DE3309141A1 - HERBICIDAL COMPOSITION - Google Patents

Description

Herbicidal Composition

The invention relates to a herbicidal composition which contains a nitrodiphenyl ether derivative.

The effectiveness of diphenyl ether derivatives as herbicides is well known. However, even now it is extremely difficult to determine the effects of the individual diphenyl ether derivatives as a herbicide can only be predicted on the basis of its chemical structure. One learned that a group of diphenyl ether derivatives which are structurally very similar to one another often tend to exert completely different herbicidal effects. Similar to their weed control properties, theirs tends to Crop phytotoxicity to this, to a considerable extent, even with a slight difference in to vary the chemical structures. Furthermore, their tolerance levels have often been found to be up to to a noticeable extent from one connection to another-

-He , which has only a slightly different chemical structure from the former compound, vary, both in pre-emergence treatments and in post-emergence treatments.

In Japanese Patent Laid-Open No. 64557/1980 describes a compound which has the following structural formula owns:

O Il

Cl / NHNHCCh ₂ CH ₂ COOH

CF ₃

namely 2-chloro-4-trifluoromethylphenyl-3- (2- (3 ~ carboxy ~ propionyl) hydrazine) -4-nitrophenyl ether. From this patent publication it appears ^ that the aforementioned compound has weed control effects in its pre-emergence treatments in soybeans and cotton, which are Oberland crops. Their herbicidal effects and However, tolerance to harvested material is still regarded as insufficient and their effectiveness is not satisfactory-ε-sharing, especially in their post-emergence applications.

An object of the invention is to provide a new herbicide create excellent weed control effects not only in pre-emergence applications but also in post-emergence applications running applications can develop.

This object is achieved by providing a herbicidal composition that acts as an active ingredient contains a compound represented by the following general formula:

0
NHNHCCtI ₂ CH ₂ COOM (D

wherein M denotes an alkali metal.

It has been found that this compound can be used as an active ingredient in the present invention has good tolerance, especially for broad-leaved crops such as soybeans, and is excellent Shows control effects against broad-leaved weeds.

The following is a preferred embodiment of the Invention described in more detail.

The above-mentioned compound used as an active ingredient in the present invention can be made in the following manner. A compound represented by the following general formula (II) is shown:

Cl

where X is a nitro group, a chlorine atom or - 0 - m,

is first reacted with hydrazine to obtain a compound with a high yield, which is represented by the following formula (III):

-G-

NfINH _{2 (III)}

Thereafter, the compound of the given formula (III) is treated with succinic anhydride in the presence of a dehydrating agent (e.g. pyridine) reacted so that a compound is obtained easily and in a high yield which is represented by the following formula (IV):

O Il Cl, NHNHCCH ₅ CIi ₅ COOH (IV)

^CF 3 "\ 2 /" ° V ^ / ~

The alkali metal salt that acts as an active ingredient used in the present invention can be made by implementing the connection established by the general Formula (IV) shown is made with the hydroxide of a desired alkali metal in an alcohol will.

The compound used as an active ingredient in the present invention is as a Herbicide useful both prior to the appearance of weeds and during the growth of weeds is applicable. It shows excellent effects, especially when used in the growing season of weeds is applied. It is advantageous to use the compound which is used as an active ingredient in the present

the invention is used on crops such as corn, cotton, soybeans, sugar beet (Beta vulgaris L. var.altissima Doell), sunflowers and cereals apply.

The compound described in the present invention as an active ingredient can be used in any An amount that provides the necessary inhibition for weed growth to be applied. One Standard rate for the application of the compound of this invention is in the range of 0.1 to 100 grams of des

active ingredient per are (100m), with a preferred application rate in the range of 1 to 20 grams per Ar of the active ingredient of this invention.

The compound of this invention can be used either neat or by combination with a carrier and, if it is is necessary, one or more additives or adjuvants and by shaping the resulting Mixture in a preparation form as it is usually used, e.g. as dust or Dusts, granular formulations, wettable powders, emulsifiable concentrates, water-soluble chemicals, aqueous solutions and the like. As examples of supports, there can be mentioned inorganic materials such as Clay, alumina, talc, potassium carbonate, diatomaceous earth, zeolite, silicon dioxide and the like; organic materials of vegetable origin such as wheat flour, soybean flour, starch, crystalline cellulose, etc .; high molecular weight Materials such as petroleum resins, polyvinyl chloride, polyalkylene glycols, and the like; Urea; Waxes etc. On the other hand, examples of liquid carriers include a variety of oils, organic solvents and Water.

As an example of a device or adjuvant that can be used for the Purposes of wetting, dispersion, spreading, adhesion, stabilization of active ingredients, rust inhibition and the like can be used, can use various surfactants, high molecular compounds such as gelatin, albumin, sodium alginate, Methyl cellulose, carboxymethyl cellulose, polyvinyl alcohol and the like and other adjuvant agents can be mentioned.

As examples of surface active agents, there can be mentioned non-ionic surfactants such as those obtained by polymerizing ethylene oxide with alkyl phenols, higher alcohols, alkylnaphthols, higher fatty acids, Fatty acid esters and dialkylphosphoric acid amines, and those obtained by copolymerizing are made of ethylene oxide and propylene oxide; anionic surfactants such as salts of alkyl sulfuric acid esters, e.g. sodium lauryl sulfate, salts of alkyl sulfonates, e.g. sodium 2-ethylhexene sulfonate, Sodium lignosulfonate, aryl sulfonates, e.g., sodium dodecylbenzenesulfonate; cationic surfactants and ampho-ionic surfactants.

The carriers and excipients or adjuvant means described above can be appropriately used, either alone or in combination, according to the Type of each preparation and the conditions of each application.

The content of the active ingredient can generally be from 1 to 20% by weight in dusts, from 20 to 90% by weight in wettable powders, from 1 to 30% by weight in granular ones Formulations, from 5 to 80% by weight in water-soluble chemicals and from 5 to 30% by weight in aqueous solutions are sufficient.

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When the compound / i.e. the active ingredient is used as a herbicide, it can be used together with a or more other herbicides, agricultural chemicals such as insecticides, germicidal plant growth regulators and the like, soil conditioning materials and fertilizer materials are formulated into preparations because nothing against the use of the active ingredient of this invention in combination with such herbicides, agricultural chemicals, soil conditioning materials and / or fertilizer materials speaks. In some cases, certain synergistic effects can be expected.

Typical examples of herbicides used in combination with the compound, i.e. the active ingredient of the invention, may include the following compounds. It is noted, however, that such Herbicides are not limited to this.

Auxln-type herbicides

2,4-dichlorophenoxyacetic acid (including its esters and salts);

2-methyl-4-chlorophenoxyacetic acid (including its esters and salts);

4- (2,4-dichlorophenoxy) butyric acid (including their esters and salts);

3-amino-2,5-dichlorobenzoic acid and 4-chloro-2-oxobenzothiazolin-3-y! -Acetic acid

-Ιο-

Triazln-type herbicides:

3-chloro-4 _/ 6-bis (ethylamino) -1,3,5-triazine; 2,4-bis (ethylamino) -6-methylthio-1,3,5-triazine; 2-chloro-4-ethylamino-6-isopropylamino-1,3,5-triazine;

2-Xthylamino-4-isopropy] amino-6-methylthio-1 / 3,5-triazine and

2-chloro-4-diethylainino-6-ethylamino-1,3,5-triazine.

Kamstoff-type herbicides:

3- (3,4-dichlorophenyl) -1,1-diethylurea; 3- (3,4-dichlorophenyl) -1-methoxy-1-methylurea; 1,1-dimethyl-3- (3-trifluoromethylphenyl) urea; 1- (2-methylcyclohexyl) -3-phenylurea; 3- (4-chlorophenyl) -1-methoxy-1-methylurea;

3- (4- (4-chlorophenoxy) phenyl) -1,1 -dime thy! Urea and

3- (4- (4-Meth oxyphenoxy) phenyl) -1,1-dimethylurea,

Acid anilide type herbicides:

3 '^' - dichloropropionanilide;
2-methyl-4-chlorophenoxyaceto-0-chloroanilide; oC-chloro-N-isopropyl acetanilide; 5-chloro-4-ynethyl-2-propionanilide-1,3-thiazole; 2-chloro- (2 ', 6'-dinitroanilino) -N-methylpropionamide; 2-chloro-2 ', 6-diethyl-N- (butoxymethyl) acetanilide; 2-chloro-2 ', 6'-diethyl-N- (propoxyethyl) acetanilide and

2-chloro-N-isopropyl acetanilide.

Hydroxybenzonitrile-type herbicides:

4-hydroxy-3,5-iodobenzonitrile; 3,5-dibromo-4-hydroxybenzonitrile and 4-hydroxy-3,5-iodobenzonitrile octanoate.

Uracil-type herbicides:

S-tert-butyl-S-chloro-e-methyluracil; S-bromo-S-sec-butyl-e-methyluracil and -S, 6-trimethyleneuracil.

Diphenyl ether type herbicides ;

2,4-dichlorophenoxy-4'-nitrodiphenyl ether; 2,4,6-trichlorophenoxy-4 · nitrodiphenyl ether;

2,4-dichlorophenoxy-3'-methoxy-4'-nitrodiphenyl ether; 2-nitro-4-trifluoromethyl-4'-nitrodiphenyl ether?

2-chloro-4-trifluoromethyl-4'-nitrodiphenyl ether;

2-chloro-4-trifluoromethyl-3'-methoxycarbonyl-4'-nitrodiphenyl ether and

Methyl (-) - 2- (4- (2,4-dichlorophenoxy) phenoxy) propionate,

Carbamate-type herbicides:

Isopropyl N-phenyl carbainate; Isopropyl N- (3-chlorophenyl) carbamate; Methyl N- (3,4-dichlorophenyl) carbamate; S-ethyl dipropyl thiocarbamate;

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S-p-chlorobenzyl diethyl thiocarbamate; Methyl N- (4-amino) benzenesulfonyl) carbamate; Xthyl N / N-di-n-propyl thiol carbamate; 4-chlorobenzyl-N, N-diethylthiocarbamate and Ethyl N, N-hexamethylene thiol carbamate.

Aniline-type herbicides:

2,6-dinitro-N / N-dipropyl-4-trifluoromethylamine;

N-butyl-N-ethyl-2,6-dinitro-4-trifluoromethylamine

and

3,4-dimethyl-2,6-dinitro-N-1-ethylpropylaniline.

Pyridinium salt type herbicides;

1,1'-dimethyl ~ 4,4'-bispyridinium dichloride and

9,10-dihydroxy-ea, 10a-diazoniaphenanthrone dibromide.

Other herbicides:

N, N-bis (phosphonome thy1) glyein;

OC, OC, <* - trifluor-2, e-dinitro-NfN-dipropyl-p-toluidine;

N-dipropy1-p-toluidine;

S- (2-methyl-i-piperidinylcarbonylmethyl) -0,0-dipropyl phosphorodithioate;

4-amino-6-tert-butyl-3-methylthio-1 , 2 , 4-triazin-S-one;

O-ethyl 0- (2-nitro-5-methylphenyl) -N-sec-butyl phosphoramidothioate;

N- (O / O-dipropyldithiophosphorylacetyl) -2-methylpiperidine;

2, ^ Diamino-S-methothio-e-chlorpyriinidin and

2- (1-Allyloxyaminobutylideno) -5,5-dimethyl-4-methoxycarbonylcyclohexane-1,3-dione (Sodium salt).

The following examples illustrate preparation procedures for compounds which form the active ingredients of this invention, and synthesis and recovery methods for intermediates for the synthesis of such compounds.

Preparation example 1 (reference):

Synthesis of 2-chloro-4-trifluoromethylphenyl-3-hydrazine-4-nitrophenyl ether (Intermediate).

105 g (0.3 mol) of 2-chloro-4-trifluoromethylphenyl-3,4-dinitrophenyl ether were taken up in 100 ml of dioxane, followed by the dropwise addition of 45 g (0.9 mol) of hydrazine hydrate at temperatures below 30.degree . Thereafter, the resulting mixture was stirred at 40 to 50 ° C for 5 hours to thereby complete the reaction. The reaction mixture was then left to stand overnight. The liquid reaction mixture was poured into 500 ml of ice water to precipitate crystals, whereby 100 g of the desired product were obtained in a crude form (yield: 95.9%). It was recrystallized from 400 ml of ethanol, which gave 84 g of the desired product with high purity (yield: 80.6%), melting point 129 to 131 ^° C.

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Elemental analysis data (%):

Calculated for C ₁₃ H ₉ ClF ₃ N ₃ O ₃ : C, 44.89; H 2.59; Cl 10.22; F 16.40; N 12.09.

Found: C, 44.78; H 2.41; Cl 10.12; F 16.51; N 12.14,

3350 (NH)

Manufacturing example .2. (Reference).:

Synthesis of 2-chloro-4-trifluoromethylphenyl 3- (2 - '(3-carboxypropionyl) -hydrazine) -4-nitrophenyl ether (intermediate).

In 50 ml of tetrahydrofuran, 7.0 g (0.02 mol) of the 2-chloro-4-trifluoro obtained in Preparation Example 1 were added methylphenyl 3-hydrazine-4-nitrophenyl ether and 2 ml of pyridine dissolved, including 2.2 g (0.022 mol) of succinic anhydride under Stirring at room temperature was added. Then, the resulting mixture was kept at room temperature for 2 hours stirred long to complete the reaction. The liquid reaction mixture was concentrated at negative pressure, and the residue was poured into 100 ml of benzene. The resulting mixture was stirred for a while, whereby 7.9 g of the intended product were obtained (yield: 88.3%), melting point 169 to 170.5 ° C.

Elemental analysis data (%):

Calculated: C 45.59; H 2.91? Cl 7.93; F 12.74; N 9.39. Found: C, 45.29; H 2.59; Cl 8.01; F 12.86; N 9.40.

IR v ^KBr (cm " ¹ ):

* Max '

3360 (NH). 1625, 1740 (C = O). Manufacturing example 1 3:

Synthesis of the sodium salt of 2-chloro-4-trifluoromethylpheny1 3- (2- (3-carboxypropionyl) hydrazine) -4-nitrophenyl ether (Compound no.1)

44.8 g (0.1 mol) of the 2-chloro-4-trifluoromethylphenyl obtained in Preparation Example 2 were added to 500 ml of ethyl alcohol 3- (2- (3-carboxypropionyl) hydrazine) -4-nitrophenyl ether dissolved, followed by a dropwise addition of 42 g a 10% aqueous solution of sodium hydroxide (0.1 mol as NaOH) with stirring at room temperature. Thereafter the resulting solution was stirred at 40 ° C. for 1 hour to complete the salt formation. Ethyl alcohol and water were stripped off under reduced pressure, yielding 46.9 g (the stoichiometric amount) of the desired compound (Compound No. 1), melting point 170 to 175 ° C.

Elemental analysis data (%):

Calculated: C, 43.46; H 2.58; Cl 7.55; F 12.13; N 8.95, Found: C, 43.08; H 2.76; Cl 7.74; F 12.01; N 8.73.

1675, 1625 (C = O).

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- 14 Production example 4:

Synthesis of the potassium salt of 2-chloro-4-trifluoromethylphenyl 3- (2- (3-carboxypropionyl) hydrazine) 4-nitrophenyl ether (Compound No. 2).

Following the procedure of Preparation Example 3, but using 59 g of a 10% aqueous solution of potassium hydroxide (0.1 mole as KOH) was used in place of 42 g of the 10% aqueous solution of sodium hydroxide were obtained, 48.6 g (the stoichiometric amount) of the desired compound (Compound No. 2) was obtained. Melting point 182-184 ° C.

Elemental analysis data (%):

Calculated: C, 42.02; H 2.49; Cl 7.30; F 11.73; N, 8.65. Found: C, 42.33; H 2.53; Cl 7.08; F 11.65; N 8.27.

^IR '»

1670, 1630 (C = O).

The following are examples of formulations of the herbicidal compositions of this invention. In the following formulation examples, compound no. 1 the sodium salt and compound no. 2 that Potassium salt and all terms of "part" or "parts" mean part by weight and parts by weight, respectively.

Formulation example 1

Fifty parts of compound No. 1.40 parts of diatomaceous earth and 10 parts of sodium dodecylbenzenesulfonate were oe-

-η -

mixed and ground to 100 parts of a wettable powder. Formulation example 2

Fifty parts of compound No. 2, 40 parts of talc, 7 parts of sodium lauryl phosphate, and 3 parts of sodium alkylnaphthalenesulfonate were mixed to 100 parts netzbarem powder.

Formulation example 3

Fifty parts of compound No. 2 and 50 parts sodium alkyl naphthalene sulfonate were mixed into 100 parts of a water-soluble chemical.

Formulation example 4

Eighty parts of compound No. 1, 10 parts of sodium lignosulfonate and 10 parts of carboxymethyl cellulose became 100 parts of a water-soluble chemical together combined.

Formulation example 5

Twenty parts of compound No. 2.5 parts sodium dodecylbenzenesulfonate, 3 parts of polyvinyl alcohol and 72 parts of water were combined to 100 parts of an aqueous Mixed solution.

Formulation example 6

Fifteen parts of compound No. 1.5 parts of sodium alkylnaphthalene sulfonate, 2 parts of sodium lignosulfonate, 3 parts of carboxymethyl cellulose and 75 parts of water were combined mixed to 100 parts of an aqueous solution.

-η ■

Formulation in.spie.1 7

Part of compound no. 1, 5 parts white carbon black, 5 parts Sodium dodecylbenzenesulfonate, 2 parts carboxymethyl cellulose and 87 parts of alumina were combined with water and then granulated into 100 parts of a formulation.

Formulation example 8

Two parts of compound no. 2, 2 parts of sodium alkylnaphthalenesulfonate, 96 parts of clay were mixed together to 100 parts of dust.

Formulation in.sp.iel 9

Twenty parts of compound No. 1, 1 part polyethylene glycol nonylphenyl ether, 2 parts of carboxymethyl cellulose and 77 parts of water became 100 parts of one together mixed aqueous solution,

Formulation example. 10

Twenty parts of compound No. 1, 1 part polypropylene glycol polyethylene glycol ether, 2 parts of sodium lignosulfonate and 77 parts of water were combined into 100 parts of a mixed aqueous solution.

Next, the herbicidal effects and crop tolerance levels of the compounds, i. of the active ingredients of this invention are described in the following specific tests. Compared to the active ingredients of this invention was the control compound disclosed in Japanese Patent Laid-Open No. 64557/1980 is described (the connection

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of formula (IV) i.e. 2-chloro-4-trifluoromethylphenyl 3- (2- (3-carboxypropionyl) hydrazine) -4-nitrophenyl ether, which is referred to herein as Compound A in the following tests), inferior both in terms of herbicidal Effect as well as on the crop tolerance. The effectiveness of the active ingredients of this invention was evident especially in their post-emergence applications.

The active ingredients of this invention are salts of control compound A. Conversion to salts is attributable to that the active ingredients of this invention have changed markedly in their properties, whereby they show characteristic effects that vary far beyond expectations. Simply put, the conversion to salts has increased their solubility in water. Differences in leaf surface conditions the individual plants seem to have produced differences in their biological effects. There seems to be more of the compound attached to the plants, which have a tendency to get wetted with water. In contrast, the amount of compound adhered seems to decrease when the plants are in larger amounts Contain wax on their surfaces or skins, or have a number of hairs on their leaf surfaces, because the compound is easily formed into drops and so can run off and the leaves heavier on the entire surface are wetted.

The extent of the differences in the effects of the active ingredients of this invention and the control compound However, A are too great to show the superiority of the active ingredients of this invention over the control compound A would be affected for this reason. Considerations will now be given of the chemical structures of the active ingredients of this invention.

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Each of the active ingredients of this invention has a large hydrophobic portion and a branched chain, which contains an aliphatic carboxylic acid at its distal end. That is why there seems to be a conversion of the aliphatic Carboxylic acid in a salt the individual active ingredients of this invention properties of a species of anionic surfactants. This is why every one of the active ingredients appears to be this Invention to serve as a surfactant and in this way is able to easily through the To penetrate the surfaces of the individual plants, which leads to increased effects. Indeed you can the effect of the respective active ingredients of this invention as a surface active agent easily imagine when measuring the surface tension of an aqueous solution of the active ingredient. As in Table 1, they have values close to those of sodium dodecylbenzenesulfonate, which is an anionic surfactant. On the other hand, there is no noticeable difference in surface tension observed between Control Compound A, which is an acid, and water.

The effects of the active ingredients of this invention as surfactants are generally with theirs However, pre-emergence applications can become difficult to perceive easily show in their post-emergence applications. This Difference can be attributed to the fact that they basically act on the ground at pre-emergence uses due to the presence of the soil, while being able to act directly on plants at Post-emergence applications. The particularly superior effects of the active ingredients of this invention in their post-emergence applications as compared to the control compound A seem to be evidence of the fact that the

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active ingredients of this invention surface-active Means are.

Table 1

link concentration Surface chip
tion
(dyn / 17 ° C) No. 1 50 ppm
500 ppm 58.7
42.2 A. Saturated aqueous
solution 72.2 Surface ac
tive mean +) 50 ppm
500 ppm 54.1
33.0 water - 73.0

+) Sodium dodecylbenzenesulfonate.

Test 1

Post-emergence herbicide test.

450 grams of air-dried upper field soil was added to each resin-made pot of a / 10000, after which was followed by fertilization of the whole layers of the so potted soil with a chemical fertilizer, respectively 100 mg of N, P ₂ O 5 ^{and K} 2 ° ^entnielt · seeds of a Test plants were planted in the ground, and then germinated and grown in a greenhouse. When the test plants had reached their 2-3 leaf stage, they were sprayed using a micro-spray device with a test method

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bond sprayed. The test compound was in a wettable state
Powder was formulated according to the procedure of Formulation Example 2, and a certain amount of the wettable powder was diluted using a volume of water equivalent to 10 liters per are. Thirty days after the application of the test chemical, the state of growth of the plants was examined. Test results are given in Table 2. Be it
noted that the investigations were conducted according to the following ranking, which is based on the
air-dry weight of plants in an untreated test area is based.

Ranking Air-dry weight of

Plants compared to that of plants in untreated Area(%).

0 76-100

51 - 75 36 - 50 11 - 35 6 - 10 0 - 5

Rate, DIg-S ⁺ ECh-C ⁺ r 5 Xan-S * soy Crop to sunbathe crus-galli? sugar ι
1 CO g a.B./a 5 beans. tree flower . beets $ Uo CO Connect 4th 4th Table 2 5 5 0 wool . 0 0 I, OD manure 1 5 5 5 5 0 0 0 0 2 5 5 Weeds 5 5 0 0 1 0 - * 5 5 5 Ama-R Che-A 5 5 0 1 1 1 No. 1 10 4th 4th 5 5 0 1 0 0 1 5 5 5 5 5 0 0 0 0 2 5 5 5 3 5 0 0 1 0 5 5 5 5 4th 5 0 1 1 1 No. 2 10 2 2 5 5 2 0 1 0 0 1 4th 4th 5 5 3 0 0 1 0 2 4th 4th 5 = Digitaria sanguinalis; Ech-C 4th 0 0 2 1 t, ι 5 5 5 5 5 1 1 2 2 A. 10 5 = Echinochloa 2 t J · I Abbreviations: Dig-S 3 ¹ ! 4th ι> ■ 5 5

Ama-R = Amaranthus retroflexus? Che-A = Chenopodium album; Xan-S = Xanthium strumarium; away. = active component.

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Test 2:

Field trial for soybeans

On April 11, 1982, 160 kg / 10 ares of magnesium lime was plowed or harrowed into the ground to a depth of 20 cm. Fertilization was carried out on May 18 using a chemical fertilizer containing N, P ₂ ⁰ B ^and K ₂ O in a ratio of 3: 7: 10. 90 kg / 10 ares of the fertilizer was scattered. Soybean seeds and weed were brought in on May 24th. Soybean plants had a row spacing of 60 cm and a spacing within the row of 15 cm »

The type of soybean was "Hakucho Edamame". Each area was 3 m × 5 m and the test was carried out on four replicas. The test field was in Chigasaki, Kanagawa, Japan. On June 17, each test compound was applied by means of a standard herbicide sprayer / using wettable powder obtained by formulating the test compound according to the method of Formulation Example 1 and diluting a certain amount of the wettable powder with a volume of water which 5 liters per ar was equivalent. A month later, the condition of the growth of each crop and the weed was examined. The test results are compiled in Table 3. The test results were rated on a scale of 11, where 10 = total plant death and 0 = no effect, and the results for each patch were averaged separately.

Table 4 shows results of a test conducted near Sendai, Miyagi, Japan around the same time was. The test procedures in Table 3 were followed.

Table 3.

Connect Rate ₊ set-v * Che-A ⁺ Biological effect . Dat-S ⁺ . . Soybean <*>
CO manure g a.B "/ ä XcUi-S ⁺ XpO-P ⁺ . . AbU-T ⁺ O
CO

- 2 1 8 10 1O 10 10 O

5 3 9 10 10 10 10 O

1 8th 10 1O 10 3 9 10 10 10 O O 6.3 7th 5.3 0.5 0.5 8th 7.8 7.5

2 5 3 10 10 0 5 6th 6.5 10 10 0 2 0.5 0 3.5 7th 1.3 5 2 1.5 6.3 8.3 1.5

_A 2 0 0 6.3 7 5.3 8 0.8

5 0.5 0.5 8 7.8 7.5 8 1

Abbreviation: Set-V = Setaria viridis; Che-A = Chenopodium album; /

Xan-S = Xanthium strumarium; Ipo-P = Ipomoea purpurea; ta

Abu-T = Abutilon theophrasti; Dat-S = Datura stramonium 'ι

away. = active component

Table 4

Connect rate ./a Dig-S Set-V. Organic activity manure gave Xan-S. Ipo-P. Soybean

As shown in Tests 1 and 2, the compounds have of this invention, i.e., the active ingredients of this invention, extremely high levels of tolerance against soybeans and show high herbicidal effects against grain wheels (Xanthium strumarium), bindweed, purple bindweed (Ipomoea purpurea) and the like, which are very harmful to the soybean. You pretty own weak herbicidal effects against grassy grasses such as Digitaria sanguinalis, Echinochloa crusgalli and Setaria viridis. However, there are already various methods of controlling such grassy ones Grasses known or been carried out. Needless to say, in general it is extreme it is difficult to control broad-leaved weeds in the cultivation of broad-leaved crops and control grassy grasses in the cultivation of grassy crops, which is based on the properties of the Herbicide based. However, this is obviously a characteristic of herbicides, according to which is most sought. From this point of view, the compounds of this invention, i.e. the active ingredients of this invention, as herbicides, meet this most important requirement because they have been found to have high levels of tolerance for broad-leaved crops such as soybeans have and show excellent control effects against broad-leaved weeds.

It is clear to the person skilled in the art that the examples given above only illustrate the invention and offer wide variations and permit modification without departing from the spirit of the invention.

Claims (1)

Applicant:, MITSUI TOATSU CHEMICALS, INCORPORATED No. 2-5, Kasumigaseki 3-chome, Chiyoda-ku,
Tokyo, Japan P a ten tan.spr.tic.he Herbicidal composition, thereby characterized as having a compound as an active ingredient which is represented by the following general formula: Il NHNHCCH ₂ CH ₂ COOm where M denotes an alkali metal. Herbicidal composition according to claim 1, characterized in that that the herbicidal composition can be used in broad-leaved crop plants. Herbicidal composition according to claim 1 or 2, characterized in that that the herbicidal composition for post-emergence applications Crop plants is suitable. Method for combating harmful weeds, characterized that a compound represented by the following general formula: Il NHNHCCH CH COOM , where M denotes an alkali metal, for early post-emergence or "pre-emergence" application to a crop in an amount of 0.1 to 100 grams per ar (100 m ² ) as
is turned. (100 m) as an active component 5. The method according to claim 4, d a you r c h characterized in that the The crop is a broad-leaved crop plant.