CH563117A5 - Biocidal triazolylphosphorus cpds - by reaction of hydroxytriazoles and organophosphorus cpds - Google Patents
Biocidal triazolylphosphorus cpds - by reaction of hydroxytriazoles and organophosphorus cpdsInfo
- Publication number
- CH563117A5 CH563117A5 CH1806471A CH1806471A CH563117A5 CH 563117 A5 CH563117 A5 CH 563117A5 CH 1806471 A CH1806471 A CH 1806471A CH 1806471 A CH1806471 A CH 1806471A CH 563117 A5 CH563117 A5 CH 563117A5
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- larvae
- test
- formula
- ch3s
- Prior art date
Links
- 230000003115 biocidal effect Effects 0.000 title abstract description 3
- QEASJVYPHMYPJM-UHFFFAOYSA-N 1,2-dihydrotriazol-5-one Chemical class OC1=CNN=N1 QEASJVYPHMYPJM-UHFFFAOYSA-N 0.000 title description 4
- 238000006243 chemical reaction Methods 0.000 title description 3
- -1 phenylthio, phenylsulphinyl Chemical group 0.000 claims abstract description 40
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 8
- 241001465754 Metazoa Species 0.000 claims abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims abstract description 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 4
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 47
- 239000004480 active ingredient Substances 0.000 claims description 37
- 238000012360 testing method Methods 0.000 claims description 30
- 239000000203 mixture Substances 0.000 claims description 24
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
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- 230000000694 effects Effects 0.000 claims description 15
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- 238000002474 experimental method Methods 0.000 claims description 8
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- 231100000614 poison Toxicity 0.000 claims description 6
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- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 238000004587 chromatography analysis Methods 0.000 claims description 3
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- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 3
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- FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 claims description 2
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- 230000001418 larval effect Effects 0.000 claims description 2
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- 125000000217 alkyl group Chemical group 0.000 abstract description 7
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- 150000007529 inorganic bases Chemical class 0.000 abstract description 2
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- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 74
- QSLPNSWXUQHVLP-UHFFFAOYSA-N $l^{1}-sulfanylmethane Chemical compound [S]C QSLPNSWXUQHVLP-UHFFFAOYSA-N 0.000 description 64
- 125000000134 2-(methylsulfanyl)ethyl group Chemical group [H]C([H])([H])SC([H])([H])C([H])([H])[*] 0.000 description 62
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 53
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 30
- 238000002844 melting Methods 0.000 description 19
- 230000008018 melting Effects 0.000 description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 19
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 150000003839 salts Chemical class 0.000 description 14
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 13
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 12
- BZQFBWGGLXLEPQ-REOHCLBHSA-N phosphoserine Chemical compound OC(=O)[C@@H](N)COP(O)(O)=O BZQFBWGGLXLEPQ-REOHCLBHSA-N 0.000 description 12
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- KMJJJTCKNZYTEY-UHFFFAOYSA-N chloro-diethoxy-sulfanylidene-$l^{5}-phosphane Chemical compound CCOP(Cl)(=S)OCC KMJJJTCKNZYTEY-UHFFFAOYSA-N 0.000 description 9
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 7
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- 239000013078 crystal Substances 0.000 description 6
- 235000011181 potassium carbonates Nutrition 0.000 description 6
- OSZLIAQSASUALS-UHFFFAOYSA-N 3-methylsulfanyl-2-phenyl-1h-1,2,4-triazol-5-one Chemical compound CSC1=NC(=O)NN1C1=CC=CC=C1 OSZLIAQSASUALS-UHFFFAOYSA-N 0.000 description 5
- 239000005995 Aluminium silicate Substances 0.000 description 5
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- 235000012211 aluminium silicate Nutrition 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 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 5
- 235000015320 potassium carbonate Nutrition 0.000 description 5
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
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- ZPVFNVKXPPDEOU-UHFFFAOYSA-N 3-chloro-2-propan-2-yl-1h-1,2,4-triazol-5-one Chemical compound CC(C)N1NC(=O)N=C1Cl ZPVFNVKXPPDEOU-UHFFFAOYSA-N 0.000 description 3
- WRJOIKFTCSTNRQ-UHFFFAOYSA-N 3-methoxy-2-propan-2-yl-1h-1,2,4-triazol-5-one Chemical compound COC1=NC(O)=NN1C(C)C WRJOIKFTCSTNRQ-UHFFFAOYSA-N 0.000 description 3
- GPLIEVZOSLZRMR-UHFFFAOYSA-N 3-methylsulfanyl-2-propan-2-yl-1h-1,2,4-triazol-5-one Chemical compound CSC1=NC(O)=NN1C(C)C GPLIEVZOSLZRMR-UHFFFAOYSA-N 0.000 description 3
- SFRLYQQHNWHCRF-UHFFFAOYSA-N 3-methylsulfinyl-2-phenyl-1h-1,2,4-triazol-5-one Chemical compound CS(=O)C1=NC(O)=NN1C1=CC=CC=C1 SFRLYQQHNWHCRF-UHFFFAOYSA-N 0.000 description 3
- SJJHQFDTFKPOSJ-UHFFFAOYSA-N 3-methylsulfonyl-2-phenyl-1h-1,2,4-triazol-5-one Chemical compound CS(=O)(=O)C1=NC(O)=NN1C1=CC=CC=C1 SJJHQFDTFKPOSJ-UHFFFAOYSA-N 0.000 description 3
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- 241000238660 Blattidae Species 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 241000907223 Bruchinae Species 0.000 description 1
- HZBFWRKXQNPMER-UHFFFAOYSA-N C(C)P(=S)(Cl)[ClH]CC Chemical compound C(C)P(=S)(Cl)[ClH]CC HZBFWRKXQNPMER-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241001414835 Cimicidae Species 0.000 description 1
- 241000256113 Culicidae Species 0.000 description 1
- 241000254171 Curculionidae Species 0.000 description 1
- 241001466044 Delphacidae Species 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical compound NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 description 1
- 241000238816 Gryllidae Species 0.000 description 1
- 241001243087 Gryllotalpidae Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241001124557 Lymantriidae Species 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 241000257226 Muscidae Species 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- 241000256259 Noctuidae Species 0.000 description 1
- 241000233654 Oomycetes Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 241000255893 Pyralidae Species 0.000 description 1
- 241001124072 Reduviidae Species 0.000 description 1
- 241000254062 Scarabaeidae Species 0.000 description 1
- 101100073357 Streptomyces halstedii sch2 gene Proteins 0.000 description 1
- 241000254107 Tenebrionidae Species 0.000 description 1
- 241000255588 Tephritidae Species 0.000 description 1
- 241000896028 Tettigoniidae Species 0.000 description 1
- 241000130767 Tineidae Species 0.000 description 1
- 241000131339 Tipulidae Species 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- DNEHKUCSURWDGO-UHFFFAOYSA-N aluminum sodium Chemical compound [Na].[Al] DNEHKUCSURWDGO-UHFFFAOYSA-N 0.000 description 1
- 230000000507 anthelmentic effect Effects 0.000 description 1
- 239000000921 anthelmintic agent Substances 0.000 description 1
- 229940124339 anthelmintic agent Drugs 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229920005551 calcium lignosulfonate Polymers 0.000 description 1
- RYAGRZNBULDMBW-UHFFFAOYSA-L calcium;3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Ca+2].COC1=CC=CC(CC(CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O RYAGRZNBULDMBW-UHFFFAOYSA-L 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- XFBJRFNXPUCPKU-UHFFFAOYSA-N chloro-dimethoxy-sulfanylidene-$l^{5}-phosphane Chemical compound COP(Cl)(=S)OC XFBJRFNXPUCPKU-UHFFFAOYSA-N 0.000 description 1
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- PFRQPEFBPFBASI-UHFFFAOYSA-N ethoxy-hydroxy-propylsulfanyl-sulfanylidene-$l^{5}-phosphane Chemical compound CCCSP(O)(=S)OCC PFRQPEFBPFBASI-UHFFFAOYSA-N 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000002464 fungitoxic effect Effects 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003750 molluscacide Substances 0.000 description 1
- 230000002013 molluscicidal effect Effects 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- RBXVOQPAMPBADW-UHFFFAOYSA-N nitrous acid;phenol Chemical class ON=O.OC1=CC=CC=C1 RBXVOQPAMPBADW-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000000286 phenylethyl group Chemical class [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
- 229940067157 phenylhydrazine Drugs 0.000 description 1
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 1
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- KZOJQMWTKJDSQJ-UHFFFAOYSA-M sodium;2,3-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 KZOJQMWTKJDSQJ-UHFFFAOYSA-M 0.000 description 1
- SRAWNDFHGTVUNZ-UHFFFAOYSA-M sodium;3,6-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC(CCCC)=CC2=CC(CCCC)=CC=C21 SRAWNDFHGTVUNZ-UHFFFAOYSA-M 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/12—Oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having three nitrogen atoms as the only ring hetero atoms
- C07F9/6518—Five-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (55)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE792450D BE792450A (fr) | 1971-12-10 | Composes organophosphores et produits pesticides qui en contiennent | |
| BE792451D BE792451A (fr) | 1971-12-10 | Esters triazolyliques d'acides phosphores et produits pesticides qui encontiennent | |
| BE792449D BE792449A (fr) | 1971-12-10 | Esters triazolyliques d'acides oxygenes du phosphore et produits pesticides qui en renferment | |
| CH1806471A CH563117A5 (en) | 1971-12-10 | 1971-12-10 | Biocidal triazolylphosphorus cpds - by reaction of hydroxytriazoles and organophosphorus cpds |
| AU48961/72A AU480275B2 (en) | 1971-12-10 | 1972-11-16 | Triazolylphosphorus compounds and their use for pest control |
| CA156,940A CA1045630A (en) | 1971-12-10 | 1972-11-20 | Triazolylphosphorus compounds |
| CA156,938A CA967578A (en) | 1971-12-10 | 1972-11-20 | Esters |
| CA156,939A CA1026346A (en) | 1971-12-10 | 1972-11-20 | Triazolyphosphorus compounds |
| IL40871A IL40871A (en) | 1971-12-10 | 1972-11-20 | Triazolylphosphorus compounds,their production and their use for pest control |
| IL40874A IL40874A (en) | 1971-12-10 | 1972-11-20 | Triazolylphosphorus compounds,their production and their use for pest control |
| IL40872A IL40872A (en) | 1971-12-10 | 1972-11-20 | Triazolylphosphorus compounds,their production and their use for pest control |
| US310728A US3867398A (en) | 1971-12-10 | 1972-11-30 | Triazolyl phosphorus compounds |
| US310727A US3867397A (en) | 1971-12-10 | 1972-11-30 | Triazolyl phosphorus compounds |
| PH14137A PH10707A (en) | 1971-12-10 | 1972-12-01 | Triazolyl phosphors compounds |
| EG501/72A EG10848A (en) | 1971-12-10 | 1972-12-05 | New esters of triazolylphosphorus,their use as insecticides |
| BG022051A BG22785A3 (bg) | 1971-12-10 | 1972-12-06 | Инсектицидно и акарицидно средство |
| DE2259983A DE2259983A1 (de) | 1971-12-10 | 1972-12-07 | Neue ester |
| AT1042472A AT318303B (de) | 1971-12-10 | 1972-12-07 | Schädlingsbekämpfungsmittel |
| DE2259960A DE2259960C2 (de) | 1971-12-10 | 1972-12-07 | 1.2.4-Triazolyl-(thiono)-phosphor(phosphon)-säureester, Verfahren zu ihrer Herstellung und diese enthaltende Schädlingsbekämpfungsmittel |
| OA54772A OA04230A (fr) | 1971-12-10 | 1972-12-07 | Esters triazolyliques d'acides oxygénés du phosphore et produits pesticides qui en renferment. |
| AT1042272A AT316214B (de) | 1971-12-10 | 1972-12-07 | Schädlingsbekämpfungsmittel |
| IT7232671A IT983182B (it) | 1971-12-10 | 1972-12-07 | Triazolil fosforo derivati procedi mento per la loro preparazione e relative composizioni per combatte re organismi nocivi |
| TR17149A TR17149A (tr) | 1971-12-10 | 1972-12-07 | Yeni esterler |
| NL7216637A NL7216637A (OSRAM) | 1971-12-10 | 1972-12-07 | |
| NL7216627A NL7216627A (OSRAM) | 1971-12-10 | 1972-12-07 | |
| DE2259974A DE2259974A1 (de) | 1971-12-10 | 1972-12-07 | Neue ester |
| AT1042372A AT314904B (de) | 1971-12-10 | 1972-12-07 | Schädlingsbekämpfungsmittel |
| AR245527A AR210235A1 (es) | 1971-12-10 | 1972-12-07 | Nuevos derivados 124-triaxolil 5-sustuidos de 3-(00-dialquil,o,sdialquilo o,alquil,alquil fosfato,tiofosfato,fosfonato otiofosfonato utiles como pesticidas,menos para su uso farmaceutico oveterinario,procedimiento para su preparacion ycomposiciones que los contienen |
| NL7216636A NL7216636A (OSRAM) | 1971-12-10 | 1972-12-07 | |
| IT7232672A IT983183B (it) | 1971-12-10 | 1972-12-07 | Composti triazolil fosforici proce dimento per la loro preparazione e relative composizioni per combat tere organismi nocivi |
| IT32670/72A IT983181B (it) | 1971-12-10 | 1972-12-07 | Composti triazolil fosforici pro cedimento per la loro preparazio ne e relative composizioni per combattere organismi nocivi |
| HUCI1316A HU165795B (OSRAM) | 1971-12-10 | 1972-12-08 | |
| SU721855102A SU603318A3 (ru) | 1971-12-10 | 1972-12-08 | Средство борьбы с насекомыми,клещами и нематодами |
| SU721855798A SU673140A3 (ru) | 1971-12-10 | 1972-12-08 | Инсектоакарицидное средство |
| FR7243757A FR2162590B1 (OSRAM) | 1971-12-10 | 1972-12-08 | |
| DD167404A DD103796A5 (OSRAM) | 1971-12-10 | 1972-12-08 | |
| HUCI1314A HU167245B (OSRAM) | 1971-12-10 | 1972-12-08 | |
| HUCI1315A HU166377B (OSRAM) | 1971-12-10 | 1972-12-08 | |
| DD167397A DD104182A5 (OSRAM) | 1971-12-10 | 1972-12-08 | |
| GB5681672A GB1409574A (en) | 1971-12-10 | 1972-12-08 | Triazolyl phosphorus esters having pesticidal properties |
| GB5681572A GB1417723A (en) | 1971-12-10 | 1972-12-08 | Phosphorus-containing ester derivatives of hydroxytriazoles |
| CS8438A CS169831B2 (OSRAM) | 1971-12-10 | 1972-12-08 | |
| FR7243758A FR2162591B1 (OSRAM) | 1971-12-10 | 1972-12-08 | |
| GB5681772A GB1420328A (en) | 1971-12-10 | 1972-12-08 | Triazolyl phosphorus esters having pesticidal properties |
| ZA728704A ZA728704B (en) | 1971-12-10 | 1972-12-08 | New esters |
| FR7243756A FR2162589B1 (OSRAM) | 1971-12-10 | 1972-12-08 | |
| CS8439A CS169832B2 (OSRAM) | 1971-12-10 | 1972-12-08 | |
| CS8440A CS172962B2 (OSRAM) | 1971-12-10 | 1972-12-08 | |
| ES409487A ES409487A1 (es) | 1971-12-10 | 1972-12-09 | Procedimiento para la preparacion de compuestos triazoli- fosforicos. |
| JP47123873A JPS6011011B2 (ja) | 1971-12-10 | 1972-12-09 | 有害生物防除剤及びその製造方法 |
| JP47123874A JPS4862943A (OSRAM) | 1971-12-10 | 1972-12-09 | |
| JP47123875A JPS4862944A (OSRAM) | 1971-12-10 | 1972-12-09 | |
| US05/530,461 US3932630A (en) | 1971-12-10 | 1974-12-06 | Triazolyl phosphorus esters as pesticides |
| US05/614,733 US4044124A (en) | 1971-12-10 | 1975-09-18 | Triazolylphosphorus compounds |
| MY97/79A MY7900097A (en) | 1971-12-10 | 1979-12-30 | Phosphorus-containing ester derivatives of hydroxytriazoles |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1806471A CH563117A5 (en) | 1971-12-10 | 1971-12-10 | Biocidal triazolylphosphorus cpds - by reaction of hydroxytriazoles and organophosphorus cpds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH563117A5 true CH563117A5 (en) | 1975-06-30 |
Family
ID=4430171
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1806471A CH563117A5 (en) | 1971-12-10 | 1971-12-10 | Biocidal triazolylphosphorus cpds - by reaction of hydroxytriazoles and organophosphorus cpds |
Country Status (9)
| Country | Link |
|---|---|
| AT (1) | AT314904B (OSRAM) |
| BG (1) | BG22785A3 (OSRAM) |
| CH (1) | CH563117A5 (OSRAM) |
| CS (3) | CS169831B2 (OSRAM) |
| ES (1) | ES409487A1 (OSRAM) |
| HU (2) | HU167245B (OSRAM) |
| SU (2) | SU603318A3 (OSRAM) |
| TR (1) | TR17149A (OSRAM) |
| ZA (1) | ZA728704B (OSRAM) |
-
1971
- 1971-12-10 CH CH1806471A patent/CH563117A5/de not_active IP Right Cessation
-
1972
- 1972-12-06 BG BG022051A patent/BG22785A3/xx unknown
- 1972-12-07 TR TR17149A patent/TR17149A/xx unknown
- 1972-12-07 AT AT1042372A patent/AT314904B/de not_active IP Right Cessation
- 1972-12-08 HU HUCI1314A patent/HU167245B/hu unknown
- 1972-12-08 ZA ZA728704A patent/ZA728704B/xx unknown
- 1972-12-08 HU HUCI1316A patent/HU165795B/hu unknown
- 1972-12-08 CS CS8438A patent/CS169831B2/cs unknown
- 1972-12-08 CS CS8440A patent/CS172962B2/cs unknown
- 1972-12-08 SU SU721855102A patent/SU603318A3/ru active
- 1972-12-08 CS CS8439A patent/CS169832B2/cs unknown
- 1972-12-08 SU SU721855798A patent/SU673140A3/ru active
- 1972-12-09 ES ES409487A patent/ES409487A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CS169831B2 (OSRAM) | 1976-07-29 |
| BG22785A3 (bg) | 1977-04-20 |
| ZA728704B (en) | 1973-07-25 |
| HU165795B (OSRAM) | 1974-11-28 |
| SU673140A3 (ru) | 1979-07-05 |
| CS172962B2 (OSRAM) | 1977-01-28 |
| SU603318A3 (ru) | 1978-04-15 |
| CS169832B2 (OSRAM) | 1976-07-29 |
| TR17149A (tr) | 1974-04-25 |
| HU167245B (OSRAM) | 1975-09-27 |
| ES409487A1 (es) | 1976-04-01 |
| AT314904B (de) | 1974-04-25 |
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