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
  • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
  • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
• • 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
  • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
  • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
  • A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
• • 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
  • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
  • A61K31/42—Oxazoles
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P33/00—Antiparasitic agents
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P33/00—Antiparasitic agents
  • A61P33/10—Anthelmintics
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P33/00—Antiparasitic agents
  • A61P33/14—Ectoparasiticides, e.g. scabicides
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
  • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
  • C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
  • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
  • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
  • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings

Definitions

• the present invention relates to novel and inventive parasiticidal and pesticidal isoxazoline com ounds of formula (I):
• compositions comprising at least one compound of formula (I) in combination with a pharmaceutically acceptable or agriculturally acceptable carrier.
• the invention also relates to uses of the compounds and methods comprising the compounds for the treatment and prevention of parasitic infections or infestations and for controlling pests in crops, plants, plant propagation material and material derived from wood.
• ectoparasites such as insects
• endoparasites such as nematodes and other worms.
• domesticated animals such as cats and dogs, are often infested with one or more of the following ectoparasites:
• - fleas e.g. Ctenocephalides spp., such as Ctenocephalides felis and the like;
• ticks e.g. Rhipicephalus spp., Ixodes spp., Dermacentor spp., Amblyoma spp., and the like
• - mites e.g. Demodex spp., Sarcoptes spp., Otodectes spp., and the like
• - lice e.g. Trichodectes spp., Cheyletiella spp., Linognathus spp. and the like
• Trichodectes spp. Cheyletiella spp., Linognathus spp. and the like
• Fleas are a particular problem because not only do they adversely affect the health of the animal or human, but they also cause a great deal of psychological stress. Moreover, fleas may also transmit pathogenic agents to animals and humans, such as tapeworm (Dipylidium caninum).
• ticks are also harmful to the physical and psychological health of the animal or human.
• Major diseases which may be transmitted by ticks include borrelioses (Lyme disease caused by Borrelia burgdorferi), babesiosis (or piroplasmoses caused by Babesia spp.) and rickettsioses (e.g. Rocky Mountain spotted fever).
• Ticks also release toxins which cause inflammation or paralysis in the host. Occasionally, these toxins are fatal to the host.
• farm animals are also susceptible to parasite infestations.
• a parasite which is prevalent among cattle in some regions are ticks of the genus Rhipicephalus, especially those of the species microplus (cattle tick), decoloratus and annulatus. Ticks such as Rhipicephalus microplus (formerly Boophilus microplus) are difficult to control because they lay eggs in the pasture where farm animals graze.
• This species of ticks is considered a one-host tick and spends immature and adult stages on one animal before the female engorges and falls off the host to lay eggs in the environment. The life cycle of the tick is approximately three to four weeks.
• Rhipicephalus microplus may infest buffalo, horses, donkeys, goats, sheep, deer, pigs, and dogs.
• a heavy tick burden on animals can decrease production and damage hides as well as transmit diseases such as babesiosis ("cattle fever") and anaplasmosis.
• helminthiasis which is caused by of parasitic worms categorized as cestodes (tapeworm), nematodes (roundworm) and trematodes (flatworm or flukes).
• cestodes tapeworm
• nematodes roundworm
• trematodes flatworm or flukes
• parasites which occur in the gastrointestinal tract of animals and humans include Ancylostoma, Necator, Ascaris, Strongyloides, Trichinella, Capillaria, Toxocara, Toxascaris, Trichiris, Enterobius and parasites which are found in the blood or other tissues and organs such as filarial worms and the extra intestinal stages of Strogyloides, Toxocara and Trichinella.
• Various patent publications have described isoxazoline derivatives having pesticidal properties,
• compositions comprising these compounds and use of the compounds in the fields of agriculture and veterinary medicine.
• JP2010/235590 and JP2010/168367 have also described isoxazoline derivatives having pesticidal activity and compositions comprising these compounds.
• WO 2009/097992 describes arylpyrrolines with pesticidal activity
• WO 2008/128711 and WO 2010/043315 describes aryl pyrrolidines that are active against pests.
• WO 2009/1 12275 describes condensed ring aryl compounds with pesticidal activity.
• the present invention provides novel and inventive isoxazoline compounds of formula (I), (IA), (IB), (IC), (ID) and (IE) shown below that are biologically active against parasites that harm animals and against pests that damage crops, plants, plant propagation material and material derived from wood. Accordingly, the application provides parasiticidal and pesticidal compositions comprising the isoxazoline compounds in combination with a pharmaceutically acceptable carrier or an agriculturally acceptable carrier.
• the present invention also provides methods for the treatment or prevention of a parasitic infection or infestation in an animal and for controlling pests that harm plants, plant propagation material and material derived from wood, which comprise administering an effective amount of a compound of the invention to the animal or to the plants, or the soil in which the infected plant grows, or the wood-derived material, with a pesticidally effective amount of a compound of formula (I).
• a first object of the invention is to provide parasiticidal and pesticidal novel and inventive isoxazoline com ounds of formulae (I), (IA), (IB), (IC), (ID) and (IE):
• variables D 1 , D 2 , D 3 , D 4 , D 5 , R 1 , A 1 , A 3 , B 1 , B 2 , B 3 , R 2 , R 3 , R 3' , R 4 , R 4' , R 5 , R 5 , R 6 , R 6' , Y, Z, L, a and b are described herein.
• compositions for the treatment or prevention of parasitic infections and infestations in animals comprising a parasiticidally effective amount of at least one compound of formula (I), (IA), (IB), (IC), (ID) or (IE), or a veterinarily acceptable salt thereof, in combination with a pharmaceutically acceptable carrier.
• the compositions may be formulated for oral, subcutaneous, parenteral, and topical administration including spot-on and pour-on administration.
• Another object of the invention is to provide pesticidal compositions comprising at least one compound of formula (I), (IA), (IB), (IC), (ID) or (IE), or a pesticidally acceptable salt thereof, for combating pests that are harmful to plants, plant propagation material or material derived from wood in combination with a pesticidally effective carrier.
• Another object of the invention is to provide veterinary compositions comprising at least one compound of formula (I), (IA), (IB), (IC), (ID) or (IE), or a veterinarily acceptable salt thereof, for combating parasites comprising a parasiticidally effective amount of the compounds of the invention, or veterinarily acceptable salts thereof, in combination with one more other active agent and a veterinarily acceptable carrier or diluent.
• Another object of the invention is to provide agricultural compositions comprising at least one compound of formula (I), (IA), (IB), (IC), (ID) or (IE), or an agriculturally acceptable salt thereof, for combating pests comprising a pesticidally effective amount of the compounds of the invention, or agriculturally acceptable salts thereof, in combination with one more other active agent and an agriculturally acceptable carrier or diluent.
• Another object of the invention is to provide plant propagation material (e.g. seed), comprising at least one compound of formula (I), (IA), (IB), (IC), (ID) or (IE) or agriculturally acceptable salts thereof, and plant propagation material that has been treated with at least one compound of formula (I), (IA), (IB), (IC), (ID) or (IE), or an agriculturally acceptable salt thereof, or a composition comprising the compound.
• plant propagation material e.g. seed
• plant propagation material comprising at least one compound of formula (I), (IA), (IB), (IC), (ID) or (IE) or agriculturally acceptable salts thereof
• plant propagation material e.g. seed
• Another object of this invention is to provide methods of treatment and prevention of parasitic infections or infestations in or on an animal, which comprise treating the infected animal with a parasiticidally effective amount of a compound of formula (I), (IA), (IB), (IC), (ID) or (IE), or a veterinarily acceptable salt thereof.
• Another object of this invention is to provide methods for combating pests on crops, plants, plant propagation material or material derived from wood, which comprises treating the infected plant, or the soil in which the infected plant grows, or the wood-derived material with a pesticidally effective amount of a compound of formula (I), (IA), (IB), (IC), (ID) or (IE), or a pesticidally acceptable salt thereof.
• Another object of the invention is to provide methods for combating or controlling pests at a locus (excluding an animal), comprising administering a pesticidally or parasiticidally effective amount of a compound of formula (I), (IA), (IB), (IC), (ID) or (IE), or veterinarily or agriculturally acceptable salts thereof, to the locus.
• Another object of the invention is to provide use of a compound of formula (I), (IA),
• Still another object of the invention is use of a compound of formula (I), (IA), (IB), (IC), (ID) or (IE), or a veterinarily acceptable salt thereof, in the preparation of a medicament for the treatment or prevention of a parasitic infestation or infection in or on an animal.
• the invention provides a compound of formula
• Still another object of this invention is to provide processes for the preparation of isoxazoline compounds of formula (I), (I), (IA), (IB), (IC), (ID) or (IE).
• the present invention does not intend to encompass within the scope of the invention any previously disclosed compound, product, process of making the product or method of using the product, which meets the written description and enablement requirements of the USPTO (35 U.S.C. 1 12, first paragraph) or the EPO (Article 83 of the EPC), such that the applicant(s) reserve the right and hereby disclose a disclaimer of any previously described product, method of making the product or process of using the product.
• novel and inventive isoxazoline compounds of formula (I), (IA), (IB), (IC), (ID) and (IE) of the invention have been found to have superior activity against pests, including parasites that cause harm to animals, and pests that damage plants, plant propagation material and material containing wood or derived from wood. Accordingly, the compounds of the invention have been found useful for preventing and treating a parasitic infestation/infection in an animal and for controlling and eradicating pests that damage plants, plant propagation material and material derived from wood.
• the present invention provides novel and inventive isoxazoline compounds and compositions comprising the compounds. Furthermore, the invention provides methods for preventing and/or treating a parasitic infestation or infection in an animal, and the use of the compounds for treating a parasitic infestation or infection in an animal or the use of the compounds in the manufacture of a medicament for treating a parasitic infestation or infection in an animal.
• the invention provides novel and inventive isoxazoline compounds that are exceptionally potent against ectoparasites that harm animals.
• the compounds described herein may be used to treat and prevent parasitic infestations in animals.
• the present invention provides uses of the compounds for controlling and eradicating pests that cause damage to plants, plant propagation material and material derived from wood. In still another embodiment, the present invention provides uses of the isoxazoline compounds to control environmental pests.
• a first object of the invention is to provide parasiticidal and pesticidal novel and inventive isoxazoline com ounds of formula (I):
• each of D 1 , D 2 , D 3 , D 4 and D 5 are independently N or C-A 1 , C-A 2 , C-A 3 , C-A 4 and C- A 5 , respectively, with the proviso that at most only three of D 1 , D 2 , D 3 , D 4 and D 5 may be simultaneously N;
• R 1 is halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, halocycloalkyl, alkylcycloalkyl or cycloalkylalkyl, each which is unsubstituted or substituted with one or more of hydroxy, amino, alkyl- or di(alkyl)amino, alkoxy, haloalkoxy, alkylthio or haloalkylthio;
• a 1 , A 2 , A 3 , A 4 and A 5 are independently hydrogen, halogen, hydroxy, amino, alkyl- or di(alkyl)amino, alkyl, cycloalkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, -CN or - O 2 ;
• B 1 , B 2 and B 3 are independently N or C-X;
• R 2 is hydrogen, halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, hydroxy, alkoxy, amino, alkyl- or dialkylamino, -CN or -NO2;
• R 3 , R 4 , R 5 and R 6 are each independently hydrogen, halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, amino, alkylamino, haloalkylamino, dialkylamino, dihaloalkylamino, hydroxyalkyl, alkoxyalkyl, thioalkyl or alkylthioalkyl; or
• R 7 and R 8 are independently hydrogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, aryl, heteroaryl, heterocyclyl, thioalkyl, thiohaloalkyl, alkylthioalkyl, hydroxyalkyl or alkoxyalkyl;
• Y is hydrogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, alkylcycloalkyl, cycloalkylalkyl, aryl, heterocyclyl or heteroaryl each of which is unsubstituted or substituted with one or more of halogen, hydroxy, amino, alkyl- or di(alkyl)amino, alkyl, cycloalkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, R 7 S(0)-, R 7 S(0) 2 -, R 7 C(0)-, R 7 R 8 NC(0)-, R 7 OC(0)-, R 7 C(0)0-, R 7 C(0)NR 8 - or -CN; or Y is
• each R 9 , R 10 are independently hydrogen, alkyl, haloalkyl, thioalkyl, alkylthioalkyl, hydroxyalkyl, alkoxylakyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, aryl, heteroaryl, heterocyclyl, R 7 S(0)-, R 7 S(0) 2 -, R 7 C(0)-, R 7 R 8 NC(0)-, R 7 OC(0)-, R 7 C(0)0-, R 7 C(0)NR 8 -; each R 11 is independently hydrogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, amino, alkylamino,
• haloalkylamino dialkylamino, dihaloalkylamino, hydroxyalkyl, alkoxyalkyl, thioalkyl or alkylthioalkyl;
• each R 12 and R 13 is independently hydrogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, amino, alkylamino, haloalkylamino, dialkylamino, dihaloalkylamino, hydroxyalkyl, alkoxyalkyl, thioalkyl or alkylthioalkyl; or
• W, Wi and Z are independently O, S or NR 7 ;
• L is a direct bond, -CR 3 R 4 -, -NR 8 - or -0-;
• a 1, 2 or 3;
• b is 1, 2 or 3;
• n 1, 2, 3 or 4;
• n 0, 1 or 2.
• D 1 , D 2 , D 3 , D 4 and D 5 are each C-A 1 , C-A 2 , C-A 3 , C-A 4 and C-A 5 , respectively.
• B 1 , B 2 and B 3 are C-H.
• R 1 is alkyl or haloalkyl.
• R 1 is C1-C4 alkyl or Ci-C 4 haloalkyl.
• R 1 is CF 3 .
• D 1 , D 2 , D 3 , D 4 and D 5 are each C-A 1 , C-A 2 , C- A 3 , C-A 4 and C-A 5 , respectively;
• a 2 , A 4 and A 5 are hydrogen; and
• a 1 and A 3 are independently halogen, alkyl or haloalkyl.
• a 2 is hydrogen; and
• a 1 and A 3 are independently halogen, C1-C4 alkyl or C1-C4 haloalkyl.
• D 1 , D 2 , D 3 , D 4 and D 5 are each C-A 1 , C-A 2 , C- A 3 , C-A 4 and C-A 5 , respectively;
• a 2 , A 4 and A 5 are hydrogen;
• a 1 and A 3 are independently halogen, C1-C4 alkyl or C1-C4 haloalkyl; and
• R 1 is C1-C4 alkyl or Ci-C4haloalkyl.
• a 2 , A 4 and A 5 are hydrogen;
• a 1 and A 3 are independently chloro, fluoro or CF 3 ; and R 1 is CF 3 .
• D 1 is N; D 2 , D 3 , D 4 and D 5 are each C-A 2 , C- A 3 , C-A 4 and C-A 5 , respectively; A 2 , A 4 and A 5 are hydrogen; A 3 is independently halogen, C1-C4 alkyl or C1-C4 haloalkyl; and R 1 is C1-C4 alkyl or Ci-C4haloalkyl.
• D 1 is N; D 2 , D 3 , D 4 and D 5 are each C-A 2 , C-A 3 , C-A 4 and C-A 5 , respectively; A 2 , A 4 and A 5 are hydrogen; A 3 is chloro, fluoro or CF 3 ; and R 1 is CF 3 .
• D 3 is N; D 1 , D 2 , D 4 and D 5 are each C-A 1 , C- A 2 , C-A 4 and C-A 5 , respectively; A 2 , A 4 and A 5 are hydrogen; A 1 is independently halogen, C1-C4 alkyl or C1-C4 haloalkyl; and R 1 is C1-C4 alkyl or Ci-C4haloalkyl.
• D 3 is N; D 1 , D 2 , D 4 and D 5 are each C-A 1 , C-A 2 , C-A 4 and C-A 5 , respectively; A 2 , A 4 and A 5 are hydrogen; A 1 is chloro, fluoro or CF 3 ; and R 1 is CF 3 .
• D 1 and D 3 are N; D 2 , D 4 and D 5 are each C-
• a , C-A and C-A are hydrogen; A is hydrogen, halogen, C1-C4 alkyl or C1-C4 haloalkyl; and R 1 is C1-C4 alkyl or Ci-C4haloalkyl.
• D 1 and D 3 are N; D 2 , D 4 and D 5 are each C-A 2 , C-A 4 and C-A 5 , respectively; A 4 and A 5 are hydrogen; A 2 is hydrogen, chloro, fluoro or CF 3 ; and R 1 is CF 3 .
• R 2 is hydrogen, halogen, alkyl or haloalkyl. In still another embodiment, R 2 is halogen, C1-C4 alkyl or Ci-C4haloalkyl. In another embodiment, R 2 is methyl or CF 3 . In another embodiment, R 2 is hydrogen.
• B 1 , B 2 and B 3 are C-H; D 1 , D 2 , D 3 , D 4 and D 5 are each respectively C-A 1 , C-A 2 , C-A 3 , C-A 4 or C-A 5 ; A 2 , A 4 and A 5 are hydrogen; A 1 and A 3 are independently chloro, fluoro or CF 3; R 1 is CF 3 ; and R 2 is methyl or CF 3 .
• B 1 , B 2 and B 3 are C-H; D 1 , D 2 , D 3 , D 4 and D 5 are each C-A 1 , C-A 2 , C-A 3 , C-A 4 and C-A 5 , respectively; A 2 , A 4 and A 5 are hydrogen; A 1 and A 3 are independently chloro, fluoro or CF 3; R 1 is CF 3 ; R 2 is methyl or CF 3 ; a is 1 or 2; and b is 1, 2 or 3.
• B 3 is C-H;
• D 1 , D 2 , D 3 , D 4 and D 5 are each respectively C-A 1 , C-A 2 , C-A 3 , C-A 4 and C-A 5
• Y is alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl or haloalkynyl each of which is unsubstituted or substituted with one or more of hydroxy, amino, alkyl- or di(alkyl)amino, alkyl, cycloalkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, R 7 S(0)-, R 7 S(0) 2 -, R 7 C(0)-, R 7 R 8 NC(0)-, R 7 OC(0)-, R 7 C(0)0-, R 7 C(0)NR 8 -, -CN or -N0 2 .
• Y is Ci-C 6 alkyl or Ci-C 6 haloalkyl. In still another embodiment, Y is methyl, ethyl, propyl, 1 -methylethyl, butyl, 1 -methylpropyl, 2- methylpropyl or 1 , 1 -dimethylethyl.
• Y is CF 3 , -CH 2 CF 3 , -CF 2 CF 3 , - CH 2 CH 2 CF 3 , -CH 2 CF 2 CF 3 ,— CF 2 CF 2 CF 3 ,— CH 2 CH 2 CH 2 CF 3 ,— CH 2 CH 2 CF 2 CF 3 ,—
• Y is Y-l, Y-2, Y-3, Y-4, Y-5, Y-6, Y-7, Y-8, Y-9, Y-10, Y-l l, Y-12 or Y-13.
• Y is Y-l, Y-4, Y-5, Y-6. In another embodiment, Y is Y is Y-2, Y-3, Y-7, Y-8 or Y-9. In another embodiment, Y is Y-10, Y-l l, Y-12 or Y-13.
• Y is Y-l, Y-4, Y-5 or Y-6, wherein W and Wi are
• R 9 , R 10 and R 11 are independently hydrogen, alkyl, haloalkyl, thioalkyl or alkylthioalkyl; R 12 and R 13 are hydrogen; and n is 1 or 2.
• Y is Y-2, Y-3, Y-7, Y-8 or Y-9, wherein W and Wi are O; R 9 , R 10 and R 11 are independently hydrogen, alkyl, haloalkyl, thioalkyl or alkylthioalkyl; R and R are hydrogen; and n is 1 or 2.
• Y is Y-l wherein W is O; and R 9 and R 10 are independently hydrogen, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 thioalkyl or Ci-C 4 alkylthioalkyl.
• Y is Y-l wherein W is O; and R 9 and R 10 are
• Y is Y-4, wherein W and Wi are O; R 9 and R 10 are independently hydrogen, Ci-C 4 alkyl or Ci-C 4 haloalkyl; R 12 and R 13 are hydrogen; and n is 1 or 2.
• Y is Y-4, wherein W and Wi are O; R 9 and R 10 are independently hydrogen or Ci-C 4 haloalkyl; R 12 and R 13 are hydrogen; and n is 1.
• Y is Y-4, wherein W and Wi are O; R 9 and R are independently hydrogen or -CH 2 CF 3 ; R 12 and R 13 are hydrogen; and n is 1.
• D 1 , D 2 , D 3 , D 4 and D 5 are each C-A 1 , C-A 2 , C-A 3 , C-A 4 and C-A 5 , respectively;
• a 2 , A 4 and A 5 are hydrogen;
• a 1 and A 3 are independently halogen, alkyl or haloalkyl;
• B 1 , B 2 and B 3 are C-H;
• R 1 is alkyl or haloalkyl;
• R 2 is hydrogen, halogen, alkyl or haloalkyl;
• Z is O
• L is a bond or -NR 8 -;
• R 3 , R 4 , R 5 and R 6 are each independently hydrogen, halogen, alkyl or haloalkyl; or
• D 1 , D 2 , D 3 , D 4 and D 5 are each C-A 1 , C-A 2 , C-A 3 , C-A 4 and C-A 5 , respectively;
• R 1 is alkyl or haloalkyl
• R 2 is hydrogen, halogen, alkyl or haloalkyl
• Z is O
• L is a bond or -NR 8 -;
• D 1 , D 2 , D 3 , D 4 and D 5 are each C-A 1 , C-A 2 , C-A 3 , C-A 4 and C-A 5 , respectively;
• a 2 , A 4 and A 5 are hydrogen;
• a 1 and A 3 are independently halogen, alkyl or haloalkyl;
• B 1 , B 2 and B 3 are C-H;
• R 1 is alkyl or haloalkyl;
• R 2 is hydrogen, halogen, alkyl or haloalkyl;
• Z is O
• L is a bond or -NR 8 -;
• Y is Y-l, Y-4, Y-5 or Y-6, in which W and Wi are O, R 9 , R 10 and R 11 are independently hydrogen, alkyl, haloalkyl, thioalkyl or alkylthioalkyl; R 12 and R 13 are hydrogen; and n is 1 or 2.
• D 1 , D 2 , D 3 , D 4 and D 5 are each C-A 1 , C-A 2 , C-A 3 , C-A 4 and
• a 2 , A 4 and A 5 are hydrogen;
• a 1 and A 3 are independently halogen, alkyl or haloalkyl;
• B 3 is C-H;
• R 1 is alkyl or haloalkyl
• R 2 is hydrogen, halogen, alkyl or haloalkyl
• Z is O
• L is a bond or -NR 8 -;
• Y is Y-l, Y-4, Y-5 or Y-6, in which W and Wi are O, R 9 , R 10 and R 11 are independently hydrogen, alkyl, haloalkyl, thioalkyl or alkylthioalkyl; R 12 and R 13 are hydrogen; and n is 1 or 2.
• D 1 , D 2 , D 3 , D 4 and D 5 are each C-A 1 , C-A 2 , C-A 3 , C-A 4 and C-A 5 , respectively;
• a 2 , A 4 and A 5 are hydrogen;
• a 1 and A 3 are independently halogen, alkyl or haloalkyl;
• B 1 , B 2 and B 3 are C-H;
• R 1 is alkyl or haloalkyl;
• R 2 is hydrogen, halogen, alkyl or haloalkyl;
• Z is O
• L is a bond or -NR 8 -;
• Y is Y is Y-2, Y-3, Y-7, Y-8 or Y-9, in which W and Wi are O;
• R 9 , R 10 and R 11 are independently hydrogen, alkyl, haloalkyl, thioalkyl or alkylthioalkyl;
• R 12 and R 13 are hydrogen; and
• n is 1 or 2.
• D 1 , D 2 , D 3 , D 4 and D 5 are each C-A 1 , C-A 2 , C-A 3 , C-A 4 and C-A 5 , respectively;
• a 2 , A 4 and A 5 are hydrogen;
• a 1 and A 3 are independently halogen, alkyl or haloalkyl;
• B 3 is C-H;
• R 1 is alkyl or haloalkyl;
• R 2 is hydrogen, halogen, alkyl or haloalkyl;
• Z is O
• L is a bond or -NR 8 -;
• Y is Y is Y-2, Y-3, Y-7, Y-8 or Y-9, in which W and Wi are O;
• R 9 , R 10 and R 11 are independently hydrogen, alkyl, haloalkyl, thioalkyl or alkylthioalkyl;
• R 12 and R 13 are hydrogen; and
• n is 1 or 2.
• D 1 , D 2 , D 3 , D 4 and D 5 are each C-A 1 , C- A 2 , C-A 3 , C-A 4 and C-A 5 , respectively;
• a 2 , A 4 and A 5 are hydrogen; and A 1 and A 3 are independently halogen, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl;
• B 1 , B 2 and B 3 are C-H;
• R 1 is C 1 -C 4 alkyl or Ci-C 4 haloalkyl;
• R 2 is hydrogen, halogen, C 1 -C 4 alkyl or Ci-C 4 haloalkyl;
• Z is O
• L is a bond or -NR 8 -;
• R 3 , R 4 , R 5 and R 6 are each hydrogen, halogen or Ci-C 4 alkyl; or
• Y is Ci-C 6 alkyl or Ci-C 6 haloalkyl.
• D 1 , D 2 , D 3 , D 4 and D 5 are each C-A 1 , C- A 2 , C-A 3 , C-A 4 and C-A 5 , respectively;
• a 2 , A 4 and A 5 are hydrogen; and A 1 and A 3 are independently halogen, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl;
• B 3 is C-H;
• R 1 is C 1 -C 4 alkyl or Ci-C 4 haloalkyl
• R 2 is hydrogen, halogen, C 1 -C 4 alkyl or Ci- C 4 haloalkyl;
• Z is O
• L is a bond or -NR 8 -;
• R 3 , R 4 , R 5 and R 6 are each hydrogen, halogen or Ci-C 4 alkyl; or
• Y is Ci-C 6 alkyl or Ci-C 6 haloalkyl.
• D 1 , D 2 , D 3 , D 4 and D 5 are each C-A 1 , C-A 2 , C-
• a 2 , A 4 and A 5 are hydrogen; and A 1 and A 3 are independently halogen, C 1 -C 4 alkyl or Ci-C 4 haloalkyl;
• B 1 , B 2 and B 3 are C-H;
• R 1 is C 1 -C 4 alkyl or Ci-C 4 haloalkyl;
• R 2 is hydrogen, halogen, C 1 -C 4 alkyl or Ci-C 4 haloalkyl;
• Z is O
• L is a bond or -NR 8 -;
• R 3 , R 4 , R 5 and R 6 are each hydrogen, halogen or Ci-C 4 alkyl; or
• Y is Y-l, Y-4, Y-5 or Y-6 in which W and Wi are O;
• R 9 , R 10 and R 11 are independently hydrogen, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 thioalkyl or Ci-C 4 alkylthio Ci-
• R 12 and R 13 are hydrogen; and n is 1 or 2.
• D 1 , D 2 , D 3 , D 4 and D 5 are each C-A 1 , C-A 2 , C- A 3 , C-A 4 and C-A 5 , respectively;
• a 2 , A 4 and A 5 are hydrogen; and A 1 and A 3 are independently halogen, C 1 -C 4 alkyl or Ci-C 4 haloalkyl;
• B 3 is C-H;
• R 1 is C 1 -C 4 alkyl or Ci-C 4 haloalkyl
• R 2 is hydrogen, halogen, C 1 -C 4 alkyl or Ci- C 4 haloalkyl;
• Z is O
• L is a bond or -NR 8 -;
• R 3 , R 4 , R 5 and R 6 are each hydrogen, halogen or Ci-C 4 alkyl; or
• Y is Y-l, Y-4, Y-5 or Y-6 in which W and Wi are O;
• R 9 , R 10 and R 11 are independently hydrogen, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 thioalkyl or Ci-C 4 alkylthio Ci-
• R 12 and R 13 are hydrogen; and n is 1 or 2.
• D 1 , D 2 , D 3 , D 4 and D 5 are each C-A 1 , C-A 2 , C-A 3 , C-A 4 and C-A 5 , respectively;
• a 2 , A 4 and A 5 are hydrogen; and A 1 and A 3 are independently halogen, C 1 -C 4 alkyl or Ci-C 4 haloalkyl;
• B 1 , B 2 and B 3 are C-H
• R 1 is C1-C4 alkyl or Ci-C 4 haloalkyl
• R 2 is hydrogen, halogen, C 1 -C 4 alkyl or Ci-C 4 haloalkyl
• Z is O
• L is a bond or -NR 8 -;
• each R 3 , R 4 , R 5 and R 6 are each hydrogen, halogen or Ci-C 4 alkyl; or
• Y is Y-2, Y-3, Y-7, Y-8 or Y-9, wherein W and Wi are O;
• R 9 , R 10 and R 11 are independently hydrogen, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 thioalkyl or Ci-C 4 alkylthio Ci- C 4 alkyl;
• R 12 and R 13 are hydrogen; and n is 1 or 2.
• D 1 , D 2 , D 3 , D 4 and D 5 are each C-A 1 , C-A 2 ,
• a 2 , A 4 and A 5 are hydrogen; and A 1 and A 3 are independently halogen, C 1 -C 4 alkyl or Ci-C 4 haloalkyl;
• B 3 is C-H;
• R 1 is C 1 -C 4 alkyl or Ci-C 4 haloalkyl
• R 2 is hydrogen, halogen, C 1 -C 4 alkyl or Ci-C 4 haloalkyl
• Z is O
• Y is Y-2, Y-3, Y-7, Y-8 or Y-9, wherein W and Wi are O;
• R 9 , R 10 and R 11 are independently hydrogen, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 thioalkyl or Ci-C 4 alkylthio Ci- C 4 alkyl;
• R 12 and R 13 are hydrogen; and n is 1 or 2.
• D 1 , D 2 , D 3 , D 4 and D 5 are each C-A 1 , C-A 2 , C-
• a 2 , A 4 and A 5 are hydrogen;
• a 1 and A 3 are independently chloro, fluoro or CF 3 ;
• R 1 is CF 3 ;
• B 1 , B 2 and B 3 are C-H
• R 2 is hydrogen, methyl or CF 3 ;
• Z is O
• L is a bond or -NH-
• R 3 , R 4 , R 5 and R 6 are each independently hydrogen or halogen; or
• Y is methyl, ethyl, propyl, 1 -methylethyl, butyl, 1 -methylpropyl, 2-methylpropyl or 1,1-dimethylethyl.
• D 1 , D 2 , D 3 , D 4 and D 5 are each C-A 1 , C-A 2 , C- A 3 , C-A 4 and C-A 5 , respectively;
• a 2 , A 4 and A 5 are hydrogen;
• a 1 and A 3 are independently chloro, fluoro or CF 3 ;
• R 1 is CF 3 ;
• B 3 is C-H;
• R 2 is hydrogen, methyl or CF 3 ;
• Z is O
• L is a bond or -NH-;
• Y is methyl, ethyl, propyl, 1 -methylethyl, butyl, 1 -methylpropyl, 2-methylpropyl or 1 , 1 -dimethylethyl.
• D 1 , D 2 , D 3 , D 4 and D 5 are each C-A 1 , C-A 2 , C- A 3 , C-A 4 and C-A 5 , respectively;
• a 2 , A 4 and A 5 are hydrogen;
• a 1 and A 3 are independently chloro, fluoro or CF 3 ;
• R 1 is CF 3 ;
• B 1 , B 2 and B 3 are C-H;
• R 2 is hydrogen, methyl or CF 3 ;
• Z is O
• L is a bond or -NH-
• R 3 , R 4 , R 5 and R 6 are each independently hydrogen or halogen; or
• Y is CF 3 , -CH 2 CF 3 , -
• CF 2 CF 3 , -CH 2 CH 2 CF 3 , -CH 2 CF 2 CF 3 , -CF 2 CF 2 CF 3 , -CH 2 CH 2 CH 2 CF 3 , -CH 2 CH 2 CF 2 CF 3 , -CH 2 CF 2 CF 3 or -CF 2 CF 2 CF 2 CF 3 .
• D 1 , D 2 , D 3 , D 4 and D 5 are each C-A 1 , C-A 2 , C-
• a 2 , A 4 and A 5 are hydrogen;
• a 1 and A 3 are independently chloro, fluoro or CF 3 ;
• R 1 is CF 3 ;
• B 3 is C-H;
• R 2 is hydrogen, methyl or CF 3 ;
• Z is O
• L is a bond or -NH-
• Y is CF 3 , -CH 2 CF 3 , -
• CF 2 CF 3 , -CH 2 CH 2 CF 3 , -CH 2 CF 2 CF 3 , -CF 2 CF 2 CF 3 , -CH 2 CH 2 CH 2 CF 3 , -CH 2 CH 2 CF 2 CF 3 , -CH 2 CF 2 CF 3 or -CF 2 CF 2 CF 2 CF 3 .
• D 1 , D 2 , D 3 , D 4 and D 5 are each C-A 1 , C-A 2 , C-A 3 , C-A 4 and C-A 5 , respectively;
• a 2 , A 4 and A 5 are hydrogen;
• a 1 and A 3 are independently chloro, fluoro or CF 3 ;
• R 1 is CF 3 ;
• B 1 , B 2 and B 3 are C-H;
• R 2 is methyl or CF 3 ;
• Z is O
• L is a bond or -NH-
• R 3 , R 4 , R 5 and R 6 are each independently hydrogen or halogen; or
• Y is Y-l wherein W is O; and R 9 and R 10 are independently hydrogen, -CH 2 CH 2 SH, - CH 2 CH 2 SCH 3 or -CH 2 CH 2 SCF 3 .
• D 1 , D 2 , D 3 , D 4 and D 5 are each C-A 1 , C-A 2 , C-A 3 , C-A 4 and C-A 5 , respectively;
• a 2 , A 4 and A 5 are hydrogen;
• a 1 and A 3 are independently chloro, fluoro or CF 3 ;
• R 1 is CF 3 ;
• B 1 , B 2 and B 3 are C-H;
• R 2 is methyl or CF 3 ;
• Z is O
• L is a bond or -NH-
• R 3 , R 4 , R 5 and R 6 are each independently hydrogen or halogen; or
• Y is Y-4, wherein W and Wi are O; R 9 and R 10 are independently hydrogen or -CH 2 CF 3 ; R 12 and R 13 are hydrogen; and n is 1.
• D 1 , D 2 , D 3 , D 4 and D 5 are each C-A 1 , C-A 2 , C-A 3 , C-A 4 and C-A 5 , respectively;
• a 2 , A 4 and A 5 are hydrogen;
• a 1 and A 3 are independently chloro, fluoro or CF 3 ;
• R 1 is CF 3 ;
• B 3 is C-H;
• R 2 is methyl or CF 3 ;
• Z is O
• L is a bond or -NH-
• R 3 , R 4 , R 5 and R 6 are each independently hydrogen or halogen; or
• Y is Y-l wherein W is O; and R 9 and R 10 are independently hydrogen, -CH 2 CH 2 SH, - CH 2 CH 2 SCH 3 or -CH 2 CH 2 SCF 3 .
• D 1 , D 2 , D 3 , D 4 and D 5 are each C-A 1 , C-A 2 , C-A 3 , C-A 4 and C-A 5 , respectively;
• a 2 , A 4 and A 5 are hydrogen;
• a 1 and A 3 are independently chloro, fluoro or CF 3 ;
• R 1 is CF 3 ;
• B 3 is C-H;
• R 2 is hydrogen
• Z is O
• L is a bond or -NH-
• R 3 , R 4 , R 5 and R 6 are each independently hydrogen or halogen; or
• Y is Y-4, wherein W and Wi are O; R 9 and R 10 are independently hydrogen or -CH 2 CF 3 ; R 12 and R 13 are hydrogen; and n is 1.
• the invention provides parasiticidal and pesticidal isoxazoline compounds of formula (IA):
• Ri is halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, halocycloalkyl, alkylcycloalkyl or cycloalkylalkyl, each which is unsubstituted or substituted with one or more of hydroxy, amino, alkyl- or di(alkyl)amino, alkoxy, haloalkoxy, alkylthio or haloalkylthio;
• a 1 and A 3 are independently hydrogen, halogen, hydroxy, amino, alkyl- or di(alkyl)amino, alkyl, cycloalkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, -CN or -NO 2 ;
• B 1 and B 2 are independently N or C-X;
• R 2 is hydrogen, halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, hydroxy, alkoxy, amino, alkyl- or dialkylamino, -CN or -NO 2 ;
• R 3 , R 4 , R 5 and R 6 are each independently hydrogen, halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, amino, alkylamino, haloalkylamino, dialkylamino, dihaloalkylamino, hydroxyalkyl, alkoxyalkyl, thioalkyl or alkylthioalkyl; or
• R 7 and R 8 are independently hydrogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, aryl, heteroaryl, heterocyclyl, thioalkyl, thiohaloalkyl, alkylthioalkyl, hydroxyalkyl or alkoxyalkyl;
• Y is hydrogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, alkylcycloalkyl, cycloalkylalkyl, aryl, heterocyclyl or heteroaryl each of which is unsubstituted or substituted with one or more of halogen, hydroxy, amino, alkyl- or di(alkyl)amino, alkyl, cycloalkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, R 7 S(0)-, R 7 S(0) 2 -, R 7 C(0)-, R 7 R 8 NC(0)-, R 7 OC(0)-, R 7 C(0)0-, R 7 C(0)NR 8 -, -CN or -N0
• each R 9 , R 10 are independently hydrogen, alkyl, haloalkyl, thioalkyl, alkylthioalkyl, hydroxyalkyl, alkoxylakyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, aryl, heteroaryl, heterocyclyl, R 7 S(0)-, R 7 S(0) 2 -, R 7 C(0)-, R 7 R 8 NC(0)-, R 7 OC(0)-, R 7 C(0)0-, R 7 C(0)NR 8 -; each R 11 is independently hydrogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, amino, alkylamino,
• haloalkylamino dialkylamino, dihaloalkylamino, hydroxyalkyl, alkoxyalkyl, thioalkyl or alkylthioalkyl;
• each R 12 and R 13 is independently hydrogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, amino, alkylamino, haloalkylamino, dialkylamino, dihaloalkylamino, hydroxyalkyl, alkoxyalkyl, thioalkyl or alkylthioalkyl; or
• W, Wi and Z are independently O, S or NR 7 ;
• L is a direct bond, -CR 3 R 4 -, -NR 8 - or -0-;
• a 1, 2 or 3;
• b is 1, 2 or 3;
• n 1, 2, 3 or 4;
• n 0, 1 or 2.
• B 1 and B 2 are CH.
• R 1 is alkyl or haloalkyl. In another embodiment, R 1 is C1-C4 alkyl or Ci-C4haloalkyl. In another embodiment, R 1 is CF 3 .
• a 1 and A 3 are independently halogen, alkyl or haloalkyl. In an embodiment, A 1 and A 3 are independently halogen, C1-C4 alkyl or C1-C4 haloalkyl.
• a 1 and A 3 are independently halogen, C1-C4 alkyl or C1-C4 haloalkyl; and R 1 is C1-C4 alkyl or Ci-C4haloalkyl.
• a 1 and A 3 are independently chloro, fluoro or CF 3 ; and R 1 is CF 3 .
• R 2 is halogen, alkyl or haloalkyl.
• R 2 is hydrogen, halogen, C1-C4 alkyl or Ci-C4haloalkyl.
• R 2 is methyl or CF 3 .
• a 1 and A 3 are independently chloro, fluoro or CF 3; R 1 is CF 3 ; and R 2 is methyl or CF 3 .
• a 1 and A 3 are independently chloro, fluoro or CF 3; R 1 is CF 3 ; R 2 is methyl or CF 3 ; a is 1 or 2; and b is 1, 2 or 3.
• Y is alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl or haloalkynyl each of which is unsubstituted or substituted with one or more of hydroxy, amino, alkyl- or di(alkyl)amino, alkyl, cycloalkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, R 7 S(0)-, R 7 S(0) 2 -, R 7 C(0)-, R 7 R 8 NC(0)-, R 7 OC(0)-, R 7 C(0)0-, R 7 C(0)NR 8 -, -CN or -N0 2 .
• Y is Ci-C 6 alkyl or Ci-C 6 haloalkyl. In still another embodiment, Y is methyl, ethyl, propyl, 1 -methylethyl, butyl, 1 -methylpropyl, 2- methylpropyl or 1 , 1 -dimethylethyl.
• Y is CF 3 , -CH 2 CF 3 , -CF 2 CF 3 , - CH 2 CH 2 CF 3 , -CH 2 CF 2 CF 3 , -CF 2 CF 2 CF 3 , -CH 2 CH 2 CH 2 CF 3 , -CH 2 CH 2 CF 2 CF 3 , - CH 2 CF 2 CF 2 CF 3 or -CF 2 CF 2 CF 2 CF 3 .
• Y is Y-l, Y-2, Y-3, Y-4, Y-5, Y-6, Y-7, Y-8, Y-9, Y-10, Y-l l, Y-12 or Y-13.
• Y is Y-l, Y-4, Y-5, Y-6. In another embodiment, Y is Y is Y-2, Y-3, Y-7, Y-8 or Y-9. In yet another embodiment, Y is Y-2, Y-3, Y-7, Y-8 or Y-9. In another embodiment, Y is Y- 10, Y- 11 , Y- 12 or Y- 13.
• Y is Y-l, Y-4, Y-5 or Y-6, wherein W and Wi are 0; R 9 , R 10 and R 11 are independently hydrogen, alkyl, haloalkyl, thioalkyl or
• alkylthioalkyl R 12 and R 13 are hydrogen; and n is 1 or 2.
• Y is Y-2, Y-3, Y-7, Y-8 or Y-9, wherein W and Wi are O; R 9 , R 10 and R 11 are independently hydrogen, alkyl, haloalkyl, thioalkyl or alkylthioalkyl; R 12 and R 13 are hydrogen; and n is 1 or 2.
• Y is Y-l wherein W is O; and R 9 and R 10 are independently hydrogen, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 thioalkyl or Ci-C 4 alkylthioalkyl.
• Y is Y-l wherein W is O; and R 9 and R 10 are independently hydrogen, - CH 2 CH 2 SH, -CH 2 CH 2 SCH 3 or -CH 2 CH 2 SCF 3 .
• Y is Y-4, wherein W and Wi are O; R 9 and R 10 are independently hydrogen, Ci-C 4 alkyl or Ci-C 4 haloalkyl; R 12 and R 13 are hydrogen; and n is 1 or 2.
• Y is Y-4, wherein W and Wi are O; R 9 and R 10 are independently hydrogen or Ci-C 4 haloalkyl; R 12 and R 13 are hydrogen; and n is 1.
• Y is Y-4, wherein W and Wi are O; R 9 and R 10 are independently hydrogen or -CH 2 CF 3 ; R 12 and R 13 are hydrogen; and n is 1.
• a 1 and A 3 are independently halogen, alkyl or haloalkyl
• B 1 and B 2 are CH;
• R 1 is alkyl or haloalkyl
• R 2 is hydrogen, halogen, alkyl or haloalkyl
• Z is O
• L is a bond or -NR 8 -;
• R 3 , R 4 , R 5 and R 6 are each independently hydrogen, halogen, alkyl or haloalkyl; or
• a 1 and A 3 are independently halogen, alkyl or haloalkyl
• R 1 is alkyl or haloalkyl
• R 2 is hydrogen, halogen, alkyl or haloalkyl
• Z is O
• L is a bond or -NR 8 -;
• a 1 and A 3 are independently halogen, alkyl or haloalkyl; B 1 and B 2 are C-H;
• R 1 is alkyl or haloalkyl
• R 2 is hydrogen, halogen, alkyl or haloalkyl
• Z is O
• L is a bond or -NR 8 -;
• Y is Y-l, Y-4, Y-5 or Y-6, in which W and Wi are O, R 9 , R 10 and R 11 are independently hydrogen, alkyl, haloalkyl, thioalkyl or alkylthioalkyl; R 12 and R 13 are hydrogen; and n is 1 or 2.
• a 1 and A 3 are independently halogen, alkyl or haloalkyl
• R 1 is alkyl or haloalkyl
• R 2 is hydrogen, halogen, alkyl or haloalkyl
• Z is O
• L is a bond or -NR 8 -;
• Y is Y-l, Y-4, Y-5 or Y-6, in which W and Wi are O, R 9 , R 10 and R 11 are independently hydrogen, alkyl, haloalkyl, thioalkyl or alkylthioalkyl; R 12 and R 13 are hydrogen; and n is 1 or 2.
• a 1 and A 3 are independently halogen, alkyl or haloalkyl; R 1 is alkyl or haloalkyl;
• B 1 and B 2 are C-H
• R 2 is hydrogen, halogen, alkyl or haloalkyl
• Z is O
• L is a bond or -NR 8 -;
• Y is Y is Y-2, Y-3, Y-7, Y-8 or Y-9, in which W and Wi are O;
• R 9 , R 10 and R 11 are independently hydrogen, alkyl, haloalkyl, thioalkyl or alkylthioalkyl;
• R 12 and R 13 are hydrogen; and
• n is 1 or 2.
• a 1 and A 3 are independently halogen, alkyl or haloalkyl; R 1 is alkyl or haloalkyl;
• R 2 is hydrogen, halogen, alkyl or haloalkyl
• Z is O
• L is a bond or -NR 8 -;
• R 3 , R 4 , R 5 and R 6 are each independently hydrogen, halogen, alkyl or haloalkyl; or R 3 and R 4 together with the carbon atom to which they are bonded together form
• Y is Y is Y-2, Y-3, Y-7, Y-8 or Y-9, in which W and Wi are O;
• R 9 , R 10 and R 11 are independently hydrogen, alkyl, haloalkyl, thioalkyl or alkylthioalkyl;
• R 12 and R 13 are hydrogen; and
• n is 1 or 2.
• a 1 and A 3 are independently halogen, C1-C4 alkyl or C1-C4 haloalkyl;
• B 1 and B 2 are C-H
• R 1 is C1-C4 alkyl or Ci-C 4 haloalkyl
• R 2 is hydrogen, halogen, C1-C4 alkyl or Ci-C 4 haloalkyl
• Z is O
• L is a bond or -NR 8 -;
• R 3 , R 4 , R 5 and R 6 are each hydrogen, halogen or C1-C4 alkyl; or
• Y is Ci-C 6 alkyl or Ci-C 6 haloalkyl.
• a 1 and A 3 are independently halogen, C1-C4 alkyl or Ci-C4 haloalkyl;
• R 1 is C1-C4 alkyl or Ci-C 4 haloalkyl
• R 2 is hydrogen, halogen, C1-C4 alkyl or Ci-C4haloalkyl
• Z is O
• L is a bond or -NR 8 -;
• R 3 , R 4 , R 5 and R 6 are each hydrogen, halogen or C1-C4 alkyl; or
• Y is Ci-C 6 alkyl or Ci-C 6 haloalkyl.
• a 1 and A 3 are independently halogen, C1-C4 alkyl or Ci-C4 haloalkyl;
• B 1 and B 2 are C-H
• R 1 is C1-C4 alkyl or Ci-C 4 haloalkyl
• R 2 is hydrogen, halogen, C1-C4 alkyl or Ci-C4haloalkyl
• Z is O
• L is a bond or -NR 8 -;
• R 3 , R 4 , R 5 and R 6 are each hydrogen, halogen or C1-C4 alkyl; or
• Y is Y-l, Y-4, Y-5 or Y-6 in which W and Wi are O;
• R 9 , R 10 and R 11 are independently hydrogen, Ci-C4alkyl, Ci-C4haloalkyl, Ci-C4thioalkyl or Ci-C4alkylthio Ci- C4alkyl;
• R 12 and R 13 are hydrogen;
• n 1 or 2.
• a 1 and A 3 are independently halogen, C1-C4 alkyl or Ci-C4 haloalkyl;
• R 1 is C1-C4 alkyl or Ci-C 4 haloalkyl
• R 2 is hydrogen, halogen, C1-C4 alkyl or Ci-C4haloalkyl
• Z is O
• L is a bond or -NR 8 -;
• R 3 , R 4 , R 5 and R 6 are each hydrogen, halogen or C1-C4 alkyl; or
• Y is Y-l, Y-4, Y-5 or Y-6 in which W and Wi are O;
• R 9 , R 10 and R 11 are independently hydrogen, Ci-C4alkyl, Ci-C4haloalkyl, Ci-C4thioalkyl or Ci-C4alkylthio Ci- C4alkyl;
• R 12 and R 13 are hydrogen;
• n 1 or 2.
• a 1 and A 3 are independently halogen, Ci- C4 alkyl or Ci-C4 haloalkyl;
• B 1 and B 2 are C-H
• R 1 is C1-C4 alkyl or Ci-C 4 haloalkyl
• R 2 is hydrogen, halogen, C1-C4 alkyl or Ci-C4haloalkyl
• Z is O
• L is a bond or -NR 8 -;
• each R 3 , R 4 , R 5 and R 6 are each hydrogen, halogen or C1-C4 alkyl; or
• Y is Y-2, Y-3, Y-7, Y-8 or Y-9, wherein W and Wi are O;
• R 9 , R 10 and R 11 are independently hydrogen, Ci-C4alkyl, Ci-C4haloalkyl, Ci-C4thioalkyl or Ci-C4alkylthio Ci- C4alkyl;
• R 12 and R 13 are hydrogen; and
• n is 1 or 2.
• a 1 and A 3 are independently halogen, Ci- C 4 alkyl or Ci-C 4 haloalkyl;
• R 1 is C1-C4 alkyl or Ci-C 4 haloalkyl
• R 2 is hydrogen, halogen, C1-C4 alkyl or Ci-C 4 haloalkyl
• Z is O
• L is a bond or -NR 8 -;
• each R 3 , R 4 , R 5 and R 6 are each hydrogen, halogen or C1-C4 alkyl; or
• Y is Y-2, Y-3, Y-7, Y-8 or Y-9, wherein W and Wi are O;
• R 9 , R 10 and R 11 are independently hydrogen, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 thioalkyl or Ci-C 4 alkylthio Ci- C 4 alkyl;
• R 12 and R 13 are hydrogen; and n is 1 or 2.
• a 1 and A 3 are independently chloro, fluoro or
• B 1 and B 2 are C-H
• R 1 is CF 3 ;
• R 2 is hydrogen, methyl or CF 3 ;
• Z is O
• L is a bond or -NH-
• R 3 , R 4 , R 5 and R 6 are each independently hydrogen or halogen; or
• Y is methyl, ethyl, propyl, 1 -methylethyl, butyl, 1 -methylpropyl, 2-methylpropyl or 1 , 1 -dimethylethyl.
• a 1 and A 3 are independently chloro, fluoro or
• R 1 is CF 3 ;
• R 2 is hydrogen, methyl or CF 3 ;
• Z is O
• L is a bond or -NH-
• R 3 , R 4 , R 5 and R 6 are each independently hydrogen or halogen; or
• Y is methyl, ethyl, propyl, 1 -methylethyl, butyl, 1 -methylpropyl, 2-methylpropyl or 1 , 1 -dimethylethyl.
• a 1 and A 3 are independently chloro, fluoro or
• B 1 and B 2 are C-H
• R 1 is CF 3 ;
• R 2 is hydrogen, methyl or CF 3 ;
• Z is O
• L is a bond or -NH-
• R 3 , R 4 , R 5 and R 6 are each independently hydrogen or halogen; or
• Y is CF 3 , -CH 2 CF 3 , -
• CF 2 CF 3 , -CH 2 CH 2 CF 3 , -CH 2 CF 2 CF 3 , -CF 2 CF 2 CF 3 , -CH 2 CH 2 CH 2 CF 3 , -CH 2 CH 2 CF 2 CF 3 , -CH 2 CF 2 CF 3 or -CF 2 CF 2 CF 2 CF 3 .
• a 1 and A 3 are independently chloro, fluoro or
• R 1 is CF 3 ;
• R 2 is hydrogen, methyl or CF 3 ;
• Z is O;
• L is a bond or -NH-
• R 3 , R 4 , R 5 and R 6 are each independently hydrogen or halogen; or
• Y is CF 3 , -CH 2 CF 3 , -
• CF 2 CF 3 , -CH 2 CH 2 CF 3 , -CH 2 CF 2 CF 3 , -CF 2 CF 2 CF 3 , -CH 2 CH 2 CH 2 CF 3 , -CH 2 CH 2 CF 2 CF 3 , -CH 2 CF 2 CF 3 or -CF 2 CF 2 CF 2 CF 3 .
• a 1 and A 3 are independently chloro, fluoro or CF 3 ;
• B 1 and B 2 are C-H
• R 1 is CF 3 ;
• R 2 is hydrogen, methyl or CF 3 ;
• Z is O
• L is a bond or -NH-
• R 3 , R 4 , R 5 and R 6 are each independently hydrogen or halogen; or
• Y is Y-l wherein W is O; and R 9 and R 10 are independently hydrogen, -CH 2 CH 2 SH, - CH 2 CH 2 SCH 3 or -CH 2 CH 2 SCF 3 .
• a 1 and A 3 are independently chloro, fluoro or CF 3 ;
• R 1 is CF 3 ;
• R 2 is hydrogen, methyl or CF 3 ;
• Z is O
• L is a bond or -NH-;
• Y is Y-l wherein W is O; and R 9 and R 10 are independently hydrogen, -CH 2 CH 2 SH, CH 2 CH 2 SCH 3 or -CH 2 CH 2 SCF 3 .
• a 1 and A 3 are independently chloro, fluoro or CF 3 ;
• B 1 and B 2 are C-H
• R 1 is CF 3 ;
• R 2 is methyl or CF 3 ;
• Z is O
• L is a bond or -NH-
• R 3 , R 4 , R 5 and R 6 are each independently hydrogen or halogen; or
• Y is Y-4, wherein W and Wi are O; R 9 and R 10 are independently hydrogen or -CH 2 CF 3 ; R 12 and R 13 are hydrogen; and n is 1.
• a 1 and A 3 are independently chloro, fluoro or CF 3 ;
• R 1 is CF 3 ;
• R 2 is hydrogen, methyl or CF 3 ;
• Z is O
• L is a bond or -NH-
• R 3 , R 4 , R 5 and R 6 are each independently hydrogen or halogen; or
• Y is Y-4, wherein W and Wi are O; R 9 and R 10 are independently hydrogen or -CH 2 CF 3 ; R 12 and R 13 are hydrogen; and n is 1.
• the invention provides parasiticidal and pesticidal isoxazoline compounds of formula (IB):
• Ri is alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl;
• a 1 and A 3 are independently hydrogen, halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl or haloalkynyl;
• B 1 and B 2 are independently N or C-X;
• R 2 is hydrogen, halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl or
• R 3 , R 4 , R 3' , R 4' , R 5 , R 6 , R 5 and R 6' are each independently hydrogen, halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl or haloalkynyl; or
• R 7 and R 8 are independently hydrogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, aryl, heteroaryl, heterocyclyl, thioalkyl, thiohaloalkyl, alkylthioalkyl, hydroxyalkyl or alkoxyalkyl;
• Y is hydrogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, alkylcycloalkyl, cycloalkylalkyl, aryl, heterocyclyl or heteroaryl each of which is unsubstituted or substituted with one or more of halogen, hydroxy, amino, alkyl- or di(alkyl)amino, alkyl, cycloalkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, R 7 S(0)-, R 7 S(0) 2 -, R 7 C(0)-, R 7 R 8 NC(0)-, R 7 OC(0)-, R 7 C(0)0-, R 7 C(0)NR 8 -, -CN or -N0
• each R 9 , R 10 are independently hydrogen, alkyl, haloalkyl, thioalkyl, alkylthioalkyl, hydroxyalkyl, alkoxylakyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, aryl, heteroaryl, heterocyclyl, R 7 S(0)-, R 7 S(0) 2 -, R 7 C(0)-, R 7 R 8 NC(0)-, R 7 OC(0)-, R 7 C(0)0-, R 7 C(0)NR 8 -;
• each R 11 is independently hydrogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, amino, alkylamino,
• haloalkylamino dialkylamino, dihaloalkylamino, hydroxyalkyl, alkoxyalkyl, thioalkyl or alkylthioalkyl;
• each R 12 and R 13 is independently hydrogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, amino, alkylamino, haloalkylamino, dialkylamino, dihaloalkylamino, hydroxyalkyl, alkoxyalkyl, thioalkyl or alkylthioalkyl; or
• W, Wi and Z are independently O, S or NR 7 ;
• L is a direct bond, -CR 3 R 4 -, -NR 8 - or -0-;
• n 1, 2, 3 or 4;
• n 0, 1 or 2.
• R 1 is alkyl or haloalkyl. In another embodiment, R 1 is C1-C4 alkyl or Ci-C 4 haloalkyl. In another embodiment, R 1 is CF 3 .
• a 1 and A 3 are independently halogen, alkyl or haloalkyl. In an embodiment, A 1 and A 3 are independently halogen, C1-C4 alkyl or C1-C4 haloalkyl.
• a 1 and A 3 are independently halogen, C1-C4 alkyl or C1-C4 haloalkyl; and R 1 is C1-C4 alkyl or Ci-C 4 haloalkyl.
• a 1 and A 3 are independently chloro, fluoro or CF3; and R 1 is CF3.
• B 1 and B 2 are C-H.
• R 2 is hydrogen, halogen, alkyl or haloalkyl.
• R 2 is hydrogen, halogen, C 1 -C 4 alkyl or Ci-C 4 haloalkyl. In another embodiment, R 2 is methyl or CF 3 .
• a 1 and A 3 are independently chloro, fluoro or CF 3; R 1 is CF 3 ; and R 2 is methyl or CF 3 .
• a 1 and A 3 are independently chloro, fluoro or
• R 1 is CF 3 ;
• R 2 is methyl or CF 3 ;
• a is 1 or 2; and
• b is 1, 2 or 3.
• a 1 and A 3 are independently chloro, fluoro or CF 3; B 1 and B 2 are C-H; R 1 is CF 3 ; and R 2 is hydrogen, methyl or CF 3 .
• a 1 and A 3 are independently chloro, fluoro or CF 3; B 1 and B 2 are C-H; R 1 is CF 3 ; R 2 is hydrogen, methyl or CF 3 ; a is 1 or 2; and b is 1, 2 or 3.
• a 1 and A 3 are independently chloro, fluoro or CF 3 .
• R 1 is CF 3 ; and
• R 2 is hydrogen, methyl or CF 3 .
• a 1 and A 3 are independently chloro, fluoro or CF 3 .
• R 1 is CF 3 ;
• R 2 is hydrogen, methyl or CF 3 ;
• a is 1 or 2; and
• b is 1, 2 or 3.
• Y is alkyl, haloalkyl, alkenyl
• haloalkenyl, alkynyl or haloalkynyl each of which is unsubstituted or substituted with one or more of hydroxy, amino, alkyl- or di(alkyl)amino, alkyl, cycloalkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, R 7 S(0)-, R 7 S(0) 2 -, R 7 C(0)-, R 7 R 8 NC(0)-, R 7 OC(0)-, R 7 C(0)0-, R 7 C(0)NR 8 -, -CN or -N0 2 .
• Y is Ci-C 6 alkyl or Ci-C 6 haloalkyl. In still another embodiment, Y is methyl, ethyl, propyl, 1 -methylethyl, butyl, 1 -methylpropyl, 2- methylpropyl or 1 , 1 -dimethylethyl.
• Y is CF 3 , -CH 2 CF 3 , -CF 2 CF 3 , - CH 2 CH 2 CF 3 , -CH 2 CF 2 CF 3 ,— CF 2 CF 2 CF 3 ,— CH 2 CH 2 CH 2 CF 3 ,— CH 2 CH 2 CF 2 CF 3 ,— CH 2 CF 2 CF 2 CF 3 or -CF 2 CF 2 CF 2 CF 3 .
• Y is Y-l, Y-2, Y-3, Y-4, Y-5, Y-6, Y-7, Y-8, Y-9, Y-10, Y-l l, Y-12 or Y-13.
• Y is Y-l, Y-4, Y-5, Y-6.
• Y is Y is Y-2, Y-3, Y-7, Y-8 or Y-9.
• Y is Y-10, Y-l 1, Y-12 or Y-13.
• Y is Y-l, Y-4, Y-5 or Y-6, wherein W and Wi are 0; R 9 , R 10 and R 11 are independently hydrogen, alkyl, haloalkyl, thioalkyl or
• alkylthioalkyl R 12 and R 13 are hydrogen; and n is 1 or 2.
• Y is Y-2, Y-3, Y-7, Y-8 or Y-9, wherein W and Wi are O; R 9 , R 10 and R 11 are independently hydrogen, alkyl, haloalkyl, thioalkyl or alkylthioalkyl; R 12 and R 13 are hydrogen; and n is 1 or 2.
• Y is Y-l wherein W is O; and R 9 and R 10 are independently hydrogen, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 thioalkyl or Ci- C 4 alkylthioalkyl.
• Y is Y-l wherein W is O; and R 9 and R 10 are independently hydrogen, -CH 2 CH 2 SH, -CH 2 CH 2 SCH 3 or -CH 2 CH 2 SCF 3 .
• Y is Y-4, wherein W and Wi are O; R 9 and R 10 are independently hydrogen, Ci-C 4 alkyl or Ci-C 4 haloalkyl; R 12 and R 13 are hydrogen; and n is 1 or 2.
• Y is Y-4, wherein W and Wi are O; R 9 and R 10 are independently hydrogen or Ci-C 4 haloalkyl; R 12 and R 13 are hydrogen; and n is 1.
• Y is Y-4, wherein W and Wi are O; R 9 and R 10 are independently hydrogen or -CH 2 CF 3 ; R 12 and R 13 are hydrogen; and n is 1.
• a 1 and A 3 are independently halogen, alkyl or haloalkyl
• B 1 and B 2 are C-H
• R 1 is alkyl or haloalkyl
• R 2 is hydrogen, halogen, alkyl or haloalkyl
• Z is O
• L is a bond or -NR 7 -;
• R 3 , R 4 , R 3' , R 4' , R 5 , R 6 , R 5 and R 6' are each independently hydrogen, halogen, alkyl or haloalkyl; or
• a 1 and A 3 are independently halogen, alkyl or haloalkyl
• R 1 is alkyl or haloalkyl
• R 2 is hydrogen, halogen, alkyl or haloalkyl
• Z is O
• L is a bond or -NR 7 -;
• R 3 , R 4 , R 3 , R 4 , R 5 , R 6 , R 5 and R 6 are each independently hydrogen, halogen, alkyl or haloalkyl; or
• a 1 and A 3 are independently halogen, alkyl or haloalkyl
• B 1 and B 2 are C-H
• R 1 is alkyl or haloalkyl
• R 2 is hydrogen, halogen, alkyl or haloalkyl
• Z is O
• L is a bond or -NR 7 -;
• Y is Y-l, Y-4, Y-5 or Y-6, in which W and Wi are O, R 9 , R 10 and R 11 are independently hydrogen, alkyl, haloalkyl, thioalkyl or alkylthioalkyl; R 12 and R 13 are hydrogen; and n is 1 or 2.
• a 1 and A 3 are independently halogen, alkyl or haloalkyl
• R 1 is alkyl or haloalkyl
• R 2 is hydrogen, halogen, alkyl or haloalkyl
• Z is O
• L is a bond or -NR 7 -;
• Y is Y-l, Y-4, Y-5 or Y-6, in which W and Wi are O, R 9 , R 10 and R 11 are independently hydrogen, alkyl, haloalkyl, thioalkyl or alkylthioalkyl; R 12 and R 13 are hydrogen; and n is 1 or 2.
• a 1 and A 3 are independently halogen, alkyl or haloalkyl
• B 1 and B 2 are C-H
• R 1 is alkyl or haloalkyl
• R 2 is hydrogen, halogen, alkyl or haloalkyl
• Z is O
• L is a bond or -NR 7 -;
• R 3 , R 4 , R 3' , R 4' , R 5 , R 6 , R 5' and R 6' are each independently hydrogen, halogen, alkyl or haloalkyl; or
• Y is Y is Y-2, Y-3, Y-7, Y-8 or Y-9, in which W and Wi are O;
• R 9 , R 10 and R 11 are independently hydrogen, alkyl, haloalkyl, thioalkyl or alkylthioalkyl;
• R and R are hydrogen; and
• n is 1 or 2.
• a 1 and A 3 are independently halogen, alkyl or haloalkyl
• R 1 is alkyl or haloalkyl
• R 2 is hydrogen, halogen, alkyl or haloalkyl
• Z is O
• L is a bond or -NR 7 -;
• R 3 , R 4 , R 3' , R 4' , R 5 , R 6 , R 5' and R 6' are each independently hydrogen, halogen, alkyl or haloalkyl; or
• Y is Y is Y-2, Y-3, Y-7, Y-8 or Y-9, in which W and Wi are O;
• R 9 , R 10 and R 11 are independently hydrogen, alkyl, haloalkyl, thioalkyl or alkylthioalkyl;
• R 12 and R 13 are hydrogen; and
• n is 1 or 2.
• a 1 and A 3 are independently halogen, C1-C4 alkyl or C1-C4 haloalkyl;
• B 1 and B 2 are C-H
• R 1 is C1-C4 alkyl or Ci-C 4 haloalkyl
• R 2 is hydrogen, halogen, C1-C4 alkyl or Ci-C 4 haloalkyl
• Z is O
• L is a bond or -NR 7 -;
• Y is Ci-C 6 alkyl or Ci-C 6 haloalkyl.
• a 1 and A 3 are independently halogen, C1-C4 alkyl or Ci-C 4 haloalkyl;
• R 1 is C1-C4 alkyl or Ci-C 4 haloalkyl
• R 2 is hydrogen, halogen, C1-C4 alkyl or Ci-C 4 haloalkyl
• Z is O
• L is a bond or -NR 7 -;
• Y is Ci-C 6 alkyl or Ci-C 6 haloalkyl.
• a 1 and A 3 are independently halogen, C1-C4 alkyl or Ci-C 4 haloalkyl;
• B 1 and B 2 are C-H
• R 1 is C1-C4 alkyl or Ci-C 4 haloalkyl
• R 2 is hydrogen, halogen, C1-C4 alkyl or Ci-C 4 haloalkyl
• Z is O
• L is a bond or -NR 7 -;
• Y is Y-l, Y-4, Y-5 or Y-6 in which W and Wi are O;
• R 9 , R 10 and R 11 are independently hydrogen, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 thioalkyl or Ci-C 4 alkylthio Ci- C 4 alkyl;
• R and R are hydrogen; and n is 1 or 2.
• a 1 and A 3 are independently halogen, Ci-C 4 alkyl or Ci-C 4 haloalkyl;
• R 1 is Ci-C 4 alkyl or Ci-C 4 haloalkyl
• R 2 is hydrogen, halogen, Ci-C 4 alkyl or Ci-C 4 haloalkyl
• Z is O
• L is a bond or -NR 7 -;
• R 5 and R 6 and/or R 5 and R 6 together with the carbon atom to which they are bonded together form C W, with the proviso that at least one of R 3 and R 4 , R 3 and R 4 , R 5 and R 6 , or
• Y is Y-l, Y-4, Y-5 or Y-6 in which W and Wi are O;
• R 9 , R 10 and R 11 are independently hydrogen, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 thioalkyl or Ci-C 4 alkylthio Ci- C 4 alkyl;
• R 12 and R 13 are hydrogen; and n is 1 or 2.
• a 1 and A 3 are independently halogen, Ci- C 4 alkyl or Ci-C 4 haloalkyl;
• B 1 and B 2 are C-H
• R 1 is Ci-C 4 alkyl or Ci-C 4 haloalkyl
• R 2 is hydrogen, halogen, Ci-C 4 alkyl or Ci-C 4 haloalkyl
• Z is O
• L is a bond or -NR 7 -;
• R 5 and R 6 and/or R 5 and R 6 together with the carbon atom to which they are bonded together form C W, with the proviso that at least one of R 3 and R 4 , R 3 and R 4 , R 5 and R 6 , or
• Y is Y-2, Y-3, Y-7, Y-8 or Y-9, wherein W and Wi are O;
• R 9 , R 10 and R 11 are independently hydrogen, Ci-C4alkyl, Ci-C4haloalkyl, Ci-C4thioalkyl or Ci-C4alkylthio Ci- C4alkyl;
• R 12 and R 13 are hydrogen; and n is 1 or 2.
• a 1 and A 3 are independently halogen, Ci- C4 alkyl or Ci-C4 haloalkyl;
• R 1 is C1-C4 alkyl or Ci-C 4 haloalkyl
• R 2 is hydrogen, halogen, C1-C4 alkyl or Ci-C4haloalkyl
• Z is O
• L is a bond or -NR 7 -;
• Y is Y-2, Y-3, Y-7, Y-8 or Y-9, wherein W and Wi are O;
• R 9 , R 10 and R 11 are independently hydrogen, Ci-C4alkyl, Ci-C4haloalkyl, Ci-C4thioalkyl or Ci-C4alkylthio Ci- C4alkyl;
• R 12 and R 13 are hydrogen; and n is 1 or 2.
• a 1 and A 3 are independently chloro, fluoro or
• B 1 and B 2 are C-H
• R 1 is CF 3 ;
• R 2 is hydrogen, methyl or CF 3 ;
• Z is O
• L is a bond or -NH-
• R 3 , R 4 , R 3' , R 4' , R 5 , R 6 , R 5 and R 6' are hydrogen; or
• a 1 and A 3 are independently chloro, fluoro or
• R 1 is CF 3 ;
• R 2 is hydrogen, methyl or CF 3 ;
• Z is O
• L is a bond or -NH-
• R 3 , R 4 , R 3' , R 4' , R 5 , R 6 , R 5 and R 6' are hydrogen; or
• Y is methyl, ethyl, propyl, 1 -methylethyl, butyl, 1 -methylpropyl, 2-methylpropyl or 1 , 1 -dimethylethyl.
• a 1 and A 3 are independently chloro, fluoro or
• B 1 and B 2 are C-H
• R 1 is CF 3 ;
• R 2 is hydrogen, methyl or CF 3 ;
• Z is O
• L is a bond or -NH-
• R 3 , R 4 , R 3' , R 4' , R 5 , R 6 , R 5 and R 6' are hydrogen; or
• Y is CF 3 , -CH 2 CF 3 , -CF 2 CF 3 , -CH 2 CH 2 CF 3 , -CH 2 CF 2 CF 3 , -CF 2 CF 2 CF 3 , - CH 2 CH 2 CH 2 CF 3 , -CH 2 CH 2 CF 2 CF 3 , -CH 2 CF 2 CF 2 CF 3 or -CF 2 CF 2 CF 2 CF 3 .
• a 1 and A 3 are independently chloro, fluoro or
• R 1 is CF 3 ;
• R 2 is hydrogen, methyl or CF 3 ;
• Z is O
• L is a bond or -NH-
• R 3 , R 4 , R 3' , R 4' , R 5 , R 6 , R 5 and R 6' are hydrogen; or
• Y is CF 3 , -CH 2 CF 3 , -CF 2 CF 3 , -CH 2 CH 2 CF 3 , -CH 2 CF 2 CF 3 , -CF 2 CF 2 CF 3 , - CH 2 CH 2 CH 2 CF 3 , -CH 2 CH 2 CF 2 CF 3 , -CH 2 CF 2 CF 2 CF 3 or -CF 2 CF 2 CF 2 CF 3 .
• a 1 and A 3 are independently chloro, fluoro or CF 3 ;
• B 1 and B 2 are C-H
• R 1 is CF 3 ;
• R 2 is hydrogen, methyl or CF 3 ;
• Z is O
• L is a bond or -NH-
• R 3 , R 4 , R 3' , R 4' , R 5 , R 6 , R 5 and R 6' are hydrogen; or
• Y is Y-l wherein W is O; and R 9 and R 10 are independently hydrogen, - CH 2 CH 2 SH, -CH 2 CH 2 SCH 3 or -CH 2 CH 2 SCF 3 .
• a 1 and A 3 are independently chloro, fluoro or CF 3 ;
• B 1 and B 2 are C-H
• R 1 is CF 3 ;
• R 2 is hydrogen, methyl or CF 3 ;
• Z is O
• L is a bond or -NH-
• R 3 , R 4 , R 3' , R 4' , R 5 , R 6 , R 5 and R 6' are hydrogen; or
• Y is Y-l wherein W is O; and R 9 and R 10 are independently hydrogen, - CH 2 CH 2 SH, -CH 2 CH 2 SCH 3 or -CH 2 CH 2 SCF 3 .
• a 1 and A 3 are independently chloro, fluoro or CF 3 ;
• B 1 and B 2 are C-H
• R 1 is CF 3 ;
• R 2 is hydrogen, methyl or CF 3 ;
• Z is O
• L is a bond or -NH-
• R 3 , R 4 , R 3' , R 4' , R 5 , R 6 , R 5 and R 6' are hydrogen; or
• Y is Y-4, wherein W and Wi are O; R 9 and R 10 are independently hydrogen or -CH 2 CF 3 ; R 12 and R 13 are hydrogen; and n is 1.
• a 1 and A 3 are independently chloro, fluoro or CF 3 ;
• R 1 is CF 3 ;
• R 2 is hydrogen, methyl or CF 3 ;
• Z is O
• L is a bond or -NH-
• R 3 , R 4 , R 3' , R 4' , R 5 , R 6 , R 5 and R 6' are hydrogen; or
• Y is Y-4, wherein W and Wi are O; R 9 and R 10 are independently hydrogen or -CH 2 CF 3 ; R 12 and R 13 are hydrogen; and n is 1.
• the invention provides parasiticidal and pesticidal compounds of formula (IC):
• Ri is alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl;
• a 1 and A 3 are independently hydrogen, halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl or haloalkynyl;
• B 1 and B 2 are independently N or C-X;
• R 2 is hydrogen, halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl or
• R 3 , R 4 , R 5 , R 6 , R 5 and R 6' are each independently hydrogen, halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl or haloalkynyl; or
• R 7 and R 8 are independently hydrogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, aryl, heteroaryl, heterocyclyl, thioalkyl, thiohaloalkyl, alkylthioalkyl, hydroxyalkyl or alkoxyalkyl;
• Y is hydrogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, alkylcycloalkyl, cycloalkylalkyl, aryl, heterocyclyl or heteroaryl each of which is unsubstituted or substituted with one or more of halogen, hydroxy, amino, alkyl- or di(alkyl)amino, alkyl, cycloalkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, R 7 S(0)-, R 7 S(0) 2 -, R 7 C(0)-, R 7 R 8 NC(0)-, R 7 OC(0)-, R 7 C(0)0-, R 7 C(0)NR 8 -, -CN or -N0
• each R 9 , R 10 are independently hydrogen, alkyl, haloalkyl, thioalkyl, alkylthioalkyl, hydroxyalkyl, alkoxylakyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, aryl, heteroaryl, heterocyclyl, R 7 S(0)-, R 7 S(0) 2 -, R 7 C(0)-, R 7 R 8 NC(0)-, R 7 OC(0)-, R 7 C(0)0-, R 7 C(0)NR 8 -;
• each R 11 is independently hydrogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, amino, alkylamino,
• haloalkylamino dialkylamino, dihaloalkylamino, hydroxyalkyl, alkoxyalkyl, thioalkyl or alkylthioalkyl;
• each R 12 and R 13 is independently hydrogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, amino, alkylamino, haloalkylamino, dialkylamino, dihaloalkylamino, hydroxyalkyl, alkoxyalkyl, thioalkyl or alkylthioalkyl; or
• W, Wi and Z are independently O, S or NR 7 ;
• L is a direct bond, -CR 3 R 4 -, -NR 8 - or -0-;
• n 1, 2, 3 or 4;
• n 0, 1 or 2.
• R 1 is alkyl or haloalkyl. In another embodiment, R 1 is C 1 -C 4 alkyl or Ci-C 4 haloalkyl. In another embodiment, R 1 is CF 3 .
• a 1 and A 3 are independently halogen, alkyl or haloalkyl. In an embodiment, A 1 and A 3 are independently halogen, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl.
• a 1 and A 3 are independently halogen, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl; and R 1 is C 1 -C 4 alkyl or Ci-C 4 haloalkyl.
• a 1 and A 3 are independently chloro, fluoro or CF 3 ; and R 1 is CF 3 .
• a 1 and A 3 are independently halogen, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl; B 1 and B 2 are C-H; and R 1 is C 1 -C 4 alkyl or Ci-C 4 haloalkyl.
• a 1 and A 3 are independently chloro, fluoro or CF 3 ; B 1 and B 2 are C-H; and R 1 is CF 3 .
• a 1 and A 3 are independently chloro, fluoro or CF 3 ;
• R 1 is CF 3 .
• R 2 is hydrogen, halogen, alkyl or haloalkyl. In still another embodiment, R 2 is hydrogen, halogen, C 1 -C 4 alkyl or Ci-C 4 haloalkyl. In another embodiment, R 2 is methyl or CF 3 .
• a 1 and A 3 are independently chloro, fluoro or CF 3; R 1 is CF 3 ; and R 2 is hydrogen, methyl or CF 3 .
• Y is alkyl, haloalkyl, alkenyl,
• haloalkenyl, alkynyl or haloalkynyl each of which is unsubstituted or substituted with one or more of hydroxy, amino, alkyl- or di(alkyl)amino, alkyl, cycloalkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, R?S(0)-, R 7 S(0) 2 -, R 7 C(0)-, R 7 R 8 NC(0)-, R 7 OC(0)-, R 7 C(0)0-, R 7 C(0)NR 8 -, -CN or -N0 2 .
• Y is Ci-C 6 alkyl or Ci-C 6 haloalkyl. In still another embodiment, Y is methyl, ethyl, propyl, 1 -methylethyl, butyl, 1 -methylpropyl, 2- methylpropyl or 1 , 1 -dimethylethyl.
• Y is CF 3 , -CH 2 CF 3 , -CF 2 CF 3 , -
• Y is Y-1, Y-2, Y-3, Y-4, Y-5, Y-6, Y-7, Y-8, Y-9, Y- 10, Y-11, Y-12 or Y-13.
• Y is Y-1, Y-4, Y-5, Y-6.
• Y is Y is Y-2, Y-3, Y-7, Y-8 or Y-9.
• Y is Y- 10, Y- 11 , Y- 12 or Y- 13.
• Y is Y-1, Y-4, Y-5 or Y-6, wherein W and Wi are 0; R 9 , R 10 and R 11 are independently hydrogen, alkyl, haloalkyl, thioalkyl or
• alkylthioalkyl R 12 and R 13 are hydrogen; and n is 1 or 2.
• Y is Y-2, Y-3, Y-7, Y-8 or Y-9, wherein W and Wi are O; R 9 , R 10 and R 11 are independently hydrogen, alkyl, haloalkyl, thioalkyl or alkylthioalkyl; R 12 and R 13 are hydrogen; and n is 1 or 2.
• Y is Y-1 wherein W is O; and R 9 and R 10 are independently hydrogen, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 thioalkyl or Ci- C 4 alkylthioalkyl.
• Y is Y-1 wherein W is O; and R 9 and R 10 are independently hydrogen, -CH 2 CH 2 SH, -CH 2 CH 2 SCH 3 or -CH 2 CH 2 SCF 3 .
• Y is Y-4, wherein W and Wi are O; R 9 and R 10 are independently hydrogen, Ci-C 4 alkyl or Ci-C 4 haloalkyl; R 12 and R 13 are hydrogen; and n is 1 or 2.
• Y is Y-4, wherein W and Wi are O; R 9 and R 10 are independently hydrogen or Ci-C 4 haloalkyl; R 12 and R 13 are hydrogen; and n is 1.
• Y is Y-4, wherein W and Wi are O; R 9 and R 10 are independently hydrogen or -CH 2 CF 3 ; R 12 and R 13 are hydrogen; and n is 1.
• a 1 and A 3 are independently halogen, alkyl or haloalkyl
• B 1 and B 2 are C-H
• R 1 is alkyl or haloalkyl
• R 2 is hydrogen, halogen, alkyl or haloalkyl
• Z is O
• L is a bond or -NR 7 -;
• R 3 , R 4 , R 5 , R 6 , R 5 and R 6' are each independently hydrogen, halogen, alkyl or haloalkyl; or
• a 1 and A 3 are independently halogen, alkyl or haloalkyl
• R 1 is alkyl or haloalkyl
• R 2 is hydrogen, halogen, alkyl or haloalkyl
• Z is O
• L is a bond or -NR 7 -;
• R 3 , R 4 , R 5 , R 6 , R 5 and R 6' are each independently hydrogen, halogen, alkyl or haloalkyl; or
• a 1 and A 3 are independently halogen, alkyl or haloalkyl
• B 1 and B 2 are C-H
• R 1 is alkyl or haloalkyl
• R 2 is hydrogen, halogen, alkyl or haloalkyl
• Z is O; L is a bond or -NR 7 -;
• R 3 , R 4 , R 5 , R 6 , R 5 and R 6" are each independently hydrogen, halogen, alkyl or haloalkyl; or
• Y is Y-l, Y-4, Y-5 or Y-6, in which W and Wi are O, R 9 , R 10 and R 11 are independently hydrogen, alkyl, haloalkyl, thioalkyl or alkylthioalkyl; R 12 and R 13 are hydrogen; and n is 1 or 2.
• a 1 and A 3 are independently halogen, alkyl or haloalkyl
• R 1 is alkyl or haloalkyl
• R 2 is hydrogen, halogen, alkyl or haloalkyl
• Z is O
• L is a bond or -NR 7 -;
• R 3 , R 4 , R 5 , R 6 , R 5 and R 6" are each independently hydrogen, halogen, alkyl or haloalkyl; or
• Y is Y-l, Y-4, Y-5 or Y-6, in which W and Wi are O, R 9 , R 10 and R 11 are independently hydrogen, alkyl, haloalkyl, thioalkyl or alkylthioalkyl; R 12 and R 13 are hydrogen; and n is 1 or 2.
• a 1 and A 3 are independently halogen, alkyl or haloalkyl
• B 1 and B 2 are C-H
• R 1 is alkyl or haloalkyl
• R 2 is hydrogen, halogen, alkyl or haloalkyl
• Z is O
• L is a bond or -NR 7 -;
• R 3 , R 4 , R 5 , R 6 , R 5 and R 6" are each independently hydrogen, halogen, alkyl or haloalkyl; or
• Y is Y is Y-2, Y-3, Y-7, Y-8 or Y-9, in which W and Wi are O;
• R 9 , R 10 and R 11 are independently hydrogen, alkyl, haloalkyl, thioalkyl or alkylthioalkyl;
• R 12 and R 13 are hydrogen; and
• n is 1 or 2.
• a 1 and A 3 are independently halogen, alkyl or haloalkyl
• R 1 is alkyl or haloalkyl
• R 2 is hydrogen, halogen, alkyl or haloalkyl
• Z is O
• L is a bond or -NR 7 -;
• R 3 , R 4 , R 5 , R 6 , R 5 and R 6" are each independently hydrogen, halogen, alkyl or haloalkyl; or
• Y is Y is Y-2, Y-3, Y-7, Y-8 or Y-9, in which W and Wi are O;
• R 9 , R 10 and R 11 are independently hydrogen, alkyl, haloalkyl, thioalkyl or alkylthioalkyl;
• R 12 and R 13 are hydrogen; and
• n is 1 or 2.
• a 1 and A 3 are independently halogen, C1-C4 alkyl or C1-C4 haloalkyl; B 1 and B 2 are C-H;
• R 1 is C1-C4 alkyl or Ci-C 4 haloalkyl
• R 2 is hydrogen, halogen, C1-C4 alkyl or Ci-C 4 haloalkyl
• Z is O
• L is a bond or -NR 7 -;
• R 3 , R 4 , R 5 , R 6 , R 5 and R 6 are each hydrogen or halogen; or
• Y is Ci-C 6 alkyl or Ci-C 6 haloalkyl.
• a 1 and A 3 are independently halogen
• R 1 is C1-C4 alkyl or Ci-C 4 haloalkyl
• R 2 is hydrogen, halogen, C1-C4 alkyl or Ci-C 4 haloalkyl
• Z is O
• L is a bond or -NR 7 -;
• R 3 , R 4 , R 5 , R 6 , R 5 and R 6 are each hydrogen or halogen; or
• Y is Ci-C 6 alkyl or Ci-C 6 haloalkyl.
• a 1 and A 3 are independently halogen, C1-C4 alkyl or Ci-C 4 haloalkyl;
• B 1 and B 2 are C-H;
• R 1 is C1-C4 alkyl or Ci-C 4 haloalkyl;
• R 2 is hydrogen, halogen, C1-C4 alkyl or Ci-C 4 haloalkyl
• Z is O
• L is a bond or -NR 7 -;
• R 3 , R 4 , R 5 , R 6 , R 5 and R 6 are each hydrogen or halogen; or
• Y is Y-l, Y-4, Y-5 or Y-6 in which W and Wi are O;
• R 9 , R 10 and R 11 are independently hydrogen, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 thioalkyl or Ci-C 4 alkylthio Ci- C 4 alkyl;
• R 12 and R 13 are hydrogen; and n is 1 or 2.
• a 1 and A 3 are independently halogen, C1-C4 alkyl or Ci-C 4 haloalkyl;
• R 1 is C1-C4 alkyl or Ci-C 4 haloalkyl
• R 2 is hydrogen, halogen, C1-C4 alkyl or Ci-C 4 haloalkyl
• Z is O
• L is a bond or -NR 7 -;
• R 3 , R 4 , R 5 , R 6 , R 5 and R 6 are each hydrogen or halogen; or
• Y is Y-l, Y-4, Y-5 or Y-6 in which W and Wi are O;
• R 9 , R 10 and R 11 are independently hydrogen, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 thioalkyl or Ci-C 4 alkylthio Ci- C 4 alkyl;
• R 12 and R 13 are hydrogen; and
• n is 1 or 2.
• a 1 and A 3 are independently halogen, Ci- C 4 alkyl or Ci-C 4 haloalkyl;
• B 1 and B 2 are C-H
• R 1 is C1-C4 alkyl or Ci-C 4 haloalkyl
• R 2 is hydrogen, halogen, C1-C4 alkyl or Ci-C 4 haloalkyl
• Z is O
• L is a bond or -NR 7 -;
• each R 3 , R 4 , R 5 , R 6 , R 5 and R 6 are each hydrogen or halogen;
• Y is Y-2, Y-3, Y-7, Y-8 or Y-9, wherein W and Wi are O;
• R 9 , R 10 and R 11 are independently hydrogen, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 thioalkyl or Ci-C 4 alkylthio Ci- C 4 alkyl;
• R 12 and R 13 are hydrogen; and n is 1 or 2.
• a 1 and A 3 are independently halogen, Ci- C 4 alkyl or C1-C4 haloalkyl;
• R 1 is C1-C4 alkyl or Ci-C 4 haloalkyl
• R 2 is hydrogen, halogen, C1-C4 alkyl or Ci-C 4 haloalkyl
• Z is O
• L is a bond or -NR 7 -;
• each R 3 , R 4 , R 5 , R 6 , R 5 and R 6 are each hydrogen or halogen;
• a 1 and A 3 are independently chloro, fluoro or CF 3 ;
• B 1 and B 2 are C-H
• R 1 is CF 3 ;
• R 2 is hydrogen, methyl or CF 3 ;
• Z is O
• L is a bond or -NH-
• R 3 , R 4 , R 5 , R 6 , R 5 and R 6' are each hydrogen; or
• Y is methyl, ethyl, propyl, 1 -methylethyl, butyl, 1 -methylpropyl, 2-methylpropyl or 1,1-dimethylethyl.
• a 1 and A 3 are independently chloro, fluoro or
• R 1 is CF 3 ;
• R 2 is hydrogen, methyl or CF 3 ;
• Z is O
• L is a bond or -NH-
• R 3 , R 4 , R 5 , R 6 , R 5 and R 6' are each hydrogen; or
• Y is methyl, ethyl, propyl, 1 -methylethyl, butyl, 1 -methylpropyl, 2-methylpropyl or 1 , 1 -dimethylethyl.
• a 1 and A 3 are independently chloro, fluoro or
• B 1 and B 2 are C-H
• R 1 is CF 3 ;
• R 2 is hydrogen, methyl or CF 3 ;
• Z is O
• L is a bond or -NH-
• R 3 , R 4 , R 5 , R 6 , R 5 and R 6' are each hydrogen; or
• Y is CF 3 , -CH 2 CF 3 , -CF 2 CF 3 , -CH 2 CH 2 CF 3 , -CH 2 CF 2 CF 3 , -CF 2 CF 2 CF 3 , - CH 2 CH 2 CH 2 CF 3 , -CH 2 CH 2 CF 2 CF 3 , -CH 2 CF 2 CF 2 CF 3 or -CF 2 CF 2 CF 2 CF 3 .
• a 1 and A 3 are independently chloro, fluoro or
• R 1 is CF 3 ;
• R 2 is hydrogen, methyl or CF 3 ;
• Z is O
• L is a bond or -NH-
• R 3 , R 4 , R 5 , R 6 , R 5 and R 6' are each hydrogen; or
• Y is CF 3 , -CH 2 CF 3 , -CF 2 CF 3 , -CH 2 CH 2 CF 3 , -CH 2 CF 2 CF 3 , -CF 2 CF 2 CF 3 , - CH 2 CH 2 CH 2 CF 3 , -CH 2 CH 2 CF 2 CF 3 , -CH 2 CF 2 CF 2 CF 3 or -CF 2 CF 2 CF 2 CF 3 .

Landscapes

• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Life Sciences & Earth Sciences (AREA)
• Health & Medical Sciences (AREA)
• General Health & Medical Sciences (AREA)
• Veterinary Medicine (AREA)
• Environmental Sciences (AREA)
• Dentistry (AREA)
• Zoology (AREA)
• Wood Science & Technology (AREA)
• Agronomy & Crop Science (AREA)
• Pest Control & Pesticides (AREA)
• Plant Pathology (AREA)
• Engineering & Computer Science (AREA)
• Medicinal Chemistry (AREA)
• Pharmacology & Pharmacy (AREA)
• Animal Behavior & Ethology (AREA)
• Public Health (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
• General Chemical & Material Sciences (AREA)
• Tropical Medicine & Parasitology (AREA)
• Dispersion Chemistry (AREA)
• Toxicology (AREA)
• Epidemiology (AREA)
• Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)
• Plural Heterocyclic Compounds (AREA)
• Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Priority Applications (18)

Applications Claiming Priority (2)

Publications (1)

Family

ID=51987452

Family Applications (1)

Country Status (22)

Cited By (11)

Families Citing this family (8)

Citations (134)

Family Cites Families (8)

• 2014
  • 2014-10-30 WO PCT/US2014/063074 patent/WO2015066277A1/en not_active Ceased
  • 2014-10-30 NZ NZ719916A patent/NZ719916A/en not_active IP Right Cessation
  • 2014-10-30 EP EP20169448.6A patent/EP3733664A1/en active Pending
  • 2014-10-30 SG SG11201603430XA patent/SG11201603430XA/en unknown
  • 2014-10-30 EP EP14803270.9A patent/EP3063144B1/en active Active
  • 2014-10-30 JP JP2016552230A patent/JP6484641B2/ja active Active
  • 2014-10-30 KR KR1020167014400A patent/KR102341193B1/ko not_active Expired - Fee Related
  • 2014-10-30 CA CA2929234A patent/CA2929234C/en active Active
  • 2014-10-30 DK DK14803270.9T patent/DK3063144T3/da active
  • 2014-10-30 AP AP2016009184A patent/AP2016009184A0/en unknown
  • 2014-10-30 ES ES14803270T patent/ES2905848T3/es active Active
  • 2014-10-30 PL PL14803270T patent/PL3063144T3/pl unknown
  • 2014-10-30 EA EA201690910A patent/EA030935B1/ru unknown
  • 2014-10-30 US US14/528,172 patent/US9447084B2/en active Active
  • 2014-10-30 CN CN201480071748.9A patent/CN105873925B/zh active Active
  • 2014-10-30 MX MX2016005693A patent/MX361516B/es active IP Right Grant
  • 2014-10-30 AU AU2014342241A patent/AU2014342241B2/en not_active Ceased
  • 2014-10-30 PT PT14803270T patent/PT3063144T/pt unknown
  • 2014-10-31 TW TW103137923A patent/TWI658040B/zh not_active IP Right Cessation
  • 2014-10-31 UY UY0001035810A patent/UY35810A/es not_active Application Discontinuation
  • 2014-11-03 AR ARP140104102A patent/AR098266A1/es active IP Right Grant
• 2016
  • 2016-04-29 CL CL2016001043A patent/CL2016001043A1/es unknown
  • 2016-05-01 IL IL245384A patent/IL245384B/en active IP Right Grant
• 2017
  • 2017-11-27 AU AU2017268490A patent/AU2017268490B2/en not_active Ceased
• 2019
  • 2019-02-18 JP JP2019026311A patent/JP6817354B2/ja active Active

Patent Citations (166)