OA19869A - Polymorphs. - Google Patents
Polymorphs. Download PDFInfo
- Publication number
- OA19869A OA19869A OA1202000204 OA19869A OA 19869 A OA19869 A OA 19869A OA 1202000204 OA1202000204 OA 1202000204 OA 19869 A OA19869 A OA 19869A
- Authority
- OA
- OAPI
- Prior art keywords
- spp
- polymorph
- compound
- polymorphs
- formula
- Prior art date
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Abstract
The present invention relates to solid forms of the insecticide of formula (I): compositions comprising the solid forms and methods of their use as insecticides.
Description
This invention relates to solid forms of an isoxazoline dérivative, compositions comprising the solid forms and methods of their use as insecticides.
POLYMORPHS
WO 2011/067272 discloses that certain isoxazoline dérivatives hâve pesticidal activity, in particular, insecticidal, acaricidal, molluscicidal and nematicidal activity. In particular, a compound of formula I is disclosed:
Mixtures of this compound with other insecticides are disclosed in WO 2012/163960 and with fungicides in WO 2012/163945.
New solid forms of this compound and its isomers, their compositions and methods of their préparation and use hâve now been discovered.
There are four isomers of the compound of formula I: A, B, C and D, as shown below. The présent invention relates to polymorphie forms of ail of these isomers, in combination or in isolated form. ।
Accordingly, the présent invention relates to novel crystalline forms of the compound of formula IA, designated Form A(a). This crystalline polymorph Form A(a) may be 5 characterised 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.
TABLE 1
Class | Orthorhombic |
Space Group | P2i2i2i |
Cell Lengths (Â) | a = 5.06, b = 18.92, c = 24.17 |
Cell Angles (°) | α = 90, β = 90,γ = 90 |
Unit Cell Volume (A3) | 2315 |
Z | 4 |
In the table, a, b, c = Length of the edges of the unit cell; α, β , γ = Angles of the unit cell; and Z = molécules per cell.
Thus, in one embodiment of the présent invention, the crystalline polymorph | designated Form A(a) has the following lattice pararpeters: a=5.06 Â ± 0.01 Â, b=l 8.92 Â ± 0.01 Â, c=24.17 A ± 0.01 Â, a = 90° ± 0.01 °, β = 90° ± 0.01 °, γ = 90° ± 0.01 ° and volume = 2315Â3±1 A3.
The crystalline polymorph designated Form A(a) may also be characterised by a powder X-ray diffraction pattern expressed in terms of 20 angles or d spacings. Thus, in another embodiment of the invention, the crystalline polymorph has a powder X-ray diffraction pattern comprising at least three, at least six, or ail 20 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. These peak values, along with the corresponding d spacing values are shown in Table 2 below:
TABLE 2
2-Theta | D |
6.0 | 14.6 |
8.8 | 10.1 |
9.4 | 9.4 |
10.1 | 8.8 |
11.9 | 7.4 |
14.5 | 6.1 |
15.9 | 5.6 |
20.2 | 4.4 |
20.7 | 4.3 |
21.2 | 4.2 |
21.7 | 4.1 |
22.1 | 4.0 |
22.7 | 3.9 |
These 20 angle values are derived from a powder X-ray diffraction pattern of the polymorph obtained using the method of Example 1. The values are generated using an average wavelength of 1.54056Â with a 20 step size of 0.02°.
In another embodiment, the crystalline polymorph designated Form A(a) has a melting point of 141 °C ± 2°C. This melting point is obtained using Differential Scanning
Calorimetry (DSC) with a heating rate of 10°C/minute.
The crystalline polymorph designated Form A(a) may also be characterised by a Raman spectra expressed in terms of Raman shift (cm’1). Thus, in another embodiment of the invention, the crystalline polymorph has a Raman spectra comprising at least three, at least Lx, at least nine, at least twelve, at least fiftteen, or ail Aman shift values selected from 15 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 ft 2.
The invention also relates to a further novel crystalline form of the compound of formula IA, designated Form A(b) which may be characterised by a powder X-ray diffraction pattern expressed in terms of 20 angles or d spacings. This crystalline polymorph has a powder X-ray diffraction pattern comprising at least three 20 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 peak values, along with the corresponding d spacing values are shown in Table 3 below:
TABLE 3
2-Theta | D |
15.3 | 5.8 |
16.3 | 5.4 |
17.6 | 5.0 |
19.3 | 4.6 |
19.8 | 4.5 |
22.0 | 4.0 |
22.9 | 3.9 |
24.9 | 3.6 |
25.3 | 3.5 |
These 20 angle values are derived from a powder X-ray diffraction pattern of the polymorph obtained using the method of Example 1. The values are generated using an average wavelength of 1.54056Â with a 20 step size of 0.02°.
The crystalline polymorph designated Form A(b) has a melting point of 152 °C ± 2°C. This melting point is obtained using Differential Scanning Calorimetry (DSC) with a 10 heating rate of 10°C/minute.
The invention also relates to a further novel crystalline form of the compound of formula IA, designated Form A(h), which is a hydrate. This crystalline polymorph Form A(h) may be characterised 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.
I TABLE 4 '
Class | Monoclinic |
i Space Group | Ρ2ι 1 |
Cell Lengths (Â) | a = 8.03, b = 16.10, c =120.37 |
Cell Angles (°) | a = 90, β = 97.02, γ = 90 |
Unit Cell Volume (Â3) | 2615 |
Z | 2 |
In the table, a, b, c = Length of the edges of the unit cell; α, β , γ = Angles of the unit cell; and Z = molécules per cell.
Thus, in one embodiment of the présent invention, the crystalline polymorph designated Form A(h) has the following lattice parameters: a=8.03 Â ± 0.01 A, b=16.10 Â ±
0.01 Â, c=20.37 Â ± 0.01 Â, a = 90° ± 0.01 °, β = 97.02° ± 0.01 °, γ = 90° ± 0.01 ° and volume = 2615Â3 ± 1 A3.
The crystalline polymorph designated Form A(h) may also be characterised by a powder X-ray diffraction pattern expressed in terms of 20 angles or d spacings. Thus, in another embodiment of the invention, the crystalline polymorph has a powder X-ray diffraction pattern comprising at least three, at least six, or ail 20 angle values selected from the group consisting of 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 10 ± 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 peak values, along with the corresponding d spacing values are shown in Table 5 below:
TABLE 5
2-Theta | D |
4.4 . | 20 .2 |
7.0 | 12.6 |
8.7 | 10.1 |
10.3 | 8.6 |
11.0 | 8.0 |
12.4 | 7.1 |
12.7 | 7.0 |
13.3 | 6.7 |
14.1 | 6.3 |
15.9 | 5.6 |
17.1 | 5.2 |
18.6 | 4.8 |
19.0 | 4.7 |
, 19.6 | 4.5 |
These 20 angle values are derived from a powder X-ray diffraction pattern predicted using the single crystal intensity data of the polymorph obtained using the method of Example 1. The values are generated using an average wavelength of 1.54056A with a 20 step size of 0.02°.
Also described is a crystalline form of the compound of formula IA, designated Form 20 A(c) which may be characterized by a melting point of 127 °C ± 2°C. This melting point is obtained using Differential Scanning Calorimetry (DSC) with a heating rate of
10°C/minute.It is noted that the crystal forms of the compound of formula ID will hâve identical parameters to those of the compound of formula IA. Therefore, the présent invention also relates to novel crystalline forms of the compound of formula ID, which hâve the physical parameters listed above for the compound of formula IA.
The invention also relates to a novel crystalline form of the compound of formula IB, which may be characterised by a powder X-ray diffraction pattern expressed in terms of 2Θ angles or d spacings. This crystalline polymorph has a powder X-ray diffraction pattern comprising at least three 20 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 peak values, along with the corresponding d spacing values are shown in Table 6 below:
TABLE 6
2-Theta | D |
4.1 | 21.4 |
8.3 | 10.7 |
10.2 | 8.7 |
12.4 | 7.1 |
15.5 | 5.7 |
16.5 | 5.4 |
18.2 | 4.9 |
18.4 | 4.8 |
18.7 | 4.7 |
19.0 | 4.7 |
20.5 | 4.3 |
21.0 | 4.2 |
21.4 | 4.1 |
These 20 angle values ar|e derived from a powder X-ray diffraction pattern prediétcd using the single crystal intensity data of the polymorph obtained using the method of Example 1. The values are generated using an average wavelength of 1.54056Â with a 20 step size of 0.02°. |
The crystalline polymorph of the compound of formula IB has a melting point of 206 °C ± 2°C. This melting point is obtained using Differential Scarming Calorimetry (DSC) with a heating rate of 10°C/minute.
The invention also relates to a novel crystalline form of the compound of formula IC, which may be characterised by a powder X-ray diffraction pattern expressed in terms of 20 angles or d spacings. This crystalline polymorph has a powder X-ray diffraction pattern comprising at least three 2Θ angle values selected from the group consisting 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 peak values, along with the corresponding d spacing values are shown in Table 7 below. It is noted that the powder X-ray diffraction profile of the compound of formula IC is identical to that of the compound of formula IB.
TABLE 7
2-Theta | D |
4.1 | 21.4 |
8.3 | 10.7 |
10.2 | 8.7 |
12.4 | 7.1 |
15.5 | 5.7 |
16.5 | 5.4 |
18.2 | 4.9 |
18.4 | 4.8 |
18.7 | 4.7 |
19.0 | 4.7 |
20.5 | 4.3 |
21.0 | 4.2 |
21.4 | 4.1 |
These 20 angle values are derived from a powder X-ray diffraction pattern predicted 10 using the single crystal intensity data of the polymorph obtained using the method of
Example 1. The values are generated using an average wavelength of 1.54056Â with a 20 step size of 0.02°.
The crystalline polymorph of the compound of formula IC has a melting point of 206 °C ± 2°C. This melting point is obtained] using Differential Scanning Calorimetry (DSC) 15 with a heating rate of 10°C/minute.
The invention also relates to a further novel crystalline form of a racemate of the compounds of formula IA and formula ID, which may be characterised by a powder X-ray diffraction pattern expressed in terms of 20 angles or d spacings. This crystalline polymorph has a powder X-ray diffraction pattern comprising at least three 20 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 peak values, along with the corresponding d spacing values are shown in Table 8 below:
TABLE 8
2-Theta | D |
4.0 | 21.9 |
8.1 | 11.0 |
9.7 | 10.2 |
11.1 | 8.0 |
12.7 | 7.0 |
15.3 | 5.8 |
15.9 | 5.6 |
16.2 | 5.5 |
16.7 | 5.3 |
18.4 | 4.8 |
19.5 | 4.6 |
19.8 | 4.5 |
20.3 | 4.4 |
21.8 | . 4.1 |
23.9 | 3.7 |
These 2Θ angle values are derived from a powder X-ray diffraction pattern of the polymorph obtained using the method of Example 1. The values are generated using an average wavelength of 1.54056Â with a 20 step size of 0.02°.
The crystalline polymorph of the racemate of the compounds of formula IA and ID has a melting point of 173 °C ± 2°C. This melting point is obtained using Differential
Scanning Calorimetry (DSC) with a heating rate of 10°C/minute.
In the context of the présent invention, a polymorph is a particular crystal form of a | Chemical compound that can exist in more than or|e crystal form in the solid state. A crystal form of a compound contains the constituent molécules arranged in orderly repeating patterns extending in ail three spatial dimensions (in contrast, an amorphous solid form has
115 no long-range order in the position of molécules). Different polymorphe of a compound i hâve different arrangements of atoms and or molécules in their crystal structure. When the compound is a biologically active compound, such as an insecticide, the différence in crystal structures can lead to different polymorphs having differing Chemical, physical and biological properties. Properties which may be affected include crystal shape, density, hardness, colour, Chemical stability, melting point, hydroscopicity, suspensibility, dissolution rate and biological availability. As such, a spécifie polymorph may hâve properties which make it more advantageous in a particular use relative to another polymorph of the same compound: in particular, the physical, Chemical and biological properties listed above can hâve a significant effect on the development of production methods and formulations, the ease with which a compound can be combined in a formulation with other active ingrédients and formulation components and the quality and efficacy of plant treatment agents, such as insecticides. It is noted that predicting whether the solid state of a compound may be présent as more than one polymorph is not possible and nor is it possible to predict the properties of any of these crystal forms.
In particular, use of a spécifie polymorph may allow use of new formulations compared with existing polymorphic/amorphous forms of a compound. This might be advantageous for a number of reasons. For example, a suspension concentrate (SC) formulation may be preferred over an émulsion concentrate (EC) because the lack of solvent in the SC often means that the formulation is likely to be less phytotoxic than an équivalent EC formulation — however, if the existing form of a compound is not stable in such an SC formulations, polymorphie conversion might occur leading to unwanted crystal growth. Such crystal growth is detrimental because it leads to, for example, thickening and potentially solidification of the formulation which can lead to blockages in application equipment, e.g. in spray nozzles in agricultural application machinery. Using a stable polymorphie form would overcome these issues.
Assaying the solid phase for the presence of crystals may be carried out by conventional methods known in the art. For example, it is convenient and routine to use powder X-ray diffraction techniques. Other techniques which may be used include differential scanning calorimetry (DSC), thermogravimetric analysis (TGA) and Raman or Infra-red spectroscopy, NMR, gas chromatography or HPLC. Single crystal X-ray diffraction is especially useful in identifying crystal structures.
The polymorphs of the invention may be applied in unchanged form but are more preferably incorporated into agrochemical compositions bÿ conventional means. Accordingly, in a further aspect, the invention provides an'agrochemical composition comprising a polymorph of the invention as defined above and at least one agriculturally acceptable carrier or diluent.
In addition, compositions of the invention may comprise more than one polymorph of the invention. In particular, the compound of formula IA is more biologically active than the compounds of formulas IB, IC and ID. As such, whilst the compositions of the invention may contain a mixture of the compounds of IA, IB, IC and ID m the polymorphie forms disclosed herein or otherwise in any amounts, they may also be enriched for the compound of formata IA or a polymorph of the compound of formula IA. In particular, they may be enriched for the polymorph designated Form A(a). ‘Enriched’ means that the molar proportion of the compound or polymorph of formula IA compared to the total amount of the compounds of formula IA, IB, IC and ID is greater than 50%, e.g, at least 55, 60, 65, 70, 75, 80, 85, 90,95,96,97,98 or at least 99%.
The agrochemical compositions comprising the polymorph or polymorphs of the présent invention are preventively and/or curatively valuable active ingrédients in the field of pest control, even at low rates of application, hâve a favourable biocidal spectrum and are well tolerated by warm-blooded species, fish and plants. Compositions of the invention may act against ail or only individual developmental stages of normally sensitive, but also résistant, animal pests, such as insects or représentatives of the order Acarina. The insecticidal or acaricidal activity of the compositions can manifest itself directly, i. e. in destruction of the pests, which takes place either immediately or only after some time has elapsed, for example during ecdysis, or indirectly, for example in a reduced oviposition and/or hatching rate, a good activity corresponding to a destruction rate (mortality) of at least 50to60%.
As such, the agrochemical compositions comprising the polymorph or polymorphs of the présent invention can be used for the control of plant pathogenic insects on a number of plant species. Accordingly, the invention also provides a method of preventing or controliing insect infection on plants or plant propagation material comprising treating the plant or plant propagation material with an insecticidally effective amount of an agricultural compositioÀ of the invention. I
The term “insecticide” as used herein means a compound or composition that Controls or modifies the growth of insects. The term “insecticidally effective amount” means the quantité of such a compound or composition or a combination of such compounds or compositions that is capable of killing, controliing, or infecting insects, retarding the growth or reproduction of insects, reducing an insect population, and/or reducing damage to plants caused by insects.
n
By ‘plant propagation material’ is meant seeds of ail kinds (fruit, tubers, bulbs, grains etc.), cuttings, eut shoots and the like.
Examples of the abovementioned animal pests are:
from the order Acarina, for example, Acalitus spp, Aculus spp, Acaricalus spp, Aceria spp, Acarus siro, Amblyomma spp., Argas spp., Boophilus spp., Brevipalpus spp., Bryobia spp, Calipitrimerus spp., Chorioptes spp., Dermanyssus gallinae, Dermatophagoides spp, Eotetranychus spp, Eriophyes spp., Hemitarsonemus spp, Hyalomma spp., Ixodes spp., Olygonychus spp, Omithodoros spp., Polyphagotarsone latus, Panonychus spp., Phyllocoptruta oleivora, Phytonemus spp, Polyphagotarsonemus spp, Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Steneotarsonemus spp, Tarsonemus spp. and Tetranychus spp.', from the order Anoplura, for example, Haematopinus spp., Linognathus spp., Pediculus spp., Pemphigus spp. and Phylloxéra spp.', from the order Coleoptera, for example, Agriotes spp., Amphimallon majale, Anomala orientalis, Anthonomus spp., Aphodius spp, Astylus atromaculatus, Ataenius spp, Atomaria linearis, Chaetocnema tibialis, Cerotoma spp, Conoderus spp, Cosmopolites spp., Cotinîs nitida, Curculio spp., Cyclocephala spp, Dermestes spp., Diabrotica spp., Diloboderus abderus, Epilachna spp., Eremnus spp., Heteronychus arator, Hypothenemus hampei, Lagria vilosa, Leptinotarsa decemLineata, Lissorhoptrus spp., Liogenys spp, Maecolaspis spp, Maladera castanea, Megascelis spp, Melighetes aeneus, Melolontha spp., Myochrous armatus, Orycaephilus spp., Otiorhynchus spp., Phyllophaga spp, Phlyctinus spp., Popillia spp., Psylliodes spp., Rhyssomatus aubtilis, Rhizopertha spp., Scarabeidae, Sitophilus spp., Sitotroga spp., Somaticus spp, Sphenophorus spp, Stemechus subsignatus, Tenebrio spp., Tribolium spp. and Trogoderma spp.; I from the order Diptera, for example, Aedes spp., Anopheles spp, Antherigona soccata.Bactrocea oleae, Bibio hortulanus, Bradysia spp, Calliphora erythrqcephala, Ceratitis spp., Chrysomyia spp., Culex spp., Cuterebra spp., Dacus spp., Délia spp, Drosophila melanogaster, Fannia spp., Gastrophilus spp., 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 spp, Sciara spp., Stomoxys spp., Tabanus spp., Tannia spp. and Tipula spp.;
from the order Hemiptera, for example, Acanthocoris scabrator, Acrostemum spp,
Adelphocoris lineolatus, Amblypelta nitida, Bathycoelia thalassina, Blissus spp, Cimex spp.,
Clavigralla tomentosicollis, Creontiades spp, Distantiella theobroma, Dichelopsfurcatus, Dysdercus spp., Edessa spp, Euchistus spp., Eurydema pulchrum, Eurygaster spp., Halyomorpha halys, Horcias nobilellus, Leptocorisa spp., Lygus spp, Margarodes spp, Murgantia histrionic, Neomegalotomus spp, Nesidiocoris tenuis, Nezara spp., Nysius simulons, Oebalus insularis, Piesma spp., Piezodorus spp, Rhodnius spp., Sahlbergella sîngularis, Scaptocoris castanea, Scotinophara spp., Thyanta spp, Triatoma spp., and Vatiga illudens;
from the order Homoptera, for example, Acyrthosium pisum, Adalges spp, Agalliana ensigera, Agonoscena targionii, Aleurodicus spp, Aleurocanthus spp, Aleurolobus barodensis, Aleurothrixus floccosus.Aleyrodes brassicae, Amarasca biguttula, Amritodus atkinsoni, Aonidiella spp., Aonidiella auranti, Aphididae, Aphis spp., Aspidiotus spp., Aulacorthum solani, Bactericera cockerelli, Bemisia spp, Brachycaudus spp, Brevicoryne brassicae, Cacopsylla spp, Cavariella aegopodii Scop., Ceroplaster spp., Chrysomphalus aonidium, Chrysomphalus dictyospermi, Cicadella spp, Cofana spectra, Cryptomyzus spp, Cicadulina spp, Coccus hesperidum, Dalbulus maidis, Dialeurodes spp, Diaphorina citri, Diuraphis noxia, Dysaphis spp, Empoasca spp., Eriosoma larigerum, Erythroneura spp., Gascardia spp., Glycaspis brimblecombei, Hyadaphis pseudobrassicae, Hyalopterus spp, Hyperomyzus pallidus, Idioscopus clypealis, Jacobiasca lybica, Laodelphax spp., Lecanium comi, Lepidosaphes spp., Lopaphis erysimi, Lyogenys maidis, Macrosiphum spp., Mahanarva spp, Metcalfa pruinosa, Metopolophium dirhodum, Myndus crudus, Myzus spp., Neotoxoptera sp, Nephotettix spp., Nilaparvata spp., Nippolachnus piri Mats, Odonaspis ruthae, Oregma lanigera Zehnter, Parabemisia myricae, Paratrioza cockerelli, Parlatoria spp., Pemphigus spp., Peregr^nus maidis, Perkinsiella spp, Phorodon humuli, Phylloxéra spp, Planococcus spp., Pseudaulacaspis spp., Pseudococcus spp., Pseudatomoscelis seriatus, Psylla spp., Pulvinaria aethiopica, Quadraspidiotus spp., Quesada gigas, Recilia dorsalis, Rhopalosiphum spp., Saissetia spp., Scaphoideus spp., Schizaphis spp., Sitobion spp., Sogatella furcifera, SpissistiÙis festinus, Tarophagus Proserpina, Toxoptera spp, Trialeurodes spp, Tridiscus sporoboli, Trionymus spp, Trioza erytreae, Unaspis citri, Zygina flammigera, and Zyginidia scutellaris-, from the order Hymenoptera, for example, Acromyrmex, Arge spp, Atta spp., Cephus spp., Diprion spp., Diprionidae, Gilpinia polytoma, Hoplocampa spp., Lasius spp.,
Monomorium pharaonis, Neodiprion spp., Pogonomyrmex spp, Slenopsis invicta, Solenopsis spp. and Vespa spp.;
from the order Isoptera, for example, Coptotermes spp, Co mi ternes cumulons, Incisitermes spp, Macrotermes spp, Mastotermes spp, Microtermes spp, Reticulitermes spp.;
Solenopsis geminate; .
from the order Lepidoptera, for example, Acleris spp., Adoxophyes spp., Aegeria spp., Agrotis spp., Alabama argillaceae, Amylois spp., Anticarsia gemmatalis, Archips spp., Argyresthia spp, Argyrotaenia spp., Autographa spp., Bucculatrix thurberiella, Busseola fusca, Cadra cautella, Carposina nipponensis, Chilo spp., Choristoneura spp.,
Chrysoteuchia topiaria, Clysia ambiguella, Cnaphalocrocis spp., Cnephasia spp., Cochylis spp., Coleophora spp., Colias lesbia, Cosmophila flava, Crambus spp, Crocidolomia binotalis, Cryptophlebia leucotreta, Cydalima perspectalis, Cydia spp., Diaphania perspectalis, Diatraea spp., Diparopsis castanea, Earias spp., Eldana saccharina, Ephestia spp., Epinotia spp, Estigmene acrea, Etiella zinckinella, Eucosma spp., Eupoecilia ambiguella, Euproctis spp., Euxoa spp., Feltia jaculiferia, Grapholita spp., Hedya nubiferana, Heliothis spp., Hellula undalis, Herpetogramma spp, Hyphantria cunea, Keiferia lycopersicella, Lasmopalpus lignosellus, Leucoptera scitella, Lithocollethis spp., Lobesia botrana, Loxostege bifidalis, Lymantria spp., Lyonetia spp., Malacosoma spp., Mamestra brassicae, Manduca sexta, Mythimna spp, Noctua spp, Operophtera spp.,
Omiodes indica, Ostrinia nubilalis, Pammene spp., Pandemis spp., Panolisflammea, Papaipema nebris, Pectinophora gossypiela, Perileucoptera cqffeella, Pseudaletia unipuncta, Phthorimaea operculella, Pieris rapae, Pieris spp., Plutella xylostella, Prays spp., Pseudoplusia spp, Rachiplusia nu, Richia albicosta, Scirpophaga spp., Sesamia spp., Sparganothis spp., Spodoptera spp., Sylepta derogate, Synanthedon spp., Thaumetopoea spp., Tortrix spp., Trichoplusia ni, Tu^a absoluta, and Yponomeuta spp.’, from the order Mallophaga, for example, Damalinea spp. and Trichodectes spp.;
from the order Orthoptera, fo^example, Blatta spp., Blattella spp., Gryllotalpa spp., Leucophaea maderae, Locusta spp., Neocurtilla hexadactyla, Periplaneta spp., Scapteriscus spp, and Schistocerca spp.·, from the order Psocoptera, for example, Liposcelis spp.·, from the order Siphonaptera, for example, Ceratophyllus spp., Ctenocephalides spp.
and Xenopsylla cheopis;
from the order Thysanoptera, for example, Calliothrips phaseoli, Frankliniella spp., Heliothrips spp, Hercinothrips spp., Parthenothrips spp, Scirtothrips aurantii, Sericothrips variabilis, Taeniothrips spp., Thrips spp; and/or from the order Thysanura, for example, Lepisma saccharina.
Examples of soil-inhabiting pests, which can damage a crop in the early stages of plant development, are:
from the order Lepidoptera, for example, Acleris spp., Aegeria spp., Agrotis spp.,
Alabama argillaceae, Amylois spp., Autographa spp., Busseolafusca, Cadra cautella, Chilo spp., Crocidolomia binotalis, Diatraea spp., Diparopsis castanea, Elasmopalpus spp., Heliothis spp., Mamestra brassicae, Phthorimaea operculella, Plutellaxylostella, Scirpophaga spp., Sesamia spp., Spodoptera spp. and Tortrix spp. ;
from the order Coleoptera, for example, Agriotes spp., Anthonomus spp., Atomaria 15 linearis, Chaetocnema tibialis, Conotrachelus spp., Cosmopolites spp., Curculio spp., Dermestes spp., Diabrotica spp., Dilopoderus spp., Epilachna spp., Eremnus spp., Heteronychus spp., Lissorhoptrus spp., Melolontha spp., Orycaephilusspp., Otiorhynchus spp., Phlyctinus spp., Popillia spp., Psylliodes spp., Rhizopertha spp., Scarabeidae, Sitotroga spp., Somaticus spp., Tanymecus spp., Tenebrio spp., Tribolium spp., Trogoderma spp. and
Zabrus spp.;
from the order Orthoptera, for example, Gryllotalpa spp.;
from the order Isoptera, for example, Reticulitermes spp. ;
from the order Psocoptera, for example, Liposcelis spp.;
from the order Anoplura, for example, Haematopinus spp., Linognathus spp., 25 Pediculus spp., Pemphigus spp. and Phylloxerà spp. ;
from the order Homoptera, for example, Eriosoma larigerum;
from the order Hymenoptera, for example, Acromyrmex, Atta spp., Cephus spp., Lasius spp., Monomoriumpharaonis, Neodiprion spp., Solenopsis spp. and Vespa spp.;
from the order Diptera, for example, Tipula spp.·, crucifer flea beetles (Phyllotreta spp.), root maggots (Délia spp.), cabbage seedpod weevil (Ceutorhynchus spp.) and aphids.
The compositions of the invention may also be useful for the control of nematodes. As such, the agrochemical compositions comprising the polymorph of the présent invention can be used for the control of plant pathogenic nematodes on a number of plant species. Accordingly, the invention also provides a method of controlling damage to plant and parts thereof by plant parasitic nematodes (Endoparasitic-, Semiendoparasitic- and Ectoparasitic nematodes), the method comprising treating the plant or plant propagation material with a nematicidally effective amount of an agricultural composition of the invention.
The term “nematicide” as used herein means a compound or composition that Controls or modifies the growth of nematodes. The term “nematicidally effective amount” means the quantity of such a compound or composition or a combination of such compounds or compositions that is capable of killing, controlling, or infecting nematodes, retarding the growth or reproduction of nematodes, reducing a nematode population, and/or reducing damage to plants caused by nematodes.
Examples of the abovementioned plant parasitic nematodes are:
root knot nematodes, Meloidogyne hapla, Meloidogyne incognito, Meloidogyne javanica, Meloidogyne arenaria and other Meloidogyne species; cyst-forming nematodes, Globodera rostochiensis and other Glohodera species; Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii, and other Heterodera species; Seed gall nematodes, Anguina species; Stem and foliar nematodes, Aphelenchoides species; Sting pematodes, Eelonolaimus longicaudatus and other Belonolaimus species; Pine nematodes, Bursaphelenchus xylophilus and other Bursaphelenchus species; Ring nematodes, Criconema species, Criconemella species, Criconemoides species, Mesocriconema species; Stem and bulb nematodes, Ditylenchus destructor, Ditylenchus dipsaci and other Ditylenchus species; Awl nematodes, Dolichodorus species; Spiral nematodes, Heliocotylenchus multicinctus and other Helicotylenchus species; Sheath and sheathoid nematodes, Hemicycliophora species and Hemicriconemoides species; Hirshmanniella species; Lance nematodes, Hoploaimus species; false rootknot nematodes, Nacobbus species; Needle nematodes, Longidorus elongatus and other Longidorus species; Pin nematodes, Pratylenchus species; Lésion nematodes, Pratylenchus neglectus, Pratylenchus pénétrons,
Pratylenchus curvitatus, Pratylenchus goodeyi and other Pratylenchus species; Burrowing nematodes, Radopholus similis and other Radopholus species; Reniform nematodes, Rotylenchus robustus, Rotylenchus reniformis and other Rotylenchus species; Scutellonema species; Stubby root nematodes, Trichodorus primitivus and other Trichodorus species, Paratrichodorus species; Stunt nematodes, Tylenchorhynchus claytoni, Tylenchorhynchus dubius and other Tylenchorhynchus species; Citrus nematodes, Tylenchulus species; Dagger nematodes, Xiphinema species; and other plant parasitic nematode species, such as Subanguina., spp Hypsoperine spp., Macroposthonia spp., Melinius spp., Punctodera spp., and Quinisuldus spp..
In particular, the nematode species Meloidogyne spp., Heterodera spp., Rotylenchus spp. and Pratylenchus spp. can be controlled by the compositions of the invention.
The compositions according to the invention can be used for controlling, i. e. containing or destroying, pests of the abovementioned type which occur in particular on plants, especially on useful plants and omamentals in agriculture, in horticulture and in forests, or on organs, such as fruits, flowers, foliage, stalks, tubers or roots, of such plants, and in some cases even plant organs which are formed at a later point in time remain protected against these pests.
Suitable target crops are, in particular, cereals, such as wheat, barley, rye, oats, rice, maize or sorghum; beet, such as sugar or fodder beet; fruit, for example pomaceous fruit, stone fruit or soft fruit, such as apples, pears, plums, peaches, almonds, cherries or berries, for example strawberries, raspberries or blackberries; leguminous crops, such as beans, lentils, peas or soya; oil crops, such as oilseed râpe, mustard, poppies, olives, sunflowers, coconut, castor, cocoa or ground nuts; cucurbits, such as pumpkins, cucumbers or melons; fibre plants, such as cotton, flax, hemp or jute; citrus fruit, such a^ oranges, lemons, grapefruit or tangerines; vegetables, such as spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes or bell peppers; Lauraceae, such as avocado, Cinnamonium or camphor; and also tobacco, nuts, coffee, eggplants, sugarcane, tea, pepper, grapevines, hops, the plantain family and latex plants. I
The compositions and/or methods of the présent invention may be also used on any omamental and/or vegetable crops, including flowers, shrubs, broad-leaved trees and evergreens.
For example the invention may be used on any of the following omamental species:
Agératum spp., Alonsoa spp., Anemone spp., Anisodontea capsenisis, Anthémis spp., Antirrhinum spp., Aster spp., Bégonia spp. (e.g. B. elatior, B. semperflorens, B. tubéreux), Bougainvillea spp., Brachycome spp., Brassica spp. (omamental), Calceolaria spp., Capsicum annuum, Catharanthus roseus, Canna spp., Centaurea spp., Chrysanthemum spp., Cineraria spp. (C. maritime), Coreopsis spp., Crassula coccinea, Cuphea ignea, Dahlia spp., Delphinium spp., Dicentra spectabilis, Dorotheantus spp., Eustoma grandiflorum, Forsythia spp., Fuchsia spp., Géranium gnaphalium, Gerbera spp., Gomphrena globosa, Heliotropium spp., Helianthus spp., Hibiscus spp., Hortensia spp., Hydrangea spp., Hypoestes phyllostachya, Impatiens spp. (I. Walleriana), Iresines spp., Kalanchoe spp., Lantana camara, Lavatera trimestris, Leonotis leonurus, Lilium spp., Mesembryanthemum spp., Mimulus spp., Monarda spp., Nemesia spp., Tagetes spp., Dianthus spp. (carnation), Canna spp., Oxalis spp., Bellis spp., Pélargonium spp. (P. peltatum, P. Zonale), Viola spp. (pansy), Pétunia spp., Phlox spp., Plecthranthus spp., Poinsettia spp., Parthenocissus spp. (P. quinquefolia, P. tricuspidata), Primula spp., Ranunculus spp., Rhododendron spp., Rosa spp. (rose), Rudbeckia spp., Saintpaulia spp., Salvia spp., Scaevola aemola, Schizanthus wisetonensis, Sedum spp., Solanum spp., Surfinia spp., Tagetes spp., Nicotinia spp., Verbena spp., Zinnia spp. and other bedding plants.
For example the invention may be used on any of the following vegetable species: Allium spp. (A. sativum, A., cepa, A. oschaninii, A. Porrum, A. ascalonicum, A. fistulosum), Anthriscus cerefolium, Apium graveolus, Asparagus ojjïcinalis, Beta vulgarus, Brassica spp. (B. Oleracea, B. Pekinensis, B. rapa), Capsicum annuum, Cicer arietinum, Cichorium endivia, Cichorum spp. (C. intybus, C. endivia), Citrillus lanatus, Cucumis spp. (C. sativus, C. melo), Cucurbita spp. (C. pepo, C. maxima), Cyanara spp. (C. scolymus, C. cardunculus), Daucus carota, Foeniculum vulgare, Hypericum spp., Lactiica sativa, Lycopersicon spp. (L. esculentum, L. lycopersicum), Mentha spp., Ocimum basilicum, Petroselinum crispum, Phaseolus spp. (P. vulgaris, P. coccineus), Pisum sativum, Raphanus sativus, Rheum rhaponticum, Rosemarinus spp., Salvia spp., Scorzonera lïispanica, Solanum melongena, Spinacea oleracea, Valerianella spp. (V. locusta, V. eriocarpa) and Vicia faba.
Preferred omamental species include African violet, Bégonia, Dahlia, Gerbera, Hydrangea, Verbena, Rosa, Kalanchoe, Poinsettia, Aster, Centaurea, Coreopsis, Delphinium, Monarda, Phlox, Rudbeckia, Sedum, Pétunia, Viola, Impatiens, Géranium,
Chrysanthemum, Ranunculus, Fuchsia, Salvia, Hortensia, rosemary, sage, St. Johnswort, mint, sweet pepper, tomato and cucumber.
The polymorphs according to the invention are especially suitable for controlling Aphis craccivora, Diabrotica balteata, Heliothis virescens, Myzus persicae, Plutella xylostella and Spodoptera littoralis in cotton, vegetable, maize, rice and soya crops. The polymorphs according to the invention are further especially suitable for controlling Mamestra (preferably in vegetables), Cydia pomonella (preferably in apples), Empoasca(preferably in vegetables, vineyards), Leptinotarsa (preferably in potatos) and Chilo supressalis (preferably in rice).
Crops are to be understood as being those which are naturally occurring, obtained by conventional methods of breeding, or obtained by genetic engineering. They include crops which contain so-called output traits (e.g. improved storage stability, higher nutritional value and improved flavour).
Crops are to be understood as also including those crops which hâve been rendered tolérant to herbicides like bromoxynil or classes of herbicides such as ALS-, EPSPS-, GS-, HPPD- and PPO-inhibitors. An example of a crop that has been rendered tolérant to imidazolinones, e.g. imazamox, by conventional methods of breeding is Clearfield® summer canola. Examples of crops that hâve been rendered tolérant to herbicides by genetic engineering methods include e.g. glyphosate- and glufosinate-resistant maize varieties commercially available under the trade names RoundupReady®, Herculex I® and LibertyLink®.
Crops are also to be understood as being those which naturally are or hâve been rendered résistant to harmful insects. This includes plants transformed by the use of recombinant DNA techniques, for example, to be capable of synthesising one or mi)rc selectively acting toxins, such as are known, for example, from toxin-producing bacteria. Examples of toxins which can be expressed include δ-endotoxins, végétative insecticidal proteins (Vip), insecticidal proteins of bacteria colonising nematodes, and toxins produced by scorpions, arachnids, wasps and fungi.
An example of a crop that has been modified to express the Bacillus thuringiensis toxin is the Bt maize KnockOut® (Syngenta Seeds). An example of a crop comprising more than one gene that codes for insecticidal résistance and thus expresses more than one toxin is VipCot® (Syngenta Seeds). Crops or seed material thereof can also be résistant to multiple types of pests (so-called stacked transgenic events when created by genetic modification).
For example, a plant can hâve the ability to express an insecticidal protein while at the same time being herbicide tolérant, for example Herculex I® (Dow AgroSciences, Pioneer HiBred International).
Further areas of use of the compositions according to the invention are the protection of stored goods and store rooms and the protection of raw materials, such as wood, textiles, floor coverings or buildings, and also in the hygiene sector, especially the protection of humans, domestic animais and productive livestock against pests of the mentioned type.
The présent 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 comprises applying the compositions of the invention to the target pests, to their locus or to a surface or substrate by brushing, rolling, spraying, spreading or dipping. By way of example, an 1RS (indoor residual spraying) application of a surface such as a wall, ceiling or floor surface is contemplated by the method of the invention. In another embodiment, it is contemplated to apply such compositions to a suhstrate such as non-woven or a fabric material in the form of (or which can be used in the manufacture of) netting, clothing, bedding, curtains and tents. A further object of the invention is therefore a substrate selected from nonwoven and fabric material comprising a composition which contains a compound of formula (I).
In one embodiment, the method for controlling such pests comprises applying a pesticidally effective amount of the compositions of the invention to the target pests, to their locus, or to a surface or substrate so as to provide effective residual pesticidal activity on the surface or suhstrate. Such application may be made by brushing, rolling, spraying, spreading or dipping the pesticidal compositiojn of the invention. By way of example, an 1RS | application of a surface such as a wall, ceiling or floor surface is contemplated by the method of the invention so as to provide effective residual pesticidal activity on the surface. In another embodiment, it is contemplated to apply such compositions for residual control of pests on a substrate such as a fabric imaterial in the form of (or which can be used in the manufacture of) netting, clothing, bedding, curtains and tents.
Substrates including non-woven, fabrics or netting to be treated may be made of natural fibres such as cotton, rafifia, jute, flax, sisal, hessian, or wool, or synthetic fibres such as polyamide, polyester, polypropylene, polyacrylonitrile or the like. The polyesters are particularly suitable. The methods of textile treatment are known, e.g. WO 2008/151984,
WO 2003/034823, US 5631072, WO 2005/64072, WO 2006/128870, EP 1724392,
WO2005113886 or WO 2007/090739.
Further areas of use of the compositions according to the invention are the field of tree 5 injection/trunk treatment for ail omamental trees as well ail sort of fruit and nut trees.
In the field of tree injection/trunk treatment, the polymorphs according to the présent invention are especially suitable against wood-boring insects from the order Lepidoptera as mentioned above and from the order Coleoptera, especially against woodborers listed in the following tables A and B:
Table A. Examples of exotic woodborers of économie importance.
Family | Species | Host or Crop Infested |
Buprestidae | Agrilus planipennis | Ash |
Cerambycidae | Anoplura glabripennis | Hardwoods |
Scolytidae | Xylosandrus crassiusculus | Hardwoods |
X. mutilatus | Hardwoods | |
Tomicus piniperda | Conifers |
Table B. Examples of native woodborers of économie importance.
Family | Species | Host or Crop Infested |
Buprestidae | Agrilus anxius | Birch |
Agrilus politus | Willow, Maple | |
Agrilus sayi | Bayberry, Sweetfem | |
Agrilus vittaticolllis | Apple, Pear, Cranberry, । Serviceberry, Hawthom | |
Chrysobothris femorata | Apple, Apricot, Beech, Boxelder, Cherry, Chestnut, Curranît, Elm, Hawthom, Hackberry, HÏckory, Horsechestnut, Linden, Maple, Mountain-ash, Oak, Pecan, Pear, Peach, Persimmon, Plum, Poplar, |
Family | Species | Host or Crop Infested |
Quince, Redbud, Serviceberry, Sycamore, Walnut, Willow | ||
Texania campestris | Basswood, Beech, Maple, Oak, Sycamore, Willow, Yellow-poplar | |
Cerambycidae | Goes pulverulentus | Beech, Elm, Nuttall, Willow, Black oak, Cherrybark oak, Water oak, Sycamore |
Goes tigrinus | Oak | |
Neoclytus acuminatus | Ash, Hickory, Oak, Walnut, Birch, Beech, Maple, Eastem hophombeam, Dogwood, Persimmon, Redbud, Holly, Hackberry, Black locust, Honeylocust, Yellow-poplar, Chestnut, Osage-orange, Sassafras, Lilac, Mountainmahogany, Pear, Cherry, Plum, Peach, Apple, Elm, Basswood, Sweetgum | |
Neoptychodes trilineatus | Fig, Aider, Mulberry, Willow, Netleaf hackberry | |
Oberea ocellata | Sumac, Apple, Peach, Plum, Pear, Currant, Blackberry | |
Oberea tripunctata | Dogwood, Vibumum, Elm, । Sourwood, Blueberry, Rhododendron, Azalea, Laurel, Poplar, Willow, Mulberry | | |
Oncideres cingulata | Hickory, Pecan, Persimmon, Elm,l Sourwood, Basswood, Honeylocust, Dogwood, Eucalyptus, Oak, Hackberry, Maple, Fruit trees |
Family | Species | Host or Crop Infested |
Saperda calcarata | Poplar | |
Strophiona nitens | Chestnut, Oak, Hickory, Walnut, Beech, Maple | |
Scolytidae | Corthylus columbianus | Maple, Oak, Yellow-poplar, Beech, Boxelder, Sycamore, Birch, Basswood, Chestnut, Ehn |
Dendroctonus frontalis | Fine | |
Dryocoetes betulae | Birch, Sweetgum, Wild cherry, Beech, Pear | |
Monarthrum fasciatum | Oak, Maple, Birch, Chestnut, Sweetgum, Blackgum, Poplar, Hickory, Mimosa, Apple, Peach, Pine | |
Phloeotribus liminaris | Peach, Cherry, Plum, Black cherry, Elm, Mulberry, Mountainash | |
Pseudopityophthorus pruinosus | Oak, American beech, Black cherry, Chickasaw plum, Chestnut, Maple, Hickory, Hombeam, Hophombeam | |
Sesiidae | Paranthrene simulons | Oak, American chestnut |
Sannina uroceriformis | Persimmon | |
Synanthedon exitiosa 1 | Peach, Plum, Nectarine, Cherry, Apricot, Almond, Black cherry | |
Synanthedon pictipes | Peach, Plum, Cherry, Beach, Black Cherry | |
Synanthedon rubrofdscia | Tupelo | |
Synanthedon scitula 1 | Dogwood, Pecan, Hickory, Oak, Chestnut, Beech, Birch, Black cherry, Elm, Mountain-ash, Vibumum, Willow, Apple, Loquat, Ninebark, Bayberry |
Family | Species | Host or Crop Infested |
Vitacea polistiformis | Grape |
The présent invention may be also used to control any insect pests that may be présent in turfgrass, including for example beetles, caterpillars, tire ants, ground pearls, millipedes, sow bugs, mites, mole crickets, scales, mealybugs ticks, spittlebugs, southem chinch bugs and white grubs. The présent invention may be used to control insect pests at various stages of their life cycle, including eggs, larvae, nymphs and adults.
In particular, the présent invention may be used to control insect pests that feed on the roots of turfgrass including white grubs (such as Cyclocephala spp. (e.g. masked chafer, C. lurida), Rhizotrogus spp. (e.g. European chafer, R. majalis), Cotinus spp. (e.g. Green June beetle, C. nitida), Popillia spp. (e.g. Japanese beetle, P.japonica), Phyllophaga spp. (e.g. May/June beetle), Ataenius spp. (e.g. Black turfgrass ataenius, A. spretulus), Maladera spp. (e.g. Asiatic garden beetle, M. castanea) and Tomarus spp.), ground pearls (Margarodes spp.), mole crickets (tawny, southem, and short-winged; Scapteriscus spp., Gryllotalpa africana) and leatherjackets (European crâne fly, Tipula spp.).
The présent invention may also be used to control insect pests of turfgrass that are thatch dwelling, including armyworms (such as fall armyworm Spodoptera frugiperda, and common armywormPseudaletia unipuncta), cutworms, billbugs (Sphenophorus spp., such as S. venatus verstitus and S. parvulus), and sod webworms (such as Crambus spp. and the tropical sod webworm, Herpetogramma phaeopteralis).
The présent invention may also be used to control insect pests of turfgrass that live above the ground and feed on the turfgrass leaves, including chinch bugs (such as southem chinch bugs, Blissus insularis), Bermudagrass njiite (Eriophyes cynodoniensis), rhodesgrass mealybug (Antonina graminis), two-lined spittlebug (Propsapia bicincta), leafhoppers, cutworms (Noctuidae family) and greenbugs.
The présent invention may also be used toj control other pests of turfgrass such as red imported lire ants (Solenopsis invicta) that create ant mounds in turf.
In the hygiene sector, the compositions according to the invention are active against ectoparasites such as hard ticks, soft ticks, mange mites, harvest mites, Aies (biting and licking), parasitic fly larvae, lice, hair lice, bird lice and fleas.
Examples of such parasites are:
Of the order Anoplurida: Haematopinus spp., Linognathus spp., Pediculus spp. and
Phtirus spp., Solenopotes spp..
Of the order Mallophagida: Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Wemeckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp. and Felicola spp..
Of the order Diptera and the suborders Nematocerina and Brachycerina, for example Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp. and Melophagus spp..
Of the order Siphonapterida, for example Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp..
Of the order Heteropterida, for example Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp..
Of the order Blattarida, for example Blatta orientalis, Periplaneta americana, Blattelagermanica and Supella spp..
Of the subclass Acaria (Acarida) and the orders Meta- and Meso-stigmata, for example Argas spp., Omithodorus spp., Otobius spp., Ixodes spp., Amblyomma spp., Boophilus spp., Ij)ermacentor spp., Haemophysalis spp., Hyalomma spp.,|Rhipicephalus spp., Dermanyssus spp., Raillietia spp., Pneumonyssus spp., Stemostoma spp. and Varroa spp..
Of the orders Actinedida (Prostigmata) and Acaridida (Astigmata), for example
Àcarapis spp., Cheyletiella spp., Omithocheyletia spp., Myobia spp., Psorergatesspp.,
Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp.,
Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp.,
Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp. and
Laminosioptes spp..
The compositions according to the invention are also suitable for protecting against insect infestation in the case of materials such as wood, textiles, plastics, adhesives, glues, paints, paper and card, leather, floor coverings and buildmgs.
The compositions according to the invention can be used, for example, against the following pests: beetles such as Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Ptilinuspecticomis, Dendrobium pertinex, Emobius mollis, Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctus planicollis, Lyctus linearis, Lyctus pubescens, Trogoxylon aequale, Minthesrugicollis, Xyleborus spec.,Tryptodendron spec., Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec. and Dinoderus minutus, and also hymenopterans such as Sirex juvencus, Urocerus gigas, Urocerus gigas taignus and Urocerus augur, and termites such as Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis and Coptotermes formosanus, and bristletails such as Lepisma saccharina.
The rate at which the agrochemical compositions of the invention are applied will dépend upon the particular type of insect etc. to be controlled, the degree of control required and the timing and method of application and can be readily determined by the person skilled in the art. In general, the compositions of the invention can be applied at an application rate of between 0.005 kilograms/hectare (kg/ha) and about 5.0kg/ha, based on the total amount of active ingrédient (wherein ‘active ingrédient’ means the polymorph or polymorphs ofthe invention) in the composition. An application rate of between about O.lkg/ha and about 1.5kg/ha is preferred, with an application rate of between about 0.3kg/ha and 0.8kg/ha being especially preferred.
I I
In practice, the agrochemical compositions comprising the polymorph or polymorphs of the invention are applied as a formulation containing the various adjuvants and carriers known to or used in the industry.
These formulations can be in various physical forms, e.g. in the form of dusting powders, gels, wettable powders, water-dispersible granules, water-dispersible tablets, effervescent pellets, emulsifiable concentrâtes, microemulsifiable concentrâtes, oil-in-water émulsions, oil-flowables, aqueous dispersions, oily dispersions, suspo-emulsions, capsule suspensions, emulsifiable granules, soluble liquids, water-soluble concentrâtes (with water or a water-miscible organic solvent as carrier), impregnated polymer films or in other forms known e.g. from the Manual on Development and Use of FAO and WHO Spécifications for Pesticides, United Nations, First Edition, Second Révision (2010). Such formulations can either be used directly or diluted prior to use. The dilutions can be made, for example, with water, liquid fertilisers, micronutrients, biological organisms, oil or solvents.
The formulations can be prepared e.g. by mixing the polymorph or polymorphs (‘active ingrédient’) with the formulation adjuvants in order to obtain formulations in the form of finely divided solids, granules, solutions, dispersions or émulsions. The active ingrédient can also be formulated with other adjuvants, such as finely divided solids, minerai oils, oils of vegetable or animal origin, modified oils of vegetable or animal origin, organic solvents, water, surface-active substances or combinations thereof.
The active ingrédient can also be contained in very fine microcapsules. Microcapsules contain the active ingrédient in a porous carrier. This enables the active ingrédient to be released into the environment in controlled amounts (e.g. slow-release). Microcapsules usually hâve a diameter of from 0.1 to 500 microns. They contain the active ingrédient in an amount of about from 25 to 95 % by weight of the capsule weight. The active ingrédient can be in the form of a monolithic solid, in the form of fine particles in solid or liquid dispersion or in the form of a suitable solution. The encapsulating membranes can comprise, for example, natural or synthetic rubbers, cellulose, styrene/butadiene copolymers, polyacrylonitrile, polyacrylate, polyesters, polyamides, polyureas, polyuréthane or chemically modified polymers and starch xanthates or other polymers that are known to the person skilled in the art. Alternatively, very fine microcapsules can be formed in which the active ingrédient is contained in the form of finely divided particles in a solid matrix of base substance, but the microcapsules are not themselves encapsulated.
The formulation adjuvants that are suitable for the préparation of the formulations according to the invention are known per se. As liquid carriers there may be used: water, toluene, xylene, petroleum ether, vegetable oils, acetone, methyl ethyl ketone, cyclohexanone, acid anhydrides, acetonitrile, acetophenone, amyl acetate, 2-butanonc, butylène carbonate, chlorobenzene, cyclohexane, cyclohexanol, alkyl esters of acetic acid, diacetone alcohol, 1,2-dichloropropane, diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycol abietate, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, ΛζΎ-dimethylformamide, dimethyl sulfoxide, 1,4-dioxane, dipropylene glycol, dipropylene glycol methyl ether, dipropylene glycol dibenzoate, diproxitol, alkylpyrrolidone, ethyl acetate, 2-ethylhexanol, ethylene carbonate, 1,1,1trichloroethane, 2-heptanone, alpha-pmene, d-limonene, ethyl lactate, ethylene glycol, ethylene glycol butyl ether, ethylene glycol methyl ether, gamma-butyrolactone, glycerol, glycerol acetate, glycerol diacetate, glycerol triacetate, hexadecane, hexylene glycol, isoamyl acetate, isobomyl acetate, isooctane, isophorone, isopropylbenzene, isopropyl myristate, lactic acid, laurylamine, mesityl oxide, methoxypropanol, methyl isoamyl ketone, methyl isobutyl ketone, methyl laurate, methyl octanoate, methyl oleate, methylene chloride, mxylene, n-hexane, n-octylamine, octadecanoic acid, octylamine acetate, oleic acid, oleylamine, o-xylene, phénol, polyethylene glycol, propionic acid, propyl lactate, propylene carbonate, propylene glycol, propylene glycol methyl ether, p-xylene, toluene, triethyl phosphate, triethylene glycol, xylenesulfonic acid, paraffin, minerai oil, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, propylene glycol methyl ether, diethylene glycol methyl ether, methanol, éthanol, isopropanol, and alcohols of higher molecular weight, such as amyl alcohol, tetrahydrofurfuryl alcohol, hexanol, octanol, ethylene glycol, propylene glycol, glycerol, JV-mcthyl-2-pyrrolidone and the like.
Suitable solid carriers are, for example, talc, titanium dioxide, pyrophyllite clay, silica, attapulgite clay, kieselguhr, limestone, calcium carbonate, bentonite, calcium montmorillonite, cottonseed husks, wheat flour, soybean flour, pumice, wood flour, ground walnut shells, lignin and similar substances.
A large number of surface-active substances can advantageously be used in both solid and liquid formulations, especially in those formulations which can be diluted with a carrier prior to use. Surface-active substances may be anionic, cationic, non-ionic or polymeric and they can be used as emulsifiers, wetting agents or suspending agents or for other purposes. Typical surface-active substances include, for example, salts of alkyl sulfates, such as diethanolammonium lauryl Isulfate; salts of alkylarylsulfonates, such as calcium dodecylbenzenesulfonate; alkylphenol/alkylene oxide addition products, such as nonylphenol ethoxylate; alcohol/alkylene oxide addition products, such as tridecylalcohol ethoxylate; soaps, such as sodium stéarate; salts of alkylnaphthalenesulfonates, such as sodium j dibutylnaphthalenesulfonate; dialkyl esters of sulfosuccinate salts, such as sodium di(2ethylhexyl)sulfosuccinate; sorbitol esters, such as sorbitol oleate; quatemary amines, such as lauryltrimethylammonium chloride, polyethylene glycol esters of fatty acids, such as polyethylene glycol stéarate; block copolymers of ethylene oxide and propylene oxide; and salts of mono- and di-alkylphosphate esters; and also further substances described e.g. in
..........19869
McCutcheon's Détergents and Emulsifiers Annual, MC Publishing Corp., Ridgewood New
Jersey (1981). .
Further adjuvants that can be used in pesticidal formulations include crystallisation -----------inhibitors, viscosity modifiers, suspending agents, dyes, anti-oxidants, foaming agents, light ahsorbers, mixing auxiliaries, antifoams, complexing agents, neutralising or pH-modifying substances and buffers, corrosion inhibitors, fragrances, wetting agents, take-up enhancers, micronutrients, plasticisers, glidants, lubricants, dispersants, thickcners., antifrèezes, microbicides, and liquid and solid fertilisers.
. The formulations according to the invention can include an additive comprising ah oil 10 of vegetable or animal origin, a minerai oil, alkyl esters of such oils or mixtures of such oils and oil dérivatives. The amount of oil additive in the formulations according to the invention is generally from 0.01 to 10 %, based on the mixture to be applied. For example, the oil additive can be added to a spray tank in the desired concentration after a spray mixture has been prepared. Preferred oil additives comprise minerai oils or an oil of vegetable origin, for 15 example rapeseed oil, olive oil or sunflower oil, emulsified vegetable oil, alkyl esters of oils of vegetable origin, for example the methyl dérivatives, or an oil of animal origin, such as fish oil or beef tallow. Preferred oil additives comprise alkyl esters of C8-C22 fatty acids, especially the methyl dérivatives of C12-C18 fatty acids, for example the methyl esters of lauric acid, palmitic acid and oleic acid (methyl laurate, methyl palmitate and methyl oleate, 20 respectively). Many oil dérivatives are known from the Compendium of Herbicide
Adjuvants, 10ώ Edition, Southern Illinois University, 2010.
The inventive formulations generally comprise from 0.1 to 99 % by weight, especially from 0.1 to 95 % by weight, of polymorphs of the présent invention and from 1 to 99.9 % by weight of a formulation adjuvant which preferab|ly includes from 0 to 25 % by weight of a 25 surface-active substance. Whereas commercial products may preferably be formulated as concentrâtes, the end user will normally employ dilute formulations.
The rates of application vary within wide limits and dépend on the nature of the soil, the method of application, the crop plant, the pest to be controlled, the prevailing climatic conditions, and other factors govemed by the method of application, the time of application 7 30 and the target crop. As a general guideline the polymorphs of the invention may be applied at a rate of from 1 to 2000 1/ha, especially from 10 to 10001/ha.
Preferred formulations can hâve the following compositions (weight %):
Emulsifiable concentrâtes: active ingrédient: surface-active agent: liquid carrier:
Dusts:
active ingrédient: solid carrier:
Suspension concentrâtes: active ingrédient:
water:
surface-active agent:
Wettable powders: active ingrédient: surface-active agent:
solid carrier:
Granules: active ingrédient: solid carrier:
to 95 %, preferably 60 to 90 % to 30 %, preferably 5 to 20 % to 80 %, preferably 1 to 35 %
0.1 to 10 %, preferably 0.1 to 5 %
99.9 to 90 %, preferably 99.9 to 99 % to 75 %, preferably 10 to 50 % to 24 %, preferably 88 to 30 % to 40 %, preferably 2 to 30 %
0.5 to 90 %, preferably 1 to 80 %
0.5 to 20 %, preferably 1 to 15 % to 95 %, preferably 15 to 90 %
0.1 to 30 %, preferably 0.1 to 15 %
99.5 to 70 %, preferably 97 to 85 %
The following Examples further illustrate, but do not limit, the invention.
Wettable powders | a) | b) | c) |
active ingrédient | 25% | 50% | 75% |
sodium lignosulfonate | 5% | 5% | - |
sodium lauryl sulfate | 3% | - | 5% |
podium diisobutylnaphthalenesulfonate | - | 6% | 10% |
phénol polyethylene glycol ether | - | 2% | - |
(7-8 mol of ethylene oxide) | |||
highly dispersed silicic acid | 5% | 10% | 10% |
Kaolin | 1 62% | 27% | - |
The combination is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording wettable powders that can be diluted with water to give suspensions of the desired concentration.
Powders for dry seed treatment | a) | b) | c) |
active ingrédient | 25% | 50% | 75% |
light minerai oil | 5% | 5% | 5% |
highly dispersed silicic acid | 5% | 5% | - |
Kaolin | 65% | 40% | - |
Talcum | - | 20 |
The combination is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording powders that can be used directly for seed treatment.
Emulsifiable concentrate | |
active ingrédient | 10% |
octylphenol polyethylene glycol ether | 3% |
(4-5 mol of ethylene oxide) | |
calcium dodecylbenzenesulfonate | 3% |
castor oil polyglycol ether (35 mol of ethylene oxide) | 4% |
Cyclohexanone | 30% |
xylene mixture | 50% |
Emulsions of any required dilution, which can be used in plant protection, can be obtained 5 from this concentrate by dilution with water.
Dusts | a) | b) | c) |
active ingrédient | 5% | 6% | 4% |
Talcum | 95% | - | - |
Kaolin | - | 94% | - |
minerai Aller | - | - | 96% |
Ready-for-use dusts are obtained by mixing the combination with the carrier and grinding the mixture in a suitable mill. Such powders can also be used for dry dressings for seed.
Extruder granules | |
active ingrédient | 15% |
sodium lignosulfonate | 2% |
Carboxymethylcellulose | 1 % |
Kaolin | 82% |
The combination is mixed and ground with the adjuvants, and the mixture is moistened with water. The mixture is extruded and then dried in a stream of air.
Coated granules | |
active ingrédient | 8% |
polyethylene glycol (mol. wt. 200) | 3% |
Kaolin ! | 89% |
The finelÿ ground combination is uniformly applied, in a mixer, tô the kaolin moistened with polyethylene glycol. Non-dusty coated granules are obtained in this manner.
Suspension concentrate
active ingrédient | 40 % |
propylene glycol | 10% |
nonylphenol polyethylene glycol ether (15 mol of ethylene oxide) | 6% |
Sodium lignosulfonate | 10% |
Carboxymethylcellulose | 1 % |
silicone oil (in the form of a 75 % émulsion in water) | 1 % |
Water | 32% |
The finely ground combination is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water. Using such dilutions, living plants as well as plant propagation material can be treated and protected against infestation by microorganisms, by spraying, pouring or immersion.
Howable concentrate for seed treatment | |
active ingrédient | 40% |
propyleneglycol | 5% |
copolymer hutanol PO/EO | 2% |
Tristyrenephenole with 10-20 moles EO | 2% |
l,2-benzisothiazolin-3-one (in the form of a 20% solution in water) | 0.5 % |
monoazo-pigment calcium sait | 5% |
Silicone oil (in the form of a 75 % émulsion in water) | 0.2 % |
Water | 45.3 % |
The finely ground combination is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water. Using such dilutions, living plants as well as plant propagation material can be treated 10 and protected against infestation by microorganisms, by spraying, pouring or immersion.
Slow Release Capsule Suspension parts of the active ingrédient are mixed with 2 parts of an aromatic solvent and 7 parts of toluene diisocyanate/polymethylene-polyphenylisocyanate-mixture (8:1). This mixture is emulsified in a mixture of 1.2 parts of polyvinylalcohol, 0.05 parts of a defoamer and 51.6 parts of water until the desired particle size is achieved. To this émulsion a mixture of 2.8 parts 1,6-diapiinohexane in 5.3 parts of water is added. The mixture js agitated until the polymerization reaction is completed. The obtained capsule suspension is stabilized by adding 0.25 parts of a thickener and 3 parts of a dispersing agent. The capsule suspension formulation contains 28% of the active ingrédient. The medium capsule diameter is 8-15 microns. The resulting formulation is applied to seeds as an aqueous suspension in an apparatus suitable for that purpose.
Each of the above formulations can be prepared as a package containing the polymorph or polymorphs of the invention together with other ingrédients of the formulation (diluents, emulsifiers, surfactants, etc.). The formulations can also be prepared by a tank mix method, in which the ingrédients are obtained separately and combined at the grower site.
These formulations can be applied to the areas where control is desired by conventional methods. Dust and liquid formulations, for example, can be applied by the use of power-dusters, broom and hand sprayers and spray dusters. The formulations can also be applied from airplanes as a dust or a spray or by rope wick applications. Both solid and liquid formulations may also be applied to the soil in the locus of the plant to be treated . allowing the active ingrédient to penetrate the plant through the roots.
The polymorphs of the invention and compositions thereof are also be suitable for the protection of plant propagation material, for example seeds, such as fruit, tubers or kernels, or nursery plants, against pests of the abovementioned type. The propagation material can be treated with the polymorph prior to planting, for example seed can be treated prior to sowing. Alternatively, the polymorph can be applied to seed kernels (coating), either by soaking the kernels in a liquid composition or by applying a layer of a solid composition. It is also possible to apply the compositions when the propagation material is planted to the site of application, for example into the seed furrow during drilling. These treatment methods for plant propagation material and the plant propagation material thus treated are further subjects of the invention. Typical treatment rates would dépend on the plant and pest/fungi to be controlled and are generally between 1 to 200 grams per 100 kg of seeds, preferably between 5 to 150 grams per 100 kg of seeds, such as between 10 to 100 grams per 100 kg of seeds.
The term seed embraces seeds and plant propagules of ail kinds including but not limited to true seeds, seed pièces, suckers, coms, bulbs, fruit, tubers, grains, rhizomes, cuttings, eut shoots and the like and means in a preferred embodiment true seeds.
The present invention lalso comprises seeds coated or treated with or containin|g a polymorph of the invention. The term coated or treated with and/or containing generally signifies that the active ingrédient is for the most part on the surface of the seed at the time of application, although a greater or lesser part of the ingrédient may penetrate into the^ seed material, depending on the method of application. When the said seed product is (re)planted, it may absorb the active ingrédient. In an embodiment, the present invention makes available a plant propagation material adhered thereto with a compound of formula (I). Further, it is hereby made available, a composition comprising a plant propagation material treated with a compound of formula (I).
Seed treatment comprises ail suitable seed treatment techniques known in the art, such as seed dressing, seed coatmg, seed dustrng, seed soakmg and seed pelletmg. The seed treatment application of the compound formula (I) can be carried out by any known methods, such as spraying or by dusting the seeds before sowing or during the sowing/planting of the seeds.
Suitably, the agrochemical compositions and formulations of the présent invention are applied prior to disease development. Rates and frequency of use of the formulations are those conventionally used in the art and will dépend on the risk of infestation by the insect pathogen.
The activity of compositions comprising compounds and polymorphs according to the invention can be broadened considerably, and adapted to prevailing circumstances, by including other active substances. The active substances can be of Chemical or biological in type, and in the case of biological could be further modified from the biological species derived in nature. Active substances include substances that control, repel or attract pests that damage or harm useful plants in general, but also substances that improve the growth of a useful plant, such as plant growth regulators, and substances that improve the performance of the active substance, such as synergists. Examples are insecticides, acaricides, nematicides, molluscicides, aligicides, virusicides, rodenticide, bactéricides, fungicides, chemosterilants, anthelmintics. Examples of a biological active substance include baculovirus, plant extract, and bacteria.
Accordingly, the présent invention provides for the use of a composition according to the présent invention together with one or more pesticides, plant nutrients or plant fertilizers. The combination may also encompass spécifie plant traits incorporated into the plant using any means, for example conventiona| breeding or genetic modification. |
The mixtures of the polymorphs of the invention with other active substances may also hâve further surprising advantages which can also be described, in a wider sense, as । synergistic activity. For example, beljter tolérance by plants, reduced phytotoxicity, insects | can be controlled in their different development stages, or better behaviour relating to production, for example grinding or mixing, storage or use.
Individual active substances can occur in more than one group or class, and at more than one place within a group or class: information about the active substances, their spectrum, sources and classifications can be found from Compendium of Pesticide Common
Names (see http://www.alanwood.net/pesticides/index.html) or from the Pesticide Manual created by the British Crop Production Counci (see http://bcpcdata.com/pesticide- manual.html).
Preferred mixtures are indicated below where the polymorph or polymorphs of of the 5 invention are indicated as “I”:
Compositions comprising an adjuvant include I + compounds selected from the group of substances consisting of petroleum oils.
Compositions comprising an acaricide include I + l,l-bis(4-chlorophenyl)-2ethoxyethanol, I + 2,4-dichlorophenyl benzenesulfonate, I + 2-fluoro-7V-methyΙ-ΛΜ- naphthylacetamide, I + 4-chlorophenyl phenyl sulfone, I + abamectin, I + acequinocyl, I + acetoprole, I + acrinathrin, I + aldicarb, I + aldoxycarb, I + alpha-cypermethrin, I + amidithion, I + amidoflumet, I + amidothioate, I + amiton, I + amiton hydrogen oxalate, I + amitraz, I + aramite, I + arsenous oxide, I + AVI 382,1 + AZ 60541,1 + azinphos-ethyl, I + azinphos-methyl, I + azobenzene, I + azocyclotin, I + azothoate, I + benomyl, I + benoxafos,
I + benzoximate, I + benzyl benzoate, I + bifenazate, I + bifenthrin, I + binapacryl, I + brofenvalerate, I + bromocyclen, I + bromophos, I + bromophos-ethyl, I + bromopropylate, I + buprofezin, I + butocarboxim, I + butoxycarboxim, I + butylpyridaben, I + calcium polysulfide, I + camphechlor, I + carbanolate, I + carbaryl, I + carbofuran, I + carbophenothion, I + CGA 50’439,1 + chinomethionat, I + chlorbenside, I + chlordimeform, 20 I + chlordimeform hydrochloride, I + chlorfenapyr, I + chlorfenethol, I + chlorfenson, I + chlorfensulfide, I + chlorfenvinphos, 14- chlorobenzilate, I + chloromebuform, I + chloromethiuron, I + chloropropylate, I + chlorpyrifos, I + chlorpyrifos-methyl, I + chlorthiophos, I + cinerin I, I + cinerin II, I + cinerins, I + clofentezine, I + closantel, I + coumaphos, I + crotamiton, I + crotoxyphos, + cufraneb, I + cyanthoate, I + cyflumetofen, I + cyhalothrin, I + cyhexatin, I + cypermethrin, I + DCPM, I + DDT, I + demephion, I + demephion-O, I + demephion-S, I + demeton, I + demeton-methyl, I + demeton-O, I + demeton-O-methyl, I + demeton-S, I + demeton-S-methyl, I + demeton-S-methylsulfon, I + diafenthiuron, I + dialifos, I + diazinon, I + dichlofluanid, I + dichlorvos, I + dicliphos, I + dicofol, I + dicrotophos, I + dienochlor, I + dimefox, I + dimethoate, I + dinactin, I + dinex,
I + dinex-diclexine, I + dinobuton, I + dinocap, I + dinocap-4,1 + dinocap-6,1 + dinocton, I + dinopenton, I + dinosulfon, I + dinoterbon, I + dioxathion, I + diphenyl sulfone, I + disulfiram, I + disulfoton, I + DNOC, I + dofenapyn, I + doramectin, I + endosulfan, I + endothion, I + EPN, I + eprinomectin, I + ethion, I + ethoate-methyl, I + etoxazole, I + etrimfos, I + fenazaflor, I + fenazaquin, I + fenbutatin oxide, I + fenothiocarb, I + fenpropathrin, I + fenpyrad, I + fenpyroximate, I + fenson, I + fentrifanil, I + fenvalerate, I + fipronil, I + fluacrypyrim, I + fluazuron, I + flubenzimine, I + flucycloxuron, I + flucythrinate, I + fluenetil, I + flufenoxuron, I + flumethrin, I + fluorbenside, I + fluvalinate, I + FMC 1137,1 + formetanate, I + formetanate hydrochloride, I + formothion, I + formparanate, I + gamma-HCH, I + glyodin, I + halfenprox, I + heptenophos, I + hexadecyl cyclopropanecarboxylate, I + hexythiazox, I + iodomethane, I + isocarbophos, I + isopropyl O-(methoxyaminothiophosphoryl)salicylate, I + ivermectin, I +jasmolin I, I + jasmolin Π, I +jodfenphos, I + lindane, I + lufenuron, I + malathion, I + malonoben, I + mecarbam, I + mephosfolan, I + mesulfen, I + methacrifos, I + methamidophos, I + methidathion, I + methiocarb, I + methomyl, I + methyl bromide, I + metolcarb, I + mevinphos, I + mexacarbate, I + milbemectin, I + milbemycin oxime, I + mipafox, I + monocrotophos, I + morphothion, I + moxidectin, I + naled, I + NC-184,1 + NC-512,1 + nifluridide, I + nikkomycins, I + nitrilacarb, I + nitrilacarb 1:1 zinc chloride complex, I + NNI-0101,1 + NNI-0250,1 + omethoate, I + oxamyl, I + oxydeprofos, I + oxydisulfoton, I + pp'-DDT, I + parathion, I + permethrin, I + petroleum oils, I + phenkapton, I + phenthoate, I + phorate, I + phosalone, I + phosfolan, I + phosmet, I + phosphamidon, I + phoxim, I + pirimiphosmethyl, I + polychloroterpenes, I + polynactins, I + proclonol, I + profenofos, I + promacyl, I + propargite, I + propetamphos, I + propoxur, I + prothidathion, I + prothoate, I + pyrethrin I, I + pyrethrin Π, I + pyrethrins, I + pyridaben, I + pyridaphenthion, I + pyrimidifen, I + pyrimitate, I + quinalphos, I + quintiofos, I + R-1492,1 + RA-17,1 + rotenone, I + schradan, I + sebufos, I + selamectin, I + SI-0009,1 + sophamide, I + spirodiclofen, I + spiromesifen, I + SSI-121,1 + sulfiram, I + sulfluramid, I + sulfotep, I + sulfur, I + SZI-121,1 + taufluvalinate, I + tebufenpyrad, I + ΊΈΡΡ, I + terbam, I + tetrachlorvinphos, I + tetradifon, I + tetranactin, I + tetrasul, I + thiafenox, I + thiocarboxime, I + thiofanox, I + thiometon, I + thioquinox, I + thuringiensin, I + triamiphos, I + triaratkene, I + triazophos, I + triazuron, I + trichlorfon, I + trifenofos, I + trinactin, I + vamidothion, I + vaniliprole and I + YI-5302.
Compositions comprising an anthelmintic include I + abamectin, I + crufomate, I + doramectin, I + emamectin, I + emamectin benzoate, I + eprinomectin, I + ivermectin, I + milbemycin oxime, I + moxidectin, I + piperazine, I + selamectin, I + spinosad and I + thiophanate.
Compositions comprising an avicide include I + chloralose, I + endrin, I + fenthion, I + pyridin-4-amine and I + strychnine.
Compositions comprising a biological control agent include I + Adoxophyes orana GV,
I + Agrobacterium radiobacter, I + Amblyseius spp., I + Anagrapha falcifera NPV, I + Anagrus atomus, I + Aphelinus abdominalis, I+Aphidius colemani, I + Aphidoletes aphidimyza, I + Autographa califomica NPV, I + Bacillusfirmus, I + Bacillus sphaericus Neide, I + Bacillus thuringiensis Berliner, I + Bacillus thuringiensis subsp. aizawai, I + Bacillus thuringiensis subsp. israelensis, I + Bacillus thuringiensis sdbsp.japonensis, I + Bacillus thuringiensis subsp. kurstaki, I + Bacillus thuringiensis subsp. tenebrionis, I + Beauveria bassiana, I + Beauveria brongniartii, I + Chrysoperla camea, 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 + Hippodamia convergens, I + Leptomastix dactylopii, I + Macrolophus caliginosus, I + Mamestra brassicae NPV, I + Metaphycus helvolus, I + Metarhizium anisopliae var. acridum, I + Metarhizium anisopliae var. anisopliae, I + Neodiprion sertifer NPV and N. lecontei NPV, I + Orius spp., I + Paecilomyces fumosoroseus, I + Phytoseiulus persimilis, I + Spodoptera exigua multicapsid nuclear polyhedrosis virus, I + Steinemema bibionis, I + Steinernema carpocapsae, I + Steinemema feltiae, I + Steinemema glaseri, I + Steinemema riobrave, I + Steinemema riobravis, I + Steinemema scapterisci, I + Steinemema spp., I + Trichogramma spp., I + Typhlodromus occidentalis and I + Verticillium lecanii.
Compositions comprising a soil sterilant include I + iodomethane and methyl bromide.
Compositions comprising a chemosterilant include I + apholate, I + bisazir, I + busulfan, I + diflubenzuron, I + dimatif, I + hemel, I + hempa, I + metepa, I + methiotepa, I + methyl apholate, I + morzid, I + penfluron, I + tepa, I + thiohempa, I + thiotepa, I + tretamine and I + uredepa.
I I
Compositions comprising an insect pheromone include I + (£)-dec-5-en-l-yl acetate with (E)-dec-5-en-l-ol, I + (E)-tridec-4-en-l-yl acetate, I + (£)-6-methylhept-2-en-4-ol, I + (E.ZJ-tetradeca-^lO-dien-l-yl acetate, I + (Z)-dodec-7-en-l-yl acetate, I + (Z)-hexadec-l 1! I enal, 14- (Z)-hexadec-l 1-en-l-yl acetate, I + (Z)-hexadec-13-en-l 1-yn-l-yl acetate, I + (Z)icos-13-en-10-one, I + (Z)-tetradec-7-en-l-al, I + (Z)-tetradec-9-en-l-ol, I + (Z)-tetradec-9en-l-yl acetate, I + (7Æ',9Z)-dodeca-7,9-dien-l-yl acetate, I + (9Z,1 l£)-tetradeca-9,l 1-dien-lyl acetate, I + (9Z, 12£)-tetradeca-9,12-dien-l-yl acetate, I + 14-methyloctadec-l-ene, 1 + 4methylnonan-5-ol with 4-methylnonan-5-one, I + alpha-multistriatin, I + brevicomin, I + codlelure, I + codlemone, I + cuelure, I + disparlure, I + dodec-8-en-l-yl acetate, I + dodec
9-en-l-yl acetate, I + dodeca-8,1 + 10-dien-l-yl acetate, I + dominicalure, I + ethyl 4methyloctanoate, I + eugenol, I + frontalin, I + gossyplure, I + grandlure, I + grandlure I, I + grandlure Π, I + grandlure ΙΠ, I + grandlure IV, I + hexalure, I + ipsdienol, I + ipsenol, I + japonilure, I + lineatin, I + litlure, I + looplure, I + medlure, I + megatomoic acid, I + methyl eugenol, I + muscalure, I + octadeca-2,13-dien-l-yl acetate, I + octadeca-3,13-dien-l-yl acetate, I + orfralure, I + oryctalure, I + ostramone, I + siglure, I + sordidin, I + sulcatol, I + tetradec-11-en-l-yl acetate, I + trimedlure, I + trimedlure A, I + trimedlure Bj, I + trimedlure B2,1 + trimedlure C and I + trunc-call.
Compositions comprising an insect repellent include I + 2-(octylthio)ethanol, I + butopyronoxyl, I + butoxy(polypropylene glycol), I + dibutyl adipate, I + dibutyl phthalate, I + dibutyl succinate, I + diethyltoluamide, I + dimethyl carbate, I + dimethyl phthalate, I + ethyl hexanediol, I + hexamide, I + methoquin-butyl, I + methylneodecanamide, I + oxamate and I + picaridin.
Compositions comprising an insecticide include I + 1-dichloro-l-nitroethane, I + 1,1dichloro-2,2-bis(4-ethylphenyl)ethane ,1+,1+ 1,2-dichloropropane, I + 1,2-dichloropropane with 1,3-dichloropropene, I + l-bromo-2-chloroethane, I + 2,2,2-trichloro-l-(3,4-dichlorophenyl)ethyl acetate, I + 2,2-dichlorovinyl 2-ethylsulfmylethyl methyl phosphate, I + 2-(1,3dithiolan-2-yl)phenyl dimethylcarbamate, I + 2-(2-butoxyethoxy)ethyl thiocyanate, 1 + 2(4,5-dimethyl-l,3-dioxolan-2-yl)phenyl methylcarbamate, I + 2-(4-chloro-3,5xylyloxy)ethanol, I + 2-chlorovinyl diethyl phosphate, I + 2-imidazolidone, 1 + 2isovalerylindan-l,3-dione, I + 2-methyl(prop-2-ynyl)aminophenyl methylcarbamate, 1 + 2thiocyanatoethyl laurate, I + 3-bromo-l-chloroprop-l-ene, I + 3 -methyl- 1-pheny lpyrazol-5yl dimethylcarbamate, I + 4-methyl(prop-2-ynyl)amino-3,5-xylyl methylcarbamate, I + 5,5dimethyl-3-oxocyclohex-l-enyl dimethylcarbamate, I + abamectin, I + acephate, I + acetamiprid, I + Lcethion, I + acetoprole, I + acrinathrin, I + acrylonitrilel, I + alanycarb, I + aldicarb, I + aldoxycarb, I + aldrin, I + allethrin, I + allosamidin, I + allyxycarb, I + alphacypermethrin, I + alpha-ecdysone, I + aluminium phosphide, I + amidithion, I + amidothioate, I + aminocarb, I + amiton, I + amiton hydrogen oxalate, I jt- amitraz, I + anabasine, I + athidathion, I + AVI 382,1 + AZ 60541,1 + azadirachtin, I + azamethiphos, I + azinphos-ethyl, I + azinphos-methyl, I + azothoate, I + Bacillus thuringiensis delta endotoxins, I + barium hexafluorosilicate, I + barium polysulfïde, I + barthrin, I + Bayer 22/190,1 + Bayer 22408,1 + bendiocarb, I + benfuracarb, I + bensultap, I + beta-cyfluthrin, I + beta-cypermethrin, I + bifenthrin, I + bioallethrin, I + bioallethrin 5-cyclopentenyl isomer,
I + bioethanomethrin, I + biopermethrin, I + bioresmethrin, I + bis(2-chloroethyl) ether, I + bistrifluron, I + borax, I + brofenvalerate, I + bromfenvinfos, I + bromocyclen, I + hromoDDT, I + bromophos, I + bromophos-ethyl, I + bufencarb, I + buprofezin, I + butacarb, I + butathiofos, I + butocarboxim, I + butonate, I + butoxycarboxim, I + butylpyridaben, I + cadusafos, I + calcium arsenate, I + calcium cyanide, I + calcium polysulfide, I + camphechlor, I + carbanolate, I + carbaryl, I + carbofuran, I + carbon disulfide, I + carbon tetrachloride, I + carbophenothion, I + carbosulfan, I + cartap, I + cartap hydrochloride, I + cevadine, I + chlorbicyclen, I + chlordane, I + chlordecone, I + chlordimeform, I + chlordimeform hydrochloride, I + chlorethoxyfos, I + chlorfenapyr, I + chlorfenvinphos, I + chlorfluazuron, I + chlormephos, I + chloroform, I + chloropicrin, I + chlorphoxim, I + chlorprazophos, I + chlorpyrifos, I + chlorpyrifos-methyl, I + chlorthiophos, I + chromafenozide, I + cinerin I, I + cinerin II, I + cinerins, I + cis-resmethrin, I + cismethrin, I + clocythrin, I + cloethocarb, I + closantel, I + clothianidin, I + copper acetoarsenite, I + copper arsenate, I + copper oleate, I + coumaphos, I + coumithoate, I + crotamiton, I + crotoxyphos, I + crufomate, I + cryolite, I + CS 708,1 + cyanofenphos, I + cyanophos, I + cyanthoate, I + cyclethrin, ! + cycloprothrin, I + cyfluthrin, I + cyhalothrin, I + cypermethrin, I + cyphenothrin, I + cyromazine, I + cythioate, I + tMimonene, I + d-tetramethrin, I + DAEP, I + dazomet, I + DDT, I + decarbofuran, I + deltamethrin, I + demephion, I + demephion-O, I + demephion-S, I + demeton, I + demeton-methyl, I + demeton-O, I + demeton-O-methyl, I + demeton-S, I + demeton-S-methyl, I + demeton-S-methylsulphon, I + diafenthiuron, I + dialifos, I + diamidafos, I + diazinon, I + dicapthon, I + dichlofenthion, I + dichlorvos, I + dicliphos, I + dicresyl, I + dicrotophos, I + dicyclanil, I + dieldrin, I + diethyl 5-methylpyrazol-3-yl phosphate, I + diflubenzuron, I + dilor, I + dimefluthrin, I + dimefox, I + dimetan, I + dimethoate, I + dimethrin, I + dimethylvinphos, I + dimetilan, I + dinex, I + dinex-diclexine, I + dinoprop, I + dinosam, I + dinoseb, I + dinotefuran, I + diofenolan, I + dioxahenzofos, I + dioxaiiarb, I + dioxathion, I + disulfoton, I + dithicrofos, I + D^NOC, I + doramectin, I + DSP, I + ecdysterone, I + El 1642,1 + emamectin, I + emamectin benzoate, I + EMPC, I + empenthrin, I + endosulfan, I + endothion, I + endrin, I + EPBP, I + EPN, I + epofenonane, I + eprinomectin, I + esfenvalerate, I + etaphos, I + ethiofencarb, I -- ethion, I + ethiprole, I + ethoate-methyl, I + ethoprophos, I + ethyl formate, I + ethyl-DDD, I + ethylene dibromide, I + ethylene dichloride, I + ethylene oxide, I + etofenprox, I + etrimfos, I + EXD, I + famphur, I + fenamiphos, I + fenazaflor, I + fenchlorphos, I + fenethacarb, I + fenfluthrin, I + fenitrothion, I + fenobucarb, I + fenoxacrim, I + fenoxycarb, I + fenpirithrin, I + fenpropathrin, I + fenpyrad, I + fensulfothion, I + fenthion, I + fenthion-ethyl, I + fenvalerate, I + fipronil, I + flonicamid, I + flubendiamide, I + flucofuron, I + flucycloxuron,
I + flucythrinate, I + fluenetil, I + flufenerim, I + flufenoxuron, I + flufenprox, I + flumethrin, I + fluvalinate, I + FMC 1137,1 + fonofos, I + formetanate, I + formetanate hydrochloride, I + formothion, I + formparanate, I + fosmethilan, I + fospirate, I + fosthiazate, I + fosthietan, I + furathiocarb, I + furethrin, I + gamma-cyhalothrin, I + gammaHCH, I + guazatine, I + guazatine acétates, I + GY-81,1 + halfenprox, I + halofenozide, I + HCH, I + HEOD, I + heptachlor, I + heptenophos, I + heterophos, I + hexaflumuron, I + HHDN, I + hydramethylnon, I + hydrogen cyanide, I + hydroprene, I + hyquincarb, I + imidacloprid, I + imiprothrin, I + indoxacarb, I + iodomethane, I + IP SP, I + isazofos, I + isohenzan, I + isocarbophos, I + isodrin, I + isofenphos, I + isolane, I + isoprocarb, I + isopropyl O-(methoxyaminothiophosphoryl)salicylate, I + isoprothiolane, I + isothioate, I + isoxathion, I + ivermectin, I +jasmolin I, I +jasmolin Π, I + jodfenphos, I + juvénile hormone I, I + juvénile hormone Π, I + juvénile hormone ΙΠ, I + kelevan, I + kinoprene, I + lambda-cyhalothrin, I + lead arsenate, I + lepimectin, I + leptophos, I + lindane, I + lirimfos, I + lufenuron, I + lythidathion, I + m-cumenyl methylcarbamate, I + magnésium phosphide, I + malathion, I + malonoben, I + mazidox, I + mecarbam, I + mecarphon, I + menazon, I + mephosfolan, I + mercurous chloride, I + mesulfenfos, I + metafhimizone, I + metam, I + metam-potassium, I + metam-sodium, I + methacrifos, I + methamidophos, I + methanesulfonyl fluoride, I + methidathion, I + methiocarb, I + methocrotophos, I + methomyl, I + methoprene, I + methoquin-butyl, I + methothrin, I + methoxychlor, I + methoxyfenozide, I + methyl bromide, I + methyl isothiocyanate, I + methylchloroform, I + methylene chloride, I + metofluthrin, I + metolcarb, I + metoxadiazone, I + mevinphos, I + mexacarbate, I + milbemectin, I + milbemycin oxime, I + mipafox, I + mirex, I + monocrotophos, I + morphothion, I + moxidectin, I + naftalofos, I + naled, I + naphthalene, I + NC-170,1 + NC-184,1 + nicotine, I + nicotine sulfate, I + nifluridide, I + nitenpyram, I + nithiazine, I + nitrilacarb, I + nitrillacarb 1:1 zinc chloride complex, I + NNI-0101,1 + NnJ0250,1 + nomicotine, I + novaluron, I + noviflumuron, I + O-5-dichloro-4-iodophenyl Oethyl ethylphosphonothioate, I + Ο,Ο-diethyl O-4-methyl-2-oxo-2H-chromen-7-yl । phosphorothioate, I + Ο,Ο-diethyl O-6-methyl-2-propyIpyrimidin-4-yl phosphorothioate, I + O.O, O', O'-tetrapropyl dithiopyrophosphate, I + oleic acid, I + omethoate, I + oxamyl, I + oxydemeton-methyl, I + oxydeprofos, I + oxydisulfoton, I + pp'-DDT, I + paradichlorobenzene, I + parathion, I + parathion-methyl, I + penfluron, I + pentachlorophenol, I + pentachlorophenyl laurate, I + permethrin, I + petroleum oils, I + PH 60-38,1 + phenkapton, I + phenothrin, I + phenthoate, I + phorate+ TX, I + phosalone, I + phosfolan, I + phosmet, I + phosnichlor, I + phosphamidon, I + phosphine, I + phoxim, I + phoximmethyl, I + pinmetaphos, I + pirimicarb, I + pirimiphos-ethyl, I + pirimiphos-methyl, I + polychlorodicyclopentadiene isomers, I + polychloroterpenes, I + potassium arsenite, I + potassium thiocyanate, I + prallethrin, I + precocene I, I + precocene Π, I + precocene III, I + primidophos, I + profenofos, I + profluthrin, I + promacyl, I + promecarb, I + propaphos, I + propetamphos, I + propoxur, I + prothidathion, I + prothiofos, I + prothoate, I + protrifenbute, I + pymetrozine, I + pyraclofos, I + pyrazophos, I + pyresmethrin, I + pyrethrin I, I + pyrethrin Π, I + pyrethrins, I + pyridaben, I + pyridalyl, I + pyridaphenthion, I + pyrimidifen, I + pyrimitate, I + pyriproxyfen, I + quassia, I + quinalphos, I + quinalphosmethyl, I + quinothion, I + quintiofos, I + R-1492,1 + rafoxanide, I + resmethrin, I + rotenone, I + RU 15525,1 + RU 25475,1 + ryania, I + ryanodine, I + sabadilla, I + schradan, I + sebufos, I + selamectin, I + SI-0009,1 + SI-0205,1 + SI-0404,1 + SI-0405,1 + silafluofen, I + SN 72129,1 + sodium arsenite, I + sodium cyanide, I + sodium fluoride, I + sodium hexafluorosilicate, I + sodium pentachlorophenoxide, I + sodium selenate, I + sodium thiocyanate, I + sophamide, I + spinosad, I + spiromesifen, I + spirotetrmat, I + sulcofuron, I + sulcofuron-sodium, I + sulfluramid, I + sulfotep, I + sulfuryl fluoride, I + sulprofos, I + tar oils, I + tau-fluvalinate, I + tazimcarb, I + TDE, I + tebufenozide, I + tebufenpyrad, I + tebupirimfos, I + teflubenzuron, I + tefluthrin, I + temephos, I + TEPP, I + terallethrin, I + terbam, I + terbufos, I + tetrachloroethane, I + tetrachlorvinphos, I + tetramethrin, I + theta-cypermethrin, I + thiacloprid, I + thiafenox, I + thiamethoxam, I + thicrofos, I + thiocarboxime, I + thiocyclam, I + thiocyclam hydrogen oxalate, I + thiodicarb, I + thiofanox, I + thiometon, I + thionazin, I + thiosultap, I + thiosultap-sodium, I + thuringiensin, I + tolfenpyrad, I + tralomethrin, I + transfluthrin, I + transpermethrin, I + triamiphos, I + triazamate, I + triazophos, I + triazuron, I + trichlorfon, I + trichlormetaphos3,1 + trichloronat, I + trifenofos, I + triflumuron, I + trimethacarb, I + triprene, I + vamidothion, I + vaniliprole, I + veratridinJ, I + veratrine, I + XMC, I + xylylcarb, I + YI5302,1 + zeta-cypermethrin, I + zetamethrin, I + zinc phosphide, I + zolaprofos and ZXI 8901,1 + cyantraniliprole, I + chlorantraniliprole, I + cyenopyrafen, I + cyflumetofen, I + pyrifluquinazon, I + spinetoram, I + spirotetramat, I + sulfoxaflor, I + flufiprole, I + meperfluthrin, I + tetramethylfluthrin, I + triflumezopyrim.
Compositions comprising a molluscicide include I + bis(tributyltin) oxide, I + bromoacetamide, I + calcium arsenate, I + cloethocarb, I + copper acetoarsenite, I + copper sulfate, I + fentin, I + ferrie phosphate, I + metaldehyde, I + methiocarb, I + niclosamide, I + niclosamide-olamine, I + pentachlorophenol, I + sodium pentachlorophenoxide, I + tazimcarb, I + thiodicarb, I + tributyltin oxide, I + trifenmorph, I + trimethacarb, I + tnphenyltm acetate and triphenyltin hydroxide, I + pyriprole.
Compositions comprising a nematicide include 1+ AKD-3088,1 + l,2-dibromo-3chloropropane, I + 1,2-dichloropropane, I + 1,2-dichloropropane with 1,3-dichloropropene, I + 1,3-dichloropropene, I + 3,4-dichlorotetrahydrothiophene 1,1-dioxide, I + 3-(4chlorophenyl)-5-methylrhodanine, 1 + 5-methyl-6-thioxo-l,3,5-thiadiazinan-3-ylacetic acid, I + 6-isopentenylaminopurine, I + abamectin, I + acetoprole, I + alanycarb, I + aldicarb, I + aldoxycarb, I + AZ 60541,1 + benclothiaz, I + benomyl, I + butylpyridaben, I + cadusafos, I + carbofuran, I + carbon disulfide, I + carbosulfan, I + chloropicrin, I + chlorpyrifos, I + cloethocarb, I + cytokinins, I + dazomet, I + DBCP, I + DCIP, I + diamidafos, I + dichlofenthion, I + dicliphos, I + dimethoate, I + doramectin, I + emamectin, I + emamectin benzoate, I + eprinomectin, I + ethoprophos, I + ethylene dibromide, I + fenamiphos, I + fenpyrad, I + fensulfothion, I + fosthiazate, I + fosthietan, I + furfural, I + GY-81,1 + heterophos, I + iodomethane, I + isamidofos, I + isazofos, I + ivermectin, I + kinetin, I + mecarphon, I + metam, I + metam-potassium, I + metam-sodium, I + methyl bromide, I + methyl isothiocyanate, I + milbemycin oxime, I + moxidectin, I + Myrothecium verrucaria composition, I + NC-184,1 + oxamyl, I + phorate, I + phosphamidon, I + phosphocarb, I + sebufos, I + selamectin, I + spinosad, I + terbarn, I + terbufos, I + tetrachlorothiophene, I + thiafenox, I + thionazin, I + triazophos, I + triazuron, I + xylenols, I + YI-5302 and zeatin, I + fluensulfone.
Compositions comprising a synergist include I + 2-(2-butoxyethoxy)ethyl piperonylate, I + 5-(l,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone, I + famesol with nerolidol, I + MB599,1 + MGK 264,1 + piperonyl butoxide, I + piprotal, I + propyl isomer, I + S421,1 + sesamex, I + sesasmolin and I + sulfoxide.
Compositions comprising an animal repellent include 1+ anthraquinone, I + chloralose, I + copper naphthenate, I + copper oxychloride, I + diazinon, I + dicyclopentadiene, I + guazatine, I + guazatine acétates, I + methiocarb, 14 pyridin-4-amine, I + thiram, I + trimethacarb, I + zinc naphthenate and I + ziram. I
Further 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 + Helicoverpa armigera 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 420,1 + QRD 452,1 + QRD 460,1 + Terpenoid blends, I + Terpenoids, I + Tetraniliprole, and I + a-terpinene.
Composition also include mixtures of the polymorph or polymorphs of the invention and an active substance referenced by a code, such as I + code AE 1887196 (BSCBX60309), I + code NNI-0745 GR, I + code IKI-3106,1 + code JT-L001,1 + code ZNQ08056,1 + code IPPA152201,1 + code HNPC-A9908 (CAS: [660411-21-2]), I + code HNPC-A2005 (CAS: [860028-12-2]), I + code JS118,1 + code ZJ0967,1 + code ZJ2242,1 + code JS7119 (CAS: [929545-74-4]), I + code SN-1172,1 + code HNPC-A9835,1 + code HNPC-A9955,1 + code HNPC-A3061,1 + code Chuanhua 89-1,1 + code IPP-10,1 + code ZJ3265,1 + code JS9117,1 + code SYP-9080,1 + code ZJ3757,1 + code ZJ4042,1 + code ZJ4014,1 + code ΓΓΜ-121,1 + code DPX-RAB55 (DKI-2301), I + code Me5382,1 + code NC-515,1 + code NA-89,1 + code MIE-1209,1 + code MCI-8007,1 + code BCS-CL73507,1 + code S-1871,1 + code DPX-RDS63, and I + code AKD-1193.
Whilst compositions comprising the polymorph or polymorphs of the invention and another insecticide etc. are explicitly disclosed above, the skilled man will appreciate that the invention extends to three-way, and further multiple combinations comprising the above two-way mixtures.
The weight ratio of the polymorph or polymorphs of the invention and 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.
The polymorphs of the invention are also useful in the field of animal health, e.g. they may be used against parasitic invertebrate pests, more preferably against parasitic invertebrate pests in or on an animal. Examples of pests include nematodes, trematodes, cestodes, flies, mites, tricks, lice, fleas, true bugs and maggots. The animal may be a nonhuman animal, e.g. an animal associated with agriculture, e.g. a cow, a pig, a sheep, a goat, a horse, or a donkey, or a companion animal, e.g. a dog or a cat.
In a further aspect the invention provides a polymorph of the invention for use in a method of therapeutic treatment.
In a further aspect the invention relates to a method of controlling parasitic invertehrate pests in or on an animal comprising administering a pesticidally effective amount of a polymorph of the invention. The administration may be for example oral administration, parentéral administration or external administration, e.g. to the surface of the animal body. In a further aspect the invention relates to a polymorph of the invention for controlling parasitic invertehrate pests in or on an animal. In a further aspect the invention relates to use of a polymorph of the invention in the manufacture of a médicament for controlling parasitic invertehrate pests in or on an animal.
In a further aspect, the invention relates to a method of controlling parasitic invertehrate pests comprising administering a pesticidally effective amount of a polymorph of the invention to the environment in which an animal résides.
In a further aspect the invention relates to a method of protecting an animal from a parasitic invertehrate pest comprising administering to the animal a pesticidally effective amount of a polymorph of the invention. In a further aspect the invention relates to a polymorph of the invention for use in protecting an animal from a parasitic invertehrate pest. In a further aspect the invention relates to use of a polymorph of the invention in the manufacture of a médicament for protecting an animal from a parasitic invertehrate pest.
In a further aspect the invention provides a method of treating an animal suffering from a parasitic invertehrate pest comprising administering to the animal a pesticidally effective amount of a polymorph of the invention. In a further aspect the invention relates to a polymorph of the invention for use in treating an animal suffering from a parasitic invertehrate pest. In a further aspect the invention relates to use of a polymorph of the invention in the manufacture of a médicament for treating an animal suffering from a parasitic inveijtebrate pest. |
In a further aspect, the invention provides a pharmaceutical composition comprising a polymorph of the invention and a pharmaceutically suitable excipient.
The polymorph ofthe invention may be used alone or in combination with one or more other biologically active ingrédients.
In one aspect the invention provides a combination product comprising a pesticidally effective amount of a component A and a pesticidally effective amount of component B wherein component A is a polymorph of the invention and component B is a compound as described below.
The polymorph of the invention may be used in combination with anthelmintic agents. Such anthelmintic agents include, compounds selected from the macrocyclic lactone class of compounds such as ivermectin, avermectin, abamectin, emamectin, eprinomectin, doramectin, selamectin, moxidectin, nemadectin and milbemycin dérivatives as described in EP- 357460, EP-444964 and EP-594291. Additional anthelmintic agents include semisynthetic and biosynthetic avermectin/milbemycin dérivatives such as those described in US-5015630, WO-9415944 and WO-9522552. Additional anthelmintic agents include the benzimidazoles such as albendazole, cambendazole, fenbendazole, flubendazole, mebendazole, oxfendazole, oxibendazole, parbendazole, and other members of the class. Additional anthelmintic agents include imidazothiazoles and tetrahydropyrimidines such as tetramisole, levamisole, pyrantel pamoate, oxantel or morantel. Additional anthelmintic agents include flukicides, such as triclabendazole and clorsulon and the cestocides, such as praziquantel and epsiprantel.
The polymorphs of the invention may be used in combination with dérivatives and analogues of the paraherquamide/marcfortine class of anthelmintic agents, as well as the antiparasitic oxazolines such as those disclosed in US-5478855, US- 4639771 and DE19520936.
The polymorphs of the invention may be used in combination with dérivatives and analogues of the general class of dioxomorpholine antiparasitic agents as described in WO9615121 and also with anthelmintic active cyclic depsipeptides such as those described in WO-9611945, WO-9319053, WO- 9325543, EP-626375, EP-382173, WO-9419334, EP382173, and EP-50353|8. |
The polymorphs of the invention may be used in combination with other ectoparasiticides; for example, fipronil; pyrethroids; organophosphates; insect growth | i regulators such as lufenuron; ecdysone agonists such as tebufenozide and the like; neonicotinoids such as imidacloprid and the like.
The polymorphs of the invention may be used in combination with terpene alkaloids, for example those described in International Patent Application Publication Numbers WO95/19363 or WO04/72086, particularly the compounds disclosed therein.
Other examples of such biologically active compounds that the polymorphs of the invention may be used in combination with include but are not restricted to the following:
Organophosphates: acephate, azamethiphos, azinphos-ethyl, azinphos- methyl, bromophos, bromophos-ethyl, cadusafos, chlorethoxyphos, chlorpyrifos, chlorfenvinphos, chlormephos, demeton, demeton-S-methyl, demeton-S-methyl sulphone, dialifos, diazinon, dichlorvos, dicrotophos, dimethoate, disulfoton, ethion, ethoprophos, etrimfos, famphur, fenamiphos, fenitrothion, fensulfothion, fenthion, flupyrazofos, fonofos, formothion, fosthiazate, heptenophos, isazophos, isothioate, isoxathion, malathion, methacriphos, methamidophos, methidathion, methyl- parathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, paraoxon, parathion, parathion-methyl, phenthoate, phosalone, phosfolan, phosphocarb, phosmet, phosphamidon, phorate, phoxim, pirimiphos, pirimiphos- methyl, profenofos, propaphos, proetamphos, prothiofos, pyraclofos, pyridapenthion, quinalphos, sulprophos, temephos, terbufos, tebupirimfos, tetrachlorvinphos, thimeton, triazophos, trichlorfon, vamidothion.
Carbamates: alanycarb, aldicarb, 2-sec-butylphenyl methylcarbamate, benfiiracarb, carbaryl, carbofuran, carbosulfan, cloethocarb, ethiofencarb, fenoxycarb, fenthiocarb, furathiocarb, HCN-801, isoprocarb, indoxacarb, methiocarb, methomyl, 5-methyl-mcumenylbutyryl(methyl)carbamate, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, UC-51717.
Pyrethroids: acrinathin, allethrin, alphametrin, 5-benzyl-3-furylmethyl (E) -(1 R)-cis2,2-dimethyl-3-(2-oxothiolan-3-ylidenemethyl)cyclopropanecarboxylate, bifenthrin, beta cyfluthrin, cyfluthrin, a-cypermethrin, beta -cypermethrin, bioallethrin, bioallethrin((S)cyclopentylisomer), bioresmethrin, bifenthrin, NCI-85193, cycloprothrin, cyhalothrin, cythithrin, cyphenothrin, deltanjethrin, empenthrin, esfenvalerate, ethofenprox, fcnfluthyin, fenpropathrin, fenvalerate, flucythrinate, flumethrin, fluvalinate (D isomer), imiprothrin, cyhalothrin, lambda-cyhalothrin, permethrin, phenothrin, prallethrin, pyrethrins (natural products), resmethrin, tetrametlirin, transfluthrin, theta-cypermethrin, silafluofen, t- | fluvalinate, tefluthrin, tralometlîrm, Zeta-cypermethrin. i
Arthropod growth regulators: a) chitin synthesis inhibitors: benzoylureas: chlorfluazuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron, triflumuron, buprofezin, diofenolan, hexythiazox, etoxazole, chlorfentazine; b) ecdysone antagonists: halofenozide, methoxyfenozide, tebufenozide; c) juvenoids: pyriproxyfen, methoprene (including S-methoprene), fenoxycarb; d) lipid biosynthesis inhibitors: spirodiclofen.
Other antiparasitics: acequinocyl, amitraz, AKD-1022, ANS-118, azadirachtin, Bacillus thuringiensis, bensultap, bifenazate, binapacryl, bromopropylate, BTG-504, BTG505, camphechlor, cartap, chlorobenzilate, chlordimeform, chlorfenapyr, chromafenozide, clothianidine, cyromazine, diacloden, diafenthiuron, DBI-3204, dinactin, dihydroxymethyldihydroxypyrrolidine, dinobuton, dinocap, endosulfan, ethiprole, ethofenprox, fenazaquin, flumite, ΜΊΊ- 800, fenpyroximate, fluacrypyrim, flubenzimine, flubrocythrinate, flufenzine, flufenprox, fluproxyfen, halofenprox, hydramethylnon, IKI-220, kanemite, NC-196, neem guard, nidinorterfuran, nitenpyram, SD-35651, WL-108477, pirydaryl, propargite, protrifenbute, pymethrozine, pyridaben, pyrimidifen, NC-1111, R195,RH-0345, RH-2485, RYI-210, S-1283, S-1833, SI-8601, silafluofen, silomadine, spinosad, tebufenpyrad, tetradifon, tetranactin, thiacloprid, thiocyclam, thiamethoxam, tolfenpyrad, triazamate, triethoxyspinosyn, trinactin, verbutin, vertalec, YI-5301.
Fungicides: acibenzolar, aldimorph, ampropylfos, andoprim, azaconazole, azoxystrobin, benalaxyl, benomyl, bialaphos, blasticidin-S, Bordeaux mixture, bromuconazole, bupirimate, carpropamid, captafol, captan, carbendazim, chlorfenazole, chloroneb, chloropicrin, chlorothalonil, chlozolinate, copper oxychloride, copper salts, cyflufenamid, cymoxanil, cyproconazole, cyprodinil, cyprofuram, RH-7281, diclocymet, diclobutrazole, diclomezine, dicloran, difenoconazole, RP-407213, dimethomorph, domoxystrobin, diniconazole, diniconazole-M, dodine, edifenphos, epoxiconazole, famoxadone, fenamidone, fenarimol, fenbuconazole, fencaramid, fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fluazinam, fludioxonil, flumetover, flumorf/flumorlin, fentin hydroxide, fluoxastrobin, fluquinconazole, flusilazole, flutolanil, flutriafol, folpet, fosetylaluminium, furalaxyl, furametapyr, hexalonazole, ipconazole, iprobenfos, iprodione, isoprothiolane, kasugamycin, krsoxim-methyl, mancozeb, maneb, mefenoxam, mepronil, metalaxyl, metconazole, metominostrobin/fenominostrobin, metrafenone, myclobutanil, neoasozin, nicobifen, orysastrobin, oxadixyl, penconazole, pencycuron, probenazole, prochloraz, propamocarb, propioconazole, proquinazid, prothioconazole, pyrifenox, pyraclostrobin, pyrimethanil, pyroquilon, quinoxyfen, spiroxamine, sulfur, tebuconazole, tetrconazole, thiabendazole, thifluzamide, thiophanate-methyl, thiram, tiadinil, triadimefon, triadimenol, tricyclazole, trifloxystrobin, triticonazole, validamycin, vinclozin.
Biological agents: Bacillus thuringiensis ssp aizawai, kurstaki, Bacillus thuringiensis delta endotoxin, baculovirus, entomopathogenic bacteria, virus and fungi.
Bactéricides: chlortetracycline, oxytetracycline, streptomycin.
Other biological agents: enrofloxacin, febantel, penethamate, moloxicam, cefalexin, kanamycin, pimobendan, clenbuterol, omeprazole, tiamulin, benazepril, pyriprole, cefquinome, florfenicol, buserelin, cefovecin, tulathromycin, ceftiour, carprofen, metaflumizone, praziquarantel, triclabendazole.
When used in combination with other active ingrédients, the polymorphs of the invention are preferably used in combination with imidacloprid, enrofloxacin, praziquantel, pyrantel embonate, febantel, penethamate, moloxicam, cefalexin, kanamycin, pimobendan, clenbuterol, fipronil, ivermectin, omeprazole, tiamulin, benazepril, milbemycin, cyromazine, thiamethoxam, pyriprole, deltamethrin, cefquinome, florfenicol, buserelin, cefovecin, tulathromycin, ceftiour, selamectin, carprofen, metaflumizone, moxidectin, methoprene (including S-methoprene), clorsulon, pyrantel, amitraz, triclabendazole, avermectin, abamectin, emamectin, eprinomectin, doramectin, selamectin, nemadectin, albendazole, cambendazole, fenbendazole, flubendazole, mebendazole, oxfendazole, oxibendazole, parbendazole, tetramisole, levamisole, pyrantel pamoate, oxantel, morantel, triclabendazole, epsiprantel, fipronil, lufenuron, ecdysone or tebufenozide; more preferably, enrofloxacin, praziquantel, pyrantel embonate, febantel, penethamate, moloxicam, cefalexin, kanamycin, pimobendan, clenbuterol, omeprazole, tiamulin, benazepril, pyriprole, cefquinome, florfenicol, buserelin, cefovecin, tulathromycin, ceftiour, selamectin, carprofen, moxidectin, clorsulon, pyrantel, eprinomectin, doramectin, selamectin, nemadectin, albendazole, cambendazole, fenbendazole, flubendazole, mebendazole, oxfendazole, oxibendazole, parbendazole, tetramisole, levamisole, pyrantel pamoate, oxantel, morantel, triclabendazole, epsiprantel, lufenuron or ecdysone; even more preferably, enrofloxacin, praziquantel, pyrantel embonate, febantel, penethamate, moloxicam, cefalexin, kanamycin, pimobendan, clenbuterol, omeprazole, tiamulin, benazepril, pyriprole, cefquinome, florfenicol, buserelin, cefovecin, tulathromycin, ceftiour, selamectin, carprofen, moxidectin, clorsulon or pyrantel.
Of particular note is a combination where the additional active ingrédient has a different site of action from the polymorph of the invention. In certain instances, a combination with at least one other parasitic invertebrate pest control active ingrédient having a similar spectrum of control but a different site of action will be particularly advantageous for résistance management. Thus, a combination product of the invention may comprise a pesticidally effective amount of a polymorph of the invention and pesticidally effective amount of at least one additional parasitic invertebrate pest control active ingrédient having a similar spectrum of control but a different site of action.
One skilled in the art recognizes that because in the environment and under physiological conditions salts of Chemical compounds are in equilibrium with their corresponding non sait forms, salts share the biological utility of the non sait forms.
Thus a wide variety of salts of polymorphs of the invention (and active ingrédients used in combination with the active ingrédients of the invention) may be useful for control of invertebrate pests and animal parasites. Salts include acid-addition salts with inorganic or organic acids such as hydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic, butyric, fumaric, lactic, maleic, malonic, oxalic, propionic, salicylic, tartaric, 4-toluenesulfonic or valeric acids. The polymorphs of the invention also include N-oxides. Accordingly, the invention comprises combinations of polymorphs of the invention including N-oxides and salts thereof and an additional active ingrédient including N-oxides and salts thereof.
The compositions for use in animal health may also contain formulation auxiliaries and additives, known to those skilled in the art as formulation aids (some of which may be considered to also function as solid diluents, liquid diluents or surfactants). Such formulation auxiliaries and additives may control: pH (buffets), foaming during processing (antifoams such polyorganosiloxanes), sédimentation of active ingrédients (suspending agents), viscosity (thixotropic thickeners), in-container microbial growth (antimicrobiais), product freezing (antifreezes), color (dyes/pigment dispersions), wash-off (film formers or stickers), évaporation (évaporation retardants), and other formulation attributes. Film formers include, foi| example, polyvinyl acétates, polyvinyl acetate copolyn|ers, polyvinylpyrrolidone-vinyl acetate copolymer, polyvinyl alcohols, polyvinyl alcohol copolymers and waxes. Examples of formulation auxiliaries and additives include those listed in McCutcheon 's Volume 2: Functional Materials, annual International and North American éditions published by McCutcheon's Division, The Manufacturing Confectioner Publishing Co.; and PCT Publication WO 03/024222.
The polymorphs of the invention can be applied without other adjuvants, but most often application will be of a formulation comprising one or more active ingrédients with suitable carriers, diluents, and surfactants and possibly in combination with a food depending on the contemplated end use. One method of application involves spraying a water dispersion or refined oil solution of the combination products. Compositions with spray oils, spray oil concentrations, spreader stickers, adjuvants, other solvents, and synergists such as piperonyl butoxide often enhance compound efficacy. Such sprays can be applied from spray containers such as a can, a bottle or other container, either by means of a pump or by releasing it from a pressurized container, e.g., a pressurized aérosol spray can. Such spray compositions can take various forms, for example, sprays, mists, foams, fumes or fog. Such spray compositions thus can further comprise propellants, foaming agents, etc. as the case may be. Of note is a spray composition comprising a pesticidally effective amount of a compound of the invention and a carrier. One embodiment of such a spray composition comprises a pesticidally effective amount of a compound of the invention and a propellant. Représentative propellants include, but are not limited to, methane, ethane, propane, butane, isobutane, butene, pentane, isopentane, neopentane, pentene, hydrofluorocarbons, chlorofluorocarbons, dimethyl ether, and mixtures of the foregoing. Of note is a spray composition (and a method utilizing such a spray composition dispensed from a spray container) used to control at least one parasitic invertebrate pest selected from the group consisting of mosquitoes, black flies, stable Aies, deer flies, horse flies, wasps, yellow jackets, homets, ticks, spiders, ants, gnats, and the like, including individually or in combinations.
The controlling of animal parasites includes controlling external parasites that are parasitic to the surface of the body of the host animal (e.g., shoulders, armpits, abdomen, inner part of the thighs) and internai parasites that are parasitic to the inside of the body of the host animal (e.g., stomach, intestine, lung, veins, under the skin, lymphatic tissue). External parasitic or disease transmitting pests include, for example, chiggers, ticks, lice, mosquitoes^ flies, mites and fleas. Internai parasites include heartwtjtrms, hookworms and helminths. The polymorphs of the invention may be particularly suitable for combating external parasitic pests. The polymorphs of the invention may be suitable for systemic and/or non-systeimc control of infestation or infection by parasites on animais.
I i
The polymorphs of the invention may be suitable for combating parasitic invertebrate pests that infest animal subjects including those in the wild, livestock and agricultural ’ working animais. Livestock is the term used to refer (singularly or plurally) to a domesticated animal intentionally reared in an agricultural setting to make produce such as food or fiber, or for its labor; examples of livestock include cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, hens, turkeys, ducks and geese (e.g., raised for méat, milk, butter, eggs, fur, leather, feathers and/or wool). By combating parasites, fatalities and performance réduction (in terms of méat, milk, wool, skins, eggs, etc.) are reduced, so that applying the polymorphs of the invention allows more économie and simple husbandry of animais.
The polymorphs of the invention may be suitable for combating parasitic invertebrate pests that infest companion animais and pets (e.g., dogs, cats, pet birds and aquarium fish), research and experimental animais (e.g., hamsters, guinea pigs, rats and mice), as well as animais raised for/in zoos, wild habitats and/or cireuses.
In an embodiment of this invention, the animal is preferably a vertebrate, and more preferably a mammal, avian or fish. In a particular embodiment, the animal subject is a mammal (including great apes, such as humans). Other mammalian subjects include primates (e.g., monkeys), bovine (e.g., cattle or dairy cows), porcine (e.g., hogs or pigs), ovine (e.g., goats or sheep), equine (e.g., horses), canine (e.g., dogs), feline (e.g., house cats), camels, deer, donkeys, buffalos, antelopes, rabbits, and rodents (e.g., guinea pigs, squirrels, rats, mice, gerbils, and hamsters). Avians include Anatidae (swans, ducks and geese), Cohimbidae (e.g., doves and pigeons), Phasianidae (e.g., partridges, grouse and turkeys), Thesienidae (e.g., domestic chickens), Psittacines (e.g., parakeets, macaws, and parrots), game birds, and ratites (e.g., ostriches).
Birds treated or protected by the polymorphs of the invention can be associated with either commercial or noncommercial aviculture. These include Anatidae, such as swans, geese, and ducks, Cohimbidae, such as doves and domestic pigeons, Phasianidae, such as partridge, grouse and turkeys, Thesienidae, such as domestic chickens, and Psittacines, such as parakeets, macaw|s and parrots raised for the pet or collecter market, amoyg others.
For purposes of the présent invention, the term fish is understood to include without limitation, the Teleosti grouping of fish, i.e., teleosts. Both the Salmoniformes order (which includes the jSalmonidae family) and the Perciformes order (which includes the Centrarchidae family) are contained within the Teleosti grouping. Examples of potential fish récipients include the Salmonidae, Serranidae, Sparidae, Cichlidae, and Centrarchidae, among others.
Other animais are also contemplated to benefit from the inventive methods, including marsupials (such as kangaroos), reptiles (such as farmed turtles), and other economically
I important domestic animais for which the inventive methods are safe and effective in treating or preventing parasite infection or infestation.
Examples of parasitic invertebrate pests controlled by administering a pesticidally effective amount of the polymoiphs of the invention to an animal to be protected include 5 ectoparasites (arthropods, acarines, etc.) and endoparasites (helminths, e.g., nematodes, trematodes, cestodes, acanthocephalans, etc.).
The disease or group of diseases described generally as helminthiasis is due to infection of an animal host with parasitic worms known as helminths. The term 'helminths' is meant to include nematodes, trematodes, cestodes and acanthocephalans. Helminthiasis is a 10 prévalent and serions économie problem with domesticated animais such as swine, sheep, horses, cattle, goats, dogs, cats and poultry.
Among the helminths, the group of worms described as nematodes causes widespread and at times serious infection in various species of animais.
Nematodes that are contemplated to be treated by the polymorphe of the invention 15 include, without limitation, the following généra: Acanthocheilonema, Aelurostrongylus, Ancylostoma, Angiostrongylus, Ascaridia, Ascaris, Brugia, Bunostomum, Capillaria, Chabertia, Cooperia, Crenosoma, Dictyocaulus, Dioctophyme, Dipetalonema, Diphyllobothrium, Dirofilaria, Dracunculus, Enterobius, Filaroides, Haemonchus, Heterakis, Lagochilascaris, Loa, Mansonella, Muellerius, Necator, Nematodirus,
Oesophagostomum, Ostertagia, Oxyuris, Parafilaria, Parascaris, Physaloptera, Protostrongylus, Setaria, Spirocerca, Stephanofilaria, Strongyloides, Strongylus, Thelazia, Toxascaris, Toxocara, Trichinella, Trichonema, Trichostrongylus, Trichuris, Uncinaria and Wuchereria.
I
Of the above, the most common généra of nematodes infecting the animais referred 25 to above are Haemonchus, Trichostrongylus, Ostertagia, Nematodirus, Cooperia, Ascaris, Bunostomum, Oesophagostomum, Chabertia, Trichuris, Strongylus, Trichonema, j Dictyocaulus, Capillaria, Heterakis, Toxocara, Ascaridia, Oxyuris, Ancylostoma, Uncinaria, Toxascaris and Parascaris. Certain of these, such as Nematodirus, Cooperia and Oesophagostomum attack primarily the intestinal tract while others, such as Haemonchus and Ostertagia, are more prévalent in the stomach while others such as Dictyocaulus are found in the lungs. Still other parasites may be located in other tissues such as the heart and blood vessels, subcutaneous and lymphatic tissue and the like.
Trematodes that are contemplated to be treated by the invention and by the inventive methods include, without limitation, the following généra: Alaria, Fasciola, Nanophyetus,
Opisthorchis, Paragonimus and Schistosoma.
Cestodes that are contemplated to be treated by the invention and by the inventive methods include, without limitation, the following généra: Diphyllobothrium, Diplydium, Spirometra and Taenia.
The most common généra of parasites of the gastrointestinal tract of humans are Ancylostoma, Necator, Ascaris, Strongy hides, Trichinella, Capillaria, Trichuris and Enterobius. Other medically important généra of parasites which are found in the blood or other tissues and organs outside the gastrointestinal tract are the filarial worms such as Wuchereria, Brugia, Onchocerca and Loa, as well as Dracunculus and extra intestinal stages of the intestinal worms Strongyloides and Trichinella.
Numerous other helminth généra and species are known to the art, and are also contemplated to be treated by the polymorphs of the invention. These are enumerated in great detail in Textbook of Veterinary Clinical Parasitology, Volume 1, Helminths, E. J. L. Soulsby, F. A. Davis Co., Philadelphia, Pa.; Helminths, Arthropods and Protozoa, (6thEdition of Monnig's Veterinary Helminthology and Entomology), E. J. L. Soulsby, Williams and Wilkins Co., Baltimore, Md.
The polymorphs of the invention may be effective against a number of animal ectoparasites (e.g., arthropod ectoparasites of mammals and birds).
Insect and acarine pests include, e.g., biting insects such as flies and mosquitoes, mites, ticks, lice, fleas, true bugs, parasitic maggots, and the like.
Adult flies include, e.g., the holm fly or Haematobia irritons, the horse fly or Tabanus spp., the stable fly or Stomoxys calcitrans, the black fly or Simulium spp., the deer fly or Chrysops spp., the louse fly or Melophagus ovinus, and the tsetse fly or Glossina spp. Parasitic fly maggots include, e.g., the bot fly (Oestrus ovis and Cuterebra spp.), the blow fly or Phaenicia spp., the screwworm or Cochliomyia hominivorax, the cattle grub or Hypoderma spp., the fleeceworm and the Gastrophilus of horses. Mosquitoes include, for example, Culex spp., Anopheles spp. and^eJej spp.
Mites include Mesostigmalphatalpha spp. e.g., mesostigmatids such as the chicken mite, Dermalphanyssus galphallinalphae·, itch or scab mites such as Sarcoptidae spp. for example, Salpharcoptes scalphabiei·, mange mites such as Psoroptidae spp. including
Chorioptes bovis and Psoroptes ovis; chiggers e.g., Trombiculidae spp. for example the
North American chigger, Trombiculalpha alphalfreddugesi.
Ticks include, e.g., soft-bodied ticks including Argasidae spp. for example Argalphas 5 spp. and Omithodoros spp.; hard-bodied ticks including Ixodidae spp., for example Rhipicephalphalus sanguineus, Dermacentor variabilis, Dermacentor andersoni, Amblyomma americanum, Ixodes scapularis and other Rhipicephalus spp. (including the former Boophilus généra).
Lice include, e.g., sucking lice, e.g., Menopon spp. and Bovicola spp.; biting lice, 10 e.g., Haematopinus spp., Linognathus spp. and Solenopotes spp.
Fleas include, e.g., Ctenocephalides spp., such as dog flea (Ctenocephalides canis) and cat flea (Ctenocephalides felis); Xenopsylla spp. such as oriental rat flea (Xenopsylla cheopis); and Pulex spp. such as human flea (Pulex irritons).
True bugs include, e.g., Cimicidae or e.g., the common bed bug (Cimex lectularius);
Triatominae spp. including triatomid bugs also known as kissing bugs; for example Rhodnius prolixus and Triatoma spp.
Generally, Aies, fleas, lice, mosquitoes, gnats, mites, ticks and helminths cause tremendous losses to the livestock and companion animal sectors. Arthropod parasites also are a nuisance to humans and can vector disease-causing organisme in humans and animais.
Numerous other parasitic invertebrate pests are known to the art, and are also contemplated to be treated by the polymorphs of the invention. These are enumerated in great detail in Medical and Veterinary Entomology, D. S. Kettle, John Wiley AND Sons, I New York and Toronto; Control of Arthropod Pests of Livestock: A Review of Technology, R. O. Drummand, J. E. George, and S. E. Kunz, CRC Press, Boca Raton, Fia.
I 25 The polymorphs of the invention may also be effective against ectoparasites
I including: Aies such as Haematobia (Lyperosià) irritons (hom Ay), Simulium spp. (blackAy), Glossina spp. (tsetse Aies), Hydrotaea irritons (head Ay), Musca autumnalis (face Ay), Musca domestica (house Ay), Morellia simplex (sweat Ay), Tabanus spp. (horse Ay), Hypoderma bovis, Hypoderma lineatum, Lucilia sericata, Lucilia cuprina (green blowAy),
Calliphora spp. (blowAy), Protophormia spp., Oestrus ovis (nasal botAy), Culicoides spp. (midges), Hippobosca equine, Gastrophilus intestinalis, Gastrophilus haemorrhoidalis and
Gastrophilus nasalis’, lice such as Bovicola (Damalinia) bovis, Bovicola equi, Haematopinus asini, Felicola subrostratus, Heterodoxus spiniger, Lignonathus setosus and Trichodectes canis; keds such as Melophagus ovinus, and mites such as Psoroptes spp., Sarcoptes scabei, Chorioptes bovis, Demodex equi, Cheyletiella spp., Notoedres cati, Trombicula spp. and Otodectes cyanotis (ear mites).
Treatments of the invention are by conventional means such as by enterai administration in the form of, for example, tablets, capsules, drinks, drenching préparations, granulates, pastes, boli, feed-through procedures, or suppositories; or by parentéral administration, such as, for example, by injection (including intramuscular, subcutaneous, intravenous, intraperitoneal) or implants; or by nasal administration.
When polymorphs of the invention are applied in combination with an additional biologically active ingrédient, they may be administered separately e.g. as separate compositions. In this case, the biologically active ingrédients may be administered simultaneously or sequentially. Alternatively, the biologically active ingrédients may be components of one composition.
The polymorphs of the invention may be administered in a controlled release form, for example in subcutaneous or orally adminstered slow release formulations.
Typically a parasiticidal composition according to the présent invention comprises a polymorph of the invention, optionally in combination with an additional biologically active ingrédient, or N-oxides or salts thereof, with one or more pharmaceutically or veterinarily acceptable carriers comprising excipients and auxiliaries selected with regard to the intended route of administration (e.g., oral or patenterai administration such as injection) and in accordance with standard practice. In addition, a suitable carrier is selected on the basis of Icompatibility with the one or more active ingrédients in Ithe composition, including such considérations as stability relative to pH and moisture content. Therefore of note are polymorph of the invention for protecting an animal from an invertebrate parasitic pest ^comprising a parasitically effective amount of a polymorph of the invention, optionally in combination with an additional biologically active ingrédient and at least one carrier.
For parentéral administration including intravenous, intramuscular and subcutaneous injection, the polymorphs of the invention can be formulated in suspension, solution or émulsion in oily or aqueous vehicles, and may contain adjuncts such as suspending, stabilizing and/or dispersing agents.
The polymorphs of the invention may also be formulated for bolus injection or continuous infusion. Pharmaceutical compositions for injection include aqueous solutions of water-soluble forms of active ingrédients (e.g., a sait of an active compound), preferably in physiologically compatible buffers containing other excipients or auxiliaries as are known in the art ofpharmaceutical formulation. Additionally, suspensions ofthe active compounds may be prepared in a lipophilie vehicle. Suitable lipophilie vehicles include fatty oils such as sesame oil, synthetic fatty acid esters such as ethyl oleate and triglycérides, or materials such as liposomes.
Aqueous injection suspensions may contain substances that increase the viscosity of the suspension, such as sodium carboxymethyl cellulose, sorbitol, or dextran. Formulations for injection may be presented in unit dosage form, e.g., in ampoules or in multi-dose containers. Alternatively, the active ingrédient may be in powder form for constitution with a suitable vehicle, e.g., stérile, pyrogen-free water, before use.
In addition to the formulations described supra, the polymorphs of the invention may also be formulated as a depot préparation. Such long acting formulations may be administered by implantation (for example, subcutaneously or intramuscularly) or by intramuscular or subcutaneous injection.
The polymorphs of the invention may be formulated for this route of administration with suitable polymeric or hydrophobie materials (for instance, in an émulsion with a pharmacologically acceptable oil), with ion exchange resins, or as a sparingly soluble dérivative such as, without limitation, a sparingly soluble sait.
For administration by inhalation, the polymorphs of the invention can be delivered in the form of an aérosol spray using a pressurized pack or a nebulizer and a suitable propellant, e.g., without limitation, dichlorodifluoromethane, trichlorofluorolnethane, dichlorotetrafluoroethane or carbon dioxide. In the case of a pressurized aérosol, the dosage unit may be controlled by providing a valve to deliver a metered amount.
Capsules and cartridges of, for example, gelatin for use iii an inhaler or insufïlator may be formulated containing a powder mix of the compound and a suitable powder base such as lactose or starch.
The polymorphs of the invention may hâve favourable pharmacokinetic and pharmacodynamie properties providing systemic availability from oral administration and ingestion. Therefore after ingestion by the animal to be protected, parasiticidally effective concentrations of a polymorph of the invention in the bloodstream may protect the treated animal from blood-sucking pests such as fleas, ticks and lice. Therefore of note is a composition for protecting an animal from an invertebrate parasite pest in a form for oral administration (i.e. comprising, in addition to a parasiticidally effective amount of a polymorph of the invention, one or more carriers selected from binders and fillers suitable for oral administration and feed concentrate carriers).
For oral administration in the form of solutions (the most readily available form for absorption), émulsions, suspensions, pastes, gels, capsules, tablets, boluses, powders, granules, rumen-retention and feed/water/lick blocks, the polymorph of the invention can be formulated with binders/fillers known in the art to be suitable for oral administration compositions, such as sugars and sugar dérivatives (e.g., lactose, sucrose, mannitol, sorbitol), starch (e.g., maize starch, wheat starch, rice starch, potato starch), cellulose and dérivatives (e.g., methylcellulose, carboxymethylcellulose, ethylhydroxycellulose), protein dérivatives (e.g., zein, gelatin), and synthetic polymers (e.g., polyvinyl alcohol, polyvinylpyrrolidone). If desired, fabricants (e.g., magnésium stéarate), disintegrating agents (e.g., cross-linked polyvinylpyrrolidinone, agar, alginic acid) and dyes or pigments can be added. Pastes and gels often also contain adhesives (e.g., acacia, alginic acid, bentonite, cellulose, xanthan gum, colloïdal magnésium aluminum silicate) to aid in keeping the composition in contact with the oral cavity and not being easily ejected.
In one embodiment a composition of the présent invention is formulated into a chewable and/or edible product (e.g., a chewable treat or edible tablet). Such a product would ideally hâve a taste, texture and/or aroma favored by the animal to be protected so as to facilitate oral administration of the compounds of the invention.
If the parasiticidal compositions are in the form of feed concentrâtes, the carrier is typically selected from high-performance feed, feed cereals or protein concentrâtes. Such feed concentrate-çontaining compositions can, in addition to the parasiticidal active ingrédients, comprise additives promoting animal health or growth, improving quality of méat from animais for slaughter or otherwise useful to animal husbandry. These additives can include, for example, vitamins, antibiotics, chemotherapeutics, bacteriostats, fungistats, coccidiostats and hormones.
The polymorph of the invention may also be formuiated in rectal compositions such as suppositories or rétention enemas, using, e.g., conventional suppository bases such as cocoa butter or other glycendes.
The formulations for the method of this invention may include an antioxidant, such asBHT (butylated hydroxytoluene). The antioxidant is generally present in amounts of at 0.15 percent (wt/vol). Some of the formulations require a solubilizer, such as oleic acid, to dissolve the active agent, particularly if spinosad is included. Common spreading agents used in these pour-on formulations include isopropyl myristate, isopropyl palmitate, caprylic/capric acid esters of saturated C12-C18 fatty alcohols, oleic acid, oleyl ester, ethyl oleate, triglycérides, silicone oils and dipropylene glycol methyl ether. The pour-on formulations for the method of this invention are prepared according to known techniques. Where the pour-on is a solution, the parasiticide/insecticide is mixed with the carrier or vehicle, using heat and stirring if required. Auxiliary or additional ingrédients can be added to the mixture of active agent and carrier, or they can be mixed with the active agent prior to the addition of the carrier. Pour-on formulations in the form of émulsions or suspensions are similarly prepared using known techniques.
Other delivery Systems for relatively hydrophobie pharmaceutical compounds may be employed. Liposomes and émulsions are well-known examples of delivery vehicles or carriers for hydrophobie drugs. In addition, organic solvents such as dimethylsulfoxide may be used, if needed.
The rate of application required for effective parasitic invertebrate pest control (e.g. pesticidally effective amount) will dépend on such factors as the species of parasitic invertebrate pest to be controlled, the pest's life cycle, life stage, its size, location, time of year, host crop or animal, feeding behavior, mating behavior, ambient moisture, teyiperature, and the like. One skilled in the art can easily détermine the pesticidally effective amount necessary for the desired level of parasitic invertebrate pest control.
In general for veterinary use, the polymorphs of the invention are administered in a pesticidally effective amount to an animal, particularly a homéothermie animal, to be protected from parasitic invertebrate pests.
A pesticidally effective amount is the amount of active ingrédient needed to achieve an observable effect diminishing the occurrence or activity of the target parasitic invertebrate pest. One skilled in the art will appreciate that the pesticidally effective dose can vary for the various compounds and compositions useful for the method of the présent invention, the desired pesticidal effect and duration, the target parasitic invertebrate pest species, the animal to be protected, the mode of application and the like, and the amount needed to achieve a particular resuit can be determined through simple expérimentation.
For oral or parentéral administration to animais, a dose of the compositions of the présent invention administered at suitable intervals typically ranges from about 0.01 mg/kg to aboutlOO mg/kg, and preferably from about 0.01 mg/kg to about 30 mg/kg of animal body weight.
Suitable intervals for the administration of the compositions of the présent invention to animais range from about daily to about yearly. Of note are administration intervals ranging from about weekly to about once every 6 months. Of particular note are monthly adminstration intervals (i.e. administering the compounds to the animal once every month).
The présent invention will now be described by way of the following non-limiting examples and figures, wherein:
FIG. 1 shows the measured powder X-ray diffraction pattern of the polymorph designated Form A(a).
FIG. 2 shows the predicted powder X-ray diffraction pattern of the polymorph designated Form A(a).
FIG. 3 shows a DSC trace of the polymorph designated Form A(a).
FIG. 4 shows the measured powder X-ray diffraction pattern of the polymorph designated Form A(b). | I
FIG. 5 shows a DSC trace of the polymorph designated Form A(b).
FIG. 6 shows the measured powder X-ray diffraction pattern of the hydrate of the
I compound of formula IA.
FIG. 7 shows the predicted powder X-ray diffraction pattern of the hydrate of the compound of formula IA.
I FIG. 8 shows the measured powder X-ray diffraction pattern of the polymorph of the compound of formula IB.
FIG. 9 shows a DSC trace of the polymorph of the compound of formula IB.
FIG. 10 shows the predicted powder X-ray diffraction pattern of the polymorph of the 5 compound of formula IB.
FIG. 11 shows the measured powder X-ray diffraction pattern of the polymorph of the racemate of the compounds of formula IA and ID.
FIG. 12 shows a DSC trace of the polymorph of the racemate of the compounds of formula IA and ID.
FIG. 13 shows a Raman spectra of the polymorph designated Form A(a).
FIG. 14 shows a DSC trace of the polymorph designated Form A(c).
EXAMPLES
1. Préparation of Polymorphs
The compound of formula I was made by the methods described in WO
2011/067272. This résultant solid precipitate and liquid filtrate were analysed by HPLC as indicated in WO 2011/067272. The compound of formula IA was présent in the filtrate and the compound of formula IC in the solid precipitate. When crystallised from the filtrate, the polymorph of Form A(c) was identified by DSC (see FIG. 14).
1 a. Préparation of Form A(a) ।
A purified sample of the compound of formula IA was slurried in dimethyl carbonate for 2 weeks at 25°C after which crystals were isolated and characterised by DSC, powder Xray diffraction and single crystal X-ray diffraction. A measured powder X-ray diffraction pattern for the polymoiph of the compound of formula IA (designated Form A(a)) is shown in FIG 1. The pattern predicted from the single crystal intensity data is show in FIG 2. A DSC trace of of Form A(a) is shown in FIG. 3.
1b. Préparation of Form A(b)
A further sample of the compound of formula IA was subject to slow évaporation at room température from a number of solvents. The sample isolated after évaporation from 20% water/methanol was analysed by DSC and powder X-ray diffraction. A measured powder X-ray diffraction pattern for the polymorph of the compound of formula IA (designated Form A(b)) is shown in FIG 4. A DSC trace of Form A(b) is shown in FIG. 5.
c. Préparation of Form A(h)
A further sample of the compound of formula IA was subject to slow avaporation from a water/ethanol mix. Analysis of the crystals showed that water was incorporated in the structure - with two water molécules and two molécules of the compound of formula IA in the asymmetric unit. This hydrate (designated Form A(h)) was subject to analysis by DSC and TGA as well as powder X-ray diffraction and single crystal X-ray diffraction. A measured powder X-ray diffraction pattern for the hydrate is shown in FIG 6. The pattern predicted from the single crystal intensity data is show in FIG 7.
Id. Préparation of Form B(a) and Form C(a)
Samples of the compounds of formula IB and IC were prepared by dissolving the samples in acetone, filtering the acetone through a 0.2pm syringe filter into a clean vial and leaving the vial in a fume cupboard to allow the acetone to evaporate. The resulting solid samples were analysed by powder X-ray diffraction and DSC. The powder X-ray diffraction patterns for IB and IC were identical. The pattern for the compound of formula IB is shown in FIG. 8. The DSC for this compound is shown in FIG. 9.
Crystals suitable for single crystal X-ray diffraction analysis were grown in a mix of isopropanol/water (80/20). The pattern predicted from the single crystal intensity data is shown in FIG. 10. | le. Préparation of a racemic mixture of the compounds of formula IA and ID
Equal amounts of the compounds of formula IA and ID were dissolved in acetone and then left at room température until the solvent had evaporated. The resulting crystalline solid was characterised by powder X-ray diffraction and DSC. A measured powder X-ray diffraction pattern for the polymorph of the racemate of the compounds of formula IA and
ID is shown in FIG 11. A DSC trace of this polymorph is shown in FIG. 12.
2. Analysis of polymorphs
After préparation, the samples were subject to analysis by powder X-ray diffraction and/or single crystal X-ray diffraction and/or differential scanning calorimetry (DSC) and/or thermal gravimétrie analysis (TGA), as detailed above. The methods used for these analysis techniqes are detailed below:
Powder X-ray diffraction analysis of solid material was carried out using the Bruker D8 powder diffractometer at room température and at relative humidifies above 40%. Samples were mounted in Perspex sample holders and the samples flattened. The sample holder was rotated and X-rays were collected from 4° to 34° 2-theta, with a scan time of 25 to 30 minutes depending on the pattern intensity.
Single crystal intensity data was collected on an Oxford Xcalibar PX Ultra diffractometer using Cu Ka radiation (λ=1.5418 Â) with a graphite monochromator. The crystal was mounted in Paratone N oil at 100K for data collection. The data was solved using the CRYSTALS software package.
DSC was carried out using a Mettler Toledo DSC1. A sample loading of around 5mg was used and this was heated from 25°C to 160°C at a rate of 10°C/minute. The lid of the DSC crucible was pierced to allow the escape of any gas formed during the heating of the sample.
Raman spectroscopy was carried out using a Thermo Scientific DXR Raman microscope: a 780nM Raman laser was focused on the sample on a quartz slide.
3. Stability of polymorphs
A sample of the polymorph designated Form A(c) was stirred in 5 ml dimethyl carbonate for two days. The crystals were isolated, air dried and characterised by DSC and pXRD*. The DSC curve showed a sharp single melting endothLrm with a melting peak at 141°C and the pXRD pattern matched that of Form A(a), indicating that ail of the Form A(c) had converted into Form (A)a.
Although the invention has been described with reference to preferred embodiments and examples thereof, the scope of the présent invention is not limited only to those described embodiments. As will be apparent to persons skilled in the art, modifications and adaptations to the above-described invention can be made without departing from the spirit and scope of the invention, which is defined and circumscribed by the appended claims. Ail publications cited herein are hereby incorporated by reference in their entirety for ail purposes to the same extent as if each individual publication were specifically and individually indicated to be so incorporated by reference.
Claims (15)
- Claims1. A crystalline polymorph of the compound of formula IAIA which has a powder X-ray diffraction pattern comprising at least three 20 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, which has the following lattice parameters: a=5.06 Â ± 0.01 Â, b=18.92 Â ± 0.01 Â, c=24.17 Â ± 0.01 Â, a = 90° ± 0.01 °, β = 90° ± 0.01 °, γ = 90° ± 0.01 ° and volume = 2315Â3 ± 1 Â3.
- 3. The crystalline polymorph of claim 1 or claim 2, which has a melting point of 141 °C ± 2°C.
- 4. A crystalline polymorph of the compound of formula IA, which is a hydrate and which has a powder X-ray diffraction pattern comprising at least three 20 angle values selected from the ^roup consisting of 4.4 ± 0.2, 7.0 ± 0.2, 8.7 ± 0.2, 10.3 ±j 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.
- 5. The crystalline polymorph of claim 4, which has the following lattice parameters: a=8.03 Â ± 0.01 Â, b=16.10 Â ± 0.01 Â, c=20.37 Â ± 0.01 Â, a = 90° ± 0.01 °, β = 97.02° ± 0.01 °, γ = 90° ± 0.010 and volume = 2615Â3 ± 1 Â3.
- 6. A crystalline polymorph of the compound of formula IB or ICwhich has a powder X-ray diffraction pattern comprising at least three 20 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 and5 21.4 ±0.2.
- 7. The crystalline polymorph of claim 6, which has a melting point of 206°C ± 2°C.
- 8. A crystalline polymorph of the racemate of the compounds of formula IA and IDwhich has a powder X-ray diffraction pattern comprising at least three 20 angle values10 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 ± 0.2,116.2 ± 0.2,16.7 ± 0.2,18.4 ± 0.2,19.5 ± 0.2,19.8 ± 0.2,120.3 ±0.2,21.8 ±0.2 and 23.9 ±0.2.
- 9. The crystalline polymorph bf claim 8, which has a melting point of 173°C ± 2°C.
- 10. An agricultural composition comprising a polymorph as claimed in any one of claims 115 to 9 and at least one agriculturally acceptable carrier or diluent.
- 11. The composition of claim 10, which comprises more than one polymorph of the polymorphs defined in any one of claims 1 to 9.J
- 12. The composition of claim 10, which is enriched for a polymorph of the compound of formula IA.
- 13. The composition of claim 12, which is enriched for the polymorph as defined in claims 1 to 3.5
- 14. The composition of any one of claims 10 to 13, which comprises at least one further insecticide or nematicide.
- 15. A method of preventing or controlling insect infection on plants or plant propagation material comprising treating the plant or plant propagation material with an insecticidally effective amount of an agricultural composition as claimed in any one of 10 claims 10 to 14.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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GB1721235.8 | 2017-12-19 |
Publications (1)
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OA19869A true OA19869A (en) | 2021-06-23 |
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