CA2876192C - Production of n-substituted sulfoximine pyridine n-oxides - Google Patents
Production of n-substituted sulfoximine pyridine n-oxides Download PDFInfo
- Publication number
- CA2876192C CA2876192C CA2876192A CA2876192A CA2876192C CA 2876192 C CA2876192 C CA 2876192C CA 2876192 A CA2876192 A CA 2876192A CA 2876192 A CA2876192 A CA 2876192A CA 2876192 C CA2876192 C CA 2876192C
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- Prior art keywords
- compound
- formula
- oxidation
- ethyl
- compounds
- Prior art date
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- 238000004519 manufacturing process Methods 0.000 title claims abstract description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title claims description 13
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 title claims description 6
- 125000005555 sulfoximide group Chemical class 0.000 title description 6
- 238000000034 method Methods 0.000 claims abstract description 22
- -1 N-substituted sulfoximine N-oxides Chemical class 0.000 claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims description 57
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 51
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 38
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 27
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 claims description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
- 230000003647 oxidation Effects 0.000 claims description 12
- 238000007254 oxidation reaction Methods 0.000 claims description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- AQLJVWUFPCUVLO-UHFFFAOYSA-N urea hydrogen peroxide Chemical compound OO.NC(N)=O AQLJVWUFPCUVLO-UHFFFAOYSA-N 0.000 claims description 7
- 239000002798 polar solvent Substances 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 125000001246 bromo group Chemical group Br* 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 18
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
- 239000000203 mixture Substances 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 13
- 238000004809 thin layer chromatography Methods 0.000 description 11
- 239000002904 solvent Substances 0.000 description 10
- 238000003756 stirring Methods 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- 241000607479 Yersinia pestis Species 0.000 description 6
- 238000005903 acid hydrolysis reaction Methods 0.000 description 6
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 6
- 238000003818 flash chromatography Methods 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 4
- 239000000575 pesticide Substances 0.000 description 4
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 239000007832 Na2SO4 Substances 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000013058 crude material Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000000369 oxido group Chemical group [*]=O 0.000 description 2
- 230000000361 pesticidal effect Effects 0.000 description 2
- 239000011369 resultant mixture Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical class [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- ABEXEQSGABRUHS-UHFFFAOYSA-N 16-methylheptadecyl 16-methylheptadecanoate Chemical compound CC(C)CCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCC(C)C ABEXEQSGABRUHS-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241000764238 Isis Species 0.000 description 1
- 241000256602 Isoptera Species 0.000 description 1
- 239000005934 Sulfoxaflor Substances 0.000 description 1
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000005417 image-selected in vivo spectroscopy Methods 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 238000012739 integrated shape imaging system Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical class [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
-
- 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
- A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Pest Control & Pesticides (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261666808P | 2012-06-30 | 2012-06-30 | |
| US201261666807P | 2012-06-30 | 2012-06-30 | |
| US61/666,808 | 2012-06-30 | ||
| US61/666,807 | 2012-06-30 | ||
| PCT/US2013/045556 WO2014004094A1 (en) | 2012-06-30 | 2013-06-13 | Production of n-substituted sulfoximine pyridine n-oxides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2876192A1 CA2876192A1 (en) | 2014-01-03 |
| CA2876192C true CA2876192C (en) | 2021-01-05 |
Family
ID=49778790
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2876192A Active CA2876192C (en) | 2012-06-30 | 2013-06-13 | Production of n-substituted sulfoximine pyridine n-oxides |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US9000180B2 (enEXAMPLES) |
| EP (1) | EP2866564B1 (enEXAMPLES) |
| JP (1) | JP6387000B2 (enEXAMPLES) |
| KR (1) | KR102089479B1 (enEXAMPLES) |
| CN (1) | CN104582488A (enEXAMPLES) |
| AR (1) | AR092849A1 (enEXAMPLES) |
| AU (1) | AU2013280925B2 (enEXAMPLES) |
| BR (1) | BR112014033006B8 (enEXAMPLES) |
| CA (1) | CA2876192C (enEXAMPLES) |
| CO (1) | CO7160112A2 (enEXAMPLES) |
| HK (1) | HK1209278A1 (enEXAMPLES) |
| IL (1) | IL236478A0 (enEXAMPLES) |
| IN (1) | IN2014DN11218A (enEXAMPLES) |
| MX (1) | MX352996B (enEXAMPLES) |
| NZ (1) | NZ702523A (enEXAMPLES) |
| RU (1) | RU2628287C2 (enEXAMPLES) |
| WO (1) | WO2014004094A1 (enEXAMPLES) |
| ZA (1) | ZA201408994B (enEXAMPLES) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX358553B (es) * | 2012-06-30 | 2018-08-24 | Dow Agrosciences Llc | N-óxidos de piridina y procesos para su preparación. |
| CN105503672A (zh) * | 2015-12-06 | 2016-04-20 | 杨秀娟 | 一种药物中间体芳基砜类化合物的合成方法 |
Family Cites Families (30)
| 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 |
| US4212870A (en) | 1979-06-18 | 1980-07-15 | Gulf Oil Corporation | 1-(2,6-Dichlorobenzoyl)-3-(5-chloro-2-pyridinyl-N-oxide)urea and use as insecticide |
| EP0350237A3 (en) * | 1988-07-08 | 1990-08-29 | Schering Agrochemicals Limited | Triazole insecticides |
| IL99445A (en) * | 1990-09-18 | 1996-06-18 | Ciba Geigy Ag | Picoline oxides process for their preparation and insecticidal and acaricidal compositions containing them |
| JP2994182B2 (ja) * | 1992-07-23 | 1999-12-27 | 石原産業株式会社 | アミド系化合物又はその塩、それらの製造方法及びそれらを含有する有害動物防除剤 |
| JP2001515888A (ja) * | 1997-09-08 | 2001-09-25 | ノバルティス アクチエンゲゼルシャフト | 農薬としてのヘテロ環式化合物 |
| JP2002511461A (ja) * | 1998-04-08 | 2002-04-16 | ノバルティス アクチエンゲゼルシャフト | Ｎ−ピリドニル除草剤 |
| DE10130397A1 (de) * | 2001-06-23 | 2003-01-09 | Bayer Cropscience Gmbh | Herbizide substituierte Pyridine, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbzide und Pflanzenwachstumsregulatoren |
| WO2003027099A1 (en) * | 2001-09-21 | 2003-04-03 | E. I. Du Pont De Nemours And Company | Arthropodicidal anthranilamides |
| JP4453320B2 (ja) * | 2002-09-30 | 2010-04-21 | 萬有製薬株式会社 | Ｎ−置換−２−オキソジヒドロピリジン誘導体 |
| JP2004238307A (ja) * | 2003-02-04 | 2004-08-26 | Ishihara Sangyo Kaisha Ltd | アミド系化合物又はその塩、それらの製造方法及びそれらを含有する有害動物防除剤 |
| JP2005162732A (ja) * | 2003-11-13 | 2005-06-23 | Bayer Cropscience Ag | 殺虫性ニコチノイルカーバメート類 |
| JP4875608B2 (ja) * | 2004-04-08 | 2012-02-15 | ダウ アグロサイエンシィズ エルエルシー | 殺虫性ｎ−置換スルホキシイミン類 |
| PL1907382T3 (pl) * | 2005-07-26 | 2016-01-29 | Bial Portela & Ca Sa | Pochodne nitrokatecholowe jako inhibitory COMT |
| TWI398433B (zh) * | 2006-02-10 | 2013-06-11 | Dow Agrosciences Llc | 殺蟲性之ｎ-取代（６-鹵烷基吡啶-３-基）烷基磺醯亞胺 |
| TWI383973B (zh) | 2006-08-07 | 2013-02-01 | Dow Agrosciences Llc | 用於製備２-取代-５-（１-烷硫基）烷基吡啶之方法 |
| EP2057150A1 (en) * | 2006-08-22 | 2009-05-13 | Basf Se | Thiophene-sulfonic acid picolyl amides |
| TWI387585B (zh) | 2006-09-01 | 2013-03-01 | Dow Agrosciences Llc | 殺蟲性之ｎ-取代（雜芳基）烷基烴基硫亞胺 |
| US7511149B2 (en) | 2007-02-09 | 2009-03-31 | Dow Agrosciences Llc | Process for the oxidation of certain substituted sulfilimines to insecticidal sulfoximines |
| CA2678028C (en) | 2007-02-26 | 2015-02-03 | Dow Agrosciences Llc | Process for the preparation of certain substituted sulfilimines |
| US8193222B1 (en) | 2007-02-26 | 2012-06-05 | Dow AgroSciences, L.L.C. | Process for the preparation of certain substituted sulfilimines |
| JP2009029787A (ja) * | 2007-06-22 | 2009-02-12 | Ishihara Sangyo Kaisha Ltd | Ｎ−フェニル−メタナミン誘導体及びこれを含有する有害生物防除剤 |
| EP2170066B1 (en) * | 2007-07-27 | 2012-02-29 | Dow AgroSciences LLC | Pesticides and uses thereof |
| WO2009111309A1 (en) | 2008-03-03 | 2009-09-11 | Dow Agrosciences Llc | Pesticides |
| DK2315750T3 (da) | 2008-07-01 | 2013-02-18 | Dow Agrosciences Llc | Forbedret fremgangsmåde til fremstilling af 2-trifluormethyl-5-(1-substituerede) alkylpyridiner |
| KR101736078B1 (ko) * | 2008-12-26 | 2017-05-16 | 다우 아그로사이언시즈 엘엘씨 | 안정한 살충제 조성물 및 이의 제조방법 |
| WO2011009804A2 (en) * | 2009-07-24 | 2011-01-27 | Basf Se | Pyridine derivatives compounds for controlling invertebrate pests |
| EP2468097A1 (en) * | 2010-12-21 | 2012-06-27 | Bayer CropScience AG | Use of Isothiazolecarboxamides to create latent host defenses in a plant |
| CN104582484A (zh) * | 2012-06-30 | 2015-04-29 | 美国陶氏益农公司 | 杀虫性的n-取代的硫亚胺和磺基肟吡啶n-氧化物 |
| MX358553B (es) * | 2012-06-30 | 2018-08-24 | Dow Agrosciences Llc | N-óxidos de piridina y procesos para su preparación. |
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- 2013-06-13 MX MX2014015696A patent/MX352996B/es active IP Right Grant
- 2013-06-13 KR KR1020147036274A patent/KR102089479B1/ko active Active
- 2013-06-13 NZ NZ702523A patent/NZ702523A/en unknown
- 2013-06-13 JP JP2015520251A patent/JP6387000B2/ja not_active Expired - Fee Related
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- 2013-06-13 CA CA2876192A patent/CA2876192C/en active Active
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- 2013-06-13 BR BR112014033006A patent/BR112014033006B8/pt not_active IP Right Cessation
- 2013-06-13 CN CN201380044662.2A patent/CN104582488A/zh active Pending
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Also Published As
| Publication number | Publication date |
|---|---|
| JP2015522588A (ja) | 2015-08-06 |
| RU2015102949A (ru) | 2016-08-20 |
| JP6387000B2 (ja) | 2018-09-05 |
| EP2866564A1 (en) | 2015-05-06 |
| KR20150032539A (ko) | 2015-03-26 |
| US9000180B2 (en) | 2015-04-07 |
| EP2866564B1 (en) | 2020-02-12 |
| RU2628287C2 (ru) | 2017-08-15 |
| WO2014004094A1 (en) | 2014-01-03 |
| IN2014DN11218A (enEXAMPLES) | 2015-10-02 |
| AR092849A1 (es) | 2015-05-06 |
| MX2014015696A (es) | 2015-08-06 |
| ZA201408994B (en) | 2016-08-31 |
| CN104582488A (zh) | 2015-04-29 |
| BR112014033006B8 (pt) | 2022-10-11 |
| US20140005406A1 (en) | 2014-01-02 |
| MX352996B (es) | 2017-12-15 |
| IL236478A0 (en) | 2015-02-26 |
| AU2013280925A1 (en) | 2014-12-18 |
| NZ702523A (en) | 2016-07-29 |
| AU2013280925B2 (en) | 2016-09-29 |
| HK1209278A1 (en) | 2016-04-01 |
| CA2876192A1 (en) | 2014-01-03 |
| CO7160112A2 (es) | 2015-01-15 |
| BR112014033006A2 (pt) | 2017-06-27 |
| BR112014033006B1 (pt) | 2020-03-03 |
| EP2866564A4 (en) | 2016-02-24 |
| KR102089479B1 (ko) | 2020-03-17 |
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