DK141441B - Substituerede oxazolidiner og thiazolidiner til anvendelse som modgift mod herbicider. - Google Patents
Substituerede oxazolidiner og thiazolidiner til anvendelse som modgift mod herbicider. Download PDFInfo
- Publication number
- DK141441B DK141441B DK549073A DK549073A DK141441B DK 141441 B DK141441 B DK 141441B DK 549073 A DK549073 A DK 549073A DK 549073 A DK549073 A DK 549073A DK 141441 B DK141441 B DK 141441B
- Authority
- DK
- Denmark
- Prior art keywords
- weeks
- corn
- barley
- rice
- rape
- Prior art date
Links
- 239000004009 herbicide Substances 0.000 title description 37
- 239000000729 antidote Substances 0.000 title description 20
- 229940075522 antidotes Drugs 0.000 title description 8
- 150000002917 oxazolidines Chemical class 0.000 title description 4
- 150000003548 thiazolidines Chemical class 0.000 title description 4
- 240000008042 Zea mays Species 0.000 description 64
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 63
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 63
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 56
- 235000005822 corn Nutrition 0.000 description 56
- 240000005979 Hordeum vulgare Species 0.000 description 52
- 235000007340 Hordeum vulgare Nutrition 0.000 description 52
- 150000001875 compounds Chemical class 0.000 description 41
- 240000007594 Oryza sativa Species 0.000 description 35
- 235000007164 Oryza sativa Nutrition 0.000 description 34
- 235000009566 rice Nutrition 0.000 description 33
- 230000002363 herbicidal effect Effects 0.000 description 29
- 239000002689 soil Substances 0.000 description 28
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- 235000003222 Helianthus annuus Nutrition 0.000 description 21
- 241000208818 Helianthus Species 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- GUVLYNGULCJVDO-UHFFFAOYSA-N EPTC Chemical compound CCCN(CCC)C(=O)SCC GUVLYNGULCJVDO-UHFFFAOYSA-N 0.000 description 17
- -1 1,1-dimethylbutyl Chemical group 0.000 description 15
- 241000196324 Embryophyta Species 0.000 description 13
- 238000002360 preparation method Methods 0.000 description 11
- 240000006394 Sorghum bicolor Species 0.000 description 10
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 244000068988 Glycine max Species 0.000 description 7
- 235000010469 Glycine max Nutrition 0.000 description 7
- 241000209140 Triticum Species 0.000 description 7
- 235000021307 Triticum Nutrition 0.000 description 7
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 7
- 235000009973 maize Nutrition 0.000 description 7
- 238000009331 sowing Methods 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 239000011550 stock solution Substances 0.000 description 7
- 238000011282 treatment Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 244000075850 Avena orientalis Species 0.000 description 5
- 235000007319 Avena orientalis Nutrition 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 240000002791 Brassica napus Species 0.000 description 4
- 240000001931 Ludwigia octovalvis Species 0.000 description 4
- 230000009471 action Effects 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 4
- 244000038559 crop plants Species 0.000 description 4
- 230000012010 growth Effects 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 4
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 3
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 244000299507 Gossypium hirsutum Species 0.000 description 3
- 235000021536 Sugar beet Nutrition 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 230000008635 plant growth Effects 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 241000894007 species Species 0.000 description 3
- VSHIRTNKIXRXMI-UHFFFAOYSA-N 2,2-dimethyl-1,3-oxazolidine Chemical compound CC1(C)NCCO1 VSHIRTNKIXRXMI-UHFFFAOYSA-N 0.000 description 2
- SNPQRYOQWLOTFA-UHFFFAOYSA-N 2,2-dimethyl-1,3-thiazolidine Chemical compound CC1(C)NCCS1 SNPQRYOQWLOTFA-UHFFFAOYSA-N 0.000 description 2
- UENGBOCGGKLVJJ-UHFFFAOYSA-N 2-chloro-1-(2,4-difluorophenyl)ethanone Chemical compound FC1=CC=C(C(=O)CCl)C(F)=C1 UENGBOCGGKLVJJ-UHFFFAOYSA-N 0.000 description 2
- KUGRPPRAQNPSQD-UHFFFAOYSA-N OOOOO Chemical compound OOOOO KUGRPPRAQNPSQD-UHFFFAOYSA-N 0.000 description 2
- RTYZCUMXOXNVSI-UHFFFAOYSA-N OOOOOOOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOOOOOOO RTYZCUMXOXNVSI-UHFFFAOYSA-N 0.000 description 2
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 2
- 241000209504 Poaceae Species 0.000 description 2
- GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical compound NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 2
- 230000003042 antagnostic effect Effects 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 239000004568 cement Substances 0.000 description 2
- 230000002089 crippling effect Effects 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- FBCCMZVIWNDFMO-UHFFFAOYSA-N dichloroacetyl chloride Chemical compound ClC(Cl)C(Cl)=O FBCCMZVIWNDFMO-UHFFFAOYSA-N 0.000 description 2
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 239000003815 herbicide antidote Substances 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 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
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000002574 poison Substances 0.000 description 2
- 231100000614 poison Toxicity 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000011814 protection agent Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 2
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical group CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 description 1
- XMPCGZCCOXWBKR-UHFFFAOYSA-N 2,2,5-trimethyl-1,3-oxazolidine Chemical compound CC1CNC(C)(C)O1 XMPCGZCCOXWBKR-UHFFFAOYSA-N 0.000 description 1
- LQBBYHUQQRZRLK-UHFFFAOYSA-N 2,2-dibromoacetyl chloride Chemical compound ClC(=O)C(Br)Br LQBBYHUQQRZRLK-UHFFFAOYSA-N 0.000 description 1
- HLNYFFJCUFOZHS-UHFFFAOYSA-N 2,2-dichloro-1-(2,2,5-trimethyl-1,3-oxazolidin-5-yl)ethanone Chemical compound CC1(OC(CN1)(C(C(Cl)Cl)=O)C)C HLNYFFJCUFOZHS-UHFFFAOYSA-N 0.000 description 1
- CYXOSCYHMWJFQY-UHFFFAOYSA-N 2,2-dichloro-1-(2,2-dimethyl-1,3-thiazolidin-5-yl)ethanone Chemical compound CC1(SC(CN1)C(C(Cl)Cl)=O)C CYXOSCYHMWJFQY-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
- 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
- AVJIQBUUPACBPG-UHFFFAOYSA-N 2-ethyl-1,3-oxazolidine Chemical compound CCC1NCCO1 AVJIQBUUPACBPG-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
- 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 1
- XZIIFPSPUDAGJM-UHFFFAOYSA-N 6-chloro-2-n,2-n-diethylpyrimidine-2,4-diamine Chemical compound CCN(CC)C1=NC(N)=CC(Cl)=N1 XZIIFPSPUDAGJM-UHFFFAOYSA-N 0.000 description 1
- 241001621841 Alopecurus myosuroides Species 0.000 description 1
- 235000009393 Avena byzantina Nutrition 0.000 description 1
- 235000011293 Brassica napus Nutrition 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 241000521088 Coua Species 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 235000009429 Gossypium barbadense Nutrition 0.000 description 1
- 235000009432 Gossypium hirsutum Nutrition 0.000 description 1
- 244000020551 Helianthus annuus Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- UIQWBVPFHHQZHH-UHFFFAOYSA-N OOOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOOO UIQWBVPFHHQZHH-UHFFFAOYSA-N 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- 241000364051 Pima Species 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 235000009430 Thespesia populnea Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 150000008061 acetanilides Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000003619 algicide Substances 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 239000000022 bacteriostatic agent Substances 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- UCVODTZQZHMTPN-UHFFFAOYSA-N heptanoyl chloride Chemical compound CCCCCCC(Cl)=O UCVODTZQZHMTPN-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 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
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000002262 irrigation Effects 0.000 description 1
- 238000003973 irrigation Methods 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
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 230000000051 modifying effect Effects 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 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
- 231100001183 nonphototoxic Toxicity 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- QCMHWZUFWLOOGI-UHFFFAOYSA-N s-ethyl chloromethanethioate Chemical compound CCSC(Cl)=O QCMHWZUFWLOOGI-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229940035044 sorbitan monolaurate Drugs 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910052717 sulfur Chemical group 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 239000004557 technical material Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 235000018322 upland cotton Nutrition 0.000 description 1
- 238000010626 work up procedure Methods 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
- 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
- C07D263/06—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 with hydrocarbon radicals, substituted by oxygen atoms, attached to ring carbon atoms
-
- 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)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US29758272A | 1972-10-13 | 1972-10-13 | |
| US29758272 | 1972-10-13 | ||
| US35654873A | 1973-05-02 | 1973-05-02 | |
| US35654873 | 1973-05-02 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DK141441B true DK141441B (da) | 1980-03-17 |
| DK141441C DK141441C (enrdf_load_stackoverflow) | 1980-10-13 |
Family
ID=26970223
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK549073A DK141441B (da) | 1972-10-13 | 1973-10-10 | Substituerede oxazolidiner og thiazolidiner til anvendelse som modgift mod herbicider. |
Country Status (7)
| Country | Link |
|---|---|
| BG (1) | BG24540A3 (enrdf_load_stackoverflow) |
| CA (1) | CA1014563A (enrdf_load_stackoverflow) |
| CS (1) | CS197227B2 (enrdf_load_stackoverflow) |
| DE (1) | DE2350547C2 (enrdf_load_stackoverflow) |
| DK (1) | DK141441B (enrdf_load_stackoverflow) |
| NL (1) | NL178789C (enrdf_load_stackoverflow) |
| PH (1) | PH13508A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK156807B (da) * | 1978-02-06 | 1989-10-09 | Nitrokemia Ipartelepek | Antagonist til beskyttelse af kulturplanter mod den beskadigende virkning af herbicidt virksomme forbindelser samt deres anvendelse |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3989503A (en) * | 1972-10-13 | 1976-11-02 | Stauffer Chemical Company | Herbicidal antidote compositions with substituted oxazolidines and thiazolidines |
| US4186130A (en) * | 1973-05-02 | 1980-01-29 | Stauffer Chemical Company | N-(haloalkanoyl) oxazolidines |
| BR7600775A (pt) * | 1975-02-14 | 1977-05-10 | Stauffer Chemical Co | Processo para a obtencao de(tio)haloacil-(tia)oxazolidinas arisubstituidas e composicoes herbicidas sinergeticas que as contem |
| US4268677A (en) * | 1976-02-06 | 1981-05-19 | Stauffer Chemical Company | Substituted oxazolidines and thiazolidines |
| US4236011A (en) * | 1979-06-18 | 1980-11-25 | Stauffer Chemical Company | N-Acyl oxazolidines and thiazolidines as herbicides |
| IT1196507B (it) * | 1986-07-16 | 1988-11-16 | Oxon Italia Spa | 5-imminometil-aloacilossazolidone ad azione inibitrice della fitotossicita' di erbicidi |
| US4938796A (en) * | 1987-07-06 | 1990-07-03 | Ici Americas Inc. | Herbicidal compositions of acylated 1,3-dicarbonyl herbicides and antidotes therefor |
| DE10326386A1 (de) | 2003-06-12 | 2004-12-30 | Bayer Cropscience Ag | N-Heterocyclyl-phenylsubstituierte cyclische Ketoenole |
| DE10331675A1 (de) | 2003-07-14 | 2005-02-10 | Bayer Cropscience Ag | Hetarylsubstituierte Pyrazolidindion-Derivate |
| DE10337496A1 (de) | 2003-08-14 | 2005-04-14 | Bayer Cropscience Ag | 4-Biphenylsubstituierte-4-substituierte-pyrazolidin-3,5-dione |
| DE10337497A1 (de) | 2003-08-14 | 2005-03-10 | Bayer Cropscience Ag | 4-Biphenylsubstituierte-Pyrazolidin-3,5-dion-Derivate |
| DE10354629A1 (de) | 2003-11-22 | 2005-06-30 | Bayer Cropscience Ag | 2-Ethyl-4,6-dimethyl-phenyl substituierte spirocyclische Tetramsäure-Derivate |
| DE10354628A1 (de) | 2003-11-22 | 2005-06-16 | Bayer Cropscience Ag | 2-Ethyl-4,6-dimethyl-phenyl-substituierte Tetramsäure-Derivate |
| DE102004014620A1 (de) | 2004-03-25 | 2005-10-06 | Bayer Cropscience Ag | 2,4,6-phenylsubstituierte cyclische Ketoenole |
| DE102004030753A1 (de) | 2004-06-25 | 2006-01-19 | Bayer Cropscience Ag | 3'-Alkoxy spirocyclische Tetram- und Tretronsäuren |
| DE102004035134A1 (de) | 2004-07-20 | 2006-02-16 | Bayer Cropscience Ag | Selektive Insektizide auf Basis von Halogenalkylnicotinsäurederivaten, Anthranilsäureamiden oder Phthalsäurediamiden und Safenern |
| DE102004044827A1 (de) | 2004-09-16 | 2006-03-23 | Bayer Cropscience Ag | Jod-phenylsubstituierte cyclische Ketoenole |
| DE102004053191A1 (de) | 2004-11-04 | 2006-05-11 | Bayer Cropscience Ag | 2,6-Diethyl-4-methyl-phenyl substituierte Tetramsäure-Derivate |
| DE102004053192A1 (de) | 2004-11-04 | 2006-05-11 | Bayer Cropscience Ag | 2-Alkoxy-6-alkyl-phenyl substituierte spirocyclische Tetramsäure-Derivate |
| DE102005059891A1 (de) | 2005-12-15 | 2007-06-28 | Bayer Cropscience Ag | 3'-Alkoxy-spirocyclopentyl substituierte Tetram- und Tetronsäuren |
| DE102006007882A1 (de) | 2006-02-21 | 2007-08-30 | Bayer Cropscience Ag | Cycloalkyl-phenylsubstituierte cyclische Ketoenole |
| DE102006025874A1 (de) | 2006-06-02 | 2007-12-06 | Bayer Cropscience Ag | Alkoxyalkyl-substituierte cyclische Ketoenole |
| DE102006050148A1 (de) | 2006-10-25 | 2008-04-30 | Bayer Cropscience Ag | Trifluormethoxy-phenylsubstituierte Tetramsäure-Derivate |
| DE102006057037A1 (de) | 2006-12-04 | 2008-06-05 | Bayer Cropscience Ag | cis-Alkoxyspirocyclische biphenylsubstituierte Tetramsäure-Derivate |
| DE102006057036A1 (de) | 2006-12-04 | 2008-06-05 | Bayer Cropscience Ag | Biphenylsubstituierte spirocyclische Ketoenole |
| EP2020413A1 (de) | 2007-08-02 | 2009-02-04 | Bayer CropScience AG | Oxaspirocyclische-spiro-substituierte Tetram- und Tetronsäure-Derivate |
| EP2045240A1 (de) | 2007-09-25 | 2009-04-08 | Bayer CropScience AG | Halogenalkoxyspirocyclische Tetram- und Tetronsäure-Derivate |
| EP2103615A1 (de) | 2008-03-19 | 2009-09-23 | Bayer CropScience AG | 4'4'-Dioxaspiro-spirocyclisch substituierte Tetramate |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1670548A1 (de) * | 1967-02-04 | 1971-02-11 | Dynamit Nobel Ag | Verfahren zur Herstellung von N-Acyloxazolidinen |
| DE1670557A1 (de) * | 1967-03-21 | 1971-07-01 | Dynamit Nobel Ag | Verfahren zur Herstellung von 2-substituierten N-Acyloxazolidinen |
-
1973
- 1973-09-27 CA CA182,035A patent/CA1014563A/en not_active Expired
- 1973-10-05 PH PH15094A patent/PH13508A/en unknown
- 1973-10-09 DE DE19732350547 patent/DE2350547C2/de not_active Expired
- 1973-10-10 DK DK549073A patent/DK141441B/da not_active IP Right Cessation
- 1973-10-12 NL NL7314090A patent/NL178789C/xx not_active IP Right Cessation
- 1973-10-12 CS CS705473A patent/CS197227B2/cs unknown
- 1973-10-13 BG BG024738A patent/BG24540A3/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK156807B (da) * | 1978-02-06 | 1989-10-09 | Nitrokemia Ipartelepek | Antagonist til beskyttelse af kulturplanter mod den beskadigende virkning af herbicidt virksomme forbindelser samt deres anvendelse |
Also Published As
| Publication number | Publication date |
|---|---|
| PH13508A (en) | 1980-06-03 |
| DK141441C (enrdf_load_stackoverflow) | 1980-10-13 |
| DE2350547A1 (de) | 1974-04-25 |
| CA1014563A (en) | 1977-07-26 |
| CS197227B2 (en) | 1980-04-30 |
| DE2350547C2 (de) | 1986-10-23 |
| NL178789C (nl) | 1986-05-16 |
| NL178789B (nl) | 1985-12-16 |
| NL7314090A (enrdf_load_stackoverflow) | 1974-04-16 |
| BG24540A3 (en) | 1978-03-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DK141441B (da) | Substituerede oxazolidiner og thiazolidiner til anvendelse som modgift mod herbicider. | |
| US4186130A (en) | N-(haloalkanoyl) oxazolidines | |
| US3959304A (en) | Certain 3-haloacyl-2,2,5-trimethyl-oxazolidines | |
| DK146142B (da) | Herbicidt middel indeholdende et thiocarbamat | |
| US4115095A (en) | 5-Aryl-1,2,4-thiadiazole-3-carboxylates and agricultural methods | |
| PL102610B1 (pl) | Srodek chwastobojczy | |
| HU184615B (en) | Compositions with antidote activity and process for preparing oxime derivatives applied as active substances thereof | |
| US4243811A (en) | 2,2,4-Trimethyl-4-hydroxymethyl-3-dichloroacetyl oxazolidine | |
| US3976469A (en) | Halogenated ketones as herbicide antidotes | |
| JPS6116395B2 (enrdf_load_stackoverflow) | ||
| US4036628A (en) | Phosphorus containing herbicide antidotes | |
| US4321084A (en) | Certain halogenated phenols as antidotes for thiocarbamate herbicides | |
| US4531966A (en) | Herbicide compositions | |
| US4236011A (en) | N-Acyl oxazolidines and thiazolidines as herbicides | |
| US4021228A (en) | Sulfide herbicide antidote compositions and method of use | |
| US4319031A (en) | Substituted thiazolidines | |
| US4488897A (en) | Dichloromethyl oxadiazole herbicide antidotes | |
| CS243494B2 (en) | Antidoteing agent for cultural plants protection against damage by herbicides of thiocarbamate-type and acetanilide-type | |
| NO167335B (no) | Signalinnretning for industriell oppmaaling. | |
| US3996043A (en) | Triazine--antidote compositions and methods of use for cotton | |
| PL94157B1 (en) | Sulfoxide and sulfone thiazolidines, compositions thereof and their utility as herbicide antidotes[US4137066A] | |
| EP0068709B1 (en) | Herbicide antidotes, production, use and compositions thereof | |
| US4268677A (en) | Substituted oxazolidines and thiazolidines | |
| US4089673A (en) | Halogenated ketones as herbicide antidotes | |
| US4030911A (en) | Sulfide herbicide antidote compositions and method of use |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUP | Patent expired |