WO2013050317A1 - Formes polymorphes d'un dérivé d'isoxazoline - Google Patents

Formes polymorphes d'un dérivé d'isoxazoline Download PDF

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Publication number
WO2013050317A1
WO2013050317A1 PCT/EP2012/069325 EP2012069325W WO2013050317A1 WO 2013050317 A1 WO2013050317 A1 WO 2013050317A1 EP 2012069325 W EP2012069325 W EP 2012069325W WO 2013050317 A1 WO2013050317 A1 WO 2013050317A1
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compound
formula
spp
composition
mixture
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PCT/EP2012/069325
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English (en)
Inventor
Neil George
John Hone
Ian Kevin Jones
Rhea Brent
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Syngenta Limited
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Priority claimed from GBGB1117144.4A external-priority patent/GB201117144D0/en
Application filed by Syngenta Limited filed Critical Syngenta Limited
Publication of WO2013050317A1 publication Critical patent/WO2013050317A1/fr

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • This invention relates to solid forms of certain benzamide isoxazoline insecticides, to processes for their preparation, compositions comprising the solid forms and methods of their use as insecticides, acaricides, nematicides or molluscicides.
  • WO 2009/080250 discloses that certain isoxazoline compounds have insecticidal activity.
  • a compound of formula I is disclosed:
  • WO2011/104087 including as specific stereo-isomers, together with its use as a pesticide, in particular an insecticide, nematicide, molluscicide and acaricide, and pesticidal compositions containing it.
  • the present invention relates to novel crystalline forms of an isoxazoline insecticide of formula I:
  • the compound of formula I may be provided as a mixture with the alternative stereoisomer as a racemic mixture, or as an enantiomerically enriched mixture, e.g. in which the proportion of the compound of formula I compared to the total amount of the compound of formula I and the alternative stereoisomer is greater than 50%, e.g. at least 60%, 70%, 80%), 90%), 95%o or at least 99%>.
  • the compound of formula I may also be provided as a mixture with the trans sulfoxide isomer, e.g. in which the proportion of the compound of formula I compared to the total amount of the compound of formula I and the trans isomer is greater than 50%, e.g. at least 60%, 70%, 80%, 90%, 95% or at least 99%.
  • a crystalline polymorph of the compound of formula la i.e. the compound of formula I in the cis configuration
  • Form 1 which is characterised by the unit cell parameters of its single crystal as shown in Table 1.
  • This polymorph Form 1 is formed from either the R configuration of the compound of formula la or the S configuration. The polymorph was obtained using the method of Example la.
  • the polymorph of the compound of formula la designated Form 1 is characterised by a powder X-ray diffraction pattern expressed in terms of 2 ⁇ angles, wherein the powder X-ray diffraction pattern comprises at least three 2 ⁇ angle values (in degrees) selected from the group comprising 4.74 ⁇ 0.2, 16.98 ⁇ 0.2, 18.90 ⁇ 0.2, 23.54 ⁇ 0.2 and 29.94 ⁇ 0.2. More preferably, the powder X-ray diffraction pattern comprises all of these 2 ⁇ angle values. These 2 ⁇ angle values are derived from a powder X- ray diffraction pattern that has been calculated using data from the single crystal of the polymorph of the compound of formula la obtained using the method of Example la.
  • the values are generated using a wavelength of 1.54056A with a 2 ⁇ step size of 0.02°.
  • the polymorph of the compound of formula la designated Form 1 has a melting point of 198°C ⁇ 5°C. This melting point is obtained using Differential Scanning Calorimetry (DSC) with a heating rate of 10°C/minute.
  • DSC Differential Scanning Calorimetry
  • a polymorph of the compound of formula la that is a racemate of the R and S forms.
  • This polymorph designated Form 2
  • This polymorph is characterized by a powder X-ray diffraction pattern expressed in terms of 2 ⁇ angles, wherein the powder X- ray diffraction pattern comprises at least three 2 ⁇ angle values (in degrees) selected from the group comprising 12.27 ⁇ 0.2, 16.48 ⁇ 0.2, 18.78 ⁇ 0.2, 20.48 ⁇ 0.2 and 20.95 ⁇ 0.2. More preferably, the powder X-ray diffraction pattern comprises all of these 2 ⁇ angle values.
  • These 2 ⁇ angle values are derived from a powder X-ray diffraction pattern of polymorph Form 2 obtained using the method of Example lb. The values are measured using a wavelength of 1.54056A with a 2 ⁇ step size of 0.02°.
  • the polymorph of the compound of formula la designated Form 2 has a melting point of 198°C ⁇ 5°C. This melting point is obtained using Differential Scanning Calorimetry (DSC) with a heating rate of 10°C/minute.
  • DSC Differential Scanning Calorimetry
  • the present invention provides a further crystalline form of the compound of formula la, designated Form 3.
  • This polymorph is anhydrous and metastable.
  • This polymorph is characterised by the unit cell parameters of its single crystal as shown in Table 2 and is formed from either the R configuration of the compound of formula la or the S configuration. This polymorph was obtained using the method of Example la.
  • the polymorph of the compound of formula la designated Form 3 is characterised by a powder X-ray diffraction pattern expressed in terms of 2 ⁇ angles, wherein the powder X-ray diffraction pattern comprises at least three 2 ⁇ angle values (in degrees) selected from the group comprising 3.80 ⁇ 0.2, 4.82 ⁇ 0.2, 5.62 ⁇ 0.2, 6.61 ⁇ 0.2, 9.63 ⁇ 0.2, 11.28 ⁇ 0.2 and 13.23 ⁇ 0.2. More preferably, the powder X-ray diffraction pattern comprises all of these 2 ⁇ angle values.
  • These 2 ⁇ angle values are derived from a powder X-ray diffraction pattern that has been calculated using data from the single crystal of the polymorph of the compound of formula la obtained using the method of Example la. The values are generated using a wavelength of 1.54056A with a 2 ⁇ step size of 0.02°.
  • the polymorph of the compound of formula la designated Form 3 has a melting point of 185°C ⁇ 5°C. This melting point is obtained using Differential Scanning Calorimetry (DSC) with a heating rate of 10°C/minute.
  • DSC Differential Scanning Calorimetry
  • a polymorph is a particular crystal form of a chemical compound that can exist in more than one crystal form in the solid state.
  • a crystal form of a compound contains the constituent molecules arranged in orderly repeating patterns extending in all three spatial dimensions (in contrast, an amorphous solid form has no long-range order in the position of molecules).
  • Different polymorphs of a compound have different arrangements of atoms and or molecules in their crystal structure.
  • the compound is a biologically active compound, such as an insecticide
  • the difference in crystal structures can lead to different polymorphs having differing chemical, physical and biological properties. Properties which may be affected include crystal shape, density, hardness, colour, chemical stability, melting point, hydroscopicity, suspensibility, dissolution rate and biological availability.
  • a specific polymorph may have properties which make it more advantageous in a particular use relative to another polymorph of the same compound: in particular, the physical, chemical and biological properties listed above can have a significant effect on the development of production methods and formulations and the quality and efficacy of plant treatment agents, such as insecticides. It is noted that predicting whether the solid state of a compound may be present as more than one polymorph is not possible and nor is it possible to predict the properties of any of these crystal forms. In particular, in the context of the present invention, it has been found that the compound of formula la can exist as a stable polymorph designated Form 1 when present in either the S or the R configuration or as a stable polymorph designated Form 2 when present in a racemic form.
  • Both the Form 1 and Form 2 polymorphs are advantageous due to their stability which decreases the amount of crystallization occurring in formulations of the compound of formula I. Such crystallization is detrimental because it leads to thickening and potentially solidification of the formulation which can lead to blockages in application equipment e.g. in spray nozzles in agricultural application machinery.
  • the present invention also relates to methods for the preparation of the polymorphs of the invention either directly (i.e. not starting with other solid forms of the compound of formula la) or by conversion of other solid forms of the compound of formula la.
  • a method for preparing a crystalline polymorph of the compound of formula la designated Form 1 comprising i) providing a compound of formula Ia(S) or (R) which is completely dissolved in a solvent in which the compounds of formula la is sufficiently soluble to allow a solution of 0.5 to 10% w/v of the compound of formula la to be formed and then evaporating the solvent rapidly and then ii) adding a solvent which is suitable for forming a flowable slurry and maintaining the slurry at 25°C for 24 hours with stirring.
  • Suitable solvents for step i) include, but are not limited to, acetonitrile, methyl ethyl ketone, methanol or a mixture of any of these solvents with water.
  • Suitable solvents for step ii) include, but are not limited to, acetonitrile, methanol and mixtures of these solvents with water.
  • a method for preparing the crystalline polymorph designated Form 1 comprising mixing a compound of formula Ia(S) or Ia(R) in any form, crystalline or otherwise, with a solvent which is suitable for forming a flowable slurry, adding seed crystals of polymorph Form 1 to the slurry and maintaining the slurry whilst the compound of formula Ia(S) or Ia(R) converts to polymorph Form 1.
  • Suitable solvents include, but are not limited to, acetonitrile, methanol and mixtures of these solvents with water.
  • a method for preparing the crystalline polymorph designated Form 2 comprising i) providing a racemic mixture of the compound of formula la and a solvent in which the compounds of formula la is sufficiently soluble to allow a solution of 0.5 to 10% w/v of the compound of formula la to be formed ii) mixing the compound of formula la and the solvent such that at least some of the compound of formula la is present as a solid at 40°C and then iii) subjecting the mixture so formed to temperature cycling for at least three days, the temperature being cycled between about room temperature and 40°C every 4 hours with stirring.
  • Suitable solvents include, but are not limted to acetonitrile, methanol and mixtures of these solvents with water.
  • Assaying the solid phase for the presence of crystals may be carried out by conventional methods known in the art. For example, it is convenient and routine to use powder X-ray diffraction techniques. Other techniques which may be used include differential scanning calorimetry (DSC), thermo gravimetric analysis (TGA) and Raman or Infra-red spectroscopy, NMR, gas chromatography or HPLC. Single crystal X-ray diffraction is especially useful in identifying crystal structures.
  • the polymorphs of the invention may be readily incorporated into insecticidal compositions by conventional means. Accordingly, in a further aspect, the invention provides an insecticidal composition comprising a polymorph of the invention as defined above and an agriculturally acceptable carrier or diluent.
  • compositions of the invention to contain a mixture of the S and R configurations in any ratio, e.g. in a molar ratio of 1 :99 to 99: 1, the compositions of the invention may also comprise a racemic mixture of the compound of formula la in the S and R configurations or, preferably, be enantiomerically enriched for the compound of formula la in the S configuration.
  • the proportion of the S configuration compared to the total amount of both enantiomers is for example greater than 50mol%, e.g. at least 55, 60, 65, 70, 75, 80, 85, 90, 91, 92, 93, 94, 95, 96, 97, 98, or at least 99mol% of the combined amount of compound of formula I in the R and S configuration.
  • composition of the invention comprises a racemic mixture of the S and R configurations or is enantiomerically enriched for the compound of formula la in the S configuration
  • the composition may be made up of i) cis S polymorph Form 1 and cis R polymorph Form 1 or ii) racemic polymorph Form 2 or iii) a mixture thereof.
  • the composition of the invention comprises i) a crystalline polymorph of the compound of formula la designated Form 1, ii) a crystalline polymorph of the compound of formula la designated Form 2 or iii) a mixture thereof.
  • the composition further comprises at least one form of the compound of formula la which differs from Form 1 and Form 2, for example, Form 3 or an amorphous form or a mixture of Form 3 and the amorphous form.
  • the composition comprises less than about 20mol%, preferably less than about 10mol% and most preferably less than about 5mol%, of the at least one form of the compound of formula la which differs from Form 1 and Form 2.
  • the composition of the invention further comprises, in addition to the compound of formula la, the compound of formula lb.
  • the composition comprises less than about 25mol% of the compound of formula lb and more preferably less than about 20mol% of the compound of formula lb.
  • compositions comprising compounds of formula I are preferably enriched for compounds of formula I in the S configuration and preferably enriched for compounds of formula I in the cis configuration. Preferably said compositions are simultaneously enriched for compounds of formula I in the S configuration and cis configuration.
  • compositions comprising compounds of formula I may contain at least 70mol% of compounds Ia(S) and Ib(S) compared to the total amount of Ia(S), Ib(S), Ia(R) and Ib(R). In some cases said compositions contain at least 80mol%, at least 90mol%, or even at least 95mol% of compounds Ia(S) and Ib(S) compared to the total amount of Ia(S), Ib(S), Ia(R) and Ib(R). Compositions comprising compounds of formula I may contain at least 70mol% of compounds Ia(S) and Ia(R) compared to the total amount of Ia(S), Ib(S), Ia(R) and Ib(R).
  • compositions contain at least 80mol%, at least 90mol%, or even at least 95mol% of compounds Ia(S) and Ia(R) compared to the total amount of Ia(S), Ib(S), Ia(R) and Ib(R).
  • Compositions comprising compounds of formula I may contain at least 90mol% of compounds Ia(S) and Ib(S) compared to the total amount of compounds Ia(S), Ib(S), Ia(R) and Ib(R) and at least 60mol% of compounds Ia(S) and Ia(R) compared to the total amount of compounds Ia(S), Ib(S), Ia(R) and Ib(R).
  • Compositions comprising compounds of formula I may contain at least 90mol% of compounds Ia(S) and Ib(S) compared to the total amount of compounds Ia(S), Ib(S), Ia(R) and Ib(R) and at least 70mol% of compounds Ia(S) and Ia(R) compared to the total amount of compounds Ia(S), Ib(S), Ia(R) and Ib(R).
  • Compositions comprising compounds of formula I may contain at least 90mol% of compounds Ia(S) and Ib(S) compared to the total amount of compounds Ia(S), Ib(S), Ia(R) and Ib(R) and at least 80mol% of compounds Ia(S) and Ia(R) compared to the total amount of compounds Ia(S), Ib(S), Ia(R) and Ib(R).
  • Compositions comprising compounds of formula I may contain at least 90mol% of compounds Ia(S) and Ib(S) compared to the total amount of compounds Ia(S), Ib(S), Ia(R) and Ib(R) and at least 90mol% of compounds Ia(S) and Ia(R) compared to the total amount of compounds Ia(S), Ib(S), Ia(R) and Ib(R).
  • compositions comprising compounds of formula I may contain at least 70mol% of compounds Ia(S) and Ib(S) compared to the total amount of Ia(S), Ib(S), Ia(R) and Ib(R). In some cases said compositions contain at least 80mol%, at least 90mol%, or even at least 95mol% of compounds Ia(S) and Ib(S) compared to the total amount of Ia(S), Ib(S), Ia(R) and Ib(R). Compositions comprising compounds of formula I may contain at least 70mol% of compounds Ia(S) and Ia(R) compared to the total amount of Ia(S), Ib(S), Ia(R) and Ib(R).
  • compositions contain at least 80mol%, at least 90mol%, or even at least 95mol% of compounds Ia(S) and Ia(R) compared to the total amount of Ia(S), Ib(S), Ia(R) and Ib(R).
  • Compositions comprising compounds of formula I may contain at least 95mol% of compounds Ia(S) and Ib(S) compared to the total amount of compounds Ia(S), Ib(S), Ia(R) and Ib(R) and at least 60mol% of compounds Ia(S) and Ia(R) compared to the total amount of compounds Ia(S), Ib(S), Ia(R) and Ib(R).
  • Compositions comprising compounds of formula I may contain at least 95mol% of compounds Ia(S) and Ib(S) compared to the total amount of compounds Ia(S), Ib(S), Ia(R) and Ib(R) and at least 70mol% of compounds Ia(S) and Ia(R) compared to the total amount of compounds Ia(S), Ib(S), Ia(R) and Ib(R).
  • Compositions comprising compounds of formula I may contain at least 95mol% of compounds Ia(S) and Ib(S) compared to the total amount of compounds Ia(S), Ib(S), Ia(R) and Ib(R) and at least 80mol% of compounds Ia(S) and Ia(R) compared to the total amount of compounds Ia(S), Ib(S), Ia(R) and Ib(R).
  • Compositions comprising compounds of formula I may contain at least 95mol% of compounds Ia(S) and Ib(S) compared to the total amount of compounds Ia(S), Ib(S), Ia(R) and Ib(R) and at least 90mol% of compounds Ia(S) and Ia(R) compared to the total amount of compounds Ia(S), Ib(S), Ia(R) and Ib(R).
  • Compositions comprising compounds of formula I may contain at least 95mol% of compounds Ia(S) and Ib(S) compared to the total amount of compounds Ia(S), Ib(S), Ia(R) and Ib(R) and at least 95mol% of compounds Ia(S) and Ia(R) compared to the total amount of compounds Ia(S), Ib(S), Ia(R) and Ib(R).
  • polymorphs and compositions of the invention can be used to combat and control infestations of insect pests such as Lepidoptera, Diptera,
  • insects Hemiptera, Thysanoptera, Orthoptera, Dictyoptera, Coleoptera, Siphonaptera, Hymenoptera and Isoptera and also other invertebrate pests, for example, acarine, nematode and mollusc pests. Insects, acarines, nematodes and molluscs are hereinafter collectively referred to as pests.
  • the pests which may be combated and controlled by the polymorphs and compositions of the invention include those pests associated with agriculture (which term includes the growing of crops for food and fiber products), horticulture and animal husbandry, companion animals, forestry and the storage of products of vegetable origin (such as fruit, grain and timber); those pests associated with the damage of man-made structures and the transmission of diseases of man and animals; and also nuisance pests (such as flies).
  • compositions of the invention preferably wherein the compound of formula I is
  • coleopterans for example, Callosobruchus chinensis, Sitophilus zeamais, Tribolium castaneum, Epilachna
  • vigintioctomaculata Agriotes fuscicollis, Anomala rufocuprea, Leptinotarsa decemlineata, Diabrotica spp., Monochamus alternatus, Lissorhoptrus oryzophilus, Lyctus bruneus, Aulacophora femoralis; lepidopterans, for example, Lymantria dispar, Malacosoma neustria), Pieris rapae, Spodoptera litura, Mamestra brassicae, Chilo suppressalis),
  • Agrotisfucosa Galleria mellonella, Plutella maculipennis, Heliothis virescens, Phyllocnistis citrella; hemipterans, for example, Nephotettix cincticeps, Nilaparvata lugens,
  • orthopterans for example, Blatella germanica, Periplaneta americana, Gryllotalpa
  • Africana, Locusta migratoria migratoriodes Africana, Locusta migratoria migratoriodes; isopterans, for example, Reticulitermes speratus, Coptotermes formosanus; dipterans, for example, Musca domestica, Aedes aegypti, Hylemia platura, Culex pipiens, Anopheles sinensis, Culex tritaeniorhynchus, Liriomyza trifolii; acari, for example, Tetranychus cinnabarinus, Tetranychus urticae, Panonychus citri, Aculops pelekassi, Tarsonemus spp.
  • isopterans for example, Reticulitermes speratus, Coptotermes formosanus
  • dipterans for example, Musca domestica, Aedes aegypti, Hylemia platura, Culex pipiens, Anopheles sinensis, Cul
  • nematodes for example, Meloidogyne incognita, Bursaphelenchus lignicolus Mamiya et Kiyohara, Aphelenchoides besseyi, Heterodera glycines, Pratylenchus spp..
  • further pest species which may be controlled by the polymorphs and compositions of the invention (preferably wherein the compound of formula I is
  • Anoplura for example, Damalinia spp., Haematopinus spp., Linognathus spp., Pediculus spp., Trichodectes spp.; from the class of the Arachnida, for example, Acarus siro, Aceria sheldoni, Aculops spp., Aculus spp., Amblyomma spp., Argas spp., Boophilus spp., Brevipalpus spp., Bryobia praetiosa, Chorioptes spp., Dermanyssus gallinae,
  • Eotetranychus spp. Epitrimerus pyri, Eutetranychus spp., Eriophyes spp., Hemitarsonemus spp., Hyalomma spp., Ixodes spp., Latrodectus mactans, Metatetranychus spp., Oligonychus spp., Ornithodoros spp., Panonychus spp., Phyllocoptruta oleivora, Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Stenotarsonemus spp., Tarsonemus spp., Tetranychus spp., Vasates lycopersici; from the class of the Bivalva, for example, Dreissena spp.; from the order of the Chilopoda, for
  • Ceuthorhynchus spp. Ceuthorhynchus spp., Cleonus mendicus, Conoderus spp., Cosmopolites spp., Costelytra zealandica, Curculio spp., Cryptorhynchus lapathi, Dermestes spp., Diabrotica spp.,
  • Hyostrongulus spp. Loa Loa, Nematodirus spp., Oesophagostomum spp., Opisthorchis spp., Onchocerca volvulus, Ostertagia spp., Paragonimus spp., Schistosomen spp., Strongyloides fuelleborni, Strongyloides stercoralis, Stronyloides spp., Taenia saginata, Taenia solium, Trichinella spiralis, Trichinella nativa, Trichinella britovi, Trichinella nelsoni, Trichinella pseudopsiralis, Trichostrongulus spp., Trichuris trichuria, Wuchereria bancrofti; ft may be furthermore possible to control protozoa, such as Eimeria; from the order of the Heteroptera, for example, Anasa tristis, Antestiopsis spp., Blissus
  • Scotinophora spp. Stephanitis nashi, Tibraca spp., Triatoma spp.; from the order of the Homoptera, for example, Acyrthosipon spp., Aeneolamia spp., Agonoscena spp., Aleurodes spp., Aleurolobus barodensis, Aleurothrixus spp., Amrasca spp., Anuraphis cardui,
  • Aonidiella spp. Aphanostigma piri, Aphis spp., Arboridia apicalis, Aspidiella spp.,
  • Lepidoptera for example, Acronicta major, Aedia leucomelas, Agrotis spp., Alabama argillacea, Anticarsia spp., Barathra brassicae, Bucculatrix thurberiella, Bupalus piniarius, Cacoecia podana, Capua reticulana, Carpocapsa pomonella, Cheimatobia brumata, Chilo spp., Choristoneura fumiferana, Clysia ambiguella, Cnaphalocerus spp., Earias insulana, Ephestia kuehniella, Euproctis chrysorrhoea, Euxoa spp., Feltia spp., Galleria mellonella, Helicoverpa spp., Heliothis spp., Hofmannophila pseudospretella, Homona magnanima, Hyponomeu
  • Ceratophyllus spp., Xenopsylla cheopis From the order of the Symphyla, for example, Scutigerella immaculata; from the order of the Thysanoptera, for example, Basothrips biformis, Enneothrips flavens, Frankliniella spp., Heliothrips spp., Hercinothrips femoralis, Kakothrips spp., Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamoni, Thrips spp.; from the order of the Thysanura, for example, Lepisma saccharina.
  • the phytoparasitic nematodes include, for example, Anguina spp., Aphelenchoides spp.,
  • Heliocotylenchus spp. Heterodera spp., Longidorus spp., Meloidogyne spp., Pratylenchus spp., Radopholus similis, Rotylenchus spp., Trichodorus spp., Tylenchorhynchus spp., Tylenchulus spp., Tylenchulus semipenetrans, Xiphinema spp.
  • compositions and polymorphs of the invention may be used to control the following pest spcies:
  • Capsids Dysdercus spp. (capsids), Nilaparvata lugens (planthopper), Nephotettixc incticeps (leafhopper), Nezara spp. (stinkbugs), Euschistus spp. (stinkbugs), Leptocorisa spp.
  • decemlineata Cold potato beetle
  • Anthonomus grandis boll weevil
  • Aonidiella spp. scale insects
  • Trialeurodes spp. white flies
  • Bemisia tabaci white fly
  • Ostrinia nubilalis European corn borer
  • Spodoptera littoralis cotton leafworm
  • Heliothis virescens tobacco budworm
  • Helicoverpa armigera cotton bollworm
  • Helicoverpa zea cotton bollworm
  • Sylepta derogata cotton leaf roller
  • Pieris brassicae white butterfly
  • Plutella xylostella diamond back moth
  • Agrotis spp. cutworms
  • Chilo suppressalis rice stem borer
  • Locusta_ migratoria locust
  • Chortiocetes terminifera locust
  • Diabrotica spp. rootworms
  • Panonychus ulmi European red mite
  • Panonychus citri citrus red mite
  • Tetranychus urticae two-spotted spider mite
  • Tetranychus cinnabarinus carmine spider mite
  • Brevipalpus spp. flat mites
  • Boophilus microplus cattle tick
  • Dermacentor variabilis American dog tick
  • Ctenocephalides felis cat flea
  • Liriomyza spp. leafminer
  • Musca domestica housefly
  • Aedes aegypti mosquito
  • Anopheles spp. mosquitoes
  • Culex spp. mosquitoes
  • Pvhinotermitidae for example Coptotermes formosanus, Reticulitermes flavipes, R. speratu, R. virginicus, R. hesperus, and R. santonensis
  • Termitidae for example Globitermes sulfureus
  • Solenopsis geminata fire ant
  • Monomorium pharaonis pharaoh's ant
  • Damalinia spp. and Linognathus spp. bits and sucking lice
  • Meloidogyne spp. root knot nematodes
  • Globodera spp. Globodera spp.
  • Heterodera spp. cyst nematodes
  • the polymorphs and compositions of the invention of the invention may be used to control animal housing pests including: Ants, Bedbugs (adult), Bees, Beetles, Boxelder Bugs, Carpenter Bees, Carpet Beetles, Centipedes, Cigarette, Beetles, Clover Mites, Cockroaches, Confused Flour Beetle, Crickets, Earwigs, Firebrats, Fleas, Flies, Lesser Grain Borers, Millipedes, Mosquitoes, Red Flour Beetles, Rice Weevils, Saw- toothed Grain Beetles, Silverfish, Sowbugs, Spiders, Termites, Ticks, Wasps, Cockroaches, Crickets, Flies, Litter Beetles (such as Darkling, Hide, and Carrion), Mosquitoes, Pillbugs, Scorpions, Spiders, Spider Mites (Two
  • the polymorphs and compositions of the invention may be used to control ornamental pests including: Ants (Including Imported fire ants), Armyworms, Azalea caterpillars, Aphids, Bagworms, Black vine weevils (adult), Boxelder bugs,
  • Budworms California oakworms, Cankerworms, Cockroaches, Crickets, Cutworms, Eastern tent caterpillars, Elm leaf beetles, European sawflies, Fall webworms, Flea beetles, Forest tent caterpillars, Gypsy moth larvae, Japanese beetles (adults), June beetles (adults), Lace bugs, Leaf- feeding caterpillars, Leafhoppers, Leafminers (adults), Leaf rollers, Leaf skeletonizers, Midges, Mosquitoes, Oleander moth larvae, Pillbugs, Pine sawflies, Pine shoot beetles, Pinetip moths, Plant bugs, Root weevils, Sawflies, Scale insects (crawlers), Spiders, Spittlebugs, Striped beetles, Striped oakworms, Thrips, Tip moths, Tussock moth larvae, Wasps, Broadmites, Brown softscales, California redscales (crawlers), Clover mites
  • the polymorphs and compositions of the invention may be used to control turf pests including: Ants (Including Imported fire ants, Armyworms, Centipedes, Crickets, Cutworms, Earwigs, Fleas (adult), Grasshoppers, Japanese beetles (adult), Millipedes, Mites, Mosquitoes (adult), Pillbugs, Sod webworms, Sow bugs, Ticks (including species which transmit Lyme disease), Bluegrass billbugs (adult), Black turfgrass ataenius (adult), Chiggers, Fleas (adult), Grubs (suppression), Hyperodes weevils (adult), Mole crickets (nymphs and young adults), Mole Crickets (mature adults), Chinch Bugs.
  • Ants including Imported fire ants, Armyworms, Centipedes, Crickets, Cutworms, Earwigs, Fleas (adult), Grasshoppers, Japanese beetles (adult), Millipedes, Mit
  • the invention therefore provides a method of combating and controlling insects, acarines, nematodes or molluscs which comprises applying an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a polymorph or composition of the invention (preferably wherein the compound of formula I is simultaneously enriched for S and cis as defined above) to a pest, a locus of pest, preferably a plant, or to a plant susceptible to attack by a pest.
  • the polymorphs and compositions of the invention are preferably used against insects, acarines or nematodes.
  • plant as used herein includes seedlings, bushes and trees.
  • Plants are to be understood as also including those crops which have been rendered tolerant to herbicides or classes of herbicides (e.g. ALS-, GS-, EPSPS-, PPO- and HPPD- inhibitors) by conventional methods of breeding or by genetic engineering.
  • herbicides or classes of herbicides e.g. ALS-, GS-, EPSPS-, PPO- and HPPD- inhibitors
  • An example of a plant that has been rendered tolerant to imidazolinones, e.g. imazamox, by conventional methods of breeding is Clearfield® summer rape (canola).
  • Examples of plants that have been rendered tolerant to herbicides by genetic engineering methods include e.g. glyphosate- and glufosinate-resistant maize varieties commercially available under the trade names
  • Plants are also to be understood as being those which have been rendered resistant to harmful insects by genetic engineering methods, for example Bt maize (resistant to European corn borer), Bt cotton (resistant to cotton boll weevil) and also Bt potatoes (resistant to Colorado beetle).
  • Bt maize are the Bt 176 maize hybrids of NK® (Syngenta Seeds).
  • transgenic plants comprising one or more genes that code for an insecticidal resistance and express one or more toxins are KnockOut® (maize), Yield Gard® (maize), NuCOTIN33B® (cotton), Bollgard® (cotton), NewLeaf® (potatoes), NatureGard® and Protexcta®. Plants are also to be understood as being those which have been rendered resistant to harmful insects by genetic engineering methods, for example Bt maize (resistant to European corn borer), Bt cotton (resistant to cotton boll weevil) and also Bt potatoes
  • Examples of Bt maize are the Bt 176 maize hybrids of NK® (Syngenta Seeds).
  • Examples of transgenic plants comprising one or more genes that code for an insecticidal resistance and express one or more toxins are KnockOut® (maize), Yield Gard® (maize), NuCOTIN33B® (cotton), Bollgard® (cotton), NewLeaf® (potatoes), NatureGard® and Protexcta®.Plant crops or seed material thereof can be both resistant to herbicides and, at the same time, resistant to insect feeding ("stacked" transgenic events).
  • seed can have the ability to express an insecticidal Cry3 protein while at the same time being tolerant to glyphosate.
  • Traits include those that increase plant defences against insects, arachnids, nematodes and slugs and snails by virtue of toxins formed in the plants, in particular those formed in the plants by the genetic material from Bacillus thuringiensis (for example by the genes CrylA(Al), CrylA(b), CrylA(c), CryllA, CrylllA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb and CrylF and also combinations thereof).
  • Traits also include those that plant defences against fungi, bacteria and viruses by systemic acquired resistance (SA ), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins.
  • SA systemic acquired resistance
  • Plants or seed material thereof can be both resistant to herbicides and, at the same time, resistant to insect feeding ("stacked" transgenic events).
  • seed can have the ability to express an insecticidal Cry3 protein while at the same time being tolerant to glyphosate.
  • Plants are also to be understood as being those which are obtained by conventional methods of breeding or genetic engineering and contain so-called output traits (e.g. improved storage stability, higher nutritional value and improved flavor). Plants and plant cultivars obtained by genetic engineering methods, if appropriate in combination with conventional methods, and parts thereof, may be treated by the
  • 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.
  • the preferred transgenic plants or plant cultivars 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 products, better storage stability and/or processability of the harvested products. Further 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 increased tolerance of the plants to certain herbicidally active compounds.
  • transgenic plants which may be mentioned are the important crop plants, such as cereals (wheat, rice), maize, soya beans, potatoes, sugar beet, tomatoes, peas and other vegetable varieties, cotton, tobacco, oilseed rape and also fruit plants (with the fruits apples, pears, citrus fruits and grapes), and particular emphasis is given to maize, soya beans, potatoes, cotton, tobacco and oilseed rape.
  • the polymorphs and compositions of the invention may be used for pest control on various plants, including soybean (e.g. 10-70g/ha), corn (e.g. 10- 70g/ha), sugarcane (e.g. 20-200g/ha), alfalfa (e.g. 10-70g/ha), brassicas (e.g. 10-50g/ha), oilseed rape (e.g. canola) (e.g. 20-70g/ha), potatoes (including sweet potatoes) (e.g. 10- 70g/ha), cotton (e.g. 10-70g/ha), rice (e.g. 10-70g/ha), coffee (e.g.
  • citrus e.g. 60-200g/ha
  • almonds e.g. 40-180g/ha
  • fruiting vegetables e.g. tomatoes, pepper, chili, eggplant, cucumber, squash etc.
  • tea e.g. 20-150g/ha
  • bulb vegetables e.g. onion, leek etc.
  • grapes e.g. 30-180g/ha
  • pome fruit e.g. apples, pears etc.
  • stone fruit e.g. pears, plums etc.
  • the compound of formula I per se may be used for pest control on the various plants listed above.
  • the polymorphs and compositions of the invention may be used on soybean to control, for example, Elasmopalpus lignosellus (Dl), Diloboderus abderus (D2), Diabrotica speciosa (D3), Sternechus subsignatus (D4), Formicidae (D5), Agrotis ypsilon (D6), Julus ssp. (D7), Anticarsia gemmatalis (D8), Megascelis ssp. (D9), Procornitermes ssp.
  • D10 Gryllotalpidae (Dl 1), Nezara viridula (D12), Piezodorus spp. (D13), Acrosternum spp. (D14), Neomegalotomus spp. (D15), Cerotoma trifurcata (D16), Popillia japonica (D17), Edessa spp. (D18), Liogenys fuscus (D19), Euchistus hews (D20), stalk borer (D21), Scaptocoris castanea (D22), phyllophaga spp. (D23), Pseudoplusia includens (D24), Spodoptera spp.
  • the polymorphs and compositions of the invention are preferably used on soybean to control Diloboderus abderus, Diabrotica speciosa, Nezara viridula, Piezodorus spp., Acrosternum spp., Cerotoma trifurcata, Popillia japonica, Euchistus her os, phyllophaga spp., Agriotes spp..
  • the polymorphs and compositions of the invention may be used on corn to control, for example, Euchistus heros (D28), Dichelops furcatus (D29), Diloboderus abderus (D30), Elasmopalpus lignosellus (D31), Spodoptera frugiperda (D32), Nezara viridula (D33), Cerotoma trifurcata ponica (D34), Popillia japonica (D35), Agrotis ypsilon (D36), Diabrotica speciosa (D37), Heteroptera (D38), Procornitermes ssp.
  • D39 Scaptocoris castanea (D40), Formicidae (D41), Julus ssp. (D42), Dalbulus maidis (D43), Diabrotica virgifera (D44), Mods latipes (D45), Bemisia tabaci (D46), heliothis spp. (D47), Tetranychus spp. (D48), thrips spp. (D49), phyllophaga spp. (D50), scaptocoris spp. (D51), Liogenys fuscus (D52), Spodoptera spp. (D53), Ostrinia spp. (D54), Sesamia spp.
  • compositions and polymorphs of the invention are preferably used on corn to control Euchistus heros, Dichelops furcatus, Diloboderus abderus, Nezara viridula, Cerotoma trifurcata, Popillia japonica, Diabrotica speciosa, Diabrotica virgifera, Tetranychus spp., thrips spp., phyllophaga spp., scaptocoris spp., Agriotes spp..
  • compositions and compositions of the invention may be used on sugar cane to control, for example, Sphenophorus spp. (D57), termites (D58), Mahanarva spp. (D59).
  • the compositions and polymorphs of the invention are preferably used on sugar cane to control termites, Mahanarva spp..
  • the polymorphs and compositions of the invention may be used on alfalfa to control, for example, Hyper a brunneipennis (D60), Hyper a postica (D61), Colias eurytheme (D62), Collops spp. (D63), Empoasca solana (D64), Epitrix (D65), Geocoris spp. (D66), Lygus hesperus (D67), Lygus lineolaris (D68), Spissistilus spp. (D69), Spodoptera spp. (D70), Trichoplusia ni (D71).
  • D60 Hyper a brunneipennis
  • D61 Hyper a postica
  • D62 Colias eurytheme
  • Collops spp. D63
  • Empoasca solana D64
  • Epitrix D65
  • Geocoris spp. D66
  • Lygus hesperus D67
  • Lygus lineolaris D68
  • compositions and polymorphs of the invention are preferably used on alfalfa to control Hypera brunneipennis, Hypera postica, Empoasca solana, Epitrix, Lygus hesperus, Lygus lineolaris, Trichoplusia ni.
  • the polymorphs and compositions of the invention may be used on brassicas to control, for example, Plutella xylostella (D72), Pieris spp. (D73), Mamestra spp. (D74), Plusia spp. (D75), Trichoplusia ni (D76), Phyllotreta spp. (D77), Spodoptera spp. (D78), Empoasca solana (D79), thrips spp. (D80), Spodoptera spp. (D81), Delia spp. (D82).
  • Plutella xylostella D72
  • Pieris spp. D73
  • Mamestra spp. D74
  • Plusia spp. D75
  • Trichoplusia ni D76
  • Phyllotreta spp. D77
  • Spodoptera spp. D78
  • Empoasca solana D79
  • compositions and polymorphs of the invention are preferably used on brassicas to control Plutella xylostella Pieris spp. , Plusia spp. , Trichoplusia ni, Phyllotreta spp., thrips spp..
  • the polymorphs and compositions of the invention may be used on oil seed rape, e.g. canola, to control, for example, Meligethes sp. (D83),
  • Ceutorhynchus napi D84
  • Psylloides sp. D85
  • the polymorphs and compositions of the invention may be used on potatoes, including sweet potatoes, to control, for example, Empoasca sp. (D86), Leptinotarsa sp. (D87), Diabrotica speciosa (D88), Phthorimaea sp. (D89), Paratrioza sp. (D90), Maladera matrida (D91), Agriotes sp. (D92).
  • compositions and polymorphs of the invention are preferably used on potatoes, including sweet potatoes, to control Empoasca sp, Leptinotarsa sp, Diabrotica speciosa, Phthorimaea sp, Paratrioza sp, Agriotes sp.
  • the polymorphs and compositions of the invention may be used on cotton to control, for example, Anthonomus grandis (D93), Pectinophora sp. (D94), heliothis sp. (D95), Spodoptera sp. (D96), Tetranychus sp. (D97), Empoasca sp. (D98), thrips sp. (D99), Bemisia tabaci (D100), Lygus sp. (D101), phyllophaga sp. (D102), Scaptocoris sp. (D103).
  • Anthonomus grandis D93
  • Pectinophora sp. D94
  • heliothis sp. D95
  • Spodoptera sp. D96
  • Tetranychus sp. D97
  • Empoasca sp. D98
  • thrips sp. D99
  • Bemisia tabaci D100
  • compositions and polymorphs of the invention are preferably used on cotton to control Anthonomus grandis, Tetranychus sp, Empoasca sp, thrips sp, Lygus sp, phyllophaga sp, Scaptocoris sp.
  • the polymorphs and compositions of the invention may be used on rice to control, for example, Leptocorisa sp. (D104), Cnaphalocrosis sp. (D105), Chilo sp. (D106), Scirpophaga sp. (D107), Lissorhoptrus sp. (D108), Oebalus pugnax. (D109).
  • the compositions and polymorphs of the invention are preferably used on rice to control Leptocorisa sp, Lissorhoptrus sp, Oebalus pugnax.
  • the polymorphs and compositions of the invention may be used on coffee to control, for example, Hypothenemus Hampei (DUO), Perileucoptera Coffeella (Dl 11), Tetranychus sp. (Dl 12).
  • the compositions and polymorphs of the invention are preferably used on coffee to control Hypothenemus Hampei, Perileucoptera Coffeella.
  • the polymorphs and compositions of the invention may be used on citrus to control, for example, Panonychus citri (Dl 13), Phyllocoptruta oleivora (Dl 14), Brevipalpus sp. (Dl 15), Diaphorina citri (Dl 16), Scirtothrips sp. (Dl 17), thrips sp. (D118), Unaspis sp. (D119), Ceratitis capitata (D120), Phyllocnistis sp. (D121).
  • compositions and polymorphs of the invention are preferably used on citrus to control Panonychus citri, Phyllocoptruta oleivora, Brevipalpus sp, Diaphorina citri, Scirtothrips sp, thrips sp, Phyllocnistis sp.
  • polymorphs and compositions of the invention may be used on almonds to control, for example, Amyelois transitella (D122), Tetranychus sp.
  • the polymorphs and compositions of the invention may be used on fruiting vegetable, including tomatoes, pepper, chili, eggplant, cucumber, squash etc, to control thrips sp. (D124), Tetranychus sp. (D125), Polyphagotarsonemus sp. (D126),
  • Aculops sp. (D127), Empoasca sp. (D128), Spodoptera sp. (D129), heliothis sp. (D130), Tuta absoluta (D131), Liriomyza sp. (D132), Bemisia tabaci (D133), Trialeurodes sp. (D134), Paratrioza sp. (D135), Frankliniella occidentalis (D136), Frankliniella sp. (D137),
  • Anthonomus sp. (D138), Phyllotreta sp. (D139), Amrasca sp. (Dl 40), Epilachna sp. (D141), Halyomorpha sp. (D142), Scirtothrips sp. (D143), Leucinodes sp. (D144), Neoleucinodes sp. (D145).
  • compositions and polymorphs of the invention are preferably used on fruiting vegetable, including tomatoes, pepper, chili, eggplant, cucumber, squash etc, to control, for example, thrips sp, Tetranychus sp, Polyphagotarsonemus sp, Aculops sp, Empoasca sp, Spodoptera sp, heliothis sp, Tuta absolutea, Liriomyza sp, Paratrioza sp, Frankliniella occidentalis, Frankliniella sp, Amrasca sp, Scirtothrips sp, Leucinodes sp, Neoleucinodes sp.
  • the polymorphs and compositions of the invention may be used on tea to control, for example, Pseudaulacaspis sp. (D146), Empoasca sp. (D147), Scirtothrips sp. (D148), Caloptilia theivora (D149).
  • the compositions and polymorphs of the invention are prefrerably used on tea to control Empoasca sp, Scirtothrips sp.
  • the polymorphs and compositions of the invention may be used on bulb vegetables, including onion, leek etc to control, for example, thrips sp. (D150), Spodoptera sp. (D183), heliothis sp. (D151).
  • the compositions and polymorphs of the invention are preferably used on bulb vegetables, including onion, leek etc to control thrips sp.
  • polymorphs and compositions of the invention may be used on grapes to control, for example, Empoasca sp. (D152), Lobesia sp. (D153),
  • compositions and polymorphs of the invention are preferably used on grapes to control Frankliniella sp, thrips sp, Tetranychus sp, Rhipiphorothrips Cruentatus, Scaphoides sp.
  • polymorphs and compositions of the invention may be used on pome fruit, including apples, pairs etc, to control, for example, Cacopsylla sp.
  • compositions and polymorphs of the invention are preferably used on pome fruit, including apples, pears etc, to control Cacopsylla sp, Psylla sp, Panonychus ulmi.
  • the polymorphs and compositions of the invention (preferably wherein the compound of formula I is simultaneously enriched for S and cis as defined above) may be used on stone fruit to control, for example, Grapholita molesta (D166), Scirtothrips sp. (D167), thrips sp. (D168), FranklinieUa sp.
  • compositions and polymorphs of the invention are preferably used on stone fruit to control Scirtothrips sp, thrips sp, FranklinieUa sp, Tetranychus sp.
  • the polymorphs and compositions of the invention may be used on ornamental garden plants (e.g. flowers, shrubs, broad-leaved trees or evergreens), e.g. to control aphids (D171), whitefly (D172), scales (D173), meelybug (D174), beetles (D175) and caterpillars (D176).
  • ornamental garden plants e.g. flowers, shrubs, broad-leaved trees or evergreens
  • D173 e.g. to control aphids
  • D172 whitefly
  • scales D173
  • meelybug D174
  • beetles D175
  • caterpillars D176
  • the polymorphs and compositions of the invention may be used on garden plants (e.g. flowers, shrubs, broad-leaved trees or evergreens), on indoor plants (e.g. flowers and shrubs) and on indoor pest e.g. to control aphids (D177), whitefly (D178), scales (D179), meelybug (D180), beetles (D181) and caterpillars (D182).
  • garden plants e.g. flowers, shrubs, broad-leaved trees or evergreens
  • indoor plants e.g. flowers and shrubs
  • indoor pest e.g. to control aphids (D177), whitefly (D178), scales (D179), meelybug (D180), beetles (D181) and caterpillars (D182).
  • the compound of formula I per se may be used for pest control on the various plants listed above to control one or more plant diseases Dl to D183.
  • the polymorphs and compositions of the invention may be used on transgenic plants (including cultivars) obtained by genetic engineering methods and/or by conventional methods. These are understood as meaning plants having novel properties ("traits") which have been obtained by conventional breeding, by mutagenesis or by recombinant DNA techniques. 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.
  • the preferred transgenic plants or plant cultivars 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 products, better storage stability and/or processability of the harvested products.
  • transgenic plants which may be mentioned are the important crop plants, such as cereals (wheat, rice), maize, soybean, potatoes, sugar beet, tomatoes, peas and other vegetable varieties, cotton, tobacco, oilseed rape and also fruit plants (with the fruits apples, pears, citrus fruits and grapes).
  • polymorphs and compositions of the invention may be used on transgenic plants that are capable of producing one or more pesticidal proteins which confer upon the transgenic plant tolerance or resistance to harmful pests, e.g. insect pests, nematode pests and the like.
  • pesticidal proteins include, without limitation, Cry proteins from Bacillus thuringiensis CrylAb, CrylAc, CrylF, Cry2Ab, Cry2Ae, Cry3A, Cry3Bb, or Cry9C; engineered proteins such as modified Cry3A ( US Patent 7,030,295) or CrylA.105; or vegetative insecticidal proteins such as Vipl, Vip2 or Vip3.
  • Cry proteins from Bacillus thuringiensis CrylAb, CrylAc, CrylF, Cry2Ab, Cry2Ae, Cry3A, Cry3Bb, or Cry9C engineered proteins such as modified Cry3A ( US Patent 7,030,295) or CrylA.105
  • vegetative insecticidal proteins such as Vipl, Vip2 or Vip3.
  • pesticidal proteins useful in the invention include proteins of bacteria colonizing nematodes, e.g.
  • Photorhabdus spp. or Xenorhabdus spp. toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins, or other insect-specific neurotoxins; toxins produced by fungi, such Streptomycetes toxins, plant lectins, such as pea or barley lectins; agglutinins; proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors; ribosome-inactivating proteins (RIP), such as ricin, maize-RIP, abrin, luffin, saporin or bryodin; steroid metabolism enzymes, such as 3-hydroxysteroid oxidase, ecdysteroid-IDP-glycosyl-transferase, cholesterol oxidases, ecdysone inhibitors or HMG- CoA-reductase; ion channel blockers, such
  • Agrisure®CB (PI) (corn producing Cryl Ab), Agrisure®RW (P2) (corn producing mCry3A), Agrisure® Viptera (P3) (corn hybrids producing Vip3Aa); Agrisure300GT (P4) (corn hybrids producing Cryl Ab and mCry3A); YieldGard® (P5) (corn hybrids producing the Cryl Ab protein), YieldGard® Plus (P6) (corn hybrids producing Cryl Ab and Cry3Bbl), Genuity®
  • SmartStax® (P7) (corn hybrids with Cryl A.105, Cry2Ab2, CrylF, Cry34/35, Cry3Bb) ; Herculex® I (P8) (corn hybrids producing CrylFa) and Herculex®RW (P9) (corn hybrids producing Cry34Abl, Cry35Abl and the enzyme Phosphinothricin-N-Acetyltransferase [PAT]) ; NuCOTN®33B (P10) (cotton cultivars producing Cryl Ac), Bollgard®I (PI 1) (cotton cultivars producing Cryl Ac), Bollgard®II (PI 2) (cotton cultivars producing Cryl Ac and Cry2Ab2) and VIPCOT® (PI 3) (cotton cultivars producing a Vip3Aa). Soybean Cyst Nematode resistance soybean (SCN® - Syngenta (P 14)) and soybean with Aphid resistant trait (AMT® (PI 5)) are also of interest.
  • transgenic crops are: 1. Bill Maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St.
  • MIR604 Maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR 96/05/10 (P18). Maize which has been rendered insect-resistant by transgenic expression of a modified CrylllA toxin. This toxin is
  • Cry3A055 modified by insertion of a cathepsin-D-protease recognition sequence.
  • the preparation of such transgenic maize plants is described in WO 03/018810.
  • MON 863 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren, fil l 50 Brussels, Belgium, registration number C/DE/02/9 (PI 9). MON 863 expresses a CrylllB(bl) toxin and has resistance to certain Coleoptera insects.
  • NK603 x MON 810 Maize transgenically expresses the protein CP4 EPSPS, obtained from Agrobacterium sp. strain CP4, which imparts tolerance to the herbicide Roundup® (contains glyphosate), and also a CrylA(b) toxin obtained from
  • Bacillus thuringiensis subsp. kurstaki which brings about tolerance to certain Lepidoptera, include the European corn borer.
  • soybean plants carrying trains conferring resistance to 2.4D e.g. Enlist®
  • glyphosate e.g.
  • sulfonylurea e.g. STS®
  • glufosinate e.g. Liberty Link®, Ignite®
  • Dicamba e.g. isoxaflutole herbicide
  • 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).
  • cotton transgenic events include MON 531 / 757 / 1076 (Bollgard I ® - Monsanto), MON1445 (Roundup ready cotton ®- Monsanto), MON531 x MON1445 (Bollgard I + RR ®- Monsanto), MON15985 (Genuity Bollgard II cotton ®- Monsanto), MON88913 (Genuity RR FLEX cotton ®- Monsanto), MON15985 x MON1445 (Genuity Bollgard II + RR FELX cotton ®- Monsanto), MON15983 x MON88913 (Genuity Bollgard II + RR FLEX cotton ® - Monsanto), MON15985 (FibreMax Bollgard II Cotton ® - Monsanto), LL25 (FibreMax LL cotton ® - BCS Stoneville), GHB614 (FibreMax GlyTol cotton ®- BCS Stoneville),
  • COT102 x COT67B (Vipcot ® - Syngenta), COT102 x COT67B x MON88913 (Vipcot RR FLEX ® - Syngenta / Monsanto), 281-24-236 (Dow), 3006-210-23 (Dow), COT 102 (Syngenta), COT67B (Syngenta), T304-40 (BCS Stoneville).
  • Soy transgenic events include MON87701 x MON89788 (Genuity
  • Maize transgenic events include T25 (LibertyLink®, LL® - Bayerscropscience), DHT-1 (Dow), TC1507 (Herculex I® - Dow), DAS59122-7 (Herculex RW® - Dow), TC1507 + DAS59122-7 - Herculex Xtra® - Dow), TC1507 x DAS-59122-7 x NK603 (Herculex Xtra + RR® - Dow), TC1507 x DAS-59122- x MON88017 x
  • MON89034 (Genuity Smartstax corn®, Genuity Smartstax RIB complete® - Monsanto / Dow), MON89034 x NK603 (Genuity VT double PRO® - Monsanto), MON89034 + MON88017 (Genuity VT Triple PRO® - Monsanto), NK603 (Roundup Ready 2®, RR2® - Monsanto), MON810 (YieldGard BT®, Yieldgard cornborer® - Monsanto), MON810 x NK603 (YieldGard cornborer RR Corn 2® - Monasnto), MON810 x MON863 (YieldGard Plus® - Monsanto), MON863 x MON810 x NK603 (YieldGard Plus + RR Corn2® /
  • transgenic soybean e.g. P23 to P34
  • transgenic soybean e.g. P23 to P34
  • P34 is of particular interest, as well as the specific transgenic events listed above.
  • the polymorph or composition of the invention as an insecticide, acaricide, nematicide or molluscicide to a pest, a locus of pest, or to a plant susceptible to attack by a pest
  • the polymorph or composition of the invention as described above may be used in straight form but is usually formulated so that it further comprises a suitable inert diluent or carrier and, optionally, a wetting, dispersing and/or emulsifying agent or a surface active agent (SFA).
  • SFA surface active agent
  • 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, emulsification and wetting).
  • an interface for example, liquid/solid, liquid/air or liquid/liquid interfaces
  • other properties for example dispersion, emulsification and wetting.
  • 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, emulsification and wetting).
  • examples of such formulations are given on pages 35 to 39 of WO2011/104089 and below. It is preferred that all such formulated compositions (both solid and liquid formulations) comprise, by weight, 0.0001 to 95%, more preferably 1 to 85%, for example 5 to 60%, of the compound of formula I.
  • the formulated composition is generally used for the control of pests such that a compound of formula I is applied at a rate of from O. lg to 10kg per hectare, preferably from lg to 6kg per hectare, more preferably from lg to 1kg per hectare.
  • the compound of formula I per se may also be applied as described here.
  • the compound of formula I When used in a seed dressing, the compound of formula I is used at a rate of 0.000 lg to lOg (for example O.OOlg or 0.05g), preferably 0.005g to lOg, more preferably 0.005g to 4g, per kilogram of seed.
  • the formulations include from 0.01 to 90% by weight of active agent, from 0 to 20%> agriculturally acceptable surfactant and 10 to 99.99%) solid or liquid formulation inerts and adjuvant(s).
  • Concentrated forms of compositions generally contain in between about 2 and 80%>, preferably between about 5 and 70%> by weight of active agent.
  • Application forms of formulation may for example contain from 0.01 to 20% by weight, preferably from 0.01 to 5% by weight of active agent.
  • Commercial products will preferably be formulated as concentrates, the end user will normally employ diluted formulations.
  • Compositions of the compound of formula I with other active ingredients may, for example, be provided as a formulated product or may be mixed in a spray tank.
  • compositions may be employed in any conventional form, for example in the form of a twin pack, an emulsion concentrate (EC), a suspension concentrate (SC), a suspo-emulsion (SE), a capsule suspension (CS), a water dispersible granule (WG), an emulsifiable granule (EG), an emulsion, water in oil (EO), an emulsion, oil in water (EW), a micro-emulsion (ME), an oil dispersion (OD), an oil miscible flowable (OF), an oil miscible liquid (OL), a soluble concentrate (SL), an ultra-low volume suspension (SU), an ultra-low volume liquid (UL), a technical concentrate (TK), a dispersible concentrate (DC), a wettable powder (WP) or any technically feasible formulation in combination with agriculturally acceptable adjuvants.
  • EC emulsion concentrate
  • SC suspension concentrate
  • SE suspo-emulsion
  • CS capsule suspension
  • WG water dispersible granul
  • compositions used in any instance will depend upon the particular purpose envisaged and the physical, chemical and biological properties of the compound of formula I.
  • the formulated compositions are chosen from a number of formulation types, including dustable powders (DP), water dispersible granules (WG), wettable powders (WP), granules (GR) (slow or fast release), dispersible
  • DC suspension concentrates
  • SC suspension concentrates
  • aerosols fogging/smoke formulations
  • seed treatment formulations seed treatment formulations.
  • the formulation type chosen in any instance will depend upon the particular purpose envisaged.
  • Dustable powders may be prepared by mixing the compound of formula I 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 carriers) and mechanically grinding the mixture to a fine powder.
  • 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 carriers
  • WP Wettable powders
  • WG Water dispersible granules
  • Granules may be formed either by granulating a mixture of the compound of formula I and one or more powdered solid diluents or carriers, or from pre-formed blank granules by absorbing the compound of formula I (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 the compound of formula I (or a solution thereof, in a suitable agent) on to a hard core material (such as sands, silicates, mineral carbonates, sulfates or phosphates) and drying if necessary.
  • a porous granular material such as pumice, attapulgite clays, fuller's earth, kieselguhr, diatomaceous earths or ground corn cobs
  • a hard core material such as sands, silicates, mineral carbonates
  • Agents which are commonly used to aid absorption 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).
  • solvents such as aliphatic and aromatic petroleum solvents, alcohols, ethers, ketones and esters
  • 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).
  • DC Dispersible Concentrates
  • DC may be prepared by dissolving the compound of formula I in water or an organic solvent, such as a ketone, alcohol or glycol ether. These solutions may contain a surface active agent (for example to improve water dilution or prevent crystallization in a spray tank).
  • SC Suspension concentrates
  • SCs may comprise aqueous or non-aqueous suspensions of finely divided insoluble solid particles of the compound of formula I.
  • SCs may be prepared by ball or bead milling the solid compound of formula I in a suitable 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.
  • the compound of formula I may be dry milled and added to water, containing agents hereinbefore described, to produce the desired end product.
  • Aerosol formulations comprise the compound of formula I and a suitable propellant
  • the compound of formula I 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 suitable medium for example water or a water miscible liquid, such as n-propanol
  • the compound of formula I 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.
  • a composition may include one or more additives to improve the biological performance of the composition (for example by improving wetting, retention or distribution on surfaces; resistance to rain on treated surfaces; or uptake or mobility of the compound of formula I).
  • 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 the compound of formula I).
  • the compound of formula I may also be formulated for use as a seed treatment, for example as a powder composition, including a powder for dry seed treatment (DS), or a water dispersible powder for slurry treatment (WS).
  • DS powder for dry seed treatment
  • WS water dispersible powder for slurry treatment
  • 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 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
  • tetraphosphoric acid additionally these products may be ethoxylated
  • sulfosuccinamates may be ethoxylated
  • 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 products of alkylene 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 derived from long chain fatty acids or hexitol anhydrides; condensation products 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 suspending agents include hydrophilic colloids (such as polysaccharides, polyvinylpyrrolidone or sodium carboxymethylcellulose) and swelling clays (such as bentonite or attapulgite).
  • the compound of formula I and the compositions of the invention can be used for preventative, protectant and eradicant treatments and can be applied in a number of ways.
  • the compound of formula I and the compositions of the invention may be applied by any of the known means of applying pesticidal compounds.
  • they may be applied, formulated or unformulated, 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 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 composition packed in a water-soluble bag) in soil or an aqueous environment.
  • a locus of the pests such as a habitat of the pests, or a growing plant liable to infestation by the pests
  • the compound of formula I may also be injected into plants or trees or sprayed onto vegetation using electrodynamic spraying techniques or other low volume methods, or applied by land or aerial irrigation systems.
  • compositions for use as aqueous preparations are generally 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 include DCs, SCs, WPs and WGs , 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 applied by conventional spray equipment.
  • Such aqueous preparations may contain varying amounts of the compound of formula I (for example 0.0001 to 10%, by weight) depending upon the purpose for which they are to be used.
  • the compound of formula I can also be used in combination with other active ingredients, e.g.
  • the present invention also relates to a composition of the invention which comprises at least one further insecticide in addition to the compound of formula I and to compositions which comprise at least one further fungicide.
  • the present invention provides a composition of the invention which further comprises an insecticide (where "Tx" means a composition or polymorph of the invention, in particular those compositions described above that are simultaneously enriched for the S and cis configuration and which may result in a synergistic combination with the given active ingredient particularly at the ratios indicated below) which compositions are selected selected from: a) Pyrethroids, wherein suitable combinations include permethrin +Tx, cypermethrin +Tx, fenvalerate +Tx, esfenvalerate +Tx, deltamethrin +Tx, cyhalothrin +Tx (in particular lambda-cyhalothrin +Tx and gamma cyhalothrin +Tx), bifenthrin +Tx, fenpropathrin +Tx, cyfluthrin +Tx, tefluthrin +Tx, fish safe pyrethroids +Tx (where "
  • Carbamates including aryl carbamates
  • suitable combinations include pirimicarb +Tx, triazamate +Tx, cloethocarb +Tx, carbofuran +Tx, furathiocarb +Tx, ethiofencarb +Tx, aldicarb +Tx, thioiurox +Tx, carbosulfan +Tx, bendiocarb +Tx, fenobucarb +Tx, propoxur +Tx, methomyl +Tx or oxamyl +Tx;
  • Benzoyl ureas wherein suitable combinations include diflubenzuron +Tx, triflumuron +Tx, hexaflumuron +Tx, flufenoxuron +Tx, lufeneron +Tx or chlorfluazuron +Tx;
  • Organic tin compounds wherein suitable combinations include cyhexatin +Tx, fenbutatin oxide +Tx or azocyclotin +Tx;
  • Macrolides such as avermectins or milbemycins, wherein suitable combinations include for example abamectin +Tx, emamectin benzoate +Tx, ivermectin +Tx, milbemycin +Tx, spinosad +Tx, azadirachtin +Tx or spinetoram +Tx;
  • Hormones or pheromones are Hormones or pheromones
  • Organochlorine compounds wherein suitable combinations include endosulfan +Tx (in particular alpha-endosulfan +Tx), benzene hexachloride +Tx, DDT +Tx, chlordane +Tx or dieldrin +Tx;
  • Amidines wherein suitable combinations include chlordimeform +Tx or amitraz +Tx;
  • Fumigant agents wherein suitable combinations include chloropicrin +Tx, dichloropropane +Tx, methyl bromide +Tx or metam +Tx;
  • Neonicotinoid compounds wherein suitable combinations include imidacloprid +Tx, thiacloprid +Tx, acetamiprid +Tx, nitenpyram +Tx, dinotefuran +Tx, thiamethoxam +Tx, clothianidin +Tx or nithiazine +Tx;
  • Diacylhydrazines wherein suitable combinations include tebufenozide +Tx, chromafenozide +Tx or methoxyfenozide +Tx;
  • Diphenyl ethers wherein suitable combinations include diofenolan +Tx or pyriproxifen +Tx; combinations of Indoxacarb +Tx; combinations of Chlorfenapyr +Tx; combinations of Pymetrozine +Tx or flonicamid +Tx; combinations of pirotetramat +Tx, spirodiclofen +Tx or spiromesifen +Tx;
  • the further insecticide is selected from: pymetrozine; an organophosphate selected from the group consisting of sulprofos, acephate, methyl parathion, azinphos-methyl, demeton-s-methyl, heptenophos, thiometon, fenamiphos, monocrotophos, profenofos, triazophos, methamidophos, dimethoate, phosphamidon, malathion, chlorpyrifos, phosalone, terbufos, fensulfothion, fonofos, phorate, phoxim, pirimiphos-methyl, pirimiphos-ethyl, fenitrothion, fosthiazate and diazinon; a pyrethroid selected from the group consisting of permethrin, cypermethrin, fenvalerate, esfen
  • the compound of formula I is simultaneously enriched for S and cis as defined above and the insecticide is selected from the group consisting of abamectin, chlorpyrifos, cyantraniliprole, emamectin, lambda cyhalothrin, pymetrozine, spirotetramat, thiamethoxam, clothianidin, imidacloprid, chlorantraniliprole, flonicamid, sulfoxaflor, lufeneron, diafenthiuron, flubendiamide, tefluthrin, and fipronil.
  • the insecticide is selected from the group consisting of abamectin, chlorpyrifos, cyantraniliprole, emamectin, lambda cyhalothrin, pymetrozine, spirotetramat, thiamethoxam, clothianidin, imidacloprid, chlorantran
  • the insecticide is selected from the group consisting of abamectin, chlorpyrifos, cyantraniliprole, emamectin, lambda cyhalothrin, pymetrozine, spirotetramat, thiamethoxam, clothianidin, imidacloprid and flonicamid.
  • abamectin chlorpyrifos
  • cyantraniliprole cyantraniliprole
  • emamectin lambda cyhalothrin
  • pymetrozine spirotetramat
  • thiamethoxam clothianidin
  • imidacloprid and flonicamid imidacloprid and flonicamid.
  • the compound of formula I is simultaneously enriched for S and cis as defined above and the insecticide is selected from the group consisting of abamectin, chlorpyrifos, cyantraniliprole, emamectin, lambda cyhalothrin, pymetrozine, spirotetramat, thiamethoxam, clothianidin, imidacloprid and chlorantraniliprole.
  • the insecticide is selected from the group consisting of abamectin, chlorpyrifos, cyantraniliprole, emamectin, lambda cyhalothrin, pymetrozine, spirotetramat, thiamethoxam, clothianidin, imidacloprid and chlorantraniliprole.
  • the compound of formula I is simultaneously enriched for S and cis as defined above and the insecticide is selected from the group consisting of abamectin, chlorpyrifos, cyantraniliprole, emamectin, lambda cyhalothrin, pymetrozine, spirotetramat, and thiamethoxam.
  • insecticide is selected from the group consisting of abamectin, chlorpyrifos, cyantraniliprole, emamectin, lambda cyhalothrin, pymetrozine, spirotetramat, and thiamethoxam.
  • the active ingredients combinations described above comprising a polymorph or composition of the invention and an insecticide as described above are preferably combined in a mixing ratio of from 100: 1 to 1 :6000, especially from 50: 1 to 1 :50, more especially in a ratio of from 20 : 1 to 1 :20, even more especially from 10: 1 to 1 : 10, very especially from 5 : 1 to 1 :5, special preference being given to a ratio of from 2: 1 to 1 :2, and a ratio of from 4: 1 to 2: 1 being likewise preferred, above all in a ratio of 1 : 1, or 5: 1, or 5:2, or 5:3, or 5:4, or 4: 1, or 4:2, or 4:3, or 3: 1, or 3:2, or 2: 1, or 1 :5, or 2:5, or 3:5, or 4:5, or 1 :4, or 2:4, or 3:4, or 1 :3, or 2:3, or 1 :2, or 1 :600, or 1 :300, or 1 : 150, or 1 :35, or 2
  • compositions of the invention which further comprises a fungicide (where "Tx" means a composition or polymorph of the invention, in particular those compositions described above that are simultaneously enriched for the S and cis configuration, and which may result in a synergistic combination with the given active ingredient, particularly at the ratios indicated below) which compositions are selected selected from:
  • composition comprising a strobilurin fungicide including those selected from the group consisting of: Azoxystrobin +Tx, Dimoxystrobin+Tx, Enestrobin+Tx,
  • a composition comprising an azole fungicide including those selected from the group consisting of: Azaconazole+Tx, Bromuconazole+Tx, Cyproconazole+Tx,
  • Penconazole+Tx Penconazole+Tx, Prochloraz+Tx, Propiconazole+Tx, Prothioconazole+Tx,
  • Triadimenol+Tx Triflumizole+Tx, Triticonazole+Tx, Diclobutrazol+Tx,
  • Tridemorph+Tx, Fenpropidin+Tx and Spiroxamine+Tx f) a composition comprising a carboxamide fungicide including those selected from the group consisting of: Isopyrazam+Tx, Sedaxane+Tx, Bixafen+Tx, Penthiopyrad+Tx, Fluxapyroxad+Tx, Boscalid+Tx, Penflufen+Tx, Fluopyram+Tx, a compound of formula II+Tx
  • composition comprising a compound of formula III+Tx
  • composition comprising a compound of formula IV+Tx
  • composition comprising a carboxylic acid amide fungicide including those selected from the group consisting of: Mandipropamid+Tx, Benthiavalicarb+Tx and
  • composition comprising Chlorothalonil+Tx, Fluazinam+Tx, Dithianon+Tx,
  • the compound of formula I is simultaneously enriched for S and cis as defined above and the fungicide is selected from the group consisting of Azoxystrobin, Isopyrazam, Chlorothalonil, Cyproconazole, Difenoconazole,
  • the compound of formula I is simultaneously enriched for S and cis as defined above and the fungicide is selected from the group consisting of Azoxystrobin, Isopyrazam, Chlorothalonil, Cyproconazole, Difenoconazole, Mandipropamid, Mefenoxam, Metalaxyl, Sedaxane, Acibenzolar (including Acibenzolar-S- methyl), Fludioxonil, Cyprodinil, Penconazole, Propiconazole, Mancozeb, Prothioconazole, Pyraclostrobin, Boscalid, Bixafen, Fluopyram, Penthiopyrad, Thiabendazole, a compound of formula III and a compound of formula IV.
  • the fungicide is selected from the group consisting of Azoxystrobin, Isopyrazam, Chlorothalonil, Cyproconazole, Difenoconazole, Mandipropamid, Mefenoxam, Metalaxy
  • the compound of formula I is simultaneously enriched for S and cis as defined above and the fungicide is selected from the group consisting of Azoxystrobin, Isopyrazam, Chlorothalonil, Cyproconazole, Difenoconazole, Mandipropamid, Mefenoxam, Metalaxyl, Sedaxane, Acibenzolar (including Acibenzolar-S- methyl), Fludioxonil, Thiabendazole, a compound of formula III and a compound of formula IV and, most preferably, the fungicide is selected from the group consisting of Azoxystrobin, Isopyrazam, Chlorothalonil, Cyproconazole, Difenoconazole, Mandipropamid, Mefenoxam, a compound of formula III and a compound of formula IV.
  • Such combinations can give rise to synergistic effects at the ratios mentioned below.
  • the active ingredients combinations described above comprising a polymorph or composition of the invention and a fungicide as described above are preferably combined in a mixing ratio of from 100:1 to 1:6000, especially from 50:1 to 1:50, more especially in a ratio of from 20 : 1 to 1 :20, even more especially from 10:1 to 1:10, very especially from 5 : 1 to 1:5, special preference being given to a ratio of from 2: 1 to 1 :2, and a ratio of from 4: 1 to 2:1 being likewise preferred, above all in a ratio of 1:1, or 5:1, or 5:2, or 5:3, or 5:4, or 4:1, or 4:2, or 4:3, or 3:1, or 3:2, or 2:1, or 1:5, or 2:5, or 3:5, or 4:5, or 1:4, or 2:4, or 3:4, or 1:3, or 2:3, or 1:2, or 1:600, or 1:300, or 1:150, or 1:35, or 2:35, or 4:35, or 1:75, or 2:75, or
  • compositions comprising a compound of formula I and abamectin may be used to control one or more of plant diseases selected from Dl to D183 as described above, wherein the ratio of the compound of formula I to abamectin by weight in the composition is preferably 1 :0.05 to 1:1. Examples of ratios falling within this range include 1:0.1, 1 :0.2, 1:0.3, 1:0.4, 1:0.5, 1:0.6, 1:0.7, 1:0.8, 1:0.9. Where used for soil application the ratio of compound of formula I to abamectin may be up to 1 : 1.3, additional examples include 1:1.15, 1 : 1.2, 1 : 1.25. These compositions may also be used on transgenic plants, in particular those described above, in particular PI to P34. Transgenic soybean, e.g. P23 to P34, is of particular interest.
  • compositions comprising a compound of formula I and chlorpyrifos may be used to control one or more of plant diseases selected from Dl to D183 as described above, wherein the ratio of the compound of formula I to chlorpyrifos by weight in the composition is preferably 1:1 to 1:10. Examples of ratios falling within this range include 1:2, 1:3, 1:4, 1:5, 1 :6, 1 :7, 1 :8, 1 :9. These compositions may also be used on transgenic plants, in particular those described above, in particular PI to P34. Transgenic soybean, e.g. P23 to P34, is of particular interest.
  • compositions comprising a compound of formula I and cyantraniliprole may be used to control one or more of plant diseases selected from Dl to D 183 as described above, wherein the ratio of the compound of formula I to cyantraniliprole by weight in the composition is preferably 1 :0.2 to 1 :4. Examples of ratios falling within this range include 1:0.5, 1:1, 1:1.5, 1:2, 1:2.5, 1:3, 1:3.5.
  • These compositions may also be used on transgenic plants, in particular those described above, in particular PI to P34.
  • Transgenic soybean, e.g. P23 to P34 is of particular interest.
  • compositions comprising a compound of formula I and emamectin (preferably emamectin benzoate) may be used to control one or more of plant diseases selected from Dl to D 183 as described above, wherein the ratio of the compound of formula I to emamectin by weight in the composition is preferably 1 : 0.05 to 1 : 1. Examples of ratios falling within this range include 1 :0.1, 1 :0.2, 1 :0.3, 1 :0.4, 1 :0.5, 1 :0.6, 1 :0.7, 1 :0.8, 1 :0.9. These compositions may also be used on transgenic plants, in particular those described above, in particular PI to P34. Transgenic soybean, e.g.
  • compositions comprising a compound of formula I and lambda cyhalothrin may be used to control one or more of plant diseases selected from Dl to D 183 as described above, wherein the ratio of the compound of formula I to lambda cyhalothrin by weight in the composition is preferably 1 :0.1 to 1 :2. Examples of rates falling within this range include 1 :0.2, 1 :0.4, 1 :0.6, 1 :0.8, 1 : 1, 1 : 1.2, 1 : 1.4, 1 : 1.6, 1 :1.8. These compositions may also be used on transgenic plants, in particular those described above, in particular PI to P34. Transgenic soybean, e.g. P23 to P34, is of particular interest.
  • compositions comprising a compound of formula I and pymetrozine may be used to control one or more of plant diseases selected from Dl to D183 as described above, wherein the ratio of the compound of formula I to pymetrozine by weight in the composition is preferably 1 : 1 to 1 :6. Examples of rates falling within this range include 1 :2, 1 :3, 1 :4, 1 :5. Where used for soil application the ratio of compound of formula I to pymetrozine may be up to 1 : 10, additional examples include 1 :7, 1 :8, 1 :9. These compositions may also be used on transgenic plants, in particular those described above, in particular PI to P34. Transgenic soybean, e.g. P23 to P34, is of particular interest.
  • compositions comprising a compound of formula I and spirotetramat may be used to control one or more of plant diseases selected from Dl to D183 as described above, wherein the ratio of the compound of formula I to spirotetramat by weight in the composition is preferably 1 :0.5 to 1 :4. Examples of rates falling within this range include 1 :1, 1 : 1.5, 1 :2, 1 :2.5, 1 :3, 1 :3.5.
  • These compositions may also be used on transgenic plants, in particular those described above, in particular PI to P34.
  • Transgenic soybean, e.g. P23 to P34 is of particular interest.
  • compositions comprising a compound of formula I and thiamethoxam may be used to control one or more of plant diseases selected from Dl to D183 as described above, wherein the ratio of the compound of formula I to thiamethoxam by weight in the composition is preferably 1 : 0.5 to 1 :6. Examples of rates falling within this range include 1 : 1, 1 :2, 1 :3, 1 :4 and 1 :5.
  • These compositions may also be used on transgenic plants, in particular those described above, in particular PI to P34.
  • Transgenic soybean, e.g. P23 to P34 is of particular interest.
  • compositions comprising a compound of formula I and clothianidin may be used to control one or more of plant diseases selected from Dl to D183 as described above, wherein the ratio of the compound of formula I to clothianidin by weight in the composition is preferably 1 : 0.5 to 1 :6. Examples of rates falling within this range include 1 : 1, 1 :2, 1 :3, 1 :4 and 1 :5.
  • These compositions may also be used on transgenic plants, in particular those described above, in particular PI to P34.
  • Transgenic soybean, e.g. P23 to P34 is of particular interest.
  • compositions comprising a compound of formula I and imidacloprid may be used to control one or more of plant diseases selected from Dl to D183 as described above, wherein the ratio of the compound of formula I to imidacloprid by weight in the composition is preferably 1 : 0.5 to 1 :6. Examples of rates falling within this range include 1 : 1, 1 :2, 1 :3, 1 :4 and 1 :5.
  • These compositions may also be used on transgenic plants, in particular those described above, in particular PI to P34.
  • Transgenic soybean, e.g. P23 to P34 is of particular interest.
  • compositions comprising a compound of formula I and chlorantraniliprole may be used to control one or more of plant diseases selected from Dl to D 183 as described above, wherein the ratio of the compound of formula I to chlorantraniliprole by weight in the composition is preferably 1 :0.2 to 1 :4. Examples of ratios falling within this range include 1 :0.5, 1 : 1, 1 : 1.5, 1 :2, 1 :2.5, 1 :3, 1 :3.5. These compositions may also be used on transgenic plants, in particular those described above, in particular PI to P34. Transgenic soybean, e.g. P23 to P34, is of particular interest.
  • compositions comprising a compound of formula I and sulfoxaflor may be used to control one or more of plant diseases selected from Dl to D183 as described above, wherein the ratio of the compound of formula I to sulfoxaflor by weight in the composition is preferably 1 : 0.5 to 1 :6. Examples of rates falling within this range include 1 : 1, 1 :2, 1 :3, 1 :4 and 1 :5.
  • These compositions may also be used on transgenic plants, in particular those described above, in particular PI to P34.
  • Transgenic soybean, e.g. P23 to P34 is of particular interest.
  • compositions comprising a compound of formula I and azoxystrobin may be used to control one or more of plant diseases selected from Dl to D183 as described above, wherein the ratio of the compound of formula I to azoxystrobin by weight in the composition is preferably 1 : 1.5 to 1 : 10. Examples of ratios falling within this range include 1 :2, 1 :3, 1 :4, 1 :5, 1 :6, 1 :7, 1 :8, 1 :9. These compositions may also be used on transgenic plants, in particular those described above, in particular PI to P34. Transgenic soybean, e.g. P23 to P34, is of particular interest.
  • compositions comprising a compound of formula I and isopyrazam may be used to control one or more of plant diseases selected from Dl to D183 as described above, wherein the ratio of the compound of formula I to isopyrazam by weight in the composition is preferably 1 : 1 to 1 :3. Examples of ratios falling within this range include 1 : 1.5, 1 :2, 1 :2.5.
  • These compositions may also be used on transgenic plants, in particular those described above, in particular PI to P34. Transgenic soybean, e.g. P23 to P34, is of particular interest.
  • compositions comprising a compound of formula I and chlorothalonil may be used to control one or more of plant diseases selected from Dl to D183 as described above, wherein the ratio of the compound of formula I to chlorothalonil by weight in the composition is preferably 1 :5 to 1 :50. Examples of ratios falling within this range include 1 : 10, 1 : 15, 1 :20, 1 :25, 1 :30, 1 :35, 1 :40, 1 :45. These compositions may also be used on transgenic plants, in particular those described above, in particular PI to P34. Transgenic soybean, e.g. P23 to P34, is of particular interest.
  • compositions comprising a compound of formula I and cyproconazole may be used to control one or more of plant diseases selected from Dl to D183 as described above, wherein the ratio of the compound of formula I to cyproconazole by weight in the composition is preferably 1 : 1 to 1 :5. Examples of ratios falling within this range include 1 : 1.5, 1 :2, 1 :2.5, 1 :3, 1 :3.5, 1 :4, 1 :4.5. These compositions may also be used on transgenic plants, in particular those described above, in particular PI to P34. Transgenic soybean, e.g. P23 to P34, is of particular interest.
  • compositions comprising a compound of formula I and difenoconazole may be used to control one or more of plant diseases selected from Dl to D183 as described above, wherein the ratio of the compound of formula I to difenoconazole by weight in the composition is preferably 1 :0.3 to 1 :5. Examples of ratios falling within this range include 1 :0.5, 1 :0.7, 1 :0.9, 1 : 1, 1 : 1.2, 1 : 1.4. These compositions may also be used on transgenic plants, in particular those described above, in particular PI to P34. Transgenic soybean, e.g. P23 to P34, is of particular interest.
  • compositions comprising a compound of formula I and mandipropamid may be used to control one or more of plant diseases selected from Dl to D 183 as described above, wherein the ratio of the compound of formula I to mandipropamid by weight in the composition is preferably 1 : 1 to 1 : 15. Examples of ratios falling within this range include 1 :2, 1 :4, 1 :6, 1 :8, 1 : 10, 1 : 12, 1 : 14. These compositions may also be used on transgenic plants, in particular those described above, in particular PI to P34. Transgenic soybean, e.g. P23 to P34, is of particular interest.
  • compositions comprising a compound of formula I and mefenoxam may be used to control one or more of plant diseases selected from Dl to D183 as described above, wherein the ratio of the compound of formula I to mefenoxam by weight in the composition is preferably 1 :0.3 to 1 :8. Examples of ratios falling within this range include 1 : 1, 1 :2, 1 :3, 1 :4, 1 :5, 1 :6, 1 :7.
  • These compositions may also be used on transgenic plants, in particular those described above, in particular PI to P34.
  • Transgenic soybean, e.g. P23 to P34 is of particular interest.
  • compositions comprising a compound of formula I and a compound of formula II
  • compositions may be used to control one or more of plant diseases selected from Dl to D 183 as described above, wherein the ratio of the compound of formula I to the compound of formula II by weight in the composition is preferably 1 :0.3 to 1 :8. Examples of ratios falling within this range include 1 : 1, 1 :2, 1 :3, 1 :4, 1 :5, 1 :6, 1 :7.
  • These compositions may also be used on transgenic plants, in particular those described above, in particular PI to P34.
  • Transgenic soybean, e.g. P23 to P34 is of particular interest.
  • compositions comprising a compound of formula I and a compound of formula III
  • compositions may be used to control one or more of plant diseases selected from Dl to D 183 as described above, wherein the ratio of the compound of formula I to the compound of formula III by weight in the composition is preferably 1 :0.3 to 1 :8. Examples of ratios falling within this range include 1 : 1, 1 :2, 1 :3, 1 :4, 1 :5, 1 :6, 1 :7. .
  • These compositions may also be used on transgenic plants, in particular those described above, in particular PI to P34.
  • Transgenic soybean, e.g. P23 to P34 is of particular interest.
  • Abamectin, chlorpyrifos, cyantraniliprole, emamectin, lambda cyhalothrin, pymetrozine, spirotetramat, thiamethoxam, clothianidin, imidacloprid, chlorantraniliprole, azoxystrobin, isopyrazam, chlorothalonil, cyproconazole, difenoconaozle, mandipropamid and mefenoxam are well known pesticides and are described for example in The Pesticide Manual - A World Compendium; Fifteenth Edition; Editor: C. D. S. Tomlin; The British Crop Protection Council.
  • the compound of formula II is known from WO 2007/048556, the compound of formula III is known from WO 2010/000612. It is known e.g. from WO2011/104088 and WO2011/104087, that combinations of compounds of formula I and these active ingredients gives rise to synergistic control, as defined by the Colby formula.
  • compositions and polymorphs of the invention are also useful in the field of animal health, e.g. they may be used against parasitic invertebrate pests, more preferably against parasitic invertebrate pests in or on an animal.
  • pests include nematodes, trematodes, cestodes, flies, mites, tricks, lice, fleas, true bugs and maggots.
  • the animal may be a non-human animal, e.g. an animal associated with agriculture, e.g. a cow, a pig, a sheep, a goat, a horse, or a donkey, or a companion animal, e.g.
  • the invention provides a composition or polymorph of the invention (preferably wherein the compound of formula I is simultaneously enriched for S and cis as defined above) for use in a method of therapeutic treatment.
  • the invention relates to a method of controlling parasitic invertebrate pests in or on an animal comprising administering a pesticidally effective amount of a composition or polymorph of the invention.
  • the administration may be for example oral administration, parenteral administration or external administration, e.g. to the surface of the animal body.
  • the invention relates to a composition or polymorph of the invention for controlling parasitic invertebrate pests in or on an animal.
  • the invention relates to use of a composition or polymorph of the invention in the manufacture of a medicament for controlling parasitic invertebrate pests in or on an animal
  • the invention provides a pharmaceutical composition
  • a pharmaceutical composition comprising a composition or polymorph of the invention (preferably wherein the compound of formula I is simultaneously enriched for S and cis as defined above) and a pharmaceutically suitable excipient.
  • the compositions and polymorphs of the invention may be used alone or in combination with one or more other biologically active ingredients.
  • compositions of the invention are preferably selected from (where "Tx" means a composition or polymorph of the invention, in particular those compositions described above that are simultaneously enriched for the S and cis configuration, and which may result in a synergistic combination with the given active ingredient, particularly at the ratios indicated below) imidacloprid + Tx, enrofloxacin + Tx, praziquantel + Tx, pyrantel embonate + Tx, febantel + Tx, penethamate + Tx, moloxicam + Tx, cefalexin + Tx, kanamycin + Tx, pimobendan + Tx, clenbuterol + Tx, fipronil + Tx, ivermectin + Tx, omeprazole + Tx, tiamulin + Tx, benazepril + Tx, milbemycin + Tx, cyromazine + Tx, thiame
  • ratios include 100: 1 to 1 :6000, 50: 1 to 1 :50, 20: 1 to 1 :20, even more especially from 10: 1 to 1 : 10, 5: 1 to 1 :5, 2: 1 to 1 :2, 4: 1 to 2: 1, 1 : 1, or 5: 1, or 5:2, or 5:3, or 5:4, or 4: 1, or 4:2, or 4:3, or 3: 1, or 3:2, or 2: 1, or 1 :5, or 2:5, or 3:5, or 4:5, or 1 :4, or 2:4, or 3:4, or 1 :3, or 2:3, or 1 :2, or 1 :600, or 1 :300, or 1 : 150, or 1 :35, or 2:35, or 4:35, or 1 :75, or 2:75, or 4:75, or 1 :6000, or 1 :3000, or 1 : 1500, or 1 :350, or 2:350, or 4:350, or 1 :750, or 2:750, or 4:750,
  • a combination product of the invention may comprise a pesticidally effective amount of a compound of formula I and pesticidally effective amount of at least one additional parasitic invertebrate pest control active ingredient having a similar spectrum of control but a different site of action.
  • salts of chemical compounds are in equilibrium with their corresponding non salt forms, salts share the biological utility of the non salt forms.
  • compositions and polymorphs of the invention may be suitable for combating parasitic invertebrate pests that infest companion animals and pets (e.g., dogs, cats, pet birds and aquarium fish), research and experimental animals (e.g., hamsters, guinea pigs, rats and mice), as well as animals raised for/in zoos, wild habitats and/or circuses.
  • companion animals and pets e.g., dogs, cats, pet birds and aquarium fish
  • research and experimental animals e.g., hamsters, guinea pigs, rats and mice
  • animals raised for/in zoos wild habitats and/or circuses.
  • the animal is preferably a vertebrate, and more preferably a mammal, avian or fish.
  • the animal subject is a mammal (including great apes, such as humans).
  • Other mammalian subjects include primates (e.g., monkeys), bovine (e.g., cattle or dairy cows), porcine (e.g., hogs or pigs), ovine (e.g., goats or sheep), equine (e.g., horses), canine (e.g., dogs), feline (e.g., house cats), camels, deer, donkeys, buffalos, antelopes, rabbits, and rodents (e.g., guinea pigs, squirrels, rats, mice, gerbils, and hamsters).
  • primates e.g., monkeys
  • bovine e.g., cattle or dairy cows
  • porcine e.g., hogs or pigs
  • ovine
  • Anatidae such as swans, geese, and ducks
  • Columbidae such as doves and domestic pigeons
  • Phasianidae such as partridge, grouse and turkeys
  • Thesienidae such as domestic chickens
  • Psittacines such as parakeets, macaws and parrots raised for the pet or collector market, among others.
  • fish is understood to include without limitation, the Teleosti grouping of fish, i.e., teleosts. Both the Salmoniformes order (which includes the Salmonidae family) and the Perciformes order (which includes the Centrarchidae family) are contained within the Teleosti grouping. Examples of potential fish recipients include the Salmonidae, Serranidae, Sparidae, Cichlidae, and Centrarchidae, among others.
  • inventions are also contemplated to benefit from the inventive methods, including marsupials (such as kangaroos), reptiles (such as farmed turtles), and other economically important domestic animals for which the inventive methods are safe and effective in treating or preventing parasite infection or infestation.
  • marsupials such as kangaroos
  • reptiles such as farmed turtles
  • other economically important domestic animals for which the inventive methods are safe and effective in treating or preventing parasite infection or infestation.
  • Examples of parasitic invertebrate pests controlled by administering a pesticidally effective amount of the compositions and polymorphs of the invention to an animal to be protected include ectoparasites (arthropods, acarines, etc.) and endoparasites (helminths, e.g., nematodes, trematodes, cestodes, acanthocephalans, etc. and protozoae, such as coccidia).
  • helminthiasis The disease or group of diseases described generally as helminthiasis is due to infection of an animal host with parasitic worms known as helminths.
  • helminths The term 'helminths' is meant to include nematodes, trematodes, cestodes and acanthocephalans.
  • Helminthiasis is a prevalent and serious economic problem with domesticated animals such as swine, sheep, horses, cattle, goats, dogs, cats and poultry.
  • Nematodes that are contemplated to be treated by the compositions and polymorphs of the invention (preferably wherein the compound of formula I is simultaneously enriched for S and cis as defined above) include, without limitation, the following genera:
  • Dioctophyme Dipetalonema, Diphyllobothrium, Dirofilaria, Dracunculus, Enterobius, Filaroides, Haemonchus, Heterakis, Lagochilascaris, Loa, Mansonella, Muellerius, Necator, Nematodirus, Oesophagostomum, Ostertagia, Oxyuris, Parafilaria, Parascaris,
  • Dictyocaulus are found in the lungs. Still other parasites may be located in other tissues such as the heart and blood vessels, subcutaneous and lymphatic tissue and the like.
  • Trematodes that are contemplated to be treated by the invention and by the inventive methods include, without limitation, the following genera: Alaria, Fasciola, Nanophyetus, Opisthorchis, Paragonimus and Schistosoma.
  • Cestodes that are contemplated to be treated by the invention and by the inventive methods include, without limitation, the following genera: Diphyllobothrium, Diplydium, Spirometra and Taenia.
  • the most common genera of parasites of the gastrointestinal tract of humans are
  • Enterobius Other medically important genera of parasites which are found in the blood or other tissues and organs outside the gastrointestinal tract are the filarial worms such as Wuchereria, Brugia, Onchocerca and Loa, as well as Dracunculus and extra intestinal stages of the intestinal worms Strongyloides and Trichinella.
  • helminth genera and species are known to the art, and are also contemplated to be treated by the compositions and polymorphs of the invention. These are enumerated in great detail in Textbook of Veterinary Clinical Parasitology, Volume 1, Helminths, E. J. L. Soulsby, F. A. Davis Co., Philadelphia, Pa.; Helminths, Arthropods and Protozoa, (6 th Edition of Monnig's Veterinary Helminthology and Entomology), E. J. L. Soulsby, Williams and Wilkins Co., Baltimore, Md.
  • compositions and polymorphs of the invention may be effective against a number of animal ectoparasites (e.g., arthropod ectoparasites of mammals and birds in particular insects such as flies (stinging and licking), parasitic fly larvae, lice, hair lice, bird lice, fleas and the like; or acarids, such as ticks, for examples hard ticks or soft ticks, or mites, such as scab mites, harvest mites, bird mites and the like).
  • insects such as flies (stinging and licking), parasitic fly larvae, lice, hair lice, bird lice, fleas and the like
  • acarids such as ticks, for examples hard ticks or soft ticks, or mites, such as scab mites, harvest mites, bird mites and the like.
  • Insect and acarine pests include, e.g., biting insects such as flies and mosquitoes, mites, ticks, lice, fleas, true bugs, parasitic maggots, and the like.
  • Adult flies include, e.g., the horn fly or Haematobia irritans, the horse fly or
  • Tabanus spp. the stable fly or Stomoxys calcitrans, the black fly or Simulium spp., the deer fly or Chrysops spp., the louse fly or Melophagus ovinus, and the tsetse fly or Glossina spp.
  • Parasitic fly maggots include, e.g., the bot fly ⁇ Oestrus ovis and Cuterebra spp.), the blow fly or Phaenicia spp., the screwworm or Cochliomyia hominivorax, the cattle grub or
  • Mosquitoes include, for example, Culex spp., Anopheles spp. and Aedes spp.
  • Mites include Mesostigmalphatalpha spp. e.g., mesostigmatids such as the chicken mite, Dermalphanyssus galphallinalphae; itch or scab mites such as Sarcoptidae spp. for example, Salpharcoptes scalphabiei; mange mites such as Psoroptidae spp. including Chorioptes bovis and Psoroptes ovis; chiggers e.g., Trombiculidae spp. for example the North American chigger, Trombiculalpha alphalfreddugesi.
  • Ticks include, e.g., soft-bodied ticks including Argasidae spp. for example Argalphas spp. and Ornithodoros spp.; hard-bodied ticks including Ixodidae spp., for example
  • Lice include, e.g., sucking lice, e.g., Menopon spp.
  • biting lice e.g., Haematopinus spp., Linognathus spp. and Solenopotes spp.
  • Fleas include, e.g., Ctenocephalides spp., such as dog flea (Ctenocephalides canis) and cat flea ⁇ Ctenocephalides felis); Xenopsylla spp. such as oriental rat flea (Xenopsylla cheopis); and Pulex spp. such as human flea (Pulex irritans).
  • Ctenocephalides spp. such as dog flea (Ctenocephalides canis) and cat flea ⁇ Ctenocephalides felis
  • Xenopsylla spp. such as oriental rat flea (Xenopsylla cheopis)
  • Pulex spp. such as human flea (Pulex irritans).
  • True bugs include, e.g., Cimicidae or e.g., the common bed bug (Cimex lectularius); Triatominae spp. including triatomid bugs also known as kissing bugs; for example
  • flies, fleas, lice, mosquitoes, gnats, mites, ticks and helminths cause tremendous losses to the livestock and companion animal sectors.
  • Arthropod parasites also are a nuisance to humans and can vector disease-causing organisms in humans and animals.
  • compositions and polymorphs of the invention may also be effective against ectoparasites, e.g. insects such as flies (stinging and licking), parasitic fly larvae, lice, hair lice, bird lice, fleas and the like; or acarids, such as ticks, for examples hard ticks or soft ticks, or mites, such as scab mites, harvest mites, bird mites and the like.
  • insects e.g. insects such as flies (stinging and licking), parasitic fly larvae, lice, hair lice, bird lice, fleas and the like; or acarids, such as ticks, for examples hard ticks or soft ticks, or mites, such as scab mites, harvest mites, bird mites and the like.
  • flies such as Haematobia (Lyperosia) irritans (horn fly), Simulium spp. (blackfly), Glossina spp.
  • Gastrophilus nasalis lice such as Bovicola (Damalinia) bovis, Bovicola equi, Haematopinus asini, Felicola subrostratus, Heterodoxus spiniger, Lignonathus setosus and Trichodectes canis; keds such as Melophagus ovinus; and mites such as Psoroptes spp., Sarcoptes scabei, Chorioptes bovis, Demodex equi, Cheyletiella spp., Notoedres cati, Trombicula spp. and Otodectes cyanotis (ear mites).
  • Treatments of the invention are by conventional means such as by enteral administration in the form of, for example, tablets, capsules, drinks, drenching preparations, granulates, pastes, boli, feed-through procedures, or suppositories; or by parenteral administration, such as, for example, by injection (including intramuscular, subcutaneous, intravenous, intraperitoneal) or implants; or by nasal administration; or by dermal application in the form of, for example, bathing or dipping, spraying, pouring-on and spotting-on, washing, dusting, and with the aid of active-compound-comprising shaped articles such as collars, ear tags, tail tags, limb bands, halters, marking devices and the like.
  • enteral administration in the form of, for example, tablets, capsules, drinks, drenching preparations, granulates, pastes, boli, feed-through procedures, or suppositories
  • parenteral administration such as, for example, by injection (including intramuscular, subcutaneous,
  • compositions and polymorphs of the invention When compositions and polymorphs of the invention are applied in combination with an additional biologically active ingredient, they may be administered separately e.g. as separate compositions. In this case, the biologically active ingredients may be administered simultaneously or sequentially. Alternatively, the biologically active ingredients may be components of one composition.
  • compositions and polymorphs of the invention may be administered in a controlled release form, for example in subcutaneous or orally adminstered slow release formulations.
  • a parasiticidal composition comprises a composition or polymorph of the invention, optionally in combination with an additional biologically active ingredient, or N-oxides or salts thereof, with one or more pharmaceutically or veterinarily acceptable carriers comprising excipients and auxiliaries selected with regard to the intended route of administration (e.g., oral or parenteral administration such as injection) and in accordance with standard practice.
  • a suitable carrier is selected on the basis of compatibility with the one or more active ingredients in the composition, including such considerations as stability relative to pH and moisture content. Therefore of note are compositions and polymorphs of the invention for protecting an animal from an invertebrate parasitic pest comprising a parasitically effective amount of a composition or polymorph of the invention, optionally in combination with an additional biologically active ingredient and at least one carrier.
  • compositions and polymorphs of the invention can be formulated in suspension, solution or emulsion in oily or aqueous vehicles, and may contain adjuncts such as suspending, stabilizing and/or dispersing agents.
  • compositions and polymorphs of the invention may also be formulated for bolus injection or continuous infusion.
  • Pharmaceutical compositions for injection include aqueous solutions of water-soluble forms of active ingredients (e.g., a salt of an active compound), preferably in physiologically compatible buffers containing other excipients or auxiliaries as are known in the art of pharmaceutical formulation. Additionally, suspensions of the active compounds may be prepared in a lipophilic vehicle. Suitable lipophilic vehicles include fatty oils such as sesame oil, synthetic fatty acid esters such as ethyl oleate and triglycerides, or materials such as liposomes.
  • Aqueous injection suspensions may contain substances that increase the viscosity of the suspension, such as sodium carboxymethyl cellulose, sorbitol, or dextran.
  • Formulations for injection may be presented in unit dosage form, e.g., in ampoules or in multi-dose containers.
  • the active ingredient may be in powder form for constitution with a suitable vehicle, e.g., sterile, pyrogen- free water, before use.
  • compositions and polymorphs of the invention may also be formulated as a depot preparation.
  • Such long acting formulations may be administered by implantation (for example, subcutaneously or intramuscularly) or by intramuscular or subcutaneous injection.
  • compositions and polymorphs of the invention may be formulated for this route of administration with suitable polymeric or hydrophobic materials (for instance, in an emulsion with a pharmacologically acceptable oil), with ion exchange resins, or as a sparingly soluble derivative such as, without limitation, a sparingly soluble salt.
  • compositions and polymorphs of the invention can be delivered in the form of an aerosol spray using a pressurized pack or a nebulizer and a suitable propellant, e.g., without limitation, dichlorodifluoromethane,
  • the dosage unit may be controlled by providing a valve to deliver a metered amount.
  • Capsules and cartridges of, for example, gelatin for use in an inhaler or insufflator may be formulated containing a powder mix of the compound and a suitable powder base such as lactose or starch.
  • compositions and polymorphs of the invention may have favourable
  • a composition for protecting an animal from an invertebrate parasite pest in a form for oral administration i.e. comprising, in addition to a parasiticidally effective amount of a composition or polymorph of the invention, one or more carriers selected from binders and fillers suitable for oral administration and feed concentrate carriers).
  • compositions and polymorphs of the invention can be formulated with binders/fillers known in the art to be suitable for oral administration compositions, such as sugars and sugar derivatives (e.g., lactose, sucrose, mannitol, sorbitol), starch (e.g., maize starch, wheat starch, rice starch, potato starch), cellulose and derivatives (e.g., methylcellulose, carboxymethylcellulose,
  • ethylhydroxycellulose ethylhydroxycellulose
  • protein derivatives e.g., zein, gelatin
  • synthetic polymers e.g., polyvinyl alcohol, polyvinylpyrrolidone
  • lubricants e.g., magnesium stearate
  • disintegrating agents e.g., cross-linked polyvinylpyrrolidinone, agar, alginic acid
  • dyes or pigments can be added.
  • Pastes and gels often also contain adhesives (e.g., acacia, alginic acid, bentonite, cellulose, xanthan gum, colloidal magnesium aluminum silicate) to aid in keeping the composition in contact with the oral cavity and not being easily ejected.
  • a composition of the present invention is formulated into a chewable and/or edible product (e.g., a chewable treat or edible tablet).
  • a chewable and/or edible product e.g., a chewable treat or edible tablet.
  • a product would ideally have a taste, texture and/or aroma favored by the animal to be protected so as to facilitate oral administration of the compositions and polymorphs of the invention.
  • the carrier is typically selected from high-performance feed, feed cereals or protein concentrates.
  • feed concentrate-containing compositions can, in addition to the parasiticidal active ingredients, comprise additives promoting animal health or growth, improving quality of meat from animals for slaughter or otherwise useful to animal husbandry.
  • additives can include, for example, vitamins, antibiotics, chemotherapeutics, bacteriostats, fungistats, coccidiostats and hormones.
  • the rate of application required for effective parasitic invertebrate pest control (e.g. "pesticidally effective amount") will depend on such factors as the species of parasitic invertebrate pest to be controlled, the pest's life cycle, life stage, its size, location, time of year, host crop or animal, feeding behavior, mating behavior, ambient moisture, temperature, and the like.
  • One skilled in the art can easily determine the pesticidally effective amount necessary for the desired level of parasitic invertebrate pest control.
  • the compositions and polymorphs of the invention are administered in a pesticidally effective amount to an animal, particularly a homeothermic animal, to be protected from parasitic invertebrate pests.
  • a pesticidally effective amount is the amount of active ingredient needed to achieve an observable effect diminishing the occurrence or activity of the target parasitic invertebrate pest.
  • the pesticidally effective dose can vary for the various compounds and compositions useful for the method of the present invention, the desired pesticidal effect and duration, the target parasitic invertebrate pest species, the animal to be protected, the mode of application and the like, and the amount needed to achieve a particular result can be determined through simple experimentation.
  • a dose of the compositions of the present invention administered at suitable intervals typically ranges from about 0.01 mg/kg to about 100 mg/kg, and preferably from about 0.01 mg/kg to about 30 mg/kg of animal body weight.
  • Suitable intervals for the administration of the compositions of the present invention to animals range from about daily to about yearly. Of note are administration intervals ranging from about weekly to about once every 6 months. Of particular note are monthly adminstration intervals (i.e.
  • the compound of formula Ia(R) was produced using the methods described in WO 2009/080250 and WO 2011/104089. 14mg of this compound in 450 ⁇ 1 of a mixture of 10% water and 90% methanol was placed in a stream of dry nitrogen at 40°C until all the solvent was removed. A mixture of polymorphs was generated.
  • the compound of formula la (racemic mixture) was produced using the methods described in WO 2009/080250. 2g of this compound in 10ml of methanol was subjected to temperature cycling. For the first 1.5 days, the temperature was cycled between room temperature and 40°C every 4 hours with stirring. Stirring was then increased and the upper temperature increased to 50°C and the cycling continued for a further 2 days.
  • the samples were subject to analysis by single crystal X-ray diffraction and/or powder X-ray diffraction.
  • the parameters of the unit cell for polymorph Form 1 and Form 3 are shown in Tables 1 and 2, respectively.
  • the measured 2 ⁇ values of peak positions of the powder X-ray diffraction pattern of the polymorph of Form 2 are shown in Table 3 below.
  • it was possible to calculate the expected powder X-ray diffraction pattern from the single crystals of the polymorphs of Form 1 and Form 3 - this data is also shown in Table 3 below.
  • the 2 ⁇ values are generated or calculated using a wavelength of 1.54056 ⁇ with a 2 ⁇ step size of 0.02°.
  • the polymorphs were further analysed by DSC.
  • the melting points of Form 1, Form 2 and Form 3 are 198°C ⁇ 5°C, 198°C ⁇ 5°C and 185°C ⁇ 5°C, respectively.

Abstract

La présente invention concerne des formes solides de certains insecticides à base de benzamide à substitution isoxazoline, leurs procédés de préparation, des compositions comportant ces formes solides et leurs procédés d'utilisation en tant qu'insecticides, acaricides, nématicides ou molluscicides.
PCT/EP2012/069325 2011-10-03 2012-10-01 Formes polymorphes d'un dérivé d'isoxazoline WO2013050317A1 (fr)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
GBGB1117144.4A GB201117144D0 (en) 2011-10-03 2011-10-03 Polymorphs
GB1117144.4 2011-10-03
EP11190755.6 2011-11-25
EP11190755 2011-11-25
EP11195411 2011-12-22
EP11195411.1 2011-12-22

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WO2014053403A1 (fr) 2012-10-01 2014-04-10 Basf Se Procédé de lutte contre les insectes résistants aux insecticides
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EP4295688A1 (fr) 2022-09-28 2023-12-27 Bayer Aktiengesellschaft Combinaison de composés actifs

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