DD153566A5 - HERBICIDE MEDIUM - Google Patents

Abstract

1. A substituted urea of the formula I see diagramm : EP0027965,P26,F1 where R**1 denotes substituted phenyl of one of the formulae see diagramm : EP0027965,P26,F2 see diagramm : EP0027965,P26,F3 or see diagramm : EP0027965,P26,F4 R', R" and R'" being identical or different and each denoting hydrogen, halogen, nitro, lower alkyl, halo-lower alkyl, cyano, lower alkoxy, halo-lower alkoxy, lower alkylmercapto, lower alkylsulfinyl or lower alkylsulfonyl, or R**1 denotes substituted or unsubstituted heteroaryl, R**2 denotes hydrogen, lower alkyl, lower alkoxy, lower alkenyl, lower alkynyl or cycloalkyl, R**3 denotes hydrogen or lower alkyl, R**2 and R**3 together also being able to denote oligomethylene or oxaoligomethylene, and X denotes hydrogen, halogen, nitro, lower alkyl, halo-lower alkyl, lower alkoxy, halo-lower alkoxy, or cyano, but does not denote nitro if R**2 and/or R**3 are lower alkyl.

Description

5 The new herbicides can be used in agriculture to control undesired plant growth.

Characteristic of the known technical solutions

It is already known that the herbicidally active substance N, N-dimethyl-N '[4- (4-chlorophenoxy) -phenyl! -Urea has a good compatibility with carrots (Daucus carota) and beans (Phaseolus vulgaris) (DE -AS 11 42 25D · However, so far it is only limited in soybeans

15 (Glycine max), strawberries (Pragaria vesca) and in some onions (Allium сера) or in celery (Apium graveolens) applied (Herbicide Handbook of the Weed Science Society of America, 4th Ed., 1979). However, this herbicide has the disadvantage that it can be used as a post-treatment.

Running agent must be applied very early and only at very young stages of development of the weeds satisfactorily acts. In addition, its phytotoxicity for soybeans and onions may become more severe and critical.

Other substituted 4-Phenoxyphenylharnstoffe with selewe tive herbicidal properties have been described in DE-OS 19 01 501. German Offenlegungsschrift 2,411,320 also discloses herbicidally active (trifluoromethylphenoxy) phenylureas.

wrote, but which are only compatible with carrots. Finally, the aus, Ν-dimethyl-N ¹ [4- (3-trifluoromethylphenoxy) phenyl] urea known from the example of action of DE-OS 25 38 178 and preferably used postemergence leaves no selectivity any more recognizable.

Object of the invention

The aim of the invention is the development of herbicidal agents with improved activity against undesired plant growth.

Explanation of the essence of the invention

The invention has for its object to provide new chemical compounds with herbicidal activity.

It has been found that substituted ureas of the formula I

R ^X -CK 0 R ²

// \ -NH-C-N I,

⁴ ^ ^ R ³

X

wherein R is either a substituted phenyl radical of

or-20

R "'R" ¹

in which R ', R "and R"' are each independently of one another hydrogen, halogen, nitro, lower alkyl, halogeno-lower alkyl, cyano, lower alkoxy, halo-lower alkoxy, lower alkylmercapto, lower alkylsulfinyl or lower alkylsulfonyl or represents an optionally substituted heteroaryl radical,

R ^{2 is} hydrogen, lower alkyl, lower alkoxy, lower alkenyl, lower alkynyl, cycloalkyl or optionally substituted phenyl,

3 2

R is hydrogen or lower alkyl, wherein R and R- ^{5 may} together also stand for oligomethylene or oxaoligomethylene, and

X is hydrogen, halogen, nitro, lower alkyl, halo-lower alkyl, lower alkoxy > halo-lower alkoxy or cyano

_ о

compared to 4-phenoxy-substituted phenylureas in addition to a considerable herbicidal activity still have a surprisingly good compatibility with a number of crop plants.

If R is a substituted phenyl radical, then R ', R "and R'" may each independently of one another denote: hydrogen, fluorine, chlorine, bromine, iodine, nitro, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, fluoromethyl, trichloro

Ю methyl, dichloromethyl, chloromethyl. Difluoromethyl, 1-chloroethyl, 2-chloroethyl, 1-fluoroethyl, '2-fluoroethyl, 2,2,2-trichloroethyl, 2,2,2-trifluoroethyl, 1,1,2,2-tetrafluoroethyl, l, l, 2 Trifluoro-2-chloroethyl, 1,1,2,2,2-pentafluoroethyl, methoxy, ethoxy, trichloromethoxy, trifluoromethoxy, 1-chloroethoxy, 2-chloroethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2,2,2-trichloroethoxy , 2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 1,1,2,2,2-fentafluoroethoxy, methylmercapto, ethylmercapto, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl. Among these radicals, fluorine, chlorine, trifluoromethyl and trifluoromethoxy are preferred.

As heteroaryl radicals, the following are preferred for R:

25 _

N-N N-N

R may be hydrogen, methyl, ethyl, propyl, isopropyl, tert-butyl, methoxy, ethoxy, vinyl, propen-1-yl, allyl, crotyl, methallyl, buten-1-yl-3, butene-1, yl-4, ethynyl, propyn-1-yl, propargyl, butyn-2-yl-1, butyn-1-yl-3-butyn-1-yl-4, 3-methylbutyn-1-yl-3 , Cyclopropane, cyclobutane, cyclopentane, cyclohexane, 2-methylcyclohexane, 3,4-dichlorophenyl or 3-trifluoromethylphenyl. Preferred are methyl and ethyl.

R may be hydrogen and preferably methyl or ethyl. If R and R ^{J are} a cycloalkyl radical, R and R ^J together with the nitrogen may denote pyrrolidine, 2,5-dimethylpyrrolidone or piperidine.

X can be: hydrogen, fluorine, chlorine, nitro, methyl, ethyl, trichloromethyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, trifluoromethoxy, trichloromethoxy or cyano. Preference is given to hydrogen and nitro.

Furthermore, it has been found that the substituted phenylureas of the formula I are obtained if

a) substituted anilines of the formula II

NH ₂ II,

R ³ ^ -O

in which R and X have the abovementioned meanings, with phosgene and then with amines of the formula III

R ²

H-N III,

2 Я

in which R and R have the abovementioned meanings,

b) substituted anilines of the formula II with a carbohydrate

amic acid chloride of formula IV

0 R ² Cl-CN IV,

⁴ R ³

2 3

in which R and R have the abovementioned meanings,

c) substituted anilines of the formula II with alkyl isocyanates of the formula V

R ³ -N = C = OV,

in which has the abovementioned meaning except hydrogen, or

d) 3-substituted benzoyl halides of the formula VI 10

R ^1- -O ч 0

VI,

in which R and X are the above meanings

have, reacted with an alkali azide or trimethylsilyl azide and converted the thus obtained acid azides into the corresponding isocyanates and the latter is reacted with amines of the formula III.

All four preparation processes a), b), c) and d) are preferably carried out with the concomitant use of suitable solvents or diluents. As such, virtually all inert organic solvents come into question. These include in particular: hydrocarbons such as ligroin, gasoline, toluene, pentane, hexane, cyclohexane, petroleum ether, halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, 1,1- and 1,2-dichloro

30 ethane, 1,1,1- and 1,1,2-trichloroethane, chlorobenzene,

o, m, p-dichlorobenzene, o, m, p-chlorotoluene, nitrohydrocarbons such as nitrobenzene, nitroethane, o, m, p, nitrotoluene, nitriles such as acetonitrile, butyronitrile, isobutyronitrile, ethers such as diethyl ether, di-n propyl ether, tetra-

hydrofuran, dioxane, esters such as acetoacetic ester, ethyl acetate, isobutyl acetate, furthermore ketones such as acetone, methylethyl, methylisopropyl and methyl isobutyl ketone, as well as amides such as methylformamide and dimethylformamide.

The process a) can be carried out very well by first reacting the substituted aniline of the formula I with an excess of phosgene in the corresponding isocyanate (see Houben-Weyl, Volume 8, 1952, page 122 to 123 or Methodicum Chimicum, Volume 6, 197 ¹ *, page 780) and then with at least the equivalent amount of amine of formula III optionally in the presence of a solvent at a temperature of -10 ⁰ C to 150 ⁰ C, preferably from 20 ⁰ C to 120 ⁰ C, continuously or

15 discontinuously reacted.

According to b), the substituted aniline of the formula II according to a general method of Houben-Weyl, Volume 8, 1952, pages 160 to 161 with an excess of up to

20 20 % NjN-Dialkylcarbamidsäurechlorid the formula IV optionally in the presence of a solvent and optionally in the presence of an acid binder at a temperature of -10 ° to 150 ⁰ C, preferably from 20 ° to 120 C, reacted continuously or discontinuously.

As acid binder, all customary acid binders can be used. These preferably include alkali metal hydroxides, alkali metal carbonates, alkali metal and tertiary organic bases. Specific examples which may be mentioned are sodium hydroxide, sodium bicarbonate, sodium methylate, triethylamine, pyridine, trimethylamine, o6, β, 7-picoline, lutidine, Ν, Ν-dimethylaniline, Ν, Ν-dimethylcyclohexylamine, quinoline, triethylamine. n-propylamine, tri-n-butylamine and acridine.

In the process с) is the substituted aniline of the formula II with an excess of up to 20 % isocyanate of formula V, optionally in the presence of a solvent at a temperature of -10 ° to 150 ° C, preferably ^v 20 ° to 12O ⁰ C, reacted continuously or discontinuously (see Houben-Weyl, Volume 8, 1952, pages 157 to 159).

For carrying out process d), 0.1 mol of benzoyl chloride is initially mixed with 0.1 to 0.4 mol of alkali metal azide or trisodium chloride.

methylsilylazide reacted in excess to the corresponding phenyl isocyanate. This is optionally by concentration of the reaction mixture as. Isolated crude product and admixed for further reactions, optionally in the presence of a solvent with the at least equimolar amount of amine. The process works particularly well when the benzoic acid chloride of the formula VI is reacted with trimethylsilyl azide, then thermally treated according to a protocol of H.R. Kricheldorf in Synthesis 1972, pages 551 to 553 converted into the entsprechnede isocyanate and then with

20 an amine of formula III, optionally in the presence

of a solvent at a temperature of -10 ⁰ C to 15O ⁰ C, preferably from 20 ⁰ C to 120 ⁰ C, continuously or discontinuously.

The isolation of the end products is carried out either by precipitation from the reaction mixture by suction and subsequent purification by recrystallization or chromatography or by concentration of the reaction mixture in vacuo to dryness and purification of the reaction mixture.

30 Standes by recrystallization or chromatography.

The as starting materials for the reactions a),. b), c) usable substituted anilines of the formula III are in part new. They can be prepared by common methods described in the literature.

The 3-substituted benzoic acid chlorides of the formula VI required as starting materials for d) can likewise be prepared from their known carboxylic acids (US Pat. Nos. 4,031,131 and 6,252,645) or by the methods described there with the aid of chlorinating agents.

embodiment

Preparation of starting materials:

a) 63.6 parts of 3-2'-chloro-trifluoromethylphenoxy-l-nitro-benzene are dissolved in 200 ml of ethanol, treated with 10 g of Raney nickel as a catalyst and hydrogenated at 50 ° C and 100 atm of hydrogen. After removal of the catalyst, the solvent is removed in vacuo, the residue taken up in ether, the amine is precipitated by gassing with hydrochloric acid and isolated. By treatment with dilute sodium hydroxide solution, the amine can be released. This gives 42.4 parts (75 % of theory) of 3-2'-chloro-4'-trifluoromethylphenoxyaniline with n: ⁵ : 1.5542.

b) 34.6 parts of 3,6-dichloropyridazine in 100 parts of dimethyl sulfoxide are added in portions at 40 ^° C. to a suspension of 35 * 2 parts of dipotassium salt of 3-hydroxybenzoic acid in 100 parts of dimethyl sulfoxide.

25 is then stirred for 5 hours at 9O ⁰ C,

Cools, the entire reaction mixture is stirred into 1000 parts of water and acidified with concentrated hydrochloric acid. The precipitate is filtered off with suction and, after drying, 45 parts (= 90 % of theory) of 3-6'-chloropyridazinyl-3'-oxybenzoic acid are obtained with the enamel

point 187 - 192 ° C.

c) 26.7 parts of 3-6'-chloropyridazinyl-3'-oxybenzoyl chloride are dissolved in 100 parts of absolute dioxane and treated with 13.8 parts of trimethylsilyl azide. You warm up

3 hours at 9O ⁰ C, cooled, concentrated, the Re'aktionsgemisch under vacuum and receives 24 parts (= 100 % of theory) 3-6'-Сп1огругіаагіпу1-3'-охурпепу1ізо-cyanate with a melting point of 90 95 ° C. (Zers ..) and a purity of about 90 %.

The phenyl isocyanates obtained by this method can be used without further purification for the preparation of urea derivatives.

Production of final products:

example 1

14.4 parts of 3-2 '-chloro-4 * -trifluoro methyl phenoxyanilin be dissolved in 50 parts of acetonitrile and treated at 20 ⁰ C with 3 drops of triethylamine and 3.2 parts of methyl isocyanate. The mixture is stirred for 2 hours at room temperature, the reaction mixture is concentrated to dryness and the residue is recrystallized from toluene. This gives 10 parts (= 58 % of theory) of N-methyl-N'-3- (2'-chloro-4'-trifluoromethylphenoxy) -phenylurea with the melting point 158 - l6l ° C.

Example 2

To a solution of 14.4 parts of 3-2'-chloro-4'-trifluoro-

Methylphenoxyaniline in 25 parts of pyridine is added at 1O ⁰ C 7.5 parts of Ν, Ν-dimethylcarbamoyl chloride in portions to. It is heated for half an hour at 70 to 75 ° C, the pyridine removed for the most part in vacuo, the residue poured onto water and acidified with dilute hydrochloric acid. The oily residue is taken up in methylene chloride, dried with magnesium sulfate and concentrated. After chromatography on silica gel with

35 toluene / Асеton 70: 30 eluent gives 14 parts

- 10 -

" ^r (= 78 % of theory) Ы, Ы

fluoromethylphenoxy) -phenylurea with the melting point 96-98 ⁰ C.

5 Example 3

12.4 parts of S-ß'-chloropyridazinyl-S'-oxyphenylisocyanat are dissolved in 150 ml of acetonitrile and treated at 2O ⁰ C with 3 drops of triethylamine and 3.1 parts of N-methyl-O-methylhydroxylamine. It is stirred for 1 hour at room temperature, the reaction mixture is concentrated under vacuum and the residue is recrystallized from a little acetonitrile. This gives 12 parts (= 79 % of theory) of N-methyl-N-methoxy-N'-3- (6'-chloropyridazinyl-3'-oxy) -phenylurea with a melt

15 point from 111 - 113 ° C.

Analogously to Example 1-3, the compounds indicated in the following overview were prepared:

"Example No. R, ¹

4 5

б 7 8

Cl

Rf

X pp; η.

, .25 D

с ₂ н ₅ C ₂ H ₅ H 1.5412 CHCH, C = CH CH H 112-118 ⁰ C -OCH CH, H 1.5501

-CH ₃ C ₃ H ₇ (DH 132-134 ° C

10 11

12 13

CH ₃ CH ₃ NO ₂ 133-135 С C ₂ H ₅ C ₂ H ₅ It 118-123 ° C сн-сн "I ί C = CH CH ti 8О-85 ° С

58-62 ⁰ C

Example No. R ^J ; η * ⁵

15

16 17 18 19

20 21 22

23 24 25

26 27

Cl

vci

CP, C = CH

снсн_

I J

C = CH

C ₂ H ₅

C ₂ H ₅

CH,

CH,

C ₂ H ₅

NO,

Il сн ₃ H 1.5524 C ₂ H ₅ C ₂ H ₅ H 1.5392 CH ₃ H H 1.5502 -снсн_ CH- H 1.5498

NO,

NO,

H 1,5601

^C 2 ^H 5 H 1.5513 H H 1.5637 OFL H 1.5569

NO,

NO,

Example No. R

fp; n

28 29 30

31 32

33 34 35

Cl

CH

C ₂ H ₅

CH ₃

C ₂ H ₅

CHCH ₀ C = CH

CH.

CH, CH ₃

C ₂ H ₅

N0,

1.5920

164-166 ⁰ C

c = o ^{= l65} °

135-139 C

N0,

36 37 38

39 40

-CH ₃

-CHCH ₀ C = CH

CE.

CH,

N0,

63-68 ° C

1.5492

Belspiel No. R ^J R-

42

44

45

46 47 48

49 50

Cl

f VCP,

c /

CF

N0,

OCH ^

O ₂ H ₅

^{: н} з

c ₂ h ₅

N0.

сн ₃ Il π 161-165 "C Il H Il 176-180 ⁰ C C ₂ H ₅ O ₂ H ₅ Il U ₃ -HT ⁰ C -snnn_ I J C = CH сн ₃ Il 164-165 ° C

N0,

121-125 ° C

Example No. FT

X pp; η * ⁵

51

Cl

CH CH

5253

Cl

-ГУ ⁰¹

63-66 ° c

Cl

54 / / Vocp CH ₃ CH 55 ti C ₂ H ₅ ^C 2 56 CH ₃ H 57 11 -CHCH, t 5 C = CH CH 58 It CH ti

NO,

59

Cl

Cl

Cl

Example No. R ^J

60

61 62

63

64

65

66

67

Cl

CP C

= 3

Cl

Cl

Cl Cl

Cl

CF CF,

Cl CH,

^5H 3

NO,

C ₂ H ₅ O ₂ H ₅ H CH ₃ OCH, H CF ti N0

Example No. R ^J

R-

68

Cl

Cl 'Cl CH

^ш з

69

70

CN

Cl

71 72

• 73

CN "

н ₃ о

NO,

74 75

76

CH ₂ -CH (CH) ₂ H 1.5423

f ^H 3

-CH-C ₂ H ₅

119-123 с

C ₃ H ₇ (I) C ₃ H ₇ (J.) "118-122 ⁰ C

Example No. R

R-

X pp; n

77

/ Л-СР,

H _co = 1670 cm

Cl

787980

N0,

CH.

CH

1.5619

" _CO = 1650 cm

C O

1640 cm '

81

"со ^{= 1б2 {0 cm}

Il.

N ' CO

= 1640 cm

83

N0,

Cl

HC CH

1.5895

8485

N = N ⁷

H OyO γ'-CH- "

Cl H

CH,

-CH-C ₂ H ₅

136-138 ⁰ C

180-182 ⁰ C

Example No. R ¹ R ² R ³ X Pp; η ²

C ₃ H ₇ Ci) ^ C ₃ H ₇ (I) H 159-162 ° C

CH - / ^ "195-198 ° '

OCH - / н \ "148-152

N0 148-150 ⁰ C

5 86 87 88 Ю 89

HC CH

90 "0 H 194-19 ° C

£ 91> CP ₃ H / = \ 159 ° C

(Decomposition)

The new active ingredients have in particular a strong herbicidal activity and a good compatibility with crop plants. Furthermore, they have a fungicidal activity.

Their application is e.g. in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, scattering agents, granules by spraying, misting, dusting, scattering or pouring. The forms of application depend entirely on the intended use.

For the preparation of directly sprayable solutions, emulsions, pastes and oil dispersions come mineral oil fractions from medium to: high boiling point, such as kerosene

or diesel oil, coal tar oils, etc., and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Benzene, toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives e.g. Methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, cyclohexanol, cyclohexanone, chlorobenzene, isophorone, strong polar solvents, e.g. Dimethylformamide, Dime thylsulf oxide, N-methylpyrrolidone and water into consideration.

Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (spray powders), oil dispersions by addition of water. For the preparation of emulsions, pastes or oil dispersions, the substances can be dissolved as such or in an oil or solvent, including wetting, adhesive , Dispersing or emulsifying agents are homogenized in water. However, it is also possible to prepare from active substance, wetting, adhesion, dispersing or emulsifying agent and possibly solvent or oil.

20 concentrates are prepared, which are suitable for dilution with water.

Surfactants include:

Alkali, alkaline earth, ammonium salts of lignosulfonic acid, naphthalenesulfonic acids, phenolsulfonic acids, alkylarylsulfonates, alkylsulfates, alkylsulfonates, alkali and alkaline earth salts of dibutylnaphthalenesulfonic acid, lauryl ether sulfate, fatty alcohol sulfates, fatty alkali and alkaline earth salts, salts of sulfated hexadecanols, heptadecanols, octadecano-Ie, salts of sulfated Pettalkoholglykolether, condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenolether, ethoxylier-

35 t isooctylphenol, octylphenol, nonylphenol, alkyl

phenol polyglycol ethers, tributylphenyl polyglycol ethers, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignin, liquors and methyl cellulose.

Powders, scattering and dusting agents can be prepared by mixing or co-grinding the active substances with a solid carrier.

Granules, e.g. Coated, impregnated and homogeneous granules can be prepared by binding the active compounds to solid carriers. Solid carriers are e.g. Mineral earths such as silica gel, silicic acids, silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, talc, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide and ground plastics.

Examples of formulations are:

I 20 parts by weight of the compound of Example 1 are dissolved in 3 parts by weight of the sodium salt of diisobutylnaphthalenesulfonic acid, 17 parts by weight of the sodium

25 triumsalzes a lignosulfonic acid from a sulfite liquor and 60 parts by weight of powdered silica gel well mixed and ground in a hammer mill. By finely distributing the mixture in 20,000 parts by weight of water, an injection molding

broth containing 0.1% by weight of the active substance.

II 3 parts by weight of the compound of Example 2 are intimately mixed with 97 parts by weight of finely divided kaolin. This gives a dust,

containing 3 wt. $ of the active ingredient.

III 30 parts by weight of the compound of Example 3 are intimately mixed with a mixture 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. This gives a preparation of the active substance with good adhesion.

IV 40 parts by weight of the compound of Example 4

Inn the intimately mixed with 10 parts of sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate, 2 parts of silica gel and 48 parts of water. A stable aqueous dispersion is obtained. By diluting with 100 000 parts by weight of water to obtain an aqueous

Dispersion containing 0.04 wt.% Of active ingredient.

V 20 parts of the compound of Example 5 are mixed with 2 parts of calcium salt of dodecylbenzenesulfonic acid,

8 parts of fatty alcohol polyglycol ether, 2 parts Natriurasalz a phenolsulfonic acid-urea-fоrmaldehyd- condensate and 68 parts of a paraffinic mineral oil intimately mixed. This gives a stable oily dispersion.

25 VI Mix 90 parts by weight of the compound of

Example 1 with 10 parts by weight of N-methyl - ^ - pyrrolidone and obtains a solution which is suitable for use in the form of very small drops.

VII 20 parts by weight of the compound of Example 2 are dissolved in a mixture consisting of 80 parts by weight of xylene, 10 parts by weight of the adduct of 8 to 10 moles of ethylene oxide with 1 mole of oleic acid N-monoethanolamide, 5 parts by weight of calcium salt of dodecyl

35 benzenesulfonic acid and 5 parts by weight of the plant

product of 40 moles of ethylene oxide to 1 mole of castor oil. By pouring and finely distributing the solution in 100,000 parts by weight of water to obtain an aqueous dispersion containing 0.02 wt.% Of the active ingredient.

VIII 20 parts by weight of the compound of Example 3 are dissolved in a mixture consisting of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutylene

butanol, 20 parts by weight of the adduct of 7 moles of ethylene oxide to 1 mole of isooctylphenol and 10 parts by weight of the adduct of 40 moles of ethylene oxide to 1 mole of castor oil. By pouring and finely distributing the solution

15 in 100 000 parts by weight of water are obtained. an aqueous dispersion containing 0.02% by weight of the active ingredient.

IX 20 parts by weight of the compound of Example 3

are dissolved in a mixture consisting of 25 weight steep cyclohexanol, 65 parts by weight of a mineral oil fraction of boiling point 210 to 28O ⁰ C and 10 parts by weight of the adduct of 40 moles of ethylene oxide to 1 mole of castor oil. By pouring and finely distributing the solution in 100,000 parts by weight of water to obtain an aqueous dispersion containing 0.02 wt. % Of the active ingredient.

Examples of herbicidal activity

The influence of various representatives of the compounds according to the invention on the growth of unwanted and of crop plants is demonstrated in subsequent greenhouse experiments.

The culture containers used were plastic flower pots of 300 cnr content and loamy sand with about 1.5 % humus as substrate. The seeds of the test plants according to Table 1 were sown flat separately by species. Immediately thereafter, application of the active ingredient to the surface of the earth took place in the preliminary application. It was suspended or emulsified in water as a distribution agent and sprayed by means of finely distributing nozzles. After application of the agents, the vessels were lightly rained to stimulate germination and growth while also activating the chemical agent. Thereafter, the containers were covered with transparent plastic hoods until the plants had grown. This cover caused a uniform germination of the test plants, if that

15 was not affected by the chemicals.

Table 1 - List of plant names

Botanical name

German name

Amaranthus retroflexus Cassia spp.

Centaurea cyanus Chenopodium album Chrysanthemum segetum Cyperus ferax Echinochloa crus galli Euphorbia geniculata Glycine max Gossypium hirsutum Hordeum vulgaris Lamium spp.

Matricaria spp.

Sesbania exaltata Sinapis alba Solanum nigrum Sorghum bicolor Triticum aestivum Zea mays

Chenopodium spp.

Curved Foxtail Cassia species Cornflower White Goosefoot

Chicken millet South America. Wolf's Meal Chart Soybeans Cotton Barley

Deadnettle species Camomile species Turibaum White mustard Black nightshade Sorghum (millet) Wheat

Corn

Gänsefußart

For the purpose of Nachlaufbehändlung pulled the plants depending on the growth form in the test tubes only to a height of 3 to 10 cm and then treated. A cover was omitted. The setup of the experiments was carried out in a greenhouse, hotter for hotter species (25 to 40 ⁰ C) and for those temperate climates 15 to 30 C were preferred. The trial period lasted for 3 to 6 weeks. During this time, the plants were maintained and their response to each treatment was evaluated. The following

Tables contain the test substances, the respective dosages in kg / ha of active substance (a.S.) and the test plant species.

5 is scored on a scale of 0 to 100.

0 means no damage or normal spillage and 100 no emergence of the plants or complete destruction of at least the above-ground sprouts. 10

ся

Table 2 - Control of unwanted broadleaf plants in cotton postemergence in greenhouse

Test plants active ingredients and damage %

Example No. 18 Example No. 0.25 kg / ha a.S. 0.25 kg / ha a.S. Comparative agent (N, N-dimethyl-N '- [H-chloro-phenoxy) -phenyl] -harnate 1.0 kg / ha a.s.

Gossypium hirsutum 10 Amaranthus retroflexus 100 Euphorbia geniculata 95 Sesbanla exaltata 80

10

100

95 62 48 32 35

0 = no damage 100 = plants died

й 8 ^ о öi S

Table 3 - Selective removal of broadleaf weeds in soy and corn in post-emergence application in the greenhouse

Test plants active ingredients and damage % at 1.0 kg / ha aS

Example No. 2 Comparative agent

(N, N-dimethyl-N '- [4-chlorophenoxy) -phenyl] -urea

Glycine max 15 32

Zea mays 13 10

Cassia spp. 100 0

Chenopodium spp. 99 52

Sesbanja exaltata 80 35

Slnapls alba 90 99

0 = no damage 100 = plants died

К)

Ν "

cn

ul

Table 4 - Selective removal of unwanted * crops in cereals postemergence in the greenhouse

test plants

Active substances, application rate and damage % Example No. 6 Example No. 46 Example No. 12 0.5 kg / ha aS 0.25 kg / ha aS 1.0 kg / ha

Hordeum vulgar 0

Triticum aestivum 0

Aihäranthus retroflexus -

Chenopodium album 98

Lamium spp. 80

0 = no damage 100 = plants died

<*> C »> ¹ ^ * ^м гй?>

Ol О ІЯ О ІЯ О у,

Table 5 - Selective removal of undesirable plants in different crops in pre-emergence application in the greenhouse

Active ingredient of Example No. 47

Test plants injury % at 1.0 kg / ha aS

Hordeurn vulgar 0

Glycine max 9

Gossypium hirsutum 10

U)

Sorghum bicolor 3

Zea mays O

Amaranthus retroflexus 99

Chrysanthemum segetum 100

Centaurea cyanus 80

Cyperus ferax 100

Echinochloa crus galli 82

Matricarla spp. 95

Solanum nigrum 100

0 = no damage, 100 = plants died

Table б - Example of the herbicidal action of various new compounds in pre-emergence application in the greenhouse

5 active ingredient of the test plants and injury %

Example No. at 3.0 kg / ha a.S.

Slnapis alba

3 100-

100 4 100

11 100

12 100

16 100

17 100 18 100

22 100

45 100

46 100 48 100

53 100

Tables 2-6 present the selective herbicidal activity of the compounds of the invention. The application can be carried out pre-emergence or with better success in post-emergence applications. The mortars can be applied to the site before the unwanted plants have germinated from the seeds or expelled from vegetative plant parts or they are applied to the leaves of the unwanted plants and crops. Another application technique is that the active ingredients are sprayed with the help of sprayers so • that the leaves of sensitive crops are not hit if possible, while the active ingredients on the underlying soil or growing there unwanted plants reach (post-direc-

15 ted, lay-by).

Depending on the season and the stage of growth, the application rates are from 0.1 to 15 kg / ha and more, preferably from 0.2 to 3 kg / ha, the higher doses being suitable for the total control of plant growth.

In view of the versatility of the application methods, the compositions according to the invention or mixtures containing them can be used, in addition to the crop plants listed in the tables, in a further large number of crops to eliminate undesired plant growth.

Specifically, the following crops may be mentioned: 30

Botanical name German name

Allium сера Ananas comosus Arachis hypogaea Asparagus officinalls Avena sativa Beta vulgaris spp. altisslma Beta vulgaris spp. rapa Beta vulgaris spp. Brassica napus var. napus Brassica napus var. napobrassica Brassica napus var. rapa Brassica rapas var. silvestris Camellia slnensis Carthamus tinctorius Carya illinoinensis Citrus limon Citrus maxima Citrus reticulata Citrus sinensis

Coffea arabica (Coffea canephora Coffea liberica) Cucurais melo Cucumis sativus Cynodon dactylon Daucus carota Elaeis gulneensis Pragaria vesca Glycine max

Gossypium hirsutum (Gossypium arboreum

Gossypium herbaceum Gossypium vitifolium) Helianthus annuus Helianthus tuberosus Hevea brasiliensis

Onion pineapple

Peanut

Asparagus oats

Sugar beet Turnip Beet rape

Turnip Turnips Turnips

Tea shrub Safflower - safflower Thorny Pear Lemon Grapefruit Mandarin Orange, orange

coffee

melon

cucumber

Bermuda grass carrot

oil palm strawberry soybean

cotton

Sunflower Jerusalem artichoke Paracum tree

Botanical name German name

Hordeum vulgare Humulus lupulus Ipomoea batatas Juglans regia Lactuca sativa Lens culinaris Linum usitatissimum Lycopersicon lycopersicum Malus spp. Manihot esculenta Medicago sativa Mentha piperita Musa spp.

Nicotiana tabacum (N. rustica)

01ea europaea Oryza sativa Panicum miliaceum Phaseolus lunatus Phaseolus mungo Phaseolus vulgaris Pennisetum glaucum Petroselinum crispum

spp. tuberosum

Picea abies Abies alba Pinus spp. Pisum sativom Prunus avium Prunus domestica Prunus dulcis Prunus persica Pyrus communis Ribes sylvestre Barley Hops Sweet potatoes Walnut tree Lettuce Lentil Fiber-apple Tomato Apple Manioc Alfalfa Peppermint Fruit and plantain banana

tobacco

Olive tree rice

Panicle millet moon bean bean of the wild bean bush beans pearl or cattail millet root parsley

Red spruce fir Pine Garden peach Sweet cherry Plum Almond tree Peach Pear Red currant

Botanical name

German name

Ribes uva-crispa Ricinus communis Saccharum officinarum Seeale cereale Sesamum indicum Solanum tuberosum Sorghum bicolor Sorghum bicolor Sorghum dochna Spinacia oleracea Theobroma cacao Trifolium pratense Trlticum aestivum Vaccinium corymbosum Vaceinium vitis-idaea Vicia faba Vigna sinensis (V. unguiculata) Vitis vinifera Zea mays

Gooseberry castor

Sugar cane rye

sesame

Potato sorghum sugar millet spinach

Cocoa tree red clover

wheat

Cultivated Bilberry Cranberry Bean Beans Cow Bean Grapevine Corn

The new substituted ureas can be mixed together and applied together with numerous representatives of other herbicidal or growth-regulating active ingredient groups. Examples of suitable mixture components are diazines, N-phenyl-carbamates, thiocarbamates, diurethanes, halocarboxylic acids, phenoxy-fatty acids, triazines, amides, ureas, diphenyl ethers, triazone, uracils, benzofuran derivatives and others. Such combinations serve to widen the spectrum of action and sometimes achieve synergistic effects. A number of active ingredients which, together with the new compounds, give meaningful mixtures for a wide variety of applications are listed by way of example.

5-Amino-4-chloro-2-phenyl-3 (2H) -pyridazinone 5-Amino-4-bromo-2-phenyl-3 (2H) -pyridazinone 5-Amino-4-chloro-2-cyclohexyl-3 ( 2H) -pyridazinone 5-amino-4-bromo-2-cyclohexyl-3 (2H) -pyridazinone

5-Methylamino-4-chloro-2- (2-trifluoromethyl-phenyl) -3 (2H) -pyridazinone

5-methyl-4-amino сЫ.ог-2- (2- _е 4, _{о г,} ß, ß-tetrafluorethoxyphenyl- -3 (2H) -pyridazinone

10 5-Dimethylamino-4-chloro-2-phenyl-3 (2H) -pyridazinone 4,5-Dimethoxy-2-phenyl-3 (2H) -pyridazinone 4,5-Dimethoxy-2-cyclohexyl-3 (2H) - pyridazinone 4,5-dimethoxy-2- (2-trinomethylphenyl) -3 (2H) -pyrldazinone 5-methoxy-4-chloro-2- (2-trifluoro-ethyl-phenyl) -3 (2H) -pyrida-

Zinon

5-Amino-4-bromo-2- (2-methylphenyl) -3 (2H) -pyridazinone

3- (l-methylethyl) -lH-2, l, 3-benzothiadiazin-4 (3H) -one-2,2-

-dioxide and Salts 20 3- (1-Methylethyl) -8-chloro-1H-2,1,3-benzothiadiazine-4 (3H) -

-one-2,2-dioxide and salts

3- (l-methylethyl) -8-fluoro-lH-2, l, 3-benzothiadiazin-4 (3H) -

-one-2,2-dioxide and salts

3- (1-Methylethyl) -8-methyl-1H-2, 1,3-benzothiadiazine-4 (3H) -25 -one-2,2-dioxide and salts

1-Methoxymethyl-3- (1-methylethyl) -2,1,3-benzothiadiazine-4 (3H) -one-2,2-dioxide

1-Methoxymethyl-8-chloro-3- (1-methylethyl) -2,1,3-benzothia-30-diazin-4 (3H) -one-2,2-dioxide

1-methoxymethyl-8-fluoro-3- (1-methylethyl) -2,1,3-benzothiazine

dlazine-4 (3H) -one-2,2-dioxide 1-cyano-8-chloro-3- (1-methylethyl) -2,1,3-benzothiadiazine

-4 (3H) -one-2,2-dodioxide 35

1-cyano-8-fluoro-3- (1-methylethyl) -2,1,3-benzothiadiazine-4 (3H) -one-2,2-dioxide

1-cyano-1-methyl-S-Cl-methylethyl) -2,1,3-benzothiadiazine-4 (3H) -one-2,2-dioxide

5 l of cyano-3- (1-methylethyl) -2,1,3-benzothiadiazine-4 (3H) -one-2,2-dioxide

1-Azidomethyl-3- (1-methylethyl) -2,1,3-benzothiadiazinyl -4 (3H) -one-2,2-dioxide

3- (1-methylethyl) -1H- (pyridino [3,2-η] 2,1,3-thiadiazine - (4) -one-2,2-dioxide

N- (1-ethyl-propyl) -2,6-dinitro-3,4-dimethylaniline N- (1-methylethyl) -N-ethyl-2,6-din-tol-4-trifluoromethyl-aniline

N-n-propyl "N-.beta.-chloroethyl-2,6-dinitro-4-trifluoromethyl-aniline

N-n-propyl-N-cyclopropylmethyl ^ jo-dinitro - ^ - trifluoro-methyl-aniline N-Bls (n-propyl) -2,6-dinitro-3-amino-4-trifluoromethylaniline

N-bis (n-propyl) -2,6-dinitro-4-methylaniline N-bis (n-propyl) -2,6-dinitro-4-methylsulfonylaniline N-bis (n-propyl) -2 , 6-dinitro-4-aminosulfonyl-aniline Bis (β-chloroethyl) -2, ö-dinitro-A-methyl-aniline N-ethyl-N- (2-methylallyl) -2,6-dinitro-4-trifluoromethyl- -aniline

N -methyl-S ^ -dichlorbenzylester

N-Methylcarbamlnsäure-2,6-di (tert-butyl) -4-methylphenyl

esters

N-phenyl carbamic acid! s opr op yl ester N_3_pluorphenylcarbamic acid 3-methoxypropyl 2-ester isopropyl NS-chlorophenylcarbamate NS-chlorophenylcarbamic acid-butyn-1-yl-S-ester N-3-chlorophenylcarbamic acid 4-chloro-2-yl-l ester NS ^ -Dichlorphenylcarbaminsäure methyl ester

Methyl - (it-amino-benzenesulfonyD-carbamate) 0- (N-phenylcarbamoyl) -propanone oxime In N-ethyl-2- (phenylcarbamoyl) -oxypropionamide 3'-N-isopropyl-carbamoyloxy-propionanilide

Ethyl N- (3- (N'-phenylcarbamoyloxy; -phenyl) carbamate) Methyl N- (3- (N'-methyl-N'-phenyl-sarcamoyloxy) -phenyl) -carbamate isopropyl-N- (3- (3) N'-ethyl-N'-phenylcarbamoyloxy) -phenyl) -carbamate methyl N- (3- (N'-3-methylphenylcarbamoyloxy) -phenyl) -carbamate methyl-N- (3- (N'-4-) -carbamate fluorophenylcarbamoyloxy) phenyl) carbamate Methyl N- (3- (N'-3-chloro-4-fluorophenylcarbamoyloxy) - phenyl) carbamate

Ethyl-N- (3-N'-3-chloro-4-fluorphenylcarbamoyloxy) phenyl) -

carbamate

Ethyl N- (3-N'-3,4-difluorophenylcarbamoyloxy) -phenyl) -carbamate 20 Methyl N- (3- (N'-3> 4-difluorophenylcarbamoyloxy) -phenyl) -

carbamate

N-3- (4-fluorophenoxycarbonylaml.no) -phenylcarbamic acid methyl ester N-3- (2-methylphenoxycarbonylamino) -phenylcarbamic acid ethyl ester

N-3- (4-Pluorphenoxycarbonylamino) -phenylthiolcarbaminsäure-

methyl ester

Methyl N-3- (2,4,5-trimethylphenoxycarbonylamino) -phenyl-thiol-30-bamate

N-3- (phenoxycarbonylamino) -phenylthiolcarbaminsäure-methyl-

ester

N, N-diethyl-thiolcarbamic acid p-chlorobenzyl ester N, N-di-n-propyl-thiocarbamic acid ethyl ester N, N-di-n-propyl-thiolcarbamic acid n-propyl ester N, N-di-isopropyl-thiolcarbamic acid-2,3-dichloroallyl ester 5 N, N-Di-isopropyl-thiolcarbamic acid 2,3,3-trichloroallyl ester

N, N-Di-isopropyl-thiolearbamic acid 3-methyl-5-isoxazolyl-methyl ester N, N-di-isopropyl-thiocarbamic acid S-ethyl - ^ - isoxazolyl

methyl ester

N, N-di-sec-butyl-thiocarbamic acid ethyl ester N, -di-sec-butyl-thiocarbamic acid benzyl ester N-ethyl-N-cyclohexyl-thiocarbamic acid ethyl ester N-ethyl-N-bicyclo- [2,1,13 heptyl-thiolcarbaminsäureethylester

S- (2,3-dichloroallyl) - (2,2 _J 4-trimethyl-azetidine) -l-carbo-

thiolate

S- (2,3,3-trichloroallyl) - (2,2,4-trimethyl-azetidine) -l-carbothiolate

S ~ Eth'yl-hexahydro-1-H-azepine-1-carbothiolate S-benzyl-3-methyl-hexahydro-1-H-azepine-1-carbothiolate

S-Beпzyl-2,3-dimethylhexahydro-l-H-l-carbothiolate azepiп-

S-ethyl-Smethylhexahydro-l-H-l-carbothiolate azepln-

N-ethyl-Nn-butyl-thiolcarbamic acid n-propyl ester N, N ~ dimethyl "dithiocarbamic acid 2-chloroallyl ester N-methyl-dithiocarbamic acid sodium Trichloroacetic acid Na salt ^, <-, Dichloropropionic acid Na salt t ^^ -Dichlorbuttersäure Na salt

ο ^, ο ^, β, β-tetrafluoropropionic acid sodium salt o-methyl-1,3-dichloropropionic acid sodium salt c-chloro-β-i-chloro-phenyl-propionic acid methyl ester o-β-dichloro-β- phenylpropionic acid methyl ester benzamido-oxy-acetic acid

(Salts, esters, amides)

(Salts, esters, amides)

(Salts, esters, amides)

(Salts, esters, amides)

(Salts, esters, amides)

(Salts, esters, amides)

2,3,!> - Tri: Lodbenzoic acid 2,3,6-trichlorobenzoic acid 2,3,5,6-tetrachlorobenzoic acid

2-Methoxy-3,6-dichlorobenzoic acid 5 2-Methoxy-3,5,6-trichlorobenzoic acid 3-Amino-2,5,6-trichlorobenzoic acid

OjS dimethyl tetrachlorothioterephthalate dimethyl 2,3,5,6-tetrachloro-terephthalate disodium 3,6-endoxohexahydrophthalate 4-araino-3,5,6-trichloro-picolinic acid (salts) 2-cyano-3 - (N-methyl-N-phenyl) -amino-ethyl acrylate ethyl 2- [4- (4'-chlorophenoxy) -phenoxy-2-propionic acid isobutyl ester 2- [4- (2 ', 4'-dichlorophenoxy) -phenoxy] -propionic acid methyl

ester

2- [4- (4'-Trifluoro-methyl-phenoxy) -phenoxy] -propionic acid

methyl ester

2- [4- (2'-chloro-4'-trifluorophenoxy) -phenoxy] -propionic acid-Na-salζ

2- [4- (3 ', 5'-dichloropyridyl-2-oxy) -pnenoxyj-propionic acid

Na salt

2- (N-benzoyl-3,4-dichloro-phenylamino) -propionic acid ethyl ester

2- (N-benzoyl-3-chloro-4-fluoro-phenylamino) -propionic acid

methyl ester

2- (N-benzoyl-3-chloro-4-fluoro-phenylamino) -propionic acid

isopropyl

2-Chloro-4-ethylamino-6-isopropylamino-1,3,5-triazine 2-Chloro-4-ethylamino-6- (amino-2'-propionitrile) -1,3,5-triazine

2-chloro-4-ethylamino-b-2-methoxypropyl-2-amino-1,3,5-triazine

2-chloro-4-ethylamino-6-butyn-1-yl-2-amino-1, 3,5-triazine 2-chloro-4,6-bisethylamino-1,3,5-triazine 2-chloro-4, 6-bis-isopropylamino-1,3,5-triazine г-СЫог - ^ - ізоргоруіатіпо-б-сусіоргоруі amino-1 j 3,5-triazine 5 г-Агіао-Д-те ^ уіатіпо-б-ізоргоруі amino-1,3 , 5-t riazine 2-methylthio-4-ethylamino-6-isopropylamino-1,3,5-triazine 2-methylthio-4-ethylamino-6-tert-butylamino-1, 3,5-triazine 2-methylthio-4 , 6-bisethylamino-1,3,5-triazine 2-methylthio-4,6-bisisopropylamino-1,3,3-triazine

2-methoxy-4-ethylamino-6-isopropylamino-1,3,5-triazine 2-methoxy-4,6-bisethylamino-1,3,5-triazine 2-methoxy-4,6-bis-isopropylamino-1,3, 5-triazine 4-amino-6-tert-butyl-3-methylthio-4,5-dihydro-i, 2,4-triazin-5-one

4-Amino-6-phenyl-3-methyl-4,5-dihydro-l, 2,4-triazin-5-one 4-isobutylideneamino-6-tert-butyl-3-methylthio-4,5-dihydro-

1,2,4-triazine-5-one

1-methyl-3-cyclohexyl-6-d! methyl-amino-1,3,5-triazine-2,4-

-dione

S-tert-butyl-S-chloro-o-methyluracil S-tert-butyl-S-bromo-6-methyluracil

S-sec-butyl-S-bromo-o-methyl uracil

3- (2-Tetrahydropyranyl) -5-chloro-6-methyluracil 3- (2-Tetrahydropyranyl) -5,6-trimethylenuracil -S, 6-trimethylenuracil

2-? 4-ethyl-4- (3'-trifluoromethylphenyl) -tetrahydro-1, 2,4-oxadiazine-3,5-dione

2-methyl-4- (4'-fluorophenyl) -tetrahydro-l, 2,4-oxadiazine-3> 5-dione

3-amino-1, 2,4-triazole 35

1-Allyloxy-1- (4-bromophenyl) -2- [1 ', 2', 4'-triazolyl-d ¹ ) _] _ ethane (salts)

[-l- (1,2,4-triazolyl-1 ')] - [1 (4'-chlorophenoxy)] - 3,3-dimethylbutan-2-one N, N-diallyl chloroacetamide

N-Isopropyl-2-chloroacetanilide N- (Butyn-1-yl-3) -2-chloroacetanilide

2-methyl-6-ethyl-N- (propargyl) -2-chloroacetanilide 2-methyl-6-ethyl-N- (ethoxymethyl) -2-chloroacetanilide

2-methyl-6-ethyl-N- (2-methoxy-l-methylethyl) -2-chloroacetanilide

2-methyl-6-ethyl-N- (lsopropoxycarbonylethyl) -2-chloroacetanilide

15 2-Methyl-6-ethyl-N- (4-methoxypyrazol-1-yl-methyl) -2-chloro-acetanilide

2-Methyl-6-ethyl-N- (pyrazol-1-ylmethyl) -2-chloroacetanilide 2,6-Dimethyl-N- (pyrazon-1-ylmethyl) -2-chloroacetanilide 2,6-Dimethyl- N- (4-methyl-pyrazol-l-yl-methyl) -2-chloro-

acetatanilid

2 _> 6-Dimethyl-N- (1,2,4-triazol-1-ylmethyl) -2-chloroacetanilide

2,6-dimethyl-N- (3,5-d] methylpyrazol-1-ylmethyl) -2-chloro

acetanllid

2,6-dimethyl-N- (1,3-dioxalan-2-yl-methyl) -2-chloracetanilld

2,6-Dimethyl-N- (2-methoxyethyl) -2-chloroacetanilide 2,6-Dimethyl-N- (isobutoxymethyl) -2-chloroacetanilide 2,6-Diethyl-N- (methoxymethyl) -2-chloroacetanilide 2 _} 6 -Dlethyl-N- (n-butoxymethyl) -2-chloroacetanilide

2 _J 6-diethyl-N- (ethoxycarbonylmethyl) -2-chloroacetanilide 2,3,6-trimethyl-N- (pyrazol-1-ylmethyl) -2-chloroacetanilide 2 _> 3-dimethyl-N- (isopropyl) - 2-Chloroacetanilide 2,6-Diethyl-N- (propoxyethyl) -2-chloroacetanilide

2- (2-methyl-4-chlorophenoxy-N-methoxy-acetamld

2- (oc-naphthoxy) -N, N-diethylpropionamide 2,2-diphenyl-N, N-dimethylacetamide "* (3 > 4 > 5-tribromopyrazol-1-yl) -N, N-dimethylpropionamide N- (I, 1-dimethylpropynyl) -3,5-dichlorobenzamide N-1-naphthylphthalamic acid Propionic acid 3,4-dichloroanilide Cyclopropanecarboxylic acids 4-dichloroanilide Methacrylic acid 3,4-dichloroanilide 2-Methylpentanecarboxylic acid 3,4-dichloroanilide N-2,4-dimethyl 5- (trifluoromethyl) sulfonylamino-phenylacetamide

N-4-methyl-5- (trifluoromethyl-sulfonylamino-phenylacetamide

2-propionyl-amino-4-methyl-5-chloro-thiazol

0- (methylsulfonyl) -glycolic acid N-ethoxymethyl-2,6-dirae-thyl-15-anllide

0- (methylaminosulfonyl) polyglycolic-N-isopropyl anilide

0- (i-propylaminosulfonyl) polyglycolic-N-butyn-l-yl-3-anilide

0- (methylaminosulfonyl) -glycolic acid hexamethyleneimide 2,6-dichloro-thiobenzamide 2,6-dichlorobenzonitrile

3,5-dibromo-4-hydroxy-benzonitrile (salts) 3,5-diiodo-4-hydroxybenzonitrile (salts)

3,5-dibromo- ¹ -hydroxy-0-2,4-dinitrophenyl benzaldoxime (salts)

3,5-Dibrora-4-hydroxy-0-2-cyano-4-nitrophenylbenzaldoxime (salts)

Pentachlorophenol-Na salt

2,4-dichlorophenyl-4'-nitrophenyl ether 2, k, 6-trichlorophenyl-4'-nitrophenyl ether 2-fluoro-4,6-dichlorophenyl-4'-nitrophenyl ether 2-chloro-4-trifluoromethylphenyl-4'-nitrophenyl ether 2, 4'-Dinitro-4-trifluoromethyl-diphenyl ether 2,4-dichlorophenyl-.3'-methoxy-4'-nitro-phenyl ether

2-chloro-4-trifluormsthylphenyl-3'-ethoxy-4'-nitro-phenyl-

ether 35 2-Chloro-4-trifluoromethyl-phenyl-3'-carboxy-4'-nitro-phenyl

ethers (salts)

2,4-dichlorophenyl-3'-methoxycarbonyl-4'-nitro-phenyl ether

2- (з, 4-dichlorophenyl) -4-methyl-l, 2,4-oxadiazolidine-3,5-

dione 5 2- (3-tert-butylcarbamoyl-oxyphenyl) -4-methyl-1,2,4-oxadia

zolldin-3,5-dione

2- (3-isopropyl-oxyphenyl) -4-methyl-1,2,4-0xadia-

zolldin-3,5-dione

2-phenyl-3, 1-benzoxazinone- (4) 10 (4-bromophenyl) -3,4,5,9,10-pentaazatetracyclo- [5,4,1, O ² '' O,

^{8> 11} ] -dodeca-3,9-diene

2-Ethoxy-2,3-dihydro-3,3-dimethyl-5-benzofuranyl-methane-sulfonate

2-Ethoxy-2 _J 3-dihydro-3,3-dimethyl-5-benzofuranyl-dimethyl-15-aminosulfate

2-ethoxy-2,3-dihydro-3,3-dimethyl-5-benzofuranyl- (N-methyl)

N-acetyl) -aminosulfonat

3,4-dichloro-1,2-benzisothiazole N-4-chlorophenyl-allyl-succinimide 2-methyl-4,6-dinitrophenol (salts, esters) 2-sec.butyl-4,6-dinitrophenol (salts ^ ester) 2- sec-Butyl-4,6-dinitrophenol acetate 2-tert-butyl-4,6-dinitrophenol acetate 2-tert-butyl-4,6-dinitrophenol (salts) 2-tert-butyl-5-methyl-4, 6-dinltrophenol (salts) 2-tert-butyl-5-methyl-4,6-dinitrophenol acetate

2-sec.amyl-4,6-dinitrophenol (salts, esters) 1- (o, oc-dimethylbenzyl) -3- (4-methylphenyl) urea l -phenyl-3- (2-methylcyclohexyl) urea 1-phenyl-1-benzoyl-3,3-dimethylurea 1- (4-chlorophenyl) -1-benzoyl-3,3-dimethylurea 1- (4-chlorophenyl) -3,3-dimethylurea 1 - (4-chlorophenyl) -3mM: methyl-3-butyn-1-yl-3-urethane-tofl- (3,4-dichlorophenyl) -3,3-dlmethylurea

l -. (3,4-dichlorophenyl) -1-benzoyl-3,3-d-imethyl-urethane t-butyl (3,4-dichlorophenyl) -3-methyl-3-n-butyl-urea 1- (4- i-propylphenyl) -3,3-d imethylurea 1- (3-trifluoromethylphenyl) -3,3-dinethylurea 5 l- (3-o4oc, β-β-tetrafluoroethoxyphenyl) -3,3-dimethylurea 1- (3-tert-butylcarbamoyloxy-phenyl) -3,3-dimethyl-hamsoff l- (3-chloro-4-methylphenyl) -3,3-dimethyl-urea 1- (3-chloro-4-) methoxyphenyl) -3,3-d-imethylurea l- (3,5-dichloro-4-methoxyphenyl) -3,3-dimethylurea

1- [4- (4'-chlorophenoxy) -phenyl] -3,3-dimethyl-urea [4- (4'-methoxyphenoxy) -phenyl] -3,3-dimethyl-urea 1-cyclooctyl-S-dimethyl-urea

1- (hexahydro-4,7-methanindan-5-yl) -3,3-dimethylurea 1- [1- or 2- (3a, 4,5,7,7a-hexahydro) -4,7-methanoindanyl ] -

-3,3-dimethyl-urea f

1- (4-fluorophenyl) -3-carboxymethoxy-3-methyl-urea 1-phenyl-S-methyl-S-methoxy-urea 1- (4-chlorophenyl) -3-methyl-3-methoxy-urea 1- ( 4-bromophenyl) -З-те ^ уі-З-thethoxy-urothioyl (3,4-dichlorophenyl) -3-methyl-3-methoxy-urea

1- (3-Chloro-4-bromophenyl) -3-methyl-3-methoxy-urea 1- (3-chloro-4-isopropyl-phenyl) -3-methyl-3-methoxy-urea 1- (3-chloro-4 -raethoxyphenyl) -3-methyl-3-methoxy-urea 1- (3-tert-butylphenyl) -3-methyl-3-methoxy-urea

1- (2-Benzothiazolyl) -1,3-dimethyl-urea 1- (2-benzthiazolyl) -3-methyl-urea 1- (5-trifluoromethyl-1,3,4-thiadiazolyl) -l, 3-dimethyl- -urea imidazolidin-2-on-l-carboxylic acid iso-butyl-amide l, 2-dimethyl-3,5-diphenylpyrazolium "methylsulfate l, _{2-4-trimethyl-3}} 5-diphenylpyrazolium methyl sulfate 1,2-Dimethy1-4 -bromo-3j5-diphenylpyrazolium methylsulfate l, 3-Dimethyl-4- (3,4-dichlorobenzoyl) -5 - [(4-methylphenylsulfonyl) oxy] pyrazole

2,3,5-trichloro ~ pyridinol- (4)

- ^ - (3'-t rif luormethylphenyl) -pyridone- (4)

l-methyl-4-phenyl-pyridinium chloride

1,1-Dlmethylpyridiniumchlorid

S-Phenyl - ^ - hydroxy-o-chloropyridazine I _J -dimethyl-4,4'-dipyridylium di (methylsulfate)

1,1'-di (3,5-dinethylmorpholin-carbonylmethyl) -4,4-di-

pyridylium dichloride

1,1'-Ethylene-2,2'-d-ipyr idylium-d ib romide

3- [l (N-ethoxyamino) -propylidene] -6-ethyl-3,4-dihydro-2-H-10-pyran-2,4-dione

-3_ [l_ (N-Allyloxyamino) -propylidene] -6-ethyl-3,4-dihydro-2-

-H-pyran-2,4-dione

2-C 1- (N -allyloxyamino) -propylidene] -5,5-dimethyl cyclohexane

1,3-dione (salts) 15 2- [1- (N-allyloxyamino-butylidene) -5,5-dimethyl cyclohexane

-1,3-dione (salts)

2- [1- (N-Allyloxyamino-butylidene) -5,5-dimethyl-4-methoxycarbonyl-cyclohexane-ljS-dione (salts)

2-chlorophenoxyacetic acid (salts, esters, amides)

4-chlorophenoxyacetic acid (salts, esters, amides)

2,4-dichlorophenoxyacetic acid (salts, esters, amides)

2,4,5-Trichlorophenoxyacetic acid (salts, esters, amides) 2-Methyl-4-chlorophenoxyacetic acid (salts, esters, amides) 3,5,6-Trichloro-2-pyridinyl-oxyacetic acid (salts, esters, amides)

j ^ -Naphthoxyessigsäuremethylester

2- (2-methylphenoxy) propionic acid (salts, esters, amides)

2- (4-chlorophenoxy) propionic acid (salts, esters, amides)

30 2- (2,4-dichlorophenoxy) -propionic acid (salts, esters, amides)

2- (2,4,5-trichlorophenoxy) -propionic acid (salts, esters,

amides)

2- (2-methyl-4-chlorophenoxy) -propionic acid (salts, esters,

Amides) 4- (2,4-dichlorophenoxy) butyric acid (salts, esters, amides)

4- (2-methyl-4-chlorophenoxy) -butyric acid (salts, esters, amides)

Cyclohexyl-3- (2,4-dichlorophenoxy-acrylate) 9-Hydroxyfluorene-carboxylic acid- (9) (salts, esters) 2,3,6-Trichlorophenyl-acetic acid (salts, esters) 4-Chloro-2-oxo-benzothiazoline 3-yl-acetic acid (salts, esters)

Gibelleric acid (salts)

Disodium methylarsonate monosodium salt of methylarsonic acid

N-phosphono-methyl-glycine (salts)

N, N-bis (phosphono-methyl) -glycine (salts)

2-Chloroethanephosphonic acid 2-chloroethyl ester Ammonium ethyl-carbamoyl-phosphonate Di-n-butyl-1-n-butylamino-cyclohexyl-phosphonate Trithiobutyl phosphite

0, O-diisopropyl-5- (2-benzosulfonylamino-ethyl) -phosphordithionat

2,3-dihydro-5,6-dimethyl-1,4-dithiine-l, 1,4,4-tetraoxide 5-tert-butyl-3- (2,4-dichloro-5-isopropoxyphenyl) -l, 3 , 4-oxadiazolone- (2)

4,5-dichloro-2-trifluoromethylbenzimidazole (salts)

l, 2,3,6-tetrahydropyridazine-3,6-dione (salts)

Succinic mono-N-dimethylhydrazide (salts)

(2-chloroethyl) trimethylammonium chloride (2-methyl-4-phenylsulfonyl) trifluoro ^{<methanesulfonanilide} 1,1-dimethyl-4,6-diisopropyl-5-ium indanylethylketon Na tr chi о rat

Ammonium Rhodanide Oalcium Cyanamide

2-chloro-4-trifluoromethyl-3-ethoxycarboпyl-4'-nitrophenyl

ether

l- (4-3enzyloxyphenyl) -3-methyl-3-methoxyurea

2- [1- (2,5-dimethylphenyl) -ethylsulfonyl] -pyridine-N-oxide 35

2-chloro-4-trifluoromethylphenyl-3'-2-fluoroethoxy-4'-nitro-phenyl ether

2-chloro-4-trifluomethylphenyl-3 (ethoxycarbonyl) methylthio-4-nitrophenyl ether

5 2,4,6-trichlorophenyl-3 (ethoxycarbonyl) methylthio-4-nitrophenyl ether

2- [1- (N -ethoxymino) -butylidene] -5- (2-ethylthiopropyl) -3-hydroxy-cyclohexene-2-one (1) (salts) 2- [1- (N-ethoxymno ) -butylidene] -5- (2-phenylthiopropyl) -3-hydroxy-cyclohexene (2) -one (I) (salts)

Moreover, it is useful to use the novel compounds according to the invention, alone or in combination with other herbicides, also with other crop protection agents.

15 mixes muster, for example, with agents for controlling pests or phytopathogenic fungi or bacteria. Also of interest are the miscibility with mineral solutions, which are used for the elimination of nutritional or trace element deficiencies. To

It is also possible to add oils of various types, oil concentrates, wetting agents or adhesives as well as antifoams to the individual active substances or mixtures.

As fungicides, the new compounds act in particular against rust diseases; For example, a protective scion treatment against Erysichus graminis on barley and wheat is possible.

Claims (1)

Sans invention Pruch Herblzides agent, characterized by a content of
a solid of the liquid carrier and a substi-5-tanned urea of the formula I. R ¹ O 0 R ² // VnH-C-N I, W \ з ro χ wherein R is either a substituted phenyl radical of the formulas R \, R ¹ R ^? " -fi Vr" or - / ^ AR R "'R" · R "' in which R ¹ , R "and R"'are each independently Is hydrogen, halogen, nitro, lower alkyl, lower alkyl, cyano, lower alkoxy, haloalkoxy, lower alkylmercapto, niadrigalkylsulphinyl or lower alkylsulphonyl, or represents an optionally substituted Hateroarylrest stands. R is hydrogen, lower alkoxy], lower alkoxy, lower alkenyl, lower alkynyl, cycloalkyl or optionally substituted phenyl, F. hydrogen or Nieörj ^ alkyl, where R ² чпа R ^) together a for chamethylene or Oxaoli ^ ornethylene can stand and X hydrogen, rlsloean, mitco, ^ isirigalky; Haloalkyl, nydigalkalkyi, haloalkyl, or Cyan bedcut-t.
3b