Classifications

• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
  • A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
  • A01N43/32—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms six-membered rings
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
  • C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
  • C07D327/06—Six-membered rings
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
  • C07D339/08—Six-membered rings

Definitions

• the present invention is concerned with a method of controlling pests such as arthropods, e.g. insects and acarine pests, helminths, e.g. nematodes, and molluscs e.g. slugs by contacting the pests with novel pesticides.
• pests such as arthropods, e.g. insects and acarine pests, helminths, e.g. nematodes, and molluscs e.g. slugs.
• novel pesticides used for controlling the pests and processes for making such pesticides.
• European Patent Applications 294228 and 294229 disclose inter alia that 5-substituted dithianes with a substituted phenyl moiety or a C 2 - 16 hydrocarbyl group at the 2-position have pesticidal activity.
• European Patent Application 102062 discloses inter alia that 5-disubstituted amino dithianes having a hydrocarbon or heterocyclic group at the 2-position have pesticidal activity.
• the present invention provides a method for controlling pests which comprises contacting the pest with a pesticidally effective amount of a compound of the formula (I):
• R 2a and R 2b are the same or different and each is selected from cyano, nitro, methyl optionally substituted by halo,a group S(O) q R 7 where q is 0, 1 or 2 and R 7 is methyl or ethyl, or a group COR 8 where R 8 is hydrogen, hydroxy, C 1-4 alkoxy, C 1-4 alkyl optionally substituted by fluoro or a group NR 9 R 10 wherein R 9 and R 10 are independently selected from hydrogen, methyl or ethyl; R 4a and R 4b , R 6a and R 6b are independently selected from hydrogen, methyl, cyano or trifluoromethyl, R 5a is a primary, secondary or tertiary C 2-5 alkyl group optionally substituted by halo or C 1-4 alkoxy, or a C 3-4
• halo is meant fluoro, chloro, bromo or iodo.
• hetero atom oxygen, sulphur (optionally present in an oxidised form) or nitrogen substituted by hydrogen or C 1-4 alkyl.
• Y is oxygen or sulphur.
• R 2a and R 2b are the same or different and each is selected from methyl, ethyl, cyano or trifluoromethyl.
• R 2a is methyl.
• R 4b is methyl or cyano.
• R 4a , R 4b , R 6a and R 6b are each selected from hydrogen, or methyl, and preferably they are all hydrogen.
• R 5a is a secondary or tertiary C 2-5 alkyl group optionally substituted by fluoro or a cyclopropyl group.
• R 5a is tertiary butyl or 2,2,2-trifluoro-1-methylethyl.
• R 5b is hydrogen, methyl or ethyl, preferably R 5b is hydrogen.
• a compound of the formula (I) wherein R 2a , R 4a , R 4b , R 5b , R 6a , R 6b , m and n are as hereinbefore defined and R 2b is cyano, nitro, a group S(O)q R 7 , a group COR 8 wherein q, R 7 and R 8 are as hereinbefore defined, or a C 1-3 alkyl group substituted by halo.
• the compounds of the formula (I) may exist in a number of stereoisomeric forms.
• the present invention encompasses both individual conformational and stereoisomers and mixtures thereof.
• the present invention also encompasses compounds of the formula (I), containing radioisotopes particularly those in which or one to three hydrogen atoms are replaced by tritium or one or more carbon atoms are replaced by 14 C.
• Preferred compounds of the invention include:
• the present invention also provides for the preparation of the compounds of the formula (I) by methods derived from those known in the art for the preparation of analogous compounds.
• the compounds may be prepared
• X is SH and Y 1 is SH or OH with a suitable aldehyde or ketone of the or a reactive derivative thereof, wherein the R substituents at the 2, 4, 5 and 6 positions are as hereinbefore defined and, if required, thereafter oxidizing one or two ring sulphur atoms.
• the reaction is suitably carried out in the presence of a catalyst or of a dehydrating agent in a non-polar solvent at a non-extreme temperature.
• Suitable catalysts include a dimethyl formamide/dimethyl sulphate catalyst and catalysts such as sulphonic acids or perfluorinated resins thereof or Lewis acids such as boron trifluoride etherate, or stannic chloride or concentrated formic acid which also serves as the reaction medium.
• Suitable solvents include hydrocarbons such as benzene, toluene or xylene or chlorinated hydrocarbons such as dichloromethane.
• the reaction is normally performed between 0 and 200 and conveniently between 20 and 120 Suitable reactive derivatives of aldehydes and ketones include acetals and ketals.
• the compounds of the formula (II) may be prepared from the corresponding diols wherein X and Y are hydroxy.
• the dithiols may be prepared via the sulphonate derivatives (i.e., compounds of the formula (II) wherein X and Y are groups OSO FaceR wherein R 11 is C 1-4 alkyl or para-tolyl) and the hydroxythiols may be prepared via precursors of the formula (II) in which X is halo, particularly bromo, and Y is a protected hydroxy group, for example an acetoxy group.
• This precursor is then reacted with an appropriate reagent for replacing the halo atom with sulphur, for example potassium thiocyanate or thioacetate, followed by alkaline hydrolysis.
• an appropriate reagent for replacing the halo atom with sulphur for example potassium thiocyanate or thioacetate
• alkaline hydrolysis for example potassium thiocyanate or thioacetate
• the preparation of the diols and their conversion to the corresponding dithiols can be carried out by methods known in the art.
• Suitable alkylating agents include alkyl halides, for example methyl iodide.
• the reaction is suitably carried out in the presence of a strong base such as butyllithium in an inert solvent, for example an ether such as tetrahydrofuran, at a non-extreme temperature, conveniently between -100 and 50oC and suitably between -70o and 30°C.
• the compounds of the formula (III) are suitably prepared by conversion of the corresponding compound containing an aldehyde function instead of a nitrile group. This conversion may be carried out by the reaction of the aldehyde with a suitable reagent such as O, N-bis (trifluoroacetyl)-hydroxylamine.
• This aldehyde is prepared in turn from the 2-unsubstituted dithiane or oxathiane by reaction with a formylating agent, such as dimethylformamide, in the presence of a strong base, for example butyllithium.
• a compound of the formula (IV) by reaction of a compound of the formula (IV) :
• R 11 is C 1-4 alkyl and R 12 is methyl optionally substituted b y halo, with a trialkylsilylcyanide in the presence of an acid catalyst.
• the alkyl groups in the trialkylsilylcyanide reagent contain 1 to 4 carbon atoms and are preferably methyl groups.
• the acid catalyst is a Lewis acid such as boron trifluoride etherate.
• the reaction is carried out in an inert solvent, such as a halogenated hydrocarbon, e.g. dichloromethane, at a non extreme temperature, for example between -50 and 80oC, and conveniently between 0 and 30oC.
• the compounds of the formula (IV) may be prepared by the reaction of a compound of the formula (II) with the appropriate orthoester of the formula (V):
• R 12 and R 13 are as hereinbefore defined.
• This reaction is conveniently carried out in the presence of an acid catalyst such as para toluene sulphonic acid, at an elevated temperature, i.e. between
• the compounds of the formula (I) wherein one or more of m and n is other than 0 may be prepared by oxidation of the corresponding compound of a lower oxidation state.
• the reaction is usually carried out in an inert solvent such as acetonitrile or a halogenated hydrocarbon such as chloroform at a non-extreme temperature, for example between 0 and 100 C and preferably between 20 and 30oC.
• Suitable oxidising agents include peracids such as metachloro- perbenzoic acid.
• the oxidation is conveniently carried out in the presence of a buffer such as anhydrous sodium acetate.
• Compounds where m is 2 and n is 0 may be prepared from compounds of the formula (I) where m is 0 or 1, using potassium permanganate in a ketone, for example, acetone, at a non-extreme temperature for example -30oC to 100 C and conveniently between -10o and 30oC.
• the compounds of formula (I) may be used to control pests such as arthropods, e.g. insect and acarine pests, helminths, e.g. nematodes and molluscs, e.g. slugs.
• arthropods e.g. insect and acarine pests
• helminths e.g. nematodes
• molluscs e.g. slugs.
• the present invention provides a method for the control of arthropods, helminths and/or molluscs which comprises administering to the arthropod, helminth and/or mollusc or to their environment an effective amount of a compound of the formula (I).
• the present invention also provides a method for the control of arthropod, helminth and/or mollusc infestations of animals (including humans) and/or of plants (including trees) and/or stored products which comprises administering an effective amount of a compound of the formula (I).
• the present invention further provides for the compounds of the formula (I) for use in human and veterinary medicine, in public health control and in agriculture for the control of arthropod, helminth and/or mollusc pests.
• control is meant the amelioration of present or future deleterious effects of pests and includes killing adults, larvae and eggs, the inhibition of reproduction, the repellency and/or knockdown of pests, and any other influence on behaviour.
• Compounds of formula (I) are of particular value in the protection of field, forage, plantation, glasshouse, orchard and vineyard crops, of ornamentals and of plantation and forest trees, for example, cereals (such as maize, wheat, rice, millet, oats, barley, sorghum), cotton, tobacco, vegetables and salads (such as beans, cole crops, cucurbits, lettuce, onions, tomatoes and peppers), field crops (such as potato, sugar beet, ground nuts, soyabean, oil seed rape), sugar cane, grassland and forage crops (such as lucerne), plantations (such as of tea, coffee, cocoa, banana, oil palm, coconut, rubber, spices), orchards and groves (such as of stone and pip fruit, citrus fruits, kiwifruit, avocado, mango, olives and walnuts), vineyards, ornamental plants, flowers and shrubs under glass and in gardens and parks, forest trees (both deciduous and evergreen) in forests, plantations and nurseries and plants
• Compounds of formula (I) are of value in the control of public health pests, for example cockroaches and ants.
• Compounds of formula I are also of value in the control of arthropods, helminths or molluscs which are injurious to, or spread or act as vectors of diseases in man and domestic animals, for example those hereinbefore mentioned, and more especially in the control of ticks, mites, lice, fleas, midges biting, nuisance and myiasis flies, mosquitos, hemiptrean bugs and snails.
• the compounds of Formula (I) may be used for such purposes by application of the compounds themselves or in diluted form in known fashion as a dip, spray, fog, lacquer, foam, dust, powder, aqueous suspension, paste, gel, cream, shampoo, grease, combustible solid, vapourising mat, combustible coil, bait, dietary supplement, wettable powder, granule, aerosol, emulsifiable concentrate, oil suspension, oil solution, pressure-pack, impregnated article, microcapsule, pour on formulation or other standard formulations well known to those skilled in the art.
• Sprays may be applied by hand or by means of a spray race or arch or by vehicle or aircraft mounted apparatus.
• the animal, soil, plant or other surface being treated may be saturated with the spray by means of high volume application or superficially coated with the spray by means of light or ultra low volume application.
• Dip concentrates are not applied per se. but diluted with water and the animals immersed in a dipping bath containing the dip wash.
• Aqueous suspensions may be applied in the same manner as sprays or dips.
• Dusts may be distributed by means of a powder applicator or, in the case of animals, incorporated in perforated bags attached to trees or rubbing bars.
• Pastes, shampoos and greases may be applied manually or distributed over the surface of an inert material, such as that against which animals rub and transfer the material to their skins.
• Pour-on formulations are dispensed as a unit of liquid of small volume on to the backs of animals such that all or most of the liquid is retained on the animals.
• Compounds of Formula (I) may be prepared either as formulations ready for use on the animals, plants or surface or as formulations requiring dilution prior to application, but both types of formulation comprise a compound of Formula (I) in intimate admixture with one or more carriers or diluents.
• the carriers may be liquid, solid or gaseous or comprise mixtures of such substances, and the compound of Formula (I) may be present in a concentration of from 0.025 to 99% w/v depending upon whether the formulation requires further dilution.
• Dusts, powders and granules and other solid formulations comprise the compound of formula (I) in intimate admixture with a powdered solid inert carrier for example suitable clays, kaolin, bentonite, attapulgite, adsorbent carbon black, talc, mica, silica, chalk, gypsum, tricalcium phosphate, powdered cork, magnesium silicate, vegetable carriers, starch and diatomaceous earths.
• a powdered solid inert carrier for example suitable clays, kaolin, bentonite, attapulgite, adsorbent carbon black, talc, mica, silica, chalk, gypsum, tricalcium phosphate, powdered cork, magnesium silicate, vegetable carriers, starch and diatomaceous earths.
• Such solid formulations are generally prepared by impregnating the solid diluents with solutions of the compound of formula (I) in volatile solvents, evaporating the solvents and, if desired, grinding the products so as to obtain powders and, if desired, granulating, compacting or encapsulating the products.
• Sprays of a compound of Formula (I) may comprise a solution in an organic solvent (e.g. those listed below) or an emulsion in water (dip wash or spray wash) prepared in the field from an emulsifiable concentrate (otherwise known as a water miscible oil) which may also be used for dipping purposes.
• the concentrate preferably comprises a mixture of the active ingredient, with or without an organic solvent and one or more emulsifiers.
• Solvents may be present within wide limits but preferably in an amount of from 0 to 99.5% w/v of the composition and may be selected from kerosene, ketones, alcohols, xylene, aromatic naphtha, water, mineral oil, aromatic and aliphatic esters, and other solvents known in the formulating art.
• the concentration of emulsifiers may be varied within wide limits but is preferably in the range of 5 to 25% w/v and the emulsifiers are conveniently non-ionic surface active agents including polyoxyalkylene esters of alkyl phenols and polyoxyethylene derivatives of hexitol anhydrides and anionic surface active agents including Na lauryl sulphate, fatty alcohol ether sulphates, Na and Ca salts of alkyl aryl sulphonates and alkyl sulphosuccinates, soaps, lecithins, hydrolysed glues, etc.
• non-ionic surface active agents including polyoxyalkylene esters of alkyl phenols and polyoxyethylene derivatives of hexitol anhydrides and anionic surface active agents including Na lauryl sulphate, fatty alcohol ether sulphates, Na and Ca salts of alkyl aryl sulphonates and alkyl sulphosuccinates, soaps, lecithin
• Wettable powders comprise an inert solid carrier, one or more surface active agents, and optionally stabilisers and/or anti-oxidants.
• Emulsifiable concentrates comprise emulsifying agents, and often an organic solvent, such as kerosene, ketones, alcohols, xylenes, aromatic naphtha, and other solvents known in the art.
• organic solvent such as kerosene, ketones, alcohols, xylenes, aromatic naphtha, and other solvents known in the art.
• Wettable powders and emulsifiable concentrates will normally contain from 0.5 to 99.5% by weight of the active ingredient, and are diluted, for example with water, before use.
• Lacquers comprise a solution of the active ingredient in an organic solvent, together with a resin, and optionally a plasticiser.
• Dip washes may be prepared not only from emulsifiable concentrates but also from wettable powders, soap based dips and aqueous suspensions comprising a compound of Formula (I) in intimate admixture with a dispersing agent and one or more surface active agents.
• Aqueous suspensions of a compound of Formula (I) may comprise a suspension in water together with suspending, stabilizing or other agents.
• the suspensions or solutions may be applied per se or in a diluted form in known fashion.
• Greases may be prepared from vegetable oils, synthetic esters of fatty acids or wool fat together with an inert base such as soft paraffin. A compound of Formula (I) is preferably distributed uniformly through the mixture in solution or suspension. Greases may also be made from emulsifiable concentrates by diluting them with an ointment base.
• Pastes and shampoos are also semi-solid preparations in which a compound of Formula (I) may be present as an uniform dispersion in a suitable base such as soft or liquid paraffin or made on a non-greasy basis with glycerin, mucilage or a suitable soap.
• a suitable base such as soft or liquid paraffin or made on a non-greasy basis with glycerin, mucilage or a suitable soap.
• shampoos and pastes are usually applied without further dilution they should contain the appropriate percentage of the compound of Formula (I) required for treatment.
• Aerosol sprays may be prepared as a simple solution of the active ingredient in the aerosol propellant and co-solvent such as halogenated alkanes, propane, butane, dimethyl ether and the solvents referred to above, respectively.
• Pour-on formulations may be made as a solution or suspension of a compound of Formula (I) in a liquid medium.
• An avian or mammal host may also be protected against infestation of acarine ectoparasites by means of carrying a suitably-moulded, shaped plastics article impregnated with a compound of Formula (I).
• Such articles include impregnated collars, tags, bands, sheets and strips suitably attached to appropriate parts of the body.
• the plastics material is a polyvinyl chloride (PVC).
• the concentration of the compound of formula (I) to be applied to an animal, premises, other substrates or outdoor areas will vary according to the compound chosen, the interval between treatments, the nature of the formulation and the likely infestation, but in general 0.001 to 20.0% w/v and preferably 0.01 to 10% of the compound should be present in the applied formulation.
• the amount of the compound deposited will vary according to the compound chosen, the method of application, area of application, concentration of the compound in the applied formulation, factor by which the formulation is diluted and the nature of the formulation.
• Undiluted formulations such as pour-on formulations in general will be applied at a concentration in the range from 0.1 to 20.0% w/w and preferably 0.1 to 10%.
• the amount of compound to be applied to stored products in general will lie in the range of from 0.1 to 20ppm.
• Space sprays may be applied to give an average initial concentration of 0.001 to 1 mg of compound of formula (I) per cubic metre of treated space.
• Compounds of formula (I) are of use in the protection and treatment of plant species, in which case an effective insecticidal, acaricidal, nematocidal or molluscicidal amount of the active ingredient is applied.
• the application rate will vary according to the compound chosen, the nature of the formulation, the mode of application, the plant species, the planting density and likely infestation and other like factors but in general, a suitable use rate for agricultural crops is in the range 0.001 to 3kg/Ha and preferably between 0.01 and lkg/Ha.
• Typical formulations for agricultural use contain between 0.0001% and 50% of a compound of formula (I) and conveniently between 0.1 and 15% by weight of a compound of the formula (I). Dusts, greases, pastes and aerosol formulations are usually applied in a random fashion as described above and concentrations of 0.001 to 20% w/v of a compound of Formula (I) in the applied formulation may be used.
• the compounds of formula (I) have been found to have activity against the common housefly (Musca domestica). In addition, certain compounds of formula (I) have activity against other arthropod pests including Myzus persicae, Tetranychus urticae, Plutella xylostella, Culex spp. Tribolium castaneum, Sitophilus granarius, Periplaneta americana and Blattella germanica, The compounds of formula (I) are thus useful in the control of arthropods e.g. insects and acarines in any environment where these constitute pests, e.g. in agriculture, in animal husbandry, in public health control and in domestic situations.
• arthropods e.g. insects and acarines in any environment where these constitute pests, e.g. in agriculture, in animal husbandry, in public health control and in domestic situations.
• Insect pests include members of the orders Coleoptera (e.g. Anobium,Ceutorhynchus,Rhynchophorus, Cosmopolites, Lissorhoptrus, Melipethes, Hypothenemus, Hylesinus, Acalymma, Lema, Psylliodes, Leptinotarsa, Gonocephalum, Agriotes, Dermolepida, Heteronychus, Phaedon, Tribolium, Sitophilus Diabrotica, Anthonomus or Anthrenus spp.), Lepidoptera (e.g. Anobium,Ceutorhynchus,Rhynchophorus, Cosmopolites, Lissorhoptrus, Melipethes, Hypothenemus, Hylesinus, Acalymma, Lema, Psylliodes, Leptinotarsa, Gonocephalum, Agriotes, Dermolepida, Heteronych
• Ephestia Mamestra, Earias, Pectinophora, Ostrinia, Trichoplusia, Pieris, Laphygma, Agrotis, Amathes, Wiseana. Tryporvza, Diatraea, Sporganothis, Cydia, Archios, Plutella, Chilo, Heliothis, Spodoptera or Tineola spp,), Diptera (e.g.
• Musca Musca, Aedes, Anopheles, Culex, Glossina, Simulium, Stomoxys, Haematobia, Tabanus, Hydrotaea, Lucilia, Chrysomia, Callitroga, Dermatobia, Gasterophilus, Hvpoderma, Hylemyia, Atherigona, Chlorops, Phvtomvza, Ceratitis, Liriomyza and Melophagus spp.), Phthiraptera (Malophaga e.g. Damalina spp. and Anoplura e.g. Linognathus and Haematopinus spp.), Hemiptera (e.g.
• Aphis Bemisia,Phorodon, Aeneolamia, Empoasca, Parkinsiella, Pyrilla, Aonidiella, Coccus, Pseudococcus, Helopeltis, Lygus, Dysdercus, Oxycarenus, Nezara, Aleurodes, Triatoma, Rhodnius, Psylla, Myzus, Megoura, Phylloxera, Adelves, Niloparvata, Nephrotettix or Cimex spp,), Orthoptera (e.g. Locusta, Gryllus, Schistocerca or Acheta spp,), Dictyoptera (e.g.
• Blattella, Periplaneta or Blatta spp. Hymenoptera (e.g. Athalia. Cephus, Atta Lasius. Solenopsis or Monomorium spp.), Isoptera (e.g. Odontotermes and Reticulitermes spp.), Siphonaptera (e.g. Ctenocephalides or Pulex spp.), Thysanura (e.g. Lepisma spp.), Dermaptera (e.g. Forficula spp.), Psocoptera (e.g. Peripsocus spp.) and Thysanoptera (e.g. Thrips tabaci),.
• Isoptera e.g. Odontotermes and Reticulitermes spp.
• Siphonaptera e.g. Ctenocephalides or Pulex spp.
• Thysanura e.g. Lepisma spp.
• Dermaptera
• Acarine pests include ticks, e.g. members of the genera Boophilus,Ornithodorus, Rhipicephalus, Amblyomma, Hyalomma. Ixodes, Haemaphysalis, Dermacentor and Anocentor, and mites and manges such as Acarus, Tetranychus, Psoroptes, Notoednes, Sarcoptes. Psorergates, Chorioptes, Eutrombicula. Demodex, Panonychus, Bryobia and Eriophyes spp.
• Nematodes which attack plants and trees of importance to agriculture, forestry, horticulture, either directly or by spreading bacterial, viral, mycoplasma or fungal diseases of the plants include root-knot nematodes such as Meloidogyne spp. (e.g. M. incognita) : cyst nematodes such as Globodera spp. (e.g. G. rostochiensis): Heterodera spp. (e.g. H. avenae); Radopholus spp. (e.g. R. similis); lesion nematodes such as Pratylenchus spp. (e.g. P.
• root-knot nematodes such as Meloidogyne spp. (e.g. M. incognita) : cyst nematodes such as Globodera spp. (e.g. G. rostochiensis): Heterodera s
• Belonolaimus spp. e.g. B. gracilis
• Tylenchulus spp. e.g. T. semipenetrans
• Rotylenchulus spp. e.g.R. reniformis
• Rotylenchus spp. e.g. R. robustus
• Helicotylenchus spp. e.g. H. multicinctus
• Hemicvc1iophora spp. e.g. H. gracilis
• Criconemoides spp. e.g. C. similis
• Trichodorus spp. e.g.
• T primitivus dagger nematodes such as Xiphinema spp. (e.g. X. diversicaudatum), Longidorus spp (e.g. L. elongatus): Hoplolaimus spp. (e.g. H. coronatus); Aphelenchoides spp. (e.g. A. ritzema-bosi. A. besseyi): stem and bulb eelworms such as Ditylenchus spp. (e.g. D. dipsaci).
• Xiphinema spp. e.g. X. diversicaudatum
• Longidorus spp e.g. L. elongatus
• Hoplolaimus spp. e.g. H. coronatus
• Aphelenchoides spp. e.g. A. ritzema-bosi. A.
• Mollusc pests which attack plants and trees of importance to agriculture, foresty and horticulture include slugs such as Deroceras spp. (e.g. P. reticulatum - the grey field slug); the Arion group; Milax spp; land snails such as Helix spp. and aquatic snails such as Planorbis spp.
• Mollusc pests which act as vectors of diseases in man and domestic animals include Bulinus spp., Physopsis spp., Planorbis spp. and Oricomelania spp.
• Compounds of the invention may be combined with one or more other pesticidally active ingredients (for example pyrethroids, carbamates lipid amides and organophosphates) and/or with attractants, repellents, bacteriocides, fungicides, anthelmintics and the like.
• the activity of compounds of the invention may be enhanced by the addition of a synergist or potentiator, for example: one of the oxidase inhibitor class of synergists, such as piperonyl butoxide, propyl 2-propynylphenyl- phosphonate; a second compound of the invention; or a pyrethroid pesticidal compound.
• a synergist or potentiator for example: one of the oxidase inhibitor class of synergists, such as piperonyl butoxide, propyl 2-propynylphenyl- phosphonate; a second compound of the invention; or a pyrethroid pest
• Stabilisers for preventing any chemical degradation which may occur with the compounds of the invention include, for example, antioxidants (such as tocopherols, butylhydroxyanisole and butylhydroxytoluene) and scavengers (such as epichlorhydrin) and organic or inorganic bases e.g. trialkylamines such as triethylamine which can act as basic stabilisers and as scavengers.
• antioxidants such as tocopherols, butylhydroxyanisole and butylhydroxytoluene
• scavengers such as epichlorhydrin
• organic or inorganic bases e.g. trialkylamines such as triethylamine which can act as basic stabilisers and as scavengers.
• 5-t-Butyl-2-methyl-1,3-dithiane (4.7g) was obtained as a pale yellow oil which solidified on cooling. ii) Using the methods described in Example 1 stages (i) and (ii), 5-t-butyl-2-methyl-1,3-dithiane was converted to 5(e)-t-butyl- 2(a)-methyl-1,3-dithiane-2(e)-carbonitrile.
• 3,3-Dimethyl-2-mercaptomethylbutan-1-ol was obtained as a pale yellow oil (2.8g) and was used without further purification.
• v) A mixture of 3,3-dimethyl-2-mercaptomethylbutan-1-ol (1.66g), triethyl orthoacetate (1.82g) and p-toluenesulphonic acid (catalytic quantity) was heated under a stream of nitrogen until no further ethanol was evolved. The resultant brown oil was purified by chromatography on alumina, eluting with 4% dichloro- methane (saturated with ammonia) in hexane.
• 5-t-Butyl-2-(a)-ethoxy-2(e)-methyl-1,3-oxathiane (1.0g) was obtained as a pale yellow oil.
• Trimethylsilyl cyanide (0.37g) was added to a solution of 5-t-butyl-2(a)-ethoxy-2(e)-methyl-1,3-oxathiane (0.78g) in dichloromethane (10ml) at 0oC under nitrogen, followed by boron trifluoride etherate (0.025g), in a dropwise manner, and the solution allowed to warm to room temperature overnight.
• the yellow solution was diluted with ether, washed with sodium bicarbonate solution, brine, dried over sodium sulphate and evaporated in vacuo.
• Potassium permanganate (0.36g) was added to a stirred mixture of 5(e)-t-butyl-2(e)-methyl-1,3-dithiane-2(a)-carbonitrile 1(e)-oxide (0.35g) and magnesium sulphate (Ig) in acetone (15ml). The resulting mixture was maintained at room temperature for 4 hours and then filtered through Celite. The colourless filtrate was evaporated in vacuo to leave 5 (e) - t-butyl-2 (e) -methyl- 1 , 3-dithiane- 2 (a) -carbonitrile 1 , 1-dioxide as a white solid (0. 33g) .
• Alkyl aryl sulphonate* 1. 00 Napthalene sulphonic acid* 3. 00 Diatomaceous earth 46. 00
• Aerosol pressure pack
• Aerosol pressure pack
• Antioxidant could be any of the following individually or combined
• Vitamin C (ascrobic acid)
• the activity of the compounds of the invention was demonstrated by dissolving the compounds in acetone (5%) and then diluting in water: "Synperonic” (94.5%: 0.5%) to give an aqueous emulsion. This was used to treat the following insects.
• Filter paper and food were sprayed with a solution of the compound. Subsequently, the filter paper was infested with 10 second instar larvae. Mortality was assessed after 48 hours.

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• 1990
  • 1990-12-19 GB GB909027571A patent/GB9027571D0/en active Pending
• 1991
  • 1991-12-18 EP EP92901389A patent/EP0565550A1/en not_active Withdrawn
  • 1991-12-18 HU HU9301793A patent/HUT65130A/hu unknown
  • 1991-12-18 BR BR919107171A patent/BR9107171A/pt not_active Application Discontinuation
  • 1991-12-18 AU AU91041/91A patent/AU648626B2/en not_active Ceased
  • 1991-12-18 WO PCT/GB1991/002268 patent/WO1992011254A1/en not_active Application Discontinuation
  • 1991-12-18 CZ CS931143A patent/CZ114393A3/cs unknown
  • 1991-12-18 JP JP4501455A patent/JPH06503825A/ja active Pending
  • 1991-12-18 CA CA002098704A patent/CA2098704A1/en not_active Abandoned
  • 1991-12-18 KR KR1019930701861A patent/KR930703289A/ko not_active Application Discontinuation
• 1993
  • 1993-06-18 FI FI932846A patent/FI932846A0/fi not_active Application Discontinuation
  • 1993-06-18 NO NO93932258A patent/NO932258L/no unknown

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