CS201538B2 - Herbicide means and method for making the active compon ent ingredient - Google Patents
Herbicide means and method for making the active compon ent ingredient Download PDFInfo
- Publication number
- CS201538B2 CS201538B2 CS169376A CS169376A CS201538B2 CS 201538 B2 CS201538 B2 CS 201538B2 CS 169376 A CS169376 A CS 169376A CS 169376 A CS169376 A CS 169376A CS 201538 B2 CS201538 B2 CS 201538B2
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- Czechoslovakia
- Prior art keywords
- align
- oxide
- pyridine
- phenyl
- compound
- Prior art date
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- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 22
- 238000000034 method Methods 0.000 title claims description 16
- 239000004009 herbicide Substances 0.000 title description 21
- 239000000306 component Substances 0.000 title 1
- 239000004615 ingredient Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 37
- 239000002904 solvent Substances 0.000 claims abstract description 10
- -1 2,2-dichlorocyclopropyl Chemical group 0.000 claims description 53
- 239000000203 mixture Substances 0.000 claims description 30
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 claims description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 25
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 20
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical group OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 19
- 239000011541 reaction mixture Substances 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
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- 238000010992 reflux Methods 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 239000004480 active ingredient Substances 0.000 claims description 7
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
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- XHTYTRJQTACTIW-UHFFFAOYSA-N 2-[1-(4-bromophenyl)ethylsulfonyl]-1-oxidopyridin-1-ium Chemical compound C=1C=CC=[N+]([O-])C=1S(=O)(=O)C(C)C1=CC=C(Br)C=C1 XHTYTRJQTACTIW-UHFFFAOYSA-N 0.000 claims description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
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- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
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- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
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- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
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- NOCHRVHWICTPLG-UHFFFAOYSA-N 1-chloro-4-(1-chloroethyl)benzene Chemical compound CC(Cl)C1=CC=C(Cl)C=C1 NOCHRVHWICTPLG-UHFFFAOYSA-N 0.000 description 1
- RTUCGFDSMXRQAG-UHFFFAOYSA-N 1-oxido-2-[(2,3,6-trichlorophenyl)methylsulfinyl]pyridin-1-ium Chemical compound [O-][N+]1=CC=CC=C1S(=O)CC1=C(Cl)C=CC(Cl)=C1Cl RTUCGFDSMXRQAG-UHFFFAOYSA-N 0.000 description 1
- KWHYQJIWSGCUER-UHFFFAOYSA-N 1-oxido-2-[(2,3,6-trimethylphenyl)methylsulfanyl]pyridin-1-ium Chemical compound CC1=CC=C(C)C(CSC=2[N+](=CC=CC=2)[O-])=C1C KWHYQJIWSGCUER-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- ZPBVKSBGMQFLMA-UHFFFAOYSA-N 2-(1-chloroethyl)-1,4-dimethylbenzene Chemical compound CC(Cl)C1=CC(C)=CC=C1C ZPBVKSBGMQFLMA-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
- APLUORMWZMBYGN-UHFFFAOYSA-N 2-(1-naphthalen-2-ylethylsulfanyl)-1-oxidopyridin-1-ium Chemical compound C=1C=C2C=CC=CC2=CC=1C(C)SC1=CC=CC=[N+]1[O-] APLUORMWZMBYGN-UHFFFAOYSA-N 0.000 description 1
- FTGUKIIWCIPWCR-UHFFFAOYSA-N 2-(2-methylphenyl)-1-oxidopyridin-1-ium Chemical compound CC1=CC=CC=C1C1=CC=CC=[N+]1[O-] FTGUKIIWCIPWCR-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
- 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
- PNNODJXGRKWSGO-UHFFFAOYSA-N 2-[(2,4-dichlorophenyl)methylsulfanyl]-1-oxidopyridin-1-ium Chemical compound [O-][N+]1=CC=CC=C1SCC1=CC=C(Cl)C=C1Cl PNNODJXGRKWSGO-UHFFFAOYSA-N 0.000 description 1
- 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 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
- INXUCTIGSYJUQX-UHFFFAOYSA-N 2-[(2-methylphenyl)methylsulfanyl]-1-oxidopyridin-1-ium Chemical compound CC1=CC=CC=C1CSC1=CC=CC=[N+]1[O-] INXUCTIGSYJUQX-UHFFFAOYSA-N 0.000 description 1
- JQJMMGMAJJESQZ-UHFFFAOYSA-N 2-[(2-methylphenyl)methylsulfonyl]-1-oxidopyridin-1-ium Chemical compound CC1=CC=CC=C1CS(=O)(=O)C1=CC=CC=[N+]1[O-] JQJMMGMAJJESQZ-UHFFFAOYSA-N 0.000 description 1
- NNMVGDTXYHAECL-UHFFFAOYSA-N 2-[1-(2,5-dimethylphenyl)ethylsulfanyl]-1-oxidopyridin-1-ium Chemical compound C=1C(C)=CC=C(C)C=1C(C)SC1=CC=CC=[N+]1[O-] NNMVGDTXYHAECL-UHFFFAOYSA-N 0.000 description 1
- NVVWRNCNFBRMEK-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)ethylsulfanyl]-1-oxidopyridin-1-ium Chemical compound C=1C=C(Cl)C=CC=1C(C)SC1=CC=CC=[N+]1[O-] NVVWRNCNFBRMEK-UHFFFAOYSA-N 0.000 description 1
- CQKFSRKMQSKRRO-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)ethylsulfonyl]-1-oxidopyridin-1-ium Chemical compound C=1C=CC=[N+]([O-])C=1S(=O)(=O)C(C)C1=CC=C(Cl)C=C1 CQKFSRKMQSKRRO-UHFFFAOYSA-N 0.000 description 1
- BJWXXORCMVMTRA-UHFFFAOYSA-N 2-[1-(4-methylphenyl)ethylsulfonyl]-1-oxidopyridin-1-ium Chemical compound C=1C=CC=[N+]([O-])C=1S(=O)(=O)C(C)C1=CC=C(C)C=C1 BJWXXORCMVMTRA-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
- 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
- RYMZHWFUNAGVJD-UHFFFAOYSA-N 2-benzylsulfanyl-1-oxidopyridin-1-ium Chemical compound [O-][N+]1=CC=CC=C1SCC1=CC=CC=C1 RYMZHWFUNAGVJD-UHFFFAOYSA-N 0.000 description 1
- HOFCENCCZVWZEG-UHFFFAOYSA-N 2-benzylsulfinyl-1-oxidopyridin-1-ium Chemical compound [O-][N+]1=CC=CC=C1S(=O)CC1=CC=CC=C1 HOFCENCCZVWZEG-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
- KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 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
- 241001152057 Acalypha virginica Species 0.000 description 1
- 235000006760 Acer pensylvanicum Nutrition 0.000 description 1
- 241000743339 Agrostis Species 0.000 description 1
- 235000007320 Avena fatua Nutrition 0.000 description 1
- 241000209764 Avena fatua Species 0.000 description 1
- 239000005476 Bentazone Substances 0.000 description 1
- 241000219312 Chenopodium Species 0.000 description 1
- 235000009344 Chenopodium album Nutrition 0.000 description 1
- 235000011498 Chenopodium album var missouriense Nutrition 0.000 description 1
- 235000013328 Chenopodium album var. album Nutrition 0.000 description 1
- 235000014052 Chenopodium album var. microphyllum Nutrition 0.000 description 1
- 235000014050 Chenopodium album var. stevensii Nutrition 0.000 description 1
- 235000013012 Chenopodium album var. striatum Nutrition 0.000 description 1
- 244000285774 Cyperus esculentus Species 0.000 description 1
- 235000005853 Cyperus esculentus Nutrition 0.000 description 1
- 244000075634 Cyperus rotundus Species 0.000 description 1
- 240000008853 Datura stramonium Species 0.000 description 1
- 235000013603 Digitaria ischaemum Nutrition 0.000 description 1
- 241000035632 Digitaria ischaemum Species 0.000 description 1
- 241000508725 Elymus repens Species 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 239000005562 Glyphosate Substances 0.000 description 1
- 241001327265 Ischaemum Species 0.000 description 1
- 241000208204 Linum Species 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- 241000120941 Notiosorex crawfordi Species 0.000 description 1
- DSJIAENEZQVBJD-UHFFFAOYSA-N ON(C=CC=C1)C1=S=O Chemical class ON(C=CC=C1)C1=S=O DSJIAENEZQVBJD-UHFFFAOYSA-N 0.000 description 1
- 241000209117 Panicum Species 0.000 description 1
- 235000006443 Panicum miliaceum subsp. miliaceum Nutrition 0.000 description 1
- 235000009037 Panicum miliaceum subsp. ruderale Nutrition 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 235000008515 Setaria glauca Nutrition 0.000 description 1
- 244000010062 Setaria pumila Species 0.000 description 1
- 240000003461 Setaria viridis Species 0.000 description 1
- 235000002248 Setaria viridis 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
- 241001584884 Urochloa texana Species 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
- SNAAJJQQZSMGQD-UHFFFAOYSA-N aluminum magnesium Chemical compound [Mg].[Al] SNAAJJQQZSMGQD-UHFFFAOYSA-N 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
- CNBGNNVCVSKAQZ-UHFFFAOYSA-N benzidamine Natural products C12=CC=CC=C2C(OCCCN(C)C)=NN1CC1=CC=CC=C1 CNBGNNVCVSKAQZ-UHFFFAOYSA-N 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
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 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
- 239000002270 dispersing agent 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
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- 230000005496 eutectics Effects 0.000 description 1
- 229940097068 glyphosate Drugs 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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
- 229920005610 lignin Polymers 0.000 description 1
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-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
- 150000004767 nitrides Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 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
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 230000002786 root growth Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 238000000926 separation method Methods 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
- 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
- 239000004550 soluble concentrate Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- IWOKCMBOJXYDEE-UHFFFAOYSA-N sulfinylmethane Chemical compound C=S=O IWOKCMBOJXYDEE-UHFFFAOYSA-N 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 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
- 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
- 230000000007 visual effect Effects 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 238000005406 washing Methods 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 |
|---|---|
| CS201538B2 true CS201538B2 (en) | 1980-11-28 |
Family
ID=27071993
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS169376A CS201538B2 (en) | 1975-03-17 | 1976-03-16 | Herbicide means and method for making the active compon ent ingredient |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS51115926A (OSRAM) |
| AR (1) | AR221680A1 (OSRAM) |
| CH (2) | CH610722A5 (OSRAM) |
| CS (1) | CS201538B2 (OSRAM) |
| DD (2) | DD129731A5 (OSRAM) |
| DE (1) | DE2609204A1 (OSRAM) |
| FR (1) | FR2304292A1 (OSRAM) |
| GB (1) | GB1542881A (OSRAM) |
| HU (1) | HU178363B (OSRAM) |
| IT (1) | IT1062195B (OSRAM) |
| MX (1) | MX3479E (OSRAM) |
| PL (1) | PL99519B1 (OSRAM) |
| SU (1) | SU583750A3 (OSRAM) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US4503230A (en) * | 1981-08-20 | 1985-03-05 | Uniroyal, Inc. | Alkylation of substituted sulfonylpyridines |
| AT389874B (de) * | 1988-04-29 | 1990-02-12 | Agrolinz Agrarchemikalien | Neue pyridyl-thio-ethylazole, verfahren zu deren herstellung und diese enthaltende fungizide mittel |
-
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
Also Published As
| Publication number | Publication date |
|---|---|
| DE2609204A1 (de) | 1976-10-07 |
| 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 (OSRAM) | 1979-01-05 |
| DD129731A5 (de) | 1978-02-08 |
| HU178363B (en) | 1982-04-28 |
| DD124876A5 (OSRAM) | 1977-03-16 |
| AU1181776A (en) | 1977-09-15 |
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