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MXPA01000207A - Substituted acylamino phenyl uracils - Google Patents

Substituted acylamino phenyl uracils

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Publication number
MXPA01000207A
MXPA01000207A MXPA/A/2001/000207A MXPA01000207A MXPA01000207A MX PA01000207 A MXPA01000207 A MX PA01000207A MX PA01000207 A MXPA01000207 A MX PA01000207A MX PA01000207 A MXPA01000207 A MX PA01000207A
Authority
MX
Mexico
Prior art keywords
carbon atoms
substituted
chlorine
cyano
fluorine
Prior art date
Application number
MXPA/A/2001/000207A
Other languages
Spanish (es)
Inventor
Ingo Wetcholowsky
Roland Andree
Dieter Feucht
Rolf Pontzen
Mark Wilhelm Drewes
Original Assignee
Bayer Aktiengesellschaft
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Filing date
Publication date
Application filed by Bayer Aktiengesellschaft filed Critical Bayer Aktiengesellschaft
Publication of MXPA01000207A publication Critical patent/MXPA01000207A/en

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Abstract

The invention relates to novel substituted acylamino phenyl uracils of general formula (I) in which n, A, Ar, Q1, R1, R2, R3, R4, R5 and R6 have the meanings cited in the description. The invention also relates to a method for producing said substituted acylamino phenyl uracils and to their use as herbicides.

Description

ACILAMINOFENIL-SUBSTITUTE URECILS FIELD OF THE INVENTION The invention relates to new substituted acylaminophenyl-uracils, to processes for their preparation and to their use as herbicides.
Background of the Invention Certain substituted aryluracils are already known from the literature (of patents) (see EP-A-408382, US-A 5084084, US-A 5127935, US-A 51514755, EP-A-563384, US-A-5356863, WO-A-95/29168, WO-A-96/35679, WO-A-97/01542, WO-A-97/09319, WO -A- 98/06706). However, these compounds have not yet acquired any special significance.
DETAILED DESCRIPTION OF THE INVENTION New substituted acylaminophenyl-uracils of the general formula (I) have now been found REF .: 126188 where n means the numbers 0 or 1, A means alkanediyl (alkylene) or cycloalkanediyl substituted respectively, or - provided that when n means 1- it also means a single bond or is bridged with Ar via an alkanediyl group, Ar means aryl, arylalkyl, heterocyclyl or heterocyclylalkyl respectively substituted, where appropriate, Q means O (oxygen), S (sulfur), SO, S02, NH or N (alkyl), means hydrogen, amino or alkyl in case substituted, means carboxy, cyano, carbamoyl, thiocarbamoyl or means optionally substituted alkyl or alkoxycarbonyl, R3 signifies hydrogen, halogen or optionally substituted alkyl, R4 signifies hydrogen, cyano, carbamoyl, thiocarbamoyl or halogen, R5 signifies cyano, carbamoyl, thiocarbamoyl, halogen or means alkyl or alkoxy substituted respectively where appropriate, and R6 means hydrogen or means alkyl, alkyl alkenyl, alkoxycarbonyl, alkylsulfonyl, alkenyl, alkenylcarbonyl, alkenylsulfonyl, alkynyl, cycloalkylcarbonyl, cycloalkylsulfonyl, arylcarbonyl, arylsulfonyl, arylalkylcarbonyl, arylalkysulfonyl, heterocyclylcarbonyl or heterocyclylsulfonyl respectively substituted, if appropriate. In the definitions the hydrocarbon chains, such as alkyl or alkanediyl - even in combination with heteroatoms, as in alkoxy - are respectively straight-chain or branched chain.
Insofar as the compounds according to the invention of the general formula (I) contain asymmetrically substituted carbon atoms, the invention relates respectively to the R enantiomers and the S enantiomers, as well as to arbitrary mixtures of these enantiomers, especially the racemates Preferably, A means alkanediyl (alkylene) with 1 to 6 carbon atoms or cycloalkanediyl with 3 a 6 carbon atoms, respectively substituted by halogen or -in the case where n means 1- also means a single bond or is linked to Ar through an encapsulated ring with 1 to 3 carbon atoms, Ar preferably means aryl or arylalkyl respectively substituted, respectively with 6 or 10 carbon atoms in the aryl group and, optionally, 1 to 4 carbon atoms in the alkyl part, or means heterocyclyl or heterocyclylalkyl respectively substituted with one to five carbon atoms and at least one heteroatom (up to 4 nitrogen atoms and / or optionally 1 or 2 oxygen or sulfur atoms), optionally each respective substituent being preferably the following enumeration: nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, alkyl having 1 to 4 carbon atoms, halogenalkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, haloalkoxy with 1 to 4 carbon atoms carbon, alkylthio with 1 to 4 carbon atoms, halogenalkylthio with 1 to 4 carbon atoms, alkylsulfinyl with 1 to 4 carbon atoms, haloalkylsulfini with 1 to 4 carbon atoms, alkylsulfonyl with 1 to 4 carbon atoms, halogenoalkylsulfonyl with 1 to 4 carbon atoms, alkylamino with 1 to 4 carbon atoms, di- (alkyl with 1 to 4 carbon atoms) -amino , alkylcarbonyl with 1 to 4 carbon atoms, alkoxycarbonyl with 1 to 4 carbon atoms, alkylaminocarbonyl with 1 to 4 carbon atoms, di- (C 1 -C 4 -alkylamino) -aminocarbonyl, di- (C 1 -C 4 -alkyl) -amino-sulfonyl, Preferably, Q means 0 (oxygen), S (sulfur), SO, S02, NH or N (alkyl having 1 to 4 carbon atoms), Preferably R 1 is hydrogen, amino or alkyl having 1 to 6 carbon atoms, optionally substituted by cyano, carboxy, halogen or alkoxy with 1 to 4 atoms of carbon or by alkoxycarbonyl having 1 to 4 carbon atoms, preferably R2 means carboxy, cyano, carbamoyl, thiocarbamoyl or means alkyl or alkoxycarbonyl with 1 to 6 carbon atoms in the alkyl groups, respectively substituted, if appropriate, by cyano , by halogen or by alkoxy with 1 to 4 carbon atoms, Preferably, R3 means hydrogen, halogen or alkyl having 1 to 6 carbon atoms, optionally substituted by halogen, MRIMttattÍMi? Preferably, R 4 is hydrogen, cyano, carbamoyl, thiocarbamoyl, fluorine or chlorine. Preferably, R 5 is cyano, carbamoyl, thiocarbamoyl, halogen or means alkyl or alkoxy with 1 to 4 carbon atoms, each optionally substituted by halogen, and Preferably, R6 means hydrogen, means alkyl, alkylcarbonyl, or alkoxycarbonyl with 1 to 6 carbon atoms in the alkyl groups, each optionally substituted by cyano, by halogen, or by alkoxy with 1 to 4 carbon atoms, means alkylsulfonyl with 1 to 6 carbon atoms, optionally substituted by halogen, means alkenyl, alkenylcarbonyl, alkenylsul fonyl or alkynyl with respectively up to 6 carbon atoms, each optionally substituted by halogen, means cycloalkylcarbonyl or cycloalkylsulfonyl with respectively 3 to 6 carbon atoms carbon in the cycloalkyl groups, respectively substituted optionally halogen means arylcarbonyl, arylsulfonyl, arylalkylcarbonyl or arylalkylsulfonyl with 6 or 10 carbon atoms in the aryl groups and, optionally, 1 to 4 carbon atoms in the alkyl part, respectively substituted, if appropriate, by nitro, by cyano, by halogen, by alkyl with 1 to 4 carbon atoms, by halogenalkyl with 1 to 4 carbon atoms, by alkoxy with 1 to 4 carbon atoms, by halogenalkoxy with 1 to 4 carbon atoms, by alkylthio with 1 to 4 carbon atoms, by haloalkyl thio with 1 to 4 carbon atoms, for alkylsulfinyl with 1 to 4 carbon atoms, for halogenalkylsulfonyl with 1 to 4 carbon atoms, for alkylsulfonyl with 1 to 4 carbon atoms, for halogenalkylsulfonyl with 1 to 4 carbon atoms, for alkylcarbonyl with 1 to 4 carbon atoms, by alkoxycarbonyl with 1 to 4 carbon atoms or by di- (alkylamino with 1 to 4 carbon atoms) -sulfonyl, or means heterocyclylcarbonyl or heterocyclylsulfonyl with 1 to 5 carbon atoms and 1 to 4 atoms of nitrogen and / or 1 or 2 oxygen or sulfur atoms, respectively substituted, if appropriate, by nitro, by cyano, by halogen, by alkyl with 1 to 4 carbon atoms, by halogenalkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, for halogenalkoxy with 1 to 4 carbon atoms, for alkylthio with 1 to 4 carbon atoms, for halogenalkylthio with 1 to 4 carbon atoms, for alkylsulfinyl with 1 to 4 carbon atoms, for haloalkyl ulfinyl with 1 to 4 carbon atoms, for alkylsulfonyl with 1 to 4 carbon atoms, for halogenalkylsul fonyl with 1 to 4 carbon atoms, for alkylcarbonyl with 1 to 4 carbon atoms, for alkoxycarbonyl with 1 to 4 carbon atoms or by di- (C1-C4-alkylamino) -sulfonyl, more preferably, methylene, ethane-1,1-diyl (ethylidene), ethane-1,2-diyl (dimethylene), propane- 1, 1-diyl (propylidene), propane-1,2-diyl or propane-1,3-diyl (trimethylene), cyclopropane-1,1-diyl, cyclopropane-1,2-diyl, cyclobutane-1, 1-diyl, cyclopentane-1,1-diyl or cyclohexane-1,1-diyl respectively substituted, where appropriate, by fluorine and / or chlorine, or means - in the case where n means 1 - also a single bond, or is linked to Ar through a 1,2-ethanediyl group (dimethylene), more preferably, means phenyl, naphthyl, benzyl, 1-phenylethyl, 2-phenyl-ethyl, 1-phenyl. -propyl, 2-f-enyl-propyl or 3-f-enyl-propyl respectively substituted, or means heterocyclyl or heterocyclylalkyl, respectively substituted, if appropriate, from the series consisting of oxiranyl, oxiranylmethyl, oxetanyl, oxetanylmethyl, furyl, furylmethyl, tetrahydrofuranyl, tetrahydrofurylmethyl, thienyl, thienylmethyl, tetrahydrothienyl, tetrahydrothienylmethyl, benzofuryl, benzofurylmethyl, dihydrobenzofuryl, dihydrobenzyl furylmethyl, benzothienyl, benzothienylmethyl, pyrrolyl, pyrrolylmethyl, pyrazolyl, pyrazolylmethyl, pyranyl, piranilmetilo, benzopyranyl, benzopiranilmetilo, dihydrobenzopyranyl, dihidrobenzopiranilmetilo, tetrahydrobenzo pyranyl, tetrahidrobenzopiranilmetilo, pyridinyl, pyridinylmethyl, pyrimidinyl, pyrimidinylmethyl, being able to take the possible substituents, respective, preferably as follows enumeration: nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, difluoromethylthio, trifluoromethylthio, methylsulphinyl, n- or i-propylsulfinyl, trifluoromethyl-sulphonyl, methylsulfonyl, ethylsulphonyl, n- or i-propylsulfonyl, trifluoromethyl sulphonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t- butylamino, dimethylamino, , J = '- - - - ----- ^ - «i *» > * ^ ----- > --- ^ - ~ - ~ _. "- JM ^ J ^^ e3, diethylamino, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i- propylaminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl, dimethylaminosul fonyl, diethylaminosul fonyl, more preferably, Q means 0 (oxygen), S (sulfur), SO, S02, NH or N (methyl), particularly preferably, R 1 is hydrogen, amino or methyl or ethyl substituted, where appropriate, by cyano, fluorine, chlorine, methoxy or ethoxy, particularly preferably R 2 is carboxy, cyano, carbamoyl or thiocarbamoyl or is methyl; ethyl, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl substituted, where appropriate, by cyano, fluorine, chlorine, methoxy or ethoxy, particularly preferably - ~ "« a - »- ^ - - - - -a lte ~ jtefalM - *** ^ -. ~~~ i *, ^ --_ -» ^ - ^^ - ^ _ R3 means hydrogen , fluorine, chlorine, bromine or methyl, ethyl, n- or i-propyl substituted respectively by fluorine or chlorine, particularly preferably R 4 is hydrogen, fluorine or chlorine, R 5 is preferably cyano, Carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or means methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy substituted respectively by fluorine or chlorine, particularly preferably R6 means hydrogen, means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, acetyl, propionyl, n- or i-butyroyl, n-, i-, or sec. -valeroyl , pivaloyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl respectively substituted, where appropriate, by cyano, by fluorine, by chlorine, by methoxy or by ethoxy, means methanesulfonyl, ethylsulphonyl, non-propylsulphonyl, n-, i-, s - or t-butylsulfonyl sub settled respectively If appropriate, by fluorine and / or chlorine, it means ethenyl, propenyl, butenyl, ethenylcarbonyl, propanylcarbonyl, butenylcarbonyl, ethynyl, propynyl, or butynyl substituted, where appropriate, by fluorine, chlorine and / or chlorine. bromine, means cyclopropylcarbonyl, ciclopropi lmeti Icarboni it, cyclobutyl-carbonyl, ciclobutilmetilcarbonilo, cyclopentylcarbonyl, cyclopent ylmethyl-carbonyl, cyclohexylcarbonyl, lmetil cyclohexy carbonyl, cyclopropyl-sulfonyl, ciclopropilmeti fonilo lsul, ciclobutilmetilsulfonilo, cyclopentyl-sulfonyl, ciclopentilmetilsulfonilo, cyclohexylsulfonyl and cyclo- hexylmethylsulfonyl substituted, where appropriate, by fluorine, chlorine and / or bromine, means benzoyl, phenylsulfonyl, phenylacetyl, phenylpropionyl, benzylsulphonyl or phenylethylsulfonyl, respectively substituted by nitro, by cyano, by fluorine, by chlorine, by bromine, by methyl, by ethyl, by n- or i-propyl, n-, i-, s- or t-butyl, by triflu ormethyl, by methoxy, by ethoxy, by n- or i-propoxy, by n-, i-, s- or t-butoxy, by difluoromethoxy, by trifluoromethoxy, by methylthio, by ethylthio, by n- or i-propylthio, by n-, i-, s- or t-butylthio, by difluoromethylthio, by trifluoromethylthio, by methylsulfinyl, by ethylsulfinyl, by n- or i-propylsulfinyl, by trifluoromethyl-sulphonyl, by methylsulfonyl, by ethyl sulphonyl, by n- or i-propylsulfonyl, by tri-fluoromethylsulfonyl, by acetyl, by propionyl, by n- or i-butyroyl, by methoxycarbonyl, by ethoxycarbonyl, by n - or i-propoxycarbonyl, by dimethylaminosul fonyl or by dialkylsulphonyl, or means heterocyclylcarbonyl or heterocyclylsulfonyl of the series consisting of furylcarbonyl, furylsulfonyl, thienylcarbonyl, thienylsul fonyl, pyrazolylcarbonyl, pyrazolysulfonyl, pyridinylcarbonyl, pyridinyl sulphonyl, quinolinylcarbonyl, quinolinyl sulfonyl, pyrimidiylcarbonyl , pyrimidinylsulfonyl, each optionally substituted by nitro, by cyano, by fluorine, by chlorine, by bromine, by methyl, by ethyl, by n- or i-propyl, by n-, i-, s- or t-butyl, by trifluoromethyl, by methoxy, by ethoxy, by n- or i-propoxy, by n-, i-, s- or t-butoxy, by di-fluoromethoxy, by trifluoromethoxy, by methylthio, by ethylthio, by n- or i-propylthio, by n-, s- or t-butylthio, by difluoromethylthio, by trifluoromethylthio, by methylsulfinyl, by ethylsulfinyl, by n- or i-propylsulfinyl, by trifluoromethylsulphinyl , by methylsulfonyl, by ethyl sulphonyl, by n- or i-propylsulfonyl, by trifluoromethylsulfonyl, by acetyl, by propionyl, by n- or i-butyroyl, by methoxycarbonyl, by ethoxycarbonyl, by n- or i-propoxycarbonyl, by dimethylaminosul fonyl or by diethyl aminosulfon, very particularly preferably, methylene, ethane-1, 1-diyl (ethylidene) or ethane-1,2-diyl (dimethylene) is very preferably used, . ^ - ^ ?? USSt ^^^ .. > .
Ar means phenyl, naphthyl or benzyl substituted respectively where appropriate, it being possible to take the respective substituents, especially from the following enumeration: nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n- , i-, s- or t-butyl, trifluoromethyl, methoxy, "ethoxy, n- or i- propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulphinyl, n- or i-propylsulfinyl, trifluoromethyl-sulphonyl, methylsulfonyl, ethylsulphonyl, n- or i-propylsulphonyl, trifluoromethyl-sulphonyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, very preferably, Q means O (oxygen), very especially Preferred R 1 is hydrogen, amino or methyl, very preferably R 2 is trifluoromethyl, very particularly preferably "" '"• * - * -?' Ii»? Ii miliar - - ^ mi Sii-i ß táiiiátltí R3 means hydrogen, chlorine or methyl, very particularly preferably, R4 means hydrogen, fluorine or chlorine, in a very particularly preferably, R 5 is cyano, carbamoyl, thiocarbamoyl, chloro or bromo, most preferably R 6 is hydrogen, means methanesulfonyl, ethylsulphonyl, n- or i-propylsulfonyl, n-, i-, s- or t-butylsulfonyl , where appropriate substituted by fluorine and / or chlorine, or means cyclopropyl sulphon substituted respectively by fluorine and / or by chlorine, most preferably Ar means phenyl or naphthyl, respectively, optionally substituted; possible substituents, respective, especially from the following enumeration: nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy , n- or i- propoxy, difluoromethoxy, tr iflúormetoxi, iniiHÉlntir'Hi'ii-mtiiiiiifi i * - "• ** - * - - * - - • ^ - ~ -. -. -?. .. methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulphinyl, ethylsulphinyl, n- or i-propyl-sulfinyl, trifluoromethyl-sulphonyl, methylsulfonyl, ethyl sulphonyl, n- or i-propylsulfonyl, trifluoromethyl-sulphonyl, methoxycarbonyl, ethoxycarbonyl , n- or i- propoxycarbonyl.
The definitions of the residues given above in a general manner or indicated in the preferred ranges, are valid both for the final products of the formula (I) and also, correspondingly, for the starting products or for the necessary intermediate products respectively for obtaining. These definitions of the remains can be combined arbitrarily with each other, ie even between the preferred ranges indicated. Preferred according to the invention are the compounds of the formula (I), in which a combination of the meanings indicated above is preferentially presented.
It is particularly preferable according to the invention to the compounds of the formula (I), in which a combination of the abovementioned meanings is particularly preferably present. According to the invention, the compounds of the formula (I) are very particularly preferred, in which a combination of the meanings indicated above is very particularly preferably present. More preferred according to the invention are the compounds of the formula (I), in which a combination of the meanings indicated above is presented in the most preferred manner. Examples of compounds according to the invention of the general formula (I) have been indicated in the following groups. Group 1.
In this case, Ar has the meanings indicated in the following enumeration: 2-cyano-phenyl, 3-cyano-2-cyano-phenyl, 3-cyano -phenyl, 4-cyano-phenyl, 2-fluoro-phenyl, 3-fluoro-phenyl, 4-fluoro-phenyl, 2,3-difluoro-phenyl, 2,4-difluoro-phenyl, 2,5-difluoro-phenyl , 2,6-difluoro-phenyl, 3,4-difluoro-phenyl, 3-5-difluoro-phenyl, 2-chloro-phenyl, 3-chloro-phenyl, 4-chloro-phenyl, 2,3-dichloro-phenyl, 2,4-dichloro-phenyl, 2,5-dichloro-phenyl , 2,6-dichloro-phenyl, 3,4-dichloro-phenyl, 3,5-dichloro-phenyl, 2-bromo-phenyl, 3-bromo-phenyl, 4-bromo-phenyl, 2-methyl-phenyl, -methyl-phenyl, 4-methyl-phenyl, 2,3-dimethyl-phenyl, 2,4-dimethyl-phenyl, 2,5-dimethyl-phenyl, 2,6-dimethyl-phenyl, 3,4-dimethyl-phenyl , 3, 5-dimethyl-phenyl, 2-trifluoromethyl-phenyl, 3-trifluoromethyl-phenyl, 4-trifluoromethyl-phenyl, 2-methoxy-phenyl, 3-methoxy-phenyl, 4-methoxy-phenyl, 2,4-dimethoxy -phenyl, 2,5-di-methoxy-phenyl, 2,6-dimethoxy-phenyl, 3,4-dimethoxy-phenyl, 2-difluoromethoxy-phenyl, 4-difluoromethoxy-phenyl, 2-trifluoromethoxy-phenyl, 4-trifluoromethoxy -phenyl, 2-chloro-4-methyl-phenyl, 4-chloro-2-methyl-phenyl, 2-fluoro-4-chloro-phenyl, 2-chloro-4-fluoro-phenyl, 2-chloro-4-bromo- phenyl, 2-bromo-4-chloro-phenyl, 2-fluoro-4-bromo-phenyl, 2-bromo-4-fluorophenyl, 4-fluoro-2-methyl-phenyl, 4-bromo-2-methyl-phenyl. Group 2.
In this case Ar has the meaning indicated above in group 1. Group 3. "-» ---- »" * - - ^ árá¡¡ it? Iá¡ a¿i? ? íi.
In this case Ar has the meaning indicated above in group 1. Group.
In this case Ar has the meaning indicated above in group 1. Group 5. i i I II i i n i mil f 11 i i In this case Ar has the meaning indicated above in group 1 Group 6.
In this case Ar has the meaning indicated above in group 1. Group 7.
• Ma ^ dhl ^ kÉriÉfek In this case Ar has the meaning indicated above in group 1. Group 8 In this case Ar has the meaning indicated above in group 1. Group 9. alUtriüMt In this case Ar has the meaning indicated above in group 1. Group 10.
In this case Ar has the meaning indicated above in group 1. Group 11.
^^^^ ¡¡^^^ ¿^^^ Q ^^^^^ r ^ In this case Ar has the meaning indicated above in group 1. Group 12.
In this case Ar has the meaning indicated above in group 1. Group 13. iJ? bh-é - ^? UiM? tti In this case Ar has the meaning indicated above in group 1. Group 1.
In this case Ar has the meaning indicated above in group 1. Group 15.
In this case Ar has the meaning indicated above - in group 1 Group 16.
In this case Ar has the meaning indicated above in group 1. The novel substituted acylaminophenyl-uracils of the general formula (I) have interesting biological properties. These are characterized especially by a powerful herbicidal activity. The new substituted acylaminophenyl-uracils of the general formula (I) are obtained if aminophenyl-uracils of the general formula (II) are reacted wherein R1, R1 R3, R R 'R6 have the meaning indicated above, with acylating agents of the general formula (III) wherein n, A, Ar and Q have the meaning indicated above, and X means halogen, if appropriate in the presence of an auxiliary agent of the reaction and, if appropriate, in the presence of a diluent, and if necessary subsequently carried out within the scope of the definition of the substituents, in a manner usual, electrophilic or nucleophilic reactions or oxidation or reduction. The compounds of the general formula (I) can be converted, according to customary methods, into other compounds of the general formula (I) according to the above definition, for example by means of amination or alkylation, for example R 1: H - »NH 2, CH 3, reaction with dicyan or with hydrogensulfite (for example Br? CN, CN -> CSNH2, see the preparation examples).
If, for example, l- (2,4-dichloro-5-methylsulfonylamino-phenyl) -4-difluoronti 1-3,6-dihydro-2,6-dioxo-l (2H) pyrimidine and the chloride of ( -chloro-2-methyl-phenoxy) acetyl as starting materials, the development of the reaction in the case of the process according to the invention can be schematized by means of the following formula scheme: á ± fi? = itfe.
The aminophenyluracils, to be used as starting materials in the process according to the invention for the preparation of the compounds of the formula (I) are generally defined by the formula (II). In the formula (II), R1, R2, R3, R4, R5 and R6 preferably have those meanings which have already been mentioned above, preferably, very preferably or very particularly preferably for R1, R2, R3, R4 , R5 and R6 in relation to the description of the compounds of the formula (I) according to the invention.
The starting materials of the general formula (II) = are known and / or can be prepared according to processes known per se (cf. EP-A-408382, EP-A-648749, WO-A-97/01542). The acylating agents to be further used as starting materials in the process according to the invention are generally defined by the formula (III). In the formula (III), n, A, Ar and Q preferably have those meanings that have already been mentioned above, preferably, very preferably, very particularly preferably and most preferably for n, A, Ar and Q in relation to the description of the compounds of the formula (I) according to the invention; preferably X means fluorine, chlorine or bromine, especially chlorine. The starting materials of the general formula (III) are chemical products for known syntheses. The process according to the invention for the preparation of the compounds of the general formula (I) is preferably carried out using a reaction auxiliary agent. As auxiliary agents of the reaction, they come into consideration in * I * ?? ~ * ¡? ~ - *. this case, in general, the bases or acceptors of usual inorganic or organic acids. These preferably include acetates, amides, carbonates, bicarbonates, hydrides, hydroxides or alkanolates of alkali metals or alkaline earth metals, such as, for ele, sodium, potassium or calcium acetate, lithium amide, sodium acetate, potassium or calcium, sodium, potassium or calcium carbonate, sodium, potassium or calcium bicarbonate, lithium, sodium, potassium or calcium hydride, lithium, sodium, potassium hydroxide or calcium, methanolate, ethanolate, n- or i-propanolate, n-, i-, s- or sodium or potassium t-butanolate; also basic organic nitrogenous compounds, such as, for ele, trimethylamine, triethylamine, tripropylamine, tributylamine, ethyldiisopropylamine, N, N-dimethyl-1-cyclohexylamine, dicyclohexylamine, ethyldicyclohexylamine, N, N-dimethyl-aniline, N, N-dimethyl. -benzylamine, pyridine, 2-methyl-, 3-methyl-, 4-methyl-, 2, 4-dimethyl-, 2,6-dimethyl-, 3,4-dimethyl- and 3,5-dimethyl-pyridine, -ethyl-2-methyl-pyridine, 2-dimethylamino-pyridine, N-methyl-piperidine, 1, -diazabicyclo [2, 2, 2] -octane (DABCO), 1.5- - • ^^ Mat * a ^ - diazabicyclo [, 3, 0] -non-5-ene (DBN), or 1,8-diazabicyclo [5, 4, 0] -undec-7-ene (DBU) . The process according to the invention for the preparation of the compounds of the general formula (I) is preferably carried out using a diluent. Suitable diluents for carrying out the process according to the invention are all inert organic solvents. These include, in particular, aliphatic, alicyclic or aromatic halogenated hydrocarbons, such as, for ele, benzine, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; ethers, such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; ketones, such as acetone, butanone, or methyl isobutyl ketone; nitriles, such as acetonitrile, propionitrile or butyronitrile; amides, such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-formanilide, N-methyl-pyrrolidone or hethylphosphorotriamide; esters such as methyl acetate or ethyl acetate, sulfoxides, such as dimethylsulfoxide, alcohols, such as methanol, n- or i-propanol ethanol, ethylene glycol onomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, their mixtures with water or pure water. The reaction temperatures in carrying out the process according to the invention can vary within wide limits. In general, work is carried out at temperatures between 0 ° C and 150 ° C, preferably between 10 ° C and 120 ° C. The process according to the invention is generally carried out under normal pressure. However, it is also possible to carry out the process according to the invention under higher pressure or at a lower pressure, generally between 0.1 bar and 10 bar. For carrying out the process according to the invention, the starting materials are generally used in approximately equimolar amounts. However, it is also possible to use one of the components in a larger excess. The reaction is carried out, in general, in a suitable diluent in the presence of an auxiliary agent of the reaction and the reaction mixture is stirred, in general, during several hours at the necessary temperature. The preparation is carried out according to usual methods (see the preparation eles). The active compounds according to the invention can be used as defoliants, desiccants, agents for removing harmful plants, especially for destroying weeds. By weeds, in the broadest sense, we must understand the plants that grow in places where they are unwanted. The fact that the substances according to the invention act as total or selective herbicides depends essentially on the amount used. The active products, according to the invention can be used, for example, in the following plants: Dicotyledonous bad herbs of the kinds: Sinapis Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum.
Dicotyledonous crops of the classes: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cucurbita. Bad monocotyledonous herbs of the following kinds: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Oats, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum , Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera. Cultures of monocotyledonous classes: Oryza, Zea, Triticum, Hordeum, Avena, Sécale, Sorghum, Panicum, Saccharum, Ananas, Asparagus, Allium. The use of the active compounds according to the invention is, however, not limited in any way to these classes, but they also extend to other plants in the same way. The compounds are suitable, depending on the concentration, to completely combat the weeds, for example, in industrial and road installations and in roads and squares, with and without tree growth. In the same way, compounds can be used to control weeds in permanent crops, for example, in forest facilities, ornamental trees, fruit trees, vineyards, citrus trees, walnut trees, bananas, coffee, tea, rubber oil palm, cocoa, fruit-tea-berries and ornamental plants, ornamental and sporting plants and on surfaces - of meadows and to selectively control weeds in crops mono-annual. The compounds of the formula (I) according to the invention are suitable for the control of monocotyledonous and dicotyledonous weeds both in the pre-emergence procedure and in the post-emergence process. They show a high herbicidal activity and a broad spectrum of activity when they are used on the soil and on the aerial parts of the plants. The active ingredients can be converted into the customary formulations, such as solutions, emulsions, sprayable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension-emulsion concentrates, natural and synthetic materials impregnated with the active compound , as well as micro-encapsulations in polymer materials. These formulations are prepared in known manner, for example, by mixing the active ingredients with extender materials, that is, with liquid solvents and / or solid diluents, if appropriate, using surfactants, that is, emulsifiers and / or dispersants and / o foam generating means. When using water as a filler, it is also possible, for example, to use organic solvents as auxiliary solvents. The following are particularly suitable liquid solvents: aromatic hydrocarbons, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic hydrocarbons and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane, or paraffins, for example, fractions of crude oil, alcohols such as butanol, or glycol, as well as their esters and ethers, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone, or cyclohexanone, strongly polar solvents A'- ~ - ^ - such as dimethylformamide and dimethylsulfoxide, as well as water. Suitable solid excipients are: for example, ammonium salts and natural mineral flours, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earths and molten synthetic minerals, such as silicic acid, highly dispersed, aluminum oxide and silicates, as solid excipients for granulates broken and fractionated natural minerals such as calcite, marble, pumice, sepiolite, dolomite, as well as synthetic granules of inorganic and organic flours, as well as granulates of organic materials such as sawdust can be used , husks of coconut, corn ears and tobacco stems; as emulsifiers and / or foam generators, nonionic and anionic emulsifiers, such as polyoxyethylenated fatty acid esters, polyoxyethylenated fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulfates, arylsulphonates, as well as the hydrolysis products of albumin; as dispersants they enter -au llfal Ét ^ iiudi. lWllli 11 il 'liíílílttllí.ll lll lj Li Li et I 11 (111: for example, lignin-sulphite waste liquors and methylcellulose. In the formulations Tackifiers such as carboxymethylcellulose and natural and synthetic polymers in powder, granules or of latex, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, as well as natural phospholipids, such as cephalin and lecithin, and synthetic phospholipids.Other additives can be mineral and vegetable oils.Dyes, such as inorganic pigments, can be used, example, iron oxide, titanium oxide, Prussian blue and organic dyes, such as alizarin dyes, azo dyes and metal phthalocyanine dyes and trace nutrients, such as iron, manganese, boron, copper, cobalt, molybdenum salts and zinc The formulations generally contain between 0.1 to 95% by weight of active compound, preferably between 0.5 and 90% by weight. The active compounds according to the invention can find application as such or in their formulations also in mixture with herbicides known for the fight against weeds being possible finished formulations or tank mixes. For the mixtures are known herbicides, for example acetochlor, acifluorfen (-sodium), aclonifen, alachlor, alloxydim (-sodium), Ametryne, Amidochlor, amidosulfuron, anilofos, Asulam, Atrazine, Azafenidin, Azimsulfuron, benazolin (-ethyl ), Benfuresate, Bensulfuron (-methyl), Bentazon, Benzofenap, Benzoylprop- (ethyl), Bialaphos, Bifenox, Bispyribac (-sodium), Bromobutide, Bromophenoxy, Bromoxynil, Butachlor, Butroxydim, Butylate, Cafenstrole, Caloxydim, Carbetamide, Carfentrazone (-ethyl), Chlomethoxyfen, Chloramben, Chloridazon, Chlorimuron (-ethyl), Chlornitrofen, Chlorsulfuron, Chlortoluron, Cinidon (-ethyl), Cinmethylin, Cinosul furon , clethodim, clodinafop (-propargilo), clomazone, clomeprop, clopyralid, Clopyrasulfuron (-methyl), cloransulam (-methyl), cumyluron, Cyanazine, Cybutryne, cycloate, cyclosulfamuron, cycloxydim, Cyhalofop (-butyl), 2,4-D , 2,4-DB, 2,4-DP, Desmedipham, Diallate, Dicamba, Diclofop (-methyl.), Diclosulam, Diethatyl (ethyl), Difenzoquat, Diflufenican, Diflufenzopyr, Dimefuron, Dimepiperate, Dimethachlor, Dimethametryn, Dimethenamid, Dimexyflam, Dinitramine, Diphena id, Diquat, Dithiopyr, Diuron, Dy rum, Epoprodan, EPTC, Esprocarb, Ethalfluralin, Ethametsulfuron (-methyl), Ethofumesate, Ethoxyfen, Ethoxysulfuron, Etobenzanid, fenoxaprop (-P-ethyl), Flamprop (-isopropyl), Flamprop (-isopropyl-L), Flamprop (-methyl), flazasulfuron, fluazifop (-P-butyl), Fluazolate, Flucarbazone, Flufenacet, Flumetsulam, flumiclorac ( -pentyl), flumioxazin, flumipropyn, Flumetsulam, fluometuron, fluorochloridone, fluoroglycofen (-ethyl), flupoxam, flupropacil, Flurpyrsulfuron (-methyl, -sodium), Flurenol (-butyl), Fluridone, Fluroxypyr (-methyl), Flurprimidol, Flurtamone, Fluthiacet (-methyl), Fluthiamide, Fomesafen, Glufosinate (-ammonium), Glyphosate (-isopropylammonium), Halosafen, Haloxyfop (-ethoxyethyl), Haloxyfop (-P-methyl), Hexazinone, Imazamethabenz (-methyl), Imazamethapyr, Imazamox, Imazapic, Imazapyr, Imazaquin, Imazethapyr, Imazosulfuron, Iodosulfuron, Ioxynil, Isopropalin, Isoproturon, Isouron, Isoxaben, Isoxachlortole, Isoxaflutole, Isoxapyrifop, Lactofen, Lenacil, Linuron, MCPA, MCPP, Mefenacet, Mesotrione, Metamitron, Metazachlor, Methabenzthiazuron, Metobenzuron, Metobromuron, (alpha-) Metolachlor, Metosulam, Metoxuron, Metribuzin, Metsulfuron ( -methyl), Molinate, Monolinuron, Naproanilide, Napropamide, Neburon, Nicosulfuron, Norflurazon, Orbencarb, Oryzalin, Oxadiargyl, Oxadiazon, Oxasulfuron, Oxaziclomefone, Oxyfluorfen, Paraquat, Pelargonic acid, Pendimethalin, Pentoxazone, Phenmedipham, Piperophos, Pretilachlor, Primisulfuron (-methyl), prometryn, propachlor, propanil, propaquizafop Propisochlor, propyzamide, prosulfocarb, prosulfuron, Pyraflufen (-ethyl), Pyrazolate, Pyrazosul furon (ethyl), pyrazoxyfen, Pyribenzoxim, pyributicarb, Pyridate, Pyriminobac (-sodium), Pyrithiobac (-sodium), Quinchlorac, Quinmerac, Quinoclamine, Quizalofop (-P-ethyl), Qui zalofop (-P-tefuryl), Rimsulfuron, Sethoxydim, Simazine, Simetryn, Sulcotrione, Sulfentrazone, Sulfometuron (-methyl), Sulfosate, Sulfosulfuron, Tebutam, Tebuthiuron, Tepraloxydim, Terbuthylazine, Terbutryn, Thenylchlor, Thiafluamide, Thiazopyr, Thidiazimin, Thifensulfuron (-met ilo), Thiobencarb, - ^ -. ^ - ^^ i Thiocarbazil, Tralkoxydim, Triallate, Triasulfuron, Tribenuron (-methyl), Triclopyr, Tridiphane, Trifluralin and Triflusulfuron. It is also possible to mix with other known active ingredients, such as fungicides, insecticides, acaricides, nematicides, products that protect against ingestion by birds, nutrient products for plants and agents that improve the structure of the soil. The active products can be used as such, in the form of their formulations or in the forms of application prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granulates. The application is carried out in a conventional manner, for example by watering, atomising, spraying, spreading. The active products according to the invention can be applied both before and after the outbreak of the plants. They can also be incorporated, in the field before planting. The amount of active ingredient used can vary within wide limits. This depends fundamentally on the type of the desired effect. In general, the amounts applied are between 1 g and 10 kg of active product per hectare of land surface, preferably between 5 g and 5 kg per hectare. The preparation and use of the active compounds according to the invention are illustrated by means of the following examples.
Preparation examples: Example 1.
A mixture consisting of 2.1 g (5 mmol) of 1- (4-cyano-5-ethylsulfonylamino-2-fluoro-phenyl) -3-methyl-4-trifluoromethyl-3,6-dihydro-2,6-dioxo- is stirred. 1- (2H) -pyrimidine, 1.42 g (5 mmol) of 3- (3,4-dichloro-phenyl) propanoyl chloride, 0.63 g of triethylamine and 50 ml of acetonitrile for 3 hours at room temperature (approximately 20 ° C) ) and then concentrated by vacuum evaporation. the water trumpet The residue is taken up in chloroform and the crystalline product formed is isolated by suction filtration (fraction of product 1). The mother liquors are washed with IN hydrochloric acid and then with water, dried over sodium sulfate and filtered. The filtrate is concentrated by evaporation under vacuum of the water pump, the residue is digested with ethyl acetate and diethylether and the crystalline product formed is isolated by filtration by suction (fraction of product 2). The two product fractions are combined and stirred with 1N hydrochloric acid and with ethyl acetate. The aqueous phase is extracted twice with ethyl acetate, the combined organic phases are dried with sodium sulfate.
Sodium and filtered. The filtrate is concentrated by evaporation under vacuum of the water pump, the residue is digested with diethyl ether and the crystalline product formed is isolated by suction filtration. 1.3 g (42% of the theory) of the 1- [4-cyano-5- (N-ethylsul foni 1-N- (3- (3,4-dichlorophenyl) -propanoyl-ammonium) -2-fluoro-phenyl-3-methyl-4-trifluoride methyl-3,6-dihydro-2,6-dioxo-l (2H) -pyrimidine with a melting point of 205 ° C.
In a manner analogous to that of the preparation example 1, and also according to the general description of the preparation process according to the invention, the compounds of the formula (I) indicated in the following table 1 can also be prepared.
Table 1: Examples of compounds of the formula (I) ^^ g ^ - ^^^^^^^^^^ * ^^^^^^^^^ ' - * - '- ^ «*» 3st - »* r - -_ > ._, ^.-..., - M.
The following compounds can also be prepared analogously: Example No.71 Example No.72 Fp 191 ° C Application examples Example A. Pre-emergence test. Solvent: 5 parts by weight of acetone. Emulsifier: 1 Part by weight of alkylaryl polyglycol ether. To obtain a convenient preparation of active product, 1 part by weight of active compound is mixed with the indicated solvent amount, the amount of emulsifier indicated is added and the concentrate is diluted with water to the desired concentration. Seeds of the test plants are sown in normal soil. Approximately after 24 hours, the soil is irrigated with the preparation of active product, so that the desired amount of active product per unit area is applied respectively. The concentration of the sprayable broths will be chosen in such a way that the quantities of active product desired in each case are applied in 1000 liters of water per hectare. After three weeks, the degree of damage of the plants compared with the development of the untreated control is evaluated in%.
They mean: O% = no effect (same as untreated controls). 100% = total destruction. In this test, for example, the compound according to the preparation example 2 shows a very potent effect against weeds.
Example B. Post-emergence test. Solvent: 5 parts by weight of acetone. Emulsifier: 1 Part by weight of alkylaryl polyglycol ether. To obtain a suitable preparation of active compound, 1 part by weight of the active compound is mixed with the indicated amount of solvent, the amount of emulsifier indicated is added and the concentrate is diluted with water to the desired concentration. With the preparation of the active product, test plants are sprayed, having a height of 5 to 15 cm, so that in each case, the desired amounts of active product per unit area are applied. The concentration of And the sprayable products are chosen in such a way that the desired quantities of active product are applied in each case in 1000 liters of water / ha. After three weeks, the degree of damage of the plants is evaluated in% of damages compared to the development of the untreated controls. They mean: 0% = no effect (same as untreated controls) 100% = total destruction. In this test, for example, the compound according to the preparation example 2 shows a very potent effect against weeds. It is noted that in relation to this date, the best method known to the applicant to carry out the aforementioned invention, is that which is clear from the present description of the invention. Having described the invention as above, property is claimed as contained in the following:

Claims (8)

  1. R E I V I N D I C A C I O N S Substituted acylaminofinyl-uracils of the general formula (I) characterized in that n means the numbers 0 or 1, A means alkanediyl (alkylene) or cycloalkanediyl respectively substituted, or - provided that when n means 1- it also means a single bond or is bridged with Ar through a "alkanediyl" group, "Ar" means aryl, arylalkyl, heterocyclyl or heterocyclylalkyl, respectively substituted if appropriate, means O (oxygen), S (sulfur), SO, S02, NH or N (alkyl), R1 means hydrogen, amino or optionally substituted alkyl, R2 means carboxy, cyano, carbamoyl, thiocarbamoyl or means alkyl or alkoxycarbonyl respectively substituted, where R3 signifies hydrogen, halogen or optionally substituted alkyl R4 means hydrogen, cyano, carbamoyl, thiocarbamoyl or halogen, R5 means cyano, carbamoyl, thiocarbamoyl, halogen or means alkyl or alkoxy substituted respectively, and R6 signifies hydrogen or means alkyl, alkylcarbonyl, alkoxycarbonyl, alkylsulfonyl, alkenyl, alkenylcarbonyl , alkenylsulfonyl, alkynyl, cycloalkylcarbonyl, cycloalkylsulfonyl, arylcarbonyl, arylsulfonyl, arylalkylcarbonyl, arylalkylsulfonyl, heterocyclylcarbonyl or heterocyclylsulfonyl respectively substituted, if appropriate. . ^. Jafe • "- '• - - -" "• -« ÉMUMMAü? L.
  2. 2. Substituted acylaminophenyl-uracils according to claim 1, characterized in that n means the numbers 0 or 1, A means alkanediyl (alkylene) with 1 to 6 carbon atoms or cycloalkanediyl with 3 a 6 carbon atoms, respectively substituted by halogen or -in the case where n means 1- also means a single bond or is linked to Ar through an encapsulated ring with 1 to
  3. 3 carbon atoms, Ar means aryl or arylalkyl respectively substituted, respectively, with 6 or 10 carbon atoms in the aryl group and, optionally, 1 to 4 carbon atoms in the alkyl part, or substituted heterocyclyl or heterocyclylalkyl respectively optionally with 1 to 5 carbon atoms and at least one heteroatom (up to 4 nitrogen atoms and / or optionally 1 or 2 oxygen or sulfur atoms), it being possible to take the respective substituents, preferably from the following enumeration: nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, alkyl with 1 to 4 carbon atoms, halogen with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, halogenalkoxy with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms, halogenalkylthio with 1 to 4 carbon atoms, alkylsulfinyl with 1 to 4 carbon atoms, haloalkylsulfinyl with 1 to 4 carbon atoms, alkylsulfonyl with 1 to 4 carbon atoms, halogenoalkylsulfonyl with 1 to 4 carbon atoms, alkylamino with 1 to 4 carbon atoms, di- (alkyl with 1 to 4 carbon atoms) -amino, alkylcarbonyl with 1 to 4 carbon atoms , alkoxycarbonyl with 1 to 4 carbon atoms, alkylaminocarbonyl with 1 to 4 carbon atoms, di- (alkylamino with 1 to 4 carbon atoms) - aminocarbonyl, di- (alkyl with 1 to 4 carbon atoms) -amino -sulfonyl, Q means O (oxygen), S (sulfur), SO, S02, NH or N (alkyl having 1 to 4 carbon atoms), 1 means hydrogen, amino or alkyl with 1 to 6 carbon atoms substituted in case given by cyano, by carboxy, by halogen, by alkoxy with 1 to 4 carbon atoms or by alkoxy-carbonyl with 1 to 4 carbon atoms, R2 means carboxy, cyano, carbamoyl, thiocarbamoyl or means alkyl or alkoxycarbonyl respectively 6 carbon atoms in the alkyl groups substituted respectively by cyano , by halogen or by alkoxy having 1 to 4 carbon atoms, R3 is hydrogen, halogen or alkyl having 1 to 6 carbon atoms, optionally substituted by halogen, R4 is hydrogen, cyano, carbamoyl, thiocarbamoyl, fluorine or chlorine, R5 means cyano, carbamoyl, thiocarbamoyl, halogen or means alkyl or alkoxy with 1 to 4 carbon atoms respectively, optionally substituted by halogen, and R6 is hydrogen, means alkyl, alkylcarbonyl or alkoxycarbonyl having 1 to 6 carbon atoms, respectively in The alkyl groups, each substituted, if appropriate, by cyano, by halogen, or by alkoxy with 1 to 4 carbon atoms, means alkylsulfonyl having 1 to 6 carbon atoms. optionally substituted by halogen means alkenyl, alkenylcarbonyl, alkenylsul fonyl or alkynyl with, respectively, up to 6 carbon atoms, respectively substituted by halogen, means cycloalkylcarbonyl or cycloalkylsul fonyl with 3 to 6 carbon atoms in each cycloalkyl group, Where appropriate substituted by halogen, it means arylcarbonyl, arylsulfonyl, arylalkylcarbonyl or arylalkylsulfonyl having 6 or 10 carbon atoms in the aryl groups and optionally 1 to 4 carbon atoms in the alkyl part, respectively substituted by nitro, if appropriate , by cyano, by halogen, by alkyl with 1 to 4 carbon atoms, by halogenalkyl with 1 to 4 carbon atoms, by alkoxy n 1 to 4 carbon atoms, by halogenalkoxy with 1 a ÜS -.-. ^ .- ^ .. * - - - - - ^ .. ^. ^^ .- ..? - t. ^. ^ * - 4 carbon atoms, eg alkylthio with 1 a 4 carbon atoms, by halogenalkylthio with 1 to 4 carbon atoms, by alkylsulfinyl with 1 to 4 carbon atoms, by halogenalkylsulfonyl with 1 to 4 carbon atoms, by alkylsulfonyl with 1 to 4 carbon atoms, by haloalkylsulfonyl with 1 to 4 carbon atoms, for alkylcarbonyl with 1 to 4 carbon atoms, for alkoxycarbonyl with 1 10 to 4 carbon atoms or by di- (C 1 -C 4 alkylamino) -sulfonyl, or means heterocyclylcarbonyl or heterocyclylsulfonyl with 1 to 5 carbon atoms and 1 to 4 nitrogen atoms and / or 1 or 2 carbon atoms Oxygen or sulfur, respectively substituted, if appropriate, by nitro, by cyano, by halogen, by alkyl with 1 to 4 carbon atoms, by halogenalkyl with 1 to 4 carbon atoms, by alkoxy with 1 to 4 carbon atoms; 20 carbon, for halogenalkoxy with 1 to 4 carbon atoms, for alkylthio with 1 to 4 carbon atoms, for halogenalkylthio with 1 to 4 carbon atoms, for alkylsulfinyl with 1 to 4 carbon atoms, for ^ jj ^ a * ^ iú? uai ¿¿. haloalkyl sulphonyl with 1 to 4 carbon atoms, for alkylsulphonyl with 1 to 4 carbon atoms, for halogenalkylsulphonyl with 1 to 4 carbon atoms, for alkylcarbonyl with 1 to 4 carbon atoms, for alkoxycarbonyl with 1 to 4 carbon atoms or by di- (alkyl-amino with 1 to 4 carbon atoms) -sulphonyl. 3. Substituted acylaminofenyl uracils according to claim 1, characterized in that n denotes the numbers 0 or 1, A means methylene, ethane-1, 1-diyl (ethylidene), ethane-1,2-diyl (dimethylene), propane- 1, 1-diyl (propylidene), propane-1,2-diyl or propane-1,3-diyl (trimethylene), cyclopropane-1,1-diyl, cyclopropane-1,2-diyl, cyclobutane-1,1-diyl, cyclopentane-1 , 1-diyl or cyclohexane-1,1-diyl respectively substituted, if appropriate, by fluorine and / or chlorine, or means - in the case where n means 1 - also a single bond, or is linked to Ar through a 1,2-ethanediyl group (dimethylene), Ar means phenyl, naphthyl, benzyl, 1-phenylethyl, 2-f-ethyl, l-enyl-propyl, MMHüiM ^ kB ^. ^^ m ^ ¡AaaMeiig ^ lw 2-phenyl-propyl or 3-phenyl-propyl respectively substituted, or means heterocyclyl or heterocyclylalkyl, respectively substituted, if appropriate, from the series consisting of oxiranyl, oxiranylmethyl, oxetanyl , oxetanilmetilo, furyl, furylmethyl, tetrahydrofuryl, tetrahydrofurylmethyl, thienyl, thienylmethyl, tetrahydrothienyl, tetrahydrothienylmethyl, benzofuryl, benzofurilmetilo, dihydro-benzofuryl, dihidrobenzofurilmetilo, benzothienyl, benzothienylmethyl, pyrrolyl, pyrrolylmethyl, pyrazolyl, pyrazolylmethyl, pyranyl, piranilmetilo, benzopyranyl, benzopiranilmetilo, dihydrobenzopyranyl , dihydrobenzopyranylmethyl, tetrahydrobenzo-pharanyl, tetrahydrobenzopyranylmethyl, pyridinyl, pyridinylmethyl, pyrimidinyl, pyrimidinylmethyl, the respective substituents being preferably taken from the following enumeration: nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, SM.sub.4 &.sup.-4 .- ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, n- , i-, s- or t-butoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, n- or i- propylsulfinyl, trifluoromethyl sulfate, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, trifluoromethylsulphonyl, methylamino, ethylamino, n- or i-propylamino, n-,? -, s- or t-butylamino, dimethylamino, diethylamino, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl, dimethylaminosulfonyl, diethylaminosulfonyl. Q means 0 (oxygen), S (sulfur), SO, S02, NH or N (methyl), R1 means hydrogen, amino or methyl or ethyl substituted respectively by cyano, fluorine, chlorine, methoxy or ethoxy, R 'means carboxy, cyano, carbamoyl, thiocarbamoyl or means methyl, ethyl, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl respectively substituted where appropriate by cyano, fluorine, chlorine, methoxy or ethoxy, R3 means hydrogen, fluorine, chlorine, bromine or methyl, ethyl, n- or i-propyl respectively substituted, if appropriate, by fluorine and / or chlorine, R4 means hydrogen, fluorine or chlorine, cyano, carbamoyl and thiocarbamoyl R5 means cyano, Carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or means methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy substituted respectively by fluorine and / or by chlorine, R6 means hydrogen, means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, acetyl, propionyl, n- or i-bu thyroyl, n-, i-, or sec. -valeryl, pivaloyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl respectively substituted, if appropriate, by cyano, fluorine, chlorine, methoxy or ethoxy, means methanesulfonyl, ethylsulfonyl, non-propylsulfonyl, n-, i- , s- or t-butylsulfonyl, respectively substituted by fluorine and / or chlorine, respectively, means ethenyl, propenyl, butenyl, ethenylcarbonyl, propanylcarbonyl, butenylcarbonyl, ethynyl, propynyl, or butynyl substituted, respectively, by fluorine, by chlorine and / or bromine, means cyclopropylcarbonyl, ciclopropilmet i Icarboni it, cyclobutyl-carbonyl, ciclobutilmetilcarbonilo, cyclopentylcarbonyl, ciclopentilmetilcar-bonilo, cyclohexylcarbonyl, cyclohexylmethylcarbonyl, cyclopropyl-sulfonyl, cyclopropyl-methylsulfonyl, ciclobutilmetilsulfonilo, ciclopentilsul-fonilo, cyclopentyl-methylsulfonyl, cyclohexylsulfonyl and cyclohexylmethyl -sulfonyl substituted, where appropriate, by fluorine, by chlorine and / or or bromine, ^^ feasaj-j ^ .. means benzoyl, phenylsulfonyl, phenylacetyl, phenylpropionyl, benzylsulphonyl, or phenylethylsulfonyl respectively substituted, where appropriate, by nitro, by cyano, by fluorine, by chlorine, by bromine, by methyl, by ethyl, by n- or 1-propyl, n- , i-, s- or t-butyl, by trifluoromethyl, by methoxy, by ethoxy, by n- or i-propoxy, by n-, i-, s- or t-butoxy, by difluoromethoxy, by trifluoromethoxy, by methylthio , by ethylthio, by n- or i-propylthio, by n-, i-, s- or t-butylthio, by difluoromethylthio, by trifluoromethylthio, by methylsulfinyl, by ethylsulfinyl, by n- or i-propylsulfinyl, by trifluoromethyl - sulfinyl, by methanesulfonyl, by ethylsulphonyl, by n- or i-propylsulfonyl, by trifluoromethylsulphonyl, by acetyl, by propionyl, by n- or i-butyroyl, by methoxycarbonyl, by ethoxycarbonyl, by n- or i-propoxycarbonyl, by dimethylaminosulfonyl or by dialkylaminosulfonyl, or means heterocyclylcarbonyl or heterocyclylsul fonyl of the formed series by furylcarbonyl, furylsulfonyl, thienylcarbonyl, thienylsulfonyl, pyrazolylcarbonyl, pyrazolysulfonyl, pyridinylcarbonyl, pyridinylsulfonyl, quinolinylcarbonyl, quinolinylsulfonyl, pyrimidylcarbonyl, pyrimidinylsulfonyl, each optionally substituted by nitro, by cyano, by fluorine, by chlorine, by bromine, by methyl, by ethyl, by n- or i-propyl, by n-, i-, s- or t-butyl , by trifluoromethyl, by methoxy, by ethoxy, by n- or i-propoxy, by n-, i-, s- or t-butoxy, by di-fluoromethoxy, by trifluoromethoxy, by methylthio, by ethylthio, by n- or -propylthio, by n-, s- or t-butylthio, by difluoromethylthio, by trifluoromethylthio, by methylsulfinyl, by ethylsulfinyl, by n- or i-propylsulfinyl, by trifluoromethyl-sulphonyl, by methylsulfonyl, by ethylsulphonyl, by n- or i-propylsulfonyl , by trifluoromethylsulfonyl, by acetyl, by propionyl, by n- or i-butyroyl, by methoxycarbonyl, by ethoxycarbonyl, by n-
  4. 4) Substituted acylaminophenyl-uracils according to claim 1, characterized in that n denotes the amount of substituted acylaminophenyl-uracils according to claim 1. number 1, A means methylene, ethane-1, 1-diol (ethylidene) or ethane-1,2-diyl (dimethylene), Ar means phenyl, naphthyl or benzyl respectively substituted, it being possible to take the respective substituents, especially from the following enumeration: nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i- propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulphinyl, n- or i-propylsulfinyl, trifluoromethyl-sulphonyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, trifluoromethyl-sulphonyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, Q means O (oxygen), R 1 signifies hydrogen, amino or methyl, R 2 signifies trifluoromethyl, RJ signifies hydrogen, chlorine or methyl, R 4 signifies hydrogen, fluorine or chlorine, R 5 signifies cyano, carbamoyl, thiocarbamoyl, chlorine or bromine, R 6 signifies hydrogen, means methanesulfonyl , ethylsulphonyl, n- or i-propylsulphonyl, n-, i-, s- or t-butylsulfonyl, respectively substituted, if appropriate, by fluorine and / or by chlorine, or means cyclopropylsulfonyl respectively substituted, if appropriate, by fluorine and / or by chlorine .
  5. 5. Substituted acylaminofenyl-uracils according to claim 1, characterized in that n means number 0, A means methylene, ethane-1, 1-diyl (ethylidene) or ethane-1,2-diyl (dimethylene), Ar means phenyl, naphthyl or benzyl substituted respectively where appropriate, it being possible to take the respective substituents, especially from the following enumeration: nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n- , i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i- propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfyl, ethylsulphyl, n- or i- propylsulfinyl, trifluoromethyl ilsulphyl, methylsulfonyl, ethylsulphyl, n- or i-propylsulphonyl, trifluoromulphsulfoyl, methoxycarbonyl, ethoxycarbonyl, n- or i- propoxycarbonyl, Rl means hydrogen, amino or methyl, R 2 is trifluoromethyl, RJ is hydrogen, chlorine or methyl, R 4 is hydrogen, fluorine or chlorine, R 5 is cyano, carbamoyl, thiocarbamoyl, chlorine or bromine, R 6 is hydrogen, means methanesulfonyl, ethylsulfonyl, n- or i-propylsulfonyl , n-, i-, s- or t-butils ulphonyl, respectively substituted, if appropriate, by fluorine and / or by chlorine, or means cyclopropylsulfonyl substituted respectively by fluorine and / or by chlorine. ^^^^^ fc ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ 2 ^^^^^^^ | ^^^ faith
  6. 6. Process for obtaining the substituted acylaminophenyl-uracils according to one of claims 1 to 5, characterized in that aminophenyl-uracils of the general formula (II) are reacted wherein R1, R2, R3, R4, R5 and R6 have the meaning indicated above, with acylating agents of the general formula (III), x? NQ) '"Ar (lll) O in which _ *: Jit 5A. -n, A, Ar and Q have the meaning indicated in one of claims 1 to 5, and X means halogen, if appropriate in the presence of an auxiliary agent of the reaction and, if appropriate, in the presence of a diluent, and, if appropriate, electrophilic or nucleophilic reactions or oxidation or reduction reactions are usually carried out in the context of the definition of the substituents.
  7. 7. Use of at least one acylaminophenol-substituted uracil according to one of claims 1 to 5, for the control of undesirable plants.
  8. 8. Herbicidal agents, characterized in that they have a content of at least one substituted acylaminophenyl-uracil according to one of claims 1 to 5, and customary extenders. .? ,,. .. ... - ... i ...,.-.-...- ^ ,, -.-_. "," ^, - "Aa ^^ aafefca .. ^ - t ^ i ^ ------ ^ .-, - ^. ^^ M.-
MXPA/A/2001/000207A 1998-07-09 2001-01-08 Substituted acylamino phenyl uracils MXPA01000207A (en)

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Application Number Priority Date Filing Date Title
DE19830694.6 1998-07-09

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MXPA01000207A true MXPA01000207A (en) 2001-11-21

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