CH617570A5 - Herbicidal composition. - Google Patents
Herbicidal composition. Download PDFInfo
- Publication number
- CH617570A5 CH617570A5 CH166876A CH166876A CH617570A5 CH 617570 A5 CH617570 A5 CH 617570A5 CH 166876 A CH166876 A CH 166876A CH 166876 A CH166876 A CH 166876A CH 617570 A5 CH617570 A5 CH 617570A5
- Authority
- CH
- Switzerland
- Prior art keywords
- hydrogen
- oxygen
- phenyl
- lower alkyl
- formula
- Prior art date
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- 230000002363 herbicidal effect Effects 0.000 title claims description 45
- 239000000203 mixture Substances 0.000 title claims description 38
- 150000001875 compounds Chemical class 0.000 claims description 59
- 239000004009 herbicide Substances 0.000 claims description 44
- 229910052739 hydrogen Inorganic materials 0.000 claims description 44
- 239000001257 hydrogen Substances 0.000 claims description 44
- 239000000729 antidote Substances 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 18
- 241000196324 Embryophyta Species 0.000 claims description 16
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- 239000001301 oxygen Substances 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 239000002689 soil Substances 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- -1 nitro, methyl Chemical group 0.000 claims description 11
- 244000038559 crop plants Species 0.000 claims description 10
- 230000000694 effects Effects 0.000 claims description 10
- 125000001188 haloalkyl group Chemical group 0.000 claims description 10
- 238000009331 sowing Methods 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 6
- 230000012010 growth Effects 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 241000894007 species Species 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 208000037824 growth disorder Diseases 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 125000001624 naphthyl group Chemical group 0.000 claims 4
- 230000003042 antagnostic effect Effects 0.000 claims 2
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 230000009931 harmful effect Effects 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 241000209504 Poaceae Species 0.000 claims 1
- 230000002159 abnormal effect Effects 0.000 claims 1
- 150000008061 acetanilides Chemical class 0.000 claims 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 claims 1
- 125000000068 chlorophenyl group Chemical group 0.000 claims 1
- 229940125773 compound 10 Drugs 0.000 claims 1
- 230000003054 hormonal effect Effects 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 claims 1
- 230000036244 malformation Effects 0.000 claims 1
- 125000006501 nitrophenyl group Chemical group 0.000 claims 1
- 239000003223 protective agent Substances 0.000 claims 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 231100000331 toxic Toxicity 0.000 claims 1
- 230000002588 toxic effect Effects 0.000 claims 1
- 150000003918 triazines Chemical class 0.000 claims 1
- 150000003672 ureas Chemical class 0.000 claims 1
- OKUGPJPKMAEJOE-UHFFFAOYSA-N S-propyl dipropylcarbamothioate Chemical compound CCCSC(=O)N(CCC)CCC OKUGPJPKMAEJOE-UHFFFAOYSA-N 0.000 description 74
- GUVLYNGULCJVDO-UHFFFAOYSA-N EPTC Chemical compound CCCN(CCC)C(=O)SCC GUVLYNGULCJVDO-UHFFFAOYSA-N 0.000 description 57
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 54
- 240000008042 Zea mays Species 0.000 description 54
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 53
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 53
- 235000005822 corn Nutrition 0.000 description 53
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- 240000006394 Sorghum bicolor Species 0.000 description 28
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 28
- 240000005979 Hordeum vulgare Species 0.000 description 25
- 235000007340 Hordeum vulgare Nutrition 0.000 description 25
- 235000009430 Thespesia populnea Nutrition 0.000 description 25
- 239000000243 solution Substances 0.000 description 23
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 22
- 238000002360 preparation method Methods 0.000 description 17
- 240000007594 Oryza sativa Species 0.000 description 16
- 235000007164 Oryza sativa Nutrition 0.000 description 16
- 235000009566 rice Nutrition 0.000 description 15
- 239000012074 organic phase Substances 0.000 description 12
- 239000011550 stock solution Substances 0.000 description 12
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 10
- 235000019341 magnesium sulphate Nutrition 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 241000209140 Triticum Species 0.000 description 7
- 235000021307 Triticum Nutrition 0.000 description 7
- FBCCMZVIWNDFMO-UHFFFAOYSA-N dichloroacetyl chloride Chemical compound ClC(Cl)C(Cl)=O FBCCMZVIWNDFMO-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 235000003222 Helianthus annuus Nutrition 0.000 description 6
- 238000007792 addition Methods 0.000 description 6
- 239000008367 deionised water Substances 0.000 description 6
- 229910021641 deionized water Inorganic materials 0.000 description 6
- 230000001681 protective effect Effects 0.000 description 6
- 244000020551 Helianthus annuus Species 0.000 description 5
- 244000062793 Sorghum vulgare Species 0.000 description 5
- 229940075522 antidotes Drugs 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 235000019713 millet Nutrition 0.000 description 4
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 3
- 240000002791 Brassica napus Species 0.000 description 3
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 3
- 244000068988 Glycine max Species 0.000 description 3
- 235000010469 Glycine max Nutrition 0.000 description 3
- 235000021536 Sugar beet Nutrition 0.000 description 3
- XCSGPAVHZFQHGE-UHFFFAOYSA-N alachlor Chemical compound CCC1=CC=CC(CC)=C1N(COC)C(=O)CCl XCSGPAVHZFQHGE-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 235000021186 dishes Nutrition 0.000 description 3
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 description 2
- VEXOEZYUONWVFH-UHFFFAOYSA-N 2-(3-nitrophenyl)-1,3-oxazolidine Chemical compound [O-][N+](=O)C1=CC=CC(C2OCCN2)=C1 VEXOEZYUONWVFH-UHFFFAOYSA-N 0.000 description 2
- 244000058871 Echinochloa crus-galli Species 0.000 description 2
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 2
- JWOLLWQJKQOEOL-UHFFFAOYSA-N OOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOO JWOLLWQJKQOEOL-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 240000003461 Setaria viridis Species 0.000 description 2
- 235000002248 Setaria viridis Nutrition 0.000 description 2
- GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical compound NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 description 2
- HFPGRVHMFSJMOL-UHFFFAOYSA-N dibromomethane Chemical compound Br[CH]Br HFPGRVHMFSJMOL-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 230000002147 killing effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 231100001184 nonphytotoxic Toxicity 0.000 description 2
- 230000008635 plant growth Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- GSJWOQQDBDJRHN-UHFFFAOYSA-N 2,2,4-trimethyl-5-phenyl-1,3-oxazolidine Chemical compound CC1NC(C)(C)OC1C1=CC=CC=C1 GSJWOQQDBDJRHN-UHFFFAOYSA-N 0.000 description 1
- UFXKOCRVIUQSGA-UHFFFAOYSA-N 2,2-dichloro-1-(2,2,4-trimethyl-5-phenyl-1,3-oxazolidin-3-yl)ethanone Chemical compound O1C(C)(C)N(C(=O)C(Cl)Cl)C(C)C1C1=CC=CC=C1 UFXKOCRVIUQSGA-UHFFFAOYSA-N 0.000 description 1
- FWTCEPSLRAJZDH-UHFFFAOYSA-N 2,2-dichloro-1-(2-ethyl-5-phenyl-1,3-oxazolidin-3-yl)ethanone Chemical compound C1N(C(=O)C(Cl)Cl)C(CC)OC1C1=CC=CC=C1 FWTCEPSLRAJZDH-UHFFFAOYSA-N 0.000 description 1
- XVRCBLMVBLQFHM-UHFFFAOYSA-N 2,2-dichloro-1-(2-phenyl-1,3-thiazolidin-3-yl)ethanone Chemical compound ClC(Cl)C(=O)N1CCSC1C1=CC=CC=C1 XVRCBLMVBLQFHM-UHFFFAOYSA-N 0.000 description 1
- GILVSIPQNKPSOV-UHFFFAOYSA-N 2,2-dichloro-1-[2-(3-chlorophenyl)-1,3-thiazolidin-3-yl]ethanone Chemical compound ClC(Cl)C(=O)N1CCSC1C1=CC=CC(Cl)=C1 GILVSIPQNKPSOV-UHFFFAOYSA-N 0.000 description 1
- HWKWYDXHMQQDQJ-UHFFFAOYSA-N 2,3-dibromopropanoyl chloride Chemical compound ClC(=O)C(Br)CBr HWKWYDXHMQQDQJ-UHFFFAOYSA-N 0.000 description 1
- JSTLZWSXHWARBN-UHFFFAOYSA-N 2,5-diphenyl-1,3-oxazolidine Chemical compound C1NC(C=2C=CC=CC=2)OC1C1=CC=CC=C1 JSTLZWSXHWARBN-UHFFFAOYSA-N 0.000 description 1
- OVSKIKFHRZPJSS-DOMIDYPGSA-N 2-(2,4-dichlorophenoxy)acetic acid Chemical compound OC(=O)[14CH2]OC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-DOMIDYPGSA-N 0.000 description 1
- YWDRKJXGWZMFFH-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-1,3-thiazolidine Chemical compound ClC1=CC=CC(Cl)=C1C1SCCN1 YWDRKJXGWZMFFH-UHFFFAOYSA-N 0.000 description 1
- VLJRCRMLQIRLLA-UHFFFAOYSA-N 2-(3-chlorophenyl)-1,3-thiazolidine Chemical compound ClC1=CC=CC(C2SCCN2)=C1 VLJRCRMLQIRLLA-UHFFFAOYSA-N 0.000 description 1
- CCIILNOBNOHYOX-UHFFFAOYSA-N 2-(4-chlorophenyl)-1,3-oxazolidine Chemical compound C1=CC(Cl)=CC=C1C1OCCN1 CCIILNOBNOHYOX-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- GNNBYMVRNDJJRY-UHFFFAOYSA-N 2-ethyl-5-phenyl-1,3-oxazolidine Chemical compound O1C(CC)NCC1C1=CC=CC=C1 GNNBYMVRNDJJRY-UHFFFAOYSA-N 0.000 description 1
- NXOMVTLTYYYYPC-UHFFFAOYSA-N 2-phenyl-1,3-thiazolidine Chemical compound N1CCSC1C1=CC=CC=C1 NXOMVTLTYYYYPC-UHFFFAOYSA-N 0.000 description 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- OWJQTDFFYOQKIX-UHFFFAOYSA-N 3-bromo-1-(5-phenyl-1,3-oxazolidin-3-yl)propan-1-one Chemical compound C1N(C(=O)CCBr)COC1C1=CC=CC=C1 OWJQTDFFYOQKIX-UHFFFAOYSA-N 0.000 description 1
- IHBVNSPHKMCPST-UHFFFAOYSA-N 3-bromopropanoyl chloride Chemical compound ClC(=O)CCBr IHBVNSPHKMCPST-UHFFFAOYSA-N 0.000 description 1
- ZYUWGAVXDLKUKT-UHFFFAOYSA-N 4,4-dimethyl-2-phenyl-1,3-oxazolidine Chemical compound N1C(C)(C)COC1C1=CC=CC=C1 ZYUWGAVXDLKUKT-UHFFFAOYSA-N 0.000 description 1
- HGRPZJNLVMLELR-UHFFFAOYSA-N 5-phenyl-1,3-oxazolidine Chemical compound O1CNCC1C1=CC=CC=C1 HGRPZJNLVMLELR-UHFFFAOYSA-N 0.000 description 1
- MDBGGTQNNUOQRC-UHFFFAOYSA-N Allidochlor Chemical compound ClCC(=O)N(CC=C)CC=C MDBGGTQNNUOQRC-UHFFFAOYSA-N 0.000 description 1
- 240000001592 Amaranthus caudatus Species 0.000 description 1
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 1
- 235000021533 Beta vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- 235000011293 Brassica napus Nutrition 0.000 description 1
- 235000006008 Brassica napus var napus Nutrition 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 244000152970 Digitaria sanguinalis Species 0.000 description 1
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 206010013883 Dwarfism Diseases 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- 241000208818 Helianthus Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- OZBZONOEYUBXTD-UHFFFAOYSA-N OOOOOOOOO Chemical compound OOOOOOOOO OZBZONOEYUBXTD-UHFFFAOYSA-N 0.000 description 1
- UIQWBVPFHHQZHH-UHFFFAOYSA-N OOOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOOO UIQWBVPFHHQZHH-UHFFFAOYSA-N 0.000 description 1
- RRCYYLHJWRYWEI-UHFFFAOYSA-N OOOOOOOOOOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOOOOOOOOOO RRCYYLHJWRYWEI-UHFFFAOYSA-N 0.000 description 1
- 235000015225 Panicum colonum Nutrition 0.000 description 1
- 235000011999 Panicum crusgalli Nutrition 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- 235000006923 Sorghum x drummondii Nutrition 0.000 description 1
- QHTQREMOGMZHJV-UHFFFAOYSA-N Thiobencarb Chemical compound CCN(CC)C(=O)SCC1=CC=C(Cl)C=C1 QHTQREMOGMZHJV-UHFFFAOYSA-N 0.000 description 1
- MWBPRDONLNQCFV-UHFFFAOYSA-N Tri-allate Chemical compound CC(C)N(C(C)C)C(=O)SCC(Cl)=C(Cl)Cl MWBPRDONLNQCFV-UHFFFAOYSA-N 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 235000007244 Zea mays Nutrition 0.000 description 1
- 229960001413 acetanilide Drugs 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 238000009835 boiling Methods 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
- AOJDZKCUAATBGE-UHFFFAOYSA-N bromomethane Chemical compound Br[CH2] AOJDZKCUAATBGE-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000035613 defoliation Effects 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000003815 herbicide antidote Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002576 ketones Chemical class 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
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- NKUXJZGXSINEMP-UHFFFAOYSA-N n-propan-2-yl-1,3,5-triazin-2-amine Chemical compound CC(C)NC1=NC=NC=N1 NKUXJZGXSINEMP-UHFFFAOYSA-N 0.000 description 1
- 150000002927 oxygen compounds Chemical class 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- MFOUDYKPLGXPGO-UHFFFAOYSA-N propachlor Chemical compound ClCC(=O)N(C(C)C)C1=CC=CC=C1 MFOUDYKPLGXPGO-UHFFFAOYSA-N 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 125000001424 substituent group Chemical group 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/04—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/04—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US55006975A | 1975-02-14 | 1975-02-14 | |
| US05/627,986 US4072688A (en) | 1975-02-14 | 1975-11-03 | Haloacyl and thiohaloacyl aryl-substituted oxazolidines and thiazolidines-herbicidal antidotes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH617570A5 true CH617570A5 (en) | 1980-06-13 |
Family
ID=27069322
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH166876A CH617570A5 (en) | 1975-02-14 | 1976-02-11 | Herbicidal composition. |
| CH1105279A CH624554A5 (en) | 1975-02-14 | 1979-12-13 | Method of protecting crops of plants |
| CH1105179A CH619599A5 (en) | 1975-02-14 | 1979-12-13 | Method of protecting crops. |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1105279A CH624554A5 (en) | 1975-02-14 | 1979-12-13 | Method of protecting crops of plants |
| CH1105179A CH619599A5 (en) | 1975-02-14 | 1979-12-13 | Method of protecting crops. |
Country Status (23)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| LU80912A1 (de) * | 1978-02-06 | 1979-06-07 | Nitrokemia Ipartelepek | Unkrautvernichtungsmittel |
| HU178301B (en) * | 1978-02-06 | 1982-04-28 | Nitrokemia Ipartelepek | Herbicide compositions containing naphthaline-carboxylic acid derivatives as antidotes and carbamide derivatives and antidote compositions containing naphthaline-carboxylic acid derivatives |
| US4199506A (en) * | 1978-05-15 | 1980-04-22 | Monsanto Company | 2,4-Disubstituted-5-thiazolecarboxylic acids and derivatives |
| US5225570A (en) * | 1987-08-13 | 1993-07-06 | Monsanto Company | 5-heterocyclic-substituted oxazolidine dihaloacetamides |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1174865A (en) * | 1971-04-16 | 1984-09-25 | Ferenc M. Pallos | Thiolcarbamate herbicides containing nitrogen containing antidote |
| US3989503A (en) * | 1972-10-13 | 1976-11-02 | Stauffer Chemical Company | Herbicidal antidote compositions with substituted oxazolidines and thiazolidines |
| GB1420685A (en) * | 1972-08-15 | 1976-01-07 | Scm Corp | Substituted oxazolidines |
| US3884671A (en) * | 1972-08-15 | 1975-05-20 | Scm Corp | Herbicidal n-haloacyl (2-alkylated) oxazolidines |
| CA1014563A (en) * | 1972-10-13 | 1977-07-26 | Stauffer Chemical Company | Substituted oxazolidines and thiazolidines |
-
1976
- 1976-02-06 BR BR7600775A patent/BR7600775A/pt unknown
- 1976-02-09 HU HU76SA3169A patent/HU181492B/hu unknown
- 1976-02-09 HU HU76SA2884A patent/HU176867B/hu unknown
- 1976-02-09 HU HU76SA3092A patent/HU184694B/hu unknown
- 1976-02-10 TR TR18817A patent/TR18817A/xx unknown
- 1976-02-10 FR FR7603577A patent/FR2309546A1/fr active Granted
- 1976-02-11 CH CH166876A patent/CH617570A5/de not_active IP Right Cessation
- 1976-02-11 EG EG70/76A patent/EG11942A/xx active
- 1976-02-12 GB GB5544/76A patent/GB1484842A/en not_active Expired
- 1976-02-12 DD DD191217A patent/DD122921A5/xx unknown
- 1976-02-12 DE DE19762605586 patent/DE2605586A1/de active Granted
- 1976-02-12 IL IL49023A patent/IL49023A/xx unknown
- 1976-02-12 IT IT48066/76A patent/IT1053846B/it active
- 1976-02-12 SU SU762324802A patent/SU661991A3/ru active
- 1976-02-12 RO RO7684794A patent/RO75509A/ro unknown
- 1976-02-13 DK DK59276*#A patent/DK59276A/da not_active Application Discontinuation
- 1976-02-13 AR AR262257A patent/AR217050A1/es active
- 1976-02-13 JP JP51014787A patent/JPS5259153A/ja active Pending
- 1976-02-13 AU AU11116/76A patent/AU502808B2/en not_active Expired
- 1976-02-13 CA CA245,696A patent/CA1072566A/en not_active Expired
- 1976-02-13 ES ES445173A patent/ES445173A1/es not_active Expired
- 1976-02-13 NL NLAANVRAGE7601500,A patent/NL188577C/xx not_active IP Right Cessation
- 1976-02-14 PL PL1976187228A patent/PL100027B1/pl unknown
-
1977
- 1977-06-27 AR AR268195A patent/AR227500A1/es active
-
1979
- 1979-12-13 CH CH1105279A patent/CH624554A5/de not_active IP Right Cessation
- 1979-12-13 CH CH1105179A patent/CH619599A5/de not_active IP Right Cessation
-
1980
- 1980-04-10 KE KE3041A patent/KE3041A/xx unknown
- 1980-12-30 MY MY229/80A patent/MY8000229A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA1072566A (en) | 1980-02-26 |
| CH619599A5 (en) | 1980-10-15 |
| PL100027B1 (pl) | 1978-08-31 |
| IT1053846B (it) | 1981-10-10 |
| HU181492B (en) | 1983-07-28 |
| DK59276A (da) | 1976-08-15 |
| EG11942A (en) | 1978-03-29 |
| JPS5259153A (en) | 1977-05-16 |
| HU184694B (en) | 1984-09-28 |
| AR217050A1 (es) | 1980-02-29 |
| FR2309546A1 (fr) | 1976-11-26 |
| NL188577C (nl) | 1992-08-03 |
| BR7600775A (pt) | 1977-05-10 |
| MY8000229A (en) | 1980-12-31 |
| FR2309546B1 (enrdf_load_stackoverflow) | 1980-05-16 |
| DD122921A5 (de) | 1976-11-12 |
| CH624554A5 (en) | 1981-08-14 |
| TR18817A (tr) | 1977-11-01 |
| GB1484842A (en) | 1977-09-08 |
| ES445173A1 (es) | 1977-09-16 |
| KE3041A (en) | 1980-04-25 |
| HU176867B (en) | 1981-05-28 |
| DE2605586C2 (enrdf_load_stackoverflow) | 1988-01-14 |
| AR227500A1 (es) | 1982-11-15 |
| DE2605586A1 (de) | 1976-08-26 |
| RO75509A (ro) | 1980-12-30 |
| AU1111676A (en) | 1977-08-18 |
| IL49023A0 (en) | 1976-04-30 |
| NL7601500A (nl) | 1976-08-17 |
| IL49023A (en) | 1979-01-31 |
| AU502808B2 (en) | 1979-08-09 |
| SU661991A3 (ru) | 1979-05-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUE | Assignment |
Owner name: ZENECA INC. |
|
| PL | Patent ceased |