Utilizing spirocyclic phenyl keto-enols as pesticides and herbicides

A compound of the formula (I) according to claim 1

• in which
• X represents fluorine, chlorine, bromine, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-halogenoalkyl, C1-C4-halogenoalkoxy, nitro or cyano,
• Y represents hydrogen, fluorine, chlorine, bromine, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-halogenoalkyl, C1-C4-halogenoalkoxy, nitro or cyano,
• Z represents fluorine, chlorine, bromine, C1-C4-alkyl, C1-C4-halogenoalkyl, C1-C4-alkoxy, C1-C4-halogenoalkoxy, nitro or cyano,
• n represents 0, 1 or 2,
• Het represents one of the groups
• G represents hydrogen (a) or represents one of the groups
• in which
• E represents a metal ion equivalent or an ammonium ion,
• L represents oxygen or sulphur and
• M represents oxygen or sulphur,
• R1 represents C1-C16-alkyl, C2-C16-alkenyl, C1-C6-alkoxy-C1-C6-alkyl or C1-C6-alkylthio-C1-C6-alkyl, each of which is optionally substituted by fluorine or chlorine, or represents C3-C7-cycloalkyl which is optionally substituted by fluorine, chlorine, C1-C5-alkyl or C1-C5-alkoxy,
• represents phenyl which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C1-C4-alkyl, C1-C4-alkoxy, C1-C3-halogenoalkyl or C1-C3-halogenoalkoxy,
• represents phenyl-C1-C4-alkyl which is optionally substituted by fluorine, chlorine, bromine, C1-C4-alkyl, C1-C4-alkoxy, C1-C3-halogenoalkyl or C1-C3-halogenoalkoxy or
• represents pyrazolyl, thiazolyl, pyridyl, pyrimidyl, furanyl or thienyl, each of which is optionally substituted by fluorine, chlorine, bromine or C1-C4-alkyl,
• R2 represents C1-16-alkyl, C2-C16-alkenyl, C1-C6-alkoxy-C2-C6-alkyl or poly-C1-C6-alkoxy-C2-C6-alkyl, each of which is optionally substituted by fluorine,
• represents C3-C7-cycloalkyl which is optionally substituted by fluorine, chlorine, C1-C4-alkyl or C1-C4-alkoxy or represents phenyl or benzyl, each of which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C1-C4-alkyl, C1-C3-alkoxy, C1-C3-halogenoalkyl or C1-C3-halogenoalkoxy,
• R3 represents C1-C6-alkyl which is optionally substituted by fluorine or chlorine or represents phenyl or benzyl, each of which is optionally substituted by fluorine, chlorine, bromine, C1-C5-alkyl, C1-C5-alkoxy, C1-C3-halogenoalkyl, C1-C3-halogenoalkoxy, cyano and nitro,
• R4 and R5 independently of one another each represent C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylamino, di-(C1-C6-alkyl)amino, C1-C6-alkylthio, C3-C4-alkenylthio or C3-C6-cycloalkylthio, each of which is optionally substituted by fluorine or chlorine, or represents phenyl, phenoxy, phenylthio, each of which is optionally substituted by fluorine, chlorine, bromine, nitro, cyano, C1-C3-alkoxy, C1-C3-halogenoalkoxy, C1-C3-alkylthio, C1-C3-halogenoalkylthio, C1-C3-alkyl or C1-C3-halogenoalkyl,
• R6 and R7 independently of one another each represent hydrogen, represent C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C3-C6-alkenyl or C1-C6-alkoxy-C1-C6-alkyl, each of which is optionally substituted by fluorine or chlorine, represent phenyl which is optionally substituted by halogen, C1-C5-halogenoalkyl, C1-C5-alkyl or C1-C5-alkoxy, represent benzyl which is optionally substituted by halogen, C1-C5-alkyl, C1-C5-halogenoalkyl or C1-C5-alkoxy or together represent a C3-C6-alkylene radical in which optionally one methylene group which is not directly adjacent to the nitrogen atom is replaced by oxygen or sulphur,
• Q represents
• R9 represents hydrogen, represents C1-C6-alkyl, which is optionally substituted by fluorine or chlorine, represents C3-C7-cycloalkyl or represents phenyl or benzyl, each of which is optionally substituted by fluorine, chlorine, bromine, C1-C5-alkyl, C1-C4-alkoxy, C1-C2-halogenoalkyl, C1-C2-halogenoalkoxy, nitro or cyano, represents pyrimidiyl or thiazolyl or represents CO—R1′, CO2R2′, SO2R1′, CONH2, CONHR11 or
• R10 represents hydrogen or C1-C6-alkyl,
• R11 and R12 are identical or different and each represents C1-C4-alkyl,
• m represents 1,
• R1′ independently of R1 represents the substituents defined previously within this claim 3 for R1 and
• R2′ independently of R2 represents the substituents defined previously within this claim 3 for R2.

A compound of the formula (I) according to claim 1,

• in which
• X represents fluorine, chlorine, bromine, methyl, ethyl, n-propyl, iso-propyl, methoxy, ethoxy, n-propoxy, iso-propoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy, nitro or cyano,
• Y represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, iso-propoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy, nitro or cyano,
• Z represents fluorine, chlorine, bromine, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, iso-propoxy, difluoromethoxy, trifluoromethoxy, nitro or cyano,
• n represents 0, 1 or 2,
• Het represents one of the groups
• G represents hydrogen (a) or represents one of the groups
• in which
• E represents a metal ion equivalent or an ammonium ion,
• L represents oxygen or sulphur and
• M represents oxygen or sulphur,
• R1 represents C1-C14-alkyl, C2-C14-alkenyl, C1-C4-alkoxy-C1-C6-alkyl or C1-C4-alkylthio-C1-C6-alkyl, each of which is optionally substituted by fluorine or chlorine, or represents C3-C6-cycloalkyl, which is optionally substituted by methyl, ethyl, tert-butyl or methoxy,
• represents phenyl which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, methyl, methoxy, trifluoromethyl or trifluoromethoxy,
• represents benzyl which is optionally substituted by fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl or trifluoromethoxy or
• represents furanyl, thienyl or pyridyl, each of which is optionally substituted by fluorine, chlorine, bromine or methyl,
• R2 represents C1-C14-alkyl, C2-C14-alkenyl or C1-C4-alkoxy-C2-C6-alkyl,
• represents C3-C6-cycloalkyl which is optionally substituted by methyl or methoxy or
• represents phenyl or benzyl, each of which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, methyl, methoxy, trifluoro-methyl or trifluoromethoxy,
• R3 represents methyl, ethyl, n-propyl, isopropyl, each of which is optionally substituted by fluorine or chlorine, or represents phenyl or benzyl, each of which is optionally substituted by fluorine, chlorine, bromine, methyl, ethyl, n-propyl, iso-propyl, tert-butyl, methoxy, ethoxy, isopropoxy, tert-butoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro,
• R4 and R5 independently of one another each represent C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkylamino, di-(C1-C4-alkyl)amino or C1-C4-alkylthio, each of which is optionally substituted by fluorine or chlorine, or represent phenyl, phenoxy or phenylthio, each of which is optionally substituted by fluorine, chlorine, bromine, nitro, cyano, C1-C2-alkoxy, C1-C2-fluoroalkoxy, C1-C2-alkylthio, C1-C2-fluoroalkylthio or C1-C3-alkyl,
• R6 and R7 independently of one another each represent hydrogen, represent C1-C4-alkyl, C3-C6-cycloalkyl, C1-C4-alkoxy, C3-C4-alkenyl or C1-C4-alkoxy-C1-C4-alkyl, each of which is optionally substituted by fluorine or chlorine, represent phenyl which is optionally substituted by fluorine, chlorine, bromine, trifluoromethyl, methyl or methoxy, represent benzyl which is optionally substituted by fluorine, chlorine, bromine, C1-C4-alkyl, C1-C4-halogenoalkyl or C1-C4-alkoxy or together represent a C5-C6-alkylene radical in which optionally one methylene group which is not directly adjacent to nitrogen atom may be replaced by oxygen or sulphur,
• Q represents
• R9 represents hydrogen, represents C1-C4-alkyl, represents C3-C6-cycloalkyl or represents phenyl or benzyl, each of which is optionally substituted by fluorine, chlorine, bromine, methyl, ethyl, n-propyl, iso-propyl, tert-butyl, methoxy, trifluoromethyl, trifluoromethoxy, nitro or cyano, or represents CO—R1′, CO2R2′, SO2R1′, CONH2, CONHR11 or
• R10 represents hydrogen or methyl,
• R11 and R12 are identical or different and each represents methyl or ethyl,
• m represents 1,
• R1′ independently of R1 represents the substituents defined previously within this claim 4 for R1 and
• R2′ independently of R2 represents the substituents defined previously within in this claim 4 for R2.

A process for preparing compounds of the formula (I) according to claim 1, characterised in that to obtain compounds

• (A) of the formula (I-1-a)
• in which
• Q, X, Y, Z, m and n are each as defined in claim 2,
• compounds of the formula (II)
• in which
• Q, X, Y, Z, m and n are each as defined in claim 2,
• and
• R8 represents alkyl
• are intramolecularly condensed in the presence of a diluent and in the presence of a base,
• (B) to obtain compounds of the formula (I-2-a)
• in which
• Q, X, Y, Z, m and n are each as defined in claim 2,
• compounds of the formula (III)
• in which
• Q, X, Y, Z, m, and n are each as defined in claim 2 and R8 is as previously defined in this claim 5,
• are intramolecularly condensed in the presence of a diluent and in the presence of a base,
• (C) to obtain compounds of the formula (I-3-a)
• in which
• Q, X, Y, Z, m and n are each as defined in claim 2,
• compounds of the formula (IV)
• in which
• Q, X, Y, Z, m and n are as defined in claim 2 and R8 is as defined in this claim 5, and
• W represents hydrogen, halogen, alkyl, preferably C1-C6 alkyl, or alkoxy, preferably C1-C8-alkoxy
• are intramolecularly cyclized in the presence of a diluent and in the presence of an acid, and the resulting compounds of the formulae (I-1-a), (I-2-a) and (I-3-a) are each optionally subsequently
• (Dα) reacted with acyl chlorides of the formula (V)
• in which
• R1 is as defined in claim 2 and
• Hal represents halogen
• or
• (Dβ) reacted with carboxylic anhydrides of the formula (VI)
• R1—CO—O—CO—R1 (VI)
• in which
• R1 is as defined in claim 2,
• optionally in the presence of a diluent and optionally in the presence of an acid binder;
• or
• (E) reacted with chloroformic acid esters or chloroformic acid thiol esters of the formula (VII)
• R2—M—CO—Cl (VII)
• in which
• R2 and M are each as defined in claim 2,
• optionally in the presence of a diluent and optionally in the presence of an acid binder;
• or
• (F) reacted with chloromonothioformic acid esters or chlorodithioformic acid esters of the formula (VIII)
• in which
• M and R2 are each as defined in claim 2,
• optionally in the presence of a diluent and optionally in the presence of an acid binder;
• or
• (G) reacted with sulphonyl chlorides of the formula (IX)
• R3—SO2—Cl (IX)
• in which
• R3 is as defined in claim 2,
• optionally in the presence of a diluent and optionally in the presence of an acid binder;
• or
• (H) reacted with phosphorus compounds of the formula (X)
• in which
• L, R4 and R5 are each as defined in claim 2 and
• Hal represents halogen,
• optionally in the presence of a diluent and optionally in the presence of an acid binder;
• or
• (I) reacted with metal compounds or amines of the formula (XI) or (XII)
• Me(OR13)t (XI)
• in which
• Me represents a mono- or divalent metal,
• t represents 1 or 2 and
• R13, R14, R15 independently of one another each represent hydrogen or alkyl,
• optionally in the presence of a diluent;
• or
• (Jα) reacted with isocyanates or isothiocyanates of the formula (XIII)
• R6—N═C═L (XIII)
• in which
• R6 and L are each as defined in claim 2,
• optionally in the presence of a diluent and optionally in the presence of a catalyst or
• (Jβ) reacted with carbamoyl chlorides or thiocarbamoyl chlorides of the formula (XIV)
• in which
• L, R6 and R7 are each as defined in claim 2,
• optionally in the presence of a diluent and optionally in the presence of an acid binder.

A compound of the formula (I)

• in which
• X represents halogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkinyl, C1-C6-alkoxy, C3-C6-alkenyloxy, C1-C6-alkylthio, C1-C6-alkylsulphinyl, C1-C6-alkylsulphonyl, C1-C6-halogenoalkyl, C2-C6-halogenoalkenyl, C1-C6-halogenoalkoxy, C3-C6-halogenoalkenyloxy, nitro, cyano or represents phenyl, phenoxy, phenylthio, benzyloxy or benzylthio, each of which is optionally substituted by halogen, C1-C6-alkyl, C1-C6-alkoxy, C1-C4-halogenoalkyl, C1-C4-halogenoalkoxy, nitro or cyano,
• Y represents hydrogen, halogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkinyl, C1-C6-alkoxy, C3-C6-alkenyloxy, C1-C6-alkylthio, C1-C6-alkyls C1-C6-alkylsulphonyl, C1-C6-halogenoalkyl, C2-C6-halogenoalkenyl, C1-C6-halogenoalkoxy, C3-C6-halogenoalkenyloxy, nitro or cyano,
• Z represents halogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkinyl, C1-C6-halogenoalkyl, C2-C6-halogenoalkenyl, C1-C6-alkoxy, C3-C6-alkenyloxy, C1-C6-halogenoalkoxy, C3-C6-halogenoalkenyloxy, nuitro or cyano,
• n represents 0, 1, 2 or 3,
• Het represents one of the groups
• G represents hydrogen (a) or represents one of the groups
• in which
• E represents a metal ion equivalent or an ammonium ion,
• L represents oxygen or sulphur and
• M represents oxygen or sulphur,
• R1 represents C1-C20-alkyl, C2-C20-alkenyl, C1-C8-alkoxy-C1-C8-alkyl, C1-C8-alkylthio-C1-C8-alkyl or poly-C1-C8-alkoxy-C1-C8-alkyl, each of which may optionally be substituted with halogen,
• represents C3-C8-cycloalkyl which may optionally be substituted by halogen, C1-C6-alkyl or C1-C6-alkoxy and in which optionally one or at most two not directly adjacent methylene groups may be replaced by oxygen and/or sulphur,
• represents phenyl which is optionally substituted by halogen, cyano, nitro, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-halogenoalkyl, C1-C6-halogenoalkoxy, C1-C6-alkylthio or C1-C6-alkylsulphonyl,
• represents phenyl-C1-C6-alkyl, which is optionally substituted by halogen, nitro, cyano, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-halogenoalkyl or C1-C6-halogenoalkoxy,
• represents 5- or 6-membered hetaryl selected from pyrazolyl, thiazolyl, pyridyl, pyrimidyl, furanyl and thienyl each of which is optionally substituted by halogen or C1-C6-alkyl,
• represents phenoxy-C1-C6-alkyl which is optionally substituted by halogen or C1-C6-alkyl or
• represents 5- or 6-membered hetaryloxy-C1-C6-alkyl which is optionally substituted by halogen, amino or C1-C6-alkyl,
• R2 represents C1-C20-alkyl, C2-C20-alkenyl, C1-C8-alkoxy-C2-C8-alkyl or poly-C1-C8-alkoxy-C2-C8-alkyl, each of which is optionally substituted by halogen,
• represents C3-C8-cycloalkyl which is optionally substituted by halogen, C1-C6-alkyl or C1-C6-alkoxy or
• represents phenyl or benzyl, each of which is optionally substituted by halogen, cyano, nitro, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-halogenoalkyl or C1-C6-halogenoalkoxy,
• R3 represents C1-C8-alkyl which is optionally substituted by halogen or represents phenyl or benzyl, each of which is optionally substituted by halogen, C1-C6-alkyl, C1-C6-alkoxy, C1-C4-halogenoalkyl, C1-C4-halogenoalkoxy, cyano or nitro,
• R4 and R5 independently of one another each represent C1-C8-alkyl, C1-C8-alkoxy, C1-C8-alkylamino, di-(C1-C8-alkyl)amino, C1-C8-alkylthio, C2-C8-alkenylthio, C3-C7-cycloalkylthio, each of which is optionally substituted by halogen, or represent phenyl, phenoxy or phenylthio, each of which is optionally substituted by halogen, nitro, cyano, C1-C4-alkoxy, C1-C4-halogenoalkoxy, C1-C4-alkylthio, C1-C4-halogenoalkylthio, C1-C4-alkyl or C1-C4-halogenoalkyl,
• R6 and R7 independently of one another each represent hydrogen, represent C1-C8-alkyl, C3-C8-cycloalkyl, C1-C8-alkoxy, C3-C8-alkenyl or C1-C8-alkoxy-C1-C8-alkyl, each of which is optionally substituted by halogen, represent phenyl which is optionally substituted by halogen, C1-C8-halogenoalkyl, C1-C8-alkyl or C1-C8-alkoxy, represent benzyl which is optionally substituted by halogen, C1-C8-alkyl, C1-C8-halogenoalkyl or C1-C8-alkoxy or together represent a C3-C6-alkylene radical in which optionally one methylene group which is not directly adjacent to the nitrogen atom is replaced by oxygen or sulphur,
• Q represents
• R9 represents hydrogen, represents C1-C8-alkyl which is optionally substituted by halogen, represents C3-C8-cycloalkyl which is optionally substituted by halogen, C1-C4-alkyl or C1-C4-alkoxy or represents phenyl, benzyl or hetaryl selected from pyridyl, pyrimidyl and thiazolyl, each of which is optionally substituted by halogen, C1-C6-alkyl, C1-C4-alkoxy, C1-C4-halogenoalkyl, C1-C4-halogenoalkoxy, nitro or cyano, or represents CO—R1′, CO2R2′, SO2R1′, CONH2, CONHR11 or
• R10 represents hydrogen or C1-C8-alkyl,
• R11 and R12 are identical or different and each represent C1-C6-alkyl or C3-C6-alkenyl,
• m represents 0 or 1,
• R1′ independently of R1 represents the substituents defined previously within this claim for R1
• and
• R2′ independently of R2 represents the substituents defined previously within this claim for R2.