CA1068709A - Pyridine-n-oxide compounds - Google Patents
Pyridine-n-oxide compoundsInfo
- Publication number
- CA1068709A CA1068709A CA230,796A CA230796A CA1068709A CA 1068709 A CA1068709 A CA 1068709A CA 230796 A CA230796 A CA 230796A CA 1068709 A CA1068709 A CA 1068709A
- Authority
- CA
- Canada
- Prior art keywords
- compound
- formula
- acid
- hydrogen
- compounds
- 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
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical class [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
- 239000001257 hydrogen Substances 0.000 claims abstract description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- 241001124076 Aphididae Species 0.000 claims description 7
- 150000003254 radicals Chemical class 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 230000001590 oxidative effect Effects 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- 230000001473 noxious effect Effects 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 10
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 241000196324 Embryophyta Species 0.000 description 5
- 150000001204 N-oxides Chemical class 0.000 description 5
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 241001425390 Aphis fabae Species 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 240000006677 Vicia faba Species 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- -1 dimethylamino-carbonyl Chemical group 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 150000004965 peroxy acids Chemical class 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-N sodium;hydron;carbonate Chemical compound [Na+].OC(O)=O UIIMBOGNXHQVGW-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- DYTQHZPRTLVBHP-UHFFFAOYSA-N (2-methyl-1-oxidoquinolin-1-ium-4-yl) n,n-dimethylcarbamate Chemical compound C1=CC=C2C(OC(=O)N(C)C)=CC(C)=[N+]([O-])C2=C1 DYTQHZPRTLVBHP-UHFFFAOYSA-N 0.000 description 2
- GLVYLTSKTCWWJR-UHFFFAOYSA-N 2-carbonoperoxoylbenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1C(O)=O GLVYLTSKTCWWJR-UHFFFAOYSA-N 0.000 description 2
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 2
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000004606 Fillers/Extenders Substances 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 241000721621 Myzus persicae Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 235000002096 Vicia faba var. equina Nutrition 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000012876 carrier material Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 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 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- ZOOQYWPHPHVLRU-UHFFFAOYSA-N (2,6-dimethyl-1-oxidopyridin-1-ium-4-yl) N,N-dimethylcarbamate Chemical compound CN(C)C(=O)OC1=CC(C)=[N+]([O-])C(C)=C1 ZOOQYWPHPHVLRU-UHFFFAOYSA-N 0.000 description 1
- ZRGHQYBDXCTONF-UHFFFAOYSA-N (2,6-dimethylpyridin-4-yl) n,n-dimethylcarbamate Chemical compound CN(C)C(=O)OC1=CC(C)=NC(C)=C1 ZRGHQYBDXCTONF-UHFFFAOYSA-N 0.000 description 1
- AHCWOIYNWFUSQR-UHFFFAOYSA-N (2-methylquinolin-4-yl) n,n-dimethylcarbamate Chemical compound C1=CC=C2C(OC(=O)N(C)C)=CC(C)=NC2=C1 AHCWOIYNWFUSQR-UHFFFAOYSA-N 0.000 description 1
- AYKIXQCTKTVYMT-UHFFFAOYSA-N (6-methoxy-2-methyl-5,6,7,8-tetrahydroquinolin-4-yl) n,n-dimethylcarbamate Chemical compound CC1=CC(OC(=O)N(C)C)=C2CC(OC)CCC2=N1 AYKIXQCTKTVYMT-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- XYPISWUKQGWYGX-UHFFFAOYSA-N 2,2,2-trifluoroethaneperoxoic acid Chemical compound OOC(=O)C(F)(F)F XYPISWUKQGWYGX-UHFFFAOYSA-N 0.000 description 1
- GCNTZFIIOFTKIY-UHFFFAOYSA-N 4-hydroxypyridine Chemical class OC1=CC=NC=C1 GCNTZFIIOFTKIY-UHFFFAOYSA-N 0.000 description 1
- 241000238876 Acari Species 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000726735 Aphis schneideri Species 0.000 description 1
- 241000208293 Capsicum Species 0.000 description 1
- 235000002566 Capsicum Nutrition 0.000 description 1
- 240000004160 Capsicum annuum Species 0.000 description 1
- 241000255749 Coccinellidae Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241000917107 Eriosoma lanigerum Species 0.000 description 1
- 241000917171 Eriosomatinae Species 0.000 description 1
- 102100030500 Heparin cofactor 2 Human genes 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 101001082432 Homo sapiens Heparin cofactor 2 Proteins 0.000 description 1
- 241001371826 Ichneumon suspiciosus Species 0.000 description 1
- 241001094479 Myzaphis Species 0.000 description 1
- 241000587784 Pemphis Species 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 241000916759 Tamalia coweni Species 0.000 description 1
- 235000010749 Vicia faba Nutrition 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- SPXSEZMVRJLHQG-XMMPIXPASA-N [(2R)-1-[[4-[(3-phenylmethoxyphenoxy)methyl]phenyl]methyl]pyrrolidin-2-yl]methanol Chemical compound C(C1=CC=CC=C1)OC=1C=C(OCC2=CC=C(CN3[C@H](CCC3)CO)C=C2)C=CC=1 SPXSEZMVRJLHQG-XMMPIXPASA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000001390 capsicum minimum Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
- 229940127271 compound 49 Drugs 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
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000010459 dolomite Substances 0.000 description 1
- 229910000514 dolomite Inorganic materials 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000002316 fumigant Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052622 kaolinite Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229920000847 nonoxynol Polymers 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- XCRBXWCUXJNEFX-UHFFFAOYSA-N peroxybenzoic acid Chemical class OOC(=O)C1=CC=CC=C1 XCRBXWCUXJNEFX-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 239000011505 plaster Substances 0.000 description 1
- 229920001451 polypropylene glycol 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
- 244000062645 predators Species 0.000 description 1
- CZPZWMPYEINMCF-UHFFFAOYSA-N propaneperoxoic acid Chemical compound CCC(=O)OO CZPZWMPYEINMCF-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- UCNVFYAIKDJUDC-UHFFFAOYSA-N quinolin-1-ium;carbamate Chemical class NC(O)=O.N1=CC=CC2=CC=CC=C21 UCNVFYAIKDJUDC-UHFFFAOYSA-N 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- IZWPGJFSBABFGL-GMFCBQQYSA-M sodium;2-[methyl-[(z)-octadec-9-enoyl]amino]ethanesulfonate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCC(=O)N(C)CCS([O-])(=O)=O IZWPGJFSBABFGL-GMFCBQQYSA-M 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000004809 thin layer chromatography 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/58—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems with hetero atoms directly attached to the ring nitrogen atom
- C07D215/60—N-oxides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2432635A DE2432635A1 (de) | 1974-07-06 | 1974-07-06 | Insektizide mittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1068709A true CA1068709A (en) | 1979-12-25 |
Family
ID=5919943
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA230,796A Expired CA1068709A (en) | 1974-07-06 | 1975-07-04 | Pyridine-n-oxide compounds |
Country Status (31)
| Country | Link |
|---|---|
| JP (1) | JPS5132736A (id) |
| AT (1) | AT347742B (id) |
| BE (1) | BE831085A (id) |
| BG (1) | BG25194A3 (id) |
| CA (1) | CA1068709A (id) |
| CH (1) | CH609684A5 (id) |
| CS (1) | CS188229B2 (id) |
| DD (1) | DD122774A5 (id) |
| DE (1) | DE2432635A1 (id) |
| DK (1) | DK142198C (id) |
| EG (1) | EG11799A (id) |
| ES (1) | ES439008A1 (id) |
| FI (1) | FI58773C (id) |
| FR (1) | FR2277085A1 (id) |
| GB (1) | GB1454743A (id) |
| HK (1) | HK73878A (id) |
| HU (1) | HU171770B (id) |
| IE (1) | IE41486B1 (id) |
| IN (1) | IN139584B (id) |
| IT (1) | IT1039715B (id) |
| KE (1) | KE2902A (id) |
| LU (1) | LU72905A1 (id) |
| MY (1) | MY7800483A (id) |
| NL (1) | NL7507813A (id) |
| OA (1) | OA05046A (id) |
| RO (1) | RO72908A (id) |
| SE (1) | SE7507707L (id) |
| SU (1) | SU607528A3 (id) |
| TR (1) | TR18212A (id) |
| ZA (1) | ZA754052B (id) |
| ZM (1) | ZM8675A1 (id) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2570343B2 (ja) * | 1987-12-08 | 1997-01-08 | 東ソー株式会社 | カーバメイト誘導体 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH486841A (de) * | 1965-05-17 | 1970-03-15 | Ciba Geigy | Schädlingsbekämpfungsmittel bzw. ein vor dem Befall durch Schädlinge geschütztes nichttextiles Erzeugnis |
-
1974
- 1974-07-06 DE DE2432635A patent/DE2432635A1/de not_active Withdrawn
-
1975
- 1975-06-25 IN IN1249/CAL/75A patent/IN139584B/en unknown
- 1975-06-25 ZA ZA00754052A patent/ZA754052B/xx unknown
- 1975-06-30 ES ES439008A patent/ES439008A1/es not_active Expired
- 1975-07-01 NL NL7507813A patent/NL7507813A/xx not_active Application Discontinuation
- 1975-07-01 BG BG030434A patent/BG25194A3/xx unknown
- 1975-07-01 SU SU752150554A patent/SU607528A3/ru active
- 1975-07-02 EG EG381/75A patent/EG11799A/xx active
- 1975-07-03 FI FI751941A patent/FI58773C/fi not_active IP Right Cessation
- 1975-07-03 OA OA55546A patent/OA05046A/xx unknown
- 1975-07-03 CH CH870875A patent/CH609684A5/xx not_active IP Right Cessation
- 1975-07-04 LU LU72905A patent/LU72905A1/xx unknown
- 1975-07-04 HU HU75HO00001816A patent/HU171770B/hu unknown
- 1975-07-04 IT IT25134/75A patent/IT1039715B/it active
- 1975-07-04 CA CA230,796A patent/CA1068709A/en not_active Expired
- 1975-07-04 SE SE7507707A patent/SE7507707L/xx unknown
- 1975-07-04 DK DK304075A patent/DK142198C/da active
- 1975-07-04 GB GB2824975A patent/GB1454743A/en not_active Expired
- 1975-07-04 DD DD187101A patent/DD122774A5/xx unknown
- 1975-07-04 ZM ZM86/75A patent/ZM8675A1/xx unknown
- 1975-07-04 IE IE1484/75A patent/IE41486B1/en unknown
- 1975-07-04 AT AT515775A patent/AT347742B/de not_active IP Right Cessation
- 1975-07-04 TR TR18212A patent/TR18212A/xx unknown
- 1975-07-05 JP JP50082364A patent/JPS5132736A/ja active Pending
- 1975-07-05 RO RO7582756A patent/RO72908A/ro unknown
- 1975-07-07 CS CS754810A patent/CS188229B2/cs unknown
- 1975-07-07 FR FR7521218A patent/FR2277085A1/fr active Granted
- 1975-07-07 BE BE158055A patent/BE831085A/xx unknown
-
1978
- 1978-11-15 KE KE2902A patent/KE2902A/xx unknown
- 1978-12-14 HK HK738/78A patent/HK73878A/xx unknown
- 1978-12-30 MY MY483/78A patent/MY7800483A/xx unknown
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