JPS6064903A - Herbicide composition - Google Patents

Abstract

PURPOSE:To provide a mixed herbicide composition having remarkable synergistic effect, and capable of killing various harmful weeds at a low rate of application, by using a specific pyrazole derivative in combination with a herbicide for paddy field selected from diphenyl ether-type herbicide, acid anilide- type herbicide, etc. CONSTITUTION:The objective composition contains, as active components, (A) the compound of formula (A is lower alkylene; X is halogen, NO2 or lower alkyl; n is 0-5) and (B) a compound selected from 32 kinds of known herbicides for paddy field, such as (i) S-(4-chlorobenzyl)-N,N-diethylthiol carbamate, etc. effective to cockspur-grass, (ii) 2,4,6-trichlorophenyl-4'-nitrophenol, etc. effective to cockspur-grass and broad-leaved annual weeds, (iii) 2-chloro-2',6'-diethyl- N-(butoxymethyl)acetanilide, etc. effective to Deccan grass, bulrush, water plantain, etc.

Description

Detailed Description of the Invention The present invention is based on the general formula [1]: (wherein A is a lower alkylene group, X is a halogen atom,
It represents a nitro group or a lower alkyl group, and n represents an integer of 1 to 5. When n is 2 to 5, X may be the same or different from each other. ) and a compound selected from the following compounds (1) to (2) as active ingredients.

Q) 8-(4-chlorobenzyl)-N,N-diethylthiol carbamate.

■ S-ethyl-hexahydro(1,8)azepine-1
- Carbothioate.

■ 5-1-ethyl-propyl-hexahydro (1H)
Azepine-1-carbothioate.

■ 4-Ethoxymethoxybenz-7,3'-dichloroanilide.

■ 2.4.6-) +7 Chlorpheny-4'-nitrophenol.

■ 2,4-dichlorophenyl-37-medoxy 4'
- Nitrophenyl ether.

■ 2.4-dichlorophenyl-3'-methoxycarbonyl-41-nitrophenyl ether.

■ Methyl-2-[2-chloro-5-(2,4-dichlorophenoxy)-7enoxy]propionate.

■ Inpropi, z-5-[2-chloro-4-(trifluoromethyl)-phenoxy]-2-nitropenzoate.

[Phase] 6-[2-nitro-5-(2-chloro-4-toI-nofluoromethylphenoxy)-phenoxy-tetrahydrofuran.

@3'-dimethyl-4-methoxy-benzophenone.

o 2-chloro-2',6'-diethyl-N-(butoxy/methyl)a-toanilide.

[Phase] 2-Cucoru 2/, 61-diethyl-N-(
Propoxyethyl)acetanilide.

(2) 2-chloro-2',6'-diethyl-N-(ethoxycarbonylmethyl)-acetanilide.

[Phase] 1-(α,α-dimethylbenzyl)-3-(4
-methylphenyl)-urea.

■ N-(α,α-dimethylbenzyl)-α-bromo tertiary-butyl-acetamide.

■ N-(α,α-dimethylbenzyl)-o-chlorophenylacetamide.

[Phase] Benzthiazol-2-yl-oxy-acetic acid-
N-methylanilide.

0 α-(β-su7toxy)propionanilide.

[Phase] 0,0-di-n-propyl-6-(2-methylpiperidin-1-yl-carbonylmethyl)-phosphorodithioate.

■ 0,0-dimethyl-8-[(N-i-propyl-N
-p-chlorophenyl)-lupamoylmethyl]-phosphorodithioate.

@0.0-diisopropyl-8-(2-benzenesulfonylaminoethyl)-phosphorodithioate.

■ 0.0-diphenyl-8-(2-methylpiperidin-1-yl-carbonylmethyl)-phosphorodithioate.

4-(2,4-dichlorobenzoyl) -1,5-
Dimethylpyrazol-5-yl-4-toluenesulfonate.

[Phase] 4-(2,4-dichlorobenzoyl) -1,
5-dimethyl-5-phenacyloxy-pyrazole.

[Phase] 2-Methylthio-4,6-bis(rethylamino)-8-)riazine.

(2) 2-Methylthio-4-C1,2-dimethylpropylamino)-6-nitylamino-S-)riazine.

■ 3-Isopropyl-1 day-2,1,3-benzothiadiazine-(4)-AH-one-2,2-dioxide.

■ 3-chloro-2-amino-1,4-naphthoquinone.

■ Ethyl 2-methyl-4-chlorophenoxyacetate.

■ Ethyl α-(2-methyl-4-chlorophenoxy)butyrate.

02-Methyl-4-chlorophenoxyacetic acid-8-ethyl ester.

That is, by blending a compound selected from the pyrazole derivatives represented by the above general formula [■] with a compound selected from the above compounds ■ or compound ■, a synergistic effect that is so remarkable that it cannot be expected from the single application of each is brought about. This invention relates to a mixed herbicide composition that is capable of killing many types of problem weeds at low application rates.

Currently, many herbicides have been put into practical use as herbicides for paddy fields, and are widely used as single agents or mixtures. However, there are many types of paddy weeds,
Although there are many herbicides that are effective against young weeds, there are very few herbicides that are sufficiently effective against perennial weeds over a wide range of grass species. For this reason, various types of perennial weeds are increasing, and there is a strong need for their control.

Perennial weeds generally grow vigorously, have a long emergence period, and are a type of harmful grass. Therefore, herbicides are desired to have a broad spectrum of herbicidal properties that can kill many types of weeds.

In addition, in recent years, mechanization and earlier transplantation of rice cultivation have rapidly become widespread, providing a more suitable place for weeds to grow than ever before, and complete weed control can be expected with -1 herbicide application. tend to be unable to do so. For this reason, the same or different herbicides are used several times, but repeated use of such herbicides not only requires a great deal of effort, but also causes undesirable problems such as chemical damage to paddy rice and residue in the soil due to large amounts of herbicides being applied. is being raised.

In order to improve these problems of conventional herbicides, the present inventors aimed to completely control all weeds using a one-time cloth, which is highly safe for paddy rice, and extremely toxic to humans and animals. As a result of continuing to search for a safe herbicide with a low herbicide, it was discovered that an excellent herbicide that solved these problems could be obtained by combining two types of active ingredients, and the present invention was completed.

That is, 2. the present invention provides a herbicidal mixture of a compound selected from the above-mentioned compounds known as herbicides for paddy fields, and a compound selected from the novel pyrazole derivatives represented by the general formula m. It is a drug.

To explain the present invention in more detail, Compound ■, Compound ■, Compound ■, Compound ■, Compound ■, Compound @, Compound @, Compound ■, and Compound ■, which are one of the ingredients of the two herbicides, It is highly effective, has high selectivity between rice and wild plants, and is highly safe for rice. In addition, compound ■, compound ■, and compound ■ have become problems in recent years.
It is also active against firefly and other insects that grow during early stages of growth, but as growth progresses, the effectiveness decreases markedly.

Next, compound ■, compound C), compound (I), compound ■
, Compound (1) and Compound (2) are so-called diphenyl ether herbicides, and are highly effective against wild grass and young broad-leaved weeds. It is also somewhat active against hotarui and urikawa in the early stages of growth, but once the growth progresses, it hardly shows any effective effect.

Compound [phase], compound ■, compound oi'i, and c anilide-based herbicides are highly effective against barnyard grass, firefly, young broad-leaved weeds, and grasshoppers, and are also effective against perennial water holly when treated in the early stages of growth. However, it is not sufficient.

Compound [Phase], Compound (1), and Compound (2) are generally somewhat less effective against barnyard grass, and some have relatively high efficacy against firefly and water snail, but their efficacy cannot be said to be sufficient for practical use.

Compound [phase], adduct@, compound and compound are:
Although it is classified as a photosynthesis-inhibiting herbicide due to its so-called mechanism of action, it generally has extremely low effects on barnyard grass and Cyperaceae.

However, the compound @ has high activity specifically against Cyperaceae and Cyperaceae. Also, compound [phase], compound [phase], compound ■, and adduct [phase].

It is an auxin type herbicide with plant hormone action.
It is highly effective against young broad-leaved weeds and perennial broad-leaved weeds such as snail grass, but it is less effective against barnyard grass, firefly, and cypress.

Compound ■, Compound ■, and Compound [Phase] are herbicides that have a bleaching effect that causes the plants to completely whiten and die, but the effectiveness of all of them against barnyard grass and water snails decreases as the plants grow older. do. Furthermore, the effect of compound (1) on perennial broad-leaved weeds such as Hatsu 11 Kawa is also insufficient.

On the other hand, the compound represented by the general formula [l-] exhibits high activity against barnyard grass, firefly, Japanese grasshopper, -young broad-leaved weeds, urikawa, Japanese cypress, and black porgy. It has extremely high activity against weeds of the Cyperaceae family, and also shows strong activity against barnyard grass in the early stages of growth.

The present inventors have proposed a compound represented by the general formula [1], a compound (1), a compound (2), a compound (2), a compound (2), a compound [phase]
, discovered that by applying a mixture of Compound [Phase], Compound ■, Compound 2, or Compound 0, it not only shows additive efficacy but also has a high synergistic effect on barnyard grass during the growing season. Furthermore, it was found that it has a wide herbicidal effect on weeds other than barnyard grass. Furthermore, the general formula [■]
It has been found that the compound represented by the formula (2), compound (2), compound (), compound (2), or compound O can be mixed and applied to show a high synergistic effect on barnyard grass during the growing season, and −Young broadleaf weeds, firefly,
It was found that it is also highly effective against prickly pear.

Also, compound ■, compound ■, or compound [phase].

By mixing and applying the compound represented by the general formula [1], it not only shows a high synergistic effect on barnyard grass, but also shows a high effect on firefly, water snail, etc. I found it.

Mano, monster ■, chemical substance ■ or compound ■.

It has been found that by mixing and applying the compound with the compound represented by the general formula [1], a high synergistic effect is exhibited against barnyard grass, firefly, and cypress.

It has also been found that the application of a mixture of Compound @, Compound O, Compound [Phase] or Compound ■ with the compound represented by the general formula [I] shows a high synergistic effect on barnyard grass. Furthermore, it has been revealed that it has a highly synergistic effect on young broadleaf plants, firefly, etc.

All examples of compounds having the general formula m' that are used as one of the active ingredients in the herbicide of the present invention are shown in Table 1 (compound numbers are referred to in the following description).

Incidentally, these compounds can be produced by the same method as in the examples described in Japanese Patent Application No. 57-69551 previously filed by the present applicant.

Table 1 The mixture shown in the present invention is a novel combination that has not been described in any literature, and of course, there is no literature that mentions its unique potency enhancement. The mutual effect related to the present invention is observed in a wide range of mixing ratios, and the compound represented by the general formula [1] is mixed in a ratio of 0.1 to 20 parts by weight per 1 part by weight of compound ■ or compound ■. They can be mixed to create useful herbicides.

The herbicide of the present invention thus completed is effective even when treated before and after the germination of weeds, and is highly effective when treated in soil or in combination with violet leaves and soil. Applications include not only paddy rice but also various grains, legumes, cotton,
Vegetables, orchards, lawns, pastures, tea gardens, forest lands, non-agricultural fields
[Useful on land, etc.]

The mixture of the present invention may be sprayed with the EC itself, or
Mixed with a carrier and other adjuvants as necessary, it can be used in formulations commonly used as herbicides, such as powders, coarse powders, fine granules, wettable powders, emulsions, aqueous solutions, aqueous solutions, and oil suspensions. It is prepared and used as a clouding agent.

5. When applying the active ingredient compound of the present invention as a herbicide, a suitable carrier, feed clay, talc, or bentonite is generally used.

Solid carriers such as diatomaceous earth or water, alcohols (methanol, ethanol, etc.), aromatic hydrocarbons, ethers, ketones, esters (ethyl acetate, etc.), acid amides (dimethylformamide, etc.), etc. It can be applied by mixing with a liquid carrier, and if desired, an emulsifier (1) may be added with a dispersant, a suspending agent, a penetrating agent, a spreading agent, a stabilizer, etc. It can be put to practical use in dosage form.

Further, if necessary, it may be applied in combination with other herbicides, various insecticides, fungicides, synergists, etc. at the time of formulation or spraying.

Next, a specific example of distribution of a preparation when using the adjunct of the present invention will be shown. Parts indicate parts by weight. However, the formulation examples of the present invention are not limited to these only.

Distribution Example 1 Granules After uniformly mixing and pulverizing the above ingredients, a small amount of water was added, the mixture was stirred and kneaded, and the mixture was granulated using an extrusion type granulator.

Dry and make into granules.

Formulation Example 2 Granules After uniformly mixing and pulverizing the above ingredients, a small amount of water is added, the mixture is stirred and kneaded, and the mixture is granulated using an extrusion granulator and dried to form granules.

Formulation Example 3 Granules After uniformly mixing and pulverizing the above ingredients, a small amount of water is added, the mixture is stirred and kneaded, and the mixture is granulated using an extrusion granulator and dried to form granules.

Formulation Example 4 Granules After uniformly mixing and pulverizing the above ingredients, a small amount of water is added, the mixture is stirred and kneaded, and the mixture is granulated using an extrusion granulator and dried to form granules.

Distribution Example 5 Granules After uniformly mixing and pulverizing the above ingredients, add a small amount of water, stir and knead, granulate using an extrusion granulator, and dry to form granules.

Distribution Example 6 Granules After uniformly mixing and pulverizing the above ingredients, a small amount of water is added, the mixture is stirred and kneaded, and the mixture is granulated using an extrusion granulator and dried to form granules.

Formulation Example 7 Granules After uniformly mixing and pulverizing the above ingredients, add a small amount of water, stir and knead, granulate with extrusion granulation (・j>, and dry to form granules.

Distribution Example 8 Granules After uniformly mixing and pulverizing the above ingredients, add a small amount of water, stir and knead, granulate using an extrusion granulator, and dry to form granules.

Formulation Example 9 Granules After uniformly mixing and pulverizing the above ingredients, a small amount of water is added, the mixture is stirred and kneaded, and the mixture is granulated using an extrusion granulator and dried to form granules.

Formulation Example 10 Granules After uniformly mixing and pulverizing the above ingredients, a small amount of water is added, the mixture is stirred and kneaded, and the mixture is granulated using an extrusion type granulator and dried to form granules.

Formulation Example 11 Granules After uniformly mixing and pulverizing the above ingredients, a small amount of water is added, the mixture is stirred and kneaded, and the mixture is granulated using an extrusion granulator and dried to form granules.

After uniformly mixing and pulverizing the above, a small amount of water is added, the mixture is stirred and kneaded, and the mixture is granulated using an extrusion granulator and dried to form granules.

Distribution Example 13 Granules After uniformly mixing and crushing the above ingredients, add a small amount of water, mix and knead with stirring, granulate using an extrusion granulator, and dry to form granules.

After uniformly mixing and pulverizing the above, a small amount of water is added, the mixture is stirred and kneaded, and the mixture is granulated using an extrusion type granulator and dried to form granules.

After uniformly mixing and pulverizing the above, a small amount of water is added, the mixture is stirred and kneaded, and the mixture is granulated using an extrusion type granulator and dried to form granules.

Distribution Example 16 Granules After uniformly mixing and pulverizing the above ingredients, add a small amount of water, stir and knead, and granulate with an extrusion granulator (2) Dry to form granules.

Formulation Example 17 Granules After uniformly mixing and pulverizing the above ingredients, a small amount of water was added, the mixture was stirred and kneaded, and the mixture was granulated using an extrusion type granulator.

Dry and make into granules.

Distribution Example 1B Emulsion Distribution Example 20 Emulsion (White Carbon; Shionogi & Co., Ltd.'s music product name) The above ingredients are mixed and pulverized uniformly to make an irrigation agent.

Test Example 1 Weeding effect test under flooded conditions 115000
After putting alluvial soil in Earl's Hugner pot,
Water was added and mixed to create a submerged condition of water depth 2.

Japanese millet, broad-leaved weeds (Japanese cabbage, Japanese azalea, Japanese grass)
, seeds of each kind of firefly were mixedly sown in the above pots,
In addition, we placed beds of Urikara tubers, Mizugaya Tsurugi tubers, and Kurogwai tubers. Furthermore, rice seedlings at the 2.5-leaf stage are transplanted, the pots are placed in a greenhouse at 20-25°C, the plants are grown, and on the 7th day after sowing, when the barnyard grass is at the 1-leaf stage, a predetermined amount of the chemical is administered. The diluted drug solution was added dropwise using a measuring pipette so that the results were as follows.

Five weeks after dropping the chemical solution, the herbicidal effect on various weeds was investigated according to the following criteria.

The results are shown in Table 2.

Judgment Criterion 5: Weed killing rate 90X or higher (almost complete death) 4.
・・ 1 70～90. ￥ 3...l 40-70X 2...1 20-4ON 1...I 5-20% 0...1 5% or less (hardly effective) However, the above weed killing rate is The above-ground flower weight of the chemical-treated plot and the above-ground fresh plant weight of the non-treated plot were measured and determined using the following formula.

Test Example 2 A polyethylene pot with an inner diameter of Bcrn was filled with paddy soil, and Japanese millet was grown in the paddy field, and the flooded soil was treated with each prescribed bone drug formulated as an irrigation agent for two leaves of barnyard millet M.

The pots were placed in a greenhouse at 25 to 30°C for controlled cultivation, and 30 days after the treatment, the weight of the remaining above-ground grass of barnyard grass and the weight of the above-ground grass in the untreated area was measured, and the following results were obtained. The herbicidal capacity (96'l) was calculated using the formula.

The results are shown in Table 3.

Explanation of the E value in Table 3.Individual activated additives often have their own drawbacks in their herbicidal activity, but in that case, the total combination of the two types of activated additives When the herbicidal activity is greater than the simple sum (expected activity) of the respective activities of the two compounds, this is called synergism.

The expected activity of a specific combination of two herbicides is 1.
The kill can be calculated as follows (colby,
S, Ft, calculation of synergistic and antagonistic reactions of herbicide combinations (see Weed J vol, 15.20-22 Negative, 1967): Inhibition rate Y: Herbicide!'l'i) Inhibition rate E when treated at the amount of M/R: Expected when herbicide A is used at/R and herbicide B at bF/R, i.e. If the actual inhibition rate is greater than the E value calculated above, it can be said that the two combinations of activities exhibit synergistic effects.

Patent applicant Nissan Chemical Industries, Ltd. Continued from page 1 ■Int, C1,' Identification symbol Internal adjustment) Procedures Supplement
Author: Kazuo Wakasugi, Director General of the Patent Office, 1. Indication of the case: 1982 Patent Application No. 175076 Z Name of the invention: Herbicide composition! Relationship with the L amendment person case Patent applicant address 14-5-7 Kanda Nishiki-cho, Chiyoda-ku, Tokyo 101;
Contents of the date amendment of the amendment order (1) As per the appended claims (2) “[Phase]” stated in the fifth line from the bottom of page 7 of the specification
N-(α,α-dimethylbenzyl)” wo[(i→N-(
α′, α′-dimethylbenzyl)”.

(3) Insert the following information between the 6th and 7th lines of the bottom of page 53 of the specification.

"-ρ℃" target compound [D... 4 parts compound [phase] 4 parts bentonite
・・・・・・・・・・・・ 37 parts talc ・・・・・・・・・5
After 5 parts or more were uniformly mixed and pulverized, a small amount of water was added, stirred, mixed, kneaded, and granulated using an extrusion granulator.

Dry and make into granules.

Formulation example 24 Granule compound [4] ... ... 3 part compound
qφ ・・・・・・・・・ 3 parts bentonite ・・・
・・・・・・ Part 48 ・ ・ ・ ・ ・
・ ・ ・ After uniformly mixing and pulverizing 46 parts or more,
Add a small amount of water, stir, mix, knead, and granulate using an extrusion granulator.

Dry and make into granules.

(4) In the compound point column of the table on page 41 of the specification ([1
) +Q) and ([1] +<i extract), insert the following items.

[(Attachment) Z Claims (1) General formula [■]: (In the formula, A represents a lower alkylene group kn xi; t represents a halogen atom, a nitro group, or a lower alkyl group; +n+
'jO or an integer from 1 to 5.

When n is 2 to 5, X may be the same or different from each other. A herbicidal composition containing as active ingredients a compound selected from the pyrazole derivatives represented by ) and a compound selected from Compound 1 to Compound @ of F.

■ 5-(4-chlorobenzyl)-N,N-diethylthiol carbamate.

■ 8-ethyl-hexahydro (1 day) azepine-1-
Carbothioate.

+, a) 5-1-ethyl-propyl-hexahydride o (
1 [()Azepine-1-carbothioate.

■ 4-Ethoxymethoxy7benz-2',3'-dichloroanilide.

(M) 2,4,6-dolychlorophenylated-4'-nitrophenol.

■ 2.4-dichlorophenyl-"-meth)ki7-zm=
Trophenyl ether.

(2) 2,4-dichlorophenyl-3'-methoxycarbonyl-47-nitrophenyl ether.

(limethyl-2-[2-chloro-5-(2,4-dichlorophenoxy)-7enoxy]propionate.

■ Inglovir-5-[2-chloro-4-(trifluoromethyl)-phenoxy]-2-nitrope/shade.

(Jφ 3-[2-nitro-5-(2-chloro-4-)
1j Fluoromethylphenoxy)-7dinokykutetrahydrofuran.

(Φ He3'-dimethyl-4-methoxy7-penzophenone.

@2-chloro-2',6'-diethyl-N-(butoxymethyl)acetanilide.

[Phase] 2-chloro-2'16'-diethyl-N-(probox-7ethyl)acetanilide.

02-chloro-2',6'-diethyl-N-(ethoxycarbonylmethyl)-acetanilide.

[Phase] 1-(α,α-dimethylbenzyl)-3-(4
-methylphenyl)-urea.

[Phase] N-(α', α'-dimethylbenzyl)-α-
Promoter Shary-butyl-acetamide.

ON-(α,α-dimethylbenzyl)-〇-chlorophenylacetamide.

[Phase] Benzthiazol-2-yl-oxy-acetic acid-
N-methylanilide.

0 α-(β-su7toxy)propionanilide.

[Phase] α0-di-n-propyl-8-(2-methylpiperidin-1-yl-carbonylmethyl)-phosphorodithioate.

◎ [LO-dimethyl-6-[:(l-1-propyl-n-p-chlorophenyl)-carno(moyl-methyl]-phosphorodithioate.

OQO-diisopropyl-8-(2-benzenesulfonylaminoethyl)-phosphorodithioate.

[Phase] O-diphenyl-S-(2-methylpiperidin-1-yl-carbonylmethyl)-phosphorodithioate.

■ 4- (2,4-dichlorobenzoyl)-1,5-
Dimethylpyrazol-5-yl-4-toluenesulfonate.

[Phase] 4-(2,4-dichlorobenzoyl)-1,6
-Simethyl-5-7enafluoxy-pyrazole.

[Phase] 2-Methylthio-4,6-bis(ethylamino)-S-triazine.

02-Methylthio-4-(1,2-dimethylpropylapino)-6-e, thylamino-S-triazine.

03-Inglovir-11(-2,1,3-indithiadiazine-(4)-5I(-one-λ2-dioxide.

[Phase] 3-chloro-2-amino-1,4-nuttoquinone.

Ethyl 02-methyl-4-chlorophenoxyacetate.

■ Ethyl α-(2-methyl-4-chlorophenoxy) Nishikata.

02-Methyl-4-chlorophenoxyacetic acid-S-ethyl ester.

”

Claims (1)

[Claims] (In the formula, A represents a lower alkylene group t, X represents a) rogene atom, nitro group, or lower alkyl group, and n represents 0 or an integer of 1 to 5. When n is 2 to 5, they may be the same or different from each other. ) and a compound selected from the following compounds (1) to (2) as active ingredients. ■ 5-(4-chlorobenzyl)-N,N-diethylthiolcano(mate. ■ Day-ethyl-hexahydro(1H) azepi/-1-
Carbothioate. ■ 5-1-ethyl-propyl-hexahydro (1B)
Azepine-1-carbothioate. 04-Ethoxymethoxybenz-2',5'-dichloroanilide. ■ 2,4.6-)dichlorophenylnitro-nitrophenol. ■ 2.4-dichlorophenyl-6'-methoxy-4'
- Nitrophenyl ether. ■ λ4-Dichlorophenyl-3'-methoxycarbonyl-4'-nitrophenyl ether. ■ Methyl-2-[2-chloro-5-(2,4-dichlorophenoxy)-phenoxy]propionate. ■ Isopropyl-5-[2-chloro-4-(trifluoromethyl)-7enoxy]-2-nitrobe/shade. [Phase] 3-[2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)-phenoxy-tetrahydrofuran. ■ 3.5'-dimethyl-4-methoxy-benzophenone. (2) 2-chloro-2',6'-diethyl-N-(butoxymethyl)acetanilide. 02-Chloro-7,6'-diethyl-N-(propoxyethyl)acetanilide. 02-chloro-2',6'-diethyl-N-(ethoxycarbonylmethyl)-acetanilide. [Phase] 1-(α, α-dimethyl be/zyl)-3-(4
-methylphenyl)-urea. ON-(α,α-dimethylbenzyl)-α-promoter shari-butyl-acetamide. ■ N-(α,α-dimethylbenzyl)-〇-chlorophenylacetamide. ■ Benzthiazol-2-yl-oxy-acetic acid-N-
Methylanilide. [Phase] α-(β-7toxy)propionanilide. @l to 0-di-n-propyl-8-(2-methylpiperidin-1-yl-carbonylmethyl)-phosphorodithioate. O020-dimethyl-day-((N-i-propyl-N-
p-chlorophenyl)-carbamoylmethyl]-phosphorodithioate. @0,0-diisopropyl-8-(2-benzenesulfonylaminoethyl)-phosphorodithioate. ■ [1LO-diphenyl-8-(2-methylpiperidin-1-yl-carbonylmethyl)-phosphorodithioate. [Phase] 4-(2,4-dichlorobenzoyl) -1,
3-dimethylpyrazol-5-yl-4-toluenesulfonate. [Phase] 4-(2,4-dichlorobenzoyl) -1,
5-dimethyl-5-7 enacyloxypyrazole. [Phase] 2-Methylthio-4,6-bis(ethylamine)-8-)riazine. o 2-Methylthio-4-(1,2-dimethylpropylamino)-6-nitylamino-S-) riazine. 03'-isopropyl-I H-2,1,5-benzothiadiazine-(4)-5H-one-2,2-dioxide. 03-Chloro-2-amino-1,4-naphthoquinone. ■ Ethyl 2-methyl-4-chlorophenoxyacetate. ■ Ethyl za-(2-methyl-4-chlorophenoxy)butyrate. ■ 2-Methyl-4-chlorophenoxyacetic acid-ethyl ester.