Use of substituted 1-(aryl ethynyl)-, 1-(heteroaryl ethynyl)-, 1-(heterocyclyl ethynyl)- and 1-(cycloalkenyl ethynyl)-cyclohexanols as active agents against abiotic plant stress

A compound comprising a substituted 1-(arylethynyl)-, 1-(heteroarylethynyl)-, 1-(heterocyclylethynyl)- and 1-(cycloalkenylethynyl)cyclohexanols of formula (I) and/or salt thereof,

• capable of being used for increasing stress tolerance in plants to abiotic stress and/or for increasing plant yield,
• where
• [X-Y] represents the moieties
• Q represents the moieties Q-1 to Q-6
• where R7, R8, R9, R10, R11, R12, R13, R14, R17, R18, R19, R20, R22, R23, R24, R25, R26, R28, R29 and R30 and A1 to A9 each have the meaning according to the definitions below and where the arrow represents a bond to the respective moiety C—R6 in formula (I),
• R1 represents alkyl, cycloalkyl, cycloalkenyl, alkenyl, alkynyl, alkenylalkyl, alkynylalkyl, alkoxyalkyl, hydroxyalkyl, haloalkyl, haloalkenyl, haloalkynyl, haloalkoxyalkyl, alkoxyhaloalkyl, halo alkoxyhaloalkyl, alkylthioalkyl, haloalkylthioalkyl, aryl, heteroaryl, heterocyclyl,
• R2, R3 and R4 independently of one another represent hydrogen, halogen, alkyl, cycloalkyl, cycloalkenyl, alkenyl, alkynyl, alkenylalkyl, alkynylalkyl, alkoxyalkyl, hydroxyalkyl, haloalkyl, haloalkenyl, haloalkynyl, haloalkoxyalkyl, alkoxyhaloalkyl, halo alkoxyhaloalkyl, alkylthioalkyl, haloalkylthioalkyl, aryl, heteroaryl, heterocyclyl,
• R5 represents hydroxy, alkoxy, aryloxy, cycloalkyloxy, alkenyloxy, alkenylalkyloxy, alkoxyalkyloxy, alkylcarbonyloxy, arylcarbonyloxy, heteroarylcarbonyloxy, cycloalkylcarbonyloxy, alkoxycarbonyloxy, allyloxycarbonyloxy, aryloxyalkyloxy, arylalkyloxy, alkoxyalkoxyalkyloxy, alkylthioalkyloxy, trialkylsilyloxy, alkyl(bisalkyl)silyloxy, alkyl(bisaryl)silyloxy, aryl(bisalkyl)silyloxy, cycloalkyl(bisalkyl)silyloxy, halo(bisalkyl)silyloxy, trialkylsilylalkoxyalkyloxy,
• R6 represents nitro, amino, hydroxy, hydrothio, thiocyanato, isothiocyanato, halogen, alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, arylalkynyl, trialkylsilylalkynyl, aryl, arylalkyl, arylalkoxy, heteroaryl, haloalkyl, halocycloalkyl, haloalkenyl, alkoxy, haloalkoxy, aryloxy, heteroaryloxy, cycloalkyloxy, cycloalkylalkoxy, alkenyloxy, alkynylalkyloxy, hydroxyalkyl, alkoxyalkyl, aryloxyalkyl, heteroaryloxyalkyl, alkylthio, haloalkylthio, alkoxycarbonylalkylthio, arylthio, cycloalkylthio, heteroarylthio, alkylthioalkyl, alkylamino, bisalkylamino, alkenylamino, cycloalkylamino, alkylcarbonylamino, cycloalkylcarbonylamino, arylcarbonylamino, heteroarylcarbonylamino, formylamino, haloalkylcarbonylamino, alkoxycarbonylamino, alkylaminocarbonylamino, alkyl(alkyl)aminocarbonylamino, alkylsulfonylamino, cycloalkylsulfonylamino, arylsulfonylamino, hetarylsulfonylamino, sulfonylhaloalkylamino, aminoalkylsulfonyl, aminohaloalkylsulfonyl, alkylaminosulfonyl, aminosulfonyl, bisalkylaminosulfonyl, cycloalkylaminosulfonyl, haloalkylaminosulfonyl, heteroarylaminosulfonyl, arylaminosulfonyl, arylalkylaminosulfonyl, alkylsulfonyl, cycloalkylsulfonyl, arylsulfonyl, alkylsulfinyl, cycloalkylsulfinyl, arylsulfinyl, N,S-dialkylsulfonimidoyl, S-alkylsulfonimidoyl, alkylsulfonylaminocarbonyl, cycloalkylsulfonylaminocarbonyl, arylalkylcarbonylamino, cycloalkylalkylcarbonylamino, heteroarylcarbonylamino, alkoxyalkylcarbonylamino, hydroxyalkylcarbonylamino, alkoxycarbonylaminoalkylcarbonylamino, cyano, cyanoalkyl, hydroxycarbonyl, alkoxycarbonyl, cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, aryloxycarbonyl, arylalkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl, haloalkyloxycarbonyl, alkoxyalkoxycarbonyl, alkenyloxyalkoxycarbonyl, alkylaminoalkoxycarbonyl, trisalkylsilyloxyalkoxycarbonyl, bisalkylaminoalkoxycarbonyl, alkyl(alkyl)aminoalkoxycarbonyl, cyanoalkoxycarbonyl, heterocyclyl-N-alkoxycarbonyl, heteroaryloxycarbonyl, heteroarylalkoxycarbonyl, heterocyclylalkoxycarbonyl, heterocyclyloxycarbonyl, alkenylalkoxycarbonyl, alkynylalkoxycarbonyl, arylalkynyloxycarbonyl, arylalkenyloxycarbonyl, aminocarbonyl, alkylaminocarbonyl, bisalkylaminocarbonyl, alkyl(alkyl)aminocarbonyl, alkyl(alkoxy)aminocarbonyl, alkoxyalkylaminocarbonyl, alkenylaminocarbonyl, cycloalkylaminocarbonyl, arylaminocarbonyl, arylalkylaminocarbonyl, heteroarylalkylaminocarbonyl, cyanoalkylaminocarbonyl, haloalkylaminocarbonyl, alkynylalkylaminocarbonyl, alkoxycarbonylaminocarbonyl, arylalkoxycarbonylaminocarbonyl, hydroxycarbonylalkyl, alkoxycarbonylalkyl, cycloalkoxycarbonylalkyl, cycloalkylalkoxycarbonyl alkyl, alkenyloxycarbonylalkyl, arylalkoxycarbonylalkyl, alkylaminocarbonylalkyl, aminocarbonylalkyl, bisalkylaminocarbonylalkyl, cycloalkylaminocarbonylalkyl, arylalkylaminocarbonylalkyl, heteroarylalkylaminocarbonylalkyl, cyanoalkylaminocarbonyl alkyl, haloalkylaminocarbonylalkyl, alkynylalkylaminocarbonylalkyl, cycloalkylalkylaminocarbonylalkyl, alkoxycarbonylaminocarbonylalkyl, arylalkoxycarbonylaminocarbonylalkyl, alkoxycarbonylalkylaminocarbonyl, hydroxycarbonylalkylaminocarbonyl, arylalkoxycarbonylalkylaminocarbonyl, alkoxycarbonylheterocyclyl-N-carbonyl, alkoxycarbonylalkylheterocyclylideneaminocarbonyl, alkoxycarbonylheterocyclylidenalkylaminocarbonyl, alkoxycarbonylalkyl(alkyl)aminocarbonyl, alkoxycarbonylcycloalkylideneaminocarbonyl, heterocyclyl-N-carbonyl, aminocarbonylalkylaminocarbonyl, alkylaminocarbonylalkylaminocarbonyl, cycloalkylaminocarbonylalkylaminocarbonyl, cycloalkylalkylaminocarbonyl, cycloalkylalkylaminocarbonylalkyl, cycloalkylalkylaminocarbonylalkylaminocarbonyl, alkenylalkylaminocarbonyl, alkenylaminocarbonylalkyl, alkenylalkylaminocarbonylalkyl, alkylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, formyl, hydroxyiminomethyl, aminoiminomethyl, alkoxyiminomethyl, alkylaminoiminomethyl, dialkylaminoiminomethyl, cycloalkoxyiminomethyl, cycloalkylalkoximinomethyl, aryloximinomethyl, arylalkoxyiminomethyl, arylalkylaminoiminomethyl, alkenyloxyiminomethyl, arylaminoiminomethyl, arylsulfonylaminoiminomethyl, heteroarylalkyl, heterocyclylalkyl, hydroxycarbonylheterocyclyl, alkoxycarbonylheterocyclyl, alkenyloxycarbonylheterocyclyl, alkenylalkoxycarbonylheterocyclyl, arylalkoxycarbonylheterocyclyl, cycloalkoxycarbonylheterocyclyl, cycloalkylalkoxycarbonylheterocyclyl, aminocarbonylheterocyclyl, alkylaminocarbonylheterocyclyl, bisalkylaminocarbonylheterocyclyl, cycloalkylaminocarbonylheterocyclyl, arylalkylaminocarbonylheterocyclyl, alkenylaminocarbonylheterocyclyl, hydroxycarbonylheterocyclylalkyl, alkoxycarbonylheterocyclylalkyl, hydroxycarbonylcycloalkylalkyl, alkoxycarbonylcycloalkylalkyl, hydroxyaminocarbonyl, alkoxyaminocarbonyl, arylalkoxyaminocarbonyl, heterocyclyl, alkylcarbonyloxy, arylcarbonyloxy, heteroarylcarbonyloxy, cycloalkylcarbonyloxy, alkoxycarbonyloxy, alkenyloxycarbonyloxy,
• R7, R8, R9 and R10 independently of one another represent hydrogen, halogen, nitro, amino, cyano, alkyl, aryl, heteroaryl, cycloalkyl, cycloalkenyl, alkenyl, alkynyl, alkenylalkyl, alkynylalkyl, hydroxy, alkoxy, alkoxyalkoxy, alkoxyalkyl, hydroxyalkyl, haloalkoxy, haloalkyl, haloalkenyl, haloalkynyl, haloalkoxyalkyl, alkoxyhaloalkyl, haloalkoxyhaloalkyl, hydrothio, alkylthio, haloalkylthio, alkylthioalkyl, haloalkylthioalkyl, alkylamino, bisalkylamino, alkenylamino, cycloalkylamino, alkylcarbonylamino, cycloalkylcarbonylamino, arylcarbonylamino, heteroarylcarbonylamino, formylamino, haloalkylcarbonylamino, alkoxycarbonylamino, alkylaminocarbonylamino, (alkyl)aminocarbonylamino, alkylsulfonylamino, cycloalkylsulfonylamino, arylsulfonylamino, hetarylsulfonylamino, sulfonylhaloalkylamino, aminoalkylsulfonyl, aminohaloalkylsulfonyl, alkylaminosulfonyl, bisalkylaminosulfonyl, cycloalkylaminosulfonyl, haloalkylaminosulfonyl, heteroarylaminosulfonyl, arylaminosulfonyl, arylalkylaminosulfonyl, alkylsulfonyl, cycloalkylsulfonyl, arylsulfonyl, hydroxycarbonyl, alkoxycarbonyl, cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, aryloxycarbonyl, arylalkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl, aminocarbonyl, alkylaminocarbonyl, bisalkylaminocarbonyl, alkyl(alkyl)aminocarbonyl, alkyl(alkoxy)aminocarbonyl, alkenylaminocarbonyl, cycloalkylaminocarbonyl, arylaminocarbonyl, arylalkylaminocarbonyl,
• A1, A2, A3 and A4 are identical or different and independently of one another represent N (nitrogen) or the moieties C—H, C—CH3, C—F, C—Cl, C—Br, C—I, C—OCF3, C—OCH3, C—CF3, C—CO2H, C—CO2CH3 where, however, in no case more than two nitrogen atoms are adjacent to one another,
• R11 and R12 independently of one another represent hydrogen, halogen, alkyl, aryl, heteroaryl, heterocyclyl, cycloalkyl, alkenyl, alkynyl, alkoxy, alkoxyalkyl, aryloxyalkyl, haloalkoxy, haloalkyl, haloalkoxyalkyl, alkoxyhaloalkyl, haloalkoxyhaloalkyl, alkylthio, haloalkylthio, alkylthioalkyl, hydroxycarbonyl, alkoxycarbonyl, cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, aryloxycarbonyl, arylalkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl, aminocarbonyl, alkylaminocarbonyl, bisalkylaminocarbonyl, alkyl(alkyl)aminocarbonyl, alkyl(alkoxy)aminocarbonyl, alkenylaminocarbonyl, cycloalkylaminocarbonyl, arylaminocarbonyl, arylalkylaminocarbonyl, cycloalkylthio, heterocyclylthio, alkylsulfinyl, arylsulfinyl, heteroarylsulfinyl, cycloalkylsulfinyl, heterocyclylsulfinyl, alkylsulfonyl, arylsylfonyl, heteroarylsulfonyl, cycloalkylsulfonyl, heterocyclylsulfonyl,
• A5 represents S (sulfur), O (oxygen) or the moieties N—H, N—CH3, N—CH2CH3, N—CH(CH3)2, N—CO2t-Bu, N-aryl, N-heteroaryl, N-heterocyclyl,
• R13, R14, R17 and R18 independently of one another represent hydrogen, alkyl, halogen, cycloalkyl, aryl, heteroaryl, heterocyclyl, alkenyl, alkynyl, alkenylalkyl, arylalkyl, alkoxy, alkoxyalkoxy, alkoxyalkyl, hydroxy, haloalkyl, haloalkylthio, alkylthio, arylthio, cycloalkylthio, heterocyclylthio, alkylsulfinyl, arylsulfinyl, heteroarylsulfinyl, cycloalkylsulfinyl, heterocyclylsulfinyl, alkylsulfonyl, arylsulfonyl, heteroarylsulfonyl, cycloalkylsulfonyl, heterocyclylsulfonyl or
• R13 and R17 with the atoms to which they are attached form a fully saturated or partially saturated 5- to 7-membered ring which is optionally substituted further,
• A6, A7 are identical or different and independently of one another represent O (oxygen), S (sulfur), S═O, S(═O)2, N—H, N+—CH3(—O−), N—OCH3, N—CH3 or the moiety CR15R16 where, however, in no case two oxygen or sulfur atoms are adjacent to one another, and where R15 and R16 in the moiety CR15R16 each have identical or different meanings according to the definition below and
• R15 and R16 independently of one another represent hydrogen, halogen, alkyl, aryl, heteroaryl, heterocyclyl, cycloalkyl, alkenyl, alkoxy, alkoxyalkyl, aryloxyalkyl, haloalkoxy, haloalkyl, haloalkoxyalkyl, alkoxyhaloalkyl, haloalkoxyhaloalkyl, alkylthio, haloalkylthio, alkylthioalkyl, hydroxycarbonyl, alkoxycarbonyl, cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, aryloxycarbonyl, arylalkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl, aminocarbonyl, alkylaminocarbonyl, bisalkylaminocarbonyl, alkyl(alkyl)aminocarbonyl, alkyl(alkoxy)aminocarbonyl, alkenylaminocarbonyl, cycloalkylaminocarbonyl, arylaminocarbonyl, arylalkylaminocarbonyl, amino, alkylamino, cycloalkylamino, bisalkylamino, arylthio, cycloalkylthio, heterocyclylthio, alkylsulfinyl, arylsulfinyl, heteroarylsulfinyl, cycloalkylsulfinyl, heterocyclylsulfinyl, alkylsulfonyl, arylsulfonyl, heteroarylsulfonyl, cycloalkylsulfonyl, heterocyclylsulfonyl,
• R19, R20, R22 and R23 independently of one another represent hydrogen, alkyl, halogen, cycloalkyl, aryl, heteroaryl, heterocyclyl, alkenyl, alkynyl, arylalkyl, heterocyclylalkyl, alkoxy, alkoxyalkoxy, alkoxyalkyl, haloalkyl, alkylthio, arylthio, cycloalkylthio, heterocyclylthio, alkylsulfinyl, arylsulfinyl, heteroarylsulfinyl, cycloalkylsulfinyl, heterocyclylsulfinyl, alkylsulfonyl, arylsulfonyl, heteroarylsulfonyl, cycloalkylsulfonyl, heterocyclylsulfonyl,
• A8 represents O (oxygen), S (sulfur), S═O, S(═O)2, N—H, N+—CH3(—O−), N—CH3, N—OCH3 or the moiety CHR21 and where R21 in the moiety CHR21 has the meaning according to the definition below,
• R21 represents hydrogen, halogen, alkyl, aryl, heteroaryl, heterocyclyl, cycloalkyl, alkenyl, alkynyl, heterocyclylalkyl, alkoxy, alkoxyalkyl, aryloxyalkyl, haloalkoxy, haloalkyl, alkoxyhaloalkyl, haloalkoxyhaloalkyl, alkylthio, haloalkylthio, alkylthioalkyl, hydroxycarbonyl, alkoxycarbonyl, cycloalkoxycarbonyl, arylalkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl, aminocarbonyl, alkylaminocarbonyl, bisalkylaminocarbonyl, alkyl(alkyl)aminocarbonyl, alkyl(alkoxy)aminocarbonyl, alkenylaminocarbonyl, cycloalkylaminocarbonyl, arylaminocarbonyl, arylalkylaminocarbonyl, amino, alkylamino, cycloalkylamino, bisalkylamino, arylthio, cycloalkylthio, heterocyclylthio, alkylsulfinyl, arylsulfinyl, heteroarylsulfinyl, cycloalkylsulfinyl, heterocyclylsulfinyl, alkylsulfonyl, arylsulfonyl, heteroarylsulfonyl, cycloalkylsulfonyl, heterocyclylsulfonyl,
• R24, R25, R26, R28, R29 and R30 independently of one another represent hydrogen, alkyl, halogen, cycloalkyl, aryl, heteroaryl, heterocyclyl, alkenyl, alkoxy, alkoxyalkoxy, alkoxyalkyl, haloalkyl, alkylthio, haloalkylthio, arylthio, cycloalkylthio, heterocyclylthio, alkylsulfinyl, arylsulfinyl, heteroarylsulfinyl, cycloalkylsulfinyl, heterocyclylsulfinyl, alkylsulfonyl, arylsulfonyl, heteroarylsulfonyl, cycloalkylsulfonyl, heterocyclylsulfonyl,
• A9 represents O (oxygen), S (sulfur), S═O, S(═O)2, N—H, N+—CH3(—O−), N—CH3, N—OCH3 or the moiety CHR27 and where R27 in the moiety CHR27 has the meaning according to the definition below and
• R27 represents hydrogen, halogen, alkyl, aryl, heteroaryl, heterocyclyl, cycloalkyl, alkenyl, alkoxy, alkoxyalkyl, aryloxyalkyl, haloalkoxy, haloalkyl, alkylthio, haloalkylthio, hydroxycarbonyl, alkoxycarbonyl, cycloalkoxycarbonyl, arylalkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl, aminocarbonyl, alkylaminocarbonyl, bisalkylaminocarbonyl, alkyl(alkyl)aminocarbonyl, alkyl(alkoxy)aminocarbonyl, alkenylaminocarbonyl, cycloalkylaminocarbonyl, arylaminocarbonyl, arylalkylaminocarbonyl, amino, alkylamino, cycloalkylamino, bisalkylamino, arylthio, cycloalkylthio, heterocyclylthio, alkylsulfinyl, arylsulfinyl, heteroarylsulfinyl, cycloalkylsulfinyl, heterocyclylsulfinyl, alkylsulfonyl, arylsulfonyl, heteroarylsulfonyl, cycloalkylsulfonyl, heterocyclylsulfonyl.