DE2609204A1 - 2-sulfinyl-und 2-sulfonylpyridin- n-oxid-verbindungen - Google Patents
2-sulfinyl-und 2-sulfonylpyridin- n-oxid-verbindungenInfo
- Publication number
- DE2609204A1 DE2609204A1 DE19762609204 DE2609204A DE2609204A1 DE 2609204 A1 DE2609204 A1 DE 2609204A1 DE 19762609204 DE19762609204 DE 19762609204 DE 2609204 A DE2609204 A DE 2609204A DE 2609204 A1 DE2609204 A1 DE 2609204A1
- Authority
- DE
- Germany
- Prior art keywords
- oxide
- pyridine
- phenyl
- compound
- hydrogen
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- WANCMADGLFGMEC-UHFFFAOYSA-N 1-hydroxy-2-sulfonylpyridine Chemical class ON1C=CC=CC1=S(=O)=O WANCMADGLFGMEC-UHFFFAOYSA-N 0.000 title claims description 8
- -1 analog Chemical group 0.000 claims description 78
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 claims description 40
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 37
- 241000196324 Embryophyta Species 0.000 claims description 33
- 150000001875 compounds Chemical class 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 17
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 229960000583 acetic acid Drugs 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 239000007800 oxidant agent Substances 0.000 claims description 6
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 5
- 239000012362 glacial acetic acid Substances 0.000 claims description 5
- 239000012876 carrier material Substances 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- FWZSSYLZVKVKIH-UHFFFAOYSA-N 1-oxido-2-(1-phenylethylsulfonyl)pyridin-1-ium Chemical compound C=1C=CC=[N+]([O-])C=1S(=O)(=O)C(C)C1=CC=CC=C1 FWZSSYLZVKVKIH-UHFFFAOYSA-N 0.000 claims description 2
- OFBBTMAIGSUJAS-UHFFFAOYSA-N 2-[(2,6-dichlorophenyl)methylsulfonyl]-1-oxidopyridin-1-ium Chemical compound [O-][N+]1=CC=CC=C1S(=O)(=O)CC1=C(Cl)C=CC=C1Cl OFBBTMAIGSUJAS-UHFFFAOYSA-N 0.000 claims description 2
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
- 150000002751 molybdenum Chemical class 0.000 claims description 2
- 239000012454 non-polar solvent Substances 0.000 claims description 2
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000005504 styryl group Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 2
- 229910052721 tungsten Inorganic materials 0.000 claims description 2
- 239000010937 tungsten Substances 0.000 claims description 2
- 229910052720 vanadium Inorganic materials 0.000 claims description 2
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 claims description 2
- 229910052726 zirconium Inorganic materials 0.000 claims description 2
- ZHZZQAASGHFAQS-UHFFFAOYSA-N 1-oxido-2-[(2,4,6-trimethylphenyl)methylsulfonyl]pyridin-1-ium Chemical compound CC1=CC(C)=CC(C)=C1CS(=O)(=O)C1=CC=CC=[N+]1[O-] ZHZZQAASGHFAQS-UHFFFAOYSA-N 0.000 claims 1
- 241001669680 Dormitator maculatus Species 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 150000002500 ions Chemical class 0.000 claims 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 32
- 239000000126 substance Substances 0.000 description 32
- 238000002844 melting Methods 0.000 description 30
- 230000008018 melting Effects 0.000 description 30
- 239000000243 solution Substances 0.000 description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- 230000002363 herbicidal effect Effects 0.000 description 21
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- 239000002689 soil Substances 0.000 description 14
- 239000004009 herbicide Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 11
- 159000000000 sodium salts Chemical class 0.000 description 11
- 244000025254 Cannabis sativa Species 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 244000062793 Sorghum vulgare Species 0.000 description 9
- 235000019713 millet Nutrition 0.000 description 9
- 150000003462 sulfoxides Chemical class 0.000 description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
- 150000003457 sulfones Chemical class 0.000 description 8
- 244000105624 Arachis hypogaea Species 0.000 description 7
- 244000068988 Glycine max Species 0.000 description 7
- 235000010469 Glycine max Nutrition 0.000 description 7
- 150000001204 N-oxides Chemical class 0.000 description 7
- 240000001592 Amaranthus caudatus Species 0.000 description 6
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YBBJKCMMCRQZMA-UHFFFAOYSA-N pyrithione Chemical compound ON1C=CC=CC1=S YBBJKCMMCRQZMA-UHFFFAOYSA-N 0.000 description 6
- 240000006240 Linum usitatissimum Species 0.000 description 5
- 235000004431 Linum usitatissimum Nutrition 0.000 description 5
- 244000234609 Portulaca oleracea Species 0.000 description 5
- 235000001855 Portulaca oleracea Nutrition 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 238000013459 approach Methods 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000013067 intermediate product Substances 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 244000075850 Avena orientalis Species 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 4
- 244000078127 Eleusine coracana Species 0.000 description 4
- 235000013499 Eleusine coracana subsp coracana Nutrition 0.000 description 4
- 241000219146 Gossypium Species 0.000 description 4
- 241000227653 Lycopersicon Species 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229960003750 ethyl chloride Drugs 0.000 description 4
- 235000020232 peanut Nutrition 0.000 description 4
- 150000002978 peroxides Chemical class 0.000 description 4
- 235000010777 Arachis hypogaea Nutrition 0.000 description 3
- 235000007319 Avena orientalis Nutrition 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 240000008853 Datura stramonium Species 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241000287828 Gallus gallus Species 0.000 description 3
- 240000004658 Medicago sativa Species 0.000 description 3
- 244000061176 Nicotiana tabacum Species 0.000 description 3
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000004495 emulsifiable concentrate Substances 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 239000004563 wettable powder Substances 0.000 description 3
- LBOBESSDSGODDD-UHFFFAOYSA-N 1,3-dichloro-2-(chloromethyl)benzene Chemical compound ClCC1=C(Cl)C=CC=C1Cl LBOBESSDSGODDD-UHFFFAOYSA-N 0.000 description 2
- LJEPNISDEZZFJI-UHFFFAOYSA-N 1-oxido-2-[(2,3,6-trimethylphenyl)methylsulfinyl]pyridin-1-ium Chemical compound CC1=CC=C(C)C(CS(=O)C=2[N+](=CC=CC=2)[O-])=C1C LJEPNISDEZZFJI-UHFFFAOYSA-N 0.000 description 2
- ODBZRVDFVMOCMZ-UHFFFAOYSA-N 2-[(2,5-dimethylphenyl)methylsulfonyl]-1-oxidopyridin-1-ium Chemical compound CC1=CC=C(C)C(CS(=O)(=O)C=2[N+](=CC=CC=2)[O-])=C1 ODBZRVDFVMOCMZ-UHFFFAOYSA-N 0.000 description 2
- HRWUFIUAEIXBHL-UHFFFAOYSA-N 2-[(2,6-dichlorophenyl)methylsulfanyl]-1-oxidopyridin-1-ium Chemical compound [O-][N+]1=CC=CC=C1SCC1=C(Cl)C=CC=C1Cl HRWUFIUAEIXBHL-UHFFFAOYSA-N 0.000 description 2
- QWMFKVNJIYNWII-UHFFFAOYSA-N 5-bromo-2-(2,5-dimethylpyrrol-1-yl)pyridine Chemical compound CC1=CC=C(C)N1C1=CC=C(Br)C=N1 QWMFKVNJIYNWII-UHFFFAOYSA-N 0.000 description 2
- 235000005474 African couch grass Nutrition 0.000 description 2
- 244000237956 Amaranthus retroflexus Species 0.000 description 2
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 235000007320 Avena fatua Nutrition 0.000 description 2
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 235000002262 Lycopersicon Nutrition 0.000 description 2
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- 241000209117 Panicum Species 0.000 description 2
- 235000011999 Panicum crusgalli Nutrition 0.000 description 2
- 235000006443 Panicum miliaceum subsp. miliaceum Nutrition 0.000 description 2
- 235000009037 Panicum miliaceum subsp. ruderale Nutrition 0.000 description 2
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- 240000003461 Setaria viridis Species 0.000 description 2
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- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
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- 150000004820 halides Chemical class 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229920000056 polyoxyethylene ether Polymers 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 244000045561 useful plants Species 0.000 description 2
- HOLOJLLLDKVVJY-UHFFFAOYSA-N 1,2,4-trichloro-3-(chloromethyl)benzene Chemical compound ClCC1=C(Cl)C=CC(Cl)=C1Cl HOLOJLLLDKVVJY-UHFFFAOYSA-N 0.000 description 1
- OZZJBUFLHMQBFN-UHFFFAOYSA-N 1-oxido-2-(1-phenylbutylsulfonyl)pyridin-1-ium Chemical compound C=1C=CC=[N+]([O-])C=1S(=O)(=O)C(CCC)C1=CC=CC=C1 OZZJBUFLHMQBFN-UHFFFAOYSA-N 0.000 description 1
- KCWZUIVGUKHLIQ-UHFFFAOYSA-N 1-oxido-2-(2-phenylethylsulfinyl)pyridin-1-ium Chemical compound [O-][N+]1=CC=CC=C1S(=O)CCC1=CC=CC=C1 KCWZUIVGUKHLIQ-UHFFFAOYSA-N 0.000 description 1
- BSBYBBFFYJHYON-UHFFFAOYSA-N 1-oxido-2-[(2,3,4,5,6-pentachlorophenyl)methylsulfonyl]pyridin-1-ium Chemical compound [O-][N+]1=CC=CC=C1S(=O)(=O)CC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl BSBYBBFFYJHYON-UHFFFAOYSA-N 0.000 description 1
- PVTSJKNFUUEWGQ-UHFFFAOYSA-N 1-oxido-2-[(2,3,6-trichlorophenyl)methylsulfanyl]pyridin-1-ium Chemical compound [O-][N+]1=CC=CC=C1SCC1=C(Cl)C=CC(Cl)=C1Cl PVTSJKNFUUEWGQ-UHFFFAOYSA-N 0.000 description 1
- FITRQQNWYVGGEZ-UHFFFAOYSA-N 1-oxido-2-[(2,3,6-trichlorophenyl)methylsulfonyl]pyridin-1-ium Chemical compound [O-][N+]1=CC=CC=C1S(=O)(=O)CC1=C(Cl)C=CC(Cl)=C1Cl FITRQQNWYVGGEZ-UHFFFAOYSA-N 0.000 description 1
- PQTUUJQMBFSAFH-UHFFFAOYSA-N 2-(1-chloroethyl)naphthalene Chemical compound C1=CC=CC2=CC(C(Cl)C)=CC=C21 PQTUUJQMBFSAFH-UHFFFAOYSA-N 0.000 description 1
- PECXPZGFZFGDRD-UHFFFAOYSA-N 2-(chloromethyl)-1,4-dimethylbenzene Chemical compound CC1=CC=C(C)C(CCl)=C1 PECXPZGFZFGDRD-UHFFFAOYSA-N 0.000 description 1
- FOHDZNPIEIRSGF-UHFFFAOYSA-N 2-(cyclohexylmethylsulfonyl)-1-oxidopyridin-1-ium Chemical compound [O-][N+]1=CC=CC=C1S(=O)(=O)CC1CCCCC1 FOHDZNPIEIRSGF-UHFFFAOYSA-N 0.000 description 1
- PLTMGCBIYRHOEK-UHFFFAOYSA-N 2-(naphthalen-1-ylmethylsulfonyl)-1-oxidopyridin-1-ium Chemical compound [O-][N+]1=CC=CC=C1S(=O)(=O)CC1=CC=CC2=CC=CC=C12 PLTMGCBIYRHOEK-UHFFFAOYSA-N 0.000 description 1
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- DTCNNZIBPORQFK-UHFFFAOYSA-N 2-[(2,2-dichloro-1-methylcyclopropyl)methylsulfanyl]pyridine Chemical compound C=1C=CC=NC=1SCC1(C)CC1(Cl)Cl DTCNNZIBPORQFK-UHFFFAOYSA-N 0.000 description 1
- XLYZVHJRMKEXNY-UHFFFAOYSA-N 2-[(2,2-dichloro-1-methylcyclopropyl)methylsulfonyl]-1-oxidopyridin-1-ium Chemical compound C=1C=CC=[N+]([O-])C=1S(=O)(=O)CC1(C)CC1(Cl)Cl XLYZVHJRMKEXNY-UHFFFAOYSA-N 0.000 description 1
- KFNIYRRSHBNGME-UHFFFAOYSA-N 2-[(2,5-dimethoxyphenyl)methylsulfinyl]-1-oxidopyridin-1-ium Chemical compound COC1=CC=C(OC)C(CS(=O)C=2[N+](=CC=CC=2)[O-])=C1 KFNIYRRSHBNGME-UHFFFAOYSA-N 0.000 description 1
- JEHFGWQCIBRYMA-UHFFFAOYSA-N 2-[(2,6-dichlorophenyl)methylsulfinyl]-1-oxidopyridin-1-ium Chemical compound [O-][N+]1=CC=CC=C1S(=O)CC1=C(Cl)C=CC=C1Cl JEHFGWQCIBRYMA-UHFFFAOYSA-N 0.000 description 1
- USYCJPRHTFHQMJ-UHFFFAOYSA-N 2-[(2-chlorophenyl)methylsulfinyl]pyridine Chemical compound ClC1=C(C=CC=C1)CS(=O)C1=NC=CC=C1 USYCJPRHTFHQMJ-UHFFFAOYSA-N 0.000 description 1
- KUDYTUYGOKELKI-UHFFFAOYSA-N 2-[(2-fluorophenyl)methylsulfinyl]-1-oxidopyridin-1-ium Chemical compound [O-][N+]1=CC=CC=C1S(=O)CC1=CC=CC=C1F KUDYTUYGOKELKI-UHFFFAOYSA-N 0.000 description 1
- VVVHIWKUOXPHOC-UHFFFAOYSA-N 2-[(2-fluorophenyl)methylsulfonyl]-1-oxidopyridin-1-ium Chemical compound [O-][N+]1=CC=CC=C1S(=O)(=O)CC1=CC=CC=C1F VVVHIWKUOXPHOC-UHFFFAOYSA-N 0.000 description 1
- GHUAEOHVHBBXSV-UHFFFAOYSA-N 2-[(2-iodophenyl)methylsulfonyl]-1-oxidopyridin-1-ium Chemical compound [O-][N+]1=CC=CC=C1S(=O)(=O)CC1=CC=CC=C1I GHUAEOHVHBBXSV-UHFFFAOYSA-N 0.000 description 1
- HKMIXSXBUSJGCO-UHFFFAOYSA-N 2-[(2-methoxy-5-methylphenyl)methylsulfonyl]-1-oxidopyridin-1-ium Chemical compound COC1=CC=C(C)C=C1CS(=O)(=O)C1=CC=CC=[N+]1[O-] HKMIXSXBUSJGCO-UHFFFAOYSA-N 0.000 description 1
- QAIOTMSKFQPIOT-UHFFFAOYSA-N 2-[(2-methylnaphthalen-1-yl)methylsulfonyl]-1-oxidopyridin-1-ium Chemical compound CC1=CC=C2C=CC=CC2=C1CS(=O)(=O)C1=CC=CC=[N+]1[O-] QAIOTMSKFQPIOT-UHFFFAOYSA-N 0.000 description 1
- XGLFLMFPBDDIPH-UHFFFAOYSA-N 2-[(2-methylphenyl)methylsulfinyl]pyridine Chemical compound CC1=CC=CC=C1CS(=O)C1=CC=CC=N1 XGLFLMFPBDDIPH-UHFFFAOYSA-N 0.000 description 1
- SAEUPAPRCKADST-UHFFFAOYSA-N 2-[(2-nitrophenyl)methylsulfinyl]-1-oxidopyridin-1-ium Chemical compound [O-][N+](=O)C1=CC=CC=C1CS(=O)C1=CC=CC=[N+]1[O-] SAEUPAPRCKADST-UHFFFAOYSA-N 0.000 description 1
- WPZKLHAUFPIUPN-UHFFFAOYSA-N 2-[(3,4-dichlorophenyl)methylsulfinyl]pyridine Chemical compound C1=C(Cl)C(Cl)=CC=C1CS(=O)C1=CC=CC=N1 WPZKLHAUFPIUPN-UHFFFAOYSA-N 0.000 description 1
- PCUSCGYNVLSRRA-UHFFFAOYSA-N 2-[(3,4-dimethoxyphenyl)methylsulfinyl]-1-oxidopyridin-1-ium Chemical compound C1=C(OC)C(OC)=CC=C1CS(=O)C1=CC=CC=[N+]1[O-] PCUSCGYNVLSRRA-UHFFFAOYSA-N 0.000 description 1
- ZYBOBCNEOFHBOD-UHFFFAOYSA-N 2-[(3,4-dimethoxyphenyl)methylsulfonyl]-1-oxidopyridin-1-ium Chemical compound C1=C(OC)C(OC)=CC=C1CS(=O)(=O)C1=CC=CC=[N+]1[O-] ZYBOBCNEOFHBOD-UHFFFAOYSA-N 0.000 description 1
- JFTICNNRHDKRNO-UHFFFAOYSA-N 2-[(3,4-dimethylphenyl)methylsulfonyl]-1-oxidopyridin-1-ium Chemical compound C1=C(C)C(C)=CC=C1CS(=O)(=O)C1=CC=CC=[N+]1[O-] JFTICNNRHDKRNO-UHFFFAOYSA-N 0.000 description 1
- WRCTXXTYWOQCAV-UHFFFAOYSA-N 2-[(3-bromophenyl)methylsulfonyl]-1-oxidopyridin-1-ium Chemical compound [O-][N+]1=CC=CC=C1S(=O)(=O)CC1=CC=CC(Br)=C1 WRCTXXTYWOQCAV-UHFFFAOYSA-N 0.000 description 1
- AAWFWUAVJXBPHL-UHFFFAOYSA-N 2-[(4-chlorophenyl)methylsulfinyl]-1-oxidopyridin-1-ium Chemical compound [O-][N+]1=CC=CC=C1S(=O)CC1=CC=C(Cl)C=C1 AAWFWUAVJXBPHL-UHFFFAOYSA-N 0.000 description 1
- IGBSOYFNMGVYGL-UHFFFAOYSA-N 2-[(4-chlorophenyl)methylsulfonyl]-1-oxidopyridin-1-ium Chemical compound [O-][N+]1=CC=CC=C1S(=O)(=O)CC1=CC=C(Cl)C=C1 IGBSOYFNMGVYGL-UHFFFAOYSA-N 0.000 description 1
- PYRKKGOKRMZEIT-UHFFFAOYSA-N 2-[6-(2-cyclopropylethoxy)-9-(2-hydroxy-2-methylpropyl)-1h-phenanthro[9,10-d]imidazol-2-yl]-5-fluorobenzene-1,3-dicarbonitrile Chemical compound C1=C2C3=CC(CC(C)(O)C)=CC=C3C=3NC(C=4C(=CC(F)=CC=4C#N)C#N)=NC=3C2=CC=C1OCCC1CC1 PYRKKGOKRMZEIT-UHFFFAOYSA-N 0.000 description 1
- QLEDDIYGHCJEJR-UHFFFAOYSA-N 2-[[2,5-di(propan-2-yl)phenyl]methylsulfonyl]pyridine Chemical compound CC(C)C1=CC=C(C(C)C)C(CS(=O)(=O)C=2N=CC=CC=2)=C1 QLEDDIYGHCJEJR-UHFFFAOYSA-N 0.000 description 1
- ZMESNHCYSFMMPD-UHFFFAOYSA-N 2-benzhydrylsulfinyl-1-oxidopyridin-1-ium Chemical compound [O-][N+]1=CC=CC=C1S(=O)C(C=1C=CC=CC=1)C1=CC=CC=C1 ZMESNHCYSFMMPD-UHFFFAOYSA-N 0.000 description 1
- PSMJATBJEWJPHE-UHFFFAOYSA-N 2-benzylsulfonyl-1-oxidopyridin-1-ium Chemical compound [O-][N+]1=CC=CC=C1S(=O)(=O)CC1=CC=CC=C1 PSMJATBJEWJPHE-UHFFFAOYSA-N 0.000 description 1
- WYSRTEVFLQJJDN-UHFFFAOYSA-N 2-chloro-1-oxidopyridin-1-ium Chemical compound [O-][N+]1=CC=CC=C1Cl WYSRTEVFLQJJDN-UHFFFAOYSA-N 0.000 description 1
- JKCPYFMMHVRDIS-UHFFFAOYSA-N 2-cyclopentylsulfonyl-1-oxidopyridin-1-ium Chemical compound [O-][N+]1=CC=CC=C1S(=O)(=O)C1CCCC1 JKCPYFMMHVRDIS-UHFFFAOYSA-N 0.000 description 1
- VWZODQGCLVRPPR-UHFFFAOYSA-N 2-ethylsulfinyl-1-oxidopyridin-1-ium Chemical compound CCS(=O)C1=CC=CC=[N+]1[O-] VWZODQGCLVRPPR-UHFFFAOYSA-N 0.000 description 1
- ZOIOLSRIKIVXLO-UHFFFAOYSA-N 2-propan-2-ylsulfonylpyridine Chemical compound CC(C)S(=O)(=O)C1=CC=CC=N1 ZOIOLSRIKIVXLO-UHFFFAOYSA-N 0.000 description 1
- RWNISPVLLBWJBU-UHFFFAOYSA-N 2-sulfonyl-1h-pyridine Chemical compound O=S(=O)=C1C=CC=CN1 RWNISPVLLBWJBU-UHFFFAOYSA-N 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- DZWHGWMCGXYGOB-UHFFFAOYSA-N 4-[(1-oxidopyridin-1-ium-2-yl)sulfonylmethyl]benzonitrile Chemical compound [O-][N+]1=CC=CC=C1S(=O)(=O)CC1=CC=C(C#N)C=C1 DZWHGWMCGXYGOB-UHFFFAOYSA-N 0.000 description 1
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 description 1
- BSFODEXXVBBYOC-UHFFFAOYSA-N 8-[4-(dimethylamino)butan-2-ylamino]quinolin-6-ol Chemical compound C1=CN=C2C(NC(CCN(C)C)C)=CC(O)=CC2=C1 BSFODEXXVBBYOC-UHFFFAOYSA-N 0.000 description 1
- 241000209764 Avena fatua Species 0.000 description 1
- 241000217446 Calystegia sepium Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000208296 Datura Species 0.000 description 1
- 241000508725 Elymus repens Species 0.000 description 1
- DNXHEGUUPJUMQT-CBZIJGRNSA-N Estrone Chemical compound OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 DNXHEGUUPJUMQT-CBZIJGRNSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- 241000208204 Linum Species 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 235000010624 Medicago sativa Nutrition 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- 241000208125 Nicotiana Species 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 235000001155 Setaria leucopila Nutrition 0.000 description 1
- 235000010086 Setaria viridis var. viridis Nutrition 0.000 description 1
- 235000000208 Solanum incanum Nutrition 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 229920004890 Triton X-100 Polymers 0.000 description 1
- 239000013504 Triton X-100 Substances 0.000 description 1
- 235000005373 Uvularia sessilifolia Nutrition 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000005108 alkenylthio group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 210000000991 chicken egg Anatomy 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 235000005822 corn Nutrition 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
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 235000021463 dry cake Nutrition 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000009313 farming Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 210000004209 hair Anatomy 0.000 description 1
- 210000002837 heart atrium Anatomy 0.000 description 1
- 238000003973 irrigation Methods 0.000 description 1
- 230000002262 irrigation Effects 0.000 description 1
- 238000002955 isolation Methods 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
- 229910052622 kaolinite Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 235000014571 nuts Nutrition 0.000 description 1
- UYDLBVPAAFVANX-UHFFFAOYSA-N octylphenoxy polyethoxyethanol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(OCCOCCOCCOCCO)C=C1 UYDLBVPAAFVANX-UHFFFAOYSA-N 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- WHMDPDGBKYUEMW-UHFFFAOYSA-N pyridine-2-thiol Chemical compound SC1=CC=CC=N1 WHMDPDGBKYUEMW-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000004550 soluble concentrate Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229940104261 taurate Drugs 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/559,196 US3960542A (en) | 1975-03-17 | 1975-03-17 | Herbicidal 2-sulfinyl and 2-sulfonyl pyridine N-oxide derivatives |
| US05/559,188 US4019893A (en) | 1975-03-17 | 1975-03-17 | Herbicidal method using 2-sulfinyl or 2-sulfonyl pyridine N-oxide derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2609204A1 true DE2609204A1 (de) | 1976-10-07 |
Family
ID=27071993
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762609204 Withdrawn DE2609204A1 (de) | 1975-03-17 | 1976-03-05 | 2-sulfinyl-und 2-sulfonylpyridin- n-oxid-verbindungen |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS51115926A (enExample) |
| AR (1) | AR221680A1 (enExample) |
| CH (2) | CH610722A5 (enExample) |
| CS (1) | CS201538B2 (enExample) |
| DD (2) | DD129731A5 (enExample) |
| DE (1) | DE2609204A1 (enExample) |
| FR (1) | FR2304292A1 (enExample) |
| GB (1) | GB1542881A (enExample) |
| HU (1) | HU178363B (enExample) |
| IT (1) | IT1062195B (enExample) |
| MX (1) | MX3479E (enExample) |
| PL (1) | PL99519B1 (enExample) |
| SU (1) | SU583750A3 (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2716832A1 (de) | 1976-04-16 | 1977-10-27 | Uniroyal Inc | Verfahren zur pflanzenwachstumsregulierung, dafuer geeignete mittel sowie neue pyridin-n-oxide |
| AT389874B (de) * | 1988-04-29 | 1990-02-12 | Agrolinz Agrarchemikalien | Neue pyridyl-thio-ethylazole, verfahren zu deren herstellung und diese enthaltende fungizide mittel |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4503230A (en) * | 1981-08-20 | 1985-03-05 | Uniroyal, Inc. | Alkylation of substituted sulfonylpyridines |
-
1976
- 1976-03-05 DE DE19762609204 patent/DE2609204A1/de not_active Withdrawn
- 1976-03-11 AR AR26252976A patent/AR221680A1/es active
- 1976-03-12 FR FR7607255A patent/FR2304292A1/fr active Granted
- 1976-03-15 JP JP2801876A patent/JPS51115926A/ja active Pending
- 1976-03-15 MX MX7276U patent/MX3479E/es unknown
- 1976-03-16 PL PL18797176A patent/PL99519B1/pl unknown
- 1976-03-16 CS CS169376A patent/CS201538B2/cs unknown
- 1976-03-16 DD DD19775076A patent/DD129731A5/xx unknown
- 1976-03-16 DD DD19187376A patent/DD124876A5/xx unknown
- 1976-03-16 IT IT6762876A patent/IT1062195B/it active
- 1976-03-16 HU HUUI000233 patent/HU178363B/hu unknown
- 1976-03-16 GB GB1047676A patent/GB1542881A/en not_active Expired
- 1976-03-17 CH CH333876A patent/CH610722A5/xx not_active IP Right Cessation
- 1976-08-30 SU SU7602391605A patent/SU583750A3/ru active
-
1979
- 1979-05-09 CH CH435479A patent/CH615667A5/fr not_active IP Right Cessation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2716832A1 (de) | 1976-04-16 | 1977-10-27 | Uniroyal Inc | Verfahren zur pflanzenwachstumsregulierung, dafuer geeignete mittel sowie neue pyridin-n-oxide |
| AT389874B (de) * | 1988-04-29 | 1990-02-12 | Agrolinz Agrarchemikalien | Neue pyridyl-thio-ethylazole, verfahren zu deren herstellung und diese enthaltende fungizide mittel |
Also Published As
| Publication number | Publication date |
|---|---|
| CS201538B2 (en) | 1980-11-28 |
| CH610722A5 (en) | 1979-05-15 |
| SU583750A3 (ru) | 1977-12-05 |
| GB1542881A (en) | 1979-03-28 |
| IT1062195B (it) | 1983-07-28 |
| MX3479E (es) | 1980-12-15 |
| AR221680A1 (es) | 1981-03-13 |
| FR2304292A1 (fr) | 1976-10-15 |
| JPS51115926A (en) | 1976-10-13 |
| CH615667A5 (en) | 1980-02-15 |
| PL99519B1 (pl) | 1978-07-31 |
| FR2304292B1 (enExample) | 1979-01-05 |
| DD129731A5 (de) | 1978-02-08 |
| HU178363B (en) | 1982-04-28 |
| DD124876A5 (enExample) | 1977-03-16 |
| AU1181776A (en) | 1977-09-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8139 | Disposal/non-payment of the annual fee |