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EP-4739112-A1 - PESTICIDAL METHODS AND COMPOSITIONS

EP4739112A1EP 4739112 A1EP4739112 A1EP 4739112A1EP-4739112-A1

Abstract

The present disclosure relates generally to methods and uses for controlling pests. More particularly, the present disclosure relates to methods and uses for controlling pests in a covered environment, comprising exposing said pests to an effective amount of a vapour form of a compound of formula (I) as defined herein. Also described are pesticidal compositions, kits comprising a compound of formula (I) and a diffuser, diffusers and refill vessels for diffusers.

Inventors

  • MAY, PETER
  • WADE, JAMES

Assignees

  • Bio-Gene Technology Limited

Dates

Publication Date
20260513
Application Date
20240703

Claims (20)

  1. The claims defining the invention are as follows: 1. A method for controlling pests in a covered environment, comprising exposing said pests in said covered environment to an effective amount of a vapour form of a compound of formula (I): 2 O R 6 R 5 wherein R 1 is selected from –C(=O)R 7 , -OR 8 , -SR 8 , -C 1-10 hydroxyalkyl, -NR 9 R 10 , -C(=N- R 9 )R 7 , -C(=N-OH)R 7 , -NO, -NO 2 , -N(OR 8 )R 7 and –OSO 3 R 8 ; R2 is selected from hydrogen, -C1-10alkyl, -C2-10alkenyl, aryl and heteroaryl; R 3 , R 4 , R 5 and R 6 are each independently selected from hydrogen, -C 1-10 alkyl, -C 3- 6 cycloalkyl, -C 2-10 alkenyl, -C 1-10 haloalkyl, -C 1-10 dihaloalkyl, -C 1- 10trihaloalkyl, -OR8, -SR8, -NR9R10, -C(=N-R9)R7, -NO, -NO2, -NR9OR8, -OSO3R8, -C1- 10alkylaryl and –C(=O)R7; R 7 is selected from hydrogen, -C 1-10 alkyl, -C 2-10 alkylaryl, C 3-6 cycloalkyl, -C 2- 10alkenyl, -C1-10alkylheteroaryl, -C1-10haloalkyl, -C1-10dihaloalkyl, -C1-10trihaloalkyl, -C1- 10haloalkoxy, -C1-10hydroxyalkyl, -C1-10thioalkyl, -C1-10nitroalkyl, -C1-3alkylOC1-3alkyl, - C 1-3 alkylOC 1-3 haloalkyl, -C 1-3 alkylOC 1-3 dihaloalkyl, -C 1-3 alkylOC 1-3 trihaloalkyl, -OR 8 , - SR 8 and –NR 9 R 10 ; R8 is selected from hydrogen, -C1-10alkyl, -C2-10alkylaryl, -C3-6cycloalkyl, -C2- 10 alkenyl, -C 1-10 alkylheteroaryl, -C 1-10 haloalkyl, -C 1-10 dihaloalkyl, -C 1-10 trihaloalkyl, -C 1- 10 haloalkoxy, -C 1-10 hydroxyalkyl, -C 1-10 thioalkyl and -C 1-10 nitroalkyl; and R9 and R10 are independently selected from hydrogen, -C1-10alkyl, -C2-10alkylaryl, -C3-6cycloalkyl, -C2-10alkenyl, -C1-10alkylheteroaryl, -C1-10haloalkyl, -C1-10dihaloalkyl, - C 1-10 trihaloalkyl.
  2. 2. The method according to claim 1, wherein the compound of formula (I) is a compound of formula (II): 11 O ) wherein R11 is selected from –CR12R13R14 or –NR15R16; one of R12 and R13 is hydrogen and the other is hydroxyl or –OCR17R18R19 or R12 and R 13 together form an oxo group (=O) or a =N-OH group; R14 is –CH(CH3)CR20R21R22, -CH2CH(CH3)CR20R21R22 or – CH(CH3)CH2CR20R21R22; R 15 and R 16 are independently selected from hydrogen and C 1-10 alkyl; R 17 , R 18 and R 19 are independently selected from hydrogen or halo; and R20, R21 and R22 are independently selected from hydrogen, hydroxyl, halo, NO2 and –OCR17R18R19.
  3. 3. The method according to claim 1, wherein the compound of formula (I) is a compound of formula (III): R 25 R 26 O ) wherein one of R23 and R24 is hydrogen and the other is hydroxyl or –OCR27R28R29 or R23 and R24 together form an oxo group (=O); R 25 is –CR 30 R 31 R 32 , -CH 2 CR 30 R 31 R 32 or –CH(CH 3 )CR 30 R 31 R 32 ; R26 is H or –CH3; wherein where R26 is H, R25 is –CH(CH3)CR30R31R32; R27, R28 and R29 are independently selected from hydrogen or halo; and R 30 , R 31 and R 32 are independently selected from hydrogen, hydroxyl, halo, NO 2 and –OCR 27 R 28 R 29 .
  4. 4. The method according to claim 1, wherein the compound of formula (I) is selected from the group consisting of: 2F O CBr 3 O OCH 3 O O N O O CH 2 F O CBr 3 O OCH 3 O O N O O CH 2 F O CBr 3 O 2 OCH 3 O O .
  5. 5. The method according to any one of claims 1 to 4, wherein the compound of formula (I) is selected from the group consisting of flavesone, leptospermone, isolpetospermone, papuanone, grandiflorone and jensenone.
  6. 6. The method according to claim 5, wherein the compound of formula (I) is flavesone.
  7. 7. The method according to any one of claims 1 to 6, wherein the compound of formula (I) is applied to the covered environment at a rate of 0.5 ng/hr to 500 mg/hr or 0.5 µg/hr to 250 mg/hr or from 0.5 mg/hr to 125 mg/hr or 0.5 pL/hr to 500 µL/hr or 0.5 nL/hr to 250 µL/hr or 0.5 µL/hr to 250 µL/hr, per m 3 of space defining the environment.
  8. 8. The method according to any one of claims 1 to 7, wherein the compound of formula (I) is applied to the covered environment using a single release point per at least about 6 m 3 of the volume of space defining the environment.
  9. 9. The method according to any one of claims 1 to 8, wherein the compound of formula (I) is applied to the covered environment using a diffuser.
  10. 10. The method according to any one of claims 1 to 9, wherein the diffuser is temperature and/or a mechanical diffuser.
  11. 11. The method according to any one of claims 1 to 10, wherein the diffuser is an electric diffuser.
  12. 12. The method according to claim any one of claims 1 to 11, wherein the compound of formula (I) is applied to the covered environment using a dispersing aid.
  13. 13. The method according to any one of claims 1 to 12, wherein the compound of formula (I) is used in combination with at least one second pesticide.
  14. 14. The method according to claim 13, wherein the at least one second pesticide is selected from the group consisting of a sodium channel modulator, an acetylcholinesterase (AChE) inhibitor, a GABA-gated chloride channel antagonist, a nicotinergic acetylcholine receptor agonist, an allosteric acetylcholine receptor modulator, a chloride channel actuator, a juvenile hormone mimic, a homopteran feeding blocker, a mitochondrial ATP synthase inhibitor, an uncoupler of oxidative phosphorylation, a nicotinic acetylcholine receptor channel blocker, an inhibitor of chitin biosynthesis, a moulting disruptor, an ecdysone receptor agonist or disruptor, an octapamine receptor agonist, a mitochondrial complex I electron transport inhibitor, an acetyl CoA carboxylase inhibitor, a voltage-dependent sodium channel blocker, a mitochondrial complex IV electron inhibitor, a mitochondrial complex IV electron transport inhibitor or a ryanodine receptor modulator.
  15. 15. The method according to claim 14, wherein the at least one second pesticide is a sodium channel modulator, preferably a pyrethroid and/or pyrethrin, more preferably pyrethrin I, pyrethrin II, metofluthrin, transfluthrin and/or prallethrin.
  16. 16. The method according to any one of claims 13 to 15, wherein the compound of formula (I), the at least one second pesticide, or both the compound of formula (I) and the at least one second pesticide, are used in a sub-effective amount.
  17. 17. The method according to any one of claims 13 to 16, wherein the compound of formula (I), the at least one second pesticide, or both the compound of formula (I) and the at least one second pesticide, are used in a sub-additive amount.
  18. 18. The method according to any one of claims 1 to 17, wherein the pest is a flying insect.
  19. 19. The method according to claim 18, wherein the pest is an insect of the order Diptera.
  20. 20. The method according to claim 19, wherein the insect is a Musca species, Aedes species, Anopheles species, or a Culex species.

Description

PESTICIDAL METHODS AND COMPOSITIONS RELATED APPLICATION [0001] This application claims the benefit of Australian provisional patent application number 2023902139, filed 3 July 2023, the entire contents of which is incorporated herein by reference. FIELD OF THE DISCLOSURE [0002] The present disclosure relates generally to methods and uses for controlling pests. More particularly, the present disclosure relates to methods and uses for controlling pests in a covered environment, comprising exposing said pests to an effective amount of a vapour form of a compound of formula (I) as defined herein. Also described are pesticidal compositions, kits comprising a compound of formula (I) and a diffuser, diffusers and refill vessels for diffusers. BACKGROUND OF THE DISCLOSURE [0003] Effective pest control is important across many industries, not least of all in agriculture in the production of food and livestock. For instance, insect infestation arising from ineffective insect control can result in complete destruction of a stored crop harvest, or contamination of the harvest and food production lines, with the associated health concerns for animal and human consumers, including through the spread of disease and infection. Arthropod vector-borne diseases can also spread rapidly through animal populations, especially those relying on animal houses, resulting in losses and potentially decimation of the animal population. Domestic and industrial insect control is similarly important to mitigate the spread of insect-borne infection and diseases and for good hygiene practices. [0004] Arthropod vectors, including the mosquito vectors of dengue, malaria and filariasis, and fly species such as sand and filth flies that transmit diseases such as leishmaniasis, enteric and helminth infections, remain significant public health pests worldwide. [0005] With the rising threat from pesticide resistant vectors and global environmental change there is an increasing need to incorporate more pest control interventions to reduce the spread of, or eliminate, these diseases, to protect harvests, avoid contamination of food production lines, and for good hygiene practices. There is also a need to improve current pest control tools and advance the development of pest control products based on new paradigms, including those that function through alternative mechanisms of action. [0006] Resistance development to pyrethroids is a particular ongoing concern. The implications are a decrease in the effectiveness of pyrethroids in pest control, requiring greater quantities of pyrethroids to be used for comparable control with a net increase in risk of pest resurgence, product cost and possible damage risks to individuals, commodities and the environment. [0007] It would be desirable to provide improved pest control methods to address at least one of the problems above and/or which may provide further pest management options for users. SUMMARY OF THE DISCLOSURE [0008] In one aspect, the present disclosure provides a method for controlling pests in a covered environment, comprising exposing said pests in said covered environment to an effective amount of a vapour form of a compound of formula (I): 2 O R6 R5 wherein R1 is selected from –C(=O)R7, -OR8, -SR8, -C1-10hydroxyalkyl, -NR9R10, -C(=N- R9)R7, -C(=N-OH)R7, -NO, -NO2, -N(OR8)R7 and –OSO3R8; R2 is selected from hydrogen, -C1-10alkyl, -C2-10alkenyl, aryl and heteroaryl; R3, R4, R5 and R6 are each independently selected from hydrogen, -C1-10alkyl, -C3- 6cycloalkyl, -C2-10alkenyl, -C1-10haloalkyl, -C1-10dihaloalkyl, -C1- 10trihaloalkyl, -OR8, -SR8, -NR9R10, -C(=N-R9)R7, -NO, -NO2, -NR9OR8, -OSO3R8, -C1- 10alkylaryl and –C(=O)R7; R7 is selected from hydrogen, -C1-10alkyl, -C2-10alkylaryl, C3-6cycloalkyl, -C2- 10alkenyl, -C1-10alkylheteroaryl, -C1-10haloalkyl, -C1-10dihaloalkyl, -C1-10trihaloalkyl, -C1- 10haloalkoxy, -C1-10hydroxyalkyl, -C1-10thioalkyl, -C1-10nitroalkyl, -C1-3alkylOC1-3alkyl, - C1-3alkylOC1-3haloalkyl, -C1-3alkylOC1-3dihaloalkyl, -C1-3alkylOC1-3trihaloalkyl, -OR8, - SR8 and –NR9R10; R8 is selected from hydrogen, -C1-10alkyl, -C2-10alkylaryl, -C3-6cycloalkyl, -C2- 10alkenyl, -C1-10alkylheteroaryl, -C1-10haloalkyl, -C1-10dihaloalkyl, -C1-10trihaloalkyl, -C1- 10haloalkoxy, -C1-10hydroxyalkyl, -C1-10thioalkyl and -C1-10nitroalkyl; and R9 and R10 are independently selected from hydrogen, -C1-10alkyl, -C2-10alkylaryl, -C3-6cycloalkyl, -C2-10alkenyl, -C1-10alkylheteroaryl, -C1-10haloalkyl, -C1-10dihaloalkyl, - C1-10trihaloalkyl. [0009] In another aspect, there is provided the use of a compound of formula (I) as defined herein, for controlling pests in a covered environment, wherein said pests are exposed to an effective amount of a vapour form of said compound of formula (I) in said covered environment. [0010] In another aspect, there is provided a diffuser containing a compound of formula (I) as defined herein. [0011] In another aspect, there is provided a refill vessel containing a c