# US 2014/0155479 A1 · Tiglien-3-one derivatives

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- Number: US 2014/0155479 A1
- Document ID: US20140155479A1
- Status: Published application
- Kind: A1
- Application number: 14/084,949
- Filed: 2013-11-20
- Published: 2014-06-05
- Earliest claimed: 2005-12-23
- Assignees: QBiotics Limited
- Applicants: QBiotics Limited
- Inventors: Paul Warren Reddell; Victoria Anne Gordon
- Web page: https://patentgrep.com/patent/US20140155479A1

## CPC

- A61K 31/336: having three-membered rings, e.g. oxirane, fumagillin
- A01N 43/20: three- or four-membered rings
- A01N 43/90: having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
- A01N 45/00: Biocides, pest repellants or attractants, or plant growth regulators, containing compounds having three or more carbocyclic rings condensed among themselves, at least one ring not being a six-membered ring (halogenated hydrocarbons A01N29/08; condensed with heterocyclic rings A01N43/00)
- A01N 53/00: Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
- A61K 9/0014: {Skin, i.e. galenical aspects of topical compositions (non-active ingredients are additionally classified in A61K47/00; A61K9/0009, A61K9/0021, A61K9/7015, A61K9/7023 take precedence; cosmetic preparations A61K8/00, A61Q; preparations for wound dressings or bandages A61L26/00)}
- A61K 9/0019: {Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner (non-active ingredients are additionally classified in A61K47/00)}
- A61K 9/06: Ointments; Bases therefor; {Other semi-solid forms, e.g. creams, sticks, gels (composition of ointments, creams or gels A61K47/00)}
- A61K 47/10: Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
- A61P 31/00: Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P 31/04: Antibacterial agents
- A61P 33/00: Antiparasitic agents
- A61P 33/02: Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- A61P 35/00: Antineoplastic agents
- A61P 35/02: specific for leukemia
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D 301/32: Separation; Purification
- C07D 303/14: by free hydroxyl radicals
- C07D 303/17: containing oxirane rings condensed with carbocyclic ring systems having three or more relevant rings
- C07D 303/32: by aldehydo- or ketonic radicals
- C07D 303/44: Esterified with oxirane-containing hydroxy compounds
- C07D 493/04: Ortho-condensed systems
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

The present invention relates to tiglien-3-one compounds and their use in methods of treating or preventing protozoal infections, bacterial infections, parasitic infections and cell proliferative disorders. The tiglien-3-one compounds are also used in methods of controlling pests in humans, animals, plants and the environment.

## Claims

### Claim at position 1

1-24. (canceled)

### Claim 25

A method of treating or preventing a cell proliferative disorder comprising administering to a subject a compound of formula (II):
wherein:
X is selected from —O—, —S— and —NR25—;
R1 and R2 are independently selected from hydrogen, —OH, —OC1-C10 alkyl, —OC2-C10 alkenyl, —OC2-C10 alkynyl, -Ocycloalkyl, —OC(O)C1-C10 alkyl, —OC(O)C2-C10 alkenyl, —OC(O)C2-C10 alkynyl, —OC(O)cycloalkyl, —OC(O)heterocyclyl, —OC(O)heteroaryl, —OC(O)NHC1-C10 alkyl, —OC(O)NHC2-C10 alkenyl, —OC(O)NHC2-C10 alkynyl, —OC(O)NHcycloalkyl, —OC(O)NHaryl, —OC(O)NHheterocyclyl, —OC(O)NHheteroaryl, —OC(S)NHC1-C10 alkyl, —OC(S)NHC2-C10 alkenyl, —OC(S)NHC2-C10 alkynyl, —OC(S)NHcycloalkyl, —OC(S)NHaryl, —OC(S)NHheterocyclyl, —OC(S)NHheteroaryl or R1 and R2 taken together are ≡O, ═S, ═NH or ═N(C1-C6 alkyl);
R3 is hydrogen, —C1-C10 alkyl, —C2-C10 alkenyl or —C2-C10 alkynyl;
R4 and R5 are each hydrogen, —C1-C10 alkyl, —C2-C10 alkenyl, —C2-C10 alkynyl, —OH, —OC1-C10 alkyl, —OC2-C10 alkenyl, —OC2-C10 alkynyl, -Ocycloalkyl, —OC(O)C1-C10 alkyl, —OC(O)C2-C10 alkenyl, —OC(O)C2-C10 alkynyl, —OC(O)cycloalkyl, —OC(O)aryl, —OC(O)heterocyclyl, —OC(O)heteroaryl, —OC(O)NHC1-C10 alkyl, —OC(O)NHC2-C10 alkenyl, —OC(O)NHC2-C10 alkynyl, —OC(O)NHcycloalkyl, —OC(O)NHaryl, —OC(O)NHheterocyclyl, —OC(O)NHheteroaryl, —OC(S)NHC1-C10 alkyl, —OC(S)NHC2-C10 alkenyl, —OC(S)NHC2-C10 alkynyl, —OC(S)NHcycloalkyl, —OC(S)NHaryl, —OC(S)NHheterocyclyl, —OC(S)NHheteroaryl, F, Cl, Br, I, —CN, —NO2 or N(R25)2, or R4 and R5 taken together form a double bond or are —O—, —S—, —NR25— or —CR26R27—;
R6 is selected from hydrogen, —C1-C10 alkyl, —C2-C10 alkenyl and —C2-C10 alkynyl;
R8 is selected from hydrogen, —C1-C10 alkyl, —C2-C10 alkenyl and —C2-C10 alkynyl;
R10 is selected from hydrogen, —C1-C10 alkyl, —C2-C10 alkenyl and —C2-C10 alkynyl;
R11 is selected from —OH, —OC1-C20 alkyl, —OC2-C20 alkenyl, —OC2-C20 alkynyl, -Ocycloalkyl, —OC(O)C1-C20 alkyl, —OC(O)C2-C20 alkenyl, —OC(O)C2-C20 alkynyl, —OC(O)cycloalkyl, —OC(O)aryl, —OC(O)heterocyclyl, —OC(O)heteroaryl, —OC(O)NHC1-C20 alkyl, —OC(O)NHC2-C20 alkenyl, —OC(O)NHC2-C20 alkynyl, —OC(O)NHcycloalkyl, —OC(O)NHaryl, —OC(O)NHheterocyclyl, —OC(O)NHheteroaryl, —OC(S)NHC1-C20 alkyl, —OC(S)NHC2-C20 alkenyl, —OC(S)NHC2-C20 alkynyl, —OC(S)NHcycloalkyl, —OC(S)NHaryl, —OC(S)NHheterocyclyl, —OC(S)NHheteroaryl or R10 and R11 taken together form a carbonyl group (═O);
R12 is selected from —OH, —OC1-C20 alkyl, —OC2-C20 alkenyl, —OC2-C20 alkynyl, -Ocycloalkyl, —OC(O)C1-C20 alkyl, —OC(O)C2-C20 alkenyl, —OC(O)C2-C20 alkynyl, —OC(O)cycloalkyl, —OC(O)aryl, —OC(O)heterocyclyl, —OC(O)heteroaryl, —OC(O)NHC1-C20 alkyl, —OC(O)NHC2-C20 alkenyl, —OC(O)NHC2-C20 alkynyl, —OC(O)NHcycloalkyl, —OC(O)NHaryl, —OC(O)NHheterocyclyl, —OC(O)NHheteroaryl, —OC(S)NHC1-C20 alkyl, —OC(S)NHC2-C20 alkenyl, —OC(S)NHC2-C20 alkynyl, —OC(S)NHcycloalkyl, —OC(S)NHaryl, —OC(S)NHheterocyclyl, —OC(S)NHheteroaryl;
R13 and R14 are independently selected from hydrogen and —C1-C10 alkyl;
R18 is selected from C1-C20 alkyl, —C2-C20 alkenyl, —C2-C20 alkynyl, —OH, —OC1-C20 alkyl, —OC2-C20 alkenyl, —OC2-C20 alkynyl, -Ocycloalkyl, —OC(O)C1-C20 alkyl, —OC(O)C2-C20 alkenyl, —OC(O)C2-C20 alkynyl, —OC(O)cycloalkyl, —OC(O)aryl, —OC(O)heterocyclyl, —OC(O)heteroaryl, —NHC1-C20 alkyl, —NHC2-C20 alkenyl, —NHC2-C20 alkynyl, —NHcycloalkyl, —NHaryl, —NHheterocyclyl, —NHheteroaryl, —OC(O)NHC1-C20 alkyl, —OC(O)NHC2-C20 alkenyl, —OC(O)NHC2-C20 alkynyl, —OC(O)NHcycloalkyl, —OC(O)NHaryl, —OC(O)NHheterocyclyl, —OC(O)NHheteroaryl, —OC(S)NHC1-C20 alkyl, —OC(S)NHC2-C20 alkenyl, —OC(S)NHC2-C20 alkynyl, —OC(S)NHcycloalkyl, —OC(S)NHaryl, —OC(S)NHheterocyclyl, —OC(S)NHheteroaryl;
R19 and R20 are independently selected from hydrogen, —C1-C6 alkyl, —C2-C6 alkenyl, —C2-C20 alkynyl, —OH, —OC1-C6 alkyl, —OC2-C6 alkenyl, —OC2-C6 alkynyl, -Ocycloalkyl, —OC(O)C1-C6 alkyl, —OC(O)C2-C6 alkenyl, —OC(O)C2-C6 alkynyl, —OC(O)cycloalkyl, —OC(O)aryl, —OC(O)heterocyclyl, —OC(O)heteroaryl or R19 and R20 taken together form a carbonyl or thiocarbonyl group;
R21 is selected from hydrogen, —C1-C10 alkyl, —C2-C10 alkenyl and —C2-C10 alkynyl;
R22 is selected from —OH, —OC1-C20 alkyl, —OC2-C20 alkenyl, —OC2-C20 alkynyl, -Ocycloalkyl, —OC(O)C1-C20 alkyl, —OC(O)C2-C20 alkenyl, —OC(O)C2-C20 alkynyl, —OC(O)cycloalkyl, —OC(O)aryl, —OC(O)heterocyclyl, —OC(O)heteroaryl, —OC(O)NHC1-C20 alkyl, —OC(O)NHC2-C20 alkenyl, —OC(O)NHC2-C20 alkynyl, —OC(O)NHcycloalkyl, —OC(O)NHaryl, —OC(O)NHheterocyclyl, —OC(O)NHheteroaryl, —OC(S)NHC1-C20 alkyl, —OC(S)NHC2-C20 alkenyl, —OC(S)NHC2-C20 alkynyl, —OC(S)NHcycloalkyl, —OC(S)NHaryl, —OC(S)NHheterocyclyl, —OC(S)NHheteroaryl or R21 and R22 taken together form a carbonyl group;
R23 is selected from hydrogen, —OH, —OC1-C20 alkyl, —OC2-C20 alkenyl, —OC2-C20 alkynyl, -Ocycloalkyl, —OC(O)C1-C20 alkyl, —OC(O)C2-C20 alkenyl, —OC(O)C2-C20 alkynyl, —OC(O)cycloalkyl, —OC(O)aryl, —OC(O)heterocyclyl, —OC(O)heteroaryl, —OC(O)NHC1-C20 alkyl, —OC(O)NHC2-C20 alkenyl, —OC(O)NHC2-C20 alkynyl, —OC(O)NHcycloalkyl, —OC(O)NHaryl, —OC(O)NHheterocyclyl, —OC(O)NHheteroaryl, —OC(S)NHC1-C20 alkyl, —OC(S)NHC2-C20 alkenyl, —OC(S)NHC2-C20 alkynyl, —OC(S)NHcycloalkyl, —OC(S)NHaryl, —OC(S)NHheterocyclyl, —OC(S)NHheteroaryl;
R24 is selected from hydrogen, —OH, —OC1-C20 alkyl, —OC2-C20 alkenyl, —OC2-C20 alkynyl, -Ocycloalkyl, —OC(O)C1-C20 alkyl, —OC(O)C2-C20 alkenyl, —OC(O)C2-C20 alkynyl, —OC(O)cycloalkyl, —OC(O)aryl, —OC(O)heterocyclyl, —OC(O)heteroaryl, —OC(O)NHC1-C20 alkyl, —OC(O)NHC2-C20 alkenyl, —OC(O)NHC2-C20 alkynyl, —OC(O)NHcycloalkyl, —OC(O)NHaryl, —OC(O)NHheterocyclyl, —OC(O)NHheteroaryl, —OC(S)NHC1-C20 alkyl, —OC(S)NHC2-C20 alkenyl, —OC(S)NHC2-C20 alkynyl, —OC(S)NHcycloalkyl, —OC(S)NHaryl, —OC(S)NHheterocyclyl, —OC(S)NHheteroaryl;
R25 is selected from hydrogen and —C1-C10 alkyl;
R26 and R27 are independently selected from hydrogen, —C1-C10 alkyl, —OH, —OC1-C10 alkyl;
wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heterocyclyl and heteroaryl is optionally substituted;
and geometric isomers or stereoisomers thereof and a pharmaceutically acceptable salt thereof.

### Claim 26 (depends on 25)

The method according to claim 25, wherein the compound is a compound of formula (III):
wherein:
R3 is hydrogen, —C1-C6 alkyl or —C2-C6 alkenyl;
R4 and R5 are each independently hydrogen, —C1-C6 alkyl, —C2-C6 alkenyl, —OH, —OC1-C6 alkyl, —OC2-C6 alkenyl, —OC(O)C1-C6 alkyl, —OC(O)C2-C6 alkenyl, —OC(O)aryl, —OC(O)heterocyclyl, —OC(O)heteroaryl, F, Cl, Br or I, or R4 and R5 taken together form a double bond or are —O—;
R6 is hydrogen, —C1-C6 alkyl or —C2-C6 alkenyl;
R8 is hydrogen, —C1-C6 alkyl or —C2-C6 alkenyl;
R13 and R14 are each independently hydrogen or —C1-C6 alkyl;
Ra is selected from hydrogen, —C1-C20 alkyl, —C2-C20 alkenyl, —C2-C2o alkynyl, —C(O)C2-C20 alkyl, —C(O)C2-C20 alkenyl, —OC(O)C2-C20 alkynyl, —C(O)cycloalkyl, —C(O)aryl, —C(O)heterocyclyl, —C(O)heteroaryl, —C(O)NHC1-C20 alkyl, —C(O)NHC2-C20 alkenyl, —C(O)NHC2-C20 alkynyl, —C(O)NHcycloalkyl, —C(O)NHaryl, —C(O)NHheterocyclyl, —C(O)NHheteroaryl, —C(S)NHC1-C20 alkyl, —C(S)NHC2-C20 alkenyl, —C(S)NHC2-C20 alkynyl, —C(S)NHcycloalkyl, —C(S)NHaryl, —C(S)NHheterocyclyl and —C(S)NHheteroaryl;
Rb, Rc, Rd, Re and Rf are each independently selected from hydrogen, —C1-C20 alkyl, —C2-C20 alkenyl, —C2-C20 alkynyl, —C(O)C1-C20 alkyl, —C(O)C2-C20 alkenyl, —OC(O)C2-C20 alkynyl, —C(O)cycloalkyl, —C(O)aryl, —C(O)heterocyclyl, —C(O)heteroaryl, —C(O)NHC1-C20 alkyl, —C(O)NHC2-C20 alkenyl, —C(O)NHC2-C20 alkynyl, —C(O)NHcycloalkyl, —C(O)NHaryl, —C(O)NHheterocyclyl, —C(O)NHheteroaryl, —C(S)NHC1-C20 alkyl, —C(S)NHC2-C20 alkenyl, —C(S)NHC2-C20 alkynyl, —C(S)NHcycloalkyl, —C(S)NHaryl, —C(S)NHheterocyclyl and —C(S)NHheteroaryl;
wherein each alkyl, alkenyl, aryl, heterocyclyl and heteroaryl group is optionally substituted;
or geometric isomers or stereoisomers and pharmaceutically, agriculturally or pesticidally acceptable salts thereof.

### Claim 27 (depends on 25)

The method according to claim 25, wherein the compound is a compound of formula (IV):
wherein:
R3 is hydrogen, —C1-C6 alkyl or —C2-C6 alkenyl;
R4 and R5 are each independently hydrogen, —C1-C6 alkyl, —C2-C6 alkenyl, —OH, —OC1-C6 alkyl, —OC2-C6 alkenyl, —OC(O)C1-C6 alkyl, —OC(O)C2-C6 alkenyl, —OC(O)aryl, —OC(O)heterocyclyl, —OC(O)heteroaryl, F, Cl, Br or I, or R4 and R5 taken together form a double bond or are —O—;
R6 is hydrogen, —C1-C6 alkyl or —C2-C6 alkenyl;
R8 is hydrogen, —C1-C6 alkyl or —C2-C6 alkenyl;
R10 is hydrogen;
R11 is hydroxy, —OC1-C20 alkyl, —OC2-C20 alkenyl, —OC(O)C2-C20 alkyl, —OC(O)C2-C20 alkenyl, —OC(O)aryl, —OC(O)heterocyclyl, —OC(O)heteroaryl; or R10 and R11 taken together form a carbonyl group;
R129 is hydrogen, —C1-C20 alkyl, —C2-C20 alkenyl, —C(O)C1-C20 alkyl, —C(O)C2-C20 alkenyl, —C(O)aryl, —C(O)heterocyclyl or —C(O)heteroaryl;
R13 and R14 are each independently hydrogen or —C1-C6 alkyl;
R189 is hydrogen, —C1-C6 alkyl, —C2-C6 alkenyl, —C(O)C1-C6 alkyl, —C(O)C2-C6 alkenyl, —C(O)aryl, —C(O)heterocyclyl or —C(O)heteroaryl;
R19 and R20 are independently selected from hydrogen, —OH, —OC1-C6 alkyl, —OC2-C6 alkenyl or R19 and R20 taken together form a carbonyl group;
R21 is hydrogen;
R22 is hydroxy, —OC1-C6 alkyl, —OC2-C6 alkenyl, —OC(O)C1-C6 alkyl, —OC(O)C2-C6 alkenyl, —OC(O)aryl, —OC(O)heterocyclyl, —OC(O)heteroaryl or R21 and R22 taken together form a carbonyl group;
wherein each alkyl, alkenyl, aryl, heterocyclyl or heteroaryl is optionally substituted;
and geometric isomers or stereoisomers thereof and pharmaceutically, agriculturally or pesticidally acceptable salts thereof.

### Claim 28 (depends on 25)

The method according to claim 25 wherein R1 and R2 are independently selected from hydrogen, hydroxy, —OC1-C6 alkyl, —OC2-C6 alkenyl, —OC(O)C1-C6 alkyl or —OC(O)C2-C6 alkenyl or R1 and R2 taken together form a carbonyl group.

### Claim 29 (depends on 25)

The method according to claim 25 wherein R4 and R5 form a double bond or R4 and R5 are hydrogen or together are —O—.

### Claim 30 (depends on 25)

The method according to claim 25 wherein R8 is hydrogen or —C1-C3 alkyl.

### Claim 31 (depends on 25)

The method according to claim 25 wherein R11 is selected from hydroxy, —C1-C20 alkyloxy, —C2-C20 alkenyloxy, —OC(O)C2-C20 alkyl or —OC(O)C2-C20 alkenyl and R12 is selected from hydroxy, —C1-C20 alkyloxy, —C2-C20 alkenyloxy, —OC(O)C1-C20 alkyl or —OC(O)C2-C20 alkenyl.

### Claim 32 (depends on 25)

The method according to claim 25 wherein R13 and R14 are independently selected from hydrogen and —C1-C3 alkyl.

### Claim 33 (depends on 25)

The method according to claim 25 wherein X is —O—.

### Claim 34 (depends on 25)

The method according to claim 25 wherein R19 and R20 are hydrogen, hydroxy, —OC1-C3 alkyl, —OC2-C3 alkenyl or R19 and R20 taken together form a carbonyl group and R18 is selected from hydroxy, —OC1-C6 alkyl, —OC2-C6 alkenyl, —OC(O)C1-C6 alkyl or —OC(O)C2-C6 alkenyl.

### Claim 35 (depends on 25)

The method according to claim 25 wherein R22 is hydroxy, —OC1-C6 alkyl, —OC2-C6 alkenyl, —OC(O)C1-C6 alkyl or —OC(O)C2-C6 alkenyl.

### Claim 36 (depends on 25)

The method according to claim 25 wherein R23 and R24 are each hydroxy.

### Claim 37 (depends on 25)

The method according to claim 25 wherein the compound of formula (II) is:
(12-tigloyl-13-(2-methylbutanoyl)-6,7-epoxy-4,5,9,12,13,20-hexahydroxy-1-tigliaen-3-one);
(12,13-di-(2-methylbutanoyl)-6,7-epoxy-4,5,9,12,13,20-hexahydroxy-tigliaen-3-one);
12-(dodeca-2,4,6-trienoyl)-13-(2-methylbutanoyl)-6,7-epoxy-4,5,9,12,13,20-hexahydroxy-1-tigliaen-3-one;
12-(deca-2,4-dienoyl)-6,7-epoxy-4,5,9,12,13,20-hexahydroxy-1-tigliaen-3-one;
12,13-di-(2-methylbutanoyl)-1, 2-2H-1,2,6,7-diepoxy-6-carboxy-4,5,9,12,13-pentahydroxy-tigliaen-3-one; and
12,13-di-(2-methylbutanoyl)-5,20-di-acetoyl-4,5,9,12,13,20-hexahydroxy-tigliaen-3-one.

### Claim 38

A method of treating or preventing a bacterial, parasitic or protozoan infection comprising administering to a subject a compound of formula (II):
wherein:
X is selected from —O—, —S— and —NR25—;
R1 and R2 are independently selected from hydrogen, —OH, —OC1-C10 alkyl, —OC2-C10 alkenyl, —OC2-C10 alkynyl, -Ocycloalkyl, —OC(O)C1-C10 alkyl, —OC(O)C2-C10 alkenyl, —OC(O)C2-C10 alkynyl, —OC(O)cycloalkyl, —OC(O)heterocyclyl, —OC(O)heteroaryl, —OC(O)NHC1-C10 alkyl, —OC(O)NHC2-C10 alkenyl, —OC(O)NHC2-C10 alkynyl, —OC(O)NHcycloalkyl, —OC(O)NHaryl, —OC(O)NHheterocyclyl, —OC(O)NHheteroaryl, —OC(S)NHC1-C10 alkyl, —OC(S)NHC2-C10 alkenyl, —OC(S)NHC2-C10 alkynyl, —OC(S)NHcycloalkyl, —OC(S)NHaryl, —OC(S)NHheterocyclyl, —OC(S)NHheteroaryl or R1 and R2 taken together are ═O, ═S, ═NH or ═N(C1-C6 alkyl);
R3 is hydrogen, —C1-C10 alkyl, —C2-C10 alkenyl or —C2-C10 alkynyl;
R4 and R5 are each hydrogen, —C1-C10 alkyl, —C2-C10 alkenyl, —C2-C10 alkynyl, —OH, —OC1-C10 alkyl, —OC2-C10 alkenyl, —OC2-C10 alkynyl, -Ocycloalkyl, —OC(O)C1-C10 alkyl, —OC(O)C2-C10 alkenyl, —OC(O)C2-C10 alkynyl, —OC(O)cycloalkyl, —OC(O)aryl, —OC(O)heterocyclyl, —OC(O)heteroaryl, —OC(O)NHC1-C10 alkyl, —OC(O)NHC2-C10 alkenyl, —OC(O)NHC2-C10 alkynyl, —OC(O)NHcycloalkyl, —OC(O)NHaryl, —OC(O)NHheterocyclyl, —OC(O)NHheteroaryl, —OC(S)NHC1-C10 alkyl, —OC(S)NHC2-C10 alkenyl, —OC(S)NHC2-C10 alkynyl, —OC(S)NHcycloalkyl, —OC(S)NHaryl, —OC(S)NHheterocyclyl, —OC(S)NHheteroaryl, F, Cl, Br, I, —CN, —NO2 or N(R25)2, or R4 and R5 taken together form a double bond or are —O—, —S—, —NR25— or —CR26R27—;
R6 is selected from hydrogen, —C1-C10 alkyl, —C2-C10 alkenyl and —C2-C10 alkynyl;
R8 is selected from hydrogen, —C1-C10 alkyl, —C2-C10 alkenyl and —C2-C10 alkynyl;
R10 is selected from hydrogen, —C1-C10 alkyl, —C2-C10 alkenyl and —C2-C10 alkynyl;
R11 is selected from —OH, —OC1-C20 alkyl, —OC2-C20 alkenyl, —OC2-C20 alkynyl, -Ocycloalkyl, —OC(O)C1-C20 alkyl, —OC(O)C2-C20 alkenyl, —OC(O)C2-C20 alkynyl, —OC(O)cycloalkyl, —OC(O)aryl, —OC(O)heterocyclyl, —OC(O)heteroaryl, —OC(O)NHC1-C20 alkyl, —OC(O)NHC2-C20 alkenyl, —OC(O)NHC2-C20 alkynyl, —OC(O)NHcycloalkyl, —OC(O)NHaryl, —OC(O)NHheterocyclyl, —OC(O)NHheteroaryl, —OC(S)NHC1-C20 alkyl, —OC(S)NHC2-C20 alkenyl, —OC(S)NHC2-C20 alkynyl, —OC(S)NHcycloalkyl, —OC(S)NHaryl, —OC(S)NHheterocyclyl, —OC(S)NHheteroaryl or R10 and R11 taken together form a carbonyl group (═O);
R12 is selected from —OH, —OC1-C20 alkyl, —OC2-C20 alkenyl, —OC2-C20 alkynyl, -Ocycloalkyl, —OC(O)C1-C20 alkyl, —OC(O)C2-C20 alkenyl, —OC(O)C2-C20 alkynyl, —OC(O)cycloalkyl, —OC(O)aryl, —OC(O)heterocyclyl, —OC(O)heteroaryl, —OC(O)NHC1-C20 alkyl, —OC(O)NHC2-C20 alkenyl, —OC(O)NHC2-C20 alkynyl, —OC(O)NHcycloalkyl, —OC(O)NHaryl, —OC(O)NHheterocyclyl, —OC(O)NHheteroaryl, —OC(S)NHC1-C20 alkyl, —OC(S)NHC2-C20 alkenyl, —OC(S)NHC2-C20 alkynyl, —OC(S)NHcycloalkyl, —OC(S)NHaryl, —OC(S)NHheterocyclyl, —OC(S)NHheteroaryl;
R13 and R14 are independently selected from hydrogen and —C1-C10 alkyl;
R18 is selected from C1-C20 alkyl, —C2-C20 alkenyl, —C2-C20 alkynyl, —OH, —OC1-C20 alkyl, —OC2-C20 alkenyl, —OC2-C20 alkynyl, -Ocycloalkyl, —OC(O)C1-C20 alkyl, —OC(O)C2-C20 alkenyl, —OC(O)C2-C20 alkynyl, —OC(O)cycloalkyl, —OC(O)aryl, —OC(O)heterocyclyl, —OC(O)heteroaryl, —NHC1-C20 alkyl, —NHC2-C20 alkenyl, —NHC2-C20 alkynyl, —NHcycloalkyl, —NHaryl, —NHheterocyclyl, —NHheteroaryl, —OC(O)NHC1-C20 alkyl, —OC(O)NHC2-C20 alkenyl, —OC(O)NHC2-C20 alkynyl, —OC(O)NHcycloalkyl, —OC(O)NHaryl, —OC(O)NHheterocyclyl, —OC(O)NHheteroaryl, —OC(S)NHC1-C20 alkyl, —OC(S)NHC2-C20 alkenyl, —OC(S)NHC2-C20 alkynyl, —OC(S)NHcycloalkyl, —OC(S)NHaryl, —OC(S)NHheterocyclyl, —OC(S)NHheteroaryl;
R19 and R20 are independently selected from hydrogen, —C1-C6 alkyl, —C2-C6 alkenyl, —C2-C20 alkynyl, —OH, —OC1-C6 alkyl, —OC2-C6 alkenyl, —OC2-C6 alkynyl, -Ocycloalkyl, —OC(O)C1-C6 alkyl, —OC(O)C2-C6 alkenyl, —OC(O)C2-C6 alkynyl, —OC(O)cycloalkyl, —OC(O)aryl, —OC(O)heterocyclyl, —OC(O)heteroaryl or R19 and R20 taken together form a carbonyl or thiocarbonyl group;
R21 is selected from hydrogen, —C1-C10 alkyl, —C2-C10 alkenyl and —C2-C10 alkynyl;
R22 is selected from hydrogen, —OH, —OC1-C20 alkyl, —OC2-C20 alkenyl, —OC2-C20 alkynyl, -Ocycloalkyl, —OC(O)C1-C20 alkyl, —OC(O)C2-C20 alkenyl, —OC(O)C2-C20 alkynyl, —OC(O)cycloalkyl, —OC(O)aryl, —OC(O)heterocyclyl, —OC(O)heteroaryl, —OC(O)NHC1-C20 alkyl, —OC(O)NHC2-C20 alkenyl, —OC(O)NHC2-C20 alkynyl, —OC(O)NHcycloalkyl, —OC(O)NHaryl, —OC(O)NHheterocyclyl, —OC(O)NHheteroaryl, —OC(S)NHC1-C20 alkyl, —OC(S)NHC2-C20 alkenyl, —OC(S)NHC2-C20 alkynyl, —OC(S)NHcycloalkyl, —OC(S)NHaryl, —OC(S)NHheterocyclyl, —OC(S)NHheteroaryl or R21 and R22 taken together form a carbonyl group;
R23 is selected from hydrogen, —OH, —OC1-C20 alkyl, —OC2-C20 alkenyl, —OC2-C20 alkynyl, -Ocycloalkyl, —OC(O)C1-C20 alkyl, —OC(O)C2-C20 alkenyl, —OC(O)C2-C20 alkynyl, —OC(O)cycloalkyl, —OC(O)aryl, —OC(O)heterocyclyl, —OC(O)heteroaryl, —OC(O)NHC1-C20 alkyl, —OC(O)NHC2-C20 alkenyl, —OC(O)NHC2-C20 alkynyl, —OC(O)NHcycloalkyl, —OC(O)NHaryl, —OC(O)NHheterocyclyl, —OC(O)NHheteroaryl, —OC(S)NHC1-C20 alkyl, —OC(S)NHC2-C20 alkenyl, —OC(S)NHC2-C20 alkynyl, —OC(S)NHcycloalkyl, —OC(S)NHaryl, —OC(S)NHheterocyclyl, —OC(S)NHheteroaryl;
R24 is selected from hydrogen, —OH, —OC1-C20 alkyl, —OC2-C20 alkenyl, —OC2-C20 alkynyl, -Ocycloalkyl, —OC(O)C1-C20 alkyl, —OC(O)C2-C20 alkenyl, —OC(O)C2-C20 alkynyl, —OC(O)cycloalkyl, —OC(O)aryl, —OC(O)heterocyclyl, —OC(O)heteroaryl, —OC(O)NHC1-C20 alkyl, —OC(O)NHC2-C20 alkenyl, —OC(O)NHC2-C20 alkynyl, —OC(O)NHcycloalkyl, —OC(O)NHaryl, —OC(O)NHheterocyclyl, —OC(O)NHheteroaryl, —OC(S)NHC1-C20 alkyl, —OC(S)NHC2-C20 alkenyl, —OC(S)NHC2-C20 alkynyl, —OC(S)NHcycloalkyl, —OC(S)NHaryl, —OC(S)NHheterocyclyl, —OC(S)NHheteroaryl;
R25 is selected from hydrogen and —C1-C10 alkyl;
R26 and R27 are independently selected from hydrogen, —C1-C10 alkyl, —OH, —OC1-C10 alkyl;
wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heterocyclyl and heteroaryl is optionally substituted;
and geometric isomers or stereoisomers thereof and pharmaceutically acceptable salt thereof.

### Claim 39 (depends on 25)

A method according to claim 25 wherein the cell proliferative disorder is a leukaemia or solid tumor cancer.

### Claim 40 (depends on 39)

A method according to claim 39 wherein the solid tumor cancer is melanoma, prostate cancer, breast cancer, ovarian cancer, basal cell carcinoma, squamous cell carcinoma, fibrosarcoma, colon cancer or lung cancer or other solid tumors.

### Claim 41 (depends on 25)

A method according to claim 25, wherein the cell proliferative disorder is sarcoides.

### Claim 42 (depends on 41)

A method according to claim 41, wherein the cell proliferative disorder is equine sarcoides.

### Claim 43 (depends on 25)

A method according to claim 25, further comprising administration of an anti-inflammatory agent.

### Claim 44

A method of stimulating a localized inflammatory response comprising administering to a subject a compound of formula (II):
wherein:
X is selected from —O—, —S— and —NR25—;
R1 and R2 are independently selected from hydrogen, —OH, —OC1-C10 alkyl, —OC2-C10 alkenyl, —OC2-C10 alkynyl, -Ocycloalkyl, —OC(O)C1-C10 alkyl, —OC(O)C2-C10 alkenyl, —OC(O)C2-C10 alkynyl, —OC(O)cycloalkyl, —OC(O)heterocyclyl, —OC(O)heteroaryl, —OC(O)NHC1-C10 alkyl, —OC(O)NHC2-C10 alkenyl, —OC(O)NHC2-C10 alkynyl, —OC(O)NHcycloalkyl, —OC(O)NHaryl, —OC(O)NHheterocyclyl, —OC(O)NHheteroaryl, —OC(S)NHC1-C10 alkyl, —OC(S)NHC2-C10 alkenyl, —OC(S)NHC2-C10 alkynyl, —OC(S)NHcycloalkyl, —OC(S)NHaryl, —OC(S)NHheterocyclyl, —OC(S)NHheteroaryl or R1 and R2 taken together are ═O, ═S, ═NH or ═N(C1-C6 alkyl);
R3 is hydrogen, —C1-C10 alkyl, —C2-C10 alkenyl or —C2-C10 alkynyl;
R4 and R5 are each hydrogen, —C1-C10 alkyl, —C2-C10 alkenyl, —C2-C10 alkynyl, —OH, —OC1-C10 alkyl, —OC2-C10 alkenyl, —OC2-C10 alkynyl, -Ocycloalkyl, —OC(O)C1-C10 alkyl, —OC(O)C2-C10 alkenyl, —OC(O)C2-C10 alkynyl, —OC(O)cycloalkyl, —OC(O)aryl, —OC(O)heterocyclyl, —OC(O)heteroaryl, —OC(O)NHC1-C10 alkyl, —OC(O)NHC2-C10 alkenyl, —OC(O)NHC2-C10 alkynyl, —OC(O)NHcycloalkyl, —OC(O)NHaryl, —OC(O)NHheterocyclyl, —OC(O)NHheteroaryl, —OC(S)NHC1-C10 alkyl, —OC(S)NHC2-C10 alkenyl, —OC(S)NHC2-C10 alkynyl, —OC(S)NHcycloalkyl, —OC(S)NHaryl, —OC(S)NHheterocyclyl, —OC(S)NHheteroaryl, F, Cl, Br, I, —CN, —NO2 or N(R25)2, or R4 and R5 taken together form a double bond or are —O—, —S—, —NR25— or —CR26R27—;
R6 is selected from hydrogen, —C1-C10 alkyl, —C2-C10 alkenyl and —C2-C10 alkynyl;
R8 is selected from hydrogen, —C1-C10 alkyl, —C2-C10 alkenyl and —C2-C10 alkynyl;
R10 is selected from hydrogen, —C1-C10 alkyl, —C2-C10 alkenyl and —C2-C10 alkynyl;
R11 is selected from —OH, —OC1-C20 alkyl, —OC2-C20 alkenyl, —OC2-C20 alkynyl, -Ocycloalkyl, —OC(O)C1-C20 alkyl, —OC(O)C2-C20 alkenyl, —OC(O)C2-C20 alkynyl, —OC(O)cycloalkyl, —OC(O)aryl, —OC(O)heterocyclyl, —OC(O)heteroaryl, —OC(O)NHC1-C20 alkyl, —OC(O)NHC2-C20 alkenyl, —OC(O)NHC2-C20 alkynyl, —OC(O)NHcycloalkyl, —OC(O)NHaryl, —OC(O)NHheterocyclyl, —OC(O)NHheteroaryl, —OC(S)NHC1-C20 alkyl, —OC(S)NHC2-C20 alkenyl, —OC(S)NHC2-C20 alkynyl, —OC(S)NHcycloalkyl, —OC(S)NHaryl, —OC(S)NHheterocyclyl, —OC(S)NHheteroaryl or R10 and R11 taken together form a carbonyl group (═O);
R12 is selected from —OH, —OC1-C20 alkyl, —OC2-C20 alkenyl, —OC2-C20 alkynyl, -Ocycloalkyl, —OC(O)C1-C20 alkyl, —OC(O)C2-C20 alkenyl, —OC(O)C2-C20 alkynyl, —OC(O)cycloalkyl, —OC(O)aryl, —OC(O)heterocyclyl, —OC(O)heteroaryl, —OC(O)NHC1-C20 alkyl, —OC(O)NHC2-C20 alkenyl, —OC(O)NHC2-C20 alkynyl, —OC(O)NHcycloalkyl, —OC(O)NHaryl, —OC(O)NHheterocyclyl, —OC(O)NHheteroaryl, —OC(S)NHC1-C20 alkyl, —OC(S)NHC2-C20 alkenyl, —OC(S)NHC2-C20 alkynyl, —OC(S)NHcycloalkyl, —OC(S)NHaryl, —OC(S)NHheterocyclyl, —OC(S)NHheteroaryl;
R13 and R14 are independently selected from hydrogen and —C1-C10 alkyl;
R18 is selected from C1-C20 alkyl, —C2-C20 alkenyl, —C2-C20 alkynyl, —OH, —OC1-C20 alkyl, —OC2-C20 alkenyl, —OC2-C20 alkynyl, -Ocycloalkyl, —OC(O)C1-C20 alkyl, —OC(O)C2-C20 alkenyl, —OC(O)C2-C20 alkynyl, —OC(O)cycloalkyl, —OC(O)aryl, —OC(O)heterocyclyl, —OC(O)heteroaryl, —NHC1-C20 alkyl, —NHC2-C20 alkenyl, —NHC2-C20 alkynyl, —NHcycloalkyl, —NHaryl, —NHheterocyclyl, —NHheteroaryl, —OC(O)NHC1-C20 alkyl, —OC(O)NHC2-C20 alkenyl, —OC(O)NHC2-C20 alkynyl, —OC(O)NHcycloalkyl, —OC(O)NHaryl, —OC(O)NHheterocyclyl, —OC(O)NHheteroaryl, —OC(S)NHC1-C20 alkyl, —OC(S)NHC2-C20 alkenyl, —OC(S)NHC2-C20 alkynyl, —OC(S)NHcycloalkyl, —OC(S)NHaryl, —OC(S)NHheterocyclyl, —OC(S)NHheteroaryl;
R19 and R20 are independently selected from hydrogen, —C1-C6 alkyl, —C2-C6 alkenyl, —C2-C20 alkynyl, —OH, —OC1-C6 alkyl, —OC2-C6 alkenyl, —OC2-C6 alkynyl, -Ocycloalkyl, —OC(O)C1-C6 alkyl, —OC(O)C2-C6 alkenyl, —OC(O)C2-C6 alkynyl, —OC(O)cycloalkyl, —OC(O)aryl, —OC(O)heterocyclyl, —OC(O)heteroaryl or R19 and R20 taken together form a carbonyl or thiocarbonyl group;
R21 is selected from hydrogen, —C1-C10 alkyl, —C2-C10 alkenyl and —C2-C10 alkynyl;
R22 is selected from —OH, —OC1-C20 alkyl, —OC2-C20 alkenyl, —OC2-C20 alkynyl, -Ocycloalkyl, —OC(O)C1-C20 alkyl, —OC(O)C2-C20 alkenyl, —OC(O)C2-C20 alkynyl, —OC(O)cycloalkyl, —OC(O)aryl, —OC(O)heterocyclyl, —OC(O)heteroaryl, —OC(O)NHC1-C20 alkyl, —OC(O)NHC2-C20 alkenyl, —OC(O)NHC2-C20 alkynyl, —OC(O)NHcycloalkyl, —OC(O)NHaryl, —OC(O)NHheterocyclyl, —OC(O)NHheteroaryl, —OC(S)NHC1-C20 alkyl, —OC(S)NHC2-C20 alkenyl, —OC(S)NHC2-C20 alkynyl, —OC(S)NHcycloalkyl, —OC(S)NHaryl, —OC(S)NHheterocyclyl, —OC(S)NHheteroaryl or R21 and R22 taken together form a carbonyl group;
R23 is selected from hydrogen, —OH, —OC1-C20 alkyl, —OC2-C20 alkenyl, —OC2-C20 alkynyl, -Ocycloalkyl, —OC(O)C1-C20 alkyl, —OC(O)C2-C20 alkenyl, —OC(O)C2-C20 alkynyl, —OC(O)cycloalkyl, —OC(O)aryl, —OC(O)heterocyclyl, —OC(O)heteroaryl, —OC(O)NHC1-C20 alkyl, —OC(O)NHC2-C20 alkenyl, —OC(O)NHC2-C20 alkynyl, —OC(O)NHcycloalkyl, —OC(O)NHaryl, —OC(O)NHheterocyclyl, —OC(O)NHheteroaryl, —OC(S)NHC1-C20 alkyl, —OC(S)NHC2-C20 alkenyl, —OC(S)NHC2-C20 alkynyl, —OC(S)NHcycloalkyl, —OC(S)NHaryl, —OC(S)NHheterocyclyl, —OC(S)NHheteroaryl;
R24 is selected from hydrogen, —OH, —OC1-C20 alkyl, —OC2-C20 alkenyl, —OC2-C20 alkynyl, -Ocycloalkyl, —OC(O)C1-C20 alkyl, —OC(O)C2-C20 alkenyl, —OC(O)C2-C20 alkynyl, —OC(O)cycloalkyl, —OC(O)aryl, —OC(O)heterocyclyl, —OC(O)heteroaryl, —OC(O)NHC1-C20 alkyl, —OC(O)NHC2-C20 alkenyl, —OC(O)NHC2-C20 alkynyl, —OC(O)NHcycloalkyl, —OC(O)NHaryl, —OC(O)NHheterocyclyl, —OC(O)NHheteroaryl, —OC(S)NHC1-C20 alkyl, —OC(S)NHC2-C20 alkenyl, —OC(S)NHC2-C20 alkynyl, —OC(S)NHcycloalkyl, —OC(S)NHaryl, —OC(S)NHheterocyclyl, —OC(S)NHheteroaryl;
R25 is selected from hydrogen and —C1-C10 alkyl;
R26 and R27 are independently selected from hydrogen, —C1-C10 alkyl, —OH, —OC1-C10 alkyl;
wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heterocyclyl and heteroaryl is optionally substituted;
and geometric isomers or stereoisomers thereof and a pharmaceutically acceptable salt thereof.

### Claim 45

A method of controlling agricultural pests comprising applying an pesticidally effective amount of a compound of formula (II):
wherein:
X is selected from —O—, —S— and —NR25—;
R1 and R2 are independently selected from hydrogen, —OH, —OC1-C10 alkyl, —OC2-C10 alkenyl, —OC2-C10 alkynyl, -Ocycloalkyl, —OC(O)C1-C10 alkyl, —OC(O)C2-C10 alkenyl, —OC(O)C2-C10 alkynyl, —OC(O)cycloalkyl, —OC(O)heterocyclyl, —OC(O)heteroaryl, —OC(O)NHC1-C10 alkyl, —OC(O)NHC2-C10 alkenyl, —OC(O)NHC2-C10 alkynyl, —OC(O)NHcycloalkyl, —OC(O)NHaryl, —OC(O)NHheterocyclyl, —OC(O)NHheteroaryl, —OC(S)NHC1-C10 alkyl, —OC(S)NHC2-C10 alkenyl, —OC(S)NHC2-C10 alkynyl, —OC(S)NHcycloalkyl, —OC(S)NHaryl, —OC(S)NHheterocyclyl, —OC(S)NHheteroaryl or R1 and R2 taken together are ═O, ═S, ═NH or ═N(C1-C6 alkyl);
R3 is hydrogen, —C1-C10 alkyl, —C2-C10 alkenyl or —C2-C10 alkynyl;
R4 and R5 are each hydrogen, —C1-C10 alkyl, —C2-C10 alkenyl, —C2-C10 alkynyl, —OH, —OC1-C10 alkyl, —OC2-C10 alkenyl, —OC2-C10 alkynyl, -Ocycloalkyl, —OC(O)C1-C10 alkyl, —OC(O)C2-C10 alkenyl, —OC(O)C2-C10 alkynyl, —OC(O)cycloalkyl, —OC(O)aryl, —OC(O)heterocyclyl, —OC(O)heteroaryl, —OC(O)NHC1-C10 alkyl, —OC(O)NHC2-C10 alkenyl, —OC(O)NHC2-C10 alkynyl, —OC(O)NHcycloalkyl, —OC(O)NHaryl, —OC(O)NHheterocyclyl, —OC(O)NHheteroaryl, —OC(S)NHC1-C10 alkyl, —OC(S)NHC2-C10 alkenyl, —OC(S)NHC2-C10 alkynyl, —OC(S)NHcycloalkyl, —OC(S)NHaryl, —OC(S)NHheterocyclyl, —OC(S)NHheteroaryl, F, Cl, Br, I, —CN, —NO2 or N(R25)2, or R4 and R5 taken together form a double bond or are —O—, —S—, —NR25— or —CR26R27—;
R6 is selected from hydrogen, —C1-C10 alkyl, —C2-C10 alkenyl and —C2-C10 alkynyl;
R8 is selected from hydrogen, —C1-C10 alkyl, —C2-C10 alkenyl and —C2-C10 alkynyl;
R10 is selected from hydrogen, —C1-C10 alkyl, —C2-C10 alkenyl and —C2-C10 alkynyl;
R11 is selected from —OH, —OC1-C20 alkyl, —OC2-C20 alkenyl, —OC2-C20 alkynyl, -Ocycloalkyl, —OC(O)C1-C20 alkyl, —OC(O)C2-C20 alkenyl, —OC(O)C2-C20 alkynyl, —OC(O)cycloalkyl, —OC(O)aryl, —OC(O)heterocyclyl, —OC(O)heteroaryl, —OC(O)NHC1-C20 alkyl, —OC(O)NHC2-C20 alkenyl, —OC(O)NHC2-C20 alkynyl, —OC(O)NHcycloalkyl, —OC(O)NHaryl, —OC(O)NHheterocyclyl, —OC(O)NHheteroaryl, —OC(S)NHC1-C20 alkyl, —OC(S)NHC2-C20 alkenyl, —OC(S)NHC2-C20 alkynyl, —OC(S)NHcycloalkyl, —OC(S)NHaryl, —OC(S)NHheterocyclyl, —OC(S)NHheteroaryl or R10 and R11 taken together form a carbonyl group (═O);
R12 is selected from —OH, —OC1-C20 alkyl, —OC2-C20 alkenyl, —OC2-C20 alkynyl, -Ocycloalkyl, —OC(O)C1-C20 alkyl, —OC(O)C2-C20 alkenyl, —OC(O)C2-C20 alkynyl, —OC(O)cycloalkyl, —OC(O)aryl, —OC(O)heterocyclyl, —OC(O)heteroaryl, —OC(O)NHC1-C20 alkyl, —OC(O)NHC2-C20 alkenyl, —OC(O)NHC2-C20 alkynyl, —OC(O)NHcycloalkyl, —OC(O)NHaryl, —OC(O)NHheterocyclyl, —OC(O)NHheteroaryl, —OC(S)NHC1-C20 alkyl, —OC(S)NHC2-C20 alkenyl, —OC(S)NHC2-C20 alkynyl, —OC(S)NHcycloalkyl, —OC(S)NHaryl, —OC(S)NHheterocyclyl, —OC(S)NHheteroaryl;
R13 and R14 are independently selected from hydrogen and —C1-C10 alkyl;
R18 is selected from C1-C20 alkyl, —C2-C20 alkenyl, —C2-C20 alkynyl, —OH, —OC1-C20 alkyl, —OC2-C20 alkenyl, —OC2-C20 alkynyl, -Ocycloalkyl, —OC(O)C1-C20 alkyl, —OC(O)C2-C20 alkenyl, —OC(O)C2-C20 alkynyl, —OC(O)cycloalkyl, —OC(O)aryl, —OC(O)heterocyclyl, —OC(O)heteroaryl, —NHC1-C20 alkyl, —NHC2-C20 alkenyl, —NHC2-C20 alkynyl, —NHcycloalkyl, —NHaryl, —NHheterocyclyl, —NHheteroaryl, —OC(O)NHC1-C20 alkyl, —OC(O)NHC2-C20 alkenyl, —OC(O)NHC2-C20 alkynyl, —OC(O)NHcycloalkyl, —OC(O)NHaryl, —OC(O)NHheterocyclyl, —OC(O)NHheteroaryl, —OC(S)NHC1-C20 alkyl, —OC(S)NHC2-C20 alkenyl, —OC(S)NHC2-C20 alkynyl, —OC(S)NHcycloalkyl, —OC(S)NHaryl, —OC(S)NHheterocyclyl, —OC(S)NHheteroaryl;
R19 and R20 are independently selected from hydrogen, —C1-C6 alkyl, —C2-C6 alkenyl, —C2-C20 alkynyl, —OH, —OC1-C6 alkyl, —OC2-C6 alkenyl, —OC2-C6 alkynyl, -Ocycloalkyl, —OC(O)C1-C6 alkyl, —OC(O)C2-C6 alkenyl, —OC(O)C2-C6 alkynyl, —OC(O)cycloalkyl, —OC(O)aryl, —OC(O)heterocyclyl, —OC(O)heteroaryl or R19 and R20 taken together form a carbonyl or thiocarbonyl group;
R21 is selected from hydrogen, —C1-C10 alkyl, —C2-C10 alkenyl and —C2-C10 alkynyl;
R22 is selected from hydrogen, —OH, —OC1-C20 alkyl, —OC2-C20 alkenyl, —OC2-C20 alkynyl, -Ocycloalkyl, —OC(O)C1-C20 alkyl, —OC(O)C2-C20 alkenyl, —OC(O)C2-C20 alkynyl, —OC(O)cycloalkyl, —OC(O)aryl, —OC(O)heterocyclyl, —OC(O)heteroaryl, —OC(O)NHC1-C20 alkyl, —OC(O)NHC2-C20 alkenyl, —OC(O)NHC2-C20 alkynyl, —OC(O)NHcycloalkyl, —OC(O)NHaryl, —OC(O)NHheterocyclyl, —OC(O)NHheteroaryl, —OC(S)NHC1-C20 alkyl, —OC(S)NHC2-C20 alkenyl, —OC(S)NHC2-C20 alkynyl, —OC(S)NHcycloalkyl, —OC(S)NHaryl, —OC(S)NHheterocyclyl, —OC(S)NHheteroaryl or R21 and R22 taken together form a carbonyl group;
R23 is selected from hydrogen, —OH, —OC1-C20 alkyl, —OC2-C20 alkenyl, —OC2-C20 alkynyl, -Ocycloalkyl, —OC(O)C1-C20 alkyl, —OC(O)C2-C20 alkenyl, —OC(O)C2-C20 alkynyl, —OC(O)cycloalkyl, —OC(O)aryl, —OC(O)heterocyclyl, —OC(O)heteroaryl, —OC(O)NHC1-C20 alkyl, —OC(O)NHC2-C20 alkenyl, —OC(O)NHC2-C20 alkynyl, —OC(O)NHcycloalkyl, —OC(O)NHaryl, —OC(O)NHheterocyclyl, —OC(O)NHheteroaryl, —OC(S)NHC1-C20 alkyl, —OC(S)NHC2-C20 alkenyl, —OC(S)NHC2-C20 alkynyl, —OC(S)NHcycloalkyl, —OC(S)NHaryl, —OC(S)NHheterocyclyl, —OC(S)NHheteroaryl;
R24 is selected from hydrogen, —OH, —OC1-C20 alkyl, —OC2-C20 alkenyl, —OC2-C20 alkynyl, -Ocycloalkyl, —OC(O)C1-C20 alkyl, —OC(O)C2-C20 alkenyl, —OC(O)C2-C20 alkynyl, —OC(O)cycloalkyl, —OC(O)aryl, —OC(O)heterocyclyl, —OC(O)heteroaryl, —OC(O)NHC1-C20 alkyl, —OC(O)NHC2-C20 alkenyl, —OC(O)NHC2-C20 alkynyl, —OC(O)NHcycloalkyl, —OC(O)NHaryl, —OC(O)NHheterocyclyl, —OC(O)NHheteroaryl, —OC(S)NHC1-C20 alkyl, —OC(S)NHC2-C20 alkenyl, —OC(S)NHC2-C20 alkynyl, —OC(S)NHcycloalkyl, —OC(S)NHaryl, —OC(S)NHheterocyclyl, —OC(S)NHheteroaryl;
R25 is selected from hydrogen and —C1-C10 alkyl;
R26 and R27 are independently selected from hydrogen, —C1-C10 alkyl, —OH, —OC1-C10 alkyl;
wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heterocyclyl and heteroaryl is optionally substituted;
and geometric isomers or stereoisomers thereof or a pesticidally acceptable salt thereof, to an environment infested with a pest.