Patent EP-2740356-A1 (EP)
Inventor: MÜLLER THOMAS DR
IPC: A01P21/00
Filed: 2012-12-05
Abstract: Use of substituted (2Z)-5-(1-hydroxycyclohexyl)pent-2-en-4-ynoic acid derivatives (I) for increasing tolerance of plants against abiotic stress, is claimed. Use of substituted (2Z)-5-(1-hydroxycyclohexyl)pent-2-en-4-ynoic acid derivatives of formula (I) or their salts for increasing tolerance of plants against abiotic stress, is claimed. X-Y1 : -CC-, (E)-ethene-1,2-diyl, (Z)-ethene-1,2-diyl or ethane-1,2-diyl; Q : ester moieties of formula (IIa) or (IIc), amide moieties of formula (IIb) or (IId) or 5H-furan-2-one-4-yl; either R1 : phenyl, heteroaryl, preferably aromatic heterocyclyl with 5-7 ring atoms, heterocyclyl with 5-7 ring atoms (saturated or partially unsaturated and containing 1-4 O, N or S) (all optionally substituted by halo, OH, 1-4C alkoxy or 1-4C alkylthio), 1-20C alkyl, 2-20C alkenyl, 2-20C alkynyl, 1-20C alkoxy or 1-20C alkylthio (all optionally halogenated), 3-20C cycloalkyl, 3-20C cycloalkyloxy, 3-20C cycloalkylthio, 3-20C cycloalkenyl, 3-20C cycloalkenyl-oxy, 3-20C cycloalkenyl-thio or NR11R12; and R2-R4 : H or R1; or 2 R1 which are bonded to same C, R1+R1+C to which 2 R1 are bonded, 2 R2 which are bonded to same C, R2+R2+C to which 2 R2 are bonded, 2 R3 which are bonded to same C, R3+R3+C to which 2 R3 are bonded, 2 R4 which are bonded to same C, R4+R4+C to which 2 R4 are bonded : 3-6C cycloalkyl; R11, R12 : hydrocarbyl (optionally substituted by 1-30C, preferably 1-20C moiety (optionally substituted by halo, OH, 1-4C alkoxy or 1-4C alkylthio)) or H; R5 : 1-20C alkyl, 2-20C alkenyl or 2-20C alkynyl (all optionally halogenated) or 3-20C cycloalkyl or 3-20C cycloalkenyl (both optionally substituted by halo, CN, OH, 1-4C alkoxy or 1-4C alkylthio), H or SiR21R22R23; R21-R23 : hydrocarbyl (optionally substituted by 1-30C moiety, preferably 1-20C moiety) or H; R6 : 3-20C cycloalkyloxy, 3-20C cycloalkylthio or 3-20C cycloalkenyl (all optionally substituted by halo, OH, 1-4C alkoxy or 1-4C alkylthio), or 2-20C alkyl, 2-20C alkenyl or 2-20C alkynyl (all optionally halogenated), H or 3-20C cycloalkyl; either R8 : H, 1-20C alkyl, 1-20C cycloalkyl, halo, 2-20C alkenyl, 2-20C alkynyl, 1-20C haloalkyl, 1-20C cyanoalkyl, 3-20C cycloalkyl-alkyl, (hetero)aryl-1-20C alkyl, 1-20C alkylcarbonyl, 1-20C alkoxycarbonyl, 1-20C alkenyloxy-carbonyl, 2-20C alkenyl-alkyloxycarbonyl, aryl-1-20C alkyloxycarbonyl, 3-20C cycloalkoxycarbonyl, 3-20C cycloalkyloxy-carbonyl, 1-20C alkylsulfonyl, arylsulfonyl, 3-20C cycloalkylsulfonyl, 1-20C alkylsulfinyl, arylsulfinyl, 3-20C cycloalkylsulfinyl, 1-20C alkoxycarbonyl-1-20C alkyl, hydroxycarbonyl-1-20C alkyl, arylalkoxycarbonyl-1-20C alkyl, 3-20C cycloalkyl-alkoxycarbonyl-1-20C alkyl, alkoxycarbonyl-3-20C cycloalkyl, hydroxycarbonyl-3-20C cycloalkyl, 1-20C alkoxycarbonyl-3-20C cycloalkenyl, hydroxycarbonyl-3-20C cycloalkenyl or bis-1-20C alkylamino-1-20C alkyl; and R9 : H, 1-20C alkyl, 3-20C cycloalkyl, halo, 1-20C haloalkyl, 2-20C alkynyl, 2-20C alkenyl, 1-20C cyanoalkyl, (hetero)aryl-1-20C alkyl, 1-20C alkylcarbonyl, 1-20C alkoxycarbonyl, 1-20C alkylsulfonyl, arylsulfonyl, 3-20C cycloalkylsulfonyl, 1-20C alkylsulfinyl, arylsulfinyl, 3-20C cycloalkylsulfinyl or 1-20C alkoxycarbonyl-1-20C alkyl; and R7 : 3-20C cycloalkyl, 3-20C cycloalkenyl or 3-20C cycloalkenyl-oxy (all optionally substituted by halo, OH, 1-4C alkoxy or 1-4C alkylthio), or 1-20C alkyl, 2-20C alkenyl or 2-20C alkynyl (all optionally halogenated), H or SiR21R22R23. An independent claim is also included for substituted (2Z)-5-(1-hydroxycyclohexyl)pent-2-en-4-ynoic acid derivatives of formula (Ib). Either R31 : phenyl, heteroaryl, preferably aromatic heterocyclyl with 5-7 ring atoms, heterocyclyl with 5-7 ring atoms (saturated or partially unsaturated and containing 1-4 O, N or S) (all optionally substituted by halo, OH, 1-4C alkoxy or 1-4C alkylthio), 1-6C alkyl, 2-6C alkenyl, 2-6C alkynyl, 1-6C alkoxy or 1-6C alkylthio (all optionally halogenated), 3-6C cycloalkyl, 3-6C cycloalkyloxy, 3-6C cycloalkylthio, 3-6C cycloalkenyl, 3-6C cycloalkenyl-oxy, 3-6C cycloalkenyl-thio or NR41R42; and R32-R34 : H or R31; or 2 R31 which are bonded to same C, R31+R31+C to which 2 R31 are bonded, 2 R32 which are bonded to same C, R32+R32+C to which 2 R32 are bonded, 2 R33 which are bonded to same C, R33+R33+C to which 2 R33 are bonded, 2 R34 which are bonded to same C, R34+R34+C to which 2 R34 are bonded : 3-6C cycloalkyl; R41, R42 : hydrocarbyl (optionally substituted by 1-30C) or H; R35 : 1-6C alkyl, 2-6C alkenyl or 2-6C alkynyl (all optionally halogenated) or 3-6C cycloalkyl or 3-6C cycloalkenyl (both optionally substituted by halo, CN, OH, 1-4C alkoxy or 1-4C alkylthio), H or SiR21R22R23; R36 : 3-8C cycloalkyloxy, 3-8C cycloalkylthio or 3-8C cycloalkenyl (all optionally substituted by halo, OH, 1-4C alkoxy or 1-4C alkylthio), or 2-8C alkyl, 2-8C alkenyl or 2-8C alkynyl (all optionally halogenated), H or 3-8C cycloalkyl; and R37 : 3-7C cycloalkyl, 3-7C cycloalkenyl or 3-7C cycloalkenyl-oxy (all optionally substituted by halo, OH, 1-7C alkoxy or 1-4C alkylthio), or 1-7C alkyl, 2-7C alkenyl or 2-7C alkynyl (all optionally halogenated), H or SiR21R22R23. [Image] [Image] [Image] ACTIVITY : Plant Protectant. The ability of (I) to increase cold stress tolerance in plants was tested in Zea mays. The results showed that (2Z)-5-(1-hydroxy-2,2,6-trimethylcyclohexyl)-3-methylpent-2-en-4-ynoic acid (25 g/ha) exhibited an efficacy (reduction in damage intensity), which is calculated as (damage value of untreated and stressed controls minus damage value of plants treated with test compound x 100) divided by damage value of untreated and stressed controls, of greater than 5%. MECHANISM OF ACTION : None given.