TWI612045B - 作為殺真菌劑的哌啶吡唑類 - Google Patents

Info

Publication number

TWI612045B

TWI612045B TW101133590A TW101133590A TWI612045B TW I612045 B TWI612045 B TW I612045B TW 101133590 A TW101133590 A TW 101133590A TW 101133590 A TW101133590 A TW 101133590A TW I612045 B TWI612045 B TW I612045B

Authority

TW

Taiwan

Prior art keywords

plants

formula

compound

plant

methyl

Prior art date

2011-09-15

Links

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• 239000000417 fungicide Substances 0.000 title description 10
• CXVWVEAHZKABIU-UHFFFAOYSA-N piperidine;1h-pyrazole Chemical class C=1C=NNC=1.C1CCNCC1 CXVWVEAHZKABIU-UHFFFAOYSA-N 0.000 title description 2
• 239000000203 mixture Substances 0.000 claims abstract description 106
• 238000000034 method Methods 0.000 claims abstract description 70
• 241000233866 Fungi Species 0.000 claims abstract description 38
• 150000003839 salts Chemical class 0.000 claims abstract description 26
• 230000009931 harmful effect Effects 0.000 claims abstract description 20
• 239000000463 material Substances 0.000 claims abstract description 17
• 230000003032 phytopathogenic effect Effects 0.000 claims abstract description 17
• 241001465754 Metazoa Species 0.000 claims abstract description 10
• 230000001717 pathogenic effect Effects 0.000 claims abstract description 6
• 230000036541 health Effects 0.000 claims abstract description 4
• 238000003898 horticulture Methods 0.000 claims abstract description 4
• -1 4, 5- Dimethyl-2- (prop-2-yn-1-yloxy) phenyl Chemical group 0.000 claims description 479
• 150000001875 compounds Chemical class 0.000 claims description 116
• 125000001424 substituent group Chemical group 0.000 claims description 68
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 39
• 230000009261 transgenic effect Effects 0.000 claims description 31
• 229910052739 hydrogen Inorganic materials 0.000 claims description 30
• 239000001257 hydrogen Substances 0.000 claims description 27
• 229910052760 oxygen Inorganic materials 0.000 claims description 16
• 239000001301 oxygen Substances 0.000 claims description 16
• 150000002431 hydrogen Chemical class 0.000 claims description 15
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 14
• 229910052736 halogen Inorganic materials 0.000 claims description 14
• 150000002367 halogens Chemical class 0.000 claims description 12
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
• 239000004094 surface-active agent Substances 0.000 claims description 8
• 239000004606 Fillers/Extenders Substances 0.000 claims description 7
• 150000001204 N-oxides Chemical class 0.000 claims description 7
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 5
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
• 125000006766 (C2-C6) alkynyloxy group Chemical group 0.000 claims description 4
• 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims description 4
• 125000005336 allyloxy group Chemical group 0.000 claims description 4
• 125000004760 (C1-C4) alkylsulfonylamino group Chemical group 0.000 claims 1
• 125000006765 (C2-C6) haloalkenyloxy group Chemical group 0.000 claims 1
• 238000004519 manufacturing process Methods 0.000 abstract description 28
• 241000196324 Embryophyta Species 0.000 description 310
• 108090000623 proteins and genes Proteins 0.000 description 82
• 239000004480 active ingredient Substances 0.000 description 57
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
• 238000006243 chemical reaction Methods 0.000 description 44
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
• 102000004169 proteins and genes Human genes 0.000 description 39
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 32
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 31
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
• 125000000217 alkyl group Chemical group 0.000 description 30
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
• 238000009472 formulation Methods 0.000 description 27
• GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 description 26
• 239000011541 reaction mixture Substances 0.000 description 26
• 238000002360 preparation method Methods 0.000 description 25
• 239000002904 solvent Substances 0.000 description 25
• 230000000749 insecticidal effect Effects 0.000 description 22
• 239000000243 solution Substances 0.000 description 22
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
• 241000238631 Hexapoda Species 0.000 description 21
• 239000003630 growth substance Substances 0.000 description 21
• 229910052757 nitrogen Inorganic materials 0.000 description 20
• 239000002131 composite material Substances 0.000 description 19
• 125000004432 carbon atom Chemical group C* 0.000 description 18
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 18
• 238000011282 treatment Methods 0.000 description 18
• 239000002585 base Substances 0.000 description 17
• 201000010099 disease Diseases 0.000 description 17
• 235000013399 edible fruits Nutrition 0.000 description 17
• 241000894007 species Species 0.000 description 17
• 238000005481 NMR spectroscopy Methods 0.000 description 16
• 239000000460 chlorine Substances 0.000 description 16
• 229910052801 chlorine Inorganic materials 0.000 description 16
• 238000003306 harvesting Methods 0.000 description 16
• 239000004009 herbicide Substances 0.000 description 16
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
• 102000004190 Enzymes Human genes 0.000 description 15
• 108090000790 Enzymes Proteins 0.000 description 15
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
• 230000000694 effects Effects 0.000 description 15
• 230000001965 increasing effect Effects 0.000 description 15
• 125000004433 nitrogen atom Chemical group N* 0.000 description 15
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 14
• 239000002253 acid Substances 0.000 description 14
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
• 239000000126 substance Substances 0.000 description 14
• 241000219198 Brassica Species 0.000 description 13
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 13
• 240000008042 Zea mays Species 0.000 description 13
• 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 13
• 235000002017 Zea mays subsp mays Nutrition 0.000 description 13
• 235000005822 corn Nutrition 0.000 description 13
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 13
• 239000000843 powder Substances 0.000 description 13
• 230000002829 reductive effect Effects 0.000 description 13
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 12
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 12
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
• 150000001336 alkenes Chemical class 0.000 description 12
• 150000001345 alkine derivatives Chemical class 0.000 description 12
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 12
• 229910052794 bromium Inorganic materials 0.000 description 12
• 125000000753 cycloalkyl group Chemical group 0.000 description 12
• 229910052731 fluorine Inorganic materials 0.000 description 12
• 239000000047 product Substances 0.000 description 12
• 230000009466 transformation Effects 0.000 description 12
• 229920000742 Cotton Polymers 0.000 description 11
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 11
• 241000223218 Fusarium Species 0.000 description 11
• 235000010469 Glycine max Nutrition 0.000 description 11
• 244000068988 Glycine max Species 0.000 description 11
• 241000219146 Gossypium Species 0.000 description 11
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
• 125000003342 alkenyl group Chemical group 0.000 description 11
• 238000004587 chromatography analysis Methods 0.000 description 11
• 239000011737 fluorine Substances 0.000 description 11
• 238000010353 genetic engineering Methods 0.000 description 11
• 239000000543 intermediate Substances 0.000 description 11
• 239000002689 soil Substances 0.000 description 11
• 241000223221 Fusarium oxysporum Species 0.000 description 10
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
• 125000000304 alkynyl group Chemical group 0.000 description 10
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 10
• 230000015572 biosynthetic process Effects 0.000 description 10
• 125000004093 cyano group Chemical group *C#N 0.000 description 10
• 230000006378 damage Effects 0.000 description 10
• 230000002068 genetic effect Effects 0.000 description 10
• 125000001188 haloalkyl group Chemical group 0.000 description 10
• 229910052751 metal Inorganic materials 0.000 description 10
• 239000002184 metal Chemical class 0.000 description 10
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 10
• 229910052938 sodium sulfate Inorganic materials 0.000 description 10
• 235000011152 sodium sulphate Nutrition 0.000 description 10
• 238000003786 synthesis reaction Methods 0.000 description 10
• 241000894006 Bacteria Species 0.000 description 9
• 239000003153 chemical reaction reagent Substances 0.000 description 9
• 230000001276 controlling effect Effects 0.000 description 9
• 239000002270 dispersing agent Substances 0.000 description 9
• 239000000975 dye Substances 0.000 description 9
• 239000008187 granular material Substances 0.000 description 9
• 244000005700 microbiome Species 0.000 description 9
• 230000035772 mutation Effects 0.000 description 9
• 229910052717 sulfur Chemical group 0.000 description 9
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 8
• 241000223600 Alternaria Species 0.000 description 8
• JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 8
• 240000006394 Sorghum bicolor Species 0.000 description 8
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
• 239000000853 adhesive Substances 0.000 description 8
• 230000001070 adhesive effect Effects 0.000 description 8
• 125000003545 alkoxy group Chemical group 0.000 description 8
• 125000004453 alkoxycarbonyl group Chemical group 0.000 description 8
• 125000004644 alkyl sulfinyl group Chemical group 0.000 description 8
• 125000004414 alkyl thio group Chemical group 0.000 description 8
• 229910052799 carbon Inorganic materials 0.000 description 8
• 239000012141 concentrate Substances 0.000 description 8
• 235000008504 concentrate Nutrition 0.000 description 8
• 244000038559 crop plants Species 0.000 description 8
• 239000003995 emulsifying agent Substances 0.000 description 8
• 230000000855 fungicidal effect Effects 0.000 description 8
• 230000012010 growth Effects 0.000 description 8
• 125000004438 haloalkoxy group Chemical group 0.000 description 8
• 125000000623 heterocyclic group Chemical group 0.000 description 8
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 8
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 8
• 239000003112 inhibitor Substances 0.000 description 8
• 239000003921 oil Substances 0.000 description 8
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 8
• RQCNHUCCQJMSRG-UHFFFAOYSA-N tert-butyl piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCCC1 RQCNHUCCQJMSRG-UHFFFAOYSA-N 0.000 description 8
• 238000005160 1H NMR spectroscopy Methods 0.000 description 7
• GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 7
• 235000011331 Brassica Nutrition 0.000 description 7
• 101150065749 Churc1 gene Proteins 0.000 description 7
• 102100038239 Protein Churchill Human genes 0.000 description 7
• 241000233639 Pythium Species 0.000 description 7
• 241001361634 Rhizoctonia Species 0.000 description 7
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 7
• 239000000969 carrier Substances 0.000 description 7
• 239000003085 diluting agent Substances 0.000 description 7
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
• 125000000262 haloalkenyl group Chemical group 0.000 description 7
• 125000004995 haloalkylthio group Chemical group 0.000 description 7
• 125000000232 haloalkynyl group Chemical group 0.000 description 7
• 125000005347 halocycloalkyl group Chemical group 0.000 description 7
• 125000001624 naphthyl group Chemical group 0.000 description 7
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 7
• 235000019198 oils Nutrition 0.000 description 7
• 229910000027 potassium carbonate Inorganic materials 0.000 description 7
• 235000011181 potassium carbonates Nutrition 0.000 description 7
• 238000001953 recrystallisation Methods 0.000 description 7
• 229920006395 saturated elastomer Polymers 0.000 description 7
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
• 239000007787 solid Substances 0.000 description 7
• 239000007858 starting material Substances 0.000 description 7
• 239000011593 sulfur Chemical group 0.000 description 7
• 239000003053 toxin Substances 0.000 description 7
• 231100000765 toxin Toxicity 0.000 description 7
• 108700012359 toxins Proteins 0.000 description 7
• 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 description 6
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
• 241001600407 Aphis <genus> Species 0.000 description 6
• 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 6
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 6
• 101710151559 Crystal protein Proteins 0.000 description 6
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
• 208000031888 Mycoses Diseases 0.000 description 6
• 241000221300 Puccinia Species 0.000 description 6
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
• 235000021536 Sugar beet Nutrition 0.000 description 6
• 241000223259 Trichoderma Species 0.000 description 6
• 241000607479 Yersinia pestis Species 0.000 description 6
• 150000001298 alcohols Chemical class 0.000 description 6
• 150000001299 aldehydes Chemical class 0.000 description 6
• 125000004390 alkyl sulfonyl group Chemical group 0.000 description 6
• 150000001412 amines Chemical class 0.000 description 6
• 150000001413 amino acids Chemical class 0.000 description 6
• 230000008901 benefit Effects 0.000 description 6
• 238000009395 breeding Methods 0.000 description 6
• 235000013339 cereals Nutrition 0.000 description 6
• 238000004440 column chromatography Methods 0.000 description 6
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 6
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 6
• RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 description 6
• 230000035784 germination Effects 0.000 description 6
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
• 239000007788 liquid Substances 0.000 description 6
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
• 239000012074 organic phase Substances 0.000 description 6
• 150000002923 oximes Chemical class 0.000 description 6
• 244000052769 pathogen Species 0.000 description 6
• 239000002243 precursor Substances 0.000 description 6
• 230000001681 protective effect Effects 0.000 description 6
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
• 238000003860 storage Methods 0.000 description 6
• 230000009105 vegetative growth Effects 0.000 description 6
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 5
• 0 *C(CC1)(CCN1C(C[n]1nc(C(F)F)cc1C(F)F)=*)c1nc(C(Cl)=NO)c[s]1 Chemical compound *C(CC1)(CCN1C(C[n]1nc(C(F)F)cc1C(F)F)=*)c1nc(C(Cl)=NO)c[s]1 0.000 description 5
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 5
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
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• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
• 241000233622 Phytophthora infestans Species 0.000 description 5
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• 125000000000 cycloalkoxy group Chemical group 0.000 description 5
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 5
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• IXORZMNAPKEEDV-OBDJNFEBSA-N gibberellin A3 Chemical class C([C@@]1(O)C(=C)C[C@@]2(C1)[C@H]1C(O)=O)C[C@H]2[C@]2(C=C[C@@H]3O)[C@H]1[C@]3(C)C(=O)O2 IXORZMNAPKEEDV-OBDJNFEBSA-N 0.000 description 5
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• TXIOULNLSCTYNR-UHFFFAOYSA-N 2-[3,5-bis(difluoromethyl)pyrazol-1-yl]acetic acid Chemical compound OC(=O)CN1N=C(C(F)F)C=C1C(F)F TXIOULNLSCTYNR-UHFFFAOYSA-N 0.000 description 4
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 4
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• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
• 235000002637 Nicotiana tabacum Nutrition 0.000 description 4
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