CA1213288A

CA1213288A - Anilides and herbicides containing them

Info

Publication number: CA1213288A
Application number: CA000403891A
Authority: CA
Inventors: Rainer Becker; Ulrich Schirmer; Bruno Wuerzer
Original assignee: BASF SE
Current assignee: BASF SE
Priority date: 1981-06-15
Filing date: 1982-05-27
Publication date: 1986-10-28
Also published as: HU190801B; EP0067381B1; ATE6775T1; ZA824150B; DE3123733A1; BR8203449A; EP0067381A1; DE3260075D1; JPS57212147A

Abstract

Abstract of the Disclosure: Anilides of the general formula where X is hydrogen, fluorine, bromine, iodine, alkyl, alkoxy, haloalkyl, haloalkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, phenyl, benzyl or benzyloxy and Y
is hydrogen, halogen, alkyl, alkoxy, haloalkyl, halo-alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, phenyl, benzyl or benzyloxy, or X and Y together are a 3-membered or 4-membered alkylene or alkenylene radical, n is 1 or 2, Z is hydrogen or halogen and R is alkyl of 1 to 4 carbon atoms or alkoxyalkyl of 2 to 5 carbon atoms, and Z is trifluoromethyl if X is haloalkoxy, are used in herbicides.

Description

~LZ~3~
l - OOZE. 0050/3~205 Anilides and herbicides containing them to present invention relates to anilides, herbicides containing these compounds as active ingredi-ens, and a method of controlling undesirable plant growth using these compounds.
British Patent guy has disclosed the use ox 3,4-dichloropropionic acid aniline as a herbicide, in particular as a herbicide for rice. However its toleration by soybean and Indian corn is inadequate.
A pertain improvement in the selectivity of herbicidal anilides in these crops has been achieved with Cyril-anilides 7 ego Of S COOK (British Patent 1,344,735) Of and with 0-aryla~ilidesg ego Al 0 NHCCC2~5 (US. Patent 3,976,470).
Of We have found that anilides of the general for mute I

X 0 issuer (I) Yin Z
where X is hydrogen, fluorine bromide, iodine, alkyd, alkoxy, haloalkyl, haloalkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl of l to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, phenol, bouncily or benzyloxy and y ~~',

2~3~
- 2 - ooze. 0050/35205 is hydrogen, halogen, alkyd, alkoxy, halsalXyl, halo-alkoxy, alkylthio, alkylsulfiny~l or alkylsulfonyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, phenol, bouncily or benzyloxy, or X and Y together are a saturated or unsaturated 3-membered or 4-membered alkaline radical, n is 1 or 2, Z is halogen and R is alkyd ox 1 to 4 carbon atoms or alkoxyalkyl of 2 to 5 carbon atoms, and is trifluoromethyl if X is haloalkoxy, are very useful for controlling undesirable plants in crops such as rice, cereals, groundnuts and the like. m e unexpectedly good toleration of specific compounds by soybean and Indian corn, whilst extremely important bridled weed species are destroyed, is surprising X and Y are, for example hydrogen, phenol, benzyloxy~, fluorine, bromide, iodine, straight-chain or branched alkali alkoxy~ haloalkyl, haloalkoxy, alkylthio, alkylsul~inyl or alkylsulfon~l of 1 to 6 carbon atoms, preferably of 1 to 4 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, ego methyl, eighth, isopropyl, n-propyl, isobutyl, tert.-butyl, n-pentyl, n-hexyl, methoxy, elk-isopropox~s~, sec.~-butoxy~, trifluoromethyl, Delaware-methoxy, trifluoromethoxy, 2-chloro-2,1,1-trifluoro-methoxy, methylthio, me-thylsulfonyl, isopropylthio and cy~lohexyl, and Y can also be chlorine. If n is 1, X
and Y together can also be a 3-membered or 4-membered alkaline or alkenylene radical which is unsubstituted or `:
substituted by methyl, ego a trim ethylene, tetramethylene 1,1,3,,3-tetr~methyltrimethy~lene or buta-1,3-dienylene.
radical, .

.
.
`

`` I

- 3 - OOZE. 0050/35205 I, Z is, for example fluorine , chlorine or Bryan.
Z can also be trifluoromethyl if X is haloalkoxy .
R is, for example, alkyd of 1 to 4 C atoms and alkoxyalkyl of 2 to 5 C atoms, ego methyl, ethyl, I: npropyl, i-propyll n bottle, methoxymethyl or l-me~hoxy-ethyl I . . Preferred compounds of the formula I are those ' where X is alkyd, alko~y-or haloalkoxy, each of 1 to 4 J carbon atoms .10 The anilides of the formula I are obtained, for example, by reacting an amine of the formula II.

X~0~2 1. . Yin Z (II) 3 where X, Y, Z and n have the above meanings, with an acid chloride of the formula III
Clocker (III) or an acid android of the formula R-CO-O-CO-R9 where R has the above meanings, in the presence ox an acid acceptor and a solvent ` Examples ox suitable solvents are water, Alcoa hots, in particular aliphatic alcohols ego methanol, ethanol and isopropanol, aliphatic chlorohydrocarbons9 I ego chloroform, ethylene chloride and dichloroethane~
and kittens, ego acetone, deathly eighteen and methyl.
ethyl kitten.: .
Suitable cold acceptors include the conventional . ..

.

- 4 - OOZE. 0050/35205 I bases such as alkali metal hydroxides, bicarbonates and s carbonates, alkaline earth metal oxides, hydroxides, bicarbonates and carbonates and tertiary organic bases, especially sodium hydroxide sodium carbonate sodium f bicarbonate, calcium oxide, triethylamine9 pardon, N,N~dimeth~laniline~ N9N-dimethyl cyclohexyl~mine, f quinoline and tri-n-butylamine.
e starting substances ox the formulae II and including the acid hydrides are used in approxi-10 Mattel stoichiometric amounts, Leo not more than 10 mole % more or less of starting substance of the formula II is used in comparison with starting substance of the formula III. The reaction is carried out at prom ---20 to ~150C, preferably from +20 to *60C.
Some of the amine of the formula II are known they can be prepared by the methods described in ; Hobnail, Methadone don organ. Chemise, volume XI/l, page 341 et seq., George Thieme-Verlag, Stuttgart, 1957.
The acid chlorides ox the formula III and the acid 20 androids are known.

2~.8 parts by weight ox 4 (4'-ethylphenoxy)-3-chloroaniline were dissolved in 200 parts by weight of acetone, and 12.6 parts by weight of sodium bicarbonate dissolved in 150 parts by weight of water were added.
` 11.6 parts by weight ox propionyl chloride were then added drops at 20C. The mixture was subsequently stirred at room temperature for some hours, poured into ice-water and filtered with suction. 28.9 parts by , I

_ 5 _ OOZE. 0050/35205 ; weight of N-4-(4'-ethylphenoxy) 3-chlorophenyl-' propionamide of melting point 83 - 85C were obtained.
The-following compounds, for example, were pro pared Al cor=e~cn~ ruckuses.

.

.

6 - 0 .. Z . 0050/35205 i ,' X~O~NH-C0-R
i. Y
n No X Y Z R rip n it 1 2 5 H Of ~2H5 83 - 85 C
, 2 6 5 H Of C2H5 131 - 133 C
3 OOZE H Of OH 100 102 C
4 OCHF2 En H C2H5.108 - 110 C

5 OCHF2 H Of C2~5 71 - 73 C

6 OOZE H Of clue 97 - 100C
Of C2~5 97~ SKYE
H 'rip Of C2H51 lo - 112 C
5 n-C3H7 H Of C2H5 67 - 69C
I 10 icky H Of C2H5 92 - 93 C
I t-C4Hg H Of. C2H5 118 - 121 C
n~4H9 H Of C2H5 78 80C
13 Clue H Of C2H5 130 - 132 C
14 icky H Of C2H5 I l lSOC3H7 (n) H Of C2H5 72 - 75 C
17OCF Shekel H Of C2H5 79 81C
13OCF2CHFCl H H C2 5 123 - 125-C

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- 7 - Ooze. 0050/35205 Nub X Y Z R
lo 19 OUCH H Of CH20CH3 68 70C
SHEA H Of C2~5 98 or 100 C

1 22 (C~2)3 Of c22H~ 93 95 C
j 23 -(GO YO-YO in Of C2H5 113 - 114 C
24 (OH) 4J 5-positioncl Cc22H5 113 - 115 C

27 H OKAY Go C2H5 oil 28 H clue Of C2H5 101 _ 103 C
29 SCHICK H Cal Cc22H55 83 - 85 C

31 -C(C~ )2C~2C(C~3)2 C2H5 107 - 110 C
Ye in 3-position C2H5 80 - 83 C

33 C2H5 H Of CH(CH3)0C~ 51 - 53 C
34 OCHF2 H Of PSYCHIC oil OCHF2 H H CH(CH3)0C~3 98 - 100 C
C2~5 Of SWISH 108 - 110C
41 OH Of n-C4Hg oil Ll5 OUCH H Of CH(CH,)CCH3 oil C6H_ H H OH 202 - 204 C
I OUCH_ H Of CH(C~3)0CH3 a- link I SHOWOFF H CF3 SHEA oil The following compounds may be prepared analogously:

of

8 - OOZE 0050/35205 I .

No, X n R

i, 26 By H Of C2H5 36 CF3 H Of C2H5 38 C2H5 H . Clunk ' 39 CH(CH3)2 H Con C3H7 Jo 42 C2H5 H By C2H5 43 n-C3H7 H Of ( 3) 3 44 SCHICK H C1 ( 3 3 ,, 10 47 OUCH H Of 3 7 The influence of representatives of the novel herbicidal anilides on the growth of unwanted and crop plants is demonstrated in greenhouse experiments.

1, 1' 1, I

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. - 9 ooze. 0050/35205 List of plants used in the experiments Botanical name Abbreviation in table _ _ _ _ .
Amaranths sup.
Amaranths retro~lexus Arachys hypogaea Arachys hype Couch lore Chenopodium album Chenopod. alp.
, Euphoria nucleate EuphorbO genie.
'I Gallium apron Gleason Max Hordeum vulgar Lamium purpureum Lamium purr.
Lamium sup.
Ours saliva Ours satin.
Sesbania exaltata Sesbania exalt.
Side puns Ida spin Synapse alga ~riticum aestivum Critic. cost.
Zeta may The vessels employed were plastic flowerpots having a volume of 300 cm , and which were filled with a sandy loam containing about lo humus. The seed of the test plants were sown shallow, and separately, according to species. In the case of soybean, i peat was added to ensure better growth. The rice plants were also grown in a peat enriched substrate An impairment of the results on leaf treatment post emergence treatment) is not to be feared, particularly as the prior art comparative compounds are used under lo ooze. 0050/35205 the same conditions. For this pos~emergence treatment, plants were used which had been sown direct in the experiment vessels and had grown there, or which had been grown separately as seedlings and transplanted into the experiment vessels a few days before treat-mint. The test plants were then from 3 to 15 cm Howe depending on growth form The active ingredients were applied by suspending or - emulsifying spray powders or emulsion conceIltrates of the active ingredient in water, and spraying the mixture through finely distributing nozzles. The prior art agents used for comparison purposes were A Of 0 NHCOC2H5 C1 So 3,976,470) B Of S NHCOC2H5 (British 344, 735) I
and C Of NHCOC2H5 (British 903,766)~

Of In the post emergence treatment, the application rates varied from active ingredient to active ingredient, and were either 0.25, 0.5 or 1.0 kg/ha.

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3~81 I;, '' O . Z . 0050/35205 ;¦ In the reemergence treatment, the active ingredients were Jo applied (here too in water as vehicle) immediately after the test plants had been planter. Shortly before or after plotting the soil was sprinkler irrigated to initiate swelling and germination of the seeds Transparent plastic covers were then placed on the vessels to ensure uniform germination, insofar as this was not impaired by the chemicals.
The pots were set up in the greenhouse - species from warmer areas at from 20 to SUE and species from moderate climates at 10 to 25C. The experiments were run or from 2 to 4 weeks.
I, During this period, the plant were tended and their reactions to the various treatments assessed. The scale used for assessment was 0 to 100, 0 denoting no damage or normal emergence, and 100 ' denoting non emergence or complete destruction of at least the J. visible plant parts.
Jo on investigations in the greenhouse into selective herbicidal action on post emergence application, compound no 27, at Al 0.5 kg/ha, was tolerated by soybeans much better than prior art I: comparative agent An and also combated important broad leaved I weeds.
Jo The greenhouse experiments also revealed that compound I no. I on post emergence application at 1.0 kg/ha~ had an Jo excellent herh~cidal action and damaged neither soybean nor Indian corn plants. Comparative compound C caused considerable damage Prior art comparative compounds A and B, which are chemically closer, also caused heavy damage to these crops, although not as much as agent C.
The greenhouse experiments further showed that the novel Jo an.ilides, such as compounds nos. 5 and 1 at 0.5 kg~ha applied I`:

- 12 - ooze. 0050/35205 post emergence, had a very good action on various broad leaved weed species, without damaging groundnut plants.
In post emergence application tests in the greenhouse active ingredients nosy 2, 3, Al 10, 13, 14, 17, 21, 23, 28, 29 and 30, at 1~0 kg/ha, had a more or less strong action on broad leaved unwanted plants and were well tolerated by rice and wheat plants.
These greenhouse experiments further revealed that compound no. 9, applied post emergence at 0.25 kg/ha, and compound no. 16 7 applied post emergence at 0~5 kg/ha, had a good action on broad-leaved unwanted plants and were selective in crop plants such as rice, wheat, groundnuts and soybeans. Compound no. 28, appliedpostemergence at 0.5 kg/ha, exhibited a good herbicidal action on broad leaved weeds without damaging the cereal specie barley Compound nos. 14, 11 and 17 r applied reemergence at 3.0 kg/ha, had a herbicidal action on Synapse alga as broad leaved test plant.
The agents may be applied during emergence of the unwanted plants, but are preferably applied post emergence (leaf treatment.
If certain crop plants tolerate the active ingredients less well, I application techniques may be used in which the herbicidal agents are sprayed from suitable equipment in such a manner that the leaves of sensitize crop plants are if possible not touched, and the agents reach the soil or the unwanted plants growing beneath the crop plants (post-directed, lay-by treatment The amount of active ingredient applied depends on the growth stage of the plant and the Sicily of the year, and varies from 0.1 to 10 kg and moxie of active ingredient per Hector.
To increase the spectrum of action and to achieve synergistic effect, the novel anilides may be mixed and applied together with ~2~8~3 - 13 OOZE. OOZE
numerous representatives of other herbicidal or growth-regulating active ingredient groups. Examples of suitable mixture components are Dennis, 4H-3,1benzoxazine derivatives, benæothiadiazinones, such as 3-isopropyl-2,1,3-benzothiadiazin-4-one-2 t 2-dioxide and its sodium salt, 2,6-dinitroanilines, N-phenylcarb~mates, trio].-garb mates, halocarboxylic acids treasons, asides, ureas, diphenyl ethers, triazinones, uracils, benzofuran derivatives, cyclohexane-1,3--dione derivatives, etc.
It may also be useful to apply the novel compounds, either on their own or combined with other herbicides, in admixture with other crop protection agents, ego agents for combating pests or phytopathogenic fungi or bacteria The compounds may also be mixed with solutions of mineral salts used to remedy nutritional ox trace element deficiencies Non-phytotcxic oils and oil concern-trades may also be added Application may be effected for instance in the form of directly spray able solutions, powders suspensions, dispersions, emulsions, oil dispersions, pastes, dusts broadcasting agents, or granules by spraying, atomizing, dusting, broadcasting or watering. the ohms of application depend entirely on the purpose for which the agents are being used, but they must ensure as fine a distribution ox the active ingredients as possible For the preparation of solutions, emulsions, pastes and oil dispersions to be sprayed direct, mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil 9 further ; coal-tar oils and oils of vegetable or animal origin, aliphatic~
I` cyclic and aromatic hydrocarbons such as Bunsen Tulane zillion, paraffin, tetrahydronaphthalene, alkylated naphthalenes and their derivatives such as methanol, ethanol propanol, buttonhole, sheller :`

I

form, carbon tetrachloxide, cyclohexanol~ cyclohexanone, sheller-Bunsen, isophorone, etc., and strongly polar solvents such as dimethylformamide, dim ethyl sulfoxide, N-methylpyrrolidone, water, etc. are suitable Aqueous formulations may be prepared from emulsion concern-trades, pastes, oils dispersions or wettable powders by adding water. To prepare emulsions pastes and oil dispersions the in-gradients as such or dissolved in an oil or solvent may by home-jounced in water by means of wetting or dispersing agents, ad-hornets or emulsifiers. Concentrates which are suitable for dilution with water may be prepared from active ingredient, wetting agent, adherent, emulsifying or dispersing agent and possibly solvent or oil.
Examples of surfactants are: alkali metal, alkaline earth metal and ammonium salts of ligninsulfonic acid, naphthalenesul ionic acids, phenolsulfonic acids, alkylaryl sulfonates, alkyd sulfates and alkyd sealants, alkali metal and alkaline earth metal salts of dibutylnaphthalenesulfonic acid, laurel ether sulfate, fatty alcohol sulfites, alkali metal and alkaline earth metal sells ox fatty acids, salts ox sulfated hexadecanols, Hyatt-decanol~, and octadecanols, sells of sulfated fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ethers, ethoxylated isooctylphenol, ethoxylated octylphenol and ethoxylated nonyl phenol, alkylphenol polyglycol ethers, tributylphenyl polyglycol ethers, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyp I
..

(I

~2~3~88 - 15 - OOZE. 0050/35205 oxyethylene alkyd ethers ethoxylated polyoxypropylene~ laurel alcohol polyglycol ether acutely, sorbitol ester, Logan, sulfite waste liquors and methyl cellulose.
Powders, dusts end broadcasting agents may be prepared by mixing or grinding the active ingredients with a solid carrier.
Granules ego coated, impregnated or homogeneous granules, may be prepared by bonding the active ingredients to solid carriers. Examples of solid carriers are mineral earths such as silicic acid, silica gels, silicates, talc, kaolin, Attaclay, lo limestone, lime, chalk, bole, loss, clay, dolomite diatomaceous earth, calcium sulfate magnesium sulfate magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate and ureas, and vegetable products such as grain flours bark meal wood meal, and nutshell meal, cellulosic powders, etch The formulations contain from 0.1 to 90, and preferably 1 to 60, by weight of active ingredient.
Examples of such formulations are given below.
EXAMPLE
90 parts by weight ox compound l is mixed with lo parts by weigh of N-methyl-alpha-pyrrolidone. A mixture is obtained which is suitable for application in the Norm of very fine drops.
E.YA~IPLE II
lo parts by weight of compound 27 is dissolved in a mixture consisting of 90 parts by weight of zillion 6 parts by weight of the adduce of 8 to lo moles of ethylene oxide and l mole of oleic acid-N-monoethanolamide, 2 parts by weight of the calcium salt of dodecylbenzenesulfonic acid and 2 parts by weight of the adduce of 40 moles of ethylene oxide and l mole of castor oil.

I
ooze. ooze EXAMPLE III
20 parts by weight of compound 20 is dissolved in a mixture consisting of 60 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, S parts by weight of the adduce of 7 moles of ethylene oxide and 1 mole of isooctylphenol, and 5 parts by weight of the adduce of 40 moles of ethylene oxide and 1 mole of castor oil EAGLE IV
20 parts by weight of compound 1 is dissolved in a mixture consisting of 25 parts by weight of cyclohexanone, 65 parts by weight of a mineral oil fraction having a boiling point between 210C and 280C, and 10 parts by weight of the adduce of 40 moles of ethylene oxide and 1 mole of castor oil.
EXAMPLE
80 parts by weight of compound 5 is well mixed with 3 parts by weight of the sodium salt of diisobutylnaphthalene-alpha-~ulfonic acid, 10 parts by weight of the sodium salt of a Logan--sulfonic acid obtained from a sulfite waste liquor, and 7 parts by weight of powdered silica golf and triturated in a hammer mill.
EXAMPLE VI
5 parts by weight of compound 2 is intimately mixed with 95 parts by weight of particulate kaolin. A dust is obtained containing I by weight of the active ingredient.
EXAMPLE VII
30 parts by weight of compound 3 it intimately mixed with a mixture consisting of 92 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil which has been sprayed onto the surface of this silica gel. A formulation of the active ingredient is obtained having good adherence.

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EXAMPLE VIII
40 parts by weigh of compound 6 is intimately mixed with 10 parts of the sodium salt of a phenolsulfonic acid urea-form-alluded condensate; 2 parts of silica gel and 48 parts of water to give a stable aqueous dispersion.
EXAMPLE IX
20 parts of compound 1 is intimately mixed with 12 parts or the calcium salt of dodecylbenzenesulfonir acid, 8 parts of a fatty alcohol polyglycol ether, 2 parts ox the sodium salt ox a I phenolsulfonic acid-urea-formaldehyde condensate and 68 parts of a paraffinic mineral oil. A stable oily dispersion is obtained.

I

Claims

The embodiments of the invention in which an exclusive property or privilege is claimed are defined as follows :

1. An anilide of formula (I) (I) where X is hydrogen , fluorine , bromine , iodine , alkyl, alkoxy , haloalkyl , haloalkoxy, alkylthio , alkylsulfinyl or alkylsulfonyl of 1 to 6 carbon atoms , cycloalkyl of 3 to 6 carbon atoms , phenyl , benzyl or benzyloxy and Y is hydro-gen , halogen , alkyl, alkoxy, haloalkyl , haloalkoxy , alkylthio, alkylsulfinyl or alkylsulfonyl of 1 to 6 carbon atoms , cycloalkyl of 3 to 6 carbon atoms , phenyl, benzyl or benzyloxy , or X
and Y together are a 3-membered or 4-membered alkylene or alkenylene radical , n is 1 or 2, Z is halogen and R is alkyl of 1 to 4 carbon atoms or alkoxyalkyl of 2 to 5 carbon atoms , and Z is trifluoromethyl if X is haloalkoxy .

2. An anilide of the formula (I) as claimed in claim 1 , selected from the group consisting of N-4-(4-ethyl-phenoxy) -3-chlorophenylpropionamide , N-4-(4-difluoromethoxy-phenoxy) -3-chloro-phenylpropionamide , N-4-(4-methylthiophenoxy)-3 - chlorophenylpropionamide , and N-4-(3-methoxyphenoxy)-3-chlorophenylpropionamide .

3. A process for combating unwanted plant growth , wherein the soil or the plants are treated with a herbicidally effective amount of an anilide of the formula (I) (I) where X is hydrogen , fluorine , bromine , iodine, alkyl, alkoxy, haloalkyl , haloalkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl of 1 to 6 carbon atoms , cycloalkyl of 3 to 6 carbon atoms , phenyl, benzyl or benzyloxy and Y is hydrogen , halogen, alkyl, alkoxy, haloalkyl , haloalkoxy , alkylthio , alkylsulfinyl or alkylsulfonyl of 1 to 6 carbon atoms , cycloalkyl of 3 to 6 carbon atoms , phenyl, benzyl or benzyloxy , or X and Y
together are a 3-membered or 4-membered alkylene or alkenylene radical , n is 1 or 2 , Z is halogen and R is alkyl of 1 to 4 carbon atoms or alkoxyalkyl of 2 to 5 carbon atoms , and Z
is trifluoromethyl if X is haloalkoxy .

4. A process for combating unwanted plant growth as claimed in claim 3 , wherein the anilide of formula (I) is selected from the group consisting of N-4-(4-ethylphenoxy)-3-chlorophenylpropionamide , N-4-(4-difluoro-methoxyphenoxy)-3-chlorophenylpropionamide , N-4-(4-methyl-thiophenoxy)-3-chlorophenylpropionamide , and N-4-(3-methoxy-phenoxy)-3-chlorophenylpropionamide .

5. A process for producing an anilide of the formula (I) (I) where X is hydrogen , fluorine, bromine, iodine , alkyl, alkoxy, haloalkyl, haloalkoxy , alkylthio, alkylsulfinyl or alkylsulfonyl of 1 to 6 carbon atoms , cycloalkyl of 3 to 6 carbon aroms , phenyl, benzyl or benzyloxy and Y is hydrogen , halogen, alkyl, alkoxy , haloalkyl, haloalkoxy , alkylthio , alkylsulfinyl or alkylsulfonyl of 1 to 6 carbon atoms , cycloalkyl of 3 to

6 carbon atoms , phenyl, benzyl or benzyloxy , or X and Y toge-ther are a 3-membered or 4-membered alkylene or alkenylene radical , n is 1 or 2, Z is halogen and R is alkyl of 1 to 4 carbon atoms or alkoxyalkyl of 2 to 5 carbon atoms , and Z is trifluoromethyl if X is haloalkoxy , wherein an amine of the formula (II) (II) where X , Y , Z and n have the above meanings , is reacted with a carboxylic acid chloride of the formula (III) Cl - CO - R (III) or an acid anhydride of the corresponding carboxylic acid , where R has the above meanings , in the presence of an acid acceptor and a solvent .