DE2226593B2 - HALOGEN ACETANILIDE DERIVATIVES AND HERBICIDE PREPARATIONS CONTAINING THESE - Google Patents

Description

wherein

A>NH,> N- (C = O) _n , -R ⁴ , oxygen or sulfur,

Y means oxygen or is sulfur, when A is sulfur,

R lower alkyl and

R ^{1 are} hydrogen or lower alkyl and can be identical or different,

R ^{2 is} hydrogen or methyl,

R ^J hydrogen, lower alkyl, lower dialkylamino, lower alkenyl, lower alkoxyalkyl, lower haloalkyl, cyclopropyl, aryl, 2-hydroxyphenyl, aryloxyalkyl, haloaryl, haloaryloxyalkyl, arylalkyl, arylalkenyl, nitroaryl, halonitrophenyl, 3-pyridyl, -Pyridyl, 3,4-Meihylenedioxyphenyl, Amino, Haloamino-phenyl,

R ^{4 is} lower alkyl or R ¹ and R ⁴ are connected to one another to form an alkylene bridge with 2 or 3 carbon atoms,

X is chlorine, bromine or iodine and

η has the value 1 or 2 and m has the value O, or has the value 1 if R ¹ and R ⁴ are linked to form an alkylene bridge with 2 carbon atoms.

2. Herbicidal preparation, characterized by the content of a compound of claim 1 and a common tool.

The present invention relates to haloacetanilide derivatives which have herbicidal properties as well herbicidal preparations which contain these compounds.

The haloacetanilide derivatives according to the invention have the general formula

Il

RC CH ₂ X

■ / ' N Y

,, Λ4- - ■ ü

R ¹ (CH ₂ I ,, Λ C -R- ¹

wherein

A>NH,> N - (C = O) ,,, - R ⁴ , oxygen or sulfur.

Y means oxygen or is sulfur, when A is sulfur,

R lower alkyl and

R ^{1 are} hydrogen or lower alkyl and can be the same or different,

R ^{2 is} hydrogen or methyl,

R ^{3 is} hydrogen, lower alkyl, lower dialkylamino, lower alkenyl, lower alkoxyalkyl, lower haloalkyl, cyclopropyl, aryl, 2-hydroxyphenyl, aryloxyalkyl, haloaryl, haloaryloxyalkyl, arylalkyl, arylalkenyl, nitroaryl, halo-nitrophenyl, 2-pyridyl, 3-pyridyl -Pyridyl, 3,4-methylenedioxyphenyl, amino, halo-aminophenyl,

R ^{4 is} lower alkyl or R ³ and R ⁴ are connected to one another to form an alkylene bridge with 2 or 3 carbon atoms,
ι s X is chlorine, bromine or iodine and

η has the value of 1 or 2 and m has the value O, or has the value 1, if R ³ and R ⁴ are linked to form an alkylene bridge with 2 carbon atoms.

The herbicidal preparations of the present invention are characterized by the content of a compound of the above general formula and a customary auxiliary.

The alkyl and alkoxy groups can be primary, secondary or tertiary groups.

Typical compounds of the present invention are those in which the individual Substituerites of the general ones given above

yo formula, for example, have the following meanings:

R methyl, ethyl, propyl, isopropyl, η-butyl, primary isobutyl, secondary isobutyl, tertiary butyl,

.15 n-amyl, branched-chain amyls, the nc rmalen and branched hexyls, heptyls, octyls, nonyls, and decyls.

R ^{1 is} hydrogen, methyl, ethyl, propyl, isopropyl, n-butyl, primary isobutyl, secondary isobutyl, tertiary butyl, n-amyl, branched chain amyls, the normal and branched hexyls, heptyls, octyls, nonyies and decyls.

R ^J hydrogen, methyl, ethyl, propyl, isopropyl, n-bulyl, primary isobutyl, secondary isobutyl, tertiary butyl, the normal and branched amyls, hexyls, heptyls, octyls, nonyls, decyls, chloromethyl, bromopropyl, iodobutyl, fluorohexyl, the Alkenyl and alkoxyalkyl groups corresponding to the above-mentioned alkyl groups, phenyl, ToIyI, naphthyl, benzyl or phenoxyalkyl.

R ⁴ The alkyl groups of R ^J.

Preferred haloacetanilide derivatives of the present invention are those in which both radicals R and R ^{1 are} ethyl, and in particular the compounds in which they are in the ortho positions.

The haloacetanilide derivatives of the present invention, wherein A is the> NH group and η is 1. are by means of a Carboniuinionen-Re-

fio action of a 2-halogen-N- (substituted methyl) -acetatiilids with a nitrile or an inorganic cyanide produced under acidic conditions. The haloacetanilide derivatives of the present invention, wherein η is I and A is oxygen or sulfur,

(, s are made in a similar way to what a Reacts 2-halo-N- (substituted methyl) acetanilide with a monocarboxylic acid. The methyl substituent can be any group leading to the formation of a

: is suitable for arboniumions and can easily be displaced or replaced under acidic conditions. The starting material can therefore be a 2-halo-N-ethylacetanilide in which the methyl group is substituted by a halogen atom, an alkoxy, alkylthio, hydroicy, mercapto, alkenoyloxy and similar leaving group. However, it is particularly preferred to use a 2-halo-N-chloromethylacetanilide for the preparation. A solvent can be used, but in most cases it is not required. Although the reaction can be carried out at temperatures of about 0 ^° C., in order to accelerate the reaction it is generally preferred to carry it out under reflux at the boiling point of the nitrile or of the solvent present in the system. After the reaction is substantially complete, the reaction mixture is quenched with water and filtered to recover the acetanilide which can then be purified in conventional manner.

The 2-halo-N- (substituted methyl) acetanilide used as the starting material in these reactions is the adduct of a haloacetic acid derivative, such as the halide or anhydride, with one substituted azomethine or methylene arylamine. The azomethines are made suitable by reacting one substituted aniline made with formaldehyde. The 2-halo-N-halomethylacetanilide used to manufacture of the present compounds can be used are in U.S. Patent 3,637,847 described.

The haloacetanilide derivatives of the present invention, in which A denotes the> NH group and η has the value 1, can also be prepared by treating a nitrile with an <x-halo-disubstituted-N- (alkoxymethyl) -acetanilide in the manner described in US Pat. No. 3,442,945.

The haloacetanilide derivatives of the present invention, wherein A is the group N- (C = O) ,,, - R ⁴ and m and η are both 1, are prepared by reacting a substituted methylene arylamine with an appropriately substituted amide or Imide produces the corresponding N (anilinomethyl) amide or imide. The amide or imide intermediate is then haloacetylated with a haloyl halide to form the compounds of interest.

The haloacetanilide derivatives of the present invention, wherein A. is the> NH group and η is 2, are easily prepared by chloroacetylation of N- (substituted phenyl) -N'-acyl-ethylene diamine. The haloacetanilide derivatives of the present invention, wherein A is the group N- (C = O) ₁₁₁ -R ⁴ and m is 0 or I, are prepared in a similar manner by haloacetylation of an N- (substituted phenyl) -N'- acyl-N '- (C = O), "- R ⁴ -ethylenediamine. The ethylenediamine derivatives which are used as starting materials for such reactions can easily be prepared in a conventional manner by adding a substituted aniline with alkylating agents such as an N- (2-chloroethyl) -alkylamide, N-2- (hydroxyethyl) - alkylamici, N- (2-bromoethyl) phthalamide or N-acylaziridine alkylated.

The novel compounds of the present invention. (^ where A is oxygen or sulfur and π is 2 are readily made by pinene N-substituted phenyl) ethyl esters of the general

a formula

-NH-CH ₁ -CH ₅ -OCR ³

.χ R

in which the radicals R, R ¹ , R ² and R ^{3 have} the meaning given above, chloroacetylated.

The ethyl ester derivatives used as starting materials for such reactions can easily be in conventionally by alkylating a substituted aniline with alkylating agents such as N- (2-chloroethyl) ethyl ester or N-2- (hydroxyethyl) ethyl ester.

The invention is further illustrated by the following detailed description of specific examples. In these examples and in the description, all parts are given in parts by weight unless something else is expressly said.

example 1

This example describes the preparation of 2-chloro-N- (2 ', 6'-d; ethylphenyl) acetamidomethyl chloroacetate. About 168 parts of 2 ', 6'-diethylphenylazomethine dissolved in benzene were slowly added to about 177 parts of chloroacetic anhydride dissolved in hot benzene. The reaction mixture was stirred until the reaction was complete, then concentrated and quenched. A white solid was obtained; Melting point 57 to 58 ° C.
Analysis for C ₅ H 19NCL ₂ O ₃ :

Calculated: C 54.27, H 5.88%;

found: C 54.19, H 5.91%.

Example 2

This example describes the preparation of 2-chloro-2 ', 6'-diethyl-N- (acetamidomethyl) acetanilide. About 80 parts of 2-chloro-N (2 ', 6'-diethylphenyl) acetamidomethyl chloroacetate, prepared by the general procedure of Example 1, were mixed with about 1000 parts of methyl cyanide and about 2 parts of 10% sulfuric acid in a suitable reaction vessel mixed. The reaction mixture was refluxed for approximately 2.5 hours at atmospheric pressure and then poured into an ice / water mixture. The solid material obtained in this way was recrystallized from methanol and had a melting point of 148 to 149 ° C. Analysis for C, ₅ H ₂ | CIN ₂ O.>:

Calculated: C 60.7, H 7.13%;

found: C 60.68, H 7.22%.

Example 3

This example describes the preparation of 2-chloro-2 ', 6'-diethyl-N- (2 ", 6" -dichlorobenzamidomethyl) -acetanilide. Approximately 100 parts of 2-chloro-N-chlormeihyi-2 ', 6'-diäihyl-acetanilide were added to about 350 files sulfuric acid in a suitable reaction vessel, cooled to 0 ⁰ C and stirred. About 7 parts of 2,6-dichlorophenyl nitrile were slowly added to this mixture. After complete addition of the nitrile, the Reaktionsgcmiscli was heated for approximately 1.5 h with constant stirring aiii about 75 ¹ C. The reaction mixture was then poured into ice water and a light brown egg dye precipitated. This was through Filtratior

separated off, washed with water, filtered and recrystallized from toluene. A material was obtained with a melting point of 150.5 to 153 ° C.

Calculated: C 55.16, H 4.95%; Found: C 55.69, H 4.85%.

Example 4

This example describes the preparation of 2-chloro-2 ', 6'-diethyl-N- (3-butenamidomethyl) -acetani- ι ο lid. Approximately 300 parts of sulfuric acid was placed in a suitable reaction vessel. About 100 parts of 2-chloro-N-chloromethyl-2 ', 6'-diethyl acetanilide and about 26 parts of allyl nitrile, dissolved separately in glacial acetic acid, were added to the sulfuric acid. The reaction mixture was then heated to about 55 ° C for about 15 minutes and then poured into ice water. The solid precipitate obtained was filtered off and washed with water. After recrystallization from isopropanol the product has a melting point of 121.5 to 123.5 ⁰ C. had
Analysis for Ci ₇ H ₂₃ CIN ₂ O ₂ :

Calculated: C 63.25, H 7.18%;

found: C 62.38, H 6.95%.

Example5

This example describes the preparation of 2-chloro-2 ', 6'-diethyl-N- (formamidomethyl) -acetariilide. About 200 parts of 2-chloro-N-chloromethyl-2 ', 6'-diethyl-acetanilide was added to 400 parts of concentrated sulfuric acid yo. The mixture was ^{cooled to approximately 10 °} C., 70 parts of sodium cyanide were added and the mixture was heated ^{to approximately 50 ° C.} Due to the exothermic reaction, the temperature of the reaction mixture rose to about 85 ⁰ C. The reaction mixture was then cooled, poured into ice water, extracted with methylene dichloride, washed with water and dried over magnesium sulfate. The oily residue was recrystallized first from ether and then from a mixture of methylcyclohexane-HOluol; Melting point 85 to 89 ° C.
Analysis for Ci ₄ HI ₉ ClN ₂ O ₂ :

Calculated: C 59.46, H 6.77%;

found: C 59.64, H 6.69%.

Examples

This example describes the preparation of 2-chloro-2 ', 6'-diethyl-N- (3-chloro-2-methylpropionamidomethyl) acetanilide. About 100 parts of 2-chloro-N-chloromethyl-2 ', 6'-diethyl-acetanilide were mixed with 26 TEI v> len methacrylonitrile mixed and added to a suitable reaction vessel to about .350 parts of sulfuric acid at a temperature of about 10 ⁰ C . The reaction mixture was heated to about 65 ° C for about 4 hours while dry hydrogen chloride was bubbled through. The reaction mixture was then poured into ice water and filtered to remove the precipitate, which was then recrystallized from isopropanol.
Analysis TUrCi ₇ H ₂₄ Cl-N ₂ O .: «>.

Calculated: C 56.8-} .. HfilWii:

found: C 56.85, H 6.62%.

Example 7

This example describes the preparation of <·> 2-chloro-2 ', 6'-diethyi-N- (ucrylamidomethyl) -acetanilide. About 135 parts of 2-chloro-2 ', 6'-diethyl-N-methoxymethyl acetanilide were mixed with about 27 parts of acrylonitrile and about 300 parts of sulfuric acid were added. The reaction mixture was then ^{heated to approximately 55 °} C. and held at this temperature for approximately 1 hour. It was then poured into ice water to give a solid granular precipitate which was separated by filtration, washed with water and recrystallized from isopropanol. The recrystallized material had a melting point of 174-175 ° C. Analysis for C, ₆ H ₂ | CIN ₂ O ₂ :

Calculated: C 62.23, H 6.85%;

found: C 62.54, H 7.05%.

Example 8

This example describes the preparation of 2-chloro-2'-ethyl-6'-methyl-N- (cyclopropanecarboxamidomethyl) acetanilide. Approximately 300 parts of concentrated sulfuric acid were placed in a suitable reaction vessel and cooled ^{to approximately 0 ° C. with stirring.} About 100 parts of 2-chloro-2'-ethyl-e'-methyl-N-chloromethyl-acetanilide were then slowly added and the mixture was heated to about 25 ° C. in order to accelerate the dissolution of the adduct. The mixture was cooled again to about 10 ^° C. and then about 28 parts of cyclopropyl nitrile were slowly added. After the addition of the nitrile was complete, the reaction mixture was ^{heated to about 55 °} C. for about 20 minutes and then poured into ice water. A resinous precipitate formed which solidified after standing for about 8 hours. The solid precipitate was separated off by filtration, washed with water, filtered and recrystallized from isopropanol; Melting point 154 to 156.5 ⁰ C.

Example 9

Preliminary stage for example 10

N- (2,6-diethylanilinomethyl) -N-methylacetamide

O Il CH,

NH-CH ₁ -N

C-CH ₃

CH ₃

In a suitable reaction vessel, approximately 100 parts of N-methylacetamide were placed and approximately 100 parts of 2% sodium methoxide suspension in dimethylformamide were added.

The exothermic reaction increased the temperature of the reaction mixture from about 24 to about 30 ° C. Then approximately 160 parts of 2,6-diethyl N-methyleneaniline were added, whereby another i The temperature increased to approximately 44 ° C. The reaction mixture was continued with continued Stir at this temperature for about 7 hours; held. After the stirring was stopped, the ( Mix down to room temperature after about 16 hours. It then became about 3 parts acetic acid and then about 200 parts of water zucgcbci and da >> The mixture was stirred vigorously, and approximately 150 parts of benzene were used to aid the separation Mixture added in an oil and a water layer. The water seal was discarded and the Oil layer washed with a further 200 parts of water containing 1 part of acetic acid, over magnesium sulfate

dried and distilled in vacuo. Mim received a straw-colored liquid which was identified as N- (2, b-diethylanilinomethyl) -N-methylacetamide.
Analyst for Ci jH ^ NiO:

Calculated: C 71.75, H 9.46. N 11.95%;

found: C 71.90, H 9.54, N 12.05%.

Example 10

2-chloro-N- (N-methylacetamidomethyl) -2 ', 6'-diethylacetanilide

IS

CH

CH ₂ -N C-CH.,

About 72 parts of N- (2,6-diethylanilinomethyl) -N-methylacetamide obtained by following the procedure of Example 9 were dissolved in about 100 g of toluene, placed in a suitable reaction vessel, and about 40 parts of 2,6-lutidine admitted. The mixture was quenched with carbon dioxide / acetone and about 40 parts of chloroacetyl chloride were added under vigorous stirring in 70 parts of benzene over 15 minutes keeping the temperature of the reaction mixture from -20 to -30 ⁰ C. The reaction mixture was allowed to warm to room temperature with continued stirring. About 100 parts of water were then added and the mixture was separated into an oily fraction and an aqueous fraction. The aqueous fraction was discarded and the oily fraction was washed twice with 150 parts of water at a temperature of about 35 ° C. The reaction mixture was then evaporated to practically dryness in vacuo and first 100 parts of methylcyclohexane and then about 15 parts of benzene were added to the residue to form a homogeneous solution. The product crystallized out of the solution after standing and was separated from the liquid phase by filtration, washed with a mixture of methylcyclohexane / benzene for 4 seconds and then dried in the air. After recrystallization from a benzene / hexane mixture a cream colored product was obtained having a melting point 82 to 83 ⁰ C. SO

Calculated: C61.83, H 7.46, Cl 11.41. N 9.01%;

found: Cbi.bS. 117.47, Cl 11.48. N 8.97%.

Example 11

2-chloro-2 ', b'-diethyl-N- (succinimidomethyl) - ss

acetanilide

C ₂ H ₅

("η I

C (ΊΙ, Π

CH, N-

O C-

Il

CH ₁
CH,

do a mixture of about 30 parts of 2, b-diethyl N-methyl-methyl-niline, 20 parts of suecinimide and / 5 parts

Dimethylformamide was heated in a suitable reaction vessel at a temperature of approximately 90 to 95 ° C. for 18 hours. The reaction mixture was then evaporated in vacuo to give a residue which contained N- (2,6-diethylanihnomethyl) suecinimide. The residue was dissolved in approximately 150 parts of toluene and approximately 30 parts of 2,6-lutidine were added. The mixture was cooled to about -10 ° C and about 2J parts chloroacetyl chloride was added in portions over the course of 20 minutes, the temperature of the reaction mixture being kept between about -10 ° and f> ° C. A heavy precipitate formed. The reaction mixture became then cooled to about 0 ^° C., kept at this temperature for 1 hour and then the precipitate was removed from the dark mother liquor. The precipitate was washed with dilute hydrochloric acid, water and toluene, then recrystallized from a methylcyclohexane / ethyl acetate mixture, whereby a gray powder with a melting point of 146 to 147 ° C. Analysis for Ci ₇ HJiCIN ₂ Oj:

Calculated: C 60.62, H 6.28, Cl 10.53, N 8.32%; Found: C 60.90, H 6.25, Cl 10.53, N 8.25%.

Example 12

2-chloro-2 ', 6'-diethyl-N - [(2-pyrrolidinon-1-yl). Methyl] acetanilide

C ₂ H ₁₁

C \ U NC C \ U

ILC

■ πι,

About 40 parts of N- (2,6-dialhylanilinomethyl) -2-pyrrolidinone were dissolved in about 100 parts of toluene, and about 30 parts of 2,6-l-butidine were added to the solution. The mixture was then cooled ^{to approximately -30 3 C with constant stirring.} Approximately 23 parts of chloroacetyl chloride, dissolved in approximately 80 parts of toluene, were added over the course of 15 minutes, the temperature being kept between -20 and -3O ⁰ C. When the addition was complete, the temperature was allowed to rise to room temperature and approximately 100 parts of water were added. An oil fraction formed and an aqueous fraction formed. The latter was discarded and the remaining C was washed with water and stripped off under vacuum. The oily residue was dissolved in a mixture of 10 parts of methylcyclohexane and 20 parts of benzene. The product which precipitated from this mixture on standing was after Recrystallization from a mixture of methylcyclohexane / benzene obtained in the form of colorless granules; Melting point 5b to 57 "C.
Analysis for CwIImCIN / O ^

Calculated: C 63.25, H 7.18, Cl 10.98%; found: Cb3.3b, Il 7.33. Cl 11.02%.

7Ü9b3b / 1

Example 13

Example 15

Precursor for compounds according to the invention

N- (2,6-Dialhylaniunomethyl) -N, N'-trimethyloxamicl

C ₂ H ₅

CH, -N - C -CN (CH ₃ ),

CH,

About 650 parts of Ν, Ν ', Ν'-trimethyloxamide and ι about 4 parts of potassium hydroxide pellets were placed in a suitable reaction vessel, about 800 parts of 2,6-diethylphenylazomethine and then about 5 parts of a 25% solution of sodium methoxide in methanol were added. The reaction _proceeded: slowly, maintaining the temperature in 15 minutes from room temperature to about 50 "C rise, and then dropped to about 45 ° C The mixture was then heated with constant stirring to about 100 ⁰ C and then to room temperature (about 23rd The honey-like syrup obtained, which contained small amounts of unpolluted potassium hydroxide pellets, was dissolved in 2500 parts of methylcyclohexane and acidified with about 10 parts of acetic acid. After stirring the reaction mixture, the product crystallized to form colorless granules, which were filtered and twice with 1200 Parts of methylcyclohexane were washed. Zulct / Λ the product was washed three times with 1500 parts of water and air-dried; melting point 73 to 73.3 "C. Analysis for C ¹ IhHy ₁ NiO .:

Calculated: C 65.9, 118.6, N 14.4%; found: C 65.9, H 8.6, N 14.4%.

These and related compounds having two adjacent carbonyl groups can be readily haloacetylated to give compounds of the present invention in which η is I.

Example 14

This example describes the preparation of 2-chloro-2 ', 6'-diethyl-N- (propionyloxymethyl) -ucetanilide. About 140 parts of 2-chloro.2'.6'-diethyl-N-chloromethylucetanilide, dissolved in tetrahydrofuran, were placed in a suitable reaction vessel and a A solution of approximately 40 parts of propionic acid in tetrahydrofuran was added. After the (ionic in was substantially homogeneous, approximately 55 parts of triethylamine were added portionwise. The solution was then heated to reflux, refluxed for approximately 3 hours and then up Cooled to room temperature. The resulting precipitate was separated off by filtration in diethyl ether added, the ethereal solution with aqueous sodium bicarbonate solution, then washed with water and dried over magnesium sulfate. The solution was then vacuum stripped and the oily residue obtained recrystallized from hexane after solidification. A white solid was obtained with a melting point of 64 to 65 C. Analysis for CifcHjiCINOi:

Calculated: C 61.63, H 7.11%;

found: C 61.94, 117.04%.

This example describes the preparation of 2-chloro-2 ', 6'-diethyl-N- (formyloxymethyl) acetanilide. About 140 parts of 2-chloro-2 ', 6'-diethyl-N-chloromethylacetanilide, dissolved in tetrahydrofuran, was placed in a suitable reaction vessel and approximately 25 Parts of 99% formic acid and 50 parts of triethylamine were added. The reaction mixture then became approximately Heated to reflux for 3 hours and cooled to room temperature. The tetrahydrofuran was Stripped from the mixture by vacuum distillation, the residue dissolved in diethyl ether and the ethereal solution washed first with aqueous sodium bicarbonate, then with water and lastly over Dried magnesium sulfate. Obtained by distilling the essential solution in vacuo at 65 "C75Torr a clear oily residue paint. Analysis for CuHigCINOi:

Calculated: C 59.26, H 6.39%;

found: C 59.32, H 6.47%.

> s B e i s ρ i e I 16

This example describes the preparation of 2-chloro-2 ', 6'-diethyl-N- (butyryloxymethyl) acetanilide. About 200 parts of 2-chloro-2 ', 6'-diethyl-N-chlorine-

thylacetanilide dissolved in tetrahydrofuran was placed in a suitable reaction vessel, stirred well and with continued stirring, about 70 parts of n-butcheric acid and about 80 parts of triethylamine in portions admitted. The reaction mixture became approximately 3 months

is refluxed for hours, at room temperature cooled, filtered and the Filtral stripped by vacuum distillation. The residue was dissolved in diethyl ether dissolved, washed with aqueous sodium bicarbonate, then with water and over magnesium sulfate

i <> dried. The magnesium sulfate was removed by filtration and the solvent stripped by distillation at 6O ⁰ CVI Torr. The residue obtained in this way was a tan-orange-colored oil. Analysis for Ciill.ΛΊΝΟ ,:

. |> Calculated: C 62.66, 117.42%;
found: C 63.01, H 7.71%.

Example 17

This example describes the preparation of 2-chloro-2 ', 6'-diethyl-N- (ucrylyloxymethyl) -aeetanilide. About 200 parts of 2-chloro-2 ', 6'-diethyl-N-chloromethylacctanilide, 55 parts of acrylic acid, and about 80 parts of triethylamine were reacted in essentially the same manner as in the previous example to give an almost white solid with a melting point from 91 to 96 "C. Analysis for Cu ₁ I-IiOCINO ₁ :

Calculated: C 62.03, 116.51%; found: C 62.66, 116.59%.

Example 18

Analogously to the procedure of the preceding examples, using cyclopropanecarbonsitin as the reaction pariner, 2-chloro-2 '" ₎ 6'-diethyl-N- (cyclopro

11th

pancarbonyloxymelhyl ^ aeetanilide with a melting point obtained from 84 to 87 ° C.

Calculated: C 63.05, H 6.85%; found: C 63.43, 117.00%.

Examples 19 to

The following compounds were prepared analogously to the methods of the preceding examples:

(28) (29) (JO) (31) (32)

2-chloro-2 ', 6'-diethyl-N- (cinnamic acid amidomethyl) -acetanilide, Melting point 146 to 147 "C.

2-chloro-2 ', 6'-diisopropyl-N- (butyramidomethyl) acetanilide.

2-bromo-2 ', 3', 6'-triniethyl-N- (acetamidomethyl) acetanilide.

Melting point 131 to I 32 "C.

2- | od-2 ', 6'-diethyl-4'-methyl-N (chloroacetamidomethyl) acetanilide.

2-chloro-2 ', 6'-diethyl-N- (3-alhoxypropionamidomethyl) -aeetanilid, Melting point 70.5 ° C.

2-chloro-2 ', 6'-diethyl-N- (2-chloroacetamidomethyl) acetanilide, melting point 153 to 159 "C 2-chloro-2 ', 6'-diethyl-N- (isobutyramidomethyl) -acetanilide, Melting point 130 to 133.5 C.

2-chloro-2'.6'-diethyl-N- (caprylamidomethyl) -acctanilide.

2-chloro-2 ', 6'-diethyl-N (fi-chloropropionamidomethyl) acetanilide, Melting point 133 to 136 "C.

2 chloro-2 ', 6'-diethyl-N- (propionamidomethyl) aceianilide, Melting point 144 to 146 "C.

2Chlor-2 ', 6'-diethyl-N- (butyiamidomethyl) -acctanilide, Melting point 122 to 123.5 "C.

2-chloro-2 ^l , b'-diithyl-N- (ureidmethyl) -acetanilide, melting point 206 "C.

2-chloro-2 ', 6'-diilhylN (iHMi / iimidomeihyl) acetanilide, Melting point I32 "C.

2-chloro-2 ', 6'-diilhyl-N (phenylacetiimidomethyl) -ncutun'iliil, Schmul / Punkt 135 bis I i7 "C".

2-Chloi'-2 ', 6'-diilthyl-N- (methacrylamid () · methyl) - iieetunilid, melting point 106 to 108.5 ¹ C.

2-C "hUir-2'-lort.-biiiyl-N- (v» lcriin> iikiinclhyl) -acetanilide.

. »■■>

methyl) -iicetiinilid, weiller I-Oststoff, cutting point 132 to IJ 3 " V. 2-Chlar-2 ', 6'-diilthylN- (2, J-dichloipropionnnmlonicihyO-ucciuniliil, because Jcr Keslsioff, melting point 154 to I%" (. '. 2-chloro-2'-methyl-6'-tert-btityl-N- (methacryli'imidomethylj-acetunilid, Sclimulzpunkt 158 to I6O, 5 ^U C. 2-chloro-2', 6'dimethyl-N- (itK'thacrylamidometlvyl) -acetunilid, white solid. Melting point 159.5 to 16O.5 "C. 2-chloro-2 ', J'-dimethyl-b'-lert.-biityl-N- (acetamidomethyl) -acetanilide, Melting point 163 to 165 ⁰ C.

(40) 2-bromo-2'-methyl-6'-tert.-butyl-N- (methacrylamidomethyl) acetanilide, white solid,

Melting point 151.5-154 ° C.

(41) 2-chloro-2 ', 6'-diethyl-N- (cyclopropanearboxamidomethyl) acetanilide. Melting point 179 to 180 ¹ C.

(42) 2-chloro-2 ', 6'-diethyl-N- (3-methoxypropionamidomethyl) -acetanilide, white solid, melting point 70.5 to 72.5 ° C.

(43) 2-Bromo-2'-ethyl-6'-tert, -butyl-N- (acetamidomethyl) -acetanilide,

Melting point 157.5 to 159.5 ° C.

(44) 2-chloro-2 \ 6'-diethyl-N- (acetamidoethyl) acetanilide,

Melting point 83 to 86 ° C.

(45) 2-chloro-2 ', 6'-diethyl-N- (2 ", 6" -dichlorobenzamidoethyl) -acetanilide.

(46) 2-chloro-2 ', 6'-diethyl-N- (3-butenainidoethyl) acetanilide.

(47) 2-chloro-2 ', 6'-diethyl-N- (formamidoethyl) acetanilide.

(48) 2-chloro-2 ', 6'-diethyl-N- (3-chloro-2-methylpropionamidoethyl) acetanilide.

(49) 2Chlor-2 ', 6'-diethyl-N- (acrylamidoethyl) -acetanilide.

(50) 2-chloro-2'-ethyl-6'-methyl-N- (cyclopropanecarboxamidoethyl) acetanilide.

(51) 2-chloro-2 ', 6'-diethyl-N- (cinnamon-urea-ethyl) -acetanilide.

(52) 2-chloro-2 ', 6'-diisopropyl-N (butyramidoethyl) acetanilide.

(53) 2-chloro-2 ', 6'-dimethyl-N- (succinimidomethyl) acetanilide.

(54) 2-Ch! Or-2 ', 6'-dimethyl-N- (sticcinimidoethyl) -acetanilide,

colorless granular solid, melting point 89 to 92 ° C.

(55) 2-Hrom-2'-ethyl-6'-methyl-N (succinimide () ethyl) acetanilide.

(56) 2-] od-2 ', 6'-diethyl-N- (succinimidk> methyl) · acctanilid.

(57) 2-13rom-2 ', 6'-diithyl-N- (succinimidomethyl) acctanilid.

(58) 2-Chloro-2 ', b'-diiithyl-N - [(2-pynoliiliiionl-yl) -iithyl] acetanilide.

(59) 2-chloro-N- (N-methylacetamide (i! »Thyl) -2 ', 6'-diethyl aeen \ nilkl.

(i> 0) 2-chloro-2 ' _l 6'-dittthyl-N- (N-methyl-dich! orbcn / .nmidomethyl) -ucctanili (l,

(61) 2-chloro-2 ', 6 ^l -diethyl-N (Nn \ ethyldichlorobene / amidoethyl) acetanilide.

(62) 2-chloro-2'.6'-dillthyl-N- {N-iUliyl-J-biUcnamidomethyl) acetanilide.

(hi) 2-chloro-2 ', 6'-diiHhyl-N- (N-methyl-3-butene-

amidoUthyO-acetnnilide.
(b4) 2-llrom-2 ', b'dimethyl-N- (N-mc: thylformat methyl) -acetam'lide.

(65) 2-ßrom-2'.6 '- (linieihyl-N (methylformamide llihyl) acetanilide.

(66) 2 - (.: chloro-2 \ 6 '- (liÜthyl-N- (N nielliylacrylami methylj-acotanilide.

(67) 2 ('chloro-2', b'-diethyl-N (N-iUhyl-I-lUhoxypropionamidomethyl I-Hcetnniliii

(68) 2-chloro-2'.b'-cliUthyl-N- (N-methyl - /]. ChloropropionamidomethyO-iicetanilide.

IS

(69) 2-chloro-2 ', 6'-diethyl-N- (N-propyl-propionamidomethyl) -acetanilide.

(70) 2-chloro-2'-methyl-6'-ethyl-N- (N-ethylacetamidoethyl) -acetanilide.

(71) 2-chloro-2 ', 6'-diethyl-N (isobutyryloxymethyl) acetanilide,

white solid,
Melting point 40 to 42.5 "C.

(72) 2-chloro-2 ', 6'-diethyl-N- (melhoxyacetoxymethyl) acetanilide,

white solid,
Melting point 66 to 68.5 ° C.

(73) 2-chloro-2 ', 6'-diethyl-N- (methacrylyloxymethyl) acetanilide,

white solid,
Melting point 48 to 52 ° C.

(74) 2-chloro-2 ', 6' -. Iethyl-N- (cinnamyloxymethyl) acetanilide,

white solid,

Melting point 68.5 to 72.5 ° C _.;

(75) 2-chloro-2 ', 6'-diisopropyl N- (butyryloxymethyl) acetanilide.

(76) 2-Bromo-2 ', 3', 6'-trimethyl-N- (acetc) xymethyl) acetanilide.

(77) 2-Chior-2 ', 6'-diethyl-N- (3-ethoxy- _; propionyloxymethylj-acetanilide,

brown viscous oil.

(78) 2-chloro-2 ', 6'-diethyl-N- (caprylyloxymethyl) acetanilide.

(79) 2-chloro-2 ', 6'-diethyl-N - (/ I-chloropropionyloxymethyl) -acctanilide.

(80) 2-ChloΓ-2 ', 6'-dimethylN- (propionyloxymcthylj-acctanilide,

Melting point 64 to 65 ° C.

(81) 2-chloro-2 ', 6'-dimethyl-N- (butyryloxymethyl) acianilide.

(82) 2 Chk) r-2 ', 6'-lert, -hutyl-6'-methyl-N- (acetoxymethyl) acetaniüd.

(83) 2-Chk> r-2 ', b'-diethyl-N- (carbamyloxyincihyl) -acctanilide.

(84) 2-chloro-2 ', b'-diethyl-N- (phenylaceU) xy

methyl) acctanilide.

(85) 2-Chk> r-2'.b'-diisopropyl-N- (methacrylyc> xymethylj-acetanilide.

(8b) 2-chloro-2'-tert-butyl-N- (valerykixymcihyO-acetanilide.

(87) 2-chloro-2'-methyl-6'-alhyl-N- (acetoxymethyl) acetanilide,

(88) 2-chloro-2 ', b'-diulhyl-N - (!. 2-dichk> i - - propionyloxymelhyl) ueetanilid.

(89) 2-Chk> r-2 \ b'-dimethyl-N- (methacrylyloxymethyl) -ucctunilide.

(90) 2-chloro-2'-methyl-b'-tcrt.-butyl-N- (mothacrylyc > xytnethyl) acctanilide.

(91) 2-chloro-2 ', 3'-dimethyl-b'-iert.-butyl N- (acetoxymethyl) succlanilide.

(92) 2 · ΙΐΓοιη-2'-ι »οΐΙψΙ-6'-Ιΰα-6υψΙ · Ν · (ι ^ ΐη-ucrylyl« xymethyl) -ncct «nilid.

(93) 2 '| oii-2', 6'-dittthyl-N- (t'yclopr »|) nncurbi) nyl oxymethyljacetimilide.

(94) 2-Chior-2 ', 6'-diatliyl-N - (; i-nicthoxy propionyloxymcthyO-aceUinilkl.

(95) ^2-Chüor-2-l .6' tlittlhyl-N- (uceU) xyUthyl) -acelUiiiilid.

(9b) 2-t: hk »r-2 ', b'-diiilhyl-N- (2", b "(lichlor ·

benzoyloxyllthylj-acctunilide.

(97) 2-Chloi - 2 ', b ^l -dilUliylN- (aciylyliixyilthy |) -HixMimi lid.

(98) 2-chloro-2 ', 6'-diethyl-N- (formyloxyethyl) -.

acetaniüd.

(99) 2-chloro-2 ', 6'-diethyl-N- (3-chloro-2-methylpropinoyloxyä thy I) - acetaniüd.

(100) 2-bromo-2 ', 6'-diethyl-N- (aerylyloxyethyl) acetanilide.

(101) 2-chloro-2'-ethyl-b'-methyl-N- (cyclopropanecarbonaloxyethyl) acetanilide.

(102) 2-chloro-2 ', 6'-diäihyl-N- (cinnamyloxyethyl)

acetaniüd.

(103) 2-chloro-2 ', 6'-diisopropyl-N- (butyryloxy-

ethyl) acetanilide.

(104) 2-chloro-2 ', 6'-diethyl-N- (tert-butyl acetoxymethylj-acetaniüd,
Melting point 64 to 69 "C.

(105) 2-chloro-2'.6'-diethyl-N- (ethoxypropionyloxymethyl) -acetanilide, fluid.

(106) 2-chloro-2 ', 6'-diethyl-N- (ethoxyacetoxymethyl) -acetaniüd,
Melting point 38 to 42 ° C.

(107) 2-chloro-2 ', 6'-diethyl-N- (hydroeinnamyloxy methylj-acet.inilid,

reddish viscous liquid.

(108) 2-chloro-2 ', 6'-diethyl-N- (3-mcihylerolonyloxymethyl) -acctanilide.

reddish viscous oil.

(104) 2-chloro-2 ', 6'-diethyl-N- (acctoxymethyl) acetaniüd, white solid, melting point 44 to 45 ° C.

ι (110) 2-bromo-b'-tert-butyl-N- (hydroxymethyl) o-acctotoluidid- (2,4-dichlorophenoxy) acetal,
Melting point 10b to 108 "C.

(111) 2-bromo-6'-ieri.-butyi-N (hydroxynieiii _i !) S o-acetotoluidid ^ .S-dichk'r-

3-nitrobenzoai,

Melting point 133.5 to 134.5 "C.

(112) 2-iirom-b'-teri.-lxiiyl-N- (hydroxyiiieihyl) -o-aectotüluidid-3-amino-2,5-dichlorobenzoai,

Melting point 12b to 129 C.

(113) 2-Bromo-6'-ated-butyl-N- (hydroxymelliyl) -o-aceU> li) luidiil- (2,4,5-lrichlorpheii () xy) accial,

Melting point 132 to 135 "C.

(114) 2-bromo-b'-tert-butyl-N- (hydruxymethyl) o-acctt) U) luidid-2, b-diclik) rben / .oat, SchiDcl / .punkt 133 to 139 "C.

(11 ^r >) 2 · Br () Πl ■ b '· terl-bιιtyl · N · (hydlΌxymelhyl) oacetotoluidid- (2-naphthyk> xy) acetal. Melting point 113 to 114 "C.

(116) 2-Bfom-b '- (ei't, -butyl-N- (hydi () xymethyl) o-acctotoluidid-pipcmnylat, melting point ISb ₁ S to 157.5 "C.

(117) 2-Ι1 | · υιιι · ^^ ι · Ι. ^ Μ, νΙ · Ν · (Ι) 5κΙπ ^ ηιοΐΙψΙ] o-acelotoluidid-l-naphthulinacetiil, resinous! - "liquid.

(118) b'-tert-Bulyl-2-ehloi-N- (hydroxymethyl) ο ncetotoluidid- (2,4-dichloipheiH) xy)

ι acetut.

Melting point 93 to 94 "C.

(119) 2-Bromo-2'-teri.-butyl-b'-Uthyl-N- (hydcox inethyl) -acetanilkl (2.4dichi <nplu! tioxy) acetal,

Melting point 82.7 to Hl ₁ O " C,

(120) b'-tcrt.-Butyl-N-ihydruxymethylJ ^ -jodoacct () loluidid- (2,4-dichloropheiU) xy)

lU'CUlt,

■ I "

• is

Melting point Π 0.5 to 111.5 ° Γ,

(121) 2-Bromo-6'-tert-butyl-N- (hydroxymethyl) -oacetotoluidide salicylate.
Melting point 139 to 140 ⁰ C.

(122) 2-chloro-2 ', o'-diethyl-N- (mercaptomethyl) -acetanilide-dimethyldithiocarbamate, Melting point 86 to 87 ° C.

(123) 2Chlor-2 ', 6'-diethyl-N- (hydroxymethyl) acetanilide picolinate,

light brown solid,
Melting point 106 to 108 ⁰ C.

(124) 2-chloro-2 ', 6'-diethyl-N- (hydroxymethyl) acetanilide nicotinate,
pitch-dyed fabric,
Melting point 95 to 96 ° C.

(125) 2-chloro-2 ', 6'-diethyl-N- (hydroxymethyl) -acetanilide-isonicotinate,

brown, crystalline solid, melting point 95.5 to 96.5 ° C.

(126) 2-chloro-2 ', 6'-diethyl-N- (hydroxymethyl) -acetanilide-o-nitrobenzoate, Melting point 123 to 124 ° C.

(127) 2-chloro-2 ', 6'-diethyl-N- (hydroxymethyl) -acetanilide-m-nitrobenzoate, Melting point 90 to 91 ° C.

(128) 2-chloro-2 ', 6'-diethyl-N- (hydroxymethyl) -acetanilide-p-nitrobenzoate, Melting point 102 to 103 ° C.

(129) 2-chloro-2 ', 6'-diethyl N- (hydroxymethyl) acetanilide benzoate.

Melting point 120 to 122 ° C.

(130) 2-bromo-6'-tert.-butyl-N- (hydroxymethyl) -o-acetotoluidide ^ .S.ö-trichlorobenzoate, Syrup.

(131) 2-chloro-2 ', 6'-diethyl-N- (hydroxymethyl) acetanilide piperonylate,
Melting point 106 to 108 ° C.

(132) 2-Bromo-6'-tert-butyI-N- (hydroxymethyl) -o-acetotoluidide benzoate.
Melting point 98 to 99 ° C.

■ ss

40

In order to illustrate the advantages of the present invention, evaluations of the herbicidal pre-emergence properties were made of the haloacetanilide derivatives according to the invention determined in greenhouse studies. In each case, a specific number of seeds from a number of different plants, from each of which represents a botanical species, planted in greenhouse trays.

Good quality soil was placed in aluminum pans and to a depth of 9.5 to 12.5 mm from the The top of the seed tray is compressed. A predetermined soil was then placed on the ground prepared in this way Number of seeds of the different plant species applied. The one for filling the bowls evenly Required soil was after sowing in a Dish weighed with a known amount of active ingredient incorporated in a solvent or as wettable Powder was mixed with the soil thoroughly and used as a cover for the sown trays. The trays were then placed in a greenhouse basin, where they were removed from below as needed for a sufficient moisture for germination and growth has been watered.

About 14 days after sowing and treating, the plants were observed and the results held. The herbicidal rating was obtained using a fixed scale that points to the average percentage Germination from each seed lot based. The ratings are explained as follows:

0 = no herbicidal activity.

1 = Slight herbicidal activity.

2 = Moderate herbicidal activity.

3 = Strong herbicidal activity.

The herbicidal pre-emergence effectiveness of the Λ-haloacetanilides is in the following table for the various application conditions and for Surface applications as well as when being placed in the ground.

In the tables below, the letter "M" following the application ratio indicates that the herbicide was introduced into the soil. A "-" instead of a number means that with the respective Application ratio no experiment has been carried out for this plant.

The different seedlings are identified by the following letters:

A = soybean

B = sugar beet

C = wheat

D = rice

E = sorghum

F = burdock (common)

G = wild buckwheat

H = funnel winch

I = hemp sesbania

J = white goosefoot

K = Cissampelos pareira

L = Bromus Tectorum

M = panicum spp.

N = chicken millet

O = finger millet

(Digitaria sanguinalis)

Table 1

Vcr- Anvvcn- plant species

binding

(Jung behaves- Λ H C

from nis

I)

example (kg / ha) *) 0 1 0 2 3 0 0 1 0 0 1 3 3 3 3 1 V 1 0 2 2 3 0 0 0 0 0 1 3 3 3 3 2 IVM 0 1 2 () 2 0 1 (I. 2 0 0 3 2 3 3 d IV

J.

Foilsct / unu

Ver To whom- PHan / enarten 1 B. C. D. ι ·: - ■ 1 Il I. 1 J 2 K 1 L. 3 M. N O am
manure manic
decay Λ 0 I · ' G 0 0 0 0 0 from nis 0 0 2 1 0 2 example (kg / ha) *) 0 0 3 3 3 1 0 0 0 0 2 3 3 3 5 IVM 0 0 0 0 0 0 0 0 0 0 0 0 2 3 1 6th IV i 2 0 2 3 1 0 0 0 2 0 1 3 3 2 7th IV 0 0 0 0 3 1 0 1 1 0 0 0 3 3 3 8th Il 0 0 0 0 0 0 0 1 2 0 0 2 - * 3 0 I. 0 _ I. I. 0 2 0 0 2 3 0 0 1 3 3 K) (V 0 1 0 0 0 0 0 0 1 0 0 2 ■ 1 2 2 Il 0 0 0 0 2 0 0 0 2 1 0 0 2 3 3 U IV 0 1 0 1 0 0 0 0 1 0 0 0 1 3 3 H 0 0 1 3 2 0 0 0 0 0 0 2 3 3 3 IVM 0 0 1 0 0 0 2 0 0 1 0 I. 3 3 3 12th Il 1 0 0 0 0 0 2 0 1 3 1 1 3 3 2 I. 0 0 0 0 1 0 2 1 2 3 0 0 2 3 3 14th IV 0 1 0 0 2 0 1 0 2 2 0 2 1 3 1 15th IV 0 1 0 1 1 3 0 0 3 2 0 3 2 3 3 16 IV 0 0 0 0 0 0 0 0 1 2 0 3 1 2 2 17th IV 0 2 2 1 2 0 0 1 1 0 0 ! 2 3 3 18th IV 0 2 ·) 3 2 0 0 0 1 0 0 3 3 3 3 23 IV 0 0 2 3 2 0 0 0 2 3 0 3 3 3 3 AROUND 1 0 0 1 1 0 1 0 1 2 0 3 2 3 2 25th IV 0 0 0 3 3 0 0 0 1 0 0 0 3 3 3 27 IV 0 3 3 3 3 0 1 1 2 3 0 3 3 3 3 28 IV 0 1 3 2 3 0 0 0 1 2 0 2 3 3 3 29 IV 0 1 '.) 0 0 0 2 0 0 1 0 2 0 3 1 30th IVM 0 2 1 3 3 0 0 0 1 0 0 3 3 3 3 35 IV 1 1 0 2 2 0 0 0 0 0 1 0 3 3 3 36 IV 1 2 0 1 1 0 (J 0 1 0 1 3 2 3 3 37 IV 1 0 1 1 0 0 0 0 0 0 0 0 3 3 3 Il I. 0 0 0 1 0 0 1 I. 0 0 1 2 3 3 38 IVM 0 1 i 1 3 0 1 2 1 0 Ü 2 2 3 3 39 IVM 0 0 0 0 1 0 1 1 1 0 0 3 1 3 2 40 IVM 0 1 I, 1 3 0 0 2 2 I. 0 1 3 3 3 41 IVM 0 0 0 2 1 0 0 1 0 1 0 1 3 3 3 42 IVM 0 0 I. 1 3 0 0 0 0 0 0 0 3 3 3 43 IVM 1 0 0 0 3 0 2 0 I. Λ
J) 2 2 3 3 3 II 0 0 0 1 0 0 2 0 I. 2 0 I) 1 3 3 44 IVM 0 0 0 0 1 0 -) 0 0 I. 1 2 1 3 3 II 0 1 0 0 1 0 U 0 0 I. 0 3 2 3 ~ M IV 2 3 0 1 0 0 1 0 3 3 0 2 2 3 2 74 IV 0 0 0 0 I. 0 0 0 0 1 0 0 2 3 3 7> IV 0 0 0 0 0 0 0 0 0 ] 0 0 2 3 2 7o IV 0 2 0 0 2 0 I. 1 2 1 0 2 > 1 2 107 IV 1 I. 0 0 0 0 0 0 1 0 3 - 3 1 108 IV 1 0 0 0 I. 0 3 1 109 IV 1 I. 1 I. 0 0 2 3 3 111 IV 0 ; i 3 ■) 0 0 3 3 112 IV 0

continuation

Ver Anvven- Plant species am manic manure behaves- A B C D E I- (ί from nis example (kg / ha) *)

V
IV

*) Application ratio (kg / ha)

I = 0.562

II = 0.281
Iv = 1.125
V = 5.625

The figures in the preceding table clearly show that the compounds of the present Invention effective herbicides are and are particularly valuable properties for the control of fine-leaved and grassy weeds even in the presence of Gramineae crops.

The post-emergence herbicidal activity of the various compounds of this invention is demonstrated shown. The active ingredients were sprayed onto 28-day-old samples of the various plant species. The spray, an acetone / water solution containing the active ingredient and a surfactant

Table H.

(35 parts of the butylamine salt of dodecylbenzenesulfonic acid and 65 parts of tall oil, condensed with ethylene oxide in Ratio of Ii mole of ethylene oxide to 1 mole of tall oil) is used in different plants Tray sets used with different application ratios of the active ingredient. The treated Plants are placed in a greenhouse, the effects observed, and after approximately 14 days held.

The herbicidal emergence potency index used in the table below is as follows Are defined:

Reaction of the plant

index

No harm
Slight damage
Moderate damage
Severe damage
Killed

The plant species used in these experiments are identified by the following letters:

A = funnel winch

B = wild oats

C = bluegrass

D = ryegrass

E = radish

F = sugar beet

G = cotton

Table ul

Herbicide post-emergence effectiveness

H = corn

I = foxtail grass

1 = chicken millet

K = finger millet

L = amaranth

4> M = soybean

N = Wilder Buchweise

O = tomatoes

P = sorghum

Q = rice

link

example

Application ver
ratio

(kg / ha) *)

PLANT ONLY

Λ 15 C Π

M N

ΠΙ

πι

IV
IV

0 0 4 4

114 4

0 0 4 4

0 14 4

1 3

Ji 3

4th 4th 4th 4th 2 4th 4th 3 4th 2 4th 4th 4th 4th 0 4th 3 4th 4th I.

fniliinsinverh; illnis

As shown in Table IV below, typical compounds are opposed to the present invention the commercially extremely successful herbicide "Ramrod" (registered trademark of the company Monsanto Co.) superior. The active component of the herbicide »Ramrod« is N-isopropyl-2-chloroacetanilide, which is generally referred to as "propachlor". If you consider the in the present description using the rating scale indicated for table I for the relative herbicidal activity, one can ι ο recognize that the compounds according to the invention examined do not damage the valuable cereal plants, Soybeans and rice effect while using them at the same time; keep the weeds under control egg. H. moderate to severe damage to the offending ι .s Bromgrass weeds that grow up with the crops. In contrast to this, it echoes commercial herbicide »Ramrod« when using comparable application ratios in the amount of 0.28 kg / ha and 1.12 kg / ha does not control the bromine grass and also damages the Rice. Even if the herbicide "Ramrod" does not damage soybeans, it can cause bromine grass to grow so that it flourishes collectively, not prevent it.

25th

Table IV

Herbicide pre-emergence effectiveness

link relationship soy rice Bram- U from example beans grass No. (kg / ha) 4th 1.12 0 0 3 8th 0.28 0 0 2 14th 1.12 0 0 2 70 1.12 0 0 2 Propachlor *) 1.12 0 2 0 0.28 0 1 0

*) Active ingredient (N-isopropyl-2-chloroacctanilide) in "Rarnrod" ilcrbicide.

The herbicidal preparations of this invention include concentrates that require dilution before Make use necessary, with at least one active ingredient and an auxiliary in liquid or solid form included. The preparations are produced by the fact that the active ingredient with a Additives such as a diluent, extender, carrier and conditioning agent mixes to form preparations in the form of finely divided particulate solids, granules, pellets, solutions, dispersions or to create emulsions. It can therefore take the active ingredient together with an aid such as a finely divided solid, a liquid of organic origin, water, a wetting agent, a dispersing agent, an emulsifying agent or any combination of these agents can be used

The preparations of this invention, especially liquids and wettable powders, preferably contain as Konditionicrmittcl one or more surface-active agents in such amounts that one given preparation is easily dispersible in water or in oil. The introduction of a surfactant Means in the preparations increases their effectiveness significantly. The designation »gren / fl ·

45 " active agents" includes, inter alia, wetting agents, dispersants, suspending agents or emulsifying agents. Anionic, canonical and nonionic agents can also be used with good success.

The preferred wetting agents are alkylbenzene and alkylnaphthalene sulfonates, sulfated fatty alcohols and amines or acid amides, long-chain acid esters of sodium isoethionate, esters of sodium sulfone succinate, sulfated or sulfonated fatty acid esters, peirolsulfonates, sulfonated vegetable oils, ditertiary acetylic glycols, polyoxyethylene derivatives of alkylphenols (especially isooctylphenol and nonylphenol) or polyoxyethylene derivatives of the mono-higher fatty acid esters of hexitol anhydrides (e.g. sorbites). Preferred dispersants are methyl cellulose, polyvinyl alcohol, Sodium lignosulfonates, polymeric alkylnaphthalene sulfonates, sodium naphthalene sulfonate and / or polymethylene bisnaphthalene sulfonate.

Wettable powders are water-dispersible preparations that contain one or more active ingredients in one contain inert solid extenders and one or more wetting and dispersing agents. The inert solid Extenders are usually of mineral origin, such as natural clays, diatomaceous earth, and synthetic ones Minerals derived from silica and the like. Examples of such extenders are Kaolinite, attapulgite clay and synthetic magnesium silicate. The wettable powder preparations of these Invention usually contain about 5 to about 95 parts of active ingredient, about 0.25 to 25 parts of wetting agent, about 0.25 to 25 parts dispersant and 4.5 to about 94.5 parts inert solid extender, wherein all parts are based on the weight of the total preparation. If desired, about 0.1 up to 2.0 parts solid inert extender with a corrosion inhibitor or an antifoam agent or both replaces willow.

Aqueous suspensions can be prepared by having an aqueous slurry of water-insoluble active ingredient mixed together in the presence of dispersants and grinds to a to obtain concentrated slurries of very finely divided particles. The concentrated aqueous Suspension has an extremely small particle size, so that when diluted and sprayed the coverage is great takes place uniformly.

Emulsifiable oils are usually solutions of the active ingredient in water that cannot be mixed with water or partially water-miscible solvents, together with a surfactant. to Suitable solvents for the active ingredients of this invention include hydrocarbons and water immiscible ethers, esters or ketones. The emulsifiable oil preparations generally contain from about 5 to 95 parts of active ingredient, about 1 to 50 parts of surfactant, and about 4 to 94 parts of solvent, all parts by weight and based on the total weight of the emulsifiable oil are related.

Granules are physically stable, particulate preparations containing the active ingredient, the Active ingredient based on a matrix of an inert, finely divided particulate extender is liable or distributed. To help leach the active ingredient from the particulate matrix, may include a surfactant as previously indicated in the formulation to be available. Natural clays, pyrophyllites, lllit and

Vermiculite are examples of useful particulate mineral extenders. The preferred extenders are porous, absorptive, preformed particles, like preformed and sifted particulate attapulgite or heat expanded particulate> Vermiculite and the finely divided clays such as kaolin clays, hydrated attapulgite or bentonite clays. For education herbicidal granules, these extenders are sprayed onto the active ingredient or mixed with it.

The granule preparations of this invention enihai- id th about 5 to about 30 parts by weight of active ingredient per 100 parts by weight of clay and 0 to about 5 parts by weight surfactant per 100 parts by weight of particulate clay. The preferred granular formulations contain about 10 to about 25 parts by weight of active ingredient per 100 parts by weight of clay.

The preparations of this invention can also contain other additives, such as fertilizers, Contain herbicides and other pesticides that are used as an aid or together with any of the auxiliaries described above can be used. To connections that go to the Combination with the active ingredients of this invention are suitable include, for example, triazines, ureas, Carbamates, acetamides, acetanilides, uracils, acetic acids, phenols, thiocarbamates, triazoles, benzoic acids and nitriles. Other useful aggregates include materials in which plants Put down roots and grow like compost, manure, humus and sand.

In operating in accordance with the present invention, effective amounts will be those of the present invention Haloacetanilide applied to the plants or used in the soil containing the plants or in incorporated into the aqueous medium in any suitable manner. The use of liquid and particulate solid preparations on plants or on the ground can be prepared using conventional Procedures, for example power atomizers, tree and hand sprayers and spray atomizers, take place. The: Because of their effectiveness, preparations can also be taken from airplanes in low doses Dust or spray are applied. The use of the herbicidal preparations in aquatic plants is usually carried out in such a way that the preparations are added to the aqueous medium admits the place where one wishes to control the aquatic plants.

The invention of an effective amount of the compounds of this invention on the plant is essential and decisive for the herbicidal effect of the preparations according to the invention. The exact The amount of active ingredient to be used depends on various factors, such as the plant species and the stage of development, the type of soil and the soil conditions, the amount of rain and the specific, used haloacetanilide derivative according to the invention. In the case of non-selective pre-emergence treatment the compounds of this invention are usually used in proportions of 1 to 30 kg / ha. To the selective pre-emergence use for plants or Börf ^ n will usually dosages of 0.052 to 5,650 kg / ha used. In some cases, lower or higher application ratios may be required be. However, from this description, including the examples, the person skilled in the art can by means of simple Easily try to determine the optimal ratio to use for any particular case.

The term "soil" is used here in its broadest sense and includes all conventional ones "Soils" as used in "Webster's New International Dictionary," Second Edition, Unabridged (1961). This term therefore refers to any substance or medium in which plants can take root and grow, and not just the soil as such, but rather as well as compost, fertilizers, manure, humus and sand that are suitable for supporting vegetation.

709 536/1

Claims (1)

Patent claims: 1. Haloacetanilide derivatives of the general formula Il R C-CH ₁ X R (CHt) ,, A C R '