DE2117662A1 - Phenylurea derivatives, their production and use as herbicides - Google Patents

Description

Pheny! Urea derivatives, their production and use as herbicides

It is already known (DOS I.909.52I of September 10, I97O), N-arylureas the general formula

wherein X ₁ and X _{0 are} trifluoromethoxy, chlorine and hydrogen and

X or X is trifluoromethoxy, £ 1

R for hydrogen, alkyl (lk carbon atoms) or alkenyl

(2-k carbon atoms) stands and
R ₀ for alkyl (1-4 carbon atoms) or alkenyl (2-k carbon atoms)

stands

and use them as herbicides.

Despite partly good herbicidal! · Properties is the Uirluing of these compounds vowed against a number to be combated

209843/1159 BAD ORfGtNAL

Weeds and their selectivity in some crops, e.g. cotton, are not always sufficient.

The present invention relates to new phenylurea derivatives the general formula

in which X and X _{0 are} hydrogen or the difluorochloro-r.iothoxy-

Group -ClF CO and X. is not the same as X,

R represents hydrogen or alkyl with 1-4 carbon atoms, preferably

Methyl, stands and
R _{2 is} alkyl (C ₁ -C ₄ ), alkenyl (C ₂ -C ₄ ), alkynyl (C ₂ -C ₄ ) or OCIi ₃

means and processes for their preparation, which are characterized in that one

a) meta- or para-difluorochloro-methoxy-phenyl-isocyanate or meta- or para-difluorochloromethoxy-carbanilic acid chlorides with corresponding primary or secondary amines or with O-methyl- or N-methyl- or G, N-dimethylhydroxylakine implements and, if necessary, a Nachalkylieiing undertakes, or

b) meta- or "para-difluorochloromethoxy-aniline with corresponding Alkyl, alkenyl or alkynyl isocyanates or with corresponding dialkyl, alkyl-alkenyl or Alkyl-alkynyl-carbamic acid chlorides or with methyl methoxy-carbamic acid phenyl ester implements.

These urea derivatives are superior to the herbicides mentioned above in their weed control effect. The invention therefore further provides herbicidal compositions which are characterized by a content of one of the aforementioned

ORIGINAL BATHROOM

209843/1159

_ O "

Difluurochloromethoxy-phenyl-urea derivatives as an active ingredient in addition to Xetz, adhesives, dispersants, liquid or solid Carrier materials, grinding aids, granulating agents or other biocidal active ingredients and / or fertilizers as well as the Use of these agents to combat undesirable vegetation .

The following formula pictures illustrate the production of some of the claimed new urea derivatives:

ClF ₀ CO

.X = C = O

IiX:

cn.

CH.

ClF ₀ CO

ClF ₀ CU

N = C = O +

ClF ₀ CO

ClF ₀ Cl?

209843/1 1 B9

BATH ORIGINAL

ClF ₂ CO-Zj) -N = C = O + H ₂ N-OCH ₃ >> ClF ₂ CO- (T) N-NH-CN

.H
'OCH,

Dimethyl sulfate

CH ₃ OH / NaOH

ClF ₈ CO-A J) -N = C = O + NH ₂ OH >> ClF ₂ CO- (TJ) -NH-CN

-0H

, CO-Zj) -NH-C-N;

W δ

.CH ₃

Dimethyl sulfate

CIF ^ CO-Zf J) -N = C = O + HN '

-CH ₃ OH

CH ₃ OH / Na OH

^ CH ₂

ClF ₂ CO

-NH-C-Cl + ΗΝ. '

It

ClF ₂ CO-

-NH-C-NC ^ δ

The reactions of the m- or p-difluorochloromethoxyphenyl isocyanates or carbamic acid chlorides with the amines or the alkylated hydroxy! amines are advantageous at temperatures carried out from about 0 to +80 C with or without a diluent. Suitable diluents are, for example, toluene and benzene or dioxnn.

The corresponding reactions with hydroxylamine take place advantageously .in a two-phase mixture of water and one with Water immiscible organic solvents at temperatures from about U to + 'K)' 'C.

The alkylation takes place with dialkyl sulfals, alkyl halides or alkyltolene sulfonates. It is advantageous in aqueous alkaline Suspension or carried out in mixtures of aqueous alkali and an organic solvent. Appropriately done the addition of the alkali and the alkylating agent simultaneously with pH control; but you can also use the urea either submit together with the alkylating agent in an organic solvent and then the alkali admit, or proceed in reverse order. The reaction temperature naturally depends on the reactivity dos the alkylating agent used and is between 10 and 90 C.

The meta- or para-difluorochloromethoxyphenyl isocyanates required as starting materials for the production of the claimed new urea derivatives are obtained in good yields by reacting the meta-difltiorchloromethoxy-benzoyl fluoride or the para-isomer (produced by partial fluorination of the corresponding trichloromethoxybenzoyl chlorides with hydrogen fluoride at temperatures between 90 100 ° C) with sodium azide in inert solvents (toluene, xylene) and thermal circulation; ierung <! Or intermedia * - resulting difluorochloromethoxylipuzoyla / ίde to (ion corresponding isocyanates with nitrogen elimination (Curtius' choror degradation). For recovery the beanr.pruclton

BATH ORIGINAL

9BA 3/1159

Urea is needed as intermediate products Isocyanates not to isolate, but sets them, after filtering off the box of the reaction and sodium fluoride formed possibly excess sodium azide - expedient in the chosen one Solvent with suitable amines. Of course, you can also distill off the solvent and the respective Obtain isocyanate by fractional distillation.

The new compounds have a good effect against weeds and are important in their gentle properties Crops such as cotton, grain, rice, corn, and peanut Legumes such as peas and beans are known ilericides such as the corresponding trifluoromethoxy compounds or the fluorine fluorine think.

The compounds according to the invention can be used as wettable powders, emulsifiable concentrates, sprayable solutions, dusts or granules are used. Wettable powders are in Preparations that are uniformly dispersible in water and which, in addition to the active ingredient, contain a diluent or inert substance, wetting agents, e.g. polyoxyethylated alkylphenols, polyoxyethylated oleyl or stearylamines, alkyl or alkylphenyl sulfonates and Dispersants, e.g. sodium lignin sulfonic acid, 2,2'-dinaphthylmethane-6, Sodium 6'-di-sulfonic acid, dibutylnaphthalene sulfonic acid Sodium or oleylmethyltauric acid "es sodium contain.

Emulsifiable concentrates are made by dissolving the active ingredient in an organic solvent, e.g. butanol, cyclohexanone, Obtain dimethylformamide, xylene or higher-boiling aromatics. In order to obtain good suspensions or emulsions in water " rich, air earths continue to add wetting agents from the series mentioned above.

Dusting agents are obtained by grinding the active ingredients with fine distributed solid substances, e.g. talc, natural clays such as

209843/1159

Kaolin, dentonite, pyrophillite or dietoine earth. Sprayable Solutions that are often traded in aerosol cans contain the active ingredient dissolved in an organic solvent, next to it is e.g. a mixture of chlorofluorocarbons as fuel. Granules can either be converted into adsorptive, granulated form by dissolving the active ingredient Incrtniatcrial or by applying Active ingredient concentrates using adhesives, e.g. polyvinyl alcohol, polvficrylsaurem sodium or mineral oils on the Surface of carrier materials such as sand, kaolinite or of granulated inert material. Suitable active ingredients can also be used in the usual for the production of fertilizer granules Way - if desired in a mixture with fertilizers - produced will.

In the case of herbicidal agents, the concentrations of the active ingredients in the commercially available formulations can be different.

In wettable powders, the active ingredient concentration varies, for example, between about 10 % and 95%. The remainder consists of the formulation additives given above. In the case of emulsifiable concentrates, the active ingredient concentration is about 10 % to 100 % - 20% of active substance, sprayable solutions approximately 2 · -. 20% Hei granules the active compound content depends partly on whether the active compound is liquid or solid and are fillers u w _s used which granulation..

The commercially available concentrates are used if necessary I κ diluted in the usual way, e.g. in the case of wettable powders and emulsifiable concentrates with water. Dusty and granulated preparations as well as sprayable solutions Do not dilute with other inert substances before use · With external conditions such as temperature, humidity among other things, the required application rate varies. It amounts to in al I mean about 0.015-0.25 g / φϋ, preferably 0.03-0.12 g Active ingredient per square meter.

2 0 9 8 4 3 / 1159- BAD ORIGINAL

In addition, the active compounds according to the invention can be used with others Herbicides and soil insecticides are combined.

Known herbicides that are suitable for a combination with the claimed new products include, for example:

Urea derivatives:

Triazine derivatives:

Urazil derivatives:. Pyrazone derivatives: growth substances preparations

Carbamic acid derivatives:

Dinitrophenol derivatives Noruron (N- (Hexahydro -k , 7-methanindanr 5-yl) -N ', N'-dimethylurea)

Cycluron (N-Cyclooctyl-N ', N'-dimethylurea)

Methabenzthiazuron (N- (2-Benzthiazolyl) -N ", N'-dimethylurea

Linuron, chloroxuron, monolinuron, fluonieturon, diuron;

Simazine, atrazine, ametryn, prometryn, desmetryn, methoprotryn; Lenacil, bromacil;

1-phenyl -k- amino-fj-chlorpyrazidon- (6); 2, ^ - dichlorophenoxy-acetic acid, 4-chloro-2-methylphenoxy-acetic acid, 2,4,5-Ti'ichlorphenoxy-acetic acid, ^ -chloro ^ -methyl-phenoxy-butyric acid, 2,3,6-trichlorobenzoic acid , 2- (2-methyl-4-chlorophenoxy) propionic acid;

Barban, Phenmedipham, Triallat, Diallat, Vernolate,

OycIoate (N-Ethy1-N-cyclohexylthioethyl carbamate)

Monilate (ilexahydro-l-II-azepine-1-cai'baminsäurethioäthylester), EPTC (N'N-Dipropylthioäthylcarbamat),

Chlorproham and Swep;
: Dinitro-o-cresol, dinitro-sec.-butylphenol or dinoseb, dinoseb acetate;

BATH ORIGINAL

209ÖA3 / 11B9

Chlorinated aliphatic acids

Amides:

Dipyridilium compounds: anilides: sodium trichloroacetate and dalapon (2,2-dichloropropionic acid sodium) Amibcn (3-amino-2,5-dichlorobenzoic acid)

Picloram (4-amino-3,5,6-trichloropyridine ethyl propionamide); Diphenamide (N, N-diallylchloroacetadcJ Carbetamide (2- (plienylcarbamoyloxy) -N-ethylpropionamide)

N- (I, l-dimethylpropynyl) -3,5-dichlorobenzamide;

Paraquat, diquat, morfamquat; N- (3-dichlorophenyl) methacrylamide, Propanil, Solan, Monalide, 2-chloro-2 ', 6'-diethyl-N- (methoxymethyl) -acetanilide, Propachlor, methacryl-3,4-dichloroanilide; Dichlobenil, ioxynil;

Flurenol, Mononatriteimmethylarsonat, Trifluralin, Endothal (3,6-Endooxo-hexa-hydrophthalic acid), Nitrofen (2,4-dichlorophenyl-4 '-niti-o-j) henyl ether), Pyriclor (2, 3, 4-trichloro-4-pyridinol) and c <- (2,2,2-triehloroethyl) -styrene, Bensulide, aminotriazole.

There is another form of application of the present active ingredients in their mixture with fertilizers, whereby fertilizing and herbicidal agents are obtained at the same time.

Nitrile: Other preparations:

BATH ORIGINAL

209843/1 1 59

ExampleΊ

In a 1 liter four-necked flask with reflux condenser, dropping funnel and thermometer, 42 g (0.05 mol) of sodium azide are slurried in 350 ml of dry toluene and the mixture is heated ^{to 105 ~ 110 ° C. with vigorous stirring.} 112.5 S (θ, 5 mol) 3-T ^r ifl ^u - ^or chloromethoxy-benzoyl fluoride ( _{boiling point 760} 197-98 °, nf = 1.4612), diluted with 50 ml of dry toluene, are now slowly added dropwise. Vigorous development of nitrogen sets in after 1-2 minutes; the progress of the reaction is followed by means of a toluene-filled bubble counter connected downstream of the condenser, and the acid fluoride is added dropwise so quickly that the solvent refluxes gently. The dropping in is complete after about 40 minutes, and after a further 45 minutes no more nitrogen is developed. The reaction solution is cooled, and the salts (NaF and excess NaN ₃ ) are filtered off with suction and washed with a little dry toluene. The filtrate is halved (520 ml) and one half (260 ml) is transferred to a fresh 1 liter stirred flask;

After adding a few drops of triethylamine, 12 g (0.27 col) of dimethylamine, dissolved xnPToluene, are slowly added to the solution; The reaction mixture is thus heated up to 4O ⁰ C, and after a short time of the urea formed precipitates. It for 30 minutes then stirred at 35-40 ⁰ C, ABG "l: ühit, filtered off with suction, the reaction product and washed nit toluene. By concentrating the filtrate to about half and adding the same volume of petroleum ether (boiling range 60-9 ° C), another small amount of urea is obtained.
The substance is recrystallized from benzene / petroleum ether.

Yield: 53 g, mp 123-24 ⁰ C.

Analysis:

⁰ IF ₂ CO

-NH-C-N.

.CH,

"calc .: C = .45.4 <fo found . s C = -45.6 ^c / o H = 4.2 io H = 4.4 $

N = 10.6 yo N = 10.6 </ y

C ₁₀ H ₁₁ ClF ₂ N ₂ O ₂

MG 264.7

209 843/1159

Example 2

The second half of the reaction solution of example (l) (260 ml) is freed from the solvent in a rotary evaporator under a water jet vacuum and the remaining light brown clear OeI is fractionally distilled.

45 g are obtained

3-difluorochloroethoxyphenyl isocyanate with a boiling point of ₇ 76 ⁰ C,

20th
XL = 1.4904 »as a colorless, easily flowing oil.

45 g (O, 2O5 KoI) of the isocyanate are dissolved in 200 ml of absolute benzene and 15 »1 g (θ, 215 mol) of 0.11-dimethyl-hydroxylamine are added while stirring. Vigorous Wärnetönung, the temperature rises to 34 ⁰ C.,! Laughing liachrühren half an hour at the same temperature is cooled and the solvent distilled off under a slight vacuum. The first oily urea crystallizes soon by and is of gasoline (boiling range 60 - 9O ⁰ C) recrystallized.

Yield: 49 g of Pp 52 - 53 ⁰ C.

Analysis:

ClP ₂ CO

C ₁₀ H ₁₁ ClP ₂ Ii ₂ O ₃

calc .: F = 13.5 ti found : P = 13.3 N = 10.0 io Ή = 9.9

MG 280.7

Example 3

24.0 g (0.095 mol) of crude N-3-difluorochloromethoxyphenyl-N ^l -hydroxyurea, obtained analogously to Example (2) by reacting 22.0 g (0.1 mol) of 3-difluorochloroethoxyphenyl isocyanate with 4 , 0 g (0.12 mol) of hydroxylamine in benzene are taken up in 200 ml of methanol after the solvent has been stripped off. Now 24 ml of 10 n-liaOH and 30.2 g (0.24 LIoI) of dimethyl sulfate are simultaneously added dropwise from 2 dropping funnels, a p_ range of 9-10 being maintained. You can keep the

209843/1159

Temperatur.between 20 and 25 ° C and stir at the same temperature 2 hours after. Then it is diluted with 400 ml of ice water that precipitates Sucked off the reaction product, washed with ice water and made of n-hexane recrystallized.

Yield: 22 g, melting point 50-52 ° C

The urea is identical to that obtained from example (2). Of the The mixed melting point of the two substances did not result in any depression.

Example 4

chlorine In 250 ml of a toluene solution of 3-Difluoy'-methoxyphenyl isocyanate, prepared from 56.2 g (0.25 col) of 3 "" difluorochloromethoxy-benzoyl fluoride analogous to Example (1), z2.6 g (0, 26 mol) of N-methyl-butylamine, diluted with 25 ml of toluene, added dropwise. ^{The rapidly increasing reaction temperature is kept at 35-40 ° C.} by cooling with ice water, stirred for a further 1 hour at the same temperature after the dropwise addition, cooled, the urea which has crystallized out is suctioned off and another small fraction is obtained by concentrating the mother liquor. Uncrystallized from benzene / petroleum ether (1: 2).

Yield: 60 g, mp 108 ⁰ C.

Analysis: ■ ·

calc .: C = 50/9 jS found. : C = £ 51.2

ClF ₂ CO

H = 5.656 H = 5.7 *

C ₁₃ H ₁₇ ClF ₂ N ₂ O ₂ MW 306.8

ORIEiNAL INSPECTED

2098A3 / 1159

21 1 7 6 S 2

Example 5

By reacting 40.5 S (0.185 mol) of 5-difluorochloromethoxyphenyl isocyanate in 200 ml of dry toluene with 6.2 g (θ, 2 mol) of methylamine, dissolved in 30 ml of toluene, under the same reaction conditions as in the example (.4), and recrystallization of the * urea from benzene / petroleum ether (1: 1) is obtained

yield «
• 42 g from Pp I. Analysis: < f 7 " Il ClP ₂ CO ^ ⁰ C ₉ H ₉ ClP ₂ MG 250, 65 "1 = y O ₂

calc .: N = 11.2> i found. : II = 11.3 ^c ß> P = 15.2 9i P «15.4? Ί

Example 6

The same urea is obtained by dissolving 19.4 E (0.1 mol) of 3-Difluorochloromethoxyanilin in 100 ml of absolute benzene, adding a few drops of triethylamine and slowly dropping 6.0 g (0.105 mol) of methyl isocyanate, diluted with absolute benzene. The mixture is stirred for 3 seconds at 45 ~ 5 ^ ° C, the reaction solution is concentrated to about half in the rotary evaporator and the urea is ^{precipitated by adding the same volume of petroleum ether (, boiling range 60-90 0} IJJ.

Yield: 22 g, melting point IO4-06 ° C

The mixed melting point with the product shown in Example (5) was found no depression.

BAD ORrGMNAL

■ 20.9843 / 1159

Example 7

Analogously to example (1), 65 g (0.17 KoI) Ifa-azide, dissolved in 35O ml dry toluene, are converted at 105-110 ° C with a reading of 109 g (0.75 mol) p- Difluorchlormethox.y-bsnzoylfluorid (bp ₇₆₀ I99 - 2G0 ° C, n _'n = 1.4670). 85 ml of dry toluene in Upon completion of the reaction ■ is aspirated from the salts (llaF UaIT and _3), and these are nit 50 ml of dry toluene, the solvent is drawn off under a weak vacuum and recovered by fractional distillation

135 g

4-Difluorchloriaethoxy-phenyl-isocyanate with a boiling point of ₇ ^{79 - 8O 0} C, η ~ = 1.4920 as a colorless oil,

43.8 g (0.2 mol) of 4-Difluorchlorneth.oxY-phenyl isocyanate, dissolved in 200 dry toluene, are added dropwise with stirring with a solution of 9 »9 B (θ, 22 mol) of dimethylamine in 40 ml of toluene. The temperature rises rapidly up to 50 ⁰ G and after a few minutes the reaction product begins to out-vr -.- i- ^ allize. After that, nan. Has stirred for 30 minutes at the same temperature, it is cooled, the precipitated urea is suctioned off and washed with pO ml of toluene. Another small fraction is obtained by concentrating the filtrate in a water jet vacuum. The total amount is recrystallized from benzene / light gasoline (1: 2).

Yield: 47 g, mp 124-125 ⁰ C.

Analysis:

ClF ₂ CO

calc .: C = 45.4 fo
H = 4.2 #
fr = 10.6 ·; ',

found: C = 45.7 ^c / ° H = 4.2 $ Ή = 10.4 $

LIG 264.7

BADORiGJNAL

209 843/1159

Example 8

A mixture of 3.3.7 g (0.2 I.iol) of 4-biofluorochloro: r.ethoxy-aniline and 21.2 g (0.21 col.) Of triethylamine, dissolved in 1 o ml of dry benzene, 5 ^{;; C} C dropwise with a reading of 21.5 S (0 "2 mol) in 60 Dimothyl-carbamnsäurechlorid ir.l 3enzol dry, after which the mixture is stirred for 2 hours at 50 ⁰ C and 30 minutes under gentle reflux of the solvent, cools down and the benzene is distilled off under a low vacuum. The crystalline residue is treated with 2CO in cold water, filtered off with suction, washed with water until the filtrate is free of chloride ions and in vacuo over CaCl ₂ dried. After 2 recrystallization from Fenzol / Petrolether

Yield: 35 g, mp 123-125 ⁰ C..

The! .Lisch-ο /.:;. Jlzrunkt with the product prepared in example (7) resulted no depression; thus the two ureas are identical.

In a solution of 0.2 mol of p-difluorochloromethoxy-phenylcarb-

Aminic acid chloride in absolute toluene, prepared by adding dropwise a mixture of 38.7 g (C-, 2 I. * ol) 4-bifluorochlorosethoxy-aniline and 21.2 g (0.21 Hol) triethylamine, dissolved in IOC nl dry toluene, A mixture of 6.5 g (0.21 Hol) of Hethylaain is slowly added dropwise with stirring into a submitted solution, cooled to -5 to 0 ^° C., of 18.8 g (θ, 2 mol) of phosgene in 150 ml of absolute toluene and 21.2 g (0.21 LIoI) of triethylamine diluted with 50 ml of absolute toluene. The mixture is allowed to slowly come to room temperature, it is kept at 40-45 ° C. for a further 2 hours, cooled and worked up as in Example (8). The urea is converted twice from benzene.

BATH ORIGINAL

209843 / 11B9

Yield·. 35 g of m.p. 155 r 156

Analysis: = / -IiH-C-IIH-CH MG 3 65 ClF ₂ CO- / O ₂ Il
O 10 250, CgH ₉ ClF ₂ II ₂ example

calc .: N = 11.2 <p found . : H = 11.4 ^C / O F = 15.2 ^c / o F = 15.1 Io

Putting 40.5 g (0.185 mol) prepared in Example (7) 4-difluorochloromethoxy-phenyl isocyanate in place of 3 ~ I ^s omeren and otherwise operates EIIT same amounts and under the same reaction conditions as in Example (5), we obtain

Yield ί 41 8 N - ^ - Difluorochloromethoxy-phenyl ^ lT'-methyl urine

material of mp 155 -. 156 ⁰ C (from benzene).

The urea yields at the mixed melting point with that shown in example (9) Product no depression.

The ureas listed below were analogous to those described above Examples prepared and characterized by the melting points:

K- (3-difluorochloromethoxy-phenyl) -N'-methoxy-urea mp I06 - 10.7 ⁰ C

N- (3-difluorochloroethoxyphenyl) -N '-methyl-N' -butyn- (3) -yl- (2) -urea

M.p. 112 ° C

BATH ORIGINAL

20.9843 / 1 1 69.

¹ Jl

N- (4-Mf luorochloromethoxy-phenyl) -N'-methoxy-1-H-methoxy-urea

M.p. 75-76 ° C

14)

N- (4-difluorochloromethoxyphenyl) -N'-methyΪ-Ν ¹ -η-butylurea

Mp. 68 - 69 ⁰ C

15)

N- (4-bifluorochloromethoxy-pheny1) -N • -me thy1-N'-butyn- (5) -yl- (2) -urea M.p. 116-117 ° C

A powder which is easily dispersible in 7 / water is obtained by adding parts by weight of N- (5-difluorochloromethoxy-phenyI) -K, IT'-dimethylurea, 20 parts by weight of finely dispersed silica, 14.5 parts by weight of quartz flour, 5.0 parts by weight ITaHCO ₃ (stabilizer and grinding aid), 7 ^σ / ο dinaphthylmethane-disulphonic acid sodium (dispersant) and 5 »5 f = alkylnaphlhalin-sulphonic acid sodium (wetting agent) and grinds in a pin mill.

A dusting agent which is well suited as a herbicide is obtained by mixing 10 parts by weight of N- (4-difluorochloromethoxyphonyl) -N ', II ¹ -dimothylurea as active ingredient and 90 parts by weight of talc as inert substance and comminuting in a cross beater mill.

18)

Kininion concentrate consists of 15 parts by weight of N- (5-difluorochloro-

2098Λ3 / 11Β9 bad ORIGINAL

inetrioxj-phenyl) -IT'-methyl-IT ¹ -methoxy-urea, 75 parts by weight. Cyclohexanone as solvent and 10 parts by weight of polyoxyethylated ionylphenol (10 AeO) as emulsifier '.

Example I9

Seeds of various weeds and crops were sown in pots and covered flat with earth. On the same day 7fV "" suspended the in ".'asser Wettable powder formulations of the following active ingredients on the soil surface sprayed (pre-emergence or preenergence treatment):

ClF ₂ CO-

ill) F ₃ CO-

-IiH-C -N,

Il

(inventive)

("known from DOS I.909.521)

further

(III)

ClF ₂ CO

F ₃ C 0

.CH

-iTH-c-ν;

II

\ / ^CH 3

η -HTT- Π -TT

-ITH-C -Ν Ο

(according to the invention)

(known from DOS I.9O9.521)

The result was noted 5 weeks after the treatment. It is ± 1
the following table as the degree of damage in percent, ie
100 = plants completely killed, 0 = plants completely undamaged.

BATH ORIGINAL

209 843/115 9

Tabel

Pre-emergence effect on weeds and crops; Dosages in kg / ha active ingredient; Degree of damage in ° / o.

Plant species

0.3 0.15

II
0.3 0.15

III
0.3 0.15

Alopecurus
myosuroides 95 55 Amaranthus
retroflexua 100 95 Anthemis arvenais 100 75 Avena fatua 60 45 Chenopodium album 100 95 Datura stramonium 100 70 Echinocloa crus-galli 80 50 Eleusine indica 85 70 Ipomoea purpurea 100 85 Lespedeza stipulacea 100 95 Merourialis annua 100 90 Panicum dichotomi-
florum 95 85 Poa annua 100 95 Sesbania exaltata 100 95 Setaria faberii QO Θ5

80 55

95 40

100 90 100 90 95 80 100 100 75 55 80 70 95 75 100 95 100 50 100 100 65 40 100 95 90 65 100 75 35 30th 100 90 90 80 100 100 100 90 100 80 95 80 100 100 95 75 ' 100 95 100 80 100 95 70 65 100 70

IV
0.3 0.15

50

70

75 55 60 40 95 85 100 40 50 40 85 55 60 10 7.0 40 85 20th 100 75 80 40 60 20th 85 55

CD ISJ

Sinapia arvensis
Stellaria media
Xanthium spinosum

Average
Weed effect

100 100 100 95 ■ 100 95 75 6-5 100 100 100 90 100 95 90 65 100 95 10 0 80 60 10 10 94 , 8 82.2 83.0 66.4 97.5 85.8 73.4 . 46

^ Crops;
r 'Apium graveolens

Gossypium hirsutum
ivj Vicia faba

Pisum sativum

Phaseolus vulgaris
Ca> Glycine soy
_ ,, Arachis hypogaea

~ * Oryza sativa
cn

co Zea mays

Hordeum distichum
Triticum aestivum

10. 0. 80 50 0 0 20th 10 0 0 25th 15th 0 0 20th 10 20th 0 60 10 10 0 30th; 20th 10 0 30th 15th 25th 10 25th 15th 20th VJl 20th 10 25th 10 30th 20th 15th 0 55 20th 0 0 40 20th 0 0 10 0 0 0 0 0 20th 0 45 30th 40 20th 45 30th 10 0 55 30th 10 0 30th 20th 30th 10 70 50 40 10 40 30th 35 15th 05 60 30th 20th 55 30th

Show the 'results suggest that substances of the invention on average, a significantly "better weed ^ _4, show effective than the corresponding comparison means, so only half the dosage of the substance was I ^ tion as required by the Vergle..chsmittel II, In order to achieve an average damage of about 82 per cent; the difference between III and IV was even clearer. At the same time, the substances CF) and I were considerably more tolerant than the comparison agents towards a larger number of cultures - fs) plant.

Example 20

Substance III was mixed with the preparation in an analogous manner

(v) f ^) - NH-C-N = fluometuron

Il ^ ** QJT

0 ³ ""

compared on weeds and on cotton (Gossypium 'hirsutum). The weeds were the following types:

Eleusine indica Datura stramonium

Panicum dichotomiflorum Anoda cristata

Bromus tectorum Ipomoea purpurea

Echinocloa crus-galli Lespedeza stipulacea

Setaria faberii Sesbania exaltata

Phalaris paradoxa Xanthium spinosum

Digitaria sanguinalis Chenopodium album

Leptochloa dubia Araaranthus retroflexus

The average weed effect was 5 "fold after treatment at

III Y

0.3 kg / ha active ingredient 98.2 ^ 96.9 <f ₀ 0.15 """87.5 ^C A 86.6 io

The weed effect of both substances was thus about the same; On the other hand, the following damage was observed on cotton:

III Y

5.0 kg / h a Active ingredient 30th , 0 -J, 90.0 io 2.5 11 Il Il 20th , 0 io 75.0 io 1.25 M. Il Il 10 , 0 yes 40.0 io 0.6 Il Il Il 0 20.0 io 0.3 Il Il Il 0 10.0 io 0.15 Il Il Il 0 0

The substance according to the invention is therefore much safer to use than the product Pluometuron, which is frequently used in building numbers.

209843/115 9

Example 21

The substances

(TI)

ClF ₂ CO

-NH-CN _n Ö

.CH ₃

^ OCH,

(according to the invention)

(VII)

as

F ₃ CO

(VIII) ClF ₂ CO

(IX) F.CO

-NH-C-N

.CH,

rT

OCH,

.CH,

NH-CO-N

(from DOS I.909.521)

(genius of invention β)

(from DOS I.909.521)

applied. At a dosage of 1.25 kg / ha of active ingredient, 5 weeks were made The following results were found after the treatment (data ε.13 Schidigunrs degree in percent):

VI VII VIII IX

Ipomoea purpurea 100 0 80 20th Sinapis arvensis 100 95 100 100 Avena fatua 70 20th 80 40 Echinochloa crus-galli 90 20th 60 40 Poa annua 95 60 100 80 Anthemis arvensis 100 20th 100 60

The substances VI and VIII according to the invention were therefore clearly more effective than the respective corresponding preparations VII and IX.

209843/1 159

Claims (3)

Claims I. 2. Process for the preparation of compounds according to claim 1, characterized in that one a) meta- or para-fluorochloromethoxy-plienyl isocyanafce or meta- or para-Difluoz-chlorotnethoxy-carbanilsaurechloride with corresponding primary or secondary amines or with C-methyl- or N-methyl- or 0, N-dimethyl- hydroxylamine converts and, if necessary. Carries out a post-alkylation; or b) meta- or para-difluorochloromethoxyaniline with corresponding Alkyl, alkenyl or alkynyl isocyanates or with corresponding dialkyl, alkylalkenyl or Alkyl-alkynyl-carbamic acid chlorides or with methyl methoxy-carbaniinsäurephenylester implements. 3. Herbicidal agents, characterized by their content Compounds according to claim 1 as an active ingredient. 209843/1159 BATH ORIGINAL