JP5728540B2 - 新規な化合物 - Google Patents
新規な化合物 Download PDFInfo
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- JP5728540B2 JP5728540B2 JP2013171615A JP2013171615A JP5728540B2 JP 5728540 B2 JP5728540 B2 JP 5728540B2 JP 2013171615 A JP2013171615 A JP 2013171615A JP 2013171615 A JP2013171615 A JP 2013171615A JP 5728540 B2 JP5728540 B2 JP 5728540B2
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- 150000001875 compounds Chemical class 0.000 title claims description 227
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 83
- 238000004519 manufacturing process Methods 0.000 claims description 81
- 239000003795 chemical substances by application Substances 0.000 claims description 39
- 125000005843 halogen group Chemical group 0.000 claims description 39
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
- 125000001153 fluoro group Chemical group F* 0.000 claims description 25
- 229910052731 fluorine Inorganic materials 0.000 claims description 24
- 125000002560 nitrile group Chemical group 0.000 claims description 21
- 229910052801 chlorine Inorganic materials 0.000 claims description 17
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 13
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 230000002140 halogenating effect Effects 0.000 claims description 10
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 5
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 3
- -1 amide compounds Chemical class 0.000 description 115
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 63
- 238000000034 method Methods 0.000 description 62
- 150000001408 amides Chemical class 0.000 description 61
- 239000002904 solvent Substances 0.000 description 56
- 238000006243 chemical reaction Methods 0.000 description 47
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 42
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
- 241000607479 Yersinia pestis Species 0.000 description 33
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
- 238000005160 1H NMR spectroscopy Methods 0.000 description 27
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 24
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- 230000008569 process Effects 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
- 241000254173 Coleoptera Species 0.000 description 21
- 239000003054 catalyst Substances 0.000 description 20
- 239000000203 mixture Substances 0.000 description 19
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 16
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 16
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 15
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 14
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 14
- 125000004432 carbon atom Chemical group C* 0.000 description 14
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
- 150000002148 esters Chemical class 0.000 description 13
- 239000000843 powder Substances 0.000 description 13
- 230000035484 reaction time Effects 0.000 description 13
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 12
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- 241000238631 Hexapoda Species 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 239000004480 active ingredient Substances 0.000 description 12
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical class OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 12
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
- 241000238876 Acari Species 0.000 description 11
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 11
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 11
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 11
- 239000002585 base Substances 0.000 description 11
- 230000000694 effects Effects 0.000 description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 11
- 150000002576 ketones Chemical class 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 239000008096 xylene Substances 0.000 description 11
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 10
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 10
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- 150000002825 nitriles Chemical class 0.000 description 10
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 10
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 9
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 125000001424 substituent group Chemical group 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 8
- 241000244206 Nematoda Species 0.000 description 8
- 241001674048 Phthiraptera Species 0.000 description 8
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 8
- 150000001299 aldehydes Chemical class 0.000 description 8
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 8
- 150000004292 cyclic ethers Chemical class 0.000 description 8
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 8
- 241000239290 Araneae Species 0.000 description 7
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 7
- 241000196324 Embryophyta Species 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- 150000001298 alcohols Chemical class 0.000 description 7
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 7
- 125000004104 aryloxy group Chemical group 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- 239000008187 granular material Substances 0.000 description 7
- 150000008282 halocarbons Chemical class 0.000 description 7
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 7
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 229910052938 sodium sulfate Inorganic materials 0.000 description 7
- 235000011152 sodium sulphate Nutrition 0.000 description 7
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 7
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical group ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 6
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 6
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 6
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 241001414720 Cicadellidae Species 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
- 241000255925 Diptera Species 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 150000008065 acid anhydrides Chemical class 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 6
- 235000013312 flour Nutrition 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 6
- NASBMBLBQGTQKO-UHFFFAOYSA-N methyl 3-amino-2-fluorobenzoate;hydrochloride Chemical compound Cl.COC(=O)C1=CC=CC(N)=C1F NASBMBLBQGTQKO-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 description 5
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 5
- OGMQJQFBXQXEMF-UHFFFAOYSA-N 3-[benzoyl(methyl)amino]-2-fluorobenzoic acid Chemical compound C=1C=CC(C(O)=O)=C(F)C=1N(C)C(=O)C1=CC=CC=C1 OGMQJQFBXQXEMF-UHFFFAOYSA-N 0.000 description 5
- 241000566547 Agrotis ipsilon Species 0.000 description 5
- 241000256837 Apidae Species 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 241000256602 Isoptera Species 0.000 description 5
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical class CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 5
- 229910019142 PO4 Inorganic materials 0.000 description 5
- 230000009471 action Effects 0.000 description 5
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 5
- 235000020971 citrus fruits Nutrition 0.000 description 5
- 229940117389 dichlorobenzene Drugs 0.000 description 5
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 5
- 239000012442 inert solvent Substances 0.000 description 5
- 229910001512 metal fluoride Inorganic materials 0.000 description 5
- 235000021317 phosphate Nutrition 0.000 description 5
- 239000002798 polar solvent Substances 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 239000004563 wettable powder Substances 0.000 description 5
- 239000002023 wood Substances 0.000 description 5
- NMPVEAUIHMEAQP-UHFFFAOYSA-N 2-Bromoacetaldehyde Chemical compound BrCC=O NMPVEAUIHMEAQP-UHFFFAOYSA-N 0.000 description 4
- OVNMDSWQBKOQBF-UHFFFAOYSA-N 2-bromo-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-6-(trifluoromethyl)aniline Chemical compound NC1=C(Br)C=C(C(F)(C(F)(F)F)C(F)(F)F)C=C1C(F)(F)F OVNMDSWQBKOQBF-UHFFFAOYSA-N 0.000 description 4
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 4
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 description 4
- 241000283690 Bos taurus Species 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- 241000238424 Crustacea Species 0.000 description 4
- 241000254171 Curculionidae Species 0.000 description 4
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 241000256247 Spodoptera exigua Species 0.000 description 4
- 241000270666 Testudines Species 0.000 description 4
- 125000004423 acyloxy group Chemical group 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 239000000428 dust Substances 0.000 description 4
- 230000009969 flowable effect Effects 0.000 description 4
- 230000003301 hydrolyzing effect Effects 0.000 description 4
- 239000002917 insecticide Substances 0.000 description 4
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 4
- KFVDQAUKLNZXPD-UHFFFAOYSA-N methyl 3-benzamido-2-fluorobenzoate Chemical compound COC(=O)C1=CC=CC(NC(=O)C=2C=CC=CC=2)=C1F KFVDQAUKLNZXPD-UHFFFAOYSA-N 0.000 description 4
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 239000003880 polar aprotic solvent Substances 0.000 description 4
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 description 4
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Description
また、本発明にかかるアミド誘導体を製造する上での有用な中間体を見出し、本発明を完成するに至ったものである。
すなわち、本発明は以下の通りである。
<1> 下記一般式(1)
<2> 前記一般式(2)において、LGで表される脱離基がハロゲン原子である前記<1>に記載のアミド誘導体の製造方法。
<3> 前記一般式(3)で表されるアミド誘導体が、下記一般式(4)
<4> 下記一般式(5)
<6> 前記一般式(5)におけるR2が水素原子である化合物を、下記一般式(10)
<8> 前記一般式(11)で表される化合物を、下記一般式(12)
<9> 前記一般式(3)で表されるアミド誘導体が、下記一般式(20)
<10> 下記一般式(8)
<11> 下記一般式(12)
「ハロゲン原子」とは、フッ素原子、塩素原子、臭素原子またはヨウ素原子を示す。
「Ca−Cb(a、bは1以上の整数を表す)」との表記、例えば、「C1−C3」とは炭素原子数が1〜3個であることを意味し、「C2−C6」とは炭素原子数が2〜6個であることを意味する。
「n−」とはノルマルを意味し、「i−」はイソを意味し、「s−」はセカンダリーを意味し、「t−」はターシャリーを意味する。
「C1−C6アルキル基」とは例えば、メチル、エチル、n−プロピル、i−プロピル、n−ブチル、i−ブチル、s−ブチル、t−ブチル、n−ペンチル、i−ペンチル、ネオペンチル、4−メチル−2−ペンチル、n−ヘキシル、3−メチル−n−ペンチル等の直鎖状または分岐状の炭素原子数が1〜6のアルキル基を表す。
「C2−C6アルケニル基」とは例えば、ビニル、1−プロペニル、アリル、イソプロペニル、1−ブテニル、2−ブテニル、3−ブテニル、1,3−ブタジエニル、1−ヘキセニル等の炭素鎖の中に二重結合を有する直鎖または分岐状の炭素原子数が2〜6個のアルケニル基を表す。
「C2−C6アルキニル基」とは例えば、エチニル、プロパルギル、2−ペンチニル、1−ブチン−3−イル、1−ブチン−3−メチル−3−イル、3−ヘキシニル等の炭素鎖の中に三重結合を有する直鎖または分岐状の炭素原子数が2〜6個のアルキニル基を表す。
また、これらの置換基は、可能であればさらに置換基を有していてもよく、その置換基の具体例は上記と同様である。
また、本発明における一般式(3)等で表される化合物は、その構造式中に、炭素−炭素二重結合に由来する2種以上の幾何異性体が存在する場合もあるが、各々の幾何異性体が任意の割合で含まれる混合物をも全て包含する。
本発明の下記一般式(3)で表されるアミド誘導体の製造方法は、下記一般式(1)で表される化合物と、下記一般式(2)で表される化合物と、を反応させる工程を含む。かかる製造方法であることにより、有害生物防除作用に卓効を示すアミド誘導体を効率的に製造することができる。
LGで表される脱離基としては、ハロゲン原子、ヒドロキシ基、アリールオキシ基、アシルオキシ基等を挙げることができ、製造効率の観点から、ハロゲン原子、アリールオキシ基、アシルオキシ基であることが好ましく、ハロゲン原子であることがより好ましい。
例えば、一般式(2)で表される脱離基(LG)を有する芳香族カルボン酸誘導体と、一般式(1)で表される芳香族アミン誘導体とを適当な溶媒中もしくは無溶媒で反応させることにより、一般式(3)で表されるアミド誘導体を製造することができる。また本工程では適当な塩基を用いることもできる。
これらの塩基は、一般式(2)で表される化合物に対して0.01〜5倍モル当量の範囲で適宜選択して使用すれば良い。
反応温度は、−20℃〜使用する溶媒の還流温度、反応時間は、数分から96時間の範囲でそれぞれ適宜選択すれば良い。
ハロゲン化剤としては、例えば、塩化チオニル、臭化チオニル、シュウ酸ジクロリド、オキシ塩化リン、オキザリルクロリド、三塩化リン、五塩化リン等を示すことができる。
この反応は溶媒を用いてもよく、不活性な溶媒であればいずれのものでもよい。例えばジエチルエーテル、t−ブチルエチルエーテル、テトラヒドロフラン、ジオキサン、1,2−ジメトキシエタン等の鎖状または環状エーテル類、塩化メチレン、クロロホルム、四塩化炭素、ジクロロエタン、トリクロロエタン、ジクロロエチレン、クロロベンゼン、ジクロロベンゼン等のハロゲン化炭化水素類、ベンゼン、トルエン、キシレン、クロルベンゼン、ジクロロベンゼン等の芳香族炭化水素類、n−ヘキサン、ヘプタン、オクタン、シクロヘキサン等の脂肪族炭化水素類、酢酸エチル、酢酸ブチル等のエステル類、アセトニトリル、プロピオニトリル等のニトリル類、N,N−ジメチルホルムアミド、N,N−ジメチルアセトアミド、ジメチルスルホキシド、N−メチルピロリドン、1,3−ジメチル−2−イミダゾリジノン等の非プロトン性極性溶媒等から1種又は2種以上を適宜選択することができる。
反応は、通常−20〜140℃で行なうことができ、その反応時間は、通常0.1〜96時間から適宜選択される。
縮合剤を用いる方法、混合酸無水物法、活性エステル法共に、前記文献記載の溶媒、反応温度、反応時間に限定されることは無く、適宜反応の進行を著しく阻害しない不活性溶媒を使用すればよく、反応温度、反応時間についても、反応の進行に応じて、適宜選択すれば良い。
下記一般式(21)で表される化合物のうち、R3がC1−C6アルキル基、C3−C8シクロアルキル基、C2−C6アルケニル基、または、C2−C6アルキニル基である化合物を一般的な手法を利用した加水分解や、Pd触媒を用いた方法により、下記一般式(22)で表される化合物に変換することができる。具体的には、後述する一般式(8)で表される化合物から一般式(11)で表される化合物を製造する方法と同様にして、一般式(21)で表される化合物から一般式(22)で表される化合物を得ることができる。
LGで表される脱離基としては、ハロゲン原子、ヒドロキシ基、アリールオキシ基等を挙げることができ、製造効率の観点から、ハロゲン原子であることが好ましい。
さらに下記一般式(28)で表される化合物は、下記一般式(29)で表される化合物をアルキル化することで製造することができる。
LGで表される脱離基としては、ハロゲン原子、ヒドロキシ基、アリールオキシ基、アシルオキシ基等を挙げることができ、製造効率の観点から、ハロゲン原子、アリールオキシ基、アシルオキシ基であることが好ましく、ハロゲン原子であることがより好ましい。
使用する溶媒としては、本反応の進行を著しく阻害しないものであれば良く、例えば、ベンゼン、トルエン、キシレン等の芳香族炭化水素類、塩化メチレン、クロロホルム、四塩化炭素等のハロゲン化炭素類、、ジエチルエーテル、ジオキサン、テトラヒドロフラン、1,2−ジメトキシエタン等の鎖状または環状エーテル類、酢酸エチル、酢酸ブチル等のエステル類、アセトン、メチルイソブチルケトン、シクロヘキサノン等のケトン類、N,N−ジメチルホルムアミド、N,N−ジメチルアセトアミド、N−メチルピロリドン、ヘキサメチルホスホリックトリアミド、ジメチルスルホキシド、1,3−ジメチル−2−イミダゾリジノン等の極性非プロトン性溶媒類、アセトニトリル、プロピオニトリル等のニトリル類、水等を示すことができ、これらの溶媒を単独もしくは2種以上の溶媒を混合して使用できる。
これらの塩基は、一般式(5)で表される化合物に対して0.01〜5倍モル当量の範囲で適宜選択して使用すればよい。
反応温度は、−20℃から使用する溶媒の還流温度の範囲で適宜選択すればよい。また反応時間は、数分間から96時間の範囲で適宜選択すれば良い。
また一般式(7)で表される芳香族カルボン酸無水物は、芳香族カルボン酸を脱水剤の共存下、製造することができる。脱水剤として、塩化ホスホリル、無水酢酸、トリフルオロ酢酸無水物のような酸無水物あるいは酸塩化物、ハロギ酸エステル、カルボジイミド、等が例示できる
縮合剤を用いる方法、混合酸無水物を用いる方法共に前記文献記載の溶媒、反応温度、反応時間に限定されることは無い。溶媒としては、反応の進行を著しく阻害しない不活性溶媒を使用すればよく、反応温度、反応時間についても、反応の進行に応じて、適宜選択すればよい。
溶媒としては、本反応の進行を著しく阻害しないものであれば良く、例えば、n−ヘキサン、シクロヘキサン、メチルシクロヘキサン等の脂肪族炭化水素類、ベンゼン、トルエン、キシレン等の芳香族炭化水素類、塩化メチレン、クロロホルム、1,2−ジクロロエタン等のハロゲン化炭素類、ジエチルエーテル、ジオキサン、テトラヒドロフラン、1,2−ジメトキシエタン等の鎖状または環状エーテル類、酢酸エチル、酢酸ブチル等のエステル類、アセトン、メチルイソブチルケトン、シクロヘキサノン等のケトン類、N,N−ジメチルホルムアミド、N,N−ジメチルアセトアミド、N−メチルピロリドン、ヘキサメチルホスホリックトリアミド、ジメチルスルホキシド、1,3−ジメチル−2−イミダゾリジノン等の極性非プロトン性溶媒類、アセトニトリル、プロピオニトリル等のニトリル類、メタノール、エタノール等のアルコール類等を示すことができ、これらの溶媒を単独もしくは2種以上の溶媒を混合して使用できる。
これらの塩基は、一般式(13)で表される化合物に対して0.01から5倍モル等量の範囲で適宜選択、または溶媒として使用すればよい。
これらの反応剤は、一般式(13)で表される化合物に対して1から5倍モル等量の範囲で適宜選択、または溶媒として使用すればよい。
反応温度は、−80℃から使用する溶媒の還流温度、反応時間は数分間から96時間の範囲でそれぞれ適宜選択すればよい。
前記一般式(5)で表される化合物として、下記一般式(10)で表される化合物を用い、これを一般式(6)で表される化合物または一般式(7)で表される化合物と反応させることで、前記一般式(9)で表される化合物を製造することができる。
一般式(14)で表される化合物から、一般式(10)で表される化合物を製造する方法としては、以下の方法A〜方法Cを挙げることができる。
一般式(14)で表されるアミノ基を有する化合物を溶媒中、アルデヒド類またはケトン類と反応させ、触媒を添加し、水素雰囲気下で反応させることにより、一般式(10)で表されるアルキル化された化合物を製造することができる。
またケトン類としては、例えば、アセトン、パーフルオロアセトン、メチルエチルケトン等のケトン類を示すことができる。
一般式(14)で表される化合物を溶媒中で、アルデヒド類またはケトン類と反応させて、還元剤で処理することにより、一般式(10)で表される化合物を製造することができる。
ケトン類としては、例えば、アセトン、パーフルオロアセトン、メチルエチルケトン等のケトン類を示すことができる。
一般式(14)で表される化合物を溶媒中、または無溶媒でアルデヒド類と反応させることにより、一般式(10)で表される化合物を製造することができる。
一般式(8)で表される化合物のうち、R3がC1-C6アルキル基、C3-C8シクロアルキル基、C2-C6アルケニル基、または、C2-C6アルキニル基である化合物を、一般的な手法を利用した加水分解や、Pd触媒を用いた方法により、一般式(11)で表される化合物を得ることができる。例えば、加水分解による方法としては、メタノール、エタノールまたはテトラヒドロフラン、ジオキサンの単独または混合溶媒中、等量から5倍モルの水性またはアルコール性の水酸化リチウム、水酸化ナトリウムまたは水酸化カリウムを使用し塩基加水分解することにより得ることができる。またトルエン、キシレンなどの非水溶性溶媒中でも、水性の水酸化ナトリウム、水酸化カリウムまたは水酸化リチウムなどの塩基と、テトラブチルアンモニウムブロマイド、ベンジルトリエチルアンモニウムクロライドまたはクラウンエーテルなどの相間移動触媒との組み合わせによって加水分解を行うこともできる。また、塩酸や硫酸等の無機酸類、酢酸やトリフルオロ酢酸等の有機酸、強酸性樹脂を使用した酸加水分解を行うこともできる。
反応温度は、−20℃から使用する溶媒の還流温度の範囲で適宜選択すればよい。また反応時間は、数分から96時間の範囲で適宜選択すればよい。
また、Pdを用いる方法としては、例えば、Tetrahedron Letters 4371ページ(1987年)に記載されている方法を用いることができる。
一般式(12)で表される化合物は、一般式(11)で表される化合物を等モル以上のハロゲン化剤で処理することにより製造することができる。
ハロゲン化剤としては、例えば、塩化チオニル、臭化チオニル、シュウ酸ジクロリド、オキシ塩化リン、オキザリルクロリド、三塩化リン、五塩化リン等を示すことができる。
この反応は溶媒を用いてもよく、不活性な溶媒であればいずれのものでもよい。例えばジエチルエーテル、t−ブチルエチルエーテル、テトラヒドロフラン、ジオキサン、1,2−ジメトキシエタン等の鎖状または環状エーテル類、塩化メチレン、クロロホルム、四塩化炭素、ジクロロエタン、トリクロロエタン、ジクロロエチレン、クロロベンゼン、ジクロロベンゼン等のハロゲン化炭化水素類、ベンゼン、トルエン、キシレン、クロルベンゼン、ジクロロベンゼン等の芳香族炭化水素類、n−ヘキサン、ヘプタン、オクタン、シクロヘキサン等の脂肪族炭化水素類、酢酸エチル、酢酸ブチル等のエステル類、アセトニトリル、プロピオニトリル等のニトリル類、N,N−ジメチルホルムアミド、N,N−ジメチルアセトアミド、ジメチルスルホキシド、N−メチルピロリドン、1,3−ジメチル−2−イミダゾリジノン等の非プロトン性極性溶媒等から1種又は2種以上を適宜選択することができる。
反応は、通常−20〜140℃で行なうことができ、その反応時間は、通常0.1〜96時間から適宜選択される。
一般式(15)で表される化合物と、金属フッ化物、例えば、フッ化リチウム、フッ化ナトリウム、フッ化カリウム、フッ化セシウム、フッ化ルビジウム等よりなる群から選ばれる少なくとも1種または混合物とを、適当な溶媒中で反応させることにより一般式(16)で表される化合物を製造することができる。
金属フッ化物としては、フッ化ナトリウム、フッ化カリウム、フッ化セシウムが好ましい。金属フッ化物の形状、製法に特に制限はないが、スプレードライ品か、使用する前に加熱処理することが好ましく、使用前に加熱処理することが特に好ましい。加熱の温度は50℃〜250℃が好ましく、80℃〜200℃が特に好ましい。
金属フッ化物の量は、一般式(15)で表される化合物に対して、通常1モル以上用いるが、十分な収率で目的物を得るためには、1〜10モルが好ましく、1〜5モルが特に好ましい。
還元反応としては、水素添加反応を用いる方法と金属化合物(例えば、塩化第一スズ(無水物)、鉄粉、亜鉛粉等)を用いる方法を例示できる。前者は溶媒中、触媒存在下、常圧下もしくは加圧下にて、水素雰囲気下で反応を行うことができる。触媒としては、パラジウム/炭素等のパラジウム触媒、ラネーニッケル等のニッケル触媒、コバルト触媒、ルテニウム触媒、ロジウム触媒、白金触媒等が例示できる。例えば、パラジウム/炭素を、一般式(16)で表される化合物に対して金属重量1/10〜1/10,000倍を使用し、水素圧0.1〜10MPa、反応温度は通常0〜100℃で、数分〜96時間撹拌しながら行うことができる。溶媒として水やメタノール、エタノール等のアルコール類、エーテル、ジオキサン、テトラヒドロフラン等の鎖状または環状エーテル類、酢酸エチル、酢酸ブチル等のエステル類、N,N−ジメチルホルムアミド、1,3−ジメチル−2−イミダゾリジノン、ジメチルスルホキシド、スルホラン、N−メチルピロリドン、N,N−ジメチルアセトアミド等の非プロトン性極性溶媒を挙げることができ、これらを単独または混合して用いられる。
以下の第1表には、一般式(8)で表される化合物の代表的な例を示すが、本発明の化合物はこれらに限定されるものでない。なお、表中。「n−」はノルマルを、「i−」はイソを、「Me」はメチル基を、「Et」はエチル基を、「n−Pr」はノルマルプロピル基を、「n−Bu」はノルマルブチル基を、「n−Pn」はノルマルペンチル基を、「n−hex」はノルマルヘキシル基を、「i−Pr」はイソプロピル基を、「H」は水素原子を、「F」はフッ素原子を、「Cl」は塩素原子を、「CN」はニトリル基を、「Cyclo−Pr」はシクロプロピル基を、「Cyclo−hex」はシクロヘキシル基を、「CH2CH=CH2」はアリル基を、「CH2C≡CH」はプロパルギル基を、「CH2OCH3」はメトキシメチル基を、「CH2Ph」はベンジル基を、「CH2OCH2Ph」はベンジルオキシメチル基を、「C(CH3)3」はt−ブチル基を、「CH2CH2Cl」は2−クロロエチル基を、「NO2」はニトロ基を、それぞれ表すものである。
ヒラズハナアザミウマ(Frankliniella intonsa)、キイロハナアザミウマ(Thrips flavus)、ミカンキイロアザミウマ(Frankliniella occidentalis)、クロトンアザミウマ(Heliothrips haemorrhoidalis)、チャノキイロアザミウマ(Scirtothrips dorsalis)、ミナミキイロアザミウマ(Thrips palmi)、ネギアザミウマ(Thrips tabaci)、カキクダアザミウマ(Ponticulothrips diospyrosi)、等の総翅目昆虫、
クリハバチ(Apethymus kuri)、カブラハバチ(Athalia rosae)、チュウレンジハバチ(Arge pagana)、マツノキハバチ(Neodiprion sertifer)、クリタマバチ(Dryocosmus kuriphilus)、グンタイアリ(Eciton burchelli, Eciton schmitti)、クロオオアリ(Camponotus japonicus)、オオスズメバチ(Vespa mandarina)、ブルドックアント(Myrmecia spp.)、ファイヤーアント類(Solenopsis spp.)、ファラオアント(Monomorium pharaonis)等の膜翅目昆虫、
エンマコオロギ(Teleogryllus emma)、ケラ(Gryllotalpa orientalis)、トノサマバッタ(Locusta migratoria)、コバネイナゴ(Oxya yezoensis)、サバクワタリバッタ(Schistocerca gregaria)等の直翅目昆虫、
トゲナシシロトビムシ(Onychiurus folsomi)、シベリアシロトビムシ(Onychiurus sibiricus)、キボシマルトビムシ(Bourletiella hortensis)等の粘管目昆虫、
クロゴキブリ(Periplaneta fuliginosa)、ヤマトゴキブリ(Periplaneta japonica)、チャバネゴキブリ(Blattella germanica)、ワモンゴキブリ(Periplaneta Americana)、等の網翅目昆虫、
ネコノミ(Ctenocephalidae felis)、イヌノミ(Ctenocephalides canis)、ニワトリノミ(Echidnophaga gallinacea)、ヒトノミ(Pulex irritans)、ケオプスネズミノミ(Xenopsylla cheopis)等の等翅目昆虫、
ニワトリオオハジラミ(Menacanthus stramineus)、ウシハジラミ(Bovicola bovis)等のハジラミ目昆虫、
ウシジラミ(Haematopinus eurysternus)、ブタジラミ(Haematopinus suis)、ウシホソジラミ(Linognathus vituli)、ケブカウシジラミ(Solenopotes capillatus)等のシラミ目昆虫、
シクラメンホコリダニ(Phytonemus pallidus)、チャノホコリダニ(Polyphagotarsonemus latus)、スジブトホコリダニ(Tarsonemus bilobatus)等のホコリダニ類、
ハクサイダニ(Penthaleus erythrocephalus)、ムギダニ(Penthaleus major)等のハシリダニ類、
イネハダニ(Oligonychus shinkajii)、ミカンハダニ(Panonychus citri)、クワオオハダニ(Panonychus mori)、リンゴハダニ(Panonychus ulmi)、カンザワハダニ(Tetranychus kanzawai)、ナミハダニ(Tetranychus urticae)等のハダニ類、
チャノナガサビダニ(Acaphylla theavagrans)、チューリップサビダニ(Aceria tulipae)、トマトサビダニ(Aculops lycopersici)、ミカンサビダニ(Aculops pelekassi)、リンゴサビダニ(Aculus schlechtendali)、ニセナシサビダニ(Eriophyes chibaensis)、シトラスラストマイト(Phyllocoptruta oleivora)等のフシダニ類、
ロビンネダニ(Rhizoglyphus robini)、ケナガコナダニ(Tyrophagus putrescentiae)、ホウレンソウケナガコナダニ(Tyrophagus similis)等のコナダニ類、
ミツバチヘギイタダニ(Varroa jacobsoni)等のハチダニ類、
オウシマダニ(Boophilus microplus)、クリイロコイタマダニ(Rhipicephalus sanguineus)、フタトゲチマダニ(Haemaphysalis longicornis)、キチマダニ(Haemophysalis flava)、ツリガネチマダニ(Haemophysalis campanulata)、ヤマトマダニ(Ixodes ovatus)、シュルツェマダニ(Ixodes persulcatus)、オオマダニ(Amblyomma spp.)、アミメマダニ(Dermacentor spp.)等のマダニ類、
イヌツメダニ(Cheyletiella yasguri)、ネコツメダニ(Cheyletiella blakei)等のツメダニ類、イヌニキビダニ(Demodex canis)、ネコニキビダニ(Demodex cati)などのニキビダニ類、
ヒツジキュウセンダニ(Psoroptes ovis)等のキュウセンダニ類、
センコウヒゼンダニ(Sarcoptes scabiei)、ネコショウセンコウヒゼンダニ(Notoedres cati)、ニワトリヒゼンダニ(Knemidocoptes spp.)等のヒゼンダニ類、
オカダンゴムシ(Armadillidium vulgare)等の甲殻類、
スクミリンゴガイ(Pomacea canaliculata)、アフリカマイマイ(Achatina fulica)、ナメクジ(Meghimatium bilineatum)、チャコウラナメクジ(Limax Valentiana)、ウスカワマイマイ(Acusta despecta sieboldiana)、ミスジマイマイ(Euhadra peliomphala)等の腹足類、
ミナミネグサレセンチュウ(Prathylenchus coffeae)、キタネグサレセンチュウ(Prathylenchus penetrans)、クルミネグサレセンチュウ(Prathylenchus vulnus)、ジャガイモシストセンチュウ(Globodera rostochiensis)、ダイズシストセンチュウ(Heterodera glycines)、キタネコブセンチュウ(Meloidogyne hapla)、サツマイモネコブセンチュウ(Meloidogyne incognita)、イネシンガレセンチュウ(Aphelenchoides besseyi)、マツノザイセンチュウ(Bursaphelenchus xylophilus)等の線虫類、
等が挙げられるが、本発明における一般式(3)で表されるアミド誘導体を用いて防除しうる昆虫類、ダニ類、甲殻類、軟体動物及び線虫類はこれらのみに限定されるものではない。
さらに、本発明のアミド誘導体の製造方法を用いて製造した一般式(3)で表されるアミド誘導体は、他の農園芸用殺虫剤、殺ダニ剤、殺線虫剤、殺菌剤、除草剤、植物成長調節剤、生物農薬等と混合使用することによっても優れた防除効果を奏するものである。
使用できる不活性担体としては固体または液体のいずれであっても良く、固体の不活性担体になりうる材料としては、例えば、ダイズ粉、穀物粉、木粉、樹皮粉、鋸粉、タバコ茎粉、クルミ殻粉、ふすま、繊維素粉末、植物エキス抽出後の残渣、粉砕合成樹脂などの合成重合体、粘土類(例えばカオリン、ベントナイト、酸性白土など)、タルク類(例えばタルク、ピロフィライドなど)、シリカ類(例えば珪藻土、珪砂、雲母、ホワイトカーボン〔含水微粉珪素、含水珪酸ともいわれる合成高分散珪酸で、製品により珪酸カルシウムを主成分として含むものもある。〕)、活性炭、イオウ粉末、軽石、焼成珪藻土、レンガ粉砕物、フライアッシュ、砂、炭酸カルシウム、リン酸カルシウムなどの無機鉱物性粉末、硫安、燐安、硝安、尿素、塩安などの化学肥料、堆肥などを挙げることができ、これらは単独でもしくは二種以上の混合物の形で使用される。
これら界面活性剤の含有量は、特に限定されるものではないが、本発明の製剤100重量部に対し、通常0.05〜20重量部の範囲が望ましい。また、これら界面活性剤は、単独で用いても2種以上を併用してもよい。
また、本発明化合物を農薬として使用する場合には、必要に応じて製剤時又は散布時に他種の除草剤、各種殺虫剤、殺ダニ剤、殺線虫剤、殺菌剤、植物生長調節剤、共力剤、肥料、土壌改良剤等と混合施用してもよい。
本明細書に記載された全ての文献、特許出願、および技術規格は、個々の文献、特許出願、および技術規格が参照により取り込まれることが具体的かつ個々に記された場合と同程度に、本明細書に参照により取り込まれる。
2−フルオロ−3−(N−メチルベンズアミド)安息香酸メチルの製造(化合物番号1−2)
(工程1)
2−クロロ−3−ニトロ安息香酸メチルの製造
1H−NMR(CDCl3,ppm)δ3.98(3H,s),7.46−7.50(1H,m),7.83−7.86(1H,m),7.94−7.98(1H,m).
(工程2)
2−フルオロ−3−ニトロ安息香酸メチルの製造
1H−NMR(CDCl3,ppm)δ3.99(3H,s),7.36−7.40(1H,m),8.14−8.25(2H,m).
(工程3)
3−アミノ−2−フルオロ安息香酸メチル塩酸塩の製造
1H−NMR(DMSO-d6,ppm)δ3.86(3H,s),7.21−7.25(1H,m),7.27(3H,brs),7.42−7.53(2H,m).
(工程4)
3−ベンズアミド−2−フルオロ安息香酸メチルの製造(化合物番号1−1)
1H−NMR(CDCl3,ppm)δ3.95(3H,s),7.24−7.28(1H,m),7.51−7.58(3H,m),7.66−7.70(1H,m),7.89−7.91(2H,m),8.20−8.22(1H,m),8.70−8.73(1H,m).
(工程5)
2−フルオロ−3−(N−メチルベンズアミド)安息香酸メチルの合成(化合物番号1−2)
1H−NMR(CDCl3,ppm)δ3.43(3H,s),3.90(3H,s),7.01−7.05(1H,m),7.20−7.33(6H,m),7.77−7.79(1H,m)
2−フルオロ−3−(N−メチルベンズアミド)安息香酸クロリドの製造(化合物番号2−5)
(工程1)
2−フルオロ−3−(メチルアミノ)安息香酸メチルの合成
1H−NMR(CDCl3,ppm)δ2.89(3H,s),3.91(3H,s),6.80−6.85(1H,m),7.03−7.09(1H,m),7.14−7.16(2H,m).
(工程2)
2−フルオロ−3−(N−メチルベンズアミド)安息香酸メチルの合成(化合物番号1−2)
1H−NMR(CDCl3,ppm)δ3.43(3H,s),3.92(3H,s),7.01−7.05(1H,m),7.19−7.32(6H,m),7.76−7.79(1H,m)
(工程3)
2−フルオロ−3−(N−メチルベンズアミド)安息香酸の合成(化合物番号1−3)
1H−NMR(CDCl3,ppm)δ3.45(3H,s),7.05−7.09(1H,m),7.21−7.35(6H,m),7.85−7.90(1H,m),10.29(1H,brs)
(工程4)
2−フルオロ−3−(N−メチルベンズアミド)安息香酸クロリドの製造(化合物番号2−5)
1H−NMR(CDCl3,ppm)δ3.17(3H,s),7.15(1H,t,J=8.0Hz),7.23−7.35(6H,m),7.94(1H,t,J=8.0Hz).
2−フルオロ−3−(4−フルオロ−N−メチルベンズアミド)安息香酸クロリドの製造(化合物番号2−15)
(工程1)
2−フルオロ−3−(4−フルオロベンズアミド)安息香酸メチルの製造(化合物番号1−20)
1H−NMR(CDCl3,ppm)δ3.95(3H,s), 7.17−7.27(3H, m), 7.66−7.70(1H,m), 7.89−7.94(2H,m), 8.11(1H,brs), 8.63−8.68(1H,m)
(工程2)
2−フルオロ−3−(4−フルオロ−N−メチルベンズアミド)安息香酸メチルの製造(化合物番号1−21)
1H−NMR(CDCl3,ppm)δ3.42(3H,s),3.88(3H,s),6.86−6.90(2H,m),7.09−7.13(1H,m),7.32−7.38(3H,m),7.78−7.82(1H,m).
(工程3)
2−フルオロ−3−(4−フルオロ−N−メチルベンズアミド)安息香酸の製造(化合物番号1−22)
1H−NMR(CDCl3,ppm)δ3.45(3H,s), 6.87−6.91(2H, m), 7.10-7.18(1H,m), 7.30−7.37(3H, m), 7.87−7.92(1H,m) カルボン酸のプロトン検出されず。
2−フルオロ−3−(4−フルオロ−N−メチルベンズアミド)安息香酸クロリドの製造(化合物番号2−15)
1H−NMR(CDCl3,ppm)δ2.95(3H,s), 6.92(2H, t,J=8.8Hz), 7.19(1H,t,J=8.0Hz), 7.33−7.36(3H, m), 7.97(1H,t,J=8.0Hz)
2−フルオロ−3−(3−フルオロ−N−メチルベンズアミド)安息香酸の製造(化合物番号1−65)
(工程1)
2−フルオロ−3−(3−フルオロベンズアミド)安息香酸メチルの製造(化合物番号1−63)
1H−NMR(CDCl3,ppm)δ3.95(3H,s),7.24−7.30(2H,s),7.48−7.54(1H,m),7.61−7.72(3H,m),8.10(1H,brs),8.68−8.70(1H,m)
(工程2)
2−フルオロ−3−(3−フルオロ−N−メチルベンズアミド)安息香酸メチルの製造(化合物番号1−64)
1H−NMR(CDCl3,ppm)δ3.46(3H,s),3.93(3H,s),6.95−7.22(6H,m),7.79−7.82(1H,m)
(工程3)
2−フルオロ−3−(3−フルオロ−N−メチルベンズアミド)安息香酸の製造(化合物番号1−65)
1H−NMR(CDCl3,ppm)δ3.44(3H,s),6.98−7.00(1H,m),7.07−7.16(4H,m),7.29−7.30(1H,m),7.88−7.91(1H,m),カルボン酸のプロトン観測されず。
3−(N−エチルベンズアミド)−2−フルオロ安息香酸の製造(化合物番号1−11)
(工程1)
3−(N−エチルベンズアミド)−2−フルオロ安息香酸メチルの製造(化合物番号1−10)
1H−NMR(CDCl3,ppm)δ1.19−1.28(3H,m),3.88−4.04(5H,m),7.06−7.30(7H,m),7.80−7.83(1H,m).
(工程2)
3−(N−エチルベンズアミド)−2−フルオロ安息香酸の製造(化合物番号1−11)
1H−NMR(DMSO−d6,ppm)δ1.08−1.19(3H,m),3.74−3.89(2H,m),7.24−7.40(6H,m),7.64−7.73(2H,m),13.36(1H,brs)
2−フルオロ−3−(N−n−プロピルベンズアミド)安息香酸の製造(化合物番号1−13)
(工程1)
2−フルオロ−3−(N−n−プロピルベンズアミド)安息香酸メチルの製造(化合物番号1−12)
1H−NMR(CDCl3,ppm)δ0.92−1.02(3H,m)、1.59−1.63(2H,m)、3.72−3.78(2H,m)、3.09(3H,s)、7.05−7.06(1H,m),7.18−7.28(6H,m)、7.70−7.71(1H,m)
(工程2)
2−フルオロ−3−(N−n−プロピルベンズアミド)安息香酸の製造(化合物番号1−13)
1H−NMR(CDCl3+DMSO−d6,ppm)δ0.88−0.94(3H,m),1.60−1.65(2H,m),3.72−3.73(1H,m),3.91−3.92(1H,m),7.04−7.06(1H,m)、7.22−7.28(6H,m)、7.79−7.80(1H,m)カルボン酸のプロトン検出されず
3−(2−クロロ−4−フルオロ−N−メチルベンズアミド)−2−フルオロ安息香酸の製造(化合物番号1−139)
(工程1)
3−(2−クロロ−4−フルオロベンズアミド)−2−フルオロ安息香酸メチルの製造(化合物番号1−137)
1H−NMR(CDCl3,ppm)δ3.95(3H,s),7.11−7.16(1H,m),7.22−7.28(2H,m),7.68−7.72(1H,m),7.89−7.92(1H,m),8.45(1H,brs),8.69(1H,t,J=7.8Hz)
(工程2)
3−(2−クロロ−4−フルオロ−N−メチルベンズアミド)−2−フルオロ安息香酸メチルの製造(化合物番号1−138)
1H−NMR(CDCl3,ppm)δ3.44(3H,s),3.92(3H,s),6.80−6.84(1H,m),6.93(1H,dd,J=2.0,7.3Hz),7.04(1H,t,J=7.8Hz),7.21−7.25(1H,m),7.37(1H,t,J=7.3Hz),7.76−7.80(1H,m).
(工程3)
3−(2−クロロ−4−フルオロ−N−メチルベンズアミド)−2−フルオロ安息香酸の製造(化合物番号1−139)
1H−NMR(CDCl3,ppm)δ3.46(3H,s),5.70(1H,brs),6.82−6.86(1H,m),6.94(1H,dd,J=2.4,8.8Hz),7.08(1H,t,J=7.8Hz),7.22−7.28(1H,m),7.47−7.48(1H,m)、7.84−7.88(1H,m).
3−(4−シアノ−N−メチルベンズアミド)−2−フルオロ安息香酸の製造(化合物番号1−104)
(工程1)
3−(4−シアノベンズアミド)−2−フルオロ安息香酸メチルの製造(化合物番号1−102)
1H−NMR(DMSO−d6,ppm)δ3.88(3H,s),7.36(1H,t,J=7.8Hz),7.75−7.79(1H,m),7.87−7.91(1H,m),8.03−8.10(2H,m),8.13−8.15(2H,m),10.53(1H,s).
(工程2)
3−(4−シアノ−N−メチルベンズアミド)−2−フルオロ安息香酸メチルの製造(化合物番号1−103)
1H−NMR(CDCl3,ppm)δ3.44(3H,s),3.92(3H,s),7.08−7.12(1H,m),7.25(1H,brs),7.41−7.43(2H,m),7.49−7.51(2H,m),7.81−7.84(1H,s).
(工程3)
3−(4−シアノ−N−メチルベンズアミド)−2−フルオロ安息香酸の製造(化合物番号1−104)
1H−NMR(DMSO−d6,ppm)δ3.33(3H,s),7.22(1H,brs),7.45(2H,brs),7.69−7.74(4H,brs).カルボン酸のプロトン検出されず。
N−(2−ブロモ−4−(パーフルオロプロパン−2−イル)−6−(トリフルオロメチル)フェニル)−2−フルオロ−3−(N−メチルベンズアミド)ベンズアミドの製造(化合物番号3−1)
1H−NMR(CDCl3,ppm)δ3.50(3H,s),6.99−7.33(6H,m),7.43−7.45(1H,m),7.90(1H,s),7.97−8.06(2H,m),8.13(1H,s).
実施例9記載の方法に従って、2−フルオロ−3−(N−メチルベンズアミド)安息香酸と2−ブロモ−4−(パーフルオロプロパン−2−イル)−6−(トリフルオロメチル)アニリンの反応を、1,3−ジメチル−2−イミダゾリジノンの代わりにトルエンを用いて行ったところ、収率14%で実施例9の標記化合物を得た。
実施例9記載の方法に従って、2−フルオロ−3−(N−メチルベンズアミド)安息香酸と2−ブロモ−4−(パーフルオロプロパン−2−イル)−6−(トリフルオロメチル)アニリンの反応を、1,3−ジメチル−2−イミダゾリジノンの代わりにジオキサンを用いて行ったところ、収率16%で実施例9の標記化合物を得た。
実施例9記載の方法に従って、2−フルオロ−3−(N−メチルベンズアミド)安息香酸と2−ブロモ−4−(パーフルオロプロパン−2−イル)−6−(トリフルオロメチル)アニリンの反応を、1,3−ジメチル−2−イミダゾリジノンを用いずに無溶媒で行ったところ、収率37%で実施例9の標記化合物を得た。
実施例9において、2−フルオロ−3−(N−メチルベンズアミド)安息香酸(一般式(2)で表される化合物)、および、2−ブロモ−4−(パーフルオロプロパン−2−イル)−6−(トリフルオロメチル)アニリン(一般式(1)で表される化合物)の代わりに、下記第4表に示した化合物をそれぞれ用いたこと以外は実施例9と同様にして、対応する一般式(3)で表されるアミド誘導体を得た。
<製剤例1>
一般式(3)で表されるアミド誘導体20部、ポリオキシエチレンスチリルフェニルエーテル10部、キシレン70部、以上を均一に混合して乳剤を得た。
<製剤例2>
一般式(3)で表されるアミド誘導体10部、ラウリル硫酸ナトリウム2部、ジアルキルスルホサクシネート2部、β‐ナフタレンスルホン酸ホルマリン縮合物ナトリウム塩1部、珪藻土85部以上を均一に攪拌混合して水和剤を得た。
<製剤例3>
一般式(3)で表されるアミド誘導体0.3部、ホワイトカーボン0.3部を均一に混合し、クレー99.2部、ドリレスA(三共アグロ製)0.2部を加えて、均一に粉砕混合し、粉剤を得た。
<製剤例4>
一般式(3)で表されるアミド誘導体3部、ポリオキシエチレン・ポリオキシプロピレン縮合物1.5部、カルボキシメチルセルロース3部、クレー64.8部、タルク27.7部、以上を均一に粉砕混合後、水を加えて混練し、造粒乾燥して粒剤を得た。
<製剤例5>
一般式(3)で表されるアミド誘導体10部、β‐ナフタレンスルホン酸ホルマリン縮合物ナトリウム塩3部、トリスチリルフェノール1部、プロピレングリコール5部、シリコン系消泡剤0.5部、水33.5部を十分攪拌混合した後、キサンタンガム0.3部、水46.7部を混合したものと再び攪拌混合してフロアブル剤を得た。
<製剤例6>
一般式(3)で表されるアミド誘導体20部、ナフタレンスルホン酸ホルムアルデヒド縮合物金属塩6部、ジアルキルスルホコハク酸金属塩1部、炭酸カルシウム73部、以上を均一に粉砕混合後、水を加えて混練し、造粒乾燥して顆粒水和剤を得た。
<試験例1>
ハスモンヨトウ(Spodoptera litura)に対する殺虫試験
試験化合物を所定濃度に調製した薬液にキャベツ葉片を30秒間浸漬し風乾後、ろ紙を敷いた7cmのポリエチレンカップに入れハスモンヨトウ2齢幼虫を放虫した。25℃恒温室にて放置し、6日後に生死虫数を調査した。1区5頭2連制で行った。
上記試験の結果、本製造方法を利用して製造した実施例9、実施例13〜19で得られた一般式(3)で表されるアミド誘導体はいずれも、濃度1ppmで70%以上の死虫率を示した。
コナガ(Plutella xylostella)に対する殺虫試験
試験化合物を所定濃度に調製した薬液にキャベツ葉片を30秒間浸漬し風乾後、ろ紙を敷いた7cmのポリエチレンカップに入れコナガ3齢幼虫を放虫した。25℃恒温室にて放置し、6日後に生死虫数を調査した。1区5頭2連制で行った。
上記試験の結果、本製造方法を利用して製造した実施例9、実施例13〜19で得られた一般式(3)で表されるアミド誘導体はいずれも、濃度1ppmで70%以上の死虫率を示した。
Claims (2)
- 下記一般式(8)
(一般式(8)中、R2は水素原子、メチル基、エチル基、またはn−プロピル基を表し、R3は水素原子またはメチル基を表し、X1は水素原子または塩素原子を表し、X2は水素原子またはフッ素原子を表し、X3 は水素原子、フッ素原子、またはニトリル基を表し、X4およびX5は水素原子を表す。)で表される化合物において、R3が水素原子を表す場合には、前記一般式(8)で表される化合物をハロゲン化剤で処理することにより製造される下記一般式(12)
(一般式(12)中、R2は水素原子、メチル基、エチル基、またはn−プロピル基を表し、Halは塩素原子を表し、X1は水素原子または塩素原子を表し、X2は水素原子またはフッ素原子を表し、X3 は水素原子、フッ素原子、またはニトリル基を表し、X4およびX5は水素原子を表す。)で表される化合物、又はR3がメチル基を表す場合には、前記一般式(8)で表される化合物より製造される下記一般式(11)
(一般式(11)中、R2は水素原子、メチル基、エチル基、またはn−プロピル基を表し、X1は水素原子または塩素原子を表し、X2は水素原子またはフッ素原子を表し、X3 は水素原子、フッ素原子、またはニトリル基を表し、X4およびX5は水素原子を表す。)で表される化合物をさらにハロゲン化剤で処理することにより得られる前記一般式(12)で表される化合物と、下記一般式(1)
(一般式(1)中、Y1およびY2はそれぞれ独立に、ハロゲン原子またはC1−C3ハロアルキル基を表し、RfはC3−C4パーフルオロアルキル基を表し、R1は水素原子またはC1−C4アルキル基を表す。)で表される化合物と、を反応させることにより下記一般式(4)
(一般式(4)中、X1は水素原子または塩素原子を表し、X2は水素原子またはフッ素原子を表し、X3 は水素原子、フッ素原子、またはニトリル基を表し、X4およびX5は水素原子を表し、R1は、水素原子またはC1−C4アルキル基を表し、R2は、水素原子、メチル基、エチル基、またはn−プロピル基を表し、Y1およびY2はそれぞれ独立に、ハロゲン原子またはC1−C3ハロアルキル基を表し、Rfは、C3−C4パーフルオロアルキル基を表す。)で表される化合物を製造する製造方法に用いられる前記一般式(8)で表される化合物である、一般式(1)で表される化合物用のアシル化剤。 - 下記一般式(1)
(一般式(1)中、Y1およびY2はそれぞれ独立に、ハロゲン原子またはC1−C3ハロアルキル基を表し、RfはC3−C4パーフルオロアルキル基を表し、R1は水素原子またはC1−C4アルキル基を表す。)で表される化合物と反応させることによって製造される下記一般式(4)
(一般式(4)中、X1は水素原子または塩素原子を表し、X2は水素原子またはフッ素原子を表し、X3 は水素原子、フッ素原子、またはニトリル基を表し、X4およびX5は水素原子を表し、R1は、水素原子またはC1−C4アルキル基を表し、R2は、水素原子
、メチル基、エチル基、またはn−プロピル基を表し、Y1およびY2はそれぞれ独立に、ハロゲン原子またはC1−C3ハロアルキル基を表し、Rfは、C3−C4パーフルオロアルキル基を表す。)で表される化合物の製造中間体として用いられる下記一般式(12)
(一般式(12)中、R2は水素原子、メチル基、エチル基、またはn−プロピル基を表し、Halは塩素原子を表し、X1は水素原子または塩素原子を表し、X2は水素原子またはフッ素原子を表し、X3 は水素原子、フッ素原子、またはニトリル基を表し、X4およびX5は水素原子を表す。)で表される化合物である、一般式(1)で表される化合物用のアシル化剤。
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