JPH01197471A - Pyrazole oxime derivative and insecticide, acaricide and germicide - Google Patents
Pyrazole oxime derivative and insecticide, acaricide and germicideInfo
- Publication number
- JPH01197471A JPH01197471A JP2245488A JP2245488A JPH01197471A JP H01197471 A JPH01197471 A JP H01197471A JP 2245488 A JP2245488 A JP 2245488A JP 2245488 A JP2245488 A JP 2245488A JP H01197471 A JPH01197471 A JP H01197471A
- Authority
- JP
- Japan
- Prior art keywords
- group
- carbon atoms
- oii
- chz
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- -1 Pyrazole oxime Chemical class 0.000 title claims abstract description 13
- 239000002917 insecticide Substances 0.000 title claims abstract description 13
- 230000000895 acaricidal effect Effects 0.000 title claims abstract description 11
- 239000000642 acaricide Substances 0.000 title claims abstract description 9
- 230000002070 germicidal effect Effects 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 61
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 11
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 5
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 3
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 35
- 239000004480 active ingredient Substances 0.000 claims description 20
- 239000000126 substance Substances 0.000 claims description 18
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000001188 haloalkyl group Chemical group 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 4
- 239000003899 bactericide agent Substances 0.000 claims description 3
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 2
- 230000000844 anti-bacterial effect Effects 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 abstract description 5
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 3
- 238000002360 preparation method Methods 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 150000002367 halogens Chemical class 0.000 abstract 3
- 239000000463 material Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 26
- 239000003795 chemical substances by application Substances 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 239000000839 emulsion Substances 0.000 description 12
- 241000607479 Yersinia pestis Species 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000000843 powder Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000009969 flowable effect Effects 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 241000238876 Acari Species 0.000 description 5
- 240000008067 Cucumis sativus Species 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 238000011081 inoculation Methods 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- 239000000454 talc Substances 0.000 description 5
- 229910052623 talc Inorganic materials 0.000 description 5
- 241000239290 Araneae Species 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 239000000417 fungicide Substances 0.000 description 4
- 230000000749 insecticidal effect Effects 0.000 description 4
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 4
- 229910052622 kaolinite Inorganic materials 0.000 description 4
- 230000003071 parasitic effect Effects 0.000 description 4
- 238000003892 spreading Methods 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 235000009849 Cucumis sativus Nutrition 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 241000238631 Hexapoda Species 0.000 description 3
- 241000488589 Tetranychus kanzawai Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 241000209140 Triticum Species 0.000 description 3
- 235000021307 Triticum Nutrition 0.000 description 3
- 239000003945 anionic surfactant Substances 0.000 description 3
- 239000000440 bentonite Substances 0.000 description 3
- 229910000278 bentonite Inorganic materials 0.000 description 3
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 3
- 229910000019 calcium carbonate Inorganic materials 0.000 description 3
- RYAGRZNBULDMBW-UHFFFAOYSA-L calcium;3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Ca+2].COC1=CC=CC(CC(CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O RYAGRZNBULDMBW-UHFFFAOYSA-L 0.000 description 3
- 230000000887 hydrating effect Effects 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000255749 Coccinellidae Species 0.000 description 2
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241000336797 Eoeurysa flavocapitata Species 0.000 description 2
- 241000221785 Erysiphales Species 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 230000000855 fungicidal effect Effects 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000005645 nematicide Substances 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- 239000000230 xanthan gum Substances 0.000 description 2
- 229920001285 xanthan gum Polymers 0.000 description 2
- 229940082509 xanthan gum Drugs 0.000 description 2
- 235000010493 xanthan gum Nutrition 0.000 description 2
- ZGYIXVSQHOKQRZ-COIATFDQSA-N (e)-n-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]-3-cyano-7-[(3s)-oxolan-3-yl]oxyquinolin-6-yl]-4-(dimethylamino)but-2-enamide Chemical compound N#CC1=CN=C2C=C(O[C@@H]3COCC3)C(NC(=O)/C=C/CN(C)C)=CC2=C1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 ZGYIXVSQHOKQRZ-COIATFDQSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 241000238678 Boophilus Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 1
- 101100027969 Caenorhabditis elegans old-1 gene Proteins 0.000 description 1
- 241001414720 Cicadellidae Species 0.000 description 1
- 241000207199 Citrus Species 0.000 description 1
- 241000254173 Coleoptera Species 0.000 description 1
- 241000256054 Culex <genus> Species 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical class CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 241000258937 Hemiptera Species 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- 241000593806 Phyllis Species 0.000 description 1
- 241000500437 Plutella xylostella Species 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 241001454293 Tetranychus urticae Species 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 125000003302 alkenyloxy group Chemical group 0.000 description 1
- 125000005108 alkenylthio group Chemical group 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 description 1
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000005093 alkyl carbonyl alkyl group Chemical group 0.000 description 1
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 description 1
- 125000005197 alkyl carbonyloxy alkyl group Chemical group 0.000 description 1
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 1
- 125000006350 alkyl thio alkyl group Chemical group 0.000 description 1
- 125000005133 alkynyloxy group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000001769 aryl amino group Chemical group 0.000 description 1
- 125000005129 aryl carbonyl group Chemical group 0.000 description 1
- 125000000958 aryl methylene group Chemical group 0.000 description 1
- 125000005110 aryl thio group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 1
- HUHMXYOWQLTPGG-UHFFFAOYSA-N butyl 4-(bromomethyl)benzoate Chemical compound CCCCOC(=O)C1=CC=C(CBr)C=C1 HUHMXYOWQLTPGG-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000073 carbamate insecticide Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 125000004966 cyanoalkyl group Chemical group 0.000 description 1
- 125000000000 cycloalkoxy group Chemical group 0.000 description 1
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- WZPMZMCZAGFKOC-UHFFFAOYSA-N diisopropyl hydrogen phosphate Chemical compound CC(C)OP(O)(=O)OC(C)C WZPMZMCZAGFKOC-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 244000013123 dwarf bean Species 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000004692 haloalkylcarbonyl group Chemical group 0.000 description 1
- 125000004995 haloalkylthio group Chemical group 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000003544 oxime group Chemical group 0.000 description 1
- 125000000466 oxiranyl group Chemical group 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 238000003359 percent control normalization Methods 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- QMYDVDBERNLWKB-UHFFFAOYSA-N propane-1,2-diol;hydrate Chemical compound O.CC(O)CO QMYDVDBERNLWKB-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000005554 pyridyloxy group Chemical group 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- UGJCNRLBGKEGEH-UHFFFAOYSA-N sodium-binding benzofuran isophthalate Chemical compound COC1=CC=2C=C(C=3C(=CC(=CC=3)C(O)=O)C(O)=O)OC=2C=C1N(CCOCC1)CCOCCOCCN1C(C(=CC=1C=2)OC)=CC=1OC=2C1=CC=C(C(O)=O)C=C1C(O)=O UGJCNRLBGKEGEH-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- CMQCNTNASCDNGR-UHFFFAOYSA-N toluene;hydrate Chemical compound O.CC1=CC=CC=C1 CMQCNTNASCDNGR-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野］
本発明は、新規なピラゾールオキシム誘導体および該誘
導体を有効成分として含有する殺虫、殺ダニ、殺菌剤に
関するものである。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to a novel pyrazole oxime derivative and an insecticide, acaricide, and bactericide containing the derivative as an active ingredient.
従来ピラゾールオキシム誘導体に関してはヨーロッパ公
開特許第２３４０４５号公報において殺虫、殺ダニ、殺
菌剤の有効成分として有用であることが開示されている
が、ピラゾール環の３位の置換基がアルキル基、ハロア
ルキル基またはフェニル基に限定されていて、本発明化
合物とはその化学構造面において異なるものである。Conventionally, pyrazole oxime derivatives have been disclosed in European Patent Publication No. 234045 as being useful as active ingredients for insecticides, acaricides, and fungicides. Alternatively, it is limited to a phenyl group, and differs from the compound of the present invention in its chemical structure.
〔発明の態様〕
本発明は、新規なピラゾールオキシム誘導体および該誘
導体を有効成分として含有する優れた殺虫、殺ダニ、殺
菌剤に関するものである。すなわち本発明は、一般式〔
ＩＩ ：
〔式中Ｒは、炭素数１〜６のアルキル基、炭素数２〜６
のアルケニル基、炭素数２〜６のアルキニル基、炭素数
３〜６のシクロアルキル基またはフェニル基を表し、
Ｒ１はハロゲン原子、炭素数１〜４のアルコキシ基、炭
素数１〜４のアルコキシカルボニル基、シアノ基または
ニトロ基を表し、
Ｒ２は、水素原子、炭素数１〜４のアルキル基また。は
フェニル基を表し、
Ｘは、酸素原子または硫黄原子を表し、Ｙは、水素原子
、ハロゲン原子、炭素数１〜６のアルキル基、炭素数１
〜４のハロアルキル基、炭素数１〜４のアルコキシ基、
炭素数１〜４のハロアルコキシ岱、炭素数１〜３のアル
キレンジオキシ基、フェノキシ基、−５（０）、ｌＲ”
基（但し、Ｒ３は炭素数１〜４のアルキル基または炭素
数１〜４のハロアルキル基を示し、ｎは０．１または２
を表す。） 、−ＣＯＯＲ’基（但し、Ｒ４は炭素数１
〜６のアルキル基、炭素数３〜６のシクロアルキル基ま
たは炭素数２〜６のアルケニル基を表す。）ま立に水素
原子または炭素数１〜６のアルキル基を表す。）を表し
、
ｍは１，２または３を表し、
Ａは、−ＣＨ−基、−ＣＩｌ−Ｃ１ｌ−基、−ＣＩＩＣ
ＨＣＨ−基、ｌ ＩＩ ｌ１ｌ
Ｒ？ Ｒ？ Ｒ１１Ｒ７Ｒ８Ｒ９−ＣｌｌＣｌ＋
−０−店、−ＣＩ−Ｃ＝Ｃ−基、（但し、Ｒ７，Ｒ８お
ＩＩ Ｉ １１
Ｒ７Ｒ１１Ｒ７ＲＩＩＲ９
よびＲ９はそれぞれ独立に水素原子または炭素数１〜４
のアルキル基を表す。）を表し、Ｑは、置換されていて
もよいフェニル基または置換されていてもよい複素環基
を表す。〕で表されるピラゾールオキシム誘導体並びに
該誘導体の１種または２種以上を有効成分として含有す
ることを特徴とする殺虫、殺ダニ、殺菌剤に関するもの
である。[Aspects of the Invention] The present invention relates to a novel pyrazole oxime derivative and an excellent insecticide, acaricide, and fungicide containing the derivative as an active ingredient. That is, the present invention is based on the general formula [
II: [In the formula, R is an alkyl group having 1 to 6 carbon atoms, 2 to 6 carbon atoms
represents an alkenyl group, an alkynyl group having 2 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or a phenyl group, and R1 is a halogen atom, an alkoxy group having 1 to 4 carbon atoms, or an alkoxycarbonyl group having 1 to 4 carbon atoms. R2 represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a cyano group or a nitro group. represents a phenyl group, X represents an oxygen atom or a sulfur atom, Y represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 6 carbon atoms, and 1 carbon number.
-4 haloalkyl group, alkoxy group having 1 to 4 carbon atoms,
Haloalkoxy group having 1 to 4 carbon atoms, alkylenedioxy group having 1 to 3 carbon atoms, phenoxy group, -5(0), 1R"
group (wherein, R3 represents an alkyl group having 1 to 4 carbon atoms or a haloalkyl group having 1 to 4 carbon atoms, and n is 0.1 or 2
represents. ), -COOR' group (however, R4 has 1 carbon number
~6 alkyl group, a cycloalkyl group having 3 to 6 carbon atoms, or an alkenyl group having 2 to 6 carbon atoms. ) represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. ), m represents 1, 2 or 3, A is -CH- group, -CIl-C1l- group, -CIIC
HCH- group, l II l1l R? R? R11R7R8R9-CllCl+
-0- store, -CI-C=C- group, (However, R7, R8, II I11 R7R11R7RIIR9 and R9 are each independently a hydrogen atom or a carbon number of 1 to 4
represents an alkyl group. ), and Q represents an optionally substituted phenyl group or an optionally substituted heterocyclic group. The present invention relates to pyrazole oxime derivatives represented by the following formulas, as well as insecticidal, acaricidal, and bactericidal agents containing one or more of these derivatives as active ingredients.
本発明者らは、上記一般式（１）で表される本発明化合
物が優れた病害虫防除作用を有することを見いだしたも
のであり、更に具体的には農業用殺虫、殺ダニ、殺菌剤
、衛生害虫防除剤および動物に寄生するダニの駆除剤と
して極めて有用であることを見出し本発明を完成した。The present inventors have discovered that the compound of the present invention represented by the above general formula (1) has an excellent pest control effect, and more specifically, it can be used as an agricultural insecticide, acaricide, fungicide, The present invention was completed based on the discovery that the present invention is extremely useful as a sanitary pest control agent and as an agent for killing mites parasitic on animals.
上記一般式（１）において、Ｑにおいて定義されている
置換されていてもよい置換基の種類としては、例えば下
記のものが挙げられる。In the above general formula (1), examples of the optionally substituted substituent defined for Q include the following.
ハロゲン原子、アルキル基、アルケニル基、アルキニル
基、アルコキシ基、アルケニルオキシ基、アルキニルオ
キシ基、アルキルチオ基、アルケニルチオ基、アルキル
スルフィニル基、アルキルスルホニル基、シクロアルキ
ルオキシ基、ハロアルキルチオ基、アルキルアミノ基、
アルキルカルボニルアミノ基、ニトロ基、シアノ基、水
酸基、アルキルカルボニル基、アルコキシカルボニル基
、カルボキシル基、アルキルカルボニルオキシ基、アル
コキシカルボニルアミノ基、オキシム基、Ｏ−アルキル
イミノ基、オキシラン基、置換されていてもよいシクロ
アルキル基、アリール基、アリールオキシ基、アリール
チオ基、アリールアミノ基、アリールカルボニル基、ア
リールメチレンオキシ基、アリールオキシメチル基、ア
リールメチレンカルボニル基、アリールメチレン基（但
し上記のアリールは置換されていてもよいフェニル基を
意味する。）、置換されていてもよい複素環基、置換さ
れていてもよいピリジルオキシ基、ヒドロキシアルキル
基、アルキルカルボニルオキシアルキル基、アルコキシ
アルキル基、アルキルチオアルキル基、アルキルカルボ
ニルアルキル基、アルコキシカルボニルアルキル基、シ
アノアルキル基、ハロアルキルカルボニル基などである
。Halogen atom, alkyl group, alkenyl group, alkynyl group, alkoxy group, alkenyloxy group, alkynyloxy group, alkylthio group, alkenylthio group, alkylsulfinyl group, alkylsulfonyl group, cycloalkyloxy group, haloalkylthio group, alkylamino group ,
Alkylcarbonylamino group, nitro group, cyano group, hydroxyl group, alkylcarbonyl group, alkoxycarbonyl group, carboxyl group, alkylcarbonyloxy group, alkoxycarbonylamino group, oxime group, O-alkylimino group, oxirane group, substituted cycloalkyl group, aryl group, aryloxy group, arylthio group, arylamino group, arylcarbonyl group, arylmethyleneoxy group, aryloxymethyl group, arylmethylenecarbonyl group, arylmethylene group (however, the above aryl is substituted) ), an optionally substituted heterocyclic group, an optionally substituted pyridyloxy group, a hydroxyalkyl group, an alkylcarbonyloxyalkyl group, an alkoxyalkyl group, an alkylthioalkyl group, Examples include an alkylcarbonylalkyl group, an alkoxycarbonylalkyl group, a cyanoalkyl group, and a haloalkylcarbonyl group.
これらの置換基は、重複して置換されていてもよい。These substituents may be redundantly substituted.
また、Ｑにおける置換されていてもよい複素環基として
は例えば、下記のものが挙げられる。Furthermore, examples of the optionally substituted heterocyclic group in Q include the following.
チオフェン、フラン、ビロール、イミダゾール、チアゾ
ール、オキサゾール、ピラゾール、ピリジン、ピリダジ
ン、ピリミジン、ピラジン、ベンズオキサゾール、ベン
ゾチアゾール、ベンゾチオフェン、ジベンズチオフェン
、ベンゾフラン、ベンゾイミダゾール、インドール、イ
ンダゾール、キノリン、イソキノリン、キノキザリンな
どである。Thiophene, furan, virol, imidazole, thiazole, oxazole, pyrazole, pyridine, pyridazine, pyrimidine, pyrazine, benzoxazole, benzothiazole, benzothiophene, dibenzthiophene, benzofuran, benzimidazole, indole, indazole, quinoline, isoquinoline, quinoxaline, etc. It is.
置換基を有する複素環基におけるその置換基としては、
例えば、下記のものが挙げられる。As the substituent in the heterocyclic group having a substituent,
Examples include the following:
ハロゲン原子、アルキル基、アルコキシ基、アルキルチ
オ基、アルキルスルホニル基、ハロアルキル基、ハロア
ルコキシ基、ニトロ基、シアノ基、水酸基、アルキルカ
ルボニル基、アルコキシカルボニル基、フェニル基、置
換されていてもよいアリール基などである。Halogen atom, alkyl group, alkoxy group, alkylthio group, alkylsulfonyl group, haloalkyl group, haloalkoxy group, nitro group, cyano group, hydroxyl group, alkylcarbonyl group, alkoxycarbonyl group, phenyl group, optionally substituted aryl group etc.
次に本発明化合物の製造法について説明する。Next, a method for producing the compound of the present invention will be explained.
（Ａ法） Ｒ２
本発明化合物（１）
（Ｂ法）
本発明化合物（１）
〔式中（Ａ法〜Ｂ法）において、Ｒ，Ｒ皿、Ｒ１、Ｘ、
Ｙ、 、Ａ、およびＱは前記と同じ意味を表し、１１ａ
１ はハロゲン原子を表す。〕
反応式Ａ法で示される反応においては、溶媒としては低
級アルコール類（例えばメタノール、エタノール等）、
ケトン類（例えば、アセトン、メチルエチルケトン等）
、炭化水素類（例えば、ヘンゼン、トルエン等）、エー
テル類（例えば、イソプロピルエーテル、テトラヒドロ
フラン、１，４−ジオキサン等）、アミド類（例えばＮ
、Ｎ−ジメチルホルムアミド、ヘキサメチルホスホリッ
クトリアミド等）、ハロゲン化炭化水素類（例えばジク
ロロメタン、ジクロロエタン等）を使用することができ
る。Ｂ法の反応においてもケトン類を除（Ａ法と同じ溶
媒を使用することができる。また必要に応じて、これら
の溶媒の混合溶媒や水との混合溶媒も使用することがで
きる。(Method A) R2 Compound of the present invention (1) (Method B) Compound of the present invention (1) [In the formula (Method A to Method B), R, R plate, R1, X,
Y, , A, and Q represent the same meanings as above, and 11a
1 represents a halogen atom. ] In the reaction shown by reaction formula A method, lower alcohols (e.g. methanol, ethanol, etc.) are used as solvents,
Ketones (e.g. acetone, methyl ethyl ketone, etc.)
, hydrocarbons (e.g., Hensen, toluene, etc.), ethers (e.g., isopropyl ether, tetrahydrofuran, 1,4-dioxane, etc.), amides (e.g., N
, N-dimethylformamide, hexamethylphosphoric triamide, etc.), halogenated hydrocarbons (for example, dichloromethane, dichloroethane, etc.) can be used. In the reaction of Method B, ketones are removed (the same solvent as in Method A can be used. If necessary, a mixed solvent of these solvents or a mixed solvent with water can also be used.
塩基としては、無機塩基（例えば、水素化ナトリウム、
水酸化ナトリウム、水酸化カリウム、炭酸ナトリウム、
炭酸カリウム、炭酸水素ナトリウム等）および有機塩基
（例えば、ナトリウムメトキサイド、ナトリウムエトキ
サイド、トリエチルアミン、ピリジン等）を用いること
ができる。また、必要に応じて、反応系にテトラアンモ
ニウム塩（例エバ、トリエチルベンジルアンモニウムク
ロライド等）を触媒として添加してもよい。反応温度と
しては、−２０°Ｃがら、反応に使用する溶媒の沸点ま
での範囲を設定することができるが、−５゛Ｃから反応
に使用する溶媒の沸点の範囲がより望ましい。原料のモ
ル比は任意に設定できるが、等モルまたは、それに近い
比率で反応を行うのが有利である。Bases include inorganic bases (e.g. sodium hydride,
Sodium hydroxide, potassium hydroxide, sodium carbonate,
Potassium carbonate, sodium bicarbonate, etc.) and organic bases (eg, sodium methoxide, sodium ethoxide, triethylamine, pyridine, etc.) can be used. Further, if necessary, a tetraammonium salt (eg, EVA, triethylbenzylammonium chloride, etc.) may be added to the reaction system as a catalyst. The reaction temperature can be set in the range from -20°C to the boiling point of the solvent used in the reaction, but it is more preferably in the range from -5°C to the boiling point of the solvent used in the reaction. Although the molar ratio of the raw materials can be set arbitrarily, it is advantageous to carry out the reaction at an equimolar ratio or a ratio close to it.
更に詳しくは、（Ａ法）では一般式（ｎ）で表される化
合物を一般式（ＩＩ［）で表されるハライド類と、塩基
存在下で適切な溶媒中で反応させることによって本発明
化合物（Ｉ）を製造できる。More specifically, in (Method A), the compound of the present invention is prepared by reacting the compound represented by the general formula (n) with the halide represented by the general formula (II[) in an appropriate solvent in the presence of a base. (I) can be produced.
ｔｌａｌはハロゲン原子、殊に塩素原子、臭素原子が好
ましい。溶媒としてはＮ、Ｎ−ジメチルホルムアミド、
メタノール、エタノール、トルエンおよびトルエン−水
の混溶媒が好ましく、塩基としては無機塩基が好ましく
、殊に炭酸ナトリウム、炭酸カリウム、水酸化ナトリウ
ム、水酸化カリウムが好ましく、反応温度としては、２
０°Ｃから１００°Ｃが好ましい。tlal is preferably a halogen atom, particularly a chlorine atom or a bromine atom. As a solvent, N,N-dimethylformamide,
Methanol, ethanol, toluene, and a toluene-water mixed solvent are preferred; the base is preferably an inorganic base; sodium carbonate, potassium carbonate, sodium hydroxide, and potassium hydroxide are particularly preferred; the reaction temperature is 2.
Preferably it is from 0°C to 100°C.
本発明化合物を純化する必要が生じた場合は、常法の精
製方法（再結晶、カラムクロマトグラフィー等）によっ
て分離・精製する。When it becomes necessary to purify the compound of the present invention, it is separated and purified by conventional purification methods (recrystallization, column chromatography, etc.).
本発明に包含される化合物としては、具体的には例えば
後記の第１表に示す化合物が挙げられる。Specific examples of the compounds included in the present invention include compounds shown in Table 1 below.
ただし、第１表の化合物は例示のためのものであって、
本発明はこれらのみに限定されるものではない。〔ただ
し、表中、Ｍｅはメチル基を、Ｅｔはエチル基を、Ｐｒ
はプロピル基を、Ｂｕはブチル基を、Ｐｅｎはペンチル
基を、Ｈｅｘはヘキシル基、ｔはターシャリ−を、Ｓは
セカンダリ−を、ｉはイソを示す。〕
なお、本発明の包含される化合物の中で不斉炭素原子を
有する化合物の場合には、光学活性な化合ｍ （＋）体
および（−）体も含むものである。However, the compounds in Table 1 are for illustrative purposes only, and
The present invention is not limited to these. [However, in the table, Me represents a methyl group, Et represents an ethyl group, and Pr represents a methyl group.
represents a propyl group, Bu represents a butyl group, Pen represents a pentyl group, Hex represents a hexyl group, t represents tertiary, S represents secondary, and i represents iso. ] Among the compounds included in the present invention, in the case of a compound having an asymmetric carbon atom, the optically active compound m (+) form and (-) form are also included.
さらに本発明に包含される化合物の中で、立体配置異性
体が存在する場合には、ｃｉｓ体およびｔｒａｎｓ体も
含むものである。Furthermore, when configurational isomers exist among the compounds included in the present invention, cis and trans isomers are also included.
（以下余白）
第 １ 表
ｇ
化合物において
Ｍｅ ＣＩ！、Ｉｔ ＯＩＩ Ｃ１１ｚ Ｐ
ｈＭｅ Ｃｊ！ ＩＩ ＯＨＣ１１ｚ Ｃ６
Ｈ４Ｆ−４Ｍｅ ＣＩ Ｉｔ ＯＩＩ Ｃ１
１ｚ Ｃｂｌ１４Ｃｊ！−２Ｍｅ ｃｚ ＩＩ
ＯＩＩ ＣＨｚ Ｃ，ｌ＋、ＣＩ！、−３Ｍｅ
ｃｚ Ｉｔ ＯＨＣｌＩ２ ＣｂＨａＣＩ
！−４Ｍｅ ＣＩ ＩＩ ＯＩｔ Ｃ１１ｚ
ＣａｌｌＪｒ−４Ｍｅ ＣＩ ＩＩ ＯＩ
Ｉ Ｃ１１ｚ Ｃａｌｌａｌ−４Ｍｅ ＣＩ
Ｉｌ ＯＩｆ Ｃ１ｈ Ｃ６８３Ｐ！−２，６
Ｍｅ ＣＩ Ｉｆ ＯＩＩ Ｃ１１ｚ Ｃ
６１１３Ｃ１２−２，４Ｍｅ ＣＩ ＨＯＩＩ
Ｃｌ１２ ＣｂｌｌｚＣｌ、ｚ−３，４Ｍｅ Ｃ／
！ ＩＩ ＯＨＣＨｚ ＣｂｌｌＪｒｚ−３，
５Ｍｅ ＣＩ ＨＯＨＣ１１ｚ Ｃ，）Ｉ：＋Ｆ
−３，Ｃｊ！−４ＲＲ’ Ｒ２Ｘ ＹＩＩＡ
ＱＭｅ ｃ！！、ＨＯＩＩ Ｃ１１
ｚ ＣＪｎＥｔ−３ＣＨＣｉ！、Ｉｔ ＯＩＩ
ＣｌＩ２ ＣｂＨａＰｒ−４Ｍｅ ＣＩ
Ｉｆ ＯＩｔ ＣｌＩ２ ｃ６１１４
ｐｒ−ｔ−２ＣＨＣＩ Ｉｆ ＯＨＣＨｚ
ＣＪＩ４Ｐｒ−ｉ−４Ｍｅ ＣＩ Ｉｔ
ＯＩｔ Ｃｌ１ｚ ＣＪＪｕ−３ＣＨＣＩ
ＨＯＩＩ Ｃｌ１ｚ ＣＪＪｕ−４Ｍｅ
ＣＩ２ ＩＩ Ｏｌｌ Ｃｌ１２ Ｃ
６Ｃ６１１ｎＢｕ−ｉ−４ＣＩ ＩＩ ＯＨＣ
ＩＩＺ Ｃ６Ｃ６１１４ＢＩＩ−５−４Ｃｆ
ＩＩ ＯＩＩ Ｃｌｈ ＣＪＪｕ−ｔ−２
ＣＨＣＩ ＩＩ ＯＩＩ Ｃｌｈ Ｃ
６ＨＪｕ−ｔ−３ＣＨＣｆｆ Ｉｔ ＯＩＩ
Ｃ１ｈ Ｃ６Ｃ６１１Ｊｕ−ｔ−４Ｃｊｌ：
ＩＩ ＯＨＣＨｚ Ｃ６Ｈ４Ｐｅｎ−４Ｍ
ｅ ＣＩＩＺ ｔｌ ＯＩｆ ＣｌＩ２
ＣＪＩ４Ｐｅｎ−ｓ−４Ｍｅ Ｃｆｆ Ｉ
Ｉ ＯＩｔ Ｃｌ１ｚ ＣＪＩ４Ｐｅｎ−
ｔ−４Ｍｅ Ｃ１ＩＩ Ｏ！！ Ｃｌ１ｚ
Ｃ６１１３Ｃ−ｅ−３＋Ｂｕ−ｔ−４Ｍｅ ＣＩ
Ｉｔ ＯＩＩ Ｃ１１ｚ Ｃ６１Ｉ
、Ｍｅ−３，Ｂｕ−ｔ−４Ｍｅ Ｃｆ Ｈ
ＯＩｆ Ｃｌｈ Ｃ６１１２Ｍ１３２二２
．５．Ｐｒ−４Ｍｅ ＣＩ２ ＨＯＨＣＨｚ
ＣｂＨａ−ＣＭｅｚＣＮ−４ＲＲ’ Ｒ”Ｘ
ＹＩ、ｌＡ ＱＭｅ ＣＩＩＺ ）
！ ＯＩＩ Ｃ１（Ｚ Ｃ６Ｈ４−（Ｃ２）
−４Ｍｅ Ｃ１ｔｌ Ｏｔｌ ＣＨ２Ｃ＆＋（
４−（Ｑ３−ＣＮ−１）−４Ｍｅ Ｃｆ ＨＯｔｌ
ＣｌＩ２ Ｃ６Ｃ６１１４−（Ｑ４）−４ＣＩ
Ｉｔ ＯＨＣＨ２Ｃ６Ｈ４−（Ｃ５）−４Ｍｅ
Ｃ４！ ＩＩ ＯＩＩ Ｃ１１ｚ Ｃ
１，８４−（Ｃ６）−４Ｍｅ ＣＩ ＨＯＨＣ１ｂ
Ｃ６Ｃ６Ｈ４−８１３Ｘ−４ＣＩ ＩＩ
ＯＨＣＨｚ Ｃ６Ｃ６１１ａ−Ｐｈ−４ｃｉ！、Ｉ
Ｉ ＯＨＣ８２Ｃ，ＩＩ、−（Ｃ６Ｈ４Ｆ−４）−
４Ｍｅ ＣＩＩＺ Ｉｆ Ｏｌｌ ＣＨ２Ｃ
６Ｈ４−（Ｃ，Ｈ４ＣＩ２−４）−４Ｍｅ ＣＩ
ＩＩ ＯＩＩ Ｃｌ１２ Ｃ６Ｈ４−（Ｃ６
Ｈ４ＣＦ：ｌ−１−４）−４ＣＩ Ｉｔ ＯＩｔ
Ｃｌ１２ Ｃｉ、ＩＬ−ＣＭｅｚＯＭｅ−４Ｍ
ｅ Ｃｆｆ ＨＯＨＣｌ１ｚ Ｃ６Ｑａ−（ＣＨ
＝ＣＨ−ＣＯＢｕ−ｔ）−４Ｍｅ ＣＩ Ｉｆ
ＯＨＣＨｚ Ｃ＝）Ｉ４−（ＣＩＩ＝Ｃｌｌ−Ｃ
ＯＯＥｔ）−４Ｍｅ ＣＩ ＨＯＨＣＨｚ Ｃ
６１１ｎ−（ＣＩ（＝ＣＢｒｚ）−４ＦＩｅ ＣＩ
ＨＯＨＣＨｚ ＣａＨ４−ＣＭｅｚＣＯＯＥｔ−
４Ｍｅ ＣＩ ＨＯＨＣＨｚ Ｃ６Ｃ６Ｈ４Ｃ
００ｌ１−４ ＣＩ Ｉｔ ＯＩＩ ＣＨｚ
Ｃｂｌｌ、ＣＯＯＭｅ−４Ｍｅ ＣＩ Ｉｔ
ＯＨＣＨｚ Ｃ６Ｃ６１１４ＣＯＯＥｔ−２
Ｃｉ！、Ｉｔ ＯＩｔ Ｃｌ１ｚ Ｃａ１ｌ
＜Ｃ００Ｅｔ−３ＲＲ’ Ｒ”Ｘ ＹＩ、ｌＡ
ＱＭｅ ＣＩ！、ＩＩ Ｏｉｔ
ＣＨ，Ｃ６Ｃ６１１４ＣＯＯＥｔ−４ＣＩ２ ＨＯ
ＨＣＨｚ ＣＪｎＣＯＯＰｒ−４Ｍｅ ＣＩ
ＩＩ ＯＨＣｔｌｚ Ｃ６ｔｌａＣＯＯＰｒ−
ｉ−２ＣＨＣＩ ＩＩ ＯＨＣｌＩ２ Ｃ６
１１ＣＯＯＰｒ−ｉ−３ＣＨＣ１ｔｌ ＯＩＩ
ＣｌＩ２ Ｃ６Ｃ６１１ｎＣＯＯＰｒ−ｉ−４ＣＩ
ＨＯｔＩ Ｃｌ１２ Ｃ６Ｃ６１１ｎＣＯ
ＯＢＩＩ−４ＣＩ２ ＩＩ ＯＨＣＬ Ｃ
６４ＣＯＯＢｕ−ｉ−４Ｍｅ ＣＩ２ ＨＯＨＣ１
１ｚ Ｃ６ｔｌａＣＯＯＢｕ−ｓ−４Ｍｅ ＣＩ
Ｉｆ ＯＩｆ Ｃｌ１２ Ｃ，、ＩＩｌ
ＩｎＣｏｏＢｕ−ｔ−２（／２ Ｉｔ ＯＨＣＨ
ｚ Ｃ６Ｃ６Ｈ４Ｃ００Ｂｕ−ｔ−３ＣＩ ＨＯ
ＨＣｔｌｚ Ｃａｌ１４ＣＯＯＢｕ−ｔ−４Ｍｅ
ＣＩ Ｉｔ ＯＩＩ Ｃ）ｌｚ ＣＪｎ
ＣＯＯＰｅｎ−ｔ−３ＣＨＣＩ Ｉｔ Ｏ１１
Ｃ１１２Ｃｉ、ＩｌｌｌｎＣｏｏＰｅｎ−ｔ−４Ｃｆ
ＩＩ ＯＨＣ１１ｚ ＣａＣａｌｌｎＣ００
ＣＨＥｔｚ−４Ｃｊ！ Ｉｔ ＯＩｆ ＣＨ２
Ｃ６Ｃ６１１４Ｃｏｏ（Ｑ３）−４ｃｚ ）Ｉ
ＯＨＣ１ｈ Ｃ，Ｉｌ、ＣＯＯ（Ｑ３−ＭｅＣｏｏ
（Ｑ３− ＣＩ Ｉｔ ＯＩＩ Ｃｔ（ｚ
Ｃ６１４ＣＯＯＣＭｅｚＣＩＩ＝Ｃ６Ｈ４Ｃ００Ｃ
”、ｆｆｉ ＨＯＩＩ Ｃ１１ｚ Ｃ６Ｃ６１
１４ＣＯＯＩＩｅｘ−４ＣＩ Ｉｔ ＯＩｔ
Ｃ１１□Ｃ６１１，ＣＯＯＣＭｅｚＰｒ−Ｃ００ＣＲ’
Ｒ２Ｘ Ｙｌ、ｌ 八
ロＭｅ ＣＩ ＨＯＨＣ１１２Ｃ６１１４
ＣＣ６１１４ＣＯＯＣＥｔ２ Ｃｊ！ ＨＯＨＣ
１（ｚ ＣａＨ，ＣＯＯＣＨＭｅＢｕ−Ｃ００ＣＨ
Ｃ１Ｉｔ ＯＨＣｔｂ Ｃ６１１４ＣＯＯ
−（口４）−４Ｍｅ Ｃ１！、ＨＯｔｌ Ｃｔｌｚ
Ｃ６Ｈ４ＣＯＯ−（Ｃ６Ｈ４Ｃ０Ｏ−（Ｑ４−
ＣＩ ＨＯＨＣｌ１ｚ Ｃ６１１，ＣＯＯ−（
Ｃ００−（Ｑ４−．６）−４Ｍｅ ＣＩ ＨＯＨＣ
ｌＩ２ Ｃ６Ｃ６１１４ＣＯＯ−（Ｃ６）−４Ｃｆ
ＨＯＩｔ Ｃ１１２Ｃ６Ｈ４ＣＯＯＣｔｌ（Ｐｒ
−ｉ）ｚ−４Ｍｅ Ｃｆ ＨＯＩｔ ＣｌＩ２
Ｃ６１１ａＣＯＯＣＥｔ＊−４Ｍｅ ＣＩ
ＨＯＩｔ Ｃｌ１ｚ Ｃ６Ｈ４Ｃ０ＯＣＩＩＭｅ
Ｐｈ−４Ｍｅ ＣＩ ＨＯＩｆ Ｃｌ１２
Ｃｔ、Ｈ４Ｈ４Ｃ００Ｃｚｌ１４０Ｐｈ−４ＣＩ
ＩＩ ＯＨＣｌＩ２ Ｃ６１１ｎＣＣ６１１
ｎＣＯＯＣｚＨ４０ＣＩ Ｉｔ ＯＩｔ Ｃ
ｌ１２ ＣＪ４ＣＯＯＣＭｅｚＣＩＩｚＯＭｅ−４
Ｍｅ ＣＩ ＩＩ ＯＨＣＨｚ Ｃ６１
１ＣＯＯＣＭｅｚＣＯＯＭｅ−４Ｍｅ ＣＩ ＨＯ
ＨＣＨｚ ＣＪ４ＣＯＯＣＨｚＣｈ−４Ｍｅ Ｃ
Ｉ ＨＯＨＣ１ｂ Ｃ６１１４ＣＯＯＣ１ｌ（Ｃ
Ｆ＋）ｚ−４Ｍｅ ＣＩ ＨＯＨＣＨ２ＣＪｎＣＯ
ＯＣＩＩ（Ｃ１ｌｚＣｆ）ｚ−４Ｍｅ ＣＡ Ｉ
Ｉ ＯＨＣ１ｈ Ｃ６１１４ＣＯＯＣ６１１４
ＣＯＯＣ，ｅ−４Ｍｅ Ｃｌ２ Ｉｆ ＯＩ
Ｉ ＣＨ２Ｃ６４ＣＯＯＰｈ−４Ｍｅ Ｃ１ｔｌ
ＯＨＣｌ１ｚ Ｃ６１１４ＣＯＯ（Ｃ６ＩＩｎ
Ｃｊｌ！−４Ｌ４ＲＲ’ Ｒ２Ｘ Ｙｆｆｉ
Ａ ＱＭｅ ＣＩ２ ＩＩ Ｏ
ｔｌ Ｃ１１ｚ Ｃ６１１：＋Ｃｊ２−３．ＣＯ
Ｃ００Ｂｕ−ｔ−４ＣＥ ＩＩ ＯＨＣｌ１ｚ
Ｃ６１１Ｃ６１１４ＣＯ５門ｅ Ｃｆ Ｉ
ｔ ＯＩｔ Ｃｌ１ｚ Ｃｔ、Ｉ１４ＣＯＳ
Ｅｔ−４Ｍｅ ＣＩ Ｉｆ ＯＩｔ Ｃｌ
ｈ Ｃ６Ｃ６１１４ＣＯＳＰｒ−ｉ−４Ｃｉ Ｉ
ｔ ＯＩｔ Ｃｌ１２ Ｃ７１１４ＣＯ３Ｂ
ｕ−ｔ−４Ｍｅ Ｃｅ Ｉｔ ＯＩｔ Ｃ
１１ｚ Ｃ６１１ｎＣＣ６１１ｎＣＯＮＨＣＩ
Ｉｔ ＯＩｔ Ｃ１１ｚ ＣＪＩ４ＣＯＮ
ＨＰｒ−ｉ−４Ｍｅ ＣＩ２ Ｉｔ ＯＩＩ
Ｃ１１ｚ ＣｂＩＩ＜ＣＯＮＩＩＢｕ−ｔ−４
Ｍｅ ＣＩ２ ＩＩ ＯＨＣ１１ｚ Ｃ
６１１４ＣＯＣ６１１４ＣＯＮ Ｃｆ ＩＩ
ＯＩＩ Ｃ１１ｚ ＣＪ４ＣＯＮ（Ｐｒ−ｉ）
ｚ−４Ｍｅ ＣＩ Ｉｔ Ｏ’Ｉｔ Ｃ１
１ｚ Ｃ６１ＬＣＯＮＭＣ６１ＬＣＯＮ Ｃｆｆ
ＩＩ ＯＩｔ Ｃｌ１ｚ Ｃ６１１ｎ
ＣＣ６１１ｎＣＯＣ１ＨＯＩｔ Ｃｌ１ｚ ＣＪ
１４ＣＯＣＯＯＥｔ−４Ｍｅ ＣＩ２ １１ ０
ＩＩ Ｃｌ１ｚ Ｃ６Ｃ６１１４ＣＯＣＯ
ＯＰｒ−ｉ−４Ｃｆ ｔｌ ＯＩｆ Ｃｌ１
２ Ｃｄ１４ＣＯＰｒ−４Ｍｅ ＣＩ ＨＯ
Ｉｆ Ｃ１１ｚ Ｃｄ１４ＣＯＰｒ−ｉ−４Ｍｅ
Ｃ／２ ｔｌ ＯＩＩ Ｃｌ１ｚ
Ｃ６ＨｎＣＯＢｕ−ｔ−３Ｍｅ ＣＩ ＩＩ Ｏ
Ｉｔ ＣＨｚ Ｃ６Ｃ６Ｈ４Ｃ０Ｂｕ−ｔ−４Ｃ１
Ｉｔ ＯＩｔ Ｃ１１ｚ Ｃ６１１４ＣＯＣ
Ｃ６１１４ＣＯＣＲ’ Ｒ２Ｘ Ｙｆｆｉ Ａ
ＱＭｅ ＣＮ ＨＯＩＩ Ｃｌ１
ｚ ＣＪ、ＣＯＣＭｅｚＣＯＯＭｅ−４Ｍｅ Ｃ
Ｉ ＨＯＩＩ ＣＨｚ Ｃｉ、！ｌｉｃＯＰｈ
−４Ｍｅ Ｃ１１１０ＨＣＨ２Ｃ６Ｃ６Ｈ４Ｃ０（Ｃ
６Ｈ４Ｃｆｆｉ−４）−４ＣＩ ＨＯＨＣ１１２ＣＪ
４ＣＯ（Ｃｄ１４ＣＦｉ−４）−４Ｍｅ ＣＩ Ｉ
ｆ ＯＨＣ１１ｚ Ｃ４Ｃ４ｌｌ４ＣＯ（ＣＪ
Ｊｕ−ｔ−４）−４ＣＩ Ｉｔ ＯＩＩ Ｃｌ
１ｚ Ｃ６日Ｊｅｚ−２，６−６−Ｃ０Ｐｈ−４Ｃ
１１１０ＨＣ１１ｚ ＣｈＨ４ＣＯ−（Ｑ９）−４
Ｍｅ ＣＩ Ｉｔ ＯＨＣＨ２Ｃ６Ｃ６１１４
ＣＯ−（ＱＩＯ）−４ＣＩ ＨＯＩｔ ＣＨｚ
Ｃ６１１ｎＣ６１１ｎＣＯ−（ＱＩＯ−，６）−４Ｍ
ｅ Ｃ１１１０ＨＣＨ２Ｃ６Ｈ４−（Ｃ７−Ｍ＋３−
３−２）−４Ｃｊｌ！ ＨＯＨＣＨｚ ＣｂＩＩ
４−（Ｃ７−Ｍｅｚ−２，４）−４Ｍｅ Ｃｊｌ！
Ｉｔ ＯＨＣｌ１２ Ｃ６Ｃ６１１ｎ−（Ｃ
７−Ｅｔ−２）−４ＣＩ ＩＩ Ｏｆｌ Ｃ１
１ｚ Ｃ，ＩＩ４−（Ｑ８−Ｍｅ−２）−４Ｍｅ
ＣＩ Ｉｔ ＯＨＣＨ２Ｃ６Ｃ６１１４−（Ｑ
８−ＣＮ−２）−４ＣＩ Ｈ０１１Ｃｔｌｚ Ｃ
６１１ａ−（Ｑ８Ｃ６１１ａ−（Ｑ８−ＣＯＯＣｊ！
ＩＩ ＯＨＣ１１ｚ Ｃｊ１４０Ｍｅ−４Ｍ
ｅ ＣＩ ＨＯＨＣＨｚ Ｃ６Ｃ６１１４０Ｅ
ｔ−４Ｃ１ＨＯＩＩ Ｃｌ１ｚ Ｃ６Ｃ６１１４
０Ｐｒ−４Ｃ１ＩＩ ＯＨＣ１１ｚ Ｃ６１１
４０Ｐｒ−ｉ−３ＲＲ’Ｒ２Ｘ’ＹＬｌｌ Ａ
ＱＭｅ ＣＩ Ｉｆ 、Ｏ
ＩＩ Ｃ１１ｚ Ｃ６１１４０Ｐｒ−ｉ−４門ｅ
Ｃｆｆ１ ＨＯＩＩ ＣＨ２Ｃ６１１４０Ｂ
ｕ−４門ｅ ＣＩ ＩＩ ＯＩＩ Ｃ１１
ｚ Ｃｂｌｌ＜ＯＢｕ−ｉ−４Ｍｅ Ｃｐ、Ｉｔ
ＯＩｆ Ｃ１，２Ｃ６Ｈ４０ＢＩＩ−３−４Ｍ
ｅ Ｃｆｆ１ Ｉｌ ＯＩＩ ＣＨｚ
Ｃ６Ｃ６１１４０Ｂｕ−ｔ−４ｃｇ ＩＩ ＯＩ
Ｉ Ｃ１１ｚ Ｃ＆＋（４０ＣＩＩＦ２−３Ｍｅ
ＣＩ２ ＩＩ ＯＩｔ ＣｌＩ２ Ｃ
ｂｌｌａＯＣｌｌｈ−４Ｍｅ Ｃ１！、ＩＩ Ｏ
Ｉｆ ＣＨｚ Ｃ，Ｈ４０ＣＦ：ｌ−４Ｍｅ
ＣＩ ＩＩ ＯＩｔ Ｃ１１２Ｃ６１１４０
Ｃ１１２ＣＦ：ｌ−４Ｍｅ ＣＩ！、ＩＩ ＯＩ
ｆ ＣＨ２Ｃ６Ｃ６１１４０ＣＦ２ＣＩＩＦＺ−３Ｃ
ｆｆ１ ＩＩ ＯＩＩ ＣｌＩ２ ＣＪ
４０ＣＦ２ＣＨＦｚ−４Ｍｅ １１２ ＩＩ
ＯＨＣ１１ｚ Ｃ６Ｃ６１１ａＯＰｅｎ−４ＣＩ
Ｉｆ ＯＩＩ Ｃ１１ｚ Ｃ６Ｃ６１
１４０１１ｅｘ−４Ｃｆｆ Ｉｔ Ｏｆｌ
Ｃｌ１ｚ Ｃ６１１ａＯ（０４）−４勤 Ｃｆ
ＩＩ ＯＩＩ ＣＩｌ□ Ｃ６Ｃ６１１４０
Ｐｈ−３ＣＩ！、ＩＩ ＯＩｔ Ｃｌ１ｚ
Ｃ６Ｃ６１１４０Ｐｈ−４Ｃ１１１０ＩＩ Ｃ１１２
Ｃ６１１，０（Ｃ６Ｈ，Ｃｉ−４）−４Ｍｅ ＣＩ
ＩＩ ＯＨＣｌ１２ Ｃｄ１ｎＯ（Ｃ，Ｈ
４ＣＦｚ−４）−４Ｍｅ ｃｘ ＩＩ ＯＩ
Ｉ Ｃ１１ｚ Ｃ６１１ｚ−（ＯＣＩｌｚＯ）−
３，４ＲＲ’ Ｒ２Ｘ Ｙ、％ Ａ
ＱＭｅ ＣＩ ＩＩ ＯＨＣＨｚ Ｃｂ
ｌｌＪｅ−３＋ＯＰｒ−４Ｍｅ ＣＩ Ｉｆ
ＯＨＣｌ１ｚ ＣｂＩＩ４−（ＯＣＩＩｚＣＩｌｚＣ
ＨｚＯＭｅ）−４Ｍｅ ＣＩ２ Ｉｔ
０ １１ ＣｌＩ２ Ｃ６１１，Ｏ−（口
２６−（、ｅ−４，ＣＦＣＦ３−６）−４Ｃｆ ＨＯ
Ｉｔ ＣＨｚ ＣｂＨ４０ＣＨｚＰｈ−４Ｍｅ
ＣＩ Ｉｔ ＯＨＣＨ２Ｃｂ）１．０ＣＩ（ｚ（
Ｃｉ、ＩＩ４−Ｆ−４）−４Ｍｅ ＣＩ ＨＯＩＩ
Ｃｔ（ｚ ＣＪ４０Ｃｌ１ＭｅＣＯＯＥｔ−４Ｍ
ｅ Ｃｆ ＨＯｆｌ Ｃｌ１ｚ Ｃ６ＨｎＣＯ
ＢｕｅＣＯＯＢｕ−ｔ−４Ｍｅ Ｃｆ ＩＩ
ＯＩｔ ＣＨｚ Ｃｂｌ１４０ＣＭｅｚＣＯＯＥｔ
−４Ｍｅ ＣＩ Ｉｔ ＯＨＣＨ２Ｃ６ＨｎＣ
ＯＢｕ−ｔ−４Ｍｅ ＣＩ Ｉｔ ＯＨＣ）Ｉ
ｚ Ｃ６１（ａＯｃＯ１（ａＯｃＯＣＩ ＩＩ
ＯＨＣｌ１ｚ Ｃａｌ１４ＳＭｅ−４Ｍｅ （Ｆ
！ ＨＯＨＣ１１ｚ Ｃ６Ｈ４ＳＯＣ６Ｈ４５ＯＣ
Ｉ Ｉｆ ＯＩｆ ＣＨｚ Ｃｄ１４ＣＯＰ
ｒ−４Ｍｅ Ｃ１ｌｌ ＯＨＣ１１ｚ ＣＪＩ
４ＳＥｔ−４Ｍｅ ＣＩ Ｉｆ Ｏｔｌ Ｃ
ｌ１ｚ ＣＪｌａＳＰｒ−ｉ−２Ｍｅ Ｃ１Ｉｔ
ＯＨＣ１Ｃ１１２ＣＪ１４ＳＰｒ−ｉ−３ＣＩ
ＨＯＩＩ Ｃ１１ｚ Ｃ，、ｆ１４ｓＰｒ−ｉ−４
Ｍｅ ＣＩ ＨＯＨＣＨｚ ＣｂｌｌａＳＯＰｒ
−４−４Ｍｅ ＣＩ ＨＯＨＣ１１ｚ Ｃｉ、Ｉ
Ｉ４ＳＯｚＰｒ−ｉ−４ＲＲ’ Ｉ２２ χ
ＹＩＩＡ ＱＭｅ ＣＩ ＩＩ
ＯＨＣｌＩ２ Ｃｉ、ＩＩｉＳＢｕ−ｔ−４Ｍ
ｅ ＣＩ ＩＩ ＯＩＩ Ｃ１１２Ｃ６Ｃ
６１１４５ＣＩＩＦＺ−３ｃｐ ＩＩ Ｏｔｌ
Ｃ１１ｚ ＣｂｔｌａＳＣＨＦｚ−４Ｍｅ
ＣＩ ＩＩ Ｏｔｌ ＣＨ２Ｃ６Ｃ６Ｈ４５Ｏ
ＣＩＩＦ２−４ ＣＩ２ ＩＩ ＯＩｔ
Ｃ１１ｚ Ｃｄ１４ＳＯ，ＣＨ［’ｚ−４Ｍｅ
ＣＩ２ Ｉｔ ＯＩＩ Ｃｌ１ｚ
Ｃ６Ｃ６１１ｎＳＣＦｚＢｒ−４ＣＩ ＩＩ Ｏ
Ｉｔ ＣｌＩ２ Ｃｉ、ＩＩ４ｓｃｈｃＩＩＦ
ｚ−４Ｍｅ Ｃｆ２ Ｉｔ ＯＩＩ Ｃｌ
１ｚ ＣｂＩｌａＳＯＣＦｚＣＨＦｚ−４Ｍｅ
ＣＩ ＩＩ ＯＨＣＩＩＺ Ｃ６＋１
４ＳＯ２ＣＦ２ＣＩＩＦＺ−４Ｍｅ Ｃ／２ Ｈ
ＯＩ ＣｌＩ２ Ｃ６Ｃ６１１４ＳＣ１１２Ｃ
Ｆ３−４ ＣＩ Ｉｔ ＯＩＩ ＣｌＩ２
Ｃ６Ｃ６１１４ＳＣＦ３−４ ＣＩ！、Ｉｆ
ＯＨＣｌ１２ Ｃ６Ｃ６０４ＣＮ−４ＣＩ
！、ｔｌ ＯＨＣｌＩ２ Ｃ６Ｃ６１１４Ｎ
Ｏ２−４ｃｘ Ｉｔ ＯＩｔ ＣＨｚ
ＣＪＩ４ＳｉＭｅ＋−４Ｍｅ ｃｘ ＩＩ
ＯＩＩ Ｃｌ１ｚ ＣＪｌａＣｈ−４Ｍｅ
ＣＩ ＩＩ ＯＩＩ ＣＨｚ Ｃ６
ＨｎＣＩＩｚＣｊ２−４Ｍｅ ＣＩ Ｈ０１１Ｃ１
ｈ Ｃ６Ｃ６１１ｎＣＨｚＣＩＩｚＢｒ−４ＣＩ
Ｉｆ ＯＨＣｔｌｚ Ｃ１７−ＣＯＯＢ
ｕ−ｔ−５Ｍｅ Ｃ１Ｉｔ Ｏ１１Ｃｌ１ｚ
Ｃ１７−ＯＣＦｚＣＩＩｈ−５ＲＲ’ Ｒ２Ｘ
ＹｌｌｌＡ ＱＭｅ ＣＩ Ｈ
ＯＨＣ１ｈ Ｃ２６−ＣＡ−４−ＣＦｉ−６Ｍｅ
Ｃ１ｔ（ＯＨＣＨｚ Ｃ２６−Ｂｕ−ｔ−６Ｍｅ
ＣＩ ＩＩ ＯＨＣｌ１ｚ Ｃ２６−Ｏ
Ｐｒ−６Ｍｅ ＣＩ２ ＨＯＨＣＨ２Ｃ２６−ＯＣ
ＦｚＣＨＦｚ−６Ｍｅ ｃａ Ｉｔ ＯＨＣＨ
ｚ Ｃ２６−Ｉ−６Ｍｅ ＣＩ Ｉｆ
Ｏｆｌ ＣＨｚ ロ２６−ＱＣ）１．（
Ｃ，Ｈ４Ｈ４Ｆ−４）−６ＣＩ Ｉｔ ＯＩＩ
ＣＬ Ｃ２６−０（Ｃｉ、Ｉ１４Ｃｈ−４）−６Ｍｅ
ＣＩ Ｉｔ ＯＩＩ ＣｌＩ２
ロ２６−ＣＯ０Ｂｕ−Ｌ−６Ｍｅ Ｃｆ
ＨＯｔｌ Ｃ１＋２ ０２３−Ｂｕ−５Ｍｅ
Ｃ１ｌ Ｏｔ（Ｃｔｌｚ （１２３−Ｂｒ
−５Ｍｅ ＣＩ ＨＯＩＩ Ｃｔｌｚ （１
２３−ＣＯＯＰｒ−ｉ−５Ｍｅ Ｃｄ２ ＩＩ
Ｏｔｌ Ｃｌ１ｚ Ｃ２２−ＯＰｒ−ｉ−４Ｍ
ｅ ＣＩ ＨＯｔｌ ＣＨｚ Ｃ２２−ＣＯ
ＯＢｕ−ｔ−５Ｍｅ Ｃ１ｌｌ ＯＮ Ｃ）Ｉ
ｚ Ｃ２４−Ｍｅ−５Ｍｅ ＣＩ２ Ｉｆ
ＯＨＣＨ２Ｇ２５−Ｍｅｚ−２＋４Ｍｅ ＣＩ
ＩＩ ＯＩＩ Ｃｌ１ｚ Ｃ２７−Ｃｆ−６
Ｍｅ ＣＩ ＨＯＨＣＨｚ ０２８Ｍｅ Ｃ
１１１０ＨＣ１１２Ｑ２９
Ｍｅ ＣＩ ＩＩ ＯＨＣｌ１ｚ Ｃ３０
）Ｉ Ｉｔ’ Ｒ２Ｘ ＹｌｌｌＡ
ＱＭｅ ＣＩ Ｉｆ ＯＩｆ
ＣＩＩＺ ロ３１Ｍｅ ＣＩ ＩＩ
ＯＩＩ ＣＨｚ Ｃ３２−Ｍｅ−２Ｍｅ Ｃ
１ｌ（ＯＩＩ Ｃ１１２Ｃ３３−ＣＩ２−５旧 ＣＩ
ＩＩ ＯＨＣＨ２’Ｑ３４−ＣＦ：ｌ−２Ｍｅ
ＣＩ２ Ｉｔ ＯＨＣｔｌｚ Ｑ３５Ｍ
ｅ ＣＩ ＨＯＨＣ１ｈ Ｃ３６−Ｅｔ−２Ｍ
ｅ ＣＱ Ｉｆ Ｏｆｌ Ｃ１１，Ｃ３７−
Ｍｅ−ＩＭｅ ＣＩ！、ｔｌ ＯＩＩ ＣＨｚ
Ｃ３８−Ｍｅ−ＩＭｅ ＣＩ ＩＩ Ｏ
ＩＩ Ｃ１１ｚ Ｃ３９−Ｍｅ−ＩＭｅ ＣＩ
Ｉｔ ＯＨＣＨｚ Ｃ４０−Ｍｅｚ−１，
３Ｍｅ ＣＩ ＨＯｆｆ Ｃ１１２０４１−Ｍｅ
−ＩＭｅ ＣＩ ＨＯＨＣＨｚ Ｃ４２−Ｍｅ
−４Ｍｅ ＣＩ ＨＯｉｔ Ｃ１１ｚ Ｑ４
３Ｍｅ Ｃ１ＨＯｔｌ ＣＨｚ Ｑ４４Ｍｅ
Ｃ１ｔｌ ＯＩ Ｃｔｌｚ Ｃ４５−Ｍｅ−５
Ｍｅ ＣＰ、）Ｉ ＯＩｔ Ｃｌ１ｚ Ｃ４
６−Ｃ１−６Ｍｅ ＣＩ ＨＯＩｆ ＣｌＩ２
Ｃ４６−ＣＦ３−６助 ＣＩ２ ＨＯＨＣ１ｈ
Ｃ４７−ＣＩ２−７ＲＲ’ Ｒ２Ｘ ＹｍＡ
ＱＭｅ ＣＩ ＩＩ ＯＩＩ
Ｃｌ１ｚ Ｃ４９−Ｍｅｚ−２＋４Ｍｅ ＣＩ２
ＩＩ ＯＩＩ Ｃ１１ｚ Ｑ５０Ｍｅ
ＣＩ２ Ｉｔ ＯＩＩ Ｃｌ１ｚ Ｃ
５１−Ｍｅ−５Ｍｅ Ｃ！！、ＨＯＨＣｌＩ２
Ｃ５２−Ｍｅ−５Ｍｅ ＣＩ Ｉｔ ＯＩＩ
Ｃｌｈ Ｃ５３−Ｐｈ−１Ｍｅ ＣＩ ＩＩ
ＯＩｆ Ｃ１ｂ Ｃ５４−Ｍｅ−１，Ｂｕ
−ｔ−３Ｍｅ ＣＩ ＨＯｔｌ Ｃ１１２Ｃ５５
−Ｍｅｚ−２＋６Ｍｅ ＣＩ ＩＩ ＯＩｆ
ＣＨｚ Ｑ５６Ｍｅ （、ｊ！ Ｉｔ
ＯＨＣＨｚ Ｑ５７Ｍｅ Ｃｆ２ Ｉｆ
ＯＩＩ ＣｌＩ２ Ｃｄ４−（Ｑｌｌ）−４Ｍｅ
ＣＩ ＨＯＨＣＨ２Ｃ，Ｈａ−（Ｃ１２）−４Ｍ
ｅ ＣＩ ＩＩ ＯＩｔ Ｃｌｈ Ｃ６
Ｃ６１１４−（Ｃ１３）−４ｃｚ ＨＯＨＣｔｈ
Ｃ６Ｈ４−（口１４）−４Ｍｅ ＣＩ ＨＯ
Ｉｆ ＣＩＩＺ Ｃ＆＋１．−（Ｃ１５）−４Ｍ
ｅ ＣＩ Ｉｔ ＯＨＣＩＩＺ Ｃ＆＋１
４−（Ｃ１６）−４Ｍｅ ＣＩ ＩＩ Ｏｌ（Ｃ
Ｌ ＣＪａＣＬ−（旧１）−４Ｍｅ Ｃ１ＨＯＨＣ
ｌＩ２ Ｃ６Ｃ６１１４ＣＨｚ−（Ｃ１２）−４ｃ
ｐ ＨＯＨＣｌＩ２ Ｃ６Ｈ４ＣＨｚ−（Ｃ１６
）−４Ｅｔ ＣＩ ＨＯｉｔ ＣＬ Ｃ，、
Ｈ４ＣＯＯＢｕ−ｔ−４ＲＲ’ Ｒ２Ｘ ＹＩ
ＩＡ ＱＥｔ Ｃｆ ＩＩ ＯＩ
Ｉ ＣＩＩＺ Ｃ６１１４ＣＯＯ−Ｃ６１１４ＣＯ
Ｏ−（Ｑ４− ＣＩ ＨＯＨＣＩ（ｚ ＣＪＪ
ｕ−ｔ−４Ｅｔ ＣＡ ＨＯＩｆ Ｃ１ｌ□
Ｃ６１１４０ＣＦ２ＣＨＰ２−４Ｐｒ ＣＩ ＩＩ
ＯＨＣＨｚ ＣｂｔｌａＣＯＯＰｅｎ−ｔ−４
Ｐｒ Ｃｌ２ ＨＯＩＩ ＣＨｚ Ｃ６１１４
−（Ｃ７−Ｐｒ−ｉ−２）−４！’ｒ−ｉ ＣＩ
ＨＯＩｔ ＣＨｚ Ｃ６Ｈ４−（Ｃ３−ＣＮ−１）
−４Ｐｒ−ｉ ＣＩ ＩＩ ＯＩｆ Ｃ１
１ｚ Ｃｄ１４ＳＣＦｚＣＦｚＣＦ３−４Ｐｒ−ｉ
Ｃｆ Ｉｔ ＯＨＣ１１２Ｃ６１１４ＣＯＯ−
（Ｑ４）−４Ｂｕ Ｃｌ２ ＩＩ ＯＩｔ
Ｃｌ１２ Ｃ６１１ａＣＯＯＣＭｅｚＣ）Ｃ６１１ａ
ＣＯＯＣＣＩ ＨＯＩｆ Ｃ！！ｚ Ｃｄ４−（
Ｃ８−Ｐｒ−ｉ−２）−４Ｂｕ−ｉ ＣＩ Ｉｔ
ＯＨＣ１１２Ｃａ１１４ＣＯＯＢｕ−ｔ−４Ｂｕ
−ｉ ＣＩ ＩＩ ＯＨＣ１１ｚ ＣＪｎ
ＣＯＢｕ−ｔ−４ｎｕ−ｉ Ｃｆｆ１ ＨＯ！（
Ｃ１１ｚ ＣＪ４ＳｉＭｅ２−４Ｐｈ ＣＩ Ｉ
ｔ ＯＩｔ Ｃ１１２Ｃｄ４−（Ｑｌ−Ｃｆｚ−
２＋２−Ｍｅ−１）−４Ｐｈ ＣＩ ＨＯＩＩ
ＣＨ２ＣＪ１４ＣＯＮ（Ｐｒ−ｉ）ｚ−４Ｅｔ Ｃ１
；！ ＨＯＨＣ１１２ＣａＨ４Ｃ００Ｐｒ−ｉ−４Ｅ
ｔ Ｃｌ２ＨＯＩＩ ＣＩｌ□ Ｃ６１１４ＳＯＣ
ＨＦｚ−４Ｅｔ ＣＩ Ｉｔ ＯＨＣｌ１２
ＣＪ４ＣＯＮＭｅｚ−４Ｍｅ ＣＩ ＨＯ４−Ｆ
ＣＩＩｚ Ｃａ１ｌａＣＯ°ＯＰｒ−ｉ−４Ｍｅ
ＣＩ Ｉｔ ０ ４−Ｆ ＣＨｚ Ｃｄ４Ｓ
ＯＣＨｈ−４Ｍｅ ＣＩ ＨＯ４−Ｆ ＣＨ２Ｃ
６Ｈ４ＣＯＮＣ６Ｈ４Ｃ０Ｎ ＣＩ Ｈ０４−ＯＭ
ｅ Ｃｔｌｚ Ｃ６１１ＣＯＯＰｒ−ｉ−４Ｍｅ
Ｃ１ｌｌ ０４−ＯＭｅ ＣＨｚ Ｃ６１１ｎＣ
ＯＣ６１１ｎＣＯＮ Ｂｒ Ｉｔ ＯＨＣｔ
ｌｚ ’Ｃ，ＩＩｌＩｎＣ００Ｐｒ−ｉ−４ Ｂｒ
ＨＯＩＩ ＣＨ２ＣａＨ４Ｈ４Ｓ０ＣＨＦ２−４
ＯＭｅ ＩＩ ＯＩＩ Ｃ１１ｚ Ｃｉ
、ＩＩｓＣＯＯＰｒ−ｉ−４Ｍｅ ＯＭｅ ＩＩ
ＯＩＩ ＣＨｚ ＣｂＨａＣＯＮＭｅｚ−４Ｍ
ｅ ＯＭｅ ＩＩ Ｏ！（ＣｌＩ２ Ｃ６Ｃ
６Ｈ４５ＯＣＩＩＦ２−４ ＯＭｅ Ｉｔ ０
４−Ｆ ＣＨｚ Ｃ６Ｃ６Ｈ４Ｃ００Ｐｒ−ｉ−４
Ｆ Ｉｔ ＯＩＩ ＣＨｚ Ｃａｌ１４ＣＯ
ＯＢｕ−ｔ−４Ｍｅ Ｆ Ｉｆ ＯＨＣＨｚ
Ｃｄ４−（Ｃ３−ＣＮ−１）−４Ｍｅ Ｆ Ｉ
Ｉ ＯＩＩ ＣＴｏ Ｃ６Ｃ６１１４０ＣＦｚ
ＣＩＩＦｚ−４Ｂｒ ｔ（ＯＩＩ Ｃ１１ｚ
Ｃｄ４ＣＯＯＰｅｎ−ｔ−４Ｍｅ Ｂｒ ＨＯＨ
ＣＬ ＣＪＩ４Ｂｕ−ｔ−４Ｍｅ Ｂｒ
ＨＯＩＩ ＣＨ２Ｃ６Ｈ４Ｃ００−（口４）−４
Ｍｅ Ｂｒ ＨＯＨＣＨ２Ｃｄ１４ＳＣＦｚＣＦ
ｚＣＦ３−４Ｍｅ Ｂｒ ＨＯ１１ＣＨＣ６Ｈ４−
（Ｃ７−Ｐｒ−ｉ−２）−４ＲＲ’ Ｒ” Ｘ
Ｙ１％Ａ ＱＭｅ Ｉ ＩＩ
ＯＩｆ Ｃｌ１ｚ ＣｂｌｌｎＳｉＭｅｚ−
４Ｍｅ ＯＭｅ Ｉｔ ＯＩｔ Ｃｔｌｚ
ＣｓＣ５１１４ＣＯＯＢｕ−ｔ−４ＯＭｅ Ｉｆ
Ｏｔｌ Ｃｔｌｚ Ｃ６１１４ＣＯＯ（Ｃ
６１１４ＣＯＯ（Ｑ４− ＯＭｅ Ｉｆ ＯＩ
Ｉ Ｃ１１ｚ ＣｂＨＪｕ−ｔ−４Ｍｅ ＯＭ
ｅ Ｉｆ ＯＩＩ ＣｌＩ２ Ｃ６Ｃ６１
１４−（Ｃ３−ＣＮ−１）−４ＯＭｅ Ｉｆ Ｏ
ＨＣＨｚ ｃ６ｎ４ｓｉＭｅ３−４Ｍｅ ＯＭｅ
ＩＩ ＯＨＣ１１ｚ Ｃｂｔ１４０ＣＰｚＣＨ
Ｆｚ−４Ｍｅ ＯＭｅ ｔｌ ＯＨＣＨｚ
ＣＪＩ４ＣＯＮ（Ｐｒ−ｉ）ｚ−４Ｍｅ ＯＭｅ
ＩＩ ＯＨＣｌｌ□Ｃ６Ｃ６１１４ＣＯＢｕ４−４
ＯＭｅ ＨＯＨＣＨｚ Ｃ６Ｈ４−（Ｃ８−Ｐ
ｒ−ｉ−２）−４Ｍｅ Ｏ［ｉｔ Ｉｔ ＯＨ
Ｃｌ１ｚ ＣＪ１４ＣＯＯＰｅｎ−ｔ−４Ｍｅ Ｏ
Ｅｔ ＩＩ ＯＨＣ１１ｚ Ｃｄ４ＳＣＦｚＣ
Ｆ２ＣＦｉ−４Ｍｅ ＯＥｔ ＩＩ ＯＨＣｌ
１ｚ ＣＪｌａ−（Ｃ７−Ｐｒ−ｉ−２）−４Ｍｅ
ＯＥｔ ＨＯＨＣ１１２Ｃ６１１４ＣＯＯ−（
口４）−４Ｍｅ ０Ｐｒ−ｉ ＩＩ ＯＨＣ１１
２ＣＪＩａＣＯＯＣＭｅｚＣＨｚＣｆ−４Ｍｅ ０Ｐｒ
−ｉ ＨＯＨＣ１（ｚ Ｃ６１１＜−（Ｑｌ−Ｃｊ
！ｚ−２，２−Ｍｅ−１）−４Ｍｅ ＣＮ ＨＯ
ＨＣｌ１ｚ Ｃ６Ｃ６１１ｎＣＯＯＢｕ−ｔ−４ＣＮ
ＩＩ ＯＨＣＨｚ Ｃｄ４０ＣＦｚＣＩＩ
Ｆｚ−４Ｍｅ ＣＮ ｔｌ ＯＨＣ１１ｚ
ＣＪＩＪｕ−ｔ−４ＲＲ’ Ｒ” Ｘ Ｙ
、 Ａ ＱＭｅ ＮＯｚ ＨＯｆｌ
ＣＨｚ Ｃ６Ｃ６Ｈ４Ｃ０Ｏ−（Ｑ４）−４Ｎ
ｏｚ ＨＯＨＣ１ｈ Ｃｄ４−（Ｃ７−Ｐｒ−ｉ−２
）−４Ｍｅ Ｃｆ Ｍｅ ＯＩｔ Ｃ１１
ｚ Ｃ６Ｃ６１１４ＣＯＯＢｕ−ｔ ＣＩ Ｍｅ
ＯＨＣＨ２Ｃ６Ｃ６Ｈ４Ｃ０Ｏ−（Ｑ４）−４Ｃｊ
！ Ｍｅ ＯＨＣＨ２Ｃｂ）Ｉ４ＣＯＯＢｕ−ｔ−
４Ｍｅ Ｃｊｌ： Ｍｅ Ｏｔｌ ＣＨ２Ｃ
６Ｃ６Ｈ４０ＣＦ２ＣＨＦ２−４ ＣＩ Ｍｅ
ＯＩｆ ＣＨｚ ＣｂＨａＣＯＢｕ−ｔ−４Ｍｅ
ＣＩ Ｍｅ ＯＨＣＨ２Ｃ６Ｈ４−（Ｃ７−Ｐ
ｒ−ｉ−２）−４Ｍｅ Ｃｌ２ Ｅｔ ＯＩＩ
ＣＨｚ ＣＪＩｎＣＯＯＰｅｎ−ｔ−４Ｍｅ
ＣＩ Ｅｔ ＯＨＣｆｈ Ｃ６Ｃ６１１４ＳＣＦ
ｚＣＦｚＣＦ３−４ ＣＩ Ｅｔ ＯＨＣ１１ｚ
Ｃ６Ｃ６１１４ＣＯＮ（Ｐｒ−ｉ）ｚ−４ＣＩ
Ｐｒ ＯＨＣＨｚ ＣＪｎＣＯＯＣＭｅｚＣＨＬＣ
／！−４Ｍｅ ＣＩ Ｐｒ ＯＨＣ１ｌ□ｃ＆Ｉ
Ｉ４ｓｔＭｅ、４Ｍｅ ＣＩ Ｐｒ ＯＨＣ１１
ｚ Ｃ６Ｈｎ−（ＱＢ−Ｐｒ−ｉ−２）−４Ｍｅ
ＣＩ Ｐｒ−１０ＨＣＨｚ Ｃ６１１ｎＣＯＯ−Ｃ
６１１ｎＣＯＯ−（Ｑ４− ＣＩ Ｐｒ−１０ＨＣ
Ｈｚ ＣＪＬ−（Ｃ３−ＣＮ−１）−４Ｍｅ ＣＩ
Ｂｕ Ｏ１１ＣＴｏ ＣａＣａｌｌｎＣ００Ｂ
ｕ−ｔ ＣＩ Ｂｕ ＯＩｔ ＣＨｚ Ｃ
６１１４−（Ｑｌ−Ｃｊ！ｚ−２，２−Ｍｅ−１）−４
Ｍｅ ＣＩ Ｍｅ ＯＨＣＨｚ Ｃａｔｌ、Ｃ
ＯＯＰｒ−ｉ−４ＲＲ’ Ｒ２Ｘ Ｙ、
Ａ ＱＭｅ ｃｇ Ｍｅ ＯＩｔ
Ｃｌ１２ Ｃｂｌ１４ＣＯＮＭｅ２−４Ｍｅ
ＣＩ２ Ｍｅ ＯＩＩ ＣｌＩ２ Ｃ６Ｃ６
１１４ＳＯＣｔｌＦｚ−４（、ｐ、Ｍｅ Ｏ４−Ｆ
Ｃｌ１ｚ Ｃ６ｔ１４ＣＯＯＰｒ−ｉ−４Ｍｅ
ｃｐ ＩＩ Ｓ ＨＣｌＩ２ Ｃ，１１４
ＣＯＯＢｕ−ｔ−４Ｍｅ ＣＡ ＩＩ
Ｓ ＨＣＩＩＺ Ｇ６１１４ＣＯＯ−（口４
）−４Ｍｅ ＣＩ２ １１ Ｓ ＨＣ１１ｚ
ＣＪｔＣＯＯＣＭｅｚＣ１ｌｚＣＩ！、−４Ｍｅ
ｃｘ ＨＳ ＩＩ Ｃ１１ｚ Ｃａｔ（
Ｊｕ−ｔ−４Ｍｅ ｃｐ Ｉｔ Ｓ Ｉｔ
Ｃ１１ｚ Ｃ６Ｈ４−（Ｃ３−ＣＮ−１）−４
Ｍｅ ｃｐ ｔｌ Ｓ ＨＣ１１ｚ
Ｃ６１１ａＳｉＣ６１１ａＳｉ ｃｐ Ｉｔ
Ｓ ＨＣＩＩＺ Ｃ６Ｃ６１１４０ＣＦ２ＣＨＦ
２−４ Ｃｆ ＨＳ Ｉｔ Ｃｌ１ｚ
ＣｂｌｌｎＳＣＦｚＣＦｚＣｈ−４Ｍｅ Ｃｆｆ
ｔｌ Ｓ ＩＩ Ｃ１１ｚ ＣＪＩ４Ｃ
ＯＮ（Ｐｒ−ｉ）ｚ−４ＦＩｅ ＣＥ Ｉｔ
Ｓ ）ｌ ＣＩＬｚ ＣｂｌＬｓＣＱＢｕ−
ｔ−４Ｍｅ ＣＩ２ Ｉｔ Ｓ ｔｌ
Ｃｌ１ｚ Ｃ６Ｃ６ｌ１ａ−（Ｃ８−Ｐｒ−ｉ−２
）−４（Ｊ ｔｌ Ｓ Ｉｔ Ｃｌ１２
Ｃ６１１４（：ＯＯＰｒ−４−４Ｍｅ ＣＩ２
ｔｌ Ｓ Ｉｆ ＣＨｚ Ｃ６Ｉ１４
ＣＯＣ６ｌ１４ＣＯＮ ＣＩ Ｉｔ Ｓ
ＩＩ Ｃ１１ｚ ＣｂＨ，ＳＯＣＩＩＦｚ−４Ｍ
ｅ ＣＩ ＨＳ ４−Ｆ ＣｌＩ２ Ｃ６Ｃ
６Ｈ４Ｃ００Ｂｕ４−４ Ｃｊ！ Ｉｔ Ｓ
４−Ｆ Ｃｌ１ｚ Ｃ６１１４ＣＯＯＰｒ−ｉ−
４ＲＲ’ Ｒ” Ｘ ＹｆｆｉＡ
ＱＭｅ Ｃ１，Ｉｔ Ｓ ４−Ｐ ＣＨｚ
Ｃ６Ｃ６１ＩａＢｕ−ｔ−４Ｃ１ｔｌ Ｓ
４−Ｐ ＣｌＩ２ ＣＪｎＳｉＭｅｚ−４Ｍｅ
ＣＩ２ ＨＳ ４−Ｆ Ｃｌ１２ Ｃ６ＨＪＣ
ＦｚＣｔｌＦｚ−４Ｍｅ ＯＭｅ ＨＳ ＨＣｌ
１２ Ｃ６Ｃ６Ｈ４Ｃ０Ｏ−（Ｃ４）−４ＯＭｅ
ＨＳ ｔｌ Ｃｌ１ｚ ＣＪｎＣＯＯＣＭｅｚＣ
ＨｚＣＮ−４Ｍｅ ＯＭｅ Ｉｔ Ｓ ＩＩ
Ｃ１１２ＣＩ、ｌＩ４ｓｃＦＺｃＦ２ｃＦ３−４Ｍｅ
ＯＭｅ ＩＩ Ｓ ＨＣ１１ｚ ＣＪ４Ｃ
ＯＯＰｒ−ｉ−４Ｍｅ ＯＭｅ ＩＩ Ｓ Ｈ
ＣＨｚ Ｃ６Ｈ４ＣＯＮＣ６Ｈ４Ｃ０Ｎ Ｂｒ
ＨＳ ＨＣＨ２Ｃ６１１＜ＳｉＭｅ：＋−４Ｍｅ
Ｂｒ ＨＳ ＨＣＨｚ ＣＪ４ＣＯＯＰｒ−４−
４Ｅｔ ＣＩ ＨＳ ＨＣ１１ｚ Ｃ６Ｈｎ
ＣＯＯＢｕ−ｔ−４Ｅｔ ＣＩ ＨＳ ＩＩ
ＣＨＣＨ２Ｃ６Ｈ４Ｃ００Ｐｒ−ｉ−４ＣＩ Ｍｅ
Ｓ ｔ（Ｃｔｌｚ Ｃ６ＨｎＣＯＯＢｕ−ｔ−４
Ｍｅ Ｃｆ Ｍｅ Ｓ Ｉｆ ＣＨｚ Ｃ
６１１４ＣＯＣ６１１４ＣＯＮ ＣＩ ＨＯ２−Ｆ
ＣＨｚ Ｃ６ＨｎＣＯＯＢｕ−ｔ−４Ｍｅ ｃ
ｚ ＋１ ０ ３−Ｆ ｃＨ，Ｃ１Ｃ１Ｈ４Ｃ０Ｏ
−（Ｃ４）−４ＣＩ Ｉｔ ０ ４−Ｆ ＣＨ２
ＣａＣａＨ４Ｃ００Ｂｕ−ｔ−４Ｃ！！、ｌｌ ０
４−Ｆ ＣＬ Ｃ，、ＬＣＯＯ−（Ｃ４−Ｍｅ−１
）−４Ｍｅ Ｃ１ｔｌ ０ ４−Ｆ Ｃ１１２Ｃ
６１１ａＣＯＯＣＭｅｚＣ６１１ａＣＯＯＣＲ’
Ｒ２Ｘ ＹＩＩＡ ＱＭｅ Ｃｆｆ
ＩＩ ０ ４−Ｆ Ｃｔｌｚ Ｃ６ＨＪｕ
−ｔ−４腕 ＣＩ２ ＩＩ ０ ４−Ｆ Ｃ
１１ｚ Ｃ６ＨＪ−（Ｃ３−ＣＮ−１）−４Ｍｅ
Ｃｆ２ ＩＩ Ｏ４−Ｆ ＣｌＩ２ Ｃ６
１１４ＳｉＣ６１１４Ｓｉ ｃｐ Ｈ０４−Ｆ
Ｃｌ１ｚ ＣＪＩ４０ＣＦｚＣＨＦｚ−４Ｍｅ
Ｃ１！Ｉ ０ ４−Ｆ Ｃ１１ｚ Ｃ６１１４
ＳＣＦｚＣＦｚＣＦ：ｔ−４Ｍｅ ＣＩ ＩＩ
０ ４−Ｆ Ｃ１１ｚ ＣＪ４ＣＯＮ（Ｐｒ−ｉ
）ｚ−４Ｍｅ ｃｐ ｔｌ ０ ４−Ｆ
Ｃ１１ｚ Ｃ６Ｃ６１１４ＣＯＢｕ−ｔ−４ＣＩ
Ｉｆ ０ ４−Ｆ ＣｌＩ２ ＣＪｎ−（Ｃ
７−Ｐｒ−ｉ−２）−４Ｍｅ Ｃ１ｔｌ ０４−
Ｃｌ Ｃ１１ｚ Ｃ６１４ＣＯＯＰｒｎ−ｔ−４Ｍ
ｅ ＣＩ Ｉｔ ０４−Ｃｌ Ｃ１１ｚ
Ｃ６１１４ＣＯＯＣＭｅｚＣＣ６１１４ＣＯＯＣＣｆ
ＩＩ ０４−Ｃｌ ＣＨ２Ｃ，１１，０Ｃ
ＩＩ□ＣＦ３−４Ｍｅ ＣＩ Ｉｔ ０４−
Ｃｌ ＣＨｚ ＣＪ４ＳＯＣＦｚＣＦｚＣｈ−４Ｍ
ｅ ＣＩ Ｈ０４−Ｃｌ Ｃ１１ｚ Ｃ６１１
４−（Ｑｌ−Ｃｊ２ｚ−２＋２−Ｍｅ−ＩＬ４Ｍｅ
ＣＩ Ｈ０４−Ｃｌ Ｃ１１ｚ ＣＪＬ−
（口８−８−Ｐｒ−３−２）−４ＣＩ ＩＩ
０４−Ｂｒ ＣＨｚ ＣＪＩａＣＯＯＢｕ−ｔ−４
Ｍｅ ＣＩ Ｉｆ ０４−Ｂｒ Ｃ１ｈ
Ｃ６１（４０ＣＦ２ＣＨＦ、−４Ｍｅ ＣＩ
ＩＩ ０４−Ｍｅ Ｃｌ１ｚ ＣＪ４ＣＯＯＰ
ｅｎ−ｔ−４Ｍｅ ｃｐ １１ ０４−Ｍｅ
ＣＨｚ Ｃ６１１４ＳｉＣ６１１４Ｓｉ ＣＩ
ＨＯ４Ｊｒ−ｉ ＣｌＩ２ ＣＪＩ４ＣＯＯ−（Ｃ４
−Ｍｅ−１）−４ＲＲ’ Ｒ２Ｘ ＹＩＩＡ口
ＭｅＣｊ２ ＨＯ４−Ｐｒ−１ＣＨ２ＣＪａ−（Ｃ３
−ＣＮ−１）−４ＭｅＣｊ２ ＨＯ４−ＯＭｅ
ＣＨｚ ＣＪａＣＯＯＢｕ−ｔ−４ＭｅＣ！！、）ｌ
０ ４−ＯＭｅ ＣＨｚ ＣＪ４ＣＯＯ−（
Ｃ４−Ｍｅ−１）−４ＭｅＣＡ １１ ０ ４−ＯＭ
ｅ Ｃ）１２ Ｃ６Ｈ４Ｂｕ−ｔ−４ＭｅＣｆ
ＨＯ４−ＯＭｅ Ｃｌ１ｚ ＣＪ４０ＣＦｚＣ
ｆｌＦｚ−４ＭｅＣ！！、ＨＯ４−ＯＭｅ ＣＨｚ
Ｃ６８４Ｃ６８４ＣＯＮ（Ｐｒ−４）ｚ−４！
Ｈ０４−ＯＥｔ Ｃ１１ｚ Ｃ，Ｈ，ＣＯＯＣ０
０Ｂｕ−ｔ−４／！ Ｉｔ Ｏ４−ＯＥｔ Ｃ
Ｔｏ Ｃ６Ｈ，ＳＣＦ２ＣＦ２ＣＦ３−４ＭｅＣｆｆ
ｉ ＨＯ４−３Ｍｅ ＣＨ２Ｃ６１Ｃ６１Ｉ４Ｃ
ＯＯＢｕ−ｔ−４，ｅ ＨＯ４−４−５Ｏｚ ｃｔ
ｔｚＣｂｌｌａＣＯＯＢｕ−ｔ−４ＭｅＣｊ２ ）１
０ ３−ＮＭｅｚ Ｃ１１□Ｃ，Ｉ１４ＣＯＯＢ
ｕ−ｔ−４Ｍｅ（／！ ＨＯ３−Ｅｔ ＣＨｚ
Ｃａｌ１４ＣＯＯＢｕ−ｔ−４ＭｅＣｊｌ！ Ｈ
０４−Ｂｕ−ｔ Ｃ１１ｚ Ｃ６１１Ｃ６１１ａ
ＣＯＯＢｕ−ｔ−４！、ＨＯ４−ＣＯｏＥｔ ＣＨｚ
ＣＪ４ＣＯＯＢｕ−ｔ−４Ｍｅ ＣＩ Ｉｔ
Ｏ２，４−Ｃ２□Ｃ１１２ＣＣ１１２Ｃ６１１４ＣＯＯ
Ｂｕ−ｔ−４ＨＯ３−ＣＦ’＋ ＣＨｚ Ｃ６Ｈ
ｎＣＯＯＢｕ−ｔ−４Ｍｅ ＣＩ ＨＯ３，４−ＯＣ
ＨｚＯ−ＣｌＩ２ ＣＪ４ＣＯＯＢｕ−ｔ−４ＲＲ’
Ｒ２ＸＹｍＡ ＱＭｅＣｆｆｉ
Ｉｔ ＯＩＩ −ＣＩＩＭｅ−ＣＪ（４ｃＯＯＢ
ｕ−ｔＭｅ（、ｅ ＩＩ ＯＩＩ −Ｃ１１２Ｃ
１１２ＣＩ＋２− Ｃ６Ｈ４ＣＣ６Ｈ４Ｃ００Ｂｕ−
ｔ Ｉｆ ＯＩＩ −ＣＩｌｚＣ１ｌ＝Ｃｌｌ−
ＣａｌｌａＣＯＯＢｕ−ｔＭｅＣ，ｅ ＩＩ ＯＨ
−ＣＩＩｚＣＭｅ＝ＣＩＩ−Ｃ，、ＩＩ４ＣｌＩ４Ｃ０
０Ｂｕ−ｔ ＩＩ ＯＩＩ −ＣＩＩＭｅＣＨ＝
ＣＩＩ−Ｃ６ＩＩ４Ｃ６ｌｌ４ＣＯＯＢｕ−ｔ ＩＩ
ＯＩＩ −ＣＩＩｚＣＩｌｚＯ−Ｃ６１１４ＣＣ
６１１４ＣＯＯＢｕ−ｔ ＩＩ ＯＩｔ −ＣＨ
ＭｅＣＩＩｚＯ−Ｃ，、Ｉｔ４ＣＯＯＢｕ−ｔＭａＣｆ
ＩＩ Ｏｔｌ −ＣＩＩＥｔ−Ｃ６＋１４ＣＯ
ＯＢｕ−を門ｅ Ｃｆｆ Ｉｔ ＯＩＩ −ＣＩ
ｌｚＣＩＩＭｅＣＩＩｚ−Ｃ，、ＩＩ４ＣＯｌＩ４Ｃ０
０Ｂｕ−ｔ ＩＩ ＯＩｔ −ＣＨＭｅ−Ｃ６＋
１４ＣＯＯ−（Ｃ４）−４ＭｅＣｆｆ ＩＩ ＯＩ
ｆ −ＣＩＩＭｅ−Ｃ６ＨＪｕ−ｔ−４ＭｅＣｆｆｉ
Ｉｔ ＯＩｔ −ＣｌｌＭｅ−Ｃ６１１ｎＳｉ
ＭｅＣ６１１ｎＳｉ Ｉｆ Ｏｔｌ −ＣＩＩＭ
ｅ−Ｃ６１１４０Ｃ６１１４０ＣＦＺＣＩＩＦ２−４
Ｉｔ ＯＨ−ＣＨＭｅ−Ｃ６１＋４ＳＣＦ２ＣＦＺ
ＣＦ３−４ＭｅＣｊ２ ＋１ ０ １１ −ＣｔｌＭ
ｅ−Ｃ６１ＬＣ６１Ｌ（Ｃ６１１４−ＣＪ２−４）−４
ＩＩ ＯＨ−ＣＨｚＣ１ｌ＝ＣＩ（−Ｃ６＋１４ＣＯ
ＯＰｅｎ−ｔ−４ＭｅＣｆ ＩＩ ＯＩｆ −Ｃ
ＩＩｚＣＩｌ＝ＣＩＩ−Ｃ６＋１４−（Ｃ３−ＣＮ−１
）−４ＭｅＣｆｆ Ｉｆ ＯＩＩ −ＣＩｌｚＣ
Ｍｅ＝ＣＨ−ＣＪＩ４ＣＯＯＣＭｅｚＣＨｚＣｊ２−４
門ｅｃｌ ＨＯＩｔ −ＣＩＩｚＣＭｅ＝ＣＩＩ−
Ｃ６１１ｔＣＬ−２＋４ＲＲ’ Ｒ２ＸＹｍ
Ａ ＱＭｅＣｆｆ ＨＯ
Ｉｆ −ＣＨｚＣＭｅ＝Ｃｔｌ−Ｃ６１１４Ｃ６１１
４０Ｐｒ−４ＨＯＨ−ＣＩＩｚＣＨｚＯ−ＣＪ４ＣＯＯ
−（Ｃ４−Ｍｅ−１）−４ＭｅＣＡ ＩＩ ＯＩｔ
−ＣＩｌｚＣＨｚＯ−Ｃ６１ＩｓＣＣ６１ＩｓＣＯ
Ｂｕ−ｔ−４ｌ ＯＩＩ −ＣＨｚＣＩｌｚＯ−Ｃ
Ｊ１４Ｍｅｚ−２＋６−ＯＰｈ−４ＦＩｅＣＩ ＩＩ
Ｏｔｌ −ＣＨ２Ｃ１＋２０− Ｃ６１１４
Ｃ６１ｌ４．６−ＣＨ６−Ｃ０Ｐｈ−４ＨＯＨ−ＣＩＩ
ｚＣＨｚＯ−Ｃ６Ｉ（４Ｍｅｚ−２，６−Ｃｆｆ６−Ｃ
ｌ１ｚＰｈ−４ｌ！ ＯＩＩ −ＣＨ２Ｃ１＋２０
− Ｃ６１１４Ｃ６１ｌ４．６−６−０（Ｃ６１１
４−Ｃ４−４）−４ＣＩ Ｍｅ Ｏ４−Ｆ −Ｃ
Ｈｚ−Ｃ６Ｃ６１１ｎＣＯＯＢＬＩ−ｊ−４Ｂｒ
Ｈ０４−Ｆ −ＣＨ２−Ｃ６Ｃ６１１４ＣＯＯＢｕ
−ｔ−４ＣＩ Ｉｔ ０４−Ｆ −ＣＨＭｅ−
ＣＪ４ＣＯＯＢｕ−ｔ−４Ｍｅ ＣＩ ＩＩ ０４
−ＯＭｅ −ＣＨＭｅ−Ｃｉ、Ｈ４Ｈ４Ｃ００Ｂｕ−ｔ
−４ＣＩ ＨＳ ４−ＯＭｅ −ＣＨｚ−ＣＪ１４Ｃ
ＯＯＢｕ−ｔ−４Ｍｅ ＣＩ Ｅｔ Ｓ ４−ＯＭｅ
−ＣＨｚ−Ｃ，ｌＩａＣＯＯＢｕ−ｔ−４Ｍｅ Ｆ
ＩＩ ０４−（／２ −Ｃｌｌｚ−Ｃ６１１ｎ
ＣＯＯＢｕ−ｔ−４Ｅｔ ＣＥ ｔｌ ０４−Ｃｊ
！ −ＣＨｚ−Ｃ６ＩＩ４ＣＯＯＢｕ−ｔ−４Ｅｔ
ＣＪ２ ＨＯ４−ＯＭｅ −ＣＨｚ−ＣＪ４ＣＯＯＢ
ｕ−ｔ−４Ｍｅ ＯＭｅ ＩＩ Ｏ４−ＯＭｅ −
ＣＨｚ−ＣＪ１４ＣＯＯＢｕ−ｔ−４Ｍｅ ＯＭｅ
Ｈ０４−Ｆ −ＣＩＩＺ−ＣＪ（ａｃＯＯＢｕ−ｔ
−４ＭｅＯＥｔ ＨＯＨ−Ｃ１ｌｚＣＩＩ’Ｃｌ１−
ＣＪＩ４ＣＯＯＢｕ−ｔ−４ＲＲ’ Ｒ
２ＸＹ、Ａ ＱＰｒ ＣＩ
Ｍｅ Ｏ４１−ＣＨｚ−Ｃ６１１４ＣＯＯＢｕ−ｔ−４
Ｐｈ ＣＪ２ ＩＩ ０４−Ｆ −Ｃ１
ｌｚ−Ｃ６１１ａＣＯＣ６１１ａＣＯＯＢｕ−ｔ−４Ｉ
Ｉ ＯＨＣｌ１２ ＣＪｌｎＣＯＯＢｕ−ｔ−４
ＭｅＣＯＯＭｅ ＩＩ ＯＩＩ
Ｃｌ１２ Ｃ６１１４ＣＯＯ−（口４−Ｍｅ−
１）−４ＭｅＣＯＯＭｅ Ｉｔ ＯＩｔ Ｃ
ｌ１ｚ Ｃａｌ１４Ｂｕ４−４ＭｅＣＯＯＭｅ
ｔｌ ＯＨＣＨｚ ＣＪ１４０ＣＦｚＣｔ（Ｆ
ｚ−４ＭｅＣＯＯＭｅ ＩＩ Ｏｔｌ Ｃ１
１ｚ Ｃ６Ｃ６１ＩｎＳｉ：＋−４ＭｅＣＯＯＥｔ
ＩＩ ＯＩｆ Ｃｌ１ｚ Ｃ６１１ａ
ＣＯＣ６１１ａＣＯＯＢｕ−ｔ−４Ｉｔ ＯＨＣＩＩ
Ｚ Ｃ６＋１４−（Ｃ３−ＣＮ−１）−４門ｅｃＯ
ＯＥｔ ｔｌ ＯＩＩ Ｃｌ１ｚ
ＣＪＩ４ＳＣＰｚＣＦ２ＣＰ３−４ＭｅＣＯ
ＯＩＥｔ ＩＩ ＯＩｔ Ｃｌ１２ Ｃ
６１１ｎＣＯＣ６１１ｎＣＯＮ（Ｐｒ−ｉ）ｚ−４ＨＯ
ＩＩ ＣｌＩ２ Ｃ６１４ＣＯＯｕ−ｔＭｅＣ
ＯＯＰｒ−ｉ Ｉｔ Ｏｔｌ Ｃｔｈ Ｃ
６ＩＩｘＣＯＯＢｕ−ｔ−４ＭｅＣＯＯＰｒ−ｉ Ｈ
ＯＨＣＨ２ＣＪ４ＣＯＯ−（Ｃ４）−４ＭｅＣＯＯＢｕ
−ｔ Ｉｆ ＯＩｔ Ｃ１１ｚ ＣＪＩａ
ＣＯＯＢｕ−ｔ−４ＭｅＣＯＯ１３ｕ−ｔ Ｉｆ
ＯＩｔ ＣＨｚ Ｃ６１１ａＯＣＦｚＣ６１１
ａＯＣＦｚＣＩＩＦｚ ＩＩ ＯＩｔ Ｃ１１
ｚ ｃ６１１４ｎｕ−ｔ−’ｉＭｅＣＯＯＢｕ
ＨＯＩＩ Ｃ１１ｚ ＣＪＩ４ＣＯＯＢｕ−
ｔ−４ＭｅＣＯＯＢｕ ＩＩ ＯＩｆ Ｃ
ｌ１２ Ｃ６Ｃ６ｌ１ｎＳｉ：＋上記の第１表の
Ｑ１〜Ｑ５７は次の構造式で表される基である。(Margins below) Table 1 Me CI in compound g! , It OII C11z P
hMe Cj! II OHC11z C6
H4F-4Me CI It OII C1
1z Cbl14Cj! -2Me cz II
OII CHz C,l+,CI! , -3Me
cz It OHClI2 CbHaCI
! -4Me CI II OIt C11z
CallJr-4Me CI II OI
I C11z Callal-4Me CI
Il OIf C1h C683P! -2,6
Me CI If OII C11z C
6113C12-2,4Me CI HOII
Cl12CbllzCl,z-3,4MeC/
! II OHCHz CbllJrz-3,
5Me CI HOHC11z C,)I:+F
-3, Cj! -4RR' R2X YIIA
QMec! ! , HOII C11
z CJnEt-3CHCi! , It OII
ClI2 CbHaPr-4Me CI
If OIt ClI2 c6114
pr-t-2CHCI If OHCHz
CJI4Pr-i-4Me CI It
OIt Cl1z CJJu-3CHCI
HOII Cl1z CJJu-4Me
CI2 II Oll Cl12 C
6C611nBu-i-4CI II OHC
IIZ C6C6114BII-5-4Cf
II OII Clh CJJu-t-2
CHCI II OII Clh C
6HJu-t-3CHCff It OII
C1h C6C611Ju-t-4Cjl:
II OHCHHz C6H4Pen-4M
e CIIZ tl OIf CII2
CJI4Pen-s-4Me Cff I
I OIt Cl1z CJI4Pen-
t-4Me C1II O! ! Cl1z
C6113C-e-3+But-4Me CI
It OII C11z C61I
,Me-3,But-4MeCfH
OIf Clh C6112M1322
．． 5. Pr-4Me CI2 HOHCHz
CbHa-CMezCN-4RR'R”X
YI, lA QMe CIIZ)
! OII C1(Z C6H4-(C2)
-4Me C1tl Otl CH2C&+(
4-(Q3-CN-1)-4Me Cf HOtl
ClI2 C6C6114-(Q4)-4CI
It OHCH2C6H4-(C5)-4Me
C4! II OII C11z C
1,84-(C6)-4Me CI HOHC1b
C6C6H4-813X-4CI II
OHCHz C6C611a-Ph-4ci! , I
I OHC82C, II, -(C6H4F-4)-
4Me CIIZ If Oll CH2C
6H4-(C,H4CI2-4)-4Me CI
II OII Cl12 C6H4-(C6
H4CF:l-1-4)-4CI It OIt
Cl12Ci, IL-CMezOMe-4M
e Cff HOHCl1z C6Qa-(CH
=CH-COBu-t)-4Me CI If
OHCHz C=)I4-(CII=Cll-C
OOEt)-4Me CI HOHCHz C
611n-(CI(=CBrz)-4FIe CI
HOHCHz CaH4-CMezCOOEt-
4Me CI HOHCHz C6C6H4C
00l1-4 CI It OII CHz
Cbll, COOMe-4Me CI It
OHCHz C6C6114COOEt-2
Ci! , It OIt Cl1z Ca1l
<C00Et-3RR' R”X YI, lA
QMe CI! , II Oit
CH, C6C6114COOEt-4CI2 HO
HCHz CJnCOOPr-4Me CI
II OHCtlz C6tlaCOOPr-
i-2CHCI II OHClI2 C6
11COOPr-i-3CHC1tl OII
ClI2 C6C611nCOOPr-i-4CI
HOtI Cl12 C6C611nCO
OBII-4CI2 II OHCL C
64COOBu-i-4Me CI2 HOHC1
1z C6tlaCOOBu-s-4Me CI
If OIf Cl12 C,, IIl
InCooBut-2(/2 It OHCH
z C6C6H4C00Bu-t-3CI HO
HCtlz Cal14COOBu-t-4Me
CI It OII C)lz CJn
COOPen-t-3CHCI It O11
C112Ci, IllnCooPen-t-4Cf
II OHC11z CaCallnC00
CHEtz-4Cj! It OIf CH2
C6C6114Coo(Q3)-4cz)I
OHC1h C, Il, COO(Q3-MeCoo
(Q3- CI It OII Ct(z
C614COOCMezCII=C6H4C00C
”, ffi HOII C11z C6C61
14COOIIex-4CI It OIt
C11□C611,COOCMezPr-C00CR'
R2X Yl, l 8
RoMe CI HOHC112C6114
CC6114COOCET2 Cj! HOHC
1(z CaH, COOCHMeBu-C00CH
C1It OHCtb C6114COO
-(mouth 4)-4Me C1! , HOtl Ctlz
C6H4COO-(C6H4C0O-(Q4-
CI HOHCl1z C611,COO-(
C00-(Q4-.6)-4Me CI HOHC
lI2 C6C6114COO-(C6)-4Cf
HOIt C112C6H4COOCtl(Pr
-i)z-4Me Cf HOIt ClI2
C611aCOOCET*-4Me CI
HOIt Cl1z C6H4C0OCIIMe
Ph-4Me CI HOIf Cl12
Ct, H4H4C00Czl140Ph-4CI
II OHClI2 C611nCC611
nCOOCzH40CI It OIt C
l12 CJ4COOCMezCIIzOMe-4
Me CI II OHCHHz C61
1COOCMezCOOMe-4Me CI HO
HCHz CJ4COOCHzCh-4Me C
I HOHC1b C6114COOC1l(C
F+)z-4Me CI HOHCH2CJnCO
OCII (C1lzCf)z-4Me CA I
I OHC1h C6114COOC6114
COOC, e-4Me Cl2 If OI
I CH2C64COOPh-4Me C1tl
OHCl1z C6114COO(C6IIn
Cjl! -4L4RR' R2X Yffi
A QMe CI2 II O
tl C11z C611:+Cj2-3. C.O.
C00Bu-t-4CE II OHCl1z
C611C6114CO5 gate e Cf I
t OIt Cl1z Ct, I14COS
Et-4Me CI If OIt Cl
h C6C6114COSPr-i-4Ci I
t OIt Cl12 C7114CO3B
u-t-4Me Ce It OIt C
11z C611nCC611nCONHCI
It OIt C11z CJI4CON
HPr-i-4Me CI2 It OII
C11z CbII<CONIIBu-t-4
Me CI2 II OHC11z C
6114COC6114CON Cf II
OII C11z CJ4CON(Pr-i)
z-4Me CI It O'It C1
1z C61LCONMC61LCON Cff
II OIt Cl1z C611n
CC611nCOC1HOIt Cl1z CJ
14COCOOEt-4Me CI2 11 0
II Cl1z C6C6114COCO
OPr-i-4Cf tl OIf Cl1
2 Cd14COPr-4Me CI HO
If C11z Cd14COPr-i-4Me
C/2 tl OII Cl1z
C6HnCOBu-t-3Me CI II O
It CHHz C6C6H4C0Bu-t-4C1
It OIt C11z C6114COC
C6114COCR' R2X Yffi A
QMe CN HOII Cl1
z CJ, COCMezCOOMe-4Me C
I HOII Chz Ci,! licOPh
-4Me C1110HCH2C6C6H4C0(C
6H4Cffi-4)-4CI HOHC112CJ
4CO(Cd14CFi-4)-4Me CI I
f OHC11z C4C4ll4CO (CJ
Ju-t-4)-4CI It OII Cl
1z C6 day Jez-2,6-6-C0Ph-4C
1110HC11z ChH4CO-(Q9)-4
Me CI It OHCH2C6C6114
CO-(QIO)-4CI HOIt Chz
C611nC611nCO-(QIO-,6)-4M
e C1110HCH2C6H4-(C7-M+3-
3-2)-4Cjl! HOHCHz CbII
4-(C7-Mez-2,4)-4Me Cjl!
It OHCl12C6C611n-(C
7-Et-2)-4CI II Ofl C1
1z C,II4-(Q8-Me-2)-4Me
CI It OHCH2C6C6114-(Q
8-CN-2)-4CI H011Ctlz C
611a-(Q8C611a-(Q8-COOCj!
II OHC11z Cj140Me-4M
e CI HOHCHz C6C61140E
t-4C1HOII Cl1z C6C6114
0Pr-4C1II OHC11z C611
40Pr-i-3RR'R2X'YLll A
QMe CI If ,O
II C11z C61140Pr-i-4 gate e
Cff1 HOII CH2C61140B
u-4 gate e CI II OII C11
z Cbll<OBu-i-4Me Cp, It
OIf C1,2C6H40BII-3-4M
e Cff1 Il OII Chz
C6C61140Bu-t-4cg II OI
I C11z C&+ (40CIIF2-3Me
CI2 II OIt ClI2 C
blaOCllh-4Me C1! , II O
If CHz C, H40CF:l-4Me
CI II OIt C112C61140
C112CF: l-4Me CI! , II OI
f CH2C6C61140CF2CIIFZ-3C
ff1 II OII ClI2 CJ
40CF2CHFz-4Me 112 II
OHC11z C6C611aOPen-4CI
If OII C11z C6C61
14011ex-4Cff It Ofl
Cl1z C611aO(04)-4th shift Cf
II OII CIl□ C6C61140
Ph-3CI! , II OIt Cl1z
C6C61140Ph-4C1110II C112
C611,0(C6H,Ci-4)-4Me CI
II OHCl12 Cd1nO(C,H
4CFz-4)-4Me cx II OI
I C11z C611z-(OCIlzO)-
3,4RR' R2X Y,% A
QMe CI II OHCHHz Cb
llJe-3+OPr-4Me CI If
OHCl1z CbII4-(OCIIzCIlzC
HzOMe)-4Me CI2 It
0 11 ClI2 C611,O-(口26-(,e-4,CFCF3-6)-4Cf HO
It CHz CbH40CHzPh-4Me
CI It OHCH2Cb)1.0CI(z(
Ci, II4-F-4)-4Me CI HOII
Ct(z CJ40Cl1MeCOOEt-4M
e Cf HOfl Cl1z C6HnCO
BueCOOBu-t-4Me Cf II
OIt CHz Cbl140CMezCOOEt
-4Me CI It OHCH2C6HnC
OBu-t-4Me CI It OHC) I
z C61(aOcO1(aOcOCI II
OHCl1z Cal14SMe-4Me (F
! HOHC11z C6H4SOC6H45OC
I If OIf CHz Cd14COP
r-4Me C1ll OHC11z CJI
4SEt-4Me CI If Otl C
l1z CJlaSPr-i-2Me C1It
OHC1C112CJ14SPr-i-3CI
HOII C11z C,, f14sPr-i-4
Me CI HOHCHz CblaaSOPr
-4-4Me CI HOHC11z Ci, I
I4SOzPr-i-4RR' I22 χ
YIIA QMe CI II
OHClI2 Ci, IIiSBu-t-4M
e CI II OII C112C6C
61145CIIFZ-3cp II Otl
C11z CbtlaSCHFz-4Me
CI II Otl CH2C6C6H45O
CIIF2-4 CI2 II OIt
C11z Cd14SO,CH['z-4Me
CI2 It OII Cl1z
C6C611nSCFzBr-4CI II O
It ClI2 Ci, II4schcIIF
z-4Me Cf2 It OII Cl
1z CbIlaSOCFzCHFz-4Me
CI II OHCIIZ C6+1
4SO2CF2CIIFZ-4Me C/2H
OI ClI2 C6C6114SC112C
F3-4 CI It OII ClI2
C6C6114SCF3-4 CI! ,If
OHCl12 C6C604CN-4CI
! , tl OHClI2 C6C6114N
O2-4cx It OIt Chz
CJI4SiMe+-4Me cx II
OII Cl1z CJlaCh-4Me
CI II OII Hz C6
HnCIIzCj2-4Me CI H011C1
h C6C611nCHzCIIzBr-4CI
If OHCtlz C17-COOB
u-t-5Me C1It O11Cl1z
C17-OCFzCIIh-5RR' R2X
YlllA QMe CI H
OHC1h C26-CA-4-CFi-6Me
C1t(OHCHHz C26-But-6Me
CI II OHCl1z C26-O
Pr-6Me CI2 HOHCH2C26-OC
FzCHFz-6Me ca It OHCH
z C26-I-6Me CI If
Ofl CHZ RO26-QC)1. (
C, H4H4F-4)-6CI It OII
CL C26-0(Ci, I14Ch-4)-6Me
CI It OII ClI2
B26-CO0Bu-L-6Me Cf
HOtl C1+2 023-Bu-5Me
C1l Ot(Ctlz (123-Br
-5Me CI HOII Ctlz (1
23-COOPr-i-5Me Cd2 II
Otl Cl1z C22-OPr-i-4M
e CI HOtl CHz C22-CO
OBu-t-5Me C1ll ON C)I
z C24-Me-5Me CI2 If
OHCH2G25-Mez-2+4Me CI
II OII Cl1z C27-Cf-6
Me CI HOHCHz 028Me C
1110HC112Q29 Me CI II OHCl1z C30
) I It' R2X YllllA
QMe CI If OIf
CIIZ Ro31Me CI II
OII CHz C32-Me-2Me C
1l (OII C112C33-CI2-5 old CI
II OHCH2'Q34-CF:l-2Me
CI2 It OHCtlz Q35M
e CI HOHC1h C36-Et-2M
e CQ If Ofl C11, C37-
Me-IMe CI! , tl OII Chz
C38-Me-IMe CI II O
II C11z C39-Me-IMe CI
It OHCHz C40-Mez-1,
3Me CI Hoff C112041-Me
-IMe CI HOHCHz C42-Me
-4Me CI HOit C11z Q4
3Me C1HOtl CHz Q44Me
C1tl OI Ctlz C45-Me-5
Me CP,)I OIt Cl1z C4
6-C1-6Me CI HOIf ClI2
C46-CF3-6 assistant CI2 HOHC1h
C47-CI2-7RR' R2X YmA
QMe CI II OII
Cl1z C49-Mez-2+4Me CI2
II OII C11z Q50Me
CI2 It OII Cl1z C
51-Me-5Me C! ! , HOHClI2
C52-Me-5Me CI It OII
Clh C53-Ph-1Me CI II
OIf C1b C54-Me-1,Bu
-t-3Me CI HOtl C112C55
-Mez-2+6Me CI II OIf
CHz Q56Me (,j! It
OHCHz Q57Me Cf2 If
OII ClI2 Cd4-(Qll)-4Me
CI HOHCH2C,Ha-(C12)-4M
e CI II OIt Clh C6
C6114-(C13)-4cz HOHCth
C6H4-(mouth 14)-4Me CI HO
If CIIZ C&+1. -(C15)-4M
e CI It OHCIIZ C&+1
4-(C16)-4Me CI II Ol(C
L CJaCL-(old 1)-4Me C1HOHC
lI2 C6C6114CHz-(C12)-4c
p HOHClI2 C6H4CHz-(C16
)-4Et CI HOit CL C,,
H4COOBu-t-4RR' R2X YI
IA QEt Cf II OI
I CIIZ C6114COO-C6114CO
O-(Q4- CI HOHCI(z CJJ
u-t-4Et CA HOIf C1l□
C61140CF2CHP2-4Pr CI II
OHCHz CbtlaCOOPen-t-4
Pr Cl2 HOII CHz C6114
-(C7-Pr-i-2)-4! 'r-i CI
HOIt CHz C6H4-(C3-CN-1)
-4Pr-i CI II OIf C1
1z Cd14SCFzCFzCF3-4Pr-i
Cf It OHC112C6114COO-
(Q4)-4Bu Cl2 II OIt
Cl12 C611aCOOCMezC)C611a
COOCCI HOIf C! ! z Cd4-(
C8-Pr-i-2)-4Bu-i CI It
OHC112Ca114COOBu-t-4Bu
-i CI II OHC11z CJn
COBu-t-4nu-i Cff1 HO! (
C11z CJ4SiMe2-4Ph CI I
t OIt C112Cd4-(Ql-Cfz-
2+2-Me-1)-4Ph CI HOII
CH2CJ14CON(Pr-i)z-4Et C1
;! HOHC112CaH4C00Pr-i-4E
t Cl2HOII CIl□ C6114SOC
HFz-4Et CI It OHCl12
CJ4CONMez-4Me CI HO4-F
CIIz Ca1laCO°OPr-i-4Me
CI It 0 4-F CHz Cd4S
OCHh-4Me CI HO4-F CH2C
6H4CONC6H4C0N CI H04-OM
e Ctlz C611COOPr-i-4Me
C1ll 04-OMe CHz C611nC
OC611nCON Br It OHCt
lz'C, IIlInC00Pr-i-4 Br
HOII CH2CaH4H4S0CHF2-4
OMe II OII C11z Ci
, IIsCOOPr-i-4Me OMe II
OII CHz CbHaCONMez-4M
e OMe II O! (ClI2 C6C
6H45OCIIF2-4 OMe It 0
4-F CHz C6C6H4C00Pr-i-4
F It OII CHz Cal14CO
OBu-t-4Me F If OHCHz
Cd4-(C3-CN-1)-4Me F I
I OII CTo C6C61140CFz
CIIFz-4Br t(OII C11z
Cd4COOPen-t-4Me Br HOH
CL CJI4But-4Me Br
HOII CH2C6H4C00-(mouth 4)-4
Me Br HOHCH2Cd14SCFzCF
zCF3-4Me Br HO11CHC6H4-
(C7-Pr-i-2)-4RR'R"X
Y1%A QMe I II
OIf Cl1z CbllnSiMez-
4Me OMe It OIt Ctlz
CsC5114COOBut-4OMeIf
Otl Ctlz C6114COO(C
6114COO(Q4-OMe If OI
I C11z CbHJu-t-4Me OM
e If OII ClI2 C6C61
14-(C3-CN-1)-4OMe If O
HCHz c6n4siMe3-4Me OMe
II OHC11z Cbt140CPzCH
Fz-4Me OMe tl OHCHz
CJI4CON(Pr-i)z-4Me OMe
II OHCll□C6C6114COBu4-4
OMe HOHCHz C6H4-(C8-P
r-i-2)-4Me O[it It OH
Cl1z CJ14COOPen-t-4Me O
Et II OHC11z Cd4SCFzC
F2CFi-4Me OEt II OHCl
1z CJla-(C7-Pr-i-2)-4Me
OEt HOHC112C6114COO-(
Mouth 4)-4Me 0Pr-i II OHC11
2CJIaCOOCMezCHzCf-4Me 0Pr
-i HOHC1(z C611<-(Ql-Cj
! z-2,2-Me-1)-4Me CN HO
HCl1z C6C611nCOOBu-t-4CN
II OHCHz Cd40CFzCII
Fz-4Me CN tl OHC11z
CJIJu-t-4RR' R” X Y
, A QMe NOz HOfl
CHz C6C6H4C0O-(Q4)-4N
oz HOHC1h Cd4-(C7-Pr-i-2
)-4Me Cf Me OIt C11
z C6C6114COOBut CI Me
OHCH2C6C6H4C0O-(Q4)-4Cj
! MeOHCH2Cb)I4COOBu-t-
4Me Cjl: Me Otl CH2C
6C6H40CF2CHF2-4 CI Me
OIf CHz CbHaCOBu-t-4Me
CI Me OHCH2C6H4-(C7-P
r-i-2)-4MeCl2EtOII
CHz CJInCOOPen-t-4Me
CI Et OHCfh C6C6114SCF
zCFzCF3-4 CI Et OHC11z
C6C6114CON(Pr-i)z-4CI
Pr OHCHHz CJnCOOCMezCHLC
/! -4Me CI Pr OHC1l□c&I
I4stMe, 4Me CI Pr OHC11
z C6Hn-(QB-Pr-i-2)-4Me
CI Pr-10HCHz C611nCOO-C
611nCOO-(Q4- CI Pr-10HC
Hz CJL-(C3-CN-1)-4Me CI
Bu O11CTo CaCallnC00B
u-t CI Bu OIt Chz C
6114-(Ql-Cj!z-2,2-Me-1)-4
Me CI Me OHCHz Catl, C
OOPr-i-4RR' R2X Y,
A QMe cg Me OIt
Cl12 Cbl14CONMe2-4Me
CI2 Me OII ClI2 C6C6
114SOCtlFz-4(,p,MeO4-F
Cl1z C6t14COOPr-i-4Me
cp II S HClI2 C, 114
COOBu-t-4Me CA II
S HCIIZ G6114COO- (mouth 4
)-4Me CI2 11S HC11z
CJtCOOCMezC1lzCI! , -4Me
cx HS II C11z Cat (
Ju-t-4Me cp It S It
C11z C6H4-(C3-CN-1)-4
Me cp tl S HC11z
C611aSiC611aSi cp It
S HCIIZ C6C61140CF2CHF
2-4 Cf HS It Cl1z
CbllnSCFzCFzCh-4Me Cff
tl S II C11z CJI4C
ON(Pr-i)z-4FIe CE It
S)l CILz CblLsCQBu-
t-4Me CI2 It S tl
Cl1z C6C6l1a-(C8-Pr-i-2
)-4(J tl S It Cl12
C6114(:OOPr-4-4Me CI2
tl S If Chz C6I14
COC6l14CON CI It S
II C11z CbH, SOCIIFz-4M
e CI HS 4-F ClI2 C6C
6H4C00Bu4-4 Cj! It S
4-F Cl1z C6114COOPr-i-
4RR' R”
QMe C1, It S 4-P Chz
C6C61IaBu-t-4C1tl S
4-PClI2CJnSiMez-4Me
CI2 HS 4-F Cl12 C6HJC
FzCtlFz-4Me OMe HS HCl
12 C6C6H4C0O-(C4)-4OMe
HS tl Cl1z CJnCOOCMezC
HzCN-4Me OMe It S II
C112CI, lI4scFZcF2cF3-4Me
OMe II S HC11z CJ4C
OOPr-i-4Me OMe II S H
CHz C6H4CONC6H4C0N Br
HS HCH2C611<SiMe:+-4Me
Br HS HCHz CJ4COOPr-4-
4Et CI HS HC11z C6Hn
COOBu-t-4Et CI HS II
CHCH2C6H4C00Pr-i-4CI Me
S t(Ctlz C6HnCOOBu-t-4
Me Cf Me S If Chz C
6114COC6114CON CI HO2-F
CHz C6HnCOOBu-t-4Me c
z +1 0 3-F cH, C1C1H4C0O
-(C4)-4CI It 0 4-F CH2
CaCaH4C00Bu-t-4C! ! ,ll 0
4-F CL C,, LCOO-(C4-Me-1
)-4Me C1tl 0 4-F C112C
611aCOOCMezC611aCOOCR'
R2X YIIA QMe Cff
II 0 4-F Ctlz C6HJu
-t-4 arm CI2 II 0 4-F C
11z C6HJ-(C3-CN-1)-4Me
Cf2 II O4-F ClI2 C6
114SiC6114Si cp H04-F
Cl1z CJI40CFzCHFz-4Me
C1! I 0 4-F C11z C6114
SCFzCFzCF:t-4Me CI II
0 4-F C11z CJ4CON(Pr-i
)z-4Me cp tl 0 4-F
C11z C6C6114COBu-t-4CI
If 0 4-F ClI2 CJn-(C
7-Pr-i-2)-4Me C1tl 04-
Cl C11z C614COOPrn-t-4M
e CI It 04-Cl C11z
C6114COOCMezCC6114COOCCf
II 04-Cl CH2C,11,0C
II□CF3-4Me CI It 04-
Cl Chz CJ4SOCFzCFzCh-4M
e CI H04-Cl C11z C611
4-(Ql-Cj2z-2+2-Me-IL4Me
CI H04-Cl C11z CJL-
(mouth 8-8-Pr-3-2)-4CI II
04-Br CHz CJIaCOOBu-t-4
Me CI If 04-Br C1h
C61 (40CF2CHF, -4Me CI
II 04-Me Cl1z CJ4COOP
en-t-4Me cp 11 04-Me
CHz C6114SiC6114Si CI
HO4Jr-i ClI2 CJI4COO-(C4
-Me-1)-4RR' R2X YIIA mouth MeCj2 HO4-Pr-1CH2CJa-(C3
-CN-1)-4MeCj2 HO4-OMe
CHz CJaCOOBu-t-4MeC! ! ,)l
0 4-OMe CHz CJ4COO-(
C4-Me-1)-4MeCA 11 0 4-OM
eC)12C6H4Bu-t-4MeCf
HO4-OMe Cl1z CJ40CFzC
flFz-4MeC! ! , HO4-OMe Hz
C684C684CON(Pr-4)z-4!
H04-OEt C11z C,H,COOC0
0Bu-t-4/! It O4-OEt C
To C6H, SCF2CF2CF3-4MeCff
i HO4-3Me CH2C61C61I4C
OOBu-t-4,e HO4-4-5Oz ct
tzCbllaCOOBu-t-4MeCj2)1
0 3-NMez C11□C, I14COOB
u-t-4Me(/! HO3-Et CHz
Cal14COOBu-t-4MeCjl! H
04-But C11z C611C611a
COOBu-t-4! , HO4-COoEt Hz
CJ4COOBu-t-4Me CI It
O2,4-C2□C112CC112C6114COO
But-t-4HO3-CF'+ CHz C6H
nCOOBu-t-4Me CI HO3,4-OC
HzO-ClI2 CJ4COOBu-t-4RR'
R2XYmA QMeCffi
It OII-CIIMe-CJ(4cOOB
u-tMe(,e II OII-C112C
112CI+2- C6H4CC6H4C00Bu-
t If OII -CIlzC1l=Cll-
CallaCOOBu-tMeC,e II OH
-CIIzCMe=CII-C,, II4ClI4C0
0But II OII −CIIMeCH=
CII-C6II4C6ll4COOBut II
OII-CIIzCIlzO-C6114CC
6114COOBu-t II OIt-CH
MeCIIzO-C,, It4COOBu-tMaCf
II Otl-CIIEt-C6+14CO
OBu-wo gatee Cff It OII-CI
lzCIIMeCIIz-C,, II4COlI4C0
0But II OIt -CHMe-C6+
14COO-(C4)-4MeCff II OI
f -CIIMe-C6HJu-t-4MeCffi
ItOIt-CllMe-C611nSi
MeC611nSi If Otl-CIIM
e-C61140C61140CFZCIIF2-4
It OH-CHMe-C61+4SCF2CFZ
CF3-4MeCj2 +1 0 11 -CtlM
e-C61LC61L (C6114-CJ2-4)-4
II OH-CHzC1l=CI(-C6+14CO
OPen-t-4MeCf II OIf-C
IIzCIl=CII-C6+14-(C3-CN-1
)-4MeCff If OII-CIlzC
Me=CH-CJI4COOCMezCHzCj2-4
Gate ecl HOIt -CIIzCMe=CII-
C611tCL-2+4RR' R2XYm
A QMeCff HO
If -CHzCMe=Ctl-C6114C611
40Pr-4HOH-CIIzCHzO-CJ4COO
-(C4-Me-1)-4MeCA II OIt
-CIlzCHzO-C61IsCC61IsCO
But-t-4l OII -CHzCIlzO-C
J14Mez-2+6-OPh-4FIeCI II
Otl -CH2C1+20- C6114
C61l4.6-CH6-C0Ph-4HOH-CII
zCHzO-C6I (4Mez-2,6-Cff6-C
l1zPh-4l! OII-CH2C1+20
- C6114C61l4.6-6-0 (C611
4-C4-4)-4CI Me O4-F -C
Hz-C6C611nCOOBLI-j-4Br
H04-F -CH2-C6C6114COOBu
-t-4CI It 04-F -CHMe-
CJ4COOBu-t-4Me CI II 04
-OMe -CHMe-Ci, H4H4C00But
-4CI HS 4-OMe -CHz-CJ14C
OOBu-t-4Me CI Et S 4-OMe
-CHz-C,lIaCOOBu-t-4Me F
II 04-(/2-Cllz-C611n
COOBu-t-4Et CE tl 04-Cj
! -CHz-C6II4COOBu-t-4Et
CJ2 HO4-OMe -CHz-CJ4COOB
u-t-4Me OMe II O4-OMe −
CHz-CJ14COOBu-t-4Me OMe
H04-F -CIIZ-CJ(acOOBu-t
-4MeOEt HOH-C1lzCII'Cl1-
CJI4COOBu-t-4RR' R
2XY, A QPr CI
Me O41-CHz-C6114COOBu-t-4
Ph CJ2 II 04-F -C1
lz-C611aCOC611aCOOBu-t-4I
IOHCl12 CJlnCOOBu-t-4
MeCOOMe II OII
Cl12 C6114COO-(mouth4-Me-
1)-4MeCOOMe It OIt C
l1z Cal14Bu4-4MeCOOMe
tl OHCHz CJ140CFzCt(F
z-4MeCOOMe II Otl C1
1z C6C61InSi:+-4MeCOOEt
II OIf Cl1z C611a
COC611aCOOBu-t-4It OHCII
Z C6+14-(C3-CN-1)-4 ecO
OEt tl OII Cl1z
CJI4SCPzCF2CP3-4MeCO
OIEt II OIt Cl12 C
611nCOC611nCON(Pr-i)z-4HO
II ClI2 C614COOu-tMeC
OOPr-i It Otl Cth C
6IIxCOOBu-t-4MeCOOPr-i H
OHCH2CJ4COO-(C4)-4MeCOOBu
-t If OIt C11z CJIa
COOBu-t-4MeCOO13u-t If
OIt CHz C611aOCFzC611
aOCFzCIIFz II OIt C11
z c6114nu-t-'iMeCOOBu
HOII C11z CJI4COOBu-
t-4MeCOOBu II OIf C
l12C6C6l1nSi:+Q1 to Q57 in Table 1 above are groups represented by the following structural formula.
次に本発明化合物の製造方法について実施例を具体的に
挙げて説明するが、本発明はこれらのみにび長足される
ものではない。Next, the method for producing the compound of the present invention will be explained with specific examples, but the present invention does not extend beyond these examples.
太遣■上 ４−（（３−クロル−１−メチル−５−フェ
ノキシピラゾール−４−イル）
メチレンアミノオキシメチル〕安息香
酸Ｌ−ブチルエステル（本発明化合物
Ｎｏ、 １ ）
３−クロル−１−メチル−５−フェノキシピラゾール−
４−アルデヒドオキシム１．２６ ｇと４−ブロモメチ
ル安息香酸−Ｌ−ブチルエステル１．５０ｇをＮ、Ｎ−
ジメチルホルムアミド２５ｍＡに溶解し、炭酸カリウム
０．７５ ｇを加え７０°Ｃで２時間攪拌した。この溶
液を氷水中に注ぎ、エーテルで抽出し、有機層を水洗、
無水硫酸ナトリウムで乾燥後減圧上溶媒を留去し、得ら
れた油状物をカラムクロマトグラフィー（シリカゲル−
ベンゼン）で精製し、目的物を１．６ｇ得た。ｎｏ＝１
．５６３８’ＩＩ−ＮＭＲ（ＣＤＣｊｌ！ ３１ δ
、ＴＭＳ）：１．５７（ｓ、９１１）、 ３．５９（ｓ
、３Ｈ）、 ４．８５（ｓ、２８）。4-((3-chloro-1-methyl-5-phenoxypyrazol-4-yl)methyleneaminooxymethyl]benzoic acid L-butyl ester (invention compound No. 1) 3-chloro-1- Methyl-5-phenoxypyrazole-
1.26 g of 4-aldehydoxime and 1.50 g of 4-bromomethylbenzoic acid-L-butyl ester were mixed with N,N-
The mixture was dissolved in 25 mA of dimethylformamide, 0.75 g of potassium carbonate was added, and the mixture was stirred at 70°C for 2 hours. This solution was poured into ice water, extracted with ether, and the organic layer was washed with water.
After drying over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and the resulting oil was subjected to column chromatography (silica gel-
benzene) to obtain 1.6 g of the desired product. no=1
．． 5638'II-NMR (CDCjl! 31 δ
, TMS): 1.57 (s, 911), 3.59 (s
, 3H), 4.85 (s, 28).
６．７５〜７．９０（ｍ、 １０ｔｌ）以下、製造例１
に準じて製造した化合物の物性を第２表に示す。〔ただ
し、表中の表記は第１表に準する。〕
第２表の化合物の番号は後述する製剤例、試験例におい
て参照される。6.75 to 7.90 (m, 10 tl) or less, Production Example 1
Table 2 shows the physical properties of the compounds produced according to the method. [However, the notation in the table conforms to Table 1. ] The compound numbers in Table 2 are referred to in the formulation examples and test examples described below.
本発明化合物を害虫防除剤として使用するにあたっては
、一般には適当な担体、例えばクレー。For use of the compounds of the invention as pest control agents, a suitable carrier, such as clay, will generally be used.
タルク、ベントナイト珪藻土等の固体担体あるいは水、
アルコール類（メタノール、エタノール等）、芳香族炭
化水素類（ベンゼン、トルエン。A solid carrier such as talc, bentonite diatomaceous earth, or water,
Alcohols (methanol, ethanol, etc.), aromatic hydrocarbons (benzene, toluene, etc.).
キシレン等）、塩素化炭化水素類、エーテル類。xylene, etc.), chlorinated hydrocarbons, and ethers.
ケトン類、エステルＲ（酢酸エチル類）、酸アミド類（
ジメチルホルムアミド等）などの液体担体と混用して適
用することができ、所望により乳化剤２分散剤、懸濁剤
、浸透剤、展着剤、安定剤などを添加し、乳剤、油剤、
水和剤２粉剤１粒剤。Ketones, esters R (ethyl acetates), acid amides (
It can be applied by mixing with a liquid carrier such as dimethylformamide (dimethylformamide, etc.), and if desired, emulsifiers, dispersants, suspending agents, penetrants, spreading agents, stabilizers, etc. can be added to form emulsions, oils, etc.
2 hydrating powders, 1 powder.
フロアブル割等任意の剤型にて実用に供することができ
る。また、必要に応じて製剤または散布時に他種の除草
剤、各種殺虫剤、殺菌剤、植物生長調節剤、共力剤など
と混合施用してもよい。本発明化合物の施用薬量は適用
場面、施用時期、施用方法、対象病害虫、栽培作物等に
より差異はあるが一般には有効成分量としでヘクタール
当たり、０．００５〜５０ｋｇ程度が適当である。It can be put to practical use in any dosage form such as flowable. Further, if necessary, other herbicides, various insecticides, fungicides, plant growth regulators, synergists, etc. may be mixed and applied during formulation or spraying. The amount of the compound of the present invention to be applied varies depending on the application situation, application time, application method, target pests, cultivated crops, etc., but in general, the appropriate amount of active ingredient is about 0.005 to 50 kg per hectare.
次に本発明の各種製剤の配合割合および種類を下記に記
載する。Next, the blending ratios and types of various formulations of the present invention are described below.
乳剤 １〜２５５２〜９５３〜２００〜２０油剤 １〜
３０５７〜９９
フロアフル １〜７０ １０〜９０
１〜２０ ０〜１０水和剤 １〜７０１５〜９３
３〜１０ ０〜５粉剤０．０１〜３０６７〜９９．５０
〜３粒剤０．０１〜３０６７〜９９．５ ０〜８上記
の表中の数値は、重量％を表す。Emulsion 1-2552-953-200-20 Oil 1-
3057~99 Floor full 1~70 10~90
1-20 0-10 Hydrating agent 1-7015-93
3-10 0-5 Powder 0.01-3067-99.50
~3 Granules 0.01-3067-99.5 0-8 The numerical values in the above table represent weight %.
施用に際しては、乳剤、油剤、フロアブルおよび水和剤
では所定量の水で希釈して散布し、粉剤および粒剤は水
で希釈することなく、そのまま直接、散布する。When applying, emulsions, oils, flowables, and wettable powders are diluted with a predetermined amount of water before being sprayed, while powders and granules are sprayed directly without being diluted with water.
次に上記の各製剤中の各成分の例を挙げる。Next, examples of each component in each of the above formulations are given.
１尤−
有効成分 二本発明化合物
担 体 ：キシレン、ジメチルホルムアミド、メチル
ナフタレン、シクロヘキサノ
ン、ジクロロベンゼン、イソホロン
界面活性剤：ツルポール２６８０、ツルポール３００５
Ｘ、ツルポール２６８０
その他の成分：ピペロニルブトキサイド、ベンゾトリア
ゾール
前層
有効成分 ：本発明化合物
担 体 ；キシレン、メチルセロソルブ、ケロシン
フロアブル
有効成分 ：本発明化合物
担 体 ：水
界面活性剤ニルノックス１００ＯＣ、ツルポール３３５
３、ソブロファーＰＬ、ニッポール、アグ
リソールＳ−７１０、リグニンスルホン酸ソーダ
その他の成分：ザンサンガム、ホルマリン、エチレング
リコール、プロピレングリコ
ール
水Ｊ旧独
有効成分 二本発明化合物
担 体 ：炭酸カルシウム、カオリナイト、ジークラ
イトＤ１ジークライトＰＰＰ 。1. Active ingredients 2. Compound carrier of the present invention: xylene, dimethylformamide, methylnaphthalene, cyclohexanone, dichlorobenzene, isophorone Surfactant: Tsurpol 2680, Tsurpol 3005
X, Tsurpol 2680 Other ingredients: Piperonyl butoxide, benzotriazole Front layer active ingredients: Compound carrier of the present invention; Xylene, methyl cellosolve, kerosene flowable active ingredients: Compound carrier of the present invention: Water surfactant Nilnox 100OC, Tsurupol 335
3. Sobrofer PL, Nippol, Agrisol S-710, sodium lignin sulfonate Other ingredients: xanthan gum, formalin, ethylene glycol, propylene glycol water J Old German active ingredients 2. Compound carrier of the present invention: Calcium carbonate, kaolinite, Sieg Light D1 Sieglite PPP.
珪藻土、タルク
界面活性剤；ツルポール５０３９、ルノックス１００Ｏ
Ｃ、リグニンスルホン酸カルシウム、ド
デシルベンゼンスルホン酸ソーダ、
ツルポール５０５０、ツルポール００５０゜ツルポール
５０２９−０
その他の成分二カープレックス＃８０
例月
有効成分 ：本発明化合物
担 体 ：炭酸カルシウム、カオリナイト、ジークラ
イトＤ１タルク
その他の成分ニジイソプロピルホスフェート、カープレ
ックス＃８０
粒重Ｙ
有効成分 ：本発明化合物
担体：炭酸カルシウム、カオリナイト、ベントナイト、
タルク
その他の成分：リグニンスルホン酸カルシウム、ポリビ
ニールアルコール
次に本発明化合物を有効成分とする殺虫、殺ダニ、殺線
虫剤および動物に寄生するダニの駆除剤の製剤例を示す
がこれらのみに限定されるものではない。なお、以下の
製剤例において１部」は重量部を意味する。Diatomaceous earth, talc surfactant; Tsurupol 5039, Lunox 100O
C, calcium lignin sulfonate, sodium dodecylbenzenesulfonate, Tsurupol 5050, Tsurupol 0050゜Tsurpol 5029-0 Other ingredients Nicarplex #80 Monthly active ingredients: Compound of the present invention Carrier: Calcium carbonate, kaolinite, Siegrite D1 talc Other ingredients Nidiisopropyl phosphate, Carplex #80 Particle weight Y Active ingredients: Compound of the present invention Carrier: Calcium carbonate, kaolinite, bentonite,
Talc and other ingredients: Calcium ligninsulfonate, polyvinyl alcohol Next, examples of formulations of insecticides, acaricides, nematicides, and insecticides for killing mites parasitic on animals that contain the compounds of the present invention as active ingredients are shown below. It is not limited. In addition, in the following formulation examples, "1 part" means parts by weight.
裂」１例」−乳剤
本発明化合物 −・−−一−−−−−−〜
−−−・・ ５部キシレン −−−−
−−・−・・・−７０部Ｎ、Ｎ−ジメチルホルムアミド
−・−−一−−−−−−−・−・ ２０部ツルポール２
６８０ −−−−−−一・ ５部（非イオン性界
面活性剤とアニオン性界面活性剤との混合物：東邦化学
工業■標品名）
以上を均一に混合して乳剤とする。使用に際しては上記
乳剤を５０〜２００００倍に希釈して有効成分量かへク
タール当たり０．００５〜５０ｋｇになるように散布す
る。Example 1 of "Crack" - Emulsion Compound of the Present Invention -・--1-----
---... 5 parts xylene ---
---・--70 parts N,N-dimethylformamide-----1-----20 parts Tsurpol 2
680 --- 1.5 parts (Mixture of nonionic surfactant and anionic surfactant: Toho Chemical Industry ■Standard name) The above is mixed uniformly to form an emulsion. When used, the above emulsion is diluted 50 to 20,000 times and sprayed at an amount of active ingredient of 0.005 to 50 kg per hectare.
製剋１ 水和剤
本発明化合物 −−−一−−−・・・−−
一−−−・ ２５部ジークライトＰＦＰ ・−
−−−−−−−−・・−・・ ６６部（カオリナイトと
セリサイトの混合物：ジークライト工業■商品名）
ツルポール５０３９ −・−−−−−−−−−−−
−４部（アニオン性界面活性剤：
東邦化学工業Ｑ勾商品名）
カープレックス＃８０ −−−−−−−−−−−−
−・−３部（ホワイトカーボン：塩野義製薬■商品名）
リグニンスルホン酸カルシウムー−−一−・・・−−−
２部以上を均一に混合粉砕して水和剤とする。Preparation 1 Wettable powder Compound of the present invention ---1-----...-
1---- Part 25 Sieglite PFP ・-
−−−−−−−−・・−・・ 66 parts (Mixture of kaolinite and sericite: Zeeklite Kogyo ■Product name) Tsurupol 5039 −・−−−−−−−−−−
-4 parts (anionic surfactant: Toho Chemical Industry Q-Ko product name) Carplex #80 -----------------------
-・- Part 3 (White Carbon: Shionogi & Co. ■Product name)
Calcium lignin sulfonate - - - - - -
Two or more parts are uniformly mixed and ground to make a wettable powder.
使用に際しては上記水和剤を５０〜２００００倍に希釈
して有効成分量かへクタール当たり０．００５〜５０ｋ
ｇになるように散布する。When using, dilute the above hydrating agent 50 to 20,000 times to obtain an active ingredient amount of 0.005 to 50 k per hectare.
Spread it so that it becomes g.
製」Ｗ例Ｊ−油剤
本発明化合物 −−−−−−−−−−−１
０部メチルセルソブル −ヘー・−−−−−−
−−９０部以上を均一に混合して油剤とする。使用に際
して上記油剤を有効成分量かへクタール当たり０．００
５〜５０ｋｇになるように散布する。"W Example J - Oil agent Compound of the present invention ----------------------1
0 parts Methyl Celsoblu - Heh -------
--90 parts or more are uniformly mixed to form an oil agent. When using the above oil, the amount of active ingredient is 0.00 per hectare.
Spread it to a weight of 5 to 50 kg.
１６１例」工粉剤
本発明化合物 ・−−−−−−−−−−−
−−３，０部カープレックス＃８０ −−−−一・
−一一一−−・−０，５部（ホワイトカーボン：塩野義
製薬味商品名）クレー −・・・・−
・・−−−−−−−９５部リン酸ジイソプロピル
−−−−−−−１、５部以上を均一に混合粉砕して粉剤
とする。使用に際して上記粉剤を有効成分量がヘクリー
ル当たり０．００５〜５０ｋｇになるように散布する。Example 161” Compound of the present invention as a powder agent
--3,0 copies Carplex #80 ---1.
−111−−・−0.5 parts (white carbon: Shionogi Pharmaceutical flavor product name) clay −・・−
・・・95 parts diisopropyl phosphate
------- 1.5 parts or more are uniformly mixed and pulverized to form a powder. During use, the above-mentioned powder is spread so that the amount of active ingredient is 0.005 to 50 kg per heclyl.
朋肛粒剤
本発明化合物 −−−−−−−一・−−−
−−−−５部ベントナイト −−−−−−
−−・−−−−−５４部タルク −
−−−−−−−−−−−−−４０部リグニンスルホン酸
カルシウム−−−〜−−−−−−−１部以上を均一に混
合粉砕して少量の水を加えて攪拌混合し、押出式造粒機
で造粒し、乾燥して粒剤とする。使用に際して上記粒剤
を有効成分量かへクタール当たり０．００５〜５０ｋｇ
になるように散布する。Anal granules Compound of the present invention -------1・----
−−−−5 parts bentonite −−−−−−
−−・−−−−54 parts talc −
−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−) Granulate with an extrusion granulator and dry to form granules. When using the above granules, the amount of active ingredient is 0.005 to 50 kg per hectare.
Spread it so that
裂■■旦 フロアブル剤
本発明化合物 −・−−−−−−３５部ツ
ルポール３３５３ −−−−−−−− １０部（
非イオン性界面活性剤：東邦化学工業Ｑ勾商品名）ルノ
ックス１００ＯＣ・−・−−−−−−一−・−・−０，
５部（陰イオン界面活性剤：東邦化学工業側商品名）１
％ザンサンガム水溶液 −−−−−・−・・−・・・
−２０部（天然高分子）
水 −−−−・−・・
・・・−・ ３４．５ 部有効成分（本発明化合物）を
除く上記の成分を均一に溶解し、ついで本発明化合物を
加えよく攪拌した後、サンドミルにて湿式粉砕してフロ
アブル剤を得る。使用に際しては、上記フロアブル剤を
５０〜２００００倍に希釈して有効成分量かへクタール
当たり０．００５〜５０ｋｇになるように散布する。Flowable agent Compound of the present invention --- 35 parts Tsurupol 3353 --- 10 parts (
Nonionic surfactant: Toho Chemical Co., Ltd. Q-gradation product name) Lunox 100OC・−・−−−−−−1−・−・−0,
5 parts (anionic surfactant: Toho Chemical Industry brand name) 1
% xanthan gum aqueous solution −−−−−・−・・−・・
−20 parts (natural polymer) Water −−−−・−・・
34.5 parts The above components except for the active ingredient (the compound of the present invention) are uniformly dissolved, and then the compound of the present invention is added and stirred well, followed by wet grinding in a sand mill to obtain a flowable agent. When used, the above-mentioned flowable agent is diluted 50 to 20,000 times and sprayed at an amount of active ingredient of 0.005 to 50 kg per hectare.
本発明化合物は、害虫防除剤として有用であり特に農業
用殺虫・殺ダニ・殺線虫剤、衛生害虫防除剤および動物
に寄生するダニの駆除剤として有用である。更に具体的
には、ツマグロヨコバイ等の半翅目害虫、コナガ等の燐
翅目害止、鞘翅目害虫、アカイエカ等の衛生害虫に卓越
した殺虫力を有するとともに、果樹および倣菜に寄生す
る種々のダニ、例えば、ナミハダニ、カンザワハダニ、
ニセナミハダニ、ミカンハダニ、リンゴハダニ等および
動物に寄生するダニ例えば、オウシマダニ、ブーフィラ
ス・アニュレイタス、アンプリオンマ・マクレイタム、
リビセファラス・アベンディクラータス、フタトゲチマ
ダニ等の防除にも有効である。The compound of the present invention is useful as a pest control agent, particularly as an agricultural insecticide, acaricide, or nematicide, a sanitary pest control agent, and an agent for controlling mites parasitic on animals. More specifically, it has excellent insecticidal power against Hemiptera pests such as leafhoppers, Phosphoroptera pests such as the diamondback moth, Coleoptera pests, and sanitary pests such as Culex mosquito, as well as various insecticides that parasitize fruit trees and imitation vegetables. Mites, such as two-spotted spider mites, Kanzawa spider mites,
Locust spider mite, citrus spider mite, apple spider mite, etc., and mites parasitic on animals, such as the American spider mite, Boophilus annullitus, Amplionma maculatum,
It is also effective in controlling Libicephalus avendiculatus, Phyllis tick, etc.
次に、本発明化合物の害虫防除剤としての有用性につい
て、以下の試験例において具体的に説明する。Next, the usefulness of the compound of the present invention as a pest control agent will be specifically explained in the following test examples.
ＭＪＩＵＩ上 ツマグロヨコバイに対する殺虫試験明細
書に記載された本発明化合物の５％乳剤（化合物によっ
ては２５％永和剤を供試）を展着剤の入った水で希釈し
て、１１０００ｐｐ濃度の薬液に調整した。この薬液を
１／２００００アールのポットに植えたイネの茎葉に十
分量散布し、風乾後、有機リン系殺虫剤およびカーバメ
ート系殺虫剤に抵抗性を示すツマグロヨコバイの２令幼
虫をポットあたり２０頭放虫し、そのイネに金網の円筒
ゲージをかぶせて恒温室に保管した。調査は９６時間経
過後に行い死出率を下記の計算式から求めた。On MJIUI A 5% emulsion of the compound of the present invention (a 25% permanent agent is used depending on the compound) described in the insecticidal test specification against black leafhopper was diluted with water containing a spreading agent to make a chemical solution with a concentration of 11,000 pp. did. A sufficient amount of this chemical solution was sprayed on the stems and leaves of rice planted in a 1/20,000 are pot, and after air-drying, 20 second-instar larvae of the black leafhopper, which is resistant to organophosphorus insecticides and carbamate insecticides, were released per pot. After insect infestation, the rice was covered with a cylindrical cage made of wire mesh and stored in a constant temperature room. The investigation was conducted after 96 hours had elapsed, and the mortality rate was calculated using the following formula.
なお、試験は２区制で行なった。The test was conducted in two sections.
その結果、以下の化合物が１００％の死生率を示した。As a result, the following compounds showed a 100% mortality rate.
本発明化合物 Ｎα１、Ｎα２、Ｎｏ、 ４、Ｎα５、
Ｎｏ、 ８、Ｎｏ、 １０
Ｂ３剣例」−ニジュウヤホシテントウに対する殺虫試験
明細書に記載された本発明化合物の５％乳剤（化合物に
よっては２５％永和剤を供試）を展着剤の入った水で希
釈して、１１０００ｐｐ濃度の薬液に調整しこの薬液中
にトマトの葉を約１０秒間浸漬し、風乾後シャーレに入
れ、この中にニジュウヤホシテントウ２令幼虫をシャー
レ当たり１０頭を放出し、孔のあいた蓋をして２５°Ｃ
恒温室に収容し、９６時間経過後の死生率を下記の計算
式から求めた。なお、試験は２区制で行なった。Compounds of the present invention Nα1, Nα2, No, 4, Nα5,
No. 8, No. 10 B3 Example" - A 5% emulsion of the compound of the present invention (25% permanent agent was tested depending on the compound) described in the specification of the insecticidal test against the Japanese lady beetle was mixed with a spreading agent. Tomato leaves were immersed in this chemical solution for about 10 seconds, air-dried, and then placed in a petri dish. Into this, 2nd instar nymphs of the ladybug were placed in a petri dish, 10 larvae per petri dish. Drain, cover with perforated lid and heat at 25°C.
The mice were housed in a constant temperature room, and the mortality rate after 96 hours was calculated using the following formula. The test was conducted in two sections.
死虫数 死生率（％） ＝ −Ｘ １００ 放虫数 その結果、以下の化合物が１００％の死生率を示した。Number of dead insects Mortality rate (%) = -X 100 Number of insects released As a result, the following compounds showed a 100% mortality rate.
本発明化合物 Ｎｏ、 １、Ｎｏ、 ２、Ｎｏ、 ４、
Ｎ（１５、Ｎ０１６、Ｎｏ、 ８、Ｎｏ、１０． Ｎｏ
、１１跋駄開１ カンザワハダニに対する殺ダニ効力
試験
インゲンの葉をリーフパンチを用いて径１．５ ｃｍの
円形に切り取り、径７ｃｍのスチロールカップ上の湿っ
た濾紙上に置いた。これにカンザワハダニ幼虫を１葉当
たり１０頭接種した。接種半日後に明細書に記載された
本発明化合物の５％乳剤（化合物によっては２５％永和
剤を供試）を展着剤の入った水で希釈して、１１０００
ｐｐ濃度の薬液に調整しこの薬液をスチロールカップ当
たり２ ｍｅずつ回転式散布塔を用いて散布し、９６時
間経過後の死生率を下記の計算式から求めた。なお、試
験は２区制で行なった。Compounds of the present invention No. 1, No. 2, No. 4,
N(15, N016, No, 8, No, 10. No
Acaricidal efficacy test against Kanzawa spider mites Green bean leaves were cut into circles with a diameter of 1.5 cm using a leaf punch and placed on moist filter paper on a styrene cup with a diameter of 7 cm. This was inoculated with 10 Kanzawa spider mite larvae per leaf. Half a day after inoculation, a 5% emulsion of the compound of the present invention described in the specification (25% permanant is used depending on the compound) was diluted with water containing a spreading agent to give 11,000% emulsion.
The chemical solution was adjusted to a pp concentration and was sprayed at a rate of 2 me per styrene cup using a rotary scattering tower, and the mortality rate after 96 hours was determined from the following formula. The test was conducted in two sections.
その結果、以下の化合物が１００％の死生率を示した。As a result, the following compounds showed a 100% mortality rate.
本発明化合物 Ｎ０１１、Ｎ０９２、Ｎα３、Ｎ０９４
、Ｎ０１５、Ｎｏ、 ６、Ｎ００７、ＮＯ１９、Ｎ（Ｌ
ＩＯｌＮｏ、 １１、Ｎｏ、 １２、Ｎｏ、 １３
拭狂尉土 キュウリうどんこ病防除試験２週間鉢で育成
したキュウリ（品種：組構半白）を用い、本発明化合物
乳剤を所定濃度に調製した薬液（１０００ｐｐｍ）を鉢
当たり２０ｍ２散布した。このキュウリを温室内に一昼
装置きキュウリうどんこ病菌（Ｓｐｈａｅｒｏｔｈｅｃ
ａ ｆｕｌｉｇｉｎｅａ）の胞子懸濁液（１５０倍で１
視野に２５個の胞子）を噴霧し接種を行った。このキュ
ウリを２５〜３０°Ｃの温室に置き発病を待った。接種
１０日経過後の罹病度を調査した。その結果、以下の化
合物の場合に全く発病を認めなかった。Compounds of the present invention N011, N092, Nα3, N094
, N015, No. 6, N007, NO19, N(L
IOlNo., 11, No., 12, No., 13 Fukyusoto Cucumber Powdery Mildew Control Test Using cucumbers (variety: Kisetsu Hanshiro) grown in pots for 2 weeks, a chemical solution containing an emulsion of the compound of the present invention at a predetermined concentration. (1000 ppm) was sprayed in 20 m2 per pot. The cucumbers were kept in a greenhouse for one day and were infected with cucumber powdery mildew fungus (Sphaerothec).
A fuliginea) spore suspension (150x magnification)
Inoculation was performed by spraying the field with 25 spores. The cucumbers were placed in a greenhouse at 25 to 30°C to wait for the onset of disease. The degree of morbidity was investigated 10 days after inoculation. As a result, no symptoms were observed with the following compounds.
本発明化合物 Ｎ０９１
試邊影例」−コムギ赤さび病防除効果試験直径９ ｃｍ
のポットで育成したコムギ（農林６１号、３〜４葉３ｔ
Ｊ］）に、本発明化合物乳剤を１１０００ｐｐの濃度に
調製した薬液を、スプレーガンを用いてポンド当たり２
０ｍｊ２散布した。散布翌日、コムギ赤さび病菌（ｐｕ
（（ｉｎｉａｒｅｃｏｎｄｉｔａ）夏胞子懸濁液（Ｘ１
５０．３０個／視野）を噴霧し、温度２５°Ｃ１湿度９
５％以上の接種箱に一昼夜入れた。その後温室に置き、
接種１０日後に形成された病斑面積を測定し、下記の式
に従い防除価を算出した。Compound of the present invention N091 Test image example - Wheat rust control effect test Diameter 9 cm
Wheat grown in a pot (Norin No. 61, 3-4 leaves, 3 tons)
J]), a chemical solution prepared by preparing an emulsion of the compound of the present invention to a concentration of 11,000 pp was added to 2 kg per pound using a spray gun.
Sprayed 0mj2. The day after spraying, wheat rust fungus (pu
((iniarecondita) summer spore suspension (X1
50.30 pieces/view), temperature 25°C, humidity 9
They were placed in a 5% or higher inoculation box overnight. Then place it in a greenhouse
The area of lesions formed 10 days after inoculation was measured, and the control value was calculated according to the following formula.
その結果、以下の化合物は１００％の防除価を示した。As a result, the following compounds showed 100% control value.
本発明化合物 Ｎｏ、 １ 特許出願人 日産化学工業株式会社Compound of the present invention No. 1 Patent applicant: Nissan Chemical Industries, Ltd.
Claims (2)
のアルケニル基、炭素数２〜６のアルキニル基、炭素数
３〜６のシクロアルキル基またはフェニル基を表し、 Ｒ＾１はハロゲン原子、炭素数１〜４のアルコキシ基、
炭素数１〜４のアルコキシカルボニル基、シアノ基また
はニトロ基を表し、 Ｒ＾２は、水素原子、炭素数１〜４のアルキル基または
フェニル基を表し、 Ｘは、酸素原子または硫黄原子を表し、 Ｙは、水素原子、ハロゲン原子、炭素数１〜６のアルキ
ル基、炭素数１〜４のハロアルキル基、炭素数１〜４の
アルコキシ基、炭素数１〜４のハロアルコキシ基、炭素
数１〜３のアルキレンジオキシ基、フェノキシ基、−Ｓ
（Ｏ）＿ｎＲ＾３基（但し、Ｒ＾３は炭素数１〜４のア
ルキル基または炭素数１〜４のハロアルキル基を示し、
ｎは０、１または２を表す。）、−ＣＯＯＲ＾４基（但
し、Ｒ＾４は炭素数１〜６のアルキル基、炭素数３〜６
のシクロアルキル基または炭素数２〜６のアルケニル基
を表す。）または▲数式、化学式、表等があります▼（
但し、Ｒ＾５およびＲ＾６はそれぞれ独立に水素原子ま
たは炭素数１〜６のアルキル基を表す。）を表し、 ｍは１、２または３を表し、 Ａは、▲数式、化学式、表等があります▼基、▲数式、
化学式、表等があります▼基、▲数式、化学式、表等が
あります▼基、 ▲数式、化学式、表等があります▼基、▲数式、化学式
、表等があります▼基、（但し、Ｒ＾７、Ｒ＾８および
Ｒ＾９はそれぞれ独立に水素原子または炭素数１〜４の
アルキル基を表す。）を表し、 Ｑは、置換されていてもよいフェニル基または置換され
ていてもよい複素環基を表す。〕で表されるピラゾール
オキシム誘導体。(1) General formula [I]: ▲There are mathematical formulas, chemical formulas, tables, etc.▼[I] [In the formula, R is an alkyl group having 1 to 6 carbon atoms, or an alkyl group having 2 to 6 carbon atoms.
represents an alkenyl group, an alkynyl group having 2 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or a phenyl group, R^1 is a halogen atom, an alkoxy group having 1 to 4 carbon atoms,
represents an alkoxycarbonyl group, cyano group, or nitro group having 1 to 4 carbon atoms, R^2 represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a phenyl group, and X represents an oxygen atom or a sulfur atom. , Y is a hydrogen atom, a halogen atom, an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a haloalkoxy group having 1 to 4 carbon atoms, or a haloalkoxy group having 1 to 4 carbon atoms. -3 alkylenedioxy group, phenoxy group, -S
(O)_nR^3 group (where R^3 represents an alkyl group having 1 to 4 carbon atoms or a haloalkyl group having 1 to 4 carbon atoms,
n represents 0, 1 or 2. ), -COOR^4 group (however, R^4 is an alkyl group having 1 to 6 carbon atoms, 3 to 6 carbon atoms
represents a cycloalkyl group or an alkenyl group having 2 to 6 carbon atoms. ) or ▲Mathematical formulas, chemical formulas, tables, etc.▼(
However, R^5 and R^6 each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. ), m represents 1, 2, or 3, A represents ▲mathematical formula, chemical formula, table, etc.▼group, ▲mathematical formula,
There are chemical formulas, tables, etc. ▼ Groups, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ Groups, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ Groups, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ Groups (However, R^ 7, R^8 and R^9 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and Q is an optionally substituted phenyl group or an optionally substituted hetero Represents a ring group. ] A pyrazole oxime derivative represented by
有効成分として含有する殺虫、殺ダニ、殺菌剤。(2) An insecticide, acaricide, or bactericide containing one or more of the compounds according to claim 1 as an active ingredient.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2245488A JPH01197471A (en) | 1988-02-02 | 1988-02-02 | Pyrazole oxime derivative and insecticide, acaricide and germicide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2245488A JPH01197471A (en) | 1988-02-02 | 1988-02-02 | Pyrazole oxime derivative and insecticide, acaricide and germicide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH01197471A true JPH01197471A (en) | 1989-08-09 |
Family
ID=12083158
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2245488A Pending JPH01197471A (en) | 1988-02-02 | 1988-02-02 | Pyrazole oxime derivative and insecticide, acaricide and germicide |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01197471A (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015064725A1 (en) * | 2013-10-31 | 2015-05-07 | 住友化学株式会社 | Pyrazole compound and pest control application thereof |
| CN106946856A (en) * | 2017-02-08 | 2017-07-14 | 南通大学 | Pyrazoles 9 oxime derivate of the biphenyl structures containing tetrazole and its production and use |
| CN108976221A (en) * | 2018-07-23 | 2018-12-11 | 南通大学 | Pyrazoles oxime ether compound of the biphenyl structures of oxadiazoles containing 1,3,4- and its preparation method and application |
| CN109879866A (en) * | 2019-02-02 | 2019-06-14 | 南通大学 | A kind of preparation and application of the pyrazoles oxime derivatives of the sulfenyl of biphenyl containing oxazole structure |
| CN110003184A (en) * | 2019-02-01 | 2019-07-12 | 南通大学 | The preparation and application of pyrazoles oxime derivatives of the one kind containing 1,2,4- triazole structures |
| CN110305115A (en) * | 2019-08-19 | 2019-10-08 | 南通大学 | The preparation and application of pyrazoles 9 oxime derivate of the one kind containing 1- (6- chloropyrazine -2- base) -3- methoxyl group pyrazoles unit |
| CN110372674A (en) * | 2019-08-22 | 2019-10-25 | 南通大学 | The preparation and application of the pyrazole compound of the unit containing benzotriazole |
| CN111423413A (en) * | 2020-05-12 | 2020-07-17 | 南通大学 | Preparation and application of pyrazole derivative containing (3-methoxy-4-substituted pyridylmethoxy) phenyl unit |
-
1988
- 1988-02-02 JP JP2245488A patent/JPH01197471A/en active Pending
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015064725A1 (en) * | 2013-10-31 | 2015-05-07 | 住友化学株式会社 | Pyrazole compound and pest control application thereof |
| CN106946856A (en) * | 2017-02-08 | 2017-07-14 | 南通大学 | Pyrazoles 9 oxime derivate of the biphenyl structures containing tetrazole and its production and use |
| CN108976221A (en) * | 2018-07-23 | 2018-12-11 | 南通大学 | Pyrazoles oxime ether compound of the biphenyl structures of oxadiazoles containing 1,3,4- and its preparation method and application |
| CN110003184A (en) * | 2019-02-01 | 2019-07-12 | 南通大学 | The preparation and application of pyrazoles oxime derivatives of the one kind containing 1,2,4- triazole structures |
| CN109879866A (en) * | 2019-02-02 | 2019-06-14 | 南通大学 | A kind of preparation and application of the pyrazoles oxime derivatives of the sulfenyl of biphenyl containing oxazole structure |
| CN109879866B (en) * | 2019-02-02 | 2022-04-22 | 南通大学 | Preparation and application of pyrazole oxime derivative containing oxazole biphenyl sulfenyl structure |
| CN110305115A (en) * | 2019-08-19 | 2019-10-08 | 南通大学 | The preparation and application of pyrazoles 9 oxime derivate of the one kind containing 1- (6- chloropyrazine -2- base) -3- methoxyl group pyrazoles unit |
| CN110372674A (en) * | 2019-08-22 | 2019-10-25 | 南通大学 | The preparation and application of the pyrazole compound of the unit containing benzotriazole |
| CN110372674B (en) * | 2019-08-22 | 2021-04-30 | 南通大学 | Preparation and application of pyrazole compound containing benzotriazole unit |
| CN111423413A (en) * | 2020-05-12 | 2020-07-17 | 南通大学 | Preparation and application of pyrazole derivative containing (3-methoxy-4-substituted pyridylmethoxy) phenyl unit |
| CN111423413B (en) * | 2020-05-12 | 2022-06-03 | 南通大学 | Preparation and application of pyrazole derivative containing (3-methoxy-4-substituted pyridylmethoxy) phenyl unit |
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