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
  • A01N49/00—Biocides, pest repellants or attractants, or plant growth regulators, containing compounds containing the group, wherein m+n>=1, both X together may also mean —Y— or a direct carbon-to-carbon bond, and the carbon atoms marked with an asterisk are not part of any ring system other than that which may be formed by the atoms X, the carbon atoms in square brackets being part of any acyclic or cyclic structure, or the group, wherein A means a carbon atom or Y, n>=0, and not more than one of these carbon atoms being a member of the same ring system, e.g. juvenile insect hormones or mimics thereof
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
  • C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
  • C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond

Definitions

• the present invention relates to a method of monitoring or controlling Thysanoptera (thrips), particularly but not exclusively Thripinae, particularly Thrips palmi (Karny). INTRODUCTION
• Thysanoptera is a group of insects that is recognised as causing damage to a wide range of cultivated crops.
• Some thrips are a pest of a particular crop, e.g. avocado thrips are a pest to avocado crops, whereas some species are a pest to a wide range of crops. Thrips cause damage to crops by feeding upon the crops and laying their eggs therein.
• Their feeding method comprises penetrating parts of the plant and sucking out the liquid contents, thus causing aesthetically unappealing scarring and stunting the growth of the crop.
• the presence of insects alone or small feeding marks can make ornamental crops unsaleable.
• Thrips are commonly active within enclosed parts of the crop, such as flower buds and leaf buds.
• the damage caused by thrips in the form of direct damage such as feeding and in the form of indirect damage such as transmission of a virus, occurs before the thrips themselves are observed.
• the management of thrips is a particularly acute problem because the thrips damage is sometimes only observed in the late stages of flower development when the bud finally opens.
• Thrips are also a problem because they breed rapidly and large pest populations can build up very quickly if unchecked.
• Thrips palmi a member of the Thripinae sub-family.
• the pest targets a large range of crops including many crops found in the EU (Cannon et al., 2007a).
• the significant danger posed by the pest is reflected in its presence on the A1 list of species recommended for regulation as quarantine pests by the European and Mediterranean Plant Protection Organisation, and its presence in Annex IAI of the EC Plant Health Directive (2000/29/EC), which specifies that the pest must be eradicated wherever it appears in the EU.
• T. pa/m/ ' outbreaks have already occurred in numerous places across the world, such as Japan and Australia.
• T. palmi During the post-invasion phase in Japan by T. palmi, over 9000 ha of greenhouse vegetable crops were affected with 30% of aubergine crops being lost (Nagai, 1993).
• T. palmi remains a major pest in several greenhouse and outdoor crops in Japan (Kawai, 2001 ; Yano, 2004).
• horticultural exports dropped by 71 % from €3.0m to €1.1 m as a result of crop losses and quarantine restrictions.
• insects One method of controlling insects is the direct application of pest control agents/pesticides to the plant/crop.
• pest control agents/pesticides are commonly toxic to other animals their use is becoming increasingly less acceptable on environmental and ecological grounds.
• undesirable reactions such as poisoning or allergies, for agricultural and horticultural workers.
• Many consumers are reluctant to purchase edible crops that have been treated with pesticides, because of fears of adverse effects on their health from pesticide residues.
• Thrips are particularly difficult to control with insecticides because they retreat into minute recesses on the plant where insecticides are less likely to reach them and because the main pest species have high levels of insecticide resistance. Additionally pesticides applied to crops are perceived to be a poor solution to the problem of thrips since the pesticides used are normally detrimental to the population of beneficial arthropods that prey upon the thrips and other insect and mite pests on the crop.
• An alternative method of controlling insects is to use biological control agents.
• Biological control agents such as predatory mites or fungal pathogens are sometimes used to control thrips, but they are not always reliable and they are not very effective on some crops.
• a further method for controlling insects involves the use of insect traps.
• the use of traps in the vicinity of the crop that contain a semiochemical (such as an aggregation pheromone) and a pest control agent (such as glue, insecticide, or biocide) is becoming increasingly widespread.
• the traps may be selective in attracting one sex (usually the male) of the insect concerned so as to remove them from the population and hence control population growth.
• the traps may be more general in their operation.
• the general release of an attracting sex pheromone is also sometimes used as a control method.
• the released sex pheromone "confuses" the sex that is attracted so that it cannot locate a mate. This disruption of the mating process slows down or stops the build-up of the pest population.
• male thrips form mating aggregations whilst producing aggregation pheromones which cause numbers of males and females in the area to grow.
• the male thrips do not store aggregation pheromones, and instead produce them when required in very small (picogram) quantities.
• pheromones and other semiochemicals differ from species to species, meaning that compounds which affect the behaviour of one species are most likely to have no effect upon other species, or possibly an entirely different effect.
• Thripline ams One such product, is marketed under the name “Thripline ams” by Syngenta Bioline. This product is based on neryl (S)-2-methylbutanoate, which has been discovered to be an aggregation pheromone released by male western flower thrips, increasing trap catches of males and females in glasshouses.
• Another semiochemical-based product targeting western flower thrips, as well as other species, is offered by Koppert B.V. under the name “LUREM-TR”, and methyl isonicotinate is the current active ingredient.
• the present invention provides a method of monitoring or controlling Thysanoptera (hereafter thrips) using a behaviour-modifying compound of Formula (1), wherein Formula (1) is:
• R is a C 2 -C 8 straight or branched alkenyl group and the * denotes a stereocentre.
• alkenyl group we mean a univalent aliphatic hydrocarbon radical having at least one carbon-carbon double bond. All structural isomers (including positional isomers) and stereoisomers (including cis and trans (Zand E) isomers) are encompassed within the term "alkenyl”.
• the double bond may be at the terminal position of the alkenyl moiety, or may occur at some other part of the alkenyl moiety.
• a "Cn alkenyl” group means an alkenyl group having n carbon atoms.
• the present inventors have found through extensive research that compounds of Formula (1) are particularly effective in replicating or mimicking the effects of a natural thrips pheromone and thus may be effectively used in methods of monitoring or controlling the behaviour of thrips.
• the compounds are aggregation pheromones (i.e., attractants) of thrips, in particular, T. palmi.
• the compounds attract both male and female thrips.
• the present invention does not rely on any toxic qualities of the compound of Formula (1) but rather on the modification of thrips behaviour for its effect.
• controlling thrips includes activities such as attracting, confusing, killing and / or modifying the behaviour of thrips.
• monitoring is also intended to cover a number of activities, including determining the number of thrips in a region and / or identifying the species of thrips in a region, including identifying the relative changes in the numbers of thrips in a region.
• the method of monitoring or controlling thrips can be carried out in several ways.
• the method involves providing the behaviour-modifying compound at a pre-determined location.
• the behaviour-modifying compound is released or broadcast within an area infested (or potentially infested) by thrips. This can be achieved by using a lure or other release device comprising a compound of Formula (1), for example to attract the thrips to a trap. Suitable release devices and traps are discussed below.
• the ability to monitor the type (i.e., species) and number of thrips is an important advantage in establishing the threat posed by thrips and it can provide an early warning as to rising thrips numbers. Improved monitoring using a compound according to Formula (1) as an attractant or pheromone can therefore lead to more effective treatment of thrips, for example by early treatment.
• the method is for monitoring male and / or female thrips.
• the method is for monitoring adult male and / or adult female thrips.
• the method may be used to gauge the population density of thrips in a particular area from analysis of the number and / or sex of the thrips. Based on the number of thrips monitored a decision may then be made as to what further action, if any, is required. The level of monitoring or controlling may be selected so that as high a portion of thrips is removed from the population as possible. When female thrips are monitored or controlled, management of the overall thrips population can be achieved by reducing the number of female thrips.
• the method uses a compound where R is a branched alkenyl group.
• the method uses a compound where R is C 2 to C 7 , more preferably C 3 to C 7 , more preferably C 3 to C 6 , more preferably C 3 to C 5 , more preferably C 3 to C 4 , most preferably C 4 .
• the method uses a compound where R is a branched C 4 alkenyl group.
• R comprises one carbon-carbon double bond.
• R comprises a carbon-carbon double bond at a terminal position of the alkenyl group.
• the behaviour-modifying compound is not (S)-lavandulyl senecioate (which is also known by the systematic name of (S)-lavandulyl 3-methyl-2-butenoate).
• the stereocentre marked with a "*" in Formula (1) can take either an (R) configuration or an (S) configuration, leading to molecules referred to herein as the "(R) stereoisomer” and "(S) stereoisomer".
• the compound used in methods of the present invention is part of a racemic mixture of (R) and (S) stereoisomers. In other embodiments, the compound is predominantly present in one stereoisomeric form.
• the compound is present in a composition where there is an excess of the (R) stereoisomer relative to the (S) stereoisomer.
• the amount of the (R) stereoisomer as a percentage of the total amount of the compound of Formula (1 ) present may be greater than 60%, greater than 70%, or greater than 80%. Preferably this percentage is greater than 90%, more preferably greater than 95% and most preferably about 100%.
• the percentage enantiomeric excess of the (R) stereoisomer is greater than 0%, more preferably greater than 25%, more preferably greater than 50%, still more preferably greater than 75%, and most preferably about 100%.
• the R group also contains a stereocentre then diastereomers are also possible.
• lavandulyl 3-methyl-3-butenoate which is a compound according to Formula (2):
• the present inventors have found that the compound shown in Formula (3) is released naturally from T. palmi, a member of the Thripinae sub-family of thrips.
• methods using a compound of Formula (3) allow replication of the effects of a natural thrips pheromone.
• the compound is produced in extremely small amounts by the male insects, and thus the identification and characterisation of the molecule presented considerable technical challenges and hurdles.
• the compound shares some general structural similarities with neryl (S)-2-methylbutanoate, an aggregation pheromone of western flower thrips. This, and its presence only in the males and not the females, provides strong evidence that the compound of Formula (3) is an aggregation pheromone for T. palmi. Furthermore, experimental data presented below show that the compound significantly improves trap catches of T. palmi. In other words, the compound is an attractant for T. palmi. Thus, in preferred embodiments, the methods of the present invention are for monitoring or controlling T. palmi.
• the methods of the present invention are for monitoring or controlling F. intonsa. More generally, it is preferred that methods of the present invention are for monitoring or controlling thrips from the family Thripidae, most preferably from the sub-family Thripinae.
• the behaviour-modifying compound is a thrips aggregation pheromone, i.e., an attractant.
• an attractant i.e., an attractant.
• the compound attracts both males and females.
• the use of a behaviour-modifying compound of Formula (1) as an attractant preferably improves the sensitivity of traps for thrips, particularly at low levels of infestation or in easily damaged crops in glasshouses.
• the compound can be used to attract thrips away from a crop. Methods in which the compound is used as an attractant allow growers to identify the pest and introduce additional control measures before pest populations reach economically damaging levels.
• the behaviour-modifying compound is used as a confusant.
• confusant compounds in an area infested (or potentially infested) with thrips, the effect of the natural pheromones released by the thrips may be overcome or "masked” such that the thrips become “confused".
• a "cloud" of the compound may be provided around a thrips such that the thrips is unable to find the source of the compound. In this way, the thrips may move in a random way.
• the compound can increase the activity of a thrips so as to increase the likelihood of the thrips encountering a thrips killing device or thrips monitoring device, or a pesticide or biological control agent.
• the present inventors have found that the behaviour-modifying effect of compounds of Formula (1) can be achieved for extended periods of time by controlling the release of the compounds into the air.
• a release device is adapted to release a pheromone such as compounds of Formula (1) into the air.
• the release device actively releases the compound into the air (e.g., spraying the compound into the air).
• the release device passively releases the compounds into the air (e.g., by evaporation).
• the release device can have a mechanism for releasing the compound into the air and also allow compounds to be passively released.
• the compound can be actively or passively dispersed or broadcast in a particular area
• a release device includes arrangements wherein the compound is released into the air for the purposes of changing the behaviour of thrips, for example by confusing them or randomising their movements, as well as arrangements wherein the compounds are released such that a thrips is attracted to and lands on the release device.
• Several types of release device are possible.
• the release device comprises a matrix and the compound of Formula (1) is dispersed within the matrix.
• the matrix is porous.
• the matrix is made of rubber, preferably natural rubber.
• the matrix may be made of materials other than rubber, for example plastics material such as polymers.
• the matrix is in the form of a septum, preferably a rubber septum, such as those available from International Pheromone Systems Ltd.
• the release device may be a laminate.
• the release device is a container having walls that are permeable to compounds of Formula (1), wherein the container contains a compound of Formula (1).
• the container therefore provides a reservoir of the behaviour-modifying compound and a means for controllably releasing the compound, i.e. via the permeable walls.
• the walls are flexible.
• the container is closed (or closable, for example with a closable opening) such that the compound can leave the container only via the walls.
• the flexible walls are made from a plastics material, preferably polyethylene.
• the container is a bag or sachet.
• the release device is a container, preferably a tube, which contains the behaviour-modifying compound, wherein the container comprises an orifice through which the compound can be released from the container.
• the container is closed (or closable, for example with a closable opening) such that the compound can leave the container only via an orifice.
• the diameter of the orifice can be adjusted to control the rate of release (typically via evaporation) of the compound.
• Suitable containers are Eppendorf tubes (centrifuge tubes) which have been adapted by providing an orifice in one of the walls of the tube.
• the release device is a sprayer.
• the sprayer allows an area of interest to be sprayed with the behaviour-modifying compound.
• the sprayer may be a backpack sprayer or a hand held plant sprayer.
• the sprayer may take the form of an elongate conduit with several spraying nozzles positioned along the conduit for releasing the behaviour-modifying compound.
• the sprayer may be an aerosol sprayer.
• the sprayer may be an aerosol can containing the behaviour-modifying compound and a propellant. In this way, the behaviour-modifying compound may be applied to a surface where it subsequently evaporates. Alternatively or additionally, the compound may be sprayed directly into the air.
• the release device is configured to produce or release a compound of Formula (1) in an amount which is at least and more preferably a multiple of the amount of pheromone which would be released by a single thrips.
• the release device releases an amount that is at least twice the amount produced by a single thrips, preferably at least four times, more preferably at least eight times, more preferably at least twenty times, and more preferably still at least eighty times the amount produced by a single thrips.
• the release rate is such that the concentration of behaviour- modifying compound in the immediate vicinity of the release device is greater than that produced by a single thrips, preferably at least four times, more preferably at least eight times, more preferably at least twenty times, and more preferably still at least eighty times the amount produced by a single thrips.
• the lower limit for the release rate from the release device can be, for example, 1 picogram per hour, 10 picograms per hour, 100 picograms per hour, 1000 picograms per hour or 2000 picograms per hour.
• the upper limit for the release rate is not particularly limited but can be, for example, 1.5 ⁇ 10 6 picograms per hour, 1 ⁇ 10 6 picograms per hour, 7.5 ⁇ 10 5 picograms per hour, 5 ⁇ 10 5 picograms per hour, 1 ⁇ 10 5 picograms per hour, 5 ⁇ 10 4 picograms per hour or 1 ⁇ 10 4 picograms per hour.
• preferred release rates include 1 to 1 ⁇ 10 picograms per hour, more preferably 1000 to 5 ⁇ 10 5 picograms per hour.
• the release suitably occurs from a surface of the release device having an associated surface area.
• the compound is released from the surface impregnated with the compound.
• the compound is released from a surface in contact with the air.
• the lower limit for the release rate of the compound, normalised to the area from which the compound is emitted is preferably 0.001 picograms per hour per cm 2 of surface area, 0.01 picograms per hour per cm 2 , 0.1 picograms per hour per cm 2 , 1 picogram per hour per cm 2 , or 10 picograms per hour per cm 2 .
• the upper limit for the release rate of the compound, normalised to the area from which the compound is emitted can be 10000 picograms per hour per cm 2 of surface area, 5000 picograms per hour per cm 2 , 2500 picograms per hour per cm 2 , or 1000 picograms per hour per cm 2 .
• the lower and upper limits for the release rate normalised to the area from which the compound is emitted can be combined together, and the present invention is intended to cover all such combinations.
• the preferred release rate may be dependent upon the way in which the behaviour-modifying compound is being used, e.g., whether it is being used as an attractant, to increase activity of thrips, or as a confusant.
• the release rate from sprayers in which the compound is actively released from the release device (as opposed to passively by, for example, evaporation) is determined by the user to suit the area in which the behaviour-modifying compound is released.
• the release device acts as a lure.
• a large number of lures are available commercially (for example, from Russell IPM).
• the thrips can be lured to a thrips monitoring device.
• the methods of monitoring or controlling thrips that form part of the present invention include methods of killing thrips. This can be achieved by luring the thrips to a thrips killing device.
• the compound is not acting as a pesticide or other toxic agent, but as an attractant and is suitably associated with a thrips killing device (e.g. a sticky trap or water trap). Additionally or alternatively to the compound attracting the thrips directly to a thrips killing device, suitably the compound can increase the activity of a thrips so as to increase the likelihood of the thrips encountering a thrips killing device.
• a thrips killing device e.g. a sticky trap or water trap.
• the release device is preferably associated with a thrips killing device for immobilising and / or killing the thrips.
• a release device associated with a thrips killing device may be used to attract thrips and then immobilise or kill the thrips so as to remove the thrips from a crop growing area.
• the thrips killing device is a trap.
• the trap comprises a substrate and a sticky adhesive coating applied to the substrate.
• the substrate is in the form of a sheet.
• the sheet is rectangular.
• the sheet has dimensions of about 5 to 10 cm by about 10 to 25 cm, although other dimensions and shapes are possible.
• the sticky adhesive coating may be applied to just one side of the sheet, or to both sides of the sheet.
• the substrate may also be in the form of an elongate strip.
• the sheet may be in the form of an elongate strip that can extend along, around or across a portion of the growing area. The elongate strip may be sold on a roll, from which it may be unwound.
• the trap may also comprise a mesh layer, for example having a mesh grid size of approximately 5mm x 5mm, which can assist handling.
• the substrate comprises a plastics material, but it can also be made of paper or other materials.
• the sticky adhesive coating is non-toxic. Such adhesive coatings or "insect glues" are known and are typically polymeric. Traps of this sort are known as sticky traps.
• the sticky trap may be a wet sticky trap, or may be a dry sticky trap such as a Takitrap® (available from Syngenta Bioline).
• the release device is integral with the trap.
• the trap is preferably also the release device.
• the substrate is porous to allow impregnation of the behaviour-modifying compound.
• the behaviour-modifying compound can be incorporated into the adhesive coating, e.g. by adding the compound directly to the adhesive coating or by formulating the adhesive with the compound prior to application to the substrate.
• the behaviour- modifying compound can be coated onto the substrate before an adhesive coating is applied.
• one or both of the substrate and the sticky adhesive layer can act as a matrix in which the behaviour-modifying compound is dispersed and from which it can evaporate under typical glasshouse, polytunnel, or open field conditions.
• the release device is not integral to the trap, and is instead a separate part.
• the trap comprises a container which in use is filled with water, or a mixture of water and detergent. When a thrips enters the trap, it will fall into the water-filled container and become immobilised on contact with the water.
• This type of trap is commonly known as a water trap.
• the release device is suspended above the container and / or attached to the container.
• the trap includes attachment means to which the release device can be attached.
• thrips are attracted to the trap and brought into proximity with the water, thereby increasing the chances of immobilising the thrips.
• This sort of trap is particularly preferred because large numbers of thrips can be trapped.
• a water trap can also be made in which the release device is integral with the trap.
• the trap and/or release device is coloured to attract thrips.
• the trap and/or release device is coloured blue, white or yellow or combinations of these and/or other colours.
• coloured release devices is described in the paper Journal of Applied Entomology, 107, 136-140 (H. F. Br0dsgaard), in which a sheet having a colour close to Pantone® 279 (a shade of blue) was found to be the most attractive for thrips.
• the method of killing thrips includes providing a pesticide and / or biological control agent and attracting thrips to the pesticide and / or biological control agent.
• the behaviour-modifying compound may be used to attract thrips to a pesticide or biological control agent which has been applied to a surface, e.g., the surface of a plant.
• the compound attracting the thrips directly to a pesticide and / or biological control agent suitably the compound can increase the activity of thrips so as to increase the likelihood of the thrips encountering the pesticide and / or biological control agent.
• the pesticide can be any one or more known insecticides.
• the insecticide is selected from spinosad, azadirachtin, imidacloprid, and thiacloprid.
• commercially available products such as NeemixTM and BioneemTM (which contain azadirachtin) and / or Success, SpinTor, Spinoace, Boomerang, Laser, Extinosad, conservee SC and Entrust (which contain spinosad) can be used.
• insecticides include bifenthrin (Talstar 10WP), cyfluthrin (Tempo 2E; Decathlon 20WP ), d-phenothrin (Sumithrin 2EC; PT 1400), fenpropathrin (Tame 2.4EC), fluvalinate (Mavrik 2F), permethrin (Pounce), resmethrin (SBP-1382; PT 1200), pyrethrum (Pyrenone; PT 1 100; PT 1600A), fenvalerate (Pydrin), lambda-cyhalothrin (Scimitar 10WP), acephate (PT 1300; Orthene TTO), naled (Dibrom), sulfotepp (Plantfume 103), chlorpyrifos (Dursban 50WP, Duraguard), diazinon (PT 1500R Knox Out), methiocarb (PT 1700
• the pesticide can be a biopesticide; that is, a pesticide based on a micro-organism or natural product.
• Suitable biopesticides include, for example, fungal pathogens such as Beauveria, Naturalis-O® and Naturalis-L®.
• the biological control agent can be a predatory bug or mite.
• the method may involve the use of Orius spp., Amblyseius cucumeris, Amblyseius
• the behaviour-modifying compound is provided in a composition.
• the compound may be present as a composition comprising the compound.
• the behaviour-modifying compound is provided in a thrips behaviour-modifying composition, wherein the thrips behaviour-modifying composition comprises, preferably substantially consists of, more preferably consists essentially of and most preferably consists of the behaviour-modifying compound.
• the behaviour-modifying compound can be provided as a composition comprising a pesticide.
• the pesticide can be any one or more known insecticides.
• the insecticide is selected from spinosad, azadirachtin, imidacloprid, and thiacloprid.
• commercially available products such as NeemixTM and BioneemTM (which contain azadirachtin) and / or Success, SpinTor, Spinoace, Boomerang, Laser, Extinosad, conservee SC and Entrust (which contain spinosad) can be used.
• insecticides include bifenthrin (Talstar 10WP), cyfluthrin (Tempo 2E; Decathlon 20WP ), d-phenothrin (Sumithrin 2EC; PT 1400), fenpropathrin (Tame 2.4EC), fluvalinate (Mavrik 2F), permethrin (Pounce), resmethrin (SBP-1382; PT 1200), pyrethrum (Pyrenone; PT 1 100; PT 1600A), fenvalerate (Pydrin), lambda-cyhalothrin (Scimitar 10WP), acephate (PT 1300; Orthene TTO), naled (Dibrom), sulfotepp (Plantfume 103), chlorpyrifos (Dursban 50WP, Duraguard), diazinon (PT 1500R Knox Out), methiocarb (PT 1700
• the pesticide can be a biopesticide.
• the biopesticide may be, for example, fungal pathogens such as Beauveria, Naturalis-O® and Naturalis-L®.
• the behaviour-modifying compound When formulated as a composition for killing thrips in combination with a pesticide, the behaviour-modifying compound is suitably present at a concentration of ⁇ 1 wt% based on the total weight of the composition.
• the behaviour-modifying compound is present at a concentration of ⁇ 0.5 wt%, more preferably ⁇ 0.1 wt%, more preferably ⁇ 0.05 wt%, and most preferably ⁇ 0.01 wt%.
• the behaviour-modifying compound is present in an amount of at least 10 "4 wt%.
• the composition is a liquid.
• the composition is a solid form, such as a powder.
• Embodiments of the method of the present invention may be used to monitor or control the population of thrips, particularly on members of the plant families Cucurbitaceae and Solanaceae. More generally, the methods can be used to monitor or control the population of thrips on cultivated flower crops (e.g., chrysanthemums and roses), vegetables, fruits and other crops. For example, the method may be used for monitoring or controlling the population of thrips on aubergine (eggplant, brinjal), avocado, bean, Benincasa hispida, cabbage, cantaloupe, Capsicum annum, carnation, chilli, Chinese cabbage,
• aubergine eggplant, brinjal
• avocado, bean, Benincasa hispida, cabbage, cantaloupe Capsicum annum, carnation, chilli, Chinese cabbage,
• chrysanthemum citrus, cotton, cowpea, cucumber, Cucurbita spp., Cyclamen, Ficus, hibiscus, lettuce, mango, melon, okra, onion, Orchidaceae, pea, peach, sweet pepper, plum, potato, pumpkin, rice, roses, sesame, soyabean, squash, sunflowers, tobacco, or watermelon.
• the method of monitoring or controlling thrips includes attracting thrips in a crop growing area.
• the methods of the present invention take place in an enclosed crop growing area such as a glasshouse or polytunnel.
• the methods of the present invention take place in open field conditions.
• the method of monitoring or controlling thrips suitably includes attracting thrips associated with a crop after the crop has been harvested.
• the method of monitoring or controlling thrips may include attracting thrips during crop transport or storage. This may be before or after the crop has been harvested.
• the method may be used to monitor or control thrips as a crop enters a country, such as at a port. This type of monitoring or controlling can help to prevent the spread of thrips between different geographical locations.
• the method may be used to monitor or control thrips in a quarantine area or facility.
• the behaviour-modifying compound may be used as part of a mixture of behaviour-modifying compounds.
• This mixture may include, for example, other semiochemicals such as pheromones, allomones, kairomones, attractants and repellents.
• the mixture of behaviour-modifying compounds may include a behaviour- modifying compound of Formula (1) in conjunction with one or more other thrips behaviour- modifying compounds, or in conjunction with one or more behaviour-modifying compounds that target other insects.
• the mixture may contain a behaviour-modifying compound of Formula (1) above in conjunction with neryl (S)-2-methylbutanoate (the active ingredient of "Thripline ams” by Syngenta Bioline) and / or methyl isonicotinate (the current active ingredient of "LUREM-TR” by Koppert B.V.).
• neryl (S)-2-methylbutanoate the active ingredient of "Thripline ams” by Syngenta Bioline
• / or methyl isonicotinate the current active ingredient of "LUREM-TR” by Koppert B.V.
• the use of a mixture of behaviour-modifying compounds may increase the attraction, confusion or activity of thrips compared to the use of the behaviour-modifying compound alone.
• the use of a mixture may allow other unwanted pests or beneficial predators to be attracted or repelled.
• the present invention provides the use of a behaviour-modifying compound according to any one of the formulae above in a method of monitoring thrips.
• the present invention provides the use of a behaviour-modifying compound according to any one of the formulae above in a method of controlling thrips.
• the present invention provides the use of a behaviour-modifying compound according to any one of the formulae above in a method of killing thrips.
• the present invention provides the use of a behaviour-modifying compound according to any one of the formulae above in a method of modifying the behaviour of thrips.
• the present invention provides the use of a behaviour-modifying compound according to any one of the formulae above in a method of treating a crop for thrips infestation.
• the present invention provides a method of attracting thrips to a predetermined location, the method comprising the step of providing a behaviour-modifying compound according to any one of the formulae above at the predetermined location.
• the compound is provided in a release device and the release device is located at the predetermined location.
• the present invention provides a method of monitoring thrips, the method comprising the step of providing a thrips monitoring device and a behaviour-modifying compound according to any one of the formulae above associated with the thrips monitoring device.
• the compound is provided in a release device, which is preferably attached to the thrips monitoring device.
• the thrips monitoring device is a trap, suitably a sticky trap.
• the present invention provides a method of killing thrips, the method comprising the step of providing a thrips killing device and a behaviour-modifying compound according to any one of the formulae above associated with the thrips killing device.
• the compound is provided in a release device, which is preferably attached to the thrips killing device.
• the thrips killing device is a trap, suitably a sticky trap or mass trap, for example a water trap, or other mass trapping device.
• the present invention provides a method of killing thrips, the method comprising the step of providing a pesticide or biological control agent and a behaviour- modifying compound according to any one of the formulae above associated with the pesticide or biological control agent.
• the present invention provides a method of modifying the behaviour of thrips, the method comprising the step of providing a release device comprising a behaviour- modifying compound according to any one of the formulae above.
• the present invention is also concerned with compositions for killing thrips.
• a composition for killing thrips suitably comprises a pesticide.
• the effectiveness of such a composition may be increased by including a behaviour-modifying compound according to the formulae above as an attractant, to encourage the thrips to contact the composition and hence the pesticide.
• the present invention provides a composition for killing thrips, the composition comprising a behaviour-modifying compound according to any one of the formulae above and a pesticide.
• Preferred pesticides and concentrations of the behaviour- modifying compound have been discussed above.
• the pesticide may comprise an insecticide and / or biopesticide as defined above.
• Such compositions can be used to treat a crop, for example by direct application of the composition to the crop. This may be achieved by spraying the crop with the composition.
• the present invention provides a method of treating a plant or crop comprising the step of applying a composition to the plant or crop, wherein the composition comprises an insecticide and a behaviour-modifying compound according to any one of the formulae above.
• the present invention is also concerned with release devices, thrips killing devices and thrips monitoring devices which include a behaviour-modifying compound according to any one of the formulae above.
• the present invention provides a release device comprising a behaviour-modifying compound according to any one of the formulae above.
• the release device is a lure.
• the release device may be provided in an enclosure or envelope to prevent release of the behaviour-modifying until the release device is to be used, at which point the enclosure or envelope is removed.
• the release device may be provided in an enclosure made from aluminium foil wrapped around the release device.
• the present invention provides a release device comprising a behaviour-modifying compound according to any one of the formulae above, the release device being provided in an enclosure or envelope.
• a single release device may be provided in each enclosure or envelope, or multiple release devices may be provided in each enclosure or envelope. Multiple enclosures or envelopes containing the release device may be packaged together into a pack.
• the present invention provides a pack containing a plurality of release devices, each release device or group of release device being provided in an enclosure or envelope.
• the pack may contain 2 (or more) release devices, 5 (or more) release devices, 10 (or more) release devices, 20 (or more) release devices or 25 (or more) release devices.
• the present invention provides a thrips killing device comprising a behaviour-modifying compound according to any one of the formulae above.
• the thrips killing device comprises a release device, preferably a lure.
• the present invention provides a sticky trap comprising a behaviour- modifying compound according to any one of the formulae above.
• the present invention provides a thrips killing device comprising a behaviour-modifying compound according to any one of the formulae above, the thrips killing device being provided in an enclosure or envelope.
• the present invention provides a pack containing a plurality of thrips killing devices, each thrips killing device being provided in an enclosure or envelope.
• the pack may contain 2 thrips killing devices, 5 thrips killing devices, 10 thrips killing devices, 20 thrips killing devices or 25 thrips killing devices.
• the present invention provides a thrips monitoring device comprising a behaviour-modifying compound according to any one of the formulae above.
• the thrips monitoring device comprises a release device, preferably a lure.
• the present invention provides a thrips monitoring device comprising a behaviour-modifying compound according to any one of the formulae above, the thrips monitoring device being provided in an enclosure or envelope.
• the present invention provides a pack containing a plurality of thrips monitoring devices, each thrips monitoring device being provided in an enclosure or envelope.
• the pack may contain 2 thrips monitoring devices, 5 thrips monitoring devices, 10 thrips monitoring devices, 20 thrips monitoring devices or 25 thrips monitoring devices.
• the present invention provides a method of attaching a release device comprising a behaviour-modifying compound according to any one of the formulae above to a thrips killing device or a thrips monitoring device.
• the present invention provides a method of making a release device comprising a behaviour-modifying compound according to any one of the formulae above, wherein the method includes the step of applying the compound to the release device.
• the behaviour-modifying compound is applied to the release device as a composition including a solvent, such as hexane, pentane or ether, to assist impregnation.
• the behaviour-modifying compound can also be applied undiluted.
• the method includes the step of providing an enclosure or envelope for the release device to prevent release of the behaviour-modifying compound.
• the present invention provides a method of releasing a behaviour- modifying compound according to any one of the formulae above in a glasshouse or polytunnel using a release device.
• the present invention provides a method of releasing a behaviour- modifying compound according to any one of the formulae above in an open field using a release device.
• the present invention provides a method of treating a crop for thrips infestation, wherein the method includes the step of providing at least one thrips killing device and a behaviour-modifying compound according to any one of the formulae above associated with the thrips killing device.
• the present invention provides a method of treating a crop for thrips infestation, wherein the method includes the step of providing at least one pesticide or biological control agent and a behaviour-modifying compound according to any one of the formulae above associated with the pesticide or biological control agent.
• the present invention provides a method of monitoring thrips, wherein the method includes the step of providing at least one thrips monitoring device in association with a behaviour-modifying compound according to any one of the formulae above.
• the present invention provides a behaviour-modifying compound according to Formula (1), including the preferred compounds of Formula (1) listed above.
• the present invention provides a behaviour-modifying compound according to Formula (1), including the preferred compounds of Formula (1) listed above, for use in a method of monitoring or controlling thrips.
• the compound is used in a method of monitoring or controlling Thripinae, such as T. palmi or F. intonsa.
• the compound is for use in a method of monitoring or controlling T. palmi.
• any one or more of the aspects of the present invention may be combined with any one or more of the other aspects of the present invention.
• any one or more of the features and optional features of any of the aspects may be applied to any one of the other aspects.
• the discussion herein of optional and preferred features may apply to some or all of the aspects.
• optional and preferred features relating to the nature of the behaviour-modifying compound, thrips species, crop, and behaviour-modifying compound concentrations apply to all of the aspects.
• optional and preferred features associated with a method or use may also apply to a product, in particular a composition or device, and vice versa.
• R is a C 2 -C 8 straight or branched alkenyl group and the * denotes a stereocentre.
• a method according to any one of the preceding paragraphs wherein the compound is provided in a release device. 16. A method according to paragraph 15, wherein the release device comprises a matrix and the compound is dispersed within the matrix.
• a method according to paragraph 31 wherein the substrate is in the form of a sheet.
• the trap comprises a container which in use is filled with a mixture of water and detergent.
• thrips killing device is a trap comprising a substrate and a sticky adhesive coating applied to the substrate, and the substrate or sticky adhesive coating is impregnated with the behaviour-modifying compound.
• 39. A method according to any one of the preceding paragraphs, comprising the step of providing a pesticide associated with the behaviour-modifying compound.
• the pesticide comprises an insecticide selected from spinosad, azadirachtin, imidacloprid, thiacloprid, bifenthrin, cyfluthrin , d- phenothrin, fenpropathrin, fluvalinate, permethrin, resmethrin, pyrethrum, fenvalerate, lambda-cyhalothrin, acephate, naled, sulfotepp, chlorpyrifos, diazinon, methiocarb, endosulfan, kinoprene, fenoxycarb, pyriproxyfen, oxythroquinox, abamectin, pymetrozine and pyridaben.
• insecticide selected from spinosad, azadirachtin, imidacloprid, thiacloprid, bifenthrin, cyfluthrin
• the pesticide comprises an insecticide selected from spinosad, azadirachtin, imidacloprid, thiacloprid, bifenthrin, cyfluthrin , d- phenothrin, fenpropathrin, fluvalinate, permethrin, resmethrin, pyrethrum, fenvalerate, lambda-cyhalothrin, acephate, naled, sulfotepp, chlorpyrifos, diazinon, methiocarb, endosulfan, kinoprene, fenoxycarb, pyriproxyfen, oxythroquinox, abamectin, pymetrozine and pyridaben.
• insecticide selected from spinosad, azadirachtin, imidacloprid, thiacloprid, bifenthrin, cyfluthrin
• behaviour-modifying compound is present at a concentration of ⁇ 0.1 wt% based on the total weight of the composition.
• the behaviour-modifying compound is present at a concentration of ⁇ 0.01 wt% based on the total weight of the composition.
• a method according to any one of the preceding paragraphs, wherein the method of monitoring or controlling thrips includes attracting thrips in a crop growing area.
• a method according to paragraph 50 wherein the crop comprises one or more of aubergine, avocado, bean, Benincasa hispida, cabbage, cantaloupe, Capsicum annum, carnation, chilli, Chinese cabbage, chrysanthemum, citrus, cotton, cowpea, cucumber, Cucurbita spp., Cyclamen, Ficus, hibiscus, lettuce, mango, melon, okra, onion, Orchidaceae, pea, peach, sweet pepper, plum, potato, pumpkin, rice, roses sesame, soyabean, squash, sunflowers, tobacco, or watermelon. 52. A method according to paragraph 50 or 51 , wherein the crop growing area is an enclosed crop growing area.
• the behaviour- modifying compound is present as part of a mixture of behaviour-modifying compounds.
• a composition for monitoring or controlling thrips wherein the composition comprises a pesticide and a behaviour-modifying compound of Formula (1), wherein Formula (1) is:
• R is a C 2 -C 8 straight or branched alkenyl group and the * denotes a stereocentre.
• insecticide selected from spinosad, azadirachtin, imidacloprid, thiacloprid,
• a release device comprising the behaviour-modifying compound as defined in any one of paragraphs 1 to 8, for releasing the compound in the method of any one of paragraphs 1 to 57, wherein the release device is as defined in any one of paragraphs 15 to 49.
• a release device according to paragraph 72, wherein the device is provided in an enclosure to prevent release of the behaviour-modifying compound.
• the composition applied to the release device comprises a solvent.
• 78. A method of releasing a behaviour-modifying compound as defined in any one of paragraphs 1 to 8 in a glasshouse or polytunnel using a release device according to paragraph 72.
• a method of treating a crop for thrips infestation includes the step of providing at least one thrips killing device comprising a compound as defined in any one of paragraphs 1 to 8 associated with the thrips killing device.
• a method of monitoring thrips wherein the method includes the step of providing at least one thrips monitoring device comprising a compound as defined in any one of paragraphs 1 to 8 associated with the thrips monitoring device.
• T. palmi Two alternative methods were used to collect volatile compounds emitted by T. palmi. The first of these methods was carried out on T. palmi samples transferred to FERA in York, and the second was carried out on T. palmi samples in Utsunomiya, Japan.
• the numbers of males and females entrained in this way varied from 30 to 100 per replicate and in total approximately 4 entrainments of each sex were carried out in this way. After each entrainment the SPME fibre was sealed in a clean glass tube and transferred to Keele University for GC/MS analysis.
• Swagelok T-connector into 2 separate lines. This air then entered the round bottomed flasks containing the thrips and plant material via a Drechsel head. The air exiting from each round bottomed flask then passed into a glass column containing an adsorbent polymer (ORBO 402, Tenax TA). All tubing and components within the entrainment apparatus were connected with Swagelok connectors or Teflon tubing joints and were sealed with Teflon tape (Sigma-Aldrich Company Ltd., Gillingham, United Kingdom) to eliminate leakage of air.
• adsorbent polymer ORBO 402, Tenax TA
• Air flow at the outlet of the Tenax tube was measured with a bubble flow meter and maintained at 5 ml s " by adjustment of a rotameter (GPE Ltd., Leighton Buzzard, United Kingdom) at the air inlet side of the apparatus.
• the two entrainment lines were run in parallel continuously for a period of 4 days.
• the Tenax TA columns were replaced every 24 hours with a fresh adsorbent column when fresh petals were also added to both round bottomed flasks.
• Coupled gas chromatography-mass spectrometry analyses were carried out on either a HP 5890 11+ gas chromatograph (GC) coupled to HP 5972A mass spectrometer or an Agilent 7890 GC coupled to an Agilent 5973 mass spectrometer (Agilent Technologies, Ipswich, UK). Both instruments were operated in electron impact (El) (70 eV, 180°C) mode.
• GC gas chromatograph
• El electron impact
• SPME samples from male T. palmi were analysed separately to those from female T. palmi. Analysis of SPME fibres was carried out by introducing the fibres into the HP 5890 GC via a Merlin Microseal (Thames-Restek, High-Wycombe, UK) septum-less heated injector (180°C) fitted with a SPME glass injection sleeve (0.75 mm i.d.; Supelco, UK). SPME samples were desorbed for 8 minutes before the fibre assembly was withdrawn. An initial oven
• the samples were introduced via a heated injector port (180°C).
• the GC was temperature programmed with an initial 2 minutes at 40°C, an increase of 10°C min "1 to 120°C, an increase of 6°C min "1 to 180°C, then an increase of 10°C min "1 to a final temperature of 250°C, held for 1 minute.
• the gas chromatogram of volatile compounds obtained from male T. palmi at FERA CSL showed a compound that eluted at around 18 minutes, which was completely absent from chromatograms for the females.
• the mass spectrum of the peak suggested a monoterpene ester structure similar to that of the western flower thrips aggregation pheromone neryl (S)-2- methylbutanoate but with a relative molecular weight (RM) of 236.
• T. palmi The small amounts of volatile compounds produced by T. palmi mean that such compounds can only be collected in extremely small amounts. This presents a considerable challenge when it comes to characterising the emitted compounds because the sensitivity of most characterisation techniques, including N.M.R., is too low. To solve this considerable problem, the present inventors devised an alternative approach to identify the male-specific compound with a RM of 236.
• a library of monoterpene C5 esters i.e. pentanoates, pentenoates and pentynoates was created.
• the library contains 89
• a monoterpene alcohol (1 mmol), a 5-carbon carboxylic acid (1.2 mmol), and 4- dimethylaminopyridine (DMAP) (0.05 mmol) were dissolved in dry dichloromethane (2 ml), and the solution was stirred in an ice bath.
• ⁇ /, ⁇ /'-dicylcohexylcarbodiimide (DCC) (1.2 mmol) was added portion-wise over 30 minutes, and stirring was continued for another 30 minutes with cooling and then for 3 hours at room temperature. Then the by-product in the reaction, dicyclohexylurea, was filtered off, and the precipitate was washed with petroleum spirit (boiling point 40-60°C).
• the 5-carbon carboxylic acid was synthesised from the corresponding 5- carbon alcohol.
• Jones reagent was added portion-wise over a 30 minute period to a stirred solution of the alcohol in acetone (2 ml/mmol) at 0°C until an orange colour persisted.
• the reaction mixture was then stirred for one hour.
• the progress of the reaction was monitored by TLC analysis.
• excess reagent was quenched by the addition of ethanol or methanol and then stirred for one hour.
• the solution was then concentrated under vacuum. The residue was taken up in ethyl acetate, washed with water, saturated brine, dried over anhydrous MgS0 4 , filtered and concentrated to afford the crude carboxylic acid (yield 75-80%).
• Enantiomers of lavandulol were resolved using lipase-catalysed transesterification.
• a mixture of (i)-lavandulol (2.31 g, 15 mmol), succinic anhydride (3 g, 30 mmol) and lipase (1.115 g, Fluka, 1777 U/mmol of (i)-lavandulol) was stirred in 50 ml ether at room temperature. Stirring was stopped periodically and aliquots of the supernatant solution analyzed by GC on a Cyclosil-B column (30 m x 0.25 mm; 0.25 ⁇ film) in order to monitor the progress of the transesterification.
• the reaction was terminated after 48 hours by filtration of the enzyme and dilution with 20 ml ether.
• the ethereal mixture was stirred with 1 M Na 2 C0 3 solution (60 ml) for 30 minutes.
• the basic aqueous layer was extracted with additional 20 ml of ether.
• the combined organic fractions were extracted with more 1 M Na 2 C0 3 solution (20 ml), dried over MgS0 4 and the solvent removed to give 0.68 g of the (/ ⁇ -enantiomer with an enantiomeric excess of 98% and chemical purity of 90%.
• the lavandulol was subsequently used to produce (/ ⁇ -lavandulyl 3-methyl-3-butenoate and (S)-lavandulyl 3-methyl-3-butenoate (purity 100% by TLC) in the reaction scheme described above using 3-methyl-3-butenoic acid as the 5-carbon acid.
• the crop was predominantly infested with two species of thrips: Thrips palmi (Karny) and, to a lesser extent, Frankliniella intonsa (Trybom).
• Thrips palmi Kerny
• Frankliniella intonsa Trybom
• the north-facing side of each trap was exposed and a cleaned rubber septum (diameter 6.3 mm, length 10.8 mm, International Pheromone Systems Ltd., UK) was stuck to the middle of the exposed side.
• the treatment septa received 30 ⁇ g of (/ ⁇ -lavandulyl 3-methyl-3-butenoate in 30 ⁇ hexane and the control septa received 30 ⁇ hexane.
• Pairs of treatment and control traps (treatment traps with treatment septa and control traps with control septa) with the order randomised within each pair were set out along the length of the tunnel.
• a series of four experiments was conducted over 8 days with the spacing between traps within each pair set at either 1.6 m or 4 m and the duration of the experiment lasting either 1 day or 4 days.
• New traps were set out and re-randomised for each of the four experiments. The results of the four experiments were combined. The data were log 0 (x+1) transformed and analysed by analysis of variance with trap pairs treated as blocks.

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