JP7394079B2 - 置換2-ヘテロアリールオキシピリジン類及びその塩並びにそれらの除草剤としての使用 - Google Patents
置換2-ヘテロアリールオキシピリジン類及びその塩並びにそれらの除草剤としての使用 Download PDFInfo
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- JP7394079B2 JP7394079B2 JP2020571748A JP2020571748A JP7394079B2 JP 7394079 B2 JP7394079 B2 JP 7394079B2 JP 2020571748 A JP2020571748 A JP 2020571748A JP 2020571748 A JP2020571748 A JP 2020571748A JP 7394079 B2 JP7394079 B2 JP 7394079B2
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- 150000003839 salts Chemical class 0.000 title claims description 55
- 239000004009 herbicide Substances 0.000 title claims description 44
- -1 cyano, methyl Chemical group 0.000 claims description 325
- 150000001875 compounds Chemical class 0.000 claims description 162
- 239000000203 mixture Substances 0.000 claims description 71
- 239000001257 hydrogen Substances 0.000 claims description 43
- 229910052739 hydrogen Inorganic materials 0.000 claims description 43
- 238000000034 method Methods 0.000 claims description 36
- 230000002363 herbicidal effect Effects 0.000 claims description 35
- 244000038559 crop plants Species 0.000 claims description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
- 238000009472 formulation Methods 0.000 claims description 22
- 150000002431 hydrogen Chemical group 0.000 claims description 20
- 230000009261 transgenic effect Effects 0.000 claims description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 239000000460 chlorine Substances 0.000 claims description 15
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- 239000011737 fluorine Substances 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical group [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 239000013543 active substance Substances 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 231100000674 Phytotoxicity Toxicity 0.000 claims description 5
- 239000003905 agrochemical Substances 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- OAWUUPVZMNKZRY-UHFFFAOYSA-N cyprosulfamide Chemical compound COC1=CC=CC=C1C(=O)NS(=O)(=O)C1=CC=C(C(=O)NC2CC2)C=C1 OAWUUPVZMNKZRY-UHFFFAOYSA-N 0.000 claims description 4
- OPGCOAPTHCZZIW-UHFFFAOYSA-N diethyl 1-(2,4-dichlorophenyl)-5-methyl-4h-pyrazole-3,5-dicarboxylate Chemical group CCOC(=O)C1(C)CC(C(=O)OCC)=NN1C1=CC=C(Cl)C=C1Cl OPGCOAPTHCZZIW-UHFFFAOYSA-N 0.000 claims description 4
- MWKVXOJATACCCH-UHFFFAOYSA-N isoxadifen-ethyl Chemical group C1C(C(=O)OCC)=NOC1(C=1C=CC=CC=1)C1=CC=CC=C1 MWKVXOJATACCCH-UHFFFAOYSA-N 0.000 claims description 4
- 239000011593 sulfur Chemical group 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 230000000895 acaricidal effect Effects 0.000 claims description 3
- 239000000642 acaricide Substances 0.000 claims description 3
- 239000002671 adjuvant Substances 0.000 claims description 3
- 239000003638 chemical reducing agent Substances 0.000 claims description 3
- 239000000417 fungicide Substances 0.000 claims description 3
- 239000003630 growth substance Substances 0.000 claims description 3
- 239000002917 insecticide Substances 0.000 claims description 3
- COYBRKAVBMYYSF-UHFFFAOYSA-N heptan-2-yl [(5-chloroquinolin-8-yl)oxy]acetate Chemical group C1=CN=C2C(OCC(=O)OC(C)CCCCC)=CC=C(Cl)C2=C1 COYBRKAVBMYYSF-UHFFFAOYSA-N 0.000 claims description 2
- 244000045561 useful plants Species 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 description 112
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 97
- 229910052736 halogen Inorganic materials 0.000 description 35
- 150000002367 halogens Chemical class 0.000 description 35
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- 230000000694 effects Effects 0.000 description 30
- 125000000623 heterocyclic group Chemical group 0.000 description 28
- 125000000217 alkyl group Chemical group 0.000 description 23
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 22
- 125000004432 carbon atom Chemical group C* 0.000 description 22
- 125000004093 cyano group Chemical group *C#N 0.000 description 22
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 20
- 239000002585 base Substances 0.000 description 19
- 150000003222 pyridines Chemical class 0.000 description 18
- 239000002904 solvent Substances 0.000 description 17
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 239000008187 granular material Substances 0.000 description 15
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 14
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 14
- 241000209094 Oryza Species 0.000 description 14
- 230000008635 plant growth Effects 0.000 description 14
- 239000011734 sodium Substances 0.000 description 14
- 229910052708 sodium Inorganic materials 0.000 description 14
- 239000002689 soil Substances 0.000 description 14
- 239000000126 substance Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 235000007164 Oryza sativa Nutrition 0.000 description 13
- 230000001276 controlling effect Effects 0.000 description 13
- 239000000839 emulsion Substances 0.000 description 13
- 239000003960 organic solvent Substances 0.000 description 13
- 238000002360 preparation method Methods 0.000 description 13
- 235000009566 rice Nutrition 0.000 description 13
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 description 12
- 238000005481 NMR spectroscopy Methods 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 12
- 230000012010 growth Effects 0.000 description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 11
- 244000292693 Poa annua Species 0.000 description 11
- 240000006694 Stellaria media Species 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 11
- 229910052700 potassium Inorganic materials 0.000 description 11
- 239000011591 potassium Substances 0.000 description 11
- 239000000843 powder Substances 0.000 description 11
- 230000001105 regulatory effect Effects 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 240000003461 Setaria viridis Species 0.000 description 10
- 235000002248 Setaria viridis Nutrition 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 9
- 244000062793 Sorghum vulgare Species 0.000 description 9
- 125000003342 alkenyl group Chemical group 0.000 description 9
- 238000009835 boiling Methods 0.000 description 9
- 125000001072 heteroaryl group Chemical group 0.000 description 9
- 108090000623 proteins and genes Proteins 0.000 description 9
- 238000000746 purification Methods 0.000 description 9
- 240000006995 Abutilon theophrasti Species 0.000 description 8
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 8
- 244000058871 Echinochloa crus-galli Species 0.000 description 8
- 241000209219 Hordeum Species 0.000 description 8
- 235000011999 Panicum crusgalli Nutrition 0.000 description 8
- 241000404538 Tripleurospermum maritimum subsp. inodorum Species 0.000 description 8
- 240000008042 Zea mays Species 0.000 description 8
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 8
- 125000000304 alkynyl group Chemical group 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 8
- 235000013339 cereals Nutrition 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 125000005842 heteroatom Chemical group 0.000 description 8
- 239000000575 pesticide Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 7
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 7
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 7
- 244000237956 Amaranthus retroflexus Species 0.000 description 7
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 description 7
- 235000007340 Hordeum vulgare Nutrition 0.000 description 7
- 241000033016 Lolium rigidum Species 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 125000003636 chemical group Chemical group 0.000 description 7
- 238000004440 column chromatography Methods 0.000 description 7
- 230000000875 corresponding effect Effects 0.000 description 7
- 125000004430 oxygen atom Chemical group O* 0.000 description 7
- 239000005648 plant growth regulator Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 7
- 238000011282 treatment Methods 0.000 description 7
- 125000006648 (C1-C8) haloalkyl group Chemical group 0.000 description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 6
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 6
- 241000209056 Secale Species 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 241000209140 Triticum Species 0.000 description 6
- 235000021307 Triticum Nutrition 0.000 description 6
- 229910052783 alkali metal Inorganic materials 0.000 description 6
- 150000001340 alkali metals Chemical class 0.000 description 6
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- 235000014113 dietary fatty acids Nutrition 0.000 description 6
- 239000003995 emulsifying agent Substances 0.000 description 6
- 229930195729 fatty acid Natural products 0.000 description 6
- 239000000194 fatty acid Substances 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 235000019713 millet Nutrition 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 5
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 description 5
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 description 5
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 5
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 description 5
- 125000006636 (C3-C8) cycloalkylcarbonyl group Chemical group 0.000 description 5
- 244000075850 Avena orientalis Species 0.000 description 5
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 description 5
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 5
- 241000209510 Liliopsida Species 0.000 description 5
- 235000007238 Secale cereale Nutrition 0.000 description 5
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 5
- 235000011054 acetic acid Nutrition 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 210000004027 cell Anatomy 0.000 description 5
- 229910052802 copper Inorganic materials 0.000 description 5
- 239000010949 copper Substances 0.000 description 5
- 230000014509 gene expression Effects 0.000 description 5
- 125000001188 haloalkyl group Chemical group 0.000 description 5
- 235000009973 maize Nutrition 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- 239000004562 water dispersible granule Substances 0.000 description 5
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 description 4
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 description 4
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 description 4
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 description 4
- 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- 108010000700 Acetolactate synthase Proteins 0.000 description 4
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 4
- 108091026890 Coding region Proteins 0.000 description 4
- 235000010469 Glycine max Nutrition 0.000 description 4
- 244000068988 Glycine max Species 0.000 description 4
- 241000219146 Gossypium Species 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 229920002472 Starch Polymers 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 125000001118 alkylidene group Chemical group 0.000 description 4
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 230000008878 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 description 4
- WCGGWVOVFQNRRS-UHFFFAOYSA-N dichloroacetamide Chemical compound NC(=O)C(Cl)Cl WCGGWVOVFQNRRS-UHFFFAOYSA-N 0.000 description 4
- BWUPSGJXXPATLU-UHFFFAOYSA-N dimepiperate Chemical compound C=1C=CC=CC=1C(C)(C)SC(=O)N1CCCCC1 BWUPSGJXXPATLU-UHFFFAOYSA-N 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 241001233957 eudicotyledons Species 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- 239000003337 fertilizer Substances 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 239000008107 starch Substances 0.000 description 4
- 235000019698 starch Nutrition 0.000 description 4
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 4
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 description 3
- 125000004750 (C1-C6) alkylaminosulfonyl group Chemical group 0.000 description 3
- 125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 description 3
- 125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 description 3
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 description 3
- 125000006644 (C2-C6) haloalkynyl group Chemical group 0.000 description 3
- MHULQDZDXMHODA-UHFFFAOYSA-N 1-(2,2-dichloroacetyl)-3,3,8a-trimethyl-2,4,7,8-tetrahydropyrrolo[1,2-a]pyrimidin-6-one Chemical compound C1C(C)(C)CN(C(=O)C(Cl)Cl)C2(C)N1C(=O)CC2 MHULQDZDXMHODA-UHFFFAOYSA-N 0.000 description 3
- YIVXMZJTEQBPQO-UHFFFAOYSA-N 2,4-DB Chemical compound OC(=O)CCCOC1=CC=C(Cl)C=C1Cl YIVXMZJTEQBPQO-UHFFFAOYSA-N 0.000 description 3
- 239000002794 2,4-DB Substances 0.000 description 3
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 3
- XKKUTOFJRZKJPW-UHFFFAOYSA-N 2-(3-bromo-4,6-dimethylpyridin-2-yl)oxy-5-fluoropyrimidine Chemical compound BrC=1C(=NC(=CC=1C)C)OC1=NC=C(C=N1)F XKKUTOFJRZKJPW-UHFFFAOYSA-N 0.000 description 3
- MYBPCMCMKCZTAP-UHFFFAOYSA-N 2-(3-bromo-4-methylpyridin-2-yl)oxypyrimidine Chemical compound BrC=1C(=NC=CC=1C)OC1=NC=CC=N1 MYBPCMCMKCZTAP-UHFFFAOYSA-N 0.000 description 3
- WVQBLGZPHOPPFO-UHFFFAOYSA-N 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(1-methoxypropan-2-yl)acetamide Chemical compound CCC1=CC=CC(C)=C1N(C(C)COC)C(=O)CCl WVQBLGZPHOPPFO-UHFFFAOYSA-N 0.000 description 3
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- 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
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 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
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 150000003457 sulfones 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
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- XQTLDIFVVHJORV-UHFFFAOYSA-N tecnazene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=CC(Cl)=C1Cl XQTLDIFVVHJORV-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
- 239000002562 thickening agent Substances 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 compound COC(=O)C1=CSC(C)=C1S(=O)(=O)NC(=O)N1C(=O)N(C)C(OC)=N1 XSKZXGDFSCCXQX-UHFFFAOYSA-N 0.000 description 1
- 125000003777 thiepinyl 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
- 125000001730 thiiranyl group Chemical group 0.000 description 1
- 125000000464 thioxo group Chemical group S=* 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
- 231100000583 toxicological profile Toxicity 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
- 238000013518 transcription Methods 0.000 description 1
- 230000035897 transcription Effects 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 125000004665 trialkylsilyl 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
- 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
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 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
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 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
- 229960004418 trolamine Drugs 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
- 239000001993 wax Substances 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- UGOMMVLRQDMAQQ-UHFFFAOYSA-N xphos Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 UGOMMVLRQDMAQQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Cultivation Of Plants (AREA)
- Catching Or Destruction (AREA)
Description
Xは、窒素、-CF-又は-CH-を表し、
Aは、酸素、-S(O)n-、-C(R4)(R5)-、-C(=O)-又は-NR6-を表し、
n=0、1又は2であり、
R1は、置換されていても良いアリール、ヘテロアリール、複素環、(C3-C10)-シクロアルキル又は(C3-C10)-シクロアルケニルを表し、ここで、各環若しくは各環系は、基R7から独立に選択される最大5個の置換基によって置換されていても良く;
R2は、他のものとは独立に、ハロゲン、シアノ、ニトロ、ホルミル、ホルムアミド、(C1-C8)-アルキル、(C1-C8)-ハロアルキル、(C2-C8)-アルケニル、(C2-C8)-アルキニル、(C2-C8)-ハロアルケニル、(C2-C8)-ハロアルキニル、(C1-C4)-アルコキシ-(C1-C4)-アルキル、(C1-C4)-ハロアルコキシ-(C1-C4)-アルキル、(C1-C4)-アルキルチオ-(C1-C4)-アルキル、(C1-C4)-アルキルスルフィニル-(C1-C4)-アルキル、(C1-C4)-アルキルスルホニル-(C1-C4)-アルキル、(C1-C8)-アルキルカルボニル、(C1-C8)-ハロアルキルカルボニル、(C3-C8)-シクロアルキルカルボニル、カルボキシル、(C1-C8)-アルコキシカルボニル、(C1-C8)-ハロアルコキシカルボニル、(C3-C8)-シクロアルコキシカルボニル、カルバモイル、(C2-C8)-アルキルアミノカルボニル、(C2-C10)-ジアルキルアミノカルボニル、(C3-C10)-シクロアルキルアミノカルボニル、(C1-C4)-アルコキシカルボニル-(C1-C4)-アルキル、(C1-C4)-ハロアルコキシカルボニル-(C1-C4)-アルキル、カルボキシ-(C1-C4)-アルキル、ヒドロキシ、アミノ、(C1-C8)-アルコキシ、(C1-C8)-ハロアルコキシ、(C1-C8)-アルキルチオ、(C1-C8)-ハロアルキルチオ、(C3-C8)-シクロアルキルチオ、(C1-C8)-アルキルスルフィニル、(C1-C8)-ハロアルキルスルフィニル、(C3-C8)-シクロアルキルスルフィニル、(C1-C8)-アルキルスルホニル、(C1-C8)-ハロアルキルスルホニル、(C3-C8)-シクロアルキルスルホニル、(C1-C8)-アルキルアミノスルホニル、(C2-C8)-ジアルキルアミノスルホニル又は(C3-C8)-トリアルキルシリルを表し、
mは、0、1、2又は3を表し、
R3は、水素、ハロゲン、シアノ、ニトロ、ホルミル、(C1-C8)-アルキル、(C1-C8)-ハロアルキル、(C2-C8)-アルケニル、(C2-C8)-アルキニル、(C2-C8)-ハロアルケニル、(C2-C8)-ハロアルキニル、(C1-C4)-アルコキシ-(C1-C4)-アルキル、(C1-C4)-ハロアルコキシ-(C1-C4)-アルキル、(C1-C4)-アルキルチオ-(C1-C4)-アルキル、(C1-C4)-アルキルスルフィニル-(C1-C4)-アルキル、(C1-C4)-アルキルスルホニル-(C1-C4)-アルキル、(C1-C8)-アルキルカルボニル、(C1-C8)-ハロアルキルカルボニル、(C3-C8)-シクロアルキルカルボニル、カルボキシル、(C1-C8)-アルコキシカルボニル、(C1-C8)-ハロアルコキシカルボニル、(C3-C8)-シクロアルコキシカルボニル、(C1-C8)-アルキルアミノカルボニル、(C2-C8)-ジアルキルアミノカルボニル、(C3-C8)-シクロアルキルアミノカルボニル、ヒドロキシ、(C1-C8)-アルコキシ、(C1-C8)-ハロアルコキシ、(C1-C8)-アルキルチオ、(C1-C8)-ハロアルキルチオ、(C3-C8)-シクロアルキルチオ、(C1-C8)-アルキルスルフィニル、(C1-C8)-ハロアルキルスルフィニル、(C3-C8)-シクロアルキルスルフィニル、(C1-C8)-アルキルスルホニル、(C1-C8)-ハロアルキルスルホニル、(C3-C8)-シクロアルキルスルホニル、(C1-C8)-アルキルアミノスルホニル、(C2-C8)-ジアルキルアミノスルホニル又は(C3-C8)-トリアルキルシリルを表し、
R4及びR5は、他のものとは独立に、水素、ヒドロキシ、ハロゲン、(C1-C8)-アルキル、(C1-C8)-ハロアルキル、(C2-C8)-アルケニル、(C2-C8)-アルキニル、(C1-C4)-アルコキシ-(C1-C4)-アルキル、(C1-C4)-ハロアルコキシ-(C1-C4)-アルキル、(C1-C4)-アルキルチオ-(C1-C4)-アルキル、(C1-C4)-アルキルスルフィニル-(C1-C4)-アルキル、(C1-C4)-アルキルスルホニル-(C1-C4)-アルキル、(C1-C8)-アルキルカルボニル、(C1-C8)-ハロアルキルカルボニル、(C3-C8)-シクロアルキルカルボニル、(C1-C8)-アルコキシカルボニル、(C1-C8)-ハロアルコキシカルボニル、(C3-C8)-シクロアルコキシカルボニル、(C1-C8)-アルキルアミノカルボニル、(C2-C8)-ジアルキルアミノカルボニル、(C3-C8)-シクロアルキルアミノカルボニル、(C1-C8)-アルコキシ、(C1-C8)-アルキルチオ、(C1-C8)-ハロアルキルチオ、(C3-C8)-シクロアルキルチオを表し、
又は
R4及びR5は、一緒に3~6員炭素環又は最大2個の酸素原子を有する3~6員飽和複素環を形成し、
又は
R4及びR5は、一緒に(C1-C3)-アルキリデン基又は(C1-C3)-ハロアルキリデン基を形成し、
R6は、水素、(C1-C8)-アルキル、(C1-C8)-ハロアルキル、アリール-(C1-C6)-アルキル、ヘテロアリール-(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、(C3-C6)-ハロシクロアルキル、(C3-C6)-ハロシクロアルキル-(C1-C4)-アルキル、(C2-C8)-アルケニル、(C2-C8)-アルキニル、(C1-C4)-アルコキシ-(C1-C4)-アルキル、(C1-C4)-ハロアルコキシ-(C1-C4)-アルキル、(C1-C4)-アルキルチオ-(C1-C4)-アルキル、(C1-C4)-アルキルスルフィニル-(C1-C4)-アルキル、(C1-C4)-アルキルスルホニル-(C1-C4)-アルキル、(C1-C8)-アルキルカルボニル、(C1-C8)-ハロアルキルカルボニル、(C3-C8)-シクロアルキルカルボニル、ホルミル、(C1-C8)-アルコキシカルボニル、(C1-C8)-ハロアルコキシカルボニル、(C3-C8)-シクロアルコキシカルボニル、(C1-C8)-アルキルアミノカルボニル、(C2-C8)-ジアルキルアミノカルボニル、(C3-C8)-シクロアルキルアミノカルボニルを表し、そして
R7は、水素、ハロゲン、シアノ、ニトロ、ホルミル、(C1-C8)-アルキル、(C1-C8)-ハロアルキル、(C2-C8)-アルケニル、(C2-C8)-アルキニル、(C2-C8)-ハロアルケニル、(C2-C8)-ハロアルキニル、(C1-C4)-アルコキシ-(C1-C4)-アルキル、(C1-C4)-ハロアルコキシ-(C1-C4)-アルキル、(C1-C4)-アルキルチオ-(C1-C4)-アルキル、(C1-C4)-アルキルスルフィニル-(C1-C4)-アルキル、(C1-C4)-アルキルスルホニル-(C1-C4)-アルキル、(C1-C8)-アルキルカルボニル、(C1-C8)-ハロアルキルカルボニル、(C3-C8)-シクロアルキルカルボニル、カルボキシル、(C1-C8)-アルコキシカルボニル、(C1-C8)-ハロアルコキシカルボニル、(C3-C8)-シクロアルコキシカルボニル、(C1-C8)-アルキルアミノカルボニル、(C2-C8)-ジアルキルアミノカルボニル、(C3-C8)-シクロアルキルアミノカルボニル、ヒドロキシ、(C1-C8)-アルコキシ、(C1-C8)-ハロアルコキシ、(C1-C8)-アルキルチオ、(C1-C8)-ハロアルキルチオ、(C3-C8)-シクロアルキルチオ、(C1-C8)-アルキルスルフィニル、(C1-C8)-ハロアルキルスルフィニル、(C3-C8)-シクロアルキルスルフィニル、(C1-C8)-アルキルスルホニル、(C1-C8)-ハロアルキルスルホニル、(C3-C8)-シクロアルキルスルホニル、(C1-C8)-アルキルアミノスルホニル、(C2-C8)-ジアルキルアミノスルホニル又は(C3-C8)-トリアルキルシリルを表す。
Xが、窒素、-CF-又は-CH-を表し、
Aが、酸素、-S(O)n-、-C(R4)(R5)-、-C(=O)-又は-NR6-を表し、
n=0、1又は2であり、
R1が、置換されていても良いアリール、ヘテロアリール又は複素環を表し、ここで、各環若しくは各環系は、基R7から独立に選択される最大5個の置換基によって置換されていても良く、
R2が、他のものとは独立に、ハロゲン、シアノ、ニトロ、ホルミル、ホルムアミド、(C1-C6)-アルキル、(C1-C6)-ハロアルキル、(C2-C6)-アルケニル、(C2-C6)-アルキニル、(C2-C6)-ハロアルケニル、(C2-C6)-ハロアルキニル、(C1-C4)-アルコキシ-(C1-C4)-アルキル、(C1-C4)-ハロアルコキシ-(C1-C4)-アルキル、(C1-C4)-アルキルチオ-(C1-C4)-アルキル、(C1-C4)-アルキルスルフィニル-(C1-C4)-アルキル、(C1-C4)-アルキルスルホニル-(C1-C4)-アルキル、(C1-C6)-アルキルカルボニル、(C1-C6)-ハロアルキルカルボニル、(C3-C6)-シクロアルキルカルボニル、カルボキシル、(C1-C6)-アルコキシカルボニル、(C1-C6)-ハロアルコキシカルボニル、(C3-C6)-シクロアルコキシカルボニル、カルバモイル、(C2-C6)-アルキルアミノカルボニル、(C2-C8)-ジアルキルアミノカルボニル、(C3-C6)-シクロアルキルアミノカルボニル、(C1-C4)-アルコキシカルボニル-(C1-C4)-アルキル、(C1-C4)-ハロアルコキシカルボニル-(C1-C4)-アルキル、カルボキシ-(C1-C6)-アルキル、ヒドロキシ、アミノ、(C1-C6)-アルコキシ、(C1-C6)-ハロアルコキシ、(C1-C6)-アルキルチオ、(C1-C6)-ハロアルキルチオ、(C3-C6)-シクロアルキルチオ、(C1-C6)-アルキルスルフィニル、(C1-C6)-ハロアルキルスルフィニル、(C3-C6)-シクロアルキルスルフィニル、(C1-C6)-アルキルスルホニル、(C1-C6)-ハロアルキルスルホニル、(C3-C6)-シクロアルキルスルホニル、(C1-C6)-アルキルアミノスルホニル、(C2-C8)-ジアルキルアミノスルホニル又は(C3-C8)-トリアルキルシリルを表し、
mが、0、1、2又は3を表し、
R3が、水素、ハロゲン、シアノ、ニトロ、ホルミル、(C1-C6)-アルキル、(C1-C6)-ハロアルキル、(C2-C6)-アルケニル、(C2-C6)-アルキニル、(C2-C6)-ハロアルケニル、(C2-C6)-ハロアルキニル、(C1-C4)-アルコキシ-(C1-C4)-アルキル、(C1-C4)-ハロアルコキシ-(C1-C4)-アルキル、(C1-C4)-アルキルチオ-(C1-C4)-アルキル、(C1-C4)-アルキルスルフィニル-(C1-C4)-アルキル、(C1-C4)-アルキルスルホニル-(C1-C4)-アルキル、(C1-C6)-アルキルカルボニル、(C1-C6)-ハロアルキルカルボニル、(C3-C6)-シクロアルキルカルボニル、カルボキシル、(C1-C6)-アルコキシカルボニル、(C1-C6)-ハロアルコキシカルボニル、(C3-C6)-シクロアルコキシカルボニル、(C1-C6)-アルキルアミノカルボニル、(C2-C8)-ジアルキルアミノカルボニル、(C3-C6)-シクロアルキルアミノカルボニル、ヒドロキシ、(C1-C6)-アルコキシ、(C1-C6)-ハロアルコキシ、(C1-C6)-アルキルチオ、(C1-C6)-ハロアルキルチオ、(C3-C6)-シクロアルキルチオ、(C1-C6)-アルキルスルフィニル、(C1-C6)-ハロアルキルスルフィニル、(C3-C6)-シクロアルキルスルフィニル、(C1-C6)-アルキルスルホニル、(C1-C6)-ハロアルキルスルホニル、(C3-C6)-シクロアルキルスルホニル、(C1-C6)-アルキルアミノスルホニル、(C2-C8)-ジアルキルアミノスルホニル又は(C3-C8)-トリアルキルシリルを表し、
R4及びR5が、他のものとは独立に、水素、ヒドロキシ、ハロゲン、(C1-C6)-アルキル、(C1-C6)-ハロアルキル、(C2-C6)-アルケニル、(C2-C6)-アルキニル、(C1-C4)-アルコキシ-(C1-C4)-アルキル、(C1-C4)-ハロアルコキシ-(C1-C4)-アルキル、(C1-C4)-アルキルチオ-(C1-C4)-アルキル、(C1-C4)-アルキルスルフィニル-(C1-C4)-アルキル、(C1-C4)-アルキルスルホニル-(C1-C4)-アルキル、(C1-C6)-アルキルカルボニル、(C1-C6)-ハロアルキルカルボニル、(C3-C6)-シクロアルキルカルボニル、(C1-C6)-アルコキシカルボニル、(C1-C6)-ハロアルコキシカルボニル、(C3-C6)-シクロアルコキシカルボニル、(C1-C6)-アルキルアミノカルボニル、(C2-C8)-ジアルキルアミノカルボニル、(C3-C6)-シクロアルキルアミノカルボニル、(C1-C6)-アルコキシ、(C1-C6)-アルキルチオ、(C1-C6)-ハロアルキルチオ、(C3-C6)-シクロアルキルチオを表し、
又は
R4及びR5は、一緒に3~6員炭素環又は最大2個の酸素原子を有する3~6員飽和複素環を形成し、
又は
R4及びR5は、一緒に(C1-C3)-アルキリデン基又は(C1-C3)-ハロアルキリデン基を形成し、
R6が、水素、(C1-C6)-アルキル、(C1-C6)-ハロアルキル、アリール-(C1-C4)-アルキル、ヘテロアリール-(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-C4)-アルキル、(C3-C6)-ハロシクロアルキル、(C3-C6)-ハロシクロアルキル-(C1-C4)-アルキル、(C2-C6)-アルケニル、(C2-C6)-アルキニル、(C1-C4)-アルコキシ-(C1-C4)-アルキル、(C1-C4)-ハロアルコキシ-(C1-C4)-アルキル、(C1-C4)-アルキルチオ-(C1-C4)-アルキル、(C1-C4)-アルキルスルフィニル-(C1-C4)-アルキル、(C1-C4)-アルキルスルホニル-(C1-C4)-アルキル、(C1-C6)-アルキルカルボニル、(C1-C6)-ハロアルキルカルボニル、(C3-C6)-シクロアルキルカルボニル、ホルミル、(C1-C6)-アルコキシカルボニル、(C1-C6)-ハロアルコキシカルボニル、(C3-C6)-シクロアルコキシカルボニル、(C1-C6)-アルキルアミノカルボニル、(C2-C8)-ジアルキルアミノカルボニル、(C3-C8)-シクロアルキルアミノカルボニルを表し、そして
R7が、水素、ハロゲン、シアノ、ニトロ、ホルミル、(C1-C6)-アルキル、(C1-C6)-ハロアルキル、(C2-C6)-アルケニル、(C2-C6)-アルキニル、(C2-C6)-ハロアルケニル、(C2-C6)-ハロアルキニル、(C1-C4)-アルコキシ-(C1-C4)-アルキル、(C1-C4)-ハロアルコキシ-(C1-C4)-アルキル、(C1-C4)-アルキルチオ-(C1-C4)-アルキル、(C1-C4)-アルキルスルフィニル-(C1-C4)-アルキル、(C1-C4)-アルキルスルホニル-(C1-C4)-アルキル、(C1-C6)-アルキルカルボニル、(C1-C6)-ハロアルキルカルボニル、(C3-C6)-シクロアルキルカルボニル、カルボキシル、(C1-C6)-アルコキシカルボニル、(C1-C6)-ハロアルコキシカルボニル、(C3-C6)-シクロアルコキシカルボニル、(C1-C6)-アルキルアミノカルボニル、(C2-C8)-ジアルキルアミノカルボニル、(C3-C6)-シクロアルキルアミノカルボニル、ヒドロキシ、(C1-C6)-アルコキシ、(C1-C6)-ハロアルコキシ、(C1-C6)-アルキルチオ、(C1-C6)-ハロアルキルチオ、(C3-C6)-シクロアルキルチオ、(C1-C6)-アルキルスルフィニル、(C1-C6)-ハロアルキルスルフィニル、(C3-C6)-シクロアルキルスルフィニル、(C1-C6)-アルキルスルホニル、(C1-C6)-ハロアルキルスルホニル、(C3-C6)-シクロアルキルスルホニル、(C1-C6)-アルキルアミノスルホニル、(C2-C8)-ジアルキルアミノスルホニル又は(C3-C8)-トリアルキルシリルを表す、一般式(I)の化合物を提供する。
Xが、窒素、-CF-又は-CH-を表し、
Aが、酸素、-S(O)n-、-C(R4)(R5)-、-C(=O)-又は-NR6-を表し、
n=0、1又は2であり、
R1が、置換されていても良いアリール、ヘテロアリール又は複素環を表し、ここで、各環若しくは各環系は、基R7から独立に選択される最大5個の置換基によって置換されていても良く、
R2が、他のものとは独立に、ハロゲン、シアノ、ニトロ、ホルミル、ホルムアミド、(C1-C4)-アルキル、(C1-C4)-ハロアルキル、(C2-C4)-アルケニル、(C2-C4)-アルキニル、(C2-C4)-ハロアルケニル、(C1-C4)-アルコキシ-(C1-C4)-アルキル、(C1-C4)-ハロアルコキシ-(C1-C4)-アルキル、(C1-C4)-アルキルカルボニル、(C1-C4)-ハロアルキルカルボニル、カルボキシル、(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、(C3-C6)-シクロアルコキシカルボニル、カルバモイル、(C2-C4)-アルキルアミノカルボニル、(C2-C6)-ジアルキルアミノカルボニル、(C1-C4)-アルコキシカルボニル-(C1-C4)-アルキル、(C1-C4)-ハロアルコキシカルボニル-(C1-C4)-アルキル、カルボキシ-(C1-C4)-アルキル、ヒドロキシ、アミノ、(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)-アルキルスルフィニル、(C1-C4)-アルキルスルホニル、(C1-C4)-アルキルアミノスルホニル、(C2-C6)-ジアルキルアミノスルホニル又は(C3-C6)-トリアルキルシリルを表し、
mが、0、1、2又は3を表し、
R3が、水素、ハロゲン、シアノ、ニトロ、ホルミル、(C1-C4)-アルキル、(C1-C4)-ハロアルキル、(C2-C4)-アルケニル、(C2-C4)-アルキニル、(C2-C4)-ハロアルケニル、(C2-C4)-ハロアルキニル、(C1-C4)-アルキルカルボニル、(C1-C4)-ハロアルキルカルボニル、カルボキシル、(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、(C3-C6)-シクロアルコキシカルボニル、(C1-C4)-アルキルアミノカルボニル、(C2-C6)-ジアルキルアミノカルボニル、ヒドロキシ、(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)-ハロアルキルチオ、(C1-C4)-アルキルスルフィニル、(C1-C4)-ハロアルキルスルフィニル、(C1-C4)-アルキルスルホニル、(C1-C4)-ハロアルキルスルホニル、(C1-C4)-アルキルアミノスルホニル、(C2-C6)-ジアルキルアミノスルホニル又は(C3-C6)-トリアルキルシリルを表し、
R4及びR5が、他のものとは独立に、水素、ヒドロキシ、ハロゲン、(C1-C4)-アルキル、(C1-C4)-ハロアルキル、(C2-C4)-アルケニル、(C2-C4)-アルキニル、(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又は(C3-C6)-シクロアルコキシカルボニルを表し、
又は
R4及びR5は、一緒に(C1-C3)-アルキリデン基又は(C1-C3)-ハロアルキリデン基を形成し、
R6が、水素、(C1-C4)-アルキル、(C1-C4)-ハロアルキル、アリール-(C1-C4)-アルキル、ヘテロアリール-(C1-C4)-アルキル、(C2-C4)-アルケニル、(C2-C4)-アルキニル、(C1-C4)-アルキルカルボニル、ホルミル又は(C1-C4)-アルコキシカルボニルを表し、そして、
R7が、水素、ハロゲン、シアノ、ニトロ、ホルミル、(C1-C4)-アルキル、(C1-C4)-ハロアルキル、(C2-C4)-アルケニル、(C2-C4)-アルキニル、(C2-C4)-ハロアルケニル、(C2-C4)-ハロアルキニル、(C1-C4)-アルコキシ-(C1-C4)-アルキル、(C1-C4)-ハロアルコキシ-(C1-C4)-アルキル、(C1-C4)-アルキルカルボニル、(C1-C4)-ハロアルキルカルボニル、カルボキシル、(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、(C3-C6)-シクロアルコキシカルボニル、(C1-C4)-アルキルアミノカルボニル、(C2-C6)-ジアルキルアミノカルボニル、(C3-C6)-シクロアルキルアミノカルボニル、ヒドロキシ、(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)-ハロアルキルチオ、(C1-C4)-アルキルスルフィニル、(C1-C4)-ハロアルキルスルフィニル、(C1-C4)-アルキルスルホニル、(C1-C4)-ハロアルキルスルホニル、(C1-C4)-アルキルアミノスルホニル、(C2-C6)-ジアルキルアミノスルホニル又は(C3-C6)-トリアルキルシリルを表す、一般式(I)の化合物を提供する。
Xが、窒素、-CF-又は-CH-を表し、
Aが、酸素、-S(O)n-、-C(R4)(R5)-、-C(=O)-又は-NR6-を表し、
n=0、1又は2であり、
R1が、置換されていても良いフェニル、ピリジル又はピリミジルを表し、ここで、各環若しくは各環系は、基R7から独立に選択される最大5個の置換基によって置換されていても良く、
R2が、他のものとは独立に、ハロゲン、シアノ、(C1-C4)-アルキル、(C1-C4)-ハロアルキル、カルボキシル、(C1-C4)-アルコキシカルボニル、(C1-C4)-アルコキシカルボニル-(C1-C3)-アルキル、(C1-C4)-ハロアルコキシカルボニル-(C1-C3)-アルキル、カルボキシ-(C1-C3)-アルキル又は(C1-C4)-アルコキシを表し、
mが、0、1、2又は3を表し、
R3が、水素、ハロゲン、シアノ、(C1-C4)-アルキル、(C1-C4)-ハロアルキル、(C2-C4)-アルケニル、(C2-C4)-アルキニル、(C2-C4)-ハロアルケニル、(C2-C4)-ハロアルキニル、(C1-C4)-アルコキシ又は(C1-C4)-ハロアルコキシを表し、
R4及びR5が、他のものとは独立に、水素、ハロゲン、(C1-C4)-アルキル又は(C1-C4)-アルコキシカルボニルを表し、
R6が、水素、(C1-C4)-アルキル、(C1-C4)-アルキルカルボニル又は(C1-C4)-アルコキシカルボニルを表し、そして
R7が、水素、ハロゲン、シアノ、(C1-C4)-アルキル、(C1-C4)-ハロアルキル、カルボキシル、(C1-C4)-アルコキシカルボニル、ヒドロキシ、(C1-C4)-アルコキシ又は(C1-C4)-ハロアルコキシを表す、一般式(I)の化合物を提供する。
Xが、窒素、-CF-又は-CH-を表し、
Aが、酸素、硫黄、-CH2-又は-NR6-を表し、
R1が、置換されていても良いフェニル、ピリジル又はピリミジルを表し、ここで、各環若しくは各環系は、基R7から独立に選択される最大5個の置換基によって置換されていても良く、
R2が、他のものとは独立に、ハロゲン、シアノ、(C1-C4)-アルキル、(C1-C4)-ハロアルキル、カルボキシル、(C1-C4)-アルコキシカルボニル、(C1-C4)-アルコキシカルボニル-(C1-C3)-アルキル、(C1-C4)-ハロアルコキシカルボニル-(C1-C3)-アルキル、カルボキシ-(C1-C3)-アルキル又は(C1-C4)-アルコキシを表し、
mが、0、1、2又は3を表し、
R3が、水素、ハロゲン、シアノ、(C1-C4)-アルキル、(C1-C4)-ハロアルキル、(C1-C4)-アルコキシ又は(C1-C4)-ハロアルコキシを表し、
R6が水素又はメチルを表し、そして
R7が、水素、ハロゲン、シアノ、(C1-C4)-アルキル、(C1-C4)-ハロアルキル、(C1-C4)-アルコキシ又は(C1-C4)-ハロアルコキシを表す、一般式(I)の化合物を提供する。
Xが、-CH-、-CF-又は窒素を表し、
Aが、酸素、硫黄、-CH2-又は-NR6-を表し、
R1が、置換されていても良いフェニル、ピリジ-2-イル又はピリミジ-2-イルを表し、ここで、各環は、基R7から互いに独立に選択される最大5個の置換基によって置換されていても良く、
R2が、他のものとは独立に、フッ素、塩素、臭素、シアノ、メチル、エチル、トリフルオロメチル、メトキシ、メトキシカルボニルメチル、カルボキシルメチルを表し、
mが、0、1、2又は3を表し、
R3が、水素、フッ素、塩素、シアノ、メチル、トリフルオロメチル、メトキシ、トリフルオロメトキシを表し、
R6が、水素又はメチルを表し、そして
R7が、水素、フッ素、塩素、臭素、シアノ、メチル、トリフルオロメチル、メトキシ、トリフルオロメトキシを表す、一般式(I)の化合物を提供する。
Xが、-CH-、-CF-又は窒素を表し、
Aが、酸素、硫黄、-CH2-又は-NH-を表し、
R1が、フェニル、4-フルオロフェニル、2、4-ジフルオロフェニル、3、4-ジフルオロフェニル、3-(トリフルオロメチル)フェニル、3-メトキシフェニル、3-クロロフェニル、4-クロロフェニル、4-シアノフェニル、4-メチルフェニル、3-フルオロ-4-メチルフェニル、4-フルオロ-3-メチルフェニル、2、4-ジフルオロ-3-メトキシフェニル、5-クロロ-3-フルオロピリジ-2-イル、5-クロロピリジ-2-イル、5-フルオロピリジ-2-イル、3、5-ジフルオロピリジ-2-イル、5-フルオロピリミジ-2-イル、5-クロロピリミジ-2-イルを表し;
R2が、メチルを表し、
mが、0、1又は2を表し、そして
R3が、水素、フッ素、塩素、トリフルオロメチルを表す、一般式(I)の化合物を提供する。
-1,3-オキサジン-2-又は-4-又は-5-又は-6-イル;4H-1,3-オキサジン-2-又は-4-又は-5-又は-6-イル;モルホリン-2-又は-3-又は-4-イル;3,4-ジヒドロ-2H-1,4-オキサジン-2-又は-3-又は-4-又は-5-又は-6-イル;3,6-ジヒドロ-2H-1,4-オキサジン-2-又は-3-又は-5-又は-6-イル;2H-1,4-オキサジン-2-又は-3-又は-5-又は-6-イル;4H-1,4-オキサジン-2-又は-3-イル;1,2-オキサゼパン-2-又は-3-又は-4-又は-5-又は-6-又は-7-イル;2,3,4,5-テトラヒドロ-1,2-オキサゼピン-2-又は-3-又は-4-又は-5-又は-6-又は-7-イル;2,3,4,7-テトラヒドロ-1,2-オキサゼピン-2-又は-3-又は-4-又は-5-又は-6-又は-7-イル;2,3,6,7-テトラヒドロ-1,2-オキサゼピン-2-又は-3-又は-4-又は-5-又は-6-又は-7-イル;2,5,6,7-テトラヒドロ-1,2-オキサゼピン-2-又は-3-又は-4-又は-5-又は-6-又は-7-イル;4,5,6,7-テトラヒドロ-1,2-オキサゼピン-3-又は-4-又は-5-又は-6-又は-7-イル;2,3-ジヒドロ-1,2-オキサゼピン-2-又は-3-又は-4-又は-5-又は-6-又は-7-イル;2,5-ジヒドロ-1,2-オキサゼピン-2-又は-3-又は-4-又は-5-又は-6-又は-7-イル;2,7-ジヒドロ-1,2-オキサゼピン-2-又は-3-又は-4-又は-5-又は-6-又は-7-イル;4,5-ジヒドロ-1,2-オキサゼピン-3-又は-4-又は-5-又は-6-又は-7-イル;4,7-ジヒドロ-1,2-オキサゼピン-3-又は-4-又は-5-又は-6-又は-7-イル;6,7-ジヒドロ-1,2-オキサゼピン-3-又は-4-又は-5-又は-6-又は-7-イル;1,2-オキサゼピン-3-又は-4-又は-5-又は-6-又は-7-イル;1,3-オキサゼパン-2-又は-3-又は-4-又は-5-又は-6-又は-7-イル;2,3,4,5-テトラヒドロ-1,3-オキサゼピン-2-又は-3-又は-4-又は-5-又は-6-又は-7-イル;2,3,4,7-テトラヒドロ-1,3-オキサゼピン-2-又は-3-又は-4-又は-5-又は-6-又は-7-イル;2,3,6,7-テトラヒドロ-1,3-オキサゼピン-2-又は-3-又は-4-又は-5-又は-6-又は-7-イル;2,5,6,7-テトラヒドロ-1,3-オキサゼピン-2-又は-4-又は-5-又は-6-又は-7-イル;4,5,6,7-テトラヒドロ-1,3-オキサゼピン-2-又は-4-又は-5-又は-6-又は-7-イル;2,3-ジヒドロ-1,3-オキサゼピン-2-又は-3-又は-4-又は-5-又は-6-又は-7-イル;2,5-ジヒドロ-1,3-オキサゼピン-2-又は-4-又は-5-又は-6-又は-7-イル;2,7-ジヒドロ-1,3-オキサゼピン-2-又は-4-又は-5-又は-6-又は-7-イル;4,5-ジヒドロ-1,3-オキサゼピン-2-又は-4-又は-5-又は-6-又は-7-イル;4,7-ジヒドロ-1,3-オキサゼピン-2-又は-4-又は-5-又は-6-又は-7-イル;6,7-ジヒドロ-1,3-オキサゼピン-2-又は-4-又は-5-又は-6-又は-7-イル;1,3-オキサゼピン-2-又は-4-又は-5-又は-6-又は-7-イル;1,4-オキサゼパン-2-又は-3-又は-5-又は-6-又は-7-イル;2,3,4,5-テトラヒドロ-1,4-オキサゼピン-2-又は-3-又は-4-又は-5-又は-6-又は-7-イル;2,3,4,7-テトラヒドロ-1,4-オキサゼピン-2-又は-3-又は-4-又は-5-又は-6-又は-7-イル;2,3,6,7-テトラヒドロ-1,4-オキサゼピン-2-又は-3-又は-5-又は-6-又は-7-イル;2,5,6,7-テトラヒドロ-1,4-オキサゼピン-2-又は-3-又は-5-又は-6-又は-7-イル;4,5,6,7-テトラヒドロ-1,4-オキサゼピン-2-又は-3-又は-4-又は-5-又は-6-又は-7-イル;2,3-ジヒドロ-1,4-オキサゼピン-2-又は-3-又は-5-又は-6-又は-7-イル;2,5-ジヒドロ-1,4-オキサゼピン-2-又は-3-又は-5-又は-6-又は-7-イル;2,7-ジヒドロ-1,4-オキサゼピン-2-又は-3-又は-5-又は-6-又は-7-イル;4,5-ジヒドロ-1,4-オキサゼピン-2-又は-3-又は-4-又は-5-又は-6-又は-7-イル;4,7-ジヒドロ-1,4-オキサゼピン-2-又は-3-又は-4-又は-5-又は-6-又は-7-イル;6,7-ジヒドロ-1,4-オキサゼピン-2-又は-3-又は-5-又は-6-又は-7-イル;1,4-オキサゼピン-2-又は-3-又は-5-又は-6-又は-7-イル;イソチアゾリジン-2-又は-3-又は-4-又は-5-イル;2,3-ジヒドロイソチアゾール-2-又は-3-又は-4-又は-5-イル;2,5-ジヒドロイソチアゾール-2-又は-3-又は-4-又は-5-イル;4,5-ジヒドロイソチアゾール-3-又は-4-又は-5-イル;1,3-チアゾリジン-2-又は-3-又は-4-又は-5-イル;2,3-ジヒドロ-1,3-チアゾール-2-又は-3-又は-4-又は-5-イル;2,5-ジヒドロ-1,3-チアゾール-2-又は-4-又は-5-イル;4,5-ジヒドロ-1,3-チアゾール-2-又は-4-又は-5-イル;1,3-チアジナン-2-又は-3-又は-4-又は-5-又は-6-イル;3,4-ジヒドロ-2H-1,3-チアジン-2-又は-3-又は-4-又は-5-又は-6-イル;3,6-ジヒドロ-2H-1,3-チアジン-2-又は-3-又は-4-又は-5-又は-6-イル;5,6-ジヒドロ-2H-1,3-チアジン-2-又は-4-又は-5-又は-6-イル;5,6-ジヒドロ-4H-1,3-チアジン-2-又は-4-又は-5-又は-6-イル;2H-1,3-チアジン-2-又は-4-又は-5-又は-6-イル;6H-1,3-チアジン-2-又は-4-又は-5-又は-6-イル;4H-1,3-チアジン-2-又は-4-又は-5-又は-6-イルである。「複素環」のさらなる例は、N、O及びSの群からの3個のヘテロ原子を有する部分若しくは完全水素化複素環基であり、例えば1,4,2-ジオキサゾリジン-2-又は-3-又は-5-イル;1,4,2-ジオキサゾール-3-又は-5-イル;1,4,2-ジオキサジナン-2-又は-3-又は-5-又は-6-イル;5,6-ジヒドロ-1,4,2-ジオキサジン-3-又は-5-又は-6-イル;1,4,2-ジオキサジン-3-又は-5-又は-6-イル;1,4,2-ジオキサゼパン-2-又は-3-又は-5-又は-6-又は-7-イル;6,7-ジヒドロ-5H-1,4,2-ジオキサゼピン-3-又は-5-又は-6-又は-7-イル;2,3-ジヒドロ-7H-1,4,2-ジオキサゼピン-2-又は-3-又は-5-又は-6-又は-7-イル;2,3-ジヒドロ-5H-1,4,2-ジオキサゼピン-2-又は-3-又は-5-又は-6-又は-7-イル;5H-1,4,2-ジオキサゼピン-3-又は-5-又は-6-又は-7-イル;7H-1,4,2-ジオキサゼピン-3-又は-5-又は-6-又は-7-イルである。さらに置換されていても良い複素環の構造例も、下記に挙げる。
一般式(Ia)のピリジン類は、亜鉛(0)及びパラジウム触媒(例えば、Pd(dppf)Cl2・CH2Cl2)、又は、銅(0)及び塩基の存在下に、LGが脱離基を表すピリジン類(E-III)を、ジスルフィド(E-IV)とカップリングさせることで製造することができる。塩基は、アルカリ金属(例えば、ナトリウム又はカリウム)の酢酸塩であることができる。その反応は、通常、有機溶媒、例えばテトラヒドロフラン、ジメチルスルホキシド又はジメチルホルムアミド中、0℃から溶媒の沸点までの温度で行う。
一般式(Ib)のスルホン類及びスルホキシド類は、ピリジン類(Ia)の酸化によって製造することができる。そのような反応は当業者によって知られており、例えば、Advanced Synthesis&Catalysis(2011),353(2+3),295-302に記載されている。
一般式(Ic)のピリジン類は、パラジウム触媒(例えばPd(PPh3)4)及び塩基の存在下に、ピリジン類(E-VII)を、Halがハロゲンを表すアルキルハライド(E-VIII)とカップリングさせることで製造することができる。その塩基は、アルカリ金属(例えばナトリウム又はカリウム)の炭酸塩であることができる。その反応は、通常、有機溶媒、例えば水を含有する若しくは含有しないテトラヒドロフラン、トルエン又はエタノール中、0℃から溶媒の沸点までの温度で行う。
一般式(Id)のピリジン類は、塩基の存在下に、ピリジン類(E-XII)を、LGが脱離基を表すピリ(ミ)ジン(E-II)及び銅(I)塩でアルキル化することで製造することができる。その塩基は、アルカリ金属(例えばナトリウム、カリウム又はセシウム)の炭酸塩であることができる。その銅塩は、銅ハライド、例えばヨウ化銅(I)であることができる。その反応は、通常、有機溶媒、例えばアセトニトリル又はジメチルホルムアミド中、0℃から溶媒の沸点までの温度で行う。
NMRピークリスト法
選択された実施例の1H NMRデータは、1H-NMRピークリストの形態で記載される。各シグナルピークについて、最初にδ値(ppm単位)と次に小括弧内のシグナル強度が列記されている。異なるシグナルピークについてのδ値-シグナル強度数値のペアは、セミコロンによって互いに分離されて列記されている。
鋭いシグナルの強度は、cm単位でのNMRスペクトラムのプリント例におけるシグナルの高さと相関しており、シグナル強度の真の比を示す。広いシグナルの場合、いくつかのピーク若しくはそのシグナルの中央並びにそれの相対強度を、スペクトラム中の最も強いシグナルとの比較で示すことができる。
-1以上の上記で定義の一般式(I)の化合物及び/又はその塩、好ましくは、好ましい若しくは特に好ましいと確認される実施形態の一つでの、特には、上記で定義の各場合での式(I-001)~(I-662)の1以上の化合物及び/又はその塩、又は
-下記で定義の本発明による組成物
を、(有害)植物、(有害)植物の種子、(有害)植物が中で又は上で成長する土壌又は耕作中の区画に施用することを特徴とする方法を提供する。
-1以上の上記で定義の一般式(I)の化合物及び/又はその塩、好ましくは、好ましい若しくは特に好ましいと確認される実施形態の一つでの、特には、上記で定義の各場合での式(I-001)~(I-662)の1以上の化合物及び/又はその塩、又は
-下記で定義の本発明による組成物
を、望ましくない植物(例えば、単子葉若しくは双子葉雑草又は望ましくない作物植物などの有害植物)、望ましくない植物の種子(即ち、植物種子、例えば穀粒、種子又は栄養繁殖器官、例えば塊茎又は芽を有する若枝部)、望ましくない植物が中で若しくは上で成長する土壌(例えば、耕作地又は非耕作地の土壌)又は耕作中の区画(即ち、望ましくない植物が成長する区画)に施用することを特徴とする方法を提供する。
-1以上の上記で定義の一般式(I)の化合物及び/又はその塩、好ましくは、好ましい若しくは特に好ましいと確認される実施形態の一つでの、特には、上記で定義の各場合での式(I-001)~(I-662)の1以上の化合物及び/又はその塩、又は
-下記で定義の本発明による組成物
を、植物、植物の種子(即ち、植物種子、例えば穀粒、種子又は栄養繁殖器官、例えば塊茎又は芽を有する若枝部)、植物が中で若しくは上で成長する土壌(例えば、耕作地又は非耕作地の土壌)又は耕作中の区画(即ち、植物が成長する区画)に施用することを特徴とする方法を提供する。
(a)1以上の上記で定義の一般式(I)の化合物及び/又はその塩、好ましくは、好ましい若しくは特に好ましいと確認された実施形態の一つでの、特には上記で定義の各場合での1以上の式(I-001)~(I-662)の化合物及び/又はその塩、
及び
(b)下記の群(i)及び/又は(ii)から選択される1以上のさらなる物質:
(i)1以上のさらに別の農薬活性物質、好ましくは殺虫剤、殺ダニ剤、殺線虫剤、さらに別の除草剤(即ち、上記で定義の一般式(I)に一致しないもの)、殺菌剤、薬害軽減剤、肥料、及び/又は、さらに別の成長調節剤から選択されるもの、
(ii)作物保護で慣用の1以上の製剤補助剤。
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、ブラシノリド、カテコール、クロロメクワットクロライド、クロプロップ、シクラニリド、3-(シクロプロプ-1-エンイル)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、メピコートクロライド、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-エチル、チトデフ(tsitodef)、ウニコナゾール、ウニコナゾール-Pである。
S1a)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)、好ましくは下記のような化合物、
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、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(S1-1)(「メフェンピル-ジエチル」)、及びWO-A-91/07874に記載の関連する化合物;
S1b)ジクロロフェニルピラゾールカルボン酸の誘導体(S1b)、
好ましくは下記のような化合物、
1-(2,4-ジクロロフェニル)-5-メチルピラゾール-3-カルボン酸エチル(S1-2)、1-(2,4-ジクロロフェニル)-5-イソプロピルピラゾール-3-カルボン酸エチル(S1-3)、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-カルボン酸エチル(S1-4)及びEP-A-333131及びEP-A-269806に記載の関連化合物;
S1c)1,5-ジフェニルピラゾール-3-カルボン酸の誘導体(S1c)、
好ましくは下記のような化合物、
1-(2,4-ジクロロフェニル)-5-フェニルピラゾール-3-カルボン酸エチル(S1-5)、1-(2-クロロフェニル)-5-フェニルピラゾール-3-カルボン酸メチル(S1-6)、及び例えばEP-A-268554に記載の関連化合物;
S1d)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)のような化合物、即ち
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-カルボン酸エチル(S1-7)、及びEP-A-174562及びEP-A-346620に記載の関連化合物;
S1e)5-ベンジル-又は5-フェニル-2-イソオキサゾリン-3-カルボン酸型、又は5,5-ジフェニル-2-イソオキサゾリン-3-カルボン酸型(S1e)の化合物、
好ましくは下記のような化合物、
5-(2,4-ジクロロベンジル)-2-イソオキサゾリン-3-カルボン酸エチル(S1-8)又は5-フェニル-2-イソオキサゾリン-3-カルボン酸エチル(S1-9)及びWO-A-91/08202に記載の関連化合物、又は5,5-ジフェニル-2-イソオキサゾリンカルボン酸(S1-10)又は特許出願WO-A-95/07897に記載の5,5-ジフェニル-2-イソオキサゾリン-3-カルボン酸エチル(S1-11)(「イソキサジフェン-エチル」)又は5,5-ジフェニル-2-イソオキサゾリン-3-カルボン酸n-プロピル(S1-12)又は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-カルボン酸エチル(S1-13)の化合物、
S2)8-キノリノキシ誘導体(S2)の群からの化合物:
S2a)8-キノリニノキシ酢酸型の化合物(S2a)、好ましくは(5-クロロ-8-キノリニノキシ)酢酸1-メチルヘキシル(「クロキントセット-メキシル」)(S2-1)、(5-クロロ-8-キノリニノキシ)酢酸1,3-ジメチルブト-1-イル(S2-2)、(5-クロロ-8-キノリニノキシ)酢酸4-アリルオキシブチル(S2-3)、(5-クロロ-8-キノリニノキシ)酢酸1-アリルオキシプロプ-2-イル(S2-4)、(5-クロロ-8-キノリニノキシ)酢酸エチル(S2-5)、(5-クロロ-8-キノリニノキシ)酢酸メチル(S2-6)、(5-クロロ-8-キノリニノキシ)酢酸アリル(S2-7)、(5-クロロ-8-キノリニノキシ)酢酸2-(2-プロピリデンイミノキシ)-1-エチル(S2-8)、(5-クロロ-8-キノリニノキシ)酢酸2-オキソプロプ-1-イル(S2-9)及びEP-A-86750、EP-A-94349及びEP-A-191736又はEP-A-0492366に記載の関連化合物、さらにはWO-A-2002/34048に記載の(5-クロロ-8-キノリニノキシ)酢酸(S2-10)、それ水和物及び塩、例えばそのリチウム、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、スルホニウム又はホスホニウム塩;
S2b)(5-クロロ-8-キノリニノキシ)マロン酸型の化合物(S2b)、好ましくは(5-クロロ-8-キノリニノキシ)マロン酸ジエチル、(5-クロロ-8-キノリニノキシ)マロン酸ジアリル、(5-クロロ-8-キノリニノキシ)マロン酸メチルエチルのような化合物及びEP-A-0582198に記載の関連化合物。
「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からの「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からの「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からの「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からの「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又はMonsantoからの「AD-67」又は「MON4660」(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からの「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))又はBASFからの「BAS145138」又は「LAB145138」(S3-9)((RS)-1-ジクロロアセチル-3,3,8a-トリメチルパーヒドロピロロ[1,2-a]ピリミジン-6-オン、「フリラゾール(furilazole)」又は「MON13900」((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)、及びその(R)異性体(S3-11)。
RA 1は、(C1-C6)-アルキル、(C3-C6)-シクロアルキルを表し、後者の二つの基は、ハロゲン、(C1-C4)-アルコキシ、(C1-C6)-ハロアルコキシ及び(C1-C4)-アルキルチオの群からのvA個の置換基によって、環状基の場合は、(C1-C4)-アルキル及び(C1-C4)-ハロアルキルによっても置換されており;
RA 2は、ハロゲン、(C1-C4)-アルキル、(C1-C4)-アルコキシ、CF3を表し;
mAは、1又は2を表し;
vAは、0、1、2又は3を表す。
RB 1、RB 2は、互いに独立に、水素、(C1-C6)-アルキル、(C3-C6)-シクロアルキル、(C3-C6)-アルケニル、(C3-C6)-アルキニルを表し、
RB 3は、ハロゲン、(C1-C4)-アルキル、(C1-C4)-ハロアルキル又は(C1-C4)-アルコキシを表し、
mBは、1又は2を表し、
RB 1=シクロプロピル、RB 2=水素及び(RB 3)=2-OMe(「シプロスルファミド」、S4-1)、
RB 1=シクロプロピル、RB 2=水素及び(RB 3)=5-Cl-2-OMe(S4-2)、
RB 1=エチル、RB 2=水素及び(RB 3)=2-OMe(S4-3)、
RB 1=イソプロピル、RB 2=水素及び(RB 3)=5-Cl-2-OMe(S4-4)、及び
RB 1=イソプロピル、RB 2=水素及び(RB 3)=2-OMe(S4-5)。
RC 1、RC 2は、互いに独立に、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、
RC 3は、ハロゲン、(C1-C4)-アルキル、(C1-C4)-アルコキシ及びCF3を表し、
mCは1又は2を表し:
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、
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。
RD 4は、ハロゲン、(C1-C4)-アルキル、(C1-C4)-アルコキシ、CF3を表し;
mDは、1又は2を表し;
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)-シクロアルケニルを表す。
RD 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)-ハロアルコキシを表し、
RD 2は、水素又は(C1-C4)-アルキルを表し、
RD 3は、水素、(C1-C8)-アルキル、(C2-C4)-アルケニル、(C2-C4)-アルキニル又はアリールを表し、上記の炭素含有基のそれぞれは、置換されていないかハロゲン及びアルコキシからなる群からの1以上、好ましくは3個以下の同一もしくは異なる基によって置換されており;
nDは0~2の整数を表す。
RE 1は、ハロゲン、(C1-C4)-アルキル、メトキシ、ニトロ、シアノ、CF3、OCF3を表し、
YE、ZEは、互いに独立にO又はSを表し、
nEは、0~4の整数を表し、
RE 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、ハロベンジルを表し、
RE 3は、水素又は(C1-C6)アルキルを表す。
オオムギがメトラクロール損傷に対抗するため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)、
キビ/モロコシがメトラクロール損傷に対抗するため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)、及び
キビ/モロコシがメトラクロール損傷に対抗するための種子粉衣薬害軽減剤として知られる「シオメトリニル」又は「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)。
トウモロコシがチオカーバメート除草剤損傷に対抗するための種子粉衣薬害軽減剤として知られる「ナフタリン酸無水物」(1,8-ナフタリンジカルボン酸無水物)(S13-1)、
播種したイネでのプレチラクロール用の薬害軽減剤として知られる「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)、
キビ/モロコシがアラクロール及びメトラクロル損傷に対抗するための種子粉衣薬害軽減剤として知られる「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)
「CL304415」(CAS登録番号31541-57-8)
トウモロコシがイミダゾリノン類による損傷に対抗するための薬害軽減剤として知られるAmerican Cyanamidからの(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)、
トウモロコシ用薬害軽減剤として知られるNitrokemiaからの「MG191」(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からの(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)、
「ジエトラート」(O,O-ジエチルO-フェニルホスホロチオエート)(S13-8)、
「メフェナート」(4-クロロフェニルメチルカーバメート)(S13-9)。
除草剤モリネートによる損傷に対抗するイネ用薬害軽減剤として知られる「ジメピペラート」又は「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除草剤による損傷に対抗するイネ用薬害軽減剤として知られる「ダイムロン」又は「SK23」(1-(1-メチル-1-フェニルエチル)-3-p-トリル尿素)、
一部の除草剤による損傷に対抗するイネ用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、JP-A-60087254参照)、
イネが一部の除草剤による損傷に対抗するイネ用薬害軽減剤として知られる「メトキシフェノン」又は「NK049」(3,3′-ジメチル-4-メトキシベンゾフェノン)、
イネにおいて一部の除草剤による損傷対抗する薬害軽減剤として知られるKumiaiからの「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)。
RH 1は、(C1-C6)-ハロアルキル基を表し、
RH 2は、水素又はハロゲンを表し、
RH 3、RH 4は、互いに独立に、水素、(C1-C16)-アルキル、(C2-C16)-アルケニル又は(C2-C16)-アルキニルを表し、ここで、後者の三つの基のそれぞれは、置換されていないか、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、置換されていない又は置換されている(C3-C6)-シクロアルキル、置換されていない又は置換されているフェニル、及び置換されていない又は置換されている複素環の群からの1以上の基によって置換されており、
又は環の一方の側で4~6員の飽和もしくは不飽和炭素環に縮合した(C3-C6)-シクロアルキル、(C4-C6)-シクロアルケニル、(C3-C6)-シクロアルキル、又は環の一方の側で4~6員の飽和もしくは不飽和炭素環に縮合した(C4-C6)-シクロアルケニルを表し、ここで、後者の四つの基のそれぞれは、置換されていないか、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、置換されていない又は置換されている(C3-C6)-シクロアルキル、置換されていない又は置換されているフェニル、及び置換されていない又は置換されている複素環の群からの1以上の基によって置換されており、
又は
RH 3は、(C1-C4)-アルコキシ、(C2-C4)-アルケニルオキシ、(C2-C6)-アルキニルオキシ又は(C2-C4)-ハロアルコキシを表し、
RH 4は、水素又は(C1-C4)-アルキルを表し、又は
RH 3及びRH 4は、直接結合した窒素原子と一体となって、4~8員のヘテロ環を表し、その環はその窒素原子以外にN、O及びSの群からの別の環ヘテロ原子、好ましくは2個以下の別の環ヘテロ原子を含んでいても良く、置換されていないか、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)-ハロアルコキシ及び(C1-C4)-アルキルチオの群からの1以上の基によって置換されている。
(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(ラクチジクロール(lactidichlor)-エチル)。
A.早期発芽後除草作用
単子葉又は双子葉雑草植物の種子を96ウェルマイクロタイタープレート中ケイ砂に入れ、制御された成長条件下で温度/湿度調節室で成長させた。播種から5~7日後に、試験植物を子葉段階で処理した。乳剤(EC)の形態で製剤された本発明による化合物を、2200リットル/ha相当量の水施用量で施用した。試験植物を至適成長条件下で9~12日にわたって温度/湿度調節室中に放置しておいた後、調製液の効果を、未処理対照と比較して肉眼的に評点した。例えば、100%活性=植物が枯死、0%活性=対照植物同様。
単子葉及び双子葉雑草植物の種子を、プラスチック製ポット中、砂壌土に入れ(各場合で、ポット当たり単子葉雑草植物又は双子葉雑草植物のうちの一方の植物を二連で播種)、土壌で覆い、制御された成長条件下の温室中で栽培した。播種から2~3週間後、試験植物は、一葉段階で処理した。水和剤(WP)の形態で又は乳剤(EC)として製剤された本発明の化合物を、水施用量600リットル/ha(換算)で0.5%添加剤を加えた水系懸濁液若しくは乳濁液として植物の緑色部分に施用した。試験植物を、約3週間にわたり至適な成長条件下で温室中に維持した後、調製液の活性を、未処理対照と比較して肉眼的に評点した。例えば、100%活性=植物が枯死、0%活性=対照植物同様。
単子葉及び双子葉雑草植物の種子を、プラスチック製ポット中、砂壌土に入れ(各場合で、ポット当たり単子葉雑草植物又は双子葉雑草植物のうちの一方の植物を二連で播種)、土壌で覆った。水和剤(WP)の形態で又は乳剤(EC)として製剤された本発明の化合物を、水施用量600リットル/ha(換算)で0.5%添加剤を加えた水系懸濁液若しくは乳濁液として被覆土壌の表面上に施用した。処理後、ポットを温室に入れ、試験植物に良好な成長条件下に維持した。約3週間後、調製液の活性を、未処理対照と比較してパーセントとして肉眼的に評点した。例えば、100%活性=植物が枯死、0%活性=対照植物同様。
Claims (11)
- 下記一般式(I)の置換2-ヘテロアリールオキシピリジン又はその塩。
Xは、-CH-、-CF-又は窒素を表し、
Aは、酸素、硫黄、-CH 2 -又は-NR 6 -を表し、
R1は、置換されていても良いフェニル、ピリジ-2-イル又はピリミジ-2-イルを表し、ここで、各環は、基R 7 から互いに独立に選択される最大5個の置換基によって置換されていても良く;
R2は、他のものとは独立に、フッ素、塩素、臭素、シアノ、メチル、エチル、トリフルオロメチル、メトキシ、メトキシカルボニルメチル、カルボキシルメチルを表し;
mは、0、1、2又は3を表し、
R3は、水素、フッ素、塩素、シアノ、メチル、トリフルオロメチル、メトキシ、トリフルオロメトキシを表し、
R 6は、水素又はメチルを表し、そして
R7は、水素、フッ素、塩素、臭素、シアノ、メチル、トリフルオロメチル、メトキシ、トリフルオロメトキシを表す。] - 除草活性量の少なくとも一つの請求項1に記載の一般式(I)の化合物であることを特徴とする除草剤組成物。
- 製剤補助剤との混合物中にある請求項2に記載の除草剤組成物。
- 殺虫剤、殺ダニ剤、除草剤、殺菌剤、薬害軽減剤及び成長調節剤からなる群からの少なくとも一つのさらなる農薬活性物質を含む、請求項2又は3に記載の除草剤組成物。
- 薬害軽減剤を含む、請求項4に記載の除草剤組成物。
- シプロスルファミド、クロキントセット-メキシル、メフェンピル-ジエチル又はイソキサジフェン-エチルを含む、請求項5に記載の除草剤組成物。
- さらなる除草剤を含む、請求項2~6のいずれか1項に記載の除草剤組成物。
- 望ましくない植物を防除する方法であって、有効量の少なくとも一つの請求項1に記載の一般式(I)の化合物又は請求項2~7のいずれか1項に記載の除草剤組成物を、当該植物に又は望ましくない植生の場所に施用することを特徴とする方法。
- 望ましくない植物の防除のための、請求項1に記載の一般式(I)の化合物又は請求項2~7のいずれか1項に記載の除草剤組成物の使用。
- 前記一般式(I)の化合物を、有用植物の作物における望ましくない植物の防除に使用する、請求項9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、請求項10に記載の使用。
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PCT/EP2019/066197 WO2020002089A1 (de) | 2018-06-25 | 2019-06-19 | Substituierte 2-heteroaryloxypyridine sowie deren salze und ihre verwendung als herbizide wirkstoffe |
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EP (1) | EP3810589A1 (ja) |
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EP3810588A1 (de) * | 2018-06-25 | 2021-04-28 | Bayer Aktiengesellschaft | Substituierte 4-heteroaryloxypyridine sowie deren salze und ihre verwendung als herbizide wirkstoffe |
WO2022002838A1 (de) | 2020-06-30 | 2022-01-06 | Bayer Aktiengesellschaft | Substituierte heteroaryloxypyridine sowie deren salze und ihre verwendung als herbizide wirkstoffe |
EP4052670A1 (fr) | 2021-03-02 | 2022-09-07 | AB Medica | Instrument pour souffler un gaz dans un organe vivant pour favoriser une dissection médicale de cet organe |
CN114190189A (zh) * | 2021-11-18 | 2022-03-18 | 山东元泰生物工程有限公司 | 一种能够促进植物生长的方法 |
WO2023186691A1 (de) | 2022-03-28 | 2023-10-05 | Bayer Aktiengesellschaft | Substituierte 2-c-azine sowie deren salze und ihre verwendung als herbizide wirkstoffe |
WO2023186690A1 (de) | 2022-03-28 | 2023-10-05 | Bayer Aktiengesellschaft | Substituierte 2-aminoazine sowie deren salze und ihre verwendung als herbizide wirkstoffe |
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JP2002533443A (ja) | 1998-12-23 | 2002-10-08 | シンジェンタ パーティシペーションズ アクチェンゲゼルシャフト | 置換型ピリジン除草剤 |
WO2004035564A1 (en) | 2002-10-17 | 2004-04-29 | Syngenta Participations Ag | Pyridine derivatives useful as herbicides |
WO2016149315A1 (en) | 2015-03-18 | 2016-09-22 | E. I. Du Pont De Nemours And Company | Substituted pyrimidinyloxy pyridine derivatives as herbicides |
WO2016196606A1 (en) | 2015-06-05 | 2016-12-08 | E I Du Pont De Nemours And Company | 2-(phenyloxy or phenylthio)pyrimidine derivatives as herbicides |
WO2017011288A1 (en) | 2015-07-13 | 2017-01-19 | E I Du Pont De Nemours And Company | Aryloxypyrimidinyl ethers as herbicides |
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AR115629A1 (es) | 2021-02-10 |
JP2021528448A (ja) | 2021-10-21 |
CN112469712A (zh) | 2021-03-09 |
EP3810589A1 (de) | 2021-04-28 |
US20210276974A1 (en) | 2021-09-09 |
EA202190111A1 (ru) | 2021-04-23 |
WO2020002089A1 (de) | 2020-01-02 |
CA3105217A1 (en) | 2020-01-02 |
US11834434B2 (en) | 2023-12-05 |
AU2019294743A1 (en) | 2021-01-14 |
BR112020025919A2 (pt) | 2021-03-16 |
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