DE2243685A1 - Substituierte dioxane, verfahren zu deren herstellung und diese verbindungen enthaltende herbizid wirkende zusammensetzungen - Google Patents
Substituierte dioxane, verfahren zu deren herstellung und diese verbindungen enthaltende herbizid wirkende zusammensetzungenInfo
- Publication number
- DE2243685A1 DE2243685A1 DE2243685A DE2243685A DE2243685A1 DE 2243685 A1 DE2243685 A1 DE 2243685A1 DE 2243685 A DE2243685 A DE 2243685A DE 2243685 A DE2243685 A DE 2243685A DE 2243685 A1 DE2243685 A1 DE 2243685A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- dioxane
- cis
- methyl
- ethyl
- 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.)
- Withdrawn
Links
- 239000000203 mixture Substances 0.000 title claims description 88
- 150000001875 compounds Chemical class 0.000 title claims description 48
- 230000002363 herbicidal effect Effects 0.000 title claims description 30
- 238000000034 method Methods 0.000 title claims description 18
- 238000004519 manufacturing process Methods 0.000 title description 5
- -1 hydrogen - Chemical class 0.000 claims description 66
- 239000011541 reaction mixture Substances 0.000 claims description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 15
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 13
- 239000012312 sodium hydride Substances 0.000 claims description 13
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 12
- 239000004480 active ingredient Substances 0.000 claims description 10
- 239000012876 carrier material Substances 0.000 claims description 9
- 150000002012 dioxanes Chemical class 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 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 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 125000001188 haloalkyl group Chemical group 0.000 claims description 6
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 5
- 239000002689 soil Substances 0.000 claims 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 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 3
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 229920000166 polytrimethylene carbonate Polymers 0.000 claims description 3
- 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 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N anhydrous methyl chloride Natural products ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims description 2
- 125000005127 aryl alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000005002 aryl methyl group Chemical group 0.000 claims description 2
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000004965 chloroalkyl group Chemical group 0.000 claims description 2
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 229940102396 methyl bromide Drugs 0.000 claims description 2
- 229940050176 methyl chloride Drugs 0.000 claims description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
- 230000008635 plant growth Effects 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000003003 spiro group Chemical group 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- WERXFZRGBCZSLA-UHFFFAOYSA-N 2-(methoxymethyl)-5-methyl-1,3-dioxane Chemical compound COCC1OCC(C)CO1 WERXFZRGBCZSLA-UHFFFAOYSA-N 0.000 claims 1
- NEGZOIAWCFYOBV-UHFFFAOYSA-N 5-ethyl-1,3-dioxane Chemical compound CCC1COCOC1 NEGZOIAWCFYOBV-UHFFFAOYSA-N 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
- KYYMCORGQBKYLS-UHFFFAOYSA-N FC1=C(COC2OCC(CO2)C)C=CC=C1 Chemical compound FC1=C(COC2OCC(CO2)C)C=CC=C1 KYYMCORGQBKYLS-UHFFFAOYSA-N 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 150000001728 carbonyl compounds Chemical class 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 104
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 78
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical class O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 58
- 239000000243 solution Substances 0.000 description 49
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 28
- 239000000047 product Substances 0.000 description 28
- 239000003921 oil Substances 0.000 description 27
- 235000019198 oils Nutrition 0.000 description 27
- 238000009835 boiling Methods 0.000 description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- 239000007788 liquid Substances 0.000 description 19
- 238000010992 reflux Methods 0.000 description 19
- 239000007787 solid Substances 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 238000004458 analytical method Methods 0.000 description 17
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 17
- 241000196324 Embryophyta Species 0.000 description 16
- 239000000463 material Substances 0.000 description 16
- 239000003208 petroleum Substances 0.000 description 16
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 14
- 235000019341 magnesium sulphate Nutrition 0.000 description 14
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 238000002329 infrared spectrum Methods 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 11
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 238000004821 distillation Methods 0.000 description 9
- 238000001035 drying Methods 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 238000001953 recrystallisation Methods 0.000 description 9
- UDIPIOHLDFSMLR-UHFFFAOYSA-N 2-phenylmethoxypropane-1,3-diol Chemical compound OCC(CO)OCC1=CC=CC=C1 UDIPIOHLDFSMLR-UHFFFAOYSA-N 0.000 description 8
- 239000002270 dispersing agent Substances 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 7
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 7
- 229940073608 benzyl chloride Drugs 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 239000008187 granular material Substances 0.000 description 7
- 238000011835 investigation Methods 0.000 description 7
- 229910000029 sodium carbonate Inorganic materials 0.000 description 7
- 229910052938 sodium sulfate Inorganic materials 0.000 description 7
- 235000011152 sodium sulphate Nutrition 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- 239000008096 xylene Substances 0.000 description 7
- UAESGIBOJCAHQP-UHFFFAOYSA-N 5-phenylmethoxy-1,3-dioxane Chemical compound C=1C=CC=CC=1COC1COCOC1 UAESGIBOJCAHQP-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
- 238000005481 NMR spectroscopy Methods 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
- 238000006243 chemical reaction Methods 0.000 description 6
- 229960001701 chloroform Drugs 0.000 description 6
- 235000011187 glycerol Nutrition 0.000 description 6
- 239000002002 slurry Substances 0.000 description 6
- VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical compound C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 description 5
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 5
- 235000005474 African couch grass Nutrition 0.000 description 5
- 241001520106 Eustachys Species 0.000 description 5
- 240000008042 Zea mays Species 0.000 description 5
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 239000003995 emulsifying agent Substances 0.000 description 5
- 239000012259 ether extract Substances 0.000 description 5
- 238000005755 formation reaction Methods 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 235000011181 potassium carbonates Nutrition 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
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- 238000004809 thin layer chromatography Methods 0.000 description 5
- 239000000080 wetting agent Substances 0.000 description 5
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 4
- BWKDAAFSXYPQOS-UHFFFAOYSA-N Benzaldehyde glyceryl acetal Chemical compound O1CC(O)COC1C1=CC=CC=C1 BWKDAAFSXYPQOS-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 4
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 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
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- 239000010410 layer Substances 0.000 description 4
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- 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
- 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 3
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 3
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- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
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- 238000004587 chromatography analysis Methods 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- 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 3
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- 159000000000 sodium salts Chemical class 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- QEHXDOJPVIHUDO-UHFFFAOYSA-N (2-fluorophenyl)methanol Chemical compound OCC1=CC=CC=C1F QEHXDOJPVIHUDO-UHFFFAOYSA-N 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical group C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 2
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- 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
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- QDCBEAGPHBHTKW-UHFFFAOYSA-N 2-ethyl-5-methylidene-1,3-dioxane Chemical compound CCC1OCC(=C)CO1 QDCBEAGPHBHTKW-UHFFFAOYSA-N 0.000 description 2
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- 239000012736 aqueous medium Substances 0.000 description 2
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- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-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
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- 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
- DHMAZTUTJDQFAG-UHFFFAOYSA-N 2-(chloromethyl)-1,3-dioxan-5-ol Chemical compound OC1COC(CCl)OC1 DHMAZTUTJDQFAG-UHFFFAOYSA-N 0.000 description 1
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- GEASUTBFDRNQEF-UHFFFAOYSA-N 2-(chloromethyl)-5-phenylmethoxy-1,3-dioxane Chemical compound C1OC(CCl)OCC1OCC1=CC=CC=C1 GEASUTBFDRNQEF-UHFFFAOYSA-N 0.000 description 1
- LPZOCVVDSHQFST-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-3-ethylpyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2)CC LPZOCVVDSHQFST-UHFFFAOYSA-N 0.000 description 1
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- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
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- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
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- 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
- ANVJOEMMCWRZRQ-UHFFFAOYSA-N 5-methyl-5-[(2-methylphenyl)methoxy]-1,3-dioxane Chemical compound CC1=CC=CC=C1COC1(C)COCOC1 ANVJOEMMCWRZRQ-UHFFFAOYSA-N 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
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
- 244000024671 Brassica kaber Species 0.000 description 1
- 235000014750 Brassica kaber Nutrition 0.000 description 1
- 240000006555 Chamaerops humilis Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 241000219146 Gossypium Species 0.000 description 1
- 240000008415 Lactuca sativa Species 0.000 description 1
- 235000003228 Lactuca sativa Nutrition 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 235000021536 Sugar beet Nutrition 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- 230000004308 accommodation Effects 0.000 description 1
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- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001298 alcohols 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
- 125000000129 anionic group Chemical group 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 230000009286 beneficial effect Effects 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
- HMWYOVWMMLZFDN-UHFFFAOYSA-N benzoic acid;1,3-dioxan-5-ol Chemical compound OC1COCOC1.OC(=O)C1=CC=CC=C1 HMWYOVWMMLZFDN-UHFFFAOYSA-N 0.000 description 1
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-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
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
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- 230000003197 catalytic effect Effects 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
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- 239000012230 colorless oil Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
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- 238000005520 cutting process Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 239000002274 desiccant Substances 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
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- 238000000921 elemental analysis Methods 0.000 description 1
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- 238000003379 elimination reaction Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- AXCBHWGTRNNXKG-UHFFFAOYSA-N fluorochlorane oxide Chemical compound FCl=O AXCBHWGTRNNXKG-UHFFFAOYSA-N 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 235000012028 green salad Nutrition 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000004615 ingredient Substances 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
- 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
- 239000003350 kerosene Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 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
- 239000003960 organic solvent Substances 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000010451 perlite Substances 0.000 description 1
- 235000019362 perlite Nutrition 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920000728 polyester 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
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 235000013311 vegetables Nutrition 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
- 239000003643 water by type Substances 0.000 description 1
- 210000002268 wool Anatomy 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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US18240071A | 1971-09-21 | 1971-09-21 | |
| US22490972A | 1972-02-09 | 1972-02-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2243685A1 true DE2243685A1 (de) | 1973-03-29 |
Family
ID=26878066
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2243685A Withdrawn DE2243685A1 (de) | 1971-09-21 | 1972-09-06 | Substituierte dioxane, verfahren zu deren herstellung und diese verbindungen enthaltende herbizid wirkende zusammensetzungen |
Country Status (23)
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2428694A1 (de) * | 1973-06-18 | 1975-01-09 | Shell Int Research | 2,6-dihalogenbenzylaether |
| US4035178A (en) * | 1976-08-31 | 1977-07-12 | Fmc Corporation | Herbicidal 1,3-dioxanes |
| 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 |
| US4704227A (en) * | 1984-02-18 | 1987-11-03 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Liquid crystal compounds |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IN146343B (enrdf_load_stackoverflow) * | 1976-08-31 | 1979-05-05 | Fmc Corp | |
| DE3176532D1 (de) * | 1981-12-01 | 1987-12-23 | Dow Chemical Co | 2-cyano-substituted 1,3-dioxane and dioxolane 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 OA OA54690A patent/OA04175A/xx unknown
- 1972-09-19 JP JP47093298A patent/JPS4839623A/ja active Pending
- 1972-09-19 SU SU7201829041A patent/SU584740A3/ru active
- 1972-09-19 ES ES406847A patent/ES406847A1/es not_active Expired
- 1972-09-20 NO NO3360/72A patent/NO137996C/no unknown
- 1972-09-20 CH CH1376172A patent/CH578302A5/xx not_active IP Right Cessation
- 1972-09-20 GB GB4345272A patent/GB1406849A/en not_active Expired
- 1972-09-20 BG BG7200021424A patent/BG23894A3/xx unknown
- 1972-09-20 TR TR17323A patent/TR17323A/xx unknown
- 1972-09-20 FR FR7233329A patent/FR2153344B1/fr not_active Expired
- 1972-09-20 DK DK463872AA patent/DK141367B/da unknown
- 1972-09-20 IT IT29452/72A patent/IT967673B/it active
- 1972-09-20 SE SE7212156A patent/SE398881B/xx unknown
- 1972-09-21 NL NL7212762A patent/NL7212762A/xx not_active Application Discontinuation
- 1972-09-21 RO RO7200072293A patent/RO62794A/ro unknown
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2428694A1 (de) * | 1973-06-18 | 1975-01-09 | Shell Int Research | 2,6-dihalogenbenzylaether |
| US4035178A (en) * | 1976-08-31 | 1977-07-12 | Fmc Corporation | Herbicidal 1,3-dioxanes |
| US4704227A (en) * | 1984-02-18 | 1987-11-03 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Liquid crystal compounds |
| 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2153344B1 (enrdf_load_stackoverflow) | 1977-07-29 |
| IL40277A (en) | 1977-10-31 |
| OA04175A (fr) | 1979-12-15 |
| NL7212762A (enrdf_load_stackoverflow) | 1973-03-23 |
| BE789105A (fr) | 1973-03-21 |
| DK141367B (da) | 1980-03-03 |
| IL40227A0 (en) | 1972-11-28 |
| CH578302A5 (enrdf_load_stackoverflow) | 1976-08-13 |
| SE398881B (sv) | 1978-01-23 |
| NO137996B (no) | 1978-02-27 |
| AT327604B (de) | 1976-02-10 |
| SU584740A3 (ru) | 1977-12-15 |
| CA995679A (en) | 1976-08-24 |
| TR17323A (tr) | 1975-03-24 |
| ES406847A1 (es) | 1976-01-16 |
| IE36654B1 (en) | 1977-01-19 |
| AR193292A1 (es) | 1973-04-11 |
| GB1406849A (en) | 1975-09-17 |
| BG23894A3 (en) | 1977-11-10 |
| IE36654L (en) | 1973-03-21 |
| JPS4839623A (enrdf_load_stackoverflow) | 1973-06-11 |
| DK141367C (enrdf_load_stackoverflow) | 1980-09-22 |
| AU4613272A (en) | 1974-03-07 |
| RO62794A (fr) | 1977-11-15 |
| NO137996C (no) | 1978-06-07 |
| PH10389A (en) | 1977-03-04 |
| IT967673B (it) | 1974-03-11 |
| ATA1083573A (de) | 1975-04-15 |
| FR2153344A1 (enrdf_load_stackoverflow) | 1973-05-04 |
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