NZ613413B2 - 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. 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 ion ofNZ 626702, which was d 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 lture, W200 09-0098, stink bugs are probably the most common pest problem in soybean. Although they may feed on many parts of the plant, they typically target ping 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- Ferreira & Panizzi, 1999), and is a significant m in soybean (Schmidt et al., 2003). The bugs occur in soybeans from the vegetative stage and are l from the beginning ofpod formation until grain maturity. They cause damage to the seed (Galileo & Heinrichs 1978a, Panizzi & 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 & , 1980).

Control 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 pyrethroids. Euschz’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 tuted ic 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 (EP1731512), WO 2007/123853, , W02009/002809, , , 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 de channel antagonists (disclosed in e.g.

(EPl731512), W02009/002809 and WO2009/080250) are highly effective at controlling stinkbugs, and in some cases provide greater control than the current market standard. It has also singly been found that these compounds exhibit significantly higher activity against stinkbugs than structurally r compounds. These compounds therefore represent an important new solution for safeguarding soybean crops from stinkbugs, particularly where stink bugs are resistant to current methods.

In a first aspect the invention provides a method comprising applying to a crop of soybean plants, the locus thereof, or propagation material thereof, a compound a compound of a 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 oromethyl; 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 Euschistus heros.

In a further aspect the invention provides 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, otinoids and organophosphates, more preferably pyrethroid insecticides.

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

In one group of nds 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 nd of formula I is a compound of formula Ix Another particularly preferred compound of formula I is a compound of formula Iy F O\N F l a o 0 QN / Cl 0 The ing tables illustrate c compounds of the invention: Table 1: Table 1 provides 32 nds of formula (A) wherein G is oxygen, R7 is trifluoromethyl, R5 is methyl, 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) -methy1 X.8 3-chlorofluoro-pheny1- (Pyrid-Z-y1)—methy1- X.9 3-fluorochloro-pheny1- -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) 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 3,5~dich10r0—4-bromo~pheny1- (pyrid—Z-y1)—methyl— W3,5-dichlor0fluor0—phenyl- (2,2,2—triflu0ro-ethy1carbamoyl) 1 -methyl X. 16 3,5-dichlor0fluoro-pheny1- —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- (2,2,2—trifluoro-ethylcarbamoyl) -methy1 X20 robromo—pheny1- (pyrid-Z-y1)-methy1- X21 3-chloro—5—fluoro-pheny1- (2,2,2-trifluoro-ethylcarbam0yl) -methy1 X22 3-chloroflu0r0—phenyl- (pyrid-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- (2,2,2-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- (2,2,2-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 respective 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 example 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 es of formula I** are preferred.

A preferred compound 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. onal methods can be found in .

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

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

Application is of the compounds of the invention is to a crop of soybean plants, the locus f or propagation al thereof. Preferably application is to a crop of soybean plants or the locus f, more preferably to a crop of soybean plants. Application may be before infestation or when the pest is present. Application of the compounds of the invention can be performed ing 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 preferred mode of application according to the invention.

The compounds of the invention may be applied in combination with an attractant. An attractant is a chemical that causes the insect to migrate towards the location of application. For l of stinkbugs it can be advantageous to apply the compounds of the ion 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 include glucose, sacchrose, salt, glutamate (e.g. Aji—no-motoTM), citric acid (e.g.

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

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

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

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

The nds of the ion 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 produce 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. Particularly preferably, plants of the plant cultivars which are in each case commercially available 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 inant DNA ques.

These can be ars, 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 ion may also result in superadditive "synergistic") effects.

Thus, for example, d 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 products, better storage stability and/0r processability of the harvested ts are possible, which exceed the effects which were actually to be expected.

The preferred transgenic plants or plant cultivars ned by c 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, rated maturation, higher harvest yields, higher quality and/or a higher nutritional value of the harvested products, better storage ity and/or processability of the harvested products.

Further and ularly emphasized examples of such traits are a better defence of the plants against animal and microbial 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, arachnids, nematodes and slugs and snails by virtue of toxins formed in the plants, in ular those formed in the plants by the c material from Bacillus thuringiensis (for example by the genes CrylA(a), CrylA(b), CrylA(c), CryllA, A, CrleIBZ, Cry9c, CryZAb, Cry3Bb and CrylF and also ations thereof) (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, ors and resistance genes and correspondingly expressed proteins and toxins.

Traits that are furthermore particularly emphasized are the increased tolerance of the plants to certain herbicidally active compounds, for example imidazolinones, sulphonylureas, sate or phosphinotricin (for example the "PAT" gene). The genes which impart the desired traits in question 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 GARD(®) Examples of herbicide-tolerant plants which may be mentioned are soya bean varieties which are sold under the trade names Roundup Ready(®) (tolerance to glyphosate), Liberty ) (tolerance to phosphinotricin), IMI(®) (tolerance to imidazolinones) and STS(®) (tolerance to sulphonylureas).

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

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

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

These ents also apply to plant cultivars having these genetic 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, derus abderus, Diabrotica speciosa, Sternechus subsignatus, Farmicidae, Agrotis ypsilon, Julus ssp., Anticarsia gemmatalz’s, Megascelz's ssp., Procornz'termes 33p, Gryllotalpidae, Nezara viridula, Piezodorus Spp., Acrosternum spp. , Neomegalotomus Spp., oma trz‘furcata, Popilliajaponica, Edessa spp., Liogenysfuscus, Euchz’stus heros, stalk borer, Scaptocorz’s castanea, phyilophaga Spp., plusia includens, Spodoptera spp. , Bemisia tabaci, Agriotes spp., preferably derus abderus, Diabrotica speciosa, Nezara viridula, Piezodorus spp., Acrosrernum spp., Cerotoma trifurcala, Papilliajaponica, Euchz'stus heros, phyllophaga Spp., Agrioz‘es spp..

The compounds of the invention are preferably used on soybean to l stinkbugs, e. g.

Nezara spp. (e.g. Nezara la, 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, Riptorz‘us clavatus, Rhopalus msculatus, Antestz'opsz’s orbitalus, Dichelops spp. (e. g. Dichelopsfurcalus, Dichelops nthus), Eurygaster spp. (e.g. Eurygaster intergriceps, Eurygaster maura), Oebalus Spp. (e.g. Oebalus mexicana, Oebalus poecilus, Oebalus pugnase, Scotinophara spp. (e.g. Scotinophara Zurida, Scotz‘nophara caarctata). Preferred targets include iopsis orbitalus, Dichelopsfurcatus, Dichelops melacanthus, Euchistus heros, Euschistus servus, Nezara viridula, Nezara hilare, Piezodorus guildz‘m'i, Halyomorpha halys. In one ment the stinkbug target is Nezara viridula, Piezodorus spp. , emum Spp, Euchistus heros. The compounds ofthe invention are particularly ive t Euschistus and in particular Euchistus heros. Euschistus and in particular Euchistus heros are the preferred targets.

In order to apply a compounds of the invention as an icide, acaricide, nematicide or molluscicide to a pest, a locus of pest, or to a plant susceptible to attack by a pest, compounds of the invention is usually formulated into a composition which es, 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 example, liquid/solid, liquid/air or liquid/liquid interfaces) by lowering the interfacial tension and thereby leading to changes in other properties (for example dispersion, fication and g). 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 nd 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 e.

When used in a seed dressing, a compound of the invention 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. itions comprising a compound of the invention can be chosen from a number of formulation types, including dustable powders (DP), soluble powders (SP), water soluble es (SG), water dispersible granules (WG), wettable s (WP), granules (GR) (slow or fast e), soluble concentrates (SL), oil miscible liquids (OL), ultra low volume s (UL), emulsifiable concentrates (EC), dispersible concentrates (DC), emulsions (both oil in water (EW) and water in oil (EO)), micro-emulsions (ME), sion concentrates (SC), aerosols, fogging/smoke formulations, capsule suspensions (CS) and seed treatment formulations. The formulation type chosen in any instance will depend upon the particular purpose ged 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 ts (for example natural clays, kaolin, pyrophyllite, bentonite, a, montmorillonite, kieselguhr, chalk, diatomaceous earths, calcium phosphates, calcium and ium carbonates, sulfur, lime, flours, talc and other organic and inorganic solid carriers) and mechanically grinding the mixture to a fine powder.

Soluble s (SP) may be prepared by mixing a compound of the invention with one or more water-soluble inorganic salts (such as sodium bicarbonate, sodium carbonate or magnesium e) 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 mixture 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 wetting agents and, preferably, one or more dispersing agents and, optionally, one or more suspending agents to facilitate the dispersion in liquids. The mixture is then ground to a fine powder. r compositions may also be granulated to form water dispersible granules (WG).

Granules (GR) may be formed either by granulating a mixture of a compound of the invention and one or more powdered solid diluents or carriers, or from pre-formed blank granules by absorbing a compound of the invention (or a solution thereof, in a suitable agent) in a porous granular material (such as pumice, attapulgite clays, fuller’s earth, kieselguhr, diatomaceous earths or ground corn cobs) or by adsorbing a compound of the invention (or a solution f, in a suitable agent) on to a hard core material (such as sands, silicates, mineral carbonates, sulfates or phosphates) and drying if ary. Agents which are commonly used to aid tion or adsorption include solvents (such as aliphatic and aromatic petroleum solvents, alcohols, ethers, ketones and esters) 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). sible Concentrates (DC) may be ed by dissolving a compound of the invention in water or an organic solvent, such as a ketone, alcohol or glycol ether. These solutions may contain a e active agent (for example to improve water on or prevent crystallization in a spray tank).

Emulsifiable concentrates (BC) or oil—in-water emulsions (EW) may be prepared by dissolving a compound ofthe invention in an organic solvent (optionally containing one or more wetting agents, one or more emulsifying agents or a mixture of said agents). Suitable organic solvents for use in ECs e aromatic hydrocarbons (such as alkylbenzenes or alkylnaphthalenes, ified by SOLVESSO 100, SOLVESSO 150 and SOLVESSO 200; SOLVESSO 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— octylpyrrolidone), dimethyl amides of fatty acids (such as C8-C10 fatty acid dimethylamide) and nated hydrocarbons. An EC product may spontaneously emulsify on addition to water, to produce an emulsion with sufficient stability to allow spray application through appropriate equipment. Preparation 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 able temperature, typically below 70°C) or in on (by dissolving it in an appropriate solvent) and then fiying the ant liquid or solution into water containing one or more SFAs, under high shear, to produce an on.

Suitable solvents for use in EWs include vegetable oils, chlorinated hydrocarbons (such as chlorobenzenes), aromatic ts (such as alkylbenzenes or alkylnaphthalenes) and other appropriate organic solvents which have a low lity 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 lly in either the water or the solvent/SFA blend. Suitable solvents 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 ation. An MB is suitable for dilution into water, either remaining as a microemulsion or forming a conventional oil-in-water emulsion.

Suspension concentrates (SC) may comprise aqueous or non-aqueous suspensions 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 suitable medium, optionally with one or more dispersing agents, to produce a fine particle sion 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 d end product. l formulations comprise a nd of the ion and a le propellant (for example n-butane). A compound of the invention may also be dissolved or dispersed in a suitable medium (for example water or a water miscible 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 similar to the preparation ofEW formulations but with an additional polymerization stage such that an aqueous dispersion of oil droplets is obtained, in which each oil droplet is encapsulated by a polymeric shell and contains a nd of the invention and, optionally, a carrier or diluent therefor. The polymeric shell may be produced by either an acial polycondensation reaction or by a coacervation procedure. The compositions may e for lled release of the nd of the invention and they may be used for seed treatment. A compound of the invention may also be formulated in a radable ric matrix to provide a slow, controlled release of the compound.

A composition may include one or more additives to improve the biological performance of the ition (for example by improving wetting, retention or distribution on es; 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 dients which may aid or modify the action of a compound of the invention).

A compound of the invention may also be formulated for use as a seed treatment, 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 treatment (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 similar to those of, respectively, DP, SP, WP, SC and DC compositions bed above. itions for treating seed may include an agent for assisting the adhesion of the ition to the seed (for example a mineral oil or a film-forming barrier).

Wetting agents, 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 quaternary ammonium compounds (for example cetyltrimethyl ammonium bromide), 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 es of sodium di-isopropyl- and tri-isopropyl-naphthalene ates), ether sulfates, alcohol ether es (for example sodium laurethsulfate), ether carboxylates (for example 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 e the reaction between lauryl alcohol and tetraphosphoric acid; additionally these ts may be ethoxylated), sulfosuccinamates, n 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 products of ne oxides, 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 d from long chain fatty acids or hexitol anhydrides; sation products of said partial esters with ethylene oxide; block polymers (comprising ethylene oxide and propylene oxide); alkanolamides; simple esters (for example fatty acid hylene glycol esters); amine oxides (for example lauryl yl amine oxide); and lecithins.

Suitable suspending agents include hydrophilic colloids (such as polysaccharides, polyvinylpyrrolidone or sodium carboxymethylcellulose) 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 g plant liable to infestation by the pests) or to any part of the plant, including the foliage, 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 culture systems), directly or it may be sprayed on, dusted on, applied by dipping, applied as a cream or paste formulation, applied as a vapor or applied through distribution or incorporation of a composition (such as a granular composition or a ition 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 ng techniques or other low volume methods, or applied by land or aerial irrigation systems.

Compositions for use as s preparations (aqueous solutions or dispersions) are generally ed 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 include DCs, SCs, ECs, EWs, MES, SGs, SPs, WPs, WGs and CSs, are often ed 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 applied by conventional spray equipment. Such aqueous preparations may contain varying amounts of a nd of the invention (for example 0.0001 to 10%, by weight) depending upon the purpose for which they are to be used.

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

The invention therefore also provides 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, herbicidal, insecticidal, nematicidal or idal activity.

The compound ofthe invention may be the sole active ingredient of the composition or it may be admixed with one or more additional active ingredients such as a pesticide, fungicide, ist, herbicide or plant growth tor where appropriate. An additional active ingredient may: provide a composition having a broader spectrum of ty or increased persistence at a locus; synergize the activity or complement the activity (for example by increasing the speed of effect or overcoming repellency) of the compound of the invention; or help to me or prevent the development of resistance to individual components. The particular additional active ingredient 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, erate, esfenvalerate, deltamethrin, cyhalothrin, lambda—cyhalothrin, gamma- thrin, hrin, fenpropathrin, cyfluthrin (including beta cyfluthrin), rin, ethofenprox, natural pyrethrin, ethrin, S-bioallethrin, fenfluthrin, prallethrin and -benzyl-3 -furylmethyl—(E)-(1R,3 S)-2,2-dimethyl- 3-(2—oxothiolanylidenemethyl)cyclopropane carboxylate; b) an organophosphate including those selected from the group consisting of sulprofos, acephate, methyl parathion, azinphos-methyl, n—s-methyl, heptenophos, thiometon, fenamiphos, monocrotophos, profenofos, triazophos, methamidophos, dimethoate, phosphamidon, malathion, chlorpyrifos, phosalone, terbufos, fensulfothion, fonofos, phorate, phoxim, pirimiphos-methyl, pirimiphos—ethyl, othion, azate and diazinon; c) a ate including those selected from the group ting of pirimicarb, triazamate, cloethocarb, carbofuran, furathiocarb, ethiofencarb, aldicarb, thiofurox, ulfan, bendiocarb, fenobucarb, propoxur, yl, thiodicarb and oxamyl; d) a benzoyl urea including those selected 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 pyrazole including those selected from the group consisting of tebufenpyrad 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 consisting of endosulfan (in ular alpha-endosulfan), benzene hexachloride, DDT, chlordane and dieldn'n; i) an amidine including those selected from the group consisting of chlordimeform and amitraz; j) a fumigant agent including those selected from the group consisting of chloropicrin, dichloropropane, methyl bromide and metam; k) a neonicotinoid compound including those selected from the group consisting of loprid, thiacloprid, acetamiprid, nitenpyram, dinotefuran, thiamethoxam, clothianidin, nithiazine and flonicamid; 1) a diacylhydrazine including those selected from the group consisting of tebufenozide, fenozide and yfenozide; m) a yl ether including those selected from the group consisting of diofenolan and pyriproxyfen; n) indoxacarb; o) chlorfenapyr; p) ozine; q) a tetramic acid compound including those selected from the group consisting of spirotetramat and iclofen, or a tetronic acid compound including spiromesifen; r) a diamide including those selected from the group consisting of flubendiamide, ntraniliprole (Rynaxypyr®) and cyantraniliprole; s) sulfoxaflor; t) mizone; u) fipronil and ethiprole; 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: 7 (WO 2006129714; W02011/147953; W02011/147952) ab) CAS: 269148 (WO 2007020986) In addition to the major chemical s of pesticide listed above, other pesticides having particular targets may be employed in the composition, if appropriate for the ed 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. atively insecticides or acaricides specific for particular insect species/stages may also be included in the compositions (for example acaricidal ovo-larvicides, such as clofentezine, flubenzimine, hexythiazox or tetradifon; acaricidal motilicides, such as dicofol or propargite; acaricides, such as ropylate or chlorobenzilate; or growth regulators, such as ethylnon, cyrornazine, methoprene, uazuron or diflubenzuron).

Examples of fungicidal compounds which may be included in the composition of the invention are (E)-N—methyl[2—(2,5-dimethylphenoxymethyl)phenyl]~2—methoxy-iminoacetamide (SSF-129), 4-bromo-2—cyano-N,N—dimethyltrifluoromethylbenzimidazole-l -sulfonamide, (3—chloro-2,6— —xylyl)—2—methoxyacetamido]—y—butyrolactone, 4—chloro—2-cyano-N,N-dimethyl—5-p—tolylimidazole-l - sulfonamide (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 carboxamide, acibenzolar (CGA245704), alanycarb, aldimorph, ine, azaconazole, azoxystrobin, benalaxyl, l, biloxazol, anol, blasticidin S, bromuconazole, bupirimate, ol, captan, dazim, 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 de l,l‘-dioxide, dichlofluanid, diclomezine, dicloran, diethofencarb, difenoconazole, difenzoquat, diflumetorim, 0,0-di-iso-propy1—S—benzyl thiophosphate, azole, dimetconazole, dimethomorph, dimethirimol, diniconazole, dinocap, dithianon, dodecyl dimethyl um chloride, rph, , doguadine, edifenphos, epoxiconazole, ethirimol, ethyl-(Z)-N—benzyl-N—([methyl(methyl-thioethylideneaminooxycarbonyl)amino]thio)—B-alaninate, etridiazole, famoxadone, fenamidone (RPA407213), fenarirnol, fenbuconazole, fenfuram, fenhexamid (KBR2738), fenpiclonil, pidin, fenpropimorph, fentin e, fentin hydroxide, ferbam, ferimzone, fluazinam, fludioxonil, flumetover, fluoroimide, fluquinconazole, flusilazole, flutolanil, flutriafol, folpet, fuberidazole, furalaxyl, tpyr, guazatine, hexaconazole, yisoxazole, hymexazole, imazalil, imibenconazole, iminoctadine, iminoctadine triacetate, zole, iprobenfos, iprodione, iprovalicarb (SZXO722), isopropanyl butyl carbamate, thiolane, kasugamycin, kresoxim-methyl, LY186054, LY211795, LY248908, mancozeb, maneb, mefenoxam, mepanipyrim, mepronil, metalaxyl, metconazole, metiram, metiram-zinc, metominostrobin, myclobutanil, neoasozin, nickel dimethyldithiocarbamate, nitrothal-z‘sopropyl, nuarimol, ofurace, mercury compounds, oxadixyl, oxasulfuron, oxolinic acid, oxpoconazole, oxycarboxin, pefurazoate, penconazole, pencycuron, phenazin oxide, phosetyl-Al, phosphorus acids, ide, picoxystrobin (ZAl963), poly- oxin D, polyram, probenazole, prochloraz, procymidone, propamocarb, propiconazole, propineb, propionic acid, pyrazophos, pyrifenox, pyrimethanil, pyroquilon, pyroxyfur, pyrrolnitrin, quaternary ammonium compounds, quinomethionate, quinoxyfen, quintozene, sipconazole ), sodium pentachlorophenate, spiroxamine, streptomycin, sulfur, tebuconazole, tecloftalam, tecnazene, tetraconazole, thiabendazole, thifluzamid, 2-(thiocyanomethylthio)benzothiazole, thiophanate-methyl, thiram, nconazole, tolclofos—methyl, uanid, triadimefon, triadimenol, triazbutil, triazoxide, tricyclazole, 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 l-1H—pyrazolecarboxamide [1072957-71 - l ], l-methyl-3 -difluoromethyl—lH-pyrazolecarboxylic acid (2-dichloromethylene—3-ethyl-l -methyl- 4-yl)-amide, and l-methyl-3 -difluoromethyl—4H—pyrazole—4—carboxylic acid [2-(2,4-dichlorophenyl )methoxy—l -methyl-ethyl]-amide.

Preferred additional pesticidally active ingredients are those selected from neonicotinoids, pyrethroids, 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 control 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 r embodiment the nd is a compound of formula II. In another embodiment the compound is a compound of formula III. In another embodiment the compound is a nd of formula IV. Preferably 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 t seed—borne, soil—home or foliar fungal diseases.

Examples of le synergists for use in the compositions include piperonyl butoxide, sesamex, safroxan and dodecyl imidazole.

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

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

Some mixtures may se active ingredients which have significantly different physical, chemical or ical properties such that they do not easily lend lves 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 nevertheless 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 mulsion (SE) formulation.

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.

Compositions of the invention include those prepared by ing prior to application, e.g. as a readymix or tankmix, or by simultaneous ation 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 results of a field trial to investigate control of Euschistus heros on soybeans with the compound of formula Ix ic 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 ation 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 nd of formula Ix (racemic es of enantiomers). The X axis indicates grams of active ingredient per e of (a) beta—cyfluthrin + imidacloprid, (b) thiamethoxam + lambda thrin, (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. Experimental details are indicated 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) idophos, (c) formula Iy at 60 g/ha, (d) formula Iy at 120 g/ha, (e) formula Ix at 60 g/ha, (f) a Ix at 120 g/ha. The Y axis indicates % control. Bars 1-5 show control after 2, 5, 7, 10 and 13 days after application respectively. Experimental details are indicated in Example 3.

Examples Example 1 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 60m2. The soybean was at growth stage bbch 72. The compound of formula Ix was applied as an EC formulation. The yfluthrin + 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.

Example 2 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 + 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 2 and represent the average of 3 replicates.

Example 3 Field trial: control of Euschz’stus heros on soybeans. ation was Foliar application using a rayer. 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 ation. The thiamethoxam + —cyhalothrin (21.2 g/ha and 28.2 g/ha respectively) was applied as a suspension concentrate formulation. The idophos was applied as a soluble concentrate formulation. The results (% control of adults) are shown in Figure 3 and represent the average 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 soybean 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 ity 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 ion are significantly more active against ugs than urally similar compounds, particularly 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., Retencao 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. Entomol. Brasil, 1978, 7, 85-98.

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

Schmidt, F. G. V., Fires, C. S. S., Sujii, E. R,., Borges, M,., Pantaleao, D. C., Lacerda, A. L., Azevedo, C. R., Comportamento e captura das fémeas de stus heros em armadilhas iscadas com feromonio sexual, 2003, Comunicado Te’cnico 93. Brasilia, DF.

Sosa-Gomez, 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), 216.

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

Claims (8)

What is claimed

1. A method comprising applying to a crop of soybean , 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 methyl; 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 nd of formula I as defined in claim 1 for control ofEuschistus.

3. A method or use ing 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, wherein 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 d in combination with one or more additional active ingredients selected from neonicotinoids, pyrethroids, strobilurins, triazoles and carboxamides.

6. A method or use according to any one of claims 1 to 5, wherein the nd 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 d in combination with an attractant selected from glucose, saccharose, salt, glutamate, citric acid, n 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