CA1164867A - Substituted pyridine 1-oxide herbicides - Google Patents
Substituted pyridine 1-oxide herbicidesInfo
- Publication number
- CA1164867A CA1164867A CA000386284A CA386284A CA1164867A CA 1164867 A CA1164867 A CA 1164867A CA 000386284 A CA000386284 A CA 000386284A CA 386284 A CA386284 A CA 386284A CA 1164867 A CA1164867 A CA 1164867A
- Authority
- CA
- Canada
- Prior art keywords
- oxide
- compound
- pyridine
- phenyl
- methyl
- 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.)
- Expired
Links
- 239000004009 herbicide Substances 0.000 title abstract description 16
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical class [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 title description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 35
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 30
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 17
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 16
- 150000002367 halogens Chemical class 0.000 claims abstract description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 14
- 239000001257 hydrogen Substances 0.000 claims abstract description 14
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 10
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 6
- -1 2,5-dimethylphenyl Chemical group 0.000 claims description 34
- 241000196324 Embryophyta Species 0.000 claims description 28
- 239000000460 chlorine Chemical group 0.000 claims description 14
- 230000002363 herbicidal effect Effects 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- LAYCZDKJLFYPNT-UHFFFAOYSA-N 2-[1-(2,5-dimethylphenyl)ethylsulfonyl]-4-methyl-1-oxidopyridin-1-ium Chemical compound C=1C(C)=CC=[N+]([O-])C=1S(=O)(=O)C(C)C1=CC(C)=CC=C1C LAYCZDKJLFYPNT-UHFFFAOYSA-N 0.000 claims description 2
- AKUZLDFQPAHRKH-UHFFFAOYSA-N 2-[1-(2,5-dimethylphenyl)ethylsulfonyl]-5-methyl-1-oxidopyridin-1-ium Chemical compound C=1C=C(C)C=[N+]([O-])C=1S(=O)(=O)C(C)C1=CC(C)=CC=C1C AKUZLDFQPAHRKH-UHFFFAOYSA-N 0.000 claims description 2
- CYAQMXYNPPTVIO-UHFFFAOYSA-N 3-methyl-2-[1-(2-methyl-3-nitrophenyl)ethylsulfonyl]-1-oxidopyridin-1-ium Chemical compound CC=1C=CC=[N+]([O-])C=1S(=O)(=O)C(C)C1=CC=CC([N+]([O-])=O)=C1C CYAQMXYNPPTVIO-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 2
- MNGJENADHMPUKT-UHFFFAOYSA-N 2-[(2,5-dimethylphenyl)methylsulfonyl]-4,5-dimethyl-1-oxidopyridin-1-ium Chemical compound CC1=CC=C(C)C(CS(=O)(=O)C=2[N+](=CC(C)=C(C)C=2)[O-])=C1 MNGJENADHMPUKT-UHFFFAOYSA-N 0.000 claims 1
- JHNURFXKFRMZJF-UHFFFAOYSA-N 2-[(2,5-dimethylphenyl)methylsulfonyl]-4-methyl-1-oxidopyridin-1-ium Chemical compound CC1=CC=C(C)C(CS(=O)(=O)C=2[N+](=CC=C(C)C=2)[O-])=C1 JHNURFXKFRMZJF-UHFFFAOYSA-N 0.000 claims 1
- HVFPEQUCXFQLBO-UHFFFAOYSA-N 2-[1-(2,5-dimethylphenyl)ethylsulfonyl]-3-methyl-1-oxidopyridin-1-ium Chemical compound CC=1C=CC=[N+]([O-])C=1S(=O)(=O)C(C)C1=CC(C)=CC=C1C HVFPEQUCXFQLBO-UHFFFAOYSA-N 0.000 claims 1
- CWZSSSZLIQAZIG-UHFFFAOYSA-N 2-benzylsulfinyl-4-methyl-1-oxidopyridin-1-ium Chemical compound CC1=CC=[N+]([O-])C(S(=O)CC=2C=CC=CC=2)=C1 CWZSSSZLIQAZIG-UHFFFAOYSA-N 0.000 claims 1
- HLVAGRNOKXSWHA-UHFFFAOYSA-N 2-benzylsulfonyl-5-chloro-1-oxidopyridin-1-ium Chemical compound [O-][N+]1=CC(Cl)=CC=C1S(=O)(=O)CC1=CC=CC=C1 HLVAGRNOKXSWHA-UHFFFAOYSA-N 0.000 claims 1
- TZFRXDXILDLCNQ-UHFFFAOYSA-N 3-methyl-2-[(2-methylphenyl)methylsulfonyl]-1-oxidopyridin-1-ium Chemical compound CC1=CC=CC=C1CS(=O)(=O)C1=C(C)C=CC=[N+]1[O-] TZFRXDXILDLCNQ-UHFFFAOYSA-N 0.000 claims 1
- XOWKKULEJAYGEA-UHFFFAOYSA-N 3-methyl-2-[1-(2-methylphenyl)ethylsulfonyl]-1-oxidopyridin-1-ium Chemical compound CC=1C=CC=[N+]([O-])C=1S(=O)(=O)C(C)C1=CC=CC=C1C XOWKKULEJAYGEA-UHFFFAOYSA-N 0.000 claims 1
- YXMNRJNIECKZTH-UHFFFAOYSA-N 5-chloro-2-[(2,5-dimethylphenyl)methylsulfinyl]-1-oxidopyridin-1-ium Chemical compound CC1=CC=C(C)C(CS(=O)C=2[N+](=CC(Cl)=CC=2)[O-])=C1 YXMNRJNIECKZTH-UHFFFAOYSA-N 0.000 claims 1
- DRHKEPFHAHNQEN-UHFFFAOYSA-N 5-chloro-2-[(2,5-dimethylphenyl)methylsulfonyl]pyridine Chemical compound CC1=CC=C(C)C(CS(=O)(=O)C=2N=CC(Cl)=CC=2)=C1 DRHKEPFHAHNQEN-UHFFFAOYSA-N 0.000 claims 1
- QFOZJPFMENGATL-UHFFFAOYSA-N 5-chloro-2-[chloro(phenyl)methyl]sulfonyl-1-oxidopyridin-1-ium Chemical compound [O-][N+]1=CC(Cl)=CC=C1S(=O)(=O)C(Cl)C1=CC=CC=C1 QFOZJPFMENGATL-UHFFFAOYSA-N 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 abstract description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 38
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
- 239000000243 solution Substances 0.000 description 21
- 239000000203 mixture Substances 0.000 description 18
- 239000000126 substance Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000002689 soil Substances 0.000 description 14
- 238000005481 NMR spectroscopy Methods 0.000 description 13
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 13
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 12
- 238000000921 elemental analysis Methods 0.000 description 12
- 239000000047 product Substances 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 239000007787 solid Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 244000105624 Arachis hypogaea Species 0.000 description 6
- 235000010469 Glycine max Nutrition 0.000 description 6
- 244000068988 Glycine max Species 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 239000005457 ice water Substances 0.000 description 6
- 244000237956 Amaranthus retroflexus Species 0.000 description 5
- 229920000742 Cotton Polymers 0.000 description 5
- 241000219146 Gossypium Species 0.000 description 5
- 235000004431 Linum usitatissimum Nutrition 0.000 description 5
- 240000006240 Linum usitatissimum Species 0.000 description 5
- 241001355178 Setaria faberi Species 0.000 description 5
- 235000017016 Setaria faberi Nutrition 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 4
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 4
- 244000061176 Nicotiana tabacum Species 0.000 description 4
- 240000003461 Setaria viridis Species 0.000 description 4
- 235000002248 Setaria viridis Nutrition 0.000 description 4
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 4
- 208000027418 Wounds and injury Diseases 0.000 description 4
- 230000006378 damage Effects 0.000 description 4
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 4
- 208000014674 injury Diseases 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 235000020232 peanut Nutrition 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 235000010777 Arachis hypogaea Nutrition 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
- 244000058871 Echinochloa crus-galli Species 0.000 description 3
- 244000025670 Eleusine indica Species 0.000 description 3
- 235000014716 Eleusine indica Nutrition 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- 240000004658 Medicago sativa Species 0.000 description 3
- 241001520808 Panicum virgatum Species 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 235000010086 Setaria viridis var. viridis Nutrition 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 239000004495 emulsifiable concentrate Substances 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- 229940083608 sodium hydroxide Drugs 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 239000004563 wettable powder Substances 0.000 description 3
- VGARSXYWKORGCJ-UHFFFAOYSA-N (2,5-dimethylphenyl)methanethiol Chemical compound CC1=CC=C(C)C(CS)=C1 VGARSXYWKORGCJ-UHFFFAOYSA-N 0.000 description 2
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 2
- 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 2
- XUUPWPRPQMGAFE-UHFFFAOYSA-N 2-bromo-4-methyl-1-oxidopyridin-1-ium;hydrochloride Chemical compound Cl.CC1=CC=[N+]([O-])C(Br)=C1 XUUPWPRPQMGAFE-UHFFFAOYSA-N 0.000 description 2
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
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- 235000007320 Avena fatua Nutrition 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 235000009344 Chenopodium album Nutrition 0.000 description 2
- 235000005484 Chenopodium berlandieri Nutrition 0.000 description 2
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- 241000508725 Elymus repens Species 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 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
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
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- 240000003768 Solanum lycopersicum Species 0.000 description 2
- 241001584884 Urochloa texana Species 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
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- 239000011737 fluorine Substances 0.000 description 2
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- 239000008187 granular material Substances 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 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
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- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
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- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 2
- 150000003871 sulfonates Chemical class 0.000 description 2
- 150000003457 sulfones Chemical class 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- PTDVPWWJRCOIIO-UHFFFAOYSA-N (4-methoxyphenyl)methanethiol Chemical compound COC1=CC=C(CS)C=C1 PTDVPWWJRCOIIO-UHFFFAOYSA-N 0.000 description 1
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- WSYIZLFZUDANGU-UHFFFAOYSA-N 2-[(2,5-dimethylphenyl)methylsulfonyl]-3-methyl-1-oxidopyridin-1-ium Chemical compound CC1=CC=C(C)C(CS(=O)(=O)C=2[N+](=CC=CC=2C)[O-])=C1 WSYIZLFZUDANGU-UHFFFAOYSA-N 0.000 description 1
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- AGYKUIGAUZEWSU-UHFFFAOYSA-N 2-bromo-1-oxido-4-phenylpyridin-1-ium;hydrochloride Chemical compound Cl.C1=C(Br)[N+]([O-])=CC=C1C1=CC=CC=C1 AGYKUIGAUZEWSU-UHFFFAOYSA-N 0.000 description 1
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- PGIZFEZRSHXAFF-UHFFFAOYSA-N 2-bromo-5-methyl-1-oxidopyridin-1-ium;hydrochloride Chemical compound Cl.CC1=CC=C(Br)[N+]([O-])=C1 PGIZFEZRSHXAFF-UHFFFAOYSA-N 0.000 description 1
- ZGHMADNNOPPAJO-UHFFFAOYSA-N 2-chloro-3-methyl-1-oxidopyridin-1-ium Chemical compound CC1=CC=C[N+]([O-])=C1Cl ZGHMADNNOPPAJO-UHFFFAOYSA-N 0.000 description 1
- FYKQMHHUPQCHNO-UHFFFAOYSA-N 2-chloro-3-methyl-1-oxidopyridin-1-ium;hydrochloride Chemical compound Cl.CC1=CC=C[N+]([O-])=C1Cl FYKQMHHUPQCHNO-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- NEXUNCTUUDERGR-UHFFFAOYSA-N 3-chloro-1-oxidopyridin-1-ium Chemical compound [O-][N+]1=CC=CC(Cl)=C1 NEXUNCTUUDERGR-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 1
- 240000001592 Amaranthus caudatus Species 0.000 description 1
- 241000272814 Anser sp. Species 0.000 description 1
- 241000209764 Avena fatua Species 0.000 description 1
- 244000075850 Avena orientalis Species 0.000 description 1
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 240000008067 Cucumis sativus Species 0.000 description 1
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 1
- 235000013603 Digitaria ischaemum Nutrition 0.000 description 1
- 241000035632 Digitaria ischaemum Species 0.000 description 1
- 101000864663 Drosophila melanogaster ATP-dependent RNA helicase DHX8 Proteins 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- 241000207890 Ipomoea purpurea Species 0.000 description 1
- 241001508691 Martes zibellina Species 0.000 description 1
- 235000017587 Medicago sativa ssp. sativa Nutrition 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 241000209504 Poaceae Species 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
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 235000021536 Sugar beet Nutrition 0.000 description 1
- 229920004890 Triton X-100 Polymers 0.000 description 1
- 235000005373 Uvularia sessilifolia Nutrition 0.000 description 1
- 101100184148 Xenopus laevis mix-a gene Proteins 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
- 229960000583 acetic acid Drugs 0.000 description 1
- 230000009418 agronomic effect Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- SNAAJJQQZSMGQD-UHFFFAOYSA-N aluminum magnesium Chemical compound [Mg].[Al] SNAAJJQQZSMGQD-UHFFFAOYSA-N 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 239000006227 byproduct Substances 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
- 238000001816 cooling Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 244000038559 crop plants Species 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- LRCFXGAMWKDGLA-UHFFFAOYSA-N dioxosilane;hydrate Chemical compound O.O=[Si]=O LRCFXGAMWKDGLA-UHFFFAOYSA-N 0.000 description 1
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052622 kaolinite Inorganic materials 0.000 description 1
- CYPPCCJJKNISFK-UHFFFAOYSA-J kaolinite Chemical compound [OH-].[OH-].[OH-].[OH-].[Al+3].[Al+3].[O-][Si](=O)O[Si]([O-])=O CYPPCCJJKNISFK-UHFFFAOYSA-J 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- QEIOAAJCOKZGDV-UHFFFAOYSA-N methylsulfonylformonitrile Chemical compound CS(=O)(=O)C#N QEIOAAJCOKZGDV-UHFFFAOYSA-N 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 239000003960 organic solvent Substances 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
- 231100000208 phytotoxic Toxicity 0.000 description 1
- 230000000885 phytotoxic effect 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
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229940093956 potassium carbonate Drugs 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229940001593 sodium carbonate Drugs 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- XMVONEAAOPAGAO-UHFFFAOYSA-N sodium tungstate Chemical compound [Na+].[Na+].[O-][W]([O-])(=O)=O XMVONEAAOPAGAO-UHFFFAOYSA-N 0.000 description 1
- PWWJJDVDTKXWOF-UHFFFAOYSA-M sodium;2-[hexadecanoyl(methyl)amino]ethanesulfonate Chemical compound [Na+].CCCCCCCCCCCCCCCC(=O)N(C)CCS([O-])(=O)=O PWWJJDVDTKXWOF-UHFFFAOYSA-M 0.000 description 1
- 239000004016 soil organic matter Substances 0.000 description 1
- 239000012265 solid product Substances 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
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- PFXVKGGZWQQTSE-UHFFFAOYSA-N sulfuryl dicyanide Chemical compound N#CS(=O)(=O)C#N PFXVKGGZWQQTSE-UHFFFAOYSA-N 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 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
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
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/231,813 US4394155A (en) | 1981-02-05 | 1981-02-05 | Substituted pyridine 1-oxide herbicides |
| US231,813 | 1981-02-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1164867A true CA1164867A (en) | 1984-04-03 |
Family
ID=22870730
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000386284A Expired CA1164867A (en) | 1981-02-05 | 1981-09-21 | Substituted pyridine 1-oxide herbicides |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4394155A (Direct) |
| JP (1) | JPS57181059A (Direct) |
| KR (1) | KR830008493A (Direct) |
| AU (1) | AU8018182A (Direct) |
| BR (1) | BR8200603A (Direct) |
| CA (1) | CA1164867A (Direct) |
| GR (1) | GR76053B (Direct) |
| IE (1) | IE820256L (Direct) |
| IL (1) | IL64921A0 (Direct) |
| RO (1) | RO84458B (Direct) |
| ZA (1) | ZA82642B (Direct) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19500758A1 (de) * | 1995-01-13 | 1996-07-18 | Basf Ag | Substituierte 2-Phenylpyridine |
| KR101278609B1 (ko) * | 2004-09-03 | 2013-06-25 | 신젠타 리미티드 | 이속사졸린 유도체 및 제초제로서의 그들의 용도 |
| CL2008000376A1 (es) * | 2007-02-09 | 2008-08-18 | Du Pont | Compuestos derivados de n-oxidos de piridina; composicion herbicida; y metodo para controlar el crecimiento de vegetacion indeseada. |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3107994A (en) * | 1959-05-01 | 1963-10-22 | Monsanto Chemicals | Controlling vegetation with alkenyl thiopyridine oxides |
| US3155671A (en) * | 1962-03-19 | 1964-11-03 | Monsanto Co | Benzyl thiopyridine oxides |
| US4026937A (en) * | 1974-01-22 | 1977-05-31 | The Dow Chemical Company | Substituted pyridinylalkoxy-, pyridinylalkylsulfonyl- and pyridinylalkylthio-phenylureas |
| US4019893A (en) * | 1975-03-17 | 1977-04-26 | Uniroyal Inc. | Herbicidal method using 2-sulfinyl or 2-sulfonyl pyridine N-oxide derivatives |
| US3960542A (en) * | 1975-03-17 | 1976-06-01 | Uniroyal Inc. | Herbicidal 2-sulfinyl and 2-sulfonyl pyridine N-oxide derivatives |
| US4050921A (en) * | 1976-04-16 | 1977-09-27 | Uniroyal Inc. | Regulation of the natural growth or development of plants with 2-sulfinyl or 2-sulfonyl pyridine N-oxide compounds |
| US4201567A (en) * | 1979-01-19 | 1980-05-06 | E. I. Du Pont De Nemours And Company | Herbicidal pyridine, 1-oxides |
| US4360677A (en) * | 1979-09-20 | 1982-11-23 | Uniroyal, Inc. | Herbicidal 2-(alpha-chloromethylsulfonyl) pyridine-1-oxides |
-
1981
- 1981-02-05 US US06/231,813 patent/US4394155A/en not_active Expired - Fee Related
- 1981-09-21 CA CA000386284A patent/CA1164867A/en not_active Expired
-
1982
- 1982-02-01 ZA ZA82642A patent/ZA82642B/xx unknown
- 1982-02-03 GR GR67196A patent/GR76053B/el unknown
- 1982-02-03 IL IL64921A patent/IL64921A0/xx unknown
- 1982-02-04 KR KR1019820000456A patent/KR830008493A/ko active Pending
- 1982-02-04 JP JP57016955A patent/JPS57181059A/ja active Pending
- 1982-02-04 AU AU80181/82A patent/AU8018182A/en not_active Abandoned
- 1982-02-04 RO RO106528A patent/RO84458B/ro unknown
- 1982-02-04 BR BR8200603A patent/BR8200603A/pt unknown
- 1982-02-05 IE IE820256A patent/IE820256L/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| RO84458B (ro) | 1984-08-30 |
| JPS57181059A (en) | 1982-11-08 |
| RO84458A (ro) | 1984-06-21 |
| IL64921A0 (en) | 1982-04-30 |
| GR76053B (Direct) | 1984-08-03 |
| KR830008493A (ko) | 1983-12-10 |
| US4394155A (en) | 1983-07-19 |
| BR8200603A (pt) | 1982-12-14 |
| AU8018182A (en) | 1982-08-12 |
| IE820256L (en) | 1982-08-05 |
| ZA82642B (en) | 1982-12-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |