CA1101424A - Herbicidal 1,3-dioxanes - Google Patents
Herbicidal 1,3-dioxanesInfo
- Publication number
- CA1101424A CA1101424A CA284,505A CA284505A CA1101424A CA 1101424 A CA1101424 A CA 1101424A CA 284505 A CA284505 A CA 284505A CA 1101424 A CA1101424 A CA 1101424A
- Authority
- CA
- Canada
- Prior art keywords
- hydrogen
- compound
- alkyl
- dioxane
- methyl
- 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.)
- Expired
Links
- 230000002363 herbicidal effect Effects 0.000 title abstract description 25
- 150000000093 1,3-dioxanes Chemical class 0.000 title description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 107
- 150000001875 compounds Chemical class 0.000 claims abstract description 89
- 239000001257 hydrogen Substances 0.000 claims abstract description 47
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 37
- 239000011541 reaction mixture Substances 0.000 claims description 36
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- -1 polymethylene Polymers 0.000 claims description 14
- 235000010469 Glycine max Nutrition 0.000 claims description 12
- 244000068988 Glycine max Species 0.000 claims description 12
- 244000105624 Arachis hypogaea Species 0.000 claims description 10
- 229920000742 Cotton Polymers 0.000 claims description 10
- 241000209140 Triticum Species 0.000 claims description 10
- 235000021307 Triticum Nutrition 0.000 claims description 10
- 235000020232 peanut Nutrition 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 8
- 125000001188 haloalkyl group Chemical group 0.000 claims description 8
- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- 150000001340 alkali metals Chemical class 0.000 claims description 7
- 239000002585 base Substances 0.000 claims description 6
- VCKSNYNNVSOWEE-UHFFFAOYSA-N 1,3-dioxan-5-ol Chemical class OC1COCOC1 VCKSNYNNVSOWEE-UHFFFAOYSA-N 0.000 claims description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 230000008635 plant growth Effects 0.000 claims description 4
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 3
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- 244000299507 Gossypium hirsutum Species 0.000 claims description 2
- 239000003377 acid catalyst Substances 0.000 claims description 2
- 230000003405 preventing effect Effects 0.000 claims description 2
- 150000003388 sodium compounds Chemical class 0.000 claims description 2
- 125000003003 spiro group Chemical group 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 1
- 125000005002 aryl methyl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract description 3
- 125000000532 dioxanyl group Chemical group 0.000 abstract description 3
- 230000012010 growth Effects 0.000 abstract description 3
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- 239000000203 mixture Substances 0.000 description 62
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 45
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 38
- 239000000243 solution Substances 0.000 description 27
- 238000001228 spectrum Methods 0.000 description 23
- 239000007788 liquid Substances 0.000 description 22
- 238000004458 analytical method Methods 0.000 description 21
- 239000000543 intermediate Substances 0.000 description 21
- 239000000706 filtrate Substances 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 244000075850 Avena orientalis Species 0.000 description 17
- 238000004821 distillation Methods 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 16
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 14
- 239000003921 oil Substances 0.000 description 13
- 235000019198 oils Nutrition 0.000 description 13
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
- 241000196324 Embryophyta Species 0.000 description 11
- 238000009472 formulation Methods 0.000 description 11
- 238000010992 reflux Methods 0.000 description 11
- 229960003010 sodium sulfate Drugs 0.000 description 11
- 229910052938 sodium sulfate Inorganic materials 0.000 description 11
- 235000011152 sodium sulphate Nutrition 0.000 description 11
- 240000007594 Oryza sativa Species 0.000 description 10
- 235000007164 Oryza sativa Nutrition 0.000 description 10
- 239000007864 aqueous solution Substances 0.000 description 10
- 239000007795 chemical reaction product Substances 0.000 description 10
- 239000010410 layer Substances 0.000 description 10
- 229920006395 saturated elastomer Polymers 0.000 description 10
- VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical group C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 description 9
- 235000007320 Avena fatua Nutrition 0.000 description 9
- 235000007319 Avena orientalis Nutrition 0.000 description 9
- 235000001602 Digitaria X umfolozi Nutrition 0.000 description 9
- 240000003176 Digitaria ciliaris Species 0.000 description 9
- 235000017898 Digitaria ciliaris Nutrition 0.000 description 9
- 235000005476 Digitaria cruciata Nutrition 0.000 description 9
- 235000006830 Digitaria didactyla Nutrition 0.000 description 9
- 235000005804 Digitaria eriantha ssp. eriantha Nutrition 0.000 description 9
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 9
- 235000014716 Eleusine indica Nutrition 0.000 description 9
- 241000219146 Gossypium Species 0.000 description 9
- 235000003228 Lactuca sativa Nutrition 0.000 description 9
- 235000009566 rice Nutrition 0.000 description 9
- 235000017060 Arachis glabrata Nutrition 0.000 description 8
- 235000010777 Arachis hypogaea Nutrition 0.000 description 8
- 235000018262 Arachis monticola Nutrition 0.000 description 8
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 8
- 241001355178 Setaria faberi Species 0.000 description 8
- 240000006410 Sida spinosa Species 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 240000003768 Solanum lycopersicum Species 0.000 description 8
- 235000021536 Sugar beet Nutrition 0.000 description 8
- 235000005373 Uvularia sessilifolia Nutrition 0.000 description 8
- 240000008042 Zea mays Species 0.000 description 8
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 8
- 238000004587 chromatography analysis Methods 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 239000007789 gas Substances 0.000 description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
- 241000219198 Brassica Species 0.000 description 7
- 235000003351 Brassica cretica Nutrition 0.000 description 7
- 235000003343 Brassica rupestris Nutrition 0.000 description 7
- 241001148727 Bromus tectorum Species 0.000 description 7
- 235000003255 Carthamus tinctorius Nutrition 0.000 description 7
- 244000020518 Carthamus tinctorius Species 0.000 description 7
- 244000277285 Cassia obtusifolia Species 0.000 description 7
- 235000006719 Cassia obtusifolia Nutrition 0.000 description 7
- 244000058871 Echinochloa crus-galli Species 0.000 description 7
- 240000005979 Hordeum vulgare Species 0.000 description 7
- 235000007340 Hordeum vulgare Nutrition 0.000 description 7
- 240000001549 Ipomoea eriocarpa Species 0.000 description 7
- 235000005146 Ipomoea eriocarpa Nutrition 0.000 description 7
- 240000008415 Lactuca sativa Species 0.000 description 7
- 241000219782 Sesbania Species 0.000 description 7
- 235000017016 Setaria faberi Nutrition 0.000 description 7
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 7
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 150000004862 dioxolanes Chemical class 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 235000010460 mustard Nutrition 0.000 description 7
- 239000011780 sodium chloride Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 235000014552 Cassia tora Nutrition 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 6
- 150000002431 hydrogen Chemical group 0.000 description 6
- 239000002480 mineral oil Substances 0.000 description 6
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 6
- 239000002689 soil Substances 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- VQRBXYBBGHOGFT-UHFFFAOYSA-N 1-(chloromethyl)-2-methylbenzene Chemical compound CC1=CC=CC=C1CCl VQRBXYBBGHOGFT-UHFFFAOYSA-N 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- 244000062793 Sorghum vulgare Species 0.000 description 5
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 5
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 235000005822 corn Nutrition 0.000 description 5
- 150000002012 dioxanes Chemical class 0.000 description 5
- 229960004756 ethanol Drugs 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
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- 239000002245 particle Substances 0.000 description 5
- 150000002978 peroxides Chemical class 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 241000894007 species Species 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- ZNOKGRXACCSDPY-UHFFFAOYSA-N tungsten trioxide Chemical compound O=[W](=O)=O ZNOKGRXACCSDPY-UHFFFAOYSA-N 0.000 description 5
- MOBRMRJUKNQBMY-UHFFFAOYSA-N 1-(chloromethyl)-2-fluorobenzene Chemical compound FC1=CC=CC=C1CCl MOBRMRJUKNQBMY-UHFFFAOYSA-N 0.000 description 4
- VAZNCFOEOCSGQL-UHFFFAOYSA-N OOOOOOOOOOOOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOOOOOOOOOOOO VAZNCFOEOCSGQL-UHFFFAOYSA-N 0.000 description 4
- 208000036366 Sensation of pressure Diseases 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
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- 238000004817 gas chromatography Methods 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- 239000012258 stirred mixture Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- 239000004563 wettable powder Substances 0.000 description 4
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 3
- INEJFAJHYRLCDJ-UHFFFAOYSA-N 2-methyl-2-[(2-methylphenyl)methoxy]propane-1,3-diol Chemical compound CC1=CC=CC=C1COC(C)(CO)CO INEJFAJHYRLCDJ-UHFFFAOYSA-N 0.000 description 3
- 239000005711 Benzoic acid Substances 0.000 description 3
- HFEFMUSTGZNOPY-UHFFFAOYSA-N OOOOOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOOOOO HFEFMUSTGZNOPY-UHFFFAOYSA-N 0.000 description 3
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- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
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- RNQWXOKSUCPOFS-UHFFFAOYSA-N 1,4-dioxan-2-ol Chemical class OC1COCCO1 RNQWXOKSUCPOFS-UHFFFAOYSA-N 0.000 description 2
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- PEEDFNMWQSLWRM-UHFFFAOYSA-N 2,4-dimethyl-1,3-dioxan-5-ol Chemical class CC1OCC(O)C(C)O1 PEEDFNMWQSLWRM-UHFFFAOYSA-N 0.000 description 2
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- JJRYPZMXNLLZFH-GFUIURDCSA-N (6R)-dehydrovomifoliol Chemical compound CC(=O)\C=C\[C@]1(O)C(C)=CC(=O)CC1(C)C JJRYPZMXNLLZFH-GFUIURDCSA-N 0.000 description 1
- GJYMQFMQRRNLCY-ONEGZZNKSA-N (e)-pent-3-en-2-ol Chemical compound C\C=C\C(C)O GJYMQFMQRRNLCY-ONEGZZNKSA-N 0.000 description 1
- WYCRQIULMFHSGL-UHFFFAOYSA-N 1,1-dimethoxypentan-3-one Chemical compound CCC(=O)CC(OC)OC WYCRQIULMFHSGL-UHFFFAOYSA-N 0.000 description 1
- YAXKTBLXMTYWDQ-UHFFFAOYSA-N 1,2,3-butanetriol Chemical class CC(O)C(O)CO YAXKTBLXMTYWDQ-UHFFFAOYSA-N 0.000 description 1
- 150000000185 1,3-diols Chemical class 0.000 description 1
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- AWDLBZUXUNIODN-UHFFFAOYSA-N 2,3-dimethylbut-3-en-2-ol Chemical compound CC(=C)C(C)(C)O AWDLBZUXUNIODN-UHFFFAOYSA-N 0.000 description 1
- GANBJDIOIDQSGI-UHFFFAOYSA-N 2-(chloromethyl)furan Chemical compound ClCC1=CC=CO1 GANBJDIOIDQSGI-UHFFFAOYSA-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
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- MQDHUKPLYSNZDA-UHFFFAOYSA-N 2-ethyl-4,5-dimethyl-4-[1-[(2-methylphenyl)methoxy]ethyl]-1,3-dioxolane Chemical compound O1C(CC)OC(C)C1(C)C(C)OCC1=CC=CC=C1C MQDHUKPLYSNZDA-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
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- IKDJETWTVWBJRW-UHFFFAOYSA-N 3-methylpent-1-en-2-ol Chemical compound CCC(C)C(O)=C IKDJETWTVWBJRW-UHFFFAOYSA-N 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
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- 235000014700 Brassica juncea var napiformis Nutrition 0.000 description 1
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- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 1
- 244000045232 Canavalia ensiformis Species 0.000 description 1
- WLYGSPLCNKYESI-RSUQVHIMSA-N Carthamin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1[C@@]1(O)C(O)=C(C(=O)\C=C\C=2C=CC(O)=CC=2)C(=O)C(\C=C\2C([C@](O)([C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O)C(O)=C(C(=O)\C=C\C=3C=CC(O)=CC=3)C/2=O)=O)=C1O WLYGSPLCNKYESI-RSUQVHIMSA-N 0.000 description 1
- 241000208809 Carthamus Species 0.000 description 1
- 244000298479 Cichorium intybus Species 0.000 description 1
- 235000007542 Cichorium intybus Nutrition 0.000 description 1
- 235000017896 Digitaria Nutrition 0.000 description 1
- 241001303487 Digitaria <clam> Species 0.000 description 1
- 101000864663 Drosophila melanogaster ATP-dependent RNA helicase DHX8 Proteins 0.000 description 1
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 1
- 235000009432 Gossypium hirsutum Nutrition 0.000 description 1
- 241000207890 Ipomoea purpurea Species 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 238000003820 Medium-pressure liquid chromatography Methods 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- JLNTWVDSQRNWFU-UHFFFAOYSA-N OOOOOOO Chemical compound OOOOOOO JLNTWVDSQRNWFU-UHFFFAOYSA-N 0.000 description 1
- JWOLLWQJKQOEOL-UHFFFAOYSA-N OOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOO JWOLLWQJKQOEOL-UHFFFAOYSA-N 0.000 description 1
- RRCYYLHJWRYWEI-UHFFFAOYSA-N OOOOOOOOOOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOOOOOOOOOO RRCYYLHJWRYWEI-UHFFFAOYSA-N 0.000 description 1
- IVDBGHPEQSTHRK-UHFFFAOYSA-N OOOOOOOOOOOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOOOOOOOOOOO IVDBGHPEQSTHRK-UHFFFAOYSA-N 0.000 description 1
- 235000011999 Panicum crusgalli Nutrition 0.000 description 1
- 244000100170 Phaseolus lunatus Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 1
- 244000275012 Sesbania cannabina Species 0.000 description 1
- 241000533293 Sesbania emerus Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 235000007244 Zea mays Nutrition 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
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- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 239000000538 analytical sample Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 125000005997 bromomethyl group Chemical group 0.000 description 1
- RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000007931 coated granule Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000002301 combined effect Effects 0.000 description 1
- 238000005056 compaction Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 235000008504 concentrate Nutrition 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- BBGKDYHZQOSNMU-UHFFFAOYSA-N dicyclohexano-18-crown-6 Chemical compound O1CCOCCOC2CCCCC2OCCOCCOC2CCCCC21 BBGKDYHZQOSNMU-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 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
- 238000010828 elution Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000727 fraction Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- STEPQTYSZVCJPV-UHFFFAOYSA-N metazachlor Chemical compound CC1=CC=CC(C)=C1N(C(=O)CCl)CN1N=CC=C1 STEPQTYSZVCJPV-UHFFFAOYSA-N 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- RDIMTXDFGHNINN-UHFFFAOYSA-N panaxytriol Chemical compound CCCCCCCC(O)C(O)CC#CC#CC(O)C=C RDIMTXDFGHNINN-UHFFFAOYSA-N 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 229940057007 petroleum distillate Drugs 0.000 description 1
- 229920000056 polyoxyethylene ether Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002594 sorbent Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
-
- 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
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
- A01N43/32—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms six-membered rings
-
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/14—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by free hydroxyl radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
- C07D317/20—Free hydroxyl or mercaptan
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
- C07D317/22—Radicals substituted by singly bound oxygen or sulfur atoms etherified
-
- 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
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/719,311 US4035178A (en) | 1976-08-31 | 1976-08-31 | Herbicidal 1,3-dioxanes |
| US719,311 | 1976-08-31 | ||
| US81191877A | 1977-06-30 | 1977-06-30 | |
| US811,918 | 1977-06-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1101424A true CA1101424A (en) | 1981-05-19 |
Family
ID=27110058
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA284,505A Expired CA1101424A (en) | 1976-08-31 | 1977-08-11 | Herbicidal 1,3-dioxanes |
Country Status (19)
| Country | Link |
|---|---|
| JP (1) | JPS5337671A (en)) |
| AR (1) | AR219717A1 (en)) |
| AU (1) | AU511199B2 (en)) |
| BR (1) | BR7705818A (en)) |
| CA (1) | CA1101424A (en)) |
| CH (1) | CH628627A5 (en)) |
| DE (1) | DE2739067A1 (en)) |
| DK (1) | DK384177A (en)) |
| ES (1) | ES461972A1 (en)) |
| FR (1) | FR2363566A1 (en)) |
| GB (1) | GB1557103A (en)) |
| IE (1) | IE45464B1 (en)) |
| IL (1) | IL52701A (en)) |
| IN (1) | IN146343B (en)) |
| IT (1) | IT1086066B (en)) |
| LU (1) | LU78058A1 (en)) |
| NL (1) | NL7709537A (en)) |
| RO (2) | RO79502A (en)) |
| SU (1) | SU741777A3 (en)) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4465503A (en) * | 1979-08-07 | 1984-08-14 | Ube Industries Ltd. | Diphenyl ether derivatives, process for preparing the same and herbicidal compositions containing the same |
| CH659166GA3 (en)) * | 1985-10-07 | 1987-01-15 | ||
| GB8713745D0 (en) * | 1987-06-12 | 1987-07-15 | Scras | Aminoacylates of glycerol |
| US4987081A (en) * | 1987-07-10 | 1991-01-22 | Gb Biotech Inc. | Chemical/biological process to oxidize multimetallic sulphide ores |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE789105A (fr) * | 1971-09-21 | 1973-03-21 | Fmc Corp | Dioxannes substitues et leur application comme |
| US4035178A (en) * | 1976-08-31 | 1977-07-12 | Fmc Corporation | Herbicidal 1,3-dioxanes |
-
1977
- 1977-07-11 IN IN1052/CAL/77A patent/IN146343B/en unknown
- 1977-08-11 CA CA284,505A patent/CA1101424A/en not_active Expired
- 1977-08-11 IL IL52701A patent/IL52701A/xx unknown
- 1977-08-12 AU AU27867/77A patent/AU511199B2/en not_active Expired
- 1977-08-15 IE IE1702/77A patent/IE45464B1/en unknown
- 1977-08-25 GB GB35739/77A patent/GB1557103A/en not_active Expired
- 1977-08-29 AR AR268980A patent/AR219717A1/es active
- 1977-08-29 IT IT27058/77A patent/IT1086066B/it active
- 1977-08-30 SU SU772514691A patent/SU741777A3/ru active
- 1977-08-30 JP JP10329077A patent/JPS5337671A/ja active Pending
- 1977-08-30 DK DK384177A patent/DK384177A/da unknown
- 1977-08-30 DE DE19772739067 patent/DE2739067A1/de not_active Withdrawn
- 1977-08-30 ES ES461972A patent/ES461972A1/es not_active Expired
- 1977-08-30 FR FR7726342A patent/FR2363566A1/fr active Granted
- 1977-08-30 NL NL7709537A patent/NL7709537A/xx not_active Application Discontinuation
- 1977-08-31 RO RO77100267A patent/RO79502A/ro unknown
- 1977-08-31 BR BR7705818A patent/BR7705818A/pt unknown
- 1977-08-31 RO RO7791505A patent/RO74637A/ro unknown
- 1977-08-31 CH CH1061677A patent/CH628627A5/de not_active IP Right Cessation
- 1977-08-31 LU LU78058A patent/LU78058A1/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL52701A0 (en) | 1977-10-31 |
| IL52701A (en) | 1982-03-31 |
| DE2739067A1 (de) | 1978-03-02 |
| AU511199B2 (en) | 1980-07-31 |
| IE45464L (en) | 1978-02-28 |
| IT1086066B (it) | 1985-05-28 |
| IE45464B1 (en) | 1982-08-25 |
| RO79502A (ro) | 1982-07-06 |
| JPS5337671A (en) | 1978-04-06 |
| AU2786777A (en) | 1979-02-15 |
| AR219717A1 (es) | 1980-09-15 |
| GB1557103A (en) | 1979-12-05 |
| FR2363566A1 (fr) | 1978-03-31 |
| BR7705818A (pt) | 1978-06-27 |
| FR2363566B1 (en)) | 1982-03-26 |
| CH628627A5 (en) | 1982-03-15 |
| ES461972A1 (es) | 1978-11-01 |
| SU741777A3 (ru) | 1980-06-15 |
| RO74637A (ro) | 1980-10-30 |
| NL7709537A (nl) | 1978-03-02 |
| IN146343B (en)) | 1979-05-05 |
| LU78058A1 (en)) | 1978-04-27 |
| DK384177A (da) | 1978-03-01 |
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Effective date: 19980519 |