FR2542974A1 - HERBICIDE COMPOSITION CONTAINING NITRODIPHENYL ETHER DERIVATIVE - Google Patents

Abstract

HERBICIDE COMPOSITION CONTAINING AS ACTIVE INGREDIENT A COMPONENT RESPONDING TO THE GENERAL FORMULA: (CF DRAWING IN BOPI) IN WHICH M DESIGNATES AN ALKALINE METAL. USED AS AN ACTIVE INGREDIENT IN THE PRESENT INVENTION, THIS COMPOUND MAY EXCEPT EXCELLENT WEED DESTRUCTION EFFECTS NOT ONLY IN PRE-EMERGENCY APPLICATIONS, BUT ALSO IN POST-EMERGENCY APPLICATIONS. THIS IS AN EXCELLENT HERBICIDE, IN PARTICULAR TAKING INTO ACCOUNT ITS EXTREMELY HIGH SAFETY TOWARDS OBTUS LEAF CROPS SUCH AS SOYBEAN AND ITS REMARKABLE DESTRUCTIVE EFFECTS ON WEEDS WHICH ARE LEAF LEAF GLOUTERON (XANTHIUM STRUMARUM) AND VOLUBILIS (IPOMEA PURPUREA), which are very harmful weeds.

Description

1.

Herbicide composition.

  The present invention relates to a composition

  herbicide containing a nitrodiphenyl ether.

  The effectiveness of diphenyl ethers as weed control agents is well known. However, it is extremely difficult even today to predict the effects of each diphenyl ether as a herbicide on the sole basis of its chemical structure. A group of diphenyl ethers, very close to each other in structure, often tend to have totally different herbicidal activities. Like their herbicidal activities, their phytotoxicity to crops tends to vary considerably for even a small difference in In addition, it has frequently been found that their degrees of tolerance vary greatly from one compound to another with a slightly different chemical structure in both

  pre-emergence only in post-emergence applications.

  Japanese Patent 64557/1980 discloses a compound having the following structural formula: ## STR1 ##

CF 3 QX N 02

  namely 2-chloro-4-trifluoromethylphenyl ether 3- / 2- (3-

  carboxypropionyl) -hydrazino / -4-nitrophenyl. The aforementioned patent indicates that the above compound

  has herbicidal effects when applied pre-

  emergence of soybeans and cotton, which are

  However, its herbicidal activity and the tolerance of

  res for this compound are still considered insufficient and its effectiveness is not satisfactory,

  particularly in post-emergence applications.

  One of the aims of the invention is to provide a novel herbicide having excellent herbicidal effects not only in pre-emergent applications, but also

  in post-emergence applications.

  The above object can be achieved by means of a herbicidal composition which contains as active ingredient a compound corresponding to the general formula (I) ## STR1 ##

CF 3 Q O NO 2 (I)

  wherein M is an alkali metal.

  The above compound, which is used as a

  active in the present invention, has been shown to be

  good tolerance, especially for stubby crops such as soybean, and has remarkable herbicidal effects on stubby weeds.

  The above compound, which is used as a

  Active ingredient in the present invention may be prepared in the following manner: a compound of the general formula (II) is first reacted;

CF 3 O 3 NO 2 (II)

  wherein X denotes a nitro group, a chlorine atom or ci with hydrazine, which provides in high yield a compound corresponding to the following formula (III) Ci NHNH 2

CF- O--

3 Q O Q -NO 2 (III)

  The compound of formula (III) above is then reacted with succinic anhydride

  presence of a dehydrating agent (for example pyridine

  ne) and a compound having the formula (IV) below is obtained easily and in high yield.

CF 3 -5 C> -NO 2 (IV)

  The alkali metal salt used as an active ingredient in the present invention can be prepared by reacting the compound of general formula (IV) with

  the desired metal-alkali hydroxide in an alcohol.

  The compound, which is used as active ingredient

  in the present invention is useful as a herbicide for

  cable, both before weeds appear and during their growth. It has remarkable effects, especially when applied during the

  Weed growth It is advantageous to apply

  the compound, which is used as an active ingredient in the present invention, to crops such as corn, cotton, soy beet, sunflower and

cereals.

  The compound, which is used as an active ingredient in the present invention, can be applied in any amount to achieve the necessary inhibition

  weed growth A normal rate of application

  of the compound of the invention is from 0.1 to 100 g per

  are of the active ingredient, preferably from 1 to 20 g per is.

  The compound of the invention may be applied either alone or in combination with a carrier and, if necessary, one or more other adjuvants, the resulting mixture being fed into a form of preparation commonly used in the art,

  for example in the form of powders, granules, powders

  Examples of carriers are mineral materials such as clay, talc, calcium carbonate, diatomaceous earth, zeolites, silicic anhydride, etc. organic materials of plant origin such as wheat flour, soy flour, starch, crystalline cellulose, etc .; high molecular weight materials such as petroleum resins, polyvinyl chloride, polyalkylene glycols, etc., urea; sayings; etc. Examples and liquid carriers include various oils, organic solvents

and water.

  Examples of adjuvants which can be used for wetting, dispersing, spreading, agglutination, stabilization of active ingredients, inhibition of rust, etc., include various surfactants, high molecular weight such as gelatin,

  albumin, sodium alginate, methylcellulose,

  carboxymethylcellulose, polyvinyl alcohol, etc. and

other adjuvants.

  Examples of surfactants that may be mentioned are nonionic surfactants such as those obtained by polymerizing ethylene oxide with alkyl phenols, higher alcohols, alkyl naphthols and fatty acids.

  fatty acid esters and dialkyl amines.

  phosphoric, and those prepared by copolymerizing ethylene oxide and propylene oxide; anionic surfactants such as salts of alkyl sulfuric esters, such as sodium lauryl sulphate, salts of alkyl sulphonates such as sodium 2-ethylhexene sulphonate, sodium lignosulphonate, aryl sulphonates such as sodium dodecylbenzene sulphonate ; cationic surfactants;

  and amphoteric surfactants.

  The supports and adjuvants described above can be used appropriately, alone or in combination,

  depending on the type of preparation and the conditions of application.

  The content of active ingredient is generally from 1 to 20% by weight in the powders, from 20 to 90% by weight in the wettable powders, from 1 to 30% by weight in the granules, from 5 to 80% by weight in the powders. soluble chemicals

  in water and from 5 to 30% by weight in aqueous solutions.

  When using the compound, ie the ingredient

  As an active herbicide, it can be formulated as a preparation with one or more other herbicides, agricultural chemicals such as insecticides, germicides, plant growth regulators, etc., soil conditioning materials. and fertilizers, not to mention the application of the active ingredient of the invention associated with these herbicides, agricultural chemicals, soil conditioners and / or fertilizers In some cases,

  expect some synergistic effects.

  As representative examples of herbicides used

  in combination with the compound, ie the ingredient

  active ingredient of the invention, there may be mentioned the compounds below.

  These examples are not limiting.

  Auxin Herbicides: 2,4-dichlorophenoxyacetic acid (including its esters and salts); 2-methyl-4-chlorophenoxy acetic acid (including its esters and salts); 4- (2,4-dichlorophenoxy) butyric acid (including its esters and salts); 3-amino-2,5-dichlorobenzoic acid; and

  4-chloro-2-oxobenzothiazolin-3-yl acetic acid -

  Triazine Herbicides 3-chloro-4,6-bis (ethylamino) -1,3,5triazine 2,4-bis (ethylamino) -6-methylthio-1,3,5-triazine 2-chloro-4-ethylamino-6-isopropylamino -1,3,5-triazine

  2-Ethylamino-4-isopropylamino-6-methylthio-1,3,5-

triazine; and

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

  Urea (3, 4-dichlorophenyl) -1,1-diethylurea 3 (3,4-dichlorophenyl) -1-methoxy-1-methylurea 1,1-dimethyl-3 (3-trifluoromethylphenyl) urea herbicides; 3 ', 4 - (4-chlorophenoxy) phenyl] -1,1-dimethylurea methylcyclohexyl) -3-phenylurea (4-chlorophenyl) -1-xethoxy-1-methylurea;

  3- (4-methoxyphenoxy) phenyl 7-1,1-dimethylurea.

  Herbicides of the anilide type 3 ', 4'-dichloro ropionanilide 2-methyl-4chlorophenoxyaceto-O-chloroanilide α-chloro-N-isopropylacetanilide-chloro4-methyl-2-propionanilido-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 2chloro-N-isopropylacetanilide. Herbicides of the type hydroxybenzonitrile 4hydroxy-3,5-iodobenzonitrile 3,5-dibromo-4-hydroxybenzonitrile; and

  4-hydroxy-3,5-iodobenzonitrile octanoate.

  Herbicides of the uracil type 3-tert-butyl-5-chloro-6-xethyluracil-bromo-3-sec-butyl-6-inethyluracil; and

  3-cyclohexyl-5,6-trimethylene uracil.

  2,4-Dichlorophenoxy-4'-nitrodiphenyl ether 2,4,6-trichlorophenoxy-4'-nitrodiphenyl ether diphenyl ether ether herbicides;

  2,4-dichlorophenoxy-3'-hexethoxy-4'-nitrodi-

  phenyl ether 2-nitro-4-trifluoromethyl-4'-nitrodiphenyl;

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

lic

  2-chloro-4-trifluoromethyl-3-i-methoxycarbonyl ether

  4'-nitrodiphenyl; and methyl <+) -2-14 <2,4-dichlorophenoxy> phenoxipropionate. Isopropyl-N- (3-chlorophenyl) -carbamate Isopropyl-N-phenylcarbamate Herbicides Methyl-N <3,4-dichlorophenyl) carbamate S-ethyldipropylthiocarbamate S-pchlorobenzyldiethylthiocarbamate Methyl-N (4-amino) -benzenesulfonyl) carbamate Ethy 11-N, N -di-n-propylthiolcarbamate 4-chlorobenzyl-N, N-diethylthiocarbamate; and Ethyl-N, N-hexamethylenethiolcarbamate. Herbicides of the aniline type 2, 6-dinitro-N, N-dipropyl-4-trifluoromethylamine N-butyl-N-ethyl-2,6-dinitro-4-trifluoromethylamine and

  3,4-dimethyl-2,6-din-itro-N-1-ethylpropylaniline.

  Herbicides of the pyridinium salt type 1,1'-dimethyl-4,4'-bis-pyridinium dichloride; and

  9,10-dihydroxy-8α, 10α-diazoniaphenyl dibromide

  throne. Other herbicides N, N-bis (phosphonomethyl) glycine;

  Oa O, ac-trifluoro-2,6-dinitro-N, N-dipropyl-p-

toluidine N-dipropyl-p-toluidine;

  S- (2-methyl-1-piperidinylcarbonylmethyl) -O, O-

dipropyl;

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

5-one;

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

phosphoroamidothioate;

  N- (O, -O-dipropyldithiophosphorylacétyl) -2-methyl-

  piperidine; 2,4-diamino-5-méthothio-6-chloropyrimidine; and

  2- (1-allyloxyaminobutylidene) -5,5-dimethyl-4-

  methoxycarbonylcyclohexan-1,3-dione (sodium salt).

  In the following examples, processes for the preparation of compounds, i.e., active ingredients of the invention, as well as methods for synthesizing and recovering the intermediate for the synthesis of these compounds will be described. Preparation Example 1 (reference): Synthesis of 2-chloro-4-trifluoromethylphenyl-3-hydrazino-4-nitrophenyl ether (intermediate) In 100 ml of dioxane, 105 g (0.3 μmol) are introduced

  2-chloro-4-trifluoromethylphenyl 3,4-dinitrophenyl ether

  45 g (0.9 mol) of hydrogen are then added dropwise.

  Hydrazine hydrate at a temperature below 30 ° C. The mixture obtained is then stirred for 5 hours at 40-50 ° C., thereby terminating the reaction. The reaction mixture is then left to stand overnight. The reaction mixture is poured into 500 ml of water. iced, which precipitates crystals, and 100 g of the desired product is obtained in raw form (yield: 95.9%) is recrystallized from 400 ml of ethanol, which provides 84 g of the desired product very pure (yield: 80.6%) Mp = 129-131 C. Elemental composition (%): Calculated for C 13 H 9 C 1 F 3 N 303: 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.

IR V K Br (cm-): max

3350 (NH).

  Preparation Example 2 (reference):

  Synthesis of the ether 2-chloro-4-trifluoromethylphenyl 3-

  2- (3-carboxypropionyl) -hydrazino-4-nitrophenyl

  In 50 ml of tetrahydrofuran, 7.0 g are dissolved

  (0.02 mole) 2-chloro-4-trifluoromethylphenyl 3-hydraether

  zino-4-nitrophenyl obtained in Preparative Example 1 and 2 ml of pyridine, to which 2.2 g (0.022 mole) is added

  of succinic anhydride with stirring at room temperature.

  The resulting mixture is then stirred at room temperature for 2 hours to terminate the reaction. The reaction liquid is concentrated under reduced pressure and the residue is poured into 100 ml of benzene. The resulting mixture is stirred for a short period of time, and thus obtained. 7.9 g of

  desired product (yield 88.3%) mp = 169-170.5 C.

Elemental Composition (%):

  Calculated: C, 45.59; H, 2.91; Cl, 7.93; F 12.74; N, 9.39.

  Found: C, 45.29; H, 2.59; C, 8.01; F 12.86; N, 9.40.

IR K Br (m -1 I Rv (cm-): max

3360 (NH) 1625, 1740 (C = O).

Preparation Example 3:

  Synthesis of the sodium salt of the ether 2-chloro-4-trifluoro-

  methylphenyl 3- [2- (3-carboxypropionyl) hydrazine]

  nitrophenyl (compound N 1) 44.8 g of ethyl alcohol are dissolved in 500 ml of ethyl alcohol

  (0.1 mole) 2-chloro-4-trifluoromethylphenyl 3- (2- (3-

  carboxypropionyl) -hydrazino-4-nitrophenyl obtained in Preparation Example 2, after which 42 g of a 10% aqueous solution of sodium hydroxide (0.1 mole of NaOH) were added dropwise. stirring at ambient temperature Then the resulting mixture is stirred at 40 ° C. for 1 hour to complete the formation of salt. Ethyl alcohol and water are removed under reduced pressure to obtain 46.9 g (the stoichiometric amount). ) of

  Desired Compound (Compound No. 1) Mp = 170-175C

  Elemental Composition (%): Calculated: C, 43.46; H, 2.58; Cl 7.55; F 12.13; N 8.95

  Found: C, 43.08; H, 2.76; C, 7.74; F 12.01; N, 8.73.

-1

IR v K Br (cm max

1675, 1625 (C = O).

Preparation Example 4:

  Synthesis of the potassium salt of 2-chloro-4- ether

  trifluoromethylphenyl 3- (2-carboxypropionyl) hydrazino

  4-nitrophenyl (Compound No. 2) Following the procedure of Preparation Example 3 except that 59 grams of aqueous solution of 10% aqueous potassium hydroxide (0.1 mole) were used. in KOH) instead of 42 g of the 10% aqueous sodium hydroxide solution, 48.6 g (the stoichiometric amount) of the desired compound (Compound No. 2) are obtained. Pf = 182-184 C Elemental Composition ( %)

  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 max

1670, 1630 (C = O)

  Examples of formulation of herbicidal compositions

  In the following formulation examples, compounds ## STR1 ## denote sodium and potassium salts, respectively, and all parts thereof.

are by weight.

  Formulation Example 1: 50 Parts of Compound No. 1, 40 Parts

  of diatomaceous earth and 10 parts of dodecylbenzenesulphonate

  Sodium fonate and ground. 100 parts of wettable powder are obtained. Formulation Example 2: 50 parts of compound 2, 40 parts of talc, 7 parts of sodium laurylphosphate and 3 parts of sodium alkylnaphthalenesulphonate are mixed together. 100 parts are obtained

of wettable powder.

  Formulation Example 3: 50 parts of compound n 2 and 50 parts of sodium alkylnaphthalenesulphonate are mixed and 100

  parts of a chemical soluble in water.

  Formulation Example 4 80 Parts of Compound No. 1, 10 Parts

  of sodium lignosulfonate and 10 parts of carboxymethyl

  cellulose to get 100 parts of a chemical

soluble in water.

  Formulation Example 5 20 parts of compound n 2, 5 parts of sodium dodecylbenzenesulphonate, 3 parts of polyvinyl alcohol and 72 parts of water are mixed to obtain 100 parts

an aqueous solution.

  Formulation Example 6: 15 Parts of Compound No. 1, 5 Parts

  of sodium alkylnaphthalenesulphonate, 2 parts of ligno

  sodium sulphonate, 3 parts of carboxymethylcellulose and 75 parts of water to obtain 100 parts of a solution

aqueous.

  Formulation Example 7: To 1 part of Compound No. 1, 5 parts of "white carbon", 5 parts of sodium dodecylbenzene sulfonate, 2 parts of carboxymethylcellulose and 87 parts of clay,

  water is added and then granulated to obtain 100 parts

Formula.

  Formulation Example 8: 2 parts of compound n 2, 2 parts of sodium alkylnaphthalenesulphonate and 96 parts of clay are mixed together

to obtain 100 parts of powder.

  Formulation Example 9: 20 parts of compound n 1, 1 part of nonylphenyl ether of polyethylene glycol, 2 parts of carboxymethylcellulose and 77 parts of water are mixed to obtain

parts of aqueous solution.

  Formulation Example 10: 20 parts of compound n 1, 1 part of polypropylene glycol polyethylene glycol ether, 2 parts of sodium lignosulfonate and 77 parts of water were mixed to obtain

parts of asante solution.

  Herbicidal activities and degrees of crop tolerance for the compounds, i.e. for the active ingredients of the invention, will now be described.

  in the following specific tests Compared to the

  active compounds of the invention, the control compound described in Japanese Patent No. 64557/1980 / the compound according to

  formula (IV), that is to say the ether T 2-chloro-4-trifluoro-

  methylphenyl 3- (2- (3-carboxypropionyl) hydrazinol) -4-

  nitrophenyl will be referred to as "Compound A" in the following tests / it was inferior as

  herbicide activity as crop tolerance.

  The effectiveness of the active ingredients of the invention is

  clearly, particularly in their applications in the post-

emergence.

  The active ingredients of the invention are salts

  of Control Compound A The conversion to salts

  The properties of the active ingredients of the invention which have various and unexpected characteristic effects have been modified. In summary, the transformation into salts has increased their solubility in water. Differences in the surface state of the leaves of each plant seem to have resulted in differences in biological effects: it seems that a greater quantity of compound adheres to the plants which tend to get wet with water. On the contrary, the quantity of adherent compound seems to decrease in the case of plants containing large quantities wax in their skin or whose leaves have hair on them

  surface, because the compound is easily transformed into a droplet

  flowing, and the leaves remain more difficult

to wet over their entire surface.

  However, the importance of the differences in activity between the active ingredients of the invention and Control Compound A are too great for the superiority of the active ingredients of the invention to be able to be attributed to Control Compound A above Let's look now

  the chemical structures of the active ingredients of the invention

  Each of the active ingredients of the invention has a large hydrophobic portion and a branched chain containing an aliphatic carboxylic acid at its furthest end. A conversion of the aliphatic carboxylic acid to salt thus appears to confer the properties of a kind. Thus, each of the active ingredients of the invention appears to act as a surfactant, thus being able to easily penetrate from the surface of each plant, resulting in anionic surfactants to each of the active ingredients of the invention. an increase in its activity In fact, the effect of each of

  active ingredients of the invention as a surfactant;

  active is easy to predict when measuring voltage

  superficial of an aqueous solution of the active ingredient.

  As shown in Table 1, they have values close to that of sodium dodecylbenzenesulphonate, which is an anionic surfactant.

  does not observe a significant difference in super-

  between Control Compound A, which is an acid, and

1 water.

  The effects of the active ingredients of the invention as surfactants are generally difficult to observe in their pre-emergence applications but

  Easily decline in their post-emergence applications.

  This difference can be attributed to the fact that they act

  mainly on the ground, in applications

  emergence, because of the presence of soil, while in

  post-emergence applications, they are made to act directly

  on plants Particularly high activities

  active ingredients of the invention in their applications.

  in post-emergence, compared to Control Compound A, appear to be evidence that the ingredients

  active agents of the invention are surfactants.

Table 1

  Compound Concentration No. 1 No. 50 ppm 58 T 7,500 ppm 42.2 A -soluble solution 722 saturated surfactant 50 ppm 54.1 active X 500 ppm 33.0 water 73.0 * sodium dodecylbenzenesulphonate Test 1;

  Herbicide power test with post-application

  Each time 450 g of air-dried mountain soil is placed in a resin jar of λ / 10,000, after which the entire layers of the soil thus potted are smoked with a chemical fertilizer containing 100 mg of water. N, P 205 and K 20, respectively Plant seeds of a test plant are planted in the soil and allowed to germinate and grow in a greenhouse When the test plants have reached their 2-3 leaf stage, spraying thereon, using a micropulverizer, a test compound The test compound is formulated as a wettable powder according to the procedure of the example of formula 2 and the prescribed amount of the wettable powder is diluted using a volume of water equivalent to 10 1 per 30 days after the application of the test chemical, the growth state of the plants is studied. The results of the study are given in Table 2. expressed by the following quotation, based on the weight of deadline to air

  plants in an untreated plot.

  Air-dried weight of plants compared with plants C o t t i o N in an untreated plot

O 76 100

1 51 75

2 36 50

3 I 35

426 10

5

Table 2

  Weeds Dig-S * Ech-C * Ama-R * Che-A * 4 5s

5 5

5 5

5 5

2 2

4 4

4 4

5

Xan S * -

* 5

5

5

5

  * Abbreviations: Dig-S = Digitaria sanguinalis; Echo C Crops Soybeans Cotton Tournesc LI Beetroot, Sugar Y o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o i o o o o o o o F-, = Echinochloa crus-galli; = Amaranthus retroflexus; Che-A = Chenopodium album; = Xanthium strumnarium; i = active ingredient Compo s No i No 2 Rate g i a / a * i i A i Ama-R Xan-S n. Test 2 Field test with soybean On 11 April 1982, 160 kg / 10 ares of magnesium lime were introduced into the soil with a disc plow or harrow at a depth of 20 cm. May 18, using a chemical fertilizer containing NP 205 and K 20 in the ratio of 3: 7: 10 We broadcast broadcast 90 kg / 10 ares of fertilizer We planted soybeans and weeds May 24 Soybeans were planted with a row spacing of 60 cm and spacing within rows of 15 cm The soybean was of the species "Hakucho Edamame" Each plot was 3 mx 5 m and the The experimental field was located in Chigasaki, Kanagawa, Japan. On June 17, each of the test compounds was applied using an ordinary herbicide sprayer using a wettable powder obtained by formulating the compound of the test compound. according to the procedure of the example of formulation 1 and diluting the prescribed amount of the wettable powder with a volume of water equivalent to 5 liters per year A month later the growth status of both the crop and the weed was examined. The study is summarized in Table 3. They were evaluated on a scale of 11 in which 10 = complete death of the plant and 0 = none = activity and the results were averaged separately.

for each parcel.

  Table 4 gives the results of a test carried out almost simultaneously near Sendai, Miyagi,

  Japan, following the test procedures of Table 3.

Table 3

  Rate g i a / a * Biological activity Set-V * Che-A * Xan-S * Ipo-P * Abu-T * Dat-S * Soya i 8 10 10 10 10

* 3 9 10 10 10 10

A 2 0 O 6 e 3 7 5,3 8 01,8

0, 5 0.5 8 7 8 7.15 8 1

  * Abbreviation: Set-V = Setaria viridis; Che-A = Chenopodium album; Xan-S = Xanthium strurnarium; Ipo-P = Ipomoea purpurea; Abu-T = Abutilon theophrasti; Dat-S = Datura stramoruium i.a = itl r eididnt ac tif g i a / a

Table 4 * C

  Bioloyic Activity Dig-S Set-V Xan-S Ipo-P 'sj

3 10 10 O

6 6, P 5 10 10 O

0, 5 O

2 1, y 3, 5 6 d, 3 7 1, i 13

8, 3 1,? 5

  Compose, No. 1 Compound No. 1 A Ln J-ru% 01 -J 1 -r- As shown in Tests 1 and 2, the compounds

  of the invention, namely the active ingredients of the invention.

  tion, have extremely high levels of tolerance for soybeans and have strong herbicidal activities against glouteron (Xanthium Struntari Xum), volubilis (Ipomea purpurea), etc. which are very harmful to soybeans. They have relatively weak herbicidal activities. grass grasses such as Digitaria Sanguinalis, Echinochloa crus-galli and Setaria viridis But there are already several techniques for the destruction of these grass grasses Needless to say, it is usually very difficult to control weeds with obtuse leaves in obtuse leafy crops and to control grass grasses in grass crops because of the properties of herbicides. But this is a sought after characteristic of herbicides. From this point of view, the compounds of the invention, that is, the active ingredients of the invention can be considered as herbicides satisfying the requirements most important in the sense that they have been found to have high tolerance levels for obtuse leaf crops such as soybean and have destructive effects

  remarkable on weeds with obtuse leaves.

Claims (4)

  A herbicidal composition containing as active ingredient a compound of the general formula: O C 1 NHNHCCH 2 CH 2 COOM CF 3 O NO   wherein M is an alkali metal.   2 herbicidal composition according to claim 1,   characterized in that the herbicidal composition is   blighted crops.   3 Herbicidal composition according to any one of   of claims 1 or 2, characterized in that the   Herbicide composition is suitable for post-application emergence to cultures.   4 A method of controlling harmful weeds, characterized in that a compound having the general formula Ci NHNHCCH 2 CH 2 COOM is applied CF 3 _-O_ _NO 2   wherein M denotes an alkali metal for an application   early post-emergence or post-emergence   culturing from 0.1 to 100 g of active ingredient per is.   Process according to Claim 4, characterized   in that the crop is a crop with obtuse leaves.