JPH06172108A - Herbicidal composition - Google Patents

Abstract

PURPOSE:To obtain a herbicidal composition capable of manifesting remarkable synergistic effects by combining an N-acyl-N-phenyltetrahydrophthalamic acid derivative with any of naproanilide, dymron, bromobutide and JC-940. CONSTITUTION:This herbicidal composition is obtained by combining at least one of N-acyl-N-phenyltetrahydrophthalamic acid derivatives of the formula [X and Y are H or halogen; Ar is phenyl or naphthyl; R<1> is H, halogen, alkyl, alkoxy, etc.; R<2> is H or alkyl; R<3> is OH, alkoxy or alkenyloxy; (m) is 0-5] with at least one of 2-(2-naphthyloxy)propionanilide (naproanilide), 1-(alpha,alpha- dimethylbenzyl)-3-(4-methylphenyl)urea (dymron), 2-bromo-N-(alpha,alpha- dimethylbenzyl)-3,3-dimethylbutanamide (bromobutide) and 1-(2- chlorobenzyl)-3-(alpha,alpha--dimethylbenzyl)urea (JC-940).

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention relates to a herbicidal composition, and more particularly to N-aryloxyacyl-
At least one compound selected from N-phenyltetrahydrophthalamic acid derivatives, 2- (2-naphthyloxy) propionanilide (hereinafter referred to as "naproanilide"), 1- (α, α-dimethylbenzyl)-
3- (4-methylphenyl) urea (hereinafter, referred to as "Dimuron"), 2-bromo-N- (α, α-dimethylbenzyl) -3,3-dimethylbutanamide (hereinafter, referred to as "bromobutide"). , 1- (2-chlorobenzyl)
-3- (α, α-dimethylbenzyl) urea (hereinafter,
It is called "JC-940". And at least one compound selected from the above) as an active ingredient.

[0002]

2. Description of the Related Art At present, many herbicides have been put into practical use as herbicides for paddy fields, which contributes to labor saving of weeding work and improvement of crop productivity. However, there is a demand for the development of a new drug having superior herbicidal properties such as safety against rice, complete weeding effect against a wide variety of paddy field weeds, and further labor saving of weeding work.

Further, the herbicidal period is prolonged due to changes in the cultivation system, and herbicides are repeatedly used several times. Due to such a large amount of application, the herbicides remain in the soil or flow out to rivers. It is causing problems.

In order to solve such problems, various herbicides are still being actively developed, and the applicant of the present invention is represented by the general formula (I) in the specification of the patent application filed at the same time as the present application. It was clarified that these compounds have excellent herbicidal effects at low doses as compared with conventional herbicides and have high safety against rice. At the same time, it was found that the herbicidal effect not only extends to many types of paddy weeds, but also has the characteristic that the effect is maintained for a long period of time after treatment. Could not be said to have a sufficient effect.

On the other hand, it has been known that the conventionally known herbicide naproanilide is effective against broad-leaved weeds and Cyperaceae weeds, and that dimuron, bromobutide and JC-940 are effective against Cyperaceae weeds. But,
Since the herbicidal spectrum was narrow, there were cases where sufficient effects could not be obtained when used alone. Further, there is a problem that it is used in a considerably higher dose than the compound represented by the general formula (I).

[0006]

Means for Solving the Problems The present inventor has conducted research to make the compound represented by the general formula (I) as a more excellent herbicide, and as a result, the compound represented by the general formula (I) has been changed to a conventional herbicide. The present invention has been completed by discovering that a significant synergistic effect appears by incorporating the above-mentioned herbicide used.

That is, the present invention has the general formula (I)

[0008]

[Chemical 2]

(Wherein X and Y independently represent a hydrogen atom or a halogen atom, Ar represents a substituted or unsubstituted phenyl group or naphthyl group, R ¹ represents a hydrogen atom,
Represents a halogen atom, a lower alkyl group, a lower alkoxy group, a lower alkenyloxy group, a lower alkynyloxy group, a lower alkoxyalkoxy group or a lower alkoxycarbonylalkoxy group, R ² represents a hydrogen atom or a lower alkyl group, and R ³ represents hydroxyl. Represents a group, a lower alkoxy group, a lower alkenyloxy group, a lower alkynyloxy group, a lower alkoxyalkoxy group, a benzyloxy group or a lower alkoxycarbonylalkoxy group. m is an integer and represents 0 to 5. ) At least one compound selected from the group consisting of N-aryloxyacyl-N-phenyltetrahydrophthalamic acid derivatives and naproanilide, dimuron, bromobutide, J
A herbicidal composition comprising at least one compound selected from C-940 as an active ingredient.

The synergistic effect of each component in the present invention is remarkable, and for example, each single drug constituting the herbicide composition is sufficiently effective against fly and firefly even at a concentration at which it cannot exert its effect by itself. It is possible to express a good herbicidal effect. Therefore, the amount of the herbicide used can be reduced, and as a result, not only the safety for rice can be increased but also the effect on the environment can be minimized, which is extremely useful. In addition, it was also found that the herbicidal composition of the present invention has an excellent property that the residual effect is remarkably long as compared with the use thereof alone.

By the way, the herbicidal composition of the present invention exhibits an effect even when the weeds are treated before germination or after germination, and a high effect is obtained also in the soil treatment and the foliage / soil treatment. Furthermore, it is also useful for various cereals other than rice, other fields, forests, tank yards, track ends,
It can also be applied to the control of various weeds in non-agricultural land, etc., and has a great economic effect in controlling weeds.

The herbicidal composition of the present invention usually depends on the relative activity of each component, but usually 0.001 of the compound represented by the general formula (I) per part by weight of naproanilide, dimuron, bromobutide or JC-940. ˜50 parts by weight, preferably 0.001 to 10 parts by weight.
Further, the herbicidal composition of the present invention has a ratio of the compound represented by the general formula (I) relatively lower than that of other herbicides,
For example, the amount of the compound represented by formula (I) is more preferably 0.001 to 0.1 part by weight per 1 part by weight of the other herbicide to be incorporated.

The application rate of the composition of the invention depends on a number of factors,
For example, the amount of 0.001 to 10 Kg / ha is generally appropriate, although it depends on the type of the particular target plant whose growth is to be stopped. A person skilled in the art can easily determine an appropriate usage rate by a standardized normal test without performing a large number of experiments.

The compositions according to the invention are preferably used in the form of compositions in which the active ingredient is mixed with a carrier which comprises a solid or liquid diluent. Next, Table 1 shows typical examples of the compound represented by formula (I) in the present invention. These compounds are included in the compound represented by the general formula (I), but the compound represented by the general formula (I) is not limited thereto.

[0015]

[Table 1]

The individual active compounds represented by the general formula (I) may have their respective herbicidal activities, but in that case, the herbicidal activity when two active compounds are combined is two of those. This can be said to be synergistic when it is greater than the simple sum of the activities of each of the compounds (expected activity). The expected activity of a particular combination of two herbicides can be calculated as follows. (See Colby SR, "Calculating Synergistic and Antagonistic Responses of Herbicide Combinations", Weed, 15: 20-22, 1967). α: Inhibition rate when herbicide A was treated with aKg / ha β: Inhibition rate when herbicide B was treated with bKg / ha E: Herbicide A was aKg / ha, herbicide B It can be said that the inhibition rate expected when treated with the amount of bKg / ha, that is, if the actual inhibition rate is larger than the above calculation, the combined activities show a synergistic effect.

[0017]

EXAMPLES The present invention will be described in more detail with reference to the following examples, but the compounds, dosage amounts, dosage forms and the like in the present invention are not limited to the examples. All "parts" mean parts by weight.

Formulation Example 1 Granule Compound No. 3 0.2 parts Naproanilide 7 parts Bentonite 50 parts Talc 42.8 parts The above components are uniformly mixed and pulverized, and then a small amount of water is added and the mixture is kneaded with stirring to form an extrusion molding. Granulate with a granulator and dry to give granules.

Formulation Example 2 Granule Compound No. 4 0.3 part Daimlon 7 parts Bentonite 50 parts Talc 42.7 parts The above components are uniformly mixed and pulverized, and then a small amount of water is added and the mixture is kneaded with stirring to form an extrusion type product. Granulate with a granulator and dry to give granules.

Formulation Example 3 Granule Compound No. 2 0.5 parts Bromobutide 5 parts Bentonite 50 parts Talc 44.5 parts The above components are uniformly mixed and pulverized, and then a small amount of water is added and the mixture is kneaded with stirring to form an extrusion molding. Granulate with a granulator and dry to give granules.

Formulation Example 4 Granule Compound No. 1 0.2 parts JC-940 5 parts Bentonite 50 parts Talc 44.8 parts The above materials are uniformly mixed and pulverized, and then a small amount of water is added, and the mixture is kneaded with stirring, kneaded and extruded. Granulate with a granulator and dry to make granules.

Formulation Example 5 Wettable powder compound No. 1 1 part Daimlon 20 parts Dikrite A 75 parts (Kaolin-based clay: product name of Sikhlite Industrial Co., Ltd.) Sorpol 5039 2 parts (Nonionic surfactant and anion Mixture with water-soluble surfactant: Toho Chemical Co., Ltd. trade name Carplex (anti-caking agent) 2 parts (White carbon: Shionogi Seiyaku Co., Ltd. trade name) And

Formulation Example 6 Wettable powder compound No. 2 1 part JC-940 30 parts Dekwright A 65 parts (Kaolin-based clay: trade name of Sikhlite Industry Co., Ltd.) Solpol 5039 2 parts (nonionic surfactant And anionic surfactant: Toho Chemical Co., Ltd. trade name Carplex (anti-caking agent) 2 parts (white carbon: Shionogi Seiyaku Co., Ltd. trade name) Use as a Japanese medicine.

Test Example 1 Herbicidal effect test under flooded condition Paddy soil (alluvial soil) was put in a 1/5000 ares Wagner pot, and water was added to mix. The soil surface was sown with seeds of Novier, Firefly, Pleurotus cornucopia, and broad-leaved weeds such as eel, azalea, and yellow cypress. Rice seedlings at the 2.5 leaf stage were further transplanted to a depth of 2 cm, and then grown in a glass room at 20 to 25 ° C. under a flooded condition of a water depth of 3 cm. Three days after rice transplantation, the wettable powder was diluted with water, and then a prescribed amount was dropped. After 3 weeks, the above-ground fresh weight of each weed remaining and the above-ground fresh weight of the untreated plot were measured in order to see the phytotoxicity and herbicidal effect on rice, and the inhibition rate was calculated according to (2). Results are graded from 0 to 5 according to the following criteria,
The results are shown in Tables 2 and 3.

[0025] Judgment criteria Score Suppression rate 5 100% (Complete death) 4 70-99% 3 40-69% 2 20-39% 15-19% 05 Less than 5% (almost no effect)

[0026]

[Table 2]

[0027]

[Table 3]

Test Example 2 Test of Synergistic Effect on Firefly The paddy soil (alluvial soil) was filled in a Wagner pot of 1/5000 are and seeds of firefly were sown on the surface layer. It was grown in a glass chamber at 20 to 25 ° C. under a flooded condition of a water depth of 3 cm. Three days after seeding, a wettable powder diluted solution of each drug was treated dropwise, and after 3 weeks, the above-ground fresh weight of the remaining firefly and the above-ground fresh weight of the untreated section were measured. The inhibition rate was calculated by (Equation 2), and the experimental results with the single compound and the complex drug are shown in Table 4 as the actually measured values. In addition, the numerical value calculated from the inhibition rate of the single compound in Table 4 according to (Equation 1) is shown as the calculated value. From the comparison of these numerical values, it is clear that the herbicidal composition of the present invention exceeds the inhibition rate expected from each single compound.

[0029]

[Table 4]

[0030]

As is clear from the results of the examples, the general formula (I)

[0031]

[Chemical 3]

(Wherein, X and Y independently represent a hydrogen atom or a halogen atom, Ar represents a substituted or unsubstituted phenyl group or naphthyl group, R ¹ represents a hydrogen atom,
Represents a halogen atom, a lower alkyl group, a lower alkoxy group, a lower alkenyloxy group, a lower alkynyloxy group, a lower alkoxyalkoxy group or a lower alkoxycarbonylalkoxy group, R ² represents a hydrogen atom or a lower alkyl group, and R ³ represents hydroxyl. Represents a group, a lower alkoxy group, a lower alkenyloxy group, a lower alkynyloxy group, a lower alkoxyalkoxy group, a benzyloxy group or a lower alkoxycarbonylalkoxy group. m is an integer and represents 0 to 5. )) And an N-aryloxyacyl-N-phenyltetrahydrophthalamic acid derivative represented by the formula) and at least one compound selected from naproanilide, daimuron, bromobutide and JC-940 are not expected to be applied individually. It brings about a remarkable synergistic effect and can kill many kinds of target weeds at a low application rate.

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁵ Identification code Internal reference number FI Technical indication (A01N 37/30 37:18) (A01N 37/30 47:28) (72) Inventor Tadashi Yamaoka Next 2805 Imafuku Nakadai, Kawagoe City, Saitama Prefecture Central Glass Co., Ltd. Tokyo Research Laboratory (72) Inventor Yukio Ikeda 3741-11 Shimookamoto, Kawachi Town, Kawachi District, Tochigi Prefecture (72) Inventor Matsumura Kawamura 2805, Imafuku Nakadai, Kawagoe City, Saitama Prefecture Address Central Glass Co., Ltd. Tokyo Research Institute (72) Inventor Takeo Furumata 2805 Imafuku Nakadai, Kawagoe City, Saitama Prefecture Central Address Glass Co., Ltd. Tokyo Research Institute (72) Inventor Kaoru Mori 2805 Imafuku Nakadai, Kawagoe City Saitama Prefecture Centra Le Glass Co., Ltd. Tokyo Research Center

Claims (1)

[Claims] 1. A compound represented by the general formula (I): (In the formula, X and Y each independently represent a hydrogen atom or a halogen atom, Ar represents a substituted or unsubstituted phenyl group or a naphthyl group, and R ¹ represents a hydrogen atom, a halogen atom, a lower alkyl group or a lower alkoxy group. , A lower alkenyloxy group, a lower alkynyloxy group, a lower alkoxyalkoxy group or a lower alkoxycarbonylalkoxy group, R ² represents a hydrogen atom or a lower alkyl group, and R ³ represents a hydroxyl group, a lower alkoxy group, a lower alkenyloxy group. , A lower alkynyloxy group, a lower alkoxyalkoxy group, a benzyloxy group or a lower alkoxycarbonylalkoxy group, m is an integer and represents 0 to 5), N-aryloxyacyl-N-phenyltetrahydrophthalamine Selected from among acid derivatives Kutomo one compound and 2- (2
-Naphthyloxy) propionanilide, 1- (α, α
-Dimethylbenzyl) -3- (4-methylphenyl) urea, 2-bromo-N- (α, α-dimethylbenzyl)
At least one compound selected from -3,3-dimethylbutanamide and 1- (2-chlorobenzyl) -3- (α, α-dimethylbenzyl) urea is contained as an active ingredient. A herbicidal composition.