MXPA99005618A - Heterocyclyluracil - Google Patents

Heterocyclyluracil

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Publication number
MXPA99005618A
MXPA99005618A MXPA/A/1999/005618A MX9905618A MXPA99005618A MX PA99005618 A MXPA99005618 A MX PA99005618A MX 9905618 A MX9905618 A MX 9905618A MX PA99005618 A MXPA99005618 A MX PA99005618A
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MX
Mexico
Prior art keywords
carbon atoms
atoms
alkyl
halogen
alkylsulfonyl
Prior art date
Application number
MXPA/A/1999/005618A
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Spanish (es)
Inventor
Wilhelm Drewes Mark
Haas Wilhelm
Dollinger Markus
Andree Roland
Original Assignee
Bayer Ag 51373 Leverkusen De
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Publication of MXPA99005618A publication Critical patent/MXPA99005618A/en

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Abstract

The invention relates to novel heterocyclyluracil of formula (I), wherein R1, R2, R3 and Het have the meanings cited in the description. The invention also relates to a method for the production of these substances and the use thereof as herbicides.

Description

HETEROCICLILURACILOS Description of the invention: The present invention relates to new heterocyclyluracils, various processes for their preparation and their use as herbicides. A large number of heterocyclyluracils with herbicidal or insecticidal properties have already been disclosed (see JP-A 91-287 585, JP-A 93 202 031, Chem. Abstr. 116, 235 650 and Chem. Abstr.120, 107 408). Thus, for example, l- (3-chloro-5-trifluoromethylpyridin-2-yl) -3,6-dihydro-2,6-dioxo-4-trifluoromethyl-1 (2H) -pyrimidine can be used for the control against weeds. However, due to low application quantities, the activity of this product is not always satisfactory. New heterocyclyluracils of the formula (I) have now been found wherein R 1 signifies hydrogen or means alkyl having 1 to 4 carbon atoms, optionally substituted by cyano, by halogen or by alkoxy with 1 to 4 carbon atoms, R2 means formyl, hydroxyiminomethyl, cyano, carboxy, alkoxycarbonyl, carbamoyl, thiocarbamoyl or means alkyl having 1 to 4 carbon atoms, optionally substituted by halogen, R3 means hydrogen, cyano, halogen or means alkyl having 1 to 4 carbon atoms substituted if provided by halogen and Het means the rest of the formula where R 4 signifies hydroxy, mercapto, amino, nitro, cyano, carbamoyl, thiocarbamoyl, alkoxyalkyl with 1 to 4 carbon atoms in the alkoxy part and 1 to 6 carbon atoms in the alkyl part, alkoxy with 1 to 6 carbon atoms, halogenalkoxy with 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkoxyalkoxy with 1 to 6 carbon atoms in each part alkoxy, alkylthio with 1 to 6 carbon atoms, halogenalkylthio with 1 to 6 carbon atoms and 5 carbon atoms halogen, alkylsulfinyl with 1 to 6 carbon atoms, haloalkylsulfonyl with 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkylsulfonyl with 1 to 6 carbon atoms, halogenoalkylsulfonyl with 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkylcarbonyl with 1 to 6 carbon atoms in the alkyl part, halogen-alkylcarbonyl with 1 to 5 halogen atoms and 6 carbon atoms in the haloalkyl part, alkoxycarbonyl with 1 to 6 carbon atoms in the part alkoxy, h alkoalkoxycarbonyl with 1 to 5 ha-halogen atoms and 1 to 6 carbon atoms in the halogeno-alkoxy part, alkylamino with 1 to 6 carbon atoms, dialkylamino with 1 to 6 carbon atoms in each alkyl part, haloalkylamino with 1 to 5 halogen atoms and 1 to 6 carbon atoms, alkylaminocarbonyl with 1 to 6 carbon atoms in the alkyl part, dialkylaminocarbonyl with 1 to 6 carbon atoms in each alkyl part, alkylsulfonylate with 1 to 6 carbon atoms in the alkyl, halogenoalkylsulfonyl-amino part having 1 to 5 halogen atoms and 1 to 6 carbon atoms in the haloalkyl part, N, N-bis-alkyl-sulfonylate having 1 to 6 carbon atoms in each alkyl part, N, N-bis-halogenoalkylsulfonyl-amino with 1 to 5 halogen atoms and 1 to 6 carbon atoms in each halloalkyl part, N-alkyl-N-alkylsulfonyl-amino with 1 to 6 carbon atoms in the alkyl part and 1 to 6 carbon atoms in the alkylsulfonyl part, N-haloalkyl- N-halogenoalkylsulfonyl-amino with 1 to 5 halogen atoms and 1 to 6 carbon atoms in the haloalkyl part and 1 to 5 halogen atoms and 1 to 6 carbon atoms in the halogenoalkylsulfo-nyl part, N-alkylcarbonyl-N- alkylsulfonyl-amino with 1 to 6 carbon atoms in the alkyl part of the alkylcarbonyl group and 1 to 6 carbon atoms in the part alkylsulfonyl, N-halogenoalkylcarbonyl-N-halogeno-alkylsulfonyl-amino with 1 to 5 halogen atoms and 6 atoms carbon in the halogenoalkyl part and 1 to 5 halogen atoms and 1 to 6 carbon atoms in the halogenoalkylsulfonyl part or means N-alkyl-sulfonyl-N-phenylcarbonyl-amino with 1 to 6 carbon atoms in the alkylsulfonyl part, substituted if given one to three times, in the same or in different forms by halogen, by alkyl with 1 to 4 carbon atoms, by dialkylamino with 1 to 4 carbon atoms in each alkyl group and / or by alkoxy with 1 to 4 carbon atoms, ignites hydroxy, mercapto, amino, nitro, cyano, carboxy, carbamoyl, halogen, alkyl having 1 to 6 carbon atoms, thiocarbamoyl, alkoxyalkyl with 1 to 4 carbon atoms in the alkoxy part and 1 to 6 carbon atoms in the alkyl part, alkoxy with 1 to 6 carbon atoms, alkoalkoxy with 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkoxyalkoxy with 1 to 6 carbon atoms in each part alkoxy, alkylthio with 1 to 6 carbon atoms, halogenalkylthio with 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkylsulfinyl with 1 to 6 carbon atoms, haloalkyl sulfinyl with 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkylsulfonyl with 1 to 6 carbon atoms, haloalkylsulfonyl with 1 to 6 carbon atoms and 1 to 5 carbon atoms halogen, alkylcarbonyl having 1 to 6 carbon atoms in the alkyl part, halogeno-noalkylcarbonyl having 1 to 5 halogen atoms and 1 to 6 carbon atoms in the haloalkyl part, alkoxycarbonyl having 1 to 6 carbon atoms in the alkoxy part, haloalkoxycarbonyl with 1 to 5 halogen atoms and 1 to 6 carbon atoms in the halogenoalkoxy part, alkylamino with 1 to 6 carbon atoms, dialkylamino with 1 to 6 carbon atoms in each alkyl part, haloalkylamino with 1 to 5 halogen atoms and 1 to 6 carbon atoms, alkylaminocarbonyl with 1 to 6 carbon atoms in the alkyl part, dialkylaminocarbonyl with 1 to 6 carbon atoms in each alkyl part, alkylsulphonylate with 1 to 6 carbon atoms in each alkyl part, haloalkyl sulfonylamino having 1 to 5 halogen atoms and 1 to 6 carbon atoms in the haloalkyl part, N, N-bis-alkyl-sulfonylamino having 1 to 6 carbon atoms in each alkyl part, N, N-bis-halogenoalkylsulf onyl-amino with 1 to 5 halogen atoms and 1 to 6 carbon atoms in each halloalkyl part, N-alkyl-N-alkylsulfonyl-amino with 1 to 6 carbon atoms in the alkyl part and 1 to 6 carbon atoms in the alkylsulfonyl part N-halogenoalkyl-N-halogenoalkylsulfonyl-amino with 1 to 5 halogen atoms and 1 to 6 carbon atoms in the halogenoalkyl part and 1 to 5 halogen atoms and 1 to 6 carbon atoms in the halogenoalkylsulfo-nyl part , N-alkylcarbonyl-N-alkylsulfonyl-amino with 1 to 6 carbon atoms in the alkyl part of the alkylcarbonyl group and 1 to 6 carbon atoms in the alkylsulfonyl part, N-halogenoalkylcarbonyl-N-halogeno-alkylsulfonyl-amino with 1 to 5 halogen atoms and 1 to 6 carbon atoms in the halogenoalkyl part and 1 to 5 halogen atoms and 1 to 6 carbon atoms in the halogenoalkylsulfonyl part or means N-alkylsul-fonyl-N-phenylcarbonyl-amino with 1 to 6 carbon atoms in the substituted alkylsulfonyl part optionally from one to three times, in the same or different manner by halogen, by alkyl with 1 to 4 carbon atoms, by dialkylamino with 1 to 4 carbon atoms in each alkyl group and / or by alkoxy with 1 to 4 carbon atoms, and means integers from 0 to 3, or Het means the rest of the formula where R 6 signifies hydroxy, mercapto, amino, carboxy, carbamoyl, thiocarbamoyl, alkoxyalkyl with 1 to 4 carbon atoms in the alkoxy part and 1 to 6 carbon atoms in the alkyl part, alkoxy with 1 to 6 carbon atoms, haloalkoxy with 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkoxyalkoxy with 1 to 6 carbon atoms in each part alkoxy, alkylthio with 1 to 6 carbon atoms, halogenalkylthio with 1 to 6 carbon atoms and 1 to 5 carbon atoms halogen, alkylsulfinyl with 1 to 6 carbon atoms, halogenoalkylsulfinyl with 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkylsulfonyl with 1 to 6 carbon atoms, haloalkylsulfinyl with 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkylcarbonyl with 12 to 6 carbon atoms in the alkyl part, haloalkylcarbonyl with 1 to 5 halogen atoms and 1 to 3 carbon atoms in the halogenoalkyl part, alkoxycarbonyl with 1 to 6 carbon atoms in the part alkoxy, ha-ló genoalkoxycarbonyl with 1 to 5 halogen atoms and 1 to 6 carbon atoms in the halogenoalkoxy part, alkylamino with 6 carbon atoms, dialkylamino with 1 to 6 carbon atoms in each alkyl part, ha-linoalkylamino with 1 to 5 carbon atoms halogen and 1 to 6 carbon atoms, alkylaminocarbonyl with 1 to 6 carbon atoms in the alkyl part, dialkylaminocarbonyl with 1 to 6 carbon atoms in each alkyl part, alkylsulfonylamino with 1 to 6 carbon atoms in the alkyl part, haloalkyl sulfonylamino having 1 to 5 halogen atoms and 1 to 6 carbon atoms in the halogenoalkyl part, N, N-bis-alkylsulfo-nylamino having 1 to 6 carbon atoms in each alkyl part, N, N-bis-halogenoalkylsulfonyl-amino with 1 to 5 halogen atoms and 1 to 6 carbon atoms in each halogenoalkyl part, N-alkyl-N-alkylsulfonyl-amino with 1 to 6 carbon atoms in the alkyl part and 1 to 6 carbon atoms in the alkylsulfonyl part , N-ha-loloalkyl-N-hal Oxyalkylsulfonyl-amino with 1 to 5 halogen atoms and 1 to 6 carbon atoms in the halogenoalkyl part and 1 to 5 halogen atoms and 1 to 6 carbon atoms in the halogenoalkylsulfonyl part, N-alkylcarbonyl-N-alkylsulfonyl amino with 1 to 6 carbon atoms in the alkyl part of the alkylcarbonyl group and 1 to 6 carbon atoms in the alkylsulfonyl part, N-halogenoalkylcarbonyl-N-halogeno-alkylsulfonyl-a with 1 to 5 halogen atoms and to 6 carbon atoms. carbon in the halogenoalkyl part and to 5 halogen atoms and 1 to 6 carbon atoms in the halogenoalkylsulfonyl part or means N-alkylsul-fonyl-N-phenylcarbonylamino with 1 to 6 carbon atoms in the alkylsulfonyl part, substituted one to three times in the same or different ways by halogen, by alkyl with 1 to 4 carbon atoms, by dialkylamino with 1 to 4 carbon atoms in each alkyl group and / or by alkoxy with 1 to 4 carbon atoms, ignites hydroxy, mercapto , to me no, cyano, nitro, car-boxi, carbamoyl, thiocarbamoyl, halogen, alkyl having 1 to 6 carbon atoms, alkoxyalkyl with 1 to 4 carbon atoms in the alkoxy part and 1 to 6 carbon atoms in the alkyl part, alkoxy with 1 to 6 carbon atoms, haloalkoxy with 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkoxyalkoxy with 1 to 6 carbon atoms in each part alkoxy, alkylthio with 1 to 6 carbon atoms, halogenalkylthio with 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkylsulfinyl with 1 to 6 carbon atoms, haloalkyl sulfinyl with 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkylsulfonyl with 1 to 6 carbon atoms, haloalkylsulfonyl with 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkylcarbonyl with 1 to 6 carbon atoms in the alkyl part, halogenalkylsulfonyl with 1 to 5 halogen atoms and 1 to 6 carbon atoms in the haloalkyl part, alkoxycarbonyl with 1 to 6 carbon atoms in the part alkoxy, halogenoalkoxycarbonyl with 1 to 5 halogen atoms and 1 to 6 carbon atoms in the halogen-alkoxy part, alkylamino with 1 to 6 carbon atoms, dialkylamino with 1 to 6 carbon atoms in each alkyl part, haloalkylamino with 1 to 5 halogen atoms and 1 to 6 carbon atoms, alkylaminocarbonyl with 1 to 6 carbon atoms in the alkyl, di-alkylaminocarbonyl having 1 to 6 carbon atoms in each alkyl part, alkylsulphonyl with 1 to 6 carbon atoms in the alkyl part, haloalkylsulphonylamino having 1 to 5 halogen atoms and 1 to 6 carbon atoms in the Halogenoalkyl part, N, N-bis-alkylsulphonylate with 1 to 6 carbon atoms in each alkyl part, N, N-bis-halogenoalkylsulfonyl-amino with 1 to 5 halogen atoms and 1 to 6 carbon atoms in each haloalkyl part, N-alkyl-N-alkylsulfo-nil-amino with 1 to 6 carbon atoms in the alkyl part and 1 to 6 carbon atoms in the alkylsulphonyl part, N-haloalkyl-N-halogenoalkylsulfonyl-amino with 1 to 5 halogen atoms and 1 to 6 carbon atoms in the hal genoalkyl and 1 to 5 halogen atoms and 1 to 6 carbon atoms in the part halogenalkylsulfonyl, N-alkylcarbonyl-N-alkylsulfonyl amino with 1 to 6 carbon atoms in the alkyl part of the alkylcarbonyl group and 1 to 6 atoms of carbon in the part alkylsulfonyl, N-halogenoalkylcarbonyl-N-halogenoalkylsulfonyl-amino with 1 to 5 halogen atoms and 1 to 6 carbon atoms in the haloalkyl part and 1 to 5 halogen atoms and 1 to 6 carbon atoms in the Halogenoalkylsulfonyl part or means N-alkylsulfonyl-N-phenylcarbonyl-amino having from 1 to 6 carbon atoms in the alkylsulfonyl part, optionally substituted from one to three times, in the same way 0 in different ways by halogen, by alkyl with 1 to 4 carbon atoms, by dialkylamino with 1 to 4 carbon atoms in each alkyl group and / or by alkoxy with 1 to 4 carbon atoms, and n means integers from 0 to 3, or Het means the rest of the formula where R8 signifies hydrogen, halogen, cyano, alkyl having 1 to 6 carbon atoms, halogenalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms or means nitro and R9 means amino, alkylamino having 1 to 6 carbon atoms, dialkylamino with 1 to 6 carbon atoms in each alkyl part, haloalkylamino with 1 to 5 halogen atoms and 1 to 6 carbon atoms, alkylaminocarbonyl with 1 to 6 carbon atoms in the alkyl part, dialkylaminocarbonyl with 1 to 6 carbon atoms in each alkyl part, alkylsulfonylamino with 1 to 6 carbon atoms in the alkyl part, halogenoalkylsulfonylamino with 1 to 5 halogen atoms and 1 to 6 carbon atoms in the haloalkyl part, N, N-bis-alkylsulfonylamino with 1 to 6 carbon atoms in each alkyl part, N, N-bis-halogenoalkylsulfonyl-amino with 1 to 5 halogen atoms and 1 to 6 carbon atoms in each haloalkyl part, N-alkyl-N-alkylsulfonyl- amino with 1 to 6 carbon atoms or in the alkyl part and 1 to 6 carbon atoms in the part alkylsulfonyl, N-haloalkyl-N-haloalkylsulphonyl-amino with 1 to 5 halogen atoms and 1 to 6 carbon atoms in the haloalkyl part and 1 to 5 halogen atoms and 1 to 6 carbon atoms in the halogenoalkylsulfonyl part, N-alkylcarbonyl-N-alkylsulfonyl-amino with 1 to 6 carbon atoms in the alkyl part of the alkylcarbonyl group and 1 to 6 carbon atoms in the part alkylsulfonyl, N-haloalkylcarbonyl-N-halogenoalkylsulfonyl-amino with 1 to 5 halogen atoms and 1 to 6 carbon atoms in the haloalkyl part and 1 to 5 halogen atoms and 6 carbon atoms in the halogenoalkylsulphonyl part or means N-alkylsulfonyl-N-phenylcarbonyl amine with 1 to 6 carbon atoms in the alkylsulfonyl part, optionally substituted one to three times, in the same or different ways by halogen, by alkyl with 1 to 4 carbon atoms, by dialkylamino with 1 to 4 carbon atoms in each alkyl group and / or alkoxy with 1 to 4 carbon atoms. It has also been found that the heterocyclyluracils of the formula (I) are obtained if a) aminoalkenoic acid esters of the formula are reacted wherein R 2 and R 3 have the meanings indicated above, R 10 signifies hydrogen or alkyl having 1 to 4 carbon atoms and R means alkyl, aryl or arylalkyl, or a) with heterocyclylisocyanate of the formula 0 = C = N-Het (III ) in which Het has the meaning indicated above, or ß) with heterocyclic carbamates of the formula H R'O. . (IV) And Het wherein Het has the meaning indicated above and R 11 means alkyl, aryl, or arylalkyl, respectively, optionally in the presence of an acid-binding agent and, if appropriate, in the presence of a diluent, b) heterocyclyluracils of the formula are reacted wherein R2, R3 and Het have the meanings given above, either a) with halogen-compounds of the formula R12-Hal (V) in which R12 means alkyl having 1 to 4 carbon atoms, optionally substituted by cyano, by halogen or by alkoxy with 1 to 4 carbon atoms and Hal means chlorine, bromine or iodine, ß) with dialkyl sulfates of the formula wherein R13 means alkyl having 1 to 4 carbon atoms, respectively, if appropriate in the presence of an acid-binding agent and, if appropriate, in the presence of a diluent. Finally, it has been found that the new heterocyclyluracils of the formula (I) have very good herbicidal properties. Surprisingly, the heterocyclyluracils according to the invention of the formula (I) have a substantially better herbicidal activity than the previously known active compounds., closer from the point of view of its constitution, with the same activity address. In the present case, alkyl, alkoxy, alkylthio, alkylamino, dialkylamino, haloalkyl, haloalkoxy and haloalkylthio are understood to be straight chain or branched chain residues respectively. In the present case halogen means -when not otherwise said- fluorine, chlorine, bromine or iodine. The heterocyclyluracils according to the invention are generally defined by the formula (I). preferred are compounds of the formula (I), in which R 1 is hydrogen or is alkyl having from 1 to 3 carbon atoms, optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, R 2 represents formyl, hydroxyiminomethyl, cyano, carboxy, alkoxycarbonyl having 1 to 4 carbon atoms in the part alkoxy, carbamoyl, thiocarbamoyl or means alkyl having 1 to 3 carbon atoms, optionally substituted one to three times, in the same or in different ways by fluorine and / or chlorine, R3 means hydrogen, cyano, fluorine, chlorine or means alkyl with 1 to 3 carbon atoms, optionally substituted one to three times, in the same or different ways by fluorine and / or chlorine and Het means the rest of the formula where R 4 signifies hydroxy, mercapto, amino, cyano, nitro, carboxy, carbamoyl, thiocarbamoyl, alkoxyalkyl with 4 carbon atoms in the alkyl part and 1 or 2 carbon atoms in the alkoxy part, alkoxy with 1 to 4 atoms carbon, haloalkoxy with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms, alkoxyalkoxy with 1 to 4 carbon atoms in each alkoxy part, alkylthio with 1 to 4 carbon atoms, haloalkylthio 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms, alkylsulfinyl with 1 to 4 carbon atoms, haloalkylsulfinyl with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms, alkylsulfonyl with 1 to 4 carbon atoms, halogenoalkylsulfonyl with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms, alkylcarbonyl with 1 to 4 carbon atoms in the alkyl part, haloalkylcarbonyl with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms in the haloalkyl part, alco xicarbonyl having 1 to 4 carbon atoms in the alkoxy part, halogenoalkoxycarbonyl having 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms in the halogenoalkoxy part, alkylamino having 1 to 4 carbon atoms, dialkylamino having 1 to 4 carbon atoms in each alkyl part, haloalkylamino with 1 to 3 halogen atoms and 1 to 4 carbon atoms, alkylaminocarbonyl with 1 to 4 carbon atoms in the alkyl part, dialkylaminocarbonyl with 1 to 4 carbon atoms in each part alkyl, alkylsulphonylate with 1 to 4 carbon atoms, haloalkylsulfonylamino with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms, N, N-bis-alkylsulfonylamino with 1 to 4 carbon atoms in each part alkyl, N, N-bis-halogeno-noalkylsulfonyl-amino with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms in each haloalkyl part, N-alkyl-N-alkylsulfonyl-amino with 1 to 4 carbon atoms in the alkyl part and 1 to 4 carbon atoms in the country Alkylsulphonyl, N-haloalkyl-N-halogenoalkylsulfonyl-amino with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms in the haloalkyl part and with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms in the halogenoalkylsulfonyl part, N-alkylcarbonyl-N-alkylsulfonyl-amino with 1 to 4 carbon atoms in the alkyl part of the alkylcarbonyl group with 1 to 4 carbon atoms in the alkylsulfonyl part, N-haloalkylcarbonyl -N-halogenoalkylsulfonyl-amino with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms in the halogenoalkyl part of the haloalkylcarbonyl group and with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms in the halogenoalkylsulfonyl part or means N-alkylsulfonyl-N-phenylcarbonyl-amino with 1 to 4 carbon atoms in the alkylsulfonyl part, optionally substituted one to three times, in the same or in different ways by fluorine , by chlorine, by bromine, by methyl, by ethyl, by n-propyl, by i-propyl, by n-butyl, by i-butyl, by s-butyl, by t-butyl, by dimethylamino, by diethylamino, by methoxy, by ethoxy, by n-propoxy and / or by -propoxy, denotes hydroxy, mercapto, amino, cyano, nitro, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, alkyl with 1 to 4 carbon atoms, alkoxyalkyl with 1 to 4 carbon atoms in the alkyl and 1 or 2 carbon atoms in the alkoxy part, alkoxy with 1 to 4 carbon atoms, haloalkoxy with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms, alkoxyalkoxy with 1 to 4 carbon atoms carbon in each part alkoxy, alkylthio with 1 to 4 carbon atoms, haloalkylthio with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms, alkylsulfinyl with 1 to 4 carbon atoms, haloalkylsulfinyl with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms, alkylsulfonyl with 1 to 4 carbon atoms, halogenoalkylsulfonyl with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms, alkylcarbonyl with 1 to 4 carbon atoms in the alkyl part, halogenalkylcarbonyl with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms in the haloalkyl part, alkoxycarbonyl with 1 to 4 carbon atoms in the alkoxy part, haloalkoxycarbonyl with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms in the halogenoalkoxy part, alkylamino with 1 to 4 carbon atoms, dialkylamino with 1 to 4 carbon atoms in each alkyl part, haloalkylamino with 1 to 3 halogen atoms and 1 to 4 carbon atoms, alkylaminocarbonyl with 1 to 4 carbon atoms in the alkyl part, dialkylaminocarbonyl with 1 to 4 carbon atoms in each alkyl part, alkylsulfonylamino with 1 to 4 carbon atoms, halogenoalkylsulfonylamino with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms, N, N-bis-alkylsulfonylamino with 1 to 4 carbon atoms in each part alkyl, N, N-bis-halogenoalkylsulfonyl-amino with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms in each haloalkyl part, N-alkyl, N-alkylsulfonyl-amino with 1 to 4 carbon atoms carbon in the alkyl part and the 4 carbon atoms in the part alkylsulfonyl, N-halogeno-N-halogenoalkylsulfonyl-amino with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms in the haloalkyl part and with 1 to 3 fluorine atoms and / or chlorine and 1 to 4 carbon atoms in the halogenoalkylsulfonyl part, N-alkylcarbonyl, N-alkylsulfonyl-amino with 1 to 4 carbon atoms in the alkyl part of the alkylcarbonyl group and 1 to 4 carbon atoms in the alkylsulfonyl part, N-halogenoalkylcarbonyl-N-halogensalkylsulfonyl-amino with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms in the halogenoalkyl part of the haloalkylcarbonyl group and with 1 to 3 fluorine atoms and / or of chlorine and 4 carbon atoms in the halogenoalkylsul-fonyl part or means N-alkylsulfonyl-N-phenylcarbonyl-amino with 1 to 4 carbon atoms in the alkylsulfonyl part optionally substituted one to three times in the same or in the same way different by fluorine, by chlorine, by bromine, by methyl, by ethyl or, by n-propyl, by i-propyl, by n-butyl, by i-butyl, by s-butyl, by t-butyl, by dimethylamino, by diethylamine, by methoxy, by ethoxy, by n-propoxy and / or by i-propoxy, and m means the numbers 0, 1 or 2, with R5 being the same or different residues when m means 2, or Het means the rest of the formula where R 6 signifies hydroxy, mercapto, amino, carboxy, carbamoyl, thiocarbamoyl, alkoxyalkyl with 1 to 4 carbon atoms in the alkyl part and 1 or 2 carbon atoms in the alkoxy part, alkoxy with 1 to 4 carbon atoms, haloalkoxy with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms, alkoxyalkoxy co to 1 to 4 carbon atoms in each part alkoxy, alkylthio with 1 to 4 carbon atoms, halogenoalkylthio with 1 to 3 carbon atoms fluorine and / or chlorine and 1 to 4 carbon atoms, alkylsulfinyl with 1 to 4 carbon atoms, haloalkylsulfinyl with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms, alkylsulfonyl with 1 to 4 atoms of carbon, halogenoalkylsulfonyl with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms, alkylcarbonyl with 1 to 4 carbon atoms in the alkyl part, halogenoalkylcarbonyl with 1 to 3 fluorine atoms and / or of chlorine and 1 to 4 carbon atoms in the haloalkyl part, alkoxycarbonyl with 1 a 4 carbon atoms in the alkoxy part, halogen-alkoxycarbonyl with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms in the halogenoalkoxy part, alkylamino with 1 to 4 carbon atoms, dialkylamino with 1 to 4 carbon atoms in each alkyl part, halogenoalkylated with 1 to 3 halogen atoms and 1 to 4 carbon atoms, alkylaminocarbonyl with 1 to 4 carbon atoms in the alkyl part, dialkylaminocarbonyl with 1 to 4 carbon atoms in each alkyl part, alkylsulfonylamino with 1 to 4 carbon atoms, halogenoalkylsulfonylamino with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms, N, N-bis-alkylsulfonylamino with 1 to 4 carbon atoms in each part alkyl, N, N-bis-halogenoalkylsulfonylamino with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms in each haloalkyl part, N-al-quil-N-alkylsulfonyl-amino with 1 to 4 carbon atoms carbon in the alkyl part and 1 to 4 carbon atoms in the alkylsulfonyl part or, N-haloalkyl-N-halogenoalkyl-sulfonyl-ane with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms in the haloalkyl part and with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms in the haloalkenyl sulphonyl portion, N-alkylcarbonyl-N-alkylsulfonyl amino with 1 to 4 carbon atoms in the alkyl part of the alkylcarbonyl group and 1 to 4 carbon atoms in the alkylsulfonyl part, N -halogenoalkylcarbonyl-N-halogenoalkylsulfonyl-amino with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms in the haloalkyl part of the haloalkylcarbonyl group and with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms in the halogenoalkylsulfonyl part or in the N-alkylsulfonyl-N-phenylcarbonyl amino group with 1 to 4 carbon atoms in the alkylsulfonyl part, optionally substituted one to three times, in the same or different forms by fluorine, by chlorine, by bromine, by methyl, by ethyl, by n-propyl, by -propyl, by n-butyl, by i-butyl, by s-butyl, by t-butyl, by dimethylamino, by diethylamino, by methoxy, by ethoxy, by n-propoxy and / or by i-propoxy, ignites hydroxy, mercapto, amino, cyano, nitro, car-boxi, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, alkyl with 1 to 4 carbon atoms, alkoxyalkyl with 1 to 4 carbon atoms in the alkyl part and 1 or 2 atoms of carbon in the part alkoxy, alkoxy with 1 to 4 carbon atoms, haloalkoxy with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms alkoxyalkoxy with 1 to 4 carbon atoms in each part alkoxy, alkylthio with 1 to 4 carbon atoms, halogen-noalkylthio with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms, alkylsulfinyl with 1 to 4 carbon atoms, haloalkylsulfinyl with 1 to 3 fluorine atoms and / or of chloro and 1 to 4 carbon atoms, alkylsulfonyl with 1 to 4 carbon atoms, halogenalkylsulfonyl with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 atom s of carbon, alkylcarbonyl with 1 to 4 carbon atoms in the alkyl part, haloalkylcarbonyl with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms in the haloalkyl part, alkoxycarbonyl with 1 to 4 carbon atoms in the alkoxy part, halogenoalkoxycarbonyl with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms in the halogenoalkoxy part, alkylamino with 1 to 4 carbon atoms, dialkylamino with 1 to 4 carbon atoms in each alkyl part, haloalkylamino with 1 to 3 halogen atoms and 1 to 4 carbon atoms, alkylaminocarbonyl with 1 to 4 carbon atoms in the alkyl part, dialkylaminocarbonyl with 1 to 4 carbon atoms in each part alkyl, alkylsulfonylamino with 1 to 4 carbon atoms, halogenoalkylsulfonylamino with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms, N, N-bis-alkylsulfonylamino with 1 to 4 ato-mos carbon in each alkyl part, N, N-bis-halogeno-noalkylsulfonyl-amino with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms in each haloalkyl part, N-alkyl-N-alkylsulfonyl-amino with 1 to 4 carbon atoms in the alkyl part and 1 to 4 carbon atoms in n the part alkylsulfonyl, N-halogenoalkyl-N-halogenoalkylsulfonyl-amino with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms in the haloalkyl part and with 1 to 3 fluorine atoms and / or of chlorine and 1 to 4 carbon atoms in the halogenoalkylsulfonyl part, N-alkylcarbonyl-N-alkylsulfonylamino with 1 to 4 carbon atoms in the alkyl part of the alkylcarbonyl group and 1 to 4 carbon atoms in the alkylsulfonyl part, N-haloalkylcarbonyl -N-halogenoalkylsulfonyl-amino with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms in the halogenoalkyl part of the haloalkylcarbonyl group and with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 atoms of carbon in the halogenoalkylsulphonyl part or means N-alkylsulfonyl-N-phenylcarbonyl-amino with 1 to 4 carbon atoms in the alkylsulfonyl part, optionally substituted one to three times, in the same or in different ways by fluorine, chlorine, bromine, methyl, ethyl, by n-propyl, by i-propyl, by n-butyl, by i-butyl, by s-butyl, by t-butyl, by dimethylamino, by diethylamino, by methoxy, by ethoxy, by n-propoxy and / or by i-propoxy, and n means the numbers 0, 1 or 2, where R7 is the same or different when n means 2, or Het means the rest of the formula where R8 signifies hydrogen, fluorine, chlorine, bromine, cyano, alkyl with 1 to 4 carbon atoms, halogenalkyl with 1 to 2 carbon atoms and 1 to 5 fluorine and / or chlorine atoms or means nitro and R9 means amino, alkylamino with 1 to 4 carbon atoms, dialkylamino with 1 to 4 carbon atoms in each alkyl part, haloalkylamino with 1 to 3 halogen atoms and 1 to 4 carbon atoms, alkylaminocarbonyl with 1 to 4 carbon atoms in the alkyl part dialkylaminocarbonyl with 1 to 4 carbon atoms in each alkyl part, alkylsulfonylamino with 1 to 4 carbon atoms, halogenoalkylsulfonylamino with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms N, N-bis-alkylsulfonylamino with 1 to 4 carbon atoms in each alkyl part, N, N-bis-halogenoalkylsulfo-nil-amino with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms in each halide-alkyl part, N- alkyl-N-alkylsulfonyl-amino with 1 to 4 carbon atoms in the al part and 1 to 4 carbon atoms in the part alkylsulfonyl, N-halogenoalkyl-N-halogenolalkylsulfonyl-amino with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms in the haloalkyl part and with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms in the halogenoalkylsul-fonyl part, N-alkylcarbonyl-N-alkylsulfonyl-amino with 1 to 4 carbon atoms in the alkyl part of the alkylcarbonyl group and 1 to 4 carbon atoms in the alkylsulfonyl part, N-halogenoalkylcarbonyl-N-halogeno-alkylsulfonyl-amino with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms in the halogenoalkyl part of the halogenoalkylsulfonyl group and 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms in the halogenoalkylsulfonyl part or means N-alkyl-sulfonyl-N-phenylcarbonyl-amino having 1 to 4 carbon atoms in the alkylsulfonyl part, optionally substituted by one three times, in the same or different ways by fluorine, by chlorine, by bromine, by methyl, by ethyl, by n-propyl, by i-propyl, by n-butyl, by i-butyl, by s-butyl, by t-butyl, by dimethylamino, by diethylamino, by methoxy, by ethoxy, by n-propoxy and / or by i-propoxy. Particular preference is given to heterocyclyluracils of the formula (I), in which R 1 is hydrogen, methyl, ethyl or difluoromethyl, R 2 is carboxy, methoxycarbonyl, cyano, carbamoyl, thiocarbamoyl or means methyl or ethyl substituted one to three times, same or of different forms by fluorine and / or by chlorine, R3 means hydrogen, fluorine, chlorine, bromine or methyl and Het means the rest of the formula where R 4 signifies hydroxy, mercapto, amino, cyano, nitro, carboxy, carbamoyl, thiocarbamoyl, alkoxyalkyl with 1 02 carbon atoms in the alkyl part and 1 or 2 carbon atoms in the alkoxy part, alkoxy with 1 to 4 carbon atoms, halogenalkoxy with 1 to 3 fluorine and / or chlorine atoms and 1 or 2 carbon atoms, alkoxyalkoxy having 1 or 2 carbon atoms in each part alkoxy, alkylthio having 1 to 2 carbon atoms, halogenalkylthio with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms, alkylsulfinyl with 1 to 4 carbon atoms, haloalkylsulfinyl with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms, alkylsulfonyl with 1 to 4 carbon atoms, haloalkylsulfonyl with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms, alkylcarbonyl with 1 to 4 carbon atoms in the alkyl part, halogen alkylcarbonyl with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 atoms carbon in the haloalkyl part, alkoxycarbonyl with 1 to 4 carbon atoms in the alkoxy part, haloalkoxycarbonyl with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms in the halogenoalkoxy part, alkylamino with 1 to 3 carbon atoms, dialkylamino with 1 to 3 carbon atoms in each alkyl part, haloalkylalkono with 1 to 3 fluorine and / or chlorine atoms and 1 to 3 carbon atoms, alkylaminocarbonyl with 1 to 4 carbon atoms in the I rent, dialkylaminocarbonyl with 1 to 4 carbon atoms in each alkyl part, alkylsulfonylamino with 1 to 4 carbon atoms, halogenoalkylsulfonylamino with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms, N, N-bis- alsuylsulfonylamino having 1 to 4 carbon atoms in each alkyl part, N, N-bis-halogenoalkylsulfonyl-amino having 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms in each haloalkyl part, N-alkyl- N-Alkylsulfonyl-amino having 1 to 4 carbon atoms in the alkyl part and 1 to 4 carbon atoms in the alkylsulfonyl part, N-halogenoalkyl-N-halogenoalkylsulfonyl amine with 1 to 3 fluorine atoms and / or chlorine and 1 to 4 carbon atoms in the haloalkyl part and 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms in the halogenoalkylsulfonyl part, N-alkylcarbonyl-N-alkylsulphonyl-amino with 1 to 4 carbon atoms in the alkyl part of the alkylcarbonyl group and 1 to 4 carbon atoms in the alkylsulfoni part it, N-halogenoalkylcarbonyl-N-halogenoalkylsulfonyl-amino with the 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms in the halogenoalkyl part of the haloalkylcarbonyl group with 1 to 3 fluorine atoms and / or chloro and 1 to 4 carbon atoms in the halogenoalkylsulfo-nyl part or means N-alkylsulfonyl-N-phenylcarbonyl amine with 1 to 4 carbon atoms in the alkylsulfonyl part optionally substituted one to three times, equal or in different forms by fluorine, chlorine, bromine, methyl, ethyl, dimethylamino, diethylamino, methoxy and / or ethoxy, hydroxy, mercapto, amino, cyano, nitro, carboxy, carbamoyl , thiocarbamoyl, fluorine, chlorine, bromine, iodine, alkyl with 1 to 4 carbon atoms, alkoxyalkyl with 1 or 2 carbon atoms in the alkyl part or 1 or 2 carbon atoms in the alkoxy part, alkoxy with 1 to 4 atoms carbon, haloalkoxy with 1 to 3 fluorine and / or chlorine atoms and 1 or 2 carbon atoms xalkoxy with 1 or 2 carbon atoms in each part alkoxy, alkylthio with 1 or 2 carbon atoms, halogen-noalkylthio with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms, alkylsulfinyl with 1 to 4 carbon atoms carbon atoms, halogenoalkylsulfinyl with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms, alkylsulfonyl with 1 to 4 carbon atoms, halogenoalkylsulfonyl with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms, alkylcarbonyl with 1 to 4 carbon atoms in the alkyl part, halogenoalkylcarbonyl with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms in the haloalkyl part, alkoxycarbonyl with 1 to 4 carbon atoms in the alkoxy part, halogenoalkoxycarbonyl with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms in the halogenoalkoxy part, alkylamino with 1 to 3 carbon atoms, dialkylamino with 1 to 3 carbon atoms in each part alkyl, haloalkylamino with 1 to 3 fluorine atoms r and / or of chlorine and 1 to 3 carbon atoms, alkylaminocarbonyl with 1 to 4 carbon atoms in the alkyl part, dialkylaminocarbonyl with 1 to 4 carbon atoms in each alkyl part, alkylsulfo-nylamino with 1 to 4 carbon atoms, haloalkylsulfonylamino with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms, N, N-bis-alkylsulfonylamino with 1 to 4 carbon atoms in each alkyl part, N, N-bis-halogenoalkylsulfonyl- amino with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms in each halogenoalkyl part, N-alkyl-N-alkylsulfonylamino with 1 to 4 carbon atoms in the alkyl part and 1 to 4 carbon atoms in the part alkylsulfonyl, N-halogenoalkyl-N-halogenoalkylsulfonyl-amino with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms in the halogenoalkyl part and with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms in the halogenoalkylsulfonyl part, N-alkylcarbonyl-N-alkylsulfonyl-amino with 1 to 4 carbon atoms in the alkyl part of the alkylcarbonyl group and 1 to 4 carbon atoms in the alkylsulfonyl part N-halogenoalkylcarbonyl-N-halogenoalkylsulfonyl-amino with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms carbon in the halogenoalkyl part of the haloalkylcarbonyl group and with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms in the halogenoalkylsulfonyl part or means N-alkylsulfonyl-N-phenylcarbo-nil-amino with 1 to 4 carbon atoms in the alkylsulfonyl part, optionally substituted one to three times, in the same or different ways by fluorine by chlorine, by bromine, by methyl, by ethyl, by dimethylamino, by diethylamino, by methoxy and / or by ethoxy, and means the numbers 0, 1 or 2, where R5 is the same or different when m means 2, or Het means the rest of the formula where R 6 signifies hydroxy, mercapto, amino, carboxy, carbamoyl, thiocarbamoyl, alkoxyalkyl with 1 or 2 carbon atoms in the alkyl part and 1 or 2 carbon atoms in the alkoxy part, alkoxy with 1 to 4 carbon atoms halogenoalkoxy with 1 to 3 fluorine and / or chlorine atoms and 1 or 2 carbon atoms, alkoxyalkoxy with 1 or 2 carbon atoms in each part alkoxy, alkylthio with 1 0 2 carbon atoms, halogenoalkylthio with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms, alkylsulfinyl with 1 to 4 carbon atoms, halogenoalkylsulfinyl with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms, alkylsulfonyl with 1 to 4 carbon atoms, halogenoalkylsulfonyl with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms, alkylcarbonyl with 1 to 4 carbon atoms in the alkyl part, halogenoalkylcarbonyl with 1 to 3 fluorine atoms and / o of chlorine and 1 to 4 carbon atoms in the haloalkyl part, alkoxycarbonyl with 1 to 4 carbon atoms in the alkoxy part, halogen-alkoxycarbonyl with 1 to 3 fluorine and / or chlorine atoms and 4 carbon atoms in the halogenoalkoxy part, alkylamino with 1 to 3 carbon atoms, dialkylamino with 1 to 3 carbon atoms in each alkyl part, ha-linoalkylamino with 1 to 3 fluorine and / or chlorine atoms and 1 to 3 carbon atoms, alkylaminocarbonyl with 1 to 4 carbon atoms in the alkyl part, dialkylaminocarbonyl with 1 to 4 carbon atoms in each alkyl part, alkylsulfonylamino with 1 to 4 carbon atoms, halogenoalkylsulfonylamino with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms, N, N-bis-a l-alkylsulfonylamino having from 1 to 4 carbon atoms in each alkyl part, N, N-bis-halogenoalkylsulfonylamino having 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms in each haloalkyl part, N-alkyl- N-Alkylsulfonyl-amino having 1 to 4 carbon atoms in the alkyl part and 1 to 4 carbon atoms in the alkylsulfonyl part, N-halogenoalkyl-N-halogenoalkylsulfonyl-amino having 1 to 3 fluorine atoms and / or chlorine and 1 to 4 carbon atoms in the halogen-alkyl part and with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms in the halogenoalkylsulfonyl part, N-alkylcarbonyl-N-alkylsulfonyl-amino with 1 to 4 carbon atoms in the alkyl part of the al-quilcarbonyl group and 1 to 4 carbon atoms in the part alkylsulfonyl, N-halogenoalkylcarbonyl-N-halogeno-alkylsulfonyl-amino with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms in the haloalkyl part of the haloalkylcarbonyl group and with 1 to 3 fluorine atoms and / or of chlorine and 1 to 4 carbon atoms in the halogenoalkylsulphonyl part or means N-alkylsulfonyl-N-phenylcarbonyl-amino with 1 to 4 carbon atoms in the alkylsulfonyl part, optionally substituted, from one to three times, of The same or different forms, by fluorine, chlorine, bromine, methyl, ethyl, dimethylamino, diethyl-amino, methoxy and / or ethoxy, are hydroxy, mercapto, amino, cyano, nitro, carboxy , carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, alkyl with 1 to 4 carbon atoms, alkoxyalkyl with 1 or 2 carbon atoms in the alkyl part, and 1 or 2 carbon atoms in the alkoxy part, alkoxy with 1 to 4 carbon atoms, haloalkoxy with 1 to 3 fluorine and / or chlorine atoms and 1 or 2 carbon atoms alkoxyalkoxy with 1 or 2 carbon atoms in the alkoxy part, alkylthio with 1 or 2 carbon atoms, halogen noalkylthio with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms, alkylsulfinyl with 1 to 4 carbon atoms carbon, halogenoalkylsulfinyl with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms, alkylsulfonyl with 1 to 4 carbon atoms, halogenoalkylsulfonyl with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 atoms carbon, alkylcarbonyl with 1 to 4 carbon atoms in the alkyl part, ha-loloalkylcarbonyl with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms in the haloalkyl part, alkoxycarbonyl with 1 to 4 carbon atoms carbon in the alkoxy part, haloalkoxycarbonyl with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms in the halogenoalkoxy part, alkylamino with 1 to 3 carbon atoms, dialkylamino with 1 to 3 carbon atoms in each alkyl part, haloalkyl- amino with 1 to 3 fluorine and / or chlorine atoms and 1 to 3 carbon atoms, alkylaminocarbonyl with 1 to 4 carbon atoms in the alkyl part, dialkylaminocarbonyl with 1 to 4 carbon atoms in each alkyl part , alkylsulfonylamino with 1 to 4 carbon atoms, halogenoalkylsulfonylamino with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms, N, N-bis-alkylsulfonylamino with 1 to 4 carbon atoms in each alkyl part, N, N-bis-halogenoalkylsulfonylamino with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms in each halogenoalkyl part, N-alkyl-N-alkylsulfonyl-amino with 1 to 4 carbon atoms in the part alkyl and 1 to 4 carbon atoms in the alkylsulfonyl part, N-haloalkyl-N-halo-g enoalkylsulfonyl-amino with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms in the haloalkyl part and with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms in the halogenoalkylsulfonyl part , N-alkylcarbonyl-N-alkylsulfonyl-amino with 1 to 4 carbon atoms in the alkyl part of the alkylcarbonyl group and 1 to 4 carbon atoms in the alkylsulfonyl part, N-halogenoalkylcarbonyl-N-halogeno-alkylsulfonyl-amino with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms in the haloalkyl part of the haloalkylcarbonyl group and with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 fluorine and / or chlorine atoms and 1 to 4 carbon atoms in the halogenoalkylsulfonyl part or means N-alkylsulfonyl-N-phenylcarbonyl-amino having 1 to 4 carbon atoms in the alkylsulfonyl part optionally substituted one to three times, in the same or in different ways by fluorine , by chlorine, by bromine, by methyl, by ethyl by dimethylamin or, by diethylol, by methoxy and / or by ethoxy, n means the numbers 0, 1 or 2, with R7 being the same or different residues when n means 2, Het means the rest of the formula where R8 signifies hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec. -butyl, i-butyl, tere. butyl, trifluoromethyl or nitro and R 9 means amino, alkylamino with 1 to 3 carbon atoms, dialkylamino with 1 to 3 carbon atoms in each alkyl part, haloalkylamino with 1 to 3 fluorine and / or chlorine atoms and 1 to 3 carbon atoms, alkylaminocarbonyl with 1 to 4 carbon atoms in the alkyl part, dialkylaminocarbonyl with 1 to 4 carbon atoms in each alkyl part, alkylsulfonylamino with 1 to 4 carbon atoms, halogenoalkylsulfonylamino with 1 to 3 fluorine atoms and / o of chloro and 1 to 4 carbon atoms, N, N-bis-alkylsulfonylamino with 1 to 4 carbon atoms in each alkyl part, N, N-bis-halogenoalkylsulfonyl-a with 1 to 3 fluorine atoms and / or of chlorine and 1 to 4 carbon atoms in each part haloalkyl, N-alkyl-N-alkylsulfonyl-amino with 1 to 4 carbon atoms in the alkyl part and 1 to 4 carbon atoms in the alkylsulfonyl part, N-ha - Linoalkyl-N-halogenoalkylsulfonyl-amino with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms in the haloalkyl part and with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 carbon atoms in the halogenoalkylsulfonyl part, N-alkylcarbonyl-N-alkylsulfonyl-amino with 1 to 4 carbon atoms in the alkyl part of the alkylcarbonyl group and 1 to 4 carbon atoms in the part alkylsulfonyl, N-haloalkylcarbonyl-N-halogenoalkylsulfonyl-amino with 1 to 3 fluorine and / or chlorine atoms and 1 to 4 atoms carbon in the halogenoalkyl part of the haloalkylcarbonyl group and with 1 to 3 fluorine and / or chloro atoms and 1 to 4 carbon atoms in the halogenoalkylsulfonyl part or means N-alkylsulfonyl-N-phenylcarbonyl amino with 1 to 4 carbon atoms in the alkylsulfonyl part, optionally substituted one to three times, in the same or different ways by fluorine, chlorine, bromine, methyl, ethyl, dimethylamino, diethylamino, methoxy and / or ethoxy. Heterocyclyluracils of the formula (I), in which R 1 is hydrogen, methyl, ethyl or difluoromethyl, R 2 means carboxy, methoxycarbonyl, cyano, carbamoyl, thiocarbamoyl, methyl or trifluoromethyl, R 3 is hydrogen and Het are very particularly preferred. means a heterocyclic residues of the following formulas: The definitions of the residues indicated above are valid both for the final products of the formula (I) and also correspondingly for the starting products or for the intermediate products necessary respectively for the preparation. These definitions of the remains can be combined arbitrarily with each other, that is to say even between the indicated intervals. The heterocyclyluracils according to the invention of the formula (I), in which R 1 denotes hydrogen, can be present in the "keto" form of the formula or in the tautomeric form "enol" of the formula In order to simplify, only the "keto" form will always be indicated. If the methyl 3-amino-crotonate and 3-chloro-2-thiocarbamoylpyridin-5-yl-isocyanate are used as starting materials, the development of the process according to the invention (a, variant a) can be represented by means of the scheme of formulas below.
If ethyl 3-amino-4,4,4 trifluorotrothione-to-ethyl and N- (2-chloro-3-cyano-4-methyl-pyridin-6-yl) -ethylcarbamate are used as starting products, it may represent - The development of the process according to the invention (a, variant ß) is to be performed by means of the following formula scheme.
If l- (3-cyano-pyridyl-6-yl) -3,6-dihydro-2,6-dioxo-4-trifluoromethyl-1 (2H) -pyrimidine is used as the starting material and the methyl iodide as component of the reaction, the development of the process according to the invention (b, variant a) can be represented by means of the following formula scheme.
If l- (2-methoxy-pyridin-5-yl) -3,6-dihydro-2,6-dioxo-4-trifluoromethyl-l (2H) -pyrimidine is used as starting material and dimethyl sulfate as the starting material, component of the reaction, the development of the reaction may be represented, the development of the process according to the invention (b, variant β) may be represented by means of the following formula scheme.
The esters of the aminoalkenoic acids required as starting materials in carrying out the process according to the invention (a) are generally defined by means of formula (II). In formula (II), R2 and R3 preferably have or especially those meanings which have already been mentioned above, preferably or particularly preferably R2 and R3 in relation to the description of the compounds of the formula (I) according to the invention. Preferably R means alkyl having 1 to 4 carbon atoms, phenyl or benzyl, more preferably means methyl, ethyl, phenyl or benzyl. Preferably R10 means alkyl having 1 to 3 carbon atoms, especially preferably methyl or ethyl. The esters of the aminoalkenoic acids of the formula (II) are known or can be prepared by processes known per se (see J. Heterocycl Chem. 9 (1972), 513-522). The heterocyclylisocyanates, which are necessary as components of the reaction in carrying out the process according to the invention (a, according to variant a), are generally defined by means of formula (III). In formula (III), Het preferably preferably has those meanings which have already been mentioned above in a preferred manner or in a particularly preferred manner for Het in connection with the description of the compounds of the formula (I) according to invention. The heterocyclylisocyanates of the formula (III) are known or can be prepared by processes known per se (see EP-A 0 555 770 and EP-A 0 600 836). In this way, the heterocyclycylisocyanates of the formula (III) can be prepared if heterocyclylamines of the formula H2N-Het (VII) are reacted, in which Het has the meaning indicated above, with phosgene in the presence of a diluent, such as for example chlorobenzene, at temperatures between -20 ° C and + 150 ° C. The heterocyclylamines of the formula (VII) are known or can be prepared according to methods known in principle. The heterocyclycarbates, which are necessary as components of the reaction in carrying out the process according to the invention (a, according to the variant β), are generally defined by means of formula (IV). In the formula (IV), Het preferably has or especially those meanings which have already been mentioned above in a preferred manner or in a particularly preferred manner for Het in relation to the description of the compounds of the formula (I) according to the invention. Preferably R11 means alkyl having 1 to 4 carbon atoms, phenyl or benzyl, especially methyl, ethyl or phenyl. The heterocyclylcarbamates of the formula (IV) are known or can be prepared by processes known per se (see EP-A 0 555 770 and EP-A 0 600 836). In this way, the heterocycloalkylcarbamates of the formula (IV) can be obtained by reacting heterocyclylamines of the formula H2N-Het (VII), in which Het has the meaning indicated above, with chlorocarbonyl-compounds of the formula RI: LO -CO-C1 (VIII), in which R11 has the meaning indicated above, if appropriate in the presence of an acid acceptor, such as, for example, pyridine and, if appropriate, in the presence of a diluent, such as for example methylene chloride, at temperatures between -20 ° C and + 100 ° C. The heterocyclyluracils, which are necessary as starting materials in carrying out process (b) according to the invention, are generally defined by means of formula (la). In this case, they are products that can be prepared according to the method (a) of the invention. The halogen-compounds necessary as components of the reaction in carrying out the process according to the invention (b, variant a) are defined in general by means of formula (V). In this formula R 12 preferably denotes alkyl having 1 to 3 carbon atoms, optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy. Hal preferably means bromine or iodine. It is particularly preferable to use the halogen compounds of the formula (V), in which R 12 is methyl, ethyl, or difluoromethyl, and Hal is bromine or iodine. The halogen compounds of the formula (V) are known or can be prepared according to processes known in principle. The dialkyl sulfates which are necessary as constituents of the reaction in carrying out the process according to the invention (b, variant β) are generally defined by the formula (VI). In this formula R 13 is preferably alkyl with 1 to 3 carbon atoms, particularly preferably methyl or ethyl. The dialkyl sulfates of the formula (VI) are known. As acid acceptors in carrying out the process according to the invention (a), both customary inorganic and organic bases are suitable according to variant (a) and variant (ß). Preferably, acetates, amides, carbonates, bicarbonates, hydrides, hydroxides or alkanolates of alkali metals or alkaline earth metals can be used, such as sodium, potassium or calcium acetate, lithium amide, sodium, potassium or calcium amide, carbonate. sodium, potassium or calcium, sodium, potassium or calcium bicarbonate, lithium, sodium, potassium or calcium hydride, lithium, sodium, potassium or calcium hydroxide, methanolate, ethanolate, - or i-propanolate, n-, i-, s- or sodium or potassium t-butanolate; in addition also basic organic nitrogenous compounds such as trimethylane, triethylamine, tripropylamine, tributylamine, ethyl-diisopropylamine, N, N-dimethyl-cyclohexylamine, dicyclohexylamine, ethyl-dicyclohexyl ina, N, N-dimethyl-aniline, N, N- dimethyl-benzylamine, pyridine, 2-methyl-, 3-ethyl-, 4-methyl-, 2,4-dimethyl-, 2,6-dimethyl-, 3,4-dimethyl- and 3,5-dimethyl-pyridine, 5-ethyl-2-methyl-pyridine, 4-dimethylamino-pyridine, N-methyl-piperidine, 1,4-diazabicyclo [2,2,2] -octane (DABCO), 1,5-diazabicyclo [4, 3, 0] -on-5-ene (DBN), ol, 8-diazabicyclo [5, 4, 0] -undec-7-ene (DBU). Suitable diluents in the process according to the invention (a) according to the variants () or (ß) are all inert, customary organic solvents and also water. Aliphatic, alicyclic or aromatic hydrocarbons, optionally halogenated, may be used, for example 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 methyl 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 hexa ethylphosphorotriamide; esters such as methyl acetate or ethyl acetate, or sulfoxides, such as dimethylsulfoxide.
The reaction temperatures in the process (a) according to the invention can vary within wide limits. Both in the embodiment of the variant (a) and the variant (ß), the working is generally between 0 ° C and 200 ° C, preferably between 10 ° C and 150 ° C. In carrying out the process (a) according to the invention according to variants (a) and (ß), the reaction is generally carried out under atmospheric pressure. However, it is also possible respectively to work under higher pressure or at lower pressure, for example between 0.1 and 10 bar. When carrying out the process (a) according to the invention, about 1 mole of the aminoalkenoic acid ester of the formula (II), in the case of the variant (a), is used in an approximately equimolar amount of the heterocycloalkylisocyanate of the formula (III) and, in the case of the variant (ß), an approximately equimolar amount of heterocyclic carbamate of the formula (IV). However, it is also possible to use one of the components in a larger excess respectively. The reactions are carried out, in general, in a suitable diluent and in the presence of an acid-accepting agent. In this case, the procedure is carried out in such a way that the reaction mixture is stirred at a necessary temperature for the necessary time and then processed according to usual methods. Coo acid-binding agents are considered in carrying out the process according to the invention (b) according to variants (a) or (ß), all the usual inorganic and organic bases. Preferably, those acid acceptors which have already been mentioned preferably can be used in connection with the description of the process (a) according to the invention. Suitable diluents in carrying out the process according to the invention (b) according to variants (a) or (ß) are all the inert, organic solvents customary for this type of reaction. Preference is given to using nitriles, such as acetonitrile and butyronitrile, in addition ketones, such as acetone, and furthermore amides, such as dimethylformamide and N-methyl-pyrrolidone. The reaction temperatures in carrying out the process according to the invention (b) can vary within wide limits. Work is carried out in the embodiment - in variant (a) in general at temperatures between 0 ° C and 150 ° C, preferably between 10 ° C and 120 ° C, - in the variant (ß) in general at temperatures between 10 ° C and 150 ° C. ° C and 100 ° C, preferably between 15 ° C and 80 ° C. Also in carrying out the process according to the invention (b) according to variants (a) and (ß), generally work is carried out under atmospheric pressure. However, it is also possible to work respectively under higher pressure or, as long as no volatile components are involved in the reaction, under reduced pressure. When carrying out the process according to the invention (b) according to variants (a) and (ß), about 1 mole of the heterocyclyluracil of the formula (la) are generally employed in an approximately equimolar amount of halogen-compound of the formula (V) or dialkyl sulfate of the formula (VI). However, it is also possible to use one of the components in a larger excess respectively. The processing is carried out respectively according to usual methods. 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 compounds according to the invention can be used, for example, in the following plants: Dicotyledonous bad herbs of the kinds; Sinapis, Le-pidium, Galium, Stellaria, Matricaria, Anthemis, Galinso-ga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Ro-tala, Lindernia, La ium, Veronica, Abutilon, Emex, Datu-ra, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ra-nunculus, Taraxacum. Cultures of dicotyledonous classes; Gossypium, Gly-cinema, Beta, Daucus, Phaseolus, Pisum, Solanum, Linu, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis and Cucurbita. Bad monocotyledonous herbs of the kinds; Echino-chloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Oats, Cyperus, Sorghu, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus and Apera. Cultures of monocotyledonous classes; Oryza, Zea, Triticum, Hordeum, Oats, Sécale, Sorghum, Panicum, Sac-charum, Ananas, Asparagus, Allium. The use of the active products according to the invention is not, however, limited in any way to these classes, but extends in the same way also over other plants. 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. Likewise, the compounds can be used to control weeds in permanent crops, for example, in forest installations, ornamental trees, fruit trees, vineyards, citrus trees, walnut trees, bananas, coffee, of the gum tree, oil palms, cocoa, berry and hops, on ornamental and sporting paths and on surfaces for meadows and to selectively control weeds in monocultural crops. annual The compounds of the formula (I) according to the invention are suitable for the control of monocotyledonous and dicotyledonous weeds in monocotyledonous cultures both in the pre-emergence procedure and in the post-emergence process. They also show a good compatibility with the most important crop plants, such as corn and wheat. The active compounds can be converted into customary formulations, such as solutions, solutions, sprayable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension-emulsion concentrates, natural and synthetic materials impregnated with the active product, as well as micro-encapsulated 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, by filling surfactants, that is, emulsifiers and / or dispersants and / or foam generating means. When using water as a filler, it is also possible, for example, to use organic solvents as auxiliary solvents. Suitable liquid di solvents are aromatic hydrocarbons, such as xylene, toluene, or alkyl naphthalenes, chlorinated aromatic hydrocarbons and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example, crude petroleum fractions, alcohols, such as butanol, or glycol, as well as their esters and ethers, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone, or cyclohexane. xanone, strongly polar solvents, 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 earth and ground synthetic minerals, such as highly dispersed silicic acid, aluminum oxide and silicates, as solid excipients for granulates, natural broken and fractionated minerals such as calcite, marble, pumice, sepiolite, dolomite, as well as synthetic granules of inorganic and organic flours, as well as granules of organic materials can be used, such as sawdust, coconut husks, 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, alkyl-sulphonates, alkyl sulfates, aryl sulfonates, as the products of albumin hydrolysis; Suitable dispersants are, for example, lignin sulfite residual liquors and methylcellulose. Adhesives such as carboxymethylcellulose, natural and synthetic polymers, powdered, granulated or in the form of latexes, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, as well as natural phospholipids, such as cephalin and lecithin and phospholipids can be used in the formulations. synthetic Other additives can be mineral and vegetable oils. Dyes, such as inorganic pigments, for 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 salts of iron, manganese, boron, copper, cobalt, molybdenum 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 be used as such or in their formulations also in a mixture with known herbicides for the control of weeds, with possible finished formulations or tank mixtures. In this case, smergism can also occur in some cases. Suitable mixtures are known herbicides, for example: Acetochlor, Acifluorfen (-sodium), Aclonifen, Alachlor, Alloxydim (-sodium), Ametryne, Amidochlor, Amidosulfuron, Asulam, Atrazine, Azimsulfuron, Benazolin, Benfuresate, Bensulfuron (-methyl). ), Bentazon, Benzofenap, Benzoylprop - (- ethyl), Bialaphos, Bifenox, Bro obutide, Bro ofenoxim, Bro oxynil, Butachlor, Butylate, Cafenstrole, Carbetami-de, Chlomethoxyfen, Chloramben, Chloridazon, Chlorimu-ron (-ethyl), Chlornitrofen, Chlorsulfuron, Chlortoluron, Cinmethylin, Cinosulfuron, Clethodim, Clodinafop (propar-gil), Clomazone, Clopyralid, Clopyrasulfuron, Cloransu-lam (-methyl), Cumyluron, Cyanazine, Cycloate, Cyclosulfa-muron, Cycloxydim, Cyhalofop (-butyl) , 2,4-D, 2,4-DB, 2,4-DP, Desmedipham, Diallate, Dicamba, Diclofop (-methyl), Difenzoquat, Diflufenican, Dimefuron, Dimepiperate, Dime-thachlor, Dimethametryn, Dimethenamid, Dinitra ine, Diphenamid, Diquat, Dithiopyr, Diuron, Dymron, EPTC, Esprocarb, Ethalfluralin, Etha metsulfuron (-methyl), Ethofumesate, Ethoxyfen, Etobenzanid, Fenoxaprop-ethyl, Framprop (-isopropyl), Fla prop (-isopropyl-L), Flamprop- (ethyl), Flazasulfuron, Fluazifop (-butyl), Flumetsulam, Flumiclorac (-pentyl), Flu ioxazin, Flumipropyn, Fluo etu-ron, Fluorochloridone, Fluoroglycofen (-ethyl), Flupoxam, Flupropacil, Flurenol, Fluridone, Fluroxypyr, Flurprimi-dol, Flurtamone, Fomesafen, Glufosinate (ammonium), Glyphosate (-isopropylammonium), Halosafen, Haloxyfop (-ethoxyethyl) ) -Hexazinone, I azamethabenz (-methyl), Imazamethapyr, Imaza-mox, Imazapyr, Imazaquin, Imazethapyr, Imazosulfuron, Ioxynil, Isopropalin, Isoproturon, Isoxaben, Isoxafluto-le, Isoxapyrifop, Lactofen, Lenacil, Linuron, MCPA, MCPP, Mefenacet , Metamitron, Metazachlor, Methabenzthiazuron, Metobenzuron, Metobromuron, Metolachlor, Metosulam, Meto-xuron, Metsulfuron (-methyl), Metribuzin, Molinate, Monoli-nuron, Naproanilide, Napropamide, Neburon, Nicosulfuron, Norflurazon, Orbencarb, Oryzalin, Oxadiazon, Oxyfluorfen , Paraquat, Pendimethalin, Phe nmedipham, Piperophos, Preti-lachlor, Primisulfuron (-methyl), Pro etryn, Propachlor, Propanil, Propaquizafop, Propyzamide, Prosulfocarb, Pro-sulfuron, Pyrazolate, Pyrazosulfuron (-ethyl), Pyrazoxyfen, Pyributicarb, Pyridate, Pyrithiobac (-sodium) , Quinchlorac, Quinmerac, Quizalofop (-ethyl), Quizalofop (-p-tefuril), Rimsulfuron, Sethoxydim, Simazine, Simetryn, Sulcotrione, Sulfentrazone, Sulfometuron (-methyl), Sulfosate, Tebutam, Tebuthiuron, Terbuthylazine, Terbutryn, Thenylchlor, Thiafluamide , Thiazopyr, Thidiazimin, Thifensulfuron - (- methyl), Thiobencarb, Thiocarbazil, Tralkoxydim, Trialla-te, Triasulfuron, Tribenuron (-methyl), Triclopyr, Tridip-hane, Trifluralin and Triflusulfuron. It is also possible to mix with other known active ingredients, such as fungicides, insecticides, acaricides, nematicides, bird protection products, nutrient products for the plants and soil structure improving agents. 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 ha. The preparation and use of the active compounds according to the invention are illustrated by means of the following examples.
Examples of obtaining. Example 1.
A mixture consisting of 26.6 g (135 mmol) of ethyl 3-amino-4,4,4-trifluorocrotonate, 24.6 g of potassium carbonate and 200 ml of N-methyl-pyrrolidone is stirred during one hour under nitrogen at 100 ° C. Then 17.5 g (90 mmol) of N- (2-methoxy-pyridin-5-yl) -O-ethyl-carbamate are added and the reaction mixture is heated for 4 hours in the water separator to approximately 130 ° C. Allow to cool to room temperature under nitrogen, then pour into 1 liter of water and extract three times with 100 ml, each time of methylene chloride. After acidification with concentrated hydrochloric acid (up to pH 3), it is left to stand for 1 hour and the crystalline product is isolated by suction filtration. In this way, 18.2 g (71% of the theory of l- (2-methoxy-pyridin-5-yl) -3,6-dihydro-2,6-dioxo-4-trifluoromethyl-1 (2H) are obtained. -pyrimidine with a melting point of 152 ° C.
Obtaining the starting substance of the formula 11 g (0.1 mol) of ethyl chloroformate are added dropwise, under stirring, at room temperature, to a mixture consisting of 12.4 g (0.1 mol) of 2-methoxy-5-amino -pyridine, 15.8 g of pyridine and 100 ml of methylene chloride. The reaction mixture is stirred for 3 hours at room temperature, then washed with IN hydrochloric acid, dried with sodium sulfate and filtered through silica gel. The solvent is carefully removed from the filtrate by distillation under reduced pressure. In this way, 19.7 g of N- (2-methoxy-pyridin-5-yl) -O-ethyl-carbamate are obtained in the form of a crystalline product with a melting point of 76 ° C. Example 2 A mixture of 4.0 g (14 mmol) of 1- (2-methoxy-pyridin-5-yl) -3,6-dihydro-2,6-dioxo-4- is heated to reflux for 18 hours. trifluoromethyl-1 (2H) -pyrimidine, 1.9 g (15 mmol) of dimethyl sulfate, 1.3 g of sodium bicarbonate and 100 ml of acetone. After concentration by evaporation in vacuo of the water tube, the residue is shaken with water / methylene chloride. The organic phase is separated, dried with sodium sulfate and filtered through silica gel. The filtrate is concentrated by evaporation under vacuum of the water pump, the residue is digested with diethyl ether and the precipitated crystalline product is isolated by suction filtration. In this way 3.0 g (54% of theory) of l- (2-methoxy-pyridin-5-yl) -3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl are obtained -l (2H) -pyrimidine with a melting point of 130 ° C. According to the above-mentioned methods, the compounds of the formula (I) indicated in Table 1 below are prepared.
Table l. Table 1 (Continued) Table 1 (Continued) Application examples; Example A. Pre-bud 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 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. Seeds of the test plants are sown in normal soil. After 24 hours the soil is irrigated with the preparation of active product. In this case, the quantity of water per unit area is suitably constant. The concentration of active product in the preparation plays no role, the decisive factor being only the amount of application per unit area. After three weeks, the degree of damage of the plants compared with the development of the untreated control is evaluated in%. They mean: 0% = no effect (same as untreated controls) 100% = total destruction. In this test the compounds according to the preparation examples 7 and 9 are shown, with a partially good compatibility with crop plants, such as corn and soybean, a potent effect against weeds.
Table A Pre-shoot / greenhouse test 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 active product, test plants are sprayed, which have a height of 5-15 cm, so that in each case, the desired quantities of active product are applied per unit of surface. The concentration of the sprayable broths is selected in such a way that the desired quantities of active product are applied in each case in 1000 1 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 the compounds according to the preparation examples 7 and 9 are shown, with a partially good compatibility with crop plants, such as wheat, a potent effect against weeds.
Table B Post-emergence / greenhouse test 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.

Claims (6)

  1. Having described the invention as above, the content of the following claims is claimed as property: 1. - Heterocyclyluracils of the formula characterized because
  2. R1 means hydrogen or means alkyl having 1 to 4 carbon atoms, optionally substituted by cyano, by halogen or by alkoxy with 1 to 4 carbon atoms, R2 means formyl, hydroxyiminomethyl, cyano, carboxy, alkoxycarbonyl, carbamoyl, thiocarbamoyl or alkyl having 1 to 4 carbon atoms, optionally substituted by halogen, R 3 is hydrogen, cyano, halogen or means alkyl having from 1 to 4 carbon atoms, optionally substituted by halogen and Het means the remainder of the formula where R 4 signifies hydroxy, mercapto, amino, nitro, cyano, carbamoyl, thiocarbamoyl, alkoxyalkyl with 1 to 4 carbon atoms in the alkoxy part and the 6 carbon atoms in the alkyl part, alkoxy with 1 to 6 carbon atoms, halogenalkoxy with 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkoxyalkoxy with 1 to 6 carbon atoms in each part alkoxy, alkylthio with 1 to 6 carbon atoms, halogenalkylthio with 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkylsulfinyl with 1 to 6 carbon atoms, halogenoalkylsulfonyl with 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkylsulfonyl with 1 to 6 carbon atoms, halogenoalkylsulfonyl with 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkylcarbonyl with 1 to 6 carbon atoms in the alkyl part, halogen-alkylcarbonyl with 1 to 5 halogen atoms and 1 to 6 carbon atoms in the haloalkyl part, alkoxycarbonyl with 1 to 6 carbon atoms in the part alkoxy, hal Oxygenalkoxycarbonyl with 1 to 5 halogen atoms and 1 to 6 carbon atoms in the halogenoalkoxy, alkylamino with 1 to 6 carbon atoms, dialkylamino with 1 to 6 carbon atoms in each alkyl, haloalkylamino with 1 to 5 carbon atoms halogen and 1 to 6 carbon atoms, alkylaminocarbonyl with 1 to 6 carbon atoms in the alkyl part, dialkylaminocarbonyl with 1 to 6 carbon atoms in each alkyl part, alkylsulfonylamino with 1 to 6 carbon atoms in the alkyl part, haloalkyl sulfonylamino having 1 to 5 halogen atoms and 1 to 6 carbon atoms in the haloalkyl part, N, N-bis-alkyl-sulfonylamino having 1 to 6 carbon atoms in each alkyl part, N, N-bis-halogenoalkylsulfonyl -amino with 1 to 5 halogen atoms and 1 to 6 carbon atoms in each part haloalkyl, N-alkyl-N-alkylsulfonylamino with 1 to 6 carbon atoms in the alkyl part and 1 to 6 carbon atoms in the alkylsulfonyl part , N-haloalkyl-N-hal Oxyalkylsulfonyl-amino with 1 to 5 halogen atoms and 1 to 6 carbon atoms in the haloalkyl part and 1 to 5 halogen atoms and 1 to 6 carbon atoms in the halogenoalkylsulfonyl part, N-alkylcarbonyl-N-alkylsulfonyl-amino with 1 to 6 carbon atoms in the alkyl part of the alkylcarbonyl group and 1 to 6 carbon atoms in the alkylsulfonyl part, N-halogenoalkylcarbonyl-N-halogeno-alkylsulfonyl-amino with 1 to 5 halogen atoms and 1 to 6 carbon atoms in the halogenoalkyl part and 1 to 5 halogen atoms and 1 to 6 carbon atoms in the halogenoalkylsulfonyl part or means N-alkyl-sulfonyl-N-phenylcarbonyl-amino with 1 to 6 carbon atoms in the alkylsulfonyl part, substituted in case given one to three times, in the same or different ways by halogen, by alkyl with 1 to 4 carbon atoms, by dialkylamino with 1 to 4 carbon atoms in each alkyl group and / or by alkoxy with 1 to 4 carbon atoms, also hydroxy , mercapto, amino, nitro, cyano, carboxy, carbamoyl, halogen, alkyl having 1 to 6 carbon atoms, thiocarbamoyl, alkoxyalkyl with 1 to 4 carbon atoms in the alkoxy part and 1 to 6 carbon atoms in the alkyl part, alkoxy with 1 to 6 carbon atoms, haloalkoxy with 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkoxyalkoxy with 1 to 6 carbon atoms in each alkoxy part, alkylthio with 1 to 6 carbon atoms, halogenalkylthio with 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkylsulfinyl with 1 to 6 carbon atoms, haloalkyl sulfinyl with 1 to 6 carbon atoms and 1 to 5 atoms of halogen, alkylsulfonyl with 1 to 6 carbon atoms, halogenoalkylsulfonyl with 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkylcarbonyl with 1 to 6 carbon atoms in the alkyl part, haloxy-noalkylcarbonyl with 1 to 5 carbon atoms halogen and 1 to 6 carbon atoms in the halogenoalkyl part, alkoxycarbonyl with 1 to 6 carbon atoms in the alkoxy part, halogenoalkoxycarbonyl with 1 to 5 halogen atoms and 1 to 6 carbon atoms in the halogenoalkoxy part, alkylamino with 1 to 6 carbon atoms, dialkylamino with 1 to 6 carbon atoms in each alkyl part, halogenoalkylated with 1 to 5 halogen atoms and 1 to 6 carbon atoms, alkylaminocarbonyl with 1 to 6 carbon atoms in the alkyl part, gave alkylaminocarbonyl having 1 to 6 carbon atoms in each alkyl part, alkylsulfonylamino having 1 to 6 carbon atoms in each alkyl part, halogenoalkylsulfonylamino having 1 to 5 halogen atoms and 1 to 6 carbon atoms in the haloalkyl part, N , N-bis-alkyl-sulfonylamino with 1 to 6 carbon atoms in each alkyl part, N, N-bis-halogenoalkylsulfonyl-amino with 1 to 5 halogen atoms and 1 to 6 carbon atoms in each haloalkyl part, N- alkyl-N-alkylsulfonylamino with 1 to 6 carbon atoms in the alkyl part and 1 to 6 carbon atoms in the part alkylsulfonyl N-halogenoalkyl-N-halogenoalkylsulfonyl-amino with 1 to 5 halogen atoms and 1 to 6 carbon atoms in the halogenoalkyl part and 1 to 5 halogen atoms and 1 to 6 carbon atoms in the halogenoalkylsulfo-nyl part, N-alkylcarbonyl-N-alkylsulfonyl-amino with 1 to 6 carbon atoms in the alkyl part of the alkylcarbonyl group and to 6 carbon atoms in the part alquils ulphonyl, N-halogenoalkylcarbonyl-N-halogenalkylsulfonyl-amino with 1 to 5 halogen atoms and 1 to 6 carbon atoms in the haloalkyl part and 1 to 5 halogen atoms and 1 to 6 carbon atoms in the halogenoalkylsulfonyl part or means N-alkylsulphonyl-N-phenylcarbonyl-amino having from 1 to 6 carbon atoms in the alkylsulfonyl part optionally substituted one to three times, in the same or different ways by halogen, by alkyl with 1 to 4 atoms of carbon, by dialkylamino with 1 to 4 carbon atoms in each alkyl group and / or by alkoxy with 1 to 4 carbon atoms, and means integers from 0 to 3, or Het means the rest of the formula where R 6 signifies hydroxy, mercapto, amino, carboxy, carbamoyl, thiocarbamoyl, alkoxyalkyl with 1 to 4 carbon atoms in the alkoxy part and 1 to 6 carbon atoms in the alkyl part, alkoxy with 1 to 6 carbon atoms, haloalkoxy with 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkoxyalkoxy with 1 to 6 carbon atoms in each part alkoxy, alkylthio with 1 to 6 carbon atoms, halogenalkylthio with 1 to 6 carbon atoms and 1 to 5 carbon atoms halogen, alkylsulphinyl with 1 to 6 carbon atoms, halogenoalkylsulfinyl with 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkylsulfonyl with 1 to 6 carbon atoms, haloalkylsulfinyl with 1 to 6 carbon atoms and 5 carbon atoms. halogen, alkylcarbonyl with 12 to 6 carbon atoms in the alkyl part, haloalkylcarbonyl with 1 to 5 halogen atoms and 1 to 3 carbon atoms in the haloalkyl part, alkoxycarbonyl with 1 to 6 carbon atoms in the alkoxy part, halo genoalkoxycarbonyl with 1 to 5 halogen atoms and 1 to 6 carbon atoms in the halogenoalkoxy part, alkylamino with 1 to 6 carbon atoms, dialkylamino with 1 to 6 carbon atoms in each alkyl part, ha-loloalkylamino with 1 to 5 atoms of halogen and 1 to 6 carbon atoms, alkylaminocarbonyl with 1 to 6 carbon atoms in the alkyl part, dialkylamino-carbonyl with 1 to 6 carbon atoms in each alkyl part, alkylsulfonylamino with 1 to 6 carbon atoms in the alkyl part , halogenoalkylsulfonylamino having 1 to 5 halogen atoms and 1 to 6 carbon atoms in the haloalkyl part, N, N-bis-alkylsulfo-nylamino having 1 to 6 carbon atoms in each alkyl part, N, N-bis-halogenoalkylsulfonyl- amino with 1 to 5 halogen atoms and 1 to 6 carbon atoms in each part haloalkyl, N-alkyl-N-alkylsulfonyl-amino with 1 to 6 carbon atoms in the alkyl part and 1 to 6 carbon atoms in the part alkylsulfonyl, N-ha-loloalkyl-N-hal O-Alkylaminosulfonyl-amino with 1 to 5 halogen atoms and 1 to 6 carbon atoms in the haloalkyl part and 1 to 5 halogen atoms and 1 to 6 carbon atoms in the halogenoalkylsulfonyl part, N-alkylcarbonyl-N-alkylsulfonyl-amino with 1 to 6 carbon atoms in the alkyl part of the alkylcarbonyl group and 1 to 6 carbon atoms in the alkylsulfonyl part, N-halogenoalkylcarbonyl-N-halogeno-alkylsulfonyl-amino with 1 to 5 halogen atoms and 1 to 6 carbon atoms in the halogenoalkyl part and 1 to 5 halogen atoms and 1 to 6 carbon atoms in the halogenoalkylsulfonyl part or means N-alkylsul-fonyl-N-phenylcarbonylamino with 1 to 6 carbon atoms in the alkylsulfonyl part, substituted from one to three times in the same or different manner by halogen, by alkyl with 1 to 4 carbon atoms, by dialkylamino with 1 to 4 carbon atoms in each alkyl group and / or by alkoxy with 1 to 4 carbon atoms, ignites hydroxy, mercapto, amino , cyano, nitro, carboxy, carbamoyl, thiocarbamoyl, halogen, alkyl with 1 to 6 carbon atoms, alkoxyalkyl with 1 to 4 carbon atoms in the alkoxy part and 1 to 6 carbon atoms in the alkyl part, alkoxy with 1 to 6 carbon atoms, haloalkoxy with 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkoxyalkoxy with 1 to 6 carbon atoms in each part alkoxy, alkylthio with 1 to 6 carbon atoms, haloalkylthio with 1 to 6 carbon atoms carbon and 1 to 5 halogen atoms, alkylsulfinyl with 1 to 6 carbon atoms, halogenoalkyl-sulfinyl with 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkylsulfonyl with 1 to 6 carbon atoms, halogenoalkylsulfonyl with 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkylcarbonyl with 1 to 6 carbon atoms in the alkyl part, halogenoalkylsulfonyl with 1 to 5 halogen atoms and 1 to 6 carbon atoms in the haloalkyl part, alkoxycarbonyl with 1 to 6 atoms carbon in the part e al-coxy, haloalkoxycarbonyl with 1 to 5 halogen atoms and 1 to 6 carbon atoms in the halogenoalkoxy part, alkylamino with 1 to 6 carbon atoms, dialkylamino with 1 to 6 carbon atoms in each alkyl part, haloalkylamino with 1 to 5 halogen atoms and 1 to 6 carbon atoms, alkylaminocarbonyl with 1 to 6 carbon atoms in the alkyl part, di-alkylalkylcarbonyl having 1 to 6 carbon atoms in each alkyl part, alkylsulfonylamino having 1 to 6 carbon atoms in the alkyl part, halogenoalkylsulphonylamino having 1 to 5 halogen atoms and 1 to 6 carbon atoms in the halogenoalkyl part, N, N-bis-al-quylsulfonylamino having 1 to 6 carbon atoms in each alkyl part, N, N-bis-halogenoalkylsulfonyl-amino having 1 to 5 halogen atoms and 1 to 6 carbon atoms in each haloalkyl part, N-alkyl-N-alkylsulfo-nil-amino with 1 to 6 carbon atoms in the alkyl part and 1 to 6 carbon atoms in the alkylsulfonyl part, N-haloalkyl-N-halogenoalkylsulfonylamino with 1 to 5 atoms of halogen and 1 to 6 carbon atoms in the halide part oalkyl and 1 to 5 halogen atoms and 1 to 6 carbon atoms in the halogenoalkylsulfonyl part, N-alkylcarbonyl-N-alkylsulfonylamino having 1 to 6 carbon atoms in the alkyl part of the alkylcarbonyl group and 1 to 6 carbon atoms in the part alkylsulfonyl, N-halogenoalkylcarbonyl-N-halogenoalkylsulfonyl-a with 1 to 5 halogen atoms and 1 to 6 carbon atoms in the haloalkyl part and 1 to 5 halogen atoms and 1 to 6 carbon atoms in the halogenoalkylsulfonyl part or means N-alkylsulfonyl-N-phenylcarbonyl-amino with 1 to 6 carbon atoms in the alkylsulfonyl part, optionally substituted one to three times, likewise 0 in different ways by halogen, by alkyl with 1 to 4 carbon atoms, by dialkylamino with 1 to 4 carbon atoms in each alkyl group and / or by alkoxy with 1 to 4 carbon atoms, and n means integers from 0 to 3, or Het means the rest of the formula where R8 signifies hydrogen, halogen, cyano, alkyl having 1 to 6 carbon atoms, halogenalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms or means nitro and R9 means amino, alkylamino having 1 to 6 carbon atoms; bond, dialkylamino with 1 to 6 carbon atoms in each alkyl part, haloalkylamino with 1 to 5 halogen atoms and 1 to 6 carbon atoms, alkylaminocarbonyl with 1 to 6 carbon atoms in the alkyl part, dialkylalkonocarbonyl with 1 to 6 carbon atoms in each alkyl part, alkylsulfonylamino with 1 to 6 carbon atoms in the alkyl part, halogenoalkylsulfonylamino with 1 to 5 halogen atoms and 1 to 6 carbon atoms in the haloalkyl part, N, N-bis-alkylsulfonylamino with 1 to 6 carbon atoms in each alkyl part, N, N-bis-halogenoalkylsulfonyl-amino with 5 halogen atoms and 1 to 6 carbon atoms in each haloalkyl part, N-alkyl-N-alkylsulfonyl-amino with 1 to 6 carbon atoms in the alkyl part and 1 to 6 carbon atoms in the alkylsulfonyl part, N-haloalkyl-N-haloalkylsulphonyl-amino with 1 to 5 halogen atoms and 1 to 6 carbon atoms in the haloalkyl part and 1 to 5 atoms of halogen and 1 to 6 carbon atoms in the halogenoalkylsulfonyl part, N-alkylcarbonyl-N-alkylsulfonyl-ao with 1 to 6 carbon atoms in the alkyl part of the alkylcarbonyl group and 1 to 6 carbon atoms in the part alkylsulfonyl, N-halogenoalkylcarbonyl-N-halogenoalkylsulfonyl-amino with 1 to 5 halogen atoms and 1 to 6 carbon atoms in the haloalkyl part and 1 to 5 halogen atoms and 1 to 6 carbon atoms in the halogenoalkylsulfonyl part or means N-alkylsulfonyl-N-phenylcarbonyl amine with 1 to 6 carbon atoms in the alkylsulfonyl part, optionally substituted one to three times, in the same or different ways by halogen, by alkyl with 1 to 4 carbon atoms, by dialkylamino with 1 to 4 carbon atoms in each alkyl group and / or alkoxy with 1 to 4 carbon atoms. 2. Process for obtaining hetero-cyclisuracils of the formula (I) according to claim 1, characterized in that a) aminoalkenoic acid esters of the formula are reacted wherein R 2 and R 3 have the meanings indicated above, R 10 signifies hydrogen or alkyl having 1 to 4 carbon atoms and R means alkyl, aryl or arylalkyl, or a) with heterocyclylisocyanate of the formula 0 = C = N-Het (III ) in which Het has the meaning indicated above, or ß) with heterocyclic carbamates of the formula HO wherein Het has the meaning indicated above and R 11 signifies alkyl, aryl, or arylalkyl, respectively, if appropriate in the presence of an acid-accepting agent and, if appropriate, in the presence of a diluent, or b) heterocyclyluracils are reacted the formula wherein R2, R3 and Het have the meanings given above, either a) with halogen-compounds of the formula R12-Hal (V) wherein R12 means alkyl having 1 to 4 carbon atoms, optionally substituted by cyano, by halogen or by alkoxy with 1 to 4 carbon atoms and Hal means chlorine, bromine or iodine, or ß) with dialkyl sulfates of the formula wherein R 13 means alkyl having 1 to 4 carbon atoms, respectively, optionally in the presence of an acid-accepting agent and, if appropriate, in the presence of a diluent. 3. Herbicidal agents, characterized in that they have a content in at least one heterocyclyluracil of the formula (I) according to claim 1.
  3. 4. Use of the heterocyclyluracils of the formula (I) according to claim 1 for the fight against the bad herbs.
  4. 5. - Procedure for the fight against weeds, characterized in that heterocyclyluracils of the formula (I) are applied, according to claim 1, on weeds and / or on their environment.
  5. 6. Process for obtaining herbicidal agents, characterized in that heterocyclyluracils of the formula (I) are mixed according to claim 1, with extenders and / or with surfactants.
MXPA/A/1999/005618A 1996-12-17 1999-06-16 Heterocyclyluracil MXPA99005618A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19652429.6 1996-12-17

Publications (1)

Publication Number Publication Date
MXPA99005618A true MXPA99005618A (en) 2000-01-01

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