JPH0684288B2 - Herbicidal composition - Google Patents

Description

TECHNICAL FIELD The present invention relates to a novel herbicidal composition. In particular, the present invention relates to a herbicidal composition having good stability as an emulsifying pesticide.

(Problems to be Solved by Conventional Techniques and Inventions) Emulsifying pesticides are currently in great demand because they are easy to dilute and spray compounds having a medicinal effect as pesticides. Emulsifying pesticides are generally relatively easily obtained by diluting and mixing with a suitable solvent when the compound having a medicinal effect is liquid at room temperature. However,
When the compound having the medicinal effect was solid at room temperature, only a low concentration of the emulsifying pesticide was obtained unless the compound having the medicinal effect was readily soluble in the solvent. In addition, even if a high concentration of emulsifying pesticide is prepared under warm conditions, if the emulsifying pesticide is stored at low temperature or diluted with water at the time of use, the stability of the diluted solution will be poor The compound having the above medicinal effect may be broken out as crystals, or the uniformity of the emulsifying pesticide may not be maintained.
In such a case, the crystal causes clogging of the spraying device, cannot be used practically, and is inferior in commercial value.

On the other hand, the N-substituted-chloroacetamide compound is a compound having excellent properties especially as a herbicide for paddy fields. However, since many of the compounds are solid at room temperature,
When used as an emulsifying pesticide, there were the above-mentioned drawbacks.

(Means for Solving Problems) Therefore, the present inventors have conducted research for the purpose of using an N-substituted-chloroacetanilide compound having excellent properties as a herbicide as an emulsifying pesticide. The inventors have found that a composition of an N-substituted-chloroacetanilide compound and a sucrose ester compound is excellent as an emulsifying pesticide, and have completed the present invention.

That is, the present invention provides (A) general formula [Wherein Z is an alkoxyalkyl group, (However, R ₄ , R ₅ and R ₆ are the same or different hydrogen atom, halogen atom, alkyl group, alkoxy group, alkylthio group, alkoxyalkyl group or alkylthioalkyl group, and R ₇ and R ₈ are the same or different. Is a hydrogen atom or an alkyl group of), and R ₁ , R ₂ and R ₃ are the same or different hydrogen atoms, halogen atoms, alkyl groups, alkenyl groups,
An alkynyl group, an alkoxy group or an alkylthio group is shown. ] It is a herbicidal composition which uses N-substituted-chloroacetanilide and the (B) sucrose sugar ester compound represented by these as an active ingredient.

In the general formula (I), specific examples of the halogen atom represented by R ₁ , R ₂ , R ₃ , R ₄ , R ₅ and R ₆ include chlorine, bromine, fluorine and iodine atoms. The general formula (I)
In the above, the alkyl group represented by R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ and R ₈ may be linear or branched, and also has a carbon number. There is no particular limitation. Generally, the number of carbon atoms is preferably 1 to 6. Specific examples of the alkyl group include methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group, iso-butyl group, t-butyl group, n-pentyl group, n-hexyl group and the like. Is mentioned. The general formula (I)
Among them, the alkenyl group represented by R ₁ , R ₂ and R ₃ may be linear or branched, and the number of carbon atoms is not particularly limited. Generally, it is preferable that the carbon number is 2 to 4. Specific examples of the alkenyl group include a vinyl group, an allyl group, an iso-proper group, a 2-butenyl group and a 3-butenyl group. In the general formula (I), the alkynyl group represented by R ₁ , R ₂ and R ₃ may be linear or branched, and the number of carbon atoms is not particularly limited, but the same as the above. It is preferable that the number is 2 to 4. Specific examples of the alkynyl group include ethynyl group and 2-propynyl group. In the general formula (I), the alkoxy group represented by R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , and R ₆ is not particularly limited, but generally has 1 carbon atom.
-6 linear or branched, saturated or unsaturated groups are preferred. Specific examples of the alkoxy group which are generally suitably used include a methoxy group, an ethoxy group, an n-propoxy group, a t-butoxy group, an n-pentoxy group, an n-hexoxy group and an allyloxy group.

In the general formula (I), the alkylthio group represented by R ₁ , R ₂ , R ₃ , R ₄ , R ₅ and R ₆ is not particularly limited, but is generally a straight chain having 1 to 6 carbon atoms. Or branched saturated or unsaturated is preferred. Specific examples of the alkylthio group preferably used include methylthio group, ethylthio group, n
Examples include -propylthio group, t-butylthio group, n-pentylthio group, n-hexylthio group and allylthio group.
Further, in the general formula (I), the alkoxyalkyl group represented by Z, R ₄ , R ₅ and R ₆ is not particularly limited in carbon number,
A linear or branched saturated or unsaturated group having 2 to 6 carbon atoms is preferable. Specific examples of the alkoxyalkyl group include methoxymethyl group, methoxyethyl group, ethoxymethyl group, n-propoxymethyl group, n-propoxyethyl group, 1-methyl-2-methoxyethyl group, n-butoxymethyl group, Examples thereof include iso-butoxymethyl group, t-butoxyethyl group and allyloxyethyl group. Furthermore,
In the general formula (I), the alkylthioalkyl group represented by R ₄ , R ₅ and R ₆ is not particularly limited in the number of carbon atoms, but is a straight chain or branched saturated or unsaturated carbon atom having 2 to 6 carbon atoms. A saturated group is preferred, and specific examples of the alkylthioalkyl group include methylthiomethyl group, methylthioethyl group, ethylthiomethyl group, n-propylthiomethyl group, t-butylthioethyl group, allylthioethyl group and the like. Can be mentioned.

Among the above N-substituted-chloroacetanilides, Z is particularly The compound, which is a group represented by, is a solid at room temperature,
It is difficult to obtain high-concentration emulsifying pesticides. Therefore, the effect of adding the sucrose sugar ester compound is particularly great in the case of the above N-substituted-chloroacetanilide.

Also, Z is Among the N-substituted-chloroacetanilides represented by the formula, in the case where at least one of R ₄ , R ₅ and R ₆ is a halogen atom, an alkoxy group or an alkoxyalkyl group, a sucrose ester compound is added. This significantly improves the herbicidal effect.

As a method for producing the compound represented by the general formula (I) used in the present invention, a known method is adopted without particular limitation. For example, when Z in the general formula (I) is an alkoxyalkyl group, the method described in JP-B-41-9679 is used, and Z is In the case of the group represented by, it can be produced by the method described in JP-A-55-24194.

Furthermore, Z In the case of the group represented by, the following method is preferably adopted.

General formula, [Wherein R ₄ , R ₅ and R ₆ represent the same or different hydrogen atom, halogen atom, alkyl group, alkoxy group, alkylthio group, alkoxyalkyl group or alkylthioalkyl group, and R ₁ , R ₂ and R ₃ Represents the same or different hydrogen atom, halogen atom, alkyl group, alkenyl group, alkynyl group, alkoxy group or alkylthio group. ] The N-substituted aniline represented by the following formula is reacted with a chloroacetylhalogenide represented by the general formula, ClCH ₂ COX (where X represents a halogen atom), and is represented by the above general formula (I). The compound is obtained.

N-Substitution represented by the general formula (III) as a raw material
The aniline obtained by any method can be used.

In the reaction of the compound represented by the general formula (III) with chloroacetylhalogenide, the charged molar ratio of both compounds may be appropriately determined as necessary, but usually an equimolar amount or a slight excess of chloroacetylhalogenide is used. Is generally used.

In addition, hydrogen halide is produced as a by-product in the above reaction. Since this hydrogen halide reacts with the compound represented by the general formula (III) in the reaction system and causes a decrease in the product yield, it is usually necessary to allow a hydrogen halide scavenger to coexist in the reaction system. Is preferred. The scavenger for the hydrogen halide is not particularly limited, and known ones can be used. Examples of the scavenger that is generally preferably used include trialkylamines such as trimethylamine, triethylamine and tripropylamine; pyridine; sodium alcoholate; sodium carbonate, potassium carbonate, sodium hydrogen carbonate, magnesium carbonate and the like.

In the reaction, it is generally preferable to use an organic solvent. Examples of those suitably used as the solvent include:
Benzene, toluene, xylene, hexane, heptane,
Aliphatic or aromatic hydrocarbons such as petroleum ether, chloroform, methylene chloride, ethylene chloride or halogenated hydrocarbons; ethers such as diethyl ether, dioxane, tetrahydrofuran; ketones such as acetone, methyl ethyl ketone; acetonitrile, etc. Nitriles; N, N-dialkylamides such as N, N-dimethylformamide, N, N-diethylformamide; dimethylsulfoxide and the like.

The order of adding the raw materials in the reaction is not particularly limited, but generally, the compound represented by the general formula (III) is dissolved in a solvent, charged into a reactor, and chloroacetohalogenide dissolved in the solvent is added with stirring. Is good. Of course, it is also possible to continuously add the raw materials to the reaction system and continuously take out the produced reaction product from the reaction system.

The temperature in the reaction can be selected from a wide range, and it is generally sufficient to select it in the range of -20 ° C to 150 ° C, preferably 0 ° C to 120 ° C. Although the reaction time varies depending on the kind of the raw material, it is usually sufficient to select it in the range of 5 minutes to 10 days, preferably 1 to 40 hours. Further, it is preferable to stir during the reaction.

The method for isolating and purifying the desired product, that is, the compound represented by the general formula (I) from the reaction system is not particularly limited and a known method can be employed. For example, the reaction solution is cooled or allowed to cool naturally to room temperature or its vicinity, the reaction solvent and the remaining hydrogen halide scavenger are distilled off, and the residue is extracted with an organic solvent such as benzene, ether, or chloroform. By the above operation, the salt and the high molecular weight compound produced from the by-produced hydrogen halide and the hydrogen halide scavenger are separated. The organic solvent layer is dried with a desiccant such as Glauber's salt and calcium chloride, the organic solvent is distilled off, and the residue is vacuum distilled to obtain the desired product. In addition to isolation and purification by vacuum distillation, purification by chromatography, or when the product is a solid, can be performed by crystallization from a solvent such as hexane.

Further, the compound represented by the general formula (I) of the present invention has the general formula: [Wherein R ₄ , R ₅ and R ₆ are the same or different hydrogen atom, halogen atom, alkyl group, alkoxy group, alkylthio group, alkoxyalkyl group or alkylthioalkyl group, and R ₇ and R ₈ are the same or different. Is a hydrogen atom or an alkyl group, and X is a halogen atom. ] With a thiophene compound represented by the general formula [Wherein R ₁ , R ₂ and R ₃ are the same or different hydrogen atoms, halogen atoms, alkyl groups, alkenyl groups, alkynyl groups,
An alkoxy group or an alkylthio group is shown. ] It can also be obtained by reacting with chloroacetanilide.

The thiophene compound used as a raw material and the chloroacetanilide can be obtained by any method.
The conditions and the isolation and purification method for carrying out the reaction are the conditions and the isolation and purification used in the reaction between the N-substituted aniline represented by the general formula (III) and chloroacetylhalogenide described above. The conditions similar to the method can be adopted.

The other component of the herbicidal composition of the present invention is a sucrose ester compound. Known compounds can be used as the sucrose ester compound without any limitation. In particular, the general formula [However, X is the same or different hydrogen atom or an acyl group, and at least one is an acyl group. ] The sucrose ester compound represented by the following is preferably used in the present invention. In the sugar sugar ester compound represented by the general formula [II], the acyl group represented by X is preferably an alkyl group or an acyl group composed of a phenyl group and a carbonyl group.

The alkyl group may be linear or branched,
The number of carbon atoms is also not particularly limited. Generally, it is preferable that the carbon number is 1 to 6. Specific examples of the alkyl group include methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group, iso-butyl group, t-butyl group, n-pentyl group, n-hexyl group. Etc.

In the general formula [II], eight X's are present in the molecule, but at least one of these eight may be an acyl group. Usually, it is 4-8 for reasons such as easy availability.
A sugar sugar ester compound in which each X is an acyl group is preferably used.

The sucrose sugar ester compounds may be used alone or in combination of two or more.

The compounding weight ratio of the N-substituted-chloroacetanilide and the sucrose ester compound described above can be selected from a wide range, but usually, the sucrose ester compound is 0.5 parts by weight per 100 parts by weight of the N-substituted-chloroacetanilide. It is preferably 400 to 400 parts by weight, more preferably 5 to 100 parts by weight.

Further, in the present invention, in addition to the above-mentioned two components, a surfactant, a solvent and the like can be added if necessary. As the surfactant, a surfactant generally used in the field of agrochemical formulations is used without particular limitation. For example, anionic surfactants such as alkylbenzene sulfonate, β-naphthalene sulfonic acid formalin condensate and dialkyl sulfosuccinate, and polyoxyethylene alkyl allyl ether, polyoxyethylene allyl ether, polyoxyethylene alkyl ether, Further, nonionic surfactants such as polyoxyethylene alkylallyl ether sulphate and the like can be used alone or in admixture of two or more.

The solvent is not particularly limited, and known solvents can be used. For example, xylene, orthochlorotoluene, toluene, dimethylformamide, isophorone, ethylene glycol ethers and the like can be used alone or in combination of two or more.

The amount of the solvent used is not particularly limited, but 200 parts of the solvent is added to 100 parts by weight of the N-substituted-chloroacetanilide.
When used in the range of up to 1000 parts by weight, that is, when an emulsion having a relatively high concentration is used, the effect of the addition of the sucrose ester, which is one component of the herbicidal composition of the present invention, becomes remarkable, which is preferable. .

Furthermore, mineral oils, water, dispersants, spreading agents and the like, which are usually used in the preparation of agricultural chemicals, can be appropriately used if necessary.

[Action and effect]

The herbicidal composition of the present invention has excellent properties as an emulsifying pesticide. That is, crystals of N-substituted-chloroacetanilide do not crack even when stored at low temperature or diluted with water. Moreover, the homogeneity of the emulsion is not deteriorated by diluting with water. Further, the herbicidal effect of the herbicidal composition of the present invention as a herbicide is superior to that in the case of not containing a sucrose ester compound. Regarding low-temperature stability, it is presumed that the saccharose ester compound improved the solubility of N-substituted-chloroacetanilide in a solvent, but at present, the mechanism by which other effects are exerted is expressed. Not clear.

When using the herbicidal composition of the present invention as an emulsifying pesticide, it has an effect even if treated before and after germination of weeds,
High effects can be obtained in soil treatment and foliage treatment. Not only paddy fields, but also various cereals, beans, cotton, vegetables, fields, orchards, lawns, pastures, etc.
Widely useful in tea fields, mulberry fields, forest areas, non-agricultural areas, etc. Further, the herbicidal composition of the present invention sufficiently satisfies the properties required for an emulsifying pesticide, and its utility is extremely large.

In order to explain the present invention more specifically, formulation examples and examples of the preparation will be described, but the present invention is not limited to these examples.

Formulation Example Using the N-substituted-chloroacetanilide, the sucrose ester compound, the surfactant and the solvent shown in Table 1, various organic compound compositions were obtained under the conditions of heating at 40 ° C.

Calcium dodecylbenzene sulfonate was used as the anionic surfactant, and polyoxyethylene alkylallyl ether was used as the nonionic surfactant.

Further, N-substituted chloroacetanilide and saccharose ester are represented by the following structural formulas A and B, respectively.
The groups corresponding to X and X are shown in Table 1.

Example 1 50 cc of each of the organic compound compositions obtained in the formulation examples was placed in a 100 cc transparent glass sample bottle and allowed to stand in a thermostat at -5 ° C for 7 days, and then the presence or absence of crystal breakage was observed.

As a result, there was no change in any of the organic compound compositions No. 1 to 17, but considerable crystals were broken out in No. 18 and No. 19.

Example 2 The organic compound composition obtained in the formulation example was diluted with 250 times of water and allowed to stand for 2 hours, and the homogeneity of the emulsion and the presence or absence of crystal protrusion were observed.

As a result, all of the organic compound compositions Nos. 1 to 17 were uniform emulsions, and no crystal was projected. On the other hand, in No. 18, the degree of white turbidity was different between the upper part and the lower part of the emulsion, and the lower part had a greater degree of white turbidity. In addition, a large number of crystals were observed. No. 19 was about the same as No. 18.

Example 3 After putting alluvial soil in a 1/8850 ares Wagner pot, water was added and mixed to make a flooding condition with a water depth of 2 cm. The seeds of Novier and Firefly were mixed-sown in the above pot, and the tuber tuber tuber was further placed. The pots are placed in a greenhouse at 20 to 25 ° C to grow the plants, and on the 7th day after sowing, each organic compound composition is diluted so that Nopier has a predetermined amount of the drug at the 1-leaf stage, It was dropped with a pipette. Three weeks after the dropping, the herbicidal effect against various weeds was evaluated according to the following criteria, and the results are shown in Table 2.

Criteria 10: 100% weeding rate 9: 90-99% 〃 8: 80-89% 〃 7: 70-79% 〃 6: 60-69% 〃 5: 50-59% 〃 4: 40-49% 〃 3: 20 to 39% 〃 2: 10 to 19% 〃 1: 1 to 9% 〃 0: 0% 〃 Example 4 1/8850 ares Wagner pots were filled with field soil (planting loam soil), and various plant seeds were sown to a depth of 0.5 to 1 cm, and 20 to 25
It was grown in a greenhouse at 0 ° C. After 2 weeks, each organic compound composition was diluted and a predetermined amount of the foliage of each plant was spray-treated. After the treatment, the plants were grown in a greenhouse, and the herbicidal effect was evaluated after 2 weeks, and the results are shown in Table 3. The standard of herbicidal effect is the same as in Example 3.

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁵ Identification code Internal reference number FI Technical display location C07D 233/88 333/34 (A01N 43/56 43:16) (A01N 43/16 37:26 37 : 24 37:22 43:10)

Claims (1)

[Claims] 1. A general formula (A) [Wherein Z is an alkoxyalkyl group, (However, R ₄ , R ₅ and R ₆ represent the same or different hydrogen atom, halogen atom, alkyl group, alkoxy group, alkylthio group, alkoxyalkyl group or alkylthioalkyl group, and R ₇ and R ₈ represent the same or different. And R ₁ , R ₂ and R ₃ represent the same or different hydrogen atom, halogen atom, alkyl group, alkenyl group, alkynyl group, alkoxy group or alkylthio group. ] A herbicidal composition containing N-substituted-chloroacetanilide represented by the formula (B) and a sucrose ester compound (B) as active ingredients