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BR-112021014592-B1 - PHOTOSENSITIZING COMPOUNDS, MANUFACTURING METHODS AND APPLICATION IN PLANTS

BR112021014592B1BR 112021014592 B1BR112021014592 B1BR 112021014592B1BR-112021014592-B1

Abstract

PHOTOSENSITIZING COMPOUNDS, METHODS OF MANUFACTURE AND APPLICATION IN PLANTS. Compounds of general Formula I are provided herein: Formula I or agriculturally acceptable salts thereof. Compounds of Formula I can be used to improve plant health. For example, compounds of Formula I can be used to inhibit a microbial pathogen in a plant or to increase a plant's resistance to one or more abiotic stresses. Methods for manufacturing compounds of general Formula I, as well as synthetic intermediates, are also provided.

Inventors

  • Michael Fefer
  • Jun Liu
  • Kenneth Ng
  • Yuichi Terazono
  • Brady Nash
  • INNA TESHLER
  • WENZI CKURSHUMOVA
  • MICHAEL A. BROOK
  • Yang Chen

Assignees

  • SUNCOR ENERGY INC

Dates

Publication Date
20260310
Application Date
20200124
Priority Date
20190125

Claims (16)

  1. 1. Compound of Formula I: or an agriculturally acceptable salt thereof characterized in that: Z1 is OR1-; Z2 is NR2-(CH2)n-NR4R5, NR2-(CH2)n-N+R4R5R6Y-, NR2-(CH2)n-O(PO3H)-W+, NR2-(CH2)n-Si(R7)3, NR2-(CH2)n-SR8 or NR2-(CH2)n-NR4-(CH2)p-NR9R10; eZ3 is OR12 or Z3 = Z2, each R1, R2 and R12 is independently H or C1-C20 alkyl; each R4, R6, R9 and R10 is independently H or C1-C20 alkyl; R8 is -(CH2)q-(CH2CH2O)m-R13; R5 is C1-C20 alkyl; R7 is O (trisubstituted silyl), wherein trisubstituted silyl refers to a silyl group that is independently substituted by three functional groups selected from C1-C20 alkyl; R13 is H; 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 1 to 16; m is an integer selected from 1 to 100; each Ra, Rb, Rc, Rd, Re and Rf is independently C1-C20 alkyl or C2-C20 alkenyl; It is a single bond or a double bond; It is a single bond or a double bond; and M is 2H or some kind of metal.
  2. 2. Compound according to claim 1, characterized in that it is represented by Formula I-A1 or an agriculturally acceptable salt thereof.
  3. 3. A compound according to claim 1 or 2, or an agriculturally acceptable salt thereof, characterized in that: Ra, Rc, Re and Rf are methyl; Rb is vinyl and Rd is ethyl.
  4. 4. A compound according to any one of claims 1 to 3, or an agriculturally acceptable salt thereof, characterized in that M is a metal species selected from the group consisting of Cu(II), Co(II), Fe(II), Mn(II), Mg(II), Zn(II), Pd(II), Sn(IV), Al(III), Pt(II), Si(IV), Ge(IV), Ga(III) and In(III).
  5. 5. A compound according to any one of claims 1 to 4, or an agriculturally acceptable salt thereof, characterized in that R1 is H; R2 is H; R4 is H or C1-C20 alkyl; R5 is C1-C20 alkyl; R6 is C1-C20 alkyl; R7 is O (trisubstituted silyl), wherein trisubstituted silyl refers to a silyl group that is independently substituted by three functional groups selected from C1-C20 alkyl; R8 is -(CH2)q-(CH2CH2O)m-R13; R9 is C1-C20 alkyl; R10 is C1-C20 alkyl; R12 is H; R13 is H; n is an integer selected from 2 to 4; p is an integer selected from 2 to 4; and em is an integer selected from 1 to 20.
  6. 6. Compound according to claim 1, characterized in that it is: or an agriculturally acceptable salt thereof.
  7. 7. Composition characterized in that it comprises: at least one compound, as defined in any one of claims 1 to 6, or an agriculturally acceptable salt thereof; and a carrier fluid.
  8. 8. Composition according to claim 7, characterized in that it further comprises a chelating agent comprising at least one carboxylic acid group or an agriculturally acceptable salt thereof, optionally selected from the group consisting of ethylenediaminetetraacetic acid (EDTA) or an agriculturally acceptable salt thereof, ethylenediamine-N,N'-disuccinic acid (EDDS) or an agriculturally acceptable salt thereof, iminodisuccinic acid (IDS) or an agriculturally acceptable salt thereof, and mixtures thereof.
  9. 9. Composition according to claim 7 or 8, characterized in that it further comprises a surfactant, optionally selected from the group consisting of an ethoxylated alcohol, a polymeric surfactant, a fatty acid ester, a poly(ethylene glycol), an ethoxylated alkyl alcohol, a monoglyceride, an alkyl monoglyceride and a mixture thereof.
  10. 10. Composition, according to any one of claims 7 to 9, characterized in that it further comprises an oil selected from the group consisting of a mineral oil, an essential oil, a vegetable oil and a mixture thereof.
  11. 11. Composition, according to any one of claims 7 to 10, characterized in that the carrier fluid comprises water or an oil-in-water emulsion.
  12. 12. A method for promoting plant health, characterized in that it comprises: applying to the plant the compound, of the type defined in any one of claims 1 to 6, or an agriculturally acceptable salt thereof, or the composition, of the type defined in any one of claims 7 to 11; and exposing the plant to light.
  13. 13. Method according to claim 12, characterized in that promoting plant health comprises preventing or inhibiting the growth of a plant microbial pathogen.
  14. 14. Method, according to claim 12, characterized in that promoting plant health comprises increasing the plant's resistance to one or more abiotic stresses.
  15. 15. Method according to claim 12, characterized in that promoting plant health comprises controlling a plant pest, wherein the plant pest is selected from the group consisting of insects and insect larvae.
  16. 16. Method, according to any one of claims 12 to 15, characterized in that the plant is a non-woody crop plant, a woody plant or a grass.

Description

RELATED REQUEST [001] This application claims priority over Provisional Application No. U.S. 62/796,981 filed January 25, 2019, the contents of which are incorporated herein by reference for all purposes. FIELD [002] The technical field generally refers to tetrapyrrole photosensitizing compounds and their use to promote plant health. More particularly, the technical field refers to modified e6 Chlorine compounds and their use for the photodynamic inhibition of microbial pathogens, such as fungal or bacterial pathogens, in plants. Modified e6 Chlorine compounds can also be used to increase resistance or tolerance to abiotic stress in plants and/or as insecticides to protect plants from plant pests. BACKGROUND [003] Photodynamic inhibition of microbial pathogens involves exposing a photosensitive agent to light to generate reactive oxygen species (ROS), such as singlet oxygen, which can have detrimental effects on microbial pathogens. Existing photodynamic inhibition techniques and applications have several shortcomings. SUMMARY [004] In one aspect of the present description, a compound of Formula I is provided: [005] or an agriculturally acceptable salt thereof, for use in promoting the health of a plant, [006] where: [007] each Z1, Z2 and Z3 is, independently, OR1 or NR2R3; [008] each R1, R2 and R3 is independently H, alkyl, substituted alkyl, aryl, substituted aryl, alkenyl, substituted alkenyl, alkynyl or substituted alkynyl, wherein if Z1, Z2 and Z3 are each OR1, then at least one R1 is not H and if Z1, Z2 and Z3 are each NR2R3, then at least one R3 is not H; [009] each Ra, Rb, Rc, Rd, Re and Rf is, independently, H, H, alkyl, substituted alkyl, aryl, substituted aryl, alkenyl, substituted alkenyl, alkynyl or substituted alkynyl; [0010] It is a single bond or a double bond; [0011] is it a single bond or a double bond and [0012] M is 2H or a type of metal, [0013] wherein the substituted alkyl, substituted aryl, substituted alkenyl and substituted alkynyl groups are independently substituted by one or more -X, -RB, -O-, =O, -ORB, -SRB, -S-, -NRB2, Si(RC)3, -N+RB3, -NRB-(Alk)-NRB2, -NRB-(Alk)-N+RB3, -NRB-(Alk)-ORB, -NRB-(Alk)-OP(=O)(ORB)(O-), -NRB-(Alk)-OP(=O)(ORB)2, -NRB-(Alk)-Si(RC)3, -NRB-(Alk)-SRB, -O-(Alk)-NRB2, -O-(Alk)-N+RB3, -O-(Alk)-ORB, -O-(Alk)-OP(=O)(ORB)(O-), -O-(Alk)-OP(=O)(ORB)2, - O-(Alk)-Si(RC)3, -O-(Alk)-SRB,=NRB, -CX3, -CN, -OCN, -SCN, -N=C=O, -NCS, -NO, -NO2, =N2, -N3, -NHC(=O)RB, -OC(=O)RB, -NHC(=O)NRB2, -S(=O)2-, -S(=O)2OH, -S(= O)2RB, -OS(=O)2ORB, -S(=O)2NRB2, -S(=O)RB, -OP(=O)(ORB)(O-), -OP(=O)(ORB)2, -P(=O)(ORB)2, -P(=O)(O-)2, -P(=O)(OH)2, -P(O)(ORB)(O-), -C( =O)RB, -C(=O)X, -C(S)RB, -C(O)ORB, -C(O)O-, -C(S)ORB, -C(O)SRB, -C(S)SRB, -C(O)NRB2, -C(S)NRB2 or -C(=NRB)NRB2; [0014] each X is independently a halogen: F, Cl, Br or I; [0015] each RB is independently H, alkyl, aryl, arylalkyl, a heterocycle, an alkyloxy group, such as poly(ethyleneoxy), PEG or poly(methyleneoxy), an encapsulated poly(ethyleneoxy), encapsulated PEG or encapsulated polymethyleneoxy or a protecting group; [0016] the encapsulated poly(ethyleneoxy), encapsulated PEG and encapsulated poly(methylenoxy) groups each being independently encapsulated with alkyl, aryl, arylalkyl, alkenyl, alkynyl, CO(alkyl), CO(aryl), CO(arylalkyl), CO(alkenyl) or CO(alkynyl); [0017] each RC is independently alkyl, aryl, arylalkyl, O(alkyl), O(aryl), O(arylalkyl) or O(silyl trisubstituted); [0018] each trisubstituted silyl is independently substituted by three functional groups selected from alkyl, alkenyl, alkynyl, aryl and arylalkyl and [0019] each Alky is, independently, alkylene, alkenylene or alkynylene. [0020] In another aspect of the present description, a compound of Formula I is provided: [0021] or an agriculturally acceptable salt thereof, for use in promoting the health of a plant, [0022] where: [0023] Z1 is OR1; [0024] 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, OR3, 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 [0025] the other of Z2 and Z3 is OR12; [0026] or [0027] 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, OR3, 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 [0028] Z3 = Z2; [0029] each R1, R2, R4, R6, R8, R9, R10, R11 a