N-Phenyl-N-pyrimidin-2-yl-ureas with herbicidal and plant-growth regulating activity.

0001The present invention relates to new N-phenyl-N-pyrimidin-2-yl ureas with herbicidal and plant growth-regulating action, agrochemical compositions which contain these substances as active compounds, the use of the new ureas for combating weeds or for regulating plant growth, and processes to make the new connections. The invention also relates to new intermediates and processes for their production.

0002(Pyrimidin-2-yl) -2-nitroanilines have become known from the patent specification DD-151 404 and the European patent application EP-A-0 172 786. These compounds are fungicidally active. In contrast, it was surprisingly found that N-phenyl-N-pyrimidin-2-yl-ureas have herbicidal or plant growth regulatory activity.

0003The invention relates to ureas of the formula I.<chemistry id="chem0001" num="0001"><img file="EP0337943A2_D0001.tif" /></chemistry>wherein<ul id="ul0001" list-style="none"><li>R¹, R², and R³ independently of one another hydrogen; Halogen; C.₁-C₄-Alkyl; C.₁-C₄-Alkoxy; C.₁-C₄Haloalkyl; Ci-C₄-Haloalkoxy; C.₁-C₄-Alkyl-S (O)_n-; Nitro; Cyano; C.₁-C₄-Alkoxycarbonyl; di- (Ci-C₄Alkylamino) carbonyl; mono- (C₁-C₄Alkylamino) carbonyl; Carbamoyl; Ci-C₄-Halogenalkyl-S (O) n-; C.₁-C₄-Alkylcarbonyl; or -PO [O- (C₁-C₄) Alkyl]₂;</li><li>R⁴ Ci-Cs-alkyl; Ci-C4 alkoxy; C.₁-C₄-Alkyl-S (O)_n-; C.₁-C₄Haloalkyl; C.₁-C₄-Haloalkoxy; unsubstituted, or up to three times the same or different by halogen, Ci-C₄-Alkyl, Ci-C4-haloalkyl or Ci-C₄-Alkoxy substituted phenyl; 2-furanyl; 2-thienyl; 3-thienyl; unsubstituted or up to three times the same or different by Ci-C₄Alkyl substituted C₃-Cs cycloalkyl; Cyano; C.₂-C₄Haloalkenyl;</li><li>Ci-C₄-Alkoxy-Ci-C₄-alkyl; C._i-C₄-Alkoxy-Ci-C₄-alkoxy; or halogen-Ci-C₄-alkylthio;</li><li>R⁵ Hydrogen; C.₁-C₃-Alkyl; C._i-C₃Haloalkyl; Halogen; or Ci-C₃-Haloalkoxy; and</li><li>n 0, 1 or 2</li></ul>means with the proviso that if one of the radicals R¹, R² or R³ Nitro means that this substituent must not be bound in the 2- or 6-position of the phenyl ring, and salts and addition compounds of the compounds of the formula I with acids, bases and complexing agents.

0004Within the scope of the invention disclosed here, the generic terms given include, for example, the following specific individual substituents, this list not being a limitation of the invention:<ul id="ul0002" list-style="none"><li>Alkyl includes the straight-chain or branched C₁-C₆-Alkyls, such as methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, tert-butyl, iso-butyl, the isomeric pentyls - such as n-pentyl, tert-pentyl (1,1- Dimethylpropyl), iso-pentyl (1-ethylpropyl), and the isomeric hexyl radicals. The Ci-Cs-alkyl radicals are preferred.</li></ul>

0005Halogen is fluorine, chlorine, bromine and iodine. Fluorine, chlorine and bromine are preferred.

0006Haloalkyl means the completely or partially identical or different halogen-substituted alkyls, according to the respective definition, such as trifluoromethyl, difluoromethyl, 1,1,2,2-tetrafluoroethyl, 2-chloroethyl, pentafluoroethyl, chloridifluoromethyl, dichloromethyl, chlorofluoromethyl, 1.1 -Dichloro-2,2,2-trifluoroethyl, 1,1-dichloroethyl or heptafluoropropyl.

0007As Ci-C₄Alkoxycarbonyl radicals include methoxycarbonyl, ethoxy carbonyl and the isomeric propyloxycarbonyls and butyloxycarbonyls.

0008Alkoxy are within the scope of the respective definition of the isomeric alkyloxy radicals, primarily methoxy, ethoxy, (i) -propyloxy, (n) -propyloxy, (i) -butyloxy, (t) -butyloxy, (n) -butyloxy and (sec ) Butyloxy.

0009Haloalkoxy and haloalkylthio are within the scope of the respective definition, the isomeric one or more identical or different halogen-substituted alkyl radicals, such as trifluoromethoxy, 2,2,2-trifluoroethoxy, trifluoromethylthio, 2,2,3,3,3-pentafluoropropyloxy or 1,1 , 2,2-tetrafluoroethoxy, difluoromethoxy or 2-chloroethoxy.

0010Examples of alkoxyalkyl radicals include: 2-ethoxyethyl, 2-methoxyethyl, 3-methoxypropyl, 2-methoxy-1-methylethyl and methoxymethyl.

0011Group C₁-C₄-Alkyl-S (O)_n- stands for the respective alkylthio, alkylsulfinyl and alkylsulfonyl radicals. Methylthio, methylsulfinyl and methylsulfonyl are particularly preferred.

0012From the group PO [O (C₁-C₄) Alkyl]₂ are PO (OCH₃)₂, and PO (OC₂H₅)₂ prefers.

0013di- (Ci-C4-Alkylamino) carbonyl includes both those with the same or different C₁-C₄-Alkyl radicals substituted radicals.

0014Haloalkylthio is in particular fluoromethylthio, difluoromethylthio, trifluoromethylthio, 1,1,2,2-tetrafluoroethylthio, chlorodifluoromethylthio and dichlorofluoromethylthio.

0015In the other substituents, which are composed of several basic elements, the partial elements can be freely selected within the definition and have the above meaning.

0016In the 4-position of the phenyl ring, unsubstituted compounds of the formula I should be emphasized<chemistry id="chem0002" num="0002"><img file="EP0337943A2_D0002.tif" /></chemistry>wherein<ul id="ul0003" list-style="none"><li>R¹ Halogen; Cyano; C.₁-C₄-Alkoxy; C.₁-C₄-Haloalkoxy; C.₁-C₄-AlkYl-S (O)_n-; C.₁-C₄-Alkyl; C.₁-C₄Haloalkyl; Ci-C₄-Alkoxycarbonyl; di- (Ci-C₄Alkylamino) carbonyl; mono- (Ci-C₄Alkylamino) carbonyl; Carbamoyl; Ci-C₄-Halogenalkyl-S (O) n-; or -PO [O- (Ci-C₄) Alkyl]₂;</li><li>R² Hydrogen; Halogen; Cyano; Nitro; C.₁-C₄-Alkyl; C.₁-C₄-Alkoxy; C.₁-C₄Haloalkyl; C.₁-C₄-Alkoxycarbonyl; or C₁-C₄-Alkylcarbonyl;</li><li>R³ Hydrogen; Halogen; or C₁-C₄-Alkyl means and n and the radicals R⁴ and R⁵ are as previously defined.</li></ul>

0017Preferred subgroups are those compounds of the formula in which<ul id="ul0004" list-style="none"><li>a) the rest R¹ is attached to the 2-position of the phenyl ring,</li><li>b) the rest R² is bound to the 3-position of the phenyl ring,</li><li>c) the rest R³ is attached to the 5-position of the phenyl ring,</li><li>d) the rest R² is bound to the 6-position of the phenyl ring,</li><li>e) the rest R¹ is bound to the 3-position of the phenyl ring,</li><li>f) the rest R³ is bound to the 3-position of the phenyl ring,</li><li>g) the rest R² is bound to the 5-position of the phenyl ring.</li></ul>

0018The following combinations of subgroups should be emphasized: a + b, a + g, a + d, e + g, e + d, a + b + c, a + f + d, a + c + d and e + c + d , with the combination of only two subgroups the radical R³ stands for hydrogen.

0019Particularly noteworthy are compounds of the formula I in which<ul id="ul0005" list-style="none"><li>R¹ Halogen; Cyano; C.₁-C₃-Alkoxy; Ci-C₂-Haloalkoxy; Methyl-S (O)_n-; Ci-C₃-Alkyl; C.₁-C₂Haloalkyl; Ci-C₄-Alkoxycarbonyl; Carbamoyl; Difluoromethylthio or -PO [O- (C₁-C₂) Alkyl]₂;</li><li>R² Hydrogen; Fluorine; Chlorine; Bromine; Cyano; Nitro; C._i-C₃-Alkyl; C.₁-C₂Haloalkyl; or Ci-C3-alkoxycarbonyl;</li><li>R³ Hydrogen; Chlorine; Fluorine; or C₁-C₃-Alkyl;</li><li>R⁴ C.₁-C5 alkyl; C.₁-C₄-Alkoxy; Ci-C4-alkylthio; Cyclopropyl; Phenyl; Furan-2-yl; Thiophene-2-yl; Cyano; C.₁-C₃-Haloalkoxy; Ci-C₂-Alkoxy-Ci-C₂-alkyl; Ci-C₂-Alkoxy-Ci-C2-alkoxy; Methylsulfinyl; Methylsulfonyl; or C₂-C₃Haloalkenyl;</li><li>R⁵ C.₁-C₃-Alkyl; Fluorine; Chlorine; Bromine; C.₁-C₃Haloalkyl; or C₁-C₃-Haloalkoxy; and</li><li>n 0, 1 or 2</li></ul>means.

0020Compounds of the formula I in which<ul id="ul0006" list-style="none"><li>R¹ Halogen; Methyl; Trifluoromethyl; Trifluoromethoxy; Difluoromethoxy; C.₁-C₃-Alkoxy; Methylthio; Methylsulfinyl; Methylsulfonyl; Cyano; C.₁-C₄-Alkoxycarbonyl; Carbamoyl; Difluoromethylthio; or -PO (OC₂H₅)₂;</li><li>R² Hydrogen; Fluorine; Chlorine; Bromine; Nitro; Ethyl; Methyl; Trifluoromethyl; Methoxy; or C₁-C₃-Alkoxycarbonyl;</li><li>R³ Hydrogen; Chlorine; or methyl;</li><li>R⁴ C.₁-C₅-Alkyl; Ci-C₄-Alkoxy; Ci-C₄-Alkyl thio; Cyclopropyl; Phenyl; Furan-2-yl; Thiophene-2-yl; Cyano; 1,1,2,2-tetrafluoroethoxy; 2-chloroethoxy; Methoxymethyl; 2-methoxy-ethoxy; Methylsulfinyl; Methylsulfonyl; or 2,2-dichlorovinyl;</li><li>R⁵ C.₁-C₃-Alkyl; Fluorine; Chlorine; Bromine; Difluoromethoxy; Trifluoromethyl; Pentafluoroethyl; Chlorodifluoromethyl; Difluoromethyl; Dichloromethyl; Chlorofluoromethyl; 1,1-dichloro-2,2,2-trifluoroethyl; 1,1-dichloroethyl; or heptafluoropropyl;</li></ul>means.

0021In particular, the invention relates to compounds of the formula I in which<ul id="ul0007" list-style="none"><li>R¹ Fluorine; Chlorine; Bromine; Iodine; Trifluoromethyl; Methyl; Difluoromethoxy; Methoxy; Methylthio; PO (OC₂H₅)₂; Methoxycarbonyl; Methylsulfonyl; or cyano;</li><li>R² Hydrogen; Fluorine; Chlorine; Bromine; Nitro; Methyl; Ethyl; Trifluoromethyl; or methoxycarbonyl;</li><li>R³ Hydrogen; or methyl;</li><li>R⁴ C.₁-C₅-Alkyl; Butylthio; Thiophene-2-yl; Furan-2-yl; C.₁-C₄-Alkoxy; Methylthio; Methylsulfinyl; Methylsulfonyl; or cyclopropyl; and</li><li>R⁵ Methyl; Chlorine; Dichloromethyl; Pentafluoroethyl; Difluoromethyl; Chlorofluoromethyl; Trifluoromethyl; or chlorodifluoromethyl</li></ul>means.

0022Also to be emphasized are the compounds of the formula in which<ul id="ul0008" list-style="none"><li><ul id="ul0009" list-style="none"><li>a) R¹ fluorine, chlorine, bromine, trifluoromethyl, cyano, difluoromethyl, trifluoromethoxy, methyl or methoxy bonded in position 2 of the phenyl ring,</li><li>R² and R³ Hydrogen,</li><li>R⁴ Methyl, furan-2-yl or cyclopropyl, and</li><li>R⁵ Chlorine, methyl, trifluoromethyl or chlorodifluoromethyl, or</li></ul></li><li><ul id="ul0010" list-style="none"><li>b) R¹ fluorine, chlorine, bromine, trifluoromethyl, difluoromethoxy, trifluoromethoxy, cyano or methoxy bonded in position 2 of the phenyl ring,</li><li>R² fluorine or chlorine bonded in position 3 or 6 of the phenyl ring,</li><li>R⁴ Methyl, furan-2-yl or cyclopropyl, and</li><li>R⁵ Chlorine, methyl, trifluoromethyl or chlorodifluoromethyl, or</li></ul></li><li>c) R¹ chlorine bound in position 3 of the phenyl ring,<ul id="ul0011" list-style="none"><li>R² chlorine bound in position 5 of the phenyl ring,</li><li>R⁴ Methyl, furan-2-yl or cyclopropyl, and</li><li>R⁵ Chlorine, methyl trifluoromethyl or chlorodifluoromethyl means.</li></ul></li></ul>

0023Due to their herbicidal effects, the following should be mentioned:<ul id="ul0012" list-style="none"><li>N- (2-bromophenyl) -N- (4-chloro-6-methyl-pyrimidin-2-yl) urea,</li><li>N- (4-methyl-6-trifluoromethyl-pyrimidin-2-yl) -N- (2-trifluoromethyl-phenyl) urea,</li><li>N- (2,3-dichlorophenyl) -N- (4-methyl-6-trifluoromethyl-pyrimidin-2-yl) urea,</li><li>N- (2,5-dichlorophenyl) -N- (4,6-dimethyl-pyrimidin-2-yl) urea,</li><li>N- (4-chloro-6-methyl-pyrimidin-2-yl) -N- (2,5-dichlorophenyl) urea,</li><li>N- (2,5-dichlorophenyl) -N- (4-methyl-6-trifluoromethyl-pyrimidin-2-yl) urea,</li><li>N- [4- (chlorodifluoromethyl) -6-methyl-pyrimidin-2-yl] -N- (2,5-dichlorophenyl) urea,</li><li>N- (4-chloro-6-methyl-pyrimidin-2-yl) -N- (2,6-dichlorophenyl) urea,</li><li>N- (2,6-dichlorophenyl) -N- (4-methyl-6-trifluoromethyl-pyrimidin-2-yl) urea,</li><li>N- (4-cyclopropyl-6-trifluoromethyl-pyrimidin-2-yl) -N- (2,6-dichlorophenyl) urea,</li><li>N- (3,5-dichlorophenyl) -N- (4-methyl-6-trifluoromethyl-pyrimidin-2-yl) urea,</li><li>N- (5-chloro-2-methylphenyl) -N- (4-chloro-6-methyl-pyrimidin-2-yl) urea,</li><li>N- (5-chloro-2-methoxyphenyl) -N- (4-methyl-6-trifluoromethyl-pyrimidin-2-yl) urea,</li><li>N- (2-iodophenyl) -N- (4-methyl-6-trifluoromethyl-pyrimidin-2-yl) urea,</li><li>N- (2-chloro-6-methylphenyl) -N- (4-chloro-6-methylpyrimidin-2-yl) urea,</li><li>N- (3-chloro-2-methoxyphenyl) -N- (4-methyl-6-trifluoromethylpyrimidin-2-yl) urea,</li><li>N- (2,6-difluorophenyl) -N- (4-methyl-6-trifluoromethylpyrimidin-2-yl) urea,</li><li>N- (2,5-difluorophenyl) -N- (4-methyl-6-trifluoromethyl-pyrimidin-2-yl) urea,</li><li>N- (2-cyanophenyl) -N- (4-methyl-6-trifluoromethyl-pyrimidin-2-yl) urea,</li><li>N- (2-bromophenyl) -N- (4-cyclopropyl-6-trifluoromethyl-pyrimidin-2-yl) urea,</li><li>N- (4-isopropyl-6-trifluoromethyl-pyrimidin-2-yl) -N-2- (trifluoromethylphenyl) urea,</li><li>N- (2-fluorophenyl) -N- (4-methyl-6-trifluoromethyl-pyrimidin-2-yl) urea,</li><li>N- (2-fluorophenyl) -N- (4-isopropyl-6-trifluoromethyl-pyrimidin-2-yl) urea,</li><li>N- (2,5-dichlorophenyl) -N- (4-ethyl-6-trifluoromethyl-pyrimidin-2-yl) urea,</li><li>N- (2,6-dichlorophenyl) -N- (4-difluoromethyl-6-methyl-pyrimidin-2-yl) urea,</li><li>N- (2,6-dichlorophenyl) -N- (4-methylthio-6-trifluoromethyl-pyrimidin-2-yl) urea,</li><li>N- (2,6-dichloro-3-methyl) -N- (4-methyl-6-trifluoromethyl-pyrimidin-2-yl) urea,</li><li>N- (2,6-dichloro-3-methylphenyl) -N- (4-isopropyl-6-trifluoromethyl-pyrimidin-2-yl) urea,</li><li>N- (2-chloro-6-trifluoromethyl-phenyl) -N- (4-methyl-6-trifluoromethyl-pyrimidin-2-yl) urea,</li><li>N- (2-chloro-6-methylphenyl) -N- (4-methyl-6-trifluoromethyl-pyrimidin-2-yl) urea,</li><li>N- (2-methyl-6-tr'rfluoromethylphenyl) -N- (4-methyl-6-tr'rfluoromethyl-pyrimidin-2-yl) urea,</li><li>N- (5-chloro-2-difluoromethoxyphenyl) -N- (4-methyl-6-trifluoromethyl-pyrimidin-2-y1) urea,</li><li>N- (2-methylthiophenyl) -N- (4-methyl-6-trifluoromethyl-pyrimidin-2-yl) urea,</li><li>N- (4-cyclopropyl-6-trifluoromethyl-pyrimidin-2-yl) -N- (2,5-difluorophenyl) urea,</li><li>N- (2,6-difluorophenyl) -N- (4-ethyl-6-trifluoromethyl-pyrimidin-2-yl) urea,</li><li>N- (6-chloro-2-fluorophenyl) -N- (4-methyl-6-trifluoromethyl-pyrimidin-2-yl) urea,</li><li>N- (6-chloro-2-fluorophenyl) -N- (4-cyclopropyl-6-trifluoromethyl-pyrimidin-2-yl) urea,</li><li>N- (2-difluoromethoxyphenyl) -N- (4-methyl-6-trifluoromethyl-pyrimidin-2-yl) urea,</li><li>N- (6-chloro-2-methoxycarbonyl-phenyl) -N- (4-methyl-6-trifluoromethyl-pyrimidin-2-yl) urea,</li><li>N- (2-bromophenyl) -N- [4- (furan-2-yl) -6-trifluoromethyl-pyrimidin-2-yl] urea,</li><li>N- (2-chloro-6-methylphenyl) -N- (4-methoxymethyl-6-trifluoromethyl-pyrimidin-2-yl) urea, and</li><li>N- (2-difluoromethoxy-6-methyl-phenyl) -N- (4-methyl-6-trifluoromethyl-pyrimidin-2-yl) urea.</li></ul>

0024The compounds of the formula can be prepared by<ul id="ul0013" list-style="none"><li>a) reacting an aniline of formula II with phosgene to a carbamine chloride of formula III and this in a second step with NH₃ to<chemistry id="chem0003" num="0003"><img file="EP0337943A2_D0003.tif" /></chemistry>reacting with a urea of ​​the formula or</li><li>b) an aniline of the formula II is reacted with halosulfonyl isocyanate IX to give a halosulfonylurea of ​​the formula IV<chemistry id="chem0004" num="0004"><img file="EP0337943A2_D0004.tif" /></chemistry>and hydrolyzed this in a second stage or directly to a compound of the formula I, where Y represents a group which can be split off under the reaction conditions, such as halogen, preferably chlorine.</li></ul>

0025The reactions II → III, III → I and IV → I proceeding with elimination of hydrogen halide or HY elimination are preferably carried out using acid-binding agents (bases).

0026Organic or inorganic bases are suitable as such, for example tertiary amines such as trialkylamines (trimethylamine, triethylamine, tripropylamine etc.), pyridines (pyridine, 4-dimethylaminopyridine, 4-pyrrolidylaminopyridine etc.), alcoholates such as potassium tert-butoxide, Sodium methylate or ethylate. The aforementioned reactions as well as the reaction VII → II - described later - can also be carried out under phase transfer conditions with bases according to methods known per se (Lit. Dehmlow &amp; Dehmlow, Phase Transfer Catalysis Verlag Chemie, Weinheim, 1983).

0027In the case of process variants a) and b), one or more inert solvents or diluents may be present, unless expressly specified in detail. For example, aliphatic and aromatic hydrocarbons such as benzene, toluene, xylenes, petroleum ether; halogenated hydrocarbons such as chlorobenzene, methylene chloride, ethylene chloride, chloroform, carbon tetrachloride, tetrachlorethylene; Ethers and ethereal compounds such as dialkyl ether (diethyl ether, diisopropyl ether, tert-butyl methyl ether, etc.), anisole, dioxane, tetrahydrofuran; Nitriles such as acetonitrile, propionitrile; N, N-dialkylated amides such as dimethylformamide; Dimethyl sulfoxide; Ketones such as acetone, diethyl ketone, methyl ethyl ketone and mixtures of such solvents with one another.

0028The anilines of the formula II, like the carbamoyl chlorides of the formula III and the ureas of the formula IV, are valuable intermediates. The carbamoyl chlorides III and the ureas IV are new, while some of the compounds of the formula II are known from DD-B-151 404.

0029The invention thus also relates to the new compounds of the formula II<chemistry id="chem0005" num="0005"><img file="EP0337943A2_D0005.tif" /></chemistry>wherein<ul id="ul0014" list-style="none"><li>R¹ Halogen; Cyano; Ci-C₄-Alkoxy; C._i-C₄-Haloalkoxy; Ci-C₄-Alkyl-S (O)_n-; Ci-C4-alkyl; C.₁-C₄Haloalkyl; Ci-C₄-Alkoxycarbonyl; di- (Ci-C₄Alkylamino) carbonyl; mono- (C_i-C₄Alkylamino) carbonyl; Carbamoyl; 6</li><li>C.₁-C₄Haloalkyl-S (O)_n-; or -PO [O- (C₁-C₄) Alkyl]₂;</li><li>R² Hydrogen; Halogen; Cyano; Nitro; C._i-C₄-Alkyl; C._i-C₄-Alkoxy; Ci-C₄Haloalkyl; C.₁-C₄-Alkoxycarbonyl; or Ci-C₄-Alkylcarbonyl;</li><li>R³ Hydrogen; Halogen; or C₁-C₄-Alkyl;</li><li>R⁴ C.₁-C₆-Alkyl; Ci-C4 alkoxy; C.₁-C₄-Alkyl-S (O)_n-; Ci-C₄Haloalkyl; C.₁-C₄-Haloalkoxy; unsubstituted, or up to three times the same or different by halogen, C₁-C₄-Alkyl, Ci-C4-haloalkyl or Ci-C₄-Alkoxy substituted phenyl; 2-furanyl; 2-thienyl; 3-thienyl; unsubstituted or up to three times the same or different by C₁-C₄Alkyl substituted C₃-C₆Cycloalkyl; Cyano; C.₂-C₄Haloalkenyl; Ci-C₄-Alkoxy-Ci-C₄-alkyl; Ci-C₄-Alkoxy-Ci-C₄-alkoxy; or halogen-Ci-C4-alkylthio;</li><li>R⁵ Hydrogen; C.₁-C₃-Alkyl; C.₁-C₃Haloalkyl; Halogen; or Ci-C₃-Haloalkoxy; and</li><li>n 0, 1 or 2</li></ul>means with the proviso that a) if one of the radicals R² or R³ Nitro means that this substituent must not be bound in the 2- or 6-position of the phenyl ring and if the radicals R⁴ and R⁵ R stands for methyl¹ does not represent chlorine, methoxy, ethoxy, fluorine, iodine, methyl or bromine and that the following individual compounds are not included:<ul id="ul0015" list-style="none"><li>N - [(4,6-bis-trifluoromethyl) pyrimidin-2-yl] -2,6-dichloroaniline and N- (4-chloro-6-methylpyrimidin-2-yl) -3-chloroaniline.</li></ul>

0030The invention also relates to new N, N-disubstituted carbamoyl chlorides of the formula III<chemistry id="chem0006" num="0006"><img file="EP0337943A2_D0006.tif" /></chemistry><ul id="ul0016" list-style="none"><li>where the radicals R¹ to R⁵ as defined in Formula I and new ureas of Formula IV<chemistry id="chem0007" num="0007"><img file="EP0337943A2_D0007.tif" /></chemistry></li><li>where R¹ to R⁵ are as defined under formula and Y is halogen, C₁-C₄-Alkoxy or phenoxy means.</li></ul>

0031The compounds of formula III and IV are intermediates of processes a) and b) and can be prepared from the corresponding anilines of formula II as described there.

0032The new anilines of the formula can be prepared analogously to processes known from the literature, for example by:<ul id="ul0017" list-style="none"><li>aa) reaction of guanidines of the formula V with 1,3-dicarbonyl compounds of the formula VI<chemistry id="chem0008" num="0008"><img file="EP0337943A2_D0008.tif" /></chemistry>the condensation reaction being carried out, if desired, in the presence of water-binding agents (lit .: DJ Brown in "The Chemistry of Heterocyclic Compounds" Vol. VI 1962, Interscience Publ. New York; J. Am. Chem. Soc. 69 1819 (1947); J. Am. Chem. Soc. 72 2948 (1950); J. Org. Chem. 291439 (1964) or J. Org. Chem. 291883 (1964), Houben-Weyl "Methods of Organic Chemistry Vol. VIII pp. 180ff ) or</li><li>bb) by reacting an aniline of formula VII with a pyrimidine of formula VIII under the action of a base<chemistry id="chem0009" num="0009"><img file="EP0337943A2_D0009.tif" /></chemistry>where the radicals R¹ to R⁵ are previously defined and X for a nucleofugic group such as halogen, C₁-C₄Alkylsulfonyl or phenylsulfonyl.</li></ul>

0033Suitable bases for carrying out this process include potassium, tert-butoxide, Na₂CO₃; K₂CO₃ or NaH.

0034These processes are generally available for the synthesis of compounds of the formula II and are applicable to all starting materials of the formulas V, VI, VII and VIII (in which the radicals R¹ to R⁵ is defined in the scope of the formula of compounds I).

0035The invention further relates to herbicidal and plant growth regulating compositions comprising a compound of the formula together with suitable auxiliaries and / or carriers.

0036The active compounds of formula 1 are generally successfully used at application rates of 0.005 to 5 kg / ha, in particular 0.1 to 3 kg / ha. The dosage required for the desired effect can be determined by experiment. It depends on the type of action, the stage of development of the crop and weed, and on the application (place, time, method) and, depending on these parameters, can vary within wide ranges.

0037At lower application rates, the compounds of formula 1 are distinguished by growth-inhibiting and herbicidal properties which make them excellent for use in crops of useful plants, in particular in cereals, cotton, soybeans, sunflowers, rapeseed, maize and rice.

0038The compounds of formula I also have plant growth regulatory properties. Both monocots and dicots are influenced in their growth. An inhibition of vegetative growth allows a denser cultivation of the crop in many crop plants, so that an additional yield, based on the soil area, can be achieved. Another mechanism of increasing yield with growth regulators is based on the fact that the nutrients benefit flower and fruit formation to a greater extent, while vegetative growth is restricted. When larger amounts are applied, weeds and grasses are damaged in their development so that they die.

0039The growth-regulating compounds of the formula can be used in a particularly advantageous manner for regulating the growth of undersown seeds in maize crops. In principle, those plants that cover the soil between the individual maize plants and thus primarily counter soil erosion in maize crops are suitable as undersown in maize crops. Suitable plants for undersowing include rapeseed, clover, grass or legumes.

0040The compounds of the formula inhibit the new growth of grasses at suitable application rates. In lawn crops (parks, gardens, etc.), this allows the number of cuts required to be reduced or the periods between cuts to be extended. In a particularly advantageous manner, granule formulations of the active compounds of the formula I can be used. The granules can either contain the active ingredient alone, in addition to the usual auxiliaries and carriers, or the active ingredient is formulated as granules together with a mineral fertilizer and / or optionally further active ingredients for controlling moss or other plant growth which is undesirable in lawn crops. The use as a scattering granulate allows, with the help of the processing equipment common in lawn crops, to inhibit the new growth of the grasses for a long time. The granulate can be produced in a manner known per se, it preferably has a grain size of 0.1 to 2.0 mm, in particular of 0.25 to 1.0 mm.

0041The invention also relates to herbicidal and plant growth regulating compositions which comprise an active ingredient of the formula I, and to processes for pre- and post-emergent weed control and for influencing plant growth in monocotyledonous and dicotyledonous plants, in particular grasses, tropical soil coverers and poultry shoots.

0042The compounds of formula 1 are used in unchanged form or preferably as agents together with the auxiliaries customary in formulation technology and are therefore, for example, emulsion concentrates, directly sprayable or dilutable solutions, diluted emulsions, wettable powders, soluble powders, dusts, granules, and also encapsulations in eg polymeric materials processed in a known manner. The methods of application such as spraying, atomizing, dusting, scattering or pouring are chosen in the same way as the type of agent, in accordance with the intended goals and the prevailing conditions. The active substances of the formula can also be applied (pickled) to mineral fertilizers. The agent obtainable in this way is advantageously suitable as a growth regulator in grasses. The wording, ie The agents, preparations or compositions containing the active ingredient of formula 1 and optionally a solid or liquid additive are prepared in a known manner, for example by intimately mixing and / or grinding the active ingredients with extenders, such as with solvents, solid carriers, and optionally surface-active compounds (Surfactants).

0043Possible solvents are: aromatic hydrocarbons, preferably fractions C₈ to C₁₂, such as Xylene mixtures or substituted naphthalenes, phthalic esters such as dibutyl or dioctyl phthalate, aliphatic hydrocarbons such as cyclohexane or paraffins, alcohols and glycols and their ethers and esters such as ethanol, ethylene glycol, ethylene glycol monomethyl or ethyl ether, ketones such as cyclohexanone, strongly polar solvents such as N-methyl -2-pyrrolidone, dimethyl sulfoxide or dimethylformamide, and optionally epoxidized vegetable oils, such as epoxidized coconut oil or soybean oil; or water. Natural rock flours, such as calcite, talc, kaolin, montmorillonite or attapulgite, are generally used as solid carriers, for example for dusts and dispersible powders. To improve the physical properties, highly disperse silica or highly disperse absorbent polymers can also be added. Porous types such as, for example, come as granular, adsorptive granulate carriers Pumice stone, broken brick, sepiolite or bentonite, as non-sorptive carrier materials, for example calcite or sand. In addition, a large number of pregranulated materials of an inorganic or organic nature, such as, in particular, dolomite or comminuted plant residues can be used.

0044Depending on the nature of the active ingredient of the formula I to be formulated, suitable surface-active compounds are nonionic, cationic and / or anionic surfactants with good emulsifying, dispersing and wetting properties. Surfactants are also to be understood as mixtures of surfactants.

0045Suitable anionic surfactants can be both so-called water-soluble soaps and water-soluble synthetic surface-active compounds.

0046The soaps are the alkali, alkaline earth or optionally substituted ammonium salts of higher fatty acids (C_iα-C₂₂), such as the Na or K salts of oleic or stearic acid, or of natural fatty acid mixtures which can be obtained, for example, from coconut or tallow oil. The fatty acid methyl taurine salts should also be mentioned.

0047However, so-called synthetic surfactants are used more frequently, in particular fatty sulfonates, fatty sulfates, sulfonated benzimidazole derivatives or alkylarylsulfonates.

0048The fatty sulfonates or sulfates are generally present as alkali, alkaline earth or optionally substituted ammonium salts and have an alkyl radical with 8 to 22 carbon atoms, alkyl also including the alkyl part of acyl radicals, for example the Na or Ca salt lignin sulfonic acid, dodecyl sulfuric acid ester or a fatty alcohol sulfate mixture made from natural fatty acids. This subheading also includes the salts of sulfuric acid esters and sulphonic acids from fatty alcohol-ethylene oxide adducts. The sulfonated benzimidazole derivatives preferably contain 2-sulfonic acid groups and a fatty acid residue with 8-22 carbon atoms. Examples of alkylarylsulfonates are the sodium, calcium or triethanolamine salts of dodecylbenzenesulfonic acid, dibutylnaphthalenesulfonic acid or a naphthalenesulfonic acid / formaldehyde condensation product. Corresponding phosphates such as, for example, also come Salts of the phosphoric acid ester of a p-nonylphenol (4-14) ethylene oxide adduct or phospholipids in question.

0049Suitable nonionic surfactants are primarily polyglycol ether derivatives of aliphatic or cycloaliphatic alcohols, saturated or unsaturated fatty acids and alkylphenols, which can contain 3 to 10 glycol ether groups and 8 to 20 carbon atoms in the (aliphatic) hydrocarbon radical and 6 to 18 carbon atoms in the alkyl radical of the alkylphenols .

0050Further suitable nonionic surfactants are the water-soluble polyethylene oxide adducts containing 20 to 250 ethylene glycol ether groups and 10 to 100 propylene glycol ether groups on polypropylene glycol, ethylenediaminopolypropylene glycol and alkylpolypropylene glycol with 1 to 10 carbon atoms in the alkyl chain. The compounds mentioned usually contain 1 to 5 ethylene glycol units per propylene glycol unit.

0051Examples of nonionic surfactants include its nonylphenol polyethoxyethanols, castor oil polyglycol ether , polypropylene-polyethylene oxide adducts , tributylphenoxypolyethoxyethanol, polyethylene glycol and octylphenoxypolyethoxyethanol .

0052Fatty acid esters of polyoxyethylene sorbitan such as polyoxyethylene sorbitan trioleate are also suitable.

0053The cationic surfactants are all quaternary ammonium salts which contain at least one alkyl radical having 8 to 22 carbon atoms as N substituents and have lower, optionally halogenated alkyl, benzyl or lower hydroxyalkyl radicals as further substituents. The salts are preferably in the form of halides, methyl sulfates or ethyl sulfates, for example the stearyltrimethylammonium chloride or the benzyldi (2-chloroethyl) ethylammonium bromide.

0054Adhesives are, in particular, those auxiliaries which bring about the cohesion of the carrier material, the auxiliaries and the active ingredients, such as gum arabic or carboxymethyl cellulose, when granulating.

0055The surfactants commonly used in formulation technology are described in the following publications:<ul id="ul0018" list-style="none"><li>"1987 International Mc Cutcheon's Emulsifiers and Detergents",</li><li>Glen Rock, NJ, USA.</li><li>Dr. Helmut Stache "Tensid Paperback"</li><li>Carl Hanser Verlag, Munich / Vienna 1981.</li></ul>

0056The preparations generally contain 0.1 to 95%, in particular 0.1 to 80%, active ingredient of the formula 1 1 to 99.9% of a solid or liquid additive and 0 to 25%, in particular 0.1 to 25% of one Surfactants.

0057In particular, preferred formulations are composed as follows: (% - = weight percent)<ul id="ul0019" list-style="none"><li>Emulsifiable concentrates:<img file="EP0337943A2_D0010.tif" /></li><li>Dusts:<img file="EP0337943A2_D0011.tif" /></li><li>Suspension concentrates:<img file="EP0337943A2_D0012.tif" /></li><li>Wettable powders:<img file="EP0337943A2_D0013.tif" /></li><li>Granules:<img file="EP0337943A2_D0014.tif" /></li><li>Scatter granules:<img file="EP0337943A2_D0015.tif" /></li></ul>

0058While concentrated agents are preferred as a commodity, the end user generally uses diluted agents. The use forms can be diluted down to 0.001% of active ingredient. The application rates are usually 0.005 to 5 kg AS / ha.

0059The agents can also contain other additives such as stabilizers, defoamers, viscosity regulators; Contain binders, adhesives and fertilizers or other active ingredients to achieve special effects.

Manufacturing examples

0060The - uncorrected - melting points in the following production examples are given in ° C.

H. 1. Compounds of formula 1

H. 1.1. N- (4-methyl-6-trifluoromethyl-pyrimidin-2-yl) -N- (2-trifluoromethyl-phenyl) urea

00613.6 g (0.026 mol) are added to a solution of 6.4 g (0.02 mol) of N- (4-methyl-6-trifluoromethyl-pyrimidin-2-yl) -2-trifluoromethylaniline in 100 ml of ethyl acetate at 3 ° C. Chlorosulfonyl isocyanate. After stirring for 2 hours at 3 ° C, 100 ml of ethyl acetate and 50 ml of ice water are added. The water phase is separated off, the organic phase is washed with brine, dried with sodium sulfate and evaporated on a rotary evaporator. The remaining crystals are triturated with hexane, filtered off and dried in vacuo at 40 ° C.

00626.1 g (83.8%) of the title compound of the formula are isolated<chemistry id="chem0010" num="0010"><img file="EP0337943A2_D0016.tif" /></chemistry>as crystals of mp 150-153 ° C (Verb. No. 1.020).

H. 1.2. N- (2,5-dichlorophenyl) -N- (4,6-dimethylpyrimidin-2-yl) urea

00634.0 g (0.012 mol) of N-chlorocarbonyl-N- (4,6-dimethylpyrimidin-2-yl) -2,5-dichloroaniline are dissolved in 50 ml of chloroform. To do this, an excess of ammonia gas is introduced. After the exothermic reaction has subsided, the reaction mixture is washed twice with water, dried with magnesium sulfate and evaporated.

0064After recrystallization from ethanol, 2.4 g (64.9%) of the title compound of the formula are obtained<chemistry id="chem0011" num="0011"><img file="EP0337943A2_D0017.tif" /></chemistry>as crystals of mp. 153 ° C (dec.) (Verb. No. 1.050).

0065The compounds of Table 1 are obtainable analogously to Preparation Examples H.1:<tables id="tabl0001" num="0001"><img file="EP0337943A2_D0018.tif" /></tables><tables id="tabl0002" num="0002"><img file="EP0337943A2_D0019.tif" /></tables><tables id="tabl0003" num="0003"><img file="EP0337943A2_D0020.tif" /></tables><tables id="tabl0004" num="0004"><img file="EP0337943A2_D0021.tif" /></tables><tables id="tabl0005" num="0005"><img file="EP0337943A2_D0022.tif" /></tables><tables id="tabl0006" num="0006"><img file="EP0337943A2_D0023.tif" /></tables><tables id="tabl0007" num="0007"><img file="EP0337943A2_D0024.tif" /></tables><tables id="tabl0008" num="0008"><img file="EP0337943A2_D0025.tif" /></tables><tables id="tabl0009" num="0009"><img file="EP0337943A2_D0026.tif" /></tables><tables id="tabl0010" num="0010"><img file="EP0337943A2_D0027.tif" /></tables><tables id="tabl0011" num="0011"><img file="EP0337943A2_D0028.tif" /></tables><tables id="tabl0012" num="0012"><img file="EP0337943A2_D0029.tif" /></tables><tables id="tabl0013" num="0013"><img file="EP0337943A2_D0030.tif" /></tables><tables id="tabl0014" num="0014"><img file="EP0337943A2_D0031.tif" /></tables><tables id="tabl0015" num="0015"><img file="EP0337943A2_D0032.tif" /></tables><tables id="tabl0016" num="0016"><img file="EP0337943A2_D0033.tif" /></tables>

H. 2. Compounds of Formula 11

H. 2.1. N- (4-methyl-6-trifluoromethyl-pyrimidin-2-yl) -2-trifluoromethylaniline

0066A suspension of 24 g (0.1 mol) of 2-trifluoromethylphenylguanidinium hydrochloride in 80 ml of tetrahydrofuran is added to a solution of 12 g (0.1 mol) of potassium tert-butoxide in 100 ml of tetrahydrofuran. After the exothermic reaction has subsided, 15.4 g (0.1 mol) of a, a, a-trifluoroacetylacetone in 20 ml of tetrahydrofuran are added. The reaction mixture is stirred at 60 ° C. for 2 hours, then evaporated on a rotary evaporator. The residue is chromatographed on silica gel with a mixture of ethyl acetate and hexane (ratio 1: 2). 18.7 g (58.2% of theory) of the title compound of the formula are obtained<chemistry id="chem0012" num="0012"><img file="EP0337943A2_D0034.tif" /></chemistry>as crystals of mp. 65-66 ° C (Verb. No. 2.020).

0067The compounds of Table II are obtainable analogously to Example H 2:<tables id="tabl0017" num="0017"><img file="EP0337943A2_D0035.tif" /></tables><tables id="tabl0018" num="0018"><img file="EP0337943A2_D0036.tif" /></tables><tables id="tabl0019" num="0019"><img file="EP0337943A2_D0037.tif" /></tables><tables id="tabl0020" num="0020"><img file="EP0337943A2_D0038.tif" /></tables><tables id="tabl0021" num="0021"><img file="EP0337943A2_D0039.tif" /></tables><tables id="tabl0022" num="0022"><img file="EP0337943A2_D0040.tif" /></tables><tables id="tabl0023" num="0023"><img file="EP0337943A2_D0041.tif" /></tables><tables id="tabl0024" num="0024"><img file="EP0337943A2_D0042.tif" /></tables><tables id="tabl0025" num="0025"><img file="EP0337943A2_D0043.tif" /></tables><tables id="tabl0026" num="0026"><img file="EP0337943A2_D0044.tif" /></tables><tables id="tabl0027" num="0027"><img file="EP0337943A2_D0045.tif" /></tables><tables id="tabl0028" num="0028"><img file="EP0337943A2_D0046.tif" /></tables><tables id="tabl0029" num="0029"><img file="EP0337943A2_D0047.tif" /></tables><tables id="tabl0030" num="0030"><img file="EP0337943A2_D0048.tif" /></tables><tables id="tabl0031" num="0031"><img file="EP0337943A2_D0049.tif" /></tables><tables id="tabl0032" num="0032"><img file="EP0337943A2_D0050.tif" /></tables>

H. 3. Compounds of Formula 111

H. 3.1. N-chlorocarbonyl-N- (4,6-dimethyl-pyrimidin-2-yl) -2,5-dichloroaniline

00685.0 g (0.018 mol) of N- (4,6-dimethyl-pyrimidin-2-yl) -2,5-dichloroaniline are dissolved in 100 ml of toluene and heated to reflux. Then a gentle stream of phosgene is introduced for 4 hours. The excess phosgene is blown out with nitrogen, the toluene solution is washed cold with water, dried with magnesium sulfate and then evaporated. 5.8 g (95.1^O/ o) the title compound of the formula<chemistry id="chem0013" num="0013"><img file="EP0337943A2_D0051.tif" /></chemistry>as crystals of mp 121-123 ° C.

Biological examples

Example B1: Pre-emergent herbicide activity

0069Immediately after sowing the test plants in seed trays, the earth's surface is treated in the greenhouse with an aqueous spray mixture corresponding to an application rate of 4 kg of active substance / hectare. The seed pans are kept in the greenhouse at 22-25 ° C and 50-70% relative humidity. After 3 weeks, the herbicidal activity is assessed using a nine-stage (1 = complete damage, 9 = no effect) rating scheme in comparison in an untreated control group.

0070Ratings of 1 to 4 (especially 1 to 3) indicate good to very good herbicidal activity. Rating grades from 6 to 9 (especially from 7 to 9) indicate a good tolerance (especially in crops).

0071In this experiment, the compounds of Table 1 show a strong herbicidal activity.

0072In this test, the following compounds of the formula I, among others, show good to very good herbicidal activity against Setaria italica and Stellaria media: Verb. 1.009, 1.016, 1.020, 1.021, 1.023, 1.032, t.037, 1.038, 1.042, 1.050, 1.052, 1.055, 1.056, 1.064, 1.065, 1.096, 1.109, 1.113, 1.132, 1.141, 1.144, 1.170, 1.219, 1.221, 1,258, 1,271, 1,332, 1,346, 1,380, 1,392, 1,459, 1,501, 1,505, 1,527, 1,528, 1,540, 1,543, 1,553, 1,638, 1,691, 1,703 and 1,712.

Example B2: Pre-emergence selective herbicidal activity

0073Immediately after sowing the seeds in flower pots with a diameter of 12-15 cm, the surface is treated with an aqueous spray mixture corresponding to an application rate of 1000 and 500 [g] AS / [ha]. The pots are left in the greenhouse at a temperature of 22-25 ° C and 50-70% relative humidity.

0074After 3 weeks, the herbicidal activity is assessed using a nine-stage (1 = complete damage, 9 = no effect) rating scheme in comparison in an untreated control group.

0075Ratings of 1 to 4 (especially 1 to 3) indicate good to very good herbicidal activity. Rating grades from 6 to 9 (especially from 7 to 9) indicate a good tolerance (especially in crops).

0076The results of this experiment are summarized in Table III below. T means good to very good tolerance (for the crop) and H means good to very good herbicidal activity (for the weeds).<tables id="tabl0033" num="0033"><img file="EP0337943A2_D0052.tif" /></tables>

Example B3: Herbicidal action for water rice (transplanted)

0077Water weeds are grown in plastic containers (425 cm² Surface, 5.0 1 volume) sown. In addition, rice is transplanted in the three-leaf stage (transplanted rice). After transplanting, the surface is filled with water. 3 days after sowing, the water level is raised to slightly above the earth's surface (3-5 mm). The test substance is applied 3 days after transplanting at a rate of 500 and 1000 [g / ha] by injecting an aqueous emulsion into the water (the application volume corresponds to 1400 I / ha). The planters are then placed in the greenhouse under optimal growth conditions for sowing, ie at 25 ° -30 ° C and high air humidity.

0078The tests are evaluated three weeks after application in a nine-stage rating scheme in comparison to the untreated control.

0079Ratings from 1 to 4 (especially from 1 to 3) indicate good to very good herbicidal activity. Credit scores of 6 to 9 (especially 7 to 9) indicate a good tolerance (especially for the rice).

0080In this test, the compounds 1.009, 1.096 and 1.141 show very good herbicidal activity against Echinochola crus galli, with very good tolerance from the rice at the same time. In addition, compound 1.141 shows very good herbicidal activity against monocharia.

Example B4: Growth inhibition in cereals

0081The plants (e.g. summer barley of the Iban variety) are sown in 15 cm plastic pots with sterile land and grown in the climate chamber at a daytime temperature of 10-15 ° C and a nighttime temperature of 5-10 ° C. The lighting duration is 13.5 hours per day with an intensity of approx. 25000 lux. 34 days after sowing and thinning on 4 plants / pot, the application is carried out with 0.3 to 3 kg of active ingredient / ha, usually formulated in 250% and in an aqueous spray mixture. The water application rate is approx. 500 I / ha. After application, the plants are placed in a greenhouse at a daily temperature of at least 10 ° C. The lighting duration is at least 13.5 hours / day.

0082Approx. Evaluation takes place 28 days after treatment. The amount of new growth is shown.

0083The tested compounds of the formula bring about a reduction in new growth compared to the untreated control.

Example B5: Growth inhibition in grasses with clover

0084A mixture of grasses (e.g. Poa, Festuca, Lolium, Bromus, Cynosurus) and clover (Trifolium pratense / repens) is sown in 15 cm plastic pots with sterile land and in the greenhouse at a daytime temperature of 21 ° C and a night temperature of 17⁰C attracted. The lighting duration is 13.5 hours / day with a light intensity of at least 7000 lux. After the emergence, the plants are cut back to a height of approx. 6 cm a week. Approx. 42 days after sowing and 1 day after the last cut, the application is carried out with 0.3 to 3 kg of active ingredient / ha, usually formulated in 250% and in an aqueous spray mixture. The water application rate is approx. 500 I / ha. Approx. Evaluation takes place 3 weeks after the treatment. The amount of new growth is measured here.

0085The tested compounds of formula I bring about a reduction in new growth compared to untreated controls.

Formulation examples

Example F1: Formulation examples for active compounds of the formula I (% = percent by weight)

a) Emulsion concentrates

0086<tables id="tabl0034" num="0034"><img file="EP0337943A2_D0053.tif" /></tables>

0087Emulsions of any desired concentration can be prepared from such concentrates by dilution with water.

b) solutions

0088<tables id="tabl0035" num="0035"><img file="EP0337943A2_D0054.tif" /></tables>

0089The solutions are suitable for use in the form of tiny drops.

c) granules

0090<tables id="tabl0036" num="0036"><img file="EP0337943A2_D0055.tif" /></tables>

0091An active ingredient solution is sprayed onto the carrier and the solvent is then evaporated off in vacuo.

d) dusts

0092<tables id="tabl0037" num="0037"><img file="EP0337943A2_D0056.tif" /></tables>

0093Ready-to-use dusts are obtained by intimately mixing the carrier substances with the active ingredient

e) wettable powder

0094<tables id="tabl0038" num="0038"><img file="EP0337943A2_D0057.tif" /></tables>

0095The active ingredient is mixed well with the additives and ground well in a suitable mill. Spray powder is obtained which can be diluted with water to give a suspension of any desired concentration.

f) extruder granules

0096<tables id="tabl0039" num="0039"><img file="EP0337943A2_D0058.tif" /></tables>

0097The active ingredient is mixed with the additives, ground and moistened with water. This mixture is extruded and then dried in an air stream.

g) coating granules

0098<tables id="tabl0040" num="0040"><img file="EP0337943A2_D0059.tif" /></tables>

0099The finely ground active ingredient is applied evenly in a mixer to the kaolin moistened with polyethylene glycol. In this way, dust-free coating granules are obtained.

h) suspension concentrate

0100<tables id="tabl0041" num="0041"><img file="EP0337943A2_D0060.tif" /></tables>

0101The active ingredient is intimately mixed with the additives. This gives a suspension concentrate from which suspensions of any desired concentration can be prepared by dilution with water.