NZ613413A - Methods of pest control in soybean - Google Patents

Abstract

The disclosure relates a method comprising applying to a crop of soybean plants, the locus thereof, or propagation material thereof, a compound of formula (I), wherein X, R8, and p are as defined in the specification, wherein the method is for controlling and/or preventing infestation of the soybean crop by Euschistus (also known as the stink bug). The method may include combining the compound with an attractant selected from glucose, saccharide, salt, glutamate, citric acid, soybean oil peanut oil and soybean milk.

Description

S OF PEST CONTROL IN SOYBEAN The present invention and the invention ofNZ 626702, which was divided from the present application, relate to methods of pest control in n crops.

Stink bugs (Hemzptera Pentatomidae) are true bugs which can be significant pests when present in large numbers. The nymphs and adults have piercing mouthparts which most use to suck sap from plants. According to Stewart et al., Soybean Insects — Stink bugs, University of Tennessee Institute of Agriculture, W200 09-0098, stink bugs are ly the most common pest problem in soybean. Although they may feed on many parts of the plant, they typically target developing seed including the pods, meaning that injury to soybean seed is the primary problem associated with stink bug infestations.

Of the complex of sucking bugs that occur in cultivation, the brown stinkbug Euschistus heros is currently ered to be the most abundant species in northern Parana to Central Brazil (Corréa- ra & Panizzi, 1999), and is a significant problem in soybean (Schmidt et al., 2003). The bugs occur in soybeans from the vegetative stage and are harmful from the beginning ofpod formation until grain ty. They cause damage to the seed (Galileo & Heinrichs 1978a, i & Slansky Jr., 1985) and can also open the way to fungal diseases and cause physiological disorders, such as soybean leaf retention (Galileo & Heinrichs 1978, Todd & Herzog, 1980). l of stinkbugs in soybean is often vital to prevent significant economic damage.

Insecticides commonly used to control stinkbugs include pyrethroids, neonicotinoids and organophosphates, although pyrethroid insecticides are usually the method of choice for controlling stink bugs in soybean, However, there are increasing problems with insecticide resistance, particularly in brown stink bug populations and particularly to roids. ’stus heros (F.)) can also be difficult to manage using organophosphates or endosulfan (Sosa-Gomez et al., 2009). There is therefore a need for effective alternative methods of controlling stinkbugs in soybean.

Compounds that are insecticidally, acaricidally, nematicidally and/or icidally active by antagnonism of the gamma-aminobutyric acid (GABA)-gated chloride channel, and which comprise a partially saturated heterocycle that is substituted by a haloalkyl substituent and one or two optionally substituted aromatic or heteroaromatic rings, represent a new class of pesticides that are described for example in Ozoe et al. Biochemical and Biophysical Research Communications, 391 (2010) 744-749. nds from this class are broadly described in WO 85216 (EP1731512), WO 2007/123853, , W02009/002809, WO 19760, , WO 2008/128711, , , , , WO 2007/125984, WO 30651, JP 2008110971, JP2008133273, JP2009108046, W02009/022746, , , W02009/080250, W02010/020521, W02010/025998, W02010/020522, W02010/084067, W02010/086225, WOZOlO/149506 and WOZOlO/108733.

It has now surprisingly been found that particular insecticides from this new class of gamma- utyric acid (GABA)-gated chloride channel antagonists (disclosed in e.g.

(EPl731512), /002809 and WO2009/080250) are highly effective at controlling stinkbugs, and in some cases provide greater control than the current market standard. It has also surprisingly been found that these compounds t significantly higher activity against stinkbugs than structurally similar nds. These compounds ore represent an important new on for safeguarding soybean crops from stinkbugs, particularly where stink bugs are resistant to current In a first aspect the invention provides a method comprising applying to a crop of soybean plants, the locus thereof, or propagation al thereof, a compound a compound of formula I F3C O\N H l R5 0H X (R8)p (I) wherein X is P1 or P2 \ HN/\CF3 # H l / # N “\K T Y O 0 0 P1 P2 R5 is chloro, bromo, CF3 or methyl; each R8 is independently bromo, chloro, fluoro or trifluoromethyl; p is l, 2 or 3; and n the method is for controlling and/or preventing infestation of the soybean crop by Euschz'stus, preferably stus heros.

In a further aspect the invention es use of a compound of formula I for control of Euschiszfus, preferably Euschistus heros. The use may be for controlling stinkbugs (Euschistus) that are resistant to one or more other insecticides, preferably pyrethroid, neonicotinoids and organophosphates, more preferably pyrethroid insecticides.

The compounds of the invention may exist in different geometric or optical isomers or tautomeric forms. This invention covers all such isomers and tautomers and mixtures thereof in all proportions as well as isotopic forms such as deuterated compounds.The nds of the ion may contain one or more asymmetric carbon atoms, for example, at the C(#2)#3 group, and may exist as enantiomers (or as pairs of diastereoisomers) or as mixtures of such.

In one group of compounds of formula I X is P1 or P2, R5 is chloro, bromo, CF3 or methyl; each R8 is indepedently bromo, chloro, fluoro or trifluoromethyl; p is 2 or 3. Preferably X is Pl. Each R8 may take the same value.

A particularly preferred compound of formula I is a compound of formula Ix Another particularly preferred compound of formula I is a compound of a Iy F O\N F l a o 0 QN / Cl 0 The following tables illustrate specific compounds of the invention: Table 1: Table 1 es 32 compounds of formula (A) wherein G is oxygen, R7 is trifluoromethyl, R5 is , R1 is hydrogen, and cycle C and R2 have the values listed Table X below. 7 N Table X Cycle C R2 T3,5-dichloro-phenyl— (2,2,2-trifluoro-ethylcarbamoy1) -methyl X2 3,5-dichloro-phenyl- Wichloro-phenyl- (pyrid-Z-yl)-methyl- (2,2,Z-trifluoro-ethylcarbamoyl) -methyl X.4 3,4,5—trichloro-phenyl- (Pyridyl)-methyl- 3,5-dichlorofluoro-phenyl- (2,2,2-trifluoro-ethy1carbamoyl) -methyl X.6 3,5-dichlorofluoro-phenyl- (pyridyl)—methyl— Cycle C R2 .______f__ X.7 3-chlor0fluoro—pheny1- (2,2,2—trifluoro-ethylcarbamoyl) X.8 3-chlorofluoro-pheny1- (Pyrid-Z-y1)—methy1- X.9 3-fluorochloro-pheny1- (2,2,2-trifluoro-ethylcarbamoyl) —methy1 X.10 3-flu0ro—4—chloro—phenyl- (pyrid-Z-yl)-methyl— lX.11 3,4—dichlor0—phenyl- (2,2,2-trifluoro-ethylcarbamoy1) -methy1 X.12 3,4—dichloro—pheny1- (pyrid-Z-y1)—methyl- j W3,5-dichloro—4-br0m0—phenyl— (2,2,2-trifluoro-ethylcarbamoy1) —methy1 X.14 ch10r0—4-bromo~pheny1- (pyrid—Z-y1)—methyl— W3,5-dichlor0fluor0—phenyl- (2,2,2—triflu0ro-ethy1carbamoyl) 1 -methyl X. 16 3,5-dichlor0fluoro-pheny1- (pyrid—Z—y1)-methy1— X.17 3,4,5—trifluoro—pheny1— T(2,2,2—triflu0ro-ethylcarbamoyl) -methy1 X. 1 8 3 ,4,5-trifluor0-phenyl- (pyrid—Z-y1)-methyl- X. 1 9 3-chlorobr0mo-pheny1- —trifluoro-ethylcarbamoyl) -methy1 X20 3—chlorobromo—pheny1- (pyrid-Z-y1)-methy1- X21 3-chloro—5—fluoro-pheny1- (2,2,2-trifluoro-ethylcarbam0yl) -methy1 X22 3-chloroflu0r0—phenyl- -2—y1)-methy1- X23 3-chlorotrifluor0methy1-pheny1- (2,2,2-trifluoro—ethylcarbamoy1) -methy1 X24 3-chloro—5-trifluoromethy1—phenyl- (pyrid-Z—yl)—methy1- X25 3—chlor0chlorotriflu0r0methy1-phenyl- (2,2,2—triflu0ro-ethylcarbamoy1) -methy1 X26 3-chloro—4-chloro-5—trifluoromethy1—pheny1- ‘1— (pyrid-Z-yl)-methyl- X27 3,5—di-trifluoromethy1—pheny1- -trifluor0—ethylcarbam0yl) -methy1 X28 3,5-di-trifluoromethyl-phenyl- (pyrid-Z-y1)-methy1- X29 3,5-di-triflu0r0methy1-4—chloro-pheny1— (2,2,2-trifluoro—ethylcarbamoyl) 1 —methyl ‘ l Cycle C ‘ R2 l X.30 ‘ 3,5-di-trifluoromethylchloro-phenyl- ‘ (pyrid—2-yl)—methyl— X3 1 3-trifluoromethyl-phenyl- -trifluoro—ethylcarbamoyl) -methyl 3-trifluoromethyl-phenyl- (pyrid-Z-yl)-methyl- Compounds of a I include at least one chiral centre and may exist as compounds of formula 1* or compounds of formula I**.

(R8)p (R8lp (|*) 0“) Generally the compounds of formula I** are more biologically active than the tive compounds of formula 1*. The invention includes mixtures of compounds 1* and I** in any ratio e. g. in a molar ratio of 1:99 to 99: 1, e.g. 10:1 to 1:10, e.g. a substantially 50:50 molar ratio. In an enantiomerically (or epimerically) enriched mixture of formula I**, the molar proportion of compound I** compared to the total amount of both enantiomers is for e greater than 50%, e.g. at least 55, 60, 65 , 70, 75, 80, 85, 90, 95, 96, 97, 98, or at least 99%. Enantiomerically (or epimerically) enriched mixtures of a I** are preferred.

A preferred nd of the invention is a compound of formula Ix** (IX**) The compounds of the invention can be made according to the methods described in the patent applications listed above. Additional methods can be found in .

Reference to compounds of the invention also includes reference to salts and N-oxides.

The methods and uses of the invention are ably for controlling and/or preventing infestation of the soybean crop by stink bugs, including stink bugs that are resistant to other insecticides, e.g. pyrethroid insecticides. Stinkbugs that are "resistant" to a particular insecticide refers e.g. to strains of stinkbugs that are less ive to that insecticide compared to the expected ivity of the same species of stinkbug. The expected sensitivity can be measured using 6. g. a strain that has not previously been exposed to the insecticide.

Application is of the nds of the invention is to a crop of soybean plants, the locus thereof or propagation material thereof. Preferably ation is to a crop of soybean plants or the locus thereof, more preferably to a crop of soybean . Application may be before ation or when the pest is t. Application of the nds of the invention can be performed according to any of the usual modes of application, e. g. foliar, drench, soil, in furrow etc. However, control of stinkbugs is usually achieved by foliar application, which is the red mode of ation according to the invention.

The compounds of the ion may be applied in ation with an attractant. An attractant is a chemical that causes the insect to migrate s the location of application. For control of stinkbugs it can be advantageous to apply the compounds of the invention with an attractant, particularly when the application is foliar. Stinkbugs are often located near to the ground, and application of an attractant may encourage migration up the plant towards the active ingredient.

Suitable attractants e glucose, sacchrose, salt, glutamate (e.g. Aji—no-motoTM), citric acid (e.g.

Orobor TM), soybean oil, peanut oil and soybean milk. Glutamate and citric acid are of particular interest, with citric acid being preferred.

An attractant may be ed with the compound of the invention prior to ation, e. g. as a ix or tankmix, or by simultaneous application or sequential application to the plant. Suitable rates of attractants are for example 0.02kg/ha-3kg/ha.

The compounds of the invention are preferably used for pest control on soybean at 1:500 g/ha, preferably lO-70g/ha.

The compounds of the invention are suitable for use on any soybean plant, including those that have been genetically d to be resistant to active ingredients such as herbicides, or to produce biologically active compounds that control infestation by plant pests.

The compounds of the invention are preferably used for pest control on soybean at 1:500 g/ha, preferably lO-70g/ha.

The compounds of the invention are suitable for use on any soybean plant, including those that have been genetically modified to be resistant to active ingredients such as herbicides, or to e biologically active compounds that control infestation by plant pests.

In a further preferred embodiment, transgenic plants and plant cultivars obtained by genetic engineering methods, if appropriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof, are treated. ularly preferably, plants of the plant cultivars which are in each case commercially ble or in use are treated according to the invention. Plant cultivars are understood as meaning plants having novel properties ("traits") which have been obtained by conventional breeding, by mutagenesis or by recombinant DNA techniques.

These can be cultivars, bio- or genotypes. Depending on the plant species or plant cultivars, their location and growth conditions (soils, climate, vegetation period, diet), the treatment according to the invention may also result in superadditive "synergistic") effects.

Thus, for example, reduced application rates and/or a widening of the activity spectrum and/or an increase in the activity of the substances and compositions which can be used according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated maturation, higher harvest yields, higher quality and/or a higher nutritional value of the harvested ts, better storage stability and/0r processability of the harvested products are possible, which exceed the s which were actually to be ed.

The preferred transgenic plants or plant cultivars (obtained by genetic engineering) which are to be treated according to the invention include all plants which, by virtue of the genetic modification, received genetic material which imparts particularly advantageous, useful traits to these plants.

Examples of such traits are better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated maturation, higher harvest yields, higher quality and/or a higher nutritional value of the harvested ts, better storage stability and/or processability of the harvested ts.

Further and particularly emphasized examples of such traits are a better defence of the plants against animal and ial pests, such as against insects, mites, phytopathogenic fungi, bacteria and/or Viruses, and also sed tolerance of the plants to certain herbicidally active compounds.

Traits that are emphasized in particular are the increased defence of the plants against insects, ids, nematodes and slugs and snails by virtue of toxins formed in the plants, in particular those formed in the plants by the c material from Bacillus thuringiensis (for example by the genes CrylA(a), CrylA(b), CrylA(c), , CrylllA, CrleIBZ, Cry9c, CryZAb, Cry3Bb and CrylF and also combinations f) (referred to herein as "Bt plants"). Traits that are also particularly emphasized are the increased defence of the plants against fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed ns and toxins.

Traits that are furthermore particularly emphasized are the increased tolerance of the plants to n herbicidally active compounds, for example imidazolinones, sulphonylureas, glyphosate or phosphinotricin (for example the "PAT" gene). The genes which impart the desired traits in on can also be present in combination with one another in the transgenic plants.

Examples of "Bt plants" are soya bean varieties which are sold under the trade names YIELD es of herbicide-tolerant plants which may be mentioned are soya bean varieties which are sold under the trade names Roundup Ready(®) (tolerance to glyphosate), y ) ance to phosphinotricin), IMI(®) (tolerance to imidazolinones) and STS(®) (tolerance to sulphonylureas).

Herbicide—resistant plants (plants bred in a conventional manner for herbicide tolerance) which may be mentioned include the varieties sold under the name Clearfield(®) (for example maize).

Of particular interest are soybean plants carrying trains conferring resistance to 2.4D (e.g.

Enlist®), glyphosate (e.g. Roundup Ready®, Roundup Ready 2 Yield®), sulfonylurea (e.g. STS®), glufosinate (e.g. Liberty Link®, Ignite®), Dicamba (Monsanto) HPPD tolerance (e.g. utole herbicide) (Bayer ience, Syngenta). Double or triple stack in soybean plants of any of the traits described here are also of interest, including glyphosate and sulfonyl-urea tolerance (e.g. Optimum GAT®, plants stacked with STS® and Roundup Ready® or Roundup Ready 2 Yield®), dicamba and glyphosate tolerance (Monsanto). Soybean Cyst Nematode ance soybean (SCN® - Syngenta) and soybean with Aphid resistant trait (AMT® - Syngneta) are also of interest.

These statements also apply to plant cultivars having these c traits or genetic traits still to be developed, which plant cultivars will be developed and/or marketed in the future.

The compounds of the invention may be used on soybean to control, for example, Elasmopalpus lignosellus, Diloboderus s, Diabrotica speciosa, Sternechus subsignatus, Farmicidae, s ypsilon, Julus ssp., Anticarsia gemmatalz’s, Megascelz's ssp., Procornz'termes 33p, talpidae, Nezara viridula, Piezodorus Spp., ernum spp. , Neomegalotomus Spp., Ceroz‘oma trz‘furcata, Popilliajaponica, Edessa spp., Liogenysfuscus, stus heros, stalk borer, Scaptocorz’s castanea, phaga Spp., Pseudoplusia includens, Spodoptera spp. , Bemisia tabaci, Agriotes spp., preferably Difoboderus abderus, Diabrotica speciosa, Nezara viridula, Piezodorus spp., Acrosrernum spp., Cerotoma trifurcala, Papilliajaponica, Euchz'stus heros, phyllophaga Spp., Agrioz‘es spp..

The nds of the invention are preferably used on soybean to control stinkbugs, e. g.

Nezara spp. (e.g. Nezara viridula, Nezara antennata, Nezara hilare), Piezodorus spp. (e.g. Piezodorus guildinii), Acrostemum spp. Euchistus spp. (e. g. Euchistus heros, Euschistus servus), Haiyomorpha halys, Plautz'a crossota, z‘us clavatus, Rhopalus msculatus, Antestz'opsz’s orbitalus, Dichelops spp. (e. g. Dichelopsfurcalus, Dichelops melacanthus), Eurygaster spp. (e.g. Eurygaster intergriceps, Eurygaster , Oebalus Spp. (e.g. Oebalus mexicana, Oebalus poecilus, s pugnase, Scotinophara spp. (e.g. Scotinophara , Scotz‘nophara caarctata). Preferred targets include Antestiopsis orbitalus, Dichelopsfurcatus, Dichelops melacanthus, Euchistus heros, Euschistus servus, Nezara viridula, Nezara hilare, Piezodorus guildz‘m'i, Halyomorpha halys. In one embodiment the stinkbug target is Nezara viridula, Piezodorus spp.

, Acrostemum Spp, Euchistus heros. The compounds ofthe invention are particularly ive against Euschistus and in ular Euchistus heros. Euschistus and in particular Euchistus heros are the preferred s.

In order to apply a compounds of the invention as an insecticide, acaricide, nematicide or molluscicide to a pest, a locus of pest, or to a plant tible to attack by a pest, compounds of the invention is usually formulated into a composition which includes, in addition to the compound of the invention, a suitable inert diluent or carrier and, optionally, a surface active agent (SFA). SFAs are chemicals which are able to modify the properties of an interface (for e, liquid/solid, liquid/air or liquid/liquid interfaces) by lowering the interfacial tension and thereby leading to changes in other ties (for example dispersion, emulsification and wetting). It is preferred that all compositions (both solid and liquid formulations) comprise, by weight, 0.0001 to 95%, more preferably 1 to 85%, for example 5 to 60%, of a compound of the invention. The composition is generally used for the control of pests such that a compound of the invention is applied at a rate of from 0.1 g tolOkg per hectare, ably from 1 g to 6kg per hectare, more preferably from lg to 1kg per hectare.

When used in a seed dressing, a compound of the ion is used at a rate of 0.0001 g to 10g (for example 0001 g or 0.05g), preferably 0.005g to 10g, more preferably 0.005g to 4g, per kilogram of seed.

Compositions comprising a compound of the invention can be chosen from a number of formulation types, ing dustable powders (DP), soluble powders (SP), water soluble granules (SG), water dispersible granules (WG), wettable powders (WP), granules (GR) (slow or fast release), soluble concentrates (SL), oil miscible liquids (OL), ultra low volume liquids (UL), fiable concentrates (EC), dispersible concentrates (DC), emulsions (both oil in water (EW) and water in oil (EO)), micro-emulsions (ME), suspension trates (SC), aerosols, g/smoke formulations, capsule suspensions (CS) and seed treatment formulations. The formulation type chosen in any instance will depend upon the particular purpose envisaged and the physical, chemical and biological properties of the compound of the invention.

Dustable powders (DP) may be prepared by mixing a compound of the invention with one or more solid diluents (for example natural clays, kaolin, pyrophyllite, bentonite, alumina, montmorillonite, kieselguhr, chalk, diatomaceous earths, calcium phosphates, calcium and magnesium carbonates, sulfur, lime, flours, talc and other organic and inorganic solid rs) and mechanically ng the mixture to a fine powder.

Soluble powders (SP) may be prepared by mixing a compound of the invention with one or more water-soluble inorganic salts (such as sodium onate, sodium carbonate or magnesium sulfate) or one or more water—soluble organic solids (such as a polysaccharide) and, optionally, one or more wetting agents, one or more dispersing agents or a e of said agents to improve water dispersibility/solubility. The mixture is then ground to a fine powder. Similar compositions may also be granulated to form water soluble granules (SG).

Wettable powders (WP) may be prepared by mixing a compound of the invention with one or more solid diluents or carriers, one or more g agents and, preferably, one or more dispersing agents and, ally, one or more suspending agents to facilitate the dispersion in liquids. The mixture is then ground to a fine powder. Similar itions may also be granulated to form water dispersible granules (WG).

Granules (GR) may be formed either by granulating a e of a nd of the invention and one or more powdered solid diluents or carriers, or from rmed blank granules by absorbing a nd of the invention (or a solution thereof, in a suitable agent) in a porous granular material (such as pumice, lgite clays, fuller’s earth, kieselguhr, diatomaceous earths or ground corn cobs) or by adsorbing a compound of the invention (or a solution thereof, in a suitable agent) on to a hard core al (such as sands, silicates, mineral carbonates, sulfates or phosphates) and drying if necessary. Agents which are commonly used to aid absorption or adsorption e solvents (such as aliphatic and aromatic eum solvents, alcohols, ethers, ketones and ) and sticking agents (such as polyvinyl acetates, polyvinyl alcohols, dextrins, sugars and vegetable oils). One or more other additives may also be included in granules (for example an emulsifying agent, wetting agent or dispersing agent).

Dispersible Concentrates (DC) may be prepared by dissolving a compound of the invention in water or an organic solvent, such as a , alcohol or glycol ether. These solutions may contain a surface active agent (for example to improve water dilution or prevent llization in a spray tank).

Emulsifiable concentrates (BC) or -water emulsions (EW) may be prepared by dissolving a compound ofthe ion in an organic solvent (optionally containing one or more wetting agents, one or more emulsifying agents or a mixture of said agents). le organic solvents for use in ECs include aromatic hydrocarbons (such as alkylbenzenes or alkylnaphthalenes, exemplified by SOLVESSO 100, SOLVESSO 150 and SOLVESSO 200; SO is a Registered Trade Mark), ketones (such as cyclohexanone or methylcyclohexanone) and alcohols (such as benzyl alcohol, furfuryl alcohol or butanol), N-alkylpyrrolidones (such as N—methylpyrrolidone or N— yrrolidone), dimethyl amides of fatty acids (such as C8-C10 fatty acid dimethylamide) and chlorinated hydrocarbons. An EC product may spontaneously emulsify on on to water, to produce an emulsion with sufficient stability to allow spray application h appropriate equipment. ation of an EW involves obtaining a compound of the invention either as a liquid (if it is not a liquid at room temperature, it may be melted at a reasonable temperature, typically below 70°C) or in solution (by dissolving it in an appropriate solvent) and then emulsifiying the resultant liquid or on into water containing one or more SFAs, under high shear, to produce an emulsion.

Suitable solvents for use in EWs include vegetable oils, chlorinated hydrocarbons (such as chlorobenzenes), aromatic solvents (such as alkylbenzenes or alkylnaphthalenes) and other appropriate organic solvents which have a low solubility in water.

Microemulsions (ME) may be prepared by mixing water with a blend of one or more solvents with one or more SPAS, to produce spontaneously a thermodynamically stable isotropic liquid formulation. A compound of the invention is present initially in either the water or the solvent/SFA blend. Suitable ts for use in MES include those hereinbefore described for use in ECs or in EWs.

An ME may be either an oil-in-water or a water~in-oil system (which system is present may be determined by conductivity measurements) and may be suitable for mixing water-soluble and oil- soluble pesticides in the same formulation. An MB is suitable for on into water, either remaining as a microemulsion or forming a conventional oil-in-water emulsion.

Suspension concentrates (SC) may se aqueous or non-aqueous sions of finely divided insoluble solid particles of a compound of the invention. SCS may be prepared by ball or bead milling the solid compound of the invention in a le medium, optionally with one or more dispersing agents, to produce a fine particle suspension of the compound. One or more wetting agents may be included in the composition and a suspending agent may be included to reduce the rate at which the particles settle. Alternatively, a compound of the invention may be dry milled and added to water, containing agents hereinbefore described, to produce the desired end product.

Aerosol formulations comprise a compound of the invention and a suitable propellant (for example n-butane). A compound of the invention may also be dissolved or dispersed in a le medium (for example water or a water le liquid, such as n-propanol) to provide compositions for use in non—pressurized, hand-actuated spray pumps.

A compound of the invention may be mixed in the dry state with a pyrotechnic mixture to form a composition suitable for generating, in an enclosed space, a smoke containing the compound.

Capsule suspensions (CS) may be prepared in a manner r to the preparation ofEW formulations but with an additional rization stage such that an aqueous dispersion of oil ts is obtained, in which each oil t is encapsulated by a polymeric shell and contains a compound of the invention and, optionally, a carrier or diluent or. The ric shell may be produced by either an interfacial polycondensation reaction or by a coacervation procedure. The compositions may e for controlled release of the compound of the invention and they may be used for seed treatment. A compound of the invention may also be formulated in a biodegradable polymeric matrix to provide a slow, controlled release of the compound.

A composition may include one or more additives to improve the biological mance of the composition (for example by improving wetting, retention or distribution on surfaces; resistance to rain on treated surfaces; or uptake or mobility of a compound of the invention). Such additives include surface active agents, spray additives based on oils, for example certain mineral oils or natural plant oils (such as soy bean and rape seed oil), and blends of these with other bio-enhancing adjuvants (ingredients which may aid or modify the action of a compound of the invention).

A compound of the ion may also be formulated for use as a seed ent, for example as a powder composition, including a powder for dry seed treatment (DS), a water soluble powder (SS) or a water dispersible powder for slurry ent (WS), or as a liquid composition, including a flowable concentrate (FS), a solution (LS) or a capsule suspension (CS). The preparations of DS, SS, WS, FS and LS compositions are very r to those of, respectively, DP, SP, WP, SC and DC compositions described above. Compositions for treating seed may include an agent for assisting the adhesion of the composition to the seed (for example a mineral oil or a film-forming barrier).

Wetting , dispersing agents and emulsifying agents may be surface SFAs of the cationic, anionic, amphoteric or non-ionic type.

Suitable SFAs of the cationic type include nary um compounds (for example cetyltrimethyl ammonium e), imidazolines and amine salts.

Suitable anionic SFAs include alkali metals salts of fatty acids, salts of aliphatic monoesters of sulfuric acid (for example sodium lauryl sulfate), salts of sulfonated aromatic compounds (for example sodium dodecylbenzenesulfonate, calcium dodecylbenzenesulfonate, butylnaphthalene sulfonate and mixtures of sodium di-isopropyl- and tri-isopropyl-naphthalene sulfonates), ether sulfates, alcohol ether sulfates (for example sodium laurethsulfate), ether carboxylates (for e sodium laureth- 3-carboxylate), phosphate esters (products from the reaction between one or more fatty alcohols and phosphoric acid (predominately mono-esters) or phosphorus pentoxide (predominately di-esters), for example the reaction between lauryl alcohol and tetraphosphoric acid; additionally these products may be ethoxylated), sulfosuccinamates, paraffin or olefine sulfonates, taurates and lignosulfonates.

Suitable SFAs of the amphoteric type include betaines, propionates and glycinates.

Suitable SFAs of the non-ionic type include condensation ts of alkylene , such as ethylene oxide, propylene oxide, butylene oxide or mixtures thereof, with fatty alcohols (such as oleyl alcohol or cetyl alcohol) or with alkylphenols (such as octylphenol, nonylphenol or octylcresol); partial esters derived from long chain fatty acids or hexitol anhydrides; condensation ts of said partial esters with ethylene oxide; block polymers (comprising ethylene oxide and propylene oxide); alkanolamides; simple esters (for example fatty acid polyethylene glycol esters); amine oxides (for example lauryl dimethyl amine oxide); and lecithins.

Suitable ding agents include hydrophilic colloids (such as polysaccharides, polyvinylpyrrolidone or sodium ymethylcellulose) and swelling clays (such as bentonite or attapulgite).

A compound of the invention may be applied by any of the known means of applying pesticidal compounds. For example, it may be applied, formulated or unfonnulated, to the pests or to a locus of the pests (such as a habitat of the pests, or a growing plant liable to infestation by the pests) or to any part of the plant, including the e, stems, branches or roots, to the seed before it is planted or to other media in which plants are growing or are to be planted (such as soil surrounding the roots, the soil generally, paddy water or hydroponic e systems), directly or it may be sprayed on, dusted on, applied by dipping, applied as a cream or paste ation, applied as a vapor or applied through distribution or incorporation of a composition (such as a ar composition or a composition packed in a soluble bag) in soil or an aqueous environment.

A compound of the invention may also be injected into plants or sprayed onto vegetation using electrodynamic spraying techniques or other low volume s, or applied by land or aerial irrigation systems.

Compositions for use as aqueous preparations (aqueous ons or dispersions) are lly supplied in the form of a concentrate containing a high proportion of the active ingredient, the concentrate being added to water before use. These concentrates, which may e DCs, SCs, ECs, EWs, MES, SGs, SPs, WPs, WGs and CSs, are often required to withstand storage for prolonged periods and, after such storage, to be capable of addition to water to form aqueous preparations which remain homogeneous for a sufficient time to enable them to be d by conventional spray equipment. Such aqueous preparations may contain varying amounts of a nd of the invention (for example 0.0001 to 10%, by ) depending upon the e for which they are to be used.

A nd of the invention may be used in mixtures with fertilizers (for example nitrogen—, potassium- or phosphorus-containing fertilizers). le formulation types include granules of fertilizer. The mixtures preferably contain up to 25% by weight of the compound of the invention.

The invention ore also es a fertilizer composition comprising a fertilizer and a compound of the invention.

The compositions of this invention may contain other compounds having biological activity, for example micronutrients or compounds having fungicidal activity or which possess plant growth regulating, idal, insecticidal, nematicidal or acaricidal activity.

The compound ofthe invention may be the sole active ingredient of the ition or it may be admixed with one or more additional active ingredients such as a pesticide, fungicide, synergist, herbicide or plant growth tor where appropriate. An additional active ingredient may: provide a composition having a r um of activity or increased persistence at a locus; synergize the ty or ment the activity (for example by increasing the speed of effect or overcoming repellency) of the compound of the invention; or help to overcome or prevent the development of resistance to individual components. The particular additional active ient will depend upon the intended utility of the composition. Examples of suitable pesticides include the following: a) a pyrethroid including those selected from the group consisting of permethrin, cypermethrin, fenvalerate, esfenvalerate, deltamethrin, cyhalothrin, lambda—cyhalothrin, gamma- cyhalothrin, bifenthrin, fenpropathrin, cyfluthrin (including beta cyfluthrin), tefluthrin, ethofenprox, natural rin, tetramethrin, S-bioallethrin, fenfluthrin, prallethrin and -benzyl-3 -furylmethyl—(E)-(1R,3 S)-2,2-dimethyl- xothiolanylidenemethyl)cyclopropane ylate; b) an organophosphate including those selected from the group consisting of sulprofos, acephate, methyl parathion, azinphos-methyl, demeton—s-methyl, heptenophos, thiometon, fenamiphos, monocrotophos, profenofos, triazophos, methamidophos, dimethoate, phosphamidon, ion, chlorpyrifos, phosalone, terbufos, fensulfothion, fonofos, phorate, phoxim, pirimiphos-methyl, pirimiphos—ethyl, fenitrothion, fosthiazate and diazinon; c) a carbamate including those selected from the group consisting of pirimicarb, triazamate, cloethocarb, carbofuran, furathiocarb, ethiofencarb, aldicarb, thiofurox, carbosulfan, bendiocarb, fenobucarb, propoxur, methomyl, thiodicarb and oxamyl; d) a benzoyl urea including those ed from the group consisting of diflubenzuron, triflumuron, hexaflumuron, flufenoxuron, lufenuron and chlorfluazuron; e) an organic tin compound selected from the group consisting of cyhexatin, fenbutatin oxide and azocyclotin; i) a le ing those selected from the group consisting of npyrad and fenpyroximate; g) a macrolide including those selected from the group consisting of abamectin, emamectin (e.g. emamectin benzoate), ivermectin, milbemycin, spinosad, azadirachtin and spinetoram; h) an organochlorine compound including those selected from the group ting of endosulfan (in particular alpha-endosulfan), benzene loride, DDT, chlordane and dieldn'n; i) an amidine including those selected from the group consisting of chlordimeform and amitraz; j) a fumigant agent ing those selected from the group consisting of chloropicrin, dichloropropane, methyl bromide and metam; k) a neonicotinoid compound including those ed from the group consisting of imidacloprid, thiacloprid, acetamiprid, nitenpyram, dinotefuran, thiamethoxam, clothianidin, nithiazine and flonicamid; 1) a diacylhydrazine including those selected from the group consisting of tebufenozide, chromafenozide and methoxyfenozide; m) a diphenyl ether including those selected from the group consisting of diofenolan and pyriproxyfen; n) indoxacarb; o) enapyr; p) pymetrozine; q) a tetramic acid compound including those selected from the group consisting of spirotetramat and spirodiclofen, or a tetronic acid compound including spiromesifen; r) a diamide including those selected from the group consisting of flubendiamide, chlorantraniliprole ypyr®) and cyantraniliprole; s) sulfoxaflor; t) metaflumizone; u) fipronil and ole; v) pyrifluqinazon; W) buprofezin; x) diafenthiuron; y) 4—[(6-Chloro-pyridin~3~ylmethyl)~(2,2-difluoro-ethyl)-amino]—5H-furan—2-one (DE 102006015467); 2) flupyradifurone. aa) CAS: 9159727 (WO 2006129714; W02011/147953; W02011/147952) ab) CAS: 269148 (WO 2007020986) In addition to the major al classes of pesticide listed above, other pesticides having particular targets may be employed in the composition, if appropriate for the intended utility of the composition. For instance, selective insecticides for particular crops, for example stemborer specific insecticides (such as cartap) or hopper specific insecticides (such as buprofezin) for use in rice may be employed. Alternatively insecticides or acaricides specific for ular insect species/stages may also be included in the compositions (for example idal ovo-larvicides, such as clofentezine, flubenzimine, hexythiazox or ifon; acaricidal cides, such as dicofol or propargite; acaricides, such as bromopropylate or chlorobenzilate; or growth regulators, such as hydramethylnon, cyrornazine, methoprene, chlorfluazuron or diflubenzuron).

Examples of fungicidal compounds which may be included in the composition of the ion are (E)-N—methyl[2—(2,5-dimethylphenoxymethyl)phenyl]~2—methoxy-iminoacetamide (SSF-129), 4-bromo-2—cyano-N,N—dimethyltrifluoromethylbenzimidazole-l -sulfonamide, 0t-[N—(3—chloro-2,6— —xylyl)—2—methoxyacetamido]—y—butyrolactone, 4—chloro—2-cyano-N,N-dimethyl—5-p—tolylimidazole-l - amide (lKF-916, cyamidazosulfamid), 3—5-dichloro—N-(3 -chloro-l —ethyl-1—methy1oxopropyl)- 4—methylbenzamide (RH—728 1 , zoxamide), N—allyl-4,5,—dimethyl~2—trimethylsilylthiophene-3— carboxamide (MON65500), N-(l -cyano-l ,2-dimethylpropyl)—2—(2,4—dichlorophenoxy)propionamide (AC3 82042), N-(Z-methoxy—S-pyridyl)—cyclopropane amide, acibenzolar (CGA245704), alanycarb, aldimorph, ine, azaconazole, azoxystrobin, benalaxyl, benomyl, biloxazol, bitertanol, blasticidin S, bromuconazole, bupirimate, captafol, , carbendazim, carbendazim chlorhydrate, carboxin, carpropamid, carvone, CGA41396, CGA41397, chinomethionate, chlorothalonil, chlorozolinate, clozylacon, copper containing compounds such as copper oxychloride, copper oxyquinolate, copper sulfate, copper tallate and Bordeaux mixture, cymoxanil, cyproconazole, cyprodinil, debacarb, dipyridy1 disulfide ioxide, dichlofluanid, diclomezine, dicloran, diethofencarb, difenoconazole, difenzoquat, torim, 0,0-di-iso-propy1—S—benzyl thiophosphate, dimefluazole, dimetconazole, dimethomorph, dimethirimol, diniconazole, dinocap, dithianon, dodecyl dimethyl ammonium chloride, dodemorph, dodine, doguadine, edifenphos, onazole, ethirimol, ethyl-(Z)-N—benzyl-N—([methyl(methyl-thioethylideneaminooxycarbonyl)amino]thio)—B-alaninate, etridiazole, famoxadone, done (RPA407213), fenarirnol, fenbuconazole, fenfuram, fenhexamid (KBR2738), fenpiclonil, fenpropidin, pimorph, fentin acetate, fentin hydroxide, ferbam, ferimzone, fluazinam, fludioxonil, flumetover, fluoroimide, fluquinconazole, flusilazole, flutolanil, flutriafol, , fuberidazole, furalaxyl, furametpyr, guazatine, hexaconazole, hydroxyisoxazole, hymexazole, imazalil, imibenconazole, iminoctadine, iminoctadine triacetate, ipconazole, iprobenfos, iprodione, iprovalicarb (SZXO722), isopropanyl butyl carbamate, isoprothiolane, kasugamycin, kresoxim-methyl, LY186054, LY211795, LY248908, mancozeb, maneb, mefenoxam, mepanipyrim, mepronil, metalaxyl, metconazole, metiram, metiram-zinc, metominostrobin, myclobutanil, neoasozin, nickel dimethyldithiocarbamate, hal-z‘sopropyl, ol, ofurace, organomercury compounds, oxadixyl, furon, oxolinic acid, oxpoconazole, oxycarboxin, pefurazoate, penconazole, pencycuron, phenazin oxide, yl-Al, phosphorus acids, phthalide, picoxystrobin (ZAl963), poly- oxin D, polyram, azole, prochloraz, idone, ocarb, propiconazole, propineb, propionic acid, pyrazophos, pyrifenox, pyrimethanil, pyroquilon, pyroxyfur, pyrrolnitrin, quaternary ammonium nds, quinomethionate, quinoxyfen, quintozene, sipconazole (F-155), sodium pentachlorophenate, spiroxamine, streptomycin, sulfur, tebuconazole, tecloftalam, tecnazene, onazole, thiabendazole, thifluzamid, 2-(thiocyanomethylthio)benzothiazole, thiophanate-methyl, thiram, timibenconazole, tolclofos—methyl, tolylfluanid, triadimefon, triadimenol, triazbutil, triazoxide, lazole, tridemorph, trifloxystrobin (CGA279202), ine, triflumizole, triticonazole, validamycin A, vapam, vinclozolin, zineb, ziram; N—[9-(dichloromethylene)—l,2,3,4—tetrahydro-l ,4- methanonaphthalen-S-yl] ~3 -(difluoromethyl)—l -methyl-1H—pyrazolecarboxamide [1072957-71 - l ], l-methyl-3 -difluoromethyl—lH-pyrazolecarboxylic acid (2-dichloromethylene—3-ethyl-l -methyl- 4-yl)-amide, and yl-3 -difluoromethyl—4H—pyrazole—4—carboxylic acid [2-(2,4-dichlorophenyl )methoxy—l -methyl-ethyl]-amide.

Preferred additional idally active ients are those selected from neonicotinoids, roids, strobilurins, triazoles and carboxamides (SDHI inhibitors). Pyrethroids are of interest of which lambda—cyhalothrin is of particular interest. Combinations of compounds of the invention, particularly compounds from Table A, and particularly when X is P3, P4 or P5 and pyrethroids, in parrticular lambda-cyhalothrin, exhibit synergistic l of stinkbugs (according to the Colby formula), in particular Euschistus, e.g. Euschistus heros.

In a further aspect of the invention there is provided a method comprising applying to a crop of soybean plants, the locus thereof, or propagation material thereof, a combination of a compound a compound of the invention and lambda cyhalothrin in a synergistically effective amount, wherein the method is for control and/0r prevention of stinkbugs, ably Euschz'stus, e. g. Euschiszus heros. In one embodiment the compound is a compound of formula I. In another embodiment the compound is a compound of formula II. In another embodiment the compound is a compound of formula III. In r ment the compound is a compound of formula IV. ably the compound is a compound from Table A.

The compounds of the invention may be mixed with soil, peat or other rooting media for the protection of plants against seed—borne, ome or foliar fungal diseases. es of suitable synergists for use in the compositions include piperonyl butoxide, sesamex, safroxan and l ole.

Suitable herbicides and plant-growth regulators for inclusion in the compositions will depend upon the intended target and the effect required.

An example of a rice selective herbicide which may be included is propanil. An example of a plant growth regulator for use in cotton is PIXTM.

Some mixtures may comprise active ingredients which have significantly different physical, chemical or biological properties such that they do not easily lend themselves to the same conventional formulation type. In these circumstances other formulation types may be prepared. For example, where one active ingredient is a water insoluble solid and the other a water insoluble liquid, it may heless be possible to disperse each active ingredient in the same continuous aqueous phase by dispersing the solid active ingredient as a suspension (using a preparation analogous to that 'of an SC) but dispersing the liquid active ingredient as an emulsion (using a preparation analogous to that of an EW). The resultant composition is a suspoemulsion (SE) ation.

Unless otherwise stated the weight ratio of the compound of I, II, III or IV with an additional active ingredient may generally be between 1000 : 1 and 1 : 1000. In other embodiments that weight ratio ofA to B may be between 500 : 1 to l : 500, for example between 100 : 1 to 1 : 100, for example between 1 :50 to 50 : 1, for example 1 :20 to 20 : 1, for example 1:10 to 10:1, for example 1:5 to 5:1, for example 1:1. itions of the ion include those prepared by premixing prior to application, e.g. as a readymix or tankmix, or by simultaneous application or sequential application to the plant.

The invention will now be illustrated by the following non-limiting Examples. All citations are incorporated by reference.

Figures Figure 1 shows the s of a field trial to investigate control of Euschistus heros on soybeans with the nd of formula Ix (racemic mixtures of enantiomers) . The X axis indicates grams of active ingredient per hectare of (a) beta-cyfluthrin + imidacloprid, (b) thiamethoxam + lambda cyhalothn'n, (c) formula Ix at 35 g/ha, (d) formula Ix at 53 g/ha. The Y axis indicates % control. Bars 1-5 show control after 1, 3, 5, 8 and 15 days after application respectively. Experimental details are indicated in Example 1.

Figure 2 shows the results of a field trial to investigate control of Euschz’stus heros on soybeans with the compound of formula Ix (racemic mixtures of enantiomers). The X axis indicates grams of active ient per hectare of (a) beta—cyfluthrin + imidacloprid, (b) thiamethoxam + lambda cyhalothrin, (c) formula Ix at 35 g/ha, (d) formula Ix at 53 g/ha. The Y axis indicates % l. Bars 1- 4 show control after 2, 5, 12 and 16 days after application respectively. mental details are ted in Example 2.

Figure 3 shows the results of a field trial to investigate control of stus heros on soybeans with the compound of formula Ix (racemic mixtures of enantiomers) and formula Iy (racemix mixture of enantiomers). The X axis indicates grams of active ingredient per hectare of (a) thiamethoxam + lambda cyhalothrin, (b) methamidophos, (c) formula Iy at 60 g/ha, (d) formula Iy at 120 g/ha, (e) formula Ix at 60 g/ha, (f) formula Ix at 120 g/ha. The Y axis indicates % control. Bars 1-5 show control after 2, 5, 7, 10 and 13 days after ation tively. Experimental details are indicated in Example 3.

Examples Example 1 Field trial: control of Euschistus heros on soybeans. Application was Foliar ation using a rayer. The spray volume was 200 l/ha. Each plot size was 60m2. The soybean was at growth stage bbch 72. The compound of formula Ix was applied as an EC formulation. The beta-cyfluthrin + loprid (9.4 g/ha and 75 g/ha respectively) / thiamethoxam + lambda-cyhalothrin (21.2 g/ha and 28.2 g/ha respectively) were applied as suspension concentrate formulations. The results (% control of adults) are shown in Figure l and represent the average of 3 replicates.

Field trial: control of Euschistus heros on soybeans. Application was Foliar application using a boomsprayer. The spray volume was 200 l/ha. Each plot size was 108ml. The soybean was at growth stage bbch 72. The compound of formula Ix was applied as an EC formulation. The beta-cyfluthrin + imidacloprid (9.4 g/ha and 75 g/ha respectively) / thiamethoxam + -cyhalothrin (21.2 g/ha and 28.2 g/ha respectively) were applied as suspension concentrate formulations. The results (% control of ) are shown in Figure 2 and represent the average of 3 ates.

Example 3 Field trial: control of Euschz’stus heros on soybeans. ation was Foliar application using a boomsprayer. The spray volume was 200 l/ha. Each plot size was 108mg. The soybean was at growth stage bbch 75. The compounds of formula IX and ly were applied as an EC formulation. The thiamethoxam + lambda—cyhalothrin (21.2 g/ha and 28.2 g/ha respectively) was applied as a suspension concentrate formulation. The methamidophos was applied as a soluble concentrate formulation. The results (% control of adults) are shown in Figure 3 and represent the e of 3 ates.

Example 4 Euschistus heros (Neotropical brown stink bug) (contact/feeding activity) 2 week old soybean plants are sprayed in a turn table spray chamber with the diluted spray solutions.

After drying, 2 n seeds are added and plants are infested with 10 N-2 nymphs of the neotropical brown stink bug Eusckistus heros in plastic test boxes. Boxes are incubated in a climate chamber at °C and 60 % RH. Evaluation is done 5 days after infestation on mortality and growth effects. The results are shown in Table E1 below. The data is an average of two replicates.

The results show that the compounds of the invention are significantly more active against stinkbugs than structurally similar compounds, ularly at low rates of application.

Table E1 [—Rate / ppm Compound 1 Compound 2 Compound 3 Compound 4 Compound 5 (reference rative (comparative (comparative example) example) example) example) Compounds 1-5 are compounds from W02005/085216 (EPl731512) and W02009/002809.

References Corréa-Perreira, B. S.; Panizzi, A. R., Percevejos da soja e seu manejo, Londrina: Embrapa-CNPSo, 1999, 45 (Circular Te’cnica, 24).

Galileo, M.H.M., Heinrichs E.A., ao foliar em plantas de soja (glycine max (1.) merrill) resultantes da acao de Piezodorus guildz'nz'i (Westwood, 1837) (Hemiptera pentatomidae), em diferentes niveis e épocas de infestacao. An. Soc. l. Brasil, 1978, 7, 85-98.

Panizzi, A. R., Slansky junior, F. Review of phytophagous pentatomids (Hemiptera omidae) associated with soybean in the Americas, Florida logist, Gainesville, 1985, 68(1), 184-214.

Schmidt, F. G. V., Fires, C. S. S., Sujii, E. R,., Borges, M,., Pantaleao, D. C., a, A. L., Azevedo, C. R., Comportamento e captura das fémeas de Euschistus heros em armadilhas s com feromonio sexual, 2003, Comunicado Te’cnico 93. Brasilia, DF. omez, D.R., Silva, J. Da., Lopes, I. O. N., Corso, 1., Almeida, A.M. R. Almeida, moraes, g. c.p.m.; baur, m. insecticide susceptibility of Euschz‘stus heros (Heteroptera pentatomidae) in Brazil, Journal of Economic Entomology, 2009, 102(3), 1209-1216.

Todd, J. W., Herzog, D. 0, Sampling phytophagous pentatomz'dae on soybean. in: Kogan, zog, D. C. (ed.). Sampling methods in soybean entomology, New York: Springer, 1980, 438-478.

Claims (8)

What is claimed

1. A method sing applying to a crop of soybean plants, the locus thereof, or propagation material thereof, a compound of formula I F3C O‘N H l R5 (R8)p (I) wherein X is P1 or P2 \ HNACFB H l H #\n/N N/ #\H/N\/§O 0 0 P1 P2 R5 is chloro, bromo, CF3 or ; each R8 is independently bromo, chloro, fluoro or trifluoromethyl; p is l, 2 or 3; and wherein the method is for controlling and/or preventing infestation of the soybean crop by Euschistus.

2. Use of a compound of a I as defined in claim 1 for control ofEuschistus.

3. A method or use according to claim 1 or claim 2, wherein the compound of formula I is a compound of formula Ix

4. A method or use according to any one of claims 1 to 3, n Euschiszus is Euschistus heros.

5. A method or use according to any one of claims 1 to 4, wherein the compound of formula I or formula II is applied in combination with one or more additional active ients selected from neonicotinoids, pyrethroids, strobilurins, triazoles and amides.

6. A method or use according to any one of claims 1 to 5, wherein the compound is applied to the crop by foliar application.

7. A method or use according to any one of claims 1 to 6, wherein the compound of formula I is applied in combination with an attractant selected from glucose, saccharose, salt, glutamate, citric acid, soybean oil, peanut oil and soybean milk.

8. A method according to claim 1, substantially as herein described with reference to any one of the Examples and/or