl group.

Y represents a hydrogen atom or a lower alkyl group, R represents a lower alkyl group, and 2 represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, or a nitro group.

However, when 2 is a hydrogen atom, a lower alkyl group, or a lower alkoxy group, and X is a halogen atom.

The halogen atom of X represents a halogen atom other than a chlorine atom. ) A benzylamide derivative of phenoxyalkanoic acid.

(2) General formula %formula% (In the formula, X is a lower alkoxy group, a halogen atom.

Indicates a cyan group, nitro group or propionyl group.

Y represents a hydrogen atom or a lower alkyl group, R represents a lower alkyl group, and 2 represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, or a nitro group.

However, when 2 is a hydrogen atom, a lower alkyl group, or a lower alkoxy group, and X is a halogen atom.

The...rogen atom of X indicates a...rogen atom other than a chlorine atom. ) A herbicide characterized by containing a benzylamide derivative of phenoxyalkanoic acid as an active ingredient. "that's all

Claims (1)

[Claims] (1) General formula (wherein X is a lower alkoxy group, a halogen group, a cyano group, a nitro group, or a propionyl group; ZJj: represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, or a nitro group.However, when Z is a hydrogen atom, a lower alkyl group, or a lower alkoxy group, and X is a 710 gen atom, The atom indicates a rogen atom other than the first prince of chlorine. ) A benzylamide derivative of phenoxyalkanoic acid. (2) General formula (1) (Formula [1: ly represents a lower alkoxy group, a halogen atom, a cyan group, a nitro group, or a propionyl group. Y represents a hydrogen atom and a lower alkyl group;
゛Represents a hydrogen atom, lower argyl group, lower alkoxy group, or nitro group. However, when Z is a hydrogen atom, a lower alkyl group, or a lower alkoxy group, and X is a \ halogen atom, the halogen atom in (■) represents a halogen atom other than a chlorine atom. ) A herbicide characterized by containing a benzylamide derivative of phenoxyalkanoic acid as an active ingredient.