NO794159L - Herbicider og plantevekstregulerende midler. - Google Patents
Herbicider og plantevekstregulerende midler.Info
- Publication number
- NO794159L NO794159L NO794159A NO794159A NO794159L NO 794159 L NO794159 L NO 794159L NO 794159 A NO794159 A NO 794159A NO 794159 A NO794159 A NO 794159A NO 794159 L NO794159 L NO 794159L
- Authority
- NO
- Norway
- Prior art keywords
- spiro
- hydrogen
- lower alkyl
- isoxazol
- preparation
- Prior art date
Links
- 239000004009 herbicide Substances 0.000 title claims description 14
- 239000005648 plant growth regulator Substances 0.000 title claims description 12
- 238000002360 preparation method Methods 0.000 claims description 40
- 238000000034 method Methods 0.000 claims description 27
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- IWTLIIZTPVRRFW-UHFFFAOYSA-N 3-methylidene-2-benzofuran-1-one Chemical compound C1=CC=C2C(=C)OC(=O)C2=C1 IWTLIIZTPVRRFW-UHFFFAOYSA-N 0.000 claims description 9
- -1 phenoxy, phenyl Chemical group 0.000 claims description 9
- 150000002825 nitriles Chemical class 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 239000012442 inert solvent Substances 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 238000011065 in-situ storage Methods 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 46
- 241000196324 Embryophyta Species 0.000 description 36
- 239000007787 solid Substances 0.000 description 33
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 238000004458 analytical method Methods 0.000 description 20
- 239000000047 product Substances 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 239000004480 active ingredient Substances 0.000 description 19
- 239000003921 oil Substances 0.000 description 19
- 150000003413 spiro compounds Chemical class 0.000 description 19
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000001953 recrystallisation Methods 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- 230000008635 plant growth Effects 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- 239000013078 crystal Substances 0.000 description 9
- 230000002363 herbicidal effect Effects 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 238000011161 development Methods 0.000 description 6
- 239000003480 eluent Substances 0.000 description 6
- 230000012010 growth Effects 0.000 description 6
- 150000002440 hydroxy compounds Chemical class 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 230000001105 regulatory effect Effects 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- 239000012230 colorless oil Substances 0.000 description 5
- 230000018109 developmental process Effects 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- 239000011343 solid material Substances 0.000 description 5
- LFCBRWNOAMIITG-UHFFFAOYSA-N 1,2-oxazol-5-yl benzoate Chemical class C=1C=CC=CC=1C(=O)OC1=CC=NO1 LFCBRWNOAMIITG-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 244000068988 Glycine max Species 0.000 description 4
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000001963 growth medium Substances 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- CHDFNIZLAAFFPX-UHFFFAOYSA-N ethoxyethane;oxolane Chemical compound CCOCC.C1CCOC1 CHDFNIZLAAFFPX-UHFFFAOYSA-N 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 125000003003 spiro group Chemical group 0.000 description 3
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 2
- MGWWOUDQBGCMFV-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazol-5-yl benzoate Chemical compound C=1C=CC=CC=1C(=O)OC1CC=NO1 MGWWOUDQBGCMFV-UHFFFAOYSA-N 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 239000004606 Fillers/Extenders Substances 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 244000062793 Sorghum vulgare Species 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000033228 biological regulation Effects 0.000 description 2
- FAMRJOUVGYTVBN-UHFFFAOYSA-N butyl 2-[3-[3-(trifluoromethyl)phenyl]-1,2-oxazol-5-yl]benzoate Chemical compound CCCCOC(=O)C1=CC=CC=C1C1=CC(C=2C=C(C=CC=2)C(F)(F)F)=NO1 FAMRJOUVGYTVBN-UHFFFAOYSA-N 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- RBBOWEDMXHTEPA-UHFFFAOYSA-N hexane;toluene Chemical compound CCCCCC.CC1=CC=CC=C1 RBBOWEDMXHTEPA-UHFFFAOYSA-N 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- OVXOTQQNCGABCO-UHFFFAOYSA-N methyl 2-[3-(2,4-dichlorophenyl)-1,2-oxazol-5-yl]benzoate Chemical compound COC(=O)C1=CC=CC=C1C1=CC(C=2C(=CC(Cl)=CC=2)Cl)=NO1 OVXOTQQNCGABCO-UHFFFAOYSA-N 0.000 description 2
- MOCMAZDHDUNIND-UHFFFAOYSA-N methyl 2-[3-(3-phenoxyphenyl)-1,2-oxazol-5-yl]benzoate Chemical compound COC(=O)C1=CC=CC=C1C1=CC(C=2C=C(OC=3C=CC=CC=3)C=CC=2)=NO1 MOCMAZDHDUNIND-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 238000009331 sowing Methods 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- SKTYPCFEBKASAF-UHFFFAOYSA-N 2-(1,2-oxazol-5-yl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C1=CC=NO1 SKTYPCFEBKASAF-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- WZGOZRXQUNICIZ-UHFFFAOYSA-N 2-[3-(2-methylphenyl)-1,2-oxazol-5-yl]benzoic acid Chemical compound CC1=CC=CC=C1C1=NOC(C=2C(=CC=CC=2)C(O)=O)=C1 WZGOZRXQUNICIZ-UHFFFAOYSA-N 0.000 description 1
- FHTOLEVRZHZJRV-UHFFFAOYSA-N 2-[3-[3-(trifluoromethyl)phenyl]-1,2-oxazol-5-yl]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C1=CC(C=2C=C(C=CC=2)C(F)(F)F)=NO1 FHTOLEVRZHZJRV-UHFFFAOYSA-N 0.000 description 1
- UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical compound C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 description 1
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 235000009051 Ambrosia paniculata var. peruviana Nutrition 0.000 description 1
- 235000003097 Artemisia absinthium Nutrition 0.000 description 1
- 240000001851 Artemisia dracunculus Species 0.000 description 1
- 235000017731 Artemisia dracunculus ssp. dracunculus Nutrition 0.000 description 1
- 235000003261 Artemisia vulgaris Nutrition 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 240000001579 Cirsium arvense Species 0.000 description 1
- 235000005918 Cirsium arvense Nutrition 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241000234653 Cyperus Species 0.000 description 1
- 235000005853 Cyperus esculentus Nutrition 0.000 description 1
- 240000001505 Cyperus odoratus Species 0.000 description 1
- 241001303487 Digitaria <clam> Species 0.000 description 1
- 240000003173 Drymaria cordata Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 240000007049 Juglans regia Species 0.000 description 1
- 235000009496 Juglans regia Nutrition 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 241000209117 Panicum Species 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- 241000533293 Sesbania emerus Species 0.000 description 1
- 240000002439 Sorghum halepense Species 0.000 description 1
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 1
- 235000021536 Sugar beet Nutrition 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 240000007591 Tilia tomentosa Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- UHZJSITXDORUGY-UHFFFAOYSA-N [(2,4-dichlorophenyl)methylideneamino] hypochlorite Chemical compound ClON=CC1=CC=C(Cl)C=C1Cl UHZJSITXDORUGY-UHFFFAOYSA-N 0.000 description 1
- VXXRYVJFNXDVNU-UHFFFAOYSA-N [(4-chlorophenyl)methylideneamino] hypochlorite Chemical compound ClON=CC1=CC=C(Cl)C=C1 VXXRYVJFNXDVNU-UHFFFAOYSA-N 0.000 description 1
- RQTYNJRMROVVQJ-UHFFFAOYSA-N [ClH]1OC=CC=C1 Chemical class [ClH]1OC=CC=C1 RQTYNJRMROVVQJ-UHFFFAOYSA-N 0.000 description 1
- PFWJWJYILJOJTM-UHFFFAOYSA-N [[3-(trifluoromethyl)phenyl]methylideneamino] hypochlorite Chemical compound FC(F)(F)C1=CC=CC(C=NOCl)=C1 PFWJWJYILJOJTM-UHFFFAOYSA-N 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N alpha-methyl toluene Natural products CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000001138 artemisia absinthium Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- NWSBNVVOFKKFNV-UHFFFAOYSA-N chloroform;oxolane Chemical compound ClC(Cl)Cl.C1CCOC1 NWSBNVVOFKKFNV-UHFFFAOYSA-N 0.000 description 1
- 229930002875 chlorophyll Natural products 0.000 description 1
- 235000019804 chlorophyll Nutrition 0.000 description 1
- ATNHDLDRLWWWCB-AENOIHSZSA-M chlorophyll a Chemical compound C1([C@@H](C(=O)OC)C(=O)C2=C3C)=C2N2C3=CC(C(CC)=C3C)=[N+]4C3=CC3=C(C=C)C(C)=C5N3[Mg-2]42[N+]2=C1[C@@H](CCC(=O)OC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)[C@H](C)C2=C5 ATNHDLDRLWWWCB-AENOIHSZSA-M 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000007799 cork Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- SGSVFQKHBZYKMN-UHFFFAOYSA-N ethyl 2-[3-(2,4-dichlorophenyl)-1,2-oxazol-5-yl]benzoate Chemical compound CCOC(=O)C1=CC=CC=C1C1=CC(C=2C(=CC(Cl)=CC=2)Cl)=NO1 SGSVFQKHBZYKMN-UHFFFAOYSA-N 0.000 description 1
- BLFVPXWXLVGLBT-UHFFFAOYSA-N ethyl 2-[3-[3-(trifluoromethyl)phenyl]-1,2-oxazol-5-yl]benzoate Chemical compound CCOC(=O)C1=CC=CC=C1C1=CC(C=2C=C(C=CC=2)C(F)(F)F)=NO1 BLFVPXWXLVGLBT-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- KWHDXJHBFYQOTK-UHFFFAOYSA-N heptane;toluene Chemical compound CCCCCCC.CC1=CC=CC=C1 KWHDXJHBFYQOTK-UHFFFAOYSA-N 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- SRFAURKKKOKYEN-UHFFFAOYSA-N methyl 2-[3-(2-methylphenyl)-1,2-oxazol-5-yl]benzoate Chemical compound COC(=O)C1=CC=CC=C1C1=CC(C=2C(=CC=CC=2)C)=NO1 SRFAURKKKOKYEN-UHFFFAOYSA-N 0.000 description 1
- DSTNOCZKTOOGOO-UHFFFAOYSA-N methyl 2-[3-(4-chlorophenyl)-1,2-oxazol-5-yl]benzoate Chemical compound COC(=O)C1=CC=CC=C1C1=CC(C=2C=CC(Cl)=CC=2)=NO1 DSTNOCZKTOOGOO-UHFFFAOYSA-N 0.000 description 1
- UEHOGDKXLCVFHH-UHFFFAOYSA-N methyl 2-[3-[3-(trifluoromethyl)phenyl]-1,2-oxazol-5-yl]benzoate Chemical compound COC(=O)C1=CC=CC=C1C1=CC(C=2C=C(C=CC=2)C(F)(F)F)=NO1 UEHOGDKXLCVFHH-UHFFFAOYSA-N 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- 230000000051 modifying effect Effects 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- GNWXVOQHLPBSSR-UHFFFAOYSA-N oxolane;toluene Chemical compound C1CCOC1.CC1=CC=CC=C1 GNWXVOQHLPBSSR-UHFFFAOYSA-N 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
- VSUGJXBXSHHPCJ-UHFFFAOYSA-N pentyl 2-[3-[3-(trifluoromethyl)phenyl]-1,2-oxazol-5-yl]benzoate Chemical compound CCCCCOC(=O)C1=CC=CC=C1C1=CC(C=2C=C(C=CC=2)C(F)(F)F)=NO1 VSUGJXBXSHHPCJ-UHFFFAOYSA-N 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000029553 photosynthesis Effects 0.000 description 1
- 238000010672 photosynthesis Methods 0.000 description 1
- 230000008121 plant development Effects 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
- 229910052939 potassium sulfate Inorganic materials 0.000 description 1
- 235000011151 potassium sulphates Nutrition 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 230000002786 root growth Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000005549 size reduction Methods 0.000 description 1
- 238000003797 solvolysis reaction Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical class C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- 238000011179 visual inspection Methods 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/10—Spiro-condensed systems
-
- 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
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/971,462 US4209629A (en) | 1978-12-20 | 1978-12-20 | 3'-(Substituted phenyl)-spiro[isobenzofuran-1(3H),5'(4'H)-isoxazol]-3-ones |
| US05/971,158 US4208510A (en) | 1978-12-20 | 1978-12-20 | Preparation of 3-aryl-isoxazol-5-yl benzoates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO794159L true NO794159L (no) | 1980-06-23 |
Family
ID=27130542
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO794159A NO794159L (no) | 1978-12-20 | 1979-12-19 | Herbicider og plantevekstregulerende midler. |
Country Status (22)
| Country | Link |
|---|---|
| EP (1) | EP0013111B1 (hu) |
| KR (2) | KR830001655B1 (hu) |
| AR (1) | AR222198A1 (hu) |
| AT (1) | ATE6371T1 (hu) |
| AU (1) | AU526839B2 (hu) |
| BR (1) | BR7908351A (hu) |
| CA (1) | CA1126735A (hu) |
| DD (2) | DD150206A5 (hu) |
| DE (1) | DE2966714D1 (hu) |
| DK (1) | DK542679A (hu) |
| EG (1) | EG14063A (hu) |
| ES (2) | ES487010A0 (hu) |
| HU (1) | HU185207B (hu) |
| IE (1) | IE48893B1 (hu) |
| IL (1) | IL58986A (hu) |
| MX (1) | MX5928E (hu) |
| NO (1) | NO794159L (hu) |
| PH (3) | PH15522A (hu) |
| PL (2) | PL122627B1 (hu) |
| RO (3) | RO78476A (hu) |
| TR (1) | TR20327A (hu) |
| YU (2) | YU311279A (hu) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| EP4092015A4 (en) * | 2020-01-16 | 2024-03-06 | Qingdao KingAgroot Chemical Compound Co., Ltd. | CONDENSED RING-SUBSTITUTED AROMATIC COMPOUND AND METHOD FOR THE PRODUCTION THEREOF, HERBICIDE COMPOSITION AND USE THEREOF |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1279643A (fr) * | 1960-01-01 | 1961-12-22 | Res Ltd | Oxydes de nitrile et procédé pour les préparer |
| US3258397A (en) * | 1965-04-13 | 1966-06-28 | Pfizer & Co C | Substituted arylnitrile oxides as anthelminthic agents |
| US4140515A (en) * | 1977-05-12 | 1979-02-20 | Monsanto Company | Aryl-3-isoxazole benzoates as plant growth regulants and herbicides |
-
1979
- 1979-12-14 MX MX798553U patent/MX5928E/es unknown
- 1979-12-17 EP EP79302918A patent/EP0013111B1/en not_active Expired
- 1979-12-17 AT AT79302918T patent/ATE6371T1/de not_active IP Right Cessation
- 1979-12-17 DE DE7979302918T patent/DE2966714D1/de not_active Expired
- 1979-12-18 ES ES487010A patent/ES487010A0/es active Granted
- 1979-12-18 IL IL58986A patent/IL58986A/xx unknown
- 1979-12-19 HU HU79MO1071A patent/HU185207B/hu unknown
- 1979-12-19 AR AR279359A patent/AR222198A1/es active
- 1979-12-19 DD DD79217862A patent/DD150206A5/de unknown
- 1979-12-19 RO RO7999609A patent/RO78476A/ro unknown
- 1979-12-19 CA CA342,267A patent/CA1126735A/en not_active Expired
- 1979-12-19 BR BR7908351A patent/BR7908351A/pt unknown
- 1979-12-19 NO NO794159A patent/NO794159L/no unknown
- 1979-12-19 PL PL1979220530A patent/PL122627B1/pl unknown
- 1979-12-19 KR KR1019790004509A patent/KR830001655B1/ko active IP Right Grant
- 1979-12-19 IE IE2477/79A patent/IE48893B1/en unknown
- 1979-12-19 AU AU54033/79A patent/AU526839B2/en not_active Ceased
- 1979-12-19 PH PH23437A patent/PH15522A/en unknown
- 1979-12-19 RO RO106965A patent/RO83746B1/ro unknown
- 1979-12-19 EG EG764/79A patent/EG14063A/xx active
- 1979-12-19 TR TR20327A patent/TR20327A/xx unknown
- 1979-12-19 PL PL1979231827A patent/PL127220B1/pl unknown
- 1979-12-19 DK DK542679A patent/DK542679A/da not_active Application Discontinuation
- 1979-12-19 RO RO106964A patent/RO83745B1/ro unknown
- 1979-12-19 DD DD79228165A patent/DD156765A5/de unknown
- 1979-12-19 YU YU03112/79A patent/YU311279A/xx unknown
-
1980
- 1980-05-30 PH PH24095A patent/PH15358A/en unknown
- 1980-07-31 ES ES493882A patent/ES8106712A1/es not_active Expired
-
1981
- 1981-11-19 PH PH26523A patent/PH16314A/en unknown
-
1983
- 1983-02-16 YU YU00368/83A patent/YU36883A/xx unknown
- 1983-05-14 KR KR1019830002148A patent/KR830001666B1/ko active
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