SE458683B - 2-(1-(3-trans-kloroallyloxiamino) propyliden)-5-(2-etyltiopropyl)cyklohexan-1,3-dion och foerenliga salter daerav, herbicida kompositioner innehaallande naemnda foerening, metoder att kontrollera graesartade plantor och graesarter daermed samt metod foer framstaellning daerav - Google Patents
2-(1-(3-trans-kloroallyloxiamino) propyliden)-5-(2-etyltiopropyl)cyklohexan-1,3-dion och foerenliga salter daerav, herbicida kompositioner innehaallande naemnda foerening, metoder att kontrollera graesartade plantor och graesarter daermed samt metod foer framstaellning daeravInfo
- Publication number
- SE458683B SE458683B SE8603868A SE8603868A SE458683B SE 458683 B SE458683 B SE 458683B SE 8603868 A SE8603868 A SE 8603868A SE 8603868 A SE8603868 A SE 8603868A SE 458683 B SE458683 B SE 458683B
- Authority
- SE
- Sweden
- Prior art keywords
- meterode
- weight
- compound according
- compound
- trans
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 23
- 150000003839 salts Chemical class 0.000 title claims description 9
- HJSLFCCWAKVHIW-UHFFFAOYSA-N cyclohexane-1,3-dione Chemical compound O=C1CCCC(=O)C1 HJSLFCCWAKVHIW-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 54
- 230000002363 herbicidal effect Effects 0.000 claims description 25
- 241000196324 Embryophyta Species 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 239000003921 oil Substances 0.000 claims description 12
- 235000019198 oils Nutrition 0.000 claims description 12
- 239000004009 herbicide Substances 0.000 claims description 9
- 239000003960 organic solvent Substances 0.000 claims description 9
- 239000003995 emulsifying agent Substances 0.000 claims description 4
- XGNHRRHYGMFKAQ-OWOJBTEDSA-N o-[(e)-3-chloroprop-2-enyl]hydroxylamine Chemical compound NOC\C=C\Cl XGNHRRHYGMFKAQ-OWOJBTEDSA-N 0.000 claims description 4
- 235000012424 soybean oil Nutrition 0.000 claims description 3
- 239000003549 soybean oil Substances 0.000 claims description 3
- 240000001592 Amaranthus caudatus Species 0.000 claims description 2
- 235000009328 Amaranthus caudatus Nutrition 0.000 claims description 2
- 244000025254 Cannabis sativa Species 0.000 claims description 2
- 244000052363 Cynodon dactylon Species 0.000 claims description 2
- 240000002439 Sorghum halepense Species 0.000 claims description 2
- 240000008042 Zea mays Species 0.000 claims description 2
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 claims description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 2
- 150000001336 alkenes Chemical class 0.000 claims description 2
- 235000009973 maize Nutrition 0.000 claims description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 2
- FBNJCUVUAUBKEN-UHFFFAOYSA-N 5-(2-ethylsulfanylpropyl)-2-propylidenecyclohexane-1,3-dione Chemical compound C(CC)=C1C(CC(CC1=O)CC(C)SCC)=O FBNJCUVUAUBKEN-UHFFFAOYSA-N 0.000 claims 1
- 241000320639 Leptochloa Species 0.000 claims 1
- 241000209094 Oryza Species 0.000 claims 1
- 235000007189 Oryza longistaminata Nutrition 0.000 claims 1
- 240000007594 Oryza sativa Species 0.000 claims 1
- 235000007164 Oryza sativa Nutrition 0.000 claims 1
- 239000005662 Paraffin oil Substances 0.000 claims 1
- 244000171263 Ribes grossularia Species 0.000 claims 1
- 235000002357 Ribes grossularia Nutrition 0.000 claims 1
- 244000202761 Sorghum bicolor subsp verticilliflorum Species 0.000 claims 1
- 241001141210 Urochloa platyphylla Species 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 238000012360 testing method Methods 0.000 description 13
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 231100000674 Phytotoxicity Toxicity 0.000 description 8
- -1 alkali metal alkoxide Chemical class 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 229940125904 compound 1 Drugs 0.000 description 6
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- 239000000969 carrier Substances 0.000 description 5
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000000443 aerosol Substances 0.000 description 4
- ZPFKRQXYKULZKP-UHFFFAOYSA-N butylidene Chemical group [CH2+]CC[CH-] ZPFKRQXYKULZKP-UHFFFAOYSA-N 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
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- 235000007320 Avena fatua Nutrition 0.000 description 3
- 244000075850 Avena orientalis Species 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
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- 239000007858 starting material Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical class N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- IFYAYZHZFQCADV-UHFFFAOYSA-N C(CC)=C1C(C=C(CC1CC(C)SCC)O)=O Chemical compound C(CC)=C1C(C=C(CC1CC(C)SCC)O)=O IFYAYZHZFQCADV-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical class 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 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 241000209504 Poaceae Species 0.000 description 2
- 244000062793 Sorghum vulgare Species 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
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- 235000019713 millet Nutrition 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- OSFBJERFMQCEQY-UHFFFAOYSA-N propylidene Chemical group [CH]CC OSFBJERFMQCEQY-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 239000012085 test solution Substances 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- ZOMGDJFTAMOGOY-UHFFFAOYSA-N 2-(2-ethylsulfanylpropyl)cyclohexane-1,3-dione Chemical compound CCSC(C)CC1C(=O)CCCC1=O ZOMGDJFTAMOGOY-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical class [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 101100298295 Drosophila melanogaster flfl gene Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 244000299507 Gossypium hirsutum Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 240000007049 Juglans regia Species 0.000 description 1
- 235000009496 Juglans regia Nutrition 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical class [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 235000015225 Panicum colonum Nutrition 0.000 description 1
- 244000236458 Panicum colonum Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical class [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 235000008515 Setaria glauca Nutrition 0.000 description 1
- 235000001155 Setaria leucopila Nutrition 0.000 description 1
- 244000010062 Setaria pumila Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical class [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
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- 229910052791 calcium Inorganic materials 0.000 description 1
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- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
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- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Chemical class 0.000 description 1
- IQDXNHZDRQHKEF-UHFFFAOYSA-N dialuminum;dicalcium;dioxido(oxo)silane Chemical compound [Al+3].[Al+3].[Ca+2].[Ca+2].[O-][Si]([O-])=O.[O-][Si]([O-])=O.[O-][Si]([O-])=O.[O-][Si]([O-])=O.[O-][Si]([O-])=O IQDXNHZDRQHKEF-UHFFFAOYSA-N 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
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- 230000012010 growth Effects 0.000 description 1
- 230000007773 growth pattern Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
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- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 230000000877 morphologic effect Effects 0.000 description 1
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- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 229940078499 tricalcium phosphate Drugs 0.000 description 1
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
- C07C251/04—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C251/10—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of an unsaturated carbon skeleton
- C07C251/16—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of an unsaturated carbon skeleton containing six-membered aromatic rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen
- A01N35/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen containing a carbon-to-nitrogen double bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
- C07C251/24—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to carbon atoms of six-membered aromatic rings
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US76830185A | 1985-08-23 | 1985-08-23 | |
| PCT/US1985/001786 WO1987001699A1 (fr) | 1985-08-23 | 1985-09-19 | Herbicides de 2- ad1-(3-chloroallyloxyamino)alkylidene bd-5-alkylthioalkyle-cyclohexane-1,3-dione |
| US79867085A | 1985-11-15 | 1985-11-15 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| SE8603868D0 SE8603868D0 (sv) | 1986-09-15 |
| SE8603868L SE8603868L (sv) | 1987-03-20 |
| SE458683B true SE458683B (sv) | 1989-04-24 |
Family
ID=27118040
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8603868A SE458683B (sv) | 1985-08-23 | 1986-09-15 | 2-(1-(3-trans-kloroallyloxiamino) propyliden)-5-(2-etyltiopropyl)cyklohexan-1,3-dion och foerenliga salter daerav, herbicida kompositioner innehaallande naemnda foerening, metoder att kontrollera graesartade plantor och graesarter daermed samt metod foer framstaellning daerav |
Country Status (14)
| Country | Link |
|---|---|
| EP (1) | EP0236313A1 (fr) |
| KR (1) | KR920010518B1 (fr) |
| CN (2) | CN1021282C (fr) |
| AU (2) | AU586200B2 (fr) |
| BE (1) | BE903349A (fr) |
| CA (1) | CA1271644A (fr) |
| CH (2) | CH666890A5 (fr) |
| DE (1) | DE3627410A1 (fr) |
| FR (1) | FR2586416B1 (fr) |
| GB (2) | GB2188321B (fr) |
| NL (2) | NL193944C (fr) |
| NO (1) | NO162555C (fr) |
| SE (1) | SE458683B (fr) |
| WO (1) | WO1987001699A1 (fr) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU586200B2 (en) * | 1985-08-23 | 1989-07-06 | Arysta Lifescience Corporation | 2-(1-(3-chloroallyloxyamino)alkyl)-5-alkylthioalkyl- cyclohexane-1,3-dione herbicides |
| ES2014493B3 (es) * | 1986-04-24 | 1990-07-16 | Ciba-Geigy Ag | Acil-ciclohexandionas y sus eteres de oximas con efecto herbicida y regulador del crecimiento de las plantas. |
| GB8722838D0 (en) * | 1987-09-29 | 1987-11-04 | Shell Int Research | Oximino ether compounds |
| JP2536075B2 (ja) * | 1988-06-27 | 1996-09-18 | 住友化学工業株式会社 | 除草組成物 |
| US5108488A (en) * | 1989-07-21 | 1992-04-28 | Valent U.S.A. Corporation | Synergistic herbicidal composition |
| US6300281B1 (en) * | 2000-07-03 | 2001-10-09 | Valent U.S.A. Corporation | Optically pure(−) clethodim, compositions and methods for controlling plant growth comprising the same |
| MX2011001869A (es) | 2008-08-19 | 2011-08-15 | Dow Agrosciences Llc | Proceso mejorado para la adicion de tiolatos a compuestos de sulfonilo o carbonilo alfa, beta-insaturados. |
| CN105418470B (zh) * | 2015-11-17 | 2017-12-15 | 江苏长青农化股份有限公司 | 一种烯草酮的合成方法 |
| CN106187841B (zh) * | 2016-07-08 | 2018-01-30 | 山东润博生物科技有限公司 | 一种烯草酮的工业化制备方法 |
| US11503830B2 (en) * | 2019-02-20 | 2022-11-22 | Valent U.S.A., Llc | Clethodim compositions and methods of use thereof |
| CN113024425B (zh) * | 2019-12-24 | 2022-05-17 | 沈阳科创化学品有限公司 | 一种烯草酮的制备方法 |
| CN112225682B (zh) * | 2020-10-19 | 2022-02-25 | 中国科学院大连化学物理研究所 | 一种提高合成烯草酮反应速度的方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4440566A (en) * | 1982-08-05 | 1984-04-03 | Chevron Research Company | Herbicidal substituted 2-(1-(oxyamino)-alkylidene)-cyclohexane-1,3-diones |
| AU556148B2 (en) * | 1982-01-29 | 1986-10-23 | Ici Australia Limited | Cyclohexane -1,3- dione derivatives |
| AU586200B2 (en) * | 1985-08-23 | 1989-07-06 | Arysta Lifescience Corporation | 2-(1-(3-chloroallyloxyamino)alkyl)-5-alkylthioalkyl- cyclohexane-1,3-dione herbicides |
-
1985
- 1985-09-19 AU AU49541/85A patent/AU586200B2/en not_active Expired
- 1985-09-19 EP EP85904913A patent/EP0236313A1/fr active Pending
- 1985-09-19 WO PCT/US1985/001786 patent/WO1987001699A1/fr not_active Ceased
- 1985-09-19 CH CH1974/87A patent/CH666890A5/de not_active IP Right Cessation
- 1985-09-19 KR KR1019860700645A patent/KR920010518B1/ko not_active Expired
- 1985-09-19 NL NL8520309A patent/NL193944C/nl not_active IP Right Cessation
- 1985-09-19 GB GB8708127A patent/GB2188321B/en not_active Expired
- 1985-09-30 BE BE0/215661A patent/BE903349A/fr not_active IP Right Cessation
-
1986
- 1986-06-30 AU AU59380/86A patent/AU585999B2/en not_active Ceased
- 1986-07-22 NL NL8601900A patent/NL8601900A/nl not_active Application Discontinuation
- 1986-07-30 CN CN90107624A patent/CN1021282C/zh not_active Expired - Lifetime
- 1986-07-30 CN CN86105662A patent/CN1011782B/zh not_active Expired
- 1986-08-13 DE DE19863627410 patent/DE3627410A1/de not_active Withdrawn
- 1986-08-18 FR FR8611806A patent/FR2586416B1/fr not_active Expired
- 1986-08-19 CH CH3344/86A patent/CH667086A5/de not_active IP Right Cessation
- 1986-08-20 CA CA000516351A patent/CA1271644A/fr not_active Expired - Fee Related
- 1986-08-21 GB GB8620373A patent/GB2179352B/en not_active Expired
- 1986-09-15 SE SE8603868A patent/SE458683B/sv not_active IP Right Cessation
- 1986-09-18 NO NO86863733A patent/NO162555C/no not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CH667086A5 (de) | 1988-09-15 |
| CH666890A5 (de) | 1988-08-31 |
| KR870700287A (ko) | 1987-12-28 |
| CN1051285A (zh) | 1991-05-15 |
| AU5938086A (en) | 1987-02-26 |
| NL8520309A (nl) | 1985-09-19 |
| AU586200B2 (en) | 1989-07-06 |
| AU585999B2 (en) | 1989-06-29 |
| GB2179352B (en) | 1989-08-09 |
| NO863733D0 (no) | 1986-09-18 |
| FR2586416A1 (fr) | 1987-02-27 |
| GB8620373D0 (en) | 1986-10-01 |
| DE3627410A1 (de) | 1987-02-26 |
| BE903349A (fr) | 1986-04-01 |
| GB8708127D0 (en) | 1987-05-13 |
| EP0236313A1 (fr) | 1987-09-16 |
| WO1987001699A1 (fr) | 1987-03-26 |
| NO162555B (no) | 1989-10-09 |
| GB2188321B (en) | 1989-08-31 |
| NL193944B (nl) | 2000-11-01 |
| CN1021282C (zh) | 1993-06-23 |
| NO863733L (no) | 1987-03-26 |
| AU4954185A (en) | 1987-04-07 |
| GB2188321A (en) | 1987-09-30 |
| CN86105662A (zh) | 1987-04-08 |
| NO162555C (no) | 1990-01-17 |
| GB2179352A (en) | 1987-03-04 |
| KR920010518B1 (ko) | 1992-12-04 |
| NL8601900A (nl) | 1987-03-16 |
| SE8603868L (sv) | 1987-03-20 |
| NL193944C (nl) | 2001-03-02 |
| SE8603868D0 (sv) | 1986-09-15 |
| FR2586416B1 (fr) | 1989-06-02 |
| CA1271644A (fr) | 1990-07-17 |
| CN1011782B (zh) | 1991-02-27 |
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