Diterpenoid compounds imparting stress resistance to plants

A composition, comprising a compound having the following structure:

• wherein, in the formula:
• X is selected from the group consisting of hydroxy, substituted hydroxy, halogen, thiol, and substituted thiol;
• one of Y1 and Y2 is hydrogen or alkyl, and the other is Z-W, wherein Z is a single bond, or a divalent group having alkane or substituted alkane having two hydrogen atoms removed, and W is hydroxy, substituted hydroxy, aldehyde, carboxyl, or substituted carboxyl;
• and
• R1-R24 are independently selected from the group of hydrogen, alkyl, and substituted alkyl.

A composition for imparting stress resistance to a plant or augmenting said stress resistance, comprising a compound having the following structure:

• wherein, in the formula:
• X is selected from the group consisting of hydroxy, substituted hydroxy, halogen, thiol, and substituted thiol;
• one of Y1 and Y2 is hydrogen or alkyl, and the other is Z-W, wherein Z is a single bond, or a divalent group having alkane or substituted alkane having two hydrogen atoms removed, and W is hydroxy, substituted hydroxy, aldehyde, carboxyl, or substituted carboxyl;
• and
• R1-R24 are independently selected from the group of hydrogen, alkyl, and substituted alkyl.

A method of imparting stress resistance to a plant or augmenting said stress resistance, wherein said method comprises the following steps:

• a) applying to said plant a compound having the following structure:
• wherein, in the formula:
• X is selected from the group consisting of hydroxy, substituted hydroxy, halogen, thiol, and substituted thiol;
• one of Y1 and Y2 is hydrogen or alkyl, and the other is Z-W, wherein Z is a single bond, or a divalent group having alkane or substituted alkane having two hydrogen atoms removed, and W is hydroxy, substituted hydroxy, aldehyde, carboxyl, or substituted carboxyl;
• and
• R1-R24 are independently selected from the group of hydrogen, alkyl, and substituted alkyl.

A method of producing stress resistant plants, comprising:

• a) applying to said plant a compound having the following structure:
• wherein, in the formula:
• X is selected from the group consisting of hydroxy, substituted hydroxy, halogen, thiol, and substituted thiol;
• one of Y1 and Y2 is hydrogen or alkyl, and the other is Z-W, wherein Z is a single bond, or a divalent group having alkane or substituted alkane having two hydrogen atoms removed, and W is hydroxy, substituted hydroxy, aldehyde, carboxyl, or substituted carboxyl;
• and
• R1-R24 are independently selected from the group of hydrogen, alkyl, and substituted alkyl.

A method of producing stress resistant plant tissues, comprising:

• a) applying to said plant tissue a compound having the following structure:
• wherein, in the formula:
• X is selected from the group consisting of hydroxy, substituted hydroxy, halogen, thiol, and substituted thiol;
• one of Y1 and Y2 is hydrogen or alkyl, and the other is Z-W, wherein Z is a single bond, or a divalent group having alkane or substituted alkane having two hydrogen atoms removed, and W is hydroxy, substituted hydroxy, aldehyde, carboxyl, or substituted carboxyl;
• and
• R1-R24 are independently selected from the group of hydrogen, alkyl, and substituted alkyl.

A method of producing stress resistant plant cells, comprising:

• a) applying to said plant cell a compound having the following structure:
• wherein, in the formula:
• X is selected from the group consisting of hydroxy, substituted hydroxy, halogen, thiol, and substituted thiol;
• one of Y1 and Y2 is hydrogen or alkyl, and the other is Z-W, wherein Z is a single bond, or a divalent group having alkane or substituted alkane having two hydrogen atoms removed, and W is hydroxy, substituted hydroxy, aldehyde, carboxyl, or substituted carboxyl;
• and
• R1-R24 are independently selected from the group of hydrogen, alkyl, and substituted alkyl.

A method of producing stress resistant plant seeds, comprising:

• a) applying to said plant a compound having the following structure:
• wherein, in the formula:
• X is selected from the group consisting of hydroxy, substituted hydroxy, halogen, thiol, and substituted thiol;
• one of Y1 and Y2 is hydrogen or alkyl, and the other is Z-W, wherein Z is a single bond, or a divalent group having alkane or substituted alkane having two hydrogen atoms removed, and W is hydroxy, substituted hydroxy, aldehyde, carboxyl, or substituted carboxyl;
• and
• R1-R24 are independently selected from the group of hydrogen, alkyl, and substituted alkyl;
• and
• b) obtaining said seed from said plant.

A method of synthesizing a compound having the following structure:

• wherein, in the formula:
• X is selected from the group consisting of hydroxy, substituted hydroxy, halogen, thiol, and substituted thiol;
• one of Y1 and Y2 is hydrogen or alkyl, and the other is Z-W, wherein Z is a single bond, or a divalent group having alkane or substituted alkane having two hydrogen atoms removed, and W is hydroxy, substituted hydroxy, aldehyde, carboxyl, or substituted carboxyl;
• and
• R1-R24 are independently selected from the group of hydrogen, alkyl, and substituted alkyl, said method comprises the following steps:
• a) reacting a compound (an intermediate 1) having
• wherein, in the formula:
• R5-R24 are independently selected from the group consisting of hydrogen, alkyl, and substituted alkyl, and the same as R1-R24 for WAF, with an alkyl lithium to provide an intermediate 2;
• b) mixing and reacting the product obtained in a) with m-chloroperbenzoic acid and then with a 10% potassium hydroxide in methanol to provide an intermediate 4;
• c) reacting the product obtained in b) with N-methylmorphorine N-oxide in the presence of tetrapropyl ammonium peruthenate to provide an intermediate 5;
• d) adding a compound
• wherein, one of V1 and V2 is hydrogen or alkyl, and the other is Z-V, and wherein Z is (CH2)n-C(═O)—O—, V is alkyl, n is an integer of 0 or more, and R is alkyl, to said intermediate 5 obtained in the step c) in an organic solvent in the presence of NaNH2 to provide an intermediate (6):
• e) adding diisobutyl aluminum hydride in an organic solvent to said intermediate (6) obtained in the step d) to provide
• wherein, X is selected from the group consisting of hydroxy, substituted hydroxy, halogen, thiol, and substituted thiol;
• one of U1 and U2 is hydrogen or alkyl, and the other is Z-U, wherein Z is a single bond, or a divalent group having alkane or substituted alkane having two hydrogen atoms removed, and U is hydroxy;
• and
• R1-R24 are independently selected from the group of hydrogen, alkyl, and substituted alkyl;
• and optionally
• a further oxidation or substitution step where Y1 is other than hydroxy.

A method of quantifying a compound having the following structure:

• wherein, in the formula:
• X is selected from the group consisting of hydroxy, substituted hydroxy, halogen, thiol, and substituted thiol;
• one of Y1 and Y2 is hydrogen or alkyl, and the other is Z-W, wherein Z is a single band, or a divalent group having alkane or substituted alkane having two hydrogen atoms removed, and W is hydroxy, substituted hydroxy, aldehyde, carboxyl, or substituted carboxyl;
• and
• R1-R24 are independently selected from the group of hydrogen, alkyl, and substituted alkyl, said method comprises the following steps:
• 1) providing a sample;
• 2) adding the predetermined amount of the steric isomer of said compound to said sample;
• 3) separating said sample by a reverse phase liquid chromatography;
• and
• 4) calculating the amount of said compound from said separated steric isomer.

A composition for inducing a rapid accumulation of a WRKY family gene in a plant under a condition requiring the accumulation of a WRKY family gene, said composition comprises a compound having the following structure:

• wherein, in the formula:
• X is selected from the group consisting of hydroxy, substituted hydroxy, halogen, thiol, and substituted thiol;
• one of Y1 and Y2 is hydrogen or alkyl, and the other is Z-W, wherein Z is a single bond, or a divalent group having alkane or substituted alkane having two hydrogen atoms removed, and W is hydroxy, substituted hydroxy, aldehyde, carboxyl, or substituted carboxyl;
• and
• R1 R24 are independently selected from the group of hydrogen, alkyl, and substituted alkyl.

A composition for regulating the expression of a WRKY family gene, comprising a compound having the following structure:

• wherein, in the formula:
• X is selected from the group consisting of hydroxy, substituted hydroxy, halogen, thiol, and substituted thiol;
• one of Y1 and Y2 is hydrogen or alkyl, and the other is Z-W, wherein Z is a single bond, or a divalent group having alkane or substituted alkane having two hydrogen atoms removed, and W is hydroxy, substituted hydroxy, aldehyde, carboxyl, or substituted carboxyl;
• and
• R1-R24 are independently selected from the group of hydrogen, alkyl, and substituted alkyl.

A method of inducing a rapid accumulation of a WRKY family gene in a plant under a condition requiring the accumulation of a WRKY family gene, wherein said method comprises the following steps:

• a) applying to said plant a compound having the following structure:
• wherein, in the formula:
• X is selected from the group consisting of hydroxy, substituted hydroxy, halogen, thiol, and substituted thiol;
• one of Y1 and Y2 is hydrogen or alkyl, and the other is Z-W, wherein Z is a single bond, or a divalent group having alkane or substituted alkane having two hydrogen atoms removed, and W is hydroxy, substituted hydroxy, aldehyde, carboxyl, or substituted carboxyl;
• and
• R1-R24 are independently selected from the group of hydrogen, alkyl, and substituted alkyl.

A composition for facilitating the elongating growth or auxetic growth of a plant, inhibiting the elongating growth of a plant, facilitating the maturation of a plant, or regulating the flowering of a plant, said composition comprises a compound having the following structure:

• wherein, in the formula:
• X is selected from the group consisting of hydroxy, substituted hydroxy, halogen, thiol, and substituted thiol;
• one of Y1 and Y2 is hydrogen or alkyl, and the other is Z-W, wherein Z is a single bond, or a divalent group having alkane or substituted alkane having two hydrogen atoms removed, and W is hydroxy, substituted hydroxy, aldehyde, carboxyl, or substituted carboxyl;
• and
• R1-R24 are independently selected from the group of hydrogen, alkyl, and substituted alkyl.

A method of facilitating the elongating growth or auxetic growth of a plant, inhibiting the elongating growth of a plant, facilitating the maturation of a plant, or regulating the flowering of a plant, said method comprises applying to a plant a compound having the following structure:

• wherein, in the formula:
• X is selected from the group consisting of hydroxy, substituted hydroxy, halogen, thiol, and substituted thiol;
• one of Y1 and Y2 is hydrogen or alkyl, and the other is Z-W, wherein Z is a single bond, or a divalent group having alkane or substituted alkane having two hydrogen atoms removed, and W is hydroxy, substituted hydroxy, aldehyde, carboxyl, or substituted carboxyl;
• and
• R1-R24 are independently selected from the group of hydrogen, alkyl, and substituted alkyl.