Polymorphs

Abstract

The present invention relates to solid forms (polymorphs) of insecticides of formula (I), compositions comprising said solid forms and methods of their use as insecticides. (I)

Description

[0001] This application is a divisional application of Chinese Invention Patent Application No. 201880082184.7. Technical Field

[0002] This invention relates to solid forms of isoxazoline derivatives, compositions comprising these solid forms, and methods of using them as insecticides. Background Technology

[0003] WO 2011 / 067272 discloses that certain isoxazoline derivatives possess pest-killing activities, particularly insecticidal, acaricidal, molluscicidal, and nematode-killing activities. Specifically, it discloses a compound having formula I:

[0004] I

[0005] Mixtures of this compound with other insecticides are disclosed in WO 2012 / 163960 and mixtures of this compound with fungicides are disclosed in WO 2012 / 163945. Summary of the Invention

[0006] New solid forms of this compound and its isomers, their compositions, and methods for their preparation and use have now been discovered.

[0007] There are four isomers of the compound having formula I: A, B, C, and D, as shown below. This invention relates to the polycrystalline forms of all these isomers, either in combination or individually.

[0008] (IA) (IB)

[0009] (IC) (ID)

[0010] Therefore, the present invention relates to a novel crystalline form of a compound having formula IA, designated form A(a). This crystalline polymorph form A(a) can be characterized by the unit cell parameters of its single crystal as shown in Table 1. The polymorph was obtained using the method described in Example 1.

[0011] Table 1

[0012] In the table, a, b, c = lengths of the edge of the unit cell; α, β, γ = angles of the unit cell; and Z = molecule / unit cell.

[0013] Therefore, in one embodiment of the invention, the crystalline polymorph named form A(a) has the following lattice parameters: a = 5.06 Å ± 0.01 Å, b = 18.92 Å ± 0.01 Å, c = 24.17 Å ± 0.01 Å, α = 90° ± 0.01°, β = 90° ± 0.01°, γ = 90° ± 0.01°, and volume = 2315 Å. 3 ± 1 Å 3 .

[0014] The crystalline polymorph named form A(a) can also be characterized by a powder X-ray diffraction pattern expressed in terms of 2θ angles or d-intervals. Therefore, in another embodiment of the invention, the crystalline polymorph has a powder X-ray diffraction pattern comprising at least three, at least six, or all of the following group of 2θ angle values: 6.0 ± 0.2, 8.8 ± 0.2, 9.4 ± 0.2, 10.1 ± 0.2, 11.9 ± 0.2, 14.5 ± 0.2, 15.9 ± 0.2, 20.2 ± 0.2, 20.7 ± 0.2, 21.2 ± 0.2, 21.7 ± 0.2, 22.1 ± 0.2, and 22.7 ± 0.2. These peaks, together with the corresponding d-interval values, are shown in Table 2 below: Table 2

[0015] These 2θ angle values ​​were obtained from the powder X-ray diffraction pattern of a polymorph obtained using the method of Example 1. These values ​​were generated using an average wavelength of 1.54056 Å and a 2θ step size of 0.02°.

[0016] In another embodiment, the crystalline polymorph designated as form A(a) has a melting point of 141°C ± 2°C. This melting point was obtained using differential scanning calorimetry (DSC) at a heating rate of 10°C / min.

[0017] Crystalline polymorphs named as form A(a) can also be determined by Raman shift (cm). -1The Raman spectrum expressed by the polymorph is used for characterization. Therefore, in another embodiment of the invention, the crystalline polymorph has a Raman spectrum comprising at least three, at least six, at least nine, at least twelve, at least fifteen, or all Raman shift values ​​selected from the group consisting of: 1698 ± 2, 1640 ± 2, 1603 ± 2, 1564 ± 2, 1458 ± 2, 1364 ± 2, 1293 ± 2, 1272 ± 2, 1201 ± 2, 1178 ± 2, 1092 ± 2, 1069 ± 2, 1011 ± 2, 926 ± 2, 906 ± 2, 876 ± 2, 833 ± 2, 795 ± 2, 752 ± 2, 721 ± 2, 691 ± 2, 658 ± 2, and 631 ± 2.

[0018] This invention also relates to another novel crystalline form of the compound having formula IA, designated form A(b), which can be characterized by a powder X-ray diffraction pattern expressed in 2θ angles or d-intervals. This crystalline polymorph has a powder X-ray diffraction pattern comprising at least three 2θ angle values ​​selected from the group consisting of: 15.3 ± 0.2, 16.3 ± 0.2, 17.6 ± 0.2, 19.3 ± 0.2, 19.8 ± 0.2, 22.0 ± 0.2, 22.9 ± 0.2, 24.9 ± 0.2, and 25.3 ± 0.2. These peaks, together with the corresponding d-interval values, are shown in Table 3 below: Table 3

[0019] These 2θ angle values ​​were obtained from the powder X-ray diffraction pattern of a polymorph obtained using the method of Example 1. These values ​​were generated using an average wavelength of 1.54056 Å and a 2θ step size of 0.02°.

[0020] The crystalline polymorph named form A(b) has a melting point of 152°C ± 2°C. This melting point was obtained using differential scanning calorimetry (DSC) at a heating rate of 10°C / min.

[0021] The present invention also relates to another novel crystalline form of a compound having formula IA that is a hydrate, named form A(h). This crystalline polymorph form A(h) can be characterized by the unit cell parameters of its single crystal as shown in Table 4. The polymorph was obtained using the method described in Example 1.

[0022] Table 4

[0023] In the table, a, b, c = lengths of the edge of the unit cell; α, β, γ = angles of the unit cell; and Z = molecule / unit cell.

[0024] Therefore, in one embodiment of the invention, the crystalline polymorph named form A(h) has the following lattice parameters: a = 8.03 Å ± 0.01 Å, b = 16.10 Å ± 0.01 Å, c = 20.37 Å ± 0.01 Å, α = 90° ± 0.01°, β = 97.02° ± 0.01°, γ = 90° ± 0.01°, and volume = 2615 Å. 3 ± 1 Å 3 .

[0025] The crystalline polymorph named form A(h) can also be characterized by powder X-ray diffraction patterns expressed in terms of 2θ angles or d-intervals. Therefore, in another embodiment of the invention, the crystalline polymorph has a powder X-ray diffraction pattern comprising at least three, at least six, or all of the following group of 2θ angle values: 4.4 ± 0.2, 7.0 ± 0.2, 8.7 ± 0.2, 10.3 ± 0.2, 11.0 ± 0.2, 12.4 ± 0.2, 12.7 ± 0.2, 13.3 ± 0.2, 14.1 ± 0.2, 15.9 ± 0.2, 17.1 ± 0.2, 18.6 ± 0.2, 19.0 ± 0.2, and 19.6 ± 0.2. These peaks, along with the corresponding d-interval values, are shown in Table 5 below: Table 5

[0026] These 2θ angle values ​​were obtained from powder X-ray diffraction patterns predicted using single-crystal intensity data of a polymorph obtained using the method of Example 1. These values ​​were generated using an average wavelength of 1.54056 Å and a 2θ step size of 0.02°.

[0027] The crystalline form of the compound having formula IA is also described, designated as form A(c), which can be characterized by a melting point of 127°C ± 2°C. This melting point was obtained using differential scanning calorimetry (DSC) at a heating rate of 10°C / min. It should be noted that the crystal form of the compound having formula ID will have the same parameters as the crystal form of the compound having formula IA. Therefore, the present invention also relates to novel crystalline forms of the compound having formula ID, which have the physical parameters listed above for the compound having formula IA.

[0028] This invention also relates to a novel crystalline form of a compound having formula IB, which can be characterized by a powder X-ray diffraction pattern expressed in 2θ angles or d-intervals. This crystalline polymorph has a powder X-ray diffraction pattern comprising at least three 2θ angle values ​​selected from the group consisting of: 4.1 ± 0.2, 8.3 ± 0.2, 10.2 ± 0.2, 12.4 ± 0.2, 15.5 ± 0.2, 16.5 ± 0.2, 18.2 ± 0.2, 18.4 ± 0.2, 18.7 ± 0.2, 19.0 ± 0.2, 20.5 ± 0.2, 21.0 ± 0.2, and 21.4 ± 0.2. These peaks, together with the corresponding d-interval values, are shown in Table 6 below: Table 6

[0029] These 2θ angle values ​​were obtained from powder X-ray diffraction patterns predicted using single-crystal intensity data of a polymorph obtained using the method of Example 1. These values ​​were generated using an average wavelength of 1.54056 Å and a 2θ step size of 0.02°.

[0030] The crystalline polymorph of the compound having formula IB has a melting point of 206°C ± 2°C. This melting point was obtained using differential scanning calorimetry (DSC) at a heating rate of 10°C / min.

[0031] This invention also relates to a novel crystalline form of a compound having formula IC, which can be characterized by a powder X-ray diffraction pattern expressed in 2θ angles or d-intervals. This crystalline polymorph has a powder X-ray diffraction pattern comprising at least three 2θ angle values ​​selected from the group consisting of: 4.1 ± 0.2, 8.3 ± 0.2, 10.2 ± 0.2, 12.4 ± 0.2, 15.5 ± 0.2, 16.5 ± 0.2, 18.2 ± 0.2, 18.4 ± 0.2, 18.7 ± 0.2, 19.0 ± 0.2, 20.5 ± 0.2, 21.0 ± 0.2, and 21.4 ± 0.2. These peaks, along with the corresponding d-interval values, are shown in Table 7 below. It should be noted that the powder X-ray diffraction patterns of compounds with formula IC are the same as those of compounds with formula IB.

[0032] Table 7

[0033] These 2θ angle values ​​were obtained from powder X-ray diffraction patterns predicted using single-crystal intensity data of a polymorph obtained using the method of Example 1. These values ​​were generated using an average wavelength of 1.54056 Å and a 2θ step size of 0.02°.

[0034] The crystalline polymorph of the compound having formula IC has a melting point of 206°C ± 2°C. This melting point was obtained using differential scanning calorimetry (DSC) at a heating rate of 10°C / min.

[0035] This invention also relates to another novel crystalline form of the racemic mixture of compounds having formulas IA and ID, which can be characterized by powder X-ray diffraction patterns expressed in 2θ angles or d-intervals. This crystalline polymorph has the following powder X-ray diffraction pattern comprising at least three 2θ angle values ​​selected from the group consisting of: 4.0 ± 0.2, 8.1 ± 0.2, 9.7 ± 0.2, 11.1 ± 0.2, 12.7 ± 0.2, 15.3 ± 0.2, 15.9 ± 0.2, 16.2 ± 0.2, 16.7 ± 0.2, 18.4 ± 0.2, 19.5 ± 0.2, 19.8 ± 0.2, 20.3 ± 0.2, 21.8 ± 0.2, and 23.9 ± 0.2. These peaks, together with the corresponding d-interval values, are shown in Table 8 below: Table 8

[0036] These 2θ angle values ​​were obtained from the powder X-ray diffraction pattern of a polymorph obtained using the method of Example 1. These values ​​were generated using an average wavelength of 1.54056 Å and a 2θ step size of 0.02°.

[0037] The crystalline polymorphs of the racemic forms of the compounds having formulas IA and ID have a melting point of 173°C ± 2°C. This melting point was obtained using differential scanning calorimetry (DSC) at a heating rate of 10°C / min.

[0038] In the context of this invention, a polymorph is a specific 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 comprises constituent molecules arranged in a sequential repeating pattern extending in three-dimensional space (in contrast, amorphous solid forms do not exhibit long-range regularity in molecular positioning). Different polymorphs of a compound have different atomic and / or molecular arrangements in their crystal structures. When the compound is a bioactive compound such as an insecticide, differences in crystal structure can lead to different polymorphs with different chemical, physical, and biological properties. Properties that can be affected include crystal morphology, density, hardness, color, chemical stability, melting point, water absorption, suspension rate, dissolution rate, and bioavailability. Thus, a particular polymorph can possess properties that make it more advantageous in practical use compared to another polymorph of the same compound: specifically, the physical, chemical, and biological properties listed above can significantly influence the production methods and formulation development of plant treatments (such as insecticides), the ease with which the compound can be combined with other active ingredients and formulation components, and its quality and efficacy. It should be noted that it is impossible to predict whether a compound will exist in a solid state as more than one polymorph, nor is it possible to predict the properties of any of these polymorphs.

[0039] Specifically, using a specific polymorph can allow for the use of novel formulations compared to the presence of a compound in a polycrystalline / amorphous form. This can be advantageous for many reasons. For example, suspension concentrate (SC) formulations may be preferred over emulsion concentrate (EC) formulations because the lack of solvent in SCs generally means that the formulation may have lower phytotoxicity than an equivalent EC formulation—however, if the form in which the compound is present is unstable in such an SC formulation, polymorphic transformations may occur, leading to undesirable crystal growth. Such crystal growth is detrimental because it leads to, for example, thickening and potential solidification of the formulation, which can cause clogging of application equipment (e.g., spray nozzles) in agricultural application machinery. Using a stable polymorphic form will overcome these problems.

[0040] The solid phase can be determined in the presence of crystals using conventional methods known in the art. For example, powder X-ray diffraction is convenient and routine. Other techniques that can be used include differential scanning calorimetry (DSC), thermogravimetric analysis (TGA), and Raman or infrared spectroscopy, NMR, gas chromatography, or HPLC. Single-crystal X-ray diffraction is particularly useful in identifying crystal structures.

[0041] The polymorphs of the present invention can be applied in their unchanged form, but are more preferably applied by means of incorporation into agricultural chemical compositions. Therefore, in another aspect, the present invention provides an agricultural chemical composition comprising the polymorphs of the present invention as defined above, and at least one agriculturally acceptable carrier or diluent.

[0042] Furthermore, the compositions of the present invention may comprise more than one polymorph of the present invention. In particular, compounds having formula IA are more bioactive than compounds having formulas IB, IC, and ID. Thus, although the compositions of the present invention may contain the polymorphs disclosed herein or mixtures of compounds of formulas IA, IB, IC, and ID in any other amount, they may also be enriched with compounds having formula IA or polymorphs of compounds having formula IA. In particular, they may be enriched into polymorphs named form A(a). "Enriched" means that the molar proportion of compounds or polymorphs having formula IA is greater than 50% compared to the total amount of compounds having formulas IA, IB, IC, and ID, for example at least 55%, 60%, 65%, 70%, 75%, 80%, 85%, 90%, 95%, 96%, 97%, 98%, or at least 99%.

[0043] Agricultural chemical compositions comprising one or more polymorphs of the present invention are active ingredients with preventative and / or therapeutic value in the field of pest control. Even at low application rates, they exhibit a favorable biocidal spectrum and are well tolerated by warm-blooded species, fish, and plants. The compositions of the present invention can act on all or only individual developmental stages of normally susceptible and resistant animal pests (such as insects or representatives of mites). The insecticidal or acaricidal activity of these compositions can be directly manifested, i.e., for example, destruction of pests during molting, which occurs immediately or only after a period of time; or indirectly manifested, for example, reduced oviposition and / or hatching rates, with good activity corresponding to a destruction rate (mortality rate) of at least 50%-60%.

[0044] Thus, agricultural chemical compositions comprising one or more polymorphs of the present invention can be used to control plant pathogenic insects on a variety of plant species. Therefore, the present invention also provides a method for preventing / controlling insect infestations on plants or plant propagation material, the method comprising treating the plant or plant propagation material with an insecticidal amount of the agricultural composition of the present invention.

[0045] As used herein, the term "insecticide" means a compound or composition that controls or alters the growth of insects. The term "effective insecticide amount" refers to the amount of a compound or composition, or a combination or composition of such compounds, that is capable of killing, controlling or infecting insects, delaying the growth or reproduction of insects, reducing insect populations and / or reducing insect-induced plant damage.

[0046] "Plant propagation material" refers to all kinds of seeds (fruits, tubers, bulbs, grains, etc.), cuttings, felling branches, etc.

[0047] Examples of the aforementioned animal pests are: From the order Acari, including species of the genera *Acalitus*, *Aculus*, *Acaricalus*, *Aceria*, *Acarussiro*, *Amblyomma*, *Argas*, *Boophilus*, *Brevipalpus*, *Bryobia*, *Calipitrimerus*, *Chorioptes*, *Dermanyssus gallinae*, *Dermatophagoides*, and *Eotetranychus*. Species of the genera *Eriophyes*, *Hemitarsonemus*, *Hyalomma*, *Ixodes*, *Olygonychus*, *Ornithodoros*, *Polyphagotarsone latus*, *Panonychus*, *Phyllocoptruta oleivora*, *Phytonemus*, *Polyphagotarsonemus*, *Psoroptes*, *Rhipicephalus*, and *Rhizoglyphus*. spp.), species of the genus Sarcoptes spp., species of the genus Steneotarsonemus spp., species of the genus Tarsonemus spp., and species of the genus Tetranychus spp.; From the order Lobelia, such as species of the genera Haematopinus spp., Linognathus spp., Pediculus spp., Pemphigus spp., and Phylloxera spp.; From the order Coleoptera, such as species of the genera *Agriotes* spp., *Amphimallonmajale*, *Anomala orientalis*, *Anthonomus* spp., *Aphodius* spp., *Astylus atromaculatus*, *Ataenius* spp., *Atomaria linearis*, *Chaetocnema tibialis*, *Cerotoma* spp., *Conoderus* spp., *Cosmopolites* spp., *Cotinis nitida*, *Curculio* spp., *Cyclocephala* spp., and *Dermestes*. Species of the genera *Diabrotica* (spp.), *Diloboderus abderus*, *Epilachnas* (spp.), *Eremnus* (spp.), *Heteronychus arator*, *Hypothenemushampei*, *Lagria vilosa*, *Leptinotarsa ​​decemLineata*, *Lissorhoptrus* (spp.), *Liogenys*, *Maecolaspis*, *Maladeracastanea*, *Megascelis* (spp.), *Melighetes aeneus*, *Melolontha* (spp.), *Myochrous armatus*, *Orycaephilus* (spp.), and *Otiorhynchus* (spp.). Species of the genera *Phyllophaga*, *Phlyctinus*, *Popillia*, *Psylliodes*, *Rhyssomatus aubtilis*, *Rhizopertha*, Scarabidae, and *Sitophilus*.), species of the genera *Sitotroga*, *Somaticus*, *Sternechus subsignatus*, *Tenebrio*, *Tribolium*, and *Trogoderma*. From the order Diptera, such as species of the genera *Aedes*, *Anopheles*, *Antherigona soccata*, *Bactrocea oleae*, *Bibiohortulanus*, *Bradysia*, *Calliphora erythrocephala*, *Ceratitis*, *Chrysomyia*, *Culex*, *Cuterebra*, *Dacus*, *Delia*, *Drosophila melanogaster*, *Fannias*, *Gastrophilus*, and *Geomyza*. *Tripunctata*, *Glossina* spp., *Hypoderma* spp., *Hyppobosca* spp., *Liriomyza* spp., *Lucilia* spp., *Melanagromyza* spp., *Musca* spp., *Oestrus* spp., *Orseolia* spp., *Oscinella frit*, *Pegomyia hyoscyami*, *Phorbia* spp., *Rhagoletis* spp., *Rivelia quadrifasciata*, *Scatella* species, *Sciara* spp., *Stomoxys* spp., *Tabanus* species spp.), species of the genus *Tannia* spp., and species of the genus *Tipula* spp.; From the order Hemiptera, such as *Acanthocoris scabrator*, species of *Acrosternum*, *Adelphocoris lineolatus*, *Bathycoelia thalassina*, species of *Clavigralla*, species of *Creontiades*, *Dichelops furcatus*, species of *Edessa*, species of *Euchistus*, *Eurydemapulchrum*, species of *Pseudomonas*, *Tea-winged*, and *Horcias*. *Nobilellus*, *Rhizophora*, *Nesidiocoris*, *Nesidiocoris tenuis*, *Nesidiocoris*, *Nesidiocoris simulans*, *Nesidiocoris*, *Nesidiocoris*, *Nesidiocoris simulans*, *Nesidiocoris*, *Nesidiocoris*, *Nesidiocoris*, *Nesidiocoris*, *Nesidiocoris castanea ... From the order Hemiptera, such as the pea aphid (Acyrthosium pisum), species of the genus *Adalges*, *Agalliana ensigera*, *Talgilon psyllid*, species of the genus *Aleurodicus*, species of the genus *Aleurocanthus*, sugarcane whitefly, soft-haired whitefly (Aleurothrixus floccosus), cabbage whitefly (Aleyrodes brassicae), cotton leafhopper (Amarasca biguttula), lemon leafhopper, species of the genus *Aonidiella*, golden orange kidney scale (Aonidiella auranti), aphids, species of the genus *Aspidiotus*, *Acyrthosium pisum*, potato psyllid (Bactericera cockerelli), species of the genus *A.*, and species of the genus *Brachycaudus*. spp.), cabbage aphid, species of the genus *Cavariella* aegopodii Scop., species of the genus *Cavariella*, black-brown round shield scale, orange-brown round shield scale, species of the genus *Cofana*, species of the genus *Cofana*, species of the genus *Cryptospira*, species of the genus *C.*, brown soft scale, yellow-winged corn leafhopper, species of the genus *Gymnocypris*, citrus psyllid, wheat double-tailed aphid, species of the genus *C.*, species of the genus *C.*, woolly apple aphid, species of the genus *C.*, species of the genus *Gascardia*, *Glycaspis brimblecombei*, *Hyadaphis pseudobrassicae*, species of the genus *Hyalopterus* spp., and species of the genus *Hyperomyzus* *Pallidus*, *Idioscopusclypealis*, *African leafhopper*, *Grey planthopper* species, *Soil scale*, *Oyster scale* species, *Lopaphiserysimi*, *Lyogenys maidis*, *Long-tubed aphid* species, *Froghopper* species, *Metcalfa pruinosa*, *Wheat leafhopper*, *Wheat waxhopper*, *Gallworm* species, *Neotoxoptera sp.*, *Black-tailed leafhopper* species, *Nilaparvata spp.*), Pear Green Aphid, Odonaspis ruthae, Sugarcane Cotton Aphid, Myrica Marginata Whitefly, Cox's Psyllid, Species of the genus *Pseudatomoscelis*, Species of the genus *Gallus*, Corn Lanternfly, Species of the genus *Phylloxera*, Species of the genus *Phylloxera*, Species of the genus *Pseudatomoscelis*, Species of the genus *Pulvinaria*, Species of the genus *Pulvinaria*, Species of the genus *Quesada gigas*, Species of the genus *Recilia dorsalis*, Species of the genus *Pseudatomoscelis*, Species of the genus *Pulvinaria*, Species of the genus *Pulvinaria*, Species of the genus *Pleurotus*, Species of the genus *Pseudatomoscelis*, Species of the genus *Pulvinaria*, Species of the genus *Pulvinaria*, Species of the genus *Pleurotus*, Species of the genus *Pulvinaria ... Proserpina), species of the genus *Proserpina*, species of the genus *Tridiscus* sporoboli, species of the genus *Trionymus* spp., African psyllids, arrowhead scales, flame leafhoppers, and *Zyginidia scutellaris*. From the order Hymenoptera, such as species of the genera *Acromyrmex*, *Arge* spp., *Atta* spp., *Cephus* spp., *Diprion* spp., Diprionidae, *Gilpinia polytoma*, *Hoplocampa* spp., *Lasius* spp., *Monomorium pharaonis*, *Neodiprion* spp., *Pogonomyrmex* spp., *Solenopsis* spp., and *Vespa* spp.; From the order Isoptera, such as species of the genera *Coptotermes spp.*, *Corniternes cumulans*, *Incisitermes spp.*, *Macrotermes spp.*, *Mastotermes spp.*, *Microtermes spp.*, and *Reticulitermes spp.*; tropical fire ants (*Solenopsis geminate*). From the order Lepidoptera, such as species of the genera *Longwinged Roller*, *Brown-banded Roller*, *Clearwing Moth*, *Noctuid Moth*, cotton leafhopper, *Amylois*, *Lysimachia*, *Yellow Roller*, *Argyresthia spp.*, *Betweenlea*, *Spodoptera*, cotton leafminer, corn leafminer, powdery leafminer, peach fruit borer, *Grass borer*, *Leaf Roller*, *Chrysoteuchia topiaria*, grape fruit borer, *Leaf Roller*, *Cloud Roller*, *Striped Roller*, *Shellworm*, and Lepidoptera butterflies, *Cosmophila*. *Flava* species, *Catharanthus* species, *Catharanthus macrocarpa*, *Catharanthus spp.*, *Catharanthus* species, *Catharanthus spp.* ... *Bifidalis*, species of the genera *Bombyx moth*, *Minter moth*, *Ephemeral leafminer*, *Cabbage moth*, *Tobacco hawk moth*, species of the genera *Mythimna*, *Minter moth*, *Geometrid moth*, *Orniodes indica*, *European corn borer*, species of the genera *Small leafroller*, *Brown leafroller*, *Small-eyed leafroller*, *Stem borer*, *Pectinophoragos sypiela*, *Coffee leafminer*, *Armor borer*, *Potato leafminer*, *Cabbage white butterfly*, species of the genera *Cabbage white butterfly*, *Cabbage white butterfly*, species of the genera *Prunella vulgaris*, species of the genera *Geometrid moth*, *Peppermint leafroller*, *Richia albicosta*, species of the genera *Scirpophaga spp.*, species of the genera *Stem borer*, species of the genera *Long-haired leafroller*, species of the genera *Grey-winged leafroller*, *Cotton leafroller*, species of the genera *Heteropterus*, species of the genera *Lepidoptera*, *Powdered leafroller*, *Tomato leafminer*, and species of the genera *Ophiopogon*. From the order Trichophagida, for example, species of the genera *Leptococcus* and *Leptococcus*; From the order Orthoptera, such as species of the genera *Berberis*, *Berberis*, *Molecus*, *Madeira*, *Migratory Locust*, *Neocurtilla hexadactyla*, *Berberis*, *Scapteriscus spp*, and *Desert Locust*. From the order Psittaciformes, such as species of the genus *Liposcelis*. From the order Siphonaptera, such as species of the genera *Ceratophyllus*, *Ctenocephalides*, and *Xenopsylla cheopis*. From the order Thysanoptera, such as *Calliothrips phaseoli*, species of the genera *Frankliniella*, *Heliothrips*, *Hercinothrips*, *Parthenothrips*, *Scirtothrips aurantii*, *Sericothrips variabilis*, species of the genera *Taeniothrips*, and species of the genera *Thrips*; and / or From the order Thysanura, such as silverfish (Lepisma saccharina).

[0048] Examples of soil-dwelling pests that can damage crops in the early stages of plant development include: From the order Lepidoptera, such as species of the genera *Acleris*, *Aegeria*, *Agrotis*, *Alabama argillaceae*, *Amylois*, *Autographa*, *Busseola fusca*, *Cadra cautella*, *Chilo*, *Crocidolomiabinotalis*, *Diatraea*, *Diparopsis castanea*, *Elasmopalpus*, *Heliothis*, *Mamestra brassicae*, and *Phthorimaea*. operculella, diamondback moth (Plutellaxylostella), species of the genera Scirpophaga spp., species of the genera Sesamia spp., species of the genera Spodoptera spp., and species of the genera Tortrix spp.; From the order Coleoptera, for example, species of the genera *Agriotes*, *Anthonomus*, *Atomaria linearis*, *Chaetocnematibialis*, *Conotrachelus*, *Cosmopolites*, *Curculio*, *Dermestes*, *Diabroticas*, *Dilopoderus*, *Epilachna*, *Eremnus*, *Heteronychus*, *Lissorhoptrus*, *Melolontha*, and *Orycaephilus*. spp.), species of the genera *Otiorhynchus*, *Phlyctinus*, *Popillia*, *Psylliodes*, *Rhizopertha*, Scarabidae, species of the genera *Sitotroga*, *Somaticus*, *Tanymecus*, *Tenebrio*, *Tribolium*, *Trogoderma*, and *Zabrus*; From the order Orthoptera, such as species of the genus *Gryllotalpa*. From the order Isoptera, such as species of the genus *Reticulitermes*; From the order Psittaciformes, such as species of the genus *Liposcelis*. From the order Lobelia, such as species of the genera Haematopinus spp., Linognathus spp., Pediculus spp., Pemphigus spp., and Phylloxera spp.; From the order Hemiptera, such as the apple cotton aphid (Eriosoma larigerum); From the order Hymenoptera, for example, species of the genera *Topleaf-cutter*, *Butterleaf-cutter*, *Stemleaf-flyer*, *Hairy ant*, *Yellow ant*, *New pine leaf-flyer*, *Fire ant*, and *Vespa*. From the order Diptera, such as species of the genus Tipula spp.; Cruciferous plants including flea beetles (species of the genus *Phyllotreta*), root maggots (species of the genus *Delia*), cabbage leaf weevils (species of the genus *Ceutorhynchus*), and aphids.

[0049] The compositions of the present invention can also be used to control nematodes. Thus, agricultural chemical compositions comprising the polymorphs of the present invention can be used to control plant pathogenic nematodes on a variety of plant species. Therefore, the present invention also provides a method for controlling damage to plants or parts thereof caused by plant-parasitic nematodes (endoparasitic, semi-endoparasitic, and ectoparasitic nematodes), the method comprising treating the plant or plant propagation material with a nematicidal amount of the agricultural composition of the present invention.

[0050] As used herein, the term "nematicide" means a compound or composition that controls or alters the growth of nematodes. The term "nematicidal effective amount" means an amount of a compound or composition, or a combination of such compounds or compositions, that is capable of killing, controlling or infecting nematodes, inhibiting their growth or reproduction, reducing their population, and / or reducing damage to plants caused by nematodes.

[0051] Examples of plant-parasitic nematodes mentioned above are: Root-knot nematodes, *Meloidogyne hapla* (northern root-knot nematode), *Meloidogyne incognita* (southern root-knot nematode), *Meloidogyne javanica* (Java root-knot nematode), *Meloidogyne arenaria* (peanut root-knot nematode), and other root-knot nematode species; cyst-forming nematodes, *Globodera rostochiensis* (potato golden nematode), and other *Globodera* species; *Heterodera avenae* (grass cyst nematode), *Heteroderaglycines* (soybean cyst nematode), *Heterodera schachtii* (beet cyst nematode), *Heterodera trifolii* (red clover heterodermatitis), and other *Heterodera* species; seed gall nematodes, *Anguina* species; stem and leaf nematodes (Stem and... Species of the genera *Folium foliarum* and *Aphelenchoides*; species of *Sting nematode*, *Eelonolaimus longicaudatus*, and other species of the genera *Belonolaimus*; species of *Pine nematodes*, *Bursaphelenchus xylophilus*, and other species of the genera *Bursaphelenchus*; species of *Ring nematodes*, *Criconema*, *Criconemella*, *Criconemoides*, and *Mesocriconema*; species of *Stemand bulb nematodes*, *Ditylenchus destructor*, *Ditylenchus dipsaci*, and other species of the genera *Ditylenchus*; and species of *Awl*. Species of the genus *Helicotylenchus*, *Spiral nematodes*, *Heliocotylenchus multicinctus*, and other species of the genus *Helicotylenchus*.Species of the genera *Hemicycliophora* and *Hemicriconemoides*; species of the genus *Hirshmanniella*; species of the genus *Lancenematodes* and *Hoploaimus*; species of the genus *False rootknot nematodes* and *Nacobbus*; species of the genus *Needle nematodes*, *Longidoruselongatus*, and other *Longidorus*; species of the genus *Pin nematodes* and *Pratylenchus*; nematodes of the genus *Lesion*, *Pratylenchusneglectus*, and *Pratylenchus*. * *Pratylenchus penetrans*, *Pratylenchus curvitatus*, *Pratylenchus goodeyi*, and other species of the genus *Pratylenchus*; *Burrowing nematodes*, *Radopholus similis*, and other species of the genus *Radopholus*; *Reniform nematodes*, *Rotylenchus robustus*, *Rotylenchus reniformis*, and other species of the genus *Rotylenchus*; species of the genus *Scutellonema*; *Stubby root nematodes*, *Trichodorus*, and other species of the genus *Trichodorus*. primitivus) and other species of the genus *Trichodorus* and *Paratrichodorus*; Stuntnematodes, Tylenchorhynchus claytoni, Tylenchorhynchus dubius and other species of the genus *Tylenchorhynchus*; Citrus nematodes and Tylenchulus species;Species of the genus *Dagger nematodes* and *Xiphinema*; and other plant-parasitic nematode species, such as species of the genera *Subanguinas*, *Hypsoperine*, *Macroposthonia*, *Melinius*, *Punctodera*, and *Quinisulcius*.

[0052] In particular, these nematode species can be controlled by the compositions of the present invention: species of the genera *Root-knot Nematodes*, *Heteroderm*, *Cyclophorus*, and *Brief-bodied Nematodes*.

[0053] The compositions according to the invention can be used to control, i.e., to contain or destroy pests of the types described above, which are particularly found on plants, especially useful and ornamental plants in agriculture, horticulture and forestry, or on the organs of these plants, such as fruits, flowers, leaves, stems, tubers or roots, and in some cases, even plant organs formed at a later point in time remain protected against these pests.

[0054] Suitable target crops are, in particular, cereals such as wheat, barley, rye, oats, rice, corn, or sorghum; sugar beets such as sugar beets or fodder beets; fruits such as pome, stone fruits, or seedless small fruits such as apples, pears, plums, peaches, apricots, cherries, or berries such as strawberries, raspberries, or blackberries; legumes such as beans, lentils, peas, or soybeans; and oil crops such as rapeseed, mustard, poppies, olives, sunflowers, coconuts, castor beans, cocoa beans, or peanuts. Cucurbit crops, such as pumpkins, cucumbers, or melons; fiber plants, such as cotton, flax, hemp, or jute; citrus fruits, such as oranges, lemons, grapefruits, or tangerines; vegetables, such as spinach, lettuce, asparagus, cabbage, carrots, onions, tomatoes, potatoes, or bell peppers; Lauraceae, such as avocados, cinnamon, or camphor; and also tobacco, nuts, coffee, eggplants, sugarcane, tea, pepper, grapevines, hops, plantains, and latex plants.

[0055] The compositions and / or methods of the present invention can also be used on any ornamental plants and / or vegetable crops (including flowers, shrubs, broad-leaved trees and evergreens).

[0056] For example, this invention can be used for any of the following ornamental plant species: *Ageratum* species, *Alonsoa* species, *Anemone* species, *Heliotropium* species, *Chrysanthemum* species, *Snapdragon* species, *Aster* species, *Begonia* species (e.g., *Begonia riegerii*, *Begonia semperflorens*, *Begonia tubéreux*), *Bougainvillea* species, *Brachycome* species, *Brachycome* species (ornamental plants), *Pueraria* species, pepper, periwinkle, *Canna* species, *Cornflower* species, *Chrysanthemum* species, *Cinnamomum* species, *Coreopsis* species, *Crassula coccinea*, *Cuphea ignea*, *Dahlia* species, *Delphinium* species, bleeding heart, *Dorotheantus* species, *Lisianthus* species, *Forsythia* species, *Fuchsia* species, *Geranium* gnaphalium), species of the genera *Gnaphalium*, *Globe amaranth*, species of the genera *Heliotropium*, species of the genera *Heliotropium*, species of the genera *Hibiscus*, species of the genera *Hydrangea*, species of the genera *Hydrangea*, species of the genera *Euphorbia*, species of the genera *Iresines spp.*, species of the genera *Kalanchoe*, *Lantana*, *Hemerocallis fulva*, species of the genera *Lilium*, species of the genera *Physalis*, species of the genera *Physalis*, species of the genera *Mentha*, species of the genera *Phyllanthus*, species of the genera *Marigold*, species of the genera *Carnation*, species of the genera *Canna*, species of the genera *Oxalis*, species of the genera *Daisy*, species of the genera *Pelargonium* (Pelargonium peltatum, Pelargonium spp.), species of the genera *Viola* (Viola tricolor), species of the genera *Petunia*, species of the genera *Oleander*, species of the genera *Plecthranthus* spp.), species of the genera *Poinsettia*, *Parthenocissus* (including five-leafed Parthenocissus and Virginia creeper), species of the genera *Primula*, *Rhododendron*, species of the genera *Rosa*, species of the genera *Datura*, species of the genera *Viola*, species of the genera *Salvia*, *Scaevola aemola*, *Schizanthus wisetonensis*, species of the genera *Sedum*, species of the genera *Solanum*, species of the genera *Surfinia*, species of the genera *Marigold*, species of the genera *Nicotiana*, species of the genera *Verbena*, species of the genera *Zinnia*, and other bedding plants.

[0057] For example, this invention can be used for any of the following vegetable species: Allium species (garlic, onion, A. oschaninii, leek, shallot, scallion), fennel, celery (Apium graveolus), asparagus, beet (Beta vulgarus), Brassica species (cabbage, Chinese cabbage, turnip), chili pepper, chickpea, endive, chicory species (chicory, endive), watermelon (Citrillus lanatus), cucumber species (cucumber, melon), squash species (zucchini, squash), artichoke species (Cyanaraspp.) (artichoke, spiny artichoke), wild carrot, fennel, St. John's wort species, lettuce, tomato species (tomato, cherry tomato), mint species, basil, parsley, common bean species (bean, green bean), pea, radish, edible rhubarb, rosemary species, sage species, black ginseng (Scorzonera) Hispanica), eggplant, spinach, species of the genus *Vallisneria* (Vallisneria eriocarpa), and broad beans.

[0058] Preferred ornamental plant species include African violet, Begonia, Dahlia, Sedum, Hydrangea, Verbena, Rosa, Kalanchoe, Poinsettia, Aster, Cornflower, Coreopsis, Delphinium, Mentha, Oleander, Yellow Daisy, Sedum, Petunia, Viola, Impatiens, Geranium, Chrysanthemum, Ranunculus, Fuchsia, Sage, Hydrangea, Rosemary, Sage, St. John's Wort, Mint, Sweet Pepper, Tomato, and Cucumber.

[0059] The polymorphs of the present invention are particularly suitable for controlling bean aphids (Aphis craccivora), cucumber leaf beetles (Diabrotica balteata), tobacco shoot cutworms (Heliothisvirescens), peach aphids (Myzus persicae), diamondback moths (Plutella xylostella), and sea spodoptera littoralis on cotton, vegetables, corn, rice, and soybean crops. The polymorphs of the present invention are also particularly suitable for controlling Mamestra (preferably on vegetables), codling moths (preferably on apples), leafhoppers (preferably in vegetables and vineyards), leaf beetles (Leptinotarsa) (preferably on potatoes), and rice stem borers (Chilo supressalis) (preferably on rice).

[0060] Crops should be understood as those that exist naturally, are obtained through conventional breeding methods, or are obtained through genetic engineering. These include crops that possess so-called output traits (such as improved storage stability, higher nutritional value, and improved flavor).

[0061] Crops should be understood to also include those crops that have been conferred tolerance to herbicides (like bromonazine) or multiple classes of herbicides (such as ALS-, EPSPS-, GS-, HPPD-, and PPO- inhibitors). An example of a crop that has been conferred tolerance to imidazolinones (e.g., methoxyfenozide) through conventional breeding methods is Clearfield® Summer Canola. Examples of crops conferred herbicide tolerance through genetic engineering methods include, for example, glyphosate and glufosinate-resistant maize varieties, which are commercially available under the brand names RoundupReady®, Herculex I®, and LibertyLink®.

[0062] Crops should also be understood as those that are naturally or have been conferred resistance to pests. This includes plants that, for example, are capable of synthesizing one or more selectively acting toxins through the use of recombinant DNA technology, such toxins being derived from toxin-producing bacteria. Examples of toxins that can be expressed include delta-endotoxins, vegetative insecticidal proteins (Vip), insecticidal proteins from bacterial colonizing nematodes, and toxins produced by scorpions, arachnids, wasps, and fungi.

[0063] An example of a crop modified to express Bacillus thuringiensis toxin is Bt maize KnockOut® (Syngenta Seeds). An example of a crop that encodes insecticidal resistance and thus expresses more than one gene for more than one toxin is VipCot® (Syngenta Seeds). Crops or their seed material can also be resistant to multiple types of pests (a so-called superimposed transgenic event when produced through genetic modification). For example, plants can express insecticidal proteins while also being resistant to herbicides, such as Herculex I® (Dow AgroSciences, Pioneer Hi-Bred International).

[0064] Other applications of the compositions according to the invention include protecting stored articles and storage rooms, as well as protecting raw materials such as timber, textiles, flooring, or buildings, and also in the field of hygiene, particularly protecting humans, livestock, and productive animals from pests of the types mentioned.

[0065] The present invention also provides a method for controlling pests (such as mosquitoes and other disease vectors; see also http: / / www.who.int / malaria / vector_control / irs / en / ). In one embodiment, the method for controlling pests includes applying the composition of the present invention to the target pests, their location, or a surface or substrate by brushing, rolling, spraying, coating, or impregnation. By way of example, the method of the present invention is contemplated for application of IRS (Indoor Residual Spray) to surfaces (such as wall, ceiling, or floor surfaces). In another embodiment, the application of such compositions to substrates such as nonwoven or fabric materials in the form of netting, coverings, bedding, curtains, and tents (or which can be used in the manufacture of these articles) is contemplated. A further object of the present invention is therefore a matrix selected from nonwoven and fabric materials comprising compositions containing compounds having formula (I).

[0066] In one embodiment, a method for controlling such pests includes applying a biocidally effective amount of the composition of the invention to the target pests, their location, or a surface or substrate to provide effective residual biocidal activity on said surface or substrate. Such application can be carried out by brushing, rolling, spraying, coating, or impregnating the biocidal composition of the invention. By way of example, the method of the invention is considered for IRS application to surfaces (such as wall, ceiling, or floor surfaces) to provide effective residual biocidal activity on said surfaces. In another embodiment, the application of such a composition for residual pest control on a substrate, such as a fabric material in the form of a net, cover, quilt, curtain, or tent (or which may be used in the manufacture of these articles), is considered.

[0067] The substrate to be treated (including nonwovens, fabrics, or meshes) can be made of natural fibers such as cotton, raffia leaf fibers, jute, flax, sisal, burlap, or wool, or synthetic fibers such as polyamide, polyester, polypropylene, polyacrylonitrile, etc. Polyester is particularly suitable. Methods for treating textiles are known, for example, WO 2008 / 151984, WO2003 / 034823, US 5631072, WO 2005 / 64072, WO 2006 / 128870, EP 1724392, WO 2005113886, or WO 2007 / 090739.

[0068] Another application of the compositions according to the invention is in the field of tree injection / trunk treatment for all ornamental trees, as well as all kinds of fruit and nut trees.

[0069] In the field of tree injection / trunk treatment, the polymorphs according to the present invention are particularly suitable for combating wood-boring insects from the Lepidoptera and Coleoptera mentioned above, especially those listed in Tables A and B below: Table A. Examples of economically important invasive wood-boring insects.

[0070]

[0071] Table B. Examples of local wood-boring insects of economic importance.

[0072]

[0073] This invention can also be used to control any insect pests that can exist in lawn grass, including, for example, beetles, caterpillars, fire ants, ground pearls, millipedes, sowbugs, mites, mole crickets, scale insects, mealybugs, froghoppers, southern wheat bugs, and grubs. This invention can be used to control insect pests at all stages of their life cycle, including eggs, larvae, nymphs, and adults.

[0074] Specifically, this invention can be used to control insect pests fed on the roots of lawn grasses, including grubs (such as species of the genus *Cyclocephala* spp., e.g., the marked scarab beetle, *C. lurida*), species of the genus *Rhizotrogus* (e.g., the European scarab beetle, *R. majalis*), species of the genus *Cotinus* (e.g., the green June beetle, *C. nitida*), species of the genus *Popillia* spp. (e.g., the Japanese beetle, *P. japonica*), species of the genus *Phyllophaga* spp. (e.g., the May / June beetle), species of the genus *Ataenius* (e.g., the Black turfgrass ataenius, *A. spretulus*), and species of the genus *Maladera* spp. (e.g., the Asiatic garden beetle, *M.*). castanea and species of the genus Tomarus), ground pearl (species of the genus Margarodes spp.), mole crickets (brownish-yellow, southern, and short-winged; species of the genus Scapteriscus spp., and African mole cricket (Gryllotalpa africana)), and leafjackets (European cranefly, species of the genus Tipula spp.).

[0075] This invention can also be used to control insect pests in lawn grasses of thatched houses, including armyworms (such as the fall armyworm Spodoptera frugiperda and the common armyworm Pseudaletia unipuncta), root cutters, weevils (species of the genus Sphenophorus, such as S. venatus verstitus and S. parvulus), and grass moths (such as species of the genus Crambus and the tropical grass moth Herpetogramma phaeopteralis).

[0076] This invention can also be used to control insect pests in turfgrass that live on the ground and feed on the leaves of turfgrass. These insect pests include wheat bugs (such as southern wheat bugs and southern stem bugs (Blissus insularis)), bermudagrass mite (Eriophyes cynodoniensis), grass mealybug (Antonina graminis)), two-lined grasshopper (Propsapia bicincta), leafhoppers, root-cutting moths (Noctuidae), and wheat aphids.

[0077] This invention can also be used to control other harmful organisms in lawn grass, such as introduced red imported fire ants (Solenopsis invicta) that create nests in lawns.

[0078] In the field of hygiene, the compositions according to the invention are effective against ectoparasites such as hard ticks, soft ticks, scabies mites, fall mites, flies (biting and licking), parasitic fly larvae, lice, hair lice, bird lice and fleas.

[0079] Examples of this type of parasite are: Lice: species of the genera *Haematopinus*, *Linognathus*, *Pediculus*, *Phtirus*, and *Solenopotes*.

[0080] Trichophagia: Species of the genera *Trimenopon*, *Menopon*, *Trinoton*, *Bovicola*, *Werneckiella*, *Lepikentron*, *Damalina*, *Trichodectes*, and *Felicola*.

[0081] Diptera and the suborders Nematocerina and Brachycerina, such as species of the genera *Aedes*, *Anopheles*, *Culex*, *Simulium*, *Eusimulium*, *Phlebotomus*, *Lutzomyia*, *Culicoides*, *Chrysops*, *Hybomitra*, *Atylotus*, *Tabanus*, and *Haematopota*. Species of the genera *Philipomyia*, *Braulaspp.*, *Musca*, *Hydrotaea*, *Stomoxys*, *Haematobia*, *Morellia*, *Fannia*, *Glossina*, *Calliphora*, *Lucilia*, *Chrysomyia*, *Wohlfahrtia*, *Sarcophaga*, *Oestrus*, *Hypodermas*, and *Gasterophilus*. spp.), species of the genus *Hippobosca*, species of the genus *Lipoptena*, and species of the genus *Melophagus*.

[0082] Siphonapterida, including species of the genera *Pulex*, *Ctenocephalides*, *Xenopsylla*, and *Ceratophyllus*.

[0083] Heteropterida, including species of the genera *Cimex*, *Triatoma*, *Rhodnius*, and *Panstrongylus*.

[0084] Blattodea, including species such as the Oriental cockroach (Blatta orientalis), the American cockroach (Periplaneta americana), the German cockroach (Blattelagermanica), and species of the genus Supella (Supella spp.).

[0085] Acaria (subclass Acaria, family Acarida), and the orders Meta-stigmata and Meso-stigmata, including species of the genera *Argas*, *Ornithodorus*, *Otobius*, *Ixodes*, *Amblyommas*, *Boophilus*, *Dermacentor*, *Haemophysalis*, *Hyalomma*, *Rhipicephalus*, *Dermanyssus*, *Raillietia*, and *Pneumonyssus*. spp.), species of the genus *Sternostoma* spp., and species of the genus *Varroaspp.*.

[0086] Actinedida (prostigmata) and Acaridida (Astigmata), including species of the genera *Acarapis*, *Cheyletiella*, *Ornithocheyletia*, *Myobia*, *Psorergates*, *Demodex*, *Trombicula*, *Listrophorus*, *Acarus*, *Tyrophagus*, *Caloglyphus*, *Hypodectes*, and *Pterolichus*. Species of the genera *Psoroptes*, *Chorioptes*, *Otodectes*, *Sarcoptes*, *Notoedress*, *Knemidocoptes*, *Cytodites*, and *Laminosioptes*.

[0087] The compositions according to the invention are also suitable for protecting materials such as wood, textiles, plastics, adhesives, glues, paints, paper and cards, leather, flooring and buildings from insect infestation.

[0088] The compositions according to the invention can be used, for example, to combat the following pests: beetles such as the North American house longhorn beetle (Hylotrupes bajulus), the long-haired longhorn beetle (Chlorophorus pilosis), the furniture thief (Anobium punctatum), the red-haired thief (Xestobium rufovillosum), the comb-horned thief (Ptilinuspecticornis), the dendrobium pertinex, the pine bud thief (Ernobius mollis), the primed carpini, the brown powder beetle (Lyctus brunneus), the African powder beetle (Lyctus africanus), the southern powder beetle (Lyctus planicollis), the oak powder beetle (Lyctus linearis), the pubescens powder beetle (Lyctus pubescens), and the breast powder beetle (Trogoxylon). The species include *Aequale*, *Minthesrugicollis*, species of *Xyleborus* spec., species of *Tryptodendron* spec., *Apate monachus*, *Bostrychus capucins*, *Heterobostrychus brunneus*, species of *Sinoxylon* spec., and *Dinoderus minutus*, as well as hymenopterans such as *Sirex juvencus*, *Urocerus gigas*, *Urocerus gigas taignus*, and *Urocerus augu*, and termites such as *Kalotermes flavicollis*, *Cryptotermes brevis*, and *Heterotermes*. The termites include *Indicola*, *Reticulitermes flavipes*, *Reticulitermes santonensis*, *Reticulitermes lucifugus*, *Mastotermes darwiniensis*, *Zootermopsis nevadensis*, and *Coptotermes formosanus*, as well as wood-boring insects such as silverfish (*Lepisma saccharina*).

[0089] The application rate of the agrochemical compositions of the present invention depends on the specific type of insects to be controlled, the required level of control, and the timing and method of application, and can be readily determined by those skilled in the art. Generally, the compositions of the present invention can be applied at a rate between 0.005 kg / ha and about 5.0 kg / ha, based on the total amount of the active ingredient (wherein 'active ingredient' means one or more polymorphs of the present invention). An application rate between about 0.1 kg / ha and about 1.5 kg / ha is preferred, and an application rate between about 0.3 kg / ha and 0.8 kg / ha is particularly preferred.

[0090] In practice, agrochemical compositions containing one or more polymorphs of the present invention are applied as formulations containing a variety of adjuvants and carriers known or used in industry.

[0091] These formulations may be in various physical forms, such as powders, gels, wettable powders, water-dispersible granules, water-dispersible tablets, effervescent compressed tablets, emulsifiable concentrates, microemulsifiable concentrates, oil-in-water emulsions, flowable oils, aqueous dispersions, oily dispersions, suspensions, capsule suspensions, emulsifiable granules, soluble liquids, water-soluble concentrates (using water or water-miscible organic solvents as a carrier), impregnated polymer films, or other known forms, such as those described in the Manual on Development and Use of FAO and WHO Specifications for Pesticides, United Nations, 1st Edition, Second Revision (2010). Such formulations may be used directly or diluted prior to use. They may be diluted with, for example, water, liquid fertilizers, micronutrients, biological organisms, oils, or solvents.

[0092] The formulation can be prepared, for example, by mixing one or more polymorphs ('active ingredient') with a formulation adjuvant to obtain a formulation in the form of a finely dispersed solid, particles, solution, dispersion, or emulsion. The active ingredient can also be formulated with other adjuvants, such as finely dispersed solids, mineral oils, plant or animal-derived oils, modified plant or animal-derived oils, organic solvents, water, surfactants, or combinations thereof.

[0093] The active ingredient can also be contained in very fine microcapsules. The microcapsules contain the active ingredient within a porous carrier. This allows the active ingredient to be released into the environment in a controlled amount (e.g., slow release). Microcapsules typically have a diameter from 0.1 to 500 micrometers. They contain an amount of active ingredient ranging from about 25% to 95% by weight of the capsule. The active ingredient can be in the form of a bulk solid, fine particles in a solid or liquid dispersion, or in a suitable solution. The encapsulating membrane can comprise, for example, natural or synthetic rubber, cellulose, styrene / butadiene copolymers, polyacrylonitrile, polyacrylates, polyesters, polyamides, polyureas, polyurethanes, or chemically modified polymers, as well as starch xanthates, or other polymers known to those skilled in the art. Alternatively, very fine microcapsules can be formed in which the active ingredient is contained in the form of finely dispersed particles within a solid matrix of a base substance, but these microcapsules themselves are not encapsulated.

[0094] The adjuvants used in the preparation of formulations according to the present invention are known in themselves. As liquid carriers, the following can be used: water, toluene, xylene, petroleum ether, vegetable oil, acetone, methyl ethyl ketone, cyclohexanone, acid anhydride, acetonitrile, acetophenone, amyl acetate, 2-butanone, butylene carbonate, chlorobenzene, cyclohexane, cyclohexanol, alkyl acetate, diacetone alcohol, 1,2-dichloropropane, diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycol, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, N,N-dimethyl... Formamide, dimethyl sulfoxide, 1,4-dioxane, dipropylene glycol, dipropylene glycol methyl ether, dipropylene glycol dibenzoate, dipropylene glycol, alkylpyrrolidone, ethyl acetate, 2-ethylhexanol, ethylene carbonate, 1,1,1-trichloroethane, 2-heptanone, α-pinene, d-limonene, ethyl lactate, ethylene glycol, ethylene glycol butyl ether, ethylene glycol methyl ether, γ-butyrolactone, glycerol, glyceryl acetate, glyceryl diacetate, glyceryl triacetate, deca-acetate, etc. Hexadecane, hexanediol, isopentyl acetate, isobornyl acetate, isooctane, isophorone, cumene, isopropyl myristate, lactic acid, laurylamine, isopropyl acetone, methoxypropanol, methyl isopentyl ketone, methyl isobutyl ketone, methyl lauryl ketone, methyl octanoate, methyl oleate, dichloromethane, m-xylene, n-hexane, n-octylamine, octadecanoic acid, octylamine acetate, oleic acid, oleyleneamine, o-xylene, phenol, polyethylene glycol, propionic acid, propyl lactate Propylene carbonate, propylene glycol, propylene glycol methyl ether, p-xylene, toluene, triethyl phosphate, triethylene glycol, xylenesulfonic acid, paraffin, mineral oil, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, propylene glycol methyl ether, diethylene glycol methyl ether, methanol, ethanol, isopropanol, and alcohols with higher molecular weights, such as pentanol, tetrahydrofuranol, hexanol, octanol, ethylene glycol, propylene glycol, glycerol, N-methyl-2-pyrrolidone, etc.

[0095] Suitable solid carriers include, for example, talc, titanium dioxide, pyrophyllite clay, silica, attapulgite clay, diatomaceous earth, limestone, calcium carbonate, bentonite, calcium montmorillonite, cottonseed hulls, wheat flour, soybean flour, pumice, wood flour, walnut shell powder, lignin, and similar substances.

[0096] Many surfactants can be advantageously used in both solid and liquid formulations, especially those that can be diluted with a carrier before use. Surfactants can be anionic, cationic, nonionic, or polymeric, and they can be used as emulsifiers, wetting agents, suspending agents, or for other purposes. Typical surfactants include, for example, salts of alkyl sulfates, such as diethanolammonium dodecyl sulfate; salts of alkyl aryl sulfonates, such as calcium dodecylbenzenesulfonate; alkylphenol / olefin oxide addition products, such as nonylphenol ethoxylate; alcohol / olefin oxide addition products, such as tridecyl alcohol ethoxylate; soaps, such as sodium stearate; salts of alkyl naphthalene sulfonates, such as sodium dibutylnaphthalene sulfonate; dialkyl esters of sulfosuccinates, such as sodium di(2-ethylhexyl)sulfosuccinate; sorbitol esters, such as sorbitol oleate; quaternary ammonium compounds, such as dodecyltrimethylammonium chloride; polyethylene glycol esters of fatty acids, such as polyethylene glycol stearate; block copolymers of ethylene oxide and propylene oxide; and salts of monoalkyl and dialkyl phosphate esters; and those described in, for example, McCutcheon's Detergents and Emulsifiers Annual, MC Publishing Corp., Ridgewood New Jersey. Other substances in Richwood, New Jersey (1981).

[0097] Other adjuvants that can be used in formulations for killing pests include crystallization inhibitors, viscosity modifiers, suspending agents, dyes, antioxidants, foaming agents, light absorbers, mixing aids, defoamers, complexing agents, substances that neutralize or change pH and buffer solutions, corrosion inhibitors, fragrances, wetting agents, absorption enhancers, micronutrients, plasticizers, flow aids, lubricants, dispersants, thickeners, antifreeze agents, microbial agents, and liquid and solid fertilizers.

[0098] Formulations according to the invention may include additives comprising oils of plant or animal origin, mineral oils, alkyl esters of such oils, or mixtures of such oils and oil derivatives. The amount of oil additive in the formulations according to the invention is typically from 0.01% to 10% of the mixture to be applied. For example, the oil additive may be added to the spray can at the desired concentration after the spray mixture has been prepared. Preferred oil additives include mineral oils or plant-derived oils, such as rapeseed oil, olive oil, or sunflower oil; emulsified vegetable oils; alkyl esters of plant-derived oils, such as methyl derivatives; or animal-derived oils, such as fish oil or tallow. Preferred oil additives include C8-C... 22 Alkyl esters of fatty acids, especially C 12 -C 18 Methyl derivatives of fatty acids, such as lauric acid, palmitic acid, and methyl esters of oleic acid (methyl laurate, methyl palmitate, and methyl oleate, respectively). Many oil derivatives are known from the Compendium of Herbicide Adjuvants, 10th edition, Southern Illinois University, 2010.

[0099] The formulations of the present invention generally comprise from 0.1% to 99%, particularly from 0.1% to 95% by weight, the polymorph of the present invention, and from 1% to 99.9% by weight, a formulation adjuvant, which preferably comprises from 0% to 25% by weight of a surfactant. Commercial products may preferably be formulated as concentrates, while end users will typically use diluted formulations.

[0100] Application rates vary over a wide range and depend on soil properties, application method, crop species, pests to be controlled, primary climatic conditions, and other factors governed by application method, application time, and target crop. Generally, the polymorph of the present invention can be applied at rates from 1 to 2000 l / ha, particularly from 10 to 1000 l / ha.

[0101] Preferred formulations may have the following composition (by weight%): Emulsifiable concentrates:

[0102] Dust agent:

[0103] Suspension concentrate:

[0104] Wettable powder:

[0105] Granules:

[0106] The following examples further illustrate (but do not limit) the invention.

[0107]

[0108] The combination is thoroughly mixed with an adjuvant and the mixture is thoroughly ground in a suitable grinder to obtain a wettable powder that can be diluted with water to give a suspension of the desired concentration.

[0109]

[0110] The combination is thoroughly mixed with the adjuvant and the mixture is thoroughly ground in a suitable grinder to obtain a powder that can be used directly for seed treatment.

[0111]

[0112] Emulsions with any required dilution that can be used in plant protection can be obtained by diluting such concentrates with water.

[0113]

[0114] A ready-to-use dust is obtained by mixing the aforementioned combination with a carrier and grinding the mixture in a suitable grinder. Such powders can also be used for dry seed dressing.

[0115]

[0116] The mixture is combined with an adjuvant and ground, and the mixture is moistened with water. The mixture is extruded and then dried in an air stream.

[0117]

[0118] This finely ground mixture is applied evenly to kaolin moistened with polyethylene glycol in a mixer. This process yields dust-free coated granules.

[0119] suspension concentrate

[0120] The finely ground combination is tightly mixed with an adjuvant to obtain a suspension concentrate, from which a suspension concentrate can be diluted with water to obtain a suspension of any desired dilution. Using such a dilution, living plants along with their propagation material can be treated and protected against microbial infection by spraying, watering, or immersion.

[0121] Flowable concentrate for seed treatment

[0122] The finely ground combination is tightly mixed with an adjuvant to obtain a suspension concentrate, from which a suspension concentrate can be diluted with water to obtain a suspension of any desired dilution. Using such a dilution, living plants along with their propagation material can be treated and protected against microbial infection by spraying, watering, or immersion.

[0123] Sustained-release capsule suspension

[0124] 28 parts of the active ingredient were mixed with 2 parts of an aromatic solvent and 7 parts of a toluene diisocyanate / polymethylene-polyphenyl isocyanate mixture (8:1). This mixture was emulsified in a mixture of 1.2 parts of polyvinyl alcohol, 0.05 parts of an antifoaming agent, and 51.6 parts of water until the desired particle size was achieved. 2.8 parts of a mixture of 1,6-hexanediamine and 5.3 parts of water were added to this emulsion. The mixture was stirred until polymerization was complete. The resulting capsule suspension was stabilized by adding 0.25 parts of a thickener and 3 parts of a dispersant. The capsule suspension formulation contained 28% of the active ingredient. The diameter of the medium-sized capsules was 8-15 micrometers. The resulting formulation was applied to seeds as an aqueous suspension suitable for this application.

[0125] Each of the above formulations can be prepared as a package containing one or more polymorphs of the present invention along with other components of the formulation (diluents, emulsifiers, surfactants, etc.). The formulations can also be prepared by a barrel mixing method, wherein the components are obtained individually and combined at the growth site.

[0126] These formulations can be applied to the desired controlled area using conventional methods. For example, powder and liquid formulations can be applied using powered dusters, nozzle sprayers, manual sprayers, and spray dusters. The formulations can also be applied from aircraft as dust or spray, or via rope cores. Both solid and liquid formulations can be applied to the soil at the plant site to be treated, allowing the active ingredients to penetrate the plants through root penetration.

[0127] The polymorphs and compositions thereof of the present invention are also applicable to the protection of plant propagation materials (e.g., seeds, fruits, tubers, or grains, or nursery plants) against pests of the aforementioned types. The propagation material can be treated with the polymorphs before planting, for example, seeds can be treated before sowing. Alternatively, the polymorphs can be applied to the seed grains (coating), which is achieved by immersing the grains in a liquid composition or by applying a layer of solid composition. The composition may also be applied while the propagation material is being planted at the application site, for example, by applying the composition to the seed furrows during row sowing. These methods of treating plant propagation material and the plant propagation material thus treated are further subjects of the present invention. Typical treatment ratios will depend on the plant to be controlled and the pest / fungus, and are generally between 1 gram and 200 grams per 100 kg of seeds, preferably between 5 grams and 150 grams per 100 kg of seeds, such as between 10 grams and 100 grams per 100 kg of seeds.

[0128] The term seed includes all kinds of seeds and plant propagules, including but not limited to true seeds, seed masses, suckers, grains, bulbs, fruits, tubers, cereals, rhizomes, cuttings, cut branches and the like, and in a preferred embodiment means true seeds.

[0129] The present invention also includes seeds coated or treated with or containing the polymorphs of the present invention. Although more or less of the component may penetrate into the seed material depending on the method of application, the term "coated or treated and / or containing" generally indicates that, at the time of application, the active ingredient is, in most cases, on the surface of the seed. When the seed product is (re)planted, it can absorb the active ingredient. In embodiments, the present invention makes it possible to obtain plant propagation material having a compound of formula (I) adhered thereto. Furthermore, compositions comprising plant propagation material treated with a compound of formula (I) are thus obtained.

[0130] Seed treatment includes all suitable seed treatment techniques known in the art, such as seed dressing, seed coating, seed dusting, seed soaking, and seed granulation. The application of a compound having formula (I) for seed treatment can be achieved by any known method, such as spraying or dusting before or during sowing / planting.

[0131] Suitablely, the agrochemical compositions and formulations of the present invention are applied before disease occurs. The application rate and frequency of these formulations are common in the art and depend on the risk of insect pathogen infection.

[0132] By including other active substances, the activity of compositions comprising compounds and polymorphs according to the invention can be significantly broadened and adapted to the prevailing environment. These active substances can be chemical or biological in nature, and, in terms of biological type, can be further modified from naturally derived biological varieties. Active substances generally include substances that control, repel, or attract harmful organisms that damage or harm useful plants, and also include substances that improve the growth of useful plants (such as plant growth regulators), as well as substances that improve the performance of the active substances (such as synergists). Examples are insecticides, acaricides, nematicides, molluscicides, algaecides, virus inhibitors, rodenticides, bactericides, fungicides, chemical sterilizers, and anthelmintics. Examples of bioactive substances include baculoviruses, plant extracts, and bacteria.

[0133] Therefore, the present invention provides for use of the compositions according to the invention in conjunction with one or more pesticides, phytonutrients, or plant fertilizers. The compositions may also include specific plant traits incorporated into plants using any means, such as conventional breeding or genetic modification.

[0134] The polymorphs of the present invention, when mixed with other active substances, can also have further, unexpected advantages, which can be described more broadly as synergistic activity. For example, better plant tolerance, reduced phytotoxicity, controlled insect behavior at different developmental stages, or improved behavior related to production (e.g., grinding or mixing, storage, or use).

[0135] Independent active substances can appear in more than one group or species, and in more than one position within one group or species: information on active substances, their spectrum, sources and classifications can be found in the Compendium of Pesticide Common Names (see http: / / www.alanwood.net / pesticides / index.html) or in the Pesticide Manual created by the British Crop Production Counci (see http: / / bcpcdata.com / pesticide-manual.html).

[0136] Preferred mixtures are shown below, wherein one or more polymorphs of the present invention are indicated by "I": Compositions containing adjuvants include I+ compounds selected from the group consisting of substances derived from petroleum.

[0137] Compositions containing acaricides include I + 1,1-bis(4-chlorophenyl)-2-ethoxyethanol, I + 2,4-dichlorophenylbenzenesulfonate, I + 2-fluoro-N-methyl-N-1-naphthylacetamide, I + 4-chlorophenylphenyl sulfone, I + abamectin, I + mitoxin, I + acetamiprid, I + flufenoxuron, I + aldicarb, I + α-cypermethrin, I + cypermethrin, I + sulfadiazine, I + aminothiocyanate, I + phosmet, I + phosmet oxalate, I + amitraz, I + dicofol, I + arsenic trioxide, I + AVI 382, ​​I + AZ 60541, I + fenpropathrin, I + azinphos-methyl, I + azobenzene, I + azacyclotin, I + Azothoate, I+ Benoxafos, I+ Benoxafos, I+ Benzoximate, I+ Benzyl benzoate, I+ Bifenazate, I+ Cypermethrin, I+ Acaricide, I+ Bromocypermethrin, I+ Bromocyclen, I+ Bromothion, I+ Ethyl Bromothion, I+ Bromopropylate, I+ Thiazidone, I+ Butylpyridaben, I+ Butylpyridaben, I+ Calcium polysulfide, I+ Campheechlor, I+ Carbanolate, I+ Carnavallar, I+ Carbofuran, I+ Carbothion, I+ CGA 50' 439, I+ Chinomethionat, I + chlorbenside, I + amitraz, I + amitraz hydrochloride, I + bromonitrile, I + chlorfenson, I + chlorfensulfide, I + chlorfenphos, I + chlorobenzilate, I + chloromebuform, I + chloromethiuron, I + chloropropylate, I + chlorpyrifos, I + methyl chlorpyrifos, I + chlorthiophos, I + cinerin I, I + cinerins, I + tetradifon, I + chlorpyrifos, I+ Coumarin, I + Cromiton, I + Crotoxyphos, I + Thiazol, I + Cyanthoate, I + Fenflurfen, I + Trichlorofluorocarbons, I + Tricyclic Tin, I + Cypermethrin, I + DCPM, I + DDT, I + Demephion, I + Demephion-O, I + Demeton-S, I + Methyl Demeton, I + Demeton-O, I + Methyl Demeton-O, I + Demeton-S, I + Methyl Demeton-S, I + Demeton-S-methylsulfonon, I + Acaricide, I + Dialifos, I + Diazinon, I + Benzylsulfonamide, I + Dichlorvos, I + Diclophos, I+ chlorpyrifos, I+ chlorpyrifos, I+ dimethoate, I+ dinactin, I+ dinex, I+ dinex-diclexine, I+ dinobuton, I+ dinocap, I+ dinocap-4, I+ dinocap-6, I+ dinitrate, I+ dinopenton, I+ dinosulfon, I+ dinoterbon, I+ dioxazine, I+ diphenyl sulfone, I+ disulfiram, I+ ethion, I+ DNOC, I+ dofenapyn, I+ dofenapyn, I+ endothion, I+ EPN, I+ Ilinoxetine, I + ethion, I + ethoate-methyl, I + etoxazole, I + etrimfos, I + fenazaflor, I + quinfenoxam, I + fenbutatin oxide, I + fenothiocarb, I + cypermethrin, I + fenpyrad, I + fenpyroximate, I + fenson, I + fentrifanil, I + cypermethrin, I + fipronil, I + fluacrypyrim, I + fluzolon, I + flubenzimine, I + flufenoxuron, I +Flucythrinate, I + fluenetil, I + flufenoxuron, I + flumethrin, I + fluorbenside, I + fluvalinate, I + FMC1137, I + amitraz, I + amitraz hydrochloride, I + formothion, I + formoparanate, I + γ-HCH, I + glyodine, I + halfenprox, I + heptenophos, I + hexadecylcyclopropane carboxylate, I + thiamethoxam, I + iodomethane, I + isocarbophos, I + isopropyl O-(methoxyaminothiophosphoryl)salicylate, I + ivermectin, I + Jasmolin I, I + Jasmolin II, I + Jodfenphos, I + Lindane, I + Lufenuron, I + Malathion, I + Malonoben, I + Mecarbam, I + Mephosfolan, I + Thiophanate, I + Methacrifos, I + Methamidophos, I + Phosphate, I + Dimethoate, I + Methyl bromide, I + Metelcarb, I + Mexacarb, I + Mexacarb, I + Milbemycin Oxime, I + Mipafox, I + Phosphate, I + Morothion, I + Moxifloxacin, I + Dibromophos (naled), I+ NC-184, I+ NC-512, I+ nifluridide, I+ nicotinic acid, I+ nitrilacarb, I+ nitrilacarb 1:1 zinc chloride complex, I+ NNI-0101, I+ NNI-0250, I+ omethoate, I+ chlorpyrifos, I+ oxydeprofos, I+ oxydisulfoton, I+ pp'-DDT, I+ parathion, I+ permethrin, I+ petroleum, I+ fenthion, I+ phorate, I+ methamidophos, I+ phosfolan, I+ imidacloprid, I+Phosphine, I + Phoxim, I + Methylpyrimidine, I + Polychloroterpenes, I + Polynactins, I + Prochloraz, I + Probromophos, I + Promacyl, I + Acaricide, I + Proetamphos, I + Prothidathion, I + Prothoate, I + Pyrethrin I, I + Pyrethrin II, I + Pyrethrins, I + Pyridaphenthion, I + Pyrimidifen, I + Pyrimidathion, I + Quinalphos, I + Quintiofos, I + R-1492, I + RA-17, I + Rotenone, I + Schradan, I + sebufos, I + selamectin, I + SI-0009, I + sophamide, I + fenpyroxene, I + spirodiclofen, I + SSI-121, I + sulfluramid, I + sulfotep, I + sulfur, I + SZI-121, I + t-flufenoxuron, I + pyridaben, I + TEPP, I + terbam, I + stiorophos, I + tetradifon, I + tetraactin, I + tetrasul, I + thiafenox, I + thiocarboxime, I + thiofanox, I + Thiometon, I + Acaricide, I + Thuringiensin, I + Triamiphos, I + Triarathene, I + Triazophos, I + Triazophos, I + Trifenofos, I + Trifenactin, I + Phoxim, I + Vaniliprole, and I + YI-5302.

[0138] Compositions containing anthelmintics include: I+ abamectin, I+ clofentylamide, I+ doxorubicin, I+ imacodyl, I+ imacodyl benzoate, I+ irinotecan, I+ ivermectin, I+ milbemycin, I+ moxicritin, I+ piperazine, I+ selamectin, I+ spinosad, and I+ thiophanate.

[0139] Compositions containing bird toxicants include: I+ chloralose, I+ isodrin, I+ fenthion, I+ pyridine-4-amine and I+ strychnine.

[0140] Compositions containing biocontrol agents include: I+ *Adoxophyes oranaGV*, I+ *Agrobacterium radiata*, I+ *Amblyseius spp.*, I+ *Anagrapha falcifera* NPV, I+ *Anagrus atomus*, I+ *Aphelinus abdominalis*, I+ *Aphidius colemani*, I+ *Aphidoletes aphidimyza*, I+ *Autographa californica* NPV, I+ *Bacillus firmus*, I+ *Bacillus sphaericus Neide*, I+ *Bacillus thuringiensis* Berliner, I+ Bacillus thuringiensis subsp. aizawai, I+ Bacillus thuringiensis subsp. israelensis, I+ Bacillus thuringiensis subsp. japonensis, I+ Bacillus thuringiensis subsp. kurstaki, I+ Bacillus thuringiensis subsp. t.tenebrionis), I + Beauveria bassiana, I + Beauveria brongniartii, I + Chrysoperla carnea, I + Cryptolaemus montrouzieri, I + Cydia pomonella Gv, I + Dacnusa sibirica, I + Diglyphus isaea, I + Encarsia formosa, I + Eretmocerus eremicus, I + Helicoverpa zea NPV, I + Heterorhabditis bacteriophora, and H. megidis, I+ convergent ladybug (Hippodamia convergens), I+ citrus scale insect parasitic wasp (Leptomastix dactylopii), I+ mirid bug (Macrolophus caliginosus), I+ cabbage noctuid moth nucleopolyhedrovirus (Mamestra brassicae NPV), I+ Metaphycus helvolus, I+ Metarhizium anisopliae var. acridum, I+ Metarhizium anisopliae var. anisopliae, I+ Neodiprion sertifer nucleopolyhedrovirus, and red-headed pine leaf beetle (N.Lecontei) nucleopolyhedrovirus, I+ species of the genus *Lecontei*, I+ *Paecilomyces fumosoroseus*, I+ *Phytoseiulus persimilis*, I+ *Spodoptera exigua multicapsid* multinucleate capsid nucleopolyhedrovirus, I+ *Steinernema bibionis*, I+ *Steinernema carpocapsae*, I+ *Steinernema glaseri*, I+ *Steinernema riobrave*, I+ *Steinernema riobravis*, I+ *Steinernema scapterisci*, I+ species of the genus *Steinernema*, I+ species of the genus *Trichogramma*, I+ *Typhlodromus occidentalis*, and I+ Verticillium lecanii.

[0141] Compositions containing soil disinfectants include: I + iodomethane and methyl bromide.

[0142] Compositions containing chemical sterilizing agents include: I+ azirphosphazine, I+ bisazir, I+ busulfan, I+ diflubenzuron, I+ dimatif, I+ hexamethylmelamine, I+ hexamethylphosphine, I+ methyl thiophanate, I+ thiothiophanate, I+ methyl apholate, I+ morzid, I+ flufenoxuron, I+ tepa, I+ thiohempa, I+ thiothiophanate, I+ tratamine, and I+ urethaneimine.

[0143] Compositions containing insect pheromones include: I+(E)-dec-5-en-1-yl acetate and (E)-dec-5-en-1-ol, I+(E)-tetrate-4-en-1-yl acetate, I+(E)-6-methylhept-2-en-4-ol, I+(E,Z)-tetradec-4,10-dien-1-yl acetate, I+(Z)-dodec-7-en-1-yl acetate, I+(Z)-hexadec-11-enal, I+(Z)-hexadec-11-en-1-yl acetate, I+(Z)-hexadec-13-en-11-yn-1-yl acetate, I+(Z)-eicoseno-13-en-10-one, I+(Z)-tetradec-7-en-1-al, I+(Z)-tetradec-9-en-1-ol, I+(Z)-decane-9-en-1-ol, I+(Z)-decane-5-en-1-yl acetate, I+(Z)-decane-5-en-1-ol, I+(Z)-decane-5-en-1-yl acetate, I+(Z)-decane-5-en-1-yl acetate, I+(Z)-decane-5-en-1-yl acetate, I+(Z)-decane-5-en-1-yl acetate, I+(Z)-decane-5-en-1-ol ... +(Z)-Tetradecano-9-en-1-yl acetate, I + (7E,9Z)-Dodeca-7,9-dien-1-yl acetate, I + (9Z,11E)-Tetradecano-9,11-dien-1-yl acetate, I + (9Z,12E)-Tetradecano-9,12-Dien-1-yl acetate, I + 14-methyloctadecyl-1-ene, I + 4-methylnonanal-5-ol and 4-methylnonanal-5-one, I + α-multistriatin, I + brevicomin (a pheromone associated with the western pine bark beetle), I + codlelure, I + codlemone, I + cuelure, I + disparlure, I + dodec-8-en-1-yl acetate, I + dodec-9-en-1-yl acetate, I + dodec-8, I + 10-dien-1-yl acetate, I + dominicalure, I + ethyl 4-methyloctanoate, I + eugenol, I + frontalin (a pheromone associated with the southern pine bark beetle), I + gossyplure, I + Grandlure, I + Grandlure I, I + Grandlure II, I + Grandlure III, I + Grandlure IV, I + Hexalure, I + Ipsdienol, I + Ipssenol, I + Japonilure, I + Lineatin, I + Litlure, I + Looplure, I + Medlure, I + Megatomoic acid, I + Methyl eugenol, I + Muscalure, I + Octadec-2,13-dien-1-yl acetate, I + Octadec-3,13-dien-1-yl acetate, I + Orfralure, I+oryctalure, I+ostramone, I+siglure, I+sordidin, I+sulcatol, I+tetradecanoate-11-en-1-ylacetate, I+teradone, I+teradone A, I+teradone B1, I+teradone B2, I+teradone C, and I+trunc-call.

[0144] Compositions containing insect repellents include: I + 2-(octylthio)ethanol, I + butopyronoxyl, I + butoxy (polypropylene glycol), I + dibutyl adipate, I + dibutyl phthalate, I + dibutyl succinate, I + DEET, I + dimethyl carbate, I + dimethyl phthalate, I + ethylhexanediol, I + hexamethylenetetramine, I + methoquin-butyl, I + methylneodecanamide, I + oxamate, and I + hydroxypiperate.

[0145] Compositions containing insecticides include I+ 1-dichloro-1-nitroethane, I+ 1,1-dichloro-2,2-di(4-ethylphenyl)ethane, I+, I+ 1,2-dichloropropane, I+ 1,2-dichloropropane and 1,3-dichloropropene, I+ 1-bromo-2-chloroethane, I+ 2,2,2-trichloro-1-(3,4-dichlorophenyl)ethyl acetate, I+ 2,2-dichlorovinyl-2-ethylsulfinylethylmethyl phosphate, I+ 2-(1,3-dithiacyclopentan-2-yl)phenyl dimethylcarbamate, I+ 2-(2-butoxyethoxy)ethyl thiocyanate, I+ 2-(4,5-dimethyl-1,3-dioxolane-2-yl)phenyl methylcarbamate, I+ 2-(4-chloro-3,5-dimethyloxy)ethanol, I + 2-chlorovinyldiethyl phosphate, I + 2-imidazolinone, I + 2-isovalerylindan-1,3-dione, I + 2-methyl(prop-2-ynyl)aminophenyl methylcarbamate, I + 2-thiocyanoethyl laurate, I + 3-bromo-1-chloroprop-1-ene, I + 3-methyl-1-phenylpyrazol-5-yl dimethylcarbamate, I + 4-methyl(prop-2-ynyl)amino-3,5-dimethylyl dimethylcarbamate, I + 5,5-dimethyl-3-oxocyclohexyl-1-enyl dimethylcarbamate, I + abamectin, I + acephate, I + acetamiprid, I + acetamiprid, I + flufenoxuron, I + acrylonitrile, I + Cottonseed oil, I + aldicarb, I + aldicarb, I + chlorpyrifos, I + allethrin, I + aprofen, I + chlorpyrifos, I + α-cypermethrin, I + α-ecdysone, I + aluminum phosphide, I + cypermethrin, I + thioamide, I + chlorpyrifos, I + amethiocarb, I + amethiocarb oxalate, I + amitraz, I + neonicotinoids, I + ethyl phosmet, I + AVI 382, ​​I + AZ 60541, I + azadirachtin, I + methylpyridinium phosphate, I + ethyl glutathione, I + methyl glutathione, I + azophos, I + Bacillus thuringiensis δ-endotoxins, I + barium hexafluorosilicate, I + barium polysulfide, I + fenvalerate, I + Bayer 22 / 190, I + Bayer 22408, I + Imamectin, I + Carbofuran, I + Cypermethrin, I + β-Cypermethrin, I + β-Cypermethrin, I + Bifenthrin, I + Bio-Allethrin, I + Bio-Allethrin S-Cypermethrin Isomer, I + Bioethanomethrin, I + Bio-Cypermethrin, I +Pyrethroids, I + di(2-chloroethyl) ether, I + bis(triflufenoxam), I + borax, I + bromopyrethrin, I + bromophenylenephos, I + bromochlor, I + bromo-DDT, I + bromothion, I + bromothion-ethyl, I + carbaryl, I + thiamethoxam, I + chlorpyrifos, I + butathiofos, I + methyl ethyl ketone, I + butyl phosphate, I + methyl ethyl ketone sulfonate, I + butylpyridinium chloride, I + thionyl phosphate, I + calcium arsenate, I + calcium cyanide, I + calcium polysulfide, I + toxaphene, I + chlorpyrifos, I + carbaryl, I + carbofuran, I + carbon disulfide, I + carbon tetrachloride, I + trithionyl phosphate, I + thiophanate-methyl, I + fenitrothion, I + pyrethroid hydrochloride, I + silvastatin, I + borneol, I + chlordane, I + chlorfenapyr, I + amitraz, I + amitraz hydrochloride, I + oxychlorpyrifos, I + brofenoxuron, I + chlorfenapyr, I + difenoconazole, I + chlormethoate, I + chloroform, I + trichloronitromethane, I + chlorpyrifos, I + pyridaben, I + chlorpyrifos-methyl, I + chlorfenapyr, I + cyclophosphamide, I + pyrimethanil I, I + pyrimethanil II, I + pyrimethanil derivatives, I + cis-resmethrin, I + cismethrin, I + cypermethrin, I + fenpropathrin, I + chlorfenapyr, I + thiamethoxam, I + Copper acetylated arsenite, I + copper arsenate, I + copper oleate, I + phosmet, I + phosmet, I + clomiphene, I + phosmet, I + chlorpyrifos, I + cryolite, I + CS 708, I + benzoylphos, I + pyrethroid, I + cypermethrin, I + cypermethrin, I + deltamethrin, I + cypermethrin, I + cypermethrin, I + cypermethrin, I + cypermethrin, I + cypermethrin, I + cyclomethrin, I + phosmet, I + d-limonene, I + d-tetramethrin, I + DAEP, I + dazomet, I + DDT, I + decarbofuran, I + deltamethrin, I + phosmet-O, ​​I + phosmet-S, I + Systemic phosphorus, I + systemic phosphorus-methyl, I + systemic phosphorus-O, I + systemic phosphorus-O-methyl, I + systemic phosphorus-S, I + systemic phosphorus-S-methyl, I + systemic phosphorus-S-methyl sulfone, I + butyl ether urea, I + chlorimide, I + diaminophosphine, I + diazinon, I + isochloride, I + chlorpyrifos, I + dichlorvos, I +Dicliphos, I + dicresyl, I + phosmet, I + dichlorvos, I + diethyl-5-methylpyrazol-3-yl phosphate, I + diflubenzuron, I + dilor, I + tetrafluoromethrin, I + methamidophos, I + dimethoate, I + permethrin, I + methyl chlorpyrifos, I + difenoconazole, I + dinex-diclexine, I + propargite, I + pendimethalin, I + danochlor, I + fipronil, I + benzyl benzoate, I + dioxin, I + dioxin, I + dioxin, I + ethion, I + dithicrofos, I + DNOC, I + doxycycline, I + dioxin DSP, I + Ecdysone, I + EI 1642, I + Abamectin, I + Abamectin Benzoate, I + EMPC, I + Enzyme, I + Endothiophanate-methyl, I + Indomethacin, I + Dichlorvos, I + EPBP, I + EPN, I + Jujube, I + Erinocetyl, I + Cypermethrin, I + Etaphos, I + Ethiophanate-methyl, I + Ethiophanate-methyl, I + Ethiophanate-methyl, I + Ethyl Formate, I + Ethyl-DDD, I + Ethyl Dibromide, I + Ethyl Dichloride, I + Ethylene Oxide, I + Ethylpyridinium Chloride, I + Ethylene Oxide, I + Ethylpyridinium Chloride, I + EXD, I + Ammonium Chloride, I + Benzoate, I + Acaricide, I + Flyphosate, I + Benthiocarb, I + Fenfluridine, I + Fenitrothion, I + Butafencarb, I + Fenoxacrim, I + Fenoxycarb, I + Cypermethrin, I + Cypermethrin, I + Fenpyrad, I + Fonsophos, I + Fenthiocarb-ethyl, I + Cypermethrin, I + Fipronil, I + Flufenoxuron, I + Flufenoxuron, I + Flucofuron, I + Flucyclovir, I + Bifenazate, I + Pyrimethanil, I + Flufenoxuron, I + Trifluralin, I + Flufenoxuron, I + Flufenoxuron, I + FMC 1137, I + Terbufos, I + Amitraz, I + Amitraz hydrochloride, I+ fenpropathrin, I+ formparanate, I+ buprofen, I+ forsporanic acid, I+ thiazolidinone, I+ thiamethoxam, I+ furazolidone, I+Pyrethrum, I + γ-cyhalothrin, I + γ-HCH, I + biguanide salt, I + biguanide acetate, I + GY-81, I + benzylpyr, I + chlorfenapyr, I + HCH, I + HEOD, I + fenpropathrin, I + fenpropathrin, I + flufenoxuron, I + HHDN, I + flufenoxuron, I + hydrocyanic acid, I + acetamiprid, I + hyquincarb, I + imidacloprid, I + propargite, I + indoxacarb, I + iodomethane, I + IPSP, I + chlorpyrifos, I + carbamate, I + methamidophos, I + isofenphos, I + transplanting agent, I + isoprocarb, I + O-(methoxyaminothiophosphoryl)salicylic acid isopropyl ester, I + isoprothiolane, I + isoprothiolane, I + oxazolidin, I + ivermectin, I + jatrophain I, I + jatrophain II, I + iodophos, I + juvenile hormone I, I + juvenile hormone II, I + juvenile hormone III, I + chlorpyrifos, I + acetamiprid, I + lambda-cyhalothrin, I + lead arsenate, I + rapamycin, I + parabromophos, I + lindane, I + lirimfos, I + lufenuron, I + thiamethoxam, I + m-isopropylphenyl methyl carbamate, I + magnesium phosphide, I + malathion, I + terfenadine, I + azidophos, I + pymetrozine, I + tetramethrin, I + pymetrozine, I + Dimethoate, I + Mercurous chloride, I + Mesulfenfos, I + Cyfluthrin, I + Vermicompost, I + Vermicompost Potassium, I + Vermicompost Sodium, I + Acaricide, I + Methamidophos, I + Methanesulfonyl Fluoride, I + Chlorpyrifos, I + Methionol, I + Ethylmethoxyfenozide, I + Methomyl, I + Acetaminophen, I + Methionyl DDT, I + Methoxybenzoyl, I + Methyl bromide, I + Methyl isothiocyanate, I + Methyl chloroform, I + Dichloromethane, I + Methionyl methoxyfenozide, I + Mefenoxam, I + Mefenoxam, I + Zicobam, I + Mimethin, I + Mimethin, I + Profenofos, I + Mimethrin, I + Phosphorus, I + Phosphine, I + Moxifloxacin, I + Naphthylphosphide, I + Dibromophos, I + Naphthalene, I + NC-170, I + NC-184, I + Nicotine, I + Nicotine Sulfate, I + Flufenoxuron, I + Acetaminophen, I + Nithiazoxazole, I + Pendimethalin, I +Cypermethrin 1:1 zinc chloride complex, I + NNI-0101, I + NNI-0250, I + Nornicotinic acid, I + Bis(fluorourea), I + Polyfluorourea, I + O-5-dichloro-4-iodophenyl O-ethyl ethyl thiophosphonate, I + O,O-diethyl O-4-methyl-2-oxo-2H-chromene-7-yl thiophosphonate, I + O,O-diethyl O-6-methyl-2-propylpyrimidin-4-yl thiophosphonate, I + O,O,O',O'-tetrapropyl dithiophosphate, I + Oleic acid, I + Omethoate, I + Carbendazim, I + Sulfonylphosphonate-methyl, I + Isosulfonylphosphonate, I + Sulfonylphosphonate, I + pp'-DDT, I + p-dichlorobenzene, I + parathion, I + parathion-methyl, I + Fluorouracil, I + Pentachlorophenol, I + pentachlorophenyl laurate, I + permethrin, I + petroleum oils, I + pH 60-38, I + fenthion, I + fenpropathrin, I + phosphamidon, I + phorate + TX, I + phosmet, I + thiocyclam, I + phosphamidon, I + parathion, I + phosphamidon, I + phoxim, I + phoxim-methyl, I + pirimetaphos, I + pirimetaphos, I + chlorfenapyr-ethyl, I + chlorfenapyr-methyl, I + polyvinyl chloride dicyclopentadiene isomers, I + polyvinyl chloride terpenes, I + potassium arsenite, I + potassium thiocyanate, I + pyrethrin, I + precocial agent I, I + precocial agent II, I + precocial agent III, I + Primidophos, I + Profenofos, I + Fenflurphos, I + Carbendazim, I + Moxacarb, I + Profenofos, I + Amphetamine, I + Procymidone, I + Ethiazophos, I + Profenofos, I + Phoxim, I + Protrifenbute, I + Pymetrozine, I + Pyrazophos, I + Phoxim, I + Pyresmethrin, I + Pyrethrin I, I + Pyrethrin II, I + Pyrethroids, I + Pyridaben, I + Acetaminophen, I + Pyrazophos, I + Pyrazophos, I + Pyriproxyfen, I + Pyriproxyfen, I + Quassia, I + Quinalphos, I + Quinalphos-methyl, I + Phoxim, I + Quintiofos, I+R-1492, I+Rifonitrile, I+Benzothrin, I+Rotenone, I+RU 15525, I+RU 25475, I+Ryania, I + Rianodin, I + Veratrum nigrum, I + octophos, I + thion, I + selamectin, I + SI-0009, I + SI-0205, I + SI-0404, I + SI-0405, I + flumethrin, I + SN 72129, I + sodium arsenite, I + sodium cyanide, I + sodium fluoride, I + sodium hexafluorosilicate, I + sodium pentachlorophenate, I + sodium selenate, I + sodium thiocyanate, I + thiophanate-methyl, I + spinosad, I + spirodiclofen, I + spirotetramat, I + sulcofuron, I + sulcofuron-sodium, I + fipronil, I + fenitrothion, I + sulfonyl fluoride, I + Phosphate, I + Tar compounds, I + τ-flufenoxam, I + thiamethoxam, I + TDE, I + tebufenozide, I + pyridaben, I + butylpyrimidine, I + flufenoxuron, I + heptafluthrin, I + dithion, I + TEPP, I + cyclopentylpyrethrin, I + terbam, I + terbufos, I + tetrachloroethane, I + chlorpyrifos, I + tetramethrin, I + θ-cypermethrin, I + thiafenoxam, I + thiamethoxam, I + thiophanate-methyl, I + chlorpyrifos, I + chlorpyrifos, I + chlorpyrifos, I + chlorpyrifos, I + thiamethoxam ... Thiosultap, I + thiosultap-sodium, I + Bacillus thuringiensis, I + acetamiprid, I + tetrabromopyrethrin, I + tetrafluorobenzylpyrethrin, I + transpermethrin, I + cypermethrin, I + azoxystrobin, I + triazophos, I + trichlorfon, I + trichlorfon-3, I + phosphamidon, I + trichlorfon, I + chlorfenapyr, I + chlorfenapyr, I + chlorfenapyr, I + acetamiprid, I + acetamiprid, I + vaniliprole, I + veratrine, I + veratrine, I + XMC, I + methomyl, I + YI-5302, I + ζ-cypermethrin, I + zetamethrin, I + Zinc phosphide, I+ thiamethoxam (zolaprofos), and ZXI 8901, I+ cyantraniliprole, I+ chlorantraniliprole, I...+ Cyenopyrafen, I + Fipronil, I + Pyrifluquinazon, I + Spinetoram, I + Spirotetramethrin, I + Sulfoxaflor, I + Flufiprole, I + Cypermethrin, I + Tetramethylfluthrin, I + Triflumezopyrim.

[0146] Compositions containing molluscicides include: I + bis(tributyltin) oxide, I + bromoacetamide, I + calcium arsenate, I + cloethocarb, I + copper acetylacetate, I + copper sulfate, I + triphenyltin, I + ferric phosphate, I + metaldehyde, I + cypermethrin, I + niclosamide, I + niclosamide ethanolamine salt, I + pentachlorophenol, I + sodium pentachlorophenoxide, I + tazimcarb, I + thiamethoxam, I + tributyltin oxide, I + trifenmorph, I + trimethacarb, I + triphenyltin acetate and triphenyltin hydroxide, I + pyriprole.

[0147] Compositions containing nematicides include: I + AKD-3088, I + 1,2-dibromo-3-chloropropane, I + 1,2-dichloropropane, I + 1,2-dichloropropane and 1,3-dichloropropene, I + 1,3-dichloropropene, I + 3,4-dichlorotetrahydrothiophene 1,1-dioxide, I + 3-(4-chlorophenyl)-5-methylrhodanine, I + 5-methyl-6-thio-1,3,5-Thiadiazidin-3-ylacetic acid, I + 6-isopentenylaminopurine, I + abamectin, I + acetamiprid, I + malathion, I + thiamethoxam, I + AZ 60541, I + benzylchlorothiazide, I + benzoylpyridaben, I + cadusafos, I + carbofuran, I + carbon disulfide, I + thiocarbofuran, I + chloropicrin, I + chlorpyrifos, I + cloethocarb, I + cytokinins, I + dazomet, I + DBCP, I + DCIP, I + diamidophos, I + dichlofenthion, I + didicophosphate, I + dimethoate, I + Dolactin, I + Imacidine, I + Imacidine Benzoate, I + Irinokine, I + Fenamiphos, I + Dibromoethane, I + Fenamiphos, I + Fenpyrad, I + Fonshiazate, I + Fosthietan, I + Furfural, I + GY-81, I + Heterophos, I + Iodim, I + Imidofos, I + Iazofos, I + Ivermectin, I + Mecarphon, I + Fenamiphos Potassium Salt, I + Fenamiphos Sodium Salt, I + Methyl Bromide, I + Methyl Isothiocyanate, I + Milbemycin Oxime, I + Moxifloxacin, I + Myrothecium verrucaria component, I + NC-184, I + chlorpyrifos, I + phorate, I + phosphocarb, I + sebufos, I + selamectin, I + spinosad, I + terbam, I + terbufos, I + tetrachlorothiophene, I + thifenzin, I + triazophos, I + triazophos, I + xylenephenol, I + YI-5302 and zeatin, I + fluensulfone.

[0148] Compositions containing synergists include: I + 2-(2-butoxyethoxy)ethyl piperonyl ester, I + 5-(1,3-benzodioxane-5-yl)-3-hexylcyclohex-2-enone, I + farnesol with nerolidol, I + MB-599, I + MGK 264, I + piperonyl butoxide, I + piperonal, I + propyl isomer, I + S421, I + sesamex, I + sesasmolin, and I + sulfoxide.

[0149] Compositions containing animal repellents include: I+anthraquinone, I+chloralose, I+copper naphthenate, I+copper oxychloride, I+diazinon, I+dicyclopentadiene, I+guazatine, I+biguanidine acetate, I+carbamate, I+pyridine-4-amine, I+serum, I+trimethacarb, I+zinc naphthenate, and I+zinc thiram.

[0150] Other compositions include: I + Brofluthrinate, I + Cycloxaprid, I + Diflovidazine, I + Flometoquin, I + Fluhexafon, I + Guadipyr, I + Plutella xylostella Granulosis virus, I + Cydia pomonella Granulosis virus, I + Harpin, I + Imicyafos, I + Heliothis virescens Nucleopolyhedrovirus, I + Heliothis punctigera Nucleopolyhedrovirus, I + Helicoverpaarmigera Nucleopolyhedrovirus, I + Helicoverpa zea Nucleopolyhedrovirus, I+ Spodoptera frugiperda Nucleopolyhedrovirus, I+ Plutella xylostella Nucleopolyhedrovirus, I+ Pasteuria nishizawae, I+ p-cymene, I+ Pyflubumide, I+ Pyrafluprole, I+ pyrethrum, I+ QRD 420, I+ QRD 452, I+ QRD 460, I+ Terpenoid blends, I+ Terpenoids, I+ Tetraniliprole, and I+ α-terpinene.

[0151] The composition further includes a mixture of one or more polymorphs of the present invention with active substances referenced by the following codes, such as I+code AE ​​1887196 (BSC-BX60309), I+code NNI-0745 GR, I+code IKI-3106, I+code JT-L001, I+code ZNQ-08056, I+code IPPA152201, I+code HNPC-A9908 (CAS: [660411-21-2]), I+code HNPC-A2005 (CAS: [860028-12-2]), I+code JS118, I+code ZJ0967, I+code ZJ2242, I+code JS7119 (CAS: [929545-74-4]), I+code SN-1172, I... +Code HNPC-A9835, I +Code HNPC-A9955, I +Code HNPC-A3061, I +Code Chuanhua 89-1, I +Code IPP-10, I +Code ZJ3265, I +Code JS9117, I +Code SYP-9080, I +Code ZJ3757, I +Code ZJ4042, I +Code ZJ4014, I +Code ITM-121, I +Code DPX-RAB55 (DKI-2301), I +Code Me5382, I +Code NC-515, I +Code NA-89, I +Code MIE-1209, I +Code MCI-8007, I +Code BCS-CL73507, I +Code S-1871, I + The code is DPX-RDS63, and the I+ code is AKD-1193.

[0152] Although compositions comprising one or more polymorphs of the present invention and another insecticide, etc., have been clearly disclosed above, those skilled in the art will understand that the invention extends to ternary compounds, as well as various other combinations comprising the aforementioned binary mixtures.

[0153] The weight ratio of one or more polymorphs of the present invention to another insecticide is generally between 1000:1 and 1:100, more preferably between 500:1 and 1:100, for example between 250:1 and 1:66, between 125:1 and 1:33, between 100:1 and 1:25, between 66:1 and 1:10, between 33:1 and 1:5, and between 8:1 and 1:3.

[0154] The polymorphs of this invention are also used in the field of animal health, for example, they can be used to combat parasitic invertebrate pests, more preferably, to combat parasitic invertebrate pests inside or on the surface of animals. Examples of pests include nematodes, flukes, tapeworms, flies, mites, ticks, lice, fleas, stink bugs, and maggots. The animals may be non-human animals, such as agricultural animals like cattle, pigs, sheep, goats, horses, or donkeys, or pet animals like dogs or cats.

[0155] In another aspect, the present invention provides a polymorph of the invention for use in medical treatment methods.

[0156] In another aspect, the present invention relates to a method for controlling parasitic invertebrate pests within or on the surface of an animal, the method comprising administering an effective amount of the polymorph of the present invention for killing the pest. The administration may be, for example, oral, non-gastrointestinal, or external, such as to the surface of the animal's body. In another aspect, the present invention relates to the use of the polymorph of the present invention for controlling parasitic invertebrate pests within or on the surface of an animal. In yet another aspect, the present invention relates to the use of the polymorph of the present invention in the preparation of pharmaceutical agents for controlling parasitic invertebrate pests within or on the surface of an animal.

[0157] In another aspect, the present invention relates to a method for controlling parasitic invertebrate pests, the method comprising administering a pest-killing amount of the polymorph of the present invention to the environment in which the animal inhabits.

[0158] In another aspect, the present invention relates to a method for protecting animals from parasitic invertebrate pests, the method comprising administering the animal an effective amount of the polymorph of the present invention to kill the pests. In another aspect, the present invention relates to the use of the polymorph of the present invention for protecting animals from parasitic invertebrate pests. In yet another aspect, the present invention relates to the use of the polymorph of the present invention in the preparation of pharmaceutical agents for protecting animals from parasitic invertebrate pests.

[0159] In another aspect, the present invention provides a method for treating animals infested by parasitic invertebrate pests, the method comprising administering to the animal an effective amount of the polymorph of the present invention for killing the pest. In another aspect, the present invention relates to the use of the polymorph of the present invention for treating animals infested by parasitic invertebrate pests. In yet another aspect, the present invention relates to the use of the polymorph of the present invention in the preparation of a medicament for treating animals infested by parasitic invertebrate pests.

[0160] In another aspect, the present invention provides a pharmaceutical composition comprising the polymorph of the present invention and a pharmaceutically suitable excipient.

[0161] The polymorphs of the present invention can be used alone or in combination with one or more other bioactive ingredients.

[0162] In one aspect, the present invention provides a composite product comprising a biocidally effective amount of component A and a biocidally effective amount of component B, wherein component A is a polymorph of the present invention and compound B is a compound described below.

[0163] The polymorphs of the present invention can be used in combination with anthelmintic agents. Such anthelmintic agents include compounds selected from macrolides, such as ivermectin, abamectin, imamectin, irinotecan, dolactin, silacritin, moxicritin, nemectin, and milbemycin derivatives, as described in EP-357460, EP-444964, and EP-594291. Other anthelmintic agents include semi-synthetic and biosynthetic ivermectin / milbemycin derivatives, such as those described in US-5015630, WO-9415944, and WO-9522552. Further anthelmintic agents include benzimidazoles, such as albendazole, canbendazole, fenbendazole, flubendazole, mebendazole, oxifendazole, ocendazole, perbendazole, and other members of the aforementioned class. Other anthelmintics include imidazothiazoles and tetrahydropyrimidines, such as tetraimidazole, levamisole, pyrantel pamoate, octetil, or molentaxel. Other anthelmintics include trematodes (such as triclofenac and clostridium) and tapeworms (such as praziquantel and estataxel).

[0164] The polymorphs of the present invention can be used in combination with derivatives and analogs of paraherquamide / marcfortine anthelmintics and antiparasitic oxazolines (such as those disclosed in US-5478855, US-4639771 and DE-19520936).

[0165] The polymorphs of the present invention can be used in combination with derivatives and analogs of general types of dioxomorphic antiparasitic agents as described in WO-9615121, as well as with cyclic phenyl condensates with anthelmintic activity (such as those described in WO-9611945, WO-9319053, WO-9325543, EP-626375, EP-382173, WO-9419334, EP-382173, and EP-503538).

[0166] The polymorph of the present invention can be used in combination with other ectoparasite-killing agents; for example, fipronil; pyrethroids; organophosphates; insect growth regulators such as clofenuron; molting hormone agonists such as tebufenozide; neonicotinoids such as imidacloprid.

[0167] The polymorphs of the present invention can be used in combination with terpene alkaloids, such as those described in International Patent Application Publication Nos. WO95 / 19363 or WO 04 / 72086, and in particular the compounds disclosed therein.

[0168] Other examples of such bioactive compounds that can be used in combination with the polymorphs of the present invention include, but are not limited to, the following: Organophosphates: Acetaminophen, Methylpyrazine, Ethyl glutathione, Methyl glutathione, Bromothione, Ethyl Bromothione, Thiophanate, Chlorethoxyphos, Chlorpyrifos, Chlorfenapyr, Demeton-methyl, Demeton-S-methyl sulfone, Chlorimide, Diazinon, Dichlorvos, Phosphate, Dimethoate, Ethiophanate-methyl, Ethiophanate-methyl, Ethiophanate-methyl, Oxypyridazine, Valdex, Benzophos, Fenitrothion, Fonsophos, Fenthion, Pyralidoxime, Terbufos, Ango, Thiazolium Phosphate, Heptenphos, Chlorpyrifos, Isoprophos, Isoxazolium Phosphate, Ma... Phosphine, chlorfenapyr, methamidophos, chlorpyrifos, methyl parathion, methamidophos, phosmet, dibromophos, omethoate, methyl oxyphosphazene, paraoxon, parathion, methyl parathion, pyridaben, thiophanate-methyl, phosmet, phosmet, phosmet, phosmet, phorate, phosmet-methyl, phosmet, phosmet, proetamphos, pyridaben, pyridaben, quinalazine, thiophanate-methyl, thiophanate-methyl, phosmet, phosmet, pyridaben, pyridaben, pyridaben, phosmet, thiophanate-methyl, phosmet, phosmet, terbufos, butylpyrimidine, phosmet, thimeton, triazophos, trichlorfon, phosmet.

[0169] Carbamates: Carbofuran, Aldicarb, 2-sec-butylphenylmethylcarbamate, Propylene carbofuran, Sevin, Carbofuran, Butylcarbofuran, Carbofuran, Ethylbenzylcarbide, Phenoxycarbide, Fenthiazine, Furazolidone, HCN-801, Isopropylcarbide, Indomethacin, Methomyl, 5-Methyl-m-isopropylphenylbutynyl (methyl)carbamate, Apimethoate, Pyriproxyfen, Prochloraz, Thiamethoxam, Dimethoate, Apimethoate, UC-51717.

[0170] Pyrethroids: Flufenoxuron, Allylpyrrolidone, Cis-Cypermethrin, 5-Benzyl-3-furanmethyl(E)-(1R)-cis-2,2-dimethyl-3-(2-oxothiacyclopentane-3-ylidenemethyl)cyclopropanecarboxylate, Bifenthrin, β-Cypermethrin, Flufenoxuron, α-Cypermethrin, β-Cypermethrin, Bioallethrin, Bioallethrin ((S)-cyclopentyl isomer), Biobenzylfuran, Bifenthrin, NCI-85193, Cypermethrin, Trifluralin Esters, cypermethrin, deltamethrin, fenpyrocyanide, fenpyrocyanide, pyrethroid, fenpyrocyanide, pendimethalin, cypermethrin, fenpyrocyanide, flufenmethrin, flufenmethrin, cypermethrin (D isomer), fenpyrocyanide, trifluorocypermethrin, λ-high-efficiency cypermethrin, benzylpyrethrin, fenpyrocyanide, pyrethroid, pyrethroid (natural product), benzylfuran, fenpyrocyanide, tetrafluorocypermethrin, θ-cypermethrin, flusilylpyrethrin, t-flumethrin, heptafluorocyanide, tetrabromopyrethrin, ζ-cypermethrin.

[0171] Arthropod growth regulators: a) Chitosan synthesis inhibitors: Benzoylurea: diflubenzuron, fenflurfen, acetamiprid, flufenoxuron, flufenoxuron, flufenuron, chlorfenuron, difenflurfen, fenflurfen, chlorfenapyr, thiamethoxam, benzyl ether, thiamethoxam, etoxazole, chlorfenapyr; b) Ecdysone antagonists: chlorfenapyr, methoxyfenozide, tebufenozide; c) Juvenile hormone analogs: fenflurfen, methoxyprine (including S-methoxyprine), phenoxycarb; d) Lipid biosynthesis inhibitors: spirodiclofen.

[0172] Other antiparasitic drugs: Acaricide, Amitraz, AKD-1022, ANS-118, Azadirachtin, Bacillus thuringiensis, Cypermethrin, Bifenazate, Acaricide, Bromopropylate, BTG-504, BTG-505, Toxaphene, Mefenoxam, Difenoconazole, Acaricide, Bromnifloxacin, Cyclodinafop-methyl, Thiamethoxam, Dimethomorph, Dicloden, Acaricide, DBI-3204, Dichlorophenoxyacetic acid, Dihydroxybenzene Methyl dihydroxypyrrolidine, fenpyroximate, fenpyroximate, endosulfan, acetamiprid, permethrin, quinclorac, flumite, MTI-800, azoxystrobin, pyrimethanil, flufenoxuron, deltamethrin, flufenoxuron, trifluralin, fluproxyfen, halofenprox, flufenoxuron, IKI-220, sodium silicate, NC-196, Indian mint (neem) guard), nidinorterfuran, acetamiprid, SD-35651, WL-108477, acetamiprid, clopyralid, protrifenbute, pymetrozine, pyridaben, pyrimethanil, NC-1111, R-195, RH-0345, RH-2485, RYI-210, S-1283, S-1833, SI-8601, flusilyl ester, silomadine, spinosad, pymetrozine, trichlorfon, tetracycline, thiamethoxam, chlorpyrifos, thiamethoxam, azoxystrobin, pymetrozine, spinosad, trichlorfon, synergistic acetylacetonate, vertalec, YI-5301.

[0173] Fungicides: Activated ester, 4-dodecyl-2,6-dimethylmorpholine, 1-aminopropyl phosphate, amine methamidophos, azaconazole, azoxystrobin, benomyl, cymoxanil, pyraclostrobin, blast fungicide-S, Bordeaux mixture, furazolidone, ethirimol sulfonate, cyproconazole, captan, carbendazim, chlorfenazole, dimethoate, chloropicrin, chlorothalonil, ethoxysulfuron, basic copper chloride, copper salts, cyclophosphamide, cymoxanil Cycloconazole, azoxystrobin, pyraclostrobin, RH-7281, diclofenac, benzyltriazole, pyridaben, chlorpyrifos, difenoconazole, RP-407213, dimethomorph, fenpyroximide, tebuconazole, tebuconazole-M, styracil, oxypyrrolizumab, oxadiazon, imidacloprid, chlorpyrifos, fencaramid, seed dressing agent, benzyl benzoate, butyl morpholine, triphenyltin acetate, fluazinam, fludioxonil, flumethrin Flumorf / flumorlin, styrax, fluazinam, fluquinazole, flusilazole, fluamide, fenbendazole, captan, fosetyl-aluminum, furazolidone, flavobacterium, hexaconazole, tebuconazole, isoprothiolane, isoprothiolane, isoprothiolane, kasugamycin, azoxystrobin, mancozeb, mancozeb, metalaxyl, cymoxanil, tebuconazole, metominostrobin / fenominostrob (in), benomyl, cyproconazole, ferric ammonium, cyazofamid, oxadiazon, cyclophosphamide, tebuconazole, pendimethalin, thiamethoxam, propiconazole, cymoxanil, propiconazole, propoxyquin, prothioconazole, pyraclostrobin, pyrimethanil, quinclorac, spirocycline, sulfur, tebuconazole, flufenoxuron, thiabendazole, thifluzamide, thiophanate-methyl, silane, thiabendazole, triadimefon, triadimefon, tricyclazole, oxadiazon, styraxazole, fenbendazole, jinggangmycin, vinclozolin.

[0174] Biological agents: Bacillus thuringiensis ssp aizawai, Bacillus thuringiensis kurstaki, Bacillus thuringiensis δ endotoxin, baculoviruses, entomopathogenic bacteria, viruses, and fungi.

[0175] Bactericides: chlortetracycline, oxytetracycline, streptomycin.

[0176] Other biological agents: Enflufloxacin, Febantal, Pensacillin, Meloxicam, Cephalexin, Kanamycin, Pimoben, Clenbuterol, Omeprazole, Thiemlin, Benazepril, Pyriprole, Cefquinoxime, Florfenicol, Buserelin, Cefavirenz, Tolazoline, Ceftiofur, Carbofenac, Cyfluthrin, Praziquantel, Triclofenadazole.

[0177] When used in combination with other active ingredients, the polymorphs of the present invention are preferably used in combination with the following: imidacloprid, enflufloxacin, praziquantel, pyrantel embonate, febantal, pentazocine, meloxicam, cephalexin, kanamycin, pimoxim, clenbuterol, fipronil, ivermectin, omeprazole, thiamethoxam, benazepril, mibexyphenidyl, cypermethrin, thiamethoxam, pyriprole, deltamethrin, cefoquinoxime, florfenicol, buceroxim, cefovecin, toraconazole, ceftiofur, silaclofen, carbofen, cyfluthrin, moxifloxacin, tebufenozide (including S-tebufenozide), chlorpyrifos. Sulon, pyrantel pamoate, amitraz, trichlorobenzazole, avermectin, abametin, imazalil, irinotecan, dolactin, silacritin, nemesistin, albendazole, canbendazole, fenbendazole, flubendazole, mebendazole, oxifendazole, oxifendazole, pabendazole, tetramisole, levamisole, pyrantel pamoate, octetil, molentaxel, trichlorobenzazole, esetil, fipronil, lufenuron, ecdysone, or tebufenozide; more preferably, in combination with the following: enflufloxacin, praziquantel, pyrantel pamoate. Fibentel, Pensacillin, Meloxicam, Cephalexin, Kanamycin, Pimoben, Clenbuterol, Omeprazole, Thiemlin, Benazepril, Piriprednisolone, Cefquinoxime, Florfenicol, Buterlein, Cefotaxime, Tolazoline, Ceftiofur, Slacutane, Carbofen, Moxifloxacin, Closulon, Tiapril, Irinoctin, Dolactin, Slacutane, Nemectin, Albendazole, Canbendazole, Fenbendazole, Flubendazole, Mebendazole, Oxendazole, Oxendazole, Pabendazole, Tetraimidazole, Levamisole Pamoate, octetil, molentel, triclobenzazole, esetel, lufenuron, or ecdysone; or more preferably in combination with the following: enflufloxacin, praziquantel, pamoate, febantel, pentazocine, meloxicam, cephalexin, kanamycin, pimoben, clenbuterol, omeprazole, thimazole, benazepril, piracetam, cefquinoxime, florfenicol, buserelin, cefotaxime, tolazoline, ceftiofur, slaketine, carbofenoxuron, moxifloxacin, closulon, or pamoate.

[0178] One combination is particularly noteworthy, wherein the additional active ingredient has a different site of action than the polymorph of the present invention. In some cases, combination with at least one other parasitic invertebrate control active ingredient having a similar control spectrum but a different site of action will be particularly advantageous for resistance management. Therefore, the combined products of the present invention may include a pest-killing effective amount of the polymorph of the present invention and a pest-killing effective amount of at least one other parasitic invertebrate control active ingredient having a similar control spectrum but a different site of action.

[0179] Those skilled in the art will recognize that salts also possess biological benefits in their non-salt forms because the salts of compounds are in equilibrium with their corresponding non-salt forms in the environment and under physiological conditions.

[0180] Therefore, the various salts of the polymorphs of the present invention (and the active ingredients used in combination with the active ingredients of the present invention) can be used to control invertebrate pests and animal parasites. The salts include acid addition salts formed with inorganic or organic acids such as hydrobromic acid, hydrochloric acid, nitric acid, phosphoric acid, sulfuric acid, acetic acid, butyric acid, fumaric acid, lactic acid, maleic acid, malonic acid, oxalic acid, propionic acid, salicylic acid, tartaric acid, 4-toluenesulfonic acid, or valeric acid. The polymorphs of the present invention also include N-oxides. Therefore, the present invention comprises combinations of the polymorphs of the present invention (including their N-oxides and salts) with additional active ingredients (including their N-oxides and salts).

[0181] Compositions intended for animal health may also contain formulation auxiliaries and additives known to those skilled in the art as formulation aids (some of which may also be considered as solid diluents, liquid diluents, or surfactants). Such formulation auxiliaries and additives can control: pH (buffers), foaming during processing (defoamers such as polysiloxanes), sedimentation of the active ingredient (suspending agents), viscosity (thixotropic thickeners), microbial growth within the container (antimicrobial agents), product freezing (antifreeze agents), color (dye / pigment dispersions), elution properties (film-forming agents or adhesives), evaporation (evaporation delay agents), and other formulation properties. Film-forming agents include, for example, polyvinyl acetate, polyvinyl acetate copolymers, polyvinylpyrrolidone-vinyl acetate copolymers, polyvinyl alcohol, polyvinyl alcohol copolymers, and waxes. Examples of formulation additives and auxiliaries include McCutcheon's Volume 2: Functional Materials, annual International and North American editions, published by McCutcheon's Division, The Manufacturing Confectioner Publishing Co.; and those listed in PCT Publication WO 03 / 024222.

[0182] The polymorphs of the present invention can be applied without other adjuvants, but most commonly, they are applied as formulations containing one or more active ingredients along with suitable carriers, diluents, and surfactants, and may be combined with food depending on the intended end use. One method of application involves spraying an aqueous dispersion or refined oil solution of these formulations. Compositions containing spray oil, spray oil concentrate, spreader sticker, adjuvant, other solvents, and synergists (such as piperonyl butyl ether) often enhance the efficacy of the compound. Such sprays can be applied from a spray container (such as a can, bottle, or other container) by means of a pump or by release from a pressurized container (such as a pressurized aerosol spray can). Such spray compositions can take many forms, such as sprays, mists, foams, smoke, or fog. Such spray compositions may therefore further include propellants, foaming agents, etc., depending on the specific circumstances. Notably, one spray composition contains a biocideally effective amount of the compound of the present invention and a carrier. One embodiment of this spray composition includes a biocideally effective amount of the compound of the present invention and a propellant. Representative propellants include (but are not limited to) methane, ethane, propane, butane, isobutane, butene, pentane, isopentane, neopentane, pentene, hydrofluorocarbons, chlorofluorocarbons, dimethyl ether, and mixtures thereof. Of particular interest is a spray composition (and a method of using such a spray composition dispensed from a spray container) for controlling at least one parasitic invertebrate pest selected from the group consisting of mosquitoes, black flies, stable flies, deer flies, horseflies, wasps, bumblebees, ticks, spiders, ants, black flies, and the like, including alone or in combination.

[0183] Controlling animal parasites includes controlling ectoparasites that live on the surface of the host animal (e.g., shoulders, armpits, abdomen, inner thighs) and endoparasites that live inside the host animal (e.g., stomach, intestines, lungs, veins, subcutaneous tissue, lymphatic tissue). Ectoparasites or disease-carrying pests include, for example, chiggers, ticks, lice, mosquitoes, flies, mites, and fleas. Endoparasites include canine heartworms, hookworms, and worms. The polymorphs of this invention are particularly suitable for combating ectoparasitic pests. The polymorphs of this invention are also suitable for controlling parasite infestation or infection in animals, both systemically and / or non-systemically.

[0184] The polymorphs of this invention are applicable to combating parasitic invertebrate pests in infecting animal subjects, including wild animals, livestock, and agricultural working animals. Livestock is a term used to refer (singular or plural) to domesticated animals intentionally raised in an agricultural environment for the production of food or fiber, or their labor; examples of livestock include cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, hens, turkeys, ducks, and geese (e.g., raised for meat, milk, butter, eggs, fur, leather, feathers, and / or wool). By combating parasites, mortality and efficiency (in terms of meat, milk, wool, fur, eggs, etc.) are reduced, thus allowing for more economical and simpler animal husbandry practices through the application of the polymorphs of this invention.

[0185] The polymorphs of the present invention are applicable to combating parasitic invertebrate pests that infect companion animals and pets (e.g., dogs, cats, pet birds and ornamental fish), research and laboratory animals (e.g., hamsters, guinea pigs, rats and mice) in zoos, wild habitats and / or circuses.

[0186] In embodiments of the invention, the animal is preferably a vertebrate, and more preferably a mammal, bird, or fish. In one particular embodiment, the animal subject is a mammal (including great apes, such as humans). Other mammal subjects include primates (e.g., monkeys), bovids (e.g., cows or dairy cows), suidae (e.g., domestic pigs or pigs), sheep (e.g., goats or sheep), equines (e.g., horses), canids (e.g., dogs), felines (e.g., domestic cats), camels, deer, donkeys, buffalo, antelopes, rabbits, and rodents (e.g., guinea pigs, squirrels, rats, mice, gerbils, and hamsters). Birds include anatidae (swans, ducks, and geese), columbidae (e.g., doves and pigeons), pheasants (e.g., partridges, grouse, and turkeys), thesienidae (e.g., domestic chickens), psittacines (e.g., long-tailed parrots, macaws, and parrots), birds of prey, and ostriches.

[0187] Birds treated or protected by the polymorphs of this invention may be associated with commercial or non-commercial bird husbandry. These birds include, in particular, ducks raised for the pet or collectible market, such as swans, geese, and ducks; pigeons, such as doves and pigeons; pheasants, such as partridges, grouse, and turkeys; birds of prey, such as domestic chickens; and parrots, such as long-tailed parrots, macaws, and parrots.

[0188] For the purposes of this invention, the term "fish" is understood to include (but is not limited to) teleosts, i.e., bony fish. The orders Salmoniformes (including Salmonidae) and Perciformes (including Acanthodiana) are both included in teleosts. Examples of potential fish recipients include, in particular, Salmonidae, Serranidae, Seabreamidae, Cichlididae, and Acanthodiana.

[0189] Other animals are expected to benefit from the method of the present invention, including marsupials (such as kangaroos), reptiles (such as farmed turtles), and other livestock of significant economic value, for which the method of the present invention safely and effectively treats or prevents parasitic infections or infestations.

[0190] Examples of parasitic invertebrate pests controlled by administering an effective amount of the polymorph of the present invention to the protected animal include ectoparasites (arthropods, mites, etc.) and endoparasites (worms, such as nematodes, flukes, tapeworms, acanthocephalans, etc.).

[0191] Helminthiasis is a disease or group of diseases typically described as an infection of an animal host by parasites called worms. The term 'helminth' is intended to include nematodes, flukes, tapeworms, and acanthocephalans. Helminthiasis is a common and serious economic problem concerning domestic animals such as pigs, sheep, horses, cattle, goats, dogs, cats, and poultry.

[0192] The worm class described as nematodes causes widespread and sometimes serious infections in a variety of animal species.

[0193] Nematodes that can be treated with the polymorphs of the present invention include, but are not limited to, the following genera: *Echinops*, *Strongyloides felis*, *Ahrodontia*, *Strongyloides angiostrongylus*, *Ascaris*, *Ascaris*, *Brugia*, *Odontostomum*, *Capillaria*, *Chaetomium*, *C. cubitus*, *C. angiostrongylus*, *C. reticulata*, *C. bulgingii*, *C. spinosa*, *C. spp.*, *C. spp.*, *C. spp.*, *C. spp.*, *C. spp.*, *C. spp.*, *C. spp.*, *C. pinworm*, *C. spp. ... The genera *Ascaris lumbricoides*, *Loa*, *Mansonia*, *Müller*, *Cyclophora*, *Ceratophyllum*, *Ceratophyllum*, *Nodularia*, *Gastrocera*, *Ceratophyllum*, *Parasiticus*, *Parasiticus*, *Pterygophyllum*, *Protostrophus*, *Brachiaria*, *Ceratophyllum*, *Euphorbia*, *Strongyloides*, *Strongyloides*, *Strongyloides*, *Sucking Nematodes*, *Toxocara*, *Toxocara*, *Trichophyton*, *Trichophyton*, *Trichophyton*, *Trigon*, *Hookworm*, and *Wuce*.

[0194] Of the nematodes infecting these animals, the most common genera are *Haemaphysalis*, *Trichodina*, *Gastroceras*, *Nematoda*, *Cuppella*, *Ascaris*, *Odontostomum*, *Nodularia*, *Chaetomium*, *Strongyloides*, *Trichuris*, *Trichodina*, *Trichodina*, *Trichodina*, *Trichodina*, *Trichodina*, *Trichodina*, *Dictamnus*, *Capillaria*, *Heterostigma*, *Toxocara*, *Avian Ascaris*, *Caulis Acuminata*, *Hooktostomum*, *Hookworm*, *Toxocara*, and *Parascaris*. Some of these nematodes (such as *Trichodina*, *Cuppella*, and *Nodularia*) primarily invade the intestines, while others (such as *Haemaphysalis* and *Gastroceras*) are more prevalent in the stomach, and still others (such as *Dictamnus*) are found in the lungs. Other parasites can also reside in other tissues, such as the heart and blood vessels, subcutaneous and lymphatic tissues, and similar tissues.

[0195] The trematodes intended to be treated by the present invention and the method of the present invention include (but are not limited to) the following genera: Alaria, Fasciola, Dwarf Trematodes, Clonorchis, Paragonimus, and Schistosoma.

[0196] The tapeworms intended to be treated by the present invention and the method of the present invention include (but are not limited to) the following genera: *Sparganum*, *Diploporum*, *Spirometra*, and *Taenia*.

[0197] The most common genera of parasites in the human gastrointestinal tract are *Ahrodonta*, *Isodonta*, *Ascaris*, *Strongyloides*, *Trichodina*, *Capillaria*, *Trichuris*, and *Pinus*. Other medically important genera of parasites found in blood or tissues and organs outside the gastrointestinal tract include filarial worms such as *Wuceta*, *Brugia*, *Oncocephala*, and *Loa*, along with the extraintestinal stages of *Draconis* and intestinal worms such as *Strongyloides* and *Trichinella*.

[0198] Many other genera and species of worms are known in the art and are also considered for treatment by the polymorphs of the present invention. These are enumerated in great detail in: Textbook of Veterinary Clinical Parasitology, Volume 1, Helminths, EJL Soulsby, FA Davis Co., Philadelphia, PA. [Veterinary Clinical Parasitology Textbook, Volume 1, Helminths, EJL Soulsby, FA Davis Co., Philadelphia, PA]; Helminths, Arthropods and Protozoa, (6 th(6th Edition of Monnig's Veterinary Helminthology and Entomology), EJL Soulsby, Williams and Wilkins Co., Baltimore, Md. [Help, Arthropods and Protozoa, (6th Edition of Monnig's Veterinary Helminthology and Entomology), EJL Soulsby, Williams and Wilkins Co., Baltimore, MD]

[0199] The polymorphs of the present invention can effectively resist some animal ectoparasites (e.g., arthropod ectoparasites of mammals or birds).

[0200] Insect and mite pests include, for example, chewing insects (such as flies and mosquitoes), mites, ticks, lice, fleas, stink bugs, parasitic flies and similar organisms.

[0201] Adult flies include, for example, hornflies or bloodflies, horseflies or species of the genus *Tabernae*, stable flies or *Stomoxys calcitrans*, blackflies or *Gnaphalium*, deer flies or *Tabernae*, lice flies or sheep lice flies, and tsetse flies or *Tsetse flies* species. Parasitic fly larvae include, for example, *Drosophila* (sheep mad flies and yellow flies), blowflies or green flies, spiral maggots or cone maggots, striped dermatophytes or *Drosophila* species, woolly worms, and horse stomach flies. Mosquitoes include, for example, species of the genus *Culex*, *Anopheles*, and *Aedes*.

[0202] Mites include species from the order Mesosphala, such as species of the genus *Macrotrichum*, including chicken mites and chicken skin mites; scabies mites or itch mites, such as species of the family Sarcoptidae, including human scabies mite (Salpharcoptes scalphabiei); animal scabies mites, such as species of the genus *Ophiopogon*, including bovine itch mite and sheep itch mite; and chiggers, such as species of the genus *Chiggers*, including North American chiggers and *A. tsutchutii*.

[0203] Ticks include, for example, soft ticks, including species of the genus *Ixodes* such as species of the genus *Ixodes* and *Ixodes*; and hard ticks, including species of the genus *Ixodes* such as *Hemiberlesia serratifolia*, *Ixodes natans*, *Ixodes angustifolia*, *Ixodes natans*, *Ixodes scapulae*, and other species of the genus *Ixodes* (including the previously mentioned *Taurus japonicus*).

[0204] Lice include, for example, sucking lice, such as species of the genera *Avianus* and *Bovineus*; biting lice, such as species of the genera *Hymenopus*, *Gnaphalium*, and *Phyllostachys*.

[0205] Fleas include species of the genus *Ctenophora*, such as *Ctenophora canis* and *Ctenophora catis*; species of the genus *Ctenophora*, such as *Ctenophora orientalis*; and species of the genus *Flea*, such as *Flea irritans*.

[0206] Insects include, for example, the bed bug family or the common bed bug (temperate bed bug); species of the genus Tridentius, including Tridentius, also known as assassin bug; for example, the long red trident and other species of the genus Tridentius.

[0207] Flies, fleas, lice, mosquitoes, midges, mites, ticks, and worms typically cause significant damage to livestock and companion animals. Arthropod parasites are also a public nuisance and can serve as vectors for pathogens in both humans and animals.

[0208] Many other parasitic invertebrate pests are known in the art and are also considered for treatment by the polymorphs of the present invention. These are listed in great detail in: Medical and Veterinary Entomology, DS Kettle, John Wiley and Sons, New York and Toronto; Control of Arthropod Pests of Livestock: A Review of Technology, RO Drummand, JE George, and SE Kunz, CRC Press, Boca Raton, Florida.

[0209] The polymorphs of this invention can also effectively resist ectoparasites, including: flies such as *Gnaphalium affineum*, *Gnaphalium affineum* species, *Gnaphalium tsetseum* species, *Gnaphalium irritans* species, *Honeyfly*, *Honeyfly*, *Jack Fly*, *Horse Fly* species, *Botrytis cinerea*, *Betula spp.*, *Betula spp.*, *Betula spp.* species ..., *Betula spp.*, *Betula spp.*, *Betula spp.*, *Betula spp.*, *Betula spp.* species, *Betula spp.*, *Betula spp.*, *Betula spp.*, *Betula spp.* species, *Betula spp.*, *Betula spp.*, *Betula spp.* species, *Betula spp.*, *Betula spp.* species, *Betula spp.*, *Betula spp.* species, *Betula spp.*, *Betula spp.* species, *Betula Spiniger, spiny-toothed lice and dog-biting lice; sheep ticks such as sheep tick flies; and mites such as species of the genus *Ophiopogon*, human scabies mites, cattle scabies mites, horse tarantulas, species of the genus *Pyrhodochrum*, cat ear mites, species of the genus *Chilodon*, and ear scabies mites (ear mites).

[0210] The treatment of the present invention is administered in a conventional manner, such as by enteral administration in the form of tablets, capsules, beverages, infiltrated preparations, granules, pastes, pills, feed-through procedures, or suppositories; or by parenteral administration, such as by injection (including intramuscular, subcutaneous, intravenous, and intraperitoneal) or implantation; or by nasal administration.

[0211] When the polymorphs of the present invention are applied in combination with other bioactive ingredients, they can be administered individually, for example, as separate compositions. In this case, these bioactive ingredients can be administered simultaneously or sequentially. Alternatively, these bioactive ingredients can be components of a composition.

[0212] The polymorphs of the present invention can be administered in a controlled release form, such as a sustained-release formulation administered subcutaneously or orally.

[0213] Typically, the antiparasitic compositions according to the invention comprise the polymorph of the invention, optionally combined with another bioactive ingredient or its N-oxide or salt, and one or more pharmaceutically or veterinarily acceptable carriers comprising excipients and adjuvants selected according to standard specifications regarding the intended route of administration (e.g., oral or parenteral, such as injection). Furthermore, suitable carriers are selected based on compatibility with one or more active ingredients in the composition, including, for example, stability considerations relative to pH and moisture content. Therefore, it is noteworthy that the polymorphs of the invention protect animals from parasitic invertebrate pests, comprising an effective antiparasitic amount of the polymorph of the invention, optionally combined with another bioactive ingredient and at least one carrier.

[0214] For parenteral administration, including intravenous, intramuscular, and subcutaneous injections, the polymorphs of the present invention can be formulated in the form of suspensions, solutions, or emulsions in oily or aqueous media and may contain adjuvants such as suspending agents, stabilizers, and / or dispersants.

[0215] The polymorphs of the present invention can also be formulated for granulation injection or continuous infusion. Pharmaceutical compositions for injection comprise an aqueous solution of the active ingredient in a water-soluble form (e.g., a salt of the active compound), preferably in a physiologically compatible buffer containing other excipients or adjuvants known in the field of pharmaceutical formulations. Alternatively, suspensions of the active compound can be prepared in lipophilic media. Suitable lipophilic media include fatty oils (e.g., sesame oil), synthetic fatty acid esters (e.g., ethyl oleate and triglycerides), or materials (e.g., liposomes).

[0216] Aqueous injectable 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 forms (e.g., in ampoules or multi-dose containers). Alternatively, the active ingredient may be in powder form prior to use to combine with a suitable medium (e.g., sterile, pyrogen-free water).

[0217] In addition to the aforementioned formulations, the polymorphs of the present invention can also be formulated as long-acting preparations. Such long-acting preparations can be administered by implantation (e.g., subcutaneous or intramuscular) or by intramuscular or subcutaneous injection.

[0218] The polymorphs of the present invention can be formulated for this administration route with suitable polymers or hydrophobic materials (e.g., in the form of emulsions of pharmacologically acceptable oils), with ion exchange resins, or slightly soluble derivatives (such as (not limited to) sparingly soluble salts).

[0219] For inhalation administration, the polymorphs of the present invention can be delivered in the form of an aerosol spray using pressurized packaging or a nebulizer and a suitable propellant, such as (but not limited to) dichlorodifluoromethane, trichlorofluoromethane, dichlorotetrafluoroethane, or carbon dioxide. In the case of pressurized aerosols, the dosage unit can be controlled by providing a valve to deliver the metered amount.

[0220] Capsules and tubes made of gelatin, for example, for use in inhalers or blowpipes, can be formulated as a powder mixture containing the compound and a suitable powder base (such as lactose or starch).

[0221] The polymorphs of the present invention can possess favorable pharmacokinetic and pharmacodynamic properties, providing systemic availability through oral administration and ingestion. Therefore, upon ingestion by an animal to be protected, an effective concentration of the polymorphs of the present invention in the bloodstream, effective in killing parasites, can protect the treated animal from blood-sucking pests such as fleas, ticks, and lice. Thus, compositions that protect animals from parasitic invertebrate pests in oral administration (i.e., compositions comprising, in addition to an effective amount of the polymorphs of the present invention, one or more of a selection from binders and fillers suitable for oral administration and concentrated feed carriers) are noteworthy.

[0222] For oral administration in solutions (the most readily absorbed available form), emulsions, suspensions, pastes, gels, capsules, tablets, pellets, powders, granules, rumen-retention formulations, and feed / water / lick forms, the polymorphs of the present invention can be formulated with binders / fillers known in the art for oral administration, such as sugars and sugar derivatives (e.g., lactose, sucrose, mannitol, sorbitol), starches (e.g., corn starch, wheat starch, rice starch, potato starch), celluloses and derivatives (e.g., methylcellulose, carboxymethylcellulose, ethyl hydroxycellulose), protein derivatives (e.g., zein, gelatin), and synthetic polymers (e.g., polyvinyl alcohol, polyvinylpyrrolidone). Lubricants (e.g., magnesium stearate), disintegrants (e.g., croscarmellose, agar, alginate), and dyes or pigments may be added if desired. Pastes and gels often also contain adhesives (such as gum arabic, alginate, bentonite, cellulose, xanthan gum, colloidal magnesium aluminum silicate) to help keep the composition in contact with the mouth rather than easily spraying out.

[0223] In one embodiment, the compositions of the present invention are formulated into chewable and / or edible products (e.g., chewable therapeutic agents or edible tablets). The products will ideally have a taste, texture, and / or aroma preferred by the protected animal in order to facilitate oral administration of the compounds of the present invention.

[0224] If these antiparasitic compositions are in the form of a concentrated feed, the carrier is typically selected from high-performance feeds, feed grains, or protein concentrates. Such compositions containing concentrated feed may, in addition to the antiparasitic active ingredient, contain additives that promote animal health or growth and improve the meat quality of animals intended for slaughter or otherwise useful to livestock. These additives may include, for example, vitamins, antibiotics, chemotherapeutic agents, antibacterial agents, antifungal agents, coccidiostats, and hormones.

[0225] The polymorphs of the present invention can also be formulated into rectal compositions (such as suppositories or retention enemas) using, for example, conventional suppository bases (such as cocoa butter or other glycerides).

[0226] Formulations used in the methods of this invention may include antioxidants such as BHT (butyric acid). The antioxidants are generally present in amounts of 0.1% to 5% (wt / vol). Some formulations require a solubilizer (such as oleic acid) to dissolve the active agent, particularly if spinosad is included. Common spreading agents used in these pourable formulations include isopropyl myristate, isopropyl palmitate, and saturated C42-C ... 12 -C 18Fatty alcohols, including caprylic / capric esters, oleic acid, oleyl alcohol esters, ethyl oleate, triglycerides, silicone oils, and dipropylene glycol methyl ethers. The pouring formulations used in the method of the present invention are prepared according to known techniques. When the pour is a solution, the parasite / insecticide is mixed with a carrier or medium using heating and stirring (if necessary). Adjuvants or additional ingredients may be added to the mixture of the active agent and the carrier, or they may be mixed with the active agent prior to the addition of the carrier. Pouring formulations in emulsion or suspension form are similarly prepared using known techniques.

[0227] Other delivery systems can be used for relatively hydrophobic drug compounds. Liposomes and emulsions are well-known examples of delivery media or carriers for hydrophobic drugs. Additionally, organic solvents, such as dimethyl sulfoxide, can be used if desired.

[0228] The application rate (e.g., "bioeffective dose") required for effective control of parasitic invertebrate pests will depend on factors such as the species of the parasitic invertebrate pest to be controlled, the pest's life cycle, life stage, size, location, time of year, host crop or animal, feeding behavior, mating behavior, ambient humidity, temperature, and similar factors. Those skilled in the art can readily determine the bioeffective dose required to achieve the desired level of control over the parasitic invertebrate pest.

[0229] For general veterinary use, the polymorphs of the present invention provide pest-killing doses to animals, particularly warm-blooded animals, that require protection from parasitic invertebrate pests.

[0230] The effective dose for pest control is the amount of active ingredient required to achieve a noticeable reduction in the occurrence or viability of a target parasitic invertebrate pest. Those skilled in the art will understand that the effective dose for pest control can vary depending on the various compounds and compositions useful to the methods of the present invention, the desired pest-killing effect and duration, the target parasitic invertebrate pest species, the protected animal, the mode of application, and the like, and the amount required to achieve a specific result can be determined through simple experiments.

[0231] For animals administered orally or parenterally at appropriate time intervals, the dosage of the compositions of the invention is typically in the range of about 0.01 mg / kg to about 100 mg / kg, and preferably about 0.01 mg / kg to about 30 mg / kg of animal body weight.

[0232] The appropriate time interval for administering the compositions of the present invention to animals ranges from about once daily to about once a year. An administration interval ranging from about once weekly to about once every six months is noteworthy. A monthly administration interval (i.e., administering the compound to the animal once a month) is particularly noteworthy. Attached Figure Description

[0233] The invention will now be described with reference to the following non-limiting examples and accompanying drawings, wherein: Figure 1 The powder X-ray diffraction pattern of the polymorph named form A(a) is shown.

[0234] Figure 2 The predicted powder X-ray diffraction pattern of the polymorph named form A(a) is shown.

[0235] Figure 3 The DSC trace of the polymorph named form A(a) is shown.

[0236] Figure 4 The powder X-ray diffraction pattern of the polymorph named form A(b) is shown.

[0237] Figure 5 The DSC trace of the polymorph named form A(b) is shown.

[0238] Figure 6 The powder X-ray diffraction pattern of the hydrate of the compound having formula IA is shown.

[0239] Figure 7 The predicted powder X-ray diffraction pattern of the hydrate of the compound having formula IA is shown.

[0240] Figure 8 Powder X-ray diffraction patterns of polymorphs of compounds having formula IB are shown.

[0241] Figure 9 The DSC traces of polymorphs of compounds having formula IB are shown.

[0242] Figure 10 The predicted powder X-ray diffraction pattern of the polymorph of the compound having formula IB is shown.

[0243] Figure 11 Powder X-ray diffraction patterns of polymorphs of racemic compounds having formulas IA and ID are shown.

[0244] Figure 12 The DSC traces of polymorphs of racemic compounds having formulas IA and ID are shown.

[0245] Figure 13 The Raman spectrum of the polymorph named form A(a) is shown.

[0246] Figure 14 The DSC trace of the polymorph named form A(c) is shown. Detailed Implementation

[0247] Example

[0248] 1. Preparation of polymorphs

[0249] Compounds having formula I were prepared by the method described in WO 2011 / 067272. The resulting solid precipitate and liquid filtrate were analyzed by HPLC as shown in WO 2011 / 067272. Compounds having formula IA were present in the filtrate, and compounds having formula IC were present in the solid precipitate. When crystallized from the filtrate, the polymorph of form A(c) was identified by DSC (see [link to DSC]). Figure 14 ).

[0250] 1a. Preparation of form A(a)

[0251] The purified compound sample of formula IA was slurried in dimethyl carbonate at 25°C for 2 weeks, then the crystals were separated and characterized by DSC, powder X-ray diffraction, and single-crystal X-ray diffraction. The measured powder X-ray diffraction patterns of the polymorph of the compound of formula IA (designated as form A(a)) are shown in [the diagram]. Figure 1 The graph shown is a prediction from single-crystal intensity data. Figure 2 The DSC trace of form A(a) is shown in [the diagram]. Figure 3 As shown in the image.

[0252] 1b. Preparation of form A(b)

[0253] Another sample of the compound having formula IA was subjected to slow evaporation from various solvents at room temperature. The sample separated after evaporation from 20% water / methanol was analyzed by DSC and powder X-ray diffraction. The measured powder X-ray diffraction pattern of the polymorph of the compound having formula IA (designated as form A(b)) is shown in... Figure 4 As shown in the figure. The DSC trace of form A(b) is in Figure 5 As shown in the image.

[0254] 1c. Preparation of form A(h)

[0255] Another sample of the compound having formula IA was subjected to slow evaporation from a water / ethanol mixture. Crystallographic analysis revealed that water is bound in the structure – there are two water molecules and two compound molecules having formula IA in the asymmetric unit. The hydrate (named form A(h)) was analyzed by DSC and TGA, as well as powder X-ray diffraction and single-crystal X-ray diffraction. The powder X-ray diffraction pattern of the hydrate is shown in... Figure 6 The graph shown is a prediction from single-crystal intensity data. Figure 7 As shown in the image.

[0256] 1d. Preparation of Forms B(a) and C(a)

[0257] Compound samples with formulas IB and IC were prepared as follows: the sample was dissolved in acetone, the acetone was filtered through a 0.2 µm syringe filter into a clean vial, and the vial was placed in a fume hood to allow the acetone to evaporate. The resulting solid samples were analyzed by powder X-ray diffraction and DSC. The powder X-ray diffraction patterns for IB and IC are identical. The pattern for compounds with formula IB is shown in […]. Figure 8 The compound is shown in [the image]. The DSC of this compound is [data missing]. Figure 9 As shown in the image.

[0258] Crystals suitable for single-crystal X-ray diffraction analysis were grown in a mixture of isopropanol / water (80 / 20). The plots predicted from single-crystal intensity data are shown in... Figure 10 As shown in the image.

[0259] 1e. Preparation of racemic mixtures of compounds having formulas IA and ID

[0260] Equal amounts of compounds having formulas IA and ID were dissolved in acetone and then left at room temperature until the solvent evaporated. The resulting crystalline solids were characterized by powder X-ray diffraction and DSC. The measured powder X-ray diffraction patterns of the polymorphs of the racemic mixtures of compounds having formulas IA and ID are shown in [the diagram]. Figure 11 The DSC trace of this polymorph is shown in [the image]. Figure 12 As shown in the image.

[0261] 2. Analysis of polymorphs

[0262] After preparation, as detailed above, the samples were analyzed by powder X-ray diffraction and / or single-crystal X-ray diffraction and / or differential scanning calorimetry (DSC) and / or thermogravimetric analysis (TGA). The methods used for these analytical techniques are detailed below: Powder X-ray diffraction analysis of solid materials was performed using a Bruker D8 powder diffractometer at room temperature and relative humidity above 40%. The sample was mounted in a Perspex sample holder and flattened. The sample holder was rotated, and X-rays were collected from 4° to 34° 2-θ at scan times of 25 to 30 minutes (depending on the image intensity).

[0263] Single-crystal intensity data were collected using a graphite monochromator with Cu Kα radiation (λ = 1.5418 Å) on an Oxford Xcalibar PX super-diffractometer. The crystal was mounted in Paratone N oil at 100 K for data collection. The data were resolved using the CRYSTALS software package.

[0264] DSC was performed using a Mettler Toledo DSC1. Approximately 5 mg of sample was loaded and heated from 25°C to 160°C at a rate of 10°C / min. The lid of the DSC crucible was perforated to allow any gases generated during the heating of the sample to escape.

[0265] Raman spectroscopy was performed using a Thermo Scientific DXR Raman microscope: a 780 nM Raman laser was focused onto the sample on a quartz slide.

[0266] 3. Stability of polymorphs

[0267] The polymorph sample, named form A(c), was stirred in 5 ml of dimethyl carbonate for 2 days. The crystals were separated, air-dried, and characterized by DSC and pXRD. The DSC curve showed a sharp, single-melting endothermic melt with a melting peak at 141°C, and the pXRD plot matched that of form A(a), indicating that all forms A(c) had been converted to form (A)a.

[0268] Although the invention has been described with reference to its preferred embodiments and examples, the scope of the invention is not limited to those described embodiments. As will be appreciated by those skilled in the art, modifications and rewrites can be made to the above invention without departing from the spirit and scope of the invention, as defined and limited by the appended claims. For all purposes, all publications cited herein are incorporated herein by reference in their entirety, to the extent that each individual publication is specifically and individually indicated to be so incorporated by reference.

Claims

1. A crystalline polymorph form A(a) of a compound having formula IA. IA It has the following powder X-ray diffraction pattern, which includes at least three 2θ angle values ​​selected from the group consisting of: 6.0 ± 0.2, 8.8 ± 0.2, 9.4 ± 0.2, 10.1 ± 0.2, 11.9 ± 0.2, 14.5 ± 0.2, 15.9 ± 0.2, 20.2 ± 0.2, 20.7 ± 0.2, 21.2 ± 0.2, 21.7 ± 0.2, 22.1 ± 0.2 and 22.7 ± 0.

2.

2. The crystalline polymorph of claim 1, having a powder X-ray diffraction pattern comprising at least six 2θ angle values ​​selected from the group consisting of: 6.0 ± 0.2, 8.8 ± 0.2, 9.4 ± 0.2, 10.1 ± 0.2, 11.9 ± 0.2, 14.5 ± 0.2, 15.9 ± 0.2, 20.2 ± 0.2, 20.7 ± 0.2, 21.2 ± 0.2, 21.7 ± 0.2, 22.1 ± 0.2 and 22.7 ± 0.

2.

3. The crystalline polymorph as described in claim 1 or 2, having the following lattice parameters: a = 5.06 Å ± 0.01 Å, b = 18.92 Å ± 0.01 Å, c = 24.17 Å ± 0.01 Å, α = 90° ± 0.01°, β = 90° ± 0.01°, γ = 90° ± 0.01°, and volume = 2315 Å. 3 ± 1 Å 3 .

4. The crystalline polymorph as claimed in any one of claims 1 to 3, wherein the polymorph has a melting point of 141°C ± 2°C.

5. A composition comprising a crystalline polymorph as described in any one of claims 1 to 4.

6. The composition of claim 5, further comprising at least one agriculturally acceptable surfactant, carrier, or diluent.

7. The composition of claim 5, comprising more than one polymorph as defined in any one of claims 1 to 4.

8. The composition of claim 5, wherein the polymorph is rich in a polymorph of a compound having formula IA.

9. The composition of claim 8, wherein the polymorph is rich in the polymorphs defined in claims 1 to 4.

10. The composition according to any one of claims 5 to 9, wherein it comprises at least one additional insecticide or nematicide.

11. The composition of claim 10, wherein the additional insecticide or nematicide is selected from: acephate, acetamiprid, bifenthrin, fenitrothion, chlorantraniliprole, cyantraniliprole, difenoconazole, flonicamid, imidacloprid, indoxacarb, lambda-cyhalothrin, lufenuron, emamectin benzoate, acetamiprid, fipronil, methoxybenzoyl, flufenoxuron, thiamethoxam, spinosad, spinosad, and sulfadiazine.

12. The composition of claim 11, wherein the insecticide is selected from ethyl spinosad and spinosad.

13. The composition of claim 11, wherein the insecticide is spinosad.

14. The composition of claim 11, wherein the insecticide is spinosad.

15. The composition of claim 11, wherein the insecticide is selected from bromfenac, methoxybenzoyl, dimethomorph, and lufenuron.

16. The composition of claim 11, wherein the insecticide is bromfenac.

17. The composition of claim 11, wherein the insecticide is methoxybenzoyl.

18. The composition of claim 11, wherein the insecticide is buprofen.

19. The composition of claim 11, wherein the insecticide is lufenuron.

20. The composition of any one of claims 10 to 19, wherein the weight ratio of the polymorph to the insecticide or nematicide is between 1000:1 and 1:

100.

21. The composition of any one of claims 10 to 19, wherein the weight ratio of the polymorph to the insecticide or nematicide is between 500:1 and 1:

100.

22. The composition of any one of claims 10 to 19, wherein the weight ratio of the polymorph to the insecticide or nematicide is between 250:1 and 1:

66.

23. The composition of any one of claims 10 to 19, wherein the weight ratio of the polymorph to the insecticide or nematicide is between 125:1 and 1:

33.

24. The composition of any one of claims 10 to 19, wherein the weight ratio of the polymorph to the insecticide or nematicide is between 100:1 and 1:

25.

25. The composition of any one of claims 10 to 19, wherein the weight ratio of the polymorph to the insecticide or nematicide is between 66:1 and 1:

10.

26. The composition of any one of claims 10 to 19, wherein the weight ratio of the polymorph to the insecticide or nematicide is between 33:1 and 1:

5.

27. The composition of any one of claims 10 to 19, wherein the weight ratio of the polymorph to the insecticide or nematicide is between 8:1 and 1:

3.

28. A method for preventing or controlling insect infestation on plants or plant propagation material, the method comprising treating the plant or plant propagation material with an insecticidal effective amount of the composition as described in any one of claims 5 to 27.

29. The method of claim 28, used for the prevention or control of diamondback moth (Plutella xylostella), thrips species (Thrips spp.), aphids, spider mite species (Tetranychus spp.) and / or whitefly species (Bemisia spp.).

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