IL34985A - Triazolothiazole esters of phosphoric, phosphonic and phosphonic acids and of the appropriate tionic acids, their preparation and use as insecticides and acaricides - Google Patents
Triazolothiazole esters of phosphoric, phosphonic and phosphonic acids and of the appropriate tionic acids, their preparation and use as insecticides and acaricidesInfo
- Publication number
- IL34985A IL34985A IL34985A IL3498570A IL34985A IL 34985 A IL34985 A IL 34985A IL 34985 A IL34985 A IL 34985A IL 3498570 A IL3498570 A IL 3498570A IL 34985 A IL34985 A IL 34985A
- Authority
- IL
- Israel
- Prior art keywords
- ester
- formula
- esters
- stands
- active compound
- Prior art date
Links
- 150000002148 esters Chemical class 0.000 title claims description 29
- 239000002253 acid Substances 0.000 title claims description 26
- 230000000895 acaricidal effect Effects 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title description 11
- 150000007513 acids Chemical class 0.000 title description 10
- 239000002917 insecticide Substances 0.000 title description 3
- 239000000642 acaricide Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 49
- 238000000034 method Methods 0.000 claims description 19
- -1 heterocyclic amine Chemical class 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 14
- 241000238631 Hexapoda Species 0.000 claims description 12
- 239000003085 diluting agent Substances 0.000 claims description 12
- 230000006378 damage Effects 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 7
- 230000000749 insecticidal effect Effects 0.000 claims description 6
- 150000004820 halides Chemical class 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 239000004094 surface-active agent Substances 0.000 claims description 3
- HAMDSFMMUATQLI-UHFFFAOYSA-N 5h-[1,3]thiazolo[4,5-d]triazol-5-ol Chemical compound N1=NC2=NC(O)SC2=N1 HAMDSFMMUATQLI-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims 1
- 150000008041 alkali metal carbonates Chemical group 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical group 0.000 claims 1
- 239000003701 inert diluent Substances 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 239000003995 emulsifying agent Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 241000238876 Acari Species 0.000 description 8
- 241000255925 Diptera Species 0.000 description 8
- 241000254173 Coleoptera Species 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 241000500437 Plutella xylostella Species 0.000 description 5
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- 239000007858 starting material Substances 0.000 description 5
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- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 4
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- 238000009472 formulation Methods 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000257159 Musca domestica Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
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- 241000500439 Plutella Species 0.000 description 3
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 230000000361 pesticidal effect Effects 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
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- 235000011302 Brassica oleracea Nutrition 0.000 description 2
- 241000257163 Calliphora vicina Species 0.000 description 2
- 241000255579 Ceratitis capitata Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241001327638 Cimex lectularius Species 0.000 description 2
- 241000256059 Culex pipiens Species 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 241001581006 Dysaphis plantaginea Species 0.000 description 2
- 241000483001 Euproctis chrysorrhoea Species 0.000 description 2
- 239000004606 Fillers/Extenders Substances 0.000 description 2
- 241000255896 Galleria mellonella Species 0.000 description 2
- 241001251909 Hyalopterus pruni Species 0.000 description 2
- 241000257303 Hymenoptera Species 0.000 description 2
- 241000255685 Malacosoma neustria Species 0.000 description 2
- 241000254099 Melolontha melolontha Species 0.000 description 2
- 241000721623 Myzus Species 0.000 description 2
- 241000810465 Myzus cerasi cerasi Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 241001491877 Operophtera brumata Species 0.000 description 2
- 241000131101 Oryzaephilus surinamensis Species 0.000 description 2
- 241000488583 Panonychus ulmi Species 0.000 description 2
- 241000238675 Periplaneta americana Species 0.000 description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 2
- 241001396980 Phytonemus pallidus Species 0.000 description 2
- 241000255969 Pieris brassicae Species 0.000 description 2
- 241000722238 Pseudococcus maritimus Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 241000125167 Rhopalosiphum padi Species 0.000 description 2
- 241001510241 Rhyparobia Species 0.000 description 2
- 235000001537 Ribes X gardonianum Nutrition 0.000 description 2
- 235000001535 Ribes X utile Nutrition 0.000 description 2
- 235000016919 Ribes petraeum Nutrition 0.000 description 2
- 244000281247 Ribes rubrum Species 0.000 description 2
- 235000002355 Ribes spicatum Nutrition 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
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- 241001494115 Stomoxys calcitrans Species 0.000 description 2
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- 241001238451 Tortrix viridana Species 0.000 description 2
- 241000267822 Trogoderma granarium Species 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000010410 dusting Methods 0.000 description 2
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- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- OWFJMIVZYSDULZ-PXOLEDIWSA-N (4s,4ar,5s,5ar,6s,12ar)-4-(dimethylamino)-1,5,6,10,11,12a-hexahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide Chemical compound C1=CC=C2[C@](O)(C)[C@H]3[C@H](O)[C@H]4[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]4(O)C(=O)C3=C(O)C2=C1O OWFJMIVZYSDULZ-PXOLEDIWSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
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- 241001664260 Byturus tomentosus Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000254137 Cicadidae Species 0.000 description 1
- 241001415288 Coccidae Species 0.000 description 1
- 241001465977 Coccoidea Species 0.000 description 1
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- 241001641895 Dermestes Species 0.000 description 1
- 241001513837 Dermestes maculatus Species 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- 241000255581 Drosophila <fruit fly, genus> Species 0.000 description 1
- 241000255601 Drosophila melanogaster Species 0.000 description 1
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- 241000630736 Ephestia Species 0.000 description 1
- 241000122098 Ephestia kuehniella Species 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 241000239245 Euscelis Species 0.000 description 1
- 241000953886 Fannia canicularis Species 0.000 description 1
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- 241000721715 Macrosiphum Species 0.000 description 1
- 241000721714 Macrosiphum euphorbiae Species 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 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
- 241000961933 Nephotettix virescens Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
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- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
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- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 1
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- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
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- 229960000583 acetic acid Drugs 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
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- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 235000021028 berry Nutrition 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
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- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
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- YYJNOYZRYGDPNH-MFKUBSTISA-N fenpyroximate Chemical compound C=1C=C(C(=O)OC(C)(C)C)C=CC=1CO/N=C/C=1C(C)=NN(C)C=1OC1=CC=CC=C1 YYJNOYZRYGDPNH-MFKUBSTISA-N 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 238000003958 fumigation Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
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- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
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- 230000005923 long-lasting effect Effects 0.000 description 1
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- NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
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- 238000002156 mixing Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 230000001473 noxious effect Effects 0.000 description 1
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- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D277/38—Nitrogen atoms
- C07D277/40—Unsubstituted amino or imino radicals
-
- 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
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero 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)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691942015 DE1942015C3 (de) | 1969-08-19 | Triazolo-thiazol (th'iono)-phosphor (phosphon)-säureester, Verfahren zu ihrer Herstellung sowie diese enthaltende Mittel |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL34985A0 IL34985A0 (en) | 1970-09-17 |
| IL34985A true IL34985A (en) | 1972-11-28 |
Family
ID=5743135
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL34985A IL34985A (en) | 1969-08-19 | 1970-07-24 | Triazolothiazole esters of phosphoric, phosphonic and phosphonic acids and of the appropriate tionic acids, their preparation and use as insecticides and acaricides |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US3682943A (nl) |
| JP (1) | JPS553325B1 (nl) |
| AT (1) | AT296338B (nl) |
| BE (1) | BE755028A (nl) |
| CA (1) | CA938613A (nl) |
| CH (1) | CH538513A (nl) |
| CS (1) | CS164281B2 (nl) |
| DK (1) | DK126505B (nl) |
| EG (1) | EG10292A (nl) |
| ES (1) | ES382819A1 (nl) |
| FR (1) | FR2059010A5 (nl) |
| GB (1) | GB1269488A (nl) |
| IL (1) | IL34985A (nl) |
| NL (1) | NL166264C (nl) |
| PL (1) | PL80994B1 (nl) |
| RO (1) | RO62237A (nl) |
| SU (1) | SU498912A3 (nl) |
| TR (1) | TR16583A (nl) |
| ZA (1) | ZA705066B (nl) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3948926A (en) * | 1971-12-30 | 1976-04-06 | Saburo Kano | O,O-Diethyl-2-(5-ethyl-6-bromothiazolo[3,2-b]-s-triazolyl)thionophosphate |
| JPS4932873B2 (nl) * | 1971-12-30 | 1974-09-03 | ||
| US3970751A (en) * | 1972-12-29 | 1976-07-20 | Nippon Soda Company Limited | Certain thiazolotriazolyphosphonothioates used as insecticides |
| US4024252A (en) * | 1973-04-07 | 1977-05-17 | Nippon Soda Company Limited | 2-(5-Ethyl-6-bromothiazolo[3,2-b]-5-triazolyl)thiophosphonate esters, compositions and method of use |
| DE2350631C2 (de) * | 1973-10-09 | 1981-10-15 | Bayer Ag, 5090 Leverkusen | Triazolothiazol-(thiono)-phosphor(phosphon)-säureester, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Insektizide und Akarizide |
| DE2361451C2 (de) * | 1973-12-10 | 1982-06-03 | Bayer Ag, 5090 Leverkusen | Triazolothiazolyl-(thiono)-phosphor (phosphon)-säureester, Verfahren zu ihrer Herstellung sowie ihre Verwendung zur Bekämpfung von Insekten, Milben und Zecken |
| KR0168979B1 (ko) * | 1995-07-12 | 1999-01-15 | 김종인 | 티아졸릴 트리아졸로티아졸 유도체 |
| US8747875B2 (en) * | 2008-09-29 | 2014-06-10 | The Hartz Mountain Corporation | Photo-stable pest control |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3428645A (en) * | 1965-10-23 | 1969-02-18 | Stauffer Chemical Co | Phosphorus esters of certain thiazole derivatives |
-
0
- BE BE755028D patent/BE755028A/xx unknown
-
1970
- 1970-07-23 ZA ZA705066A patent/ZA705066B/xx unknown
- 1970-07-24 IL IL34985A patent/IL34985A/en unknown
- 1970-07-29 RO RO64091A patent/RO62237A/ro unknown
- 1970-07-29 CH CH1146370A patent/CH538513A/de not_active IP Right Cessation
- 1970-08-06 GB GB37989/70A patent/GB1269488A/en not_active Expired
- 1970-08-10 CS CS5552A patent/CS164281B2/cs unknown
- 1970-08-11 EG EG361/70A patent/EG10292A/xx active
- 1970-08-12 US US63271A patent/US3682943A/en not_active Expired - Lifetime
- 1970-08-12 CA CA090540A patent/CA938613A/en not_active Expired
- 1970-08-13 SU SU1470853A patent/SU498912A3/ru active
- 1970-08-17 JP JP7145570A patent/JPS553325B1/ja active Pending
- 1970-08-18 DK DK424370AA patent/DK126505B/da unknown
- 1970-08-18 TR TR16583A patent/TR16583A/xx unknown
- 1970-08-18 NL NL7012197.A patent/NL166264C/nl not_active IP Right Cessation
- 1970-08-18 PL PL1970142756A patent/PL80994B1/pl unknown
- 1970-08-18 ES ES382819A patent/ES382819A1/es not_active Expired
- 1970-08-19 AT AT751870A patent/AT296338B/de not_active IP Right Cessation
- 1970-08-19 FR FR7030520A patent/FR2059010A5/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| SU498912A3 (ru) | 1976-01-05 |
| NL7012197A (nl) | 1971-02-23 |
| GB1269488A (en) | 1972-04-06 |
| DE1942015B2 (de) | 1977-06-02 |
| DE1942015A1 (de) | 1971-03-04 |
| CH538513A (de) | 1973-06-30 |
| IL34985A0 (en) | 1970-09-17 |
| ES382819A1 (es) | 1972-11-16 |
| CS164281B2 (nl) | 1975-11-07 |
| TR16583A (tr) | 1973-01-01 |
| CA938613A (en) | 1973-12-18 |
| AT296338B (de) | 1972-02-10 |
| BE755028A (fr) | 1971-02-19 |
| JPS553325B1 (nl) | 1980-01-24 |
| EG10292A (en) | 1976-07-31 |
| FR2059010A5 (nl) | 1971-05-28 |
| ZA705066B (en) | 1971-04-28 |
| NL166264C (nl) | 1981-07-15 |
| DK126505B (da) | 1973-07-23 |
| PL80994B1 (nl) | 1975-08-30 |
| RO62237A (nl) | 1977-08-15 |
| US3682943A (en) | 1972-08-08 |
| NL166264B (nl) | 1981-02-16 |
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