DE2405183A1 - HALOGEN ACETANILIDE AS PLANT CONTROLLING AGENTS - Google Patents

Description

Halogenacetanilides as plant-influencing agents

The present invention further relates to N-substituted haloacetanilides and processes for their preparation Plant-influencing agents that contain these new compounds as active ingredients, as well as methods for selective Using weed control in crops the new active ingredients or the agents containing them.

The following patents should be referred to as the state of the art on halogenacetanilides which have been known to affect plants to date: French patents 1,337,529, 1,419,116 and 2 28,991, Belgian patent 746 * 288 and US patents 2 ^S 863 '752, 3,442,945 and 3,547,620.

The object of this invention is to provide haloacetanilides with better plant-influencing properties To make available, i.e. those that, with small application rates, a larger number of weed species and before

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CIBA-GBGY AG

especially very resistant weeds, much better fight as the well-known Haolgenacetanilide, but without the crops intended for use adversely affect.

The novel N-substituted haloacetanilides according to the invention have chemical structural deviations of a fundamental nature to improve effectiveness the connections that have become known so far. They correspond to formula I.

A-OR

CO-CH ₂ X

R is an alkyl radical with a maximum of 3 carbon atoms, a Alkenyl radical with 3 or 4 carbon atoms, a cyclopropyl radical or a cyclopropylmethyl radical,

an unsubstituted ethylene chain (-CHp-CHp-) or a Ethylene chain monosubstituted by ethyl or mono- or disubstituted by methyl, Hydrogen or an alkyl radical with a maximum of 4 carbon atoms,

an alkyl radical with a maximum of 4 carbon atoms, and

independently of one another, one substituent each meta to the amine group, namely halogen, cyano, alkyl, Alkylthio or alkoxy each with a maximum of 3 carbon atoms, haloalkyl with 1 or 2 carbon atoms and

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CIBA-GEIGY AG _ 3 _

1 to 3 halogen atoms, alkoxyalkyl or alkylthioalkyl with 2 to 4 carbon atoms, and one of the substituents R-. or R ^ also hydrogen, and

X signify chlorine or bromine. .

Substituents which represent or contain an alkyl function are, depending on the definition Limitation, the lower members methyl, ethyl, propyl, isopropyl, Butyl, sec-butyl, isobutyl or tert-butyl are to be understood.

Alkenyl radicals mean the allyl group, the various methylallyl groups and the but-3-enyl group.

The term "halogen" includes fluorine, chlorine, bromine or iodine.

Under haloalkyl as defined, they are simple up to three times halogenated methyl or ethyl group to be understood, e.g. trichloromethyl, dichloromethyl, 1,2-dichloroethyl or trifluoromethyl.

Preferred active ingredients are compounds in which X is chlorine.

Of these, compounds whose substituents R and R _{p represent} alkyl radicals have in the majority of cases a particularly favorable spectrum of activity on useful plants and weeds. The total number of carbon atoms in both alkyl radicals R ₁ and R ₃ advantageously does not exceed the value

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CiBA-GEIGYAG - 4 -

A biologically interesting group of compounds are those in which A, R, R-,, R2 and X are those mentioned for formula I. Have meaning, and in which one of the substituents R "or R" meta to the amino group, chlorine, the cyano, Means trifluoromethyl, methoxy or methylthio group, and the other is hydrogen.

Among these, those compounds occupy a preferred position in which A is replaced by methyl or ethyl means monosubstituted ethylene chain.

Another group of compounds of biological interest and preferred for certain areas of application Formula I are those in which A and R have the meanings mentioned, X is chlorine, R is a methyl group represents, R «means hydrogen, methyl or ethyl, in which furthermore the substituent R "in the meta position to the amino group represents an alkyl radical with a maximum of 3 carbon atoms and R, is hydrogen.

In this last-mentioned group, those compounds which obey the formula I a are particularly preferred

-CH ₀ -O-R '

(la)

O -

wherein Rl is hydrogen, a methyl or ethyl group and R ¹ and Rt- independently of one another denote a methyl or ethyl group.

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Examples of such herbipids of the formula Ia with particularly favorable selectivity between crops and weeds

2,3-Dimethyl-N- (l'-methoxyprop-2'-yl) -N-chloroacetanilide, 2,3-dimethyl-N- (l'-methoxybut-2'-yl) -N-chloroacetanilide, 2, 3-dimethyl-6 ~ ethyl-N- (l'-methoxyprop-2 ¹ -yl) -N-chloroacetanilide, 2,3-dimethyl-6 ~ ethyl-N .- ( ^l- methoxybut-2 ^l -yl) -N-chloroacetanilide,

also the compounds of formula I.

2,6-Dimethyl-3-chloro-N- (2'-methoxyethy1) -N-chloroacetanilide, 2, ö-Dimethyl-S-chloro-N-Cl'-methoxyprop-2 ¹ -yl) -N-chloroacetanilide,

2,6-dimethyl-3-methoxy-N- (2'-methoxyethy1) -N-chloroacetanilide, 2,6-dimethyl-3-methoxy-N- (l'-methoxyprop-2 ^! Yl) -N-chloroacetanilide,

2,6-dimethyl-3-trifluoromethyl-N- (2'-methoxyethyl) -N-chloroacetanilide,

2,6-Dimethyl-3-trifluoromethyl-N- (1'-methoxyprop-2 ¹ -y I) -N-chloroacetanilide.

There are several variants, compounds of the formula I to establish, due to the possibility of the order different reaction steps' to change. Most of all, hits that for substitution reactions in the phenyl nucleus of the underlying aniline. However, one becomes advantageous first the substituents R, to R ^ have been introduced before the Carries out reactions on the amino group.

The new haloacetanilides of the formula I are according to the invention prepared by adding an N-substituted aniline of the formula II

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NH-A-OR

(II)

with a halogen acetylating agent, preferably an anhydride or halide of chloro- or bromo-acetic acid. In Formula II, R, R ^
Formula.I given meanings.

to R, and A the below

7) The compounds of the formula I can also be prepared in such a way that one by R 1 to R substituted aniline with optionally

- 2-haloethanol or ethylene oxide to introduce the hydroxyalkyl chain -CH ₂ -CH ₂ -OH, or

- 2-halopropanol to introduce the hydroxyalkyl chain

CH ₀

-CH - CH "- OH, or

- l »Kalogenpropan-2-ol or propylene oxide for introduction

CH ₃

the hydroxyalkyl chain -CH-CH-OH, or

- 3-halobutan-2-ol to introduce the hydroxyalkyl

CH ₀ CH ₀ 1 3 j 3

chain -CH — CH — OH, or

- 2-halobutan-1-ol to introduce the hydroxyalkyl chain

? 2 ^H 5

-CH - GH ₉ - OH, or

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CIDA-GEIGYAG - 7 -

- A corresponding haloalkanol to introduce a converts the other possible structural chains -A-OH, where "halogen" means chlorine or bromine,

then the resulting compound of the formula Ha

^R l

NH-A-OH (II a)

chloroacetylated or bromoacetylated, preferably with an anhydride or halide of chloroacetic acid or bromoacetic acid, and finally the still free OH group in an acidic medium (eg HCl, H ₉ SO,) under mild conditions in the usual way with an alcohol Rn-OH etherified, in which the radical R ~ corresponds to the definition given under formula I.

The reactions can be carried out in the presence or absence of a solution or solution which is inert towards the reactants Diluents are carried out. For example, the following are possible: aliphatic, aromatic or halogenated hydrocarbons such as benzene, toluene, xylenes, petroleum ether, chlorobenzene, methylene chloride, Ethylene chloride, chloroform; Ethereal and ethereal Compounds such as dialkyl ethers, dioxane, tetrahydrofuran; Nitriles such as acetonitrile; Ν, Ν-dialkylated amides such as Dimethylformamide; also dimethyl sulfoxide and mixtures these solvents with each other.

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Suitable haloacetylating agents are preferably haloacetic anhydrides, such as chloroacetic anhydride and haloacetic acid halides such as chloroacetyl chloride are used. However, the reaction can also be carried out with haloacetic acids, their esters or amides are carried out. The reaction temperatures are between 0 ° and 200 ° C, preferably between 20 and 100. In some cases, in particular When using haloacetyl halides, the haloacetylation is carried out in the presence of an acid-binding agent Carried out means. Tertiary amines such as trialkylamines, e.g. triethylamine, pyridine and pyridine bases, come as such. or inorganic bases, such as the oxides and hydroxides, hydrogen carbonates and carbonates of alkali and alkaline earth metals, into consideration. As an acid-binding agent can also the respective aniline of the formula II are used, which in this case must be used in excess.

Some starting materials of the formula II and corresponding hydroxyalkyl derivatives (R = H) are known, for example from USP 2,381,071, 2,759,943 and Atn.Soe. 84_, 734 and Bull. Soc.Chim. France 1962 , 303 and 1965 , 2037. These starting materials, as well as those not yet described in the literature and falling under the general formula II, can easily be prepared by methods known per se, such as, for example:

a) by condensation of the corresponding, through R ^ bis

R. substituted aniline of the formula III 4

(III)

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with a carbonyl compound IV

₅ s

0 = C-C-O-R IV

in which the substituents R ₁ -, Rg and R _{7 are} methyl or ethyl, but together have a maximum of 2 carbon atoms, while R has the meaning given for formula I, and simultaneous or subsequent catalytic hydrogenation of the azomethine of formula V obtained

ι ⁵ >

= C-C-O-R (V)

b) by reacting the aniline III correspondingly substituted by R 1 to R 1 with a compound of Formula VI

Y-A-OR VI

wherein A and R are as defined under formula I and Y represents a halogen atom or another acid residue, in particular an alkylsulfonic acid residue or an arylsulfonic acid residue. Compounds of the formula VI with benzenesulfonic acid radicals Y are, for example, in Can. J. Chem-33U 1207, those with tosyloxy radicals (CH ₃ -C ₆ H ₄ -SO ₃ -) in Brit. U.S. Patent No. 869,083;

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There are of course a number of other procedures for the preparation of the starting materials of the formula II from appropriately substituted anilines.

Alkyl-substituted anilines of the formula III can be used for Some of them can be obtained from natural raw materials such as coal tar, and some can be produced using known methods manufacture, some of which are mentioned here:

a) 2-alkylanilines or 2,6-dialkylanilines with C ^ -C ^ -alkyl groups in the ortho position of the phenyl nucleus can advantageously be obtained from the corresponding aniline with a C ₂ -C, alkene (e.g. ethylene, propylene, 1- Butene, 2-butene, etc.) under pressure in the presence of aluminum at over 200 ° C (Angew. Chemie 69_, 125 (1957). Obtain dimethyl-6-ethy aniline and with propylene 2,3-dimethyl-6-isopropyl aniline.

b) Starting from the corresponding toluene, ethylbenzene, isopropylbenzene, xylene, etc., meta-nitroanilines are obtained by dinitration and partial reduction, from which, by diasotation via the diazonium salts, meta-nitrohalobenzenes, meta-nitrocyanobenzenes, etc. are obtained, which are then passed through Reduction can be converted into corresponding anilines of the formula III (J.Chem.Soc. 1927 , 1106).

c) meta-alkoxyanilines are advantageous by alkylation the hydroxyl group of a meta-nitrophenol [J.Org. Chem. 2j5 ^ 4749 (1962)] and subsequent reduction of the nitro group manufactured.

d) m-Alkylthioanilines of the formula III are expedient by sulfo-chlorination of e.g. aeylated aniline,

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Reduction of the sulfonyl chloride group to the mercapto group and their alkylation obtained (British patent specification l'O27 ^f O6O).

e) m-Trifluoromethylanilines of the formula III are obtained for example from 2, (4) - (Di) Alky1-3,5-dinitrο-benzoic acid, partial reduction of the 5-position nitro group to the amino group, their diazotization and cleavage and subsequent Conversion of the carboxyl group into the trifluoromethyl group, whereupon the remaining nitro group becomes Amino group is reduced (British patent l'O27'O3O).

Some of the intermediate products important for this invention are mentioned here:

2,5-dimethyl-6-ethylaniline, b.p. 70-76 ° (0.7 Torr) 2,3-dimethyl-6-ethylaniline, b.p. 70-76 ° (0.7 Torr) 2,6-dimethyl-3-bromo (2 ^! -Ethoxyethyl) -aniline, boiling point 113-118 °

(0.5 Torr) 2,3,5,6-tetramethyl- (2'-methoxyethyl) aniline, b.p. 81-92 °

(O.OOlTorr)

2,3-Dimethyl- (2'-methoxyethyl) aniline, b.p. 73 ° (0.02 Torr) 2,3-Dimethyl- (1'-methoxyprop-2'-yl) aniline, bp 67-76

(O.OOlTorr) 2,3-dimethyl- (2'-ethoxyethyl) aniline, boiling point 82-86 °

(0.01 Torr) 2,3,5-trimethyl- (2'-methoxyethyl) aniline, boiling point 92 °

(0.3 Torr)

^{2,3,5-triethyl- (I 1} methoxyprop-2'-yl) aniline, boiling point 94 °

(0.5 Torr)

2,5-dimethyl-6-ethyl- (2 ^f -methoxyethyl) aniline, boiling point 95 °

(0.7 Torr)

2,5-dimethyl-6-ethyl- (2'-ethoxyethyl) aniline, boiling point 90 °

(0o4 Torr)

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2,5-dimethyl-6-ethyl- (2'-n-propoxyethyl) aniline, boiling point 98-105 °

(0.4 Torr) 2,5-dimethyl-6-ethyl- (2 ^l -isopropoxyethyl) aniline,

Bp 103-105 ° (0.6 Torr) 2,5-dimethyl-6-ethyl- (2 ^l -allyloxyethyl) aniline, bp 93 °

(0.1 Torr) 2,3-dimethyl-6-ethyl- (2'-methoxyethyl) aniline, boiling point 95 °

(0.7 ^ orr) 2,3-diethyl-6-ethyl- (2'-ethoxyethyl) aniline, b.p. 90 °

(0.4 Torr) 2,3-dimethyl-6-ethyl- (2'-n-propoxyethyl) aniline, boiling point 98-105 °

(0.4 Torr) 2,3-DimeChyl-6-ethyl- (2'-isopropoxyethyl) aniline,

Bp. 103-105 ° (0.6 Torr)

2,3-dimethyl-6-ethyl- (l'-methoxyprop-2'-yl) aniline,

Kp. 90-94 ° (0.8 Torr)

2,3-dimethyl-6-ethyl- (l '* - methoxyprop.-2' -yl) aniline,

Bp. 102-106 ° (0.6 Torr)

The following examples illustrate that according to the invention Process including the manufacture of raw materials. Further haloacetanilides of the formula I, that have been produced by one of the processes described are listed in the table below. Temperature data relate to degrees Celsius.

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example 1

a) 'A solution of 55.7 g (0.278 mol) of 3-Bro> ri-2,6-dimethylaniline and 34.0 g (0.139 mol) of p-toluenesulfonic acid (2-ethoxyethyl) ester in 100 ml of toluene are refluxed for 25 hours. After cooling, the reaction mixture is made alkaline, diluted with ether and the organic phase is washed several times with water. After evaporating the dried solution, vacuum distillation of the residue gives the desired product, N- (2 ¹ -aethoxy-ethyl) -3-bromo-2,6-dimethylaniline, with a boiling point of II3-II8 C / 0.5 Torr .

b) 'A suspension of 15.0 g (0.055 mol) of N- (2 ¹ -aethoxyaethyl) -3-bromo-2,6-dimethylaniline and 5.84 (0.055 mol) of soda in 60 ml of absolute ether is added dropwise with a A solution of 6.22 g (0.055 mol) of chloroacetyl chloride in 30 ml of absolute ether is added and the mixture is then stirred at J> 0 C for a further 3 hours. For working up, the reaction mixture is washed several times with water, dried and evaporated in vacuo. This gives the pure product, 2,6-dimethyl-3 ~ bromo-N- (2 ^f -aethoxyaethyl) -

20th

N-chloroacetanilide in quantitative yield; n ~ 1

[Verb. I].

Br

CO-CH Cl

4 U B ο j ζ / ι Ii

CIBA-GEIGYAG - 14 - Example 2

a) A solution of 847 g (7 moles) of 2,3-dimethylaniline and 855 g (3.5 moles) of p-toluenesulfonic acid (l'-methoxyprop-2'-yl) ester are poured into 3.8 liters for 25 hours Toluene refluxed. After cooling, the reaction mixture is made alkaline and the organic phase is washed several times with water. After evaporation of the dried solution, 69% (of theory) 2,3-dimethyl- (I ¹ -methoxyprop-2 ¹ -yl) -aniline, boiling point 67-76 ° C./0.001 torr, are obtained in the vacuum distillation.

Instead of using p-toluenesulphonic acid ester methoxyacetone also condensed with 2,3-dimethylaniline and the resulting azomethine is hydrogenated in absolute ethanol at normal pressure in the presence of palladium carbon will.

b) 15.5 g (0.08 mol) of the intermediate product obtained under a) are mixed in 100 ml of absolute ether with 8.5 g (0.08 mol) of sodium carbonate. A solution of 9.1 g (0.08 mol) of chloroacetyl chloride and 30 ml of absolute ether is added dropwise to this suspension, whereupon the mixture is stirred for a further 2 hours at room temperature. The organic phase is then washed three times with 50 ml of water each time. After drying the ether solution and removal of the ether left 14.3 g (-69 t of theory) of 2,3-dimethyl-N- (1'-methoxyprop-2 ^1-yl) -K-chloroacetanilide, m.p. 45-53 ° (Verb. 33) ·

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2) 2, 6-dimethyl-3-bromo-N- (2 ^l -methoxyäthyl) -N-chloroacetanilide,

3) 2,6-Dimethyl-j5-bromo-N- (2'-propoxyethyl) -N-chloroacetanilide _J.

4) 2, o-Dimethyl ^ -bromo-N- (2 * -isopropoxyethyl) -N-chloroacetanilide,

5) 2, 6-dimethyl-3-bromo-N- (2 '-cyclopropoxyäthyl) -N'-chloracetanilit'i, β) 2, 6-dimethyl-3-bromo-N- (2 ¹ -methoxypropyl) -N -chloracetanilide,

7) 2, 6-dimethyl-3-bromo-N- (2 'aethoxypropyl) -N-chloracetanilicl,

8) 2,6-dimethyl-3-bromo-N- (l'-methoxyprop-2'-yl) -N-chloroacetanilide,

9) 2,6-Dimethyl-3-bromo-N- (1'-ethoxyprop-2'-yli-N-chloroacetanilide.

10) 2, 6-dimethyl-3-bromo-N -. (3 '-methoxybut ^2-1 -ylJ-N-chloroacetanilide,

11) 2,6-Di! Nethyl-3-bromo-N- (2 ^L allyloxyethyl) -N-chloroacetane llide,

12) 2,6-diethyl-3-bromo-N- (2'-methallyloxyethyl) -N-chloroacetanilide,

13) 2 _J 6-dimethyl-3-bromo-N- (2 ^l -cyclopropylmethoxyethyl) -N-chloroacetanilide,.

14) 2, 6-Dlmethy 1-3-bromo-N- (2 '.- methoxyethyl) -N-bromacetanilidj

15) 2 _J 3,6-Trlmethyl-N- (2'-methoxyethyl) -N-chloroacetanilide,

16) 2 _J 3,6-trimethyl-N- (2 ^t -aethoxyethyl) -N-chloroacetanilide ,,

17) 2,3j6-trimethyl-N- (2'-isopropoxyethyl) -N-chloroacetanilide,

18) 2,3,6-trimethyl-N- (2'-methoxypropyl) -N-chloroacetanilide,

19) 2,3,6-trimethyl-N- (I ¹ -methoxyprop-2 ¹ -yl) -N-chloroacetanilide,

20) 2,3 _J 6-trimethyl-N- (2 ^I -cyclopropoxyethyl) -N-chloroacetanilide,

21) 2,3 _i 6-triethyl-N- (2'-methoxyethyl) -N-bromoacetanilide,

22) _{2,3,5-tetramethyl-i} 6 N- (2'-methoxyethyl) -N-chloroacetanilide, Fp.63 ^C

23) 2,3ί 5j 6-tetramethyl-N- (2-ethoxyethyl) -N-c.hloracetanilid,

24) 2,3,5j6-tetramethyl-N- (2 '-propoxyethyl) -N-chloroacetanilide ,,

25) 2,3,5j6-tetramethyl 1-N- (2'-isopropoxyethyl) -N-chloroacetanilidi

26) 2,3,5i6-tetramethyl-N- (2 ¹ -methoxypropyl) -N-chloroacetanilide, ■ - ⁵ .7) 2,3,5 _J 6-tetramethyl-N- (1 '-methoxyprop 2-yl ¹ ) -N-

chloracetanilide,

28) 2,3,5 * 6-tetramethyl-N- (l'-aethoxyprop-2 ^l -yl) -N-chloroacetanilide,

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29) 2,3-Di ^r N-ethyl-N- _(2'-T: ethoxyäVnyl) -N-chloroacetanilide, n 1.5351

/ Π

30) 2,3-Dimethyl-N- (2'-ethoxyethyl) -N-chloroacetariilide, n _D ^U 1.5223

31) ^2,3-D i ⁱ flethyl-N- (2 ^l -isopropoxyäthyl) -N-chloroacetanilide,

32) 2, 3-Dlrnethyl-N- (2 '-methoxypropy ^ -N-chloracetariilid.,

33) 2 _J 3-Dlmethyl-N- (1 ^I -methoxyprop-2'-yl) -N-chloroacetanilide, m.p. 45-53 ° 3 * 0 2, 3-Di ^r K ^f 2thyl-N- (2 ' -cyclopropoxyethyl) -N-chloroacetanllide,

35) 2,3-Dimethyl-N- (2'-allyloxyäthylJ-N-chloroacetanilide,

36) 2 _J 3-Dlmethyl-N- (2 ^! -Methoxyethyl) -N-bromoacetanilld,

37) 2,5-dimethyl-N- (2'-methoxyethyl-N-chloroacetanilide,

38) 2,5-dimethyl-N- (2'-ethoxyethylJ-N-chloroacetanilide,

39) ^ i 5-Dimethyl-K- (2'-aethoxypropyl) -N-chloroacetanilide,

40) 2 _JI 6-Dimethyl-3-chloro-N- (2 ^t -aethoxyethylJ-N-chloroacetanilide ^

4-1) 2,6-dimethyl-3-chloro-N- (2'-methoxyethyl) -N-chloroacetanilide, Mp. 52-55 °,

42) 2, 6-dimethyl-3-chloro-N- (2 ^f -propoxyäthylJ-N-chloroacetanilide,

43) 2 _J 6-diethyl-3-chloro-N- (2'-isqpropoxyethyl) -N-chloroacetanilide,

44) 2,6-Dimethyl-3-chloro-N- (2'-cyclopropoxyethylJ-N-chloroacetanilide,

45) 2 _J 6-dimethyl-3-chloro-N- (2 ^f -methoxypropyl) -N-chloroacetanilide,

46) 2,6-Dimethyl-3-chloro-N- (2'-aethoxypropylJ-N-chloroacetanilide, ·

4?) 2,6-DiT.ethyl-3-chloro-N- (l ^f -methoxyprop-2 ¹ -yl) -N-chloroacetanilide, melting point 54-56,

48) 2, 6-dimethyl-3-chloro-N- (l'-aethoxyprop-2'-yl) -N-chloroacetanilide,

49) 2,6-dimethyl-3-chloro-N- (3'-methoxybut-2'-yl) -N-chloroacetanilide,

50) 2., 6-DiT; ethyl-3-chloro-N- (2'-allyloxyethyl) -N-ehloracetanilidj

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51) _2-J 6 Ditnethyl-3-chloro-N- (2'-me-thallyloxyäthyl) -N-chloracetanllid,

52) 2, 6-dimethyl-3-chloro-N- (2'-cyclopropylmethoxyäthyl) -N-chloroacetanilide, ·

53) 2 _J 6-dimethyl-3-chloro-N- (2'methoxyethyl) -N-bromoacetanilide _J

54) 2-methyl-3-bromo-6-ethyl-N- (2'-ethoxyethyl / N-chloroacetanilide

55) 2-methyl-3-bromo-6-ethyl-N- (2'-methoxyethyl) -N-chloroacetanilide,

56) 2-methyl-3-bromo-6-ethyl-N- (2'-propoxyethyl) -N-chloroacetanilide,

57) 2-methyl-3-brora-6-ethyl-N- (2 ^f -isopropoxyethyl) -N-chloroacetanilide,

58) 2-methyl-3-b.rom-6-ethyl-N- (2 .'-cyclopropoxyethyI) -N-chloroacetanilide,

59) 2-methyl-3-bromo-6-ethyl-N- (2'-methoxypropyl) -N-chloroacetanilide,

60) 2-methyl-3-bromo-6-ethyl-N- (2'-ethoxypropylJ-N-chloroacetanilidj

61) 2-Kethyl-3-bromo-6-ethyl-N- (l'-methoxypr6p-2'-yl) -N- • chloracetanilide,

62) 2-methyl-3-bromo-6-ethyl-N- (l'-aethoxyprop-2'-chloroacetanilide,

63) 2-methyl-3-bromo-6-ethyl-N- (3'-methoxybut-2'-chloroacetanilide,

64) 2-methyl-3-bromo-6-ethyl-N- (2 ^t -allyloxyethyl) -N-chloroacetanilide,

65) 2-methyl-3-bromo-6-ethyl-N- (2'-methallyloxyethyl) -N-chloroacetanilide,

66) 2-Methyl-3-bromo-6-ether, hyl-N- (2 '-cyclopropylmefchoxyäthyI) -N .chloracetanilide,

67) 2-methyl-3-bromo-6-ethyl-N- (2'methoxyäthy "l) -N-bromoacetanilide,

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68) 2,6-Dimethyl-3-rciethoxy-N- (2'-methoxyethyl) -N-chloroacetanilide, Mp. 54-56 °,

69) 2,6-dimethyl-3-methoxy-N- (2'-ethoxyethyl) -N-chloroacetanilide,

70) 2,6-Diniethyl-3-methoxy-N- (2'-methoxypropyl) -N-chloraeetanilide,

71) 2 _J 6-dimethyl-3-methylthio-N- (2 ^t -methoxyethyl) -N-chloroacetanilide, m.p. 51-53,

72) 2,6-dimethyl- "3-methylthio-N- (2 '-aethoxyethyl) -N-chloroacetanilide,

73) 2,6-Dimethyl-3-methylthio-N- (l'-methoxyprop-2'-yl) -N-chloroacetanilici, M.p. 49-52,

74) 2,6-Dimethyl-3-eyano-N- (2'-methoxyethyl) -N-chloroacetanilide, m.p. 53-56,

75) 2,6-Di7iethyl-3-cyano-N- (2 ^l -aethoxyethyl) -N-chloroacetanilide,

76) 2,6-DiT! Ethyl-3-cyano-N- (2'-methoxypropylJ-N-chloroacetanilidj

77) 2,6-dimethyl-3-cyano-N- (l'-methoxyprop-2'-yl) -N-chloroacetanilide, M.p. 55-58,

78) 2 _J 6-dimethyl-3-trifluoromethyl-N- (2'-methoxyethyl) -N-chloroacetanilide (MP). 55-57 °,

79) 2,6-dimethyl-3-trifluoromethyl-N- (2 '-aethoxyethyl) -N-chloroacetanilide,

80) 2 _i 6-dimethyl-3-methoxymethyl-N- (2 ^l -methoxyethyl) -N-chloroacetanilidj

2, 6-DiTiethyl-3-methoxymethyl-N- (2 '-aethoxyäthyl) -N-chloraeetanilid,

4C9832 / 1 1 28

G - 19 -

82) 2 _J 6-diethyl-3-bromo-N- (2 ^l -aethoxyethyl) -N-chloroacetanilide _i

83) 2,6-diethyl-3-bromo-N- (2'-methoxyethyl) -N-chloroacetanilide,

84) 2,6-diethyl-3-bromo-N- (l'-methoxyprop-2'-yl) -N-ehloroacetanilide,

85) 2 _J 3-dimethyl-6-isopropyl-N- (2'-methoxyethyI) -N-chloroacetanilide,

86) 2,3-Dimethyl-6-isopropyl-N- (2'-ethoxyethyl) -N-chloroacetanilide,

87) 2,3-Dimethyl-6-isopropyl-N- (2'-methoxypropyl) -N-chloroacetanilide,

88) 2,3-dimethyl-6-isopropyl-N- (l'-methoxyprop-2 ^f -yl) -N-chloroacetanilide,

89) .2 _J 3-Dimethyl-6-isopropyl-N- (2 ^t -methoxyethyl) -N-bromo- '.

acetanilide.

90) 2,5-dimethyl-6-ethyl-N- (2'-methoxyethyl) -N-chloroacet » anilide, n ^ ° 1.5335,

91) 2,5-dimethyl-6-ethyl-N- (2'-ethoxyethyl) -N-chloroacet «

20 anilide, n £ ^u 1.5282,

92) 2,5-dimethyl-6-ethyl-N- (2'isopropoxyethyl) -N-chloro-

20th

acetanilide, η 1.5231,

93) 2,5-dimethyl-6-ethyl-N- ( ^l -methoxybut-2'-yl) -N-chloroacetanilide,

94) 2,5-dimethyl-6-ethyl-N- (2'-methoxypropyl) -N-chloroacetanilide,

95) 2,5-dimethyl-6-ethyl-N- (l'-methoxyprop-2'-yl) -N-chloroacetanilide,

96) 2,5-dimethyl-6 "" ethyl-N- (l '-aethoxyprop-2' -yl) -N-chloroacetanilide,

97) 2,5-dimethyl-6-ethyl-N- (2 -cyclopropoxyethyl) -N-chloroacetanilide,

409832/1128

75.11.399

CLBA-GEIGY AG - 20 -

98) 2,5-dimethyl-6-ethyl-N- (2'-propoxyethyl) -N-chloroacetanilide, n _D 1.5252,

99) 2,5-dimethyl-6-ethyl-N- (2'-allyloxyethyl) - N-chloroacetanilide, η 1.5357,

100) 2,6-dimethyl-3-methoxy-N- (l ^l -methoxyprop-2 ¹ -yl) -N-chloroacetanilide, m.p. 55-57,

101) 2,6-dimethyl-3-trifluoromethyl-N- (l'-methoxyprop-2'-yl) -N-chloroacetanilide, Mp. 55-59 °,

102) 2,5-dimethyl-N- (2'-methoxyethyl) -N-chloroacetanilide,

Mp. 42-45 °,

103) 2,5-dimethyl-N- (2'-ethoxyethyl) -N-chloroacetanilide,

ii ^ ° 1.5287,

104) 2,5-dimethyl-N- (2'-propoxyethyl) -N-chloroacetanilide,

n ^ ⁰ 1.5219,

105) 2,5-dimethyl-N- (2'-isopropoxyethyl) -N-chloroacetanilide,

Bp. 115-120 ° / 0.001 Torr.,

106) 2,5-dimethyl-N- (2 ^f -methoxypropyl) -N-chloroacetanilide,

n ^ ⁰ 1.5325,

107) 2,5-dimethyl-N- (l'-methoxyprop-2 ¹ -yl) -N-chloroacetanilide,

Mp. 44-46 °,

108) 2,5-0imethyl-N- (l'-ethoxyprop-2'-yl) -N-chloroacetanilide,

n ^ ° 1.5234,

109) 2,5-Dimethyl-N- (2'-eyelopropoxyethy1) -N-chloroacet

anilide, bp ^{118-123 β} / Ό. 001 Torr.,

110) 2 ₃ -Dimethyl-6-ethyl-N- (2 ^f -methoxyethyl) -N-chlorine

acetanilide, n_ 1.5335,

111) Z.S-Diniethyl-e-ethyl-H-ia'-ethoxyethyl) -N-chloroacet

anilide, nj: ⁰ 1.5282,

409832/1 128

ciBA-GEiGYAG - 21 -

112) 2,3-dimethyl-6-ethyl-N- (2 ^l -propoxyethyl) -N-chloroacet-

anilide, n ^ ° 1.5252,

113) 2,3-dimethyl-6-ethyl-N- (2 ^l -isopropoxyethyl) -N-chloro-

acetanilide, n ^ ° 1.5231,

114) 2,3-Dimethyl-6-ethyl-N- (2'-methoxypropyl) -N-ChloraCet-

anilide, n ^ ^u 1.5296,

115) 2,3-dimethyl-6-ethyl-N- (l'-methoxyprop-2'-yl) -N-chloro-

acetanilide, η ^ ^υ 1.5294,

116) 2,3-dimethyl-6-ethyl-N- (l'-ethoxyprop-2'-yl) -N-chloro-

acetanilide, n ^ ° 1.5217,

117) 2,3-D.imethyl-6-ethyl-N- (2 ^l -cyclopropoxyethyl) -N-chloro-

acetanilide,

118) 2,3-dimethyl-6-ethyl-N- (l'-propoxyprop-2 ¹ -yl) -N-chloro-

acetanilide,

119) 2,3-diethyl-6-ethyl-N- (l'-methoxybut-2'-yl) -N-chloro-

acetanilide, b.p. 122-128 ° / 0.00ITorr,

120) 2,3-dimethyl-6-ethyl-N- (2'-methoxybut-3 ¹ -yl) -N-chloro-

acetanilide, b.p. 138-143 ° / 0.002 Torr,

121) 2,3-dimethyl-6-ethyl-N- (l'-methoxy-2'-methylprop-2'-

yl) -N-chloroacetanilide, b.p. 132-136 ° / O.OOl Torr.

CI3A-GEIGYAG - 22 -

The active ingredients according to the invention are stable compounds and have very good herbicidal properties against gramineae and millet-like plants of the genera Setaria, Digitaria etc., against grasses such as Lolium species and also against dicot weed species such as Atnaranthus, Sesbania, Chrysanthemum, Galium, Pastinaca, etc., without damaging the crop intended for the use of the active ingredient. as Cultivated plants are soy, alfalfa, peas, lentils, peanuts, cotton, corn, coffee, tea, bananas, pineapples, Sugar beet, sugar cane, potatoes, peppers, tomatoes, spinach, onions, eggplants, sunflowers, tobacco, Brassica species like rapeseed and cabbage, but also cereal types like Called barley, oats, rye, wheat or dry rice and water rice.

The active ingredients are applied either before (preemergence) or after (postemergence) emergence the cultivated plants and the weeds and grass weeds, preferably before emergence. The application rates are between 0.1 and 10 kg of active ingredient per hectare, but being preemergent Already with an application rate of 0.2.5 kg AS / ha an extensive one Destruction of the weeds is achieved. To prevent weed infestation of railway embankments, factories, roads etc. to prevent it, one usually uses up to 10 kg of active ingredient per hectare.

In addition, the active ingredients of the formula I also show Growth-regulating properties by delaying the length growth of grasses (e.g. in existing lawn crops) and increase the tillering. Weeds that spread rapidly and quickly are inhibited from germinating and emerging and so removed from the crops of useful plants. The present acylated amines of formula I also have

4G9832 / 1128

CI3A-GEIGYAG - 23 -

defolating properties and can be used to delay flowering. The storage capacity of phytonutrients is usually improved by the active ingredients present. This is how, for example, the sugar content in sugar beets is determined and sugar cane or the starch content in potatoes or the fat content in soybeans or peanuts increased.

As already mentioned, are from the literature

herbicidal üiLogenacetanilide of comparable constitution known become. However, these either only have alkoxymethyl groups on the nitrogen atom (USP 3,547,620) or carry in an ortho position of the phenyl radical, other tertiary alkyl substituents, like in particular tert. Butyl (French Patent 1,337,529).

In the literature it is shown that the N-alkoxymethyl derivatives represent the top products and in any case the corresponding N-alkoxyethyl and N-alkoxypropyl derivatives are superior in terms of effectiveness (USP 3'5 ^ 7'620, example 85) · On the basis of this publication, the person skilled in the art had to assume that N-substituted haloacetanilides, polygamy have lower alkoxy, alkenyloxy and cycloalkoxy groups, which are bonded to the nitrogen atom of the anilide via alkylene radicals with 2 chain links, regardless of how they are are substituted in the phenyl nucleus, are out of the question as herbicides for practical purposes.

It has now been found, surprisingly, that the novel active ingredients of the formula I according to the invention which do not have the constitution allegedly most favorable for the herbicidal action in USP 3,547,620 and which are also substituted in the phenyl ring in at least one position meta to the amino group, these N- Alkoxy methyl -2, (6) - (di) alkyl -chloro acetanilide !! and others

409832/1128

ciBA-GBGYAG - 24 -

closely related compounds described in the literature are superior in selective weed control.

Example 3

Control of millet species and other monocotyledon weeds in various crops (pre-emergence method) .

One day after sowing the test plants in seed trays, dilute aqueous suspensions of the active ingredients are sprayed onto the surface of the earth in such concentrations that application rates of the equivalent of 2 kg, 1 kg and 0.5 kg per hectare are guaranteed. The seed trays are kept at 22 to 25 ° C and about 70 % relative humidity. The test is evaluated after 28 days according to the following index:

9 = plants undamaged (like control experiment)

1 = plants dead 8 - 2 = intermediate stages of damage - = not tested

Known halogen acetal compounds were used as comparison compounds.

anilide:

Comp. A = 2-methyl-N- (l'-methoxyprop-2 ¹ -yl) -N-chloroacet-

anilide (Frz. P. 2'028'991) Comp. B_ = 2, 6-diethyl ~ N- (methoxymethyl) -chloroacetanilide

(Commercial product) (USP. 3,547,620)

409332/1128

«I Ξ ο

ro co

to

O CM

Γ-!

il τ-Α

Corn oo I. ON ON ON α. OO oc ON I. . ON ON ο- ON wheat OO ON oo ON ON oc OO ON oo ON 1 ON barley ON oo ON OO ON he ON ON ON On ON ON CO ON ON soy OO ON ON ON ON OC ON ON ON ON ON ON ON ON cotton ON OO ON ON ON ON 00 ON ON On ON ON ON ON ON sugar beet OO ON ON ON ON r-l ON ON CO OO ON ON ON ON alfalfa i-l ON ON ON ON r-l oo CS T-A r-l ON ON ON tH LoIium r-l CS CS 1-1 CM CO r-l r-l r-l - iH CS iH iH CO Alopecurus t-l ^ CS t-l i-l CM t-l r-l CS r-l tH CS it r-l Cyperus r-l r-l CS i-l CS CO r-l r-l CS t-l CS tH tH tH Rottboellia t-l r-l r-l I. • r-l t-l r-l r-1 r-i CO tH tH iH Digitaria r-l r-l t-l r-l r-l r-l r-l r-l t-l tH tH iH iH tH r-l Setaria r-l r-l r-l r-l iH CS CS r-l i-l iH r-l tH tH tH tH Echinochloa CS i-l "O
d t-J - r-l O CS r-l iH tH d Application rate
in kg AS / ha r-l CM t-1 O r-l O
ON IO
O CS iH Verb. No. CM
CM ON
CS O
CO iH
On

CO Ü1

tr— LO O

M C

ω w 4J U O Em

CU

r-l CU

(ti

Corn oo OO ct ct O ^ CN CT CT CT CT CT CT oo CT CT CT CT CT wheat O CT CT σ CT CT CT LO οο CT CO VD CT CO <t CT barley CT CT ο σ- CO CT CT Γ> · CT CT LO · <) · OO CT soy ct ct CT CT CT CT CT CT CT 00 CT CT CO CT CT cotton CT ct ο CT CT CT CT co 00 CT 00 CT CT CT CT CT sugar beet CT CT CN CT CT CT CT CT CT CT CT LO <X) alfalfa I. ct , OO CO CT CT CT Ι-- CO CT r ^ Γ-- CT OO CT CT Lolium r-l ι τ-Ι τ- < τ-Ι CM CO γ-Ι r-l r-l CO <! ■ CM CNJ Alopecurus r-l CN CO CN ΐ-Ι I. I. r-l τ-Ι <l CN vO CM CO <! · Cyperus r-l τ- < CN «Η τ-Ι CM τ-Ι τ-Ι CS τ-Ι r-l r-l r-l CM LO CNl ¹ Rottboellia r-l τ-1 r-J τ-Ι τ- < T-I CNJ CO τ-Ι τ-Ι CO I-- CT CT LO Digitaria r-l i-l τ-Ι τΗ ι-Ι τ-Ι τ-Ι T-I r-l r-l r-l τ-Ι r-l τ-Ι r-l τ-Ι r-l r-l Setaria r-l r-l r-l τ-Ι r-l τ-Ι r-l τ-Ι τ-Ι r-l r-l H T-I t-t CO r-l r-l CNl Echinochloa CN τ-Ι 0.5 r-l CN
O 0.5 r-l T-I r-l r-l t- { H r- < r-l tH r-l r-l τ-Ι Application rate
in kg AS / ha r-l CN CN r-l 0.5 CN r-Ί 0.5 CN tH 0.5 CN r-l LO
m
O Verb. No. OC
O CT
CT CO
CO <J PQ

CO

CNl ro 00 CD O »4 ·

CIBA-GEIGY AG

From the comparative results, it can be seen that the selectivity of the compounds of the present invention with regard to the control of weeds and the protection of cultivated plants is significantly better than that of the closest comparable known compounds. In the practical application range of 1 kg The comparison compounds have active ingredient per hectare A and B do not have a satisfactory tolerance on crops, while on the other hand important weeds like Alopecurus, Lolium and Rottboellia are inadequately controlled.

Example 4 Control of weeds in rice

Rice (Oryza oryzoides) and weeds are sown in clay bowls with garden soil. The active ingredient solution was made from a 25% wettable powder and immediately after sowing on the earth

2 applied to the surface (amount of solution: 100 ml / m). the Trays were kept in the greenhouse at 24-27 and 70% relative humidity. The evaluation took place 28 days later according to the index given in Example 3.

Table 2

Verb.
No. Application rate
in kg AS / ha Cyperus
esculentus Setaria
italica Echino \
chloa eg rice 98 2
1
0.5 1
1
1 r-l r-l r-l 1
1
1 9 99 2
1
0.5 1
1
1 1
1
I. 1
1
Jn 8th
8th
9

409832/1128

ciBA-GEiGYAG - 28 -

Example 5 Growth inhibition in grasses (post-emergence method)

In plastic bowls with a soil-peat-sand mixture were placed
Sown seeds of the grasses Lolium perenne, Poa pratensis, Festuca ovina and Dactylis glomerata. After three weeks, the grasses that had emerged were up to 4 cm above the
Cut back the soil and sprayed with aqueous spray liquors of the active ingredients of the formula I 2 days later. The amount of active ingredient was the equivalent of 5 kg of active ingredient per hectare. 14 days after application, the growth of the grasses was evaluated according to the following linear grading scale:

Grade 1 = strong inhibition (no growth from application

Time)

Grade 9 = no inhibition (normal growth as untreated

Control)

Of the substances tested, very strong growth inhibition was achieved with the following compounds (grades 1 to 3): Nos. 29, 30, 33, 37, 41, 68, 71, 73, 78, 90, 95, 100, 102, 107 and 110.

409832/1 128

CIBA-GEI6Y AQ

The agents according to the invention are produced in a manner known per se, by intimate mixing and grinding of active ingredients of the general formula I with suitable ones Carriers and / or distribution agents, if appropriate with the addition of "additives inert to the active ingredients." Dispersion or solvents. The active ingredients "can in the following processing forms are available and used:

Fixed forms of processing: dust, grit,

Granulates, coated granulates,

. Impregnation granules and homogeneous

granules;

Active ingredient concentrates dispersible in water: wettable powder

(wettable powder), pastes, emulsions;

Liquid processing forms: solutions.

For the production of solid processing forms

(Dust, grit, granules) the active ingredients are mixed with solid carriers. Come as carriers e.g. kaolin, talc, bolus, loess, chalk, limestone, lime grit, attapulgite, dolomite, diatomaceous earth, precipitated silica Alkaline earth silicates, sodium and potassium aluminum silicates (feldspars and mica), calcium and magnesium sulfates., Magnesium oxide, ground plastics, fertilizers such as ammonium sulfates Ammonium phosphate, ammonium nitrate, urea. ground vegetable products such as grain flour, tree beef, Wood flour, nut shell flour, cellulose powder, residues from plant extractions, activated charcoal, etc., either individually or as Mixtures with each other in question.

The grain size of the carrier material for dust is appropriately up to 0.1 iv.m _s for grit approx =

0.075 to 0.2 mm and for granulates 0.2 pns oc-sz ³ more =

409832 / 112S-

CIBA-GEIGYAG

The active ingredient concentrations in the solid working-up forms are 0.1 to 80 %.

These mixtures can also contain the active ingredient

■ stabilizing additives and / or non-ionic, anion-active and cationic substances are added, for example improve the adhesion of the active ingredients to plants and parts of plants (adhesives and adhesives) and / or ensure better wettability (wetting agents) and dispersibility (dispersants). As an adhesive For example, the following are possible: olein-lime mixture, cellulose derivatives (methyl cellulose, carboxymethyl cellulose), Hydroxyethylene glycol ethers of mono- and dial-, kylphenolen with 5-15 ethylene oxide residues per molecule and 8-9 carbon atoms in the alkyl radical, lignin sulfonic acid, their alkali and alkaline earth salts, polyethylene glycol ethers (Carbowaxe), fatty alcohol polyglycol ethers with 5-20 ethylene oxide residues per molecule and 8 - 18 carbon atoms in the fatty alcohol part, condensation products of ethylene oxide, Propylene oxide, polyvinylpyrrolidones, polyvinyl alcohols, condensation products, urea-formaldehyde and Latex products.

Active ingredient concentrates dispersible in water, i.e. wettable powders, pastes and emulsion concentrates are agents that react with water on each desired concentration can be diluted. They consist of an active ingredient, a carrier and, if applicable, the active ingredient stabilizing additives, surface-active substances and antifoams and, if necessary, solvents. The active ingredient concentration in these agents is 5 -

409832/1 128

CIBA-GEIGY AG

The wettable powders and pastes are obtained by mixing the active ingredients with dispersants and powdery carriers in suitable devices mixed and ground until homogeneous. The above for the solid work-up forms mentioned in question. In some In some cases it is advantageous to use mixtures of different carriers. As dispersants, for example are used: condensation products of sulfonated naphthalene and sulfonated naphthalene derivatives with Formaldehyde, condensation products of naphthalene or '' of naphthalenesulfonic acids with phenol and formaldehyde as well as alkali, ammonium and alkaline earth salts of ligninsulfonic acid, further alkylarylsulfonates, alkali and alkaline earth metal salts 'of dibutylnaphthalene sulfonic acid, fatty alcohol sulfates such as salts of sulfated hexadecanols, heptadecanols, octadecanols and salts of sulfated fatty alcohol glycol ether, the sodium salt of oleyl methyl tauride, ditertiary acetylene glycols, Dialkyldilaurylammonium chloride and fatty acid alkali and alkaline earth salts.

Silicones, for example, can be used as antifoam agents.

; The active ingredients are mixed, ground, sieved and passed with the additives listed above in such a way that ■ In the case of wettable powders, the solid fraction does not exceed a particle size of 0.02 to 0.0 ^ - and in the case of pastes it does not exceed 0.03 mm. For the production of emulsion concentrates and pastes, dispersants as described in the preceding Sections listed were organic solvents and water used. Examples of solvents are used the following in question alcohols, benzene, xylenes, toluene, dimethyl sulfoxide, Ν, Ν-dialkylated amides, N-Qxides of A

409832/1128

CLBA-GEIGY AG

in particular trialkylamines, and mineral oil fractions boiling in the range from 120 ° to 350 °. The solvents must practically odorless, not phytotoxic, inert to the active ingredients and must not have a too low flash point own.

The agents according to the invention can also be used in Form of solutions can be applied. For this purpose, the active ingredient or several active ingredients of the general formula I are used in suitable organic solvents, solvent mixtures, water or mixtures of organic solvents dissolved with water. Aliphatic solvents can be used as organic solvents and aromatic hydrocarbons, their chlorinated derivatives, alky! naphthalenes, mineral oils alone or as Mixture with each other can be used. The solutions are said to have the active ingredients in a concentration range of $ 1 to $ 20 'contain. These solutions can either be done with the help of a Propellant gas (as a spray) or with special syringes (as an aerosol).

Other biocidal active ingredients or agents can be admixed with the agents according to the invention described. Thus, in addition to the compounds of general formula I mentioned, the new agents can e.g. insecticides, fungicides, bactericides, Contain fungistats, bacteriostats, nematocides or other herbicides to broaden the spectrum of activity.

As herbicidal or plant growth influencing Combination partners are countered by the following known active ingredients :

409832/1128

CIBA-GEIGYAG

A) Substituted ureas

■! N-phenyl-N'jN'-diinethylurea

! N-pheny] -N-hydroxy-N ', N'-difethylurea

■ N- (4-chlorophenyl) -N ", N'-diBiethy] urea

; N-O.A-dichlorophenyiH'.N'-dinethylurea

N- (3,4-dichlorophenyl) -N-benzoyl-N ', N' -dimethy! Urea ι
. N- (I-chlorophenyO-N'-methoxy-N'-methylurea

. N - (^ - chloropheny1) -N'-i sobutinyl-N'-methylurea N-O ^ -DichlorophenylJ-N'-niethoxy-N'-fflethylurea N- (4-3rorophenyl J-N'-raethoxy-N'-riethylurea f N-U - (^ - chlorophenoxy) phenyl] -N ', N'-di »ethylurea

'N-Benzthiazol-2-yl-N, N'-dimethylurea N-Benzthiazol-Z-yl-N'-Biethylurea N- (3-trifluoromethyl-4-methoxyphenyI) -N ¹ , N'-dimethyl urea N- iS-Trifluorraethym-isopropoxyphenylJ-N'jN'-dimethylurea N- (3-Trif! uormet hy lpheny I) -N ', N' -diniethy lurea N - ^ - TrifluormethylphenyU-NSN'-diinethylurea NO.'t-DichlorphenylJ- N'-methyl-N'-butylurea N- (3-Ch] oM-trif] uorraethy lpheny I) -N ¹ , N'-dimethy lurea i NO-chloro-'i-ethylphenyD-N'jN'-dimethylurea \ N- (3-l ^ chloro-4-methylpheny 1) -N ', N'-dimethylurea

N-O-Ch 1 οΓ-4-ethoxyphenyl) -N '-nethy 1-N' - «ethoxyurea f ! N-O-ChloM-methoxyphenylMSN'-dimethyl urea

'N- (Hexahydro-i, 7- «ethanoindan-5-yl H ¹ , N'-diwthylurea, N- (2-methylcyclohexyl) -N'-phenylurea

N'-Cyclooctyl-N.N-diiaethylurea -

Oichloral urea

N '- [4 - (^' - Hethoxyphenoxy) -phenyl] -N, N-dimethylurea N'-0-methylphenyl) -N, N-diraethylthiourea ■ N, N-Din) ethyl-N '- [3- {N-tert ₀ butylcarbaisoyloxy) phenyl urea ¹ OjN.N-trimethyl-N '.- ^ - chlorphonylisoharnstoff

409832 / 1.1

red

CiBA-GEIGYAG - 34 -

H, N ^r -Oiwethyl-K'-phenyl urea f-trichloroacetate

! N, N-Oinethyl-NM-chlorophenyl-urea-tri-chloroacetate ι *

K- (4-isopropylphenyl) -N ', N'-dimethylurea'! N- [3- (1 ^f , I ¹ , 2 ^I , 2 ^I -tetrafluoroethoxy) phenyl] -N ¹ , N ¹ -diiiiethy] urea N- (3-chloro-i-trifluorohoxy-phenylJ-N'jN'-dimethylurea ίί-Αηί] inocarbonyl-2,5-diraethy] pyrrolidine -N ^ -di-tert-butylcarbanioyloxyJ-phenyl-N'-raethyl-N '-fliethoxy-urea H- (3 _f ^ -0ichlorpheny]) - N'-n-propylurea N-iS-ChloM-trifluonnethyl-phenyU-N'-methyl-N'-iBethoxyurea NO-Oi fluorochloromethyl-phenylJ-N'-eiethyl-N'-fflethoxyurstoff'li-la-d'.l' ^ '- Trifluor-Z'-chloro-ethoxyJ-phenyll-N'-nethyl-N'Hiethoxyharnetoff N-C3-Chlor - ^ - brofliphenyl) - N '-'ethyl-N'-methoxyurea K- (3-chloro - ^ - i sopropylpheny 1) -N '-iaethy lN ^L methoxyharnstof f' li- [5-Trifluoniie-thyl-l, 3, <- thiadiazole ( 2) -yl] -N, N'-diiiiethylharn8toff N- [5-0ii "ethylsulfaflioyl-l _l 3 ^ -thiadiazol- (2) -yl] -N _f N ^I -diiiiethylharnstoff H- [3- (N-tert .Butylcarbaraoyloxy) -phenyl] -N'-methyl-urea

M-II- or 2- (3a, 4,5,6,7,7a-hexahydro-4,7-methanoindanyl)] - K ·, K'-di »ethy! -Urea

M-fluorophenyl-N'-carboxynethoxy-N'-fflethyl-urea laidazolidine-Z-Ofi-l-carboxylic acid isobutylawid: N- (3-chloro-4-raethoxypheny]) - N'-methoxy-N ^t -methy] -urea

40983 2/1128

too. · * ·: ·

CLBA-GEiGYAG

B) Substituted triazines

2-chloro-A, 6-bis (äthylamino) -s-triazine 2-chloro - ^ - ethylamino-6-i sopropylaraino-s-triazine 2-methoxy-A, 6-bis (isopropylami no) -s -tri azi η 2-methylmercapto- ^/ i, 6-bis (isopropylaiiiino) -s-thazine 2-trtethy lmercapto-1,6-bis (äthylaoii no) -s-tri azi η Z-methylmercapto - ^ - äthylafflino- 6-tert.butylaiiiino-triazine 2-diethylmercapto-'i-ethylamino-6-isopropylamino-s-triazine Z-methylraercapto - ^ - methylafflino-β-isopropylanino-s-triazine 2-methoxy-4,6-bis (ethylamino ) -s-triazine 2-methoxy-4-äthy1 am i no-6-i sopropy1 am i no-s-tri azi η 2-chloro - ^, 6-bi s (i sopropy1 ami no) -s-tri azi η Z-Azido-'i-methylraercapto-ö-i sopropy 1 ami no-s-tri azi η 2-Azido-4-methylmercapto-6-sec.butylamino-s-triazine 2-chloro-A-isopropylaraino-6- (Y-methoxypropylaBiino) -s-triazine Z- (6-ethylamino-4-chloro-s-triazin-2-yl-amino) -2-fflethylpropionitrile Z-chloro-A-diethylaraino-6-isopropylamino-s-triazine 2 -Methylmercapto - ^ - i sopropy lamino-6- (3'-ffletho) (propylai »ino) -s-triazine 2-chloro-4-di äthy1 amino-6-äthyiamino-s-triazine 2, A- Bi (3'-iiiethoxypropylamino) -6-raethyl (iiercapto-s-triazine 2-chloro - ^ - äthy1 ami no-6-sec.butylam i no-s-tri azi η 2-chloro-4-cyclopropylafiiino-6- i sopropylamino-s-triazine Z-methylthio-4-ethylamino-6-sec.butylamino-s-triazine Z-methylthio-i-isopropylaRino-o-tert.butylamino-s-triazine 2-azido-A-eth: hylaniino -6-tert.butylamino-s-triazine A-amino-ö-tert.butyl-S-methylthio-i, 2,4-triazine-5 - (^ iH) -one 2-methylthio-A-ä-thylamino- 6- (l ', 2'-dimethyl-propylamino) -s-triazine! 2-trifluoromethyl-'i-äthylafflino-6-! 5opropylamino-s-triazine 2-trifluoromethyl-4,6-bis (ethylamino) -s-triazine '2-ethoxy-4-ethy1ainino-6-tert.butylafflino-s- triazine

, 2-methoxy-4-ethyla »ino-6-sec.butylaiaino-s-triazine 2-ethylthio- <i, 6-bis (isopropyla «ino) -s-triazine

409832/1 1 28

/HIM "'·:*

CiBA-GEIGYAG

ι 2-Ch IΟΓ-4-ae thy 1 ani no-6-tert .buty1 a «i no-s-triazi η

2- (6 ^l -cyclopropyla "ino-4'-chloro-s-triamine-Z ^l -yl-a" ino) -Z- "ethyl-propionitrile 2-Xethylthio-4-i6opropyla" ino - & - sec.butyla «Ino-s-triazine

C) phenols

ZjA-Oinitro-e-sec.butylphenol salts + ester

Pentachlorophenol or salts thereof
4,6-nitro-o-cresol

2,6-Di bromo - ^ - cyanopheno 1 + ester

2,6-dichloro-4-cyanophenol salts 4 esters

2,4-0initro-6-tert-butylphenol salts + esters

Z ^ -Oinitro-ö-sec.amylphenol salts + esters

Z-tert.8uty] -1,6-denitro-5- «ethylphenol salts + esters

2,6-0 ij od-4-cyano-pheno1
2,3,5-trichloro-4-hydroxypyridine
3,5-0ichloro-2,6-difluoro-4-hydroxypyridine
¹ Z ^ -Dinitro-B-sec.butyW '^' - dinitrodiphenyl carbonate
Z. ^ S-trichloro-6-nitro-phenyl chloroacetate
2-isopropy] - ^, 6-dinitro-phenol, salts and esters

AO 98 32/1 128

70 O- ι "i

CLBA-GEIGY AG _ 37 _

D) carboxylic acids, salts, esters and amides

2,3,6-trichlorophenylacetic acid 2,3,6-trichlorobenzoic acid and salts 2,3,5,6-tetrachlorobenzoic acid and salts ¹ 2,3,5,6-tetrachloroterephthalic acid + ester

2-methoxy-3,5,6-trichlorobenzoic acid and salts • 24iethoxy-3,6-dichlorobenzoic acid and salts ·

i 3-amino! -2,5-dichlorobenzoic acid and salts · _; 3-nitro-2,5-dichlorobenzoic acid and salts: 2-methyl-3,6-dichlorobenzoic acid and salts: 2,4-di.chlorophenoxyacetic acid, salts and esters 2,4,5-trichlorophenoxyacetic acid, salts and esters 2-methyl chlorophenoxyacetic acid, salts and esters 2- (2 ', V, 5'-trichlorophenoxy) propionic acid, salts and esters 2- (2 ^l , 4 ^l , 5'-trichlorophenoxy) ethyl-a, a-dichloropropionate ^ - (2 ', ^' - dichlorophenoxy) butyric acid, salts and esters 4- (2'-methyl-4'-ch! Orphenoxy) butyric acid, salts and esters methyl-2-chloro-3- (4'-chlorophenyl) propionate I 2-chloro-9-hydroxy-fluorene-9-carboxylic acid and ester '. 3,6-endo-oxo-hexyhydrophthalic acid and salts i ^ -Chlor ^ -oxobenzothiazolin-S-yl-acetic acid, 2,2,3-trichloropropionic acid, salts and esters! 2,2-dichloropropionic acid, salts and esters] 2- (2 ', 4'-0ichlorophenoxy) propionic acid, salts and esters I' i-chlorophenoxyacetic acid, salts and esters ι gibberel1insäure
i 2- ( ^/ i'-chloro-2 ^l -methylphenoxy) propionic acid, salts and esters

i Ν, Ν-tiallyl chloroacetamide I a-fiaphthy lessi gic acid

^! N-1-Naphthyl-phthalic acid, salts and esters' ^ -Amino-a.Sje-trichloro-pJceHic acid, salts and esters Trichloroacetic acid

409832/1128

7o.ai.aas

CiBA-GEIGYAG - 38 -

ι i-CZ'j ^ 'jS'-TrichlorophenoxyJbutyric acid, salts and esters i2,3,5-triiodobenzoic acid, salts and esters Benzaido-oxyacetic acid, salts and esters : Ethylene glycol bis trichloroacetate ! Chloracetic acid diethylanide '2,6-Oichlorthiobenzanid

2,6-dichlorobenzonitrile

N ₁ fi-Dinethyl-ii, a-diphenyl acetamide Diphenylacetonitri1 N-Hydroxyethyl-Zjo-dichlorothiobenzaniid

2,3,5,6-Tetrachlorothioterephthalic acid-0, S-diethyl ester 2,3,5 _f 6-tetrachloro-N-ethoxyTN- "ethyl-terephthalic acid-" ethyl ester-aaid iJ-Hydroxy-fluorene-II-carboxylic acid and esters n-Naphthoxy-acetic acid, ethyl ester ß-Naphthoxy-acetic acid- «ethy! ester 2- (l-naphthoxy) -N, N-diethylpropionamide 2- (2'-methyl-4'-chloro-phenoxy) -N-iaethoxy-aceta «id

N- (l ', l'-0Jiiethyl-propynyl) -3,5-dichlorobenzaiijd

ilonoch I or edible acid

2,2,3,3-tetrafluoropropionic acid, salts and esters 2- (iietnoxy-3,6-dichloro-pheny] acetic acid and salts succinic acid-aono-NjN-diiethylhydrazide 2,2-l) chloro-butyric acid and salts S. -Cnlor- ^ - iiethyl-Z-propionyl-afliino-thiazole N- (2 "-Butoxyethyl) -2'-chloro-N- (2,6-diethyl-1-cyclohexen-J-yl) acetateJd

(^ -Hethyl - ^ - chlorophenoxyJ-thioacetic acid-S-ethyl ester cis-S-chloroacrylic acid and salts , A-chlorophenoxy-acetic acid and salts and esters 2- (2'-ethyl-phenoxy) -propionic acid j ^ -Oichlorphenoxy-thioessigsä'ureanid Trichlorophenyl-acetonitrile

409832/1 1

CiBA-GElGY AG

E) carbamic acid derivatives ί

————___________ _i j

n-Tri-fluoromethyl-carbanic acid-isopropyl ester

I '- I

2,6-Di-tert.butyM-tolyl-N-methylcarbamate ί

j

; S-itfethoxycarbonylaminoJphenyl-N-S-tolylcarbaate

• i-chloro ^ -butynyl-NO-chlorophenyO-carbaiate ^; Ethyl-N - (^ - Aniinobenzsulfonyl) -carba »at sec.Butyl-NU-chlorophenylJcarbamat Isopropyl-N- (3-chlorophenyl) -carbamat SZ ^ -Dichlorallyl-N ^ -diisopropylthiolcarbaaat S-Ethyl-NjN-dipocarbiolditharbiolcarbanat and salts S-propyl-N-butyl-N-ethylthiol carbamate isopropyl N-phenycarbamate
2-ChloralIyI-N, N-diethyldithiocarbamate methyl-N- (3,4-dichlorophenyl) carbaisat S-2,3,3-Trichlorally] -N _t N-di-propyl-S isopropylthiolcarbanat NjNj dipropylthiolcarbamat-S-ethyl-N -ethyl-N-cyclohexyl-thiolcarbanate 3,4-dichlorobenzyl-iiiethylcarbaniate S-ethyl-N-hexahydro-1H-azepine-1-carbothioate 'Hethyl-N- (4-nitrobenzsulfonyl) carbaniate ¹ NjN-hexamethylene-S-isopropyl- thiolcarbaniate; S-ethyl-NjN-diisobutylthiolcarbaraat Ϊ Uethyi-N-Ci-methoxycarbanioyl-benzsulfonyUcarbafflat: N-ethyl-2- (phenyl-carbamoyloxy) -propionamide i NO-chlorophenylJ-carbamic acid-butyn-1-yl-S-ester. '! 3- {propiony1 aminopheny1) -Nisopropylcarbamate; N _f K-diethyl S- ( ^/ i-chlorobenzyl) thiol carbamate; N-Ethylthiocarbonyl-cis-decahydroquinoline S-Ethy1-N-cyc1opropylmethy1-N-propy1-thiolcarbanate N-Propylthiocarbonyl-decahydroquininaldine Ν, Ν-Di-n-butyl-S-ethyl-thiol-S-Oip-tert.-Oip., .butyl-thioicarbaaat

409832/1

70.01.33S

CIBA-GEIGY AG - 40 ""

I;

■ F) anilides!

3,4-olichloropropionanilide

3-chloro-A-bromopropionanilide

3-bromo-i-chloropropionanilide

Cyclopropanecarboxylic acid S ^ dichloroanilide Cyclopropanecarboxylic acid-S-chloro-i-broiiiani lid Cyc 1 opropanecarboxylic acid - ^ - brodi-A-ch lorani 1 i d N-iSji-dichlorophenylJ-Z-methylpentanecarboxylic acid aiide N- (3-tolyl) phthalic acid

2-methacrylic acid-3 ', ^ ^f -dichloro-anilide N- (A-chlorophenyl) -Z, 2-di * ethylvaleraBid NO-chloro-A-HBethylphenyD-Z-iiiethylpentanecarboxylic acid-aiiid Z-chloro-N-iZ'- methyl-e'-tert.butylphenylJacetaaid Z-ChlflCjo-N-iZ '^' - diethylphenylJ-N-ethoxyaethyl-acetanilide o-tdethyl-N-HiethoxyBethyi-Zt-butyl-a-bronacetanilide 2-Chloi-N-isopropyl-acetanilide

N-ia ^ -OichlorphenyD-N-benzoyl-Z-aminopropionic acid ethyl ester

N-Isopropoxyiaethyl-Z-chloro-Z '^' - diBethylacetanilid N-ethoxyniethyl-Z-chloro-Z'-ethyl-e'-ethyl-acetanilide N-n-Butoxymethyl-Z-chloro-Z '^' - diethylacetanilide Z-Bethyl - ^ - chlorophenoxyacetic acid-Z'-chloro-anilide N-Isobutoxyiiiethyl-i-chloroacet-Z.ö-d-Diethylanilid

409832/1128

7OO1.3M

CLBA-GEIGY AG - 41 -

_i 24,911 8 3

j G) Organic phosphorus compounds. ι

y y

tris- (2, A-dichlorophenoxyethyl) phosphite!

I o- (Z, 4-dichlorophenyl) -0'-uethyl-N-isopropyl-a-di-thiophosphate j

I I

'N- [2- (0,0-0i-isopropy "ldithiophosphoryl) ethyl] benzo1sulfonaBide'

S, S, S-tributyl trithiophosphate
- 2,4-dichlorobenzyl-tributyl-phosphonium chloride ^: 2-chloroethane phosphonic acid
'Tributyl trithiophosphite

N- (O ₁ O-Di-n-propyl-dithiophosphoryl-acetylJ-hexaBethyleneiBiη N- (O ₁ O-Oi-n-propyl-dithiophosphoryl-acetylJ-Z-Bethyl-piperidine, N-phosphonoinethyl-glycine and salts
¹ N, N-bis (PhosphonoBethyl) -glycine and salts 0- ( 2-N i tro-A-nethy1-pheny1) -0'-ethy1-Nt sopropy1-an i dothiophosphate

409832/1128

70th at 335th

CiBA-GElGYAG "42"

ι H) Various connections · .ι

-Z-trifluoromethylbenziaidazole ι

; Z-Chlorethyl-trifflethyl-aufsoniuBchlorid ι

J maleic hydrazide;

Methylarsinic acid di-Na salt

■ A, 5,7-trichlorobenzthiodiazo] -2,1,3 ' 3-alpha-1,2,4-triazole

Trichlorobenzyl chloride

2-phenyl-3, l-benzoxazin-4-one

ι 'N-ßutyl-N-ethyl-2,6-dinitro-i-trifluomethylaniline

■ N, N-0i- (n-propyl) -2,6-dinitro-4-trifluoriethylaniline ^ -TrifluomietBy1-2, h '-dinitro-diphenylether 2, S6-trichloro-4'-nitrodiphenylether A-trifluomethyl ^^'dinitro-S'-uethyl-diphenyl ether 2,4-dichloro-A'-nitro-diphenyl ether S-chloro-.delta.-ethyl-S-tert.butyluraci1 Ammoni utnsul f Amat

S-Broie-B-aethyl-S-secbutyl-uracil 5-Bro "-3-i sopropyl-oennethyluraci 1 S-cyclohexyl-S ^ -trimethylene-uraci 1 2,3,6-trichlorobenzyloxy-propanoH2 ') hexachoro-2 -propanon

Sodium 2- (2 ', ^, 5'-trichlorophenoxy) -äthy1su1 fat Potash cyanate

SjS-Dibrow - ^ - hydroxybenzaldoxiBi-Z ¹ , ^ ¹ dinitrophenylether '3,5-Di iodo-4-hydroxybenzaldoxiH-2', 4'-dinitrophenylather : Aero lein

Allyl alcohol

2, i-Dinitrophenyl-2 ', 4 ^l -dinitro-6 ^l -sec.butylphenyl-carbonate 5-chloro-Z-isopropylbenziBiidazoi 5-iodo-2-trifluoroniethylbenziaidazole l, r-ethylene-2,2'-bipyridyliuebroi " id

A09832 / 1 1

C (BA-GEIGYAG ~ ^HJ ~

1,1'-dimethyl-A, A'-bipyridyl dimethyl sulfate

Oi (methoxythiocarbonyl) disulfide j

Z-methyl-4- (3'-trifluoromethylphenyl) -tetrahydro-l, Z, 4-oxadiazine-3,5-dione '

l-phenyl-1,5-dimethoxy-B-pyridazon · j

• ι

6-chloro-2-trifluoromethyl-3H-imidazo (A, 5-b) -pyridine i

Z-tert-Butyl-6-chloro-3H-iaiidazo (^, 5-b) -pyridine 5 — Am i no-1-bromo-Z-pheny 1 pyri dazi n-3-one hexafluoroacetone trihydrate SjS-Oinitro-'i-dipropylamino-benzenesulfonafflide Cacodylic acid and salts

4- (methylsulphonyl) -2,6-dinitro-N, N-dipropylaniline '

S-Amino - ^ - chlor-Z-phenylpyridazin-3-one ^, Se-Tetrahydro-SS-dimethyl-ZH-l.SjS-thiadiazine-Z-thione sodium 2- {2 ', Ί'-dichlorophenoxy) - athylsulfat 2,3-di chloro ^ A-naphthoquinone di (äthoxythiocarbonyl) disulfide 'i tri f trifluoromethyl-3-amino-2,6-dinitro-N, N-diethyl-N-ani lin 2,6-0initro , N-di- (Z'-chloroethyl) -p-toluidine K-sec.Buty1-A-tert.buty1-2,6-di nitro-ani1i η N-propyl-N-cyclopropylfflBthyl-mifluoromethyl-zjo-dinitro -aniline N-propyl-N-Z'-chloroethyl-Z ^ -dinitro-A-trifluoro-ethyl-anUin copper sulfate

Iron sulfate

Sodium chlorate

O- (N-Pheny1carbamoy1) -propanon-oxi m ^ '- Nitro-2, A-dichloro-6-fluoro-diphenyl ether !, l-dimethyl- ^ ß-diisopropyl-S- or T-indanyl-ethyl-ketone l- (2 ', Z'-Dimethyl-S'-acetoxy-propionyli-S-isopropyl ^^ - dioxo-deca-

hydroquinazoline,

N- [1-phenyl-5-broin-pyridazon-6-y 1-Ci)] oxamic acid and salts. ;

S-tert-butyl-S-broni-B-methyl-uraci 1 ■

'■ Z-Methyl-AiA'-fluorophenyl) tetrahydro-1,2, A-oxadiazine-3,5-dione. _:

3-Isopropyl-Z, l _f 3-benzothiadiaz5n - ^ - on-Z, 2-dioxide!

A09832 / 1128

CIBA-GEIGY AG - 44 -

2-ethoxy-2,3-dihydro-3,3-diniethyl-5-ben2ofuranyiHRethanesulfonate

a- (2,2,2-trichloroethyl) styrene

2- (3 ', Ί'-Dichlorophenyl) - ^ - methyl-3,5-di oxo-i, 2,4-oxadiazole A-chloro-5-methylainino-2- (3'-trifluoroinethyl-phenyl ) -3 (2H) -pyridazinon A-fluor-5-dimethylamino-2- (3'-trifluoromethyl-phenyl) -3 (ZH) pyridazinone

'3- (2'-Wethylphenoxy) pyridazine A-isopropyl-2,6-dinitro-N, N-dipropylaniline -

3- (2'-Tetrahydropyranyl) -5,6-tri «ethylene uracil 5-chloro-3- (2'-tetrahydropyranyl) -6- «ethyl-uracil

In the following, working-up forms of the new active ingredients of the general formula I are described. Parts mean parts by weight.

409832/1128

CIBA-GEIGY AG

granules

The following substances are used to produce 57o granules:

5 parts of active ingredient of formula I.

0.25 part of epichlorohydrin

0.25 part of cetyl polyglycol ether

3.50 parts of polyethylene glycol

91 parts of kaolin (grain size 0.3-0.8 mm)

The active substance is mixed with epichlorohydrin and dissolved in 6 parts of acetone, then polyethylene glycol and cetyl polyglycol ether added. The solution obtained in this way is sprayed onto kaolin and then evaporated in a vacuum.

Wettable powder

To produce a) 50%, b) 25% and c) 10% The following ingredients are used:

a) 50 parts of active ingredient of formula / I, e.g. 2,3-dimethyl

N- (I ¹ -methoxyprop-2 ¹ -yl) -N-chloroacetaniiide

5 parts of sodium dibutyl naphthyl sulfonate

3 parts of naphthalenesulfonic acids-phenolsulfonic acids-formaldehyde condensate 3: 2: 1,

20 parts of kaolin, 22 parts of Clisspagne chalk;

i 0 9 8 3 2 / "J I 2 8

CISA-GSGY AG

b) 25 parts of active ingredient of the formula I.

5 parts of oleyl methyl tauride sodium salt,

2.5 parts of naphthalenesulfonic acid formaldehyde -Condensate,

0.5 parts of carboxymethyl cellulose,

5 parts neutral potassium aluminum silicate,

62 parts of kaolin;

c) 10 parts of active ingredient of the formula I,

3 parts mixture of the sodium salts of

saturated fatty alcohol sulfates,

5 parts of naphthalenesulfonic acid formaldehyde

hyd condensate,

82 parts of kaolin.

The specified active ingredient is appropriate on cfie Carriers (kaolin and chalk) drawn up and then mixed and ground. You get Wettable powder with excellent wettability and suspension properties. Such wettable powders can be diluted by diluting them with water suspensions of any desired concentration can be obtained.

paste

The following substances are used to produce a 45% paste:

409832/1128

CIBA-GEIGY AG

- 50 parts of active ingredient of formula I 5 parts of sodium aluminum silicate, 14 parts of cetyl polyglycol ether with 8 mol

Ethylene oxide,

1 part oleyl polyglycol ether with 5 mol

Ethylene oxide,

2 parts spindle oil,

10 parts of polyethylene glycol, - 18 parts of water.

The active ingredient is intimately mixed and ground with the additives in suitable equipment. Man receives a paste which, by dilution with water, can be diluted with suspensions of any desired concentration can be produced.

Emulsion concentrate

For the production of a 20-307o emulsion concentrate

20-30 parts of active ingredient of formula I.

5 parts of a mixture of nonylphenol polyoxyethylene and calcium dodecylbenzenesulfonate,

35 parts of 3,5,5-trimethyl-2-cyclohexen-1-one, 40-30 parts of dimethylformamide

409832/1128

CLBA-GEIGY AG

mixed together .. This concentrate can be diluted to suitable concentrations with water to form emulsions will. Such emulsions are suitable for controlling weeds in crops.

409832/1 128

Claims (1)

Claims R is an alkyl radical with a maximum of 3 carbon atoms, an alkenyl radical with 3 or 4 carbon atoms, a cyclopropyl radical or a cyclopropylmethyl radical, A is an unsubstituted ethylene chain or a Ethylene chain monosubstituted by ethyl or mono- or disubstituted by methyl, R, hydrogen or an alkyl radical with a maximum of 4 carbon atoms. R _{0 is} an alkyl radical with a maximum of 4 carbon atoms, Ro and R, independently of one another, one each for the amino group meta-position substituents, namely halogen ·, cyano, alkyl, alkylthio- 'or alkoxy each with a maximum of 3 carbon atoms, haloalkyl with 1 or 2 carbon atoms and 1 up to 3 halogen atoms, alkoxyalkyl or alkylthioalkyl with 2 to 4 carbon atoms, and one of the substituents R 1 or R, also hydrogen, and 40 9832/1126 CIBA-GEIGYAG X chlorine or bromine mean, together with suitable carriers and / or distribution agents. 2. Agent according to claim 1, wherein X is chlorine. 3. Agent according to claim 2, wherein R 1 and R "each have one Denote an alkyl radical whose total carbon number does not exceed 5. 4. Agent according to claim 1, in which A, R, R ,, R ₂ and X have the meaning mentioned and in which one of the substituents R ~ or R, which is in the position meta to the amino group, is chlorine, the cyano, trifluoromethyl, methoxy or methylthio group and the other substituent is hydrogen. 5. Agent according to claim 4, wherein A is an ethylene chain monosubstituted by methyl or ethyl means. 6. Agent according to claim 1, wherein A and R have the meanings mentioned, X is chlorine, R is a methyl group R “represents hydrogen, methyl or ethyl means in which the substituent R ~ in the position meta to the amino group is an alkyl radical with a maximum of 3 Carbon atoms and R, is hydrogen. 7. Means according to claim 1, which contain a compound of the formula Ia 409832/1 1 28 CIBA-GEIGY AG (Ia) wherein R ' _{2 is} hydrogen, a methyl or ethyl group and R' and R ₁ . are independently a methyl or ethyl group. 3. Agent according to claim 1, containing 2,3-dimethyl-N- (I ¹ -methoxyprop-2 ¹ -yl) -N-chloroacetanilide of the formula CH ₃ -CH ₂ -O-CH ₃ O-CH Cl 9. Agent according to claim 1, containing 2,3-dirnethy1-6-ethyl-N- (l'-methoxyprop-2 ¹ -yl) -N-chloroacetanilide. 10. A composition according to claim 1, containing 2,6-dimethyl-3-chloro-N- (2'-methoxyethyl) -N-chloroacetanilide. 11. Means according to claim 1 ,. containing 2,6-dimethyl-3-methoxy-N- (2'-methoxyethyl) -N-chloroacetanilide. 12. Agent according to claim 1, containing 2,6-dimethyl-3 · methoxy-N- (1'-methoxyprop-2'-yl) -N-chloroacetanilide. AC9832 / 1 128 CIBA-GEIGY AG 13. Agent according to claim 1, containing 2,6-dimethyl-3-trifluoromethyl-N- (2'-methoxyethyl) -N-chloroacetanilide. 14. Agent according to claim 1, containing 2,6-dimethyl-3-trifluoromethyl-N- (l'-methoxyprop-2 ¹ -yl) -N-chloroacetanilide. 15. Process for the preparation of compounds of the formula I. A-OR (D CO-CH ₂ X R is an alkyl radical with a maximum of 3 carbon atoms, an alkenyl radical with 3 or 4 carbon atoms, a cyclopropyl radical or a cyclopropylmethyl radical, A is an unsubstituted ethylene chain or one with ethyl or one with methyl or doubly substituted ethylene chain, R _{1 is} hydrogen or an alkyl radical with a maximum of 4 carbon atoms. R "is an alkyl radical with a maximum of 4 carbon atoms, R "and R, independently of one another, each one to the amino group meta-position substituents, namely Halogen, cyano, alkyl, alkylthio or alkoxy with a maximum of 3 carbon atoms each, haloalkyl with 1 or 2 carbon atoms and 1 4C9832 / 1 128 CIBA-GEIGY AG up to 3 halogen atoms, alkoxyalkyl or alkylthioalkyl with 2 to 4 carbon atoms, and one of the substituents R "or R, too Hydrogen, and X is chlorine or bromine, characterized in that an N-substituted aniline of the formula II wherein R, R ,, R ~, R ,, R / and A the indicated Have meaning, reacts with a halogen acetylating agent. 16. The method according to claim 15, characterized in that that the anhydride or halide of chloroacetic acid or bromoacetic acid is used as the halogen acetylating agent used. 17. Methods for selective weed control in crops of useful plants, characterized by the use of compounds according to claim 1. 18. The method according to claim 17, characterized by the use of compounds according to one of the Claims 2 to 14. 19. Compounds of the formula I according to claim 1. 20. Compounds according to one of claims 2 to 14 « U9832 / 1128