 Benzylhydroxylamine and Intermediates Used to Prepare the Same
专利摘要:
The present invention relates to benzylhydroxylamine of formula (I). The present invention also relates to salts of formula (I) wherein R 3 , R 7 and / or R 8 are hydrogen. These compounds are useful as herbicides and for drying and / or dead leaves of plants. <Formula I> Where X is -N (R 7 ) -O-; Y is O or S, R 1 is halogen, CN, NO 2 or CF 3 , R 2 is H or halogen, R 3 is H, NH 2 or CH 3 , R 4 is H, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkyl halide, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulfinyl or C 1 -C 6 -alkyl Sulfonyl, R 5 is H, halogen or C 1 -C 6 -alkyl, R 6 is H, C 1 -C 6 -alkyl, C 1 -C 6 -alkyl halide, C 3 -C 6 -cycloalkyl or C 2 -C 6 -alkenyl, R 8 is H, C 1 -C 6 -alkyl, C 3 -C 8 -cycloalkyl, C 1 -C 6 -alkyl halide, C 3 -C 6 -alkenyl or C 3 -C 6 -alkynyl, Each of the last five radicals may carry 1 to 3 substituents. 公开号:KR19990028722A 申请号:KR1019980700020 申请日:1996-06-27 公开日:1999-04-15 发明作者:랄프 크린츠；게르하르트 함프레흐트；엘리자베트 하이스트라허；페터 쉐퍼；치릴 자가르；카를-오토 베스트팔렌；헬무트 발터；울프 미쓸리츠；올라프 멘케；마르쿠스 멘게스 申请人:스타르크, 카르크；바스프 악티엔게젤샤프트； IPC主号:
专利说明:
Benzylhydroxylamine and Intermediates Used to Prepare the Same The present invention relates to novel benzylhydroxylamines of the general formula (I) in which the substituents have the following meanings and to agriculturally useful salts of these compounds (I) wherein R 3 , R 7 and / or R 8 are hydrogen. Where X is —N (R 7 ) —O—, which may be bonded to R 8 through oxygen or nitrogen, Y is oxygen or sulfur, R 1 is halogen, cyano or trifluoromethyl, R 2 is hydrogen or halogen, R 3 is hydrogen, amino or methyl, R 4 is hydrogen, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulfinyl or C 1 -C 6 -alkyl Sulfonyl, R 5 is hydrogen, halogen or C 1 -C 6 -alkyl, R 6 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl or C 2 -C 6 -alkenyl, R 7 is hydrogen, C 1 -C 6 -alkyl, C 3 -C 8 -cycloalkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, ( C 1 -C 6 -alkyl) carbonyl, (C 3 -C 6 -alkenyl) carbonyl, (C 3 -C 6 -alkynyl) carbonyl, (C 1 -C 6 -alkoxy) carbonyl, ( C 2 -C 6 -alkenyloxy) carbonyl, (C 2 -C 6 -alkynyloxy) carbonyl, (C 1 -C 6 -alkylthio) carbonyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -alkylcarbamoyl, each of the last 14 radicals mentioned Nitro, cyano, halogen, C 3 -C 8 -cycloalkyl, hydroxyl, C 1 -C 6 -alkoxy, C 3 -C 8 -cycloalkoxy, C 3 -C 6 -alkenyloxy, C 3- C 6 -alkynyloxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, (C 1 -C 6 -alkyl) carbonyl, (C 1 -C 6 -alkyl) carbonyloxy, C 1 -C 6 - alkylsulfinyl, C 1 -C 6 - alkylsulfonyl, C 1 -C 6 - alkylidene aminoxy when, C 1 -C 6 - alkyl-carbamoyl 1 to 3 substituents unsubstituted or selected from the group consisting of halogen, nitro, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy and C 1 -C 6 -haloalkyl A phenyl, phenoxy or phenylsulfonyl group, to which can be bonded, The heterocycle may be saturated, partially or fully unsaturated, aromatic, if necessary halogen, nitro, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6- From the group consisting of two oxygen atoms, two sulfur atoms and three nitrogen atoms to which one to three substituents selected from the group consisting of haloalkyl and (C 1 -C 6 -alkyl) carbonyl can be bonded 3- to 7-membered heterocyclyl or heterocyclyloxy group having 1 to 3 heteroatoms selected, -CO-Z 1 R 9 , -OCO-Z 1 R 9 or -N (R 9 ) R 10 groups 1 to 3 substituents selected from the group consisting of R 7 is C 3 -C 8 -cycloalkylcarbonyl, phenylcarbonyl, phenylsulfonyl or phenylcarbamoyl, wherein these four radicals are unsubstituted or halogen, nitro, cyano, C 1 -C 6- 1 to 3 substituents selected from the group consisting of alkyl, C 1 -C 6 -alkoxy and C 1 -C 6 -haloalkyl may be bonded, R 8 is hydrogen, C 1 -C 6 -alkyl, C 3 -C 8 -cycloalkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -alkenyl or C 3 -C 6 -alkynyl, Each of the last five radicals mentioned Nitro, cyano, halogen, C 3 -C 8 -cycloalkyl, hydroxyl, C 1 -C 6 -alkoxy, C 3 -C 8 -cycloalkoxy, C 3 -C 6 -alkenyloxy, C 3- C 6 -alkynyloxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsul Ponyl, C 1 -C 6 -alkylideneamioxy, 1 to 3 substituents unsubstituted or selected from the group consisting of nitro, cyano, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy and C 1 -C 6 -haloalkyl A phenyl, phenoxy or phenylsulfonyl group, to which can be bonded, The heterocycle may be saturated, partially or fully unsaturated or aromatic, if necessary halogen, nitro, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -halo Selected from the group consisting of two oxygen atoms, two sulfur atoms and three nitrogen atoms to which one to three substituents selected from the group consisting of alkyl and (C 1 -C 6 -alkyl) carbonyl can be bonded 3- to 7-membered heterocyclyl or heterocyclyloxy group having 1 to 3 heteroatoms, -CO-Z 2 -R 11 , -OCO-Z 2 -R 11 or -N (R 11 ) R 12 groups One to three substituents selected from the group consisting of may be bonded, Z 1 is a chemical bond, oxygen, sulfur or -N (R 10 )-, Z 2 is a chemical bond, oxygen, sulfur or -N (R 12 )-, R 9 , R 11 are independently of each other hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 8 -cycloalkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, (C 1 -C 6 -alkoxy) carbonyl-C 1 -C 6 -alkyl, phenyl or phenyl-C 1 -C 6 As alkyl, the phenyl ring of the phenyl group and the phenylalkyl group is unsubstituted, nitro, cyano, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy or (C 1 1 to 3 substituents selected from the group consisting of -C 6 -alkyl) carbonyl may be bonded, or In each case Z 1 and R 9 and / or Z 2 and R 11 are bonded together through nitrogen and one to three hetero atoms selected from the group consisting of two oxygen atoms, two sulfur atoms and three nitrogen atoms Is a 3- to 7-membered heterocycle having a heterocycle, which may be saturated, partially or fully unsaturated, or aromatic, if necessary, nitro, cyano, halogen, C 1 -C 6 -alkyl, C 1 -C 1 to 3 substituents selected from the group consisting of 6 -haloalkyl, C 1 -C 6 -alkoxy may be bonded, R 10 , R 12 are independently of each other hydrogen, hydroxyl, C 1 -C 6 -alkyl, C 3 -C 8 -cycloalkyl, C 1 -C 6 -alkoxy. Moreover, the present invention The use of compound I as a herbicide or for drying and / or dead leaves of plants, -Herbicidal compositions comprising compound I as active ingredient and a composition for drying and / or dead leaves of plants, -Use of compound I to control unwanted plants and to dry plants and / or dead leaves, -A method for producing the herbicidal composition and the composition for drying and / or defoliation of plants using Compound I and -A novel intermediate of formulas IV, V, XIII, XVI, XVII, XIX XXIII from which compound I can be obtained. International Publication No. 93/06090 and European Patent Publication No. 408 382 describe certain 3-phenyluracils as herbicides and for drying and / or defoliation of plants. It is different from compound I of the present invention in that an iminomethyl group is bonded instead of R 6 ) -XR 8 . According to International Patent Publication No. 95/06641, other compounds which are also suitable as herbicides and for drying and / or defoliation of plants are compounds of the formula (II). Where R a is hydrogen, fluorine or chlorine R b is particularly a hydroxyliminomethyl or oxyiminomethyl group. Finally, German Patent Publication No. 42 37 920 discloses that certain 3-aryluracils, in particular compounds of formula III, are suitable for weed control. Where R c is hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 4 -alkenyl or C 3 -C 4 -alkynyl, R d and R e are hydrogen, C 1 -C 8 -alkyl, C 3 -C 7 -cycloalkyl or C 3 -C 7 -cycloalkyl-C 1 -C 4 -alkyl, R f is hydrogen, C 1 -C 5 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyl-C 1- C 4 -alkyl, C 1 -C 5 -haloalkyl, C 2 -C 5 -alkenyl, C 2 -C 5 -alkynyl, unsubstituted or substituted aryl or benzyl, or a keto, ester or thioester group , R 5 ' is hydrogen, halogen or C 1 -C 4 -alkyl. However, the herbicidal properties of known compounds are not always completely satisfactory. It is therefore an object of the present invention to provide novel, in particular herbicidally active compounds which can allow unwanted plants to be better targeted than ever possible. Another object is to provide novel compounds with dry / foliar action. Thus, the inventors have found that the above object is achieved by the benzylhydroxylamine of the formula (I) and its production action. Moreover, we have found herbicidal compositions comprising Compound I and having good herbicidal action. In addition, methods of preparing these compositions and methods of controlling unwanted plants using Compound I have been found. Furthermore, it has been found that compound I is also suitable for partially drying and defoliating plants, suitable plants being crop plants such as cotton, potatoes, rapeseeds, sunflowers, oil or wild beans, in particular cotton. In this regard, compositions for drying and / or defoliation of plants, methods for preparing these compositions, and methods for controlling the drying and / or defoliation of plants using Compound I have been found. Depending on its substituted form, the compounds of formula (I) may contain one or more chiral centers, in which case they are present as enantiomers or diastereomer mixtures. The present invention relates to pure enantiomers or diastereomers and also mixtures thereof. If R 3 , R 7 and / or R 8 are hydrogen, benzylhydroxylamine I may be present in the form of its agriculturally useful salt, and in general the nature of this salt is not critical. In general, suitable salts are salts of these bases which do not adversely affect herbicidal action as compared to free compound I. Particularly suitable base salts are alkali metal salts, preferably sodium and potassium salts, alkaline earth metal salts, preferably calcium and magnesium salts, transition metal salts, preferably zinc and iron salts, and 1 to 4 C 1 when ammonium ions are required. Ammonium salts to which -C 4 -alkyl or hydroxyl-C 1 -C 4 -alkyl substituents and / or phenyl or benzyl substituents may be bonded, preferably diisopropyl ammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzyl Ammonium, and trimethyl (2-hydroxylethyl) ammonium salts Also phosphonium salts, sulfonium salts such as tri (C 1 -C 4 -alkyl) sulfonium salts and sulfoxnium salts Preferably, tri (C 1 -C 4 -alkyl) sulfonium salt. Organic residues mentioned for substituents R 4 to R 12 or for radicals on the phenyl ring or heterocycle are collective terms for the respective enumeration of each member of the group. All carbon chains, ie all alkyl, haloalkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylcarbonyl, alkoxycarbonyl, alkenyl, alkenyloxy, alkenylcarbonyl, alkynyl, alkynyloxy , Alkynylcarbonyl and alkylideneaminooxy residues may be straight or branched chain. Unless otherwise indicated, the halogenated substituent is preferably one to five identical or different halogen atoms bonded. Halogen is meant in each case fluorine, chlorine, bromine or iodine. Another example of the meaning is as follows. C 1 -C 4 -alkyl and (C 1 -C 6 -alkyl) carbonyl, (C 1 -C 6 -alkyl) carbonyloxy, C 1 -C 6 -alkylcarbamoyl, C 1 -C 6 Alkyl moieties of -alkoxy-C 1 -C 6 -alkyl and (C 1 -C 6 -alkoxy) carbonyl-C 1 -C 6 -alkyl are methyl, ethyl, n-propyl, 1-methylethyl, n-butyl , 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 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-dimethylbutyl , 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1, 2,2-trimethylpropyl, 1-ethyl-1-methylpropyl or 1-ethyl-2-methylpropyl; C 1 -C 4 -haloalkyl is the above-mentioned C 1 -C 4 -alkyl radical, partially or wholly substituted with fluorine, chlorine, bromine and / or iodine, for example chloromethyl, dichloromethyl, trichloro Chloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, 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 -Difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3, 3-trichloropro , 2,2,3,3,3-pentafluoropropyl, heptafluoropropyl, 1- (fluoromethyl) -2-fluoroethyl, 1- (chloromethyl) -2-chloroethyl, 1- ( Bromomethyl) -2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl, nonafluorobutyl, 5-fluoropentyl, 5-chloropentyl, 5-bromopentyl, 5-iodopentyl, undecafluoropentyl, 6-fluorohexyl, 6-chlorohexyl 6-bromohexyl 6-iodohexyl or dodecafluorohexyl; Phenyl-C 1 -C 6 -alkyl, for example, 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-phenylbut-1-yl, 4-phenylbut-1-yl, 1-phenylbut-2- 1, 2-phenylbut-2-yl, 3-phenylbut-2-yl, 4-phenylbut-2-yl, 1- (phenylmethyl) eth-1-yl, 1- (phenylmethyl) -1- (Methyl) eth-1-yl or 1- (phenylmethyl) prop-1-yl, preferably benzyl, 2-phenylethyl or 2-phenyl-hex-6-yl; - C 3 -C 6 - alkenyl, and C 3 -C 6 - alkenyloxy, and - alkenyl moiety of the (C 3 -C 6 alkenyl) carbonyl is prop-1-en-1-yl, prop- -2-en-1-yl, 1-methylethenyl, n-buten-1-yl, n-buten-2-yl, n-buten-3-yl, 1-methylprop-1-ene-1 -Yl, 2-methylprop-1-en-1-yl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, n-pentene-1 -Yl, n-penten-2-yl, n-penten-3-yl, n-penten-4-yl, 1-methylbut-1-en-1-yl, 2-methylbut-1-ene-1 -Yl, 3-methylbut-1-en-1-yl, 1-methylbut-2-en-1-yl, 2-methylbut-2-en-1-yl, 3-methylbut-2-ene -1-yl, 1-methylbut-3-en-1-yl, 2-methylbut-3-en-1-yl, 3-methylbut-3-en-1-yl, 1,1-dimethylpro Ph-2-en-1-yl, 1,2-dimethylprop-1-en-1-yl, 1,2-dimethylprop-2-en-1-yl, 1-ethylprop-1- En-2-yl, 1-ethylprop-2-en-1-yl, n-hex-1-en-1-yl, n-hex-2-en-1-yl, n-hex-3- En-1-yl, n-hex-4-en-1-yl, n-hex-5-en-1-yl, 1-methylpent-1-en-1-yl, 2-methylpent-1- En-1-yl , 3-methylpent-1-en-1-yl, 4-methylpent-1-en-1-yl, 1-methylpent-2-en-1-yl, 2-methylpent-2-ene-1 -Yl, 3-methylpent-2-en-1-yl, 4-methylpent-2-en-1-yl, 1-methylpent-3-en-1-yl, 2-methylpent-3-ene -1-yl, 3-methylpent-3-en-1-yl, 4-methylpent-3-en-1-yl, 1-methylpent-4-en-1-yl, 2-methylpent-4 -En-1-yl, 3-methylpent-4-en-1-yl, 4-methylpent-4-en-1-yl, 1,1-dimethylbut-2-en-1-yl, 1, 1-dimethylbut-3-en-1-yl, 1,2-dimethylbut-1-en-1-yl, 1,2-dimethylbut-2-en-1-yl, 1,2-dimethylbut- 3-en-1-yl, 1,3-dimethylbut-1-en-1-yl, 1,3-dimethylbut-2-en-1-yl, 1,3-dimethylbut-3-ene-1 -Yl, 2,2-dimethylbut-3-en-1-yl, 2,3-dimethylbut-1-en-1-yl, 2,3-dimethylbut-2-en-1-yl, 2, 3-dimethylbut-3-en-1-yl, 3,3-dimethylbut-1-en-1-yl, 3,3-dimethylbut-2-en-1-yl, 1-ethylbut-1- En-1-yl, 1-ethylbut-2-en-1-yl, 1-ethylbut-3-en-1-yl, 2-ethylbut-1-en-1-yl, 2-ethylbut- 2-en-1-yl, 2- Ylbut-3-en-1-yl, 1,1,2-trimethylprop-2-en-1-yl, 1-ethyl-1-methylprop-2-en-1-yl, 1-ethyl -2-methylprop-1-en-1-yl or 1-ethyl-2-methylprop-2-en-1-yl; - C 3 -C 6 - alkynyl and C 3 -C 6 - alkynyloxy and (C 3 -C 6 - alkynyl) alkynyl moiety of the carbonyl is prop-1-in-1-yl, prop- -2-yn-1-yl, boot-1-yn-1-yl, boot-1-yn-3-yl, boot-1-yn-4-yl, boot-2-yn-1-yl, pent -1-yn-1-yl, n-pent-1-yn-3-yl, n-pent-1-yn-4-yl, n-pent-1-yn-5-yl, n-pent-2 -Yn-1-yl, n-pent-2-yn-4-yl, n-pent-2-yn-5-yl, 3-methylbut-1-yn-3-yl, 3-methylbut-1 -Yn-4-yl, n-hex-1-yn-1-yl, n-hex-1-yn-3-yl, n-hex-1-yn-4-yl, n-hex-1-yne -5-yl, n-hex-1-yn-6-yl, n-hex-2-yn-1-yl, n-hex-2-yn-4-yl, n-hex-2-yn-5 -Yl, n-hex-2-yn-6-yl, n-hex-3-yn-1-yl, n-hex-3-yn-2-yl, 3-methylpent-1-yn-1- 3-methylpent-1-yn-3-yl, 3-methylpent-1-yn-4-yl, 3-methylpent-1-yn-5-yl, 4-methylpent-1-yn- 1-yl, 4-methylpent-2-yn-4-yl or 4-methylpent-2-yn-5-yl; - C 2 -C 6 - alkenyl and (C 2 -C 6 - alkenyloxy) carbonyl of alkenyl residues are vinyl or C 3 -C 6 - alkenyl, referring to the one of a radical, The alkynyl moiety of (C 2 -C 6 -alkynyloxy) carbonyl is one of the radicals mentioned for ethynyl or C 3 -C 6 -alkynyl; C 1 -C 6 -alkoxy and C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, (C 1 -C 6 -alkoxy) carbonyl and (C 1 -C 6 -alkoxy) carbonyl-C Alkoxy moieties of 1- C 6 -alkyl are methoxy, ethoxy, n-propoxy, 1-methylethoxy, n-butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1-dimethyl Methoxy, n-pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1 Ethylpropoxy, n-hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2- Trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy or 1-ethyl-2-methylpropoxy; - C 1 -C 6 - alkylthio and (C 1 -C 6 - alkylthio) carbonyl moiety of the alkylthio are methylthio, ethylthio, n- propyl thio, 1-methyl ethylthio, n- butylthio, 1 -Methylpropylthio, 2-methylpropylthio, 1,1-dimethylethylthio, n-pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, n-hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio , 1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1 -Ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio or 1-ethyl-2-methylpropylthio ego; C 1 -C 6 -alkylsulfinyl is methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, 1-methylethylsulfinyl, n-butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsul Finyl, 1,1-dimethylethylsulfinyl, n-pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, 2,2-dimethylpropylsulfinyl, 1-ethyl Propylsulfinyl, 1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, n-hexylsulfinyl, 1-methylpentylsulfinyl, 2-methylpentylsulfinyl, 3-methylpentylsulfinyl, 4 -Methylpentylsulfinyl, 1,1-dimethylbutylsulfinyl, 1,2-dimethylbutylsulfinyl, 1,3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl , 3,3-dimethylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl, 1,1,2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl, 1-ethyl- 1-methylpropylsulfinyl or 1-ethyl-2-methylpropylsulfinyl; C 1 -C 6 -alkylsulfonyl is methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, 1-methylethylsulfonyl, n-butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsul Ponyl, 1,1-dimethylethylsulfonyl, n-pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethyl Propylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, n-hexylsulfonyl, 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-ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl, 1-ethyl- 1-methylpropylsulfonyl or 1-ethyl-2-methylpropylsulfonyl; C 1 -C 6 -alkylidene-aminooxy, acetylidene-aminooxy, 1-propylidene-aminooxy, 2-propylidene-aminooxy, 1-butylidene-aminooxy, 2-butylidene-amino Oxy or 2-hexylideneaminoxi; C 3 -C 6 -cycloalkyl is cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl; C 3 -C 8 -cycloalkyl is cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl; C 3 -C 8 -cycloalkoxy is cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cycloheptyloxy or cyclooctyloxy; Examples of 3-7 membered heterocycles are oxiranyl, aziridinyl, oxetanyl, tetrahydrofunyl, tetrahydrothienyl, pyrrolidinyl, isoxoxazolidinyl, isothiazolidinyl, pyrazolidinyl, oxazolidinyl Dioxolanyl, such as thiazolidinyl, imidazolidinyl, 1,3-dioxolan-2-yl and 1,3-dioxolan-4-yl, 1,3-dioxan-2-yl and 1,3 Dioxanyl, such as -dioxan-4-yl, dithianil, such as 1,3-dithia-2-yl, also 1,2,4-oxadiazolidinyl, 1,3,4-oxadiazolidinyl, 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-isoxazolinyl, 4.5-isoxazolinyl, 2,3-isothiazolinyl, 3,4-isothiazolinyl, 4,5-isothiazolinyl, 2,3-dihydropyrazolyl, 3,4- Hydropyrazolyl, 4,5-dihydropyrazolyl, 2,3-dihydrooxazolyl, 3,4-dihydrooxazolyl, piperidinyl, tetrahydropyridazinyl, tetrahydropyrimidinyl, tetrahydropyra Genyl, 1,3,5-tetrahydrotriazinyl and 1,2,4-tetrahydrotriazinyl, and The following heteroaromatic compounds: furyl, such as 2-furyl and 3-furyl, thienyl, such as 2-thienyl and 3-thienyl, pyrrolyl, 2-pyrrolyl and 3-pyrrolyl, 3-isoxazolyl, Isoxazolyl such as 4-isoxazolyl and 5-isoxazolyl, isothiazolyl such as 3-isothiazolyl, 4-isothiazolyl and 5-isothiazolyl, 3-pyrazolyl, 4-pyrazolyl and Pyrazolyl such as 5-pyrazolyl, oxazolyl such as 2-oxazolyl, 4-oxazolyl and 5-oxazolyl, thiazolyl such as 2-thiazolyl, 4-thiazolyl and 5-thiazolyl, 2-imi Imidazolyl, such as dazolyl and 4-imidazolyl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl and 1,3,4-oxadia Oxadiazolyl, such as zol-2-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl and 1,3,4-thiadiazol-2- Thiazolyl, such as thiadiazolyl, 1,2,4-triazol-1-yl, 1,2,4-triazol-3-yl, and 1,2,4-triazol-4-yl, 2- blood Pyridinyl such as divinyl, 3-pyridinyl and 4-pyridinyl, pyridazinyl such as 3-pyridazinyl and 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl and 5-pyrimidinyl Pyrimidinyl, such as 2-pyrazinyl, 1,3,5-triazin-2-yl and 1,2,4-triazin-3-yl, in particular pyridyl, pyrimidyl, furanyl and thienyl to be. All phenyl and heterocycle rings are preferably unsubstituted or bonded to halogen, methyl, trifluoromethyl or methoxy substituents. With regard to the use of the compounds of the general formula (I) according to the invention as herbicides and / or as compounds having a dead leaf / drying action, the variables preferably have the following meanings and in each case are used alone or in combination. X is —N (R 7 ) —O—, which is bonded to R 8 through oxygen, X is —ON (R 7 ) — which is bonded to R 8 through nitrogen, Y is oxygen, R 1 is halogen or cyano, R 2 is hydrogen, fluorine or chlorine, R 3 is amino or methyl, R 4 is C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl or C 1 -C 6 -alkylsulfonyl, particularly preferably C 1 -C 4 -haloalkyl, in particular trifluoromethyl, chloro Difluoromethyl or pentafluoroethyl, R 5 is hydrogen or halogen, R 6 is hydrogen or C 1 -C 4 -alkyl, particularly preferably hydrogen, R 7 is hydrogen, C 1 -C 6 -alkyl, C 3 -C 8 -cycloalkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, ( C 1 -C 6 -alkyl) carbonyl, (C 3 -C 6 -alkenyl) carbonyl, (C 3 -C 6 -alkynyl) carbonyl, (C 1 -C 6 -alkoxy) carbonyl, ( C 2 -C 6 -alkenyloxy) carbonyl, (C 2 -C 6 -alkynyloxy) carbonyl, (C 1 -C 6 -alkylthio) carbonyl, C 1 -C 6 -alkylcarbamoyl And each of the last 13 radicals Nitro, cyano, halogen, C 3 -C 8 -cycloalkyl, hydroxyl, C 1 -C 6 -alkoxy, C 3 -C 8 -cycloalkoxy, C 3 -C 6 -alkenyloxy, C 3- C 6 -alkynyloxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsul Ponyl, C 1 -C 6 -alkylideneamioxy, -CO-Z 1 R 9 , -OCO-Z 1 R 9 or -N (R 9 ) R 10 groups 1 to 2 substituents selected from the group consisting of may be bonded; R 8 is hydrogen, C 1 -C 6 -alkyl, C 3 -C 8 -cycloalkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -alkenyl or C 3 -C 6 -alkynyl, If necessary, each of the last five radicals mentioned Nitro, cyano, halogen, C 3 -C 8 -cycloalkyl, hydroxyl, C 1 -C 6 -alkoxy, C 3 -C 8 -cycloalkoxy, C 3 -C 6 -alkenyloxy, C 3- C 6 -alkynyloxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsul Ponyl, C 1 -C 6 -alkylideneamioxy, -CO-Z 2 R 11 , -OCO-Z 2 R 11 or -N (R 11 ) R 12 groups One to two substituents selected from the group consisting of may be bonded, Z 1 is a chemical bond, oxygen, sulfur or -N (R 10 )-, Z 2 is a chemical bond, oxygen, sulfur or -N (R 12 )-, R 9 , R 11 are independently of each other hydrogen, C 1 -C 6 -alkyl, C 3 -C 8 -cycloalkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl or (C 1 -C 6 -alkoxy) carbonyl-C 1 -C 6 -alkyl, or In each case Z 1 and R 9 and / or Z 2 and R 11 are bonded together through nitrogen and one to three hetero atoms selected from the group consisting of two oxygen atoms, two sulfur atoms and three nitrogen atoms 3- to 7-membered heterocycles with heterocycles, which may be saturated, partially or fully unsaturated, or aromatic, if necessary in each case nitro, cyano, halogen, C 1 -C 6 -alkyl , C 1 -C 6 - haloalkyl and C 1 -C 6 -, and the 1 to 3 substituents selected from the group consisting of alkoxy group can be coupled, R 10 , R 12 are independently of each other hydrogen or C 1 -C 6 -alkyl. R 7 is particularly preferably hydrogen, C 1 -C 6 -alkyl, C 3 -C 8 -cycloalkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -alkenyl, C 3 -C 6- Alkynyl, (C 1 -C 6 -alkyl) carbonyl, (C 3 -C 6 -alkenyl) carbonyl, (C 3 -C 6 -alkynyl) carbonyl, (C 1 -C 6 -alkoxy) Carbonyl or C 1 -C 6 -alkylcarbamoyl, each of the last 10 radicals being nitro, cyano, halogen, C 3 -C 8 -cycloalkyl, hydroxyl, C 1 -C 6 -alkoxy, C 3 -C 8 -cycloalkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 -alkynyloxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy, C 1 -C 6- alkylthio, C 1 -C 6 - alkylsulfonyl phenyl, C 1 -C 6 - alkylsulfonyl, C 1 -C 6 - alkylidene aminoxy City, CO-Z 1 R 9, -OCO-Z 1 R 9 or One of the —N (R 9 ) R 10 groups may be bonded. R 8 is particularly preferably hydrogen, C 1 -C 6 -alkyl, C 3 -C 8 -cycloalkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -alkenyl or C 3 -C 6- Alkynyl, each of the last five radicals mentioned is nitro, cyano, halogen, C 3 -C 8 -cycloalkyl, hydroxyl, C 1 -C 6 -alkoxy, C 3 -C 8 -cycloalkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 -alkynyloxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 1 -C 6- Alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -alkylideneaminooxy, CO-Z 2 R 11 , -OCO-Z 2 R 11 or -N (R 11 ) R 12 groups One of them may be combined. Compound Ia shown in Table 1 below (X = -NH-O-, Y = oxygen, R 1 = chlorine, R 2 = fluorine, R 3 = amino, R 4 = trifluoromethyl and R 5 , R 6 = hydrogen Phosphorus I) is very particularly preferred. Another very particularly preferred benzylhydroxylamine of formula (I) is the following compound. The following compounds Ib.01 to Ib.84 differ from the corresponding compounds Ia.01 to Ia.84 in that R 1 is cyano. The following compounds Ic.01 to Ic.84 differ from the corresponding compounds Ia.01 to Ia.84 in that R 2 is hydrogen. The following compounds Id.01 to Id.84 differ from the corresponding compounds Ia.01 to Ia.84 in that R 1 is cyano and R 2 is hydrogen. The following compounds Ie.01 to Ie.84 differ from the corresponding compounds Ia.01 to Ia.84 in that R 3 is methyl. The following compounds If.01 to If.84 differ from the corresponding compounds Ia.01 to Ia.84 in that R 1 is cyano and R 3 is methyl. The following compounds Ig.01 to Ig.84 differ from the corresponding compounds Ia.01 to Ia.84 in that R 2 is hydrogen and R 3 is methyl. The following compounds Ih.01 to Ih.84 differ from the corresponding compounds Ia.01 to Ia.84 in that R 1 is cyano, R 2 is hydrogen and R 3 is methyl. Very particular preference is also given to compounds Ii shown in Table 2 (Y = oxygen, R 1 = chlorine, R 2 = fluorine, R 3 = amino, R 4 = trifluoromethyl and R 5 , R 6 = hydrogen) Do. Another very particularly preferred benzylhydroxylamine of formula (I) is the following compound. The following compounds Ik.98 to Ik.243 differ from the corresponding compounds Ii.01 to Ii.243 in that R 1 is cyano. The following compounds Il.01 to Il.243 differ from the corresponding compounds Ii.01 to Ii.243 in that R 2 is hydrogen. The following compounds Im.01 to Im.243 differ from the corresponding compounds Ii.01 to Ii.243 in that R 1 is cyano and R 2 is hydrogen. The following compounds In.01 to In.243 differ from the corresponding compounds Ii.01 to Ii.243 in that R 3 is methyl. The following compounds Io.01 to Io.243 differ from the corresponding compounds Ii.01 to Ii.243 in that R 1 is cyano and R 3 is methyl. The following compounds Ip.01 to Ip.243 differ from the corresponding compounds Ii.01 to Ii.243 in that R 2 is hydrogen and R 3 is methyl. The following compounds Iq.01 to Iq.243 differ from the corresponding compounds Ii.01 to Ii.243 in that R 1 is cyano, R 2 is hydrogen and R 3 is methyl. Also very particularly preferred compounds Ir (I where Y = oxygen, R 1 = chlorine, R 3 = methyl, R 4 = trifluoromethyl and R 5 , R 6 = hydrogen) are the compounds shown in Table 3 below. Finally, very particularly preferred benzylhydroxylamine I is the following compound. The following compounds Is.01 to Is.46 differ from the corresponding compounds Ir.01 to Ir.46 in that R 1 is cyano. The following compounds It.01 to It.46 differ from the corresponding compounds Ir.01 to Ir.46 in that R 3 is amino. The following compounds Iu.01 to Iu.46 differ from the corresponding compounds Ir.01 to Ir.46 in that R 1 is cyano and R 3 is amino. Benzylhydroxylamine of formula (I) can be obtained in various ways, for example by one of the following methods. Method A) Cyclization of an Enamine Ester of Formula IV or an Enamine Carboxylate of Formula V in the Presence of a Base: L 1 is low molecular weight alkyl, preferably C 1 -C 4 -alkyl or phenyl. Usually, the cyclization is an inert solvent or aprotic diluent, for example aliphatic or cyclic ethers such as 1,2-dimethoxyethane, tetrahydrofuran and dioxane, aromatics such as benzene and toluene, or dimethylformamide and dimethyl It is carried out in a polar solvent such as sulfoxide. Also suitable are mixtures of polar solvents and hydrocarbons such as n-hexane. Depending on the starting compound, water may also be suitable as a diluent. Preferably suitable bases are alkali metal alcoholates, in particular sodium alcoholates, alkali metal hydroxides, in particular sodium and potassium hydroxides, alkali metal carbonates, in particular sodium carbonate and potassium carbonate, metal hydrides, in particular sodium hydride. When using sodium hydride as the base, it has proved advantageous to carry out the process in aliphatic or cyclic ethers, dimethylformamide or dimethyl sulfoxide. In general, 0.5 to 2 times the molar amount of base, based on the amount of compound IV or V, is sufficient to successfully carry out the reaction. In general, the reaction temperature is from (-78) ° C to the boiling point of the reaction mixture, in particular from (-60) ° C to 60 ° C. If R 3 in formula IV or V is hydrogen, the process product is obtained with a metal salt corresponding to the cation of the base used. The salts can be separated and purified in a manner known per se, or if necessary, converted to the free compound I in which R 3 = hydrogen by acid. Method B) Methylation of Compound I in which R 3 is hydrogen in the presence of a base: Examples of suitable methylating agents are methyl halides, preferably methyl chloride, methyl iodide or methyl bromide, and also dimethyl sulfate, methanesulfonate (methyl mesylate), methylbenzenesulfonate, methane-p-tolylsulfo Acetates (methyl tosylate), methane-p-bromobenzenesulfonate (methyl brosylate), methyl trifluoromethanesulfonate (methyltriplate) and diazomethane. Usually, the process is carried out in an inert organic solvent, for example a mixture with water if necessary, a proton solvent such as a lower alcohol, preferably ethanol, or an aprotic solvent, for example aliphatic or cyclic ethers, preferably 1,2 -Dimethoxyethane, tetrahydrofuran and dioxane, aliphatic ketones, preferably acetone, amide, preferably dimethylsulfonamide, sulfoxide, preferably dimethyl sulfoxide, tetramethylurea and 1,3-dimethyltetrahydro Urea, such as -2 (1H) -pyrimidinone, carboxylic acid esters such as ethyl acetate, or aromatic hydrocarbons such as dichloromethane and chlorobenzene. Suitable bases include inorganic bases such as carbonates such as sodium carbonate and potassium carbonate, hydrogen carbonates such as sodium bicarbonate and potassium hydrogen carbonate, or alkali metal hydrides such as sodium hydride and potassium hydride, and organic bases such as Amines such as triethylamine, pyridine and N, N-diethylaniline, or alkali metal alcoholates such as sodium methanolate, sodium ethanolate and potassium tert-butanolate. The amount of base and methylating agent is preferably in each case from 0.5 to 2 times the molar amount, based on the amount of starting compound. In general, the reaction temperature is from 0 ° C. up to the boiling point of the reaction mixture, in particular from 0 ° C. to 60 ° C. Preferred method parameters are compounds IV (R 3 = H) or V (R 3 = according to method A) without separation from the reaction mixture, which may still contain excess base such as sodium hydride, sodium alcoholate or sodium carbonate. And methylation of the salt of Compound I obtained by cyclization of H). If they cannot be prepared directly by the cyclization described in method A) under alkaline conditions, the salts of these compounds I in which R 3 is hydrogen can also be obtained in a manner known per se from the method product of method A). Eventually, for example, an aqueous solution of an inorganic or organic base is treated with benzylhydroxylamine I, in which R 3 is hydrogen. In general, the salts form rapidly and sufficiently at temperatures as high as 20-25 ° C. It is particularly advantageous to prepare salts by dissolving benzylhydroxylamine I (R 3 is hydrogen) in aqueous sodium hydroxide solution at 20-25 ° C. using approximately equal amounts of benzylhydroxylamine and sodium hydroxide. The salts of benzylhydroxylamine may then be separated, for example, by precipitation with a suitable inert solvent or by removing the solvent. In general, salts of benzylhydroxylamine I (R 3 is hydrogen) in which the metal ions of the salt are not alkali metal ions can be prepared by double decomposition of the corresponding alkali metal salt in an aqueous solution. Compounds that can be prepared in this manner are, for example, benzylhydroxylamine metal salts which are water insoluble. Method C) Reaction of benzylhydroxylamine of formula (I) wherein R 3 is hydrogen with an electrophilic amination agent in the presence of a base: Amination agents that have proven to be useful so far are 2,4-dinitrophenoxyamines, but as amination agents, for example, E. Hofer et al. Synthesis 1983, 466; W. Friedrichsen et al., Heterocycles 20 ( 1983) 1271; H. hart et al., Tetrahedron Lett. 25 (1984) 2073; B. Vercek et al., Monatsh. Chem. 114 (1983) 789; G. Sonsnousky et al., Z. Naturforsch. 38 ( (1983) 884; see also RS Atkinson et al., J. Chem. Soc. Perkin Trans. 1987, 2787). Hydroxylamine-O-sulfonic acid (HOSA) may also be used. Amination can be carried out in a manner known per se (for example, T. Sheradsky, Tetrahedron Lett. 1968, 1909, MP Wentland et al., J. Med. Chem. 27 (1984) 1103 and in particular, auras of uracil). See European Patent Publication Nos. 240 194, 476 697 and 517 181, which teach folk paintings) Typically, the reaction is carried out in a polar solvent, for example dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide or ethyl acetate, which has thus far been proved to be particularly suitable. Suitable bases are, for example, alkali metal carbonates such as potassium carbonate, alkali metal alcoholates such as sodium methanolate and potassium tert-butanolate or alkali metal hydrides such as sodium hydride. The amount of base and aminating agent is preferably in each case from 0.5 to 2 times the molar amount based on the starting compound. Depending on the meaning of R 7 and R 8 , it may be necessary to protect these substituents against amination in a manner known per se. It is especially recommended if R 7 and R 8 are hydrogen. Method D) Sulfation of Benzylhydroxylamine of Formula (I) wherein Y = Oxygen: Generally, sulfiding is carried out in an inert solvent or diluent, for example aromatic hydrocarbons such as toluene and xylene, ethers such as diethylether, 1,2-dimethoxyethane and tetrahydrofuran, or organic amines such as pyridine. In particular, phosphorus sulfide (V) and 2,4-bis (4-methoxyphenyl) -1,3,2,4-dithiadiphosphetane-2,4-dithion ("Lawesson reagent" ) Is particularly suitable as a sulfiding agent. In general, 1 to 5 times the molar amount, based on the starting compound to be sulfided, is sufficient to complete the reaction. The reaction temperature is usually 20 ° C to 200 ° C, preferably 40 ° C to the boiling point of the reaction mixture. Method E) Alkylation or acylation of benzylhydroxylamine of compound I in which R 7 is hydrogen in the presence of a base: Alkylation is, for example, halides, preferably chloride or bromide, sulfate, sulfonate, preferably methanesulfonate (mesylate), benzenesulfonate, p-toluenesulfonate (tosylate), p-bromo Benzenesulfonate (brosylate), trifluoromethanesulfonate (triplate), or diazo compounds of unsubstituted or substituted alkanes, cycloalkanes, haloalkanes, alkenes or alkynes. Suitable acylating agents are acid halides of substituted or unsubstituted alkanes, cycloalkanes, alkenes, alkynes, or phenylcarboxylic acids, especially acid chlorides, anhydrides or isocyanates and sulfonyl chlorides. Alternatively, the free acid or anhydride thereof is also suitable if the process is carried out in the presence of condensing agents such as carbonyldiimidazole and dicyclohexylcarbodiimide. In general, the process comprises an inert organic solvent, preferably an aprotic solvent, for example aliphatic or cyclic ethers such as 1,2-dimethoxyethane, tetrahydrofuran and dioxane, aliphatic ketones such as acetone, dimethylformamide Amides such as, sulfoxides such as dimethyl sulfoxide, ureas such as tetramethylurea and 1,3-dimethyltetrahydro-2 (1H) -pyrimidinone, carboxylic acid esters such as ethyl acetate, or dichloromethane and chlorobenzene In halogenated aliphatic or aromatic hydrocarbons such as; Suitable bases are inorganic bases, for example alkali metal carbonates such as sodium carbonate and potassium carbonate, alkali metal hydrogen carbonates such as sodium bicarbonate and potassium hydrogen carbonate, or alkali metal hydrides such as sodium hydride and potassium hydride, and also organic bases. Amines such as, for example, triethylamine, pyridine and N, N-diethylaniline, or alkali metal alcoholates such as sodium methanolate, sodium ethanolate and potassium tert-butanolate. The amount of base and alkylating agent is preferably from 0.5 to 2 times the molar amount based on the amount of starting compound wherein R 7 is hydrogen. In general, reaction temperatures of from 0 ° C. to the reaction mixture, in particular from 0 ° C. to 60 ° C., are recommended. In addition, problems associated with the regio selectivity that can occur in the case of starting compounds in which R 3 is hydrogen can be avoided in a manner known per se (using 2 equivalents of base, introduction of protecting groups, etc.). Method F): Reduction of Oxymino Compounds of Formula VII: Examples of suitable reducing agents include hydrides such as borane complexes, for example borane-dimethyl sulfide or borane-pyridine complexes, also silanes such as triethylsilane and diphenylmethylsilane, or hydrogen using catalysts such as platinum on charcoal. It is a molecule. If hydrogen is used, it is recommended to react under acidic conditions, for example in an organic or inorganic acid with a solvent. In general, the hydrogen pressure is from atmospheric pressure to excess atmospheric pressure of approximately 10 bar. In general, reduction is successful at -5 ° C to + 50 ° C. The amount of reducing agent is not critical. The process can be carried out in small amounts based on the amount of compound VII or in molar amounts up to approximately 15 times or less. Preferably, from 0.5 to 2 molar amounts of reducing agent based on oxymino compound VII is used. Method G) Cleavage of an alkylideneaminooxy compound of Formula VIII: Cleavage is conveniently carried out using Bronsted acid as a catalyst. Typically, 0.5 to 2 molar amounts of acid are sufficient based on the amount of compound VIII. Suitable examples of acids are organic acids such as acetic acid and inorganic acids such as sulfuric acid and hydrochloric acid. The reaction can be carried out directly in an acid or inert solvent such as toluene. Advantageously, cleavage is carried out in the presence of oximes such as hydroxylamine and methylhydroxylamine, in which case the oxime is used in an excess of approximately equimolar amounts or up to 20 times the molar amount based on the amount of compound VIII. In general, a reaction temperature of from 0 ° C. to the boiling point of the reaction mixture is recommended. In other words, the alkylideneaminooxy compound VIII can be obtained, for example, from benzyl derivative IX. Usually, the reaction is carried out in an inert solvent / diluent with the desired alkylideneaminohydroxy HO-N = C (R a , R b ). If compound IX is used as the benzyl halide (IXa), it is convenient to carry out the process in the presence of an organic base such as triethylamine or an inorganic base such as sodium carbonate and potassium carbonate. Conversely, if benzyl alcohol (IXb) is used as a starting material, a condensation aid such as carbodiimidazole is required. Examples of suitable solvents are aromatics such as toluene and xylene, esters such as ethyl acetate, ethers such as diethylether and tetrahydrofuran, halogenated aliphatic such as methylene chloride, or base solvents such as pyridine and dimethylformamide. Compounds IX and alkylideneaminohydroxides are conveniently used in approximately stoichiometric amounts, or in slightly excess amounts of up to about 10 mole percent of the other one or other reactants. In general, the reaction temperature is carried out at the boiling point of the reaction mixture from 0 ° C. Method H) Reduction of benzyl alcohol IXa with hydroxylamine HO-N (R) -R: The process is preferably carried out in the presence of a condensation aid, such as carbodiimidazole, usually in an amount of 0.5 to 2 times the molar amount based on the amount of compound IXa. Usually, the reaction is carried out in an inert solvent such as hydrocarbons such as toluene and xylene, esters such as ethyl acetate or ethers such as diethyl ether and tetrahydrofuran. Compounds IX and Xa are conveniently used in approximately stoichiometric amounts, or otherwise using a slight excess of approximately 19 mole percent of one species or other reactant. In general, a reaction temperature of from 0 ° C. to the boiling point of the reaction mixture is recommended. Method K) Halogenation of Benzylhydroxylamine of Formula (I) wherein R 5 is hydrogen: Generally, halogenation is carried out in an inert organic solvent or diluent. Suitable materials for chlorination and bromination are, for example, aliphatic carboxylic acids such as acetic acid or chlorinated aliphatic hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride. Low boiling aliphatic carboxylic acids, such as acetic acid, are particularly preferred for iodide. Particularly suitable reagents for chlorination and bromination are chlorine or bromine elements, or else preferably sulfuryl chloride and sulfuryl bromide at reaction temperatures of 0 ° C. to 60 ° C., in particular 10 ° C. to 30 ° C. If desired, chlorination and bromination can be carried out in the presence of an acid-binder, particularly preferred reagents are sodium acetate and tertiary amines such as triethylamine, dimethylaniline and pyridine. The iodine element is particularly preferred as the iodide agent, in which case the reaction temperature is approximately 0 ° C to 110 ° C, preferably 10 ° C to 30 ° C. Iodide is particularly advantageously carried out in the presence of an inorganic acid such as steam nitric acid. The amount of halogenating agent is not critical and is generally used in an equivalent molar amount of halogenating agent or in excess of approximately 200 mol% or less, based on the starting compound (R 5 = H). Excess iodine can be removed after the reaction, for example, by saturated aqueous sodium hydrogen sulfite solution. Method L) Alkylation of hydroxylamine or hydroxylsamic acid with a benzyl halide or benzyl alcohol derivative of formula (XI) in the presence of a base: L 2 is halogen or lower alkylsulfonate, lower haloalkylsulfonate or phenylsulfonate, which may be substituted. Usually, the process is carried out in an inert solvent, and a suitable solvent is in particular an aprotic solvent, for example aliphatic or cyclic ethers such as 1,2-dimethoxyethane, tetrahydrofuran and dioxane, preferably Aliphatic ketones such as acetone, preferably amides such as dimethylformamide, sulfoxides such as dimethyl sulfoxide, urea such as tetramethylurea and 1,3-dimethyltetrahydrotetrahydro-2 (H) -pyrimidinone, ethyl Carboxylic esters such as acetates or halogenated aliphatic or aromatic hydrocarbons such as dichloromethane and chlorobenzene. Suitable bases include inorganic bases, for example alkali metal carbonates, in particular carbonates such as sodium carbonate and potassium carbonate, alkali metal hydrogen carbonates, in particular hydrogen carbonates such as sodium bicarbonate and potassium hydrogen carbonate, or alkalis such as sodium hydride and potassium hydride Metal hydrides, also organic bases such as triethylamine, pyridine and amines such as N, N-diethylaniline or alkali metal alcoholates such as sodium methanolate, sodium ethanolate and potassium tert-butanolate. The amount of base and alkylating agent XI is typically in each case from 0.5 to 2 times the molar amount based on compound X. In general, the reaction is carried out at (-78 ° C) to the boiling point of the reaction mixture, in particular at (-60 ° C) to 60 ° C. Enamine esters of formula IV are novel. These can be manufactured by a method known per se, for example, by one of the following methods. M): The process is preferably carried out under absolutely anhydrous conditions in an inert solvent or diluent, particularly preferably in the presence of an acidic or alkaline catalyst. Suitable solvents or diluents are especially organic solvents which form an azeotrope with water, for example aromatics such as benzene, toluene and xylene, halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride and chlorobenzene, 1,2-dimethoxy Aliphatic or cyclic ethers such as ethane, tetrahydrofuran and dioxane, or cyclohexane, as well as methanol and ethanol and alcohols. Preferably suitable acidic catalysts are strong inorganic acids such as sulfuric acid and hydrochloric acid, phosphorus containing acids such as orthophosphoric acid and polyphosphoric acid, organic acids such as p-toluenesulfonic acid, and acidic cations such as "Amberlyst 15" (Fluka) It is an exchange. Suitable base catalysts are, for example, metal hydrides such as sodium hydride, particularly preferably metal alcoholates such as sodium methanolate and ethanolate. It is recommended that compounds XIII and β-ketoester XII are conveniently used in stoichiometric amounts, or in slightly excess amounts of up to approximately 10 mol% of one or the other reactants. Generally, 0.5 to 2 molar amounts of catalyst are sufficient, based on the amount of one of the starting compounds. In general, the reaction is carried out rapidly at 60 to 120 ° C., preferably at the boiling point of the reaction mixture to remove the water formed. N): L 3 is C 1 -C 4 -alkyl or phenyl. This reaction is carried out, for example, in an inert organic solvent which is miscible with water, for example aliphatic or cyclic ethers such as 1,2-dimethoxyethane, tetrahydrofuran and dioxane, or lower alcohols, in particular ethanol, and The temperature is generally 50 to 100 ° C., preferably the boiling point of the reaction mixture. However, the reaction can also be carried out in aromatic diluents such as benzene, toluene and xylene, in which case an acidic catalyst such as hydrochloric acid and p-toluenesulfonic acid, or an alkali metal alcohol such as sodium methanolate and ethanolate Addition of rates is recommended. In this method variable, the reaction temperature is also generally from 50 to 100 ° C, preferably from 60 to 80 ° C. For quantities, the information provided in method M) applies here. O): The reaction is conveniently carried out with absolutely anhydrous aprotic solvents or diluents, for example aliphatic or cyclic ethers such as diethyl ether, 1,2-dimethoxyethane, tetrahydrofuran and dioxane, n-hexane, benzene, toluene And aliphatic or aromatic hydrocarbons such as xylene, halogenated aliphatic or aromatic hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, 1,2-dichloromethane and chlorobenzene, such as dimethylformamide, hexamethylphosphor triamide and dimethyl sulfoxide In the presence of an aprotic polar solvent or a mixture thereof. If desired, the process can also be carried out with metal hydride bases such as sodium hydride and potassium hydride, alkali metal alcoholates or alkaline earth metal alcoholates such as sodium methanolate, sodium ethanolate and potassium t-butanolate, or triethylamine and pyridine. It can be carried out in the presence of an organic tertiary base, and the organic base can act simultaneously as a solvent. It is convenient to use a stoichiometric amount of starting compound or else in a slight excess of up to approximately 10 mole percent of one or other component. If the process is carried out without solvent in the presence of an organic base, it is recommended to use an excessively large amount of the organic base. In general, the reaction temperature is sufficient to be (-80) to 50 ° C, in particular (-60) to 30 ° C. In a particularly preferred embodiment, the resulting enamine ester IV is converted directly to the corresponding desired product I according to method A) using an excess of base. Any by-products (eg, C-alkylation products in the case of compounds where R 5 = hydrogen) can be removed by conventional separation methods such as crystallization and chromatography. P): L 4 is C 1 -C 4 -alkyl or phenyl. This reaction is conveniently carried out in aprotic polar solvents or diluents, for example dimethylformamide, 2-butanone, dimethylsulfoxide and acetonitrile, advantageously bases such as alkali metal alcoholates or alkaline earth metal alcoholates. , In particular in the presence of sodium alkanolates such as sodium methanolate, alkali metal carbonates or alkaline earth metal carbonates, especially sodium carbonate, or alkali metal hydrides such as lithium hydride and sodium hydride. Generally, 0.5 to 2 molar amounts of base are sufficient, based on the amount of compound XV or XVII. In general, the reaction temperature is generally from 80 ° C. to 180 ° C., preferably the boiling point of the reaction mixture. As for the proportion of starting compounds, the information provided in method M) applies here. In a particularly preferred embodiment, sodium alcoholate is used as the base and the alcohol formed during the reaction is continuously evaporated off. The enamine ester IV prepared in this way is cyclized from the reaction mixture without separation according to method A) to obtain the corresponding salts of benzylhydroxylamine I. Q): This reaction is conveniently carried out absolutely with anhydrous aprotic solvents or diluents, for example aliphatic or cyclic ethers such as diethyl ether, 1,2-dimethoxyethane, tetrahydrofuran and dioxane, n-hexane, benzene, Aliphatic or aromatic hydrocarbons such as toluene and xylene, halogenated aliphatic or aromatic hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, 1,2-dichloroethane and chlorobenzene, dimethylformamide, hexamethylphosphor triamide and dimethyl sulfoxide; In the presence of the same aprotic polar solvent, or mixtures thereof. If desired, the process can also be carried out with metal hydride bases such as sodium hydride and potassium hydride, alkali metal alcoholates or alkaline earth metal alcoholates such as sodium methanolate, sodium ethanolate and potassium t-butanolate, or triethylamine and pyridine. It can be carried out in the presence of an organic nitrogen base, and the organic base can act simultaneously as a solvent. It is convenient to use the stoichiometric amount in a stoichiometric amount, otherwise in a slight excess of approximately 20 mol% or less of one or the other reactants. If the process is carried out without solvent in the presence of an organic base, it is recommended to use an excessively large amount of the organic base. In general, the reaction temperature is from (-80) to 150 ° C, preferably (-30 ° C) to the boiling point of the reaction mixture. Enamine carboxylates of formula (V) are also novel and can also be prepared from aniline derivatives of formula (XV) according to methods known per se, for example Scheme R). R): The reaction of compounds XX and XIX is preferably anhydrous inert aprotic solvents, for example halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride and chlorobenzene, aromatic hydrocarbons such as benzene, toluene and xylene, diethyl ether, dibutyl And in the presence of aliphatic or cyclic ethers such as ether, 1,2-dimethoxyethane, tetrahydrofuran and dioxane. The reaction temperature for this reaction (the reaction of compounds XX and XIX) is generally approximately 70 to 140 ° C., in particular 100 to 120 ° C. The reaction of compound XII with XIX is generally carried out in the absence of solvent [eg, J. Soc. Dyes Col. 42, 81 (1926), Ber. 64, 970 (1931); Org. Synth., Coll. Vol. IV, 80 (1963) and J. Am. Chem. Soc. 70, 2402 (1948)] or amino decomposition in anhydrous anhydrous solvents / diluents, especially aprotic solvents, for example aromatics such as toluene and xylene, halogenated aromatics such as chlorobenzene. Alkaline catalysts such as high boiling amines [eg, Helv. Chim. Acta 11 , 779 (1928) and US Pat. No. 2,416,738] or in the presence of pyridine is recommended. The reaction temperature is preferably about 20 to 160 ° C. The starting compounds are conveniently used in stoichiometric amounts in each case, or else the method is carried out in a slight excess of up to approximately 10 mol% of one or the other reactants. If the process is carried out in the presence of an alkaline catalyst, 0.5 to 2 times molar amount of catalyst is sufficient, based on the amount of one of the extracts. Subsequent reaction of the resultant compound of formula XXI with amine HN (R 3 ) -COOL 1 is advantageously carried out at atmospheric pressure absolutely in anhydrous solvents / diluents, particularly preferably in the presence of an acidic catalyst. To prepare enamine carboxylate V, wherein R 3 = amino, it is recommended to use compound XXII and a protected amino group (eg hydrazone). Suitable solvent / diluents are in particular organic liquids which can be mixed with water to give an azeotropic mixture, for example aromatics such as benzene, toluene and xylene, or halogenated hydrocarbons such as carbon tetrachloride and chlorobenzene. Suitable catalysts are, in particular, strong inorganic acids such as sulfuric acid, organic acids such as phosphorus containing acids such as p-toluenesulfonic acid, orthophosphoric acid and polyphosphoric acid, and acidic cation exchangers such as "Amberlyst 15" (Fluka). Generally, the reaction temperature is approximately 70 to 150 ° C., but in order to remove the generated reaction water, the process is conveniently carried out at the boiling point of the reaction mixture. Compounds of formula (XIII), (XVI), (XVII) and (XXI) are also novel. They can also be prepared from methods known per se, in particular advantageously from compounds of formula XIX. S): Hydrolysis of Process Product XVI Using “Phosgenation” of Formula XIX and Ammonia (derivative): The method can be carried out absolutely in anhydrous solvents / diluents or in the absence of solvents. The amino groups are preferably converted to isocyanate groups by phosgene or trichloromethyl chloroformate. Suitable solvents / diluents are in particular aprotic solvents, for example aromatics such as toluene and xylene, halogenated hydrocarbons such as methylene chloride, chloroform, 1,2-dichloroethane and chlorobenzene, 1,2-dimethoxyethane, tetra Aliphatic or cyclic ethers such as hydrofuran and dioxane, esters such as ethyl acetate, and mixtures thereof. Depending on the aniline derivative XIX used, it may be advantageous to add a base such as triethylamine in an amount of from 0.5 to 2 times the molar amount, for example based on the amount of compound XIX. Phenyl isocyanate XVI is generally formed at 50 ° C. to the boiling point of the reaction mixture, which can subsequently be reacted with ammonia or reactive ammonia derivatives to give the phenylurea derivative XIII. T): Reaction with alkali metal cyanates: M + is the same as metal ions, especially alkali metal ions such as sodium and potassium. The reaction is generally carried out in an inert solvent / diluent, for example aromatic hydrocarbons such as toluene and xylene, aliphatic or cyclic ethers such as tetrahydrofuran and dioxane, lower alcohols such as methanol and ethanol, water or mixtures thereof. Although the amount of cyanate is not critical, an equivalent amount or more of the aniline compound XIX and cyanate is required for the complete reaction, but up to approximately 100 mole% of excess isocyanate may also be advantageous. The reaction temperature is generally from 0 ° C. to the boiling point of the reaction mixture. U): Reaction with ester L 4 -O-CO-L 5 : L 5 is halogen, preferably chlorine or bromine, C 1 -C 4 -alkoxy or phenoxy. Suitable solvents / diluents are in particular aprotic solvents, for example aromatic hydrocarbons such as toluene and xylene, halogenated hydrocarbons such as methylene chloride, chloroform, 1,2-dichloroethane and chlorobenzene, 1,2-dimethoxyethane, Aliphatic or cyclic ethers such as tetrahydrofuran and dioxane, esters such as ethyl acetate, alcohols such as methanol and ethanol or water. Mixtures of organic solvents and water are also suitable. The process preferably comprises a base such as an alkali metal hydroxide, an alkali metal carbonate or an alkali metal alcoholate such as sodium hydroxide, sodium carbonate, sodium methanolate and sodium ethanolate, or tertiary amines such as pyridine and triethylamine In the presence of If desired, a catalyst, for example Lewis acid, such as antimony trichloride can also be added. Starting compounds and bases are conveniently used in approximately stoichiometric amounts, but one or more other components may be present in excess of approximately 100 mol% or less. Generally, the amount of catalyst is from 1 to 50 mol%, preferably from 2 to 30 mol%, based on the amount of aniline compound XIX used. In general, the reaction temperature is successfully carried out at (-40) to the boiling point of the reaction mixture. Aniline compounds of formula XIX are also novel. These are generally synthesized by hydrogenation from the corresponding nitro compound XXIII or from the aniline of formula XXIV to the corresponding aniline compound of formula XIX according to method F). Nitro compounds of compound XXIII are also novel. These can be synthesized by methods known per se, for example by nitriding the corresponding benzylamines. Compounds of formulas VII, X, XI, XII, XIV, XV, XVIII, XIX, XXIV can be synthesized in a manner known per se (for example, in International Application Publication No. 92/02088 and German Patent Publication No. 42 37 920). If not otherwise indicated, all of the methods described above are conveniently carried out under atmospheric pressure or under the original pressure of the reaction mixture concerned. Depending on the substitution form of the target compound, it may be advisable to change the order of each reaction step so that no specific by-products are formed or in small amounts. Generally, the reaction mixture is worked up by itself known methods, for example by removing the solvent, working up the residue by partitioning the residue in a mixture of water and a suitable organic solvent and working up the organic phase to give the product. Benzylhydroxylamines of formula (I) may contain one or more chiral centers and are generally obtained in the form of enantiomers or diastereomer mixtures unless the synthesis is tailored to yield only one particular isomer. If desired, the mixture can be separated by conventional methods for separation purposes, for example by crystallization or chromatography on optically active adsorbates, to obtain absolutely pure isomers. Pure optically active isomers can also be prepared, for example, from the corresponding optically active starting materials. Benzylhydroxylamine I, in which R 3 , R 7 or R 8 is hydrogen, can be converted into its salt, preferably its alkali metal salt, in a manner known per se. Salts of compound I in which the metal ions are not alkali metal ions can be prepared by double decomposition of the corresponding alkali salts, and the ammonium, phosphonium, sulfonium and sulfoxium salts are ammonia, phosphonium hydroxide, sulfonium hydroxide or sulfonate hydroxide. It may be prepared in a conventional manner with oxonium. Compound I and its agrochemically useful salts in the form of isomeric mixtures and in the pure isomeric form are suitable as herbicides. Herbicidal compositions comprising Compound I, in particular, have very good plant control on the non-crop area at high application rates. They act on broad-leaved weeds and grass weeds in crops such as wheat, rice, corn, oil and cotton without significant adverse effects on crop plants. In particular, this effect is seen at low rates of application. Depending on the application method in question, the herbicidal composition comprising Compound I or the same may also be used in many crops to remove undesirable plants. Suitable crops are for example: Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Beta vulgaris species. Altishima (Beta vulgaris spp.altissima), a beta vulgaris species. Beta vulgaris spp.rapa, Brassica napus var.napus, Brassica napus var. Napobrasica, Brassica rapa strain Sylvestris (Brassica rapa var.silvestris), Camellia sinensis, Carthamus tinctorius, Carya illinoinensis Citrus limon, Citrus sinensis , Copea arabica [Coffea canephora, Copea liberica], Cucumis sativus, Cynodon dactylon, Doucus carota (Daucus carota), Elaeis guineensis, Fragararia vesca, Glycine max, Gossypium hirsutum [Gossypium arboreum, Gossip herba Gossypium herbaceum, Gossypium vitifolium], Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Humulus lupulus Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicicon Lycopersicum Lycopersic ), Malus spp., Manihot esculenta, Medica sativa, Musa spp., Nicotiana tabacum [Nicotiana rutica) (N. rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies , Pinus spp., Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Rives sylvestre ), Ricinus communis, Saccharum officinarum, Secale cereale, Solanum tuberosum, Sorghum bicolor [Sorch S. vulgare], Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticum durum, Vicia pava Vicia faba), Vitis vinifera and Zea mays. In addition, Compound I can also be used in crops that are resistant to the action of herbicides as a result of breeding, including genetic engineering methods. Moreover, benzylhydroxylamine I is also suitable for drying and / or dead leaves of plants. As desiccants, they are particularly suitable for drying the upper parts of crops such as potatoes, rapeseeds, sunflowers and kidney beans. This allows these major crops to be harvested completely by machine. Also of interest economically is the ease of harvesting, which allows for temporary concentration or deterioration of ten attachments to trees for citrus, olive or other species and for various fruits, succulents and bark fruits. . The same mechanism, i.e., promoting breakaway tissue formation between the stem part of the plant and the leaves or fruits, is essential for useful plants, especially the dead leaves targeted in cotton. In addition, shortening the ripening time interval of each cotton plant improves the quality of the fiber after harvesting. Compound I or a composition comprising the same can be used, for example, directly sprayable aqueous solutions, powders, suspensions, highly concentrated aqueous, oily or other suspending agents, or dispersions, emulsions, oily dispersions, pastes, dust compositions, dispersions It can be used by spraying, spraying, dust spraying, spraying or watering in the form of a composition or granules. The form of use depends entirely on the intended purpose, but in each case, the active ingredient according to the invention should be dispersed very finely if possible. Suitable inert adjuvants are mainly middle to high boiling mineral oil fractions such as kerosene or diesel oils, as well as aliphatic such as coultar and vegetable or animal oils, paraffins, tetrahydronaphthalenes, alkylated naphthalenes and derivatives thereof, alkylated benzenes and derivatives thereof. Strong polar solvents such as cyclic and aromatic hydrocarbons, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as cyclohexanone, amines such as N-methylpyrrolidone and water. Aqueous use forms can be prepared by adding water from emulsion concentrates, dispersions, pastes, wettable powders or water dispersible granules. In order to produce an emulsion, a paste or an oily dispersion, the component itself or a component dissolved in an oil or a solvent can be homogenized in water using a wetting agent, an adhesive, a dispersant or an emulsifier. Alternatively, concentrates may be prepared comprising the active ingredient, wetting agent, adhesive, dispersant or emulsifier, and optionally a solvent or oil, which concentrates are suitable for dilution with water. Examples of suitable surface active materials (adjuvant) include aromatic sulfonic acids such as ligninsulfonic acid, phenolsulfonic acid, naphthalenesulfonic acid and dibutylnaphthalenesulfonic acid, and alkali metals, alkaline earth metal and ammonium salts of fatty acids, alkyl sulfonates and alkylaryl sulfonates, Alkyl sulfates, lauryl ether sulfates and fatty alcohol sulfates, and salts of sulfated hexadecanol, heptadecanol and octadecanol, and salts of fatty alcohol glycol ethers, sulfonated naphthalenes and derivatives thereof with formaldehyde Condensation products of, condensation products of naphthalene or naphthalenesulfonic acids with phenols and formaldehyde, polyoxyethylene octylphenol ethers, ethoxylated isooctylphenols, ethoxylated octylphenols and ethoxylated nonylphenols, alkylphenol polyglycol ethers, tributylphenyl Polyglycol ether, alkylaryl polyether alcohol, isotridecyl Alcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers or polyoxypropylene alkyl ethers, lauryl alcohol polyglycol ether acetate, sorbitol esters, lignin-sulfite waste solution or a cellulose. Powder, dispersion and dust compositions can be prepared by mixing or co-pulverizing the active ingredient with the solid carrier. For example, coated granules, impregnated granules and homogeneous granules can be prepared by binding the active compound to a solid carrier. Solid carriers are inorganic earths, such as silica acids, silica gels, silicates, talc, kaolin, limestone, lime, chalk, church clay, loess clay, clay, dolomite, diatomaceous earth, calcium sulfate and magnesium sulfate, magnesium oxide , Pulverized plastics, fertilizers such as ammonium sulphate, ammonium phosphate, ammonium nitrate and urea, and vegetable products such as grains, bark meal, wood meal and peanut flour, and cellulosic powders or other solid carriers. The concentration of the active ingredient I in the preparations ready for use can vary within a wide range, in general the preparations comprise, for example, 0.001 to 98% by weight, preferably 0.01 to 95% by weight of one or more active ingredients do. The active ingredient is used in a purity of 90 to 100%, preferably 95 to 100% (by NMR spectrum). The formulation examples below illustrate the preparation of such products. I. Compound No. It.01 20 parts by weight of 80 parts by weight of alkylated benzene, 10 parts by weight of 8 to 10 moles of ethylene oxide and 1 mole of oleic acid N-monoethanolamide, 5 parts of calcium salt of dodecylbenzenesulfonic acid Part and 5 parts by weight of an adduct of 40 moles of ethylene oxide and 1 mole of castor oil. This solution is poured into 100,000 parts by weight of water and finely dispersed to obtain an aqueous dispersion containing 0.02% by weight of active ingredient. II. 20 parts by weight of compound number 1.02 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of an addition of 7 moles of ethylene oxide and 1 mole of isooctylphenol, and 40 moles of ethylene oxide and 1 mole of castor oil It is dissolved in a mixture consisting of 10 parts by weight of an adduct with. This solution is poured into 100,000 parts by weight of water and finely dispersed to obtain an aqueous dispersion containing 0.02% by weight of active ingredient. III. 20 parts by weight of compound number 1.03 is dissolved in a mixture consisting of 25 parts by weight of cyclohexanone, 65 parts by weight of a mineral oil fraction having a boiling point of 210 to 280 ° C, and 10 parts by weight of an adduct of 40 moles of ethylene oxide and 1 mole of castor oil. This solution is poured into 100,000 parts by weight of water and finely dispersed to obtain an aqueous dispersion containing 0.02% by weight of active ingredient. IV. 20 parts by weight of active ingredient No. 1.05 are thoroughly mixed with 3 parts by weight of sodium salt of diisobutylnaphthalene-α-sulfonic acid, 17 parts by weight of sodium salt of lignin sulfonic acid obtained from the sulfite waste liquor and 60 parts by weight of silica gel powder, and the mixture is a hammer mill. Pulverize in. The mixture is finely dispersed in 20,000 parts by weight of water to obtain a spray liquid containing 0.1% by weight of the active ingredient. V. 3 parts by weight of active ingredient No. 1.04 are mixed with 97 parts by weight of finely divided kaolin. Dust compositions containing 3% by weight of active ingredient are obtained in the above process. VI. Active ingredient number 1.16 20 parts by weight intimately mixed with 2 parts by weight of calcium salt of dodecylbenzenesulfonic acid, 8 parts by weight of fatty alcohol polyglycol ether, 2 parts by weight of sodium salt of phenol / urea / formaldehyde condensate and 68 parts by weight of paraffin mineral oil do. A stable oily dispersion is obtained. VII. 1 part by weight of active ingredient No. 1.17 is dissolved in a mixture consisting of 70 parts by weight of cyclohexanone, 20 parts by weight of ethoxylated isooctylphenol and 10 parts by weight of ethoxylated castor oil. Obtain a stable emulsion concentrate. VIII. 1 part by weight of active ingredient No. 1.18 is dissolved in a mixture consisting of 80 parts by weight of cyclohexanone and 20 parts by weight of Uniferol® EL (a nonionic emulsifier based on ethoxylated castor oil). Obtain a stable emulsion concentrate. The active ingredient I or herbicidal compositions comprising the same may be applied before or after germination. If the active ingredient is less resistant to certain crops, the sprayer is used so that the leaves of sensitive crops are hardly affected, if possible, while allowing the active ingredient to reach the leaves of unnecessary plants that grow under these crops or on exposed soil surfaces. Application techniques can be used to spray the herbicide composition using a group (post-directed, lay-by). The application rate of the active ingredient I depends on the control target, the time of year, the target plant and the growth stage, and the active ingredient (a.i.) is preferably 0.001 to 3.0 kg / ha, in particular 0.01 to 1 kg / ha. In order to broaden the range of action and obtain a synergistic effect, benzylhydroxylamine I can be mixed with many representative other herbicide groups or groups of growth regulating active ingredients and applied simultaneously. Examples of suitable mixture components include 1,2,4-thiadiazole, 1,3,4-thiadiazole, amide, aminophosphoric acid and derivatives thereof, aminotriazole, analyde, aryloxy- / heteroaryloxy Alkanolic acid and derivatives thereof, benzoic acid and derivatives thereof, benzothiadiazinone, 2- (heteroyl / aroyl) -1,3-cyclohexanedione, heteroaryl aryl ketones, benzylisoazolidinone, meta-CF 3 -Phenyl derivatives, carbamates, quinolinecarboxylic acids and derivatives thereof, chloroacetanilide, cyclohexane-1,3-dione derivatives, diazines, dichloropropionic acid and derivatives thereof, dihydrobenzofuran, dihydrofuran-3- On, dinitroaniline, dinitrophenol, diphenyl ether, bipyridyl, halocarboxylic acid and derivatives thereof, urea, 3-phenyluracil, imidazole, imidazolinone, N-phenyl-3,4,5 , 6-tetrahydrophthalimide, oxadiazole, oxirane, phenol, aryloxy- and he Roaryloxyphenoxypropionic acid ester, phenylacetic acid and derivatives thereof, 2-phenylpropionic acid and derivatives thereof, pyrazole, phenylpyrazole, pyridazine, pyridine-carboxylic acid and derivatives thereof, pyrimidyl ether, sulfonamide, sulfonyl Urea, triazine, triazinone, triazolinone, triazolecarboxamide and uracil. Furthermore, it may be advantageous to apply Compound I alone or in admixture with other herbicides, in addition to other crop protection compositions, such as pest or plant pathogenic fungal or bacterial control compositions. Also of note is compatibility with mineral salt solutions used in the nutrition and treatment of trace element deficiencies. Non-phytotoxic oils and oil concentrates may be added. Example 1 3- (4-chloro-3-methoxyaminomethylphenyl) -1-methyl-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione (Compound No. 1.01) Triethylsilane (1.9 mL) was added 3- (4-chloro-3-methoxyiminomethylphenyl) -1-methyl-6-trifluoro-methyl-1 in a mixture of 30 mL dichloromethane and 50 mL trifluoroacetic acid. To the solution of 2,3,4-tetrahydropyrimidine-2,4-dione (3.6 g) was added dropwise. The mixture was stirred at rt for 20 h before the solvent was evaporated off. The residue was taken up with 200 mL of dichloromethane and the organic phase was washed four times with in each case 50 mL of water, dried over sodium sulphate and finally concentrated. Crystallization using diisopropyl ether and petroleum ether gave the title compound (melting point 83-85 ° C.). Example 2 3- (4-chloro-3-ethoxyaminomethylphenyl) -1-methyl-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione (Compound No. 1.02) Borane-pyridine complex (3 mL) and 10% hydrochloric acid (30 mL) were added to 3- (4-chloro-3-ethoxyiminomethylphenyl) -1-methyl-6-trifluoro- in 40 mL of ethanol at 0 ° C. Successively dropwise addition to a solution of methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione (3.8 g). During 16 hours, additional 12 ml of borane-pyridine complex was added. Subsequently, the solution was stirred at reflux for 4 hours and then the solvent was evaporated off. The residue was taken up with 200 ml of dichloromethane. The organic phase was washed twice with 50 ml of water in each case, then dried over sodium sulphate and finally concentrated. This gave the title compound as an oil. Example 3 3- (3- [acetyl (methoxyamino) methyl] -4-chloromethyl) -1-methyl-6-trifluoro-1,2,3,4-tetrahydropyrimidine-2,4-dione ( Compound number 1.04) 3- (4-chloro-3-methoxyaminomethylphenyl) -1-methyl-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione in 30 ml tetrahydrofuran (1.6 g) was added dropwise to a suspension of sodium hydride (0.17 g) in 50 mL tetrahydrofuran. After 1 hour, acetyl chloride (0.4 g) in 20 mL tetrahydrofuran was added. The mixture was stirred at rt for 20 h and subsequently treated with water (100 mL). The desired product was extracted from the aqueous phase using 2 x 100 mL of dichloromethane. The combined organic phases were washed three times with water, dried over sodium sulphate and the solvent was removed. Silica gel chromatography (eluent: dichloromethane / ethylacetate = 9: 1) and crystallized using petroleum ether to give the title compound (melting point 160-161 ° C.). Example 4 3- (3-[(methoxymethylamino) methyl] -4-chlorophenyl) -1-methyl-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione (Compound No. 1.06) 3- (3-bromomethyl) -4-chloro-2-fluorophenyl) -1-methyl-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione (0.005 mol) was added to a mixture of methoxyethylamine (0.06 mol), potassium carbonate (0.012 mol) and 100 ml of dimethylformamide. After 5 hours at room temperature, the reaction solution was concentrated. After the residue was treated with 100 ml of methylene chloride, the organic phase was washed three times in each case with 30 ml of water, then dried over sodium sulfate and finally concentrated. The desired valuable product was obtained by adding petroleum ether to the resulting oil. Example 5 3- (3- [ethoxycarbonylaminooxymethyl] -4-chloro-6-fluorophenyl) -1-amino-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine- 2,4-dione (Compound No. It.10) 0.9 g of carbonyldiimidazole was added to 3- (3-hydroxymethyl-4-chloro-6-fluorophenyl) -1-amino-6-trifluoromethyl-1,2,3 in 100 ml of tetrahydrofuran. To a solution of 1.8 g of, 4-tetrahydropyrimidine-2,4-dione was added. After the reaction mixture was stirred for 1 hour, 0.58 g of N-ethoxycarbonylhydroxylamine was added. Subsequently, the mixture was stirred for an additional 14 hours at 20 ° C. and then the solvent was removed by evaporation. The residue was taken up in 100 ml of methylene chloride. The resulting organic phase was washed with water, dried over sodium sulphate and finally concentrated. The crude product was purified by chromatography on silica gel (eluent: methylene chloride) (yield 0.2 g). In addition to the compounds described above, other benzylhydroxylamines I prepared or prepared by similar methods are shown in Table 4 below. <Formula I> Example of use (herbicidal activity) The herbicidal activity of benzylhydroxylamine I is shown in the following greenhouse experiments: The culture pot used was a plastic pot containing loam sand having about 3.0% humus soil as subsoil. Seeds of the test plants were sown by species. In the case of pre-germination treatment, the active ingredient suspended or emulsified in water was applied directly after seeding with a fine dispersion nozzle. After slightly irrigating the pots to promote germination and growth, they were covered with a clear plastic hood until the plants took root. This cover will result in a uniform germination of the test plant if it is not damaged by the active ingredient. For post-germination treatment, the test plants were first grown to a height of 3-15 cm, depending on the growth form, and then treated with the active ingredients suspended or emulsified in water. For this purpose, the test plants were sown directly in pots and grown in the pots, or separately grown first as seedlings and planted in test pots a few days before treatment. Application rates for post-germination treatments were 0.0078 and 0.0039 kg / ha of active ingredient, respectively. Depending on the species, the plants were kept at 10-25 ° C or 20-35 ° C. The trial period lasted 2-4 weeks. During this time, the plants were cared for and evaluated their response to various treatments. Plants were rated on a scale of 0-100. In this case 100 indicates that the plant has not germinated or at least the ground part has completely died, and 0 indicates that it is intact or has grown normally. Plants used in greenhouse experiments consist of the following species: BotanyCommon name Abutilon theophrastiVelvet leaf Gallium aparineCatchweed Bedstraw Sinapis albaWhite mustard Solanium nigrumBlack nightshade Veronica subspeciesTarmac Flock (Speedwell) At application rates of 0.0156 or 0.0078 kg / ha of active ingredient, compound number 1.03 was very effective against abutylon ceoplasti, solanium nigrum and various veronica species when used after germination. At application rates of 3.9 or 1.9 g / ha of active ingredient, compound number It.10 was very effective against potassium aparin, cinapis alba and solanium nigrum when used after germination. <Example of use (dry / dead leaf activity)> The test plants used were young 4-leaf (no leaves) cotton plants grown in greenhouse conditions (50-70% relative humidity; night / day temperature 20/27 ° C.). The leaves of the young cotton plants were treated with an aqueous formulation of the active ingredient (0.15% by weight of fatty alcohol alkoxylate Flurafac LF 700 added based on the spray mixture). The amount of water used was 1000 L / ha (converted). After 13 days, the number of leaves lost and the extent of dead leaves were determined in%. No leaf loss occurred in untreated control plants.
权利要求:
Claims (16) [1" claim-type="Currently amended] An agriculturally useful salt of formula (I) wherein benzylhydroxylamine of formula (I) and R 3 , R 7 and / or R 8 are hydrogen. <Formula I> Where X is —N (R 7 ) —O—, which may be bonded to R 8 through oxygen or nitrogen, Y is oxygen or sulfur, R 1 is halogen, cyano, nitro or trifluoromethyl, R 2 is hydrogen or halogen, R 3 is hydrogen, amino or methyl, R 4 is hydrogen, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulfinyl or C 1 -C 6 -alkyl Sulfonyl, R 5 is hydrogen, halogen or C 1 -C 6 -alkyl, R 6 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl or C 2 -C 6 -alkenyl, R 7 is hydrogen, C 1 -C 6 -alkyl, C 3 -C 8 -cycloalkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, ( C 1 -C 6 -alkyl) carbonyl, (C 3 -C 6 -alkenyl) carbonyl, (C 3 -C 6 -alkynyl) carbonyl, (C 1 -C 6 -alkoxy) carbonyl, ( C 2 -C 6 -alkenyloxy) carbonyl, (C 2 -C 6 -alkynyloxy) carbonyl, (C 1 -C 6 -alkylthio) carbonyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -alkylcarbamoyl, each of the last 14 radicals mentioned Nitro, cyano, halogen, C 3 -C 8 -cycloalkyl, hydroxyl, C 1 -C 6 -alkoxy, C 3 -C 8 -cycloalkoxy, C 3 -C 6 -alkenyloxy, C 3- C 6 -alkynyloxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, (C 1 -C 6 -alkyl) carbonyl, (C 1 -C 6 -alkyl) carbonyloxy, C 1 -C 6 -alkyl sulfinyl, C 1 -C 6 -alkyl sulfonyl, C 1 -C 6 - alkylidene aminoxy when, C 1 -C 6 -alkyl-carbamoyl, 1 to 3 substituents unsubstituted or selected from the group consisting of halogen, nitro, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy and C 1 -C 6 -haloalkyl A phenyl, phenoxy or phenylsulfonyl group which can be bonded, The heterocycle may be saturated, partially or fully unsaturated or aromatic, if necessary halogen, nitro, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -halo Selected from the group consisting of two oxygen atoms, two sulfur atoms and three nitrogen atoms to which one to three substituents selected from the group consisting of alkyl and (C 1 -C 6 -alkyl) carbonyl can be bonded 3- to 7-membered heterocyclyl or heterocyclyloxy group having 1 to 3 heteroatoms, -CO-Z 1 R 9 , -OCO-Z 1 R 9 or -N (R 9 ) R 10 groups 1 to 3 substituents selected from the group consisting of R 7 is C 3 -C 8 -cycloalkylcarbonyl, phenylcarbonyl, phenylsulfonyl or phenylcarbamoyl, wherein these four radicals are unsubstituted or halogen, nitro, cyano, C 1 -C 6- 1 to 3 substituents selected from the group consisting of alkyl, C 1 -C 6 -alkoxy and C 1 -C 6 -haloalkyl may be bonded, R 8 is hydrogen, C 1 -C 6 -alkyl, C 3 -C 8 -cycloalkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -alkenyl or C 3 -C 6 -alkynyl, Each of the last five radicals mentioned Nitro, cyano, halogen, C 3 -C 8 -cycloalkyl, hydroxyl, C 1 -C 6 -alkoxy, C 3 -C 8 -cycloalkoxy, C 3 -C 6 -alkenyloxy, C 3- C 6 -alkynyloxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsul Ponyl, C 1 -C 6 -alkylideneamioxy, 1 to 3 substituents unsubstituted or selected from the group consisting of nitro, cyano, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy and C 1 -C 6 -haloalkyl Phenyl, phenoxy or phenylsulfonyl group to which can be bonded, The heterocycle may be saturated, partially or fully unsaturated or aromatic, if necessary halogen, nitro, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy C 1 -C 6 -haloalkyl And one to three substituents selected from the group consisting of (C 1 -C 6 -alkyl) carbonyl can be bonded to one selected from the group consisting of two oxygen atoms, two sulfur atoms and three nitrogen atoms 3- to 7-membered heterocyclyl or heterocyclyloxy group having 1 to 3 heteroatoms, -CO-Z 2 R 11 , -OCO-Z 2 R 11 or -N (R 11 ) R 12 groups One to three substituents selected from the group consisting of may be bonded, Z 1 is a chemical bond, oxygen, sulfur or -N (R 10 )-, Z 2 is a chemical bond, oxygen, sulfur or -N (R 12 )-, R 9 , R 11 are independently of each other hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 8 -cycloalkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, (C 1 -C 6 -alkoxy) carbonyl-C 1 -C 6 -alkyl, phenyl or phenyl-C 1 -C 6 -Phenyl, and the phenyl ring of the phenyl group and the phenylalkyl group is unsubstituted, nitro, cyano, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy or (C 1 1 to 3 substituents selected from the group consisting of -C 6 -alkyl) carbonyl may be bonded, or In each case Z 1 and R 9 and / or Z 2 and R 11 are joined together through nitrogen and are one to three heteroatoms selected from the group consisting of two oxygen atoms, two sulfur atoms and three nitrogen atoms 3- to 7-membered heterocycle having a heterocycle, which may be saturated, partially or fully unsaturated, or aromatic, if necessary nitro, cyano, halogen, C 1 -C 6 -alkyl, C 1- 1 to 3 substituents selected from the group consisting of C 6 -haloalkyl and C 1 -C 6 -alkoxy may be bonded, R 10 , R 12 are independently of each other hydrogen, hydroxyl, C 1 -C 6 -alkyl, C 3 -C 8 -cycloalkyl or C 1 -C 6 -alkoxy. [2" claim-type="Currently amended] The benzylhydroxylamine of formula I according to claim 1, wherein the substituents have the following meanings. Y is oxygen, R 1 is halogen or cyano, R 2 is hydrogen, fluorine or chlorine, R 3 is amino or methyl, R 4 is C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl or C 1 -C 6 -alkylsulfonyl, R 5 is hydrogen or halogen, R 6 is hydrogen or C 1 -C 4 -alkyl, R 7 is hydrogen, C 1 -C 6 -alkyl, C 3 -C 8 -cycloalkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, ( C 1 -C 6 -alkyl) carbonyl, (C 3 -C 6 -alkenyl) carbonyl, (C 3 -C 6 -alkynyl) carbonyl, (C 1 -C 6 -alkoxy) carbonyl, ( C 2 -C 6 -alkenyloxy) carbonyl, (C 2 -C 6 -alkynyloxy) carbonyl, (C 1 -C 6 -alkylthio) carbonyl, C 1 -C 6 -alkylcarbamoyl Each of the 13 radicals mentioned Nitro, cyano, halogen, C 3 -C 8 -cycloalkyl, hydroxyl, C 1 -C 6 -alkoxy, C 3 -C 8 -cycloalkoxy, C 3 -C 6 -alkenyloxy, C 3- C 6 -alkynyloxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsul Ponyl, C 1 -C 6 -alkylideneaminox, and -CO-Z 1 R 9 , -OCO-Z 1 R 9 or -N (R 9 ) R 10 groups 1 to 2 substituents selected from the group consisting of may be bonded; R 8 is hydrogen, C 1 -C 6 -alkyl, C 3 -C 8 -cycloalkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -alkenyl or C 3 -C 6 -alkynyl, If necessary, each of the last mentioned radicals Nitro, cyano, halogen, C 3 -C 8 -cycloalkyl, hydroxyl, C 1 -C 6 -alkoxy, C 3 -C 8 -cycloalkoxy, C 3 -C 6 -alkenyloxy, C 3- C 6 -alkynyloxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsul Ponyl, C 1 -C 6 -alkylideneaminox, and -CO-Z 2 R 11 , -OCO-Z 2 R 11 or -N (R 11 ) R 12 groups One to three substituents selected from the group consisting of may be bonded, Z 1 is a chemical bond, oxygen, sulfur or -N (R 10 )-, Z 2 is a chemical bond, oxygen, sulfur or -N (R 12 )-, R 9 , R 11 are independently of each other hydrogen, C 1 -C 6 -alkyl, C 3 -C 8 -cycloalkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl or (C 1 -C 6 -alkoxy) carbonyl-C 1 -C 6 -alkyl, or In each case Z 1 and R 9 and / or Z 2 and R 11 are joined together through nitrogen and are one to three heteroatoms selected from the group consisting of two oxygen atoms, two sulfur atoms and three nitrogen atoms 3- to 7-membered heterocycles with heterocycles which may be saturated, partially or fully unsaturated or aromatic, if necessary nitro, cyano, halogen, C 1 -C 6 -alkyl, C 1 -C 1 to 3 substituents selected from the group consisting of 6 -haloalkyl and C 1 -C 6 -alkoxy may be bonded, R 10 , R 12 are independently of each other hydrogen or C 1 -C 6 -alkyl. [3" claim-type="Currently amended] Use of the benzylhydroxylamine of formula (I) or agriculturally useful salt of formula (I) as herbicide or for drying and / or dead leaves of plants. [4" claim-type="Currently amended] At least one benzylhydroxylamine of formula (I) or at least one agriculturally useful salt of formula (I), at least one inert liquid and / or solid carrier, and, if necessary, at least one Herbicide composition comprising a surfactant. [5" claim-type="Currently amended] At least one benzylhydroxylamine of formula (I) or at least one agriculturally useful salt of formula (I), at least one inert liquid and / or solid carrier in an amount having a drying and / or dead leaf action of the plant And, if necessary, a composition for drying and / or dead leaves of plants comprising at least one surfactant. [6" claim-type="Currently amended] At least one benzylhydroxylamine of formula (I) or at least one agriculturally useful salt of formula (I), at least one inert liquid and / or solid carrier, and, if necessary, at least one A method of making a composition that is active with a herbicidal phase comprising mixing a surfactant. [7" claim-type="Currently amended] At least one benzylhydroxylamine of formula (I) or at least one agriculturally useful salt of formula (I), at least one inert liquid and / or solid carrier in an amount having a drying and / or dead leaf action of the plant And, if desired, a method for producing a composition having a drying and / or dead leaf action of a plant comprising mixing at least one surfactant. [8" claim-type="Currently amended] Growth of an undesired plant comprising causing an active amount of at least one benzylhydroxylamine of formula (I) or at least one agriculturally useful salt of formula (I) to act on the plant, its environment or seeds How to regulate. [9" claim-type="Currently amended] Drying of a plant comprising causing the plant to dry and / or to have a dead leaf action in which at least one benzylhydroxylamine of formula (I) or at least one agriculturally useful salt of formula (I) acts on the plant And / or the dead leaf method. [10" claim-type="Currently amended] Enamine esters of formula IV: Where L 1 is C 1 -C 6 -alkyl or phenyl, Substituents R 1 to R 8 are as defined in claim 1. [11" claim-type="Currently amended] Enamine carboxylate of formula (V): Where L 1 is C 1 -C 6 -alkyl or phenyl, Substituents R 1 to R 8 are as defined in claim 1. [12" claim-type="Currently amended] A phenylurea derivative of the formula Where Substituents R 1 to R 3 and R 6 to R 8 are as defined in claim 1. [13" claim-type="Currently amended] Phenyl isocyanate of formula XVI. Where Substituents R 1 , R 2 and R 6 to R 8 are as defined in claim 1. [14" claim-type="Currently amended] Aniline derivatives of formula Where L 4 is C 1 -C 4 -alkyl or phenyl, Substituents R 1 , R 2 and R 6 to R 8 are as defined in claim 1. [15" claim-type="Currently amended] Aniline compounds of formula Where Substituents R 1 , R 2 and R 6 to R 8 are as defined in claim 1. [16" claim-type="Currently amended] Nitro compound of formula XXIII. Where Substituents R 1 , R 2 and R 6 to R 8 are as defined in claim 1.
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同族专利:
公开号 | 公开日 IL122686D0|1998-08-16| EP0836594B1|2001-03-07| WO1997002253A1|1997-01-23| JPH11508574A|1999-07-27| PL324524A1|1998-06-08| CZ2698A3|1998-07-15| MX9800081A|1998-11-29| EP0836594A1|1998-04-22| BR9609306A|1999-06-15| TR199800010T1|1998-05-21| HU9802434A2|1999-01-28| AU6305696A|1997-02-05| CA2223111A1|1997-01-23| US6057269A|2000-05-02| CN1192737A|1998-09-09|
引用文献:
公开号 | 申请日 | 公开日 | 申请人 | 专利标题
法律状态:
1995-07-06|Priority to DE19524617.9 1995-07-06|Priority to DE1995124617 1996-04-26|Priority to DE19616719.1 1996-04-26|Priority to DE1996116719 1996-06-27|Application filed by 스타르크, 카르크, 바스프 악티엔게젤샤프트 1999-04-15|Publication of KR19990028722A
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申请号 | 申请日 | 专利标题 DE19524617.9|1995-07-06| DE1995124617|DE19524617A1|1995-07-06|1995-07-06|New tetrahydro:pyrimidinyl-benzyl hydroxylamine derivs. - useful as herbicides, desiccants and defoliants| DE19616719.1|1996-04-26| DE1996116719|DE19616719A1|1996-04-26|1996-04-26|New 3-pyrimidinyl:benzyl-hydroxylamine derivs.| 相关专利
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