MXPA97006776A - - Google Patents

Description

3-Ariluracils and intermediate products for obtaining them Description The present invention relates to novel 3-aryluracils of the general formula I in which the variables have the following meanings: A hydrogen, methyl or amino; R1 hydrogen or halogen; R 2 is hydrogen, halogen, Ci-Cß-alkyl, Ci-Cβ-halogenoalkyl, Ci-Ce-alkytithium, Ci-Cg-alkylsulfenyl or Ci-Cß-alkylsulfonyl; R3 hydrogen, halogen or Ci-Cβ-alkyl; X oxygen or -N (R7) -, meaning R7 hydrogen, Ci-Cβ-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, (Ci-C-alkyl) carbonyl or Cx-Ce-alkoxy-Ci -Cß-alkyl; Y1, Y2 each independently of the other, oxygen or sulfur; Z oxygen or -N (R8) -; R5, R6, R7, R8 each independently of the other, hydrogen, C? -C6-alkyl, C-C? Alkenyl, C3-C6-alkynyl or C? Ce-alkoxy-Ci-Cg-alkyl or R6 together with R8 represents a second chemical bond; R4 hydrogen, Ci-Cβ-alkyl, C3-C8-cycloalkyl, Ci-Cß-halogenoalkyl, C3-C6-alkenyl, C3-C6-alkynyl, (Ci-Cß-alkyl) carbonyl, (C3-C6) -alkenyl) carbonyl, (C3-C6-alkynyl) carbonyl or C? -C6-alkylsulfonyl, each of the last 9 radicals mentioned can carry, if desired, one to three substituents selected from the following group includes: halogen, nitro, cyano, hydroxy, C3-Cβ-cycloalkyl, Ci-Cd-alkoxy, C3-Ca-cycloalkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C6-C6-alkoxy-C6- alkoxy, Ci-Ce-alkylthio, C? -C6-alkylsulfenyl, Ci-C? -alkylsulfonyl, C? -C6-alkylidenaminooxy, the phenyl, phenoxy or phenylsulfonyl group, which may be unsubstituted or carry from one to three of the following radicals selected from the group comprising: halogen, nitro, cyano, Ci-Ce-alkyl, Ci-Ce-alkoxy and C? C6-haloalkyl, a? -iteryl cyclyl group, hetefc-dicyloxy, heterocycylcarbonyl or 3- to 7-membered heterocyclylcarbonyloxy and containing one to three heteroatoms as ring members, selected from a group comprises two oxygen atoms, two sulfur atoms and 3 nitrogen atoms, the heterocycle of which may be saturated, partially or totally unsaturated or aromatic and carry, if desired, one to three solids selected from the group comprising halogen, nitro, cyano, Ci-Cd-alkyl, Ci-Cd-alkoxy, C] -C6-haloalkyl and (Ci-C-alkyl) carbonyl, a group -CO-R9, -O-CQ-R9, -CO-OR9, -0-CO-OR9, 15 -CO-SR9, -O-CO-SR9, -CO-N (R9) R10, -0 -CO-N (R9) R10, i -N (R9) R10 or -C (NR) -OR12, meaning R9 hydrogen, Ci-Cβ-alkyl, C3-Cß-cycloalkyl, C3-C6-alkenyl, C3-C¡; -alkynyl, Ci-Cg-alkoxy-Ci-Cß-alkyl, (C?-C6-alkoxy) carbonyl-C? -C6-alkyl, phenyl or phenyl-Ci-C? alkyl, which phenyl radicals can be unsubstituted or carry from one to three radicals selected in each case from the group comprising halogen, nitro, cyano, Ci-Cß-alkyl, Ci-Ce-alkoxy and Ci-Ce-haloalkyl, R10 hydrogen, hydroxy, Ci-Cβ-alkyl, C3-Cβ-cycloalkyl, C? -C6-alkoxy, C3-Cs-alkenyloxy or (Ci-C6-alkoxy) carbonyl-Ci-Cd-alkoxy, R11 C ^ Ce-alkoxy, Cs-Cg-alkylene glycol or (C6-alkoxy) carbonyl -Ci-C-alkoxy R12 Ci-Cβ-alkyl, C3-C6-alkenyl or (Ci-Cβ-alkoxy) carbonyl-C? -C6-alkyl; as well as their useful salts in the agriculture of those compounds I, in which A means hydrogen.

The invention also relates to the use of the compounds I as herbicides and / or for desiccation or defoliation of plants, to herbicidal products and products for desiccation and / or defoliation of plants and containing the compounds I as active substances, to processes for combating the growth of unwanted plants and for desiccation and / or defoliation of plants with the compounds I, - to processes for obtaining the compounds I and of herbicidal products and products for the desiccation and / or defoliation of plants using the compounds I, as well as to new intermediate products of formulas IV, V, VIII, X and XII, from which compounds I can be prepared.

EP-A 420 194 already described compounds of the formulas lía and Illa lía nía where Ra is C? -C7-alkyl, C3-C-alkenyl, C3-C-alkynyl, halogen-C] -C6-alkyl, halogen-C3-C6-alkenyl or C? -C-alkoxy-C? -C3-alkyl. Compounds Ha with A = methyl or amino and Illa compounds are attributed to herbal properties.

It is known from WO 90/15057 that, for example, the compounds of the formula Hb where R b means, among other radicals, hydrogen or C 4 -C-alkyl; Rc means hydrogen or certain radicals linked via carbon; Rd and Re mean each time hydrogen, halogen, C, -C 4 -alkyl or phenyl and R 3 'hydrogen, halogen or C, -C 4 -alkyl they also have herbicidal action.

Derivatives of 3- (3-oxo-2H-l, 4-benzoxacin-6-yl) -6-halogenoalkyl-2,4- (lH, 3H) -pyrimidinedione of this type are also known from EP -A 408 382. In this patent they are described as herbicides together with the compounds of the formulas IHb and I where Rf means, for example, hydrogen or C? -C3-alkyl and R9 is hydrogen or certain organic radicals attached via carbon.

According to the teaching a * e the U.S. 5,310,723 also have the 3- (l-alkoxy-lower-chinolin-2-on-7-yl) -l-methyl-6-trifluoromethyluracils herbicidal action.

Finally, the subject of EP-A 477 677 are derivatives of 6- (4,5,6,7-tetrahydro-2H-isoindol-1,3-dion-2-yl), 6- (dimethyl-maleinimide) and 6- (4, 5, 6,7-tetrahydroisoindol-2-yl) -1,4-benzo-xazin-3 (4H) -one which in the nitrogen of the axazine ring carry a group C? -5-alkoxy, C3 -4-alkenyloxy, C3-4-alkynyloxy, cyclopropylmethoxy, C2-3-cyanoalkoxy, Cj.-2-alkoxy-C? -2-alkoxy or C? -2_alkylthio-C? -2-alkoxy. This compound is also attributed herbicidal properties.

However, the herbicidal properties of the known compounds are not always completely satisfactory. Therefore, the present invention was intended to provide new compounds especially herbicidal action that would allow better and more specifically combat unwanted plants.

The object also includes providing new compounds with desiccant / defoliant action.

Therefore, the 3-aryluracils of the formula I were found, as well as their herbicidal action.

In addition, herbicidal products containing the compounds I and having a very good herbicidal action were found. In addition, there were found procedures for obtaining these products and a method for combating the growth of unwanted plants with the compounds I.

H.H In addition, it has been found that cú fsüésßoß I are also suitable for the drying of crop plants, such as cotton, potatoes, rapeseed, sunflowers, soybeans and beans, especially for cotton. Thus, products for desiccation and / or defoliation of plants, processes for obtaining these products and a process for desiccation and / or defoliation of plants with compounds I were found.

The compounds of the formula I may contain, depending on the replacement scheme, one or more centers of chirality, in which case they are present as enantiomeric or diastereomeric mixtures. The object of the invention are both the pure enantiomers or diastereomers as well as their mixtures.

Whenever A means hydrogen, the 3-aryluracils I may be present in the form of their salts useful in agriculture, in which case the type of salt is not critical. Generally, salts of those bases, in which the herbicidal action is not adversely affected, are appropriate in comparison with the free compound I.

Useful salts in agriculture are, above all, the salts of the alkali metals, especially the sodium and potassium salts, of the alkaline earth metals, preferably the calcium and magnesium salts, of the transient metals, and preferably the zinc salts and salts thereof. of iron, as well as ammonium salts, in which the ammonium ion can, if desired, carry one to three substituents C? -C4-alkyl, hydroxy-C? -C4-alkyl and / or a phenyl substituent or benzyl, preferably the salts of diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium and trimethyl- (2-hydroxyethyl) ammonium, in addition the salts of phosphonium, sulfonium, as well as preferably salt <1. There are also rri- (*. £.,., - t, alkyl) sulfonium and sulfoxioni, such as especially the salts of tri- (C? -C4-al-quil) sulfoxonium.

The moieties mentioned for the substituents R 2 to R 10 or as radicals on phenyl rings or heterocycles are collective terms for the detailed enumeration of the individual members of the groups. All carbon chains, namely, all the alkyl, haloalkyl, alkoxy, alkylthio, alkylsulfenyl, alkylsulfonyl, alkylcarbonyl, alkoxycarbonyl, alkenyl, alkenyloxy, alkenylcarbonyl, alkynyl, alkynyloxy, alkynylcarbonyl and alkylaminaminoxy moieties can be linear or branched As indicated otherwise, the halogenated substituents preferably have one to five identical or different halogen atoms. Halogen in each case means fluorine, chlorine, bromine or iodine.

They also mean, for example: Ci-Cβ-alkyl and the alkyl portions of Ci-Cβ-alkoxy-C6-C6-alkyl and (C6-C6-alkoxy) carbonyl-C6-C6-alkyl: methyl, ethyl, n-propyl, -methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methyl butyl, 3-methylbutyl, 2,2-dimethylpropyl, 1- ethylpropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethyl- Tylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3, 3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1, 1, 2-trimethyl-5-propyl, 1,2,2 -trlrt? ethylpropyl, 1-ethyl-l-methylpropyl or l-ethyl-2-methylpropyl; Ci-Cβ-halogenoalkyl: a C? -C6-alkyl radical such as those mentioned above, which are partially or completely substituted by fluoro, chloro, bromo and / or iodo, ie, eg chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl , difluoromethyl, trifluoromethyl, chlorofluoromethyl, diclo-rofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2 -fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3 -difluoro-propyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, 2,2,3 , 3, 3-pentafluoropropyl, heptafluoropropyl, 1- (fluoromethyl) -2-fluoroethyl, 1- (clo-romethyl) -2-chloro-yl, 1- (bromomethyl) -2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl, Nonafluoro-butyl, 5-fluoropen yl, 5-chloropentyl, 5 -bromopen ilo, 5-iodopentyl, undecafluoropentyl, 6-fluorohexyl, 6-chlorohexyl, 6-bromohexyl, 6-iodohexyl or dodecafluorohexyl; phenyl-Ci-Cd-alkyl: eg benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylprop-1-yl, 2-phenylprop-1-yl, 3-phenyl-prop-1-yl, 1-Phenylbut-1-yl, 2-phenylbut-1-yl, 3-phenyl-but-1-yl, 4-phenylbut-1-yl, 1-phenylbut-2-yl, 2-phenyl-but-2- ilo, 3-phenylbut-2-yl, 3-phenylbut-2-yl, 4-phenyl-but-2-yl, l- (phenylmethyl) -et-l-yl, 1- (phenylmethyl) -l- ( -ethyl) -et-l-yl or l-t-phenylmethyl) -pro-l-yl, preferably benzyl, 2-phenylethyl or 2-phenyl-hex-6-yl; C3-C6-alkenyl, as well as the alkenyl portions of C3-C6-alkenyloxy and (C3-C6-alkenyl) carbonyl: prop-1-en-l-yl, prop-2-en-l-yl. 1-Methylethenyl, n-bu-ten-1-yl, n-buten-2-yl, n-buten-3-yl, 1-methyl-prop-1-en-l-yl, 2-methyl-propyl l-en-l-yl, 1-methyl-prop-2-en-l-yl or 2-methyl-prop-2-en-l-yl, n-penten-1-yl, n-penten-2- ilo, n-penten-3-yl, n-penten-4-yl, 1-methyl-but-1-en-l-yl, 2-methyl-but-l-en-l-yl, 3-methyl- but-1-en-l-yl, l-methyl-but-2-en-l-yl, 2-methyl-but-2-en-l-yl, 3-methyl-but-2-en-l- ilo, 1-methyl-but-3-en-l-yl, 2-methyl-but-3-en-l-yl, 3-methyl-; but-3-en-l-yl, 1, l-dimethyl-prop-2-en-l-yl, 1,2-dimethyl-prop-1-en-l-yl, 1,2-dimethyl-propyl 2-en-l-yl, 1-ethyl-prop-l-en-2-yl, l-ethyl-prop-2-en-l-yl, n-hex-1-en-l-yl, n- hex-2-en-l-yl, n-hex-3-en-l-yl, n-hex-4-en-l-yl, n-hex-5-en-l-yl, 1-methyl- pent-l-en-l-yl, 2-methyl-pent-1-en-l-yl, 3-methyl-pent-l-en-l-yl, 4-methyl-pent-1-en-l- ilo, l-methyl-pent-2-en-l-yl, 2-methyl-pent-2-en-l-yl, 3-methyl-pent-2-en-l-yl, 4-methyl-pent-2-en-l-yl, l-methyl-pent-3-en-l-yl, 2-methyl-pent-3-en-l-yl, 3-methyl-pent-3 -in-l-yl, 4-methyl-pent-3-en-l-yl, l-methyl-pent-4-en-l-yl, 2-methyl-pent-4-en-l-yl, 3 -methyl-pent-4-en-l-yl, 4-methyl-pent-4-en-l-yl, 1, l-dimethyl-but-2-en-l-yl, 1,1-dimethyl-put -3-en-l-yl, 1,2-dimethyl-but-l-en-l-yl, 1,2-dimethyl-put-2-en-l-yl, l, 2-dimethyl-but-3 -in-l-yl, 1,3-dimethyl-put-1-en-l-yl, l, 3-dimethyl-but-2-en-l-yl, 1,3-dimethyl-put-3-en -l-ilo, 2,2-dimethyl-but-3-en-l-yl, 2,3-dimethyl-put-1-en-l-yl, 2,3-dimethyl-but-2-en-l -yl, 2,3-dimethyl-put-3-en-l-io, 3, 3-dimethyl-1-but-1-en-1-yl, 3,3-dimethyl-put-2-en-1-yl , 1-ethyl-but-l-en-l-yl, 1-eti-but-2-en-l-yl, l-ethyl-but-3-en-l-yl, 2-ethyl-but-1 -in-l-yl, 2-ethyl-but-2-en-l-yl, 2-ethyl-but-3-en-l-yl, 1, l, 2-trimethyl-prop-2-en-l -yl, l-ethyl-l-methyl-prop-2-en-l-yl, l-ethyl-2-methyl-prop-l-en-l-yl or l-ethyl-2-methyl-prop-2 -in-l-ilo; C3-C6-alkynyl, as well as the alkynyl portions of C3-C6-alkynyloxy and (C3-C6-alkynyl) carbonyl: prop-1-yn-l-yl, prop-2-yn-l-yl, but- 1-in-l-yl, but-l-in-3-yl, but-l-in-4-yl, but-2-yn-l-yl, pent-1-in-l-yl, n- pent-l-in-3-yl, n-pent-l-in-4-yl-n-pent-l-in-5-yl, n-pent-2-yn-l-yl, n-pent-2 -in-4-yl, n-pent-2-yn-5-yl, 3-methyl-but-l-yn-3-yl, 3-methyl-but-l-yn-4-yl, n-hex -1-in-l-yl, n-hex-l-in-3-yl, n-hex-l-in-4-yl, n-hex-l-in-5-yl, n-hex-l -in-6-yl, n-hex-2-yn-l-yl, n-hex-2-yn-4-yl, n-hex-2-yn-5-yl, n-hex-2-yl -6-yl, n-hex-3-yn-l-yl, n-hex-3-yn-2-yl, 3-methyl-pent-1-yn-l-yl, 3-methyl-pent -l-in-3-yl, 3-methyl-pent-l-in-4-yl, 3-methyl-pent-l-in-5-yl, 4-methyl-pent-1-yn-l-yl , 4-methyl-pent-2-yn-4-yl or 4-methyl-pent-2-yn-5-yl; Ci-Cβ-alkoxy, as well as the C de-C6-alkoxy-C?-C6-alkyl alkoxy portions, (Ci-Cg-alkoxy) carbonyl-Ci-Cd-alkyl and (C? -C6-alkoxy) carbonyl-C? -C6-alkoxy: methoxy, ethoxy, n-propoxy, 1-methylethoxy, n-butoxy, 1-methyl-propoxy, 2-methylpropoxy, 1, 1-dimethylethoxy, n -pentoxi, 1-Methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethyl-propoxy, 1, 2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethyl-propoxy, n-hexoxy, 1-methylpentoxy, 2-methylpepthoxy , 3-me-tilpentoxy, 4-meti-pentoxy, 1,1-dimethylbutoxy, 1,2-dimethyl-tabutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethyl-tabutoxy, 3, 3-dimethylbuto ?, 1-ethylbutoxy, 2-ethylbutoxy, 1, 1,2-trimethylpropoxy, 1,2,2-trimethyl-propoxy, 1-ethyl-1-methylpropoxy or 1-ethyl-2-methylpropoxy; Ci-Cd-alkylthio: methylthio, ethylthio, n-propylthio, 1-methylethylthio, n-butylthio, 1-methylpropylthio, 2-methylpropylthio, 1,1-dimethylethylthio, n -pentylthio, 1-methylbutylthio, 2-methyl- butylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethyl-propylthio, n-hexylthio, 1,1-dimethylpropylthio, 1,2-dimethyl-propylthio, 1-methyl-pentthylthio, 2-methylpentylthio, 3-methyl- pentthylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1,2-di-methylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2- ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2-trimethyl-propylthio, 1-ethyl-l-methylpropylthio or l-ethyl-2-methylpropylthio; (Ci-Cß-alkyl) carbonyl: me -carbonyl, ethylcarbonyl, n-propylcarbonyl, 1-methylethylcarbonyl, n-butylcarbonyl, 1-me-1-propylcarbonyl, 2-methylpropylcarbonyl, 1,1-dimethylethylcarbonyl, n-pentylcarbonyl, 1- methylbutylcarbo-nyl, 2-me-ilbu-1-carbonyl, 3-methylbutylcarbonyl, 1,1-dimethylpropylcarbonyl, 1,2-dimethylpropylcarbonyl, 2,2-dimethylpropylcarbonyl, 1-ethylpropylcarbonyl, hexylcarbonyl, 1-methylpentylcarbonyl, 2-methylpentylcarbonyl, 3- methylpentylcarbonyl, 4-methylpentylcarbonyl, 1,1-dimethylbutylcarbonyl, 1,2-dimethylbuylcarbonyl, 1,3-dimethylbutylcarbonyl, 2,2-dimelimbutoylcarbonyl, 2,3-dimethylbutylcarbonyl, 3,3-dimethylbutylcarbonyl , 1-ethylbutylcarbo-nyl, 2-ethylbutylcarbonyl, 1, 1,2-trimethylpropylcarbonyl, 1,2,2-trimethylpropylcarbonyl, 1-ethyl-1-methylpropylcarbo-nyl or 1-ethyl-2-methylpropylcarbonyl; C 1 -C 4 -alkylsulfenyl: methylsulfenyl, ethylsulphenyl, n-propylsulphenyl, 1-methylethylsulphenyl, n-butylsulphenyl, 1-methylpropylsulphenyl, 2-methylpropylsulfenyl, 1,1-dimethylethyl-sulphenyl, n-pentylsulphenyl, 1-methylbutylsulfe-nile, methylbutylsulfenyl, 3-methylbutylsulfenyl, 2,2-dimethylpropylsulfenyl, 1-ethylpropylsulfenyl, 1,1-di-methylpropylsulfenyl, 1,2-dimethylpropylsulfenyl, n-hexyl sulfenyl, 1-methylpentylsulfenyl, 2-methylpentylsulfenyl, 3-methylpentylsulfenyl, -me ilpentylsulfenyl, 1,1-dimethylbutylsulfenyl, 1,2-dimethylbutylsulfenyl, 1,3-dimethyl-butylsulfenyl, 2,2-dimethylbutylsulfenyl, 2,3-dimethylbuylsulfenyl, 3,3-dimethylbutylsulfenyl, 1-ethylbutylsulphenyl- nyl, 2-ethylbutylsulfenyl, 1, 1,2-trimethylpropyl sulfenyl, 1, 2,2-trimethylpropylsulfenyl, 1-ethyl-1-methylpropylsulfe-nyl or 1-ethyl-2-methylpropylsulfenyl; C? -C4-alkylsulfonyl: methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, 1-methylethylsulfonyl, n-butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl, 1,1-dimethylethyl-sulfonyl, n-pentylsulfonyl, 1-methylsbutyl-sulphonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, 1,1-di-methylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, n-hexyl-sulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3- methylpentylsulfonyl, 4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl, 1- ethylbutylsulfo-f *. nyl, 2-ethyl-1-ethyl-1-phonyl, 1-yl-methyl-propyl-sulfonyl, 1,2-trimethyl-propylsulfonyl, 1-ethyl-1-methyl-propylsulfonyl or 1-ethyl-2-methyl-propylsulfonyl; Ci-Cf-alkylidene inoxi: acetylidenaminoxy, 1-propylidene-minoxi, 2-propylidenaminoxy, 1-butylidenaminoxy, 2-butylidenaminoxy or 2-hexylidenaminoxy; Ci-Cs-cycloalkyl means: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl; C3-Cβ-cycloalkoxy means: cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cycloheptyloxy and cyclooctyloxy.

Examples of heterocycles from 3 to 7 members are: oxiranyl, aziridinyl, oxetanyl, tetrahydrofuranyl, tetrahydrothienyl, pyrrolidinyl, isoxazolidinyl, isothiazolidinyl, pirazolidi-nile, oxazolidinyl, thiazolidinyl, imidazolidinyl, dioxola-nil wie l, 3-dioxolan-2-yl and 1,3-dioxolan-4-yl, dioxanyl wie 1,3-dioxan-2-yl, 3-dioxan-4-yl, dithianyl wie 1,3-di-tian-2-yl, des weiteren 1,2 , 4-oxadiazolidinyl, 1,3,4-oxadia-zolidinyl, 1,2,4-thiadiazolidinyl, 1,3,4-thiadiazolidinyl, 1,2,4-triazolidinyl, 1,3,4-triazolidinyl, 2, 3 -dihydrofuryl, 2,5-dihydrofuryl, 2,3-dihydrothienyl, 2,5-dihydrothienyl, 2,3-pyrrolinyl, 2,5-pyrrolinyl, 2,3-isoxazolinyl, 3,4-iso-xazolinyl, 4,5 -isoxazolinyl, 2,3-isothiazolinyl, 3,4-isothiazolinyl, 4,5-isothiazolinyl, 2,3-dihydropyrazolyl, 3,4-dihi-dropirazolyl, 4,5-dihydropyrazolyl, 2,3-dihydrooxazolyl, 3 , 4-dihydrooxazolyl, piperidinyl, tetrahydropyridazinyl, tetrahydropyrimidinyl, 1, 3, 5-tetrahi-drotriacinyl and 1,2,4-tetrahydroth iacinilo, as well as the following heteroaromatics: furyl, such as, for example, 2-furyl and 3-furyl, thienyl, eg 2-tie-nyl and 3-thienyl, pyrrolyl, eg 2-pyrrolyl and 3-pyrrolyl, isoxazolyl, eg . 3-isoxazolyl, 4-isoxazolyl and 5-iso? azo-Lilo, isothiazolyl, eg 3-isothiazolyl, 4-isothiazolyl and 5-isothiazolyl, pyrazolyl, such as 1-pyrazolyl, 3-pyrazolyl and 4 -pyrazolyl, oxazolyl, eg 2-oxazolyl, 4-oxazolyl and 5-oxazolyl, thiazolyl, eg 2-thiazolyl, 4-thiazolyl and 5-thiazolyl, imidazolyl, eg 2-imidazolyl and imidazolyl, oxadiazolyl, eg l, 2,4-oxadiazol-3-yl, 1,2,4-oxadia- 'zol-5-yl and l, 3,4-oxadiazol-2-yl, thiadiazolyl, p .ej., 2,4-thiadiazol-3-yl, 1,4-thiadiazol-5-yl and 1,3,4-thiadia-zol-2-yl, triazolyl, eg 1.2 , 4-triazol-1-yl, 1,2,4-tria-zol-3-yl and 1, 2,4-triazol-4-yl, pyridinyl, eg 2-pyridinyl, 3-pyridinyl and 4-pyridinyl, pyridazinyl, eg 3-pyridinnyl and 4-pyridazinyl, pyrimidinyl, eg 2-pyrimidinyl, 4-pyrimidinyl and 5-pyrimidinyl, furthermore 2-pyrazinyl, 1,3,5-triazin -2-ilo yl, 2,4-triacin-3-il or, especially pyridyl, pyrimidyl, furanyl and thienyl.

All phenyl and heterocyclic rings are preferably unsubstituted or carry a halogen, methyl, trifluoromethyl or methoxy substituent.

With respect to the use of the compounds? d 's the invention of the formula I as herbicides and / or as compounds with defoliating / desiccant action, the variables preferably have the following meanings, by themselves or in combination: A amino or methyl; R hydrogen, fluoro or chloro, especially hydrogen or fluoro; R 2 is halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl or C 2 -C 6 -alkylsulfonyl, especially C 4 -Chaloalkyl, especially trifluoromethyl, chlorodifluoromethyl and pentafluoroethyl; R3 hydrogen or halogen; X oxygen or -N (R7) -, meaning R7 hydrogen or C? -C6-alkyl; ? i, Y2 oxygen; Z oxygen or -N (R8) -; R5, R6, Rβ each independently of the other, hydrogen or Ci-C ^ -alkyl; or R6 and R8 together form a second chemical bond; R4 hydrogen, Ci-Ce-alkyl, C3-Ce-cycloalkyl, Ci-Ce-halogenoalkyl, C3-C6-alkenyl, C3-C6-alkynyl, (C? -C6-l-quil) carbonyl, (C3- C6-alkenyl) carbonyl, (C3-C6-alkynyl) carbonyl or C? -C6-alkylsulfonyl, each of the last 9 radicals mentioned being able to carry, if desired, one or two substituents, each time selected from the group comprising halogen, nitro, cyano, hydroxy, C3-C? -cycloalkyl, C? -C6-alkoxy, Cs-C? -cycloalkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C? -C6-alkoxy-C? C6-alkoxy, Ci-C-l-quiltio, Ci-Cd-alkylsulfenyl, Ci-Cd-alkylsulfonyl, C? -C6-alkylidenaminooxy, a heterocyclyl, heterocyclyloxy, heterocyclylcarbonyl or heterocyclylcarbonyloxy group of 3 to 7 members and with one to three heteroatoms as ring members, selected from the group comprising two oxygen atoms, two sulfur atoms and 3 nitrogen atoms, the heterocycles of which may be saturated or partially or totally unsaturated or aromatic and, if desired, carry one to three substituents in each case selected from the group comprising halogen, nitro, cyano, Ci-Cg-alkyl, C? -C6-alkoxy, Ci- Ce-halogenoalkyl and (Ci-Cβ-alkyl) carbonyl, a group -CO-R9, -O-CO-R9, -CO-OR9, -O-CO-OR9, -CO-SR9, -O-CO-SR9, -CO-N (R9) R10, -0- CO-N (R9) Rl °, -N (R) Rio or -C (NRH) -OR2, where R9 means hydrogen, Ci-Cβ-alkyl, C3-Cβ-cycloalkyl, Cj-Cß-alkenyl, C3-C6-alkynyl, Ci-Cß-alkoxy-C?-C6-alkyl or (C?-C6-alkoxy) ) carbonyl-C? -C6-alkyl, Ri? means hydrogen, hydroxyl, Cj-Cs-alkyl, C3-C8-C-chloroalkyl or Ci-C? -alkoxy, R1] means C? -C6-alkoxy or C3-C6-alkenyloxy R? R- means (C? -C6-alkoxy) carbonyl-C? -C6-alkyl.

Z signifies above all -N (R8) - and R8 together with R6 means a second chemical bond. R4 has, above all, the following meanings: hydrogen, Ci-Cβ-alkyl, C3-Cβ-cycloalkyl, C3-C6 ~ alnyl or C3-Cd-alkynyl, each of the last 4 radicals mentioned can carry one of the following substituents: halogen, nitro, cyano , hydroxy, C3-Cβ-cycloalkyl, Ci-Ce-alkoxy, Cs-Cβ-cycloalkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, Ci-Cg-alkoxy-Ci-Cß-alkoxy, Ci-Cβ -alkylthio, Ci-Cβ-alkylsulfenyl, Ci-Cβ-alkylsulfonyl, C? -C6-alkylidenaminoxy, -C0-OR9, -O-CO-OR9, -CO-N (R9) R10, -0-CO- N (R) RlO or -N (R9) Rl °, wobei R9 is hydrogen, Ci-Cβ-alkyl, C3-Cß-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, C?-C6-alkoxy-C?-C6-alkyl or (Ci-Ce-alkoxycarbonyl) -Ci-Cß-alkyl, R10 is hydrogen or C? -Cd-alkyl.

Especially preferred are the following compounds (X with A = amino, R = fluoro, R 2 = trifluoromethyl, R 3, R 5 and R 6 = hydrogen, X, Y 1, Y 2 and Z = oxygen) indicated in the following table 1: Table 1 ia.81 (CH2) 2-NHCH3 ía.82. { C * H2] 2-MH (CH3): a.83 CH2-OCH3 a.84 CH (CH3) -0CH3 a.85 CH (CH3) -0C2H5 a.86 CH (CH3) CH2-0CH3 a.87 (CH2 ) 20H la.88 CH2-OC2H5 la.89 CH2-COO- (4-acetoxy-tetrahydrofuran-3-yl) la.90 CH2-OCOCH3 a.91 CH2-OCOC2H5 a.92 CH2-C6H5 a.93 ( CH2) 2-C6H5 a.94 CH2- (4-Cl-C6H4) a.95 CH2- (4-CF3-C6H4) a.96 CH2- (3-N02-C6H4) a.97 CH "CH3) C ( NOCH3) CH2C00CH3 In addition, they prefer 151 following 1-arylurates of the formula I: Compounds Ib.01 - Ib.97, which differ from the corresponding compounds la.01 - a.97 only in that R1 signifies hydrogen: the compounds Ic.01 - Ic.97, which differ from the corresponding compounds la.01 - a.97 only in that it means chlorine.

Compounds Id.01 - Id.97, which differ from the corresponding compounds la, 01 - a.97 only in that A means methyl: the compounds le.01-le.97, which differ from the corresponding compounds la.01-a.97 only in that A means hydrogen: compounds If.01 - If.97, which differ from the corresponding compounds la.01 - a.97 only in that A means methyl and R means hydrogen: the compounds Ig.Ol - Ig.97, which differ from the corresponding compounds la.01 - a.97 only in that A and R1 mean hydrogen: the compounds Ih.01 - Ih.97, which differ from the corresponding compounds la.01 - a.97 only in that A means methyl and R1 means chlorine: the compounds Ii.01 - Ii.97, which differ from the corresponding compounds la.01 - a.97 only in that Ri is chlorine and A means hydrogen: compounds Ik.01 - Ik.97, which differ from the corresponding compounds la.01 - a.97 only in that X means -NH-: * R « compounds I1.01 - 11.97, which differ from the corresponding compounds la.01 - a.97 only in that X means -NH- and A means methyl: XR4 the compounds Im.01 - I? U.97, which differ from the corresponding compounds la.01 - a.97 only in that X means -NH- and A means hydrogen: R4 Compounds In.01 - In.97, which differ from the corresponding compounds la.01 - a.97 only. where X means -NH- and R1 means chlorine: the compounds lo.01 - lo.97, ué They differ from the corresponding compounds la.01 - a.97 only in that X means -NH- and A means methyl and Ri means hydrogen: R4 the compounds Ip.01 - Ip.97, which differ from the corresponding compounds la.01 - a.97 only in that X means -NH- and A mean methyl and Rl means chlorine: the compounds Iq.iii - Iq.97, which differ from the corresponding compounds la.01 - a.97 only in that Z means -NH-: Compounds Ir.01 - Ir.97, which differ from the corresponding compounds la.01 - a.97 only, in that Z means -NH- and A signify methyl: ? R4 the compounds Is.Ol-ls.97, which differ from the corresponding compounds la.01 - la. 7 only where Z means -NH- and A means hydrogen: the compounds Iß.01 - lß.97, which differ from the corresponding compounds la.01 - a.97 only in that Z means -NH- and Ri means chlorine: ? R4 compounds It.01 - It.97, which differ from the corresponding compounds la.01 - a.97 only in that Z means -NH- and A means methyl and RI means hydrogen: the compounds Iu.01 - Iu.97, which differ from the corresponding compounds la.01 - a.97 only in that Z means -NH- and A means methyl and R1 means chlorine: compounds Xv.01 - lv.97, which differ from the corresponding compounds la.01 - a.97 only in that X and Z mean both -NH-: compounds Iw.01 - Iw.97, which differ from the corresponding compounds la.01 - a.97 only in that X and Z means n -NH- and A means methyl: the compounds lx.01 - Ix.97, which differ from the corresponding compounds la.01 - a.97 only in that X and Z mean -NH- stehen and A means hydrogen: the compounds ly.01 - Iy.97, which differ from the corresponding compounds la.01 - a.97 only in that X and Z mean -NH- and R1 means chlorine: the compounds Iz.01 - Iz.97, which differ from the corresponding compounds la.01 - a.97 only in that X and Z signify -NH- and A signify methyl and R1 signifies hydrogen: the compounds I? .01 - Í? .97, which differ from the corresponding compounds la.01 - a.97 only in that X and Z signify -NH- and A means methyl and Rl means chlorine: The 3-aryluracils of the formula I can be obtained by different methods, for example, according to one of the following procedures: Process A): Cyclization of an enaminase ester of formula IV or an enamine carboxylate of formula V in the presence of a base: L means lower molecular weight alkyl, preferably C 1 -C 4 alkyl, or phenyl.

As a rule, it is cured in an inert solvent or diluent which is aprotic, for example in an aliphatic or cyclic ether, such as, for example, 1,2-dimethoxyethane, tetrahydrofuran and dioxane, in an aromatic such as, for example, benzene and toluene or in a polar solvent such as, for example, dimethylformamide and dimethyl sulfoxide. Also suitable are mixtures from a polar solvent and a hydrocarbon, such as, for example, n-hexane. Depending on the starting compound, water can also be used as the solvent.

Suitable bases are preferably alkali metal alcoholates, especially sodium alcoholates, alkali metal hydroxides, especially sodium and potassium hydroxide, alkali metal carbonates, especially sodium carbonate and potassium carbonate, and metal hydrides, especially sodium hydride. When using sodium hydride as a base it has proven advantageous to work in an aliphatic or cyclic ether, in dimethylformamide or in dimethyl sulfoxide.

Normally, a quantity of up to 2 molar times of the base is enough with respect to the quantity of IV or V so that the reaction can be carried out successfully.

The reaction temperature varies, generally, from (-78) ° C to the boiling temperature of the corresponding reaction mixture, especially from (-60) to 60 ° C. i When A in formula III or IV means hydrogen, then the product of the process is obtained as a metal salt, corresponding the metal to the cation of the base used. The salt can be isolated in a known manner or can be formed by an acid in the free compound I with A = hydrogen.

Procedure B > : Methylation of a compound I, wherein A means hydrogen, in the presence of a base: R4 R4 I (A = H) I (A = CH3) Suitable methylation agents are methyl halides, preferably methyl chloride, methyl iodide or methyl bromide, as well as dimethyl sulfate, methanesulphonate. { methyl mesylate), methyl benzene sulfonate, p-to-luenesulfonylmethane (methyl tosylate), p-bromobenzenesulfonylmethane (methyl brosylate), trifluoromethanesulfonylmethane (methyl triflate) and diazomethane.

In general, the reaction is carried out in an inert organic solvent, for example in a protic solvent, such as, for example, lower alcohols, preferably in ethanol, optionally in a mixture with water, or in an aprotic solvent, for example in an ether. aliphatic or cyclic, preferably in 1,2-dimethoxy-tan, tetrahydrofuran or dioxane, in an aliphatic ketone, preferably in acetone, in an amide, preferably in dimethylformamide, in a sulfoxide, preferably in dimethyl sulfoxide, in a urea as a tetramethylurea and 1, 3-dimethyltetrahydro2 (1H) -pyrimidinone, in a carboxylic ester, such as, for example, ethyl acetate, or in a halogenated aliphatic or aromatic hydrocarbon, such as, for example, dichloromethane and chlorobenzene.

Suitable bases are inorganic bases, eg carbonates, such as sodium carbonate and potassium carbonate, hydrocarbonates, such as sodium and potassium hydrogencarbonate, or alkali metal hydrides, such as, for example, sodium hydride. and potassium hydride, as well as organic bases, eg, amines such as, for example, triethylamine, pyridine and N, N-diethylaniline, or alkali metal alcoholates, such as, for example, sodium methanolate, sodium ethanolate and tere. -postassium butanolate.

The amount of the base and the methylating agent is preferably 0.5 to 2 times the molar quantity, based on the quantity of the starting compound.

The reaction temperature varies, generally, from (-78) ° C to the boiling temperature of the reaction mixture, especially from (-60) to 60 ° C.

A preferred variant consists of methylating the salt I from the cyclization of IV (A = H) or V (A = H) according to process A) without isolation of the reaction which may still contain excessive base, eg Sodium hydride, sodium alcoholate or sodium carbonate.

Provided that they can not be obtained directly by means of the cyclization under the basic conditions described as method A), the salts of those compounds, in which A means hydrogen, can also be obtained in a manner known per se from the products of the process according to method A. For which, for example, the aqueous solution of an inorganic or organic base is mixed with the substituted 3-aryluracil I, in which A means hydrogen. Normally, the formation of the salt takes place with enough speed already at 20-25nC.

It is particularly advantageous to prepare the sodium salt by solution of the 3-aryluracil I (A = hydrogen) in aqueous sodium hydroxide solution at 20-25 ° C, with approx. equivalents of 3-aryluracil and sodium hydroxide. The 3-aryluracil salt can then be isolated, for example by precipitation with a suitable inert solvent or by evaporation of the solvent.

The salts of the 3-aryluracils, whose metal ions are not alkali metal ions, can normally be obtained by recrystallization of the corresponding alkali metal salt in aqueous solution. In this way, for example, the metal salts of 3-aryluracil that are insoluble in water can be obtained.

Procedure C: Reaction of a 3-aryluracil of the formula I, wherein A means hydrogen, with an amination reactive, in the presence of a base: \ \? R4 R4 I (A = H) I (A = NH2) 2,4-dinitrophenoxyamine has been especially accredited as an amine-containing reagent, but the hydroxylamine of O-sulfonic acid (HOSA) known from the literature can also be used as a reagent of amination (see, eg, E. Hofer et al., Synthesis 1983, 466, W. Friedrichsen et al., Heterocycles Q. (1983) 1271, H. Hart et al., Tetrahedron Lett. 25 (1984) 2073; B. Vercek et al., Monatsh, Chem. 114 (1983) 789; G. Sosnousky et al., Z. Naturforsch. 3L (1983) 884; RS Atkinson et al., J. Chem. Soc. Perkin Trans. 1987, 2787).

The amination is carried out in a known manner (see, for example, T. She-radsky, Tetrahedron Lett, 1968, 1909, MP Wentland et al., J. Med. Chem. 21 (1984) 1103 and especially EP-A 240 194. , EP-A 476 697 and EP-A 517 181, where the amuration of uraci-los is taught).

Normally, it is carried out in a polar solvent, for example in dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide or in ethyl acetate, which to date has proved to be very suitable.

Suitable bases are, for example, alkali metal carbonates such as, for example, potassium carbonate, alkali metal alcoholates, such as, for example, sodium methylate and post-tertiary tert-butanolate, or alkali metal hydrides, such as, for example, sodium hydride. .

In each case, the amount of the base and the aminating agent is preferably 0.5 molar to 2 molar, based on the amount of the starting compound.

Depending on the importance of R4 it may be necessary to protect this substituent in a manner known per se against amination. This is even more advisable when R4 means hydrogen.

Method D): Sulfurization of a 3-aryluracil of the formula I with Y x = oxygen: I (Yl = 0) I (Y! = S) The sulfurization is generally carried out in an inert solvent or diluent, for example, in an aromatic hydrocarbon, such as, for example, toluene and the xylenes, in an ether such as, for example, diethyl ether, 1,2-dimethoxyethane. and tetrahydrofuran, or in an organic amine, such as, for example, pyridine.

As sulphidation reagent, phosphorus sulphide (V) and 2,4-bis (4-methoxyphenyl) -1,3,2,4-dithiphosphine-2,4-dithione ("reagent") are particularly suitable. Lawes-son ").

It is generally sufficient to use an amount of 1 to 5 molar times with respect to the starting compound to be sulfurized, in order to obtain a complete transformation.

The reaction temperature is usually at 20 to 200 ° C, preferably at 40 ° C up to the boiling temperature of the reaction mixture.

In the sulfurization of starting compounds in which Y1 and Y2 mean oxygen, products can be formed with both? I = sulfur and also with Y2 = sulfur. The purely useful products which are desired in each case are usually isolated, then from the reaction mixtures which may still contain starting material, with the aid of conventional separation techniques, such as, for example, crystallization and chromatography.

Procedure E > : The alkylation of a 3-aryluracil of the formula I, wherein R 4 means hydrogen, in the presence of a base: I (R4 = unsubstituted alkyl, cycloalkyl, alkenyl or alkynyl or substituted H I (R4 = H) The alkylation can be carried out, for example, with the halide, preferably the chloride or bromide, the sulfate, the sulfonate, preferably the methanesulfonate (mesylate), benzenesulfonate, p-toluenesulfonate (tosylate), p-bromobenzenesulfonate (brosylate), trifluoromethanesulfonate (triflate) or the diazo compound of an unsubstituted alkane, cycloalkane, halogenoalkane, alkene or alkyne or substituted.

Normally, it is used here in an inert organic solvent, with protic solvents, such as, for example, lower alcohols, preferably ethanol or a mixture from ethanol and water, as well as aprotic solvents, for example, being suitable. aliphatic or cyclic ethers, such as 1,2-dimethoxyethane, tetrahydrofuran and dioxane, aliphatic ketones, such as acetone, amides such as dimethylformamide, sulphoxides such as dimethyl sulfoxide, ureas, such as, for example, tetramethylurea and 1,3-dimethyltetrahydro-2 (1H) -pyrimidinone, the carboxylic esters, such as ethyl acetate or the halogenated aliphatic or aromatic hydrocarbons, such as, for example, dichloromethane and chlorobenzene.

Suitable bases are inorganic bases, eg alkali metal carbonates, such as, for example, sodium carbonate and potassium carbonate, alkali metal hydrogencarbonates, such as sodium and potassium hydrogencarbonate, or hydride hydrates. alkali metals such as, for example, sodium hydride and potassium hydride, as well as organic bases, eg amines, such as triethylamine, pyridine and N, N-diethylaniline, or alkali metal alcoholates, such as, for example, methanolate Sodium, sodium ethanolate and post-tetasium tert-butanolate.

The amount of the base and the alkylating agent is preferably 0.5 to 2 times the molar amount, with respect to the amount of I with R 4 = hydrogen.

It is generally advisable to apply a reaction temperature of (-78) ° C to the boiling temperature of the reaction mixture, especially (-60) to 60 ° C.

Possible problems of regioselectiVity in the starting compounds with A = hydrogen can be avoided in a manner known per se (use of 2 equivalents of the base, introduction of a protectant group, etc.).

Procedure F > The acylation of a 3-aryluracil of the formula I, where R 4 signifies hydrogen, with an appropriate acylating agent: alkylcarbolenecarbonylcarbonate sust. or I (R4 = H) Suitable acylating agents are, for example, acid halides, especially acid chlorides, anhydrides, isocyanates or sulfonyl chlorides of alkane-, alkenyl- or alkynecarboxylic acids. However, free acids or their anhydrides are also suitable, provided that they work in the presence of a condensing agent, such as, for example, carbonyldiimidazole and dicyclohexylcarbodiimide.

As a rule, the reaction is carried out in an inert organic solvent or diluent, which is preferably aprotic, for example in an aliphatic or cyclic ether, such as, for example, 1,2-dimethoxyethane, tetrahydrofuran and dioxane, an aliphatic ketone, eg acetone, an amide, such as, for example, dimethylformamide, a urea such as, for example, tetramethylurea and 1,3-dimethyltetrahydro-2 (1H) -pyrimidinone, a carboxylic ester such as, for example, acetate of ethyl, or a halogenated aliphatic or aromatic hydrocarbon, such as, for example, dichloromethane and chlorobenzene.

With respect to the appropriate bases and quantitative relationships as well as the reaction temperature, refer to the explanations described in Procedure E).

Process G): The halogenating of a 3-aryluracil of the formula I, wherein R 3 means hydrogen: R4 R4 I (R3 = H) I (R3 = halogen) The halogenation is generally carried out in an inert organic solvent or diluent. Suitable chlorination or bromination are, for example, aliphatic carboxylic acids, such as acetic acid, or chlorinated aliphatic hydrocarbons, eg, methylene chloride, chloroform and carbon tetrachloride. Especially preferred for iodination are low-boiling aliphatic carboxylic acids, such as, for example, acetic acid.

Chlorine or elemental bromine, or sulfuryl chloride or bromide, at a reaction temperature of preferably 0 to 60 ° C, especially 10 to 30 ° C, are particularly suitable for chlorination and bromination.

If desired, chlorination and bromination can be carried out in the presence of an acid acceptor, with sodium acetate and tertiary amines being preferred, such as, for example, triethylamine, dimethylaniline and pyridine.

As the iodinating agent, elemental iodine is particularly preferred, in which case the reaction temperature is brought to approx. 0 to 110 ° C, preferably at 10 to 30 ° C.

It is particularly advantageous to carry out the iodination in the presence of a mineral acid, such as, for example, fuming nitric acid.

The amount of halogenation agent is not critical; Normally, equimolar amounts of halogenating agent or an excess of up to approx. 200% in mol, with respect to the starting compound (I with R4 = hydrogen).

Excessive iodine can be removed after the reaction by saturated aqueous solution of sodium hydrogensulfite.

Method H): The amination of a heterocyclic compound of the formula VI in the presence of a base: VI I (X = NH, R4 = H)) For more details about carrying out this procedure, please refer to the explanations indicated for Procedure C).

When VI is used with A = hydrogen, the VI and / or I with A = amino can also be obtained together with the desired useful products I (with XR4 = NH2). In these cases it is advisable to influence the course of the reaction by the usual methods for this purpose (use of 2 equivalents of the base, incorporation of a protective group, etc.), so that the desired product is obtained pre-dominantly .

Method K): The reduction of nitro compounds of formula VII in hydroxyl amines VIII and subsequent cyclization of VIII giving I: VII VIII Cyclization VIII I (X = 0; R4 = H) L: - represents low molecular weight alkyl, preferably C) - C4-alkyl or phenyl.

For conventional reduction, conventional reductants, such as, for example, tin (II) and iron salts, or preferably molecular hydrogen in the presence of a catalyst, such as, for example, platinum on carbon, are suitable.

When using hydrogen, it is advisable to work in a tertiary amine, such as, for example, N-methylmorpholine as a solvent.

Conveniently, a pressure of hydrogen of normal pressure will be worked up to 10 bar of overpressure.

Generally, the reduction can be carried out successfully at temperatures from (-5) to + 50 ° C.

The hydroxylamines VIII are new. Its cyclization giving I occurs, frequently, already at slightly elevated temperatures, as they are usually applied for the concentration of reaction solutions. Therefore, it is particularly advantageous to reduce to VII and cyclize the product of process VIII without prior isolation of the reaction mixture.

The compounds I obtained can be isolated and purified by known methods.

The enamine esters of formula IV are new. They can be obtained by methods known per se, for example according to one of the following methods: Preferably, work is carried out essentially in the absence of water in an inert solvent or diluent, particularly preferably in the presence of an acid or basic catalyst.

Suitable solvents or diluents are organic solvents which are miscible with water in the form of azeotropes, for example aromatics, such as benzene, toluene and o-, m-, p-xylene, halogenated hydrocarbons such as, for example, methylbenzene chloride. , chloro-sulfur, carbon tetrachloride and chlorobenzene, aliphatic and cyclic ethers, such as, for example, 1,2-dimethoxyethane, tetrahydrofuran and dioxane, or cyclohexane, but also alcohols such as, for example, methanol and ethanol.

Suitable acid catalysts are, in particular, the strong mineral acids, such as sulfuric acid and hydrochloric acid, the phosphorus-containing acids, such as, for example, orthophosphoric acid and polyphosphoric acid, the arganic acids, such as the toluenesulfonic, as well as acid ion exchangers, such as "Amberlyst 15" (Fluka).

Suitable basic catalysts are, for example, metal hydrides, such as sodium hydride, as well as metal alcoholates which are especially preferred, such as, for example, sodium methanolate and sodium ethanolate.

Conveniently IX and ß-keto ester X are used in an approx. stoichiometric or working with a small excess of one or the other component up to approx. 10% in mol.

Normally, it suffices to use the catalyst in an amount of 0.5 to 2 mol%, with respect to the amount of an educt.

Generally, the reaction is carried out at a temperature of 60 to 120 ° C to rapidly remove the water formed, preferably at the boiling temperature of the reaction mixture.

M) L3 means C? -C4-alkyl or phenyl.

This reaction can be carried out, for example, in an organic solvent miscible with water, such as an aliphatic or cyclic ether, such as, for example, 1,2-dimethoxyethane, tetrahydrofuran and., Dioxane, or a lower alcohol, especially ethanol, with the reaction temperature usually rising to 50 to 100 ° C, preferably at the boiling temperature of the reaction mixture.

The reaction can also be carried out in an aromatic diluent, such as, for example, benzene, toluene and o-, m-, p-xylene, in which case it is advisable to add either an acid catalyst, such as, for example, hydrochloric acid and p-toluenesulfonic, or base dune, eg, an alkali metal alcoholate, such as, for example, sodium methanolate and sodium ethanolate. Also in this process variant, the reaction temperature is normally raised to 50 to 100 ° C, but preferably to 60 to 80 ° C.

With respect to the quantitative relationships, the data indicated for method L) is valid.

N) The reaction is suitably carried out in the presence of an essentially anhydrous organic or aprotic solvent or diluent, for example an aliphatic or cyclic ether, such as diethyl ether, 1,2-dimethoxyethane, tetrahydrofuran and dioxane, a hydrocarbon. aliphatic or aromatic, such as, for example, n-hexane, benzene, toluene and o-, m-, p-xylene, a halogenated aliphatic hydrocarbon, such as, for example, methylene chloride, chloroform, carbon tetrachloride, 1,2- dichloroethane and chlorobenzene, a polar aprotic solvent, such as, for example, dimethylformamide, hexamethylphosphoric acid triamide and dimethyl sulfoxide, or in a mixture of the solvents mentioned.

If desired, it is also possible to work in the presence of a metal hydride base, such as, for example, sodium and potassium hydride, alkali metal or alkaline earth metal alcoholate, such as, for example, sodium methanolate, sodium ethanolate and tert. .-potassium butanolate, or in a tertiary organic base, such as, for example, triethylamine and pyridine, the organic base serving at the same time as a solvent.

Conveniently, the educts are used in an este-qui-etric ratio, or work with a slight excess of either component up to approx. 10% in mol. When working without solvent in the presence of an organic base, then it will be present in a greater excess.

The reaction temperature varies, preferably, from (-80) to 50 ° C, especially from (-60) to 30 ° C.

In an especially preferred variant, the obtained IV enaminase ester is converted with an excess of a base directly (ie "in situ") according to Process A) into the useful product I.

Possible byproducts (eg, C-alkylation products in compounds where R3 means hydrogen), can be removed according to conventional separation methods, such as crystallization and chromatography.

O): L 4 is C 4 -C 4 alkyl or phenyl.

This reaction is conveniently carried out in a solvent or polar aprotic diluent, such as, for example, dimethylformamide, 2-butanenone, dimethyl sulfoxide and acetoneitrile, namely, preferably in the presence of a base, for example an alkanolate of alkali metal or alkaline earth metal, especially a sodium alkanolate, such as sodium methanolate, an alkali metal or alkaline earth metal carbonate, especially sodium carbonate, or eines of an alkali metal hydride, such as, for example, lithium hydride and sodium hydride.

Normally, a quantity of 1 to 2 molar times of the base is enough, with respect to the quantity of XI or XIII.

The reaction temperature is generally 80 to 180 ° C, preferably at the boiling point of the reaction mixture.

With regard to the quantitative ratios of the starting compounds, the data given for method L) are valid.

In a particularly preferred variant, a sodium alcoholate is used as the base and the alcohol formed continuously is distilled in the course of the reaction. The IV ester enamins obtained in this way can be cyclized to obtain them without isolating them from the reaction method, using Method A), giving a salt of the 3-aryluracils I.

P): This reaction is conveniently carried out in the presence of an essentially anhydrous organic or aprotic solvent or diluent, for example an aliphatic or cyclic ether, such as diethyl ether, 1,2-dimethoxyethane, tetrahydrofuran and dioxane, an aliphatic hydrocarbon. or aromatic, such as, for example, n-hexane, benzene, toluene and o-, m-, p-xylene, a halogenated aliphatic hydrocarbon, such as, for example, methylene chloride, chloroform, carbon tetrachloride, 1,2-dichloroethane and chlorobenzene, a polar aprotic solvent, such as, for example, dimethylformamide, hexamethylphosphoric acid triamide and dimethyl sulfoxide, or in a mixture of the solvents mentioned.

If desired, it is also possible to work in the presence of a metal hydride base, such as, for example, sodium and potassium hydride, alkali metal or alkaline earth metal alcoholate, such as, for example, sodium methanolate, sodium ethanolate and tert. .-potassium butanolate, or in a tertiary organic base, such as, for example, triethylamine and pyridine, the organic base serving at the same time as a solvent.

Conveniently, the educts are used in an este-quimetric ratio, or they work with a slight excess of one or the other component of up to approx. 20% in mol. When working is solvent in the presence of an organic base, then it will be present in a greater excess.

The reaction temperature generally varies from (-30) to 150 ° C, preferably from (-30) up to the boiling temperature of the corresponding reaction mixture.

The enamine carboxylates of formula V are also new; they can be obtained in a manner known per se, for example, from the aniline derivatives of the formula XV, according to the following reaction scheme: III XVIII The reaction of XV with XVI is carried out, preferably in an anhydrous inert aprotic solvent, for example in a halogenated hydrocarbon, such as methylene chloride, chloroform, carbon tetrachloride and chlorobenzene, in an aromatic hydrocarbon, such as, for example, benzene, toluene and o-, m-, p-xylene, or in an aliphatic or cyclic ether, such as, for example, diethyl ether, dibu-tyl ether, 1,2-dimethoxyethane, tetrahydrofuran and dioxane.

The reaction temperature varies in this reaction (from XV to XVI), generally of approx. 70 to 140 ° C, especially from 100 to 120 ° C.

The reaction of XV with XVII is an aminolysis which is generally carried out in or without solvent [see, eg, J. Soc. Dyes Col. 4., 81 (1926), Ber. £ i, 970 (1931); Org. Synth., Coll. Vol. IV, 80 (1963) and J.A.C.S. ___., 2402 (1948)] or in an anhydrous inert solvent / diluent, especially in an aprotic solvent, for example in an aromatic, such as toluene and o-, m-, p-xylene or in a halogenated aromatic, as p .ej chlorobenzene.

Here it is advisable to work in the presence of a basic catalyst, for example a high-boiling amine [see, for example, Helv. Chim. Acta 11, 779 (1928) and U.S. 2,416,7381 or pyridine.

The reaction temperature is preferably at parox. 20 to 160 ° C.

Conveniently, the starting compounds will be added in amounts of approx. stoichiometric or will work with a lei-gero excess of one or another component of up to approx. 1% in mol. When working in the presence of a basic catalyst, then usually a quantity of catalyst of from 0.5 to 200 mol% is sufficient with respect to the amount of one of the educts.

The subsequent reaction of the compounds thus obtained of formula XVIII with the amine H2N-COOL is advantageously carried out in a substantially anhydrous solvent / diluent at nominal pressure, especially in the presence of an acid catalyst.

Suitable solvents / diluents are water-miscible liquids in the form of azeotropes, for example aromatics such as, for example, benzene, toluene and o-, m-, p-xylene or halogenated hydrocarbons, such as, for example, carbon tetrachloride and chlorobenzene.

Suitable catalysts are, in particular, strong mineral acids, such as, for example, sulfuric acid, organic acids, such as, for example, p-toluenesulfonic acid, phosphorus-containing acids, such as, for example, orthophosphoric acid and polyphosphoric acid. or acidic exchangers, such as "Amberlyst 15" (Fluka).

The reaction temperature is generally approx. 70 up to 150 ° C; but to quickly remove the reaction water formed, it will conveniently be worked at the boiling temperature of the respective reaction mixture.

The compounds of formula X, XII and XIII are also new. They can also be obtained in a manner known per se and, in a particularly advantageous manner, from compounds of the formula XV by: Q) "Phosgenation" of compounds of formula XV and hydrolysis of the products of process XII with ammonia derivatives: COCÍ- or ClCOOCCli The process can be carried out in an inert, substantially anhydrous solvent or diluent / solvent. The compounds XV are preferably reacted here with phosphene or trichloromethyl chloroformate.

Suitable solvents / diluents are, in particular, aprotic organic solvents, for example aromatics, such as toluene and o-, m-, p-xylene, halogenated hydrocarbons, such as, for example, methylene chloride, chloroform, 1,2-dichloroethane and chlorobenzene, aliphatic or cyclic ethers, such as, for example, 1,2-dimetho-ethane, tetrahydrofuran and dioxane, or esters, such as, for example, ethyl acetate, as well as mixtures of these solvents.

Depending on the aniline derivative XV used, it may be advantageous to add a base, such as, for example, triethylamine in an amount of 0.5 to 2 molar times, with respect to the amount of XV.

The phenyl isocyanates XII are usually formed at the reaction temperature of 50 ° C up to the boiling temperature of the reaction mixture; they can be subsequently transformed with ammonia or a reactive derivative of ammonium, giving the phenylurea X derivatives.

Reaction of alkali metal cyanates: Mf OCN0 XV X M® represents the equivalent of a metal ion, especially an alkali metal ion, such as, for example, sodium and potassium.

The reaction is generally carried out in an inert solvent / diluent, for example in an aromatic hydrocarbon, such as, for example, toluene and the xylenes, in an aliphatic or cyclic ether, such as, for example, tetrahydrofuran and dioxane, a lower alcohol, such as, for example, methanol and ethanol, in water or in a mixture of the solvents mentioned i The amount of cyanate is not critical; to achieve a complete transformation, at least the equimolar amount of the aniline derivative XV and the cyanate is needed, but it may also be advantageous to use the cyanate in an amount of up to approx. 100% in mol.

The reaction temperature is, as a rule, at 0 ° C up to the boiling temperature of the re-action mixture.

Reaction with ístereß L0-CO-L5: L5 means halogen, preferably chlorine or bromine, C? -C4-alkoxy or phenoxy.

Suitable solvents / diluents are, for example, aromatic hydrocarbons, for example toluene and the like, halogenated hydrocarbons, such as, for example, methyl chloride, chloroform, 1,2-dichloroethane and chlorobenzene, the aliphatic ethers or cyclic compounds, such as, for example, 1,2-dimethoxyethane, tetrahydrofuran and dioxane, esters, such as, for example, ethyl acetate, alcohols such as, for example, methanol and ethanol, or water or mixtures thereof. an organic solvent and water.

Preferably, the reaction will be carried out in the presence of a base, eg an alkali metal hydroxide, carbonate or alcoholate, such as, for example, sodium hydroxide, sodium carbonate, methanolate and sodium ethanolate, or a tertiary amine, such as e.g. eg, pyridine and triethylamine.

If it is dried, a catalyst, eg, a Lewis acid, such as antimony trichloride, can also be added.

Conveniently, the starting compounds and the base will be used in amounts of approx. stoichiometric, but it is also possible to present the one or the other component in an excess of up to approx. 100% in mol.

Generally, the amount of the catalyst will be increased to 1 to 50 mol%, preferably 2 to 30 mol%, based on the amount of the aniline derivative XV used.

The reaction can be carried out normally, at a reaction temperature of (-40) ° C up to the boiling temperature of the reaction mixture.

The starting compounds of the formulas VI and VII are known or can be obtained in a manner known per se (see, for example, EP-A 420 194, EP-A 408 382, U.S. 5,310,723 and WO 90/15057).

The aniline derivatives of the formula XV are also conical or can be obtained according to known processes (see especially EP-A 477 677).

Unless otherwise indicated, all the described procedures are carried out, conveniently, at atmospheric pressure or at the proper pressure of the respective reaction mixture.

Depending on the respective substitution sample of the compounds to be obtained, it may be advisable to change the order of the different reaction stages, in order to avoid obtaining certain secondary products or to obtain them only in small quantities.

The further processing of the reaction mixtures is carried out according to known methods, for example by removing the solvent, distributing the residue in a mixture from water and an appropriate organic solvent and elaborating the organic phase further to obtain the product.

The 3-aryluracils of the formula I can contain one or several centers of chirality and are usually obtained in the form of enatomeric or diastereomeric mixtures, provided that no specific synthesis is carried out to obtain an isomer. The mixtures can be separated, if desired, according to the methods known for this purpose, eg, by chromatization or chromatography on an optically active adsorbate, then the substantially pure isomers are obtained. Optically active isomers can be prepared, for example, also from the corresponding optically active starting materials.

The 3-aryluracils I, in which A means hydrogen, can be converted in a manner known per se into their salts, preferably into their alkali metal salts.

The salts of I, whose metal ions are not alkali metal ions, can be prepared by recrystallization of the corresponding alkali metal salt in a customary manner; The same goes for the ammonium, phosphonium, sulphonium and sulfoxonium salts by means of ammonia, hydroxides of sosphonium, sulfonium or sulfoxonium.

The compounds I and their salts useful in 1 = agricualture are suitable - both in the form of isomeric mixtures, and also in the form of pure isomers - and herbicides. The herbicidal products containing I are well suited for controlling the growth of plants in areas not intended for cultivation, especially in high amounts of application. In crops such as wheat, rice, corn, soybeans and cotton they are active against weeds and unwanted grasses without causing damage worthy of mention in crop plants. This effect is achieved above all with low amounts of application.

Depending on the respective application method, the compounds I or the herbicidal products containing them can be used in other plant crops to destroy unwanted plants in them. For example, the following crops come into consideration: Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Beta vulgaris spp. altissima, Beta vulgaris spp. rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. silvestris, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus lemon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linu usitatissimum, Lycopersicon lycopersicum, Malus spp., Manihot esculenta, Medicago sativa. Musa spp., Nicotiana tabacum (N. rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spp., Pisu sativum, Prunus avium, Prunus persica, Pyrus com unis, Ribes sylvestre, Ricinus communis, Saccharum offici-narum, Sécale cereale, Solanum tuberosum, Sorghum bicolor (S. vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera, Zea mays.

In addition, compounds I can also be used in crops, which by means of culture methods and / or genetic technology methods have become substantially resistant against the action of herbicides.

They are also suitable for the desiccation and / or defoliation of plants.

As desiccants they are particularly suitable for drying the surface parts of crop plants, such as potatoes, rapeseed, sunflower and soybeans. Allowing in this way a fully mechanized harvest of these important crop plants.

Also has economic importance facilitating the harvest through a concentrated fall in a given time or reducing adhesion to the tree in case of citrus fruits, olives or other species of stone fruit and peels of pepas . The same mechanism, namely the facilitation of the formation of separating tissue between the fruit or the leaf and the germ of the plant is also essential for a controlled defoliation of useful plants, especially cotton.

Also, the shortening of the interval d? Time, when the cotton plants are mature, results in a higher fiber quality after collection.

The compounds I or the herbicidal products containing them can be used in the form of solutions, powders, suspensions, also in the form of highly concentrated aqueous, oleic or other suspensions or dispersions, or in the form of emulsions, oil dispersions. , pastes, spraying agents, spraying agents, directly pulverisable granules, by spraying, spraying, spraying or spraying. The forms of application depend entirely on the respective application purposes; in all cases, the finest possible distribution of the active substances of the invention must be ensured. inert excipients suitable for producing solutions, emulsions, pastes or oil dispersions directly sprayable are essentially: mineral fractions aciete point to high boiling medium, eg diesel oil and kerosene also oils coal tar and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, paraffins eg te-trahidronaftalina, alkylated naphthalenes and their derivatives, alkylated benzenes and their derivatives, alcohols such as methanol, ethanol, n-propanol, butanol and cyclohexanol, ketones, such as cyclohexamone, strongly polar solvents, eg amines, such as N-methylpyrrolidone and water.

The aqueous application forms can be prepared from emulsion concentrates, dispersion, pastes, wettable powders or granules dispersible in water, by the addition of water. To obtain emulsionen} In the case of oil spreads or dispersions, the substrates can be homogenized as such or dissolved in an oil or solvent, by means of wetting agents, adhesives, dispersants or emulsifiers, in water. However, it is also possible to prepare concentrates which consist of the active substance, the humectant, the adhesive, the dispersant or the emulsifier and, optionally, a solvent or oil, and which are suitable for being diluted with water.

Suitable surface-active substances (additives) are alkali metal, alkaline earth metal, ammonium salts of aromatic sulphonic acids, for example lignin sulphonic acid, naphthalenesulfonic acid, phenolsulfonic acid and dibutylnaphthalene sulphonic acid, as well as fatty acids of alkyl and alkylaryl sulphonates. , alkyl and lauryl ether sulfonates and sulphonates of fatty alcohols, as well as their alkali and alkaline earth salts of hexa, hepta and octadecanols, as well as of ethers of fatty alcohols, of condensation products from naphthalene and their derivatives with formaldehyde, of condensates of naphthalene or of naphthalenesulfonic acids with phenol, formaldehyde, polyoxyethylene-octylphenol ethers, isooctylphenol, octylphenol or nonylphenol ethoxylates, alkylphenol polyglycol ethers, tributylphenylpolyglycol ethers, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol-ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ether it is either polyoxypropylene, acetal polyglycol ether lauryl alcohol, sorbitol esters, sulphite residual liquors and methylcellulose.

The powders, spraying or spraying agents can be obtained by mixing or co-grinding the active substances with a solid support.

Granules, eg coated, impregnated or homogeneous granules can be prepared by binding the active substances to a solid support. Solid substrates are mineral soils, such as silicic acids, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium sulfate and magnesium sulfate, magnesium, ground plastics, fertilizers, such as eg ammonium sulfate, ammonium phosphate, ureas and vegetable products, such as cereal flours, tree bark powders, wood powders and nutshell powders, cellulose powders or other solid supports.

The concentration of active substances I in ready-to-use preparations can vary over a wide range of ca. 0.001 to 98% by weight, preferably 0.01 to 95% by weight. The active substances are used here, usually in a purity of 90% up to 100%, preferably 95% up to 100% (according to the NMR spectrum).

The following formulation examples illustrate the preparation of such preparations: I. 20 parts by weight of compound No. 1.03 are dissolved in a mixture composed of 80 parts by weight of alkylated benzene, 10 parts by weight of the addition product of 8 to 10. moles of ethylene oxide to 1 mole of oleic acid N-monoethanolamide, 5 parts by weight of the calcium salt of dodecylbenzenesulfonic acid and 5 parts by weight of the addition product of 40 moles of ethylene oxide to 1 mole of oil of castor By pouring and finely distributing the solution in 100 000 parts by weight of water, an aqueous dispersion containing 0.02 parts by weight of the active substance is obtained.

II. 20 parts by weight of compound No. 1.04 are dissolved in a mixture composed of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the addition product of 7 moles of ethylene oxide to 1 mol of isooctylphenyl and 10 parts by weight of the addition product of 40 moles of ethylene oxide n 1 mole of castor oil. By pouring and finely distributing the solution in 100 000 parts by weight of water, an aqueous dispersion containing 0.02 parts by weight of the active substance is obtained.

III. 20 parts by weight of the active substance No. 1.06 are dissolved in a mixture composed of 25 parts by weight of cyclohexanone, 65 parts by weight of a mineral oil fraction of boiling point 210 to 280 ° C and 10 parts by weight of the addition product give 40 moles of ethylene oxide to 1 mole of castor. By pouring and finely distributing the solution in 100 000 parts by weight of water, an aqueous dispersion containing 0.02 parts by weight of the active substance is obtained.

IV. 20 parts by weight of active substance No. 1.07 are ground in a hammer mill together with 3 parts by weight of the sodium salt of diisobutylnaphthanesulfonic acid, 17 parts by weight of the sodium salt of a lignin acid of a sulphite residual liquor and 60 parts by weight of powdery silicagel. By pouring and finely distributing the solution in 20,000 parts by weight of water, an aqueous dispersion containing 0.1 parts by weight of the active substance is obtained. 3 parts by weight of the active substance No. 1.08 and 97 parts by weight of finely particulate kaolin. In this way, a spray agent containing 3% by weight of the active substance is obtained.

SAW. 20 parts by weight of the active substance No. 1.09 are mixed intimately with 2 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, 8 parts by weight of the polyglycol ether fatty alcohol, 2 parts by weight of the sodium salt of a phenol condensate - urea-formaldehyde and 68 parts by weight of a paraffinic mineral oil. Stable dispersion is obtained.

VII. 20 parts by weight of compound No. I.10 are dissolved in a mixture consisting of 70 parts by weight of cyclohexanone, 20 parts by weight of isooctylphenol and 10 parts by weight of ethoxylated castor oil. An emulsion concentrate is obtained. stable.

VIII 1 part by weight of compound No. I.11 are dissolved in a mixture from 80 parts by weight of cyclohexanone and 20 parts by weight of Emulphor EL1 *. A stable emulsion concentrate is obtained. ethoxylated castor oil (castor oil) Active substances or herbicide products can be applied before or after the emergency. When the active substances are less tolerated by certain crop plants, then application techniques are used, in which the herbicidal products are sprayed by sprayers in such a way that they do not reach the leaves of the sensitive crop plants, but they do on the leaves of the unwanted plants that grow under them or on the uncovered ground surface (post-directed, lay-by).

The amounts of active substance vary according to the purpose of application, the season and the growth stage of 0.0001 to 3.0, preferably 0.01 to 1.0 kg / ha of active substance (s.a.).

To broaden the spectrum of action and to achieve synergistic effects, the 3-aryluracils I can be mixed with numerous representatives of other herbicidal active substances and growth regulators, and be applied in conjunction with these. Compounds such as, for example, 1,2,4-thiadiazoles, 1,3,4-thiadiazoles, amides, aminophosphoric acid and its derivatives, aminotriazoles, anuides, aryloxy- / heteroaryloxyalkanoic acids and dus -vados, the benzoic acids and their derivatives, the benzothiadia-zinones, 2- (hetaroyl / aroyl) -l, 3-cyclohexandiones, heteroaryl-aryl-ketones, benzisoxazolidinones, the derivatives of me-ta-CF3-phenyl, carbamates, quinolinecarboxylic acids and their derivatives, chloroacetanilides, cyclohexane-1, 3-dione derivatives, diacins, dichloropropionic acid and its derivatives, dihydrobenzofurans, dihydrofuran-3-ones, dinitropanilines, dinitrophenols, diphenyl ethers, dipyridyls, halogenated carboxylic acids and their derivatives, ureas, 3-phenyluracils, imidazoles, imidazolinones, N-phenyl-3,4,5,6-tetrahydrophthalimides, oazoles, oxiranes, phenols, esters of aryloxy- and heteroaryloxyphenoxy-pionic, phenylacetic acid co and its derivatives, 2-phe nylpropaneic acid and its derivatives, pyrazoles phenylpyrazoles, pyridazinase, pyridinecarboxylic acid and its derivatives, pyrimidyl ether, sulfonamides, sulfonylureas, triazines, triazinones, triazolinones, triazolecarboxamides and uracils.

In addition, it may be useful to apply the compounds I on their own or in combination with other herbicides, also in admixture with other plant protection products, for example with products for controlling parasites or phytopathogenic fungi or batteries1. In addition, miscibility is also interesting with solutions of mineral salts that are used to alleviate nutritional deficiencies and microelements. You can also add oils and non-phytotoxic oil concentrates.

Examples of obtaining Example 1 3- [7-Fluoro-4-hydroxy-4H-2,3-dihydro-benzoxa-cin-3-on-6-yl] -1-methyl-6-trifluoromethyl-1, 2, 3, 4- tetrahydropy-rimidin-2,4-dione (compound 1.01) A suspension from 3- [4-butoxycarbonylmethoxy-2-fluoro-5-nitro-phenyl] -l-methyl-6-trifluoromethyl-1,2,4,4-tetrahydropy-rimidin-2,4-dione (23 g), palladium on charcoal (5%, 1 g) in 200 ml of N-methylmorpholine is hydrogenated at 25 to 20 ° C with 0.1 bar of hydrogen overpressure. After absorption of 2.14 1 of hydrogen, the solvent is removed at 50 to 55 ° C in the vacuum of the oil pump. The residue is taken up in 200 ml of dichloromethane, after which the solution is washed three times with water and then dried over sodium hydrogen sulphate. Yield: 20 g.

EXAMPLE 2 3- [7-Fluoro-4-propargyloxy-4H-2,3-dihydro-benzoxa-cin-3-on-6-yl] -l-methyl-6-trifluoromethyl-1,2,3-tetrahydropi -rimidine-2,4-dione (compound 1.05) To a solution of 3- [7-fluoro-4-hydroxy-4H-2, 3-dihydro-benzo-xacin-3-on-6-yl] -1-methyl-6-trifluoromethyl-1, 2,3,4-tetrahydro-pyrimidine-2,4-dione (1.9 g) in 100 ml of N, N-dimethylformamide are added potassium carbonate (0.76 g) and 3-bromopropine * (0, 41 ml). After having stirred for 5 hours at approx. 20 ° C the solvent is removed, the residue is taken up in 150 ml of dichloromethane and washed three times with 30 ml of water each time. The organic phase is dried over sodium sulfate and freed from the solvent. After chromatography on silica gel (eluent: di-chloromethane / ethyl acetate 9: 1), 0.5 g of the useful product are obtained.

Example 3 3- [4-amino-7-fluoro-4H ~ 2, 3-dihydro-benzoxacin-3-on-6-yl] -1-methyl-6-trifluoromethyl-1, 2,3, 4- tetrahydropyrimidin-2,4-dione (compound 1.03) To a solution of 3- [7-fluoro-4H-2,3-dihydro-benzoxa-cin-3-on-6-yl] -l-methyl-6-trifluoromethyl-1, 2, 3, 4-tetrahydropy rimidin-2, 4-dione (3.6 g) in 50 ml of acetic ester are added potassium carbonate (2.8 g) and 2,4-dinitrofenoxiamine (2.2 g). Next, the reaction mixture is stirred for 10 hours at 45 to 50 ° C. After cooling, the proportion of solid formed is separated and the useful product, contained therein, is washed with diisopropylether. The diisopropyl ether phase is then combined with the reaction solution freed from the solids. The organic phase thus obtained is washed twice with each time 25 ml of water, dried over sodium sulfate and then concentrated.

Since according to the H-NMR spectrum the entire amount of the starting compound has not been transformed, it is again aminated using potassium carbonate (1.1 g) and 2,4-dinitrofenoxiamine (0.8 g). The further processing was carried out, for example, in the manner indicated above. Total yield: 1.2 g.

Example 4 3- [4-Acetoxy-7-fluoro-4H-2,3-dihydro-benzoxacin-3-on-6-yl] -l-methyl-6-trifluoromethyl-1,2,3,4-tetrahydropyrim -din-2, 4-dione (comp. 1.07) To a solution of 3- [7-fluoro-4-hydroxy-4H-2, 3-dihydro-benzo-xacin-3-on-6-yl] -1-methyl-6-trifluoromethyl-1, 2, 3, 4-Tetrahydro-pyrimidine-2,4-dione (1.9 g) in 100 ml of N, N-dimethylformamide are added potassium carbonate (0.76 g) and acetyl chloride (0.39 ml) After stirring for 5 hours at room temperature, the solvent is removed The residue is taken up in 150 ml of dichloromethane The organic phase is washed three times with 30 ml of water each time, then dried Sodium sulfate is added and concentrated, after chromatography on silica gel (eluant: dichloromethane / ethyl acetate 9: 1) 0.5 g useful product is obtained.

In the following Table 2, in addition to the above-mentioned compounds, other 3-aryluracils I are indicated which can be obtained analogously: Table 2 Application examples (herbicidal activity) The herbicidal activity of the 3-aryluracils I can be illustrated by the following tests carried out in the greenhouse: Plastic pots with clayey sand with ca. 3.0% humus as substrate. The seeds of the test plants were seeded separately according to the species.

In the treatment before the emergency, active substances suspended or emulsified in water were applied directly after sowing by means of fine distribution nozzles. The containers were irrigated slightly in order to promote germination and growth, and were then covered with plastic bags until the plants had taken root. This coating produces a uniform germination of the test plants, insofar as this was not counteracted by the active substances.

For the post-emergence treatment the test plants were allowed to grow, depending on their growth pattern up to a growth height of 3 to 15 cm and then treated with the suspended or emulsified active substances. The test plants were seeded directly in the same containers, in which they were grown, or were first grown separately as seedlings and not planted in the test vessels, but shortly before the treatment. In the postemergence treatment the active substances were applied in an amount of 0.0078 to 0.0039 kg / ha of s.a. (active substance) .

The plants were maintained according to their species at temperatures of 10-25 ° C or 20-35 ° C. The trial period lasted 2 to 4 weeks. During this time, the plants were taken care of and their reaction to the different treatments was evaluated.

The evaluation was based on a graduated scale of 0 to 100, where 100 means no emergence or total destruction of the plants, at least of the parts at ground level, and 0 means no damage or normal evolution of growth.

The plants used in the greenhouse trials include the following species: Given an application amount of 0.0078 or 0.0039 kg / ha of s.a., compound No. 1.08 gave a very good activity against the plants indicated above in post-mergency treatments.

Application examples (desiccant / defoliant action) As test plants, young cotton plants with 4 leaves (without germinal leaves) were used, which were grown under greenhouse conditions (relative humidity of the air 50 to 70%, diurnal / night temperature 27/20 ° C).

The leaves of the young cotton plants were treated until they dripped with aqueous preparations of the active substances indicated (with addition of 0.15% by weight of the fatty alcohol alkoxylate Plurafac LF 700, with respect to the spray liquid). The amount of water applied amounted to 1000 l / ha. After 13 days the number of warm leaves and the degree of defoliation were determined in percent. In the control plants there was no leaf fall.

Claims (1)

1. Claims 3-Aryluracils of the general formula I in which the variables have the following meanings: A hydrogen, methyl or amino; Ri hydrogen or halogen; R 2 is hydrogen, halogen, Ci-Cd-alkyl, Ci-Cβ-haloalkyl, Ci-Cß-alkylthio, Ci-Cβ-alkylsulfenyl or C?-C6-alkylsulfonyl; R3 hydrogen, halogen or Ci-Cβ-alkyl; X oxygen or -N (R7) -, meaning R7 hydrogen, Ci-Cß-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, (Ci-Cß-alkyl) carbonyl or Ci-Cß-alkoxy-Ci-Cß -I rent; ? i,? 2 each independently of the other, oxygen or sulfur; Z oxygen or -N (R8) -; R5, R6, R7, R8 each independently of the other, hydrogen, Ci-Cβ-alkyl, C-C6-alkenyl, C-Cg-alkynyl or Ci-Cβ-alkoxy-Ci-Cß-alkyl 2 or R5 represents together with R8 a second chemical bond; R4 hydrogen, C? -C6-alkyl, C3-C8-cycloalkyl, Ci-Cd-haloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, (C? -C6-alkyl) carbonyl, (C3-C6 -alkenyl) carbonyl, (C3-C6-alkynyl) carbonyl or Ci-Ce-alkylsulfonyl, each of the last 9 mentioned radicals being able to carry, if desired, one to three substituents selected from the following group comprising: halogen, nitro, cyano, hydroxy, C3-Cβ-cycloalkyl, Ci-Cβ-alkoxy, C3-Cβ-cycloalkoxy, C3-C6-alkenyloxy, C-C6-alkynyloxy, Ci-Ce-alkoxy- Ci- Cß-alkoxy, C?-C6-alkylthio, Ci-Cß-alkylsulphenyl, C?-C6-alkylsulfonyl, Ci-Cß-alkylidenaminooxi, the phenyl, phenoxy or phenylsulfonyl group, which may be unsubstituted or carry from one to three of the following radicals selected from the group consisting of: halogen, nitro, cyano, C? -C6-alkyl, Ci-C? -alkoxy and Cx-Cg-haloalkyl, a heterocyclyl, heterocyclyloxy, heterocyclylcarbonyl or heterocyclylcarbonyloxy group of 3 to 7 members and containing one to three heteroatoms as ring members, selected from a group comprising two oxygen atoms, two sulfur atoms and 3 nitrogen atoms, whose The heterocycle may be saturated, partially or completely unsaturated or aromatic and may, if desired, carry one to three substituents selected from the group comprising halogen, nitro, cyano, Ci-Ce-alkyl, Ci-Cβ-alkoxy, Ci-Cβ -halogen-noalkyl and (Ci-C-alkyl) carbonyl, a group -CO-R 9, -O-CO-R 9, -CO-OR 9, -O-CO-OR 9, -CO-SR 9, -O-CO-SR 9, -CO-N (R 9) R 1, -O -CO-NÍR9) Rl °, -N (R9) Ri ° or -C (NRH) -ORi2, meaning R9 hydrogen, Ci-Ce-alkyl, C3-Cβ-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, C? -C6-alkoxy-C? -C6-alkyl, (Ci-C6-alkoxy) carbonyl-C? -C6-alkyl, phenyl or phenyl-Ci-Ce-alkyl, which phenyl radicals can be unsubstituted or carry one to three radicals selected in each case from the group comprising halogen, nitro, cyano, Ci-C? -alkyl, Ci-Cβ-alkoxy and Ci-Cβ-haloalkyl, R10 hydrogen, hydroxy, C? -C6-alkyl, C3-C? -cycloalkyl, Ci-C? -alkoxy, C3-C6-alkenyloxy or (C? -C6-alkoxy) carbonyl-Ci-C? -alkoxy, R11 Ci-Cg-alkoxy, C3-C6-alkenyloxy or (Ci-Cβ-alkoxyJ-carbonyl-Ci-Cß-alkoxy) Ri2 Ci-Cß-alkyl, C3-C6-alkenyl or (C? -C6-alkoxy) carbonyl-Ci-Cß-alkyl, as well as the salts useful for agriculture of those compounds, in which A means hydrogen * 3-Aryluracils of the formula I according to claim 1 wherein the variables have the following meanings: A amino or methyl; R1 hydrogen, fluoro or chloro; R2 halogen, C6C6alkyl, Ci-C4-haloalkyl or Ci-Cβ-alkylsulfonyl; R3 hydrogen or halogen; X oxygen or -N (R7) -, meaning R7 hydrogen or Ct-Cβ-alkyl; ? i, Y2 oxygen; z oxygen or -N (R8) -; R5, R6, R8 each independently of the other, hydrogen or C? -C6-alkyl; or R6 and R8 together form a second chemical bond; R4 hydrogen, Ci-Cβ-alkyl, C3-Cβ-cycloalkyl, Ci-Cd-halogenoalkyl, C3-C6-alkenyl, C3-C6-alkynyl, (Ci-C-alkyl) carbonyl, (C3-C6-alkenyl carbonyl, (C3-C6-alkynyl) carbonyl or Ci-Ce-alkylsulphonyl, each of the last 9 radicals mentioned being able to carry, if desired, one or two substituents, each selected from the group comprising halogen, nitro, cyano, hydroxy, C3-Cß-cycloalkyl, C?-C6-alkoxy, C3-Cß-cycloalkoxy, C3-C6 ~ alkenyloxy, C3-C6-alkynyloxy, Ci-Cß-alkoxy- -Ce-alkoxy, Ci-C's-a? -thylthio, Ci-C-alkylsulphenyl, Ci-Cd-alkylsulfonyl, Ci-C-alkyldidenaminooxi, a heterocyclyl, heterocyclyloxy, heterocyclylcarbonyl or heterocyclylcarbonyloxy group of 3 to 7 members and with one to three heteroatoms as ring members, selected from the group comprising two oxygen atoms, two atoms 10 of sulfur and 3 nitrogen atoms, the heterocycles of which may be saturated or partially or totally unsaturated or aromatic and, if desired, carry one to three substituents selected from the group consisting of halogen, nitro, cyano , Ci-Cβ-alkyl, Ci-Cβ-alkoxy, Ci-Cβ-halogenoalkyl and (Ci-Cß-alkyl) carbonyl, a group -C0-R9, -O-CO-R9, -CO-OR9, -O-CO-OR9, twenty - . 20 -CO-SR 9, -O-CO-SR 9, -CO-N (R 9) R 1, -0-CO-N (R 9) R 1, -N (R 9) R 10 or -C (NRH) -OR 2, where R9 means hydrogen, Ci-Ce-alkyl, C3-Cß-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, Ci-Cß-alkoxy-Ci-Cß-alkyl or (C?-C6-alkoxy) ) carbonyl-C? -C6-alkyl, Rio means hydrogen, hydroxy, C? -C6-alkyl, C-C-cycloalkyl or Ci-C? -alkoxy, Rii means C? -C6-alkoxy or C3-C6-alkenyloxy R2 means (C? -C6-alkoxy) carbonyl-C? -C6-alkyl. 3-Aryluracils of the formula I according to claim 1, wherein X means oxygen. 3-Aryluracils of the formula I according to claim 1, wherein X means -N (R7) -. 3-Aryluracils of the formula I according to claim 1, wherein Z means oxygen. 3-Aryluracils of the formula I according to claim 1, wherein Z means -N (R 8) -. 3-Aryluracils of the formula I according to claim 1, wherein Z means -N (R 8) - and R 8 together with R 6 mean a second chemical bond. 3-Aryluracils of the formula I according to claim 1, wherein Y 1 signifies oxygen. 3-Aryluracils of the formula I according to claim 1, wherein R 2 represents trifluoromethyl, chlorodifluoromethyl or pentafluoroethyl. Enamin esters of formula IV wherein Ll means Ci-Cβ-alkyl or phenyl and the variables Y2, A, R up to R6, Z and X have the meanings indicated in claim 1. Enamine carboxylates of the formula V wherein Li means Ci-Cβ-alkyl or phenyl and the variables Y2, A, R1 through R6, Z and X have the meanings indicated in claim 1. Use of the 3-aryluracils of the formula I and their salts useful for agriculture according to claim 1 as herbicides or for the desiccation / defoliation of plants. A herbicidal product containing a herbicidal active amount of at least one 3-aryluracil of the formula I or an I salt useful for agriculture, according to claim 1, and at least one liquid or solid inert support, as well as, in case of want it, at least one tensoactive substance. 14. Product for the desiccation and / or defoliation of plants containing a desiccant and / or defoliant active amount of at least one 3-aryluracil of the formula I or an I salt useful for agriculture, according to claim 1, and at least one liquid or solid inert support, as well as, if desired, at least one surfactant substance. 15. Process for obtaining products with herbicidal action, characterized in that a herbicidal active amount of at least one 3-aryluracil of the formula I or of a salt of I useful for agriculture, according to claim 1, and at least one support is mixed liquid or solid inert, and, if desired, at least one surfactant substance. 16. Process for obtaining desiccant and / or desfoliating action products, characterized in that a herbicidal active amount of at least one 3-aryluracil of the formula I or of a salt of I useful for agriculture is mixed according to claim 1, and at least one inert liquid or solid support, as well as, if desired, at least one surfactant. 17. Process for combating the growth of unwanted plants, characterized in that an active herbicidal amount of a 3-aryluracil of the formula I or an I salt useful for agriculture is made to act on the plants, its living space or seeds, according to the claim 1. 18. Process for desiccation and / or defoliation of plants, characterized in that a desiccant and / or defoliant active amount of a 3-arylacilyl of formula I or an I salt useful for agriculture is made to act on the plants, according to the invention. claim 1 19. Process for the preparation of 3-aryluracils of the formula 1 according to claim 1, characterized in that either a) an enamin ester of formula IV is cyclized or an enamine carboxylate of the formula V b) a 3-aryuracil of the formula I is methylated or amine, where A means hydrogen; c) a 3-aryluracil of the formula I is treated, where Y 1 signifies oxygen, with a sulfiding agent; d) a 3-aryluracil of the formula I is halogen, where R3 signifies hydrogen; e) a 3-aryluracil of the formula I is alkylated or acylated, where R 4 signifies; f) a hocyclic compound of the formula VI is aminated in the presence of a base, or g) a nitrocompound of the formula VII is reduced where L2 means low molecular weight alkyl, in a hydroxylamine VIII and then cyclize VIII. 20. Hydroxylamines of the formula VIII wherein L2 means low molecular weight alkyl and the variables A, R, R2, R3, Y1, Z, R5 and R6 have the meanings indicated in claim 1. 21. Phenyl urea derivatives of the formula X where A, R1, X, Y2, Z, R4, R5 and R6 have the meanings indicated in claim 1. Phenyl isocyanates of the formula XII where R1, X, Y2, Z, R4, R5 and R6 have the meanings indicated in claim 1. SUMMARY OF THE INVENTION 3-Aryluracils and their salts (with A = hydrogen) where A = H, CH 3, NH 2; Ri = hydrogen or halogen; R2 = H, halogen, C? -C6-alkyl, C? -C6-haloalkyl, C? -C6-alkylthio, Cx-C? -alkylsulfenyl or C? -C6-alkylsulfonyl; R3-H, halogen or C? -C6 alkyl; X = oxygen or -N (R7) -, with R7 = C? -C6-alkyl, C3-Cs-alkenyl, C3-C6-alkynyl, C? -C6-alky) caxbonyl or C? -C6-alkoxy -C? -C6-alkyl; ? i, Y2 = oxygen or sulfur; Z = oxygen or -N (R8) -; Rrj, R6, R7, R8 = H, C? -C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl or C? -C6-alkoxy-C? -C6-alkyl; or R6 together with R8 represents a second chemical bond; R4 = H, C? -C6-alkyl, C3-C? -cycloalkyl, C? -C6-haloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, C? -C6-alkylcarbonyl, C3-C6 -alkenylcarbonyl, C3-C6-alkyne) carbonyl or C? -C.sub.-alkylsulfonyl, each of the last 9 radicals mentioned being capable of carrying 1-3 substituents: halogen, nitro, cyano, hydroxy, C-C? -cycloalkyl, C? C6-alkoxy, C3-Cß-cycloalkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C?-C6-alkoxy-C?-CG-alkoxy, C?-C6-alkylthio, C?-Cs- alkylsulfenyl, C6-alkylsulfonyl, C6-alkylidenaminoxy, phenyl, phenoxy or phenylsulfonyl, optionally substituted, a hocyclyl, hocyclyloxy, hocyclylcarbonyl or hocyclylcarbonyloxy group of 3 to 7 members with 1-3 hoatoms , -CO-R 9, -O-CO-R 9, -CO-OR 9, -O-CO-OR 9, -CO-SR 9, -0-CO-SR 9, -CO-N (R 9) R 1, -O-C 0 -N (R9) Rl °, -N. { R9) Rl ° O -C (NRll) -0Rl2 R9 = H, C? -C6-alkyl, C3-C? -cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, C? -C6-C-C6-alkoxy-alkyl, (C? -C6-al coxy) carbonyl-C? -C6-alkyl, phenyl event. sust or phenyl-C? -C6-alkyl; Ri ° = H, OH, C? -C6-alkyl, C3-C8-cycloalkyl, C? -C6-alkoxy, C3-C6-alkenyloxy, C? -C6-alkoxy) carboni-C? -C6-alkoxy, Ri i = C? -C6-alkoxy, C3-C6-alkenyloxy, C? -C6-alkoxycarbonyl-C? -C6-alkoxy Ri2 = C? -C6-alkyl, C3-C6-alkenyl, C? -C6-alkoxycarbonyl - C? -C6-alkyl. Use: as herbicides; for the desiccation / defoliation of plants