KR101977920B1 - 제초 작용을 가지는 3-페닐이속사졸린 유도체 - Google Patents
제초 작용을 가지는 3-페닐이속사졸린 유도체 Download PDFInfo
- Publication number
- KR101977920B1 KR101977920B1 KR1020157010148A KR20157010148A KR101977920B1 KR 101977920 B1 KR101977920 B1 KR 101977920B1 KR 1020157010148 A KR1020157010148 A KR 1020157010148A KR 20157010148 A KR20157010148 A KR 20157010148A KR 101977920 B1 KR101977920 B1 KR 101977920B1
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- KR
- South Korea
- Prior art keywords
- methyl
- dihydro
- oxazole
- chlorine
- fluorine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 230000002363 herbicidal effect Effects 0.000 title claims description 25
- UKFPAGCSDWQXFT-UHFFFAOYSA-N 3-phenyl-4,5-dihydro-1,2-oxazole Chemical class O1CCC(C=2C=CC=CC=2)=N1 UKFPAGCSDWQXFT-UHFFFAOYSA-N 0.000 title abstract description 14
- 239000001257 hydrogen Substances 0.000 claims abstract description 65
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 65
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 63
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 33
- 239000004009 herbicide Substances 0.000 claims abstract description 26
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 24
- -1 3-phenyl isoxazoline compound Chemical class 0.000 claims description 144
- 229910052731 fluorine Inorganic materials 0.000 claims description 128
- 239000000460 chlorine Substances 0.000 claims description 118
- 229910052801 chlorine Inorganic materials 0.000 claims description 118
- 239000011737 fluorine Substances 0.000 claims description 115
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 107
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 105
- 229910052794 bromium Inorganic materials 0.000 claims description 89
- 150000001875 compounds Chemical class 0.000 claims description 89
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 76
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 76
- 239000000203 mixture Substances 0.000 claims description 75
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 43
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 34
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 claims description 33
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 28
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 24
- 230000009261 transgenic effect Effects 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 21
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 19
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 19
- 125000006536 (C1-C2)alkoxy group Chemical group 0.000 claims description 18
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 18
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 17
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 14
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 14
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 14
- 229910052740 iodine Inorganic materials 0.000 claims description 13
- 125000006766 (C2-C6) alkynyloxy group Chemical group 0.000 claims description 12
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 12
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims description 12
- 125000006508 2,6-difluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C(F)=C1[H])C([H])([H])* 0.000 claims description 11
- 125000006509 3,4-difluorobenzyl group Chemical group [H]C1=C(F)C(F)=C([H])C(=C1[H])C([H])([H])* 0.000 claims description 11
- 125000006288 3,5-difluorobenzyl group Chemical group [H]C1=C(F)C([H])=C(C([H])=C1F)C([H])([H])* 0.000 claims description 11
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 claims description 11
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 11
- SQGDXCRPJLHCDC-UHFFFAOYSA-N CC(C(C)=O)C.C(C)C(C(=O)O)C Chemical compound CC(C(C)=O)C.C(C)C(C(=O)O)C SQGDXCRPJLHCDC-UHFFFAOYSA-N 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- KPSSIOMAKSHJJG-UHFFFAOYSA-N neopentyl alcohol Chemical compound CC(C)(C)CO KPSSIOMAKSHJJG-UHFFFAOYSA-N 0.000 claims description 11
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims description 11
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 8
- 229920002554 vinyl polymer Polymers 0.000 claims description 7
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 230000008635 plant growth Effects 0.000 claims description 6
- 239000002671 adjuvant Substances 0.000 claims description 5
- 239000003974 emollient agent Substances 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 239000003630 growth substance Substances 0.000 claims description 4
- 239000002917 insecticide Substances 0.000 claims description 4
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 4
- 229910052757 nitrogen Chemical group 0.000 claims description 4
- 244000045561 useful plants Species 0.000 claims description 4
- VPYZWWRTQYPRGL-UHFFFAOYSA-N 3-phenyl-4,5-dihydro-1,2-oxazole-5-carboxamide Chemical compound O1C(C(=O)N)CC(C=2C=CC=CC=2)=N1 VPYZWWRTQYPRGL-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 230000000895 acaricidal effect Effects 0.000 claims description 3
- 239000000642 acaricide Substances 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 239000000417 fungicide Substances 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000011593 sulfur Chemical group 0.000 claims description 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
- NJVDFRPKXPULOD-UHFFFAOYSA-N 3-phenyl-4,5-dihydro-1,2-oxazole-5-carbothioamide Chemical compound O1C(C(=S)N)CC(C=2C=CC=CC=2)=N1 NJVDFRPKXPULOD-UHFFFAOYSA-N 0.000 claims description 2
- YRMLFORXOOIJDR-UHFFFAOYSA-N Dichlormid Chemical compound ClC(Cl)C(=O)N(CC=C)CC=C YRMLFORXOOIJDR-UHFFFAOYSA-N 0.000 claims description 2
- 241000238631 Hexapoda Species 0.000 claims description 2
- 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 2
- 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
- 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 2
- 230000000361 pesticidal effect Effects 0.000 claims description 2
- 244000038559 crop plants Species 0.000 claims 5
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims 3
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 3
- 239000013003 healing agent Substances 0.000 claims 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract description 4
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 description 68
- 241000196324 Embryophyta Species 0.000 description 60
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- 238000002360 preparation method Methods 0.000 description 33
- 239000004480 active ingredient Substances 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- 238000006243 chemical reaction Methods 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 20
- 239000008187 granular material Substances 0.000 description 19
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 16
- 239000000463 material Substances 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- 108090000623 proteins and genes Proteins 0.000 description 14
- 230000000694 effects Effects 0.000 description 13
- 238000009472 formulation Methods 0.000 description 13
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 239000004094 surface-active agent Substances 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 239000000543 intermediate Substances 0.000 description 11
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- 238000003786 synthesis reaction Methods 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 230000012010 growth Effects 0.000 description 10
- 239000000843 powder Substances 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000003995 emulsifying agent Substances 0.000 description 9
- 239000002689 soil Substances 0.000 description 9
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
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- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 description 6
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- HQIDHDNPSRKLFH-UHFFFAOYSA-N CC(C)OCC(C1C)ON=C1C1=CC(C#N)=CC=C1 Chemical compound CC(C)OCC(C1C)ON=C1C1=CC(C#N)=CC=C1 HQIDHDNPSRKLFH-UHFFFAOYSA-N 0.000 description 5
- AFGSMSSTNTXMJT-UHFFFAOYSA-N CCCCOCC(C1C)ON=C1C1=CC(C#N)=CC=C1 Chemical compound CCCCOCC(C1C)ON=C1C1=CC(C#N)=CC=C1 AFGSMSSTNTXMJT-UHFFFAOYSA-N 0.000 description 5
- 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 5
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- 239000001923 methylcellulose Substances 0.000 description 1
- FMXOEQQPVONPBU-UHFFFAOYSA-N methylidene(dioxido)azanium Chemical class [O-][N+]([O-])=C FMXOEQQPVONPBU-UHFFFAOYSA-N 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
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- 235000010755 mineral Nutrition 0.000 description 1
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- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- 238000010369 molecular cloning Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- SZJWOEBXPAJXAT-UHFFFAOYSA-N n-[(2,3-difluorophenyl)methylidene]hydroxylamine Chemical compound ON=CC1=CC=CC(F)=C1F SZJWOEBXPAJXAT-UHFFFAOYSA-N 0.000 description 1
- IAYMCXBREVAUIX-UHFFFAOYSA-N n-[(3-chloro-4-fluorophenyl)methylidene]hydroxylamine Chemical compound ON=CC1=CC=C(F)C(Cl)=C1 IAYMCXBREVAUIX-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 229920000847 nonoxynol Polymers 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 239000004535 oil miscible liquid Substances 0.000 description 1
- 125000002811 oleoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 230000002018 overexpression Effects 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 235000020030 perry Nutrition 0.000 description 1
- 239000003090 pesticide formulation Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 150000003017 phosphorus Chemical class 0.000 description 1
- 230000005097 photorespiration Effects 0.000 description 1
- 239000001007 phthalocyanine dye Substances 0.000 description 1
- 239000000280 phytoalexin Substances 0.000 description 1
- 150000001857 phytoalexin derivatives Chemical class 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000013612 plasmid Substances 0.000 description 1
- 229920001495 poly(sodium acrylate) polymer Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001522 polyglycol ester Polymers 0.000 description 1
- 239000002675 polymer-supported reagent Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- JAUMGJMUKKGTEL-UHFFFAOYSA-N propan-2-yl 5-cyano-3-(3,5-difluorophenyl)-4H-1,2-oxazole-5-carboxylate Chemical compound C(#N)C1(CC(=NO1)C1=CC(=CC(=C1)F)F)C(=O)OC(C)C JAUMGJMUKKGTEL-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000003531 protein hydrolysate Substances 0.000 description 1
- 229960003351 prussian blue Drugs 0.000 description 1
- 239000013225 prussian blue Substances 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000010188 recombinant method Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 108091092562 ribozyme Proteins 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([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
- 239000003352 sequestering agent Substances 0.000 description 1
- QYOJSKGCWNAKGW-HCWXCVPCSA-N shikimate-3-phosphate Chemical compound O[C@H]1CC(C(O)=O)=C[C@H](OP(O)(O)=O)[C@@H]1O QYOJSKGCWNAKGW-HCWXCVPCSA-N 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 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
- 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
- IZWPGJFSBABFGL-GMFCBQQYSA-M sodium;2-[methyl-[(z)-octadec-9-enoyl]amino]ethanesulfonate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCC(=O)N(C)CCS([O-])(=O)=O IZWPGJFSBABFGL-GMFCBQQYSA-M 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000004550 soluble concentrate Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical class NCCS(O)(=O)=O XOAAWQZATWQOTB-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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
- DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 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
- 238000012546 transfer Methods 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 230000001018 virulence Effects 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
- 239000002699 waste material Substances 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
- 239000008096 xylene Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/04—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
-
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| EP12185768.4 | 2012-09-25 | ||
| EP12185768 | 2012-09-25 | ||
| PCT/EP2013/069453 WO2014048827A1 (de) | 2012-09-25 | 2013-09-19 | Herbizid wirksame 3-phenylisoxazolinderivate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20150063445A KR20150063445A (ko) | 2015-06-09 |
| KR101977920B1 true KR101977920B1 (ko) | 2019-05-13 |
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| KR1020157010148A Active KR101977920B1 (ko) | 2012-09-25 | 2013-09-19 | 제초 작용을 가지는 3-페닐이속사졸린 유도체 |
Country Status (13)
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|---|---|
| US (1) | US9585392B2 (enExample) |
| EP (1) | EP2900645B1 (enExample) |
| JP (1) | JP6472382B2 (enExample) |
| KR (1) | KR101977920B1 (enExample) |
| CN (1) | CN104812739B (enExample) |
| BR (1) | BR112015006573B1 (enExample) |
| DK (1) | DK2900645T3 (enExample) |
| ES (1) | ES2747483T3 (enExample) |
| IL (1) | IL237685B (enExample) |
| IN (1) | IN2015DN01315A (enExample) |
| MX (1) | MX378312B (enExample) |
| TW (1) | TWI598344B (enExample) |
| WO (1) | WO2014048827A1 (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2607889T3 (es) | 2012-09-25 | 2017-04-04 | Bayer Cropscience Ag | 3-fenilisoxazolin-5-carboxamidas 5-oxi-sustituidas y 3-fenilisoxazolin-5-tioamidas 5-oxi-sustituidas con actividad herbicida y fungicida |
| BR112015006560A2 (pt) | 2012-09-25 | 2017-07-04 | Bayer Cropscience Ag | 3-heteroaril-isoxazolina-5-carboxamidas e 3-heteroaril-isoxazolina-5-tioamidas com atividade herbicida e fungicida |
| CN105753853B (zh) | 2014-12-16 | 2020-08-04 | 沈阳中化农药化工研发有限公司 | 一种含异恶唑啉的脲嘧啶类化合物及其用途 |
| CN105198824B (zh) * | 2015-10-09 | 2018-08-31 | 苏州大学 | 一种二氢异噁唑啉化合物及其制备方法和应用 |
| CN110799511B (zh) | 2017-06-13 | 2023-09-01 | 拜耳公司 | 除草活性的四氢和二氢呋喃甲酰胺的3-苯基异噁唑啉-5-甲酰胺 |
| PT3638665T (pt) | 2017-06-13 | 2021-10-19 | Bayer Cropscience Ag | 3-fenilisoxazolino-5-carboxamidas de ácidos tetrahidrofuranocarboxílicos e de ácidos dihidrofuranocarboxílicos e dos seus ésteres com eficácia herbicida |
| EP3668845B1 (de) | 2017-08-17 | 2024-06-26 | Bayer Aktiengesellschaft | Herbizid wirksame 3-phenyl-5-trifluormethylisoxazolin-5-carboxamide von cyclopentylcarbonsäuren und -estern |
| DK3743411T3 (da) | 2018-01-25 | 2023-02-13 | Bayer Ag | Herbicidt virksomt 3-phenylisoxazolin-5-carboxamider af cyclopentenylcarbonsyrederivater |
| DK3937637T3 (da) | 2019-03-12 | 2023-07-24 | Bayer Ag | Herbicidt virksomme 3-phenylisoxazolin-5-carboxamider af s-holdige cyclopentenylcarbonsyreestere |
| WO2021082901A1 (zh) * | 2019-10-29 | 2021-05-06 | 沈阳中化农药化工研发有限公司 | 一种苯基异恶唑啉类化合物及其用途 |
| BR112022020616A2 (pt) | 2020-04-14 | 2022-11-29 | Basf Se | Compostos, composição, uso de um composto e método para controlar vegetação indesejada |
| AU2021267657A1 (en) | 2020-05-05 | 2022-12-08 | Basf Se | Condensed isoxazoline derivatives and their use as herbicides |
| US20230348366A1 (en) | 2020-10-01 | 2023-11-02 | Bayer Aktiengesellschaft | Benzaldehyde oximes and method for producing same |
| EP4250928A1 (en) * | 2020-11-24 | 2023-10-04 | Syngenta Crop Protection AG | Herbicidal compounds |
| IL305673A (en) | 2021-03-09 | 2023-11-01 | Basf Se | Melonamides and their use as herbicides |
| KR20240113831A (ko) * | 2021-12-03 | 2024-07-23 | 바이엘 악티엔게젤샤프트 | 이속사졸린-5,5-비닐카르복실산 유도체의 제조 방법 |
| CN114436834A (zh) * | 2021-12-16 | 2022-05-06 | 江苏阿尔法药业股份有限公司 | 一种利用连续流微通道反应器合成瑞舒伐他汀钙中间体的方法 |
| KR20240136380A (ko) | 2022-01-14 | 2024-09-13 | 엔코 켐 인코포레이티드 | 프로토포르피리노겐 산화효소 억제제 |
Citations (1)
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| JP2001510835A (ja) * | 1997-07-23 | 2001-08-07 | ビーエーエスエフ アクチェンゲゼルシャフト | 置換３−フェニルイソオキサゾリン |
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| GB8422701D0 (en) * | 1984-09-07 | 1984-10-10 | Shell Int Research | Ether herbicides |
| GB8423252D0 (en) | 1984-09-14 | 1984-10-17 | Shell Int Research | Ether herbicides |
| JPS62103070A (ja) * | 1985-10-29 | 1987-05-13 | Mitsui Toatsu Chem Inc | イソオキサゾリン誘導体および植物生長調節剤 |
| DE3541722A1 (de) * | 1985-11-26 | 1987-05-27 | Basf Ag | Chinolinderivate und ihre verwendung zur bekaempfung von unerwuenschtem pflanzenwachstum |
| US4956006A (en) * | 1988-12-27 | 1990-09-11 | Ici Americas Inc. | Substituted 1-phenyl pyrrolidones and their use as herbicides |
| DE4026018A1 (de) * | 1990-08-17 | 1992-02-20 | Hoechst Ag | Isoxazoline oder isothiazoline enthaltende pflanzenschuetzende mittel und neue isoxazoline und isothiazoline |
| WO1995014681A1 (en) * | 1993-11-26 | 1995-06-01 | Pfizer Inc. | Isoxazoline compounds as antiinflammatory agents |
| PT730587E (pt) * | 1993-11-26 | 2000-05-31 | Pfizer | 3-aril-2-isoxazolinas como agentes anti-inflamatorios |
| US5939418A (en) | 1995-12-21 | 1999-08-17 | The Dupont Merck Pharmaceutical Company | Isoxazoline, isothiazoline and pyrazoline factor Xa inhibitors |
| BR0013251B1 (pt) * | 1999-08-10 | 2010-11-30 | derivado de isoxazolina e herbicida que contém o mesmo como ingrediente ativo. | |
| KR100594544B1 (ko) * | 2003-08-27 | 2006-06-30 | 주식회사 엘지생명과학 | 이소옥사졸린 구조를 갖는 캐스파제 저해제 |
| BRPI0413330A (pt) * | 2003-08-29 | 2006-10-10 | Ranbaxy Lab Ltd | inibidores de fosfodiesterase do tipo iv, composição farmacêutica contendo os mesmos e processo para sua preparação |
| JP2005112840A (ja) * | 2003-09-16 | 2005-04-28 | Nissan Chem Ind Ltd | 新規ピラゾールスルホニルウレア化合物および除草剤 |
| US20070259874A1 (en) | 2003-11-26 | 2007-11-08 | Palle Venkata P | Phosphodiesterase Inhibitors |
| WO2008035315A2 (en) | 2006-09-22 | 2008-03-27 | Ranbaxy Laboratories Limited | Inhibitors of phosphodiesterase type-iv |
| PL2691379T3 (pl) | 2011-03-31 | 2017-05-31 | Bayer Intellectual Property Gmbh | Skuteczne chwastobójczo i grzybobójczo 3-fenyloizoksazolino-5-karboksamidy i 3-fenyloizoksazolino-5-tioamidy |
| BR112015006560A2 (pt) | 2012-09-25 | 2017-07-04 | Bayer Cropscience Ag | 3-heteroaril-isoxazolina-5-carboxamidas e 3-heteroaril-isoxazolina-5-tioamidas com atividade herbicida e fungicida |
| ES2607889T3 (es) | 2012-09-25 | 2017-04-04 | Bayer Cropscience Ag | 3-fenilisoxazolin-5-carboxamidas 5-oxi-sustituidas y 3-fenilisoxazolin-5-tioamidas 5-oxi-sustituidas con actividad herbicida y fungicida |
-
2013
- 2013-09-19 CN CN201380061304.2A patent/CN104812739B/zh active Active
- 2013-09-19 BR BR112015006573-2A patent/BR112015006573B1/pt active IP Right Grant
- 2013-09-19 MX MX2015003538A patent/MX378312B/es unknown
- 2013-09-19 EP EP13766930.5A patent/EP2900645B1/de active Active
- 2013-09-19 WO PCT/EP2013/069453 patent/WO2014048827A1/de not_active Ceased
- 2013-09-19 IN IN1315DEN2015 patent/IN2015DN01315A/en unknown
- 2013-09-19 US US14/430,018 patent/US9585392B2/en active Active
- 2013-09-19 JP JP2015532405A patent/JP6472382B2/ja active Active
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- 2013-09-19 KR KR1020157010148A patent/KR101977920B1/ko active Active
- 2013-09-19 DK DK13766930.5T patent/DK2900645T3/da active
- 2013-09-24 TW TW102134203A patent/TWI598344B/zh active
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2015
- 2015-03-12 IL IL23768515A patent/IL237685B/en active IP Right Grant
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| JP2001510835A (ja) * | 1997-07-23 | 2001-08-07 | ビーエーエスエフ アクチェンゲゼルシャフト | 置換３−フェニルイソオキサゾリン |
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Also Published As
| Publication number | Publication date |
|---|---|
| EP2900645B1 (de) | 2019-08-21 |
| JP6472382B2 (ja) | 2019-02-20 |
| BR112015006573B1 (pt) | 2020-11-03 |
| EP2900645A1 (de) | 2015-08-05 |
| MX2015003538A (es) | 2015-10-12 |
| US9585392B2 (en) | 2017-03-07 |
| JP2015530397A (ja) | 2015-10-15 |
| CN104812739A (zh) | 2015-07-29 |
| IL237685B (en) | 2019-11-28 |
| ES2747483T3 (es) | 2020-03-10 |
| US20150245615A1 (en) | 2015-09-03 |
| MX378312B (es) | 2025-03-10 |
| IL237685A0 (en) | 2015-05-31 |
| TWI598344B (zh) | 2017-09-11 |
| IN2015DN01315A (enExample) | 2015-07-03 |
| WO2014048827A1 (de) | 2014-04-03 |
| DK2900645T3 (da) | 2019-10-14 |
| KR20150063445A (ko) | 2015-06-09 |
| CN104812739B (zh) | 2017-12-12 |
| BR112015006573A2 (pt) | 2017-07-04 |
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