Insect repellents based on tobacco alkaloids in plants
Patent Information
- Application Number
- ES2023738473T
- Authority / Receiving Office
- ES · ES
- Patent Type
- Patents
- Current Assignee / Owner
- Priority Date
- 2022-07-04
- Filing Date
- 2023-07-03
- Publication Date
- 2026-09-14
- Estimated Expiration
- 2043-07-03
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Abstract
Description
Insect repellents based on tobacco alkaloids in plants This description relates in its broadest aspect to the use of a formulation comprising a compound of Formula I for repelling hemipteran insects. A method for repelling hemipteran insects is also provided herein. Agriculture is a key activity for humans, as it satisfies basic needs such as food, clothing, and shelter. Agricultural productivity can be negatively affected by a number of factors, including insect infestations. Insect infestations interfere with crop and plant growth and cause damage to both cultivated and naturally growing plants. This interference and damage can lead to crop failure and prevent plants from reaching maturity. It is estimated that insect infestations destroy at least 30 to 40 percent of global agricultural production, posing a particular threat to agriculture-dependent parts of the world economy. Insects are responsible for two main types of crop damage. First, feeding insects cause direct damage to the plant by eating leaves or by piercing the stem, fruit, or roots. Second, indirect damage can occur when the insect itself causes little or no harm to the plant but transmits a bacterial, viral, or fungal infection to the crop. Whiteflies belong to the order Hemiptera, specifically the family Aleyrodidae. They are considered a major pest for many crops because they cause considerable damage and yield loss. They feed by sucking the sap from their host plants. Being polyphagous, they feed on many different plants, making them a threat to most crops. The two common whitefly species are the tobacco whitefly (Bemisia tabaci) and the greenhouse whitefly (Trialeurodes vaporariorum). Bemisia tabaci is currently recognized as a complex of around 40 cryptic species with a worldwide distribution that can feed on more than 900 plant species, including a wide range of vegetables (tomatoes, eggplants, sweet potatoes, squash, broccoli, cabbage, etc.), but also cotton, tobacco, and ornamentals such as poinsettias, garden roses, lantana, and lilies. The complete life cycle of the whitefly lasts between 15 and 40 days, depending on the host plant and environmental conditions. For example, the number of eggs laid and the survival of immature stages and adults are greatly affected by temperature, with optimal reproductive capacity at around 28-30 degrees Celsius (°C) (Curnutte et al., Annals of the Entomological Society of America, Vol.107, No.5). Whiteflies lay their eggs on the upper and lower sides of leaves. From the hatched egg emerges the first nymphal stage (crawler) and moves along the leaf until it finds a suitable place to begin feeding on the sugar-rich phloem sap. The nymphs will molt into the second, third, and fourth nymphal stages, during which they remain in the same place and continue feeding on the plant. The fourth stage is also called the pupal stage or red nymph stage, from which the adult will emerge (Sani et al., Insects, 2020, 11, 619). Direct damage occurs to the plant when the whitefly feeds. Sucking the sap leaves discolored spots on the leaves. Furthermore, as they feed, they release toxic substances into the phloem, which then spread throughout the plant. This leads to metabolic imbalances that cause a general weakening of the plant, chlorosis, and changes in the flowers and fruit. As for indirect damage, the honeydew excreted by the nymphs allows fungi such as sooty mold to form on the leaves. This mold acts as a barrier and reduces the plant's photosynthetic capacity. Finally, the most serious damage that whiteflies can cause to crops is the transmission of viruses. The B. tabaci complex is known to transmit more than 200 plant viruses. These include TYLCV (tomato yellow leaf curl virus), TYMV (tomato yellow mosaic virus), and cotton leaf curl disease complex viruses. One of the main goals of whitefly control is to prevent viral infection of the crop. Using protective barriers such as netting and covers is a good way to prevent infestations, but these are only suitable for smaller, less mature crops. The use of control agents represents the most effective way to prevent infestation throughout the entire lifespan of a crop. Most pest control agents are synthetic pesticides. Due to the long-term use of such agents, many pests have developed resistance. Resistance is defined as a change in the sensitivity of a pest population to a pesticide, resulting in the failure of proper pesticide application. The intensive use of insecticides over the past few decades to control whiteflies has led to the emergence of populations resistant to various classes of insecticides, such as carbamates, organophosphates, and pyrethroids. In addition to the difficulty of controlling these pests with current pest control agents, there is growing evidence that some of these agents are highly toxic and take many years to biodegrade. Therefore, it is worthwhile to develop a new, natural pest control agent with a different mechanism of action than those already known. Furthermore, natural pest control agents have a low environmental impact and are generally safer and less hazardous for the people who use them. Among natural pest control agents, tobacco plants (Nicotiana genus spp.) have been used for centuries in the form of dried leaves, powder, extracts, or fumigants. However, interest in tobacco has declined due to safety concerns regarding tobacco's main alkaloid, nicotine, and the discovery of more targeted and potent synthetic pesticides. Therefore, there are currently no commercially available tobacco-derived or nicotine-based products. WO 2020 / 260392 describes a formulation comprising an extract of a tobacco plant and / or a formulation comprising a compound of Formula I, in particular anatabine, and the corresponding uses thereof for reducing ectoparasite infestations.The article "Repellency, toxicity, and anti-oviposition of essential oil of Gardenia jasminoides and its four major chemical components against whiteflies and mites", by Wagen, Cai and Hua, in Scientific Reports, 2018, 8, 9375, describes the repellent, insecticidal and anti-oviposition activities of Gardenia jasminoides essential oil extracted with ethanol against Bemisia tabaci and against the adult and nymphal stages of Tetranychus urticae under laboratory and greenhouse conditions. Consequently, there is a clear need to identify more plant-derived compounds that are as effective as synthetic pesticides but are more environmentally friendly, safer, and have a novel mechanism of action, for inclusion in agricultural pest management programs. It is desirable to provide new compounds and formulations that act in ways other than killing insects and, in particular, are active as repellents. The present invention relates to the use of a formulation for repelling or reducing infestations of hemipteran insects, where hemipteran insects are sap-feeding insects. The formulation comprises a compound of Formula I. The compound of Formula I is Formula 1 where R represents hydrogen or C1-C5 alkyl, and represents a single or double bond. According to one aspect of the present invention, a formulation is provided for repelling hemipteran insects. According to another aspect of the present invention, a formulation is provided for reducing hemipteran insect infestation. The formulation comprises a compound of Formula I. The compound of Formula I is Formula 1 where R represents hydrogen or C1-C5 alkyl, and represents a single or double bond. As used in this description, the terms "repel," "repelling effect," or "repellent effect" mean the effect by which insects are forcibly driven away and / or prevented from landing, walking, feeding, or laying eggs on a surface or substance. As used in this description, the term "infestation" refers to the state in which an abnormally high number of insects or other species are present on a surface or substance. As used in the present description, the term "insects" refers to any member of the largest class of the phylum Arthropoda. As used in this description, "hemipteran insect" refers to insects belonging to the taxonomic category commonly called true bugs, which share a common arrangement of sucking mouthparts. Accordingly, the term "hemipteran insects," as used in this description, is intended to define insects that feed on plants by using their sucking and piercing mouthparts to extract sap from a plant. The present invention is described in more detail with reference to the figures in which: Figure 1 shows the repellent effect of anatabine and DEET over a period of 0, 1, 3 and 6 hours. Figure 2 shows the repellent effect of anatabine at three different concentrations over a period of 3 and 6 hours. Figure 3 shows the repellent effect of anatabine, DEET, and methyl benzoate over a period of 0, 6, 24, and 48 hours. Figure 4 shows the mortality of the whitefly after treatment of the leaves with anatabine, DEET and methyl benzoate, compared to the whitefly that was provided with leaves treated with a placebo solution, or without leaves, for a period of 0, 6, 24 and 48 hours. Figure 5 shows the repellent effect of anatabine and DEET over a period of 51, 75 and 123 hours. As described above, the present invention relates to the use of a formulation for repelling or reducing the infestation of hemipteran insects. The use of a formulation comprising a compound from Formula I has shown an improved repellent effect against hemipteran insects, especially whiteflies. In particular, the use of a formulation comprising anatabine has shown an improved repellent effect against hemipteran insects, especially whiteflies. The repellent effect of the formulation according to the invention has been shown to be more potent and longer lasting than that of commonly used chemical agents such as DEET (N,N-diethyl-meta-toluamide). This has the advantage of reducing the amount and frequency with which the formulation must be applied to crops or plants. Furthermore, the repellent effect was found to be more effective than that of methyl benzoate, a naturally occurring, plant-derived compound known in the art to be effective against whiteflies (Mostafiz et al., PLoS ONE 13, 2018). Surprisingly, the repellent effect of the formulation according to the invention has been found to be 100% effective for an extended period without causing damage to crops or plants. The absence of damage to crops or plants is evidence that the effectiveness of the formulation according to the invention is directly attributable to the hemipteran insects being repelled from their food source, rather than the food source being destroyed. This repellent effect has the added advantage of preventing eggs from being laid on the leaves. The combined effect of preventing access to food and oviposition results in a complete repellent effect. This complete repellent effect, which has been shown to last for a surprisingly long period, ultimately results in the disruption of the whitefly life cycle and, consequently, a decrease in the whitefly population in the area where the formulation is applied. It is known that some compounds in tobacco plants, such as nicotine, can provide a defensive barrier against insect infestation. Nicotine is one of the most abundant compounds in a tobacco plant and is reported to be highly toxic to the vast majority of plant-feeding insects. However, whiteflies exhibit significant tolerance to this and other tobacco plant compounds, to the point that they can consume levels of these compounds 40 times higher than other insects when feeding on tobacco plants. Although tobacco plants are a common food source for hemipteran insects, it has been surprisingly discovered that natural compounds in tobacco plants, particularly anatabine, provide a repellent effect against hemipteran insects, especially whiteflies.Advantageously, the use of anatabine and formulations comprising anatabine provides a natural repellent that is highly effective and efficient, while also being more environmentally friendly and safer to use. In one aspect of the present invention, a formulation according to the present invention is provided, wherein the hemipteran insects are sap-feeding insects. Sap-feeding insects feed on tree foliage by ingesting the sap-sucking parts. Sap-feeding insects have haustellate or sucking mouthparts, which form a beak used to pierce the tissue and suck sap from the phloem tissue buried within the leaf. Rich in nutrients, the phloem tissue represents a unique food source for sap-feeding insects that have developed mechanisms to access it. The use of a formulation according to the present invention prevents hemipteran insects from accessing this food source.Advantageously, this protects the food source from damage caused by sap-feeding insects and forces the sap-feeding insects to look for food elsewhere. In an additional embodiment, the use is provided in accordance with the present invention, wherein the hemipteran insect can be a whitefly. In other embodiments of the present invention, hemipteran insects may be selected from the Aleyrodidae family consisting of Aleyrodes proletella, Aleurocanthus spiniferus, Aleurolobus barodensis, Aleurothrixus floccosus, Bemisia tabaci, Bemisia argentifolii, Dialeurodes citri, Parabemisia myricae, Trialeurodes vaporarium or Siphoninus phillyreae. In other embodiments of the present invention, hemipterous insects can be selected from the Aphididae family that consists of Aphis spp., Acyrthosiphon spp., Anuraphis cardui, Aulacorthum solani, Brachycaudus helichrysi, Brevicor y ne brassicae, Ceratovacuna lanigera, Chaetosiphon fragaefolii, Chromaphis juglandicola, Cry ptomyzus ribis, Dysaphis spp, Myzus spp., Eriosoma spp., Hyalopterus arundinis, Lipaphis er y simi, Macrosiphum spp., Melanaphis sacchari, Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis, Nasonovia ribisnigri, Pemphigus spp., Phloeomyzus passerinii, Phorodon humuli, Rhopalosiphum spp., Schizaphis graminum, Tinocallis car y aefoliae, Toxoptera spp., Acizzia spp., Acrida turrita, Acrogonia spp., Aeneolamia spp., Agonoscena spp. Allocaridara malayensis, Amrasca spp., Aonidiella spp., Aphanostigma piri, Arboridia apicalis, Ar y tainilla spp., Aspidiella spp., Aspidiotus spp., Atanus spp., Balclutha spp., Blastopsylla occidentalis, Boreioglycaspis melaleucae, Cacopsylla spp., Calligypona marginata, Carneocephala fulgida, Cercopidae, Ceroplastes spp., Chionaspis tegalensis, Chlorita onukii, Chr y somphalus ficus, Cicadulina mbila, Coccomytilus halli, Coccus spp., Comstockaspis perniciosa, Cr y ptoneossa spp., Ctenar y taina spp., Dalbulus spp., Diaphorina citri, Diaspis spp., Drosicha spp., Dysmicoccus spp., Empoasca spp., Epiacanthus stramineus, Er y throneura spp., Eucalyptolima spp., Euphyllura spp., Euscelis bilobatus, Ferrisia spp., Fiorinia theae, Geococcus coffeae, Glycaspis spp., Heteropsylla cubana, Heteropsylla spinulosa, Homalodisca coagulata, Icer ya spp., Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., Lepidosaphes spp., Macrosteles facifrons, Mahanarva spp., Metcalfiella spp., Nephotettix spp., Nilaparvata lugens, Oncometopia spp., Orthezia praelonga, Pachypsylla spp., Paratrioza spp., Parlatoria spp., Peregrinus maidis, Phenacoccus spp., Phylloxera spp., Pinnaspis aspidistrae, Planococcus spp., Prosopidopsylla flava, Protopulvinaria pyriformis, Pseudaonidia paeoniae, Pseudaulacaspis ssp., Pseudococcus spp., Psyllopsis spp., Psylla spp., Pyrilla spp., Quadraspidiotus spp., Quesada gigas, Rastroccus spp., Saissetia spp., Scaphoideus titanus, Selenaspidus articulatus, Sogata spp., Sogatella furcifera, Sogatodes spp., Stictocephala festina, Tenalaphara malayensis, Tetragonocephela spp., Tomaspis spp., Trioza spp., Typhlocyba spp., Unaspis spp., Viteus vitifoliae, or Zygina spp. In certain other embodiments of the present invention, the hemipteran insects may be selected from the group consisting of Heteroptera insects, such as, among others, Anasa tristis, Boisea spp., Blissus spp., Cavelerius spp., Cletus punctiger, Dasynus piperis, Diconocoris hewetti, Dysdercus spp., Eur. gaster spp., Leptocorisa spp., Leptoglossus hyllopus, Macropes excavatus, Miridae, Pentastomidae, Piesma spp., Pseudacysta persea, Riptortus spp., Rhopalus spp., Scaptocoris castanea, Scotinophora spp., Stephanitis spp., or Togo hemipterus. In some embodiments, the use is provided in accordance with the present invention, where the use may be to repel or reduce the infestation of hemipteran insects of crops or agricultural plants. In some additional embodiments, the use is provided in accordance with the present invention, wherein the crops or agricultural plants may be vulnerable to whitefly infestation and wherein the crops or agricultural plants may be tobacco plants, cereals, legume plants, oilseed plants, Cucurbitaceae plants, fibrous plants, vegetables, fruits or flowers. In other embodiments of the present invention, the crops or agricultural plants may be selected from the group consisting of wheat, barley, rye, oats, corn, rice, sorghum, triticale, pome fruits, stone fruits, soft fruits, apples, grapes, pears, plums, peaches, almonds, pistachios, cherries, berries, strawberries, raspberries, blackberries, bell peppers, red peppers, legumes, beans, lentils, peas, soybeans, oilseed plants, rapeseed, mustard, sunflowers, courgettes, cucumbers, melons, pumpkins, squash, cotton, flax, hemp, jute, citrus fruits, calamondin, citron, citrus hybrids, grapefruit, tangelo, tangor, pomelo, kumquat, lemon, lime, mandarin orange, sour orange, sweet orange, pomelo, satsuma mandarin, spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, peppers, broccoli, cauliflower, sweet potatoes, coffee, flowers, poinsettia, garden rose, lantana, lilies, shrubs, broadleaf trees, evergreen treesconifers or crape myrtle. In some embodiments of the present invention, the crops or agricultural plants can be found at each stage of their life cycle. In further embodiments, the use of the present invention is provided where crops or agricultural plants can be grown in a greenhouse. The warm, humid conditions and abundant food in a greenhouse provide an excellent and stable environment for insect development. Although hemipteran insects, particularly whiteflies, thrive in temperate zones, they are known to readily develop in greenhouses located in climatic zones where conditions would not normally sustain their life cycle. Advantageously, the formulation according to the present invention has been found to be suitable for use in greenhouses.In fact, although synthetic pesticides used in enclosed spaces have serious harmful consequences for workers during and after application, the use of the formulation according to the present invention provides a natural alternative, which is safer for the user and more sustainable for the environment. As detailed above, the use of a formulation is provided to repel or reduce the infestation of hemipteran insects, wherein the formulation comprises a compound of Formula I. Formula 1 Where R represents hydrogen or C1-C5 alkyl, and represents a single or double bond, and where hemipteran insects are insects that feed on sap. In some embodiments of the present invention, in the compound of Formula I, R may represent hydrogen. In some other embodiments of the present invention, in the compound of Formula I, it may represent a double bond. In certain embodiments of the present invention, the compound of Formula I may be anatabine. Anatabine can exist in two enantiomeric forms: S-(-)anatabine and R-(+)anatabine. Accordingly, anatabine can be present in the formulation of the present invention as any one of S-(-)anatabine, R-(+)anatabine, a mixture of S-(-)anatabine and R-(+)anatabine, or a racemate of S-(-)anatabine and R-(+)anatabine. The amount of R-(+)anatabine and S-(-)anatabine can be present in any enantiomeric ratio, meaning in any enantiomeric excess (ee) of (R)-(+)anatabine or S-(-)anatabine. As used in the present description, the term "enantiomeric ratio" of R-(+) anatabine and S-(-) anatabine is intended to mean the weight ratio between R-(+) anatabine and S-(-) anatabine. According to the use of the present invention, the formulation may comprise an enantiomeric ratio between R-(+) anatabine and S-(-) anatabine of 10:90, 20:80, 30:70, 40:60, 60:40, 70:30, 80:20 or 90:10. The enantiomeric ratio of R-(+) anatabine and S-(-) anatabine can be calculated using the following formula: Ratio of R- (+) anatabine and S- (-) anatabine = amount of R- (+) anatabine by weight / amount of S- (-) anatabine by weight If R-(+)anatabine and / or S-(-)anatabine solvates are used, the solvent can be ignored in the ratio calculation. The enantiomeric ratio can be determined in several ways, including, but not limited to, chromatography, polarimetric measurement of the rotation of polarized light, nuclear magnetic resonance spectroscopy, derivatization of a compound using a chiral compound such as Mosher acid followed by chromatography or nuclear magnetic resonance spectroscopy, high-performance liquid chromatography (HPLC), or direct fractional crystallization of the racemate. According to some embodiments of the present invention, the compounds of Formula I may be extracted from tobacco or chemically synthesized. The compounds of Formula I may be extracted from any variety of tobacco plant. As used herein, the term "extract" or "extracted" is intended to mean a substance obtained from, or a process for obtaining a substance from, a natural source. Alternatively, the compounds of Formula I may be chemically synthesized such that the compounds are identical to the naturally occurring compounds. In some embodiments, use is provided in accordance with the present invention, wherein the formulation may comprise a concentrate of the compound of Formula I. According to the use of the present invention, the formulation may comprise the compound of Formula I in an amount of at least 99 percent, at least 95 percent, at least 90 percent, at least 85 percent, at least 80 percent, at least 75 percent, at least 70 percent, at least 65 percent, at least 60 percent, at least 55 percent, at least 50 percent, at least 45 percent, at least 40 percent, at least 35 percent, at least 30 percent, at least 25 percent, at least 20 percent, at least 15 percent, at least 10 percent, at least 5 percent, at least 2.5 percent, at least 2.4 percent, at least 2.3 percent, at least 2.2 percent, at least 2.1 percent, at least 2 percent, at least 1.9 percent, at least 1.8 percent, at least 1.7 percent, at least 1.6 percent, at least 1.5 percent, at least 14 percent, at least 1, 3 percent, at least 1, 2 percent, at least 1, 1 percent, at least 1 percent, at least 0, 9 percent, at least 0, 8 percent, at least 0, 7 percent, at least 0, 6 percent, at least 0, 5 percent, at least 0, 4 percent, at least 0, 3 percent, at least 0, 2 percent or at least 0, 1 percent by weight of the formulation. According to the use of the present invention, the formulation may comprise the compound of Formula I in an amount of not more than 99 percent, not more than 95 percent, not more than 90 percent, not more than 85 percent, not more than 80 percent, not more than 75 percent, not more than 70 percent, not more than 65 percent, not more than 60 percent, not more than 55 percent, not more than 50 percent, not more than 45 percent, not more than 40 percent, not more than 35 percent, not more than 30 percent, not more than 25 percent, not more than 20 percent, not more than 15 percent, not more than 10 percent, not more than 5 percent, not more than 2.5 percent, not more than 2.4 percent, not more than 2.3 percent, not more than 2.2 percent, no more than 2.1 percent, no more than 2 percent, no more than 1.9 percent, no more than 1.8 percent, no more than 1.7 percent, no more than 1.6 percent, no more than 1.5 percent, no more than 1.4 percent, no more than 1,3 percent, not more than 1.2 percent, not more than 1.1 percent, not more than 1 percent, not more than 0.9 percent, not more than 0.8 percent, not more than 0.7 percent, not more than 0.6 percent, not more than 0.5 percent, not more than 0.4 percent, not more than 0.3 percent, not more than 0.2 percent or not more than 0.1 percent by weight of the formulation. According to the use of the present invention, the formulation may comprise the compound of Formula I in an amount of approximately 99 percent, approximately 95 percent, approximately 90 percent, approximately 85 percent, approximately 80 percent, approximately 75 percent, approximately 70 percent, approximately 65 percent, approximately 60 percent, approximately 55 percent, approximately 50 percent, approximately 45 percent, approximately 40 percent, approximately 35 percent, approximately 30 percent, approximately 25 percent, approximately 20 percent, approximately 15 percent, approximately 10 percent, approximately 5 percent, approximately 2.5 percent, approximately 2.4 percent, approximately 2.3 percent, approximately 2.2 percent, approximately 2.1 percent,approximately 2 percent, approximately 1.9 percent, approximately 1.8 percent, approximately 1.7 percent, approximately 1.6 percent, approximately 1.5 percent, approximately 1.4 percent, approximately 1.3 percent, approximately 1.2 percent, approximately 1.1 percent, approximately 1 percent, approximately 0.9 percent, approximately 0.8 percent, approximately 0.7 percent, approximately 0.6 percent, approximately 0.5 percent, approximately 0.4 percent, approximately 0.3 percent, approximately 0.2 percent, or approximately 0.1 percent by weight of the formulation. According to the use of the present invention, the formulation may comprise the compound of Formula I in an amount selected from 1 percent to 99 percent, 2.5 percent to 95 percent, 5 percent to 90 percent, 10 percent to 85 percent, 15 percent to 80 percent, 20 percent to 75 percent, 25 percent to 70 percent, 30 percent to 65 percent, 35 percent to 60 percent, 40 percent to 55 percent, or 45 percent to 50 percent by weight of the formulation. The amount of the compound of Formula I may have any interval between the indicated extremes. According to a further use of the present invention, the formulation may comprise the compound of Formula I in an amount selected from 0.1 percent to 5 percent, from 0.15 percent to 4.9 percent, from 0.2 percent to 4.8 percent, from 0.25 percent to 4.7 percent, from 0.3 percent to 4.6 percent, from 0.35 percent to 4.5 percent, from 0.4 percent to 4.4 percent, from 0.45 percent to 4.3 percent, from 0.5 percent to 4.2 percent, from 0.55 percent to 4.1 percent, from 0.6 percent to 4.0 percent, from 0.65 percent to 3.9 percent, from 0.7 percent to 3.8 percent percent, from 0.75 percent to 3.7 percent, from 0.8 percent to 3.6 percent, from 0.85 percent to 3.5 percent, from 0.9 percent to 3.4 percent, from 0.95 percent to 3.3 percent, from 1 percent to 3.2 percent, from 1.15 percent to 3.1 percent, from 1.2 percent to 3.0 percent, from 1,25 percent to 2.9 percent, 1.3 percent to 2.8 percent, 1.35 percent to 2.7 percent, 1.4 percent to 2.6 percent, 1.45 percent to 2.5 percent, 1.5 percent to 2.4 percent, 1.6 percent to 2.3 percent, 1.7 percent to 2.2 percent, or 1.8 percent to 2.1 percent by weight of the formulation. The amount of the compound of Formula I may have any interval between the extremes indicated. According to some further embodiments of the present invention, the formulation may comprise the compound of Formula I in an amount of 5 percent, 2 percent, 1 percent, or 0.5 percent by weight of the formulation. In certain embodiments according to the present invention, the formulation can be a water-soluble concentrate, an emulsifiable concentrate, an emulsion, a microemulsion, an oil-based suspension concentrate, a fluid suspension, a water-dispersible granule, a water-soluble granule, a wettable powder, a water-soluble powder, a granule, an encapsulated granule, a fine granule, a macrogranule, an aqueous suspension, a microencapsulated suspension, or a microgranule. Advantageously, the formulation of the present invention can be provided in different forms depending on the type of interaction required between the formulation and the crops or agricultural plants. In fact, the provision of different forms of the formulation of the present invention allows for the selection of the most suitable formulation for the intended use to ensure optimal biological efficiency depending on the target crops or agricultural plants. According to the present invention, a formulation is provided that can be diluted in water. The formulation of the present invention can be diluted in water to obtain a finished product. The formulation of the present invention can be provided as a pre-diluted, ready-to-use formulation or as a concentrate intended for dilution before application. Advantageously, the pre-diluted, ready-to-use formulation can be applied to small agricultural plants or crops. More advantageously, the formulation according to the present invention can be diluted just before application, allowing the user to adjust the dilution ratio of the formulation to be applied to the crops or agricultural plants according to the intended purpose of the application. According to the present invention, the formulation is provided for use wherein the dilution ratio of the formulation with water can be selected from 1:1, 1:2, 1:3, 1:4, 1:5, 1:6, 1:7, 1:8, 1:9, 1:10, 1:15, 1:20, 1:25, 1:30, 1:35, 1:40, 1:45, 1:50, 1:55, 1:60, 1:65, 1:70, 1:75, 1:80, 1:85, 1:90, 1:95, 1:100, 1:150, 1:200, 1:250, 1:300, 1:350, 1:400, 1:450, 1:500, 1:600, 1:700, 1:800, 1:900, or 1:1000. According to the present invention, the use of the diluted formulation is provided wherein the diluted formulation comprises the compound of Formula I in an amount of at least 0.1 percent, at least 0.2 percent, at least 0.3 percent, at least 0.4 percent, at least 0.5 percent, at least 0.6 percent, at least 0.7 percent, at least 0.8 percent, at least 0.9 percent, at least 1 percent, at least 1.1 percent, at least 1.2 percent, at least 1.3 percent, at least 1.4 percent, at least 1.5 percent, at least 1.6 percent, at least 1.7 percent, or at least 1.8 percent by weight of the diluted formulation. According to the present invention, the use of the diluted formulation is provided wherein the diluted formulation comprises the compound of Formula I in an amount of not more than 20 percent, not more than 19 percent, not more than 18 percent, not more than 17 percent, not more than 16 percent, not more than 15 percent, not more than 14 percent, not more than 13 percent, not more than 12 percent, not more than 11 percent, not more than 10 percent, not more than 9 percent, not more than 8 percent, not more than 7 percent, not more than 6 percent, not more than 5 percent, not more than 4 percent or not more than 3 percent by weight of the diluted formulation. According to the present invention, the use of the diluted formulation is provided, wherein the diluted formulation comprises the compound of Formula I in an amount of approximately 0.1 percent to approximately 20 percent, approximately 0.2 percent to approximately 19 percent, approximately 0.3 percent to approximately 18 percent, approximately 0.4 percent to approximately 17 percent, approximately 0.5 percent to approximately 16 percent, approximately 0.6 percent to approximately 15 percent, approximately 0.7 percent to approximately 14 percent, approximately 0.8 percent to approximately 13 percent, approximately 0.9 percent to approximately 12 percent, approximately 1 percent to approximately 11 percent, approximately 1.1 percent to approximately 10 percent, approximately 1.2 percent to approximately 9 percent,from approximately 1.3 percent to approximately 8 percent, from approximately 1.4 percent to approximately 7 percent, from approximately 1.5 percent to approximately 6 percent, from approximately 1.6 percent to approximately 5 percent, from approximately 1.7 percent to approximately 4 percent, or from approximately 1.8 percent to approximately 3 percent by weight of the diluted formulation. In another embodiment of the present invention, the diluted formulation is provided for use, wherein the diluted formulation comprises the compound of Formula I in an amount of less than approximately 10 percent by weight of the diluted formulation. In a further embodiment of the present invention, the diluted formulation is provided for use, wherein the diluted formulation comprises the compound of Formula I in an amount of approximately 5 percent by weight of the diluted formulation. It has been surprisingly demonstrated that at a concentration of less than 10 percent, the formulation does not cause damage to crops or plants. In further embodiments of the present invention, a formulation is provided for application to crops or agricultural plants by coating, spraying, soaking, or irrigation. Advantageously, the choice of application method can be targeted to different families of hemipteran insects. For example, a method with minimized air displacement that deposits closer to the leaves may be more suitable for flying insects, such as whiteflies. In some embodiments of the present invention, the use of a formulation is provided, wherein the formulation can be applied to agricultural crops or plants 1, 2, 3, 4, 5 or 6 times within a 24-hour period. According to the present invention, a formulation is provided for use, wherein the formulation can be applied to agricultural crops or plants at a frequency of daily, every two days, every five days, weekly, every fortnight (14 days), or monthly. Any application frequency can be combined with any of the aforementioned application times within a 24-hour period. According to the present invention, a formulation is provided for use wherein the formulation can be applied routinely, on a scheduled basis, or following evaluation after each application. According to the present invention, a formulation is provided for use, wherein the formulation can be applied for the early detection of insects or after the manifestation of an infestation. Alternatively, the formulation according to the present invention can be used prophylactically before the presence of insects is detected or before the manifestation of an infestation. According to the present invention, a formulation is provided for application during the cooler periods of the day, such as morning, afternoon, or evening. Advantageously, applying the formulation according to the present invention during the cooler periods of the day has been found to reduce the likelihood of evaporation, thus maintaining an effective concentration when applied to crops or agricultural plants. According to the present invention, the use of a formulation is provided, wherein the formulation can be applied to crops or agricultural plants for at least 65 days, at least 60 days, at least 55 days, at least 50 days, at least 45 days, or at least 40 days, or at least 35 days, or at least 30 days, or at least 25 days, or at least 20 days. According to the present invention, the use of a formulation is provided, wherein the formulation can be applied to agricultural crops or plants for no more than 65 days, no more than 60 days, no more than 55 days, no more than 50 days, no more than 45 days, or no more than 40 days. Advantageously, the formulation according to the present invention can be applied at a predetermined frequency for a period of time shorter than, equal to, or longer than the duration of the life cycle of hemipteran insects. More advantageously, the formulation according to the present invention can be applied at a predetermined frequency for a period of time equal to the duration of the life cycle of the whitefly. Consequently, the formulation according to the present invention can be applied for a period of at least 40 days. In accordance with another aspect of the present invention, a method for repelling hemipteran insects is provided, comprising: preparing a concentrated formulation comprising a compound of Formula I, preferably anatabine; diluting the formulation in water to a predetermined dilution ratio or concentration; and applying the diluted formulation to crops or agricultural plants, preferably by spraying. The present invention is further described in, but not limited to, the following examples: Example 1: Comparative study of the repellent effect of anatabine and DEET. The repellent effect of anatabine on adult whiteflies was evaluated in a comparative study that compared the repellent effect of anatabine with the standard synthetic pesticide DEET and a placebo control in which the leaves were treated with solvent only. For the purposes of the study, a tube test was performed using anatabine and DEET solutions prepared according to Table 1. Table 1: Anatabine DEET solutions. For the purposes of the study, leaf discs were immersed for a total of 30 seconds in the prepared solutions and allowed to dry for 10 minutes at room temperature. Subsequently, the leaf discs were placed at the bottom of glass tubes, and a minimum of 20 adult whiteflies were introduced into the tubes. The repellent effect of both anatabine and DEET was measured at different time points: after 1, 3, and 6 hours. The repellent effect of both anatabine and DEET is shown in Table 2 and was calculated by counting the number of whiteflies landing on a leaf compared to the placebo control, using Abbott's formula: Repellent effect = 1 - (Number of whiteflies on a "placebo control" leaf / Number of whiteflies on a "treated" leaf) * 100. The placebo control defines the initial value, with respect to which the repellent effect is calculated according to the formula above. Table 2: Relevant effect of anatabine DEET. The comparative study found that the repellent effect of anatabine was greater than 80% during the 6-hour evaluation period, while the repellent effect of DEET decreased by almost 40% (to around 50%) after 6 hours (Figure 1). Example 2: Study of the repellent effect of anatabine with respect to its concentration. The repellent effect of anatabine on the adult whitefly was evaluated in a study aimed at optimizing the concentration of anatabine. For the purposes of the study, a tube test was performed using anatabine solutions at three different concentrations, prepared according to Table 3. The placebo control defines the reference value, against which the repellent effect is then calculated. Table 3: Anatabine solutions at three different concentrations. For the purposes of the study, the leaf discs were immersed for a total of 30 seconds in the prepared solutions and allowed to dry for 10 minutes at room temperature. Subsequently, the leaf discs were placed at the bottom of glass tubes, and a minimum of 20 adult whiteflies were introduced into the tubes. The repellent effect of anatabine at three different concentrations was measured at different time points: after 1 hour, 3 hours, and 6 hours. The repellent effect of anatabine at different concentrations is shown in Table 4. Table 4: Repellent effect of anatabine at three different concentrations. The repellent effect of anatabine was maintained at 100% regardless of the anatabine concentration (Figure 2); however, it was also observed that the leaves were not damaged by anatabine at concentrations of 5% or lower. Example 3: Comparative study of the repellent effect of anatabine, DEET and methyl benzoate. The repellent effect of anatabine on adult whiteflies was evaluated in a comparative study designed to compare the repellent effect of anatabine with DEET and methyl benzoate. DEET is a standard synthetic pesticide, while methyl benzoate is a plant-derived organic compound that has been reported to have repellent and insecticidal properties, particularly against whiteflies. For the purposes of this study, a tube test was conducted using solutions of anatabine, DEET, and methyl benzoate, prepared according to Table 5. A concentration of 5% was chosen based on the results of Example 2. The repellent effect of anatabine, DEET, and methyl benzoate was evaluated against a placebo control. In the placebo control, the leaves were treated with solvent only. The placebo control defines the reference value, against which the repellent effect is then calculated. Table 5: Anatabine DEET solutions. For the purposes of the study, the leaf discs were immersed for a total of 30 seconds in the prepared solutions and allowed to dry for 10 minutes at room temperature. Subsequently, the leaf discs were placed at the bottom of glass tubes, and a minimum of 20 adult whiteflies were introduced into the tubes. The repellent effect of anatabine, DEET, and methyl benzoate was measured at different time points: after 6 hours, 24 hours, and 48 hours. The repellent effect of anatabine, DEET, and methyl benzoate is shown in Table 6. Table 6: Relevant effect of anatabine, DEET, and methyl benzoate. The repellent effect of anatabine remained at 100% throughout the 48-hour evaluation period. In contrast, the repellent effect of methyl benzoate had decreased by almost 25% by the end of the 48-hour evaluation period (Figure 3), and the repellent effect of DEET had decreased to 93%. In addition, the presence and quantity of eggs on the leaves after a 48-hour period were visually assessed and the results are shown in Table 7. Table 7: Presence of eggs on leaves after being treated with anatabine, DEET, methyl benzoate and placebo. No eggs were observed on the leaves treated with the repellents, regardless of the repellent used, but they were clearly visible on the untreated leaves. The study also assessed the whitefly mortality rate during the evaluation period. The results are provided in Table 8. Table 8: Whitefly mortality study comparing leaves treated with anatabine, DEET, and methyl benzoate. The whitefly mortality rate remained below 10% during the evaluation period when the leaves were treated with the placebo. In contrast, when feeding was prevented because the leaves were treated with repellents, the whiteflies began to die within a day. By the end of the 48-hour evaluation period, the whitefly mortality rate on the treated leaves had reached approximately 80%, as shown in Figure 4. To better understand the mortality rate, a whitefly population was also observed without access to leaves during the 48-hour evaluation period. Without access to a food source, the whiteflies began to die after only 24 hours, reaching a mortality rate of 60% after 48 hours. Furthermore, DEET and methyl benzoate were observed to cause severe leaf damage during the 48-hour evaluation period. In contrast, anatabine did not cause any damage during the evaluation period, as shown in Table 9. Table 9: Leaf damage caused by treatment with anatabine DEET methyl benzoate. Example 4: Comparative study of the repellent effect of anatabine and DEET. The repellent effect of anatabine on adult whiteflies was evaluated in a further comparative study that introduced additional whiteflies and freshly treated leaves at established evaluation times. For the purposes of the study, a tube assay was conducted using anatabine and DEET solutions at a concentration of 5% along with a placebo solution, as shown in Table 10. The placebo control defines the baseline value, against which the repellent effect is then calculated. Table 10: Anatabine DEET solutions. Whiteflies were introduced into the tube at infestation times: 48, 72, and 120 hours, and the repellent effect was measured after 3 hours at evaluation times: 51, 75, and 123 hours. The results are shown in Table 11. Table 11: Relevant effect of anatabine DEET Anatabine was shown to have 100% efficacy after 48 hours of treatment, followed by a repellent effect of over 80% for the remaining 5 days (up to 123 hours) of the evaluation period. In contrast, the efficacy of DEET decreased by almost 50% after the first 48 hours and remained below 50% for the remaining 5 days (up to 123 hours) of the evaluation period (Figure 5). The presence of eggs was visually monitored 24 hours after each infestation event. The results are shown in Table 12. Table 12: Presence of eggs on leaves after the leaves have been treated with anatabine, DEET and placebo. The number of eggs observed on leaves treated with anatabine remained low throughout the evaluation period of up to 6 days (144 hours). In contrast, eggs were observed on leaves treated with DEET after only 3 days (72 hours), and the number of eggs was close to that of leaves treated with placebo at the end of the 6-day (144-hour) evaluation period. The invention is defined in the claims; however, a non-exhaustive list of non-limiting aspects is provided below. One or more of the features of these aspects may be combined with one or more features of another aspect described herein. Aspect 1: Use of a formulation to repel or reduce infestation of hemipteran insects, the formulation comprising a compound of Formula I, Formula 1 Where R represents hydrogen or C1-C5 alkyl, and represents a single or double bond, and where hemipteran insects are insects that feed on sap. Aspect 2: Use in accordance with Aspect 1, where hemipteran insects are sap-feeding insects that feed on plants. Aspect 3: Use in accordance with Aspect 1 or Aspect 2, where hemipteran insects are sap-feeding insects that extract sap from a plant. Aspect 4: Use in accordance with Aspects 1 through 3, where the hemipteran insects are whiteflies. Aspect 5: Use in accordance with Aspects 1 through 4, to repel or reduce infestation of hemipteran insects in crops or agricultural plants. Aspect 6: Use in accordance with Aspect 1 to Aspect 5, to repel or reduce whitefly infestation on crops or agricultural plants. Aspect 7: Use in accordance with Aspect 5 or Aspect 6, where crops or agricultural plants are vulnerable to whitefly infestation. Aspect 8: Use in accordance with Aspect 5 to Aspect 7, where the crops or agricultural plants are selected from tobacco plants, cereals, legume plants, oil plants, cucurbit plants, fiber plants, vegetables, fruits, flowers and ornamentals. Aspect 9: Use in accordance with Aspect 5 to Aspect 8, where the crops or agricultural plants are tobacco plants. Aspect 10: Use in accordance with Aspect 5 to Aspect 9, where crops or agricultural plants are grown in a greenhouse. Aspect 11: The use in accordance with Aspect 1 to Aspect 10, where R in the compound of Formula I represents hydrogen. Aspect 12: The use in accordance with Aspect 1 to Aspect 11, where in the compound of Formula I it represents a double bond. Aspect 13: Use in accordance with Aspect 1 through Aspect 12, wherein the compound of Formula I is selected from anatabine, S-(-)anatabine, R-(+)anatabine, a mixture of S-(-)anatabine and R-(+)anatabine, or a racemate of S-(-)anatabine and R-(+)anatabine. Aspect 14: Use in accordance with Aspect 1 through Aspect 13, wherein hemipteran insects are sap-feeding insects that feed on tobacco plants, and wherein the compound of Formula I is anatabine. Aspect 15: Use in accordance with Aspect 1 to Aspect 14, wherein the hemipteran insects are whiteflies, and wherein the compound of Formula I is anatabine. Aspect 16: Use in accordance with Aspect 1 to Aspect 15, wherein the compound of Formula I is extracted from tobacco or chemically synthesized. Aspect 17: Use in accordance with Aspect 1 to Aspect 16, wherein the formulation comprises a concentrate of the compound of Formula I. Aspect 18: Use in accordance with Aspect 1 through Aspect 17, wherein the formulation comprises the compound of Formula I in an amount of at least 99 percent, at least 95 percent, at least 90 percent, at least 85 percent, at least 80 percent, at least 75 percent, at least 70 percent, at least 65 percent, at least 60 percent, at least 55 percent, at least 50 percent, at least 45 percent, at least 40 percent, at least 35 percent, at least 30 percent, at least 25 percent, at least 20 percent, at least 15 percent, at least 10 percent, at least 5 percent, at least 2.5 percent, or at least 1 percent by weight of the formulation.Aspect 19: Use in accordance with Aspect 1 to Aspect 18, wherein the formulation is a water-soluble concentrate, emulsifiable concentrate, microemulsion, oil-based suspension, fluid suspension, water-dispersible granule, water-soluble granule, wettable powder, water-soluble powder, encapsulated granule, macrogranule, aqueous suspension, microencapsulated suspension, or microgranule. Aspect 20: Use in accordance with Aspect 1 to Aspect 19, where the formulation is diluted in water. Aspect 21: Use in accordance with Aspect 20, wherein the dilution ratio of the formulation in water is 1:1, 1:2, 1:3, 1:4, 1:5, 1:6, 1:7, 1:8, 1:9, 1:10, 1:15, 1:20, 1:25, 1:30, 1:35, 1:40, 1:45, 1:50, 1:55, 1:60, 1:65, 1:70, 1:75, 1:80, 1:85, 1:90, 1:95, 1:100, 1:150, 1:200, 1:250, 1:300, 1:350, 1:400, 1:450, 1:500, 1:600, 1:700, 1:800, 1:900 or 1:1000. Aspect 22: Use in accordance with aspects 20 or 21, wherein the amount of the Formula I compound is from 0.1 percent to 20 percent, from 0.2 percent to 19 percent, from 0.3 percent to 18 percent, from 0.4 percent to 17 percent, from 0.5 percent to 16 percent, from 0.6 percent to 15 percent, from 0.7 percent to 14 percent, from 0.8 percent to 13 percent, from 0.9 percent to 12 percent, from 1 percent to 11 percent, from 1.1 percent to 10 percent, from 1.2 percent to 9 percent, from 1.3 percent to 8 percent, from 1.4 percent to 7 percent, from 1.5 percent to 6 percent percent, from 1.6 percent to 5 percent, from 1.7 percent to 4 percent or from 1.8 percent to 3 percent by weight of the diluted formulation. Aspect 23: Use in accordance with Aspect 1 to Aspect 22, wherein the formulation is applied to crops or agricultural plants by coating, spraying, soaking or irrigation. Aspect 24: Use in accordance with Aspect 23, wherein the formulation is applied to crops or agricultural plants by spraying. Aspect 25: Use in accordance with Aspect 1 to Aspect 24, wherein the formulation is applied to agricultural crops or plants 1, 2, 3, 4, 5 or 6 times within a 24-hour period. Aspect 26: Use in accordance with Aspect 1 to Aspect 25, wherein the formulation is applied to crops or agricultural plants with a frequency of every day, every second day, every fifth day, every week, every two weeks, or every month. Aspect 27: Use in accordance with Aspect 25 and 26, where the formulation is applied to crops or agricultural plants once every five days. Aspect 28: Use in accordance with Aspect 1 to Aspect 27, wherein the formulation is applied to agricultural crops or plants for at least 65 days, at least 60 days, at least 55 days, at least 50 days, at least 45 days or at least 40 days, or at least 35 days, or at least 30 days, or at least 25 days, or at least 20 days. Aspect 29: Use in accordance with Aspect 28, wherein the formulation is applied to crops or agricultural plants for at least 40 days. Aspect 30: Use of a Formula I compound to repel or reduce infestation of hemipteran insects, Formula 1 Where R represents hydrogen or C1-C5 alkyl, and represents a single or double bond, and where hemipteran insects are insects that feed on sap. Aspect 31: Use according to Aspect 30, wherein the compound of Formula I is anatabine, S-(-)anatabine, R-(+)anatabine, a mixture of S-(-)anatabine and R-(+)anatabine, or a racemate of S-(-)anatabine and R-(+)anatabine. Aspect 32: Use according to Aspects 30 or 31, wherein the hemipteran insects are whiteflies. Aspect 33: A method for repelling hemipteran insects, wherein the method comprises: a. prepare a concentrated formulation comprising a compound of Formula I, preferably anatabine; Formula 1 where R represents hydrogen or C1-C5 alkyl, and represents a single or double bond b. dilute the formulation in water at a predetermined dilution ratio or concentration; c. Apply the diluted formulation to crops or agricultural plants, preferably by spraying. Aspect 34: The method according to Aspect 33, wherein the hemipteran insects are whiteflies. For the purposes of this description and the appended claims, except where otherwise indicated, all numbers expressing quantities, figures, percentages, ratios, etc., are to be understood as modified in all cases by the term "approximately". Furthermore, all intervals include the maximum and minimum points described and include any intermediate intervals therewith, which may or may not be specifically enumerated in this description. In this context, therefore, a number A is understood to be A ± 5 percent of A. Within this context, a number A may be considered to include numerical values that are within the general standard error for the measurement of the property that modifies the number A.The number A, in some cases as used in the appended claims, may deviate by the percentages listed above, provided that the amount by which A deviates does not materially affect the basic and novel feature(s) of the claimed invention. Furthermore, all intervals include the maximum and minimum points described and include any intermediate intervals therein, which may or may not be specifically listed herein.
Claims
1. Use of a formulation for repelling or reducing infestation by hemipteran insects, wherein the formulation comprises a compound of Formula I, where R represents hydrogen or C1-C5 alkyl, and represents a single or double bond, and wherein the hemipteran insects are sap-feeding insects.
2. Use according to claim 1, wherein the hemipteran insects are whiteflies.
3. Use according to any preceding claim for repelling or reducing infestation by hemipteran insects on crops or agricultural plants.
4. Use according to claim 3, wherein the crops or agricultural plants are vulnerable to whitefly infestation.
5. Use according to claims 3 or 4, wherein the crops or agricultural plants are selected from tobacco plants, cereals, legumes, oilseed plants, Cucurbitaceae plants, fiber plants, vegetables, fruits, flowers, and ornamentals. 6.The use according to claims 3 to 5, wherein the crops or agricultural plants are tobacco plants.
7. The use according to claims 3 to 5, wherein the crops or agricultural plants are grown in a greenhouse.
8. The use according to any preceding claim, wherein the compound of Formula I is selected from anatabine, S-(-)anatabine, R-(+)anatabine, a mixture of S-(-)anatabine and R-(+)anatabine, or a racemate of S-(-)anatabine and R-(+)anatabine.
9. The use according to any preceding claim, wherein the formulation comprises a concentrate of the compound of Formula I. 10.Use according to any preceding claim, wherein the formulation comprises the compound of Formula I in an amount of at least 99 percent, at least 95 percent, at least 90 percent, at least 85 percent, at least 80 percent, at least 75 percent, at least 70 percent, at least 65 percent, at least 60 percent, at least 55 percent, at least 50 percent, at least 45 percent, at least 40 percent, at least 35 percent, at least 30 percent, at least 25 percent, at least 20 percent, at least 15 percent, at least 10 percent, at least 5 percent, at least 2.5 percent, or at least 1 percent by weight of the formulation.
11. Use according to any preceding claim, wherein the formulation is diluted in water. 12.The use according to claim 11, wherein the amount of the compound of Formula I is from 0.1 percent to 20 percent, from 0.2 percent to 19 percent, from 0.3 percent to 18 percent, from 0.4 percent to 17 percent, from 0.5 percent to 16 percent, from 0.6 percent to 15 percent, from 0.7 percent to 14 percent, from 0.8 percent to 13 percent, from 0.9 percent to 12 percent, from 1 percent to 11 percent, from 1.1 percent to 10 percent, from 1.2 percent to 9 percent, from 1.3 percent to 8 percent, from 1.4 percent to 7 percent, from 1.5 percent to 6 percent, from 1.6 percent 100 to 5 percent, 1.7 percent to 4 percent, or 1.8 percent to 3 percent by weight of the diluted formulation.
13. Use according to any preceding claim, wherein the formulation is applied to crops or agricultural plants by coating, spraying, soaking, or irrigation. 14.A method for repelling hemipteran insects, wherein the method comprises: a. preparing a concentrated formulation comprising a compound of Formula I, preferably anatabine; Formula I wherein R represents hydrogen or C1-C5 alkyl, and represents a single or double bond; b. diluting the formulation in water to a predetermined dilution ratio or concentration; c. applying the diluted formulation to crops or agricultural plants, preferably by spraying.