DE2226593C3 - Haloacetanilide derivatives and herbicidal preparations containing them - Google Patents

Description

wherein

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

Y means oxygen or is sulfur, if A is sulfur Kr,

R lower alkyl and

R 'are hydrogen or lower alkyl and can be the same or different,

R- is hydrogen or methyl,

R 'is hydrogen, lower alkyl, lower dialkylamino. lower alkenyl, lower alkoxyalkyl, lower haloalkyl, cyclopropyl, aryl, 2-hydroxyphenyl, Aryloxyalkyl, llalogenaryl, haloge naryloxyalkyl, arylalkyl, arylalkenyl, nitroaryl, lljlogennitrophenyl, 2-pyridyl, J-pyridyl, 4-pyridyl. 3,4-methylenedioxyphenyl. Amino, haloamino-phenyl is,

K 'is lower alkyl or R' and R ⁴ are connected to one another to form an alkylene bridge with 2 or 3 carbon atoms,

X is chlorine, bromine or | od and

η has the value I or 2 and m has the value O, or the value I besil / t if R 'and R ⁴ are linked to form an alkylene bridge with 2 carbon atoms.

2. Herbicide /.Überilung, characterized by ilen Ciehalt on a compound of claim I and a customary aid.

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

The halogen acctanil derivatives according to the invention have the general formula

O
! I
RC (I IA

K ll, i "Λ (R '

Λ -Nil. -N (CO) R ¹ . S, mn stoll or Si luve

IcI im.
Y S.iiii-rstc'il is heilcutel or sulfur. if A Si hu efel .m.

R lower alkyl and

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

R- is hydrogen or methyl,

R ^{1 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, 4-pyridyl, J- -Pyridyl, 3,4-methylenedioxyphenyl, amino, halo-aminophenyl,

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

X is chlorine, bromine or iodine and

η has the value of I or 2 and m has the value C, or has the value 1, if R '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 Substiluents of the general formula given above, for example, have the following meanings to have:

R methyl, ethyl, propyl, isopropyl, n-butyl, primary Isobutyl, secondary isobutyl, tertiary butyl. n-amyl, branched-chain amyls, the normal and branched hexyls, hcptyls, octyls, nonyls and dccyls.

R ^{1 is} hydrogen, methyl, ethyl, propyl, isopropyl, η-butyl, primary isobutyl, secondary isobutyl, tertiary butyl, n-amyl, branched-chain amyls, the normal unc-branched hexyls, Mcptylc, Oelyles, Nonyls and Decyls.

R ^{1 is} hydrogen, methyl. Ethyl, propyl, isopropyl, n-bulyl, primary isobutyl, secondary isobutyl, tertiary butyl, the normal and branched amyls, henyls, heplyls, octyls, nonyls, decyls. Chloromelhyl, bromopropyl, iodobutyl, fluorohexyl, the alkenyl and alkoxyalkyl groups, which correspond to the alkyl groups mentioned above. Phenyl. ToIyI, Niiphthyl. Benzyl or phenoxyalkyl.

R 'The alkyl groups of R ¹ .

Preferred halogenicetiinilide 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> NHCi group and n is the Wurt I. wiTi'en means «; a ( 'iirbnniiiminniMi-Ke ■ iktion a 2 I lylogen-N- (substituted-melhylj acetaiulids with a Mitril or an inorganic cyanide under acidic prepared inventions Bed. I) ie llalogcnacetu ml ic I Deriv.iti ¹ of the present I jiindiiiig. where η is the value I ifwrist and Λ is oxygen or sulfur. are prepared in a similar manner, for which a 2 liters of N (mi'islilinertes methvl) -acetanilid in a monocarntisautc ¹ iiinset / t endi.'ii c (ini | i | ie be, the / iir formation of a

Carbonium ions is suitable and can easily be displaced or replaced under acidic conditions. Thus, the starting material can be a 2-halo-N-methylacetanilide in which the methyl group is substituted with a halogen atom, an alkoxy, alkylthio, hydroxy, 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 nitrite 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 starting material in these reactions is the adduct of a haloacetic acid derivative, such as the halide or anhydride, with a 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 is the> NH group;:; and η has the value 1 can also be prepared by reacting a nitrile with an iX-halo-disubstituted-N- (alko, '(ymethyl) -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 I, are prepared by combining a substituted methylene arylamine with an appropriately substituted amide or imide Formation of the corresponding N- (anilinomethyl) -amide or -imide produces. The amide or imide intermediate is then haloacetylated with a haloacctyl halide to form the compounds of interest.

The haloacetanilide derivatives of the present invention, in which A denotes the> NH group and η has the value 2, are easily prepared by chloroacetylation of N- (substituted phenyl) -N'-acyl-ethylenediamine. The haloetanilide derivatives of the present invention, wherein A is the group N- (CN = O) ,,, - R ⁴ and m is O or I, are prepared in a similar manner by haloacetylation of an N- (substituted phenyl) -N '-acyl-N' - (C = O), "- R ^l ethylenediamine produced. The ethylenediamine derivatives that use as starting materials for such reactions! can easily be prepared in a conventional manner by reacting a substituted aniline with alkyl ring agents such as an N- (2-fluorohyl) alkyl amide. N-2- (hydroxyethyl) alkylamide. N- (2-ltromethyl) -phihalamide or N-acyla / iridine alkylated.

The novel compounds of the present invention, A is oxygen wiirin ndrr sulfur and η the Wen 1 hesit / l. are easily produced by 1.1 using an N- {Mibsliluierlen Phenvh-Ethvlester der allucmci

a formula

R ²

; -NFI-CH, CH, -O CR ¹

R ¹

in which the radicals R, R ¹ , R- and R ^{1 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) ethylsier.

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'-diethy <:> henyl) -acetamidon-kihylchloracetat. 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 _n HIiNCL ₂ O ₁ :

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 an appropriate 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 thus obtained was recrystallized from methanol and had a melting point of 148 to 149 ° C. Analysis for CiH ₂ ICINiO ₂ :

Calculated: C 60.7. H 7.13%;

found: C 60.68, 117.22%.

Example 3

This example describes the preparation of 2-chloro-2 ', 6'-diethyl-N- (2 ", b" -dichlorobenzamidomethyl) -acetanilide. About 100 parts of 2-chloro-N-chloromethyl-2 ', 6'-diethyl-acetiinilid were / ti about i ^r) () parts sulfuric acid in a suitable Reaklionsge fäß added, cooled to O'C and stirred / u this mixture was added 2.6-dichlorophenyl nitrile was slowly added about b7 files. When the addition of the Nilril was complete, the reaction mixture was approximately I. heated ^r> hours with constant stirring to about 75'C. The reaction mixture was then poured into ice water and a light brown dye precipitated. This was done by! '' Titration

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

Calculated: C 56.16, 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-Hd. 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 crystallization from isopropanol, the product had a melting point of 121.5 to 123.5 ° C. Analysis for Ci ₇ H ₂ ICIN ₂ O ₂ :

Calculated: C 63.25, H 7.18%;

found: C 62.38. H 6.95%.

Example 5

This example describes the preparation of 2-chloro-2 ', 6'-diethyl-N- (formamidomeihyl) -acctanilide. About 200 parts of 2-chloro-N-chloromethyl-2 ', 6'-diethyl acetanilide were added to 400 parts of concentrated sulfuric acid. The mixture was cooled to approximately 10 ° C. Added 70 parts of sodium cyanide and heated to about 50 ° C. As a result of the exothermic reaction, the temperature of the reaction mixture rose to approximately 85 ° 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 crystallized first from ether and then from a mixture of methylcyclohexane / toluene; Melting point 85 to 89 "C. AtIaIySCfUrC ₁₄ Hi ₁ ) CIN ₂ O ₂ :

Calculated: C 59.46, H 6.77%;

found: C 59.64, H 6.69%.

Example 6

This example describes the preparation of 2 ^{-chloro-2 ', 6 r} -diethy) -N- (3-chloro-2-methylpropionamidomethyl) aeetanilide. About 100 parts of 2-chloro-N-chlormctnyl-2'.6'-diäthylacetanilid were mixed with 26 parts of methacrylonitrile, and added in a suitable reaction vessel to about 350 parts of sulfuric acid at a temperature of about 10 ^J C. The reaction mixture was heated to about 65 "C for about 4 hours while bubbling dry hydrogen chloride. The reaction mixture was then poured into ice water and filtered to remove the precipitate, which was then crystallized from isopropanol.
Analysis for C _1; l I ₂₄ CbN ₂ O ..:

Calculated: C 56.83. H 6.73%;

found: C 56.85. Il 6.62%.

Example 7

This example describes the preparation of 2 clic ( 'Hloi "-2', 6'-diäthyi N- (acrylamidomethyl) acetanilide. About I Vi parts of 2-Clilor-2'.6'-diälhyl-N-rncthoxyuu'thvlai'ctiinilid was mixed with about 27 parts of acrylonitrile and about 3 (X) parts of sulfuric acid was added, the reaction mixture was then warmed to about 55 ° C and held at that temperature for about 1 hour, followed by pouring into ice water to give a solid granular precipitate , which was separated off by filtration, washed with water and recrystallized from isopropanol. The recrystallized material had a melting point of 174 to 175 "(J. Analysis for Ci ₆ H ₂ ICIN 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- (cyciopropanecarboxamidomethyl) acetanilide. About 300 parts of concentrated sulfuric acid were placed in a suitable reaction vessel and cooled to about 0 ° C. with a stirrer. Then ungelähr IOC Ί of 2-chloro-2'-ethyl-ö'-methyl-N-chloromethyl acetanilide were added slowly and the mixture rush to about 25 'C ¹ heated to the solution to accelerate the adduct. The mixture was ^: ·: cooled again to about 10 ° C. and then about 28 parts of cyclopropylnitrile 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 I.iswaiser. 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 crystallized from isopropanol: melting point 154 to 156.5 ° C.

Example 9

Preliminary stage for example 10

N- (2,6-diethylanilinomethyl) -N-methyl acetamide

Il

C CH ₁

NH CiI, N

C ₂ II ₅

In a suitable reaction vessel were approx 100 parts of N-methylacelamide introduced and approximately 100 parts of 2% sodium methoxide suspension in dimethylformamide admitted.

With the exothermic reaction, the temperature rose of the reaction mixture from about 24 to about 30 "C. Then about 160 parts of 2,6-diethyl-N-methylene-1 in was added, causing the temperature to rise further to approximately 44 "C. The reaction mixture was stirred at this temperature for approximately 7 hours held- After stirring was stopped, the mixture cooled to room temperature after approximately 16 hours away. About 3 parts of acetic acid were then added, followed by about 200 parts of water and stir the mixture vigorously. There were approximately 150 parts of Ben / οι in support of the separation of the Mixture in cine oil and a layer of water added. The water layer was discarded and the Oil layer with another 200 parts of water, the I part. Acetic acid contained, washed. iib'T Miignesiiinisulf.it

dried 11 ml distilled in Viikiiiiin Müh ei held cmc straw-colored liquid. du- ills N (2.6 l) ialli \ l, iniliiH> methyl) N mellivlacetaiiiui idcntifi / icii ttiiuie
Analysis for C,, M .... N..O:

Calculated: (71.75. 119.46. N W.IVVn;

found: (71.40, 119.54, N 12.05%.

2- (

Il ei> .pii I IO

Ιοι N- (N-IiRMlIvIiH li.iinidometh \ I)
2'.6'-diüllivl; icelanilid

(, IL

(Ml;

C (TL (T

(Tl, \ CC
(Tl,

Approximately 72 parts of N- (2,6-Diiiyliinilinotnethyl) -N -methylacctamid. that is obtained by the method m in Example 9 reverberates ¹ , were dissolved in about 1 (K) ^ toluene, placed in a suitable Kcaktionsgefold and added about 40 parts of 2,6-l.utidine. The mixture was mil carbon dioxide / AciMon and quenched under vigorous stirring, about 40 parts ( "hloracclylchlorid added over 15 minutes in 70 parts of benzene, wherein the temperature of Keaklionsgcmisches / wipe was 20 th and -30 ⁰ C supported. It lieli the Kcaklionsgcmisch Then about 100 parts of water were added and the mixture was separated into an oily traction and an aqueous fraction, the aqueous fraction was discarded and the oily traction twice with 150 liters of water at a temperature of about 35 ° C. The reaction mixture was then evaporated to practically dryness in vacuo and / and first 100 parts of methylcyclohexane and then about 15 parts of benzene were added to the residue to form a homogeneous solution the liquid phase separated by filtration, with a mixture of methyl c \ dohcxan / Benzoi and then dried in the air. After recrystallization from a mixture of benzene and oil, a cream-colored product with a melting point of 82 to 83 ^° C. was obtained.

Calculated: C 61.83. H 7.46. CM 1.41, N 9.01%;

found: C 61.68. H 7.47. Cl 11.48, N 8.97%.

Example 11

2-chloro-2'.6'-diethyl-N- (r.uccinimidomethy!) - acelanilide

CML

C CH, Cl

CH- N

O C

CH,

Dimethylformamide were heated in a suitable reaction vessel at a temperature of between 90 and 95 ° C. for hours. The reaction mixture was then evaporated in vacuo, giving a residue which complied with N (2.6l) iälhvlanilinome Ihyl) siiccininud The residue was dissolved in unfilled parts and immediately added 2.6-1.iilidine. The mixture was cooled to about 10 ° C. and about 21 parts tiloracclyl chloride was added in portions over the course of 20 minutes, the temperature of the reaction mixture being kept between about 10 and 5 ° C. A heavy precipitate fell out. The reaction mixture then absorbed Cooled to about 0 ° C. Maintained at this temperature for 1 hour and then the precipitate from the dark red veneer was deposited in dilute hydrochloric acid. Washed water and toluene, then recrystallized from a methacrylate / ethic acid (icmisch recrystallized, whereby a gray powder with a melting point 146 to 147 C was kept.
Aruilvsc For (M- (TN-O ₁

Calculated: C 60.62. 116.28. (110.53. N 8.32 "/«:
found: C 60.M0. H 6.25. (110.53. N H.25%.

Example 12

2 chlorine -2 .6 -di; itli \ iN - [(2pvirolidinoii I \ l)
methylj-aceianilide

CIL

(ML

C (H (I
NO

CII, NC (TI
ILC dl.

F. in a mixture of about 10 parts of 2,6-diethyl-N-methynaniline. 20 parts of suceinimide and 75 parts. About 40 parts of N- (2,6-diethylanilinomcthvl) -2 · pyrrolidinone were dissolved in about 100 parts of toluene, and about 30 parts of 2,6-l.utidine were added to the solution. .. The mixture was then cooled with constant stirring at about -30 "C Approximately 2> parts of chloroacetyl chloride dissolved in about 80 parts of toluene were added over 15 minutes keeping the temperature between -20 and - 30 ⁰ C was maintained 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 and an aqueous fraction formed. The latter was discarded and the remaining oil washed with water and vacuum stripped. The oily residue was dissolved in a mixture of 100 parts of methylcyclohexane and 20 parts of benzene. The product which precipitated from this mixture on standing was obtained after recrystallization from a mixture of methylcyclohexane / benzene in the form of colorless granules: melting point 56 to 57 ° C.
Analysis for Ci7H: iCIN _; Oj:

Calculated: C63.25. H 7.18. Cl 10.98%;

Found: C 63.36. H 7.33. CM 1.02%.

Example ii

Vorlufi "IVi r i'rlindungsgt'inalli · connections

N (2.h-l) iaih \ lamlinoniethyl) N.N'-irimclhyloxamide

CII,

CJ I,

C [I, N C C

CII,

Approximately 650 parts Ν, Ν ', Ν'-trinielliyloxamide and approximately 4 parts of potassium hydroxide pellets were placed in a suitable reaction vessel, approximately HOO Parts of 2,6-diethylphenylazomethine and then about 5 parts of a 25% solution of sodium methoxide added in methanol. The reaction started slowly, with the temperature increasing in 15 minutes Room temperature rose to about 50 ° C and then dropped to about 45'C. The mixture then became heated with constant stirring to about K) OC and then to room temperature (about 2JC) let cool down. The honey-like syrup obtained, the small amounts of unreacted potassium hydroxide pellets was dissolved in 25 (K) 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 is filtered and twice with 1200 parts of methylcyclohexane were washed. Finally, the product was washed three times with 1500 parts of water and on the Air dried: Melting point 7 3 to 7 3.3 C. Analysis for C, J I. -, N, C).,:

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

These and other compounds that have two adjacent carbonyl groups can easily haloacetylated to form compounds of the present invention in which π is 1 will.

Example 14

This example describes the preparation of 2-chloro-2 ', 6'-diethyl-N (propionyloxymelhyl) acetanilide. About 140 parts of 2-chloro-2 ', 6'-diethyl-N-chloromethylacetanilide dissolved in tetrahydrofuran was placed in a suitable reaction vessel and a solution of about 40 parts of propionic acid in tetrahydrofuran was added. After the mixture was essentially homogeneous, approximately 55 parts of triethylamine were added in portions. The solution was then heated to reflux temperature, refluxed for approximately 3 hours, and then cooled to room temperature. The resulting precipitate was separated off by filtration, taken up in diethyl ether, and the ethereal solution was washed with aqueous sodium bicarbonate solution, then with water and dried over magnesium sulfate. The solution was then stripped off in vacuo and the oily residue obtained was crystallized after solidification from hexane. A white solid with a melting point of 64 to 65 ° C. was obtained. Analysis for CIbH ₂₂ CINO ₁ :
Calculated: C 61.63, H 7.11%;
found: C 61.94, H 7.04%.

K)

Example I. >

This example describes the preparation of 2 chloro-2'.h 'ili; ithyl N (forinyloxyineihyl) acclanilide. About 140 parts of 2 (hloi 2 ', 6'-diethyl N chlorine ihylacetanilide, dissolved in tetrahydrofuran, was placed in a suitable reaction vessel) and about 2' parts per cent of formic acid and 50 'parts of iriethylamine were added. The reaction mixture was then refluxed for approximately 5 hours and cooled to room temperature. The tetrahydrofuran was stripped from the gemstone by vacuum distillation, the residue was dissolved in diethyl ether, and the ethereal solution was first mixed with aqueous sodium bicarbonate. then washed with water and finally dried over magnesium sulfate. Distillation of the ethereal solution in vacuo at 65 × 75 torr gave a clear, oily liquid.
Analysis for C ₁ ! 1,, CINO ₁ :

Calculated: C 59.26. 116.1'Wi;

found: C 54.32. H 6.47 "/».

Example 16

This example describes the preparation of 2-chloro-2'.6'-cliathylN (butyryloxymethyl) aceianilide. About 200 parts of 2C chloro-2 ', 6'diäihyl-N-chloromethylacetanilid, dissolved in tetrahydrofuran, were placed in a suitable reaction vessel, stirred well and about 70 parts of n-butyric acid and about 80 parts of triethylamine were added in portions with continued stirring. The reaction mixture was refluxed for approximately hours, cooled to room temperature, filtered and the filtrate stripped by vacuum distillation. The residue was dissolved in diethyl ether, washed with aqueous sodium bicarbonate, then with water and washed over magnesium sulfi. dried. The magnesium sulfate was removed by filtration and the solvent ^{stripped off by 1} distillation at 60 ° C / l Torr. The residue obtained was a red-orange-colored oil.
Analysis for Cl _n H ₂₁ CINO ,:

Calculated C 62.66, H 7.42%;

found: C 63.01, H 7.7 3%.

Example 17

This example describes the preparation of 2-chloro-2 ', 6'-diethyl-N (aeryIyloxymethyl) acetanilide. About 200 parts of 2-chloro-2 ', 6'-diethyl-N-chlorme thylacetanilide, 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 CIbH ₂₁ ) CINO ₁ :

Calculated: C 62.03, H 6.51%;

found: C 62.66, f I 6.59%.

The procedure of the preceding examples was followed using cyclopropanecarboxylic acid as reactant 2-chloro-2 ', 6'-diä (hyl-N (cyclopro

panoarboiiyloxymelhyl) aielanilid with a melting point V (in 84 to 87 ° C. Analysis for Cull ... CINO ₁ :

Calculated: C6), <) 5, H b.8 ">%; found: CbJ, -H, Il 7.00%.

Examples 19 to 1) 2

The following compounds were prepared analogously to the methods in the examples provided:

(19) 2-chloro-2 ', 6'-diithyl N- (zimlsaureaiiiidoniethyl) -ücetanilid, Melting point Mb to 147 "C.

(20) 2 chlorine 2 ', b'-diisopropyl-N (butyramidoilhyl) -aeetanilid.

(21) 2 Drom-2 ',)', 6 'irimelliyl-N (acetaniidomelhyl) aeetanilid,

Melting point I) 1 to I) 2 "C. {22) 2-iodine-2 ', b'-diethyl-4'-methyl-N (chlorine-

aeetamidoniet hy I) -acetanilide. (2)) 2 chloro-2 ', b'-di; ilhyl-N () -alhoxypropionam idomet hy I) -UCCtUn ilid, Melting point 70.5 "C.

(24) 2Chlor-2 ', 6'-diilhyl N (2-chloroacetumidomelhyl) -acetanilide, Melting point 15 to 159 ° C.

(25) 2-chloro-2 ', 6'-diethyl-N- (isobutyric acid amidomethyl) -acetanilide, Melting point I) O to 1) 3.5 C.

(2b) 2Chlor-2 ', 6'-diethyl-N (caprylamidomelhylj-acetanilide.

(27) 2-chloro-2 ', 6'-diethyl-N (/ i-chloropropionamidomethyl) acetanilide. Melting point 133 to Db'C.

(28) 2-chloro-2 ', 6'-diethyl-N (pr () pionamidomethyl) acetanilide, m.p. 144-146 "C.

(29) 2-chloro-2 ', 6'-diethyl-N (butyramidomethyl) acetanilide.

Melting point 122 to 1?), 5 ° C. (JO) 2-Ch! Or-2'.6'-diethyl-N (ureidmethyl) -acetanilide.

Melting point 206 ° C. (J!) 2-Ch! Or-2 ', 6'-diä! Hy! N (benziür.idomethy!) - acetanilide,

Melting point 1) 2 ⁼ C. (32) 2-chloro-2 ', 6'-diethyl-N- (phenylacetamidomelhyl) -acetanilide,

Melting point 135-137 ° C. (H) 2-Chtor-2 ', 6'-diethyl-N- (methacrylamidomethyl) acetanilide, melting point 106 to 108.5 ° C.

(34) 2-chloro-2'-tert-butyl-N- (valeramidomethyl) acetanilide.

(35) 2-chloro-2'-methyl-6'-ethyl-N- (acetamidomethylj-acetanilide, white solid, melting point 132 to 133 ° C.

(36) 2-chloro-2 ', 6'-diethyl-N- (2,3-dichloropropionamidomethylj-acetanilide, white solid,
Melting point 154-156 ° C.

(37) 2-Chloro-2'-methyl-6'-tert-butyl-N- (methacrylamidomethyl!) -Acetanilide. Melting point 158 to 0.5 ° C.

(38) 2-chloro-2 ', 6'-dimethyl-N- (methacrylamidomethyl) -acetanilide, white solid, melting point 159.5 to 160.5 ° C.

(39) 2-chloro-2 \ 3'-dimethyl-6'-tert.-butyl-

N - (acc ta midomc I hy I) -acc ta nil id, Melting point 16) to lb5 "C.

(40); -Hrom-2'-iT) ethyl-f) '- tert.-hiiiyl-N- (mcihacrylamidomethyl) -acetanilide, white fabric,

Melting point 151.5 to 154 "C.

(41) 2 chloro-2 ', b'diilhyl-N (cyclopropaiica rbox am idome lh y I) -acetanilide. Melting point 179 to 1 HO'C.

(42) 2-chloro-2 ', b'-diethyl-N () -methoxypropione amidomethylj-acelanilide, white solid, melting point 70.5 to 72.5 "C.

(4)) 2-Hrom-2'-ethyl-b'-lert.biilyl-N- (acelaniidomethyl) -acelanilide,
Melting point 157.5 to 159.5 "C.

(44) 2-chloro-2 ', 6'-diilhyl-N (acelainidoalhyl) acetanilide,

Melting point 8) to 8b "C.

(45) 2Chlor-2 ', 6'-diulyl-N (2 ", b" -dichlorobenzamidoethyl) -acetanilide.

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

(4 /) 2 chloro-2 ', 6'-diethyl-N (formamidoethyl) acetanilide.

(48) 2-Chloro-2 ', 6'-diethyl-N () -chloro-2-methylpropionamido-ethyl-acetanilide.

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

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

(51) 2-chloro-2 ', 6'-diethyl-N (cinnamic acid amidoethyl) acetanilide.

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

(5)) 2-chloro-2 ', 6'-dimethyl-N (siccinimidomethylj-acetanilide.

(54) 2-chloro-2 ', 6'-dimethyl-N- (succinimidoethyl) -acetanilide,

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

(55) 2-Bromo-2'-ä! Hy! -6'-methy! -N- (succinimidoethylj-ace'anilid.

(56) 2-iodo-2 ', 6'-diethyl-N- (succinimidomethyl) -acetaniüd.

(57) 2-Bromo-2 ', 6'-diethyl-N (succinimidomethyl) acetanilide.

(58) 2-chloro-2 ', 6'-diethyl-N [(2-pyrrolidinone-1-yl-ethyl-acetanilide.

(59) 2-chloro-N- (N-methylace: amidoethyl) -2 ', 6'-diethyl acetanilide.

(60) 2-Ch! Or-2 ', 6'-diethyl-N- (N-methyl-dichlorobenzamidomethyl-acetanilide.

(61) 2-chloro-2 ', 6'-diethyl-N- (N-methyl-dichlorobenzamidoethyl) -acetanilide.

(62) 2-chloro-2 ', 6'-diethyl-N- (N-ethyl-3-butenamidomethylj-acetanilide.

(63) 2-chloro-2 ', 6'-diethyl-N- (N-methyl-3-butenamidoethyl) acetanilide.

(64) 2-Bromo-2 ', 6'-dimethyl-N- (N-methylformamidomethyl) acetanilide.

(65) 2-Bromo-2 ', 6'-dimethyl-N- (methylformamidoethyl) acetanilide.

(66) 2-chloro-2 ', 6'-diethyl-N- (N-methylacrylamidornelhylj-acetaniliu.

(67) 2-chloro-2 ', 6'-diethyl-N- (N-ethyl-3-ethoxypropionamidomethyl) acetanilide.

(68) 2-chloro-2 ', 6'-diethyl-N- (N-methyl / i-chloropropionamidomethyl) -acetanilide.

(69) 2 ('lilor-2', b'-diethyl-N- (N-prc> pyl-pn) piona midomctliyl) acctanilide.

(70) 2-chloro-2'-methyl-b'-ethyl-N- (N-ailyl acctamido (ethyl) acctanilicl.

(71) 2 chloro-2 ', b'-diethyl-N- (isohutyryloxymelhyl) -acctanilide, white solid, melting point 40 to 42.5 "C.

(72) 2-Chl () r-2 ', 6'-diethyl-N- (methoxyaccloxymethyl) acetanilide.

white solid, melting point 66 to 68.5 ° C. (7J) 2-Ch! C> r-2 ', 6'-diethyl-N- (iiiethat.Tylyk> xymethyl) acctanilide, white l'estsloff, melting point 48 to 52 "C.

(74) 2-chloro-2 ', b'-diethyl-N- (cmnamyloxymctl'yl} -acctanilide, further I'cslsloff, melting point 68.5 to 72.5 ¹ C.

(75) 2 ("chloro-2 ', 6'diisopropylN- (butyryloxymelhyl) acctanilid.

(7 (i) 2-Hrom-2 ', 3', 6'-trimctliyl-N- (acct;> xy-

methyl) acctanilide (77) 2 chloro-2.6'cliethyl -N (S -iilhoxypropionyloxymctnyl) acctanilide.

brown viscous oil (7K) 2-chloro-2'.b'-cliäthyi-N- (c'aprylyloxy-

methyl) acetanilide. (74) 2 - ('chloro-2', 6 -diethyl-N - (/ i chloropropionyl-

oxyinclhy I) -IiCC ta nil id. (HO) 2 ('h! Or-2', b'-dimethyl-N- (propionyloxymctliyljacctanilide.

Melting point 64 to 65 "(Λ (81) 2 - ('lilor-2 ^r .6'-dimethyl-N- (biityryl«) xy-

methylj-acctanilide. («2) 2- (Mik) r-2'.6'-tcrt.-butyl-6'-methyl-N (accloxymethyl) acetanilide.

(83) 2 - ("hlor-2 ', 6'-diethyl-N- (carbamyloxynictliyljacetanilide.

(84) 2 ('chloro-2', 6'-diethyl-N- (phcnylaccloxymethyl) acetanilide.

(85) 2 - ('chloro-2', 6'-cliisopropyl-N- (melhacrylyc) xymethyl) -acctanilide.

(86) 2-chloro-2'-lcrt.-butyl-N- (valeryloxymethyl) -acctanilide.

(87) 2 ('chloro-2'-methyl-6'ethyl-N- (acet () xymethyl) -acclanilide.

(88) 2-chloro-2 ', 6'-diethyl-N- (1,2-dichloropropionyloxymethyl) acetanilide.

(89) 2-chloro-2'.6'-dimethyl-N- (methacrylyloxyniethyl) -acet? Nilide.

(90) 2-Chloro-2'-methyl-6'-tert-butyl-N- (methacrylyloxymethyl) acetanilide.

(91) 2-chloro-2 ', 3'-dimethyl-6'-tert-butyl-N- (acetoxymethyl) acetanilide.

(92) 2-Bromo-2'-methyl-6'-tert-butyl-N- (methacrylyloxymethyl) acetanilide.

(93) 2-iodo-2 ', 6'-diethyi-N- (cyclopropanecarbonyloxymethylj-acetanilide.

(94) 2-chloro-2 ', 6'-diethyI-N- (3-methoxypropionyloxy methyl) acetanilide.

(95) 2-chloro-2'.h'-diethyl-N- (aceioxyäthyI) -

(96) 2-chloro-2'.b'-diäthyI-N- (2 ".b ^'I -dichlorbenzoyloxyäthyl) acetanilide.

(97) 2-chloro-2'.h'-diethyl-N- (acryiyl () xyäthyl) -acetani-Md.

(98) 2-Chl () r-2'.6'-diethyl-N- (formyloxyatli> l)

acctanilid.
( ^Q 9) 2-chloro-2 ', 6'-diethylN (3 chloro -2-methyl

propinnyloxyethyl) acrlanilide. (IiX)) 2-nrom-2'.6'-diethyl-N- (acrylyl () xyalliyl) -acctanilide.

(K) I) 2-C'hl () r-2'-ethyl-6'-ine (liyl-N- (cyclopr < > paii ca rbona loxy at hy I) acctanilid.

(102) 2-ehlor-2 ', 6'-dietliyl-N- (cinnamyloxyälhyl) acctanilid.

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

(104) 2-chloro-2 ', 6'-diethyl-N- (tcrt.-btityl acctoxymcthyI) acetanilide. Melting point 64 to 69 ° C.

(105) 2-chloro-2 ', 6'-diethyl-N- (ethox> propi (insl oxy methyl) acctanilide. fluid.

(106) 2-chloro-2 ', 6'-diethyl-N- (alhoxyaceti) \> mcthyOacctanilid.
Melting point 38 to 42'C

(107) 2-niI <ir-2'.6'-diethyl-N- (hy (lr (> cinniim \ lo \\ - melhyljacclanilid,

reddish fiskosc l'lüssigkcit.

(108) 2 - ('lil () r-2', 6'-diethyl-N- (3-methylcrciion \ l oxymethylj-acetanilide.

reddish viscous oil.

(109) 2-chloro-2'.6'-diethyl-N- (accto \> MiOtIiS 1) acctanilid. white I'cMstoK. Melting point 44 to 45 C.

(110) 2-Hr (> ni-b'-tcrt.-biilyl-N- (hydm \ ynH-lli> l) o-acctoloiiiidid (2.4 (liclilorplutiox)) acetal,

Melting point KH) up to! 08 C.

(111) 2-Bromo-6'-tert-biityl-N- (li> cliox \ mclh> l) o-acctotoluidid-2.5-dichlot 3-nitrobenzoal,

Melting point 133.5 to 1 54.5 C.

(112) 2-Hrc) iii- (V-icn.-biit> 1-N- (IiV (Ii o \> met In I) -o-acctotoliiidid-3-amino
2.5-dichloibenzoate.

Melting point 126 to 129 C.

(113) 2-Rroiii-6'-tcrt.-biil \ l-N- (h \ dio \\ mclli \ i; o-acctot (i'iiidid- (2.4.5-iiichl (> i phenoxy) acetal.

Melting point 132 to 135 C.

(114) 2- »rom-6'-tcrt.-hui> IN- (hydiovymeilnI) o-acctotoluidid-2.6-CIi ( ¹ IiIoI ¹ I) Cn quotation. Melting point 133 to 139 C.

(115) 2-Bromo-b'-tert-biityI-N- (hydroxynictliNl) -o-acc (otoluidid- (2-naphthyloxy) acetal. Melting point 113 to 114 ¹ X.

(116) 2-Bromo-6'-tert-butyl-N- (hydroxymclh> l) -o-acetotoluidide piperonylate. Melting point 156.5 to 157.5 ^r C.

(117) 2-ΒΓθπν6'-1οπ. ^ Υ!> Ί · Ν- (Γ ^ Γθχ> Γηο! Π.γΙ) -o-acetotoluidide-1-naphthalene acetate. resinous liquid.

(118) 6'-tert-ButyI-2-ch! Or-N- (hydroxymethyl) -o-acetotoluidide- (2,4-dichlorophenoxy) acetate.

Melting point 93 to 94 ° C.

(119) 2-Bromo-2'-tert-butyl-6'-ethyl-N- (hydroxymethyl) -acetanilide- (2,4-dichlorophenoxy) -

Melting point 82.7 to 83.0 ⁰ C.

(120) 6'-tert-butyl-N- (hydroxymelhyl) -2-iodo-acetotoluidide- (2,4-dichlorophenoxy) -

Melting point 110.5 to 111.5 ° C

(121) 2 Bromo-6'-tert-butyl-N- (hydroxymethyl) -o aoetotoluidide salicylate. Melting point 130 to 140 ° C

(122) 2-chloro-2 ', 6'-diet: -N- (mercaptomethyl) -acetanilide-dimethyldithiocarbamate. Melting point 86 to 87 ° C

(123) 2-chloro-2 ', 6'-diethyI-N- (hydroxymethyl) acetanilide picolinate,

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

(124) 2-chloro-2 ', 6'-diethyl-N- (hydroxymethyl) -acetiinilid-nicotinate,

pitch colored solid, 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 ⁰ C.

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

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

Melting point 120 to 122 ° C.

(130) 2-3rom-6'-tert-butyI-N- (hydroxymethyl) -o-ace: totoIuidid-23,6-trichlorobenzoate, Syrup".

(131) 2-chloro-2 ', 6'-diethyI-N- (hydroxymethyl) -ao: ta nilid-piperonylat, Melting point 106 to 108 ° C.

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

In order to explain the advantages of the present invention, evaluations of the herbicidal pre-emergence properties of the haloacetanilide derivative according to the invention were determined in greenhouse studies. In each case, a specific number of seeds from a number of different plants, from each of which is a botanical. Species represented, planted in Gewächishiius bowls.

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. On the ground prepared in this way, a predetermined

te number of seeds of the different plant species The soil required for leveling the trays was applied 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

ίο sufficient moisture for germination and for Grew irrigated.

About 14 days after sowing and treating, the plants were observed and the results held. The herbicidal rating was by means of a fixed scale based on the average percentage germination of each seed lot 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 «-halogen-

acetanilide is in the table below with the different application conditions both at

Surface applications as well as when being introduced into

indicated the soil.

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 A, 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

1 = hemp sesbania

J = white goosefoot K = Cissampelos pareira L = Bromus Tectorum M = Panicum spp. N = chicken millet O = finger millet

(Digitaria sanguinalis)

Table I.

Ver To whom- Plant species B. C. I) I- I. 0 Il I. J K 3 M. N O am durgs- 0 3 manure vcrlialt- Λ 1 3 from nis I. 0 2 3 0 I. 0 (I. 1 3 3 3 example (kg / ha) ·) 0 2 ~)
Δ 3 (I. (I. (I. (I. I. 3 3 3 I. V 0 I. 2 0 2 (I. 0 2 (I. (I. 2 3 3 IVM I. B09 617/223 4th IV 0

continuation

Ver To whom- Plant species 1 B. C. D. E. F. G H I. 1 J 2 K L. M. N O am manic 0 0 0 manure relative- A. 0 2 1 from nis 0 0 3 3 3 0 1 0 0 0 1 3 3 3 3 example (kg / ha) *) 0 0 0 0 0 1 0 0 0 0 0 0 2 3 1 5 IVM 1 2 0 2 3 1 0 0 0 2 0 2 3 3 2 6th IV 0 0 0 0 3 0 1 1 1 0 0 2 ' 3 3 3 7th IV 0 0 0 0 0 2 0 1 2 0 0 0 2 3 C. 8th II 0 - 1 1 0 0 0 0 2 3 0 I. 1 3 3 I. 0 1 0 0 0 0 0 0 1 0 0 ü 1 2 2 10 : iv 0 0 0 0 2 0 0 0 2 1 0 2 2 3 3 II 0 1 0 1 0 0 0 0 1 0 0 0 1 3 3 11th ZV 0 0 1 3 2 0 0 0 0 0 0 2 3 3 3 ul 0 0 1 0 0 0 0 0 0 1 0 0 3 3 3 [VM 1 0 0 0 0 0 0 0 1 3 0 0 3 3 2 12th II 0 0 0 0 1 0 0 1 2 3 0 2 2 3 3 I. 0 1 0 0 2 3 2 0 2 2 0 1 1 3 1 14th IV 0 1 0 1 1 0 2 0 3 2 1 1 2 3 3 15th IV 0 0 0 0 0 0 2 0 1 2 0 0 1 2 2 16 IV 0 2 2 1 2 0 1 1 1 0 0 2 2 3 3 17th IV 0 2 2 3 2 0 0 0 1 0 0 3 3 3 3 18th IV 0 0 2 3 2 0 0 0 2 3 0 3 3 3 3 23 IV 1 0 0 1 1 0 0 0 1 2 0 1 2 3 2 AROUND 0 0 0 3 3 0 0 0 1 0 0 3 3 3 3 25th IV 0 3 3 3 3 0 0 1 2 3 0 3 3 3 3 27 IV 0 1 3 2 3 0 1 0 1 2 0 3 3 3 3 28 IV 0 1 0 0 0 0 0 0 0 1 0 0 0 3 3 29 IV 0 2 1 3 3 0 1 0 1 0 0 3 3 3 3 30th IVM I. 1 0 2 2 0 0 0 0 0 0 2 3 3 3 35 IV I. 2 0 1 1 0 2 0 1 0 0 2 2 3 3 36 IV 1 0 1 1 0 0 0 0 0 0 0 3 3 3 3 37 IV 1 0 0 0 1 0 0 1 1 0 1 0 2 3 3 Il 0 1 1 I. 3 0 0 2 1 0 1 3 2 3 3 38 IVM 0 0 0 0 1 0 0 1 1 0 0 0 1 3 2 39 IVM 0 1 1 1 3 0 0 2 2 1 0 1 3 3 3 40 IVM 0 0 0 2 1 0 1 1 0 1 0 2 3 3 3 41 IVM ^v 0 0 1 1 3 0 1 0 0 0 0 3 3 3 3 42 IVM 1 0 0 0 3 0 0 0 1 3 0 1 3 3 3 43 IVM 0 0 0 1 0 0 0 0 1 2 0 1 1 3 3 I! 0 0 0 0 1 0 0 0 0 1 0 0 1 3 3 44 IVM 0 1 0 0 1 0 2 0 0 1 2 2 2 3 2 i: 2 3 0 1 0 0 2 0 3 3 0 0 2 3 2 73 IV 0 0 0 0 I. 0 2 0 0 1 1 2 2 3 3 74 IV 0 0 0 0 0 0 0 0 0 1 0 3 2 3 2 75 0 2 0 0 2 0 1 I. 2 I. 0 2 I. 2 2 76 1 1 0 0 0 1 0 0 1 0 0 3 3 I. 107 1 0 0 0 0 0 0 0 0 3 3 1 108 2 I. 1 1 0 1 0 0 2 2 3 3 109 0 2 3 2 0 0 0 0 3 3 3 3 111 112 V V 7th V 7th 7th V

continuation

Ver To whom- Plant species = 0 ^ 62 D. E. F. - G H am manic = 0.281 - manure behaved- ABC = 1.125 from nis = 5.625 _ 3 2 2 Example 1 (kg / ha) ·) - 3 1 1 122 V 2 2- rv 1 2 *) Application ratio (kg / ha) I. U Iv V

The figures from the previous table clearly show that the compounds of the present invention are effective herbicides and 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 as follows 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 II

(35 parts of the butylamine salt of dodecylbenzenesulfonic acid and 65 parts of tall oil, condensed with ethylene oxide in Ratio of 11 moles of ethylene oxide to 1 mole of tall oil) contains, is used in the plants in different sets of trays with different application ratios of the active ingredient The treated Plants are placed in a greenhouse and the effects observed and after approximately 14 days held.

The index of the herbicidal post-emergence efficacy is defined as follows:

Reaction of the plant

index

No damage. Slight damage. Moderate damage. Severe damage Killed

3 »

are denoted by the following letters:

1 =

The plant species used in these experiments 4 "H = maize Foxtail grass Chicken millet Finger millet

Amaranth

Soybean'

Wilder book ways

tomatoes

Sorghum

A = funnel winch B - flying oats C - bluegrass

D - ryegrass

E - radish

F - sugar beet G - cotton

K L

45 M N O P Q

Table HI Herbicide post-emergence effectiveness

Connection application

Example ratio

(kg / ha) ·)

Plant species ABCDEF

GHI MNO

IH

III IV IV

*) Application ratio (kg / ha) III = 0.450 IV- 1.125

4 10 0 4 4

4 2 1 14 4

3 0 0 0 4 4

4 10 14 4

4 2 2

4 2 2

4 0-

4 1 I.

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 known as "propachlor" will. When i * ian those in the present description using the rating scale given in Table I for the relative herbicidal activity, one can recognize that the tested compounds of the invention do not cause damage to valuable cereals, soybeans and rice while they are at the same time keep the weeds under control, d. H. moderate to severe damage to the offending Bromgrass weeds that grow up with the crops. In contrast, that holds 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 bromgrass to grow so that it flourishes collectively, not prevent it.

25th

Table IV relationship ; soy rice Bromine 30 beans grass (kg / ha) Herbicide pre-emergence effectiveness 1.12 0 0 3 link 0.28 0 0 2 35 from example 1.12 0 0 2 No. 1.12 0 0 2 4th 1.12 0 2 0 8th 0.28 0 1 0
4C 14th *) Active ingredient (N-isopropyl ^ -chloroacetanilide) in 70 “Ramrodw herbicide. Propachlor *)

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) ,. The preparations are produced by the fact that the active ingredient with a so Auxiliaries, such as a diluent, extender, carrier and conditioning agent, mixes to make preparations in the form of finely divided particulate To create solids, granules, pellets, solutions, dispersions or emulsions. It can therefore be the Active ingredient together with an auxiliary, such as a finely divided solid, an organic liquid 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 one or more surface-active agents as conditioning agents in such amounts that one given preparation lightly in water or in oil (, 5 is dispersible. Including a surfactant in the preparations increases their Effectiveness essential. The term "surfactants" includes, inter alia. Wetting agents, dispersants, suspending agents or emulsifying agents. Anionic, cationic and nonionic agents can can also be used with good success.

The preferred wetting agents are alkylbenzene and alkylnaphthalene sulfonates, sulfated fatty alcohols, amines or acid amides, long-chain acid esters of Sodium isoethionate, esters of sodium sulphon succinate, sulfated or sulfonated fatty acid esters, petiolsulfonates, sulfonated vegetable oils, ditertiary acetylenic glycols, polyoxyethylene derivatives of alkylphenols (especially isooctyiphenol and nonylphenol) or Polyoxyethylene derivatives of the mono-higher fatty acid esters of hexitol anhydrides (for example sorbites). Preferred dispersants are methyl cellulose, polyvinyl alcohol, sodium lignin sulfonates, polymeric alkyl naphthalene sulfonates, sodium naphthalene sulfonate and / or polymethylene bisnaphthalenesulfonaL

Wettable powders are water-. : 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 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 approximately 94.5 parts of inert solid extender, all parts by weight of the total formulation are related. If desired, about 0.1 to 2.0 parts solid inert diluent can be added through a Corrosion inhibitor or an anti-foaming agent or both can be replaced.

Aqueous suspensions can be prepared by having an aqueous slurry of Vice-insoluble active ingredient is mixed together in the presence of dispersants and grinds to form a to obtain concentrated slurries of very finely divided particles. The concentrated aqueous Suspension has an extremely small 1 particle size, so that with dilution and spraying the coverage is very uniform

Emulsifiable oils are usually solutions of the Active substance in water-immiscible or partially water-miscible solvents, together with a surfactant. Appropriate solvents for the active ingredients of these Invention include hydrocarbons and water-immiscible ethers, esters or ketones. the emulglefbirefl Offifereitningen generally contain from about 5 to 95 parts of active ingredient, about 1 to 50 parts surfactant and approximately 4 to 94 parts solvent, all parts by weight and based on the total weight of the emulsifiable oil.

Granules are physically stable, tick-shaped, Preparations containing the active ingredient, the active ingredient being based on a matrix an inert, finely divided particulate extender adheres or is given to the leaching of the To support the active ingredient from the particulate matrix, a surfactant such as it previously specified must be present in the preparation. Natural clays, pyrophvllite, illite and

Vermiculite are examples of useful substances gcr mineral extenders. The preferred stretch Means are porous, absorptive, preformed 'particles, like preformed and sieved, divides egg-shaped altapulgite or wiirnieexpanded. particulate Vermiculil and the finely divided ions, such as Kaolmloiic, hydrated allapiilgil or llenlonittone. /.ur HiI dung herbicider (iranulate these extenders sprayed on or mixed with the active ingredient

The (iraiulatzubitungen of this invention contain about ^r > to about JO (iew. Parts active ingredient per 100 (iew parts clay and 0 to about ¹ J (iew. File surfactant per KK) (iew. Parts particulate ion) The preferred granular fractions contain about 10 to about 2 ^r > (iew. ■ part · active ingredient pt ο 100 (iew. -'feile lon.

The preparations of this invention can also other additives such as fertilizers. Herbicide and other Scliädlmgsvertilgungsmillcl contain, as an aid or together with mil any of the auxiliaries described above can be used. To connections that go to the Combination with ilen active ingredients of this invention are suitable include, for example, triazines, urine fabrics. Carbamates. Acetamides, Acetanilides, Uracils, Acetic Acids. Phenols. Thiocarbamates, triazoles. Ben zoic acids and nitriles. Other useful aggregates include materials in which plants Put down roots and grow like compost, manure, humus and sand.

When operating in accordance with the present invention, effective amounts of the present invention I lalogenacetanilide 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 fuel systems in plants or on the ground using conventional methods, for example power atomizing, tree and I landspi'uhgerä'lcn and Spriihzerstaiibeni, I) u Because of their effectiveness, preparations can also be taken from airplanes in low doses. Dust or spray are applied. Dit. Use of the herbicidal preparations with water planting is usually done in the manner that the preparations ar admits the position. \ w> one wishes to control the aquatic plants.

The invention of an effective amount of the compound fertilize these inventions on the plant is essential and decisive for the herbicidal effect of the preparations according to the invention. Exactly The amount of active ingredient to be used depends on various factors such as the plant species the stage of development, the soil and soil conditions, the amount of rain and the specific I lalogenacctanilid used according to the invention Derivative. With non-selective pre-emergence treatment, the compounds of this invention become habitual applied in proportions of 1 to 30 kg / ha. Z.iii selective pre-emergence use for plants or soils, dosages of 0.002 bis <are usually used 5,650 kg / ha used. In some cases, lower or higher application ratios may be required be so. From this description, including dei Examples, however, by simple experiments the man can easily find the answer for any particular case determine which optimal ratio to use.

The term "soil" is used here in its broadest sense and includes everyone Convenient soils such as those in Webster's New International Dictionary, Second Edition. Unabridgei (1961). are defined. It therefore refers to diesi Term for any substance or medium in which plants can take root and grow and not only the clearing as such, it also secretes compost. Fertilizer. Manure, humus and sand which are suitable for supporting plant growth.

Claims (1)

Claims: ■ 1. Malogenaceianilide derivatives of the general formula (ΉΛ (CH_, I "Λ R ¹