JP7422772B2 - 除草性置換n-テトラゾリルアリールカルボキサミド - Google Patents
除草性置換n-テトラゾリルアリールカルボキサミド Download PDFInfo
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- JP7422772B2 JP7422772B2 JP2021540558A JP2021540558A JP7422772B2 JP 7422772 B2 JP7422772 B2 JP 7422772B2 JP 2021540558 A JP2021540558 A JP 2021540558A JP 2021540558 A JP2021540558 A JP 2021540558A JP 7422772 B2 JP7422772 B2 JP 7422772B2
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- YXIIPOGUBVYZIW-UHFFFAOYSA-N pyraflufen Chemical compound ClC1=C(OC(F)F)N(C)N=C1C1=CC(OCC(O)=O)=C(Cl)C=C1F YXIIPOGUBVYZIW-UHFFFAOYSA-N 0.000 description 1
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- ASRAWSBMDXVNLX-UHFFFAOYSA-N pyrazolynate Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1OS(=O)(=O)C1=CC=C(C)C=C1 ASRAWSBMDXVNLX-UHFFFAOYSA-N 0.000 description 1
- VTRWMTJQBQJKQH-UHFFFAOYSA-N pyributicarb Chemical compound COC1=CC=CC(N(C)C(=S)OC=2C=C(C=CC=2)C(C)(C)C)=N1 VTRWMTJQBQJKQH-UHFFFAOYSA-N 0.000 description 1
- DEIKMOQTJBGGAX-DJKKODMXSA-N pyriminobac Chemical compound CO\N=C(/C)C1=CC=CC(OC=2N=C(OC)C=C(OC)N=2)=C1C(O)=O DEIKMOQTJBGGAX-DJKKODMXSA-N 0.000 description 1
- USSIUIGPBLPCDF-KEBDBYFISA-N pyriminobac-methyl Chemical group CO\N=C(/C)C1=CC=CC(OC=2N=C(OC)C=C(OC)N=2)=C1C(=O)OC USSIUIGPBLPCDF-KEBDBYFISA-N 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- FFSSWMQPCJRCRV-UHFFFAOYSA-N quinclorac Chemical compound ClC1=CN=C2C(C(=O)O)=C(Cl)C=CC2=C1 FFSSWMQPCJRCRV-UHFFFAOYSA-N 0.000 description 1
- ALZOLUNSQWINIR-UHFFFAOYSA-N quinmerac Chemical compound OC(=O)C1=C(Cl)C=CC2=CC(C)=CN=C21 ALZOLUNSQWINIR-UHFFFAOYSA-N 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- FFRYUAVNPBUEIC-UHFFFAOYSA-N quinoxalin-2-ol Chemical class C1=CC=CC2=NC(O)=CN=C21 FFRYUAVNPBUEIC-UHFFFAOYSA-N 0.000 description 1
- ABOOPXYCKNFDNJ-SNVBAGLBSA-N quizalofop-P Chemical compound C1=CC(O[C@H](C)C(O)=O)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 ABOOPXYCKNFDNJ-SNVBAGLBSA-N 0.000 description 1
- OSUHJPCHFDQAIT-GFCCVEGCSA-N quizalofop-P-ethyl Chemical group C1=CC(O[C@H](C)C(=O)OCC)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 OSUHJPCHFDQAIT-GFCCVEGCSA-N 0.000 description 1
- BBKDWPHJZANJGB-IKJXHCRLSA-N quizalofop-P-tefuryl Chemical group O=C([C@H](OC=1C=CC(OC=2N=C3C=CC(Cl)=CC3=NC=2)=CC=1)C)OCC1CCCO1 BBKDWPHJZANJGB-IKJXHCRLSA-N 0.000 description 1
- BACHBFVBHLGWSL-JTQLQIEISA-N rac-diclofop methyl Natural products C1=CC(O[C@@H](C)C(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1Cl BACHBFVBHLGWSL-JTQLQIEISA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 238000010188 recombinant method Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 230000001850 reproductive effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 229940043267 rhodamine b Drugs 0.000 description 1
- 239000003161 ribonuclease inhibitor Substances 0.000 description 1
- 108091092562 ribozyme Proteins 0.000 description 1
- MEFOUWRMVYJCQC-UHFFFAOYSA-N rimsulfuron Chemical compound CCS(=O)(=O)C1=CC=CN=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 MEFOUWRMVYJCQC-UHFFFAOYSA-N 0.000 description 1
- 230000005070 ripening Effects 0.000 description 1
- 230000002786 root growth Effects 0.000 description 1
- GNHDVXLWBQYPJE-UHFFFAOYSA-N saflufenacil Chemical compound C1=C(Cl)C(C(=O)NS(=O)(=O)N(C)C(C)C)=CC(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C1F GNHDVXLWBQYPJE-UHFFFAOYSA-N 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229930000044 secondary metabolite Natural products 0.000 description 1
- 230000007226 seed germination Effects 0.000 description 1
- 239000003620 semiochemical Substances 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
- XMVONEAAOPAGAO-UHFFFAOYSA-N sodium tungstate Chemical compound [Na+].[Na+].[O-][W]([O-])(=O)=O XMVONEAAOPAGAO-UHFFFAOYSA-N 0.000 description 1
- JKPSVOHVUGMYGH-UHFFFAOYSA-M sodium;(4,6-dimethoxypyrimidin-2-yl)-[[3-methoxycarbonyl-6-(trifluoromethyl)pyridin-2-yl]sulfonylcarbamoyl]azanide Chemical compound [Na+].COC(=O)C1=CC=C(C(F)(F)F)N=C1S(=O)(=O)NC(=O)[N-]C1=NC(OC)=CC(OC)=N1 JKPSVOHVUGMYGH-UHFFFAOYSA-M 0.000 description 1
- KZOJQMWTKJDSQJ-UHFFFAOYSA-M sodium;2,3-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 KZOJQMWTKJDSQJ-UHFFFAOYSA-M 0.000 description 1
- STAPBGVGYWCRTF-UHFFFAOYSA-M sodium;2-(4-chloro-2-methylphenoxy)acetate Chemical compound [Na+].CC1=CC(Cl)=CC=C1OCC([O-])=O STAPBGVGYWCRTF-UHFFFAOYSA-M 0.000 description 1
- DHJHUXNTNSRSEX-UHFFFAOYSA-M sodium;2-(4-chloro-2-methylphenoxy)propanoate Chemical compound [Na+].[O-]C(=O)C(C)OC1=CC=C(Cl)C=C1C DHJHUXNTNSRSEX-UHFFFAOYSA-M 0.000 description 1
- YWICANUUQPYHOW-UHFFFAOYSA-M sodium;2-(phosphonomethylamino)acetate Chemical compound [Na+].OP(O)(=O)CNCC([O-])=O YWICANUUQPYHOW-UHFFFAOYSA-M 0.000 description 1
- JUNDBKFAZXZKRA-MAFYXNADSA-M sodium;2-[(e)-n-[(3,5-difluorophenyl)carbamoylamino]-c-methylcarbonimidoyl]pyridine-3-carboxylate Chemical compound [Na+].N=1C=CC=C(C([O-])=O)C=1C(/C)=N/NC(=O)NC1=CC(F)=CC(F)=C1 JUNDBKFAZXZKRA-MAFYXNADSA-M 0.000 description 1
- PPKIJAQKBAYNNL-UHFFFAOYSA-M sodium;4-(2,4-dichlorophenoxy)butanoate Chemical compound [Na+].[O-]C(=O)CCCOC1=CC=C(Cl)C=C1Cl PPKIJAQKBAYNNL-UHFFFAOYSA-M 0.000 description 1
- GABUSZPTCJGKGB-UHFFFAOYSA-M sodium;4-(4-chloro-2-methylphenoxy)butanoate Chemical compound [Na+].CC1=CC(Cl)=CC=C1OCCCC([O-])=O GABUSZPTCJGKGB-UHFFFAOYSA-M 0.000 description 1
- JRQGDDUXDKCWRF-UHFFFAOYSA-M sodium;n-(2-methoxycarbonylphenyl)sulfonyl-4-methyl-5-oxo-3-propoxy-1,2,4-triazole-1-carboximidate Chemical compound [Na+].O=C1N(C)C(OCCC)=NN1C(=O)[N-]S(=O)(=O)C1=CC=CC=C1C(=O)OC JRQGDDUXDKCWRF-UHFFFAOYSA-M 0.000 description 1
- 239000004550 soluble concentrate Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 235000021012 strawberries Nutrition 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- PQTBTIFWAXVEPB-UHFFFAOYSA-N sulcotrione Chemical compound ClC1=CC(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O PQTBTIFWAXVEPB-UHFFFAOYSA-N 0.000 description 1
- OORLZFUTLGXMEF-UHFFFAOYSA-N sulfentrazone Chemical compound O=C1N(C(F)F)C(C)=NN1C1=CC(NS(C)(=O)=O)=C(Cl)C=C1Cl OORLZFUTLGXMEF-UHFFFAOYSA-N 0.000 description 1
- FZMKKCQHDROFNI-UHFFFAOYSA-N sulfometuron Chemical compound CC1=CC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 FZMKKCQHDROFNI-UHFFFAOYSA-N 0.000 description 1
- ZDXMLEQEMNLCQG-UHFFFAOYSA-N sulfometuron methyl Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=CC(C)=N1 ZDXMLEQEMNLCQG-UHFFFAOYSA-N 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000004546 suspension concentrate Substances 0.000 description 1
- 239000004548 suspo-emulsion Substances 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical class NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 1
- IUQAXCIUEPFPSF-UHFFFAOYSA-N tembotrione Chemical compound ClC1=C(COCC(F)(F)F)C(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O IUQAXCIUEPFPSF-UHFFFAOYSA-N 0.000 description 1
- IROINLKCQGIITA-UHFFFAOYSA-N terbutryn Chemical compound CCNC1=NC(NC(C)(C)C)=NC(SC)=N1 IROINLKCQGIITA-UHFFFAOYSA-N 0.000 description 1
- FZXISNSWEXTPMF-UHFFFAOYSA-N terbutylazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C)=N1 FZXISNSWEXTPMF-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- GLDAZAQRGCSFNP-UHFFFAOYSA-N thiencarbazone Chemical compound O=C1N(C)C(OC)=NN1C(=O)NS(=O)(=O)C1=C(C)SC=C1C(O)=O GLDAZAQRGCSFNP-UHFFFAOYSA-N 0.000 description 1
- XSKZXGDFSCCXQX-UHFFFAOYSA-N thiencarbazone-methyl Chemical group COC(=O)C1=CSC(C)=C1S(=O)(=O)NC(=O)N1C(=O)N(C)C(OC)=N1 XSKZXGDFSCCXQX-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- LOQQVLXUKHKNIA-UHFFFAOYSA-N thifensulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C2=C(SC=C2)C(O)=O)=N1 LOQQVLXUKHKNIA-UHFFFAOYSA-N 0.000 description 1
- AHTPATJNIAFOLR-UHFFFAOYSA-N thifensulfuron-methyl Chemical group S1C=CC(S(=O)(=O)NC(=O)NC=2N=C(OC)N=C(C)N=2)=C1C(=O)OC AHTPATJNIAFOLR-UHFFFAOYSA-N 0.000 description 1
- 230000009974 thixotropic effect Effects 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- IYMLUHWAJFXAQP-UHFFFAOYSA-N topramezone Chemical compound CC1=C(C(=O)C2=C(N(C)N=C2)O)C=CC(S(C)(=O)=O)=C1C1=NOCC1 IYMLUHWAJFXAQP-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- DQFPEYARZIQXRM-LTGZKZEYSA-N tralkoxydim Chemical compound C1C(=O)C(C(/CC)=N/OCC)=C(O)CC1C1=C(C)C=C(C)C=C1C DQFPEYARZIQXRM-LTGZKZEYSA-N 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- XOPFESVZMSQIKC-UHFFFAOYSA-N triasulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OCCCl)=N1 XOPFESVZMSQIKC-UHFFFAOYSA-N 0.000 description 1
- BQZXUHDXIARLEO-UHFFFAOYSA-N tribenuron Chemical compound COC1=NC(C)=NC(N(C)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 BQZXUHDXIARLEO-UHFFFAOYSA-N 0.000 description 1
- YMXOXAPKZDWXLY-QWRGUYRKSA-N tribenuron methyl Chemical group COC(=O)[C@H]1CCCC[C@@H]1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 YMXOXAPKZDWXLY-QWRGUYRKSA-N 0.000 description 1
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- AZHZOGYUMMIAOF-UHFFFAOYSA-N trifludimoxazin Chemical compound O=C1N(C)C(=S)N(C)C(=O)N1C(C(=C1)F)=CC2=C1OC(F)(F)C(=O)N2CC#C AZHZOGYUMMIAOF-UHFFFAOYSA-N 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- AKTQJCBOGPBERP-UHFFFAOYSA-N triflusulfuron Chemical compound FC(F)(F)COC1=NC(N(C)C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2C)C(O)=O)=N1 AKTQJCBOGPBERP-UHFFFAOYSA-N 0.000 description 1
- IMEVJVISCHQJRM-UHFFFAOYSA-N triflusulfuron-methyl Chemical group COC(=O)C1=CC=CC(C)=C1S(=O)(=O)NC(=O)NC1=NC(OCC(F)(F)F)=NC(N(C)C)=N1 IMEVJVISCHQJRM-UHFFFAOYSA-N 0.000 description 1
- DFFWZNDCNBOKDI-UHFFFAOYSA-N trinexapac Chemical compound O=C1CC(C(=O)O)CC(=O)C1=C(O)C1CC1 DFFWZNDCNBOKDI-UHFFFAOYSA-N 0.000 description 1
- RVKCCVTVZORVGD-UHFFFAOYSA-N trinexapac-ethyl Chemical group O=C1CC(C(=O)OCC)CC(=O)C1=C(O)C1CC1 RVKCCVTVZORVGD-UHFFFAOYSA-N 0.000 description 1
- KVEQCVKVIFQSGC-UHFFFAOYSA-N tritosulfuron Chemical compound FC(F)(F)C1=NC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(F)(F)F)=N1 KVEQCVKVIFQSGC-UHFFFAOYSA-N 0.000 description 1
- 230000001228 trophic effect Effects 0.000 description 1
- YNWVFADWVLCOPU-MAUPQMMJSA-N uniconazole P Chemical compound C1=NC=NN1/C([C@@H](O)C(C)(C)C)=C/C1=CC=C(Cl)C=C1 YNWVFADWVLCOPU-MAUPQMMJSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 239000012873 virucide Substances 0.000 description 1
- 238000009369 viticulture Methods 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
- C07D257/06—Five-membered rings with nitrogen atoms directly attached to the ring carbon atom
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/32—Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P13/00—Herbicides; Algicides
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- General Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Dentistry (AREA)
- Agronomy & Crop Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Toxicology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
RXは、(C1~C6)-アルキルまたは(C1~C6)-アルキル-O-(C1~C6)-アルキルであり、
Xは、ハロゲン、(C1~C6)-アルキル、ハロ-(C1~C6)-アルキル、(C3~C6)-シクロアルキル、R1O、R2(O)nSまたはR1O-(C1~C6)-アルキルであり、
Yは、ハロゲン、(C1~C6)-アルキル、ハロ-(C1~C6)-アルキル、R1OまたはR2(O)nSであり、
Zは、(C1~C6)-アルキル、(C3~C6)-シクロアルキル、(C3~C6)-シクロアルキル-(C1~C6)-アルキル、(C1~C6)-アルキル-O-(C1~C6)-アルキル、(C1~C6)-ハロアルキル、(C2~C6)-アルケニルまたは(C2~C6)-アルキニルであり、
R1は、(C1~C6)-アルキルまたはハロ-(C1~C6)-アルキルであり、
R2は、(C1~C6)-アルキルであり、
nは、0、1または2である)
を提供する。
式(I)の化合物は塩を形成することができる。適切な塩基は、例えば、有機アミン(トリアルキルアミン、モルホリン、ピペリジンまたはピリジンなど)、およびアンモニウム、アルカリ金属またはアルカリ土類金属の水酸化物、炭酸塩および重炭酸塩、特に水酸化ナトリウム、水酸化カリウム、炭酸ナトリウム、炭酸カリウム、重炭酸ナトリウムおよび重炭酸カリウムである。これらの塩は、酸性水素が農業的に適したカチオン、例えば金属塩、特にアルカリ金属塩またはアルカリ土類金属塩、特にナトリウム塩およびカリウム塩、またはアンモニウム塩、有機アミンによる塩または第四級アンモニウム塩、例えば式[NRR’R’’R’’’]+(式中、R~R’’’はそれぞれ互いに独立に、有機基、特にアルキル、アリール、アラルキルまたはアルキルアリールを表す)のカチオンによって置き換えられた化合物である。(C1~C4)-トリアルキルスルホニウムおよび(C1~C4)-トリアルキルスルホキソニウム塩などのアルキルスルホニウムおよびアルキルスルホキソニウム塩も適している。
RXが、(C1~C3)-アルキルまたは(C1~C3)-アルキル-O-(C1~C3)-アルキルであり、
Xが、ハロゲン、(C1~C3)-アルキル、ハロ-(C1~C3)-アルキル、(C3~C6)-シクロアルキル、R1O、R2(O)nSまたはR1O-(C1~C3)-アルキルであり、
Yが、ハロゲン、(C1~C4)-アルキル、ハロ-(C1~C4)-アルキル、R1OまたはR2(O)nSであり、
Zが、(C1~C4)-アルキル、(C3~C6)-シクロアルキル、(C3~C6)-シクロアルキル-(C1~C3)-アルキル、(C1~C3)-アルキル-O-(C1~C3)-アルキル、(C1~C3)-ハロアルキル、(C2~C6)-アルケニルまたは(C2~C6)-アルキニルであり、
R1が、(C1~C3)-アルキルまたはハロ-(C1~C3)-アルキルであり、
R2が、(C1~C3)-アルキルであり、
nが、0、1または2である、
一般式(I)の化合物が好ましい。
RXが、Me、EtまたはPrであり、
Xが、F、Cl、Br、I、Me、Et、c-Pr、CF3、C2F5、CH2OMe、OMe、SMe、SO2Me、SEtまたはSO2Etであり、
Yが、Cl、Br、I、Me、CF3、CHF2、C2F5、SMeまたはSO2Meであり、
Zが、Me、Et、i-Pr、c-Pr、CH2-c-Pr、(CH2)2OMe、アリルまたはCH2CF3であり、
nが、0、1または2である、
一般式(I)の化合物が特に好ましい。
Me:メチル Et:エチル Ph:フェニル
Pr:プロピル c-Pr:シクロプロピル i-Pr:イソプロピル
-植物を特定の有害生物に対して耐性にするバチルス・チューリンゲンシス(Bacillus thuringiensis)毒素(Bt毒素)を産生することができるトランスジェニック作物植物、例えばワタ(欧州特許出願公開第0142924号明細書、欧州特許出願公開第0193259号明細書)、
-修正された脂肪酸組成を有するトランスジェニック作物植物(国際公開第91/013972号パンフレット)、
-耐病性の増加をもたらす新規な成分または二次代謝物、例えば新規なファイトアレキシンを有する遺伝子改変作物植物(欧州特許出願公開第0309862号明細書、欧州特許出願公開第0464461号明細書)、
-より高い収量およびより高いストレス耐性を有する、光呼吸が減少した遺伝子改変植物(欧州特許出願公開第0305398号明細書)、
-薬学的にまたは診断上重要なタンパク質を産生するトランスジェニック作物植物(「分子ファーミング」)、
-より高い収量またはより良い品質を特徴とするトランスジェニック作物植物、
-例えば、上記の新規な特性の組み合わせによって識別されるトランスジェニック作物植物(「遺伝子スタッキング」)
のいくつかの場合である。
アセトクロール、アシフルオルフェン、アシフルオルフェン-ナトリウム、アクロニフェン、アラクロール、アリドクロール、アロキシジム、アロキシジム-ナトリウム、アメトリン、アミカルバゾン、アミドクロル、アミドスルフロン、アミノシクロピラクロル、アミノシクロピラクロル-カリウム、アミノシクロピラクロル-メチル、アミノピラリド、アミトロール、アンモニウムスルファマート、アニロホス、アシュラム、アトラジン、アザフェニジン、アジムスルフロン、ベフルブタミド、ベナゾリン、ベナゾリン-エチル、ベンフルラリン、ベンフレセート、ベンスルフロン、ベンスルフロン-メチル、ベンスリド、ベンタゾン、ベンゾビシクロン、ベンゾフェナップ、ビシクロピロン(bicyclopyron)、ビフェノックス、ビアラホス、ビアラホス-ナトリウム、ビスピリバック、ビスピリバック-ナトリウム、ブロマシル、ブロモブチド、ブロモフェノキシム、ブロモキシニル、酪酸ブロモキシニル、ブロモキシニルカリウム塩、ヘプタン酸ブロモキシニルおよびオクタン酸ブロモキシニル、ブソキシノン(busoxinone)、ブタクロール、ブタフェナシル、ブタミホス、ブテナクロール、ブトラリン、ブトロキシジム、ブチレート、カフェンストロール、カルベタミド、カルフェントラゾン、カルフェントラゾン-エチル、クロラムベン、クロルブロムロン、クロルフェナック、クロルフェナック-ナトリウム、クロルフェンプロップ、クロルフルレノール、クロルフルレノール-メチル、クロリダゾン、クロリムロン、クロリムロン-エチル、クロルフタリム(chlorophthalim)、クロロトルロン、クロルタール-ジメチル、クロルスルフロン、3-[5-クロロ-4-(トリフルオロメチル)ピリジン-2-イル]-4-ヒドロキシ-1-メチルイミダゾリジン-2-オン、シニドン、シニドンエチル、シンメチリン、シノスルフロン、クラシフォス(clacyfos)、クレトジム、クロジナホップ、クロジナホップ-プロパルギル、クロマゾン、クロメプロップ、クロピラリド、クロランスラム、クロランスラム-メチル、クミルロン、シアナミド、シアナジン、シクロエート、シクロピラニル、シクロピリモレート、シクロスルファムロン、シクロキシジム、シハロホップ、シハロホップ-ブチル、シプラジン、2,4-D、2,4-D-ブトチル、2,
4-D-ブチル、2,4-D-ジメチルアンモニウム、2,4-D-ジオールアミン(diolamin)、2,4-D-エチル、2,4-D2-エチルヘキシル、2,4-D-イソブチル、2,4-D-イソオクチル、2,4-D-イソプロピルアンモニウム、2,4-D-カリウム、2,4-D-トリイソプロパノールアンモニウムおよび2,4-D-トロールアミン、2,4-DB、2,4-DB-ブチル、2,4-DB-ジメチルアンモニウム、2,4-DBイソオクチル、2,4-DB-カリウムおよび2,4-DB-ナトリウム、ダイムロン(ダイムロン)、ダラポン、ダゾメット、n-デカノール、デスメディファム、デトシル-ピラゾレート(detosyl-pyrazolate)(DTP)、ジカンバ、ジクロベニル、2-(2,4-ジクロロベンジル)-4,4-ジメチル-1,2-オキサゾリジン-3-オン、2-(2,5-ジクロロベンジル)-4,4-ジメチル-1,2-オキサゾリジン-3-オン、ジクロルプロップ、ジクロルプロップ-P、ジクロホップ、ジクロホップ-メチル、ジクロホップ-P-メチル、ジクロスラム、ジフェンゾコート、ジフルフェニカン、ジフルフェンゾピル、ジフルフェンゾピル-ナトリウム、ジメフロン、ジメピペレート、ジメタクロール、ジメタメトリン、ジメテナミド、ジメテナミド-P、ジメトラスルフロン、ジニトラミン、ジノテルブ、ジフェナミド、ジクワット、ジクワットジブロミド、ジチオピル、ジウロン、DNOC、エンドタール、EPTC、エスプロカルブ、エタルフルラリン、エタメツルフロン、エタメツルフロン-メチル、エチオジン、エトフメセート、エトキシフェン、エトキシフェン-エチル、エトキシスルフロン、エトベンザニド、F-9600、F-5231、すなわち、N-[2-クロロ-4-フルオロ-5-[4-(3-フルオロプロピル)-4,5-ジヒドロ-5-オキソ-1H-テトラゾール-1-イル]フェニル]エタンスルホンアミド、F-7967、すなわち、3-[7-クロロ-5-フルオロ-2-(トリフルオロメチル)-1H-ベンズイミダゾール-4-イル]-1-メチル-6-(トリフルオロメチル)ピリミジン-2,4(1H,3H)-ジオン、フェノキサプロップ、フェノキサプロップ-P、フェノキサプロップエチル、フェノキサプロップ-P-エチル、フェノキサスルホン、フェンキノトリオン、フェントラザミド、フラムプロップ、フラムプロップ-M-イソプロピル、フラムプロップ-M-メチル、フラザスルフロン、フロラスラム、フロルピラウキシフェン、フロルピラウキシフェン-ベンジル、フルアジホップ、フルアジホップ-P、フルアジホップ-ブチル、フルアジホップ-P-ブチル、フルカルバゾン、フルカルバゾンナトリウム、フルセトスルフロン、フルクロラリン、フルフェナセット、フルフェンピル、フルフェンピルエチル、フルメツラム、フルミクロラック、フルミクロラックペンチル、フルミオキサジン、フルオメツロン、フルレノール、フルレノールブチル、フルレノールジメチルアンモニウムおよびフルレノールメチル、フルオログリコフェン、フルオログリコフェンエチル、フルプロパネート、フルピルスルフロン、フルピルスルフロンメチルナトリウム、フルリドン、フルオロクロリドン、フルロキシピル、フルロキシピルメプチル、フルルタモン、フルチアセット、フルチアセットメチル、フォメサフェン、フォメサフェン-ナトリウム、ホラムスルフロン、ホサミン、グルホシネート、グルホシネートアンモニウム、グルホシネート-P-ナトリウム、グルホシネート-P-アンモニウム、グルホシネート-P-ナトリウム、グリホサート、グリホサートアンモニウム、グリホサートイソプロピルアンモニウム、グリホサートジアンモニウム、グリホサートジメチルアンモニウム、グリホサートカリウム、グリホサートナトリウムおよびグリホサートトリメシウム、H-9201、すなわち、O-(2,4-ジメチル-6-ニトロフェニル)O-エチルイソプロピルホスホルアミドチオエート、ハラウキシフェン、ハラウキシフェン-メチル、ハロサフェン、ハロスルフロン、ハロスルフロンメチル、ハロキシホップ、ハロキシホップ-P、ハロキシホップエトキシエチル、ハロキシホップ-P-エトキシエチル、ハロキシホップメチル、ハロキシホップ-P-メチル、ヘキサジノン、HW-02、すなわち、1-(ジメトキシホスホリル)エチル(2,4-ジクロロフェノキシ)アセテート、4-ヒドロキシ-1-メトキシ-5-メチル-3-[4-(トリフルオロメチル)ピリジン-2-イル]イミダゾリジン-2-オン、4-ヒドロキシ-1-メチル-3-[4-(トリフルオロメチル)ピリジン-2-イル]イミダゾリジン-2-オン、イマザメタベンズ、イマザメタベンズメチル、イマザモックス、イマザモックスアンモニウム、イマザピック、イマザピックアンモニウム、イマザピル、イマザピルイソプロピルアンモニウム、イマザキン、イマザキンアンモニウム、イマゼタピル、イマゼタピルイモニウム、イマゾスルフロン、インダノファン、インダジフラム、ヨードスルフロン、ヨードスルフロンメチルナトリウム、イオキシニル、イオキシニルオクタノエート、イオキシニルカリウムおよびイオキシニルナトリウム、イプフェンカルバゾン、イソプロツロン、イソウロン、イソキサベン、イソキサフルトール、カルブチレート、KUH-043、すなわち、3-({[5-(ジフルオロメチル)-1-メチル-3-(トリフルオロメチル)-1H-ピラゾール-4-イル]メチル}スルホニル)-5,5-ジメチル-4,5-ジヒドロ-1,2-オキサゾール、ケトスピラドックス、ラクトフェン、レナシル、リニュロン、MCPA、MCPA-ブトチル、MCPA-ジメチルアンモニウム、MCPA-2-エチルヘキシル、MCPA-イソプロピルアンモニウム、MCPA-カリウムおよびMCPA-ナトリウム、MCPB、MCPB-メチル、MCPB-エチルおよびMCPB-ナトリウム、メコプロップ、メコプロップナトリウム、およびメコプロップブトチル、メコプロップ-P、メコプロップ-P-ブトチル、メコプロップ-P-ジメチルアンモニウム、メコプロップ-P-2-エチルヘキシルおよびメコプロップ-P-カリウム、メフェナセット、メフルイジド、メソスルフロン、メソスルフロン-メチル、メソトリオン、メタベンズチアズロン、メタム、メタミホップ、メタミトロン、メタザクロール、メタゾスルフロン、メタベンズチアズロン、メチオピルスルフロン、メチオゾリン、メチルイソチオシアネート、メトブロムロン、メトラクロール、S-メトラクロール、メトスラム、メトクスロン、メトリブジン、メトスルフロン、メトスルフロン-メチル、モリネート、モノリニュロン、モノスルフロン、モノスルフロンエステル、MT-5950、すなわち、N-[3-クロロ-4-(1-メチルエチル)-フェニル]-2-メチルペンタンアミド、NGGC-011、ナプロパミド、NC-310、すなわち、4-(2,4-ジクロロベンゾイル)-1-メチル-5-ベンジルオキシピラゾール、ネブロン、ニコスルフロン、ノナン酸(ペラ
ルゴン酸)、ノルフルラゾン、オレイン酸(脂肪酸)、オルベンカルブ、オルソスルファムロン、オリザリン、オキサジアルギル、オキサジアゾン、オキサスルフロン、オキサジクロメホン、オキソトリオン(ランコトリオン)、オキシフルオロフェン、パラコート、パラコートジクロライド、ペブレート、ペンディメタリン、ペノキススラム、ペンタクロロフェノール、ペントキサゾン、ペトキサミド、石油、フェンメディファム、ピクロラム、ピコリナフェン、ピノキサデン、ピペロホス、プレチラクロール、プリミスルフロン、プリミスルフロン-メチル、プロジアミン、プロホキシジム、プロメトン、プロメトリン、プロパクロール、プロパニル、プロパキザホップ、プロパジン、プロファム、プロピソクロール、プロポキシカルバゾン、プロポキシカルバゾンナトリウム、プロピリスルフロン、プロピザミド、プロスルホカルブ、プロスルフロン、ピラクロニル、ピラフルフェン、ピラフルフェンエチル、ピラスルホトール、ピラゾリネート(ピラゾレート)、ピラゾスルフロン、ピラゾスルフロンエチル、ピラゾキシフェン、ピリバムベンズ、ピリバムベンズイソプロピル、ピリバムベンズプロピル、ピリベンゾキシム、ピリブチカルブ、ピリダフォル、ピリデート、ピリフタリド、ピリミノバック、ピリミノバックメチル、ピリミスルファン、ピリチオバック、ピリチオバックナトリウム、ピロキサスルホン、ピロキシスラム、キンクロラック、キンメラック、キノクラミン、キザロホップ、キザロホップ-エチル、キザロホップ-P、キザロホップ-P-エチル、キザロホップ-P-テフリル、リムスルフロン、サフルフェナシル、セトキシジム、シデュロン、シマジン、シメトリン、スルコトリオン、スルフェントラゾン、スルホメツロン、スルホメツロンメチル、スルホスルフロン、SYN-523、SYP-249、すなわち、1-エトキシ-3-メチル-1-オキソブタ-3-エン-2-イル5-[2-クロロ-4-(トリフルオロメチル)フェノキシ]-2-ニトロベンゾエート、SYP-300、すなわち、1-[7-フルオロ-3-オキソ-4-(プロパ-2-イン-1-イル)-3,4-ジヒドロ-2H-1,4-ベンゾキサジン-6-イル]-3-プロピル-2-チオキソイミダゾリジン-4,5-ジオン、2,3,6-TBA、TCA(トリフルオロ酢酸)、TCA-ナトリウム、テ
ブチウロン、テフリルトリオン、テンボトリオン、テプラロキシジム、ターバシル、テルブカルブ、テルブメトン、テルブチラジン、テルブトリン、テニルクロール、チアゾピル、チエンカルバゾン、チエンカルバゾンメチル、チフェンスルフロン、チフェンスルフロンメチル、チオベンカルブ、チアフェナシル、トルピラレート、トプラメゾン、トラルコキシジム、トリアファモン、トリアレート、トリアスルフロン、トリアジフラム、トリベヌロン、トリベヌロンメチル、トリクロピル、トリエタジン、トリフロキシスルフロン、トリフロキシスルフロンナトリウム、トリフルジモキサジン、トリフルラリン、トリフルスルフロン、トリフルスルフロンメチル、トリトスルフロン、尿素硫酸塩、バーノレート、ZJ-0862、すなわち、3,4-ジクロロ-N-{2-[(4,6-ジメトキシピリミジン-2-イル)オキシ]ベンジル}アニリン、および以下の化合物:
アシベンゾラル、アシベンゾラル-S-メチル、5-アミノレブリン酸、アンシミドール、6-ベンジルアミノプリン、ブラシノライド、カテコール、クロルメコートクロリド、クロプロップ、シクラニリド、3-(シクロプロパ-1-エニル)プロピオン酸、ダミノジド、ダゾメット、n-デカノール、ジケグラック、ジケグラック-ナトリウム、エンドタール、エンドタール-ジカリウム、-ジナトリウムおよびモノ(N,N-ジメチルアルキルアンモニウム)、エテホン、フルメトラリン、フルレノール、フルレノール-ブチル、フルルプリミドール、ホルクロルフェニュロン、ジベレリン酸、イナベンフィド、インドール-3-酢酸(IAA)、4-インドール-3-イル酪酸、イソプロチオラン、プロベナゾール、ジャスモン酸、ジャスモン酸メチルエステル、マレイン酸ヒドラジド、メピコートクロリド、1-メチルシクロプロペン、2-(1-ナフチル)アセトアミド、1-ナフチル酢酸、2-ナフチルオキシ酢酸、ニトロフェノレート混合物、4-オキソ-4[(2-フェニルエチル)アミノ]酪酸、パクロブトラゾール、N-フェニルフタルアミド酸、プロヘキサジオン、プロヘキサジオン-カルシウム、プロヒドロジャスモン、サリチル酸、ストリゴラクトン、テクナゼン、チジアズロン、トリアコンタノール、トリネキサパック、トリネキサパック-エチル、チトデフ、ウニコナゾール、ウニコナゾール-P。
(式中、記号および指数は以下の通りに定義される:
nAは0~5、好ましくは0~3の自然数であり;
RA 1はハロゲン、(C1~C4)-アルキル、(C1~C4)-アルコキシ、ニトロまたは(C1~C4)-ハロアルキルであり;
WAはNおよびOからなる群の1~3個の環ヘテロ原子を有する部分不飽和または芳香族5員複素環からなる群の非置換または置換二価複素環式基であり、少なくとも1個の窒素原子および最大1個の酸素原子が環中に存在し、
mAは0または1であり;
RA 2はORA 3、SRA 3またはNRA 3RA 4、または少なくとも1個の窒素原子と最大3個の好ましくはOおよびSからなる群のヘテロ原子とを有する飽和もしくは不飽和の3~7員複素環であり、窒素原子を介して(S1)中のカルボニル基に結合しており、非置換である、または(C1~C4)-アルキル、(C1~C4)-アルコキシもしくは場合により置換されたフェニルからなる群の基によって置換されており、好ましくは式ORA 3、NHRA 4またはN(CH3)2、特に式ORA 3の基であり;
RA 3は水素、または好ましくは合計1~18個の炭素原子を有する非置換もしくは置換脂肪族炭化水素基であり;
RA 4は水素、(C1~C6)-アルキル、(C1~C6)-アルコキシまたは置換もしくは非置換フェニルであり;
RA 5はH、(C1~C8)-アルキル、(C1~C8)-ハロアルキル、(C1~C4)-アルコキシ-(C1~C8)-アルキル、シアノまたはCOORA 9であり、RA 9は水素、(C1~C8)-アルキル、(C1~C8)-ハロアルキル、(C1~C4)-アルコキシ-(C1~C4)-アルキル、(C1~C6)-ヒドロキシアルキル、(C3~C12)-シクロアルキルまたはトリ-(C1~C4)-アルキルシリルであり;
RA 6、RA 7、RA 8は同一であるまたは異なり、水素、(C1~C8)-アルキル、(C1~C8)-ハロアルキル、(C3~C12)-シクロアルキルまたは置換もしくは非置換フェニルである)
好ましくは:
a)ジクロロフェニルピラゾリン-3-カルボン酸型の化合物(S1a)、好ましくは1-(2,4-ジクロロフェニル)-5-(エトキシカルボニル)-5-メチル-2-ピラゾリン-3-カルボン酸、エチル1-(2,4-ジクロロフェニル)-5-(エトキシカルボニル)-5-メチル-2-ピラゾリン-3-カルボキシレート(S1-1)(「メフェンピル-ジエチル」)、および国際公開第91/07874号パンフレットに記載される関連化合物などの化合物;
b)ジクロロフェニルピラゾールカルボン酸の誘導体(S1b)、好ましくはエチル1-(2,4-ジクロロフェニル)-5-メチルピラゾール-3-カルボキシレート(S1-2)、エチル1-(2,4-ジクロロフェニル)-5-イソプロピルピラゾール-3-カルボキシレート(S1-3)、エチル1-(2,4-ジクロロフェニル)-5-(1,1-ジメチルエチル)ピラゾール-3-カルボキシレート(S1-4)ならびに欧州特許第333131号明細書および欧州特許第269806号明細書に記載される関連化合物などの化合物;
c)1,5-ジフェニルピラゾール-3-カルボン酸の誘導体(S1c)、好ましくはエチル1-(2,4-ジクロロフェニル)-5-フェニルピラゾール-3-カルボキシレート(S1-5)、メチル1-(2-クロロフェニル)-5-フェニルピラゾール-3-カルボキシレート(S1-6)および欧州特許第268554号明細書に記載される関連化合物などの化合物、例えば;
d)トリアゾールカルボン酸型の化合物(S1d)、好ましくはフェンクロラゾール(-エチルエステル)、すなわちエチル1-(2,4-ジクロロフェニル)-5-トリクロロメチル-(1H)-1,2,4-トリアゾール-3-カルボキシレート(S1-7)、ならびに欧州特許第174562号明細書および欧州特許第346620号明細書に記載される関連化合物などの化合物;
e)5-ベンジル-もしくは5-フェニル-2-イソオキサゾリン-3-カルボン酸または5,5-ジフェニル-2-イソオキサゾリン-3-カルボン酸型の化合物(S1e)、好ましくはエチル5-(2,4-ジクロロベンジル)-2-イソオキサゾリン-3-カルボキシレート(S1-8)または5-フェニル-2-イソオキサゾリン-3-カルボキシレート(S1-9)および国際公開第91/08202号パンフレットに記載される関連化合物、または特許出願、国際公開第95/07897号パンフレットに記載される5,5-ジフェニル-2-イソオキサゾリン-3-カルボン酸(S1-10)またはエチル5,5-ジフェニル-2-イソオキサゾリン-3-カルボキシレート(S1-11)(「イソキサジフェン-エチル」)または、n-プロピル5,5-ジフェニル-2-イソオキサゾリン-3-カルボキシレート(S1-12)またはエチル5-(4-フルオロフェニル)-5-フェニル-2-イソオキサゾリン-3-カルボキシレート(S1-13)などの化合物。
RB 1はハロゲン、(C1~C4)-アルキル、(C1~C4)-アルコキシ、ニトロまたは(C1~C4)-ハロアルキルであり;
nBは0~5、好ましくは0~3の自然数であり;
RB 2はORB 3、SRB 3、NRB 3RB 4、または少なくとも1個の窒素原子と最大3個の好ましくはOおよびSの群のヘテロ原子とを有する飽和もしくは不飽和の3~7員複素環であり、窒素原子を介して(S2)中のカルボニル基に結合しており、非置換である、または(C1~C4)-アルキル、(C1~C4)-アルコキシもしくは場合により置換されたフェニルの群の基によって置換されており、好ましくは式ORB 3、NHRB 4またはN(CH3)2、特に式ORB 3の基であり;
RB 3は水素または好ましくは合計1~18個の炭素原子を有する非置換もしくは置換脂肪族炭化水素基であり;
RB 4は水素、(C1~C6)-アルキル、(C1~C6)-アルコキシまたは置換もしくは非置換フェニルであり;
TBは非置換である、または1個もしくは2個の(C1~C4)-アルキル基によって、または[(C1~C3)-アルコキシ]カルボニルによって置換された(C1またはC2)-アルカンジイル鎖である);
好ましくは:
a)8-キノリンオキシ酢酸型の化合物(S2a)、好ましくは
1-メチルヘキシル(5-クロロ-8-キノリンオキシ)アセテート(「クロキントセット-メキシル」)(S2-1)、
(1,3-ジメチルブタ-1-イル)(5-クロロ-8-キノリンオキシ)アセテート(S2-2)、
4-アリルオキシブチル(5-クロロ-8-キノリンオキシ)アセテート(S2-3)、
1-アリルオキシプロパ-2-イル(5-クロロ-8-キノリンオキシ)アセテート(S2-4)、
エチル(5-クロロ-8-キノリンオキシ)アセテート(S2-5)、
メチル(5-クロロ-8-キノリンオキシ)アセテート(S2-6)、
アリル(5-クロロ-8-キノリンオキシ)アセテート(S2-7)、
2-(2-プロピリデンイミノキシ)-1-エチル(5-クロロ-8-キノリンオキシ)アセテート(S2-8)、2-オキソプロパ-1-イル(5-クロロ-8-キノリンオキシ)アセテート(S2-9)ならびに欧州特許第86750号明細書、欧州特許第94349号明細書および欧州特許第191736号明細書または欧州特許第0492366号明細書に記載される関連化合物、ならびに(5-クロロ-8-キノリンオキシ)酢酸(S2-10)、その水和物および塩、例えば国際公開第2002/34048号パンフレットに記載されるそのリチウム、ナトリウム、カリウム、カルシウム、マグネシウム、アルミニウム、鉄、アンモニウム、四級アンモニウム、スルホニウムまたはホスホニウム塩;
b)(5-クロロ-8-キノリンオキシ)マロン酸型の化合物(S2b)、好ましくはジエチル(5-クロロ-8-キノリンオキシ)マロネート、ジアリル(5-クロロ-8-キノリンオキシ)マロネート、メチルエチル(5-クロロ-8-キノリンオキシ)マロネートおよび欧州特許第0 582 198号明細書に記載される関連化合物などの化合物。
RC 1は(C1~C4)-アルキル、(C1~C4)-ハロアルキル、(C2~C4)-アルケニル、(C2~C4)-ハロアルケニル、(C3~C7)-シクロアルキル、好ましくはジクロロメチルであり;
RC 2、RC 3は同一であるまたは異なり、水素、(C1~C4)アルキル、(C2~C4)アルケニル、(C2~C4)アルキニル、(C1~C4)ハロアルキル、(C2~C4)ハロアルケニル、(C1~C4)アルキルカルバモイル-(C1~C4)アルキル、(C2~C4)アルケニルカルバモイル-(C1~C4)アルキル、(C1~C4)アルコキシ-(C1~C4)アルキル、ジオキソラニル-(C1~C4)アルキル、チアゾリル、フリル、フリルアルキル、チエニル、ピペリジル、置換もしくは非置換フェニルである、あるいはRC 2とRC 3が一緒になって、置換または非置換複素環、好ましくはオキサゾリジン、チアゾリジン、ピペリジン、モルホリン、ヘキサヒドロピリミジンまたはベンゾオキサジン環を形成する)
好ましくは:
出芽前薬害軽減剤(土壌作用薬害軽減剤)として頻繁に使用されるジクロロアセトアミド型の有効成分、例えば
「ジクロルミド」(N,N-ジアリル-2,2-ジクロロアセトアミド)(S3-1)、
Stauffer製の「R-29148」(3-ジクロロアセチル-2,2,5-トリメチル-1,3-オキサゾリジン)(S3-2)、
Stauffer製の「R-28725」(3-ジクロロアセチル-2,2-ジメチル-1,3-オキサゾリジン)(S3-3)、
「ベノキサコール」(4-ジクロロアセチル-3,4-ジヒドロ-3-メチル-2H-1,4-ベンゾオキサジン)(S3-4)、
PPG Industries製の「PPG-1292」(N-アリル-N-[(1,3-ジオキソラン-2-イル)メチル]ジクロロアセトアミド)(S3-5)、
Sagro-Chem製の「DKA-24」(N-アリル-N-[(アリルアミノカルボニル)メチル]ジクロロアセトアミド)(S3-6)、
NitrokemiaまたはMonsanto製の「AD-67」または「MON 4660」(3-ジクロロアセチル-1-オキサ-3-アザスピロ[4.5]デカン)(S3-7)、
TRI-Chemical RT製の「TI-35」(1-ジクロロアセチルアゼパン)(S3-8)、
「ジクロノン(diclonon)」(ジシクロノン(dicyclonon))または「BAS145138」または「LAB145138」(S3-9)
BASF製の((RS)-1-ジクロロアセチル-3,3,8a-トリメチルペルヒドロピロロ[1,2-a]ピリミジン-6-オン)、
「フリラゾール」または「MON 13900」((RS)-3-ジクロロアセチル-5-(2-フリル)-2,2-ジメチルオキサゾリジン)(S3-10);およびその(R)異性体(S3-11)。
ADはSO2-NRD 3-COまたはCO-NRD 3-SO2であり、
XDはCHまたはNであり;
RD 1はCO-NRD 5RD 6またはNHCO-RD 7であり;
RD 2はハロゲン、(C1~C4)-ハロアルキル、(C1~C4)-ハロアルコキシ、ニトロ、(C1~C4)-アルキル、(C1~C4)-アルコキシ、(C1~C4)-アルキルスルホニル、(C1~C4)-アルコキシカルボニルまたは(C1~C4)-アルキルカルボニルであり;
RD 3は水素、(C1~C4)-アルキル、(C2~C4)-アルケニルまたは(C2~C4)-アルキニルであり;
RD 4はハロゲン、ニトロ、(C1~C4)-アルキル、(C1~C4)-ハロアルキル、(C1~C4)-ハロアルコキシ、(C3~C6)-シクロアルキル、フェニル、(C1~C4)-アルコキシ、シアノ、(C1~C4)-アルキルチオ、(C1~C4)-アルキルスルフィニル、(C1~C4)-アルキルスルホニル、(C1~C4)-アルコキシカルボニルまたは(C1~C4)-アルキルカルボニルであり;
RD 5は水素、(C1~C6)-アルキル、(C3~C6)-シクロアルキル、(C2~C6)-アルケニル、(C2~C6)-アルキニル、(C5~C6)-シクロアルケニル、フェニルまたは窒素、酸素および硫黄からなる群のvDヘテロ原子を含有する3~6員ヘテロシクリルであり、後の7つの基は、ハロゲン、(C1~C6)-アルコキシ、(C1~C6)-ハロアルコキシ、(C1~C2)-アルキルスルフィニル、(C1~C2)-アルキルスルホニル、(C3~C6)-シクロアルキル、(C1~C4)-アルコキシカルボニル、(C1~C4)-アルキルカルボニルおよびフェニル、ならびに環状基の場合、また(C1~C4)-アルキルおよび(C1~C4)-ハロアルキルからなる群のvD置換基によって置換されており;
RD 6は水素、(C1~C6)-アルキル、(C2~C6)-アルケニルまたは(C2~C6)-アルキニルであり、後の3つの基は、ハロゲン、ヒドロキシ、(C1~C4)-アルキル、(C1~C4)-アルコキシおよび(C1~C4)-アルキルチオからなる群のvD基によって置換されている、あるいは
RD 5とRD 6がこれらを有する窒素原子と一緒になって、ピロリジニルまたはピペリジニル基を形成し;
RD 7は水素、(C1~C4)-アルキルアミノ、ジ-(C1~C4)-アルキルアミノ、(C1~C6)-アルキル、(C3~C6)-シクロアルキルであり、後の2つの基は、ハロゲン、(C1~C4)-アルコキシ、(C1~C6)-ハロアルコキシおよび(C1~C4)-アルキルチオ、ならびに環状基の場合、また(C1~C4)-アルキルおよび(C1~C4)-ハロアルキルからなる群のvD置換基によって置換されており;
nDは0、1または2であり;
mDは1または2であり;
vDは0、1、2または3である);
これらのうち、例えば、国際公開第97/45016号パンフレットから知られている、例えば以下の式(S4a)のN-アシルスルホンアミド型の化合物
RD 7は(C1~C6)-アルキル、(C3~C6)-シクロアルキルであり、後の2つの基は、ハロゲン、(C1~C4)-アルコキシ、(C1~C6)-ハロアルコキシおよび(C1~C4)-アルキルチオ、ならびに環式基の場合、また(C1~C4)-アルキルおよび(C1~C4)-ハロアルキルからなる群のvD置換基によって置換されており;
RD 4はハロゲン、(C1~C4)-アルキル、(C1~C4)-アルコキシ、CF3であり;
mDは1または2であり;
vDは0、1、2、または3である)
およびまた
例えば、国際公開第99/16744号パンフレットから知られている、例えば以下の式(S4b)のアシルスルファモイルベンズアミド
RD 5=シクロプロピルおよび(RD 4)=2-OMe(「シプロスルファミド」、S4-1)、
RD 5=シクロプロピルおよび(RD 4)=5-Cl-2-OMe(S4-2)、
RD 5=エチルおよび(RD 4)=2-OMe(S4-3)、
RD 5=イソプロピルおよび(RD 4)=5-Cl-2-OMe(S4-4)および
RD 5=イソプロピルおよび(RD 4)=2-OMe(S4-5)
であるもの、およびまた
例えば、欧州特許第365484号明細書から知られている、式(S4c)のN-アシルスルファモイルフェニル尿素型の化合物
RD 8およびRD 9は独立に、水素、(C1~C8)-アルキル、(C3~C8)-シクロアルキル、(C3~C6)-アルケニル、(C3~C6)-アルキニルを表し、
RD 4はハロゲン、(C1~C4)-アルキル、(C1~C4)-アルコキシ、CF3であり、
mDは1または2である);
例えば
1-[4-(N-2-メトキシベンゾイルスルファモイル)フェニル]-3-メチル尿素(「メトカミフェン(metcamifen)、S4-6)、
1-[4-(N-2-メトキシベンゾイルスルファモイル)フェニル]-3,3-ジメチル尿素、
1-[4-(N-4,5-ジメチルベンゾイルスルファモイル)フェニル]-3-メチル尿素、
およびまた
例えば、中国特許第101838227号明細書から知られている、式(S4d)のN-フェニルスルホニルテレフタルアミド
RD 4がハロゲン、(C1~C4)-アルキル、(C1~C4)-アルコキシ、CF3であり;
mDが1または2であり;
RD 5が水素、(C1~C6)-アルキル、(C3~C6)-シクロアルキル、(C2~C6)-アルケニル、(C2~C6)-アルキニル、(C5~C6)-シクロアルケニルである
もの。
国際公開第2004/084631号パンフレット、国際公開第2005/015994号パンフレット、国際公開第2005/016001号パンフレットに記載される、エチル3,4,5-トリアセトキシベンゾエート、3,5-ジメトキシ-4-ヒドロキシ安息香酸、3,5-ジヒドロキシ安息香酸、4-ヒドロキシサリチル酸、4-フルオロサリチル酸、2-ヒドロキシケイ皮酸、2,4-ジクロロケイ皮酸。
国際公開第2005/112630号パンフレットに記載される、1-メチル-3-(2-チエニル)-1,2-ジヒドロキノキサリン-2-オン、1-メチル-3-(2-チエニル)-1,2-ジヒドロキノキサリン-2-チオン、1-(2-アミノエチル)-3-(2-チエニル)-1,2-ジヒドロキノキサリン-2-オン塩酸塩、1-(2-メチルスルホニルアミノエチル)-3-(2-チエニル)-1,2-ジヒドロキノキサリン-2-オン。
RE 1、RE 2は独立に、ハロゲン、(C1~C4)-アルキル、(C1~C4)-アルコキシ、(C1~C4)-ハロアルキル、(C1~C4)-アルキルアミノ、ジ-(C1~C4)-アルキルアミノ、ニトロであり;
AEはCOORE 3またはCOSRE 4であり、
RE 3、RE 4は独立に、水素、(C1~C4)-アルキル、(C2~C6)-アルケニル、(C2~C4)-アルキニル、シアノアルキル、(C1~C4)-ハロアルキル、フェニル、ニトロフェニル、ベンジル、ハロベンジル、ピリジニルアルキルおよびアルキルアンモニウムであり、
nE 1は0または1であり、
nE 2、nE 3は独立に、0、1または2である)
好ましくは:
ジフェニルメトキシ酢酸、
エチルジフェニルメトキシアセテート、
メチルジフェニルメトキシアセテート(CAS登録番号41858-19-9)(S7-1)。
XFはCHまたはNであり、
nFは、XF=Nの場合、0~4の整数であり、
XF=CHの場合、0~5の整数であり、
RF 1はハロゲン、(C1~C4)-アルキル、(C1~C4)-ハロアルキル、(C1~C4)-アルコキシ、(C1~C4)-ハロアルコキシ、ニトロ、(C1~C4)-アルキルチオ、(C1~C4)-アルキルスルホニル、(C1~C4)-アルコキシカルボニル、場合により置換されたフェニル、場合により置換されたフェノキシであり、
RF 2は水素または(C1~C4)-アルキルであり、
RF 3は水素、(C1~C8)-アルキル、(C2~C4)-アルケニル、(C2~C4)-アルキニルまたはアリールであり、上記の各炭素含有基の各々は非置換である、または1つもしくは複数の、好ましくは最大3つの、ハロゲンおよびアルコキシからなる群から選択される同一のもしくは異なる基によって置換されている)
またはその塩、
好ましくは、
XFがCHであり、
nFが0~2の整数であり、
RF 1がハロゲン、(C1~C4)-アルキル、(C1~C4)-ハロアルキル、(C1~C4)-アルコキシ、(C1~C4)-ハロアルコキシであり、
RF 2が水素または(C1~C4)-アルキルであり、
RF 3が水素、(C1~C8)-アルキル、(C2~C4)-アルケニル、(C2~C4)-アルキニルまたはアリールであり、上記の炭素含有基の各々が非置換である、または1つもしくは複数の、好ましくは最大3つの、ハロゲンおよびアルコキシからなる群の同一のもしくは異なる基によって置換されている、
化合物またはその塩。
国際公開第1999/000020号パンフレットに記載される、1,2-ジヒドロ-4-ヒドロキシ-1-エチル-3-(5-テトラゾリルカルボニル)-2-キノロン(CAS登録番号219479-18-2)、1,2-ジヒドロ-4-ヒドロキシ-1-メチル-3-(5-テトラゾリルカルボニル)-2-キノロン(CAS登録番号95855-00-8)。
式(S10a)または(S10b)の化合物
RG 1はハロゲン、(C1~C4)-アルキル、メトキシ、ニトロ、シアノ、CF3、OCF3であり、
YG、ZGは互いに独立に、OまたはSを表し、
nGは0~4の整数であり、
RG 2は(C1~C16)-アルキル、(C2~C6)-アルケニル、(C3~C6)-シクロアルキル、アリール;ベンジル、ハロベンジルであり、
RG 3は水素または(C1~C6)-アルキルである)。
メトラクロール損傷に対するキビ/モロコシの種子粉衣薬害軽減剤として知られる、「オキサベトリニル」((Z)-1,3-ジオキソラン-2-イルメトキシイミノ(フェニル)アセトニトリル)(S11-1)、
メトラクロール損傷に対するキビ/モロコシの種子粉衣薬害軽減剤として知られる、「フルキソフェニム」(1-(4-クロロフェニル)-2,2,2-トリフルオロ-1-エタノンO-(1,3-ジオキソラン-2-イルメチル)オキシム)(S11-2)、および
メトラクロール損傷に対するキビ/モロコシの種子粉衣薬害軽減剤として知られる、「シオメトリニル(cyometrinil)」または「CGA-43089」((Z)-シアノメトキシイミノ(フェニル)アセトニトリル)(S11-3)。
チオカルバメート系除草剤損傷に対するトウモロコシの種子粉衣薬害軽減剤として知られる、「ナフタル酸無水物」(1,8-ナフタレンジカルボン酸無水物)(S13-1)、
播種したイネのプレチラクロールの薬害軽減剤として公知の、「フェンクロリム」(4,6-ジクロロ-2-フェニルピリミジン)(S13-2)、
アラクロールおよびメトラクロール損傷に対するキビ/ソルガムの種子粉衣薬害軽減剤として公知の、「フルラゾール」(ベンジル2-クロロ-4-トリフルオロメチル-1,3-チアゾール-5-カルボキシレート)(S13-3)、
「CL 304415」(CAS登録番号31541-57-8)
イミダゾリノンによる損傷に対するトウモロコシの薬害軽減剤として公知の、American Cyanamid製の(4-カルボキシ-3,4-ジヒドロ-2H-1-ベンゾピラン-4-酢酸)(S13-4)、
トウモロコシの薬害軽減剤として公知の、Nitrokemia製の「MG 191」(CAS登録番号96420-72-3)(2-ジクロロメチル-2-メチル-1,3-ジオキソラン)(S13-5)、
「MG 838」(CAS登録番号133993-74-5)
Nitrokemia製(2-プロペニル1-オキサ-4-アザスピロ[4.5]デカン-4-カルボジチオエート)(S13-6)、
「ジスルホトン」(O,O-ジエチルS-2-エチルチオエチルホスホロジチオエート)(S13-7)、
「ジエトレート」(O,O-ジエチルO-フェニルホスホロチオエート)(S13-8)、
「メフェネート」(4-クロロフェニルメチルカルバメート)(S13-9)。
除草剤モリネートによる損傷に対するイネの薬害軽減剤として知られる、「ジメピペレート」または「MY-93」(S-1-メチル-1-フェニルエチルピペリジン-1-カルボチオエート)、
除草剤イマゾスルフロンによる損傷に対するイネの薬害軽減剤として知られる、「ダイムロン」または「SK 23」(1-(1-メチル-1-フェニルエチル)-3-p-トリル尿素)、
ある除草剤による損傷に対するイネの薬害軽減剤として知られる、「クミルロン」=「JC-940」(3-(2-クロロフェニルメチル)-1-(1-メチル-1-フェニルエチル)尿素、特開60087254号明細書参照)、
ある除草剤による損傷に対するイネの薬害軽減剤として知られる、「メトキシフェノン」または「NK 049」(3,3’-ジメチル-4-メトキシベンゾフェノン)、
ある除草剤によるイネの損傷に対する薬害軽減剤として知られる、Kumiai製の「CSB」(1-ブロモ-4-(クロロメチルスルホニル)ベンゼン)(CAS登録番号54091-06-4)。
式(S15)の化合物またはその互変異性体
RH 1は(C1~C6)-ハロアルキル基であり、
RH 2は水素またはハロゲンであり、
RH 3、RH 4は互いに独立に、水素、(C1~C16)-アルキル、(C2~C16)-アルケニルまたは(C2~C16)-アルキニル、
(後者の3つの基の各々は非置換である、またはハロゲン、ヒドロキシル、シアノ、(C1~C4)-アルコキシ、(C1~C4)-ハロアルコキシ、(C1~C4)-アルキルチオ、(C1~C4)-アルキルアミノ、ジ[(C1~C4)-アルキル]アミノ、[(C1~C4)-アルコキシ]カルボニル、[(C1~C4)-ハロアルコキシ]カルボニル、非置換もしくは置換(C3~C6)-シクロアルキル、非置換もしくは置換フェニル、非置換もしくは置換ヘテロシクリルの群の1つもしくは複数の基によって置換されている)、
または(C3~C6)-シクロアルキル、(C4~C6)-シクロアルケニル、環の片側で4~6員飽和もしくは不飽和炭素環式環と融合した(C3~C6)-シクロアルキル、または環の片側で4~6員飽和もしくは不飽和炭素環式環と融合した(C4~C6)-シクロアルケニル
(後の4つの基の各々は、非置換である、またはハロゲン、ヒドロキシル、シアノ、(C1~C4)-アルキル、(C1~C4)-ハロアルキル、(C1~C4)-アルコキシ、(C1~C4)-ハロアルコキシ、(C1~C4)-アルキルチオ、(C1~C4)-アルキルアミノ、ジ[(C1~C4)-アルキル]アミノ、[(C1~C4)-アルコキシ]カルボニル、[(C1~C4)-ハロアルコキシ]カルボニル、非置換もしくは置換(C3~C6)-シクロアルキル、非置換もしくは置換フェニル、および非置換もしくは置換ヘテロシクリルからなる群の1つもしくは複数の基によって置換されている)
を表す、
あるいは
RH 3は(C1~C4)-アルコキシ、(C2~C4)-アルケニルオキシ、(C2~C6)-アルキニルオキシまたは(C2~C4)-ハロアルコキシであり、
RH 4は水素または(C1~C4)-アルキルである、あるいは
RH 3およびRH 4は、直接結合した窒素原子と一緒になって、窒素原子と同様に、さらなる環ヘテロ原子、好ましくは最大2個のN、OおよびSの群のさらなる環ヘテロ原子を含有してもよく、非置換である、またはハロゲン、シアノ、ニトロ、(C1~C4)-アルキル、(C1~C4)-ハロアルキル、(C1~C4)-アルコキシ、(C1~C4)-ハロアルコキシおよび(C1~C4)-アルキルチオの群の1つもしくは複数の基によって置換された4~8員複素環式環を表す)。
(2,4-ジクロロフェノキシ)酢酸(2,4-D)、
(4-クロロフェノキシ)酢酸、
(R,S)-2-(4-クロロ-o-トリルオキシ)プロピオン酸(メコプロップ)、
4-(2,4-ジクロロフェノキシ)酪酸(2,4-DB)、
(4-クロロ-o-トリルオキシ)酢酸(MCPA)、
4-(4-クロロ-o-トリルオキシ)酪酸、
4-(4-クロロフェノキシ)酪酸、
3,6-ジクロロ-2-メトキシ安息香酸(ジカンバ)、
1-(エトキシカルボニル)エチル3,6-ジクロロ-2-メトキシベンゾエート(ラクチジクロル-エチル)。
1)バチルス・チューリンゲンシス(Bacillus thuringiensis)由来の殺虫性結晶タンパク質またはその殺虫性部分、例えばCrickmoreら(Microbiology and Molecular Biology Reviews 1998、62、807~813)によって編集され、http://www.lifesci.sussex.ac.uk/Home/Neil_Crickmore/Bt/)でオンラインでバチルス・チューリンゲンシス(Bacillus thuringiensis)毒素命名法においてCrickmoreら(2005)によって更新された殺虫性結晶タンパク質またはその殺虫性部分、例えばCryタンパク質クラスCry1Ab、Cry1Ac、Cry1B、Cry1C、Cry1D、Cry1F、Cry2Ab、Cry3AaもしくはCry3Bbのタンパク質またはその殺虫性部分(例えば、欧州特許第1999141号明細書および国際公開第2007/107302号パンフレット)、または米国特許出願第12/249016号明細書に記載される合成遺伝子によってコードされるタンパク質;または
2)バチルス・チューリンゲンシス(Bacillus thuringiensis)以外の第2の結晶タンパク質またはその部分の存在下で殺虫性となるバチルス・チューリンゲンシス(Bacillus thuringiensis)由来の結晶タンパク質またはその部分、例えばCy34およびCy35結晶タンパク質で構成された二成分毒素(Nat.Biotechnol.2001、19、668~72;Applied Environm.Microbiol.2006、71、1765~1774)またはCry1AもしくはCry1Fタンパク質およびCry2AaもしくはCry2AbもしくはCry2Aeタンパク質で構成された二成分毒素(米国特許出願第12/214022号明細書および欧州特許第08010791.5号明細書);または
3)バチルス・チューリンゲンシス(Bacillus thuringiensis)由来の2つの異なる殺虫性結晶タンパク質の部分を含むハイブリッド殺虫性タンパク質、例えば上記の1)のタンパク質のハイブリッドまたは上記の2)のタンパク質のハイブリッド、例えばトウモロコシイベントMON98034によって産生されるCry1A.105タンパク質(国際公開第2007/027777号パンフレット);または
4)標的昆虫種に対するより高い殺虫活性を得るためおよび/または影響を受ける標的昆虫種の範囲を拡大するため、および/またはクローニングもしくは形質転換中にコードDNAに導入される変化により、いくつかの、特に1~10個のアミノ酸が別のアミノ酸によって置き換えられている1)~3)のいずれか1つのタンパク質、例えばトウモロコシイベントMON863もしくはMON88017のCry3Bb1タンパク質、またはトウモロコシイベントMIR604のCry3Aタンパク質;または
5)バチルス・チューリンゲンシス(Bacillus thuringiensis)もしくはバチルス・セレウス(Bacillus cereus)由来の殺虫性分泌タンパク質またはその殺虫性部分、例えばhttp://www.lifesci.sussex.ac.uk/home/Neil_Crickmore/Bt/vip.htmlに列挙されている栄養性殺虫性タンパク質(VIP)、例えばVIP3Aaタンパク質クラスのタンパク質;または
6)バチルス・チューリンゲンシス(Bacillus thuringiensis)またはバチルス・セレウス(B.cereus)由来の第2の分泌タンパク質の存在下で殺虫性となるバチルス・チューリンゲンシス(Bacillus thuringiensis)またはバチルス・セレウス(Bacillus cereus)由来の分泌タンパク質、例えばVIP1AおよびVIP2Aタンパク質で構成される二成分毒素(国際公開第94/21795号パンフレット);または
7)バチルス・チューリンゲンシス(Bacillus thuringiensis)またはバチルス・セレウス(Bacillus cereus)由来の異なる分泌タンパク質の部分を含むハイブリッド殺虫性タンパク質、例えば上記の1)のタンパク質のハイブリッドまたは上記の2)のタンパク質のハイブリッド;または
8)(まだ殺虫性タンパク質をコードするが)標的昆虫種に対するより高い殺虫活性を得るためおよび/または影響を受ける標的昆虫種の範囲を拡大するため、および/またはクローニングもしくは形質転換中にコードDNAで誘導される変化により、いくつかの、特に1~10個のアミノ酸が別のアミノ酸によって置き換えられているポイント5)~7)のいずれか1つのタンパク質、例えばワタイベントCOT102のVIP3Aaタンパク質;または
9)バチルス・チューリンゲンシス(Bacillus thuringiensis)由来の結晶タンパク質の存在下で殺虫性となるバチルス・チューリンゲンシス(Bacillus thuringiensis)またはバチルス・セレウス(Bacillus cereus)由来の分泌タンパク質、例えばタンパク質VIP3およびCry1AもしくはCry1Fで構成される二成分毒素(米国特許出願第61/126083号明細書および同第61/195019号明細書)またはVIP3タンパク質およびCry2AaもしくはCry2AbもしくはCry2Aeタンパク質で構成される二成分毒素(米国特許出願第12/214022号明細書および欧州特許第08010791.5号明細書);または
10)(まだ殺虫性タンパク質をコードするが)標的昆虫種に対するより高い殺虫活性を得るためおよび/または影響を受ける標的昆虫種の範囲を拡大するため、および/またはクローニングもしくは形質転換中にコードDNAで誘導される変化により、いくつかの、特に1~10個のアミノ酸が別のアミノ酸によって置き換えられている上記のポイント9)によるタンパク質。
a.植物細胞または植物でポリ(ADP-リボース)ポリメラーゼ(PARP)遺伝子の発現および/または活性を低下させることができる導入遺伝子を含む植物;
b.植物または植物細胞のPARGコード遺伝子の発現および/または活性を低下させることができるストレス耐性増強導入遺伝子を含む植物;
c.ニコチンアミダーゼ、ニコチン酸ホスホリボシルトランスフェラーゼ、ニコチン酸モノヌクレオチドアデニルトランスフェラーゼ、ニコチンアミドアデニンジヌクレオチドシンテターゼまたはニコチンアミドホスホリボシルトランスフェラーゼを含むニコチンアミドアデニンジヌクレオチドサルベージ生合成経路の植物機能性酵素をコードするストレス耐性増強導入遺伝子を含有する植物。
1)修飾デンプンが特定の用途により適しているようにその物理化学的特性、特にアミロース含量またはアミロース/アミロペクチン比、分岐度、平均鎖長、側鎖分布、粘性挙動、ゲル化強度、デンプン粒径および/またはデンプン粒形態が野生型植物細胞または植物の合成デンプンと比較して変化している修飾デンプンを合成するトランスジェニック植物。
2)非デンプン炭水化物ポリマーを合成する、または遺伝子改変を有さない野生型植物と比較して改変された特性を有する非デンプン炭水化物ポリマーを合成するトランスジェニック植物。例には、特にイヌリンおよびレバン型のポリフルクトースを産生する植物、アルファ-1,4-グルカンを産生する植物、アルファ-1,6-分岐アルファ-1,4-グルカンを産生する植物、ならびにアルテルナンを産生する植物がある。
3)ヒアルロナンを産生するトランスジェニック植物。
4)「高可溶性固形分」、「低辛味」(LP)および/または「長期保存」(LS)などの特定の特性を有するタマネギなどのトランスジェニック植物またはハイブリッド植物。
a)改変型のセルロースシンターゼ遺伝子を含有するワタ植物などの植物、
b)改変型のrsw2またはrsw3相同核酸を含有するワタ植物などの植物、例えばスクロースリン酸シンターゼの発現が増加したワタ植物;
c)スクロースシンターゼの発現が増加したワタ植物などの植物;
d)例えば繊維選択的β-1,3-グルカナーゼの下方制御を通して、繊維細胞を基準とした原形質連絡ゲーティングのタイミングが変化しているワタ植物などの植物;
e)例えばnodCおよびキチンシンターゼ遺伝子を含むN-アセチルグルコサミントランスフェラーゼ遺伝子の発現を通して、反応性が変化した繊維を有するワタ植物などの植物。
a)高オレイン酸含量を有する油を産生するアブラナ植物などの植物;
b)低リノレン酸含量を有する油を産生するアブラナ植物などの植物;
c)低レベルの飽和脂肪酸を有する油を産生するアブラナ植物などの植物。
-請願:請願の識別番号。形質転換事象の技術的説明は、請願番号を介してウェブサイト上でAPHISから入手可能な特定の請願文書に見出すことができる。これらの説明は、これにより参照により開示される。
-請願の延長:範囲または期間の延長が要求されている先の請願の参照。
-機関:請願を提出する人物の名称。
-規制品目:当の植物種。
-トランスジェニック表現型:形質転換事象によって植物に付与される形質。
-形質転換事象または系統:非規制状態が要求されている1つまたは複数の事象(しばしば1つまたは複数の系統とも呼ばれる)の名称。
-APHIS文書:請願に関してAPHISによって公開された、または要求に応じてAPHISから取得することができる様々な文書。
例えば、モニリニア属(Monilinia)種、例えばモニリニア・ラキサ(Monilinia laxa)によって引き起こされる萎凋病;
例えば、タフリナ属(Taphrina)種、例えばタフリナ・デフォルマンス(Taphrina deformans)によって引き起こされる葉、花および果実の変形;
例えば、エスカ(Esca)種、例えばファエモニエラ・クラミドスポラ(Phaemoniella clamydospora)およびファエオアクレモニウム・アレオフィルム(Phaeoacremonium aleophilum)およびフォミチポリア・メジテラネア(Fomitiporia mediterranea)によって引き起こされる木本植物の変性病;例えば、ボトリチス属(Botrytis)種、例えばボトリチス・シネレア(Botrytis cinerea)によって引き起こされる花および種子の病気;例えば、リゾクトニア属(Rhizoctonia)種、例えばリゾクトニア・ソラニ(Rhizoctonia solani);ヘルミントスポリウム属(Helminthosporium)種、例えばヘルミントスポリウム・ソラニ(Helminthosporium solani)によって引き起こされる植物塊茎の病気;細菌病原体、例えばキサントモナス属(Xanthomonas)種、例えばキサントモナス・カンペストリスpv.オリザエ(Xanthomonas campestris pv.oryzae);シュードモナス属(Pseudomonas)種、例えばシュードモナス・シリンガエpv.ラクリマンス(Pseudomonas syringae pv.lachrymans);エルウィニア属(Erwinia)種、例えばエルウィニア・アミロボラ(Erwinia amylovora)によって引き起こされる病気が挙げられる。
例えば、アルテルナリア斑点病(アルテルナリア属(Alternaria)種アトランス・テヌイシマ(atrans tenuissima))、炭そ病(コレトトリカム・グロエオスポロイデス・デマティウム(Colletotrichum gloeosporoides dematium)変種トルンカツム(truncatum))、褐斑病(セプトリア・グリシネス(Septoria glycines))、セレコスポラ葉斑点病および枯れ病(セレコスポラ・キクチイ(Cercospora kikuchii))、コアネフォラ葉枯れ病(コアネフォラ・インファンディブリフェラ・トリスポラ(Choanephora infundibulifera trispora)(同義))、ダクツリオフォラ葉斑点病(ダクツリオフォラ・グリシネス(Dactuliophora glycines))、べと病(ペロノスポラ・マンシュリカ(Peronospora manshurica))、ドレックスレラ胴枯れ病(ドレックスレラ・グリシニ(Drechslera glycini))、フロッグアイ葉斑点病(セルコスポラ・ソジナ(Cercospora sojina))、レプトスファエルリナ葉斑点病(レプトスファエルリナ・トリフォリイ(Leptosphaerulina trifolii))、フィロスチカ葉斑点病(フィロスチカ・ソジェコラ(Phyllosticta sojaecola))、さやおよび茎枯れ病(フォモプシス・ソジャエ(Phomopsis sojae))、うどんこ病(ミクロスファエラ・ディフサ(Microsphaera diffusa))、ピレノケータ葉斑点病(ピレノケータ・グリシネス(Pyrenochaeta glycines))、リゾクトニア・アエリアル(rhizoctonia aerial)、群葉およびクモの巣病(リゾクトニア・ソラニ(Rhizoctonia solani))、さび病(ファコプソラ・パキリジ(Phakopsora pachyrhizi)、ファコプソラ・メイボミアエ(Phakopsora meibomiae))、黒痘病(スファセロマ・グリシネス(Sphaceloma glycines))、ステムフィリウム葉枯れ病(ステムフィリウム・ボトリオスム(Stemphylium botryosum))、輪紋病(コリネスポラ・カッシコラ(Corynespora cassiicola))によって引き起こされる葉、茎、さやおよび種子の真菌病。
1.4-(ジフルオロメチル)-2-メチル-3-[(メチルスルファニル)メチル]-N-(1-メチル-1H-テトラゾール-5-イル)ベンズアミド(実施例番号1-107)の合成
室温(RT)の4-(ジフルオロメチル)-2-メチル-3-[(メチルスルファニル)メチル]安息香酸600mg(2.4mmol)と1-メチル-1H-テトラゾール-5-アミン295.6mg(2.9mmol)のピリジン3ml中初期装入物に、塩化オキサリル0.3ml(3.7mmol)を添加する。反応溶液をRTで12時間攪拌し、次いで、濃縮乾固した。残渣を水10mlに溶解し、ジクロロメタンで抽出した。有機相を硫酸マグネシウム上で乾燥させ、濃縮した。残渣をアセトニトリルに溶解し、カラムクロマトグラフィー(HPLC、C18、勾配:アセトニトリル/水(+0.5%トリフルオロ酢酸)、30分で20/80→100/0)によって精製した。これにより、標的化合物440mgが得られた。
室温(RT)の2-(ジフルオロメチル)-2-メチル-3-[(メチルスルファニル)メチル]安息香酸1.46g(4.43mmol)と1-メチル-1H-テトラゾール-5-アミン538.26mg(5.32mmol)のアセトニトリル15ml中初期装入物に、ピリジン1.8mlを添加する。その後、塩化オキサリル0.58ml(6.65mmol)を添加し、反応混合物をRTで一晩撹拌した。水5mlを添加し、混合物を10分間撹拌し、ジクロロメタンで抽出した。有機相を濃縮し、残渣をカラムクロマトグラフィー(HPLC、C18、勾配:アセトニトリル/水(+0.5%トリフルオロ酢酸)、30分で20/80→100/0)によって精製した。これにより、標的化合物750mgが得られた。
RTの2-ブロモ-3-[(メチルスルファニル)メチル]-N-(1-メチル-1H-テトラゾール-5-イル)-4-(トリフルオロメチル)ベンズアミド(実施例番号1-380)194mg(0.47mmol)の酢酸3ml中初期装入物に、35%過酸化水素水溶液46mg(0.47mmol)を添加した。反応溶液を50℃で2時間攪拌した。溶媒を減圧下で除去し、残渣を水に溶解した。形成した沈殿を濾別し、高真空下で乾燥させた。これにより、標的化合物179mgが得られた。
2-ブロモ-3-[(メチルスルファニル)メチル]-N-(1-メチル-1H-テトラゾール-5-イル)-4-(トリフルオロメチル)ベンズアミド(実施例番号1-380)194mg(0.47mmol)の酢酸3ml中初期装入物に、35%過酸化水素水溶液137mg(0.47mmol)を添加し、触媒量のタングステン酸ナトリウムを添加した。反応溶液を50℃で2時間攪拌した。溶媒を減圧下で除去し、残渣を水に溶解した。形成した沈殿を濾別し、高真空下で乾燥させた。これにより、標的化合物211mgが得られた。
実施例番号1-37:1H-NMR(400.0 MHz,DMSO-d6):δ=11.79(br s,1H);7.99(d,1H);7.78(d,1H);4.38(s,2H);4.03(s,3H);3.42(s,3H);2.58(s,3H);2.22(s,3H).
実施例番号1-38:1H-NMR(400.0 MHz,DMSO-d6):δ=11.83(br s,1H);8.04(d,1H);7.82(d,1H);4.99(d,1H);4.64(d,1H);4.02(s,3H);3.41(s,3H);2.81(s,3H);2.53(s,3H).
実施例番号1-39:1H-NMR(400.0 MHz,DMSO-d6):δ=11.85(br s,1H);8.10(d,1H);7.88(d,1H);5.40(br s,2H);4.02(s,3H);3.40(s,3H);3.18(s,3H);2.58(s,3H).
実施例番号1-46:1H-NMR(400.0 MHz,DMSO-d6):δ=11.59(br s,1H);7.53(d,1H);7.48(d,1H);3.99(s,3H);2.49(s,3H);2.13(s,3H).
実施例番号1-47:1H-NMR(400.0 MHz,DMSO-d6):δ=11.64(br s,1H);7.60(d,1H);7.54(d,1H);4.47(d,1H);4.33(d,1H);3.99(s,3H);2.77(s,3H);2.49(s,3H).
実施例番号1-48:1H-NMR(400.0 MHz,DMSO-d6):δ=11.66(br s,1H);7.64(d,1H);7.56(d,11H);4.90(s,2H);3.99(s,3H);3.16(s,3H);2.54(s,3H).
実施例番号1-74:1H-NMR(400.0 MHz,DMSO-d6):δ=11.58(br s,1H);7.88(d,1H);7.23(d,1H);4.02(s,2H);3.98(s,3H);2.52(s,3H);2.17(s,3H).
実施例番号1-75:1H-NMR(400.0 MHz,DMSO-d6):δ=11.63(br s,1H);7.96(d,1H);7.30(d,1H);4.60(d,1H);4.28(d,1H);3.98(s,3H);2.80(s,3H);2.51(s,3H).
実施例番号1-76:1H-NMR(400.0 MHz,DMSO-d6):δ=11.66(br s,1H);7.98(d,1H);7.33(d,1H);4.94(s,2H);3.99(s,3H);3.17(s,3H);2.57(s,3H).
実施例番号1-83:1H-NMR(400.0 MHz,CDCl3):δ=8.72(br s,1H);7.68(d,1H);7.59(d,1H);4.14(s,3H);3.93(s,2H);2.66(s,3H);2.19(s,3H).
実施例番号1-84:1H-NMR(400.0 MHz,DMSO-d6):δ=11.79(br s,1H);7.80(d,1H);7.76(d,1H);4.54(d,1H);4.21(d,1H);4.01(s,3H);2.81(s,3H);2.55(s,3H).
実施例番号1-85:1H-NMR(400.0 MHz,DMSO-d6):δ=11.82(br s,1H);7.82(s,2H);4.91(br s,2H);4.02(s,3H);3.19(s,3H);2.58(s,3H).
実施例番号1-86:1H-NMR(400.0 MHz,CDCl3):δ=10.64(br s,1H);7.71(d,1H);7.67(d,1H);4.12(s,3H);3.95(s,2H);2.67(m,2H);2.67(s,3H);1.31(t,3H).
実施例番号1-88:1H-NMR(400.0 MHz,DMSO-d6):δ=11.82(br s,1H);7.82(s,2H);4.84(br s,2H);4.02(s,3H);3.33(m,2H);2.58(s,3H);1.33(t,3H).
実施例番号1-107:1H-NMR(400.0 MHz,DMSO-d6):δ=11.63(br s,1H);7.65(d,1H);7.58(d,1H);7.34(t,1H);4.00(s,3H);3.96(s,2H);2.49(s,3H);2.15(s,3H).
実施例番号1-108:1H-NMR(400.0 MHz,DMSO-d6):δ=11.69(br s,1H);7.72(d,1H);7.65(d,1H);7.38(t,1H);4.45(d,1H);4.36(d,1H);2.80(s,3H);2.46(s,3H).
実施例番号1-109:1H-NMR(400.0 MHz,DMSO-d6):δ=11.71(br s,1H);7.77(d,1H);7.69(d,1H);7.33(t,1H);4.94(br s,2H);4.00(s,3H);3.25(s,3H);2.52(s,3H).
実施例番号1-134:1H-NMR(400.0 MHz,CDCl3):δ=10.02(br s,1H);8.07(d,1H);7.64(d,1H);4.12(s,3H);4.10(s,3H);3.96(s,2H);2.25(s,3H).
実施例番号1-135:1H-NMR(400.0 MHz,CDCl3):δ=10.25(br s,1H);8.08(d,1H);7.69(d,1H);4.45(d,1H);4.18(d,1H);4.09(s,3H);4.06(s,3H);2.76(s,3H).
実施例番号1-161:1H-NMR(400.0 MHz,DMSO-d6):δ=11.78(br s,1H);7.91(d,1H);7.76(d,1H);4.19(s,2H);4.06(s,1H);2.46(s,3H);2.22(s,3H).
実施例番号1-162:1H-NMR(400.0 MHz,DMSO-d6):δ=11.83(br s,1H);7.99(d,1H);7.84(d,1H);4.64(d,1H);4.59(d,1H);4.06(s,3H);2.79(s,3H);2.40(s,3H).
実施例番号1-163:1H-NMR(400.0 MHz,DMSO-d6):δ=11.87(br s,1H);8.02(d,1H);7.90(d,1H);5.13(br s,2H);4.06(s,3H);3.22(s,3H);2.38(s,3H).
実施例番号1-170:1H-NMR(400.0 MHz,DMSO-d6):δ=11.71(br s,1H);7.79(d,1H);7.70(d,1H);7.39(t,1H);4.27(s,2H);4.05(s,3H);2.42(s,3H);2.17(s,3H).
実施例番号1-171:1H-NMR(400.0 MHz,DMSO-d6):δ=11.76(br s,1H);7.85(d,1H);7.79(d,1H);7.41(t,1H);4.72(d,1H);4.66(d,1H);4.06(s,3H);2.79(s,3H);2.38(s,3H).
実施例番号1-172:1H-NMR(400.0 MHz,DMSO-d6):δ=11.77(br s,1H);7.89(d,1H);7.83(d,1H);7.38(t,1H);5.25(br s,2H);4.05(s,3H);3.21(s,3H);2.38(s,3H).
実施例番号1-182:1H-NMR(400.0 MHz,DMSO-d6):δ=11.78(br s,1H);7.91(d,1H);7.76(d,1H);4.23(s,2H);4.06(s,3H);2.94(q,2H);2.71(q,2H);1.26(t,3H);1.13(t,3H).
実施例番号1-191:1H-NMR(400.0 MHz,DMSO-d6):δ=11.69(br s,1H);7.78(d,1H);7.69(d,1H);7.38(t,1H);4.32(s,2H);4.05(s,3H);2.92(q,2H);2.66(q,2H);1.26(t,3H);1.13(t,3H).
実施例番号1-199:1H-NMR(400.0 MHz,DMSO-d6):δ=12.08(br s,1H);8.38(d,1H);8.15(d,1H);6.18(d,1H);4.88(d,1H);4.04(s,1H);3.64(s,3H);3.27(s,3H).
実施例番号1-229:1H-NMR(400.0 MHz,DMSO-d6):δ=11.95(br s,1H);8.19(d,1H);8.02(d,1H);7.42(t,1H);3.98(s,3H);3.82(m,2H);3.43(q,2H);1.33(t,3H);1.27(t,3H).
実施例番号1-242:1H-NMR(400.0 MHz,DMSO-d6):δ=9.09(br s,1H);8.14(t,1H);7.67(d,1H);4.09(s,3H);3.96(s,2H);2.22(s,3H).
実施例番号1-244:1H-NMR(400.0 MHz,DMSO-d6):δ=11.95(br s,1H);8.05(t,1H);7.87(d,1H);4.81(s,2H);3.99(s,3H);3.22(s,3H).
実施例番号1-278:1H-NMR(400.0 MHz,CDCl3):δ=8.18(d,1H);7.69(d,1H);4.53(s,2H);4.45(s,3H);3.38(s,3H);2.28(s,3H).
実施例番号1-280:1H-NMR(400.0 MHz,DMSO-d6):δ=12.06(br s,1H);8.24(d,1H);8.06(d,1H);5.43(br s,2H);4.03(s,3H);3.45(s,3H);3.22(s,3H).
実施例番号1-287:1H-NMR(400.0 MHz,DMSO-d6):δ=7.51(d,1H);7.26(d,1H);3.95(s,2H);2.45(s,3H);2.11(s,3H).
実施例番号1-288:1H-NMR(400.0 MHz,DMSO-d6):δ=11.74(br s,1H);7.58(d,1H);7.38(d,1H);4.41(d,1H);4.32(d,1H);3.99(s,3H);2.77(s,3H).
実施例番号1-289:1H-NMR(400.0 MHz,DMSO-d6):δ=11.75(br s,1H);7.62(d,1H);7.41(d,1H);4.85(s,2H);3.99(s,3H);3.15(s,3H);2.54(s,3H).
実施例番号1-296:1H-NMR(400.0 MHz,CDCl3):δ=9.38(br s,1H);7.76(d,1H);7.69(d,1H);4.14(s,3H);4.05(s,2H);2.24(s,3H).
実施例番号1-297:1H-NMR(400.0 MHz,DMSO-d6):δ=12.02(br s,1H);7.96(m,2H);4.48(d,1H);4.42(d,1H);4.03(s,3H);2.81(s,3H).
実施例番号1-298:1H-NMR(400.0 MHz,DMSO-d6):δ=12.04(br s,1H);8.00(s,2H);4.98(br s,2H);4.03(s,3H);3.24(s,3H).
実施例番号1-299:1H-NMR(400.0 MHz,DMSO-d6):δ=11.97(br s,1H);7.90(d,1H);7.86(d,1H);4.04(s,2H);4.02(s,3H);2.72(q,2H);1.25(t,3H).
実施例番号1-300:1H-NMR(400.0 MHz,DMSO-d6):δ=12.02(br s,1H);7.98(d,1H);7.94(d,1H);4.43(d,1H);4.38(d,1H);4.02(s,3H);3.08(m,1H);2.94(m,1H);1.29(t,3H).
実施例番号1-301:1H-NMR(400.0 MHz,CDCl3):δ=9.81(br s,1H);7.85(d,1H);7.80(d,1H);4.85(s,2H);4.12(s,3H);3.21(q,2H);1.50(t,3H).
実施例番号1-302:1H-NMR(400.0 MHz,DMSO-d6):δ=11.97(br s,1H);7.90(d,1H);7.86(d,1H);4.13(s,2H);4.02(s,3H);2.10(m,1H);0.89(m,2H);0.49(m,2H).
実施例番号1-303:1H-NMR(400.0 MHz,DMSO-d6):δ=12.02(br s,1H);7.98(d,1H);7.94(d,1H);4.55(d,1H);4.48(d,1H);4.02(s,3H);2.67(m,1H);0.99(m,2H);0.68(m,2H).
実施例番号1-304:1H-NMR(400.0 MHz,DMSO-d6):δ=12.04(br s,1H);8.00(s,2H);5.00(s,2H);4.03(s,3H);2.96(m,1H);1.11(m,2H);1.05(m,2H).
実施例番号1-305:1H-NMR(400.0 MHz,DMSO-d6):δ=11.97(br s,1H);7.92(d,1H);7.88(d,1H);4.11(s,2H);4.02(s,3H);3.57(t,2H);3.28(s,3H);2.88(t,2H).
実施例番号1-306:1H-NMR(400.0 MHz,DMSO-d6):δ=12.01(br s,1H);7.97(d,1H);7.94(d,1H);4.55(d,1H);4.46(d,1H);4.02(s,3H);3.81(m,1H);3.75(m,1H);3.33(m,1H);3.31(s,3H);3.17(m,1H).
実施例番号1-307:1H-NMR(400.0 MHz,DMSO-d6):δ=12.05(br s,1H);7.99(s,2H);5.00(br s,2H);4.03(s,3H);3.80(t,2H);3.63(t,2H);3.35(s,3H).
実施例番号1-308:1H-NMR(400.0 MHz,DMSO-d6):δ=11.96(br s,1H);7.90(d,1H);7.86(d,1H);5.87(m,1H);5.26(d,1H);5.85(d,1H);4.02(s,3H);3.96(s,2H);3.38(d,2H).
実施例番号1-311:1H-NMR(400.0 MHz,DMSO-d6):δ=11.99(br s,1H);7.93(m,2H);4.26(s,2H);4.03(s,3H);3.75(q,2H).
実施例番号1-312:1H-NMR(400.0 MHz,DMSO-d6):δ=12.03(br s,1H);8.00(s,2H);4.80(d,1H);4.61(d,1H);4.49(m,1H);4.29(m,1H);4.03(s,3H).
実施例番号1-313:1H-NMR(400.0 MHz,DMSO-d6):δ=12.05(br s,1H);8.03(m,2H);5.13(br s,2H);4.98(q,2H);4.03(s,3H).
実施例番号1-314:1H-NMR(400.0 MHz,DMSO-d6):δ=11.97(br s,1H);7.90(d,1H);7.85(d,1H);4.10(s,2H);4.02(s,3H);2.67(d,2H);1.02(m,1H);0.55(m,2H);0.24(m,2H).
実施例番号1-315:1H-NMR(400.0 MHz,DMSO-d6):δ=12.02(br s,1H);7.97(d,1H);7.94(d,1H);4.50(d,1H);4.44(d,1H);4.02(s,3H);3.00(m,2H);1.14(m,1H);0.65(m,2H);0.47(m,1H);0.38(m,1H).
実施例番号1-316:1H-NMR(400.0 MHz,DMSO-d6):δ=12.05(br s,1H);8.00(s,2H);4.94(br s,2H);4.03(s,3H);3.34(d,2H);1.18(m,1H);0.69(m,2H);0.48(m,2H).
実施例番号1-317:1H-NMR(400.0 MHz,DMSO-d6):δ=11.96(br s,1H);7.89(d,1H);7.85(d,1H);4.04(s,2H);4.02(s,3H);3.18(m,1H);1.29(d,6H).
実施例番号1-320:1H-NMR(400.0 MHz,DMSO-d6):δ=11.90(br s,1H);7.80(d,1H);7.75(d,1H);7.38(t,1H);4.07(s,2H);4.01(s,3H);2.14(s,3H).
実施例番号1-321:1H-NMR(400.0 MHz,DMSO-d6):δ=11.93(br s,1H);7.90(d,1H);7.82(d,1H);7.39(t,1H);4.54(s,2H);4.02(s,3H);2.79(s,3H).
実施例番号1-322:1H-NMR(400.0 MHz,DMSO-d6):δ=11.94(br s,1H);7.94(d,1H);7.86(d,1H);7.35(t,1H);5.07(s,2H);4.02(s,3H);3.24(s,3H).
実施例番号1-323:1H-NMR(400.0 MHz,DMSO-d6):δ=11.89(br s,1H);7.79(d,1H);7.74(d,1H);7.36(t,1H);4.09(s,2H);4.01(s,3H);2.65(q,2H);1.23(t,3H).
実施例番号1-324:1H-NMR(400.0 MHz,DMSO-d6):δ=11.97(br s,1H);7.89(d,1H);7.82(d,1H);7.38(t,1H);4.49(s,2H);4.02(s,3H);3.09(m,1H);2.97(m,1H);1.29(t,3H).
実施例番号1-325:1H-NMR(400.0 MHz,DMSO-d6):δ=11.95(br s,1H);7.94(d,1H);7.86(d,1H);7.32(t,1H);5.01(s,2H);4.02(s,3H);3.38(q,2H);1.33(t,3H).
実施例番号1-326:1H-NMR(400.0 MHz,DMSO-d6):δ=11.89(br s,1H);7.79(d,1H);7.74(d,1H);7.39(t,1H);4.16(s,2H);4.01(s,3H);2.01(m,1H);0.84(m,2H);0.44(m,2H).
実施例番号1-327:1H-NMR(400.0 MHz,DMSO-d6):δ=11.92(br s,1H);7.87(d,1H);7.80(d,1H);7.37(t,1H);4.59(q,2H);4.01(s,3H);2.61(m,1H);0.96(m,3H);0.67(m,1H).
実施例番号1-328:1H-NMR(400.0 MHz,DMSO-d6):δ=11.92(br s,1H);7.94(d,1H);7.85(d,1H);7.36(t,1H);5.08(s,2H);4.02(s,3H);2.92(m,1H);1.09(m,2H);1.02(m,2H).
実施例番号1-335:1H-NMR(400.0 MHz,DMSO-d6):δ=11.90(br s,1H);7.84(d,1H);7.76(d,1H);7.35(t,1H);4.28(s,2H);4.02(s,3H);3.71(q,2H).
実施例番号1-336:1H-NMR(400.0 MHz,DMSO-d6):δ=11.56(br s,1H);7.93(d,1H);7.84(d,1H);7.36(t,1H);4.89(d,1H);4.67(d,1H);4.45(m,1H);4.34(m,1H);4.02(s,3H).
実施例番号1-337:1H-NMR(400.0 MHz,DMSO-d6):δ=11.97(br s,1H);7.99(d,1H);7.89(d,1H);7.28(t,1H);5.20(s,2H);5.022(q,2H);4.02(s,3H).
実施例番号1-338:1H-NMR(400.0 MHz,DMSO-d6):δ=11.91(br s,1H);7.79(d,1H);7.74(d,1H);7.37(t,1H);4.14(s,2H);4.02(s,3H);2.62(d,2H);1.01(m,1H);0.54(m,2H);0.22(m,2H).
実施例番号1-339:1H-NMR(400.0 MHz,DMSO-d6):δ=11.94(br s,1H);7.88(d,1H);7.81(d,1H);7.38(t,1H);4.55(d,1H);4.50(d,1H);4.02(s,3H);3.02(m,2H);1.12(m,1H);0.65(m,2H);0.44(m,1H);0.39(m,1H).
実施例番号1-340:1H-NMR(400.0 MHz,DMSO-d6):δ=11.96(br s,1H);7.94(d,1H);7.86(d,1H);7.31(t,1H);5.01(s,2H);4.02(s,3H);3.38(d,2H);1.19(m,1H);0.70(m,2H);0.48(m,2H).
実施例番号1-353:1H-NMR(400.0 MHz,DMSO-d6):δ=11.84(br s,1H);7.82(d,1H);7.57(d,1H);4.07(s,2H);4.00(s,3H);2.17(s,3H).
実施例番号1-354:1H-NMR(400.0 MHz,DMSO-d6):δ=11.88(br s,1H);7.88(d,1H);7.65(d,1H);4.56(d,1H);4.48(d,1H);4.00(s,3H);2.78(s,3H).
実施例番号1-355:1H-NMR(400.0 MHz,DMSO-d6):δ=11.91(br s,1H);7.90(d,1H);7.69(d,1H);4.97(s,2H);4.00(s,3H);3.19(s,3H).
実施例番号1-356:1H-NMR(400.0 MHz,DMSO-d6):δ=11.86(br s,1H);7.81(d,1H);7.57(d,1H);4.09(s,2H);4.00(s,3H);2.66(q,2H);1.25(t,3H).
実施例番号1-357:1H-NMR(400.0 MHz,DMSO-d6):δ=11.90(br s,1H);7.87(d,1H);7.65(d,1H);4.51(d,1H);4.43(d,1H);4.00(s,3H);3.02(m,1H);2.92(m,1H);1.30(t,3H).
実施例番号1-358:1H-NMR(400.0 MHz,DMSO-d6):δ=11.91(br s,1H);7.90(d,1H);7.69(d,1H);4.92(br s,2H);4.00(s,3H);3.32(q,2H);1.33(t,3H).
実施例番号1-362:1H-NMR(400.0 MHz,DMSO-d6):δ=11.81(br s,1H);8.03(d,1H);7.35(d,1H);4.10(s,2H);3.99(s,3H);2.19(s,3H).
実施例番号1-363:1H-NMR(400.0 MHz,DMSO-d6):δ=11.85(br s,1H);8.09(d,1H);7.43(d,1H);4.59(d,1H);4.52(d,1H);3.99(s,3H);2.79(s,3H).
実施例番号1-364:1H-NMR(400.0 MHz,DMSO-d6):δ=11.87(br s,1H);8.11(d,1H);4.99(s,2H);4.00(s,3H);3.19(s,3H).
実施例番号1-380:1H-NMR(400.0 MHz,DMSO-d6):δ=12.00(br s,1H);7.94(d,1H);7.81(d,1H);4.05(s,5H);2.24(s,3H).
実施例番号1-381:1H-NMR(400.0 MHz,DMSO-d6):δ=11.94(br s,1H);8.00(d,1H);7.88(d,1H);4.48(q,2H);4.04(s,3H);2.81(s,3H).
実施例番号1-382:1H-NMR(400.0 MHz,DMSO-d6):δ=11.99(br s,1H);8.01(d,1H);7.91(d,1H);5.01(br s,2H);4.03(s,3H);3.25(s,3H).
実施例番号1-383:1H-NMR(400.0 MHz,DMSO-d6):δ=11.96(br s,1H);7.93(d,1H);7.80(d,1H);4.07(s,2H);4.04(s,3H);2.73(q,2H);1.26(t,3H).
実施例番号1-384:1H-NMR(400.0 MHz,DMSO-d6):δ=12.02(br s,1H);8.00(d,1H);7.89(d,1H);4.46(d,1H);4.40(d,1H);4.04(s,3H);3.09(m,1H);2.97(m,1H);1.30(t,3H).
実施例番号1-385:1H-NMR(400.0 MHz,DMSO-d6):δ=12.03(br s,1H);7.98(d,1H);7.87(d,1H);4.94(br s,2H);3.99(s,3H);3.36(q,2H);1.34(t,3H).
実施例番号1-404:1H-NMR(400.0 MHz,DMSO-d6):δ=11.88(br s,1H);7.78(d,11H);7.74(d,1H);7.38(t,11H);4.09(s,2H);4.02(s,3H);2.16(s,3H).
実施例番号1-405:1H-NMR(400.0 MHz,DMSO-d6):δ=11.93(br s,1H);7.84(br s,2H);7.40(t,1H);4.58(d,1H);4.52(d,1H);4.04(s,3H);2.81(s,3H).
実施例番号1-406:1H-NMR(400.0 MHz,DMSO-d6):δ=11.93(br s,1H);7.88(br s,2H);7.36(t,1H);5.09(br s,2H);4.04(s,3H);3.24(s,3H).
実施例番号1-407:1H-NMR(400.0 MHz,DMSO-d6):δ=11.88(br s,1H);7.77(d,1H);7.73(d,1H);7.36(t,1H),4.10(s,2H);4.03(s,3H);2.67(q,2H);1.24(t,3H).
実施例番号1-408:1H-NMR(400.0 MHz,DMSO-d6):δ=11.93(br s,1H);7.84(br s,2H);7.37(t,1H);4.55(d,1H);4.48(d,1H);4.04(s,3H);3.09(m,1H);2.99(m,1H);1.30(t,3H).
実施例番号1-409:1H-NMR(400.0 MHz,DMSO-d6):δ=11.96(br s,1H);7.88(s,2H);7.33(t,1H);5.04(s,2H);4.04(s,3H);3.38(q,2H);1.34(t,3H).
実施例番号1-487:1H-NMR(400.0 MHz,DMSO-d6):δ=11.67(br s,1H);7.67(d,1H);7.60(d,1H);7.36(t,1H);4.00(s,3H);3.95(s,2H);2.89(q,2H);2.19(s,3H);1.22(t,3H).
実施例番号1-490:1H-NMR(400.0 MHz,DMSO-d6):δ=11.76(br s,1H);7.73(m,2H);4.01(s,3H);3.95(s,2H);2.98(q,2H);2.70(q,2H);1.26(m,6H).
実施例番号1-493:1H-NMR(400.0 MHz,DMSO-d6):δ=11.76(br s,1H);7.73(m,2H);4.01(s,2H);4.01(s,3H);2.97(q,2H);2.10(m,1H);1.24(t,3H);0.90(m,2H);0.51(m,2H).
実施例番号1-494:1H-NMR(400.0 MHz,DMSO-d6):δ=11.83(br s,1H);7.83(d,1H);7.79(d,1H);4.48(d,1H);4.29(d,1H);3.20(m,1H);2.82(m,1H);2.72(m,1H);1.18(t,3H);1.03(m,3H);0.69(m,1H).
実施例番号1-495:1H-NMR(400.0 MHz,DMSO-d6):δ=11.89(br s,1H);7.84(m,2H);4.88(br s,2H);4.02(s,3H);3.07(br s,1H);2.95(m,1H);1.16(t,3H);1.10(m,2H);1.02(m,2H).
実施例番号1-497:1H-NMR(400.0 MHz,DMSO-d6):δ=11.72(br s,1H);7.74(d,1H);7.66(d,1H);7.41(t,1H);4.41(d,1H);4.33(d,1H);4.01(s,3H);2.98(m,1H);2.48(s,3H);2.81(m,1H);1.17(t,3H).
実施例番号1-498:1H-NMR(400.0 MHz,DMSO-d6):δ=11.75(br s,1H);7.79(d,1H);7.70(d,1H);7.34(t,1H);4.89(s,2H);4.01(s,3H);3.29(s,3H);2.93(br q,2H);1.15(t,3H).
実施例番号1-514:1H-NMR(400.0 MHz,DMSO-d6):δ=11.69(br s,1H);7.75(d,1H);7.64(d,1H);4.18(s,2H);4.04(s,3H);2.29(m,1H);2.18(s,3H);1.11(m,2H);0.64(m,2H).
実施例番号1-515:1H-NMR(400.0 MHz,DMSO-d6):δ=11.75(br s,1H);7.83(d,1H);7.73(d,1H);4.70(d,1H);4.42(d,2H);4.04(s,3H);2.78(s,3H);2.25(m,1H);1.15(m,2H);0.61(m,2H).
実施例番号1-516:1H-NMR(400.0 MHz,DMSO-d6):δ=11.79(br s,1H);7.87(d,1H);7.80(m,1H);5.32(br s,1H);4.79(br s,1H);4.04(s,3H);3.19(s,3H);2.32(m,1H);1.17(br s,2H);0.58(br s,2H).
実施例番号1-517:1H-NMR(400.0 MHz,DMSO-d6):δ=11.70(br s,1H);7.77(d,1H);7.65(d,1H);4.22(s,2H);4.04(s,3H);2.69(q,2H);2.28(m,1H);1.26(t,3H);1.11(m,2H);0.66(d,2H).
実施例番号1-518:1H-NMR(400.0 MHz,DMSO-d6):δ=11.75(br s,1H);7.83(d,1H);7.73(d,1H);4.68(d,1H);4.37(d,1H);4.04(s,3H);3.03(m,1H);2.92(m,1H);2.25(m,1H);1.29(t,3H);1.11(m,2H);0.61(m,2H).
実施例番号1-519:1H-NMR(400.0 MHz,DMSO-d6):δ=11.77(br s,1H);7.86(d,1H);7.80(d,1H);5.28(br s,1H);4.70(br s,1H);4.04(s,3H);3.32(q,2H);2.34(m,1H);1.32(t,3H);1.14(br s,2H);0.58(br s,2H).
実施例番号1-523:1H-NMR(400.0 MHz,DMSO-d6):δ=11.60(br s,1H);7.38(t,1H);4.20(s,2H);4.03(s,3H);2.17(s,3H);2.16(m,1H);1.06(m,2H);0.64(m,2H).
実施例番号1-524:1H-NMR(400.0 MHz,DMSO-d6):δ=11.66(br s,1H);7.68(br s,2H);7.42(t,1H);4.60(s,2H);4.03(s,3H);2.80(s,3H);2.09(m,1H);1.09(m,2H);0.59(m,2H).
実施例番号1-525:1H-NMR(400.0 MHz,DMSO-d6):δ=11.70(br s,1H);7.73(br s,1H);7.35(t,1H);5.11(br s,2H);4.03(s,3H);3.25(s,3H);2.23(m,1H);1.13(m,2H);0.57(m,2H).
実施例番号1-552:1H-NMR(400.0 MHz,DMSO-d6):δ=12.05(br s,1H);8.37(d,1H);8.14(br s,1H);5.01(d,1H);4.85(d,1H);4.01(s,3H);3.21(s,3H).
実施例番号1-559:1H-NMR(400.0 MHz,CDCl3):δ=10.71(br s,1H);7.58(d,1H);7.50(d,1H);4.11(s,3H);4.09(s,2H);2.19(s,3H).
実施例番号1-561:1H-NMR(400.0 MHz,DMSO-d6):δ=11.91(br s,1H);7.90(d,1H);7.75(d,1H);4.94(s,2H);4.00(s,3H);3.19(s,3H).
実施例番号1-568:1H-NMR(400.0 MHz,DMSO-d6):δ=12.02(br s,1H);7.98(d,1H);7.94(d,1H);4.48(d,1H);4.42(d,1H);4.03(s,3H);2.81(s,3H).
実施例番号1-569:1H-NMR(400.0 MHz,DMSO-d6):δ=12.02(br s,1H);7.98(d,1H);7.94(d,1H);4.49(d,1H);4.42(d,1H);4.03(s,3H);2.81(s,3H).
実施例番号1-570:1H-NMR(400.0 MHz,CDCl3):δ=10.09(br s,1H);7.97(d,1H);7.41(d,1H);4.10(s,3H);4.08(s,3H);3.95(s,2H);2.22(s,3H).
実施例番号1-571:1H-NMR(400.0 MHz,CDCl3):δ=8.01(d,1H);7.46(d,1H);4.41(d,1H);4.24(d,1H);4.09(s,3H);4.07(s,3H);2.76(s,3H).
実施例番号1-572:1H-NMR(400.0 MHz,CDCl3):δ=9.95(br s,1H);8.03(d,1H);7.49(d,1H);4.68(s,2H);4.09(s,3H);4.07(s,3H);3.03(s,3H).
実施例番号2-37:1H-NMR(400.0 MHz,DMSO-d6):δ=11.67(br s,1H);7.98(d,1H);7.75(d,1H);4.36(m,4H);3.40(s,3H);2.56(s,3H);2.20(s,3H);1.48(t,3H).
実施例番号2-39:1H-NMR(400.0 MHz,DMSO-d6):δ=11.75(br s,1H);8.11(d,1H);7.87(d,1H);5.41(br s,2H);4.37(q,2H);3.40(s,3H);3.19(s,3H);2.58(s,3H);1.48(t,3H).
実施例番号2-46:1H-NMR(400.0 MHz,DMSO-d6):δ=11.49(br s,1H);7.52(d,1H);7.48(d,1H);4.34(q,2H);3.98(s,2H);2.49(s,3H);2.13(s,3H);1.47(t,3H).
実施例番号2-47:1H-NMR(400.0 MHz,DMSO-d6):δ=11.53(br s,1H);7.59(d,1H);7.54(d,1H);4.47(d,1H);4.34(m,3H);2.77(s,3H);2.50(s,3H);1.47(t,3H).
実施例番号2-48:1H-NMR(400.0 MHz,DMSO-d6):δ=11.56(br s,1H);7.63(d,1H);7.56(d,1H);4.90(s,2H);4.34(q,2H);3.16(s,3H);2.54(s,3H);1.47(t,3H).
実施例番号2-74:1H-NMR(400.0 MHz,DMSO-d6):δ=11.48(br s,1H);7.89(d,1H);7.22(d,1H);4.33(q,2H);4.03(s,2H);2.52(s,3H);2.17(s,3H);1.46(t,3H).
実施例番号2-75:1H-NMR(400.0 MHz,DMSO-d6):δ=11.53(br s,1H);7.96(d,1H);7.28(d,1H);4.60(d,1H);4.33(q,2H);4.28(d,1H);2.80(s,3H);2.51(s,3H);1.46(t,3H).
実施例番号2-76:1H-NMR(400.0 MHz,DMSO-d6):δ=11.55(br s,1H);7.98(d,1H);7.32(d,1H);4.94(br s,2H);4.33(q,2H);3.17(s,3H);2.57(s,3H);1.47(t,3H).
実施例番号2-86:1H-NMR(400.0 MHz,CDCl3):δ=10.62(br s,1H);7.67(m,2H);4.50(q,2H);3.94(s,2H);2.67(s,3H);2.65(m,2H);1.63(t,3H);1.31(t,3H).
実施例番号2-88:1H-NMR(400.0 MHz,DMSO-d6):δ=11.72(br s,1H);7.82(m,2H);4.84(br s,2H);4.36(q,2H);3.33(m,2H);2.58(s,3H);1.48(t,3H);1.33(t,3H).
実施例番号2-107:1H-NMR(400.0 MHz,DMSO-d6):δ=11.55(br s,1H);7.64(d,1H);7.59(d,1H);7.34(t,1H);4.35(q,2H);3.96(s,3H);2.49(s,3H);2.15(s,3H);1.48(t,3H).
実施例番号2-108:1H-NMR(400.0 MHz,DMSO-d6):δ=11.59(br s,1H);7.71(d,1H);7.65(d,1H);7.38(t,1H);4.45(d,1H);4.36(m,3H);2.80(s,3H);2.46(s,3H);1.48(t,3H).
実施例番号2-109:1H-NMR(400.0 MHz,DMSO-d6):δ=11.60(br s,1H);7.76(d,1H);7.69(d,1H);7.33(t,1H);4.94(s,2H);4.35(q,2H);3.25(s,3H);2.52(s,3H);1.48(t,3H).
実施例番号2-134:1H-NMR(400.0 MHz,CDCl3):δ=9.99(br s,1H);8.07(d,1H);7.64(d,1H);4.44(q,2H);4.12(s,3H);3.96(s,2H);2.25(s,3H);1.62(t,3H).
実施例番号2-136:1H-NMR(400.0 MHz,CDCl3):δ=9.93(br s,1H);8.13(d,1H);7.71(d,1H);4.71(s,2H);4.43(q,2H);3.98(s,3H);3.06(s,3H);1.63(t,3H).
実施例番号2-161:1H-NMR(400.0 MHz,DMSO-d6):δ=11.67(br s,1H);7.91(d,1H);7.75(d,1H);4.43(q,2H);4.19(s,2H);2.46(s,3H);2.22(s,3H);1.50(t,3H).
実施例番号2-162:1H-NMR(400.0 MHz,DMSO-d6):δ=11.73(br s,1H);7.99(d,1H);7.83(d,1H);4.64(d,1H);4.56(d,1H);4.44(q,2H);2.79(s,3H);2.40(s,3H);1.50(t,3H).
実施例番号2-163:1H-NMR(400.0 MHz,DMSO-d6):δ=11.76(br s,1H);8.02(d,1H);7.89(d,1H);5.14(br s,2H);4.44(q,2H);3.23(s,3H);2.39(s,3H);1.50(t,3H).
実施例番号2-170:1H-NMR(400.0 MHz,DMSO-d6):δ=11.60(br s,1H);7.79(d,1H);7.68(d,1H);7.39(t,1H);4.43(q,2H);4.27(s,2H);2.43(s,3H);2.17(s,3H);1.49(t,3H).
実施例番号2-171:1H-NMR(400.0 MHz,DMSO-d6):δ=11.65(br s,1H);7.86(d,1H);7.78(d,1H);7.41(t,1H);4.72(d,1H);4.66(d,1H);4.44(q,2H);2.80(s,3H);2.38(s,3H);1.50(t,3H).
実施例番号2-172:1H-NMR(400.0 MHz,DMSO-d6):δ=11.67(br s,1H);7.90(d,1H);7.83(d,1H);7.38(t,1H);5.25(br s,2H);4.43(q,2H);3.22(s,3H);2.38(s,3H);1.50(t,3H).
実施例番号2-278:1H-NMR(400.0 MHz,CDCl3):δ=10.5(br s,1H);8.15(d,1H);7.69(d,1H);4.52(m,4H);3.38(s,3H);2.28(s,3H);1.65(t,3H).
実施例番号2-280:1H-NMR(400.0 MHz,CDCl3):δ=10.61(br s,1H);8.17(d,1H);7.85(d,1H);4.46(q,2H);3.34(s,3H);3.14(s,3H);1.62(t,3H).
実施例番号2-287:1H-NMR(400.0 MHz,DMSO-d6):δ=11.59(br s,1H);7.49(d,1H);7.34(d,1H);4.35(q,2H);3.96(d,2H);2.48(s,3H);2.13(s,3H);1.47(t,3H).
実施例番号2-288:1H-NMR(400.0 MHz,DMSO-d6):δ=11.65(br s,1H);7.56(d,1H);7.38(d,1H);4.36(m,4H);2.77(s,3H);1.47(t,3H).
実施例番号2-289:1H-NMR(400.0 MHz,DMSO-d6):δ=11.65(br s,1H);7.61(d,1H);7.41(d,1H);4.85(s,3H);4.36(q,2H);3.15(s,3H);2.54(s,3H);1.47(t,3H).
実施例番号2-296:1H-NMR(400.0 MHz,CDCl3):δ=10.10(br s,1H);7.75(d,1H);7.68(d,1H);4.50(q,2H);4.05(s,3H);2.22(s,3H);1.64(t,3H).
実施例番号2-297:1H-NMR(400.0 MHz,DMSO-d6):δ=11.92(br s,1H);7.97(d,1H);7.93(d,1H);4.48(d,1H);4.43(d,1H);4.38(q,2H);2.81(s,3H);1.48(t,3H).
実施例番号2-298:1H-NMR(400.0 MHz,DMSO-d6):δ=11.94(br s,1H);8.00(s,2H);4.98(br s,2H);4.39(q,2H);3.24(s,3H);1.49(t,3H).
実施例番号2-299:1H-NMR(400.0 MHz,DMSO-d6):δ=11.88(br s,1H);7.90(d,1H);7.85(d,1H);4.38(q,2H);4.04(s,2H);2.72(q,2H);1.48(t,3H);1.25(t,3H).
実施例番号2-300:1H-NMR(400.0 MHz,DMSO-d6):δ=11.92(br s,1H);7.97(d,1H);7.93(d,1H);4.40(m,4H);3.09(m,1H);2.95(m,1H);1.48(t,3H);1.30(t,3H).
実施例番号2-301:1H-NMR(400.0 MHz,CDCl3):δ=9.91(br s,1H);7.83(d,1H);7.80(d,1H);4.84(s,2H);4.47(q,2H);3.21(q,2H);1.63(t,3H);1.49(t,3H).
実施例番号2-302:1H-NMR(400.0 MHz,DMSO-d6):δ=11.88(br s,1H);7.90(d,1H);7.85(d,1H);4.38(q,2H);4.13(s,2H);2.10(m,1H);1.48(t,3H);0.88(m,2H);0.49(m,2H).
実施例番号2-303:1H-NMR(400.0 MHz,DMSO-d6):δ=11.92(br s,1H);7.98(d,1H);7.93(d,1H);4.55(d,1H);4.48(d,1H);4.38(q,2H);2.67(m,1H);1.48(t,3H);1.01(m,3H);0.68(m,1H).
実施例番号2-304:1H-NMR(400.0 MHz,DMSO-d6):δ=11.93(br s,1H);8.00(s,2H);5.00(br s,2H);4.37(q,2H);2.95(m,1H);1.49(t,3H);1.11(m,2H);1.05(m,2H).
実施例番号2-305:1H-NMR(400.0 MHz,DMSO-d6):δ=11.87(br s,1H);7.90(d,1H);7.85(d,1H);4.38(q,2H);4.11(s,2H);3.57(t,2H);3.28(s,3H);2.88(t,2H);1.48(t,3H).
実施例番号2-306:1H-NMR(400.0 MHz,DMSO-d6):δ=11.92(br s,1H);7.97(d,1H);7.93(d,1H);4.55(d,1H);4.47(d,1H);4.38(q,2H);3.82(m,1H);3.73(m,1H);3.34(m,1H);3.31(s,3H);3.18(m,1H);1.48(t,3H).
実施例番号2-307:1H-NMR(400.0 MHz,DMSO-d6):δ=11.94(br s,1H);7.99(s,2H);5.00(br s,2H);4.38(q,2H);3.81(t,2H);3.63(t,2H);3.35(s,3H);1.49(t,3H).
実施例番号2-308:1H-NMR(400.0 MHz,DMSO-d6):δ=11.86(br s,1H);7.90(d,1H);7.85(d,1H);5.87(m,1H);5.25(d,1H);5.17(d,1H);4.38(q,2H);3.96(s,2H);3.38(d,2H);1.48(t,3H).
実施例番号2-311:1H-NMR(400.0 MHz,DMSO-d6):δ=11.89(br s,1H);7.93(m,2H);4.38(q,2H);4.26(s,2H);3.76(q,2H);1.48(t,3H).
実施例番号2-314:1H-NMR(400.0 MHz,DMSO-d6):δ=11.87(br s,1H);7.89(d,1H);7.84(d,1H);4.38(q,2H);4.10(s,2H);2.68(d,2H);1.48(t,3H);1.02(m,1H);0.55(m,2H);0.24(m,2H).
実施例番号2-315:1H-NMR(400.0 MHz,DMSO-d6):δ=11.92(br s,1H);7.97(d,1H);7.93(d,1H);4.49(d,1H);4.44(d,1H);4.38(q,2H);3.01(d,2H);1.48(t,3H);1.14(m,1H);0.66(m,2H);0.39(m,1H).
実施例番号2-316:1H-NMR(400.0 MHz,DMSO-d6):δ=11.95(br s,1H);4.94(br s,2H);4.38(q,2H);3.34(d,2H);1.49(t,3H);1.18(m,1H);0.69(m,2H);0.48(m,2H).
実施例番号2-320:1H-NMR(400.0 MHz,DMSO-d6):δ=11.79(br s,1H);7.79(d,1H);7.75(d,1H);7.38(t,1H);4.37(q,2H);4.07(s,2H);2.15(s,3H);1.48(t,3H).
実施例番号2-321:1H-NMR(400.0 MHz,DMSO-d6):δ=11.88(br s,1H);7.89(d,1H);7.81(d,1H);7.39(t,1H);4.54(s,2H);4.38(q,2H);2.79(s,3H);1.49(t,3H).
実施例番号2-322:1H-NMR(400.0 MHz,DMSO-d6):δ=11.84(br s,1H);7.93(d,1H);7.84(d,1H);7.35(t,1H);5.07(s,2H);4.38(q,2H);3.24(s,3H);1.48(t,3H).
実施例番号2-323:1H-NMR(400.0 MHz,DMSO-d6):δ=11.79(br s,1H);7.78(d,1H);7.74(d,1H);7.36(t,1H);4.37(q,2H);4.09(s,2H);2.65(q,2H);1.48(t,3H);1.23(t,3H).
実施例番号2-324:1H-NMR(400.0 MHz,DMSO-d6):δ=11.85(br s,1H);7.88(d,1H);7.81(d,1H);7.37(t,1H);4.49(s,2H);4.38(q,2H);3.09(m,1H);2.98(m,1H);1.48(t,3H);1.29(t,3H).
実施例番号2-325:1H-NMR(400.0 MHz,DMSO-d6):δ=11.85(br s,1H);7.93(d,1H);7.85(d,1H);7.32(t,1H);5.02(s,2H);4.38(q,2H);3.38(q,2H);1.48(t,3H);1.34(t,3H).
実施例番号2-338:1H-NMR(400.0 MHz,DMSO-d6):δ=11.82(br s,1H);7.79(d,1H);7.74(d,1H);7.37(t,1H);4.38(q,2H);4.14(s,2H);2.62(d,2H);1.48(t,3H);1.02(m,1H);0.54(m,2H);0.22(m,2H).
実施例番号2-339:1H-NMR(400.0 MHz,DMSO-d6):δ=11.84(br s,1H);7.88(d,1H);7.81(d,1H);7.38(t,1H);4.55(d,1H);4.50(d,1H);4.38(q,2H);3.02(m,2H);1.48(t,3H);1.12(m,1H);0.66(m,2H);0.45(m,1H);0.38(m,1H).
実施例番号2-340:1H-NMR(400.0 MHz,DMSO-d6):δ=11.86(br s,1H);7.93(d,1H);7.86(d,1H);7.31(t,1H);5.01(s,2H);4.38(q,2H);3.38(d,2H);1.48(t,3H);1.19(m,1H);0.71(m,2H);0.47(m,2H).
実施例番号2-353:1H-NMR(400.0 MHz,DMSO-d6):δ=11.74(br s,1H);7.82(d,1H);7.56(d,1H);4.36(q,2H);4.07(s,2H);2.17(s,3H);1.47(t,3H).
実施例番号2-354:1H-NMR(400.0 MHz,DMSO-d6):δ=11.78(br s,1H);7.88(d,1H);7.65(d,1H);4.56(d,1H);4.48(d,1H);4.36(q,2H);2.78(s,3H);1.47(t,3H).
実施例番号2-355:1H-NMR(400.0 MHz,DMSO-d6):δ=11.80(br s,1H);7.90(d,1H);7.68(d,1H);4.97(br s,2H);4.36(q,2H);3.19(s,3H);1.47(t,3H).
実施例番号2-356:1H-NMR(400.0 MHz,DMSO-d6):δ=11.76(br s,1H);7.81(d,1H);7.56(d,1H);4.36(q,2H);4.09(s,2H);2.66(q,2H);1.47(t,3H);1.25(t,3H).
実施例番号2-357:1H-NMR(400.0 MHz,DMSO-d6):δ=11.80(br s,1H);7.88(d,1H);7.65(d,1H);4.52(d,1H);4.43(d,1H);4.36(q,2H);3.02(m,1H);2.92(m,1H);1.47(t,3H);1.30(t,3H).
実施例番号2-358:1H-NMR(400.0 MHz,DMSO-d6):δ=11.81(br s,1H);7.90(d,1H);7.68(d,1H);4.92(br s,2H);4.36(q,2H);3.31(q,2H);1.47(t,3H);1.33(t,3H).
実施例番号2-362:1H-NMR(400.0 MHz,DMSO-d6):δ=11.71(br s,1H);8.03(d,1H);7.34(d,1H);4.35(q,2H);4.10(s,2H);2.19(s,3H);1.47(t,3H).
実施例番号2-363:1H-NMR(400.0 MHz,DMSO-d6):δ=11.76(br s,1H);8.09(d,1H);7.42(d,1H);4.59(d,1H);4.52(d,1H);4.35(q,2H);2.79(s,3H);1.47(t,3H).
実施例番号2-364:1H-NMR(400.0 MHz,DMSO-d6):δ=11.78(br s,1H);8.11(d,1H);7.45(d,1H);4.99(br s,2H);4.35(q,2H);3.19(s,3H);1.47(t,3H).
実施例番号2-380:1H-NMR(400.0 MHz,DMSO-d6):δ=11.85(br s,1H);7.93(d,1H);7.79(d,1H);4.40(q,2H);4.04(s,2H);2.23(s,3H);1.49(t,3H).
実施例番号2-381:1H-NMR(400.0 MHz,DMSO-d6):δ=11.94(br s,1H);8.00(d,1H);7.88(d,1H);4.49(d,1H);4.46(d,1H);4.40(q,2H);2.82(s,3H);1.49(t,3H).
実施例番号2-382:1H-NMR(400.0 MHz,DMSO-d6):δ=11.94(br s,1H);7.98(d,1H);7.85(d,1H);5.00(br s,2H);4.35(q,2H);3.25(s,3H);1.46(t,3H).
実施例番号2-383:1H-NMR(400.0 MHz,DMSO-d6):δ=11.86(br s,1H);7.93(d,1H);7.79(d,1H);4.40(q,2H);4.07(s,2H);2.73(q,2H);1.49(t,3H);1.26(t,3H).
実施例番号2-384:1H-NMR(400.0 MHz,DMSO-d6):δ=11.91(br s,1H);8.00(d,1H);7.87(d,1H);4.42(m,4H);3.08(m,1H);2.96(m,1H);1.49(t,3H);1.30(t,3H).
実施例番号2-385:1H-NMR(400.0 MHz,DMSO-d6):δ=11.94(br s,1H);8.01(d,1H);7.93(d,1H);4.96(br s,2H);4.40(q,2H);3.37(q,2H);1.49(t,3H);1.34(t,3H).
実施例番号2-404:1H-NMR(400.0 MHz,DMSO-d6):δ=11.78(br s,1H);7.78(d,1H);7.73(d,1H);7.38(t,1H);4.39(q,2H);4.09(br s,2H);2.16(s,3H);1.48(t,3H).
実施例番号2-405:1H-NMR(400.0 MHz,DMSO-d6):δ=11.82(br s,1H);7.85(d,1H);7.83(d,1H);7.40(t,1H);4.59(d,1H);4.52(d,1H);4.40(q,2H);2.81(s,3H);1.49(t,3H).
実施例番号2-406:1H-NMR(400.0 MHz,DMSO-d6):δ=11.82(br s,1H);7.88(br s,1H);7.36(t,1H);5.10(s,2H);4.40(q,2);3.24(s,3H);1.49(t,3H).
実施例番号2-407:1H-NMR(400.0 MHz,DMSO-d6):δ=11.77(br s,1H);7.78(d,1H);7.72(d,1H);7.36(t,1H);4.39(q,2H);4.12(br s,2H);2.67(q,2H);1.48(t,3H);1.24(t,3H).
実施例番号2-408:1H-NMR(400.0 MHz,DMSO-d6):δ=11.83(br s,1H);7.85(d,1H);7.82(d,1H),7.37(t,1H);4.55(d,1H);4.48(d,1H);4.40(q,2H);3.10(m,1H);2.99(m,1H);1.48(t,3H);1.30(t,3H).
実施例番号2-409:1H-NMR(400.0 MHz,DMSO-d6):δ=11.89(br s,1H);7.87(d,1H);7.84(d,1H);7.33(t,1H);5.04(br s,2H);4.38(q,2H);3.40(q,2H);3.32(s,3H);1.48(t,3H);1.35(t,3H).
実施例番号2-493:1H-NMR(400.0 MHz,DMSO-d6):δ=11.68(br s,1H);7.74(d,1H);7.71(d,1H);4.36(q,2H);4.04(s,2H);2.96(q,2H);2.11(m,1H);1.48(t,3H);1.24(t,3H);0.91(m,2H);0.51(m,2H).
実施例番号2-559:1H-NMR(400.0 MHz,CDCl3):δ=10.34(br s,1H);7.58(d,1H);7.49(d,1H);4.49(q,2H);4.10(s,3H);2.19(s,3H);1.63(t,3H).
実施例番号2-561:1H-NMR(400.0 MHz,CDCl3):δ=10.4(br s,1H);7.68(d,1H);7.58(d,1H);4.88(s,2H);4.48(q,2H);3.05(s,3H);1.61(t,3H).
実施例番号3-37:1H-NMR(400.0 MHz,DMSO-d6):δ=11.65(br s,1H);7.98(d,1H);7.73(d,1H);4.36(s,2H);4.31(t,2H);3.40(s,3H);2.56(s,3H);2.21(s,3H);1.89(m,2H);0.89(t,3H).
実施例番号3-38:1H-NMR(400.0 MHz,DMSO-d6):δ=11.71(br s,1H);8.05(d,1H);7.80(d,1H);4.99(d,1H);4.64(d,1H);3.41(s,3H);2.81(s,3H);2.53(s,3H);1.89(m,2H);0.89(t,3H).
実施例番号3-39:1H-NMR(400.0 MHz,DMSO-d6):δ=11.72(br s,1H);8.11(d,2H);7.85(d,1H);5.41(br s,2H);4.31(t,2H);3.40(s,3H);3.19(s,3H);2.58(s,3H);1.90(m,2H);0.89(t,3H).
実施例番号3-86:1H-NMR(400.0 MHz,CDCl3):δ=10.59(br s,1H);7.67(m,2H);4.42(t,2H);3.94(s,2H);2.67(s,3H);2.66(m,2H);2.03(m,2H);1.31(t,3H);0.99(t,3H).
実施例番号3-88:1H-NMR(400.0 MHz,DMSO-d6):δ=11.70(br s,1H);7.83(d,1H);7.79(d,1H);4.84(br s,2H);4.31(t,2H);3.33(m,3H);2.58(s,3H);1.90(m,2H);1.33(t,3H);0.89(t,3H).
実施例番号3-107:1H-NMR(400.0 MHz,DMSO-d6):δ=11.53(br s,1H);7.64(d,1H);7.61(d,1H);7.36(t,1H);4.32(t,2H);3.98(s,2H);2.50(s,3H);2.16(s,3H);1.91(m,2H);0.90(t,3H).
実施例番号3-108:1H-NMR(400.0 MHz,DMSO-d6):δ=11.57(br s,1H);7.69(d,1H);7.65(d,1H);7.38(t,1H);4.45(d,1H);4.36(d,1H);4.31(t,2H);2.81(s,3H);2.46(s,3H);1.89(m,2H);0.89(t,3H).
実施例番号3-109:1H-NMR(400.0 MHz,DMSO-d6):δ=11.59(br s,1H);7.75(d,1H);7.69(d,1H);7.33(t,1H);4.94(s,2H);4.30(t,3H);3.25(s,3H);2.52(s,3H);1.89(m,2H);0.89(t,3H).
実施例番号3-134:1H-NMR(400.0 MHz,CDCl3):δ=9.94(br s,1H);8.07(d,1H);7.64(d,1H);4.37(t,2H);4.12(s,3H);3.96(s,2H);2.25(s,3H);2.02(m,2H);0.98(t,3H).
実施例番号3-135:1H-NMR(400.0 MHz,CDCl3):δ=10.01(br s,1H);8.10(d,1H);7.70(d,1H);4.44(d,1H);4.36(t,2H);4.18(d,1H);4.07(s,3H);2.76(s,3H);2.02(m,2H);0.98(t,3H).
実施例番号3-136:1H-NMR(400.0 MHz,CDCl3):δ=9.82(br s,1H);8.14(d,1H);7.71(d,1H);4.72(s,2H);4.35(t,2H);4.08(s,3H);3.07(s,3H);2.02(m,2H);0.98(t,3H).
実施例番号3-161:1H-NMR(400.0 MHz,DMSO-d6):δ=11.67(br s,1H);7.91(d,1H);7.72(d,1H);4.38(t,2H);4.19(s,2H);2.46(s,3H);2.22(s,3H);1.92(m,2H);0.91(t,3H).
実施例番号3-162:1H-NMR(400.0 MHz,DMSO-d6):δ=11.72(br s,1H);8.00(d,1H);7.82(d,1H);4.64(d,1H);4.59(d,1H);4.38(t,2H);2.80(s,3H);2.40(s,3H);1.92(m,2H);0.91(t,3H).
実施例番号3-163:1H-NMR(400.0 MHz,DMSO-d6):δ=11.75(br s,1H);8.02(d,1H);7.87(d,1H);5.15(br s,2H);4.38(t,2H);3.23(t,3H);2.39(s,3H);1.92(m,2H);0.91(t,3H).
実施例番号3-170:1H-NMR(400.0 MHz,DMSO-d6):δ=11.59(br s,1H);7.79(d,1H);7.67(d,1H);7.39(t,1H);4.38(t,2H);2.43(s,3H);2.17(s,3H);1.91(m,2H);0.90(t,3H).
実施例番号3-171:1H-NMR(400.0 MHz,DMSO-d6):δ=11.64(br s,1H);7.86(d,1H);7.76(d,1H);7.41(t,1H);4.72(d,1H);4.66(d,1H);2.80(s,3H);2.38(s,3H);1.92(m,2H);0.90(t,3H).
実施例番号3-172:1H-NMR(400.0 MHz,DMSO-d6):δ=11.66(br s,1H);7.90(d,1H);7.82(d,1H);7.38(t,1H);5.25(br s,2H);4.38(t,2H);3.22(s,3H);2.38(s,3H);1.92(m,2H);0.91(t,3H).
実施例番号3-199:1H-NMR(400.0 MHz,DMSO-d6):δ=11.94(br s,1H);8.38(d,1H);8.11(d,1H);6.19(d,1H);4.88(d,1H);4.36(t,2H);3.65(s,3H);3.27(s,3H);1.90(m,2H);0.91(t,3H).
実施例番号3-287:1H-NMR(400.0 MHz,DMSO-d6):δ=11.57(br s,1H);7.48(d,1H);7.34(d,1H);4.30(t,2H);3.96(s,2H);2.48(s,3H);2.13(s,3H);1.88(m,2H);0.88(t,3H).
実施例番号3-289:1H-NMR(400.0 MHz,DMSO-d6):δ=11.64(br s,1H);7.59(d,1H);7.41(d,1H);4.86(s,2H);4.31(t,2H);3.15(s,3H);2.54(s,3H);1.89(m,2H);0.88(t,3H).
実施例番号3-296:1H-NMR(400.0 MHz,CDCl3):δ=10.00(br s,1H);7.74(d,1H);7.67(d,1H);4.43(t,2H);4.05(s,3H);2.23(s,3H);2.04(m,2H);1.00(t,3H).
実施例番号3-297:1H-NMR(400.0 MHz,DMSO-d6):δ=11.90(br s,1H);7.97(d,1H);7.92(d,1H);4.48(d,1H);4.43(d,1H);4.33(t,2H);2.82(s,3H);1.90(m,2H);0.89(t,3H).
実施例番号3-298:1H-NMR(400.0 MHz,DMSO-d6):δ=11.92(br s,1H);8.00(m,2H);4.98(br s,2H);4.33(t,2H);3.25(s,3H);1.90(m,2H);0.89(t,3H).
実施例番号3-299:1H-NMR(400.0 MHz,DMSO-d6):δ=11.86(br s,1H);7.90(d,1H);7.84(d,1H);4.33(t,2H);4.05(s,3H);2.72(q,2H);1.90(m,2H);1.25(t,3H);0.89(t,3H).
実施例番号3-301:1H-NMR(400.0 MHz,CDCl3):δ=10.60(br s,1H);7.80(d,1H);7.77(d,1H);4.83(s,2H);4.38(t,2H);3.19(q,2H);2.02(m,2H);1.47(t,3H);0.98(t,3H).
実施例番号3-308:1H-NMR(400.0 MHz,DMSO-d6):δ=11.85(br s,1H);87.90(d,1H);7.84(d,1H);5.88(m,1H);5.26(d,1H);5.17(d,1H);4.33(t,2H);3.96(s,2H);3.38(d,2H);1.90(m,2H);0.89(t,3H).
実施例番号3-311:1H-NMR(400.0 MHz,DMSO-d6):δ=11.87(br s,1H);7.93(d,1H);7.89(d,1H);4.33(t,2H);4.26(s,2H);3.76(q,2H);1.90(m,2H);0.89(t,3H).
実施例番号3-314:1H-NMR(400.0 MHz,DMSO-d6):δ=11.85(br s,1H);7.90(d,1H);7.83(d,1H);4.33(t,2H);4.10(s,2H);2.68(d,2H);1.90(m,2H);1.02(m,1H);0.89(t,3H);0.55(m,2H);0.25(m,2H).
実施例番号3-320:1H-NMR(400.0 MHz,DMSO-d6):δ=11.78(br s,1H);7.76(m,2H);7.38(t,1H);4.32(t,2H);4.07(s,2H);2.15(s,3H);1.89(m,2H);0.89(t,3H).
実施例番号3-322:1H-NMR(400.0 MHz,DMSO-d6):δ=11.83(br s,1H);7.92(d,1H);7.86(d,1H);7.35(t,1H);5.07(s,2H);4.33(t,2H);3.24(s,3H);1.89(m,2H);0.89(t,3H).
実施例番号3-323:1H-NMR(400.0 MHz,DMSO-d6):δ=11.77(br s,1H);7.75(m,2H);7.36(t,1H);4.32(t,2H);4.09(s,2H);2.65(q,2H);1.89(m,2H);1.23(t,3H);0.89(t,3H).
実施例番号3-324:1H-NMR(400.0 MHz,DMSO-d6):δ=10.88(br s,1H);7.64(s,2H);7.16(t,1H);4.39(t,2H);4.32(s,3H);2.95(m,2H);2.00(m,2H);1.39(t,3H);0.98(t,3H).
実施例番号3-325:1H-NMR(400.0 MHz,DMSO-d6):δ=11.95(br s,1H);7.86(d,1H);7.82(d,1H);7.37(t,1H);4.49(s,2H);4.33(t,2H);3.09(m,1H);2.98(m,1H);1.88(m,2H);1.29(t,3H);0.89(t,3H).
実施例番号3-362:1H-NMR(400.0 MHz,DMSO-d6):δ=11.70(br s,1H);8.03(d,1H);7.33(d,1H);4.30(t,2H);4.10(s,2H);2.19(s,3H);1.88(m,2H);0.88(t,3H).
実施例番号3-363:1H-NMR(400.0 MHz,DMSO-d6):11.74(br s,1H);8.09(d,1H);7.41(d,1H);4.59(d,1H);4.52(d,1H);4.30(t,2H);2.79(s,3H);1.88(m,2H);0.88(t,3H).
実施例番号3-380:1H-NMR(400.0 MHz,DMSO-d6):δ=11.83(br s,1H);7.93(d,1H);7.78(d,1H);4.35(t,2H);4.04(s,2H);2.23(s,3H);1.91(m,2H);0.90(t,3H).
実施例番号3-381:1H-NMR(400.0 MHz,DMSO-d6):δ=11.94(br s,1H);8.00(d,1H);7.86(d,1H);4.50(d,1H);4.45(d,1H);4.35(t,2H);2.82(s,3H);1.89(m,2H);0.89(t,3H).
実施例番号3-382:1H-NMR(400.0 MHz,DMSO-d6):δ=11.91(br s,1H);8.01(d,1H);7.88(d,1H);5.00(br s,2H);4.33(t,3H);3.26(s,3H);1.90(m,2H);0.89(t,3H).
実施例番号3-383:1H-NMR(400.0 MHz,DMSO-d6):δ=11.84(br s,1H);7.93(d,1H);7.77(d,1H);4.35(t,2H);4.07(s,2H);2.73(q,2H);1.91(m,2H);1.26(t,3H);0.89(t,3H).
実施例番号3-384:1H-NMR(400.0 MHz,DMSO-d6):δ=11.89(br s,1H);8.00(d,1H);7.86(d,1H);4.47(d,1H);4.40(d,1H);4.35(t,2H);3.09(m,1H);2.98(m,1H);1.91(m,2H;1.30(t,3H);0.89(t,3H).
実施例番号3-3851H-NMR(400.0 MHz,DMSO-d6):δ=11.98(br s,1H);7.97(d,1H);7.83(d,1H);4.94(br s,2H);4.29(t,2H);3.37(q,2H);1.91(s,3H);1.87(q,2H);1.34(t,3H);0.89(t,3H).
a)10重量部の式(I)の化合物および/またはその塩と90重量部の不活性物質としてのタルクを混合し、混合物をハンマーミルで粉砕することによって粉剤製品を得る。
10重量部のリグノスルホン酸カルシウム、
5重量部のラウリル硫酸ナトリウム、
3重量部のポリビニルアルコールならびに
7重量部のカオリン
を混合し、混合物をピン止めディスクミルで粉砕し、粉末を流動床中で造粒液として水を噴霧塗布することによって造粒することによって、顆粒水和剤を得る。
5重量部の2,2’-ジナフチルメタン-6,6’-ジスルホン酸ナトリウム、
2重量部のオレオイルメチルタウリン酸ナトリウム、
1重量部のポリビニルアルコール、
17重量部の炭酸カルシウムならびに
50重量部の水
をコロイドミルで均質化および予備粉砕し、次いで、混合物をヘッドミルで粉砕し、得られた懸濁液を一相ノズルを用いて噴霧塔で霧化および乾燥することによっても、顆粒水和剤を得る。
1.有害植物に対する出芽前除草作用
単子葉および双子葉雑草植物ならびに作物植物の種子を、木質繊維ポットの砂壌土中に並べ、土で覆う。次いで、水和剤(WP)の形態にまたは乳剤(EC)として製剤化された本発明の化合物を、0.2%の湿潤剤を添加して、600~800l/haと同等の水施用量で水性懸濁液または乳濁液の形態で、覆っている土の表面に施用する。処理後、ポットを温室に入れ、試験植物のための良好な成長条件下に保つ。試験植物の損傷を、未処理の対照と比較して、3週間の試験期間後に視覚的に評価する(パーセントでの除草活性(%):100%活性=植物が死滅した、0%活性=対照植物と同様)。本発明の多数の化合物は、多数の重要な有害植物に対して非常に良好な作用を示した。以下の表は、代表的な様式で、本発明による化合物の出芽後除草作用を示し、除草活性は%で言及される。
ABUTH イチビ(Abutilon theophrasti) ALOMY ノスズメノテッポウ(Alopecurus myosuroides)
AVEFA カラスムギ(Avena fatua) AMARE アオゲイトウ(Amaranthus retroflexus)
CYPES ショクヨウガヤツリ(Cyperus esculentus) DIGSA オニメヒシバ(Digitaria sanguinalis)
ECHCG イヌビエ(Echinocloa crusgalli) HORMU ムギクサ(Hordeum murinum)
LOLMU イタリアンライグラス(Lolium multiflorum) LOLRI ボウムギ(Lolium rigidum)
MATIN イヌカミツレ(Matricaria inodora) PHBPU マルバアサガオ(Pharbitis purpurea)
POLCO ポリゴナム・コンボルブルス(Polygonum convolvulus) SETVI エノコログサ(Setaria viridis)
STEME コハコベ(Stellaria media) VERPE オオイヌノフグリ(Veronica persica)
VIOTR サンシキスミレ(Viola tricolor)
単子葉および双子葉雑草ならびに作物植物の種子を、木質繊維ポットの砂壌土壌中に並べ、土で覆い、良好な成長条件下温室で栽培する。播種の2~3週間後、試験植物を一葉段階で処理する。次いで、水和剤(WP)の形態にまたは乳剤(EC)として製剤化された本発明の化合物を、0.2%の湿潤剤を添加して、600~800l/haと同等の水施用量で水性懸濁液または乳濁液の形態で、植物の緑色部分に噴霧する。試験植物を最適成長条件下で温室内に約3週間放置した後、調製物の作用を未処理対照と比較して視覚的に評価する(パーセントでの除草作用(%):100%活性=植物が死滅した、0%活性=対照植物と同様)。本発明の多数の化合物は、多数の重要な有害植物に対して非常に良好な作用を示した。以下の表は、代表的な様式で、本発明による化合物の出芽後除草作用を示し、除草活性は%で言及される。
以下の実験では、多数の本発明の化合物ならびにD1(国際公開第2012/028579号パンフレット)およびD2(国際公開第2018/202535号パンフレット)から構造的に最も近い既知の化合物の除草作用を、出芽前法および出芽後法によって上記の条件下で比較した。表に示される例番号は、それぞれの文献に開示される化合物に関する。D1およびD2に開示される化合物に加えて、D1またはD2に包含されるが、そこに明記されている化合物ではない以下の化合物V-1~V-14を比較実験に使用した:
V-1:2-(メチルスルファニル)-3-(メチルスルフィニル)-N-(1-メチル-1H-テトラゾール-5-イル)-4-(トリフルオロメチル)ベンズアミド
V-2:2-(メチルスルファニル)-3-(メチルスルホニル)-N-(1-メチル-1H-テトラゾール-5-イル)-4-(トリフルオロメチル)ベンズアミド
V-3:2,3-ビス(エチルスルファニル)-N-(1-メチル-1H-テトラゾール-5-イル)-4-(トリフルオロメチル)ベンズアミド
V-4:2-クロロ-3-(エチルスルファニル)-N-(1-メチル-1H-テトラゾール-5-イル)-4-(トリフルオロメチル)ベンズアミド
V-5:2-クロロ-4-ヨード-3-(メチルスルファニル)-N-(1-メチル-1H-テトラゾール-5-イル)ベンズアミド
V-6:2-クロロ-4-ヨード-3-(メチルスルフィニル)-N-(1-メチル-1H-テトラゾール-5-イル)ベンズアミド
V-7:2-クロロ-4-ヨード-3-(メチルスルホニル)-N-(1-メチル-1H-テトラゾール-5-イル)ベンズアミド
V-8:2-ブロモ-3-(メチルスルファニル)-N-(1-メチル-1H-テトラゾール-5-イル)-4-(トリフルオロメチル)ベンズアミド
V-9:2-ブロモ-3-(メチルスルフィニル)-N-(1-メチル-1H-テトラゾール-5-イル)-4-(トリフルオロメチル)ベンズアミド
V-10:2-ブロモ-3-(メチルスルホニル)-N-(1-メチル-1H-テトラゾール-5-イル)-4-(トリフルオロメチル)ベンズアミド
V-11:2-ブロモ-3-(エチルスルファニル)-N-(1-メチル-1H-テトラゾール-5-イル)-4-(トリフルオロメチル)ベンズアミド
V-12:2-ブロモ-3-(エチルスルフィニル)-N-(1-メチル-1H-テトラゾール-5-イル)-4-(トリフルオロメチル)ベンズアミド
V-13:2-ブロモ-3-(エチルスルホニル)-N-(1-メチル-1H-テトラゾール-5-イル)-4-(トリフルオロメチル)ベンズアミド
V-14:2-シクロプロピル-3-(エチルスルファニル)-N-(1-メチル-1H-テトラゾール-5-イル)-4-(トリフルオロメチル)ベンズアミド
Claims (12)
- 式(I)のアリールカルボキサミドまたはその塩
RXは、(C1~C6)-アルキルまたは(C1~C6)-アルキル-O-(C1~C6)-アルキルであり、
Xは、ハロゲン、(C1~C6)-アルキル、ハロ-(C1~C6)-アルキル、(C3~C6)-シクロアルキル、R1O、R2(O)nSまたはR1O-(C1~C6)-アルキルであり、
Yは、ハロゲン、(C1~C6)-アルキル、ハロ-(C1~C6)-アルキル、R1OまたはR2(O)nSであり、
Zは、(C1~C6)-アルキル、(C3~C6)-シクロアルキル、(C3~C6)-シクロアルキル-(C1~C6)-アルキル、(C1~C6)-アルキル-O-(C1~C6)-アルキル、(C1~C6)-ハロアルキル、(C2~C6)-アルケニルまたは(C2~C6)-アルキニルであり、
R1は、(C1~C6)-アルキルまたはハロ-(C1~C6)-アルキルであり、
R2は、(C1~C6)-アルキルであり、
nは、0、1または2である)。 - RXが、(C1~C3)-アルキルまたは(C1~C3)-アルキル-O-(C1~C3)-アルキルであり、
Xが、ハロゲン、(C1~C3)-アルキル、ハロ-(C1~C3)-アルキル、(C3~C6)-シクロアルキル、R1O、R2(O)nSまたはR1O-(C1~C3)-アルキルであり、
Yが、ハロゲン、(C1~C4)-アルキル、ハロ-(C1~C4)-アルキル、R1OまたはR2(O)nSであり、
Zが、(C1~C4)-アルキル、(C3~C6)-シクロアルキル、(C3~C6)-シクロアルキル-(C1~C3)-アルキル、(C1~C3)-アルキル-O-(C1~C3)-アルキル、(C1~C3)-ハロアルキル、(C2~C6)-アルケニルまたは(C2~C6)-アルキニルであり、
R1が、(C1~C3)-アルキルまたはハロ-(C1~C3)-アルキルであり、
R2が、(C1~C3)-アルキルであり、
nが、0、1または2である、
請求項1に記載のアリールカルボキサミド。 - RXが、Me、EtまたはPrであり、
Xが、F、Cl、Br、I、Me、Et、c-Pr、CF3、C2F5、CH2OMe、OMe、SMe、SO2Me、SEtまたはSO2Etであり、
Yが、Cl、Br、I、Me、CF3、CHF2、C2F5、SMeまたはSO2Meであり、
Zが、Me、Et、i-Pr、c-Pr、CH2-c-Pr、(CH2)2OMe、アリルまたはCH2CF3であり、
nが、0、1または2である、
請求項1または2に記載のアリールカルボキサミド。 - 1種または複数の請求項1から3のいずれか一項に記載の一般式(I)の化合物またはその塩を含むことを特徴とする、除草性組成物または植物成長調節組成物。
- 製剤補助剤をさらに含む、請求項4に記載の除草性組成物。
- 少なくとも1種の殺虫剤、殺ダニ剤、除草剤、殺真菌剤、薬害軽減剤および/または成長調節剤の群のさらなる有効成分を含む、請求項4または5に記載の除草性組成物。
- 薬害軽減剤を含む、請求項4または5に記載の除草性組成物。
- 前記薬害軽減剤が、メフェンピル-ジエチル、シプロスルファミド、イソキサジフェン-エチル、クロキントセット-メキシル、ベノキサコールおよびジクロルミドからなる群から選択される、請求項7に記載の除草性組成物。
- 有効量の少なくとも1種の請求項1から3のいずれか一項に記載の式(I)の化合物または請求項4から8のいずれか一項に記載の除草性組成物を植物または不要な植生の部位に施用することを特徴とする、不要な植物を防除する方法。
- 不要な植物を防除するための、請求項1から3のいずれか一項に記載の式(I)の化合物または請求項4から8のいずれか一項に記載の除草性組成物の使用。
- 前記式(I)の化合物が有用植物の作物において不要な植物を防除するために使用されることを特徴とする、請求項10に記載の使用。
- 前記有用植物がトランスジェニック有用植物であることを特徴とする、請求項11に記載の使用。
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PCT/EP2020/050498 WO2020148175A1 (de) | 2019-01-14 | 2020-01-10 | Herbizide substituierte n-tetrazolylarylcarboxamide |
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UA128004C2 (uk) | 2024-03-06 |
JP2022518414A (ja) | 2022-03-15 |
WO2020148175A1 (de) | 2020-07-23 |
AR117812A1 (es) | 2021-08-25 |
PL3911633T3 (pl) | 2023-02-27 |
EP3911633B1 (de) | 2022-11-23 |
EA202191910A1 (ru) | 2021-11-16 |
EP3911633A1 (de) | 2021-11-24 |
BR112021010264A2 (pt) | 2021-08-17 |
US20220119358A1 (en) | 2022-04-21 |
MX2021008433A (es) | 2021-08-19 |
CN113544124A (zh) | 2021-10-22 |
ES2935535T3 (es) | 2023-03-07 |
CA3126321A1 (en) | 2020-07-23 |
CN113544124B (zh) | 2024-05-28 |
AU2020209871A1 (en) | 2021-08-05 |
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