Precursor compounds for molecular coatings

A method of protecting an agricultural product, comprising:

• providing a solution comprising a composition dissolved in a solvent, the composition comprising:
• one or more compounds of Formula II:
• and one or more compounds of Formula I:
• wherein the composition comprises at least 90% by mass of the one or more compounds of Formula II and the one or more compounds of Formula I, and for both Formula I and Formula II:
• each Ra is independently —H or —C1-C6 alkyl;
• each Rb is independently selected from —H, —C1-C6 alkyl, or —OH;
• R1, R2, R5, R6, R9, R10, R11, R12and R13 are each independently, at each occurrence, —H, —OR14, —NR14R15, —SR14, halogen, —C1-C6 alkyl, —C2-C6 alkenyl, —C2-C6 alkynyl, —C3-C7 cycloalkyl, aryl, or heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with one or more —OR14, —NR14R15, —SR14, or halogen;
• R3, R4, R7, and R8 are each independently, at each occurrence, —H, —OR14, —NR14R15, —SR14, halogen, —C1-C6 alkyl, —C2-C6 alkenyl, —C2-C6 alkynyl, —C3-C7 cycloalkyl, aryl, or heteroaryl wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with one or more —OR14, —NR14R15, —SR14, or halogen;
• or
• R3 and R4 can combine with the carbon atoms to which they are attached to form a C3-C6 cycloalkyl, a C4-C6 cycloalkenyl, or 3- to 6-membered ring heterocycle;
• and/or
• R7 and R8 can combine with the carbon atoms to which they are attached to form a C3-C6 cycloalkyl, a C4-C6 cycloalkenyl, or 3- to 6-membered ring heterocycle;
• R14 and R15 are each independently, at each occurrence, —H, —C1-C6 alkyl, —C2-C6 alkenyl, or —C2-C6 alkynyl;
• the symbol represents a single bond or a cis or trans double bond;
• n is 0, 1, 2, 3, 4, 5, 6, 7 or 8;
• m is 0, 1, 2 or 3;
• q is 0, 1, 2, 3, 4 or 5;
• and
• r is 0, 1, 2, 3, 4, 5, 6, 7 or 8, and
• wherein the composition optionally comprises one or more additives selected from fatty acids, esters, and organic salts;
• applying the solution to a surface of the agricultural product;
• and
• removing the solvent to form a protective coating on the agricultural product, the coating having a thickness of less than 3 microns.

A method of protecting an agricultural product, comprising:

• providing a mixture comprising a composition in a solvent, the composition comprising:
• one or more compounds of Formula II:
• and one or more compounds of Formula I:
• wherein the composition comprises at least 90% by mass of the one or more compounds of Formula II and the one or more compounds of Formula I, and for both Formula I and Formula II:
• each Ra is independently —H or —C1-C6 alkyl;
• each Rb is independently selected from —H, —C1-C6 alkyl, or —OH;
• R1, R2, R5, R6, R9, R10, R11, R12 and R13 are each independently, at each occurrence, —H, —OR14, —NR14R15, —SR14, halogen, —C1-C6 alkyl, —C2-C6 alkenyl, —C2-C6 alkynyl, —C3-C7cycloalkyl, aryl, or heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with one or more —OR14, —NR14R15, —SR14, or halogen;
• R3, R4, R7, and R8 are each independently, at each occurrence, —H, —OR14, —NR14R15, —SR14, halogen, —C1-C6 alkyl, —C2-C6 alkenyl, —C2-C6 alkynyl, —C3-C7 cycloalkyl, aryl, or heteroaryl wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with one or more —OR14, —NR14R15, —SR14, or halogen;
• or
• R3 and R4 can combine with the carbon atoms to which they are attached to form a C3-C6 cycloalkyl, a C4-C6cycloalkenyl, or 3- to 6-membered ring heterocycle;
• and/or
• R7 and R8 can combine with the carbon atoms to which they are attached to form a C3-C6 cycloalkyl, a C4-C6cycloalkenyl, or 3- to 6-membered ring heterocycle;
• R14 and R15 are each independently, at each occurrence, —H, —C1-C6 alkyl, —C2-C6 alkenyl, or —C2-C6 alkynyl;
• the symbol represents a single bond or a cis or trans double bond;
• n is 0, 1, 2, 3, 4, 5, 6, 7 or 8;
• m is 0, 1, 2 or 3;
• q is 0, 1, 2, 3, 4 or 5;
• and
• r is 0, 1, 2, 3, 4, 5, 6, 7 or 8, and
• wherein the composition optionally comprises one or more additives selected from fatty acids, esters, amides, amines, thiols, carboxylic acids, ethers, aliphatic waxes, alcohols, organic salts, and inorganic salts;
• and
• causing the mixture to be applied to a surface of the agricultural product to form a coating on the agricultural product.

A method of protecting an agricultural product, comprising:

• providing a mixture comprising a composition in a solvent, wherein the composition comprises:
• one or more compounds of Formula II:
• and optionally one or more compounds of Formula I:
• wherein the composition comprises at least 90% by mass of the one or more compounds of Formula II and the one or more compounds of Formula I, and for both Formula I and Formula II:
• each Ra is independently —H or —C1-C6 alkyl;
• each Rb is independently selected from —H, -C1-C6 alkyl, or —OH;
• R1, R2, R5, R6, R9, R10, R11, R12and R13 are each independently, at each occurrence, —H, —OR14, —NR14R15, —SR14, halogen, —C1-C6 alkyl, —C2-C6 alkenyl, —C2-C6 alkynyl, —C3-C7 cycloalkyl, aryl, or heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with one or more —OR14, —NR14R15, —SR14, or halogen;
• R3, R4, R7, and R8 are each independently, at each occurrence, —H, —OR14, —NR14R15, —SR14, halogen, —C1-C6 alkyl, —C2-C6alkenyl, —C2-C6 alkynyl, —C3-C7 cycloalkyl, aryl, or heteroaryl wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with one or more —OR14, —NR14R15, —SR14, or halogen;
• or
• R3 and R4 can combine with the carbon atoms to which they are attached to form a C3-C6 cycloalkyl, a C4-C6cycloalkenyl, or 3- to 6-membered ring heterocycle;
• and/or
• R7 and R8 can combine with the carbon atoms to which they are attached to form a C3-C6 cycloalkyl, a C4-C6_cycloalkenyl, or 3- to 6-membered ring heterocycle;
• R14 and R15 are each independently, at each occurrence, —H, —C1-C6 alkyl, —C2-C6 alkenyl, or —C2-C6 alkynyl;
• the symbol represents a single bond or a cis or trans double bond;
• n is 0, 1, 2, 3, 4, 5, 6, 7 or 8;
• m is 0, 1, 2 or 3;
• q is 0, 1, 2, 3, 4 or 5;
• and
• r is 0, 1, 2, 3, 4, 5, 6, 7 or 8;
• wherein the composition optionally further comprises one or more additives selected from fatty acids, esters, amides, amines, thiols, carboxylic acids, ethers, aliphatic waxes, alcohols, organic salts, and inorganic salts;
• applying the solution to a surface of the agricultural product;
• and
• removing the solvent to form a coating on the agricultural product.