US20150105398A1 - Isoxazoline-substituted benzamide compound and pesticide - Google Patents

Isoxazoline-substituted benzamide compound and pesticide Download PDF

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Publication number
US20150105398A1
US20150105398A1 US14/568,964 US201414568964A US2015105398A1 US 20150105398 A1 US20150105398 A1 US 20150105398A1 US 201414568964 A US201414568964 A US 201414568964A US 2015105398 A1 US2015105398 A1 US 2015105398A1
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Prior art keywords
alkyl
substituted
atom
phenyl
haloalkyl
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US14/568,964
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Takeshi Mita
Takamasa Kikuchi
Takashi Mizukoshi
Manabu Yaosaka
Mitsuaki Komoda
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Nissan Chemical Corp
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Nissan Chemical Corp
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Application filed by Nissan Chemical Corp filed Critical Nissan Chemical Corp
Priority to US14/568,964 priority Critical patent/US20150105398A1/en
Publication of US20150105398A1 publication Critical patent/US20150105398A1/en
Priority to US15/097,002 priority patent/US10045969B2/en
Priority to US15/972,939 priority patent/US10596157B2/en
Assigned to NISSAN CHEMICAL CORPORATION reassignment NISSAN CHEMICAL CORPORATION CHANGE OF NAME (SEE DOCUMENT FOR DETAILS). Assignors: NISSAN CHEMICAL INDUSTRIES, LTD.
Priority to US16/508,818 priority patent/US10874645B2/en
Priority to US16/709,370 priority patent/US20200155511A1/en
Priority to US18/147,470 priority patent/US20230355590A1/en
Abandoned legal-status Critical Current

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    • 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
    • A61K31/421—1,3-Oxazoles, e.g. pemoline, trimethadione
    • 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
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    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
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    • C07C323/09—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and halogen atoms, or nitro or nitroso groups bound to the same carbon skeleton having sulfur atoms of thio groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
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    • C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D261/14—Nitrogen atoms
    • C07D261/16—Benzene-sulfonamido isoxazoles
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Definitions

  • the present invention relates to a novel isoxazoline-substituted benzamide compound and the salt thereof, and a pesticide characterized by containing the compound as an active ingredient.
  • the pesticide in the present invention means a pest controlling agent applied for harmful arthropods in agricultural and horticultural field or livestock farming and hygienic field (endo-parasiticides and ecto-parasiticides for mammals or birds as domestic animals or pets, or hygienic pest- or unpleasant pest-controlling agents for domestic or business use).
  • agricultural chemicals in the present invention mean insecticides, acaricides (miticides), nematicides, herbicides and fungicides, and the like.
  • isoxazoline-substituted benzoic acid amide compounds the followings are known: a report of synthesis by use of solid phase synthesis of 4-(5-methyl-5-substituted pyrrolyl-4,5-dihydroisoxazole-3-yl)benzoic acid amide derivatives (see, Non-patent Document 1); 4-(5-pyridyl-4,5-dihydroisoxazole-3-yl)benzoic acid amide derivatives have matrix metalloprotease and TNF-inhibition activity, or the like, and can be used as an anti-inflammatory agent or a chondro-protective agent (see, Patent Document 1); 4-(5-substituted carbamoylmethyl-4,5-dihydroisoxazole-3-yl)benzoic acid amide derivatives, 3-(5-substituted carbamoylmethyl-5-substituted alkyl-4,5-dihydroisoxazole-3
  • 3-(4-substituted phenyl)-4,5-dihydroisoxazole derivatives 5-substituted alkyl-3,5-bis substituted phenyl-4,5-dihydroisoxazole derivatives (see, Patent Document 7), 3-alkoxyphenyl-5-substituted-5-phenyl-4,5-dihydroisoxazole derivatives (see, Patent Document 8), 3-alkoxyphenyl-5-substituted alkyl-5-substituted carbamoyl-4,5-dihydroisoxazole derivatives (see, Patent Document 9), 3-(4-halophenyl)-5-substituted-5-substituted phenyl-4,5-dihydroisoxazole derivatives (see, Patent Documents 10 and Non-patent Document 2), and 3-(4-nitrophenyl)-5-substituted-5-substituted phenyl-4,5-
  • 4-hydroxyiminomethyl benzoic acid amide derivatives 4-hydroxyiminomethyl-N,N-dimethyl benzoic acid amide (see, Non-patent Document 4), 4-hydroxyiminomethyl benzoyl piperidine derivatives (see, Patent Documents 12 and 13), 4-hydroxyiminomethyl-N-bicycloalkyl benzoic acid amide derivatives (see, Patent Document 14), and 6-(hydroxyiminomethyl)pyridine-2-carboxamide derivatives (see, Non-patent Document 5), etc. are known.
  • 4-hydroxyiminomethyl benzoic acid amide derivatives that can be used as a production intermediate of the pesticides according to the present invention are not described in any documents and thus novel compounds.
  • haloalkenylbenzene derivatives substituted 3,3,3-trifluoro-2-propenylbenzene derivatives (see, Non-patent Documents 6-8), etc. are known.
  • specific substituted haloalkenylbenzene derivatives that can be used as a production intermediate of the pesticides according to the present invention are not described in any documents and thus novel compounds.
  • novel isoxazoline-substituted benzamide compounds of formula (I) are extremely useful compounds having excellent pest controlling activity, particularly insecticidal activity and acaricidal activity, and having little adverse affect on non-targeted beings such as mammals, fishes and useful insects, etc.
  • the present invention has been accomplished.
  • the present invention relates to the following aspects (1) to (15):
  • a 1 , A 2 and A 3 independently of one another are carbon atom or nitrogen atom
  • G is benzene ring, nitrogen-containing 6-membered aromatic heterocyclic ring, furan ring, thiophene ring, or 5-membered aromatic heterocyclic ring containing two or more hetero atoms selected from oxygen atom, sulfur atom and nitrogen atom
  • W is oxygen atom or sulfur atom
  • X is halogen atom, cyano, nitro, azido, —SCN, —SF 5 , C 1 -C 6 alkyl, C 1 -C 6 alkyl arbitrarily substituted with R 4 , C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkyl arbitrarily substituted with R 4 , C 2 -C 6 alkenyl, C 2 -C 6 alkenyl arbitrarily substituted with R 4 , C 3 -C 8 cycloalkenyl, C 3 -C 8 halo
  • Z is halogen atom, cyano, nitro, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 4 alkoxy C 1 -C 4 alkyl, C 1 -C 4 haloalkoxy C 1 -C 4 alkyl, C 1 -C 4 alkylthio C 1 -C 4 alkyl, C 1 -C 4 haloalkylthio C 1 -C 4 alkyl, C 1 -C 4 alkylsulfinyl C 1 -C 4 alkyl, C 1 -C 4 haloalkylsulfinyl C 1 -C 4 alkyl, C 1 -C 4 alkylsulfonyl C 1 -C 4 alkyl, C 1 -C 4 haloalkylsulfonyl C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 haloalky
  • R 4 is halogen atom, cyano, C 3 -C 8 cycloalkyl, C 3 -C 8 halocycloalkyl, —OH, —OR 5 , —SH, —S(O) r R 5 , —N(R 10 )R 9 , —N(R 10 )CHO, —N(R 10 )C(O)R 9 , —N(R 10 )C(O)OR 9 , —N(R 10 )C(O)SR 9 , —N(R 10 )C(S)OR 9 , —N(R 10 )C(S)SR 9 , —N(R 10 )S(O) 2 R 9 , —C(O)OR 9 , —C(O)N(R 10 )R 9 , —Si(R 13 )(R 14 )R 12 , phenyl, phenyl substituted with (Z) p1 , D-1 to D
  • R 17 is C 1 -C 12 alkyl, C 1 -C 12 haloalkyl, C 1 -C 12 alkoxy C 1 -C 12 alkyl, cyano C 1 -C 12 alkyl, C 1 -C 12 alkoxycarbonyl C 1 -C 12 alkyl, phenyl C 1 -C 4 alkyl, phenyl C 1 -C 4 alkyl substituted with (Z) p1 , C 3 -C 12 alkenyl, C 3 -C 12 haloalkenyl, C 3 -C 12 alkynyl, C 3 -C 12 haloalkynyl, C 1 -C 12 alkylcarbonyl, C 1 -C 12 alkoxycarbonyl, —C(O)ON ⁇ C(CH 3 )SCH 3 , —C(O)ON ⁇ C(SCH 3 )C(O)N(CH 3 ) 2 , phenyl or phenyl substituted with (
  • X is halogen atom, cyano, nitro, —SF 5 , C 1 -C 6 alkyl, C 1 -C 6 alkyl arbitrarily substituted with R 4 , C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkyl arbitrarily substituted with R 4 , C 2 -C 6 alkenyl, C 2 -C 6 alkenyl arbitrarily substituted with R 4 , C 2 -C 6 alkynyl, C 2 -C 6 alkynyl arbitrarily substituted with R 4 , —OH, —OR 5 , —OSO 2 R 5 , —S(O) r R 5 , —C(O)OR 9 , —C(O)SR 9 , —C(O)NHR 10 , —C(O)N(R 10 )R 9 , —C(S)OR 9 , —C(S)SR 9 , —C(S)
  • G is G-1, G-3, G-4, G-13, G-14, G-17, G-18, G-20, G-21 or G-22,
  • X is halogen atom, cyano, nitro, —SF 5 , C 1 -C 6 alkyl, C 1 -C 6 alkyl arbitrarily substituted with R 4 , C 3 -C 8 cycloalkyl, C 3 -C 8 halocycloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, —OR 5 , —OSO 2 R 5 , —S(O) r R 5 , —C(O)OR 9 , —C(O)SR 9 , —C(S)OR 9 , —C(S)SR 9 , —C(S)NHR 10 , —C(S)N(R 10 )R 9 , —CH ⁇ NOR 11 , —C(R 9 ) ⁇ NOR 11 , —Si(R 13
  • G is G-1
  • X is halogen atom, cyano, nitro, —SF 5 , C 1 -C 6 alkyl, C 1 -C 6 alkyl arbitrarily substituted with R 4 , C 3 -C 8 cycloalkyl, C 3 -C 3 halocycloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, —OR 5 , —OSO 2 R 5 , —S(O) r R 5 or tri(C 1 -C 8 alkyl)silyl, when m is 2 or 3, each X may be identical with or different from each other, further, when two Xs are adjacent, the adjacent two Xs may form 5-membered or 6-membered ring together with carbon atoms to which the two Xs are bonded by forming —CF 2 OCF 2 —, —OC
  • R 9 is C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl C 1 -C 4 alkyl, C 1 -C 6 alkoxy C 1 -C 4 alkyl, C 1 -C 6 alkylthio C 1 -C 4 alkyl, cyano C 1 -C 6 alkyl, C 3 -C 8 cycloalkyl, C 3 -C 6 alkenyl or C 3 -C 6 alkynyl,
  • R 16 is halogen atom, cyano, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, —OR 25 , —N(R 26 )R 25 , —S(O) r R 27 , —SO 2 NHR 29 , —SO 2 N(R 29 )R 28 , —C(O)R 28 , —C(O)OR 28 , —C(O)NHR 29 , —C(O)N(R 29 )R 28 , —C(O)N(R 29 )OR 28 , —C(S)NHR 29 , —C(S)N(R 29 )R 28 , —C(R 31 ) ⁇ NOH, —C(R 31 ) ⁇ NOR 30 , —C( ⁇ NR 31 )OR 30 , —C( ⁇ NR 31 )SR 30 , phenyl, phenyl substituted with (Z) p1
  • a 1 is carbon atom or nitrogen atom
  • X 1 is halogen atom, —SF 5 , C 1 -C 6 haloalkyl, hydroxy C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy C 1 -C 6 haloalkyl, C 1 -C 6 haloalkoxy C 1 -C 6 haloalkyl, C 3 -C 8 halocycloalkyl, C 1 -C 6 haloalkoxy, C 1 -C 3 haloalkoxy C 1 -C 3 haloalkoxy, C 1 -C 6 haloalkylthio, C 1 -C 6 haloalkylsulfinyl or C 1 -C 6 haloalkylsulfonyl, X 2 is halogen atom, cyano, nitro, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, —OR 5
  • a 1 is carbon atom or nitrogen atom
  • J is hydrogen atom or halogen atom
  • W is oxygen atom or sulfur atom
  • Y is halogen atom, cyano, nitro, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 6 alkylsulfonyl, C 1 -C 6 haloalkylsulfonyl or —N(R 7 )R 6
  • R 1 is C 1 -C 6 alkyl, C 1 -C 6 alkyl arbitrarily substituted with R 16 , C 3 -C 6 cycloalkyl, E-4, E-5, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, —N(R 20 )R 19 , phenyl substituted with (Z
  • Z is halogen atom, cyano, nitro, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylsulfonyl, C 1 -C 6 haloalkylsulfonyl, C 1 -C 6 alkoxycarbonyl, —C(O)NH 2 , C 1 -C 6 alkylaminocarbonyl, di(C 1 -C 6 alkyl)aminocarbonyl, —C(S)NH 2 , —S(O) 2 NH 2 , C 1 -C 6 alkylaminosulfonyl or di(C 1 -C 6 alkyl)aminosulfonyl, when p1, p2, p3 or p4 is an integer of 2 or more, each Z may be identical with or different from each other, R 15 is C 1 -C
  • R 19 is C 1 -C 6 haloalkyl, —C(O)R 28 , —C(O)OR 28 , phenyl, phenyl substituted with (Z) p1 , D-3, D-4, D-21, D-47, D-50, D-51, D-53 or D-54
  • R 20 is hydrogen atom or C 1 -C 6 alkyl
  • R 22 is C 1 -C 4 alkyl
  • R 28 is C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 alkenyl or C 3 -C 6 alkynyl
  • R 29 is hydrogen atom or C 1 -C 6 alkyl
  • R 30 is C 1 -C 6 alkyl
  • R 31 is C 1 -C 6 alkyl
  • n is an integer of
  • X 1 is halogen atom, —SF 5 , C 1 -C 6 haloalkyl, hydroxy C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy C 1 -C 6 haloalkyl, C 3 -C 8 halocycloalkyl, C 1 -C 6 haloalkoxy, C 1 -C 3 haloalkoxy C 1 -C 3 haloalkoxy, C 1 -C 6 haloalkylthio, C 1 -C 6 haloalkylsulfinyl or C 1 -C 6 haloalkylsulfonyl, X 3 is hydrogen atom, halogen atom, cyano, nitro, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy or C 1 -C 6 alkylthio, X 4 is hydrogen atom, halogen atom, hal
  • R 3 is —C(R 3a )(R 3b )R 3c ,
  • R 3a and R 3b independently of each other are halogen atom, or R 3a and R 3b together may form 3- to 6-membered ring together with the carbon atom bonding them by forming C 2 -C 6 haloalkylene chain
  • R 3c is hydrogen atom, halogen atom, C 1 -C 6 alkyl, C 1 -C 5 haloalkyl, C 1 -C 4 haloalkoxy or C 1 -C 4 haloalkylthio, with a proviso that in case where X 1 is fluorine atom, chlorine atom or trifluoromethyl and both X 2 and X 3 are hydrogen atom, in case where both X 1 and X 2 are fluorine atom and X 3 is hydrogen atom, and in case where both X 1 and X 2 are trifluoromethyl and X 3 is hydrogen atom, R 3c is hydrogen atom, chlorine atom, bromine atom, iodine atom, C 1 -
  • a pesticide containing as an active ingredient one or more selected from isoxazoline-substituted benzamide compound and the salt thereof as set forth in (1) to (5) (13) An agrochemical containing as an active ingredient one or more selected from isoxazoline-substituted benzamide compound and the salt thereof as set forth in (1) to (5).
  • the compound according to the present invention has an excellent insecticidal and acaricidal activity for many agricultural insect pests, spider mites, endo- or ecto-parasiticide for mammals or birds, and exerts a control effect sufficient for pest insects that acquire resistance against exiting insecticides. Further, the compound has little adverse affect on mammals, fishes and beneficial insects, and has a low persistency and a low impact on the environment. Therefore, the present invention can provide a useful and novel pesticide.
  • Active compounds used as the pesticide in the present invention are generally the compounds of formulae (1) to (5) mentioned above, and the compounds of formulae (6) to (11) mentioned above are novel production intermediates used for the production of these active compounds. These intermediates contain specific compounds themselves having control activity against specific pests that can be used as a control agent for the pest.
  • some compounds have geometrical isomers of E-form and Z-form depending on the kind of substituents.
  • the present invention includes these E-forms, Z-forms and mixtures containing E-form and Z-form in an arbitrary proportion.
  • the compounds included in the present invention have optically active forms resulting from the presence of 1 or more asymmetric carbon atoms, and the present invention includes all optically active forms or racemates.
  • some compounds wherein R 2 is hydrogen atom are present in tautomer, and the present invention includes these structures,
  • the compounds included in the present invention can be converted to acid addition salts for example salts of hydrohalide acid such as hydrofluoric acid, hydrochloric acid, hydrobromic acid, hydriodic acid or the like, salts of inorganic acids such as nitric acid, sulfuric acid, phosphoric acid, chloric acid, perchloric acid or the like, salts of sulfonic acid such as methansulfonic acid, ethansulfonic acid, trufluoromethansulfonic acid, benzene sulfonic acid, p-toluene sulfonic acid or the like, salts of carboxylic acid such as formic acid, acetic acid, propionic acid, trifluoroacetic acid, fumaric acid, tartaric acid, oxalic acid, maleic acid, malic acid, succinic acid, benzoic acid, mandelic acid, ascorbic acid, lactic acid, gluconic acid, citric acid or the like, or salt
  • the compounds included in the present invention can be converted to matal salts for example salts of alkali metal such as lithium, sodium, potassium, salts of alkaline earth metal such as calcium, barium, magnesium, or salts of aluminum, according to a conventional method.
  • alkali metal such as lithium, sodium, potassium
  • alkaline earth metal such as calcium, barium, magnesium, or salts of aluminum
  • n- means normal
  • i- means iso
  • s- means secondary
  • t- means tertiary
  • Ph means phenyl
  • Halogen atom in the compounds of the present invention includes fluororine atom, chlorine atom, bromine atom and iodine atom. In the interim, the indication of “halo” in the specification also means these halogen atoms.
  • C a -C b haloalkyl means straight-chain or branched-chain hydrocarbon groups having carbon atom number of a to b that a hydrogen atom (hydrogen atoms) bonded to carbon atom is (are) arbitrarily substituted with a halogen atom (halogen atoms). In this case, if it is substituted with two or more halogen atoms, these halogen atoms may be identical with or different from each other.
  • cyano C a -C b alkyl means straight-chain or branched-chain alkyl groups having carbon atom number of a to b that a hydrogen atom (hydrogen atoms) bonded to carbon atom is (are) arbitrarily substituted with a cyano group (cyano groups).
  • cyano groups for example cyanomethyl, 1-cyanoethyl, 2-cyanoethyl, 2-cyanopropyl, 3-cyanopropyl, 2-cyanobutyl, and the like. It is selected from the scope of the indicated carbon atom number.
  • C a -C b cycloalkyl means cyclic hydrocarbon groups having carbon atom number of a to b, and can form 3-membered to 6-membered single ring or conjugated ring structure.
  • each ring may be arbitrarily substituted alkyl group in the scope of the indicated carbon atom number.
  • cyclopropyl 1-methylcyclopropyl, 2-methylcyclopropyl, 2,2-dimethylcyclopropyl, 2,2,3,3-tetramethylcyclopropyl, cyclobutyl, cyclopentyl, 2-methylcyclopentyl, 3-methylcyclopentyl, cyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, bicyclo[2.2.1]heptan-2-yl and the like. It is selected from the scope of the indicated carbon atom number.
  • these halogen atoms may be identical with or different from each other.
  • Concrete examples thereof are for example 2,2-dichlorocyclopropyl, 2,2-dibromocyclopropyl, 2,2-difluoro-1-methylcyclopropyl, 2,2-dichloro-1-methylcyclopropyl, 2,2-dibromo-1-methylcyclopropyl, 2,2-dichloro-3,3-dimethylcyclopropyl, 2,2,3,3-tetrafluorocyclobutyl, 2-trifluoromethylcyclohexyl, 3-trifluoromethylcyclohexyl, 4-trifluoromethylcyclohexyl and the like. It is selected from the scope of the indicated carbon atom number.
  • C a -C b halolkenyl means straight-chain or branched-chain unsaturated hydrocarbon groups having carbon atom number of a to b and having 1 or more double bonds, which a hydrogen atom (hydrogen atoms) bonded to carbon atom is (are) arbitrarily substituted with a halogen atom (halogen atoms). In this case, if it is substituted with two or more halogen atoms, these halogen atoms may be identical with or different from each other.
  • C a -C b cycloalkenyl means cyclic unsaturated hydrocarbon groups having carbon atom number of a to b and having 1 or more double bonds, and can form 3-membered to 6-membered single ring or conjugated ring structure.
  • each ring may be arbitrarily substituted alkyl group in the scope of the indicated carbon atom number, and further the double bond may be either endo- or exo-form.
  • Concrete examples thereof are for example 2-cyclopenten-1-yl, 3-cyclopenten-1-yl, 2-cyclohexen-1-yl, 3-cyclohexen-1-yl, bicyclo[2.2.1]-5-hepten-2-yl and the like. It is selected from the scope of the indicated carbon atom number.
  • halogen atom may be in the ring structure moiety, the side chain moiety or both of them. Further, if it is substituted with two or more halogen atoms, these halogen atoms may be identical with or different from each other. Concrete examples thereof are for example 2-chlorobicyclo[2.2.1]-5-hepten-2-yl and the like. It is selected from the scope of the indicated carbon atom number.
  • C a -C b alkynyl means straight-chain or branched-chain unsaturated hydrocarbon groups having carbon atom number of a to b and having 1 or more triple bonds. Concrete examples thereof are for example ethynyl, 1-propynyl, 2-propynyl, 1-methyl-2-propynyl, 2-butynyl, 2-pentynyl, 1-methyl-2-butynyl, 2-hexynyl, and the like. It is selected from the scope of the indicated carbon atom number.
  • C a -C b halolkynyl means straight-chain or branched-chain unsaturated hydrocarbon groups having carbon atom number of a to b and having 1 or more triple bonds, which a hydrogen atom (hydrogen atoms) bonded to carbon atom is (are) arbitrarily substituted with a halogen atom (halogen atoms). In this case, if it is substituted with two or more halogen atoms, these halogen atoms may be identical with or different from each other.
  • C a -C b alkoxy means alkyl-O— groups wherein the alkyl has carbon atom number of a to b, and includes for example methoxy, ethoxy, n-propyloxy, i-propyloxy, n-butyloxy, s-butyloxy, i-butyloxy, t-butyloxy, n-pentyloxy, n-hexyloxy and the like. It is selected from the scope of the indicated carbon atom number.
  • C a -C b haloalkoxy means haloalkyl-O— groups wherein the haloalkyl has carbon atom number of a to b, and includes for example difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2-chloro-1,1,2-trifluoroethoxy, 2-bromo-1,1,2-trifluoroethoxy, 2,2-dichloro-1,1,2-trifluoroethoxy, pentafluoroethoxy, 2,2,2-trichloro-1,1-difluoroethoxy, 2-bromo-1,1,2,2-tetrafluoroethoxy, 2,2,3,3-tetrafluoropropyloxy, 1,1,2,3,3,3-
  • C a -C b alkylthio means alkyl-S— groups wherein the alkyl has carbon atom number of a to b, and includes for example methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, s-butylthio, i-butylthio, t-butylthio, n-pentylthio, n-hexylthio and the like. It is selected from the scope of the indicated carbon atom number.
  • C a -C b haloalkylthio means haloalkyl-S— groups wherein the haloalkyl has carbon atom number of a to b, and includes for example difluoromethylthio, trifluoromethylthio, bromodifluoromethylthio, 2,2,2-trifluoroethylthio, 1,1,2,2-tetrafluoroethylthio, 1,1,2-trifluoro-2-chloroethylthio, pentafluoroethylthio, 2-bromo-1,1,2,2-tetrafluoroethylthio, heptafluoropropylthio, 1,2,2,2-tetrafluoro-1-trifluoromethylthio, 1,2,2,2-tetrafluoro-1-trifluoroethylthio, nonafluorobutylthio, and the like. It is selected from the scope of the indicated carbon atom
  • C a -C b alkylsulfinyl means alkyl-S(O)— groups wherein the alkyl has carbon atom number of a to b, and includes for example methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, i-propylsulfinyl, n-butylsulfinyl, s-butylsulfinyl, i-butylsulfinyl, t-butylsulfinyl, and the like. It is selected from the scope of the indicated carbon atom number.
  • C a -C b haloalkylsulfinyl means haloalkyl-S(O)— groups wherein the haloalkyl has carbon atom number of a to b, and includes for example difluoromethylsulfinyl, trifluoromethylsulfinyl, bromodifluoromethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, 2-bromo-1,1,2,2-tetrafluoroethylsulfinyl, 1,2,2,2-tetrafluoro-1-trifluoromethylethylsulfinyl, nonafluorobutylsulfinyl, and the like. It is selected from the scope of the indicated carbon atom number.
  • C a -C b alkylsulfonyl means alkyl-SO 2 — groups wherein the alkyl has carbon atom number of a to b, and includes for example methanesulfonyl, ethanesulfonyl, n-propylsulfonyl, i-propylsulfonyl, n-butylsulfonyl, s-butylsulfonyl, i-butylsulfonyl, t-butylsulfonyl, n-pentylsulfonyl, n-hexylsulfonyl, and the like. It is selected from the scope of the indicated carbon atom number.
  • C a -C b haloalkylsulfonyl means haloalkyl-SO 2 — groups wherein the haloalkyl has carbon atom number of a to b, and includes for example difluoromethanesulfonyl, trifluoromethanesulfonyl, chlorodifluoromethanesulfonyl, bromodifluoromethanesulfonyl, 2,2,2-trifluoroethanesulfonyl, 1,1,2,2-tetrafluoroethanesulfonyl, 1,1,2-trifluoro-2-chloroethanesulfonyl, and the like. It is selected from the scope of the indicated carbon atom number.
  • C a -C b alkylamino means amino groups, which either hydrogen atom is substituted with the above-mentioned alkyl group having carbon atom number of a to b, and includes for example methylamino, ethylamino, n-propylamino, i-propylamino, n-butylamino, i-butylamino, t-butylamino, and the like. It is selected from the scope of the indicated carbon atom number.
  • C a -C b alkylcarbonyl means alkyl-C(O)— groups wherein the alkyl has carbon atom number of a to b, and includes for example CH 3 C(O)—, CH 3 CH 2 C(O)—, CH 3 CH 2 CH 2 C(O)—, (CH 3 ) 2 CHC(O)—, CH 3 (CH 2 ) 3 C(O)—, (CH 3 ) 2 CHCH 2 C(O)—, CH 3 CH 2 CH(CH 3 )C(O)—, (CH 3 ) 3 CC(O)—, CH 3 (CH 2 ) 4 C(O)—, CH 3 (CH 2 ) 5 C(O)—, and the like. It is selected from the scope of the indicated carbon atom number.
  • C a -C b haloalkylcarbonyl means haloalkyl-C(O)— groups wherein the haloalkyl has carbon atom number of a to b, and includes for example FCH 2 C(O)—, ClCH 2 C(O)—, F 2 CHC(O)—, Cl 2 CHC(O)—, CF 3 C(O)—, CICF 2 C(O)—, BrCF 2 C(O)—, CCl 3 C(O)—, CF 3 CF 2 C(O)—, ClCH 2 CH 2 CH 2 C(O)—, CF 3 CF 2 CF 2 C(O)—, ClCH 2 C(CH 3 ) 2 C(O)—, and the like. It is selected from the scope of the indicated carbon atom number.
  • C a -C b alkoxycarbonyl means alkyl-O—C(O)— groups wherein the alkyl has carbon atom number of a to b, and includes for example CH 3 OC(O)—, CH 3 CH 2 OC(O)—, CH 3 CH 2 CH 2 OC(O)—, (CH 3 ) 2 CHOC(O)—, CH 3 (CH 2 ) 3 OC(O)—, (CH 3 ) 2 CHCH 2 OC(O)—, (CH 3 ) 3 COC(O)—, and the like. It is selected from the scope of the indicated carbon atom number.
  • C a -C b haloalkoxycarbonyl means haloalkyl-O—C(O)— groups wherein the haloalkyl has carbon atom number of a to b, and includes for example ClCH 2 CH 2 OC(O)—, CF 3 CH 2 OC(O)—, and the like. It is selected from the scope of the indicated carbon atom number.
  • C a -C b alkylaminocarbonyl means carbamoyl groups, which either hydrogen atom is substituted with the above-mentioned alkyl group having carbon atom number of a to b, and includes for example CH 3 NHC(O)—, CH 3 CH 2 NHC(O)—, CH 3 CH 2 CH 2 NHC(O)—, (CH 3 ) 2 CHNHC(O)—, CH 3 (CH 2 ) 3 NHC(O)—, (CH 3 ) 2 CHCH 2 NHC(O)—, CH 3 CH 2 CH(CH 3 )NHC(O)—, (CH 3 ) 3 CNHC(O)—, and the like. It is selected from the scope of the indicated carbon atom number.
  • C a -C b haloalkylaminocarbonyl means carbamoyl groups, which either hydrogen atom is substituted with the above-mentioned haloalkyl group having carbon atom number of a to b, and includes for example 2-fluoroethylcarbamoyl, 2-chloroethylcarbamoyl, 2,2-difluorocarbamoyl, 2,2,2-trifluoroethylcarbamoyl, and the like. It is selected from the scope of the indicated carbon atom number.
  • di(C a -C b alkyl)aminocarbonyl means carbamoyl groups, which both hydrogen atoms are substituted with the above-mentioned alkyl group having carbon atom number of a to b that may be identical with or different from each other, and includes for example (CH 3 ) 2 NC(O)—, CH 3 CH 2 N(CH 3 )C(O)—, (CH 3 CH 2 ) 2 NC(O)—, (CH 3 CH 2 CH 2 ) 2 NC(O)—, (CH 3 CH 2 CH 2 CH 2 ) 2 NC(O)—, and the like. It is selected from the scope of the indicated carbon atom number.
  • C a -C b alkylaminosulfonyl means sulfamoyl groups, which either hydrogen atom is substituted with the above-mentioned alkyl group having carbon atom number of a to b, and includes for example CH 3 NHSO 2 —, CH 3 CH 2 NHSO 2 —, CH 3 CH 2 CH 2 NHSO 2 —, (CH 3 ) 2 CHNHSO 2 —, CH 3 (CH 2 ) 3 NHSO 2 —, (CH 3 ) 2 CHCH 2 NHSO 2 —, CH 3 CH 2 CH(CH 3 )NHSO 2 —, (CH 3 ) 3 CNHSO 2 , and the like. It is selected from the scope of the indicated carbon atom number.
  • the indication of “di(C a -C b alkyl)aminosulfonyl” means sulfamoyl groups, which both hydrogen atoms are substituted with the above-mentioned alkyl group having carbon atom number of a to b that may be identical with or different from each other, and includes for example (CH 3 ) 2 NSO 2 —, CH 3 CH 2 N(CH 3 )SO 2 —, (CH 3 CH 2 ) 2 NSO 2 —, (CH 3 CH 2 CH 2 ) 2 NSO 2 —, (CH 3 CH 2 CH 2 CH 2 ) 2 NSO 2 —, and the like. It is selected from the scope of the indicated carbon atom number.
  • tri(C a -C b alkyl)silyl means silyl groups substituted with the above-mentioned alkyl group having carbon atom number of a to b that may be identical with or different from each other, and includes for example trimethylsilyl, triethylsilyl, tri(n-propyl)silyl, ethyldimethylsilyl, n-propyldimethylsilyl, n-butyldimethylsilyl, i-butyldimethylsilyl, t-butyldimethylsilyl, and the like. It is selected from the scope of the indicated carbon atom number.
  • C a -C b alkylcarbonyloxy means alkylcarbonyl-O— groups wherein the alkyl has carbon atom number of a to b, and includes for example CH 3 C(O)—O—, CH 3 CH 2 C(O)—O—, CH 3 CH 2 CH 2 C(O)—O—, (CH 3 ) 2 CHC(O)—O—, CH 3 (CH 2 ) 3 C(O)—O—, (CH 3 ) 2 CHCH 2 C(O)—O—, CH 3 CH 2 CH(CH 3 )C(O)—O—, (CH 3 ) 3 CC(O)—O—, and the like. It is selected from the scope of the indicated carbon atom number.
  • C a -C b alkylsulfonyloxy means alkylsulfonyl-O— groups wherein the alkyl has carbon atom number of a to b, and includes for example CH 3 SO 2 —O—, CH 3 CH 2 SO 2 —O—, CH 3 CH 2 CH 2 SO 2 —O—, (CH 3 ) 2 CHSO 2 —O—, and the like. It is selected from the scope of the indicated carbon atom number.
  • C a -C b haloalkylsulfonyloxy means haloalkylsulfonyl-O— groups wherein the haloalkyl has carbon atom number of a to b, and includes for example difluoromethanesulfonyl-O—, trifluoromethanesulfonyl-O—, chlorodifluoromethanesulfonyl-O—, bromodifluoromethanesulfonyl-O—, and the like. It is selected from the scope of the indicated carbon atom number.
  • the indication of “C a -C b alkyl arbitrarily substituted with R 4 ”, “C a -C b alkyl arbitrarily substituted with R 16 ”, “C a -C b alkyl arbitrarily substituted with R 24 ”, “C a -C b alkyl arbitrarily substituted with R 32 ”, or “C a -C b alkyl arbitrarily substituted with R 35 ” means straight-chain or branched-chain hydrocarbon groups having carbon atom number of d to e, which a hydrogen atom (hydrogen atoms) bonded to carbon atom is (are) arbitrarily substituted with R 4 , R 16 , R 24 , R 32 or R 35 . It is selected from the scope of the indicated carbon atom number.
  • R 4 , R 16 , R 24 , R 32 or R 35 may be identical with or different from each other.
  • the indication of “hydroxy C d -C e cycloalkyl”, “C a -C b alkoxy C d -C e cycloalkyl”, “C a -C b alkenyl C d -C e cycloalkyl” or “C a -C b haloalkenyl C d -C e cycloalkyl” means the cycloalkyl having carbon atom number of d to e, which a hydrogen atom (hydrogen atoms) bonded to carbon atom is (are) arbitrarily substituted with C a -C b alkoxy, C a -C b alkenyl, C a -C b haloalkenyl or hydroxy. It is selected from the scope of the indicated carbon atom number.
  • the indication of “C a -C b cycloalkyl arbitrarily substituted with R 4 ”, “C a -C b cycloalkyl arbitrarily substituted with R 16 ”, “C a -C b cycloalkyl arbitrarily substituted with R 24 ” or “C a -C b cycloalkyl arbitrarily substituted with R 32 ” means the cycloalkyl groups having carbon atom number of a to b, which a hydrogen atom (hydrogen atoms) bonded to carbon atom is (are) arbitrarily substituted with R 4 , R 16 , R 24 or R 32 .
  • R 4 , R 16 , R 24 or R 32 may be in the ring structure moiety, the side chain moiety or both of them. In this case, when two or more substituents R 4 , R 16 , R 24 or R 32 are present on the C a -C b cycloalkyl, respective R 4 , R 16 , R 24 or R 32 may be identical with or different from each other.
  • phenyl C a -C b alkenyl or “phenyl C a -C b alkenyl substituted with (Z) p1 ” means the alkenyl having carbon atom number of a to b, which a hydrogen atom (hydrogen atoms) bonded to carbon atom is (are) arbitrarily substituted phenyl or phenyl substituted with (Z) p1 . It is selected from the scope of the indicated carbon atom number.
  • the indication of “C a -C b alkenyl arbitrarily substituted with R 4 ”, “C a -C b alkenyl arbitrarily substituted with R 16 ”, “C a -C b alkenyl arbitrarily substituted with R 24 ” or “C a -C b alkenyl arbitrarily substituted with R 32 ” means the alkenyl groups having carbon atom number of a to b, which a hydrogen atom (hydrogen atoms) bonded to carbon atom is (are) arbitrarily substituted with R 4 , R 16 , R 24 or R 32 . It is selected from the scope of the indicated carbon atom number.
  • phenyl C a -C b alkynyl or “phenyl C a -C b alkynyl substituted with (Z) p1 ” means the alkynyl having carbon atom number of a to b, which a hydrogen atom (hydrogen atoms) bonded to carbon atom is (are) arbitrarily substituted phenyl or phenyl substituted with (Z) p1 . It is selected from the scope of the indicated carbon atom number.
  • the indication of “C a -C b alkynyl arbitrarily substituted with R 4 ”, “C a -C b alkynyl arbitrarily substituted with R 16 ”, “C a -C b alkynyl arbitrarily substituted with R 24 ” or “C a -C b alkynyl arbitrarily substituted with R 32 ” means the alkynyl groups having carbon atom number of a to b, which a hydrogen atom (hydrogen atoms) bonded to carbon atom is (are) arbitrarily substituted with R 4 , R 16 , R 24 or R 32 . It is selected from the scope of the indicated carbon atom number. In each other.
  • R 1 and R 2 together may form 3- to 8-membered ring together with the nitrogen atom bonding them by forming C 2 to C 7 alkylene chain, in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom”,
  • R 10 together with R 9 may form 3- to 7-membered ring with the nitrogen atom bonding them by forming C 2 -C 6 alkylene chain
  • the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom
  • “R 18 together with R 17 may form 5- to 8-membered ring with the nitrogen atom bonding them by forming C 4 -C 7 alkylene chain
  • the alkylene chain may contain one oxygen atom or sulfur atom
  • R 26 together with R 25 may form 3- to 6-membered ring with the nitrogen atom bonding them by forming C 2 -C 5 alkylene chain
  • the alkylene chain may contain one oxygen atom or sulfur atom
  • “R 29 together with R 28 may form 3- to 6-membered ring with the nitrogen atom bonding them by forming C 2 -C 5 alkylene chain
  • the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom”
  • “R 34 together with R 33 may form
  • the combination of the atoms of A 1 , A 2 and A 3 includes for example the following groups.
  • A-I A 1 , A 2 and A 3 are carbon atoms.
  • A-II A 1 is nitrogen atom, A 2 and A 3 are carbon atoms.
  • A-III A 2 is nitrogen atom, A 1 and A 3 are carbon atoms.
  • A-IV A 1 and A 3 are nitrogen atom, A 2 is carbon atom.
  • A-V A 2 and A 3 are nitrogen atom, A 1 is carbon atom.
  • the substituent G includes for example aromatic 6-membered rings shown in any one of G-1 to G-10 and aromatic 5-membered rings shown in any one of G-11 to G-25.
  • aromatic 6-membered rings shown in G-1, G-3 and G-4 and aromatic 5-membered rings shown in any one of G-13, G-14, G-17, G-18, G-20, G-21 and G-22 are preferable, and aromatic 6-membered ring shown in G-1 is particularly preferable.
  • the substituent W includes for example oxygen atom or sulfur atom.
  • the substituent X includes for example the following groups.
  • m is an integer of 2 or more, Xs may be identical with or different from each other.
  • X-I halogen atom and C 1 -C 6 haloalkyl.
  • X-II halogen atom, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 alkylsulfonyloxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl and C 1 -C 6 alkylsulfonyl.
  • X-III halogen atom, C 1 -C 6 haloalkyl, C 1 -C 6 haloalkoxy, C 1 -C 3 haloalkoxy C 1 -C 3 haloalkoxy, C 1 -C 6 haloalkylsulfonyloxy, C 1 -C 6 haloalklylthio, C 1 -C 6 haloalkylsulfinyl and C 1 -C 6 haloalkylsulfonyl.
  • X-IV halogen atom, C 1 -C 6 haloalkyl, cyano, nitro, —SF 5 and —Si(R 13 )(R 14 )R 12 wherein R 12 is C 1 -C 6 alkyl, phenyl or phenyl substituted with (Z) p1 , R 13 and R 14 independently of each other are C 1 -C 6 alkyl.
  • X-V halogen atom and C 1 -C 6 alkyl arbitrarily substituted with R 4 wherein R 4 is halogen atom, cyano, —OH, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 haloalkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 haloalkylsulfonyl or tri(C 1 -C 6 alkyl)silyl.
  • X-VI halogen atom, C 1 -C 6 haloalkyl, C 3 -C 8 cycloalkyl, C 3 -C 8 halocycloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, E-10, E-12, E-18, E-32, E-35 and E-43.
  • X-VII halogen atom, C 1 -C 6 haloalkyl, —OR 5 , —OSO 2 R 5 and —S(O) r R 5 wherein R 5 is C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 3 haloalkoxy C 1 -C 3 haloalkyl, C 3 -C 8 cycloalkyl, C 3 -C 8 halocycloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 3 -C 6 alkynyl, C 3 -C 6 haloalkynyl, E-4 to E-9, E-23 to E-27 or E-28, r is an integer of 0 to 2.
  • X-VIII halogen atom, C 1 -C 6 haloalkyl, —C(O)OR 9 , —C(O)SR 9 , —C(S)OR 9 , —C(S)SR 9 , —C(S)NHR 10 , —C(S)N(R 10 )R 9 , —CH ⁇ NOR 11 and —C(R 9 ) ⁇ NOR 11
  • R 9 is C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 8 cycloalkyl or C 3 -C 8 halocycloalkyl
  • R 10 is hydrogen atom or C 1 -C 6 alkyl, or R 10 together with R 9 may form 5- or 6-membered ring with the nitrogen atom bonding them by forming C 4 -C 5 alkylene chain, in this case, the alkylene chain may contain one oxygen atom or sulfur atom
  • R 11 is C 1 -C 6 alky
  • X-IX m is 2, two adjacent Xs form 5- or 6-membered ring with the carbon atom bonding them by forming —CF 2 OCF 2 —, —OCF 2 O—, —CF 2 OCF 2 O— or —OCF 2 CF 2 O—.
  • m indicating the number of substituent X is an integer of 0 to 5.
  • m is preferably 1, 2 and 3.
  • the substituent Y includes for example the following groups.
  • n is an integer of 2 or more, Ys may be identical with or different from each other.
  • Y-I halogen atom, C 1 -C 6 alkyl and C 1 -C 6 haloalkyl.
  • Y-II halogen atom, C 1 -C 6 alkyl, cyano, nitro, —C(O)NH 2 and —C(S)NH 2 .
  • Y-III halogen atom, C 1 -C 6 alkyl and C 1 -C 6 alkyl arbitrarily substituted with C 1 -C 6 alkyl and R 4 wherein R 4 is halogen atom, cyano, —OH, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 haloalkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 haloalkylsulfonyl or tri(C 1 -C 6 alkyl)silyl.
  • Y-IV halogen atom, C 1 -C 6 alkyl, —OR 5 , —OSO 2 R 5 and —S(O) r R 5 wherein R 5 is C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 3 haloalkoxy C 1 -C 3 haloalkyl, C 3 -C 8 cycloalkyl, C 3 -C 8 halocycloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 3 -C 6 alkynyl, C 3 -C 6 haloalkynyl, E-4 to E-9, E-23 to E-27 or E-28, r is an integer of 0 to 2.
  • Y-V halogen atom, C 1 -C 6 alkyl, —NHR 7 , —N(R 7 )R 6 wherein R 6 is C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, —S(O) 2 R 9 , —CHO, —C(O)R 9 , —C(O)OR 9 , —C(O)SR 9 , —C(S)OR 9 or —C(S)SR 9 , R 7 is hydrogen atom, C 1 -C 6 alkyl or C 1 -C 6 haloalkyl, R 9 is C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 8 cycloalkyl or C 3 -C 3 halocycloalkyl and —N ⁇ C(R 9 )OR 8 wherein R 8 is C 1 -C 6 alkyl, R 9 is C 1 -C 6 alkyl or C
  • Y-VI halogen atom, nitro, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkylthio, C 1 -C 6 alkylamino and di(C 1 -C 6 alkyl)amino.
  • n indicating the number of substituent Y is an integer of 0 to 4. Among them, n is preferably 0 and 1.
  • the substituent R 1 includes for example the following groups.
  • R 1 -I C 1 -C 6 alkyl, C 1 -C 6 alkyl arbitrarily substituted with R 16 (wherein R 16 is halogen atom, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, phenyl, phenyl substituted with (Z) p1 , D-1 to D-4, D-8 to D-38, D-47 to D-55, E-4 to E-12, E-18, E-19, E-32, E-35, E-43, M-2, M-3, M-5, M-8, M-9 or M-10), C 3 -C 8 cycloalkyl and C 3 -C 3 halocycloalkyl.
  • R 1 -II C 1 -C 6 alkyl arbitrarily substituted with —OR 25 wherein R 25 is C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylaminocarbonyl, di(C 1 -C 6 alkyl)aminocarbonyl or C 1 -C 6 alkylsulfonyl.
  • R 1 -III C 1 -C 6 alkyl arbitrarily substituted with —N(R 26 )R 25 wherein R 25 is C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylaminocarbonyl, di(C 1 -C 6 alkyl)aminocarbonyl or C 1 -C 6 alkylsulfonyl, R 26 is hydrogen or C 1 -C 6 alkyl.
  • R 1 -IV C 1 -C 6 alkyl arbitrarily substituted with —S(O) r R 27 wherein R 27 is C 1 -C 6 alkyl, C 1 -C 6 haloalkyl or tri(C 1 -C 4 alkyl)silyl C 1 -C 4 alkyl, r is an integer of 0 to 2.
  • R 1 -V C 1 -C 6 alkyl arbitrarily substituted with R 16 wherein R 16 is cyano, —C(O)R 28 , —C(O)OR 28 , —C(O)NHR 29 , —C(O)N(R 29 )R 28 , —C(O)N(R 29 )OR 28 , —C(S)NHR 29 , —C(S)N(R 29 )R 28 , —SO 2 NHR 29 , —SO 2 N(R 29 )R 28 , —C(R 31 ) ⁇ NOH, —C(R 31 ) ⁇ NOR 30 , —C( ⁇ NR 31 )OR 30 or —C( ⁇ NR 31 )SR 36 , R 28 is C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl C 1 -C 4 alkyl, C 1 -C 6 alkoxy C 1
  • R 1 -VI C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, C 3 -C 6 haloalkynyl, phenyl substituted with (Z) p1 , D-8, D-10, D-11, D-13 to D-15, D-17, D-18, D-21 to D-23, D-26 to D-37, D-39, D-40, D-42, D-45, D-47 to D-54, D-56, D-58, E-4, E-5, E-7 and E-9
  • R 1 -VII —N(R 20 )R 19 wherein R 19 is C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, —C(O)R 28 , —C(O)OR 28 , —C(O)NHR 29 , —C(O)N(R 29 )R 28 , —C(S)NHR
  • R 1 -VIII C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkyl arbitrarily substituted with R 16 (wherein R 16 is cyano, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 haloalkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 haloalkylsulfonyl, C 1 -C 6 alkylcarbonyl, —C(O)OR 28 , —C(O)NHR 29 , —C(O)N(R 29 )R 28 ,
  • R 1 -IX C 1 -C 6 haloalkyl, C 1 -C 6 alkyl arbitrarily substituted with R 16 (wherein R 16 is cyano, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 haloalkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 haloalkylsulfonyl, C 1 -C 6 alkylcarbonyl, —C(O)OR 28 , —C(O)NHR 29 , —C(O)N(R 29 )R 28 , —C(S)NH 2 ,
  • R 1 -X C 1 -C 8 haloalkyl, C 1 -C 6 alkyl arbitrarily substituted with R 16 (wherein R 16 is C 3 -C 6 cycloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl, —C(O)NH 2 , —C(O)NHR 28 , —C(S)NH 2 , —C(R 31 ) ⁇ NOH, —C(R 31 ) ⁇ NOR 30 , D-1 to D-4, D-8 to D-38, D-47 to D-54, E-4 to E-7, E-10, E-11 or E-32, R 28 is C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 8 alkenyl or C 3
  • R 1 -XI C 1 -C 6 alkyl and phenyl C 1 -C 6 alkyl.
  • R 1 -XII C 1 -C 8 alkyl, C 1 -C 8 alkyl arbitrarily substituted with R 16 (wherein R 16 is halogen atom, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, phenyl, phenyl substituted with (Z) p1 , D-1 to D-4, D-8 to D-42, D-47 to D-55, E-4 to E-12, E-14, E-16 to E-19, E-21 to E-23, E-26 to E-35, E-40 to E-45, E-48, M-2, M-3, M-5, M-8 to M-10, M-14, M-15 or M-16), C 3 -C 8 cycloalkyl and C 3 -C 8 halocycloalkyl.
  • R 1 -XIII C 1 -C 8 alkyl arbitrarily substituted with —OR 25 wherein R 25 is hydrogen atom, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, —C(O)R 33 , —C(O)OR 33 , —C(O)NHR 34 , —C(O)N(R 34 )R 33 , —C(S)NHR 34 , —C(S)N(R 34 )R 33 , —S(O) 2 R 33 , —S(O) 2 N(R 34 )R 33 , di(C 1 -C 6 alkyl)thiophosphoryl, phenyl or phenyl substituted with (Z) p1 , R 33 is C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, phenyl
  • R 1 -XIV C 1 -C 8 alkyl arbitrarily substituted with —N(R 26 )R 25 wherein R 25 is C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, —C(O)R 33 , —C(O)OR 33 , —C(O)SR 33 , —C(O)NHR 34 , —C(O)N(R 34 )R 33 , —C(S)R 33 , —C(S)OR 33 , —C(S)SR 33 , —C(S)NHR 34 , —C(S)N(R 34 )R 33 , —S(O) 2 R 33 or —S(O) 2 N(R 34 )R 33 , R 26 is hydrogen atom or C 1 -C 6 alkyl, or R 26 together with R 25 may form 4- to 6-membered ring with the nitrogen atom bonding them by forming C 3 -C 5 alkylene
  • R 1 -XV C 1 -C 8 alkyl arbitrarily substituted with —S(O) r R 27 wherein R 27 is C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, tri(C 1 -C 4 alkyl)silyl C 1 -C 4 alkyl, C 1 -C 6 alkylthio, —C(O)NHR 34 , —C(O)N(R 34 )R 33 , —C(S)NHR 34 , —C(S)N(R 34 )R 33 , phenyl, phenyl substituted with (Z) p1 , D-47 or D-50, R 33 is C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, phenyl C 1 -C 4 alkyl, phenyl C 1 -C
  • R 1 -XVI C 1 -C 8 alkyl arbitrarily substituted with R 16 wherein R 16 is cyano, —SO 2 NHR 29 , —SO 2 N(R 29 )R 28 , —CHO, —C(O)R 28 , —C(O)OR 28 , —C(O)NHR 29 , —C(O)N(R 29 )R 28 , —C(S)NHR 29 , —C(S)N(R 29 )R 28 , —C(R 31 ) ⁇ NOH, —C(R 31 ) ⁇ NOR 30 , —C( ⁇ NR 31 )OR 30 , —C( ⁇ NR 31 )SR 30 , —C( ⁇ NR 31 )N(R 30 )R 29 , —C( ⁇ NOR 31 )NHR 29 or —C( ⁇ NOR 31 )N(R 30 )R 29 , R 28 is C 1 -C 6 alkyl, C 1 -C 6
  • R 1 -XVII C 3 -C 8 alkenyl, C 3 -C 8 haloalkenyl, C 3 -C 8 alkynyl, C 3 -C 8 haloalkynyl, phenyl substituted with (Z) p1 , D-8 to D-18, D-21 to D-24, D-26 to D-40, D-42, D-45 to D-58, E-4, E-5, E-7, E-9, E-23 to E-25, E-27, E-28, E-30, E-31 and E-34.
  • R 1 -XVIII —N(R 20 )R 19 wherein R 19 is C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl C 1 -C 6 alkyl, phenyl C 1 -C 6 alkyl, phenyl C 1 -C 6 alkyl substituted with (Z) p1 , C 3 -C 6 cycloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, —C(O)R 28 , —C(O)OR 28 , —C(O)NHR 29 , —C(O)N(R 29 )R 28 , —C(S)NHR 29 , —C(S)N(R 29 )R 28 , C 1 -C 6 alkylsulfonyl, C 1 -C 6 halo
  • the substituent R 2 includes for example the following groups.
  • R 2 -I hydrogen atom
  • R 2 -II C 1 -C 6 alkyl, C 1 -C 6 haloalkyl and C 3 -C 6 cycloalkyl.
  • R 2 -III C 1 -C 4 alkoxy C 1 -C 4 alkyl, C 1 -C 4 alkylthio C 1 -C 4 alkyl and cyano C 1 -C 6 alkyl.
  • R 2 -IV C 3 -C 6 alkenyl and C 3 -C 6 alkynyl.
  • R 2 -V —OH, C 1 -C 6 alkoxy, C 1 -C 6 alkylcarbonyloxy, C 1 -C 6 alkoxycarbonyloxy and C 1 -C 6 alkylsulfonyloxy.
  • R 2 -VI C 1 -C 6 haloalkylthio, phenylthio, phenylthio substituted with (Z) p1 and —SN(R 18 )R 17 wherein R 17 is C 1 -C 6 alkyl, C 1 -C 6 alkoxycarbonyl C 1 -C 4 alkyl or C 1 -C 6 alkoxycarbony, R 18 is C 1 -C 6 alkyl or benzyl.
  • R 2 -VII —NHR 20 (wherein R 20 is hydrogen atom, C 1 -C 6 alkyl, —CHO, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl or C 1 -C 6 alkylsulfonyl), —N ⁇ CHR 19b and —N ⁇ C(R 19b )R 19a wherein R 19a is C 1 -C 6 alkyl, R 19b is hydrogen atom or C 1 -C 6 alkyl.
  • R 2 -VIII —C(O)R 9 , —C(O)OR 9 , —C(O)SR 9 , —C(S)OR 9 , —C(S)SR 9 (wherein R 9 is C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl C 1 -C 4 alkyl, C 1 -C 6 alkoxy C 1 -C 4 alkyl, C 1 -C 6 alkylthio C 1 -C 4 alkyl, cyano C 1 -C 6 alkyl, phenyl C 1 -C 4 alkyl, C 3 -C 8 cycloalkyl, C 3 -C 8 halocycloalkyl, C 3 -C 6 alkenyl or C 3 -C 6 alkynyl) and C 1 -C 6 alkylsulfonyl.
  • R 9 is C 1 -C 6 alkyl
  • R 2 -IX 3- to 7-membered ring that R 2 forms together with R 1 is aziridine, azetidine, pyrrolidine, oxazolidine, thiazoridine, piperidine, morpholine, thiomorpholine and homopiperidine.
  • R 2 -X hydrogen atom, C 1 -C 6 alkyl, C 1 -C 4 alkoxy C 1 -C 4 alkyl, C 1 -C 4 alkylthio C 1 -C 4 alkyl, cyano C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, —OH, C 1 -C 6 alkylcarbonyloxy, C 1 -C 6 alkylsulfonyloxy, —NH 2 , —C(O)R 9 , —C(O)OR 9 , —C(O)SR 9 , —C(S)OR 9 and —C(S)SR 9 wherein R 9 is C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl C 1 -C 4 alkyl, C 1 -C 6 alk
  • the substituent R 3 includes for example the following groups.
  • R 3 -I C 1 -C 6 haloalkyl and C 3 -C 8 halocycloalkyl.
  • R 3 -II C 1 -C 6 alkyl, C 3 -C 8 cycloalkyl, E-4 to E-7, E-23 to E-27 and E-28.
  • R 3 -III C 1 -C 4 alkoxy C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy C 1 -C 4 haloalkyl, C 1 -C 4 alkylthio C 1 -C 4 haloalkyl, C 1 -C 4 alkylsulfinyl C 1 -C 4 haloalkyl, C 1 -C 4 alkylsulfonyl C 1 -C 4 haloalkyl, C 1 -C 4 haloalkylthio C 1 -C 4 haloalkyl, C 1 -C 4 haloalkylsulfinyl C 1 -C 4 haloalkyl, C 1 -C 4 haloalkylsulfonyl C 1 -C 4 haloalkyl and cyano C 1 -C 6 haloalkyl.
  • R 3 -IV C 3 -C 6 cycloalkyl C 1 -C 4 alkyl, C 3 -C 6 halocycloalkyl C 1 -C 4 alkyl, C 1 -C 4 alkoxy C 1 -C 4 alkyl, C 1 -C 4 haloalkoxy C 1 -C 4 alkyl, C 1 -C 4 alkylthio C 1 -C 4 alkyl, C 1 -C 4 alkylsulfinyl C 1 -C 4 alkyl, C 1 -C 4 alkylsulfonyl C 1 -C 4 alkyl, C 1 -C 4 haloalkylthio C 1 -C 4 alkyl, C 1 -C 4 haloalkylsulfinyl C 1 -C 4 alkyl, C 1 -C 4 haloalkylsulfonyl C 1 -C 4 alkyl and cyano C 1 -C 6 alky
  • R 3 —V C 1 -C 6 haloalkyl, C 1 -C 4 alkoxy C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy C 1 -C 4 haloalkyl, C 1 -C 4 alkylthio C 1 -C 4 haloalkyl, C 1 -C 4 haloalkylthio C 1 -C 4 haloalkyl, cyano C 1 -C 6 haloalkyl and C 3 -C 8 halocycloalkyl.
  • R 3 -VI C 1 -C 6 haloalkyl.
  • R 3 -VII C 1 -C 6 alkyl arbitrarily substituted with two or more arbitrary halogen atoms.
  • each group showing the scope of each substituent in the compounds included in the present invention can be arbitrarily combined one another, and all combination thereof falls within the scope of the present invention.
  • Examples of the combination of the scope of X, Y and R 1 include for example the combination showin in Table 1.
  • the combination of Table 1 is for illustrative purposes, and the present invention is not limited thereto.
  • the compounds of the present invention can be produced for example according to the methods mentioned below.
  • the compound of formula (1-1) wherein A 1 , A 2 , A 3 , G, X, Y, R 1 , R 2 , R 3 , m and n are as defined above that is the compound of formula (1) wherein W is oxygen atom can be obtained by reacting the compound of formula (5) wherein A 1 , A 2 , A 3 , G, X, Y, R 3 , m and n are as defined above with the compound of formula (6) wherein R 1 and R 2 are as defined above by use of a condensation agent, optionally by using a solvent inactive for the reaction, optionally in the presence of a base.
  • reaction substrates can be used in an amount of 1 to 100 equivalents of the compound of formula (6) based on 1 equivalent of the compound of formula (5).
  • the condensation agent is not specifically limited if it is a compound used for ordinary amide synthesis, but it is for example Mukaiyama agent (2-chloro-N-methylpyridinium iodide), DCC (1,3-dicyclohexyl carbodiimide), WSC (1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride), CDI (carbonyl diimidazole), dimethylpropynyl sulfonium bromide, propagyl triphenyl phosphonium bromide, DEPC (diethyl phosphorocyanidate) or the like, and can be used in an amount of 1 to 4 equivalents based on the compound of formula (5).
  • Mukaiyama agent (2-chloro-N-methylpyridinium iodide), DCC (1,3-dicyclohexyl carbodiimide), WSC (1-ethyl-3-(3-dimethylaminoprop
  • the solvent is not specifically limited if it dose not inhibit the progress of the reaction, but it includes for example aromatic hydrocarbons such as benzene, toluene, xylene or the like, aliphatic hydrocarbons such as hexane, heptane or the like, alicyclic hydrocarbons such as cyclohexane or the like, aromatic halogenated hydrocarbons such as chlorobenzene, dichlorobenzene or the like, aliphatic halogenated hydrocarbons such as dichloro methane, chloroform, carbon tetrachloride, 1,2-dichloroethane, 1,1,1-trichloroethane, trichloroethylene, tetrachloroethylene or the like, ethers such as diethyl ether, 1,2-dimethoxyethane, tetrahydrofuran, 1,4-dioxane or the like, esters such as ethyl ether, 1,2-dimethoxy
  • alkali metal hydroxides such as sodium hydroxide, potassium hydroxide or the like
  • alkali metal carbonates such as sodium carbonate, potassium carbonate or the like
  • alkali metal bicarbonates such as sodium hydrogen carbonate, potassium hydrogen carbonate or the like
  • organic bases such as triethyamine, tributylamine, N,N-dimethylaniline, pyridine, 4-(dimethylamino)pyridine, imidazole, 1,8-diazabicyclo[5.4.0]-7-undecene, and the like
  • organic bases such as triethyamine, tributylamine, N,N-dimethylaniline, pyridine, 4-(dimethylamino)pyridine, imidazole, 1,8-diazabicyclo[5.4.0]-7-undecene, and the like
  • imidazole 1,8-diazabicyclo[5.4.0]-7-undecene, and the like
  • the reaction temperature may be an arbitrary temperature ranging from ⁇ 60° C. to the reflux temperature of a reaction mixture
  • the reaction time may be an arbitrary time ranging from 5 minutes to 100 hours although it varies depending on the concentration of the reaction substrates or the reaction temperature.
  • the reaction by using 1 to 20 equivalents of the compound of formula (6) and 1 to 4 equivalent of the condensation agent such as WSC (1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride), CDI (carbonyl diimidazole) or the like based on 1 equivalent of the compound of formula (5), optionally in the presence of 1 to 4 equivalents of a base such as potassium carbonate, triethylamine, pyridine, 4-(dimethylamino)pyridine or the like, without solvent or in a solvent such as dichloromethane, chloroform, diethyl ether, tetrahydrofurane, 1,4-dioxane or the like, at a temperature ranging from 0° C. to the reflux temperature of these solvents for 10 minutes to 24 hours.
  • the condensation agent such as WSC (1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride), CD
  • the compound of formula (1-1) according to the present invention can be also synthesized by reacting the compound of formula (7) wherein A 1 , A 2 , A 3 , G, X, Y, R 3 , m and n are as defined above, J 1 is chlorine atom, bromine atom, C 1 -C 4 alkylcarbonyloxy (for example pivaloyloxy), C 1 -C 4 alkoxycarbonyloxy (for example isobutyloxycarbonyloxy) or azolyl (for example imidazol-1-yl) that can be synthesized according to a known method disclosed in documents from the compound of formula (5), for example a method by reacting with a chlorinating agent such as thionyl chloride, phosphorus pentachloride or oxalyl chloride, a method by reacting with a organic acid halide such as pivaloyl chloride or isobutyl chlorformate, etc.
  • a chlorinating agent such as
  • reaction substrates can be used in an amount of 1 to 50 equivalents of the compound of formula (6) based on 1 equivalent of the compound of formula (7).
  • the solvent is not specifically limited if it dose not inhibit the progress of the reaction, but it includes for example aromatic hydrocarbons such as benzene, toluene, xylene or the like, aliphatic hydrocarbons such as hexane, heptane or the like, alicyclic hydrocarbons such as cyclohexane or the like, aromatic halogenated hydrocarbons such as chlorobenzene, dichlorobenzene or the like, aliphatic halogenated hydrocarbons such as dichloro methane, chloroform, carbon tetrachloride, 1,2-dichloroethane, 1,1,1-trichloroethane, trichloroethylene, tetrachloroethylene or the like, ethers such as diethyl ether, 1,2-dimethoxyethane, tetrahydrofuran, 1,4-dioxane or the like, esters such as ethyl ether, 1,2-dimethoxy
  • alkali metal hydroxides such as sodium hydroxide, potassium hydroxide or the like
  • alkali metal carbonates such as sodium carbonate, potassium carbonate or the like
  • alkali metal bicarbonates such as sodium hydrogen carbonate, potassium hydrogen carbonate or the like
  • organic bases such as triethyamine, tributylamine, N,N-dimethylaniline, pyridine, 4-(dimethylamino)pyridine, imidazole, 1,8-diazabicyclo[5.4.0]-7-undecene, and the like can be used in an amount of 1 to 4 equivalents based on the compound of formula (7).
  • the reaction temperature may be an arbitrary temperature ranging from ⁇ 60° C. to the reflux temperature of a reaction mixture
  • the reaction time may be an arbitrary time ranging from 5 minutes to 100 hours although it varies depending on the concentration of the reaction substrates or the reaction temperature.
  • a base such as potassium carbonate, triethylamine, pyridine, 4-(dimethylamino)pyridine or the like
  • a solvent such as dichloromethane, chloroform, diethyl ether, tetrahydrofurane, 1,4-dioxane, ethyl acetate, acetonitrile or the like, at a temperature ranging from 0° C. to the reflux temperature of these solvents for 10 minutes to 24 hours.
  • Halogenating agents include for example N-halosuccinimides such as N-chlorosuccinimide, N-bromosuccinimide or the like, hypohalogenous acid alkali metal salts such as sodium hypochlorite or the like, hypohalogenous acid esters such as hypochlorous acid-t-butyl ester or the like, simple substance halogens such as chlorine gas or the like, and it can be used in an amount of 1 to 10 equivalents based on the compound of formula (8).
  • N-halosuccinimides such as N-chlorosuccinimide, N-bromosuccinimide or the like
  • hypohalogenous acid alkali metal salts such as sodium hypochlorite or the like
  • hypohalogenous acid esters such as hypochlorous acid-t-butyl ester or the like
  • simple substance halogens such as chlorine gas or the like
  • the solvent is not specifically limited if it dose not inhibit the progress of the reaction, but it includes for example aromatic hydrocarbons such as benzene, toluene, xylene or the like, aliphatic hydrocarbons such as hexane, heptane or the like, alicyclic hydrocarbons such as cyclohexane or the like, aromatic halogenated hydrocarbons such as chlorobenzene, dichlorobenzene or the like, aliphatic halogenated hydrocarbons such as dichloro methane, chloroform, carbon tetrachloride, 1,2-dichloroethane, 1,1,1-trichloroethane, trichloroethylene, tetrachloroethylene or the like, ethers such as diethyl ether, 1,2-dimethoxyethane, tetrahydrofuran, 1,4-dioxane or the like, esters such as ethyl ether, 1,2-dimethoxy
  • the reaction temperature may be an arbitrary temperature ranging from ⁇ 60° C. to the reflux temperature of a reaction mixture
  • the reaction time may be an arbitrary time ranging from 5 minutes to 24 hours although it varies depending on the concentration of the reaction substrates or the reaction temperature.
  • the compounds of formula (1) wherein A 1 , A 2 , A 3 , G, W, X, Y, R 1 , R 2 , R 3 , m and n are as defined above according to the present invention can be obtained by reacting the compound of formula (9) with the compound of formula (10) wherein G, X, R 3 and m are as defined above in the presence of a base optionally by use of a solvent inactive for the reaction.
  • reaction substrates can be used in an amount of 1 to 5 equivalents of the compound of formula (10) based on 1 equivalent of the compound of formula (9).
  • the used base includes for example alkali metal hydroxides such as sodium hydroxide, potassium hydroxide or the like, alkali metal carbonates such as sodium carbonate, potassium carbonate or the like, alkali metal bicarbonates such as sodium hydrogen carbonate, potassium hydrogen carbonate or the like, organic bases such as triethyamine, tributylamine, N,N-dimethylaniline, pyridine, 4-(dimethylamino)pyridine, imidazole, 1,8-diazabicyclo[5.4.0]-7-undecene, and the like can be used in an amount of 1 to 5 equivalents based on the compound of formula (9).
  • the solvent is not specifically limited if it dose not inhibit the progress of the reaction, but it includes for example aromatic hydrocarbons such as benzene, toluene, xylene or the like, aliphatic hydrocarbons such as hexane, heptane or the like, alicyclic hydrocarbons such as cyclohexane or the like, aromatic halogenated hydrocarbons such as chlorobenzene, dichlorobenzene or the like, aliphatic halogenated hydrocarbons such as dichloro methane, chloroform, carbon tetrachloride, 1,2-dichloroethane, 1,1,1-trichloroethane, trichloroethylene, tetrachloroethylene or the like, ethers such as diethyl ether, 1,2-dimethoxyethane, tetrahydrofuran, 1,4-dioxane or the like, esters such as ethyl ether, 1,2-dimethoxy
  • the reaction temperature may be an arbitrary temperature ranging from ⁇ 60° C. to the reflux temperature of a reaction mixture
  • the reaction time may be an arbitrary time ranging from 5 minutes to 100 hours although it varies depending on the concentration of the reaction substrates or the reaction temperature.
  • the compound of formula (9) can be obtained for example by carrying out the reaction by using 1 to 2 equivalents of a halogenating agent such as N-chlorosuccinimide, sodium hypochlorite aqueous solution, hypochlorous acid-t-butyl ester, chlorine gas or the like based on 1 equivalent of the compound of formula (8) in a solvent such as dichloromethane, chloroform, 1,2-dimethoxyethane, tetrahydrofurane, 1,4-dioxane, N,N-dimethylformamide or the like, at a temperature ranging from 0° C. to the reflux temperature of these solvents for 10 minutes to 2 hours.
  • a halogenating agent such as N-chlorosuccinimide, sodium hypochlorite aqueous solution, hypochlorous acid-t-butyl ester, chlorine gas or the like based on 1 equivalent of the compound of formula (8) in a solvent such as dichloromethane, chloroform,
  • the compound of formula (1-1) wherein A 1 , A 2 , A 3 , G, X, Y, R 1 , R 3 , m and n are as defined above and R 2 has the same meaning defined above excluding hydrogen atom according to the present invention that is the compound of formula (1) wherein W is oxygen atom can be obtained by reacting the compound of formula (1-2) wherein A 1 , A 2 , A 3 , G, X, Y, R 1 , R 3 , m and n are as defined above that is the compound of formula (1) wherein W is oxygen atom and R 2 is hydrogen atom with the compound of formula (11) wherein R 2 has the same meaning defined above excluding hydrogen atom, J 3 is a good leaving group such as chlorine atom, bromine atom, iodine atom, C 1 -C 4 alkylcarbonyloxy (for example pivaloyloxy), C 1 -C 4 alkylsulfonate (for example methane sulfonyloxy),
  • reaction substrates can be used in an amount of 1 to 50 equivalents of the compound of formula (11) based on 1 equivalent of the compound of formula (1-2).
  • the solvent is not specifically limited if it dose not inhibit the progress of the reaction, but it includes for example aromatic hydrocarbons such as benzene, toluene, xylene or the like, aliphatic hydrocarbons such as hexane, heptane or the like, alicyclic hydrocarbons such as cyclohexane or the like, aromatic halogenated hydrocarbons such as chlorobenzene, dichlorobenzene or the like, aliphatic halogenated hydrocarbons such as dichloro methane, chloroform, carbon tetrachloride, 1,2-dichloroethane, 1,1,1-trichloroethane, trichloroethylene, tetrachloroethylene or the like, ethers such as diethyl ether, 1,2-dimethoxyethane, tetrahydrofuran, 1,4-dioxane or the like, esters such as ethyl ether, 1,2-dimethoxy
  • alkali metal hydride such as sodium hydride, potassium hydride or the like
  • alkali metal hydroxides such as sodium hydroxide, potassium hydroxide or the like
  • alkali metal alkoxides such as sodium ethoxide, potassium t-butoxide or the like
  • alkali metal amides such as lithium diisopropylamide, lithium hexamethyl disilazane, sodium amide or the like
  • organic metal compounds such as t-butyl lithium or the like
  • alkali metal carbonates such as sodium carbonate, potassium carbonate, sodium hydrogen carbonate or the like
  • organic bases such as triethyamine, tributylamine, N,N-dimethylaniline, pyridine, 4-(dimethylamino)pyridine, imidazole, 1,8-diazabicyclo[5.4.0]-7-undecene, and the like
  • organic bases such as triethyamine, tributylamine, N,N-dimethyl
  • the reaction temperature may be an arbitrary temperature ranging from ⁇ 60° C. to the reflux temperature of a reaction mixture
  • the reaction time may be an arbitrary time ranging from 5 minutes to 100 hours although it varies depending on the concentration of the reaction substrates or the reaction temperature.
  • the reaction by using 1 to 10 equivalents of the compound of formula (11) based on 1 equivalent of the compound of formula (1-2), in a polar solvent such as tetrahydrofurane, 1,4-dioxane, acetonitrile, N,N-dimethylformamide or the like, optionally in the presence of 1 to 3 equivalents of a base such as sodium hydride, potassium t-butoxide, potassium hydroxide, potassium carbonate, triethylamine, pyridine or the like, based on 1 equivalent of the compound of formula (1-2), at a temperature ranging from 0 to 90° C. for 10 minutes to 24 hours.
  • a polar solvent such as tetrahydrofurane, 1,4-dioxane, acetonitrile, N,N-dimethylformamide or the like
  • a base such as sodium hydride, potassium t-butoxide, potassium hydroxide, potassium carbonate, triethylamine, pyridine or the like
  • the compound of formula (1-3) wherein A 1 , A 2 , A 3 , G, X, Y, R 1 , R 2 , R 3 , m and n are as defined above according to the present invention that is the compound of formula (1) wherein W is sulfur atom can be obtained by reacting the compound of formula (1-1) wherein A 1 , A 2 , A 3 , G, X, Y, R 1 , R 2 , R 3 , m and n are as defined above according to the present invention that is the compound of formula (1) wherein W is oxygen atom with a sulfurizing agent such as diphosphorus pentasulfide, diphosphorus pentasulfide-HMDO (hexamethyldisiloxane), Lawesson's Reagent (2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide), optionally by using a solvent inactive for the reaction, optionally
  • reaction substrates can be used in an amount of 1 to 50 equivalents of the sulfurizing agent based on 1 equivalent of the compound of formula (1-1).
  • the solvent is not specifically limited if it dose not inhibit the progress of the reaction, but it includes for example aromatic hydrocarbons such as benzene, toluene, xylene or the like, aliphatic hydrocarbons such as hexane, heptane or the like, alicyclic hydrocarbons such as cyclohexane or the like, aromatic halogenated hydrocarbons such as chlorobenzene, dichlorobenzene or the like, aliphatic halogenated hydrocarbons such as dichloro methane, chloroform, carbon tetrachloride, 1,2-dichloroethane, 1,1,1-trichloroethane, trichloroethylene, tetrachloroethylene or the like, ethers such as diethyl ether, 1,2-dimethoxyethane, tetrahydrofuran, 1,4-dioxane or the like, amines such as triethyl
  • a base is not necessarily required.
  • alkali metal carbonates such as sodium carbonate, potassium carbonate, sodium hydrogen carbonate or the like
  • organic bases such as triethyamine, tributylamine, N,N-dimethylaniline, pyridine, 4-(dimethylamino)pyridine, imidazole, 1,8-diazabicyclo[5.4.0]-7-undecene, and the like can be used in an amount of 1 to 10 equivalents based on the compound of formula (1-1).
  • the reaction temperature may be an arbitrary temperature ranging from 0° C. to the reflux temperature of a reaction mixture
  • the reaction time may be an arbitrary time ranging from 5 minutes to 100 hours although it varies depending on the concentration of the reaction substrates or the reaction temperature.
  • a sulfurizing agent such as diphosphorus pentasulfide, diphosphorus pentasulfide-HMDO, Lawesson's Reagent or the like, based on 1 equivalent of the compound of formula (1-1), optionally in the presence of 1 to 4 equivalents of a base such as sodium hydrogen carbonate, triethyamine, pyridine or the like, in a solvent such as benzene, toluene, chlorobenzene, dichloromethane, chloroform, 1,2-dimethoxyethane, tetrahydrofurane, 1,4-dioxane, HMPA or the like, at a temperature ranging from room temperature to the reflux temperature of the reaction mixture for 10 minutes to 50 hours, or in a solvent amount of pyridine at a temperature of 80° C. to the reflux temperature of the reaction mixture for 1 to 3 hours.
  • a sulfurizing agent such as diphosphorus pentasulfide, diphosphorus pentasulfide-HMDO,
  • the aimed compound of the present invention can be obtained by subjecting the reaction mixture after the completion of the reaction to ordinary post-treatment such as a direct concentration, or a concentration after dissolving in an organic solvent and washing with water or a concentration after placing in ice water and extracting with an organic solvent.
  • ordinary post-treatment such as a direct concentration, or a concentration after dissolving in an organic solvent and washing with water or a concentration after placing in ice water and extracting with an organic solvent.
  • a purification when a purification is required, it can be separated and purified by an arbitrary purification process such as recrystallization, column chromatograph, thin layer chromatograph, liquid chromatograph collection or the like.
  • the compound of formula (5) used in Production Method A can be synthesized as follows, for example.
  • the compound of formula (5) wherein A 1 , A 2 , A 3 , G, X, Y, R 3 , m and n are as defined above can be obtained by reacting the compound of formula (12) wherein A 1 , A 2 , A 3 , G, X, Y, R 3 , m and n are as defined above, J 4 is bromine atom, iodine atom, halosulfonyloxy (for example fluorosulfonyloxy), C 1 -C 4 haloalkylsulfonyloxy (for example trifluoromethane sulfonyloxy) or arylsulfonyloxy (for example benzenesulfonyloxy) according to a known method disclosed in documents, for example by CO insertion reaction by use of a transition metal catalyst such as palladium or the like stated in J. Org. Chem., 1999, vol. 64, p. 6921 or the like, or by
  • the compound of formula (5) can be obtained by subjecting the compound of formula (12) to a reaction according to a reaction condition for CO insertion reaction by use of a transition metal catalyst such as palladium or the like stated in J. Org. Chem., 1974, vol. 39, p. 3318 or the like to convert the compound of formula (13) wherein A 1 , A 2 , A 3 , G, X, Y, R 3 , m and n are as defined above, R b is C 1 -C 6 alkyl such as methyl, ethyl or the like, and then hydrolizing according to an ordinary ester hydrolysis disclosed in documents, for example a reaction condition stated in Angew. Chem., 1951, vol. 63, p. 329, J. Am. Chem. Soc., 1929, vol. 51, p. 1865 or the like.
  • a transition metal catalyst such as palladium or the like stated in J. Org. Chem., 1974, vol. 39, p. 3318
  • the compounds of formula (8) used in Production Method B can be synthesized as follows, for example.
  • the compound of formula (8) wherein A 1 , A 2 , A 3 , W, Y, R 1 , R 2 and n are as defined above can be easily synthesized by reacting the compound of formula (14) wherein A 1 , A 2 , A 3 , W, Y, R 1 , R 2 and n are as defined above with hydroxyamine or the salt thereof according to known methods disclosed in documents, for example the method stated in J. Med. Chem., 2001, vol. 44, p. 2308 or the like.
  • the compounds of formula (10) used in Production Method B can be synthesized as follows, for example.
  • the compound of formula (10) wherein G, X, R 3 and m are as defined above can be obtained by reacting the known compound of formula (15) wherein G, X and m are as defined above, J 5 is bromine atom, iodine atom, C 1 -C 4 haloalkylsulfonyloxy (for example trifluoromethanesulfonyloxy), —B(OH) 2 , 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl, —Si(OEt) 3 , —ZnCl, —ZnBr or —ZnI, etc.
  • J 5 is bromine atom, iodine atom, C 1 -C 4 haloalkylsulfonyloxy (for example trifluoromethanesulfonyloxy), —B(OH) 2 , 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-y
  • J 6 is halogen atom such as bromine atom, iodine atom or the like, or —B(OH) 2 according to an ordinary crosscoupling reaction by use of a transition metal catalyst such as palladium or the like disclosed in documents, for example a reaction condtioin stated in J. Org. Chem., 1991, vol. 56, p. 7336, Tetrahedron Lett., 2001, vol. 42, p. 4083, or the like.
  • the compounds of formula (10) can be obtained by reacting the compound of formula (17) wherein G, X, R 3 and m are as defined above according to a reaction of converting carbonyl to olefine disclosed in documents, for example areaction condition stated in J. Org. Chem., 1986, vol. 51, p. 5252 and 1994, vol. 59, p. 2898, Synthesis, 1991, p. 29, Tetrahedron Lett., 1985, vol. 26, p. 5579 or the like.
  • Some of the compounds of formula (11) used in Production method C are known compounds, and a part thereof is commercially available. Also, the compounds other than the above-mentioned compounds can be easily synthesized according to methods disclosed in documents, for example a method stated in Chem. Lett., 1976, p. 373, J. Am. Chem. Soc., 1964, vol. 86, p. 4383, J. Org. Chem., 1976, vol. 41, p. 4028 and 1978, vol. 43, p. 3244, Org. Synth., 1988, Corrective vol. 6, p. 101, Tetrahedron Lett., 1972, p. 4339, GB 2,161,802, EP 0,051,273 or the like.
  • the compounds of formula (12) can be synthesized as follows, for example.
  • the compounds of formula (12) wherein A 1 , A 2 , A 3 , G, X, Y, R 3 , m, n and J 4 are as defined above can be obtained by halogenating the compound of formula (18) wherein A 1 , A 2 , A 3 , Y, n and J 4 are as defined above under a condition similar to that of Production Method B to obtain the compound of formula (19) wherein A 1 , A 2 , A 3 , Y, n, J 3 and J 4 are as defined above, and then reacting it with the compound of formula (10) wherein G, X, R 3 and m are as defined above.
  • the compound of formula (18) can be easily synthesized by use of the corresponding known substituted aromatic aldehyde similarly to the process described in Reaction Scheme 2.
  • the compound of formula (14) can be synthesized for example acccording to Reaction Scheme 5 or Reaction Scheme 6.
  • the compounds of formula (14) wherein A 1 , A 2 , A 3 , W, Y, R 1 , R 2 and n are as defined above can be obtained by subjecting the compound of formula (20) wherein A 1 , A 2 , A 3 , W, Y, R 1 , R 2 , n and J 4 are as defined above to CO insertion reaction according to known methods disclosed in documents, for example the reaction by use of a transition metal catalyst such as palladium or the like in the presence of hydride source such as formic acid or the like stated in Bull. Chem. Soc. Jpn., 1994, vol. 67, p. 2329, J. Am. Chem. Soc., 1986, vol. 108, p. 452, or the like.
  • the compounds of formula (14-1) wherein A 1 , A 2 , A 3 , Y, R 1 , R 2 and n are as defined above that are the compounds of formula (14) wherein W is oxygen atom can be synthesized by reacting the known compound of formula (21) wherein A 1 , A 2 , A 3 , Y and n are as defined above with the compound of formula (6) wherein R 1 and R 2 are as defined above by use of the method similar to Production Method A.
  • the compounds of formula (17) wherein X, R 3 and m are as defined above, G is benzene ring can be obtained by reacting the known compound of formula (23) wherein X and m are as defined above, G is benzene ring with the known compound of formula (24) wherein R 3 is as defined above, J 7 is a leaving group such as halogen atom, trifluoromethanesulfonyloxy, 2-pyridyloxy or the like, or the known compound of formula (25) wherein R 3 is as defined above according to a general acylating reaction of aromatic ring disclosed in documents, for example a method stated in Chem. Lett., 1990, p. 783, J. Org. Chem., 1991, vol. 56, p. 1963 or the like.
  • the compounds of formula (20-1) wherein A 1 , A 2 , A 3 , Y, R 1 , R 2 , n and J 4 are as defined above that are the compounds of formula (20) wherein W is oxygen atom can be obtained by reacting the known compound of formula (28) wherein A 1 , A 2 , A 3 , Y, n and J 4 are as defined above with the compound of formula (6) wherein R 1 and R 2 are as defined above by use of the method similar to Production Method A.
  • the compounds of formula (20-2) wherein A 1 , A 2 , A 3 , Y, R 1 , R 2 , n and J 5 are as defined above that are the compounds of formula (20) wherein W is sulfur atom can be obtained by reacting the compound of formula (20-1) wherein A 1 , A 2 , A 3 , Y, R 1 , R 2 , n and J 4 are as defined above that are the compounds of formula (20) wherein W is oxygen atom with a sulfurizing agent such as diphosphorus pentasulfide, diphosphorus pentasulfide-HMDO (hexamethyldisiloxane), Lawesson's Reagent (2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide) under a condition similar to that of Production Method D.
  • a sulfurizing agent such as diphosphorus pentasulfide, diphosphorus pentasulf
  • each production intermediate that is a starting compound in Production Method A to Produciton Method C can be obtained by carrying out normal post-treatments.
  • each production intermediate produced by the above-mentioned methods can be used for the following reaction step as such without isolation or purification.
  • the active compounds included in the present invention concretely include for example the compounds shown in Tables 2 and 3.
  • the compounds that can be used as novel production intermediates for producing the active compounds included in the present invention concretely include for example the compounds shown in Tables 4 to 6.
  • the compounds shown in Tables 2 to 6 are for purposes of illustration and the present invention is not limited thereto.
  • aliphatic heterocyclic rings of E-4-a to E-43b are the following structures, respectively
  • the indication “[CH 2 (E-10b)CH 3 ]” means 2-methyl-1,3-dioxolan-2-yl methyl
  • the indication “[CH 2 (E-8a)CH 3 ]” means N-methylpyrrolidin-2-yl methyl.
  • partially saturated heterocyclic rings of M-2a to M-16a are the following structures, respectively
  • the compounds of the present invention can effectively control in a low concentration so-called agricultural insects injuring agricultural and horticultural crops and trees, so-called domestic animal pests parasitizing domestic animals and domestic fowls, so-called hygienic pests having an adverse affect on human being's environment such as houses, insects as so-called stored grain insects injuring grains and the like stored in storehouses, and any pests of acarids, crustaceans, mollusks and nematodes generating in the similar scenes.
  • insects, acarids, crustaceans, mollusks and nematodos that the compounds of the present invention can control concretely include for example the followings: Lepidoptera insects, such as Adoxophyes honmai, Adoxophyes orana faciata, Archips breviplicanus, Archips fuscocupreanus, Grapholita molesta, Homona magnanima, Leguminivora glycinivorella, Matsumuraeses phaseoli, Pandemis heparana, Bucculatrix pyrivorella, Lyonetia clerkella, Lyonetia prunifoliella malinella, Caloptilia theivora, Phyllonorycter ringoniella, Phyllocnistis citrella, Acrolepiopsis sapporensis, Acrolepiopsis suzukiella, Plutella xylostella, Stathmopoda candidssa, Helcys
  • the endo-parasites of domestic animals, domestic fowls, pets and the like that the compounds of the present invention can control concretely include for example the followings:
  • Nematodes such as Haemonchus, Trichostrongylus, Ostertagia, Nematodirus, Cooperia, Ascaris, Bunostomum, Oesophagostomum, Chabertia, Trichuris, Storongylus, Trichonema, Dictyocaulus, Capillaria, Heterakis, Toxocara, Ascaridia, Oxyuris, Ancylostoma, Uncinaria, Toxascaris, Parascaris , or the like; Filariidae in nematodes, such as Wuchereria, Brugia, Onchoceca, Dirofilaria, Loa , or the like; Dracunculidae in nematodes, such as Deacunculus , or the like; Cestoda, such as Dipylidium caninum, Taenia taeniaeformis, Taenia solium, Taenia saginata, Hymenolepis diminuta,
  • the compounds of the present invention can effectively control pests that belong to insects such as Collembola, Dictyoptera, Orthoptera, Isoptera, Thysanoptera, Hemiptera, Lepidoptera, Coleoptera, Hymenoptera, Diptera, Isoptera and Anoplura, Acarina, Gastropoda and Nematoda, in a low concentration.
  • insects such as Collembola, Dictyoptera, Orthoptera, Isoptera, Thysanoptera, Hemiptera, Lepidoptera, Coleoptera, Hymenoptera, Diptera, Isoptera and Anoplura, Acarina, Gastropoda and Nematoda, in a low concentration.
  • the compounds of the present invention have an extremely useful charactristic that they have little adverse affect on mammals, fishes, crustaceans and useful insects (beneficial insect such as honeybee, bumblebee or the like, or, natural enemies such as Aphytis lingnanensis, Aphidius colemani, Orius strigicollis, Amblyseius californicus , or the like).
  • the compounds of the present invention can be generally mixed with a suitable solid carrier or liquid carrier, optionally along with surfactant, penetrating agent, spreading agent, thickner, anti-freezing agent, binder, anti-caking agent, disintegrating agent, anti-foaming agent, preservative, stabilizer, and the like, and can be formulated into any desired forms for practical use, such as soluble concentrates, emulsifiable concentrates, wettable powders, water soluble powders, water dispersible granules, water soluble granules, suspension concentrates, concentrated emulsions, suspoemulsions, microemulsions, dustable powders, granules, tablets and emulsifiable gels. From the viewpoint of an elimination or reduction of labor and an improvement of safety, the formulations in any desired forms described above may be included into a water-soluble bag made of water-soluble capsule or water-soluble film.
  • the solid carrier includes, for example, natural minerals such as quartz, calcite, sepiolite, dolomaite, chalk, kaolinite, pyrofilite, celicite, halocite, methahalocite, kibushi clay, gairome clay, pottery stone, zeaklite, allophane, white sand, mica, talc, bentonite, activeted earth, acid china clay, pumice, attapulgite, zeolite and diatomaceous earth, etc., calcined products of natural minerals such as calcined clay, perlite, white sand balloon (loam balloon), vermiculite, attapulgus clay and calcined diatomaceous earth, etc., inorganic salts such as magnesium carbonate, calcium carbonate, sodium carbonate, sodium hydrogen carbonate, ammonium sulfate, sodium sulfate, magnesium sulfate, diammonium hydrogen phosphate, ammonium dihydrogen phosphate and potassium
  • liquid carrier there may be mentioned, for example, aromatic hydrocarbons such as xylene, alkyl(C 9 or C 10 , etc.)benzene, phenylxylylethane and alkyl(C 1 or C 3 , etc.)naphthalene, etc., aliphatic hydrocarbons such as machine oil, normal paraffin, isoparaffin and naphthene, etc., a mixture of aromatic hydrocarbons and aliphatic hydrocarbons such as kerosene, etc., alcohols such as ethanol, isopropanol, cyclohexanol, phenoxyethanol and benzylalcohol, etc., polyvalent alcohols such as ethylene glycol, propyleneglycol, diethylene glycol, hexylene glycol, polyethylene glycol and polypropyleneglycol, etc., ethers such as propyl cellosolve, butyl cellosolve, phenyl cellosolve, propyleneglycol
  • nonionic surfactants such as polyoxyethylene alkyl ether, polyoxyethylene alkyl (mono- or di-)phenyl ether, polyoxyethylene (mono-, di- or tri-)styrylphenyl ether, polyoxyethylene polyoxypropylene block copolymer, polyoxyethylene fatty acid (mono- or di-)ester, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, caster oil-ethylene oxide adducts, acetylene glycol, acetylene alcohol, ethylene oxide adducts of acetylene glycol, ethylene oxide adducts of acetylene alcohol and alkyl glycoside, etc., anionic surfactants such as alkyl sulfate, alkylbenzenesulfonate, lignine sulfonate, alkylsulfosuccinate, naphthalene
  • a dose of the compound of the present invention to be applied may vary depending on the place to be applied, time to be applied, method to be applied, crops to cultivate, etc., and in general, it is suitable in an amount of about 0.005 to 50 kg or so per a hectare (ha) as an amount of the effective ingredient.
  • the effective amount of the compound of the present invention together with additives for formulations can be administered through oral administration, parenteral administration such as injection (intramuscular, subcutaneous, intravenous, intraperitoneal) or the like; transdermal administration such as dipping, spray, bathing, washing, pouring-on and spotting-on, and dusting, or the like; transnasal administration.
  • parenteral administration such as injection (intramuscular, subcutaneous, intravenous, intraperitoneal) or the like
  • transdermal administration such as dipping, spray, bathing, washing, pouring-on and spotting-on, and dusting, or the like
  • transnasal administration transnasal administration.
  • the compound of the present invention can be also administered through a formed product by use of a strip, a plate, a band, a collar, an ear mark, a limb band, a labe apparatus, or the like.
  • the compound of the present invention can be formed in an arbitrary dosage form that is suited
  • the arbitrary dosage form includes solid preparations such as a dustable powder, a granule, wettable powder, a pellete, a tablet, a bolus, a capsule, a formed product containing an active compound; liquid formulations such as an injectable liquid formulation, an oral liquid formulation, a liquid formulation used on skin or in body cavity; solution preparations such as a pour-on agent, a spot-on agent, a flowable agent, an emulsifiable concentrate; semi-solid preparations such as an ointment, gel or the like.
  • solid preparations such as a dustable powder, a granule, wettable powder, a pellete, a tablet, a bolus, a capsule, a formed product containing an active compound
  • liquid formulations such as an injectable liquid formulation, an oral liquid formulation, a liquid formulation used on skin or in body cavity
  • solution preparations such as a pour-on agent, a spot-on agent, a flowable agent, an emuls
  • the solid preparations can be mainly used through oral administration or transdermal administratin by diluting with water or the like, or by environmental treatment.
  • the solid preparations can be prepared by mixing the active compound with suitable excipients and optionally auxiliary substances and converting to a desired form.
  • suitable excipients include for example inorganic substances such as carbonates, hydrogen carbonates, phosphates, aluminum oxide, silica, clay or the like, organic substances such as sugar, cellulose, milled cereal, starch or the like.
  • the injectable liquid formulation can be administered intravenously, intramuscularly and subcutaneously.
  • the injectable liquid formulation can be prepared by dissolving an acitve compound in a suitable solvent and optionally by adding an additive such as a solubilizing agent, an acid, a base, a buffering salt, an antioxidant, and a protective agent or the like.
  • Suitable solvent is for example water, ethanol, butanol, benzyl alcohol, glycerin, propylene glycol, poethylene glycol, N-methylpyrrolidone, and a mixture thereof, a physiologically permissible vegetable oil, a synthetic oil suitable for injection, or the like.
  • the solubilizing agent includes polyvinyl pyrrolidone, polyoxyethylated castor oil and polyoxyethylated sorbitan ester, or the like.
  • the protective agent includes benzyl alcohol, trichlorobutanol, p-hydroxybenzoic acid ester and n-butanol or the like.
  • the oral liquid formulation can be administered directly or after dilution. It can be prepared similarly to the injectable liquid formulation.
  • the flowable agent and the emulsifiable concentrate can be administered directly or after dilution through transdermal administration or environmental treatment.
  • the liquid formulation used on skin can be administered by pouring on, spreading, rubbing, atomizing, spraying, or dipping (dipping, bathing or washing). These liquid can be prepared similarly to the injectable liquid formulation.
  • the pour-on agent and the spot-on agent are poured or atomized on the limited spot on the skin, thereby the active compound can be penetrated into the skin and act in the whole body.
  • the pour-on agent and the spot-on agent can be prepared by dissolving, suspending or emulsifying an active ingredient in a suitable skin-fitted solvent or solvent mixture. If required, an auxiliary substance such as a surfactant, a colorant, an absorption promoting agent, an antioxidant, a light stabilizer and an adhesive, etc. may be added.
  • Suitable solvent includes water, alkanol, glycol, polyethylene glycol, polypropylene glycol, glycerin, benzyl alcohol, phenylethanol, phenoxyethanol, ethyl acetate, butyl acetate, benzyl benzoate, dipropylene glycol monomethyl ether, diethylene glycol monobutyl ether, acetone, methyl ethyl ketone, aromatic and/or aliphatic hydrocarbon, vegetable or synthetic oil, DMF, liquid paraffin, light-duty liquid paraffin, silicone, dimethylacetamide, N-methylpyrrolidone or 2,2-dimethyl-4-oxy-methylene-1,3-dioxolane.
  • the absorption promoting agent includes DMSO, isopropyl myristate, dipropylene glycol pelargonate, silicone oil, aliphatic ester, triglyceride and fatty alcohol.
  • the antioxidant includes sulfite, metabisulfite, ascorbic acid, butylhydroxytoluene, butylhydroxyanisole and tocopherol.
  • the emusifiable concentrate can be administrated orally, subcutaneously or injectably.
  • the emusifiable concentrate can be prepared by dissolving an active ingredient in a hydrophobic phase or a hydrophilic phase, and then homogenating the resulting solution with a suitable emulsifying agent optionally with further an auxiliary substance such as a colorant, an absortion promoting agent, a protective agent, an antioxidant, a light screen and a thickening agent.
  • the hydrophobic phase includes paraffin oil, silicone oil, sesame-seed oil, oil of almonds, castor oil, synthetic triglyceride, ethyl stearate, di-n-butyryl adipate, hexyl laurate, dipropylene glycol pelargonate, ester of branched short chain length aliphatic acid with saturated aliphatic acid of chain length C16 to C18, isopropyl myristate, isopropyl palmitate, capryl/caprylic acid ester of saturated fatty alcohol of chain length C12 to C18, isopropyl stearate, oleyl oleate, decyl oleate, ethyl oleate, ethyl lactate, wax-like fatty acid ester, dibutyl phthalate, diisopropyl adipate, isotridecyl alcohol, 2-octyldodecanol, cetyl
  • the hydrophilic phase includes water, propylene glycol, glycerin, sorbitol.
  • the emulsifying agent includes non-ionic surfactants such as polyoxyethylated castor oil, polyoxyethylated sorbitan mono-olefinate, sorbitan monostearate, glycerin monostearate, polyoxyethyl stearate, alkylphenol polyglycol ether; amphoteric surfactants such as di-sodium N-lauryl-iminodipropionate, lecithin or the like; anionic surfactants such as sodium lauryl sulfate, fatty alcohol sulfric acid ether, monoethanol amine salt of mono/dialkylpolyglycol orthophosphate or the like; cationic surfactants such as cetyl chloride trimethylammonium or the like.
  • non-ionic surfactants such as polyoxyethylated castor oil, polyoxyethylated sorbitan mono-olefinate, sorbitan monostearate, glycerin monoste
  • the other auxiliary substance includes carbocymethylcellulose, methylcellulose, polyacrylate, arginate, gelatin, gum arabic, polyvinyl pyrrolidone, polyvinyl alcohol, methylvinyl ether, copolymer of maleic anhydride, polyethylene glycol, wax, colloidal silica.
  • the semi-solid preparation can be administered by coating or spreading on the skin, or by introducing in body cavity.
  • the gel can be prepared by adding a thickener in an amount enough to provide a clear substance having a viscosity of ointment in a solution prepared for the injectable liquid formulation as mentioned above.
  • Compound of the present invention 0.1 to 80 parts Solid carrier 5 to 98.9 parts Surfactant 1 to 10 parts Others 0 to 5 parts As other components, there may be mentioned, for example, a non-caking agent, a decomposition preventing agent, and the like.
  • Compound of the present invention 0.1 to 30 parts Liquid carrier 45 to 95 parts Surfactant 4.9 to 15 parts Others 0 to 10 parts
  • a spreading agent for example, a spreading agent, a decomposition preventing agent, and the like.
  • Compound of the present invention 0.1 to 70 parts Liquid carrier 15 to 98.89 parts Surfactant 1 to 12 parts Others 0.01 to 30 parts As other components, there may be mentioned, for example, an antifreezing agent, a thicknening agent, and the like.
  • Compound of the present invention 0.1 to 90 parts Solid carrier 0 to 98.9 parts Surfactant 1 to 20 parts Others 0 to 10 parts As other components, there may be mentioned, for example, a binder, a decomposition preventing agent, and the like.
  • Solid carrier 10 to 99.99 parts Others 0 to 10 parts As other components, there may be mentioned, for example, a binder, a decomposition preventing agent, and the like.
  • the compound of the present invention when used as an agricultural chemicals, it may be mixed with other kinds of herbicides, various kinds of insecticides, acaricides, nematocides, fungicides, vegetable growth regulators, synergists, fertilizers, soil improvers, etc., and applied, at the time of preparing the formulation or at the time of spreading, if necessary.
  • Fungicides acibenzolar-5-methyl, acylaminobenzamide, amobam, ampropylos, anilazine, azaconazole, azoxystrobin, benalaxyl, benodanil, benomyl, benthiazole, benzamacril, binapacryl, biphenyl, bitertanol, bethoxazine, bordeaux mixture, blasticidin-S, bromoconazole, bupirimate, buthiobate, calcium polysulfide, captafol, captan, copper oxychloride, carpropamid, carbendazim, carboxin, CGA-279202 (test name), chinomethionat, chlobenthiazone, chlorfenazol, chloroneb, chlorothalonil, chlozolinate, cufraneb, cymoxanil, cyproconazol, cyprodinil, cypro
  • Step 2 Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]benzoic acid methyl ester
  • the reaction mixture was poured into 100 ml of ice water, extracted with ethyl acetate (50 ml ⁇ 2), the organic phase was washed with water, dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure.
  • the residual solid was subjected to purification with medium-pressure preparative liquid chromatography (Yamazen Corporation, medium pressure preparative system; YFLC-Wprep) that was eluted with ethyl acetate-hexane (1:1 to 1:3 gradient), and 4.05 g of the aimed product was obtained as white crystal.
  • Step 3 Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]benzoic acid
  • the reaction mixture was cooled with ice, and poured in 200 ml of water, and adjusted to pH 1-2 with concentrated hydrochloric acid, and then extracted with ethyl acetate (50 ml ⁇ 2), the organic phase was washed with water, dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 3.87 g of the aimed product as pale yellow crystal.
  • Step 4 Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(2,2,2-trifluoro ethyl)benzoic acid amide
  • reaction mixture was poured in 100 ml of water, and extracted with chloroform (20 ml ⁇ 3), the organic phase was washed with water, dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and passed through a glass filter packed with silica gel, and then the solvent was distilled off under reduced pressure. The residual solid was washed with hexane to obtain 1.05 g of the aimed product as white crystal.
  • Step 1 Production of 3-(4-bromomethyl-3-fluorophenyl)-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole
  • reaction mixture was left and cooled to room temperature, poured in 50 ml of water, extracted with chloroform (50 ml ⁇ 1). The organic phase was dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain crude aimed product as pale yellow oily substance. The resulting product was used as such without purification for the next step.
  • Step 2 Production of 3-(4-acetoxymethyl-3-fluorophenyl)-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole
  • Step 3 Production of 5-(3,5-dichlorophenyl)-3-(3-fluoro-4-hydroxymethylphenyl)-5-trifluoromethyl-4,5-dihydroisoxazole
  • the organic phase was dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure.
  • the residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (1:2) to obtain 0.95 g of the aimed product as pale yellow resinous substance.
  • Step 4 Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-fluoro benzoic acid
  • the organic phase was dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residual solid was washed with hexane to obtain 0.67 g of the aimed product as beige crystal.
  • Step 5 Production of N-benzyl-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-fluoro benzoic acid amide
  • Step 2 Production of 3-(4-bromo-3-nitrophenyl)-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole
  • the reaction mixture was poured in 50 ml of ice water, extracted with ethyl acetate (50 ml ⁇ 2), the organic phase was dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure.
  • the residual solid was subjected to purification with medium-pressure preparative liquid chromatography (Yamazen Corporation, medium pressure preparative system; YFLC-Wprep) that was eluted with ethyl acetate-hexane (1:2 to 1:4 gradient), and 1.10 g of the aimed product was obtained as yellow crystal.
  • Step 3 Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-nitrobenzoic acid ethyl ester
  • the reaction mixture was left and cooled to room temperature, and the solvent was distilled off under reduced pressure, and the residue was dissolved in 100 ml of ethyl acetate, washed with water, dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure.
  • the residual solid was subjected to purification with medium-pressure preparative liquid chromatography (Yamazen Corporation, medium pressure preparative system; YFLC-Wprep) that was eluted with ethyl acetate-hexane (1:2 to 1:4 gradient), and 0.66 g of the aimed product was obtained as pale yellow crystal.
  • Step 4 Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-nitro-N-(2-pyridylmethyl)benzoic acid amide
  • reaction mixture was poured in 15 ml of water, adjusted to pH 4 with concentrated hydrochloric acid, then extracted with ethyl acetate (20 ml ⁇ 2), the organic phase was washed with water, and then dehydrated with saturated sodium chloride aqueous solution and dried over over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure to obtain 0.40 g of crude 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-nitro benzoic acid as pale yellow oily substance.
  • the substance was dissolved in 10 ml of chloroform, and 0.24 g of 2-picolylamine, 0.01 g of 4-(N,N-dimethylamino)pyridine and 0.35 g of 1-[3-(diethylamino)propyl]-3-ethylcarbodiimide hydrochloride were added, and stirred at room temperature for 18 hours. After the completion of the reaction, the solvent was distilled off under reduced pressure.
  • Step 1 Production of 4-hydroxyiminomethyl-2-methoxyphenyl trifluoromethane sulfonate
  • Step 2 Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methoxyphenyl trifluoromethane sulfonate
  • the reaction mixture was poured in 100 ml of ice water, extracted with ethyl acetate (50 ml ⁇ 2), the organic phase was dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure.
  • the residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (1:7), and 1.4 g of the aimed product was obtained as colorless resinous substance.
  • Step 3 Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methoxy benzoic acid ethyl ester
  • reaction mixture was left and cooled to room temperature, and the reaction mixture was poured in 100 ml of ice water, extracted with ethyl acetate (40 ml ⁇ 2). The organic phases together were dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (1:5), and 1.20 g of the aimed product was obtained as white crystal.
  • Step 4 Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methoxy benzoic acid
  • Step 5 Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methoxy-N-(2,2,2-trifluoroethyl)benzoic acid amide
  • the mixture was continued to stir at the same temperature for further 2 hours. Thereafter, the reaction mixture was diluted with 60 ml of chloroform, washed with 50 ml of water, then dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (1:2) to obtain 0.25 g of the aimed product as colorless resinous substance.
  • Step 1 Production of 4-formyl-N-(2,2,2-trifluoroethyl)benzoic acid amide
  • Step 2 Production of 4-hydroxyiminomethyl-N-(2,2,2-trifluoroethyl)benzoic acid amide
  • Step 3 Production of 4-chlorohydroxyiminomethyl-(2,2,2-trifluoroethyl)benzoic acid amide
  • reaction mixture was poured in 200 ml of water, extracted with ethyl acetate (30 ml ⁇ 3), the organic phase was dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resudual solid was washed with hexane to obtain 4.15 g of the product as white crystal.
  • Step 4 Production of 4-[5-(4-fluoro-3-methylphenyl)-5-trifluoromethyl-4,5-dihydrooxazol-3-yl]-N-(2,2,2-trifluoroethyl)benzoic acid amide
  • reaction mixture was left and cooled to room temperature, then a solution of 0.25 g of 4-chlorohydroxyiminomethyl-N-(2,2,2-trifluoroethyl)benzoic acid amide in 4 ml of 1,2-dimethoxyethane was added, continued to stir at the same temperature for further 18 hours.
  • the reaction mixture was poured in 50 ml of water, extracted with ethyl acetate (10 ml ⁇ 3), the organic phase was dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resudual solid was purified with silica gel column chromatography that was eluated with chloroform to obtain 0.24 g of the product as white crystal.
  • Step 1 Production of 4-bromo-2-methyl-N-(2,2,2-trifluoroethyl)benzoic acid amide
  • Step 2 Production of 4-formyl-2-methyl-N-(2,2,2-trifluoroethyl)benzoic acid amide
  • Step 3 Production of 4-hydroxyiminomethyl-2-methyl-N-(2,2,2-trifluoroethyl)benzoic acid amide
  • Step 4 Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxasol-3-yl]-2-methyl-N-(2,2,2-trifluoroethyl)benzoic acid amide
  • reaction mixture was poured in 50 ml of ice water, extracted with ethyl acetate (50 ml ⁇ 1), the organic phase was dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure.
  • the residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (1:2), and 0.45 g of the aimed product was obtained as white crystal.
  • Step 1 Production of 4-bromo-2-methyl-N-(2-pyridylmethyl)benzoic acid amide
  • Step 2 Production of 4-formyl-2-methyl-N-(2-pyridylmethyl)benzoic acid amide
  • Step 3 Production of 4-hydroxyiminomethyl-2-methyl-N-(2-pyridylmethyl)benzoic acid amide
  • Step 4 Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-N-(2-pyridylmethyl)benzoic acid amide
  • the reaction mixture was poured in 50 ml of ice water, extracted with ethyl acetate (60 ml ⁇ 1), the organic phase was dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure.
  • the residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (3:1), and 0.30 g of the aimed product was obtained as white crystal.
  • Step 1 Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-iodo benzoic acid methyl ester
  • the organic phase was washed with water, dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure.
  • the residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (1:4), and 0.56 g of the aimed product was obtained as colorless oily substance.
  • Step 2 Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-trifluoromethyl benzoic acid methyl ester
  • the organic phase was washed with water, dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure.
  • the residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (1:4), and 0.45 g of the aimed product was obtained as pale yellow oily substance.
  • Step 3 Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-trifluoromethyl benzoic acid
  • the organic phase was washed with water, dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 0.34 g of the aimed product as pale yellow resinous substance.
  • the resulting product was used as such without purification for the next step.
  • Step 4 Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(2-pyridylmethyl)-2-trifluoromethyl benzoic acid amide
  • Step 1 Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-phenyl benzoic acid methyl ester
  • Step 2 Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-phenyl benzoic acid
  • the organic phase was washed with water, dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 0.70 g of the aimed product as brown glass substance.
  • the resulting product was used as such without purification for the next step.
  • Step 3 Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-phenyl-N-(2-pyridylmethyl)benzoic acid amide
  • the solvent was distilled off under reduced pressure, the residue was dissolved in 10 ml of chloroform, and under cooling with ice with stirring 0.3 ml of 2-picolylamine and then 0.3 ml of triethylamine were added, and continued to stir at room temperature for 20 minutes.
  • the reaction mixture was poured in 40 ml of water, extracted with ethyl acetate (50 ml ⁇ 1). The organic phase was washed with water, dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure.
  • the residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (2:1), and 0.2 g of the aimed product was obtained as white crystal.
  • Step 1 Production of 2-amino-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]benzoic acid ethyl ester
  • Step 2 Production of 2-amino-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]benzoic acid
  • Step 3 Production of 2-amino-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(2,2,2-trifluoroethyl)benzoic acid amide
  • the reaction mixture was subjected to purification with medium-pressure preparative liquid chromatography (Yamazen Corporation, medium pressure preparative system; YFLC-Wprep) that was eluted with ethyl acetate-hexane (1:4), and 0.14 g of the aimed product was obtained as pale yellow crystal.
  • medium-pressure preparative liquid chromatography Yamazen Corporation, medium pressure preparative system; YFLC-Wprep
  • the organic phase was washed with 30 ml of water, dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure.
  • the residue was purified with silica gel column chromatography that was eluated with chloroform, and 0.89 g of the aimed product was obtained as colorless oily substance.
  • the organic phase was washed with 30 ml of saturated sodium hydrogen carbonate, dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure.
  • the residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (1:2), and 0.17 g of the aimed product was obtained as colorless oily substance.
  • the organic phase was dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure.
  • the residue was purified with silica gel column chromatography that was eluated with chloroform, and 0.20 g of the aimed product was obtained as colorless oily substance.
  • the reaction mixture was subjected to purification with medium-pressure preparative liquid chromatography (Yamazen Corporation, medium pressure preparative system; YFLC-Wprep) that was eluted with ethyl acetate-hexane (1:8 to 1:1 gradient), and 0.045 g of the aimed product was obtained as pale yellow resinous substance.
  • medium-pressure preparative liquid chromatography Yamazen Corporation, medium pressure preparative system; YFLC-Wprep
  • reaction mixture was left and cooled to room temperature, diluted by adding 80 ml of ethyl acetate, washed with water (30 ml ⁇ 2), and dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure.
  • the residue was purified with silica gel column chromatography that was eluated with ethylacetate-hexane (1:1), and 102 mg of the aimed product was obtained as colorless resinous substance.
  • the reaction mixture was diluted with 80 ml of ethyl acetate, washed with water (50 ml ⁇ 2), dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure.
  • the residue was purified with high performance liquid chromatography that was eluated with acetonitrile-water (85:15) to obtain 0.25 g of the aimed product as colorless resinous substance.
  • reaction mixture was left and cooled to room temperature, and the reaction mixture was diluted with 60 ml of ethyl acetate, washed with water (50 ml ⁇ 1), then dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure.
  • the residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (3:1) to obtain 0.40 g of the aimed product as yellow resinous substance.
  • the organic phase was dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was dissolved in hexane, and high polar impurities were excluded by treating with silica gel to obtain 0.77 g of crude aimed product as colorless oily substance. The resulting product was used as such without purification for the next step.
  • Step 3 Production of 4-[5-(3-bromodifluoromethoxyphenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-N-(2,2,2-trifluoroethyl)benzoic acid amide
  • the organic phase was dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure.
  • the residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (1:1) to obtain 0.29 g of the aimed product as colorless glass substance.
  • reaction mixture was poured in 100 ml of saturated ammonium chloride aqueous solution, extracted with ethyl acetate (100 ml ⁇ 1).
  • the organic phase was dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure to obtain 4.6 g of crude aimed product as pale yellow oily substance.
  • the resulting product was used as such without purification for the next step.
  • reaction mixture was poured in 50 ml of ice water, extracted with ethyl acetate (50 ml ⁇ 1), the organic phase was dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with hexane to obtain 1.50 g of the aimed product as yellow oily substance.
  • Step 3 Production of 4-[5-chlorodifluoromethyl-5-(3,5-dichlorophenyl)-4,5-dihydroisoxazol-3-yl]-2-methyl-N-(2,2,2-trifluoroethyl)benzoic acid amide
  • Step 1 Production of 5-(3,5-dichlorophenyl)-3-(3-methyl-4-nitrophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole
  • Step 2 Production of 3-(4-amino-3-methylphenyl)-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole
  • Step 3 Production of 3-(4-bromo-3-methylphenyl)-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole
  • the diazo mixture was slowly added dropwise in a mixture of 1.0 ml of 47% hydrobromic acid and 0.28 g of copper (I) bromide at 60° C. with stirring, after the completion of the addition dropwise, continued to stir at 60° C. for further 2 hours.
  • 10 ml of water was added in the reaction mixture, extracted with ethyl acetate (20 ml ⁇ 2), the organic phases together were washed with water, then dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure.
  • the residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (1:10) to obtain 0.43 g of the aimed product as pale yellow crystal.
  • reaction mixture was left and cooled to room temperature, 200 ml of water was added and extracted with ethyl acetate (200 ml ⁇ 2), the organic phase was washed with water, dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluted with ethyl acetate-hexane (1:8) to obtain 10.8 g of the aimed product as colorless clear liquid.
  • Step 5 Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl benzoic acid
  • Step 6 Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-N-methoxycarbonyl-N-(2-pyridylmethyl)benzoic acid amide
  • reaction mixture was diluted with 60 ml of ethyl acetate, washed with 50 ml of water, then dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure.
  • the residue was purified with silica gel column chromatography that was eluted with ethyl acetate-hexane (1:2 to 1:1) to obtain 0.75 g of the aimed product as yellow resinous substance.
  • Step 2 Production of 3-(4-bromo-3-methylphenyl)-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole
  • Step 3 Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylbenzoyl chloride
  • Step 4 Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylbenzoic acid amide
  • the solvent was distilled off under reduced pressure, the residue was dissolved in 50 ml of ethyl acetate, washed with 50 ml of water, dehydrated and dried with saturated sodium chloride aqueous solution and anhydrous sodium sulfate in that order, and the solvent was distilled off under reduced pressure to obtain 2.9 g of the aimed product as orange crystal.
  • Step 1 Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-N-hydroxymethyl)benzoic acid amide
  • reaction mixture was diluted by adding 200 ml of ethyl acetate, washed with water (50 ml ⁇ 1) and then dehydrated and dried with saturated sodium chloride aqueous solution and anhydrous magnesium sulfate in that order, and filtered through silica gel, the solvent was distilled off under reduced pressure to obtain 7.00 g of crude aimed product as white crystal.
  • Step 2 Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-N-(2,2,2-trifluoroethoxymethyl)benzoic acid amide
  • the solvent was distilled off under reduced pressure, 50 ml of ethyl acetate and 50 ml of water were added in the residue, and the organic phase was collected, and the aqueous phase was further extracted with ethyl acetate (50 ml ⁇ 2).
  • the organic phases together were dehydrated and dried with saturated sodium chloride aqueous solution and anhydrous sodium sulfate in that order, and the solvent was distilled off under reduced pressure, the residual solid was washed with hexane to obtain 1.24 g of the aimed product as white crystal.
  • the compounds of the present invention can be produced according to the above-mentioned production methods and working examples.
  • the examples of the compounds produced similarly to Synthetic Examples 1 to 37 are shown in Tables 7 to 20 to which the present invention is not limited.
  • the indication “Et” means ethyl, hereinafter similarly thereto, “n-Pr” and “Pr-n” mean normal propyl, “i-Pr” and “Pr-i” mean isopropyl, “c-Pr” and “Pr-c” mean cyclopropyl, “n-Bu” and “Bu-n” mean normal butyl, “s-Bu” and “Bu-s” mean secondary butyl, “i-Bu” and “Bu-i” mean isobutyl, “t-Bu” and “Bu-t” mean tertiary butyl, “c-Bu” and “Bu-c” mean cyclobutyl, “n-Pen” and “Pen-n” means normal pentyl,
  • saturated heterocyclic rings of E-4-a to E-43a are the following structures, respectively,
  • T-4 to T-51 are the following structures, respectively.
  • the number showing the substitution position of substituents (X) m and (Y) n correspond to the position number indicated in the following structural formulae.
  • the indication “-” means no-substitution.
  • the indication of “Mw” shows the calculated value of molecular weight
  • the indication of “M + +H” shows the measured value of molecular ion peak
  • “*1”, “*2” or “*3” means “resinous”, “oily” or “decomposition”, respectively.
  • Substituent G in the above-mentioned formula is the structure of G-3, G-6, G-18 or G-20 mentioned below.
  • the indication of “(A)” in the table shows a condition in which tetramethylsilane is used as standard substance in chloroform-d solvent and measurement is carried out at 300 MHz (CDCl 3 , Me 4 Si, 300 MHz), hereinafter, the indication “(B)” shows the measurement condition of (CDCl 3 , Me 4 Si, 400 MHz), the indication of “(C)” shows the measurement condition of (CDCl 3 -DMSO-d 6 , Me 4 Si, 300 MHz), and the indication of “(D)” shows the measurement condition of (CDCl 3 -DMSO-d 6 , Me 4 Si, 400 MHz).
  • 4-004 (A) ⁇ 8.55-8.65 (m, 1H), 7.35-7.8 (m, 9H), 7.1-7.3 (m, 1H), 4.6-5.15 (m, 4H), 3.3-4.2 (m, 4H), 1.1-1.35 (m, 3H).
  • 5-030 A) ⁇ 7.2-7.45 (m, 6H), 6.49 (bs, 1H), 4.0-4.15 (m, 2H), 3.46 (s, 2H), 2.40 (s, 3H), 1.79 (s, 3H).
  • 5-336 A) ⁇ 8.45-8.6 (m, 1H), 8.23 and 8.29 (s, 1H), 7.15-7.9 (m, 10H), 4.65-4.75 (m, 2H), 4.0-4.2 (m, 1H), 3.6-3.8 (m, 1H), 3.25 and 3.34 (s, 3H).
  • 5-337 A) ⁇ 8.45-8.6 (m, 1H), 7.15-8.05 (m, 10H), 4.65-4.75 (m, 2H), 4.0-4.2 (m, 1H), 3.65-3.8 (m, 1H), 3.33 and 3.22 (s, 3H), 2.19 and 1.87 (s, 3H).

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Abstract

A substituted alkenylbenzene compound of formula (4):
Figure US20150105398A1-20150416-C00001
wherein X1 is selected from the group consisting of a halogen atom, —SF5, C1-C6haloalkyl, hydroxy C1-C6haloalkyl, C1-C6alkoxy C1-C6haloalkyl, C3-C8halocycloalkyl, C1-C6 haloalkoxy C1-C3haloalkoxy C1-C3haloalkoxy, C1-C6haloalkylthio, C1-C6haloalkylsulfinyl and C1-C6haloalkylsulfonyl; X3 is selected from the group consisting of a hydrogen atom, halogen atom, cyano, nitro, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy and C1-C6 alkylthio; X4 is selected from the group consisting of a hydrogen atom, halogen atom, cyano, C1-C4alkyl, C1-C4alkoxy and C1-C4haloalkoxy; R3 is —C(R3a)(R3b)R3c, where R3a and R3b independently of each other are a halogen atom, or R3a and R3b together form 3- to 6-membered ring together with the carbon atom bonding them by forming a C2-C5haloalkylene chain, and R3c is selected from the group consisting of a hydrogen atom, halogen atom, C1-C5alkyl, C1-C5haloalkyl, C1-C4haloalkoxy and C1-C4haloalkylthio, with a proviso that in case here X1 is a fluorine atom, chlorine atom or trifluoromethyl, and both X2 and X3 are a hydrogen atom, in case where both X1 and X2 are fluorine atom and X3 is a hydrogen atom, and in case where both X1 and X2 are trifluoromethyl and X3 is a hydrogen atom, R3c is a hydrogen atom, chlorine atom, bromine atom, iodine atom, C1-C5alkyl, C1-C5haloalkyl, C1-C4haloalkoxy or C1-C4haloalkylthio.

Description

  • This is a Divisional application of application Ser. No. 13/166,294, filed Jun. 22, 2011, which is a Divisional application of application Ser. No. 12/509,859, filed on Jul. 27, 2009, which is a Divisional application of application Ser. No. 11/514,921, filed Sep. 5, 2006, which in turn is a Continuation-in-part of International Application No. PCT/JP05/04268, filed Mar. 4, 2005, which claims priority to Japanese Patent Applications Nos. 2004-200119, filed Jul. 7, 2004, and 2004-061749, filed Mar. 5, 2004. The disclosures of the prior applications are hereby incorporated by reference herein in their entirety.
    • TECHNICAL FIELD
  • The present invention relates to a novel isoxazoline-substituted benzamide compound and the salt thereof, and a pesticide characterized by containing the compound as an active ingredient. The pesticide in the present invention means a pest controlling agent applied for harmful arthropods in agricultural and horticultural field or livestock farming and hygienic field (endo-parasiticides and ecto-parasiticides for mammals or birds as domestic animals or pets, or hygienic pest- or unpleasant pest-controlling agents for domestic or business use). In addition, agricultural chemicals in the present invention mean insecticides, acaricides (miticides), nematicides, herbicides and fungicides, and the like.
    • BACKGROUND ART
  • Conventionally, as to isoxazoline-substituted benzoic acid amide compounds, the followings are known: a report of synthesis by use of solid phase synthesis of 4-(5-methyl-5-substituted pyrrolyl-4,5-dihydroisoxazole-3-yl)benzoic acid amide derivatives (see, Non-patent Document 1); 4-(5-pyridyl-4,5-dihydroisoxazole-3-yl)benzoic acid amide derivatives have matrix metalloprotease and TNF-inhibition activity, or the like, and can be used as an anti-inflammatory agent or a chondro-protective agent (see, Patent Document 1); 4-(5-substituted carbamoylmethyl-4,5-dihydroisoxazole-3-yl)benzoic acid amide derivatives, 3-(5-substituted carbamoylmethyl-5-substituted alkyl-4,5-dihydroisoxazole-3-yl)benzoic acid amide derivatives and 4-(5-substituted carbamoylmethyl-4,5-dihydroisoxazole-3-yl)benzamidine derivatives have platelet glycoprotein IIb/IIIa fibrinogen receptor complex competitive activity or factor Xa inhibition activity or the like, and can be used as a thrombolysis agent or a therapeutic agent of thronbo-embolic disorder (see, for example Patent Documents 2-5), etc. In addition, it is known that other specific substituted isoxazoline compound can be used as a production intermediate of HIV protease inhibitors, or production intermediate of insecticides (see, for example Patent Documents 6 and 7). However, there is no disclosure on 4-(5-substituted-5-substituted aryl-4,5-dihydroisoxazole-3-yl)benzoic acid amide compounds according to the present invention, and further the usefulness thereof as a pesticide is not known at all.
  • On the other hand, as to 3-(4-substituted phenyl)-4,5-dihydroisoxazole derivatives, 5-substituted alkyl-3,5-bis substituted phenyl-4,5-dihydroisoxazole derivatives (see, Patent Document 7), 3-alkoxyphenyl-5-substituted-5-phenyl-4,5-dihydroisoxazole derivatives (see, Patent Document 8), 3-alkoxyphenyl-5-substituted alkyl-5-substituted carbamoyl-4,5-dihydroisoxazole derivatives (see, Patent Document 9), 3-(4-halophenyl)-5-substituted-5-substituted phenyl-4,5-dihydroisoxazole derivatives (see, Patent Documents 10 and Non-patent Document 2), and 3-(4-nitrophenyl)-5-substituted-5-substituted phenyl-4,5-dihydroisoxazole derivatives (see, patent Document 11 and Non-patent Document 3), etc. are known. However, 5-substituted alkyl-3,5-bis substituted phenyl-4,5-dihydroisoxazole derivatives that can be used as a production intermediate of the pesticides according to the present invention are not described in any documents and thus novel compounds.
  • Further, as to 4-hydroxyiminomethyl benzoic acid amide derivatives, 4-hydroxyiminomethyl-N,N-dimethyl benzoic acid amide (see, Non-patent Document 4), 4-hydroxyiminomethyl benzoyl piperidine derivatives (see, Patent Documents 12 and 13), 4-hydroxyiminomethyl-N-bicycloalkyl benzoic acid amide derivatives (see, Patent Document 14), and 6-(hydroxyiminomethyl)pyridine-2-carboxamide derivatives (see, Non-patent Document 5), etc. are known. However, 4-hydroxyiminomethyl benzoic acid amide derivatives that can be used as a production intermediate of the pesticides according to the present invention are not described in any documents and thus novel compounds.
  • In addition, as to haloalkenylbenzene derivatives, substituted 3,3,3-trifluoro-2-propenylbenzene derivatives (see, Non-patent Documents 6-8), etc. are known. However, specific substituted haloalkenylbenzene derivatives that can be used as a production intermediate of the pesticides according to the present invention are not described in any documents and thus novel compounds.
    • Patent Document 1: WO 01/070673 Pamphlet
    • Patent Document 2: WO 96/038426 Pamphlet
    • Patent Document 3: WO 97/023212 Pamphlet
    • Patent Document 4: WO 95/014683 Pamphlet
    • Patent Document 5: WO 97/048395 Pamphlet
    • Patent Document 6: WO 99/014210 Pamphlet
    • Patent Document 7: WO 04/018410 Pamphlet
    • Patent Document 8: WO 95/024398 Pamphlet
    • Patent Document 9: WO 98/057937 Pamphlet
    • Patent Document 10: EP 0455052 A1 (1991)
    • Patent Document 11: WO 2004/018410 Pamphlet
    • Patent Document 12: WO 95/019773 Pamphlet
    • Patent Document 13: WO 00/066558 Pamphlet
    • Patent Document 14: WO 97/000853 Pamphlet
    • Non-patent Document 1: J. Comb. Chem., vol. 6, p. 142 (2004)
    • Non-patent Document 2: Synth. Commun., vol. 33, p. 4163 (2003)
    • Non-patent Document 3: Australian J. Chem., vol. 32, p. 1487 (1979)
    • Non-patent Document 4: J. Chem. Soc. Perkin Trans, 1, p. 643 (1979)
    • Non-patent Document 5: J. Org. Chem., vol. 35, p. 841 (1970)
    • Non-patent Document 6: J. Org. Chem., vol. 24, p. 238 (1959)
    • Non-patent Document 7: J. Am. Chem. Soc., vol. 101, p. 357 (1979)
    • Non-patent Document 8: Bull. Chem. Soc. Jpn., vol. 69, p. 3273 (1996)
    DISCLOSURE OF INVENTION Problems to be Solved by the Invention
  • Recently, pests acquire resistance by the use of pesticides such as insecticides or fungicides over long term, and thus control by the insecticides or fungicides that have been conventionally used becomes difficult. In addition, a part of known pesticides has a high toxicity, or some of them start to disturb native ecosystems due to long-term persistency. Under the circumstances, it is expected all the time to develop a novel pesticide having a low toxicity and a low persistency.
    • Means for Solving the Problems
  • The inventors have eagerly investigated in order to solve the above-mentioned problems, and as a result of it, they found that novel isoxazoline-substituted benzamide compounds of formula (I) are extremely useful compounds having excellent pest controlling activity, particularly insecticidal activity and acaricidal activity, and having little adverse affect on non-targeted beings such as mammals, fishes and useful insects, etc. Thus, the present invention has been accomplished.
  • That is, the present invention relates to the following aspects (1) to (15):
  • (1) An isoxazoline-substituted benzamide compound of formula (1) or a salt thereof:
  • Figure US20150105398A1-20150416-C00002
  • wherein A1, A2 and A3 independently of one another are carbon atom or nitrogen atom,
    G is benzene ring, nitrogen-containing 6-membered aromatic heterocyclic ring, furan ring, thiophene ring, or 5-membered aromatic heterocyclic ring containing two or more hetero atoms selected from oxygen atom, sulfur atom and nitrogen atom,
    W is oxygen atom or sulfur atom,
    X is halogen atom, cyano, nitro, azido, —SCN, —SF5, C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R4, C3-C8cycloalkyl, C3-C8cycloalkyl arbitrarily substituted with R4, C2-C6alkenyl, C2-C6alkenyl arbitrarily substituted with R4, C3-C8cycloalkenyl, C3-C8halocycloalkenyl, C2-C6alkynyl, C2-C6alkynyl arbitrarily substituted with R4, —OH, —OR5, —OSO2R5, —SH, —S(O)rR5, —N═CHOR8, —N═C(R9)OR8, —CHO, —C(O)R9, —C(O)OR9, —C(O)SR9, —C(O)NHR10, —C(O)N(R10)R9, —C(S)OR9, —C(S)SR9, —C(S)NHR10, —C(S)N(R10)R9, —CH═NOR11, —C(R9)═NOR11, —S(O)2OR9, —S(O)2NHR10, —S(O)2N(R10)R9, —Si(R13)(R14)R12, phenyl, phenyl substituted with (Z)p1, D-1 to D-65 or E-1 to E-49, when m is 2, 3, 4 or 5, each X may be identical with or different from each other,
    further, when two Xs are adjacent, the adjacent two Xs may form 5-membered or 6-membered ring together with carbon atoms to which the two Xs are bonded by forming —CH2CH2CH2—, —CH2CH2O—, —CH2OCH2—, —OCH2O—, —CH2CH2S—, —CH2SCH2—, —CH2CH2N(R15)—, —CH2N(R15)CH2—, —CH2CH2CH2CH2—, —CH2CH2CH2O—, —CH2CH2OCH2—, —CH2OCH2O—, —OCH2CH2O—, —OCH2CH2S—, —CH2CH═CH—, —OCH═CH—, —SCH═CH—, —N(R15)CH═CH—, —OCH═N—, —SCH═N—, —N(R15)CH═N—, —N(R15)N═CH—, —CH═CHCH═CH—, —OCH2CH═CH—, —N═CHCH═CH—, —N═CHCH═N— or —N═CHN═CH—, in this case, hydrogen atoms bonded to each carbon atom forming the ring may be arbitrarily substituted with Z, further when the hydrogen atoms are substituted with two or more Zs at the same time, each Z may be identical with or different from each other,
    Y is halogen atom, cyano, nitro, azido, —SCN, —SF5, C1-C6alkyl, C1-C8alkyl arbitrarily substituted with R4, C3-C8cycloalkyl, C3-C8cycloalkyl arbitrarily substituted with R4, C2-C6alkynyl, C2-C6alkynyl arbitrarily substituted with R4, —OH, —OR5, —OSO2R5, —SH, —S(O)rR5, —NHR7, —N(R7)R6, —N═CHOR8, —N═C(R9)OR8, —C(O)NHR10, —C(O)N(R10)R9, —C(S)NHR10, —C(S)N(R10)R9, —Si(R13)(R14)R12, phenyl, phenyl substituted with (Z)p1, D-1 to D-65 or E-1 to E-49, when n is 2, 3 or 4, each Y may be identical with or different from each other,
    further, when two Ys are adjacent, the adjacent two Ys may form 5-membered or 6-membered ring together with carbon atoms to which the two Ys are bonded by forming —CH2CH2CH2—, —CH2CH2O—, —CH2OCH2—, —OCH2O—, —CH2CH2S—, —CH2SCH2—, —SCH2S—, —CH2CH2CH2CH2—, —CH2CH2CH2O—, —CH2CH2OCH2—, —CH2OCH2O—, —OCH2CH2O—, —OCH2CH2S—, —SCH2CH2S—, —OCH═N— or —SCH═N—, in this case, hydrogen atoms bonded to each carbon atom forming the ring may be arbitrarily substituted with Z, further when the hydrogen atoms are substituted with two or more Zs at the same time, each Z may be identical with or different from each other, R1 and R2 independently of each other are hydrogen atom, cyano, C1-C12alkyl, C1-C12alkyl arbitrarily substituted with R16, C3-C12cycloalkyl, C3-C12cycloalkyl arbitrarily substituted with R16, C2-C12alkenyl, C2-C12alkenyl arbitrarily substituted with R16, C3-C12cycloalkenyl, C3-C12halocycloalkenyl, C3-C12alkynyl, C3-C12alkynyl arbitrarily substituted with R16, —SW, —S(O)2R9, —SN(R18)R17, —S(O)2N(R10)R9, —OR19, —N(R20)R19, —N═CHR19b, —N═C(R19b)R19a, —CHO, —C(O)R9, —C(O)OR9, —C(O)SR9, —C(O)N(R10)R9, —C(S)OR9, —C(S)SR9, —C(S)N(R10)R9, —C(═NR11)OR9, —C(═NR11)SR9, —C(═NR11)N(R10)R9, phenyl, phenyl substituted with (Z)p1, D-1 to D-63, D-65, E-3 to E-9, E17, E-23 to E-31, E-33, E-34 or E-45, or R1 and R2 together form ═C(R2a)R1a, or R1 and R2 together may form 3- to 8-membered ring together with the nitrogen atom bonding them by forming C2-C7 alkylene chain, in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and may be arbitrarily substituted with halogen atom, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy (C1-C6)alkyl, C1-C6alkoxy, formyl, C1-C6alkylcarbonyl, C1-C6haloalkylcarbonyl, C1-C6alkoxycarbonyl, C1-C6haloalkoxycarbonyl, C1-C6alkylaminocarbonyl, C1-C6haloalkylaminocarbonyl, phenyl, phenyl substituted with (Z)p1, D-47, D-50, D-51, D-53 or 54,
    or in case where substituent Y is present at the adjacent position, R2 together with Y may form 5- or 6-membered ring together with the atom bonding them by forming —CH2—, —CH2CH2—, —CH2O—, —CH2S—, —CH2N(R6)—, —CH═CH— or —CH═N—, in this case, hydrogen atoms bonded to each carbon atom forming the ring may be arbitrarily substituted with halogen atom, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkylidene, C1-C6haloalkylidene, oxo or thioxo,
    R1a and R2a together may form 5- or 6-membered ring together with the carbon atom bonding them by forming C4-C6 alkylene chain or C4-C6 alkenylene chain, in this case, the alkylene chain and the alkenylene chain may contain one to three oxygen atoms, sulfur atoms or nitrogen atoms, and may be arbitrarily substituted with halogen atom, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, C1-C6alkylthio or C1-C6haloalkylthio,
    R3 is halogen atom, cyano, C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R4, C3-C8cycloalkyl, C3-C8cycloalkyl arbitrarily substituted with R4, C3-C6alkenyl, C2-C6alkenyl arbitrarily substituted with R4, C3-C6alkynyl, C2-C6alkynyl arbitrarily substituted with R4, —OR5, —S(O)rR5, —N(R10)R9, —CHO, —C(O)R9, —C(O)OR9, —C(O)SR9, —C(O)NHR10, —C(O)N(R10)R9, —C(S)OR9, —C(S)SR9, —C(S)NHR10, —C(S)N(R10)R9, —CH═NOR11, —C(R9)═NOR11, —Si(R13)(R14)R12, —P(O)(OR21)2, phenyl, phenyl substituted with (Z)p1, D-1 to D-65 or E-1 to E-49,
    D-1 to D-65 are aromatic heterocyclic rings of the following formulae, respectively
  • Figure US20150105398A1-20150416-C00003
    Figure US20150105398A1-20150416-C00004
    Figure US20150105398A1-20150416-C00005
    Figure US20150105398A1-20150416-C00006
    Figure US20150105398A1-20150416-C00007
    Figure US20150105398A1-20150416-C00008
  • Z is halogen atom, cyano, nitro, C1-C6alkyl, C1-C6haloalkyl, C1-C4alkoxy C1-C4alkyl, C1-C4haloalkoxy C1-C4alkyl, C1-C4alkylthio C1-C4alkyl, C1-C4haloalkylthio C1-C4alkyl, C1-C4alkylsulfinyl C1-C4alkyl, C1-C4haloalkylsulfinyl C1-C4alkyl, C1-C4alkylsulfonyl C1-C4alkyl, C1-C4haloalkylsulfonyl C1-C4alkyl, C3-C6cycloalkyl, C3-C6halocycloalkyl, —OH, C1-C6alkoxy, C1-C6haloalkoxy, C1-C6alkylsulfonyloxy, C1-C6haloalkylsulfonyloxy, C1-C6alkylthio, C1-C6haloalkylthio, C1-C6alkylsulfinyl, C1-C6haloalkylsulfinyl, C1-C6alkylsulfonyl, C1-C6haloalkylsulfonyl, —NH2, C1-C6alkylamino, di(C1-C6alkyl)amino, C1-C6alkoxycarbonyl, C1-C6haloalkoxycarbonyl, —C(O)NH2, C1-C6alkylaminocarbonyl, C1-C6haloalkylaminocarbonyl, di(C1-C6alkyl)aminocarbonyl, —C(S)NH2, —S(O)2NH2, C1-C6alkylaminosulfonyl, di(C1-C6alkyl)aminosulfonyl, phenyl or phenyl arbitrarily substituted with halogen atom, when p1, p2, p3 or p4 is an integer of 2 or more,
    each Z may be identical with or different from each other,
    further, when two Zs are adjacent, the adjacent two Zs may form 5-membered or 6-membered ring together with carbon atoms to which the two Zs are bonded by forming —CH2CH2CH2—, —CH2CH2O—, —CH2OCH2—, —OCH2O—, —CH2CH2S—, —CH2SCH2—, —CH2CH2CH2CH2—, —CH2CH2CH2O—, —CH2CH2OCH2—, —CH2OCH2O—, —OCH2CH2O—, —CH2CH2CH2S—, —OCH2CH2S— or —CH═CH—CH═CH—, in this case, hydrogen atoms bonded to each carbon atom forming the ring may be arbitrarily substituted with halogen atom, cyano, nitro, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy or C1-C4alkylthio,
    E-1 to E-49 are saturated heterocyclic rings of the following formulae, respectively
  • Figure US20150105398A1-20150416-C00009
    Figure US20150105398A1-20150416-C00010
    Figure US20150105398A1-20150416-C00011
    Figure US20150105398A1-20150416-C00012
    Figure US20150105398A1-20150416-C00013
  • R4 is halogen atom, cyano, C3-C8cycloalkyl, C3-C8halocycloalkyl, —OH, —OR5, —SH, —S(O)rR5, —N(R10)R9, —N(R10)CHO, —N(R10)C(O)R9, —N(R10)C(O)OR9, —N(R10)C(O)SR9, —N(R10)C(S)OR9, —N(R10)C(S)SR9, —N(R10)S(O)2R9, —C(O)OR9, —C(O)N(R10)R9, —Si(R13)(R14)R12, phenyl, phenyl substituted with (Z)p1, D-1 to D-65 or E-1 to E-49,
    R5 is C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R24, C3-C8cycloalkyl, C3-C8cycloalkyl arbitrarily substituted with R24, C2-C6alkenyl, C2-C6alkenyl arbitrarily substituted with R24, C3-C8cycloalkenyl, C3-C8halocycloalkenyl, C3-C6alkynyl, C3-C6alkynyl arbitrarily substituted with R24, C1-C6alkylcarbonyl, C1-C6alkoxycarbonyl, phenyl, phenyl substituted with (Z)p1, D-1 to D-4, D-6 to D-13, D-15 to D-23, D-25 to D-37, D-39, D-40, D-42, D-45 to D-60, D-62, D-63, D-65, E-3 to E-9, E-23 to E-31, E-34 or E-45,
    R6 is C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R24, C3-C6cycloalkyl, C3-C8halocycloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl, —OH, C1-C6alkylcarbonyloxy, C1-C6alkylthio, C1-C6haloalkylthio, phenylthio, phenylthio substituted with (Z)p1, —SN(R18)R17, —S(O)2R9, —S(O)2N(R10)R9, —CHO, —C(O)R9, —C(O)OR9, —C(O)SR9, —C(O)NHR10, —C(O)N(R10)R9, —C(S)OR9, —C(S)SR9, —C(S)NHR10, —C(S)N(R10)R9, —C(O)C(O)R9, —C(O)C(O)OR9, —P(O)(OR21)2 or —P(S)(OR21)2,
    R7 is hydrogen atom, C1-C6alkyl, C1-C6haloalkyl, C3-C8cycloalkyl C1-C6alkyl, C1-C4alkoxy C1-C4alkyl, C1-C4 alkylthio C1-C4alkyl, C3-C8cycloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl, —CHO, C1-C6alkylcarbonyl, C1-C6haloalkylcarbonyl or C1-C6alkoxycarbonyl, or R7 together with R6 may form 3- to 7-membered ring with the bonding nitrogen atom by forming C2-C6alkylene chain, in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and may be arbitrarily substituted with halogen atom, C1-C6alkyl, C1-C6haloalkyl, oxo or thioxo,
    R8 is C1-C6alkyl, C1-C6haloalkyl, C3-C6alkenyl, phenyl or phenyl substituted with (Z)p1,
    R9 is C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R24, C3-C8cycloalkyl, C3-C8halocycloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, phenyl, phenyl substituted with (Z)p1, D-1 to D-65 or E-1 to E-49,
    R10 is hydrogen atom, C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl C1-C4alkyl, C1-C6alkoxy C1-C4alkyl, C1-C6alkylthio C1-C4alkyl, cyano C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl, R10 together with R9 may form 3- to 7-membered ring with the atom bonding them by forming C2-C6alkylene chain, in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and may be arbitrarily substituted with halogen atom, C1-C6alkyl or C1-C6haloalkoxy, formyl, C1-C6alkylcarbonyl or C1-C6alkoxycarbonyl,
    R11 is hydrogen atom, C1-C6alkyl, C1-C6haloalkyl, phenyl C1-C4alkyl, phenyl C1-C4alkyl substituted with (Z)p1, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl, phenyl or phenyl that may be substituted with (Z)p1, R11 together with R9 may form 5- to 7-membered ring with the atom bonding them by forming C2-C4alkylene chain, in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and may be arbitrarily substituted with halogen atom, C1-C6alkyl or C1-C6haloalkyl,
    R12 is C1-C6alkyl, C1-C6haloalkyl, phenyl or phenyl substituted with (Z)p1,
    R13 and R14 independently of each other are C1-C6alkyl or C1-C6haloalkyl,
    R15 is hydrogen atom, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxycarbonyl C1-C4alkyl, C1-C6haloalkoxycarbonyl C1-C4alkyl, phenyl C1-C4alkyl, phenyl C1-C4alkyl substituted with (Z)p1, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl, C1-C6alkoxy, C1-C6alkoxycarbonyl, C1-C6haloalkoxycarbonyl, phenyl or phenyl substituted with (Z)p1,
    further, in case where Z is present in an adjacent position of R15, the adjacent R15 and Z may form 6-membered ring together with the atom bonding them by forming —CH2CH2CH2CH2—, —CH═CH—CH═CH—, —N═CH—CH═CH—, —CH═N—CH═CH—, —CH═CH—N═CH— or —CH═CH—CH═N—, in this case, hydrogen atoms bonded to each carbon atom forming the ring may be arbitrarily substituted with halogen atom, C1-C4alkyl or C1-C4haloalkyl,
    R16 is halogen atom, cyano, nitro, C3-C8cycloalkyl, C3-C8halocycloalkyl, hydroxy C3-C6cycloalkyl, C1-C4alkoxy C3-C6cycloalkyl, C5-C6cycloalkenyl, —OR25, —N(R26)R25, —SH, —S(O)rR27, —SO2OH, —SO2NHR29, —SO2N(R29)R28, —CHO, —C(O)R28, —C(O)OH, —C(O)OR28, —C(O)SR28, —C(O)NHR29, —C(O)N(R29)R28, —C(O)N(R29)OR28, —C(O)N(R29)N(R28a) R28, —C(S)OR28, —C(S)SR28, —C(S)NHR29, —C(S)N(R29)R28, —C(O)C(O)OR28, —C(R31)═NOH, —C(R31)═NOR30, —C(═NR31)OR30, —C(═NR31)SR30, —C(═NR31)N(R29)R30, —C(═NOR31)NHR29, —C(═NOR31)N(R29)R30, —Si(R13)(R14)R12, —P(O)(OR21)2, —P(S)(OR21)2, —P(phenyl)2, —P(O)(phenyl)2, phenyl, phenyl substituted with (Z)p1, naphthyl, D-1 to D-65, E-1 to E-49 or M-1 to M-22,
    M-1 to M-22 are partially saturated heterocyclic rings of the following formulae, respectively
  • Figure US20150105398A1-20150416-C00014
    Figure US20150105398A1-20150416-C00015
    Figure US20150105398A1-20150416-C00016
  • R17 is C1-C12alkyl, C1-C12haloalkyl, C1-C12alkoxy C1-C12alkyl, cyano C1-C12alkyl, C1-C12alkoxycarbonyl C1-C12alkyl, phenyl C1-C4alkyl, phenyl C1-C4alkyl substituted with (Z)p1, C3-C12alkenyl, C3-C12haloalkenyl, C3-C12alkynyl, C3-C12haloalkynyl, C1-C12alkylcarbonyl, C1-C12alkoxycarbonyl, —C(O)ON═C(CH3)SCH3, —C(O)ON═C(SCH3)C(O)N(CH3)2, phenyl or phenyl substituted with (Z)p1,
    R18 is C1-C12alkyl, C1-C12haloalkyl, C1-C12alkoxy C1-C12alkyl, cyano C1-C12alkyl, C1-C12alkoxycarbonyl C1-C12alkyl, phenyl C1-C4alkyl, phenyl C1-C4alkyl substituted with (Z)p1, C3-C12alkenyl, C3-C12haloalkenyl, C3-C12alkynyl, C3-C12haloalkynyl, phenyl or phenyl substituted with (Z)p1, or R18 together with R17 may form 5- to 8-membered ring with the nitrogen atom bonding them by forming C4-C7alkylene chain, in this case, the alkylene chain may contain one oxygen atom or sulfur atom, and may be arbitrarily substituted with C1-C4alkyl or C1-C4alkoxy,
    R19 is hydrogen atom, C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R16, C3-C8cycloalkyl, C3-C8halocycloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl, —CHO, —C(O)R28, —C(O)OR28, —C(O)SR28, —C(O)NHR29, —C(O)N(R29)R28, —C(S)OR28, —C(S)SR28, —C(S)NHR29, —C(S)N(R29)R28, —S(O)2R28, —S(O)2NHR29, —S(O)2N(R29)R28, —P(O)(OR21)2, —P(S)(OR21)2, phenyl, phenyl substituted with (Z)p1, D-1 to D-13, D-15 to D-25, D-30 to D-37, D-39, D-40, D-42, D-45 to D-60, E-5, E-7, E-9, E-24, E-25, E-27, E-28, E-30 or E-31,
    R19a is hydrogen atom, C1-C6alkyl, C1-C6haloalkyl, C1-C4alkoxy C1-C4alkyl, C1-C4alkylthio C1-C4alkyl, C1-C4alkylsulfonyl C1-C4alkyl, C1-C4alkoxycarbonyl C1-C4alkyl, phenyl C1-C4alkyl, phenyl C1-C4alkyl substituted with (Z)p1, C3-C6cycloalkyl, phenyl C2-C4alkenyl, di(C1-C6alkyl)amino, phenyl, phenyl substituted with (Z)p1, D-1 to D-65 or E-1 to E-49,
    R19b is hydrogen atom, C1-C6alkyl, C1-C6alkoxy, C1-C6alkylthio or di(C1-C6alkyl)amino, or R19a together with R19b may form 4- to 6-membered ring with the carbon atom bonding them by forming C3-C5alkylene chain, in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and may be arbitrarily substituted with halogen atom, C1-C6alkyl, C1-C6haloalkyl, formyl, C1-C6alkylcarbonyl or C1-C6alkoxycarbonyl,
    R20 is hydrogen atom, C1-C6alkyl, C1-C6haloalkyl, C1-C4alkoxy C1-C4alkyl, C1-C4haloalkoxy C1-C4alkyl, C1-C4alkylthio C1-C4alkyl, C1-C4haloalkylthio C1-C4alkyl, C1-C4alkylsulfonyl C1-C4alkyl, C1-C4haloalkylsulfonyl C1-C4alkyl, cyano C1-C6alkyl, C1-C4alkoxycarbonyl C1-C4alkyl, phenyl C1-C4alkyl, C2-C6alkenyl, C2-C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl, —CHO, —C(O)R9, —C(O)OR9, —C(O)SR9, —C(S)OR9, —C(S)SR9, C1-C6alkylsulfonyl or C1-C6haloalkylsulfonyl, or R20 together with R19 may form 5- to 6-membered ring with the nitrogen atom bonding them by forming C4-C5alkylene chain, in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and may be arbitrarily substituted with C1-C6alkyl, C1-C6alkoxy C1-C6alkyl, —CHO, C1-C6alkylcarbonyl or C1-C6alkoxycarbonyl,
    R21 is C1-C6alkyl or C1-C6haloalkyl,
    R22 is halogen atom, cyano, C1-C6alkyl, C1-C6haloalkyl, hydroxy C1-C6alkyl, C1-C4alkoxy C1-C4alkyl, C1-C4alkoxycarbonyl C1-C4alkyl, C1-C6alkoxy, C1-C6alkylthio, C1-C6alkylamino, di(C1-C4alkyl)amino, C1-C6alkoxycarbonyl, phenyl or phenyl substituted with (Z)p1, when q1, q2, q3 or q4 is an integer of 2 or more, each R22 may be identical with or different from each other, further in case where two R22s are present on the same carbon atom, the two R22s together may form oxo, thioxo, imino, C1-C6alkylimino, C1-C6alkoxyimino or C1-C6alkylidene,
    R23 is hydrogen atom, C1-C6alkyl, C1-C6alkyl substituted with R32, C3-C6cycloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, —OH, benzyloxy, —CHO, —C(O)R33, —C(O)OR33, —C(O)SR33, —C(O)NHR34, —C(O)N(R34)R33, —C(S)NHR34, —C(S)N(R34)R33, —S(O)2R33, —P(O)(OR21)2, —P(S)(OR21)2, phenyl, phenyl substituted with (Z)p1 or D-5,
    R24 is halogen atom, cyano, C3-C8cycloalkyl, C3-C8halocycloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, C1-C6alkylthio, C1-C6haloalkylthio, C1-C6alkylsulfonyl, C1-C6haloalkylsulfonyl, C1-C6alkylamino, di(C1-C6alkyl)amino, —CHO, C1-C6alkylcarbonyl, C1-C6haloalkylcarbonyl, C1-C6alkoxycarbonyl, C1-C6haloalkoxycarbonyl, C1-C6alkylaminocarbonyl, di(C1-C6alkyl)aminocarbonyl, phenyl, phenyl substituted with (Z)p1, D-1 to D-65 or E-1 to E-49,
    R25 is hydrogen atom, C1-C8alkyl, C1-C8alkyl arbitrarily substituted with R32, C3-C8cycloalkyl, C3-C8cycloalkyl arbitrarily substituted with R32, C3-C8alkenyl, C3-C8alkenyl arbitrarily substituted with R32, C3-C8alkynyl, C3-C8alkynyl arbitrarily substituted with R32, —CHO, —C(O)R33, —C(O)OR33, —C(O)SR33, —C(O)NHR34, —C(O)N(R34)R33, —C(O)C(O)R33, —C(O)C(O)OR33, —C(S)R33, —C(S)OR33, —C(S)SR33, —C(S)NHR34, —C(S)N(R34)R33, —S(O)2R33, —S(O)2N(R34)R33, —Si(R13)(R14)R12, —P(O)(OR21)2, —P(S)(OR21)2, phenyl, phenyl substituted with (Z)p1, D-1 to D-4, D-6 to D-13, D-15 to D-23, D-25 to D-37, D-39, D-40, D-42, D-45 to D-60, D-62, D-63, D-65, E-3 to E-9, E-23 to E-31, E-34 or E-45,
    R26 is hydrogen atom, C1-C6alkyl, C1-C6haloalkyl, C1-C4alkoxy C1-C4alkyl, C1-C4alkylthio C1-C4alkyl, C3-C6cycloalkyl, C3-C6alkenyl, C3-C6alkynyl, C1-C6alkoxy, phenyl or phenyl substituted with (Z)p1, or R26 together with R25 may form 3- to 6-membered ring with the nitrogen atom bonding them by forming C2-C5alkylene chain, in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and may be substituted with halogen atom, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy, phenyl, phenyl substituted with (Z)p1, oxo or thioxo,
    R27 is C1-C8alkyl, C1-C8alkyl arbitrarily substituted with R32, C3-C8cycloalkyl, C3-C8cycloalkyl arbitrarily substituted with R32, C3-C8alkenyl, C3-C8alkenyl arbitrarily substituted with R32, C3-C8alkynyl, C3-C8alkynyl arbitrarily substituted with R32, —SH, C1-C6alkylthio, C1-C6haloalkylthio, phenylthio, phenylthio substituted with (Z)p1, —CHO, —C(O)R33, —C(O)OR33, —C(O)SR33, —C(O)NHR34, —C(O)N(R34)R33, —C(O)C(O)R33, —C(O)C(O)OR33, —C(S)R33, —C(S)OR33, —C(S)SR33, —C(S)NHR34, —C(S)N(R34)R33, —P(O)(OR21)2, —P(S)(OR21)2, phenyl, phenyl substituted with (Z)p1, D-18, D-21, D-25, D-30 to D-35, D-47, D-50, D-51, E-3 to E-9, E-23 to E-31, E-34 or E-45,
    R28 is C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R32, C3-C8cycloalkyl, C3-C8cycloalkyl arbitrarily substituted with R32, C2-C6alkenyl C3-C8cycloalkyl, C2-C6haloalkenyl C3-C8cycloalkyl, C2-C8alkenyl, C2-C8alkenyl arbitrarily substituted with
    R32, C2-C8alkynyl, C2-C8alkynyl arbitrarily substituted with R32, phenyl, phenyl substituted with (Z)p1, D-1 to D-65 or E-1 to E-49,
    R28a is hydrogen atom or C1-C6alkyl,
    R29 is hydrogen atom, C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R32, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl, phenyl or phenyl substituted with (Z)p1, or R29 together with R28 may form 3- to 6-membered ring with the nitrogen atom bonding them by forming C2-C5alkylene chain, in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and may be arbitrarily substituted with halogen atom, C1-C6alkyl, C1-C6alkoxy, formyl, C1-C6alkylcarbonyl, C1-C6alkoxycarbonyl, phenyl or phenyl substituted with (Z)p1,
    R30 is C1-C8alkyl, C1-C8alkyl arbitrarily substituted with R32, C3-C8cycloalkyl, C3-C8alkenyl, C3-C8alkenyl arbitrarily substituted with R32, C3-C8alkynyl, C3-C8alkynyl arbitrarily substituted with R32,
    R31 is hydrogen atom, C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl C1-C4alkyl, C1-C6alkoxy C1-C4alkyl, C1-C6haloalkoxy C1-C4alkyl, C1-C6alkylthio C1-C4alkyl, C1-C6haloalkylthio C1-C4alkyl, C1-C6alkylsulfonyl C1-C4alkyl, C1-C6haloalkylsulfonyl C1-C4alkyl, phenyl C1-C4alkyl, phenyl C1-C4alkyl substituted with (Z)p1, C3-C6cycloalkyl, phenyl or phenyl substituted with (Z)p1, or R31 together with R30 may form 5- to 7-membered ring with the atom bonding them by forming C2-C4alkylene chain, in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and may be arbitrarily substituted with halogen atom, C1-C6alkyl or C1-C6haloalkyl,
    R32 is halogen atom, cyano, nitro, C3-C8cycloalkyl, C3-C8halocycloalkyl, —OH, —OR33, —OC(O)R33, —OC(O)OR33, —OC(O)NHR34, —OC(O)N(R34)R33, —OC(S)NHR34, —OC(S)N(R34)R33, —SH, —S(O)rR33, —SC(O)R33, —SC(O)OR33, —SC(O)NHR34, —SC(O)N(R34)R33, —SC(S)NHR34, —SC(S)N(R34)R33, —NHR34, —N(R34)R33, —N(R34)CHO, —N(R34)C(O)R33, —N(R34)C(O)OR33, —N(R34)C(O)NHR34, —N(R34)C(O)N(R34)R33, —N(R34)C(S)NHR34, —N(R34)C(S)N(R34)R33, —CHO, —C(O)R33, —C(O)OR33, —C(O)SR33, —C(O)NHR34, —C(O)N(R34)R33, —C(O)C(O)OR33, —Si(R13)(R14)R12, —P(O)(OR21)2, —P(S)(OR21)2, —P(phenyl)2, —P(O)(phenyl)2, phenyl, phenyl substituted with (Z)p1, D-1 to D-65 or E-4 to E-7, E10 to E-14, E-18, E-19, E-23 to E-28, E-32 to E-38, E-43, E-44 or E-45,
    R33 is C1-C6alkyl, C1-C6haloalkyl, C1-C4alkyl arbitrarily substituted with R35, C3-C6cycloalkyl, C3-C6halocycloalkyl, C2-C6alkenyl C3-C8cycloalkyl, C2-C6haloalkenyl C3-C8cycloalkyl, C2-C8alkenyl, C2-C8haloalkenyl, C3-C8cycloalkenyl, C3-C8halocycloalkenyl, C2-C8alkynyl, C2-C8haloalkynyl, phenyl, phenyl substituted with (Z)p1, D-1 to D-65, E-4 to E-7, E-23 to E-27 or E-28,
    R34 is hydrogen atom, C1-C6alkyl, C1-C6haloalkyl, C3-C8cycloalkyl, C3-C6alkenyl, C3-C6alkynyl, C1-C6alkylcarbonyl, C1-C6haloalkylcarbonyl, C1-C6alkoxycarbonyl, C1-C6haloalkoxycarbonyl, phenoxycarbonyl, phenoxycarbonyl substituted with (Z)p1, phenylcarbonyl, phenylcarbonyl substituted with (Z)p1, C1-C6alkylsulfonyl, C1-C6haloalkylsulfonyl, phenyl, phenyl substituted with (Z)p1, D-1 to D-4, D-6 to D-13, D-15 to D-23, D-25 to D-37, D-39, D-40, D-42, D-45 to D-60, D-62, D-63 or D-65, or R34 together with R33 may form 3- to 6-membered ring with the nitrogen atom bonding them by forming C2-C5alkylene chain, in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and may be arbitrarily substituted with halogen atom, C1-C6alkyl, C1-C6alkoxy, formyl, C1-C6alkylcarbonyl, C1-C6alkoxycarbonyl, phenyl or phenyl substituted with (Z)p1,
    R35 is cyano, C3-C6cycloalkyl, C3-C6halocylcoalkyl, E-4 to E-7, E-23 to E-28, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylthio, C1-C4haloalkylthio, C1-C4alkylsulfonyl, C1-C4haloalkylsulfonyl, C1-C6alkylcarbonyl, C1-C6haloalkylcarbonyl, C1-C6alkoxycarbonyl, di(C1-C6alkyl)aminocarbonyl, tri(C1-C6alkyl)silyl, phenyl, phenyl substituted with (Z)p1 or D-1 to D-65,
    m is an integer of 0 to 5,
    n is an integer of 0 to 4,
    p1 is an integer of 1 to 5,
    p2 is an integer of 0 to 4,
    p3 is an integer of 0 to 3,
    p4 is an integer of 0 to 2,
    p5 is an integer of 0 or 1,
    q1 is an integer of 0 to 3,
    q2 is an integer of 0 to 5,
    q3 is an integer of 0 to 7,
    q4 is an integer of 0 to 9,
    r is an integer of 0 to 2, and
    t is an integer of 0 or 1.
    (2) The isoxazoline-substituted benzamide compound or the salt thereof as set forth in (1), wherein
    G is an aromatic 6-membered ring shown in any one of G-1 to G-10 or an aromatic 5-membered ring shown in any one of G-11 to G-25
  • Figure US20150105398A1-20150416-C00017
    Figure US20150105398A1-20150416-C00018
    Figure US20150105398A1-20150416-C00019
  • X is halogen atom, cyano, nitro, —SF5, C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R4, C3-C8cycloalkyl, C3-C8cycloalkyl arbitrarily substituted with R4, C2-C6alkenyl, C2-C6alkenyl arbitrarily substituted with R4, C2-C6alkynyl, C2-C6alkynyl arbitrarily substituted with R4, —OH, —OR5, —OSO2R5, —S(O)rR5, —C(O)OR9, —C(O)SR9, —C(O)NHR10, —C(O)N(R10)R9, —C(S)OR9, —C(S)SR9, —C(S)NHR10, —C(S)N(R10)R9, —CH═NOR11, —C(R9)═NOR11, —S(O)2NHR10, —S(O)2N(R10)R9, —Si(R13)(R14)R12, phenyl, phenyl substituted with (Z)p1, D-1 to D-60 or E-1 to E-49, when m is an integer of 2 or more, each X may be identical with or different from each other,
    further, when two Xs are adjacent, the adjacent two Xs may form 5-membered or 6-membered ring together with carbon atoms to which the two Xs are bonded by forming —CH2CH2CH2—, —CH2CH2O—, —CH2OCH2—, —OCH2O—, —CH2CH2S—, —CH2SCH2—, —CH2CH2CH2CH2—, —CH2CH2CH2O—, —CH2CH2OCH2—, —CH2OCH2O—, —OCH2CH2O—, —OCH2CH2S— or —CH═CHCH═CH—, in this case, hydrogen atoms bonded to each carbon atom forming the ring may be arbitrarily substituted with halogen atom, C1-C4alkyl or C1-C4haloalkyl,
    Y is halogen atom, cyano, nitro, C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R4, —OR5, —OSO2R5, —S(O)rR5, —NHR7, —N(R7)R6, —N═CHOR8, —N═C(R9)OR8, —C(O)NHR10, —C(O)N(R10)R9, —C(S)NHR10, —C(S)N(R10)R9, phenyl, phenyl substituted with (Z)p1, D-1 to D-24, D-30 to D-38, D-43 to D-52 or D-53, when n is an integer of 2 or more,
    each Y may be identical with or different from each other,
    further, when two Ys are adjacent, the adjacent two Ys may form 5-membered or 6-membered ring together with carbon atoms to which the two Ys are bonded by forming —CH2CH2CH2—, —CH2CH2O—, —CH2OCH2—, —OCH2O—, —CH2CH2CH2CH2—, —CH2CH2CH2O—, —CH2CH2OCH2—, —CH2OCH2O—, —OCH2CH2O—, —OCH═N— or —SCH═N—, in this case, hydrogen atoms bonded to each carbon atom forming the ring may be arbitrarily substituted with halogen atom, C1-C4alkyl or C1-C4haloalkyl,
    R1 is C1-C8alkyl, C1-C8alkyl arbitrarily substituted with R16, C3-C8cycloalkyl, C3-C8halocycloalkyl, C3-C8alkenyl, C3-C8haloalkenyl, phenyl C3-C6alkenyl, phenyl C3-C6alkenyl substituted with (Z)p1, C3-C8alkynyl, C3-C8haloalkynyl, phenyl C3-C6alkynyl, phenyl C3-C6alkynyl substituted with (Z)p1, C1-C6alkoxy, —N(R20)R19, —N═CHR19b, —N═C(R19b)R19a, —C(O)N(R10)R9, —C(S)N(R10)R9, —C(═NR11)OR9, —C(═NR11)SR9, —C(═NR11)N(R10)R9, phenyl, phenyl substituted with (Z)p1, D-1 to D-4, D-6 to D-18, D-21 to D-24, D-26 to D-40, D-42, D-45 to D-58, E-4 to E-9, E-23 to E-28, E-30, E-31, E-34 or E-45,
    R2 is hydrogen atom, C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl C1-C4alkyl, C1-C4alkoxy C1-C4alkyl, C1-C4haloalkoxy C1-C4alkyl, benzyloxy C1-C4alkyl, C1-C4alkylthio C1-C4alkyl, C1-C4haloalkylthio C1-C4alkyl, C1-C4alkylsulfonyl C1-C4alkyl, C1-C4haloalkylsulfonyl C1-C4alkyl, phenylthio C1-C4alkyl, phenylthio C1-C4alkyl substituted with (Z)p1, cyano C1-C6alkyl, nitro C1-C6alkyl, C1-C4alkylcarbonyl C1-C4alkyl, C1-C4alkoxycarbony C1-C4alkyl, C3-C6cycloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, —SR9, —S(O)2R9, —SN(R15)R17, —OH, —OR19, —NHR20, —N(R20)R19, —N═CHR19b, —N═C(R19b)R19a, —C(O)R9, —C(O)OR9, —C(O)SR9, —C(S)OR9 or —C(S)SR9,
    or R1 and R2 together form ═C(R2a)R1a, and further R1 and R2 together may form 3- to 7-membered ring together with the nitrogen atom bonding them by forming O2 to C6 alkylene chain, in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and may be arbitrarily substituted with C1-C6alkyl, formyl, C1-C6alkylcarbonyl or C1-C6alkoxycarbonyl,
    R1a and R2a together may form 5- or 6-membered ring together with the carbon atom bonding them by forming C4 or C5 alkylene chain or C4 or C5 alkenylene chain, in this case, the alkylene chain and the alkenylene chain may contain one to three oxygen atoms, sulfur atoms or nitrogen atoms, and may be arbitrarily substituted with halogen atom or C1-C6alkyl,
    R3 is cyano, C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R4, C3-C8cycloalkyl, C3-C8halocycloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl, —OR5, —S(O)rR5, —N(R10)R9, —C(O)OR9, —C(O)SR9, —C(O)NHR10, —C(O)N(R10)R9, —C(S)OR9, —C(S)SR9, —C(S)NHR10, —C(S)N(R10)R9, —CH═NOR11, —C(R9)═NOR11, —Si(R13)(R14)R12, phenyl, phenyl substituted with (Z)p1, D-1 to D-4, D8- to D-13, D-15 to D-23, D-25 to D-37, D-39, D-40, D-42, D-45 to D-60 or E-4 to E-7, E-23 to E27 or E-28,
    R4 is halogen atom, cyano, C3-C6cycloalkyl, C3-C6halocycloalkyl, —OH, —OR5, —S(O)rR5, —N(R10)R9, —N(R10)C(O)R9, —N(R10)C(O)OR9, —N(R10)C(O)SR9, —N(R10)C(S)OR9, —N(R10)C(S)SR9, —N(R10)S(O)2R9, —Si(R13)(R14)R12, phenyl, phenyl substituted with (Z)p1, D-1 to D-5, D-8 to D-38, D-41, D-43, D-44, D-47 to D-52 or D-53,
    R5 is C1-C6alkyl, C1-C6haloalkyl, C1-C3haloalkoxy C1-C3haloalkyl, C3-C8cycloalkyl, C3-C8halocycloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl, phenyl, phenyl substituted with (Z)p1, D-1 to D-4, D-7, D-9, D-15 to D-23, D-30 to D-35, D-47 to D-53, E-3 to E-9, E-23 to E-27 or E-28,
    R6 is C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl C1-C4alkyl, C1-C4alkoxy C1-C4alkyl, C1-C4alkylthio C1-C4alkyl, —S(O)2R9, —CHO, —C(O)R9, —C(O)OR9, —C(O)SR9, —C(S)OR9 or —C(S)SR9,
    R7 is hydrogen atom, C1-C6alkyl, C1-C6haloalkyl, C3-C6alkenyl or C3-C6alkynyl,
    R8 is C1-C6alkyl,
    R9 is C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl C1-C4alkyl, C1-C6alkoxy C1-C4alkyl, C1-C6alkylthio C1-C4alkyl, cyano C1-C6alkyl, phenyl C1-C4alkyl, phenyl C1-C4alkyl substituted with (Z)p1, C3-C8cycloalkyl, C3-C8halocycloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl, phenyl, phenyl substituted with (Z)p1, D-1 to D-4, D-6 to D-35, D-38, D-47 to D-54 or D-55,
    R10 is hydrogen atom or C1-C6alkyl, or R10 together with R9 may form 5- to 7-membered ring with the nitrogen atom bonding them by forming C4-C6alkylene chain, in this case, the alkylene chain may contain one oxygen atom or sulfur atom,
    R11 is C1-C6alkyl, C1-C6haloalkyl, phenyl C1-C4alkyl, phenyl C1-C4alkyl substituted with (Z)p1, phenyl or phenyl substituted with (Z)p1, or R11 together with R9 may form 5- or 6-membered ring with the atom bonding them by forming C2-C3alkylene chain, in this case, the alkylene chain may be arbitrarily substituted with C1-C6alkyl,
    R12 is C1-C6alkyl, phenyl or phenyl substituted with (Z)p1,
    R13 and R14 independently of each other are C1-C6alkyl,
    R15 is C1-C6alkyl, C1-C6haloalkyl, phenyl C1-C4alkyl, phenyl C1-C4alkyl substituted with (Z)p1, phenyl or phenyl substituted with (Z)p1,
    R16 is halogen atom, cyano, C3-C6cycloalkyl, C3-C6halocycloalkyl, —OR25, —N(R26)R25, —SH, —S(O)rR27, —SO2NHR29, —SO2N(R29)R28, —CHO, —C(O)R28, —C(O)OR28, —C(O)NHR29, —C(O)N(R29)R28, —C(O)N(R29)OR28, —C(S)NHR29, —C(S)N(R29)R28, —C(R31)═NOH, —C(R31)═NOR30, —C(═NR31)OR30, —C(═NR31)SR30, —C(═NR31)N(R29)R30, —C(═NOR31)NHR29, —C(═NOR31)N(R29)R30, —Si(R13)(R14)R12, phenyl, phenyl substituted with (Z)p1, D-1 to D-60, E-1 to E-49 or M-1 to M-22,
    R17 is C1-C6alkyl, C1-C4alkoxy C1-C4alkyl, C1-C6alkoxycarbonyl C1-C4alkyl, phenyl C1-C4alkyl, phenyl C1-C4alkyl substituted with (Z)p, or C1-C6alkoxycarbonyl,
    R18 is C1-C6alkyl, phenyl C1-C4alkyl or phenyl C1-C4alkylsubstituted with (Z)p1, or R18 together with R17 may form 5- or 6-membered ring with the nitrogen atom bonding them by forming C4-C5alkylene chain, in this case, the alkylene chain may contain one oxygen atom or sulfur atom, and may be arbitrarily substituted with methyl or methoxy,
    R19 is C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R16, C3-C6cycloalkyl, C3-C6halocycloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, —CHO, —C(O)R28, —C(O)OR28, —C(O)NHR29, —C(O)N(R29)R28, —C(S)NHR29, —C(S)N(R29)R28, —S(O)2R28, —S(O)2NHR29, —S(O)2N(R29)R28, phenyl, phenyl substituted with (Z)p1, D-1 to D-13, D-15 to D-25, D-30 to D-37, D-39, D-40, D-42, D-45 to D-60, E-5, E-7, E-9, E-24, E-25, E-27, E-28, E-30 or E-31,
    R19a is C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl, phenyl, phenyl substituted with (Z)p1, D-1 to D-4, D-8 to D-10, D-15 to D-23, D-47 to D-55, E-4 to E-7, E-23 to E-27 or E-28,
    R19b is hydrogen atom or C1-C6alkyl, or R19a together with R19b may form 5- or 6-membered ring with the carbon atom bonding them by forming C4-C5alkylene chain, in this case, the alkylene chain may contain one oxygen atom or sulfur atom,
    R20 is hydrogen atom, C1-C6alkyl, C1-C6haloalkyl, C1-C4alkoxy C1-C4alkyl, C1-C4alkylthio C1-C4alkyl, cyano C1-C6alkyl, C1-C4alkoxycarbonyl C1-C4alkyl, C2-C6alkenyl, C3-C6alkynyl, —CHO, —C(O)R9, —C(O)OR9, —C(O)SR9, —C(S)OR9, —C(S)SR9 or C1-C6alkylsulfonyl,
    R22 is halogen atom, cyano, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy, C1-C6alkoxycarbonyl, —C(O)NH2 or —C(S)NH2, when q1, q2, q3 or q4 is an integer of 2 or more, each R22 may be identical with or different from each other, further in case where two R22s are present on the same carbon atom, the two R22s together may form oxo, thioxo, imino, C1-C6alkylimino, C1-C6alkoxyimino or C1-C6alkylidene,
    R23 is hydrogen atom, C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R32, C3-C6cycloalkyl, C3-C6alkenyl, C3-C6alkynyl, —OH, benzyloxy, —CHO, —C(O)R33, —C(O)OR33, —C(O)SR33, —C(O)NHR34, —C(O)N(R34)R33, —S(O)2R33, phenyl, phenyl substituted with (Z)p1 or D-5,
    R25 is hydrogen atom, C1-C6alkyl, C1-C6haloalkyl, C1-C4alkoxy C1-C4alkyl, C1-C4alkylthio C1-C4alkyl, cyano C1-C6alkyl, phenyl C1-C4alkyl, phenyl C1-C4alkyl substituted with (Z)p1, C3-C6alkenyl, C3-C6alkynyl, —CHO, —C(O)R33, —C(O)OR33, —C(O)SR33, —C(O)NHR34, —C(O)N(R34)R33, —C(S)R33, —C(S)OR33, —C(S)SR33, —C(S)NHR34, —C(S)N(R34)R33, —S(O)2R33, —S(O)2N(R34)R33, di(C1-C6alkyl)phosphoryl, di(C1-C6alkyl)thiophosphoryl, tri(C1-C4alkyl)silyl, phenyl or phenyl substituted with (Z)p1,
    R26 is hydrogen atom, C1-C6alkyl, C3-C6alkenyl, C3-C6alkynyl or C1-C6alkoxy, or R26 together with R25 may form 4- to 6-membered ring with the nitrogen atom bonding them by forming C3-C5alkylene chain, in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and may substituted with C1-C6alkyl, oxo or thioxo,
    R27 is C1-C6alklyl, C1-C6haloalkyl, hydroxy C1-C6alkyl, C1-C4alkoxy C1-C4alkyl, C1-C4alkylthio C1-C4alkyl, C1-C4alkylcarbonyl C1-C4alkyl, C1-C4alkoxycarbonyl C1-C4alkyl, di(C1-C4alkyl)aminocarbonyl C1-C4alkyl, tri(C1-C4alkyl)silyl C1-C4alkyl, phenyl C1-C4alkyl, phenyl C1-C4alkyl substituted with (Z)p1, C3-C6alkenyl, C3-C6alkynyl, C1-C6alkylcarbonyl, C1-C6alkylthio, phenylthio, phenylthio substituted with (Z)p1, —C(O)NHR34, —C(O)N(R34)R33, —C(S)NHR34, —C(S)N(R34)R33, phenyl, phenyl substituted with (Z)p1, D-21, D-35, D-47 or D-50,
    R28 is C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R32, C3-C6cycloalkyl, C3-C6halocycloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl, phenyl, phenyl substituted with (Z)p1, D-1 to D-60 or E-1 to E-49,
    R29 is hydrogen atom, C1-C6alkyl, C1-C4alkoxy C1-C4alkyl, C1-C4alkylthio C1-C4alkyl, cyano C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl, or R29 together with R28 may form 3- to 6-membered ring with the nitrogen atom bonding them by forming C2-C5alkylene chain, in this case, the alkylene chain may contain one oxygen atom or sulfur atom,
    R30 is C1-C6alkyl, C1-C4alkoxy C1-C4alkyl, C1-C4alkylthio C1-C4alkyl, C3-C6cycloalkyl C1-C4alkyl, tri(C1-C6alkyl)silyl C1-C4alkyl, phenyl C1-C4alkyl, phenyl C1-C4alkyl substituted with (Z)p1, C3-C8alkenyl, C3-C8haloalkenyl, C3-C8alkynyl or C3-C8haloalkynyl,
    R31 is hydrogen atom, C1-C6alkyl, C1-C6haloalkyl or C3-C6cycloalkyl, or R31 together with R30 may form 5- or 6-membered ring with the atom bonding them by forming
    C2-C3alkylene chain, in this case, the alkylene chain may be arbitrarily substituted with C1-C6alkyl,
    R32 is halogen atom, cyano, C3-C8cycloalkyl, C3-C8halocycloalkyl, —OR33, —OC(O)R33, —OC(O)NHR33, —OC(O)N(R34)R33, —S(O)rR33, —SC(O)R33, —SC(O)NHR33, —SC(O)N(R34)R33, —N(R34)CHO, —N(R34)C(O)R33, —N(R34)C(O)OR33, —C(O)OR33, —C(O)NHR34, —C(O)N(R34)R33, phenyl, phenyl substituted with (Z)p1, D-1 to D-60 or E-1 to E-49,
    R33 is C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl C1-C4alkyl, C1-C4alkoxy C1-C4alkyl, C1-C4haloalkoxy C1-C4alkylthio C1-C4haloalkylthio C1-C4alkylsulfonyl C1-C4alkyl, C1-C4haloalkylsulfonyl C1-C4alkyl, cyano C1-C6alkyl, phenyl C1-C4alkyl, phenyl C1-C4alkyl substituted with (Z)p1, C3-C6cycloalkyl, C3-C6halocycloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, phenyl, phenyl substituted with (Z)p1, D-1 to D-4, D-8 to D-13, D-15 to D-18, D-21, D-29 to D-37, D-47 to D-55, E-5, E-7, E-9, E-24, E-25, E-27, E-28, E-30, E-31 or E-34,
    R34 is hydrogen atom, C1-C6alkyl, C1-C6haloalkyl, C3-C6alkenyl or C3-C6alkynyl, or R34 together with R33 may form 3- to 6-membered ring with the nitrogen atom bonding them by forming C2-C5alkylene chain, in this case, the alkylene chain may contain one oxygen atom or sulfur atom.
    (3) The isoxazoline-substituted benzamide compound or the salt thereof as set forth in (2), wherein
    • G is G-1, G-3, G-4, G-13, G-14, G-17, G-18, G-20, G-21 or G-22,
  • X is halogen atom, cyano, nitro, —SF5, C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R4, C3-C8cycloalkyl, C3-C8halocycloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, —OR5, —OSO2R5, —S(O)rR5, —C(O)OR9, —C(O)SR9, —C(S)OR9, —C(S)SR9, —C(S)NHR10, —C(S)N(R10)R9, —CH═NOR11, —C(R9)═NOR11, —Si(R13)(R14)R12, E-10, E-12, E-18, E-32, E-35 or E-43, when m is 2 or 3, each X may be identical with or different from each other,
    further, when two Xs are adjacent, the adjacent two Xs may form 5-membered or 6-membered ring together with carbon atoms to which the two Xs are bonded by forming —CF2OCF2—, —OCF2O—, —CF2OCF2O— or —OCF2CF2O—,
    Y is halogen atom, cyano, nitro, C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R4, —OR5, —OSO2R5, —S(O)rR5, —NHR7, —N(R7)R6, —N═C(R9)OR8, —C(O)NH2 or —C(S)NH2, when n is 2 or 3, each Y may be identical with or different from each other,
    R1 is C1-C8alkyl, C1-C6alkyl arbitrarily substituted with R16, C3-C8cycloalkyl, C3-C8halocycloalkyl, C3-C3alkenyl, C3-C8haloalkenyl, C3-C8alkynyl, C3-C8haloalkynyl, —N(R20)R19, —C(O)N(R10)R9, —C(S)N(R10)R9, phenyl substituted with (Z)p1, D-8 to D-18, D-21 to D-24, D-26 to D-40, D-42, D-45 to D-58, E-4, E-5, E-7, E-8, E-9, E-23 to E-25, E-27, E-28, E-30, E-31 or E-34,
    R2 is hydrogen atom, C1-C6alkyl, C1-C6haloalkyl, C1-C4alkoxy C1-C4alkyl, C1-C4alkylthio C1-C4alkyl, cyano C1-C6alkyl, C3-C6cycloalkyl, C3-C6alkenyl, C3-C6alkynyl, —OH, C1-C6alkoxy, C1-C6alkylcarbonyloxy, C1-C6alkoxycarbonyloxy, C1-C6alkylsulfonyloxy, C1-C6haloalkylthio, phenylthio, phenylthio substituted with (Z)p1, C1-C6alkylsulfonyl, —SN(R18)R17, —NHR20, —N═CHR19b, —N═C(R19b)R19a, —C(O)R9, —C(O)OR9, —C(O)SR9, —C(S)OR9 or —C(S)SR9, or R2 together with R1 may form 3- to 7-membered ring with the nitrogen atom bonding them by forming C2-C6alkylene chain, in this case, the alkylene chain may contain one oxygen atom or sulfur atom,
    R3 is C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl C1-C4alkyl, C3-C6halocycloalkyl C1-C4alkyl, C1-C4alkoxy C1-C4alkyl, C1-C4haloalkoxy C1-C4alkyl, C1-C4alkylthio C1-C4alkyl, C1-C4alkylsulfinyl C1-C4alkyl, C1-C4alkylsulfonyl C1-C4alkyl, C1-C4haloalkylthio C1-C4alkyl, C1-C4haloalkylsulfinyl C1-C4alkyl, C1-C4haloalkylsulfonyl C1-C4alkyl, cyano C1-C6alkyl, C1-C4alkoxy C1-C4haloalkyl, C1-C4haloalkoxy C1-C4haloalkyl, C1-C4alkylthio C1-C4haloalkyl, C1-C4alkylsulfinyl C1-C4haloalkyl, C1-C4alkylsulfonyl C1-C4haloalkyl, C1-C4haloalkylthio C1-C4haloalkyl, C1-C4haloalkylsulfinyl C1-C4haloalkyl, C1-C4haloalkylsulfonyl C1-C4haloalkyl, cyano C1-C6haloalkyl, C3-C8cycloalkyl, C3-C8halocycloalkyl, E-4 to E-7, E-23 to E-27 or E-28,
    R4 is halogen atom, cyano, —OH, C1-C6alkoxy, C1-C6haloalkoxy, C1-C6alkylthio, C1-C6haloalkylthio, C1-C6alkylsulfinyl, C1-C6haloalkylsulfinyl, C1-C6alkylsulfonyl, C1-C6haloalkylsulfonyl or tri(C1-C6alkyl)silyl,
    R5 is C1-C6alkyl, C1-C6haloalkyl, C1-C3haloalkoxy C1-C3haloalkyl, C3-C8cycloalkyl, C3-C8halocycloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl, E-4 to E-9, E-23 to E-27 or E-28,
    R6 is C1-C6alkyl, C1-C6haloalkyl, —S(O)2R9, —CHO, —C(O)R9, —C(O)OR9, —C(O)SR9, —C(S)OR9 or —C(S)SR9,
    R7 is hydrogen atom, C1-C6alkyl or C1-C6haloalkyl,
    R9 is C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl C1-C4alkyl, C1-C6alkoxy C1-C4alkyl, C1-C6alkylthio C1-C4alkyl, cyano C1-C6alkyl, phenyl C1-C4alkyl, C3-C8cycloalkyl, C3-C8halocycloalkyl, C3-C6alkenyl or C3-C6alkynyl,
    R10 is hydrogen atom or C1-C6alkyl, or R10 together with R9 may form 5- or 6-membered ring with the nitrogen atom bonding them by forming C4 or C5alkylene chain, in this case, the alkylene chain may contain one oxygen atom or sulfur atom,
    R11 is C1-C6alkyl or C1-C6haloalkyl, or R11 together with R9 may form 5- or 6-membered ring with the atom bonding them by forming C2 or C3alkylene chain, in this case, the alkylene chain may be arbitrarily substituted with C1-C6alkyl,
    R15 is C1-C6alkyl or C1-C6haloalkyl,
    R16 is halogen atom, cyano, C3-C6cycloalkyl, C3-C6halocycloalkyl, —OR25, —N(R26)R25, —S(O)rR27, —SO2NHR29, —SO2N(R29)R28, —CHO, —C(O)R28, —C(O)OR28, —C(O)NHR29, —C(O)N(R29)R28, —C(O)N(R29)OR28, —C(S)NHR29, —C(S)N(R29)R28, —C(R31)=NOH, —C(R31)=NOR30, —C(═NR31)OR30, —C(═NR31)SR30, —C(═NR31)N(R29)R30, —C(═NOR31)NHR29, —C(═NOR31)N(R29)R30, phenyl, phenyl substituted with (Z)p1, D-1 to D-4, D-8 to D-42, D-47 to D-55, E-4 to E-12, E-14, E-16 to E-19, E-21 to E-23, E-26 to E-35, E-40 to E-45, E-48, M-2, M-3, M-5, M-8 to M-10, M-14, M-15 or M-16,
    R17 is C1-C6alkyl, C1-C6alkoxycarbonyl C1-C4alkyl or C1-C6alkoxycarbonyl,
    R18 is C1-C6alkyl or benzyl,
    R19 is C1-C6alkyl, C1-C6haloalkyl, C3-C6cyclaolakyl C1-C6alkyl, phenyl C1-C6alkyl, phenyl C1-C6alkyl substituted with (Z)p1, C3-C6cycloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, —C(O)R28, —C(O)OR28, —C(O)NHR29, —C(O)N(R29)R28, —C(S)NHR29, —C(S)N(R29)R28, C1-C6alkylsulfonyl, C1-C6haloalkylsulfonyl, phenylsulfonyl, phenylsulfonyl substituted with (Z)p1, phenyl, phenyl substituted with (Z)p1, D-1 to D-4, D-18, D-21, D-25, D-30 to D-35, D-47 to D-55 or D-56,
    R19a is C1-C6alkyl,
    R19b is hydrogen atom or C1-C6alkyl,
    R20 is hydrogen atom, C1-C6alkyl, C1-C4alkoxy C1-C4alkyl, C1-C4alkylthio C1-C4alkyl, cyano C1-C6alkyl, C3-C6alkenyl, C3-C6alkynyl, —CHO, C1-C6alkylcarbonyl, C1-C6haloalkylcarbonyl, C1-C6alkoxycarbonyl, C1-C6haloalkoxycarbonyl or C1-C6alkylsulfonyl,
    R22 is C1-C4alkyl or C1-C4haloalkyl, or two R22s present on the same carbon atom may together form oxo, or thioxo,
    R23 is hydrogen atom, C1-C6alkyl, —CHO, C1-C6alkylcarbonyl, C1-C6haloalkylcarbonyl, C1-C6alkoxycarbonyl, C1-C6alkylsulfonyl or C1-C6haloalkylsulfonyl,
    R25 is hydrogen atom, C1-C6alkyl, C1-C6haloalkyl, —C(O)R33, —C(O)OR33, —C(O)SR33, —C(O)NHR34, —C(O)N(R34)R33, —C(S)R33, —C(S)OR33, —C(S)SR33, —C(S)NHR34, —C(S)N(R34)R33, —S(O)2R33, —S(O)2N(R34)R33, di(C1-C6alkyl)thiophosphoryl, phenyl or phenyl substituted with (Z)p1,
    R26 is hydrogen atom or C1-C6alkyl, or R26 together with R25 may form 4- to 6-membered ring with the nitrogen atom bonding them by forming C3-C5alkylene chain, in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and may be substituted with C1-C6alkyl, oxo or thioxo,
    R27 is C1-C6alkyl, C1-C6haloalkyl, tri(C1-C4alkyl)silyl C1-C4alkyl, C1-C6alkylthio, —C(O)NHR34, —C(O)N(R34)R33, —C(S)NHR34, —C(S)N(R34)R33, phenyl, phenyl substituted with (Z)p1, D-47 or D-50,
    R28 is C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R32, C3-C6cycloalkyl, C3-C6halocycloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl, phenyl or phenyl substituted with (Z)p1,
    R29 is hydrogen atom, C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl, or R29 together with R28 may form 3- to 6-membered ring with the nitrogen atom bonding them by forming C2-C5alkylene chain, in this case, the alkylene chain may contain one oxygen atom or sulfur atom,
    R30 is C1-C6alkyl, C3-C6cycloalkyl C1-C4alkyl, phenyl C1-C4alkyl, phenyl C1-C4alkyl substituted with (Z)p1, C3-C8alkenyl or C3-C8alkynyl,
    R31 is hydrogen atom or C1-C6alkyl, or R31 together with R30 may form 5- or 6-membered ring with the atom bonding them by forming O2 or C3alkylene chain, in this case, the alkylene chain may be arbitrarily substituted with C1-C6alkyl,
    R32 is halogen atom, cyano, C3-C6cycloalkyl, C3-C6halocycloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylthio, C1-C4haloalkylthio, C1-C4alkoxycarbonyl, —C(O)NH2, C1-C4alkylaminocarbonyl, di(C1-C4alkyl)aminocarbonyl, phenyl or phenyl substituted with (Z)p1,
    R33 is C1-C6alkyl, C1-C6haloalkyl, C1-C4alkoxy C1-C4alkyl, C1-C4alkylthio C1-C4alkyl, C1-C4alkylsulfonyl C1-C4alkyl, phenyl C1-C4alkyl, phenyl C1-C4alkyl substituted with (Z)p1, C3-C6cycloalkyl, C3-C6halocycloalkyl, O3—C6alkenyl, C3-C6alkynyl, phenyl or phenyl substituted with (Z)p1,
    R34 is hydrogen atom or C1-C6alkyl,
    m is an integer of 1 to 3,
    n is an integer of 0 to 2,
    q1 is 0,
    q2 is an integer of 0 to 3,
    q3 is an integer of 0 to 2, and
    q4 is an integer of 0 to 2.
    (4) The isoxazoline-substituted benzamide compound or the salt thereof as set forth in (3), wherein
    A1 is carbon atom or nitrogen atom,
    A2 and A3 are carbon atom,
    • G is G-1,
  • X is halogen atom, cyano, nitro, —SF5, C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R4, C3-C8cycloalkyl, C3-C3halocycloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, —OR5, —OSO2R5, —S(O)rR5 or tri(C1-C8alkyl)silyl, when m is 2 or 3, each X may be identical with or different from each other, further, when two Xs are adjacent, the adjacent two Xs may form 5-membered or 6-membered ring together with carbon atoms to which the two Xs are bonded by forming —CF2OCF2—, —OCF2O—, —CF2OCF2O— or —OCF2CF2O—,
    Y is halogen atom, cyano, nitro, C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R4, —OR5, —OSO2R5, —S(O)rR5, —NHR7, —N(R7)R6, —C(O)NH2 or —C(S)NH2, when n is 2 or 3, each Y may be identical with or different from each other,
    R1 is C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R16, C3-C6cycloalkyl, C3-C6halocycloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl, —N(R20)R19, —C(O)N(R10)R9, —C(S)N(R10)R9, phenyl substituted with (Z)p1, D-8, D-10, D-11, D-13 to D-15, D-17, D-18, D-21 to D-23, D-26 to D-37, D-39, D-40, D-42, D-45, D-47 to D-54, D-56, D-58, E-4, E-5, E-7 or E-9,
    R2 is hydrogen atom, C1-C6alkyl, C1-C4alkoxy C1-C4alkyl, C1-C4alkylthio C1-C4alkyl, cyano C1-C6alkyl, C3-C6cycloalkyl, C3-C6alkenyl, C3-C6alkynyl, —OH, C1-C6alkylcarbonyloxy, C1-C6alkylsulfonyloxy, —NH2, —C(O)R9, —C(O)OR9, —C(O)SR9, —C(S)OR9 or —C(S)SR9,
    R3 is C1-C6haloalkyl, C1-C4alkoxy C1-C4haloalkyl, C1-C4haloalkoxy C1-C4haloalkyl, C1-C4alkylthio C1-C4haloalkyl, C1-C4haloalkylthio C1-C4haloalkyl, cyano C1-C6haloalkyl or C3-C8halocycloalkyl,
    R4 is halogen atom, cyano, —OH, C1-C6alkoxy, C1-C6haloalkoxy, C1-C6alkylthio, C1-C6haloalkylthio, C1-C6alkylsulfinyl, C1-C6haloalkylsulfinyl, C1-C6alkylsulfonyl, C1-C6haloalkylsulfonyl or tri(C1-C6alkyl)silyl,
    R5 is C1-C6alkyl, C1-C6haloalkyl, C1-C3haloalkoxy C1-C3haloalkyl, C3-C8cycloalkyl, C3-C8halocycloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C3-C6alkynyl or C3-C6haloalkynyl,
    R6 is C1-C6alkyl, C1-C6haloalkyl, —CHO, C1-C6alkylcarbonyl, C1-C6haloalkylcarbonyl, C3-C6cycloalkylcarbonyl, C3-C6halocycloalkylcarbonyl, C1-C6alkoxycarbonyl, C1-C6haloalkoxycarbonyl, C1-C6alkylthiocarbonyl, C1-C6alkoxythiocarbonyl, C1-C6alkyldithiocarbonyl, C1-C6alkylsulfonyl or C1-C6haloalkylsulfonyl,
    R7 is hydrogen atom or C1-C6alkyl,
  • R9 is C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl C1-C4alkyl, C1-C6alkoxy C1-C4alkyl, C1-C6alkylthio C1-C4alkyl, cyano C1-C6alkyl, C3-C8cycloalkyl, C3-C6alkenyl or C3-C6alkynyl,
  • R16 is halogen atom, cyano, C3-C6cycloalkyl, C3-C6halocycloalkyl, —OR25, —N(R26)R25, —S(O)rR27, —SO2NHR29, —SO2N(R29)R28, —C(O)R28, —C(O)OR28, —C(O)NHR29, —C(O)N(R29)R28, —C(O)N(R29)OR28, —C(S)NHR29, —C(S)N(R29)R28, —C(R31)═NOH, —C(R31)═NOR30, —C(═NR31)OR30, —C(═NR31)SR30, phenyl, phenyl substituted with (Z)p1, D-1 to D-4, D-8 to D-38, D-47 to D-55, E-4 to E-12, E-18, E-19, E-32, E-35, E-43, M-2, M-3, M-5, M-8, M-9 or M-10,
    R19 is C1-C6haloalkyl, C3-C6cycloalkyl, —C(O)R28, —C(O)OR28, —C(O)NHR29, —C(O)N(R29)R28, —C(S)NHR29, —C(S)N(R29)R28, phenyl, phenyl substituted with (Z)p1, D-3, D-4, D-21, D-47, D-50, D-51, D-53 or D-54,
    R20 is hydrogen atom, C1-C6alkyl, C1-C4alkoxy C1-C4alkyl, C1-C4alkylthio C1-C4alkyl, cyano C1-C6alkyl, C3-C6alkenyl, C3-C6alkynyl, —CHO, C1-C6alkylcarbonyl, C1-C6alkoxycarbonyl or C1-C6alkylsulfonyl,
    R25 is C1-C6alkyl, C1-C6haloalkyl, C1-C6alkylcarbonyl, C1-C6alkoxycarbonyl, C1-C6alkylaminocarbonyl, di(C1-C6alkyl)aminocarbonyl or C1-C6alkylsulfonyl,
    R26 is hydrogen atom or C1-C6alkyl,
    R27 is C1-C6alkyl, C1-C6haloalkyl or tri(C1-C4alkyl)silyl C1-C4alkyl,
    R28 is C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl C1-C4alkyl, C1-C4alkoxy C1-C4alkyl, C1-C4alkylthio C1-C4alky, cyano C1-C6alkyl, phenyl C1-C4alkyl, phenyl C1-C4alkyl substituted with (Z)p1, C3-C6cycloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, phenyl or phenyl substituted with (Z)p1,
    R29 is hydrogen atom, C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl, R30 is C1-C6alkyl or C3-C6cycloalkyl C1-C4alkyl,
    R31 is hydrogen atom or C1-C6alkyl, or R31 together with R30 may form 5- or 6-membered ring with the atom bonding them by forming O2 or C3alkylene chain.
    (5) The isoxazoline-substituted benzamide compound or the salt thereof as set forth in (4), wherein
    X is halogen atom, cyano, nitro, —SF5, C1-C6alkyl, C1-C6haloalkyl, hydroxy C1-C6haloalkyl, C1-C6alkoxy C1-C6haloalkyl, C1-C6haloalkoxy C1-C6haloalkyl, C3-C8halocycloalkyl, —OR5, —OSO2R5 or —S(O)rR5, when m is 2 or 3, each X may be identical with or different from each other,
    Y is halogen atom, cyano, nitro, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C6alkylthio, C1-C6haloalkylthio, C1-C6alkylsulfonyl, C1-C6haloalkylsulfonyl, —NHR7 or —N(R7)R6,
    R1 is C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R16, C3-C6cycloalkyl, E-4, E-5, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, —N(R20)R19, D-8, D-10, D-13 to D-15, D-18, D-21, D-34, D-35, D-47, D-48, D-50 to D-53 or D-54,
    R2 is hydrogen atom, C1-C6alkyl, C1-C4alkoxy C1-C4alkyl, cyano C1-C6alkyl, C3-C6alkynyl, —C(O)R9 or —C(O)OR9,
    R3 is C1-C6haloalkyl or C3-C8halocycloalkyl,
    R5 is C1-C6alkyl, C1-C6haloalkyl or C1-C3haloalkoxy C1-C3haloalkyl,
    R6 is C1-C6alkyl, —CHO, C1-C6alkylcarbonyl, C1-C6haloalkylcarbonyl, C1-C6alkoxycarbonyl, C1-C6alkylthiocarbonyl, C1-C6alkoxythiocarbonyl, C1-C6alkyldithiocarbonyl, C1-C6alkylsulfonyl or C1-C6haloalkylsulfonyl,
    R9 is C1-C6alkyl, C1-C6alkoxy C1-C4alkyl, C1-C6alkylthio C1-C4alkyl, C3-C3cycloalkyl, C3-C6alkenyl or C3-C6alkynyl,
    R16 is halogen atom, cyano, C3-C6cycloalkyl, C3-C6halocycloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, C1-C6alkylthio, C1-C6haloalkylthio, C1-C6alkylsulfinyl, C1-C6haloalkylsulfinyl, C1-C6alkylsulfonyl, C1-C6haloalkylsulfonyl, C1-C6alkylcarbonyl,
    —C(O)OR28, —C(O)NHR29, —C(O)N(R29)R28, —C(S)NH2, —C(R31)═NOH, —C(R31)═NOR30, phenyl, phenyl substituted with (Z)p1, D-1 to D-4, D-8 to D-38, D-47 to D-55, E-4 to E-7, E-10, E-11 or E-32,
    R19 is C1-C6haloalkyl, —C(O)R28, —C(O)OR28, phenyl, phenyl substituted with (Z)p1, D-3, D-4, D-21, D-47, D-50, D-51, D-53 or D-54,
    R20 is hydrogen atom or C1-C6alkyl,
    R28 is C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl C1-C4alkyl, C3-C6cycloalkyl, C3-C6alkenyl or C3-C6alkynyl,
    R29 is hydrogen atom or C1-C6alkyl,
    R30 is C1-C6alkyl,
    R31 is hydrogen atom or C1-C6alkyl, and
    n is an integer of 0 or 1.
    (6) 3,5-Bis (substituted aryl) substituted isoxazoline compound of formula (2) or a salt thereof:
  • Figure US20150105398A1-20150416-C00020
  • wherein
    A1 is carbon atom or nitrogen atom,
    X1 is halogen atom, —SF5, C1-C6haloalkyl, hydroxy C1-C6haloalkyl, C1-C6alkoxy C1-C6haloalkyl, C1-C6haloalkoxy C1-C6haloalkyl, C3-C8halocycloalkyl, C1-C6haloalkoxy, C1-C3haloalkoxy C1-C3haloalkoxy, C1-C6haloalkylthio, C1-C6haloalkylsulfinyl or C1-C6haloalkylsulfonyl, X2 is halogen atom, cyano, nitro, C1-C6alkyl, C1-C6haloalkyl, —OR5, —OSO2R5 or —S(O)rR5, when m1 is 2, each X2 may be identical with or different from each other,
    Y is halogen atom, cyano, nitro, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C6alkylthio, C1-C6haloalkylthio, C1-C6alkylsulfonyl, C1-C6haloalkylsulfonyl, —NHR7 or —N(R7)R6,
    R3 is C1-C6haloalkyl or C3-C8halocycloalkyl,
    R5 is C1-C6alkyl or C1-C6haloalkyl,
    R6 is C1-C6alkyl, —CHO, C1-C6alkylcarbonyl, C1-C6haloalkylcarbonyl, C1-C6alkoxycarbonyl, C1-C6alkylthiocarbonyl, C1-C6alkoxythiocarbonyl, C1-C6alkyldithiocarbonyl, C1-C6alkylsulfonyl or C1-C6haloalkylsulfonyl,
    R7 is hydrogen atom or C1-C6alkyl,
    R is halogen atom, cyano, nitro, —NH2, halosulfonyloxy, C1-C6alkylsulfonyloxy, C1-C6haloalkylsulfonyloxy, phenylsulfonyloxy, phenylsulfonyloxy substituted with (Z)p1 or —C(O)Ra,
    Ra is halogen atom, —OH, C1-C6alkoxy, 1-pyrazolyl, 1-imidazolyl or 1-triazolyl,
    Z is halogen atom, C1-C6alkyl or C1-C6haloalkyl, when p1 is an integer of 2 or more,
    each Z may be identical with or different from each other,
    m1 is an integer of 0 to 2,
    n is an integer of 0 or 1,
    p1 is an integer of 1 or 5, and
    r is an integer of 0 to 2.
    (7) 3,5-Bis (substituted aryl) substituted isoxazoline compound or the salt thereof as set forth in (6), wherein
    (a) in case where R is halosulfonyloxy, C1-C6haloalkylsulfonyloxy, phenylsulfonyloxy or phenylsulfonyloxy substituted with (Z)p1, Y is halogen atom, cyano, nitro, C1-C6alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C6alkylthio, C1-C6haloalkylthio, C1-C6alkylsulfonyl or C1-C6haloalkylsulfonyl,
    (b) in case where R is —C(O)Ra, Y is cyano, nitro, C1-C6alkyl, C1-C4haloalkyl, C1-C6haloalkylthio or C1-C6haloalkylsulfonyl,
    (c) in case where, R is halogen atom, cyano, nitro or —NH2, Y is cyano, C1-C6alkyl, C1-C6haloalkyl, C1-C6haloalkylthio or C1-C6haloalkylsulfonyl.
    (8) 4-Hydroxyiminomethyl substituted benzamide compound of formula (3) or a salt thereof:
  • Figure US20150105398A1-20150416-C00021
  • wherein
    A1 is carbon atom or nitrogen atom,
    J is hydrogen atom or halogen atom,
    W is oxygen atom or sulfur atom,
    Y is halogen atom, cyano, nitro, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C6alkylsulfonyl, C1-C6haloalkylsulfonyl or —N(R7)R6,
    R1 is C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R16, C3-C6cycloalkyl, E-4, E-5, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, —N(R20)R19, phenyl substituted with (Z)p1, D-8, D-10, D-13 to D-15, D-18, D-21, D-34, D-35, D-47, D-48, D-50 to D-53 or D-54,
    R2 is hydrogen atom, C1-C6alkyl, C1-C4alkoxy C1-C4alkyl, cyano C1-C6alkyl, C3-C6alkynyl, —C(O)R9 or —C(O)OR9,
    R6 is —CHO, C1-C6alkylcarbonyl, C1-C6haloalkylcarbonyl, C1-C6alkoxycarbonyl, C1-C6alkylthiocarbonyl, C1-C6alkoxythiocarbonyl, C1-C6alkyldithiocarbonyl, C1-C6alkylsulfonyl or C1-C6haloalkylsulfonyl,
    R7 is hydrogen atom or C1-C6alkyl,
    R9 is C1-C6alkyl, C1-C6alkoxy C1-C4alkyl, C1-C6alkylthio C1-C4alkyl, C3-C8cycloalkyl, C3-C6alkenyl or C3-C6alkynyl,
    R16 is halogen atom, cyano, C3-C6cycloalkyl, C3-C6halocycloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, C1-C6alkylsulfonyl, C1-C6haloalkylsulfonyl, C1-C6alkylcarbonyl, —C(O)OR28, —C(O)NHR29, —C(O)N(R29)R28, —C(S)NH2, —C(R31)═NOH, —C(R31)═NOR30, phenyl, phenyl substituted with (Z)p1, D-1 to D-4, D-8 to D-38, D-47 to D-55, E-4 to E-7, E-10, E-11 or E-32, D-1 to D-4, D-8 to D-38, D-47 to D-54 and D-55 are aromatic heterocyclic rings of the following formulae, respectively,
  • Figure US20150105398A1-20150416-C00022
    Figure US20150105398A1-20150416-C00023
    Figure US20150105398A1-20150416-C00024
    Figure US20150105398A1-20150416-C00025
  • Z is halogen atom, cyano, nitro, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, C1-C6alkylsulfonyl, C1-C6haloalkylsulfonyl, C1-C6alkoxycarbonyl, —C(O)NH2, C1-C6alkylaminocarbonyl, di(C1-C6alkyl)aminocarbonyl, —C(S)NH2, —S(O)2NH2, C1-C6alkylaminosulfonyl or di(C1-C6alkyl)aminosulfonyl, when p1, p2, p3 or p4 is an integer of 2 or more, each Z may be identical with or different from each other,
    R15 is C1-C6alkyl, phenyl or phenyl substituted with (Z)p1,
    E-4, E-5, E-10, E-11 or E-32 is a saturated heterocyclic ring of the following formulae, respectively
  • Figure US20150105398A1-20150416-C00026
  • R19 is C1-C6haloalkyl, —C(O)R28, —C(O)OR28, phenyl, phenyl substituted with (Z)p1, D-3, D-4, D-21, D-47, D-50, D-51, D-53 or D-54,
    R20 is hydrogen atom or C1-C6alkyl,
    R22 is C1-C4alkyl,
    R28 is C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl C1-C4alkyl, C3-C6cycloalkyl,
    C3-C6alkenyl or C3-C6alkynyl,
    R29 is hydrogen atom or C1-C6alkyl,
    R30 is C1-C6alkyl,
    R31 is C1-C6alkyl,
    n is an integer of 0 or 1, with a proviso that n is 1 when R1 and R2 are methyl at the same time,
    p1 is an integer of 1 to 5,
    p2 is an integer of 0 to 4,
    p3 is an integer of 0 to 3,
    p4 is an integer of 0 to 2,
    p5 is an integer of 0 or 1,
    q2 is an integer of 0 to 3, and
    q3 is an integer of 0 to 2
    (9) 4-Hydroxyiminomethyl substituted benzamide compound or the salt thereof as set forth in (8), wherein
    A1 is carbon atom,
    W is oxygen atom,
    Y is halogen atom, C1-C6alkyl or C1-C6haloalkyl,
    R1 is C1-C6alkyl arbitrarily substituted with R16, C3-C6cycloalkyl, E-4, E-5, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, D-13 to D-15, D-21, D-47, D-48, D-50 to D-53 or D-54,
    R16 is halogen atom, cyano, C3-C6cycloalkyl, E-4, E-5, E-10, C1-C6alkoxy, C1-C6haloalkoxy, C1-C6alkylsulfonyl, C1-C6haloalkylsulfonyl, —C(O)N(R29)R28, D-1, D-8, D-15 to D-17, D-21, D-22, D-28, D-29, D-34, D-35, D-38, D-47, D-50, D-51 or D-53.
    (10) Substituted alkenylbenzene compound of formula (4):
  • Figure US20150105398A1-20150416-C00027
  • wherein
    X1 is halogen atom, —SF5, C1-C6haloalkyl, hydroxy C1-C6haloalkyl, C1-C6alkoxy C1-C6haloalkyl, C3-C8halocycloalkyl, C1-C6haloalkoxy, C1-C3haloalkoxy C1-C3haloalkoxy, C1-C6haloalkylthio, C1-C6haloalkylsulfinyl or C1-C6haloalkylsulfonyl,
    X3 is hydrogen atom, halogen atom, cyano, nitro, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy or C1-C6alkylthio,
    X4 is hydrogen atom, halogen atom, cyano, C1-C4alkyl, C1-C4alkoxy or C1-C4haloalkoxy,
    • R3 is —C(R3a)(R3b)R3c,
  • R3a and R3b independently of each other are halogen atom, or R3a and R3b together may form 3- to 6-membered ring together with the carbon atom bonding them by forming C2-C6haloalkylene chain,
    R3c is hydrogen atom, halogen atom, C1-C6alkyl, C1-C5haloalkyl, C1-C4haloalkoxy or C1-C4haloalkylthio, with a proviso that in case where X1 is fluorine atom, chlorine atom or trifluoromethyl and both X2 and X3 are hydrogen atom, in case where both X1 and X2 are fluorine atom and X3 is hydrogen atom, and in case where both X1 and X2 are trifluoromethyl and X3 is hydrogen atom, R3c is hydrogen atom, chlorine atom, bromine atom, iodine atom, C1-C6alkyl, C1-C5haloalkyl, C1-C4haloalkoxy or C1-C4haloalkylthio.
    (11) The substituted alkenylbenzene compound as set forth in (10), wherein X1 is halogen atom, —SF5, C1-C6haloalkyl, C1-C6haloalkoxy or C1-C6haloalkylthio, X3 is hydrogen atom, halogen atom, cyano, nitro, C1-C6alkyl, C1-C6haloalkyl or C1-C6alkoxy,
    X4 is hydrogen atom or halogen atom,
    R3a and R3b are fluorine atom,
    R3c is hydrogen atom, fluorine atom, chlorine atom, bromine atom or trifluoromethyl, with a proviso that in case where X1 is fluorine atom, chlorine atom or trifluoromethyl and both X3 and X4 are hydrogen atom, in case where both X1 and X3 are fluorine atom and X4 is hydrogen atom, and in case where both X1 and X3 are trifluoromethyl and X4 is hydrogen atom, R3c is hydrogen atom, chlorine atom, bromine atom or trifluoromethyl.
    (12) A pesticide containing as an active ingredient one or more selected from isoxazoline-substituted benzamide compound and the salt thereof as set forth in (1) to (5)
    (13) An agrochemical containing as an active ingredient one or more selected from isoxazoline-substituted benzamide compound and the salt thereof as set forth in (1) to (5).
    (14) An endo- or ecto-parasiticide for mammals or birds containing as an active ingredient one or more selected from isoxazoline-substituted benzamide compound and the salt thereof as set forth in (1) to (5).
    (15) An insecticide or acaricide containing as an active ingredient one or more selected from isoxazoline-substituted benzamide compound and the salt thereof as set forth in (1) to (5).
    • Effect of the Invention
  • The compound according to the present invention has an excellent insecticidal and acaricidal activity for many agricultural insect pests, spider mites, endo- or ecto-parasiticide for mammals or birds, and exerts a control effect sufficient for pest insects that acquire resistance against exiting insecticides. Further, the compound has little adverse affect on mammals, fishes and beneficial insects, and has a low persistency and a low impact on the environment. Therefore, the present invention can provide a useful and novel pesticide.
    • BEST MODE FOR CARRYING OUT THE INVENTION
  • Active compounds used as the pesticide in the present invention are generally the compounds of formulae (1) to (5) mentioned above, and the compounds of formulae (6) to (11) mentioned above are novel production intermediates used for the production of these active compounds. These intermediates contain specific compounds themselves having control activity against specific pests that can be used as a control agent for the pest.
  • In the compounds included in the present invention, some compounds have geometrical isomers of E-form and Z-form depending on the kind of substituents. The present invention includes these E-forms, Z-forms and mixtures containing E-form and Z-form in an arbitrary proportion. In addition, the compounds included in the present invention have optically active forms resulting from the presence of 1 or more asymmetric carbon atoms, and the present invention includes all optically active forms or racemates. Further, in the compounds of formula (1) according to the present invention, some compounds wherein R2 is hydrogen atom are present in tautomer, and the present invention includes these structures,
  • Figure US20150105398A1-20150416-C00028
  • The compounds included in the present invention can be converted to acid addition salts for example salts of hydrohalide acid such as hydrofluoric acid, hydrochloric acid, hydrobromic acid, hydriodic acid or the like, salts of inorganic acids such as nitric acid, sulfuric acid, phosphoric acid, chloric acid, perchloric acid or the like, salts of sulfonic acid such as methansulfonic acid, ethansulfonic acid, trufluoromethansulfonic acid, benzene sulfonic acid, p-toluene sulfonic acid or the like, salts of carboxylic acid such as formic acid, acetic acid, propionic acid, trifluoroacetic acid, fumaric acid, tartaric acid, oxalic acid, maleic acid, malic acid, succinic acid, benzoic acid, mandelic acid, ascorbic acid, lactic acid, gluconic acid, citric acid or the like, or salts of amino acid such as glutamic acid, aspartic acid or the like, according to a conventional method.
  • The compounds included in the present invention can be converted to matal salts for example salts of alkali metal such as lithium, sodium, potassium, salts of alkaline earth metal such as calcium, barium, magnesium, or salts of aluminum, according to a conventional method.
  • Hereinafter, concrete examples of each substituent shown in the specification are described. In the specification, “n-” means normal, “i-” means iso, “s-” means secondary, and “t-” means tertiary, and “Ph” means phenyl.
  • Halogen atom in the compounds of the present invention includes fluororine atom, chlorine atom, bromine atom and iodine atom. In the interim, the indication of “halo” in the specification also means these halogen atoms.
  • In the specification, the indication of “Ca-Cbalkyl” means straight-chain or branched-chain hydrocarbon groups having carbon atom number of a to b, and includes for example methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, i-butyl, t-butyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1-ethylpropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, neopentyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1-ethylbutyl, 2-ethylbutyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, heptyl, 5-methylhexyl, 2-ethylpentyl, octyl, 2-ethylhexyl, nonyl, 2-methyloctyl, decyl, 2-methylnonyl, undecyl, 2-methyldecyl, dodecyl and the like. It is selected from the scope of the indicated carbon atom number.
  • In the specification, the indication of “Ca-Cbhaloalkyl” means straight-chain or branched-chain hydrocarbon groups having carbon atom number of a to b that a hydrogen atom (hydrogen atoms) bonded to carbon atom is (are) arbitrarily substituted with a halogen atom (halogen atoms). In this case, if it is substituted with two or more halogen atoms, these halogen atoms may be identical with or different from each other. Concrete examples thereof are for example fluoromethyl, chloromethyl, difluoromethyl, dichloromethyl, trifluoromethyl, chlorodifluoromethyl, trichloromethyl, bromodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2,2-difluoroethyl, 2-chloro-2-fluoroethyl, 2,2-dichloroethyl, 2-bromo-2-fluoroethyl, 2-bromo-2-chloroethyl, 2,2,2-trifluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, 2-bromo-2,2-difluoroethyl, 2-bromo-2-chloro-2-fluoroethyl, 2-bromo-2,2-dichloroethyl, pentafluoroethyl, 2-fluoropropyl, 2-chloropropyl, 2-bromopropyl, 2,3-dichloropropyl, 2,3-dibromopropyl, 3,3,3-trifluoropropyl, 3-bromo-3,3-difluoropropyl, 2,2,3,3-tetrafluoropropyl, 2-chloro-3,3,3-trifluoropropyl, 2,2,3,3,3-pentafluoropropyl, 2,2,2-trifluoro-1-trifluoromethylethyl, heptafluoropropyl, 1,2,2,2-tetrafluoro-1-trifluoromethylethyl, 2,2,3,3,4,4-hexafluorobutyl, 2,2,3,4,4,4-hexafluorobutyl, 2,2,3,3,4,4,4-heptafluorobutyl, nonafluorobutyl, 5-chloro-2,2,3,4,4,5,5-heptafluoropentyl, and the like. It is selected from the scope of the indicated carbon atom number.
  • In the specification, the indication of “cyano Ca-Cbalkyl” means straight-chain or branched-chain alkyl groups having carbon atom number of a to b that a hydrogen atom (hydrogen atoms) bonded to carbon atom is (are) arbitrarily substituted with a cyano group (cyano groups). Concrete examples thereof are for example cyanomethyl, 1-cyanoethyl, 2-cyanoethyl, 2-cyanopropyl, 3-cyanopropyl, 2-cyanobutyl, and the like. It is selected from the scope of the indicated carbon atom number.
  • In the specification, the indication of “Ca-Cbcycloalkyl” means cyclic hydrocarbon groups having carbon atom number of a to b, and can form 3-membered to 6-membered single ring or conjugated ring structure. In addition, each ring may be arbitrarily substituted alkyl group in the scope of the indicated carbon atom number. Concrete examples thereof are for example cyclopropyl, 1-methylcyclopropyl, 2-methylcyclopropyl, 2,2-dimethylcyclopropyl, 2,2,3,3-tetramethylcyclopropyl, cyclobutyl, cyclopentyl, 2-methylcyclopentyl, 3-methylcyclopentyl, cyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, bicyclo[2.2.1]heptan-2-yl and the like. It is selected from the scope of the indicated carbon atom number.
  • In the specification, the indication of “Ca-Cbhalocycloalkyl” means cyclic hydrocarbon groups having carbon atom number of a to b that a hydrogen atom (hydrogen atoms) bonded to carbon atom is (are) arbitrarily substituted with a halogen atom (halogen atoms), and can form 3-membered to 6-membered single ring or conjugated ring structure. In addition, each ring may be arbitrarily substituted alkyl group in the scope of the indicated carbon atom number. The substitution for halogen atom may be in the ring structure moiety, the side chain moiety or both of them. Further, if it is substituted with two or more halogen atoms, these halogen atoms may be identical with or different from each other. Concrete examples thereof are for example 2,2-dichlorocyclopropyl, 2,2-dibromocyclopropyl, 2,2-difluoro-1-methylcyclopropyl, 2,2-dichloro-1-methylcyclopropyl, 2,2-dibromo-1-methylcyclopropyl, 2,2-dichloro-3,3-dimethylcyclopropyl, 2,2,3,3-tetrafluorocyclobutyl, 2-trifluoromethylcyclohexyl, 3-trifluoromethylcyclohexyl, 4-trifluoromethylcyclohexyl and the like. It is selected from the scope of the indicated carbon atom number.
  • In the specification, the indication of “Ca-Cbalkenyl” means straight-chain or branched-chain unsaturated hydrocarbon groups having carbon atom number of a to b and having 1 or more double bonds. Concrete examples thereof are for example vinyl, 1-propenyl, 1-methylethenyl, 2-propenyl, 2-butenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 2-hexenyl, 2-methyl-2-pentenyl, 2,4-dimethyl-2,6-heptadienyl, 3,7-dimethyl-2,6-octadienyl, and the like. It is selected from the scope of the indicated carbon atom number.
  • In the specification, the indication of “Ca-Cbhalolkenyl” means straight-chain or branched-chain unsaturated hydrocarbon groups having carbon atom number of a to b and having 1 or more double bonds, which a hydrogen atom (hydrogen atoms) bonded to carbon atom is (are) arbitrarily substituted with a halogen atom (halogen atoms). In this case, if it is substituted with two or more halogen atoms, these halogen atoms may be identical with or different from each other. Concrete examples thereof are for example 2,2-dichlorovinyl, 2-fluoro-2-propenyl, 2-chloro-2-propenyl, 2-bromo-2-propenyl, 3-bromo-2-propenyl, 3,3-difluoro-2-propenyl, 2,3-dichloro-2-propenyl, 3,3-dichloro-2-propenyl, 2,3-dibromo-2-propenyl, 2,3,3-trifluoro-2-propenyl, 1-trifluoromethylvinyl, 2,3,3-trichloro-2-propenyl, 2-bromo-2-butenyl, 3-bromo-2-methyl-2-propenyl, 4,4-difluoro-3-butenyl, 3,4,4-trifluoro-3-butenyl, 3-chloro-4,4,4-trifluoro-2-butenyl, and the like. It is selected from the scope of the indicated carbon atom number.
  • In the specification, the indication of “Ca-Cbcycloalkenyl” means cyclic unsaturated hydrocarbon groups having carbon atom number of a to b and having 1 or more double bonds, and can form 3-membered to 6-membered single ring or conjugated ring structure. In addition, each ring may be arbitrarily substituted alkyl group in the scope of the indicated carbon atom number, and further the double bond may be either endo- or exo-form. Concrete examples thereof are for example 2-cyclopenten-1-yl, 3-cyclopenten-1-yl, 2-cyclohexen-1-yl, 3-cyclohexen-1-yl, bicyclo[2.2.1]-5-hepten-2-yl and the like. It is selected from the scope of the indicated carbon atom number.
  • In the specification, the indication of “Ca-Cbhaloycloalkenyl” means cyclic unsaturated hydrocarbon groups having carbon atom number of a to b and having 1 or more double bonds, which a hydrogen atom (hydrogen atoms) bonded to carbon atom is (are) arbitrarily substituted with a halogen atom (halogen atoms), and can form 3-membered to 6-membered single ring or conjugated ring structure. In addition, each ring may be arbitrarily substituted alkyl group in the scope of the indicated carbon atom number, and further the double bond may be either endo- or exo-form. The substitution for halogen atom may be in the ring structure moiety, the side chain moiety or both of them. Further, if it is substituted with two or more halogen atoms, these halogen atoms may be identical with or different from each other. Concrete examples thereof are for example 2-chlorobicyclo[2.2.1]-5-hepten-2-yl and the like. It is selected from the scope of the indicated carbon atom number.
  • In the specification, the indication of “Ca-Cbalkynyl” means straight-chain or branched-chain unsaturated hydrocarbon groups having carbon atom number of a to b and having 1 or more triple bonds. Concrete examples thereof are for example ethynyl, 1-propynyl, 2-propynyl, 1-methyl-2-propynyl, 2-butynyl, 2-pentynyl, 1-methyl-2-butynyl, 2-hexynyl, and the like. It is selected from the scope of the indicated carbon atom number.
  • In the specification, the indication of “Ca-Cbhalolkynyl” means straight-chain or branched-chain unsaturated hydrocarbon groups having carbon atom number of a to b and having 1 or more triple bonds, which a hydrogen atom (hydrogen atoms) bonded to carbon atom is (are) arbitrarily substituted with a halogen atom (halogen atoms). In this case, if it is substituted with two or more halogen atoms, these halogen atoms may be identical with or different from each other. Concrete examples thereof are for example 2-chloroethynyl, 2-bromoethynyl, 2-iodoethynyl, 3-chloro-2-propynyl, 3-bromo-2-propynyl, 3-iodo-2-propynyl, and the like. It is selected from the scope of the indicated carbon atom number.
  • In the specification, the indication of “Ca-Cbalkoxy” means alkyl-O— groups wherein the alkyl has carbon atom number of a to b, and includes for example methoxy, ethoxy, n-propyloxy, i-propyloxy, n-butyloxy, s-butyloxy, i-butyloxy, t-butyloxy, n-pentyloxy, n-hexyloxy and the like. It is selected from the scope of the indicated carbon atom number.
  • In the specification, the indication of “Ca-Cbhaloalkoxy” means haloalkyl-O— groups wherein the haloalkyl has carbon atom number of a to b, and includes for example difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2-chloro-1,1,2-trifluoroethoxy, 2-bromo-1,1,2-trifluoroethoxy, 2,2-dichloro-1,1,2-trifluoroethoxy, pentafluoroethoxy, 2,2,2-trichloro-1,1-difluoroethoxy, 2-bromo-1,1,2,2-tetrafluoroethoxy, 2,2,3,3-tetrafluoropropyloxy, 1,1,2,3,3,3-hexafluoropropyloxy, 2,2,2-trifluoro-1-trifluoromethylethoxy, heptafluoropropyloxy, 2-bromo-1,1,2,3,3,3-hexafluoropropyloxy, and the like. It is selected from the scope of the indicated carbon atom number.
  • In the specification, the indication of “Ca-Cbalkylthio” means alkyl-S— groups wherein the alkyl has carbon atom number of a to b, and includes for example methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, s-butylthio, i-butylthio, t-butylthio, n-pentylthio, n-hexylthio and the like. It is selected from the scope of the indicated carbon atom number.
  • In the specification, the indication of “Ca-Cbhaloalkylthio” means haloalkyl-S— groups wherein the haloalkyl has carbon atom number of a to b, and includes for example difluoromethylthio, trifluoromethylthio, bromodifluoromethylthio, 2,2,2-trifluoroethylthio, 1,1,2,2-tetrafluoroethylthio, 1,1,2-trifluoro-2-chloroethylthio, pentafluoroethylthio, 2-bromo-1,1,2,2-tetrafluoroethylthio, heptafluoropropylthio, 1,2,2,2-tetrafluoro-1-trifluoromethylthio, 1,2,2,2-tetrafluoro-1-trifluoroethylthio, nonafluorobutylthio, and the like. It is selected from the scope of the indicated carbon atom number.
  • In the specification, the indication of “Ca-Cbalkylsulfinyl” means alkyl-S(O)— groups wherein the alkyl has carbon atom number of a to b, and includes for example methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, i-propylsulfinyl, n-butylsulfinyl, s-butylsulfinyl, i-butylsulfinyl, t-butylsulfinyl, and the like. It is selected from the scope of the indicated carbon atom number.
  • In the specification, the indication of “Ca-Cbhaloalkylsulfinyl” means haloalkyl-S(O)— groups wherein the haloalkyl has carbon atom number of a to b, and includes for example difluoromethylsulfinyl, trifluoromethylsulfinyl, bromodifluoromethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, 2-bromo-1,1,2,2-tetrafluoroethylsulfinyl, 1,2,2,2-tetrafluoro-1-trifluoromethylethylsulfinyl, nonafluorobutylsulfinyl, and the like. It is selected from the scope of the indicated carbon atom number.
  • In the specification, the indication of “Ca-Cbalkylsulfonyl” means alkyl-SO2— groups wherein the alkyl has carbon atom number of a to b, and includes for example methanesulfonyl, ethanesulfonyl, n-propylsulfonyl, i-propylsulfonyl, n-butylsulfonyl, s-butylsulfonyl, i-butylsulfonyl, t-butylsulfonyl, n-pentylsulfonyl, n-hexylsulfonyl, and the like. It is selected from the scope of the indicated carbon atom number.
  • In the specification, the indication of “Ca-Cbhaloalkylsulfonyl” means haloalkyl-SO2— groups wherein the haloalkyl has carbon atom number of a to b, and includes for example difluoromethanesulfonyl, trifluoromethanesulfonyl, chlorodifluoromethanesulfonyl, bromodifluoromethanesulfonyl, 2,2,2-trifluoroethanesulfonyl, 1,1,2,2-tetrafluoroethanesulfonyl, 1,1,2-trifluoro-2-chloroethanesulfonyl, and the like. It is selected from the scope of the indicated carbon atom number.
  • In the specification, the indication of “Ca-Cbalkylamino” means amino groups, which either hydrogen atom is substituted with the above-mentioned alkyl group having carbon atom number of a to b, and includes for example methylamino, ethylamino, n-propylamino, i-propylamino, n-butylamino, i-butylamino, t-butylamino, and the like. It is selected from the scope of the indicated carbon atom number.
  • In the specification, the indication of “di(Ca-Cbalkyl)amino” means amino groups, which both hydrogen atoms are substituted with the above-mentioned alkyl groups having carbon atom number of a to b that may be identical with or different from each other, and includes for example dimethylamino, ethyl(methyl)amino, diethylamino, n-propyl(methyl)amino, i-propyl(methyl)amino, di(n-propyl)amino, n-butyl(methyl)amino, i-butyl(methyl)amino, t-butyl(methyl)amino, and the like. It is selected from the scope of the indicated carbon atom number.
  • In the specification, the indication of “Ca-Cbalkylcarbonyl” means alkyl-C(O)— groups wherein the alkyl has carbon atom number of a to b, and includes for example CH3C(O)—, CH3CH2C(O)—, CH3CH2CH2C(O)—, (CH3)2CHC(O)—, CH3(CH2)3C(O)—, (CH3)2CHCH2C(O)—, CH3CH2CH(CH3)C(O)—, (CH3)3CC(O)—, CH3(CH2)4C(O)—, CH3(CH2)5C(O)—, and the like. It is selected from the scope of the indicated carbon atom number.
  • In the specification, the indication of “Ca-Cbhaloalkylcarbonyl” means haloalkyl-C(O)— groups wherein the haloalkyl has carbon atom number of a to b, and includes for example FCH2C(O)—, ClCH2C(O)—, F2CHC(O)—, Cl2CHC(O)—, CF3C(O)—, CICF2C(O)—, BrCF2C(O)—, CCl3C(O)—, CF3CF2C(O)—, ClCH2CH2CH2C(O)—, CF3CF2CF2C(O)—, ClCH2C(CH3)2C(O)—, and the like. It is selected from the scope of the indicated carbon atom number.
  • In the specification, the indication of “Ca-Cbalkoxycarbonyl” means alkyl-O—C(O)— groups wherein the alkyl has carbon atom number of a to b, and includes for example CH3OC(O)—, CH3CH2OC(O)—, CH3CH2CH2OC(O)—, (CH3)2CHOC(O)—, CH3(CH2)3OC(O)—, (CH3)2CHCH2OC(O)—, (CH3)3COC(O)—, and the like. It is selected from the scope of the indicated carbon atom number.
  • In the specification, the indication of “Ca-Cbhaloalkoxycarbonyl” means haloalkyl-O—C(O)— groups wherein the haloalkyl has carbon atom number of a to b, and includes for example ClCH2CH2OC(O)—, CF3CH2OC(O)—, and the like. It is selected from the scope of the indicated carbon atom number.
  • In the specification, the indication of “Ca-Cbalkylaminocarbonyl” means carbamoyl groups, which either hydrogen atom is substituted with the above-mentioned alkyl group having carbon atom number of a to b, and includes for example CH3NHC(O)—, CH3CH2NHC(O)—, CH3CH2CH2NHC(O)—, (CH3)2CHNHC(O)—, CH3(CH2)3NHC(O)—, (CH3)2CHCH2NHC(O)—, CH3CH2CH(CH3)NHC(O)—, (CH3)3CNHC(O)—, and the like. It is selected from the scope of the indicated carbon atom number.
  • In the specification, the indication of “Ca-Cbhaloalkylaminocarbonyl” means carbamoyl groups, which either hydrogen atom is substituted with the above-mentioned haloalkyl group having carbon atom number of a to b, and includes for example 2-fluoroethylcarbamoyl, 2-chloroethylcarbamoyl, 2,2-difluorocarbamoyl, 2,2,2-trifluoroethylcarbamoyl, and the like. It is selected from the scope of the indicated carbon atom number.
  • In the specification, the indication of “di(Ca-Cbalkyl)aminocarbonyl” means carbamoyl groups, which both hydrogen atoms are substituted with the above-mentioned alkyl group having carbon atom number of a to b that may be identical with or different from each other, and includes for example (CH3)2NC(O)—, CH3CH2N(CH3)C(O)—, (CH3CH2)2NC(O)—, (CH3CH2CH2)2NC(O)—, (CH3CH2CH2CH2)2NC(O)—, and the like. It is selected from the scope of the indicated carbon atom number.
  • In the specification, the indication of “Ca-Cbalkylaminosulfonyl” means sulfamoyl groups, which either hydrogen atom is substituted with the above-mentioned alkyl group having carbon atom number of a to b, and includes for example CH3NHSO2—, CH3CH2NHSO2—, CH3CH2CH2NHSO2—, (CH3)2CHNHSO2—, CH3(CH2)3NHSO2—, (CH3)2CHCH2NHSO2—, CH3CH2CH(CH3)NHSO2—, (CH3)3CNHSO2, and the like. It is selected from the scope of the indicated carbon atom number.
  • In the specification, the indication of “di(Ca-Cbalkyl)aminosulfonyl” means sulfamoyl groups, which both hydrogen atoms are substituted with the above-mentioned alkyl group having carbon atom number of a to b that may be identical with or different from each other, and includes for example (CH3)2NSO2—, CH3CH2N(CH3)SO2—, (CH3CH2)2NSO2—, (CH3CH2CH2)2NSO2—, (CH3CH2CH2CH2)2NSO2—, and the like. It is selected from the scope of the indicated carbon atom number.
  • In the specification, the indication of “tri(Ca-Cbalkyl)silyl” means silyl groups substituted with the above-mentioned alkyl group having carbon atom number of a to b that may be identical with or different from each other, and includes for example trimethylsilyl, triethylsilyl, tri(n-propyl)silyl, ethyldimethylsilyl, n-propyldimethylsilyl, n-butyldimethylsilyl, i-butyldimethylsilyl, t-butyldimethylsilyl, and the like. It is selected from the scope of the indicated carbon atom number.
  • In the specification, the indication of “Ca-Cbalkylcarbonyloxy” means alkylcarbonyl-O— groups wherein the alkyl has carbon atom number of a to b, and includes for example CH3C(O)—O—, CH3CH2C(O)—O—, CH3CH2CH2C(O)—O—, (CH3)2CHC(O)—O—, CH3(CH2)3C(O)—O—, (CH3)2CHCH2C(O)—O—, CH3CH2CH(CH3)C(O)—O—, (CH3)3CC(O)—O—, and the like. It is selected from the scope of the indicated carbon atom number.
  • In the specification, the indication of “Ca-Cbalkylsulfonyloxy” means alkylsulfonyl-O— groups wherein the alkyl has carbon atom number of a to b, and includes for example CH3SO2—O—, CH3CH2SO2—O—, CH3CH2CH2SO2—O—, (CH3)2CHSO2—O—, and the like. It is selected from the scope of the indicated carbon atom number.
  • In the specification, the indication of “Ca-Cbhaloalkylsulfonyloxy” means haloalkylsulfonyl-O— groups wherein the haloalkyl has carbon atom number of a to b, and includes for example difluoromethanesulfonyl-O—, trifluoromethanesulfonyl-O—, chlorodifluoromethanesulfonyl-O—, bromodifluoromethanesulfonyl-O—, and the like. It is selected from the scope of the indicated carbon atom number.
  • In the specification, the indication of “Ca-Cbcycloalkyl Cd-Cealkyl”, “Ca-Cbhalocycloalkyl Cd-Cealkyl”, “Ca-Cbalkoxy Cd-Cealkyl”, “Ca-Cbhaloalkoxy Cd-Cealkyl”, “Ca-Cbalkylthio Cd-Cealkyl”, “Ca-Cbhaloalkylthio Cd-Cealkyl”, “Ca-Cbalkylsulfinyl Cd-Cealkyl”, “Ca-Cbhaloalkylsulfinyl Cd-Cealkyl”, “Ca-Cbalkylsulfonyl Cd-Cealkyl”, “Ca-Cbhaloalkylsulfonyl Cd-Cealkyl”, “Ca-Cbalkoxycarbonyl Cd-Cealkyl”, “phenyl Cd-Cealkyl” or “phenyl Cd-Cealkyl substituted with (Z)p1” means straight-chain or branched-chain hydrocarbon groups having carbon atom number of d to e, which a hydrogen atom (hydrogen atoms) bonded to carbon atom is (are) arbitrarily substituted with the Ca-Cbcycloalkyl, Ca-Cbhalocycloalkyl, Ca-Cbalkoxy, Ca-Cbhaloalkoxy, Ca-Cbalkylthio, Ca-Cbhaloalkylthio, Ca-Cbalkylsulfinyl, Ca-Cbhaloalkylsulfinyl, Ca-Cbalkylsulfonyl, Ca-Cbhaloalkylsulfonyl, Ca-Cbalkoxycarbonyl, phenyl or phenyl substituted with (Z)p1 that has the meaning mentioned above, respectively. It is selected from the scope of the indicated carbon atom number.
  • In the specification, the indication of “Ca-Cbalkyl arbitrarily substituted with R4”, “Ca-Cbalkyl arbitrarily substituted with R16”, “Ca-Cbalkyl arbitrarily substituted with R24”, “Ca-Cbalkyl arbitrarily substituted with R32”, or “Ca-Cbalkyl arbitrarily substituted with R35” means straight-chain or branched-chain hydrocarbon groups having carbon atom number of d to e, which a hydrogen atom (hydrogen atoms) bonded to carbon atom is (are) arbitrarily substituted with R4, R16, R24, R32 or R35. It is selected from the scope of the indicated carbon atom number.
  • In this case, when two or more substituents R4, R16, R24, R32 or R35 are present on the Ca-Cbalkyl, respective R4, R16R24, R32 or R35 may be identical with or different from each other.
  • In the specification, the indication of “hydroxy Cd-Cecycloalkyl”, “Ca-Cbalkoxy Cd-Cecycloalkyl”, “Ca-Cbalkenyl Cd-Cecycloalkyl” or “Ca-Cbhaloalkenyl Cd-Cecycloalkyl” means the cycloalkyl having carbon atom number of d to e, which a hydrogen atom (hydrogen atoms) bonded to carbon atom is (are) arbitrarily substituted with Ca-Cbalkoxy, Ca-Cbalkenyl, Ca-Cbhaloalkenyl or hydroxy. It is selected from the scope of the indicated carbon atom number.
  • In the specification, the indication of “Ca-Cbcycloalkyl arbitrarily substituted with R4”, “Ca-Cbcycloalkyl arbitrarily substituted with R16”, “Ca-Cbcycloalkyl arbitrarily substituted with R24” or “Ca-Cbcycloalkyl arbitrarily substituted with R32” means the cycloalkyl groups having carbon atom number of a to b, which a hydrogen atom (hydrogen atoms) bonded to carbon atom is (are) arbitrarily substituted with R4, R16, R24 or R32. The substitution for R4, R16, R24 or R32 may be in the ring structure moiety, the side chain moiety or both of them. In this case, when two or more substituents R4, R16, R24 or R32 are present on the Ca-Cbcycloalkyl, respective R4, R16, R24 or R32 may be identical with or different from each other.
  • In the specification, the indication of “phenyl Ca-Cbalkenyl” or “phenyl Ca-Cbalkenyl substituted with (Z)p1” means the alkenyl having carbon atom number of a to b, which a hydrogen atom (hydrogen atoms) bonded to carbon atom is (are) arbitrarily substituted phenyl or phenyl substituted with (Z)p1. It is selected from the scope of the indicated carbon atom number.
  • In the specification, the indication of “Ca-Cbalkenyl arbitrarily substituted with R4”, “Ca-Cbalkenyl arbitrarily substituted with R16”, “Ca-Cbalkenyl arbitrarily substituted with R24” or “Ca-Cbalkenyl arbitrarily substituted with R32” means the alkenyl groups having carbon atom number of a to b, which a hydrogen atom (hydrogen atoms) bonded to carbon atom is (are) arbitrarily substituted with R4, R16, R24 or R32. It is selected from the scope of the indicated carbon atom number. In this case, when two or more substituents R4, R16, R24 or R32 are present on the Ca-Cbalkenyl, respective R4, R16, R24 or R32 may be identical with or different from each other.
  • In the specification, the indication of “phenyl Ca-Cbalkynyl” or “phenyl Ca-Cbalkynyl substituted with (Z)p1” means the alkynyl having carbon atom number of a to b, which a hydrogen atom (hydrogen atoms) bonded to carbon atom is (are) arbitrarily substituted phenyl or phenyl substituted with (Z)p1. It is selected from the scope of the indicated carbon atom number.
  • In the specification, the indication of “Ca-Cbalkynyl arbitrarily substituted with R4”, “Ca-Cbalkynyl arbitrarily substituted with R16”, “Ca-Cbalkynyl arbitrarily substituted with R24” or “Ca-Cbalkynyl arbitrarily substituted with R32” means the alkynyl groups having carbon atom number of a to b, which a hydrogen atom (hydrogen atoms) bonded to carbon atom is (are) arbitrarily substituted with R4, R16, R24 or R32. It is selected from the scope of the indicated carbon atom number. In each other.
  • In the specification, concrete examples of the indication of “R1 and R2 together may form 3- to 8-membered ring together with the nitrogen atom bonding them by forming C2 to C7 alkylene chain, in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom”,
  • “R10 together with R9 may form 3- to 7-membered ring with the nitrogen atom bonding them by forming C2-C6alkylene chain, in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom”,
    “R18 together with R17 may form 5- to 8-membered ring with the nitrogen atom bonding them by forming C4-C7alkylene chain, in this case, the alkylene chain may contain one oxygen atom or sulfur atom”,
    “R26 together with R25 may form 3- to 6-membered ring with the nitrogen atom bonding them by forming C2-C5alkylene chain, in this case, the alkylene chain may contain one oxygen atom or sulfur atom”,
    “R29 together with R28 may form 3- to 6-membered ring with the nitrogen atom bonding them by forming C2-C5alkylene chain, in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom”,
    “R34 together with R33 may form 3- to 6-membered ring with the nitrogen atom bonding them by forming C2-C5alkylene chain, in this case, the alkylene chain may contain one oxygen atom or sulfur atom”, are for example aziridine, azetidine, pyrrolidine, oxazolidine, thiazoridine, imidazolidine, piperidine, morpholine, thiomorpholine, piperazine, homopiperidine, heptamethyleneimine, and the like. It is selected from the scope of the indicated carbon atom number.
  • In the specification, concrete examples of the indication of “R7 together with R6 may form 3- to 7-membered ring with the nitrogen atom bonding them by forming C2-C6alkylene chain, in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom” are for example aziridine, azetidine, azetidin-2-one, pyrrolidine, pyrrrolidin-2-one, oxazolidine, oxazolidin-2-one, thiazoridine, thiazoridin-2-one, imidazolidine, imidazolidin-2-one, piperidine, piperidin-2-one, morpholine, tetrahydro-1,3-oxadin-2-one, thiomorpholine, tetrahydro-1,3-thiazin-2-one, piperazine, tetrahydropyrimidin-2-one, homopiperidine, homopiperidin-2-one, and the like. It is selected from the scope of the indicated carbon atom number.
  • In the specification, concrete examples of the indication of “R11 together with R9 may form 5- to 7-membered ring with the atom bonding them by forming C2-C4alkylene chain, in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom” are for example isoxazoline, oxazoline, thiazoline, imidazoline, 1,4,2-dioxazoline, 1,4,2-oxathiazoline, 1,2,4-oxadiazoline, dihydro-1,2-oxadine, dihydro-1,3-oxadine, dihydro-1,3-thiazine, 3,4,5,6-tetrahydropyrimidine, dihydro-1,4,2-dioxadine, dihydro-1,4,2-oxathiazine, dihydro-4H-1,2,4-oxadiazine, tetrahydro-1,2-oxazepine, and the like. It is selected from the scope of the indicated carbon atom number.
  • In the specification, concrete examples of the indication of “R31 together with R30 may form 5- to 7-membered ring with the atom bonding them by forming C2-C4alkylene chain, in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom” are for example oxazoline, thiazoline, imidazoline, dihydro-1,3-oxazine, dihydro-1,3-thiazine, 3,4,5,6-tetrahydropyrimidine, dihydro-1,4,2-dioxadine, and the like. It is selected from the scope of the indicated carbon atom number.
  • In the compounds included in the present invention, the combination of the atoms of A1, A2 and A3 includes for example the following groups.
  • That is, A-I: A1, A2 and A3 are carbon atoms.
  • A-II: A1 is nitrogen atom, A2 and A3 are carbon atoms.
    A-III: A2 is nitrogen atom, A1 and A3 are carbon atoms.
    A-IV: A1 and A3 are nitrogen atom, A2 is carbon atom.
    A-V: A2 and A3 are nitrogen atom, A1 is carbon atom.
  • In the compounds included in the present invention, the substituent G includes for example aromatic 6-membered rings shown in any one of G-1 to G-10 and aromatic 5-membered rings shown in any one of G-11 to G-25. Among them, aromatic 6-membered rings shown in G-1, G-3 and G-4 and aromatic 5-membered rings shown in any one of G-13, G-14, G-17, G-18, G-20, G-21 and G-22 are preferable, and aromatic 6-membered ring shown in G-1 is particularly preferable.
  • In the compounds included in the present invention, the substituent W includes for example oxygen atom or sulfur atom.
  • In the compounds included in the present invention, the substituent X includes for example the following groups. In each case mentioned below, when m is an integer of 2 or more, Xs may be identical with or different from each other.
  • That is, X-I: halogen atom and C1-C6haloalkyl.
    X-II: halogen atom, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy, C1-C6alkylsulfonyloxy, C1-C6alkylthio, C1-C6alkylsulfinyl and C1-C6alkylsulfonyl.
    X-III: halogen atom, C1-C6haloalkyl, C1-C6haloalkoxy, C1-C3haloalkoxy C1-C3haloalkoxy, C1-C6haloalkylsulfonyloxy, C1-C6haloalklylthio, C1-C6haloalkylsulfinyl and C1-C6haloalkylsulfonyl.
    X-IV: halogen atom, C1-C6haloalkyl, cyano, nitro, —SF5 and —Si(R13)(R14)R12 wherein R12 is C1-C6alkyl, phenyl or phenyl substituted with (Z)p1, R13 and R14 independently of each other are C1-C6alkyl.
    X-V: halogen atom and C1-C6alkyl arbitrarily substituted with R4 wherein R4 is halogen atom, cyano, —OH, C1-C6alkoxy, C1-C6haloalkoxy, C1-C6alkylthio, C1-C6haloalkylthio, C1-C6alkylsulfinyl, C1-C6haloalkylsulfinyl, C1-C6alkylsulfonyl, C1-C6haloalkylsulfonyl or tri(C1-C6alkyl)silyl.
    X-VI: halogen atom, C1-C6haloalkyl, C3-C8cycloalkyl, C3-C8halocycloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, E-10, E-12, E-18, E-32, E-35 and E-43.
    X-VII: halogen atom, C1-C6haloalkyl, —OR5, —OSO2R5 and —S(O)rR5 wherein R5 is C1-C6alkyl, C1-C6haloalkyl, C1-C3haloalkoxy C1-C3haloalkyl, C3-C8cycloalkyl, C3-C8halocycloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl, E-4 to E-9, E-23 to E-27 or E-28, r is an integer of 0 to 2.
    X-VIII: halogen atom, C1-C6haloalkyl, —C(O)OR9, —C(O)SR9, —C(S)OR9, —C(S)SR9, —C(S)NHR10, —C(S)N(R10)R9, —CH═NOR11 and —C(R9)═NOR11 wherein R9 is C1-C6alkyl, C1-C6haloalkyl, C3-C8cycloalkyl or C3-C8halocycloalkyl, R10 is hydrogen atom or C1-C6alkyl, or R10 together with R9 may form 5- or 6-membered ring with the nitrogen atom bonding them by forming C4-C5alkylene chain, in this case, the alkylene chain may contain one oxygen atom or sulfur atom, R11 is C1-C6alkyl or C1-C6haloalkyl, or R11 together with R9 may form 5- or 6-membered ring with the atom bonding them by forming C2-C3alkylene chain, in this case, the alkylene chain may be arbitrarily substituted with C1-C6alkyl.
    X-IX: m is 2, two adjacent Xs form 5- or 6-membered ring with the carbon atom bonding them by forming —CF2OCF2—, —OCF2O—, —CF2OCF2O— or —OCF2CF2O—.
  • In the compounds included in the present invention, m indicating the number of substituent X is an integer of 0 to 5. Among them, m is preferably 1, 2 and 3.
  • In the compounds included in the present invention, the substituent Y includes for example the following groups. In each case mentioned below, when n is an integer of 2 or more, Ys may be identical with or different from each other.
  • That is, Y-I: halogen atom, C1-C6alkyl and C1-C6haloalkyl.
    Y-II: halogen atom, C1-C6alkyl, cyano, nitro, —C(O)NH2 and —C(S)NH2.
    Y-III: halogen atom, C1-C6alkyl and C1-C6alkyl arbitrarily substituted with C1-C6alkyl and R4 wherein R4 is halogen atom, cyano, —OH, C1-C6alkoxy, C1-C6haloalkoxy, C1-C6alkylthio, C1-C6haloalkylthio, C1-C6alkylsulfinyl, C1-C6haloalkylsulfinyl, C1-C6alkylsulfonyl, C1-C6haloalkylsulfonyl or tri(C1-C6alkyl)silyl.
    Y-IV: halogen atom, C1-C6alkyl, —OR5, —OSO2R5 and —S(O)rR5 wherein R5 is C1-C6alkyl, C1-C6haloalkyl, C1-C3haloalkoxy C1-C3haloalkyl, C3-C8cycloalkyl, C3-C8halocycloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl, E-4 to E-9, E-23 to E-27 or E-28, r is an integer of 0 to 2.
    Y-V: halogen atom, C1-C6alkyl, —NHR7, —N(R7)R6 wherein R6 is C1-C6alkyl, C1-C6haloalkyl, —S(O)2R9, —CHO, —C(O)R9, —C(O)OR9, —C(O)SR9, —C(S)OR9 or —C(S)SR9, R7 is hydrogen atom, C1-C6alkyl or C1-C6haloalkyl, R9 is C1-C6alkyl, C1-C6haloalkyl, C3-C8cycloalkyl or C3-C3halocycloalkyl and —N═C(R9)OR8 wherein R8 is C1-C6alkyl, R9 is C1-C6alkyl or C1-C6haloalkyl.
    Y-VI: halogen atom, nitro, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkylthio, C1-C6alkylamino and di(C1-C6alkyl)amino.
  • In the compounds included in the present invention, n indicating the number of substituent Y is an integer of 0 to 4. Among them, n is preferably 0 and 1.
  • In the compounds included in the present invention, the substituent R1 includes for example the following groups.
  • That is, R1-I: C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R16 (wherein R16 is halogen atom, C3-C6cycloalkyl, C3-C6halocycloalkyl, phenyl, phenyl substituted with (Z)p1, D-1 to D-4, D-8 to D-38, D-47 to D-55, E-4 to E-12, E-18, E-19, E-32, E-35, E-43, M-2, M-3, M-5, M-8, M-9 or M-10), C3-C8cycloalkyl and C3-C3halocycloalkyl.
    R1-II: C1-C6alkyl arbitrarily substituted with —OR25 wherein R25 is C1-C6alkyl, C1-C6haloalkyl, C1-C6alkylcarbonyl, C1-C6alkoxycarbonyl, C1-C6alkylaminocarbonyl, di(C1-C6alkyl)aminocarbonyl or C1-C6alkylsulfonyl.
    R1-III: C1-C6alkyl arbitrarily substituted with —N(R26)R25 wherein R25 is C1-C6alkyl, C1-C6haloalkyl, C1-C6alkylcarbonyl, C1-C6alkoxycarbonyl, C1-C6alkylaminocarbonyl, di(C1-C6alkyl)aminocarbonyl or C1-C6alkylsulfonyl, R26 is hydrogen or C1-C6alkyl.
    R1-IV: C1-C6alkyl arbitrarily substituted with —S(O)rR27 wherein R27 is C1-C6alkyl, C1-C6haloalkyl or tri(C1-C4alkyl)silyl C1-C4alkyl, r is an integer of 0 to 2.
    R1-V: C1-C6alkyl arbitrarily substituted with R16 wherein R16 is cyano, —C(O)R28, —C(O)OR28, —C(O)NHR29, —C(O)N(R29)R28, —C(O)N(R29)OR28, —C(S)NHR29, —C(S)N(R29)R28, —SO2NHR29, —SO2N(R29)R28, —C(R31)═NOH, —C(R31)═NOR30, —C(═NR31)OR30 or —C(═NR31)SR36, R28 is C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl C1-C4alkyl, C1-C6alkoxy C1-C4alkyl, C1-C6alkylthio C1-C4alkyl, cyano C1-C6alkyl, phenyl C1-C4alkyl, phenyl C1-C4alkyl substituted with (Z)p1, C3-C6cycloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, phenyl or phenyl substituted with (Z)p1, R29 is hydrogen atom, C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl, R30 is C1-C6alkyl or C3-C6cycloalkyl C1-C4alkyl, R31 is hydrogen atom or C1-C6alkyl, or R31 together with R30 may for 5- or 6-membered ring with the atom bonding them by forming C2-C3alkylene chain.
    R1-VI: C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl, phenyl substituted with (Z)p1, D-8, D-10, D-11, D-13 to D-15, D-17, D-18, D-21 to D-23, D-26 to D-37, D-39, D-40, D-42, D-45, D-47 to D-54, D-56, D-58, E-4, E-5, E-7 and E-9
    R1-VII: —N(R20)R19 wherein R19 is C1-C6haloalkyl, C3-C6cycloalkyl, —C(O)R28, —C(O)OR28, —C(O)NHR29, —C(O)N(R29)R28, —C(S)NHR29, —C(S)N(R29)R28, phenyl, phenyl substituted with (Z)p1, D-3, D-4, D-21, D-47, D-50, D-51, D-53 or D-54, R20 is hydrogen atom, C1-C6alkyl, C1-C4alkoxy C1-C4alkyl, C1-C4alkylthio C1-C4alkyl, cyano C1-C6alkyl, C3-C6alkenyl, C3-C6alkynyl, —CHO, C1-C6alkylcarbonyl, C1-C6alkoxycarbonyl or C1-C6alkylsulfonyl, R28 is C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl C1-C4alkyl, C1-C6alkoxy C1-C4alkyl, C1-C6alkylthio C1-C4alkyl, cyano C1-C6alkyl, phenyl C1-C4alkyl, phenyl C1-C4alkyl substituted with (Z)p1, C3-C6cycloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, phenyl or phenyl substituted with (Z)p1, R29 is hydrogen atom, C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl.
    R1-VIII: C1-C6alkyl, C1-C6haloalkyl, C1-C6alkyl arbitrarily substituted with R16 (wherein R16 is cyano, C3-C6cycloalkyl, C3-C6halocycloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, C1-C6alkylthio, C1-C6haloalkylthio, C1-C6alkylsulfinyl, C1-C6haloalkylsulfinyl, C1-C6alkylsulfonyl, C1-C6haloalkylsulfonyl, C1-C6alkylcarbonyl, —C(O)OR28, —C(O)NHR29, —C(O)N(R29)R28, —C(S)NH2, —C(R31)═NOH, —C(R31)═NOR30, phenyl, phenyl substituted with (Z)p1, D-1 to D-4, D-8 to D-38, D-47 to D-55, E-4 to E-7, E-10, E-11 or E-32, R28 is C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl C1-C4alkyl, C3-C6cycloalkyl, C3-C8alkenyl or C3-C8alkynyl, R29 is hydrogen atom or C1-C6alkyl, R30 is C1-C6alkyl, R31 is hydrogen or C1-C6alkyl), C3-C6cycloalkyl, E-4, E-5, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, —N(R20)R19 (wherein R19 is C1-C6haloalkyl, —C(O)R28, —C(O)OR28, phenyl, phenyl substituted with (Z)p1, D-3, D-4, D-21, D-47, D-50, D-51, D-53 or D-54, R20 is hydrogen atom or C1-C6alkyl, R28 is C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl C1-C4alkyl, C3-C6cycloalkyl, C3-C8alkenyl or C3-C8alkynyl), phenyl substituted with (Z)p1, D-8, D-10, D-13 to D-15, D-18, D-21, D-34, D-35, D-47, D-48, D-50 to D-53 and D-54.
    R1-IX: C1-C6haloalkyl, C1-C6alkyl arbitrarily substituted with R16 (wherein R16 is cyano, C3-C6cycloalkyl, C3-C6halocycloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, C1-C6alkylthio, C1-C6haloalkylthio, C1-C6alkylsulfinyl, C1-C6haloalkylsulfinyl, C1-C6alkylsulfonyl, C1-C6haloalkylsulfonyl, C1-C6alkylcarbonyl, —C(O)OR28, —C(O)NHR29, —C(O)N(R29)R28, —C(S)NH2, —C(R31)═NOH, —C(R31)═NOR30, phenyl substituted with (Z)p1, D-1 to D-4, D-8 to D-38, D-47 to D-55, E-4 to E-7, E-10, E-11 or E-32, R28 is C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl C1-C4alkyl, C3-C6cycloalkyl, C3-C8alkenyl or C3-C8alkynyl, R29 is hydrogen atom or C1-C6alkyl, R30 is C1-C6alkyl, R31 is hydrogen or C1-C6alkyl), C3-C6cycloalkyl, E-4, E-5, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, —N(R20)R19 (wherein R19 is C1-C6haloalkyl, —C(O)R28, —C(O)OR28, phenyl, phenyl substituted with (Z)p1, D-3, D-4, D-21, D-47, D-50, D-51, D-53 or D-54, R20 is hydrogen atom or C1-C6alkyl, R28 is C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl C1-C4alkyl, C3-C6cycloalkyl, C3-C8alkenyl or C3-C8alkynyl), phenyl substituted with (Z)p1, D-8, D-10, D-13 to D-15, D-18, D-21, D-34, D-35, D-47, D-48, D-50 to D-53 and D-54.
    R1-X: C1-C8haloalkyl, C1-C6alkyl arbitrarily substituted with R16 (wherein R16 is C3-C6cycloalkyl, C1-C6alkoxy, C1-C6alkylthio, C1-C6alkylsulfinyl, C1-C6alkylsulfonyl, —C(O)NH2, —C(O)NHR28, —C(S)NH2, —C(R31)═NOH, —C(R31)═NOR30, D-1 to D-4, D-8 to D-38, D-47 to D-54, E-4 to E-7, E-10, E-11 or E-32, R28 is C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl, C3-C8alkenyl or C3-C8alkynyl, R30 is C1-C6alkyl, R31 is hydrogen or C1-C6alkyl), C3-C6cycloalkyl, E-4, E-5, C3-C8alkenyl, C3-C8haloalkenyl, C3-C8alkynyl, —N(R20)R19 (wherein R19 is C1-C6haloalkyl, —C(O)R28, —C(O)OR28, phenyl, D-3, D-4, D-21, D-47, D-50, D-51, D-53 or D-54, R20 is hydrogen atom or C1-C6alkyl, R28 is C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl C1-C4alkyl, C3-C6cycloalkyl, C3-C8alkenyl or C3-C8alkynyl), D-8, D-10, D-13 to D-15, D-18, D-21, D-34, D-35, D-47, D-48, D-50 to D-53 and D-54.
    R1-XI: C1-C6alkyl and phenyl C1-C6alkyl.
    R1-XII: C1-C8alkyl, C1-C8alkyl arbitrarily substituted with R16 (wherein R16 is halogen atom, C3-C6cycloalkyl, C3-C6halocycloalkyl, phenyl, phenyl substituted with (Z)p1, D-1 to D-4, D-8 to D-42, D-47 to D-55, E-4 to E-12, E-14, E-16 to E-19, E-21 to E-23, E-26 to E-35, E-40 to E-45, E-48, M-2, M-3, M-5, M-8 to M-10, M-14, M-15 or M-16), C3-C8cycloalkyl and C3-C8halocycloalkyl.
    R1-XIII: C1-C8alkyl arbitrarily substituted with —OR25 wherein R25 is hydrogen atom, C1-C6alkyl, C1-C6haloalkyl, —C(O)R33, —C(O)OR33, —C(O)NHR34, —C(O)N(R34)R33, —C(S)NHR34, —C(S)N(R34)R33, —S(O)2R33, —S(O)2N(R34)R33, di(C1-C6alkyl)thiophosphoryl, phenyl or phenyl substituted with (Z)p1, R33 is C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl, C3-C6halocycloalkyl, phenyl C1-C4alkyl, phenyl C1-C4alkyl substituted with (Z)p1, C3-C6alkenyl, C3-C6alkynyl, phenyl or phenyl substituted with (Z)p1, R34 is hydrogen atom or C1-C6alkyl.
    R1-XIV: C1-C8alkyl arbitrarily substituted with —N(R26)R25 wherein R25 is C1-C6alkyl, C1-C6haloalkyl, —C(O)R33, —C(O)OR33, —C(O)SR33, —C(O)NHR34, —C(O)N(R34)R33, —C(S)R33, —C(S)OR33, —C(S)SR33, —C(S)NHR34, —C(S)N(R34)R33, —S(O)2R33 or —S(O)2N(R34)R33, R26 is hydrogen atom or C1-C6alkyl, or R26 together with R25 may form 4- to 6-membered ring with the nitrogen atom bonding them by forming C3-C5alkylene chain, in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and may be substituted with C1-C6alkyl, oxo or thioxo, R33 is C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl, C3-C6halocycloalkyl, phenyl C1-C4alkyl, phenyl C1-C4alkyl substituted with (Z)p1, C3-C6alkenyl, C3-C6alkynyl, phenyl or phenyl substituted with (Z)p1, R34 is hydrogen atom or C1-C6alkyl.
    R1-XV: C1-C8alkyl arbitrarily substituted with —S(O)rR27 wherein R27 is C1-C6alkyl, C1-C6haloalkyl, tri(C1-C4alkyl)silyl C1-C4alkyl, C1-C6alkylthio, —C(O)NHR34, —C(O)N(R34)R33, —C(S)NHR34, —C(S)N(R34)R33, phenyl, phenyl substituted with (Z)p1, D-47 or D-50, R33 is C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl, C3-C6halocycloalkyl, phenyl C1-C4alkyl, phenyl C1-C4alkyl substituted with (Z)p1, C3-C6alkenyl, C3-C6alkynyl, phenyl or phenyl substituted with (Z)p1, R34 is hydrogen atom or C1-C6alkyl, r is an integer of 0 to 2.
    R1-XVI: C1-C8alkyl arbitrarily substituted with R16 wherein R16 is cyano, —SO2NHR29, —SO2N(R29)R28, —CHO, —C(O)R28, —C(O)OR28, —C(O)NHR29, —C(O)N(R29)R28, —C(S)NHR29, —C(S)N(R29)R28, —C(R31)═NOH, —C(R31)═NOR30, —C(═NR31)OR30, —C(═NR31)SR30, —C(═NR31)N(R30)R29, —C(═NOR31)NHR29 or —C(═NOR31)N(R30)R29, R28 is C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R32, C3-C6cycloalkyl, C3-C6halocycloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkenyl, phenyl or phenyl substituted with (Z)p1, R29 is hydrogen atom, C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl, or R29 together with R28 may form 3- to 6-membered ring with the nitrogen atom bonding them by forming C2-C5alkylene chain, in this case, the alkylene chain may contain one oxygen atom or sulfur atom, R30 is C1-C6alkyl, C3-C6cycloalkyl C1-C4alkyl, phenyl C1-C4alkyl, phenyl C1-C4alkyl substituted with (Z)p1, C3-C8alkenyl or C3-C8alkynyl, R31 is hydrogen atom or C1-C6alkyl, or R31 together with R30 may form 5- or 6-membered ring with the atom bonding them by forming C2-C3alkylene chain, in this case, the alkylene chain may be arbitrarily substituted with C1-C6alkyl, R32 is halogen atom, cyano, C3-C6cycloalkyl, C3-C6halocycloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylthio, C1-C4haloalkylthio, C1-C4alkoxycarbonyl, —C(O)NH2, C1-C4alkylaminocarbonyl, di(C1-C4alkyl)aminocarbonyl, phenyl or phenyl substituted with (Z)p1.
    R1-XVII: C3-C8alkenyl, C3-C8haloalkenyl, C3-C8alkynyl, C3-C8haloalkynyl, phenyl substituted with (Z)p1, D-8 to D-18, D-21 to D-24, D-26 to D-40, D-42, D-45 to D-58, E-4, E-5, E-7, E-9, E-23 to E-25, E-27, E-28, E-30, E-31 and E-34.
    R1-XVIII: —N(R20)R19 wherein R19 is C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl C1-C6alkyl, phenyl C1-C6alkyl, phenyl C1-C6alkyl substituted with (Z)p1, C3-C6cycloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, —C(O)R28, —C(O)OR28, —C(O)NHR29, —C(O)N(R29)R28, —C(S)NHR29, —C(S)N(R29)R28, C1-C6alkylsulfonyl, C1-C6haloalkylsulfonyl, phenylsulfonyl, phenylsulfonyl substituted with (Z)p1, phenyl, phenyl substituted with (Z)p1, D-1 to D-4, D-18, D-21, D-25, D-30 to D-35, D-47 to D-55 or D-56, R20 is hydrogen atom, C1-C6alkyl, C1-C4alkoxy C1-C4alkyl, C1-C4alkylthio C1-C4alkyl, cyano C1-C6alkyl, C3-C6alkenyl, C3-C6alkynyl, —CHO, C1-C6alkylcarbonyl, C1-C6haloalkylcarbonyl, C1-C6alkoxycarbonyl, C1-C6haloalkoxycarbonyl or C1-C6alkylsulfonyl, R28 is C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R32, C3-C6cycloalkyl, C3-C6halocycloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl, phenyl or phenyl substituted with (Z)p1, R29 is hydrogen atom, C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl, R29 together with R28 may form 3- to 6-membered ring with the nitrogen atom bonding them by forming C2-C5alkylene chain, in this case, the alkylene chain may contain one oxygen atom or sulfur atom, R32 is hydrogen atom, cyano, C3-C6cycloalkyl, C3-C6halocycloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylthio, C1-C4haloalkylthio, C1-C4alkoxycarbonyl, —C(O)NH2, C1-C4alkylaminocarbonyl, di(C1-C4alkyl)aminocarbonyl, phenyl or phenyl substituted with (Z)p1.
  • In the compounds included in the present invention, the substituent R2 includes for example the following groups.
  • That is, R2-I: hydrogen atom.
  • R2-II: C1-C6alkyl, C1-C6haloalkyl and C3-C6cycloalkyl.
  • R2-III: C1-C4alkoxy C1-C4alkyl, C1-C4alkylthio C1-C4alkyl and cyano C1-C6alkyl.
    R2-IV: C3-C6alkenyl and C3-C6alkynyl.
    R2-V: —OH, C1-C6alkoxy, C1-C6alkylcarbonyloxy, C1-C6alkoxycarbonyloxy and C1-C6alkylsulfonyloxy.
    R2-VI: C1-C6haloalkylthio, phenylthio, phenylthio substituted with (Z)p1 and —SN(R18)R17 wherein R17 is C1-C6alkyl, C1-C6alkoxycarbonyl C1-C4alkyl or C1-C6alkoxycarbony, R18 is C1-C6alkyl or benzyl.
    R2-VII: —NHR20 (wherein R20 is hydrogen atom, C1-C6alkyl, —CHO, C1-C6alkylcarbonyl, C1-C6alkoxycarbonyl or C1-C6alkylsulfonyl), —N═CHR19b and —N═C(R19b)R19a wherein R19a is C1-C6alkyl, R19b is hydrogen atom or C1-C6alkyl.
    R2-VIII: —C(O)R9, —C(O)OR9, —C(O)SR9, —C(S)OR9, —C(S)SR9 (wherein R9 is C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl C1-C4alkyl, C1-C6alkoxy C1-C4alkyl, C1-C6alkylthio C1-C4alkyl, cyano C1-C6alkyl, phenyl C1-C4alkyl, C3-C8cycloalkyl, C3-C8halocycloalkyl, C3-C6alkenyl or C3-C6alkynyl) and C1-C6alkylsulfonyl.
    R2-IX: 3- to 7-membered ring that R2 forms together with R1 is aziridine, azetidine, pyrrolidine, oxazolidine, thiazoridine, piperidine, morpholine, thiomorpholine and homopiperidine.
    R2-X: hydrogen atom, C1-C6alkyl, C1-C4alkoxy C1-C4alkyl, C1-C4alkylthio C1-C4alkyl, cyano C1-C6alkyl, C3-C6cycloalkyl, C3-C6alkenyl, C3-C6alkynyl, —OH, C1-C6alkylcarbonyloxy, C1-C6alkylsulfonyloxy, —NH2, —C(O)R9, —C(O)OR9, —C(O)SR9, —C(S)OR9 and —C(S)SR9 wherein R9 is C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl C1-C4alkyl, C1-C6alkoxy C1-C4alkyl, C1-C6alkylthio C1-C4alkyl, cyano C1-C6alkyl, C3-C8cycloalkyl, C3-C6alkenyl or C3-C6alkynyl.
    R2—XI: hydrogen atom, C1-C6alkyl, C1-C4alkoxy C1-C4alkyl, cyano C1-C6alkyl, C3-C6alkynyl, —C(O)R9 and —C(O)OR9 wherein R9 is C1-C6alkyl, C1-C6alkoxy C1-C4alkyl, C1-C6alkylthio C1-C4alkyl, C3-C8cycloalkyl, C3-C6alkenyl or C3-C6alkynyl.
  • In the compounds included in the present invention, the substituent R3 includes for example the following groups.
  • That is, R3-I: C1-C6haloalkyl and C3-C8halocycloalkyl.
    R3-II: C1-C6alkyl, C3-C8cycloalkyl, E-4 to E-7, E-23 to E-27 and E-28.
    R3-III: C1-C4alkoxy C1-C4haloalkyl, C1-C4haloalkoxy C1-C4haloalkyl, C1-C4alkylthio C1-C4haloalkyl, C1-C4alkylsulfinyl C1-C4haloalkyl, C1-C4alkylsulfonyl C1-C4haloalkyl, C1-C4haloalkylthio C1-C4haloalkyl, C1-C4haloalkylsulfinyl C1-C4haloalkyl, C1-C4haloalkylsulfonyl C1-C4haloalkyl and cyano C1-C6haloalkyl.
    R3-IV: C3-C6cycloalkyl C1-C4alkyl, C3-C6halocycloalkyl C1-C4alkyl, C1-C4alkoxy C1-C4alkyl, C1-C4haloalkoxy C1-C4alkyl, C1-C4alkylthio C1-C4alkyl, C1-C4alkylsulfinyl C1-C4alkyl, C1-C4alkylsulfonyl C1-C4alkyl, C1-C4haloalkylthio C1-C4alkyl, C1-C4haloalkylsulfinyl C1-C4alkyl, C1-C4haloalkylsulfonyl C1-C4alkyl and cyano C1-C6alkyl.
    R3—V: C1-C6haloalkyl, C1-C4alkoxy C1-C4haloalkyl, C1-C4haloalkoxy C1-C4haloalkyl, C1-C4alkylthio C1-C4haloalkyl, C1-C4haloalkylthio C1-C4haloalkyl, cyano C1-C6haloalkyl and C3-C8halocycloalkyl.
    R3-VI: C1-C6haloalkyl.
    R3-VII: C1-C6alkyl arbitrarily substituted with two or more arbitrary halogen atoms.
  • Each group showing the scope of each substituent in the compounds included in the present invention can be arbitrarily combined one another, and all combination thereof falls within the scope of the present invention. Examples of the combination of the scope of X, Y and R1 include for example the combination showin in Table 1. In the meantime, the combination of Table 1 is for illustrative purposes, and the present invention is not limited thereto.
  • TABLE 1
    X Y R1
    X-I Y-I R1-I
    X-I Y-I R1-II
    X-I Y-I R1-III
    X-I Y-I R1-IV
    X-I Y-I R1-V
    X-I Y-I R1-VI
    X-I Y-I R1-VII
    X-I Y-I R1-VIII
    X-I Y-I R1-IX
    X-I Y-I R1-X
    X-I Y-I R1-XI
    X-I Y-II R1-I
    X-I Y-II R1-II
    X-I Y-II R1-III
    X-I Y-II R1-IV
    X-I Y-II R1-V
    X-I Y-II R1-VI
    X-I Y-II R1-VII
    X-I Y-II R1-VIII
    X-I Y-II R1-IX
    X-I Y-II R1-X
    X-I Y-II R1-XI
    X-I Y-III R1 -I
    X-I Y-III R1-VII
    X-I Y-III R1 -VIII
    X-I Y-III R1-IX
    X-I Y-III R1-X
    X-I Y-IV R1-I
    X-I Y-IV R1-II
    X-I Y-IV R1-III
    X-I Y-IV R1-IV
    X-I Y-IV R1-V
    X-I Y-IV R1-VI
    X-I Y-IV R1-VII
    X-I Y-IV R1-VIII
    X-I Y-IV R1-IX
    X-I Y-IV R1-X
    X-I Y-IV R1-XI
    X-I Y-V R1-I
    X-I Y-V R1-II
    X-I Y-V R1-III
    X-I Y-V R1-IV
    X-I Y-V R1-V
    X-I Y-V R1-VI
    X-I Y-V R1-VII
    X-I Y-V R1-VIII
    X-I Y-V R1-IX
    X-I Y-V R1-X
    X-I Y-V R1-XI
    X-I Y-VI R1-I
    X-I Y-VI R1-II
    X-I Y-VI R1-III
    X-I Y-VI R1-IV
    X-I Y-VI R1-V
    X-I Y-VI R1-VI
    X-I Y-VI R1-VII
    X-I Y-VI R1-VIII
    X-I Y-VI R1-IX
    X-I Y-VI R1-X
    X-I Y-VI R1-XI
    X-II Y-I R1-I
    X-II Y-I R1-II
    X-II Y-I R1-III
    X-II Y-I R1-IV
    X-II Y-I R1-V
    X-II Y-I R1-VI
    X-II Y-I R1-VII
    X-II Y-I R1-VIII
    X-II Y-I R1-IX
    X-II Y-I R1-X
    X-II Y-II R1-X
    X-II Y-III R1-X
    X-II Y-IV R1-X
    X-II Y-V R1-X
    X-II Y-VI R1-I
    X-II Y-VI R1-II
    X-II Y-VI R1-III
    X-II Y-VI R1-IV
    X-II Y-VI R1-V
    X-II Y-VI R1-VI
    X-II Y-VI R1-VII
    X-II Y-VI R1-VIII
    X-II Y-VI R1-IX
    X-II Y-VI R1-X
    X-III Y-I R1-I
    X-III Y-I R1-II
    X-III Y-I R1-III
    X-III Y-I R1-IV
    X-III Y-I R1-V
    X-III Y-I R1-VI
    X-III Y-I R1-VII
    X-III Y-I R1-VIII
    X-III Y-I R1-IX
    X-III Y-I R1-X
    X-III Y-I R1-XI
    X-III Y-II R1-X
    X-III Y-III R1-X
    X-III Y-IV R1-X
    X-III Y-V R1-X
    X-III Y-VI R1-I
    X-I Y-I R1-XII
    X-I Y-I R1-XIII
    X-I Y-I R1-XIV
    X-I Y-I R1-XV
    X-I Y-I R1-XVI
    X-I Y-I R1-XVII
    X-I Y-I R1-XVIII
    X-III Y-I R1-XII
    X-III Y-I R1-XIII
    X-III Y-I R1-XIV
    X-III Y-I R1-XV
    X-III Y-I R1-XVI
    X-III Y-I R1-XVII
    X-III Y-I R1-XVIII
    X-III Y-VI R1-II
    X-III Y-VI R1-III
    X-III Y-VI R1-IV
    X-III Y-VI R1-V
    X-III Y-VI R1-VI
    X-III Y-VI R1-VII
    X-III Y-VI R1-VIII
    X-III Y-VI R1-IX
    X-III Y-VI R1-X
    X-III Y-VI R1-XI
    X-IV Y-I R1-I
    X-IV Y-I R1-II
    X-IV Y-I R1-III
    X-IV Y-I R1-IV
    X-IV Y-I R1-V
    X-IV Y-I R1-VI
    X-IV Y-I R1-VII
    X-IV Y-I R1-VIII
    X-IV Y-I R1-IX
    X-IV Y-I R1-X
    X-IV Y-I R1-XI
    X-IV Y-II R1-X
    X-IV Y-III R1-X
    X-IV Y-IV R1-X
    X-IV Y-V R1-X
    X-IV Y-VI R1-I
    X-IV Y-VI R1-II
    X-IV Y-VI R1-III
    X-IV Y-VI R1-IV
    X-IV Y-VI R1-V
    X-IV Y-VI R1-VI
    X-IV Y-VI R1-VII
    X-IV Y-VI R1-VIII
    X-IV Y-VI R1-IX
    X-IV Y-VI R1-X
    X-IV Y-VI R1-XI
    X-V Y-I R1-I
    X-V Y-I R1-VII
    X-V Y-I R1-IX
    X-V Y-I R1-X
    X-V Y-II R1-X
    X-V Y-III R1-X
    X-V Y-IV R1-X
    X-V Y-V R1-X
    X-V Y-VI R1-I
    X-V Y-VI R1-VII
    X-V Y-VI R1-IX
    X-V Y-VI R1-X
    X-VI Y-I R1-I
    X-VI Y-I R1-II
    X-VI Y-I R1-III
    X-VI Y-I R1-IV
    X-VI Y-I R1-V
    X-VI Y-I R1-VI
    X-VI Y-I R1-VII
    X-VI Y-I R1-VIII
    X-VI Y-I R1-IX
    X-VI Y-I R1-X
    X-VI Y-II R1-X
    X-VI Y-III R1-X
    X-VI Y-IV R1-X
    X-VI Y-V R1-X
    X-VI Y-VI R1-I
    X-VI Y-VI R1-II
    X-VI Y-VI R1-III
    X-VI Y-VI R1-IV
    X-VI Y-VI R1-V
    X-VI Y-VI R1-VI
    X-VI Y-VI R1-VII
    X-VI Y-VI R1-VIII
    X-VI Y-VI R1-IX
    X-VI Y-VI R1-X
    X-VII Y-I R1-I
    X-VII Y-I R1-II
    X-VII Y-I R1-III
    X-VII Y-I R1-IV
    X-VII Y-I R1-V
    X-VII Y-I R1-VI
    X-VII Y-I R1-VII
    X-VII Y-I R1-VIII
    X-VII Y-I R1-IX
    X-VII Y-I R1-X
    X-VII Y-II R1-X
    X-VII Y-III R1-X
    X-VII Y-IV R1-X
    X-VII Y-V R1-X
    X-VII Y-VI R1-I
    X-VII Y-VI R1-II
    X-VII Y-VI R1-III
    X-VII Y-VI R1-IV
    X-VII Y-VI R1-V
    X-VII Y-VI R1-VI
    X-VII Y-VI R1-VII
    X-VII Y-VI R1-VIII
    X-VII Y-VI R1-IX
    X-VII Y-VI R1-X
    X-VIII Y-I R1-X
    X-VIII Y-VI R1-X
    X-IX Y-I R1-X
    X-IX Y-VI R1-X
    X-I Y-VI R1-XII
    X-I Y-VI R1-XIII
    X-I Y-VI R1-XIV
    X-I Y-VI R1-XV
    X-I Y-VI R1-XVI
    X-I Y-VI R1-XVII
    X-I Y-VI R1-XVIII
    X-III Y-VI R1-XII
    X-III Y-VI R1-XIII
    X-III Y-VI R1-XIV
    X-III Y-VI R1-XV
    X-III Y-VI R1-XVI
    X-III Y-VI R1-XVII
    X-III Y-VI R1-XVIII
  • The compounds of the present invention can be produced for example according to the methods mentioned below.
    • Production Method A
  • Figure US20150105398A1-20150416-C00029
  • The compound of formula (1-1) wherein A1, A2, A3, G, X, Y, R1, R2, R3, m and n are as defined above that is the compound of formula (1) wherein W is oxygen atom can be obtained by reacting the compound of formula (5) wherein A1, A2, A3, G, X, Y, R3, m and n are as defined above with the compound of formula (6) wherein R1 and R2 are as defined above by use of a condensation agent, optionally by using a solvent inactive for the reaction, optionally in the presence of a base.
  • The reaction substrates can be used in an amount of 1 to 100 equivalents of the compound of formula (6) based on 1 equivalent of the compound of formula (5).
  • The condensation agent is not specifically limited if it is a compound used for ordinary amide synthesis, but it is for example Mukaiyama agent (2-chloro-N-methylpyridinium iodide), DCC (1,3-dicyclohexyl carbodiimide), WSC (1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride), CDI (carbonyl diimidazole), dimethylpropynyl sulfonium bromide, propagyl triphenyl phosphonium bromide, DEPC (diethyl phosphorocyanidate) or the like, and can be used in an amount of 1 to 4 equivalents based on the compound of formula (5).
  • In case where a solvent is used, the solvent is not specifically limited if it dose not inhibit the progress of the reaction, but it includes for example aromatic hydrocarbons such as benzene, toluene, xylene or the like, aliphatic hydrocarbons such as hexane, heptane or the like, alicyclic hydrocarbons such as cyclohexane or the like, aromatic halogenated hydrocarbons such as chlorobenzene, dichlorobenzene or the like, aliphatic halogenated hydrocarbons such as dichloro methane, chloroform, carbon tetrachloride, 1,2-dichloroethane, 1,1,1-trichloroethane, trichloroethylene, tetrachloroethylene or the like, ethers such as diethyl ether, 1,2-dimethoxyethane, tetrahydrofuran, 1,4-dioxane or the like, esters such as ethyl acetate, ethyl propionate or the like, amides such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrolidone or the like, amines such as triethyl amine, tributyl amine, N,N-dimethyl aniline or the like, pyridines such as pyridine, picoline or the like, acetonitrile and dimethyl sulfoxide, and the like. These solvents may be used alone or in a mixture of two or more.
  • The addition of a base is not necessarily required. However, when the base is used, alkali metal hydroxides such as sodium hydroxide, potassium hydroxide or the like, alkali metal carbonates such as sodium carbonate, potassium carbonate or the like, alkali metal bicarbonates such as sodium hydrogen carbonate, potassium hydrogen carbonate or the like, organic bases such as triethyamine, tributylamine, N,N-dimethylaniline, pyridine, 4-(dimethylamino)pyridine, imidazole, 1,8-diazabicyclo[5.4.0]-7-undecene, and the like can be used in an amount of 1 to 4 equivalents based on the compound of formula (5).
  • The reaction temperature may be an arbitrary temperature ranging from −60° C. to the reflux temperature of a reaction mixture, and the reaction time may be an arbitrary time ranging from 5 minutes to 100 hours although it varies depending on the concentration of the reaction substrates or the reaction temperature.
  • Generally, it is preferable to carry out the reaction by using 1 to 20 equivalents of the compound of formula (6) and 1 to 4 equivalent of the condensation agent such as WSC (1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride), CDI (carbonyl diimidazole) or the like based on 1 equivalent of the compound of formula (5), optionally in the presence of 1 to 4 equivalents of a base such as potassium carbonate, triethylamine, pyridine, 4-(dimethylamino)pyridine or the like, without solvent or in a solvent such as dichloromethane, chloroform, diethyl ether, tetrahydrofurane, 1,4-dioxane or the like, at a temperature ranging from 0° C. to the reflux temperature of these solvents for 10 minutes to 24 hours.
  • In addition, the compound of formula (1-1) according to the present invention can be also synthesized by reacting the compound of formula (7) wherein A1, A2, A3, G, X, Y, R3, m and n are as defined above, J1 is chlorine atom, bromine atom, C1-C4alkylcarbonyloxy (for example pivaloyloxy), C1-C4alkoxycarbonyloxy (for example isobutyloxycarbonyloxy) or azolyl (for example imidazol-1-yl) that can be synthesized according to a known method disclosed in documents from the compound of formula (5), for example a method by reacting with a chlorinating agent such as thionyl chloride, phosphorus pentachloride or oxalyl chloride, a method by reacting with a organic acid halide such as pivaloyl chloride or isobutyl chlorformate, etc. optionally in the presence of a base, or a method by reacting with carbonyl diimidazole or sulfonyl diimidazole, etc., with the compound of formula (6), optionally by using a solvent inactive for the reaction, optionally in the presence of a base.
  • The reaction substrates can be used in an amount of 1 to 50 equivalents of the compound of formula (6) based on 1 equivalent of the compound of formula (7).
  • In case where a solvent is used, the solvent is not specifically limited if it dose not inhibit the progress of the reaction, but it includes for example aromatic hydrocarbons such as benzene, toluene, xylene or the like, aliphatic hydrocarbons such as hexane, heptane or the like, alicyclic hydrocarbons such as cyclohexane or the like, aromatic halogenated hydrocarbons such as chlorobenzene, dichlorobenzene or the like, aliphatic halogenated hydrocarbons such as dichloro methane, chloroform, carbon tetrachloride, 1,2-dichloroethane, 1,1,1-trichloroethane, trichloroethylene, tetrachloroethylene or the like, ethers such as diethyl ether, 1,2-dimethoxyethane, tetrahydrofuran, 1,4-dioxane or the like, esters such as ethyl acetate, ethyl propionate or the like, amides such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrolidone or the like, amines such as triethyl amine, tributyl amine, N,N-dimethyl aniline or the like, pyridines such as pyridine, picoline or the like, acetonitrile and water, and the like. These solvents may be used alone or in a mixture of two or more.
  • The addition of a base is not necessarily required. However, when the base is used, alkali metal hydroxides such as sodium hydroxide, potassium hydroxide or the like, alkali metal carbonates such as sodium carbonate, potassium carbonate or the like, alkali metal bicarbonates such as sodium hydrogen carbonate, potassium hydrogen carbonate or the like, organic bases such as triethyamine, tributylamine, N,N-dimethylaniline, pyridine, 4-(dimethylamino)pyridine, imidazole, 1,8-diazabicyclo[5.4.0]-7-undecene, and the like can be used in an amount of 1 to 4 equivalents based on the compound of formula (7).
  • The reaction temperature may be an arbitrary temperature ranging from −60° C. to the reflux temperature of a reaction mixture, and the reaction time may be an arbitrary time ranging from 5 minutes to 100 hours although it varies depending on the concentration of the reaction substrates or the reaction temperature.
  • Generally, it is preferable to carry out the reaction by using 1 to 10 equivalents of the compound of formula (6) based on 1 equivalent of the compound of formula (7), optionally in the presence of 1 to 2 equivalents of a base such as potassium carbonate, triethylamine, pyridine, 4-(dimethylamino)pyridine or the like, without solvent or in a solvent such as dichloromethane, chloroform, diethyl ether, tetrahydrofurane, 1,4-dioxane, ethyl acetate, acetonitrile or the like, at a temperature ranging from 0° C. to the reflux temperature of these solvents for 10 minutes to 24 hours.
    • Production Method B
  • Figure US20150105398A1-20150416-C00030
  • Hydroxamic chloride of formula (9) wherein A1, A2, A3, W, Y, R1, R2 and n are as defined above, J2 means halogen atom such as chlorine atom and bromine atom can be obtained by halogenating the compound of formula (8) wherein A1, A2, A3, W, Y, R1, R2 and n are as defined above using a halogenating reagent optionally by using a solvent inactive for the reaction, optionally in the presence of a base.
  • Halogenating agents include for example N-halosuccinimides such as N-chlorosuccinimide, N-bromosuccinimide or the like, hypohalogenous acid alkali metal salts such as sodium hypochlorite or the like, hypohalogenous acid esters such as hypochlorous acid-t-butyl ester or the like, simple substance halogens such as chlorine gas or the like, and it can be used in an amount of 1 to 10 equivalents based on the compound of formula (8).
  • In case where a solvent is used, the solvent is not specifically limited if it dose not inhibit the progress of the reaction, but it includes for example aromatic hydrocarbons such as benzene, toluene, xylene or the like, aliphatic hydrocarbons such as hexane, heptane or the like, alicyclic hydrocarbons such as cyclohexane or the like, aromatic halogenated hydrocarbons such as chlorobenzene, dichlorobenzene or the like, aliphatic halogenated hydrocarbons such as dichloro methane, chloroform, carbon tetrachloride, 1,2-dichloroethane, 1,1,1-trichloroethane, trichloroethylene, tetrachloroethylene or the like, ethers such as diethyl ether, 1,2-dimethoxyethane, tetrahydrofuran, 1,4-dioxane or the like, esters such as ethyl acetate, ethyl propionate or the like, amides such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrolidone or the like, alcohols such as methanol, ethanol, ethylene glycol or the like, carboxylic acids such as acetic acid, propionic acid or the like, acetonitrile and water, and the like. These solvents may be used alone or in a mixture of two or more.
  • The reaction temperature may be an arbitrary temperature ranging from −60° C. to the reflux temperature of a reaction mixture, and the reaction time may be an arbitrary time ranging from 5 minutes to 24 hours although it varies depending on the concentration of the reaction substrates or the reaction temperature.
  • The compounds of formula (1) wherein A1, A2, A3, G, W, X, Y, R1, R2, R3, m and n are as defined above according to the present invention can be obtained by reacting the compound of formula (9) with the compound of formula (10) wherein G, X, R3 and m are as defined above in the presence of a base optionally by use of a solvent inactive for the reaction.
  • The reaction substrates can be used in an amount of 1 to 5 equivalents of the compound of formula (10) based on 1 equivalent of the compound of formula (9).
  • The used base includes for example alkali metal hydroxides such as sodium hydroxide, potassium hydroxide or the like, alkali metal carbonates such as sodium carbonate, potassium carbonate or the like, alkali metal bicarbonates such as sodium hydrogen carbonate, potassium hydrogen carbonate or the like, organic bases such as triethyamine, tributylamine, N,N-dimethylaniline, pyridine, 4-(dimethylamino)pyridine, imidazole, 1,8-diazabicyclo[5.4.0]-7-undecene, and the like can be used in an amount of 1 to 5 equivalents based on the compound of formula (9).
  • In case where a solvent is used, the solvent is not specifically limited if it dose not inhibit the progress of the reaction, but it includes for example aromatic hydrocarbons such as benzene, toluene, xylene or the like, aliphatic hydrocarbons such as hexane, heptane or the like, alicyclic hydrocarbons such as cyclohexane or the like, aromatic halogenated hydrocarbons such as chlorobenzene, dichlorobenzene or the like, aliphatic halogenated hydrocarbons such as dichloro methane, chloroform, carbon tetrachloride, 1,2-dichloroethane, 1,1,1-trichloroethane, trichloroethylene, tetrachloroethylene or the like, ethers such as diethyl ether, 1,2-dimethoxyethane, tetrahydrofuran, 1,4-dioxane or the like, esters such as ethyl acetate, ethyl propionate or the like, amides such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrolidone or the like, and acetonitrile, and the like. These solvents may be used alone or in a mixture of two or more.
  • The reaction temperature may be an arbitrary temperature ranging from −60° C. to the reflux temperature of a reaction mixture, and the reaction time may be an arbitrary time ranging from 5 minutes to 100 hours although it varies depending on the concentration of the reaction substrates or the reaction temperature.
  • Generally, the compound of formula (9) can be obtained for example by carrying out the reaction by using 1 to 2 equivalents of a halogenating agent such as N-chlorosuccinimide, sodium hypochlorite aqueous solution, hypochlorous acid-t-butyl ester, chlorine gas or the like based on 1 equivalent of the compound of formula (8) in a solvent such as dichloromethane, chloroform, 1,2-dimethoxyethane, tetrahydrofurane, 1,4-dioxane, N,N-dimethylformamide or the like, at a temperature ranging from 0° C. to the reflux temperature of these solvents for 10 minutes to 2 hours. Then, preferably without the isolation of the compound of formula (9), 1 to 2 equivalents of the compound of formula (10) and 1 to 2 equivalents of a base such as sodium carbonate, sodium hydrogen carbonate, triethyl amine or the like are added, and the reaction is carried out at a temperature ranging from 0° C. to the reflux temperature of these solvents for 10 minutes to 24 hours.
    • Production Method C
  • Figure US20150105398A1-20150416-C00031
  • The compound of formula (1-1) wherein A1, A2, A3, G, X, Y, R1, R3, m and n are as defined above and R2 has the same meaning defined above excluding hydrogen atom according to the present invention that is the compound of formula (1) wherein W is oxygen atom can be obtained by reacting the compound of formula (1-2) wherein A1, A2, A3, G, X, Y, R1, R3, m and n are as defined above that is the compound of formula (1) wherein W is oxygen atom and R2 is hydrogen atom with the compound of formula (11) wherein R2 has the same meaning defined above excluding hydrogen atom, J3 is a good leaving group such as chlorine atom, bromine atom, iodine atom, C1-C4alkylcarbonyloxy (for example pivaloyloxy), C1-C4alkylsulfonate (for example methane sulfonyloxy), C1-C4haloalkylsulfonate (for example trifluoromethane sulfonyloxy), arylsulfonate (for example benzene sulfonyloxy, p-toluene sulfonyloxy) or azolyl (for example imidazol-1-yl), optionally in the presence of a base, optionally by using a solvent inactive for the reaction.
  • The reaction substrates can be used in an amount of 1 to 50 equivalents of the compound of formula (11) based on 1 equivalent of the compound of formula (1-2).
  • In case where a solvent is used, the solvent is not specifically limited if it dose not inhibit the progress of the reaction, but it includes for example aromatic hydrocarbons such as benzene, toluene, xylene or the like, aliphatic hydrocarbons such as hexane, heptane or the like, alicyclic hydrocarbons such as cyclohexane or the like, aromatic halogenated hydrocarbons such as chlorobenzene, dichlorobenzene or the like, aliphatic halogenated hydrocarbons such as dichloro methane, chloroform, carbon tetrachloride, 1,2-dichloroethane, 1,1,1-trichloroethane, trichloroethylene, tetrachloroethylene or the like, ethers such as diethyl ether, 1,2-dimethoxyethane, tetrahydrofuran, 1,4-dioxane or the like, esters such as ethyl acetate, ethyl propionate or the like, amides such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrolidone or the like, amines such as triethyl amine, tributyl amine, N,N-dimethyl aniline or the like, pyridines such as pyridine, picoline or the like, alcoholes such as methanol, ethanol, ethylene glycol or the like, acetonitrile, dimethylsulfoxide, sulfolane, 1,3-dimethyl-2-imidazolidinone and water, and the like. These solvents may be used alone or in a mixture of two or more.
  • When the base is used, alkali metal hydride such as sodium hydride, potassium hydride or the like, alkali metal hydroxides such as sodium hydroxide, potassium hydroxide or the like, alkali metal alkoxides such as sodium ethoxide, potassium t-butoxide or the like, alkali metal amides such as lithium diisopropylamide, lithium hexamethyl disilazane, sodium amide or the like, organic metal compounds such as t-butyl lithium or the like, alkali metal carbonates such as sodium carbonate, potassium carbonate, sodium hydrogen carbonate or the like, organic bases such as triethyamine, tributylamine, N,N-dimethylaniline, pyridine, 4-(dimethylamino)pyridine, imidazole, 1,8-diazabicyclo[5.4.0]-7-undecene, and the like can be used in an amount of 1 to 4 equivalents based on the compound of formula (1-2).
  • The reaction temperature may be an arbitrary temperature ranging from −60° C. to the reflux temperature of a reaction mixture, and the reaction time may be an arbitrary time ranging from 5 minutes to 100 hours although it varies depending on the concentration of the reaction substrates or the reaction temperature.
  • Generally, it is preferable to carry out the reaction by using 1 to 10 equivalents of the compound of formula (11) based on 1 equivalent of the compound of formula (1-2), in a polar solvent such as tetrahydrofurane, 1,4-dioxane, acetonitrile, N,N-dimethylformamide or the like, optionally in the presence of 1 to 3 equivalents of a base such as sodium hydride, potassium t-butoxide, potassium hydroxide, potassium carbonate, triethylamine, pyridine or the like, based on 1 equivalent of the compound of formula (1-2), at a temperature ranging from 0 to 90° C. for 10 minutes to 24 hours.
    • Production Method D
  • Figure US20150105398A1-20150416-C00032
  • The compound of formula (1-3) wherein A1, A2, A3, G, X, Y, R1, R2, R3, m and n are as defined above according to the present invention that is the compound of formula (1) wherein W is sulfur atom can be obtained by reacting the compound of formula (1-1) wherein A1, A2, A3, G, X, Y, R1, R2, R3, m and n are as defined above according to the present invention that is the compound of formula (1) wherein W is oxygen atom with a sulfurizing agent such as diphosphorus pentasulfide, diphosphorus pentasulfide-HMDO (hexamethyldisiloxane), Lawesson's Reagent (2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide), optionally by using a solvent inactive for the reaction, optionally in the presence of a base.
  • The reaction substrates can be used in an amount of 1 to 50 equivalents of the sulfurizing agent based on 1 equivalent of the compound of formula (1-1).
  • In case where a solvent is used, the solvent is not specifically limited if it dose not inhibit the progress of the reaction, but it includes for example aromatic hydrocarbons such as benzene, toluene, xylene or the like, aliphatic hydrocarbons such as hexane, heptane or the like, alicyclic hydrocarbons such as cyclohexane or the like, aromatic halogenated hydrocarbons such as chlorobenzene, dichlorobenzene or the like, aliphatic halogenated hydrocarbons such as dichloro methane, chloroform, carbon tetrachloride, 1,2-dichloroethane, 1,1,1-trichloroethane, trichloroethylene, tetrachloroethylene or the like, ethers such as diethyl ether, 1,2-dimethoxyethane, tetrahydrofuran, 1,4-dioxane or the like, amines such as triethyl amine, tributyl amine, N,N-dimethyl aniline or the like, pyridines such as pyridine, picoline or the like, and HMPA (hexamethylphosphoric triamide), and the like. These solvents may be used alone or in a mixture of two or more.
  • The addition of a base is not necessarily required. However, when the base is used, alkali metal carbonates such as sodium carbonate, potassium carbonate, sodium hydrogen carbonate or the like, organic bases such as triethyamine, tributylamine, N,N-dimethylaniline, pyridine, 4-(dimethylamino)pyridine, imidazole, 1,8-diazabicyclo[5.4.0]-7-undecene, and the like can be used in an amount of 1 to 10 equivalents based on the compound of formula (1-1).
  • The reaction temperature may be an arbitrary temperature ranging from 0° C. to the reflux temperature of a reaction mixture, and the reaction time may be an arbitrary time ranging from 5 minutes to 100 hours although it varies depending on the concentration of the reaction substrates or the reaction temperature.
  • Generally, it is preferable to carry out the reaction by using 1 to 10 equivalents of a sulfurizing agent such as diphosphorus pentasulfide, diphosphorus pentasulfide-HMDO, Lawesson's Reagent or the like, based on 1 equivalent of the compound of formula (1-1), optionally in the presence of 1 to 4 equivalents of a base such as sodium hydrogen carbonate, triethyamine, pyridine or the like, in a solvent such as benzene, toluene, chlorobenzene, dichloromethane, chloroform, 1,2-dimethoxyethane, tetrahydrofurane, 1,4-dioxane, HMPA or the like, at a temperature ranging from room temperature to the reflux temperature of the reaction mixture for 10 minutes to 50 hours, or in a solvent amount of pyridine at a temperature of 80° C. to the reflux temperature of the reaction mixture for 1 to 3 hours.
  • In Production Method A to Production Method D, the aimed compound of the present invention can be obtained by subjecting the reaction mixture after the completion of the reaction to ordinary post-treatment such as a direct concentration, or a concentration after dissolving in an organic solvent and washing with water or a concentration after placing in ice water and extracting with an organic solvent. In addition, when a purification is required, it can be separated and purified by an arbitrary purification process such as recrystallization, column chromatograph, thin layer chromatograph, liquid chromatograph collection or the like.
  • The compound of formula (5) used in Production Method A can be synthesized as follows, for example.
  • Figure US20150105398A1-20150416-C00033
  • That is, the compound of formula (5) wherein A1, A2, A3, G, X, Y, R3, m and n are as defined above can be obtained by reacting the compound of formula (12) wherein A1, A2, A3, G, X, Y, R3, m and n are as defined above, J4 is bromine atom, iodine atom, halosulfonyloxy (for example fluorosulfonyloxy), C1-C4haloalkylsulfonyloxy (for example trifluoromethane sulfonyloxy) or arylsulfonyloxy (for example benzenesulfonyloxy) according to a known method disclosed in documents, for example by CO insertion reaction by use of a transition metal catalyst such as palladium or the like stated in J. Org. Chem., 1999, vol. 64, p. 6921 or the like, or by a process by lithiation and then reaction with carbonic acid gas stated in Chem. Rev., 1990, vol. 90, p. 879.
  • In addition, the compound of formula (5) can be obtained by subjecting the compound of formula (12) to a reaction according to a reaction condition for CO insertion reaction by use of a transition metal catalyst such as palladium or the like stated in J. Org. Chem., 1974, vol. 39, p. 3318 or the like to convert the compound of formula (13) wherein A1, A2, A3, G, X, Y, R3, m and n are as defined above, Rb is C1-C6alkyl such as methyl, ethyl or the like, and then hydrolizing according to an ordinary ester hydrolysis disclosed in documents, for example a reaction condition stated in Angew. Chem., 1951, vol. 63, p. 329, J. Am. Chem. Soc., 1929, vol. 51, p. 1865 or the like.
  • Some of the compounds of formula (6) used in Production Method A are known compounds, and a part thereof is commercially available. Also, the compounds other than the above-mentioned compounds can be synthesized according to methods stated in for example Justus Liebigs Ann. Chem., 1979, p. 920, U.S. Pat. No. 5,990,323, WO 96/11200 or the like, and general synthetic methods for primary or secondary alkyl amines disclosed in documents.
  • The compounds of formula (8) used in Production Method B can be synthesized as follows, for example.
  • Figure US20150105398A1-20150416-C00034
  • That is, the compound of formula (8) wherein A1, A2, A3, W, Y, R1, R2 and n are as defined above can be easily synthesized by reacting the compound of formula (14) wherein A1, A2, A3, W, Y, R1, R2 and n are as defined above with hydroxyamine or the salt thereof according to known methods disclosed in documents, for example the method stated in J. Med. Chem., 2001, vol. 44, p. 2308 or the like.
  • The compounds of formula (10) used in Production Method B can be synthesized as follows, for example.
  • Figure US20150105398A1-20150416-C00035
  • That is, the compound of formula (10) wherein G, X, R3 and m are as defined above can be obtained by reacting the known compound of formula (15) wherein G, X and m are as defined above, J5 is bromine atom, iodine atom, C1-C4haloalkylsulfonyloxy (for example trifluoromethanesulfonyloxy), —B(OH)2, 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl, —Si(OEt)3, —ZnCl, —ZnBr or —ZnI, etc. with the compound of formula (16) wherein R3 is as defined above, J6 is halogen atom such as bromine atom, iodine atom or the like, or —B(OH)2 according to an ordinary crosscoupling reaction by use of a transition metal catalyst such as palladium or the like disclosed in documents, for example a reaction condtioin stated in J. Org. Chem., 1991, vol. 56, p. 7336, Tetrahedron Lett., 2001, vol. 42, p. 4083, or the like.
  • Some of the compounds of formula (16) used in the above-mentioned process are known compounds, and a part thereof is commercially available. Also, the compounds other than the above-mentioned compounds can be synthesized according to methods disclosed in documents, for example a method stated in J. Am. Chem. Soc., 1971, vol. 93, p. 1925, Tetrahedron Lett., 1990, vol. 31, p. 1919 and 2001, vol. 42, p. 4083 or the like.
  • In addition, the compounds of formula (10) can be obtained by reacting the compound of formula (17) wherein G, X, R3 and m are as defined above according to a reaction of converting carbonyl to olefine disclosed in documents, for example areaction condition stated in J. Org. Chem., 1986, vol. 51, p. 5252 and 1994, vol. 59, p. 2898, Synthesis, 1991, p. 29, Tetrahedron Lett., 1985, vol. 26, p. 5579 or the like.
  • Some of the compounds of formula (11) used in Production method C are known compounds, and a part thereof is commercially available. Also, the compounds other than the above-mentioned compounds can be easily synthesized according to methods disclosed in documents, for example a method stated in Chem. Lett., 1976, p. 373, J. Am. Chem. Soc., 1964, vol. 86, p. 4383, J. Org. Chem., 1976, vol. 41, p. 4028 and 1978, vol. 43, p. 3244, Org. Synth., 1988, Corrective vol. 6, p. 101, Tetrahedron Lett., 1972, p. 4339, GB 2,161,802, EP 0,051,273 or the like.
  • The compounds of formula (12) can be synthesized as follows, for example.
  • Figure US20150105398A1-20150416-C00036
  • That is, the compounds of formula (12) wherein A1, A2, A3, G, X, Y, R3, m, n and J4 are as defined above can be obtained by halogenating the compound of formula (18) wherein A1, A2, A3, Y, n and J4 are as defined above under a condition similar to that of Production Method B to obtain the compound of formula (19) wherein A1, A2, A3, Y, n, J3 and J4 are as defined above, and then reacting it with the compound of formula (10) wherein G, X, R3 and m are as defined above.
  • The compound of formula (18) can be easily synthesized by use of the corresponding known substituted aromatic aldehyde similarly to the process described in Reaction Scheme 2.
  • The compound of formula (14) can be synthesized for example acccording to Reaction Scheme 5 or Reaction Scheme 6.
  • Figure US20150105398A1-20150416-C00037
  • The compounds of formula (14) wherein A1, A2, A3, W, Y, R1, R2 and n are as defined above can be obtained by subjecting the compound of formula (20) wherein A1, A2, A3, W, Y, R1, R2, n and J4 are as defined above to CO insertion reaction according to known methods disclosed in documents, for example the reaction by use of a transition metal catalyst such as palladium or the like in the presence of hydride source such as formic acid or the like stated in Bull. Chem. Soc. Jpn., 1994, vol. 67, p. 2329, J. Am. Chem. Soc., 1986, vol. 108, p. 452, or the like.
  • Figure US20150105398A1-20150416-C00038
  • The compounds of formula (14-1) wherein A1, A2, A3, Y, R1, R2 and n are as defined above that are the compounds of formula (14) wherein W is oxygen atom can be synthesized by reacting the known compound of formula (21) wherein A1, A2, A3, Y and n are as defined above with the compound of formula (6) wherein R1 and R2 are as defined above by use of the method similar to Production Method A.
  • The compounds of formula (17) can be synthesized as follows, for example.
  • Figure US20150105398A1-20150416-C00039
  • That is, the compounds of formula (17) wherein X, R3 and m are as defined above, G is benzene ring can be obtained by reacting the known compound of formula (23) wherein X and m are as defined above, G is benzene ring with the known compound of formula (24) wherein R3 is as defined above, J7 is a leaving group such as halogen atom, trifluoromethanesulfonyloxy, 2-pyridyloxy or the like, or the known compound of formula (25) wherein R3 is as defined above according to a general acylating reaction of aromatic ring disclosed in documents, for example a method stated in Chem. Lett., 1990, p. 783, J. Org. Chem., 1991, vol. 56, p. 1963 or the like.
  • In addition, the compound of formula (17) wherein G, X, R3 and m are as defined above can be obtained according to general methods disclosed in documents for example by a method stated in J. Am. Chem. Soc., 1955, vol. 77, p. 3657, Tetrahedron Lett., 1980, vol. 21, p. 2129 and 1991, vol. 32, p. 2003, U.S. Pat. No. 5,514,816 in which the compound of formula (26) wherein G, X and m are as defined above, J8 is bromine atom or iodine atom is lithiated and the resulting compound is reacted with the known compound of formula (27) wherein R3 is as defined above, J9 is halogen atom, hydroxy, metal salt (for example, —OLi, —ONa), C1-C4alkoxy (for example, methoxy, ethoxy), di(C1-C4alkyl)amino (for example, diethylamino), C1-C4alkoxy C1-C4alkyl amino(for example O,N-dimethylhydroxyamino) or cyclic amino (for example, piperidin-1-yl, morpholin-4-yl, 4-methylpiperadin-1-yl), or the known compound of formula (25), or by a method stated in Heterocycles, 1987, vol. 25, p. 221, Synth. Commun., 1985, vol. 15, p. 1291 and 1990, vol. 20, p. 1469, DE 19727042, or the like in which a Grignard reagent is formed and then it is reacted with the compound of formula (27) or the compound of formula (25).
  • The compounds of formula (20) can be synthesized according to for example Reaction Scheme 8 or Reaction Scheme 9.
  • Figure US20150105398A1-20150416-C00040
  • The compounds of formula (20-1) wherein A1, A2, A3, Y, R1, R2, n and J4 are as defined above that are the compounds of formula (20) wherein W is oxygen atom can be obtained by reacting the known compound of formula (28) wherein A1, A2, A3, Y, n and J4 are as defined above with the compound of formula (6) wherein R1 and R2 are as defined above by use of the method similar to Production Method A.
  • Figure US20150105398A1-20150416-C00041
  • The compounds of formula (20-2) wherein A1, A2, A3, Y, R1, R2, n and J5 are as defined above that are the compounds of formula (20) wherein W is sulfur atom can be obtained by reacting the compound of formula (20-1) wherein A1, A2, A3, Y, R1, R2, n and J4 are as defined above that are the compounds of formula (20) wherein W is oxygen atom with a sulfurizing agent such as diphosphorus pentasulfide, diphosphorus pentasulfide-HMDO (hexamethyldisiloxane), Lawesson's Reagent (2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide) under a condition similar to that of Production Method D.
  • In each reaction, after the completion of the reaction, each production intermediate that is a starting compound in Production Method A to Produciton Method C can be obtained by carrying out normal post-treatments.
  • In addition, each production intermediate produced by the above-mentioned methods can be used for the following reaction step as such without isolation or purification.
  • The active compounds included in the present invention concretely include for example the compounds shown in Tables 2 and 3. The compounds that can be used as novel production intermediates for producing the active compounds included in the present invention concretely include for example the compounds shown in Tables 4 to 6. In the interim, the compounds shown in Tables 2 to 6 are for purposes of illustration and the present invention is not limited thereto.
  • In the meantime, in Tables, the indication “Et” means ethyl, hereinafter similarly thereto, “n-Pr” and “Pr-n” mean normal propyl, “i-Pr” and “Pr-i” mean isopropyl, “c-Pr” and “Pr-c” mean cyclopropyl, “n-Bu” and “Bu-n” mean normal butyl, “s-Bu” and “Bu-s” mean secondary butyl, “i-Bu” and “Bu-i” mean isobutyl, “t-Bu” and “Bu-t” mean tertiary butyl, “c-Bu” and “Bu-c” mean cyclobutyl, “n-Pen” and “Pen-n” mean normal pentyl, “c-Pen” and “Pen-c” mean cyclopentyl, “n-Hex” and “Hex-n” mean normal hexyl, “c-Hex” and “Hex-c” mean cyclohexyl, “Hept” means heptyl, “Oct” means octyl, “Ph” means phenyl, “1-Naph” means 1-naphthyl, “2-Naph” means 2-naphthyl, and in Tables, aromatic heterocyclic rings of D-1a to D-65a are the following structures, respectively
  • Figure US20150105398A1-20150416-C00042
    Figure US20150105398A1-20150416-C00043
    Figure US20150105398A1-20150416-C00044
    Figure US20150105398A1-20150416-C00045
    Figure US20150105398A1-20150416-C00046
    Figure US20150105398A1-20150416-C00047
    Figure US20150105398A1-20150416-C00048
    Figure US20150105398A1-20150416-C00049
    Figure US20150105398A1-20150416-C00050
    Figure US20150105398A1-20150416-C00051
    Figure US20150105398A1-20150416-C00052
    Figure US20150105398A1-20150416-C00053
  • For example, the indication “[CH2 (D-17a)CH3]” means 1-methylpyrazol-5-yl methyl, the indication “[CH2 (D-22b)CH3] means 2-methylthiazol-4-yl methyl. In addition, aliphatic heterocyclic rings of E-4-a to E-43b are the following structures, respectively
  • Figure US20150105398A1-20150416-C00054
    Figure US20150105398A1-20150416-C00055
    Figure US20150105398A1-20150416-C00056
    Figure US20150105398A1-20150416-C00057
    Figure US20150105398A1-20150416-C00058
  • For example, the indication “[CH2 (E-10b)CH3]” means 2-methyl-1,3-dioxolan-2-yl methyl, the indication “[CH2 (E-8a)CH3]” means N-methylpyrrolidin-2-yl methyl. Further, in Tables, partially saturated heterocyclic rings of M-2a to M-16a are the following structures, respectively
  • Figure US20150105398A1-20150416-C00059
  • For example, the indication “[CH2 (M-5a)CH3]” means 3-methyl-4,5-dihydroisoxazol-5-yl methyl.
  • Further, in Tables, T-1 to T-49 are the following structures, respectively
  • Figure US20150105398A1-20150416-C00060
    Figure US20150105398A1-20150416-C00061
    Figure US20150105398A1-20150416-C00062
    Figure US20150105398A1-20150416-C00063
  • Lengthy table referenced here
    US20150105398A1-20150416-T00001
    Please refer to the end of the specification for access instructions.
  • Lengthy table referenced here
    US20150105398A1-20150416-T00002
    Please refer to the end of the specification for access instructions.
  • Lengthy table referenced here
    US20150105398A1-20150416-T00003
    Please refer to the end of the specification for access instructions.
  • Lengthy table referenced here
    US20150105398A1-20150416-T00004
    Please refer to the end of the specification for access instructions.
  • Lengthy table referenced here
    US20150105398A1-20150416-T00005
    Please refer to the end of the specification for access instructions.
  • The compounds of the present invention can effectively control in a low concentration so-called agricultural insects injuring agricultural and horticultural crops and trees, so-called domestic animal pests parasitizing domestic animals and domestic fowls, so-called hygienic pests having an adverse affect on human being's environment such as houses, insects as so-called stored grain insects injuring grains and the like stored in storehouses, and any pests of acarids, crustaceans, mollusks and nematodes generating in the similar scenes.
  • The insects, acarids, crustaceans, mollusks and nematodos that the compounds of the present invention can control concretely include for example the followings: Lepidoptera insects, such as Adoxophyes honmai, Adoxophyes orana faciata, Archips breviplicanus, Archips fuscocupreanus, Grapholita molesta, Homona magnanima, Leguminivora glycinivorella, Matsumuraeses phaseoli, Pandemis heparana, Bucculatrix pyrivorella, Lyonetia clerkella, Lyonetia prunifoliella malinella, Caloptilia theivora, Phyllonorycter ringoniella, Phyllocnistis citrella, Acrolepiopsis sapporensis, Acrolepiopsis suzukiella, Plutella xylostella, Stathmopoda masinissa, Helcystogramma triannulella, Pectinophora gossypiella, Carposina sasakii, Cydla pomonella, Chilo suppressalis, Cnaphalocrocis medinalis, Conogethes punctiferalis, Diaphania indica, Etiella zinckenella, Glyphodes pyloalis, Hellula undalis, Ostrinia furnacalis, Ostrinia scapulalis, Ostrinia nubilalis, Parapediasia teterrella, Parnara guttata, Pieris brassicae, Pieris rapae crucivora, Ascotis selenaria, Pseudoplusia includens, Euproctis pseudoconspersa, Lymantria dispar, Orgyia thyellina, Hyphantria cunea, Lemyra imparilis, Adris tyrannus, Aedia leucomelas, Agrotis ipsilon, Agrotis segetum, Autographa nigrisigna, Ctenoplusia agnata, Helicoverpa armigera, Helicoverpa assulta, Helicoverpa zea, Heliothis virescens, Mamestra brassicae, Mythimna separata, Naranga aenescens, Spodoptera eridania, Spodoptera exigua, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, Spodoptera depravata, Trichoplusia ni, Endopiza viteana, Manduca quinquemaculata, Manduca sexta, or the like;
  • Thysanoptera insects, such as Frankliniella intonsa, Frankliniella occidentalis, Heliothrips haemorrhoidalis, Scirtothrips dorsalis, Thrips palmi, Thrips tabaci, Ponticulothrips diospyrosis, or the like;
    Hemiptera insects, such as Dolycoris baccarum, Eurydema rugosum, Eysarcoris aeneus, Eysarcoris lewisi, Eysarcoris ventralis, Glaucias subpunctatus, Halyomorpha halys, Nezara antennata, Nezara viridula, Piezodorus hybneri, Plautia crossota, Scotinophora lurida, Cletus punctiger, Leptocorisa chinensis, Riptortus clavatus, Rhopalus msculatus, Cavelerius saccharivorus, Togo hemipterus, Dysdercus cingulatus, Stephanitis pyrioides, Halticus insularis, Lygus lineolaris, Stenodema sibiricum, Stenotus rubrovittatus, Trigonotylus caelestialium, Arboridia apicalis, Balclutha saltuella, Epiacanthus stramineus, Empoasca fabae, Empoasca nipponica, Empoasca onukii, Empoasca sakaii, Macrosteles striifrons, Nephotettix cinctinceps, Psuedatomoscelis seriatus, Laodelphax striatella, Nilaparvata lugens, Sogatella furcifera, Diaphorina citri, Psylla pyrisuga, Aleurocanthus spiniferus, Bemisia argentifolii, Bemisia tabaci, Dialeurodes citri, Trialeurodes vaporariorum, Viteus vitifolii, Aphis gossypii, Aphis spiraecola, Myzus persicae, Toxoptera aurantii, Drosicha corpulenta, Icerya purchasi, Phenacoccus solani, Planococcus citri, Planococcus kuraunhiae, Pseudococcus comstocki, Ceroplastes ceriferus, Ceroplastes rubens, Aonidiella aurantii, Comstockaspis perniciosa, Fiorinia theae, Pseudaonidia paeoniae, Pseudaulacaspis pentagona, Pseudaulacaspis prunicola, Unaspis euonymi, Unaspis yanonensis, Cimex lectularius, or the like;
    Coleoptera insects, such as Anomala cuprea, Anomala rufocuprea, Gametis jucunda, Heptophylla picea, Popillia japonica, Lepinotarsa decemlineata, Melanotus fortnumi, Melanotus tamsuyensis, Lasioderma serricorne, Epuraea domina, Epilachna varivestis, Epilachna vigintioctopunctata, Tenebrio molitor, Tribolium castaneum, Anoplophora malasiaca, Monochamus alternatus, Psacothea hilaris, Xylotrechus pyrrhoderus, Callosobruchus chinensis, Aulacophora femoralis, Chaetocnema concinna, Diabrotica undecimpunctata, Diabrotica virgifera, Diabrotica barberi, Oulema oryzae, Phyllotreta striolata, Psylliodes angusticollis, Rhynchites heros, Cylas formicarius, Anthonomus grandis, Echinocnemus squameus, Euscepes postfasciatus, Hypera postica, Lissohoptrus oryzophilus, Otiorhynchus sulcatus, Sitophilus granarius, Sitophilus zeamais, Sphenophorus venatus vestitus, Paederus fuscipes, or the like;
    Diptera insects, such as Asphondylia yushimai, Sitodiplosis mosellana, Bactrocera cucurbitae, Bactrocera dorsalis, Ceratitis capitata, Hydrellia griseola, Drosophila suzukii, Agromyza oryzae, Chromatomyia horticola, Liriomyza bryoniae, Liriomyza chinensis, Liriomyza sativae, Liriomyza trifolii, Delia platura, Pegomya cunicularia, Rhagoletis pomonella, Mayetiola destructor, Musca domestica, Stomoxys calcitrans, Melophagus ovinus, Hypoderma bovis, Hypoderma lineatum, Oestrus ovis, Glossina palpalis, Glossina morsitans, Prosimulium yezoensis, Tabanus trigonus, Telmatoscopus albipunctatus, Leptoconops nipponensis, Culex pipiens pallens, Aedes aegypti, Aedes albopicutus, Anopheles hyracanus sinesis, or the like;
    Hymenoptera insects, such as Apethymus kuri, Athalia rosae, Arge pagana, Neodiprion sertifer, Dryocosmus kuriphilus, Eciton burchelli, Eciton schmitti, Camponotus japonicus, Vespa mandarina, Myrmecia spp., Solenopsis spp., Monomorium pharaonis, or the like;
    Orthoptera insects, such as Teleogryllus emma, Gryllotalpa orientalis, Locusta migratoria, Oxya yezoensis, Schistocerca gregaria, or the like;
    Collembola insects, such as Onychiurus folsomi, Onychiurus sibiricus, Bourletiella hortensis, or the like;
    Dictyoptera insect, such as Periplaneta fuliginosa, Periplaneta japonica, Blattella germanica, or the like;
    Isoptera insects, such as Coptotermes formosanus, Reticulitermes speratus, Odontotermes formosanus, or the like;
    Siphonaptera insects, such as Ctenocephalidae felis, Ctenocephalides canis, Echidnophaga gallinacea, Pulex irritans, Xenopsylla cheopis, or the like;
    Mallophaga insects, such as Menacanthus stramineus, Bovicola bovis, or the like;
    Anoplura insects, such as Haematopinus eurysternus, Haematopinus suis, Linognathus vituli, Solenopotes capillatus, or the like;
    Tarsonemid mites, such as Phytonemus pallidus, Polyphagotarsonemus latus, Tarsonemus bilobatus, or the like;
    Eupodid mites, such as Penthaleus erythrocephalus, Penthaleus major, or the like;
    Spider mites, such as Oligonychus shinkajii, Panonychus citri, Panonychus mori, Panonychus ulmi, Tetranychus kanzawai, Tetranychus urticae, or the like;
    Eriophyid mites, such as Acaphylla theavagrans, Aceria tulipae, Aculops lycopersici, Aculops pelekassi, Aculus schlechtendali, Eriophyes chibaensis, Phyllocoptruta oleivora, or the like;
    Acarid mites, such as Rhizoglyphus robini, Tyrophagus putrescentiae, Tyrophagus similis, or the like;
    Bee brood mites, such as Varroa jacobsoni, or the like;
    Ixodides, such as Boophilus microplus, Rhipicephalus sanguineus, Haemaphysalis longicornis, Haemophysalis flava, Haemophysalis campanulata, Ixodes ovatus, Ixodes persulcatus, Amblyomma spp., Dermacentor spp., or the like;
    Cheyletidae, such as Cheyletiella yasguri, Cheyletiella blakei, or the like;
    Demodicidae, such as Demodex canis, Demodex cati, or the like;
    Psoroptidae, such as Psoroptes ovis, or the like;
    Scarcoptidae, such as Sarcoptes scabiei, Notoedres cati, Knemidocoptes spp., or the like;
    Crustacea, such as Armadillidium vulgare, or the like;
    Gastropoda, such as Pomacea canaliculata, Achatina fulica, Meghimatium bilineatum, Limax Valentiana, Acusta despecta sieboldiana, Euhadra peliomphala, or the like;
    Nematodes, such as Prathylenchus coffeae, Prathylenchus penetrans, Prathylenchus vulnus, Globodera rostochiensis, Heterodera glycines, Meloidogyne hapla, Meloidogyne incognita, Aphelenchoides besseyi, Bursaphelenchus xylophilus, or the like. But the present invention is not limited thereto.
  • The endo-parasites of domestic animals, domestic fowls, pets and the like that the compounds of the present invention can control concretely include for example the followings:
  • Nematodes, such as Haemonchus, Trichostrongylus, Ostertagia, Nematodirus, Cooperia, Ascaris, Bunostomum, Oesophagostomum, Chabertia, Trichuris, Storongylus, Trichonema, Dictyocaulus, Capillaria, Heterakis, Toxocara, Ascaridia, Oxyuris, Ancylostoma, Uncinaria, Toxascaris, Parascaris, or the like;
    Filariidae in nematodes, such as Wuchereria, Brugia, Onchoceca, Dirofilaria, Loa, or the like;
    Dracunculidae in nematodes, such as Deacunculus, or the like;
    Cestoda, such as Dipylidium caninum, Taenia taeniaeformis, Taenia solium, Taenia saginata, Hymenolepis diminuta, Moniezia benedeni, Diphyllobothrium latum, Diphyllobothrium erinacei, Echinococcus granulosus, Echinococcus multilocularis, or the like;
    Trematoda, such as Fasciola hepatica, F. gigantica, Paragonimus westermanii, Fasciolopsic bruski, Eurytrema pancreaticum, E. coelomaticum, Clonorchis sinensis, Schistosoma japonicum, Schistosoma haematobium, Schistosoma mansoni, or the like;
    Eimeria spp., such as Eimeria tenella, Eimeria acervulina, Eimeria brunetti, Eimeria maxima, Eimeria necatrix, Eimeria bovis, Eimeria ovinoidalis, or the like;
    Trypanosomsa cruzi, Leishmania spp., Plasmodium spp., Babesis spp., Trichomonadidae spp., Histomanas spp., Giardia spp., Toxoplasma spp., Entamoeba histolytica, Theileria spp., or the like. But the present invention is not limited thereto.
  • Further, the compounds of the present invention are effective for pests acquiring high resistance against existing insecticides such as organic phosphorus compounds, carbamate compounds or pyrethroid compounds, etc.
  • That is, the compounds of the present invention can effectively control pests that belong to insects such as Collembola, Dictyoptera, Orthoptera, Isoptera, Thysanoptera, Hemiptera, Lepidoptera, Coleoptera, Hymenoptera, Diptera, Isoptera and Anoplura, Acarina, Gastropoda and Nematoda, in a low concentration. On the other hand, the compounds of the present invention have an extremely useful charactristic that they have little adverse affect on mammals, fishes, crustaceans and useful insects (beneficial insect such as honeybee, bumblebee or the like, or, natural enemies such as Aphytis lingnanensis, Aphidius colemani, Orius strigicollis, Amblyseius californicus, or the like).
  • When the compounds of the present invention are used, they can be generally mixed with a suitable solid carrier or liquid carrier, optionally along with surfactant, penetrating agent, spreading agent, thickner, anti-freezing agent, binder, anti-caking agent, disintegrating agent, anti-foaming agent, preservative, stabilizer, and the like, and can be formulated into any desired forms for practical use, such as soluble concentrates, emulsifiable concentrates, wettable powders, water soluble powders, water dispersible granules, water soluble granules, suspension concentrates, concentrated emulsions, suspoemulsions, microemulsions, dustable powders, granules, tablets and emulsifiable gels. From the viewpoint of an elimination or reduction of labor and an improvement of safety, the formulations in any desired forms described above may be included into a water-soluble bag made of water-soluble capsule or water-soluble film.
  • The solid carrier includes, for example, natural minerals such as quartz, calcite, sepiolite, dolomaite, chalk, kaolinite, pyrofilite, celicite, halocite, methahalocite, kibushi clay, gairome clay, pottery stone, zeaklite, allophane, white sand, mica, talc, bentonite, activeted earth, acid china clay, pumice, attapulgite, zeolite and diatomaceous earth, etc., calcined products of natural minerals such as calcined clay, perlite, white sand balloon (loam balloon), vermiculite, attapulgus clay and calcined diatomaceous earth, etc., inorganic salts such as magnesium carbonate, calcium carbonate, sodium carbonate, sodium hydrogen carbonate, ammonium sulfate, sodium sulfate, magnesium sulfate, diammonium hydrogen phosphate, ammonium dihydrogen phosphate and potassium chloride, etc., saccharides such as glucose, fructose, sucrose and lactose, etc., polysaccharides such as starch, powder cellulose and dextrin, etc., organic materials such as urea, urea derivatives, benzoic acid and a salt of benzoic acid, etc., plants such as wood powder, cork powder, corn head stem, walnut shell and tobacco stem, etc., fly ash, white carbon (e.g., hydrated synthetic silica, anhydrous synthetic silica and hydrated synthetic silicate, etc.) and feritilizers, etc.
  • As the liquid carrier, there may be mentioned, for example, aromatic hydrocarbons such as xylene, alkyl(C9 or C10, etc.)benzene, phenylxylylethane and alkyl(C1 or C3, etc.)naphthalene, etc., aliphatic hydrocarbons such as machine oil, normal paraffin, isoparaffin and naphthene, etc., a mixture of aromatic hydrocarbons and aliphatic hydrocarbons such as kerosene, etc., alcohols such as ethanol, isopropanol, cyclohexanol, phenoxyethanol and benzylalcohol, etc., polyvalent alcohols such as ethylene glycol, propyleneglycol, diethylene glycol, hexylene glycol, polyethylene glycol and polypropyleneglycol, etc., ethers such as propyl cellosolve, butyl cellosolve, phenyl cellosolve, propyleneglycol monomethyl ether, propyleneglycol monoethyl ether, propyleneglycol monopropyl ether, propyleneglycol monobutyl ether and propyleneglycol monophenyl ether, etc., ketones such as acetophenone, cyclohexanone and -butyrolactone, etc., esters such as aliphatic acid methyl ester, dialkyl succinate, dialkyl glutamate, dialkyl adipate and dialkyl phthalate, etc., acid amides such as N-alkyl(C1, C8 or C12, etc.)pyrrolidone, etc., oil and fats such as soybean oil, linseed oil, rapeseed oil, coconut oil, cottonseed oil and caster oil, etc., dimethylsulfoxide and water.
  • These solid and liquid carriers may be used alone or in combination of two or more kinds in combination.
  • As the surfactant, there may be mentioned, for example, nonionic surfactants such as polyoxyethylene alkyl ether, polyoxyethylene alkyl (mono- or di-)phenyl ether, polyoxyethylene (mono-, di- or tri-)styrylphenyl ether, polyoxyethylene polyoxypropylene block copolymer, polyoxyethylene fatty acid (mono- or di-)ester, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, caster oil-ethylene oxide adducts, acetylene glycol, acetylene alcohol, ethylene oxide adducts of acetylene glycol, ethylene oxide adducts of acetylene alcohol and alkyl glycoside, etc., anionic surfactants such as alkyl sulfate, alkylbenzenesulfonate, lignine sulfonate, alkylsulfosuccinate, naphthalene sulfonate, alkylnaphthalene sulfonate, formalin condensate salt of naphthalene sulfonic acid, formalin condensate salt of alkylnaphthalene sulfonic acid, polyoxyethylene alkyl ether sulfate or phosphate, polyoxyethylene (mono- or di-)alkylphenyl ether sulfate or phosphate, polyoxyethylene (mono-, di- or tri-)styrylphenyl ether sulfate or phosphate, polycarboxylate (e.g., polyacryaltes, polymaleates and copolymer materials of maleic acid and olefin, etc.) and polystyrenesulfonate, etc., cationic surfactants such as alkylamine salt and alkyl quaternary ammonium salt, etc., amphoteric surfactants such as amino acid type and betaine type, etc., silicone type surfactants and fluorine type surfactants.
  • A content of these surfactants is not specifically limited, and it is desirably in the range of 0.05 to 20 parts by weight in general based on 100 parts by weight of the preparation according to the present invention. Also, these surfactants may be used alone or in combination of two or more kinds in combination.
  • A dose of the compound of the present invention to be applied may vary depending on the place to be applied, time to be applied, method to be applied, crops to cultivate, etc., and in general, it is suitable in an amount of about 0.005 to 50 kg or so per a hectare (ha) as an amount of the effective ingredient.
  • On the other hand, when the compound of the present invention is used for controlling ecto- or endo-parasites of mammals and birds as domestic animals and pets, the effective amount of the compound of the present invention together with additives for formulations can be administered through oral administration, parenteral administration such as injection (intramuscular, subcutaneous, intravenous, intraperitoneal) or the like; transdermal administration such as dipping, spray, bathing, washing, pouring-on and spotting-on, and dusting, or the like; transnasal administration. The compound of the present invention can be also administered through a formed product by use of a strip, a plate, a band, a collar, an ear mark, a limb band, a labe apparatus, or the like. In administration, the compound of the present invention can be formed in an arbitrary dosage form that is suited for the administration route.
  • The arbitrary dosage form includes solid preparations such as a dustable powder, a granule, wettable powder, a pellete, a tablet, a bolus, a capsule, a formed product containing an active compound; liquid formulations such as an injectable liquid formulation, an oral liquid formulation, a liquid formulation used on skin or in body cavity; solution preparations such as a pour-on agent, a spot-on agent, a flowable agent, an emulsifiable concentrate; semi-solid preparations such as an ointment, gel or the like.
  • The solid preparations can be mainly used through oral administration or transdermal administratin by diluting with water or the like, or by environmental treatment. The solid preparations can be prepared by mixing the active compound with suitable excipients and optionally auxiliary substances and converting to a desired form. The suitable excipients include for example inorganic substances such as carbonates, hydrogen carbonates, phosphates, aluminum oxide, silica, clay or the like, organic substances such as sugar, cellulose, milled cereal, starch or the like.
  • The injectable liquid formulation can be administered intravenously, intramuscularly and subcutaneously. The injectable liquid formulation can be prepared by dissolving an acitve compound in a suitable solvent and optionally by adding an additive such as a solubilizing agent, an acid, a base, a buffering salt, an antioxidant, and a protective agent or the like. Suitable solvent is for example water, ethanol, butanol, benzyl alcohol, glycerin, propylene glycol, poethylene glycol, N-methylpyrrolidone, and a mixture thereof, a physiologically permissible vegetable oil, a synthetic oil suitable for injection, or the like. The solubilizing agent includes polyvinyl pyrrolidone, polyoxyethylated castor oil and polyoxyethylated sorbitan ester, or the like. The protective agent includes benzyl alcohol, trichlorobutanol, p-hydroxybenzoic acid ester and n-butanol or the like.
  • The oral liquid formulation can be administered directly or after dilution. It can be prepared similarly to the injectable liquid formulation.
  • The flowable agent and the emulsifiable concentrate can be administered directly or after dilution through transdermal administration or environmental treatment.
  • The liquid formulation used on skin can be administered by pouring on, spreading, rubbing, atomizing, spraying, or dipping (dipping, bathing or washing). These liquid can be prepared similarly to the injectable liquid formulation.
  • The pour-on agent and the spot-on agent are poured or atomized on the limited spot on the skin, thereby the active compound can be penetrated into the skin and act in the whole body. The pour-on agent and the spot-on agent can be prepared by dissolving, suspending or emulsifying an active ingredient in a suitable skin-fitted solvent or solvent mixture. If required, an auxiliary substance such as a surfactant, a colorant, an absorption promoting agent, an antioxidant, a light stabilizer and an adhesive, etc. may be added.
  • Suitable solvent includes water, alkanol, glycol, polyethylene glycol, polypropylene glycol, glycerin, benzyl alcohol, phenylethanol, phenoxyethanol, ethyl acetate, butyl acetate, benzyl benzoate, dipropylene glycol monomethyl ether, diethylene glycol monobutyl ether, acetone, methyl ethyl ketone, aromatic and/or aliphatic hydrocarbon, vegetable or synthetic oil, DMF, liquid paraffin, light-duty liquid paraffin, silicone, dimethylacetamide, N-methylpyrrolidone or 2,2-dimethyl-4-oxy-methylene-1,3-dioxolane. The absorption promoting agent includes DMSO, isopropyl myristate, dipropylene glycol pelargonate, silicone oil, aliphatic ester, triglyceride and fatty alcohol. The antioxidant includes sulfite, metabisulfite, ascorbic acid, butylhydroxytoluene, butylhydroxyanisole and tocopherol.
  • The emusifiable concentrate can be administrated orally, subcutaneously or injectably. The emusifiable concentrate can be prepared by dissolving an active ingredient in a hydrophobic phase or a hydrophilic phase, and then homogenating the resulting solution with a suitable emulsifying agent optionally with further an auxiliary substance such as a colorant, an absortion promoting agent, a protective agent, an antioxidant, a light screen and a thickening agent.
  • The hydrophobic phase (oil) includes paraffin oil, silicone oil, sesame-seed oil, oil of almonds, castor oil, synthetic triglyceride, ethyl stearate, di-n-butyryl adipate, hexyl laurate, dipropylene glycol pelargonate, ester of branched short chain length aliphatic acid with saturated aliphatic acid of chain length C16 to C18, isopropyl myristate, isopropyl palmitate, capryl/caprylic acid ester of saturated fatty alcohol of chain length C12 to C18, isopropyl stearate, oleyl oleate, decyl oleate, ethyl oleate, ethyl lactate, wax-like fatty acid ester, dibutyl phthalate, diisopropyl adipate, isotridecyl alcohol, 2-octyldodecanol, cetylstearyl alcohol, oleyl alcohol.
  • The hydrophilic phase includes water, propylene glycol, glycerin, sorbitol.
  • The emulsifying agent includes non-ionic surfactants such as polyoxyethylated castor oil, polyoxyethylated sorbitan mono-olefinate, sorbitan monostearate, glycerin monostearate, polyoxyethyl stearate, alkylphenol polyglycol ether; amphoteric surfactants such as di-sodium N-lauryl-iminodipropionate, lecithin or the like; anionic surfactants such as sodium lauryl sulfate, fatty alcohol sulfric acid ether, monoethanol amine salt of mono/dialkylpolyglycol orthophosphate or the like; cationic surfactants such as cetyl chloride trimethylammonium or the like.
  • The other auxiliary substance includes carbocymethylcellulose, methylcellulose, polyacrylate, arginate, gelatin, gum arabic, polyvinyl pyrrolidone, polyvinyl alcohol, methylvinyl ether, copolymer of maleic anhydride, polyethylene glycol, wax, colloidal silica.
  • The semi-solid preparation can be administered by coating or spreading on the skin, or by introducing in body cavity. The gel can be prepared by adding a thickener in an amount enough to provide a clear substance having a viscosity of ointment in a solution prepared for the injectable liquid formulation as mentioned above.
  • Next, formulation examples of the preparation in case where the compound of the present invention is used are shown below. Provided that formulation examples of the present invention are not limited only thereto. In the interim, in the following Formulation Examples, “part(s)” mean part(s) by weight.
    • (Wettable Powder)
  • Compound of the present invention 0.1 to 80 parts
    Solid carrier 5 to 98.9 parts
    Surfactant 1 to 10 parts
    Others 0 to 5 parts

    As other components, there may be mentioned, for example, a non-caking agent, a decomposition preventing agent, and the like.
    • (Emulsifiable Concentrate)
  • Compound of the present invention 0.1 to 30 parts
    Liquid carrier 45 to 95 parts
    Surfactant 4.9 to 15 parts
    Others 0 to 10 parts

    As other components, there may be mentioned, for example, a spreading agent, a decomposition preventing agent, and the like.
    • (Suspension Concentrate)
  • Compound of the present invention 0.1 to 70 parts
    Liquid carrier 15 to 98.89 parts
    Surfactant 1 to 12 parts
    Others 0.01 to 30 parts

    As other components, there may be mentioned, for example, an antifreezing agent, a thicknening agent, and the like.
    • (Water Dispersible Granule)
  • Compound of the present invention 0.1 to 90 parts
    Solid carrier 0 to 98.9 parts
    Surfactant 1 to 20 parts
    Others 0 to 10 parts

    As other components, there may be mentioned, for example, a binder, a decomposition preventing agent, and the like.
    • (Soluble Concentrate)
  • Compound of the present invention 0.01 to 70 parts
    Liquid carrier 20 to 99.99 parts
    Others 0 to 10 parts

    As other components, there may be mentioned, for example, an antifreezing agent, a spreading agent, and the like.
    • (Granule)
  • Compound of the present invention 0.01 to 80 parts
    Solid carrier 10 to 99.99 parts
    Others 0 to 10 parts

    As other components, there may be mentioned, for example, a binder, a decomposition preventing agent, and the like.
    • (Dustable Powder)
  • Compound of the present invention 0.01 to 30 parts
    Solid carrier 65 to 99.99 parts
    Others 0 to 5 parts

    As other components, there may be mentioned, for example, a drift preventing agent, a decomposition preventing agent, and the like.
  • Next, formulation examples using the compound of the present invention as an effective ingredient are described in more detail, but the present invention is not limited thereto. In the interim, in the following Formulation Examples, “part(s)” mean part(s) by weight.
    • Formulation Example 1 Wettable Powder
  • Compound of the present invention No. 5-075 20 parts
    Pyrophylite 74 parts
    Solpol 5039  4 parts
    (A mixture of a nonionic surfactant and an anionic
    surfactant: available from TOHO
    Chemical Industry Co., LTD, Tradename)
    CARPREX #80D  2 parts
    (Synthetic hydrated silicic acid: available from
    Shionogi & Co., Ltd., Tradename)

    The above materials are uniformly mixed and pulverized to make wettable powder.
    • Formulation Example 2 Emulsion
  • Compound of the present invention No. 5-075  5 parts
    Xylene 75 parts
    N-methylpyrrolidone 15 parts
    Solpol 2680  5 parts
    (A mixture of a nonionic surfactant and an anionic
    surfactant: available from TOHO
    Chemical Industry Co., LTD, Tradename)

    The above materials are uniformly mixed to make emulsifiable concentrate.
    • Formulation Example 3 Suspension Concentrate
  • Compound of the present invention No. 5-075 25 parts
    Agrisol S-710 10 parts
    (a nonionic surfactant: available from KAO
    CORPORATION, Tradename)
    Lunox 1000C 0.5 part
    (an anionic surfactant: available from TOHO
    Chemical Industry Co., LTD, Tradename)
    Xanthan gum 0.2 part
    Water 64.3 parts

    The above materials are uniformly mixed, and then, wet pulverized to make suspension concentrate.
    • Formulation Example 4 Water Dispersible Granule
  • Compound of the present invention No. 5-075 75 parts
    HITENOL NE-15  5 parts
    (an anionic surfactant: available from DAI-ICHI
    KOGYO SEIYAKU CO., LTD., Tradename)
    VANILLEX N 10 parts
    (an anionic surfactant: available from Nippon
    Paper Chemicals Co., Ltd., Tradename)
    CARPREX #80D 10 parts
    (Synthetic hydrated silicic acid: available from
    Shionogi & Co., Ltd., Tradename)

    The above materials are uniformly mixed and pulverized, and then, a small amount of water is added to the mixture and the resulting mixture is mixed under stirring, granulated by an extrusion granulator, and dried to make water dispersible granule.
    • Formulation Example 5 Granule
  • Compound of the present invention No. 5-075  5 parts
    Bentonite 50 parts
    Talc 45 parts

    The above materials are uniformly mixed and pulverized, and then, a small amount of water is added to the mixture and the resulting mixture is mixed under stirring, granulated by an extrusion granulator, and dried to make granule.
    • Formulation Example 6 Dustable Powder
  • Compound of the present invention No. 5-075  3 parts
    CARPREX #80D 0.5 parts
    (Synthetic hydrated silicic acid: available from
    Shionogi & Co., Ltd., Tradename)
    Kaolinite  95 parts
    Diisopropyl phosphate 1.5 parts

    The above materials are uniformly mixed and pulverized to make dustable powder. When the formulation is used, it is sprayed by diluting with water in 1- to 1000-fold concentration, or directly without dilution.
    • Formulation Example 7 Wettable Powder Preparation
  • Compound of the present invention No. 5-086 25 parts
    Sodium diisobutylnaphthalenesulfonate 1 part
    Calcium n-dodecylbenzenesulfonate 10 parts
    Alkylaryl polyglycol ether 12 parts
    Sodium salt of naphthalenesulfonic acid formalin 3 parts
    condensate
    Emulsion type silicone 1 part
    Silicon dioxide 3 parts
    Kaoline 45 parts
    • Formulation Example 8 Water-Soluble Concentrate Preparation
  • Compound of the present invention No. 5-086 20 parts
    Polyoxyethylene lauryl ether 3 parts
    Sodium dioctylsulfosuccinate 3.5 parts
    Dimethylsulfoxide 37 parts
    2-Propanol 36.5 parts
    • Formulation Example 9 Liquid Formulation for Atomization
  • Compound of the present invention No. 5-086  2 parts
    Dimethylsulfoxide 10 parts
    2-Propanol 35 parts
    Acetone 53 parts
    • Formulation Example 10 Liquid Formulation for Transdermal Administration
  • Compound of the present invention No. 5-086  5 parts
    Hexylene glycol 50 parts
    Isopropanol 45 parts
    • Formulation Example 11 Liquid Formulation for Transdermal Administration
  • Compound of the present invention No. 5-086  5 parts
    Propylene glycol monomethyl ether 50 parts
    Dipropylene glycol 45 parts
    • Formulation Example 12 Liquid Formulation for Transdermal Administration (Pouring-on)
  • Compound of the present invention No. 5-086  2 parts
    Light-duty liquid paraffin 98 parts
    • Formulation Example 13 Liquid Formulation for Transdermal Administration (Pouring-on)
  • Compound of the present invention No. 5-086 2 parts
    Light-duty liquid paraffin 58 parts
    Olive oil 30 parts
    ODO-H 9 parts
    Shinetsu silicone 1 part
  • Also, when the compound of the present invention is used as an agricultural chemicals, it may be mixed with other kinds of herbicides, various kinds of insecticides, acaricides, nematocides, fungicides, vegetable growth regulators, synergists, fertilizers, soil improvers, etc., and applied, at the time of preparing the formulation or at the time of spreading, if necessary.
  • In particular, by mixing with the other agricultural chemicals or plant hormones and applying the mixture, it can be expected that a cost is reduced due to reduction in a dose to be applied, enlargement in insecticidal spectrum or higher prevention and extinction effect of noxious organisms due to synergistic effect by mixing agricultural chemicals. At this time, it is possible to use the compound with a plural number of the conventionally known agricultural chemicals in combination simultaneously. As the kinds of the agricultural chemicals to be used in admixture with the compound of the present invention, there may be mentioned, for example, the compounds described in Farm Chemicals Handbook, 1999 ed. and the like. Specific examples of the general names can be enumerated below, but the invention is not necessarily limited only thereto.
  • Fungicides: acibenzolar-5-methyl, acylaminobenzamide, amobam, ampropylos, anilazine, azaconazole, azoxystrobin, benalaxyl, benodanil, benomyl, benthiazole, benzamacril, binapacryl, biphenyl, bitertanol, bethoxazine, bordeaux mixture, blasticidin-S, bromoconazole, bupirimate, buthiobate, calcium polysulfide, captafol, captan, copper oxychloride, carpropamid, carbendazim, carboxin, CGA-279202 (test name), chinomethionat, chlobenthiazone, chlorfenazol, chloroneb, chlorothalonil, chlozolinate, cufraneb, cymoxanil, cyproconazol, cyprodinil, cyprofuram, dazomet, debacarb, dichlorophen, diclobutrazol, diclhlofluanid, diclomedine, dicloran, diethofencarb, diclocymet, difenoconazole, diflumetorim, dimethirimol, dimethomorph, diniconazole, diniconazole-M, dinocap, diphenylamine, dipyrithione, ditalimfos, dithianon, dodemorph, dodine, drazoxolon, edifenphos, epoxiconazole, etaconazole, ethirimol, etridiazole, famoxadone, fenarimol, febuconazole, fenamidone, fendazosulam, fenfuram, fenhexamid, fenpiclonil, fenpropidin, fenpropimorph, fentin, ferbam, ferimzone, fluazinam, fludioxonil, fluoroimide, fluquinconazole, flusilazole, flusulfamide, flutolanil, flutriafol, folpet, fosetyl-aluminium, fuberidazole, furalaxyl, furametpyr, guazatine, hexachlorobenzene, hexaconazole, hymexazol, imazalil, imibenconazole, iminoctadine, ipconazole, iprobenfos, iprodione, isoprothiolane, iprovalicarb, kasugamycin, kresoxim-methyl, mancopper, mancozeb, maneb, mepanipyrim, mepronil, metalaxyl, metconazole, methasulfocarb, metiram, metominostrobin, myclobutanil, MTF-753 (test name), nabam, nickel bis(dimethyldithiocarbamate), nitrothal-isopropyl, nuarimol, NNF-9425 (test name), octhilinone, ofurace, oxadixyl, oxycarboxin, oxpoconazole fumarate, pefurzoate, penconazole, pencycuron, phthalide, piperalin, polyoxins, potassium hydrogen carbonate, probenazole, prochloraz, procymidone, propamocarb hydrochloride, propiconazole, propineb, pyrazophos, pyrifenox, pyrimethanil, pyroquilon, quinomethionate, quinoxyfen, quintozene, RH 7281 (test name), sodium hydrogen carbonate, sodium hypochlorite, sulfur, spiroxamine, tebuconazole, tecnazene, tetraconazole, thiabendazole, thiadiazin/milneb, thifluzamide, thiophanate-methyl, thiram, tolclofos-methyl, tolylfluanid, triadimefon, toriadimenol, triazoxide, tricyclazole, tridemorph, triflumizole, triforine, triticonazole, validamycin, vinclozolin, zinc sulfate, zineb, ziram, and shiitake mushroom hyphae extract, etc.;
    Bactericides: streptomycin, tecloftalam, oxyterracycline, and oxolinic acid, etc.;
    Nematocides: aldoxycarb, cadusafos, fosthiazate, fosthietan, oxamyl, and fenamiphos, etc.;
    Acaricides: acequinocyl, amitraz, bifenazate, bromopropylate, chinomethionat, chlorobezilate, clofentezine, cyhexatine, dicofol, dienochlor, etoxazole, fenazaquin, fenbutatin oxide, fenpropathrin, fenproximate, halfenprox, hexythiazox, milbemectin, propargite, pyridaben, pyrimidifen, and tebufenpyrad, etc.;
    Insecticides: abamectin, acephate, acetamipirid, aldicarb, allethrin, azinphos-methyl, bendiocarb, benfuracarb, bensultap, bifenthrin, buprofezin, butocarboxim, carbaryl, carbofuran, carbosulfan, cartap, chlorfenapyr, chlorpyrifos, chlorfenvinphos, chlorfluazuron, clothianidin, chromafenozide, chlorpyrifos-methyl, cycloprothrin, cyfluthrin, beta-cyfluthrin, cypermethrin, cyromazine, cyhalothrin, lambda-cyhalothrin, deltamethrin, diafenthiuron, diazinon, diacloden, diflubenzuron, dimethylvinphos, diofenolan, disulfoton, dimethoate, emamectin-benzoate, EPN, esfenvalerate, ethiofencarb, ethiprole, etofenprox, etrimfos, fenitrothion, fenobucarb, fenoxycarb, fenpropathrin, fenvalerate, fipronil, fluacrypyrim, flucythrinate, flufenoxuron, flufenprox, tau-fluvalinate, fonophos, formetanate, formothion, furathiocarb, halofenozide, hexaflumuron, hydramethylnon, imidacloprid, isofenphos, indoxacarb, isoprocarb, isoxathion, lufenuron, malathion, metaldehyde, methamidophos, methidathion, methacrifos, metalcarb, methomyl, methoprene, methoxychlor, methoxyfenozide, monocrotophos, muscalure, nidinotefuran, nitenpyram, omethoate, oxydemeton-methyl, oxamyl, parathion, parathion-methyl, permethrin, phenthoate, phoxim, phorate, phosalone, phosmet, phosphamidon, pirimicarb, pirimiphos-methyl, profenofos, protrifenbute, pymetrozine, pyraclofos, pyriproxyfen, rotenone, sulprofos, silafluofen, spinosad, sulfotep, tebfenozide, teflubenzuron, tefluthorin, terbufos, tetrachlorvinphos, thiacloprid, thiocyclam, thiodicarb, thiamethoxam, thiofanox, thiometon, tolfenpyrad, tralomethrin, trichlorfon, triazuron, triflumuron, and vamidothion, etc.
    • EXAMPLES
  • Hereinafter, the present invention will be explained in more detail by specifically referring to Synthetic Examples and Test Examples of the compound of the present invention as working examples to which the present invention is not limited.
    • SYNTHETIC EXAMPLES Synthetic Example 1 Production of the Compound of the Present Invention by Use of L-COS (Parallel Liquid-Phase Synthesis System of MORITEX Corporation
  • In 15 bials of L-COS in which stirrers were placed, 1.5 mmol of each n-propylamine, i-propylamine, s-butylamine, t-butylamine, n-pentylamine, 2,2-dimethylpropylamine, n-hexylamine, cyclohexylamine, benzylamine, 4-trifluoromethylbenzylamine, 1-phenylethylamine, 2-phenylethylamine, 2-(4-phenoxyphenyl)ethylamine, 3-phenylpropylamine and trans-2-phenylcyclopropylamine was weighed, each bial was covered and placed in a reaction vessel of L-COS. With stirring at room temperature, in each bial, 5 ml of a solution of 4-[5-(3,4-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]benzoic acid in N,N-dimethylformamide-chlroform (1:3) (0.2 mmol/ml), 1 ml of a solution of 4-(dimethylamino) pyridine in chloroform (0.25 mmol/ml), and then 1.5 ml of a solution of 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride in chloroform (1.0 mmol/ml) were added in that order, and continued to stir at the same temperature for 16 hours. After the completion of the reaction, 3 ml of cold water was added in each bials, and the organic phases were collected, and subjected to purification with medium-pressure preparative liquid chromatography (Yamazen Corporation, medium pressure preparative system; YFLC-Wprep) that was eluted with ethyl acetate-hexane (1:3 to 1:1 gradient), and the aimed product was obtained as white to yellow solid. In addition, the product was confirmed with LC-MS (Waters LC-MS system, detector: ZMD, analysis condition: 254 nm, 80% CH3CN-20% H2O-0.1% HCOOH, ionization: positive electrospray).
    • 4-[5-(3,4-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-n-propylbenzoic acid amide; 0.26 g, [M++H]=444.94.
    • 4-[5-(3,4-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-i-propylbenzoic acid amide; 0.23 g, [M+H]=444.94.
    • N-s-butyl-4-[5-(3,4-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]benzoic acid amide; 0.20 g, [M++H]=458.93.
    • N-t-butyl-4-[5-(3,4-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]benzoic acid amide; 0.21 g, [M++H]=458.92.
    • 4-[5-(3,4-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-n-pentylbenzoic acid amide; 0.31 g, [M++H]=473.02.
    • 4-[5-(3,4-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(2,2-dimethylpropyl)benzoic acid amide; 0.27 g, [M++H]=472.94.
    • 4-[5-(3,4-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-n-hexylbenzoic acid amide; 0.26 g, [M++H]=486.96.
    • N-cyclohexyl-4-[5-(3,4-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]benzoic acid amide; 0.26 g, [M++H]=484.93.
    • N-benzyl-4-[5-(3,4-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]benzoic acid amide; 0.34 g, [M++H]=492.86.
    • 4-[5-(3,4-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(4-trifluoromethylbenzyl)benzoic acid amide; 0.34 g, [M++H]=560.97.
    • 4-[5-(3,4-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(1-phenylethyl)benzoic acid amide; 0.26 g, [M++H]=506.88.
    • 4-[5-(3,4-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(2-phenylethyl)benzoic acid amide; 0.37 g, [M++H]=507.01.
    • 4-[5-(3,4-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-[2-(4-phenoxyphenyl)ethyl]benzoic acid amide; 0.36 g, [M++H]=598.95.
    • 4-[5-(3,4-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(3-phenylpropyl)benzoic acid amide; 0.31 g, [M++H]=520.97.
    • 4-[5-(3,4-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(trans-2-phenylcyclopropyl)benzoic acid amide; 0.21 g, [M++H]=518.88.
    Synthetic Example 2 Production of the Compound of the Present Invention by Use of L-COS (Parallel Liquid-Phase Synthesis System of MORITEX Corporation)
  • Ten (10) bials of L-COS in which stirrers were placed were assigned a number of 1 to 10, respectively. 1.0 mmol of 3-chloro-4-fluorophenyl boric acid was weighed in the bials of Nos. 1 and 6, 1.0 mmol of 3,5-bis(trifluoromethyl)phenyl boric acid was weighed in the bials of Nos. 2 and 7, 1.0 mmol of 3-trifluoromethylphenyl boric acid was weighed in the bials of Nos. 3 and 8, 1.0 mmol of 3-trifluoromethoxyphenyl boric acid was weighed in the bials of Nos. 4 and 9, and 1.0 mmol of 2-naphthyl boric acid was weighed in the bials of Nos. 5 and 10, Then, 0.05 mmol of dichlorobis(triphenylphosphine) palladium (II) was added in each bial, the bial was filled with nitrogen and covered, and placed in a reaction vessel of L-COS. With stirring at room temperature, in each bial, 3 ml of a solution of 2-bromo-3,3,3-trifluoropropene in 1,2-dimethoxyethane (0.5 mmol/ml), 1.5 ml of water, and then 1 ml of a solution of triethylamine in 1,2-dimethoxyethane (6.0 mmol/ml) were added in that order, and stirred at 75° C. for 3.5 hours. Then, the bials were cooled to 0° C., 1.5 ml of a solution of N-benzyl-4-(chlrohydroxyiminomethyl)benzoic acid amide in 1,2-dimethoxyethane (0.7 mmol/ml) was added in the bials of Nos. 1 to 5, and 1.5 ml of a solution of 4-chlorohydroxyiminomethyl-N-(2,2,2-trifluoroethyl)benzoic acid amide in 1,2-dimethoxyethan (0.7 mmol/ml) was added in the bials of Nos. 6 to 10, and the bials were continued to stir at room temperature for 16 hours. After the completion of the reaction, the organic phase was collected, aqueous phase was extracted with 5 ml of chloroform, the chloroform was added to the organic phase, and the solvent was distilled off under reduced pressure. The residue was subjected to purification with medium-pressure preparative liquid chromatography (Yamazen Corporation, medium pressure preparative system; YFLC-Wprep) that was eluted with ethyl acetate-hexane (1:3 to 1:1 gradient), and the aimed product was obtained as white to yellow solid. In addition, the product was confirmed with LC-MS (Waters LC-MS system, detector: ZMD, analysis condition: 254 nm, 80% CH3CN-20% H2O-0.1% HCOOH, ionization: positive electrospray).
    • N-benzyl-4-[5-(3-chloro-4-fluorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]benzoic acid amide; 0.28 g, [M++H]=476.80.
    • N-benzyl-4-[5-[3,5-bis(trifluoromethyl)phenyl]-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]benzoic acid amide; 0.25 g, [M++H]=560.76.
    • N-benzyl-4-[5-(3-trifluoromethylphenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]benzoic acid amide; 0.26 g, [M++H]=492.82.
    • N-benzyl-4-[5-(3-trifluoromethoxyphenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]benzoic acid amide; 0.25 g, [M++H]=508.80.
    • N-benzyl-4-[5-(2-naphthyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]benzoic acid amide; 0.09 g, [M++H]=474.86.
    • 4-[5-(3-chloro-4-fluorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(2,2,2-trifluoroethyl)benzoic acid amide; 0.29 g, [M++H]=468.76.
    • 4-[5-[3,5-bis(trifluoromethyl)phenyl]-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(2,2,2-trifluoroethyl)benzoic acid amide; 0.29 g, [M++H]=552.72.
    • 4-[5-(3-trifluoromethylphenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(2,2,2-trifluoroethyl)benzoic acid amide; 0.18 g, [M++H]=484.78.
    • 4-[5-(3-trifluoromethoxyphenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(2,2,2-trifluoroethyl)benzoic acid amide; 0.27 g, [M++H]=500.76.
    • 4-[5-(2-naphthyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(2,2,2-trifluoroethyl)benzoic acid amide; 0.14 g, [M++H]=466.83.
    Synthetic Example 3 4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(2,2,2-trifluoroethyl)benzoic acid amide (Compound of the Present Invention No. 3-060) Step 1: Production of 3,5-dichloro-1-(1-trifluoromethylethenyl)benzene
  • In a solution of 25.0 g of 3,5-dichlorophenyl boric acid in 200 ml of tetrahydrofuran and 100 ml of water, 27.5 g of 2-bromo-3,3,3-trifluoropropene, 38.0 g of potassium carbonate and 1.84 g of dichlorobis(triphenylphosphine) palladium (II) were added, and stirred under reflux with heat for 3 hours. After the completion of the reaction and cooling to room temperature, 500 ml of ice water was added, and extracted with ethyl acetate (500 ml×1). The organic phase was washed with water, dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with hexane, and 25.7 g of the aimed product was obtained as colorless oily substance.
  • 1H NMR (CDCl3, Me4Si, 300 MHz) 7.41 (t, J=2.0 Hz, 1H), 7.3-7.35 (m, 2H), 6.05 (q, J=3.2 Hz, 1H), 5.82 (q, J=3.2 Hz, 1H).
    • Step 2: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]benzoic acid methyl ester
  • In a solution of 2.70 g of 4-(hydroxyiminomethyl)benzoic acid methyl ester in 15 ml of N,N-dimethylformamide, 2.04 g of N-chlorosuccinic acid imide was added, and stirred at 40° C. for 40 minutes. Then, the reaction mixture was cooled to 0° C., 3.40 g of 3,5-dichloro-1-(1-trifluoromethylethenyl)benzene and 1.72 g of triethylamine were added, continued to stir at room temperature for 18 hours. After the completion of the reaction, the reaction mixture was poured into 100 ml of ice water, extracted with ethyl acetate (50 ml×2), the organic phase was washed with water, dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residual solid was subjected to purification with medium-pressure preparative liquid chromatography (Yamazen Corporation, medium pressure preparative system; YFLC-Wprep) that was eluted with ethyl acetate-hexane (1:1 to 1:3 gradient), and 4.05 g of the aimed product was obtained as white crystal.
  • Melting point 94.0 to 96.0° C.
  • 1H NMR (CDCl3, Me4Si, 300 MHz) δ 8.10 (d, J=8.4 Hz, 2H), 7.74 (d, J=8.4 Hz, 2H), 7.43 (s, 2H), 7.26 (s, 1H), 4.12 (d, J=17.3 Hz, 1H), 3.94 (s, 3H), 3.74 (d, J=17.3 Hz, 1H).
    • Step 3: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]benzoic acid
  • In a solution of 3.99 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]benzoic acid methyl ester in 50 ml of methanol, a solution of 2.00 g of potassium hydroxide in 25 ml of water was added, stirred at room temperature for 3 days and then at 40° C. for 5 hours. After the completion of the reaction, the reaction mixture was cooled with ice, and poured in 200 ml of water, and adjusted to pH 1-2 with concentrated hydrochloric acid, and then extracted with ethyl acetate (50 ml×2), the organic phase was washed with water, dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 3.87 g of the aimed product as pale yellow crystal.
  • Melting point 237.0 to 240.0° C.
  • 1H NMR (CDCl3-DMSO-d6, Me4Si, 300 MHz) δ 8.09 (d, J=8.4 Hz, 2H), 7.76 (d, J=8.4 Hz, 2H), 7.54 (s, 2H), 7.44 (s, 1H), 4.18 (d, J=17.7 Hz, 1H), 3.86 (d, J=17.7 Hz, 1H).
    • Step 4: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(2,2,2-trifluoro ethyl)benzoic acid amide
  • In a suspension of 1.00 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]benzoic acid in 10 ml of benzene, 0.44 g of thionyl chloride and a catalytic amount (2 to 3 drops) of N,N-dimethylformamide were added, and stirred under reflux with heat for 2.5 hous. After the completion of the reaction, the solvent was distilled off under reduced pressure to obtain 1.81 g of crude 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]benzoic acid chloride as pale yellow oily substance. In a solution of 0.29 g of 2,2,2-trifluoroethylamine and 0.37 g of triethylamine in 20 ml of chloroform, 1.81 g of the crude 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]benzoic acid chloride dissolved in 10 ml of chloroform was added dropwise with cooling with ice and with stirring. After the completion of addition dropwise, the mixture was continued to stir at room temperature further for 30 minutes. After the completion of the reaction, the reaction mixture was poured in 100 ml of water, and extracted with chloroform (20 ml×3), the organic phase was washed with water, dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and passed through a glass filter packed with silica gel, and then the solvent was distilled off under reduced pressure. The residual solid was washed with hexane to obtain 1.05 g of the aimed product as white crystal.
  • Melting point 94.0 to 96.0° C.
  • 1H NMR (CDCl3, Me4Si, 300 MHz) δ 7.86 (d, J=8.4 Hz, 2H), 7.76 (d, J=8.4 Hz, 2H), 7.51 (s, 2H), 7.44 (s, 1H), 6.47 (t, J=6.3 Hz, 1H), 4.14 (qd, J=18.5, 6.3 Hz, 2H), 4.11 (d, J=17.4 Hz, 1H), 3.73 (d, J=17.4 Hz, 1H).
    • Synthetic Example 4 N-Benzyl-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-fluorobenzoic acid amide (Compound of the Present Invention No. 5-039) Step 1: Production of 3-(4-bromomethyl-3-fluorophenyl)-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole
  • In a solution of 1.50 g of 5-(3,5-dichlorophenyl)-3-(3-fluoro-4-methylphenyl)-5-trifluoromethyl-4,5-dihydroisoxazole synthesized from 3-fluoro-4-methylphenylaldoxime and 3,5-dichloro-1-(1-trifluoromethylethenyl)benzene similarly to Step 2 of Synthetic Example 3 in 50 ml of 1,2-dichloroethane, 0.68 g of N-bromosuccinic acid imide and a catalytic amount of azobisisobutyronitrile were added, and stirred under nitrogen atmosphere and under reflux with heat for 1 hour. After the completion of the reaction, the reaction mixture was left and cooled to room temperature, poured in 50 ml of water, extracted with chloroform (50 ml×1). The organic phase was dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain crude aimed product as pale yellow oily substance. The resulting product was used as such without purification for the next step.
  • 1H NMR (CDCl3, Me4Si, 400 MHz) δ 7.45-7.6 (m, 6H), 4.51 (s, 2H), 4.05 (d, J=17.2 Hz, 1H), 3.67 (d, J=17.2 Hz, 1H).
    • Step 2: Production of 3-(4-acetoxymethyl-3-fluorophenyl)-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole
  • In a solution of crude 3-(4-bromomethyl-3-fluorophenyl)-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole in 30 ml of acetic acid, 1.50 g of potassium acetate was added, and stirred under reflux with heat for 1.5 hour. After the completion of the reaction, the reaction mixture was left and cooled to room temperature, and neutralized by pouring in 100 ml of saturated sodium hydrogen carbonate aqueous solution. The organic phase was collected, dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 1.50 g of crude aimed product as pale yellow oily substance. The resulting product was used as such without purification for the next step.
  • 1H NMR (CDCl3, Me4Si, 400 MHz) δ 7.2-7.55 (m, 6H), 5.20 (s, 2H), 4.05 (d, J=17.2 Hz, 1H), 3.67 (d, J=17.2 Hz, 1H), 2.14 (s, 3H).
    • Step 3: Production of 5-(3,5-dichlorophenyl)-3-(3-fluoro-4-hydroxymethylphenyl)-5-trifluoromethyl-4,5-dihydroisoxazole
  • In a solution of 1.50 g of crude 3-(4-acetoxymethyl-3-fluorophenyl)-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole in 10 ml of ethanol, 2.00 g of sodium hydroxide dissolved in 20 ml of water was added, and stirred under reflux with heat for 4.5 hours. After the completion of the reaction, the reaction mixture was cooled with ice, and adjusted to pH 2-3 by carefully adding concentrated hydrochloric acid, and extracted with ethyl acetate (50 ml×1). The organic phase was dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (1:2) to obtain 0.95 g of the aimed product as pale yellow resinous substance.
  • 1H NMR (CDCl3, Me4Si, 400 MHz) δ 7.5-7.6 (m, 3H), 7.4-7.45 (m, 3H), 4.81 (s, 2H), 4.06 (d, J=17.2 Hz, 1H), 3.68 (d, J=17.2 Hz, 1H), 1.87 (bs, 1H).
    • Step 4: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-fluoro benzoic acid
  • In a solution of 0.95 g of 5-(3,5-dichlorophenyl)-3-(3-fluoro-4-hydroxymethylphenyl)-5-trifluoromethyl-4,5-dihydroisoxazole in 25 ml of acetone, Johnes' Reagent prepared from 1.50 g of chromic acid, 1.2 ml of concentrated sulfuric acid and 7 ml of water was added dropwise under cooling with ice and with stirring, after the completion of the addition dropwise, continued to stir at room temperature for further 1.5 hour. After the completion of the reaction, the reaction mixture was poured in 50 ml of water and extracted with diethyl ether (50 ml×1). The organic phase was dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residual solid was washed with hexane to obtain 0.67 g of the aimed product as beige crystal.
  • Melting point 172.0 to 174.0° C.
  • 1H NMR (CDCl3, Me4Si, 300 MHz) δ 8.05-8.15 (m, 1H), 7.45-7.55 (m, 5H), 4.08 (d, J=17.3 Hz, 1H), 3.71 (d, J=17.3 Hz, 1H).
    • Step 5: Production of N-benzyl-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-fluoro benzoic acid amide
  • In a solution of 0.15 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-fluoro benzoic acid in 10 ml of dichloromethane, 0.3 ml of oxalyl chloride and 2 drops of N,N-dimethylformamide were added at room temperature, and stirred at the same temperature for 10 minutes. After the completion of the reaction, the solvent was distilled off under reduced pressure, the remaining white solid was dissolved in 10 ml of chloroform, and 0.3 ml of benzylamine and then 0.3 ml of triethylamine were added under cooling with ice, after the completion of the addition, continued to stir at room temperature for further 20 minutes. After the completion of the reaction, 40 ml of water was poured in the reaction mixture, and extracted with ethyl acetate (50 ml×1). The organic phase was dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (1:2) to obtain 0.14 g of the aimed product as white crystal.
  • Melting point 172.0 to 176.0° C.
  • 1H NMR (CDCl3, Me4Si, 400 MHz) δ 8.20 (t, J=8.0 Hz, 1H), 7.25-7.55 (m, 10H), 7.05 (t, J=5.6 Hz, 1H), 4.68 (d, J=5.6 Hz, 2H), 4.07 (d, J=17.6 Hz, 1H), 3.70 (d, J=17.6 Hz, 1H).
    • Synthetic Example 5 4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-nitro-N-(2-pyridylmethyl)benzoic acid amide (Compound of the Present Invention No. 5-339) Step 1: Production of 4-bromo-3-nitrobenzaldoxime
  • In a solution of 5.0 g of 4-bromo-3-nitrobenzaldehyde in 50 ml of methanol, 3.6 ml of 50% hydroxyamine aqueous solution was added with stirring at room temperature, and continued to stir at the same temperature for 18 hours. After the completion of the reaction, 60 ml of water was added in the reaction mixture, and precipitated solid was filtered off, washed with water and then dried to obtain 5.0 g of the aimed product as yellow crystal.
  • 1H NMR (CDCl3-DMSO-d6, Me4Si, 400 MHz) δ 11.18 (s, 1H), 8.09 (s, 1H), 8.07 (d, J=2.0 Hz, 1H), 7.73 (d, J=8.4 Hz, 1H), 7.62 (dd, J=8.4, 2.0 Hz, 1H).
    • Step 2: Production of 3-(4-bromo-3-nitrophenyl)-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole
  • In a solution of 1.27 g of 4-bromo-3-nitrobenzaldoxime in 16 ml of N,N-dimethylformamide, 0.74 g of N-chlorosuccinic acid imide was added, and stirred at 35° C. for 90 minutes. Then, the reaction mixture was cooled with ice, 1.20 g of 3,5-dichloro-1-(1-trifluoromethylethenyl)benzene synthesized in Step 1 of Synthetic Example 3 and 0.60 g of triethylamine were added, continued to stir at room temperature for 18 hours. After the completion of the reaction, the reaction mixture was poured in 50 ml of ice water, extracted with ethyl acetate (50 ml×2), the organic phase was dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residual solid was subjected to purification with medium-pressure preparative liquid chromatography (Yamazen Corporation, medium pressure preparative system; YFLC-Wprep) that was eluted with ethyl acetate-hexane (1:2 to 1:4 gradient), and 1.10 g of the aimed product was obtained as yellow crystal.
  • Melting point 179.0 to 181.0° C.
  • 1H NMR (CDCl3, Me4Si, 400 MHz) δ 8.06 (d, J=2.0 Hz, 1H), 7.84 (d, J=8.4 Hz, 1H), 7.78 (dd, J=8.4, 2.0 Hz, 1H), 7.45-7.55 (m, 2H), 7.45 (t, J=1.8 Hz, 1H), 4.09 (d, J=17.2 Hz, 1H), 3.72 (d, J=17.4 Hz, 1H).
    • Step 3: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-nitrobenzoic acid ethyl ester
  • In a solution of 2.0 g of 3-(4-bromo-3-nitrophenyl)-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole in 30 ml of ethanol in an autoclave, 0.40 g of sodium acetate, 88.0 mg of 1,1′-bis(diphenylphosphino) ferrocene and 18.0 mg of palladium (II) acetate were added, and stirred under 0.9 MPa carbon monoxide atmosphere at 100° C. for 3 hours. After the completion of the reaction, the reaction mixture was left and cooled to room temperature, and the solvent was distilled off under reduced pressure, and the residue was dissolved in 100 ml of ethyl acetate, washed with water, dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The residual solid was subjected to purification with medium-pressure preparative liquid chromatography (Yamazen Corporation, medium pressure preparative system; YFLC-Wprep) that was eluted with ethyl acetate-hexane (1:2 to 1:4 gradient), and 0.66 g of the aimed product was obtained as pale yellow crystal.
  • Melting point 160.0 to 162.0° C.
  • 1H NMR (CDCl3, Me4Si, 400 MHz) δ 8.13 (d, J=1.6 Hz, 1H), 7.99 (dd, J=8.1, 1.6 Hz, 1H), 7.83 (d, J=8.1 Hz, 1H), 7.45-7.55 (m, 2H), 7.45 (t, J=1.8 Hz, 1H), 4.41 (q, J=7.1 Hz, 2H), 4.11 (d, J=17.2 Hz, 1H), 3.74 (d, J=17.8 Hz, 1H), 1.37 (t, J=7.1 Hz, 3H).
    • Step 4: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-nitro-N-(2-pyridylmethyl)benzoic acid amide
  • In a solution of 0.36 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-nitrobenzoic acid ethyl ester in 8 ml of ethanol, a solution of 0.40 g of potassium hydroxide in 2 ml of water was added, and stirred at room temperature for 3 hours. After the completion of the reaction, the reaction mixture was poured in 15 ml of water, adjusted to pH 4 with concentrated hydrochloric acid, then extracted with ethyl acetate (20 ml×2), the organic phase was washed with water, and then dehydrated with saturated sodium chloride aqueous solution and dried over over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure to obtain 0.40 g of crude 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-nitro benzoic acid as pale yellow oily substance. The substance was dissolved in 10 ml of chloroform, and 0.24 g of 2-picolylamine, 0.01 g of 4-(N,N-dimethylamino)pyridine and 0.35 g of 1-[3-(diethylamino)propyl]-3-ethylcarbodiimide hydrochloride were added, and stirred at room temperature for 18 hours. After the completion of the reaction, the solvent was distilled off under reduced pressure. The residue was subjected to purification with medium-pressure preparative liquid chromatography (Yamazen Corporation, medium pressure preparative system; YFLC-Wprep) that was eluted with ethyl acetate-hexane (1:1 to 1:0 gradient), and 0.14 g of the aimed product was obtained as colorless resinous substance.
  • 1H NMR (CDCl3-DMSO-d6, Me4Si, 300 MHz) δ 8.50 (d, J=4.8 Hz, 1H), 8.25 (d, J=1.7 Hz, 1H), 8.03 (dd, J=8.1, 1.6 Hz, 1H), 7.72 (td, J=7.7, 1.6 Hz, 1H), 7.68 (d, J=8.1 Hz, 1H), 7.51 (d, J=1.5 Hz, 2H), 7.45 (t, J=1.8 Hz, 1H), 7.43 (bs, 1H), 7.36 (d, J=7.9 Hz, 1H), 7.23 (dd, J=6.8, 5.3 Hz, 1H), 4.76 (d, J=4.8 Hz, 2H), 4.13 (d, J=17.4 Hz, 1H), 3.76 (d, J=17.4 Hz, 1H).
    • Synthetic Example 6 4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methoxy-N-(2,2,2-trifluoroethyl)benzoic acid amide (Compound of the Present Invention No. 5-317) Step 1: Production of 4-hydroxyiminomethyl-2-methoxyphenyl trifluoromethane sulfonate
  • In a solution of 3.0 g of 4-hydroxy-3-methoxybenzaldehyde and 2.4 g of triethylamine in 50 ml of dichloromethane, 5.8 g of trifluoromethane sulfonic acid anhydride was added dropwise under cooling with ice and with stirring, after the completion of the addition dropwise, continued to stir at the same temperature for 30 minutes. After the completion of the reaction, the reaction mixture was washed with 50 ml of water and then with 30 ml of saturated sodium hydrogen carbonate aqueous solution, and dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was dissolved in a mixture of 30 ml of ethanol and 15 ml of water, 1.4 g of hydroxyamine hydrochloride and 1.7 g of sodium acetate were added with stirring at room temperature, and continued to stir at the same temperature for further 1 hour. After the completion of the reaction, the solvent was distilled off under reduced pressure, extracted with ethyl acetate (40 ml×2), the organic phase was washed with water (30 ml×1), and then dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure to obtain 5.25 g of the aimed product as brown oily substance.
  • Refractive index nD 20.2° C.=1.5082
  • 1H NMR (CDCl3-DMSO-d6, Me4Si, 300 MHz) δ 8.47 (bs, 1H), 8.11 (s, 1H), 7.32 (s, 1H), 7.24 (d, J=8.1 Hz, 1H), 7.10 (d, J=8.1 Hz, 1H), 3.94 (s, 3H).
    • Step 2: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methoxyphenyl trifluoromethane sulfonate
  • In a solution of 2.0 g of 4-hydroxyiminomethyl-2-methoxyphenyl trifluoromethane sulfonate in 30 ml of N,N-dimethylformamide, 0.9 g of N-chlorosuccinic acid imide was added, and stirred at 40 to 50° C. for 30 minutes. Then, the reaction mixture was left and cooled to room temperature, 1.5 g of 3,5-dichloro-1-(1-trifluoromethylethenyl)benzene synthesized in Step 1 of Synthetic Example 3 and 0.7 g of triethylamine were added, and stirred at room temperature for 90 minutes. After the completion of the reaction, the reaction mixture was poured in 100 ml of ice water, extracted with ethyl acetate (50 ml×2), the organic phase was dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (1:7), and 1.4 g of the aimed product was obtained as colorless resinous substance.
  • 1H NMR (CDCl3, Me4Si, 300 MHz) δ 7.50 (s, 2H), 7.44 (s, 1H), 7.25-7.3 (m, 2H), 7.11 (d, J=8.4 Hz, 1H), 4.08 (d, J=17.1 Hz, 1H), 3.97 (s, 3H), 3.69 (d, J=17.1 Hz, 1H).
    • Step 3: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methoxy benzoic acid ethyl ester
  • In a solution of 1.50 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methoxyphen yl trifluoromethane sulfonate in 25 ml of ethanol in an autoclave, 0.27 g of sodium acetate, 31.0 mg of 1,1′-bis(diphenylphosphino) ferrocene and 7.0 mg of palladium (II) acetate were added, and stirred under 0.96 MPa carbon monoxide atmosphere at 100° C. for 2 hours. After the completion of the reaction, the reaction mixture was left and cooled to room temperature, and the reaction mixture was poured in 100 ml of ice water, extracted with ethyl acetate (40 ml×2). The organic phases together were dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (1:5), and 1.20 g of the aimed product was obtained as white crystal.
  • Melting point 142.0-144.0° C.
  • 1H NMR (CDCl3, Me4Si, 300 MHz) δ 7.82 (d, J=7.8 Hz, 1H), 7.51 (s, 2H), 7.4-7.45 (m, 2H), 7.10 (d, J=7.8 Hz, 1H), 4.37 (q, J=7.2 Hz, 2H), 4.10 (d, J=17.4 Hz, 1H), 3.95 (s, 3H), 3.71 (d, J=17.4 Hz, 1H), 1.39 (t, J=7.2 Hz, 3H).
    • Step 4: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methoxy benzoic acid
  • In a solution of 1.07 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methoxy benzoic acid ethyl ester in 30 ml of ethanol, a solution of 1.0 g of sodium hydroxide in 30 ml of water was added, stirred at 85° C. for 1 hour. After the completion of the reaction, the solvent was distilled off under reduced pressure. The residue was adjusted to pH 2 to 3 with concentrated hydrochloric acid, and extracted with ethyl acetate (30 ml×2). The organic phase was dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure to obtain 1.0 g of the aimed product as pale yellow resinous substance.
  • 1H NMR (CDCl3, Me4Si, 300 MHz) 10.67 (bs, 1H), 8.24 (d, J=7.8 Hz, 1H), 7.57 (s, 1H), 7.51 (s, 2H), 7.45 (s, 1H), 7.22 (d, J=7.8 Hz, 1H), 4.05-4.15 (m, 4H), 3.74 (d, J=17.4 Hz, 1H).
    • Step 5: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methoxy-N-(2,2,2-trifluoroethyl)benzoic acid amide
  • In a suspension of 0.25 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methoxy benzoic acid in 15 ml of dichloromethane, 0.09 g of oxalyl chloride and 1 drop of N,N-dimethylformamide were added, and stirred at room temperature for 1 hour. After the completion of the reaction, the solvent was distilled off under reduced pressure, the residue was dissolved in 15 ml of dichloromethane, and 0.09 g of triethylamine was added under cooling with ice, then 0.07 g of 2,2,2-trifluoroethylamine was added dropwise. After the completion of addition dropwise, the mixture was continued to stir at the same temperature for further 2 hours. Thereafter, the reaction mixture was diluted with 60 ml of chloroform, washed with 50 ml of water, then dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (1:2) to obtain 0.25 g of the aimed product as colorless resinous substance.
  • 1H NMR (CDCl3, Me4Si, 300 MHz) 8.2-8.3 (m, 2H), 7.51 (s, 3H), 7.43 (s, 1H), 7.17 (d, J=7.8 Hz, 1H), 4.05-4.2 (m, 3H), 4.05 (s, 3H), 3.74 (d, J=17.4 Hz, 1H).
    • Synthetic Example 7 4-[5-(4-Fluoro-3-methylphenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(2,2,2-trifluoroethyl)benzoic acid amide (Compound of the Present Invention No. 3-141) Step 1: Production of 4-formyl-N-(2,2,2-trifluoroethyl)benzoic acid amide
  • In a suspension of 1.00 g of 4-formyl benzoic acid in 15 ml of benzene, 0.87 g of thionyl chloride and 2 drops of N,N-dimethylformamide were added, and stirred under reflux with heat for 2 hours. After the completion of the reaction, the reaction mixture was left and cooled to room temperature, and the solvent was distilled off under reduced pressure to obtain 1.14 g of crude 4-formyl benzoic acid chloride as white crystal. In a solution of 0.66 g of 2,2,2-trifluoroethylamine and 0.81 g of triethylamine in 6 ml of chlororform, the solution of 1.14 g of the crude 4-formyl benzoic acid chloride in 6 ml of chloroform was added dropwise under cooling with ice and with stirring, after the completion of the addition dropwise, continued to stir at room temperature for further 18 hours. After the completion of the reaction, the reaction mixture was added in 30 ml of water, extracted with chloroform (20 ml×3). The organic phase was washed with water, dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, the residual solid was washed with hexane to obtain 1.32 g of the aimed product as white crystal.
  • Melting point 83.0 to 84.0° C.
  • 1H NMR (CDCl3, Me4Si, 400 MHz) 10.09 (s, 1H), 7.96 (bs, 4H), 6.80 (bs, 1H), 4.05-4.25 (m, 2H).
    • Step 2: Production of 4-hydroxyiminomethyl-N-(2,2,2-trifluoroethyl)benzoic acid amide
  • In a solution of 4.11 g of 4-formyl-N-(2,2,2-trifluoroethyl)benzoic acid amide in 30 ml of ethanol and 10 ml of water, 1.99 g of hydroxyamine hydrochloride and 2.51 g of anhydrous sodium acetate were added, stirred at room temperature for 3.5 hours. After the completion of the reaction, the reaction mixture was poured in 100 ml of water, and then extracted with ethyl acetate (30 ml×3), the organic phase was washed with 50 ml of saturated sodium hydrogen carbonate aqueous solution, then dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residual solid was washed with hexane to obtain 3.92 g of the aimed product as white crystal.
  • Melting point 153.0 to 154.0° C.
  • 1H NMR (CDCl3, Me4Si, 400 MHz) 10.89 (s, 1H), 8.08 (s, 1H), 8.03 (bs, 1H), 7.84 (d, J=8.2 Hz, 2H), 7.60 (d, J=8.2 Hz, 2H), 3.95-4.1 (m, 2H).
    • Step 3: Production of 4-chlorohydroxyiminomethyl-(2,2,2-trifluoroethyl)benzoic acid amide
  • In a solution of 3.80 g of 4-hydroxyiminomethyl-N-(2,2,2-trifluoroethyl)benzoic acid amide in 50 ml of tetrahydrofyran, 20 ml of 3N hydrochloric acid was added, 14 ml of 8% sodium hypochlorite aqueous solution was added dropwise with stirring under ice cooling over 10 minutes, after the completion of addition dropwise, continued to stir at the same temperature for further 15 minutes. After the completion of the reaction, the reaction mixture was poured in 200 ml of water, extracted with ethyl acetate (30 ml×3), the organic phase was dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resudual solid was washed with hexane to obtain 4.15 g of the product as white crystal.
  • Melting point 158.0 to 160.0° C.
  • 1H NMR (CDCl3, Me4Si, 400 MHz) 12.03 (s, 1H), 8.05 (t, J=6.0 Hz, 1H), 7.93 (bs, 4H), 3.95-4.15 (m, 2H).
    • Step 4: Production of 4-[5-(4-fluoro-3-methylphenyl)-5-trifluoromethyl-4,5-dihydrooxazol-3-yl]-N-(2,2,2-trifluoroethyl)benzoic acid amide
  • In a solution of 0.21 g of 4-fluoro-3-methylphenyl boric acid and 0.23 g of 2-bromo-3,3,3-trifluoropropene in 6 ml of 1,2-dimethoxyethane and 2 ml of water, 0.24 g of sodium carbonate and 0.05 g of dichlorobis(triphenylphosphine) palladium (II) were added, stirred at 75° C. for 3 hours. Then, the reaction mixture was left and cooled to room temperature, then a solution of 0.25 g of 4-chlorohydroxyiminomethyl-N-(2,2,2-trifluoroethyl)benzoic acid amide in 4 ml of 1,2-dimethoxyethane was added, continued to stir at the same temperature for further 18 hours. After the completion of the reaction, the reaction mixture was poured in 50 ml of water, extracted with ethyl acetate (10 ml×3), the organic phase was dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resudual solid was purified with silica gel column chromatography that was eluated with chloroform to obtain 0.24 g of the product as white crystal.
  • Melting point 151.0 to 152.0° C.
  • 1H NMR (CDCl3, Me4Si, 400 MHz) 7.86 (d, J=8.4 Hz, 2H), 7.76 (d, J=8.4 Hz, 2H), 7.35-7.5 (m, 2H), 7.0-7.15 (m, 1H), 6.39 (t, J=6.3 Hz, 1H), 4.05-4.25 (m, 2H), 4.09 (d, J=17.3 Hz, 1H), 3.74 (d, J=17.3 Hz, 1H), 2.32 (d, J=1.7 Hz, 3H).
    • Synthetic Example 8 4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-N-(2,2,2-trifluoroethyl)benzoic acid amide (Compound of the Present Invention No. 5-075) Step 1: Production of 4-bromo-2-methyl-N-(2,2,2-trifluoroethyl)benzoic acid amide
  • In a solution of 5.00 g of 4-bromo-2-methyl benzoic acid and 3.45 g of 2,2,2-trifluoroethylamine in 30 ml of N,N-dimethylformamide, 5.79 g of 1-[3-(diethylamino)propyl]-3-ethylcarbodiimide hydrochloride was added with stirring at room temperature, and stirred at the same temperature for 1.5 hour. After the completion of the reaction, 80 ml of water was added, and precipitated crystal was filtered off, washed with water and dried to obtain 4.00 g of the aimed product as white crystal.
  • Melting point 124.0 to 125.5° C.
  • 1H NMR (CDCl3, Me4Si, 400 MHz) 7.40 (s, 1H), 7.36 (d, J=8.4 Hz, 1H), 7.22 (d, J=8.4 Hz, 1H), 6.15 (bs, 1H), 4.0-4.15 (m, 2H), 2.39 (s, 3H).
    • Step 2: Production of 4-formyl-2-methyl-N-(2,2,2-trifluoroethyl)benzoic acid amide
  • In a solution of 1.00 g of 4-bromo-2-methyl-N-(2,2,2-trifluoroethyl)benzoic acid amide in 15 ml of tetrahydrofuran under nitrogen atmosphere, 4.7 ml of n-butyl lithium (1.58M hexane solution) was added dropwise at −70° C. with stirring, and then 0.4 ml of N,N-dimethylformamide were added dropwise. After stirring at the same temperature for 30 minutes, 10 ml of 1N hydrochloric acid and then 30 ml of water were added, and extracted with ethyl acetate (30 ml×2). The organic phase was dehydrated with saturated sodiun chloride aqueous solution and dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to obtain 0.80 g of the aimed product as pale yellow crystal.
  • Melting point 99.0 to 104.0° C.
  • 1H NMR (CDCl3, Me4Si, 400 MHz) 10.00 (s, 1H), 7.7-7.75 (m, 2H), 7.50 (d, J=7.5 Hz, 1H), 6.27 (bs, 1H), 4.05-4.2 (m, 2H), 2.49 (s, 3H).
    • Step 3: Production of 4-hydroxyiminomethyl-2-methyl-N-(2,2,2-trifluoroethyl)benzoic acid amide
  • In a solution of 0.8 g of 4-formyl-2-methyl-N-(2,2,2-trifluoroethyl)benzoic acid amide in 10 ml of ethanol and 5 ml of water, 0.3 g of hydroxyamine hydrochloride and 0.4 g of anhydrous sodium acetate were added with stirring at room temperature, and stirred at the same temperature for 30 minutes. After the completion of the reaction, the solvent was distilled off under reduced pressure, and precipitated crystal was filtered off, washed with water and dried to obtain 0.5 g of the aimed product as white crystal.
  • Melting point 190.5 to 194.0° C.
  • 1H NMR (CDCl3-DMSO-d6, Me4Si, 400 MHz) 10.98 (s, 1H), 8.43 (bs, 1H), 8.07 (s, 1H), 7.35-7.55 (m, 3H), 3.95-4.1 (m, 2H), 2.43 (s, 3H).
    • Step 4: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxasol-3-yl]-2-methyl-N-(2,2,2-trifluoroethyl)benzoic acid amide
  • In a solution of 0.40 g of 4-hydroxyiminomethyl-2-methyl-N-(2,2,2-trifluoroethyl)benzoic acid amide in 15 ml of N,N-dimethylformamide, 0.21 g of N-chlorosuccinc acid imide was added, and stirred at 50° C. for 30 minutes. Then, the reaction mixture was left and cooled to room temperature, 0.34 g of 3,5-dichloro-1-(1-trifluoromethylethenyl)benzene synthesized in Step 1 of Synthetic Example 3 and 0.16 g of triethylamine were added, and stirred at room temperature for 18 hours. After the completion of the reaction, the reaction mixture was poured in 50 ml of ice water, extracted with ethyl acetate (50 ml×1), the organic phase was dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (1:2), and 0.45 g of the aimed product was obtained as white crystal.
  • Melting point 155.5 to 157.0° C.
  • 1H NMR (CDCl3, Me4Si, 400 MHz) 7.4-7.55 (m, 6H), 6.13 (bs, 1H), 4.05-4.2 (m, 3H), 3.71 (d, J=17.4 Hz, 1H), 2.45 (s, 3H).
    • Synthetic Example 9 4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-N-(2-pyridylmethyl)benzoic acid amide (Compound of the Present Invention No. 5-234) Step 1: Production of 4-bromo-2-methyl-N-(2-pyridylmethyl)benzoic acid amide
  • In a solution of 3.0 g of 4-bromo-2-methyl benzoic acid in 30 ml of dichloromethane, 2.7 g of oxalyl chloride and 3 drops of N,N-dimethylformamide were added under cooling with ice with stirring, and stirred at room temperature for 1 hour. After the completion of the reaction, the solvent was distilled off under reduced pressure, the residue was dissolved in 30 ml of dichloromethane, 2.1 g of triethylamine and 2.0 g of 2-picolylamine were added under cooling with ice with stirring, and continued to stir at room temperature for 3 hours. After the completion of the reaction, 50 ml of water was added in the reaction mixture, extracted with chloroform (50 ml×2), the organic phase was washed with water, dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residual solid was washed with diisopropylether to obtain 3.7 g of the aimed product as yellow crystal.
  • Melting point 86.0 to 87.5° C.
  • 1H NMR (CDCl3, Me4Si, 300 MHz) 8.52 (d, J=4.8 Hz, 1H), 7.69 (td, J=7.8, 1.8 Hz, 1H), 7.15-7.4 (m, 6H), 4.73 (d, J=4.8 Hz, 2H), 2.45 (s, 3H).
    • Step 2: Production of 4-formyl-2-methyl-N-(2-pyridylmethyl)benzoic acid amide
  • In a solution of 2.0 g of 4-bromo-2-methyl-N-(2-pyridylmethyl)benzoic acid amide in 20 ml of N,N-dimethylformamide in an autoclave, 0.67 g of sodium formate and 0.10 g of dichlorobis(triphenylphosphine) palladium (II) were added, and stirred under 1.05 MPa carbon monoxide atmosphere at 110° C. for 3 hours. After the completion of the reaction, the reaction mixture was left and cooled to room temperature, and poured in 100 ml of water, and extracted with ethyl acetate (50 ml×2). The organic phases together were dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (9:1), and 0.50 g of the aimed product was obtained as pale yellow crystal.
  • Melting point 79.5 to 83.0° C.
  • 1H NMR (CDCl3, Me4Si, 300 MHz) 10.02 (s, 1H), 8.54 (d, J=5.1 Hz, 1H), 7.6-7.8 (m, 4H), 7.15-7.4 (m, 3H), 4.77 (d, J=4.8 Hz, 2H), 2.55 (s, 3H).
    • Step 3: Production of 4-hydroxyiminomethyl-2-methyl-N-(2-pyridylmethyl)benzoic acid amide
  • In a solution of 0.50 g of 4-formyl-2-methyl-N-(2-pyridylmethyl)benzoic acid amide in 10 ml of ethanol and 5 ml of water, 0.18 g of hydroxyamine hydrochloride was added with stirring at room temperature, and stirred at the same temperature for 12 hours. After the completion of the reaction, solid was filtered off, ethanol was distilled off under reduced pressure, and 30 ml of saturated sodium hydrogen carbonate aqueous solution was added in the remaining aqueous solution. The precipitated crystal was filtered off, washed with water and dried to obtain 0.45 g of the aimed product as pale yellow crystal.
  • Melting point 159.5 to 161.0° C.
  • 1H NMR (CDCl3-DMSO-d6, Me4Si, 300 MHz) 11.89 (bs, 1H), 8.56 (d, J=4.2 Hz, 1H), 8.03 (s, 1H), 7.90 (bs, 1H), 7.77 (t, J=7.8 Hz, 1H), 7.47 (d, J=7.5 Hz, 1H), 7.0-7.35 (m, 4H), 4.76 (d, J=6.0 Hz, 2H), 2.36 (s, 3H).
    • Step 4: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-N-(2-pyridylmethyl)benzoic acid amide
  • In a solution of 0.45 g of 4-hydroxyiminomethyl-2-methyl-N-(2-pyridylmethyl)benzoic acid amide in 10 ml of N,N-dimethylformamide, 0.25 g of N-chlorosuccinc acid imide was added, and stirred at 70° C. for 1 hour. Then, the reaction mixture was left and cooled to room temperature, 0.41 g of 3,5-dichloro-1-(1-trifluoromethylethenyl)benzene synthesized in Step 1 of Synthetic Example 3 and 0.25 g of potassium hydrogen carbonate were added, and stirred at room temperature for 3 hours. After the completion of the reaction, the reaction mixture was poured in 50 ml of ice water, extracted with ethyl acetate (60 ml×1), the organic phase was dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (3:1), and 0.30 g of the aimed product was obtained as white crystal.
  • Melting point 131.0 to 135.5° C.
  • 1H NMR (CDCl3, Me4Si, 300 MHz) 8.53 (d, J=5.0 Hz, 1H), 7.65-7.75 (m, 1H), 7.2-7.55 (m, 9H), 4.75 (d, J=4.9 Hz, 2H), 4.09 (d, J=17.3 Hz, 1H), 3.71 (d, J=17.3 Hz, 1H), 2.50 (s, 3H).
    • Synthetic Example 10 4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(2-pyridylmethyl)-2-trifluoromethyl benzoic acid amide (Compound of the Present Invention No. 5-315) Step 1: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-iodo benzoic acid methyl ester
  • In a solution of 0.60 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-iodo benzoic acid synthesized similarly to Steps 1 to 4 of Synthetic Example 4 in 10 ml of methanol, 2 drops of concentrated sulfuric acid was added, and stirred under reflux with heat for 20 hours. After the completion of the reaction, the solvent was distilled off under reduced pressure, the residue was neutralized with 10 ml of saturated sodium hydrogen carbonate aqueous solution, then extracted with ethyl acetate (10 ml×2). The organic phase was washed with water, dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (1:4), and 0.56 g of the aimed product was obtained as colorless oily substance.
  • 1H NMR (CDCl3, Me4Si, 400 MHz) 8.22 (d, J=1.5 Hz, 1H), 7.85 (d, J=8.2 Hz, 1H), 7.75-7.8 (m, 1H), 7.5-7.55 (m, 2H), 7.4-7.45 (m, 1H), 4.07 (d, J=17.7 Hz, 1H), 3.95 (s, 3H), 3.69 (d, J=17.2 Hz, 1H).
    • Step 2: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-trifluoromethyl benzoic acid methyl ester
  • In a solution of 0.51 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-iodo benzoic acid methyl ester in 5 ml of N,N-dimethylformamide, 0.18 g of copper (I) iodide, 0.06 g of potassium fluoride and 0.27 g of chlorodifluoro acetic acid methyl ester were added, and stirred at 120° C. for 5 hours. After the completion of the reaction, the reaction mixture was left and cooled to room temperature, 50 ml of water was added and extracted with ethyl acetate (50 ml×2). The organic phase was washed with water, dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (1:4), and 0.45 g of the aimed product was obtained as pale yellow oily substance.
  • 1H NMR (CDCl3, Me4Si, 400 MHz) 8.00 (d, J=1.1 Hz, 1H), 7.85-7.95 (m, 2H), 7.5-7.55 (m, 2H), 7.4-7.45 (m, 1H), 4.12 (d, J=7.1 Hz, 1H), 3.96 (s, 3H), 3.94 (d, J=7.8 Hz, 1H).
    • Step 3: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-trifluoromethyl benzoic acid
  • In a solution of 0.40 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-trifluoromethyl benzoic acid methyl ester in 5 ml of methanol, a solution of 0.10 g of sodium hydroxide in 2 ml of water was added, and stirred at room temperature for 18 hours. After the completion of the reaction, 10 ml of water was added in the reaction mixture, washed with 5 ml of toluene, aqueous phase was collected, adjusted to pH 1 to 2 with concentrated hydrochloric acid and then extracted with ethyl acetate (20 ml×2). The organic phase was washed with water, dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 0.34 g of the aimed product as pale yellow resinous substance. The resulting product was used as such without purification for the next step.
    • Step 4: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(2-pyridylmethyl)-2-trifluoromethyl benzoic acid amide
  • In a solution of 0.15 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-trifluoromethyl benzoic acid in 3 ml of dichloromethane, 0.06 g of oxalyl chloride and 1 drop of N,N-dimethylformamide were added under cooling with ice with stirring, and stirred at room temperature for 2 hours. After the completion of the reaction, the solvent was distilled off under reduced pressure, the residue was dissolved in 3 ml of dichloromethane, and a solution of 0.05 g of 2-picolylamine and 0.06 g of triethylamine in 1 ml of dichloromethane was added dropwise, after the completion of the addition dropwise, continued to stir at room temperature for 3 hours. After the completion of the reaction, 5 ml of water was added in the reaction mixture, extracted with chloroform (5 ml×2). The organic phase was washed with water, dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (1:3), and 0.05 g of the aimed product was obtained as white crystal.
  • Melting point 69.0 to 70.0° C.
  • 1H NMR (CDCl3, Me4Si, 400 MHz) 8.5-8.55 (m, 1H), 7.95 (bs, 1H), 7.91 (d, J=1.9 Hz, 1H), 7.65-7.8 (m, 2H), 7.5-7.55 (m, 2H), 7.35-7.45 (m, 3H), 7.26 (t, J=4.9 Hz, 1H), 4.77 (d, J=4.9 Hz, 2H), 4.11 (d, J=17.4 Hz, 1H), 3.73 (d, J=17.2 Hz, 1H).
    • Synthetic Example 11 4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-phenyl-N-(2-pyridylmethyl)benzoic acid amide (Compound of the Present Invention No. 5-344) Step 1: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-phenyl benzoic acid methyl ester
  • In a solution of 0.70 g of 2-bromo-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]benzoic acid methyl ester synthesized similarly to Step 1 of Synthetic Example 10 in 20 ml of tetrahydrofuran and 10 ml of water, 0.18 g of phenyl boric acid, 0.39 g of potassium carbonate and 0.05 g of dichlorobis(triphenylphosphine) palladium (II) were added, and stirred under reflux with heat for 1.5 hour. After the completion of the reaction, the solvent was distilled off under reduced pressure, the residue was poured in 30 ml of water, then extracted with ethyl acetate (50 ml×1). The organic phase was washed with water, dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethyl acetate, and 0.78 g of the aimed product was obtained as brown resinous substance.
  • 1H NMR (CDCl3, Me4Si, 400 MHz) 7.89 (d, J=8.4 Hz, 1H), 7.74 (dd, J=8.0, 1.8 Hz, 1H), 7.62 (d, J=1.4 Hz, 1H), 7.51 (d, J=1.8 Hz, 2H), 7.35-7.45 (m, 4H), 7.25-7.35 (m, 2H), 4.11 (d, J=16.8 Hz, 1H), 3.73 (d, J=16.8 Hz, 1H), 3.65 (s, 3H).
    • Step 2: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-phenyl benzoic acid
  • In a solution of 0.78 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-phenyl benzoic acid methyl ester in 15 ml of ethanol, a solution of 0.30 g of sodium hydroxide in 15 ml of water was added, and stirred at 60° C. for 3 hours. After the completion of the reaction, ethanol was distilled off under reduced pressure, adjusted to pH 1 to 2 with 12N hydrochloric acid, and then extracted with ethyl acetate (50 ml×1). The organic phase was washed with water, dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 0.70 g of the aimed product as brown glass substance. The resulting product was used as such without purification for the next step.
    • Step 3: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-phenyl-N-(2-pyridylmethyl)benzoic acid amide
  • In a solution of 0.3 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-phenyl benzoic acid in 10 ml of chloroform, 0.3 ml of oxalyl chloride and a catalytic amount (2 to 3 drops) of N,N-dimethylformamide were added with stirring at room temperature, and stirred at the same temperature for 10 minutes. After the completion of the reaction, the solvent was distilled off under reduced pressure, the residue was dissolved in 10 ml of chloroform, and under cooling with ice with stirring 0.3 ml of 2-picolylamine and then 0.3 ml of triethylamine were added, and continued to stir at room temperature for 20 minutes. After the completion of the reaction, the reaction mixture was poured in 40 ml of water, extracted with ethyl acetate (50 ml×1). The organic phase was washed with water, dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (2:1), and 0.2 g of the aimed product was obtained as white crystal.
  • Melting point 194.0 to 198.0° C.
  • 1H NMR (CDCl3, Me4Si, 400 MHz) 8.3-8.35 (m, 1H), 7.25-7.8 (m, 12H), 7.1-7.15 (m, 1H), 7.40 (d, J=7.8 Hz, 1H), 6.65-6.7 (m, 1H), 4.47 (d, J=5.0 Hz, 2H), 4.12 (d, J=17.0 Hz, 1H), 3.74 (d, J=17.0 Hz, 1H).
    • Synthetic Example 12 2-Amino-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(2,2,2-trifluoroethyl)benzoic acid amide (Compound of the Present Invention No. 5-329) Step 1: Production of 2-amino-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]benzoic acid ethyl ester
  • In a solution of 0.60 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-nitro benzoic acid ethyl ester synthesized in Steps 1 to 3 of Synthetic Example 5 in 6 ml of ethyl acetate, 2.0 ml of water, 0.6 ml of acetic acid and 0.46 g of reduced iron were added, and stirred at 75° C. for 2 hours. After the completion of the reaction, the organic phase was collected, and the aqueous phase was extracted with ethyl acetate (10 ml×2). The organic phases together were washed with water, dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 0.60 g of crude aimed product as brown oily substance. The resulting product was used as such without purification for the next step.
    • Step 2: Production of 2-amino-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]benzoic acid
  • In a solution of 0.6 g of crude 2-amino-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]benzoic acid ethyl ester in 7 ml of ethanol, a solution of 0.5 g of potassium hydroxide in 2.0 ml of water was added, and stirred at room temperature for 18 hours. After the completion of the reaction, 20 ml of ice water was added in the reaction mixture, adjusted to pH 2 to 3 with concentrated hydrochloric acid, and then extracted with ethyl acetate (20 ml×2). The organic phase was washed with water, dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 0.6 g of crude aimed product as yellow oily substance. The resulting product was used as such without purification for the next step.
    • Step 3: Production of 2-amino-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(2,2,2-trifluoroethyl)benzoic acid amide
  • In a solution of 0.60 g of crude 2-amino-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]benzoic acid in 6 ml of chloroform, 0.20 g of 2,2,2-trifluoroethylamine, 0.02 g of 4-(N,N-dimethylamino) pyridine and 0.33 g of 1-[3-(diethylamino)propyl]-3-ethylcarbodiimide hydrochloride were added, and stirred at room temperature for 20 hours. After the completion of the reaction, the reaction mixture was subjected to purification with medium-pressure preparative liquid chromatography (Yamazen Corporation, medium pressure preparative system; YFLC-Wprep) that was eluted with ethyl acetate-hexane (1:4), and 0.14 g of the aimed product was obtained as pale yellow crystal.
  • Melting point 78.0 to 79.0° C.
  • 1H NMR (CDCl3, Me4Si, 400 MHz) 7.50 (d, J=1.8 Hz, 2H), 7.43 (t, J=1.8 Hz, 1H), 7.39 (d, J=8.6 Hz, 1H), 6.95-7.0 (m, 2H), 6.29 (t, J=7.0 Hz, 1H), 5.68 (bs, 2H), 4.05-4.15 (m, 2H), 4.04 (d, J=17.2 Hz, 1H), 3.67 (d, J=17.2 Hz, 1H).
    • Synthetic Example 13 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylthio-N-(2-pyridylmethyl)benzoic acid amide (Compound of the Present Invention No. 5-323)
  • In a solution of 0.92 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-fluoro-N-(2-pyridylmethyl)benzoic acid amide (Compound of the present invention No. 5-041) synthesized similarly to Synthetic Example 4 in 12 ml of dimethylsulfoxide, 0.12 g of sodium methane thiolate was added with stirring at room temperature, and stirred at 100° C. for 90 minutes. After the completion of the reaction, the reaction mixture was poured in 30 ml of water, and extracted with ethyl acetate (20 ml×3). The organic phase was washed with 30 ml of water, dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with chloroform, and 0.89 g of the aimed product was obtained as colorless oily substance.
  • 1H NMR (CDCl3, Me4Si, 300 MHz) 8.51 (d, J=4.8 Hz, 1H), 7.6-7.75 (m, 4H), 7.52 (bs, 2H), 7.42 (bs, 1H), 7.37 (bs, 1H), 7.34 (bs, 1H), 7.20 (dd, J=6.9, 1.8 Hz, 1H), 4.74 (d, J=4.8 Hz, 2H), 4.10 (d, J=17.1 Hz, 1H), 3.75 (d, J=17.1 Hz, 1H), 2.47 (s, 3H).
    • Synthetic Example 14 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylsulfinyl-N-(2,2,2-trifluoroethyl)benzoic acid amide (Compound of the Present Invention No. 5-324)
  • In a solution of 0.38 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylthio-N-(2,2,2-trifluoroethyl)benzoic acid amide (Compound of the present invention No. 5-322) synthesized similarly to Synthetic Example 13 in 6 ml of 1,2-dichloroethane, 0.10 g of N-chlorosuccinic acid imide was added with stirring at room temperature, and stirred at the same temperature for 11 hours. After the completion of the reaction, the reaction mixture was poured in 30 ml of water, and extracted with ethyl acetate (20 ml×3). The organic phase was washed with 30 ml of saturated sodium hydrogen carbonate, dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (1:2), and 0.17 g of the aimed product was obtained as colorless oily substance.
  • 1H NMR (CDCl3, Me4Si, 300 MHz) 8.16 (t, J=8.1 Hz, 1H), 7.6-7.8 (m, 3H), 7.55 (d, J=8.1 Hz, 1H), 7.51 (d, J=8.1 Hz, 1H), 7.15 and 7.11 (t, J=6.3 Hz, 1H), 4.18 (qd, J=18.5, 6.3 Hz, 2H), 4.15 (d, J=17.7 Hz, 1H), 3.80 (d, J=17.7 Hz, 1H), 2.79 and 2.78 (s, 3H).
    • Synthetic Example 15 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylsulfonyl-N-(2,2,2-trifluoroethyl)benzoic acid amide (Compound of the Present Invention No. 5-326)
  • In a solution of 0.25 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylthio-N-(2,2,2-trifluoroethyl)benzoic acid amide (Compound of the present invention No. 5-322) synthesized similarly to Synthetic Example 13 in 6 ml of dichloromethane, 0.17 g of 3-chloroperbenzoic acid was added with stirring at room temperature, and stirred at the same temperature for 3 days. After the completion of the reaction, the reaction mixture was poured in 30 ml of sodium thiosulfate aqueous solution, and extracted with chloroform (10 ml×3). The organic phase was dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with chloroform, and 0.20 g of the aimed product was obtained as colorless oily substance.
  • 1H NMR (CDCl3, Me4Si, 300 MHz) 8.16 (t, J=8.4 Hz, 1H), 8.05 (bs, 1H), 8.00 (s, 1H), 7.92 (s, 1H), 7.55 (d, J=8.4 Hz, 1H), 7.52 (d, J=8.4 Hz, 1H), 7.06 and 7.02 (t, J=6.4 Hz, 1H), 4.17 (d, J=17.4 Hz, 1H), 4.16 (qd, J=18.5, 6.3 Hz, 2H), 3.79 (d, J=17.4 Hz, 1H), 2.12 (s, 3H).
    • Synthetic Example 16 2-Cyano-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(2-pyridylmethyl)benzoic acid amide (Compound of the Present Invention No. 5-341)
  • In a solution of 0.19 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-iodo-N-(2-pyridylmethyl)benzoic acid amide (Compound of the present invention No. 5-065) synthesized similarly to Synthetic Example 4 in 10 ml of dimethylacetamide, 36.0 mg of zinc cyanide, 4.8 mg of zinc, 11.0 mg of tris(dibenzylideneacetone) dipalladium and 13.5 mg of 1,1′-bis(diphenylphosphino)ferrocene were added, and stirred under nitrogen atmosphere at 80 to 120° C. for 5 hours. After the completion of the reaction, 30 ml of ammonia water and 20 ml of water were added in the reaction mixture, and extracted with ethyl acetate (50 ml×1). The organic phase was washed with 30 ml of water, dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethylacetate-hexane (2:1), and 0.05 g of the aimed product was obtained as brown resinous substance.
  • 1H NMR (CDCl3, Me4Si, 400 MHz) 8.5-8.6 (m, 1H), 8.12 (bs, 1H), 7.9-8.0 (m, 2H), 7.15-7.7 (m, 7H), 5.13 (bs, 2H), 4.14 (d, J=17.4 Hz, 1H), 3.78 (d, J=17.4 Hz, 1H).
    • Synthetic Example 17 2-Acetylamino-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(2,2,2-trifluoroethyl)benzoic acid amide (Compound of the Present Invention No. 5-333)
  • In a solution of 0.05 g of 2-amino-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(2,2,2-trifluoroethyl)benzoic acid amide (Compound of the present invention No. 5-329) synthesized in Synthetic Example 12 and 0.15 ml of triethylamine in 2 ml of chloroform, 0.10 ml of acetic anhydride was added under cooling with ice with stirring, and stirred at room temperature for 20 hours. After the completion of the reaction, the reaction mixture was subjected to purification with medium-pressure preparative liquid chromatography (Yamazen Corporation, medium pressure preparative system; YFLC-Wprep) that was eluted with ethyl acetate-hexane (1:8 to 1:1 gradient), and 0.045 g of the aimed product was obtained as pale yellow resinous substance.
  • 1H NMR (CDCl3, Me4Si, 400 MHz) 10.90 (bs, 1H), 8.77 (d, J=1.3 Hz, 1H), 7.57 (dd, J=8.4, 1.5 Hz, 1H), 7.53 (d, J=8.4 Hz, 1H), 7.50 (d, J=1.7 Hz, 2H), 7.45 (t, J=1.8 Hz, 1H), 6.82 (bs, 1H), 4.1-4.2 (m, 2H), 4.11 (d, J=17.0 Hz, 1H), 3.73 (d, J=17.0 Hz, 1H), 2.22 (s, 3H).
    • Synthetic Example 18 4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylamino-N-(2,2,2-trifluoroethyl)benzoic acid amide (Compound of the Present Invention No. 5-331) and 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-dimethylamino-N-(2,2,2-trifluoroethyl)benzoic acid amide (Compound of the Present Invention No. 5-334)
  • In a solution of 0.25 g of 2-amino-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(2,2,2-trifluoroethyl)benzoic acid amide (Compound of the Present Invention No. 5-329) synthesized in Synthetic Example 12 and 0.06 g of 36% formaldehyde aqueous solution in 7 ml of 1,2-dichloroethane, 1.00 g of sodium triacetoxy borohydride was added with stirring at room temperature in three portions at 1 hour-interval, and continued to stir at the same temperature for further 2 hours. After the completion of the reaction, the reaction mixture was poured to 5 ml of ice water, the organic phase was collected, and the solvent was distilled under reduced pressure. The residue was subjected to purification with medium-pressure preparative liquid chromatography (Yamazen Corporation, medium pressure preparative system; YFLC-Wprep) that was eluted with ethyl acetate-hexane (0:1 to 1:3 gradient), and 0.13 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylamino-N-(2,2,2-trifluoroethyl)benzoic acid amide was obtained as pale yellow crystal, and 0.13 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-dimethylamino-N-(2,2,2-trifluoroethyl)benzoic acid amide was obtained as pale yellow resinous substance.
    • 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylamino-N-(2,2,2-trifluoroethyl)benzoic acid amide;
  • Melting point 156.0 to 158.0° C.
  • 1H NMR (CDCl3, Me4Si, 400 MHz) 7.57 (bs, 1H), 7.52 (d, J=1.6 Hz, 2H), 7.43 (t, J=1.8 Hz, 1H), 7.38 (d, J=8.2 Hz, 1H), 6.92 (d, J=1.6 Hz, 1H), 6.84 (dd, J=8.2, 1.6 Hz, 1H), 6.31 (t, J=6.4 Hz, 1H), 4.0-4.15 (m, 2H), 4.08 (d, J=17.2 Hz, 1H), 3.70 (d, J=17.2 Hz, 1H), 2.91 (s, 3H).
    • 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-dimethylamino-N-(2,2,2-trifluoroethyl)benzoic acid amide;
  • 1H NMR (CDCl3, Me4Si, 400 MHz) 10.29 (t, J=6.2 Hz, 1H), 8.22 (d, J=8.1 Hz, 1H), 7.73 (d, J=1.7 Hz, 1H), 7.52 (d, J=1.7 Hz, 2H), 7.44 (t, J=1.8 Hz, 1H), 7.33 (dd, J=8.1, 1.6 Hz, 1H), 4.13 (qd, J=9.2, 6.2 Hz, 2H), 4.10 (d, J=17.2 Hz, 1H), 3.72 (d, J=17.2 Hz, 1H), 2.78 (s, 6H).
    • Synthetic Example 19 4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(2-methoxyiminoethyl)-2-methyl benzoic acid amide (Compound of the Present Invention No. 5-113)
  • In a solution of 152 mg of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(2,2-dimethoxyethyl)-2-methyl benzoic acid amide (Compound of the present invention No. 5-083) synthesized similarly to Synthetic Example 5 in 14 ml of methanol-water (6:1) mixed solvent, 38 mg of methoxyamine hydrochloride was added, and stirred under reflux with heat for 8 hours. After the completion of the reaction, the reaction mixture was left and cooled to room temperature, diluted by adding 80 ml of ethyl acetate, washed with water (30 ml×2), and dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethylacetate-hexane (1:1), and 102 mg of the aimed product was obtained as colorless resinous substance.
  • 1H NMR (CDCl3, Me4Si, 300 MHz) 7.45-7.55 (m, 6H), 7.45-7.55 and 6.83 (t, J=4.5 Hz, 1H), 7.4-7.45 (m, 1H), 6.28 and 6.16 (t, J=4.7 Hz, 1H), 4.27 and 4.22 (t, J=4.7 Hz, 2H), 4.08 (d, J=17.1 Hz, 1H), 3.92 and 3.85 (s, 3H), 3.70 (d, J=17.4 Hz, 1H), 2.50 and 2.48 (s, 3H).
    • Synthetic Example 20
  • N-[4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylbenzoyl]glycine (Compound of the Present Invention No. 5-127)
  • In a solution of 2.6 g of methyl N-[4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylbenz oyl]glycine (Compound of the present invention No. 5-128) synthesized similarly to Synthetic Example 5 in 10 ml of methanol, a solution of 1.0 g of potassium hydroxide in 10 ml of water was added with stirring at room temperature, and stirred at the same temperature for further 1 hour. After the completion of the reaction, 10 ml of 12N hydrochloric acid was added and extracted with ethyl acetate (50 ml×1), the organic phase was dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 2.4 g of the aimed product as pale yellow resinous resinous substance.
  • 1H NMR (CDCl3, Me4Si, 300 MHz) 7.4-7.55 (m, 6H), 6.35-6.85 (m, 2H), 4.23 (d, J=5.7 Hz, 2H), 4.08 (d, J=17.1 Hz, 1H), 3.71 (d, J=17.1 Hz, 1H), 2.44 (s, 3H).
    • Synthetic Example 21 4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-N—[N-(2,2,2-trifluoroethyl) carbamoylmethyl]benzoic acid amide (Compound of the Present Invention No. 5-151)
  • In a solution of 1.00 g of N-[4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylbenz oyl]glycine (Compound of the present invention No. 5-127) synthesized in Synthetic Example 20 in 30 ml of dichloromethane, 0.65 g of 1-[3-(diethylamino)propyl]-3-ethylcarbodiimide hydrochloride was added, and stirred at room temperature for 15 minutes, then 0.40 g of 2,2,2-trifluoroethylamine and 0.40 g of 4-(N,N-dimethylamino)pyridine were added and stirred at the same temperature for further 2 hours. After the completion of the reaction, the solvent was distilled off under reduced pressure, the residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (1:3), and then crystallized from hexane to obtain 0.48 g of the aimed product as white crystal.
  • Melting point 173.5 to 175.5° C.
  • 1H NMR (CDCl3, Me4Si, 300 MHz) 7.35-7.55 (m, 7H), 7.03 (t, J=5.1 Hz, 1H), 4.21 (d, J=5.1 Hz, 2H), 4.09 (d, J=17.4 Hz, 1H), 3.85-4.0 (m, 2H), 3.71 (d, J=17.4 Hz, 1H), 2.43 (s, 3H).
    • Synthetic Example 22 4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-N-(N-phenylcarbamoylmethyl)benzoic acid amide (Compound of the present invention No. 5-169)
  • In a solution of 0.40 g of Ni-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylbenzoyl]glycine (Compound of the present invention No. 5-127) synthesized in Synthetic Example 20 and 0.08 g of pyridine in 10 ml of dichloromethane, 0.12 g of pivaloyl chloride was added, and stirred at room temperature for 2 hours, then 0.50 g of aniline and 3 ml of triethylamine were added and stirred at the same temperature for further 1 hour. After the completion of the reaction, 20 ml of water was added in the reaction mixture and extracted with ethyl acetate (50 ml×1), the organic phase was dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (2:1) to obtain 0.12 g of the aimed product as white crystal.
  • Melting point 181.0 to 183.0° C.
  • 1H NMR (CDCl3, Me4Si, 300 MHz) 8.54 (bs, 1H), 7.5-7.55 (m, 7H), 7.44 (t, J=2.0 Hz, 1H), 7.31 (t, J=8.0 Hz, 2H), 7.1-7.2 (m, 1H), 6.95 (bs, 1H), 4.34 (d, J=5.0 Hz, 2H), 4.19 (d, J=17.2 Hz, 1H), 3.70 (d, J=17.2 Hz, 1H), 2.49 (s, 3H).
    • Synthetic Example 23 4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-N-met hyl-N-(2-pyridylmethyl)benzoic acid amide (Compound of the Present Invention No. 6-020)
  • In a solution of 0.35 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-N-(2-pyridylmethyl)benzoic acid amide (Compound of the present invention No. 5-234) synthesized similarly to Synthetic Example 5 in 20 ml of N,N-dimethylformamide, 0.04 g of 55% oily sodium hydride was added under cooling with ice with stirring, and stirred at the same temperature for 30 minutes. Then, 0.12 g of methyl iodide was added and thereafter the temperature was raised to room temperature, and continued to stir at the same temperature for further 2 hours. After the completion of the reaction, the reaction mixture was diluted with 80 ml of ethyl acetate, washed with water (50 ml×2), dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with high performance liquid chromatography that was eluated with acetonitrile-water (85:15) to obtain 0.25 g of the aimed product as colorless resinous substance.
  • 1H NMR (CDCl3, Me4Si, 300 MHz) 8.5-8.6 (m, 1H), 7.6-7.75 (m, 1H), 7.05-7.55 (m, 8H), 4.43 and 4.89 (bs, 2H), 4.06 and 4.09 (d, J=17.4 and 17.1 Hz, 1H), 3.68 and 3.71 (d, J=17.4 and 17.1 Hz, 1H), 2.85 and 3.13 (s, 3H), 2.35 and 2.38 (s, 3H).
    • Synthetic Example 24 7-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-1-methyl-3-(2-pyridylmethyl)-1,2,3,4-tetrahydroquinazolin-4-one (Compound of the Present Invention No. 6-071)
  • In a solution of 0.06 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylamino-N-(2-pyridylmethyl)benzoic acid amide (Compound of the present invention No. 5-332) synthesized similarly to Synthetic Example 18 in 5 ml of dichloromethane, 0.03 g of chloromethylether was added, and stirred at the same temperature for 15 hours After the completion of the reaction, the solvent was distilled off under reduced pressure, and the residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (3:1) to obtain 0.04 g of the aimed product as colorless oily substance.
  • 1H NMR (CDCl3, Me4Si, 300 MHz) 8.5-8.6 (m, 1H), 8.04 (d, J=7.8 Hz, 1H), 7.6-7.75 (m, 1H), 7.4-7.55 (m, 4H), 7.15-7.3 (m, 1H), 7.10 (bs, 1H), 6.95-7.05 (m, 1H), 4.86 (s, 2H), 4.06 (s, 2H), 4.09 (d, J=17.4 Hz, 1H), 3.70 (d, J=17.4 Hz, 1H), 2.90 (s, 3H).
    • Synthetic Example 25 4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-N-(2,2,2-trifluoroethyl)benzoic acid thioamide (Compound of the Present Invention No. 7-007)
  • A solution of 0.50 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-N-(2,2,2-trifluoroethyl)benzoic acid amide (Compound of the present invention No. 5-075) synthesized in Synthetic Example 8 and 0.41 g of Lawesson's Reagent (2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetan-2,4-disulfide) in 15 ml of toluene was stirred under reflux with heat for 20 hours. After the completion of the reaction, the reaction mixture was left and cooled to room temperature, and the reaction mixture was diluted with 60 ml of ethyl acetate, washed with water (50 ml×1), then dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (3:1) to obtain 0.40 g of the aimed product as yellow resinous substance.
  • 1H NMR (CDCl3, Me4Si, 300 MHz) 7.2-7.5 (m, 7H), 4.55-4.7 (m, 2H), 4.06 (d, J=17.1 Hz, 1H), 3.68 (d, J=17.1 Hz, 1H), 2.38 (s, 3H).
    • Synthetic Example 26 4-[5-(3-Bromodifluoromethoxyphenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-N-(2,2,2-trifluoroethyl)benzoic acid amide (Compound of the Present Invention No. 5-014) Step 1: Production of 3-bromodifluoromethoxy-1-iodobenzene
  • In a suspension of 0.87 g of 55% oily sodium hydride in 20 ml of N,N-dimethylformamide, a solution of 4.00 g of 3-iodophenol in 10 ml of N,N-dimethylformamide was added dropwise with stirring under ice cooling, after the completion of the addition dropwise, stirred at room temperature for 30 minutes. The reaction mixture was added dropwise in a solution of 11.40 g of dibromodifluoromethane in 20 ml of N,N-dimethylformamide under cooling with ice with stirring, after the completion of the addition dropwise, continued to stir at room temperature for 2 hours. After the completion of the reaction, 50 ml of water was added in the reaction mixture, extracted with ethyl acetate (100 ml×1), the organic phase was washed with water, then dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with hexane to obtain 2.10 g of the aimed product as colorless oily substance.
  • 1H NMR (CDCl3, Me4Si, 300 MHz) 7.65-7.7 (m, 1H), 7.55-7.65 (m, 1H), 7.2-7.3 (m, 1H), 7.15 (t, J=9.0 Hz, 1H).
    • Step 2: Production of 3-bromodifluoromethoxy-1-(1-trifluoromethylethenyl)benzene
  • In 10 ml of a solution of 1-trifluoromethylethenyl zinc bromide prepared according to the method described in documents in 1M tetrahydrofuran, 1.0 g of 3-bromodifluoromethoxy-1-iodobenzene and 0.05 g of dichlorobis(triphenylphosphine) palladium (II) were added, and stirred under reflux with heat for 2 hours. After the completion of the reaction, the reaction mixture was poured in 20 ml of diluted hydrochloric acid, extracted with ethyl acetate (50 ml×1). The organic phase was dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was dissolved in hexane, and high polar impurities were excluded by treating with silica gel to obtain 0.77 g of crude aimed product as colorless oily substance. The resulting product was used as such without purification for the next step.
    • Step 3: Production of 4-[5-(3-bromodifluoromethoxyphenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-N-(2,2,2-trifluoroethyl)benzoic acid amide
  • In a solution of 0.3 g of 4-chlorohydroxyiminomethyl-2-methyl-N-(2,2,2-trifluoroethyl)benzoic acid amide synthesized similarly to Steps 1 to 3 of Synthetic Example 7 and 0.2 g of crude 3-bromodifluoromethoxy-1-(1-trifluoromethylethenyl)benzene in 10 ml of 1,2-dimethoxyethane, 0.4 g of potassium hydrogen carbonate was added, and stirred at room temperature for 18 hours. After the completion of the reaction, the reaction mixture was poured in 20 ml of water, extracted with ethyl acetate (50 ml×1). The organic phase was dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (1:1) to obtain 0.29 g of the aimed product as colorless glass substance.
  • 1H NMR (CDCl3, Me4Si, 400 MHz) 7.5-7.6 (m, 5H), 7.41 (d, J=7.8 Hz, 1H), 7.3-7.5 (m, 1H), 6.16 (t, J=6.6 Hz, 1H), 4.05-4.15 (m, 3H), 3.74 (d, J=17.2 Hz, 1H), 2.45 (s, 3H).
    • Synthetic Example 27 4-[5-Chlorodifluoromethyl-5-(3,5-dichlorophenyl)-4,5-dihydroisoxazol-3-yl]-2-methyl-N-(2,2,2-trifluoroethyl)benzoic acid amide (Compound of the Present Invention No. 5-355) Step 1: Production of 2,3′,5′-trichloro-2,2-difluoroacetophenone
  • In a solution of 5.0 g of 3,5-dichloro-1-iodobenzene in 50 ml of t-butylmethylether, 12.2 ml of n-butyl lithium (1.58M hexane solution) was added dropwise at −78° C. with stirring, after the completion of the addition dropwise, stirred at the same temperature for 30 minutes. 6.6 g of chlorodifluoroacetic acid methyl ester was added dropwise at −78° C. with stirring in the reaction mixture, after the completion of the addition dropwise, continued to stir at 0° C. for further 30 minutes. After the completion of the reaction, the reaction mixture was poured in 100 ml of saturated ammonium chloride aqueous solution, extracted with ethyl acetate (100 ml×1). The organic phase was dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure to obtain 4.6 g of crude aimed product as pale yellow oily substance. The resulting product was used as such without purification for the next step.
  • 1H NMR (CDCl3, Me4Si, 300 MHz) 7.97 (s, 2H), 7.68 (s, 1H).
    • Step 2: Production of 3,5-dichloro-1-[1-(chlorodifluorofluoromethyl)ethenyl]benzene
  • in a solution of 2.89 g of methyltriphenylphosphonium bromide in 15 ml of tetrahydrofuran, 0.91 g of potassium t-butoxide was added, and stirred at room temperature for 1 hour. Then, a solution of 2.00 g of 2,3′,5′-trichloro-2,2-difluoroacetophenone in 5 ml of tetrahydrofuran was added dropwise in the reaction mixture under cooling with ice with stirring, after the completion of the addition dropwise, continued to stir at room temperature for 1 hour. After the completion of the reaction, the reaction mixture was poured in 50 ml of ice water, extracted with ethyl acetate (50 ml×1), the organic phase was dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with hexane to obtain 1.50 g of the aimed product as yellow oily substance.
  • 1H NMR (CDCl3, Me4Si, 300 MHz) 7.40 (s, 1H), 7.35 (s, 2H), 5.99 (s, 1H), 5.65 (s, 1H).
    • Step 3: Production of 4-[5-chlorodifluoromethyl-5-(3,5-dichlorophenyl)-4,5-dihydroisoxazol-3-yl]-2-methyl-N-(2,2,2-trifluoroethyl)benzoic acid amide
  • In a solution of 0.25 g of 4-chlorohydroxyiminomethyl-2-methyl-N-(2,2,2-trifluoroethyl)benzoic acid amide synthesized similarly to Steps 1 to 3 of Synthetic Example 7 and 0.26 g of 3,5-dichloro-1-[1-(chlorodifluorofluoromethyl)ethenyl]benzene in 3 ml of 1,2-dimethoxyethane, 0.43 g of potassium hydrogen carbonate and a small amount of water were added, and stirred at room temperature for 15 hours. After the completion of the reaction, the reaction mixture was filtered and thereby solid substance was excluded, and the filtrate was concentrated under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (2:3) to obtain 0.28 g of the aimed product as yellow oily substance.
  • 1H NMR (CDCl3, Me4Si, 300 MHz) 7.35-7.65 (m, 6H), 6.06 (t, J=6.1 Hz, 1H), 4.0-4.25 (m, 3H), 3.72 (d, J=17.1 Hz, 1H), 2.47 (s, 3H).
    • Synthetic Example 28 4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-N-methoxycarbonyl-N-(2-pyridylmethyl)benzoic acid amide (Compound of the present invention No. 6-043) Step 1: Production of 5-(3,5-dichlorophenyl)-3-(3-methyl-4-nitrophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole
  • In a solution of 1.31 g of 3,5-dichloro-1-(1-trifluoromethylethenyl)benzene synthesized in Step 1 of Synthetic Example 3 and 1.17 g of -chloro-3-methyl-4-nitrobenzaldoxime in 10 ml of tetrahydrofuran, 1.15 g of potassium hydrogen carbonate and 1.50 g of water were added, and stirred at room temperature for 18 hours. After the completion of the reaction, tetrahydrofuran was removed from the reaction mixture, 3 ml of water was added, and stirred under colloing with ice for further 30 minutes. Precipitated crystal was filtered off, washed with 5 ml of water and then 5 ml of diisopropyl ether to obtain 1.29 g of the aimed product as white crystal.
  • Melting point 135.0 to 136.0° C.
  • 1H NMR (CDCl3, Me4Si, 300 MHz) 8.03 (d, J=7.5 Hz, 1H), 7.6-7.75 (m, 2H), 7.51 (bs, 2H), 7.44 (t, J=1.8 Hz, 1H), 4.11 (d, J=17.4 Hz, 1H), 3.73 (d, J=17.4 Hz, 1H), 2.64 (s, 3H).
    • Step 2: Production of 3-(4-amino-3-methylphenyl)-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole
  • In a solution of 1.23 g of 5-(3,5-dichlorophenyl)-3-(3-methyl-4-nitrophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole in 10 ml of ethyl acetate, 5.0 ml of water, 5.0 ml of acetic acid and 0.66 g of reduced iron were added and stirred at 100° C. for 2 hours. After the completion of the reaction, the reaction mixture was filtered through Celite, 20 ml of water was added in the filtrate, extracted with ethyl acetate (20 ml×2). The organic phases together were washed with 10 ml of saturated sodium hydrogen carbonate aqueous solution, and then with 10 ml of water, thereafter dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 1.05 g of crude aimed product as red-brown oily substance. The resulting product was used as such without purification for the next step.
  • 1H NMR (CDCl3, Me4Si, 300 MHz) 7.52 (s, 2H), 7.35-7.5 (m, 2H), 7.31 (dd, J=8.0, 2.0 Hz, 1H), 6.65 (d, J=8.4 Hz, 1H), 4.05 (d, J=17.1 Hz, 1H), 3.93 (bs, 2H), 3.64 (d, J=17.1 Hz, 1H), 2.17 (s, 3H).
    • Step 3: Production of 3-(4-bromo-3-methylphenyl)-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole
  • in a solution of 0.50 g of 3-(4-amino-3-methylphenyl)-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole in 1.0 ml of 1,4-dioxane and 2.0 ml of water, 1.0 ml of 47% hydrobromic acid was added, and stirred under reflux with heat for 1 hour. Then, the reaction mixture was cooled with ice, and a solution of 0.10 g of sodium nitrite in 1.0 ml of water was slowly added dropwise with stirring at a temperature of 5° C. or less, after the completion of the addition dropwise, continued to stir at the same temperature for further 1 hour. The diazo mixture was slowly added dropwise in a mixture of 1.0 ml of 47% hydrobromic acid and 0.28 g of copper (I) bromide at 60° C. with stirring, after the completion of the addition dropwise, continued to stir at 60° C. for further 2 hours. After the completion of the reaction, 10 ml of water was added in the reaction mixture, extracted with ethyl acetate (20 ml×2), the organic phases together were washed with water, then dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (1:10) to obtain 0.43 g of the aimed product as pale yellow crystal.
  • Melting point 105.0 to 108.0° C.
  • 1H NMR (CDCl3, Me4Si, 300 MHz) 7.59 (d, J=8.4 Hz, 1H), 7.45-7.55 (m, 3H), 7.42 (t, J=1.8 Hz, 1H), 7.33 (dd, J=8.4, 2.1 Hz, 1H), 4.07 (d, J=17.1 Hz, 1H), 3.68 (d, J=17.1 Hz, 1H), 2.43 (s, 3H).
    • Step 4: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylbenzoic acid ethyl ester
  • In a solution of 15.0 g of 3-(4-bromo-3-methylphenyl)-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole in 60 ml of ethanol in an autoclave, 3.26 g of sodium acetate, 0.37 g of 1,1′-bis(diphenylphosphino) ferrocene and 0.08 g of palladium (II) acetate were added, and stirred under 2.0 MPa carbon monoxide atmosphere at 110° C. for 3 hours. After the completion of the reaction, the reaction mixture was left and cooled to room temperature, 200 ml of water was added and extracted with ethyl acetate (200 ml×2), the organic phase was washed with water, dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluted with ethyl acetate-hexane (1:8) to obtain 10.8 g of the aimed product as colorless clear liquid.
  • Refractive index nD 21.40° C.=1.5474
  • 1H NMR (CDCl3, Me4Si, 300 MHz) 7.95 (d, J=8.4 Hz, 1H), 7.45-7.65 (m, 4H), 7.43 (t, J=1.8 Hz, 1H), 4.37 (q, J=7.2 Hz, 2H), 4.10 (d, J=17.4 Hz, 1H), 3.71 (d, J=17.1 Hz, 1H), 2.62 (s, 3H), 1.40 (t, J=7.2 Hz, 3H).
    • Step 5: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl benzoic acid
  • In a solution of 10.79 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylbenzoic acid ethyl ester in 50 ml of ethanol and 10 ml of water, a solution of 2.0 g of sodium hydroxide in 10 ml of water was slowly added with stirring at room temperature. Then, the reaction mixture was stirred at 80° C. for 2 hours, after the completion of the reaction, ethanol was distilled off under reduced pressure. The residue was adjusted to pH 1-2 with concentrated hydrochloric acid with stirring at 50° C., then continued to stir at the same temperature for 1 hour and then at 5° C. for 1 hour. Presipitated crystal was filtered off, washed with water and dried to obtain 9.36 g of the aimed product as white crystal.
  • Melting point 146.0 to 148.5° C.
  • 1H NMR (CDCl3, Me4Si, 300 MHz) 8.12 (d, J=8.7 Hz, 1H), 7.5-7.7 (m, 2H), 7.52 (d, J=1.5 Hz, 2H), 7.43 (d, J=1.5 Hz, 1H), 4.11 (d, J=16.8 Hz, 1H), 3.73 (d, J=17.4 Hz, 1H), 2.69 (s, 3H).
    • Step 6: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-N-methoxycarbonyl-N-(2-pyridylmethyl)benzoic acid amide
  • In a solution of 1.00 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl benzoic acid in 30 ml of toluene, 0.43 g of thionyl chloride and 3 drops of N,N-dimethylformamide were added, and stirred at 90° C. for 1 hour. After the completion of the reaction, the solvent was distilled off under reduced pressure, and the residue was dissolved in 5 ml of tetrahydrofuran. In a solution of 0.40 g of N-(2-pyridylmethyl) carbamic acid methyl ester in 5 ml of tetrahydrofuran, 0.27 g of t-butoxy potassium was added at room temperature with stirring, and stirred at the same temperature for 3 minutes. Then, the above-mentioned solution of acid chloride in tetrahydrofuran was added dropwise in the reaction mixture, after the completion of the addition dropwise, continued to stir at the same temperature for further 1 hour. After the completion of the reaction, the reaction mixture was diluted with 60 ml of ethyl acetate, washed with 50 ml of water, then dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluted with ethyl acetate-hexane (1:2 to 1:1) to obtain 0.75 g of the aimed product as yellow resinous substance.
  • 1H NMR (CDCl3, Me4Si, 300 MHz) 8.56 (d, J=4.8 Hz, 1H), 7.65-7.7 (m, 1H), 7.5-7.55 (m, 4H), 7.35-7.45 (m, 2H), 7.15-7.3 (m, 2H), 5.21 (s, 2H), 4.09 (d, J=17.4 Hz, 1H), 3.70 (d, J=17.4 Hz, 1H), 3.58 (s, 3H), 2.40 (s, 3H).
    • Synthetic Example 29 4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylbenzoic acid amide (Compound of the Present Invention No. 5-066) Step 1: Production of 4-bromo-1-chloro-3-methylbenzaldoxime
  • In a solution of 82.0 g of 4-bromo-3-methylbenzaldoxime in 450 ml of tetrahydrofuran, 120.0 g of concentrated hydrochloric acid was added dropwise with stirring under ice cooling over 45 minutes. Then, 220 ml of 8% sodium hypochlorite aqueous solution was carefully added dropwise over 75 minutes so that the temperature of the reaction mixture would not exceed 5° C., after the completion of the addition, continued to stir at 10° C. or less further for 90 minutes. After the completion of the reaction, nitrogen gas was blown through the reaction mixture for 45 minutes and precipitated insoluble material was filtered off, and tetrahydrofuran was distilled off under reduced pressure. The remaining aqueous solution was extracted with 240.0 g of ethyl acetate. The organic phase was washed with water (240 ml×2) and then insoluble material was filtered off, the solvent was distilled off under reduced pressure to obtain 93.5 g of the aimed product as pale yellow crystal.
  • Melting point 77.0 to 78.0° C.
  • 1H NMR (CDCl3, Me4Si, 400 MHz) 8.00 (bs, 1H), 7.71 (d, J=2.2 Hz, 1H), 7.57 (d, J=8.4 Hz, 1H), 7.51 (dd, J=8.4, 2.2 Hz, 1H), 2.44 (s, 3H).
    • Step 2: Production of 3-(4-bromo-3-methylphenyl)-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole
  • In a solution of 22.7 g of 3,5-dichloro-1-(1-trifluoromethylethenyl)benzene produced in Step 1 of Synthetic Example 3 and 26.0 g of 4-bromo-chloro-3-methylbenzaldoxime in 120 ml of tetrahydrofuran, 15.7 g of potassium hydrogen carbonate was added, and stirred under reflux with heat for 5 hours. After the completion of the reaction, the reaction mixture was left and cooled to room temperature, insoluble material was filtered off, then the solvent was distilled off under reduced pressure. 150 ml of water was added in the residue, stirred at room temperature for 18 hours, and precipitated crystal was filtered off and dried to obtain 38.6 g of the aimed product as white crystal.
  • Melting point 105.0 to 108.0° C.
  • 1H NMR (CDCl3, Me4Si, 300 MHz) 7.59 (d, J=8.4 Hz, 1H), 7.45-7.55 (m, 3H), 7.42 (t, J=1.8 Hz, 1H), 7.33 (dd, J=8.4, 2.1 Hz, 1H), 4.07 (d, J=17.1 Hz, 1H), 3.68 (d, J=17.1 Hz, 1H), 2.43 (s, 3H).
    • Step 3: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylbenzoyl chloride
  • In a solution of 18.1 g of 3-(4-bromo-3-methylphenyl)-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisox azole and 3.94 g of sodium acetate in 42 ml of 1,2-dimethoxyethane and 42 ml of water in an autoclave, 0.42 g of triphenylphosphine and 0.09 g of palladium (II) acetate were added, and stirred under 1.5 MPa carbon monoxide atmosphere at 110° C. for 7 hours. After the completion of the reaction, the reaction mixture was left and cooled to room temperature, the solid was filtered off, then added in 100 ml of ethyl acetate. The organic phase was washed with 1% sodium hydrogen carbonate aqueous solution (70 ml×2), then with 1N hydrochloric acid (55 ml×2), dried with saturated sodium chloride aqueous solution and then the solvent was displaced by toluene. 2 drops of N,N-dimethylformamide was added in the resulting toluene solution, and 6.0 g of thionyl chloride was added dropwise with stirring at 80° C., and continued to stir at the same temperature further for 1.5 hour. After the completion of the reaction, insoluble material was filtered off, the solvent was distilled off under reduced pressure until the volume of the solvent was reduced to about one-third. Then, 50 ml of hexane was gradually added dropwise with stirring at 60° C., after the completion of the addition, left and cooled to room temperature with stirring, and continued to stir at room temperature further for 1 hour. Precipitated crystal was filtered off and dried to obtain 13.4 g of the aimed product as white crystal.
  • Melting point 140.5 to 143.0° C.
  • 1H NMR (CDCl3, Me4Si, 300 MHz) δ 8.25 (d, J=8.7 Hz, 1H), 7.64 (d, J=8.7 Hz, 1H), 7.59 (s, 1H), 7.51 (s, 2H), 7.43 (s, 1H), 4.11 (d, J=17.4 Hz, 1H), 3.73 (d, J=17.4 Hz, 1H), 2.60 (s, 3H).
    • Step 4: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylbenzoic acid amide
  • In a mixture of 3.0 g of concentrated ammonia water and 15 ml of tetrahydrofuran, a solution of 3.0 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylbenzoyl chloride in 20 ml of tetrahydrofuran was added dropwise, after the completion of the addition, continued to stir further for 18 hours. After the completion of the reaction, the solvent was distilled off under reduced pressure, the residue was dissolved in 50 ml of ethyl acetate, washed with 50 ml of water, dehydrated and dried with saturated sodium chloride aqueous solution and anhydrous sodium sulfate in that order, and the solvent was distilled off under reduced pressure to obtain 2.9 g of the aimed product as orange crystal.
  • Melting point 162.5 to 164.0° C.
  • 1H NMR (CDCl3, Me4Si, 400 MHz) δ 7.45-7.55 (m, 6H), 6.40 (bs, 1H), 6.00 (bs, 1H), 4.09 (d, J=17.0 Hz, 1H), 3.71 (d, J=17.0 Hz, 1H), 2.49 (s, 3H).
    • Synthetic Example 30 4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-N-(2,2,2-trifluoroethoxymethyl)benzoic acid amide (Compound of the Present Invention No. 5-480) Step 1: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-N-hydroxymethyl)benzoic acid amide
  • In a solution of 7.00 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylbenzoic acid amide synthesized in Synthetic Example 29 in 70 ml of 1,4-dioxane, 1.82 g of 37% formalin aqueous solution, 7.00 g of potassium carbonate and 15 ml of water were added, stirred at the same temperature for 3 hours. After the completion of the reaction, the reaction mixture was diluted by adding 200 ml of ethyl acetate, washed with water (50 ml×1) and then dehydrated and dried with saturated sodium chloride aqueous solution and anhydrous magnesium sulfate in that order, and filtered through silica gel, the solvent was distilled off under reduced pressure to obtain 7.00 g of crude aimed product as white crystal.
  • Melting point 69.0 to 73.0° C.
    • Step 2: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-N-(2,2,2-trifluoroethoxymethyl)benzoic acid amide
  • In a solution of 1.70 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-N-(hydroxymethyl)benzoic acid amide in 20 ml of dichloromethane, 0.68 g of thionyl chloride was added with stirring at room temperature, stirred at the same temperature for 2 hours, then the solvent was distilled off under reduced pressure, and the residue was dissolved in 10 ml of tetrahydrofuran. In 0.33 g of 60% oily sodium hydride suspended in 30 ml of tetrahydrofuran, 1.50 g of 2,2,2-trifluoroethanol was added dropwise with stirring under ice cooling, and stirred at the same temperature for 10 minutes. Then, the solution of benzoic acid chloride in tetrahydrofuran prepared above was added dropwise in the reaction mixture with stirring under ice cooling, after the completion of the addition, continued to stir at room temperature for 1 hour. After the completion of the reaction, 50 ml of water was added in the reaction mixture, extracted with ethyl acetate (70 ml×1), and the organic phase was dehydrated and dried with saturated sodium chloride aqueous solution and anhydrous magnesium sulfate in that order, and then the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (2:3) to obtain 1.20 g of the aimed product as colorless resinous substance.
  • 1H NMR (CDCl3, Me4Si, 400 MHz) δ 7.5-7.55 (m, 4H), 7.4-7.5 (m, 2H), 6.64 (t, J=6.4 Hz, 1H), 5.02 (d, J=7.2 Hz, 2H), 4.05-4.15 (m, 3H), 3.70 (d, J=17.4 Hz, 1H), 2.49 (s, 3H).
    • Synthetic Example 31 N-Carbamoylmethyl-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl benzoic acid amide (Compound of the Present Invention No. 5-137)
  • In a solution of 0.37 g of glycine amide hydrochloride and 0.71 g of pyridine in 20 ml of dichloromethane, a solution of 1.31 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylbenzoyl chloride synthesized in Step 3 of Synthetic Example 29 in 10 ml of dichloromethane was added dropwise with stirring under ice cooling, after the completion of the addition, stirred at room temperature for 3 hours, then 3.00 g of triethyl amine was added in the reaction mixture, and continued to stir at the same temperature further for 30 minutes. After the completion of the reaction, the solvent was distilled off under reduced pressure, 50 ml of ethyl acetate and 50 ml of water were added in the residue, and the organic phase was collected, and the aqueous phase was further extracted with ethyl acetate (50 ml×2). The organic phases together were dehydrated and dried with saturated sodium chloride aqueous solution and anhydrous sodium sulfate in that order, and the solvent was distilled off under reduced pressure, the residual solid was washed with hexane to obtain 1.24 g of the aimed product as white crystal.
  • Melting point 87.0 to 91.0° C.
  • 1H NMR (CDCl3, Me4Si, 300 MHz) δ 7.4-7.55 (m, 6H), 7.15-7.25 (m, 1H), 6.86 (s, 1H), 5.88 (s, 1H), 4.12 (d, J=5.1 Hz, 2H), 4.11 (d, J=17.4 Hz, 1H), 3.74 (d, J=17.4 Hz, 1H), 2.49 (s, 3H).
    • Synthetic Example 32 N-Aminomethyl-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl benzoic acid amide hydrochloride (Compound of the Present Invention No. 5-507)
  • In a solution of 0.47 g of [bis(trifluoroacetoxy) iodo]benzene in 12 ml of acetonitrile-water (1:1), a solution of 0.47 g of N-carbamoylmethyl-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl benzoic acid amide synthesized in Synthetic Example 31 was added with stirring at room temperature, and stirred at room temperature for 5 hours. After the completion of the reaction, 75 ml of water was added in the reaction mixture, 8 ml of concentrated hydrochloric acid was added, then washed with 100 ml of diethyl ether, and the organic phase was subjected to back extraction with 2N hydrochloric acid aqueous solution (20 ml×2). The aqueous phase was combined with the organic phase, water was distilled off, and the residual solid was washed with ethyl acetate to obtain 0.21 g of the aimed product as white crystal.
  • Melting point 155.0 to 157.0° C.
  • 1H NMR (CDCl3, Me4Si, 300 MHz) δ 9.0-9.1 (m, 1H), 7.4-7.7 (m, 8H), 4.64 (d, J=5.7 Hz, 2H), 4.16 (d, J=17.4 Hz, 1H), 3.80 (d, J=17.4 Hz, 1H), 2.50 (s, 3H).
    • Synthetic Example 33 N-[4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl benzoylaminomethyl]carbamic acid methyl ester (Compound of the Present Invention No. 5-515)
  • In a suspended solution of 0.13 g of N-aminomethyl-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl benzoic acid amide hydrochloride synthesized in Synthetic Example 32 in 4 ml of dichloromethane, 0.03 g of methyl chloroformate and 0.08 g of triethyl amine were added with stirring at room temperature, and stirred at room temperature for 3 hours. After the completion of the reaction, the solvent was distilled under reduced pressure, the residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (1:1) to obtain 0.06 g of the aimed product as colorless resinous substance.
  • 1H NMR (CDCl3, Me4Si, 300 MHz) δ 7.35-7.55 (m, 6H), 7.17 (bs, 1H), 6.12 (bs, 1H), 4.73 (t, J=6.6 Hz, 2H), 4.09 (d, J=17.4 Hz, 1H), 3.71 (d, J=17.4 Hz, 1H), 3.68 (s, 3H), 2.42 (s, 3H).
    • Synthetic Example 34 N-[4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-N-(2-tetrahydrofuranyl)benzoic acid amide (Compound of the Present Invention No. 5-494)
  • In a solution of 1.25 g of N-[4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl benzoic acid amide synthesized in Synthetic Example 29 and 0.32 g of 2,3-dihydrofuran in 30 ml of dichloromethane, 0.01 g of p-toluene sulfonic acid monohydrate was added with stirring at room temperature, and stirred at room temperature for 3 days. After the completion of the reaction, 30 ml of saturated sodium hydrogen carbonate aqueous solution was added in the reaction mixture, and extracted with ethyl acetate (30 ml×2), the organic phase was dehydrated and dried with saturated sodium chloride aqueous solution and anhydrous sodium sulfate in that order, and the solvent was distilled under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (1:1) to obtain 1.18 g of the aimed product as colorless resinous substance.
  • Melting point 144.0 to 147.0° C.
  • 1H NMR (CDCl3, Me4Si, 300 MHz) δ 7.3-7.55 (m, 6H), 6.49 (d, J=8.1 Hz, 1H), 5.8-5.9 (m, 1H), 4.09 (d, J=17.1 Hz, 1H), 3.8-4.0 (m, 2H), 3.72 (d, J=17.1 Hz, 1H), 2.42 (s, 3H), 2.2-2.4 (m, 1H), 1.8-2.1 (m, 3H).
    • Synthetic Example 35 4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-N-methyl-N-(2-tetrahydrothienyl)benzoic acid amide (Compound of the Present Invention No. 6-133)
  • In a solution of 0.43 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-N-methyl benzoic acid amide synthesized similarly to Synthetic Example 29 and 0.20 g of triethylamine in 5 ml of toluene, 0.45 g of trimethyl silyl trifurate was added and stirred vigorously. 10 minutes after the stirring, the reaction mixture was cooled to 0° C., 0.10 g of tetrahydrothiophen-1-oxide and 0.06 g of zinc iodide were added with stirring, and continued to stir at room temperature further for 4 days. After the completion of the reaction, 10 ml of ice water was added in the reaction mixture, and extracted with ethyl acetate (20 ml×2), the organic phase was dehydrated and dried with saturated sodium chloride aqueous solution and anhydrous sodium sulfate in that order, and the solvent was distilled under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (1:2) to obtain 0.09 g of the aimed product as white crystal.
  • Melting point 146.0 to 151.0° C.
  • 1H NMR (CDCl3, Me4Si, 300 MHz) δ 7.4-7.7 (m, 5H), 7.15-7.25 (m, 1H), 6.65-6.75 and 5.3-5.4 (m, 1H), 4.09 (d, J=17.1 Hz, 1H), 3.71 (d, J=17.1 Hz, 1H), 3.12 and 2.77 (s, 3H), 2.85-3.15 (m, 2H), 2.33 and 2.30 (s, 3H), 1.7-2.3 (m, 4H).
    • Synthetic Example 36 4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-ethenyl-2-methylbenzoic acid amide (Compound of the Present Invention No. 5-660)
  • In a solution of 0.50 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-2-methyl benzoic acid amide synthesized in Synthetic Example 29, 0.865 g of ethyl vinyl ether and 0.022 g of 1,10-phenanthroline in 10 ml of 1,2-dimethoxyethane, 0.04 g of bis(trifluoroacetoxy) palladium (II) was added and stirred at room temperature for 19 hours. After the completion of the reaction, 30 ml of water was added in the reaction mixture, and extracted with ethyl acetate (40 ml×1), the organic phase was dehydrated and dried with saturated sodium chloride aqueous solution and anhydrous sodium sulfate in that order, then filtered through silica gel, and the solvent was distilled under reduced pressure to obtain 0.45 g of the aimed product as pale yellow resinous substance.
  • 1H NMR (CDCl3, Me4Si, 300 MHz) δ 7.3-7.6 (m, 7H), 7.05-7.25 (m, 1H), 4.75 (d, J=15.6 Hz, 1H), 4.57 (d, J=8.8 Hz, 1H), 4.09 (d, J=17.4 Hz, 1H), 3.70 (d, J=17.1 Hz, 1H), 2.50 (s, 3H).
    • Synthetic Example 37 4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylbenzhydroxamic acid N-(2,2,2-trifluoroethyl) carbamic acid anhydride (Compound of the Present Invention No. 5-663)
  • In a solution of 0.30 g of hydroxylamine hydrochloride in 10 ml of methanol, a solution of 0.65 g of potassium hydroxide in 5 ml of methanol was added, then a solution of 1.00 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylbenzoic acid methyl ester synthesized similarly to Steps 1 to 4 of Synthetic Example 28 in 10 ml of methanol was added, and stirred at 40° C. for 1 hour. After the completion of the reaction, the solvent was distilled off under reduced pressure, 10 ml of acetic acid aqueous solution (1:1) was added in the residue, and extracted with ethyl acetate (20 ml×2), the organic phase was dehydrated and dried with saturated sodium chloride aqueous solution and anhydrous sodium sulfate in that order, and the solvent was distilled under reduced pressure. Toluene was added in the residue and the remaining acetic acid was distilled off azeotropically to to obtain 1.01 g of crude 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylbenzhydroxamic acid as white crystal.
  • In a solution of 0.16 g of carbonyl diimidazole in 2 ml of tetrahydrofuran, 0.10 g of 2,2,2-trifluoroethylamine was added, and stirred at room temperature for 1 hour. Then, a solution of 0.10 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylbenzhydroxamic acid in 2 ml of tetrahydrofuran was added in the reaction mixture, and continued to stir at room temperature further for 1 hour. After the completion of the reaction, the solvent was distilled off under reduced pressure, 10 ml of water was added in the residue, and extracted with ethyl acetate (10 ml×1). The organic phase was washed with 5 ml of 2N hydrochloric acid aqueous solution, dehydrated and dried with saturated sodium chloride aqueous solution and anhydrous sodium sulfate in that order, and the solvent was distilled under reduced pressure. The residue was purified with silica gel thin-layer chromatography (Kanto Chemical Co., Ltd.: PLC plates silica gel 60 F254 20×20 cm layer thickness 2 mm) that was developed with ethyl acetate-hexane (1:1) to obtain 0.12 g of the aimed product as white crystal.
  • Melting point 111.0 to 114.0° C.
  • 1H NMR (CDCl3, Me4Si, 300 MHz) δ 9.08 (bs, 1H), 7.4-7.6 (m, 6H), 6.07 (bs, 1H), 4.08 (d, J=17.4 Hz, 1H), 3.8-3.95 (m, 2H), 3.70 (d, J=17.4 Hz, 1H), 2.56 (s, 3H).
  • The compounds of the present invention can be produced according to the above-mentioned production methods and working examples. The examples of the compounds produced similarly to Synthetic Examples 1 to 37 are shown in Tables 7 to 20 to which the present invention is not limited. In the meantime, in Tables, the indication “Et” means ethyl, hereinafter similarly thereto, “n-Pr” and “Pr-n” mean normal propyl, “i-Pr” and “Pr-i” mean isopropyl, “c-Pr” and “Pr-c” mean cyclopropyl, “n-Bu” and “Bu-n” mean normal butyl, “s-Bu” and “Bu-s” mean secondary butyl, “i-Bu” and “Bu-i” mean isobutyl, “t-Bu” and “Bu-t” mean tertiary butyl, “c-Bu” and “Bu-c” mean cyclobutyl, “n-Pen” and “Pen-n” means normal pentyl, c-Pen” and “Pen-c” mean cyclopentyl, “n-Hex” and “Hex-n” mean normal hexyl, “c-Hex” and “Hex-c” mean cyclohexyl, “Ph” means phenyl, “TMS” means trimethylsilyl, “.Q1” means hydrochloride, “.Q2” means p-toluenesulfonate, “.Q3” means fumarate, “.Q4” means maleate, “.Q5” means triethylamine salt, and in Tables, aromatic heterocyclic rings of D-1a to D-54b are the following structures, respectively.
  • Figure US20150105398A1-20150416-C00064
    Figure US20150105398A1-20150416-C00065
    Figure US20150105398A1-20150416-C00066
    Figure US20150105398A1-20150416-C00067
    Figure US20150105398A1-20150416-C00068
    Figure US20150105398A1-20150416-C00069
    Figure US20150105398A1-20150416-C00070
  • in Tables, saturated heterocyclic rings of E-4-a to E-43a are the following structures, respectively,
  • Figure US20150105398A1-20150416-C00071
    Figure US20150105398A1-20150416-C00072
  • In Tables, partially saturated heterocyclic ring of M-5a is the following structure
  • Figure US20150105398A1-20150416-C00073
  • In Tables, T-4 to T-51 are the following structures, respectively
  • Figure US20150105398A1-20150416-C00074
    Figure US20150105398A1-20150416-C00075
    Figure US20150105398A1-20150416-C00076
  • In addition, in Tables, the number showing the substitution position of substituents (X)m and (Y)n correspond to the position number indicated in the following structural formulae. The indication “-” means no-substitution.
    Further, in Tables, the indication of “Mw” shows the calculated value of molecular weight, the indication of “M++H” shows the measured value of molecular ion peak, and “*1”, “*2” or “*3” means “resinous”, “oily” or “decomposition”, respectively.
  • TABLE 7
    Figure US20150105398A1-20150416-C00077
    No (X)m R3 R1 Mw M+ + H
    1-001 — C(O)OCH3 CH2CF3 406.36 407.00
    1-002 — C(O)OCH3 CH2Ph 414.46 415.07
    1-003 2-F C(O)OCH3 CH2CF3 424.35 424.99
    1-004 2-Cl C(O)OCH3 CH2CF3 440.81 440.94
    1-005 3-Br CF3 CH2Ph 503.31 502.75
    1-006 4-Br CF3 CH2CF3 495.21 494.68
    1-007 4-Br CF3 CH2Ph 503.31 502.74
    1-008 3-CH3 CF3 CH2CF3 430.34 430.91
    1-009 3-CH3 CF3 CH2Ph 438.44 438.95
    1-010 4-CH3 CF3 CH2CF3 430.34 430.92
    1-011 4-CH3 CF3 CH2Ph 438.44 438.91
    1-012 4-Bu-t CF3 CH2CF3 472.42 472.94
    1-013 4-Bu-t CF3 CH2Ph 480.52 480.99
    1-014 2-CF3 C(O)OCH3 CH2CF3 474.36 474.87
    1-015 3-CF3 CF3 CH2CF3 484.32 484.78
    1-016 3-CF3 CF3 CH2Ph 492.41 492.82
    1-017 4-CF3 CF3 CH2CF3 484.32 484.80
    1-018 4-CF3 CF3 CH2Ph 492.41 492.85
    1-019 2-OCH3 C(O)OCH3 CH2CF3 436.39 436.99
    1-020 3-OCH3 CF3 CH2CF3 446.34 446.89
    1-021 3-OCH3 CF3 CH2Ph 454.44 454.94
    1-022 4-OCH3 CF3 CH2CF3 446.34 446.89
    1-023 4-OCH3 CF3 CHPh 454.44 454.91
    1-024 4-OCH3 C(O)OCH3 CH2CF3 436.39 437.00
    1-025 3-OCF3 CF3 CH2CF3 500.31 500.76
    1-026 3-OCF3 CF3 CH2Ph 508.41 508.80
    1-027 4-OCF3 CF3 CH2CF3 500.31 500.76
    1-028 4-OCF3 CF3 CH2Ph 508.41 508.82
    1-029 4-OPh CF3 CH2CF3 508.41 508.85
    1-030 4-OPh CF3 CH2Ph 516.51 516.88
    1-031 4-SCH 3 CF3 CH2CF3 462.41 462.84
    1-032 4-SCH3 CF3 CH2Ph 470.51 470.88
    1-033 4-SO2CH3 CF3 CH2CF3 494.41 494.86
    1-034 3-NHC(O)CH3 CF3 CH2CF3 473.37 473.90
    1-035 3-NHC(O)CH3 CF3 CH2Ph 481.47 481.93
    1-036 4-NHC(O)CH3 CF3 CH2CF3 473.37 473.81
    1-037 4-NHC(O)CH3 CF3 CH2Ph 481.47 481.94
    1-038 4-N(CH3)2 CF3 CH2CF3 459.38 459.90
    1-039 4-N(CH3)2 CF3 CH2Ph 467.48 467.94
    1-040 3-NO2 CF3 CH2CF3 461.31 461.82
    1-041 3-NO2 CF3 CH2Ph 469.41 469.86
    1-042 3-TMS CF3 CH2CF3 488.50 488.87
    1-043 3-CN CF3 CH2Ph 449.42 449.89
    1-044 4-CN CF3 CH2Ph 449.42 449.89
    1-045 3-CHO CF3 CH2CF3 444.33 444.89
    1-046 3-C(O)CH3 CF3 CH2CF3 458.35 458.82
    1-047 3-C(O)CH3 CF3 CH2Ph 466.45 466.81
    1-048 4-C(O)CH3 CF3 CH2CF3 458.35 458.80
    1-049 4-C(O)CH3 CF3 CH2Ph 466.45 466.86
    1-050 3-C(O)OEt CF3 CH2CF3 488.38 488.89
    1-051 3-C(O)OEt CF3 CH2Ph 496.48 496.92
    1-052 4-Ph CF3 CH2CF3 492.41 492.81
    1-053 3,4-F2 CF3 CH2Pr-c 424.36 424.91
    1-054 3,4-F2 CF3 CH2Ph 460.40 460.87
    1-055 3,5-F2 CF3 CH2CF3 452.30 452.84
    1-056 3,5-F2 CF3 CH2Ph 460.40 460.89
    1-057 3-Cl-4-F CF3 CH2CF3 468.75 468.76
    1-058 3-Cl-4-F CF3 CH2Ph 476.85 476.80
    1-059 2,5-Cl2 CF3 CH2CF3 485.21 484.79
    1-060 2,5-Cl2 CF3 CH2Ph 493.30 492.82
    1-061 2,5-Cl2 CF3 CH2(D-47a) 494.29 493.84
    1-062 3,4-Cl2 CF3 Et 431.24 430.93
    1-063 3,4-Cl2 CF3 n-Pr 445.27 444.94
    1-064 3,4-Cl2 CF3 i-Pr 445.27 444.94
    1-065 3,4-Cl2 CF3 n-Bu 459.29 458.97
    1-066 3,4-Cl2 CF3 CH2Pr-c 457.28 456.94
    1-067 3,4-Cl2 CF3 s-Bu 459.29 458.93
    1-068 3,4-Cl2 CF3 t-Bu 459.29 458.92
    1-069 3,4-Cl2 CF3 c-Bu 457.27 456.79
    1-070 3,4-Cl2 CF3 n-Pen 473.32 473.02
    1-071 3,4-Cl2 CF3 CH2Bu-s 473.32 472.82
    1-072 3,4-Cl2 CF3 CH2Bu-t 473.32 472.94
    1-073 3,4-Cl2 CF3 CH(CH3)Pr-n 473.32 472.94
    1-074 3,4-Cl2 CF3 c-Pen 471.31 470.99
    1-075 3,4-Cl2 CF3 n-Hex 487.35 486.96
    1-076 3,4-Cl2 CF3 c-Hex 485.33 484.93
    1-077 3,4-Cl2 CF3 CH2Hex-c 499.35 498.88
    1-078 3,4-Cl2 CF3 CH2(T-39) 539.42 538.88
    1-079 3,4-Cl2 CF3 CH2CH2Cl 465.69 464.73
    1-080 3,4-Cl2 CF3 CH2CF3 485.21 484.85
    1-081 3,4-Cl2 CF3 CH2CF2CF2CF3 585.23 584.65
    1-082 3,4-Cl2 CF3 CH2CH(CH3)OH(R) 461.26 460.78
    1-083 3,4-Cl2 CF3 CH2CH(CH3)OH(S) 461.26 460.82
    1-084 3,4-Cl2 CF3 CH2CH(CH3)OC(O)NHEt(S) 532.34 531.78
    1-085 3,4-Cl2 CF3 CH(CH3)CH2OCH3 475.29 474.94
    1-086 3,4-Cl2 CF3 CH2CH(Et)OH 475.29 474.82
    1-087 3,4-Cl2 CF3 CH(Et)CH2OCH3 489.32 488.95
    1-088 3,4-Cl2 CF3 CH2CH(OCH3)2 491.29 490.80
    1-089 3,4-Cl2 CF3 CH2CH2CH2OH 461.27 460.97
    1-090 3,4-Cl2 CF3 CH2CH2CH2OCH3 475.29 474.98
    1-091 3,4-Cl2 CF3 CH2(T-13) 515.35 514.80
    1-092 3,4-Cl2 CF3 CH2(E-11c) 517.33 516.79
    1-093 3,4-Cl2 CF3 CH2CH2SCH3 477.33 476.75
    1-094 3,4-Cl2 CF3 CH2CH2SBu-t 519.41 518.96
    1-095 3,4-Cl2 CF3 CH2CH2CH2SCH3 491.35 490.92
    1-096 3,4-Cl2 CF3 CH2CH2NHC(O)OBu-t 546.37 545.75
    1-097 3,4-Cl2 CF3 CH2CH2CH2Si(OCH3)3 565.44 564.77
    1-098 3,4-Cl2 CF3 CH2CH2CH2Si(CH3)(OEt)2 577.49 576.79
    1-099 3,4-Cl2 CF3 CH2C(O)OCH3 475.25 474.89
    1-100 3,4-Cl2 CF3 CH2CH2C(O)OCH3 489.28 488.80
    1-101 3,4-Cl2 CF3 CH2C(O)NH2 460.24 459.74
    1-102 3,4-Cl2 CF3 CH2CH═CH2 443.25 442.81
    1-103 3,4-Cl2 CF3 CH2CH2(T-17) 511.36 510.76
    1-104 3,4-Cl2 CF3 CH2C≡CH 441.24 440.91
    1-105 3,4-Cl2 CF3 CH2Ph 493.31 492.86
    1-106 3,4-Cl2 CF3 CH2(Ph-2-F) 511.30 510.80
    1-107 3,4-Cl2 CF3 CH2(Ph-3-F) 511.30 510.81
    1-108 3,4-Cl2 CF3 CH2(Ph-2-Cl) 527.75 526.74
    1-109 3,4-Cl2 CF3 CH2(Ph-3-Cl) 527.75 526.75
    1-110 3,4-Cl2 CF3 CH2(Ph-2-CH3) 507.33 506.78
    1-111 3,4-Cl2 CF3 CH2(Ph-4-CH3) 507.33 506.73
    1-112 3,4-Cl2 CF3 CH2(Ph-4-Bu-t) 549.41 548.77
    1-113 3,4-Cl2 CF3 CH2(Ph-2-CF3) 561.30 560.72
    1-114 3,4-Cl2 CF3 CH2(Ph-3-CF3) 561.30 560.69
    1-115 3,4-Cl2 CF3 CH2(Ph-4-CF3) 561.30 560.97
    1-116 3,4-Cl2 CF3 CH2(Ph-2-OCH3) 523.33 522.77
    1-117 3,4-Cl2 CF3 CH2(Ph-3-OCH3) 523.33 522.74
    1-118 3,4-Cl2 CF3 CH2(Ph-4-OCH3) 523.33 522.68
    1-119 3,4-Cl2 CF3 CH2(Ph-3-OCF3) 577.30 576.69
    1-120 3,4-Cl2 CF3 CH2(Ph-4-SO2CH3) 571.40 570.71
    1-121 3,4-Cl2 CF3 CH2[Ph-4-N(CH3)2] 536.37 535.81
    1-122 3,4-Cl2 CF3 CH2(Ph-3-NO2) 538.30 537.64
    1-123 3,4-Cl2 CF3 CH2(Ph-4-NO2) 538.30 537.66
    1-124 3,4-Cl2 CF3 CH2[Ph-4-C(O)OCH3] 551.34 550.74
    1-125 3,4-Cl2 CF3 CH2(Ph-2,5-F2) 529.29 528.72
    1-126 3,4-Cl2 CF3 CH2(Ph-2,6-F2) 529.29 528.81
    1-127 3,4-Cl2 CF3 CH2(Ph-3,5-F2) 529.29 528.73
    1-128 3,4-Cl2 CF3 CH2(Ph-3-Cl-4-F) 545.74 544.67
    1-129 3,4-Cl2 CF3 CH2(Ph-2,3-Cl2) 562.20 560.72
    1-130 3,4-Cl2 CF3 CH2(Ph-2,4-Cl2) 562.20 560.72
    1-131 3,4-Cl2 CF3 CH2(Ph-2,5-Cl2) 562.20 560.72
    1-132 3,4-Cl2 CF3 CH2(Ph-2,6-Cl2) 562.20 560.73
    1-133 3,4-Cl2 CF3 CH2(Ph-3,5-Cl2) 562.20 560.64
    1-134 3,4-Cl2 CF3 CH2(Ph-3-CF3-4-F) 579.29 578.70
    1-135 3,4-Cl2 CF3 CH2[Ph-3,4-(OCH3)2] 553.36 552.76
    1-136 3,4-Cl2 CF3 CH2(Ph-3-OCH2O-4) 537.31 536.73
    1-137 3,4-Cl2 CF3 CH2(1-Naph) 543.36 542.80
    1-138 3,4-Cl2 CF3 CH(CH3)Ph 507.34 506.88
    1-139 3,4-Cl2 CF3 CH(CH3)(Ph-3-Cl) 541.78 540.70
    1-140 3,4-Cl2 CF3 C(CH3)2Ph 521.37 520.99
    1-141 3,4-Cl2 CF3 CH2CH2Ph 507.34 507.01
    1-142 3,4-Cl2 CF3 CH2CH2(Ph-4-OPh) 599.44 598.95
    1-143 3,4-Cl2 CF3 CH2CH(CH3)Ph 521.37 520.93
    1-144 3,4-Cl2 CF3 CH2CHPh2 583.43 582.79
    1-145 3,4-Cl2 CF3 CH(CH3)CH2(Ph-4-Cl) 555.81 554.78
    1-146 3,4-Cl2 CF3 T-9 519.35 518.88
    1-147 3,4-Cl2 CF3 CH2CH2CH2Ph 521.37 520.97
    1-148 3,4-Cl2 CF3 CH2CH2SCH2Ph 553.43 552.75
    1-149 3,4-Cl2 CF3 CH2C(O)(Ph-4-OCH3) 551.34 550.66
    1-150 3,4-Cl2 CF3 CH2(D-1c)CH3 497.29 496.80
    1-151 3,4-Cl2 CF3 CH2(D-3a) 499.33 498.70
    1-152 3,4-Cl2 CF3 CH2(D-3b)CH3 513.36 512.74
    1-153 3,4-Cl2 CF3 CH2(D-47a) 494.29 493.84
    1-154 3,4-Cl2 CF3 CH2(D-47f ) 596.74 595.79
    1-155 3,4-Cl2 CF3 CH2(D-48a) 494.29 493.84
    1-156 3,4-Cl2 CF3 CH2(D-49a) 494.29 493.86
    1-157 3,4-Cl2 CF3 CH2(D-53b)CH3 509.31 508.78
    1-158 3,4-Cl2 CF3 CH2CH2(D-3a) 513.36 512.71
    1-159 3,4-Cl2 CF3 CH2CH2(D-47a) 508.32 507.76
    1-160 3,4-Cl2 CF3 CH2CH2(D-48a) 508.32 507.77
    1-161 3,4-Cl2 CF3 CH2CH2CH2(D-24a) 511.32 510.84
    1-162 3,4-Cl2 CF3 T-21 472.24 471.77
    1-163 3,4-Cl2 CF3 T-22 488.31 487.72
    1-164 3,4-Cl2 CF3 (D-8b)CH3 484.25 483.75
    1-165 3,4-Cl2 CF3 D-11c 581.35 580.66
    1-166 3,4-Cl2 CF3 D-21a 486.29 485.70
    1-167 3,4-Cl2 CF3 (D-21b)CH3 500.32 499.70
    1-168 3,4-Cl2 CF3 (D-21c)CH3 500.32 499.70
    1-169 3,4-Cl2 CF3 (D-21c)NO2 531.29 530.60
    1-170 3,4-Cl2 CF3 D-25d 533.33 532.73
    1-171 3,4-Cl2 CF3 D-48a 480.27 479.76
    1-172 3,4-Cl2 CF3 D-49a 480.27 479.76
    1-173 3,4-Cl2 CF3 OPr-n 461.27 460.94
    1-174 3,4-Cl2 CF3 N(CH3)2 446.26 445.92
    1-175 3,5-Cl2 CF3 CH2Pr-c 457.27 456.83
    1-176 3,5-Cl2 CF3 CH2CH2CF3 499.23 498.79
    1-177 3,5-Cl2 CF3 CH2CH2OEt 475.29 474.86
    1-178 3,5-Cl2 CF3 CH2CH2OCH2CH2OH 491.29 490.78
    1-179 3,5-Cl2 CF3 CH2CH(CH3)OH 461.27 460.88
    1-180 3,5-Cl2 CF3 CH2CH2CH2OEt 489.31 488.90
    1-181 3,5-Cl2 CF3 CH2CH2CH2OPr-i 503.34 502.86
    1-182 3,5-Cl2 CF3 CH2CH2SEt 491.35 490.99
    1-183 3,5-Cl2 CF3 CH2(Ph-3-Br) 572.20 570.68
    1-184 3,5-Cl2 CF3 CH2(Ph-3-OCH3) 523.33 522.80
    1-185 3,5-Cl2 CF3 CH2(Ph-4-OCH3) 523.33 522.74
    1-186 3,5-Cl2 CF3 CH2(Ph-4-OCF3) 577.30 576.75
    1-187 3,5-Cl2 CF3 CH2(Ph-4-SO2NH2) 572.38 571.78
    1-188 3,5-Cl2 CF3 CH2(Ph-3-NO2) 538.30 537.76
    1-189 3,5-Cl2 CF3 CH2(Ph-4-NO2) 538.30 537.76
    1-190 3,5-Cl2 CF3 CH2CH2(Ph-3-Cl) 541.78 540.71
    1-191 3,5-Cl2 CF3 CH2CH2(Ph-4-OCH3) 537.36 536.79
    1-192 3,5-Cl2 CF3 CH2CH2(Ph-3,4-Cl2) 576.22 574.60
    1-193 3,5-Cl2 CF3 CH2CH2[Ph-3,4-(OCH3)2] 567.38 566.77
    1-194 3,5-Cl2 CF3 CH2CH2OPh 523.33 522.85
    1-195 3,5-Cl2 CF3 Ph-4-OCH3 509.30 508.75
    1-196 3,5-Cl2 CF3 (D-21b)CH2C(O)OEt 572.38 571.70
    1-197 3,5-Cl2 CF3 (D-21c)Br 565.19 563.59
    1-198 3,5-Cl2 CF3 (D-21c)SO2(Ph-4-NO2) 671.45 670.55
    1-199 3,5-Cl2 CF3 D-21d 514.35 513.72
    1-200 3,5-Cl2 CF3 D-21e 536.35 535.70
    1-201 3,5-Cl2 CF3 D-21f 570.80 569.68
    1-202 3,5-Cl2 CF3 D-21g 570.80 569.68
    1-203 3,5-Cl2 CF3 D-21h 566.38 565.71
    1-204 3,5-Cl2 CF3 D-21i 566.38 565.76
    1-205 3,5-Cl2 CF3 D-21j 581.35 580.69
    1-206 3,5-Cl2 CF3 NHPh 494.29 493.81
    1-207 3,5-Br2 CF3 CH2CF3 574.11 572.49
    1-208 3,5-Br2 CF3 CH2Ph 582.21 580.61
    1-209 3-CH3-4-F CF3 CH2Ph 456.43 456.87
    1-210 3,4-(CH3)2 CF3 CH2CF3 444.37 444.89
    1-211 3,4-(CH3)2 CF3 CH2Ph 452.47 452.94
    1-212 3,5-(CH3)2 CF3 CH2CF3 444.37 444.86
    1-213 3,5-(CH3)2 CF3 CH2Ph 452.47 452.95
    1-214 3,5-(CF3)2 CF3 CH2CF3 552.31 552.72
    1-215 3,5-(CF3)2 CF3 CH2Ph 560.41 560.76
    1-216 3-OEt-4-Cl CF3 CH2CF3 494.81 494.76
    1-217 3-OEt-4-Cl CF3 CH2Ph 502.91 502.81
    1-218 3,4-(OCH3)2 CF3 CH2CF3 476.37 476.83
    1-219 3,4-(OCH3)2 CF3 CH2Ph 484.47 484.90
    1-220 3-OCH2O-4 CF3 CH2Pr-c 432.39 432.89
    1-221 3-OCH2O-4 CF3 CH2Ph 468.42 468.86
    1-222 3,5-(CHO)2 CF3 CH2CF3 472.34 472.92
    1-223 3-CH═CHCH═CH-4 CF3 CH2CF3 466.38 466.83
    1-224 3-CH═CHCH═CH-4 CF3 CH2Ph 474.47 74.86
    1-225 3,4,5-F3 CF3 CH2CF3 470.29 470.77
    1-226 3,4,5-F3 CF3 CH2Ph 478.39 478.82
  • TABLE 8
    Figure US20150105398A1-20150416-C00078
    No. (X)m (Y)n R2 R1 Mw M+ + H
    2-001 3,4-F2 — CH3 CH2Ph 474.42 474.88
    2-002 3,4-Cl2 — CH3 CH3 431.24 430.91
    2-003 3,4-Cl2 — Et Et 459.29 458.94
    2-004 3,4-Cl2 — CH3 n-Bu 473.32 472.97
    2-005 3,4-Cl2 — CH3 i-Bu 473.32 472.89
    2-006 3,4-Cl2 — —CH2CH2CH2CH2— 457.28 456.85
    2-007 3,4-Cl2 — —CH2CH2CH2CH2CH2— 471.31 470.84
    2-008 3,4-Cl2 — —CH2CH2CH2CH2CH(CH3)— 485.33 484.83
    2-009 3,4-Cl2 — —CH2CH2CH2CH(CH3)CH2— 485.33 484.82
    2-010 3,4-Cl2 — —CH2CH(CH3)CH2CH(CH3)CH2— 499.35 498.82
    2-011 3,4-Cl2 — —CH2CH2OCH2CH2— 473.28 472.75
    2-012 3,4-Cl2 — —CH2CH(CH3)OCH(CH3)CH2— 501.33 500.77
    2-013 3,4-Cl2 — —CH2CH2SCH2CH2— 489.34 488.74
    2-014 3,4-Cl2 — —CH2CH2N(CHO)CH2CH2— 500.30 499.76
    2-015 3,4-Cl2 — CH3 CH2CH═CH2 457.27 456.87
    2-016 3,4-Cl2 — CH2CH═CH2 CH2CH═CH2 483.31 482.85
    2-017 3,4-Cl2 — CH3 CH2C≡CH 455.26 454.86
    2-018 3,4-Cl2 — CH3 CH2Ph 507.34 506.93
    2-019 3,4-Cl2 — Et CH2(D-48e)Cl 556.79 555.73
    2-020 3,5-Cl2 — Et Et 459.29 458.85
    2-021 3,5-Cl2 — CH3 CH2Ph 507.33 506.79
    2-022 3,5-Cl2 — Et CH2Ph 521.36 520.79
    2-023 3,5-Cl2 — CH2Ph CH2Ph 583.43 582.79
    2-024 3,5-Cl2 2-CH3 H CH2CH2OH 461.26 460.99
    2-025 3,5-Cl2 2-CH3 H CH2CH2OPr-n 503.34 502.99
    2-026 3,5-Cl2 2-CH3 H CH2CH2OPr-i 503.34 502.98
    2-027 3,5-Cl2 2-CH3 H CH2CH2OCH2CH2OH 505.31 504.95
    2-028 3,5-Cl2 2-CH3 H CH2CH2OPh 537.36 536.94
    2-029 3,5-Cl2 2-CH3 H CH(CH3)CH2OCH3 489.31 488.98
    2-030 3,5-Cl2 2-CH3 H CH2CH2N(CH3)2 488.33 487.98
    2-031 3,5-Cl2 2-CH3 H CH(Ph)C(O)OCH3(R) 565.37 564.84
    2-032 3,5-Cl2 2-CH3 H CH(Ph)C(O)OCH3(S) 565.37 564.92
    2-033 3,5-Cl2 2-CH3 H CH2CH2C(O)OCH3 503.30 502.91
    2-034 3,5-Cl2 2-CH3 H CH2(Ph-4-OCH3) 537.36 536.98
    2-035 3,5-Cl2 2-CH3 H CH2(Ph-4-CN) 532.34 531.94
    2-036 3,5-Cl2 2-CH3 H CH2CH2(D-47a) 522.35 521.94
    2-037 3,5-Cl2 2-CH3 H T-29b 562.32 559.80*
    2-038 3,5-Cl2 2-CH3 H NHCH2C(O)OEt 518.31 517.93
    2-039 3,5-Cl2 2-CH3 H NHCHO 460.23 457.86*
    2-040 3,5-Cl2 2-CH3 H NHC(O)CH2(D-3a) 556.38 553.71*
    2-041 3,5-Cl2 2-CH3 H N(CH3)C(S)NH2 505.34 504.82
    2-042 3,5-Cl2 2-CH3 H N(CH3)C(S)NHCH3 519.37 518.88
    2-043 3,5-Cl2 2-CH3 H T-40 530.37 529.98
    2-044 3,5-Cl2 2-CH3 H NH(Ph-2-F) 526.31 525.92
    2-045 3,5-Cl2 2-CH3 H NH(Ph-3-F) 526.31 525.92
    2-046 3,5-Cl2 2-CH3 H NH(Ph-4-F) 526.31 523.89*
    2-047 3,5-Cl2 2-CH3 H NH(Ph-4-Br) 587.22 585.91
    2-048 3,5-Cl2 2-CH3 H NH(Ph-4-CH3) 522.35 521.93
    2-049 3,5-Cl2 2-CH3 H NH(Ph-4-Pr-i) 550.40 549.94
    2-050 3,5-Cl2 2-CH3 H NH(Ph-4-OCF3) 592.32 591.97
    2-051 3,5-Cl2 2-CH3 H NH(Ph-4-CN) 533.33 533.01
    2-052 3,5-Cl2 2-CH3 H N(CH3)(D-47d)CF3 591.33 590.99
    2-053 3,5-Cl2 2-CH3 H N═CHC(CH3)═CHPh 560.39 559.95
    2-054 3,5-Cl2 2-CH3 H D-47a 494.29 493.94
    2-055 3,5-Cl2 2-CH3 H D-49a 494.29 493.97
    2-056 3-OCH2O-4 — CH3 CH2Ph 482.45 482.86
    2-057 3,5-Cl2 2-CH3 C(O)OCH3 CH2CH═CH2 515.31 514.97
    2-058 3,5-Cl2 2-CH3 C(O)OPr-i CH2CH═CH2 543.36 541.04*
    2-059 3,5-Cl2 2-CH3 H C(O)OCH2CH2Cl 523.72 522.84
    2-060 3,5-Cl2 2-CH3 H C(O)OCH2CHCl2 558.16 554.92*
    2-061 3,5-Cl2 2-CH3 H C(O)OCH2CCl3 592.61 588.88*
    2-062 3,5-Cl2 2-CH3 H C(O)OCH2CH2CF3 557.27 557.03
    2-063 3,5-Cl2 2-CH3 H C(O)OCH(CH2Cl)2 572.19 570.94*
    2-064 3,5-Cl2 2-CH3 H C(O)OCH(CF3)2 611.24 608.86*
    2-065 3,5-Cl2 2-CH3 H C(O)OCH(CH3)CHClCH3 551.77 548.95*
    2-066 3,5-Cl2 2-CH3 H C(O)OCH2CH2CH2CH2Cl 551.77 550.99
    2-067 3,5-Cl2 2-CH3 H C(O)OCH2C(CF3)2CH3 639.29 636.95*
    2-068 3,5-Cl2 2-CH3 H T-25 501.33 502.05
    2-069 3,5-Cl2 2-CH3 H (D-21c)C(O)OEt 571.38 572.04

    In Table above, the indication of “*” shows the measured value of molecular ion peak of M+H measured with negative mode.
  • TABLE 9
    Figure US20150105398A1-20150416-C00079
    No. (X)m R3 R1 m.p. (° C.)
    3-001 — CF3 CH2CF3 172.0-173.0
    3-002 3-Cl CF3 CH2CF3 157.0-158.0
    3-003 3-Cl CF3 CH2Ph 168.0-169.0
    3-004 4-Cl CF3 CH2CF3 190.0-191.0
    3-005 4-Cl CF3 CH2Ph 212.0-214.0
    3-006 3-Br CF3 CH2CF3 132.0-135.0
    3-007 3-OCF3 CF3 CH2(D-47a) 145.0-147.0
    3-008 3-OCH2Ph CF3 CH2CF3 146.0-149.0
    3-009 3-OCH2(Ph-2-Cl) CF3 CH2CF3 158.0-159.0
    3-010 3-OCH2(Ph-2-Cl) CF3 CH2(D-47a) *1
    3-011 3-SEt CF3 CH2CF3 105.0-106.0
    3-012 3-CN CF3 CH2CF3  93.0-96.0
    3-013 4-CN CF3 CH2CF3 149.0-151.0
    3-014 3-CH═NOH CF3 CH2CF3 168.0-169.0
    3-015 3-CH═NOCH3 CF3 CH2CF3 *1
    3-016 4-C(CH3)═NOCH3(E) CF3 CH2CF3 160.0-162.0
    3-017 4-C(CH3)═NOCH3(Z) CF3 CH2CF3 *1
    3-018 3,4-F2 CF3 CH2CF3 150.0-152.0
    3-019 2,4-Cl2 CF3 CH2CF3 149.0-151.0
    3-020 3,4-Cl2 H CH2CF3 161.0-162.0
    3-021 3,4-Cl2 H CH2Ph 147.0-148.0
    3-022 3,4-Cl2 CH3 CH2Pr-c 157.0-158.0
    3-023 3,4-Cl2 CH3 CH2CF3 120.0-122.0
    3-024 3,4-Cl2 CH3 CH2Ph 153.0-155.0
    3-025 3,4-Cl2 CF3 CH3 139.0-140.0
    3-026 3,4-Cl2 CF3 c-Pr 193.0-194.0
    3-027 3,4-Cl2 CF3 i-Bu 158.0-159.0
    3-028 3,4-Cl2 CF3 CH2Bu-c 177.0-179.0
    3-029 3,4-Cl2 CF3 CH2CH(Et)Bu-n 125.0-127.0
    3-030 3,4-Cl2 CF3 CH2CF2CF3 171.0-173.0
    3-031 3,4-Cl2 CF3 CH2(E-4a) 136.0-138.0
    3-032 3,4-Cl2 CF3 CH(CH3)CH2SCH3 145.0-147.
    3-033 3,4-Cl2 CF3 C(CH3)2CH2SCH3 150.0-152.0
    3-034 3,4-Cl2 CF3 C(CH3)2CH2S(O)CH3 *1
    3-035 3,4-Cl2 CF3 C(CH3)2CH2SO2CH3 161.0-163.0
    3-036 3,4-Cl2 CF3 CH2CH2CH2C(O)OEt 105.0-107.0
    3-037 3,4-Cl2 CF3 CH2(Ph-4-F) 155.0-156.0
    3-038 3,4-Cl2 CF3 CH2(Ph-4-Cl) 191.0-193.0
    3-039 3,4-Cl2 CF3 CH2(Ph-3-CH3) 198.0-200.0
    3-040 3,4-Cl2 CF3 CH2(Ph-3,4-Cl2) 161.0-162.0
    3-041 3,4-Cl2 CF3 CH2CH(Ph)OH 211.0-213.0
    3-042 3,4-Cl2 CF3 CH2C(O)(Ph-4-Br) 193.0-195.0
    3-043 3,4-Cl2 CF3 CH2(D-1a) 179.0-180.0
    3-044 3,4-Cl2 CF3 CH2(D-48e)Cl 154.0-157.0
    3-045 3,4-Cl2 CF3 CH2(D-50d) 183.0-186.0
    3-046 3,4-Cl2 CF3 CH2CH2(D-49a) 113.0-116.0
    3-047 3,4-Cl2 CF3 NHPh 160.0-162.0
    3-048 3,4-Cl2 CF3 Ph 208.0-210.0
    3-049 3,4-Cl2 CF3 Ph-2-CH3-4-Cl 237.0-238.0
    3-050 3,4-Cl2 CF3 D-35a 238.0-241.0
    3-051 3,4-Cl2 CF3 D-47a 167.0-169.0
    3-052 3,4-Cl2 CN CH2CF3 162.0-164.0
    3-053 3,4-Cl2 Ph CH2Pr-c 153.0-154.0
    3-054 3,4-Cl2 Ph CH2CF3 157.0-158.0
    3-055 3,4-Cl2 Ph CH2Ph 173.0-175.0
    3-056 3,5-Cl2 c-Pr CH2CF3 144.0-145.0
    3-057 3,5-Cl2 CF3 H 256.0-258.0
    3-058 3,5-Cl2 CF3 i-Bu 167.0-170.0
    3-059 3,5-Cl2 CF3 CH2Cl *1
    3-060 3,5-Cl2 CF3 CH2CF3  94.0-96.0
    3-061 3,5-Cl2 CF3 CH2(T-4)  84.0-87.0
    3-062 3,5-Cl2 CF3 CH2OH 254.0-260.0
    3-063 3,5-Cl2 CF3 CH2CH(OCH3)2 198.0-200.0
    3-064 3,5-Cl2 CF3 CH2CH(OEt)2 *1
    3-065 3,5-Cl2 CF3 CH2CH(CH3)OC(O)NHEt 127.0-129.0
    3-066 3,5-Cl2 CF3 CH2CH(CH3)OC(O)NH(Ph-4-F) 162.0-165.0
    3-067 3,5-Cl2 CF3 CH2CH(OH)CH2OH *1
    3-068 3,5-Cl2 CF3 CH2(E-4a) 123.5-126.0
    3-069 3,5-Cl2 CF3 CH2(E-5a) *1
    3-070 3,5-Cl2 CF3 CH2(E-10a) 152.0-153.0
    3-071 3,5-Cl2 CF3 CH2(E-10b)CH3 151.0-153.0
    3-072 3,5-Cl2 CF3 CH2(E-32a) *1
    3-073 3,5-Cl2 CF3 C(CH3)2CH2SCH3  91.0-92.0
    3-074 3,5-Cl2 CF3 C(CH3)2CH2SO2CH3 *1
    3-075 3,5-Cl2 CF3 CH2(E-18a) 124.0-126.0
    3-076 3,5-Cl2 CF3 CH2(E-18c) 253.0-255.0
    3-077 3,5-Cl2 CF3 CH2CHO *1
    3-078 3,5-Cl2 CF3 CH2CH═NOH *1
    3-079 3,5-Cl2 CF3 CH2CH═NOCH3 *1
    3-080 3,5-Cl2 CF3 CH2C(CH3)═NOCH3  71.0-75.0
    3-081 3,5-Cl2 CF3 CH2CN 145.0-151.0
    3-082 3,5-Cl2 CF3 CH2C(O)OH *1
    3-083 3,5-Cl2 CF3 CH2C(O)OCH3 *1
    3-084 3,5-Cl2 CF3 CH2C(O)NH2 100.0-107.0
    3-085 3,5-Cl2 CF3 CH2C(O)NHCH2CH2Cl 161.5-165.0
    3-086 3,5-Cl2 CF3 CH2C(O)NHCH2CF3 108.0-114.0
    3-087 3,5-Cl2 CF3 CH2C(S)NH2 *1
    3-088 3,5-Cl2 CF3 CH2C(═NOH)NH2•HCl 140.0-144.5
    3-089 3,5-Cl2 CF3 CH2CH═CH2 *1
    3-090 3,5-Cl2 CF3 CH2C(CH3)═CH2 133.0-136.0
    3-091 3,5-Cl2 CF3 CH2CCl═CH2 121.0-123.0
    3-092 3,5-Cl2 CF3 CH2CH═CCl2 118.0-120.0
    3-093 3,5-Cl2 CF3 CH2CCl═CHCl 153.0-154.0
    3-094 3,5-Cl2 CF3 CH2C≡CH 144.0-146.0
    3-095 3,5-Cl2 CF3 CH2Ph 174.0-177.0
    3-096 3,5-Cl2 CF3 CH2(Ph-4-Br) 203.0-205.0
    3-097 3,5-Cl2 CF3 CH2(Ph-4-SCH3) 182.0-184.0
    3-098 3,5-Cl2 CF3 CH2[Ph-4-S(O)CH3] 170.0-174.0
    3-099 3,5-Cl2 CF3 CH2(Ph-4-SO2CH3) 214.0-216.0
    3-100 3,5-Cl2 CF3 CH2(Ph-2-NO2) 165.0-167.0
    3-101 3,5-Cl2 CF3 CH2(D-1a) 178.5-181.0
    3-102 3,5-Cl2 CF3 CH2(D-3a) 201.0-202.0
    3-103 3,5-Cl2 CF3 CH2(D-3d)Cl 144.0-146.0
    3-104 3,5-Cl2 CF3 CH2(D-10b)Cl  87.0-95.0
    3-105 3,5-Cl2 CF3 CH2(D-15a)CH3 154.0-155.0
    3-106 3,5-Cl2 CF3 CH2(D-16b)Cl 224.0-225.0
    3-107 3,5-Cl2 CF3 CH2(D-16c)Cl *1
    3-108 3,5-Cl2 CF3 CH2(D-16d) *1
    3-109 3,5-Cl2 CF3 CH2(D-17a)CH3  59.0-61.0
    3-110 3,5-Cl2 CF3 CH2(D-17b)Cl *1
    3-111 3,5-Cl2 CF3 CH2(D-21a) 178.0-179.0
    3-112 3,5-Cl2 CF3 CH2(D-22a) 156.0-158.0
    3-113 3,5-Cl2 CF3 CH2(D-22b)Cl  94.0-96.0
    3-114 3,5-Cl2 CF3 CH2(D-22b)CH3 *1
    3-115 3,5-Cl2 CF3 CH2(D-23a) 191.0-193.0
    3-116 3,5-Cl2 CF3 CH2(D-23b)Cl 165.0-167.0
    3-117 3,5-Cl2 CF3 CH2(D-24b) 218.0-220.0
    3-118 3,5-Cl2 CF3 CH2(D-24c) *1
    3-119 3,5-Cl2 CF3 CH2(D-25a)CH3 *1
    3-120 3,5-Cl2 CF3 CH2(D-27a)CH3 *1
    3-121 3,5-Cl2 CF3 CH2(D-29b)CH3 *1
    3-122 3,5-Cl2 CF3 CH2(D-34a) *1
    3-123 3,5-Cl2 CF3 CH2(D-35a) 157.5-161.0
    3-124 3,5-Cl2 CF3 CH2(D-38a) 224.5-226.0
    3-125 3,5-Cl2 CF3 CH2(D-47a) 150.0-151.0
    3-126 3,5-Cl2 CF3 CH2(D-47c)Cl 124.0-126.0
    3-127 3,5-Cl2 CF3 CH2(D-47e)CH3 *2
    3-128 3,5-Cl2 CF3 CH2(D-47i) 121.0-124.0
    3-129 3,5-Cl2 CF3 CH2(D-48e)Cl 159.5-163.0
    3-130 3,5-Cl2 CF3 CH2(D-50d) 250.0-255.0
    3-131 3,5-Cl2 CF3 CH2(D-53b)CH3 *1
    3-132 3,5-Cl2 CF3 CH(CH3)Ph 137.5-141.0
    3-133 3,5-Cl2 CF3 C(O)(D-47a) *1
    3-134 3,5-Cl2 CF3 OCH3 *1
    3-135 3,5-Cl2 CF3 NH(D-47a) *1
    3-136 3,5-Cl2 CF3 NH(D-50a) 202.0-204.0
    3-137 3,5-Cl2 CF3 NH(D-50b)CF3 146.0-149.0
    3-138 3,5-Cl2 CF3 NH(D-54b)Cl 124.0-130.0
    3-139 3,5-Cl2 CF3 N(CH3)Ph 174.0-178.0
    3-140 3,5-Cl2 CF3 D-21a 268.0-273.0
    3-141 3-CH3-4-F CF3 CH2CF3 151.0-152.0
    3-142 3-Cl-5-CH3 CF3 CH2CF3  74.0-76.0
    3-143 3-Cl-5-CH3 CF3 CH2(D-47a) *1
    3-144 3-Cl-4-OCH3 CF3 CH2CF3 135.0-138.0
    3-145 3-CF3-5-OCH3 CF3 CH2CF3 161.0-162.0
    3-146 3-OCH2O-4 CF3 CH2CF3 149.0-151.0
    3-147 2-F-3-CH3-5-Cl CF3 CH2CF3 *1
    3-148 3,5-Cl2 CF3 CH2(D-34b)CH3 143.0-144.5
    3-149 3,5-Cl2 CF3 NH2 170.0-172.0
    3-150 3,5-Cl2 CF3 Ph-4-F 166.0-168.0
    3-151 3,5-Cl2 CF3 E-4a 210.0-213.0
  • TABLE 10
    Figure US20150105398A1-20150416-C00080
    No. (X)m R3 R2 R1 m.p. (° C.)
    4-001 3,4-Cl2 CF3 —CH2CH2CH(CH3)CH2CH2— 132.0-134.0
    4-002 3,4-Cl2 CF3 —CH2CH2CH2CH2CH2CH2— 160.0-163.0
    4-003 3,5-Cl2 CF3 CH2OCH3 CH2(D-47a) *1
    4-004 3,5-Cl2 CF3 CH2OEt CH2(D-47a) *1
    4-005 3,5-Cl2 CF3 CH2SO2CH3 CH2(D-47a) *1
    4-006 3,5-Cl2 CF3 CH2CH═CH2 CH2(D-47a) *1
    4-007 3,5-Cl2 CF3 CH(CH═CH2)CH2CH═CH2 CH2(D-47a) *1
    4-008 3,5-Cl2 CF3 CH2Ph CH2(D-47a) *1
    4-009 3,5-Cl2 CF3 C(O)OCH3 CH2(D-47a) *1
    4-010 3,5-Cl2 CF3 Et CH2(D-48e)Cl *1
    4-011 3,5-Cl2 CF3 CH3 OCH3 *1
  • TABLE 11
    Figure US20150105398A1-20150416-C00081
    No. (X)m R3 (Y)n R1 m.p. (C°)
    5-001 3-Cl CF3 2-CH3 CH2(D-47a) *1
    5-002 3-Br CF3 2-CH3 CH2CF3 158.5-161.0
    5-003 3-Br CF3 2-CH3 CH2(D-47a) *1
    5-004 3-I CF3 2-CH3 CH2CF3 168.0-172.5
    5-005 3-I CF3 2-CH3 CH2(D-47a) 135.5-138.0
    5-006 4-I CF3 2-CH3 CH2CF3 134.0-135.0
    5-007 4-I CF3 2-CH3 CH2(D-47a) *1
    5-008 3-CF3 CF3 2-CH3 CH2CF3 135.5-137.5
    5-009 3-CF3 CF3 2-CH3 CH2(D-47a) *1
    5-010 3-(T-4) CF3 2-CH3 CH2CF3 *2
    5-011 3-(T-4) CF3 2-CH3 CH2(D-47a) *2
    5-012 3-OCF3 CF3 2-CH3 CH2CF3 *2
    5-013 3-OCF3 CF3 2-CH3 CH2(D-47a) *1
    5-014 3-OCF2Br CF3 2-CH3 CH2CF3 *1
    5-015 3-OCF2Br CF3 2-CH3 CH2(D-47a) *2
    5-016 3-OCF2CHFOCF2CF2CF3 CF3 2-CH3 CH2CF3 *1
    5-017 3-OCF2CHFOCF2CF2CF3 CF3 2-CH3 CH2(D-47a) *1
    5-018 3-OCH2(Ph-2-Cl) CF3 2-CH3 CH2(D-47a) *1
    5-019 3-O[(D-47f)-3-Cl-5-CF3] CF3 2-CH3 CH2CF3 *1
    5-020 3-O[(D-47f)-3-Cl-5-CF3] CF3 2-CH3 CH2(D-47a) *1
    5-021 3-SEt CF3 2-CH3 CH2(D-47a) *1
    5-022 3-SCF3 CF3 2-CH3 CH2CF3 *1
    5-023 3-SCF3 CF3 2-CH3 CH2(D-47a) *1
    5-024 3-N(CH3)C(O)CF3 CF3 2-CH3 CH2CF3 *1
    5-025 3-N(CH3)C(O)CF3 CF3 2-CH3 CH2(D-47a) *1
    5-026 3-N(CH3)SO2CF3 CF3 2-CH3 CH2CF3 *1
    5-027 3-N(CH3)SO2CF3 CF3 2-CH3 CH2(D-47a) *1
    5-028 3-Ph CF3 2-CH3 CH2(D-47a) *1
    5-029 3,5-F2 CF3 2-CH3 CH2(D-47a) *1
    5-030 3,5-Cl2 CH3 2-CH3 CH2CF3 *1
    5-031 3,5-Cl2 i-Pr 2-CH3 CH2CF3 *1
    5-032 3,5-Cl2 c-Pr 2-CH3 CH2CF3 157.0-158.0
    5-033 3,5-Cl2 c-Pr 2-CH3 CH2(D-47a) *1
    5-034 3,5-Cl2 CH2Cl 2-CH3 CH2CF3 117.0-119.0
    5-035 3,5-Cl2 CH2Cl 2-CH3 CH2(D-47a) *1
    5-036 3,5-Cl2 CHF2 2-CH3 CH2CF3  94.0-97.5
    5-037 3,5-Cl2 CHF2 2-CH3 CH2(D-47a) *1
    5-038 3,5-Cl2 CF3 2-F CH2CF3 *1
    5-039 3,5-Cl2 CF3 2-F CH2Ph 172.0-176.0
    5-040 3,5-Cl2 CF3 2-F CH2(D-22a) *1
    5-041 3,5-Cl2 CF3 2-F CH2(D-47a) 126.0-129.0
    5-042 3,5-Cl2 CF3 3-F CH2CF3 *1
    5-043 3,5-Cl2 CF3 3-F CH2Ph 178.0-181.0
    5-044 3,5-Cl2 CF3 3-F CH2(D-47a) 125.0-127.0
    5-045 3,5-Cl2 CF3 2-Cl CH2Pr-c 132.0-134.0
    5-046 3,5-Cl2 CF3 2-Cl CH2CF3 124.0-125.0
    5-047 3,5-Cl2 CF3 2-Cl CH2Ph  57.0-58.0
    5-048 3,5-Cl2 CF3 2-Cl CH2(Ph-4-NO2) *1
    5-049 3,5-Cl2 CF3 2-Cl CH2(D-21a) *1
    5-050 3,5-Cl2 CF3 2-Cl CH2(D-22a) *1
    5-051 3,5-Cl2 CF3 2-Cl CH2(D-22b)Cl *2
    5-052 3,5-Cl2 CF3 2-Cl CH2(D-28a) *1
    5-053 3,5-Cl2 CF3 2-Cl CH2(D-47a) *1
    5-054 3,5-Cl2 CF3 3-Cl CH2CF3 149.0-150.0
    5-055 3,5-Cl2 CF3 3-Cl CH2Ph 119.0-121.0
    5-056 3,5-Cl2 CF3 3-Cl CH2(D-47a) *1
    5-057 3,5-Cl2 CF3 2-Br CH2CF3 145.0-147.0
    5-058 3,5-Cl2 CF3 2-Br CH2(D-47a) *1
    5-059 3,5-Cl2 CF3 2-I CH2CF3 128.0-130.0
    5-060 3,5-Cl2 CF3 2-I CH2CH2OEt *1
    5-061 3,5-Cl2 CF3 2-I CH2CH(OCH3)2 *1
    5-062 3,5-Cl2 CF3 2-I CH2C(O)NHCH3 *1
    5-063 3,5-Cl2 CF3 2-I CH2C(O)NHCH2CH2Cl  68.0-70.0
    5-064 3,5-Cl2 CF3 2-I CH2CH═CH2  97.0-100.0
    5-065 3,5-Cl2 CF3 2-I CH2(D-47a) *1
    5-066 3,5-Cl2 CF3 2-CH3 H 162.0-164.0
    5-067 3,5-Cl2 CF3 2-CH3 Et 129.5-133.0
    5-068 3,5-Cl2 CF3 2-CH3 c-Pr  84.0-86.0
    5-069 3,5-Cl2 CF3 2-CH3 i-Bu 138.0-140.0
    5-070 3,5-Cl2 CF3 2-CH3 CH2Pr-c *1
    5-071 3,5-Cl2 CF3 2-CH3 c-Bu 139.0-141.0
    5-072 3,5-Cl2 CF3 2-CH3 CH2Bu-c *1
    5-073 3,5-Cl2 CF3 2-CH3 c-Pen 155.0-158.0
    5-074 3,5-Cl2 CF3 2-CH3 CH2CH2Cl 161.5-164.5
    5-075 3,5-Cl2 CF3 2-CH3 CH2CF3 155.5-157.0
    5-075(+) 99% e.e. [α]D 23.0 +74.38° (EtOH, c = 0.621) *1
    5-075(−) 99% e.e. [α]D 22.8 −70.98° (EtOH, c = 0.648) *1
    5-076 3,5-Cl2 CF3 2-CH3 CH2CH2OCH3 115.0-117.0
    5-077 3,5-Cl2 CF3 2-CH3 CH2CH2OEt *1
    5-078 3,5-Cl2 CF3 2-CH3 CH2CH2OCH2CH2Cl 140.0-142.0
    5-079 3,5-Cl2 CF3 2-CH3 CH2CH2OC(O)CH3 *2
    5-080 3,5-Cl2 CF3 2-CH3 CH2CH2OC(O)NHEt *2
    5-081 3,5-Cl2 CF3 2-CH3 CH2CH(CH3)OH  67.0-70.0
    5-082 3,5-Cl2 CF3 2-CH3 CH2CH(CH3)OCH3 179.0-181.0
    5-083 3,5-Cl2 CF3 2-CH3 CH2CH(OCH3)2 *1
    5-084 3,5-Cl2 CF3 2-CH3 CH2CH(OEt)2 *2
    5-085 3,5-Cl2 CF3 2-CH3 CH(CH3)CH2OC(O)NHEt *1
    5-086 3,5-Cl2 CF3 2-CH3 CH2(E-4a) *1
    5-087 3,5-Cl2 CF3 2-CH3 CH2(E-5a) *2
    5-088 3,5-Cl2 CF3 2-CH3 CH2(E-10a) 158.5-160.5
    5-089 3,5-Cl2 CF3 2-CH3 CH2(E-10b)CH3 153.0-154.0
    5-090 3,5-Cl2 CF3 2-CH3 CH2(E-32a) *1
    5-091 3,5-Cl2 CF3 2-CH3 CH2CH2SCH3 121.0-127.0
    5-092 3,5-Cl2 CF3 2-CH3 CH2CH2S(O)CH3 *1
    5-093 3,5-Cl2 CF3 2-CH3 CH2CH2SEt 106.0-109.0
    5-094 3,5-Cl2 CF3 2-CH3 CH2CH2SO2Et *1
    5-095 3,5-Cl2 CF3 2-CH3 CH2CH2SCH2Ph *1
    5-096 3,5-Cl2 CF3 2-CH3 CH2CH2SO2CH2Ph *1
    5-097 3,5-Cl2 CF3 2-CH3 CH2CH2SCH2(D-1a) *1
    5-098 3,5-Cl2 CF3 2-CH3 CH2CH2SO2CH2(D-1a) *1
    5-099 3,5-Cl2 CF3 2-CH3 CH2CH(CH3)SCH3 *1
    5-100 3,5-Cl2 CF3 2-CH3 CH2CH(CH3)S(O)CH3 *1
    5-101 3,5-Cl2 CF3 2-CH3 CH2CH(CH3)SO2CH3 *1
    5-102 3,5-Cl2 CF3 2-CH3 CH(CH3)CH2SCH3 *1
    5-103 3,5-Cl2 CF3 2-CH3 CH(CH3)CH2SO2CH3 *1
    5-104 3,5-Cl2 CF3 2-CH3 C(CH3)2CH2SCH3 *1
    5-105 3,5-Cl2 CF3 2-CH3 C(CH3)2CH2SO2CH3 167.0-169.0
    5-106 3,5-Cl2 CF3 2-CH3 CH2(E-18a) 204.0-206.0
    5-107 3,5-Cl2 CF3 2-CH3 CH2(E-18c) 249.0-251.0
    5-108 3,5-Cl2 CF3 2-CH3 CH2(E-43a) 199.0-201.0
    5-109 3,5-Cl2 CF3 2-CH3 CH2CH2NHC(O)CF3  81.0-84.0
    5-110 3,5-Cl2 CF3 2-CH3 CH2CH2NHC(O)CH2CF3 143.0-146.0
    5-111 3,5-Cl2 CF3 2-CH3 CH2C(O)CH3 155.0-160.0
    5-112 3,5-Cl2 CF3 2-CH3 CH2CH═NOH *1
    5-113 3,5-Cl2 CF3 2-CH3 CH2CH═NOCH3 *2
    5-114 3,5-Cl2 CF3 2-CH3 CH2CH═NOCH2Pr-c *1
    5-115 3,5-Cl2 CF3 2-CH3 CH2CH═NOCH2(Ph-4-Cl) *2
    5-116 3,5-Cl2 CF3 2-CH3 CH2CH═NOCH2CH2-TMS *1
    5-117 3,5-Cl2 CF3 2-CH3 CH2C(CH3)═NOCH3 101.0-105.0
    5-118 3,5-Cl2 CF3 2-CH3 CH2(M-5a)CH3 *1
    5-119 3,5-Cl2 CF3 2-CH3 CH2CN 186.5-189.0
    5-120 3,5-Cl2 CF3 2-CH3 CH(OCH2CF3)CN *1
    5-121 3,5-Cl2 CF3 2-CH3 CH(Ph)CN 165.5-167.0
    5-122 3,5-Cl2 CF3 2-CH3 CH(D-1a)CN *1
    5-123 3,5-Cl2 CF3 2-CH3 CH(D-3a)CN *1
    5-124 3,5-Cl2 CF3 2-CH3 CH(D-14a)CN 192.0-194.5
    5-125 3,5-Cl2 CF3 2-CH3 CH(D-38a)CN 185.0-189.5
    5-126 3,5-Cl2 CF3 2-CH3 CH(D-47a)CN *1
    5-127 3,5-Cl2 CF3 2-CH3 CH2C(O)OH 195.0-197.0
    5-128 3,5-Cl2 CF3 2-CH3 CH2C(O)OCH3 *2
    5-129 3,5-Cl2 CF3 2-CH3 CH2C(O)OCH2CF3 157.0-158.0
    5-130 3,5-Cl2 CF3 2-CH3 CH(CH3)C(O)OCH3(D) *1
    5-131 3,5-Cl2 CF3 2-CH3 CH(CH3)C(O)OEt(L) *1
    5-132 3,5-Cl2 CF3 2-CH3 CH(CH3)C(O)OCH2CF3 *1
    5-133 3,5-Cl2 CF3 2-CH3 CH(OH)C(O)OCH3 *1
    5-134 3,5-Cl2 CF3 2-CH3 CH(OCH3)C(O)OCH3 *1
    5-135 3,5-Cl2 CF3 2-CH3 CH(D-14a)C(O)OCH3  93.5-97.0
    5-136 3,5-Cl2 CF3 2-CH3 CH2CH2C(O)OEt *1
    5-137 3,5-Cl2 CF3 2-CH3 CH2C(O)NH2  87.0-91.0
    5-138 3,5-Cl2 CF3 2-CH3 CH2C(O)NHCH3 *1
    5-139 3,5-Cl2 CF3 2-CH3 CH2C(O)N(CH3)2 *1
    5-140 3,5-Cl2 CF3 2-CH3 CH2C(O)NHEt 137.5-141.0
    5-141 3,5-Cl2 CF3 2-CH3 CH2C(O)NHPr-n *1
    5-142 3,5-Cl2 CF3 2-CH3 CH2C(O)NHPr-i 152.0-155.0
    5-143 3,5-Cl2 CF3 2-CH3 CH2C(O)NHBu-i *1
    5-144 3,5-Cl2 CF3 2-CH3 CH2C(O)NHBu-c 174.0-177.0
    5-145 3,5-Cl2 CF3 2-CH3 CH2C(O)NHBu-t *1
    5-146 3,5-Cl2 CF3 2-CH3 CH2C(O)NHCH2Bu-t *1
    5-147 3,5-Cl2 CF3 2-CH3 CH2C(O)NHCH2CH2F *1
    5-148 3,5-Cl2 CF3 2-CH3 CH2C(O)NHCH2CH2Cl 109.0-112.0
    5-149 3,5-Cl2 CF3 2-CH3 CH2C(O)N(CH3)CH2CH2Cl *2
    5-150 3,5-Cl2 CF3 2-CH3 CH2C(O)NHCH2CH2Br *1
    5-151 3,5-Cl2 CF3 2-CH3 CH2C(O)NHCH2CF3 173.5-175.5
    5-151(+) 99% e.e. [α]D 23.1 +61.96° (EtOH, c = 1.098) *1
    5-151(−) 99% e.e. [α]D 23.1 −58.95° (EtOH, c = 1.153) *1
    5-152 3,5-Cl2 CF3 2-CH3 CH2C(O)NHCH2CH2CH2Cl *1
    5-153 3,5-Cl2 CF3 2-CH3 CH2C(O)NHCH2(T-4) *1
    5-154 3,5-Cl2 CF3 2-CH3 CH2C(O)NHCH2CH2OH *1
    5-155 3,5-Cl2 CF3 2-CH3 CH2C(O)N(CH3)CH2CH2OH *1
    5-156 3,5-Cl2 CF3 2-CH3 CH2C(O)NHCH2CH2OCH3 146.0-149.0
    5-157 3,5-Cl2 CF3 2-CH3 CH2C(O)NHCH2CH2OEt *1
    5-158 3,5-Cl2 CF3 2-CH3 CH2C(O)NHCH2CH2SCH3 138.0-143.0
    5-159 3,5-Cl2 CF3 2-CH3 CH2C(O)NHCH2CH2SO2CH3 *1
    5-160 3,5-Cl2 CF3 2-CH3 CH2C(O)NHCH2CH═CH2  76.0-79.0
    5-161 3,5-Cl2 CF3 2-CH3 CH2C(O)N(CH3)CH2CH═CH2 *1
    5-162 3,5-Cl2 CF3 2-CH3 CH2C(O)N(CH2CH═CH2)2 *1
    5-163 3,5-Cl2 CF3 2-CH3 CH2C(O)NHCH2CCl═CH2 *1
    5-164 3,5-Cl2 CF3 2-CH3 CH2C(O)NHCH2CH═CCl2 188.0-192.0
    5-165 3,5-Cl2 CF3 2-CH3 CH2C(O)NHCH2C≡CH *1
    5-166 3,5-Cl2 CF3 2-CH3 CH2C(O)NHCH2Ph 187.0-191.0
    5-167 3,5-Cl2 CF3 2-CH3 CH2C(O)NHCH2(D-22a) *1
    5-168 3,5-Cl2 CF3 2-CH3 CH2C(O)NHCH2(D-47a) *1
    5-169 3,5-Cl2 CF3 2-CH3 CH2C(O)NHPh 181.0-183.0
    5-170 3,5-Cl2 CF3 2-CH3 CH2C(O)(T-37) 118.0-121.0
    5-171 3,5-Cl2 CF3 2-CH3 CH2C(O)(T-40) *1
    5-172 3,5-Cl2 CF3 2-CH3 CH2C(O)NHNHCH2CF3 118.0-120.0
    5-173 3,5-Cl2 CF3 2-CH3 CH2C(O)NHN(CH3)Ph *1
    5-174 3,5-Cl2 CF3 2-CH3 CH(CH3)C(O)NHCH2CH2Cl 146.0-149.0
    5-175 3,5-Cl2 CF3 2-CH3 CH(Ph)C(O)NHCH3(R) 118.0-121.0
    5-176 3,5-Cl2 CF3 2-CH3 CH(Ph)C(O)NHCH3(S) *1
    5-177 3,5-Cl2 CF3 2-CH3 CH2CH2C(O)NHCH2CH2Cl 153.0-157.0
    5-178 3,5-Cl2 CF3 2-CH3 CH2(T-22) *1
    5-179 3,5-Cl2 CF3 2-CH3 CH2C(S)NH2 *1
    5-180 3,5-Cl2 CF3 2-CH3 CH(Ph)C(S)NH2 *1
    5-181 3,5-Cl2 CF3 2-CH3 CH2Si(CH3)3 *1
    5-182 3,5-Cl2 CF3 2-CH3 CH2CH═CH2 *1
    5-183 3,5-Cl2 CF3 2-CH3 CH2CCl═CH2 *1
    5-184 3,5-Cl2 CF3 2-CH3 CH2CH═CCl2 *1
    5-185 3,5-Cl2 CF3 2-CH3 CH2CCl═CHCl *1
    5-186 3,5-Cl2 CF3 2-CH3 CH2C≡CH *1
    5-187 3,5-Cl2 CF3 2-CH3 CH2Ph 142.0-144.5
    5-188 3,5-Cl2 CF3 2-CH3 CH(CH3)Ph 121.5-123.5
    5-189 3,5-Cl2 CF3 2-CH3 CH(CH3)Ph(R) *1
    5-189(+) 99% d.e. [α]D 22.9 +59.13° (EtOH, c = 0.262) *1
    5-189(−) 99% d.e. [α]D 23.0 −86.72° (EtOH, c = 0.250) *1
    5-190 3,5-Cl2 CF3 2-CH3 CH(CH3)Ph(S) *1
    5-190(+) 99% d.e. [α]D 23.0 +89.06° (EtOH, c = 0.466) *1
    5-190(−) 99% d.e. [α]D 23.0 −117.66° (EtOH, c = 0.322) *1
    5-191 3,5-Cl2 CF3 2-CH3 CH(Et)Ph *1
    5-192 3,5-Cl2 CF3 2-CH3 C(CH3)2Ph  91.0-93.5
    5-193 3,5-Cl2 CF3 2-CH3 CH(CF3)Ph 175.5-180.0
    5-194 3,5-Cl2 CF3 2-CH3 CH(OEt)Ph *2
    5-195 3,5-Cl2 CF3 2-CH3 CH2(Ph-2-F) 151.0-153.0
    5-196 3,5-Cl2 CF3 2-CH3 CH2(Ph-3-F) 134.0-136.0
    5-197 3,5-Cl2 CF3 2-CH3 CH2(Ph-4-F) 153.0-155.0
    5-198 3,5-Cl2 CF3 2-CH3 CH2(Ph-2-Cl) 147.0-149.0
    5-199 3,5-Cl2 CF3 2-CH3 CH2(Ph-3-Cl) 160.0-162.0
    5-200 3,5-Cl2 CF3 2-CH3 CH2(Ph-4-Cl) 164.0-166.0
    5-201 3,5-Cl2 CF3 2-CH3 CH2(Ph-3-NO2) 198.0-200.0
    5-202 3,5-Cl2 CF3 2-CH3 CH2(Ph-4-NO2) 204.0-206.0
    5-203 3,5-Cl2 CF3 2-CH3 CH2(Ph-2,5-F2) 153.0-155.0
    5-204 3,5-Cl2 CF3 2-CH3 CH2(Ph-3,5-F2) 146.0-149.0
    5-205 3,5-Cl2 CF3 2-CH3 CH2(D-1a) *1
    5-206 3,5-Cl2 CF3 2-CH3 CH2(D-3a) 147.0-148.5
    5-207 3,5-Cl2 CF3 2-CH3 CH2(D-3d)Cl *1
    5-208 3,5-Cl2 CF3 2-CH3 CH2(D-8b)CH3 *1
    5-209 3,5-Cl2 CF3 2-CH3 CH2(D-10b)Cl *1
    5-210 3,5-Cl2 CF3 2-CH3 CH2(D-15a)CH3 147.0-148.0
    5-211 3,5-Cl2 CF3 2-CH3 CH2(D-16b)Cl 237.0-238.0
    5-212 3,5-Cl2 CF3 2-CH3 CH2(D-16c)Cl *1
    5-213 3,5-Cl2 CF3 2-CH3 CH2(D-16d) *1
    5-214 3,5-Cl2 CF3 2-CH3 CH2(D-17a)CH3  76.0-77.0
    5-215 3,5-Cl2 CF3 2-CH3 CH2(D-17b)Cl 157.0-158.0
    5-216 3,5-Cl2 CF3 2-CH3 CH2(D-21a) *1
    5-217 3,5-Cl2 CF3 2-CH3 CH(Ph)(D-21a) *1
    5-218 3,5-Cl2 CF3 2-CH3 CH2(D-21b)CF3 *1
    5-219 3,5-Cl2 CF3 2-CH3 CH2(D-22a) 135.0-136.5
    5-219(+) 97% e.e. [α]D 22.6 +56.54° (EtOH, c = 0.384) *1
    5-219(−) 99% e.e. [α]D 22.4 −58.65° (EtOH, c = 0.393) *1
    5-220 3,5-Cl2 CF3 2-CH3 CH2(D-22b)Cl *1
    5-221 3,5-Cl2 CF3 2-CH3 CH2(D-22b)CH3 *1
    5-222 3,5-Cl2 CF3 2-CH3 CH2(D-23a) *1
    5-223 3,5-Cl2 CF3 2-CH3 CH2(D-23b)Cl *1
    5-224 3,5-Cl2 CF3 2-CH3 CH2(D-25a)CH3 *1
    5-225 3,5-Cl2 CF3 2-CH3 CH2(D-27a)CH3 *1
    5-226 3,5-Cl2 CF3 2-CH3 CH2(D-28a) *1
    5-227 3,5-Cl2 CF3 2-CH3 CH2(D-29b)CH3 *1
    5-228 3,5-Cl2 CF3 2-CH3 CH2(D-30a) 120.0-123.5
    5-229 3,5-Cl2 CF3 2-CH3 CH2(D-31a) 122.0-125.0
    5-230 3,5-Cl2 CF3 2-CH3 CH2(D-34a) *1
    5-231 3,5-Cl2 CF3 2-CH3 CH2(D-34b)CH3 *1
    5-232 3,5-Cl2 CF3 2-CH3 CH2(D-35a) *1
    5-233 3,5-Cl2 CF3 2-CH3 CH2(D-38a) *1
    5-234 3,5-Cl2 CF3 2-CH3 CH2(D-47a) 131.0-135.5
    5-235 3,5-Cl2 CF3 2-CH3 CH(CH3)(D-47a) *1
    5-236 3,5-Cl2 CF3 2-CH3 CH2(D-47c)Cl 164.0-166.0
    5-237 3,5-Cl2 CF3 2-CH3 CH2(D-47c)NO2 129.0-131.0
    5-238 3,5-Cl2 CF3 2-CH3 CH2(D-47e)Cl *1
    5-239 3,5-Cl2 CF3 2-CH3 CH2(D-47i) *1
    5-240 3,5-Cl2 CF3 2-CH3 CH2(D-48a) *1
    5-241 3,5-Cl2 CF3 2-CH3 CH2(D-48e)Cl 200.5-202.0
    5-242 3,5-Cl2 CF3 2-CH3 CH2(D-49a) *1
    5-243 3,5-Cl2 CF3 2-CH3 CH2(D-50a) *1
    5-244 3,5-Cl2 CF3 2-CH3 CH2[(D-50d)-4,6-(OCH3)2]  58.0-65.0
    5-245 3,5-Cl2 CF3 2-CH3 CH2(D-51a) *1
    5-246 3,5-Cl2 CF3 2-CH3 CH2(D-53a) *1
    5-247 3,5-Cl2 CF3 2-CH3 CH2(D-53b)CH3 *1
    5-248 3,5-Cl2 CF3 2-CH3 NH2  87.0-89.0
    5-249 3,5-Cl2 CF3 2-CH3 N(CH3)2  79.0-84.0
    5-250 3,5-Cl2 CF3 2-CH3 NHBu-t  71.0-76.0
    5-251 3,5-Cl2 CF3 2-CH3 NHCH2CF3 158.0-159.0
    5-252 3,5-Cl2 CF3 2-CH3 NHCH2CH2OH  61.0-70.0
    5-253 3,5-Cl2 CF3 2-CH3 T-34a  59.0-63.0
    5-254 3,5-Cl2 CF3 2-CH3 T-40  95.0-105.0
    5-255 3,5-Cl2 CF3 2-CH3 T-42 155.0-157.0
    5-256 3,5-Cl2 CF3 2-CH3 NHC(O)CH3 117.0-118.0
    5-257 3,5-Cl2 CF3 2-CH3 N(Ph)C(O)CH3  89.0-99.0
    5-258 3,5-Cl2 CF3 2-CH3 NHC(O)Pr-n 109.0-111.0
    5-259 3,5-Cl2 CF3 2-CH3 NHC(O)CH2CH2Cl 109.0-110.0
    5-260 3,5-Cl2 CF3 2-CH3 NHC(O)CH2CN 121.0-125.0
    5-261 3,5-Cl2 CF3 2-CH3 NHC(O)OCH3  86.0-93.0
    5-262 3,5-Cl2 CF3 2-CH3 N(CH3)C(O)OCH3 131.0-132.0
    5-263 3,5-Cl2 CF3 2-CH3 N(Ph)C(O)OCH3  98.0-106.0
    5-264 3,5-Cl2 CF3 2-CH3 NHC(O)OEt  75.0-84.0
    5-265 3,5-Cl2 CF3 2-CH3 NHC(O)OBu-t *1
    5-266 3,5-Cl2 CF3 2-CH3 NHC(O)OCH2Ph 155.0-156.0
    5-267 3,5-Cl2 CF3 2-CH3 NHC(O)NHPh 212.0-214.0
    5-268 3,5-Cl2 CF3 2-CH3 NHC(O)Ph 213.0-214.0
    5-269 3,5-Cl2 CF3 2-CH3 NHC(O)(D-1a) 230.0-232.0
    5-270 3,5-Cl2 CF3 2-CH3 NHC(O)(D-47a) 116.0-117.0
    5-271 3,5-Cl2 CF3 2-CH3 NHC(S)NHCH3 143.0-145.0
    5-272 3,5-Cl2 CF3 2-CH3 NHC(S)N(CH3)2 179.0-182.0
    5-273 3,5-Cl2 CF3 2-CH3 NHPh  88.0-96.0
    5-274 3,5-Cl2 CF3 2-CH3 N(CH3)Ph 158.0-160.0
    5-275 3,5-Cl2 CF3 2-CH3 N(CH2CH═CH2)Ph  78.0-86.0
    5-276 3,5-Cl2 CF3 2-CH3 N(CH2Ph)Ph  58.0-60.0
    5-277 3,5-Cl2 CF3 2-CH3 NH(Ph-2-Cl) *1
    5-278 3,5-Cl2 CF3 2-CH3 NH(Ph-3-Cl) *1
    5-279 3,5-Cl2 CF3 2-CH3 NH(Ph-4-Cl) *1
    5-280 3,5-Cl2 CF3 2-CH3 NH(Ph-4-CF3) *1
    5-281 3,5-Cl2 CF3 2-CH3 NH(Ph-2-NO2)  89.0-95.0
    5-282 3,5-Cl2 CF3 2-CH3 NH(Ph-3-NO2) 104.0-109.0
    5-283 3,5-Cl2 CF3 2-CH3 NH(Ph-4-NO2) 120.0-126.0
    5-284 3,5-Cl2 CF3 2-CH3 N(CH3)(D-21a) 181.0-185.0
    5-285 3,5-Cl2 CF3 2-CH3 NH(D-47a) 213.0-217.0
    5-286 3,5-Cl2 CF3 2-CH3 N(CH3)(D-47a) 202.0-203.0
    5-287 3,5-Cl2 CF3 2-CH3 NH(D-47b)Cl 102.0-103.0
    5-288 3,5-Cl2 CF3 2-CH3 NH(D-47d)Cl  91.0-92.0
    5-289 3,5-Cl2 CF3 2-CH3 NH(D-47e)Cl  89.0-90.0
    5-290 3,5-Cl2 CF3 2-CH3 NH[(D-47f)-3-Cl-5-CF3] 137.0-140.0
    5-291 3,5-Cl2 CF3 2-CH3 NH(D-50a) 209.0-211.0
    5-292 3,5-Cl2 CF3 2-CH3 NH(D-50b)CF3  95.0-100.0
    5-293 3,5-Cl2 CF3 2-CH3 NH[(D-50d)-4,6-(OCH3)2]  91.0-98.0
    5-294 3,5-Cl2 CF3 2-CH3 N(CH3)(D-50a) 194.0-196.0
    5-295 3,5-Cl2 CF3 2-CH3 N(Et)(D-50a)  60.0-67.0
    5-296 3,5-Cl2 CF3 2-CH3 NH(D-51b)SCH3 *1
    5-297 3,5-Cl2 CF3 2-CH3 NH(D-51b)S(O)CH3 156.0-162.0
    5-298 3,5-Cl2 CF3 2-CH3 NH(D-51b)SO2CH3 147.0-151.0
    5-299 3,5-Cl2 CF3 2-CH3 NH(D-51c)Cl *1
    5-300 3,5-Cl2 CF3 2-CH3 NH(D-53a) 111.0-112.0
    5-301 3,5-Cl2 CF3 2-CH3 NH(D-54b)Cl *1
    5-302 3,5-Cl2 CF3 2-CH3 N═C(CH3)Ph 134.0-135.0
    5-303 3,5-Cl2 CF3 2-CH3 N═CH(D-47a) *1
    5-304 3,5-Cl2 CF3 2-CH3 T-47 146.0-148.0
    5-305 3,5-Cl2 CF3 2-CH3 D-8a 127.5-129.0
    5-306 3,5-Cl2 CF3 2-CH3 (D-13b)CH3 271.0-275.0
    5-307 3,5-Cl2 CF3 2-CH3 D-21a 281.0-284.0
    5-308 3,5-Cl2 CF3 2-CH3 D-48a 188.0-190.0
    5-309 3,5-Cl2 CF3 2-CH3 D-50a  98.0-100.0
    5-310 3,5-Cl2 CF3 2-CH3 D-51a  90.0-91.0
    5-311 3,5-Cl2 CF3 3-CH3 CH2CF3 *1
    5-312 3,5-Cl2 CF3 2-Et CH2CF3 *1
    5-313 3,5-Cl2 CF3 2-Et CH2(D-47a) *1
    5-314 3,5-Cl2 CF3 2-CF3 CH2CF3  70.0-72.0
    5-315 3,5-Cl2 CF3 2-CF3 CH2(D-47a)  69.0-70.0
    5-316 3,5-Cl2 CF3 2-CH2OH CH2CF3 *1
    5-317 3,5-Cl2 CF3 2-OCH3 CH2CF3 *1
    5-318 3,5-Cl2 CF3 2-OCH3 CH2Ph *1
    5-319 3,5-Cl2 CF3 2-OCH3 CH2(D-47a) 173.5-176.0
    5-320 3,5-Cl2 CF3 2-OCF3 CH2CF3 *2
    5-321 3,5-Cl2 CF3 2-OCF3 CH2(D-47a) 145.0-148.5
    5-322 3,5-Cl2 CF3 2-SCH3 CH2CF3 *2
    5-323 3,5-Cl2 CF3 2-SCH3 CH2(D-47a) *2
    5-324 3,5-Cl2 CF3 2-S(O)CH3 CH2CF3 *2
    5-325 3,5-Cl2 CF3 2-S(O)CH3 CH2(D-47a) *1
    5-326 3,5-Cl2 CF3 2-SO2CH3 CH2CF3 *1
    5-327 3,5-Cl2 CF3 2-SO2CH3 CH2(D-47a) 120.0-121.0
    5-328 3,5-Cl2 CF3 2-S(O)CH2Cl CH2CF3 *2
    5-329 3,5-Cl2 CF3 2-NH2 CH2CF3  78.0-79.0
    5-330 3,5-Cl2 CF3 2-NH2 CH2(D-47a) *2
    5-331 3,5-Cl2 CF3 2-NHCH3 CH2CF3 156.0-158.0
    5-332 3,5-Cl2 CF3 2-NHCH3 CH2(D-47a) *1
    5-333 3,5-Cl2 CF3 2-NHC(O)CH3 CH2CF3 *2
    5-334 3,5-Cl2 CF3 2-N(CH3)2 CH2CF3 *2
    5-335 3,5-Cl2 CF3 2-N(CH3)2 CH2(D-47a) *1
    5-336 3,5-Cl2 CF3 2-N(CH3)CHO CH2(D-47a) *1
    5-337 3,5-Cl2 CF3 2-N(CH3)C(O)CH3 CH2(D-47a) *1
    5-338 3,5-Cl2 CF3 2-NO2 CH2CF3 180.0-181.0
    5-339 3,5-Cl2 CF3 2-NO2 CH2(D-47a) *2
    5-340 3,5-Cl2 CF3 2-CN CH2CF3 *1
    5-341 3,5-Cl2 CF3 2-CN CH2(D-47a) *1
    5-342 3,5-Cl2 CF3 2-C≡C-TMS CH2CF3 *1
    5-343 3,5-Cl2 CF3 2-Ph CH2CF3 *1
    5-344 3,5-Cl2 CF3 2-Ph CH2(D-47a) 194.0-198.0
    5-345 3,5-Cl2 CF3 2-(D-38a) CH2(D-47a) *2
    5-346 3,5-Cl2 CF3 2,3-F2 CH2CF3 *1
    5-347 3,5-Cl2 CF3 2,3-F2 CH2Ph *1
    5-348 3,5-Cl2 CF3 2,3-F2 CH2(D-47a) *1
    5-349 3,5-Cl2 CF3 2,6-F2 CH2CF3 140.0-141.0
    5-350 3,5-Cl2 CF3 2,6-Cl2 CH2(D-47a) 131.0-132.0
    5-351 3,5-Cl2 CF3 2,6-(CH3)2 CH2CF3 125.0-129.0
    5-352 3,5-Cl2 CF3 2,6-(CH3)2 CH2(D-47a) *1
    5-353 3,5-Cl2 CF2Cl 2-Cl CH2(D-22a) *1
    5-354 3,5-Cl2 CF2Cl 2-Cl CH2(D-47a) *1
    5-355 3,5-Cl2 CF2Cl 2-CH3 CH2CF3 *1
    5-356 3,5-Cl2 CF2Cl 2-CH3 CH2CH2OEt *1
    5-357 3,5-Cl2 CF2Cl 2-CH3 CH2CH(OCH3)2 *1
    5-358 3,5-Cl2 CF2Cl 2-CH3 CH2CH═CH2 *1
    5-359 3,5-Cl2 CF2Cl 2-CH3 CH2(D-22a) *1
    5-360 3,5-Cl2 CF2Cl 2-CH3 CH2(D-47a) *1
    5-361 3,5-Cl2 CF2CF3 2-CH3 CH2CF3 *1
    5-362 3,5-Cl2 CF2CF3 2-CH3 CH2(D-47a) *1
    5-363 3,5-Cl2 CF2CF3 2-CH3 C(O)(D-47a) *1
    5-364 3,5-Cl2 CH2OCH2CF3 2-CH3 CH2CF3 *1
    5-365 3,5-Cl2 CH2OCH2CF3 2-CH3 CH2(D-47a) *1
    5-366 3,5-Cl2 CF2SCH3 2-CH3 CH2CF3 *2
    5-367 3,5-Cl2 CF2SCH3 2-CH3 CH2(D-47a)  51.0-52.0
    5-368 3,5-Cl2 CH2-TMS 2-CH3 CH2CF3 *1
    5-369 3,5-Cl2 CH2-TMS 2-CH3 CH2(D-47a) *1
    5-370 3,5-Cl2 TMS 2-CH3 CH2CF3 *1
    5-371 3,5-Cl2 TMS 2-CH3 CH2(D-47a) *1
    5-372 3,5-Cl2 D-47a 2-CH3 CH2CF3 *1
    5-373 3,5-Cl2 D-47a 2-CH3 CH2(D-47a) *1
    5-374 3-Cl-5-Br CF3 2-CH3 CH2CF3 *1
    5-375 3-Cl-5-Br CF3 2-CH3 CH2(D-47a) *1
    5-376 3,5-Br2 CF3 2-Cl CH2(D-22a)  63.0-64.0
    5-377 3,5-Br2 CF3 2-Cl CH2(D-47a) *2
    5-378 3,5-Br2 CF3 2-CH3 CH2CF3 *1
    5-379 3,5-Br2 CF3 2-CH3 CH2CH2OCH3 *2
    5-380 3,5-Br2 CF3 2-CH3 CH2CH2OEt *2
    5-381 3,5-Br2 CF3 2-CH3 CH2CH(OCH3)2 *2
    5-382 3,5-Br2 CF3 2-CH3 CH2C(O)OCH3 *2
    5-383 3,5-Br2 CF3 2-CH3 CH2C(O)NHCH2CH2Cl  69.0-70.0
    5-384 3,5-Br2 CF3 2-CH3 CH2C(O)NHCH2CF3 173.0-175.0
    5-385 3,5-Br2 CF3 2-CH3 CH2CH═CH2 *2
    5-386 3,5-Br2 CF3 2-CH3 CH2(D-22a) *1
    5-387 3,5-Br2 CF3 2-CH3 CH2(D-47a) *1
    5-388 3-Cl-5-CH3 CF3 2-CH3 CH2(D-47a) *2
    5-389 3,5-(CF3)2 CF3 2-CH3 CH2CF3 *1
    5-390 3,5-(CF3)2 CF3 2-CH3 CH2(D-47a) *1
    5-391 3-F-5-SCH3 CF3 2-CH3 CH2(D-47a) *1
    5-392 3-Cl-5-SCH3 CF3 2-SCH3 CH2(D-47a) *2
    5-393 3-CF3-5-OCH3 CF3 2-CH3 CH2(D-47a) *1
    5-394 3,5-(SCH3)2 CF3 2-CH3 CH2(D-47a) *1
    5-395 3-CF3-5-CN CF3 2-CH3 CH2CF3  72.0-73.0
    5-396 3-CF3-5-CN CF3 2-CH3 CH2(D-47a)  63.0-64.0
    5-397 3,4,5-Cl3 CF3 2-CH3 CH2CF3 194.0-197.0
    5-398 3,4,5-Cl3 CF3 2-CH3 CH2(D-47a) *1
    5-399 3,5-Cl2 CF3 2-CH3 CH2CH2CF3 *1
    5-400 3,5-Cl2 CF3 2-CH3 CH(CF3)OH *1
    5-401 3,5-Cl2 CF3 2-CH3 CH(CF3)OCH3 *1
    5-402 3,5-Cl2 CF3 2-CH3 E-5b 197.0-199.0
    5-403 3,5-Cl2 CF3 2-CH3 CH2CH2(T-33) *1
    5-404 3,5-Cl2 CF3 2-CH3 CH2CH2(T-39) *1
    5-405 3,5-Cl2 CF3 2-CH3 (E-9b)CH2CF3 *2
    5-406 3,5-Cl2 CF3 2-CH3 CH2(E-17a)H *1
    5-407 3,5-Cl2 CF3 2-CH3 CH[C(O)OCH3]2 *2
    5-408 3,5-Cl2 CF3 2-CH3 CH2C(O)NHOEt 141.0-145.0
    5-409 3,5-Cl2 CF3 2-CH3 CH2C(O)NHOCH2CH═CH2 *1
    5-410 3,5-Cl2 CF3 2-CH3 CH(CH3)C(O)NHEt *1
    5-411 3,5-Cl2 CF3 2-CH3 CH(CH3)C(O)NHPr-i 172.0-174.0
    5-412 3,5-Cl2 CF3 2-CH3 CH(CH3)C(O)NHCH2CF3 161.0-163.0
    5-413 3,5-Cl2 CF3 2-CH3 CH(CH3)C(O)NHCH2CH═CH2 175.0-178.0
    5-414 3,5-Cl2 CF3 2-CH3 T-48 *2
    5-415 3,5-Cl2 CF3 2-CH3 T-49 *2
    5-416 3,5-Cl2 CF3 2-CH3 CH[C(O)NHCH3]2 146.0-149.0
    5-417 3,5-Cl2 CF3 2-CH3 CH(OCH3)Ph *1
    5-418 3,5-Cl2 CF3 2-CH3 CH(CH3)(D-1a) 142.0-144.0
    5-419 3,5-Cl2 CF3 2-CH3 CH2(D-6a)CH3 155.0-157.0
    5-420 3,5-Cl2 CF3 2-CH3 CH(CF3)(D-6a)H *1
    5-421 3,5-Cl2 CF3 2-CH3 CH2(D-11a) *1
    5-422 3,5-Cl2 CF3 2-CH3 CH(CF3)(D-14a) 114.0-118.0
    5-423 3,5-Cl2 CF3 2-CH3 CH(CH3)(D-21a) *2
    5-424 3,5-Cl2 CF3 2-CH3 CH(CF3)(D-24a) *1
    5-425 3,5-Cl2 CF3 2-CH3 CH2(D-26a)CH3 *1
    5-426 3,5-Cl2 CF3 2-CH3 CH(CH3)(D-38a) *1
    5-427 3,5-Cl2 CF3 2-CH3 CH(CF3)(D-38a) *1
    5-428 3,5-Cl2 CF3 2-CH3 C(O)OCH2CF3 *1
    5-429 3,5-Cl2 CF3 2-CH3 C(O)NHCH2CF3  81.5-83.0
    5-430 3,5-Cl2 CF3 2-CH3 C(S)NHCH2CF3 137.5-140.0
    5-431 3,5-Cl2 CF3 2-CH3 C(D-49a)═C(CN)2 122.0-124.0
    5-432 3,5-Cl2 CF3 2-CH3 NHC(O)NHCH2CH2Cl 105.0-108.0
    5-433 3,5-Cl2 CF3 2-CH3 N(CH2C≡CH)Ph  76.0-84.0
    5-434 3,5-Cl2 CF3 2-CH3 Ph-4-CN *1
    5-435 3,5-Cl2 CF3 2-CH3 Ph-4-C(O)OH 248.0-251.0
    5-436 3,5-Cl2 CF3 2-CH3 Ph-4-C(O)OEt 230.0-232.0
    5-437 3,5-Cl2 CF3 2-CH3 Ph-4-C(O)NHCH2CH2Cl 188.0-195.0
    5-438 3,5-Cl2 CF3 2-CH3 Ph-4-C(O)NHCH2CF3 110.0-120.0
    5-439 3,5-Cl2 CF3 2-CH3 (D-8b)CH3 163.0-165.0
    5-440 3,5-Cl2 CF3 2-CH3 (D-15a)CH3  96.0-110.0
    5-441 3,5-Cl2 CF3 2-CH3 (D-17a)CH3  95.0-101.0
    5-442 3,5-Cl2 CF3 2-CH3 (D-17b)Cl 100.0-108.0
    5-443 3,5-Cl2 CF3 2-CH3 (D-21b)CH3 110.0-114.0
    5-444 3,5-Cl2 CF3 2-CH3 (D-21c)Cl 288.0-292.0
    5-445 3,5-Cl2 CF3 2-CH3 (D-21c)CH3 271.0-273.0
    5-446 3,5-Cl2 CF3 2-CH3 D-35a 117.0-126.0
    5-447 3,5-Cl2 CF3 2-CH3 (D-35b)CH3 227.0-230.0
    5-448 3,5-Cl2 CF3 2-CH3 (D-39c)SCH3 188.0-190.0
    5-449 3,5-Cl2 CF3 2-CH3 (D-42a)H 109.0-112.0
    5-450 3,5-Cl2 CH(OEt)2 2-CH3 CH2(D-47a) *1
    5-451 3,5-Br2 CF3 2-CH3 CH2C(O)OH 102.0-106.0
    5-452 3-CF3-5-NO2 CF3 2-CH3 CH2CF3 *1
    5-453 3-CF3-5-NO2 CF3 2-CH3 CH2(D-47a) *1
    5-454 3,5-Cl2-4-NH2 CF3 2-CH3 CH2CF3 153.0-154.0
    5-455 3,5-Cl2-4-NH2 CF3 2-CH3 CH2(D-47a) *1
    5-456 3,5-Cl2-4-NHC(O)OBu-t CF3 2-CH3 CH2CF3 *1
    5-457 3,5-Cl2-4-NHC(O)OBu-t CF3 2-CH3 CH2(D-47a) *1
    5-458 3,4-Cl2 CF3 2-CH3 CH2CF3 138.0-140.0
    5-459 3,4-Cl2 CF3 2-CH3 CH2C(O)NHCH2CF3 165.0-167.0
    5-460 3,4-Cl2 CF3 2-CH3 CH2(D-22a) *2
    5-461 3,4-Cl2 CF3 2-CH3 CH2(D-47a) *2
    5-462 3,5-Cl2 CF3 2-Cl H *1
    5-463 3,5-Cl2 CF3 2-Cl CH2C(O)NHCH2CF3 *1
    5-464 3,5-Cl2 CF3 2-Cl (D-50c)Cl 115.0-117.0
    5-465 3,5-Cl2 CF3 2-Br CH2C(O)NHCH2CF3 159.0-163.0
    5-466 3,5-Cl2 CF3 2-Br (D-57d)Cl 172.0-174.0
    5-467 3,5-Cl2 CF3 2-I H 126.0-128.0
    5-468 3,5-Cl2 CF3 2-I CH2C(O)NHCH2CF3 *1
    5-469 3,5-Cl2 CF3 2-I (D-47d)Cl 125.0-128.0
    5-470 3,5-Cl2 CF3 2-I (D-50c)Cl *1
    5-471 3,5-Cl2 CF3 2-CH3 CH3 *1
    5-472 3,5-Cl2 CF3 2-CH3 CH2CHF2 *1
    5-473 3,5-Cl2 CF3 2-CH3 CH2OCH3 *1
    5-474 3,5-Cl2 CF3 2-CH3 CH2OEt *1
    5-475 3,5-Cl2 CF3 2-CH3 CH2OPr-n *1
    5-476 3,5-Cl2 CF3 2-CH3 CH2OPr-i *1
    5-477 3,5-Cl2 CF3 2-CH3 CH2OCH2CH2Cl *1
    5-478 3,5-Cl2 CF3 2-CH3 CH2OCH2CHF2 *1
    5-479 3,5-Cl2 CF3 2-CH3 CH2OCH2CHCl2 *1
    5-480 3,5-Cl2 CF3 2-CH3 CH2OCH2CF3 111.0-114.0
    5-481 3,5-Cl2 CF3 2-CH3 CH2OCH2CCl3 *1
    5-482 3,5-Cl2 CF3 2-CH3 CH2OCH2CH2OCH3 *1
    5-483 3,5-Cl2 CF3 2-CH3 CH2OCH2CH═CH2 *1
    5-484 3,5-Cl2 CF3 2-CH3 CH2OCH2C≡CH *1
    5-485 3,5-Cl2 CF3 2-CH3 CH2OCH2Ph *1
    5-486 3,5-Cl2 CF3 2-CH3 CH2OC(O)CH3 *1
    5-487 3,5-Cl2 CF3 2-CH3 CH(CH3)OH *1
    5-488 3,5-Cl2 CF3 2-CH3 CH(CH3)OCH2CF3 *1
    5-489 3,5-Cl2 CF3 2-CH3 CH2CH2OCH2CF3 156.0-159.0
    5-490 3,5-Cl2 CF3 2-CH3 CH2CH2OCH2CH2OCH2CH2OCH3 *2
    5-491 3,5-Cl2 CF3 2-CH3 CH(CH3)CH2OH 160.0-164.0
    5-492 3,5-Cl2 CF3 2-CH3 CH(CH3)CH2OC(O)CH3 *1
    5-493 3,5-Cl2 CF3 2-CH3 CH(CH3)CH2OC(O)NHCH2CH2Cl *1
    5-494 3,5-Cl2 CF3 2-CH3 E-4a 144.0-147.0
    5-495 3,5-Cl2 CF3 2-CH3 E-5a(R) *1
    5-496 3,5-Cl2 CF3 2-CH3 E-23a *1
    5-497 3,5-Cl2 CF3 2-CH3 CH2SCH3 *1
    5-498 3,5-Cl2 CF3 2-CH3 CH2S(O)CH3 159.0-161.0
    5-499 3,5-Cl2 CF3 2-CH3 CH2SO2CH3 207.0-209.0
    5-500 3,5-Cl2 CF3 2-CH3 CH2SC(O)CH3 *1
    5-501 3,5-Cl2 CF3 2-CH3 CH2SC(S)OEt *1
    5-502 3,5-Cl2 CF3 2-CH3 CH2SO2OH•Q5 *1
    5-503 3,5-Cl2 CF3 2-CH3 CH2CH2SC(O)NHEt 148.0-150.0
    5-504 3,5-Cl2 CF3 2-CH3 CH2CH2SC(O)NH(Ph-4-F) *2
    5-505 3,5-Cl2 CF3 2-CH3 CH2CH2S(D-50a) *2
    5-506 3,5-Cl2 CF3 2-CH3 CH2CH2SO2(D-50a) *2
    5-507 3,5-Cl2 CF3 2-CH3 CH2NH2•Q1 155.0-157.0
    5-508 3,5-Cl2 CF3 2-CH3 CH2NHEt *1
    5-509 3,5-Cl2 CF3 2-CH3 CH2NHCH2CF3 *1
    5-510 3,5-Cl2 CF3 2-CH3 CH2N(CH2CF3)C(O)CH3 *1
    5-511 3,5-Cl2 CF3 2-CH3 CH2N(CH2CF3)C(O)OCH3 *1
    5-512 3,5-Cl2 CF3 2-CH3 CH2NHC(O)CH3 112.0-114.0
    5-513 3,5-Cl2 CF3 2-CH3 CH2NHC(O)CF3 191.0-194.0
    5-514 3,5-Cl2 CF3 2-CH3 CH2NHC(O)CH2CF3 212.0-217.0
    5-515 3,5-Cl2 CF3 2-CH3 CH2NHC(O)OCH3 *1
    5-516 3,5-Cl2 CF3 2-CH3 CH2NHC(O)OEt 110.0-120.0
    5-517 3,5-Cl2 CF3 2-CH3 CH2NHC(O)OCH2CF3 118.0-119.0
    5-518 3,5-Cl2 CF3 2-CH3 CH2NHC(O)NHEt 152.0-154.0
    5-519 3,5-Cl2 CF3 2-CH3 CH(CH3)NHC(O)OCH3  88.0-90.0
    5-520 3,5-Cl2 CF3 2-CH3 CH2CH2NHC(O)OCH2CH2Cl  96.0-99.0
    5-521 3,5-Cl2 CF3 2-CH3 CH2CH2NHSO2Et *1
    5-522 3,5-Cl2 CF3 2-CH3 CH2CH═NOCH2CF3 *1
    5-523 3,5-Cl2 CF3 2-CH3 CH(CH3)CH═NOCH3 *1
    5-524 3,5-Cl2 CF3 2-CH3 CH(CH2OH)C(O)OCH3 *1
    5-525 3,5-Cl2 CF3 2-CH3 CH2CH2CH2C(O)OEt *1
    5-526 3,5-Cl2 CF3 2-CH3 E-7e 192.0-194.5
    5-527 3,5-Cl2 CF3 2-CH3 CH2C(O)N(CH3)Et *1
    5-528 3,5-Cl2 CF3 2-CH3 CH2C(O)N(Et)2 *1
    5-529 3,5-Cl2 CF3 2-CH3 CH2C(O)NHPr-c 146.0-147.0
    5-530 3,5-Cl2 CF3 2-CH3 CH2C(O)NHBu-s 148.0-149.0
    5-531 3,5-Cl2 CF3 2-CH3 CH2C(O)NHCH2Pr-c 195.0-197.0
    5-532 3,5-Cl2 CF3 2-CH3 CH2C(O)NHCH2CH(OEt)2 *1
    5-533 3,5-Cl2 CF3 2-CH3 CH2C(O)NHCH2CN 198.0-201.0
    5-534 3,5-Cl2 CF3 2-CH3 CH2C(O)NHCH2C(O)NHCH3 170.0-172.0
    5-535 3,5-Cl2 CF3 2-CH3 CH2C(O)NHCH2C(O)NHCH2CF3 180.0-183.0
    5-536 3,5-Cl2 CF3 2-CH3 CH2C(O)NH(Ph-4-F) 235.0-237.0
    5-537 3,5-Cl2 CF3 2-CH3 CH2C(O)NH(Ph-4-CN) 267.0-269.0
    5-538 3,5-Cl2 CF3 2-CH3 CH(CH3)C(O)NH2 *1
    5-539 3,5-Cl2 CF3 2-CH3 CH(CH3)C(O)NHCH2CH2Cl(D) 162.0-164.0
    5-540 3,5-Cl2 CF3 2-CH3 CH(CH3)C(O)NHCH2CH2Cl(L) 149.0-151.0
    5-540(+) 99% d.e. [α]D 22.9 +54.77° (EtOH, c = 0.652) 103.0-105.0
    5-541 3,5-Cl2 CF3 2-CH3 CH(CH3)C(O)NHCH2CF3(D) 188.0-190.0
    [α]D 24.7 +14.89° (EtOH, c = 0.744)
    5-541(R) 95% d.e. [α]D 24.9 −54.42° (EtOH, c = 0.890) 164.0-166.0
    5-541(S) 95% d.e. [α]D 24.9 +50.27° (EtOH, c = 0.650) 216.0-217.0
    5-542 3,5-Cl2 CF3 2-CH3 CH(CH3)C(O)NHCH2CF3(L) 181.0-183.0
    5-543 3,5-Cl2 CF3 2-CH3 CH(Et)C(O)NHCH2CF3 197.0-205.0
    5-544 3,5-Cl2 CF3 2-CH3 CH(Pr-i)C(O)NHCH2CF3 220.0-224.0
    5-545 3,5-Cl2 CF3 2-CH3 CH2CH2CH2C(O)NHCH2CF3 172.0-175.0
    5-546 3,5-Cl2 CF3 2-CH3 T-50 *2
    5-547 3,5-Cl2 CF3 2-CH3 T-51 *2
    5-548 3,5-Cl2 CF3 2-CH3 CH2(D-14b)CF3 *1
    5-549 3,5-Cl2 CF3 2-CH3 CH2(D-17b)CF3 219.0-222.0
    5-550 3,5-Cl2 CF3 2-CH3 CH2(D-21e)  71.0-79.0
    5-551 3,5-Cl2 CF3 2-CH3 CH2(D-22a)•Q1 177.0-177.5
    5-552 3,5-Cl2 CF3 2-CH3 CH2(D-22a)•Q2  95.0-103.0
    5-553 3,5-Cl2 CF3 2-CH3 CH2(D-22a)•Q3 135.0-137.0
    5-554 3,5-Cl2 CF3 2-CH3 CH2(D-22a)•Q4 125.0-130.0
    5-555 3,5-Cl2 CF3 2-CH3 CH2(D-22b)SCH3 *1
    5-556 3,5-Cl2 CF3 2-CH3 CH2(D-22b)SO2CH3 *1
    5-557 3,5-Cl2 CF3 2-CH3 CH2(D-22b)CF3 *1
    5-558 3,5-Cl2 CF3 2-CH3 CH2(D-37a) *2
    5-559 3,5-Cl2 CF3 2-CH3 CH2(D-61b) *1
    5-560 3,5-Cl2 CF3 2-CH3 CH(CH3)(D-14a) *1
    5-561 3,5-Cl2 CF3 2-CH3 OCH3 *1
    5-562 3,5-Cl2 CF3 2-CH3 OCH2CH═CH2 158.0-160.0
    5-563 3,5-Cl2 CF3 2-CH3 SO2CH3 *1
    5-564 3,5-Cl2 CF3 2-CH3 SO2N(CH3)2 *2
    5-565 3,5-Cl2 CF3 2-CH3 N(Ph)C(O)CH2Cl *1
    5-566 3,5-Cl2 CF3 2-CH3 N═CHN(CH3)2 100.0-106.0
    5-567 3,5-Cl2 CF3 2-CH3 N═C(CH3)N(CH3)2  79.0-84.0
    5-568 3,5-Cl2 CF3 2-CH3 CHO 179.0-181.0
    5-569 3,5-Cl2 CF3 2-CH3 C(O)CH2CF3 148.0-150.0
    5-570 3,5-Cl2 CF3 2-CH3 C(O)OCH2CH2F 144.0-146.0
    5-571 3,5-Cl2 CF3 2-CH3 C(O)OCH2CHF2 165.0-168.0
    5-572 3,5-Cl2 CF3 2-CH3 C(O)OCH(CH2F)2 *1
    5-573 3,5-Cl2 CF3 2-CH3 C(O)OCH(CH2F)CH2Cl *1
    5-574 3,5-Cl2 CF3 2-CH3 C(O)NHCH3 161.0-163.0
    5-575 3,5-Cl2 CF3 2-CH3 C(O)N(CH3)2 *2
    5-576 3,5-Cl2 CF3 2-CH3 C(O)NHEt 178.0-180.0
    5-577 3,5-Cl2 CF3 2-CH3 C(O)NHCH2CH2Cl 210.0-213.0
    5-578 3,5-Cl2 CF3 2-CH3 C(O)NHCH2C(O)NHCH2CF3 231.0-232.0
    5-579 3,5-Cl2 CF3 2-CH3 C(O)NHCH2CH═CH2 160.0-162.0
    5-580 3,5-Cl2 CF3 2-CH3 C(O)NHCH2(Ph-4-F) 101.0-104.0
    5-581 3,5-Cl2 CF3 2-CH3 C(O)NHCH2(D-47a) *1
    5-582 3,5-Cl2 CF3 2-CH3 C(O)NH(Ph-4-F) 188.0-191.0
    5-583 3,5-Cl2 CF3 2-CH3 C(O)(T-33) *2
    5-584 3,5-Cl2 CF3 2-CH3 C(S)NHCH3  98.0-101.0
    5-585 3,5-Cl2 CF3 2-CH3 Ph *1
    5-586 3,5-Cl2 CF3 2-CH3 Ph-2-F 164.0-167.0
    5-587 3,5-Cl2 CF3 2-CH3 Ph-3-F 163.0-171.0
    5-588 3,5-Cl2 CF3 2-CH3 Ph-4-F *1
    5-589 3,5-Cl2 CF3 2-CH3 Ph-4-Cl 165.0-169.0
    5-590 3,5-Cl2 CF3 2-CH3 Ph-4-CF3  95.0-99.0
    5-591 3,5-Cl2 CF3 2-CH3 Ph-2-OH *1
    5-592 3,5-Cl2 CF3 2-CH3 Ph-4-OCH3 180.0-182.0
    5-593 3,5-Cl2 CF3 2-CH3 Ph-4-OCF3 165.0-167.0
    5-594 3,5-Cl2 CF3 2-CH3 Ph-4-OSO2CH3 160.0-163.0
    5-595 3,5-Cl2 CF3 2-CH3 Ph-4-SCH3 181.0-183.0
    5-596 3,5-Cl2 CF3 2-CH3 Ph-4-S(O)CH3 119.0-126.0
    5-597 3,5-Cl2 CF3 2-CH3 Ph-4-SO2CH3 222.0-225.0
    5-598 3,5-Cl2 CF3 2-CH3 Ph-4-SO2NH2 126.0-130.0
    5-599 3,5-Cl2 CF3 2-CH3 Ph-4-NO2 141.0-148.0
    5-600 3,5-Cl2 CF3 2-CH3 Ph-2-CN 168.0-175.0
    5-601 3,5-Cl2 CF3 2-CH3 Ph-3-CN *1
    5-602 3,5-Cl2 CF3 2-CH3 Ph-4-C(O)NH2 209.0-213.0
    5-603 3,5-Cl2 CF3 2-CH3 Ph-2-C(O)NHPr-i *1
    5-604 3,5-Cl2 CF3 2-CH3 Ph-2,4-F2 *1
    5-605 3,5-Cl2 CF3 2-CH3 Ph-2,5-F2 *1
    5-606 3,5-Cl2 CF3 2-CH3 Ph-2,6-F2 177.5-181.0
    5-607 3,5-Cl2 CF3 2-CH3 Ph-3,4-F2 154.0-160.0
    5-608 3,5-Cl2 CF3 2-CH3 Ph-2-F-4-Cl 140.0-142.0
    5-609 3,5-Cl2 CF3 2-CH3 Ph-3,4-Cl2 *1
    5-610 3,5-Cl2 CF3 2-CH3 Ph-3,5-Cl2 *1
    5-611 3,5-Cl2 CF3 2-CH3 Ph-3-NO2-4-F *1
    5-612 3,5-Cl2 CF3 2-CH3 Ph-2,4,6-F3 *1
    5-613 3,5-Cl2 CF3 2-CH3 Ph-2,6-F2-4-Br 215.0-217.0
    5-614 3,5-Cl2 CF3 2-CH3 D-3a 102.0-107.0
    5-615 3,5-Cl2 CF3 2-CH3 D-5a *1
    5-616 3,5-Cl2 CF3 2-CH3 (D-10b)CH3 190.0-193.0
    5-617 3,5-Cl2 CF3 2-CH3 D-14a *1
    5-618 3,5-Cl2 CF3 2-CH3 (D-14c)Br *1
    5-619 3,5-Cl2 CF3 2-CH3 (D-21b)CF3 *1
    5-620 3,5-Cl2 CF3 2-CH3 D-21e 182.0-187.0
    5-621 3,5-Cl2 CF3 2-CH3 D-61b *1
    5-622 3,5-Cl2 CF3 2-CH3 D-41a 223.0-224.0
    5-623 3,5-Cl2 CF3 2-CH3 (D-47d)Cl 129.0-132.5
    5-624 3,5-Cl2 CF3 2-CH3 (D-47d)Br 181.0-183.0
    5-625 3,5-Cl2 CF3 2-CH3 (D-47d)I 180.0-186.0
    5-626 3,5-Cl2 CF3 2-CH3 (D-47d)CH3 110.0-113.0
    5-627 3,5-Cl2 CF3 2-CH3 (D-47d)CF3 184.0-186.0
    5-628 3,5-Cl2 CF3 2-CH3 (D-47d)NO2 113.0-116.0
    5-629 3,5-Cl2 CF3 2-CH3 (D-47d)CN *1
    5-630 3,5-Cl2 CF3 2-CH3 (D-47e)Cl *1
    5-631 3,5-Cl2 CF3 2-CH3 (D-47e)Br *1
    5-632 3,5-Cl2 CF3 2-CH3 (D-47f)-3,5-Cl2 120.0-124.0
    5-633 3,5-Cl2 CF3 2-CH3 (D-48e)Cl *1
    5-634 3,5-Cl2 CF3 2-CH3 (D-48e)CN *1
    5-635 3,5-Cl2 CF3 2-CH3 (D-49b)Cl *1
    5-636 3,5-Cl2 CF3 2-CH3 D-49e 173.0-177.0
    5-637 3,5-Cl2 CF3 2-CH3 (D-50b)CH3 *1
    5-638 3,5-Cl2 CF3 2-CH3 (D-50c)Cl 137.0-141.0
    5-639 3,5-Cl2 CF3 2-CH3 (D-50c)Br 178.0-181.0
    5-640 3,5-Cl2 CF3 2-CH3 (D-50c)I *1
    5-641 3,5-Cl2 CF3 2-CH3 (D-51c)Cl  85.0-87.0
    5-642 3,5-Cl2 CF3 2-CH3 D-52a 207.0-211.0
    5-643 3,5-Cl2 CF3 2-CH3 D-53a 139.0-144.0
    5-644 3,5-Cl2 CF3 2-CH3 (D-53b)Br 251.0-253.0
    5-645 3,5-Cl2 CF3 2-CH3 (D-54b)Cl  99.0-102.5
    5-646 3,5-Cl2 CF2Cl 2-CH3 CH2C(O)NHCH2CF3 171.0-173.0
    5-647 3,5-Cl2-4-CH3 CF3 2-CH3 CH2CF3 *2
    5-648 3,5-Cl2-4-CH3 CF3 2-CH3 CH2(D-47a) *2
    5-649 3,5-Cl2-4-OH CF3 2-CH3 CH2(D-47a) *2
    5-650 3,5-Cl2-4-OCH3 CF3 2-CH3 CH2CF3 198.0-199.0
    5-651 3,5-Cl2-4-OCH3 CF3 2-CH3 CH2(D-47a) *2
    5-652 3,5-Cl2-4-OC(O)OBu-t CF3 2-CH3 CH2(D-47a) *2
    5-653 3,5-Cl2-4-N(CH3)2 CF3 2-CH3 CH2CF3 *2
    5-654 3,5-Cl2-4-N(CH3)2 CF3 2-CH3 CH2(D-47a) *2
    5-655 3,5-Cl2 CF3 2-I CH2OCH2CF3 *1
    5-656 3,5-Cl2 CF3 2-I E-4a *1
    5-657 3,5-Cl2 CF3 3-I CH2C(O)NHCH2CF3 *1
    5-658 3,5-Cl2 CF3 2-CH3 (E-23b)OCH3 *1
    5-659 3,5-Cl2 CF3 2-CH3 CH2C(O)NH(E-4a)  86.0-91.0
    5-660 3,5-Cl2 CF3 2-CH3 CH═CH2 *1
    5-661 3,5-Cl2 CF3 2-CH3 CH2C≡CBr 166.0-169.0
    5-662 3,5-Cl2 CF3 2-CH3 N(CH3)C(O)NHCH2CF3 *1
    5-663 3,5-Cl2 CF3 2-CH3 OC(O)NHCH2CF3 111.0-114.0
    5-664 3,5-Cl2 CF3 2-CH3 C(O)CH3 151.0-154.5
    5-665 3,5-Cl2 CF3 2-CH3 C(O)Et 169.0-172.0
    5-666 3,5-Cl2 CF3 2-CH3 D-22a 228.0-230.0
    5-667 3,5-Cl2 CF3 2-CH3 (D-22b)Br *1
    5-668 3,5-Cl2 CF3 2-CH3 (D-47b)Cl *1
    5-669 3,5-Cl2 CF2Cl 2-Cl H *1
    5-670 3-Cl-5-Br CF3 2-CH3 H *1
    5-671 3,5-Br2 CF3 2-Cl H 105.0-108.0
    5-672 3,5-(CF3)2 CF3 2-CH3 H *1
    5-673 3,5-Cl2 CF3 2-CH3 D-2a 105.0-110.0
    5-674 3,5-Cl2 CF3 2-CH3 (D-50c)CN 118.0-121.0
    5-675 3,5-Cl2 CF3 2-CH3 (D-52b)Cl 231.0-234.0
    5-676 3,5-Cl2 CF3 2-CH3 (D-53b)Cl 242.0-243.0
    5-677 3,5-Cl2 CF3 2-Et H *1
    5-678 3,5-Cl2 CF3 2-CH2OCH3 H 186.0-188.0
    5-679 3,5-Cl2 CF3 2-OCHF2 H *1
    5-680 3,5-Cl2 CF3 2-NO2 H *1
    5-681 3,5-Cl2 CF3 2-NH2 H 190.0-193.0
    5-682 3,5-Cl2 CF3 2-NHC(O)CH3 H *1
    5-683 3,4,5-Cl3 CF3 2-CH3 H 153.0-155.0
    5-684 3-Cl-5-CF3 CF3 2-CH3 CH2CF3 *1
    5-685 3,5-Cl2-4-F CF3 2-CH3 CH2CF3 *1
    5-686 3-Cl-4-F-5-CF3 CF3 2-CH3 CH2CF3 *1

    In Table above, the indications of “5-529 (R)*” and “5-529 (S)*” show optical isomers in which the absolute configuration of 5-position of 4,5-dihydroisooxazole ring is R- and S-configuration, respectively.
  • TABLE 12
    Figure US20150105398A1-20150416-C00082
    No. (X)m R3 (Y)n R2 R1 m.p. (° C.)
    6-001 3,5-Cl2 CF3 2-Cl Et Et *1
    6-002 3,5-Cl2 CF3 2-CH3 NH2 CH3 138.0-139.0
    6-003 3,5-Cl2 CF3 2-CH3 Et Et *1
    6-004 3,5-Cl2 CF3 2-CH3 NH2 Et 76.0-78.0
    6-005 3,5-Cl2 CF3 2-CH3 NHC(O)CH3 Et *1
    6-006 3,5-Cl2 CF3 2-CH3 N═C(CH3)2 Et *1
    6-007 3,5-Cl2 CF3 2-CH3 CH2CN n-Bu *1
    6-008 3,5-Cl2 CF3 2-CH3 CH2CN CH2CN *1
    6-009 3,5-Cl2 CF3 2-CH3 OH CH2Ph 175.0-177.0
    6-010 3,5-Cl2 CF3 2-CH3 OCH3 CH2Ph *1
    6-011 3,5-Cl2 CF3 2-CH3 OC(O)CH3 CH2Ph *1
    6-012 3,5-Cl2 CF3 2-CH3 OC(O)OCH3 CH2Ph *1
    6-013 3,5-Cl2 CF3 2-CH3 OSO2CH3 CH2Ph *1
    6-014 3,5-Cl2 CF3 2-CH3 NH2 CH2Ph 135.0-136.0
    6-015 3,5-Cl2 CF3 2-CH3 CH2CN CH2(D-22a) *1
    6-016 3,5-Cl2 CF3 2-CH3 CH2C≡CH CH2(D-22a) *1
    6-017 3,5-Cl2 CF3 2-CH3 C(O)CH3 CH2(D-22a) *1
    6-018 3,5-Cl2 CF3 2-CH3 C(O)Et CH2(D-22a) *1
    6-019 3,5-Cl2 CF3 2-CH3 C(O)OCH3 CH2(D-22a) *1
    6-020 3,5-Cl2 CF3 2-CH3 CH3 CH2(D-47a) *1
    6-021 3,5-Cl2 CF3 2-CH3 Et CH2(D-47a) *1
    6-022 3,5-Cl2 CF3 2-CH3 n-Pr CH2(D-47a) *1
    6-023 3,5-Cl2 CF3 2-CH3 i-Pr CH2(D-47a) *1
    6-024 3,5-Cl2 CF3 2-CH3 c-Pr CH2(D-47a) *1
    6-025 3,5-Cl2 CF3 2-CH3 t-Bu CH2(D-47a) *1
    6-026 3,5-Cl2 CF3 2-CH3 CH2CF3 CH2(D-47a) *1
    6-027 3,5-Cl2 CF3 2-CH3 CH2OCH3 CH2(D-47a) *1
    6-028 3,5-Cl2 CF3 2-CH3 CH2CH2OCH3 CH2(D-47a) *1
    6-029 3,5-Cl2 CF3 2-CH3 CH2SCH3 CH2(D-47a) *1
    6-030 3,5-Cl2 CF3 2-CH3 CH2C(O)OCH3 CH2(D-47a) *1
    6-031 3,5-Cl2 CF3 2-CH3 CH2CN CH2(D-47a) *1
    6-032 3,5-Cl2 CF3 2-CH3 CH2CH═CH2 CH2(D-47a) *1
    6-033 3,5-Cl2 CF3 2-CH3 CH2C≡CH CH2(D-47a) *1
    6-034 3,5-Cl2 CF3 2-CH3 C(O)CH3 CH2(D-47a) *1
    6-035 3,5-Cl2 CF3 2-CH3 C(O)Et CH2(D-47a) *1
    6-036 3,5-Cl2 CF3 2-CH3 C(O)Pr-n CH2(D-47a) *1
    6-037 3,5-Cl2 CF3 2-CH3 C(O)Pr-i CH2(D-47a) *1
    6-038 3,5-Cl2 CF3 2-CH3 C(O)Pr-c CH2(D-47a) *1
    6-039 3,5-Cl2 CF3 2-CH3 C(O)Bu-t CH2(D-47a) *1
    6-040 3,5-Cl2 CF3 2-CH3 C(O)CH2OCH3 CH2(D-47a) 53.0-55.0
    6-041 3,5-Cl2 CF3 2-CH3 C(O)CH═CH2 CH2(D-47a) *1
    6-042 3,5-Cl2 CF3 2-CH3 C(O)Ph CH2(D-47a) *1
    6-043 3,5-Cl2 CF3 2-CH3 C(O)OCH3 CH2(D-47a) *1
    6-044 3,5-Cl2 CF3 2-CH3 C(O)OEt CH2(D-47a) *1
    6-045 3,5-Cl2 CF3 2-CH3 C(O)OPr-i CH2(D-47a) *1
    6-046 3,5-Cl2 CF3 2-CH3 C(O)OBu-i CH2(D-47a) *1
    6-047 3,5-Cl2 CF3 2-CH3 C(O)OCH2CH2Cl CH2(D-47a) *1
    6-048 3,5-Cl2 CF3 2-CH3 C(O)OCH2CH2OCH3 CH2(D-47a) *1
    6-049 3,5-Cl2 CF3 2-CH3 C(O)OCH2CH═CH2 CH2(D-47a) *1
    6-050 3,5-Cl2 CF3 2-CH3 C(O)SCH3 CH2(D-47a) *1
    6-051 3,5-Cl2 CF3 2-CH3 SO2CH3 CH2(D-47a) *1
    6-052 3,5-Cl2 CF3 2-CH3 NH2 CH2(D-47a) 126.0-130.0
    6-053 3,5-Cl2 CF3 2-CH3 N(CH3)2 CH2(D-47a) *1
    6-054 3,5-Cl2 CF3 2-CH3 Et CH2(D-48e)Cl *1
    6-055 3,5-Cl2 CF3 2-CH3 c-Pr CH2(D-49a) *1
    6-056 3,5-Cl2 CF3 2-CH3 C(O)Et CH2(D-50a) *1
    6-057 3,5-Cl2 CF3 2-CH3 —CH2CH2SCH2CH2— 209.5-211.5
    6-058 3,5-Cl2 CF3 2-CH3 CH3 N(CH3)Ph 153.0-154.0
    6-059 3,5-Cl2 CF3 2-CH3 Et N(CH3)Ph 78.0-79.0
    6-060 3,5-Cl2 CF3 2-CH3 CH2OCH3 N(CH3)Ph 72.0-73.0
    6-061 3,5-Cl2 CF3 2-CH3 CH2CH═CH2 N(CH3)Ph 76.0-77.0
    6-062 3,5-Cl2 CF3 2-CH3 CH2C≡CH N(CH3)Ph 83.0-84.0
    6-063 3,5-Cl2 CF3 2-CH3 CH2CN N(CH3)Ph 69.0-70.0
    6-064 3,5-Cl2 CF3 2-CH3 C(O)CH3 N(CH3)Ph 82.0-83.0
    6-065 3,5-Cl2 CF3 2-CH3 C(O)OCH3 N(CH3)Ph 70.0-71.0
    6-066 3,5-Cl2 CF3 2-CH3 CH3 NH(D-50a) 107.0-109.0
    6-067 3,5-Cl2 CF3 2-CH3 Et NH(D-50a) 185.0-187.0
    6-068 3,5-Cl2 CF3 2-CH2— H 234.0-236.0
    6-069 3,5-Cl2 CF3 2-CH2— CH3 *1
    6-070 3,5-Cl2 CF3 2-CH2— CH2(D-47a) *1
    6-071 3,5-Cl2 CF3 2-N(CH3)CH2— CH2(D-47a) *1
    6-072 3,5-Cl2 CF3 2-N═CH— H 249.0-251.0
    6-073 3,5-Cl2 CF3 2-N═CH— CH2(D-47a) *1
    6-074 3,5-Cl2 CF2Cl 2-CH3 C(O)CH3 CH2CF3 *1
    6-075 3,5-Br2 CF3 2-CH3 C(O)CH3 CH2CF3 *1
    6-076 3,5-Br2 CF3 2-CH3 C(O)CH3 CH2(D-47a) *1
    6-077 3,5-Cl2 CF3 2-CH3 C(O)OCH3 CH2CF3 *2
    6-078 3,5-Cl2 CF3 2-CH3 CH2OCH3 CH2(D-22a) *1
    6-079 3,5-Cl2 CF3 2-CH3 CH2OEt CH2(D-47a) *1
    6-080 3,5-Cl2 CF3 2-CH3 C(O)OCH3 CH(CH3)(D-47a) *2
    6-080(+)* 98% e.e. [α]D 22.4 + 35.40O (CHCl3, c = 0.397) *2
    6-080(−)* 99% e.e. [α]D 22.2 − 37.20O (CHCl3, c = 0.473) *2
    6-081 3,5-Cl2 CF3 2-CH3 C(O)CH3 N(CH3)(D-47a) *1
    6-082 3,5-Cl2 CF3 2-CH3 C(O)OCH3 N(CH3)(D-47a) *1
    6-083 3,5-Cl2 CF3 2-CH3 C(O)CH3 N(CH3)(D-50a) *2
    6-084 3,5-Cl2 CF3 2-CH3 C(O)OCH3 N(CH3)(D-50a) *1
    6-085 3,5-Cl2 CF3 2-CH3 —C(O)CH2CH2CH2— *1
    6-086 3,5-Cl2 CF3 2-CH3 —C(O)CH2CH2C(O)— *1
    6-087 3,5-Cl2 CF3 2-CH3 —CH2CH2N(Ph)CH2CH2— 84.0-88.0
    6-088 3,5-Cl2 CF3 2-CH3 —CH2CH2N(D-47a)CH2CH2— 87.0-92.0
    6-089 3,5-Cl2 CF3 2-CH3 C(O)Et CH3 *1
    6-090 3,5-Cl2 CF3 2-CH3 C(O)CF3 CH3 181.0-183.0
    6-091 3,5-Cl2 CF3 2-CH3 C(O)OCH2CH2CF3 CH3 148.0-150.0
    6-092 3,5-Cl2 CF3 2-CH3 CH2OEt CH2OEt *1
    6-093 3,5-Cl2 CF3 2-CH3 C(O)CH3 CH2OEt *1
    6-094 3,5-Cl2 CF3 2-CH3 CH3 CH2OCH2CF3 *1
    6-095 3,5-Cl2 CF3 2-CH3 C(O)CH3 CH2OCH2CF3 *1
    6-096 3,5-Cl2 CF3 2-CH3 C(O)OCH3 CH2CH2OCH3 *1
    6-097 3,5-Cl2 CF3 2-CH3 CH3 CH2(E-10a) *1
    6-098 3,5-Cl2 CF3 2-CH3 C(O)CH3 CH2(E-10a) *1
    6-099 3,5-Cl2 CF3 2-CH3 C(O)OCH3 CH2(E-10a) *1
    6-100 3,5-Cl2 CF3 2-CH3 C(O)CH3 E-4a *1
    6-101 3,5-Cl2 CF3 2-CH3 CH3 CH2CH═NOCH3 *1
    6-102 3,5-Cl2 CF3 2-CH3 C(O)CH3 CH2CH═NOCH3 *1
    6-103 3,5-Cl2 CF3 2-CH3 C(O)OCH3 CH2CH═NOCH3 *1
    6-104 3,5-Cl2 CF3 2-CH3 C(O)OCH3 CH2C(O)NHCH2CF3 115.0-120.0
    6-105 3,5-Cl2 CF3 2-CH3 C(O)OCH3 CH2(Ph-4-OCH3) *1
    6-106 3,5-Cl2 CF3 2-CH3 C(O)OCH3 CH2(Ph-4-NO2) *1
    6-107 3,5-Cl2 CF3 2-CH3 C(O)OCH3 CH2(Ph-4-Ph) *1
    6-108 3,5-Cl2 CF3 2-CH3 C(O)OBu-t CH2(D-14b)CF3 *1
    6-109 3,5-Cl2 CF3 2-CH3 C(O)OCH3 CH2(D-61b) *1
    6-110 3,5-Cl2 CF3 2-CH3 C(O)OCH3 CH2(D-47a) · Q1 70.0-100.0
    6-111 3,5-Cl2 CF3 2-CH3 Ph-4-F CH2(D-47a) *1
    6-112 3,5-Cl2 CF3 2-CH3 C(O)OCH3 CH2(D-50a) *1
    6-113 3,5-Cl2 CF3 2-CH3 —CH2CH2CH2CH[C(O)NHCH2CF3]— *1
    6-114 3,5-Cl2 CF3 2-CH3 —CH2OCH2CH2— *1
    6-115 3,5-Cl2 CF3 2-CH3 —CH2SCH2CH2— *1
    6-116 3,5-Cl2 CF3 2-CH3 —CH2SO2CH2CH2— 206.0-208.0
    6-117 3,5-Cl2 CF3 2-CH3 —CH2CH2OCH2CH2— 217.0-219.0
    6-118 3,5-Cl2 CF3 2-CH3 —CH2CH2SO2CH2CH2— 223.0-226.0
    6-119 3,5-Cl2 CF3 2-CH3 —CH2CH2N(CH3)CH2CH2— *1
    6-120 3,5-Cl2 CF3 2-CH3 C(O)OCH3 OCH3 *1
    6-121 3,5-Cl2 CF3 2-CH3 C(O)OCH3 N(CH3)2 *1
    6-122 3,5-Cl2 CF3 2-CH3 C(O)CH3 C(O)CH3 *1
    6-123 3,5-Cl2 CF3 2-CH3 —CH2CH(CH2F)OC(O)— *1
    6-124 3,5-Cl2 CF3 2-CH3 C(O)OCH3 C(O)N(CH3)2 *1
    6-125 3,5-Cl2 CF3 2-CH3 CH3 C(O)NHEt *1
    6-126 3,5-Cl2 CF3 2-CH3 CH3 C(O)NHCH2CF3 *1
    6-127 3,5-Cl2 CF3 2-CH3 —CH2CH2N(CH2CF3)C(O)— 167.0-170.0
    6-128 3,5-Cl2 CF3 2-C(═CH2)— CH2CF3 141.0-144.0
    6-129 3,5-Cl2 CF3 2-CH3 CH3 E-4a 155.0-157.0
    6-130 3,5-Cl2 CF3 2-CH3 CH2OCH3 E-4a *1
    6-131 3,5-Cl2 CF3 2-CH3 C(O)Et E-4a *1
    6-132 3,5-Cl2 CF3 2-CH3 C(O)Pr-i E-4a *1
    6-133 3,5-Cl2 CF3 2-CH3 CH3 E-6a 146.0-151.0
    6-134 3,5-Cl2 CF3 2-CH3 CH3 CH3 166.5-168.5

    In Table above, the indications of “6-080 (+)*” and “6-080 (−)*” show optically active forms of 1-(2-pyridyl)ethylamine moiety.
  • TABLE 13
    Figure US20150105398A1-20150416-C00083
    No. (X)m R3 (Y)n R2 R1 m.p. (° C.)
    7-001 3,5-Cl2 CF3 — H H 227.0-232.0
    7-002 3,5-Cl2 CF3 — H CH2CF3 *1
    7-003 3,5-Cl2 CF3 — H CH2(D-22a) *1
    7-004 3,5-Cl2 CF3 — H CH2(D-47a) 165.0-167.0
    7-005 3,5-Cl2 CF3 2-F H CH2(D-22a) 171.0-173.0
    7-006 3,5-Cl2 CF3 2-Cl H CH2(D-22a) 90.0-92.0
    7-007 3,5-Cl2 CF3 2-CH3 H CH2CF3 *1
    7-008 3,5-Cl2 CF3 2-CH3 H CH2(D-22a) *1
    7-009 3,5-Cl2 CF3 2-CH3 H CH2(D-47a) *1
    7-010 3,5-Cl2 CF3 2-CH3 H N(CH3)Ph 100.0-111.0
  • TABLE 14
    Figure US20150105398A1-20150416-C00084
    m.p.
    No. (X)m R3 (Y)n R1a R2a (° C.)
    8-001 3,5-Cl2 CF3 — —N(CH3)CH═CHS— *1
    8-002 3,5-Cl2 CF3 2-CH3 —N(CH3)CH═CHS— *1
    8-003 3,5-Cl2 CF3 2-CH3 —N(Pr-n)CH═CHS— *1
    8-004 3,5-Cl2 CF3 2-CH3 —N(CH3)N═CHCH2S— *1
    8-005 3,5-Cl2 CF3 2-CH3 O —N(CH3)CH═CHCH═N— *1
    8-006 3,5-Cl2 CF3 2-CH3 O —N(CH3)N═CHS— *1
    8-007 3,5-Cl2 CF3 2-CH3 O —N(CH3)N═CClCH═CH— *2
  • TABLE 15
    Figure US20150105398A1-20150416-C00085
    Substituent G in the above-mentioned formula is the structure of G-3, G-6, G-18 or
    G-20 mentioned below.
    Figure US20150105398A1-20150416-C00086
    No. G (X)m R3 (Y)n R2 R1 m.p. (° C.)
    9-001 G-3  6-F CF3 — H CH2CF3 175.0-177.0
    9-002 G-3  6-Cl CF3 — H CH2CF3 192.0-195.0
    9-003 G-3  5-Br CF3 2-CH3 H CH2CF3 *1
    9-004 G-3  6-OCH3 CF3 — H CH2CF3 150.0-152.0
    9-005 G-6  4,6-Cl2 CF3 — H CH2CF3 140.0-142.0
    9-006 G-6  4,6-Cl2 CF3 2-CH3 H CH2CF3 131.0-134.0
    9-007 G-18 — CF3 — H CH2CF3 156.0-157.0
    9-008 G-20 4-CF3 CF3 2-CH3 H CH2CF3 *1
    9-009 G-20 4-CF3 CF3 2-CH3 H CH2(D-47a) *1
    9-010 G-13 5-Cl CF3 2-CH3 H CH2CF3 *1
    9-011 G-13 5-Cl CF3 2-CH3 H CH2(D-47a) *1
  • TABLE 16
    Figure US20150105398A1-20150416-C00087
    No. (X)m A1 A2 A3 (Y)n R1 m.p. (° C.)
    10-001 3,5-Cl2 N C C — CH2CF3 *1
    10-002 3,5-Cl2 N C C — CH2(D-47a) *1
    10-003 3,5-Cl2 N(O) C C — CH2CF3 *1
    10-004 3,5-Cl2 C N C — CH2CF3 *1
    10-005 3,5-Cl2 C N C — CH2(D-47a) *1
  • TABLE 17
    Figure US20150105398A1-20150416-C00088
    No. (X)m R3 (Y)n R m.p. (° C.)
    11-001 3-Cl CF3 — C(O)OH 220.0-225.0
    11-002 3-Cl CF3 — C(O)OCH3 100.0-101.0
    11-003 4-Cl CF3 — C(O)OH 255.0-257.0
    11-004 4-Cl CF3 — C(O)OCH3 *1
    11-005 3-I CF3 2-CH3 C(O)OH 169.0-172.0
    11-006 3-I CF3 2-CH3 C(O)OCH3 *1
    11-007 3-NO2 CF3 2-CH3 C(O)OCH3 *1
    11-008 3,4-F2 CF3 — C(O)OH 246.0-248.0
    11-009 3,4-F2 CF3 — C(O)OCH3 132.0-133.0
    11-010 2,4-Cl2 CF3 — C(O)OH 104.0-106.0
    11-011 2,4-Cl2 CF3 — C(O)OCH3 103.0-106.0
    11-012 2,5-Cl2 CF3 — C(O)OH 97.0-100.0
    11-013 2,5-Cl2 CF3 — C(O)OCH3 163.0-165.0
    11-014 3,4-Cl2 H — C(O)OCH3 115.0-117.0
    11-015 3,4-Cl2 CH3 — C(O)OCH3 98.0-100.0
    11-016 3,4-Cl2 CF3 — C(O)OH 215.0-217.0
    11-017 3,4-Cl2 CF3 — C(O)OCH3 95.0-97.0
    11-018 3,4-Cl2 CF3 — C(O)OBu-t 94.0-95.0
    11-019 3,4-Cl2 CF3 — C(O)OCH2Ph 94.0-95.0
    11-020 3,4-Cl2 Ph — C(O)OCH3 143.0-145.0
    11-021 3,5-Cl2 CF3 — CH2OH 108.0-110.0
    11-022 3,5-Cl2 CF3 — OH 153.0-155.5
    11-023 3,5-Cl2 CF3 — OCH3 93.0-96.5
    11-024 3,5-Cl2 CF3 — NO2 161.0-162.0
    11-025 3,5-Cl2 CF3 — NH2 98.0-99.0
    11-026 3,5-Cl2 CF3 — CN 140.0-142.0
    11-027 3,5-Cl2 CF3 — C(O)OH 237.0-240.0
    11-028 3,5-Cl2 CF3 — C(O)OCH3 94.0-96.0
    11-029 3,5-Cl2 CF3 2-F CH2Br *2
    11-030 3,5-Cl2 CF3 2-F CH2OC(O)CH3 *2
    11-031 3,5-Cl2 CF3 2-F CH2OH *1
    11-032 3,5-Cl2 CF3 2-F C(O)OH 172.0-174.0
    11-033 3,5-Cl2 CF3 3-F Br 136.0-138.0
    11-034 3,5-Cl2 CF3 3-F C(O)OH *1
    11-035 3,5-Cl2 CF3 3-F C(O)OEt 94.0-96.0
    11-036 3,5-Cl2 CF3 2-Cl OSO2CF3 154.0-157.5
    11-037 3,5-Cl2 CF3 2-Cl C(O)OH 150.0-151.0
    11-038 3,5-Cl2 CF3 2-Cl C(O)OCH3 *2
    11-039 3,5-Cl2 CF3 3-Cl Br *2
    11-040 3,5-Cl2 CF3 3-Cl C(O)OH 187.0-188.0
    11-041 3,5-Cl2 CF3 3-Cl C(O)OEt *1
    11-042 3,5-Cl2 CF3 2-Br C(O)OCH3 83.0-86.0
    11-043 3,5-Cl2 CF3 2-I CH3 130.0-132.0
    11-044 3,5-Cl2 CF3 2-I CH2Br *1
    11-045 3,5-Cl2 CF3 2-I CH2OC(O)CH3 *1
    11-046 3,5-Cl2 CF3 2-I CH2OH *1
    11-047 3,5-Cl2 CF3 2-I C(O)OH *1
    11-048 3,5-Cl2 CF3 2-I C(O)OCH3 *2
    11-049 3,5-Cl2 CF3 2-CH3 NO2 135.0-136.0
    11-050 3,5-Cl2 CF3 2-CH3 NH2 *1
    11-051 3,5-Cl2 CF3 2-CH3 F 67.0-68.0
    11-052 3,5-Cl2 CF3 2-CH3 Br 113.0-114.5
    11-053 3,5-Cl2 CF3 2-CH3 C(O)OH 150.0-152.0
    11-054 3,5-Cl2 CF3 2-CH3 C(O)OCH3 96.0-99.5
    11-055 3,5-Cl2 CF3 2-CH3 C(O)OEt nD 21. 4°C.1.5474
    11-056 3,5-Cl2 CF3 2-CH3 C(O)OCH2(D-47a) *2
    11-057 3,5-Cl2 CF3 2-CH3 C(O)(D-14a) *1
    11-058 3,5-Cl2 CF3 2-CH3 C(O)(D-38a) 58.0-59.0
    11-059 3,5-Cl2 CF3 2-Et C(O)OCH3 *2
    11-060 3,5-Cl2 CF3 2-CH2Br C(O)OCH3 *2
    11-061 3,5-Cl2 CF3 2-CF3 F *1
    11-062 3,5-Cl2 CF3 2-CF3 CN *1
    11-063 3,5-Cl2 CF3 2-CF3 C(O)OCH3 *2
    11-064 3,5-Cl2 CF3 2-OH NO2 110.0-113.0
    11-065 3,5-Cl2 CF3 2-OH NH2 178.0-181.0
    11-066 3,5-Cl2 CF3 2-OCH3 OSO2CF3 *1
    11-067 3,5-Cl2 CF3 2-OCH3 C(O)OH *1
    11-068 3,5-Cl2 CF3 2-OCH3 C(O)OEt 142.0-144.0
    11-069 3,5-Cl2 CF3 2-OCF3 NH2 81.5-84.0
    11-070 3,5-Cl2 CF3 2-OCF3 I *1
    11-071 3,5-Cl2 CF3 2-OCF3 C(O)OCH3 *1
    11-072 3,5-Cl2 CF3 2-SCH3 C(O)OH 151.0-152.0
    11-073 3,5-Cl2 CF3 2-SCH3 C(O)OCH3 *2
    11-074 3,5-Cl2 CF3 2-NO2 Br 179.0-181.0
    11-075 3,5-Cl2 CF3 2-NO2 C(O)OEt 160.0-162.0
    11-076 3,5-Cl2 CF3 2-NH2 Br *2
    11-077 3,5-Cl2 CF3 2-NH2 C(O)OH *2
    11-078 3,5-Cl2 CF3 2-NH2 C(O)OEt *2
    11-079 3,5-Cl2 CF3 2-Ph C(O)OH *1
    11-080 3,5-Cl2 CF3 2-Ph C(O)OCH3 *1
    11-081 3,5-Cl2 CF3 2,3-F2 CH3 *1
    11-082 3,5-Cl2 CF3 2,3-F2 CH2Br *1
    11-083 3,5-Cl2 CF3 2,3-F2 CH2OH *1
    11-084 3,5-Cl2 CF3 2,6-Cl2 C(O)OEt *2
    11-085 3,5-Cl2 CF3 2-Cl-6-CH3 NH2 *1
    11-086 3,5-Cl2 CF3 2,6-(CH3)2 OH 209.0-214.0
    11-087 3,5-Cl2 CF3 2,6-(CH3)2 OSO2CF3 nD 21. 6° C.1.5194
    11-088 3,5-Cl2 CF3 2,6-(CH3)2 C(O)OH 128.5-130.5
    11-089 3,5-Cl2 CF3 2,6-(CH3)2 C(O)OCH3 135.0-138.0
    11-090 3,5-Cl2 CF2Cl 2-Cl C(O)OH 100.0-104.5
    11-091 3,5-Cl2 CF2Cl 2-CH3 C(O)OH 76.0-80.0
    11-092 3,5-Cl2 CF2Cl 2-CH3 C(O)OEt *1
    11-093 3,5-Br2 CF3 2-Cl C(O)OH 144.5-147.0
    11-094 3,5-Br2 CF3 2-CH3 C(O)OH 135.0-138.5
    11-095 3,5-Br2 CF3 2-CH3 C(O)OEt *1
    11-096 3-OCH2O-4 CF3 — C(O)OH 208.0-210.0
    11-097 3-OCH2O-4 CF3 — C(O)OCH3 172.0-173.0
    11-098 3,5-Cl2 CF3 — Br 122.0-124.0
    11-099 3,5-Cl2 CF3 — I 144.0-146.0
    11-100 3,5-Cl2 CF3 — CH2Cl 98.0-100.0
    11-101 3,5-Cl2 CF3 2-F CH3 87.0-89.0
    11-102 3,5-Cl2 CF3 2-F CHBr2 *1
    11-103 3,5-Cl2 CF3 2-Cl CH3 97.0-99.0
    11-104 3,5-Cl2 CF3 2-Cl CH2Br 94.0-97.0
    11-105 3,5-Cl2 CF3 2-Cl CHBr2 *1
    11-106 3,5-Cl2 CF3 2-Cl CH2OH 32.0-35.0
    11-107 3,5-Cl2 CF3 2-Cl CH2OC(O)CH3 *1
    11-108 3,5-Cl2 CF3 2-Cl NO2 97.0-103.0
    11-109 3,5-Cl2 CF3 2-Cl NH2 158.0-160.0
    11-110 3,5-Cl2 CF3 2-Cl CHO 129.0-130.0
    11-111 3,5-Cl2 CF3 2-Br CH3 119.0-121.0
    11-112 3,5-Cl2 CF3 2-Br CHBr2 *1
    11-113 3,5-Cl2 CF3 2-Br CH2OH *1
    11-114 3,5-Cl2 CF3 2-Br CH2OC(O)CH3 *1
    11-115 3,5-Cl2 CF3 2-I CHBr2 125.0-128.0
    11-116 3,5-Cl2 CF3 2-I CHO *1
    11-117 3,5-Cl2 CF3 2-CH3 Cl 115.5-117.0
    11-118 3,5-Cl2 CF3 2-CH3 CH2Cl *1
    11-119 3,5-Cl2 CF3 2-CH3 CH2OH *1
    11-120 3,5-Cl2 CF3 2-CH3 CN 141.0-142.0
    11-121 3,5-Cl2 CF3 2-CH3 C(O)Cl 140.5-143.0
    11-122 3,5-Cl2 CF3 3-OH C(O)OEt *1
    11-123 3,5-Cl2 CF3 2-NO2 F 86.0-89.0
    11-124 3,5-(CF3)2 CF3 — NO2 170.0-172.0
    11-125 3,5-Cl2 CF3 2-OCHF2 NO2 *1
    11-126 3,5-Cl2 CF3 2-OCHF2 NH2 *1
    11-127 3,5-Cl2 CF3 2-OCHF2 I *1
    11-128 3,5-Cl2 CF3 2-NO2 CH3 119.0-122.0
    11-129 3-Cl-5-Br CF3 2-CH3 C(O)OEt *1
    11-130 3,5-(CF3)2 CF3 2-CH3 C(O)OEt *2
    11-131 3,5-Cl2 CF3 2-OH CH3 145.0-147.0
    11-132 3,5-Cl2 CF3 2-OCH3 CH3 86.0-89.0
  • TABLE 18
    Figure US20150105398A1-20150416-C00089
    No. (X)m R3 A1 A2 (Y)n R m.p. (° C.)
    12-001 3,5-Cl2 CF3 N C — Cl 139.0-140.0
    12-002 3,5-Cl2 CF3 N C — Br 147.0-148.0
    12-003 3,5-Cl2 CF3 N C — C(O)OH 118.0-120.0
    12-004 3,5-Cl2 CF3 N C — C(O)OEt 154.0-155.0
    12-005 3,5-Cl2 CF3 C N — C(O)OH 195.5-198.5
    12-006 3,5-Cl2 CF3 C N — C(O)OCH3 147.0-151.5
  • TABLE 19
    Figure US20150105398A1-20150416-C00090
    No. A1 (Y)n R2 R1 J m.p. (° C.)
    13-001 C — H CH2CF3 H 153.0-154.0
    13-002 C — H CH2CF3 Cl 158.0-160.0
    13-003 C — H CH2Ph H 191.0-192.0
    13-004 C — H CH2Ph Cl 131.0-133.0
    13-005 C — H CH2(D-47a) H 166.0-168.0
    13-006 C 2-CH3 H CH2CF3 H 190.5-194.0
    13-007 C 2-CH3 H CH2CF3 Cl 134.0-137.0
    13-008 C 2-CH3 H CH2(D-47a) H 163.0-164.0
    13-009 C 2-CH3 H CH2(D-47a) Cl 174.0-176.0
    13-010 C 3-CH3 H CH2CF3 H 163.0-168.0
  • TABLE 20
    Figure US20150105398A1-20150416-C00091
    No. X1 (X2)m1 R3 m.p./b.p. (° C.)
    14-001 Cl 5-Cl Pr-i nD 20. 6°C.1.5472
    14-002 Cl 5-Cl CHF2 nD 20. 6°C.1.5370
    14-003 Cl 5-Cl CF3 64.0-66.0/2mmHg
    14-004 Cl 5-Cl CF2Cl *2
    14-005 Cl 5-Cl CF2CF3 *2
    14-006 Cl 5-Cl CH2OCH2CF3 *2
    14-007 Cl 5-Cl CH2Si(CH3)3 *2
    14-008 Cl 5-Cl D-47a *2
    14-009 Cl 5-Br CF3 *2
    14-010 Cl 5-CH3 CF3 *2
    14-011 Cl 5-CH3-6-F CF3 nD 20. 6°C.1 .4895
    14-012 Cl 4-F-5-Cl CF3 *2
    14-013 Cl 4,5-Cl2 CF3 *1
    14-014 Cl 4-NHC(O)OBu-t-5-Cl CF3 67.0-68.0
    14-015 Br — CF3 nD 20. 7°C.1.5258
    14-016 Br 5-Br CF3 *2
    14-017 CF3 — CF3 nD 20. 6°C.1.4228
    14-018 CF3 5-Cl CF3 *2
    14-019 CF3 5-NO2 CF3 nD 20. 6°C.1.4553
    14-020 CF3 4-F-5-Cl CF3 *2
    14-021 T-4 — CF3 *2
    14-022 OCF2CHFOCF2CF2CF3 — CF3 *2
    14-023 OCH2Ph — CF3 *2
    14-024 OCH2(Ph-2-Cl) — CF3 *2
    14-025 O[(D-47f)-3-Cl-5-CF3] — CF3 *2
    14-026 SCF3 — CF3 *2
    14-027 NO2 — CF3 *2

    Among the compounds of the present invention, 1H NMR data of the compounds that the measured value of molecular ion peak, melting point or refractive index is not shown are shown in Table 21.
    In the meantime, the indication of “(A)” in the table shows a condition in which tetramethylsilane is used as standard substance in chloroform-d solvent and measurement is carried out at 300 MHz (CDCl3, Me4Si, 300 MHz), hereinafter, the indication “(B)” shows the measurement condition of (CDCl3, Me4Si, 400 MHz), the indication of “(C)” shows the measurement condition of (CDCl3-DMSO-d6, Me4Si, 300 MHz), and the indication of “(D)” shows the measurement condition of (CDCl3-DMSO-d6, Me4Si, 400 MHz).
  • TABLE 21
    No. 1H NMR
    3-010 (A) δ 8.55-8.6 (m, 1H), 7.15-8.05 (m, 15H), 6.95-7.1 (m, 1H),
    5.20 (s, 2H), 4.76 (d, J = 4.4 Hz, 2H), 4.10 (d, J = 17.2 Hz, 1H),
    3.78 (d, J = 17.2 Hz, 1H).
    3-034 (A) δ 7.2-7.5 (m, 7H), 4.55-4.7 (m, 2H), 4.06 (d, J = 17.1 Hz, 1H),
    3.67 (d, J = 17.1 Hz, 1H), 2.38 (s, 3H).
    3-059 (B) δ 7.9-7.95 (m, 2H), 7.8-7.9 (m, 1H), 7.7-7.8 (m, 2H), 7.51 (s, 2H),
    7.4-7.45 (m, 1H), 5.02 (d, J = 7.0 Hz, 2H), 4.12 (d, J = 17.0 Hz, 1H),
    3.73 (d, J = 17.0 Hz, 1H).
    3-064 (A) δ 7.84 (d, J = 8.4 Hz, 2H), 7.74 (d, J = 8.4 Hz, 2H), 7.51 (bs, 2H),
    7.43 (bs, 1H), 6.42 (bs, 1H), 4.63 (t, J = 5.1 Hz, 1H),
    4.11 (d, J = 17.4 Hz, 1H), 3.65-3.85 (m, 3H), 3.5-3.65 (m, 4H),
    1.24 (t, J = 6.8 Hz, 6H).
    3-067 (A) δ 7.6-7.8 (m, 3H), 7.54 (d, J = 7.8 Hz, 2H), 7.44 (bs, 2H),
    7.38 (bs, 1H), 3.4-4.25 (m, 7H), 4.04 (d, J = 17.7 Hz, 1H),
    3.69 (d, J = 17.4 Hz, 1H).
    3-069 (A) δ 7.82 (d, J = 8.7 Hz, 2H), 7.71 (d, J = 8.7 Hz, 2H), 7.51 (bs, 2H),
    7.42 (bs, 1H), 6.71 (bs, 1H), 4.11 (d, J = 17.4 Hz, 1H), 3.6-3.95 (m, 4H),
    3.74 (d, J = 17.1 Hz, 1H), 3.48 (t, J = 6.3 Hz, 2H), 2.55-2.7 (m, 1H),
    2.0-2.15 (m, 1H), 1.6-1.75 (m, 1H).
    3-072 (A) δ 7.85 (d, J = 8.4 Hz, 2H), 7.73 (d, J = 8.4 Hz, 2H), 7.51 (bs, 2H),
    7.4-7.5 (m, 1H), 6.44 (bs, 1H), 4.75 (t, J = 4.8 Hz, 1H), 4.1-4.2 (m, 2H),
    4.10 (d, J = 17.4 Hz, 1H), 3.75-3.9 and 3.6-3.65 (m, 2H),
    3.72 (d, J = 17.4 Hz, 1H), 3.6-3.65 (m, 2H), 2.0-2.15 (m, 1H),
    1.35-1.45 (m, 1H).
    3-074 (A) δ 7.82 (d, J = 8.4 Hz, 2H), 7.72 (d, J = 8.4 Hz, 2H), 7.51 (bs, 2H),
    7.4-7.45 (m, 1H), 6.53 (bs, 1H), 4.09 (d, J = 17.4 Hz, 1H), 3.72 (s, 2H),
    3.71 (d, J = 17.4 Hz, 1H), 2.92 (s, 3H), 1.72 (s, 6H).
    3-077 (A) δ 9.79 (s, 1H), 7.89 (d, J = 8.4 Hz, 2H), 7.76 (d, J = 8.4 Hz, 2H),
    7.61 (bs, 2H), 7.51 (bs, 1H), 6.91 (bs, 1H), 4.46 (d, J = 4.5 Hz, 2H),
    4.11 (d, J = 17.4 Hz, 1H), 3.72 (d, J = 17.1 Hz, 1H).
    3-078 (A) δ 9.27 (bs, 1H), 7.85 (d, J = 8.5 Hz, 2H), 7.74 (d, J = 8.7 Hz, 2H),
    7.60 and 6.93 (t, J = 4.4 Hz, 1H), 7.51 (bs, 2H), 7.44 (bs, 1H),
    6.71 (bs, 1H), 4.37 and 4.26 (d, J = 4.7 Hz, 2H), 4.11 (d, J = 16.8 Hz, 1H),
    3.72 (d, J = 17.4 Hz, 1H).
    3-079 (A) δ 7.8-7.9 (m, 2H), 7.7-7.8 (m, 2H), 7.45-7.55 (m, 2H),
    7.45-7.55 and 6.82 (t, J = 4.4 Hz, 1H), 7.43 (t, J = 2.0 Hz, 1H),
    6.71 and 6.60 (bs, 1H), 4.31 and 4.24 (t, J = 4.5 Hz, 2H),
    4.11 (d, J = 17.4 Hz, 1H), 3.94 and 3.88 (s, 3H), 3.72 (d, J = 17.4 Hz, 1H).
    3-082 (A) δ 7.90 (d, J = 8.7 Hz, 2H), 7.73 (d, J = 8.7 Hz, 2H), 7.52 (s, 2H),
    7.43 (s, 1H), 7.10 (t, J = 4.8 Hz, 1H), 4.21 (d, J = 4.8 Hz, 2H),
    4.12 (d, J = 17.4 Hz, 1H), 3.74 (d, J = 17.4 Hz, 1H).
    3-083 (A) δ 7.87 (d, J = 8.1 Hz, 2H), 7.74 (d, J = 8.1 Hz, 2H), 7.52 (s, 2H),
    7.43 (s, 1H), 6.73 (bs, 1H), 4.26 (d, J = 5.1 Hz, 2H),
    4.11 (d, J = 17.4 Hz, 1H), 3.82 (s, 3H), 3.73 (d, J = 17.4 Hz, 1H).
    3-087 (A) δ 8.52 (bs, 1H), 7.97 (bs, 1H), 7.88 (d, J = 8.4 Hz, 2H),
    7.7-7.8 (m, 3H), 7.51 (s, 2H), 7.43 (s, 1H), 4.45 (d, J = 4.8 Hz, 2H),
    4.11 (d, J = 17.4 Hz, 1H), 3.74 (d, J = 17.4 Hz, 1H).
    3-089 (A) δ 7.84 (d, J = 8.5 Hz, 2H), 7.73 (d, J = 8.5 Hz, 2H), 7.51 (bs, 2H),
    7.43 (bs, 1H), 6.18 (bs, 1H), 5.85-6.05 (m, 1H), 5.2-5.35 (m, 2H),
    4.05-4.15 (m, 3H), 3.72 (d, J = 17.4 Hz, 1H).
    3-107 (A) δ 7.82 (d, J = 8.1 Hz, 2H), 7.72 (d, J = 8.4 Hz, 2H), 7.55 (s, 1H),
    7.51 (bs, 2H), 7.43 (bs, 1H), 6.27 (bs, 1H), 4.48 (d, J = 5.1 Hz, 2H),
    4.10 (d, J = 17.1 Hz, 1H), 3.79 (s, 3H), 3.71 (d, J = 17.4 Hz, 1H).
    3-108 (A) δ 7.82 (d, J = 8.1 Hz, 2H), 7.72 (d, J = 8.4 Hz, 2H), 7.51 (bs, 2H),
    7.4-7.45 (m, 1H), 6.34 (bs, 1H), 4.48 (d, J = 5.4 Hz, 2H),
    4.10 (d, J = 17.1 Hz, 1H), 3.81 (s, 3H), 3.71 (d, J = 17.4 Hz, 1H).
    3-110 (A) δ 7.82 (d, J = 8.1 Hz, 2H), 7.74 (d, J = 8.7 Hz, 2H), 7.51 (bs, 2H),
    7.43 (bs, 1H), 6.36 (bs, 1H), 6.17 (s, 1H), 4.65 (d, J = 5.7 Hz, 2H),
    4.08 (d, J = 17.1 Hz, 1H), 3.85 (s, 3H), 3.69 (d, J = 17.4 Hz, 1H).
    3-114 (A) δ 7.86 (d, J = 8.1 Hz, 2H), 7.71 (d, J = 8.4 Hz, 2H), 7.51 (bs, 2H),
    7.4-7.45 (m, 2H), 7.08 (s, 1H), 6.98 (bs, 1H), 4.68 (d, J = 5.4 Hz, 2H),
    4.07 (d, J = 17.4 Hz, 1H), 3.68 (d, J = 17.4 Hz, 1H), 2.72 (s, 3H).
    3-118 (D) δ 7.95-8.0 (m, 2H), 7.75-7.8 (m, 2H), 7.35-7.55 (m, 4H),
    5.45-5.5 (m, 2H), 4.15-4.2 (m, 1H), 3.8-3.85 (m, 1H), 2.57 (s, 3H).
    3-119 (B) δ 8.55-8.65 (m, 1H), 7.91 (d, J = 8.2 Hz, 2H), 7.65 (d, J = 8.2 Hz, 2H),
    7.50 (s, 2H), 7.42 (s, 1H), 6.91 (s, 1H), 6.86 (s, 1H),
    4.67 (d, J = 5.3 Hz, 2H), 4.08 (d, J = 17.0 Hz, 1H), 3.77 (s, 3H),
    3.70 (d, J = 17.0 Hz, 1H).
    3-120 (B) δ 7.35-8.0 (m, 8H), 6.95 (m, 2H), 6.6-6.75 (m, 2H),
    4.08 (d, J = 17.0 Hz, 1H), 3.70 (d, J = 17.0 Hz, 1H), 3.63 (s, 3H).
    3-121 (B) δ 8.1-8.2 (m, 1H), 7.65-7.9 (m, 3H), 7.4-7.6 (m, 3H), 7.1-7.2 (m, 1H),
    4.86 (d, J = 5.8 Hz, 2H), 4.05-4.15 (m, 1H), 3.65-3.8 (m, 1H),
    2.72 (s, 3H).
    3-122 (A) δ 8.43 (s, 1H), 7.88 (d, J = 8.1 Hz, 2H), 7.72 (d, J = 8.1 Hz, 2H),
    7.51 (s, 2H), 7.44 (s, 1H), 7.30 (t, J = 5.4 Hz, 1H), 4.93 (d, J = 5.4 Hz, 2H),
    4.10 (d, J = 17.1 Hz, 1H), 3.72 (d, J = 17.1 Hz, 1H).
    3-127 (B) δ 7.93 (d, J = 8.2 Hz, 2H), 7.82 (t, J = 4.8 Hz, 1H), 7.74 (d, J = 8.2 Hz, 2H),
    7.58 (t, J = 7.7 Hz, 1H), 7.5-7.55 (m, 2H), 7.43 (t, J = 1.8 Hz, 1H),
    7.16 (d, J = 7.7 Hz, 1H), 7.09 (d, J = 7.7 Hz, 1H), 4.71 (d, J = 4.8 Hz, 2H),
    3.93 (d, J = 17.2 Hz, 1H), 3.74 (d, J = 17.4 Hz, 1H), 2.57 (s, 3H).
    3-131 (A) δ 8.55 (s, 1H), 8.40 (s, 1H), 7.91 (d, J = 8.2 Hz, 2H),
    7.72 (d, J = 8.2 Hz, 2H), 7.53 (s, 3H), 7.42 (s, 1H), 4.7-4.8 (m, 2H),
    4.13 (d, J = 17.0 Hz, 1H), 3.74 (d, J = 17.0 Hz, 1H), 2.57 (s, 3H).
    3-134 (A) δ 9.64 (bs, 1H), 7.81 (d, J = 8.1 Hz, 2H), 7.69 (d, J = 8.1 Hz, 2H),
    7.50 (s, 2H), 7.43 (s, 1H), 4.10 (d, J = 17.4 Hz, 1H), 3.86 (s, 3H),
    3.73 (d, J = 17.4 Hz, 1H).
    3-135 (A) δ 8.19 (d, J = 4.2 Hz, 1H), 7.95 (d, J = 8.4 Hz, 2H), 7.76 (d, J = 8.4 Hz, 2H),
    7.5-7.6 (m, 4H), 7.44 (s, 1H), 7.10 (bs, 1H), 6.84 (t, J = 8.4 Hz, 1H),
    6.78 (d, J = 8.4 Hz, 1H), 4.11 (d, J = 17.4 Hz, 1H), 3.73 (d, J = 17.4 Hz, 1H).
    3-143 (A) δ 8.57 (d, J = 5.1 Hz, 1H), 8.21 (bs, 1H), 7.85-8.05 (m, 2H),
    7.6-7.8 (m, 3H), 7.15-7.45 (m, 5H), 4.72 (d, J = 5.1 Hz, 2H),
    4.10 (d, J = 17.4 Hz, 1H), 3.76 (d, J = 17.4 Hz, 1H), 2.38 (s, 3H).
    3-147 (A) δ 7.86 (d, J = 8.5 Hz, 2H), 7.77 (d, J = 8.5 Hz, 2H), 7.55-7.65 (m, 1H),
    7.2-7.3 (m, 1H), 4.05-4.25 (m, 3H), 3.86 (d, J = 17.0 Hz, 1H), 2.30 (s, 3H).
    4-003 (A) δ 8.5-8.7 (m, 1H), 7.35-7.9 (m, 9H), 7.1-7.3 (m, 1H), 4.5-5.1 (m, 4H),
    4.0-4.2 (m, 1H), 3.6-3.8 (m, 1H), 3.15-3.55 (m, 3H).
    4-004 (A) δ 8.55-8.65 (m, 1H), 7.35-7.8 (m, 9H), 7.1-7.3 (m, 1H),
    4.6-5.15 (m, 4H), 3.3-4.2 (m, 4H), 1.1-1.35 (m, 3H).
    4-005 (A) δ 8.2-8.3 (m, 1H), 7.15-7.8 (m, 10H), 4.75-5.35 (m, 4H),
    4.08 (d, J = 17.0 Hz, 1H), 3.70 (d, J = 17.0 Hz, 1H), 3.04 and 2.84 (bs, 3H).
    4-006 (B) δ 8.5-8.6 (m, 1H), 7.1-7.75 (m, 10H), 5.65-5.95 (m, 1H),
    5.1-5.3 (m, 2H), 4.85 and 4.53 (s, 2H), 3.6-4.2 (m, 4H).
    4-007 (B) δ 8.5-8.7 (m, 1H), 6.95-7.75 (m, 10H), 5.65-6.1 (m, 2H),
    5.1-5.45 (m, 4H), 4.4-4.9 (m, 4H), 3.75-4.2 (m, 3H).
    4-008 (A) δ 8.50 (bs, 1H), 7.0-7.75 (m, 15H), 4.35-4.9 (m, 4H),
    4.05 (d, J = 17.0 Hz, 1H), 3.68 (d, J = 17.0 Hz, 1H).
    4-009 (A) δ 8.5-8.55 (m, 1H), 7.65-7.75 (m, 5H), 7.51 (s, 2H), 7.42 (s, 1H),
    7.25-7.3 (m, 1H), 7.15-7.25 (m, 1H), 5.17 (s, 2H),
    4.10 (d, J = 17.0 Hz, 1H), 3.71 (d, J = 17.0 Hz, 1H), 3.60 (s, 3H).
    4-010 (A) δ 8.37 (bs, 1H), 7.65-7.8 (m, 3H), 7.3-7.55 (m, 6H), 4.4-4.9 (m, 2H),
    4.10 (d, J = 17.0 Hz, 1H), 3.70 (d, J = 17.0 Hz, 1H), 3.1-3.65 (m, 2H),
    1.12 (bs, 3H).
    4-011 (B) δ 7.7-7.8 (m, 4H), 7.52 (s, 2H), 7.43 (s, 1H), 4.10 (d, J = 17.0 Hz, 1H),
    3.72 (d, J = 17.0 Hz, 1H), 3.53 (s, 3H), 3.37 (s, 3H).
    5-001 (A) δ 8.51 (d, J = 4.8 Hz, 1H), 7.69 (t, J = 5.1 Hz, 1H), 7.62 (s, 1H),
    7.45-7.55 (m, 2H), 7.25-7.4 (m, 4H), 7.22 (dd, J = 6.9, 2.5 Hz, 1H),
    4.73 (d, J = 5.1 Hz, 2H), 4.09 (d, J = 16.8 Hz, 1H), 3.73 (d, J = 16.8 Hz, 1H),
    2.48 (s, 3H).
    5-003 (A) δ 8.51 (d, J = 4.8 Hz, 1H), 7.77 (s, 1H), 7.68 (t, J = 4.5 Hz, 1H),
    7.45-7.6 (m, 5H), 7.25-7.35 (m, 3H), 7.22 (dd, J = 7.5, 1.8 Hz, 1H),
    4.73 (d, J = 4.5 Hz, 2H), 4.09 (d, J = 17.4 Hz, 1H), 3.73 (d, J = 17.4 Hz, 1H),
    2.49 (s, 3H).
    5-007 (A) δ 8.52 (d, J = 4.2 Hz, 1H), 7.78 (d, J = 9.3 Hz, 2H), 7.67 (t, J = 5.1 Hz, 1H),
    7.51 (bs, 3H), 7.3-7.4 (m, 4H), 7.15-7.25 (m, 1H),
    4.73 (d, J = 5.1 Hz, 2H), 4.07 (d, J = 17.4 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H),
    2.48 (s, 3H).
    5-009 (A) δ 8.51 (d, J = 4.5 Hz, 1H), 7.89 (bs, 1H), 7.82 (d, J = 7.8 Hz, 1H),
    7.65-7.75 (m, 2H), 7.60 (t, J = 7.8 Hz, 1H), 7.5-7.55 (m, 3H),
    7.33 (bs, 1H), 7.32 (d, J = 7.8 Hz, 1H), 7.21 (dd, J = 7.2, 1.5 Hz, 1H),
    4.73 (d, J = 5.1 Hz, 2H), 4.15 (d, J = 17.4 Hz, 1H), 3.77 (d, J = 17.4 Hz, 1H),
    2.49 (s, 3H).
    5-010 (A) δ 7.25-7.6 (m, 7H), 6.37 (bs, 1H), 4.0-4.15 (m, 2H),
    4.11 (d, J = 17.4 Hz, 1H), 3.77 and 3.75 (d, J = 17.4 Hz, 1H),
    2.95 (dd, J = 10.2, 8.7 Hz, 1H), 2.41 (s, 3H), 2.03 (dd, J = 10.2, 3.3 Hz, 1H),
    1.90 (dd, J = 8.7, 3.3 Hz, 1H).
    5-011 (A) δ 8.51 (d, J = 4.2 Hz, 1H), 7.69 (t, J = 4.8 Hz, 1H), 7.15-7.6 (m, 10H),
    4.72 (d, J = 4.8 Hz, 2H), 4.10 (d, J = 17.1 Hz, 1H),
    3.77 (dd, J = 17.1, 3.0 Hz, 1H), 2.95 (dd, J = 10.2, 8.4 Hz, 1H), 2.48 (s, 3H),
    2.02 (dd, J = 10.2, 3.0 Hz, 1H), 1.89 (dd, J = 8.4, 3.0 Hz, 1H).
    5-012 (A) δ 7.25-7.5 (m, 7H), 7.16 (bs, 1H), 4.0-4.2 (m, 3H),
    3.75 (d, J = 17.2 Hz, 1H), 2.42 (s, 3H).
    5-013 (A) δ 8.5-8.6 (m, 1H), 7.65-7.8 (m, 1H), 7.15-7.6 (m, 10H),
    4.72 (d, J = 5.2 Hz, 2H), 4.12 (d, J = 17.3 Hz, 1H), 3.74 (d, J = 17.3 Hz, 1H),
    2.46 (s, 3H).
    5-015 (B) δ 8.5-8.55 (m, 1H), 7.72 (td, J = 6.8, 4.8 Hz, 1H), 7.45-7.6 (m, 5H),
    7.2-7.4 (m, 5H), 4.75 (d, J = 4.8 Hz, 2H), 4.11 (d, J = 17.2 Hz, 1H),
    3.74 (d, J = 17.2 Hz, 1H), 2.50 (s, 3H).
    5-016 (A) δ 7.35-7.6 (m, 6H), 7.2-7.3 (m, 1H), 6.10 (d, J = 53.4 Hz, 1H),
    6.06 (bs, 1H), 4.0-4.2 (m, 3H), 3.72 (d, J = 16.8 Hz, 1H), 2.47 (s, 3H).
    5-017 (A) δ 8.54 (d, J = 4.8 Hz, 1H), 7.65-7.75 (m, 1H), 7.35-7.6 (m, 6H),
    7.2-7.35 (m, 4H), 6.10 (d, J = 53.1 Hz, 1H), 4.75 (d, J = 5.1 Hz, 2H),
    4.11 (d, J = 17.4 Hz, 1H), 3.73 (d, J = 17.4 Hz, 1H), 2.50 (s, 3H).
    5-018 (A) δ 8.45-8.55 (m, 1H), 7.15-7.75 (m, 14H), 6.95-7.05 (m, 1H),
    5.19 (s, 2H), 4.74 (d, J = 4.4 Hz, 2H), 4.07 (d, J = 16.8 Hz, 1H),
    3.75 (d, J = 16.8 Hz, 1H), 2.49 (s, 3H).
    5-019 (A) δ 8.24 (s, 1H), 8.00 (s, 1H), 7.2-7.6 (m, 6H), 7.2-7.3 (m, 1H),
    6.44 (t, J = 6.5 Hz, 1H), 3.95-4.15 (m, 2H), 4.09 (d, J = 17.1 Hz, 1H),
    3.78 (d, J = 17.1 Hz, 1H), 2.40 (s, 3H).
    5-020 (A) δ 8.52 (d, J = 4.8 Hz, 1H), 8.25 (s, 1H), 8.00 (s, 1H),
    7.45-7.75 (m, 7H), 7.15-7.35 (m, 4H), 4.74 (d, J = 4.8 Hz, 2H),
    4.10 (d, J = 17.4 Hz, 1H), 3.78 (d, J = 17.4 Hz, 1H), 2.49 (s, 3H).
    5-021 (A) δ 8.51 (d, J = 4.5 Hz, 1H), 7.69 (t, J = 5.1 Hz, 1H), 7.5-7.6 (m, 4H),
    7.25-7.4 (m, 5H), 7.21 (dd, J = 7.2, 1.5 Hz, 1H), 4.73 (d, J = 5.1 Hz, 2H),
    4.08 (d, J = 17.4 Hz, 1H), 3.74 (d, J = 17.4 Hz, 1H), 2.98 (q, J = 7.2 Hz, 2H),
    2.48 (s, 3H), 1.33 (t, J = 7.2 Hz, 3H).
    5-022 (A) δ 7.89 (s, 1H), 7.7-7.8 (m, 2H), 7.5-7.6 (m, 3H),
    7.45 (d, J = 8.0 Hz, 1H), 6.06 (t, J = 6.2 Hz, 1H), 4.0-4.2 (m, 3H),
    3.73 (d, J = 16.6 Hz, 1H), 2.47 (s, 3H).
    5-023 (A) δ 8.55 (d, J = 4.7 Hz, 1H), 7.90 (s, 1H), 7.65-7.8 (m, 3H),
    7.5-7.6 (m, 4H), 7.3-7.45 (m, 2H), 7.2-7.3 (m, 1H),
    4.74 (d, J = 5.0 Hz, 2H), 4.12 (d, J = 17.1 Hz, 1H), 3.73 (d, J = 17.1 Hz, 1H),
    2.49 (s, 3H).
    5-024 (B) δ 7.65 (d, J = 8.1 Hz, 1H), 7.45-7.6 (m, 4H), 7.40 (d, J = 7.9 Hz, 1H),
    7.34 (d, J = 7.7 Hz, 1H), 6.35 (bs, 1H), 4.0-4.15 (m, 3H),
    3.73 (d, J = 17.2 Hz, 1H), 3.37 (s, 3H), 2.43 (s, 3H).
    5-025 (B) δ 8.5-8.55 (m, 1H), 7.71 (td, J = 7.7, 1.6 Hz, 1H), 7.3-7.7 (m, 7H),
    7.28 (d, J = 4.6 Hz, 1H), 7.26 (t, J = 4.8 Hz, 1H),
    7.23 (dd, J = 7.5, 5.9 Hz, 1H), 4.75 (d, J = 4.8 Hz, 2H),
    4.12 (d, J = 17.2 Hz, 1H), 3.73 (d, J = 17.2 Hz, 1H), 3.39 (s, 3H),
    2.50 (s, 3H).
    5-026 (B) δ 7.4-7.65 (m, 6H), 7.36 (d, J = 7.9 Hz, 1H), 6.34 (t, J = 6.1 Hz, 1H),
    4.11 (d, J = 17.2 Hz, 1H), 4.08 (qd, J = 9.6, 6.6 Hz, 2H),
    3.73 (d, J = 17.4 Hz, 1H), 3.50 (d, J = 0.9 Hz, 3H), 2.41 (s, 3H).
    5-027 (B) δ 8.53 (ddd, J = 4.9, 1.6, 0.9 Hz, 1H), 7.70 (td, J = 7.7, 1.8 Hz, 1H),
    7.6-7.65 (m, 2H), 7.5-7.55 (m, 4H), 7.44 (ddd, J = 7.9, 2.0, 1.3 Hz, 1H),
    7.33 (d, J = 7.7 Hz, 1H), 7.26 (t, J = 4.8 Hz, 1H),
    7.22 (ddd, J = 7.5, 4.8, 1.1 Hz, 1H), 4.75 (d, J = 4.8 Hz, 2H),
    4.12 (d, J = 17.2 Hz, 1H), 3.74 (d, J = 17.2 Hz, 1H), 3.51 (s, 3H),
    2.49 (s, 3H).
    5-028 (B) δ 8.5-8.55 (m, 1H), 7.83 (bs, 1H), 7.2-7.75 (m, 15H),
    4.76 (d, J = 4.8 Hz, 2H), 4.13 (dd, J = 17.2, 1.8 Hz, 1H),
    3.82 (d, J = 17.2 Hz, 1H), 2.51 (s, 3H).
    5-029 (A) δ 8.51 (d, J = 4.5 Hz, 1H), 7.69 (t, J = 5.1 Hz, 1H), 7.51 (bs, 2H),
    7.50 (bs, 1H), 7.15-7.4 (m, 5H), 6.8-6.95 (m, 1H), 4.74 (d, J = 4.8 Hz, 2H),
    4.07 (d, J = 17.4 Hz, 1H), 3.72 (d, J = 17.4 Hz, 1H), 2.48 (s, 3H).
    5-030 (A) δ 7.2-7.45 (m, 6H), 6.49 (bs, 1H), 4.0-4.15 (m, 2H), 3.46 (s, 2H),
    2.40 (s, 3H), 1.79 (s, 3H).
    5-031 (A) δ 7.25-7.5 (m, 6H), 6.50 (bs, 1H), 4.0-4.15 (m, 2H),
    3.60 (d, J = 16.8 Hz, 1H), 3.39 (d, J = 16.8 Hz, 1H), 2.38 (s, 3H),
    2.15-2.3 (m, 1H), 0.98 (d, J = 6.6 Hz, 3H), 0.90 (d, J = 6.9 Hz, 3H).
    5-033 (A) δ 8.51 (d, J = 4.8 Hz, 1H), 7.69 (t, J = 4.5 Hz, 1H), 7.45-7.5 (m, 3H),
    7.41 (bs, 2H), 7.15-7.4 (m, 4H), 4.73 (d, J = 4.5 Hz, 2H),
    3.57 (d, J = 16.8 Hz, 1H), 3.47 (d, J = 16.8 Hz, 1H), 2.48 (s, 3H),
    1.35-1.5 (m, 1H), 0.45-0.7 (m, 4H).
    5-035 (B) δ 8.5-8.55 (m, 1H), 7.72 (td, J = 7.6, 1.8 Hz, 1H), 7.5-7.55 (m, 4H),
    7.43 (d, J = 1.8 Hz, 2H), 7.35-7.4 (m, 2H), 7.2-7.25 (m, 1H),
    4.76 (d, J = 4.8 Hz, 2H), 3.93 (d, J = 16.8 Hz, 1H),
    3.85 (dd, J = 18.6, 11.8 Hz, 2H), 3.53 (d, J = 16.8 Hz, 1H), 2.50 (s, 3H).
    5-037 (A) δ 8.53 (d, J = 5.0 Hz, 1H), 7.65-7.75 (m, 1H), 7.15-7.6 (m, 9H),
    5.89 (t, J = 55.2 Hz, 1H), 4.74 (d, J = 4.7 Hz, 2H), 4.00 (d, J = 17.0 Hz, 1H),
    3.55 (d, J = 17.0 Hz, 1H), 2.50 (s, 3H).
    5-038 (B) δ 8.17 (t, J = 7.0 Hz, 1H), 7.45-7.6 (m, 4H), 7.44 (t, J = 1.8 Hz, 1H),
    7.0-7.1 (m, 1H), 4.05-4.25 (m, 3H), 3.73 (d, J = 17.4 Hz, 1H).
    5-040 (A) δ 8.82 (s, 1H), 8.19 (t, J = 7.8 Hz, 1H), 7.4-7.6 (m, 6H), 7.31 (s, 1H),
    4.84 (d, J = 5.4 Hz, 2H), 4.08 (d, J = 17.4 Hz, 1H), 3.69 (d, J = 17.1 Hz, 1H).
    5-042 (B) δ 8.03 (m, 1H), 7.64 (d, J = 1.1 Hz, 1H), 7.58 (d, J = 0.8 Hz, 1H),
    7.50 (s, 2H), 7.43 (bs, 1H), 6.39 (bs, 1H), 4.18 (d, J = 16.0 Hz, 1H),
    4.1-4.2 (m, 2H), 3.80 (d, J = 16.0 Hz, 1H).
    5-048 (A) δ 8.22 (d, J = 8.7 Hz, 2H), 7.81 (d, J = 7.8 Hz, 1H), 7.74 (d, J = 1.2 Hz, 1H),
    7.63 (dd, J = 8.4, 1.8 Hz, 1H), 7.54 (d, J = 8.7 Hz, 2H), 7.50 (bs, 2H),
    7.44 (d, J = 2.1 Hz, 1H), 6.72 (bs, 1H), 4.77 (d, J = 6.3 Hz, 2H),
    4.04 (d, J = 17.1 Hz, 1H), 3.66 (d, J = 17.1 Hz, 1H).
    5-049 (A) δ 7.81 (d, J = 8.1 Hz, 1H), 7.7-7.75 (m, 2H),
    7.63 (dd, J = 8.1, 1.8 Hz, 1H), 7.50 (bs, 2H), 7.44 (bs, 1H),
    7.34 (d, J = 3.3 Hz, 1H), 7.16 (bs, 1H), 5.00 (d, J = 5.4 Hz, 2H),
    4.06 (d, J = 17.1 Hz, 1H), 3.69 (d, J = 17.1 Hz, 1H).
    5-050 (A) δ 8.79 (s, 1H), 7.75 (dd, J = 8.4, 3.0 Hz, 1H), 7.70 (bs, 1H),
    7.60 (bs, 1H), 7.50 (bs, 2H), 7.44 (bs, 1H), 7.33 (s, 1H), 7.01 (bs, 1H),
    4.82 (d, J = 5.1 Hz, 2H), 4.07 (d, J = 17.4 Hz, 1H), 3.69 (d, J = 17.1 Hz, 1H).
    5-051 (A) δ 7.7-7.8 (m, 2H), 7.61 (dd, J = 8.1, 1.5 Hz, 1H), 7.50 (bs, 2H),
    7.44 (bs, 1H), 7.19 (s, 1H), 6.84 (bs, 1H), 4.69 (d, J = 5.7 Hz, 2H),
    4.07 (d, J = 17.4 Hz, 1H), 3.69 (d, J = 17.4 Hz, 1H).
    5-052 (B) δ 8.63 (s, 1H), 7.25-7.75 (m, 7H), 5.10 (d, J = 5.8 Hz, 2H),
    4.07 (d, J = 17.0 Hz, 1H), 3.71 (d, J = 17.0 Hz, 1H).
    5-053 (A) δ 8.54 (d, J = 4.2 Hz, 1H), 7.77 (d, J = 7.8 Hz, 1H), 7.6-7.8 (m, 3H),
    7.62 (d, J = 7.8 Hz, 1H), 7.50 (bs, 2H), 7.44 (bs, 1H),
    7.34 (d, J = 7.5 Hz, 1H), 7.23 (dd, J = 7.5, 2.4 Hz, 1H),
    4.78 (d, J = 4.5 Hz, 2H), 4.08 (d, J = 18.0 Hz, 1H), 3.71 (d, J = 18.0 Hz, 1H).
    5-056 (A) δ 8.55 (d, J = 4.5 Hz, 1H), 8.08 (t, J = 4.5 Hz, 1H), 7.96 (s, 1H),
    7.78 (d, J = 8.4 Hz, 1H), 7.72 (d, J = 8.4 Hz, 1H),
    7.69 (dd, J = 4.5, 2.4 Hz, 1H), 7.50 (bs, 2H), 7.43 (bs, 1H),
    7.33 (d, J = 7.2 Hz, 1H), 7.23 (dd, J = 7.2, 2.4 Hz, 1H),
    4.73 (d, J = 4.5 Hz, 2H), 4.28 (d, J = 18.0 Hz, 1H), 3.87 (d, J = 18.0 Hz, 1H).
    5-058 (B) δ 8.54 (d, J = 3.9 Hz, 1H), 7.89 (bs, 1H), 7.74 (td, J = 7.8, 1.8 Hz, 1H),
    7.6-7.7 (m, 1H), 7.50 (bs, 3H), 7.44 (t, J = 1.8 Hz, 1H),
    7.38 (d, J = 7.8 Hz, 1H), 7.2-7.3 (bs, 1H), 4.79 (d, J = 4.7 Hz, 2H),
    4.07 (d, J = 17.2 Hz, 1H), 3.70 (d, J = 17.2 Hz, 1H).
    5-060 (B) δ 8.01 (bs, 1H), 7.65-7.75 (m, 2H), 7.50 (bs, 2H), 7.4-7.45 (m, 1H),
    6.25-6.3 (m, 1H), 4.06 (d, J = 17.2 Hz, 1H), 3.55-3.75 (m, 3H),
    3.45-3.6 (m, 4H), 1.20 (t, J = 7.0 Hz, 3H).
    5-061 (B) δ 8.10 (bs, 1H), 7.69 (d, J = 8.0 Hz, 1H), 7.50 (bs, 2H),
    7.4-7.45 (m, 2H), 6.09 (bs, 1H), 4.54 (t, J = 5.2 Hz, 1H),
    4.06 (d, J = 17.2 Hz, 1H), 3.69 (d, J = 17.2 Hz, 1H), 3.60 (t, J = 5.2 Hz, 2H),
    3.44 (s, 6H).
    5-062 (B) δ 8.13 (bs, 1H), 7.71 (d, J = 8.0 Hz, 1H), 7.4-7.5 (m, 4H),
    6.7-6.9 (br, 1H), 6.05-6.3 (br, 1H), 4.05-4.15 (m, 2H),
    4.06 (d, J = 17.2 Hz, 1H), 3.69 (d, J = 17.2 Hz, 1H), 2.88 (bs, 3H).
    5-065 (B) δ 8.5-8.55 (m, 1H), 8.13 (d, J = 1.8 Hz, 1H), 7.7-7.5 (m, 2H),
    7.50 (d, J = 1.8 Hz, 2H), 7.44 (t, J = 1.8 Hz, 1H), 7.37 (d, J = 8.0 Hz, 1H),
    7.2-7.3 (m, 3H), 4.78 (d, J = 4.8 Hz, 2H), 4.06 (d, J = 17.2 Hz, 1H),
    3.68 (d, J = 17.2 Hz, 1H).
    5-070 (A) δ 7.35-7.55 (m, 6H), 6.02 (bs, 1H), 4.09 (d, J = 17.4 Hz, 1H),
    3.71 (d, J = 17.4 Hz, 1H), 3.25-3.35 (m, 2H), 2.45 (s, 3H),
    1.0-1.15 (m, 1H), 0.55-0.65 (m, 2H), 0.25-0.35 (m, 2H).
    5-072 (A) δ 7.35-7.55 (m, 6H), 5.78 (bs, 1H), 4.08 (d, J = 17.0 Hz, 1H),
    3.69 (d, J = 17.0 Hz, 1H), 3.47 (t, J = 7.1 Hz, 2H), 2.45-2.65 (m, 1H),
    2.44 (s, 3H), 1.65-2.2 (m, 6H).
    5-077 (A) δ 7.4-7.5 (m, 6H), 6.19 (bs, 1H), 4.08 (d, J = 16.8 Hz, 1H),
    3.5-3.75 (m, 7H), 2.47 (s, 3H), 1.20 (t, J = 6.9 Hz, 3H).
    5-079 (B) δ 7.45-7.55 (m, 4H), 7.43 (t, J = 1.8 Hz, 1H), 7.39 (d, J = 8.4 Hz, 1H),
    6.28 (bs, 1H), 4.27 (t, J = 5.1 Hz, 2H), 4.08 (d, J = 17.2 Hz, 1H),
    3.65-3.75 (m, 3H), 2.44 (s, 3H), 2.08 (s, 3H).
    5-080 (B) δ 7.45-7.55 (m, 4H), 7.35-7.45 (m, 2H), 6.48 (bs, 1H), 4.80 (bs, 1H),
    4.28 (t, J = 5.0 Hz, 2H), 4.08 (d, J = 17.2 Hz, 1H), 3.70 (d, J = 17.2 Hz, 1H),
    3.65-3.7 (m, 2H), 3.15-3.25 (m, 2H), 2.46 (s, 3H), 1.13 (t, J = 7.2 Hz, 3H).
    5-083 (A) δ 7.4-7.55 (m, 6H), 5.95 (bs, 1H), 4.48 (t, J = 5.4 Hz, 1H),
    4.05 (d, J = 17.4 Hz, 1H), 3.66 (d, J = 17.4 Hz, 1H), 3.59 (t, J = 5.4 Hz, 2H),
    3.44 (s, 6H), 2.48 (5, 3H).
    5-084 (A) δ 7.4-7.55 (m, 6H), 6.02 (bs, 1H), 4.63 (t, J = 5.1 Hz, 1H),
    4.08 (d, J = 16.8 Hz, 1H), 3.5-3.8 (m, 7H), 2.48 (s, 3H),
    1.22 (t, J = 6.6 Hz, 6H).
    5-085 (B) δ 7.45-7.55 (m, 4H), 7.43 (t, J = 1.8 Hz, 1H), 7.39 (d, J = 8.4 Hz, 1H),
    6.31 (d, J = 8.1 Hz, 1H), 4.81 (bs, 1H), 4.35-4.45 (m, 1H),
    4.22 (dd, J = 11.5, 6.8 Hz, 1H), 4.10 (dd, J = 11.5, 3.7 Hz, 1H),
    4.08 (d, J = 17.2 Hz, 1H), 3.70 (d, J = 17.2 Hz, 1H), 3.15-3.25 (m, 2H),
    2.45 (s, 3H), 1.27 (d, J = 7.1 Hz, 3H), 1.13 (t, J = 7.2 Hz, 3H).
    5-086 (A) δ 7.35-7.6 (m, 6H), 6.24 (bs, 1H), 4.0-4.15 (m, 2H), 3.65-3.9 (m, 4H),
    3.25-3.35 (m, 1H), 2.46 (s, 3H), 1.85-2.1 (m, 3H), 1.55-1.7 (m, 1H).
    5-087 (A) δ 7.35-7.55 (m, 6H), 5.97 (bs, 1H), 4.08 (d, J = 17.4 Hz, 1H),
    3.55-4.0 (m, 4H), 3.69 (d, J = 17.1 Hz, 1H), 3.45-3.5 (m, 2H),
    2.55-2.65 (m, 1H), 2.47 (s, 3H), 2.05-2.15 (m, 1H), 1.6-1.75 (m, 1H).
    5-090 (A) δ 7.4-7.55 (m, 6H), 6.14 (bs, 1H), 4.75 (t, J = 4.5 Hz, 1H),
    4.1-4.2 (m, 2H), 4.08 (d, J = 17.4 Hz, 1H), 3.75-3.9 (m, 2H),
    3.71 (d, J = 17.4 Hz, 1H), 3.5-3.65 (m, 2H), 2.47 (s, 3H), 2.0-2.15 (m, 1H),
    1.3-1.45 (m, 1H).
    5-092 (A) δ 7.35-7.6 (m, 6H), 7.05 (bs, 1H), 4.08 (d, J = 17.1 Hz, 1H),
    3.9-4.05 (m, 2H), 3.70 (d, J = 17.1 Hz, 1H), 3.1-3.25 (m, 1H),
    2.8-2.95 (m, 1H), 2.66 (s, 3H), 2.47 (s, 3H).
    5-094 (A) δ 7.4-7.6 (m, 6H), 6.73 (bs, 1H), 4.08 (d, J = 17.1 Hz, 1H),
    3.9-4.05 (m, 2H), 3.70 (d, J = 17.1 Hz, 1H), 3.28 (t, J = 5.7 Hz, 2H),
    3.08 (q, J = 7.5 Hz, 2H), 2.47 (s, 3H), 1.43 (t, J = 7.5 Hz, 3H).
    5-095 (A) δ 7.2-7.6 (m, 11H), 6.09 (bs, 1H), 4.08 (d, J = 17.1 Hz, 1H),
    3.75 (s, 2H), 3.70 (d, J = 17.1 Hz, 1H), 3.5-3.6 (m, 2H),
    2.68 (t, J = 6.3 Hz, 2H), 2.45 (s, 3H).
    5-096 (A) δ 7.35-7.55 (m, 11H), 6.62 (t, J = 6.0 Hz, 1H), 4.30 (s, 2H),
    4.07 (d, J = 17.4 Hz, 1H), 3.85-3.95 (m, 2H), 3.69 (d, J = 17.4 Hz, 1H),
    3.1-3.2 (m, 2H), 2.41 (s, 3H).
    5-097 (A) δ 7.35-7.55 (m, 6H), 7.32 (s, 1H), 6.30 (bs, 1H),
    6.22 (d, J = 2.7 Hz, 1H), 6.13 (bs, 1H), 4.08 (d, J = 17.4 Hz, 1H),
    3.77 (s, 2H), 3.70 (d, J = 17.4 Hz, 1H), 3.55-3.65 (m, 2H),
    2.78 (t, J = 6.3 Hz, 2H), 2.47 (s, 3H).
    5-098 (A) δ 7.4-7.55 (m, 7H), 6.55-6.6 (m, 2H), 6.45 (dd, J = 3.0, 1.8 Hz, 1H),
    4.39 (s, 2H), 4.07 (d, J = 17.4 Hz, 1H), 3.85-3.95 (m, 2H),
    3.69 (d, J = 17.4 Hz, 1H), 3.25-3.3 (m, 2H), 2.45 (s, 3H).
    5-099 (A) δ 7.4-7.6 (m, 6H), 6.22 (t, J = 5.4 Hz, 1H), 4.08 (d, J = 17.0 Hz, 1H),
    3.6-3.75 (m, 2H), 3.35-3.5 (m, 1H), 2.85-3.05 (m, 1H), 2.49 (s, 3H),
    2.11 (s, 3H), 1.35 (d, J = 6.9 Hz, 3H).
    5-100 (A) δ 7.4-7.6 (m, 6H), 7.15-7.25 and 6.9-7.0 (m, 1H), 3.9-4.2 (m, 2H),
    3.6-3.85 (m, 2H), 2.85-3.2 (m, 1H), 2.68 and 2.56 (s, 3H), 2.49 (s, 3H),
    1.32 (d, J = 6.9 Hz, 3H).
    5-101 (A) δ 7.4-7.6 (m, 6H), 6.65 (t, J = 5.8 Hz, 1H), 4.08 (d, J = 17.3 Hz, 1H),
    3.75-4.0 (m, 2H), 3.69 (d, J = 17.3 Hz, 1H), 3.25-3.45 (m, 1H),
    2.94 (s, 3H), 2.49 (s, 3H), 1.50 (d, J = 6.9 Hz, 3H).
    5-102 (A) δ 7.35-7.65 (m, 6H), 6.08 (bs, 1H), 4.3-4.45 (m, 1H),
    4.09 (d, J = 17.4 Hz, 1H), 3.71 (d, J = 17.4 Hz, 1H), 2.71 (d, J = 5.7 Hz, 2H),
    2.44 (s, 3H), 2.17 (s, 3H), 1.34 (d, J = 6.6 Hz, 3H).
    5-103 (A) δ 7.4-7.6 (m, 6H), 6.46 (d, J = 8.1 Hz, 1H), 4.6-4.75 (m, 1H),
    4.08 (d, J = 17.1 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H),
    3.42 (dd, J = 14.4, 6.3 Hz, 1H), 3.26 (dd, J = 14.4, 5.1 Hz, 1H), 3.03 (s, 3H),
    2.45 (s, 3H), 1.53 (d, J = 6.9 Hz, 3H).
    5-104 (A) δ 7.45-7.55 (m, 4H), 7.4-7.45 (m, 2H), 5.75 (bs, 1H),
    4.07 (d, J = 17.4 Hz, 1H), 3.69 (d, J = 17.4 Hz, 1H), 3.07 (s, 2H),
    2.48 (s, 3H), 2.18 (s, 3H), 1.51 (s, 6H).
    5-112 (A) δ 7.45-7.65 (m, 6H), 7.43 and 6.93 (t, J = 4.8 Hz, 1H), 6.29 (bs, 1H),
    4.33 and 4.25 (t, J = 4.7 Hz, 2H), 4.08 (d, J = 17.1 Hz, 1H),
    3.70 (d, J = 17.4 Hz, 1H), 2.48 (s, 3H).
    5-114 (A) δ 7.4-7.6 (m, 6H), 7.43 and 6.85 (bs, 1H), 6.30 (bs, 1H),
    4.25-4.35 and 4.2-4.25 (m, 2H), 4.08 (d, J = 17.4 Hz, 1H),
    3.93 and 3.86 (d, J = 7.2 Hz, 2H), 3.70 (d, J = 17.4 Hz, 1H), 2.49 (s, 3H),
    1.1-1.3 (m, 1H), 0.5-0.6 (m, 2H), 0.2-0.3 (m, 2H).
    5-115 (A) δ 7.57 and 6.86 (t, J = 4.4 Hz, 1H), 7.25-7.55 (m, 10H), 6.26 (bs, 1H),
    5.10 and 5.02 (s, 2H), 4.28 and 4.20 (t, J = 5.3 Hz, 2H),
    4.08 (d, J = 17.1 Hz, 1H), 3.70 (d, J = 17.1 Hz, 1H), 2.44 (s, 3H).
    5-116 (A) δ 7.4-7.5 (m, 6H), 7.39 and 6.79 (t, J = 4.5 Hz, 1H),
    6.25 and 6.15 (bs, 1H), 4.0-4.3 (m, 4H), 4.05 (d, J = 17.4 Hz, 1H),
    3.67 (d, J = 17.4 Hz, 1H), 2.46 and 2.45 (s, 3H), 0.9-1.25 (m, 2H),
    0.01 (s, 9H).
    5-118 (A) δ 7.45-7.55 (m, 4H), 7.35-7.45 (m, 2H), 6.19 (bs, 1H),
    4.7-4.85 (m, 1H), 4.08 (d, J = 17.4 Hz, 1H), 3.7-3.8 (m, 1H),
    3.70 (d, J = 17.4 Hz, 1H), 3.5-3.6 (m, 1H), 3.0-3.15 (m, 1H),
    2.7-2.85 (m, 1H), 2.47 (s, 3H), 2.00 (s, 3H).
    5-120 (A) δ 7.4-7.6 (m, 6H), 7.11 (d, J = 9.6 Hz, 1H), 6.30 (d, J = 9.6 Hz, 1H),
    4.0-4.25 (m, 3H), 3.70 (d, J = 17.0 Hz, 1H), 2.50 (s, 3H).
    5-122 (A) δ 7.4-7.6 (m, 7H), 6.61 (d, J = 3.3 Hz, 1H), 6.49 (d, J = 8.4 Hz, 1H),
    6.44 (dd, J = 3.3, 2.1 Hz, 1H), 6.33 (d, J = 8.4 Hz, 1H),
    4.08 (d, J = 17.3 Hz, 1H), 3.70 (d, J = 17.3 Hz, 1H), 2.48 (s, 3H).
    5-123 (A) δ 7.3-7.6 (m, 8H), 7.0-7.1 (m, 1H), 6.49 (d, J = 8.8 Hz, 1H),
    6.42 (d, J = 8.8 Hz, 1H), 4.08 (d, J = 17.0 Hz, 1H), 3.69 (d, J = 17.0 Hz, 1H),
    2.50 (s, 3H).
    5-126 (A) δ 8.62 (d, J = 5.0 Hz, 1H), 7.85 (td, J = 8.1, 2.1 Hz, 1H),
    7.35-7.65 (m, 9H), 6.15 (d, J = 6.9 Hz, 1H), 4.09 (d, J = 17.0 Hz, 1H),
    3.71 (d, J = 17.0 Hz, 1H), 2.52 (s, 3H).
    5-128 (A) δ 7.45-7.65 (m, 6H), 6.33 (bs, 1H), 4.23 (d, J = 5.1 Hz, 2H),
    4.09 (d, J = 17.4 Hz, 1H), 3.81 (s, 3H), 3.70 (d, J = 17.4 Hz, 1H),
    2.49 (s, 3H).
    5-130 (B) δ 7.4-7.55 (m, 6H), 6.33 (d, J = 6.6 Hz, 1H), 4.75-4.85 (m, 1H),
    4.08 (d, J = 17.2 Hz, 1H), 3.81 (s, 3H), 3.70 (d, J = 17.2 Hz, 1H),
    2.49 (s, 3H), 1.55 (s, 3H).
    5-131 (B) δ 7.4-7.55 (m, 6H), 6.34 (d, J = 7.6 Hz, 1H), 4.7-4.8 (m, 1H),
    4.2-4.3 (m, 2H), 4.08 (d, J = 17.4 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H),
    2.49 (s, 3H), 1.54 (t, J = 7.0 Hz, 3H), 1.32 (t, J = 7.2 Hz, 3H).
    5-132 (A) δ 7.4-7.55 (m, 6H), 6.36 (bs, 1H), 4.75-4.9 (m, 1H), 4.6-4.75 (m, 1H),
    4.4-4.55 (m, 1H), 4.18 (d, J = 17.4 Hz, 1H), 3.71 (d, J = 17.4 Hz, 1H),
    2.45 (s, 3H), 1.57 (d, J = 7.2 Hz, 3H).
    5-133 (A) δ 7.4-7.6 (m, 6H), 7.06 (d, J = 6.6 Hz, 1H), 5.76 (t, J = 6.6 Hz, 1H),
    4.27 (d, J = 6.6 Hz, 1H), 4.08 (d, J = 17.1 Hz, 1H), 3.89 (s, 3H),
    3.70 (d, J = 17.1 Hz, 1H), 2.49 (s, 3H).
    5-134 (A) δ 7.4-7.6 (m, 6H), 6.79 (d, J = 9.4 Hz, 1H), 5.72 (d, J = 9.4 Hz, 1H),
    4.09 (d, J = 17.3 Hz, 1H), 3.87 (s, 3H), 3.71 (d, J = 17.3 Hz, 1H),
    3.59 (s, 3H), 2.51 (s, 3H).
    5-136 (A) δ 7.35-7.55 (m, 6H), 6.44 (bs, 1H), 4.05-4.25 (m, 3H),
    3.6-3.8 (m, 3H), 2.66 (t, J = 6.0 Hz, 2H), 2.46 (s, 3H),
    1.27 (t, J = 7.2 Hz, 3H).
    5-138 (A) δ 7.45-7.6 (m, 6H), 7.09 (bs, 1H), 6.69 (bs, 1H), 4.05-4.15 (m, 3H),
    3.72 (d, J = 17.4 Hz, 1H), 2.83 (d, J = 4.8 Hz, 3H), 2.44 (s, 3H).
    5-139 (A) δ 7.5-7.6 (m, 5H), 7.43 (s, 1H), 6.98 (bs, 1H), 4.23 (d, J = 3.9 Hz, 2H),
    4.09 (d, J = 17.1 Hz, 1H), 3.71 (d, J = 17.1 Hz, 1H), 3.04 (s, 3H),
    3.02 (s, 3H), 2.50 (s, 3H).
    5-141 (B) δ 7.4-7.55 (m, 6H), 7.05-7.1 (m, 1H), 6.62 (bs, 1H),
    4.05-4.15 (m, 3H), 3.72 (d, J = 17.2 Hz, 1H), 3.23 (dd, J = 13.8, 7.2 Hz, 2H),
    2.45 (s, 3H), 1.5-1.6 (m, 2H), 0.91 (t, J = 7.4 Hz, 3H).
    5-143 (B) δ 7.4-7.55 (m, 6H), 6.9-7.05 (m, 1H), 6.45-6.55 (m, 1H),
    4.05-4.2 (m, 3H), 3.70 (d, J = 17.2 Hz, 1H), 3.1-3.15 (m, 2H),
    2.45-2.5 (m, 4H), 0.9-1.0 (m, 6H).
    5-145 (B) δ 7.4-7.55 (m, 6H), 6.78 (bs, 1H), 5.93 (bs, 1H), 4.0-4.15 (m, 3H),
    3.70 (d, J = 16.8 Hz, 1H), 2.48 (s, 3H), 1.38 (s, 9H).
    5-146 (B) δ 7.4-7.55 (m, 6H), 7.01 (bs, 1H), 6.53 (bs, 1H), 4.05-4.2 (m, 3H),
    3.71 (d, J = 17.4 Hz, 1H), 3.05-3.1 (m, 2H), 2.46 (s, 3H), 0.91 (s, 9H).
    5-147 (B) δ 7.4-7.55 (m, 6H), 6.89 (bs, 2H), 4.56 (t, J = 5.0 Hz, 1H),
    4.44 (t, J = 5.0 Hz, 1H), 4.16 (d, J = 5.0 Hz, 2H), 4.19 (d, J = 17.2 Hz, 1H),
    3.71 (d, J = 17.2 Hz, 1H), 3.5-3.7 (m, 2H), 2.46 (s, 3H).
    5-149 (A) δ 7.45-7.6 (m, 5H), 7.42 (s, 1H), 7.27 (bs, 1H), 4.25-4.4 (m, 2H),
    4.09 (d, J = 17.4 Hz, 1H), 3.6-3.8 (m, 5H), 3.17 (s, 3H), 2.49 (s, 3H).
    5-150 (B) δ 7.4-7.55 (m, 6H), 6.8-7.2 (m, 2H), 4.16 (d, J = 5.0 Hz, 2H),
    4.09 (d, J = 17.2 Hz, 1H), 3.5-3.75 (m, 3H), 3.48 (t, J = 5.8 Hz, 2H),
    2.48 (s, 3H).
    5-152 (A) δ 7.4-7.55 (m, 6H), 7.05 (bs, 1H), 6.90 (bs, 1H), 4.0-4.2 (m, 3H),
    3.71 (d, J = 17.0 Hz, 1H), 3.5-3.6 (m, 2H), 3.4-3.5 (m, 2H), 2.45 (s, 3H),
    1.9-2.1 (m, 2H).
    5-153 (B) δ 7.4-7.55 (m, 6H), 6.7-7.05 (m, 2H), 4.15-4.2 (m, 2H),
    4.09 (d, J = 17.2 Hz, 1H), 3.75-3.9 (m, 1H), 3.71 (d, J = 17.2 Hz, 1H),
    3.05-3.2 (m, 1H), 2.47 (s, 3H), 1.49 (bs, 1H), 1.6-1.7 (m, 1H),
    1.2-1.3 (m, 1H).
    5-154 (A) δ 7.45-7.55 (m, 5H), 7.43 (s, 1H), 6.86 (bs, 1H), 6.77 (bs, 1H),
    4.05-4.15 (m, 3H), 3.65-3.8 (m, 3H), 3.45-3.55 (m, 2H), 2.46 (s, 3H),
    1.69 (bs, 1H).
    5-155 (B) δ 7.5-7.55 (m, 5H), 7.43 (t, J = 1.8 Hz, 1H), 6.9-7.0 (m, 1H),
    4.25-4.4 (m, 2H), 4.19 (d, J = 17.4 Hz, 1H), 3.8-3.9 (m, 2H),
    3.70 (d, J = 17.4 Hz, 1H), 3.63 (t, J = 5.2 Hz, 1H), 3.49 (t, J = 5.2 Hz, 1H),
    3.13 and 3.04 (s, 3H), 2.50 (s, 3H).
    5-159 (B) δ 7.4-7.55 (m, 6H), 7.25-7.35 (m, 1H), 7.0-7.05 (m, 1H),
    4.10 (d, J = 17.2 Hz, 1H), 4.06 (bs, 2H), 3.77 (bs, 2H),
    3.73 (d, J = 17.2 Hz, 1H), 3.25 (t, J = 5.6 Hz, 2H), 2.96 (s, 3H),
    2.42 (s, 3H).
    5-161 (B) δ 7.4-7.55 (m, 6H), 6.96 (bs, 1H), 5.7-5.85 (m, 1H),
    5.15-5.35 (m, 2H), 4.2-4.3 (m, 2H), 4.05-4.15 (m, 2H), 3.92 (bs, 1H),
    3.71 (d, J = 17.2 Hz, 1H), 3.01 and 2.99 (s, 3H), 2.50 (s, 3H).
    5-162 (B) δ 7.45-7.55 (m, 5H), 7.4-7.45 (m, 1H), 6.97 (bs, 1H),
    5.7-5.85 (m, 2H), 5.15-5.3 (m, 4H), 4.27 (d, J = 4.0 Hz, 2H),
    4.10 (d, J = 17.2 Hz, 1H), 4.05 (d, J = 5.8 Hz, 2H), 3.91 (d, J = 5.8 Hz, 2H),
    3.72 (d, J = 17.2 Hz, 1H), 2.50 (s, 3H).
    5-163 (A) δ 7.4-7.6 (m, 6H), 6.9-7.2 (m, 2H), 5.38 (s, 1H), 5.30 (s, 1H),
    4.0-4.3 (m, 5H), 3.70 (d, J = 17.0 Hz, 1H), 2.44 (s, 3H).
    5-165 (B) δ 7.4-7.55 (m, 6H), 7.00 (bs, 2H), 4.05-4.2 (m, 5H),
    3.72 (d, J = 17.2 Hz, 1H), 2.54 (s, 3H), 2.22 (s, 1H).
    5-167 (B) δ 8.78 (d, J = 1.8 Hz, 1H), 7.45-7.55 (m, 6H), 7.43 (t, J = 1.8 Hz, 1H),
    6.65-6.8 (m, 2H), 4.65 (d, J = 7.4 Hz, 2H), 4.05-4.2 (m, 3H),
    3.70 (d, J = 17.2 Hz, 1H), 2.46 (s, 3H).
    5-168 (B) δ 8.52 (d, J = 4.1 Hz, 1H), 7.67 (td, J = 7.8, 1.8 Hz, 1H),
    7.4-7.55 (m, 8H), 7.2-7.25 (m, 1H), 6.83 (bs, 1H), 4.59 (d, J = 5.0 Hz, 2H),
    4.22 (d, J = 5.0 Hz, 2H), 4.08 (d, J = 17.2 Hz, 1H), 3.70 (d, J = 17.2 Hz, 1H),
    2.47 (s, 3H).
    5-171 (B) δ 7.45-7.55 (m, 6H), 6.94 (bs, 1H), 4.25 (d, J = 3.8 Hz, 2H),
    4.08 (d, J = 17.2 Hz, 1H), 3.65-3.75 (m, 7H), 3.48 (t, J = 4.4 Hz, 2H),
    2.50 (s, 3H).
    5-173 (B) δ 7.2-7.6 (m, 7H), 6.6-7.1 (m, 6H), 4.0-4.6 (m, 3H),
    3.70 (d, J = 17.0 Hz, 1H), 3.33 (s, 3H), 2.49 (s, 3H).
    5-176 (B) δ 7.3-7.55 (m, 12H), 6.37 (bs, 1H), 5.71 (d, J = 7.0 Hz, 1H),
    4.08 (d, J = 17.2 Hz, 1H), 3.71 (d, J = 17.2 Hz, 1H), 2.75 (d, J = 4.9 Hz, 3H),
    2.41 (s, 3H).
    5-178 (A) δ 7.45-7.6 (m, 5H), 7.43 (s, 1H), 6.62 (bs, 1H),
    4.37 (t, J = 9.3 Hz, 2H), 4.23 (d, J = 4.5 Hz, 2H), 4.09 (d, J = 17.1 Hz, 1H),
    3.86 (t, J = 9.3 Hz, 2H), 3.71 (d, J = 17.1 Hz, 1H), 2.48 (s, 3H).
    5-179 (A) δ 8.10 (bs, 1H), 7.4-7.65 (m, 7H), 7.06 (bs, 1H),
    4.43 (d, J = 5.1 Hz, 2H), 4.09 (d, J = 17.1 Hz, 1H), 3.71 (d, J = 17.1 Hz, 1H),
    2.49 (s, 3H).
    5-180 (A) δ 7.65-7.8 (m, 2H), 7.1-7.6 (m, 12H), 6.03 (d, J = 7.4 Hz, 1H),
    4.08 (d, J = 17.0 Hz, 1H), 3.70 (d, J = 17.0 Hz, 1H), 2.45 (s, 3H).
    5-181 (A) δ 7.51 (bs, 4H), 7.4-7.45 (m, 1H), 7.38 (d, J = 8.5 Hz, 1H),
    5.5-5.6 (m, 1H), 4.08 (d, J = 17.1 Hz, 1H), 3.69 (d, J = 17.1 Hz, 1H),
    2.97 (d, J = 6.1 Hz, 2H), 2.46 (s, 3H), 0.13 (s, 9H).
    5-182 (A) δ 7.51 (bs, 4H), 7.4-7.45 (m, 2H), 5.85-6.05 (m, 1H), 5.81 (bs, 1H),
    5.15-5.35 (m, 2H), 4.05-4.15 (m, 3H), 3.69 (d, J = 17.4 Hz, 1H),
    2.49 (s, 3H).
    5-183 (A) δ 7.4-7.75 (m, 5H), 7.33 (d, J = 7.8 Hz, 1H), 4.04 (d, J = 17.1 Hz, 1H),
    3.75 (m, 1H), 3.66 (d, J = 17.4 Hz, 1H), 3.37 (m, 1H), 3.08 (m, 2H),
    1.25 (t, J = 7.4 Hz, 3H), 1.04 (t, J = 7.2 Hz, 3H).
    5-184 (A) δ 7.51 (bs, 4H), 7.4-7.5 (m, 2H), 6.10 (t, J = 6.9 Hz, 1H),
    5.95 (bs, 1H), 4.17 (t, J = 6.6 Hz, 2H), 4.08 (d, J = 17.1 Hz, 1H),
    3.69 (d, J = 17.4 Hz, 1H), 2.48 (s, 3H).
    5-185 (A) δ 7.4-7.55 (m, 6H), 6.58 and 6.34 (s, 1H), 6.10 and 5.99 (bs, 1H),
    4.49 and 4.30 (d, J = 6.0 Hz, 2H), 4.08 (d, J = 17.1 Hz, 1H),
    3.69 (d, J = 17.1 Hz, 1H), 2.50 and 2.48 (s, 3H).
    5-186 (A) δ 7.35-7.55 (m, 6H), 6.03 (bs, 1H), 4.27 (q, J = 2.4 Hz, 2H),
    4.08 (d, J = 17.4 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H), 2.47 (s, 3H),
    2.30 (t, J = 2.4 Hz, 1H).
    5-189 (A) δ 7.25-7.55 (m, 11H), 6.0-6.2 (m, 1H), 5.2-5.4 (m, 1H),
    4.06 (d, J = 17.3 Hz, 1H), 3.68 (d, J = 17.3 Hz, 1H), 2.41 (s, 3H),
    1.60 (d, J = 6.9 Hz, 3H).
    5-191 (A) δ 7.2-7.6 (m, 11H), 6.09 (bs, 1H), 5.06 (q, J = 7.5 Hz, 1H),
    4.06 (d, J = 17.1 Hz, 1H), 3.68 (d, J = 17.1 Hz, 1H), 2.40 (s, 3H),
    1.85-2.0 (m, 2H), 0.97 (t, J = 7.2 Hz, 3H).
    5-194 (B) δ 7.3-7.6 (m, 11H), 6.42 (d, J = 9.6 Hz, 1H), 6.26 (d, J = 9.6 Hz, 1H),
    4.07 (d, J = 17.2 Hz, 1H), 3.85-3.95 (m, 1H), 3.7-3.8 (m, 1H),
    3.69 (d, J = 17.2 Hz, 1H), 2.50 (s, 3H), 1.33 (t, J = 7.2 Hz, 3H).
    5-205 (A) δ 7.35-7.55 (m, 7H), 6.25-6.35 (m, 2H), 6.10 (bs, 1H),
    4.62 (d, J = 5.4 Hz, 2H), 4.07 (d, J = 17.1 Hz, 1H), 3.69 (d, J = 17.1 Hz, 1H),
    2.46 (s, 3H).
    5-207 (A) δ 7.3-7.55 (m, 6H), 6.7-6.8 (m, 2H), 6.39 (bs, 1H),
    4.64 (d, J = 6.0 Hz, 2H), 4.07 (d, J = 17.4 Hz, 1H), 3.69 (d, J = 17.4 Hz, 1H),
    2.43 (s, 3H).
    5-208 (A) δ 7.4-7.6 (m, 6H), 6.37 (bs, 1H), 6.04 (s, 1H), 4.66 (d, J = 5.7 Hz, 2H),
    4.08 (d, J = 17.4 Hz, 1H), 3.69 (d, J = 17.4 Hz, 1H), 2.49 (s, 3H),
    2.43 (s, 3H).
    5-209 (A) δ 7.35-7.6 (m, 6H), 6.57 (t, J = 6.0 Hz, 1H), 6.31 (s, 1H),
    4.70 (d, J = 6.0 Hz, 2H), 4.09 (d, J = 17.4 Hz, 1H), 3.71 (d, J = 17.4 Hz, 1H),
    2.43 (s, 3H).
    5-212 (A) δ 7.56 (s, 1H), 7.35-7.55 (m, 6H), 5.90 (bs, 1H),
    4.46 (d, J = 5.4 Hz, 2H), 4.07 (d, J = 17.1 Hz, 1H), 3.85 (s, 3H),
    3.68 (d, J = 17.1 Hz, 1H), 2.47 (s, 3H).
    5-213 (A) δ 7.3-7.55 (m, 6H), 6.19 (bs, 1H), 4.43 (d, J = 5.4 Hz, 2H),
    4.07 (d, J = 17.4 Hz, 1H), 3.78 (s, 3H), 3.72 (d, J = 17.1 Hz, 1H),
    2.43 (s, 3H).
    5-216 (A) δ 7.74 (d, J = 3.3 Hz, 1H), 7.45-7.55 (m, 5H), 7.43 (bs, 1H),
    7.40 (d, J = 3.3 Hz, 1H), 6.66 (bs, 1H), 4.95 (d, J = 5.4 Hz, 2H),
    4.08 (d, J = 16.8 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H), 2.50 (s, 3H).
    5-217 (A) δ 7.75 (d, J = 3.3 Hz, 1H), 7.3-7.6 (m, 13H), 6.59 (d, J = 7.4 Hz, 1H),
    4.08 (d, J = 17.3 Hz, 1H), 3.69 (d, J = 17.3 Hz, 1H), 2.46 (s, 3H).
    5-218 (A) δ 7.76 (s, 1H), 7.4-7.75 (m, 6H), 6.78 (bs, 1H),
    4.93 (d, J = 3.6 Hz, 2H), 4.09 (d, J = 17.4 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H),
    2.47 (s, 3H).
    5-220 (A) δ 7.4-7.55 (m, 6H), 7.17 (s, 1H), 6.40 (bs, 1H),
    4.64 (d, J = 5.7 Hz, 2H), 4.08 (d, J = 17.1 Hz, 1H), 3.73 (d, J = 17.1 Hz, 1H),
    2.46 (s, 3H).
    5-221 (A) δ 7.4-7.55 (m, 6H), 7.07 (s, 1H), 6.42 (bs, 1H),
    4.66 (d, J = 5.4 Hz, 2H), 4.05 (d, J = 17.4 Hz, 1H), 3.66 (d, J = 17.4 Hz, 1H),
    2.70 (s, 3H), 2.47 (s, 3H).
    5-222 (A) δ 8.76 (s, 1H), 7.81 (s, 1H), 7.50 (bs, 4H), 7.35-7.45 (m, 2H),
    6.36 (bs, 1H), 4.83 (d, J = 6.0 Hz, 2H), 4.07 (d, J = 17.4 Hz, 1H),
    3.69 (d, J = 17.1 Hz, 1H), 2.46 (s, 3H).
    5-223 (A) δ 7.45-7.55 (m, 4H), 7.35-7.45 (m, 3H), 6.27 (t, J = 6.0 Hz, 1H),
    4.71 (d, J = 6.0 Hz, 2H), 4.08 (d, J = 17.4 Hz, 1H), 3.69 (d, J = 17.4 Hz, 1H),
    2.48 (s, 3H).
    5-224 (B) δ 7.91 (bs, 1H), 7.4-7.55 (m, 6H), 6.84 (s, 1H), 6.79 (s, 1H),
    4.66 (d, J = 4.9 Hz, 2H), 4.07 (d, J = 17.0 Hz, 1H), 3.80 (s, 3H),
    3.77 (d, J = 17.0 Hz, 1H), 2.45 (s, 3H).
    5-225 (B) δ 7.25-7.55 (m, 7H), 6.9-7.0 (m, 1H), 6.84 (s, 1H),
    4.57 (d, J = 5.5 Hz, 2H), 4.07 (d, J = 17.0 Hz, 1H), 3.70 (d, J = 17.0 Hz, 1H),
    3.63 (s, 3H), 2.42 (s, 3H).
    5-226 (B) δ 8.62 (s, 1H), 7.35-7.65 (m, 6H), 6.8-6.9 (m, 1H),
    5.07 (d, J = 6.1 Hz, 2H), 4.06 (d, J = 17.0 Hz, 1H), 3.69 (d, J = 17.0 Hz, 1H),
    2.42 (s, 3H).
    5-227 (B) δ 7.45-7.55 (m, 5H), 7.35-7.4 (m, 1H), 6.9-6.95 (m, 1H),
    4.80 (d, J = 5.8 Hz, 2H), 4.08 (d, J = 17.0 Hz, 1H), 3.71 (d, J = 17.0 Hz, 1H),
    2.68 (s, 3H), 2.41 (s, 3H).
    5-230 (A) δ 8.43 (s, 1H), 7.45-7.55 (m, 5H), 7.43 (s, 1H),
    6.68 (t, J = 5.7 Hz, 1H), 4.90 (d, J = 5.7 Hz, 2H), 4.09 (d, J = 17.1 Hz, 1H),
    3.71 (d, J = 17.1 Hz, 1H), 2.48 (s, 3H).
    5-231 (A) δ 7.45-7.55 (m, 5H), 7.43 (s, 1H), 6.78 (t, J = 5.7 Hz, 1H),
    4.80 (d, J = 5.7 Hz, 2H), 4.09 (d, J = 17.1 Hz, 1H), 3.72 (d, J = 17.1 Hz, 1H),
    2.54 (s, 3H), 2.47 (s, 3H).
    5-232 (A) δ 9.14 (s, 1H), 7.45-7.55 (m, 6H), 6.85 (t, J = 5.7 Hz, 1H),
    5.09 (d, J = 5.7 Hz, 2H), 4.08 (d, J = 17.4 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H),
    2.48 (s, 3H).
    5-233 (B) δ 8.42 (s, 1H), 8.05-8.15 (m, 1H), 7.87 (s, 1H), 7.35-7.55 (m, 6H),
    5.70 (d, J = 6.4 Hz, 2H), 4.08 (d, J = 17.0 Hz, 1H), 3.72 (d, J = 17.0 Hz, 1H),
    2.32 (s, 3H).
    5-235 (A) δ 8.52 (d, J = 4.8 Hz, 1H), 7.65-7.75 (m, 1H), 7.15-7.55 (m, 9H),
    5.32 (dq, J = 6.9 Hz, 1H), 4.09 (d, J = 16.8 Hz, 1H), 3.70 (d, J = 16.8 Hz, 1H),
    2.48 (s, 3H), 1.59 (d, J = 6.9 Hz, 3H).
    5-238 (B) δ 7.66 (t, J = 7.7 Hz, 1H), 7.45-7.55 (m, 5H), 7.43 (t, J = 1.8 Hz, 1H),
    7.25-7.35 (m, 2H), 7.02 (t, J = 5.3 Hz, 1H), 4.69 (d, J = 5.3 Hz, 2H),
    4.10 (d, J = 17.2 Hz, 1H), 3.72 (d, J = 17.4 Hz, 1H), 2.47 (s, 3H).
    5-239 (B) δ 8.2-8.3 (m, 1H), 7.55-7.65 (m, 2H), 7.45-7.55 (m, 3H),
    7.4-7.5 (m, 3H), 7.25-7.4 (m, 2H), 4.79 (d, J = 6.2 Hz, 2H),
    4.07 (d, J = 17.2 Hz, 1H), 3.69 (d, J = 17.2 Hz, 1H), 2.41 (s, 3H).
    5-240 (A) δ 8.58 (d, J = 1.8 Hz, 1H), 8.53 (dd, J = 4.8, 1.8 Hz, 1H),
    7.72 (d, J = 7.8 Hz, 1H), 7.4-7.55 (m, 6H), 7.30 (dd, J = 7.8, 4.8 Hz, 1H),
    6.40 (t, J = 6.0 Hz, 1H), 4.63 (d, J = 6.0 Hz, 2H), 4.08 (d, J = 17.4 Hz, 1H),
    3.70 (d, J = 17.4 Hz, 1H), 2.46 (s, 3H).
    5-242 (A) δ 8.57 (d, J = 6.0 Hz, 2H), 7.4-7.55 (m, 6H), 7.26 (d, J = 6.0 Hz, 2H),
    6.42 (t, J = 6.0 Hz, 1H), 4.64 (d, J = 6.0 Hz, 2H), 4.08 (d, J = 17.4 Hz, 1H),
    3.70 (d, J = 17.4 Hz, 1H), 2.48 (s, 3H).
    5-243 (A) δ 8.73 (d, J = 5.4 Hz, 2H), 7.5-7.6 (m, 5H), 7.43 (s, 1H),
    7.24 (t, J = 5.4 Hz, 1H), 7.19 (bs, 1H), 4.89 (d, J = 5.2 Hz, 2H),
    4.10 (d, J = 17.0 Hz, 1H), 3.72 (d, J = 17.0 Hz, 1H), 2.53 (s, 3H).
    5-245 (A) δ 9.18 (bs, 1H), 8.73 (d, J = 5.2 Hz, 1H), 7.56 (s, 3H), 7.52 (bs, 2H),
    7.4-7.45 (m, 1H), 7.35-7.4 (m, 1H), 7.04 (bs, 1H), 4.77 (d, J = 4.8 Hz, 2H),
    4.10 (d, J = 17.2 Hz, 1H), 3.72 (d, J = 17.2 Hz, 1H), 2.52 (s, 3H).
    5-246 (B) δ 8.69 (s, 1H), 8.53 (s, 2H), 7.5-7.55 (m, 5H), 7.4-7.45 (m, 1H),
    6.95-7.0 (m, 1H), 4.81 (d, J = 5.3 Hz, 2H), 4.09 (d, J = 17.0 Hz, 1H),
    3.71 (d, J = 17.0 Hz, 1H), 2.49 (s, 3H).
    5-247 (B) δ 8.55-8.6 (m, 1H), 8.35-8.4 (m, 1H), 7.4-7.55 (m, 6H),
    6.95-7.05 (m, 1H), 4.75-4.8 (m, 2H), 4.08 (d, J = 17.0 Hz, 1H),
    3.72 (d, J = 17.0 Hz, 1H), 2.57 (s, 3H), 2.46 (s, 3H).
    5-265 (B) δ 7.5-7.55 (m, 5H), 7.4-7.45 (m, 1H), 6.70 (bs, 1H),
    4.08 (d, J = 19.0 Hz, 1H), 3.70 (d, J = 19.0 Hz, 1H), 2.51 (s, 3H),
    1.51 (s, 9H).
    5-277 (C) δ 7.45-7.65 (m, 6H), 7.44 (s, 1H), 7.33 (d, J = 7.8 Hz, 1H),
    7.21 (t, J = 7.8 Hz, 1H), 7.00 (d, J = 7.8 Hz, 1H), 6.89 (t, J = 7.8 Hz, 1H),
    6.69 (s, 1H), 4.08 (d, J = 17.4 Hz, 1H), 3.61 (d, J = 17.4 Hz, 1H),
    2.53 (s, 3H).
    5-278 (C) δ 7.45-7.65 (m, 6H), 7.44 (s, 1H), 7.20 (t, J = 8.4 Hz, 1H),
    6.85-6.95 (m, 2H), 6.81 (d, J = 8.4 Hz, 1H), 6.33 (s, 1H),
    4.10 (d, J = 17.1 Hz, 1H), 3.71 (d, J = 17.1 Hz, 1H), 2.52 (s, 3H).
    5-279 (A) δ 7.95 (s, 1H), 7.35-7.55 (m, 6H), 7.17 (d, J = 8.4 Hz, 2H),
    6.79 (d, J = 8.4 Hz, 2H), 6.42 (bs, 1H), 4.09 (d, J = 17.4 Hz, 1H),
    3.71 (d, J = 17.4 Hz, 1H), 2.43 (s, 3H).
    5-280 (A) δ 7.4-7.65 (m, 10H), 6.98 (d, J = 8.4 Hz, 2H), 4.10 (d, J = 17.3 Hz, 1H),
    3.72 (d, J = 17.3 Hz, 1H), 2.52 (s, 3H).
    5-296 (A) δ 8.76 (bs, 1H), 8.12 (bs, 1H), 8.02 (d, J = 5.4 Hz, 1H),
    7.35-7.5 (m, 6H), 6.26 (d, J = 5.4 Hz, 1H), 4.10 (d, J = 17.4 Hz, 1H),
    3.73 (d, J = 17.4 Hz, 1H), 2.45 (s, 3H), 2.43 (s, 3H).
    5-299 (C) δ 10.15 (bs, 1H), 9.37 (bs, 1H), 8.40 (s, 1H), 7.5-7.6 (m, 5H),
    7.46 (s, 1H), 6.69 (s, 1H), 4.17 (d, J = 17.4 Hz, 1H),
    3.86 (d, J = 17.4 Hz, 1H), 2.59 (s, 3H).
    5-301 (A) δ 7.4-7.65 (m, 7H), 7.34 (d, J = 9.3 Hz, 1H), 7.01 (d, J = 9.3 Hz, 1H),
    4.10 (d, J = 17.4 Hz, 1H), 4.13 (d, J = 17.4 Hz, 1H), 3.71 (d, J = 17.4 Hz, 1H),
    2.52 (s, 3H).
    5-303 (B) δ 10.38 (bs, 1H), 7.2-8.65 (m, 11H), 4.05-4.2 (m, 1H),
    3.7-3.85 (m, 1H), 2.44 and 2.37 (s, 3H).
    5-311 (A) δ 7.3-7.75 (m, 6H), 6.52 (t, J = 6.3 Hz, 1H), 4.05-4.2 (m, 3H),
    3.77 (d, J = 17.4 Hz, 1H), 2.60 (s, 3H).
    5-312 (A) δ 7.25-7.65 (m, 6H), 6.54 (t, J = 6.3 Hz, 1H), 3.9-4.15 (m, 2H),
    4.10 (d, J = 17.7 Hz, 1H), 3.73 (d, J = 17.7 Hz, 1H), 2.74 (q, J = 7.2 Hz, 2H),
    1.19 (t, J = 7.2 Hz, 3H).
    5-313 (A) δ 8.50 (d, J = 4.8 Hz, 1H), 7.70 (t, J = 4.5 Hz, 1H), 7.5-7.6 (m, 3H),
    7.49 (bs, 2H), 7.42 (bs, 1H), 7.15-7.35 (m, 3H), 4.73 (d, J = 4.5 Hz, 2H),
    4.11 (d, J = 17.4 Hz, 1H), 3.73 (d, J = 17.4 Hz, 1H), 2.84 (q, J = 7.5 Hz, 2H),
    1.23 (t, J = 7.5 Hz, 3H).
    5-316 (B) δ 7.72 (bs, 3H), 7.51 (bs, 2H), 7.45 (t, J = 1.8 Hz, 1H),
    7.15-7.25 (m, 1H), 4.71 (d, J = 6.0 Hz, 2H), 4.15-4.2 (m, 3H),
    3.73 (d, J = 17.2 Hz, 1H), 3.34 (t, J = 6.0 Hz, 1H).
    5-318 (A) δ 8.30 (d, J = 8.4 Hz, 1H), 8.18 (bs, 1H), 7.51 (s, 2H), 7.48 (s, 1H),
    7.25-7.45 (m, 6H), 7.16 (d, J = 8.4 Hz, 1H), 4.68 (d, J = 5.7 Hz, 2H),
    4.11 (d, J = 17.4 Hz, 1H), 3.97 (s, 3H), 3.73 (d, J = 17.4 Hz, 1H).
    5-320 (B) δ 8.11 (d, J = 8.0 Hz, 1H), 7.70 (s, 1H), 7.64 (d, J = 8.0 Hz, 1H),
    7.51 (s, 2H), 7.45 (s, 1H), 6.86 (t, J = 6.0 Hz, 1H), 4.0-4.25 (m, 3H),
    3.71 (d, J = 17.6, 1H).
    5-322 (A) δ 8.14 (t, J = 7.8 Hz, 1H), 7.54 (d, J = 7.8 Hz, 1H), 7.50 (d, J = 7.8 Hz, 1H),
    7.34 (s, 1H), 7.31 (s, 1H), 7.23 (s, 1H),
    7.09 and 7.05 (t, J = 6.3 Hz, 1H), 4.18 (qd, J = 18.5, 6.3 Hz, 2H),
    4.08 (d, J = 17.4 Hz, 1H), 3.74 (d, J = 17.4 Hz, 1H), 2.52 (s, 3H).
    5-325 (A) δ 8.59 (bs, 1H), 8.32 (s, 1H), 8.11 (bs, 1H), 8.03 (d, J = 8.1 Hz, 1H),
    7.85 (d, J = 8.1 Hz, 1H), 7.73 (t, J = 8.1 Hz, 1H), 7.51 (bs, 2H),
    7.43 (bs, 1H), 7.2-7.4 (m, 2H), 4.73 (bs, 2H),
    4.23 and 4.21 (d, J = 17.4 Hz, 1H), 3.86 and 3.85 (d, J = 17.4 Hz, 1H),
    2.96 and 2.93 (s, 3H).
    5-328 (A) δ 8.16 (t, J = 8.0 Hz, 1H), 7.6-7.8 (m, 3H), 7.56 (d, J = 8.0 Hz, 1H),
    7.52 (d, J = 8.1 Hz, 1H), 7.08 and 7.03 (t, J = 6.5 Hz, 1H), 4.35-4.55 (m, 2H),
    4.05-4.25 (m, 2H), 4.14 (d, J = 17.4 Hz, 1H), 3.79 (d, J = 17.4 Hz, 1H).
    5-330 (B) δ 8.57 (d, J = 4.8 Hz, 1H), 7.71 (td, J = 7.7, 1.8 Hz, 1H),
    7.62 (t, J = 4.6 Hz, 1H), 7.54 (d, J = 8.6 Hz, 1H), 7.50 (d, J = 1.6 Hz, 2H),
    7.42 (t, J = 1.8 Hz, 1H), 7.33 (d, J = 7.9 Hz, 1H),
    7.24 (dd, J = 7.5, 5.0 Hz, 1H), 6.9-7.0 (m, 2H), 5.73 (bs, 2H),
    4.72 (d, J = 4.8 Hz, 2H), 4.04 (d, J = 17.2 Hz, 1H), 3.66 (d, J = 17.4 Hz, 1H).
    5-332 (A) δ 8.57 (d, J = 4.2 Hz, 1H), 7.65-7.75 (m, 2H), 7.45-7.6 (m, 4H),
    7.43 (bs, 1H), 7.33 (d, J = 7.8 Hz, 1H), 7.2-7.3 (m, 1H), 6.93 (bs, 1H),
    6.85 (d, J = 7.8 Hz, 1H), 4.71 (d, J = 4.8 Hz, 2H), 4.09 (d, J = 17.1 Hz, 1H),
    3.69 (d, J = 17.1 Hz, 1H), 2.90 (d, J = 3.6 Hz, 3H).
    5-335 (A) δ 10.29 (bs, 1H), 8.56 (d, J = 6.0 Hz, 1H), 8.18 (d, J = 8.1 Hz, 1H),
    7.15-7.75 (m, 8H), 4.79 (d, J = 5.4 Hz, 2H), 4.10 (d, J = 17.1 Hz, 1H),
    3.71 (d, J = 17.1 Hz, 1H), 2.75 (s, 6H).
    5-336 (A) δ 8.45-8.6 (m, 1H), 8.23 and 8.29 (s, 1H), 7.15-7.9 (m, 10H),
    4.65-4.75 (m, 2H), 4.0-4.2 (m, 1H), 3.6-3.8 (m, 1H),
    3.25 and 3.34 (s, 3H).
    5-337 (A) δ 8.45-8.6 (m, 1H), 7.15-8.05 (m, 10H), 4.65-4.75 (m, 2H),
    4.0-4.2 (m, 1H), 3.65-3.8 (m, 1H), 3.33 and 3.22 (s, 3H),
    2.19 and 1.87 (s, 3H).
    5-340 (B) δ 7.95-8.0 (m, 1H), 7.89 (dd, J = 8.0, 2.6 Hz, 1H),
    7.79 (dd, J = 7.8, 1.6 Hz, 1H), 7.52 (bs, 2H), 7.44 (t, J = 1.8 Hz, 1H),
    5.51 (s, 1H), 4.45-4.55 (m, 1H), 4.14 (dd, J = 20.2, 7.6 Hz, 1H),
    3.9-4.05 (m, 1H), 3.77 (dd, J = 17.4, 5.2 Hz, 1H).
    5-342 (B) δ 7.9-7.95 (bs, 2H), 7.53 (d, J = 1.8 Hz, 1H),
    7.44 (dd, J = 8.2, 1.8 Hz, 1H), 7.21 (bs, 2H), 7.14 (t, J = 1.8 Hz, 1H),
    3.75-3.9 (m, 3H), 0.30 (s, 9H).
    5-343 (B) δ 7.25-7.8 (m, 11H), 5.65 (t, J = 6.0 Hz, 1H), 4.10 (d, J = 17.2 Hz, 1H),
    3.7-3.85 (m, 3H).
    5-345 (A) δ 8.47 (s, 1H), 8.43 (d, J = 4.8 Hz, 1H), 7.95 (s, 1H), 7.6-7.85 (m, 5H),
    7.50 (bs, 2H), 7.43 (bs, 1H), 7.15-7.25 (m, 2H), 4.55 (d, J = 5.4 Hz, 2H),
    4.13 (d, J = 17.7 Hz, 1H), 3.77 (d, J = 17.7 Hz, 1H).
    5-346 (B) δ 7.91 (ddd, J = 8.6, 6.8, 1.8 Hz, 1H),
    7.78 (ddd, J = 8.6, 6.8, 1.8 Hz, 1H), 7.49 (d, J = 1.6 Hz, 2H),
    7.45 (t, J = 2.0 Hz, 1H), 6.84 (bs, 1H), 4.15-4.25 (m, 3H), 3.80 (bs, 1H).
    5-347 (B) δ 7.85-7.95 (m, 1H), 7.7-7.8 (m, 1H), 7.25-7.5 (m, 8H), 6.90 (bs, 1H),
    4.68 (d, J = 5.4 Hz, 2H), 4.16 (bs, 1H), 3.78 (bs, 1H).
    5-348 (B) δ 8.59 (bs, 1H), 8.11 (bs, 1H), 7.89 (bs, 1H), 7.71 (bs, 2H),
    7.2-7.5 (m, 5H), 4.80 (bs, 2H), 4.18 (d, J = 17.8 Hz, 1H),
    3.80 (d, J = 17.8 Hz, 1H).
    5-352 (A) δ 8.49 (d, J = 4.5 Hz, 1H), 7.65-7.75 (m, 1H), 7.51 (s, 2H),
    7.42 (s, 1H), 7.3-7.4 (m, 3H), 7.22 (dd, J = 7.5, 4.5 Hz, 1H),
    7.10 (bs, 1H), 4.76 (d, J = 4.5 Hz, 2H), 4.07 (d, J = 17.4 Hz, 1H),
    3.69 (d, J = 17.4 Hz, 1H), 2.33 (s, 6H).
    5-353 (A) δ 8.77 (d, J = 2.4 Hz, 1H), 7.73 (d, J = 8.1 Hz, 1H), 7.70 (s, 1H),
    7.60 (d, J = 8.1 Hz, 1H), 7.52 (bs, 2H), 7.43 (bs, 1H),
    7.33 (d, J = 2.4 Hz, 1H), 7.10 (t, J = 5.4 Hz, 1H), 4.81 (d, J = 5.4 Hz, 2H),
    4.12 (d, J = 17.4 Hz, 1H), 3.72 (d, J = 17.4 Hz, 1H).
    5-354 (A) δ 8.53 (d, J = 4.5 Hz, 1H), 7.55-7.8 (m, 5H), 7.53 (bs, 2H),
    7.43 (bs, 1H), 7.2-7.4 (m, 2H), 4.77 (d, J = 4.8 Hz, 2H),
    4.13 (d, J = 17.4 Hz, 1H), 3.74 (d, J = 17.4 Hz, 1H).
    5-356 (A) δ 7.4-7.6 (m, 6H), 6.17 (bs, 1H), 4.12 (d, J = 17.6 Hz, 1H),
    3.72 (d, J = 17.6 Hz, 1H), 3.55-3.7 (m, 4H), 3.53 (q, J = 7.1 Hz, 2H),
    2.47 (s, 3H), 1.20 (t, J = 7.1 Hz, 3H).
    5-357 (A) δ 7.4-7.6 (m, 6H), 5.97 (t, J = 5.6 Hz, 1H), 4.50 (t, J = 5.6 Hz, 1H),
    4.12 (d, J = 17.6 Hz, 1H), 3.72 (d, J = 17.6 Hz, 1H), 3.60 (t, J = 5.6 Hz, 2H),
    3.43 (s, 6H), 2.48 (s, 3H).
    5-358 (A) δ 7.4-7.6 (m, 6H), 5.75-6.0 (m, 2H), 5.27 (d, J = 17.1 Hz, 1H),
    5.21 (d, J = 10.2 Hz, 1H), 4.0-4.2 (m, 3H), 3.72 (d, J = 17.3 Hz, 1H),
    2.48 (s, 3H).
    5-359 (A) δ 8.79 (d, J = 2.1 Hz, 1H), 7.3-7.6 (m, 7H), 6.54 (t, J = 5.4 Hz, 1H),
    4.77 (d, J = 5.4 Hz, 2H), 4.12 (d, J = 17.6 Hz, 1H), 3.72 (d, J = 17.6 Hz, 1H),
    2.47 (s, 3H).
    5-360 (A) δ 8.54 (d, J = 5.0 Hz, 1H), 7.65-7.8 (m, 1H), 7.15-7.6 (m, 9H),
    4.74 (d, J = 5.0 Hz, 2H), 4.08 (d, J = 17.6 Hz, 1H), 3.72 (d, J = 17.6 Hz, 1H),
    2.50 (s, 3H).
    5-361 (B) δ 7.5-7.55 (m, 4H), 7.43 (d, J = 5.0 Hz, 1H), 7.42 (d, J = 1.8 Hz, 1H),
    6.07 (t, J = 6.4 Hz, 1H), 4.27 (d, J = 17.4 Hz, 1H), 4.05-4.15 (m, 2H),
    3.68 (dd, J = 17.4, 1.8 Hz, 1H), 2.46 (s, 3H).
    5-362 (B) δ 8.5-8.55 (m, 1H), 7.71 (td, J = 7.6, 1.6 Hz, 1H), 7.5-7.55 (m, 4H),
    7.42 (t, J = 1.6 Hz, 1H), 7.34 (d, J = 7.8 Hz, 1H), 7.2-7.3 (m, 3H),
    4.75 (d, J = 4.8 Hz, 2H), 4.27 (d, J = 17.2 Hz, 1H), 3.68 (d, J = 17.2 Hz, 1H),
    2.50 (s, 3H).
    5-364 (A) δ 7.3-7.6 (m, 6H), 6.07 (t, J = 6.3 Hz, 1H), 3.8-4.25 (m, 7H),
    3.41 (d, J = 16.8 Hz, 1H), 2.46 (s, 3H).
    5-365 (A) δ 8.52 (d, J = 3.8 Hz, 1H), 7.65-7.75 (m, 1H), 7.15-7.6 (m, 9H),
    4.75 (d, J = 4.6 Hz, 2H), 3.8-4.2 (m, 5H), 3.41 (d, J = 16.8 Hz, 1H),
    2.50 (s, 3H).
    5-366 (A) δ 7.3-7.55 (m, 6H), 6.83 (t, J = 6.5 Hz, 1H), 4.20 (d, J = 17.4 Hz, 1H),
    4.0-4.15 (m, 2H), 3.62 (d, J = 17.4 Hz, 1H), 2.40 (s, 3H), 2.30 (s, 3H).
    5-368 (B) δ 7.5-7.6 (m, 2H), 7.4-7.5 (m, 4H), 6.0-6.5 (m, 1H), 4.1-4.2 (m, 2H),
    3.53 (d, J = 3.2 Hz, 2H), 2.50 (s, 3H), 1.64 (d, J = 3.2 Hz, 2H),
    0.04 (s, 9H).
    5-369 (B) δ 8.55-8.6 (m, 1H), 7.7-7.8 (m, 1H), 7.5-7.55 (m, 3H),
    7.35-7.45 (m, 3H), 7.2-7.3 (m, 3H), 4.79 (d, J = 4.8 Hz, 2H),
    3.53 (d, J = 3.2 Hz, 2H), 2.55 (s, 3H), 1.64 (d, J = 5.8 Hz, 2H), 0.04 (s, 9H).
    5-370 (A) δ 7.47 (s, 1H), 7.45 (d, J = 7.8 Hz, 1H), 7.34 (d, J = 7.8 Hz, 1H),
    7.15-7.3 (m, 3H), 6.28 (t, J = 6.5 Hz, 1H), 4.07 (qd, J = 18.5, 6.5 Hz, 2H),
    3.61 (d, J = 16.2 Hz, 1H), 3.53 (d, J = 16.2 Hz, 1H), 2.40 (s, 3H),
    0.11 (s, 9H).
    5-371 (A) δ 8.50 (d, J = 5.1 Hz, 1H), 7.45-7.75 (m, 4H), 7.15-7.35 (m, 6H),
    4.72 (d, J = 5.1 Hz, 2H), 3.63 (d, J = 16.2 Hz, 1H), 3.54 (d, J = 16.2 Hz, 1H),
    2.48 (s, 3H), 0.11 (s, 9H).
    5-372 (A) δ 8.60 (d, J = 4.7 Hz, 1H), 7.15-7.75 (m, 9H), 6.05 (t, J = 6.0 Hz, 1H),
    4.77 (d, J = 16.8 Hz, 1H), 4.0-4.2 (m, 2H), 3.69 (d, J = 16.8 Hz, 1H),
    2.45 (s, 3H).
    5-373 (A) δ 8.60 (d, J = 4.9 Hz, 1H), 8.53 (d, J = 5.1 Hz, 1H), 7.15-7.8 (m, 13H),
    4.7-4.85 (m, 3H), 3.69 (d, J = 16.7 Hz, 1H), 2.48 (s, 3H).
    5-374 (A) δ 7.3-7.75 (m, 6H), 6.0-6.5 (br, 1H), 3.95-4.25 (m, 3H),
    3.70 (d, J = 17.1 Hz, 1H), 2.42 (s, 3H).
    5-375 (A) δ 8.55 (d, J = 4.8 Hz, 1H), 7.45-7.75 (m, 7H), 7.3-7.45 (m, 2H),
    7.15-7.3 (m, 1H), 4.74 (d, J = 5.1 Hz, 2H), 4.09 (d, J = 17.4 Hz, 1H),
    3.70 (d, J = 17.4 Hz, 1H), 2.49 (s, 3H).
    5-377 (A) δ 8.53 (d, J = 4.5 Hz, 1H), 7.55-7.8 (m, 8H), 7.15-7.4 (m, 2H),
    4.77 (d, J = 4.5 Hz, 2H), 4.08 (d, J = 17.4 Hz, 1H), 3.71 (d, J = 17.4 Hz, 1H).
    5-378 (A) δ 7.65-7.8 (m, 3H), 7.4-7.6 (m, 3H), 6.04 (t, J = 6.3 Hz, 1H),
    4.0-4.2 (m, 3H), 3.70 (d, J = 17.0 Hz, 1H), 2.47 (s, 3H).
    5-379 (A) δ 7.73 (bs, 1H), 7.71 (bs, 2H), 7.51 (s, 1H), 7.49 (d, J = 8.7 Hz, 1H),
    7.42 (d, J = 8.7 Hz, 1H), 6.2-6.3 (m, 1H), 4.08 (d, J = 17.4 Hz, 1H),
    3.71 (d, J = 17.4 Hz, 1H), 3.5-3.65 (m, 4H), 3.38 (s, 3H), 2.45 (s, 3H).
    5-380 (A) δ 7.74 (bs, 1H), 7.71 (bs, 2H), 7.51 (s, 1H), 7.50 (d, J = 8.4 Hz, 1H),
    7.42 (d, J = 8.4 Hz, 1H), 6.2-6.3 (m, 1H), 4.08 (d, J = 17.4 Hz, 1H),
    3.71 (d, J = 17.4 Hz, 1H), 3.55-3.65 (m, 4H), 3.53 (q, J = 7.2 Hz, 2H),
    2.46 (s, 3H), 1.20 (t, J = 7.2 Hz, 3H).
    5-381 (A) δ 7.73 (bs, 1H), 7.70 (bs, 2H), 7.51 (s, 1H), 7.50 (d, J = 8.4 Hz, 1H),
    7.41 (d, J = 8.4 Hz, 1H), 6.06 (t, J = 5.4 Hz, 1H), 4.50 (t, J = 5.4 Hz, 1H),
    4.08 (d, J = 16.8 Hz, 1H), 3.70 (d, J = 16.8 Hz, 1H), 3.59 (t, J = 5.4 Hz, 2H),
    3.43 (s, 6H), 2.46 (s, 3H).
    5-382 (A) δ 7.73 (bs, 1H), 7.71 (bs, 2H), 7.50 (s, 1H), 7.49 (d, J = 8.7 Hz, 1H),
    7.45 (d, J = 8.7 Hz, 1H), 6.47 (t, J = 5.4 Hz, 1H), 4.20 (d, J = 5.4 Hz, 2H),
    4.09 (d, J = 17.4 Hz, 1H), 3.80 (s, 3H), 3.72 (d, J = 17.4 Hz, 1H),
    2.46 (s, 3H).
    5-385 (A) δ 7.74 (bs, 1H), 7.70 (bs, 2H), 7.49 (s, 1H), 7.48 (d, J = 8.7 Hz, 1H),
    7.39 (d, J = 8.7 Hz, 1H), 6.06 (t, J = 5.4 Hz, 1H),
    5.92 (ddd, J = 15.9, 10.2, 5.4 Hz, 1H), 5.26 (d, J = 15.9 Hz, 1H),
    5.19 (d, J = 10.2 Hz, 1H), 4.08 (d, J = 17.4 Hz, 1H), 4.05 (t, J = 5.4 Hz, 2H),
    3.71 (d, J = 17.4 Hz, 1H), 2.45 (s, 3H).
    5-386 (A) δ 8.76 (d, J = 2.1 Hz, 1H), 7.73 (bs, 1H), 7.70 (bs, 2H), 7.49 (s, 1H),
    7.48 (d, J = 8.1 Hz, 1H), 7.42 (d, J = 8.1 Hz, 1H), 7.29 (d, J = 2.1 Hz, 1H),
    6.75 (t, J = 5.4 Hz, 1H), 4.76 (d, J = 5.4 Hz, 2H), 4.08 (d, J = 17.4 Hz, 1H),
    3.70 (d, J = 17.4 Hz, 1H), 2.44 (s, 3H).
    5-387 (A) δ 8.53 (d, J = 5.1 Hz, 1H), 7.65-7.8 (m, 4H), 7.53 (s, 3H),
    7.33 (d, J = 8.1 Hz, 1H), 7.15-7.3 (m, 2H), 4.75 (d, J = 4.8 Hz, 2H),
    4.08 (d, J = 17.1 Hz, 1H), 3.70 (d, J = 17.1 Hz, 1H), 2.51 (s, 3H).
    5-388 (A) δ 8.5-8.55 (m, 1H), 7.65-7.75 (m, 1H), 7.5-7.6 (m, 3H),
    7.2-7.45 (m, 6H), 4.75 (d, J = 4.8 Hz, 2H), 4.07 (d, J = 17.2 Hz, 1H),
    3.72 (d, J = 17.2 Hz, 1H), 2.51 (s, 3H), 2.39 (s, 3H).
    5-389 (A) δ 8.09 (s, 2H), 7.98 (s, 1H), 7.45-7.55 (m, 2H),
    7.38 (d, J = 8.4 Hz, 1H), 6.35 (bs, 1H), 4.21 (d, J = 17.4 Hz, 1H),
    4.0-4.15 (m, 2H), 3.77 (d, J = 17.4 Hz, 1H), 2.42 (s, 3H).
    5-390 (A) δ 8.53 (d, J = 4.2 Hz, 1H), 8.10 (s, 2H), 7.97 (s, 1H), 7.65-7.8 (m, 1H),
    7.54 (bs, 3H), 7.2-7.35 (m, 3H), 4.75 (d, J = 4.5 Hz, 2H),
    4.22 (d, J = 17.1 Hz, 1H), 3.77 (d, J = 17.1 Hz, 1H), 2.50 (s, 3H).
    5-391 (A) δ 8.52 (d, J = 5.1 Hz, 1H), 7.72 (t, J = 4.8 Hz, 1H), 7.52 (bs, 3H),
    7.15-7.35 (m, 4H), 7.07 (d, J = 9.3 Hz, 1H), 6.96 (d, J = 9.3 Hz, 1H),
    4.73 (d, J = 4.8 Hz, 2H), 4.10 (d, J = 17.4 Hz, 1H), 3.72 (d, J = 17.4 Hz, 1H),
    2.51 (s, 3H), 2.50 (s, 3H).
    5-392 (A) δ 8.53 (d, J = 4.8 Hz, 1H), 7.6-7.75 (m, 4H), 7.3-7.4 (m, 4H),
    7.15-7.35 (m, 2H), 4.77 (d, J = 5.1 Hz, 2H), 4.08 (d, J = 17.1 Hz, 1H),
    3.72 (d, J = 17.1 Hz, 1H), 2.52 (s, 3H), 2.50 (s, 3H).
    5-393 (A) δ 8.52 (d, J = 4.5 Hz, 1H), 7.70 (t, J = 4.8 Hz, 1H), 7.53 (bs, 1H),
    7.52 (bs, 2H), 7.15-7.45 (m, 6H), 4.74 (d, J = 4.8 Hz, 2H),
    4.12 (d, J = 17.4 Hz, 1H), 3.89 (s, 3H), 3.75 (d, J = 17.4 Hz, 1H),
    2.50 (s, 3H).
    5-394 (A) δ 8.52 (d, J = 5.1 Hz, 1H), 7.70 (t, J = 4.8 Hz, 1H), 7.52 (bs, 3H),
    7.15-7.35 (m, 5H), 7.13 (bs, 1H), 4.74 (d, J = 4.8 Hz, 2H),
    4.07 (d, J = 17.4 Hz, 1H), 3.73 (d, J = 17.4 Hz, 1H), 2.51 (s, 6H),
    2.50 (s, 3H).
    5-398 (A) δ 8.56 (d, J = 4.5 Hz, 1H), 7.72 (td, J = 7.5, 1 .5 Hz, 1H), 7.65 (s, 2H),
    7.45-7.6 (m, 4H), 7.39 (d, J = 7.8 Hz, 1H), 7.15-7.3 (m, 1H),
    4.72 (d, J = 5.1 Hz, 2H), 4.10 (d, J = 17.4 Hz, 1H), 3.71 (d, J = 17.4 Hz, 1H),
    2.46 (s, 3H).
    5-399 (B) δ 7.35-7.55 (m, 6H), 6.12 (bs, 1H), 4.18 (d, J = 17.2 Hz, 1H),
    3.65-3.75 (m, 3H), 2.4-2.55 (m, 5H).
    5-400 (B) δ 7.4-7.6 (m, 6H), 6.87 (d, J = 9.2 Hz, 1H), 5.9-6.0 (m, 1H),
    4.08 (dd, J = 17.2 Hz, 1H), 3.71 (d, J = 17.2 Hz, 1H), 2.48 (s, 3H).
    5-401 (B) δ 7.4-7.6 (m, 6H), 6.27 (d, J = 10.4 Hz, 1H), 5.6-5.8 (m, 1H),
    4.08 (d, J = 17.6 Hz, 1H), 3.71 (d, J = 17.6 Hz, 1H), 3.61 (s, 3H),
    2.50 (s, 3H).
    5-403 (A) δ 7.35-7.7 (m, 6H), 6.8 (s, 1H), 4.09 (d, J = 17.4 Hz, 1H),
    3.73 (d, J = 17.4 Hz, 1H), 3.55 (q, J = 5.4 Hz, 2H), 2.74 (t, J = 5.7 Hz, 2H),
    2.60 (bs, 4H), 2.45 (s, 3H), 1.79 (bs, 4H).
    5-404 (A) δ 7.35-7.6 (m, 6H), 6.77 (s, 1H), 4.10 (d, J = 17.4 Hz, 1H),
    3.73 (d, J = 17.4 Hz, 1H), 3.53 (q, J = 5.7 Hz, 2H), 2.57 (t, J = 6.0 Hz, 2H),
    2.47 (bs, 7H), 1.55-1.65 (m, 4H), 1.35-1.5 (m, 2H).
    5-405 (B) δ 7.45-7.55 (m, 5H), 7.43 (t, J = 1.8 Hz, 1H), 6.56 (d, J = 5.7 Hz, 1H),
    4.58 (ddd, J = 10.6, 8.4, 5.7 Hz, 1H), 4.09 (d, J = 17.2 Hz, 1H),
    3.95-4.05 (m, 1H), 3.8-3.9 (m, 1H), 3.71 (d, J = 17.2 Hz, 1H),
    3.5-3.65 (m, 2H), 2.85-2.9 (m, 1H), 2.48 (s, 3H), 2.0-2.15 (m, 1H).
    5-406 (B) δ 7.4-7.55 (m, 6H), 6.52 (t, J = 6.0 Hz, 1H), 5.35 (bs, 1H),
    4.8-4.95 (m, 1H), 4.09 (d, J = 17.4 Hz, 1H), 3.6-3.95 (m, 3H),
    3.75 (d, J = 17.4 Hz, 1H), 3.4-3.5 (m, 1H), 2.45 (s, 3H).
    5-407 (B) δ 7.5-7.55 (m, 5H), 7.43 (t, J = 1.8 Hz, 1H), 6.84 (d, J = 7.0 Hz, 1H),
    5.37 (d, J = 7.1 Hz, 1H), 4.09 (d, J = 17.2 Hz, 1H), 3.87 (s, 6H),
    3.72 (d, J = 17.2 Hz, 1H), 2.49 (s, 3H).
    5-409 (A) δ 9.80 and 8.65 (bs, 1H), 7.4-7.6 (m, 6H), 7.1 and 6.64 (bs, 1H),
    5.94 (bs, 1H), 5.2-5.5 (m, 2H), 3.95-4.45 (m, 5H),
    3.73 (d, J = 17.0 Hz, 1H), 2.42 (s, 3H).
    5-410 (B) δ 7.4-7.55 (m, 6H), 6.72 (bs, 1H), 6.37 (bs, 1H),
    4.65 (q, J = 7.4 Hz, 1H), 4.08 (d, J = 17.4 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H),
    3.25-3.35 (m, 2H), 2.45 (s, 3H), 1.47 (d, J = 7.4 Hz, 3H),
    1.16 (t, J = 7.4 Hz, 3H).
    5-414 (B) δ 8.19 (t, J = 6.0 Hz, 1H), 7.45-7.55 (m, 5H), 7.43 (t, J = 1.8 Hz, 1H),
    7.21 (d, J = 7.5 Hz, 1H), 4.93 (ddd, J = 11.9, 7.5, 4.2 Hz, 1H), 4.31 (bs, 1H),
    4.09 (d, J = 17.2 Hz, 1H), 4.0-4.1 (m, 1H), 3.65-3.9 (m, 3H),
    3.72 (d, J = 17.2 Hz, 1H), 2.47 (s, 3H), 2.15-2.25 (m, 1H), 1.8-1.9 (m, 1H).
    5-415 (B) δ 7.67 (t, J = 6.6 Hz, 1H), 7.3-7.55 (m, 6H), 7.11 (d, J = 8.1 Hz, 1H),
    4.9-5.0 (m, 1H), 4.3-4.45 (m, 2H), 4.09 (d, J = 17.2 Hz, 1H),
    3.8-3.9 (m, 2H), 3.73 (d, J = 17.2 Hz, 1H), 3.03 (s, 3H), 2.33 (s, 3H),
    2.2-2.4 (m, 2H).
    5-417 (B) δ 7.3-7.6 (m, 11H), 6.32 (d, J = 9.6 Hz, 1H), 6.24 (d, J = 9.6 Hz, 1H),
    4.07 (d, J = 17.2 Hz, 1H), 3.69 (d, J = 17.2 Hz, 1H), 3.59 (s, 3H),
    2.51 (s, 3H).
    5-420 (A) δ 8.77 (bs, 1H), 7.35-7.55 (m, 6H), 6.81 (s, 1H),
    6.37 (d, J = 9.3 Hz, 1H), 6.31 (s, 1H), 6.15-6.25 (m, 1H), 5.9-6.05 (m, 1H),
    4.07 (d, J = 17.3 Hz, 1H), 3.69 (d, J = 17.3 Hz, 1H), 2.43 (s, 3H).
    5-421 (A) δ 8.69 (d, J = 4.8 Hz, 1H), 7.51 (s, 5H), 7.43 (s, 1H),
    7.25 (d, J = 4.8 Hz, 1H), 6.86 (t, J = 5.7 Hz, 1H), 4.82 (d, J = 5.7 Hz, 2H),
    4.09 (d, J = 17.1 Hz, 1H), 3.70 (d, J = 17.1 Hz, 1H), 2.50 (s, 3H).
    5-423 (B) δ 7.72 (d, J = 3.3 Hz, 1H), 7.45-7.55 (m, 5H), 7.43 (t, J = 1.8 Hz, 1H),
    7.31 (d, J = 3.3 Hz, 1H), 6.78 (d, J = 7.7 Hz, 1H), 5.55-5.65 (m, 1H),
    4.08 (d, J = 17.2 Hz, 1H), 3.71 (d, J = 17.2 Hz, 1H), 2.47 (s, 3H),
    1.72 (d, J = 6.8 Hz, 3H).
    5-424 (A) δ 8.29 (d, J = 9.6 Hz, 1H), 7.4-7.6 (m, 7H), 7.12 (s, 1H), 7.01 (s, 1H),
    6.7-6.85 (m, 1H), 4.08 (d, J = 17.3 Hz, 1H), 3.70 (d, J = 17.3 Hz, 1H),
    2.38 (s, 3H).
    5-425 (B) δ 7.45-7.55 (m, 6H), 7.34 (bs, 1H), 6.89 (bs, 1H),
    6.58 (t, J = 4.8 Hz, 1H), 4.52 (d, J = 15.8 Hz, 2H), 4.07 (d, J = 17.2 Hz, 1H),
    3.69 (d, J = 17.2 Hz, 1H), 3.67 (s, 3H), 2.46 (s, 3H).
    5-426 (B) δ 8.33 (s, 1H), 7.92 (s, 1H), 7.45-7.55 (m, 4H),
    7.42 (t, J = 1.8 Hz, 1H), 7.25-7.35 (m, 2H), 6.45-6.55 (m, 1H),
    4.07 (d, J = 17.2 Hz, 1H), 3.71 (d, J = 17.2 Hz, 1H), 2.29 (s, 3H),
    1.87 (d, J = 6.6 Hz, 3H).
    5-427 (A) δ 8.40 (s, 1H), 8.07 (s, 1H), 7.2-7.6 (m, 7H), 6.9-7.1 (m, 1H),
    4.08 (d, J = 16.5 Hz, 1H), 3.70 (d, J = 16.5 Hz, 1H), 2.44 (s, 3H).
    5-428 (A) δ 7.97 (s, 1H), 7.4-7.65 (m, 6H), 4.54 (q, J = 8.3 Hz, 1H),
    4.08 (d, J = 17.3 Hz, 1H), 3.70 (d, J = 17.3 Hz, 1H), 2.49 (s, 3H).
    5-434 (A) δ 7.4-7.85 (m, 11H), 4.09 (d, J = 17.2 Hz, 1H), 3.72 (d, J = 17.2 Hz, 1H),
    2.53 (s, 3H).
    5-450 (A) δ 8.52 (d, J = 4.5 Hz, 1H), 7.69 (t, J = 7.8 Hz, 1H), 7.4-7.6 (m, 5H),
    7.15-7.35 (m, 4H), 4.73 (d, J = 4.8 Hz, 2H), 4.49 (s, 1H),
    3.99 (d, J = 16.8 Hz, 1H), 3.65-3.85 (m, 3H), 3.3-3.65 (m, 1H),
    3.33 (d, J = 16.8 Hz, 1H), 2.48 (s, 3H), 1.20 (t, J = 6.9 Hz, 3H),
    1.16 (t, J = 6.9 Hz, 3H).
    5-452 (A) δ 8.68 (s, 1H), 8.59 (s, 1H), 8.25 (s, 1H), 7.4-7.6 (m, 3H),
    6.06 (t, J = 6.2 Hz, 1H), 4.24 (d, J = 17.1 Hz, 1H), 4.0-4.2 (m, 2H),
    3.79 (d, J = 17.1 Hz, 1H), 2.47 (s, 3H).
    5-453 (A) δ 8.69 (s, 1H), 8.58 (s, 1H), 8.55 (d, J = 4.9 Hz, 1H), 8.26 (s, 1H),
    7.71 (td, J = 7.5, 1.5 Hz, 1H), 7.2-7.55 (m, 6H), 4.74 (d, J = 4.9 Hz, 2H),
    4.25 (d, J = 17.3 Hz, 1H), 3.79 (d, J = 17.3 Hz, 1H), 2.50 (s, 3H).
    5-455 (B) δ 8.54 (ddd, J = 4.9, 1.6, 0.9 Hz, 1H), 7.70 (td, J = 7.7, 1.8 Hz, 1H),
    7.5-7.55 (m, 3H), 7.43 (s, 2H), 7.33 (d, J = 7.7 Hz, 1H), 7.2-7.3 (m, 2H),
    4.74 (d, J = 4.9 Hz, 2H), 4.63 (bs, 2H), 4.02 (d, J = 17.2 Hz, 1H),
    3.69 (d, J = 17.2 Hz, 1H), 2.49 (s, 3H).
    5-456 (B) δ 7.61 (s, 2H), 7.45-7.55 (m, 2H), 7.39 (d, J = 7.9 Hz, 1H),
    6.28 (t, J = 6.6 Hz, 1H), 6.24 (bs, 1H), 4.0-4.15 (m, 2H),
    4.07 (d, J = 17.2 Hz, 1H), 3.69 (d, J = 17.2 Hz, 1H), 2.43 (s, 3H),
    1.50 (s, 9H).
    5-457 (B) δ 8.5-8.55 (m, 1H), 7.71 (td, J = 7.7, 1.7 Hz, 1H), 7.62 (s, 2H),
    7.45-7.55 (m, 3H), 7.34 (d, J = 7.9 Hz, 1H), 7.29 (t, J = 4.8 Hz, 1H),
    7.2-7.25 (m, 1H), 6.37 (bs, 1H), 4.75 (d, J = 5.0 Hz, 2H),
    4.07 (d, J = 17.2 Hz, 1H), 3.70 (d, J = 17.2 Hz, 1H), 2.50 (s, 3H),
    1.50 (s, 9H).
    5-460 (B) δ 8.77 (d, J = 2.0 Hz, 1H), 7.71 (d, J = 2.2 Hz, 1H), 7.3-7.55 (m, 6H),
    6.67 (t, J = 5.5 Hz, 1H), 4.76 (d, J = 5.7 Hz, 2H), 4.07 (d, J = 17.2 Hz, 1H),
    3.69 (d, J = 17.2 Hz, 1H), 2.44 (s, 3H).
    5-461 (B) δ 8.5-8.55 (m, 1H), 7.5-7.75 (m, 6H), 7.45 (dd, J = 8.6, 2.0 Hz, 1H),
    7.35 (d, J = 7.9 Hz, 1H), 7.29 (t, J = 4.8 Hz, 1H), 7.15-7.3 (m, 1H),
    4.75 (d, J = 4.8 Hz, 2H), 4.09 (d, J = 17.2 Hz, 1H), 3.71 (d, J = 17.2 Hz, 1H),
    2.72 (s, 3H).
    5-462 (B) δ 7.83 (d, J = 8.1 Hz, 1H), 7.74 (d, J = 1.7 Hz, 1H),
    7.62 (dd, J = 8.1, 1.7 Hz, 1H), 7.5-7.55 (m, 2H), 7.44 (t, J = 1.8 Hz, 1H),
    6.48 (bs, 2H), 4.08 (d, J = 17.2 Hz, 1H), 3.71 (d, J = 17.2 Hz, 1H).
    5-463 (B) δ 7.45-7.55 (m, 5H), 7.43 (t, J = 1.8 Hz, 1H), 7.27 (t, J = 5.1 Hz, 1H),
    7.21 (bs, 1H), 4.27 (d, J = 5.1 Hz, 2H), 4.07 (d, J = 17.2 Hz, 1H),
    3.9-4.0 (m, 2H), 3.70 (d, J = 17.2 Hz, 1H).
    5-468 (B) δ 8.16 (d, J = 1.7 Hz, 1H), 7.69 (dd, J = 8.1, 1.7 Hz, 1H),
    7.5-7.55 (m, 2H), 7.43 (t, J = 1.8 Hz, 1H), 7.42 (d, J = 8.1 Hz, 1H),
    7.21 (t, J = 5.3 Hz, 1H), 7.03 (bs, 1H), 4.24 (d, J = 5.3 Hz, 2H),
    4.07 (d, J = 17.2 Hz, 1H), 3.9-4.0 (m, 2H), 3.70 (d, J = 17.2 Hz, 1H).
    5-470 (B) δ 9.22 (bs, 1H), 8.40 (s, 2H), 8.11 (d, J = 1.6 Hz, 1H),
    7.74 (dd, J = 8.1, 1.6 Hz, 1H), 7.45-7.55 (m, 3H), 7.44 (t, J = 1.8 Hz, 1H),
    4.08 (d, J = 17.2 Hz, 1H), 3.71 (d, J = 17.2 Hz, 1H).
    5-471 (A) δ 7.35-7.6 (m, 6H), 5.87 (bs, 1H), 4.08 (d, J = 17.1 Hz, 1H),
    3.69 (d, J = 17.1 Hz, 1H), 3.01 (d, J = 4.8 Hz, 3H), 2.47 (s, 3H).
    5-472 (B) δ 7.5-7.55 (m, 4H), 7.4-7.5 (m, 2H), 5.8-6.15 (m, 1H),
    4.08 (d, J = 17.2 Hz, 1H), 3.84 (tdd, J = 15.0, 6.0, 4.2 Hz, 2H),
    3.70 (d, J = 17.2 Hz, 1H), 2.48 (s, 3H).
    5-473 (B) δ 7.4-7.55 (m, 6H), 6.42 (bs, 1H), 4.87 (d, J = 6.8 Hz, 2H),
    4.09 (d, J = 17.4 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H), 3.45 (s, 3H),
    2.50 (s, 3H).
    5-474 (B) δ 7.4-7.55 (m, 6H), 6.46 (bs, 1H), 4.92 (d, J = 6.8 Hz, 2H),
    4.08 (d, J = 17.4 Hz, 1H), 3.6-3.75 (m, 3H), 2.49 (s, 3H),
    1.25 (t, J = 6.8 Hz, 3H).
    5-475 (B) δ 7.5-7.55 (m, 4H), 7.4-7.5 (m, 2H), 6.40 (bs, 1H),
    4.92 (d, J = 6.8 Hz, 2H), 4.09 (d, J = 17.4 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H),
    3.57 (t, J = 6.6 Hz, 2H), 2.50 (s, 3H), 1.55-1.7 (m, 2H),
    0.95 (t, J = 7.4 Hz, 3H).
    5-476 (B) δ 7.4-7.55 (m, 6H), 6.51 (bs, 1H), 4.92 (d, J = 6.6 Hz, 2H),
    4.09 (d, J = 17.4 Hz, 1H), 3.90 (sep, J = 6.0 Hz, 1H), 3.71 (d, J = 17.4 Hz, 1H),
    2.47 (s, 3H), 1.22 (d, J = 6.0 Hz, 6H).
    5-477 (B) δ 7.4-7.55 (m, 6H), 6.50 (t, J = 7.2 Hz, 1H), 4.98 (d, J = 6.8 Hz, 2H),
    4.09 (d, J = 17.4 Hz, 1H), 3.85-3.95 (m, 2H), 3.70 (d, J = 17.4 Hz, 1H),
    2.50 (s, 3H), 1.95-2.05 (m, 2H).
    5-478 (B) δ 7.4-7.6 (m, 6H), 6.35-6.55 (m, 1H), 5.75-6.05 (m, 1H),
    4.96 (dd, J = 28.0, 7.2 Hz, 2H), 4.09 (d, J = 17.4 Hz, 1H), 3.65-4.2 (m, 3H),
    2.50 (s, 3H).
    5-479 (B) δ 7.45-7.55 (m, 6H), 6.56 (t, J = 7.2 Hz, 1H), 5.82 (t, J = 5.6 Hz, 1H),
    5.34 (t, J = 5.6 Hz, 1H), 5.03 (d, J = 5.6 Hz, 2H), 4.09 (d, J = 17.4 Hz, 1H),
    3.70 (d, J = 17.4 Hz, 1H), 2.51 (s, 3H), 2.30 (t, J = 7.4 Hz, 1H).
    5-481 (B) δ 7.4-7.6 (m, 6H), 6.65 (t, J = 7.2 Hz, 1H), 5.17 (d, J = 5.6 Hz, 2H),
    4.37 (s, 2H), 4.09 (d, J = 17.4 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H),
    2.51 (s, 3H).
    5-482 (B) δ 7.4-7.6 (m, 6H), 6.63 (bs, 1H), 4.97 (d, J = 6.4 Hz, 2H),
    4.09 (d, J = 17.4 Hz, 1H), 3.25-3.8 (m, 8H), 2.50 (s, 3H).
    5-483 (B) δ 7.4-7.6 (m, 6H), 6.41 (t, J = 7.2 Hz, 1H), 5.85-6.0 (m, 2H),
    5.2-5.5 (m, 3H), 4.95 (d, J = 7.2 Hz, 1H), 4.05-4.2 (m, 2H),
    3.70 (d, J = 17.4 Hz, 1H), 2.50 (s, 3H).
    5-484 (B) δ 7.4-7.55 (m, 6H), 6.51 (t, J = 7.2 Hz, 1H), 5.01 (d, J = 7.2 Hz, 2H),
    4.32 (d, J = 2.4 Hz, 2H), 4.09 (d, J = 17.4 Hz, 1H), 3.70 (t, J = 17.4 Hz, 1H),
    2.51 (s, 3H), 2.47 (t, J = 2.4 Hz, 1H).
    5-485 (B) δ 7.25-7.55 (m, 11H), 6.43 (bs, 1H), 5.01 (d, J = 6.8 Hz, 2H),
    4.65-4.75 (m, 2H), 4.08 (d, J = 17.4 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H),
    2.50 (s, 3H).
    5-486 (B) δ 7.5-7.55 (m, 4H), 7.4-7.45 (m, 2H), 6.95 (t, J = 7.2 Hz, 1H),
    5.41 (d, J = 7.2 Hz, 2H), 4.08 (d, J = 17.4 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H),
    2.48 (s, 3H), 2.12 (s, 3H).
    5-487 (A) δ 7.45-7.55 (m, 4H), 7.4-7.45 (m, 2H), 6.44 (bs, 1H),
    5.6-5.7 (m, 1H), 4.0-4.15 (m, 2H), 3.70 (d, J = 17.4 Hz, 1H),
    2.48 (s, 3H), 1.45 (d, J = 6.0 Hz, 3H).
    5-488 (A) δ 7.4-7.6 (m, 6H), 6.18 (d, J = 9.4 Hz, 1H), 5.6-5.7 (m, 1H),
    4.0-4.2 (m, 3H), 3.71 (d, J = 17.4 Hz, 1H), 2.48 (s, 3H),
    1.51 (d, J = 6.0 Hz, 3H).
    5-490 (B) δ 7.45-7.55 (m, 5H), 7.43 (t, J = 1.8 Hz, 1H), 6.57 (t, J = 4.8 Hz, 1H),
    4.09 (d, J = 17.2 Hz, 1H), 3.71 (d, J = 17.2 Hz, 1H), 3.55-3.7 (m, 10H),
    3.45-3.5 (m, 2H), 3.25 (s, 3H), 2.47 (s, 3H).
    5-492 (A) δ 7.45-7.65 (m, 6H), 5.87 (d, J = 8.4 Hz, 1H), 4.4-4.55 (m, 1H),
    4.18 (d, J = 6.9 Hz, 2H), 4.08 (d, J = 17.4 Hz, 1H), 3.69 (d, J = 17.4 Hz, 1H),
    2.47 (s, 3H), 2.10 (s, 3H), 1.29 (d, J = 6.9 Hz, 3H).
    5-493 (B) δ 7.35-7.55 (m, 6H), 6.21 (d, J = 5.8 Hz, 1H), 5.27 (bs, 1H),
    5.10 (bs, 1H), 4.44 (bs, 1H), 4.0-4.25 (m, 3H), 3.5-3.75 (m, 4H),
    2.46 (s, 3H), 1.25-1.3 (m, 3H).
    5-495 (A) δ 7.3-7.55 (m, 6H), 6.4-6.5 (m, 1H), 4.55-4.7 (m, 1H),
    3.65-4.15 (m, 6H), 2.39 (s, 3H), 2.2-2.45 (m, 1H), 1.8-2.0 (m, 1H).
    5-496 (A) δ 7.4-7.6 (m, 6H), 6.38 (d, J = 9.0 Hz, 1H), 5.2-5.35 (m, 1H),
    4.09 (d, J = 17.4 Hz, 1H), 3.95-4.15 (m, 1H), 3.71 (d, J = 17.4 Hz, 1H),
    3.6-3.75 (m, 1H), 2.46 (s, 3H), 1.85-2.0 (m, 2H), 1.4-1.75 (m, 4H).
    5-497 (A) δ 7.5-7.6 (m, 4H), 7.4-7.45 (m, 2H), 6.10 (bs, 1H),
    4.55 (d, J = 6.8 Hz, 2H), 4.08 (d, J = 17.4 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H),
    2.49 (s, 3H), 2.26 (s, 3H).
    5-500 (B) δ 7.5-7.6 (m, 4H), 7.43 (t, J = 1.8 Hz, 1H), 7.39 (d, J = 7.7 Hz, 1H),
    6.70 (t, J = 6.8 Hz, 1H), 4.83 (d, J = 6.8 Hz, 2H), 4.07 (d, J = 17.2 Hz, 1H),
    3.69 (d, J = 17.2 Hz, 1H), 2.46 (s, 3H), 2.40 (s, 3H).
    5-501 (B) δ 7.5-7.55 (m, 4H), 7.42 (t, J = 1.8 Hz, 1H), 7.41 (d, J = 8.8 Hz, 1H),
    7.20 (t, J = 6.8 Hz, 1H), 5.11 (d, J = 6.8 Hz, 2H), 4.67 (q, J = 7.2 Hz, 2H),
    4.09 (d, J = 17.2 Hz, 1H), 3.73 (d, J = 17.2 Hz, 1H), 2.46 (s, 3H),
    1.44 (t, J = 7.2 Hz, 3H).
    5-502 (B) δ 7.4-7.55 (m, 6H), 6.6-6.65 (m, 1H), 4.56 (d, J = 6.4 Hz, 2H),
    4.08 (d, J = 17.4 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H), 3.15 (q, J = 7.2 Hz, 6H),
    2.51 (s, 3H), 1.37 (t, J = 7.2 Hz, 9H).
    5-504 (B) δ 7.80 (bs, 1H), 7.45-7.55 (m, 3H), 7.43 (t, J = 1.8 Hz, 1H),
    7.3-7.4 (m, 4H), 6.95-7.05 (m, 2H), 6.59 (t, J = 5.3 Hz, 1H),
    4.05 (d, J = 17.2 Hz, 1H), 3.65-3.75 (m, 2H), 3.68 (d, J = 17.2 Hz, 1H),
    3.22 (t, J = 6.4 Hz, 2H), 2.44 (s, 3H).
    5-505 (B) δ 8.47 (d, J = 4.8 Hz, 2H), 7.45-7.55 (m, 4H), 7.43 (t, J = 1.8 Hz, 1H),
    7.34 (d, J = 8.4 Hz, 1H), 7.00 (t, J = 4.8 Hz, 1H), 6.85 (t, J = 5.3 Hz, 1H),
    4.08 (d, J = 17.2 Hz, 1H), 3.81 (td, J = 6.2, 5.3 Hz, 2H),
    3.71 (d, J = 17.2 Hz, 1H), 3.43 (t, J = 6.2 Hz, 2H), 2.44 (s, 3H).
    5-506 (B) δ 8.96 (d, J = 5.0 Hz, 2H), 7.61 (t, J = 5.0 Hz, 1H), 7.45-7.55 (m, 5H),
    7.43 (t, J = 1.8 Hz, 1H), 6.75 (t, J = 5.7 Hz, 1H), 4.08 (d, J = 17.2 Hz, 1H),
    3.95-4.1 (m, 2H), 3.85-3.95 (m, 2H), 3.70 (d, J = 17.2 Hz, 1H),
    2.48 (s, 3H).
    5-508 (B) δ 7.5-7.55 (m, 4H), 7.4-7.45 (m, 2H), 6.24 (bs, 1H),
    4.39 (d, J = 6.8 Hz, 2H), 4.08 (d, J = 17.4 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H),
    2.76 (q, J = 7.2 Hz, 2H), 2.49 (s, 3H), 1.15 (t, J = 7.2 Hz, 3H).
    5-509 (A) δ 7.5-7.55 (m, 5H), 7.35-7.5 (m, 2H), 6.37 (bs, 1H),
    4.44 (t, J = 6.6 Hz, 2H), 4.09 (d, J = 17.4 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H),
    3.2-3.4 (m, 2H), 2.48 (s, 3H).
    5-510 (B) δ 7.45-7.55 (m, 4H), 7.35-7.45 (m, 2H), 7.04 (bs, 1H),
    4.92 (d, J = 6.8 Hz, 2H), 4.44 (q, J = 8.8 Hz, 2H), 4.08 (d, J = 17.4 Hz, 1H),
    3.69 (d, J = 17.4 Hz, 1H), 2.46 (s, 3H), 2.18 (s, 3H).
    5-511 (B) δ 7.5-7.55 (m, 4H), 7.35-7.45 (m, 2H), 6.89 (bs, 1H),
    4.91 (d, J = 6.8 Hz, 2H), 4.15-4.3 (m, 2H), 4.08 (d, J = 17.4 Hz, 1H),
    3.78 (s, 3H), 3.70 (d, J = 17.4 Hz, 1H), 2.18 (s, 3H).
    5-521 (B) δ 7.4-7.55 (m, 6H), 6.70 (bs, 1H), 5.2-5.3 (m, 1H),
    4.03 (d, J = 17.4 Hz, 1H), 3.72 (d, J = 17.4 Hz, 1H), 3.5-3.6 (m, 2H),
    3.3-3.4 (m, 2H), 3.03 (q, J = 7.4 Hz, 2H), 2.41 (s, 3H),
    1.34 (t, J = 7.2 Hz, 3H).
    5-522 (B) δ 7.65 (t, J = 4.0 Hz, 1H), 7.4-7.6 (m, 6H), 6.23 (bs, 1H),
    4.40 (q, J = 8.4 Hz, 2H), 4.25-4.3 (m, 2H), 4.09 (d, J = 17.4 Hz, 1H),
    3.71 (d, J = 17.4 Hz, 1H), 2.50 (s, 3H).
    5-523 (A) δ 7.3-7.7 (m, 7H), 6.44 (d, J = 7.5 Hz, 1H), 4.75-4.9 (m, 1H),
    4.09 (d, J = 17.4 Hz, 1H), 3.84 (s, 3H), 3.71 (d, J = 17.4 Hz, 1H),
    2.47 (s, 3H), 1.44 (d, J = 6.9 Hz, 3H).
    5-524 (A) δ 7.4-7.65 (m, 7H), 6.79 (d, J = 7.3 Hz, 1H), 4.8-4.9 (m, 1H),
    4.05-4.2 (m, 3H), 3.83 (s, 3H), 3.69 (d, J = 17.4 Hz, 1H), 2.49 (s, 3H).
    5-525 (B) δ 7.35-7.55 (m, 6H), 6.15 (bs, 1H), 4.05-4.2 (m, 3H),
    3.70 (d, J = 17.2 Hz, 1H), 3.49 (q, J = 6.4 Hz, 2H), 2.4-2.5 (m, 5H),
    1.9-2.0 (m, 2H), 1.2-1.3 (m, 3H).
    5-527 (B) δ 7.45-7.6 (m, 5H), 7.4-7.45 (m, 1H), 7.07 (bs, 1H),
    4.05-4.3 (m, 3H), 3.74 (d, J = 17.4 Hz, 1H),
    3.35 and 3.47 (q, J = 6.8 Hz, 2H), 2.98 and 3.00 (s, 3H), 2.49 (s, 3H),
    1.1-1.3 (m, 3H).
    5-528 (B) δ 7.4-7.6 (m, 6H), 7.04 (bs, 1H), 4.24 (d, J = 4.0 Hz, 2H),
    4.10 (d, J = 17.4 Hz, 1H), 3.72 (d, J = 17.4 Hz, 1H), 3.44 (q, J = 6.8 Hz, 2H),
    3.33 (q, J = 6.8 Hz, 2H), 2.50 (s, 3H), 1.24 (t, J = 6.8 Hz, 3H),
    1.18 (t, J = 6.8 Hz, 3H).
    5-532 (A) δ 7.4-7.55 (m, 5H), 7.2-7.25 (m, 1H), 6.66 (bs, 1H), 6.16 (bs, 1H),
    4.53 (t, J = 5.0 Hz, 1H), 4.1-4.15 (m, 3H), 3.65-3.75 (m, 3H),
    3.5-3.6 (m, 2H), 3.46 (t, J = 5.0 Hz, 2H), 2.48 (s, 3H),
    1.22 (t, J = 6.8 Hz, 6H).
    5-538 (B) δ 7.4-7.55 (m, 6H), 6.63 (d, J = 7.8 Hz, 1H), 6.29 (bs, 1H),
    5.62 (bs, 1H), 4.6-4.8 (m, 1H), 4.08 (d, J = 17.4 Hz, 1H),
    3.70 (d, J = 17.4 Hz, 1H), 2.46 (s, 3H), 1.51 (d, J = 7.0 Hz, 3H).
    5-546 (A) δ 7.35-7.6 (m, 5H), 7.15-7.3 (m, 1H), 6.95-7.1 (m, 1H),
    6.6-6.8 (m, 2H), 5.52 (bs, 1H), 4.44 (bs, 1H), 4.05 (d, J = 17.3 Hz, 1H),
    3.75 (s, 3H), 3.65 (d, J = 17.3 Hz, 1H), 2.65-3.2 (m, 4H), 2.39 (s, 3H),
    1.2-2.2 (m, 4H).
    5-548 (A) δ 7.85 (bs, 1H), 7.45-7.55 (m, 6H), 7.03 (t, J = 6.6 Hz, 1H),
    6.56 (s, 1H), 5.72 (d, J = 6.6 Hz, 2H), 4.07 (d, J = 17.3 Hz, 1H),
    3.68 (d, J = 17.3 Hz, 1H), 2.39 (s, 3H).
    5-555 (B) δ 7.4-7.6 (m, 6H), 7.14 (s, 1H), 6.45 (bs, 1H), 4.6-4.7 (m, 2H),
    4.08 (d, J = 19.0 Hz, 1H), 3.70 (d, J = 19.0 Hz, 1H), 2.67 (s, 3H),
    2.45 (s, 3H).
    5-556 (B) δ 7.67 (s, 1H), 7.4-7.5 (m, 6H), 6.70 (bs, 1H), 4.75-4.8 (m, 2H),
    4.08 (d, J = 19.0 Hz, 1H), 3.70 (d, J = 19.0 Hz, 1H), 3.29 (s, 3H),
    2.44 (s, 3H).
    5-557 (A) δ 7.4-7.6 (m, 7H), 6.51 (t, J = 6.0 Hz, 1H),
    4.77 (dd, J = 6.0, 0.6 Hz, 2H), 4.08 (d, J = 17.2 Hz, 1H),
    3.69 (d, J = 17.2 Hz, 1H), 2.45 (s, 3H).
    5-558 (B) δ 8.59 (s, 1H), 7.45-7.55 (m, 5H), 7.43 (t, J = 1.8 Hz, 1H),
    6.81 (t, J = 5.5 Hz, 1H), 4.90 (d, J = 5.7 Hz, 2H), 4.09 (d, J = 17.2 Hz, 1H),
    3.72 (d, J = 17.2 Hz, 1H), 2.45 (s, 3H).
    5-559 (B) δ 8.0-8.05 (m, 2H), 7.35-7.6 (m, 9H), 6.29 (d, J = 6.8 Hz, 2H),
    4.05 (d, J = 17.4 Hz, 1H), 3.67 (d, J = 17.4 Hz, 1H), 2.38 (s, 3H).
    5-560 (A) δ 7.25-7.7 (m, 8H), 6.99 (d, J = 8.6 Hz, 1H), 6.35-6.5 (m, 1H),
    6.25 (bs, 1H), 4.06 (d, J = 17.4 Hz, 1H), 3.68 (d, J = 17.4 Hz, 1H),
    2.33 (s, 3H), 1.84 (s, 3H).
    5-561 (B) δ 8.75 (bs, 1H), 7.45-7.55 (m, 4H), 7.43 (t, J = 1.8 Hz, 1H),
    7.36 (d, J = 8.1 Hz, 1H), 4.08 (d, J = 17.2 Hz, 1H), 3.89 (s, 3H),
    3.70 (d, J = 17.2 Hz, 1H), 2.43 (s, 3H).
    5-563 (B) δ 7.5-7.6 (m, 5H), 7.44 (t, J = 1.8 Hz, 1H), 4.09 (d, J = 17.4 Hz, 1H),
    3.71 (d, J = 17.4 Hz, 1H), 3.41 (s, 3H), 2.52 (s, 3H).
    5-564 (B) δ 8.74 (s, 1H), 7.45-7.6 (m, 5H), 7.43 (t, J = 1.8 Hz, 1H),
    4.09 (d, J = 17.2 Hz, 1H), 3.72 (d, J = 17.2 Hz, 1H), 3.04 (s, 6H),
    2.51 (s, 3H).
    5-565 (A) δ 8.23 (bs, 1H), 7.35-7.65 (m, 11H), 4.10 (s, 2H),
    4.07 (d, J = 17.4 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H), 2.46 (s, 3H).
    5-572 (B) δ 8.10 (s, 1H), 7.45-7.6 (m, 5H), 7.43 (d, J = 8.1 Hz, 1H),
    5.20 (tqui, J = 20.1, 4.4 Hz, 1H), 4.5-4.75 (m, 4H),
    4.09 (d, J = 17.2 Hz, 1H), 3.71 (d, J = 17.2 Hz, 1H), 2.48 (s, 3H).
    5-573 (B) δ 8.15 (bs, 1H), 7.45-7.6 (m, 4H), 7.46 (d, J = 8.4 Hz, 1H),
    7.43 (t, J = 1.8 Hz, 1H), 5.05-5.25 (m, 1H), 4.55-4.75 (m, 2H),
    4.09 (d, J = 17.2 Hz, 1H), 3.65-3.8 (m, 3H), 2.47 (s, 3H).
    5-575 (B) δ 8.87 (bs, 1H), 7.4-7.55 (m, 6H), 4.08 (d, J = 17.2 Hz, 1H),
    3.70 (d, J = 17.2 Hz, 1H), 3.04 (bs, 6H), 2.44 (s, 3H).
    5-581 (A) δ 9.27 (t, J = 5.5 Hz, 1H), 8.74 (s, 1H), 8.59 (d, J = 5.0 Hz, 1H),
    7.4-7.7 (m, 7H), 7.15-7.3 (m, 2H), 4.65 (d, J = 5.5 Hz, 2H),
    4.08 (d, J = 17.3 Hz, 1H), 3.70 (d, J = 17.3 Hz, 1H), 2.53 (s, 3H).
    5-583 (B) δ 8.47 (bs, 1H), 7.4-7.55 (m, 6H), 4.08 (d, J = 17.2 Hz, 1H),
    3.70 (d, J = 17.2 Hz, 1H), 3.4-3.55 (m, 4H), 2.44 (s, 3H), 1.9-2.05 (m, 4H).
    5-585 (A) δ 7.3-7.7 (m, 11H), 7.18 (t, J = 7.2 Hz, 1H), 4.10 (d, J = 17.4 Hz, 1H),
    3.72 (d, J = 17.4 Hz, 1H), 2.54 (s, 3H).
    5-588 (A) δ 7.5-7.65 (m, 7H), 7.4-7.45 (m, 2H), 7.08 (t, J = 8.4 Hz, 2H),
    4.10 (d, J = 17.3 Hz, 1H), 3.72 (d, J = 17.3 Hz, 1H), 2.53 (s, 3H).
    5-591 (A) δ 8.20 (bs, 1H), 7.85 (s, 1H), 7.4-7.6 (m, 6H), 6.9-7.25 (m, 4H),
    4.10 (d, J = 17.0 Hz, 1H), 3.72 (d, J = 17.0 Hz, 1H), 2.55 (s, 3H).
    5-601 (A) δ 8.04 (s, 1H), 7.81 (d, J = 6.9 Hz, 1H), 7.4-7.65 (m, 9H),
    4.10 (d, J = 17.1 Hz, 1H), 3.72 (d, J = 17.1 Hz, 1H), 2.54 (s, 3H).
    5-603 (A) δ 8.77 (d, J = 7.4 Hz, 1H), 7.4-7.7 (m, 9H), 7.14 (t, J = 7.4 Hz, 1H),
    6.05 (d, J = 6.9 Hz, 1H), 4.15-4.3 (m, 1H), 4.10 (d, J = 17.3 Hz, 1H),
    3.71 (d, J = 17.3 Hz, 1H), 2.58 (s, 3H), 1.25 (d, J = 6.9 Hz, 6H).
    5-604 (A) δ 7.4-7.6 (m, 7H), 6.85-7.0 (m, 2H), 6.65-6.85 (m, 1H),
    4.11 (d, J = 17.1 Hz, 1H), 3.72 (d, J = 17.1 Hz, 1H), 2.55 (s, 3H).
    5-605 (A) δ 8.25-8.4 (m, 1H), 7.7-7.75 (m, 1H), 7.55-7.6 (m, 3H),
    7.5-7.55 (m, 2H), 7.4-7.45 (m, 1H), 7.05-7.15 (m, 1H), 6.7-6.85 (m, 1H),
    4.10 (d, J = 17.4 Hz, 1H), 3.72 (d, J = 17.4 Hz, 1H), 2.55 (s, 3H).
    5-609 (A) δ 7.89 (s, 1H), 7.2-7.7 (m, 9H), 4.10 (d, J = 17.1 Hz, 1H),
    3.71 (d, J = 17.1 Hz, 1H), 2.53 (s, 3H).
    5-610 (A) δ 7.45-7.65 (m, 8H), 7.44 (s, 1H), 7.17 (s, 1H),
    4.10 (d, J = 17.4 Hz, 1H), 3.72 (d, J = 17.4 Hz, 1H), 2.52 (s, 3H).
    5-611 (A) δ 8.36 (dd, J = 6.3, 2.7 Hz, 1H), 7.9-8.05 (m, 1H), 7.80 (s, 1H),
    7.4-7.6 (m, 6H), 7.32 (t, J = 9.0 Hz, 1H), 4.11 (d, J = 17.3 Hz, 1H),
    3.73 (d, J = 17.3 Hz, 1H), 2.52 (s, 3H).
    5-612 (A) δ 7.5-7.7 (m, 5H), 7.44 (t, J = 2.0 Hz, 1H), 7.03 (bs, 1H),
    6.80 (t, J = 7.2 Hz, 2H), 4.11 (d, J = 17.4 Hz, 1H), 3.72 (d, J = 17.4 Hz, 1H),
    2.54 (s, 3H).
    5-615 (A) δ 8.41 (bs, 1H), 7.4-7.65 (m, 6H), 6.74 (bs, 2H), 6.23 (bs, 2H),
    4.09 (d, J = 17.0 Hz, 1H), 3.73 (d, J = 17.0 Hz, 1H), 2.53 (s, 3H).
    5-617 (A) δ 7.4-7.75 (m, 9H), 6.38 (bs, 1H), 4.08 (d, J = 17.3 Hz, 1H),
    3.70 (d, J = 17.3 Hz, 1H), 2.53 (s, 3H).
    5-618 (A) δ 9.23 (bs, 1H), 7.4-7.7 (m, 8H), 4.10 (d, J = 17.3 Hz, 1H),
    3.72 (d, J = 17.4 Hz, 1H), 2.53 (s, 3H).
    5-619 (B) δ 9.32 (bs, 1H), 7.45-7.7 (m, 7H), 4.11 (d, J = 17.2 Hz, 1H),
    3.73 (d, J = 17.2 Hz, 1H), 2.60 (s, 3H).
    5-621 (B) δ 7.4-7.55 (m, 6H), 6.80 (bs, 1H), 4.56 (d, J = 6.4 Hz, 2H),
    4.09 (d, J = 17.0 Hz, 1H), 3.71 (d, J = 17.0 Hz, 1H), 3.16 (q, J = 7.2 Hz, 6H),
    2.51 (s, 3H), 1.37 (t, J = 7.2 Hz, 9H).
    5-629 (A) δ 8.4-8.6 (m, 3H), 7.95-8.1 (m, 1H), 7.61 (s, 3H), 7.4-7.55 (m, 3H),
    4.12 (d, J = 17.1 Hz, 1H), 3.73 (d, J = 17.1 Hz, 1H), 2.56 (s, 3H).
    5-630 (A) δ 8.29 (d, J = 7.8 Hz, 1H), 8.23 (s, 1H), 7.74 (t, J = 7.8 Hz, 1H),
    7.5-7.6 (m, 6H), 7.13 (d, J = 7.2 Hz, 1H), 4.11 (d, J = 17.1 Hz, 1H),
    3.73 (d, J = 17.1 Hz, 1H), 2.55 (s, 3H).
    5-631 (A) δ 8.32 (d, J = 8.1 Hz, 1H), 8.21 (s, 1H), 7.2-7.7 (m, 8H),
    4.11 (d, J = 17.4 Hz, 1H), 3.73 (d, J = 17.4 Hz, 1H), 2.55 (s, 3H).
    5-633 (A) δ 8.46 (s, 1H), 8.27 (d, J = 7.1 Hz, 1H), 7.76 (s, 1H), 7.3-7.6 (m, 7H),
    4.10 (d, J = 17.0 Hz, 1H), 3.72 (d, J = 17.0 Hz, 1H), 2.52 (s, 3H).
    5-634 (A) δ 8.72 (d, J = 2.4 Hz, 1H), 8.52 (dd, J = 8.4, 2.4 Hz, 1H), 7.99 (s, 1H),
    7.73 (d, J = 8.4 Hz, 1H), 7.4-7.65 (m, 6H), 4.11 (d, J = 17.3 Hz, 1H),
    3.73 (d, J = 17.3 Hz, 1H), 2.54 (s, 3H).
    5-635 (A) δ 8.31 (d, J = 5.4 Hz, 1H), 7.81 (s, 1H), 7.75-7.8 (m, 1H),
    7.4-7.6 (m, 7H), 4.10 (d, J = 17.4 Hz, 1H), 3.72 (d, J = 17.4 Hz, 1H),
    2.53 (s, 3H).
    5-637 (A) δ 8.82 (s, 1H), 8.41 (d, J = 4.8 Hz, 1H), 7.4-7.6 (m, 6H),
    6.90 (d, J = 4.8 Hz, 1H), 4.11 (d, J = 17.4 Hz, 1H), 3.73 (d, J = 17.4 Hz, 1H),
    2.53 (s, 3H), 2.45 (s, 3H).
    5-647 (B) δ 7.4-7.55 (m, 4H), 7.37 (d, J = 7.9 Hz, 1H), 6.37 (t, J = 6.0 Hz, 1H),
    4.0-4.15 (m, 2H), 4.06 (d, J = 17.2 Hz, 1H), 3.70 (d, J = 17.2 Hz, 1H),
    2.48 (s, 3H), 2.41 (s, 3H).
    5-648 (B) δ 8.5-8.6 (m, 1H), 7.71 (td, J = 7.7, 1.8 Hz, 1H), 7.45-7.6 (m, 6H),
    7.38 (d, J = 7.9 Hz, 1H), 7.2-7.3 (m, 1H), 4.73 (d, J = 5.1 Hz, 2H),
    4.07 (d, J = 17.2 Hz, 1H), 3.71 (d, J = 17.2 Hz, 1H), 2.71 (s, 3H),
    2.47 (s, 3H).
    5-649 (B) δ 8.55-8.65 (m, 1H), 7.84 (td, J = 7.7, 1.7 Hz, 1H), 7.3-7.8 (m, 8H),
    4.78 (d, J = 5.1 Hz, 2H), 4.05 (d, J = 17.2 Hz, 1H), 3.71 (d, J = 17.2 Hz, 1H),
    3.56 (bs, 1H), 2.49 (s, 3H).
    5-651 (B) δ 8.5-8.55 (m, 1H), 7.71 (td, J = 7.8, 1.8 Hz, 1H), 7.5-7.6 (m, 5H),
    7.34 (d, J = 7.9 Hz, 1H), 7.2-7.3 (m, 2H), 4.75 (d, J = 4.8 Hz, 2H),
    4.05 (d, J = 17.2 Hz, 1H), 3.92 (s, 3H), 3.71 (d, J = 17.2 Hz, 1H),
    2.49 (s, 3H).
    5-652 (B) δ 8.5-8.6 (m, 1H), 7.92 (td, J = 7.7, 1.8 Hz, 1H), 7.45-7.7 (m, 6H),
    7.39 (d, J = 7.7 Hz, 1H), 7.15-7.3 (m, 1H), 4.71 (d, J = 5.3 Hz, 2H),
    4.08 (d, J = 17.2 Hz, 1H), 3.73 (d, J = 17.2 Hz, 1H), 2.46 (s, 3H),
    1.57 (s, 9H).
    5-653 (B) δ 7.4-7.55 (m, 4H), 7.39 (d, J = 7.9 Hz, 1H), 6.37 (t, J = 5.9 Hz, 1H),
    4.0-4.15 (m, 2H), 4.05 (d, J = 17.2 Hz, 1H), 3.69 (d, J = 17.2 Hz, 1H),
    2.90 (s, 6H), 2.42 (s, 3H).
    5-654 (B) δ 8.5-8.6 (m, 1H), 7.71 (td, J = 7.7, 1.8 Hz, 1H), 7.45-7.55 (m, 5H),
    7.41 (t, J = 4.8 Hz, 1H), 7.36 (d, J = 7.7 Hz, 1H), 7.2-7.3 (m, 1H),
    4.73 (d, J = 5.0 Hz, 2H), 4.05 (d, J = 17.2 Hz, 1H), 3.70 (d, J = 17.2 Hz, 1H),
    2.90 (s, 6H), 2.48 (s, 3H).
    5-655 (A) δ 8.12 (s, 1H), 7.7-7.75 (m, 1H), 7.4-7.5 (m, 4H), 6.73 (bs, 1H),
    5.03 (d, J = 6.8 Hz, 2H), 4.13 (q, J = 8.4 Hz, 2H), 4.07 (d, J = 17.4 Hz, 1H),
    3.69 (d, J = 17.4 Hz, 1H).
    5-656 (A) δ 8.09 (bs, 1H), 7.35-7.75 (m, 5H), 6.27 (bs, 1H), 5.8-5.9 (m, 1H),
    3.8-4.2 (m, 3H), 3.69 (d, J = 17.4 Hz, 1H), 2.2-2.35 (m, 1H),
    1.9-2.1 (m, 3H).
    5-657 (B) δ 8.37 (d, J = 1.7 Hz, 1H), 7.83 (dd, J = 8.1, 1.8 Hz, 1H), 7.51 (bs, 2H),
    7.45 (t, J = 1.8 Hz, 1H), 7.43 (d, J = 8.1 Hz, 1H), 7.35 (bs, 1H),
    6.99 (bs, 1H), 4.23 (d, J = 17.8 Hz, 1H), 4.22 (d, J = 5.1 Hz, 2H),
    3.9-4.05 (m, 2H), 3.84 (d, J = 17.8 Hz, 1H).
    5-658 (A) δ 7.4-7.6 (m, 6H), 5.9-6.0 (m, 2H), 4.9-5.0 (m, 1H),
    4.11 (d, J = 17.4 Hz, 1H), 3.73 (d, J = 17.4 Hz, 1H), 3.53 (s, 3H),
    2.33 (s, 3H), 2.1-2.45 (m, 3H), 1.95-2.05 (m, 1H), 1.6-1.8 (m, 2H).
    5-662 (A) δ 8.41 (s, 1H), 7.4-7.55 (m, 6H), 5.67 (t, J = 6.3 Hz, 1H),
    4.12 (d, J = 17.4 Hz, 1H), 3.7-3.9 (m, 2H), 3.72 (d, J = 17.4 Hz, 1H),
    3.19 (s, 3H), 2.47 (s, 3H).
    5-667 (A) δ 8.78 (bs, 1H), 7.75 (s, 1H), 7.45-7.6 (m, 5H),
    7.43 (t, J = 1.5 Hz, 1H), 4.10 (d, J = 17.4 Hz, 1H), 3.73 (d, J = 17.4 Hz, 1H),
    2.51 (s, 3H).
    5-668 (A) δ 8.38 (dd, J = 4.8, 1.5 Hz, 1H), 8.04 (s, 1H),
    7.77 (dd, J = 7.8, 1.5 Hz, 1H), 7.65-7.65 (m, 5H), 7.57 (t, J = 1.8 Hz, 1H),
    7.12 (dd, J = 7.8, 4.8 Hz, 1H), 4.10 (d, J = 17.1 Hz, 1H),
    3.71 (d, J = 17.1 Hz, 1H), 2.58 (s, 3H).
    5-669 (A) δ 7.88 (d, J = 8.0 Hz, 1H), 7.74 (s, 1H), 7.64 (d, J = 8.0 Hz, 1H),
    7.52 (d, J = 1.5 Hz, 2H), 7.44 (t, J = 1.5 Hz, 1H), 6.38 (bs, 1H),
    6.02 (bs, 1H), 4.09 (d, J = 17.4 Hz, 1H), 3.67 (d, J = 17.4 Hz, 1H).
    5-670 (A) δ 7.66 (bs, 1H), 7.5-7.6 (m, 5H), 5.74 (bs, 2H),
    4.08 (d, J = 17.4 Hz, 1H), 3.68 (d, J = 17.4 Hz, 1H), 2.53 (s, 3H).
    5-672 (A) δ 8.09 (s, 2H), 7.97 (s, 1H), 7.5-7.6 (m, 3H), 5.79 (bs, 2H),
    4.21 (d, J = 17.4 Hz, 1H), 3.76 (d, J = 17.4 Hz, 1H), 2.53 (s, 3H).
    5-677 (A) δ 7.4-7.6 (m, 6H), 5.70 (bs, 2H), 4.09 (d, J = 17.4 Hz, 1H),
    3.70 (d, J = 17.4 Hz, 1H), 2.88 (q, J = 7.8 Hz, 2H), 1.26 (t, J = 7.8 Hz, 3H).
    5-679 (A) δ 7.35-8.25 (m, 6H), 6.97 (bs, 1H), 6.70 (t, J = 72.3 Hz, 1H),
    6.27 (bs, 1H), 4.10 (d, J = 17.1 Hz, 1H), 3.72 (d, J = 17.1 Hz, 1H).
    5-680 (A) δ 7.45-8.0 (m, 6H), 6.80 (bs, 2H), 4.10 (d, J = 17.4 Hz, 1H),
    3.20 (d, J = 17.4 Hz, 1H).
    5-682 (A) δ 11.3 (s, 1H), 7.4-8.85 (m, 8H), 4.15 (d, J = 17.4 Hz, 1H),
    3.75 (d, J = 17.4 Hz, 1H), 2.05 (s, 3H).
    5-684 (A) δ 7.81 (s, 1H), 7.75 (s, 1H), 7.69 (s, 1H), 7.5-7.55 (m, 2H),
    7.43 (d, J = 8.1 Hz, 1H), 6.06 (t, J = 6.6 Hz, 1H), 4.05-4.2 (m, 3H),
    3.72 (d, J = 17.4 Hz, 1H), 2.46 (s, 3H).
    5-685 (A) δ 6.58 (d, J = 6.3 Hz, 2H), 7.5-7.55 (m, 2H), 7.43 (d, J = 8.1 Hz, 1H),
    6.05 (t, J = 6.6 Hz, 1H), 4.05-4.2 (m, 3H), 3.68 (d, J = 17.4 Hz, 1H),
    2.45 (s, 3H).
    5-686 (A) δ 7.90 (dd, J = 6.3, 2.1 Hz, 1H), 7.75 (d, J = 5.7 Hz, 1H),
    7.5-7.55 (m, 2H), 7.43 (d, J = 8.1 Hz, 1H), 6.06 (t, J = 6.6 Hz, 1H),
    4.05-4.2 (m, 3H), 3.70 (d, J = 17.4 Hz, 1H), 2.44 (s, 3H).
    6-001 (A) δ 7.4-7.55 (m, 6H), 6.06 (bs, 1H), 5.39 (d, J = 28.6 Hz, 2H),
    4.24 (d, J = 6.0 Hz, 2H), 4.05 (d, J = 17.0 Hz, 1H), 3.67 (d, J = 17.3 Hz, 1H),
    2.49 (s, 3H).
    6-003 (A) δ 7.45-7.55 (m, 4H), 7.43 (s, 1H), 7.23 (d, J = 7.8 Hz, 1H),
    4.09 (d, J = 17.1 Hz, 1H), 3.71 (d, J = 17.1 Hz, 1H), 3.43 (bs, 2H),
    3.10 (bs, 2H), 2.32 (s, 3H), 1.26 (t, J = 6.9 Hz, 3H),
    1.03 (t, J = 6.9 Hz, 3H).
    6-005 (B) δ 7.98 (m, 1H), 7.2-7.6 (m, 6H), 4.09 (d, J = 17.0 Hz, 1H),
    3.18 (bs, 1H), 3.71 (d, J = 17.0 Hz, 1H), 3.40 (bs, 1H),
    2.43 and 2.33 (s, 3H), 2.12 and 1.66 (s, 3H), 1.23 and 1.08 (bs, 3H).
    6-006 (B) δ 7.2-7.6 (m, 6H), 4.05-4.15 (m, 1H), 3.75-3.9 and 3.35-3.5 (m, 2H),
    3.7 and 3.8 (m, 1H), 2.41 and 2.38 (s, 3H), 2.23 and 1.80 (s, 3H),
    2.00 and 1.77 (s, 3H), 1.25-1.3 and 1.05-1.1 (m, 3H).
    6-007 (B) δ 7.5-7.6 (m, 4H), 7.4-7.45 (m, 1H), 7.2-7.25 (m, 1H),
    3.2-4.7 (m, 4H), 4.10 (d, J = 17.0 Hz, 1H), 3.72 (d, J = 17.0 Hz, 1H),
    2.35 and 2.33 (s, 3H), 1.65-1.8 and 1.5-1.6 (m, 2H),
    1.4-1.5 and 1.1-1.25 (m, 2H), 1.0-1.05 and 0.75-0.85 (m, 3H).
    6-008 (B) δ 7.6-7.65 (m, 2H), 7.5-7.55 (m, 2H), 7.4-7.45 (m, 1H),
    7.3-7.35 (m, 1H), 4.65 (bs, 2H), 4.19 (bs, 2H), 4.09 (d, J = 17.0 Hz, 1H),
    3.71 (d, J = 17.0 Hz, 1H), 2.37 (s, 3H).
    6-010 (B) δ 7.5-7.55 (m, 4H), 7.3-7.5 (m, 7H), 4.85 (bs, 2H),
    4.08 (d, J = 17.0 Hz, 1H), 3.69 (d, J = 17.0 Hz, 1H), 3.35 (bs, 3H),
    2.27 (s, 3H).
    6-011 (B) δ 7.4-7.55 (m, 5H), 7.25-7.4 (m, 6H), 4.90 (bs, 2H),
    4.07 (d, J = 17.0 Hz, 1H), 3.68 (d, J = 17.0 Hz, 1H), 2.40 (s, 3H),
    1.88 (bs, 3H).
    6-012 (B) δ 7.4-7.55 (m, 5H), 7.25-7.4 (m, 6H), 4.43 (bs, 2H),
    4.07 (d, J = 17.0 Hz, 1H), 3.78 (bs, 3H), 3.68 (d, J = 17.0 Hz, 1H),
    2.38 (s, 3H).
    6-013 (B) δ 7.5-7.6 (m, 4H), 7.4-7.45 (m, 1H), 7.3-7.4 (m, 4H),
    7.15-7.25 (m, 2H), 4.93 (bs, 2H), 4.08 (d, J = 17.0 Hz, 1H),
    3.69 (d, J = 17.0 Hz, 1H), 3.05 (bs, 3H), 2.28 (s, 3H).
    6-015 (A) δ 8.82 (s, 1H), 7.35-7.6 (m, 6H), 7.08 (s, 1H), 4.75-5.2 (m, 2H),
    4.56 (bs, 2H), 4.08 (d, J = 17.4 Hz, 1H), 3.79 (d, J = 17.4 Hz, 1H),
    2.36 and 2.29 (s, 3H).
    6-016 (A) δ 8.80 and 8.77 (d, J = 7.8 Hz, 1H), 7.45-7.55 (m, 4H), 7.3-7.45 (m, 3H),
    4.85-5.2 (m, 1H), 4.2-4.7 (m, 2H), 4.07 and 4.08 (d, J = 17.4 Hz, 1H),
    3.75-4.0 (m, 1H), 3.69 (d, J = 17.4 Hz, 1H), 2.31 and 2.36 (s, 3H),
    2.25-2.3 (m, 1H).
    6-017 (B) δ 8.72 (s, 1H), 7.5-7.6 (m, 4H), 7.48 (s, 1H), 7.4-7.45 (m, 1H),
    7.18 (s, 1H), 5.03 (s, 2H), 4.07 (d, J = 17.0 Hz, 1H),
    3.68 (d, J = 17.0 Hz, 1H), 2.41 (s, 3H), 2.35 (s, 3H).
    6-018 (A) δ 8.72 (s, 1H), 7.45-7.55 (m, 4H), 7.4-7.45 (m, 1H),
    7.31 (d, J = 7.8 Hz, 1H), 7.20 (s, 1H), 5.04 (s, 2H),
    4.07 (d, J = 17.4 Hz, 1H), 3.68 (d, J = 17.4 Hz, 1H), 2.75 (q, J = 7.2 Hz, 2H),
    2.34 (s, 3H), 1.12 (t, J = 7.2 Hz, 3H).
    6-019 (B) δ 8.80 (s, 1H), 7.55-7.6 (m, 4H), 7.42 (s, 1H), 7.25-7.3 (m, 2H),
    5.26 (s, 2H), 4.07 (d, J = 17.0 Hz, 1H), 3.68 (d, J = 17.0 Hz, 1H),
    3.62 (s, 3H), 2.33 (s, 3H).
    6-021 (B) δ 8.5-8.6 (m, 1H), 7.65-7.75 (m, 1H), 7.4-7.6 (m, 5H),
    7.1-7.35 (m, 3H), 3.0-5.3 (m, 4H), 4.0-4.15 (m, 1H), 3.65-3.8 (m, 1H),
    2.37 and 2.34 (s, 3H), 1.25-1.35 and 1.0-1.1 (m, 3H).
    6-022 (B) δ 8.55-8.6 (m, 1H), 7.65-7.75 (m, 1H), 7.05-7.55 (m, 8H),
    4.3-5.3 (m, 2H), 4.0-4.15 (m, 1H), 2.9-4.1 (m, 2H), 3.65-3.75 (m, 1H),
    2.37 and 2.32 (s, 3H), 1.65-1.75 and 1.45-1.55 (m, 2H),
    0.95-1.0 and 0.65-0.75 (m, 3H).
    6-023 (B) δ 8.55-8.6 and 8.45-8.5 (m, 1H), 7.4-7.7 (m, 7H), 7.25-7.35 (m, 1H),
    7.1-7.2 (m, 1H), 4.90 (d, J = 16.0 Hz, 1H), 4.76 (d, J = 16.0 Hz, 1H),
    4.0-4.15 (m, 1H), 3.6-3.85 (m, 2H), 2.42 and 2.34 (s, 3H),
    1.23 and 1.06 (bs, 6H).
    6-024 (B) δ 8.5-8.6 (m, 1H), 7.05-7.7 (m, 9H), 4.83 and 4.39 (s, 2H),
    4.0-4.15 (m, 1H), 3.65-3.8 (m, 1H), 2.75-2.85 and 2.65-2.7 (m, 1H),
    2.36 and 2.33 (s, 3H), 0.75-0.9 and 0.45-0.6 (m, 4H).
    6-025 (B) δ 8.5-8.55 (m, 1H), 7.65-7.7 (m, 1H), 7.15-7.5 (m, 8H),
    4.45 and 4.16 (bs, 2H), 4.02 (d, J = 17.0 Hz, 1H), 3.63 (d, J = 17.0 Hz, 1H),
    2.38 (s, 3H), 1.54 (s, 9H).
    6-026 (B) δ 8.55-8.6 (m, 1H), 7.2-7.75 (m, 8H), 6.92 (d, J = 7.7 Hz, 1H),
    3.7-5.25 (br, 4H), 4.1-4.15 (m, 1H), 3.65-3.7 (m, 1H),
    2.04 and 2.26 (s, 3H).
    6-027 (A) δ 8.55 (bs, 1H), 6.95-7.75 (m, 9H), 5.07 and 4.93 (bs, 2H),
    4.53 and 4.48 (bs, 2H), 4.09 and 4.05 (d, J = 17.1 Hz, 1H),
    3.70 and 3.66 (d, J = 17.4 Hz, 1H), 3.47 and 3.14 (s, 3H),
    2.38 and 2.33 (s, 3H).
    6-028 (B) δ 8.5-8.6 (m, 1H), 7.6-7.75 (m, 1H), 7.05-7.55 (m, 8H),
    3.25-5.2 (m, 8H), 3.37 and 3.17 (s, 3H), 2.28 and 2.34 (s, 3H).
    6-029 (A) δ 8.5-8.6 (m, 1H), 6.95-7.75 (m, 9H), 4.98 (bs, 2H),
    4.58 and 4.37 (bs, 2H), 4.09 and 4.05 (d, J = 17.2 Hz, 1H),
    3.70 and 3.67 (d, J = 17.2 Hz, 1H), 2.38 and 2.31 (s, 3H),
    2.29 and 1.99 (s, 3H).
    6-030 (B) δ 8.5-8.65 (m, 1H), 7.15-7.8 (m, 8H), 7.0-7.05 (m, 1H),
    3.5-5.3 (m, 6H), 3.77 and 3.65 (s, 3H), 2.45 and 2.32 (s, 3H).
    6-031 (B) δ 8.5-8.65 (m, 1H), 7.2-7.8 (m, 8H), 6.9-7.0 (m, 1H), 4.0-5.2 (m, 5H),
    3.6-3.8 (m, 1H), 2.35 (s, 3H).
    6-032 (B) δ 8.5-8.65 (m, 1H), 7.0-7.8 (m, 9H), 5.8-6.0 and 5.55-5.75 (m, 1H),
    3.6-5.55 (m, 8H), 2.37 and 2.34 (s, 3H).
    6-033 (B) δ 8.5-8.65 (m, 1H), 7.05-7.75 (m, 9H), 3.5-5.3 (m, 6H), 2.37 (s, 3H),
    2.28 (s, 1H).
    6-034 (B) δ 8.45-8.5 (m, 1H), 7.6-7.65 (m, 1H), 7.4-7.55 (m, 6H),
    7.15-7.2 (m, 2H), 4.98 (s, 2H), 4.06 (d, J = 17.0 Hz, 1H),
    3.68 (d, J = 17.0 Hz, 1H), 2.41 (s, 3H), 2.39 (s, 3H).
    6-035 (A) δ 8.45-8.55 (m, 1H), 7.6-7.7 (m, 1H), 7.35-7.55 (m, 6H),
    7.1-7.25 (m, 2H), 4.99 (s, 2H), 4.06 (d, J = 19.0 Hz, 1H),
    3.67 (d, J = 19.0 Hz, 1H), 2.74 (q, J = 8.2 Hz, 2H), 2.39 (s, 3H),
    1.11 (t, J = 8.2 Hz, 3H).
    6-036 (A) δ 8.49 (d, J = 4.8 Hz, 1H), 7.63 (td, J = 7.8, 1.8 Hz, 1H),
    7.35-7.55 (m, 6H), 7.1-7.2 (m, 2H), 4.98 (s, 2H), 4.06 (d, J = 17.4 Hz, 1H),
    3.67 (d, J = 17.4 Hz, 1H), 2.70 (t, J = 7.2 Hz, 2H), 1.64 (hex, J = 7.2 Hz, 2H),
    1.55 (s, 3H), 0.89 (t, J = 7.2 Hz, 3H).
    6-037 (A) δ 8.49 (d, J = 5.1 Hz, 1H), 7.63 (td, J = 7.8, 1.8 Hz, 1H),
    7.35-7.55 (m, 6H), 7.1-7.25 (m, 2H), 4.99 (s, 2H),
    4.06 (d, J = 17.4 Hz, 1H), 3.77 (d, J = 17.4 Hz, 1H), 3.1-3.3 (m, 1H),
    2.42 (s, 3H), 1.13 (d, J = 6.6 Hz, 6H).
    6-038 (A) δ 8.53 (d, J = 4.8 Hz, 1H), 7.64 (td, J = 7.8, 1.8 Hz, 1H),
    7.45-7.55 (m, 5H), 7.4-7.45 (m, 1H), 7.15-7.3 (m, 2H), 5.16 (s, 2H),
    4.08 (d, J = 17.4 Hz, 1H), 3.68 (d, J = 17.4 Hz, 1H), 2.45 (s, 3H),
    1.9-2.0 (m, 1H), 0.95-1.05 (m, 2H), 0.7-0.8 (m, 2H).
    6-039 (A) δ 8.50 (d, J = 5.2 Hz, 1H), 7.55-7.65 (m, 1H), 7.4-7.55 (m, 6H),
    7.1-7.2 (m, 2H), 4.86 (s, 2H), 4.06 (d, J = 19.0 Hz, 1H),
    3.68 (d, J = 19.0 Hz, 1H), 2.44 (s, 3H), 1.34 (s, 9H).
    6-041 (B) δ 8.5-8.55 (m, 1H), 7.6-7.7 (m, 1H), 7.4-7.55 (m, 6H), 7.27 (s, 1H),
    7.15-7.2 (m, 1H), 6.47 (dd, J = 16.0, 10.0 Hz, 1H), 6.30 (d, J = 16.0 Hz, 1H),
    5.62 (d, J = 10.0 Hz, 1H), 5.10 (s, 2H), 4.07 (d, J = 17.0 Hz, 1H),
    3.69 (d, J = 17.0 Hz, 1H), 2.44 (s, 3H).
    6-042 (A) δ 8.54 (d, J = 0.9 Hz, 1H), 8.09 (d, J = 7.6 Hz, 1H), 7.15-7.75 (m, 13H),
    5.32 (s, 2H), 3.95 (d, J = 19.0 Hz, 1H), 3.58 (d, J = 19.0 Hz, 1H),
    2.34 (s, 3H).
    6-043 (A) δ 8.56 (d, J = 4.8 Hz, 1H), 7.65-7.7 (m, 1H), 7.5-7.55 (m, 4H),
    7.35-7.45 (m, 2H), 7.15-7.3 (m, 2H), 5.21 (s, 2H),
    4.09 (d, J = 17.4 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H), 3.58 (s, 3H),
    2.40 (s, 3H).
    6-044 (A) δ 8.56 (d, J = 3.9 Hz, 1H), 7.65 (td, J = 7.8, 1.8 Hz, 1H),
    7.35-7.55 (m, 6H), 7.15-7.3 (m, 2H), 5.21 (s, 2H),
    4.09 (d, J = 17.4 Hz, 1H), 4.00 (q, J = 7.2 Hz, 2H), 3.69 (d, J = 17.4 Hz, 1H),
    2.41 (s, 3H), 0.92 (t, J = 7.2 Hz, 3H).
    6-045 (A) δ 8.55 (d, J = 4.8 Hz, 1H), 7.67 (td, J = 7.8, 1.8 Hz, 1H),
    7.45-7.55 (m, 4H), 7.35-7.45 (m, 2H), 7.15-7.3 (m, 2H), 5.20 (s, 2H),
    4.7-4.85 (m, 1H), 4.08 (d, J = 17.4 Hz, 1H), 3.69 (d, J = 17.4 Hz, 1H),
    2.54 (s, 3H), 0.91 (d, J = 6.3 Hz, 6H).
    6-046 (B) δ 8.5-8.6 (m, 1H), 7.65-7.7 (m, 1H), 7.5-7.55 (m, 4H),
    7.4-7.45 (m, 2H), 7.25-7.3 (m, 1H), 7.15-7.2 (m, 1H), 5.23 (s, 2H),
    4.17 (d, J = 17.0 Hz, 1H), 3.75 (d, J = 6.8 Hz, 1H), 3.69 (d, J = 17.0 Hz, 1H),
    2.42 (s, 3H), 1.55-1.65 (m, 1H), 0.64 (d, J = 6.8 Hz, 6H).
    6-047 (B) δ 8.5-8.6 (m, 1H), 7.65-7.7 (m, 1H), 7.5-7.55 (m, 4H),
    7.4-7.45 (m, 2H), 7.25-7.3 (m, 1H), 7.15-7.25 (m, 1H), 5.23 (s, 2H),
    4.15-4.25 (m, 2H), 4.08 (d, J = 17.0 Hz, 1H), 3.70 (d, J = 17.0 Hz, 1H),
    3.3-3.4 (m, 2H), 2.42 (s, 3H).
    6-048 (B) δ 8.55-8.6 (m, 1H), 7.65-7.7 (m, 1H), 7.5-7.55 (m, 4H),
    7.4-7.5 (m, 2H), 7.25-7.3 (m, 1H), 7.15-7.25 (m, 1H), 5.23 (s, 2H),
    4.05-4.15 (m, 3H), 3.69 (d, J = 17.0 Hz, 1H), 3.2-3.25 (m, 2H),
    3.15 (s, 3H), 2.49 (s, 3H).
    6-049 (B) δ 8.5-8.6 (m, 1H), 7.65-7.7 (m, 1H), 7.45-7.55 (m, 4H),
    7.4-7.45 (m, 2H), 7.25-7.3 (m, 1H), 7.15-7.2 (m, 1H), 5.45-5.6 (m, 1H),
    5.23 (s, 2H), 5.0-5.1 (m, 2H), 4.4-4.45 (m, 2H), 4.18 (d, J = 17.0 Hz, 1H),
    3.69 (d, J = 17.0 Hz, 1H), 2.40 (s, 3H).
    6-050 (B) δ 8.54 (d, J = 4.8 Hz, 1H), 7.6-7.7 (m, 1H), 7.35-7.55 (m, 6H),
    7.15-7.25 (m, 2H), 5.13 (s, 2H), 4.07 (d, J = 17.0 Hz, 1H),
    3.68 (d, J = 17.0 Hz, 1H), 2.40 (s, 3H), 2.27 (s, 3H).
    6-051 (B) δ 8.55-8.6 (m, 1H), 7.6-7.65 (m, 1H), 7.45-7.5 (m, 5H),
    7.35-7.4 (m, 1H), 7.2-7.25 (m, 1H), 7.0-7.05 (m, 1H), 4.96 (s, 2H),
    4.05 (d, J = 17.0 Hz, 1H), 3.67 (d, J = 17.0 Hz, 1H), 3.43 (s, 3H),
    2.37 (s, 3H).
    6-053 (B) δ 8.65-8.7 (m, 1H), 7.65-7.8 (m, 2H), 7.5-7.55 (m, 2H),
    7.3-7.45 (m, 5H), 5.17 (s, 2H), 4.05 (d, J = 17.0 Hz, 1H),
    3.67 (d, J = 17.0 Hz, 1H), 3.50 (s, 6H), 2.46 (s, 3H).
    6-054 (B) δ 8.4-8.45 (m, 1H), 7.8-7.85 (m, 1H), 7.2-7.6 (m, 7H),
    4.2-5.3 (m, 2H), 4.05-4.15 (m, 1H), 3.65-3.75 (m, 1H), 3.05-3.15 (m, 2H),
    2.34 and 2.29 (s, 3H), 1.25-1.3 and 1.0-1.1 (m, 3H).
    6-055 (A) δ 8.6-8.65 (m, 2H), 7.5-7.55 (m, 4H), 7.43 (s, 1H), 7.25-7.3 (m, 3H),
    4.76 (s, 2H), 4.11 (d, J = 19.0 Hz, 1H), 3.71 (d, J = 19.0 Hz, 1H),
    2.45-2.5 (m, 1H), 2.34 (s, 3H), 1.2-1.3 (m, 4H).
    6-056 (A) δ 8.6-8.75 (m, 2H), 7.4-7.6 (m, 6H), 7.15-7.25 (m, 1H), 5.12 (s, 2H),
    4.06 (d, J = 17.0 Hz, 1H), 3.68 (d, J = 17.0 Hz, 1H), 2.69 (q, J = 7.9 Hz, 2H),
    2.43 (s, 3H), 1.11 (t, J = 7.9 Hz, 3H).
    6-069 (B) δ 7.8-7.9 (m, 2H), 7.67 (d, J = 7.6 Hz, 1H), 7.51 (bs, 2H),
    7.4-7.45 (m, 1H), 4.42 (s, 2H), 4.13 (d, J = 17.4 Hz, 1H),
    3.77 (d, J = 17.4 Hz, 1H), 3.22 (s, 3H).
    6-070 (A) δ 8.55 (d, J = 4.4 Hz, 1H), 7.92 (d, J = 7.8 Hz, 1H), 7.81 (s, 1H),
    7.15-7.7 (m, 7H), 4.93 (s, 2H), 4.52 (s, 2H), 4.13 (d, J = 17.0 Hz, 1H),
    3.76 (d, J = 17.0 Hz, 1H).
    6-073 (A) δ 8.55 (d, J = 4.7 Hz, 1H), 8.37 (bs, 1H), 8.02 (d, J = 8.5 Hz, 1H),
    7.91 (d, J = 8.5 Hz, 1H), 7.83 (bs, 1H), 7.69 (t, J = 7.7 Hz, 1H),
    7.52 (bs, 2H), 7.4-7.5 (m, 2H), 7.15-7.3 (m, 1H), 5.27 (s, 2H),
    4.15 (d, J = 17.3 Hz, 1H), 3.77 (d, J = 17.3 Hz, 1H).
    6-074 (B) δ 7.5-7.7 (m, 4H), 7.43 (s, 1H), 7.35-7.4 (m, 1H),
    4.50 (q, J = 8.4 Hz, 2H), 4.16 (d, J = 17.0 Hz, 1H), 3.75 (d, J = 17.0 Hz, 1H),
    2.44 (s, 3H), 2.15 (s, 3H).
    6-075 (B) δ 7.7-7.8 (m, 3H), 7.55-7.65 (m, 2H), 7.35-7.4 (m, 1H),
    4.50 (q, J = 8.6 Hz, 2H), 4.10 (d, J = 17.0 Hz, 1H), 3.71 (d, J = 17.0 Hz, 1H),
    2.44 (s, 3H), 2.16 (s, 3H).
    6-076 (B) δ 8.45-8.5 (m, 2H), 7.7-7.75 (m, 2H), 7.6-7.65 (m, 1H), 7.69 (s, 1H),
    7.4-7.45 (m, 2H), 7.15-7.2 (m, 2H), 4.97 (s, 2H), 4.06 (d, J = 17.0 Hz, 1H),
    3.68 (d, J = 17.0 Hz, 1H), 2.41 (s, 3H), 2.40 (s, 3H).
    6-077 (B) δ 7.5-7.6 (m, 4H), 7.43 (t, J = 1.8 Hz, 1H), 7.23 (d, J = 7.9 Hz, 1H),
    4.62 (q, J = 8.4 Hz, 2H), 4.08 (d, J = 17.2 Hz, 1H), 3.70 (d, J = 17.2 Hz, 1H),
    3.67 (s, 3H), 2.36 (s, 3H).
    6-078 (A) δ 8.79 and 8.75 (d, J = 1.8 Hz, 1H), 7.3-7.55 (m, 7H), 4.85-5.2 (m, 2H),
    4.53 and 4.50 (bs, 2H), 4.08 (d, J = 17.1 Hz, 1H), 3.69 (d, J = 17.1 Hz, 1H),
    3.47 and 3.14 (s, 3H), 2.36 and 2.25 (s, 3H).
    6-079 (A) δ 8.55 and 8.53 (d, J = 4.8 Hz, 1H),
    7.69 and 7.59 (td, J = 7.8, 1.8 Hz, 1H), 7.25-7.55 (m, 8H),
    4.8-5.25 (m, 2H), 4.57 and 4.49 (bs, 2H), 4.09 (d, J = 17.1 Hz, 1H),
    3.70 (d, J = 17.1 Hz, 1H), 3.65 and 3.27 (q, J = 6.9 Hz, 2H),
    2.37 and 2.34 (s, 3H), 1.26 and 1.08 (t, J = 6.9 Hz, 3H).
    6-080 (B) δ 8.58 (ddd, J = 4.9, 1.8, 0.9 Hz, 1H), 7.70 (td, J = 7.7, 1.8 Hz, 1H),
    7.35-7.55 (m, 7H), 7.18 (dd, J = 7.5, 4.9 Hz, 1H), 5.98 (q, J = 7.1 Hz, 1H),
    4.08 (d, J = 17.2 Hz, 1H), 3.70 (d, J = 17.2 Hz, 1H), 3.42 (s, 3H),
    2.43 (s, 3H), 1.90 (d, J = 7.0 Hz, 3H).
    6-081 (A) δ 8.21 (d, J = 4.2 Hz, 1H), 7.3-7.6 (m, 7H), 6.80 (dd, J = 8.1, 4.2 Hz, 1H),
    6.60 (d, J = 8.7 Hz, 1H), 4.05 (d, J = 17.1 Hz, 1H), 3.66 (d, J = 17.1 Hz, 1H),
    3.34 (s, 3H), 2.45 (s, 3H), 2.42 (s, 3H).
    6-082 (A) δ 8.22 (d, J = 4.8 Hz, 1H), 7.4-7.65 (m, 7H),
    6.78 (dd, J = 7.2, 4.8 Hz, 1H), 6.63 (d, J = 8.4 Hz, 1H),
    4.08 (d, J = 16.8 Hz, 1H), 3.70 (s, 3H), 3.69 (d, J = 16.8 Hz, 1H),
    3.40 (s, 3H), 2.46 (s, 3H).
    6-083 (A) δ 8.42 (s, 2H), 7.35-7.55 (m, 6H), 6.77 (t, J = 5.1 Hz, 1H),
    4.06 (d, J = 18.1 Hz, 1H), 3.67 (d, J = 18.1 Hz, 1H), 3.43 (s, 3H),
    2.44 (s, 3H), 2.43 (s, 3H).
    6-084 (A) δ 8.46 (bs, 1H), 8.40 (bs, 1H), 7.45-7.6 (m, 5H), 7.43 (s, 1H),
    6.74 (t, J = 4.8 Hz, 1H), 4.09 (d, J = 17.4 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H),
    3.69 (s, 3H), 3.53 (s, 3H), 2.46 (s, 3H).
    6-085 (B) δ 7.4-7.55 (m, 5H), 7.2-7.3 (m, 1H), 3.85-4.2 (m, 3H),
    3.6-3.8 (m, 1H), 2.5-2.65 (m, 2H), 2.32 and 2.30 (s, 3H),
    2.1-2.2 (m, 2H).
    6-086 (A) δ 7.4-7.6 (m, 6H), 4.09 (d, J = 17.2 Hz, 1H), 3.71 (d, J = 17.2 Hz, 1H),
    2.89 (s, 4H), 2.57 (s, 3H).
    6-089 (B) δ 7.45-7.6 (m, 4H), 7.4-7.45 (m, 1H), 7.2-7.3 (m, 1H),
    4.09 (d, J = 17.4 Hz, 1H), 3.71 (d, J = 17.4 Hz, 1H), 3.13 (bs, 3H),
    2.7-2.8 (m, 2H), 2.37 (bs, 3H), 1.15 (m, 3H).
    6-092 (B) δ 7.45-7.55 (m, 4H), 7.4-7.45 (m, 1H), 7.33 (d, J = 8.0 Hz, 1H),
    5.10 (s, 2H), 4.50 (s, 2H), 4.09 (d, J = 17.2 Hz, 1H), 3.6-3.75 (m, 3H),
    3.27 (q, J = 6.8 Hz, 2H), 2.36 (s, 3H), 1.25 (t, J = 7.0 Hz, 3H),
    1.10 (t, J = 7.0 Hz, 3H).
    6-093 (A) δ 7.5-7.7 (m, 4H), 7.44 (t, J = 2.0 Hz, 1H), 7.35 (d, J = 7.6 Hz, 1H),
    5.03 (s, 2H), 4.11 (d, J = 17.4 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H),
    3.50 (q, J = 7.0 Hz, 2H), 2.48 (s, 3H), 2.40 (s, 3H),
    1.15 (t, J = 7.0 Hz, 3H).
    6-094 (A) δ 7.5-7.6 (m, 4H), 7.44 (t, J = 1.8 Hz, 1H), 7.2-7.3 (m, 1H),
    5.14 and 4.62 (s, 2H), 4.05-4.15 (m, 2H), 3.6-3.75 (m, 2H),
    3.20 and 2.87 (s, 3H), 2.33 and 2.35 (s, 3H).
    6-095 (B) δ 7.3-7.6 (m, 6H), 5.15 (s, 2H), 3.95-4.2 (m, 3H),
    3.71 (d, J = 17.4 Hz, 1H), 2.48 (s, 3H), 2.40 (s, 3H).
    6-096 (B) δ 7.45-7.55 (m, 4H), 7.43 (t, J = 1.8 Hz, 1H), 7.24 (d, J = 8.1 Hz, 1H),
    4.12 (t, J = 5.5 Hz, 2H), 4.09 (d, J = 17.2 Hz, 1H), 3.71 (d, J = 17.2 Hz, 1H),
    3.66 (t, J = 5.5 Hz, 2H), 3.61 (s, 3H), 3.37 (s, 3H), 2.36 (s, 3H).
    6-097 (A) δ 7.4-7.55 (m, 5H), 7.2-7.3 (m, 1H), 5.18 and 4.87 (t, J = 4.6 Hz, 1H),
    3.65-4.2 (m, 8H), 3.20 and 2.89 (s, 3H), 2.34 and 2.32 (s, 3H).
    6-098 (A) δ 7.5-7.6 (m, 4H), 7.44 (t, J = 1.8 Hz, 1H), 7.37 (d, J = 7.8 Hz, 1H),
    5.12 (t, J = 4.6 Hz, 1H), 4.09 (d, J = 17.4 Hz, 1H), 3.8-3.95 (m, 6H),
    3.70 (d, J = 17.4 Hz, 1H), 2.43 (s, 3H), 2.33 (s, 3H).
    6-099 (A) δ 7.45-7.55 (m, 4H), 7.43 (t, J = 1.8 Hz, 1H), 7.25-7.3 (m, 1H),
    5.32 (t, J = 4.6 Hz, 1H), 3.9-4.15 (m, 7H), 3.69 (d, J = 17.4 Hz, 1H),
    3.62 (s, 3H), 2.38 (s, 3H).
    6-100 (A) δ 7.4-7.65 (m, 6H), 5.72 (dd, J = 7.2, 5.7 Hz, 1H),
    4.10 (d, J = 17.1 Hz, 1H), 4.0-4.15 (m, 1H), 3.75-3.85 (m, 1H),
    3.71 (d, J = 17.1 Hz, 1H), 2.49 (s, 3H), 2.3-2.45 (m, 1H), 2.22 (s, 3H),
    2.1-2.25 (m, 2H), 1.8-1.95 (m, 1H).
    6-101 (A) δ 7.35-7.6 (m, 5H), 6.6-7.3 (m, 2H), 3.65-4.45 (m, 7H),
    3.13 and 2.82 (d, J = 7.8 Hz, 3H), 2.3-2.35 (m, 3H).
    6-102 (A) δ 6.6-7.6 (m, 7H), 4.35-4.45 (m, 2H), 3.65-4.15 (m, 5H),
    2.3-2.45 (m, 6H).
    6-103 (A) δ 6.65-7.55 (m, 7H), 4.6-4.75 (m, 2H), 3.6-4.15 (m, 8H),
    2.37 and 2.35 (s, 3H).
    6-105 (B) δ 7.45-7.55 (m, 4H), 7.43 (t, J = 1.8 Hz, 1H), 7.37 (d, J = 8.8 Hz, 2H),
    7.14 (d, J = 8.1 Hz, 1H), 6.87 (d, J = 8.8 Hz, 2H), 5.00 (s, 2H),
    4.08 (d, J = 17.2 Hz, 1H), 3.81 (s, 3H), 3.68 (d, J = 17.2 Hz, 1H),
    3.58 (s, 3H), 2.29 (s, 3H).
    6-106 (B) δ 8.22 (d, J = 8.7 Hz, 2H), 7.59 (d, J = 8.7 Hz, 2H), 7.45-7.55 (m, 4H),
    7.43 (t, J = 1.8 Hz, 1H), 7.18 (d, J = 7.9 Hz, 1H), 5.15 (s, 2H),
    4.08 (d, J = 17.2 Hz, 1H), 3.70 (d, J = 17.2 Hz, 1H), 3.58 (s, 3H),
    2.16 (s, 3H).
    6-107 (B) δ 7.3-7.6 (m, 14H), 7.19 (d, J = 8.1 Hz, 1H), 5.11 (s, 2H),
    4.07 (d, J = 17.2 Hz, 1H), 3.68 (d, J = 17.2 Hz, 1H), 3.60 (s, 3H),
    2.37 (s, 3H).
    6-108 (A) δ 7.81 (bs, 1H), 7.4-7.55 (m, 5H), 7.2-7.3 (m, 1H), 6.56 (s, 1H),
    6.13 (s, 2H), 4.07 (d, J = 17.3 Hz, 1H), 3.68 (d, J = 17.3 Hz, 1H),
    2.28 (s, 3H), 1.23 (5, 9H).
    6-109 (B) δ 8.08 (dt, J = 7.5, 0.9 Hz, 1H), 7.89 (dt, J = 8.4, 0.9 Hz, 1H),
    7.4-7.6 (m, 7H), 7.14 (d, J = 8.1 Hz, 1H), 6.72 (s, 2H),
    4.06 (d, J = 17.2 Hz, 1H), 3.69 (s, 3H), 3.68 (d, J = 17.2 Hz, 1H),
    2.25 (s, 3H).
    6-111 (A) δ 8.56 (d, J = 4.2 Hz, 1H), 6.7-7.85 (m, 13H), 5.21 (s, 2H),
    4.00 (d, J = 17.4 Hz, 1H), 3.60 (d, J = 17.4 Hz, 1H), 2.40 (s, 3H).
    6-112 (A) δ 8.72 (d, J = 4.8 Hz, 2H), 7.4-7.6 (m, 6H), 7.22 (t, J = 4.8 Hz, 1H),
    5.33 (s, 2H), 4.10 (d, J = 17.1 Hz, 1H), 3.71 (d, J = 17.1 Hz, 1H),
    3.58 (s, 3H), 2.44 (s, 3H).
    6-113 (B) δ 7.82 (t, J = 6.0 Hz, 1H), 7.5-7.6 (m, 4H), 7.43 (bs, 1H),
    7.2-7.3 (m, 1H), 4.8-4.85 (m, 1H), 3.65-4.15 (m, 4H), 3.15-3.25 (m, 2H),
    2.5-2.6 (m, 1H), 2.34 (s, 3H), 1.85-2.1 (m, 3H).
    6-114 (A) δ 7.5-7.6 (m, 4H), 7.43 (t, J = 2.0 Hz, 1H), 7.25-7.35 (m, 1H),
    5.19 (s, 1H), 4.59 (s, 1H), 4.0-4.2 (m, 3H), 3.65-3.8 (m, 2H),
    3.27 (t, J = 6.4 Hz, 1H), 2.39 (bs, 3H).
    6-115 (A) δ 7.4-7.6 (m, 5H), 7.25-7.35 (m, 1H), 4.77 (s, 1H), 4.0-4.2 (m, 3H),
    3.70 (d, J = 17.4 Hz, 1H), 3.45 (t, J = 6.4 Hz, 1H), 3.13 (t, J = 6.4 Hz, 1H),
    2.97 (t, J = 6.4 Hz, 1H), 2.36 (m, 3H).
    6-119 (A) δ 7.4-7.55 (m, 6H), 4.08 (d, J = 17.4 Hz, 1H), 3.8-3.85 (m, 2H),
    3.69 (d, J = 17.4 Hz, 1H), 3.2-3.25 (m, 2H), 2.45-2.5 (m, 2H),
    2.2-2.35 (m, 8H).
    6-120 (B) δ 7.45-7.55 (m, 4H), 7.43 (t, J = 1.8 Hz, 1H), 7.30 (d, J = 7.9 Hz, 1H),
    4.08 (d, J = 17.2 Hz, 1H), 3.89 (s, 3H), 3.82 (s, 3H),
    3.69 (d, J = 17.2 Hz, 1H), 2.38 (s, 3H).
    6-121 (B) δ 7.45-7.55 (m, 4H), 7.43 (t, J = 1.8 Hz, 1H), 7.21 (d, J = 7.9 Hz, 1H),
    4.09 (d, J = 17.2 Hz, 1H), 3.77 (s, 3H), 3.70 (d, J = 17.2 Hz, 1H),
    2.84 (s, 6H), 2.40 (s, 3H).
    6-122 (B) δ 8.0-8.15 (m, 1H), 7.4-7.6 (m, 5H), 4.11 (d, J = 17.4 Hz, 1H),
    3.72 (d, J = 17.4 Hz, 1H), 2.68 (s, 3H), 2.33 (s, 6H).
    6-123 (B) δ 7.45-7.55 (m, 4H), 7.43 (t, J = 1.8 Hz, 1H), 7.31 (d, J = 7.9 Hz, 1H),
    4.8-4.9 (m, 1H), 4.76 (ddd, J = 47.6, 11.0, 2.4 Hz, 1H),
    4.58 (ddd, J = 46.0, 11.0, 2.7 Hz, 1H), 4.28 (dd, J = 11.2, 10.0 Hz, 1H),
    4.18 (dd, J = 11.2, 5.5 Hz, 1H), 4.08 (d, J = 17.2 Hz, 1H),
    3.70 (d, J = 17.2 Hz, 1H), 2.35 (s, 3H).
    6-124 (B) δ 7.5-7.6 (m, 4H), 7.43 (t, J = 1.8 Hz, 1H), 7.34 (d, J = 8.6 Hz, 1H),
    4.09 (d, J = 17.2 Hz, 1H), 3.75 (s, 3H), 3.70 (d, J = 17.2 Hz, 1H),
    3.14 (bs, 3H), 3.07 (bs, 3H), 2.44 (s, 3H).
    6-125 (B) δ 9.12 (t, J = 7.3 Hz, 1H), 7.5-7.6 (m, 4H), 7.43 (t, J = 1.8 Hz, 1H),
    7.23 (d, J = 8.2 Hz, 1H), 4.07 (d, J = 17.2 Hz, 1H), 3.68 (d, J = 17.2 Hz, 1H),
    3.39 (tq, J = 7.3, 7.1 Hz, 2H), 3.01 (s, 3H), 2.37 (s, 3H),
    1.24 (t, J = 7.1 Hz, 3H).
    6-126 (B) δ 9.65 (t, J = 6.2 Hz, 1H), 7.15-7.65 (m, 4H), 7.44 (t, J = 1.8 Hz, 1H),
    7.29 (d, J = 7.9 Hz, 1H), 4.09 (d, J = 17.2 Hz, 1H), 3.95-4.1 (m, 2H),
    3.71 (d, J = 17.2 Hz, 1H), 3.07 (s, 3H), 2.36 (s, 3H).
    6-130 (A) δ 7.2-7.7 (m, 6H), 6.15 (s, 1H), 5.15-5.35 (m, 1H), 4.5-4.8 (m, 1H),
    4.09 (d, J = 17.4 Hz, 1H), 3.6-4.3 (m, 3H), 3.48 and 3.03 (s, 3H),
    2.36 and 2.34 (s, 3H), 1.7-2.45 (m, 4H).
    6-131 (A) δ 7.35-7.6 (m, 6H), 5.65-5.75 (m, 1H), 4.05-4.2 (m, 1H),
    4.08 (d, J = 17.4 Hz, 1H), 3.7-3.85 (m, 1H), 3.70 (d, J = 17.4 Hz, 1H),
    2.51 (q, J = 6.0 Hz, 2H), 2.49 (s, 3H), 1.6-2.6 (m, 4H),
    1.08 (t, J = 6.0 Hz, 3H).
    6-132 (A) δ 7.5-7.6 (m, 4H), 7.4-7.45 (m, 2H), 5.78 (t, J = 6.3 Hz, 1H),
    4.05-4.15 (m, 2H), 3.75-3.85 (m, 1H), 3.71 (d, J = 17.4 Hz, 1H),
    2.7-2.9 (m, 1H), 2.50 (s, 3H), 2.25-2.4 (m, 1H), 2.1-2.25 (m, 2H),
    1.8-1.95 (m, 1H), 1.06 and 1.08 (d, J = 6.0 Hz, 6H).
    7-002 (A) δ 7.87 (bs, 1H), 7.78 (d, J = 8.1 Hz, 2H), 7.65 (d, J = 8.1 Hz, 2H),
    7.50 (bs, 2H), 7.43 (bs, 1H), 4.55-4.7 (m, 2H), 4.09 (d, J = 17.4 Hz, 1H),
    3.71 (d, J = 17.4 Hz, 1H).
    7-003 (A) δ 8.85 (s, 1H), 8.49 (bs, 1H), 7.86 (d, J = 8.4 Hz, 2H),
    7.67 (d, J = 8.7 Hz, 2H), 7.51 (bs, 2H), 7.43 (d, J = 1.8 Hz, 1H),
    7.40 (s, 1H), 5.13 (d, J = 4.8 Hz, 2H), 4.06 (d, J = 17.4 Hz, 1H),
    3.67 (d, J = 17.1 Hz, 1H).
    7-008 (A) δ 8.79 (s, 1H), 8.14 (bs, 1H), 7.35-7.5 (m, 7H),
    5.11 (d, J = 5.0 Hz, 2H), 4.06 (d, J = 17.4 Hz, 1H), 3.67 (d, J = 17.1 Hz, 1H),
    2.37 (s, 3H).
    7-009 (A) δ 9.06 (bs, 1H), 8.50 (d, J = 4.5 Hz, 1H), 7.75 (t, J = 7.2 Hz, 1H),
    7.2-7.6 (m, 8H), 5.04 (d, J = 4.2 Hz, 2H), 4.08 (d, J = 17.4 Hz, 1H),
    3.70 (d, J = 17.4 Hz, 1H), 2.44 (s, 3H).
    8-001 (A) δ 8.40 (d, J = 8.2 Hz, 2H), 7.74 (d, J = 8.2 Hz, 2H), 7.53 (s, 2H),
    7.43 (s, 1H), 7.04 (d, J = 4.7 Hz, 1H), 6.74 (d, J = 4.7 Hz, 1H),
    4.13 (d, J = 17.3 Hz, 1H), 3.89 (s, 3H), 3.74 (d, J = 17.3 Hz, 1H).
    8-002 (A) δ 8.22 (d, J = 8.0 Hz, 2H), 7.56 (s, 1H), 7.53 (s, 2H), 7.43 (s, 1H),
    7.03 (d, J = 4.7 Hz, 1H), 6.72 (d, J = 4.7 Hz, 1H), 4.12 (d, J = 17.3 Hz, 1H),
    3.84 (s, 3H), 3.72 (d, J = 17.3 Hz, 1H), 2.74 (s, 3H).
    8-003 (A) δ 8.19 (d, J = 8.1 Hz, 1H), 7.5-7.6 (m, 4H), 7.43 (s, 1H),
    7.04 (d, J = 4.8 Hz, 1H), 6.71 (d, J = 4.8 Hz, 1H), 4.23 (t, J = 7.2 Hz, 2H),
    4.12 (d, J = 17.1 Hz, 1H), 3.72 (d, J = 17.1 Hz, 1H), 2.73 (s, 3H),
    1.91 (hex, J = 7.2 Hz, 2H), 0.99 (t, J = 7.2 Hz, 3H).
    8-004 (A) δ 8.17 (d, J = 8.1 Hz, 1H), 7.45-7.65 (m, 4H), 7.41 (s, 1H),
    7.36 (t, J = 4.2 Hz, 1H), 4.12 (d, J = 17.4 Hz, 1H), 3.79 (s, 3H),
    3.74 (d, J = 17.4 Hz, 1H), 3.17 (d, J = 4.2 Hz, 2H), 2.69 (s, 3H).
    8-005 (A) δ 8.50 (s, 1H), 7.95 (d, J = 7.8 Hz, 1H), 7.68 (d, J = 6.6 Hz, 1H),
    7.4-7.6 (m, 5H), 6.32 (dd, J = 6.6, 4.2 Hz, 1H), 4.10 (d, J = 17.4 Hz, 1H),
    3.71 (d, J = 17.4 Hz, 1H), 3.67 (s, 3H), 2.68 (s, 3H).
    8-006 (A) δ 8.97 (s, 1H), 7.3-7.7 (m, 6H), 4.12 (d, J = 17.4 Hz, 1H),
    3.73 (d, J = 17.4 Hz, 1H), 3.62 (s, 3H), 2.36 (s, 3H).
    8-007 (A) δ 8.58 (d, J = 9.9 Hz, 1H), 8.08 (d, J = 7.8 Hz, 1H), 7.4-7.6 (m, 5H),
    7.30 (d, J = 9.9 Hz, 1H), 4.11 (d, J = 17.1 Hz, 1H), 4.00 (s, 3H),
    3.72 (d, J = 17.1 Hz, 1H), 2.67 (s, 3H).
    9-003 (B) δ 8.75 (d, J = 1.2 Hz, 1H), 8.7-8.75 (m, 1H), 8.14 (t, J = 1.8 Hz, 1H),
    7.5-7.6 (m, 2H), 7.45 (d, J = 8.6 Hz, 1H), 6.0-6.05 (m, 1H),
    4.05-4.2 (m, 3H), 3.74 (d, J = 17.2 Hz, 1H), 2.48 (s, 3H).
    9-008 (A) δ 7.97 (s, 1H), 7.45-7.55 (m, 2H), 7.35-7.4 (m, 1H),
    6.44 (t, J = 6.3 Hz, 1H), 4.40 (d, J = 17.6 Hz, 1H), 4.0-4.15 (m, 3H),
    2.42 (s, 3H).
    9-009 (A) δ 8.51 (dd, J = 5.1, 0.9 Hz, 1H), 7.96 (s, 1H),
    7.70 (td, J = 7.5, 1.5 Hz, 1H), 7.5-7.6 (m, 3H), 7.3-7.4 (m, 2H),
    7.15-7.25 (m, 1H), 4.74 (d, J = 4.8 Hz, 2H), 4.40 (d, J = 17.6 Hz, 1H),
    4.09 (d, J = 17.6 Hz, 1H), 2.50 (s, 3H).
    9-010 (B) δ 7.45-7.55 (m, 2H), 7.40 (d, J = 7.9 Hz, 1H), 7.04 (d, J = 4.0 Hz, 1H),
    6.89 (d, J = 4.0 Hz, 1H), 6.25 (bs, 1H), 4.05-4.15 (m, 2H),
    4.03 (d, J = 17.2 Hz, 1H), 3.74 (d, J = 17.2 Hz, 1H), 2.43 (s, 3H).
    9-011 (B) δ 8.5-8.55 (m, 1H), 7.70 (td, J = 7.5, 1.8 Hz, 1H), 7.45-7.65 (m, 3H),
    7.43 (t, J = 5.1 Hz, 1H), 7.34 (d, J = 7.9 Hz, 1H), 7.15-7.25 (m, 1H),
    7.04 (d, J = 3.8 Hz, 1H), 6.88 (d, J = 4.0 Hz, 1H), 4.73 (d, J = 5.0 Hz, 2H),
    4.04 (d, J = 17.2 Hz, 1H), 3.74 (d, J = 17.2 Hz, 1H), 2.48 (s, 3H).
    10-001  (A) δ 8.87 (d, J = 2.1 Hz, 1H), 8.25-8.3 (m, 2H),
    8.14 (dd, J = 8.1, 2.1 Hz, 1H), 7.51 (bs, 2H), 7.45 (d, J = 1.8 Hz, 1H),
    4.05-4.2 (m, 3H), 3.75 (d, J = 17.4 Hz, 1H).
    10-002  (A) δ 8.94 (bs, 1H), 8.88 (bs, 1H), 8.61 (d, J = 5.1 Hz, 1H),
    8.30 (d, J = 7.8 Hz, 1H), 8.12 (dd, J = 8.1, 2.1 Hz, 1H),
    7.68 (td, J = 7.8, 1.8 Hz, 1H), 7.51 (bs, 2H), 7.45 (t, J = 1.8 Hz, 1H),
    7.34 (d, J = 7.8 Hz, 1H), 7.2-7.25 (m, 1H), 4.80 (d, J = 5.4 Hz, 2H),
    4.12 (d, J = 17.4 Hz, 1H), 3.74 (d, J = 17.4 Hz, 1H).
    10-003  (A) δ 8.53 (d, J = 1.8 Hz, 1H), 8.48 (d, J = 8.4 Hz, 1H),
    7.74 (dd, J = 8.4, 1.8 Hz, 1H), 7.47 (bs, 3H), 4.0-4.2 (m, 2H),
    4.05 (d, J = 17.4 Hz, 1H), 3.68 (d, J = 17.4 Hz, 1H).
    10-004  (A) δ 9.01 (s, 1H), 8.17 (d, J = 8.4 Hz, 1H), 8.10 (d, J = 8.4 Hz, 1H),
    7.51 (s, 2H), 7.43 (s, 1H), 6.77 (t, J = 6.3 Hz, 1H),
    4.26 (d, J = 18.3 Hz, 1H), 4.05-4.25 (m, 2H), 3.89 (d, J = 18.3 Hz, 1H).
    10-005  (A) δ 9.09 (s, 1H), 8.57 (d, J = 5.1 Hz, 1H), 8.24 (d, J = 8.4 Hz, 1H),
    8.12 (d, J = 8.4 Hz, 1H), 7.86 (bs, 1H), 7.65-7.75 (m, 1H), 7.52 (s, 2H),
    7.43 (s, 1H), 7.2-7.35 (m, 2H), 4.78 (d, J = 4.2 Hz, 2H),
    4.28 (d, J = 18.3 Hz, 1H), 3.90 (d, J = 18.3 Hz, 1H).
    11-034  (A) δ 7.96 (t, J = 7.0 Hz, 1H), 7.88 (dd, J = 8.2, 1.6 Hz, 1H),
    7.81 (dd, J = 11.8, 1.4 Hz, 1H), 7.51 (bs, 2H), 7.4-7.45 (m, 1H),
    4.20 (dd, J = 18.2, 1.4 Hz, 1H), 3.82 (d, J = 18.2 Hz, 1H).
    11-038  (A) δ 7.89 (d, J = 8.1 Hz, 1H), 7.72 (s, 1H), 7.64 (d, J = 8.1 Hz, 1H),
    7.50 (s, 2H), 7.43 (s, 1H), 4.09 (d, J = 17.1 Hz, 1H), 3.95 (s, 3H),
    3.71 (d, J = 17.1 Hz, 1H).
    11-056  (A) δ 8.64 (d, J = 4.5 Hz, 1H), 8.06 (d, J = 8.4 Hz, 1H),
    7.75 (td, J = 7.7, 1.1 Hz, 1H), 7.5-7.6 (m, 4H), 7.35-7.45 (m, 2H),
    7.28 (t, J = 6.2 Hz, 1H), 5.48 (s, 2H), 4.11 (d, J = 17.1 Hz, 1H),
    3.72 (d, J = 17.1 Hz, 1H), 2.65 (s, 3H).
    11-057  (B) δ 8.4-8.45 (m, 1H), 7.75 (s, 1H), 7.5-7.65 (m, 5H), 7.44 (s, 1H),
    6.55 (s, 1H), 4.12 (d, J = 17.0 Hz, 1H), 3.73 (d, J = 17.0 Hz, 1H),
    2.37 (s, 3H).
    11-059  (A) δ 7.90 (d, J = 8.4 Hz, 1H), 7.4-7.7 (m, 5H), 4.11 (d, J = 17.4 Hz, 1H),
    3.91 (s, 3H), 3.72 (d, J = 17.4 Hz, 1H), 3.50 (q, J = 7.5 Hz, 2H),
    1.25 (t, J = 7.5 Hz, 3H).
    11-060  (A) δ 8.02 (d, J = 6.3 Hz, 1H), 7.75 (s, 1H), 7.67 (d, J = 6.3 Hz, 1H),
    7.51 (s, 2H), 7.43 (s, 1H), 4.95 (s, 2H), 4.12 (d, J = 17.4 Hz, 1H),
    3.97 (s, 3H), 3.74 (d, J = 17.4 Hz, 1H).
    11-062  (B) δ 8.07 (t, J = 0.8 Hz, 1H), 7.99 (ddd, J = 8.0, 1.6, 0.4 Hz, 1H),
    7.93 (dd, J = 7.4, 0.6 Hz, 1H), 7.48-7.52 (m, 2H), 7.46 (t, J = 1.4 Hz, 1H),
    4.11 (d, J = 16.8 Hz, 1H), 3.74 (dd, J = 17.4, 1.0 Hz, 1H).
    11-063  (B) δ 8.00 (s, 1H), 7.93 (d, J = 8.1 Hz, 1H), 7.87 (d, J = 8.1 Hz, 1H),
    7.51 (s, 2H), 7.4-7.5 (m, 1H), 4.12 (d, J = 16.7 Hz, 1H), 3.96 (s, 3H),
    3.74 (d, J = 16.7 Hz, 1H).
    11-071  (B) δ 8.03 (d, J = 8.0 Hz, 1H), 7.6-7.7 (m, 2H), 7.51 (s, 2H),
    7.4-7.5 (m, 1H), 4.09 (d, J = 17.2 Hz, 1H), 3.95 (s, 3H),
    3.70 (d, J = 17.2z, 1H).
    11-073  (A) δ 7.95-8.05 (m, 1H), 7.4-7.5 (m, 2H), 7.2-7.35 (m, 3H),
    4.06 (d, J = 17.1 Hz, 1H), 3.95 (s, 3H), 3.70 (d, J = 17.1 Hz, 1H),
    2.52 (s, 3H).
    11-092  (A) δ 7.94 (d, J = 8.8 Hz, 1H), 7.4-7.6 (m, 5H), 4.37 (q, J = 7.1 Hz, 2H),
    4.15 (d, J = 17.3 Hz, 1H), 3.73 (d, J = 17.3 Hz, 1H), 2.62 (s, 3H),
    1.40 (t, J = 7.1 Hz, 3H).
    11-095  (A) δ 7.94 (d, J = 8.8 Hz, 1H), 7.5-7.8 (m, 5H), 4.37 (q, J = 7.1 Hz, 2H),
    4.09 (d, J = 17.3 Hz, 1H), 3.70 (d, J = 17.3 Hz, 1H), 2.62 (s, 3H),
    1.40 (t, J = 7.1 Hz, 3H).
    11-102  (A) δ 7.85-7.95 (m, 1H), 7.35-7.6 (m, 5H), 6.91 (s, 1H),
    4.05 (d, J = 17.4 Hz, 1H), 3.67 (d, J = 17.4 Hz, 1H).
    11-105  (A) δ 8.06 (d, J = 8.4 Hz, 1H), 7.68 (dd, J = 8.4, 1.8 Hz, 1H),
    7.62 (d, J = 1.8 Hz, 1H), 7.50 (d, J = 1.5 Hz, 2H), 7.43 (t, J = 1.5 Hz, 1H),
    7.08 (s, 1H), 4.05 (d, J = 17.4 Hz, 1H), 3.67 (d, J = 17.4 Hz, 1H).
    11-107  (A) δ 7.68 (d, J = 1.8 Hz, 1H), 7.58 (dd, J = 8.1, 1.8 Hz, 1H),
    7.45-7.55 (m, 3H), 7.43 (t, J = 1.8 Hz, 1H), 5.22 (s, 2H),
    4.06 (d, J = 17.4 Hz, 1H), 3.68 (d, J = 17.4 Hz, 1H), 2.15 (s, 3H).
    11-112  (A) δ 8.08 (d, J = 8.4 Hz, 1H), 7.79 (d, J = 1.8 Hz, 1H),
    7.73 (d, J = 8.4 Hz, 1H), 7.49 (d, J = 1.5 Hz, 2H), 7.44 (t, J = 1.5 Hz, 1H),
    7.04 (s, 1H), 4.06 (d, J = 17.4 Hz, 1H), 3.67 (d, J = 17.4 Hz, 1H).
    11-113  (A) δ 7.84 (s, 1H), 7.55-7.7 (m, 2H), 7.50 (d, J = 1.5 Hz, 2H),
    7.43 (t, J = 1.5 Hz, 1H), 4.77 (s, 2H), 4.07 (d, J = 17.4 Hz, 1H),
    3.67 (d, J = 17.4 Hz, 1H).
    11-114  (A) δ 7.86 (s, 1H), 7.63 (d, J = 8.1 Hz, 1H), 7.4-7.55 (m, 4H),
    4.20 (s, 2H), 4.07 (d, J = 17.4 Hz, 1H), 3.67 (d, J = 17.4 Hz, 1H),
    2.17 (s, 3H).
    11-116  (A) δ 10.07 (s, 1H), 8.23 (s, 1H), 7.91 (d, J = 8.4 Hz, 1H),
    7.77 (d, J = 8.4 Hz, 1H), 7.50 (s, 2H), 7.44 (s, 1H),
    4.09(d, J = 17.4 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H).
    11-118  (A) δ 7.5-7.55 (m, 3H), 7.48 (dd, J = 8.1, 1.8 Hz, 1H),
    7.42 (t, J = 1.8 Hz, 1H), 7.38 (d, J = 8.1 Hz, 1H), 4.60 (s, 2H),
    4.07(d, J = 17.4 Hz, 1H), 3.67 (d, J = 17.4 Hz, 1H), 2.45 (s, 3H).
    11-119  (A) δ 7.45-7.55 (m, 3H), 7.47 (s, 2H), 7.42 (s, 1H), 4.74 (s, 2H),
    4.09 (d, J = 17.4 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H), 2.36 (s, 3H).
    11-122  (A) δ 9.35 (s, 1H), 7.4-7.45 (m, 5H), 7.2-7.3 (m, 1H),
    4.39 (q, J = 7.1 Hz, 2H), 4.21 (d, J = 17.3 Hz, 1H), 3.83 (d, J = 17.3 Hz, 1H),
    1.40 (t, J = 7.1 Hz, 3H).
    11-125  (A) δ 7.45-8.05 (m, 6H), 6.66 (t, J = 72.3 Hz, 1H), 4.08 (d, J = 17.4 Hz, 1H),
    3.71 (d, J = 17.4 Hz, 1H).
    11-126  (A) δ 6.7-7.5 (m, 6H), 6.50 (t, J = 74.1 Hz, 1H), 4.23 (bs, 2H),
    4.02 (d, J = 17.4 Hz, 1H), 3.63 (d, J = 17.4 Hz, 1H).
    11-127  (A) δ 7.2-7.95 (m, 6H), 6.57 (t, J = 73.2 Hz, 1H), 4.05 (d, J = 17.4 Hz, 1H),
    3.66 (d, J = 17.4 Hz, 1H).
    11-129  (A) δ 7.95 (q, J = 8.7 Hz, 1H), 7.66 (s, 1H), 7.5-7.6 (m, 4H),
    4.37 (q, J = 7.2 Hz, 2H), 4.10 (d, J = 17.4 Hz, 1H), 3.71 (d, J = 17.4 Hz, 1H),
    2.62 (s, 3H), 1.40 (t, J = 7.2 Hz, 3H).
    11-130  (A) δ 8.09 (s, 2H), 7.95-8.0 (m, 2H), 7.5-7.6 (m, 2H),
    4.38 (q, J = 7.2 Hz, 2H), 4.21 (d, J = 17.4 Hz, 1H), 3.76 (d, J = 17.4 Hz, 1H),
    2.63 (s, 3H), 1.41 (t, J = 7.2 Hz, 3H).
    14-004  (A) δ 7.40 (s, 1H), 7.35 (s, 2H), 5.99 (s, 1H), 5.65 (s, 1H).
    14-005  (B) δ 7.2-7.45 (m, 3H), 6.10 (s, 1H), 5.92 (s, 1H).
    14-006  (A) δ 7.40 (s, 2H), 7.33 (s, 1H), 5.63 (s, 1H), 5.45 (s, 1H),
    4.47 (s, 2H), 3.84 (q, J = 8.8 Hz, 2H).
    14-007  (B) δ 7.3-7.4 (m, 3H), 5.22 (s, 1H), 5.02 (s, 1H), 2.07 (s, 2H),
    0.04 (s, 9H).
    14-008  (A) δ 8.63 (d, J = 5.1 Hz, 1H), 7.69 (t, J = 8.0 Hz, 1H), 7.2-7.4 (m, 5H),
    5.99 (s, 1H), 5.64 (s, 1H).
    14-009  (A) δ 7.25-7.6 (m, 3H), 6.04 (s, 1H), 5.80 (s, 1H).
    14-010  (B) δ 7.24 (s, 1H), 7.20 (s, 1H), 7.14 (s, 1H), 5.97 (s, 1H),
    5.77 (s, 1H), 2.36 (s, 3H).
    14-012  (A) δ 7.40 (d, J = 6.3 Hz, 2H), 6.04 (s, 1H), 5.79 (s, 1H).
    14-013  (B) δ 7.54 (s, 2H), 6.06 (s, 1H), 5.83 (s, 1H).
    14-016  (A) δ 7.70 (s, 1H), 7.52 (s, 2H), 6.04 (s, 1H), 5.80 (s, 1H).
    14-018  (A) δ 7.65 (s, 1H), 7.62 (s, 1H), 7.58 (s, 1H), 6.11 (s, 1H),
    5.87 (s, 1H).
    14-020  (A) δ 7.69 (d, J = 6.3 Hz, 1H), 7.58 (d, J = 5.7 Hz, 1H), 6.10 (s, 1H),
    5.83 (s, 1H).
    14-021  (A) δ 7.2-7.45 (m, 4H), 5.98 (s, 1H), 5.78 (s, 1H),
    2.93 (dd, J = 10.8, 7.8 Hz, 1H), 2.01 (dd, J = 10.8, 7.8 Hz, 1H),
    1.87 (t, J = 7.8 Hz, 1H).
    14-022  (B) δ 7.35-7.45 (m, 2H), 7.2-7.3 (m, 2H), 6.09 (d, J = 53.2 Hz, 1H),
    6.03 (s, 1H), 5.82 (s, 1H).
    14-023  (B) δ 7.2-7.5 (m, 6H), 6.95-7.1 (m, 3H), 5.93 (s, 1H), 5.77 (s, 1H),
    5.17 (s, 2H).
    14-024  (A) δ 7.57 (d, J = 2.7 Hz, 1H), 7.2-7.55 (m, 4H), 6.9-7.15 (m, 3H),
    5.96 (s, 1H), 5.78 (s, 1H), 5.19 (s, 2H).
    14-025  (A) δ 8.27 (s, 1H), 7.99 (s, 1H), 7.15-7.6 (m, 4H), 6.00 (s, 1H),
    5.83 (s, 1H).
    14-026  (A) δ 7.74 (s, 1H), 7.69 (d, J = 7.7 Hz, 1H), 7.58 (d, J = 7.7 Hz, 1H),
    7.46 (t, J = 7.7 Hz, 1H), 6.04 (s, 1H), 5.82 (s, 1H).
    14-027  (A) δ 8.34 (s, 1H), 8.25 (d, J = 8.0 Hz, 1H), 7.79 (d, J = 8.0 Hz, 1H),
    7.60 (t, J = 8.0 Hz, 1H), 6.14 (s, 1H), 5.93 (s, 1H).
    • TEST EXAMPLES
  • Next, usefulness of the compound of the present invention as a pesticide is specifically explained in the following Test Examples to which the present invention is not limited.
    • Test Example 1 Insecticidal Test Against Cabbage Moth
  • A 10% emulsifiable concentrate (depending on the compounds, 10% wettable powder was applied for the test) of the compound of the present invention was diluted with water containing a spreading agent to prepare a chemical solution with a concentration of 500 ppm. To the chemical solution was dipped leaves of cabbage for about 10 seconds, and after air-drying, they were placed in a laboratory dish, then 5-cabbage moth (Plutella xylostella) in the stage of second instar larva per the dish were released therein, and the dish was covered with a lid and contained at a thermostat chamber at 25° C. A number of dead insect(s) after 6 days was counted and a rate of dead insects was calculated by the following calculation equation. Incidentally, the test was carried out with two districts.

  • Rate of dead insects (%)=(Number of dead insects/Number of released insects)×100
  • As a result, the following compounds showed an insecticidal rate of 80% or more among the compounds tested.
    The compounds of the present invention:
    No. 1-005, 1-006, 1-015, 1-016, 1-025, 1-031, 1-040, 1-041, 1-053, 1-055˜1-058, 1-062˜1-074, 1-076, 1-077, 1-079˜1-096, 1-098, 1-101, 1-102, 1-104˜1-110, 1-113, 1-114, 1-116˜1-140, 1-145˜1-147, 1-149˜1-157, 1-159˜1-161, 1-166˜1-168, 1-171, 1-172, 1-174, 1-175, 1-176*, 1-177*, 1-178˜1-184, 1-185*, 1-187, 1-188*, 1-189*, 1-190, 1-194, 1-196, 1-199, 1-206*, 1-207, 1-209, 1-212, 1-214, 1-215, 1-225, 1-226, 2-001˜2-005, 2-01˜2-021, 2-022*, 2-024˜2-027, 2-028**, 2-029**, 2-030, 2-031, 2-032*, 2-033, 2-034**, 2-035**, 2-036˜2-041, 2-042**, 2-043, 2-044**, 2-045**, 2-046**, 2-047*, 2-048**, 2-049**, 2-050*, 2-051*, 2-052*, 2-053, 2-054**, 2-055**, 2-057*, 2-058*, 2-059*, 2-060*, 2-061*, 2-062*, 2-063*, 2-064, 2-065*, 2-066, 2-067*, 2-068*, 2-069, 3-002˜3-004, 3-006, 3-007, 3-012, 3-018, 3-023, 3-025˜3-028, 3-030˜3-035, 3-037, 3-038, 3-040, 3-043, 3-044, 3-046, 3-047, 3-050, 3-055, 3-058*, 3-060, 3-061*, 3-062˜3-067, 3-068*, 3-069, 3-070*, 3-071*, 3-073˜3-075, 3-077˜3-081, 3-084, 3-085*, 3-086*, 3-087˜3-089, 3-090*, 3-091*, 3-092*, 3-093*, 3-094˜3-098, 3-100*, 3-102˜3-104, 3-105*, 3-106˜3-108, 3-109*, 3-110*, 3-111*, 3-112*, 3-113*, 3-114, 3-115, 3-116*, 3-117, 3-119˜3-127, 3-129, 3-131, 3-132*, 3-133˜3-136, 3-138˜3-141, 3-143, 3-146, 3-148, 3-150, 3-151**, 4-002, 4-003*, 4-004*, 4-005, 4-006*, 4-008˜4-010, 5-001*, 5-002*, 5-003*, 5-004*, 5-005*, 5-006, 5-007, 5-008*, 5-009*, 5-010*, 5-011*, 5-012*, 5-013*, 5-014*, 5-015*, 5-016, 5-017, 5-019, 5-022*, 5-023*, 5-029*, 5-030˜5-035, 5-036*, 5-037*, 5-038*, 5-039*, 5-040*, 5-041*, 5-042, 5-043, 5-044*, 5-045*, 5-046*, 5-047*, 5-048*, 5-049*, 5-050*, 5-051*, 5-052*, 5-053*, 5-054˜5-056, 5-057*, 5-058*, 5-059*, 5-060*, 5-061*, 5-062*, 5-063*, 5-064*, 5-065*, 5-066, 5-067*, 5-068*, 5-069*, 5-070*, 5-071*, 5-072*, 5-073*, 5-074*, 5-075, 5-075(+)*, 5-075(−), 5-076*, 5-077*, 5-078*, 5-079˜5-082, 5-083*, 5-084, 5-085*, 5-086*, 5-087*, 5-088*, 5-089*, 5-090**, 5-091*, 5-092*, 5-093*, 5-094*, 5-095, 5-097, 5-098, 5-099*, 5-100*, 5-101*, 5-102*, 5-103*, 5-104*, 5-105*, 5-106˜5-108, 5-109*, 5-110, 5-111*, 5-112*, 5-113*, 5-114*, 5-115, 5-116, 5-117*, 5-118*, 5-119*, 5-120**, 5-121*, 5-122*, 5-123*, 5-124**, 5-125, 5-126*, 5-127, 5-128*, 5-129, 5-130*, 5-131˜5-133, 5-134*, 5-135˜5-137, 5-138*, 5-139*, 5-140*, 5-141*, 5-142*, 5-143, 5-144*, 5-145*, 5-146, 5-147*, 5-148*, 5-149, 5-150, 5-151*, 5-151(+)*, 5-151(−), 5-152˜5-155, 5-156*, 5-158, 5-159, 5-160*, 5-161**, 5-162*, 5-163, 5-164, 5-165*, 5-166*, 5-167, 5-168**, 5-169*, 5-170˜5-172, 5-173**, 5-174**, 5-175, 5-176*, 5-177, 5-178, 5-179*, 5-180*, 5-181*, 5-182*, 5-183*, 5-184, 5-185*, 5-186*, 5-187*, 5-188*, 5-189**, 5-189(+)*, 5-189(−), 5-190(+)*, 5-190(−), 5-191*, 5-192*, 5-193*, 5-194*, 5-195**, 5-196**, 5-197**, 5-198˜5-200, 5-201*, 5-202*, 5-203**, 5-204, 5-205*, 5-206*, 5-207, 5-208**, 5-209, 5-210*, 5-211*, 5-212*, 5-213*, 5-214*, 5-215*, 5-216*, 5-217**, 5-218*, 5-219*, 5-219(+)*, 5-219(−)*, 5-220*, 5-221*, 5-222*, 5-223*, 5-224*, 5-225*, 5-226*, 5-227*, 5-228*, 5-229*, 5-230*, 5-231*, 5-232*, 5-233*, 5-234*, 5-235**, 5-236*, 5-237, 5-238*, 5-239*, 5-240*, 5-241*, 5-242*, 5-243**, 5-244, 5-245*, 5-246*, 5-247*, 5-248, 5-249*, 5-250, 5-251*, 5-252, 5-253, 5-254*, 5-255, 5-256*, 5-257*, 5-258**, 5-259*, 5-260, 5-261*, 5-262**, 5-263**, 5-264*, 5-265*, 5-266, 5-267*, 5-268*, 5-270, 5-271, 5-272*, 5-273*, 5-274*, 5-275*, 5-276*, 5-277*, 5-278*, 5-279*, 5-280, 5-281, 5-282*, 5-283*, 5-284*, 5-285*, 5-286*, 5-287, 5-288*, 5-289*, 5-290, 5-291*, 5-292, 5-293, 5-294*, 5-295*, 5-296, 5-298, 5-299*, 5-300*, 5-301*, 5-302, 5-303*, 5-304, 5-305**, 5-306*, 5-307*, 5-308**, 5-309*, 5-310**, 5-311, 5-312*, 5-313*, 5-314*, 5-315*, 5-316, 5-317*, 5-318*, 5-319*, 5-320*, 5-321, 5-322, 5-323*, 5-324˜5-326, 5-328, 5-329*, 5-330*, 5-331*, 5-332*, 5-333*, 5-334*, 5-335*, 5-336*, 5-337, 5-338*, 5-339*, 5-340, 5-341, 5-342*, 5-343*, 5-344*, 5-345, 5-346*, 5-347, 5-349*, 5-350˜5-352, 5-353*, 5-354*, 5-355*, 5-356*, 5-357*, 5-358*, 5-359**, 5-360*, 5-361*, 5-362*, 5-363, 5-366, 5-372, 5-374*, 5-375*, 5-376**, 5-377**, 5-378*, 5-379**, 5-380**, 5-381**, 5-383*, 5-384*, 5-385**, 5-386**, 5-387*, 5-389*, 5-390*, 5-391, 5-392*, 5-393*, 5-395*, 5-396**, 5-397*, 5-398*, 5-399*, 5-400*, 5-401*, 5-402*, 5-403˜5-407, 5-408*, 5-409, 5-410*, 5-411*, 5-412*, 5-413*, 5-414, 5-415*, 5-416, 5-417*, 5-418*, 5-419*, 5-420*, 5-421*, 5-422*, 5-423*, 5-424*, 5-425*, 5-426*, 5-427*, 5-428*, 5-429*, 5-430*, 5-431, 5-432*, 5-433*, 5-434*, 5-436˜5-438, 5-439*, 5-440*, 5-441*, 5-442*, 5-443*, 5-444*, 5-445*, 5-446*, 5-447˜5-450, 5-452*, 5-453*, 5-454*, 5-455*, 5-456, 5-457, 5-458*, 5-459*, 5-460*, 5-461*, 5-462*, 5-463**, 5-464**, 5-465**, 5-466**, 5-467*, 5-468**, 5-469**, 5-470**, 5-471*, 5-472*, 5-473*, 5-474*, 5-475**, 5-476*, 5-477**, 5-478**, 5-479, 5-480*, 5-481˜5-486, 5-487**, 5-488**, 5-489*, 5-490˜5-493, 5-494**, 5-495**, 5-496**, 5-497**, 5-498**, 5-499**, 5-500*, 5-501˜5-505, 5-507, 5-508, 5-509**, 5-510**, 5-511**, 5-512*, 5-513*, 5-514*, 5-515*, 5-516*, 5-517*, 5-518, 5-519*, 5-520*, 5-521*, 5-522*, 5-523*, 5-524, 5-525, 5-526*, 5-527*, 5-528*, 5-529*, 5-530*, 5-531*, 5-532, 5-533*, 5-534, 5-535, 5-536*, 5-537*, 5-538*, 5-539*, 5-540, 5-540(+)*, 5-541*, 5-541(R), 5-541(S)*, 5-542, 5-543*, 5-544*, 5-545, 5-546*, 5-547*, 5-548*, 5-549*, 5-550, 5-551*, 5-552*, 5-553*, 5-554*, 5-555*, 5-556, 5-557*, 5-558*, 5-559˜5-565, 5-566*, 5-567, 5-568*, 5-569*, 5-570*, 5-571, 5-572*, 5-573*, 5-574*, 5-575*, 5-576*, 5-577*, 5-578*, 5-579*, 5-580*, 5-581*, 5-582*, 5-583*, 5-584*, 5-585*, 5-586*, 5-587*, 5-588*, 5-589*, 5-590*, 5-591, 5-592, 5-593*, 5-594*, 5-595*, 5-596*, 5-597*, 5-598*, 5-599*, 5-600*, 5-601*, 5-602, 5-603, 5-604*, 5-605**, 5-606**, 5-607*, 5-608**, 5-609, 5-610, 5-611*, 5-612**, 5-613**, 5-614*, 5-615*, 5-616*, 5-617*, 5-618, 5-619*, 5-620˜5-622, 5-623*, 5-624*, 5-625*, 5-626, 5-627**, 5-628**, 5-629*, 5-630*, 5-631*, 5-632*, 5-633*, 5-634*, 5-635*, 5-636, 5-637*, 5-638*, 5-639*, 5-640, 5-641*, 5-642**, 5-643*, 5-644**, 5-645*, 5-646*, 5-648*, 5-651, 5-653*, 5-654*, 5-655**, 5-656**, 5-657**, 5-658, 5-659*, 5-660**, 5-661*, 5-662**, 5-663, 5-664**, 5-665*, 5-666**, 5-667*, 5-668**, 5-669*, 5-670*, 5-671**, 5-672**, 5-674**, 5-676**, 5-678, 5-684**, 5-685**, 5-686**, 6-001*, 6-002, 6-003*, 6-004**, 6-005, 6-006**, 6-007*, 6-008*, 6-009, 6-010, 6-011*, 6-012, 6-013*, 6-015**, 6-016*, 6-017*, 6-018*, 6-019*, 6-020*, 6-021*, 6-022**, 6-023*, 6-024**, 6-025, 6-026*, 6-027*, 6-028*, 6-029*, 6-030, 6-031*, 6-032*, 6-033*, 6-034*, 6-035*, 6-036*, 6-037*, 6-038*, 6-039*, 6-040*, 6-041*, 6-042*, 6-043*, 6-044*, 6-045*, 6-046*, 6-047*, 6-048*, 6-049*, 6-050*, 6-051*, 6-052, 6-053, 6-054*, 6-055*, 6-056*, 6-057, 6-058*, 6-059*, 6-060**, 6-061, 6-062**, 6-063*, 6-064**, 6-065**, 6-066*, 6-067**, 6-071**, 6-074*, 6-075*, 6-076*, 6-077*, 6-078*, 6-079*, 6-080*, 6-080(+)*, 6-080(−)*, 6-082*, 6-083*, 6-084*, 6-085˜6-088, 6-089*, 6-090*, 6-091*, 6-092**, 6-093**, 6-094**, 6-095**, 6-096*, 6-097, 6-099, 6-100**, 6-101**, 6-102**, 6-103**, 6-104*, 6-105, 6-106*, 6-108, 6-109, 6-110*, 6-111*, 6-112*,6-113, 6-114*, 6-115*, 6-116, 6-117˜6-120, 6-121*, 6-122, 6-123*, 6-124*, 6-125**, 6-126*, 6-127, 6-129*, 6-130**, 6-131**, 6-132**, 6-133**, 7-001, 7-002*, 7-003*, 7-004*, 7-005*, 7-006*, 7-007*, 7-008*, 7-009*, 7-010*, 8-002*, 8-003*, 8-004, 8-005, 8-006*, 8-007*, 9-003, 9-008˜9-011, 10-001, 10-002*, 10-003˜10-005, 10-006*, 11-006, 11-018, 11-024, 11-025*, 11-026*, 11-038, 11-043, 11-045, 11-046, 11-049*, 11-050˜11-052, 11-054, 11-056, 11-058˜11-062, 11-066, 11-075, 11-088, 11-089, 11-098*, 11-099*, 11-101˜11-107, 11-108*, 11-109*, 11-110˜11-117, 11-119, 11-120*, 11-122, 11-124*, 11-125*, 11-128, 11-129, 11-132, 12-001, 12-002, 12-008.
    In the interim, the indication of “*” shows that the insecticidal test was carried out by use of a chemical solution of a concentration of 100 ppm, and the indication “**” shows that the insecticidal test was carried out by use of a chemical solution of a concentration of 10 ppm.
    • Test Example 2 Insecticidal Test Against Common Cutworm
  • A 10% emulsifiable concentrate (depending on the compounds, 10% wettable powder was applied for the test) of the compound of the present invention was diluted with water containing a spreading agent to prepare a chemical solution with a concentration of 500 ppm. To the chemical solution was dipped leaves of cabbage for about 10 seconds, and after air-drying, they were placed in a laboratory dish, then 5-common cutworm (Spodoptera litura) in the stage of second instar larva per the dish were released therein, and the dish was covered with a lid and contained at a thermostat chamber at 25° C. A number of dead insect(s) after 6 days was counted and a rate of dead insects was calculated by the calculation equation similar to that in Test Example 1. Incidentally, the test was carried out with two districts.
  • As a result, the following compounds showed an insecticidal rate of 80% or more among the compounds tested.
    The compounds of the present invention:
    No. 1-005, 1-015, 1-016, 1-057, 1-058, 1-062, 1-066, 1-069, 1-080, 1-081, 1-088, 1-101, 1-102, 1-105˜1-109, 1-118, 1-122, 1-123, 1-125, 1-127, 1-129, 1-130, 1-132, 1-153, 1-156, 1-157, 1-166˜1-168, 1-175, 1-176, 1-177*, 1-182˜1-184, 1-185*, 1-188*, 1-189*, 1-194, 1-206*, 1-207, 1-212, 1-214, 1-215, 1-225, 2-002, 2-003, 2-013, 2-019˜2-021, 2-022*, 2-024˜2-026, 2-028, 2-029, 2-031, 2-032, 2-034˜2-039, 2-041, 2-042, 2-044˜2-046, 2-047*, 2-048, 2-049, 2-050*, 2-051*, 2-052*, 2-054˜2-056, 2-057*, 2-058*, 2-059*, 2-061*, 2-062*, 2-064, 2-065*, 2-067*, 2-068*, 3-006, 3-018, 3-026, 3-030, 3-032˜3-035, 3-037, 3-043, 3-044, 3-047, 3-058, 3-060˜3-064, 3-068*, 3-069, 3-070*, 3-071*, 3-072, 3-078, 3-079, 3-081, 3-083˜3-086, 3-089, 3-090*, 3-091*, 3-093*, 3-094, 3-095, 3-098, 3-100*, 3-102, 3-103, 3-105*, 3-106, 3-107, 3-109, 3-110*, 3-111*, 3-112*, 3-113*, 3-114, 3-115, 3-116*, 3-117, 3-121, 3-123˜3-126, 3-129, 3-131, 3-132*, 3-135, 3-136, 3-139, 3-140, 3-145, 3-148, 3-150, 3-151**, 4-003*, 4-004, 4-006*, 4-010, 5-001*, 5-002*, 5-003*, 5-004*, 5-005*, 5-006, 5-007, 5-008*, 5-009*, 5-010, 5-011, 5-012*, 5-013*, 5-014*, 5-015*, 5-016, 5-017, 5-019, 5-022*, 5-023*, 5-029*, 5-032, 5-034, 5-035, 5-036*, 5-037*, 5-038*, 5-039*, 5-040*, 5-041*, 5-042, 5-045*, 5-046*, 5-047*, 5-048*, 5-049*, 5-050*, 5-051*, 5-052*, 5-053*, 5-054, 5-057*, 5-058*, 5-059*, 5-060˜5-064, 5-065*, 5-066˜5-068, 5-069*, 5-070*, 5-071*, 5-072*, 5-073˜5-075, 5-075(+)*, 5-076*, 5-077*, 5-078˜5-081, 5-083*, 5-084, 5-085, 5-086*, 5-087*, 5-088*, 5-089*, 5-090, 5-091*, 5-092*, 5-093*, 5-094*, 5-099˜5-101, 5-102*, 5-103*, 5-104*, 5-105*, 5-106, 5-109, 5-111*, 5-112, 5-113*, 5-114*, 5-115, 5-116, 5-117*, 5-118, 5-119*, 5-120, 5-121*, 5-122˜5-126, 5-128*, 5-130, 5-132˜5-134, 5-136, 5-137, 5-138*, 5-139*, 5-140˜5-147, 5-148*, 5-149, 5-151, 5-151(+)*, 5-152˜5-156, 5-159˜5-169, 5-171˜5-178, 5-179*, 5-180, 5-181, 5-182*, 5-183*, 5-184, 5-185*, 5-186*, 5-187*, 5-188*, 5-189, 5-189(+), 5-191*, 5-192*, 5-193˜5-201, 5-202*, 5-203, 5-204, 5-205*, 5-206*, 5-207˜5-209, 5-210*, 5-211*, 5-212*, 5-213*, 5-214*, 5-215*, 5-216*, 5-217, 5-218*, 5-219*, 5-219(+)*, 5-219(−), 5-220*, 5-221, 5-222*, 5-223*, 5-224*, 5-225, 5-226*, 5-227*, 5-228, 5-229, 5-230*, 5-231, 5-232*, 5-233*, 5-234*, 5-235, 5-236*, 5-237*, 5-239, 5-240*, 5-241*, 5-242*, 5-243˜5-245, 5-246*, 5-247*, 5-249*, 5-250, 5-251, 5-254*, 5-256*, 5-257˜5-259, 5-261*, 5-262, 5-263, 5-264*, 5-265*, 5-267, 5-268*, 5-269, 5-271, 5-272*, 5-273*, 5-274*, 5-275˜5-277, 5-278*, 5-279*, 5-280, 5-282*, 5-283*, 5-284, 5-285*, 5-286*, 5-288*, 5-289*, 5-291*, 5-292, 5-294*, 5-295*, 5-296, 5-298, 5-299*, 5-300, 5-301*, 5-302, 5-303, 5-305, 5-306*, 5-307*, 5-308˜5-311, 5-312*, 5-313*, 5-314*, 5-315*, 5-316, 5-317*, 5-318*, 5-319*, 5-320˜5-322, 5-323*, 5-329*, 5-330*, 5-331*, 5-332, 5-333*, 5-334*, 5-335˜5-337, 5-338*, 5-339*, 5-341, 5-342, 5-343*, 5-344*, 5-345, 5-346, 5-349*, 5-351, 5-353, 5-354, 5-355*, 5-356˜5-359, 5-360*, 5-361*, 5-362*, 5-363, 5-374*, 5-375*, 5-376, 5-377, 5-378*, 5-379˜5-386, 5-387*, 5-389*, 5-390*, 5-392*, 5-393*, 5-395, 5-396, 5-397*, 5-398*, 5-399*, 5-400*, 5-401*, 5-402*, 5-405˜5-407, 5-408*, 5-409, 5-410*, 5-411*, 5-412*, 5-413*, 5-415*, 5-417*, 5-418*, 5-419*, 5-420*, 5-421*, 5-422*, 5-423*, 5-424*, 5-425*, 5-426*, 5-427*, 5-428*, 5-429*, 5-430*, 5-432*, 5-433*, 5-434*, 5-437, 5-438, 5-439*, 5-440*, 5-441*, 5-442*, 5-443*, 5-444*, 5-446*, 5-447, 5-452*, 5-453*, 5-454*, 5-455*, 5-458*, 5-459*, 5-460*, 5-461*, 5-462*, 5-463**, 5-464**, 5-465**, 5-466**, 5-467*, 5-468**, 5-469**, 5-470**, 5-471*, 5-472*, 5-473*, 5-474*, 5-475**, 5-476*, 5-477**, 5-478**, 5-479, 5-480*, 5-481˜5-486, 5-487**, 5-488**, 5-489*, 5-490˜5-493, 5-494**, 5-495**, 5-496**, 5-497**, 5-498**, 5-499**, 5-500*, 5-501, 5-503, 5-505, 5-507, 5-508, 5-509**, 5-511**, 5-513*, 5-514*, 5-515*, 5-516*, 5-517*, 5-518, 5-519*, 5-520*, 5-521*, 5-522*, 5-523*, 5-526*, 5-527*, 5-528*, 5-529*, 5-530*, 5-531*, 5-532, 5-533*, 5-535, 5-536*, 5-537*, 5-538*, 5-539*, 5-540(+), 5-541*, 5-541(R), 5-541(S)*, 5-542, 5-543*, 5-545, 5-546, 5-548*, 5-549*, 5-551*, 5-552*, 5-553*, 5-554*, 5-555*, 5-556, 5-557*, 5-558*, 5-559, 5-560, 5-562, 5-565, 5-566*, 5-568*, 5-569*, 5-570*, 5-571, 5-572*, 5-573*, 5-574*, 5-575*, 5-576*, 5-577*, 5-578*, 5-579*, 5-580*, 5-581*, 5-582*, 5-583*, 5-584*, 5-585*, 5-586*, 5-587*, 5-588*, 5-589*, 5-590*, 5-592, 5-593*, 5-594*, 5-595*, 5-596*, 5-598*, 5-599*, 5-600*, 5-601*, 5-602, 5-603, 5-604*, 5-605**, 5-606**, 5-607*, 5-608**, 5-609, 5-610, 5-611*, 5-612**, 5-613**, 5-614*, 5-615*, 5-616*, 5-617*, 5-618, 5-619*, 5-621, 5-623*, 5-624*, 5-625*, 5-626, 5-627**, 5-628**, 5-629*, 5-630*, 5-631*, 5-632*, 5-633*, 5-634*, 5-635*, 5-636, 5-637*, 5-638*, 5-639*, 5-641*, 5-642**, 5-643*, 5-644**, 5-645*, 5-646*, 5-647*, 5-648*, 5-650, 5-651, 5-653*, 5-654*, 5-655**, 5-656**, 5-657**, 5-659*, 5-660**, 5-661*, 5-662**, 5-664**, 5-665*, 5-666**, 5-667*, 5-668**, 5-669*, 5-670*, 5-671**, 5-672**, 5-674**, 5-676**, 5-678, 5-684**, 5-685**, 5-686**, 6-001*, 6-002, 6-003*, 6-004˜6-006, 6-007*, 6-008*, 6-010, 6-012, 6-013, 6-015, 6-016, 6-017*, 6-018, 6-019*, 6-020*, 6-021*, 6-022˜6-025, 6-026*, 6-027*, 6-028˜6-030, 6-031*, 6-032*, 6-033*, 6-034*, 6-035*, 6-036˜6-038, 6-039*, 6-040, 6-041, 6-042*, 6-043*, 6-044, 6-045, 6-046*, 6-047*, 6-048*, 6-049*, 6-050*, 6-051*, 6-053, 6-054*, 6-055*, 6-056, 6-058˜6-067, 6-071, 6-074*, 6-075*, 6-076*, 6-077*, 6-078*, 6-079*, 6-080*, 6-080(+)*, 6-080(−)*, 6-082*, 6-083*, 6-084*, 6-086, 6-087, 6-089*, 6-090*, 6-091*, 6-092**, 6-093**, 6-094**, 6-095**, 6-096*, 6-098*, 6-099, 6-100**, 6-101**, 6-102**, 6-103**, 6-104*, 6-105, 6-106*, 6-110*, 6-111*, 6-112*, 6-114*, 6-120, 6-121*, 6-123*, 6-124*, 6-125**, 6-126*, 6-129*, 6-130**, 6-131**, 6-132**, 6-133**, 7-001, 7-002*, 7-003*, 7-004*, 7-005*, 7-006*, 7-007*, 7-008*, 7-009*, 7-010*, 8-002*, 8-003*, 8-004, 8-005, 8-006*, 8-007*, 9-009, 10-001˜10-005, 10-006*, 11-024, 11-025*, 11-026*, 11-038, 11-049*, 11-052, 11-055, 11-056, 11-061, 11-062, 11-066, 11-070, 11-098*, 11-099*, 11-108*, 11-109*, 11-119, 11-120*, 11-124*, 11-125*, 11-129, 12-001, 12-002, 12-008. In the interim, the indication of “*” shows that the insecticidal test was carried out by use of a chemical solution of a concentration of 100 ppm.
    • Test Example 3 Insecticidal Test Against Beet Armyworm
  • A 10% emulsifiable concentrate (depending on the compounds, 10% wettable powder was applied for the test) of the compound of the present invention was diluted with water containing a spreading agent to prepare a chemical solution with a concentration of 100 ppm. To the chemical solution was dipped leaves of cabbage for about 10 seconds, and after air-drying, they were placed in a laboratory dish, then 5-beet armyworm (Spodoptera exigua) in the stage of second instar larva per the dish were released therein, and the dish was covered with a lid and contained at a thermostat chamber at 25° C. A number of dead insect(s) after 6 days was counted and a rate of dead insects was calculated by the calculation equation similar to that in Test Example 1. Incidentally, the test was carried out with two districts.
  • As a result, the following compounds showed an insecticidal rate of 80% or more among the compounds tested.
    The compounds of the present invention: No. 1-015, 1-016, 1-057, 1-058, 1-062˜1-064, 1-066, 1-080, 1-081, 1-088, 1-102, 1-105, 1-106, 1-109, 1-118, 1-122, 1-123, 1-125, 1-127, 1-151, 1-153, 1-155˜1-157, 1-166, 1-175, 1-189, 1-207, 1-214, 1-215, 2-003, 2-019, 2-020, 3-026, 3-027, 3-030, 3-032, 3-037, 3-060, 3-091, 3-093, 3-095, 3-109, 3-110, 3-112, 3-125, 5-001˜5-005, 5-008, 5-009, 5-029, 5-036, 5-037, 5-040, 5-041, 5-045, 5-046, 5-048, 5-049, 5-050, 5-052, 5-053, 5-057˜5-059, 5-061˜5-065, 5-067˜5-069, 5-071, 5-073˜5-075, 5-075(+), 5-076, 5-083, 5-086˜5-089, 5-091, 5-092, 5-094, 5-111, 5-113, 5-117˜5˜119, 5-122, 5-138˜5-142, 5-147, 5-148, 5-151, 5-160, 5-165, 5-174, 5-182, 5-183, 5-185˜5-188, 5-189(+), 5-202, 5-205, 5-210˜5˜212, 5-214˜5-216, 5-218, 5-219, 5-219(+), 5-220, 5-223, 5-226, 5-227, 5-230, 5-232˜5-234, 5-236, 5-239, 5-241, 5-247, 5-251, 5-257, 5-261, 5-264, 5-268, 5-273˜5-275, 5-279, 5-282, 5-283, 5-285, 5-286, 5-288, 5-291, 5-294, 5-295, 5-301, 5-306, 5-307, 5-309, 5-310, 5-312˜5-315, 5-320, 5-321, 5-323, 5-331˜5-334, 5-339, 5-341, 5-355˜5-357, 5-360˜5-362, 5-374, 5-375, 5-378, 5-387, 5-389, 5-390, 5-397, 5-398, 5-412, 5-429, 5-433, 5-440, 5-474, 5-476, 5-478, 5-480, 5-488, 5-494, 5-495, 5-588, 5-604, 5-638, 5-642, 6-017˜6-021, 6-026, 6-027, 6-031, 6-033˜6-041, 6-043˜6-045, 6-048, 6-049, 6-058, 6-059, 6-063˜6-066, 6-074˜6-076, 6-095, 6-131, 7-002, 7-003, 7-005˜7-009, 8-002, 11-024, 11-025, 11-026.
    • Test Example 4 Insecticidal Test Against Oriental Tea Tortx
  • A 10% emulsifiable concentrate (depending on the compounds, 10% wettable powder was applied for the test) of the compound of the present invention was diluted with water containing a spreading agent to prepare a chemical solution with a concentration of 100 ppm. To the chemical solution was dipped leaves of cabbage for about 10 seconds, and after air-drying, they were placed in a laboratory dish, then 5-oriental tea tortix (Homona magnanima) in the stage of second instar larva per the dish were released therein, and the dish was covered with a lid and contained at a thermostat chamber at 25° C. A number of dead insect(s) after 6 days was counted and a rate of dead insects was calculated by the calculation equation similar to that in Test Example 1. Incidentally, the test was carried out with two districts.
  • As a result, the following compounds showed an insecticidal rate of 80% or more among the compounds tested.
    The compounds of the present invention: No. 1-015, 1-016, 1-057, 1-058, 1-062, 1-080, 1-105, 1-107, 1-0122, 1-123, 1-125, 1-127, 1-153, 1-156, 1-189, 1-207, 1-214, 1-215, 2-003, 2-034, 2-035, 2-051, 2-052, 3-037, 3-060, 3-095, 3-110, 3-112, 3-125, 3-129, 4-003, 5-001, 5-003˜5-005, 5-008, 5-009, 5-012, 5-013, 5-022, 5-029, 5-037, 5-040, 5-041, 5-045˜5-050, 5-052, 5-053, 5-057˜5-059, 5-061˜5-065, 5-069˜5-071, 5-073, 5-075, 5-075(+), 5-076, 5-077, 5-083, 5-086˜5-090, 5-092˜5-094, 5-102, 5-103, 5-111, 5-113, 5-114, 5-117, 5-119, 5-121, 5-122, 5-138˜5-142, 5-147, 5-148, 5-151, 5-151(+), 5-156, 5-160, 5-161, 5-165, 5-166, 5-180, 5-182, 5-183, 5-185, 5-187, 5-188, 5-189(+), 5-202, 5-205, 5-208, 5-210˜5-212, 5-214˜5-216, 5-218, 5-219, 5-219(+), 5-220, 5-221, 5-223, 5-226˜5-228, 5-230, 5-232˜5-234, 5-236, 5-240˜5-242, 5-246, 5-247, 5-251, 5-254, 5-273˜5-275, 5-279, 5-282, 5-283, 5-285, 5-286, 5-288, 5-289, 5-291, 5-294, 5-295, 5-301, 5-306, 5-307, 5-310, 5-312, 5-313, 5-315, 5-319, 5-321, 5-323, 5-329, 5-330, 5-338, 5-339, 5-341, 5-356, 5-357, 5-359, 5-360, 5-362, 5-374, 5-375, 5-378, 5-379, 5-381, 5-387˜5-390, 5-392, 5-393, 5-395˜5-399, 5-401, 5-412, 5-418, 5-419, 5-426, 5-429, 5-430, 5-433, 5-434, 5-441, 5-458˜5-461, 5-463˜5-465, 5-468, 5-470, 5-472, 5-474, 5-476˜5-478, 5-480, 5-488, 5-494, 5-515, 5-519, 5-523, 5-539, 5-541, 5-541(S), 5-553, 5-554, 5-576, 5-579, 5-585, 5-588, 5-594, 5-601, 5-604, 5-606, 5-612, 5-617, 5-638, 5-642, 5-655, 5-656, 6-001, 6-003, 6-017, 6-018, 6-020, 6-021, 6-027, 6-031, 6-033˜6-035, 6-038˜6-041, 6-043, 6-066, 6-075, 6-076, 6-081, 6-093, 6-095, 6-124, 6-131, 7-002˜7-009, 8-002, 11-024, 11-026.
    • Test Example 5 Insecticidal Test Against Corn Earworm
  • A 10% emulsifiable concentrate (depending on the compounds, 10% wettable powder was applied for the test) of the compound of the present invention was diluted with water containing a spreading agent to prepare a chemical solution with a concentration of 100 ppm. To the chemical solution was dipped leaves of cabbage for about 10 seconds, and after air-drying, they were placed in a laboratory dish, then 1-corn earworm (Helicoverpa armigera) in the stage of second instar larva per the dish were released therein, and the dish was covered with a lid and contained at a thermostat chamber at 25° C. A number of dead insect(s) after 6 days was counted and a rate of dead insects was calculated by the calculation equation similar to that in Test Example 1. Incidentally, the test was carried out with twelve districts.
  • As a result, the following compounds showed an insecticidal rate of 80% or more among the compounds tested.
    The compounds of the present invention: No. 1-066, 1-153, 1-156, 1-207, 1-214, 1-215, 2-034, 2-035, 2-042, 2-055, 2-057, 2-059, 2-062, 2-063, 2-067, 2-068, 3-027, 3-030, 3-032, 3-086, 3-095, 3-109, 3-110, 3-112, 3-151, 5-008, 5-009, 5-022, 5-040, 5-046, 5-047, 5-049, 5-050, 5-052, 5-053, 5-057˜5-059, 5-061˜5-063, 5-065, 5-068, 5-070, 5-071, 5-075, 5-075(+), 5-076, 5-077, 5-083, 5-086˜5-089, 5-099˜5-101, 5-109, 5-113, 5-117, 5-120˜5-122, 5-126, 5-138, 5-139, 5-141, 5-142, 5-147, 5-148, 5-151, 5-151 (+), 5-156, 5-160, 5-165, 5-169, 5-177, 5-180, 5-185, 5-189(+), 5-193, 5-208, 5-210˜5-212, 5-214˜5-219, 5-219(+), 5-223, 5-227, 5-228, 5-230, 5-231, 5-233, 5-234, 5-236, 5-241, 5-245, 5-246, 5-249, 5-251, 5-254, 5-261, 5-264, 5-269, 5-273˜5-275, 5-279, 5-284, 5-286, 5-291, 5-294, 5-295, 5-306, 5-307, 5-309, 5-310, 5-312˜5-315, 5-319, 5-323, 5-331˜5-336, 5-338, 5-339, 5-341, 5-353˜5-355, 5-357, 5-359, 5-360, 5-374, 5-375, 5-378˜5-381, 5-383, 5-384, 5-387, 5-389, 5-390, 5-393, 5-395, 5-397˜5-400, 5-408˜5-413, 5-415, 5-420˜5-424, 5-426, 5-427, 5-429, 5-433, 5-434, 5-440, 5-443, 5-446, 5-452˜5-454, 5-458˜5-470, 5-473˜5-481, 5-483, 5-484, 5-487˜5-489, 5-494˜5-499, 5-508˜5-511, 5-513, 5-515˜5-517, 5-519, 5-522, 5-523, 5-526˜5-529, 5-531˜5-533, 5-538, 5-539, 5-541, 5-541 (S), 5-543, 5-548, 5-549, 5-558˜5-560, 5-566, 5-568, 5-570, 5-572˜5-577, 5-579˜5-589, 5-595, 5-599˜5-601, 5-604, 5-606˜5-608, 5-611, 5-612, 5-614˜5-619, 5-623˜5-625, 5-627˜5-639, 5-641˜5-646, 5-654˜5-657, 5-660˜5-662, 5-664˜5-668, 5-671, 5-672, 5-674, 5-676, 5-684, 5-685, 6-003, 6-004, 6-016˜6-019, 6-021, 6-023, 6-024, 6-026, 6-027, 6-031, 6-033˜6-041, 6-043˜6-045, 6-048, 6-049, 6-056, 6-066, 6-074˜6-080, 6-080(+), 6-080(−), 6-081˜6-084, 6-091˜6-095, 6-098, 6-100, 6-102˜6-106, 6-110, 6-111, 6-124, 6-126, 6-130˜6-132, 7-002˜7-009, 8-002, 8-005˜8-007, 10-006, 11-024, 11-125, 11-130.
    • Test Example 6 Insecticidal Test Against Peach Fruit Moth
  • A 10% emulsifiable concentrate (depending on the compounds, 10% wettable powder was applied for the test) of the compound of the present invention was diluted with water containing a spreading agent to prepare a chemical solution with a concentration of 100 ppm. To the chemical solution was dipped apple young fruits on which peach fruit moth (Carpocina sasakii) laid eggs (20-egg/fruit) for about 10 seconds, and after air-drying, they were placed in a laboratory dish, and the dish was covered with a lid and contained at a thermostat chamber at 25° C. A number of dead insect(s) after 20 days was counted and a rate of dead insects was calculated by the calculation equation similar to that in Test Example 1. Incidentally, the test was carried out with two districts.
  • As a result, the following compounds showed an insecticidal rate of 80% or more among the compounds tested.
    The compounds of the present invention: No. 5-049, 5-050, 5-070, 5-076, 5-083, 5-088, 5-111, 5-148, 5-219, 5-219(+), 5-221, 5-234, 5-286, 5-291, 5-323, 5-360, 5-387, 5-390, 5-398, 5-480, 5-494, 6-027, 6-039, 7-008.
    • Test Example 7 Insecticidal Test Against Frankliniella occidentalis
  • A wet filter paper was laid in a styrol cup having an inner diameter of 7 cm, a leaf of a common bean cut out so as to have the same diameter was laid thereon, and 10-Frankliniella occidentalis with first instar larva per leaf was inoculated thereon. A 10% emulsifiable concentrate (depending on the compounds, 10% wettable powder was applied for the test) of the compound of the present invention was diluted with water containing a spreading agent to prepare a chemical solution with a concentration of 500 ppm. The chemical solution was sprayed with a rotating spray tower in an amount of 2.5 ml per styrol cup, and the styrol cups were covered with lids and contained at a thermostat chamber at 25° C. A number of dead insect(s) after 2 days was counted and a rate of dead insects was calculated by the calculation equation similar to that in Test Example 1. Incidentally, the test was carried out with two districts.
  • As a result, the following compounds showed an insecticidal rate of 80% or more among the compounds tested.
    The compounds of the present invention: No. 1-175, 1-177˜1-179, 1-182, 2-020, 2-022, 2-028*, 2-029*, 2-032, 2-033, 2-034*, 2-035*, 2-037*, 2-038*, 2-039*, 2-040*, 2-041*, 2-042*, 2-043*, 2-044*, 2-045*, 2-046*, 2-047, 2-048*, 2-049*, 2-050˜2-052, 2-057˜2-068, 3-068, 3-072*, 3-080, 3-084˜3-086, 3-090, 3-093, 3-105, 3-107, 3-109, 3-110, 3-112, 3-114, 3-122˜3-125, 3-132, 3-135, 3-136, 3-151, 4-004, 4-006, 5-001, 5-003, 5-009, 5-013, 5-022, 5-023, 5-029, 5-037˜5-041, 5-044˜5-053, 5-057˜5-075, 5-075(+), 5-076˜5-078, 5-081˜5-089, 5-090*, 5-091˜5-094, 5-099˜5-105, 5-109, 5-111˜5-119, 5-120*, 5-121˜5-123, 5-124*, 5-126˜5-128, 5-129*, 5-130, 5-131*, 5-134, 5-137˜5-142, 5-143*, 5-144, 5-145, 5-146*, 5-147, 5-148, 5-150, 5-151, 5-151(+), 5-153*, 5-154, 5-156, 5-158˜5-160, 5-161*, 5-162, 5-164˜5-166, 5-167*, 5-168*, 5-169, 5-171, 5-172*, 5-178˜5-188, 5-189(+), 5-190(+), 5-191˜5-194, 5-201, 5-202, 5-205˜5-207, 5-208*, 5-210˜5˜216, 5-217*, 5-218, 5-219, 5-219(+), 5-219(−), 5-220˜5-234, 5-236˜5-242, 5-244˜5-247, 5-249, 5-251˜5-254, 5-255*, 5-256, 5-257, 5-258*, 5-259˜5-261, 5-264, 5-265, 5-269*, 5-270, 5-271*, 5-272˜5-283, 5-284˜5-289, 5-291, 5-292, 5-294, 5-295, 5-297, 5-299, 5-300, 5-301, 5-302*, 5-303, 5-306, 5-307, 5-309, 5-310*, 5-311˜5-315, 5-318, 5-319, 5-321˜5-323, 5-329˜5-336, 5-338, 5-339, 5-341˜5-346, 5-348, 5-349, 5-353˜5-358, 5-360˜5-362, 5-374, 5-375, 5-378, 5-379*, 5-380*, 5-381*, 5-383, 5-384, 5-385*, 5-387˜5-393, 5-395, 5-396*, 5-397˜5-401, 5-403˜5-406, 5-408˜5-413, 5-415, 5-417˜5-430, 5-432˜5-434, 5-439˜5-443, 5-445, 5-446, 5-449, 5-452, 5-453, 5-455, 5-458˜5-503, 5-507˜5-512, 5-514˜5-516, 5-518, 5-519, 5-521˜5-525, 5-527˜5-534, 5-537˜5-539, 5-541, 5-541(S), 5-542, 5-543, 5-545˜5-549, 5-550˜5-562, 5-564, 5-565, 5-567˜5-576, 5-579˜5-590, 5-592, 5-599˜5-601, 5-604˜5-609, 5-611, 5-612, 5-614˜5-619, 5-621, 5-623, 5-624, 5-626˜5-639, 5-641˜5-648, 5-650, 5-651, 5-653˜5-672, 5-674, 5-676, 5-678, 5-684˜5-686, 6-001˜6-003, 6-004*, 6-005*, 6-006*, 6-007˜6-013, 6-015*, 6-016˜6-021, 6-022*, 6-023, 6-024*, 6-025*, 6-026˜6-050, 6-054˜6-056, 6-058, 6-059, 6-063, 6-066, 6-070, 6-071*, 6-074˜6-080, 6-080(+), 6-080(−), 6-081˜6-086, 6-089˜6-111, 6-113˜6-115, 6-117, 6-119˜6-124, 6-126, 6-127, 6-129˜6-133, 7-001, 7-003˜7-010, 8-002, 8-003, 8-005, 8-006, 10-002, 10-005, 10-006, 11-024˜11-026, 11-043, 11-045, 11-054˜11-056, 11-059, 11-070, 11-089, 11-099, 11-107, 11-114, 11-120, 11-125, 11-128˜11-130, 11-132, 12-002, 12-007, 12-008.
    In the interim, the indication of “*” shows that the insecticidal test was carried out by use of a chemical solution of a concentration of 100 ppm.
    • Test Example 8 Insecticidal Test Against Thrips palmi
  • A wet filter paper was laid in a styrol cup having an inner diameter of 7 cm, a leaf of a common bean cut out so as to have the same diameter was laid thereon, and 10-Thrips palmi in the stage of adult per leaf was inoculated thereon. A 10% emulsifiable concentrate (depending on the compounds, 10% wettable powder was applied for the test) of the compound of the present invention was diluted with water containing a spreading agent to prepare a chemical solution with a concentration of 100 ppm. The chemical solution was sprayed with a rotating spray tower in an amount of 2.5 ml per styrol cup, and the styrol cups were covered with lids and contained at a thermostat chamber at 25° C. A number of dead insect(s) after 2 days was counted and a rate of dead insects was calculated by the calculation equation similar to that in Test Example 1. Incidentally, the test was carried out with two districts.
  • As a result, the following compounds showed an insecticidal rate of 80% or more among the compounds tested.
    The compounds of the present invention: No. 1-179, 1-196, 2-022, 2-024˜2-026, 2-028, 2-029, 2-033, 2-035, 2-039, 2-044˜2-048, 2-050˜2-052, 2-057˜2-059, 2-061, 2-063, 2-065, 2-067, 3-079, 3-085, 3-086, 3-091, 3-110, 3-112, 3-124, 3-131, 3-148, 3-151, 4-003˜4-005, 4-010, 5-001, 5-003, 5-006, 5-008, 5-012˜5-015, 5-022, 5-023, 5-029, 5-036, 5-037, 5-040, 5-045˜5-053, 5-057˜5-063, 5-065, 5-067, 5-068, 5-070˜5-075, 5-075(+), 5-076˜5-079, 5-081˜5-084, 5-086˜5-093, 5-099, 5-102˜5-104, 5-111˜5-114, 5-117˜5-121, 5-124, 5-128˜5-130, 5-137˜5-148, 5-151, 5-151(+), 5-153, 5-156, 5-160˜5-162, 5-165, 5-166, 5-179, 5-180, 5-182˜5-186, 5-188, 5-189(+), 5-193, 5-202, 5-205, 5-206, 5-208˜5-210, 5-214˜5-216, 5-218, 5-219, 5-219 (+), 5-220, 5-224˜5-226, 5-228˜5-230, 5-232˜5-234, 5-236, 5-238, 5-239, 5-242, 5-246, 5-247, 5-251, 5-256˜5-258, 5-261, 5-264, 5-269, 5-273˜5-276, 5-278, 5-279, 5-280, 5-282, 5-283, 5-285, 5-286, 5-288, 5-289, 5-291, 5-294, 5-295, 5-299, 5-303, 5-306, 5-309, 5-310, 5-312˜5-314, 5-319, 5-322, 5-323, 5-329, 5-330, 5-332, 5-334, 5-335, 5-338, 5-339, 5-346, 5-349, 5-353˜5-362, 5-374, 5-375, 5-378˜5-381, 5-383˜5-385, 5-387, 5-389, 5-390, 5-395˜5-401, 5-408˜5-413, 5-415, 5-418˜5-424, 5-426, 5-427, 5-429, 5-430, 5-432˜5-434, 5-439˜5-443, 5-446, 5-452˜5-455, 5-458˜5-470, 5-471˜5-492, 5-494˜5-501, 5-508˜5-513, 5-515, 5-516, 5-519, 5-521˜5-523, 5-525, 5-527˜5-531, 5-533, 5-536, 5-538, 5-539, 5-541, 5-541(S), 5-543, 5-547, 5-549, 5-553˜5-555, 5-560, 5-564, 5-568˜5-570, 5-572˜5-576, 5-579, 5-581, 5-582, 5-584˜5-590, 5-593, 5-598˜5-601, 5-604˜5-609, 5-611˜5-613, 5-616˜5-619, 5-621, 5-623˜5-625, 5-627˜5-639, 5-641˜5-648, 5-650, 5-651, 5-655˜5-657, 5-659˜5-662, 5-664˜5-669, 5-672, 5-674, 5-676, 5-684, 5-685, 6-001, 6-003˜6-008, 6-015, 6-017˜6-024, 6-026˜6-035, 6-037˜6-041, 6-043˜6-045, 6-047˜6-049, 6-054˜6-056, 6-058, 6-059, 6-063, 6-066, 6-070, 6-073˜6-080, 6-080(46-080(−), 6-081˜6-084, 6-089, 6-090, 6-092˜6-096, 6-098˜6-107, 6-109˜6-111, 6-114, 6-115, 6-120, 6-121, 6-123, 6-124, 6-130˜6-133, 7-003, 7-005˜7-009, 8-002, 8-006, 8-007, 9-011, 10-002, 10-006, 11-025, 11-026, 11-054, 11-056, 11-059, 11-125, 11-129, 12-002, 12-008.
    • Test Example 9 Insecticidal Test Against Eysarcoris lewisi
  • A 10% emulsifiable concentrate (depending on the compounds, 10% wettable powder was applied for the test) of the compound of the present invention was diluted with water containing a spreading agent to prepare a chemical solution with a concentration of 500 ppm. To the chemical solution was dipped leave sheaths of rice for about 10 seconds, and after air-drying, they were placed in a test tube, then 5-Eysarcoris lewisi in the stage of first instar larva per the test tube were released therein, and the test tube was covered with a sponge and contained at a thermostat chamber at 25° C. A number of dead insect(s) after 2 days was counted and a rate of dead insects was calculated by the calculation equation similar to that in Test Example 1. Incidentally, the test was carried out with two districts.
  • As a result, the following compounds showed an insecticidal rate of 80% or more among the compounds tested.
    The compounds of the present invention:
    No. 1-015, 1-050, 1-051, 1-175, 1-209, 2-029, 2-034, 2-035, 2-042, 2-044˜2-052, 2-054, 2-055, 2-057˜2-059, 2-061, 2-062, 2-065, 2-067, 2-068, 3-047, 3-068, 3-070˜3-072, 3-086, 3-090, 3-093, 3-106, 3-109˜3-112, 3-114, 3-125, 3-131, 3-151, 5-001, 5-003, 5-005, 5-008, 5-009, 5-013˜5-015, 5-017, 5-022, 5-023, 5-026, 5-029, 5-037˜5-041, 5-045˜5-053, 5-058˜5-065, 5-067˜5-069, 5-071˜5-075, 5-075(+), 5-076˜5-078, 5-081, 5-083, 5-084˜5-094, 5-099˜5-105, 5-111˜5˜114, 5-116˜5-122, 5-124, 5-126, 5-128, 5-130, 5-134, 5-137˜5-142, 5-144, 5-145, 5-147, 5-148, 5-150, 5-151, 5-151(+), 5-154, 5-156, 5-158˜5-162, 5-165, 5-166, 5-168, 5-169, 5-171, 5-173, 5-174, 5-179˜5-189, 5-189(+), 5-191, 5-195˜5-197, 5-203, 5-205, 5-206, 5-208˜5-210, 5-212˜5-216, 5-218, 5-219, 5-219(+), 5-220˜5-230, 5-232, 5-233, 5-235, 5-236, 5-238˜5-247, 5-249, 5-251, 5-254, 5-256˜5-262, 5-264, 5-265, 5-273˜5-279, 5-283, 5-285, 5-286, 5-288, 5-289, 5-291, 5-294, 5-295, 5-299˜5-301, 5-304˜5-310, 5-312˜5-315, 5-318˜5-321, 5-323, 5-329, 5-330, 5-332, 5-334, 5-335, 5-338, 5-339, 5-341˜5-344, 5-346, 5-348, 5-353˜5-360, 5-362, 5-374˜5-387, 5-389, 5-390, 5-392, 5-393, 5-395˜5-401, 5-403˜5-405, 5-408˜5-413, 5-415, 5-417˜5-424, 5-426˜5-429, 5-431˜5-434, 5-440, 5-443, 5-445, 5-446, 5-448, 5-452˜5-455, 5-457˜5-465, 5-467˜5-470, 5-472˜5-478, 5-480, 5-487˜5-489, 5-491, 5-492, 5-494˜5-500, 5-505, 5-509, 5-510, 5-512, 5-515˜5-517, 5-519˜5-523, 5-526˜5-533, 5-537˜5-539, 5-541, 5-541(S), 5-543, 5-546, 5-547, 5-549, 5-551˜5-558, 5-562, 5-568˜5-570, 5-572˜5-577, 5-579, 5-582˜5-588, 5-593, 5-595, 5-598, 5-600, 5-601, 5-604, 5-606, 5-611, 5-612, 5-614˜5-617, 5-619, 5-621, 5-623, 5-627, 5-631, 5-635˜5-638, 5-642, 5-643, 5-646, 5-648, 5-654˜5-657, 5-660, 5-661, 5-664, 5-668, 5-670, 5-672, 5-674, 5-684˜5-686, 6-001, 6-006˜6-013, 6-015˜6-024, 6-026˜6-029, 6-031˜6-051, 6-054˜6-056, 6-058˜6-060, 6-062˜6-067, 6-070, 6-071, 6-074˜6-080, 6-080(+), 6-080(−), 6-081˜6-086, 6-089˜6-093, 6-095, 6-098˜6-103, 6-110˜6-112, 6-114˜6-118, 6-121, 6-124, 6-129˜6-132, 7-002˜7-010, 10-006, 11-060, 11-098, 11-125.
    • Test Example 10 Insecticidal Test Against Brown Rice Planthopper
  • A 10% emulsifiable concentrate (depending on the compounds, 10% wettable powder was applied for the test) of the compound of the present invention was diluted with water containing a spreading agent to prepare a chemical solution with a concentration of 500 ppm. To the chemical solution was dipped leave sheaths of rice for about 10 seconds, and after air-drying, they were placed in a test tube, then 5-brown rice planthopper (Nilaparvata lugens) in the second instar larva per the test tube were released therein, and the test tube was covered with a sponge and contained at a thermostat chamber at 25° C. A number of dead insect(s) after 6 days was counted and a rate of dead insects was calculated by the calculation equation similar to that in Test Example 1. Incidentally, the test was carried out with two districts.
  • As a result, the following compounds showed an insecticidal rate of 80% or more among the compounds tested.
    The compounds of the present invention: No. 1-005˜1-007, 1-017, 1-061, 1-154, 1-175, 1-185, 1-188, 1-189, 2-018, 2-020, 2-025˜2-027, 2-029, 2-033, 2-034, 2-036, 2-044, 2-046, 2-051, 2-052, 2-054, 2-057˜2-059, 2-062, 2-065, 2-068, 3-013, 3-068, 3-070, 3-072, 3-075, 3-109, 3-112, 3-125, 3-151, 5-001, 5-003, 5-009, 5-013, 5-015, 5-023, 5-029, 5-040, 5-041, 5-049, 5-050, 5-053, 5-058, 5-060, 5-061, 5-063, 5-065˜5-068, 5-070˜5-074, 5-075(+), 5-076, 5-077, 5-080, 5-081, 5-083, 5-084, 5-086˜5-088, 5-090˜5-094, 5-099, 5-102, 5-106, 5-111, 5-113, 5-117˜5-120, 5-130, 5-138˜5-148, 5-151, 5-151(+), 5-152˜5-156, 5-160, 5-161, 5-163, 5-170, 5-173, 5-174, 5-182, 5-186, 5-189, 5-189(+), 5-195, 5-197, 5-203, 5-205, 5-208, 5-210, 5-212, 5-214, 5-216, 5-219, 5-219(+), 5-220, 5-226, 5-230˜5-232, 5-234˜5-236, 5-239, 5-240, 5-242, 5-243, 5-245, 5-246, 5-251, 5-254, 5-257, 5-258, 5-261, 5-262, 5-264, 5-265, 5-273˜5-275, 5-279, 5-280, 5-285, 5-286, 5-288, 5-294, 5-295, 5-305˜5-310, 5-313, 5-315, 5-323, 5-330, 5-335, 5-339, 5-341, 5-344, 5-353˜5-360, 5-374˜5-377, 5-379˜5-388, 5-390, 5-392, 5-393, 5-396, 5-398˜5-401, 5-405, 5-410, 5-412, 5-413, 5-419, 5-421˜5-423, 5-426, 5-427, 5-429, 5-432, 5-433, 5-440, 5-453, 5-455, 5-460, 5-461, 5-463˜5-465, 5-467, 5-470, 5-472˜5-476, 5-482, 5-483, 5-487, 5-490˜5-492, 5-494˜5-496, 5-498, 5-499, 5-501, 5-510˜5-512, 5-515, 5-519, 5-521, 5-523, 5-525, 5-527˜5-530, 5-532, 5-537˜5-539, 5-541, 5-541 (S), 5-546, 5-547, 5-550˜5-554, 5-560, 5-568, 5-570, 5-572˜5-576, 5-579, 5-583, 5-585, 5-586, 5-588, 5-608, 5-614, 5-617, 5-619, 5-621, 5-627, 5-628, 5-636, 5-637, 5-642, 5-646, 5-648, 5-651, 5-654, 5-656, 5-657, 5-660, 5-662, 5-664, 5-670, 5-672, 5-674, 5-684, 5-686, 6-001, 6-003, 6-007, 6-015˜6-023, 6-027˜6-045, 6-048˜6-050, 6-056, 6-058˜6-065, 6-076˜6-080, 6-080(+), 6-080(−), 6-081˜6-083, 6-086, 6-090˜6-093, 6-096, 6-098, 6-100˜6-103, 6-105, 6-114, 6-115, 6-117, 6-124, 6-125, 6-130˜6-132, 7-001˜7-004, 7-006, 7-008, 7-009, 8-003, 9-009, 11-039, 11-041, 11-054, 11-098, 11-101, 11-132.
    • Test Example 11 Insecticidal Test Against Bemisia argentifolii
  • A wet filter paper was laid in a styrol cup having an inner diameter of 7 cm, a leaf of a tomato cut out on which Bemisia argentifolii laid eggs (10-egg/leaf) was laid thereon. A 10% emulsifiable concentrate (depending on the compounds, 10% wettable powder was applied for the test) of the compound of the present invention was diluted with water containing a spreading agent to prepare a chemical solution with a concentration of 500 ppm. The chemical solution was sprayed with a rotating spray tower in an amount of 2.5 ml per styrol cup, and the styrol cups were covered with lids and contained at a thermostat chamber at 25° C. A number of dead insect(s) after 6 days was counted and a rate of dead insects was calculated by the calculation equation similar to that in Test Example 1. Incidentally, the test was carried out with two districts.
  • As a result, the following compounds showed an insecticidal rate of 80% or more among the compounds tested.
    The compounds of the present invention: No. 1-011, 1-182, 2-024*, 2-025*, 2-026*, 2-028*, 2-029*, 2-033, 2-034*, 2-035*, 2-037*, 2-044*, 2-047, 2-050, 2-051, 2-058˜2-062, 2-065, 2-066, 3-068, 3-079, 3-090, 3-112, 3-125, 3-151, 4-003, 4-006, 5-001, 5-003, 5-005, 5-007, 5-009, 5-011, 5-013˜5-015, 5-021˜5-023, 5-029, 5-035, 5-037˜5-041, 5-045˜5-053, 5-057˜5-061, 5-063, 5-065, 5-067˜5-075, 5-075(+), 5-076˜5-078, 5-079*, 5-081, 5-084˜5-089, 5-090*, 5-091˜5-094, 5-099˜5-104, 5-112˜5-114, 5-117, 5-118, 5-120*, 5-122, 5-123, 5-126, 5-128, 5-130, 5-137˜5-142, 5-143*, 5-144, 5-145, 5-146*, 5-148, 5-151, 5-151(+), 5-153*, 5-154, 5-156, 5-158˜5-160, 5-161*, 5-162, 5-164, 5-165, 5-167*, 5-171, 5-180, 5-182˜5-188, 5-189(+), 5-191, 5-193, 5-201, 5-202, 5-205˜5-207, 5-208*, 5-209˜5-216, 5-218, 5-219, 5-219(+), 5-220˜5-223, 5-225˜5-234, 5-236, 5-238˜5-242, 5-245∫5-247, 5-249, 5-254, 5-258*, 5-261, 5-264, 5-273˜5-275, 5-277˜5-279, 5-281, 5-285˜5-288, 5-291, 5-292, 5-294, 5-295, 5-297, 5-299, 5-301, 5-306, 5-309, 5-310*, 5-312˜5-315, 5-318, 5-319, 5-321, 5-323, 5-330, 5-332, 5-335, 5-339, 5-341, 5-344, 5-345, 5-353˜5-358, 5-359*, 5-360, 5-362, 5-374, 5-375, 5-378, 5-379*, 5-380*, 5-381*, 5-383, 5-384, 5-385*, 5-387˜5-393, 5-396*, 5-397˜5-401, 5-405, 5-409, 5-410, 5-412, 5-417, 5-418, 5-421˜5-423, 5-426˜5-428, 5-430, 5-433, 5-434, 5-440, 5-446, 5-453, 5-455, 5-458, 5-460, 5-461, 5-463˜5-465, 5-468˜5-488, 5-490˜5-498, 5-509, 5-510, 5-515, 5-516, 5-519, 5-521˜5-523, 5-525, 5-527˜5-532, 5-538, 5-539, 5-541, 5-543, 5-549, 5-551˜5-555, 5-557, 5-558, 5-560, 5-562, 5-569˜5-576, 5-579, 5-583˜5-589, 5-600, 5-604˜5-607, 5-611, 5-612, 5-616˜5-619, 5-623, 5-628, 5-630, 5-631, 5-637˜5-639, 5-642, 5-646˜5-648, 5-650˜5-657, 5-660˜5-662, 5-664, 5-665, 5-667, 5-668, 5-671, 5-672, 5-674, 5-684˜5-686, 6-001, 6-003, 6-009, 6-011˜6˜013, 6-016˜6-018, 6-020, 6-021, 6-022*, 6-027, 6-028, 6-031˜6-041, 6-043, 6-044, 6-048˜6-050, 6-056, 6-074˜6-076, 6-078, 6-079, 6-081, 6-083, 6-089, 6-090, 6-093, 6-095, 6-096, 6-098, 6-100, 6-102, 6-110, 6-114, 6-124, 6-130˜6-132, 7-001, 7-003˜7-006, 7-008˜7-010, 11-017, 11-024, 11-026, 11-028, 11-056, 11-099, 11-120, 11-125, 11-132.
    In the interim, the indication of “*” shows that the insecticidal test was carried out by use of a chemical solution of a concentration of 100 ppm.
    • Test Example 12 Insecticidal Test Against Green Peach Aphid
  • A wet cotton wool was laid in a laboratory dish having an inner diameter of 3 cm, a leaf of a cabbage cut out so as to have the same diameter was laid thereon, and 4-green peach aphid (Myzus persicae) in the stage of no-wing adult was left. After 1 day, a 10% emulsifiable concentrate (depending on the compounds, 10% wettable powder was applied for the test) of the compound of the present invention was diluted with water containing a spreading agent to prepare a chemical solution with a concentration of 500 ppm, and the chemical solution was sprayed with a rotating spray tower (2.5 mg/cm2), and the laboratory dish was covered with lids and contained at a thermostat chamber at 25° C. A number of dead insect(s) after 6 days was counted and a rate of dead insects was calculated by the calculation equation similar to that in Test Example 1. Incidentally, the test was carried out with two districts.
  • As a result, the following compounds showed an insecticidal rate of 80% or more among the compounds tested.
    The compounds of the present invention:
    No. 1-006, 1-063, 1-067, 1-069, 1-153, 1-158, 1-163, 1-166, 1-167, 1-171, 1-175, 1-207, 1-209, 1-215, 2-005, 2-015, 2-017, 2-024*, 2-025*, 2-026*, 2-027, 2-029*, 2-034*, 2-044*, 2-046*, 2-050, 2-051, 2-057˜2-059, 2-062, 2-065, 2-066, 3-006, 3-029, 3-064, 3-068, 3-089, 3-110, 3-114, 3-125, 3-131, 3-139, 3-143, 4-003, 5-001, 5-003, 5-005, 5-009, 5-013, 5-015, 5-022, 5-023, 5-037˜5-041, 5-045˜5-050, 5-052, 5-053, 5-056, 5-058˜5-061, 5-063, 5-065˜5-068, 5-070˜5-075, 5-075(+), 5-076, 5-077, 5-079*, 5-081, 5-083˜5-086, 5-090*, 5-091˜5-094, 5-099, 5-100, 5-102, 5-103, 5-113, 5-117, 5-118, 5-128, 5-130, 5-134, 5-138˜5-142, 5-143*, 5-144, 5-145, 5-146*, 5-147, 5-148, 5-151, 5-151(+), 5-153*, 5-154, 5-156, 5-158, 5-160, 5-161*, 5-162, 5-165, 5-180˜5-187, 5-189(+), 5-193, 5-202, 5-205, 5-209, 5-210, 5-212, 5-214˜5-216, 5-219, 5-219(+), 5-220˜5-223, 5-226, 5-228, 5-230, 5-231, 5-233, 5-234, 5-236, 5-238, 5-240, 5-242, 5-243*, 5-245˜5-247, 5-251, 5-254, 5-256, 5-258*, 5-259, 5-261, 5-264, 5-272˜5-275, 5-277˜5-280, 5-282, 5-284˜5-288, 5-291, 5-294, 5-295, 5-300, 5-301, 5-306, 5-307, 5-309, 5-310*, 5-313˜5-315, 5-320, 5-321, 5-323, 5-330, 5-334, 5-335, 5-339, 5-341, 5-343, 5-344, 5-348, 5-352, 5-353˜5-358, 5-359*, 5-360, 5-362, 5-364, 5-374, 5-375, 5-378, 5-379*, 5-380*, 5-383, 5-384, 5-385*, 5-387, 5-389, 5-390, 5-392, 5-393, 5-398, 5-399, 5-401, 5-409, 5-410, 5-415, 5-418, 5-421˜5-424, 5-427, 5-428, 5-433, 5-434, 5-440˜5-442, 5-446, 5-453, 5-455, 5-458˜5-465, 5-468, 5-470˜5-484, 5-486, 5-487, 5-490, 5-491, 5-494˜5-499, 5-510, 5-512, 5-515, 5-516, 5-519, 5-523, 5-527˜5-529, 5-532, 5-538, 5-541, 5-541(S), 5-546, 5-551˜5-554, 5-557, 5-558, 5-560, 5-569˜5-576, 5-581, 5-583, 5-587, 5-588, 5-608, 5-611, 5-612, 5-617, 5-619, 5-628, 5-630˜5-632, 5-637, 5-638, 5-642, 5-644, 5-646, 5-654, 5-655, 5-662, 5-664, 5-669, 5-670, 5-672, 5-674, 5-684, 5-686, 6-001, 6-003, 6-005*, 6-007, 6-009˜6-012, 6-015*, 6-016˜6-021, 6-022*, 6-027, 6-028, 6-030˜6-033, 6-035˜6-044, 6-048˜6-050, 6-054, 6-056˜6-059, 6-063, 6-066, 6-074˜6-076, 6-078˜6-084, 6-086, 6-089˜6-095, 6-097, 6-098, 6-100˜6-103, 6-112, 6-114, 6-115, 6-121, 6-124, 6-130˜6-132, 7-003˜7-007, 7-009, 8-005, 8-006, 9-004, 9-009, 10-002, 10-006, 11-005, 11-006, 11-026, 11-118, 11-125, 11-130, 12-004.
    In the interim, the indication of “*” shows that the insecticidal test was carried out by use of a chemical solution of a concentration of 100 ppm.
    • Test Example 13 Insecticidal Test Against Japanese Mealybug
  • A wet filter paper was laid in a styrol cup having an inner diameter of 7 cm, a leaf of a common bean cut out so as to have the same diameter was laid thereon, and 10-Japanese mealybug (Planococcus kraunhiae) in the first instar larva per leaf was inoculated thereon. A 10% emulsifiable concentrate (depending on the compounds, 10% wettable powder was applied for the test) of the compound of the present invention was diluted with water containing a spreading agent to prepare a chemical solution with a concentration of 500 ppm. The chemical solution was sprayed with a rotating spray tower in an amount of 2.5 ml per styrol cup, and the styrol cups were covered with lids and contained at a thermostat chamber at 25° C. A number of dead insect(s) after 6 days was counted and a rate of dead insects was calculated by the calculation equation similar to that in Test Example 1. Incidentally, the test was carried out with two districts.
  • As a result, the following compounds showed an insecticidal rate of 80% or more among the compounds tested.
  • The compounds of the present invention: No. 1-011, 1-177, 1-182, 2-020, 2-028*, 2-029*, 2-033, 2-034*, 2-035*, 2-037*, 2-039*, 2-040*, 2-041*, 2-042*, 2-044*, 2-045*, 2-046*, 2-047, 2-048*, 2-049*, 2-050˜2-052, 2-055*, 2-057, 2-059, 2-062, 2-065˜2-067, 3-065, 3-069, 3-085, 3-086, 3-091˜3-093, 3-104, 3-109, 3-125, 3-151, 4-003, 4-004, 4-006, 5-001, 5-003, 5-005, 5-007, 5-009, 5-013˜5-015, 5-017, 5-022, 5-023, 5-029, 5-037, 5-039˜5-041, 5-045˜5-050, 5-052, 5-053, 5-057˜5-061, 5-063˜5-065, 5-067˜5-075, 5-075(+), 5-076˜5-078, 5-081, 5-083˜5-089, 5-090*, 5-091˜5-094, 5-098˜5-105, 5-109, 5-111˜5-114, 5-116˜5-118, 5-121, 5-123, 5-126, 5-128, 5-129*, 5-130, 5-131*, 5-138˜5-142, 5-143*, 5-144, 5-145, 5-146*, 5-147, 5-148, 5-151, 5-151(+), 5-153*, 5-154, 5-156, 5-158˜5-160, 5-161*, 5-162, 5-164, 5-165, 5-166, 5-167*, 5-168*, 5-171, 5-172*, 5-179˜5-188, 5-189(+), 5-190(+), 5-192˜5-194, 5-201, 5-202, 5-205, 5-206, 5-208*, 5-210˜5-212, 5-214˜5-216, 5-219, 5-219(+), 5-221, 5-222, 5-223, 5-226˜5-234, 5-236˜5-240, 5-242, 5-245˜5-247, 5-249, 5-251, 5-253, 5-254, 5-255*, 5-256, 5-257, 5-258*, 5-259, 5-261, 5-264, 5-269*, 5-271*, 5-272˜5-288, 5-291, 5-292, 5-295˜5-297, 5-299˜5-301, 5-302*, 5-303, 5-306, 5-307, 5-309, 5-310*, 5-312˜5-315, 5-318, 5-319, 5-321, 5-322, 5-323, 5-331, 5-332, 5-334˜5-336, 5-338, 5-339, 5-344, 5-345, 5-348, 5-349, 5-353˜-358, 5-360˜5-362, 5-375, 5-378, 5-379*, 5-380*, 5-381*, 5-383, 5-384, 5-385*, 5-387, 5-388, 5-390, 5-392, 5-393, 5-395, 5-396*, 5-397˜5-399, 5-401, 5-406, 5-407, 5-410, 5-412, 5-417˜5-419, 5-422˜5-424, 5-426˜5-434, 5-439˜5-443, 5-445, 5-446, 5-452, 5-453, 5-457, 5-458, 5-460, 5-461, 5-463˜5-465, 5-468, 5-470˜5-473, 5-475˜5-477, 5-480, 5-482˜5-485, 5-487, 5-488, 5-490˜5-492, 5-494˜5-496, 5-498, 5-500, 5-516, 5-519, 5-521˜5-523, 5-525, 5-527, 5-531, 5-532, 5-538, 5-541, 5-543, 5-546, 5-547, 5-549˜5-554, 5-558, 5-569, 5-572˜5-576, 5-579, 5-581˜5-584, 5-587, 5-589, 5-599, 5-605, 5-607, 5-616, 5-623, 5-627, 5-628, 5-637, 5-638, 5-647, 5-651, 5-654˜5-656, 5-658˜5-662, 5-664˜5-666, 5-668˜5-672, 5-674, 5-684˜5-686, 6-001˜6-003, 6-005*, 6-006*, 6-007˜6-013, 6-015*, 6-016˜6-021, 6-022*˜6-023, 6-024*, 6-025*, 6-026˜6-050, 6-054˜6-056, 6-058, 6-059, 6-063, 6-066, 6-074˜6-076, 6-078˜6-080, 6-080(+), 6-082˜6-085, 6-089, 6-090˜6-096, 6-098˜6-102, 6-103, 6-110, 6-114, 6-115, 6-130˜6-132, 7-003˜7-010, 8-003, 9-003, 9-011, 10-002, 10-006, 11-024˜11-026, 11-043, 11-045, 11-056, 11-058, 11-059, 11-089, 11-120, 11-125, 11-132, 12-006, 12-008.
  • In the interim, the indication of “*” shows that the insecticidal test was carried out by use of a chemical solution of a concentration of 100 ppm.
    • Test Example 14 Insecticidal Test Against Cucurbit Leaf Beetle
  • A 10% emulsifiable concentrate (depending on the compounds, 10% wettable powder was applied for the test) of the compound of the present invention was diluted with water containing a spreading agent to prepare a chemical solution with a concentration of 500 ppm. To the chemical solution was dipped leaves of cucumber for about 10 seconds, and after air-drying, they were placed in a laboratory dish, then 5-cucurbit leaf beetle (Aulacophora femoralis) in the stage of second instar larva per the dish were released therein, and the dish was covered with a lid and contained at a thermostat chamber at 25° C. A number of dead insect(s) after 6 days was counted and a rate of dead insects was calculated by the calculation equation similar to that in Test Example 1. Incidentally, the test was carried out with two districts.
  • As a result, the following compounds showed an insecticidal rate of 80% or more among the compounds tested.
  • The compounds of the present invention: No. 1-005, 1-015, 1-016, 1-040, 1-042, 1-055˜1-057, 1-059, 1-061˜1-067, 1-069˜1-071, 1-073, 1-074, 1-076, 1-077, 1-079˜1-081, 1-083˜1-085, 1-087, 1-088, 1-090, 1-092˜1-095, 1-098, 1-099, 1-102, 1-104˜1-110, 1-113, 1-116, 1-118, 1-119, 1-122˜1-129, 1-131, 1-135, 1-136, 1-138, 1-146, 1-147, 1-151˜1-153, 1-155˜1-157, 1-159, 1-166, 1-167, 1-171, 1-172, 1-174˜1-177, 1-179˜1-185, 1-187˜1-189, 1-194, 1-199, 1-206, 1-207, 1-210, 1-212, 1-214, 1-215, 1-220, 1-225, 2-001, 2-004, 2-006, 2-011, 2-013, 2-019˜2-022, 2-025˜2-029, 2-031, 2-032, 2-034˜2-055, 2-057˜2-068, 3-002, 3-003, 3-006, 3-011, 3-018, 3-025˜3-028, 3-031˜3-035, 3-037, 3-044, 3-046, 3-047, 3-050, 3-058, 3-061˜3-065, 3-068˜3-072, 3-074, 3-076, 3-078˜3-081, 3-084˜3-087, 3-089˜3-095, 3-097˜3-116, 3-118˜3-125, 3-127˜3-132, 3-134˜3-136, 3-138˜3-143, 3-145˜3-151, 4-003˜4-007, 4-009˜4-011, 5-001˜5-015, 5-017, 5-021˜5-023, 5-028˜5-042, 5-044˜5-075, 5-075(+), 5-075(−), 5-076˜5-081, 5-083˜5-095, 5-097, 5-099˜5-107, 5-109˜5-130, 5-132˜5-135, 5-137˜5-151, 5-151(+), 5-151(−), 5-152˜5-156, 5-158˜5-189, 5-189(+), 5-190(+), 5-191˜5-219, 5-219(+), 5-219(−), 5-220˜5-236, 5-238˜5-296, 5-298˜5-326, 5-329˜5-339, 5-34˜5-350, 5-352˜5-363, 5-365, 5-369, 5-371, 5-374˜5-403, 5-405˜5-413, 5-415˜5-447, 5-449, 5-452˜5-455, 5-458˜5-491, 5-493˜5-503, 5-505, 5-507˜5-534, 5-536˜5-540, 5-540(+), 5-541, 5-541(R), 5-541(S), 5-542˜5-560, 5-562˜5-570, 5-572˜5-590, 5-592˜5-602, 5-604˜5-609, 5-611˜5-619, 5-621˜5-648, 5-650, 5-651, 5-653˜5-672, 5-674, 5-676, 5-678, 5-684˜5-686, 6-001˜6-013, 6-015˜6-024, 6-026˜6-051, 6-053˜6-067, 6-070, 6-071, 6-074˜6-080, 6-080(46-080(−), 6-081˜6-086, 6-089˜6-096, 6-098˜6-106, 6-108˜6-115, 6-117˜6-127, 6-129˜6-133, 7-001˜7-010, 8-001˜8-007, 9-003, 9-009, 9-010, 10-002˜10-005, 11-005, 11-015, 11-017, 11-020, 11-023˜11-026, 11-038, 11-043, 11-045, 11-046, 11-052˜11-054, 11-056˜11-060, 11-066, 11-067, 11-072, 11-076, 11-098, 11-099, 11-101˜11-104, 11-106, 11-108, 11-110, 11-112˜11-114, 11-119, 11-120, 11-124, 11-125, 11-129, 11-130, 11-132, 12-006.
    • Test Example 15 Insecticidal Test Against Serpentine Leaf Miner
  • A 10% emulsifiable concentrate (depending on the compounds, 10% wettable powder was applied for the test) of the compound of the present invention was diluted with water containing a spreading agent to prepare a chemical solution with a concentration of 500 ppm. To the chemical solution was dipped leaves of common bean on which serpentine leaf miner (Liriomyza trifolii) laid eggs (10 eggs/leaf) for about 10 seconds, and after air-drying, they were placed on a wet filter paper laid in a styrol cup having an inner diameter of 7 cm, and the styrol cup was covered with a lid and contained at a thermostat chamber at 25° C. A number of dead insect(s) after 6 days was counted and a rate of dead insects was calculated by the calculation equation similar to that in Test Example 1. Incidentally, the test was carried out with two districts.
  • As a result, the following compounds showed an insecticidal rate of 80% or more among the compounds tested.
  • The compounds of the present invention: No. 1-175, 1-177, 2-029*, 2-034*, 2-035*, 2-044*, 2-045*, 2-050, 2-051, 2-057, 2-059, 2-062, 2-064, 2-065, 2-067, 3-060, 3-068, 3-069, 3-071, 3-072*, 3-085, 3-086, 3-093, 3-105, 3-109, 3-112, 3-125, 3-148, 3-151, 5-001, 5-003, 5-005, 5-007, 5-009, 5-015, 5-022, 5-023, 5-036, 5-037, 5-040, 5-041, 5-045˜5-053, 5-058˜5-061, 5-063˜5-065, 5-067, 5-068, 5-070˜5-075, 5-075(+), 5-076, 5-077, 5-081, 5-083, 5-085˜5-089, 5-090*, 5-091˜5-094, 5-099˜5-105, 5-113, 5-117˜5-119, 5-120*, 5-121˜5-123, 5-124*, 5-126, 5-129*, 5-131*, 5-133*, 5-138˜5-142, 5-144, 5-145, 5-147, 5-148, 5-150, 5-151, 5-151(+), 5-154, 5-156, 5-158, 5-160, 5-161*, 5-162, 5-164˜5-166, 5-168*, 5-169, 5-171, 5-172*, 5-178, 5-180, 5-182˜5-188, 5-189(+), 5-201, 5-202, 5-208*, 5-209, 5-210, 5-212, 5-214˜5-216, 5-217*, 5-219, 5-219(+), 5-221˜5-223, 5-226˜5-234, 5-236, 5-238, 5-239, 5-241, 5-245˜5-247, 5-251, 5-256, 5-257, 5-258*, 5-259, 5-261, 5-264, 5-265, 5-270, 5-274, 5-275, 5-283, 5-284, 5-286, 5-291, 5-294, 5-295, 5-302*, 5-303, 5-306, 5-309, 5-310*, 5-313˜5-315, 5-319, 5-323, 5-335, 5-336, 5-338, 5-339, 5-341, 5-344, 5-345, 5-353˜5-358, 5-360, 5-362, 5-374, 5-375, 5-378, 5-379*, 5-380*, 5-381*, 5-383, 5-384, 5-385*, 5-387, 5-388, 5-390, 5-392, 5-393, 5-395, 5-396*, 5-397˜5-401, 5-408˜5-413, 5-415, 5-417˜5-423, 5-425˜5-430, 5-432, 5-433, 5-439˜5-441, 5-443, 5-445, 5-446, 5-452, 5-453, 5-455, 5-458˜5-465, 5-467, 5-468, 5-470˜5-488, 5-490, 5-491, 5-494˜5-499, 5-501, 5-508˜5-512, 5-515˜5-517, 5-519, 5-520˜5-523, 5-527˜5-532, 5-538, 5-539, 5-541, 5-541(S), 5-543, 5-549, 5-551˜5-554, 5-556˜5-560, 5-566, 5-569, 5-570, 5-572˜5-576, 5-579, 5-581, 5-584, 5-596, 5-601, 5-606, 5-616, 5-617, 5-630, 5-631, 5-634, 5-635, 5-637, 5-638, 5-642, 5-643, 5-646, 5-651, 5-653˜5-657, 5-659, 5-660, 5-662, 5-664˜5-672, 5-674, 5-684˜5-686, 6-001, 6-004*, 6-005*, 6-006*, 6-007, 6-008, 6-011˜6-013, 6-015*, 6-016˜6-021, 6-022*, 6-024*, 6-025*, 6-027, 6-031, 6-033˜6-041, 6-043, 6-044, 6-048˜6-050, 6-054˜6-056, 6-066, 6-070, 6-074˜6-076, 6-078, 6-079, 6-081, 6-083, 6-085, 6-089, 6-091, 6-092, 6-093, 6-095, 6-098, 6-100, 6-102, 6-103, 6-110, 6-114, 6-123, 6-124, 6-129˜6-133, 7-003, 7-005˜7-009.
  • In the interim, the indication of “*” shows that the insecticidal test was carried out by use of a chemical solution of a concentration of 100 ppm.
    • Test Example 16 Insecticidal Test Against Two-Spotted Spider Mite
  • A wet filter paper was laid in a styrol cup having an inner diameter of 7 cm, a leaf of a common bean cut out so as to have the same diameter was laid thereon, and 10 larvae of two-spotted spider mite (Tetranychus urticae) per leaf was inoculated thereon. A 10% emulsifiable concentrate (depending on the compounds, 10% wettable powder was applied for the test) of the compound of the present invention was diluted with water containing a spreading agent to prepare a chemical solution with a concentration of 500 ppm. The chemical solution was sprayed with a rotating spray tower in an amount of 2.5 ml per styrol cup, and the styrol cups were covered with lids and contained at a thermostat chamber at 25° C. A number of dead insect(s) after 6 days was counted and a rate of dead insects was calculated by the calculation equation similar to that in Test Example 1. Incidentally, the test was carried out with two districts.
  • As a result, the following compounds showed an insecticidal rate of 80% or more among the compounds tested.
  • The compounds of the present invention: No. 1-177, 1-182, 2-027, 2-028*, 2-029*, 2-034*, 2-035*, 2-036, 2-037*, 2-039*, 2-040*, 2-041*, 2-042*, 2-044*, 2-045*, 2-046*, 2-047, 2-048*, 2-049*, 2-050˜2-052, 2-057˜2-063, 2-065˜2-067, 3-068, 3-084, 3-086, 3-109, 3-110, 3-112, 3-114, 3-124, 3-131, 3-151, 5-001, 5-003, 5-005, 5-007˜5-009, 5-011, 5-013, 5-015, 5-019, 5-021, 5-022, 5-023, 5-028, 5-029, 5-035˜5-037, 5-040, 5-041, 5-045˜5-053, 5-057˜5-075, 5-075(+), 5-076˜5-078, 5-080˜5-089, 5-090*, 5-091˜5-094, 5-098˜5-105, 5-109, 5-112˜5-114, 5-117˜5-119, 5-121˜5-123, 5-126, 5-128, 5-129*, 5-130, 5-132, 5-134, 5-136˜5-142, 5-143*, 5-144, 5-145, 5-146*, 5-147, 5-148, 5-150, 5-151, 5-151(+), 5-152, 5-153*, 5-154˜5-156, 5-158˜5-160, 5-161*, 5-162˜5-166, 5-167*, 5-168*, 5-171, 5-172*, 5-177˜5-180, 5-182˜5-188, 5-189*, 5-189(+), 5-190(+), 5-191, 5-192, 5-196*, 5-197*, 5-199˜5-202, 5-204˜5-207, 5-208*, 5-209˜5-212, 5-214˜5-216, 5-218, 5-219, 5-219(+), 5-219(−), 5-220˜5-234, 5-235*, 5-236, 5-238˜5-242, 5-243*, 5-245˜5-247, 5-249, 5-251, 5-254, 5-255*, 5-256, 5-257, 5-258*, 5-259, 5-261, 5-264, 5-265, 5-269*, 5-271*, 5-273˜5-275, 5-277˜5-279, 5-283˜5-286, 5-288, 5-291, 5-292, 5-294, 5-295, 5-299˜5-301, 5-306, 5-307, 5-312˜5˜316, 5-321, 5-323, 5-325, 5-330, 5-336, 5-338, 5-339, 5-341, 5-344, 5-345, 5-349, 5-353˜5-358, 5-360, 5-362, 5-374, 5-375, 5-376*, 5-377*, 5-378, 5-379*, 5-380*, 5-381*, 5-383, 5-384, 5-385*, 5-386*, 5-387˜5-395, 5-396*, 5-397˜5-399, 5-401, 5-402, 5-405, 5-406, 5-408˜5-413, 5-415, 5-417˜5-419, 5-421˜5-423, 5-425˜5-427, 5-430, 5-432, 5-433, 5-440, 5-441, 5-443, 5-445, 5-452˜5-455, 5-457˜5-463, 5-465, 5-467, 5-468, 5-470˜5-487, 5-489˜5-492, 5-494˜5-499, 5-503, 5-505, 5-506, 5-509˜5-513, 5-515˜5-525, 5-527˜5-534, 5-538, 5-539, 5-540(+), 5-543˜5-545, 5-548˜5-554, 5-557˜5-560, 5-566, 5-568˜5-570, 5-572˜5-576, 5-578, 5-579, 5-581, 5-583, 5-584, 5-600, 5-601, 5-604, 5-606, 5-616, 5-617, 5-630, 5-631, 5-635, 5-637, 5-638, 5-642, 5-646, 5-647, 5-650, 5-651, 5-654˜5-657, 5-659˜5-662, 5-664˜5-672, 5-678, 5-684˜5-686, 6-001, 6-003, 6-007, 6-008, 6-011˜6-013, 6-015*, 6-016˜6-021, 6-023, 6-027, 6-030˜6-044, 6-046˜6-050, 6-054˜6-056, 6-066, 6-074˜6-076, 6-078, 6-079, 6-082˜6-085, 6-089˜6-093, 6-095, 6-096, 6-098, 6-100, 6-102, 6-103, 6-110, 6-112, 6-114, 6-115, 6-121, 6-123, 6-124, 6-129˜6-133, 7-003˜7-010, 8-003, 10-002, 10-006, 11-026, 11-098, 11-108, 12-002.
  • In the interim, the indication of “*” shows that the insecticidal test was carried out by use of a chemical solution of a concentration of 100 ppm.
    • Test Example 17 Insecticidal Test Against Pink Citrus Rust Mite
  • A wet filter paper was laid in a styrol cup having an inner diameter of 7 cm, a leaf of a mandarin orange cut out so as to have the same diameter was laid thereon, and 10 larvae of pink citrus rust mite (Aculops pelekassi) per leaf was inoculated thereon. A 10% emulsifiable concentrate (depending on the compounds, 10% wettable powder was applied for the test) of the compound of the present invention was diluted with water containing a spreading agent to prepare a chemical solution with a concentration of 100 ppm. The chemical solution was sprayed with a rotating spray tower in an amount of 2.5 ml per styrol cup, and the styrol cups were covered with lids and contained at a thermostat chamber at 25° C. A number of dead insect(s) after 6 days was counted and a rate of dead insects was calculated by the calculation equation similar to that in Test Example 1. Incidentally, the test was carried out with two districts.
  • As a result, the following compounds showed an insecticidal rate of 80% or more among the compounds tested.
    The compounds of the present invention: No. 1-177, 3-093, 3-112, 5-001˜5-003, 5-005, 5-008, 5-009, 5-022, 5-023, 5-036, 5-037, 5-040, 5-041, 5-046, 5-047, 5-049, 5-050, 5-053, 5-057˜5-059, 5-061, 5-063, 5-065, 5-066, 5-069˜5-071, 5-074˜5-077, 5-081, 5-083, 5-084, 5-086, 5-088, 5-111˜5-113, 5-121, 5-137˜5-140, 5-148, 5-151, 5-174, 5-182, 5-183, 5-185, 5-187, 5-188, 5-202, 5-205, 5-206, 5-215, 5-216, 5-219˜5-221, 5-225, 5-226, 5-233˜5-235, 5-241, 5-247, 5-274, 5-285, 5-291, 5-294, 5-295, 5-301, 5-313, 5-323, 5-331, 5-334, 5-338, 5-339, 5-355, 5-360, 5-374, 5-378, 5-387˜5-390, 5-393, 5-397, 5-398, 5-480, 5-494, 5-638, 5-642, 5-645, 6-003, 6-017, 6-020, 6-021, 6-027, 6-031, 6-033˜6-035, 6-043, 6-049, 6-054, 6-064, 6-070, 6-076, 6-131, 7-003, 7-007˜7-009, 10-002.
    • Test Example 18 Insecticidal Test Against Broad Mite
  • A wet filter paper was laid in a styrol cup having an inner diameter of 7 cm, a leaf of a common bean cut out so as to have the same diameter was laid thereon, and 10 adults of broad mite (Polyphagotarsonemus latus) per leaf was inoculated thereon. A 10% emulsifiable concentrate (depending on the compounds, 10% wettable powder was applied for the test) of the compound of the present invention was diluted with water containing a spreading agent to prepare a chemical solution with a concentration of 100 ppm. The chemical solution was sprayed with a rotating spray tower in an amount of 2.5 ml per styrol cup, and the styrol cups were covered with lids and contained at a thermostat chamber at 25° C. A number of dead insect(s) after 2 days was counted and a rate of dead insects was calculated by the calculation equation similar to that in Test Example 1. Incidentally, the test was carried out with two districts.
  • As a result, the following compounds showed an insecticidal rate of 80% or more among the compounds tested.
  • The compounds of the present invention:
    No. 3-093, 5-009, 5-036, 5-037, 5-040, 5-041, 5-050, 5-053, 5-058, 5-063, 5-067, 5-071, 5-075˜5-077, 5-083, 5-088, 5-089, 5-113, 5-121, 5-140, 5-147, 5-148, 5-151, 5-174, 5-179, 5-185, 5-188, 5-214, 5-215, 5-219, 5-230, 5-233˜5-236, 5-249, 5-251, 5-254, 5-274, 5-288, 5-289, 5-291, 5-294, 5-309, 5-332, 5-339, 5-355, 5-360, 5-374, 5-375, 5-387, 5-398, 5-474, 5-476, 5-480, 5-494, 5-604, 5-642, 6-017, 6-026, 6-031, 6-033˜6-035, 6-038, 6-045, 6-064, 6-070, 6-076, 6-131, 7-003, 7-007˜7-009.
    • Test Example 19 Insecticidal Test Against Ctenocephalides felis
  • After 400 l of acetone solution in which 4 mg of the compound of the present invention was dissolved in 40 ml of acetone (concentration 100 ppm) was coated on the bottom face and side face of a laboratory dish having an inner diameter of 5.3 cm, acetone was vaporized to prepare a thin film of the compound of the present invention on the inner wall of the laboratory dish. As the surface area of the inner wall is 40 cm2, the treated dosage is 1 g/cm2. 10 adults of Ctenocephalides felis (male and female are mixed) were left in the laboratory dish, covered with lid and contained at a thermostat chamber at 25° C. A number of dead insect(s) after 4 days was counted and a rate of dead insects was calculated by the calculation equation similar to that in Test Example 1. Incidentally, the test was carried out with one district.
  • As a result, the following compounds showed an insecticidal rate of 80% or more among the compounds tested.
    The compounds of the present invention: No. 2-029*, 2-052, 3-151, 5-002, 5-003, 5-005, 5-007, 5-008, 5-012, 5-013, 5-023, 5-029, 5-037, 5-058, 5-071*, 5-072, 5-075*, 5-076*, 5-077, 5-086, 5-088*, 5-093*, 5-100*, 5-101*, 5-111*, 5-117, 5-121, 5-130*, 5-138, 5-139, 5-140*, 5-142*, 5-148*, 5-151*, 5-160*, 5-161*, 5-165*, 5-174*, 5-182*, 5-184, 5-187, 5-188, 5-192, 5-205, 5-206, 5-209, 5-214*, 5-215*, 5-218, 5-219*, 5-223, 5-229, 5-230, 5-232, 5-234*, 5-235*, 5-236, 5-238, 5-240, 5-241*, 5-243*, 5-245*, 5-247, 5-264, 5-274*, 5-287, 5-291, 5-294, 5-310*, 5-312, 5-313, 5-323, 5-354*, 5-356*, 5-359*, 5-360, 5-362, 5-376*, 5-377*, 5-378*, 5-379*, 5-383*, 5-384*, 5-387*, 5-389*, 5-390, 5-393, 5-399*, 5-401*, 5-405*, 5-412*, 5-423*, 5-427*, 5-429*, 5-430*, 5-440*, 5-461*, 5-466*, 5-468*, 5-470*, 5-473, 5-474*, 5-475, 5-476, 5-477*, 5-478*, 5-480*, 5-487, 5-494*, 5-495˜5-499, 5-579*, 5-587*, 5-623, 5-646*, 5-648*, 5-658, 6-020, 6-026, 6-033, 6-034*, 6-035*, 6-043*, 6-046˜6-049, 6-054, 6-055, 6-064*, 6-065*, 6-074, 6-092, 6-094, 6-095, 6-129, 6-130, 6-133, 7-002*, 7-004, 7-008*, 7-009.
    In the interim, the indication of “*” shows that the insecticidal test was carried out with a treated dosage of 0.1 g/cm2.
    • Test Example 20 Insecticidal Test Against American Dog Tick
  • After 400 l of acetone solution in which 4 mg of the compound of the present invention was dissolved in 40 ml of acetone (concentration 100 ppm) was coated on the bottom face and side face of two laboratory dishes having an inner diameter of 5.3 cm, acetone was vaporized to prepare a thin film of the compound of the present invention on the inner wall of the laboratory dish. As the surface area of the inner wall is 40 cm2, the treated dosage is 1 g/cm2. 10-American dog tick (Dermacentor variabilis) (male and female are mixed) in the stage of protonymph were left in the laboratory dishes, two laboratory dishes together were sealed with a tape so that ticks do not escape, and contained at a thermostat chamber at 25° C. A number of dead insect(s) after 4 days was counted and a rate of dead insects was calculated by the calculation equation similar to that in Test Example 1. Incidentally, the test was carried out with one district.
  • As a result, the following compounds showed an insecticidal rate of 80% or more among the compounds tested.
  • The compounds of the present invention: No. 2-029*, 2-052, 2-054*, 5-003, 5-005, 5-008, 5-023, 5-029, 5-037, 5-058, 5-063*, 5-071*, 5-072, 5-075*, 5-076*, 5-077, 5-086, 5-088*, 5-093*, 5-100*, 5-101*, 5-117, 5-121, 5-128, 5-130*, 5-138, 5-139, 5-140*, 5-142*, 5-148*, 5-151*, 5-160*, 5-161*, 5-165*, 5-174*, 5-182*, 5-184, 5-187, 5-188, 5-191, 5-192, 5-205, 5-206, 5-209, 5-214*, 5-215*, 5-219*, 5-223, 5-229, 5-230, 5-232, 5-233*, 5-234*, 5-235*, 5-236, 5-238, 5-240, 5-241*, 5-243*, 5-245*, 5-247, 5-264, 5-274*, 5-287, 5-291, 5-294, 5-308*, 5-309*, 5-310*, 5-312, 5-313, 5-320, 5-321, 5-323, 5-354*, 5-356*, 5-359*, 5-360, 5-362, 5-376*, 5-377*, 5-378*, 5-379*, 5-383*, 5-384*, 5-386*, 5-387*, 5-390, 5-393, 5-399*, 5-401*, 5-405*, 5-412*, 5-418*, 5-423*, 5-427*, 5-429*, 5-430*, 5-432*, 5-440*, 5-461*, 5-466*, 5-468*, 5-469*, 5-470*, 5-473*, 5-474*, 5-475*, 5-476*, 5-477*, 5-478*, 5-480*, 5-487*, 5-494*, 5-495*, 5-496*, 5-497*, 5-498*, 5-499*, 5-500*, 5-555*, 5-579*, 5-581*, 5-585*, 5-587*, 5-588*, 5-589*, 5-593*, 5-601*, 5-607*, 5-610*, 5-623*, 5-638*, 5-646*, 5-648*, 5-654*, 5-658*, 6-020, 6-026, 6-033, 6-034*, 6-035*, 6-043*, 6-046˜6-049, 6-054, 6-055, 6-064*, 6-065*, 6-074, 6-092*, 6-094*, 6-095*, 6-129*, 6-130*, 6-133*, 7-004, 7-008*, 7-009, 11-056.
  • In the interim, the indication of “*” shows that the insecticidal test was carried out with a treated dosage of 0.1 g/cm2.
    • Test Example 21 Insecticidal Test Against German Cockroach
  • A chemical solution having a concentration of 10 g/l was prepared by diluting the compound of the present invention with acetone. The chemical solution was coated on the abdominal region of male adults of German cockroach (Blattella germanica) in an amount of 1 l per cockroach, and the treated cockroaches were contained at a thermostat chamber at 25° C. A number of dead insect(s) after 2 days was counted and a rate of dead insects was calculated by the calculation equation similar to that in Test Example 1. Incidentally, the test was carried out with five districts.
  • As a result, the following compounds showed an insecticidal rate of 80% or more among the compounds tested.
    The compounds of the present invention: No. 5-075, 5-140*, 5-147*, 5-148*, 5-151*, 5-174*, 5-234*, 5-412*, 5-480*, 5-494*, 5-541*, 5-638*, 6-103*.
    • Test Example 22 Insecticidal Test Against Musca domestica
  • A chemical solution having a concentration of 1 g/l was prepared by diluting the compound of the present invention with acetone. The chemical solution was coated on the abdominal region of female adults of Musca domestica in an amount of 1 l per fly, and the treated flies were contained at a thermostat chamber at 25° C. A number of dead insect(s) after 2 days was counted and a rate of dead insects was calculated by the calculation equation similar to that in Test Example 1. Incidentally, the test was carried out with ten districts.
  • As a result, the following compounds showed an insecticidal rate of 80% or more among the compounds tested.
    The compounds of the present invention:
    • No. 5-075, 5-140, 5-147, 5-148, 5-151, 5-174, 5-219, 5-234, 5-412, 5-480, 5-494, 5-541, 5-638, 6-103. Test Example 23 Insecticidal Test Against Eastern Subterranean Termite
  • A 10% emulsifiable concentrate (depending on the compounds, 10% wettable powder was applied for the test) of the compound of the present invention was diluted with water containing a spreading agent to prepare a chemical solution with a concentration of 10 ppm. 0.5 ml of the chemical solution was added dropwise in 10 g of sand and mixed. A filter paper and the sand treated with the chemical solution were placed in a laboratory dish in which 1% agar was laid. 10-Eastern subterranean termite (Reticulitermes flavipes) per dish was left and contained at a thermostat chamber at 25° C. A number of dead insect(s) after 2 days was counted and a rate of dead insects was calculated by the calculation equation similar to that in Test Example 1.
  • As a result, the following compounds showed an insecticidal rate of 80% or more among the compounds tested.
    The compounds of the present invention: No. 5-234.
    • Test Example 24 Insecticidal Test Against Rust-Red Flour Beetle
  • A chemical solution having a concentration of 0.1 mg/ml was prepared by diluting the compound of the present invention with acetone. After 10 ml of the chemical solution was added dropwise in 10 g of bran, 20 adults of rust-red flour beetle (Tribolium castaneum) were left therein, and contained at a thermostat chamber at 25° C. A number of dead insect(s) after 2 months was counted and a rate of dead insects was calculated by the calculation equation similar to that in Test Example 1. Incidentally, the test was carried out with two districts.
  • As a result, the following compounds showed an insecticidal rate of 80% or more among the compounds tested.
    The compounds of the present invention: No. 5-234.
    • INDUSTRIAL APPLICABILITY
  • The isoxazoline-substituted benzanilide compounds according to the present invention are extremely useful compounds showing an excellent pesticidal activity, particularly an insecticidal and acaricidal activity, and causing little adverse effect against non-targeted beings such as mammals, fishes and useful insects.
  • LENGTHY TABLES
    The patent application contains a lengthy table section. A copy of the table is available in electronic form from the USPTO web site (http://seqdata.uspto.gov/?pageRequest=docDetail&DocID=US20150105398A1). An electronic copy of the table will also be available from the USPTO upon request and payment of the fee set forth in 37 CFR 1.19(b)(3).

Claims (12)

1-2. (canceled)
3. A method for protecting an animal against fleas comprising oral administration to the animal of an effective amount of one or more isoxazoline-substituted benzamide compounds, an optically active form or the salt thereof according to a formula 1
a pesticidally effective amount of one or more isoxazoline-substituted benzamide compounds, an optically active form or the salt thereof according to a formula 1
Figure US20150105398A1-20150416-C00092
wherein A1, A1 and A3 are carbon atom,
G is benzene ring,
W is oxygen atom,
X is halogen atom, cyano, C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R4 or —OR5,
Y is halogen atom, C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R4 or —OR5,
R1 and R2 independently of each other are hydrogen atom, C1-C12alkyl, C1-C12alkyl arbitrarily substituted with R16, C3-C12cycloalkyl, C3-C12cycloalkyl arbitrarily substituted with R16, —C(O)R9, —C(O)OR9, E-3 to E-7, E-23 to E-27 or E-28,
R3 is C1-C6alkyl arbitrarily substituted with R4,
D-21 to D-23 and D-47 to D-49 are aromatic heterocyclic rings of the following formulae, respectively
Figure US20150105398A1-20150416-C00093
Z is halogen atom, cyano, C1-C6alkyl, C1-C6haloalkyl or C1-C6haloalkoxy, E-2 to E-7, E-23 to E-28 are saturated heterocyclic rings of the following formulae, respectively
Figure US20150105398A1-20150416-C00094
Figure US20150105398A1-20150416-C00095
R4 is halogen atom,
R5 is C1-C6alkyl arbitrarily substituted with R24,
R9 is C1-C6alkyl or C1-C6alkyl arbitrarily with R24,
R16 is halogen atom, —OR25, —S(O)rR27, —C(O)N(R29)R28, D-21 to D-23, D-47 to D-49, E-2 to E-7, E-23 to E-27 or E-28,
R22 is halogen atom, cyano, C1-C6alkyl, C1-C6alkoxy or C1-C6alkylthio,
R24 is halogen atom,
R25 is hydrogen atom, C1-C8alkyl, C1-C8alkyl arbitrarily substituted with R32, —CHO, —C(O)R33, —C(O)OR33, D-21 to D-23, D-47, D-48 or D-49,
R27 is C1-C8alkyl, C1-C8alkyl arbitrarily substituted with R32, D-21 or D-47,
R28 is C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R32, C3-C8cycloalkyl, C3-C8cycloalkyl arbitrarily substituted with R32, C2-C8alkenyl, C2-C8alkenyl arbitrarily substituted with R32 or C2-C8alkynyl,
R29 is hydrogen atom, C1-C6alkyl or C1-C6alkyl arbitrarily substituted with R32,
R32 is halogen atom, cyano, C3-C8cycloalkyl, C3-C8halocycloalkyl, —OH, —OR33, —S(O)rR33, D-21 to D-23, D-47 D-48 or D-49,
R33 is C1-C6alkyl or C1-C6haloalkyl,
m is an integer of 1 to 3
n is an integer of 1,
p2 is an integer of 0 to 2,
p4 is an integer of 0 to 2,
q2 is an integer of 0 to 3,
q3 is an integer of 0 to 3,
q4 is an integer of 0 to 3,
r is an integer of 0 to 2, and
t is an integer of 0.
4. The method of claim 3 wherein
Y is Cl or CH3;
R1 is H;
R2 is C1-C6 alkyl substituted with one R16; and
R16 is OR25, S(O)nR27 or C(O)NR29R28.
5. The method of claim 4 wherein
X is hydrogen, halogen, C1-C6 alkyl arbitrarily substituted with R4, or OR5;
and each X may be identical with or different from each other.
6. The method of claim 5 wherein
Y is CH3; and
R16 is C(O)NR29R28.
7. The method of claim 6 wherein
Xm is 3-CF3-5-CF3.
8. The method of claim 6 wherein
R29 is H; and R28 is C1-C6 alkyl or C1-C6 alkyl substituted with halogen.
9. The method of claim 6 wherein
R29 is H; and R28 is cyclopropyl.
10. The method of claim 3 wherein the mammal to be protected is livestock.
11. The method of claim 3 wherein the mammal to be protected is a canine.
12. The method of claim 3 wherein the mammal to be protected is a feline.
13. The method according to claim 3, wherein the isoxazoline-substituted benzamide compounds, an optically active form or the salt thereof are according to a formula
Figure US20150105398A1-20150416-C00096
wherein,
(X)m is 3,5-Cl2, 3-Br, 3-I, 4-I, 3-CF3, 3-OCF3, 3,5-F2, 3,5-Br2, 3,5-(CF3)2, 3,4-Cl2 or 3,5-Cl2-4-CH3,
Y is H, CH3, Br, CH2CH3, Cl, I or OCF3,
R1 is CH(CH3)CH2OCH3, 2-tetrahydrofuryl, CH2CF3, CH2 (2-pyridyl), cyclobutyl, CH2CH2OCH2CH3, tetrahydrofurfuryl, CH2CH2SCH2CH3, CH2CH(CH3)S(O)CH3, CH2CH(CH3)SO2CH3, CH2C(O)NHCH3, CH2C(O)N(CH3)2, CH2C(O)NHCH2CH3, CH2C(O)NHPr-i, CH2C(O)NHCH2CH2Cl, CH2C(O)NHCH2CF3, CH2C(O)NHCH2CH═CH2, CH2C(O)N(CH3)CH2CH═CH2, CH2C(O)NHCH2C═CH, CH(CH3)C(O)NHCH2CH2Cl, CH2(4-trifluoromethylthiazol-2-yl), CH2(4-thiazolyl), CH2(2-chlorothiazol-5-yl), CH2(2-pyridyl), CH(CH3)(2-pyridyl), CH2(4-chloropyridin-2-yl), CH2(6-chloropyridin-2-yl), CH2(3-pyridyl), CH2(2-chloropyridin-5-yl), CH2CH2OCH3, CH2CH2CF3, CH(CF3)OCH3, CH(CH3)C(O)NHCH2CF3, CH(CH3)(2-thiazolyl), CH2OCH3, CH2OCH2CH3, CH2OCH2CH2CH3, CH2OCH(CH3)2, CH2OCH2CH2Cl, CH2OCH2CHF2, CH2OCH2CF3, CH(CH3)OH, 3-tetrahydrofuryl(R),2-tetrahydropyranyl, CH2SCH3, CH2S(O)CH3, CH2SO2CH3, CH2(2-methylthiothiazol-4-yl), 6-methoxy-2-tetrahydropyranyl or CH2(4-pyridyl),
R2 is H, CH3, CH2CF3, C(O)CH3, C(O)CH2CH3, C(O)OCH3, C(O)OBu-i, C(O)OCH2CH2Cl, CH2CH3, cyclopropyl, CH2OCH2CH3 or CH2OCH3, and
R3 is CF3, CHF2, CF2Cl or CF2CF3.
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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10653136B2 (en) 2016-07-11 2020-05-19 Covestro Llc Aqueous compositions for treating seeds, seeds treated therewith, and methods for treating seeds
US10653135B2 (en) 2016-07-11 2020-05-19 Covestro Llc Methods for treating seeds with an aqueous composition and seeds treated therewith
US10750750B2 (en) 2016-07-11 2020-08-25 Covestro Llc Aqueous compositions for treating seeds, seeds treated therewith, and methods for treating seeds

Families Citing this family (545)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1930136B (en) 2004-03-05 2012-02-08 日产化学工业株式会社 Isoxazoline-substituted benzamide compound and noxious organism control agent
TW200613272A (en) 2004-08-13 2006-05-01 Astrazeneca Ab Isoindolone compounds and their use as metabotropic glutamate receptor potentiators
US7868008B2 (en) 2005-08-12 2011-01-11 Astrazeneca Ab Substituted isoindolones and their use as metabotropic glutamate receptor potentiators
WO2007021309A1 (en) * 2005-08-12 2007-02-22 Astrazeneca Ab Substituted isoindolones and their use as metabotropic glutamate receptor potentiators
US7807706B2 (en) 2005-08-12 2010-10-05 Astrazeneca Ab Metabotropic glutamate-receptor-potentiating isoindolones
US20100016298A1 (en) * 2005-08-29 2010-01-21 Housey Gerad M Theramutein modulators
ES2443690T3 (en) * 2005-09-02 2014-02-20 Nissan Chemical Industries, Ltd. Isoxazoline-substituted benzamide compound and harmful agent controlling agent
JP5186751B2 (en) * 2005-10-14 2013-04-24 住友化学株式会社 Hydrazide compounds and their pest control applications
JP2009512660A (en) * 2005-10-21 2009-03-26 ビーエーエスエフ ソシエタス・ヨーロピア Isothiazolopyridin-3-ylenamines for controlling pests
EP1965645A2 (en) * 2005-12-14 2008-09-10 E.I. Du Pont De Nemours And Company Isoxazolines for controlling invertebrate pests
TW200803740A (en) * 2005-12-16 2008-01-16 Du Pont 5-aryl isoxazolines for controlling invertebrate pests
CN101331127B (en) * 2005-12-16 2012-05-23 杜邦公司 5-aryl isoxazolines for controlling invertebrate pests
FR2895605A1 (en) * 2005-12-22 2007-06-29 Thomson Licensing Sas METHOD FOR RECEIVING MULTIPLE CARRIER SIGNAL, TRANSMITTING METHOD, RECEIVER AND TRANSMITTER THEREFOR
US7700808B2 (en) 2005-12-26 2010-04-20 Nissan Chemical Industries, Ltd. 1-3-bis(substituted phenyl)-3-hydroxypropan-1-one or 2-propen-1-one compound, and salt thereof
TWI412322B (en) * 2005-12-30 2013-10-21 Du Pont Isoxazolines for controlling invertebrate pests
WO2007094313A1 (en) * 2006-02-13 2007-08-23 Nissan Chemical Industries, Ltd. Process for production of 2-(substituted phenyl)-3,3,3-trifluoropropene compound
DE602007006288D1 (en) 2006-03-10 2010-06-17 Nissan Chemical Ind Ltd SUBSTITUTED ISOXAZOLIN COMPOUND AND PESTICIDES
US20070238700A1 (en) * 2006-04-10 2007-10-11 Winzenberg Kevin N N-phenyl-1,1,1-trifluoromethanesulfonamide hydrazone derivative compounds and their usage in controlling parasites
AU2007240954A1 (en) * 2006-04-20 2007-11-01 E. I. Du Pont De Nemours And Company Pyrazolines for controlling invertebrate pests
JPWO2007125984A1 (en) * 2006-04-28 2009-09-10 日本農薬株式会社 Isoxazoline derivatives, pest control agents and methods of use
JP2008044880A (en) 2006-08-15 2008-02-28 Bayer Cropscience Ag Insecticidal isooxazolines
JP5164510B2 (en) * 2006-10-06 2013-03-21 日本曹達株式会社 Nitrogen-containing heterocyclic compounds and pest control agents
JP2009062352A (en) * 2006-10-12 2009-03-26 Nippon Soda Co Ltd Nitrogen-containing heterocyclic compound and pest control agent
JP5164525B2 (en) * 2006-11-01 2013-03-21 日本曹達株式会社 Nitrogen-containing heterocyclic compounds and pest control agents
WO2008108448A1 (en) 2007-03-07 2008-09-12 Nissan Chemical Industries, Ltd. Isoxazoline-substituted benzamide compound and pest control agent
JP5256753B2 (en) * 2007-03-29 2013-08-07 住友化学株式会社 Isoxazoline compounds and their pest control applications
NZ580241A (en) * 2007-04-10 2011-02-25 Bayer Cropscience Ag Insecticidal aryl isoxazoline derivatives
JP2008260691A (en) * 2007-04-10 2008-10-30 Bayer Cropscience Ag Insecticidal arylisoxazoline derivative
WO2008130651A2 (en) * 2007-04-20 2008-10-30 Dow Agrosciences Llc Diarylisoxazolines
JP2008266230A (en) * 2007-04-23 2008-11-06 Bayer Cropscience Ag Insecticidal arylpyrrolidines
JP2010116389A (en) * 2008-10-17 2010-05-27 Bayer Cropscience Ag Insecticidal arylpyrrolidines
US9266830B2 (en) 2007-04-23 2016-02-23 Bayer Intellectual Property Gmbh Pesticidal arylpyrrolidines
TWI417100B (en) 2007-06-07 2013-12-01 Astrazeneca Ab Oxadiazole derivatives and their use as metabotropic glutamate receptor potentiators-842
AU2014277839B2 (en) * 2007-06-13 2017-02-02 Corteva Agriscience Llc Isoxazoline insecticides
AU2008261793A1 (en) * 2007-06-13 2008-12-18 E. I. Du Pont De Nemours And Company Isoxazoline insecticides
AU2016208330A1 (en) * 2007-06-26 2016-08-11 E. I. Du Pont De Nemours And Company Naphthalene isoxazoline invertebrate pest control agents
AU2013273726B2 (en) * 2007-06-26 2016-04-28 Corteva Agriscience Llc Naphthalene isoxazoline invertebrate pest control agents
TWI430995B (en) * 2007-06-26 2014-03-21 Du Pont Naphthalene isoxazoline invertebrate pest control agents
AU2014259503C1 (en) * 2007-06-27 2019-06-13 E. I. Du Pont De Nemours And Company Animal pest control method
MX361762B (en) * 2007-06-27 2018-12-17 Du Pont Animal pest control method.
US8952175B2 (en) * 2007-06-27 2015-02-10 Nissan Chemical Industries, Ltd. Method for production of 3-hydroxypropan-1-one compound, method for production of 2-propen-1-one compound and method for production of isoxazoline compound
WO2009005015A1 (en) 2007-06-29 2009-01-08 Nissan Chemical Industries, Ltd. Substituted isoxazoline or enone oxime compound, and pest control agent
JP5184057B2 (en) * 2007-08-10 2013-04-17 日本曹達株式会社 Nitrogen-containing heterocyclic compounds and pest control agents
JP5128600B2 (en) * 2007-08-10 2013-01-23 日本曹達株式会社 Nitrogen-containing heterocyclic compounds and pest control agents
AU2020230282B2 (en) * 2007-08-17 2022-04-07 Intervet International B.V. Isoxazoline compositions and their use as antiparasitics
TWI649303B (en) * 2007-08-17 2019-02-01 杜邦股份有限公司 Compound and method for preparing 4-acetyl-n-[2-oxo-2-[(2,2,2-trifluoroethyl)amino]ethyl]-1-naphthalenecarboxamide
TWI556741B (en) * 2007-08-17 2016-11-11 英特威特國際股份有限公司 Isoxazoline compositions and their use as antiparasitics
CA2696609C (en) * 2007-08-27 2017-09-05 Helicon Therapeutics, Inc. Therapeutic isoxazole compounds
US8318757B2 (en) 2007-09-10 2012-11-27 Nissan Chemical Industries, Ltd. Substituted isoxazoline compound and pest control agent
JP5173335B2 (en) * 2007-09-13 2013-04-03 東ソ−・エフテック株式会社 Process for producing (1-perfluoroalkyl) vinylaryls
US8367584B2 (en) 2007-10-03 2013-02-05 E.I. Du Pont De Nemours And Company Naphthalene isoxazoline compounds for control of invertebrate pests
GB0720232D0 (en) 2007-10-16 2007-11-28 Syngenta Participations Ag Insecticidal compounds
WO2009063910A1 (en) * 2007-11-12 2009-05-22 Nissan Chemical Industries, Ltd. Method for catalytic asymmetric synthesis of optically active isoxazoline compound
TWI356094B (en) * 2007-11-14 2012-01-11 Ind Tech Res Inst Liquid crystal compound and liquid crystal display
EP2230230A4 (en) 2007-12-07 2011-03-16 Nissan Chemical Ind Ltd Substituted dihydroazole compound and pest control agent
AU2008337876A1 (en) 2007-12-19 2009-06-25 Syngenta Participations Ag Insecticidal compounds
JP5324082B2 (en) * 2007-12-20 2013-10-23 大阪瓦斯株式会社 Process for producing 9,9-bis (carboxyaryl) fluorenes and esters thereof
TWI411395B (en) * 2007-12-24 2013-10-11 Syngenta Participations Ag Insecticidal compounds
US8304371B2 (en) 2008-02-07 2012-11-06 Bayer Cropscience Ag Insecticidal arylpyrrolines
JP2009286773A (en) * 2008-03-14 2009-12-10 Bayer Cropscience Ag Insecticidal condensed-ring aryl compounds
TWI583664B (en) * 2008-04-09 2017-05-21 杜邦股份有限公司 Carbonyl compound and method for preparing thereof
SA109300358B1 (en) 2008-06-06 2012-11-03 استرازينيكا ايه بي Isoindolone Metabotropic Glutamate receptor Potentiators
JP2011527307A (en) 2008-07-09 2011-10-27 ビーエーエスエフ ソシエタス・ヨーロピア Pesticide active mixture comprising isoxazoline compound I
AU2009270255B2 (en) 2008-07-09 2013-12-12 Nissan Chemical Corporation Process for production of isoxazoline-substituted benzoic acid amide compound
AU2014200736B2 (en) * 2008-07-09 2015-08-20 Nissan Chemical Corporation Process for production of isoxazoline-substituted benzoic acid amide compound
KR20110028538A (en) * 2008-07-09 2011-03-18 바스프 에스이 Pesticidal mixtures comprising isoxazoline compounds ii
MX2011001851A (en) * 2008-08-22 2011-03-21 Syngenta Participations Ag Insceticidal compounds.
BRPI0917369A2 (en) * 2008-08-22 2015-08-04 Syngenta Participations Ag Insecticide Compounds
JP5488835B2 (en) * 2008-09-04 2014-05-14 日産化学工業株式会社 Substituted acetophenone compound, method for producing the same, and use thereof
JP2012501989A (en) 2008-09-04 2012-01-26 シンジェンタ パーティシペーションズ アクチェンゲゼルシャフト Insecticidal compound
CA2737291C (en) 2008-09-18 2013-04-16 Nippon Soda Co., Ltd. Nitrogen-containing heterocyclic compound and pest control agent
EP3498696A1 (en) 2008-11-14 2019-06-19 Merial, Inc. Enantiomerically enriched aryloazol-2-yl cyanoethylamino parasiticidal compounds
KR101660068B1 (en) 2008-11-19 2016-09-26 메리얼 인코포레이티드 Compositions comprising 1-arylpyrazole alone or in combination with formamidine for the treatment of parasitic infection
US8426460B2 (en) 2008-12-04 2013-04-23 Merial Limited Dimeric avermectin and milbemycin derivatives
JP5715065B2 (en) * 2008-12-23 2015-05-07 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ Substituted amidine compounds for combating harmful animals
WO2010072781A2 (en) * 2008-12-23 2010-07-01 Basf Se Imine compounds for combating invertebrate pests
US20110288089A1 (en) 2009-01-22 2011-11-24 Syngenta Crop Protection Llc Insecticidal compounds
US20110288131A1 (en) 2009-01-29 2011-11-24 Syngenta Crop Protection Llc Insecticidal compounds
JP5747440B2 (en) 2009-02-06 2015-07-15 住友化学株式会社 Hydrazide compound and its use for pest control
CN102365278B (en) * 2009-03-26 2015-05-06 先正达参股股份有限公司 Insecticidal compounds
WO2010112545A1 (en) 2009-04-01 2010-10-07 Basf Se Isoxazoline compounds for combating invertebrate pests
WO2010129345A2 (en) 2009-04-28 2010-11-11 Basf Corporation Foamable pesticide compositions
EP2424862B1 (en) 2009-04-30 2014-10-08 Basf Se Process for preparing substituted isoxazoline compounds and their precursors
WO2010133336A1 (en) 2009-05-19 2010-11-25 Bayer Cropscience Ag Insecticidal arylpyrrolines
CA2764422A1 (en) 2009-06-22 2010-12-29 Syngenta Participations Ag Insecticidal compounds
CN102469785A (en) 2009-07-24 2012-05-23 巴斯夫欧洲公司 pyridine derivatives for controlling invertebrate pests
ES2545738T3 (en) 2009-07-30 2015-09-15 Merial, Inc. Insecticidal compounds based on 4-amino-thieno [2,3-d] -pyrimidine and procedures for its use
JP5679102B2 (en) * 2009-08-03 2015-03-04 日産化学工業株式会社 Optically active form and diastereomeric salt of dihydroisoxazole-substituted benzoic acid compound and method for producing the same
AU2010279377B2 (en) * 2009-08-07 2014-07-03 Dow Agrosciences Llc Pesticidal compositions
UA108619C2 (en) * 2009-08-07 2015-05-25 PESTICIDIC COMPOSITIONS
JP2011057661A (en) * 2009-08-14 2011-03-24 Bayer Cropscience Ag Pesticidal carboxamides
MX2012002308A (en) 2009-08-28 2012-03-29 Basf Corp Foamable pesticide compositions and methods of application.
BR112012006615A2 (en) 2009-09-24 2019-09-24 Basf Se amnoquinazoline compounds of formula I, agricultural composition, veterinary composition, plant propagation material method, seeds and use
JP2011093855A (en) 2009-10-30 2011-05-12 Bayer Cropscience Ag Insecticidal oxazolidinone derivative
WO2011057942A1 (en) 2009-11-12 2011-05-19 Basf Se Insecticidal methods using pyridine compounds
MX2012005612A (en) 2009-11-17 2012-11-30 Merial Ltd Fluorinated oxa or thia heteroarylalkylsulfide derivatives for combating invertebrate pests.
WO2011064188A1 (en) 2009-11-27 2011-06-03 Basf Se Insecticidal methods using nitrogen-containing heteroaromatic compounds
TWI487486B (en) * 2009-12-01 2015-06-11 Syngenta Participations Ag Insecticidal compounds based on isoxazoline derivatives
MX2012006366A (en) 2009-12-04 2012-06-27 Basf Se Pesticidal bis-organosulfur compounds.
WO2011069955A1 (en) 2009-12-07 2011-06-16 Basf Se Sulfonimidamide compounds for combating animal pests
NZ600922A (en) 2009-12-17 2013-10-25 Merial Ltd Anti parasitic dihydroazole compounds and compositions comprising same
BR112012014944A2 (en) 2009-12-18 2015-09-15 Basf Se substituted azoline compounds, composition, use of a compound, and methods for controlling invertebrate pests and for treating, controlling, preventing or protecting animals against infestation or parasite infection.
JP2011136928A (en) 2009-12-28 2011-07-14 Bayer Cropscience Ag Insecticidal arylpyrrolidines
EP2531493B1 (en) 2010-02-01 2015-07-22 Basf Se Substituted ketonic isoxazoline compounds and derivatives for combating animal pests
AU2011212478B2 (en) 2010-02-05 2014-11-06 Intervet International B.V. Spiroindoline Compounds For Use as Anthelminthics
WO2011101402A1 (en) 2010-02-17 2011-08-25 Syngenta Participations Ag Isoxazoline derivatives as insecticides
AP2012006432A0 (en) * 2010-02-22 2012-08-31 Syngenta Participations Ag Dihydrofuran derivatives as insecticidal compounds
EP2542533B1 (en) 2010-03-04 2014-09-10 Bayer Intellectual Property GmbH Fluoralkyl-substituted 2-amidobenzimidazoles and their use for increasing stress tolerance in plants
WO2011117804A1 (en) 2010-03-23 2011-09-29 Basf Se Pyridazine compounds for controlling invertebrate pests
EP2550261B1 (en) 2010-03-23 2016-03-16 Basf Se Pyridazine compounds for controlling invertebrate pests
UA108641C2 (en) 2010-04-02 2015-05-25 PARASITICID COMPOSITION CONTAINING FOUR ACTIVE AGENTS AND METHOD OF APPLICATION
EP2556060A1 (en) 2010-04-08 2013-02-13 Ah Usa 42 Llc Substituted 3,5- diphenyl-isoxazoline derivatives as insecticides and acaricides
EP2566865B1 (en) 2010-05-05 2014-06-25 Bayer Intellectual Property GmbH Thiazole derivatives as pest controller
CN103025161A (en) 2010-05-24 2013-04-03 明治制果药业株式会社 Noxious organism control agent
US8598087B2 (en) 2010-05-27 2013-12-03 E. I. Du Pont De Nemours And Company Crystalline form of 4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-4, 5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-[2-0X0-2-[(2,2,2-trifluoroethyl)amino]ethyl]-1- naph-thalenecarboxamide
JP5948320B2 (en) 2010-05-28 2016-07-06 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ Pesticide mixture
BR112012031088A8 (en) 2010-06-09 2017-10-10 Syngenta Participations Ag PESTICIDE MIXTURES INCLUDING ISOXAZOLINE DERIVATIVES
US20130203591A1 (en) 2010-06-09 2013-08-08 Syngenta Crop Protection Llc Pesticidal mixtures including isoxazoline derivatives
UY33403A (en) * 2010-06-17 2011-12-30 Novartis Ag ORGANIC COMPOUNDS WITH NEW ISOXAZOLINES, THEIR N-OXIDES, S-OXIDES AND SALTS
DK178277B1 (en) 2010-06-18 2015-10-26 Novartis Tiergesundheit Ag Diaryloxazoline compounds for the control of fish lice
US9198424B2 (en) 2010-06-18 2015-12-01 Bayer Intellectual Property Gmbh Active ingredient combinations having insecticidal and acaricidal properties
US9085541B2 (en) 2010-06-23 2015-07-21 Basf Se Process for producing imine compounds for combating invertebrate pests
CN103119036B (en) 2010-06-28 2018-05-08 拜耳知识产权有限责任公司 Heterocyclic compound as insecticide
WO2012004293A2 (en) 2010-07-08 2012-01-12 Bayer Cropscience Ag Insecticide and fungicide active ingredient combinations
JP2012017289A (en) 2010-07-08 2012-01-26 Bayer Cropscience Ag Pesticidal pyrroline derivative
WO2012007426A1 (en) 2010-07-13 2012-01-19 Basf Se Azoline substituted isoxazoline benzamide compounds for combating animal pests
CN103003263B (en) 2010-07-22 2015-07-22 巴斯夫欧洲公司 Novel hetaryl (thio)carboxamide compounds for controlling invertebrate pests
CN103097376A (en) 2010-09-13 2013-05-08 巴斯夫欧洲公司 Pyridine compounds for controlling invertebrate pests ii
US20130180014A1 (en) 2010-09-13 2013-07-11 Basf Se Pyridine Compounds for Controlling Invertebrate Pests III
EP2616459B1 (en) 2010-09-13 2016-05-04 Basf Se Pyridine compounds for controlling invertebrate pests i
JP2012082186A (en) 2010-09-15 2012-04-26 Bayer Cropscience Ag Insecticidal arylpyrrolidines
JP2012062267A (en) 2010-09-15 2012-03-29 Bayer Cropscience Ag Pesticidal pyrroline n-oxide derivative
WO2012038851A1 (en) 2010-09-24 2012-03-29 Pfizer Inc. Isoxazoline oximes as antiparasitic agents
WO2012041873A1 (en) 2010-09-29 2012-04-05 Intervet International B.V. N-heteroaryl compounds
WO2012041872A1 (en) 2010-09-29 2012-04-05 Intervet International B.V. N-heteroaryl compounds with cyclic bridging unit for the treatment of parasitic diseases
EP2621897A1 (en) 2010-10-01 2013-08-07 Basf Se Imine compounds
US8653000B2 (en) 2010-10-01 2014-02-18 Basf Se Imine substituted 2,4-diaryl-pyrroline derivatives as pesticides
WO2012045680A2 (en) 2010-10-04 2012-04-12 Bayer Cropscience Ag Insecticidal and fungicidal active substance combinations
BR112013009580B1 (en) 2010-10-21 2018-06-19 Bayer Intellectual Property Gmbh FORMULA COMPOUND (I), FUNGICIDE COMPOSITION AND METHOD FOR CONTROLING PHYTOPATHOGENIC FUNGES
BR112013010683B1 (en) 2010-11-02 2018-06-26 Bayer Intellectual Property Gmbh COMPOUND, FUNGICIDE COMPOSITION AND METHOD FOR CONTROLLING PHYTOPATHOGENIC CROP FUNGI
WO2012059441A2 (en) 2010-11-03 2012-05-10 Basf Se Method for preparing substituted isoxazoline compounds and their precursors 4-chloro, 4-bromo- or 4-iodobenzaldehyde oximes
JP2014015397A (en) * 2010-11-04 2014-01-30 Nippon Soda Co Ltd External parasite controlling agent for animals
WO2012065944A1 (en) 2010-11-15 2012-05-24 Bayer Cropscience Ag N-aryl pyrazole(thio)carboxamides
JP2014028758A (en) 2010-11-19 2014-02-13 Nissan Chem Ind Ltd Agent for controlling parasite and sanitary insect pest
BR112013012966A2 (en) 2010-11-29 2016-08-23 Bayer Ip Gmbh alpha, beta imines - unsaturated
CN107396929A (en) 2010-12-01 2017-11-28 拜耳知识产权有限责任公司 Fluopyram is used to prevent and treat the nematode in crop and improves the purposes of yield
US20130253012A1 (en) 2010-12-10 2013-09-26 Basf Se Pyrazole Compounds for Controlling Invertebrate Pests
TWI667347B (en) 2010-12-15 2019-08-01 瑞士商先正達合夥公司 Soybean event syht0h2 and compositions and methods for detection thereof
BR112013014913A2 (en) 2010-12-20 2016-07-19 Basf Se pesticide mixtures, pesticidal or parasiticidal composition, method to protect vegetables from insect attack or infestation, to control insects, to control harmful phytopathogenic fungi, to protect vegetables from harmful phytopathogenic fungi, to protect material propagation of plants, for the protection of animals against parasitic infestation or infection, for the treatment of parasites infected or infected with
DE102010063691A1 (en) 2010-12-21 2012-06-21 Bayer Animal Health Gmbh Ectoparasiticidal drug combinations
WO2012085081A1 (en) 2010-12-22 2012-06-28 Basf Se Sulfoximinamide compounds for combating invertebrate pests ii
HUE058290T2 (en) 2010-12-27 2022-07-28 Intervet Int Bv Topical localized isoxazoline formulation comprising glycofurol
DK2658542T3 (en) 2010-12-27 2022-03-28 Intervet Int Bv TOPIC LOCALIZED ISOXAZOLE INFORMATION
EP2471363A1 (en) 2010-12-30 2012-07-04 Bayer CropScience AG Use of aryl-, heteroaryl- and benzylsulfonamide carboxylic acids, -carboxylic acid esters, -carboxylic acid amides and -carbonitriles and/or its salts for increasing stress tolerance in plants
UY33887A (en) * 2011-02-03 2012-09-28 Syngenta Ltd PEST CONTROL METHODS IN SOYA
US9510594B2 (en) 2011-02-17 2016-12-06 Bayer Intellectual Property Gmbh Use of SDHI fungicides on conventionally bred ASR-tolerant, stem canker resistant and/or frog-eye leaf spot resistant soybean varieties
US9000026B2 (en) 2011-02-17 2015-04-07 Bayer Intellectual Property Gmbh Substituted 3-(biphenyl-3-yl)-8,8-difluoro-4-hydroxy-1-azaspiro[4.5]dec-3-en-2-ones for therapy
WO2012110464A1 (en) 2011-02-17 2012-08-23 Bayer Cropscience Ag Use of sdhi fungicides on conventionally bred asr-tolerant, stem canker resistant and/or frog-eye leaf spot resistant soybean varieties
ES2550391T3 (en) 2011-03-01 2015-11-06 Bayer Intellectual Property Gmbh 2-Acyloxy-pyrrolin-4-ones
AR085509A1 (en) 2011-03-09 2013-10-09 Bayer Cropscience Ag INDOL- AND BENCIMIDAZOLCARBOXAMIDS AS INSECTICIDES AND ACARICIDES
BR112013022998A2 (en) 2011-03-10 2018-07-03 Bayer Ip Gmbh method to improve seed germination.
SI2683723T1 (en) * 2011-03-10 2016-07-29 Zoetis Services Llc Spirocyclic isoxazoline derivatives as antiparasitic agents
CN103502221B (en) 2011-03-18 2016-03-30 拜耳知识产权有限责任公司 N- (3-carbamoylphenyl) -1H-pyrazole-5-carboxamide derivatives and their use for controlling animal pests
EP2694502A1 (en) 2011-04-06 2014-02-12 Basf Se Substituted pyrimidinium compounds for combating animal pests
AR085872A1 (en) 2011-04-08 2013-10-30 Basf Se HETEROBICICLIC DERIVATIVES N-SUBSTITUTES USEFUL TO COMBAT PARASITES IN PLANTS AND / OR ANIMALS, COMPOSITIONS THAT CONTAIN THEM AND METHODS TO COMBAT SUCH PESTS
AR085585A1 (en) 2011-04-15 2013-10-09 Bayer Cropscience Ag VINIL- AND ALQUINILCICLOHEXANOLES SUBSTITUTED AS ACTIVE PRINCIPLES AGAINST STRIPS ABIOTIQUE OF PLANTS
AR090010A1 (en) 2011-04-15 2014-10-15 Bayer Cropscience Ag 5- (CICLOHEX-2-EN-1-IL) -PENTA-2,4-DIENOS AND 5- (CICLOHEX-2-EN-1-IL) -PENT-2-EN-4-INOS REPLACED AS ACTIVE PRINCIPLES AGAINST THE ABIOTIC STRESS OF PLANTS, USES AND TREATMENT METHODS
AR085568A1 (en) 2011-04-15 2013-10-09 Bayer Cropscience Ag 5- (BICYCLE [4.1.0] HEPT-3-EN-2-IL) -PENTA-2,4-DIENOS AND 5- (BICYCLE [4.1.0] HEPT-3-EN-2-IL) -PENT- 2-IN-4-INOS REPLACED AS ACTIVE PRINCIPLES AGAINST ABIOTIC STRESS OF PLANTS
CN103492378B (en) 2011-04-21 2016-09-28 巴斯夫欧洲公司 Parasite killing pyrazole compound
AR086113A1 (en) 2011-04-30 2013-11-20 Abbott Lab ISOXAZOLINS AS THERAPEUTIC AGENTS
MX361350B (en) 2011-05-10 2018-12-04 Gilead Sciences Inc Fused heterocyclic compounds as sodium channel modulators.
MX2013013211A (en) * 2011-05-18 2014-02-20 Syngenta Participations Ag Insecticidal compounds based on arylthioacetamide derivatives.
WO2012155352A1 (en) * 2011-05-19 2012-11-22 Eli Lilly And Company Dihydroisoxazole compounds, parasiticidal uses and formulations thereof
AR086588A1 (en) * 2011-05-31 2014-01-08 Syngenta Participations Ag PESTICIDE MIXTURES THAT INCLUDE ISOXAZOLINIC DERIVATIVES
UA113287C2 (en) * 2011-05-31 2017-01-10 PESTICIDIC MIXTURES CONTAINING ISOXASOLINE DERIVATIVES
WO2012163948A1 (en) 2011-05-31 2012-12-06 Syngenta Participations Ag Pesticidal mixtures including isoxazoline derivatives
UY34104A (en) 2011-05-31 2013-01-03 Syngenta Participations Ag ? HETEROCYCLIC BENZAMID DERIVATIVE COMPOUNDS, PROCESSES AND INTERMEDIATES FOR PREPARATION, COMPOSITIONS AND METHODS FOR USE.
EP2535334A1 (en) 2011-06-17 2012-12-19 Bayer CropScience AG Crystalline modifications of penflufen
AU2012272999B2 (en) * 2011-06-24 2016-05-19 Dow Agrosciences Llc Pesticidal compositions and processes related thereto
AU2012275435B2 (en) 2011-06-27 2016-07-21 Boehringer Ingelheim Animal Health USA Inc. Amido-pyridyl ether compounds and compositions and their use against parasites
EP2540163A1 (en) 2011-06-30 2013-01-02 Bayer CropScience AG Nematocide N-cyclopropyl-sulfonylamide derivatives
TWI622583B (en) 2011-07-01 2018-05-01 基利科學股份有限公司 Fused heterocyclic compounds as ion channel modulators
NO3175985T3 (en) 2011-07-01 2018-04-28
CN103957711A (en) 2011-07-04 2014-07-30 拜耳知识产权有限责任公司 Use of substituted isoquinolinones, isoquinolindiones, isoquinolintriones and dihydroisoquinolinones or in each case salts thereof as active agents against abiotic stress in plants
AR087119A1 (en) * 2011-07-12 2014-02-12 Dow Agrosciences Llc PESTICIATED COMPOSITIONS AND RELATED PROCESSES
MX2014000514A (en) 2011-07-15 2014-02-19 Basf Se Pesticidal methods using substituted 3-pyridyl thiazole compounds and derivatives for combating animal pests i.
CA2843048A1 (en) 2011-07-26 2013-01-31 Bayer Intellectual Property Gmbh Etherified lactate esters, method for the production thereof and use thereof for enhancing the effect of plant protecting agents
EP2736333A1 (en) 2011-07-27 2014-06-04 Bayer Intellectual Property GmbH Seed dressing for controlling phytopathogenic fungi
US9096599B2 (en) 2011-08-04 2015-08-04 Intervet Inc. Spiroindoline compounds
CA2843083A1 (en) * 2011-08-12 2013-02-21 Basf Se Anthranilamide compounds and their use as pesticides
AR087516A1 (en) 2011-08-12 2014-03-26 Basf Se N-TIO-ANTRANILAMIDE COMPOUNDS AND THEIR USES AS PESTICIDES
AR088786A1 (en) 2011-08-12 2014-07-10 Basf Se ANTRANILAMIDE COMPOUNDS AND THEIR USES AS PESTICIDES
JP2014522872A (en) 2011-08-12 2014-09-08 ビーエーエスエフ ソシエタス・ヨーロピア N-thio-anthranilamide compounds and their use as pesticides
BR112014003186A2 (en) 2011-08-12 2017-04-04 Basf Se compound of general formula (i), pesticide combination, agricultural or veterinary composition, method for combating or controlling invertebrate pests, method for protecting plants and seeds, seed, use of a compound and method for treating an animal
EP2742027A1 (en) 2011-08-12 2014-06-18 Basf Se N-thio-anthranilamide compounds and their use as pesticides
EA201400213A1 (en) 2011-08-12 2014-08-29 Басф Се CONNECTIONS OF ANILINE TYPE
EP2744784A1 (en) 2011-08-18 2014-06-25 Basf Se Carbamoylmethoxy- and carbamoylmethylthio- and carbamoylmethylamino benzamides for combating invertebrate pests
EP2744785A1 (en) 2011-08-18 2014-06-25 Basf Se Carbamoylmethoxy- and carbamoylmethylthio- and carbamoylmethylamino benzamides for combating invertebrate pests
JP2014524432A (en) 2011-08-18 2014-09-22 ビーエーエスエフ ソシエタス・ヨーロピア Carbamoylmethoxybenzamide and carbamoylmethylthiobenzamide and carbamoylmethylaminobenzamide for combating harmful invertebrates
US20140343049A1 (en) 2011-08-22 2014-11-20 Syngenta Participations Ag Dihydrofuran derivatives as insecticidal compounds
CN103732567A (en) 2011-08-22 2014-04-16 先正达参股股份有限公司 Dihydrofuran derivatives as insecticidal compounds
WO2013026695A1 (en) 2011-08-25 2013-02-28 Syngenta Participations Ag Isoxazoline derivatives as insecticidal compounds
JP2014524459A (en) * 2011-08-25 2014-09-22 シンジェンタ パーティシペーションズ アクチェンゲゼルシャフト Termites and ant control methods
JP6061934B2 (en) * 2011-08-25 2017-01-18 シンジェンタ パーティシペーションズ アーゲー Isoxazoline derivatives as insecticidal compounds
EP2561759A1 (en) 2011-08-26 2013-02-27 Bayer Cropscience AG Fluoroalkyl-substituted 2-amidobenzimidazoles and their effect on plant growth
US20140213445A1 (en) 2011-09-02 2014-07-31 Basf Se Use of Pesticidal Active 3-Arylquinazolin-4-One Derivatives in Soil Application Methods
EP2750503A1 (en) 2011-09-02 2014-07-09 Basf Se Insecticidal active mixtures comprising arylquinazolinone compounds
KR102081036B1 (en) 2011-09-12 2020-02-24 뵈링거 잉겔하임 애니멀 헬스 유에스에이 인코포레이티드 Parasiticidal compositions comprising an isoxazoline active agent, methods and uses thereof
EP3190110B1 (en) 2011-09-13 2020-01-08 Syngenta Participations AG Isothiazoline derivatives as insecticidal compounds
AU2012307324A1 (en) 2011-09-16 2014-03-06 Bayer Intellectual Property Gmbh Use of phenylpyrazolin-3-carboxylates for improving plant yield
UA113967C2 (en) 2011-09-16 2017-04-10 APPLICATION OF 5-PHENYL OR 5-BENZYL-2-ISOXAZOLINE-3-CARBOXYLATES TO IMPROVE PLANT PRODUCTIVITY
AR087874A1 (en) 2011-09-16 2014-04-23 Bayer Ip Gmbh USE OF ACILSULPHONAMIDES TO IMPROVE THE PERFORMANCE OF PLANTS
JP2013082632A (en) 2011-10-05 2013-05-09 Bayer Cropscience Ag Agrochemical formulation and manufacturing method of the same
CN104271128A (en) 2011-10-19 2015-01-07 佐蒂斯有限责任公司 Use of aminoacetonitrile derivatives against endoparasites
WO2013069731A1 (en) 2011-11-08 2013-05-16 日産化学工業株式会社 Method for catalytic asymmetric synthesis of optically active isoxazoline compound, and optically active isoxazoline compound
CN104023720B (en) 2011-11-17 2016-10-26 梅里亚有限公司 Comprise the compositions of arylpyrazole and substituted imidazole, its method and purposes
AR088669A1 (en) * 2011-11-21 2014-06-25 Lilly Co Eli DERIVATIVES OF DIHYDRODIBENZO [C] [1,2] OXABOROL AND DIHYDROISOXAZOL USEFUL FOR THE CONTROL OF ECTOPARASITES
US20140343085A1 (en) * 2011-11-29 2014-11-20 Novartis Ag Use of aryl derivatives for controlling ectoparasites
WO2013079600A1 (en) 2011-12-02 2013-06-06 Basf Se Method and system for monitoring crops during storage
CN104053660B (en) 2011-12-02 2016-12-28 梅里亚有限公司 Long-acting injectable Moxidectin preparaton and new Moxidectin crystal formation
WO2013079601A1 (en) 2011-12-02 2013-06-06 Basf Se Method and system for monitoring crops and/or infestation of crops with harmful organismus during storage
EP2604118A1 (en) 2011-12-15 2013-06-19 Bayer CropScience AG Active ingredient combinations having insecticidal and acaricidal properties
AU2012357896B9 (en) 2011-12-19 2016-12-15 Bayer Cropscience Ag Use of anthranilic acid diamide derivatives for pest control in transgenic crops
WO2013092522A1 (en) 2011-12-20 2013-06-27 Bayer Intellectual Property Gmbh Novel insecticidal aromatic amides
JP2015502966A (en) 2011-12-21 2015-01-29 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ N-thio-anthranilamide compounds and their use as pesticides
EP2606726A1 (en) 2011-12-21 2013-06-26 Bayer CropScience AG N-Arylamidine-substituted trifluoroethylsulfide derivatives as acaricides and insecticides
ES2727479T3 (en) 2011-12-23 2019-10-16 Basf Se Isothiazoline compounds to fight invertebrate pests
JP6456145B2 (en) 2012-01-21 2019-01-23 バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ Use of host defense inducers to control bacterial harmful microorganisms in useful plants
WO2013113789A1 (en) 2012-02-02 2013-08-08 Basf Se N-thio-anthranilamide compounds and their use as pesticides
DK2811998T3 (en) 2012-02-06 2019-02-25 Merial Inc PARASITICIDE ORAL VETERINARY COMPOSITIONS COMPREHENSIVE SYSTEMIC ACTIVATING ACTIVITIES, PROCEDURES AND APPLICATIONS THEREOF
JO3626B1 (en) 2012-02-23 2020-08-27 Merial Inc Topical compositions comprising fipronil and permethrin and methods of use
WO2013135674A1 (en) 2012-03-12 2013-09-19 Syngenta Participations Ag Insecticidal 2-aryl-acetamide compounds
EP2825532A1 (en) 2012-03-14 2015-01-21 Bayer Intellectual Property GmbH Pesticidal arylpyrrolidines
US9487523B2 (en) 2012-03-14 2016-11-08 Merck Sharp & Dohme Corp. Process for making CGRP receptor antagonists
ES2744597T3 (en) 2012-03-28 2020-02-25 Intervet Int Bv Heteroaryl compounds with an acyclic unit as a bridge
AU2013241854B2 (en) 2012-03-28 2017-11-02 Intervet International B.V. Heteroaryl compounds with cyclic bridging unit for use in the treatment helminth infection
WO2013144228A1 (en) 2012-03-29 2013-10-03 Basf Se Pesticidal methods using heterocyclic compounds and derivatives for combating animal pests
WO2013144223A1 (en) 2012-03-30 2013-10-03 Basf Se N-substituted pyrimidinylidene compounds and derivatives for combating animal pests
CN104202981B (en) 2012-03-30 2018-01-30 巴斯夫欧洲公司 Prevent and treat the pyridylidene compound and derivative of the N substitutions of animal pest
WO2013149940A1 (en) 2012-04-02 2013-10-10 Basf Se Acrylamide compounds for combating invertebrate pests
WO2013149903A1 (en) 2012-04-03 2013-10-10 Basf Se N- substituted hetero - bicyclic furanone derivatives for combating animal
CN109010296A (en) 2012-04-04 2018-12-18 英特维特国际股份有限公司 The Solid oral pharmaceutical composition of isoxazoline compound
WO2013150115A1 (en) 2012-04-05 2013-10-10 Basf Se N- substituted hetero - bicyclic compounds and derivatives for combating animal pests
UA115981C2 (en) 2012-04-20 2018-01-25 Меріал, Інк. Parasiticidal compositions comprising benzimidazole derivatives, methods and uses thereof
MX2014013430A (en) 2012-05-04 2015-04-14 Basf Se Substituted pyrazole-containing compounds and their use as pesticides.
BR112014027133A2 (en) 2012-05-09 2017-06-27 Basf Se compound, agricultural or veterinary composition, method for controlling invertebrate pests, plant propagating material and method for treating or protecting an animal.
MY172146A (en) 2012-05-16 2019-11-14 Bayer Cropscience Ag Insecticidal water-in-oil (w/o) formulation
CN104302173B (en) 2012-05-16 2019-10-15 拜尔农作物科学股份公司 Oil-in-water (O/W) insecticidal preparation
AR091104A1 (en) 2012-05-22 2015-01-14 Bayer Cropscience Ag COMBINATIONS OF ACTIVE COMPOUNDS THAT INCLUDE A LIPO-CHYTOOLIGOSACARIDE DERIVATIVE AND A NEMATICIDE, INSECTICIDE OR FUNGICIDE COMPOUND
MX2014014341A (en) 2012-05-24 2015-07-06 Basf Se N-thio-anthranilamide compounds and their use as pesticides.
IN2014DN09937A (en) 2012-05-30 2015-08-14 Clariant Int Ltd
JP2015519353A (en) 2012-05-30 2015-07-09 バイエル・クロップサイエンス・アーゲーＢａｙｅｒ Ｃｒｏｐｓｃｉｅｎｃｅ Ａｇ Composition containing biological control agent and insecticide
AR091202A1 (en) 2012-05-30 2015-01-21 Bayer Cropscience Ag COMPOSITION THAT INCLUDES A BIOLOGICAL CONTROL AGENT AND AN INSECTICIDE
US10813862B2 (en) 2012-05-30 2020-10-27 Clariant International Ltd. Use of N-methyl-N-acylglucamines as solubilizers
MX2014015265A (en) 2012-06-14 2015-08-12 Basf Se Pesticidal methods using substituted 3-pyridyl thiazole compounds and derivatives for combating animal pests.
CN104703982B (en) 2012-06-20 2018-01-05 巴斯夫欧洲公司 Pyrazole compound and the pesticide combination comprising pyrazole compound
WO2014001120A1 (en) 2012-06-25 2014-01-03 Syngenta Participations Ag Isothiazole derivatives as insecticidal compounds
WO2014001121A1 (en) 2012-06-25 2014-01-03 Syngenta Participations Ag Isothiazole derivatives as insecticidal compounds
WO2014005982A1 (en) 2012-07-05 2014-01-09 Bayer Cropscience Ag Insecticide and fungicide active ingredient combinations
EP2684879A1 (en) 2012-07-09 2014-01-15 Basf Se Substituted mesoionic compounds for combating animal pests
BR112015002176A2 (en) 2012-07-31 2017-07-04 Bayer Cropscience Ag compositions comprising a pesticide mixture of terpene and an insecticide
WO2014019609A1 (en) 2012-07-31 2014-02-06 Syngenta Participations Ag Methods of pest control in soybean
WO2014019957A2 (en) 2012-08-03 2014-02-06 Syngenta Participations Ag Methods of pest control in soybean
CA2878643C (en) 2012-08-03 2021-02-09 Syngenta Participations Ag Methods of pest control in soybean
CN104520287A (en) 2012-08-03 2015-04-15 先正达参股股份有限公司 Methods of controlling insects
IN2015DN01061A (en) 2012-08-17 2015-06-26 Bayer Cropscience Ag
EP2887809B1 (en) 2012-08-24 2018-11-21 Syngenta Participations AG Methods of controlling insects
WO2014029709A1 (en) 2012-08-24 2014-02-27 Syngenta Participations Ag Methods of controlling insects
ES2736314T3 (en) 2012-08-24 2019-12-27 Syngenta Participations Ag Methods to control elaterid worms
EA201590482A1 (en) 2012-09-05 2015-07-30 Байер Кропсайенс Аг APPLICATION OF SUBSTITUTED 2-AMIDOBENZIMIDAZOLES, 2-AMIDOBENZOXAZOLES AND 2-AMIDOBENZOTHIAZOLES OR THEIR SALTS AS A BIOLOGICALLY ACTIVE SUBSTANCE AGAINST THE ABIOTIC STRESS RESISTANCE
BR112015004695A2 (en) * 2012-09-07 2017-07-04 Zoetis Llc spirocyclic isoxazolines as antiparasitic agents
AU2013312896A1 (en) * 2012-09-07 2015-02-26 Zoetis Services Llc Spirocyclic derivatives as antiparasitic agents
US20150230470A1 (en) 2012-09-21 2015-08-20 Basf Se Pyrethroid Insecticide For Protecting Plants And Seed
US10104892B2 (en) * 2012-09-25 2018-10-23 Bayer Cropscience Ag Herbicidally and fungicidally active 3-heteroaryl-isoxazoline-5-carboxamides and 3-heteroaryl-isoxazoline-5-thioamides
WO2014053395A1 (en) 2012-10-01 2014-04-10 Basf Se Use of n-thio-anthranilamide compounds on cultivated plants
WO2014053407A1 (en) 2012-10-01 2014-04-10 Basf Se N-thio-anthranilamide compounds and their use as pesticides
US20150237858A1 (en) 2012-10-01 2015-08-27 Basf Se Method of controlling ryanodine-modulator insecticide resistant insects
WO2014053401A2 (en) 2012-10-01 2014-04-10 Basf Se Method of improving plant health
CN104968201A (en) 2012-10-01 2015-10-07 巴斯夫欧洲公司 Pesticidally active mixtures comprising anthranilamide compounds
CA2885115A1 (en) 2012-10-01 2014-04-10 Basf Se Pesticidal mixtures comprising jasmonic acid or a derivative thereof
EP2903442A1 (en) 2012-10-01 2015-08-12 Basf Se Pesticidally active mixtures comprising anthranilamide compounds
WO2014053403A1 (en) 2012-10-01 2014-04-10 Basf Se Method of controlling insecticide resistant insects
CR20190437A (en) 2012-10-02 2019-11-12 Bayer Cropscience Ag Heterocyclic compounds as pesticides
WO2014060381A1 (en) 2012-10-18 2014-04-24 Bayer Cropscience Ag Heterocyclic compounds as pesticides
CN102911131B (en) * 2012-10-24 2014-10-29 中化蓝天集团有限公司 Double-bond trifluoromethyl isoxazole compound, preparation method and application thereof
JP2016503395A (en) 2012-10-31 2016-02-04 バイエル・クロップサイエンス・アクチェンゲゼルシャフト Heterocyclic compounds as pest control agents
AU2013245478A1 (en) 2012-11-01 2014-05-15 Sumitomo Chemical Company, Limited Method for administering agent for controlling ectoparasite to dog
DE102012021647A1 (en) 2012-11-03 2014-05-08 Clariant International Ltd. Aqueous adjuvant compositions
UA117816C2 (en) 2012-11-06 2018-10-10 Байєр Кропсайєнс Акцієнгезелльшафт Herbicidal combinations for tolerant soybean cultures
AR093396A1 (en) * 2012-11-09 2015-06-03 Syngenta Participations Ag DERIVATIVES OF DIHYDROTIOPHENE AS INSECTICIDE COMPOUNDS
US9532946B2 (en) 2012-11-20 2017-01-03 Intervet Inc. Manufacturing of semi-plastic pharmaceutical dosage units
SI2922845T1 (en) 2012-11-20 2018-10-30 Merial, Inc. Anthelmintic compounds and compositions and method of using thereof
WO2014079935A1 (en) * 2012-11-21 2014-05-30 Syngenta Participations Ag Insecticidal compounds based on arylthioacetamide derivatives
CA2890162C (en) 2012-11-22 2023-03-21 Basf Corporation A pesticidal composition comprising bacillus pumilus
WO2014079770A1 (en) 2012-11-22 2014-05-30 Basf Se Pesticidal mixtures
WO2014079841A1 (en) 2012-11-22 2014-05-30 Basf Se Pesticidal mixtures
WO2014079804A1 (en) 2012-11-22 2014-05-30 Basf Se Pesticidal mixtures
AU2013349839B2 (en) 2012-11-22 2017-03-30 Basf Corporation Pesticidal mixtures
WO2014079774A1 (en) 2012-11-22 2014-05-30 Basf Se Pesticidal mixtures
WO2014079766A1 (en) 2012-11-22 2014-05-30 Basf Se Pesticidal mixtures
WO2014079772A1 (en) 2012-11-22 2014-05-30 Basf Se Pesticidal mixtures
BR112015011775A2 (en) 2012-11-22 2017-07-11 Basf Corp synergistic mixtures, kit for the preparation of a useful pesticide composition, pesticide composition, method for the protection of material and propagation material of plants.
WO2014079820A1 (en) 2012-11-22 2014-05-30 Basf Se Use of anthranilamide compounds for reducing insect-vectored viral infections
WO2014079728A1 (en) 2012-11-22 2014-05-30 Basf Se Pesticidal mixtures
WO2014079813A1 (en) 2012-11-23 2014-05-30 Basf Se Pesticidal mixtures
WO2014079752A1 (en) 2012-11-23 2014-05-30 Basf Se Pesticidal mixtures
CA3105365A1 (en) 2012-11-30 2014-06-05 Bayer Cropscience Ag Binary fungicidal mixtures
EA031510B1 (en) 2012-11-30 2019-01-31 Байер Кропсайенс Акциенгезельшафт Binary fungicidal mixture
WO2014086753A2 (en) 2012-12-03 2014-06-12 Bayer Cropscience Ag Composition comprising biological control agents
WO2014086758A2 (en) 2012-12-03 2014-06-12 Bayer Cropscience Ag Composition comprising a biological control agent and an insecticide
CN105451563A (en) 2012-12-03 2016-03-30 拜耳作物科学股份公司 Compositions comprising biological control agents
US20150289518A1 (en) 2012-12-03 2015-10-15 Bayer Cropscience Ag Composition comprising a biological control agent and an insecticide
EP2925142B1 (en) 2012-12-03 2018-01-31 Bayer CropScience AG Composition comprising a biological control agent and an insecticide
US20150305334A1 (en) 2012-12-05 2015-10-29 Bayer Cropscience Ag Use of substituted 1-(aryl ethynyl)-, 1-(heteroaryl ethynyl)-, 1-(heterocyclyl ethynyl)- and 1-(cycloalkenyl ethynyl)-cyclohexanols as active agents against abiotic plant stress
WO2014090765A1 (en) 2012-12-12 2014-06-19 Bayer Cropscience Ag Use of 1-[2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulfinyl)phenyl]-5-amino-3-trifluoromethyl)-1 h-1,2,4 tfia zole for controlling nematodes in nematode-resistant crops
WO2014090918A1 (en) 2012-12-13 2014-06-19 Novartis Ag Process for the enantiomeric enrichment of diaryloxazoline derivatives
CA2894023A1 (en) 2012-12-14 2014-06-19 Basf Se Malononitrile compounds for controlling animal pests
AR093996A1 (en) 2012-12-18 2015-07-01 Bayer Cropscience Ag BACTERICIDAL COMBINATIONS AND BINARY FUNGICIDES
KR20150100808A (en) 2012-12-21 2015-09-02 바스프 에스이 Cycloclavine and derivatives thereof for controlling invertebrate pests
CN105189489A (en) 2012-12-27 2015-12-23 巴斯夫欧洲公司 2-(pyridin-3-yl)-5-hetaryl-thiazole compounds carrying an imine or imine-derived substituent for combating invertebrate pests
EP2948439B1 (en) 2013-01-23 2020-06-03 Syngenta Participations AG Pyrazoline derivatives as insecticidal compounds
LT2953942T (en) 2013-02-06 2018-02-12 Bayer Cropscience Aktiengesellschaft Halogen-substituted pyrazole derivatives as pesticides
CA2899303A1 (en) 2013-02-11 2014-08-14 Bayer Cropscience Lp Compositions comprising gougerotin and a biological control agent
EP2953468A1 (en) 2013-02-11 2015-12-16 Bayer Cropscience LP Compositions comprising a streptomyces-based biological control agent and an insecticide
WO2014128136A1 (en) 2013-02-20 2014-08-28 Basf Se Anthranilamide compounds and their use as pesticides
WO2014131837A1 (en) 2013-02-28 2014-09-04 Syngenta Participations Ag Isoxaline derivatives for use in cotton plants
US9598389B2 (en) * 2013-03-06 2017-03-21 Syngenta Participations Ag Dihydrobenzofuran derivatives as insecticidal compounds
CN105208865A (en) 2013-03-12 2015-12-30 拜耳作物科学股份公司 Use of dithiine-tetracarboximides for controlling bacterial harmful organisms in useful plants
EP2986121A1 (en) 2013-04-19 2016-02-24 Bayer CropScience Aktiengesellschaft Active compound combinations having insecticidal properties
BR112015026357A2 (en) 2013-04-19 2017-07-25 Basf Se compost, agricultural or veterinary composition, methods for the control or control of pests, the protection of plants, the protection of propagating material and the treatment of animals and the use of a compost
BR112015025907A2 (en) 2013-04-19 2017-07-25 Bayer Cropscience Ag binary insecticide or pesticide mixture
CN104163791B (en) * 2013-05-20 2017-05-03 湖南化工研究院 N-pyridine (hetero) aryl amide compound and preparation method and application thereof
ES2712211T3 (en) 2013-06-20 2019-05-09 Bayer Cropscience Ag Derivatives of arylsulfide and arylsulfoxide acaricides and insecticides
ES2761571T3 (en) 2013-06-20 2020-05-20 Bayer Cropscience Ag Arylsulfide and arylsulfoxide derivatives as acaricides and insecticides
WO2014202751A1 (en) 2013-06-21 2014-12-24 Basf Se Methods for controlling pests in soybean
EP3013820A1 (en) * 2013-06-24 2016-05-04 Basf Se Bicyclyl-substituted isothiazoline compounds
EP3013819B1 (en) * 2013-06-24 2018-08-15 Merial, Inc. Isothiazoline compounds for combating invertebrate pests
JP2015028006A (en) 2013-06-27 2015-02-12 日産化学工業株式会社 Crystalline polymorph of isoxazoline compound and method for producing the same
JP6423873B2 (en) 2013-07-08 2018-11-14 バイエル・クロップサイエンス・アクチェンゲゼルシャフト 6-membered C-N-linked aryl sulfide derivatives and aryl sulfoxide derivatives as pest control agents
CN105531265B (en) 2013-07-15 2018-07-20 巴斯夫欧洲公司 Pesticidal compound
JP6404357B2 (en) 2013-09-19 2018-10-10 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ N-Acylimino Heterocyclic Compound
WO2015055554A1 (en) 2013-10-14 2015-04-23 Bayer Cropscience Ag Active substance for treating seed and soil
UY35772A (en) 2013-10-14 2015-05-29 Bayer Cropscience Ag NEW PESTICIDED COMPOUNDS
WO2015055497A1 (en) 2013-10-16 2015-04-23 Basf Se Substituted pesticidal pyrazole compounds
JP6644681B2 (en) 2013-10-18 2020-02-12 ビーエーエスエフ アグロケミカル プロダクツ ビー．ブイ． Use of pesticidally active carboxamide derivatives in soil and seed applications and methods of treatment
EP3060557A1 (en) 2013-10-23 2016-08-31 Bayer CropScience Aktiengesellschaft Substituted quinoxaline derivatives as pest control agent
US9371293B2 (en) 2013-10-25 2016-06-21 Sumitomo Chemical Company, Limited Isoxazoline compound composition
CA2929234C (en) * 2013-11-01 2022-01-11 Merial Limited Antiparisitic and pesticidal isoxazoline compounds
US9655884B2 (en) 2013-12-10 2017-05-23 Intervet Inc. Antiparasitic use of isoxazoline compounds
CN106029645A (en) 2013-12-18 2016-10-12 巴斯夫欧洲公司 N-substituted imino heterocyclic compounds
EP3083596A1 (en) 2013-12-18 2016-10-26 Basf Se Azole compounds carrying an imine-derived substituent
JP6506763B2 (en) 2013-12-20 2019-04-24 インターベット インターナショナル ベー． フェー． Use of isoxazoline derivatives for the treatment or prevention of arthropod infestation in poultry
CN105813651B (en) 2013-12-20 2021-11-23 英特维特国际股份有限公司 Isoxazoline compositions and their use in preventing or treating parasitic infestations of animals
CA2935646A1 (en) 2014-01-03 2015-07-09 Bayer Animal Health Gmbh Novel pyrazolyl-heteroarylamides as pesticides
WO2015104422A1 (en) 2014-01-13 2015-07-16 Basf Se Dihydrothiophene compounds for controlling invertebrate pests
WO2015107133A1 (en) 2014-01-20 2015-07-23 Bayer Cropscience Ag Quinoline derivatives as insecticides and acaricides
DE202014008418U1 (en) 2014-02-19 2014-11-14 Clariant International Ltd. Low foaming agrochemical compositions
DE202014008415U1 (en) 2014-02-19 2014-11-25 Clariant International Ltd. Aqueous adjuvant composition for increasing the effectiveness of electrolyte active substances
PE20161068A1 (en) * 2014-02-26 2016-10-21 Basf Se AZOLINE COMPOUNDS
WO2015150300A1 (en) 2014-04-02 2015-10-08 Bayer Cropscience Ag N-(1-(hetero)aryl-1h-pyrazol-4-yl)-(hetero)arylamide derivatives and use thereof as pesticides
WO2015160620A1 (en) 2014-04-16 2015-10-22 Bayer Cropscience Lp Compositions comprising ningnanmycin and an insecticide
WO2015160618A1 (en) 2014-04-16 2015-10-22 Bayer Cropscience Lp Compositions comprising ningnanmycin and a biological control agent
EP3131398B1 (en) 2014-04-17 2019-10-23 Boehringer Ingelheim Animal Health USA Inc. Use of malononitrile compounds for protecting animals from parasites
DE102014005771A1 (en) 2014-04-23 2015-10-29 Clariant International Ltd. Use of aqueous drift-reducing compositions
AU2015257746B2 (en) 2014-05-08 2018-11-22 Bayer Cropscience Aktiengesellschaft Pyrazolopyridine sulfonamides as nematicides
NZ726874A (en) 2014-05-19 2018-03-23 Merial Inc Anthelmintic compounds
CN106715424B (en) 2014-06-05 2020-07-14 拜耳作物科学股份公司 Bicyclic compounds as pesticides
BR122020023385B1 (en) 2014-06-19 2021-05-25 Merial, Inc parasiticidal compositions comprising indole derivatives, methods and uses thereof
CN106659160B (en) * 2014-06-30 2020-08-21 日产化学工业株式会社 Insecticidal or fungicidal composition and method for controlling plant diseases and pests
WO2016001119A1 (en) 2014-07-01 2016-01-07 Bayer Cropscience Aktiengesellschaft Insecticide and fungicide active ingredient combinations
WO2016008830A1 (en) 2014-07-15 2016-01-21 Bayer Cropscience Aktiengesellschaft Aryl-triazolyl pyridines as pest control agents
DE102014012022A1 (en) 2014-08-13 2016-02-18 Clariant International Ltd. Organic ammonium salts of anionic pesticides
EP3798214B1 (en) 2014-10-06 2022-09-14 Vertex Pharmaceuticals Incorporated Modulators of cystic fibrosis transmembrane conductance regulator
WO2016055096A1 (en) 2014-10-07 2016-04-14 Bayer Cropscience Ag Method for treating rice seed
US10864193B2 (en) 2014-10-31 2020-12-15 Boehringer Ingelheim Animal Health USA Inc. Parasiticidal compositions comprising fipronil at high concentrations
AR102942A1 (en) 2014-12-11 2017-04-05 Bayer Cropscience Ag DERIVATIVES OF ARILSULFIDE AND ARILSULPHOXIDE OF FIVE C-N-CONNECTED MEMBERS, AS PESTICIDES
DE102014018274A1 (en) 2014-12-12 2015-07-30 Clariant International Ltd. Sugar surfactants and their use in agrochemical compositions
EP3232780B1 (en) 2014-12-19 2021-08-04 Clariant International Ltd Aqueous electrolyte-containing adjuvant compositions, active ingredient-containing compositions and the use thereof
ES2733532T3 (en) * 2014-12-22 2019-11-29 Basf Se Azoline compounds substituted by a condensed carbocyclic ring system
BR112017013286A2 (en) 2014-12-22 2018-03-06 Intervet International B.V. isoxazoline compound, and use of an isoxazoline compound.
BR112017013579B1 (en) 2014-12-22 2022-01-04 Bayer Cropscience Lp. METHOD TO CONTROL CERATOCYSTIS PARADOXA IN A PLANT AND USE OF A COMPOSITION THAT COMPRISES A BIOLOGICAL CONTROL AGENT SELECTED FROM BACILLUS SUBTILIS, BACILLUS PUMILUS, METABOLITES PRODUCED FROM THEM AND COMBINATIONS THEREOF
MX2017008431A (en) 2014-12-22 2017-10-02 Basf Se Cyclic compounds substituted by a condensed ring system.
CR20170336A (en) 2014-12-22 2018-01-30 Basf Se AZOLINA COMPOUNDS REPLACED WITH A CONDENSED RING SYSTEM
EP3081085A1 (en) 2015-04-14 2016-10-19 Bayer CropScience AG Method for improving earliness in cotton
UY36548A (en) 2015-02-05 2016-06-01 Bayer Cropscience Ag BICYCLIC CONDENSED HETEROCYCLIC DERIVATIVES REPLACED BY 2- (HET) ARILO AS PESTICIDES
UY36547A (en) 2015-02-05 2016-06-01 Bayer Cropscience Ag BICYCLIC CONDENSED HETEROCYCLIC DERIVATIVES REPLACED BY 2- (HET) ARILO AS PESTICIDES
TWI702212B (en) 2015-02-09 2020-08-21 德商拜耳作物科學股份有限公司 Substituted 2-thioimidazolylcarboxamides as pesticides
UY36570A (en) 2015-02-26 2016-10-31 Merial Inc INJECTABLE FORMULATIONS OF PROLONGED ACTION THAT INCLUDE AN ISOXAZOLINE ACTIVE AGENT, METHODS AND USES OF THE SAME
WO2016142394A1 (en) 2015-03-10 2016-09-15 Bayer Animal Health Gmbh Pyrazolyl-derivatives as pest control agents
WO2016155831A1 (en) 2015-04-02 2016-10-06 Syngenta Participations Ag Isoxazoline-styrene derivatives as insecticidal compounds
EP3280716B1 (en) 2015-04-08 2020-02-12 Bayer CropScience AG Imidazo[1,2-a]pyridin-2-yl derivatives as pesticides and intermediates thereof
AU2016246598B2 (en) 2015-04-08 2020-07-23 Boehringer lngelheim Vetmedica GMBH Extended release injectable formulations comprising an isoxazoline active agent, methods and uses thereof
WO2016174049A1 (en) 2015-04-30 2016-11-03 Bayer Animal Health Gmbh Anti-parasitic combinations including halogen-substituted compounds
EP2910126A1 (en) 2015-05-05 2015-08-26 Bayer CropScience AG Active compound combinations having insecticidal properties
WO2016180802A1 (en) 2015-05-13 2016-11-17 Bayer Cropscience Aktiengesellschaft Insecticidal arylpyrrolidines, method for synthesizing same, and use thereof as agents for controlling animal pests
RU2707298C2 (en) 2015-05-20 2019-11-26 Мериал, Инк. Anthelminthic depsipeptide compounds
JP6933983B2 (en) 2015-06-23 2021-09-08 インターベット インターナショナル ベー． フェー． Vitamin E-containing isooxazoline solution for use with sanitized drinking water
KR20180025949A (en) 2015-07-06 2018-03-09 바이엘 크롭사이언스 악티엔게젤샤프트 Heterocyclic compounds as pesticides
CN105123298B (en) * 2015-07-08 2017-07-11 吉林省农业科学院 A kind of indoor bioassay method of non-selective identification Soybean Resistance eating-core bean worm
EP3331870B1 (en) 2015-08-07 2021-06-16 Bayer CropScience Aktiengesellschaft 2-(het)aryl-substituted condensed heterocycle derivatives as pesticides
AR106084A1 (en) * 2015-09-23 2017-12-13 Syngenta Participations Ag BENZAMIDS REPLACED WITH ISOXAZOLINE AS INSECTICIDES
AR106070A1 (en) * 2015-09-23 2017-12-06 Syngenta Participations Ag BENZAMIDS REPLACED WITH ISOXAZOLINE AS INSECTICIDES
DE102015219651A1 (en) 2015-10-09 2017-04-13 Clariant International Ltd. Compositions containing sugar amine and fatty acid
DE202015008045U1 (en) 2015-10-09 2015-12-09 Clariant International Ltd. Universal pigment dispersions based on N-alkylglucamines
WO2017132014A1 (en) * 2016-01-25 2017-08-03 Dow Agrosciences Llc Molecules having pesticidal utility, and intermediates, compositions, and processes, related thereto
CN109152363B (en) 2016-01-25 2021-10-15 美国陶氏益农公司 Molecules having pesticidal utility, and intermediates, compositions and methods related to these molecules
JP6923535B2 (en) * 2016-01-25 2021-08-18 コルテバ アグリサイエンス エルエルシー Molecules with pesticide utility and related intermediates, compositions, and processes
US20190059381A1 (en) 2016-02-19 2019-02-28 Basf Se Method for controlling pests of soybean, corn, and cotton plants
UY37137A (en) * 2016-02-24 2017-09-29 Merial Inc ANTIPARASITARY COMPOUNDS OF ISOXAZOLINE, INJECTABLE FORMULATIONS OF PROLONGED ACTION THAT INCLUDE THEM, METHODS AND USES OF THE SAME
EP3210468A1 (en) 2016-02-26 2017-08-30 Bayer CropScience Aktiengesellschaft Solvent-free formulations of low-melting point agents
CA3019380A1 (en) 2016-03-31 2017-10-05 Vertex Pharmaceuticals Incorporated Modulators of cystic fibrosis transmembrane conductance regulator
EP3440062B1 (en) 2016-04-06 2021-10-06 Boehringer Ingelheim Animal Health USA Inc. Process for the preparation of enantiomerically enriched isoxazoline compounds - crystalline toluene solvate of (s)-afoxolaner
WO2017186543A2 (en) 2016-04-24 2017-11-02 Bayer Cropscience Aktiengesellschaft Use of fluopyram and/or bacillus subtilis for controlling fusarium wilt in plants of the musaceae family
TWI679197B (en) * 2016-05-05 2019-12-11 瑞士商伊蘭科動物健康公司 Heteroaryl-1,2,4-triazole and heteroaryl-tetrazole compounds
DE202016003070U1 (en) 2016-05-09 2016-06-07 Clariant International Ltd. Stabilizers for silicate paints
EP3484877B1 (en) 2016-07-12 2020-07-01 Bayer CropScience Aktiengesellschaft Bicyclic compounds as pest controllers
US20190159451A1 (en) 2016-07-29 2019-05-30 Bayer Cropscience Aktiengesellschaft Active compound combinations and methods to protect the propagation material of plants
WO2018039508A1 (en) 2016-08-25 2018-03-01 Merial, Inc. Method for reducing unwanted effects in parasiticidal treatments
WO2018041665A1 (en) 2016-08-30 2018-03-08 Basf Se Method for controlling pests in modified plants
HUE056716T2 (en) 2016-09-30 2022-03-28 Vertex Pharma Modulator of cystic fibrosis transmembrane conductance regulator, pharmaceutical compositions, methods of treatment, and process for making the modulator
BR112019007483B1 (en) 2016-10-14 2023-10-17 Pi Industries Ltd 4-SUBSTITUTED PHENYLAMINE DERIVATIVES AND THEIR USE TO PROTECT CROPS BY FIGHTING UNWANTED PHYTOPATHOGENIC MICROORGANISMS
WO2018069841A1 (en) 2016-10-14 2018-04-19 Pi Industries Ltd 4-substituted phenylamine derivatives and their use to protect crops by fighting undesired phytopathogenic micoorganisms
EP3525590A1 (en) 2016-10-14 2019-08-21 Boehringer Ingelheim Animal Health USA Inc. Pesticidal and parasiticidal vinyl isoxazoline compounds
BR112019009977A2 (en) 2016-11-16 2019-08-27 Boehringer Ingelheim Animal Health Usa Inc anthelmintic depsipeptide compounds
EP3400801A1 (en) 2017-05-10 2018-11-14 Bayer CropScience Aktiengesellschaft Plant health effect of purpureocillium lilacinum
DK3551622T3 (en) 2016-12-09 2020-11-23 Vertex Pharma MODULATOR OF TRANSMEMBRANE CONDUCTANCE REGULATOR OF CYSTIC FIBROSE, PHARMACEUTICAL COMPOSITIONS, TREATMENT PROCEDURES AND METHOD OF MANUFACTURE OF THE MODULATOR
WO2018116072A1 (en) 2016-12-20 2018-06-28 Pi Industries Ltd. Heterocyclic compounds
WO2018116073A1 (en) 2016-12-21 2018-06-28 Pi Industries Ltd. 1, 2, 3-thiadiazole compounds and their use as crop protecting agent
TW201840542A (en) 2017-03-22 2018-11-16 瑞士商先正達合夥公司 Pesticidally active cyclopropyl methyl amide derivatives
WO2018172480A1 (en) * 2017-03-23 2018-09-27 Syngenta Participations Ag Insecticidal compounds
US11825838B2 (en) 2017-03-31 2023-11-28 Bayer Cropscience Aktiengesellschaft Tricyclic carboxamides for controlling arthropods
TWI780112B (en) 2017-03-31 2022-10-11 美商科迪華農業科技有限責任公司 Molecules having pesticidal utility, and intermediates, compositions, and processes, related thereto
WO2018177993A1 (en) 2017-03-31 2018-10-04 Bayer Cropscience Aktiengesellschaft Pyrazoles for controlling arthropods
AR111260A1 (en) 2017-03-31 2019-06-19 Intervet Int Bv PHARMACEUTICAL FORMULATION OF THE CROTONIL AMINO PIRIDINA SALT
TW201838965A (en) 2017-04-20 2018-11-01 印度商Ｐｉ工業公司 Novel phenylamine compounds
WO2018197466A1 (en) * 2017-04-26 2018-11-01 Basf Se Substituted succinimide derivatives as pesticides
CA3066084A1 (en) 2017-06-08 2018-12-13 Vertex Pharmaceuticals Incorporated Methods of treatment for cystic fibrosis
EP3638666B1 (en) * 2017-06-13 2021-07-21 Bayer Aktiengesellschaft Herbicidal 3-phenylisoxazoline-5-carboxamides of tetrahydro and dihydrofuran carboxylic acids amides
WO2019007888A1 (en) 2017-07-06 2019-01-10 Bayer Aktiengesellschaft Insecticidal active ingredient combinations
WO2019007891A1 (en) 2017-07-06 2019-01-10 Bayer Aktiengesellschaft Insecticidal active ingredient combinations
WO2019007887A1 (en) 2017-07-06 2019-01-10 Bayer Aktiengesellschaft Insecticide and fungicide active ingredient combinations
CA3069226A1 (en) 2017-07-17 2019-01-24 Vertex Pharmaceuticals Incorporated Methods of treatment for cystic fibrosis
AU2018309043B2 (en) 2017-08-02 2022-03-31 Vertex Pharmaceuticals Incorporated Processes for preparing pyrrolidine compounds
HUE061497T2 (en) * 2017-08-14 2023-07-28 Boehringer Ingelheim Animal Health Usa Inc Pesticidal and parasiticidal pyrazole-isoxazoline compounds
MY202302A (en) 2017-09-06 2024-04-23 Bayer Animal Health Gmbh Topically administrable formulation for the control and prevention of animal parasites
EP3473103A1 (en) 2017-10-17 2019-04-24 Bayer AG Aqueous suspension concentrates based on 2- [(2,4-dichlorophenyl) -methyl] -4,4 '-dimethyl-3-isoxazolidinone
TWI719349B (en) 2017-10-19 2021-02-21 美商維泰克斯製藥公司 Crystalline forms and compositions of cftr modulators
AU2018363682B2 (en) 2017-11-07 2023-11-23 Intervet International B.V. Injectable isoxazoline pharmaceutical compositions and their use against parasite infestation
CN111295375A (en) 2017-11-07 2020-06-16 英特维特国际股份有限公司 Method for producing large-size isoxazoline particles
KR102094916B1 (en) * 2017-12-04 2020-03-30 조명행 Insecticide composition for Dermanyssus gallinae, and the preparation method thereof
AU2018380426B2 (en) 2017-12-08 2023-05-18 Vertex Pharmaceuticals Incorporated Processes for making modulators of cystic fibrosis transmembrane conductance regulator
MX2020006055A (en) 2017-12-12 2020-08-20 Intervet Int Bv Implantable isoxazoline pharmaceutical compositions and uses thereof.
US10835517B2 (en) 2017-12-15 2020-11-17 Tarsus Pharmaceuticals, Inc. Methods for treating ocular demodex using isoxazoline parasiticide formulations
CA3085651A1 (en) 2017-12-20 2019-06-27 Pi Industries Ltd. Fluoralkenyl compounds, process for preparation and use thereof
AR113997A1 (en) 2017-12-21 2020-07-08 Intervet Int Bv ANTIPARASITIC COMPOSITIONS FOR CONTINUOUS DORSAL ANOINTING
CN108191784B (en) * 2018-01-12 2020-03-06 洛阳师范学院 5-difluoroethyl [4,5] dihydroisoxazole derivative and preparation method thereof
WO2019150311A1 (en) 2018-02-02 2019-08-08 Pi Industries Ltd. 1-3 dithiol compounds and their use for the protection of crops from phytopathogenic microorganisms
TWI810243B (en) 2018-02-05 2023-08-01 美商維泰克斯製藥公司 Pharmaceutical compositions for treating cystic fibrosis
US11583545B2 (en) 2018-02-08 2023-02-21 Boehringer Ingelheim Animal Health USA Inc. Parasiticidal compositions comprising eprinomectin and praziquantel, methods and uses thereof
WO2019200246A1 (en) 2018-04-13 2019-10-17 Alexander Russell Abela Modulators of cystic fibrosis transmembrane conductance regulator, pharmaceutical compositions, methods of treatment, and process for making the modulator
WO2020002189A1 (en) 2018-06-27 2020-01-02 Bayer Aktiengesellschaft Active substance combinations
WO2020002593A1 (en) 2018-06-29 2020-01-02 Intervet International B.V. Compound for use against helminthic infection
WO2020014068A1 (en) 2018-07-09 2020-01-16 Boehringer Ingelheim Animal Health USA Inc. Anthelminthic heterocyclic compounds
MX2021001044A (en) 2018-07-27 2021-04-12 Bayer Ag Controlled release formulations for agrochemicals.
BR112021001633A2 (en) 2018-07-31 2021-05-04 Bayer Aktiengesellschaft controlled release formulations with lignin for agrochemicals
WO2020035826A1 (en) 2018-08-17 2020-02-20 Pi Industries Ltd. 1,2-dithiolone compounds and use thereof
AU2019348400A1 (en) * 2018-09-26 2021-04-01 Syngenta Crop Protection Ag Pesticidally active cyclopropyl methyl amide derivatives
EP3856715A1 (en) * 2018-09-26 2021-08-04 Syngenta Participations Ag Insecticidal compounds
AU2019369659A1 (en) 2018-10-29 2021-04-29 Basf Se Process for preparation of optically enriched aldol compounds
AU2019376282A1 (en) 2018-11-06 2021-05-20 Basf Se Process for preparation of optically enriched isoxazolines
EP3883648A1 (en) 2018-11-20 2021-09-29 Boehringer Ingelheim Animal Health USA Inc. Indazolylcyanoethylamino compound, compositions of same, method of making, and methods of using thereof
KR20210100149A (en) 2018-12-04 2021-08-13 바스프 에스이 Process for the preparation of 5-bromo-1,3-dichloro-2-fluoro-benzene
AU2019400839A1 (en) 2018-12-21 2021-06-17 Intervet International B.V. Method for producing (5S)-4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4Hisoxazol-3-yl]-2-methyl-benzonic acid
AU2019408398A1 (en) 2018-12-21 2021-06-17 Intervet International B.V. Method for racemisation of (5R)-4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2-methyl-benzoic acid
AR115291A1 (en) 2018-12-21 2020-12-16 Intervet Int Bv METHOD TO PRODUCE (5S) -4- [5- (3,5-DICHLOROPHENYL) -5- (TRIFLUOROMETHYL) -4H-ISOXAZOL-3-IL] -2-METHYL-BENZOIC ACID
NZ776819A (en) 2019-01-16 2023-04-28 Boehringer Ingelheim Animal Health Usa Inc Topical compositions comprising a neonicotinoid and a macrocyclic lactone, methods and uses thereof
EP3696177A1 (en) 2019-02-12 2020-08-19 Basf Se Heterocyclic compounds for the control of invertebrate pests
WO2020180635A1 (en) 2019-03-01 2020-09-10 Boehringer Ingelheim Animal Health USA Inc. Injectable clorsulon compositions, methods and uses thereof
CN109879826B (en) * 2019-03-18 2021-04-13 丽珠集团新北江制药股份有限公司 Preparation method of isoxazoline insecticide
CA3133100A1 (en) 2019-03-19 2020-09-24 Boehringer Ingelheim Animal Health USA Inc. Anthelmintic aza-benzothiophene and aza-benzofuran compounds
BR112021021649A2 (en) 2019-05-03 2021-12-21 Intervet Int Bv Injectable pharmaceutical compositions and uses thereof
CN110199999A (en) * 2019-06-19 2019-09-06 江西正邦作物保护有限公司 A kind of composition pesticide containing fluorine oxazole amide and Tolfenpyrad
JP7485667B2 (en) * 2019-06-21 2024-05-16 日本農薬株式会社 Oxadiazole compounds or salts thereof, agricultural and horticultural fungicides containing said compounds, and methods of using the same
CN112174904B (en) * 2019-07-01 2023-08-18 沈阳化工大学 Isoxazoline compound and application thereof
US20220323421A1 (en) 2019-07-22 2022-10-13 Intervet Inc. Soft Chewable Veterinary Dosage Form
BR112022004347A8 (en) 2019-09-11 2022-10-18 Bayer Ag HIGHLY EFFECTIVE FORMULATIONS BASED ON 2-[(2,4-DICHLOROPHENYL)-METHYL]-4,4'-DIMETHYL-3-ISOXAZOLIDINONE AND PRE-EMERGENCY HERBICIDES
WO2021122515A1 (en) 2019-12-16 2021-06-24 Intervet International B.V. Parasite control in ruminants
AU2020409532A1 (en) 2019-12-16 2022-05-12 Intervet International B.V. Composition for lice control
WO2021122521A1 (en) 2019-12-16 2021-06-24 Intervet International B.V. Composition for lice control in poultry
WO2021122356A1 (en) 2019-12-17 2021-06-24 Krka, D.D., Novo Mesto Process for preparing fluralaner
MX2022007455A (en) * 2019-12-18 2022-08-15 Elanco Tiergesundheit Ag Isoxazoline derivatives as pesticides.
TW202136238A (en) * 2020-01-06 2021-10-01 大陸商廣東東陽光藥業有限公司 ROR[gamma]T inhibitor, preparation method therefor and use thereof
CN113354551B (en) * 2020-03-04 2024-08-23 东莞市东阳光动物保健药品有限公司 Preparation method of amide compound
CN113461653B (en) * 2020-03-30 2022-09-02 洛阳惠中兽药有限公司 Method for preparing fraxidin intermediate, and preparation intermediate and application thereof
JP2023077429A (en) * 2020-04-22 2023-06-06 日本曹達株式会社 Benzamide compounds and pest control agent
CN115666514A (en) 2020-05-20 2023-01-31 英特维特国际股份有限公司 Injectable pharmaceutical composition and use thereof
WO2021242481A1 (en) 2020-05-28 2021-12-02 Boehringer Ingelheim Animal Health USA Inc. Bi-modal release intra-ruminal capsule device and methods of use thereof
KR20230028268A (en) 2020-05-29 2023-02-28 뵈링거 잉겔하임 애니멀 헬스 유에스에이 인코포레이티드 Anthelmintic Heterocyclic Compounds
CN113773269A (en) * 2020-06-09 2021-12-10 海门慧聚药业有限公司 Crystal form of frairana and preparation method thereof
CN111689919A (en) * 2020-07-22 2020-09-22 天津市中升挑战生物科技有限公司 Synthetic method of isoxazoline anthelmintic
CN111909143B (en) 2020-07-30 2021-10-29 山东省联合农药工业有限公司 Isoxazoline substituted benzamide derivative and preparation method and application thereof
CN111955469A (en) * 2020-08-28 2020-11-20 武汉麦世吉科技有限公司 Pesticide for cucumbers and cucumber pest control method
US12108762B2 (en) * 2020-09-08 2024-10-08 Santanu Maitra Methods of controlling crop pests using aromatic amide insect repellents, methods of making aromatic amide insect repellents, and novel aromatic amide insect repellents
TW202237593A (en) * 2020-12-11 2022-10-01 印度商皮埃企業有限公司 Isoxazoline compounds and their use as pest control agents
CA3205997A1 (en) 2020-12-21 2022-06-30 University Of Georgia Research Foundation Inc. Parasiticidal collar comprising isoxazoline compounds
CN114736168B (en) * 2021-01-07 2024-08-09 沈阳中化农药化工研发有限公司 Isoxazoline derivative containing tranexamic acid fragment and preparation and application thereof
US20240116854A1 (en) 2021-01-27 2024-04-11 Intervet Inc. Cyclopropylamide compounds against parasites in fish
WO2022162016A1 (en) 2021-01-27 2022-08-04 Intervet International B.V. Cyclopropylamide compounds against parasites in fish
KR20230137956A (en) 2021-01-28 2023-10-05 스페셜티 오퍼레이션스 프랑스 Rice seed treatment method that improves pesticide, micronutrient and colorant retention
CN112939728A (en) * 2021-02-03 2021-06-11 石家庄手性化学有限公司 Preparation method of frainer intermediate 1, 3-dichloro-alpha- (trifluoromethyl) styrene
KR20230145066A (en) 2021-02-11 2023-10-17 바스프 에스이 Substituted Isoxazoline Derivatives
EP4043444A1 (en) 2021-02-11 2022-08-17 Basf Se Substituted isoxazoline derivatives
CN115246795B (en) * 2021-04-26 2024-01-02 瑞普（天津）生物药业有限公司 Isoxazoline compound containing ether structure at 4-phenyl para-position, preparation method thereof and application thereof as insecticidal and bactericidal agent
US20240260577A1 (en) 2021-05-14 2024-08-08 Syngenta Crop Protection Ag Insect, acarina and nematode pest control
IL309139A (en) 2021-06-11 2024-02-01 Intervet Int Bv Tick control methods
JP2024523313A (en) 2021-06-16 2024-06-28 エランコ・ティアゲゾンタイト・アーゲー Isoxazoline insecticide
AU2022293478A1 (en) * 2021-06-16 2023-11-30 ELANCO US, Inc. Crystalline forms of isoxazoline compound
EP4355746A1 (en) * 2021-06-16 2024-04-24 Elanco Tiergesundheit AG (thi)oxazoline pesticides
WO2022269042A1 (en) 2021-06-25 2022-12-29 Intervet International B.V. Palatable veterinary compositions
CN113563322B (en) * 2021-07-26 2023-07-07 海利尔药业集团股份有限公司 Substituted benzamide isoxazoline derivative or salt acceptable as pesticide, composition and application thereof
CN114907236B (en) * 2021-08-26 2024-02-09 四川青木制药有限公司 Aldoxime compound and preparation method and application thereof
CN113582987B (en) * 2021-09-02 2023-06-30 海利尔药业集团股份有限公司 Substituted benzamide isoxazoline derivative or salt acceptable as pesticide, composition and application thereof
WO2023078915A1 (en) 2021-11-03 2023-05-11 Bayer Aktiengesellschaft Bis(hetero)aryl thioether (thio)amides as fungicidal compounds
WO2023092050A1 (en) 2021-11-20 2023-05-25 Bayer Cropscience Lp Beneficial combinations with recombinant bacillus cells expressing a serine protease
CN113896690B (en) * 2021-11-22 2023-04-21 常州齐晖药业有限公司 Preparation method of isoxazoline anthelmintic fluorine Lei Lana
EP4441049A1 (en) 2021-11-30 2024-10-09 Bayer Aktiengesellschaft Bis(hetero)aryl thioether oxadiazines as fungicidal compounds
CN118525195A (en) 2021-12-15 2024-08-20 拜耳公司 Spectroscopic protocol for non-destructive quantification of one or more chemicals in a substrate comprising a coating and a bulk material in a sample, such as a coated seed, using multivariate data analysis
KR102660238B1 (en) * 2021-12-20 2024-04-25 주식회사경농 Dihydroisoxazole derivative compound and pesticide composition comprising same
WO2023118434A1 (en) * 2021-12-22 2023-06-29 Globachem Nv Pesticidally active amide compounds
CN114539180A (en) * 2021-12-24 2022-05-27 贵州大学 Isoxazoline-containing bisamide compound and preparation method and application thereof
CN114394963B (en) * 2022-01-12 2023-05-23 西北农林科技大学 Isoxazoline compound, preparation method and application
CN114380762A (en) * 2022-01-23 2022-04-22 贵州大学 Isoxazoline hydrazide derivative and preparation method and application thereof
WO2023156938A1 (en) 2022-02-17 2023-08-24 Boehringer Ingelheim Vetmedica Gmbh Method and system for providing a fluid product mailer
CN114605324A (en) * 2022-03-28 2022-06-10 山东省联合农药工业有限公司 Isoxazoline substituted benzamide derivative and preparation method and application thereof
WO2023203038A1 (en) 2022-04-19 2023-10-26 Syngenta Crop Protection Ag Insect, acarina and nematode pest control
CN114853748A (en) * 2022-05-06 2022-08-05 武汉工程大学 Trifluoromethyl-containing isoxazoline derivative, and preparation method and application thereof
CN117126116A (en) * 2022-05-20 2023-11-28 天津瑞普生物技术股份有限公司 Derivative of isoxazoline compound and application thereof
KR20240002746A (en) * 2022-06-30 2024-01-08 주식회사경농 Isoxazoline derivative compound and pesticide composition comprising the same
CN117402154A (en) * 2022-07-13 2024-01-16 安徽圣丰生化有限公司 Pyrazole structure-containing compound and application and pesticide
CN115057799B (en) * 2022-07-21 2023-11-24 湖南海利常德农药化工有限公司 Method for preventing color change of fenobucarb technical
WO2024047241A1 (en) 2022-09-02 2024-03-07 Intervet International B.V. Treatment of fasciolosis
WO2024061178A1 (en) * 2022-09-21 2024-03-28 青岛康乔药业集团有限公司 Compound containing five-membered heterocycle, preparation method therefor, and application thereof
WO2024066128A1 (en) * 2022-10-01 2024-04-04 青岛清原化合物有限公司 Isoxazoline substituted benzamide compound and use thereof
DK202470076A1 (en) 2023-03-13 2024-10-10 Zoetis Services Llc Degradation of isoxazolines in ozonated sea water
WO2024201231A1 (en) * 2023-03-24 2024-10-03 Hikal Limited A process for the preparation of isoxazoline-substituted amide compounds and its intermediates thereof

Family Cites Families (94)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2909509A (en) 1956-08-16 1959-10-20 Minnesota Mining & Mfg Fluorine-containing polymers and preparation thereof
US3391203A (en) * 1963-10-10 1968-07-02 Dow Chemical Co Alpha-(2, 2-dichloroethyl) styrene
GB1314812A (en) 1969-05-20 1973-04-26 Ici Ltd Trifluoromethyl heterocyclic derivatives and compositions containing them
US3968207A (en) 1973-12-10 1976-07-06 American Cyanamid Company Method of controlling fleas and ticks on cats and dogs
US4018801A (en) * 1973-12-12 1977-04-19 The Dow Chemical Company Substituted oxirane compounds
US3879532A (en) 1974-01-18 1975-04-22 Shell Oil Co Control by isoxazoles of endoparasitic nematodes
ES437117A1 (en) * 1974-05-03 1977-04-16 Dow Chemical Co 2-chloroalkyl-2-3,5-disubstituted phenyl-oxiranes
US4129568A (en) 1977-05-12 1978-12-12 Monsanto Company 2-[3-Aryl-2-isoxazolin-5-yl]benzoates
JPS6026119B2 (en) 1977-06-09 1985-06-21 三共株式会社 Organophosphate esters and insecticides and acaricides containing them
CA1119178A (en) 1977-06-09 1982-03-02 Keigo Matsumoto Mono- and di- thiophosphate esters containing an isoxazolinone ring
EP0074069B1 (en) 1981-09-03 1986-01-08 Daikin Kogyo Co., Ltd. Process for preparing chlorotrifluoromethylbenzene
JPS58194869A (en) 1982-05-10 1983-11-12 Sankyo Co Ltd Isoxazolinone derivative and insecticide and acaricide
DE3335477A1 (en) * 1983-09-30 1985-04-18 Bayer Ag, 5090 Leverkusen 2-ARYL-2-HALOGENALKYL-OXIRANE
US4629492A (en) * 1984-10-26 1986-12-16 The Dow Chemical Company Substituted oxirane compounds
GB8523126D0 (en) 1985-09-19 1985-10-23 Ici Plc Aryl pyridones
US5154749A (en) * 1985-11-04 1992-10-13 Dowelanco Herbicidal latex dispersion for controlled delivery and release of herbicides and their preparation
CS265658B1 (en) * 1986-01-31 1989-11-14 Paryzkova Jana Method of parallel quantitative determination of by-products in tetrabromodiade
US5075320A (en) 1989-01-04 1991-12-24 Rehmert Chalmer V Jr Method and composition for treating parasitic infestation of animals
DE4013723A1 (en) 1990-04-28 1991-10-31 Basf Ag 5- (1,2,4-TRIAZOL-1-YLMETHYL) -ISOXAZOLINE
GB9205007D0 (en) 1992-03-07 1992-04-22 Pfizer Ltd Antiparasitic agents
JP3313152B2 (en) * 1992-09-16 2002-08-12 スズキ株式会社 Motorcycle engine start and steering lock device
WO1995019773A1 (en) 1992-10-07 1995-07-27 Merck & Co., Inc. Carbostyril oxytocin receptor antagonists
US5569655A (en) 1993-09-14 1996-10-29 Sterling Winthrop Inc. Substituted heterocyclylisoquinolinium salts and compositions and method of use thereof
HUT74690A (en) 1993-11-24 1997-01-28 Du Pont Merck Pharma Novel isoxazoline and isoxazole fibrinogen receptor antagonists process for producing them and pharmaceutical compositions containing them
US5849736A (en) 1993-11-24 1998-12-15 The Dupont Merck Pharmaceutical Company Isoxazoline and isoxazole fibrinogen receptor antagonists
DK0730588T3 (en) * 1993-11-26 1997-12-08 Pfizer Isoxazoline compounds as anti-inflammatory agents
US5869511A (en) 1994-03-09 1999-02-09 Pfizer Inc. Isoxazoline compounds as inhibitors of TNF release
DE4408084A1 (en) * 1994-03-10 1995-09-14 Hoechst Ag 3,5-disubstituted and 3,4,5-trisubstituted 2-isoxazolines and isoxazoles, processes for their preparation and their use as medicaments
JPH07324045A (en) 1994-05-27 1995-12-12 Seimi Chem Co Ltd Tolan derivative compound and liquid crystal composition containing the same
TR199701667T2 (en) 1995-06-21 1999-10-21 Shionogi & Co.,Ltd. Double-cycle amino derivatives and PGD2 antagonist containing these derivatives.
JP2001502655A (en) 1995-12-21 2001-02-27 デュポン ファーマシューティカルズ カンパニー Isoxazoline, isothiazoline and pyrazoline which are factor Xa inhibitors
CN1076351C (en) 1996-04-26 2001-12-19 日本曹达株式会社 Heterocyclic substituted benzene derivatives and herbicides
WO1997048395A1 (en) 1996-06-19 1997-12-24 Du Pont Pharmaceuticals Company Iontophoretic delivery of integrin inhibitors
FR2750861B1 (en) 1996-07-11 1998-12-24 Rhone Merieux PROCESSES FOR REMOVING PARASITES, ESPECIALLY VERTEBRATE ECTOPARASITES, ESPECIALLY MAMMALS AND COMPOSITIONS FOR CARRYING OUT THIS PROCESS
DE19713626A1 (en) 1997-04-02 1998-10-08 Bayer Ag New thiodepsipeptides to control endoparasites and a simple process for their preparation
US5932766A (en) 1997-05-30 1999-08-03 Abbott Laboratories Process for the preparation of substituted keto-enamines
JP2002507968A (en) 1997-06-19 2002-03-12 デュポン ファーマシューティカルズ カンパニー Factor Xa inhibitor having a neutral P1 specific group
AU9198698A (en) 1997-09-15 1999-04-05 Warner-Lambert Company Process for the preparation of substituted 5,6-dihydro-2h-pyran-2-ones
CO5031296A1 (en) 1997-11-04 2001-04-27 Novartis Ag DERIVATIVES OF AZOLINA, COMPOUNDS THAT CONTAIN IT AND METHOD FOR THE PREPARATION AND APPLICATION OF SUCH COMPOUND
RU2129430C1 (en) 1998-03-17 1999-04-27 Общество С Ограниченной Ответственностью "Вик - Здоровье Животных" Preparation "santomectin" for ecto- and endoparasites control in animals
ATE295167T1 (en) 1998-03-19 2005-05-15 Merck & Co Inc SULFUR PENTAFLUOROPHENYLPYRAZOLES FOR CONTROLLING ECTOPARASITE INFECTION
US6136838A (en) 1998-03-19 2000-10-24 Merck & Co., Inc. Sulfurpentafluorophenylpyrazoles for controlling ectoparasitic infestations
US6140350A (en) 1998-06-08 2000-10-31 Sumitomo Chemical Company, Limited Method for controlling ectoparasites
CN1161018C (en) 1998-06-18 2004-08-11 诺瓦提斯公司 Composition for keeping away vermin
ATE241908T1 (en) 1998-10-09 2003-06-15 Novartis Pharma Gmbh ORAL COMBINATION OF LUFENURON AND NITENPYRAM AGAINST FLES
EG22187A (en) 1999-04-15 2002-10-31 Aventis Cropscience Sa New composition
JP3722700B2 (en) 1999-05-04 2005-11-30 シェーリング コーポレイション Piperazine derivatives useful as CCR5 antagonists
GB2351081A (en) 1999-06-18 2000-12-20 Lilly Forschung Gmbh Pharmaceutically active imidazoline compounds and analogues thereof
AU775488B2 (en) 1999-08-12 2004-08-05 Elanco Us Inc. Oral treatment of companion animals with ectoparasiticidal spinosyns
AU2160201A (en) 1999-11-19 2001-05-30 Novartis Ag Organic compounds and their use in the control of ectoparasites
MY129771A (en) 1999-12-02 2007-04-30 Merial Ltd Control of arthropods in animals
GB9928568D0 (en) 1999-12-03 2000-02-02 Zeneca Ltd Chemical compounds
HUP0300850A2 (en) 2000-03-17 2003-07-28 Bristol-Myers Squibb Pharma Company Cyclic betha-amino acid derivatives as inhibitors of matrix metalloproteases and tnf-alpha and pharmaceutical compositions containing them and their use
US6579880B2 (en) * 2000-06-06 2003-06-17 Ortho-Mcneil Pharmaceutical, Inc. Isoxazoles and oxadiazoles as anti-inflammatory inhibitors of IL-8
AU2001268712A1 (en) 2000-06-23 2002-01-08 Bristol-Myers Squibb Company 1 - (heteroaryl-phenyl) - condensed pyrazol derivatives as factor Xa inhibitors
AU2001268711A1 (en) 2000-06-23 2002-01-08 Bristol-Myers Squibb Pharma Company Heteroaryl-phenyl substituted factor xa inhibitors
AU2001273040A1 (en) 2000-06-27 2002-01-08 Du Pont Pharmaceuticals Company Factor xa inhibitors
DE10042736A1 (en) 2000-08-31 2002-03-14 Bayer Ag Active ingredient combinations with insecticidal and acaricidal properties
DE10114597A1 (en) 2001-03-23 2002-10-02 Bayer Cropscience Gmbh Arylisoxazoline derivatives, process for their preparation and their use as pesticides
WO2002100332A2 (en) 2001-06-08 2002-12-19 Cytokine Pharmasciences, Inc. Isoxazoline compounds having mif antagonist activity
BR0313943A (en) * 2002-08-26 2005-08-02 Nissan Chemical Ind Ltd Substituted benzanilide compound and harmful organism control agent
US20040069235A1 (en) 2002-09-27 2004-04-15 Rasa Cordelia G. Flea feeding apparatus
DE10320782A1 (en) 2003-05-09 2004-11-25 Bayer Cropscience Ag Substituted oxyarenes
ATE411799T1 (en) 2003-11-04 2008-11-15 Intervet Int Bv ECTOPARASITIC FORMULATIONS OF SPINOSYNS AND AZOLE PESTICIDES
GB0402677D0 (en) 2003-11-06 2004-03-10 Novartis Ag Organic compounds
JP2005272452A (en) 2004-02-23 2005-10-06 Nissan Chem Ind Ltd Substituted benzanilide compound and pesticide
CN1930136B (en) 2004-03-05 2012-02-08 日产化学工业株式会社 Isoxazoline-substituted benzamide compound and noxious organism control agent
MXPA06010793A (en) * 2004-03-26 2006-12-19 Cytokine Pharmasciences Inc Compouns, compositions, processes of making, and methods of use related to inhibiting macrophage migration inhibitory factor.
DE602005023881D1 (en) 2004-07-28 2010-11-11 Intervet Int Bv VETERINARY MEDICINE COMPOSITION WITH AN ARYLPYRAZOLE AND A NITROENAMINE WITH INCREASED ANTIPARASITIC ACTIVITY
EP1868616A2 (en) 2005-03-29 2007-12-26 The University of Maryland, Baltimore Inhibitors for extracellular signal-regulated kinase docking domains and uses therefor
JP5051340B2 (en) 2005-06-06 2012-10-17 日産化学工業株式会社 Substituted isoxazoline compounds and pest control agents
MY146795A (en) 2005-06-09 2012-09-28 Novartis Ag Process for the synthesis of organic compounds
ES2443690T3 (en) 2005-09-02 2014-02-20 Nissan Chemical Industries, Ltd. Isoxazoline-substituted benzamide compound and harmful agent controlling agent
JP2007106756A (en) 2005-09-14 2007-04-26 Nissan Chem Ind Ltd Substituted isoxazoline compound and pesticide
EP1965645A2 (en) 2005-12-14 2008-09-10 E.I. Du Pont De Nemours And Company Isoxazolines for controlling invertebrate pests
TW200803740A (en) 2005-12-16 2008-01-16 Du Pont 5-aryl isoxazolines for controlling invertebrate pests
US7700808B2 (en) 2005-12-26 2010-04-20 Nissan Chemical Industries, Ltd. 1-3-bis(substituted phenyl)-3-hydroxypropan-1-one or 2-propen-1-one compound, and salt thereof
TWI412322B (en) 2005-12-30 2013-10-21 Du Pont Isoxazolines for controlling invertebrate pests
DE602007006288D1 (en) 2006-03-10 2010-06-17 Nissan Chemical Ind Ltd SUBSTITUTED ISOXAZOLIN COMPOUND AND PESTICIDES
AU2007240954A1 (en) 2006-04-20 2007-11-01 E. I. Du Pont De Nemours And Company Pyrazolines for controlling invertebrate pests
JPWO2007125984A1 (en) 2006-04-28 2009-09-10 日本農薬株式会社 Isoxazoline derivatives, pest control agents and methods of use
JP2008044880A (en) 2006-08-15 2008-02-28 Bayer Cropscience Ag Insecticidal isooxazolines
WO2008108448A1 (en) 2007-03-07 2008-09-12 Nissan Chemical Industries, Ltd. Isoxazoline-substituted benzamide compound and pest control agent
NZ580241A (en) 2007-04-10 2011-02-25 Bayer Cropscience Ag Insecticidal aryl isoxazoline derivatives
AU2008261793A1 (en) 2007-06-13 2008-12-18 E. I. Du Pont De Nemours And Company Isoxazoline insecticides
TWI430995B (en) 2007-06-26 2014-03-21 Du Pont Naphthalene isoxazoline invertebrate pest control agents
US8952175B2 (en) 2007-06-27 2015-02-10 Nissan Chemical Industries, Ltd. Method for production of 3-hydroxypropan-1-one compound, method for production of 2-propen-1-one compound and method for production of isoxazoline compound
MX361762B (en) 2007-06-27 2018-12-17 Du Pont Animal pest control method.
TWI649303B (en) 2007-08-17 2019-02-01 杜邦股份有限公司 Compound and method for preparing 4-acetyl-n-[2-oxo-2-[(2,2,2-trifluoroethyl)amino]ethyl]-1-naphthalenecarboxamide
TWI556741B (en) 2007-08-17 2016-11-11 英特威特國際股份有限公司 Isoxazoline compositions and their use as antiparasitics
US8318757B2 (en) 2007-09-10 2012-11-27 Nissan Chemical Industries, Ltd. Substituted isoxazoline compound and pest control agent
US8367584B2 (en) 2007-10-03 2013-02-05 E.I. Du Pont De Nemours And Company Naphthalene isoxazoline compounds for control of invertebrate pests
TWI583664B (en) 2008-04-09 2017-05-21 杜邦股份有限公司 Carbonyl compound and method for preparing thereof
AU2009270255B2 (en) 2008-07-09 2013-12-12 Nissan Chemical Corporation Process for production of isoxazoline-substituted benzoic acid amide compound

Cited By (3)

* Cited by examiner, † Cited by third party
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