Photosensitizer compounds, methods of manufacture and application to plants

A compound of Formula I:

• or an agriculturally acceptable salt thereof,
• wherein:
• Z1 is OR1;
• one of Z2 and Z3 is NR2R3, NR2—(CH2)n—NR4R5, NR2—(CH2)n—N+R4R5R6 Y−, NR2—(CH2)n—O(PO3H)− W+, NR2—(CH2)n—Si(R7)3, NR2—(CH2)n—SR8, NR2—(CH2)n—NR4—(CH2)p—NR9R10, NR2—(CH2)n—NR4—(CH2)p—N+R9R10R11 Y−, NR2—(CH2)n—NR4—(CH2)p—O(PO3H)− W+, NR2—(CH2)n—NR4—(CH2)p—Si(R7)3, NR2—(CH2)n—NR4—(CH2)p—SR8, O(CH2)n—NR4R5, O(CH2)n—N+R4R5R6 Y−, O(CH2)n—O(PO3H)− W+, O(CH2)n—Si(R7)3, O(CH2)n—SR8, O(CH2)n—NR4—(CH2)p—NR9R10, O(CH2)n—NR4—(CH2)p—N+R9R10R11 Y−, O(CH2)n—NR4—(CH2)p—O(PO3H)− W+ or O(CH2)n—NR4—(CH2)p—Si(R7)3;
• and
• the other one of Z2 and Z3 is OR12;
• or
• Z2 is NR2R3, NR2—(CH2)n—NR4R5, NR2—(CH2)n—N+R4R5R6 Y−, NR2—(CH2)n—O(PO3H)− W+, NR2—(CH2)n—Si(R7)3, NR2—(CH2)n—SR8, NR2—(CH2)n—NR4—(CH2)p—NR9R10, NR2—(CH2)n—NR4—(CH2)p—N+R9R10R11 Y−, NR2—(CH2)n—NR4—(CH2)p—O(PO3H)− W+, NR2—(CH2)n—NR4—(CH2)p—Si(R7)3, NR2—(CH2)n—NR4—(CH2)p—SR8, O(CH2)n—NR4R5, O(CH2)n—N+R4R5R6 Y−, O(CH2)n—O(PO3H)− W+, O(CH2)n—Si(R7)3, O(CH2)n—SR8, O(CH2)n—NR4—(CH2)p—NR9R10, O(CH2)n—NR4—(CH2)p—N+R9R10R11 Y−, O(CH2)n—NR4—(CH2)p—O(PO3H)− W+ or O(CH2)n—NR4—(CH2)p—Si(R7)3;
• and
• Z3=Z2;
• each R1, R2 and R12 is, independently, H, alkyl, substituted alkyl, aryl, substituted aryl, alkenyl, substituted alkenyl, alkynyl or substituted alkynyl;
• R3 is alkyl substituted alkyl, alkenyl, substituted alkenyl, alkynyl or substituted alkynyl;
• each R4, R6, R8, R9, R10 and R11 is, independently, H, alkyl, substituted alkyl, aryl, substituted aryl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl or —(CH2)q—(CH2CH2O)m—R13;
• R5 is alkyl, substituted alkyl, aryl, substituted aryl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl or —(CH2)q—(CH2CH2O)m—R13;
• R7 is alkyl, O(alkyl) or O(tri-substituted silyl);
• R13 is H, alkyl, substituted alkyl, aryl, substituted aryl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, CO(alkyl), CO(substituted alkyl), CO(alkenyl), CO(substituted alkenyl), CO(alkynyl) or CO(substituted alkynyl);
• W+ is an agriculturally acceptable cation;
• Y− is an agriculturally acceptable anion;
• n is an integer selected from 1 to 16;
• p is an integer selected from 1 to 16;
• q is an integer selected from 0 to 16;
• m is an integer selected from 1 to 100;
• each Ra, Rb, Rc, Rd, Re and R is, independently, H, alkyl, substituted alkyl, aryl, substituted aryl, alkenyl, substituted alkenyl, alkynyl or substituted alkynyl;
• is a single bond or a double bond;
• is a single bond or a double bond;
• and
• M is 2H or a metal species,
• wherein each substituted alkyl, substituted aryl, substituted alkenyl and substituted alkynyl groups are, independently, substituted with one or more F, Cl, Br, I, CN and N3.

A compound of Formula I-C:

• or an agriculturally acceptable salt thereof,
• wherein:
• Z1 is OR1;
• Z3═OR12 and m is an integer selected from 1 to 100;
• or
• Z3═O(CH2CH2O)m—R13 and m is an integer selected from 5 to 100;
• each R1 and R12 is, independently, H, alkyl or substituted alkyl;
• R13 is H, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, CO(alkyl), CO(substituted alkyl), CO(alkenyl), CO(substituted alkenyl), CO(alkynyl) or CO(substituted alkynyl);
• each Ra, Rb, Rc, Rd, Re and R is, independently, H, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl or substituted alkynyl;
• is a single bond or a double bond;
• is a single bond or a double bond;
• and
• M is 2H or a metal species,
• wherein the substituted alkyl, substituted alkenyl and substituted alkynyl groups are, independently, substituted with one or more F, Cl, Br, I, hydroxy, CN and N3.

A compound of Formula II-A or Formula II-B:

• or a salt thereof,
• wherein:
• R17 is H or alkyl;
• each Ra, Rb, Rc, Rd, Re and Rf is, independently, H, alkyl, substituted alkyl, aryl, substituted aryl, alkenyl, substituted alkenyl, alkynyl or substituted alkynyl;
• is a single bond or a double bond;
• is a single bond or a double bond;
• and
• M is 2H or a metal species,
• wherein the substituted alkyl, substituted aryl, substituted alkenyl and substituted alkynyl groups are, independently, substituted with one or more F, Cl, Br, I, hydroxy, alkenyl, CN and N3.