IL35096A - Thiol-and thionothiol-phosphoric acid esters,their preparation and their use as insecticides and acaricides - Google Patents
Thiol-and thionothiol-phosphoric acid esters,their preparation and their use as insecticides and acaricidesInfo
- Publication number
- IL35096A IL35096A IL35096A IL3509670A IL35096A IL 35096 A IL35096 A IL 35096A IL 35096 A IL35096 A IL 35096A IL 3509670 A IL3509670 A IL 3509670A IL 35096 A IL35096 A IL 35096A
- Authority
- IL
- Israel
- Prior art keywords
- preparation
- thiol
- thionothiol
- acid esters
- insecticides
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title description 12
- 230000000895 acaricidal effect Effects 0.000 title description 4
- 239000002917 insecticide Substances 0.000 title description 3
- 239000000642 acaricide Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 43
- 239000002253 acid Substances 0.000 claims description 12
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 239000005864 Sulphur Substances 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 22
- 239000000203 mixture Substances 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- 239000002904 solvent Substances 0.000 description 11
- -1 methoxy, ethoxy Chemical group 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 241000255925 Diptera Species 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 241000238876 Acari Species 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 239000003085 diluting agent Substances 0.000 description 7
- 239000003995 emulsifying agent Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 241000238631 Hexapoda Species 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 230000006378 damage Effects 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 241000254173 Coleoptera Species 0.000 description 5
- 241000500437 Plutella xylostella Species 0.000 description 5
- 241001454295 Tetranychidae Species 0.000 description 5
- 241001454293 Tetranychus urticae Species 0.000 description 5
- 241000607479 Yersinia pestis Species 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 150000003568 thioethers Chemical class 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- HFLJXEKMXYJYAJ-UHFFFAOYSA-N 3-bromo-3-(2-bromo-4-chlorobutan-2-yl)sulfanyl-1-chlorobutane Chemical compound ClCCC(C)(Br)SC(CCCl)(C)Br HFLJXEKMXYJYAJ-UHFFFAOYSA-N 0.000 description 3
- 241001510109 Blaberus giganteus Species 0.000 description 3
- 241000255580 Ceratitis <genus> Species 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 241000257159 Musca domestica Species 0.000 description 3
- 241000721621 Myzus persicae Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 241000488583 Panonychus ulmi Species 0.000 description 3
- 244000046052 Phaseolus vulgaris Species 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- 241000254179 Sitophilus granarius Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- QABPJZSQKBJZSK-UHFFFAOYSA-N 2-bromopropane-2-thiol Chemical compound BrC(C)(C)S QABPJZSQKBJZSK-UHFFFAOYSA-N 0.000 description 2
- MBNVSWHUJDDZRH-UHFFFAOYSA-N 2-methylthiirane Chemical compound CC1CS1 MBNVSWHUJDDZRH-UHFFFAOYSA-N 0.000 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- 241001143309 Acanthoscelides obtectus Species 0.000 description 2
- 241000238818 Acheta domesticus Species 0.000 description 2
- 241000256118 Aedes aegypti Species 0.000 description 2
- 241001124076 Aphididae Species 0.000 description 2
- 241001425390 Aphis fabae Species 0.000 description 2
- 241000387321 Aspidiotus nerii Species 0.000 description 2
- 241000238662 Blatta orientalis Species 0.000 description 2
- 241000238657 Blattella germanica Species 0.000 description 2
- 240000007124 Brassica oleracea Species 0.000 description 2
- 241001444260 Brassicogethes aeneus Species 0.000 description 2
- 241001664260 Byturus tomentosus Species 0.000 description 2
- 241000255579 Ceratitis capitata Species 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 241000256059 Culex pipiens Species 0.000 description 2
- 241000255601 Drosophila melanogaster Species 0.000 description 2
- 241001581006 Dysaphis plantaginea 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
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241000258916 Leptinotarsa decemlineata Species 0.000 description 2
- 241000255685 Malacosoma neustria 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
- 241000238675 Periplaneta americana Species 0.000 description 2
- 241001608567 Phaedon cochleariae Species 0.000 description 2
- 241001396980 Phytonemus pallidus Species 0.000 description 2
- 241000500439 Plutella Species 0.000 description 2
- 241000952063 Polyphagotarsonemus latus Species 0.000 description 2
- 241000722238 Pseudococcus maritimus Species 0.000 description 2
- 241001509967 Reticulitermes flavipes Species 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
- 241000254154 Sitophilus zeamais Species 0.000 description 2
- 241000256251 Spodoptera frugiperda Species 0.000 description 2
- 241001177161 Stegobium paniceum Species 0.000 description 2
- 241000254109 Tenebrio molitor Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 241001414989 Thysanoptera Species 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000010410 dusting Methods 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 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 2
- 239000011521 glass Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- 229920000151 polyglycol Polymers 0.000 description 2
- 239000010695 polyglycol Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- APQIUTYORBAGEZ-UHFFFAOYSA-N 1,1-dibromoethane Chemical compound CC(Br)Br APQIUTYORBAGEZ-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-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
- 241000253994 Acyrthosiphon pisum Species 0.000 description 1
- 241000426834 Aegina Species 0.000 description 1
- 241001136265 Agriotes Species 0.000 description 1
- 241001136249 Agriotes lineatus Species 0.000 description 1
- 241000218475 Agrotis segetum Species 0.000 description 1
- 241000449794 Alabama argillacea Species 0.000 description 1
- 241001414900 Anopheles stephensi Species 0.000 description 1
- 241000238788 Blaberus craniifer Species 0.000 description 1
- 241001674044 Blattodea Species 0.000 description 1
- 235000011303 Brassica alboglabra Nutrition 0.000 description 1
- 235000011302 Brassica oleracea Nutrition 0.000 description 1
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 1
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 1
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 241000907225 Bruchidius Species 0.000 description 1
- 241000257163 Calliphora vicina Species 0.000 description 1
- 235000005940 Centaurea cyanus Nutrition 0.000 description 1
- 240000004385 Centaurea cyanus Species 0.000 description 1
- 241000254137 Cicadidae Species 0.000 description 1
- 241001327638 Cimex lectularius Species 0.000 description 1
- 241001415288 Coccidae Species 0.000 description 1
- 241001465977 Coccoidea 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
- 241000289763 Dasygaster padockina Species 0.000 description 1
- 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
- 241001425477 Dysdercus Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000122098 Ephestia kuehniella Species 0.000 description 1
- 241000483001 Euproctis chrysorrhoea Species 0.000 description 1
- 241000953886 Fannia canicularis 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
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-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
- 241000256602 Isoptera Species 0.000 description 1
- 241000948337 Lasius niger 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
- 241000555303 Mamestra brassicae Species 0.000 description 1
- 241000254071 Melolontha Species 0.000 description 1
- 241000254099 Melolontha melolontha Species 0.000 description 1
- 241001465754 Metazoa 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
- 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
- 241001491877 Operophtera brumata Species 0.000 description 1
- 241000238887 Ornithodoros Species 0.000 description 1
- 241001481099 Ornithodoros turicata Species 0.000 description 1
- 241000238814 Orthoptera Species 0.000 description 1
- 241000131101 Oryzaephilus surinamensis Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 241001548358 Parapiesma quadratum Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 241000257149 Phormia Species 0.000 description 1
- 241000257186 Phormia regina Species 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- 241000255969 Pieris brassicae Species 0.000 description 1
- 241000690748 Piesma Species 0.000 description 1
- 235000005805 Prunus cerasus Nutrition 0.000 description 1
- 241001097374 Pselliopus cinctus Species 0.000 description 1
- 241001510236 Rhyparobia maderae Species 0.000 description 1
- 241000985245 Spodoptera litura Species 0.000 description 1
- 241000255588 Tephritidae Species 0.000 description 1
- 241001414831 Triatoma infestans Species 0.000 description 1
- 241000267823 Trogoderma Species 0.000 description 1
- 241000267822 Trogoderma granarium Species 0.000 description 1
- 241001466337 Yponomeuta Species 0.000 description 1
- 241000064240 Yponomeuta padellus 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
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 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
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 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
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 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
- 238000001816 cooling Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 238000003958 fumigation Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229960004592 isopropanol Drugs 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 201000004792 malaria Diseases 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 230000001473 noxious effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant 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
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/1651—Esters of thiophosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
-
- 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
- A01N57/04—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 acyclic or cycloaliphatic 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4075—Esters with hydroxyalkyl compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Dentistry (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691945700 DE1945700A1 (de) | 1969-09-10 | 1969-09-10 | Thiol- bzw. Thionothiolphosphor- oder phosphonsaeureester,Verfahren zu ihrer Herstellung sowie ihre Verwendung als Insektizide und Akarizide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL35096A0 IL35096A0 (en) | 1970-10-30 |
| IL35096A true IL35096A (en) | 1973-04-30 |
Family
ID=5745033
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL35096A IL35096A (en) | 1969-09-10 | 1970-08-11 | Thiol-and thionothiol-phosphoric acid esters,their preparation and their use as insecticides and acaricides |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3784653A (fr) |
| BE (1) | BE755977A (fr) |
| CH (1) | CH507305A (fr) |
| DE (1) | DE1945700A1 (fr) |
| ES (1) | ES383483A1 (fr) |
| FR (1) | FR2061262A5 (fr) |
| GB (1) | GB1268600A (fr) |
| IL (1) | IL35096A (fr) |
| NL (1) | NL7013413A (fr) |
-
0
- BE BE755977D patent/BE755977A/fr unknown
-
1969
- 1969-09-10 DE DE19691945700 patent/DE1945700A1/de active Pending
-
1970
- 1970-08-11 IL IL35096A patent/IL35096A/en unknown
- 1970-08-14 CH CH1222570A patent/CH507305A/de not_active IP Right Cessation
- 1970-08-19 US US00065323A patent/US3784653A/en not_active Expired - Lifetime
- 1970-09-09 ES ES383483A patent/ES383483A1/es not_active Expired
- 1970-09-10 FR FR7032934A patent/FR2061262A5/fr not_active Expired
- 1970-09-10 NL NL7013413A patent/NL7013413A/xx unknown
- 1970-09-10 GB GB43367/70A patent/GB1268600A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH507305A (de) | 1971-05-15 |
| FR2061262A5 (fr) | 1971-06-18 |
| US3784653A (en) | 1974-01-08 |
| NL7013413A (fr) | 1971-03-12 |
| DE1945700A1 (de) | 1971-03-18 |
| ES383483A1 (es) | 1973-03-01 |
| GB1268600A (en) | 1972-03-29 |
| IL35096A0 (en) | 1970-10-30 |
| BE755977A (fr) | 1971-03-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| IL46172A (en) | Pyrimidine-thionothiolphosphoric acid esters their preparation and their use as insecticides and acaricides | |
| IL44235A (en) | N-sulphenylated n-methylcarbamidoximes of 2-oxoalkanenitriles their preparation and insecticidal acaricidal and fungicidal compositions containing them | |
| IL34985A (en) | Triazolothiazole esters of phosphoric, phosphonic and phosphonic acids and of the appropriate tionic acids, their preparation and use as insecticides and acaricides | |
| IL29504A (en) | 3,5,6-trichloropyridyl-2-thionophosphonic acid esters | |
| IL34950A (en) | Esters of thiazolo-phosphoric and -phosphonic,thiazolo-thionophosphoric and -thionophosphonic acid,their preparation and use as insecticides and acaricides | |
| US3547920A (en) | Phosphoric,phosphonic,thionophosphoric and thionophosphonic acid esters | |
| IL31640A (en) | Thionophosphonic acid esters,their preparation and use for pest control | |
| US3763285A (en) | 1-phenyl-2-cyanovinyl(thio)-phosphoric or-phosphonic acid esters | |
| IL46198A (en) | Triazolothiazolyl-(thiono)-phosphoric (phosphonic)- acid esters their preparation and insecticidal and acaricidal compositions containing them | |
| US3974171A (en) | O-[3-methyl-1,3,4-triazole-(2,3,-b)-thiazol(6)yl]-(thiono)-phosphoric(phosphonic) acid esters | |
| IL37223A (en) | Esters of O-pyrazolo-pyrimidine- (thionic) - phosphorous and phosphonic acids, their preparation and use as insecticides and mites | |
| US3966920A (en) | O,S-Dialkyl-O-(2-cyanophenyl)-thionothiolphosphoric acid esters and insecticidal and acaricidal compositions and method | |
| US3743687A (en) | Lower alkyl-s-(1-bromopropyl-(2)-mercaptomethyl)-(thiono)thiolphosphoric or phosphonic acid esters | |
| IL34101A (en) | O-alkyl-s-(n,n-dialkylaminocarbamyl)-methyl-n-monoalkylamido-thiolphosphoric and thionothiolphosphoric acid esters,their preparation and use as insecticides and acaricides | |
| IL32650A (en) | Thionophosphonic acid esters,their preparation and use for combatting insects | |
| US3752871A (en) | O - alkyl - n-monoalkyl-s-(n'-acyl-carbamylmethyl) - thionothiolphosphoric acid ester amides | |
| IL38701A (en) | Substituted pyrazol(3)yl-carbamic acid esters,their preparation and their use as insecticides or acaricides | |
| US3733378A (en) | Amido-o-lower alkyl-s-allylmercapto-methylthiolphosphoric acid esters | |
| US3862271A (en) | O-alkyl-(thiono) thiol-s-(s-alkylmercapto-s-benzylmercapto-methyl)-phosphoric (phosphonic) acid esters | |
| IL33731A (en) | O,o-dialkyl-s-(1,2,2-trichloroethyl)-thionothiolphosphoric acid esters and o-alkyl-s-(1,2,2-trichloroethyl)-alkane-thionothiolphosphonic acid esters,their preparation and use as insecticides | |
| US3712937A (en) | S-(1,3-dihalo-prop-2-yl-mercaptomethyl)-thiol and thionothiol phosphoric and phosphonic acid esters | |
| US3536789A (en) | Phospho-alpha-oximino-cyanophenyl acetic acid nitriles | |
| IL35096A (en) | Thiol-and thionothiol-phosphoric acid esters,their preparation and their use as insecticides and acaricides | |
| IL41500A (en) | O-alkyl-s-carbamoyloxymethyl-thiolphosphoric,thionothiolphosphoric,thiolphosphoric and thionothiolphosphonic acid esters,their production and their use as insecticides | |
| US3652740A (en) | O-alkyl-o-phenyl-thiolphosphoric acid esters |