NO782906L - Herbicide fosfonater. - Google Patents
Herbicide fosfonater.Info
- Publication number
- NO782906L NO782906L NO782906A NO782906A NO782906L NO 782906 L NO782906 L NO 782906L NO 782906 A NO782906 A NO 782906A NO 782906 A NO782906 A NO 782906A NO 782906 L NO782906 L NO 782906L
- Authority
- NO
- Norway
- Prior art keywords
- carbon atoms
- acetate
- methylethyl
- connection according
- phosphinyl
- Prior art date
Links
- 230000002363 herbicidal effect Effects 0.000 title claims description 7
- 239000004009 herbicide Substances 0.000 title description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 72
- 150000001875 compounds Chemical class 0.000 claims description 67
- 125000003545 alkoxy group Chemical group 0.000 claims description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 239000000460 chlorine Chemical group 0.000 claims description 24
- 229910052801 chlorine Chemical group 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- -1 phenoxy, phenoxy Chemical group 0.000 claims description 21
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 16
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 239000001301 oxygen Substances 0.000 claims description 16
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- IGNNDVPMNMFOMD-UHFFFAOYSA-N butan-2-yl 2,2-dichloro-2-diethoxyphosphorylacetate Chemical group CCOP(=O)(OCC)C(Cl)(Cl)C(=O)OC(C)CC IGNNDVPMNMFOMD-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- ILUUJUQOLRFONR-UHFFFAOYSA-N propan-2-yl 2-[bis(2-methoxyethoxy)phosphoryl]-2-chloroacetate Chemical compound COCCOP(=O)(OCCOC)C(Cl)C(=O)OC(C)C ILUUJUQOLRFONR-UHFFFAOYSA-N 0.000 claims description 4
- 229910052717 sulfur Chemical group 0.000 claims description 4
- 239000011593 sulfur Chemical group 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- QMUYSDIKMKDGBE-UHFFFAOYSA-N butan-2-yl 2-chloro-2-diethoxyphosphorylacetate Chemical group CCOP(=O)(OCC)C(Cl)C(=O)OC(C)CC QMUYSDIKMKDGBE-UHFFFAOYSA-N 0.000 claims description 3
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- FXOXTSBAVMKGNI-UHFFFAOYSA-N (2-butan-2-yloxy-1,1-dichloro-2-oxoethyl)-ethoxyphosphinic acid;sodium Chemical group [Na].CCOP(O)(=O)C(Cl)(Cl)C(=O)OC(C)CC FXOXTSBAVMKGNI-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- BMQSAOMYWNPYOZ-UHFFFAOYSA-N propan-2-yl 2-[bis(2-methoxyethoxy)phosphoryl]-2,2-dichloroacetate Chemical group COCCOP(=O)(OCCOC)C(Cl)(Cl)C(=O)OC(C)C BMQSAOMYWNPYOZ-UHFFFAOYSA-N 0.000 claims description 2
- CYYDFNRKKNQJGM-UHFFFAOYSA-N propan-2-yl 2-chloro-2-diethoxyphosphorylacetate Chemical group CCOP(=O)(OCC)C(Cl)C(=O)OC(C)C CYYDFNRKKNQJGM-UHFFFAOYSA-N 0.000 claims description 2
- 229910004013 NO 2 Inorganic materials 0.000 claims 1
- 125000006015 bromomethoxy group Chemical group 0.000 claims 1
- NLVJAOFZNPUCOY-UHFFFAOYSA-N butan-2-yl 2-chloro-2-di(propan-2-yloxy)phosphorylacetate Chemical group CCC(C)OC(=O)C(Cl)P(=O)(OC(C)C)OC(C)C NLVJAOFZNPUCOY-UHFFFAOYSA-N 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- QQMLYBLGJSLYKM-UHFFFAOYSA-N propan-2-yl 2,2-dichloro-2-[diethylamino(ethoxy)phosphoryl]acetate Chemical group CCOP(=O)(N(CC)CC)C(Cl)(Cl)C(=O)OC(C)C QQMLYBLGJSLYKM-UHFFFAOYSA-N 0.000 claims 1
- NZDXIWJCLKQHBY-UHFFFAOYSA-N propan-2-yl 2,2-dichloro-2-di(butan-2-yloxy)phosphorylacetate Chemical group CCC(C)OP(=O)(OC(C)CC)C(Cl)(Cl)C(=O)OC(C)C NZDXIWJCLKQHBY-UHFFFAOYSA-N 0.000 claims 1
- ZSQPLDCETDLSKM-UHFFFAOYSA-N propan-2-yl 2,2-dichloro-2-di(propan-2-yloxy)phosphorylacetate Chemical group CC(C)OC(=O)C(Cl)(Cl)P(=O)(OC(C)C)OC(C)C ZSQPLDCETDLSKM-UHFFFAOYSA-N 0.000 claims 1
- BUUJPUOQBKUEAM-UHFFFAOYSA-N propan-2-yl 2,2-dichloro-2-dipropoxyphosphorylacetate Chemical group CCCOP(=O)(OCCC)C(Cl)(Cl)C(=O)OC(C)C BUUJPUOQBKUEAM-UHFFFAOYSA-N 0.000 claims 1
- RMWAPPNOZYSURY-UHFFFAOYSA-N propan-2-yl 2-chloro-2-[diethylamino(ethoxy)phosphoryl]acetate Chemical group CCOP(=O)(N(CC)CC)C(Cl)C(=O)OC(C)C RMWAPPNOZYSURY-UHFFFAOYSA-N 0.000 claims 1
- LJOPKIOOUVXUTC-UHFFFAOYSA-N propan-2-yl 2-chloro-2-[ethoxy(ethylamino)phosphoryl]acetate Chemical group CCNP(=O)(OCC)C(Cl)C(=O)OC(C)C LJOPKIOOUVXUTC-UHFFFAOYSA-N 0.000 claims 1
- NHDHANSOBPLDHE-UHFFFAOYSA-N propan-2-yl 2-chloro-2-di(butan-2-yloxy)phosphorylacetate Chemical group CCC(C)OP(=O)(OC(C)CC)C(Cl)C(=O)OC(C)C NHDHANSOBPLDHE-UHFFFAOYSA-N 0.000 claims 1
- MGZXSUDADGAWBV-UHFFFAOYSA-N propan-2-yl 2-chloro-2-di(propan-2-yloxy)phosphorylacetate Chemical group CC(C)OC(=O)C(Cl)P(=O)(OC(C)C)OC(C)C MGZXSUDADGAWBV-UHFFFAOYSA-N 0.000 claims 1
- 244000062793 Sorghum vulgare Species 0.000 description 24
- 241000196324 Embryophyta Species 0.000 description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 235000019713 millet Nutrition 0.000 description 16
- 239000002904 solvent Substances 0.000 description 14
- 239000008187 granular material Substances 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- 244000068988 Glycine max Species 0.000 description 11
- 235000010469 Glycine max Nutrition 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- 239000002689 soil Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- 240000007594 Oryza sativa Species 0.000 description 9
- 235000007164 Oryza sativa Nutrition 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 235000009566 rice Nutrition 0.000 description 9
- 238000011282 treatment Methods 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 8
- 239000008188 pellet Substances 0.000 description 8
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
- 229920000742 Cotton Polymers 0.000 description 7
- 244000299507 Gossypium hirsutum Species 0.000 description 7
- 241000209140 Triticum Species 0.000 description 7
- 235000021307 Triticum Nutrition 0.000 description 7
- 240000008042 Zea mays Species 0.000 description 7
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 7
- 239000008280 blood Substances 0.000 description 7
- 210000004369 blood Anatomy 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 235000009051 Ambrosia paniculata var. peruviana Nutrition 0.000 description 5
- 235000003097 Artemisia absinthium Nutrition 0.000 description 5
- 240000001851 Artemisia dracunculus Species 0.000 description 5
- 235000017731 Artemisia dracunculus ssp. dracunculus Nutrition 0.000 description 5
- 235000003261 Artemisia vulgaris Nutrition 0.000 description 5
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 5
- 244000037364 Cinnamomum aromaticum Species 0.000 description 5
- 235000014489 Cinnamomum aromaticum Nutrition 0.000 description 5
- 244000058871 Echinochloa crus-galli Species 0.000 description 5
- 235000011999 Panicum crusgalli Nutrition 0.000 description 5
- 240000002439 Sorghum halepense Species 0.000 description 5
- 235000021536 Sugar beet Nutrition 0.000 description 5
- 239000001138 artemisia absinthium Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000004033 plastic Substances 0.000 description 5
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 5
- 241000209761 Avena Species 0.000 description 4
- 235000007319 Avena orientalis Nutrition 0.000 description 4
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 241001268782 Paspalum dilatatum Species 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000004495 emulsifiable concentrate Substances 0.000 description 4
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 235000009973 maize Nutrition 0.000 description 4
- 238000001819 mass spectrum Methods 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 235000007320 Avena fatua Nutrition 0.000 description 3
- 241000209764 Avena fatua Species 0.000 description 3
- 244000201986 Cassia tora Species 0.000 description 3
- 235000014552 Cassia tora Nutrition 0.000 description 3
- 241000234653 Cyperus Species 0.000 description 3
- 240000008853 Datura stramonium Species 0.000 description 3
- 244000152970 Digitaria sanguinalis Species 0.000 description 3
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 3
- 240000001439 Opuntia Species 0.000 description 3
- 235000013389 Opuntia humifusa var. humifusa Nutrition 0.000 description 3
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 3
- 241000209049 Poa pratensis Species 0.000 description 3
- 241001355178 Setaria faberi Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 241001506766 Xanthium Species 0.000 description 3
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
- 238000005660 chlorination reaction Methods 0.000 description 3
- 235000005822 corn Nutrition 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 231100001184 nonphytotoxic Toxicity 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 229960000278 theophylline Drugs 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- XMTQQYYKAHVGBJ-UHFFFAOYSA-N 3-(3,4-DICHLOROPHENYL)-1,1-DIMETHYLUREA Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XMTQQYYKAHVGBJ-UHFFFAOYSA-N 0.000 description 2
- CTSLUCNDVMMDHG-UHFFFAOYSA-N 5-bromo-3-(butan-2-yl)-6-methylpyrimidine-2,4(1H,3H)-dione Chemical compound CCC(C)N1C(=O)NC(C)=C(Br)C1=O CTSLUCNDVMMDHG-UHFFFAOYSA-N 0.000 description 2
- 240000006995 Abutilon theophrasti Species 0.000 description 2
- 244000291564 Allium cepa Species 0.000 description 2
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 2
- 244000078782 Brassica arvensis Species 0.000 description 2
- 235000008427 Brassica arvensis Nutrition 0.000 description 2
- 235000011292 Brassica rapa Nutrition 0.000 description 2
- 101100178984 Caenorhabditis elegans hyl-2 gene Proteins 0.000 description 2
- 244000075634 Cyperus rotundus Species 0.000 description 2
- 235000016854 Cyperus rotundus Nutrition 0.000 description 2
- 235000017896 Digitaria Nutrition 0.000 description 2
- 241001303487 Digitaria <clam> Species 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 240000008620 Fagopyrum esculentum Species 0.000 description 2
- 235000009419 Fagopyrum esculentum Nutrition 0.000 description 2
- 206010053759 Growth retardation Diseases 0.000 description 2
- 240000007218 Ipomoea hederacea Species 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 2
- 244000046052 Phaseolus vulgaris Species 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 241000220317 Rosa Species 0.000 description 2
- 240000006410 Sida spinosa Species 0.000 description 2
- 240000007807 Sisymbrium officinale Species 0.000 description 2
- 239000005708 Sodium hypochlorite Substances 0.000 description 2
- 239000005864 Sulphur Chemical group 0.000 description 2
- 240000007313 Tilia cordata Species 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 240000000359 Triticum dicoccon Species 0.000 description 2
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical class O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000005054 agglomeration Methods 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000004061 bleaching Methods 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- LWYTTXXBELOHPX-UHFFFAOYSA-N butan-2-yl 2-[[di(propan-2-yl)amino]-ethoxyphosphoryl]acetate Chemical compound CCOP(=O)(N(C(C)C)C(C)C)CC(=O)OC(C)CC LWYTTXXBELOHPX-UHFFFAOYSA-N 0.000 description 2
- CGJDPMPLJMPTEM-UHFFFAOYSA-N butan-2-yl 2-diethoxyphosphorylacetate Chemical compound CCOP(=O)(OCC)CC(=O)OC(C)CC CGJDPMPLJMPTEM-UHFFFAOYSA-N 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- WYKYKTKDBLFHCY-UHFFFAOYSA-N chloridazon Chemical compound O=C1C(Cl)=C(N)C=NN1C1=CC=CC=C1 WYKYKTKDBLFHCY-UHFFFAOYSA-N 0.000 description 2
- IVUXTESCPZUGJC-UHFFFAOYSA-N chloroxuron Chemical compound C1=CC(NC(=O)N(C)C)=CC=C1OC1=CC=C(Cl)C=C1 IVUXTESCPZUGJC-UHFFFAOYSA-N 0.000 description 2
- MZZBPDKVEFVLFF-UHFFFAOYSA-N cyanazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C#N)=N1 MZZBPDKVEFVLFF-UHFFFAOYSA-N 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000012010 growth Effects 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- 231100000001 growth retardation Toxicity 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- ZTMKADLOSYKWCA-UHFFFAOYSA-N lenacil Chemical compound O=C1NC=2CCCC=2C(=O)N1C1CCCCC1 ZTMKADLOSYKWCA-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000017074 necrotic cell death Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 150000002903 organophosphorus compounds Chemical class 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 229910052700 potassium Chemical group 0.000 description 2
- WJNRPILHGGKWCK-UHFFFAOYSA-N propazine Chemical compound CC(C)NC1=NC(Cl)=NC(NC(C)C)=N1 WJNRPILHGGKWCK-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 1
- HXKWSTRRCHTUEC-UHFFFAOYSA-N 2,4-Dichlorophenoxyaceticacid Chemical compound OC(=O)C(Cl)OC1=CC=C(Cl)C=C1 HXKWSTRRCHTUEC-UHFFFAOYSA-N 0.000 description 1
- HTYRTGGIOAMLRR-UHFFFAOYSA-N 5-amino-4-hydroxybenzene-1,3-disulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=CC(S(O)(=O)=O)=C1O HTYRTGGIOAMLRR-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- XKJMBINCVNINCA-UHFFFAOYSA-N Alfalone Chemical compound CON(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XKJMBINCVNINCA-UHFFFAOYSA-N 0.000 description 1
- 240000001592 Amaranthus caudatus Species 0.000 description 1
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 1
- 244000237956 Amaranthus retroflexus Species 0.000 description 1
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 1
- 235000005781 Avena Nutrition 0.000 description 1
- 244000075850 Avena orientalis Species 0.000 description 1
- 239000005476 Bentazone Substances 0.000 description 1
- 241000209202 Bromus secalinus Species 0.000 description 1
- 101100167062 Caenorhabditis elegans chch-3 gene Proteins 0.000 description 1
- 239000005493 Chloridazon (aka pyrazone) Substances 0.000 description 1
- 235000010523 Cicer arietinum Nutrition 0.000 description 1
- 244000045195 Cicer arietinum Species 0.000 description 1
- 244000301850 Cupressus sempervirens Species 0.000 description 1
- 239000005510 Diuron Substances 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 1
- 235000021506 Ipomoea Nutrition 0.000 description 1
- 241000207783 Ipomoea Species 0.000 description 1
- 239000005572 Lenacil Substances 0.000 description 1
- 239000005573 Linuron Substances 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 241000209082 Lolium Species 0.000 description 1
- 239000005583 Metribuzin Substances 0.000 description 1
- 241001024304 Mino Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- OQMBBFQZGJFLBU-UHFFFAOYSA-N Oxyfluorfen Chemical compound C1=C([N+]([O-])=O)C(OCC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 OQMBBFQZGJFLBU-UHFFFAOYSA-N 0.000 description 1
- 241000723554 Pontia occidentalis Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 235000002834 Sida rhombifolia Nutrition 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 235000012735 amaranth Nutrition 0.000 description 1
- 239000004178 amaranth Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- ZOMSMJKLGFBRBS-UHFFFAOYSA-N bentazone Chemical compound C1=CC=C2NS(=O)(=O)N(C(C)C)C(=O)C2=C1 ZOMSMJKLGFBRBS-UHFFFAOYSA-N 0.000 description 1
- CNBGNNVCVSKAQZ-UHFFFAOYSA-N benzidamine Natural products C12=CC=CC=C2C(OCCCN(C)C)=NN1CC1=CC=CC=C1 CNBGNNVCVSKAQZ-UHFFFAOYSA-N 0.000 description 1
- BYIRFGALWPURBH-UHFFFAOYSA-N butan-2-yl 2,2-dichloro-2-[dimethylamino(ethoxy)phosphoryl]acetate Chemical compound CCOP(=O)(N(C)C)C(Cl)(Cl)C(=O)OC(C)CC BYIRFGALWPURBH-UHFFFAOYSA-N 0.000 description 1
- UKWGBGRYZOHHEJ-UHFFFAOYSA-N butan-2-yl 2,2-dichloro-2-di(propan-2-yloxy)phosphorylacetate Chemical compound CCC(C)OC(=O)C(Cl)(Cl)P(=O)(OC(C)C)OC(C)C UKWGBGRYZOHHEJ-UHFFFAOYSA-N 0.000 description 1
- KWCVIUSPTOLYGC-UHFFFAOYSA-N butan-2-yl 2,2-dichloro-2-dichlorophosphorylacetate Chemical compound CCC(C)OC(=O)C(Cl)(Cl)P(Cl)(Cl)=O KWCVIUSPTOLYGC-UHFFFAOYSA-N 0.000 description 1
- AYUZHUMAYBBDJY-UHFFFAOYSA-N butan-2-yl 2-bromoacetate Chemical compound CCC(C)OC(=O)CBr AYUZHUMAYBBDJY-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 108700039708 galantide Proteins 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Chemical group 0.000 description 1
- 239000011630 iodine Chemical group 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- 230000002015 leaf growth Effects 0.000 description 1
- 239000003879 lubricant additive Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 229910001511 metal iodide Inorganic materials 0.000 description 1
- FOXFZRUHNHCZPX-UHFFFAOYSA-N metribuzin Chemical compound CSC1=NN=C(C(C)(C)C)C(=O)N1N FOXFZRUHNHCZPX-UHFFFAOYSA-N 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- KVKFRMCSXWQSNT-UHFFFAOYSA-N n,n'-dimethylethane-1,2-diamine Chemical compound CNCCNC KVKFRMCSXWQSNT-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- UUFIBXKHKNIZHL-UHFFFAOYSA-N n-diethoxyphosphanyl-n-propan-2-ylpropan-2-amine Chemical compound CCOP(OCC)N(C(C)C)C(C)C UUFIBXKHKNIZHL-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- FIKAKWIAUPDISJ-UHFFFAOYSA-L paraquat dichloride Chemical compound [Cl-].[Cl-].C1=C[N+](C)=CC=C1C1=CC=[N+](C)C=C1 FIKAKWIAUPDISJ-UHFFFAOYSA-L 0.000 description 1
- 235000020030 perry Nutrition 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000011591 potassium Chemical group 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- BFQADUKGSSNBQH-UHFFFAOYSA-N propan-2-yl 2,2-dichloro-2-[[di(propan-2-yl)amino]-ethoxyphosphoryl]acetate Chemical compound CCOP(=O)(N(C(C)C)C(C)C)C(Cl)(Cl)C(=O)OC(C)C BFQADUKGSSNBQH-UHFFFAOYSA-N 0.000 description 1
- XAGWENKTARJMLM-UHFFFAOYSA-N propan-2-yl 2-chloro-2-dipropoxyphosphorylacetate Chemical compound CCCOP(=O)(OCCC)C(Cl)C(=O)OC(C)C XAGWENKTARJMLM-UHFFFAOYSA-N 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000007226 seed germination Effects 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- RVULBHWZFCBODE-UHFFFAOYSA-M sodium;5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate Chemical class [Na+].C1=C([N+]([O-])=O)C(C(=O)[O-])=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 RVULBHWZFCBODE-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- BXDAOUXDMHXPDI-UHFFFAOYSA-N trifluoperazine hydrochloride Chemical compound [H+].[H+].[Cl-].[Cl-].C1CN(C)CCN1CCCN1C2=CC(C(F)(F)F)=CC=C2SC2=CC=CC=C21 BXDAOUXDMHXPDI-UHFFFAOYSA-N 0.000 description 1
- 229940035893 uracil Drugs 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
-
- 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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/44—Amides thereof
- C07F9/4403—Amides thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4407—Amides of acyclic saturated acids which can have further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/44—Amides thereof
- C07F9/4461—Amides thereof the amide moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4465—Amides thereof the amide moiety containing a substituent or a structure which is considered as characteristic of aliphatic amines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Dentistry (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US82821377A | 1977-08-26 | 1977-08-26 | |
| US91475678A | 1978-06-14 | 1978-06-14 | |
| US91738978A | 1978-06-23 | 1978-06-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO782906L true NO782906L (no) | 1979-02-27 |
Family
ID=27420202
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO782906A NO782906L (no) | 1977-08-26 | 1978-08-25 | Herbicide fosfonater. |
Country Status (15)
| Country | Link |
|---|---|
| EP (1) | EP0001018A1 (de) |
| JP (1) | JPS5444618A (de) |
| AT (1) | AT361246B (de) |
| AU (1) | AU3920078A (de) |
| BR (1) | BR7805516A (de) |
| DK (1) | DK324778A (de) |
| ES (1) | ES472862A1 (de) |
| FI (1) | FI782606A7 (de) |
| GB (1) | GB2004282A (de) |
| GR (1) | GR65203B (de) |
| IL (1) | IL55437A0 (de) |
| IT (1) | IT1098200B (de) |
| NO (1) | NO782906L (de) |
| PL (1) | PL111716B1 (de) |
| PT (1) | PT68479A (de) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA828650B (en) * | 1981-12-01 | 1983-09-28 | Hunt Chem Corp Philip A | Herbicidal compositions and method using phosphonalkanoic acids, esters and salts thereof |
| DE3313070A1 (de) * | 1983-04-12 | 1984-10-18 | Bayer Ag, 5090 Leverkusen | Chlorierte phosphorylmethylcarbonyl-derivate, verfahren zu ihrer herstellung und ihre verwendung in pflanzenschutmitteln |
| DE3425701A1 (de) * | 1984-07-12 | 1986-01-16 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von chlorierten phosphorylmethylcarbonyl-derivaten und neue zwischenprodukte zu ihrer herstellung |
| DE3502997A1 (de) * | 1985-01-30 | 1986-07-31 | Bayer Ag, 5090 Leverkusen | Verfahren zur verfestigung von geologischen formationen |
| US5025002A (en) * | 1988-09-01 | 1991-06-18 | Bromine Compounds Ltd. | Process for control of microorganisms with phosphorus-based compositions |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1071755A (fr) * | 1951-09-25 | 1954-09-06 | Ciba Geigy | Nouveaux composés organiques halogénés et phosphorés, et procédé pour leur préparation |
| FR1156652A (fr) * | 1955-09-12 | 1958-05-20 | Ciba Geigy | Nouveaux composés renfermant un halogène et du phosphore, leur préparation et leur utilisation |
| DE1948475A1 (de) * | 1968-09-26 | 1970-05-27 | Procter & Gamble | Verfahren zur Herstellung von halogenierten Methylendiphosphonaten,Malonaten und Phosphonoacetaten |
-
1978
- 1978-07-20 DK DK324778A patent/DK324778A/da unknown
- 1978-08-24 AU AU39200/78A patent/AU3920078A/en active Pending
- 1978-08-24 IT IT26997/78A patent/IT1098200B/it active
- 1978-08-24 JP JP10238778A patent/JPS5444618A/ja active Pending
- 1978-08-25 EP EP78300324A patent/EP0001018A1/de not_active Withdrawn
- 1978-08-25 FI FI782606A patent/FI782606A7/fi not_active Application Discontinuation
- 1978-08-25 GB GB7834620A patent/GB2004282A/en not_active Withdrawn
- 1978-08-25 BR BR7805516A patent/BR7805516A/pt unknown
- 1978-08-25 NO NO782906A patent/NO782906L/no unknown
- 1978-08-25 ES ES472862A patent/ES472862A1/es not_active Expired
- 1978-08-25 PT PT68479A patent/PT68479A/pt unknown
- 1978-08-25 PL PL1978209225A patent/PL111716B1/pl unknown
- 1978-08-25 IL IL7855437A patent/IL55437A0/xx unknown
- 1978-08-25 GR GR57077A patent/GR65203B/el unknown
- 1978-08-28 AT AT625778A patent/AT361246B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| IT1098200B (it) | 1985-09-07 |
| GR65203B (en) | 1980-07-29 |
| AU3920078A (en) | 1980-02-28 |
| IT7826997A0 (it) | 1978-08-24 |
| FI782606A7 (fi) | 1979-02-27 |
| BR7805516A (pt) | 1979-04-17 |
| EP0001018A1 (de) | 1979-03-07 |
| ATA625778A (de) | 1980-07-15 |
| GB2004282A (en) | 1979-03-28 |
| DK324778A (da) | 1979-02-27 |
| ES472862A1 (es) | 1979-10-16 |
| IL55437A0 (en) | 1978-10-31 |
| PT68479A (en) | 1978-09-01 |
| PL209225A1 (pl) | 1979-06-04 |
| JPS5444618A (en) | 1979-04-09 |
| AT361246B (de) | 1981-02-25 |
| PL111716B1 (en) | 1980-09-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4315765A (en) | Trialkylsulfonium salts of n-phosphonomethylglycine and their use as plant growth regulators and herbicides | |
| EP0184385B1 (de) | N-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-3-trifluoromethylpyridin-2-sulfonamide oder Salze davon, diese enthaltendes herbizides Mittel und Verfahren zur Herstellung dieser Verbindung | |
| AU593097B2 (en) | Sulfur containing cyclohexanedione derivatives and intermediates thereof | |
| RO111006B1 (ro) | Derivati de 2-cian-1,3-diona, procedee de preparare a acestora, compozitie erbicida si metoda pentru controlul cresterii buruienilor | |
| US4322375A (en) | 2-Substituted 5-phenoxyphenylphosphonic acid derivatives | |
| DK174545B1 (da) | Pyridinsulfonylurinstofderivater, middel til kontrol med væksten af uønsket vegetation, fremgangsmåde til kontrol med væksten af sådan vegetation sammt mellemprodukter til fremstilling af de nævnte derivater | |
| US4384880A (en) | Trialkylsulfonium salts of N-phosphonomethyl-glycine and their use as plant growth regulators and herbicides | |
| NZ201356A (en) | Phosphonium salts of n-phosphonomethyl glycine | |
| US4341549A (en) | Phosphonium salts of N-phosphonomethylglycine and their use as herbicides and plant growth regulants | |
| US4626276A (en) | Herbicidal trans-2-[(3-chloroallyloxyimino)alkyl]-5-(substitutedsulfinylalkyl)-cyclohexane-1,3-diones and derivatives thereof | |
| NO782906L (no) | Herbicide fosfonater. | |
| HU214645B (hu) | 1-amino-3-fenil-uracil-származékok, előállításuk, alkalmazásuk gyomirtóként, deszikkánsként és lombtalanítóként, ilyen készítmények, valamint eljárás utóbbiak előállítására | |
| NO782905L (no) | Herbicide fosfonater. | |
| US4692185A (en) | N-(ortho-substituted) benzyl, 3-trifluoromethylphenoxy nicotinamides as herbicides | |
| US5306695A (en) | Haloalkoxy-substituted benzoylcyclohexanediones as herbicides and plant growth regulators | |
| EP0073040A2 (de) | Organische Phosphorverbindungen und ihre Herstellung und Verwendung | |
| US4217312A (en) | 1-Alkyl-2,2-dichloro-2(phosphinyl)acetates | |
| US4192669A (en) | Herbicidal ethers | |
| EP0052473B1 (de) | N-Substituierte Phenyl-1-methylcyclopropancarboxamide, ihre Herstellung und Verwendung | |
| JPS6325588B2 (de) | ||
| EP0072253B1 (de) | Trifluoromethanesulfonanilide und deren Produktion und Verwendung | |
| EP0109311B1 (de) | N,N-Dialkyl-2-(4'-substituierte-1-naphthoxy)propionamide | |
| US4548640A (en) | Allylthiodiphenyl ether herbicides | |
| US4755209A (en) | Certain herbicidal 2-pyridyloxy(or phenoxy)-phenoxy-lower alkanoylaminomethylene-phosphonil acids or esters thereof | |
| US4225521A (en) | Herbicidal phosphonates |