 2-cyclohexane-1,3-dione benzoyl derivative
专利摘要:
The benzoyl derivatives of formula I and agriculturally available salts, their preparation methods and their use as herbicides are described. <Formula I> Wherein the substituents L, M, X, Y and n have the meanings defined in claim 1, Q is a cyclohexane-1,3-dione ring of Formula II, which is bonded at the 2-position; <Formula II> (In the meal, R 15 , R 16 , R 18 and R 20 are hydrogen or C 1 -C 4 -alkyl; R 19 is hydrogen, C 1 -C 4 -alkyl or —COOR 14 group; R 17 is hydrogen, C 1 -C 4 -alkyl, C 3 -C 4 -cycloalkyl, wherein these groups are preferably 1 in halogen, C 1 -C 4 -alkylthio or C 1 -C 4 -alkoxy To three substituents), or R 17 is tetrahydropyran-3-yl, tetrahydropyran-4-yl or tetrahydrothiopyran-3-yl, or R 17 and R 20 together form a bond or form a 3 to 6 membered carbocyclic ring) If, however, the Y = C = O, X is not NR 23. 公开号:KR19990044329A 申请号:KR1019980701569 申请日:1996-08-29 公开日:1999-06-25 发明作者:마르티나 오텐；볼프강 폰 데인；스테판 엥겔；레기나 루이제 힐；우베 카르도르프；마르쿠스 포센；페터 플라트；헬무트 발터；카를-오토 베스트팔렌；울프 미쓸리츠 申请人:스타르크, 카르크；바스프 악티엔게젤샤프트； IPC主号:
专利说明:
2-cyclohexane-1,3-dione benzoyl derivative The present invention relates to novel benzoyl derivatives having a herbicidal action, a benzoyl derivative and a process for preparing a composition containing the same, and a use for inhibiting weeds of a benzoyl derivative or a composition containing such a derivative. Herbicidal active 2-aroylcyclohexanedione is described, for example, in EP 283261 EP 90262, EP 135191, EP 186118, EP 186119, EP 186120, EP 319075, WO 9005712, WO 9404524, WO 9408988, JO 3052862 and JO 3120202. ]. However, herbicidal and crop resistance of known compounds are only satisfactory in a limited range. It is an object of the present invention to obtain novel 2-aroylcyclohexanediones with improved properties. The inventors have found that this object is achieved with the benzoyl derivatives of formula (I) and the agriculturally common salts of compound (I). Where L and M are hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 4 -alkoxy, wherein these groups are from 1 to 5 halogens Or unsubstituted or substituted with an atom or C 1 -C 4 -alkoxy), halogen, cyano, nitro,-(A) m -S (O) n R 1 group or-(A) m -CO-R 2 groups; Y is C = O, C = NR 3 , CR 7 -NR 5 R 6 , CR 7 -OR 8 , CR 10 R 11 , CR 7 -SR 8 ; 1,3-dioxanyl or 1,3-dioxolanyl substituted with hydrogen or C 1 -C 4 -alkyl; A group selected from a hetero atom selected from oxygen, sulfur and nitrogen; X is (-CR 12 R 13- ), (-CR 12 R 13 -CR 21 R 22- ), (-CR 12 = CR 13- ), (-CR 12 R 13 -CR 12 = CR 13- ) ; Consisting of NR 23 , wherein the bond between X and Y may be saturated or unsaturated; A is O or NR 14 ; m is 0 or 1; n is 0, 1 or 2; R 1 is C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl or NR 14 ; R 2 is C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or NR 14 ; R 3 is hydrogen, —NR 9 R 4 ; C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -halo Alkenyl, C 2 -C 6 -alkynyl; Mono- to polysubstituted phenyl wherein the substituents are C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkyl, halogen, cyano , Nitro); Mono- to polysubstituted benzyl, wherein the substituents are C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkyl, halogen, cyano , Nitro); Mono- to polysubstituted benzyloxy, wherein the substituents are C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkyl, halogen, cya O, nitro); R 4 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C═O—NR 14 ; Mono- to polysubstituted phenyl wherein the substituents are C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkyl, halogen, cyano , Nitro); Mono- to polysubstituted benzyl, wherein the substituents are C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkyl, halogen, cyano Is selected from nitro); R 9 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C═O—NR 14 ; Mono- to polysubstituted phenyl wherein the substituents are C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkyl, halogen, cyano , Nitro); Mono- to polysubstituted benzyl, wherein the substituents are C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkyl, halogen, cyano Is selected from nitro); R 5 and R 6 independently of one another are hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 1 -C 4 -haloalkyl, C 2 -C 6 -haloalkenyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy; Mono- to polysubstituted phenyl wherein the substituents are C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkyl, halogen, cyano , Nitro); Mono- to polysubstituted benzyl, wherein the substituents are C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkyl, halogen, cyano Is selected from nitro); R 7 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy; Substituted or unsubstituted phenyl, wherein the substituent is selected from 1 to 3 halogens, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, nitro; R 7 and R 21 or R 7 and R 23 or R 7 and R 12 may form a bond; R 8 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 4 -haloalkyl, substituted phenyl, wherein the substituents are C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkyl, halogen, cyano, nitro); Substituted benzyl, wherein the substituent is selected from C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkyl, halogen, cyano, nitro ); R 10 and R 11 are, independently from each other, hydrogen, C 1 -C 6 -alkyl; Unsubstituted or substituted phenyl, wherein the substituent is selected from 1 to 3 halogens, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, nitro; R 10 and R 12 or R 10 and R 23 or R 10 and R 21 may form a bond; R 12 and R 13 are, independently from each other, hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy; Unsubstituted or substituted phenyl, wherein the substituents are C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkyl, halogen, cyano, Selected from nitro); R 14 is C 1 -C 4 -alkyl; R 21 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy; Unsubstituted or substituted phenyl, wherein the substituents are C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkyl, halogen, cyano, Selected from nitro); R 22 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy; Unsubstituted or substituted phenyl, wherein the substituents are C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkyl, halogen, cyano, Selected from nitro); R 23 is hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 1 -C 6 -alkoxy, phenyl or benzyl (which is C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy , Unsubstituted or substituted with C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkyl, halogen, cyano, nitro); Q is a cyclohexane-1,3-dione ring of Formula II, which is bonded at the 2-position; (In the meal, R 15 , R 16 , R 18 and R 20 are hydrogen or C 1 -C 4 -alkyl; R 19 is hydrogen, C 1 -C 4 -alkyl or —COOR 14 group; R 17 is hydrogen, C 1 -C 4 -alkyl, C 3 -C 4 -cycloalkyl, wherein these groups are preferably 1 in halogen, C 1 -C 4 -alkylthio or C 1 -C 4 -alkoxy To three substituents), or R 17 is tetrahydropyran-3-yl, tetrahydropyran-4-yl or tetrahydrothiopyran-3-yl, or R 17 and R 20 together form a bond or form a 3 to 6 membered carbocyclic ring) If, however, the Y = C = O, X is not NR 23. Compounds of Formulas Ia through Ie are obtained by reacting and rearranging a compound of Formula II with a benzoic acid derivative of Formula III. <Scheme 1> In the above scheme, T means halogen or OH, and L, M, X, T and n have the meanings defined above. Acylation, which is the first step in the reaction sequence, is commonly carried out by known methods, for example acid chlorides of formula III (T = Cl) or activated carboxylic acids of formula III (T = OH), for example DCC (Dicyclocarbodiimide) or similar agents known in the literature, such as triphenylphosphine / DEAD = diethyl azodicarboxylate, 2-pyridine disulfide / triphenylphosphine, if appropriate, auxiliaries In the presence of a base, it is carried out by addition to a solution or suspension of cyclohexanedione II. In this case, the reactants and the auxiliary base are used in equimolar amounts for convenience. For example, 1.2 to 1.5 molar amount of slightly excess auxiliary base based on compound II may be advantageous under certain conditions. Suitable auxiliary bases are tertiary alkylamines, pyridine or alkali metal carbonates. The solvent used may be, for example, methylene chloride, dioxane, diethyl ether, toluene, acetonitrile or ethyl acetate. During the addition of the acid chloride, the reaction mixture is preferably cooled to 0 to 10 ° C and then stirred at 20 to 100 ° C, in particular 25 to 50 ° C, until the reaction is complete. The finishing treatment is carried out by conventional methods, for example by pouring the reaction mixture into water and extracting the useful product, for example with methylene chloride. After drying the organic phase and removing the solvent, the crude enol ester can be rearranged without further purification. Examples of preparations for the benzoyl enol esters of cyclohexane-1,3-dione are described, for example, in EP-A 186,118 or US 4,780,127. Rearrangement of the enol esters to the compounds of formulas (la)-(e) is conveniently carried out in a solvent at 20-40 ° C., or in the presence of an auxiliary base and with the aid of a cyano compound as catalyst. The solvent used may be, for example, acetonitrile, methylene chloride, 1,2-dichloroethane, ethyl acetate or toluene. Preferred solvent is acetonitrile. Suitable auxiliary bases are tertiary alkylamines, pyridine or alkali metal carbonates, preferably used in equimolar amounts or in excess of 4 times based on the benzoyl enol ester. Preferred auxiliary bases are two times triethylamine. Suitable catalysts are potassium cyanide, acetone cyanohydrin and trimethylsilyl cyanide, preferably used in amounts of 1 to 50 mole percent, based on the enol ester. Preferably, acetone cyanohydrin is used, for example in amounts of 5 to 15 mol%, in particular 10 mol%. Examples of rearrangements of cyanide-catalyzed, enol esters are described, for example, in EP-A 186,118 or US 4,780,127. Finishing is carried out by conventional methods, for example by acidifying the reaction mixture with a dilute inorganic acid such as hydrochloric acid or sulfuric acid at a concentration of 5% and extracting with an organic solvent such as methylene chloride or ethyl acetate. For purification, the extract is extracted with a cooled 5-10% concentration of alkali metal carbonate solution and the final product is passed through an aqueous phase. By acidifying the aqueous solution, the products of formulas (la)-(e) are precipitated with methylene chloride or ethyl acetate or extracted again and dried before the solvent is removed. 1,3-diketones of formula (II) used as starting materials are known compounds and can be prepared by methods known per se, for example, EP-A 71707, EP-A 142741, EP-A 243313. , US 4,249,937 and WO 92/13821. Cyclohexanedione and dimedone are commercially available compounds. Benzoic acid of formula III can be prepared as follows: For example, benzoyl halides such as benzoyl chloride of formula III (T = Cl) are prepared by known methods, ie by reacting benzoic acid of formula III (T = OH) with thionyl chloride. Benzoic acids of formula III (T = OH) can be prepared by known methods by acid or base hydrolysis of the corresponding esters of formula III (T = C 1 -C 4 -alkoxy). Intermediates of formula III are known in some cases or may be prepared by methods known in the literature. <Scheme 2> Thereafter, for example, the alkylthio compound IV shown in Scheme 2 is described in J. Med. Chem. Substituted haloalkenyl, such as described in 1984, 27, 1516, J. Org. Chem. 1980, 45, 4611 or J. Am. Chem. Soc. Alkynylcarboxylic acids as described in 1983, 105, 883, Chem. Ber. 1925, 58, 1612 can be reacted with a haloalkylcarboxylic acid in the presence of a base such as an alkali metal hydroxide, an alkali metal hydrate or an alkali metal carbonate. Can. J. Chem. 1981, 59, 199; Chem. Ber. 1925, 58, 1612; Chem. Ber. 1926, 59, 1072; Phosp. And Sulf. 1984, 19, 31, the resulting compound V is cyclized by addition of Lewis or protic acid under Friedel-Crafts conditions. Preferred Lewis acids are AlCl 3 or SnCl 4 , and preferred protic acids are polyphosphoric acid and sulfuric acid. Thiochromenoic acid is described, for example, in Ann. Chem. 1964, 680, 40, further by reacting a substituted thiophenolic acid with a substituted α-alkylacetic acid ester in the presence of phosphorus pentoxide, or by removing hydrogen halide from, for example, 3-halothiochromanoic acid. It can be prepared as. Alkylthio compound IV can be obtained, for example, by the Sandmeyer reaction from the corresponding aniline, and described in Organanicum. 19th Edition 1992, 552 ff, some of them are synthesized by reduction of the appropriate nitro compound. For example, if X is (-CR 12 R 13- ) or (-CR 12 R 13 CR 21 R 22- ), Y is C = O and T is C 1 -C 4 -alkoxy, The thioclomonone esters or dihydrobenzothiophene esters described can be prepared by alkylation of alkylthio compound IV in the presence of one of the bases mentioned above in solvent or water and cyclized to compound VI. In this case, the reactants and the base are used in equimolar amounts for convenience. The reaction mixture is preferably stirred at 20 to 100 ° C, in particular at 20 to 40 ° C. The finishing treatment can, for example, pour the reaction mixture into water, make the aqueous phase acidic with an inorganic acid such as hydrochloric acid or sulfuric acid, filter the useful product by suction or extract with methylene chloride or ethyl acetate, and then extract the extract. Is carried out in such a way as to dry and remove the solvent. The ester can be reacted without further purification. For example, carboxylic acids are activated by stirring compound V in polyphosphoric acid at 40-140 ° C., in particular 70-100 ° C., or via conversion to acid chloride, and Lewis acids such as AlCl 3 or SnCl 4 in the solvent. By adding 2 to 6, in particular 3.5 to 4.5 molar equivalents, or stirring in sulfuric acid, the intermediate of formula III is filtered in a known manner, ie by adding ice water and inhaling the useful product by inhalation or by ethyl acetate or methylene chloride It is obtained by finishing the process in such a manner that the aqueous phase is extracted, dried and the solvent is removed. For example, when X is an ethylene group (-CR 12 = CR 13- ), Y is C═O and T is C 1 -C 4 -alkoxy, the thioclomonone ester may be, for example, an arylthio compound. It can be converted by reacting with an acetylenecarboxylic acid derivative in water or solvent at 0 to 140 ° C. The finishing treatment can be carried out in a manner known per se, for example by adding dilute inorganic acids such as water and hydrochloric acid. The useful product is obtained by filtration by suction, extraction with methylene chloride or ethyl acetate, followed by drying and removal of the solvent. Intermediates of formula (III) can be prepared by reactions known in the literature, for example in Jerry March, Advanced Organic Chemistry, Fourth Ed., Eg. p. 910ff, the reduction reaction described in Jerry March, Advanced Organic Chemistry, Fourth Ed., Eg. 934, 935, 1039, 1226, 405ff, conversion to imines and amines as described in Jerry March, Advanced Organic Chemistry, Fourth Ed., Jerry March, Advanced Organic Chemistry, Fourth Ed. Further functionalization may be achieved by ketalization, alkylation, halogenation, removal reactions, or oxidation reactions described in. The acid of 3-alkoxy-1,2-benzisothiazole-1,1-dioxide or the acid of 3-alkoxy-1,2-benzisothiazole is derived from the corresponding saccharin derivative or 1,2-benzisothiazole. Starting, if appropriate, it can be obtained by reacting with PCl 5 , POCl 3 or chlorine and an alcohol in the presence of an auxiliary base such as triethylamine, see for example US Pat. No. 4,571,429, Arch. Pharm. 1984, 317, 807, US 4,461,901, US 450,916, J. Med. Chem. 1986, 29, 359. Saccharincarboxylic acid is described in Ann. Chem. 427, 231, 1922, Chem. Ber. 13, 1554, 1980, Chem. Ber. 25, 1740, 1892, German Offenlegungsschrift 3607343, German Patant Application P44 27 995,7. Benzo-1,4-oxaphosphate derivatives are, in some cases, described, for example, in J. Pat. Org. Chem, 1968, 33, 456 or are described, for example, in Chem. Comm. 1975, 451, J. Org. Chem, 1974, 39, 1881, J. Am. Chem. Soc. 1954, 76, 1068, by reaction from the corresponding phenol derivatives, or for example in J. Chem. Het. Chem. 1983, 20, 867 can be synthesized by combining a reaction of the halogen-substituted thiophenol derivatives and secondary reactions such as oxidation, reduction or addition. The benzoic acid of formula III can also be obtained by reacting the corresponding bromo- or iodine-substituted compound of formula VII with carbon monoxide and water in the presence of a palladium, nickel, cobalt or rhodium transition metal catalyst and base at elevated temperatures. <Scheme 3> Y is OH, C 1 -C 4 -alkoxy, Y, L, M and X have the meanings defined above. The catalyst nickel, cobalt, rhodium and especially palladium can be in the form of metals or in the form of conventional salts, for example halogen compounds such as PdCl 2 , RhCl 3 .H 2 O, acetates such as Pd (OAc) 2 , cyanide and the like. It may exist in known valence form. Metal complexes with tertiary phosphines, metal alkylcarbonyls, metal carbonyls such as CO 2 (CO) 8 , Ni (CO) 4 , tertiary phosphines such as (PPh 3 ) 2 Ni (CO) 2 There may further be transition metal salts associated with metal carbonyl complexes or tertiary phosphines. Particular preference is given to the examples mentioned last in the case of palladium as catalyst. The nature of phosphine ligands is very variable. For example, they can be represented by the formula: In the above formula n is 1, 2, 3 or 4, and R 24 to R 27 radicals are low molecular weight alkyl, such as C 1 -C 6 -alkyl, aryl, C 1 -C 4 -alkylaryl, for example benzyl, phenethyl Or aryloxy. Aryl is, for example, naphthyl, anthryl and preferably unsubstituted or substituted phenyl, with regard to their inactivation to capoxylation for substituents, otherwise they vary so widely that all inert C-organic Radicals such as C 1 -C 6 -alkyl radicals such as methyl, carbonyl radicals such as COOH, COOM, where M is for example an alkali metal, alkaline earth metal or aluminum salt, C 1 -C 6 -alkoxy radicals, or C-organic radicals bonded via oxygen. The phosphine complexes can be prepared in a manner known per se, for example as described in the literature mentioned at the beginning of this specification. For example, starting materials used are commercially available metal salts such as PdCl 2 or Pd (OCOCH 3 ) 2 , for example P (C 6 H 5 ) 3 , P (nC 4 H 9 ) 3 , There are also phosphines such as PCH 3 (C 6 H 5 ) 3 , 1,2-bis (diphenylphosphino) ethane. The amount of phosphine is usually from 0 to 20 molar equivalents, in particular from 0.1 to 10 molar equivalents, particularly preferably from 1 to 5 molar equivalents, based on the transition metal. The amount of transition metal is not critical. Of course, due to cost concerns, rather small amounts, for example 0.1 to 10 mol%, in particular 1 to 5 mol%, based on the starting materials II or III are used. The reaction for the preparation of benzoic acid III (T = OH) is carried out by adding carbon monoxide and a minimum molar equivalent of water based on the starting material VI. Water, which is a reaction component, can also be used simultaneously as a solvent, the maximum amount being not important. However, depending on the starting materials and catalysts used, it may also be advantageous to use another inert solvent or base used for carboxylation as a solvent in place of the reaction components. Suitable inert solvents are conventional solvents in the carboxylation reaction, for example hydrocarbons such as toluene, xylene, hexane, pentane, cyclopentane, for example ethers such as methyl tert-butyl ether, tetrahydrofuran, dioxane , Substituted amides such as dimethoxyethane, dimethylformamide, oversubstituted ureas such as tetra-C 1 -C 4 -alkyl-urea, or nitriles such as benzonitrile or acetonitrile. In a preferred embodiment of the process, one of the reaction components, in particular the base, is used in excess so that no additional solvent is required. Suitable bases for the process are all inert bases capable of binding the hydrogen iodide or hydrogen bromide produced during the reaction. Examples that may be mentioned herein include tertiary amines such as tert-alkylamines, trialkylamines such as triethylamine, cyclic amines such as N-methylpiperidine or N, N'-dimethylpiperazine, pyridine , Alkali metal carbonates or hydrogen carbonates, or alkyl-substituted urea derivatives such as terra-C 1 -C 4 -alkylurea tetra, for example tetramethylurea. The amount of base is not critical and usually 1 to 10 moles, in particular 1 to 5 moles, are used. If the bases are used simultaneously as solvents, the amount is generally proportional to the dissolution of the reaction components, and in order to reduce practical reasons and costs and to ensure maximum contact of the reaction components using a small reaction vessel, an unnecessary amount is required. Excess should be avoided. During the reaction, the carbon monoxide pressure is adjusted so that excess CO is always present based on compound VI. Preferably, the carbon monoxide pressure at room temperature is 1 to 250 bar, in particular 5 to 150 bar. Carbonylation is usually carried out continuously or batchwise at 20 to 250 ° C, in particular 30 to 150 ° C. For batch processes, carbon monoxide is continuously injected into the reaction mixture for convenience to maintain a constant pressure. The arylhalogen compounds VII used as starting materials are known or can be easily prepared by combining the known synthesis methods with suitable reaction sequences described above. For the intended use of the benzoyl derivatives of formula I, suitable substituents are as follows: L and M are hydrogen, C 1 -C 6 -alkyl, for example methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2 -Methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1-methylpentyl, 2-methylpentyl, 3-methyl Pentyl, 4-methylpentyl, 1,1-dimethylpentyl, 1,2-dimethylpentyl, 1,3-dimethylpentyl, 2,2-dimethylpentyl, 2,3-dimethylpentyl, 3,3-dimethylpentyl, 1 Ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl or 1-ethyl-2-methylpropyl, Especially methyl, ethyl, 1-methylethyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl and 1,1-dimethylpropyl; C 2 -C 6 -alkenyl, for example 2-propenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-pentenyl , 3-pentenyl, 4-pentenyl, 3-methyl-2-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl -4-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-2-propenyl, 2-hexenyl , 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-phene Tenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl -4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2- Dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl , 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2- Phenyl, 1-ethyl-1-methyl-2-propyl and ethyl-2-methyl-2-propenyl, In particular 1-methyl-2-propenyl, 1-methyl-2-butenyl, 1,1-dimethyl-2-propenyl and 1,1-dimethyl-2-butenyl; C 2 -C 6 -alkynyl, for example propargyl, 2-butynyl, 3-butynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-3-butynyl , 2-methyl-3-butynyl, 1-methyl-2-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 2-hexynyl, 3-hexynyl, 4 -Hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 3-methyl-4-pentynyl, 4-methyl-2 -Pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-2-butynyl, 2,2-dimethyl-3-butynyl, 1- Ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl; C 1 -C 4 -alkoxy such as methoxy, ethoxy, n-propoxy, 1-methylethoxy, n-butoxy, 1-methylpropoxy, 2-methylpropoxy and 1,1- Dimethyl epoxy, In particular, C 1 -C 3 -alkoxy, for example methoxy, ethoxy or I-propoxy, These groups can here be unsubstituted or substituted with fluorine, chlorine, bromine and iodine, preferably 1 to 5 halogen atoms such as fluorine and chlorine, or the abovementioned C 1 -C 4 -alkoxy. The-(A) m -S (O) n R 1 group defined above is for example C 1 -C 4 -alkylthio, for example methylthio, ethylthio, n-propylthio, 1-methylethylthio, n-butylthio, 1-methylpropylthio, 2-methylpropylthio and 1,1 Dimethylethylthio, in particular methylthio; C 1 -C 4 -alkylsulfinyl, for example methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, 1-methylethylsulfinyl, n-butylsulfinyl, 1-methylpropylsulfinyl, 2- Methylpropylsulfinyl and 1,1-dimethylethylsulfinyl, in particular methylsulfinyl; C 1 -C 4 -alkylsulfonyl, for example methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, 1-methylethylsulfonyl, n-butylsulfonyl, 1-methylpropylsulfonyl, 2- Methylpropylsulfonyl and 1,1-dimethylethylsulfonyl, in particular methylsulfonyl; C 1 -C 4 -alkoxysulfonyl, for example methoxysulfonyl, ethoxysulfonyl, n-propoxysulfonyl, 1-methylethoxysulfonyl, n-butoxysulfonyl, 1-methylpropoxysulfonyl , 2-methylpropoxysulfonyl and 1,1-dimethylethoxysulfonyl, in particular methoxysulfonyl; NC 1 -C 4 -alkylsulfamoyl, for example N-methylsulfamoyl, N-ethylsulfamoyl, Nn-propylsulfamoyl, N-1-methylethylsulfamoyl, Nn-butylsulfamoyl, N-1 -Methylpropylsulfamoyl, N-2-methylpropylsulfamoyl and N-1,1-dimethylethylsulfamoyl, in particular N-methylsulfamoyl; NC 1 -C 4 -alkylsulfinamoyl, for example N-methylsulfinamoyl, N-ethylsulfinayl, Nn-propylsulfinayl, N-1-methylethylsulfinayl, Nn-butylsulul Pinamoyl, N-1-methylpropylsulfinamoyl, N-2-methylpropylsulfinamoyl and N-1,1-dimethylethylsulfinamoyl, in particular N-methylsulfinamoyl; Di-C 1 -C 4 -alkylsulfamoyl, for example dimethylsulfamoyl, diethylsulfamoyl, dipropylsulfamoyl, dibutylsulfamoyl, N-methyl-N-ethylsulfamoyl, N-methyl-N -Propylsulfamoyl, N-methyl-N-1-methylethylsulfamoyl, N-methyl-N-1,1-dimethylethylsulfamoyl, di-1-methylethylsulfamoyl, N-ethyl-N-1- Methylethylsulfamoyl and N-ethyl-N-1,1-dimethylethylsulfamoyl, in particular dimethylsulfamoyl; Di-C 1 -C 4 -alkylsulfinamoyl, for example dimethylsulfinamoyl, diethylsulfinayl, dipropylsulfinamoyl, dibutylsulfinamoyl, N-methyl-N-ethylsulfinamoyl , N-methyl-N-propylsulfinamoyl, N-methyl-N-1-methylethylsulfinamoyl, N-methyl-N-1,1-dimethylethylsulfinamoyl, di-1-methylethylsulfina Moyl, N-ethyl-N-1-methylethylsulfinamoyl and N-ethyl-N-1,1-dimethylethylsulfinamoyl, especially dimethylsulfinamoyl; C 1 -C 4 -alkylsulfinyloxy, for example methylsulfinyloxy, ethylsulfinyloxy, n-propylsulfinyloxy, 1-methylethylsulfinyloxy, n-butylsulfinyloxy, 1-methyl Propylsulfinyloxy, 2-methylpropylsulfinyloxy and 1,1-dimethylethylsulfinyloxy, especially methylsulfinyloxy; C 1 -C 4 -alkylsulfonyloxy, for example methylsulfonyloxy, ethylsulfonyloxy, n-propylsulfonyloxy, 1-methylethylsulfonyloxy, n-butylsulfonyloxy, 1-methyl Propylsulfonyloxy, 2-methylpropylsulfonyloxy and 1,1-dimethylethylsulfonyloxy, especially methylsulfonyloxy; C 1 -C 4 -alkylsulfinylamino, for example methylsulfinylamino, ethylsulfinylamino, n-propylsulfinylamino, 1-methylethylsulfinylamino, n-butylsulfinylamino, 1-methyl Propylsulfinylamino, 2-methylpropylsulfinylamino and 1,1-dimethylethylsulfinylamino, especially methylsulfinylamino; C 1 -C 4 -alkylsulfonylamino, for example methylsulfonylamino, ethylsulfonylamino, n-propylsulfonylamino, 1-methylethylsulfonylamino, n-butylsulfonylamino, 1-methyl Propylsulfonylamino, 2-methylpropylsulfonylamino and 1,1-dimethylethylsulfonylamino, especially methylsulfonylamino; NC 1 -C 4 -alkylsulfinyl-N-methylamino, for example N-methylsulfinyl-N-methylamino, N-ethylsulfinyl-N-methylamino, Nn-propylsulfinyl-N-methyl Amino, N-1-methylethylsulfinyl-N-methylamino, Nn-butylsulfinyl-N-methylamino, N-1-methylpropylsulfinyl-N-methylamino, N-2-methylpropylsulfinyl- N-methylamino and N-1,1-dimethylethylsulfinyl-N-methylamino, in particular N-methylsulfinyl-N-methylamino; NC 1 -C 4 -alkylsulfinyl-N-ethylamino, for example N-methylsulfinyl-N-ethylamino, N-ethylsulfinyl-N-ethylamino, Nn-propylsulfinyl-N-ethyl Amino, N-1-methylethylsulfinyl-N-ethylamino, Nn-butylsulfinyl-N-ethylamino, N-1-methylpropylsulfinyl-N-ethylamino, N-2-methylpropylsulfinyl- N-ethylamino and N-1,1-dimethylethylsulfinyl-N-ethylamino, in particular N-methylsulfinyl-N-ethylamino; NC 1 -C 4 -alkylsulfonyl-N-methylamino, for example N-methylsulfonyl-N-methylamino, N-ethylsulfonyl-N-methylamino, Nn-propylsulfonyl-N-methyl Amino, N-1-methylethylsulfonyl-N-methylamino, Nn-butylsulfonyl-N-methylamino, N-1-methylpropylsulfonyl-N-methylamino, N-2-methylpropylsulfonyl- N-methylamino and N-1,1-dimethylethylsulfonyl-N-methylamino, in particular N-methylsulfonyl-N-methylamino; NC 1 -C 4 -alkylsulfonyl-N-ethylamino, for example N-methylsulfonyl-N-ethylamino, N-ethylsulfonyl-N-ethylamino, Nn-propylsulfonyl-N-ethyl Amino, N-1-methylethylsulfonyl-N-ethylamino, Nn-butylsulfonyl-N-ethylamino, N-1-methylpropylsulfonyl-N-ethylamino, N-2-methylpropylsulfonyl- N-ethylamino and N-1,1-dimethylethylsulfonyl-N-ethylamino, in particular N-methylsulfonyl-N-ethylamino; C 1 -C 4 -haloalkylthio, for example chloromethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio, Chlorodifluoromethylthio, 1-fluoroethylthio, 2-fluoroethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2-chloro-2,2 -Difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, 2,2,2-trichloroethylthio and pentafluoroethylthio, in particular trifluoromethylthio. The-(A) m -CO-R 2 group defined above is, for example, C 1 -C 4 -alkylcarbonyl, for example methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, 1-methylethylcarbonyl, n-butylcarbonyl, 1-methylpropylcarbonyl, 2- Methylpropylcarbonyl and 1,1-dimethylethylcarbonyl, especially methylcarbonyl; C 1 -C 4 -alkoxycarbonyl, for example methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, 1-methylethoxycarbonyl, n-butoxycarbonyl, 1-methylprop Foxoxycarbonyl, 2-methylpropoxycarbonyl and 1,1-dimethylepoxycarbonyl, in particular methoxycarbonyl; NC 1 -C 4 -alkylcarbamoyl, for example N-methylcarbamoyl, N-ethylcarbamoyl, Nn-propylcarbamoyl, N-1-methylethylcarbamoyl, Nn-butylcarba Barmoyl, N-1-methylpropylcarbamoyl, N-2-methylpropylcarbamoyl and N-1,1-dimethylethylcarbamoyl, in particular N-methylcarbamoyl; Di-C 1 -C 4 -alkylcarbamoyl, for example dimethylcarbamoyl, diethylcarbamoyl, dipropylcarbamoyl, dibutylcarbamoyl, N-methyl-N-ethylcarbamoyl , N-methyl-N-propylcarbamoyl, N-methyl-N-1-methylethylcarbamoyl, N-methyl-N-1,1-dimethylethylcarbamoyl, di-1-methylethylcarba Moyl, N-ethyl-N-1-methylethylcarbamoyl and N-ethyl-N-1,1-dimethylethylcarbamoyl, in particular dimethylcarbamoyl; C 1 -C 4 -alkylcarbonyloxy, for example methylcarbonyloxy, ethylcarbonyloxy, n-propylcarbonyloxy, 1-methylethylcarbonyloxy, n-butylcarbonyloxy, 1-methyl Propylcarbonyloxy, 2-methylpropylcarbonyloxy and 1,1-dimethylethylcarbonyloxy, especially methylcarbonyloxy; C 1 -C 4 -alkylcarbonylamino, for example methylcarbonylamino, ethylcarbonylamino, n-propylcarbonylamino, 1-methylethylcarbonylamino, n-butylcarbonylamino, 1-methyl Propylcarbonylamino, 2-methylpropylcarbonylamino and 1,1-dimethylethylcarbonylamino, especially methylcarbonylamino; NC 1 -C 4 -alkylcarbonyl-N-methylamino, for example N-methylcarbonyl-N-methylamino, N-ethylcarbonyl-N-methylamino, Nn-propylcarbonyl-N-methyl Amino, N-1-methylethylcarbonyl-N-methylamino, Nn-butylcarbonyl-N-methylamino, N-1-methylpropylcarbonyl-N-methylamino, N-2-methylpropylcarbonyl- N-methylamino and N-1,1-dimethylethylcarbonyl-N-methylamino, in particular N-methylcarbonyl-N-methylamino. X is for example CH 2 , CH (CH 3 ), C ((CH 3 ) 2 ), CH (C 2 H 5 ), C ((C 2 H 5 ) 2 ) CH (C 6 H 5) , CH 2 -CH 2 , CH 2 -CH (CH 3 ), CH 2 -C ((CH 3 ) 2 ), CH (CH 3 ) -CH (CH 3 ), CH (CH 3 ) -C ((CH 3) ) 2 ), C ((CH 3 ) 2 ) -C ((CH 3 ) 2 ), CH 2 -CH (C 2 H 5 ), CH 2 -C ((C 2 H 5 ) 2 ), CH (C 2 H 5 ) -CH (C 2 H 5 ), CH (C 2 H 5 ) -C ((C 2 H 5 ) 2 ), C ((C 2 H 5 ) 2 ) -C ((C 2 H 5 ) 2 ), CH 2 -CH (C 3 H 7 ), CH 2 -CH (iC 3 H 7 ), CH 2 -CH (C 4 H 9 ), CH 2 -CH (iC 4 H 9 ), CH 2 -CH (Br), CH 2 -C ((Br) 2 ), CH (Br) -CH (Br), CH ((Br) 2 ) -C ((Br) 2 ), CH 2 -CH ( Cl), CH 2 -C ((Cl) 2 ), CH (Cl) -CH ((Cl) 2 ), CH ((Cl) 2 ) -C ((Cl) 2 ), CH 2 -CH (C 6 H 5 ), CH (C 6 H 5 ) -CH (C 6 H 5 ), CH 2 -CH (p-NO 2 C 6 H 5 ), CH = CH, C (CH 3 ) = CH, C (CH 3 ) = CCH 3 , CH = CBr, CH = CCl, CBr = CBr, CCl = CCl, CH = C (OCH 3 ), CH = C (C 5 H 6 ), C (C 5 H 6 ) = C (C 5 H 6 ), C (C 2 H 5 ) = CH, C (C 2 H 5 ) = C (C 2 H 5 ), CH = C (C 3 H 5 ), CH = C (C 4 H 7 ), CH 2 -CH = CH, CH (CH 3 ) -CH = CH, CH (( CH 3 ) 2 ) -CH = CH, CH 2 -CH = C (CH 3 ), CH 2 -C (CH 3 ) = CH, CH 2 -C (CH 3 ) = C (CH 3 ), CH (CH 3 ) -C (CH 3 ) = C (CH 3 ), C ((CH 3 ) 2 ) -C (CH 3 ) = C (CH 3 ), NH, N-CH 3 , NC 2 H 5 , NC 3 H 7 , NC 4 H 9 , N-iC 3 H 7 , N-OCH 3 , N-OC 2 H 5 , N-CH 2 C 6 H 5 , NC 6 H 5 . Y is for example C = O, CH-OH, CH-OCH 3 , CH-OC 2 H 5 , CH-OC 3 H 7 , CH-OPr, CH-OC 4 H 9 , CH-OiBu, CH- OC 5 H 11 , CH-OC 6 H 13 , C (CH 3 ) -OCH 3 , C (CH 3 ) -OC 2 H 5 , C (CH 3 ) -OC 2 H 5 , C (CH 3 ) -OC 3 H 7 , C (CH 3 ) -OC 4 H 9 , C (CH 3 ) -OiPr, C (CH 3 ) -OiBu, C (CH 3 ) -OPh, CH 2 , CH (CH 3 ), C ( (CH 3 ) 2 ), C = NC 2 H 5 , C = NC 3 H 7 , C = NC 4 H 9 , C = N-iC 4 H 9 , C = N-tC 4 H 9 , C = N- iPr, C = N-OCH 3 , C = N-OC 2 H 5 , C = N-OC 3 H 7 , C = N-OC 4 H 9 , C = N-OiC 4 H 9 , C = N-OtC 4 H 9 , C = N-OCH 2 CH = CH 2 , C = N-OCH (CH 3 ) CH = CH 2 , C = N-OCH 2 CH = CHCH 3 , C = N-OCH 2 CH = C ( CH 3 ) 2 , C = N-OCH 2 CH = CHBr, C = N-OCH 2 CH = CHCl, C = N-OCH 2 CH = CHC 2 H 5 , C = N-OCH 2 C≡CH, C = N-OCH 2 C≡CCH 3 , C = N-OCH 2 C 6 H 5 , C = N-OCH 2 C 6 H 5 , CH-NH (OCH 3 ), CH-NH (OC 2 H 5 ), CH -NH (OiPr), CH-NH (OnPr), CH-NH (OC 6 H 5 ), CH-N (CH 3 ) 2 , CH-NCH 3 (OC 2 H 5 ), CH-NCH 3 (OiPr) , CH-NCH 3 (OnPr), CH-NCH 3 (OC 6 H 5 ), CH-NH (CH 3 ), CH-NH (C 2 H 5 ), CH-NH (C 3 H 7 ), CH- NH (C 4 H 9 ), CH-NH (iPr), CH-NH (iBu), CH-NH (tBu), CH-NH (C 6 H 5 ), CH- N (CH 3 ) 2 , CH-NCH 3 (C 2 H 5 ), CH-NCH 3 (C 3 H 7 ), CH-NCH 3 (C 4 H 9 ), CH-NCH 3 (iPr), CH- NCH 3 (iBu), C = N-NH 2 , C = N-NHCH 3 , C = NN ((CH 3 ) 2 ), C = N-NH (C 2 H 5 ), C = N-NCH 3 ( C 2 H 5 ), C = NN ((C 2 H 5 ) 2 ), CH-SCH 3 , CH-SC 2 H 5 , CH-SC 3 H 7 , CH-SC 4 H 9 , CH-SPr, CH -SiBu, CH-SH, C (CH 3 ) -SCH 3 , C (CH 3 ) -SC 2 H 5 , C (CH 3 ) -SC 3 H 7 , 1,3-dioxanyl, 1,3- Dioxolanyl, 5,5-dimethyl-1,3-dioxanyl. Preferred benzoyl derivatives are compounds of formula (Ia). Where L is hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1- C 4 -haloalkyl, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkylthio, C 1 -C 4 -alkylsulfonyl, halogen, nitro or cyano, M is hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1- C 4 -haloalkyl, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkylthio, C 1 -C 4 -alkylsulfonyl, halogen, nitro or cyano, Q, X, n and Y have the meanings defined for Compound I above, When Y = C = O, X is not NR 23 . Preferred benzoyl derivatives are also compounds of formula Ib. Where L is C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl, C 1 -C 4 Haloalkoxy, halogen, nitro or cyano, M is hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl, C 1- C 4 -haloalkoxy, halogen, nitro or cyano, Q, X, n and Y have the meanings defined for Compound I above, When Y = C = O, X is not NR 23 . Preferred benzoyl derivatives are also compounds of formula I, wherein the L and M radicals are hydrogen, methyl, methoxy, chlorine, cyano, nitro or trifluoromethyl. Preferred benzoyl derivatives are compounds of formula (Ic). Where L is hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl, C 1- C 4 -haloalkoxy, halogen, nitro or cyano, M is hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl, C 1- C 4 -haloalkoxy, halogen, nitro or cyano, Q, n, Y and R 21 , R 22 , R 12 and R 13 have the meanings defined for compound I above. Likewise, preferred benzoyl derivatives are compounds of formula Id. Where L is hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl, C 1- C 4 -haloalkoxy, halogen, nitro or cyano, M is hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl, C 1- C 4 -haloalkoxy, halogen, nitro or cyano, Q, n, Y and R 12 and R 13 have the meanings defined for compound I above. Preferred benzoyl derivatives are also compounds of formula (Ie). Where L is hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl, C 1- C 4 -haloalkoxy, halogen, nitro or cyano, M is hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl, C 1- C 4 -haloalkoxy, halogen, nitro or cyano, Q, n, Y, R 12 and R 13 have the meanings defined for Compound I above. Preferred benzoyl derivatives are also compounds of formula I wherein n is 1 or 2 and Y is CR 7 -OR 8 , wherein R 7 and R 8 have the meanings defined for compound I above. The R 12 radicals of X and the R 7 radicals of Y form a bond. The R 12 radicals of X and the R 7 radicals of Y form a bond. R 7 and R 23 radicals form a bond. <Production example> A) Preparation of Starting Materials and Intermediates 1.3-thio-2-methylbenzoic acid 100 g (0.66 mol) of 3-amino-2-methylbenzoic acid were first charged with 270 g of ice and 127 ml of concentrated hydrochloric acid. Then 45.7 g (0.66 mol) of sodium nitrite in 270 ml of water were added dropwise at 0 to 10 ° C. In a second vessel 84.2 g (0.79 mole) of sodium carbonate and 106 g (0.66 mole) of potassium methylxanthate were dissolved in 450 ml of water and heated to 60-70 ° C. Diazonium solution was carefully added dropwise. Subsequently, the mixture was stirred for 1 hour. 106 g (2.65 mol) of sodium hydroxide in 270 ml of water were added and the mixture was stirred for 2 hours, then the solution was acidified with hydrochloric acid and the resulting precipitate was filtered off with suction. The solid was washed with water and dried. Yield: 110 g of 3-thio-2-methylbenzoic acid (100% of theory); Melting point 155 ° C .; 1 H-NMR (δ 6 -DMSO): δ [pm] = 13.0 (1H, bs), 7.7 (2H, m), 7.3 (1H, tr), 2.4 (3H, s). 2. Methyl 3-thio-2-methylbenzoate 100 g (0.66 mol) of 3-amino-2-methylbenzoic acid were dissolved in 1.6 l of methanol containing 5% sulfuric acid and the mixture was refluxed for 5 hours. Thereafter, the alcohol was distilled off, the residue was dissolved in ethyl acetate, and the organic phase was washed with water and sodium carbonate, then dried over sodium sulfate and concentrated. Yield: 104 g of methyl 3-thio-2-methylbenzoate (87% of theory); 1 H-NMR (CDCl 3 ): δ [pm] = 7.6 (1H, d), 7.4 (1H, d), 7.1 (1H, d), 3.9 (3H, s), 3.4 (1H, s), 2.5 (3H, s). 3. Methyl 3-thio (2'-propionic acid) -2-methylbenzoate 70 g (0.38 mol) of methyl 3-thio-2-methylbenzoate were dissolved in 400 ml of water and refluxed with 30.8 g (0.77 mol) of sodium hydroxide solution and 58.8 g (0.45 mol) of bromopropionic acid for 7 hours. After cooling, the aqueous phase was washed with methyl tert-butyl ether. The aqueous phase was then acidified with 2N hydrochloric acid, and the resulting precipitate was filtered off with suction and washed with water and the product dried. Yield: 75.5 g of methyl 3-thiopropionic acid-2-methylbenzoate (78% of theory); 1 H-NMR (CDCl 3 ): δ [pm] = 7.66 (1H, d), 7.51 (1H, d), 7.20 (1H, tr), 3.96 (3H, s), 3.18 (2H, tr), 2.70 (2H, tr), 2.63 (3H, s). 4. Methyl 8-methylthiochroman-4-one-7-carboxylate 4 g (15.8 mmol) of methyl 3-thiopropionic acid-2-methylbenzoate were stirred in 40 g of polyphosphoric acid at 70 ° C. for 15 minutes. Thereafter, the reaction solution was added to ice water and the resulting precipitate was suction filtered. The product was washed with water and dried in a drying room. As a byproduct of the cyclization reaction, methyl 8-methylthiochroman-4-one-7-carboxylate is produced, which can be separated by chromatography. Yield: 3.1 g of methyl 8-methylthiochroman-4-one-7-carboxylate (83% of theory); 1 H-NMR (CDCl 3 ): δ [pm] = 8.00 (1H, d), 7.30 (1H, d), 3.94 (3H, s), 3.15 (2H, m), 2.98 (2H, m), 2.50 (3H, s); Second component: methyl 8-methylthiochroman-4-one-7-carboxylate: 1 H-NMR (CDCl 3 ): δ [pm] = 8.4 (1H, d), 7.9 (1H, d), 7.8 (1H, d), 7.0 (1H, d), 4.0 (3H, s), 2.7 (3H, s). 5. 8-Methylthiochroman-4-one-7-carboxylic acid 41.1 g (0.17 mol) of methyl 8-methylthiochroman-4-one-7-carboxylate were hydrolyzed under reflux with 10.3 g (0.26 mol) of NaOH in 400 ml of a mixture of water and methanol. Thereafter, methanol was distilled off and the residue was diluted with water and acidified with 2N hydrochloric acid. The useful product precipitated out, filtered off with suction, washed with water and dried. Yield: 34.4 g of 8-methylthiochroman-4-one-7-carboxylic acid (89% of theory); Melting point: 243 to 246 ° C. 6. 8-Methyl-1,1-dioxothiochroman-4-one-7-carboxylic acid 20 g (0.09 mol) of 8-methylthiochroman-4-one-7-carboxylic acid was dissolved in 100 ml of acetic acid. A small amount of sodium tungstate was added. Thereafter, 24.9 g (0.22 mol) of a 30% strength hydrogen peroxide solution was added dropwise at 50 ° C. The mixture was then stirred at about 20 ° C for 1 hour. Then the reaction solution was added to water and the precipitate was suction filtered. The product was washed with water and then dried. Yield: 18.4 g of 8-methyl-1,1-dioxothiochroman-4-one-7-carboxylic acid (80% of theory); melting point: 224 to 225 ° C. 7. Methyl 4-hydroxy-8-methylthiochroman-7-carboxylate 30 g (0.127 mol) of methyl-8-methylthiochroman-4-one-7-carboxylate were dissolved in a mixture of 120 ml of methylene chloride and 60 ml of methanol and cooled to 0-5 ° C. Thereafter, 2.4 g (0.064 mol) of sodium borohydride were added all at once. The mixture was then stirred at this temperature for 1 hour and 200 ml of 2N hydrochloric acid was added to the reaction solution. Two phases were created. The organic phase was separated and dried and the solvent was removed by distillation. The crude product was reacted directly without further purification. Yield: 27.6 g of methyl 4-hydroxy-8-methylthiochroman-7-carboxylate (91% of theory). 8. Methyl 4-ethoxy-8-methylthiochroman-7-carboxylate 13.8 g (0.058 mol) of methyl-4-hydroxy-8-methylthiochroman-7-carboxylate were heated at boiling point in 60 ml of ethanol for 4 hours with the addition of 1 g of sulfuric acid. Thereafter, the solvent was distilled off and the residue was dissolved in water. The aqueous phase was extracted with ethyl acetate. The organic phase was washed with sodium hydrogen carbonate solution, dried and concentrated. The product was purified by chromatography. Yield: 10.1 g of methyl 4-ethoxy-8-methylthiochroman-7-carboxylate (60% of theory); 1 H-NMR (CDCl 3 ): δ [pm] = 7.44 (1H, d), 7.13 (1H, d), 4.40 (1H, m), 3.90 (3H, s), 3.60 (2H, m), 3.38 (1H, dtr), 2.90 (1H, m), 2.50 (3H, s), 2.40 (1H, m), 1.98 (1H, m), 1.10 (3H, tr). Reaction to produce methyl 4-methoxy-8-methylthiochroman-4-one-7-carboxylate and methyl 4-isopropoxy-8-methylthiochroman-4-one-7-carboxylate Is carried out analogously to the above process, in the case of methyl 4-methoxy-8-methylthiochroman-4-one-7-carboxylate, ethanol is replaced by methanol and methyl 4-isopropoxy-8- For methylthiochroman-4-one-7-carboxylate, ethanol was replaced with isopropanol. 9. 4-ethoxy-8-methylthiochroman-7-carboxylic acid 2.1 g of sodium hydroxide solution was dissolved in 20 ml of water. Methyl 4-ethoxy-8-methylthiochroman-4-one-7-carboxylate dissolved in 20 ml of methanol was added dropwise at about 20 ° C. The mixture was refluxed for 2 hours. Thereafter, the solvent was distilled off and the residue was added to 2N hydrochloric acid. The aqueous phase was extracted with methylene chloride and the organic phase was concentrated to dryness. Yield: 9.3 g of 4-ethoxy-8-methylthiochroman-7-carboxylic acid (100% of theory); Melting point: 89 to 98 ° C. Hydrolysis of the esters corresponding to 4-ethoxy-8-methylthiochroman-7-carboxylic acid and 4-isopropoxy-8-methylthiochroman-7-carboxylic acid is carried out in a similar manner. Using the same method, hydrolysis of the corresponding benzothiophene derivatives shown below is carried out. 10. 8-Methyl-4-ethoxy-1,1-dioxothiochroman-7-carboxylic acid 8.4 g (0.033 mol) of 4-ethoxy-8-methylthiochroman-7-carboxylic acid were first introduced into 60 ml of acetic acid. A small amount of sodium tungstate was added. Thereafter, 7.9 g (0.07 mol) of a 30% strength hydrogen peroxide solution was added dropwise at 50 ° C, and the reaction mixture was then stirred for 2 hours. Then, the reaction solution was poured into water and the aqueous phase was extracted with ethyl acetate. The organic phase was washed with bisulfite solution and concentrated to dryness. Yield: 9.5 g of 8-methyl-4-ethoxy-1,1-dioxothiochroman-7-carboxylic acid (100% of theory); Melting point: 150 ° C. 11. 8-methylthiochroman-4-one-7-carboxylic acid O-ethyl oxime 0.88 g (9 mmol) of ethylhydroxyamine was first charged in 20 ml of methanol. 0.62 g (4.5 mmol) of potassium carbonate was added followed by 2.0 g (9 mmol) of 8-methylthiochroman-4-one-7-carboxylic acid. The reaction was stirred at about 20 ° C for 10 days. Finished by addition of water and 2N hydrochloric acid, and the resulting precipitate was suction filtered and dried. Yield: 2.2 g of 8-methylthiochroman-4-one-7-carboxylic acid O-ethyl oxime (92% of theory); Melting point: 166 캜. 12. 8-Methyl-1,1-dioxothiochroman-4-one-7-carboxylic acid O-ethyl oxime 3.0 g (0.011 mol) of 8-methylthiochroman-4-one-7-carboxylic acid O-ethyl oxime was charged with a small amount of sodium tungstate in 30 ml of acetic acid. Thereafter, 2.8 g (0.024 mol) of a 30% strength hydrogen peroxide solution was added dropwise at 50 ° C. After stirring for 1 hour, the reaction mixture was poured into ice water and the resulting precipitate was suction filtered. The product was washed with water and then dried. Yield: 2.5 g of 8-methyl-1,1-dioxothiochroman-4-one-7-carboxylic acid O-ethyl oxime (74% of theory); Melting point 198 ° C. 13. 8-Methyl-1-oxothiochroman-4-one-7-carboxylic acid 7.0 g (31.5 mmol) of 8-methylthiochroman-4-one-7-carboxylic acid were charged with a small amount of sodium tungstate in 70 ml of acetic acid. 3.6 g (31.5 mmol) of 30% strength hydrogen peroxide solution were added dropwise at 50 ° C, and the reaction solution was stirred for 2 hours. Then it was stirred in water and the product was extracted with ethyl acetate. The organic phase was dried and the solvent removed. The product was purified by chromatography. Yield: 5.4 g of 8-methyl-1-oxothiochroman-4-one-7-carboxylic acid (72% of theory); 1 H-NMR (δ 6 -DMSO): δ [pm] = 8.0 (2H, m), 3.5 (3H, m), 2.8 (1H, m), 2.7 (3H, s). 14. Methyl 3-carboxymethylthio-2-methylbenzoate 12.4 g (0.068 mmol) of methyl-3-mercapto-2-methylbenzoate in 80 ml of dimethylformamide are added dropwise to 1.6 g (0.068 mol) of sodium hydride in 40 ml of dimethylformamide and the mixture is added at about 20 ° C. Stir for 60 minutes. Thereafter, 8 g (0.068 mol) of chloroacetic acid was added, and the mixture was stirred at about 20 ° C. for 4 hours. The reaction mixture was finished by pouring into iced water containing hydrochloric acid and stirring. The resulting precipitate was suction filtered, washed with water and dried. Yield: 14.6 g of methyl-3-carboxymethylthio-2-methylbenzoate (89% of theory); 1 H-NMR (δ 6 -DMSO): δ [pm] = 7.55 (1H, d), 7.45 (1H, d), 7.21 (1H, tr), 3.82 (2H, s), 2.5 (3H, s) . 15. Methyl 7-methylbenzo [b] thiophene-3 [2H] -one-6-carboxylate 14.3 g (0.06 mmol) of 3-carboxymethylthio-2-methylbenzoic acid were dissolved in 300 ml of methylene chloride and 13.1 g (0.11 mmol) of thionyl chloride was added dropwise. The mixture was refluxed for 1 hour, and then the solvent and excess thionyl chloride were distilled off. The residue was dissolved in 100 ml of methylene chloride and treated with 31.8 g (0.24 mmol) of aluminum trichloride. The reaction was stirred at about 20 ° C for 1 hour. Then the mixture was added to ice water and the organic phase was separated. After the organic phase was washed and dried, the solvent was removed. The product was further reacted without purification. Yield: 12.9 g of methyl 7-methylbenzo [b] -thiophen-3 [2H] -one-6-carboxylate (97% of theory); 1 H-NMR (CDCl 3 )): δ [pm] = 7.65 (2H, m), 3.93 (3H, s), 3.88 (2H, s), 2.50 (3H, s). 16. Methyl 7-methyl-3-hydroxybenzo [b] thiophene- [2H] -6-carboxylate 12.8 g (0.058 mol) of methyl 7-methylbenzo [b] thiophene-3 [2H] -one-6-carboxylate was dissolved in 120 ml of methylene chloride and 60 ml of methanol and cooled to 0 ° C. 1.1 g (0.029 mol) of sodium borohydride were added all at once and the mixture was stirred for 3 hours. The reaction was terminated by adding water. The phases were separated and the aqueous phase was extracted with methylene chloride. The combined organic phases were dried and the solvent was distilled off. The crude product was further reacted. Yield: 13.2 g of methyl 7-methyl-3-hydroxybenzo [b] -thiophene- [2H] -6-carboxylate (100% of theory); 1 H-NMR (CDCl 3 )): δ [pm] = 7.6 (2H, d), 5.3 (1H, m), 3.9 (3H, s), 3.7 (1H, m), 3.3 (1H, m), 2.4 (3H, s). 17. Methyl 7-methyl-3-hydroxybenzo [b] thiophene- [2H] -6-carboxylate 2.4 g (0.059 mol) of NaH were dissolved in 50 mL of dimethyl formamide. 13.2 g of methyl 7-methyl-3-hydroxybenzo [b] thiophene- [2H] -6-carboxylate in 50 mL of dimethyl formamide was added dropwise and the mixture was stirred at 20 ° C. for 2 hours. Then 8.4 g (0.059 mol) of iodomethane were added and the mixture was further stirred for 2 hours. The reaction solution was added to ice water and extracted with ethyl acetate. The organic phase is dried, concentrated and the product is purified by chromatography. Yield: 3.5 g of methyl 7-methyl-3-hydroxybenzo [b] thiophene- [2H] -6-carboxylate (25% of theory); 1 H-NMR (CDCl 3 )): δ [pm] = 7.60 (1H, d), 7.20 (1H, d), 5.04 (1H, m), 3.90 (3H, s), 3.56 (1H, m), 3.40 (3H, s), 3.38 (1H, m), 2.50 (3H, s). In addition, similar to the hydrolysis of the thiochromenone esters described above, the corresponding benzothiophenic acid can be obtained. The compounds shown in the table below are obtained in a similar manner. Preparation of Final Product 1.2- (8-Methyl-1,1-dioxothiochroman-4-one-7-carbonyl) -1,3-cyclohexanedione a) 17.4 g (0.0685 mol) of 8-methyl-1,1-dioxothiochroman-4-one-7-carboxylic acid is dissolved in 170 ml of toluene, and a drop of dimethylformamide is added, followed by thionyl 8.96 g (0.0753 mol) chloride was added. After refluxing for 4 hours, the reaction mixture was concentrated. The reaction product was further reacted directly. Yield: 8-methyl-1,1-dioxothiochroman-4-one-7-carbonyl chloride b) 0.62 g (5.5 mmol) of cyclohexane-1,3-dione were first introduced into 10 ml of acetonitrile together with 0.56 g (5.5 mol) of triethylamine. 8-methyl-1,1-dioxothiochroman-4-one-7-carbonyl chloride in 20 ml of acetonitrile was added dropwise. Subsequently, the mixture was stirred at about 2 ° C for 1 hour. Then 0.31 g (3.7 mmol) acetone cyanohydrin and 2.8 g (22.5 mmol) triethylamine were added and the mixture was stirred for 1 hour. The reaction solution was stirred in 2N hydrochloric acid for finishing treatment and the organic phase was extracted with ethyl acetate. The organic phase was then extracted with Na 2 CO 3 solution and acidified while cooling the alkaline aqueous phase. The resulting precipitate was suction filtered, washed with water and dried. Yield: 1.0 g of 2- (8-methyl-1,1-dioxothiochroman-4-one-7-carbonyl) -1,3-cyclohexanedione (52% of theory); Melting Point 173-178 ° C 2. 2- (8-Methyl-1,1-dioxothiochroman-4-one-7-carbonyl O-ethyl oxime) cyclohexane-1,3-dione 1.0 g (3.4 mmol) of 8-methyl-1,1-dioxochroman-4-one-7-carboxylic acid O-ethyl oxime with aceto with 0.39 g (3.5 mmol) of cyclohexane-1,3-dione First in 10 ml nitrile. 0.75 g (3.6 mmol) of dicyclocarbodiimide (DCC) was added and the mixture was stirred for 2 hours. 0.1 ml of acetone cyanohydrin and 0.51 g (5.1 mmol) of triethylamine were then added and the reaction mixture was further stirred for 2 hours. Thereafter, the mixture was stirred in sodium carbonate, extracted with ethyl acetate, and the organic phase was removed. The aqueous phase was acidified with hydrochloric acid and extracted again with ethyl acetate, then the organic phase was dried and the solvent was distilled off. The product was purified by chromatography. Yield: 600 mg of 2- (8-methyl-1,1-dioxothiochroman-4-one-7-carbonyl O-ethyl oxime) cyclohexane-1,3-dione (45% of theory); Melting point; 143 ° C. 3. 2- (8-Methyl-4-ethoxy-1,1-dioxothiochroman-7-carbonyl) cyclohexane-1,3-dione a) 8.8 g (0.031 mmol) of 8-methyl-4-ethoxy-1,1-dioxothiochroman-7-carboxylic acid is dissolved in 50 ml of toluene and the solution is treated with 2 drops of dimethylformamide. Then, 4.4 g (0.04 mmol) thionyl chloride was added. After refluxing for 4 hours, the reaction mixture was concentrated. Acid chloride was further used directly. b) 0.56 g of cyclohexane-1,3-dione was first introduced into 10 ml of methylene chloride together with 0.47 g (6 mmol) of pyridine. 1.5 g (5 mmol) of acid chloride from 3a) in 20 ml of methylene chloride were added dropwise and the mixture was stirred for 1 hour. The reaction solution was added to water and acidified with hydrochloric acid. The aqueous phase was extracted with ethyl acetate and the organic phase was dried and then the solvent was removed. Yield: 1.88 g of O-acylated product (99% of theory). c) 1.3 g (3.4 mmol) of the product from 3b) were dissolved in 20 ml of acetonitrile. Thereafter, 0.19 g (2.3 mmol) of acetone cyanohydrin and 1.7 g (17.2 mmol) of triethylamine were added, and the mixture was stirred for 2 hours. The organic phase was removed by washing with sodium carbonate. Finally, the alkaline aqueous phase was acidified with hydrochloric acid. The resulting precipitate was suction filtered and dried. Yield: 0.6 g of 2- (8-methyl-4-ethoxy-1,1-dioxothiochroman-7-carbonyl) cyclohexane-1,3-dione (46% of theory); 1 H-NMR (CDCl 3 ): δ [pm] = 17.5 (1H, s), 7.30 (1H, d), 7.18 (1H, d), 4.47 (1H, m), 3.95-3.83 (1H, m) , 3.70-3.50 (2H, m), 3.28 (1H, m), 2.81 (2H, tr), 2.71-2.50 (2H, m), 2.64 (3H, s), 2.43 (2H, tr), 2.05 (2H , m), 1.24 (3H, tr). The compounds shown in the following table were obtained in a similar manner: Compound I and its agriculturally available salts are suitable for herbicides in both isomeric mixtures and pure isomers. Isomer-containing preparation compositions, in particular at high rates of use, allow to perform very effective plant growth inhibition on non-crop parts. They can suppress broad-leaf weeds and grass weeds in crops such as wheat, rice, corn, soybeans, and cotton without causing significant harm to the crops. This effect is especially pronounced at low utilization rates. In view of the variety of methods of use, compound I or a composition containing it can be used in addition to more crops for removing undesirable plants. Examples of suitable crops include Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Beta vulgaris spec. ), Altissima, beta vulgaris, rapa, brassica napus var. Napus, brassica napus var. Napobrassica, brassica Brasica rapa var.silvestris, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis Citrus sinensis, Copea arabica ((Coffea canephora), Copea liberica), Cucumis sativus, Cynodon dactylon ), Daucus carota, Elaeis guineensis, Fragararia vesca, Glycine max, Gossypium hirsutum, ((Gossipium) Alboreum (Gossypium arboreum), Gossypium herbaceum, Gossypium vitifolium, Helianthus annuus, Hevea brasiliensis, Holdeum Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum Ucitaritis Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Manihot esculenta, Meticago sativa, Musa spec. Nicotiana tabacum ((Ninicoiana tabacum) Car (N. rutica)), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus Vulgaris, Picea abies , Pinus spec., Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Lives sylvestre ( Ribes sylvestre, Ricinus communis, Saccharum officinarum, Secale cereale, Solarum tuberosum, Solshum bicolor (S. vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticum durum, Visica Pava ( Vicia faba), Vitis vinifera and Zea mays. Furthermore, Compound I can be used in crops that are resistant to herbicide action as a result of breeding by genetic engineering methods. Compounds I and compositions containing them can be, for example, ready-to-use spray aqueous solutions, powders, suspensions, or high proportions of aqueous, oily or other suspensions, or dispersions, emulsions, oil dispersions, pastes, powders, spraying materials or granules. Can be used by spraying, spraying, dusting, spraying or pouring. The form of use depends on the intended use; In each case, they should be as finely dispersed as possible the active compound according to the invention. Suitable inert auxiliaries are mainly inorganic oil fractions up to the high boiling point of the medium, such as kerosene or diesel oils, and also coal tar oils and vegetable or animal derived oils, paraffin oils, tetrahydronaphthalenes, alkylated naphthalenes or derivatives thereof, alkylated Aliphatic, cyclic and aromatic hydrocarbons such as benzene and derivatives thereof, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, amines such as N-methylpyrrolidone, and strong polar solvents such as water. Aqueous use forms can be prepared by adding water from emulsion concentrates, dispersions, pastes, wettable powders or water-dispersible granules. To prepare emulsions, pastes or oil dispersions, wetting agents, tackifiers, dispersants or emulsifiers can be used to homogenize the water, as dissolved in oils or solvents. However, concentrates can be prepared containing the active ingredient, wetting agent, tackifier, dispersant or emulsifier and, if possible, a solvent or oil, which concentrate is suitable for dilution with water. Suitable surfactants (adjuvant) include alkali metal salts and alkaline earth metal salts, for example ammonium salts of alkyl sulfonic acids and fatty acids such as lignosulfonic acid, phenolsulfonic acid, naphthalenesulfonic acid and dibutylnaphthalenesulfonic acid, alkylsulfonates and alkylarylsulfonates, Alkylsulfonates, lauryl ether sulfates and fatty alcohol sulfates, and salts of sulfated hexa-, hepta- and octadecanol, and salts of fatty alcohol glycol ethers, sulfated naphthalene and derivatives thereof with formaldehyde , Condensates of naphthalene or naphthalenesulfonic acid with phenols and formaldehyde, polyoxyethylene octylphenyl ethers, ethoxylated isooctyl-, octyl- or nonylphenols, alkylphenyl polyglycol ethers, tributylphenyl polyglycol ethers , Alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohols / ethylene oxide A compound, ethoxylated castor oil, polyoxyethylene alkyl ethers or polyoxypropylene alkyl ethers, lauryl alcohol polyglycol ether acetate, sorbitol esters, lignin, sulfite waste liquid, or methylcellulose. Powders, dusting agents and powders can be prepared by mixing or grinding the active materials with a solid carrier. Granules such as coated granules, impregnated granules and homogeneous granules can be prepared by binding the active ingredients to a solid carrier. Solid carriers include inorganic earths such as silicic acid, silica gel, silicates, talc, kaolin, limestone, lime, chalk, church clay, ocher, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, pulverized synthetic materials Fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, urea and products derived from plants such as cereal flour, bark flour, wood flour and nutshell powder, cellulose powder or other solid carriers. The concentration of active compound I in ready-to-use formulations can be varied within a wide range. Usually, the formulation contains about 0.001 to 98% by weight, preferably 0.01 to 95% by weight of one or more active compounds. The active compound is used in purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum). The preparation of such products is illustrated by the following compositional example: Compound I according to the invention can be prepared, for example, as follows. I. Compound No. 13.1 20 parts by weight 80 parts by weight of alkylated benzene, 10 parts by weight of an addition of 8 to 10 moles of ethylene oxide to 1 mole of oleic acid N-monoethanolamide, 5 parts by weight of calcium dodecylbenzenesulfonate And 5 parts by weight of an adduct of 40 moles of ethylene oxide to 1 mole of castor oil. The solution was poured into 100,000 parts by weight of water and distributed well so that an aqueous dispersion containing 0.02% by weight of the active ingredient was obtained. II. Compound No. 13.3 20 parts by weight of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of an addition of 40 moles of isooctylphenol and 10 parts by weight of an addition of 40 moles of ethylene oxide to 1 mole of castor oil It dissolved in the mixture containing. The solution was poured into 100,000 parts by weight of water and allowed to disperse well to obtain an aqueous dispersion containing 0.02 wt% of the active compound. III. In a mixture comprising 25 parts by weight of cyclohexanone, 65 parts by weight of an inorganic oil fraction having a boiling point of 210 to 280 ° C. and 10 parts by weight of an addition of 40 moles of ethylene oxide to 1 mole of castor oil. Dissolved. The solution was poured into 100,000 parts by weight of water and allowed to disperse well to obtain an aqueous dispersion containing 0.02% by weight of the active compound. IV. Active compound No., No. 13.9 20 parts by weight was mixed well with 3 parts by weight of sodium salt of diisobutylnaphthalene-α-sulfonic acid, 17 parts by weight of sodium salt of lignosulfonic acid and 60 parts by weight of powdered silica gel from the sulfite waste solution, and mixtures thereof Was milled with a hammer grinder. The mixture was well dispersed in 20,000 parts by weight of water to obtain a spray mixture containing 0.1% by weight of active compound. V. Active Compound No., 13.5 3 parts by weight were mixed with 97 parts by weight of well-divided kaolin. In this way a powder containing 3% by weight of active compound was obtained. VI. Active Compound No., 13.15 20 parts by weight 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 inorganic oil Mix well. A stable oil dispersion was obtained. VII. Active Compound No. No. 13.16 1 part by weight was dissolved in a mixture comprising 70 parts by weight of cyclohexanone, 20 parts by weight of ethoxylated isooctylphenyl and 10 parts by weight of ethoxylated castor oil. A stable emulsion concentrate was obtained. VIII. Active Compound No., 13.17 1 part by weight in a mixture comprising 80 parts by weight of cyclohexanone and 20 parts by weight of Wetol® EM 31 (= nonionic emulsifier based on ethoxylated castor oil) Dissolved. A stable emulsion concentrate was obtained. The active compound I or preparation composition can be added before or after germination. If the active compound is less resistant to certain crops, an application technique can be used in which the preparation composition is sprayed with the aid of a spraying device, in which way they contact as little as possible, even if in contact with the leaves of sensitive crops, whereas the active compound Reaches undesired leaf or exposed soil surfaces that grow below (post-directed, lay-by). Depending on the purpose of inhibition, the number of years, the subject plants and the stage of growth, the use of the active compound is between 0.01 and 3.0, preferably 0.01 to 1.0 kg of active substance (a.s.) per hectare. To broaden the spectrum of action and obtain a synergistic effect, benzoyl derivative I can be added in combination with a number of other representative herbicides or groups of growth regulating active compounds. Suitable components of the mixture include, for example, 1,2,4-thiadiazole, 1,3,4-thiadiazole, amides, aminophosphoric acid and derivatives thereof, aminotriazoles, anilides, aryloxy / heteroaryloxy alka Nosane and its derivatives, benzoic acid and its derivatives, benzothiadiazinone, 2- (heteroaryl / aroyl-1,3-cyclohexanedione, heteroaryl arylketone, benzylisoxazolidinone, meta-CF 3 -phenyl derivative , Carbamate, quinolinecarboxylic acid and derivatives thereof, chloroacetanilide, cyclohexane-1,3-dione derivatives, diazine, dichloropropionic acid and derivatives thereof, dihydrobenzofuran, dihydrofuran-3-one, di Nitroaniline, dinitrophenol, diphenyl ether, dipyridyl, halocarboxylic acid and derivatives thereof, urea, 3-phenyluracil, imidazole, imidazolinone, N-phenyl-3,4,5,6- Tetrahydrophthalimide, oxadiazole, oxirane, phenol, aryl jade And heteroaryloxyphenoxypropionic acid esters, phenylacetic acid and derivatives thereof, 2-phenylpropionic acid and derivatives thereof, pyrazole, phenylpyrazole, pyrazine, pyridinecarboxylic acid and derivatives thereof, pyrimidyl ether, sulfonamide, sulfonyl Urea, triazine, triazinone, triazolinone, triazolecarboxamide and uracil. In addition, it may be useful to add Compound I in combination with other herbicides or alone, for example by further mixing plant protection agents such as insecticides or agents that inhibit plant pathological fungi or bacteria. Also important is compatibility with inorganic salt solutions used to eliminate nutrients and trace element deficiencies. Non-phytotoxic oils and oil concentrates may also be added. <Use example> The herbicidal action of the benzoyl derivatives of formula I can be shown in the following greenhouse experiments: The culture vessel used was a plastic flower pot and contained loamy soils with about 3.0% humus added as substrate. Seeds of the test plants were sprinkled separately for each kind. In the case of pre-germination treatment, the seeding was applied directly after sowing using a nozzle to distribute the active ingredients suspended or emulsified in water well. Water was added to the container to promote germination and growth and covered with a clear plastic hood until the plant took root. If the test plant is not adversely affected by the active ingredient, this cover allows the test plant to germinate constantly. For post-germination treatment the test plants were first grown to a plant height of 3 to 15 cm depending on the plant properties and then treated with the active ingredients suspended or emulsified in water. Finally, the test plants were sown directly and grown in the same container, or they were first grown separately as seedlings, and then transferred into the test container a few days before treatment. The utilization rate for post-germination treatment is 0.5 to 0.25 kg a hectare. It was s. The plants were kept at 10-25 ° C or 20-35 ° C depending on the type. The trial period was extended from 2 to 4 weeks. During this time, plants were grown and their response to each treatment was evaluated. The range of 0-100 was used for evaluation. 100 means no germination or at least complete destruction of the gaseous part of the plant, 0 means intact or normal growth. The plants used in the greenhouse experiment consisted of the following types: Compound of formula BotanyCommon name Chenopodium album (CHEAL)Lambs-quarters (museum) Ipomoea subspecies (IPOSS)Morning glory Sinapis alba (SINAL)White mustard Solanum nigrum (SOLNI)Crow Paper (black nightshade) Triticum aestivum (TRZAS)Summer wheet Zea mays (ZEAMX)Indian corn Herbicidal activity when used after germination in a greenhouse Example number13.3 Utilization rate (kgs / ha of a.s.)0.50.25 Test plantdamaged% TAZAS00 CHEAL9595 SINAL9595 SOLNI10095 Herbicidal activity when used after germination in a greenhouse Example number13.13 Utilization rate (kgs / ha of a.s.)0.50.25 Test plantdamaged% ZEAMX100 CHEAL9595 IPOSS100100 SOLNI100100
权利要求:
Claims (13) [1" claim-type="Currently amended] Benzoyl derivatives of formula I and agriculturally available salts. <Formula I> Where L and M are hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 4 -alkoxy, wherein these groups are from 1 to 5 halogens Or unsubstituted or substituted with an atom or C 1 -C 4 -alkoxy), halogen, cyano, nitro,-(A) m -S (O) n R 1 group or-(A) m -CO-R 2 groups; Y is C = O, C = NR 3 , CR 7 -NR 5 R 6 , CR 7 -OR 8 , CR 10 R 11 , CR 7 -SR 8 ; 1,3-dioxanyl or 1,3-dioxolanyl substituted with hydrogen or C 1 -C 4 -alkyl; A group selected from a hetero atom selected from oxygen, sulfur and nitrogen; X is (-CR 12 R 13- ), (-CR 12 R 13 -CR 21 R 22- ), (-CR 12 = CR 13- ), (-CR 12 R 13 -CR 12 = CR 13- ) ; Consisting of NR 23 , wherein the bond between X and Y may be saturated or unsaturated; A is O or NR 14 ; m is 0 or 1; n is 0, 1 or 2; R 1 is C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl or NR 14 ; R 2 is C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or NR 14 ; R 3 is hydrogen, —NR 9 R 4 ; C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -halo Alkenyl, C 2 -C 6 -alkynyl; Unsubstituted or substituted phenyl wherein the substituents are C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkyl, halogen, cyano, Nitro is selected as defined for Compound I); Unsubstituted or substituted benzyl, wherein the substituents are C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkyl, halogen, cyano, Nitro); Unsubstituted or substituted benzyloxy wherein the substituents are C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkyl, halogen, cyano Is selected from nitro); R 4 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C═O—NR 14 ; Unsubstituted or substituted phenyl wherein the substituents are C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkyl, halogen, cyano, Nitro); Unsubstituted or substituted benzyl, wherein the substituents are C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkyl, halogen, cyano, Selected from nitro); R 9 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C═O—NR 14 ; Unsubstituted or substituted phenyl wherein the substituents are C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkyl, halogen, cyano, Nitro); Unsubstituted or substituted benzyl, wherein the substituents are C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkyl, halogen, cyano, Selected from nitro); R 5 and R 6 independently of one another are hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 1 -C 4 -haloalkyl, C 2 -C 6 -haloalkenyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy; Unsubstituted or substituted phenyl wherein the substituents are C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkyl, halogen, cyano, Nitro); Unsubstituted or substituted benzyl, wherein the substituents are C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkyl, halogen, cyano, Selected from nitro); R 7 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy; Substituted or unsubstituted phenyl, wherein the substituent is selected from 1 to 3 halogens, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, nitro; R 7 and R 21 or R 7 and R 23 or R 7 and R 12 may form a bond; R 8 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 4 -haloalkyl, unsubstituted or substituted phenyl, wherein the substituents are C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkyl, halogen, cyano, nitro); Unsubstituted or substituted benzyl, wherein the substituents are C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkyl, halogen, cyano, Selected from nitro); R 10 and R 11 are, independently from each other, hydrogen, C 1 -C 6 -alkyl; Unsubstituted or substituted phenyl, wherein the substituent is selected from 1 to 3 halogens, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, nitro; R 10 and R 12 or R 10 and R 23 or R 10 and R 21 may form a bond; R 12 and R 13 are, independently from each other, hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy; Unsubstituted or substituted phenyl, wherein the substituents are C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkyl, halogen, cyano, Selected from nitro); R 14 is C 1 -C 4 -alkyl; R 21 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy; Unsubstituted or substituted phenyl, wherein the substituents are C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkyl, halogen, cyano, Selected from nitro); R 22 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy; Unsubstituted or substituted phenyl, wherein the substituents are C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkyl, halogen, cyano, Selected from nitro); R 23 is hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 1 -C 6 -alkoxy, phenyl or benzyl (which is C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy , Unsubstituted or substituted with C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkyl, halogen, cyano, nitro); Q is a cyclohexane-1,3-dione ring of Formula II, which is bonded at the 2-position; <Formula II> (In the meal, R 15 , R 16 , R 18 and R 20 are hydrogen or C 1 -C 4 -alkyl; R 19 is hydrogen, C 1 -C 4 -alkyl or —COOR 14 group; R 17 is hydrogen, C 1 -C 4 -alkyl, C 3 -C 4 -cycloalkyl, wherein these groups are preferably 1 in halogen, C 1 -C 4 -alkylthio or C 1 -C 4 -alkoxy To three substituents), or R 17 is tetrahydropyran-3-yl, tetrahydropyran-4-yl or tetrahydrothiopyran-3-yl, or R 17 and R 20 together form a bond or form a 3 to 6 membered carbocyclic ring) If, however, the Y = C = O, X is not NR 23. [2" claim-type="Currently amended] Benzoyl Derivatives of Formula Ia. <Formula Ia> Where L is hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1- C 4 -haloalkyl, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkylthio, C 1 -C 4 -alkylsulfonyl, halogen, nitro or cyano, M is hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1- C 4 -haloalkyl, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkylthio, C 1 -C 4 -alkylsulfonyl, halogen, nitro or cyano, Q, X, n and Y have the meanings defined in claim 1, When Y = C = O, X is not NR 23 . [3" claim-type="Currently amended] Benzoyl Derivatives of Formula (lb). <Formula Ib> Where L is C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl, C 1 -C 4 Haloalkoxy, halogen, nitro or cyano, M is hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl, C 1- C 4 -haloalkoxy, halogen, nitro or cyano, Q, X, n and Y have the meanings defined in claim 1, When Y = C = O, X is not NR 23 . [4" claim-type="Currently amended] The benzoyl derivative of formula I according to claim 1, wherein L and M are hydrogen, methyl, methoxy, chlorine, cyano, nitrile or trifluoromethyl. [5" claim-type="Currently amended] Benzoyl Derivatives of Formula (Ic). <Formula Ic> Where L is hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl, C 1- C 4 -haloalkoxy, halogen, nitro or cyano, M is hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl, C 1- C 4 -haloalkoxy, halogen, nitro or cyano, Q, n, Y and R 22 , R 21 , R 12 and R 13 have the meanings defined in claim 1. [6" claim-type="Currently amended] Benzoyl Derivatives of Formula Id. <Formula Id> Where L is hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl, C 1- C 4 -haloalkoxy, halogen, nitro or cyano, M is hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl, C 1- C 4 -haloalkoxy, halogen, nitro or cyano, Q, n, Y, R 12 and R 13 have the meanings defined in claim 1. [7" claim-type="Currently amended] Benzoyl Derivatives of Formula (Ie). <Formula Ie> Where L is hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl, C 1- C 4 -haloalkoxy, halogen, nitro or cyano, M is hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl, C 1- C 4 -haloalkoxy, halogen, nitro or cyano, Q, n, Y, R 12 and R 13 have the meanings defined in claim 1. [8" claim-type="Currently amended] 2. The benzoyl derivative of claim 1, wherein n is 1 or 2 and Y is CR 7 -OR 8 , wherein R 7 and R 8 have the meanings defined in claim 1. [9" claim-type="Currently amended] A compound of formula I as claimed in claim 1 consisting of acylating the starting material of formula II with an acid chloride of formula IIIa or an acid of compound IIIb and rearranging the acylation product in the presence of a catalyst Method of preparation. <Formula II> <Formula IIIa> <Formula IIIb> Wherein L, M, X, n and Y have the meaning defined in claim 1. [10" claim-type="Currently amended] A herbicide composition comprising at least one benzoyl derivative of formula (I) as claimed in claim 1 and a conventional inert additive. [11" claim-type="Currently amended] A method of inhibiting an undesirable plant, consisting of causing the herbicidally active amount of the benzoyl derivative of formula (I) as claimed in claim 1 to act on the plant or its habitat. [12" claim-type="Currently amended] Benzoyl Derivatives of Formula IIIc. <Formula IIIc> Where T is chlorine, OH or C 1 -C 4 -alkoxy; L is hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl, C 1- C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio, C 1 -C 4 -alkylsulfonyl, halogen, nitro or cyano; M is hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl, C 1- C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio, C 1 -C 4 -alkylsulfonyl, halogen, nitro or cyano; X, Y and n have the meanings defined in claim 1, provided that when X is (-CH 2 -CH 2- ) or (-CH 2- ) and Y is C = O or oxygen, then L and M are Except that at the same time it cannot be hydrogen and X cannot be NR 23 when Y = C = O. [13" claim-type="Currently amended] Benzoyl Derivatives of Formula IIId. <Formula IIId> Where T is chlorine, OH or C 1 -C 4 -alkoxy; L is C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl, C 1 -C 4 - haloalkoxy, C 1 -C 4 - alkylthio, C 1 -C 4 -halo-alkyl thio, C 1 -C 4 - alkylsulfonyl, halogen, nitro or cyano, and; M is hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl, C 1- C 4 - haloalkoxy, C 1 -C 4 - alkylthio, C 1 -C 4 - haloalkyl thioalkyl, C 1 -C 4 - alkylsulfonyl, halogen, nitro or cyano; X, Y and n have the meanings defined in claim 1, provided that when Y = C = O, X is not NR 23 .
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同族专利:
公开号 | 公开日 AR003688A1|1998-09-09| CZ60198A3|1998-08-12| MX9801292A|1998-05-31| TW334430B|1998-06-21| CA2227934A1|1997-03-13| JP2000026458A|2000-01-25| PL325204A1|1998-07-06| DE19532311A1|1997-03-06| GEP20012443B|2001-02-10| AU6929796A|1997-03-27| HU9802430A2|1999-02-01| US6054414A|2000-04-25| NZ316942A|2000-01-28| ZA9607313B|1998-03-02| HU9802430A3|2002-01-28| CN1194641A|1998-09-30| SK24398A3|1999-01-11| EA001202B1|2000-12-25| AU717015B2|2000-03-16| WO1997009324A1|1997-03-13| JP3027196B2|2000-03-27| CN1100052C|2003-01-29| JPH10510846A|1998-10-20| BR9610208A|1999-02-02| EA199800233A1|1998-10-29| IL123165A|2001-08-08| KR100446200B1|2005-08-05| EP0847394A1|1998-06-17| BG102297A|1998-12-30| IL123165D0|1998-09-24|
引用文献:
公开号 | 申请日 | 公开日 | 申请人 | 专利标题
法律状态:
1995-09-01|Priority to DE1995132311 1995-09-01|Priority to DE19532311.4 1996-08-29|Application filed by 스타르크, 카르크, 바스프 악티엔게젤샤프트 1999-06-25|Publication of KR19990044329A 2005-08-05|Application granted 2005-08-05|Publication of KR100446200B1
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申请号 | 申请日 | 专利标题 DE1995132311|DE19532311A1|1995-09-01|1995-09-01|Benzoyl derivatives| DE19532311.4|1995-09-01| 相关专利
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