JPS585161B2 - All the best - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a herbicidal composition, and more particularly to a herbicidal composition having the formula [wherein,
X is halogen; R1 and R2 are independently hydrogen atoms or lower alkyl groups; Zl and Z2 are independently oxygen or sulfur atoms; R38 and R4 are independently hydrogen atoms or lower alkyl groups; and m is 1 or 2 The present invention relates to a herbicidal composition containing an anilide compound represented by:

The compound of this invention has the formula: (wherein R1+ R2, R3, R4+ Zl + Z2 and m are as defined above.

) compound with formula: (In the formula, X is as defined above.

) can be produced by reacting with α-haloalkanoyl chloride.

This reaction consists of combining a compound of formula (1) with a compound of formula (1) in an inert organic medium (e.g. dioxane) in the presence of an acid acceptor (e.g. an alkali metal carbonate or bicarbonate) from about -10° to
This can be done by mixing at a temperature of 25°C and stirring for about 15 to 120 minutes.

After stirring, the reaction mixture can be washed with water to remove inorganic salts and the solvent can be removed to obtain the desired product.

This product can be used as is or can be further purified by recrystallization or other conventional methods.

The compound of formula ■ has the formula: (In the formula, R and R2 are as defined above.

) Substituted aniline of the formula: (In the formula, Hal is a halogen atom such as a chlorine atom or a bromine atom, and Z1 Z2+ R3, R4 and m are as described above.

) can be produced by reacting with a compound.

This reaction involves combining a compound of formula (1) with a compound of formula (2) in an inert organic medium (e.g. dimethylformamide) and a co-acceptor (
For example, by mixing in the presence of an alkali metal carbonate or bicarbonate) and heating at reflux for about 4 to 48 hours.

After heating, the reaction mixture is filtered and distilled to obtain the desired product.

Compounds of formula V have the formula: (In the formula, n is as defined above.

) is the acetal of the formula: (wherein Z1.Z2.R3, R4 and m are as defined above.

) can be produced by reacting with a diol or dithiol.

In this reaction, the compound of formula (1) and the compound of formula (2) are mixed in approximately equimolar amounts under anhydrous conditions in the presence of an acid catalyst (e.g., sulfuric acid or toluenesulfonic acid), and the resulting mixture is about 1 to 4
This can be carried out by heating under reflux for a period of time.

After heating, the reaction mixture can be distilled under reduced pressure to obtain the desired product.

Example 1 (1) Preparation of 2-chloromethyl-1,3-dioxolane Into a glass flask equipped with a mechanical stirrer, a thermometer and a reflux condenser was added 2-chloroacetaldehyde dimethylacecool (125 g, 1.0 mol). ) and ethanediol-1,2 (62 g, 1.0 mol) were added.

Toluenesulfonic acid (0.3 g) was added to the flask and the reaction mixture was refluxed for about 2 hours.

After refluxing, the reaction mixture was distilled under reduced pressure to remove methanol to obtain the desired product, 2-chloromethyl-1,3-dioxolane.

(2) Production of N-(1,3-dioxolan-2-ylmethytrily-2,6-dimethylaniline) 2,6-dimethylaniline was placed in a glass reaction vessel equipped with a mechanical stirrer, a thermometer 2, and a reflux condenser. (75g),
2-chloromethyl-1,3-dioxolane (25g),
Potassium carbonate (34g) and dimethylformamide (
50 mg) was added.

The reaction mixture was heated to reflux for approximately 18 hours. After heating, the mixture was filtered and distilled to obtain the desired product, N-(1,3-dioxolan-2-ylmethyl)-2,6-dimethylaniline.

(3) Production of N-α-chloroacetyl-N-(1,3-dioxolan-2-ylmethyl)-2,,6-dimethylaniline In a glass reaction vessel equipped with a mechanical stirrer and a thermometer, N
-(1,3-dioxolan-2-ylmethyl)-2,6
-dimethylaniline (7.8 g), sodium bicarbonate (
7,0 g), dioxane (20 ml) and water (4 ml)
) was added.

The mixture was cooled to about 0° C. and chloroacetyl chloride (50 g) was added under stirring over about 15 minutes.

After the addition was complete, stirring was continued for approximately 0.5 hour.

After stirring was completed, ether (100ml) was added and the resulting solution was washed with water.

It is then dried over anhydrous magnesium sulfate, then the solvent is removed and the solid residue is recrystallized from an ether/pentane mixture to yield the desired product, N-α-chloroacetyl-N-, with a melting point of 58-60°C. (1,3-dioxolan-2-ylmethyl)-2,6-dimethylaniline (compound A) was obtained.

Example 2 (1) Preparation of N-(1,3-dioxolan-2-ylmethyl)-2,6-';' Ethylaniline In a glass reaction vessel equipped with a mechanical stirrer, a thermometer and a reflux condenser, 2. ,6-dinitylaniline (75g, 0
．． 5 mol), 2-chloromethyl-1,3-dioxolane (25 g, 0.2 mol), potassium carbonate (22 g, 0.2 mol).
2 mol) and dimethylformamide (50 ml).

The reaction mixture was heated with stirring for approximately 18 hours.

After heating, the reaction mixture was filtered and then distilled to obtain the desired product, N-(1,3-dioxolan-2-ylmethyl)-2,6-ethylaniline.

(2) Production of N-α-chloroacetyl-N-(1,3-dioxolan-2-ylmethyl)-2,6-dinitylaniline N- (1,3-dioxolan-2-ylmethyl)-2,
6-Dinitylaniline (7,7 g) Sodium bicarbonate (
6.0 g), dioxane (20 ml) and water (4 ml)
) was added.

The mixture was cooled to about 0°C and, under stirring, heated to about 15°C.
Chloracetyl chloride (4.0 g) was added over a period of minutes.

Stirring was continued for about 0.5 hours after the addition was complete. After stirring,
Ether (100m) was added to the mixture and the resulting solution was washed with water.

It was then dried over anhydrous magnesium sulfate and the solvent was removed to obtain a solid residue.

This residue was recrystallized from an ether/pentane mixture,
The desired product, N-α, has a melting point of 86° to 87°C.
-Chloroacetyl-N-(1,3-dioxolane-2-
ylmethyl)-2,6-dinitylaniline (compound B)
I got it.

The following compounds were prepared in a similar manner.

Example 3 Dimethyl acetal of 2-chloroacetaldehyde + butanediol-1,2+ 2,6-dimethylaniline +
Chloracetyl chloride-N-(4,5-dimethyl-1
, 3-dioxolan-2-ylmethyl)-α-chloroacetanilide (m, p, 98-101°C, compound C) Example 4 Dimethyl acetal of 2-chloroacetaldehyde + mercaptoethanol + 2,6-dimethylaniline + chloroacetyl Chloride=N-(1,3-oxathiolane-
2-ylmethyl)-2,6-dimethyl-α-chloroacetanilide (m, p, 85-87°C, compound D) Example 5 Dimethyl acetal of 2-chloroacetaldehyde + butanediol-1,3 + 2.6-dimethyl Aniline + chloroacetyl chloride = N-(4-methyl-1,3-dioxan-2-ylmethyl)-2゜6-dimethyl-α-
Chloracetanilide (m.

p, 82-84°C, Compound E) Example 6 Dimethyl acetal of 2-chloroacetaldehyde + propanediol-1,3 + 2-methyl-6-nitylaniline + chloroacetyl chloride = N-chloroacetyl-
N-(1,3-dioxolan-2-ylmethyl)-2-
Methyl-6-Nitylaniline (Oil, Compound F) For practical use as a herbicide, the compound of this invention is generally blended with an inert carrier in a herbicidally effective amount to form a herbicidal composition.

Such herbicidal compositions (which can also be referred to as formulations) make it possible to conveniently apply the active compounds in any desired amount to weed breeding sites.

These compositions may be solids such as dusts, granules, wettable powders, or liquids such as solutions, aerosols, emulsifiable concentrates.

For example, powders can be prepared by grinding and mixing the active compound with a solid inert carrier such as talc, clay, silica, pyrophyllite, or the like.

Granular formulations usually contain a compound dissolved in a suitable solvent.
It can be produced by impregnation onto and into a granular carrier such as atta-pulgites or vermiculates, which usually have a particle size range of about 0.3 to 1.5 mm.

Wettable powders which can be dispersed in water or oil to achieve the desired active compound concentration can be prepared by including a wetting agent in the concentrated powder composition.

In some cases, the active compounds are sufficiently soluble in common organic solvents such as kerosene or xylene that they can be used directly as solutions in these solvents.

Herbicidal solutions can often be dispersed as aerosols under high pressure.

However, preferred liquid herbicidal compositions are emulsifiable concentrates consisting of the active compounds of the invention and a solvent and an emulsifier as inert carrier.

Such emulsifiable concentrates can be spread with water and/or oil to any desired active compound concentration for use as a spray on weedy areas.

The emulsifiers most commonly used in these concentrates are nonionic surfactants or mixtures of nonionic and anionic surfactants.

Several emulsifier systems are used to create inverse (water-in-oil) emulsions;
Can be applied directly to weed-infested areas.

Typical herbicidal compositions of this invention are illustrated by the following examples.

Amounts are parts by weight. Example 7 Preparation of Powder (Duct) Production of Example 1 (Compound A) 10 Powdered Talc 90 The above compositions were mixed in a mechanical grinder and mixer to form a homogeneous, free-flowing powder with the desired particle size. Grinded until obtained.

This powder was suitable for direct application to weedy areas.

The compounds of this invention can be applied as herbicides by any art-recognized method.

One method of controlling weed growth consists of contacting a weed-infested area with a herbicidal composition comprising an inert carrier and a weedicidal effective amount of a compound of the invention as an essential active ingredient.

The concentration of the novel compounds of this invention in the herbicidal compositions varies widely depending on the type of formulation and the purpose of the formulation, but generally the herbicidal compositions of this invention contain about 0% of the active compounds of this invention.
．． Contains 05-95% by weight.

In a preferred embodiment of the invention, the herbicidal composition contains about 5-75% by weight of active compound.

The composition includes other neutralicides such as insecticides, nematicides, and fungicides;
Other substances such as stabilizers, spreaders, inactivators, adhesives, fixing agents, fertilizers, activators, synergists, etc. may also be included.

Such herbicides may also be used in the methods and compositions of this invention in the form of their salts, esters, amides and other derivatives when the parent compound is applicable.

Weeds are plants that grow in unwanted locations, have no economic value, and interfere with crop production, the growth of ornamental plants, or the welfare of livestock.

The novel compounds of this invention are particularly valuable for weed growth control because they are toxic to many types and groups of weeds, and relatively non-toxic to many beneficial plants.

The exact amount of compound required depends on a variety of factors, including the strength of the individual weed species, weather, soil type, application method, and the types of beneficial plants growing in the same area.

For example, application of as little as 1 to 2 ounces/kneeker of active compound is sufficient to adequately control slight overgrowth of weeds growing under unfavorable conditions; An application of 10 pounds per knee or more of active compound may be required to adequately control dense infestations of strong perennial weeds.

EXPERIMENTAL EXAMPLE 1 The herbicidal toxicity of the novel compounds of this invention was demonstrated by experiments conducted to examine the pre-emergence control of various weeds.

In these experiments, weed seeds were planted in small plastic greenhouse containers filled with dry soil.

At or before 24 hours after sowing, the containers were watered until the soil was moistened, and the test compound, formulated as an aqueous emulsion in acetone solution containing an emulsifier, was applied to the soil surface at the indicated concentration.

After spraying, place the soil container in greenhouse C to supply the necessary heat,
I then watered once a day or more frequently.

Plants were maintained under these conditions for 25-35 days and the condition and degree of damage of the plants were evaluated on a scale of 0-10.

0 = No damage 1.2 = Slightly damaged 3.4 = Moderate damage 5.6 = Slightly damaged 7.8.9 = Severely damaged 10 = Blight The effectiveness of the compounds of this invention is determined by the following data. shown.

Experimental Example 2 The herbicidal activity of Compound CD was investigated in the same manner as in Experimental Example 1.

Tables 2 and 3 show that the active ingredient was applied pre-emergent to weeds at a concentration of 10 lbs/neeker, and 14 lbs.
The results of the evaluation are shown below.

Table 4 shows the results of spraying after germination and evaluation 14 days after spraying.

The same criteria as in Experimental Example 1 were used to evaluate the damage.

Claims (1)

[Scope of Claims] 1. An inert carrier and a formula as an essential active ingredient [wherein,
is a halogen; R1 and R2 are independently a hydrogen atom or a lower alkyl group; Zlg and Z2 are independently an oxygen or sulfur atom; R3 and R4 are independently a hydrogen atom or a lower alkyl group; and m is 1 or 2. A herbicidal composition containing the anilide shown above in an amount toxic to weeds.