DK141367B - Herbicidt aktive dioxaner. - Google Patents
Herbicidt aktive dioxaner. Download PDFInfo
- Publication number
- DK141367B DK141367B DK463872AA DK463872A DK141367B DK 141367 B DK141367 B DK 141367B DK 463872A A DK463872A A DK 463872AA DK 463872 A DK463872 A DK 463872A DK 141367 B DK141367 B DK 141367B
- Authority
- DK
- Denmark
- Prior art keywords
- dioxane
- cis
- methyl
- mixture
- benzyloxy
- Prior art date
Links
- 230000002363 herbicidal effect Effects 0.000 title description 28
- 239000004009 herbicide Substances 0.000 title description 13
- 150000002012 dioxanes Chemical class 0.000 title description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 101
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 75
- 239000000203 mixture Substances 0.000 description 70
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 50
- 239000000243 solution Substances 0.000 description 39
- -1 cyclic acetal Chemical class 0.000 description 38
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 32
- 150000001875 compounds Chemical class 0.000 description 31
- 239000011541 reaction mixture Substances 0.000 description 28
- 239000000047 product Substances 0.000 description 26
- 241000196324 Embryophyta Species 0.000 description 24
- 239000003921 oil Substances 0.000 description 24
- 235000019198 oils Nutrition 0.000 description 24
- 239000007788 liquid Substances 0.000 description 22
- 238000004458 analytical method Methods 0.000 description 21
- 239000002689 soil Substances 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- 238000002360 preparation method Methods 0.000 description 19
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 18
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 16
- 235000019341 magnesium sulphate Nutrition 0.000 description 16
- 239000003208 petroleum Substances 0.000 description 16
- 239000007787 solid Substances 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 238000001228 spectrum Methods 0.000 description 14
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 14
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 13
- 239000012312 sodium hydride Substances 0.000 description 13
- 229910000104 sodium hydride Inorganic materials 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
- 230000008033 biological extinction Effects 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 238000004821 distillation Methods 0.000 description 11
- 229910052739 hydrogen Inorganic materials 0.000 description 11
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
- 239000004480 active ingredient Substances 0.000 description 10
- 125000000217 alkyl group Chemical group 0.000 description 10
- 238000001035 drying Methods 0.000 description 10
- 238000002474 experimental method Methods 0.000 description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- 239000000843 powder Substances 0.000 description 10
- 238000001953 recrystallisation Methods 0.000 description 10
- 125000001424 substituent group Chemical group 0.000 description 10
- UAESGIBOJCAHQP-UHFFFAOYSA-N 5-phenylmethoxy-1,3-dioxane Chemical compound C=1C=CC=CC=1COC1COCOC1 UAESGIBOJCAHQP-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000002270 dispersing agent Substances 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
- UDIPIOHLDFSMLR-UHFFFAOYSA-N 2-phenylmethoxypropane-1,3-diol Chemical compound OCC(CO)OCC1=CC=CC=C1 UDIPIOHLDFSMLR-UHFFFAOYSA-N 0.000 description 7
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 7
- 230000008020 evaporation Effects 0.000 description 7
- 239000002002 slurry Substances 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- 229910052938 sodium sulfate Inorganic materials 0.000 description 7
- 235000011152 sodium sulphate Nutrition 0.000 description 7
- 239000008096 xylene Substances 0.000 description 7
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 6
- 244000237956 Amaranthus retroflexus Species 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 6
- 229940073608 benzyl chloride Drugs 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 239000005416 organic matter Substances 0.000 description 6
- WZKXQJURGRERJY-UHFFFAOYSA-N 2-[(2-fluorophenyl)methoxy]-2-methylpropane-1,3-diol Chemical compound OCC(C)(CO)OCC1=CC=CC=C1F WZKXQJURGRERJY-UHFFFAOYSA-N 0.000 description 5
- 229920000742 Cotton Polymers 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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 5
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- RPZCVZVTXRZDAZ-UHFFFAOYSA-N diethyl 2-[(2-fluorophenyl)methoxy]-2-methylpropanedioate Chemical compound CCOC(=O)C(C)(C(=O)OCC)OCC1=CC=CC=C1F RPZCVZVTXRZDAZ-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000004495 emulsifiable concentrate Substances 0.000 description 5
- 239000003995 emulsifying agent Substances 0.000 description 5
- 239000012259 ether extract Substances 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 235000011181 potassium carbonates Nutrition 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000012265 solid product Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000003053 toxin Substances 0.000 description 5
- 231100000765 toxin Toxicity 0.000 description 5
- 239000000080 wetting agent Substances 0.000 description 5
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 4
- VCKSNYNNVSOWEE-UHFFFAOYSA-N 1,3-dioxan-5-ol Chemical compound OC1COCOC1 VCKSNYNNVSOWEE-UHFFFAOYSA-N 0.000 description 4
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 4
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 4
- 244000036975 Ambrosia artemisiifolia Species 0.000 description 4
- 235000003133 Ambrosia artemisiifolia Nutrition 0.000 description 4
- 240000006122 Chenopodium album Species 0.000 description 4
- 235000009344 Chenopodium album Nutrition 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 240000008042 Zea mays Species 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 150000004862 dioxolanes Chemical class 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- 238000009736 wetting Methods 0.000 description 4
- RNQWXOKSUCPOFS-UHFFFAOYSA-N 1,4-dioxan-2-ol Chemical compound OC1COCCO1 RNQWXOKSUCPOFS-UHFFFAOYSA-N 0.000 description 3
- XCARXOGXWMRQIN-UHFFFAOYSA-N 2-(3-fluorophenyl)-1,3-dioxan-5-ol Chemical compound O1CC(O)COC1C1=CC=CC(F)=C1 XCARXOGXWMRQIN-UHFFFAOYSA-N 0.000 description 3
- GEASUTBFDRNQEF-UHFFFAOYSA-N 2-(chloromethyl)-5-phenylmethoxy-1,3-dioxane Chemical compound C1OC(CCl)OCC1OCC1=CC=CC=C1 GEASUTBFDRNQEF-UHFFFAOYSA-N 0.000 description 3
- UJBZRWXLUJWIEB-UHFFFAOYSA-N 2-(furan-2-yl)-5-phenylmethoxy-1,3-dioxane Chemical compound C=1C=CC=CC=1COC(CO1)COC1C1=CC=CO1 UJBZRWXLUJWIEB-UHFFFAOYSA-N 0.000 description 3
- JASINQNJRVUSBZ-UHFFFAOYSA-N 2-methyl-5-phenylmethoxy-1,3-dioxane Chemical compound C1OC(C)OCC1OCC1=CC=CC=C1 JASINQNJRVUSBZ-UHFFFAOYSA-N 0.000 description 3
- BWKDAAFSXYPQOS-UHFFFAOYSA-N Benzaldehyde glyceryl acetal Chemical compound O1CC(O)COC1C1=CC=CC=C1 BWKDAAFSXYPQOS-UHFFFAOYSA-N 0.000 description 3
- 244000152970 Digitaria sanguinalis Species 0.000 description 3
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 3
- 235000010469 Glycine max Nutrition 0.000 description 3
- 244000068988 Glycine max Species 0.000 description 3
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 3
- 244000046052 Phaseolus vulgaris Species 0.000 description 3
- 235000017016 Setaria faberi Nutrition 0.000 description 3
- 241001355178 Setaria faberi Species 0.000 description 3
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
- 238000006359 acetalization reaction Methods 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 3
- 235000005822 corn Nutrition 0.000 description 3
- 238000006266 etherification reaction Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 125000002541 furyl group Chemical group 0.000 description 3
- 125000001188 haloalkyl group Chemical group 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 238000012216 screening Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- QEHXDOJPVIHUDO-UHFFFAOYSA-N (2-fluorophenyl)methanol Chemical compound OCC1=CC=CC=C1F QEHXDOJPVIHUDO-UHFFFAOYSA-N 0.000 description 2
- IHWUPMSVNMUIJX-UHFFFAOYSA-N (2-methyl-1,3-dioxan-5-yl) benzoate Chemical compound C1OC(C)OCC1OC(=O)C1=CC=CC=C1 IHWUPMSVNMUIJX-UHFFFAOYSA-N 0.000 description 2
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 2
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical group C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 229940035437 1,3-propanediol Drugs 0.000 description 2
- WGVYCXYGPNNUQA-UHFFFAOYSA-N 1-(bromomethyl)-2-methylbenzene Chemical compound CC1=CC=CC=C1CBr WGVYCXYGPNNUQA-UHFFFAOYSA-N 0.000 description 2
- MOBRMRJUKNQBMY-UHFFFAOYSA-N 1-(chloromethyl)-2-fluorobenzene Chemical compound FC1=CC=CC=C1CCl MOBRMRJUKNQBMY-UHFFFAOYSA-N 0.000 description 2
- GRCLCWDBGAEPIN-UHFFFAOYSA-N 2-(3-fluorophenyl)-5-phenylmethoxy-1,3-dioxane Chemical compound FC1=CC=CC(C2OCC(CO2)OCC=2C=CC=CC=2)=C1 GRCLCWDBGAEPIN-UHFFFAOYSA-N 0.000 description 2
- DHMAZTUTJDQFAG-UHFFFAOYSA-N 2-(chloromethyl)-1,3-dioxan-5-ol Chemical compound OC1COC(CCl)OC1 DHMAZTUTJDQFAG-UHFFFAOYSA-N 0.000 description 2
- YBRIUPLTKFBNNE-UHFFFAOYSA-N 2-(chloromethyl)-5-[(2-methylphenyl)methoxy]-1,3-dioxane Chemical compound CC1=CC=CC=C1COC1COC(CCl)OC1 YBRIUPLTKFBNNE-UHFFFAOYSA-N 0.000 description 2
- KIWWJRDYPRHMNL-UHFFFAOYSA-N 2-ethyl-5-methyl-1,3-dioxan-5-ol Chemical compound CCC1OCC(C)(O)CO1 KIWWJRDYPRHMNL-UHFFFAOYSA-N 0.000 description 2
- LYULANJSVNVULZ-UHFFFAOYSA-N 2-phenyl-5-phenylmethoxy-1,3-dioxane Chemical compound C=1C=CC=CC=1COC(CO1)COC1C1=CC=CC=C1 LYULANJSVNVULZ-UHFFFAOYSA-N 0.000 description 2
- GMCAGELUBLAWJK-UHFFFAOYSA-N 5-[(2-fluorophenyl)methoxy]-2-phenyl-1,3-dioxane Chemical compound FC1=CC=CC=C1COC1COC(C=2C=CC=CC=2)OC1 GMCAGELUBLAWJK-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- 244000105624 Arachis hypogaea Species 0.000 description 2
- 244000056139 Brassica cretica Species 0.000 description 2
- 235000003351 Brassica cretica Nutrition 0.000 description 2
- 235000003343 Brassica rupestris Nutrition 0.000 description 2
- 244000045232 Canavalia ensiformis Species 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- HSSBORCLYSCBJR-UHFFFAOYSA-N Chloramben Chemical compound NC1=CC(Cl)=CC(C(O)=O)=C1Cl HSSBORCLYSCBJR-UHFFFAOYSA-N 0.000 description 2
- 244000000626 Daucus carota Species 0.000 description 2
- 235000002767 Daucus carota Nutrition 0.000 description 2
- 244000058871 Echinochloa crus-galli Species 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 240000008415 Lactuca sativa Species 0.000 description 2
- 235000003228 Lactuca sativa Nutrition 0.000 description 2
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
- 235000011999 Panicum crusgalli Nutrition 0.000 description 2
- 235000010617 Phaseolus lunatus Nutrition 0.000 description 2
- 241000209504 Poaceae Species 0.000 description 2
- 241000219053 Rumex Species 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 240000003768 Solanum lycopersicum Species 0.000 description 2
- 101150052863 THY1 gene Proteins 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 2
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 125000004966 cyanoalkyl group Chemical group 0.000 description 2
- 239000002274 desiccant Substances 0.000 description 2
- CSLQAXTUGPUBCW-UHFFFAOYSA-N diethyl 2-bromo-2-methylpropanedioate Chemical compound CCOC(=O)C(C)(Br)C(=O)OCC CSLQAXTUGPUBCW-UHFFFAOYSA-N 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 150000002118 epoxides Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- 238000007429 general method Methods 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 235000010460 mustard Nutrition 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
- 235000020232 peanut Nutrition 0.000 description 2
- 230000008635 plant growth Effects 0.000 description 2
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- 239000010802 sludge Substances 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 238000009331 sowing Methods 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 238000004611 spectroscopical analysis Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000012258 stirred mixture Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 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
- 125000001544 thienyl group Chemical group 0.000 description 2
- RYVBINGWVJJDPU-UHFFFAOYSA-M tributyl(hexadecyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC RYVBINGWVJJDPU-UHFFFAOYSA-M 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 1
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 1
- PCYADPMXIILFTP-UHFFFAOYSA-N 1,1-diethoxy-2-methoxyethane Chemical compound CCOC(COC)OCC PCYADPMXIILFTP-UHFFFAOYSA-N 0.000 description 1
- AMLMBWVCZUMIPW-UHFFFAOYSA-N 1,3-dioxan-2-yl benzoate Chemical compound C=1C=CC=CC=1C(=O)OC1OCCCO1 AMLMBWVCZUMIPW-UHFFFAOYSA-N 0.000 description 1
- 150000000093 1,3-dioxanes Chemical class 0.000 description 1
- BOHGAOWOIJMTPZ-UHFFFAOYSA-N 1,3-dioxolan-4-ylmethanol Chemical class OCC1COCO1 BOHGAOWOIJMTPZ-UHFFFAOYSA-N 0.000 description 1
- VQRBXYBBGHOGFT-UHFFFAOYSA-N 1-(chloromethyl)-2-methylbenzene Chemical compound CC1=CC=CC=C1CCl VQRBXYBBGHOGFT-UHFFFAOYSA-N 0.000 description 1
- DMHZDOTYAVHSEH-UHFFFAOYSA-N 1-(chloromethyl)-4-methylbenzene Chemical compound CC1=CC=C(CCl)C=C1 DMHZDOTYAVHSEH-UHFFFAOYSA-N 0.000 description 1
- OMTBMVJQYXLWAE-UHFFFAOYSA-N 2,5-diethyl-5-[(2-fluorophenyl)methoxy]-1,3-dioxane Chemical compound C1OC(CC)OCC1(CC)OCC1=CC=CC=C1F OMTBMVJQYXLWAE-UHFFFAOYSA-N 0.000 description 1
- WXKWKNVAWSDNLG-UHFFFAOYSA-N 2-(2-ethoxyphenyl)-5-phenylmethoxy-1,3-dioxane Chemical compound CCOC1=CC=CC=C1C1OCC(OCC=2C=CC=CC=2)CO1 WXKWKNVAWSDNLG-UHFFFAOYSA-N 0.000 description 1
- KLTWCFMCDLEURG-UHFFFAOYSA-N 2-(2-fluorophenyl)-5-phenylmethoxy-1,3-dioxane Chemical compound FC1=CC=CC=C1C1OCC(OCC=2C=CC=CC=2)CO1 KLTWCFMCDLEURG-UHFFFAOYSA-N 0.000 description 1
- CZUFFZBAOIPGKQ-UHFFFAOYSA-N 2-(2-methoxyphenyl)-5-phenylmethoxy-1,3-dioxane Chemical compound COC1=CC=CC=C1C1OCC(OCC=2C=CC=CC=2)CO1 CZUFFZBAOIPGKQ-UHFFFAOYSA-N 0.000 description 1
- ZVIKDNXISFOMPU-UHFFFAOYSA-N 2-(3-fluorophenyl)-5-[(2-fluorophenyl)methoxy]-1,3-dioxane Chemical compound FC1=CC=CC(C2OCC(CO2)OCC=2C(=CC=CC=2)F)=C1 ZVIKDNXISFOMPU-UHFFFAOYSA-N 0.000 description 1
- KSLZVZCFDYNZQK-UHFFFAOYSA-N 2-(3-methoxyphenyl)-5-phenylmethoxy-1,3-dioxane Chemical compound COC1=CC=CC(C2OCC(CO2)OCC=2C=CC=CC=2)=C1 KSLZVZCFDYNZQK-UHFFFAOYSA-N 0.000 description 1
- BWYHAHQMECAMAR-UHFFFAOYSA-N 2-(bromomethyl)-5-phenylmethoxy-1,3-dioxane Chemical compound C1OC(CBr)OCC1OCC1=CC=CC=C1 BWYHAHQMECAMAR-UHFFFAOYSA-N 0.000 description 1
- NUHDKJAUAXCWED-UHFFFAOYSA-N 2-(chloromethyl)-5-[(2-fluorophenyl)methoxy]-5-methyl-1,3-dioxane Chemical compound C=1C=CC=C(F)C=1COC1(C)COC(CCl)OC1 NUHDKJAUAXCWED-UHFFFAOYSA-N 0.000 description 1
- HDNRCMSNNPLGFO-UHFFFAOYSA-N 2-(furan-2-yl)-5-[(2-methylphenyl)methoxy]-1,3-dioxane Chemical compound CC1=CC=CC=C1COC1COC(C=2OC=CC=2)OC1 HDNRCMSNNPLGFO-UHFFFAOYSA-N 0.000 description 1
- YOZVYJSSXPBWRF-UHFFFAOYSA-N 2-[(3-chlorophenoxy)methyl]-5-phenylmethoxy-1,3-dioxane Chemical compound ClC1=CC=CC(OCC2OCC(CO2)OCC=2C=CC=CC=2)=C1 YOZVYJSSXPBWRF-UHFFFAOYSA-N 0.000 description 1
- YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 description 1
- OVXJWSYBABKZMD-UHFFFAOYSA-N 2-chloro-1,1-diethoxyethane Chemical compound CCOC(CCl)OCC OVXJWSYBABKZMD-UHFFFAOYSA-N 0.000 description 1
- CRZJPEIBPQWDGJ-UHFFFAOYSA-N 2-chloro-1,1-dimethoxyethane Chemical compound COC(CCl)OC CRZJPEIBPQWDGJ-UHFFFAOYSA-N 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- GLEDFKMOWGWMGL-UHFFFAOYSA-N 2-ethyl-2-[(2-fluorophenyl)methoxy]propane-1,3-diol Chemical compound CCC(CO)(CO)OCC1=CC=CC=C1F GLEDFKMOWGWMGL-UHFFFAOYSA-N 0.000 description 1
- WLSBXUTYJZHJDW-UHFFFAOYSA-N 2-ethyl-5-[(2-fluorophenyl)methoxy]-5-methyl-1,3-dioxane Chemical compound C1OC(CC)OCC1(C)OCC1=CC=CC=C1F WLSBXUTYJZHJDW-UHFFFAOYSA-N 0.000 description 1
- MROZEXUYEGHFEP-UHFFFAOYSA-N 2-ethyl-5-methyl-5-[(2-methylphenyl)methoxy]-1,3-dioxane Chemical compound C1OC(CC)OCC1(C)OCC1=CC=CC=C1C MROZEXUYEGHFEP-UHFFFAOYSA-N 0.000 description 1
- QDCBEAGPHBHTKW-UHFFFAOYSA-N 2-ethyl-5-methylidene-1,3-dioxane Chemical compound CCC1OCC(=C)CO1 QDCBEAGPHBHTKW-UHFFFAOYSA-N 0.000 description 1
- RLVMGTURHNLOJX-UHFFFAOYSA-N 2-methyl-1,3-dioxan-5-ol Chemical compound CC1OCC(O)CO1 RLVMGTURHNLOJX-UHFFFAOYSA-N 0.000 description 1
- JFFYKITVXPZLQS-UHFFFAOYSA-N 2-methylidenepropane-1,3-diol Chemical compound OCC(=C)CO JFFYKITVXPZLQS-UHFFFAOYSA-N 0.000 description 1
- PFJQPZMTKVAIGA-UHFFFAOYSA-N 2-phenyl-5-[(2,3,6-trichlorophenyl)methoxy]-1,3-dioxane Chemical compound ClC1=CC=C(Cl)C(COC2COC(OC2)C=2C=CC=CC=2)=C1Cl PFJQPZMTKVAIGA-UHFFFAOYSA-N 0.000 description 1
- QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 description 1
- PIKNVEVCWAAOMJ-UHFFFAOYSA-N 3-fluorobenzaldehyde Chemical compound FC1=CC=CC(C=O)=C1 PIKNVEVCWAAOMJ-UHFFFAOYSA-N 0.000 description 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 1
- MPSCZEFPEBUTHJ-UHFFFAOYSA-N 4-[(2-phenyl-1,3-dioxan-5-yl)oxymethyl]benzonitrile Chemical compound C1=CC(C#N)=CC=C1COC1COC(C=2C=CC=CC=2)OC1 MPSCZEFPEBUTHJ-UHFFFAOYSA-N 0.000 description 1
- ZNTXHVJPXKUFOK-UHFFFAOYSA-N 5-[(2-fluorophenyl)methoxy]-2-(furan-2-yl)-1,3-dioxane Chemical compound FC1=CC=CC=C1COC1COC(C=2OC=CC=2)OC1 ZNTXHVJPXKUFOK-UHFFFAOYSA-N 0.000 description 1
- KQFIJZCTDRSHMX-UHFFFAOYSA-N 5-[(3-methylphenyl)methoxy]-2-phenyl-1,3-dioxane Chemical compound CC1=CC=CC(COC2COC(OC2)C=2C=CC=CC=2)=C1 KQFIJZCTDRSHMX-UHFFFAOYSA-N 0.000 description 1
- MYZZCFNNGCBOAS-UHFFFAOYSA-N 5-[(4-methylphenyl)methoxy]-2-phenyl-1,3-dioxane Chemical compound C1=CC(C)=CC=C1COC1COC(C=2C=CC=CC=2)OC1 MYZZCFNNGCBOAS-UHFFFAOYSA-N 0.000 description 1
- RLSCVQIAWTXAQS-UHFFFAOYSA-N 5-phenylmethoxy-2-(3-phenylmethoxyphenyl)-1,3-dioxane Chemical compound C=1C=CC=CC=1COC(CO1)COC1C(C=1)=CC=CC=1OCC1=CC=CC=C1 RLSCVQIAWTXAQS-UHFFFAOYSA-N 0.000 description 1
- KIYFILZSGCWDGD-UHFFFAOYSA-N 5-phenylmethoxy-2-(phenylmethoxymethyl)-1,3-dioxane Chemical compound O1CC(OCC=2C=CC=CC=2)COC1COCC1=CC=CC=C1 KIYFILZSGCWDGD-UHFFFAOYSA-N 0.000 description 1
- 241000219144 Abutilon Species 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 235000017060 Arachis glabrata Nutrition 0.000 description 1
- 235000010777 Arachis hypogaea Nutrition 0.000 description 1
- 235000018262 Arachis monticola Nutrition 0.000 description 1
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
- 235000014750 Brassica kaber Nutrition 0.000 description 1
- 244000024671 Brassica kaber Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 235000000509 Chenopodium ambrosioides Nutrition 0.000 description 1
- 244000098897 Chenopodium botrys Species 0.000 description 1
- 235000005490 Chenopodium botrys Nutrition 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 241001057636 Dracaena deremensis Species 0.000 description 1
- 241000508725 Elymus repens Species 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 241000219146 Gossypium Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 241001148659 Panicum dichotomiflorum Species 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- 241000205407 Polygonum Species 0.000 description 1
- 241000219295 Portulaca Species 0.000 description 1
- 235000001855 Portulaca oleracea Nutrition 0.000 description 1
- 244000234609 Portulaca oleracea Species 0.000 description 1
- 235000008515 Setaria glauca Nutrition 0.000 description 1
- 244000010062 Setaria pumila Species 0.000 description 1
- 235000021536 Sugar beet Nutrition 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 241000219793 Trifolium Species 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- 241000482268 Zea mays subsp. mays Species 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229920003232 aliphatic polyester Polymers 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical class 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- NEHMKBQYUWJMIP-UHFFFAOYSA-N anhydrous methyl chloride Natural products ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 125000005002 aryl methyl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- KGNDCEVUMONOKF-UGPLYTSKSA-N benzyl n-[(2r)-1-[(2s,4r)-2-[[(2s)-6-amino-1-(1,3-benzoxazol-2-yl)-1,1-dihydroxyhexan-2-yl]carbamoyl]-4-[(4-methylphenyl)methoxy]pyrrolidin-1-yl]-1-oxo-4-phenylbutan-2-yl]carbamate Chemical compound C1=CC(C)=CC=C1CO[C@H]1CN(C(=O)[C@@H](CCC=2C=CC=CC=2)NC(=O)OCC=2C=CC=CC=2)[C@H](C(=O)N[C@@H](CCCCN)C(O)(O)C=2OC3=CC=CC=C3N=2)C1 KGNDCEVUMONOKF-UGPLYTSKSA-N 0.000 description 1
- 125000006515 benzyloxy alkyl group Chemical class 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 125000004965 chloroalkyl group Chemical group 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000011362 coarse particle Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229940126208 compound 22 Drugs 0.000 description 1
- 229940125833 compound 23 Drugs 0.000 description 1
- 229940125846 compound 25 Drugs 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 244000038559 crop plants Species 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000012156 elution solvent Substances 0.000 description 1
- 230000008029 eradication Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 229910003480 inorganic solid Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 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
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 239000010451 perlite Substances 0.000 description 1
- 235000019362 perlite Nutrition 0.000 description 1
- 125000005359 phenoxyalkyl group Chemical class 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000003822 preparative gas chromatography Methods 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- JBYXPOFIGCOSSB-UQGDGPGGSA-N rumenic acid Chemical compound CCCCCC\C=C/C=C/CCCCCCCC(O)=O JBYXPOFIGCOSSB-UQGDGPGGSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(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
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/08—1,3-Dioxanes; Hydrogenated 1,3-dioxanes condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/14—Unsaturated ethers
- C07C43/178—Unsaturated ethers containing hydroxy or O-metal groups
- C07C43/1782—Unsaturated ethers containing hydroxy or O-metal groups containing six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK214176A DK214176A (da) | 1971-09-21 | 1976-05-13 | Fremgangsmade til bekempelse af uonsket plantevekst samt herbicid til anvendelse ved fremgangsmaden |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US18240071A | 1971-09-21 | 1971-09-21 | |
| US18240071 | 1971-09-21 | ||
| US22490972A | 1972-02-09 | 1972-02-09 | |
| US22490972 | 1972-02-09 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DK141367B true DK141367B (da) | 1980-03-03 |
| DK141367C DK141367C (enrdf_load_stackoverflow) | 1980-09-22 |
Family
ID=26878066
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK463872AA DK141367B (da) | 1971-09-21 | 1972-09-20 | Herbicidt aktive dioxaner. |
Country Status (23)
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1470509A (en) * | 1973-06-18 | 1977-04-14 | Shell Int Research | Dihalobenzyl ethers |
| US4035178A (en) * | 1976-08-31 | 1977-07-12 | Fmc Corporation | Herbicidal 1,3-dioxanes |
| IN146343B (enrdf_load_stackoverflow) * | 1976-08-31 | 1979-05-05 | Fmc Corp | |
| EP0080529B1 (en) * | 1981-12-01 | 1987-11-19 | The Dow Chemical Company | 2-cyano-substituted 1,3-dioxane and dioxolane derivatives |
| DE3405914A1 (de) * | 1984-02-18 | 1985-08-22 | Merck Patent Gmbh, 6100 Darmstadt | Fluessigkristalline verbindungen |
| US4554011A (en) * | 1984-08-24 | 1985-11-19 | Chevron Research Company | Herbicidal 2S-(2β,4β,5β)-5-Arylmethoxy-4-substituted 2-alkyl-1,3-dioxane derivatives |
| DE10301110A1 (de) * | 2003-01-09 | 2004-07-22 | Bayer Cropscience Gmbh | Substituierte Benzoylderivate als Herbizide |
-
0
- BE BE789105D patent/BE789105A/xx unknown
-
1972
- 1972-08-22 CA CA149,950A patent/CA995679A/en not_active Expired
- 1972-08-24 IE IE1161/72A patent/IE36654B1/xx unknown
- 1972-08-29 IL IL40277A patent/IL40277A/xx unknown
- 1972-08-29 IL IL40227A patent/IL40227A0/xx unknown
- 1972-09-04 PH PH13863A patent/PH10389A/en unknown
- 1972-09-06 DE DE2243685A patent/DE2243685A1/de not_active Withdrawn
- 1972-09-14 AT AT1083573*7A patent/AT327604B/de not_active IP Right Cessation
- 1972-09-15 AR AR244107A patent/AR193292A1/es active
- 1972-09-19 ES ES406847A patent/ES406847A1/es not_active Expired
- 1972-09-19 SU SU7201829041A patent/SU584740A3/ru active
- 1972-09-19 OA OA54690A patent/OA04175A/xx unknown
- 1972-09-19 JP JP47093298A patent/JPS4839623A/ja active Pending
- 1972-09-20 CH CH1376172A patent/CH578302A5/xx not_active IP Right Cessation
- 1972-09-20 SE SE7212156A patent/SE398881B/xx unknown
- 1972-09-20 TR TR17323A patent/TR17323A/xx unknown
- 1972-09-20 DK DK463872AA patent/DK141367B/da unknown
- 1972-09-20 FR FR7233329A patent/FR2153344B1/fr not_active Expired
- 1972-09-20 GB GB4345272A patent/GB1406849A/en not_active Expired
- 1972-09-20 IT IT29452/72A patent/IT967673B/it active
- 1972-09-20 BG BG7200021424A patent/BG23894A3/xx unknown
- 1972-09-20 NO NO3360/72A patent/NO137996C/no unknown
- 1972-09-21 RO RO7200072293A patent/RO62794A/ro unknown
- 1972-09-21 NL NL7212762A patent/NL7212762A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| NO137996B (no) | 1978-02-27 |
| AU4613272A (en) | 1974-03-07 |
| CH578302A5 (enrdf_load_stackoverflow) | 1976-08-13 |
| FR2153344B1 (enrdf_load_stackoverflow) | 1977-07-29 |
| SU584740A3 (ru) | 1977-12-15 |
| JPS4839623A (enrdf_load_stackoverflow) | 1973-06-11 |
| DE2243685A1 (de) | 1973-03-29 |
| IE36654L (en) | 1973-03-21 |
| RO62794A (fr) | 1977-11-15 |
| ATA1083573A (de) | 1975-04-15 |
| PH10389A (en) | 1977-03-04 |
| CA995679A (en) | 1976-08-24 |
| DK141367C (enrdf_load_stackoverflow) | 1980-09-22 |
| IT967673B (it) | 1974-03-11 |
| SE398881B (sv) | 1978-01-23 |
| BG23894A3 (en) | 1977-11-10 |
| NL7212762A (enrdf_load_stackoverflow) | 1973-03-23 |
| IL40277A (en) | 1977-10-31 |
| AT327604B (de) | 1976-02-10 |
| FR2153344A1 (enrdf_load_stackoverflow) | 1973-05-04 |
| IE36654B1 (en) | 1977-01-19 |
| NO137996C (no) | 1978-06-07 |
| TR17323A (tr) | 1975-03-24 |
| IL40227A0 (en) | 1972-11-28 |
| GB1406849A (en) | 1975-09-17 |
| OA04175A (fr) | 1979-12-15 |
| BE789105A (fr) | 1973-03-21 |
| AR193292A1 (es) | 1973-04-11 |
| ES406847A1 (es) | 1976-01-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| BG61516B2 (bg) | Пропинилов естер на 2-/4-(5-хлоро-3-флуоропиридин-2-илокси) фенокси/-пропионовата киселина и приложението й | |
| US4097581A (en) | Dioxolane derivatives | |
| US4300944A (en) | Herbicidally active unsaturated esters of halogenated α-[4-(pyridyl-2'-oxy)-phenoxy]-propionic acids | |
| US4175947A (en) | Phenoxy-phenoxypropionic acid esters | |
| US5567670A (en) | Herbicides for citrus oil palm rubber and other plantation crops | |
| JPS6126780B2 (enrdf_load_stackoverflow) | ||
| EP0288275B1 (en) | Phenoxypropionic acid derivatives for use as herbicides | |
| DK141367B (da) | Herbicidt aktive dioxaner. | |
| CA2043376A1 (en) | Sulfonylureas | |
| HU188576B (en) | Herbicides containing cyclohexane-1,3-dione-derivatives and process for the production of cyclohexane-1,3-dione-derivatives | |
| AU616983B2 (en) | Herbicidal compounds and compositions containing them | |
| US4302238A (en) | Herbicidal isoxazolidine-3,5-diones | |
| US4410354A (en) | Spiro ether herbicides | |
| CA1080236A (en) | Dioxolane derivatives | |
| US4629492A (en) | Substituted oxirane compounds | |
| US4035178A (en) | Herbicidal 1,3-dioxanes | |
| US5207818A (en) | Herbicidally active benzoxazines | |
| US4537623A (en) | Herbicidal 2-(oxa or thia heterocycle)5-amino-3-oxo-4-(substituted-phenyl)-2,3-dihydrofurans | |
| CH656133A5 (de) | Herbizid wirksame derivate von 5-desoxy-3-0-arylmethyl- oder substituierten arylmethyl-1,2,0-alkyl-idene-alpha-d-xylofuranosen. | |
| IE45464B1 (en) | Herbicidal 1,3-dioxanes | |
| US4439225A (en) | Herbicidal cyano-tetrahydrofuranylmethyl ether and cyano-tetrahydropyranylmethyl ether derivatives | |
| US4388104A (en) | 3-Phenylmethoxytetrahydropyran herbicides | |
| US4548641A (en) | Herbicides: N,N-dialkyl-2-(4-substituted-1-naphthoxy) propionamides | |
| US4978386A (en) | Herbicidal 2-(substituted-phenyl)-3-amino-2-cyclopentenone derivatives | |
| US4561876A (en) | Haloalkylcarbonylamino-1,3-dioxane herbicide antidotes |