DE2241625A1 - Halogenalkylthionophosphorsaeureester, verfahren zu ihrer herstellung und ihre verwendung als insektizide und nematizide - Google Patents
Halogenalkylthionophosphorsaeureester, verfahren zu ihrer herstellung und ihre verwendung als insektizide und nematizideInfo
- Publication number
- DE2241625A1 DE2241625A1 DE2241625A DE2241625A DE2241625A1 DE 2241625 A1 DE2241625 A1 DE 2241625A1 DE 2241625 A DE2241625 A DE 2241625A DE 2241625 A DE2241625 A DE 2241625A DE 2241625 A1 DE2241625 A1 DE 2241625A1
- Authority
- DE
- Germany
- Prior art keywords
- active ingredient
- acid esters
- compounds according
- acid ester
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 16
- 150000002148 esters Chemical class 0.000 title claims description 15
- 239000002253 acid Substances 0.000 title claims description 14
- 230000008569 process Effects 0.000 title claims description 13
- 239000002917 insecticide Substances 0.000 title claims description 3
- 239000005645 nematicide Substances 0.000 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title description 2
- -1 Dichlorovinylthionophosphoric acid ester Chemical class 0.000 claims description 14
- 241000238631 Hexapoda Species 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 11
- 230000000749 insecticidal effect Effects 0.000 claims description 8
- 150000001298 alcohols Chemical class 0.000 claims description 6
- 241000607479 Yersinia pestis Species 0.000 claims description 5
- 239000004606 Fillers/Extenders Substances 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 241000244206 Nematoda Species 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 description 43
- 239000002904 solvent Substances 0.000 description 23
- 239000000243 solution Substances 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 241001465754 Metazoa Species 0.000 description 14
- 241000255925 Diptera Species 0.000 description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
- 229910052794 bromium Inorganic materials 0.000 description 7
- 239000003995 emulsifying agent Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical group CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 230000006378 damage Effects 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 230000001069 nematicidal effect Effects 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000254173 Coleoptera Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 241000254179 Sitophilus granarius Species 0.000 description 3
- 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
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 241000256118 Aedes aegypti Species 0.000 description 2
- 241001124076 Aphididae Species 0.000 description 2
- 241001510109 Blaberus giganteus Species 0.000 description 2
- 241000255580 Ceratitis <genus> 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
- 241001465977 Coccoidea Species 0.000 description 2
- 241001414892 Delia radicum 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
- 241000257303 Hymenoptera Species 0.000 description 2
- 241000256602 Isoptera Species 0.000 description 2
- 241000721703 Lymantria dispar Species 0.000 description 2
- 241000254099 Melolontha melolontha 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
- 241000238814 Orthoptera Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 231100000674 Phytotoxicity Toxicity 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
- 235000011034 Rubus glaucus Nutrition 0.000 description 2
- 244000235659 Rubus idaeus Species 0.000 description 2
- 235000009122 Rubus idaeus Nutrition 0.000 description 2
- 241000254154 Sitophilus zeamais Species 0.000 description 2
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
- 244000061456 Solanum tuberosum Species 0.000 description 2
- 235000002595 Solanum tuberosum Nutrition 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 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
- 239000012141 concentrate Substances 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 235000013312 flour Nutrition 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 2
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical class CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- AWOYKRJEPKDQRB-UHFFFAOYSA-N 2,2-dichloroethenoxy-dihydroxy-sulfanylidene-$l^{5}-phosphane Chemical class OP(O)(=S)OC=C(Cl)Cl AWOYKRJEPKDQRB-UHFFFAOYSA-N 0.000 description 1
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 1
- 241001143309 Acanthoscelides obtectus Species 0.000 description 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 1
- 241000238818 Acheta domesticus Species 0.000 description 1
- 241000426834 Aegina Species 0.000 description 1
- 241001136265 Agriotes Species 0.000 description 1
- 241000218475 Agrotis segetum Species 0.000 description 1
- 241000256186 Anopheles <genus> Species 0.000 description 1
- 241001425390 Aphis fabae Species 0.000 description 1
- 240000003291 Armoracia rusticana Species 0.000 description 1
- 235000011330 Armoracia rusticana Nutrition 0.000 description 1
- 241000387321 Aspidiotus nerii Species 0.000 description 1
- 235000021537 Beetroot Nutrition 0.000 description 1
- 241000238788 Blaberus craniifer Species 0.000 description 1
- 241000238657 Blattella germanica Species 0.000 description 1
- 241001674044 Blattodea Species 0.000 description 1
- 240000007124 Brassica oleracea Species 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
- 241001444260 Brassicogethes aeneus Species 0.000 description 1
- 241000907225 Bruchidius Species 0.000 description 1
- 241001664260 Byturus tomentosus Species 0.000 description 1
- 241000257163 Calliphora vicina Species 0.000 description 1
- 241001107116 Castanospermum australe Species 0.000 description 1
- 241000254137 Cicadidae Species 0.000 description 1
- 241001479447 Coccus hesperidum Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 241000456565 Cryptolestes pusillus Species 0.000 description 1
- 241001094913 Cryptomyzus Species 0.000 description 1
- 241000256059 Culex pipiens Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241000627010 Delia brassica Species 0.000 description 1
- 241001641895 Dermestes 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
- 241000483001 Euproctis chrysorrhoea Species 0.000 description 1
- 241000239245 Euscelis Species 0.000 description 1
- 241000953886 Fannia canicularis Species 0.000 description 1
- 241000255896 Galleria mellonella Species 0.000 description 1
- 241001675057 Gastrophysa viridula Species 0.000 description 1
- 241000219146 Gossypium 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
- 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
- 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
- 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
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 241000131101 Oryzaephilus surinamensis Species 0.000 description 1
- 241000238661 Periplaneta Species 0.000 description 1
- 241001608567 Phaedon cochleariae Species 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 241000257149 Phormia Species 0.000 description 1
- 241000690748 Piesma Species 0.000 description 1
- 108010009736 Protein Hydrolysates Proteins 0.000 description 1
- 235000005805 Prunus cerasus 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
- 241001510241 Rhyparobia Species 0.000 description 1
- 241001510236 Rhyparobia maderae 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
- 244000281247 Ribes rubrum Species 0.000 description 1
- 235000002355 Ribes spicatum Nutrition 0.000 description 1
- 241001412173 Rubus canescens Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 241000256250 Spodoptera littoralis Species 0.000 description 1
- 241000985245 Spodoptera litura Species 0.000 description 1
- 241001177161 Stegobium paniceum Species 0.000 description 1
- 241001494115 Stomoxys calcitrans Species 0.000 description 1
- 241000254109 Tenebrio molitor Species 0.000 description 1
- 241000255588 Tephritidae 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
- 241000267822 Trogoderma granarium Species 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical class ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 208000003152 Yellow Fever Diseases 0.000 description 1
- 241001466337 Yponomeuta Species 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000002969 artificial stone Substances 0.000 description 1
- 125000003118 aryl 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
- 244000309466 calf Species 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000006731 degradation reaction Methods 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
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- ZQXDUKMRLYGEHT-UHFFFAOYSA-N ethene hydrochloride Chemical compound Cl.C=C.C=C ZQXDUKMRLYGEHT-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 235000020044 madeira Nutrition 0.000 description 1
- 201000004792 malaria Diseases 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 229920000609 methyl cellulose Polymers 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
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 230000002035 prolonged effect Effects 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
- 238000000746 purification Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000004575 stone 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
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 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
-
- 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
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
- A01N57/14—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing aromatic 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
- C07F9/06—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
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (30)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2241625A DE2241625A1 (de) | 1972-08-24 | 1972-08-24 | Halogenalkylthionophosphorsaeureester, verfahren zu ihrer herstellung und ihre verwendung als insektizide und nematizide |
| US00388686A US3845174A (en) | 1972-08-24 | 1973-08-15 | O,o-dialkyl-o-(1,2-dibromo-2,2-dichloroethyl)-thionophosphoric acid ester |
| AU59387/73A AU474984B2 (en) | 1972-08-24 | 1973-08-20 | Haloalkylthionophosphoric acid esters, processes and their production and their use as insecticides and nematocides |
| RO7383640A RO66312A (ro) | 1972-08-24 | 1973-08-20 | Procedeu de obtinere a esterilor acizilor halogenalchiltionofosforici |
| RO7300075845A RO64171A (fr) | 1972-08-24 | 1973-08-20 | Procede pour obtenir des esters d'acides halogenealkylthionophosphoriques |
| TR17846A TR17846A (tr) | 1972-08-24 | 1973-08-21 | Haloalkilitionofosforik asid esterleri,imallerine mahsus usul ve insektisid ve nematosidler olarak kullanilmalari |
| IL7343038A IL43038A (en) | 1972-08-24 | 1973-08-21 | Haloalkylthionophosphoric acid esters,their production and their use as insecticides and nematocides |
| NL7311513A NL7311513A (US06826419-20041130-M00005.png) | 1972-08-24 | 1973-08-21 | |
| CH1202373A CH583514A5 (US06826419-20041130-M00005.png) | 1972-08-24 | 1973-08-21 | |
| JP48093396A JPS4956928A (US06826419-20041130-M00005.png) | 1972-08-24 | 1973-08-22 | |
| BE134808A BE803878A (fr) | 1972-08-24 | 1973-08-22 | Nouveaux esters d'acides halogenalkylthionophosphoriques, leur procede de preparation et leur application comme insecticides et nematicides |
| LU68285A LU68285A1 (US06826419-20041130-M00005.png) | 1972-08-24 | 1973-08-22 | |
| JP48093397A JPS4955843A (US06826419-20041130-M00005.png) | 1972-08-24 | 1973-08-22 | |
| SU731957434A SU730272A3 (ru) | 1972-08-24 | 1973-08-22 | Нематоцид |
| PL1973175463A PL90624B1 (US06826419-20041130-M00005.png) | 1972-08-24 | 1973-08-22 | |
| PL1973164790A PL89381B1 (US06826419-20041130-M00005.png) | 1972-08-24 | 1973-08-22 | |
| IE1476/73A IE38127B1 (en) | 1972-08-24 | 1973-08-23 | Haloalkylthionophosphoric acid esters processes for their production and their use as insecticides and nematocides |
| ES418130A ES418130A1 (es) | 1972-08-24 | 1973-08-23 | Procedimiento para preparar esteres de acidos halogenoal- quiltionofosforicos. |
| DK465573A DK133006C (da) | 1972-08-24 | 1973-08-23 | Insecticidt og nematodicidt virksomme halogenalkylthionophosphorsyreestere |
| ZA735792A ZA735792B (en) | 1972-08-24 | 1973-08-23 | Haloalkylthionophosphoric acid esters,processes for their production and their use as insecticides and nematocides |
| BR6508/73A BR7306508D0 (pt) | 1972-08-24 | 1973-08-23 | Processo para a preparacao de esteres halogenalquilicos de acido tionofosforico e composicoes insecticidas e nematocidas a base destes |
| DD173057A DD108993A5 (US06826419-20041130-M00005.png) | 1972-08-24 | 1973-08-23 | |
| HUBA2970A HU166812B (US06826419-20041130-M00005.png) | 1972-08-24 | 1973-08-23 | |
| CA179,538A CA1014569A (en) | 1972-08-24 | 1973-08-23 | Haloalkylthionophosphoric acid esters, processes for their production and their use as insecticides and nematocides |
| AT738373A AT326951B (de) | 1972-08-24 | 1973-08-24 | Insektizides und nematizides mittel |
| CS7300005936A CS183708B2 (en) | 1972-08-24 | 1973-08-24 | Insecticide and nematocide agents and mode of production of active substances |
| GB4021073A GB1380385A (en) | 1972-08-24 | 1973-08-24 | Haloalkylthionophosphoric acid esters processes for their production and their use as insecticides and nematocides |
| FR7330748A FR2197015B1 (US06826419-20041130-M00005.png) | 1972-08-24 | 1973-08-24 | |
| ES443513A ES443513A1 (es) | 1972-08-24 | 1975-12-16 | Procedimiento para preparar esteres de acidos halogenoal- quiltionofosforicos. |
| CS77287A CS188857B2 (en) | 1972-08-24 | 1977-01-17 | Method of preparation of the new halogenalkylesters of the thionophosphor acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2241625A DE2241625A1 (de) | 1972-08-24 | 1972-08-24 | Halogenalkylthionophosphorsaeureester, verfahren zu ihrer herstellung und ihre verwendung als insektizide und nematizide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2241625A1 true DE2241625A1 (de) | 1974-03-14 |
Family
ID=5854414
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2241625A Pending DE2241625A1 (de) | 1972-08-24 | 1972-08-24 | Halogenalkylthionophosphorsaeureester, verfahren zu ihrer herstellung und ihre verwendung als insektizide und nematizide |
Country Status (25)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4866045A (en) * | 1984-04-30 | 1989-09-12 | E. I. Du Pont Nemours And Company | Tetrachloroethyl phosphorothioate soil insecticide |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2140270A1 (en) * | 1971-06-07 | 1973-01-19 | Aries Robert | Organophosphorus insecticides - stabilized by styrenes |
-
1972
- 1972-08-24 DE DE2241625A patent/DE2241625A1/de active Pending
-
1973
- 1973-08-15 US US00388686A patent/US3845174A/en not_active Expired - Lifetime
- 1973-08-20 RO RO7383640A patent/RO66312A/ro unknown
- 1973-08-20 AU AU59387/73A patent/AU474984B2/en not_active Expired
- 1973-08-20 RO RO7300075845A patent/RO64171A/ro unknown
- 1973-08-21 TR TR17846A patent/TR17846A/xx unknown
- 1973-08-21 CH CH1202373A patent/CH583514A5/xx not_active IP Right Cessation
- 1973-08-21 IL IL7343038A patent/IL43038A/en unknown
- 1973-08-21 NL NL7311513A patent/NL7311513A/xx not_active Application Discontinuation
- 1973-08-22 JP JP48093396A patent/JPS4956928A/ja active Pending
- 1973-08-22 SU SU731957434A patent/SU730272A3/ru active
- 1973-08-22 BE BE134808A patent/BE803878A/xx unknown
- 1973-08-22 PL PL1973164790A patent/PL89381B1/pl unknown
- 1973-08-22 JP JP48093397A patent/JPS4955843A/ja active Pending
- 1973-08-22 PL PL1973175463A patent/PL90624B1/pl unknown
- 1973-08-22 LU LU68285A patent/LU68285A1/xx unknown
- 1973-08-23 DK DK465573A patent/DK133006C/da active
- 1973-08-23 DD DD173057A patent/DD108993A5/xx unknown
- 1973-08-23 ZA ZA735792A patent/ZA735792B/xx unknown
- 1973-08-23 ES ES418130A patent/ES418130A1/es not_active Expired
- 1973-08-23 IE IE1476/73A patent/IE38127B1/xx unknown
- 1973-08-23 HU HUBA2970A patent/HU166812B/hu unknown
- 1973-08-23 BR BR6508/73A patent/BR7306508D0/pt unknown
- 1973-08-23 CA CA179,538A patent/CA1014569A/en not_active Expired
- 1973-08-24 FR FR7330748A patent/FR2197015B1/fr not_active Expired
- 1973-08-24 GB GB4021073A patent/GB1380385A/en not_active Expired
- 1973-08-24 AT AT738373A patent/AT326951B/de not_active IP Right Cessation
- 1973-08-24 CS CS7300005936A patent/CS183708B2/cs unknown
-
1975
- 1975-12-16 ES ES443513A patent/ES443513A1/es not_active Expired
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2343931A1 (de) | Pyrimidin(4)-yl-(thiono)-(thiol)-phosphor(phosphon)-saeureester bzw. -esteramide, verfahren zu ihrer herstellung sowie ihre verwendung als insetktizide und akarizide | |
| 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 | |
| DE2304848A1 (de) | Thionophosphorsaeureoximderivate, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide | |
| DE2220629B2 (de) | Benzisoxazolo(thiono)phosphor(phosphon)säureester, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Insektizide und Akarizide | |
| DE2357526C2 (de) | O-Phenylthionothiolphosphorsäureester, 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 | |
| DE2243370A1 (de) | Thionophosphor(phosphon)-saeureoximderivate, verfahren zu ihrer herstellung und ihre verwendung als insektizide | |
| DE2431849A1 (de) | N-dithiophosphoryl-carbaminsaeureester, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide | |
| DE2202855C3 (de) | Dichlorvinylthionophosphorsäurediesteramide, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Insektizide und Akarizide | |
| DE2360548C3 (de) | 2-Cyanophenyldithiophosphorsäureester, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide und Akarizide | |
| DE2241625A1 (de) | Halogenalkylthionophosphorsaeureester, verfahren zu ihrer herstellung und ihre verwendung als insektizide und nematizide | |
| CH618324A5 (US06826419-20041130-M00005.png) | ||
| DE2225873A1 (de) | Isocyandiphenylaether | |
| DE2403711C2 (de) | O-Triazolylthionophosphor(phosphon)-säureester, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide und Akarizide | |
| DE2010889A1 (de) | S-Alkylmercaptomethyl-thio- bzw.-dithiophosphor(phosphon)-säureester, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Insektizide und Akarizide | |
| DE2258805C3 (de) | N-Methyl-O-phenyl-carbaminsäureester, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung von Insekten | |
| DE2419624A1 (de) | 0-aethyl-0-iso-butyl-0-(2,2-dichlorvinyl)thionophosphorsaeureester, verfahren zu seiner herstellung sowie seine verwendung als insektizid | |
| DE2242135A1 (de) | (thiono)phosphor(phosphon)-saeureester-benzaldoxime, verfahren zu ihrer herstellung sowie ihre verwendung als insektizide und akarizide | |
| 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 | |
| DE2217571A1 (de) | Thionaphthenyl-thiono-alkanphosphonsaeureester, verfahren zu ihrer herstellung und ihre verwendung als insektizide, akarizide und nematizide | |
| DE1815939A1 (de) | 1-Cyan-vinyl-phosphorsaeureester und Verfahren zu ihrer Herstellung | |
| DE2049814A1 (de) | 0,0-Dialkyl-S-phenyl-dithiophosphorsäureester, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Insektizide | |
| DE2528692A1 (de) | Pyridazinyl(thiono)phosphorsaeureester, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide | |
| DE2218102A1 (de) | Naphthisoxazol-thionophosphorsaeureester, verfahren zu ihrer herstellung und ihre verwendung als insektizide, akarizide und larvizide |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| OHN | Withdrawal |