JPH0245618B2 - - Google Patents
Info
- Publication number
- JPH0245618B2 JPH0245618B2 JP56150497A JP15049781A JPH0245618B2 JP H0245618 B2 JPH0245618 B2 JP H0245618B2 JP 56150497 A JP56150497 A JP 56150497A JP 15049781 A JP15049781 A JP 15049781A JP H0245618 B2 JPH0245618 B2 JP H0245618B2
- Authority
- JP
- Japan
- Prior art keywords
- ethyl
- methyl
- phenoxy
- carbamate
- methylcarbamate
- 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 - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 claims description 74
- -1 ethyl 2-[p-(p-fluorophenoxy)phenoxy]propyl Chemical group 0.000 claims description 54
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 claims description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims description 34
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 33
- 239000001257 hydrogen Substances 0.000 claims description 32
- 239000000203 mixture Substances 0.000 claims description 31
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 19
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- 150000002367 halogens Chemical class 0.000 claims description 17
- 150000002431 hydrogen Chemical class 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- 239000012876 carrier material Substances 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- YNTOKMNHRPSGFU-UHFFFAOYSA-N n-Propyl carbamate Chemical compound CCCOC(N)=O YNTOKMNHRPSGFU-UHFFFAOYSA-N 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
- OYUQOPHYKNQISQ-UHFFFAOYSA-N ethyl n-[2-[4-(3,5-dichlorophenoxy)phenoxy]ethyl]-n-methylcarbamate Chemical compound C1=CC(OCCN(C)C(=O)OCC)=CC=C1OC1=CC(Cl)=CC(Cl)=C1 OYUQOPHYKNQISQ-UHFFFAOYSA-N 0.000 claims description 3
- DPFDNJCEPOFAKL-UHFFFAOYSA-N ethyl n-[2-[4-(4-fluorophenoxy)phenoxy]ethyl]-n-methylcarbamate Chemical compound C1=CC(OCCN(C)C(=O)OCC)=CC=C1OC1=CC=C(F)C=C1 DPFDNJCEPOFAKL-UHFFFAOYSA-N 0.000 claims description 3
- ALUUIWAPTJRPQV-UHFFFAOYSA-N ethyl n-methyl-n-[2-(4-phenoxyphenoxy)ethyl]carbamate Chemical compound C1=CC(OCCN(C)C(=O)OCC)=CC=C1OC1=CC=CC=C1 ALUUIWAPTJRPQV-UHFFFAOYSA-N 0.000 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- QSXFDLABPQCEBQ-UHFFFAOYSA-N ethyl n-[2-(4-benzylphenoxy)propyl]carbamate Chemical compound C1=CC(OC(C)CNC(=O)OCC)=CC=C1CC1=CC=CC=C1 QSXFDLABPQCEBQ-UHFFFAOYSA-N 0.000 claims description 2
- TVSAKJCIIHYSSY-UHFFFAOYSA-N ethyl n-[2-[4-(2-fluorophenoxy)phenoxy]ethyl]-n-methylcarbamate Chemical compound C1=CC(OCCN(C)C(=O)OCC)=CC=C1OC1=CC=CC=C1F TVSAKJCIIHYSSY-UHFFFAOYSA-N 0.000 claims description 2
- OFGAFZRAAARIQN-UHFFFAOYSA-N ethyl n-methyl-n-[2-[4-(3-nitrophenoxy)phenoxy]ethyl]carbamate Chemical compound C1=CC(OCCN(C)C(=O)OCC)=CC=C1OC1=CC=CC([N+]([O-])=O)=C1 OFGAFZRAAARIQN-UHFFFAOYSA-N 0.000 claims description 2
- XPCQRDVDZPYCEO-UHFFFAOYSA-N s-ethyl n-methyl-n-[2-(4-phenoxyphenoxy)ethyl]carbamothioate Chemical compound C1=CC(OCCN(C)C(=O)SCC)=CC=C1OC1=CC=CC=C1 XPCQRDVDZPYCEO-UHFFFAOYSA-N 0.000 claims description 2
- YSWDEVNKRZTYQZ-UHFFFAOYSA-N C1=CC(OCCN(C)C(=O)OCC)=CC=C1OC1=CC(Cl)=CC=C1C Chemical compound C1=CC(OCCN(C)C(=O)OCC)=CC=C1OC1=CC(Cl)=CC=C1C YSWDEVNKRZTYQZ-UHFFFAOYSA-N 0.000 claims 1
- UXKQFXIPMZYKKH-UHFFFAOYSA-N ethyl n-[2-[4-(3-fluorophenoxy)phenoxy]ethyl]-n-methylcarbamate Chemical compound C1=CC(OCCN(C)C(=O)OCC)=CC=C1OC1=CC=CC(F)=C1 UXKQFXIPMZYKKH-UHFFFAOYSA-N 0.000 claims 1
- ZCDCAOSQFJWUJV-UHFFFAOYSA-N ethyl n-[2-[4-(3-nitrophenoxy)phenoxy]propyl]carbamate Chemical compound C1=CC(OC(C)CNC(=O)OCC)=CC=C1OC1=CC=CC([N+]([O-])=O)=C1 ZCDCAOSQFJWUJV-UHFFFAOYSA-N 0.000 claims 1
- GNKDINGSDUZNOU-UHFFFAOYSA-N ethyl n-[2-[4-[(4-chlorophenyl)methyl]phenoxy]ethyl]-n-methylcarbamate Chemical compound C1=CC(OCCN(C)C(=O)OCC)=CC=C1CC1=CC=C(Cl)C=C1 GNKDINGSDUZNOU-UHFFFAOYSA-N 0.000 claims 1
- YJAWTZOTZMCVMU-UHFFFAOYSA-N ethyl n-methyl-n-[2-[4-(3-methylphenoxy)phenoxy]ethyl]carbamate Chemical compound C1=CC(OCCN(C)C(=O)OCC)=CC=C1OC1=CC=CC(C)=C1 YJAWTZOTZMCVMU-UHFFFAOYSA-N 0.000 claims 1
- NKOBTXJYUJYFIH-UHFFFAOYSA-N ethyl n-methyl-n-[2-[4-(4-nitrophenoxy)phenoxy]ethyl]carbamate Chemical compound C1=CC(OCCN(C)C(=O)OCC)=CC=C1OC1=CC=C([N+]([O-])=O)C=C1 NKOBTXJYUJYFIH-UHFFFAOYSA-N 0.000 claims 1
- HHIQZQQZNFMPGW-UHFFFAOYSA-N methyl n-[2-(4-phenoxyphenoxy)propyl]carbamate Chemical compound C1=CC(OC(C)CNC(=O)OC)=CC=C1OC1=CC=CC=C1 HHIQZQQZNFMPGW-UHFFFAOYSA-N 0.000 claims 1
- XFCKYGSNYZDWJE-UHFFFAOYSA-N propan-2-yl n-[2-(4-benzoylphenoxy)ethyl]-n-methylcarbamate Chemical compound C1=CC(OCCN(C)C(=O)OC(C)C)=CC=C1C(=O)C1=CC=CC=C1 XFCKYGSNYZDWJE-UHFFFAOYSA-N 0.000 claims 1
- OJRHAUSLVRVYNR-UHFFFAOYSA-N propan-2-yl n-[2-(4-phenoxyphenoxy)propyl]carbamate Chemical compound C1=CC(OC(C)CNC(=O)OC(C)C)=CC=C1OC1=CC=CC=C1 OJRHAUSLVRVYNR-UHFFFAOYSA-N 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 71
- 238000012360 testing method Methods 0.000 description 55
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- 239000000243 solution Substances 0.000 description 27
- 239000013543 active substance Substances 0.000 description 25
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- ZSBDGXGICLIJGD-UHFFFAOYSA-N 4-phenoxyphenol Chemical compound C1=CC(O)=CC=C1OC1=CC=CC=C1 ZSBDGXGICLIJGD-UHFFFAOYSA-N 0.000 description 20
- 230000000694 effects Effects 0.000 description 20
- 241000607479 Yersinia pestis Species 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- KQXIITSXVXNHJX-UHFFFAOYSA-N ethyl n-(2-chloroethyl)-n-methylcarbamate Chemical compound CCOC(=O)N(C)CCCl KQXIITSXVXNHJX-UHFFFAOYSA-N 0.000 description 15
- 241000255925 Diptera Species 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 241001454293 Tetranychus urticae Species 0.000 description 12
- 239000002904 solvent Substances 0.000 description 11
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 235000013601 eggs Nutrition 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- 239000008187 granular material Substances 0.000 description 8
- 239000007921 spray Substances 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 7
- 241000257159 Musca domestica Species 0.000 description 7
- 235000013305 food Nutrition 0.000 description 7
- NPFYZDNDJHZQKY-UHFFFAOYSA-N 4-Hydroxybenzophenone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=CC=C1 NPFYZDNDJHZQKY-UHFFFAOYSA-N 0.000 description 6
- 241000238631 Hexapoda Species 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 6
- 244000046052 Phaseolus vulgaris Species 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 230000004083 survival effect Effects 0.000 description 6
- 241000254173 Coleoptera Species 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 5
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 239000003995 emulsifying agent Substances 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- QJPJQTDYNZXKQF-UHFFFAOYSA-N 4-bromoanisole Chemical compound COC1=CC=C(Br)C=C1 QJPJQTDYNZXKQF-UHFFFAOYSA-N 0.000 description 4
- 241000258937 Hemiptera Species 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- 241000258916 Leptinotarsa decemlineata Species 0.000 description 4
- 235000013339 cereals Nutrition 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 235000013312 flour Nutrition 0.000 description 4
- 230000001418 larval effect Effects 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- SXSZFJUGNJWCNB-UHFFFAOYSA-N 1-(ethoxycarbonylamino)propan-2-yl methanesulfonate Chemical compound CCOC(=O)NCC(C)OS(C)(=O)=O SXSZFJUGNJWCNB-UHFFFAOYSA-N 0.000 description 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
- XQVUQRPTZAUIOS-UHFFFAOYSA-N 4-(3-bromophenoxy)phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=CC(Br)=C1 XQVUQRPTZAUIOS-UHFFFAOYSA-N 0.000 description 3
- WEOZCKPNKHGSOI-UHFFFAOYSA-N 4-(3-fluorophenoxy)phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=CC(F)=C1 WEOZCKPNKHGSOI-UHFFFAOYSA-N 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 241000526145 Psylla Species 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 241000018137 Trialeurodes vaporariorum Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 241000209140 Triticum Species 0.000 description 3
- 235000021307 Triticum Nutrition 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 235000015895 biscuits Nutrition 0.000 description 3
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 239000004495 emulsifiable concentrate Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 229920001821 foam rubber Polymers 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000008262 pumice Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- NCTBMVAIKUNJFJ-UHFFFAOYSA-N 1-methoxy-4-(3-methylphenoxy)benzene Chemical compound C1=CC(OC)=CC=C1OC1=CC=CC(C)=C1 NCTBMVAIKUNJFJ-UHFFFAOYSA-N 0.000 description 2
- KEJZOGAPCBDGBF-UHFFFAOYSA-N 3-methyl-4-phenoxyphenol Chemical compound CC1=CC(O)=CC=C1OC1=CC=CC=C1 KEJZOGAPCBDGBF-UHFFFAOYSA-N 0.000 description 2
- BNMNQSSEFSCQJH-UHFFFAOYSA-N 4-(3-methylphenoxy)phenol Chemical compound CC1=CC=CC(OC=2C=CC(O)=CC=2)=C1 BNMNQSSEFSCQJH-UHFFFAOYSA-N 0.000 description 2
- PNRWPTBVLWWBCW-UHFFFAOYSA-N 4-(5-chloro-2-methylphenoxy)phenol Chemical compound CC1=CC=C(Cl)C=C1OC1=CC=C(O)C=C1 PNRWPTBVLWWBCW-UHFFFAOYSA-N 0.000 description 2
- QBUZGHPDFUNKIZ-UHFFFAOYSA-N 4-[3-(trifluoromethyl)phenoxy]phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=CC(C(F)(F)F)=C1 QBUZGHPDFUNKIZ-UHFFFAOYSA-N 0.000 description 2
- HJSPWKGEPDZNLK-UHFFFAOYSA-N 4-benzylphenol Chemical compound C1=CC(O)=CC=C1CC1=CC=CC=C1 HJSPWKGEPDZNLK-UHFFFAOYSA-N 0.000 description 2
- 241000238876 Acari Species 0.000 description 2
- 241000175828 Adoxophyes orana Species 0.000 description 2
- 241000256118 Aedes aegypti Species 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- 241001600407 Aphis <genus> Species 0.000 description 2
- 241001425390 Aphis fabae Species 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000238657 Blattella germanica Species 0.000 description 2
- 241001465977 Coccoidea Species 0.000 description 2
- 241000256059 Culex pipiens Species 0.000 description 2
- 241000256602 Isoptera Species 0.000 description 2
- 241000406668 Loxodonta cyclotis Species 0.000 description 2
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 241000244206 Nematoda Species 0.000 description 2
- 241001491877 Operophtera brumata Species 0.000 description 2
- 241000238814 Orthoptera Species 0.000 description 2
- 241000048273 Periplaneta japonica Species 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 241000318997 Rhyzopertha dominica Species 0.000 description 2
- 241000254179 Sitophilus granarius Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 241000254113 Tribolium castaneum Species 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 239000003849 aromatic solvent Substances 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 239000004067 bulking agent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
- OIOAWVCIKNVYKR-UHFFFAOYSA-N ethyl n-[2-[4-(3-bromophenoxy)phenoxy]ethyl]-n-methylcarbamate Chemical compound C1=CC(OCCN(C)C(=O)OCC)=CC=C1OC1=CC=CC(Br)=C1 OIOAWVCIKNVYKR-UHFFFAOYSA-N 0.000 description 2
- VAMUBMXKZDWUKN-UHFFFAOYSA-N ethyl n-butyl-n-(2-hydroxyethyl)carbamate Chemical compound CCCCN(CCO)C(=O)OCC VAMUBMXKZDWUKN-UHFFFAOYSA-N 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
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- GPAFVMVMCVTSPO-UHFFFAOYSA-N propan-2-yl n-(2-chloroethyl)-n-methylcarbamate Chemical compound CC(C)OC(=O)N(C)CCCl GPAFVMVMCVTSPO-UHFFFAOYSA-N 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000375 suspending agent 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/257—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings
- C07C43/29—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings containing halogen
-
- 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
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
- C07C205/35—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/36—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
- C07C205/38—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the oxygen atom of at least one of the etherified hydroxy groups being further bound to a carbon atom of a six-membered aromatic ring, e.g. nitrodiphenyl ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/257—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings
- C07C43/263—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings the aromatic rings being non-condensed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/257—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings
- C07C43/295—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings containing hydroxy or O-metal groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH712080A CH645345A5 (en) | 1980-09-23 | 1980-09-23 | Carbamic acid derivatives and their use as pesticides |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS5785354A JPS5785354A (en) | 1982-05-28 |
JPH0245618B2 true JPH0245618B2 (enrdf_load_stackoverflow) | 1990-10-11 |
Family
ID=4320277
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP56150497A Granted JPS5785354A (en) | 1980-09-23 | 1981-09-22 | Carbamic acid derivative |
Country Status (3)
Country | Link |
---|---|
JP (1) | JPS5785354A (enrdf_load_stackoverflow) |
CH (1) | CH645345A5 (enrdf_load_stackoverflow) |
ZA (1) | ZA816446B (enrdf_load_stackoverflow) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4660034A (en) * | 1984-12-03 | 1987-04-21 | Toshinobu Futagawa | Information input machine |
-
1980
- 1980-09-23 CH CH712080A patent/CH645345A5/de not_active IP Right Cessation
-
1981
- 1981-09-16 ZA ZA816446A patent/ZA816446B/xx unknown
- 1981-09-22 JP JP56150497A patent/JPS5785354A/ja active Granted
Also Published As
Publication number | Publication date |
---|---|
CH645345A5 (en) | 1984-09-28 |
JPS5785354A (en) | 1982-05-28 |
ZA816446B (en) | 1982-09-29 |
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