JPS6135962B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention is represented by the general formula [] (In the formula, R is -OCH ₃ or

Represents [formula]. However, X represents a hydrogen atom or a halogen atom. ) α-(β-naphthoxy)propionic acid derivatives represented by the general formula (In the formula, R ₁ represents a lower alkyl group.) 2-chloro-2',6'diethyl-N-(alkoxyethyl)acetanilide as an active ingredient. The present invention relates to a drug composition. More specifically, by mixing the above-mentioned two components in an appropriate ratio, the usable period and herbicidal spectrum are significantly expanded compared to conventional paddy field herbicides. The object of the present invention is to provide an excellent herbicide composition that can be used at any time of the year and can also control perennial weeds that are difficult to control with conventional herbicides. Herbicides for paddy fields in Japan are roughly divided into three categories based on the timing of use: early-season herbicides, mid-season herbicides, and late-season herbicides, and the first two account for the majority of the amount used. Initial herbicides include MO (2,4,6-trichlorophenyl-4'-nitrophenyl ether) and NIP (2,4-dichlorophenyl-4'-nitrophenyl ether).
4'-nitrophenyl ether), and as a mid-term herbicide, Swep M [methyl-N-
[3,4-dichlorophenyl)carbamate and 2
-Methyl-4-chlorophenoxyacetic acid ethyl ester], Saturn S [S-(4-chlorobenzyl)-N,N-diethylthiol carbamate and 2-methylthio-4,6-bisethylamino-S-triazine admixtures] etc. Early stage herbicides are extremely effective when used at the beginning of weed emergence, but their effectiveness is significantly reduced when used during the peak weed emergence stage. Mid-season herbicides are effective from the weed germination stage to the growth stage, but when used during the germination stage, they cause significant chemical damage to paddy rice, and their use is limited to the period when the growth of paddy rice is considerably advanced. Furthermore, depending on the temperature and soil conditions, phytotoxicity or a decrease in efficacy can often occur. Furthermore, these herbicides are not sufficiently effective against perennial weeds, and instead encourage the growth of perennial weeds. Recently, from the point of view of labor saving in agricultural work, there has been a desire for the emergence of herbicides that can control all weeds in a single treatment and have a wide range of suitable application periods. There is no chemical agent that does not cause phytotoxicity to paddy rice during its entire growing period and that satisfies this requirement. The present inventors have conducted extensive research with the goal of developing a herbicide that can be used at any time from the beginning of weed germination to the growing season immediately after rice transplantation, exhibiting an appropriate control effect, and is harmless to paddy rice. As a result, a mixture of the compound represented by the above general formula [] and the compound represented by the general formula [] in an appropriate ratio exhibited an extremely significant herbicidal effect that far exceeded expectations, and each component alone could control the herbicide. It has a remarkable control effect not only on annual weeds, but also on the perennial weeds that have recently become more common, such as porcupine, bulrush, cypress, and black bream. The present invention was completed based on the discovery that there is no phytotoxicity at all. The dosage of the compound represented by the general formula [] and the compound represented by the general formula [], which are the active ingredients of the pesticidal composition of the present invention, can be significantly reduced compared to the dosage when each is used as a single agent. The appropriate mixing ratio of both component compounds is preferably 0.1 to 1 part by weight of the compound represented by the general formula [] to 1 part by weight of the compound represented by the general formula []. Specific examples of the compound represented by the general formula [] and the compound represented by the general formula [] used in the herbicidal composition of the present invention are as follows.

【table】

[Table] The composition of the present invention is most effectively formulated into granules for use. That is, the amount of the active ingredient is increased using bentonite, clay, talc, limestone, etc., and sodium lignin sulfonate, polyvinyl alcohol,
By adding a binder such as sodium alkylbenzene sulfonate, kneading with water, extrusion granulation and drying, or by dissolving in an appropriate solvent and uniformly adsorbing it onto granular diatomaceous earth, vermiculite, etc. , most preferably formulated as granules. The granules are uniformly dispersed by hand, using a granulator, from the ground, or from the air using a helicopter. In addition to granules, it may be formulated into wettable powders, powders, etc., and may be diluted with water or sprayed directly. Furthermore, if necessary, it is also possible to use them in combination with insecticides, fungicides, or other herbicides, or to formulate formulations. Next, examples of the present invention will be given, but the present invention is not limited thereto. All mixing ratios in the examples indicate weight ratios. Example 1 Granules 10 parts of compound A, 5 parts of compound E, 60 parts of bentonite
part, 21 parts of talc, 1 part of sodium dodecylbenzenesulfonate, 1 part of polyoxyethylene alkyl allyl ether, and 2 parts of sodium ligninsulfonate.
After mixing the two parts, add an appropriate amount of water, knead, and granulate using a granulator in the usual manner to obtain 100 parts of granules. Example 2 Granules 7 parts of compound B, 7 parts of compound D, 63 parts of bentonite
part, 30 parts of talc, 2 parts of naphthalene sulfonic acid mixture
1 part of dioctyl sulfosuccinate are mixed, an appropriate amount of water is added and kneaded, and the mixture is granulated using a granulator in a conventional manner to obtain 100 parts of granules. Example 3 Granules Compound C 8 parts, bentonite 32 parts, talc 52 parts
1 part, 2 parts of sodium ligninsulfonate, and 1 part of sodium dodecylbenzenesulfonate, then kneaded with an appropriate amount of water, granulated using a granulator in a conventional manner, and dried. This is impregnated with 5 parts of Compound F to obtain 100 parts of granules. Example 4 Granules 7 parts of compound B, 4 parts of compound E, 60 parts of bentonite
1 part, 26 parts of clay, 2.5 parts of sodium alkylbenzenesulfonate, and 0.5 part of polyvinyl alcohol are uniformly ground and mixed, then an appropriate amount of water is added and kneaded, and the mixture is granulated using a granulator in the usual manner.
Obtain 100 parts of granules. Example 5 Powder 9 parts of Compound B, 4 parts of Compound F, and 87 parts of a diatomaceous earth/clay mixture are mixed and ground to obtain 100 parts of a powder. Example 6 Wettable powder 30 parts of Compound A, 15 parts of Compound D, 10 parts of white carbon, 40 parts of diatomaceous earth, 3 parts of sodium ligninsulfonate, and 2 parts of sodium dodecylbenzenesulfonate were mixed and ground to make 100 parts of a wettable powder. get. The effects of the present invention will be specifically explained below using test examples. Test Example 1 Weed control test at the beginning of weed germination Fill an A/2000 Wagner pot with 11 kg of paddy soil, fertilize the entire layer with 1 g each of N, P ₂ O ₅ and K ₂ O with chemical fertilizers, and add an appropriate amount of water. Add and stir thoroughly to make a hydrated state. Two paddy rice seedlings (leaf age 2.5) grown in advance in a greenhouse are used as one plant, and each pot is seeded at a depth of 3 cm.
I sowed seeds of firefly and Heraomodaka. In addition, tubers of Urticaria japonica, Cyperus japonica, and Overwintered buds of Japanese cypress were transplanted to the plants, and they were grown in a greenhouse while maintaining the depth of sputum water at 3 cm. Three days after the seedlings were seeded, during the weed germination period, a predetermined amount of the test compound was treated using granules prepared according to the method shown in the above example. After treatment, a water leakage rate of 1 cm/day was given. One month after the chemical treatment, the amount of remaining weeds and the chemical damage to the paddy rice were investigated, and the results are shown in Table 1.

【table】

[Table] Test Example 2 Weeding test during the weed growing season A concrete pot measuring 50 cm x 50 cm x 50 cm was filled with an appropriate amount of paddy soil containing seeds and tubers of annual and perennial weeds from paddy fields, and N was added to the pot. , P ₂ O ₅ , and K ₂ O (3 g each) were applied to the entire layer with chemical fertilizers to create a stagnant state. In addition, leaf order 2.5
Two paddy rice seedlings were prepared per pot, and four plants per pot were transplanted at equal intervals. 17 days after rice planting, a predetermined amount of the test compound was treated under stagnant water using granules prepared according to the method shown in the above example. 5 days, 10 days, 20 days, and 1 month after the chemical treatment, the amount of weeds remaining in the pots and chemical damage to paddy rice were investigated. 5 days, 10 days after drug treatment and
The amount of weeds remaining after 20 days was compared with the amount of weeds remaining in the untreated area, and the degree of weed killing was evaluated on an 11-point scale [0 (no herbicide effect) to 10 (dead)], and the results were evaluated in the second
-a Table shows. In addition, the results after one month were measured by measuring the air-dry weight of the remaining weeds in the pot, and the results are shown in Table 2. During the test period, the water depth in the concrete pot was maintained at 3 cm, and water leaked at the equivalent of 1 cm per day for one month.

【table】

【table】

【table】

[Table] Test example 3 Field test Paddy fields in which common weeds naturally coexist were plowed and fertilized using the usual method (N, P ₂ O ₅ , K ₂ O 1 kg/each)
a) Plowing and leveling the land, 1 ward 10m ²
(2.5m x 4m), each with 2 young paddy rice seedlings at leaf age 2.5, 30cm apart between furrows, and 15 plants apart.
Transplanted in cm. After transplanting, while maintaining the water depth at 3 to 5 cm, test samples were prepared according to the method shown in the above example at the beginning of weed germination (3 days after rice planting) and at the 3.0 to 3.5 leaf stage of Japanese millet (15 days after rice planting). Mixtures of compounds or single granules were spread by hand. In addition, commercially available MO granules-9 and Saturn S granules were used as control drugs. The amount of weeds one month after spraying and the yield of paddy rice four months after spraying were investigated, and the results shown in Table 3 were obtained.

【table】

[Table] Test Example 4 Comparison during Weed Growth Period The following granules were prepared according to Example 4. The test compounds are indicated using the symbols described on pages 6 to 7. (1) Compound A/butachlor ⁽ * ⁾ granules
(7% + 4% active ingredient) (2) Compound B/butachlor ⁽ * ⁾ granules
(7% + 4% active ingredient) (3) Butachlor (4% active ingredient) (4) Compound B (7% active ingredient) (5) Compound E (4% active ingredient) (6) Compound F (4% active ingredient) ) (7) Compound A/Compound E (7%+4% active ingredient) (8) Compound B/Compound E (7%+4% active ingredient) (9) Compound B/Compound D (7%+4% active ingredient) ( 10) Compound B/Compound F (7% + 4% active ingredient) (*) Butachlor is the compound 2-chloro-2'·6'-diethyl-N-(butoxymethyl)acetanilide described in JP-A-51-38419. It is. Fill an A/500 pot with an appropriate amount of paddy soil in which plants such as Japanese millet grass and green grass naturally occur, and add N,
Fertilize the entire layer with P ₂ O ₅ and K ₂ O 0.5 g with chemical fertilizer,
It was in a stagnant state. Add 1 paddy rice seedling of leaf age 2.5 to this.
Two plants were prepared, and the two plants were transplanted per pot. When the weeds had grown to the size of about two leaves, 250 g/a of each granule was applied to the soil under stagnant water. On the 5th, 10th, and 20th day after spraying the chemical, the amount of remaining weeds was compared with the untreated plot, and the degree of weed killing was evaluated on an 11-point scale [0 (no weed killing effect) to 10 (death)]. Indicated. The results are shown in Table 4.

[Table] From the results shown in Table 4, the herbicide composition according to the present invention is more effective than the herbicide composition (admixture of compound A or B and butachlor) described in JP-A-51-38419. compound (compound A or B and compound D, E
(or a mixed composition with F) is not much different in terms of phytotoxicity to paddy rice transplanted to young seedlings, but it is clear that it is rapidly effective against weeds, especially weeds. Test Example 5 Prepare a pot similar to Test Example 4, and add each granule prepared in Test Example 4 equivalent to 250g/a or 100g/a when the weeds have grown to about one leaf.
a. The particles were mixed in an amount equivalent to 150 g/a, and the soil was treated under stagnant water. Drug treatment days 10, 20 and 30
The degree of weed killing was investigated on the second day. The evaluation method was the same as in Test Example 4. The results are shown in Table 5.

[Table] From the results shown in Table 5, it is found that the herbicide composition according to the present invention ( A mixture of Compound B and Compound E or F) has a fast onset of herbicidal effect, is fast-acting, and has high activity.It has especially enhanced herbicidal power against Urikawa, and can be used at low dosages. It is clear that the difference is large. From Tables 4 and 5, compound A or B and butachlor [2-chloro-2'·6'-diethyl-N
-(butoxymethyl)acetanilide], compared to the herbicide described in JP-A-51-38419, which is a mixture of compound A or B and 2-chloro-2'.6'-
The herbicidal composition of the present invention mixed with diethyl-N-(alkoxyethyl)acetanilide exhibits herbicidal activity quickly, has high herbicidal activity even at a small dose, and is highly synergistic. As is clear from the above results, the composition of the present invention is harmless to paddy rice even if it is used at any time from the beginning of weed germination to the peak of weed growth immediately after rice transplantation, and moreover, it can be applied only once. It can control all weeds and is significantly superior to conventionally used herbicides. Since the composition of the present invention is excellent in quick-acting properties,
It eliminates farmers' anxiety about the weeding effect that occurs when the weeding effect is slow, avoids unnecessary double spraying due to this anxiety, suppresses wasted labor and expense consumption, and improves agricultural work and farm management. There are many points that contribute to this. Additionally, conventional herbicides differ from fungicides and insecticides;
Because there is a difference in the growth of weeds even after 3 to 4 days of rice planting, the timing of spraying must be adjusted, making mechanized spraying over a wide area impossible, and labor-saving in agricultural work is hindered. The reality is that Since the composition of the present invention has a significantly long suitable period of use, it can be applied at the same time as rice planting even if the rice planting period is around 10 to 20 days. Therefore, joint application over a wide range is possible, and in this respect, it also requires less effort. It greatly contributes to the reduction of

Claims (1)

[Claims] 1. General formula (In the formula, R represents -OCH ₃ or [Formula], and
−Naphthoxy)propionic acid derivatives and general formula (In the formula, R ₁ represents a lower alkyl group.) 2-chloro-2',6'-diethyl-N-(alkoxyethyl)acetanilide as an active ingredient. Herbicide composition.