• 专利附录
  • 专利说明
  • 权利要求
  • 类似技术
  • 同族专利
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    • 专利摘要:
    The present invention relates to animal and human treatment, control, and arthropod groups of animals and humans by administering or applying the 1,4-diaryl-3-fluoro-2-butene compounds of Formula 1 to animals, humans or their environment A method and composition for prevention and protection from invasion and infection by a living body.
    公开号:KR19990068104A
    申请号:KR1019990002207
    申请日:1999-01-25
    公开日:1999-08-25
    发明作者:도셔메리엘러스；히니캐쓸린；슁해머커트앨런
    申请人:윌리암 에이취 캘넌, 에곤 이 버그；아메리칸사이아나미드컴파니；
    IPC主号:
    专利说明:

    1,4-DIARYL-3-FLUORO-2-BUTENE COMPOUNDS FOR Protecting Animals and Humans Against Attack and Invasion by Arthropod Parasites PROTECTING ANIMALS AND HUMANS AGAINST ATTACK AND INFESTATION BY ARTHROPOD PARASITES}
    The present invention relates to 1,4-diaryl-3-fluoro-2-butene compounds for protecting animals and humans against attack and invasion by arthropod parasites. Arthropods and Parasites Parasites cause hundreds of millions of dollars in economic losses each year on a global basis. In particular, flies, fleas, teeth, mosquitoes, horns, mites, ticks and parasites cause huge losses in the livestock and accompanying animal areas. Arthropod parasites are also harmful to humans and can mediate disease-causing organisms in humans and animals.
    Despite the repellents on the market today, damage still occurs to humans, livestock and accompanying animals. Therefore, the creation of new and more effective antiparasitic agents is an ongoing research challenge.
    Particular 1,4-diaryl-3-fluoro-2-butene compounds useful for controlling white flies are described in WO 97/16067. Certain fluoroolefin compounds useful as soil pesticides are described in WO94 / 06741. However, neither WO 97/16067 nor WO 94/06741 describe methods for protecting animals and humans from attack and invasion by arthropod parasites.
    US Pat. No. 5,248,834 generally describes certain fluoroolefin compounds that can be used to combat pests in many fields, including in the medical field. However, this patent does not describe the fluoroolefin compound in detail. In addition, this patent does not provide a method for preparing a fluoroolefin compound.
    GB 2,288,803-A describes certain fluoroolefin compounds that can be used to combat pests in many fields, including in the medical field. However, this patent application teaches that this has nothing to do with medical applications because it describes that fluoroolefin compounds are particularly useful as soil pesticides.
    It is therefore an object of the present invention to provide methods for the treatment and control of animals and humans, and for the prevention and protection from invasion and infection by arthropod parasites of animals and humans.
    It is also an object of the present invention to provide compositions for the treatment and control of animals and humans, and for the prevention and protection from invasion and infection by arthropod parasites of animals and humans.
    These and other objects of the present invention will become more apparent from the detailed description set forth below.
    The present invention relates to an animal and a human, comprising administering to or administering an insecticidal effective amount of the 1,4-diaryl-3-fluoro-2-butene compound of Formula 1 or an optical isomer thereof to the animal, human or their environment It provides a method for the control, prevention and protection from invasion and infection by arthropod parasites.
    Formula 1

    In the above formula,
    R is hydrogen or C 1 -C 4 alkyl,
    R 1 is C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or cyclopropyl, or R and R 1 are taken together with the carbon atom to which they are attached to form a cyclopropyl group;
    Ar is optionally up to 3 groups independently selected from halogen atoms, C 1 -C 4 alkyl groups, C 1 -C 4 haloalkyl groups, C 1 -C 4 alkoxy groups, or C 1 -C 4 haloalkoxy groups Substituted phenyl, or
    Optionally substituted with up to 3 groups independently selected from halogen atoms, C 1 -C 4 alkyl groups, C 1 -C 4 haloalkyl groups, C 1 -C 4 alkoxy groups, or C 1 -C 4 haloalkoxy groups 1- or 2-naphthyl;
    Ar 1 is 5 or less groups independently selected from halogen atoms, C 1 -C 4 alkyl groups, C 1 -C 4 haloalkyl groups, C 1 -C 4 alkoxy groups, or C 1 -C 4 haloalkoxy groups Optionally substituted phenoxyphenyl,
    Optionally substituted with up to 5 groups independently selected from halogen atoms, C 1 -C 4 alkyl groups, C 1 -C 4 haloalkyl groups, C 1 -C 4 alkoxy groups, or C 1 -C 4 haloalkoxy groups Phenyl,
    Optionally substituted with up to 5 groups independently selected from halogen atoms, C 1 -C 4 alkyl groups, C 1 -C 4 haloalkyl groups, C 1 -C 4 alkoxy groups, or C 1 -C 4 haloalkoxy groups Biphenyl,
    Optionally substituted with up to 5 groups independently selected from halogen atoms, C 1 -C 4 alkyl groups, C 1 -C 4 haloalkyl groups, C 1 -C 4 alkoxy groups, or C 1 -C 4 haloalkoxy groups Benzylphenyl, or
    Optionally substituted with up to 5 groups independently selected from halogen atoms, C 1 -C 4 alkyl groups, C 1 -C 4 haloalkyl groups, C 1 -C 4 alkoxy groups, or C 1 -C 4 haloalkoxy groups Benzoylphenyl,
    The arrangement of the groups ArCRR 1 -and -CH 2 Ar 1 around the double bond is mainly trans trans.
    The invention also provides compositions for control, prevention and protection from invasion and infection by arthropod parasites in animals and humans. The composition of the present invention comprises an arthropod effective amount of a compound of formula (1) with an agriculturally or pharmaceutically acceptable carrier. Advantageously, the 1,4-diaryl-3-fluoro-2-butene compounds of the present invention and compositions containing the same are described herein for invasion and infection by flies, fleas, teeth, mosquitoes, horns, mites and ticks. It has been found to be particularly useful in the execution of the.
    1,4-Diaryl-3-fluoro-2-butene compounds useful in the methods and compositions of the present invention have formula (1).
    Formula 1
    In the above formula,
    R, R 1 , Ar and Ar 1 are as described for Formula 1 above.
    Preferred compounds of formula 1 for use in the methods and compositions of the present invention are those wherein R is hydrogen and R 1 is isopropyl, trifluoromethyl or cyclopropyl, R and R 1 are methyl, and R and R 1 are attached Taken together with the resulting carbon atoms to form cyclopropyl groups;
    Ar is optionally up to 3 groups independently selected from halogen atoms, C 1 -C 4 alkyl groups, C 1 -C 4 haloalkyl groups, C 1 -C 4 alkoxy groups, or C 1 -C 4 haloalkoxy groups Substituted phenyl;
    Ar 1 is 5 or less groups independently selected from halogen atoms, C 1 -C 4 alkyl groups, C 1 -C 4 haloalkyl groups, C 1 -C 4 alkoxy groups, or C 1 -C 4 haloalkoxy groups Optionally substituted 3-phenoxyphenyl,
    Optionally substituted with up to 5 groups independently selected from halogen atoms, C 1 -C 4 alkyl groups, C 1 -C 4 haloalkyl groups, C 1 -C 4 alkoxy groups, or C 1 -C 4 haloalkoxy groups 3-biphenyl,
    Optionally substituted with up to 5 groups independently selected from halogen atoms, C 1 -C 4 alkyl groups, C 1 -C 4 haloalkyl groups, C 1 -C 4 alkoxy groups, or C 1 -C 4 haloalkoxy groups 3-benzylphenyl, or
    Optionally substituted with up to 5 groups independently selected from halogen atoms, C 1 -C 4 alkyl groups, C 1 -C 4 haloalkyl groups, C 1 -C 4 alkoxy groups, or C 1 -C 4 haloalkoxy groups 3-benzoylphenyl.
    More preferred compounds of formula 1
    R is hydrogen and R 1 is isopropyl, trifluoromethyl or cyclopropyl or R and R 1 are methyl or R and R 1 are taken together with the carbon atom to which they are attached to form a cyclopropyl group;
    Ar is optionally substituted with up to 3 groups independently selected from halogen atoms, C 1 -C 4 alkyl groups, C 1 -C 4 haloalkyl groups, C 1 -C 4 alkoxy groups or C 1 -C 4 haloalkoxy groups Phenyl;
    Ar 1 is optionally up to 5 groups independently selected from halogen atoms, C 1 -C 4 alkyl groups, C 1 -C 4 haloalkyl groups, C 1 -C 4 alkoxy groups or C 1 -C 4 haloalkoxy groups Substituted 3-phenoxyphenyl.
    Most preferred compounds of formula 1 for use in the present invention
    R is hydrogen and R 1 is isopropyl, trifluoromethyl or cyclopropyl or R and R 1 are taken together with the carbon atom to which they are attached to form a cyclopropyl group;
    Ar is 4-chlorophenyl, 4-fluorophenyl, 4- (trifluoromethoxy) phenyl or 4-ethoxyphenyl;
    Ar 1 is 4-fluoro-3-phenoxyphenyl, m- (p-fluorophenoxy) phenyl, 4-fluoro-3- (p-fluorophenoxy) phenyl or 3-phenoxyphenyl to be.
    1,4-Diaryl-3-fluoro-2-butene compounds which are particularly useful for the treatment, control, prevention and protection from invasion and infection by animal and human arthropod parasites include, among others, 1- (p- Chlorophenyl) -1- [2-fluoro-3- (4-fluoro-3-phenoxyphenyl) propenyl] cyclopropane, (Z)-;
    2,5,5,5-tetrafluoro-4- (p-fluorophenyl) -1- (m-phenoxyphenyl) -2-pentene, (Z)-;
    4- (p-chlorophenyl) -2-fluoro-1- (4-fluoro-3-phenoxyphenyl) -5-methyl-2-hexene, (Z)-;
    1- [1- (p-chlorophenyl) -3-fluoro-4- (4-fluoro-3-phenoxyphenyl) -2-butenyl] cyclopropane, (Z)-;
    1- {1- (p-chlorophenyl) -3-fluoro-4- [4-fluoro-3- (p-fluorophenoxy) phenyl] -2-butenyl} cyclopropane, (Z)- ; And
    1- [3-fluoro-4- (4-fluoro-3-phenoxyphenyl) -1- [- (trifluoromethoxy) phenyl] -2-butenyl} cyclopropane, (Z) -is Included.
    Dermatitis fly larvae and intranasal boats, mites, including those that cause fleas, ticks, teeth, mosquitoes, angulates, flies, chimneys, horseflies, muscoid flies, sheep mites, intestinal complications Animals including, but not limited to, chiggers and cattle, sheep, horses, deer, camels, pigs, goats, ferrets, mink, rabbits, amphibians, reptiles, fish, birds, poultry, dogs, and cats and humans It is useful for invasion and infection by arthropod parasites including, but not limited to, parasites, which are aspirated and dug in. The methods and compositions of the present invention are particularly useful for treating, controlling, preventing and protecting animals and humans from invasion and infection by flies, fleas, teeth, mosquitoes, horns, mites and ticks.
    The 1,4-diaryl-3-fluoro-2-butene compound may be used for the treatment of mesostig mata (e.g. poultry mite), amok prostigmata (e.g. Mite), Astigmata (e.g., propropt and sarcopite mite) and Cryptostigmata (e.g., beetle mite), and Acariformes, and ) Members of Acarina including members of Ixodoidea, Ixodidae (eg hard ticks) and Argasidae (eg soft ticks) It is effective against arthropod parasites of animals and humans from Suba Akari. The compounds are also Diptera (Simuliidae, Phlebotominae, Ceratopogonidae, Culcidae, Rhagionidae, Athericidae, Chlorophyll) Chloropidae, Sarcophagidae, Tabanidae, Muscidae, Hippoboscidae and Califoridae, Siphonaptera (Siphonaptera) ) Ctenocephalides, Echidnophaga, Pulex and Xenopsylla fleas), Mallogaga (genus Bovicola, Trichodextes) (Including birds of Trichodectes and Damilina), Anoplura (including aspiration of genus Haematopinus, Linognathus and Solenopotes) and hemi To arthropod parasites of animals and humans of the Insect River, including members of the throat of Haemiptera It is effective.
    The methods and compositions of the present invention also include river Trematoda comprising a member of the neck Digenea (eg, Fasciola Hepatica); River Cotyloda (eg, Diphyllobothrium spp. And Spirometra spp.); River Eucestoda (eg, Moniezia spp., Talnia spp., And Echinococcus spp.); And throat Rhabditida, Strongylida (e.g., Haemonchus spp., Ostertagia ssp., Couperia spp., And ancyclostoma (Ancyclostoma) spp.), Oxyurida (e.g., Oxyuris spp.), Ascaridida (e.g., Toxacara spp.), Spiruida (Spirurida) (e.g., Dracunculus spp., Thelazia spp., Onchocera spp., And Dirofilaria spp.) And Enopplida It may be useful for parasite parasites from the river Nematoda, including members of (e.g., Trichuris spp.).
    Compounds of formula (1) may be parasitic, for example benzimidazole, piperazine, levamizole, pylantel, praziquantel and the like; Endectosides such as avermectin, milbemycin and the like; External repellents such as arylpyrrole including chlorfenapyr, organophosphate, carbamate, fipronil, including gambutyric acid inhibitors, pyrethroids, spinosads, imidacloprids and the like; Insect growth regulators such as pyriproxyfen, sirromamine, and the like; Chitin synthesis inhibitors, such as flufenoxuron, can be used in combination or in combination with one or more other parasitic compounds including but not limited to benzoylurea.
    Compounds of formula (I) are also conventional synergists such as piperonyl butoxide, N-octyl bicycloheptene dicarboximide, to enhance potency, broaden the spectrum, and provide convenient methods for parasite control. It can be used in combination or in combination with dipropyl pyridine-2,5-dicarboxylate and 1,5a, 6,9,9a, 9b-hexahydro-4a (4H) -dibenzofurancarboxaldehyde.
    Compounds of formula (I) are pore-on, spot-on, spray, dip, bag-rubber, wettable powder, dust, emulsifiable concentrate, aqueous flow, shampoo on animal or human skin, leather, hair, feathers or hair It can be applied topically as a paste, foam, cream, solution, suspension or gel. These compositions generally contain about 0.1 ppm to 700,000 ppm of active compound. The compounds can also be presented in the form of solid matrices such as tacks, collars or medals.
    The compounds of formula 1 may also be mixed into the feed when prepared as solutions, pastes, gels, tablets, pills, potions or as feed premixes and administered orally, intragastrically or in rumen. Such administration is particularly useful for the regulation of intestinal and intraluminal hypothermia and the prevention of parasite growth in feces and urine of treated animals and humans. In addition, the compounds of formula 1 may be parenterally administered to animals and humans.
    The compounds of formula 1 may also be applied to the environment in which animals and humans reside as sprays, powders, baits, solid matrices, solutions, wettable powders, emulsifiable concentrates or fumigants. Such environments may include, but are not limited to, homes, yards, barns, barns, kennels, poultry houses, feeding lots, stalls, barns, offices, workshops, food manufacturing facilities, milking parlors, fish farms, bird kennels, zoos, and the like. Do not.
    The amount of active compound administered or applied to an animal, human, or environment thereof will vary depending upon the particular compound, target pest, method of application or administration, and particular host to be treated. Those skilled in the art can easily determine what the pest effective amount is without making inappropriate experiments.
    1,4-Diaryl-3-fluoro-2-butene compounds useful in the methods and compositions of the present invention and methods for their preparation are described in GB 2,288,803-A; WO 94/06741; WO 97/16067; And co-pending June 19, 1997, US patent application Ser. No. 08 / 879,918.
    In order to further facilitate the understanding of the present invention, the following examples are presented primarily for the purpose of describing more specific details. The scope of the invention should not be considered as being limited by the examples, but encompasses the entirety of the subject matter defined in the claims.
    Example 1
    Evaluation of Test Compounds for Adult Cat Fleas, Ctenocephalides felis
    This test is designed to assess the contact activity of test compounds against adult cat fleas. Test compounds are dissolved in 100% acetone at 300, 100, 10 and 1 ppm. 100 μl of each of these dilutions is added to the bottom of a 20 ml glass scintillation vial with a pipette. The vial is dried for 15 minutes under a fume hood. The bottom of the vial is measured 4.909 cm 2 . The amount of test compound applied by each dilution is 6.2, 2.0, 0.2 and 0.02 μg / cm 2, respectively. To fix the newly emerged adult cat fleas, anesthetize with CO 2 and count with a flash vial with forceps. Five fleas are placed on each vial. This test is repeated 2 to 3 times to be 10-15 fleas / speed / compound. The lethality reading takes 4 to 24 hours after placing the flea on the vial. Fleas that do not move during disturbance are considered dead. Percent mortality is then calculated for each treatment.
    The data obtained are reported in Table 2. Compound numbers are assigned to compounds used in the evaluation of the invention and are identified by name. The data in Table 2 is recorded by compound number.
    Evaluated compounds Compound numberEvaluated compounds One1- (p-chlorophenyl) -1- [2-fluoro-3- (4-fluoro-3-phenoxyphenyl) propenyl] cyclopropane, (Z)- 22,5,5,5-tetrafluoro-4- (p-fluorophenyl) -1- (m-phenoxyphenyl) -2-pentene, (Z)- 34- (p-chlorophenyl) -2-fluoro-5-methyl-1- (m-phenoxyphenyl) -2-hexene, (Z)- 44- (p-chlorophenyl) -2-fluoro-1- (4-fluoro-3-phenoxyphenyl) -5-methyl-2-hexene, (Z)-and (E)-, (8: One) 52-fluoro-4- (p-fluorophenyl) -5-methyl-1- (m-phenoxyphenyl) -2-hexene, (Z)- 64- (p-ethoxyphenyl) -2-fluoro-5-methyl-1- (m-phenoxyphenyl) -2-hexene, (Z)- 71- [1- (p-chlorophenyl) -3-fluoro-4- (4-fluoro-3-phenoxyphenyl) -2-butenyl] cyclopropane, (Z)- 81- {1- (p-chlorophenyl) -3-fluoro-4- [m- (p-fluorophenoxy) phenyl] -2-butenyl} cyclopropane, (Z)- 91- {1- (p-chlorophenyl) -3-fluoro-4- [4-fluoro-3- (p-fluorophenoxy) phenyl] -2-butenyl} cyclopropane, (Z)- 101- {3-fluoro-4- (4-fluoro-3-phenoxyphenyl) -1- [- (trifluoromethoxy) phenyl] -2-butenyl} cyclopropane, (Z)-
    Evaluation of Test Compounds for Ctenosepalides Felis (Cat Fleas) Compound numberDose (㎍ / cm 2 )4 hours% mortality rate24 hour% lethality One6.201001002.00401000.2040600.022050 26.20801002.00301000.20060 36.200102.0000 46.200902.000400.2000 56.200202.0000 66.200272.000200.2000 76.20601002.0040800.2020200.0200 86.200602.0000 96.2047952.0026470.200210.0206 106.201001002.00601000.2030700.02010
    Example 2
    Evaluation of Test Compounds for Adult Horn Fly, Haematobia irritans (pyrethroid-sensitive)
    This test is performed using 9 cm Whatman No. 1 filter paper placed in a 100 x 20 mm disposable plastic Petri dish. The test dose is expressed as μg of test substance per cm 2 of filter paper.
    1) A solution of the test compound in acetone is prepared such that 800 or 1000 μl contains the amount necessary to obtain the desired volume ratio.
    2) Pipette 800 or 100 μl of the test solution into the filter paper.
    3) The filter paper is dried under a fume hood.
    4) On drying, place filter paper on top of Petri dishes. The dish is generally held for about 24 hours before the test organics are added.
    5) Two to five day old horn flies (pyrethroid-sensitive) with two or more blood foods are used for the analysis. Collect flies in small vials from us. The vial is then chilled in the freezer for about 4 minutes to fix the fly. The fixed flies are spread on the Petri dish bottom with 12 to 25 flies per dish, then the dish is closed and turned over.
    6) As soon as flies move (about 5 minutes), they are examined to detect dead or damaged flies. This number is subtracted from the total number of flies in the dish.
    7) The petri dishes are kept at room temperature and irradiated at desired time intervals, which can be from 10 minutes to 6 hours.
    8) Record all dead flies at each survey time. The flies may still move but are considered dead if they cannot walk.
    9) Each test has a control dish containing filter paper treated only with acetone.
    10) Percent mortality at a specific time is calculated using the following formula.
    (Number of dead flies-dead after 5 minutes) / (Total number of flies-dead after 5 minutes) x 100
    Percent lethality is then corrected for control lethality using the Abbott formula.
    Data for pyrethroid-sensitive horn flies are reported in Table 3. The compound evaluated is reported by the compound number given in Example 1.
    Evaluation of Test Compounds for Adult Pyrethroid-Sensitive Horn Fly (Hematovia iritans) Compound numberDose (㎍ / cm 2 )6 hours% lethality One20.0010010.00955.00532.50161.2530.625One0.31250 710.01005.00982.50801.25150.62520.31250
    Example 3
    Evaluation of Test Compounds for Adult Housefly, Musca domestica
    This test is designed to assess the activity of the test compound against housefly. Test compounds are dissolved in 100% acetone at 300, 100 and 10 ppm. 100 μl of each of these dilutions is added to the bottom of a 20 ml glass scintillation vial with a pipette. The vial is dried for 15 minutes under a fume hood. The vial is then faced and 250 μl of each dilution is applied to the side of the vial. Place the vial into the rolling machine and roll under the hood until the acetone evaporates completely and coat the side of the vial. The bottom of the vial is measured at 4.909 cm 2 and the side is measured at 4.5 height x 8.8 circumference so that the total coating area of the flash vial is 44.51 cm 2 . The amount of test compound applied by each dilution is 2.36, 0.79 and 0.079 μg / cm 2, respectively. Two to three repetitions of untreated vials are included in all tests. The 5-7 day old adult housefly is chilled in the freezer for 5 minutes and placed on a sorting platform that provides a constant CO 2 stream to keep the fly stationary.
    Five flies are counted with each flash vial with forceps. Close the top of the vial with a sheet cotton plug sufficient to contain the fly. This test is repeated 2 to 4 times to give 10-20 flies / speed / compound. The lethality reading takes 1 to 4 hours after placing the flea on the vial. Flies that cannot stand during disturbance are considered dead. Percent mortality is then counted for each treatment.
    The data obtained are reported in Table 4. The compound evaluated is reported by the number given in Example 1.
    Evaluation of Test Compounds for Musca Domestica Compound numberDose (㎍ / cm 2 )1 hour% mortality rate4 hours% mortality 92.36015800.79020650.079050 102.3605950.7900500.079545
    The present invention provides methods and compositions for animal and human treatment, control, and prevention and protection from invasion and infection by arthropod parasites in animals and humans.
    权利要求:
    Claims (20)
    [1" claim-type="Currently amended] For control, prevention and protection from invasion and infection by arthropods of animals and humans, including administering or including an insecticidal effective amount of a compound of Formula 1 or an optical isomer thereof to an animal, human or their environment Treatment method.
    Formula 1

    In the above formula,
    R is hydrogen or C 1 -C 4 alkyl,
    R 1 is C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or cyclopropyl, or R and R 1 are taken together with the carbon atom to which they are attached to form a cyclopropyl group;
    Ar is optionally up to 3 groups independently selected from halogen atoms, C 1 -C 4 alkyl groups, C 1 -C 4 haloalkyl groups, C 1 -C 4 alkoxy groups, or C 1 -C 4 haloalkoxy groups Substituted phenyl, or
    Optionally substituted with up to 3 groups independently selected from halogen atoms, C 1 -C 4 alkyl groups, C 1 -C 4 haloalkyl groups, C 1 -C 4 alkoxy groups, or C 1 -C 4 haloalkoxy groups 1- or 2-naphthyl;
    Ar 1 is 5 or less groups independently selected from halogen atoms, C 1 -C 4 alkyl groups, C 1 -C 4 haloalkyl groups, C 1 -C 4 alkoxy groups, or C 1 -C 4 haloalkoxy groups Optionally substituted phenoxyphenyl,
    Optionally substituted with up to 5 groups independently selected from halogen atoms, C 1 -C 4 alkyl groups, C 1 -C 4 haloalkyl groups, C 1 -C 4 alkoxy groups, or C 1 -C 4 haloalkoxy groups Phenyl,
    Optionally substituted with up to 5 groups independently selected from halogen atoms, C 1 -C 4 alkyl groups, C 1 -C 4 haloalkyl groups, C 1 -C 4 alkoxy groups, or C 1 -C 4 haloalkoxy groups Biphenyl,
    Optionally substituted with up to 5 groups independently selected from halogen atoms, C 1 -C 4 alkyl groups, C 1 -C 4 haloalkyl groups, C 1 -C 4 alkoxy groups, or C 1 -C 4 haloalkoxy groups Benzylphenyl, or
    Optionally substituted with up to 5 groups independently selected from halogen atoms, C 1 -C 4 alkyl groups, C 1 -C 4 haloalkyl groups, C 1 -C 4 alkoxy groups, or C 1 -C 4 haloalkoxy groups Benzoylphenyl,
    The arrangement of the groups ArCRR 1 -and -CH 2 Ar 1 around the double bond is mainly trans trans.
    [2" claim-type="Currently amended] The compound of claim 1, wherein R is hydrogen and R 1 is isopropyl, trifluoromethyl or cyclopropyl, R and R 1 are methyl, or R and R 1 are taken together with the carbon atom to which they are attached to form a cyclopropyl group. Form;
    Ar is optionally substituted with up to 3 groups independently selected from halogen atoms, C 1 -C 4 alkyl groups, C 1 -C 4 haloalkyl groups, C 1 -C 4 alkoxy groups or C 1 -C 4 haloalkoxy groups Phenyl;
    Ar 1 is up to 5 groups independently selected from halogen atoms, C 1 -C 4 alkyl groups, C 1 -C 4 haloalkyl groups, C 1 -C 4 alkoxy groups, or C 1 -C 4 haloalkoxy groups Optionally substituted 3-phenoxyphenyl,
    Optionally substituted with up to 5 groups independently selected from halogen atoms, C 1 -C 4 alkyl groups, C 1 -C 4 haloalkyl groups, C 1 -C 4 alkoxy groups, or C 1 -C 4 haloalkoxy groups 3-biphenyl,
    Optionally substituted with up to 5 groups independently selected from halogen atoms, C 1 -C 4 alkyl groups, C 1 -C 4 haloalkyl groups, C 1 -C 4 alkoxy groups, or C 1 -C 4 haloalkoxy groups 3-benzylphenyl, or
    Optionally substituted with up to 5 groups independently selected from halogen atoms, C 1 -C 4 alkyl groups, C 1 -C 4 haloalkyl groups, C 1 -C 4 alkoxy groups, or C 1 -C 4 haloalkoxy groups 3-benzoylphenyl.
    [3" claim-type="Currently amended] The compound of claim 2, wherein Ar 1 is independently selected from a halogen atom, a C 1 -C 4 alkyl group, a C 1 -C 4 haloalkyl group, a C 1 -C 4 alkoxy group, or a C 1 -C 4 haloalkoxy group 3-phenoxyphenyl optionally substituted with up to 5 groups.
    [4" claim-type="Currently amended] 4. The compound of claim 3, wherein R is hydrogen and R 1 is isopropyl, trifluoromethyl or cyclopropyl, or R and R 1 are taken together with the carbon atom to which they are attached to form a cyclopropyl group;
    Ar is 4-chlorophenyl, 4-fluorophenyl, 4- (trifluoromethoxy) phenyl or 4-ethoxyphenyl;
    Ar 1 is 4-fluoro-3-phenoxyphenyl, m- (p-fluorophenoxy) phenyl, 4-fluoro-3- (p-fluorophenoxy) phenyl or 3-phenoxyphenyl .
    [5" claim-type="Currently amended] The compound of claim 4, wherein the compound is 1- (p-chlorophenyl) -1- [2-fluoro-3- (4-fluoro-3-phenoxyphenyl) propenyl] cyclopropane, (Z)-;
    2,5,5,5-tetrafluoro-4- (p-fluorophenyl) -1- (m-phenoxyphenyl) -2-pentene, (Z)-;
    4- (p-chlorophenyl) -2-fluoro-1- (4-fluoro-3-phenoxyphenyl) -5-methyl-2-hexene, (Z)-;
    1- [1- (p-chlorophenyl) -3-fluoro-4- (4-fluoro-3-phenoxyphenyl) -2-butenyl] cyclopropane, (Z)-;
    1- {1- (p-chlorophenyl) -3-fluoro-4- [4-fluoro-3- (p-fluorophenoxy) phenyl] -2-butenyl} cyclopropane, (Z)- ; And
    1- [3-fluoro-4- (4-fluoro-3-phenoxyphenyl) -1- [p- (trifluoromethoxy) phenyl] -2-butenyl} cyclopropane, (Z)- Method selected from the group consisting of:
    [6" claim-type="Currently amended] The method of claim 1, further comprising topically applying the composition containing the compound to the skin, leather, hair, feathers, or hair of an animal or human.
    [7" claim-type="Currently amended] The method of claim 6, wherein the animal is selected from the group consisting of cattle, sheep, horses, deer, camels, pigs, goats, ferrets, mink, rabbits, amphibians, reptiles, fish, birds, poultry, dogs and cats.
    [8" claim-type="Currently amended] The method of claim 6 for controlling and preventing invasion and infection by flies, fleas, teeth, mosquitoes, horns, mites and ticks.
    [9" claim-type="Currently amended] The method of claim 1, wherein the compound is administered orally, intragastrically or in rumen to an animal or human.
    [10" claim-type="Currently amended] The method of claim 1, wherein the compound is parenterally administered to an animal or human.
    [11" claim-type="Currently amended] The method of claim 1 wherein the animal is selected from the group consisting of cattle, sheep, horses, deer, camels, pigs, goats, ferrets, mink, rabbits, amphibians, reptiles, fish, birds, poultry, dogs and cats.
    [12" claim-type="Currently amended] The method of claim 1, wherein the compound is administered or applied in combination or in parallel with one or more synergists.
    [13" claim-type="Currently amended] The method of claim 1, wherein the compound is administered or applied in combination or in parallel with one or more other antiparasitic compounds.
    [14" claim-type="Currently amended] The method of claim 1, wherein the composition containing the compound is applied to an animal or human environment.
    [15" claim-type="Currently amended] A composition for controlling, preventing and protecting against invasion and infection by arthropods of animals and humans, comprising an agriculturally or pharmaceutically acceptable carrier and an antiparasitic amount of a compound of formula (1).
    Formula 1

    In the above formula,
    R, R 1 , Ar and Ar 1 are as defined in claim 1 .
    [16" claim-type="Currently amended] The composition of claim 15, wherein R, R 1 , Ar and Ar 1 are as defined in claim 2.
    [17" claim-type="Currently amended] The compound of claim 16, wherein Ar 1 is independently selected from a halogen atom, a C 1 -C 4 alkyl group, a C 1 -C 4 haloalkyl group, a C 1 -C 4 alkoxy group, or a C 1 -C 4 haloalkoxy group 3-phenoxyphenyl optionally substituted with up to 5 groups.
    [18" claim-type="Currently amended] 18. The compound of claim 17, wherein R is hydrogen and R 1 is isopropyl, trifluoromethyl or cyclopropyl, or R and R 1 are taken together with the carbon atom to which they are attached to form a cyclopropyl group;
    Ar is 4-chlorophenyl, 4-fluorophenyl, 4- (trifluoromethoxy) phenyl or 4-ethoxyphenyl;
    Ar 1 is 4-fluoro-3-phenoxyphenyl, m- (p-fluorophenoxy) phenyl, 4-fluoro-3- (p-fluorophenoxy) phenyl or 3-phenoxyphenyl .
    [19" claim-type="Currently amended] The composition of claim 15 further comprising one or more synergists.
    [20" claim-type="Currently amended] The composition of claim 15 further comprising one or more other antiparasitic compounds.
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    同族专利:
    公开号 | 公开日
    JPH11279005A|1999-10-12|
    IL127856D0|1999-10-28|
    CN1229647A|1999-09-29|
    HU9900207D0|1999-03-29|
    AR018269A1|2001-11-14|
    AU1428599A|2000-06-08|
    SK11499A3|2000-06-12|
    EP0933026A1|1999-08-04|
    CA2260431A1|1999-07-30|
    NZ333974A|2000-09-29|
    CZ26199A3|1999-08-11|
    BR9900270A|2000-03-28|
    HU9900207A2|2000-01-28|
    HU9900207A3|2000-03-28|
    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    法律状态:
    1998-01-30|Priority to US1636298A
    1998-01-30|Priority to US9/016,362
    1999-01-25|Application filed by 윌리암 에이취 캘넌, 에곤 이 버그, 아메리칸사이아나미드컴파니
    1999-08-25|Publication of KR19990068104A
    优先权:
    申请号 | 申请日 | 专利标题
    US1636298A| true| 1998-01-30|1998-01-30|
    US9/016,362|1998-01-30|
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