DE3601148A1 - N- (3-SUBST.-4-ISOPROPYLPHENYL) -2-METHYL-2-PENTENAMIDE DERIVATIVE AND SELECTIVE HERBICIDE - Google Patents

Description

N- (3-substituted-4-isopropylphenyl) -2-methyl-2-pentenamide derivative and selective herbicide

description

The invention relates to an N- (3-substituted-4-isopropylphenyl) -2-methyl-2-pentenamide derivative and a selective herbicide containing this as an active ingredient, the harmful weeds in cultivation of wheat, an important grass crop in agriculture, effectively and selectively by application fights the foliage.

For the control of weeds in the cultivation of wheat, phenoxy type herbicides have been widely used. They include, for example, 2,4-dichlorophenoxyacetic acid [2,4-D; P. ¥. Zimmerman and AEHitchcock, Contrib. Boyce Thompson Inst., _12, 321 (1942)], 2-methyl-4-chlorophenoxyacetic acid [MCPA; MESynerholm and PWZimmerman, Contrib. Boyce Thompson Inst., 14 , 91 (1945)], 4- (2-methyl-4-chlorophenoxy) butyric acid [MCPB; DE-PS 1 000 632 (1957) and GB-PS 793 513 (1958)] and 4- (2,4-dichlorophenoxy) butyric acid [2,4-DB; ME Synerholm and PW Zimmerman, Contrib. Boyce Thompson Inst., 1-4, 369 (1945)]. However, these herbicides are foliar treatment agents which are only effective in controlling broadleaf weeds, and because of their significant phytotoxicity to wheat, their use is limited to only a stage where the crop has grown to some extent.

Urea-type herbicides such as 3- (3,4-dichlorophenyl) -1-methoxy-1-methy! Urea [Linuron; U.S. Patent 2,960,534, Issued November 15, 1960], 3- (3-chloro-4-methoxyphenyl) -1,1-dimethylurea [Metoxuron; FR-PSen

1,497,867 and 1,497,868, issued October 13, 1967], 3- (3-chloro-4-methylophenyl) -1,1-dimethylurea [Chlortoluron; U.S. Patents 2,655,444 and 2,655,445 issued to U.S. Pat

October 13, 1953], 3- (4-Isopropylphenyl) -1,1-dimethylurea [Isoproturon; DE-OS 2 107 774 published on September 16, 1971, and DE-OS 2,137,992, published February 10, 1972] and 3- (2-benzothiazolyl) -1,3-dimethylurea [Methabenzthiazuron; U.S. PS

2 756 135 of July 24, 1956 and GB-PS 1 085 430 of October 4, 1967], are very important in wheat breeding. However, since most of them have phytotoxicity of the fruit, they are mainly used as pre-emergent soil treatment agents. When used as a foliar treatment agent, their selectivity differs greatly, depending on the variety of wheat, the cultivation conditions, etc. Furthermore, their herbicidal spectrum does not cover all incidental weeds wheat cultivation and they are commonly used as mixtures.

Attempts have been made to obtain 2- (2-chloro-4-ethylamino-s-triazin-6-yl-amino) -2-methyl oropionitrile [Cyanazine; GB-PS 1 132 306, pat. October 30, 1968], 3,4-dimethyl-2,6-dinitro-N- (1 -ethylpropyl) aniline [pendimethalin; de-OS 2 232 263, published. January 11, 1973J α, α, α-trifluoro-2,6-dinitro-N- (2-chloroethyl) -N-propyl-ptoluidine [Fluchloralin; DE-OS 2 161 879, published. June 20, 1973] and 2,4-dichlorophenyl-3-methoxycarbonyl-4-nitrophenyl ether [Bifenox; U.S. Patent No. 3,784,635 issued Jan. 8, 1974] as herbicides for controlling weeds

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of wheat cultivation. They are also used as mixtures, and when used alone they show insufficient effectiveness against many dangerous weeds.

4-chloro-2-butynyl-N- (3-chlorophenyl) carbamate (Barban; U.S. Patent 2,906,614, September 29, 1959), N-Benzoyl-N- (3,4-dichlorophenyl) -2-aminopropionic acid, ethyl ester (Benzoylprop-ethyl; NL application 6 717 715 from July 1st 1963), 1,2-dimethyl-3,5-diphenyl-1H-pyrazolium methyl sulfate (Difenzoquat; DE-OS 2 441 504, published March 20, 1975) and methyl (+) - 2- [4- (2,4-dichlorophenoxy) phenoxy] propionate (Diclofopmethyl; DE-OS 2 223 894 of December 13th 1973) are used as a means exclusively for combating wild oats, a very dangerous weed, applied, but their practical effect is not sufficient.

Other herbicides for wheat cultivation include, for example, 3-isopropyl-1H-2,1,3-benzothiazine- (4) -3H-one-2,2-dioxide (Bentazon; South African Patent 6,705,164, Pat. January 23, 1968 and DE-OS 1 913 85a published. October 1, 1970) and 2-chloro-N- (4-methoxy-6-methyl-1,3,5-triazin-2-yl-aminocarbonyl) -benzenesulfonamide (Chlorsulfuron; U.S. Patent 4,127,660, November 28, 197B), which have recently attracted interest as highly active compounds. The former is a connection with high security for wheat, however, its use is limited to certain broad-leaved weeds. The latter has an excellent soil treatment effect at very low doses with exceptional residual activity and is also very safe with wheat. However, it can slight phytotoxicity on the crop growing in wheat fields after the even at low dosages

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Create harvesting of wheat. Accordingly, its use is very limited. Nowadays it is with agricultural Chemicals required not only to have excellent activity, but also have a high level of safety for humans, animals and the environment.

Studies have long been made on N-phenylcarboxamide derivatives and various excellent herbicides of this type are known and become used. They are described, for example, by C.W. Hoffman et al., J. Agric. Food Chem., 8, 298 (1960) [N- (3,4-Di ~ chlorphenyl) propionamide; Propanil], in GB-PS 869 169 [Karsil, Solan] patented May 31, 1961, in the DE-PS 1 166 547 [Monalid] patented on May 26, 1964, U.S. Patent 3,816,092 issued June 11, 1974; and British Patent patented May 4, 1959. 885 043 [DCMA; Dicryl], U.S. Patent 3,277,107 [Cypromid] issued October 4, 1966, issued September 4, 1979 issued U.S. Patent 4,166,735; and U.S. Patent 3,277,171 issued October 4, 1966. Many of these compounds effectively kill weeds on foliar treatment and show a high degree of selectivity for certain types of important crops. These compounds are also expected to be proportionate decompose rapidly, and it is assumed to some extent that their action is on the growing Grain is low after harvest and that they have little residual effect on the environment. Many of these cited references say nothing about the selectivity of these compounds for wheat. The selectivities of compounds which are mentioned in some of these publications are inadequate or such connections have insufficient

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herbicidal effectiveness. Indeed, the compounds cited in these publications are the present one Wheat cultivation difficult to use.

In JP-AS 14240 / published on August 9, 1966 1966 and the DE-OS published on April 18, 1974 2,249,547 is the selectivity of N-phenylcarboxamide derivatives described for wheat, however, these compounds are not entirely satisfactory in their herbicidal properties! Effectiveness against weeds and their phytotoxicity for the grain. In particular, in the DE-OS 2,249,547 compounds of the general formula

0 R- (O) -NHC-R ¹

described, wherein R is an alkyl group having 2 to 6 carbon atoms R denotes an alkyl group having 2 to 8 carbon atoms, an alkenyl group having 3 to 6 carbon atoms or represents a cycloalkyl group having 3 to 8 carbon atoms and X represents a halogen atom. However, there are few specific compounds in the specification as examples of the above compounds actually described, and when R is isopropyl group is is just an ethyl group as an example

shown for R. Furthermore, these compounds are practically unsuitable for the reason given above.

JP-OS 193806/1984 published on November 2, 1984 and that published on February 5, 1985 JP-OS 23357/1985 describes N- (4-isopropylphenyl) carboxamide derivatives. However, these connections have disadvantages that their effects are unstable and that they are not herbicidal for some important weeds Show activity.

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It is therefore highly desirable to develop a chemical with substantial selectivity for weeds the cultivation of important grass grain species, especially wheat, and to find a chemical compound, which is little influenced by physical factors such as soil conditions (i.e. foliar treatment agents) and is a compound which shows efficacy in low dosages and a broad herbicidal Range from grass-like weeds to broad-leaved weeds and also decomposes rapidly and does not exert adverse effects such as environmental pollution.

It is an object of the present invention, a herbicide, to establish its effectiveness or phytotoxicity not of physical factors, such as soil conditions in the cultivation of wheat, which is an important cereal grass, ^first

Another object of the invention is to provide a highly selective herbicide which has an essential Selectivity for an important grass crop, especially sages, and has precise control effectiveness produced by simple foliar treatment in low doses.

Many compounds have been studied by the inventors to find a highly selective herbicide for important To develop grass cereals, especially wheat, and it has been found that, when the leaves are treated, N- (3-substituted-4-isopropylphenyl) -2-methyl-2-pentenamide derivatives have an excellent selective herbicidal effect and a very broad herbicidal spectrum, while none Phytotoxicity to major grass crops, in particular

Wheat, even when applied in very high concentrations, and that these compounds are the solve various problems described above.

It is generally assumed that compounds of the same series or structurally similar compounds have similar properties. However, it actually is not easy to derive such properties, and for example varies by simply increasing the Alkyl chain of a substituent in a herbicidal compound the herbicidal activity of the compound on weeds or its phytotoxicity on crops to a great extent.

The N- (3-substituted-4-isopropylphenyl) -2-methyl-2-pentenainide derivatives according to the invention are new compounds represented by the general formula (I)

ο / ^Y _CH

C ₀ H ₁ -CH = CCNH- (O) -CHC (D.

OT ₃ ^{W CH} 3

wherein Y represents a chlorine atom, a fluorine atom or a methyl group.

A herbicide that is an N- (3-substituted-4-isopropylphenyl) -2-methyl-2-pentenamide derivative of general formula (I) as the active ingredient controls when it is through If foliar treatment is applied, almost all dangerous highland farm weeds, e.g. very dangerous ones, are very effective Grass weeds such as wild oats (Avena fatua), meadow foxtail (Alopecurus pratensis), field foxtail (Alopecurus myosuroides), annual bluegrass (Poa annua), water foxtail (Alopecurus aequalis), millet (Echinochloa oryzicola and Digitaria

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ciliaris) and green millet (Setaria viridis); and very dangerous weeds such as wire-haired amaranth (Amaranthas retroflexus), purslane (Portulaca oleracea), pointed burdock (Xanthium strumarium), bedstraw (Galium spurium), white goose foot (Chenopodium album), chickweed (Stellaria media), Great bindweed (Ipomea purpurea), Cerastium holosteoides, Mallow (Abutilon theophrasti), Senna leaves (Cassia obtusifolia), shepherd's purse (Capsella bursapastoris), field mustard (Sinapis arvensis), Commeline (Commelina communis), Johnson grass (Sorghum helepense), Speedwell (Veronica persica), Veronica caninotesticulate, button herb (Galinsoga ciliata), common ragwort (Senecio vulgaris), common Chamomile (Matricaria chamomilla) and Urtica. On the other hand, no phytotoxicity of this herbicide is considered important Grass crops, especially wheat, observed.

The compound according to the invention shows the highest activity and the best stability of their effect when Y in formula (I) is a chlorine atom.

So have the N- (3-substituted-4-isopropylphenyl) -2-methyl ~ 2-pentenamide derivatives in accordance with the invention, substantial foliar treatment selectivity in cultivation important grass cereals, especially wheat, and can be used very safely. Various herbicides currently used in the cultivation of wheat in the Are used are soil treatment agents. The disadvantages of these herbicides, i.e. changes in effectiveness and phytotoxicity due to physical factors such as soil conditions are used in the invention Herbicide in no way observed. Furthermore, the herbicide of the present invention has little effect on the crops that are grown on the same field after the wheat has been harvested.

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The N- (3-substituted-4-isopropylphenyl) -2-methyl-2-pentenamide derivatives according to the invention can be easily synthesized by reacting a 3-substituted-4-isopropylaniline (general formula II) with a 2-methyl

2-pentenoic acid halide (general formula III) or 2-methyl-2-pentenoic anhydride according to the following Reaction s chema:

^Y \ 0 0

H ₇ C) —s- / "\

^J > C- (O V-NH _n + C ₀ Hc-CH = CCX or (CH, -CH = CC) 0 -η

CH ₃ CH ₃

(II) (III)

^H 3 ^C ^ CH ₃ (D

In the above scheme, Y represents a chlorine atom, a fluorine atom or an ethyl group and / or methyl group and X represents a halogen atom.

The reaction is carried out in the absence of a solvent or carried out in an inert solvent. Examples inert solvents include aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene and Dichlorobenzene, ketones such as acetone and methyl ethyl ketone, nitriles such as acetonitrile and propionitrile, ethers such as Ethyl ether, tetrahydrofuran and dioxane, as well as aprotic, polar solvents such as dimethylformamide, dimethyl sulfoxide and hexamethylphosphoramide. Using of the acid halide or the acid anhydride if necessary, an organic base such as triethylamine, pyridine, dimethylaniline or 1,8-diazabicyclo-

[5.4.O] -7-undecene, or an inorganic base such as potassium carbonate, sodium carbonate, sodium hydroxide, potassium hydroxide or sodium hydrogen carbonate, can be used as the acid-binding agent. The reaction temperature is -10 to 15O ⁰ C, preferably 5 to 90 ° C and especially 15 to 70 ⁰ C. The reaction can also be carried out at the reflux temperature of the solvent used. The reaction time differs depending on the reaction temperature or the solvent used. In general, it is 1 second to 10 hours, preferably 1 minute to 5 hours and in particular 20 minutes to 3 hours.

The rate of use of the N- (3-substituted-4-isopropylphenyl) -2-methyl-2-pentenamide derivative the herbicide can be selected according to the extent to which the growth of the weeds to be killed is inhibited shall be. The standard application rate is 0.1 to 10 kg / ha, preferably 0.2 to 3 kg / ha.

The herbicide according to the invention comprises the compound of the general formula (I) as a main ingredient. the Compound of formula (I) can be used directly against the plants to be treated. In general However, it is used in conventional formulations that contain a carrier and, if necessary, other auxiliaries, such as powder, granulate, wettable powder, emulsifiable concentrate or flowable agent.

Examples of carriers are inorganic materials such as clays, talc, bentonite, calcium carbonate, diatomaceous earth, Zeolite and silica anhydride; organic materials of plant origin, such as wheat flour, soybean meal,

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Starch and crystalline cellulose; polymeric compounds such as petroleum resins, polyvinyl chloride and polyalkylene glycols, Urea and waxes. Liquid carriers, oils, organic solvents and water can also be used be used.

Examples of auxiliary agents are wetting agents, dispersants, adhesives and atomizers, which if necessary can be used either alone or in combination.

Various surfactants, polymeric compounds such as gelatin, albumin, sodium alginate, methyl cellulose, Polyvinyl alcohol and xanthan gum, and other adjuvants, can be cited as auxiliaries for the purpose of wetting, dispersion, distribution, stabilization of components or stabilization used by properties. Industrial fungicides, bactericides and fungicides can be added to flowable agents for killing fungi, bacteria or fungi.

The surfactants can be nonionic, anionic, cationic or amphoteric. Examples more preferred surfactants include products of polymerization of ethylene oxide with alkylphenols, higher alcohols, alkylnaphthols, higher fatty acids, fatty acid esters or dialkylphosphoric acid amines Copolymer of ethylene oxide and propylene oxide, alkyl sulfuric acid ester salts (such as sodium lauryl sulfai}, alkyl sulfonic acid salts (Sodium 2-ethylhexene sulfonate) and aryl sulfonic acid salts (such as sodium lignosulfonate and Sodium dodecylbenzenesulfonate).

The content of the compound of the general formula (i) in the. Herbicide according to the invention varies depending on the before. of the formulation and usually it is 1 to 20 wt.% For a powder or dust, 20 to 90 wt.% For a wettable one Powder, 1 to 30% by weight for granules, 1 to 50% by weight for an emulsifiable concentrate, 10 to 90% by weight for a flowing agent and 20 to 70% by weight for a dry, flowing agent. The content of adjuvants is 0 to 80% by weight and the amount of carrier is obtained by subtracting the content of active compound and adjuvants from 100% by weight.

The herbicide according to the invention can be mixed with at least another herbicide, other agricultural chemical such as an insecticide or plant growth regulator, a soil conditioning agent and a fertilizer, applied., or can be used in one mixed agents can be formulated with such other chemicals. Sometimes this type of application can get one result in a synergistic effect.

The following examples illustrate the invention without restricting it.

Synthesis example

Production of N- (3-chloro-4-isopropylphenyl) -2-methyl-

2-pentenamide

1.0 g (5.9 10 " ³ mol) of 3-chloro-4-isopropylaniline and 0.6 g of triethylamine and a further 0.8 g (6.0 χ 10" - ⁵ mol) of 2 were added to 30 ml of benzene -Methyl-2-pentenoyl chloride and the mixture was stirred for 30 min at room temperature. The crystal precipitated was separated by filtration, and 100 ml of benzene was added to the filtrate. The mixture was washed with a saturated aqueous solution

washed by sodium hydrogen carbonate, dried over anhydrous sodium sulfate and evaporated constricted. The resulting crude crystals were made from a mixed solvent of hexane and benzene (2/1, vol / vol) recrystallized and gave 1.4 g of N- (3-chloro-4-isopropylphenyl) -2-methyl-2-pentenamide as crystals in a yield of 89.3% based on 3-chloro-4-isopropylaniline.

The compounds of the general formula (I) in which Y is a fluorine atom or a methyl group can also be used can be prepared essentially in accordance with the above procedure.

The compounds of the general formula (I) and their properties are shown in Table 1 below.

In the formulation examples and test examples given below, the active compounds designated by the compound numbers given in Table 1.

Table 1

C ₂ H ₅ CH = CCNH-CH.

CH

CH-

(D

Ver Substi- IR v ^ r cm " ¹ : 3320, 1665 properties , 1 ber. (%) .18 (6H, d, J = 8Hz), d, J f m), 2.10 (2H, m), 1 , 3.34 bind.
No. do Y NMR δjjg4: 0.95 (3H , t. (IH found (%) f m) , 7.05 (IH, J = 2Hz = 9Hz), 7. 40 1 3.64 in (I) 3.25 (IH , m), J = 9Hz, J = 2Hz) , 7. 58 (IH, d, 8.09, ), 7th (IH, dd, J = 8Hz) J = 8Hz) , 1 7.59 7.99, 7th M.p .: 71.0-73.0 ° C 6.30 (%): 3.20 (IH C; 67.78, H; 7.66, N; 5.27, Cl; m) Elemental analysis C; 67.43, H; N; 5.13, Cl; 1 Cl 1655 ber. (%) J = 8Hz), 69 IR V ^ J cm " ¹ : 3250, , t, found (%) .21 (6H, d, (IH 1.85 (3H, s), 48 NMR 6 ^ g4: 1.05 (3H f m), , m) , 6.30 7.00-7.35 (3H 2.20 (2H H; M.p .: 79.0-80.0 ° C (%): C; 72.25, H; N; 5.62, F; Elemental analysis C; 71.98, N; 5.73, F; 2 F.

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φ •O rH cc U3 Σ ^Z

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The following examples illustrate the formulation of the herbicide of the invention and its herbicidal activity.

Formulation Example 1 Wettable Powder

20 parts by weight of compound no. 1, 2 parts by weight of sodium alkylbenzenesulfonate, 2 parts by weight of polyoxyethylene alkylphenyl ether and 76 parts by weight of Zieklite (trademarks of Zieklite Chemical Industry Co., Ltd .; a carrier containing silicon dioxide as the main component) were pulverized well and mixed to form a wettable powder.

Formulation Example 2 Wettable Powder

30 parts by weight compound IJr. 3, 6 parts by weight of polyoxyethylene alkylphenyl ether ammonium sulfate, 2 parts by weight of sodium naphthalene sulfonate / formaldehyde condensate, 1 part by weight of sodium alkylbenzenesulfonate, 2 parts by weight of polyvinyl alcohol and 59 parts by weight of diatomaceous earth were pulverized well to form a wettable powder.

Formulation Example 5 Wettable Powder

50 parts / parts compound no. 2, 3 parts / parts whiter Carbon (white carbon), 4 parts by weight of polyoxyethylene alkylphenyl ether ammonium sulfate, 2 parts by weight of sodium alkylbenzenesulfonate and 41 parts by weight of diatomaceous earth were pulverized well and blended to form a wettable powder.

Formulation Example 4 Wettable Powder

55 parts by weight of compound no. 2, 5 parts by weight of white carbon,

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4 parts by weight of polyoxyethylene alkylphenyl ether ammonium sulfate, 2 parts by weight of sodium lignosulfonate and 34 parts by weight Diatomaceous earth was pulverized well and mixed together to form a wettable powder.

Formulation Example 5 Wettable Powder

80 parts by weight of compound no. 1, 5 parts by weight of white carbon, 7 parts by weight of polyoxyethylene alkylphenyl ether ammonium sulfate, 2 parts by weight of sodium naphthalenesulfonate / formaldehyde condensate, 2 parts by weight of sodium alkylbenzenesulfonate and 4 parts by weight of diatomaceous earth were used pulverized well and blended to form a wettable powder.

Formulation Example 6 Flowable Agent

76.7 parts by weight of water were mixed with 20 parts by weight of the compound No. 1, 2 parts by weight of sodium lignosulfonate, 0.3 part by weight of xanthan gum and 1 part by weight of polyoxyethylene alkylaryl ether mixed. The mixture was finely pulverized by a sand mill to give a flowable one Funds to form.

Formulation Example 7 Flowable Agent

52.8 parts by weight of water became 40 parts by weight of the compound No. 2, 3 parts by weight sodium naphthalene sulfonate / Formaldehyde condensate, 2 parts by weight sodium lignosulfonate, 0.1 part by weight xanthan gum, 0.1 part by weight Deltop (registered trademark of Takeda Chemical Co., Ltd .; industrial fungicide containing an organic iodoacetamide compound as the main active ingredient

part) and 2 parts by weight of polyoxyethylene alkylaryl ether. The mixture was taken using a sand mill Forming a flowable agent finely powdered.

Formulation Example 8 Dusts

3 parts by weight of compound no. 1, 3 parts by weight of sodium lignosulfonate, 2 parts by weight of polyoxyethylene alkyl aryl ether and 92 parts by weight of clay were mixed and pulverized to obtain to form a dust.

Formulation Example 9 Dusts

20 parts by weight of compound no. 3, 5 parts by weight of sodium lignosulfonate, 4 parts by weight of polyoxyethylene alkyl aryl ether and 71 parts by weight of clay were mixed and pulverized to make to yield a dust.

Formulation Example 10 Dry, flowable medium

60 parts by weight of compound no. 1, 5 parts by weight of sodium alkylbenzenesulfonate and 35 parts by weight of polypropylene glycol polyethylene glycol ether were finely powdered using a Jet-O mixer to a dry, flowable Funds to surrender.

Formulation Example 11 Dry, flowable agent

70 parts by weight of compound no. 2, 2 parts by weight of sodium alkylbenzenesulfonate, 18 parts by weight of polypropylene glycol polyethylene glycol ether and 10 parts by weight of white carbon were finely pulverized using a Jet-O mixer, to give a dry, flowable agent.

Formulation Example 12 Granules

20.5 parts by weight of finely powdered compound Mr. 3, 2.0 parts by weight of Gohsenol GL-5S (Viarenzeichen of Nihor. Synthetic Chemical Co., Ltd .; polyvinyl alcohol), 2.0 parts by weight of Sunexs P-252 ( Trademarks of Sanyo Kokusaku Pulp Co., Ltd .; sodium lignosulfonate) and 75.5 parts by weight of clay were mixed well, and an appropriate amount of water was added to moisten the mixture. The skeleton was then extruded through an injection molding machine to produce granules. The granules were air-dried at 60 to 70 ⁰ C, crushed and a Eorndurchmesser of 0.3 to 1 mm by means of a set size vision machine.

Formulation Example 13 Granules

5 parts by weight of finely powdered Compound No. 1, 72 parts by weight of bentonite, 20 parts by weight of talc, 2 parts by weight of calcium dodecylbenzenesulfonate and 1 part by weight of calcium lignosulfonate were mixed well, and an appropriate amount of water was added to moisten the mixture. The mixture was extruded through an injection molding machine to produce granules. The granulate was air-dried at up to 90 ^° C., comminuted and adjusted to a diameter of 0.5 to 1.2 mm.

Formulation Example 14 Granules

12 parts by weight of finely powdered compound No. 2, 60 parts by weight of bentonite, 25 parts by weight of talc, 2 parts by weight Sodium naphthalene sulfonate / formaldehyde condensate and 1 part by weight of dioctyl sulfosuccinate was mixed well

and a suitable amount of water is added to moisten the mixture. The mixture was extruded through an injection machine to form granules. The granules were air-dried at 60 to 9O ⁰ C, crushed and adjusted to a diameter of 0.3 mm to first

Formulation Example 15 Emulsifiable Concentrate

10 parts by weight of compound no. 2, 10 parts by weight of Sorpol 800A (Trademark of Toho Chemical Co., Ltd .; a mixture of nonionic and anionic surfactants Agents) and 80 parts by weight of benzene were mixed and dissolved to give an emulsifiable concentrate.

Formulation Example 16 Emulsifiable Concentrate

50 parts by weight of Compound No. 3, 15 parts by weight of Gafac RS-610 (Trademark of General Aniline & Film Corp .; polyoxyethylene phosphate) and 35 parts by weight of o-xylene mixed and dissolved to make an emulsifiable concentrate.

Formulation Example 17 Emulsifiable Concentrate

25 parts by weight of compound no. 1, 15 parts by weight of Plysurf A-210G (trademark of Dai-ichi Kogyo Seiyaku Co., Ltd .; Polyoxyethylene phosphate) and 60 parts by weight of o-xylene were mixed and dissolved to obtain an emulsifiable To give concentrate.

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Test example 1

Plastic pots (1/10 000 ares) were filled with soil from a Kochland farra and seeds of one variety of the test plant are sown in each pot and grown in a greenhouse. When each plant is on a At stage 2 or 3 leaves have grown, each of the test compounds in acetone is polyoxyethylene sorbitan monooleate and contains sorbitan monolaurate, dissolved. The solution was made using a pressure micro-atomizer sprayed at a rate of 2 kl / ha. The chemical became effective on the 21st day after spraying observed and examined for the crop and the weeds. The results are shown in Table 2. The degree of damage to the test plants was evaluated according to the following scale. Assessment Degree of Damage State of Damage

5 100 withered (complete Be

rule of weeds)

4 80 very severe damage

(80% weed control)

3 60 moderate damage (6055

Weed control)

2 40 minor damage (40> p

Weed control)

1 20 slight damage (20%

Weed control

0 0 no damage (none

Weed control j

The control compounds in Table 2 were as follows:

A: N- (3,4-dichlorophenyl) propionamide (propanil);

3: N- (3,4-dichlorophenyl) -2-methylpentanamide (Karsli) (GE-PS 869 169);

C: N- (3-chloro-4-methylphenyl) -2-methylpentanamide (Solan) (GB-PS 869 169)

D: M- (3,4-dichlorophenyl) methacrylamide (Dicryl) (GB-P3 385 043).

2k

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Test example 2

A plastic planter (1/1000 a) was filled with the soil from a highland farm and seeds of Avena fatua L., Alopecurus aequalis, Poa annua L., Stellaria media, Chenopodium album and Polygonum convolvulus as weeds were sown in the container. At the same time, egg seeds (variety Nor in No. 61) and barley (variety Tochigi Sekitori No. 1) were sown as useful plants in the vessel. These plants were cultivated in a Phytotron (12 to 18 ⁰ C). When the wheat had grown to the stage of 2 or 3 leaves, a predetermined amount of each of the test compounds formulated as in Formulation Example 15 was diluted with water in an amount corresponding to 500 / ha and applied by a microsprayer. In the third week after the treatment with the chemical, the effect of the chemical on the weeds and the crops was observed and evaluated. The results are given in Table 3. The degree of damage to the test plants was evaluated according to test example 1.

The control compounds given in Table 3 are the following:

E: N- (4-isopropylphenyl) -2-methyl-2-pentenamide (Japanese Patent Laid-Open No. 23357/1985);

F: N- (3-chloro-4-isopropylphenyl) propionamide (DE-PS 2,249,547);

G: N- (3-chloro-4-methylphenyl) ^ -methyl ^ -pentenamide (GB-PS 885 043).

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Test example j Test on a wheat field

A wheat cultivation field trial was conducted in Chigasaki City, Kanagawa, Japan in October 1984. Wheat seeds (variety Norin No. 61) and barley (variety Tochigi Sekitori No. 1) were sown on October 19th. All weeds were allowed to occur spontaneously. On November 13th, each of the test chemicals was given in an appropriate amount 500 l / ha sprayed by means of a battery-powered sprayer. At that point the wheat was gone at the 3-leaf stage and the barley at the 2.5-leaf stage. The test areas had one dimension of 2 m by 2.5 m and the test was carried out by 2 replicates. On December 4th, the 41st day after spraying the chemical, the effect of the agent was evaluated. The degree of damage to the test plants was rated on a scale of 11 divisions, with "10" meaning complete kill and "0" none Effect means. The results are shown in Table 4. Each rating was an average of the ratings in the two replicas. The compounds according to the invention were used in the form of an emulsifiable concentrate prepared according to formulation example 17. the Control compounds used were commercially available Stam (emulsifiable concentrate), Tribunil (wettable Powder) and Basagran (liquid preparation).

Stan: trademark of Rohm & Haas Company; a herbicide containing N ~ (3,4-dichlorophenyl) propionamide (Propanil) as the main effective ingredient?

Tribunil: trademark of Bayer AG; a herbicide containing 3- (2-benzothiazol-2-yl) -1,3-dimethylurea (Methabenzthiazuron) as the main effective ingredient;

Basagran: trademark of BASF AG; a herbicide containing 3-isopropyl-1H-2,1,3-benzothiadiazin-4 (3H) -one-2,2-dioxide as an effective main ingredient.

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3601H8

The abbreviations used to denote the in the Plants tested in Tables 2, 3 and 4 have the following meanings.

Scientific name e

(a) Digitaria ciliaris

(b) Steria viridis

(c) Echinochloa oryzicola

(d) Avena fatua L.

(e) Poa annua L.

(f) Amaranthas viridis L.

(g) Chenopodium album (h) Stellaria media (i) Sinapis arvensis

(j) Polygonum colvolvulus (k) Xanthium strumarium (l) Ipomea purpurea

(m) Alopecurus aequalis

(n) Matricaria chamomilla

(o) Capsella bursa-pastoris

(p) Lamium amplexicaule

(q) Veronica persica

(r) Oryza sativa

(s) Triticum

(t) Zea mays

(u) Arachis hypogaea

(v) Glycine max

(w) Hordeum vulgar

The above test results show that the herbicides containing the compounds of the invention a pronounced herbicidal effectiveness in low doses against all tested weeds by foliar treatment show without affecting the soil, while showing exceptional selectivity for useful grass crops, especially wheat, and that they could use the previous pesticides or others known compounds such as Methabenzthiazuron, Bentazon, Propanil, Karsil, etc., surpass.

Claims (6)

Claims 1. H- (3-substituted-4-isopropylphenyl) -2-methyl-2-pentene- W amide derivative of the following general formula> C _o H "-CH = CCNH- (O) ^CH ^ CH ₃ 3 wherein Y represents a chlorine atom, a fluorine atom or a methyl group. 2. A compound according to claim 1, wherein Y is a chlorine atom. 3. Compound according to claim 1, wherein Y is fluorine atom means. 3601U8 4. A compound according to claim 1, wherein Y is a methyl group means. 5. Process for the preparation of an N- (3-substituted-4-isopropylphenyl) ^ - methyl ^ -pentenamide derivative of the general formula (I) O Z _CH ³ (D CH ₃ ^{W CH} 3 wherein Y is a chlorine atom, a fluorine atom or a methyl group means, characterized in that an aniline of the general formula (II) ^ CH ₃ { wherein Y is as defined above, with a 2-Me- * ethyl-2-pentenoic acid derivative of the general formula (III) CH ₃ CH ₂ CH = CCX (III) CH ₃ wherein X is halogen, or with 2-methyl-2-pentenoic anhydride is implemented. 6. Selective herbicide, comprising an N- (3-substituted-4-isopropylphenyl) -2-methyl-2-pentenamide derivative of the general formula _λ γ / -CH. C ₀ H ₁ -CH = CCNH- ' CH ₃ wherein Y represents a chlorine atom, a fluorine atom or a methyl group as an active ingredient.