JPH02292205A - Herbicide composition - Google Patents

Abstract

PURPOSE:To obtain a herbicide composition containing N-(4-methyl-2- pyridyl)-2-[4-(4-cyanophenoxy)phenoxy]propionamide and N- pyrimidinylaminocarbonyl-5-pyrazole sulfonamide derivative as active ingredients. CONSTITUTION:The objective herbicide contains N-(4-methyl-2-pyridyl)-2-[4-(4 cyanophenoxy)phenoxy]propionamide and N-[(4,6-dimethoxypyrimidine-2-yl) aminocarbonyl)-4-ethoxycarbonyl-1-methyl-5-pyrazole sulfonamide in a weight ratio of 1:(0.001 to 1). Said herbicide exhibits excellent synergistic effect unexpected from each single component and also exhibits extreme weeding activity against not only initial stage of growth but also grown weed. Besides, said herbicide is able to kill many kinds of weed and exhibits large effect for annual weed such as Echinochloa crus-galli and perennial weed such as Scirpus juncoides without chemical injury to transplanted paddy rice.

Description

DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a herbicidal composition. [Prior Art] Many herbicides for rice cultivation have already been developed. However, there are still strong market demands for improved safety and reduced drug harm. In addition, many of the weeds in paddy fields are characterized by the fact that their emergence periods do not coincide, and they occur over a long period of time.At the time of herbicide application, the weeds are in various stages of growth, from those that have not yet emerged to those that have grown to some extent. There is usually a mixture of Therefore, there are problems such as it is not possible to obtain satisfactory results by applying conventional herbicides only once, and the herbicides have to be used several times. [Problems to be Solved by the Invention] Therefore, the object of the present invention is to provide a herbicide that, when used as a herbicide, has an excellent herbicidal effect on weeds that have not yet germinated to those that have grown to some extent at low doses. , maintain its effect for a long time,
The objective is to provide a highly safe herbicide for paddy rice. [Means for Solving the Invention] As a result of intensive research, the present inventors discovered that N-(4-methyl-2-pyridyl)-2- each independently has herbicidal activity.
[4-(4-cyanophenoxy)phenoxy]butylene amide and N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-4-ethoxycarbonyl-l-methyl-5-pyrazole sulfone This invention was completed after discovering that an excellent synergistic effect can be obtained by applying a mixture of amides. That is, this invention provides N-(4-methyl-2-pyridyl)-2-[4-(4-cyanophenoxy)phenoxy]propionamide and N-[(4.6-dimethoxypyrimidin-2-yl) [Aminocarbonyl]-4-ethoxyluponyl-l-methyl-5-pyrazole sulfonamide is provided as an herbicidal composition as an active ingredient. [Specific description of the invention] N-(4-methyl-2
-pyridyl)-2-(4-cyanophenoxy)phenoxy l-brobionamide (hereinafter referred to as compound A),
When applied alone as a herbicide for paddy fields, it has particularly high herbicidal activity against field weeds, one of the most harmful weeds in paddy fields, at the stage before weed germination. Moreover, a major feature of this drug is that it causes virtually no chemical damage to paddy rice. Note that Compound A can be produced by a known method. Furthermore, in direct-seeding rice cultivation, if Compound A is applied to both the leaves and the soil at the early stage of weed growth, it is possible to effectively control wild grass without causing any practical chemical damage to the direct-seeded rice. That is, it can be said that Compound A has remarkable intergeneric selectivity and is highly useful.

However, the herbicidal effect is not sufficient against weeds other than the grass family, and in order to expect a sufficient herbicidal effect against weeds that have grown to a certain extent, the dosage must be lower than when treating weeds before they germinate. Need a lot.

On the other hand, N-[(4.6
-dimethoxypyrimidin-2-yl)aminocarbonyl]-4-ethoxycarbonyl-l-methyl-5-pyrazole sulfonamide (hereinafter referred to as NC-3 1 1)
When used alone as a herbicide for paddy fields,
It is effective not only against annual weeds such as Japanese cypress and Japanese cypress, but also against perennial weeds such as Japanese cypress and Japanese cypress. Furthermore, it is highly safe for transplanted paddy rice, and is highly useful as a herbicide for paddy fields. However, the herbicidal effect on wild grasses is not complete. Note that NC-311 can be manufactured by a known method. The herbicidal composition of the present invention containing the above-mentioned compounds as active ingredients not only compensates for the shortcomings of each drug, but also exhibits an extremely significant synergistic effect, as is clear from the examples below. That is, compound A and NC-3
By using 1 and 1 in combination, the herbicidal effect of each compound is enhanced compared to when used alone. As a method for assaying the interaction between two active compounds,
The Colby calculation formula described in Weeds Vol. 15, pp. 20-22, 1967 is usually used.

However, X: herbicidal effect (%) when compound A is used in pg/a Y=
Herbicidal effect (%) when compound B is used at qg/a E=A.
B respectively p. Expected herbicidal effect {%} when mixed with qg/a If the actually measured herbicidal effect {%} exceeds E,
This indicates that the composition has a synergistic effect. As is clear from the results of Example 6 using Novie, which is one of the strongest weeds in paddy fields, the herbicidal effect (100%) of the herbicide composition of the present invention is higher than the expected herbicidal effect E (54%).
It is recognized that there is a synergistic effect. In other words, a high herbicidal effect can be achieved with a lower dose than would be expected from the herbicidal effect of each active ingredient alone.
The herbicidal composition of the present invention is not particularly limited to the blending ratio of each active ingredient (excellent synergistic effects can be obtained in a wide range of blending ratios, but preferably NC311 is added to 1 part by weight of compound A). (The blending ratio is about 101 to 1 part by weight.) In addition, the herbicidal composition of the present invention has remarkable herbicidal activity not only against weeds in the early stage of growth but also against weeds at a somewhat advanced stage of growth. One of its excellent features is that it has a wide range of suitable treatment periods, from the early weed germination period before and after rice planting to the weed growth period.Furthermore, there are many types of weeds that can be controlled, including Japanese knotweed, Japanese cypress, Japanese grasshopper, and Japanese grasshopper. It has a remarkable herbicidal effect on annual weeds such as lily and perennial weeds such as firefly, cyperus japonica, and urinary weed.Moreover, it is highly safe as it does not cause any chemical damage to transplanted paddy rice. When the herbicide composition of the present invention is actually used, compound A and NC-3
Appropriate amounts of each of 1 and 1 can be mixed with an inert carrier and used in various forms such as granules, fine granules, permanent formulations, emulsions, powders, and floor pulls, which are commonly used forms of agricultural chemicals.

Solid carriers include calcium carbonate, apatite, gypsum,
Mineral powders such as silica gel, vermiculite, mica, diatomaceous earth, talc, pyrophyllite, acid clay, clay, kaolinite, montmolystite, bentonite, white carbon, pumice powder, crystalline cellulose, starch, corn cob powder, Examples include vegetable powders such as walnut shells, polymeric compounds such as polyvinyl chloride and petroleum resins, and fine powders or granules such as urea and ammonium sulfate.

Examples of liquid carriers include alcohols such as methanol, ethanol, cyclohexanol, amyl alcohol, and ethylene glycol, aromatic hydrocarbons such as benzene, toluene, xylene, and medylnaphthalene, ketones such as acetone, isophorone, and cyclohexanone, and chlorobenzene. , halogenated hydrocarbons such as trichloroethylene, ethers such as ethylcellosolve, butylselonlube, dioxane, esters such as isobrovir acetate and benzyl acetate, polar solvents such as dimethylformamide and dimethyl sulfoxide, vegetable oils such as soybean oil and cottonseed oil. , kerosene,
Examples include mineral oil and water.

Furthermore, if necessary for the formulation, the reliability of the herbicidal effect can be increased by adding adjuvants or stabilizers used in agricultural chemicals, such as surfactants, spreading agents, and binders.

As a surfactant, alkylaryl sulfonate,
Anionic surfactants such as dialkyl sulfosuccinates, polyoxyethylene alkylaryl ether phosphate ester salts, alkyl sulfate ester salts, naphthalene sulfonic acid formalin condensates, etc. II. Examples include nonionic surfactants such as polyoxyethylene alkyl ether, polyoxyethylene polyoxybrobylene block copolymer, and sorbitan fatty acid ester. Examples of formulation aids include lignin sulfonate, alginic acid, polyvinyl alcohol, gum arabic, CMC (carboxymethyl cellulose), PAP (isobrobyl acid phosphate), and the like. The herbicide composition of the present invention may also contain an insecticide 5 as required.
It may contain fungicides, plant growth regulators, fertilizers, or other herbicides, or these may be used in combination. In particular, it may be appropriate to add and mix other herbicides to further improve the effectiveness of the herbicide. As a herbicide that can be added, 2,4-bis(ethylamino)-
6-ethylthio-1.3.5-1-riazine [common name:
Symetrine]. 2.4-bis(isobrobylamino)6
-Methylthio-1.3.5-1-Riazine [Generic name: Promethrin 1.2-(1.2-dimethylbrobylamino)-4-ethylamino-6-methylthio-1.3.5-
Triazine [generic name: triazine herbicides such as dimecmethrin 1: s-4-chlorobenzyl=N. N-diethyl carbamate [generic name: penthiocarb L. S-α
．． a-dimethylbenzyl=N. N-bentamethylenethiocarbamate [generic name. dimebiperate], S-benzyl-N-ethyl-N-(1,2-dimethylbubutyl) thiocarbamate [generic name: Esbubucarb]. S-ethyl hexahydride-IH-azevin-1-carbothioate [generic name: molinate]. O-3-tert-butylphenyl=N-(6-methoxy-2-pyridyl)-N
-Methylthiocarbamate [generic name: bibuticarb]
Carbamate herbicides such as 2,4-D. MCPB, 2
Phenoxy herbicides such as -(2-naphthyloxy)probionanilide [generic name: nabroanilide 1.2-(2,4-dichloro-3-methylphenoxy)probionanilide [generic name: clomeprop]; 2.4. 6-Trichlorophenyl=4-nitrophenyl ether [common name: chlornitrophenyl 1.2.4-dichlorophenyl=
3-methoxy 4-nitrophenyl ether [common name:
Clomethoxynil]. 2.4-dichlorophenyl=3-
Methoxycarbonyl-4-nitrophenyl ether [generic name: bifenox], 2-chloro-4-trifluoromethylphenyl 4-nitro-3-(terolahydrobilan-3-yloxy)phenoxy ether [reagent name:
Diphenyl ether herbicides such as MT-1241: N
Monobutoxymethyl-2-chloro-2°. 6°-Dietyl acetanilide [generic name: butachlor], N-bropoxyethyl-2-chloro-2°. 6°-diethylacetanilide [generic name: bretilachlor]. N-Methyl-2-(2-penzothiazolyloxy)acetanilide [generic name: mefenacet]
, 2°. 3°-Dichloro4-ethoxymethoxybenzanilide [Reagent name: HW-52]. N- (a.a.
-dimethylbenzyl)-2-promo 3.3-dimethylbutylamide [generic name: bromobutide], 3°. 4゜-
Amide herbicides such as dichlorpropylene anilide [generic name: brovanil]: l-(α,α-dimethylbenzyl)
-3- (4-methylphenyl)ure7 [ -119
Name: Timeron 1.1-(2-chlorobenzyl)-3
- (α.α-dimethylbenzyl)urea [Reagent name:
Urea herbicides such as JC-940 = 2-amino-3-
Chloro-1,4-naphthoquinone [generic name + quinone herbicides such as ACN1; 4-(2,4-dichloropenzoyl)-1,3-dimethyl-5-virazolyl p-toluenesulfonate [generic name: virazolate ], 4-(2.
4-dichlorobenzoyl)-1,3-dimethyl-5-phenacyloxyvirazole [generic name: virazoxyfen 1,4-(2,4-dichloro-3-methylbenzoyl)
-1,3-dimethyl-5-(4-methylphenaciloxy)virazole [generic name: benzofenatub], 5-benzyloxy-4-(2,4-dichlorobenzoyl)-1-methylvirazole [ Reagent name 2 NC-3101.
5-tert-butyl-3-(2,4-dichloro-5-
imbropoxyphenyl)-1.3. -41 year old Xadiazole-21(3H)1one [Common name dioxadiazonel, 3,7-dichloro8-quinolinecarvonelI! [
Generic name: 3-chloro-2-[2-fluor-4-chloro-5-(l-provinyloxy)phenyl]-4.5.6.7-tetrahydride-2H- Indazole [Reagent name: S-275]. 3-isobrobyl-2.1.3-penzothiadiazinone-4)-2.2-
Dioxide [Generic name: Benczone 1.1-(3-methylphenyl)-5-phenyl-IH-1.2.4-1 Riazole-3-carpoxamide [Reagent name: KNW-242
] Heterocyclic herbicides such as O. O-diisobuguchi building-2-
Examples include organophosphorus herbicides such as (benzenesulfonamide) ethylene dithiophosphate [common name: SAPI]. The application amount of the herbicide composition of the present invention varies depending on the application situation, application time, application method, target grass species, etc., but usually the amount of active ingredient of compound A per are is 1 to 50 g, preferably 2 to 50 g. 30g, and NC-311 is 0. Ol~20
g, preferably << is 0.1 to 10 g. Further, the application amount of the herbicidal composition of the present invention is usually 1.01 to 70 g, preferably 2.1 to 50 g in terms of the total amount of active ingredients per are.
It is.

The content of the total amount of active ingredients in the preparation is usually 1 to 90%, preferably 2 to 80% by weight. The present invention will be specifically explained below with reference to Examples, but the present invention is not limited to these Examples. In addition, in the following examples, "parts" indicate parts by weight. [Example] Example 1 Agent Compound A 10 parts NC-3
1 1 1 part diatomaceous ±
85 parts The above components were mixed and ground to prepare a wettable powder.

Italy 2 Crop Compound A 4 parts NC-311
0.2 parts Solbol 80OA
IO part xylene
δ5. Part δ The above components were mixed and dissolved to form an emulsion. 3 1 Compound A 4 parts NC-311
0.1 part bentonite
35 parts talc 3
7.9 parts Solbol 800A 3 parts After mixing and pulverizing the above ingredients, add an appropriate amount of water and knead.
After extruding through a sieve hole with a diameter of 0.7 mm and drying, 1 to 2
The pellets were cut into lengths of one meter to form granules.

Paddy field soil made into a paddy field by adding water to a plastic container with a diameter of 21c+a, sowing seeds of various weeds shown in Table 1 on the soil surface layer, and then paddy rice seedlings at the 2-leaf stage (variety: Nipponbare) After transplanting 2 plants to a depth of 1 cm, they were submerged with water to a depth of 2 cm and left in a greenhouse. Three days after transplanting the paddy rice (before the germination of the Japanese wildflowers) and seven days after transplanting the paddy rice (1.5 leaf stage of the Japanese wildflowers), a predetermined amount of granules of the herbicide of the present invention formulated according to Example 3 above was manually sprayed. In addition, each active ingredient compound was used alone as a comparison agent. Furthermore, for comparison, we also investigated the herbicidal effect without treatment. Three weeks after the chemical treatment, we investigated the herbicidal effect and the chemical damage to paddy rice, and Table 1 shows the results of the chemical treatment 3 days after rice transplantation, and Table 2 shows the results of the chemical treatment 7 days after rice transplantation. The herbicidal effect and phytotoxicity were evaluated according to the following criteria. ,,Effect Criteria 10: too% control 9: 90% control 8: 80% control 7: 70% control 6: 60% control 5: 50% control 4: 40% control 3: 30% control 2: 20% Pest control 1: to% control and vomiting 0% control l Hama JHL five rewards: Harmless + : Minor damage + : Minor damage + +z Medium damage +++ : Major damage The conditioned paddy soil was put in, seeds of various weeds and paddy rice seeds shown in Table 3 were sown on the soil surface layer, and then the soil was flooded with 2cII1 water, left standing in a greenhouse, and watered at appropriate times. The water in the container was drained 10 days after sowing. Next, a predetermined amount of the wetting powder of the herbicide of the present invention prepared according to Example 1 above was diluted with 20+ sl of water per pot, sprayed, and then left in a greenhouse. Two days after the chemical treatment, the plants were flooded with 2 cm of water and watered at appropriate times.
Three weeks after the chemical treatment, we investigated the herbicidal effect and chemical damage to paddy rice.2 The results are shown in Table 3. The same comparative agent as in Example 4 was used, and for comparison, the herbicidal effect in the case of no treatment was also investigated. The herbicidal effect and phytotoxicity were evaluated according to the standards of Example 4. Cross ball 1” area 1836c+n” f3 1・x 5 6 ca+
Fill a plastic container with paddy soil to a depth of 7 lbs.
A certain amount of wildflower seeds were sown. the next day. 3
The plants were grown in a greenhouse using c+s diving. Eight days after sowing, a predetermined amount of the herbicide composition of the present invention prepared according to Example 3 above was sprayed by hand, and then the plants were left standing in a greenhouse and watered at appropriate times. Thirty days after the chemical treatment, the remaining stems and leaves of the grasshoppers were cut and collected, their air-dry weight was measured, and the herbicidal effect was calculated using the following formula, and the results are shown in Table 4. Herbicidal effect (%) = Table 4 The same comparative agent as in Example 4 was used. [Effects of the Invention] As is clear from the results of Examples 4 to 6, the herbicidal composition of the present invention has significantly enhanced herbicidal power compared to when each component is applied alone. This is due to the cooperative effect between each active ingredient, and it is recognized that there is a significant synergistic effect.
That is, the greatest feature of the herbicide composition of the present invention is that
It is possible to obtain a high herbicidal effect that could not be predicted from the herbicidal effect of each active ingredient alone. In addition, the herbicide composition of the present invention exhibits remarkable herbicidal activity not only against weeds at the early stage of growth but also against weeds at a certain stage of advanced growth. One of its excellent features is that it has a wide range of suitable processing times. In addition, it controls a wide variety of vine weeds, and it has a remarkable herbicidal effect on annual weeds such as field weeds, cypress japonica, staghorn weed, and perennial weeds such as bulrushes. Moreover, it is highly useful as a safe and highly selective herbicide that does not cause chemical damage to transplanted paddy rice.

As described above, the herbicidal composition of the present invention has many excellent features and is highly practical.

Claims (2)

[Claims] (1) N-(4-methyl-2-pyridyl)-2-[4-
(4-cyanophenoxy)phenoxy]propionamide and N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-4-ethoxycarbonyl-1
- A herbicide composition containing methyl-5-pyrazole sulfonamide as an active ingredient. (2) Blending ratio is N-(4-methyl-2-pyridyl)-2
-[4-(4-cyanophenoxy)phenoxy]N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-4-ethoxycarbonyl-1-methyl-5- per 1 part by weight of propionamide The herbicidal composition according to claim 1, which contains 0.001 to 1 part by weight of pyrazole sulfonamide.