IL34012A - Phenyl urea derivatives,their manufacture and application as herbicides - Google Patents

Description

V \ :\ PHENYL UREA DERIVATIVES THEIR MANUFACTURE AND APPLICATION AS HERBICIDES ia *3B?g ^oipp ma tmaan ms**1* .η.ν>τικ *?ο mT in 34012/2 The present invention relates to urea derivatives of the general formula in which R stands for alkyl having 2 to 4 earbon atoms or cycioalkyl of 3 or 4 carbon atoms which are substituted by 4 to 7 at halogen atoms,/leaeb 2 of wh ch are fluorine atoms; stands for hydrogen or chlorine and I¾2 stands for hydrogen, methyl or methoSy* The invention also relates to processes for the manufacture of the said urea derivatives by reacting correspondingly substituted 1) hale(cyclo)alkyl henyl isocyanatee or halo(cyclo)alky - carbanilic acid chloride with (a) methyl- or dlmethylanaine or ith 0-methyl- or 0, -dimethylhydroxylamine, (b) 0-me hy1hyd oxyIaminΘ or N-methylhydroxylamine with subsequent alkylation of the reaction product, (c) hydroxylamine with dialkylation of the reaction product, or or (b) with dimethyl- or methyXmetboxy-earbeunic acid - 1 A - phenyl ester.

The reaction can be illustrated by the following schemes using correspondingly substituted phenyl isocyanates or carbanilic acid halides: CF, 2) using corresponding anilines: The halogeno-alkylphenyl or halogeno-cycloalkylphenyl isocyanates or carbamic acid chlorides are advantageously reacted with the amines or alkylated hydroxylamines at a temperature below 80°C, in the presence or absence of a di The corresponding reactions with hydroxylamine are advantageously carried out at a temperature below 40°C in a two-phase mixture consisting of water aid an organic solvent immiscible with water.

The alkylations are preferably performed in aqueous-alkaline suspension or in mixtures consisting of aqueous alkali and an organic solvent. The alkali metal hydroxide solution and the alkylating agent are suitably added simultaneously with pH control. Alternatively, the urea can be first introduced into the reaction vessel together with the alkylation agent in an organic solvent and the alkali metal hydroxide solution can then be added or, in the case of compounds that are less sensitive towards alkalies, the components can be added in reverse order of succession. The reaction temperature depends, of course, on the reactivity of o the alkylation agent used and lies between 10 and 90 C.

Starting compounds to be used in the aforesaid processes are, for example: 3-(heptafluoro-isopropyl)-phenyl isocyanate 3-( 11 , 1 ' ,2 · , 3 * » 3 ' , 3 ' -hexafluoropropyl)-phenyl isocyanate 3-(pentafluoro-ethyl)-phenyl isocyanate 3-(1 ' » 11 ,2' ,2* -tetrafluoro-ethyl)-phenyl isocyanate 4-chloro-3-( 1 ', 1 ',2* , 21 -tetrafluoro-ethyl)-phenyl isocyanate 3-(1 ' , 1 ' -dichloro-21 ,2 ' ,2· -trifluoro-ethyl)-phenyl isocyanate or 3-(2'-chloro-11 ,1 ' ,2' ,2' -tetrafluoro-ethyl)-phenyl isocyanate.

The novel isocyanates are obtained by phosgenation of the corresponding amines or their hydrochlorides. Instead The alkylation in the above processes is carried out with alkyl sulfates, alkyl halides or alkyl-toluene sulfonates.

The novel compounds are obtained in good yields and constitute, almost without exception, crystalline compounds. They may be used in the form obtained or after, having been further purified by recrystallization from the usual organic solvents.

The products have a good action against undesired plant growth. They may be used in the form of wettable powders, emulsion concentrates, dusting powders or granules either alone or, if desired, in combination with other herbicides, soil insecticides or with fertilizers.

Wettable powders are preparations that can be uniformly dispersed in water and contain, besides an inert substance, a wetting agent, for example polyoxethylated alkylphenols, polyoxethylated oleyl- or stearylamines, alkyl- or alkyl-phenyl sulfonates and dispersing agents, for example the sodium salt of lignin-sulfonic acid, of 2,2'-dinaphthylmethane-6,6'-disulfonic acid, of dibutyl-naphthalene-sulfonic acid or sodium oleylmethyltauride .

Emulsion concentrates are obtained by dissolving the active ingredient in an organic solvent, for example butan-ol, cyclohexanone, dimethylformamide, xylene or aromatic hydrocarbons having a higher boiling point. To obtain suspensions or emulsions in water having good properties, wetting agents as specified above are also added.

Dusting powders are obtained by grinding the active ingredients with finely divided, solid substances, for example talc, natural clays, pyrophillite or diatomaceous earths . gredient on to an absorptive, granulated inert material, or fcy applying concentrates of the active ingredient to the surface of a granulated inert material with the aid of an adhesive, for example polyvinyl alcohol, the sodium salt of polyacrylic acid, or mineral oils. Alternatively, suitable active ingredients may be made into granules, if desired in admixture with fertilizers, in the manner commonly used for the manufacture of granulated fertilizers.

In the following known herbicides that can be combined with the novel compounds of the invention are enumerated by way of example: urea derivatives linuron, chloroxuron, mono- lihuron, fluometuron, diuron triazine derivatives simazin, atrazin, ametryne, prometryne, desmetryne, metho- protryne uracil derivatives lenacil, bromacil pyrazone derivatives 1 -phenyl-4-amino-5-chloro- pyridazone (6) (PCA) growth-promoting 2 , 4-dichlorophenoxy-acetic preparations acid (2 ,4-D) , 4-chloro-2- methylphenoxy-acetic acid (MCPA) , 2,4, -trichlorophenoxy- acetic acid (2,4, 5-T), 4- chloro-2-methylphenoxy-butyric acid (MCPB), 2, 3, 6-trichloro- benzoic acid (TBA) carbamic acid derivatives barban, phenmedipham, triall- ate, diallate, vernolate and 2-chloroallyl- ,N-diethyl-di- thiocarbamate (CDEC) dinitro-sec .-tmtylphenol (DNBP) , dinosel-acetate chlorinated aliphatic acids trichloroacetic acid, dala- pon amides diphenamide, ΪΤ,Ν-diallyl- chloroacetamide (CDAA) dipyridilium compounds paraquat, biquat, morfamquat anilides N-( 3 , 4-dichlorophenyl)-meth- acrylamide (DCMA) , propanil, solan, monalide nitriles dichlobenil, ioxynil other preparations flurenol When the active ingredients according to the invention are mixed with fertilizers, preparations are obtained which simultaneously have a fertilizing and a herbicidal effect.

The novel compounds of the invention have a good action against weeds, for example wild mustard, "barnyard grass, chickweed, annual meadow grass and corn camomile. They are superior to known urea derivatives, for example N-3-tri-fluoromethyl-phenyl-If ,Ν' -dimethyl urea (fluometuron) and N-3-trifluoromethyl-phenyl-N'-methyl-li'-methoxy urea, in their sparing properties for a number of important cultivated plants, for example cotton, maize, rice, oat, millet, carrot, and leguminosae.

The following examples illustrate the invention.

E x a m p l e 1 27 Prams (0.1 mole) of 3-(1 ' ,1 '-dichloro-2' ,2» ,2'-trifluoroethyl)-phenyl isocyanate were dissolved in 100 milliliters of absolute benzene and, while stirring, 3.5 grams (0.11 mole) of methylamine were added to the solution whereupon the mixture became warm. After cooling the tallized from carbon tetrachloride.

Yield 27 grams melting point H5-H6°C Analysis calculated 9.3$ N, C10H9C12P3N2° molecular weight 301 E x a m p l e 2 24.4 Grams (0.1 mole) of 3-0 ' , '-dichloro-2' ,2'2?-trifluoroethyl)-aniline were dissolved in 100 milliliters of absolute benzene and, while stirring, 6.3 grams (0.11 mole) of methyl isocyanate dissolved in 20 milliliters of absolute benzene were added to the solution. The mixture was heated for 60 minutes at 50°C, after cooling the separated reaction product was filtered off with suction and recrys-tallized from carbon tetrachloride.

Yield 22 grams melting point 1 4-H6°C A mixed melting point with the product of Example 1 did not show any depression.

E x a m p l e 3 27 Grams (0.1 mole) of 3-01 ,1 '-dichloro-2' ,2' ^'-trifluoroethyl) -phenyl isocyanate were dissolved in 100 milliliters of absolute benzene and, while stirring, 6.3 grams (0.14 mole) of dimethylamine were added to the solution. The formed crystals were filtered off with suction and re-crystallized from cyclohexanone.

Yield 29 grams melting point 106-108 C Analysis calculated 8.9$ N.. 9.6$ N, E x a m p l e 4 A solution of 14 grams (0.13 mole) of dimethyl-carbamic acid chloride in 50 milliliters of absolute "benzene was added at 40°C while stirring to a mixture of 31.7 grams (0.13 mole) of 3-0 ' ,1 ' ,-dichloro-2' ,2» ,2· -trifluoroethyD-ani-line, 11.3 grams (0.13 mole) of triethylamine and 100 milliliters of absolute benzene. The reaction mixture was maintained for 2 hours at 40°C. After cooling, the crystalline reaction product was filtered off with suction, washed with water until the wash water was free from chlorine and re-crystallized from cyclohexanone .

Yield 36 grams melting point 107-109°C A mixed melting point with the product of Example 3 did not show any depression.

E x a m p l e 5 22 Grams (0.1 mole) of 3- ' ,11 ,2'2'-tetrafluoroethyl)-phenyl isocyanate were dissolved in 100 milliliters of ab-. solute benzene and, while stirring, 5.3 grams (0.11 mole) of O-methylhydroxylamine were added dropwise. The reaction mixture was maintained for 60 minutes at 40°C. After cooling, the crystalline reaction product was filtered off with suction and recrystallized from benzene.

Yield 24 grams melting point 90-92°C Analysis calculated 10.5$ N, .6$ N, C10H10I,4N2°2 molecular weight 266 E x a m p l e 6 22 Grams (0.1 mole) of 3-01 , 1 f ,2 ' 2 ' -tetrafluoroethyl)-phenyl isocyanate were dissolved in 100 milliliters of ab Ο,Ν-dimethylhydroxylamine were added dropwise. The mixture was refluxed for 30 minutes and the solvent was substantially distilled off. The crystalline reaction product which separated on cooling was filtered off with suction and recrystallized from n-hexane.

Yield 26 grams melting point 42-43°C Analysis calculated 10.0$ N, 9.8$ Π, C11H12F4N2°2 molecular weight 280 Examp l e 7 A solution of 33.2 grams (0.1.3 mole) of 3-(l 1 ,1 ' ,2·,2'-tetrafluoroethyl)-phenylcarbamic acid chloride in 50 milliliters of absolute benzene was added at 40°C while stirring to a mixture of 8 grams (0.13 mole) of 0,N-dime.thylhydroxyl-amine, 11.3 grams (0.13 mole) of triethylamine and 100 milliliters of absolute benzene. The reaction mixture was maintained for 120 minutes at 40°C. After cooling, the crystalline reaction product was filtered off with suction, washed until the wash water was free from chlorine and re-crystallized from n-hexane.

Yield 30 grams melting point 44-45°C A mixed melting point with the product of Example 6 did not show any depression.

E x am p l e 8 100 Milliliters of methanol and 10 milliliters of NaOH of 33$ strength were added to 26.6 grams (0.1 mole) of N-3-0 ' ,1 ' ,2' ,2,-tetraflu0roethylphenyl)- l-methoxy urea (cf. Example 5). While cooling with icewater and stirring, 1 grams (0.11 mole) of dimethyl sulfate were dropped into ί* the precipitated reaction product was filtered off with suction and washed with water. Finally, it was recrystall-ized from n-hexane .

Yield 24 grams melting point 43-45°C A mixed melting point with the products of Examples 6 and 7 did not show any depression.

B x a m p l e 9 .2 Grams (0.1 mole) of N-3-0 ', 1' ,2' ,2' -tetrafluoroethyl)-phenyl-N' -hydroxy urea, obtained from 3- 1 , 1 ' ,2· ,2·-tetrafluoroethyl) -phenyl isocyanate and hydroxylamine in a manner analogous to that of Example 6, were dissolved in 150 milliliters of methanol. While stirring at 20°C, 25 milliliters of 10 II sodium hydroxide solution and simultaneously 32.5 grams (0.25 mole) of dimethyl sulfate were dropped in at a pH of 9-10. To complete the reaction the reaction mixture was maintained for 1 hour at 20°C. It was then diluted with icewater, the precipitated reaction product was filtered off with suction, washed with water and recrystallized from h-hexane« Yield 25 grams melting point 43-44°C A mixed melting point with the products of Examples 6, 7, and 8 did not show any depression.

E x a m p l e s 1 0 - 2 5 The following compounds were prepared in a manner analogous to that described in the preceding examples: ) N-3-(2' ,2· ^-trichloro-l ' ,1 ' -difluoroethyD-phenyl-ΓΓ· , Ν' -dimethyl urea melting point 164°C 11 ) K-3-(2' ,2'-dichloro-11 ,1 ' ,2' -trifluoroethyl)-phenyl-N' ·, · -dimethyl urea melting point 136-138°C 12) N-3- ' , '-dichloro-2' ,2V,2'-trifluoroethyl)-phenyl-N methyl-N'-methoxy urea melting point 71 -73°C 14 N-3-(2'-chloro-1 ' ,1 » , 2'-trifluoroethyl) -phenyl-N' - methyl-N' -methoxy urea melting point 42-44°C N-3-0 · , 1 ' ,2' ,2» -tetrafluoroethyl) -phenyl-N' ,N»-di- <- methyl urea melting point 121-122°C 16 N-3-(2 · -chloro-1 ·. , 1 ' , 2 ' , 21 -tetrafluoroethyl) -phenyl- » , ^ N' -dimethyl urea melting point 106-108°C 17 N-4-chloro-3-(11 ,1 ' ,2» ,2' -tetrafluoroethyl) -phenyl-N' , ^ N' -dimethyl urea melting point 125-127°C 18 N-4-(2' ,2' ,3' , 3' -tetrafluorocyclobutyl)-phenyl-N' ,Ν'- ί dimethyl urea melting point 1 8-180°C 19 N-4-(2 ' , 21 , 3 ' , 3 ' -tetrafluorocyc'lobutyl) -phenyl-N' -methyl- ^ N ' -methoxy urea melting point 109-112°C N-3-(pentafluoroethyl)-phenyl-N · -methyl urea ^ melting point 119-120°C 21 N-3-(pentafluoroethyl)-phenyl-N' ,Ν' -dimethyl urea melting point 135 C 22 N-3-(pentafluoroethyl) -phenyl-N' -methyl-N1 -methoxy urea V melting point 87-88°C 23 N-3-( 1 ' , 1 ' , 2 · ,3' ,3' ,3' -hexafluoropropyl) -phenyl-N ' - met l-N' -methoxy urea melting point 52-57 C 24 N-3-(heptafluoroisopropyl)-phenyl-N'-,N'-dimethyl urea \s melting point 123°C N-3-(heptafluoroisopropyl)-phenyl-N' -methyl-N' -methoxy ^ urea melting point 49-50°C E x a m p l e 2 6 A wettable powder readily dispersible in water was obtained by mixing 80 parts by weight of N-3- ' , 1 ' ,2' ,2'-tetrafluoroethyl)-phenyl-N' ,Nl-dimethyl urea as active ingredient, 17 parts by weight of precipitated silicic acid as inert substance and 3 parts by weight of sodium oleyl methyl tauride as wetting and dispersing agent, and grinding E x a m p l e 2 7 A dusting powder having good herbicidal properties was obtained by mixing 10 parts by weight of N~3-(1 f , 1 ' -dichloro-2' ,2' ,2'-trifluoroethyl)-phenyl-N' ,Ν' -dimethyl urea as active ingredient and 90 parts by weight of talc as inert substance, and grinding the mixture in a cross beater mill.

E x a m p l e 2 8 An emulsion concentrate was obtained from 15 parts by weight of N-3-0 ' ,1 ' ,2» ,2 ' -tetrafluoroethyD-phenyl-N* ,Ν'-dimethyl urea as active ingredient, 75 parts of cyclohexan-one as solvent and 10 parts by weight of nonyl(ethoxy) ^ phenol as emulsifier.

E x a m p l e 2 9 Numerous weeds and cultivated plants were sown in boxes filled with humus sandy loam and the seeds were covered with soil. On the same day the surface of the soil was sprayed with aqueous suspensions of the following active ingredients: A) N-3-01 ,1 ' -dichloro-2 ■ ,2' ^'-trifluoroethylJ-phenyl-N'- methyl- ' -methoxy urea (cf. Example 12) B) N-3- ' ,1 '-dichloro-^' ,2' ,2 » -trifluoroethyl)-phenyl-N» - ' -dimethyl urea (cf. Example 3) C) N-3-pentafluoroethyl-phenyl-N1 -methyl-N' -methoxy urea (cf. Example 22) As comparative substances the following, chemically closely related compounds were used: 1) N-3-trifluoromethyl-phenyl-N · ,Ν' -dimethyl urea (fluo- meturon) and 2) N-3-trifluoromethyl-phenyl-N'-methyl- l methoxy urea (3-trifluoromethyl-carbanil-N' -methyl-hydroxamic acid th t t 2 a dosage of 0.6 kilogram per hectare is shown in the following table (evaluation 6 weeks after the treatment).

T a b l e 1 type of weed A B c comparative compound 1 2 Sinapia arvensie 100 95 100 100 90 Stollaria media 100 100 100 100 100 Mercurlalis annua 100 100 100 85 50 Viola tricolor 90 100 60 100 '*0 Amaranthus re roflexus 100 100 100 100 95 Portulaca oleracea 100 100 100 100 100 Antheinis arvensis 95 100 100 100 75 Echinochloa ci'us-galli 95 90 75 100 20 Poa annua 100 100 75 100 80 Alopocurue myosuroides 100 95 50 100 60 Eleusine imlica 100 85 95 95 60 average: 98 97 87 The results show that the herbicidal effect of the compounds according to the invention equals or almost equals the effect of comparative compound 1 and is distinctly superior to the effect of comparative compound 2.

It is known that comparative compound 1 (fluometuron) is very effective against annual weeds in cotton cultivations. In other cultivations, however, it cannot be used as it damages the cultivated plants or fully destroys them. fluoreturon and, surprisingly, they damage to a slight extent or even not at all quite a number of other cultivations as shown "by the following Table 2.

T a b l e 2 Tolerability with cultivated plants in an amount of 0.6 kg/ha of active ■ ingredient type of compound comparative compound plant A B C 1 2 cotton good very good very good good very good rice good good very good very bad unsatisfactory carrot very good very good very bad good good soybean very very good very good destroyed good good sunvery very good very good destroyed unsatisfactory good flower The above results show that the compounds according to the invention, with a good herbicidal effect that equals that of comparative compound 1, can be used not only for cotton cultivations but also for a number of other important cultivations. The advantage over comparative compound 2, which also does not much harm to other cultivations, resides in the distinctly better herbicidal effect with the application of the same amounts per unit of area (cf. Table 1).

In the same test series other compounds according to the invention exhibited a broader selectivity than the comparative compound fluometuron, as shown by the following two example s .

E x a m p l e 3 0 D) N-3-pentafluoroethyl-phenyl-lT ,Ν· -dimethyl urea (cf. Example 21); mode of application in accordance with Example 29 T a b l e 5 Herbicidal effect with 0.6 kg/ha of active ingredient - (degree of damage in j>) Sinapis arvcnsia 100 # Stollaria media 100 Kercurialia anrmrc 70 g Viola tricolor 50 i> Amarant us retrofloxus 90 g Portulaca oleracea 100 $> Anthemia arveneio 95 Echinochloa crus-galli 90 $> Poa annua 90 $>■ Alppecurus m osuroides 60 i> Elousine indica 85 1> Average herbicidal effect 85 # The comparative active ingredients 1 and 2 had the following values: 1) 98 2) 70$ T a b l e 4 Tolerabilitv with cultivated plants Type of compound D comparative compounds cultivated plant 1 2 cotton very good good very good maize very good bad very good millet very good bad good rice good very bad unsatisfactory carrot very good very bad good celery very good bad good pea very good bad destroyed white cabbage very good destroyed very bad (planted) On the whole, the herbicidal effect of compound D is meturon. As compared with comparative compound 2, compound D has a distinctly better herbicidal effect.

E x a m p l e ' 3-1 E) N-4-(2' ,2· ,3' ,3'-tetrafluorocyclobutyl)-phenyl-N' ,Ν·- dimethyl urea (cf. Example 18) T a b l e 5 Herbicidal effect with 0.6 kg/ha of active ingredient - (degree of damage in ) Sinapis arvensis 100 * Stellaria media 100 * Mercurialis annua 75 * Viola tricolor 5 * Amaranthue retroflexus 100 Portulaca oleracea 100 * An hemiβ arvensis 100 Echinochloa crus-galli 100 Poa annua 100 * Alopecurus myoauroides 100 1° Eleusine indica 95 Average herbicidal effect 94 o Comparative compound 1 98 io 70 # Comparative compound 2 a b l e 6 Tolerability with cultivated plants type of compound E comparative compounds cultivated plant ■ 1 2 cotton very good good very good celery very good bad good pea good bad destroyed The herbicidal effect of compound E according to the invention is much better than that of comparative compound 2 and approximately equal to that of comparative compound f i "bility of application.

E x a m p l e 3 2 In a further test, weeds and cultivated plants were sown as described in Example 29. In this test the active ingredients were mixed with the soil used for covering the seeds, in an amount corresponding to 0.5 kilogram of active ingredient per hectare. The following compounds were tested against fluometuron as comparative compound: P) N-3-0 · ,1 · ,2' ^'-tetrafluoroeth D-phenyl-N'-methyl-N'- methoxy urea (cf. Examples 6-8) G) IT-3-(2»-chloro-1 ' ,1 ' ,2 ' -trifluoroethyl)-phenyl-N' ,Ν'- dimethyl urea (cf. Example 13) weeks after the treatment the compounds exhibited the following herbicidal effect (degree of damage in ) : T a b l e 7 Herbicidal effect (degree of damage in type of weed compounds comparative compound P Or Sinapis arvensis 100 90 100 Echlnochloa crua-galli 70 100 90 Poa annua 90 85 100 Stellarla media 100 100 100 A themis ar ensis 100 100 100 Amaranthus retroflexus 100 95 100 Chenopodium album 100 100 95 Average : ^ 96 98 The herbicidal effect of the active ingredients according to the invention was approximately equal to that of the comparative compound. The following table demonstrates the T a b 1 e 8 Type of compounds comparative cultivated compound plant P G cotton very good very good good kidney bean good good unsatisfactory soybean very £OOd good destroyed horse bean good good destroyed carrot very good very good very bad maize good very good bad millet good good bad oat good good destroyed rice very good good very bad sunflower good very good destroyed The table shows that the compounds according to the invention can be used in a much broader field of application than the comparative compound.

E x a m p l e 3 3 H) N-3- · ,1 ' ,2»-trifluoro-2'-chloroethyl)-phenyl-Er'- methyl-N' -methoxy urea (cf. Example 14) Mode of application as described in Example 32 weeks after the treatment the compound had the following herbicidal effect: T a b l e 9 Herbicidal effect (degree of damage in $) Sinapis arvensis 95$ Echinochloa crus-galli 100$ Poa annua 95$ Stellaria media 100$ Anthemis arvensis 100$ (Table 9, cont.) Average 97 Comparative compound 98$ (cf. Table T a b l e 1 0 Tolerability with cultivated plants type of compound H comparative cultivated compound plant cotton very good good kidney bean very good unsatisfactory pea good bad celery very good bad With an approximately equal herbicidal effect, the compound of the invention is distinctly ιsuperior to fluometuron owing to its sparing properties not only with respect to cotton but also with respect to other cultivated plants.

E x a m p l e 3 4 I) N-3- ' ,1 ' ,2' ,2'-tetrafluoroethyl)' -phenyl-N' ,Ν' -dimethyl urea (cf. Example 15); mode of application according to Example 32.

T a b l e 1 1 Herbicidal effect with 0.6 kg/ha (degree of damage in Sinapifs arvensis 100 $> Echinochloa crus-palli 100 £ Poa annua 100 i» Stellax-ia media 100 $>' Anthomis arvensis 100 £ A.ma ranthus rotroflexua 100 $> Chenopodium album 90 Average 99 i> Comparative compound SSjo (cf. Table 7) t T a b l e 1 2 Tolerability with cultivated plants type of compound I comparative cultivated compound plant cotton good good celery good bad carrot good very bad . maize good bad millet good bad ..

The table shows that this compound according to the invention is also superior to the comparative compound with respect to its tolerability with cultivated plants. Hence, it follows that it can be used in a broader field of application. The herbicidal effects of the two compounds are approximately identical.

The examples demonstrate that all compounds according to the invention, the biological activity of which had been ascertained by tests, have a good herbicidal effect and do not damage a great number of cultivated plants, so that they can be used in a much wider field of application.

Claims (1)

1. IS IS Compounds of the general formula which represents of 2 to carbon atoms or cycloalkyl of 3 to carbon atoms and which substituted by to 7 halogen at least 2 of which are fluorine atoms represents hydrogen or chlorine and represents methyl or luoromethy luoroethyl methyl oethyl A herbicidal preparation which com rises as active ingredient a compound as claimed In Claim together with a wetting or dispersing an a liquid or solid a grinding a granulating agent and optionally a further biocidal agent or a A method for controlling the growth of undesired plants which comprises using a preparation as claimed in Claim 22 in a concentration of the active ingredient which is sufficient to destroy the plants and does no harm to the cultivated process for manufacture of compounds of the in which B represents an alkyl of 2 to carbon atoms or cycloalkyl of to carbon atoms which are substituted by to 7 halogen at least 2 of which fluorine represents hydrogen or chlorine and represents methyl or which comprises reacting correspondingly substituted isocyanates or acid chlorides with or or with 0 or amine with subsequent alkylation of the ion product or hydroxylamine with subsequent dialkylation of the reaction or methyl isocyanate or acid chloride or or acid phenyl COHEN ZEDE SPISBACH Box Attorneys for Applicant insufficientOCRQuality