Patent EP-2719680-A1 (EP)
Inventor: ANGERMANN ALFRED DR
IPC: C07C69/157
Filed: 2011-10-28
Abstract: Phenyl substituted bicyclooctane-1,3-dione derivative (I) and its isomers comprising 3-hydroxy-2-phenyl-4,5,6,6a-tetrahydro-3aH-pentalen-1-one derivative (IIa) and (IIb), and 2-phenyl-tetrahydro-pentalene-1,3-dione derivative (IIc), are new. Phenyl substituted bicyclooctane-1,3-dione derivative of formula (I) and its isomers comprising 3-hydroxy-2-phenyl-4,5,6,6a-tetrahydro-3aH-pentalen-1-one derivative of formula (IIa) and (IIb), and 2-phenyl-tetrahydro-pentalene-1,3-dione derivative of formula (IIc), are new. either Y1 : -OR6, -S(O) pR6, -CO 2R7, -CH=CH 2, CN, -SCN, -CONR8R9, -SO 2NR8R9, -CR10=O, -NR11R12, -CR10=N-OR13, -CR10=N-R14, -CR10=N-NR15R16, -CR10(OR17OR18), -CR10(SR17OR18), -CR10(SR17SR18), -CR10(NHR17NHR18), -CR10(NHR17OR18), -CR10(NHR17SR18), -CH(CN) 2, -CH(OH)R6, halo, -O(C=M)R10, -S(C=M)R10, -O(C=M)NR11R12, -S(C=M)NR11R12, -NH(C=M)NR11R12, -O(C=M)OR7, -S(C=M)OR7, -NH(C=M)OR7 or W1 (when Q = bond, 1-3C alkylene, 2-3C alkenylene or 2-3C alkynylene); and R5 : H or 1-4C alkyl; or Q+Y1+R5 : CHCN=, CH(CO 2-1-6C alkyl)=, NC-C(CN)=, R7O-C(=O)-C(CN)= or R7O-C(=O)-C(C=O-OR7)=; W1 : 3-7 membered heterocyclyl (optionally partially saturated, contains O, S or N, and mono- or polysubstituted); G : CH 3, ethyl, benzyl (when Q+Y1+R5 = CH 2=), H, -C(=O)-R19, -C(=L)-M-R20, -SO 2-R21, -P(=L)(R22)-R23, E or -C(=L)-N(R24)-R25; E : metal ion equivalent, tertiary sulfonium ion or ammonium ion; L, M : O or S; R1 : 1-6C alkyl, 3-6C cycloalkyl, 2-6C alkenyl, 2-6C alkynyl, 1-6C alkoxy, 3-6C cycloalkoxy, 2-6C alkynyloxy, 2-6C alkenyloxy, 1-3C alkylthio, 1-3C alkylsulfinyl or 1-3C alkylsulfonyl (all optionally halogenated), H, halo, CN or NO 2; R2, R3 : phenyl (optionally mono- or polysubstituted by 1-4C alkyl, 3-6C cycloalkyl, 1-6C alkoxy (all optionally halogenated), halo, NO 2or CN), 1-6C alkyl, 2-6C alkenyl, 2-6C alkynyl, 1-6C alkoxy, 3-6C cycloalkoxy, 2-6C alkynyloxy, 2-6C alkenyloxy, 1-3C alkylthio, 1-3C alkylsulfinyl, 1-3C alkylsulfonyl (all optionally halogenated), 3-6C cycloalkyl, H, halo, CN or NO 2; R4 : 1-6C alkyl, 3-6C cycloalkyl, 1-6C alkoxy, 3-6C cycloalkoxy (all optionally halogenated), H, halo, CN or NO 2; R6 : benzyl, phenyl, heteroaryl, -CH 2-heteroaryl, -CH 2CH 2-heteroaryl, pyranyl, tetrahydrofuranyl, 1-4C alkanoyl (optionally halogenated) (all mono- or polysubstituted by 1-6C alkyl, 3-6C cycloalkyl, 2-6C alkynyl, 3-6C cycloalkoxy-1-6C alkyl (all optionally halogenated), halo-2-6C alkenyl, 1-4C alkoxyalkyl, halo-1-4C alkoxy-1-6C alkyl, halo, CN or NO 2), benzoyl (optionally mono- or polysubstituted by 1-6C alkyl, 3-6C cycloalkyl (both optionally halogenated), halo, CN or NO 2) or 1-6C alkyl, 3-6C cycloalkyl, 2-6C alkenyl, 2-6C alkynyl, 1-4C alkoxy-1-4C alkyl, 1-6C cycloalkoxy-1-4C alkyl (all optionally halogenated) or H; R7 : 1-6C alkyl, 3-6C cycloalkyl, 2-6C alkenyl (optionally substituted), H or E; either R8, R9 : phenyl, benzyl (both mono- or polysubstituted by halo, NO 2, CN or 1-3C alkyl), H, 1-6C alkyl, 2-6C alkenyl, 2-6C alkynyl or 3-6C cycloalkyl; or R8+R9+N : morpholino, piperidino or pyrrolidino; R10 : phenyl, benzyl (both optionally mono- or polysubstituted by 1-6C alkyl (optionally halogenated) or halo), 2-6C alkenyl (optionally halogenated), H, 1-6C alkyl, halo-1-4C alkyl, 2-6C alkynyl or 3-6C cycloalkyl; either R11, R12 : phenyl, benzyl (both mono- or polysubstituted by halo, NO 2, CN or 1-3C alkyl), H, 1-6C alkyl, 2-6C alkenyl, 2-6C alkynyl or 3-6C cycloalkyl; or R11+R12+N : morpholino, piperidino or pyrrolidino; R13 : 1-6C alkyl, 2-6C alkenyl, 2-6C alkynyl, 3-6C cycloalkyl, 3-6C cycloalkyl-1-3C alkyl (all optionally interrupted once or several times by O or S and all optionally mono- or polysubstituted by halo) or benzyl or -CH 2-heterocyclyl (both optionally mono- or polysubstituted by halo, NO 2, CN or 1-3C alkyl) or H; R14 : phenyl, benzyl (both mono- or polysubstituted by 1-3C alkyl, 3-6C cycloalkyl (both optionally halogenated), halo, NO 2or CN), H, 1-6C alkyl, 2-6C alkenyl or 2-6C alkynyl; either R15, R16 : phenyl, benzyl (both mono- or polysubstituted by halo, NO 2, CN or 1-3C alkyl), H, 1-5C alkyl, 2-6C alkenyl, 2-6C alkynyl or 3-6C cycloalkyl; or R15+R16+N : morpholino, piperidino or pyrrolidino; R17, R18 : 1-6C alkyl (optionally halogenated), benzyl (both optionally interrupted once or several times by O or S) or H; R19 : e.g. 1-6C alkyl and 2-6C alkenyl; R20 : e.g. 1-6C alkyl and 2-6C alkenyl; R21-R23 : e.g. 1-6C alkyl and 1-6C alkoxy; R24, R25 : 1-6C alkyl, 3-6C cycloalkyl, 2-6C alkenyl, 1-6C alkoxy, 1-6C alkoxy-1-4C alkyl (all optionally mono- or polysubstituted by halo), phenyl or benzyl (both optionally mono- or polysubstituted by halo or 1-4C alkyl) or H; R24+R25+N : morpholino, piperidino or pyrrolidino; and p : 0-2. Full definitions are given in the DEFINITIONS (Full Definitions) Field. Independent claims are also included for: (1) preparing (I); (2) a composition comprising (I) and at least one crop plant compatibility improving compound comprising 16 compounds e.g. phenyl derivative of formula (XVI); (3) controlling undesirable plant growth, comprising acting the above composition on the plants or their surroundings, or separately acting (I) and the above crop plant compatibility improving compounds, in close time successions, on the plants or their surroundings; (4) 2-phenylacetyl-cyclopentanecarboxylic acid derivative of formula (III); (5) 2-Phenylacetyl-cyclopentanecarboxylic acid derivative of formula (XV); and (6) 2-(2-carboxy-2-phenyl-acetyl)-cyclopentanecarboxylic acid derivative of formula (XVI). R26, R33 : alkyl; R36 : alkyl or H; n2 : 0-5, preferably 0-3; R41 : halo, 1-4C alkoxy, NO 2or 1-4C (halo)alkyl; W2 : divalent heterocyclyl (optionally substituted), preferably partially unsaturated or aromatic five-membered heterocyclyl with 1-3 N or O (where at least one N atom and not > 1 O atom is present in ring); R40 : 3-7 membered heterocyclyl with at least one N and upto 3 O or S, which is bonded to C=O in (XVI) through N (optionally saturated and optionally substituted by 1-4C alkyl, 1-4C alkoxy or optionally substituted phenyl), OR42, SR43 or NR42R43; R42 : 1-18C aliphatic hydrocarbyl (optionally substituted) or H; and R43 : phenyl (optionally substituted), H, 1-6C alkyl or 1-6C alkoxy. [Image] [Image] [Image] [Image] ACTIVITY : Pesticide; Herbicide. The herbicidal activity of (I) was tested against Alopecurus myosuroides. The results showed that 2-(2,6-diethyl-4-methylphenyl)-5-(1,3-dioxan-2-yl) tetrahydropentalen-1,3(2H,3aH)-dione exhibited the herbicidal activity of 100%. MECHANISM OF ACTION : None given.