CA2545076A1 - Insect behaviour modifying compounds - Google Patents
Insect behaviour modifying compounds Download PDFInfo
- Publication number
- CA2545076A1 CA2545076A1 CA002545076A CA2545076A CA2545076A1 CA 2545076 A1 CA2545076 A1 CA 2545076A1 CA 002545076 A CA002545076 A CA 002545076A CA 2545076 A CA2545076 A CA 2545076A CA 2545076 A1 CA2545076 A1 CA 2545076A1
- Authority
- CA
- Canada
- Prior art keywords
- thrips
- isonicotinate
- formula
- compound
- ethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 150000001875 compounds Chemical class 0.000 title claims 20
- 241000238631 Hexapoda Species 0.000 title 1
- 241001414989 Thysanoptera Species 0.000 claims abstract 25
- 125000000217 alkyl group Chemical group 0.000 claims 10
- 241000196324 Embryophyta Species 0.000 claims 8
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 239000001257 hydrogen Substances 0.000 claims 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 6
- BGUWFUQJCDRPTL-UHFFFAOYSA-N pyridine-4-carbaldehyde Chemical compound O=CC1=CC=NC=C1 BGUWFUQJCDRPTL-UHFFFAOYSA-N 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 230000001276 controlling effect Effects 0.000 claims 4
- 230000001105 regulatory effect Effects 0.000 claims 4
- FHHKAXDNIISDHM-UHFFFAOYSA-N 1-pyridin-4-ylbutan-1-one Chemical compound CCCC(=O)C1=CC=NC=C1 FHHKAXDNIISDHM-UHFFFAOYSA-N 0.000 claims 3
- WMQUKDQWMMOHSA-UHFFFAOYSA-N 1-pyridin-4-ylethanone Chemical compound CC(=O)C1=CC=NC=C1 WMQUKDQWMMOHSA-UHFFFAOYSA-N 0.000 claims 3
- AFHFHXVRHACYSR-UHFFFAOYSA-N 1-pyridin-4-ylpropan-1-one Chemical compound CCC(=O)C1=CC=NC=C1 AFHFHXVRHACYSR-UHFFFAOYSA-N 0.000 claims 3
- FCQDHSSRNVWWOE-UHFFFAOYSA-N decyl pyridine-4-carboxylate Chemical compound CCCCCCCCCCOC(=O)C1=CC=NC=C1 FCQDHSSRNVWWOE-UHFFFAOYSA-N 0.000 claims 3
- IGRLNCOFYMWKBU-UHFFFAOYSA-N ethyl 2-chloropyridine-4-carboxylate Chemical compound CCOC(=O)C1=CC=NC(Cl)=C1 IGRLNCOFYMWKBU-UHFFFAOYSA-N 0.000 claims 3
- MCRPKBUFXAKDKI-UHFFFAOYSA-N ethyl pyridine-4-carboxylate Chemical compound CCOC(=O)C1=CC=NC=C1 MCRPKBUFXAKDKI-UHFFFAOYSA-N 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- OLXYLDUSSBULGU-UHFFFAOYSA-N methyl pyridine-4-carboxylate Chemical compound COC(=O)C1=CC=NC=C1 OLXYLDUSSBULGU-UHFFFAOYSA-N 0.000 claims 3
- HLRSGDOBQLTYNO-UHFFFAOYSA-N n,n-di(propan-2-yl)pyridine-4-carboxamide Chemical compound CC(C)N(C(C)C)C(=O)C1=CC=NC=C1 HLRSGDOBQLTYNO-UHFFFAOYSA-N 0.000 claims 3
- KGVUTEGTZWOIIN-UHFFFAOYSA-N o-pyridin-4-yl ethanethioate Chemical compound CC(=S)OC1=CC=NC=C1 KGVUTEGTZWOIIN-UHFFFAOYSA-N 0.000 claims 3
- FBDVYRNKUYCAGB-UHFFFAOYSA-N propan-2-yl pyridine-4-carboxylate Chemical compound CC(C)OC(=O)C1=CC=NC=C1 FBDVYRNKUYCAGB-UHFFFAOYSA-N 0.000 claims 3
- TZAAGDYITBGHOB-UHFFFAOYSA-N propyl pyridine-4-carboxylate Chemical compound CCCOC(=O)C1=CC=NC=C1 TZAAGDYITBGHOB-UHFFFAOYSA-N 0.000 claims 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 3
- GPHQHTOMRSGBNZ-UHFFFAOYSA-N pyridine-4-carbonitrile Chemical compound N#CC1=CC=NC=C1 GPHQHTOMRSGBNZ-UHFFFAOYSA-N 0.000 claims 3
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 claims 2
- 244000291564 Allium cepa Species 0.000 claims 2
- 235000002732 Allium cepa var. cepa Nutrition 0.000 claims 2
- 240000007124 Brassica oleracea Species 0.000 claims 2
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 claims 2
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 claims 2
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 claims 2
- NUPSHWCALHZGOV-UHFFFAOYSA-N Decyl acetate Chemical compound CCCCCCCCCCOC(C)=O NUPSHWCALHZGOV-UHFFFAOYSA-N 0.000 claims 2
- VZWGRQBCURJOMT-UHFFFAOYSA-N Dodecyl acetate Chemical compound CCCCCCCCCCCCOC(C)=O VZWGRQBCURJOMT-UHFFFAOYSA-N 0.000 claims 2
- ZFMSMUAANRJZFM-UHFFFAOYSA-N Estragole Chemical compound COC1=CC=C(CC=C)C=C1 ZFMSMUAANRJZFM-UHFFFAOYSA-N 0.000 claims 2
- XBLVHTDFJBKJLG-UHFFFAOYSA-N Ethyl nicotinate Chemical compound CCOC(=O)C1=CC=CN=C1 XBLVHTDFJBKJLG-UHFFFAOYSA-N 0.000 claims 2
- WEEGYLXZBRQIMU-UHFFFAOYSA-N Eucalyptol Chemical compound C1CC2CCC1(C)OC2(C)C WEEGYLXZBRQIMU-UHFFFAOYSA-N 0.000 claims 2
- 206010061217 Infestation Diseases 0.000 claims 2
- 241000208822 Lactuca Species 0.000 claims 2
- 235000003228 Lactuca sativa Nutrition 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 239000005667 attractant Substances 0.000 claims 2
- 230000031902 chemoattractant activity Effects 0.000 claims 2
- 235000013399 edible fruits Nutrition 0.000 claims 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 claims 2
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- -1 isopentenyl Chemical group 0.000 claims 2
- VAMXMNNIEUEQDV-UHFFFAOYSA-N methyl anthranilate Chemical compound COC(=O)C1=CC=CC=C1N VAMXMNNIEUEQDV-UHFFFAOYSA-N 0.000 claims 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims 2
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 claims 2
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 claims 2
- 235000013311 vegetables Nutrition 0.000 claims 2
- PSQYTAPXSHCGMF-BQYQJAHWSA-N β-ionone Chemical compound CC(=O)\C=C\C1=C(C)CCCC1(C)C PSQYTAPXSHCGMF-BQYQJAHWSA-N 0.000 claims 2
- SFEOKXHPFMOVRM-UHFFFAOYSA-N (+)-(S)-gamma-ionone Natural products CC(=O)C=CC1C(=C)CCCC1(C)C SFEOKXHPFMOVRM-UHFFFAOYSA-N 0.000 claims 1
- KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 claims 1
- KKVZAVRSVHUSPL-GQCTYLIASA-N Cassiastearoptene Chemical compound COC1=CC=CC=C1\C=C\C=O KKVZAVRSVHUSPL-GQCTYLIASA-N 0.000 claims 1
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 claims 1
- 239000005698 Dodecyl acetate Substances 0.000 claims 1
- TWLLPUMZVVGILS-UHFFFAOYSA-N Ethyl 2-aminobenzoate Chemical compound CCOC(=O)C1=CC=CC=C1N TWLLPUMZVVGILS-UHFFFAOYSA-N 0.000 claims 1
- GYCKQBWUSACYIF-UHFFFAOYSA-N Ethyl salicylate Chemical compound CCOC(=O)C1=CC=CC=C1O GYCKQBWUSACYIF-UHFFFAOYSA-N 0.000 claims 1
- 239000005770 Eugenol Substances 0.000 claims 1
- 241000927584 Frankliniella occidentalis Species 0.000 claims 1
- UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 claims 1
- 241001516538 Terebrantia Species 0.000 claims 1
- 241001151781 Thrips obscuratus Species 0.000 claims 1
- 241000339374 Thrips tabaci Species 0.000 claims 1
- ILUAVCBOWYHFAI-SLEUVZQESA-N [(1s,3s,4s)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] pentanoate Chemical compound C1C[C@]2(C)[C@@H](OC(=O)CCCC)C[C@@]1([H])C2(C)C ILUAVCBOWYHFAI-SLEUVZQESA-N 0.000 claims 1
- 229940117916 cinnamic aldehyde Drugs 0.000 claims 1
- KJPRLNWUNMBNBZ-UHFFFAOYSA-N cinnamic aldehyde Natural products O=CC=CC1=CC=CC=C1 KJPRLNWUNMBNBZ-UHFFFAOYSA-N 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 229940005667 ethyl salicylate Drugs 0.000 claims 1
- 229940064982 ethylnicotinate Drugs 0.000 claims 1
- 229960002217 eugenol Drugs 0.000 claims 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 229940102398 methyl anthranilate Drugs 0.000 claims 1
- 229940095102 methyl benzoate Drugs 0.000 claims 1
- 229960001047 methyl salicylate Drugs 0.000 claims 1
- 229930003658 monoterpene Natural products 0.000 claims 1
- 150000002773 monoterpene derivatives Chemical class 0.000 claims 1
- 235000002577 monoterpenes Nutrition 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- GTDQGKWDWVUKTI-UHFFFAOYSA-N o-aminoacetophenone Chemical compound CC(=O)C1=CC=CC=C1N GTDQGKWDWVUKTI-UHFFFAOYSA-N 0.000 claims 1
- KKVZAVRSVHUSPL-UHFFFAOYSA-N o-methoxycinnamic aldehyde Natural products COC1=CC=CC=C1C=CC=O KKVZAVRSVHUSPL-UHFFFAOYSA-N 0.000 claims 1
- 239000003016 pheromone Substances 0.000 claims 1
- 230000001846 repelling effect Effects 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 150000003222 pyridines Chemical class 0.000 abstract 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine Compounds (AREA)
- Catching Or Destruction (AREA)
Abstract
The invention provides methods for controlling thrips populations using thrips-repelling and/or thrips-attracting agents. The agents are derivatives of pyridine. The invention also provides methods of preventing or minimising damage to plants by use of the same.
Claims (43)
1. A method of controlling, surveying or regulating thrips populations by providing at least one thrips behaviour-modifying compound of formula (I) wherein:
R1 is selected from R2, R3, R4 and R5 are each independently selected from hydrogen, halogen, hydroxyl, nitro, or optionally substituted straight or branched chain alkyl, alkenyl, or alkynyl; and R6 is selected from hydrogen or optionally substituted straight or branched chain alkyl, cycloalkyl, alkenyl or alkynyl.
R1 is selected from R2, R3, R4 and R5 are each independently selected from hydrogen, halogen, hydroxyl, nitro, or optionally substituted straight or branched chain alkyl, alkenyl, or alkynyl; and R6 is selected from hydrogen or optionally substituted straight or branched chain alkyl, cycloalkyl, alkenyl or alkynyl.
2. A method according to claim 1 wherein the at least one thrips behaviour-modifying compound of formula (I) is as defined in claim 1 provided that when R' is and R2, R3, R4 and R5 are all hydrogen, R6 is not isopentenyl or hexyl.
3. A method according to claim 1 or claim 2 wherein R2, R3, and R5 are all hydrogen and R4 is halogen.
4. A method according to 1 claim or claim 2 wherein R2, R3, R4 and R5 are all hydrogen.
5. A method according to any one of claims 1 to 4 wherein R1 is , and R6 is as defined in claim 1.
6. A method according to claim 5 wherein R6 is straight or branched chain alkyl.
7. A method according to any one of claims 1 to 4 wherein R1 is , and R6 is as defined in claim 1.
8. A method according to claim 7 wherein R6 is straight or branched chain alkyl.
9. A method according to any one of claims 1 to 4 wherein R1 is , and R6 is as defined in claim 1.
10. A method according to claim 9 wherein R6 is straight or branched chain alkyl.
11. A method according to claim 1 wherein the at least one compound of formula (I) is selected from the group comprising:
methyl isonicotinate;
ethyl isonicotinate;
propyl Isonicotinate;
isopropyl isonicotinate;
decyl isonicotinate;
ethyl 2-chloro-isonicotinate;
pyridine, 4-(1,3-dioxolan-2-yl);
di-isopropyl isonicotinamide;
4-formyl pyridine;
methyl 4-pyridyl ketone;
ethyl 4-pyridyl ketone;
propyl 4-pyridyl ketone;
4-cyanopyridine; and 4-pyridyl thioacetate:
methyl isonicotinate;
ethyl isonicotinate;
propyl Isonicotinate;
isopropyl isonicotinate;
decyl isonicotinate;
ethyl 2-chloro-isonicotinate;
pyridine, 4-(1,3-dioxolan-2-yl);
di-isopropyl isonicotinamide;
4-formyl pyridine;
methyl 4-pyridyl ketone;
ethyl 4-pyridyl ketone;
propyl 4-pyridyl ketone;
4-cyanopyridine; and 4-pyridyl thioacetate:
12. A method according to any preceding claim comprising providing at least one thrips behaviour-modifying compound of formula (I) in a holding device wherein the compound of formula (I) attracts thrips to the holding device.
13. A method according to claim 12 wherein the holding device includes a means for immobilising or killing thrips.
14. A method according to claim 12 or claim 13 wherein the holding device is selected from the group comprising a water trap, a sticky trap and a pheromone trap.
15. A method of preventing or minimising damage to plants caused by thrips comprising attracting thrips away from the plants by providing at least one thrips-attracting compound of formula (I) as defined in claim 1 or claim 2.
16. A method according to claim 15 wherein R2, R3, and R5 are all hydrogen and R4 is halogen.
17. A method according to claim 15 wherein R2, R3, R4 and R5 are all hydrogen.
18. A method according to any one of claims 15 to 17 wherein R1 is , and is as defined in claim 1.
19. A method according to claim 18 wherein R6 is straight or branched chain alkyl.
20. A method according to any one of claims 15 to 17 wherein R1 is and R6 is as defined in claim 1.
21. A method according to claim 20 wherein R6 is straight or branched chain alkyl.
22. A method according to any one of claims 15 to 17 wherein R1 is and R6 is as defined in claim 1.
23. A method according to claim 22 wherein R6 is straight or branched chain alkyl.
24. A method according to any claim 15 wherein the at least one thrips-attracting compound of formula (I) is selected from the group comprising:
methyl isonicotinate;
ethyl isonicotinate;
propyl isonicotinate;
isopropyl isonicotinate;
decyl isonicotinate;
ethyl 2-chloro-isonicotinate;
pyridine, 4-(1,3-dioxolan-2-yl);
di-isopropyl isonicotinamide;
4-formyl pyridine;
methyl 4-pyridyl ketone;
ethyl 4-pyridyl ketone; and propyl 4-pyridyl ketone.
methyl isonicotinate;
ethyl isonicotinate;
propyl isonicotinate;
isopropyl isonicotinate;
decyl isonicotinate;
ethyl 2-chloro-isonicotinate;
pyridine, 4-(1,3-dioxolan-2-yl);
di-isopropyl isonicotinamide;
4-formyl pyridine;
methyl 4-pyridyl ketone;
ethyl 4-pyridyl ketone; and propyl 4-pyridyl ketone.
25. A method according to any one of claims 15 to 24 wherein the plants are selected from the group comprising onions, lettuce, cabbage and other crucifers, greenhouse vegetables, greenhouse fruits, flower crops and any other economically important plants that suffer from thrips infestations.
26. A method of preventing or minimising damage to plants caused by thrips, comprising repelling thrips away from the plants by providing at least one thrips-repelling compound of formula (I) as defined in claim 1 or claim 2.
27. A method according to claim 26 wherein R1 is CN.
28. A method according to claim 26 wherein R1 is and R6 is as defined in claim 1.
29. A method according to claim 28 wherein R6 is hydrogen or straight or branched chain alkyl.
30. A method according to claim 26 wherein R1 is and R6 is as defined in claim 1.
31. A method according to claim 30 wherein R6 is straight or branched chain alkyl.
32. A method according to claim 26 wherein the at least one thrips-repelling compound of formula (I) is selected from the group comprising:
4-formyl pyridine;
4-cyanopyridine; and 4-pyridyl thioacetate.
4-formyl pyridine;
4-cyanopyridine; and 4-pyridyl thioacetate.
33. A method according to any one of claims 26 to 34 wherein the plants are selected from the group comprising onions, lettuce, cabbage and other crucifers, greenhouse vegetables, greenhouse fruits, flower crops and any other economically important plants that suffer from thrips infestations.
34. A method of controlling, surveying or regulating thrips populations comprising providing at least one thrips-attracting compound of formula (I) as defined in claim 1 and at least one thrips-repelling compound of formula (I) as defined in claim 1.
35. A method of controlling, surveying or regulating thrips populations comprising providing at least one thrips-attracting compound of formula (I) as defined in claim 2 and at least one thrips-repelling compound of formula (I) as defined in claim 2.
36. A method according to claim 34 or claim 35 wherein the at least one thrips-attracting compound of formula (I) is as defined in any one of claims 3 to 11.
37. A method according to claim 34 or claim 35 wherein the at least one thrips-repelling compound of formula (I) is as defined in any one of claims 27 to 32.
38. A method according to claim 34 or claim 35 wherein the at least one thrips-attracting compound is selected from the group comprising;
methyl isonicotinate, ethyl isonicotinate, propyl isonicotinate, isopropyl isonicotinate, decyl isonicotinate, ethyl 2-chloro-isonicotinate, pyridine, 4-(1,3-dioxolan-2-yl), di-isopropyl isonicotinamide, 4-formyl pyridine, methyl 4-pyridyl ketone;, ethyl 4-pyridyl ketone and propyl 4-pyridyl ketone;
and the at least one thrips-repelling compound is selected from the group comprising;
4-formyl pyridine, 4-cyanopyridine and 4-pyridyl thioacetate.
methyl isonicotinate, ethyl isonicotinate, propyl isonicotinate, isopropyl isonicotinate, decyl isonicotinate, ethyl 2-chloro-isonicotinate, pyridine, 4-(1,3-dioxolan-2-yl), di-isopropyl isonicotinamide, 4-formyl pyridine, methyl 4-pyridyl ketone;, ethyl 4-pyridyl ketone and propyl 4-pyridyl ketone;
and the at least one thrips-repelling compound is selected from the group comprising;
4-formyl pyridine, 4-cyanopyridine and 4-pyridyl thioacetate.
39. A method of controlling, surveying or regulating thrips populations comprising providing at least one thrips behaviour-modifying compound of formula (I) as defined in claim 1 or claim 2 and at least one other thrips attractant or thrips repellant.
40. A method according to claim 39 wherein the at least one other thrips attractant or thrips repellant is selected from the group comprising:
ethyl nicotinate, anisaldehyde, cinnamaldehyde, methyl anthranilate, ethyl anthranilate, decyl acetate, dodecyl acetate, eugenol, beta-ionone, o-methoxy cinnamic aldehyde, methyl salicylate, ethyl salicylate, monoterpene 1,8-cineole, salicaldehyde, o-aminoacetophenone, isobornyl valerate, methyl benzoate, ethyl benzoate, 2-phenyl ethanol and p-allyl anisole.
ethyl nicotinate, anisaldehyde, cinnamaldehyde, methyl anthranilate, ethyl anthranilate, decyl acetate, dodecyl acetate, eugenol, beta-ionone, o-methoxy cinnamic aldehyde, methyl salicylate, ethyl salicylate, monoterpene 1,8-cineole, salicaldehyde, o-aminoacetophenone, isobornyl valerate, methyl benzoate, ethyl benzoate, 2-phenyl ethanol and p-allyl anisole.
41. A method according to any preceding claim wherein the thrips populations are those belonging to the sub-order Terebrantia.
42. A method according to claim 41 wherein the thrips populations are Thrips obscuratus, Thrips tabaci or Frankliniella occidentalis.
43. A holding device for catching, immobilising or killing thrips wherein the device contains a thrips behaviour-modifying compound of formula (I) as defined in claim 1 or claim 2.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NZ52949503 | 2003-11-13 | ||
| NZ529495 | 2003-11-13 | ||
| PCT/NZ2004/000285 WO2005046330A1 (en) | 2003-11-13 | 2004-11-12 | Insect behaviour modifying compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2545076A1 true CA2545076A1 (en) | 2005-05-26 |
| CA2545076C CA2545076C (en) | 2012-08-28 |
Family
ID=34588197
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2545076A Expired - Lifetime CA2545076C (en) | 2003-11-13 | 2004-11-12 | Insect behaviour modifying compounds |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US8962003B2 (en) |
| EP (1) | EP1691610B1 (en) |
| JP (2) | JP4927553B2 (en) |
| AU (1) | AU2004289152B8 (en) |
| CA (1) | CA2545076C (en) |
| ES (1) | ES2575089T3 (en) |
| NZ (1) | NZ546930A (en) |
| PL (1) | PL1691610T3 (en) |
| WO (1) | WO2005046330A1 (en) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8962003B2 (en) * | 2003-11-13 | 2015-02-24 | The New Zealand Institute For Plant And Food Research Limited | Insect behaviour modifying compounds |
| US8874477B2 (en) | 2005-10-04 | 2014-10-28 | Steven Mark Hoffberg | Multifactorial optimization system and method |
| JP4836763B2 (en) * | 2006-12-01 | 2011-12-14 | 大洋香料株式会社 | Thrips control agent |
| CN101861094B (en) * | 2007-09-25 | 2016-01-06 | 关键基因股份有限公司 | Plant volatiles |
| CN102340990B (en) * | 2009-03-05 | 2015-03-04 | 关键基因股份有限公司 | Plant volatiles based on R-curcumene |
| JP5115762B2 (en) * | 2010-02-12 | 2013-01-09 | 有機合成薬品工業株式会社 | Process for producing 4-formylpiperidine acetal derivative |
| TW201601629A (en) | 2013-10-02 | 2016-01-16 | Kyoyu Agri Co Ltd | Composition comprising harmful arthropod-attracting substance formed from plant-derived components and analogs thereof |
| CN104067988B (en) * | 2014-06-25 | 2016-09-07 | 云南农业大学 | A kind of study the insecticide olfactometer to long-stalked crops olfactory sensation orientation behaviour |
| JPWO2016009981A1 (en) * | 2014-07-17 | 2017-04-27 | 協友アグリ株式会社 | Combination of harmful arthropod-attracting compounds and natural enemies |
| CN104381255B (en) * | 2014-11-02 | 2018-06-05 | 浙江省农业科学院 | A kind of reagent for being used to lure Frankliniella occidentalis |
| WO2016159214A1 (en) * | 2015-04-01 | 2016-10-06 | 協友アグリ株式会社 | Combination of harmful-arthropod attracting compound and harmful-arthropod repelling compound |
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| JP6871802B2 (en) * | 2016-07-28 | 2021-05-12 | エヌ・イーケムキャット株式会社 | A method for obtaining a carbonyl compound by a carbonylation reaction of a halogen compound using an aldehyde as a carbon monoxide source in the presence of a heterogeneous palladium catalyst. |
| KR102580718B1 (en) * | 2020-03-06 | 2023-09-21 | 이동하 | Attractants of Yellow Tea Trips |
| CN115336582B (en) * | 2022-08-17 | 2023-05-02 | 中国农业科学院植物保护研究所 | Thrips lure device and control method |
| CN116114515B (en) * | 2023-01-10 | 2024-10-01 | 福建省农业科学院植物保护研究所 | Method for controlling thrips pests by utilizing combination of trapping plants, pesticides and repellents |
| WO2025046378A1 (en) * | 2023-09-01 | 2025-03-06 | Indian Council Of Agricultural Research (Icar) | Bacterial-based volatiles composition as jassid attractant |
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| GB347451A (en) | 1929-04-04 | 1931-04-30 | I.G. Farbenindustrie Aktiengesellschaft | |
| US2889330A (en) * | 1955-08-24 | 1959-06-02 | Monsanto Chemicals | Pyridylethyl thiophosphates |
| GB1059990A (en) * | 1964-12-18 | 1967-02-22 | Ici Ltd | Substituted pyridines |
| JPS5026451B2 (en) * | 1972-10-03 | 1975-09-01 | ||
| DE3703212A1 (en) * | 1987-01-30 | 1988-08-11 | Schering Ag | 2- (2,2-DIFLUORCYCLOPROPYL) -ALKYLESTER, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS AN INSECTICIDE AND ACARICIDAL AGENT |
| JPH082767B2 (en) | 1987-08-01 | 1996-01-17 | 大洋香料株式会社 | Pest repellent |
| JPH01261303A (en) * | 1988-04-13 | 1989-10-18 | Taiyo Koryo Kk | Insect pest repellent |
| JP2602912B2 (en) * | 1988-08-11 | 1997-04-23 | 学校法人近畿大学 | Composition for controlling Thrips palmi Karny and control method |
| JP2994182B2 (en) * | 1992-07-23 | 1999-12-27 | 石原産業株式会社 | Amide compounds or salts thereof, methods for producing them and pest control agents containing them |
| JPH0710841A (en) * | 1993-06-21 | 1995-01-13 | Ishihara Sangyo Kaisha Ltd | 4-trifluoromethylpyridine-3-carboxamide compound or salt thereof, their production and pest-controlling agent containing the same |
| TW307746B (en) | 1994-10-14 | 1997-06-11 | Sumitomo Chemical Co | |
| JP3835125B2 (en) * | 1994-10-14 | 2006-10-18 | 住友化学株式会社 | Dihalopropene compound, its use and production intermediate |
| JP3106928B2 (en) * | 1994-10-14 | 2000-11-06 | 住友化学工業株式会社 | Dihalopropene compounds, their uses and their production intermediates |
| JPH08256658A (en) * | 1995-03-28 | 1996-10-08 | Sumitomo Chem Co Ltd | Pest trap |
| CR6574A (en) | 2001-02-27 | 2004-10-28 | Syngenta Participations Ag | SALTS OF SUBSTITUTED FINDINGS IN POSITION 4 WITH PESTICIATED PROPERTIES |
| JP2003146971A (en) * | 2001-11-07 | 2003-05-21 | Sumitomo Chem Co Ltd | Pyridine compounds and their uses |
| GB0130577D0 (en) * | 2001-12-21 | 2002-02-06 | Univ Keele | Method of monitoring/controlling thysanoptera |
| US8962003B2 (en) * | 2003-11-13 | 2015-02-24 | The New Zealand Institute For Plant And Food Research Limited | Insect behaviour modifying compounds |
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- 2004-11-12 AU AU2004289152A patent/AU2004289152B8/en not_active Expired
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| CA2545076C (en) | 2012-08-28 |
| JP2007511506A (en) | 2007-05-10 |
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| EP1691610A1 (en) | 2006-08-23 |
| JP4927553B2 (en) | 2012-05-09 |
| US8962003B2 (en) | 2015-02-24 |
| NZ546930A (en) | 2010-09-30 |
| PL1691610T3 (en) | 2016-09-30 |
| EP1691610B1 (en) | 2016-03-09 |
| WO2005046330A1 (en) | 2005-05-26 |
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