Patent EP-2511255-A1 (EP)
Title: Substituted prop-2-in-1-ol and prop-2-en-1-ol derivatives
Inventor: MUELLER THOMAS
IPC: C07C409/04
Filed: 2011-04-15
Abstract: Substituted alcohol compounds (I) are new. Substituted alcohol compounds of formula (R4-C(R3)(R2)-C(R1)(O-R5)-(X-Y1)-Q) (I) or their salts are new. (X-Y1) : -CC-, (E)-ethene-1,2-diyl, (Z)-ethene-1,2-diyl or -CH 2-CH 2-; Q : -C(R6)=CH-C(=O)-O-R7, -C(R6)=CH-C(=O)-N(R8)-R9 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 (contains 1-4 O, N or S, partially saturated or unsaturated and all optionally substituted by G), 3-20C cycloalkyl, 1-20C (halo)alkyl, 1-20C (halo)alkenyl, 1-20C (halo)alkynyl, 1-20C (halo)alkoxy, 1-20C (halo)alkylthio, 3-20C cycloalkyloxy, 3-20C cycloalkylthio, 3-20C cycloalkenyl, 3-20C cycloalkenyl-oxy, 3-20C cycloalkenyl-thio, 1-20C alkylene, oxy-2-4C alkylene, oxy-1-3C alkylene or NR11R12; and R2-R4 : H or R1; or 2R1+C, 2R2+C, 2R3+C, 2R4+C : 3-6C cycloalkyl; or R1+R2+R3+R4 : cyclic group with 3-10 ring atoms, preferably carbocyclyl (contains 1-3 N, S and/or O) or spirocyclyl with 3-10 ring atoms, preferably carbocyclyl (contains 2-3 N, S and/or O, both saturated or partially unsaturated and both optionally substituted by G); R5 : 1-20C alkylene, oxy-2-4C alkylene, oxy-1-3C alkylene (all optionally substituted by G), H, 3-20C cycloalkyl, 1-20C (halo)alkyl, 1-20C (halo)alkenyl, 1-20C (halo)alkynyl, 3-20C cycloalkylthio, 3-20C cycloalkenyl, 3-20C cycloalkenyl-oxy, 3-20C cycloalkenyl-thio or SiR11R12R13; R11-R13 : hydrocarbyl (optionally substituted by 1-30C moiety, preferably 1-20C moiety) or H; R6 : 1-20C alkylene, oxy-2-4C alkylene, oxy-1-3C alkylene (all optionally substituted by G), H, 2-20C alkyl, 3-20C cycloalkyl, 1-20C haloalkyl, 1-20C (halo)alkenyl, 1-20C (halo)alkynyl, 3-20C cycloalkyloxy, 3-20C cycloalkylthio or 3-20C cycloalkenyl; R7 : 1-20C alkylene, oxy-2-4C alkylene, oxy-1-3C alkylene (all optionally substituted by G), H, 3-20C cycloalkyl, 1-20C (halo)alkyl, 1-20C (halo)alkenyl, 1-20C (halo)alkynyl, 3-20C cycloalkenyl, 3-20C cycloalkenyl-oxy or SiR11R12R13; either R8 : H, 1-20C cycloalkyl, halo, 1-20C alkenyl, 1-20C alkynyl, 1-20C (halo)alkyl, 1-20C cyanoalkyl, 3-20C cycloalkylalkyl, aryl-1-20C alkyl, heteroaryl-1-20C alkyl, 1-20C alkylcarbonyl, 1-20C alkoxycarbonyl, 1-20C alkenyloxy-carbonyl, 1-20C alkenyl-alkyloxy-carbonyl, aryl-1-20C alkyloxy-carbonyl, 3-20C cycloalkoxycarbonyl, 3-20C cycloalkyloxy-carbonyl, 1-20C alkylsulfonyl, arylsulfonyl, 3-20C cycloalkylsulfonyl, 1-20C alkylsulfinyl, arylsulfinyl, 1-20C 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, 3-20C cycloalkyl, halo, 1-20C (halo)alkyl, 1-20C alkynyl, 1-20C alkenyl, 1-20C cyanoalkyl, aryl-1-20C alkyl, heteroaryl-1-20C alkyl, 1-20C alkylcarbonyl, 1-20C alkoxycarbonyl, 1-20C alkylsulfonyl, arylsulfonyl, 3-20C cycloalkylsulfonyl, 1-20C alkylsulfinyl, arylsulfinyl, 3-20C cycloalkylsulfinyl, 1-20C alkoxycarbonyl-1-20C alkyl; or R8+R9 : sulfilimine moiety, amidine moiety (both optionally substituted) or iminophosphorane moiety; and G : halo, OH, 1-4C alkoxy or 1-4C alkylthio. An independent claim is also included for a spray solution for treating plants, preferably for increasing tolerance to abiotic stress, comprising (I) or their salts. ACTIVITY : Plant protectant. The ability of (I) to increase cold stress tolerance in plants was tested in Zea mays. The results showed that (Z)-1-Ethoxy-3,6,7-trimethyl-oct-2-en-4-yne-1,6-diol 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.