JPH01165503A - Herbicidal composition - Google Patents

Abstract

PURPOSE:To obtain a herbicide, containing an N-[1-(thienyl)ethyl]amine derivatine, pyrazole derivative and chloramide or cumylurea derivative, usable in any periods without phytotoxicity to paddy rice and having an extended weeding spectrum. CONSTITUTION:A herbicidal composition, containing a compound expressed by formula I [Z is halogen, lower alkyl, etc.; n is 0, 1 or 2; R is formula II (X and Y are H, alkyl, etc.), etc.], a compound expressed by formula III (R<1> is H or CH3; R<2> is formula IV, etc.; Q is CH3 or Cl; k is 0-3) and a compound expressed by formula V [R is expressed by the formula -CB(Br)-C(CR3)3, etc.] and adjusted so as to respectively apply 30-300g compound expressed by formula I, 90-300g compound expressed by formula III and 30-300g compound expressed by formula V by weight ratios per 10 ares. This composition is usable in any period simultaneously or just after seeding or transplanting to growth period of weeds in paddy field without phytotoxicity and capable of controlling annual, perennial weeds to duckweeds and algae.

Description

Detailed Description of the Invention [Field of Industrial Application] The present invention relates to a herbicide composition, and more specifically to a herbicide composition that has lower chemical damage than conventional herbicides for paddy fields, has a wide range of suitable periods for use, and has a significantly improved herbicidal spectrum. In other words, any rice cultivation technique can be used without harm to rice at any time, from the time of sowing or transplanting of rice or immediately after, until the growing season of rice field weeds, and can be used to control not only annual but also perennial weeds, duckweed, and algae. The present invention relates to an excellent rice paddy herbicide composition that can control all types of herbicides.

[Prior art] Recently, herbicides for rice fields have made remarkable progress, and have a wide herbicidal spectrum that can control from annual to perennial weeds with a single treatment, and can be used at any time from the beginning of weed emergence to the growing season. So-called early-to-mid-stage herbicides that can be used even in the early and middle stages have been developed and are beginning to be used.

However, it cannot be said that the development of herbicides that are harmless to paddy rice at any time of the year is still insufficient. That is, there is a desire for a herbicide that does not cause chemical damage throughout the entire growing period of rice, has a wide herbicidal spectrum, and has a suitable treatment period.

On the other hand, in recent years, 90% of farmers have become part-time farmers. Furthermore, from the perspective of the international economy, there is a strong demand for the development of labor-saving techniques in wet rice cultivation, and direct sowing techniques, particularly direct sowing in flooded and submerged soil, have been taken up. It is thought that its importance will continue to increase in the future.

In direct flooding (in the soil), rice seeds are germinated directly in the rice field, and the germination starts at the same time as other weeds, so without herbicides, the vigorously growing weeds will prevent the rice from growing. Significantly inhibited. After germination, seedlings are disturbed by peeling off the topsoil and water temperature drops due to algae, which impedes growth. Topsoil peeling and algae often appear especially in the early stages of seed growth, and not only directly sown rice but also transplanted areas are affected by it.

Triazine herbicides and 2-amino-3-chloro-1,4-
Naphthoquinone (ACN) is known, but triazine herbicides depend on the timing of application.

There is a risk of phytotoxicity when using ACN, and ACN has problems with the appropriate processing time and fish toxicity. In addition, pyrazole herbicides, which are harmless to rice seed germination and can be used for direct sowing, are not only unable to suppress topsoil flaking and algae growth, but are also known to promote these conditions depending on the conditions. Ori,
In addition, it has the disadvantage that it is not sufficiently effective against some broad-leaved xL grasses and Cyperaceae weeds, and is significantly less effective against weeds during the growing season. Although there is a desire for a herbicide that can be used at any time from the time of sowing or transplanting to the weed growing season and can be used to control all weeds, duckweed, and even algae in a single treatment, However, none of the existing herbicides satisfies this requirement.

[Objective of the Invention] Under these circumstances, the present inventors have discovered that not only seedling transplant cultivation but also cultivation techniques such as direct sowing in warm water and direct sowing in flooded soil can be applied to paddy rice without chemical damage, and that We have conducted extensive research with the goal of developing a herbicide that can be used at any time from the time of sowing or transplanting to the weed growing season, and can be used to control all weeds, duckweed, and even algae in a single treatment.

[Structure of the invention] Among them, certain N-El-(thienyl)ethyl]
Mixed compositions of amine derivatives, certain pyrazole derivatives, and certain cumylamide or cumylurea derivatives have additive effects on target weeds, including topsoil removal, algae, and duckweed control effects, in addition to the additive effects of each single use. In some cases, the herbicidal activity inherent to pyrazole derivatives and cumylamide or cumylurea derivatives is accelerated, significantly expanding the herbicidal spectrum and the range of suitable treatment periods. Based on this knowledge, we have completed the herbicide of the present invention, which is safe and has a wide herbicidal spectrum as a herbicide for direct sowing (in soil) to early to mid-stage treatment.

That is, the herbicidal composition of the present invention contains, as an active ingredient, the general formula: [wherein Z is a halogen, a lower alkyl group, or a lower alkoxy group, and n is 0, l or 2, (provided that X and Y are the same or different, hydrogen, a straight chain or branched lower alkyl group (X and Y may form a ring), a straight chain or branched lower haloalkyl group, a straight chain or branched lower alkoxy group, A linear or branched lower alkoxymethyl group, or a halogen,
X and Y are not hydrogen at the same time. ), or represents. ] At least one N-[1-(thienyl)ethyl]amine derivative represented by the general formula: [where nl is hydrogen or a methyl group, and R8 is the formula: Q represents an integer of 0 to 3 for a methyl group or chlorine. ] At least one pyrazole derivative represented by the general formula: [wherein, R represents a group represented by the formula: Br CHs - CH-CCHs, CHs or]. ] Contains at least one kind of cumylamide or cumylurea derivative represented by the following.

It is known that pyrazole derivatives (II) exhibit herbicidal activity (for example, Japanese Patent Publication No. 54-36648, Japanese Patent Publication No. 56-28885, Japanese Patent Publication No. 62-19402, and Japanese Patent Application Laid-open No. 185568/1983). reference). Pyrazole derivatives are mainly effective at the beginning of growth of annual and perennial weeds, but their effectiveness varies widely depending on the conditions, and their activity may be particularly unstable against Cyperaceae and annual broad-leaved weeds. In addition, it is not possible to suppress topsoil peeling and the occurrence of algae and duckweed.

Next, cumyl urea derivative (Il
l) is also known to exhibit herbicidal activity (for example,
See Japanese Patent Publication No. 56-43455. ).

Cumylamide or cumylurea derivatives are mainly effective against annual and perennial cyperaceous weeds (such as cyperus, cyperus, and cyperus), but are not effective against other grasses, broad-leaved grasses, or advanced-growing cyperaceous weeds. Significantly inferior.

In addition, it is not possible to suppress the peeling of topsoil and the occurrence of algae and duckweed.

On the other hand, N-[1-(thienyl)ethylcoamine derivative (
1) is a new compound, patent application No. 6l-145472 (
(filed on June 21, 1986), the manufacturing method thereof is described and claimed as a patent. This derivative (+) has no phytotoxicity on rice, shows activity against broad-leaved weeds, algae,
It is possible to suppress the occurrence of duckweed and topsoil peeling. On the other hand, it is less effective against flat leaf and perennial weeds.

Novel N-[1-(thienyl)ethyl] used in the present invention
The amine derivative (1) can be produced, for example, according to the following reaction formula.

[In the formula, R, Z and n have the same meanings as above, and W represents halogen. ] In this reaction, the reaction is usually carried out using benzene, diethyl ether, chloroform, acetone, tetrahydrofuran, dioxane, etc. as a solvent, and triethylamine, pyridine, N,N,-dimethylaniline, N-methylmorpholine, etc. as an acid acceptor. -20 to 5 as temperature
0°C is preferably employed.

Preferred examples of amine derivatives (I) are as follows. -3 N-[1-(2-thienyl)ethyl]-2-(5-chlorothiophene)carbamide ■-4 N-[+ -(5-chloro-2-thienyl)ethyl]-
4-fluorobenzamide N-[1-(2-thienyl)ethyl]-3-isopropyloxybenzamide I-[3N-[1-(2-thienyl)ethylco 3,5-dimethylbenzamide pyrazole derivative (II) A preferred example is: 11-1 4(2,4-dichlorobenzoyl)-1,3-dimethylpyrazol-5-yl-paratoluenesulfonate 121 1,3-dimethyl-4-(2, 4-dichlorobenzoyl)-5-]phenacyloxypyrazole T-3 1,3-dimethyl-4-(2,4-dichloro-3-methylbenzoyl)-5-(4-methylphenacyloxy)
Pyrazole 1-methyl-4-(2,4-dichlorobenzoyl)-5
- Preferred examples of the benzyloxypyrazole cumylamide or cumylurea derivative (III) are as follows: N-(1,1-dimethylbenzyl)-2-bromothitope delacetamide I[r-2 1- (α, α-dimethylbenzyl)-3-(4-methylphenyl)urea Danji Main 1-(α, α-dimethylbenzyl)-3-(2-chlorobenzyl)urea In the present invention, N-[1 -(thienyl)edyl]amine derivative (I), pyrazole derivative (■), and cumylamide or cumylurea derivative <m> can be used as is, but it is usually used in solid or liquid form commonly used in the field of herbicides. It is used by mixing with a carrier or diluent and optionally an auxiliary agent, and formulating it by a conventional method.

The net type is similar to conventional herbicides, including granules, powders, wettable powders,
It may be either an emulsion or an aqueous suspension.

The weight ratio of the amine derivative (1), the pyrazole derivative (II), and the cumyl amide or cumyl urea derivative (III) is 30 to 300 g/10a of the amine derivative (1).

Pyrazole derivative (IF) h<90-300g/10
a.

30 cumylamide or cumylurea derivative (nl)
It is preferable to adjust the amount of application to 300 g/IOa.

The herbicidal composition of the present invention may contain a mixture of the amine derivative ([), pyrazole derivative (n) and cumylurea or cumylamide derivative (I [I)] in various amounts depending on the dosage form. can. For example, granules contain about 0.1 to 30% by weight of a derivative mixture as an active ingredient, and the derivative mixture is dispersed in a granular inert carrier, such as granular soil with a particle diameter of 0°2 to about 2 mm. , as appropriate.
It can be manufactured by adding a fixing agent etc. The powders contain from about 0.1 to about 20% by weight of a derivative mixture as active ingredient, a solid diluent such as diatomaceous earth, talc, mica, acid clay or quartz powder, and optionally auxiliaries. For example, it can be manufactured by finely pulverizing and mixing an oil absorbent, a lubricant, a stabilizer, or the like. Wettable powders contain about 10 to 80% by weight of a derivative mixture as an active ingredient, and must be thoroughly ground and mixed with the derivative mixture, solid diluent such as clay mineral, and surfactant such as nonionic surfactant. It can be manufactured by The emulsion contains about 5 to 80% by weight of the derivative mixture as an active ingredient, and can be prepared by mixing the derivative mixture, an organic solvent, and an emulsifier such as an anionic or nonionic surfactant. The aqueous suspension contains 5 to 70% by weight of the derivative mixture as an active ingredient, and can be produced by mixing the finely ground derivative mixture, water, and a wetting agent or dispersing agent. The herbicide composition of the present invention can be used with other herbicides, such as 4-(2
-methyl-4-chlorophenoxy)butanoic acid, 2-(2
, 4-dichloro-3-methylphenoxy)propionanilide and other phenoxy herbicides, 2°4-dichlorophenyl-4'-nitrophenyl ether, 2,4.6-dichlorophenyl-4'-nitrophenyl ether Diphenyl ether herbicides such as 2-chloro-4,6-pisethylamino-1,3,5-triazine: triazine-based such as 2-methylthio-4゜6-pisethylamino-1,3,5-triazine Herbicides, urea herbicides such as 3-(3,4-dichlorophenyl)-1,1-dimethylurea, methyl-2-[3-(4,6-cymethoxypyridin-2-yl)ureidosulfonylmethyl] Sulfonylurea herbicides such as benzoate, methyl-N-(3,4-
Carbamate herbicides such as dichlorophenyl) carbamate; thiocarbamate herbicides such as 5-(4-chlorobenzyl)-N,N-diethylthiol carbamate; S-ethyl-N,N-hexamethylenethiocarbamate; 3. 4-dichloropropionanilide; 2-chloro-
Acid amide herbicides such as 2°, 6°-diethyl-N-(butoxymethyl)-acetanilide, pyridinium herbicides such as 1,1°-dimethyl-4,4-bispyridinium chloride, N,N-bis Phosphorous herbicides such as (phosphonomethyl)-glycine, 5-(2-methyl-1-piperidylcarbonylmethyl)0.0-di-n-propyldithiophosphate, α,α,α-trifluoro-2,6-sinitro It is also possible to use it in combination with toluidine herbicides such as N,N-dipropyl-p-toluidine.

Furthermore, the herbicide composition of the present invention may optionally contain an insecticide,
Mixed use with nematicides, fungicides, plant growth regulators, fertilizers, etc. is also possible.

The herbicide composition of the present invention can be applied in the case of direct sowing by flooding, at the same time as the sowing, or 3 days to 14 days later, and in the case of transplanted cultivation, it can be applied at the same time as or 3 days before the weed growth period, for example. As a preparation (preferably granules) per 10 ares from before leaf emergence to the two-leaf stage of Japanese millet,
Excellent effects can be obtained when treated with 3 to 4 kg.

Next, examples will be shown to specifically explain the present invention.

Example 1 A 115,000 Ahl Wagner pot was filled with paddy soil (alluvial soil), watered and plowed, and test weed seeds and tubers were sown or transplanted to a water depth of 0.5 cm.
It was kept in a submerged state. One day later, 10 grains of Calper-coated paddy rice seeds coated with calcium peroxide (Culver) and 2.5 leaves of paddy rice variety "Nipponbare" were added to the pigeon stage paddy of the paddy rice variety "Nipponbare" that had been subjected to a water soaking treatment in advance. Seedlings 2
The books were sown and transplanted with one mallet into each pot at a depth of 1 cm and 2 CjI, respectively. Thereafter, the fields were watered to a depth of 3 cm, and after the field water became transparent, a predetermined amount of a diluted wettable powder of the test compound was dropped into each pot for treatment (weed pre-emergence treatment).

Next, test weeds were grown in a greenhouse for 14 days until the leaf age shown below using the same soil cultivation method, and a predetermined amount of a diluted solution of the test compound hydration powder was dropped into each pot to treat the weeds. growing season treatment)
.

Weed name Age Nobie 2L Broad leaf 2L Hotarui 2L Urikawa 2L Mizugaya Tsuri 1.5L Algae Frequency Frequent occurrence of duckweed Preparation and treatment of test compounds were performed as follows.

The test compound was formulated into a 25% hydrating powder (25% by weight of compound, 15% by weight of nonionic surfactant, 60% by weight of clay mineral), and then added to an amount of hydrating powder containing the amount of the test drug on each treatment day. water 1
The suspension was suspended at 0x12 and added dropwise to each pot using a pipette.

One day after the chemical treatment, water leakage was performed at 2 cx/day for 3 days.

During the test period, the water depth was always adjusted to a flooded state of 3 cx.

Observations were made every 7 days after compound treatment, and the results after 32 days are shown in Tables 1 and 2 below.

The herbicidal effect, the algicidal effect, and the chemical damage to paddy rice were visually observed, and each effect was evaluated on the following 6-grade scale from O to 5.

Herbicidal and algagicidal effects Chemical damage to paddy rice (versus untreated area) (versus manual weeding area) 5 Weed killing rate 90% or more Damage of 90% or more (almost complete death)
(almost complete death) 4 Weed killing rate 70-90% 70-
90% damage 3 Weed killing rate 40-70% 40-70% damage 2 Grade rate 20-40% 20-40% damage 1
Weed killing rate 5-20% Damage below 20% 0 Weed killing rate 5
% or less, almost no effect without drug damage) As a comparative example, pyrazole derivative (I[-1), cumylamide derivative (tII-1), and 2,4-bis(ethylamino)-6-methylthio-1,3,5 - The same test as in Example 1 was carried out using a mixture with triazine (simetrine). The results are shown in Tables 3 and 4.

Claims (1)

[Claims] 1. General formula: ▲ Numerical formula, chemical formula, table, etc. ▼ (I) [In the formula, Z is halogen, lower alkyl group or lower alkoxy group, n is 0, 1 or 2, R is ▲a mathematical formula, a chemical formula, a table, etc.▼ [However, X and Y are the same or different and are hydrogen, a linear or branched lower alkyl group (X and Y may form a ring) , a straight-chain or branched lower haloalkyl group, a straight-chain or branched lower alkoxy group, a straight-chain or branched lower alkoxymethyl group, or a halogen,
X and Y are not hydrogen at the same time. ), or ▲Mathematical formulas, chemical formulas, tables, etc.▼(However, Z and n
has the same meaning as above. ) represents. ] At least one type of N-[1-(thienyl)ethyl]amine derivative represented by , R^2 is a group represented by the formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ or ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (However, L is hydrogen or a methyl group.) Q is a group represented by , methyl group or chlorine k represents an integer of 0 to 3. ] At least one pyrazole derivative represented by the general formula: ▲Mathematical formula, chemical formula, table, etc.▼(III) There are chemical formulas, tables, etc. ▼ represents the group shown. ] A herbicidal composition containing at least one of cumylamide or cumylurea derivatives as an active ingredient.