CH615193A5 - - Google Patents
Download PDFInfo
- Publication number
- CH615193A5 CH615193A5 CH84275A CH84275A CH615193A5 CH 615193 A5 CH615193 A5 CH 615193A5 CH 84275 A CH84275 A CH 84275A CH 84275 A CH84275 A CH 84275A CH 615193 A5 CH615193 A5 CH 615193A5
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- alkyl
- carbon atoms
- compounds
- iii
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 23
- 238000002360 preparation method Methods 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- -1 phosphonic acid diester halides Chemical class 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 241000238631 Hexapoda Species 0.000 claims description 6
- 241000238876 Acari Species 0.000 claims description 5
- 230000000895 acaricidal effect Effects 0.000 claims description 5
- 230000000749 insecticidal effect Effects 0.000 claims description 5
- QEASJVYPHMYPJM-UHFFFAOYSA-N 1,2-dihydrotriazol-5-one Chemical class OC1=CNN=N1 QEASJVYPHMYPJM-UHFFFAOYSA-N 0.000 claims description 4
- 239000000370 acceptor Substances 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 4
- 241000607479 Yersinia pestis Species 0.000 claims description 3
- 150000003008 phosphonic acid esters Chemical class 0.000 claims description 3
- 150000003863 ammonium salts Chemical class 0.000 claims description 2
- 241000251730 Chondrichthyes Species 0.000 claims 3
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 1
- 150000001342 alkaline earth metals Chemical class 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- JIAYYCZEOKXILY-UHFFFAOYSA-N dihydroxy-sulfanylidene-(2h-triazol-4-yloxy)-$l^{5}-phosphane Chemical class OP(O)(=S)OC=1C=NNN=1 JIAYYCZEOKXILY-UHFFFAOYSA-N 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 description 22
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 17
- 239000002904 solvent Substances 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 239000013543 active substance Substances 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 239000003995 emulsifying agent Substances 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 240000007124 Brassica oleracea Species 0.000 description 8
- 229920000151 polyglycol Polymers 0.000 description 7
- 239000010695 polyglycol Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 241000255925 Diptera Species 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical group CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
- 244000046052 Phaseolus vulgaris Species 0.000 description 5
- 125000002877 alkyl aryl group Chemical group 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 241001124076 Aphididae Species 0.000 description 4
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 4
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 4
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 4
- 241000254173 Coleoptera Species 0.000 description 4
- 241000257166 Lucilia cuprina Species 0.000 description 4
- 241001454295 Tetranychidae Species 0.000 description 4
- 241001454293 Tetranychus urticae Species 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 235000013312 flour Nutrition 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 241000239290 Araneae Species 0.000 description 3
- 241001674044 Blattodea Species 0.000 description 3
- 235000011303 Brassica alboglabra Nutrition 0.000 description 3
- 235000011302 Brassica oleracea Nutrition 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000721623 Myzus Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 230000003071 parasitic effect Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- LSQFURWIGPSFHJ-UHFFFAOYSA-N 3-methylpyrazole Chemical compound CC1=CC=N[N]1 LSQFURWIGPSFHJ-UHFFFAOYSA-N 0.000 description 2
- 240000003291 Armoracia rusticana Species 0.000 description 2
- 235000011330 Armoracia rusticana Nutrition 0.000 description 2
- 241000238662 Blatta orientalis Species 0.000 description 2
- 101150003532 CSH gene Proteins 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241001465977 Coccoidea Species 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 239000004606 Fillers/Extenders Substances 0.000 description 2
- 241000257303 Hymenoptera Species 0.000 description 2
- 241000256602 Isoptera Species 0.000 description 2
- 241000254099 Melolontha melolontha Species 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- 241000721621 Myzus persicae Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 241001608568 Phaedon Species 0.000 description 2
- 241001608567 Phaedon cochleariae Species 0.000 description 2
- 241000255969 Pieris brassicae Species 0.000 description 2
- 241000500437 Plutella xylostella Species 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 241001510241 Rhyparobia Species 0.000 description 2
- 244000281247 Ribes rubrum Species 0.000 description 2
- 235000002355 Ribes spicatum Nutrition 0.000 description 2
- 241000254179 Sitophilus granarius Species 0.000 description 2
- 241000254154 Sitophilus zeamais Species 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 244000061456 Solanum tuberosum Species 0.000 description 2
- 235000002595 Solanum tuberosum Nutrition 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 244000078703 ectoparasite Species 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 2
- 229940067157 phenylhydrazine Drugs 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 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
- 150000003852 triazoles Chemical class 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- UUZJJNBYJDFQHL-UHFFFAOYSA-N 1,2,3-triazolidine Chemical compound C1CNNN1 UUZJJNBYJDFQHL-UHFFFAOYSA-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
- AFBBKYQYNPNMAT-UHFFFAOYSA-N 1h-1,2,4-triazol-1-ium-3-thiolate Chemical compound SC=1N=CNN=1 AFBBKYQYNPNMAT-UHFFFAOYSA-N 0.000 description 1
- WWEXEWAAGZKQPB-UHFFFAOYSA-N 4-[(1-hydroxy-3-phenyl-2H-triazol-4-yl)sulfanyl]butanenitrile Chemical compound C(#N)CCCSC1=CN(NN1C1=CC=CC=C1)O WWEXEWAAGZKQPB-UHFFFAOYSA-N 0.000 description 1
- 241001143308 Acanthoscelides Species 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 241000238818 Acheta domesticus Species 0.000 description 1
- 241000256118 Aedes aegypti Species 0.000 description 1
- 241001136265 Agriotes Species 0.000 description 1
- 241000600972 Agriotes fuscicollis Species 0.000 description 1
- 241000218475 Agrotis segetum Species 0.000 description 1
- 244000144730 Amygdalus persica Species 0.000 description 1
- 241001414900 Anopheles stephensi Species 0.000 description 1
- 241001425390 Aphis fabae Species 0.000 description 1
- 241000387321 Aspidiotus nerii Species 0.000 description 1
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- 241000238805 Blaberus Species 0.000 description 1
- 241000238788 Blaberus craniifer Species 0.000 description 1
- 241000238657 Blattella germanica Species 0.000 description 1
- 240000002791 Brassica napus Species 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- 241001444260 Brassicogethes aeneus Species 0.000 description 1
- 241000907225 Bruchidius Species 0.000 description 1
- 241001664277 Byturus Species 0.000 description 1
- 241000257163 Calliphora vicina Species 0.000 description 1
- 241001249699 Capitata Species 0.000 description 1
- 241001107116 Castanospermum australe Species 0.000 description 1
- 241000255580 Ceratitis <genus> Species 0.000 description 1
- RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 1
- IVHVNMLJNASKHW-UHFFFAOYSA-M Chlorphonium chloride Chemical compound [Cl-].CCCC[P+](CCCC)(CCCC)CC1=CC=C(Cl)C=C1Cl IVHVNMLJNASKHW-UHFFFAOYSA-M 0.000 description 1
- 241001124134 Chrysomelidae Species 0.000 description 1
- 241000254137 Cicadidae Species 0.000 description 1
- 241001327638 Cimex lectularius Species 0.000 description 1
- 241001479447 Coccus hesperidum Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 241001094913 Cryptomyzus Species 0.000 description 1
- 241000256059 Culex pipiens Species 0.000 description 1
- 241000328422 Culiseta annulata Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241001641895 Dermestes Species 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 241000353790 Doru Species 0.000 description 1
- 241000255601 Drosophila melanogaster Species 0.000 description 1
- 241001581006 Dysaphis plantaginea Species 0.000 description 1
- 241001425477 Dysdercus Species 0.000 description 1
- 241000630736 Ephestia Species 0.000 description 1
- 241001558857 Eriophyes Species 0.000 description 1
- 241001221110 Eriophyidae Species 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 241000483001 Euproctis chrysorrhoea Species 0.000 description 1
- 241000416536 Euproctis pseudoconspersa Species 0.000 description 1
- 241000239245 Euscelis Species 0.000 description 1
- 241000371383 Fannia Species 0.000 description 1
- 241000255896 Galleria mellonella Species 0.000 description 1
- 241001675057 Gastrophysa viridula Species 0.000 description 1
- 241000258937 Hemiptera Species 0.000 description 1
- 241000652697 Henschoutedenia flexivitta Species 0.000 description 1
- 241001659688 Hercinothrips femoralis Species 0.000 description 1
- 241001251909 Hyalopterus pruni Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241001631692 Lasiocampa quercus Species 0.000 description 1
- 241000948337 Lasius niger Species 0.000 description 1
- 241000255777 Lepidoptera Species 0.000 description 1
- 241000258916 Leptinotarsa decemlineata Species 0.000 description 1
- 241000920471 Lucilia caesar Species 0.000 description 1
- 241000721703 Lymantria dispar Species 0.000 description 1
- 241000721715 Macrosiphum Species 0.000 description 1
- 241000721714 Macrosiphum euphorbiae Species 0.000 description 1
- 241000255685 Malacosoma neustria Species 0.000 description 1
- 241000555303 Mamestra brassicae Species 0.000 description 1
- 241000257159 Musca domestica Species 0.000 description 1
- 241000332345 Myzus cerasi 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
- 241000359016 Nephotettix Species 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- 241000238814 Orthoptera Species 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 241000131101 Oryzaephilus surinamensis Species 0.000 description 1
- 241000488585 Panonychus Species 0.000 description 1
- 241000238661 Periplaneta Species 0.000 description 1
- 241000257186 Phormia regina Species 0.000 description 1
- 241001674048 Phthiraptera Species 0.000 description 1
- 241001396980 Phytonemus pallidus Species 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- 241000690748 Piesma Species 0.000 description 1
- 241000500439 Plutella Species 0.000 description 1
- 241000952063 Polyphagotarsonemus latus Species 0.000 description 1
- 235000005805 Prunus cerasus Nutrition 0.000 description 1
- 235000006040 Prunus persica var persica Nutrition 0.000 description 1
- 235000014441 Prunus serotina Nutrition 0.000 description 1
- 241000722238 Pseudococcus maritimus Species 0.000 description 1
- 241001509967 Reticulitermes flavipes Species 0.000 description 1
- 241000722249 Rhodnius prolixus Species 0.000 description 1
- 241000125167 Rhopalosiphum padi Species 0.000 description 1
- 235000001537 Ribes X gardonianum Nutrition 0.000 description 1
- 235000001535 Ribes X utile Nutrition 0.000 description 1
- 235000016919 Ribes petraeum Nutrition 0.000 description 1
- 235000016911 Ribes sativum Nutrition 0.000 description 1
- 235000016897 Ribes triste Nutrition 0.000 description 1
- 241001412173 Rubus canescens Species 0.000 description 1
- 235000011034 Rubus glaucus Nutrition 0.000 description 1
- 244000235659 Rubus idaeus Species 0.000 description 1
- 235000009122 Rubus idaeus Nutrition 0.000 description 1
- 241000256251 Spodoptera frugiperda Species 0.000 description 1
- 241000256250 Spodoptera littoralis Species 0.000 description 1
- 241000985245 Spodoptera litura Species 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 241000254109 Tenebrio molitor Species 0.000 description 1
- 241001454294 Tetranychus Species 0.000 description 1
- 241001065719 Tetranychus ludeni Species 0.000 description 1
- 241001414989 Thysanoptera Species 0.000 description 1
- 241001238451 Tortrix viridana Species 0.000 description 1
- 241000254113 Tribolium castaneum Species 0.000 description 1
- 241000267823 Trogoderma Species 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical group ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 208000003152 Yellow Fever Diseases 0.000 description 1
- 241001466337 Yponomeuta Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 244000000054 animal parasite Species 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 235000015241 bacon Nutrition 0.000 description 1
- 235000021279 black bean Nutrition 0.000 description 1
- 235000008429 bread Nutrition 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 244000309466 calf Species 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000007957 coemulsifier Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 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
- 239000006260 foam Substances 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 238000003958 fumigation Methods 0.000 description 1
- 238000002309 gasification Methods 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 235000013847 iso-butane Nutrition 0.000 description 1
- 230000001418 larval effect Effects 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 235000020044 madeira Nutrition 0.000 description 1
- 238000004890 malting Methods 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N methyl iso-propyl ketone Natural products CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 239000003531 protein hydrolysate Substances 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
- 230000035484 reaction time Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- 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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having alternatively specified atoms bound to the phosphorus atom and not covered by a single one of groups A01N57/10, A01N57/18, A01N57/26, A01N57/34
- A01N57/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having alternatively specified atoms bound to the phosphorus atom and not covered by a single one of groups A01N57/10, A01N57/18, A01N57/26, A01N57/34 containing heterocyclic 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
- C07F9/6515—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
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Molecular Biology (AREA)
- Agronomy & Crop Science (AREA)
- Biochemistry (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2403711A DE2403711C2 (de) | 1974-01-26 | 1974-01-26 | O-Triazolylthionophosphor(phosphon)-säureester, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide und Akarizide |
Publications (1)
Publication Number | Publication Date |
---|---|
CH615193A5 true CH615193A5 (it) | 1980-01-15 |
Family
ID=5905741
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH84275A CH615193A5 (it) | 1974-01-26 | 1975-01-24 |
Country Status (35)
Country | Link |
---|---|
US (1) | US3981994A (it) |
JP (2) | JPS5810363B2 (it) |
AR (1) | AR206004A1 (it) |
AT (1) | AT329077B (it) |
BE (1) | BE824737A (it) |
BG (1) | BG26202A3 (it) |
BR (1) | BR7500500A (it) |
CA (1) | CA1059521A (it) |
CH (1) | CH615193A5 (it) |
CS (1) | CS177891B2 (it) |
DD (1) | DD118795A5 (it) |
DE (1) | DE2403711C2 (it) |
DK (1) | DK135774C (it) |
EG (1) | EG11538A (it) |
ES (1) | ES434094A1 (it) |
FI (1) | FI750187A (it) |
FR (1) | FR2259106B1 (it) |
GB (1) | GB1452455A (it) |
HU (1) | HU170937B (it) |
IE (1) | IE40483B1 (it) |
IL (1) | IL46498A (it) |
IT (1) | IT1049351B (it) |
KE (1) | KE2720A (it) |
LU (1) | LU71719A1 (it) |
MY (1) | MY7700235A (it) |
NL (1) | NL7500865A (it) |
NO (1) | NO750070L (it) |
OA (1) | OA04886A (it) |
PH (1) | PH11871A (it) |
PL (1) | PL93294B1 (it) |
RO (1) | RO73526A (it) |
SE (1) | SE400973B (it) |
SU (1) | SU577937A3 (it) |
TR (1) | TR18027A (it) |
ZA (1) | ZA75514B (it) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2301400C2 (de) * | 1973-01-12 | 1984-12-13 | Bayer Ag, 5090 Leverkusen | 0-Triazolyl-thionophosphor(phosphon)-säureester und -esteramide, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide und Akarizide |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE637016A (it) * | 1951-04-20 | 1900-01-01 | ||
BE792449A (fr) * | 1971-12-10 | 1973-06-08 | Ciba Geigy | Esters triazolyliques d'acides oxygenes du phosphore et produits pesticides qui en renferment |
BE792450A (fr) * | 1971-12-10 | 1973-06-08 | Ciba Geigy | Composes organophosphores et produits pesticides qui en contiennent |
-
1974
- 1974-01-24 ZA ZA00750514A patent/ZA75514B/xx unknown
- 1974-01-26 DE DE2403711A patent/DE2403711C2/de not_active Expired
-
1975
- 1975-01-01 AR AR257388A patent/AR206004A1/es active
- 1975-01-07 PH PH16682A patent/PH11871A/en unknown
- 1975-01-08 RO RO7581070A patent/RO73526A/ro unknown
- 1975-01-09 US US05/539,898 patent/US3981994A/en not_active Expired - Lifetime
- 1975-01-10 NO NO750070A patent/NO750070L/no unknown
- 1975-01-21 BG BG7528760A patent/BG26202A3/xx unknown
- 1975-01-23 DK DK20875A patent/DK135774C/da active
- 1975-01-23 IL IL46498A patent/IL46498A/en unknown
- 1975-01-24 IT IT19581/75A patent/IT1049351B/it active
- 1975-01-24 JP JP50009914A patent/JPS5810363B2/ja not_active Expired
- 1975-01-24 ES ES434094A patent/ES434094A1/es not_active Expired
- 1975-01-24 SE SE7500776A patent/SE400973B/xx unknown
- 1975-01-24 FI FI750187A patent/FI750187A/fi not_active Application Discontinuation
- 1975-01-24 SU SU7502102030A patent/SU577937A3/ru active
- 1975-01-24 LU LU71719*A patent/LU71719A1/xx unknown
- 1975-01-24 JP JP991375A patent/JPS5735837B2/ja not_active Expired
- 1975-01-24 FR FR7502301A patent/FR2259106B1/fr not_active Expired
- 1975-01-24 OA OA55391A patent/OA04886A/xx unknown
- 1975-01-24 AT AT53075*#A patent/AT329077B/de active
- 1975-01-24 TR TR18027A patent/TR18027A/xx unknown
- 1975-01-24 BR BR500/75A patent/BR7500500A/pt unknown
- 1975-01-24 IE IE138/75A patent/IE40483B1/xx unknown
- 1975-01-24 NL NL7500865A patent/NL7500865A/xx not_active Application Discontinuation
- 1975-01-24 DD DD183808A patent/DD118795A5/xx unknown
- 1975-01-24 GB GB318475A patent/GB1452455A/en not_active Expired
- 1975-01-24 HU HU75BA00003193A patent/HU170937B/hu unknown
- 1975-01-24 CA CA218,598A patent/CA1059521A/en not_active Expired
- 1975-01-24 CH CH84275A patent/CH615193A5/de not_active IP Right Cessation
- 1975-01-24 PL PL1975177527A patent/PL93294B1/pl unknown
- 1975-01-24 BE BE152670A patent/BE824737A/xx unknown
- 1975-01-25 EG EG29A patent/EG11538A/xx active
- 1975-01-27 CS CS526A patent/CS177891B2/cs unknown
-
1977
- 1977-04-05 KE KE2720A patent/KE2720A/xx unknown
- 1977-12-30 MY MY235/77A patent/MY7700235A/xx unknown
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
DE2216551A1 (de) | 0-(n-alkoxy-benzimidoyl)-(thiono)phosphor (hosphon)-saeureester, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide | |
DE2440677A1 (de) | Pyrimidinylthionophosphonsaeureester, verfahren zu ihrer herstellung und ihre verwendung als insektizide, akarizide und nematizide | |
DE2220629C3 (de) | Benzisoxazolo(thiono)phosphor(phosphon)säureester, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Insektizide und Akarizide | |
DE2304062C2 (de) | 0-Aryl-thionoalkanphosphonsäureesterimidderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide, Akarizide und Nematizide | |
DE2340080A1 (de) | 0-phenyl-thionophosphor(phosphon)-saeureesteramid- bzw. -imidderivate, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide | |
DE2537047A1 (de) | Vinylthionophosphorsaeureester, verfahren zu ihrer herstellung sowie ihre verwendung als insektizide und akarizide | |
DE2422548C2 (de) | 0-Triazolyl-(thiono)-phosphor(phosphon)-säureester und -esteramide, Verfahren zu ihrer Herstellung sowieihre Verwendung als Insektizide, Akarizide und Nematizide | |
DE2350631C2 (de) | Triazolothiazol-(thiono)-phosphor(phosphon)-säureester, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Insektizide und Akarizide | |
DE2431849A1 (de) | N-dithiophosphoryl-carbaminsaeureester, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide | |
DE2211338A1 (de) | N-(aminomethyliden)-thiol-phosphorsaeureesterimide, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide | |
DE2360548C3 (de) | 2-Cyanophenyldithiophosphorsäureester, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide und Akarizide | |
DE2403711C2 (de) | O-Triazolylthionophosphor(phosphon)-säureester, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide und Akarizide | |
DE2216552B2 (de) | Disubstituierte N- [Aminomethyliden] - thiol-(thiono)-phosphorsäureesterimide, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide und Akarizide | |
DE2049692A1 (de) | Pyrazolo-(thiono)-phosphor(phosphon)säureester, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Insektizide und Akarizide | |
DE2019597C3 (de) | O-Phenyl-thiono-äthanphosphonsäureesteramide, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Insektizide, Akarizide und Nematizide | |
DE2424571A1 (de) | S-triazolopyridinmethyl-thiolo(thion)phosphor(phosphon)-saeureester bzw. -esteramide, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide | |
DE2240032A1 (de) | S-(amidocarbonyl)-methyl-monothiophosphorsaeureesteramide, verfahren zu ihrer herstellung sowie ihre verwendung als insektizide und akarizide | |
DE2515794A1 (de) | S-triazolobenzopyrazinmethyl(thiono) thiolphosphor(phosphon)saeureester, verfahren zu ihrer herstellung und ihre verwendung als insektizide | |
DE2064307A1 (de) | Thiazolo-(thiono)-phosphor-(phosphon)säureester, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Insektizide | |
DE2010889A1 (de) | S-Alkylmercaptomethyl-thio- bzw.-dithiophosphor(phosphon)-säureester, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Insektizide und Akarizide | |
DE2415058A1 (de) | Pyrimidin(2)yl-thionophosphorsaeureester, verfahren zu ihrer herstellung sowie ihre verwendung als insektizide, akarizide und nematizide | |
DE2420069A1 (de) | N,n-dimethyl-n'- eckige klammer auf 0-phenyl(thiono)-alkanphosphonyl eckige klammer zu formamidine, verfahren zu ihrer herstellung und ihre verwendung als insektizide, akarizide und nematizide | |
DE2532628A1 (de) | Fluorsubstituierte carbaminylmethyldithioalkanphosphonsaeureester, verfahren zu ihrer herstellung sowie ihre verwendung als insektizide, akarizide und nematizide | |
DE2528692A1 (de) | Pyridazinyl(thiono)phosphorsaeureester, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide | |
DE2438789A1 (de) | 2- eckige klammer auf (thiono)phosphoryl(phosphonyl) eckige klammer zu -3oxotriazolopyridine, verfahren zu ihrer herstellung sowie ihre verwendung als insektizide und akarizide |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PL | Patent ceased |