US2005070576A1PendingUtilityA1
Methods and compositions for controlling pests
Priority: May 8, 2001Filed: May 8, 2002Published: Mar 31, 2005
Est. expiryMay 8, 2021(expired)· nominal 20-yr term from priority
A01N 35/06A01N 65/42A01N 65/04A01N 37/18A01N 65/10A01N 65/12A01N 65/36A01N 65/28A61K 36/61A01N 65/48A01N 35/10A01N 65/22A01N 65/08
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Claims
Abstract
The present invention is directed to pest-controlling compositions comprising as active ingredients one or more β-diones, particularly β-diketones and β-triketones, and to the use of these compositions inter alia for preventing, eradicating, destroying, repelling or mitigating harmful, annoying or undesired pests including insects, arachnids, helminths, molluscs, protozoa and viruses. The present invention is further directed to processes of preparing β-diones by de novo synthesis or from natural sources such as volatile oil-bearing plants from families including Alliaceae, Apiaceae, Asteraceae, Cannabinaceae, Lamiaceae, Pteridaceae, Myrtaceae, Myoporaceae, Proteaceae, Rutaceae and Zingiberaceae.
Claims
exact text as granted — not AI-modified1 .- 24 . (canceled)
25 . A method for controlling harmful, annoying or undesired pests, other than plants, microbes, helminths and nematodes, said method comprising exposing said pests to a pest-controlling effective amount of a composition comprising a β-dione compound represented by the general formula (I)
wherein
A is (C═O)R 1 , (C═S)R 1 , OR 2 , SR 2 , (CR 3 NR 4 R 5 ), C(R 3 ) 2 OR 2 , NR 4 R 5 , (C═N—R 4 )R 1 , N═O, N(═O) 2 , NR 4 OR 2 or SO 4 R 2 ;
R 1 is selected from H, C 1 -C 10 alkyl, C 2 -C 10 arylalkyl, C 3 -C 6 cycloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 heteroarylalkyl, C 1 -C 10 haloalkyl, C 1 -C 10 dihaloalkyl, C 2 -C 1 , trihaloalkyl, C 2 -C 10 haloalkoxy, C 1 -C 10 hydroxyalkyl, C 1 -C 10 thioalkyl and C 1 -C 10 nitroalkyl, OR 2 , SR 2 , (CR 3 NR 4 R 5 ), NR 4 R 5 , (C═N—R 4 )R, N═O, N(═O) 2 , NR 4 OR 7 or SO 4 R 7 ;
R 2 is selected from H, C 1 -C 10 alkyl, C 2 -C 10 arylalkyl, C 3 -C 6 cycloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 heteroarylalkyl, C 2 -C 10 haloalkyl, C 2 -C 10 dihaloalkyl, C 2 -C 10 trihaloalkyl, (CR 3 NR 4 R 5 ), NR 4 R 5 , (C═N—R 4 )R&, N═O, N(═O) 2 or NR 4 OR 7 ;
R 3 is selected from H, C 1 -C 10 alkyl, C 2 -C 10 arylalkyl, C 3 -C 6 cycloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 heteroarylalkyl, C 2 -C 10 haloalkyl, C 2 -C 10 dihaloalkyl, C 2 -C 10 trihaloalkyl, C 2 -C 10 haloalkoxy, OR 7 , SR 7 , (CR 8 NR 4 R 5 ), NR 4 R 5 , (C═N—R 4 )R 6 , N═O, N(═O) 2 , NR 4 OR 7 or SO 4 R 7 ;
R 4 and R 5 are independently selected from H, C 1 -C 10 alkyl, C 2 -C 10 arylalkyl, C 3 -C 6 cycloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 heteroarylalkyl, C 2 -C 10 haloalkyl, C 2 -C 10 dihaloalkyl, C 2 -C 10 trihaloalkyl, OR 7 or SR 7 ;
R 6 is selected from H, C 1 -C 10 alkyl, C 2 -C 10 arylalkyl, C 3 -C 6 cycloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 heteroarylalkyl, C 2 -C 10 haloalkyl, C 2 -C 10 dihaloalkyl, C 2 -C 10 trihaloalkyl, C 2 -C 10 haloalkoxy, OR 7 , SR 7 , (CR 8 NR 9 R 10 ), NR 9 R 10 or NR 9 OR 7 ;
R 7 is selected from H, C 1 -C 10 alkyl, C 2 -C 10 arylalkyl, C 3 -C 6 cycloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 heteroarylalkyl, C 2 -C 10 haloalkyl, C 2 -C 10 dihaloalkyl, C 2 -C 10 trihaloalkyl;
R 8 is selected from H, C 1 C 10 alkyl, C 2 -C 10 arylalkyl, C 3 -C 6 cycloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 heteroarylalkyl, C 2 -C 10 haloalkyl, C 2 -C 10 dihaloalkyl, C 2 -C 10 trihaloalkyl, OR 11 , SR 11 or NR 9 R 10 ;
R 9 and R 10 are independently selected from H, C 1 -C 10 alkyl, C 2 -C 10 arylalkyl, C 3 -C 6 cycloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 heteroarylalkyl, C 2 -C 10 haloalkyl, C 2 -C 10 dihaloalkyl, C 2 -C 10 trihaloalkyl, OR 12 or SR 12 ;
R 11 is selected from H, C 1 -C 10 alkyl, C 2 -C 10 arylalkyl, C 3 -C 6 cycloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 heteroarylalkyl, C 2 -C 10 haloalkyl, C 2 -C 10 dihaloalkyl, C 2 -C 10 trihaloalkyl;
R 12 is selected from H, C 1 -C 10 alkyl, C 2 -C 10 arylalkyl, C 3 -C 6 cycloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 heteroarylalkyl, C 2 -C 10 haloalkyl, C 2 -C 10 dihaloalkyl, C 2 -C 10 trihaloalkyl;
B is H, C 1 -C 10 alkyl, C 2 -C 10 alkenyl, aryl or heteroaryl;
X and Y are independently selected from oxygen, sulfur, —N—R 4 ; and
Q completes a 5-8-member saturated or unsaturated carbocyclic or heterocyclic ring.
26 . The method of claim 25 , wherein the compound is represented by the general formula (III)
wherein
X, Y and Z are each independently selected from oxygen, sulfur, —N—R 4 or one of C═X, C═Y or C=Z is CH 2 ;
A is (C═O)R 1 , (C═S)R 1 , OR 2 , SR 2 , (CR 3 NR 4 R 5 ), C(R 3 ) 2 OR 2 , NR 4 R 5 , (C═N—R 4 )R 1 , N═O, N(═O) 2 , NR 4 OR 2 or SO 4 R 2 ;
B is H, C 1 -C 10 alkyl, C 2 -C 10 alkenyl, aryl or heteroaryl;
C, D, E and F are each independently selected from H, C 1 -C 10 alkyl, C 3 -C 6 cycloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 haloalkyl, C 2 -C 10 dihaloalkyl, C 2 -C 10 trihaloalkyl, OR 2 , SR 2 , (CR 3 NR 4 R 5 ), NR 4 R 5 , (C═N—R 4 )R 1 , N═O, N(═O) 2 , NR 4 OR 2 , SO 4 R 2 , C 2 -C 10 1-arylalkyl, C 2 -C 10 2-arylalkyl or (C═X)R 1 ; and
R 1 is selected from H, C 1 -C 10 alkyl, C 2 -C 10 arylalkyl, C 3 -C 6 cycloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 heteroarylalkyl, C 1 -C 10 haloalkyl, C 1 -C 10 dihaloalkyl, C 2 -C 10 trihaloalkyl, C 2 -C 10 haloalkoxy, C 1 -C 10 hydroxyalkyl, C 1 -C 10 thioalkyl and C 1 -C 10 nitroalkyl, OR 2 , SR 2 (CR 3 NR 4 R 5 ), NR 4 R 5 , (C═N—R 4 )R 6 , N═O, N(═O) 2 , NR 4 OR 7 or SO 4 R 7 ;
R 2 is selected from H, C 1 -C 10 alkyl, C 2 -C 10 arylalkyl, C 3 -C 6 cycloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 heteroarylalkyl, C 2 -C 10 haloalkyl, C 2 -C 10 dihaloalkyl, C 2 -C 10 trihaloalkyl, (CR 3 NR 4 R 5 ), NR 4 R 5 , (C═N—R 4 )R 6 , N═O, N(═O) 2 or NR 4 OR 7 ;
R 3 is selected from H, C 1 -C 10 alkyl, C 2 -C 10 arylalkyl, C 3 -C 6 cycloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 heteroarylalkyl, C 2 -C 10 haloalkyl, C 2 -C 10 dihaloalkyl, C 2 -C 10 trihaloalkyl, C 2 -C 10 haloalkoxy, OR 7 , SR 7 , (CR 8 NR 4 R 5 ), NR 4 R 5 , (C═N—R 1 )R 6 , N═O, N(═O) 2 , NR 4 OR 7 or SO 4 R 7 ;
R 4 and R 5 are independently selected from H, C 1 -C 10 alkyl, C 2 -C 10 arylalkyl, C 3 -C 6 cycloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 heteroarylalkyl, C 2 -C 10 haloalkyl, C 2 -C 10 dihaloalkyl, C 2 -C 10 trihaloalkyl, OR 7 or SR 7 .
27 . The method of claim 26 , wherein the compound is selected from flavesone (1-isobutyroyl-3,3,5,5-tetramethylcyclohexan-2,4,6-trione), isoleptospermone (1-isovaleroyl-3,3,5,5-tetramethylcyclohexan-2,4,6-trione), leptospermone (1-valeroyl-3,3,5,5-tetramethylcyclohexan-2,4,6-trione), papuanone (1-pentoyl-3,3,5,5-tetramethylcyclohexan-2,4,6-trione), grandiflorone (1-(2-phenylethyl)-3,3,5,5-tetramethylcyclohexan-2,4,6-trione) and jensenone (1-valeroyl-3,5-dicarbonylcyclohexan-2,4,6-trione), including analogues and derivatives thereof.
28 . The method of claim 26 , wherein the compound has a structural formula selected from:
29 . The method of claim 26 , wherein the compound has a structural formula selected from:
30 . The method of claim 26 , wherein the compound has a structural formula selected from:
31 . The method of claim 26 , wherein the compound has a structural formula selected from:
32 . The method of claim 25 , wherein the compound is represented by the general formula (IV)
wherein
X and Y are each independently selected from oxygen, sulfur —N—R 4 or one of C═X or C═Y is CH 2 ;
A is (C═O)R 1 , (C═S)R 1 , OR 2 , SR 2 , (CR 3 NR 4 R), C(R 3 ) 2 OR 2 , NR 4 R 5 , (C═N—R 4 )R 1 , N═O, N(═O) 2 , NR 4 OR 2 or SO 4 R 2 ;
B is H, C 1 -C 10 alkyl, C 2 -C 10 alkenyl, aryl or heteroaryl;
C, D, E and F are each independently selected from H, C 1 -C 10 alkyl, C 2 -C 10 arylalkyl, C 3 -C 6 cycloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 heteroarylalkyl, C 2 -C 10 haloalkyl, C 2 -C 10 dihaloalkyl, C 2 -C 10 trihaloalkyl, C 2 -C 10 haloalkoxy, OR 2 , SR 2 , (CR 3 NR 4 R 5 ), NR 4 R 5 , (C═N—R 4 )R 1 , N═O, N(═O) 2 , NR 4 OR 2 , SO 4 R 2 ; and
R 1 is selected from H, C 1 -C 10 alkyl, C 2 -C 10 arylalkyl, C 3 -C 6 cycloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 heteroarylalkyl, C 1 -C 10 haloalkyl, C 1 -C 10 dihaloalkyl, C 2 -C 10 trihaloalkyl, C 2 -C 10 haloalkoxy, C 1 -C 10 hydroxyalkyl, C 1 -C 10 thioalkyl and C 1 -C 10 nitroalkyl, OR 2 , SR 2 , (CR 3 NR 4 R 5 ), NR 4 R 5 , (C═N—R 4 )R 6 , N═O, N(═O) 2 , NR 4 OR 7 or SO 4 R 7 ;
R 2 is selected from H, C 1 -C 10 alkyl, C 2 -C 10 cloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 heteroarylalkyl, C 1 -C 10 haloalkyl, C 1 -C 10 dihaloalkyl, C 2 -C 10 trihaloalkyl, (CR 3 NR 4 R 5 ), NR 4 R 5 , (C═N—R 4 )R 6 , N═O, N(═O) 2 or NR 4 OR 7 ;
R 3 is selected from H, C 1 -C 10 alkyl, C 2 -C 10 arylalkyl, C 3 -C 6 cycloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 , heteroarylalkyl, C 2 -C 10 haloalkyl, C 2 -C 10 dihaloalkyl, C 2 -C 10 trihaloalkyl, C 2 -C 10 haloalkoxy, OR 7 , SR 7 , (CR 8 NR 4 R 5 ), NR 4 R 5 , (C═N—R 4 )R 6 , N═O, N(═O) 2 , NR 4 OR 7 or SO 4 R 7 ;
R 1 and R 5 are independently selected from H, C 1 -C 10 alkyl, C 2 -C 10 arylalkyl, C 3 -C 6 cycloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 heteroarylalkyl, C 2 -C 10 haloalkyl, C 2 -C 10 dihaloalkyl, C 2 -C 10 trihaloalkyl, OR 7 or SR 7 .
33 . The method of claim 32 , wherein the compound is selected from tasmanone (1-isobutroyl-4-methoxy-3,5,5-trimethylcyclohex-3-en-2,6-dione), agglomerone (1-isobutroyl-4-methoxy-5,5-dimethylcyclohex-3-en-2,6-dione), lateriticone (1-valeroyl-4-methoxy-3,5,5-trimethylcyclohex-3-en-2,6-dione), isolateriticone (1-isovaleroyl-4-methoxy-3,5,5-trimethylcyclohex-3-en-2,6-dione and platyphyllol (6,6-dimethyl-2-acetyl-5-methoxycyclohex-4-ene-1,3-dione), including analogues and derivatives thereof.
34 . The method of claim 32 , wherein the compound has a structural formula selected from:
35 . The method of claim 25 , wherein the compound is represented by the general formula (V)
wherein
X and Y are independently selected from oxygen, sulfur or —N—R 4 ; and
A is (C═O)R 1 , (C═S)R 1 , OR 2 , SR 2 , (CR 3 NR 4 R 5 ), C(R 3 ) 2 OR 2 , NR 4 R 5 , (C═N—R 4 )R 1 , N═O, N(═O) 2 , NR 4 OR 2 or SO 4 R 2 ;
B is H, C 1 -C 10 alkyl C 2 -C 10 alkenyl, aryl or heteroaryl;
C, D, E, F, G and H are each independently selected from H, C 1 -C 10 alkyl, C 2 -C 10 arylalkyl, C 3 -C 6 cycloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 heteroarylalkyl, C 2 -C 10 haloalkyl, C 2 -C 10 dihaloalkyl, C 2 -C 10 trihaloalkyl, C 2 -C 10 haloalkoxy, OR 2 , SR 2 , (CR 3 NR 4 R 5 ), NR 4 R 5 , (C═N—R 4 )R 1 , N═O, N(═O) 2 , NR 4 OR 2 or SO 4 R 2 ; and
R 1 is selected from H, C 1 -C 10 alkyl, C 2 -C 10 arylalkyl, C 3 -C 6 cycloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 heteroarylalkyl, C 1 -C 10 haloalkyl, C 1 -C 10 dihaloalkyl, C 2 -C 10 trihaloalkyl, C 2 -C 10 haloalkoxy, C 1 -C 10 hydroxyalkyl, C 1 -C 10 thioalkyl and C 1 -C 10 nitroalkyl, OR 2 , SR 2 , (CR 3 NR 4 R 5 ), NR 4 R 5 , (C═N—R 4 )R 6 , N═O, N(═O) 2 , NR 4 OR 7 or SO 4 R 7 ;
R 2 is selected from H, C 1 -C 10 alkyl, C 2 -C 10 arylalkyl, C 3 -C 6 cycloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 heteroarylalkyl, C 2 -C 10 haloalkyl, C 2 -C 10 dihaloalkyl, C 2 -C 10 trihaloalkyl, (CR 3 NR 4 R 5 ), NR 4 R 5 , (C═N—R 4 )R 6 , N═O, N(═O) 2 or NR 4 OR 7 ;
R 3 is selected from H, C 1 -C 10 alkyl C 2 -C 10 arylalkyl, C 3 -C 6 cycloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 heteroarylalkyl, C 2 -C 10 haloalkyl, C 2 -C 10 dihaloalkyl, C 2 -C 10 trihaloalkyl, C 2 -C 10 haloalkoxy, OR 7 , SR 7 , (CR 8 NR 4 R 5 ), NR 4 R 5 , (C═N—R 4 )R 6 , N═O, N(═O) 2 , NR 4 OR 7 or SO 4 R 7 ;
R 4 and R 5 are independently selected from H, C 1 -C 10 alkyl, C 2 -C 10 arylalkyl, C 3 -C 6 cycloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 heteroarylalkyl, C 2 -C 10 haloalkyl, C 2 -C 10 dihaloalkyl, C 2 -C 10 trihaloalkyl, OR 7 or SR 7 .
36 . The method of claim 35 , wherein the compound is selected from are angustione (1-acetyl-3,5,5-trimethylcyclohex-2,6-dione), dehydroangustione (1-acetyl-3,5,5-trimethylcyclohex-3-en-2,6-dione) and xanthostemone (1-isobutroyl-5,5-dimethylcyclohex-3-en-2,6-dione), including their analogues and derivatives.
37 . The method of claim 35 , wherein the compound has a structural formula selected from:
38 . The method of claim 35 , wherein the compound has a structural formula selected from:
39 . The method of claim 35 , wherein the compound has a structural formula selected from:
40 . The method of claim 25 , wherein the compound is obtainable from a volatile oil-bearing organism.
41 . The method of claim 40 , wherein the compound is present in an essential oil derived from said volatile oil-bearing organism.
42 . The method of claim 40 , wherein the volatile oil-bearing organism is selected from volatile oil-bearing plants.
43 . The method of claim 40 , wherein the volatile oil-bearing organism is selected from plants from the families Alliaceae, Apiaceae, Asteraceae, Cannabinaceae, Lamiaceae, Pteridaceae, Myrtaceae, Myoporaceae, Proteaceae, Rutaceae and Zingiberaceae.
44 . The method of claim 40 , wherein the volatile oil-bearing organism is selected from genera of the Myrtaceae family.
45 . The method of claim 40 , wherein the volatile oil-bearing organism belongs to a genus selected from Angophora, Austromyrtus, Backhousia, Baeckea, Callistemon, Corymbia, Darwinia, Eucalyptus, Kunzea, Leptospermum, Melaleuca, Syzygium and Xanthostemon
46 . The method of claim 25 , wherein the pest that is controlled is selected from insects, arachnids, helminths, molluscs, protozoa and viruses.
47 . The method of claim 25 , wherein the pest that is controlled is selected from insects, arachnids, helminths and molluscs.
48 . The method of claim 25 , wherein the compound is used in the form of, a pest-controlling composition which comprises from about 0.00005% to about 90% by weight of said compound.
49 .- 73 . (canceled)
74 . A method for controlling harmful, annoying or undesired pests, other than plants and microbes, said method comprising exposing said pests to a pest-controlling effective amount of a composition comprising a β-dione compound represented by the general formula (I)
wherein
A is (C═O)R 1 , (C═S)R 1 , OR 2 , SR 2 , (CR 3 NR 4 R 5 ), C(R 3 ) 2 OR 2 , NR 4 R 5 , (C═N—R 4 )R 1 , N═O, N(═O) 2 , NR 4 OR 2 or SO 4 R 2 ;
R 1 is selected from H, C 1 -C 10 alkyl, C 2 -C 10 arylalkyl, C 3 -C 6 cycloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 heteroarylalkyl, C 1 -C 10 haloalkyl, C 1 -C 10 dihaloalkyl, C 2 -C 10 trihaloalkyl, C 2 -C 10 haloalkoxy, C 1 -C 10 hydroxyalkyl, C 1 -C 10 thioalkyl and C 1 -C 10 nitroalkyl, OR 2 , SR 2 , (CR 3 NR 4 R 5 ), NR 4 R 5 , (C═N—R 4 )R, N═O, N(═O) 2 , NR 4 OR 7 or SO 4 R 7 ;
R 2 is selected from H, C 1 -C 10 alkyl, C 2 -C 10 arylalkyl, C 3 -C 6 cycloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 heteroarylalkyl, C 2 -C 10 haloalkyl, C 2 -C 10 dihaloalkyl, C 2 -C 10 trihaloalkyl, (CR 3 NR 4 R 5 ), NR 4 R 5 , (C═N—R 4 )R 6 , N═O, N(═O) 2 or NR 4 OR 7 ;
R 3 is selected from H, C 1 -C 10 alkyl, C 2 -C 10 arylalkyl, C 3 -C 6 cycloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 heteroarylalkyl, C 2 -C 10 haloalkyl, C 2 -C 10 dihaloalkyl, C 2 -C 10 trihaloalkyl, C 2 -C 10 haloalkoxy, OR 7 , SR 7 , (CR 8 NR 4 R 5 ), NR 4 R 5 , (C═N—R 4 )R 6 , N═O, N(═O) 2 , NR 4 OR 7 or SO 4 R 7 ;
R 4 and R 5 are independently selected from H, C 1 -C 10 alkyl, C 2 -C 10 arylalkyl, C 3 -C 6 cycloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 heteroarylalkyl, C 2 -C 10 haloalkyl, C 2 -C 10 dihaloalkyl, C 2 -C 10 trihaloalkyl, OR 7 or SR 7 ;
R 6 is selected from H, C 1 -C 10 alkyl, C 2 -C 10 arylalkyl, C 3 -C 6 cycloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 heteroarylalkyl, C 2 -C 10 haloalkyl, C 2 -C 10 dihaloalkyl, C 2 -C 10 trihaloalkyl, C 2 -C 10 haloalkoxy, OR 7 , SR 7 , (CR 8 NR 9 R 10 ), NR 9 R 10 or NR 9 OR 7 ;
R 7 is selected from H, C 1 C 10 alkyl, C 2 -C 10 arylalkyl, C 3 -C 6 cycloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 heteroarylalkyl, C 2 -C 10 haloalkyl, C 2 -C 10 dihaloalkyl, C 2 -C 10 trihaloalkyl;
R 8 is selected from H, C 1 -C 10 alkyl, C 2 -C 10 arylalkyl, C 3 -C 6 cycloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 heteroarylalkyl, C 2 -C 10 haloalkyl, C 2 -C 10 dihaloalkyl, C 2 -C 10 trihaloalkyl, OR 11 , SR 11 or NR 9 R 10 ;
R 9 and R 10 are independently selected from H, C 1 -C 10 alkyl, C 2 -C 10 arylalkyl, C 3 -C 6 cycloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 heteroarylalkyl, C 2 -C 10 haloalkyl, C 2 -C 10 dihaloalkyl, C 2 -C 10 trihaloalkyl, OR 12 or SR 12 ;
R 11 is selected from H, C 1 -C 10 alkyl, C 2 -C 10 arylalkyl, C 3 -C 6 cycloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 heteroarylalkyl, C 2 -C 10 haloalkyl, C 2 -C 10 dihaloalkyl, C 2 -C 10 trihaloalkyl;
R 12 is selected from H, C 1 -C 10 alkyl, C 2 -C 10 arylalkyl, C 3 -C 6 cycloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 heteroarylalkyl, C 2 -C 10 haloalkyl, C 2 -C 10 dihaloalkyl, C 2 -C 10 trihaloalkyl;
B is H, C 1 -C 10 alkyl, C 2 -C 10 alkenyl, aryl or heteroaryl;
X and Y are independently selected from oxygen, sulfur, —N—R 4 ; and
Q completes a 5-8-member saturated or unsaturated carbocyclic or heterocyclic ring,
with the proviso that when B═H 1 , C 1 -C 10 , alkyl or aryl, A is not CR 3 NR 4 R 5 or C(R 3 ) 2 OR 2 .
75 . The method of claim 74 , wherein the compound is represented by the general formula (III)
wherein
X, Y and Z are each independently selected from oxygen, sulfur, —N—R 4 or one of C═X, C═Y or C=Z is CH 2 ;
A is (C═O)R 1 , (C═S)R 1 , OR 2 , SR 2 , (CR 3 NR 4 R 5 ), C(R 3 ) 2 OR 2 , NR 4 R 5 , (C═N—R 4 )R 1 , N═O, N(═O) 2 , NR 4 OR 2 or SO 4 R 2 ;
B is H, C 1 -C 10 alkyl, C 2 -C 10 alkenyl, aryl or heteroaryl;
C, D, E and F are each independently selected from H, C 1 -C 10 alkyl, C 3 -C 6 cycloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 haloalkyl, C 2 -C 10 dihaloalkyl, C 2 -C 10 trihaloalkyl, OR 2 , SR 2 , (CR 3 NR 4 R 5 ), NR 4 R 5 , (C═N—R 4 )R 1 , N═O, N(═O) 2 , NR 4 OR 2 , SO 4 R 2 , C 2 -C 10 1-arylalkyl, C 2 -C 10 2-arylalkyl or (C═X)R 1 ; and
R 1 is selected from H, C 1 -C 10 alkyl, C 2 -C 10 arylalkyl, C 3 -C 6 cycloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 heteroarylalkyl, C 1 -C 10 haloalkyl, C 1 -C 10 dihaloalkyl, C 2 -C 10 trihaloalkyl, C 2 -C 10 haloalkoxy, C 1 -C 10 hydroxyalkyl, C 1 -C 10 thioalkyl and C 1 -C 10 nitroalkyl, OR 2 , SR 2 , (CR 3 NR 4 R 5 ), NR 4 R 5 , (C═N—R 4 )R 6 , N═O, N(═O) 2 , NR 4 OR 7 or SO 4 R 7 ;
R 2 is selected from H, C 1 -C 10 alkyl, C 2 -C 10 arylalkyl, C 3 -C 6 cycloalky, C 2 -C 10 alkenyl, C 2 -C 10 heteroarylalkyl, C 2 -C 10 haloalkyl, C 2 -C 10 dihaloalkyl, C 2 -C 10 trihaloalkyl, (CR 3 NR 4 R 5 ), NR 4 R 5 , (C═N—R 1 )R 6 , N═O, N(═O) 2 or NR 4 OR 7 ;
R 3 is selected from H, C 1 -C 10 alkyl, C 2 -C 10 arylalkyl, C 3 -C 6 cycloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 heteroarylalkyl, C 2 -C 10 haloalkyl, C 2 -C 10 dihaloalkyl, C 2 -C 10 trihaloalkyl, C 2 -C 10 haloalkoxy, OR 7 , SR 7 , (CR 8 NR 4 R 5 ), NR 4 R 5 , (C═N—R 4 )R 6 , N═O, N(═O) 2 , NR 4 OR 7 or SO 4 R 7 ;
R 4 and R 5 are independently selected from H, C 1 -C 10 alkyl, C 2 -C 10 arylalkyl, C 3 -C 6 cycloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 heteroarylalkyl, C 2 -C 10 haloalkyl, C 2 -C 10 dihaloalkyl, C 2 -C 10 trihaloalkyl, OR 7 or SR 7 ,
with the proviso that when B═H 1 , C 1 -C 10 , alkyl or aryl, A is not CR 3 NR 4 R 5 or C(R 3 ) 2 OR 2 .
76 . The method of claim 75 , wherein the compound is selected from flavesone (1-isobutyroyl-3,3,5,5-tetramethylcyclohexan-2,4,6-trione), isoleptospermone (1-isovaleroyl-3,3,5,5-tetramethylcyclohexan-2,4,6-trione), leptospermone (1-valeroyl-3,3,5,5-tetramethylcyclohexan-2,4,6-trione), papuanone (1-pentoyl-3,3,5,5-tetramethylcyclohexan-2,4,6-trione), grandiflorone (1-(2-phenylethyl)-3,3,5,5-tetramethylcyclohexan-2,4,6-trione) and jensenone (1-valeroyl-3,5-dicarbonylcyclohexan-2,4,6-trione), including analogues and derivatives thereof.
77 . The method of claim 75 , wherein the compound has a structural formula selected from:
78 . The method of claim 75 , wherein the compound has a structural formula selected from:
79 . The method of claim 75 , wherein the compound has a structural formula selected from:
80 . The method of claim 75 , wherein the compound has a structural formula selected from:
81 . The method of claim 74 , wherein the compound is represented by the general formula (IV)
wherein
X and Y are each independently selected from oxygen, sulfur —N—R 4 or one of C═X or C═Y is CH 2 ;
A is (C═O)R 1 , (C═S)R 1 , OR 2 , SR 2 , (CR 3 NR 4 R 5 ), C(R 3 ) 2 OR 2 , NR 4 R 5 , (C═N—R 4 )R 1 , N═O, N(═O) 2 , NR 4 OR 2 or SO 4 R 2 ;
B is H, C 1 -C 10 alkyl, C 2 -C 10 alkenyl, aryl or heteroaryl;
C, D, E and F are each independently selected from H, C 1 -C 10 alkyl, C 2 -C 10 arylalkyl, C 3 -C 6 cycloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 heteroarylalkyl, C 2 -C 10 haloalkyl, C 2 -C 10 dihaloalkyl, C 2 -C 10 trihaloalkyl, C 2 -C 10 haloalkoxy, OR 2 , SR 2 , (CR 3 NR 4 R 5 ), NR 4 R 5 , (C═N—R 4 )R 1 , N═O, N(═O) 2 , NR 4 OR 2 , SO 4 R 2 ; and
R 1 is selected from H, C 1 -C 10 alkyl C 2 -C 10 arylalkyl, C 3 -C 6 cycloalkyl, C 2 -C 10 alkenyl. C 2 -C 10 heteroarylalkyl, C 1 -C 10 haloalkyl, C 1 -C 10 dihaloalkyl, C 2 -C 10 trihaloalkyl, C 2 -C 10 haloalkoxy. C 1 -C 10 hydroxyalkyl, C 1 -C 10 thioalkyl and C 1 -C 10 nitroalkyl, OR 2 , SR 2 , (CR 3 NR 4 R 5 ), NR 4 R 5 , (C═N—R 4 )R 6 , N═O, N(═O) 2 , NR 4 OR 7 or SO 4 R 7 ;
R 2 is selected from H, C 1 -C 10 alkyl, C 2 -C 10 arylalkyl, C 3 -C 6 cycloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 heteroarylalkyl, C 2 -C 10 haloalkyl, C 2 -C 10 dihaloalkyl, C 2 -C 10 trihaloalkyl, (CR 3 NR 4 R 5 ), NR 4 R 5 , (C═N—R 4 )R 6 , N═O, N(═O 2 ) or NR 4 OR 7 ;
R 3 is selected from H, C 1 -C 10 alkyl, C 2 -C 10 arylalkyl C 3 -C 6 cycloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 heteroarylalkyl, C 2 -C 10 haloalkyl, C 2 -C 10 dihaloalkyl, C 2 -C 10 trihaloalkyl, C 2 -C 10 haloalkoxy, OR 7 , SR 7 , (CR 8 NR 4 R 5 ), NR 4 R 5 , (C═N—R 4 )R 6 , N═O, N(═O) 2 , NR 4 OR 7 or SO 4 R 7 ;
R 4 and R 5 are independently selected from H, C 1 -C 10 alkyl C 2 -C 10 arylalkyl, C 3 -C 6 cycloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 heteroarylalkyl, C 2 -C 10 haloalkyl, C 2 -C 10 dihaloalkyl, C 2 -C 10 trihaloalkyl, OR 7 or SR 7 ,
with the proviso that when B═H 1 , C 1 -C 10 , alkyl or aryl, A is not CR 3 NR 4 R 5 or C(R 3 ) 2 OR 2 .
82 . The method of claim 81 , wherein the compound is selected from tasmanone (1-isobutroyl-4-methoxy-3,5,5-trimethylcyclohex-3-en-2,6-dione), agglomerone (1-isobutroyl-4-methoxy-5,5-dimethylcyclohex-3-en-2,6-dione), lateriticone (1-valeroyl-4-methoxy-3,5,5-trimethylcyclohex-3-en-2,6-dione), isolateriticone (1-isovaleroyl-4-methoxy-3,5,5-trimethylcyclohex-3-en-2,6-dione and platyphyllol (6,6-dimethyl-2-acetyl-5-methoxycyclohex-4-ene-1,3-dione), including analogues and derivatives thereof.
83 . The method of claim 81 , wherein the compound has a structural formula selected from:
84 . The method of claim 74 , wherein the compound is represented by the general formula (V)
wherein
X and Y are independently selected from oxygen, sulfur or —N—R 4 ; and
A is (C═O)R 1 , (C═S)R 1 , OR 2 , SR 2 , (CR 3 NR 4 R 5 ), C(R 3 ) 2 OR 2 , NR 4 R 5 , (C═N—R 4 )R 1 , N═O, N(═O) 2 , NR 4 OR 2 or SO 4 R 2 ;
B is H, C 1 -C 10 alkyl, C 2 -C 10 alkenyl, aryl or heteroaryl;
C, D, E, F, G and H are each independently selected from H, C 1 -C 10 alkyl, C 2 -C 10 arylalkyl, C 3 -C 6 cycloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 heteroarylalkyl, C 2 -C 10 haloalkyl, C 2 -C 10 dihaloalkyl, C 2 -C 10 trihaloalkyl, C 2 -C 10 haloalkoxy, OR 2 , SR 2 , (CR 3 NR 4 R 5 ), NR 4 R 5 , (C═N—R 4 )R 1 , N═O, N(═O) 2 , NR 4 OR 2 or SO 4 R 2 ; and
R 1 is selected from H, C 1 -C 10 alkyl, C 2 -C 10 arylalkyl, C 3 -C 6 cycloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 heteroarylalkyl, C 1 -C 10 haloalkyl, C 1 -C 10 dihaloalkyl, C 2 -C 10 trihaloalkyl, C 2 -C 10 haloalkoxy, C 1 -C 10 hydroxyalkyl, C 1 -C 10 thioalkyl and C 1 -C 10 nitroalkyl, OR 2 , SR 2 , (CR 3 NR 4 R 5 ), NR 4 R 5 , (C═N—R 4 )R 6 , N═O, N(═O) 2 or NR 4 OR 7 or SO 4 R 7 ;
R 2 is selected from H, C 1 -C 10 alkyl, C 2 -C 10 arylalkyl, C 3 -C 6 cycloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 heteroarylalkyl, c 2 -C 10 haloalkyl, C 2 -C 10 dihaloalkyl, C 2 -C 10 trihaloalkyl, (CR 3 NR 4 R 5 ), NR 4 R 5 , (C═N—R 4 )R 6 , N═O, N(═O) 2 or NR 4 OR 7 ;
R 3 is selected from H, C 1 -C 10 alkyl, C 2 -C 10 arylalkyl, c 3 -C 6 cycloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 heteroarylalkyl, C 2 -C 10 haloalkyl, C 2 -C 10 dihaloalkyl, C 2 -C 10 trihaloalkyl, C 2 -C 10 haloalkoxy, OR 7 , SR 7 , (CR 8 NR 4 R 5 ), NR 4 R 5 , (C═N—R 4 )R 6 , N═O, N(═O) 2 , NR 4 OR 7 or SO 4 R 7 ;
R 4 and R 5 are independently selected from H, C 1 -C 10 alkyl, C 2 -C 10 arylalkyl, C 3 -C 6 cycloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 heteroarylalkyl, C 2 -C 10 haloalkyl, C 2 -C 10 dihaloalkyl, C 2 -C 10 trihaloalkyl, OR 7 or SR 7 ,
with the proviso that when B═H 1 , C 1 -C 10 , alkyl or aryl, A is not CR 3 NR 4 R 5 or C(R 3 ) 2 OR 2 .
85 . The method of claim 84 , wherein the compound is selected from are angustione (1-acetyl-3,5,5-trimethylcyclohex-2,6-dione), dehydroangustione (1-acetyl-3,5,5-trimethylcyclohex-3-en-2,6-dione) and xanthostemone (1-isobutroyl-5,5-dimethylcyclohex-3-en-2,6-dione), including their analogues and derivatives.
86 . The method of claim 35 , wherein the compound has a structural formula selected from:
87 . The method of claim 84 , wherein the compound has a structural formula selected from:
88 . The method of claim 84 , wherein the compound has a structural formula selected from:
89 . The method of claim 74 , wherein the compound is obtainable from a volatile oil-bearing organism.
90 . The method of claim 89 , wherein the compound is present in an essential oil derived from said volatile oil-bearing organism.
91 . The method of claim 89 , wherein the volatile oil-bearing organism is selected from volatile oil-bearing plants.
92 . The method of claim 89 , wherein the volatile oil-bearing organism is selected from plants from the families Alliaceae, Apiaceae, Asteraceae, Cannabinaceae, Lamiaceae, Pteridaceae, Myrtaceae, Myoporaceae, Proteaceae, Rutaceae and Zingiberaceae.
93 . The method of claim 89 , wherein the volatile oil-bearing organism is selected from genera of the Myrtaceae family.
94 . The method of claim 89 , wherein the volatile oil-bearing organism belongs to a genus selected from Angophora, Austromyrtus, Backhousia, Baeckea, Callistemon, Corymbia, Darwinia, Eucalyptus, Kunzea, Leptospermum, Melaleuca, Syzygium and Xanthostemon
95 . The method of claim 74 , wherein the pest that is controlled is selected from insects, arachnids, helminths, molluscs, protozoa and viruses.
96 . The method of claim 74 , wherein the pest that is controlled is selected from insects, arachnids, helminths and molluscs.
97 . The method of claim 74 , wherein the compound is used in the form of a pest-controlling composition which comprises from about 0.00005% to about 90% by weight of said compound.
98 . The method of claim 25 , wherein Q completes the 5-8-member saturated or unsaturated carbocyclic or heterocyclic ring in which one or more members comprise —C(═X)—; and wherein Q is substituted with one or more substituents selected from C 1 -C 10 alkyl, C 3 -C 6 cycloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 haloalkyl, C 2 -C 10 dihaloalkyl, C 2 -C 10 trihaloalkyl, C 2 -C 10 haloalkoxy, OR 2 , SR 2 , (CR 3 NR 4 R 5 ), NR 4 R 5 , (C═N—R 4 )R 1 , N═O, N(═O) 2 , NR 4 OR 2 , SO 4 R 2 , C 2 -C 10 1-arylalkyl, C 2 -C 10 2-arylalkyl or (C═X)R 1 .
99 . The method of claim 74 , wherein Q completes the 5-8-member saturated or unsaturated carbocyclic or heterocyclic ring in which one or more members comprise —C(═X)—; and wherein Q is substituted with one or more substituents selected from C 1 -C 10 alkyl, C 3 -C 6 cycloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 haloalkyl, C 2 -C 10 dihaloalkyl, C 2 -C 10 trihaloalkyl, C 2 -C 10 haloalkoxy, OR 2 , SR 2 , (CR 3 NR 4 R 5 ), NR 4 R 5 , (C═N—R 4 )R 1 , N═O, N(═O) 2 , NR 4 OR 2 , SO 4 R 2 , C 2 -C 10 1-arylalkyl, C 2 -C 10 2-arylalkyl or (C═X)R 1 .Join the waitlist — get patent alerts
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