WO2001007047A2 - Lutte contre l'infestation d'animaux aquatiques par des ectoparasites de crustaces - Google Patents

Lutte contre l'infestation d'animaux aquatiques par des ectoparasites de crustaces Download PDF

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WO2001007047A2
WO2001007047A2 PCT/IB2000/001002 IB0001002W WO0107047A2 WO 2001007047 A2 WO2001007047 A2 WO 2001007047A2 IB 0001002 W IB0001002 W IB 0001002W WO 0107047 A2 WO0107047 A2 WO 0107047A2
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compound
species
juvenile hormone
group
fish
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PCT/IB2000/001002
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English (en)
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WO2001007047A3 (fr
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Yngve STENSTRØM
Christian Syvertsen
Lars SKATTEBØL
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Bioparken As
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Priority to CA002378409A priority Critical patent/CA2378409A1/fr
Priority to EP00944146A priority patent/EP1204413A2/fr
Priority to AU58379/00A priority patent/AU5837900A/en
Publication of WO2001007047A2 publication Critical patent/WO2001007047A2/fr
Publication of WO2001007047A3 publication Critical patent/WO2001007047A3/fr
Priority to NO20020360A priority patent/NO20020360L/no

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N49/00—Biocides, pest repellants or attractants, or plant growth regulators, containing compounds containing the group, wherein m+n>=1, both X together may also mean —Y— or a direct carbon-to-carbon bond, and the carbon atoms marked with an asterisk are not part of any ring system other than that which may be formed by the atoms X, the carbon atoms in square brackets being part of any acyclic or cyclic structure, or the group, wherein A means a carbon atom or Y, n>=0, and not more than one of these carbon atoms being a member of the same ring system, e.g. juvenile insect hormones or mimics thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P15/00—Biocides for specific purposes not provided for in groups A01P1/00 - A01P13/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • A61K31/23—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin of acids having a carboxyl group bound to a chain of seven or more carbon atoms
    • A61K31/231—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin of acids having a carboxyl group bound to a chain of seven or more carbon atoms having one or two double bonds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/255—Esters, e.g. nitroglycerine, selenocyanates of sulfoxy acids or sulfur analogues thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/336—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having three-membered rings, e.g. oxirane, fumagillin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
    • A61K31/381—Heterocyclic compounds having sulfur as a ring hetero atom having five-membered rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • A61K31/5375—1,4-Oxazines, e.g. morpholine

Definitions

  • the present invention relates in its broadest aspect to the production of aquatic animals such as fish.
  • novel and improved means of controlling parasitic crustacean infestations of fish, including farmed fish, using juvenile hormone analogue compounds are provided.
  • Ectoparasitic infestations constitute considerable problems in the fish farming industry as well as in wild fish. However, the problems are particularly serious in farmed fish in both fresh water and sea water environments. Damages due to ectoparasitic infestations of fish result in considerable losses and increased workloads for fish farmers.
  • parasitic species of crustacean ectoparasites also generally referred to as sea lice, are particularly harmful.
  • infestation with sea lice in- eluding Lepeophtheirus salmonis and Caligus elongatus is considered to be one of the most important disease problems in farming of salmonids, especially in Atlantic salmon (Salmo sala ⁇ and rainbow trout (Oncorhynchus mykiss).
  • lower classification ratings of slaughtered fish and reduced growth rate due to reduced feed intake contribute to the economic losses caused by sea lice.
  • the life cycle of Lepeophtheirus salmonis is direct, meaning that no intermediate host is required for the development of the adult lice.
  • the two nauplius stages of this species are pelagic.
  • It moults to the first chalimus stage which is attached to its host by a frontal filament projecting from the leading edge of the parasite's carapace. All four chalimus stages are attached to the host by this filament.
  • the frontal filament is normally lost, and the parasite may move around on the skin of the host.
  • sea lice could be the most important single cause leading to weakening of several wild salmon stocks.
  • the emigration of salmon smolt from river systems is often coincidental with rising sea water temperatures in the fjord and coastal areas, which leads to a massive attack of copepodites (sea lice larvae) on the smolt.
  • An attack of 40 or more sea lice on salmon smolt is fatal to fish weighing less than 25 grams, and in several regions premature return of post-smolt sea trout has been observed.
  • the decline in the stock of salmonids that have been documented in several salmon rivers over the past few years, could be related to the fact that the amount of sea lice in connection with fish farming has increased.
  • Substances that are effective against parasitic infestations via oral administration have also been tested in fish.
  • Substances such as the chitin synthesis inhibitors diflubenzuron and teflubenzuron are examples of substances, which, if administered orally, can be effective against parasitic diseases in fish.
  • wrasse (Labridae) has been used extensively to keep sea lice infestations under control.
  • Organophosphates and hydrogen peroxide are only effective against the pre-adult and adult stages of sea lice (the last 3 stages of the total of 8 stages which exist on the skin of salmonids), while pyrethroids and ivermectin also have a more or less well-defined effect against the other 5 stages. None of these substances protect against new infestations af- ter the treatment has been completed. Hydrogen peroxide is corrosive, and must therefore be handled with great care. Transport of hydrogen peroxide requires certain precautionary measures, as it is defined as hazardous goods in great quantities. The organophosphates are toxic to humans and must therefore be treated with caution. The organophosphates can be absorbed through the skin and lead to poisoning. The therapeutic margin for organophosphates and hydrogen peroxide is small. Fish mortality has been reported on several occasions, due to overdosing of such drugs.
  • Pyrethroids have, in addition to their effect against pre-adult and adult lice, also an effect against the attached stages. They are not acutely toxic to the user, but is a drug group that is toxic to fish, especially small fish. Overdosing and increased mortality of the target fish is thus possible.
  • Diflubenzuron and tefiubenzuron act by inhibiting the synthesis of chitin which is an im- portant component of the cuticle of insects and crustaceans. At each moulting or ectdysis, a new synthesis of chitin is required for development. If this synthesis is inhibited, the development of the insect or crustacean will be halted, and the animal under development will die. In principle, chitin synthesis inhibitors will be effective against all organisms containing chitin. Fish and mammals do not contain chitin and will therefore not be affected by substances within this drug group. This is reflected in very low toxicity for fish and mammals, including humans.
  • Diflubenzuron and tefiubenzuron are administered to the fish via the feed, absorbed and distributed to skin and mucus, where the concentration will be high enough to inhibit the development of the parasite.
  • the disadvantages of diflubenzuron and tefiubenzuron include that these substances have no effect against adult stages of the ectoparasites which do not actively synthesise chitin. Neither do they have any effect beyond the period of treatment, as attacks by new parasites may occur within days of completing the treatment. This is due to the fact that the substances are eliminated relatively fast so that the concentration hereof rapidly ends up below therapeutically active levels in skin and mucus. The treatment must therefore be repeated if there is a continu- ous risk of parasite infection from the surroundings which, under normal circumstances, is often the case.
  • Ivermectin impairs the transfer of neural impulses in insects and crustaceans. This leads to paralysis and death. Mammals and fish are also affected by ivermectin. However, the same transfer mechanisms that are affected in insects, are only found in the brain of fish and mammals. Mammals have an advanced blood-brain barrier which prevents toxic effect from lower concentrations. The blood-brain barrier in fish is less developed and this causes a substantial transition to the brain of ivermectin in treated fish, and toxic symp- toms are found at relatively low concentrations. Ivermectin, however, is effective for treatment of ectoparasites in fish provided that precautions with the dosing are taken.
  • Ivermectin is often dosed 1 or 2 times a week to control sea lice infestation in salmonids. This means that the substance must be added on a continuous basis to maintain therapeutic effect and keep the fish reasonably free of lice. Ivermectin is eliminated at a slow rate which means that the effect of the treatment is maintained for 2 to 3 weeks after the treatment has been completed. This also means, however, that the treatment involves a long withdrawal period before the fish can be slaughtered and consumed. Up till now, ivermectin has not been approved for use in fish in any country.
  • insects include moulting hormones (MH), also referred to as ecdysones, and juvenile hormones (JH) that are terpenoid compounds.
  • MH moulting hormones
  • JH juvenile hormones
  • the juvenile hor- mones that are released from the corpora allata in the insect's head play vital roles in growth, development and reproduction of insects. If insects are treated with an excess of the juvenile hormone at an early stage in their development, they remain at a juvenile stage or develop into a sterile adult insect.
  • JH analogues also referred to herein as juvenile hormone-like compounds, juvenoids or JH mimics
  • examples of such compounds include epofenonane, triprene, methoprene, hydroprene, kinoprene, phenoxycarb and those compounds disclosed in US 4,061 ,757.
  • typical uses of JH analogues include control of mosquitoes, mites, ants, aphids, cockroaches and fleas.
  • the present invention pertains in a first aspect to the use of a compound having juvenile hormone activity, in the manufacturing of a medicament for controlling crustacean infestation of aquatic animals including fish such as wild and farmed fish of the Salmonidae family.
  • novel juvenile hormone analogue compounds se- lected from the group consisting of
  • R 1 is alkyl, branched alkyl including alkenyl or alkadienyl, optionally substituted isoprenoid or alkoxy substituted alkyl
  • R 2 is hydrogen or alkyl
  • X is oxygen, sulfur, methyl- ene, carbinol or carbonyl
  • Y is nitrogen or methine and Z is nitrogen, methine or nitrogen oxide
  • R 1 is 2,2-dimethylcyclopropyl, 2,2-dihalo-3,3-dimethylcyclopropyl, 2-methyl-1- propenyl or 3-methyl-1 ,2-butadienyl
  • R 2 is hydrogen or methoxy
  • R 3 is alkyl, alkenyl, ace- tyl, formyl or carbomethoxy
  • R 4 is hydrogen or R 3 and R 4 together is methylenedioxy and
  • X is oxygen or sulfur
  • R is 2-methylbutyl, 2,2-dimethylcyclopropyl or 2,2-d ⁇ halo-3,3-dimethylcyclopropyl and R 2 is methyl, ethyl or isopropyl,
  • X oxygen or sulfur and Ar is a heteroaromatic group
  • 57 2-(3',7'-Dimethyloctylsulfanyl)thiophene; 58: 1 ,4-Dioctylpiperidine; F-1 : 3-[2'-(4"-Phenoxyphenoxy)ethoxy]pyridine; F-4: 2-[2'-(4"-Phenoxyphenoxy)ethoxy]pyridine; and F-5: 3-(4'-Phenoxybenzyloxy)pyridine.
  • the invention provides a method of controlling crustacean infestation of an aquatic animal, the method comprising administering to said animal or to the aquatic environment of the animal an effective amount of a juvenile hormone analogue compound including any of the above novel compounds.
  • compositions for controlling crustacean infestation of an aquatic animal comprising a juvenile hormone analogue compound and at least one pharmaceutically acceptable carrier, and an aquatic animal feed composition comprising a juvenile hormone analogue compound.
  • a major objective of the present invention is to provide improved means for controlling crustacean ectoparasitic infestations in aquatic animals such as fish.
  • the invention is based on the finding that a range of compounds having juvenile hormone activity generally referred to as juvenile hormone analogues (JHAs), which are known to have insect controlling activities including insecticidal activity, have a strong inhibiting effect on the metamorphosis of parasitic crustacean species resulting in a high mortality of these parasites not only in vitro but also in vivo, i.e. when the parasites are attached to the host animal, rendering such compounds potentially useful in the control of such ectoparasitic infestations in live fish.
  • JHAs juvenile hormone analogues
  • the term "juvenile hormone analogue” indicates a synthetic compound that is structurally and/or functionally related to the naturally occurring juvenile hormones I, II and III, terpenoid substances that are found in insects where they regulate the development from the larval stage to the imago stage of the insects. Due to this juvenile hor- mone effect, JHAs are currently used as insect controlling agents (see e.g. US 4,002,615 and 4,061 ,757). Juvenile hormone analogues are also referred to as juvenoids or juvenile hormone mimics.
  • the use according to the invention is particularly interesting for manufacturing medicaments for control of crustacean infestation in fish species having their natural habitat in cold, temperate or warm water environments.
  • the medicament of the invention can be used therapeutically and/or prophylactically for controlling infestations in both wild and farmed fish including ornamental fish, occurring in freshwater, sea water or brackish water.
  • Fish that can be treated with JHAs include any fish that can be infestated by ecto- parasitic crustaceans such as wild and farmed fish belonging to the Salmonidae family including, but not limited to Salmo salar, Salmo trutta, Salmo clarkii, Oncorhynchus gor- buscha, Oncorhynchus keta, Oncorhynchus nekra, Oncorhynchus kisutch, Oncorhynchus tshawytscha, Oncorhynchus mason, Oncorhynchus mossambicus, Oncorhynchus mykiss and Salvelinus species.
  • ecto- parasitic crustaceans such as wild and farmed fish belonging to the Salmonidae family including, but not limited to Salmo salar, Salmo trutta, Salmo clarkii, Oncorhynchus gor- buscha, Oncorhynchus keta, Oncorhynch
  • JHAs include carps, whitefish, roach, rudd, chub, sole, plaice, Japanese yellowtail, sea bass, sea bream, grey mullet, po pano, gilthread seabream, Tilapia spp., Cichlidae spp., cod, halibut, wolf fish, flounder, aju and eel including Japanese eel.
  • Presently preferred target fish for the present invention include Atlantic salmon, Pacific salmon and trout.
  • JHA compounds effectively control infestations by crustacean species generally referred to as sea lice such as Lepeophtheirus species.
  • sea lice such as Lepeophtheirus species.
  • JHAs will be effective against other ectoparasitic crustacean species infestating aquatic animals. Such species are i.a.
  • important target species of crustaceans include Lepeophtheirus salmonis, Caligus elongatus and Aniiocra physodes L, crustaceans of a species selected from the group consisting of an Aniiocra species, a Chymothoa species, a Lironeca species, a Meinertia species, an Olencira species and a Bopyrus species and crustaceans of the Iso- poda class including Aniiocra physodes, Chymothoa exigua, Lironeca californica, Lironeca convexa, Lironeca ovalis, Lironeca vulgaris, Meinertia oestroides, Meinertia parallela and Olencira praegustator.
  • any compound having juvenile hormone activity includes any compound having juvenile hormone activity, includ- ing a juvenile hormone analogue compound, that is effective with respect to retarding or inhibiting any stage of the development of crustaceans from the first larval stage to the pre-adult stage and/or which has a biological effect on any stage of the crustaceans including the adult stage is encompassed.
  • a compound according to the invention that is capable of retarding or inhibiting at least one stage shift from the nauplius I stage through further nauplius stages, copepodite stages, chalimus stages, the pre-adult stage to the adult stage.
  • Such compounds include juvenile hormone mimics such as epofe- nonane, phenoxycarb, hydroprene, kinoprene, methoprene, pyriproxyfen and triprene, juvenile hormones I, II and III, and the compounds disclosed in US 4,002,615 and 4,061 ,757. It should be understood that chitin synthesis inhibitors are not included in the above definition of compounds having juvenile hormone activity.
  • kits for evaluating compounds for juvenile hormone activity are also encompassed within the meaning of compounds having "juvenile hormone activity”
  • compounds having "juvenile hormone activity” are compounds which prove to be positive when tested in a standard test system for evaluating compounds for juvenile hormone activity.
  • Such standard tests wherein Teni- brio molitor typically is applied as test organism, are well known in the art (se e.g. Slama et al., Insect Hormones and Bioanalogues, Springer-Verlag, New York 1974, p. 93).
  • Juvenile hormone activity may be determined using newly-molted (4-8 hours) Tenib o molitor pupae.
  • the compounds to be evaluated are formulated to contain 10 ⁇ g in 1 ml of solution. Acetone is the preferred solvent and is used in both topical and vapor tests.
  • Topical application is with a micro applicator (Isco model M) fitted with a tuberculin syringe and a 27 gauge needle.
  • One ⁇ l of the desired solution is administered/pupa on the venter of the last three abdominal segments.
  • Vapor action is determined by applying the candidate compound to the lower 1/3 of a 1 pint freezer type jar and then inverting the jar into a 1/2 pint container, containing 5 pupae.
  • a dosage of 1 ⁇ l of the desired solution per pupa (5 ⁇ l/jar) is used. All pupae are held until the following molt to determine juvenile hormone activity, which is indicated by the presence of immature characters; e.g. i) retention of gin traps, ii) retention of gin traps and urogomphi, iii) retention of gin traps and urogomphi plus retention of pupal cuticle around area of treatment, and iv) 2nd pupae - retention of all pupal characters. If a perfect adult is obtained after molting, the compound has no juvenile hormone activity.
  • Famesyl methyl ether is used as the standard for both topical and vapor tests.
  • particularly interesting compounds having juvenile hormone activ- ity include:
  • R 1 is alkyl, branched alkyl including alkenyl or alkadienyl, optionally substituted iso- prenoid or alkoxy substituted alkyl
  • R 2 is hydrogen or alkyl
  • X is oxygen, sulfur, methylene, carbinol or carbonyl
  • Y is nitrogen or methinine and Z is nitrogen, methine or nitrogen oxide
  • R 1 is 2,2-dimethylcyclopropyl, 2,2-dihalo-3,3-dimethylcyclopropyl, 2-methyl-1- propenyl or 3-methyl-1 ,2-butadienyl
  • R 2 is hydrogen or methoxy
  • R 3 is alkyl, alkenyl, ace- tyl, formyl or carbomethoxy
  • R 4 is hydrogen or R 3 and R 4 together is methylenedioxy and
  • X is oxygen or sulfur
  • R is 2-methylbutyl, 2,2-dimethylcyclopropyl or 2,2-dihalo-3,3-dimethylcyclopropyl and R 2 is methyl, ethyl or isopropyl, and (iv) a compound of the general formula IV
  • JHA juvenile hormone analogue compounds
  • R-2 (3'R)-5-(3 ⁇ 7'-Dimethyloctyloxy)-2-methylpyridine;
  • F-2 3-(7'-Ethoxy-3',7'-dimethyloctyloxy)pyridine
  • F-4 2-[2'-(4"-Phenoxyphenoxy)ethoxy]pyridine
  • F-5 3-(4'-Phenoxybenzyloxy)pyridine; 25 methoprene; and hydroprene.
  • the fish or any other aquatic animal species can be treated orally, e.g. via their feed, or by bath treatment, e.g. in a medicinal bath where the fish are kept for a period of time
  • the active compounds are administered in medicament formulations which are adjusted to the applications.
  • Formulations for oral administration include e.g. powders, granulates, solutions, emulsifiable concentrates or suspension concentrates which are mixed homogeneously as feed additives with the feed, or powders, granulates, emulsifiable concen- trates or suspension concentrates which are administered in the form of pills, the outer coat of which can consist e.g. of fish feed compositions which cover the active substance completely.
  • the active substance may be applied onto the surface of feed particles such as pellets or granules, e.g. incorporated in a lipid component such as a fish oil.
  • Useful medicament formulations for bath application or for treating the biotope of the fish include powders, granulates, solutions, emulsions, micro-emulsions, suspensions, tablets or the active substance itself. The end-user may use these formulations in dilute or undi- lute form.
  • the active compound in any of these formulations may be used in pure form, as a solid active substance e.g. in a specific particle size, or together with at least one of the adjuvants that are conventionally used in formulation technology, such as extenders, typically solvents or solid carriers, or surface active compounds.
  • the formulations are prepared in a manner known per se, typically by mixing, granulating and/or compacting the active compound with solid or liquid carriers, where appropriate, with the addition of further auxiliary substances such as emulsifying or dispersing agents, solubilisers, colorants, antioxidants and/or preservatives.
  • the active substance which is suspended or dissolved in oily or fatty matrices, is washed out on administration.
  • the release can be controlled by the choice of adjuvants, concentration of the active substance and form.
  • Coprimates or melts of hard fats comprising the active sub- stance are also suitable for use.
  • compositions of this invention are generally prepared by contacting the active substance with liquid and/or solid formulation assistants by stepwise mixing and/or grinding such that an optimal development of the antiparasitic activity of the formulation is achieved that conforms with the application.
  • Formulation assistants can e.g. be solid carriers, solvents and, where appropriate, surface active substances which are non-toxic for marine fauna and flora.
  • the bath application of the medicament compositions of the invention to the parasites to be controlled can e.g. be carried out such that the compositions are placed in the cage in the form of solutions, emulsions, micro-emulsions, suspensions, powders or tablets, where they are dissolved or dispersed by the movement of the fish and the flow of the water. Concentrated compositions can also be diluted with large volumes of water before applied to the cages.
  • micro-emulsions can advantageously be applied for bath application of the medicament compositions when using juvenile hormone analogues which are not water-soluble or have a low water-solubility.
  • juvenile hormone analogues which are not water-soluble or have a low water-solubility.
  • the micro-emulsion comprises solvents, surfactants and stabilisers in addition to the juvenile hormone analogues.
  • no water should be pres- ent in the micro-emulsion.
  • solvents which can be applied in a micro-emulsion include acetone, mono- hydric, dihydric or polyhydric alcohol (including ethanol, polyethylene glycol, propylene glycol), glycerine, mineral oil, vegetable oils or oils of animal origin, fatty acid esters, di- methyl sulphoxid (DMSO), dioxan, tetrahydrofuran (THF), 2-pyrrolidon, N-methyl-2- pyrrolidon.
  • acetone mono- hydric, dihydric or polyhydric alcohol (including ethanol, polyethylene glycol, propylene glycol), glycerine, mineral oil, vegetable oils or oils of animal origin, fatty acid esters, di- methyl sulphoxid (DMSO), dioxan, tetrahydrofuran (THF), 2-pyrrolidon, N-methyl-2- pyrrolidon.
  • DMSO di- methyl sulphoxid
  • THF tetrahydrofuran
  • 2-pyrrolidon
  • surfactants include acetylated mono-and diglycerides with fatty acids, polyacrylic copolymers, beeswax, lecithin, fatty acids, guar gum, xanthan gum, tragacanth gum, PEG linked with fatty acids or sugars, hydrogenated and etoxylated castor oil, cellulose derivatives, compounds consisting of fatty acids esterified to sugars, N-octyl-2-pyrrolidon, N-dodecyl-2-pyrrolidon, EO/PO blockpolymers and dodecylbenzene sulfonate salts.
  • stabilisers include antioxidants, pH regulating compounds such as citric acid, and complexing agents.
  • the micro-emulsion comprises: i) juvenile hormone analogues in an amount which is in the range of 0.1-10 wt% including the range of 0.5-5 wt%; ii) sol- vents in the range of 20-30 wt% including the range of 22-28 wt% such as in the range of 25-28 wt%; iii) surfactants in the range of 50-80 wt% including the range of 55-75 wt% such as in the range of 60 to 70 wt%; and iv) stabilisers in the range of 0.1-5 wt% including the range of 0.5-5 wt% such as in the range of 1 to 2 wt%.
  • a specific composition of a micro-emulsion is given in the below examples.
  • the invention relates to novel juvenile hormone analogue compounds of the general formula I, the general formula II, the general formula III or of the general formula IV and the compounds 55-58, F-1, F-4 and F-5 as defined above, including a compound of the general formula II having saturated side chains to the aromatic ring, for use as a medicament for treating or preventing crustacean infestations in an aquatic animal.
  • any of the above juvenile hormone analogues including epofenonane, phenoxycarb, hydroprene, kinoprene, methoprene and triprene and the above compounds of the general formula I, the general formula II, the general formula ill or of the general formula IV as also defined above can be used as the antiparasitically active compound.
  • the active compound is administered by any of the above routes using the compound as such or in the form of a composition that is adjusted to the selected manner of administration, including compositions for bath treatment or addition to the biotope of animals or fish, compositions for oral administration, optionally via the feed, or injectable compositions.
  • the amount of active substance in the administration form can vary depending i.a. on the dosage form, the target parasite, the age and condition of the fish to be treated.
  • the amount of the active juve- nile hormone analogue compound in the environment of the aquatic animal depends on the manner and duration of treatment and also on the age and condition of the fish to be treated. Effective dosages of the active substance in the water is generally in the range of 1 ppb to 1 ppm such as in the range of 10 ppb to 500 ppb including the range of 100 to 5 300 ppb.
  • the compound is added the aquatic environment in the form of a micro-emulsion
  • a pharmaceutical composition for controlling crustacean infestation of an aquatic animal comprising a juve- 0 nile hormone analogue compound and at least one pharmaceutically acceptable carrier.
  • suitable carriers include, but are not limited to, solid carriers such as e.g. kaolin, talcum, bentonite, sodium chloride, calcium phosphate, carbohydrates, cellulose, cotton seed meal, polyethylene glycol ether and, if necessary, binders such as gelatine, soluble cellulose derivatives or surface active substances such as ionic or anionic dispers- 5 ing agents.
  • such a composition can e.g. be in the form of a powder, a granulate, a suspension, an emulsion, a micro-emulsion and a solution or it can for certain purposes be in the form of an injectable composition.
  • the composition of the invention may further comprise a component selected from the group consisting of a solvent, a wetting agent, an emulsifying agent, a bulking agent and a dispersing agent.
  • Suitable solvents include aromatic hydrocarbons, alkylated naphtalenes, or tetrahydronaphtalenes, aliphatic or cycloaliphatic hydrocarbons such as paraffins or cyclohexane, alcohols such as ethanol, propanol or butanol, glycois and their esters and 5 ethers, ketones such as acetone, strongly polar solvents such as N-methyl-2-pyrrolidone, dimethyl sulfoxide, water, as well as vegetable oils and oils of animal origin such as e.g. fish oil.
  • suitable surface active compounds are nonionic, 0 cationic and/or anionic surfactants having good emulsifying, dispersing and/or wetting properties.
  • composition of the invention can comprise two or more juvenile hormone analogue compounds or it can comprise at least one further anti-parasitically 5 active compound of any of the conventionally used types of antiparasitic substances in- eluding formaldehyde, hydrogen peroxide, a cholinesterase inhibitor such as e.g. metri- fonate or dichlorvos, an organophosphorus compound, a carbamate compound, a chitin inhibiting compound, an avermectin compound and/or a pyrethroid compound.
  • an aquatic animal feed composition comprising a juvenile hormone analogue compound as defined above, in an amount that will provide an antiparasitically active amount of the JH analogue compound in the fish.
  • the active compound can be in- corporated in the feed in any of the above manners.
  • the active compound can be mixed directly with the feed ingredient as such or it can be added in the form of a more or less concentrated feed additive composition.
  • such an additive composition can consist of 1-10 wt% of active compound, 49-90 wt% of a protein carrier such as soy bean protein, 0-50 wt% of ground calcium powder, 0-2 wt% of an alcohol, hydroxypropyl cellu- lose and water ad 100 wt%.
  • Suitable forms of "medicated" feed comprising the JH analogue compound include granulated feed, pelleted feed and feed in the form of an emulsion or micro-emulsion.
  • the amount of the juvenile hormone analogue in feed compositions of the invention is typically in the range of 0.001 to 5 % wt% such as 0.01 to 3 wt% including 0.1 to 1 wt%.
  • the feed composition of the invention can comprise two or more juvenile hormone analogue compounds or it can comprise at least one further anti-parasitically active compound of any of the conventionally used types of antiparasitic substances including formaldehyde, hydrogen peroxide, a cholinesterase inhibitor such as e.g. metrifonate or dichlorvos, an organophosphorus compound, a carbamate compound, a chitin inhibiting compound, an avermectin compound and/or a pyrethroid compound.
  • Fig. 1 shows the percentage of copepodite larvae relative to the number of nauplius larvae exposed to compound 6 as defined herein [5-(3',7'-Dimethylocta-2',6'-dienyloxy)-2- methylpyridine] at concentrations of 0.01 ppm, 0.05 ppm, 0.3 pp and 1.0 ppm, respec- tively for 1 , 5 and 24 hours, respectively (Example 3); Fig.
  • Fig. 3 shows the percentage of copepodite larvae relative to the number of nauplius larvae exposed to compound 59 as defined herein [3-(3',7'-Dimethyloctyloxy)pyridine;] at concentrations of 0.3 ppm and 1.0 ppm for 1 , 5 and 24 hours, respectively (Example 3);
  • Fig. 4 shows the ratio between number of copepodites in groups of Lepeophtheirus salmonis larvae exposed compounds 6, 7 or 59 for 1 , 5 and 24 hours, respectively at concentrations of 0.01 ppm, 0.05 ppm, 0.3 ppm and 1.0 ppm, respectively (Example 3). Data for these exposure periods were combined for each concentration and the controls for each compound were combined. A ratio of 1 indicates that the same number of copepodites were developed in the exposed groups and the control groups; and
  • Fig. 5 summarises the results of the experiments in Example 4 where Lepeophtheirus salmonis nauplius stage larvae were exposed for 24 hours to 1.0 ppm of compounds 4 [2- Methyl-5-octyloxypyridine], 2 [5-(3',7'-Dimethyloctyloxy)-2-methylpyridine, 34 [(3,7- Dimethyloctyloxy)benzene], 17 [5-(3',7'-Dimethyloctyloxy)benzo[1 ,3]dioxole] 60 [3-(3',7'- Dimethyloctylsulfanyl)pyridine] or 61 [(3',7'-Dimethylocta-2',6'-dienyloxy)benzene].
  • F-2 3-(7'-Ethoxy-3',7'-dimethyloctyloxy)pyridine
  • F-4 2-[2'-(4"-Phenoxyphenoxy)ethoxy]pyridine
  • AD hydroprene
  • JH juvenile hormone
  • the JH analogue compounds 51 , 1 and 50 were tested at a concentration of 0.7 ppm to determine their effect on the development from nauplius larvae to copepodites as compared to a control group not exposed to JH analogue. After 14 days of exposure the number of copepodites were calculated. Most of the nauplius larvae in the control group de- veloped into copepodites. Larvae exposed to the compounds 51 and 50 showed results that were similar to the control. However, no copepodites were present in the group exposed to the compound 1 , and only dead nauplius larvae were found.
  • JH analogue compounds 6, 7 and 59 The effect of JH analogue compounds 6, 7 and 59 on the development of Lepeophtheirus salmonis from nauplius stage to copepodite stage
  • Example 2 The apparently most effective compounds from Example 2 were selected for further investigation.
  • the effect of the compounds 6, 7 and 59 on the development from nauplius larvae to copepodites were tested at concentrations of 0.01 ppm, 0.05 ppm, 0.3 ppm and 1.0 ppm, respectively at the exposure periods of 1 , 5 and 24 hours, respectively.
  • the number of nauplius and copepodite larvae were counted after 3-7 days.
  • the experi- ments were run in triplicate at each concentration and each exposure period. Additionally, control groups exposed to equivalent amount of acetone used as solvent for the test compounds were included.
  • the compounds 4, 2, 34, 17, 60 and 61 were tested using the protocol as in Example 1 using exposure at 1.0 ppm for 24 hours. The results of this experiment are shown in Fig. 5. All of the tested compounds except compound 61 completely inhibited the development from the nauplius to the copepodite stage. The compound 60 were tested further at 1.0 ppm using an exposure period of only 1 hour. Under these conditions, the compound had a good effect in that only 7% of the larvae exposed developed into the copepodite stage.
  • Example 2 The experiments were conducted essentially as in Example 2. 10-50 newly hatched nau- plius I larvae were placed in trays containing 50 ml of sea water (temperature 16-19°C, salinity 2.2%) to which the compound to be tested was added at 1.0 ppm and the exposure time was 24 hours following which the larvae were separated from the water and transferred to fresh sea water. After 3-5 days, the number of nauplii and copepodites were counted. Acetone was used as solvent for the compounds and the same volume of ace- tone was added to trays with control larvae. All experiments were carried out in triplicate or quadruplicate.
  • the compounds F-1, F-2, F-3, F4 and F-5 were tested for their effect on nauplius stage larvae at a concentration of 1.0 ppm. The number of surviving and dead nauplii in the trays were counted immediately after exposure.
  • the compounds B, C, F, I and J had the best larvicidal effect on the sea lice larvae. None of the larvae reached the copepodite stage during the screening period. In the groups B and C, the distribution of dead larvae were equal between nauplius stages 1 and 2. For the groups I, J and K, nauplius 1 larvae dominated among the dead larvae, whereas stage 2 nauplii dominated among the dead larvae in group F.
  • the commercial juvenile hormone analogue compound methoprene (AC) was tested.
  • test fish were distributed into tanks of 500 I (45 fish per tank).
  • Running sea water that was adjusted in respect of oxygen (at least 70% saturation in outlet water), salinity (34 promille) and temperature (11.5°C) was supplied to the tanks.
  • the photoperiod was set at 18 hours of light and 6 hours of dark throughout the test period.
  • the total average number of all sea lice stages in controls is 98 per fish while in the group treated with JH analogue 59 this number is reduced to 61.
  • salmon in neighbouring cages were heavily infested with sea lice, migration of adult and pre-adult lice to the experimental groups occurred.
  • the significant reduction in chalimus stages in the group treated with JH analogue 59 shows that development of copepodite through the four chalimus stages is inhibited by the treatment.
  • the juvenile hormone analogues methoprene (AC) and hydroprene (AD) were tested.
  • the test fish were distributed into tanks of 500 I with 45 fish per tank.
  • the photoperiod was set at 18 hours of light and 6 hours of dark throughout the test period.
  • Table 10.1 is given an example of a base micro-emulsion concentrate for bath treatment of fish with a juvenile hormone analogue.
  • the micro-emulsion is prepared in a tank kept at a constant temperature of 30°C, by adding the juvenile hormone analogue to the solvents (N-metyl-2-pyrrolidon and N-octyl- 2-pyrrolidon) while stirring, and subsequently adding the remaining components (polyok- syl 35 castor oil, tetrapropylene benzenesulfonate Ca-salt and citric acid) to the mixture.
  • the solvents N-metyl-2-pyrrolidon and N-octyl- 2-pyrrolidon
  • the juvenile hormone analogue In bath treatment of fish, the juvenile hormone analogue is typically applied at concentration of 0.1 to 1 ppm.
  • 0.2 litre of micro-emulsion concentrate (stock solution) containing 50g juvenile hormone analogue per kg is added to the 100m 3 of water.
  • This micro-emulsion concentrate comprising the juvenile hormone analogue can advantageously be diluted in a volume of water, e.g. 10 litres, before it is added to the aquatic environment wherein the fish to be treated is kept. A clear solution is seen when the micro-emulsion comprising the juvenile hormone analogue is added to the water.

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Abstract

L'invention concerne l'utilisation de composés analogues d'hormone juvénile (juvénoïdes, analogues d'hormone juvénile), afin de lutter contre l'infestation d'un poisson par des ectoparasites de crustacés, telle que l'infestation par des poux du poisson, en particulier des infestations par le lepeophtheirus salmonis et le caligus elongatus chez les poissons sauvages ou d'élevage de la famille des salmonidae, notamment le saumon et la truite d'Atlantique. Ces composés sont, de préférence, administrés via l'alimentation ou une médication de traitement par bain.
PCT/IB2000/001002 1999-07-23 2000-07-20 Lutte contre l'infestation d'animaux aquatiques par des ectoparasites de crustaces WO2001007047A2 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
CA002378409A CA2378409A1 (fr) 1999-07-23 2000-07-20 Lutte contre l'infestation d'animaux aquatiques par des ectoparasites de crustaces
EP00944146A EP1204413A2 (fr) 1999-07-23 2000-07-20 Lutte contre l'infestation d'animaux aquatiques par des ectoparasites de crustaces
AU58379/00A AU5837900A (en) 1999-07-23 2000-07-20 Control of crustacean infestation of aquatic animals
NO20020360A NO20020360L (no) 1999-07-23 2002-01-23 Bekjempelse av lakselus

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DKPA199901054 1999-07-23
DKPA199901054 1999-07-23

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WO2001007047A3 WO2001007047A3 (fr) 2001-12-20

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EP (1) EP1204413A2 (fr)
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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001006853A2 (fr) * 1999-07-23 2001-02-01 Bioparken As Nouveaux analogues de l'hormone juvenile utilises comme agents anti-salissures
GB2371053A (en) * 2001-01-13 2002-07-17 David R Harper Microbiological control of sea lice
RU2480447C2 (ru) * 2006-03-23 2013-04-27 Пронова Биофарма Норге Ас Конъюгированные липидные производные
WO2016024168A1 (fr) * 2014-08-12 2016-02-18 Institut de Recherche en Semiochimie et Ethologie Appliquee Acide palmitoléique destiné à être utilisé pour inhiber la fixation de poux du poisson sur des poissons

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* Cited by examiner, † Cited by third party
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WO2001006853A2 (fr) * 1999-07-23 2001-02-01 Bioparken As Nouveaux analogues de l'hormone juvenile utilises comme agents anti-salissures
WO2001006853A3 (fr) * 1999-07-23 2001-12-20 Bioparken As Nouveaux analogues de l'hormone juvenile utilises comme agents anti-salissures
GB2371053A (en) * 2001-01-13 2002-07-17 David R Harper Microbiological control of sea lice
RU2480447C2 (ru) * 2006-03-23 2013-04-27 Пронова Биофарма Норге Ас Конъюгированные липидные производные
WO2016024168A1 (fr) * 2014-08-12 2016-02-18 Institut de Recherche en Semiochimie et Ethologie Appliquee Acide palmitoléique destiné à être utilisé pour inhiber la fixation de poux du poisson sur des poissons
CN106999460A (zh) * 2014-08-12 2017-08-01 信息化学和应用神经研究所 用于抑制海虱附着于鱼上的棕榈油酸
AU2015303009B2 (en) * 2014-08-12 2020-10-29 Institut de Recherche en Semiochimie et Ethologie Appliquee Palmitoleic acid for use in inhibiting the attachment of sea lice to fish
US11020364B2 (en) 2014-08-12 2021-06-01 Institut de Recherche en Semiochimie et Ethologie Appliquee Palmitoleic acid for use in inhibiting the attachment of sea lice to fish

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NO20020360D0 (no) 2002-01-23
EP1204413A2 (fr) 2002-05-15

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