DE2217571A1 - Thionaphthenyl-thiono-alkanphosphonsaeureester, verfahren zu ihrer herstellung und ihre verwendung als insektizide, akarizide und nematizide - Google Patents
Thionaphthenyl-thiono-alkanphosphonsaeureester, verfahren zu ihrer herstellung und ihre verwendung als insektizide, akarizide und nematizideInfo
- Publication number
- DE2217571A1 DE2217571A1 DE2217571A DE2217571A DE2217571A1 DE 2217571 A1 DE2217571 A1 DE 2217571A1 DE 2217571 A DE2217571 A DE 2217571A DE 2217571 A DE2217571 A DE 2217571A DE 2217571 A1 DE2217571 A1 DE 2217571A1
- Authority
- DE
- Germany
- Prior art keywords
- thionaphthenyl
- active ingredient
- thiono
- compounds according
- insecticides
- 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 9
- 239000002917 insecticide Substances 0.000 title claims description 4
- 239000005645 nematicide Substances 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title description 5
- 239000000642 acaricide Substances 0.000 title description 3
- 239000002253 acid Substances 0.000 claims description 20
- 238000002360 preparation method Methods 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 12
- 241000238631 Hexapoda Species 0.000 claims description 11
- 150000002148 esters Chemical class 0.000 claims description 10
- 230000000749 insecticidal effect Effects 0.000 claims description 8
- 241000238876 Acari Species 0.000 claims description 7
- 230000000895 acaricidal effect Effects 0.000 claims description 7
- 241000607479 Yersinia pestis Species 0.000 claims description 5
- 239000004606 Fillers/Extenders Substances 0.000 claims description 4
- 239000000370 acceptor Substances 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 150000003863 ammonium salts Chemical class 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 241000341511 Nematodes Species 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 description 45
- 239000002904 solvent Substances 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- 239000003995 emulsifying agent Substances 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- -1 alkyl radicals Chemical class 0.000 description 12
- 239000002689 soil Substances 0.000 description 12
- 239000000203 mixture Substances 0.000 description 9
- 241000255925 Diptera Species 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 125000002877 alkyl aryl group Chemical group 0.000 description 7
- 241001124076 Aphididae Species 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 240000007124 Brassica oleracea Species 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000012141 concentrate Substances 0.000 description 6
- 229920000151 polyglycol Polymers 0.000 description 6
- 239000010695 polyglycol Substances 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical group CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
- 241000721621 Myzus persicae Species 0.000 description 5
- 241000244206 Nematoda Species 0.000 description 5
- 244000046052 Phaseolus vulgaris Species 0.000 description 5
- 230000006378 damage Effects 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 4
- 241001454295 Tetranychidae Species 0.000 description 4
- 241001454293 Tetranychus urticae Species 0.000 description 4
- 238000006243 chemical reaction Methods 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
- 230000001069 nematicidal effect 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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 235000011303 Brassica alboglabra Nutrition 0.000 description 3
- 235000011302 Brassica oleracea Nutrition 0.000 description 3
- 241000254173 Coleoptera Species 0.000 description 3
- 206010061217 Infestation Diseases 0.000 description 3
- 241001465754 Metazoa Species 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
- 150000002170 ethers Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 241001510109 Blaberus giganteus Species 0.000 description 2
- 241000238662 Blatta orientalis Species 0.000 description 2
- 241000256593 Brachycaudus schwartzi Species 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
- 241000256059 Culex pipiens Species 0.000 description 2
- 241001414892 Delia radicum Species 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000255581 Drosophila <fruit fly, genus> Species 0.000 description 2
- 241000255601 Drosophila melanogaster 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
- 240000008415 Lactuca sativa Species 0.000 description 2
- 235000003228 Lactuca sativa Nutrition 0.000 description 2
- 241000721703 Lymantria dispar Species 0.000 description 2
- 241001143352 Meloidogyne 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
- 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
- 241000238814 Orthoptera Species 0.000 description 2
- 241000488583 Panonychus ulmi Species 0.000 description 2
- 241001396980 Phytonemus pallidus Species 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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 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
- 241000254179 Sitophilus granarius Species 0.000 description 2
- 241000254154 Sitophilus zeamais Species 0.000 description 2
- 244000061456 Solanum tuberosum Species 0.000 description 2
- 235000002595 Solanum tuberosum Nutrition 0.000 description 2
- 241001177161 Stegobium paniceum Species 0.000 description 2
- 241001454294 Tetranychus Species 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 239000003610 charcoal 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
- 239000003085 diluting agent Substances 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 125000001806 thionaphthenyl group Chemical group 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical class CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- 241001143309 Acanthoscelides obtectus 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
- 241000426834 Aegina Species 0.000 description 1
- 241001136265 Agriotes Species 0.000 description 1
- 241000218475 Agrotis segetum Species 0.000 description 1
- 241000449794 Alabama argillacea Species 0.000 description 1
- 241000489242 Amphitetranychus viennensis Species 0.000 description 1
- 241001414900 Anopheles stephensi Species 0.000 description 1
- 241001425390 Aphis fabae Species 0.000 description 1
- 241000239290 Araneae 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
- 241001470771 Athous haemorrhoidalis Species 0.000 description 1
- 206010004194 Bed bug infestation Diseases 0.000 description 1
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- 241000238788 Blaberus craniifer Species 0.000 description 1
- 241001674044 Blattodea Species 0.000 description 1
- 240000002791 Brassica napus 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
- 235000004977 Brassica sinapistrum 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
- 241001221118 Cecidophyopsis ribis Species 0.000 description 1
- 241000255579 Ceratitis capitata Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000254137 Cicadidae Species 0.000 description 1
- 241001327638 Cimex lectularius Species 0.000 description 1
- 241001414835 Cimicidae 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
- 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
- 241001581006 Dysaphis plantaginea Species 0.000 description 1
- 241001425477 Dysdercus Species 0.000 description 1
- 241000630736 Ephestia Species 0.000 description 1
- 241001221110 Eriophyidae 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
- 241000652697 Henschoutedenia flexivitta Species 0.000 description 1
- 241001659688 Hercinothrips femoralis Species 0.000 description 1
- 241001251909 Hyalopterus pruni Species 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
- 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
- 241000961933 Nephotettix virescens Species 0.000 description 1
- 241001491877 Operophtera brumata Species 0.000 description 1
- 241000238887 Ornithodoros 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
- 240000002834 Paulownia tomentosa Species 0.000 description 1
- 235000010678 Paulownia tomentosa Nutrition 0.000 description 1
- 241000238675 Periplaneta americana Species 0.000 description 1
- 241001608567 Phaedon cochleariae Species 0.000 description 1
- 241000257149 Phormia Species 0.000 description 1
- 241000690748 Piesma Species 0.000 description 1
- 241000952063 Polyphagotarsonemus latus Species 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
- 241001092459 Rubus Species 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
- 240000006394 Sorghum bicolor Species 0.000 description 1
- 241000256251 Spodoptera frugiperda Species 0.000 description 1
- 241000985245 Spodoptera litura 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
- 241001414831 Triatoma infestans 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
- 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
- 239000013543 active substance Substances 0.000 description 1
- 150000001298 alcohols Chemical class 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
- 235000012211 aluminium silicate Nutrition 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
- 244000309466 calf Species 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000012876 carrier material Substances 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
- 239000004927 clay Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 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
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 235000013601 eggs Nutrition 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
- AIJQQTBLBLBZDI-UHFFFAOYSA-N ethoxy-ethyl-hydroxy-sulfanylidene-$l^{5}-phosphane Chemical compound CCOP(O)(=S)CC AIJQQTBLBLBZDI-UHFFFAOYSA-N 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000002191 fatty alcohols Chemical class 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
- 239000007789 gas Substances 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
- 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
- 229910052500 inorganic mineral Inorganic materials 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
- 201000004792 malaria Diseases 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
- 239000011707 mineral Substances 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000003921 oil 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
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 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
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 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
- 230000000391 smoking effect Effects 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
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003860 storage 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
- 239000002699 waste material Substances 0.000 description 1
- 235000020681 well water Nutrition 0.000 description 1
- 239000002349 well water Substances 0.000 description 1
- 239000002023 wood 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms
- C07F9/655345—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms the sulfur atom being part of a five-membered ring
- C07F9/655354—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms the sulfur atom being part of a five-membered ring condensed with carbocyclic rings or carbocyclic ring systems
-
- 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
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
- A01N57/24—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing heterocyclic radicals
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Dentistry (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2217571A DE2217571A1 (de) | 1972-04-12 | 1972-04-12 | Thionaphthenyl-thiono-alkanphosphonsaeureester, verfahren zu ihrer herstellung und ihre verwendung als insektizide, akarizide und nematizide |
| IL41985A IL41985A0 (en) | 1972-04-12 | 1973-04-09 | Thionaphthenyl-thiono-alkanephosphonic acid esters,their production and their use as insecticides,acaricides and acaricides |
| NL7305068A NL7305068A (fr) | 1972-04-12 | 1973-04-11 | |
| BR732610A BR7302610D0 (pt) | 1972-04-12 | 1973-04-11 | Processo para a preparacao de ester de acido tionaftenil- tiono-alcanofosfonico e composicoes inseticidas, acaricidas e nematocidas a base deste |
| ZA732513A ZA732513B (en) | 1972-04-12 | 1973-04-11 | Thionophthenyl-thiono-alkanephosphonic acid esters,process for their production and their use as insecticides,acaricides and nematocides |
| BE129922A BE798115A (fr) | 1972-04-12 | 1973-04-12 | Nouveaux esters d'acides thionaphtenylthiono-alcane-phosphoniques |
| JP48040940A JPS497437A (fr) | 1972-04-12 | 1973-04-12 | |
| JP48040939A JPS497269A (fr) | 1972-04-12 | 1973-04-12 | |
| FR7313250A FR2180028A1 (en) | 1972-04-12 | 1973-04-12 | O-alkyl-o-(benzothiophen-3-yl) alkylthiophosphonates - - with insecticidal, acaricidal and nematocidal activity |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2217571A DE2217571A1 (de) | 1972-04-12 | 1972-04-12 | Thionaphthenyl-thiono-alkanphosphonsaeureester, verfahren zu ihrer herstellung und ihre verwendung als insektizide, akarizide und nematizide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2217571A1 true DE2217571A1 (de) | 1973-10-18 |
Family
ID=5841719
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2217571A Pending DE2217571A1 (de) | 1972-04-12 | 1972-04-12 | Thionaphthenyl-thiono-alkanphosphonsaeureester, verfahren zu ihrer herstellung und ihre verwendung als insektizide, akarizide und nematizide |
Country Status (8)
| Country | Link |
|---|---|
| JP (2) | JPS497269A (fr) |
| BE (1) | BE798115A (fr) |
| BR (1) | BR7302610D0 (fr) |
| DE (1) | DE2217571A1 (fr) |
| FR (1) | FR2180028A1 (fr) |
| IL (1) | IL41985A0 (fr) |
| NL (1) | NL7305068A (fr) |
| ZA (1) | ZA732513B (fr) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5148437A (ja) * | 1974-10-18 | 1976-04-26 | Nihon Nohyaku Co Ltd | Satsukonchusatsudanizai oyobi sonoseizohoho |
-
1972
- 1972-04-12 DE DE2217571A patent/DE2217571A1/de active Pending
-
1973
- 1973-04-09 IL IL41985A patent/IL41985A0/xx unknown
- 1973-04-11 NL NL7305068A patent/NL7305068A/xx unknown
- 1973-04-11 BR BR732610A patent/BR7302610D0/pt unknown
- 1973-04-11 ZA ZA732513A patent/ZA732513B/xx unknown
- 1973-04-12 JP JP48040939A patent/JPS497269A/ja active Pending
- 1973-04-12 JP JP48040940A patent/JPS497437A/ja active Pending
- 1973-04-12 BE BE129922A patent/BE798115A/fr unknown
- 1973-04-12 FR FR7313250A patent/FR2180028A1/fr not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| NL7305068A (fr) | 1973-10-16 |
| ZA732513B (en) | 1974-02-27 |
| JPS497269A (fr) | 1974-01-22 |
| IL41985A0 (en) | 1973-06-29 |
| BE798115A (fr) | 1973-10-12 |
| BR7302610D0 (pt) | 1974-07-18 |
| JPS497437A (fr) | 1974-01-23 |
| FR2180028A1 (en) | 1973-11-23 |
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 | |
| DE2214059A1 (de) | Halogenphenyl-pyridazino-thionophosphor (phosphon)-saeureester, verfahren zu ihrer herstellung sowie ihre verwendung als insektizide | |
| DE2440677A1 (de) | Pyrimidinylthionophosphonsaeureester, verfahren zu ihrer herstellung und ihre verwendung als insektizide, akarizide und nematizide | |
| DE2132938A1 (de) | 0-pyrazolothionophosphor(phosphon)saeureester, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide | |
| DE2220629A1 (de) | Benzisoxazolo(thiono)phosphor(phosphon)saeureester, verfahren zu ihrer herstellung sowie ihre verwendung als insektizide und akarizide | |
| CH621129A5 (fr) | ||
| DE2361451C2 (de) | Triazolothiazolyl-(thiono)-phosphor (phosphon)-säureester, Verfahren zu ihrer Herstellung sowie ihre Verwendung zur Bekämpfung von Insekten, Milben und Zecken | |
| DE2304062C2 (de) | 0-Aryl-thionoalkanphosphonsäureesterimidderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide, Akarizide und Nematizide | |
| DE2211338B2 (de) | N-(Aminomethyliden)-thiol-phosphorsäureesterimide, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide und Akarizide | |
| DE2033947A1 (de) | 0 Pyrazolopynmidin (thiono) phosphor (phosphon)saureester, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Insek tizide und Akanzide | |
| DE2049813A1 (de) | Pyndazinothionophosphor(phosphon) säureester, Verfahren zu ihrer Herstel lung sowie ihre Verwendung als Insek tizide und Akanzide | |
| 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 | |
| DE2010889A1 (de) | S-Alkylmercaptomethyl-thio- bzw.-dithiophosphor(phosphon)-säureester, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Insektizide und Akarizide | |
| DE2217571A1 (de) | Thionaphthenyl-thiono-alkanphosphonsaeureester, verfahren zu ihrer herstellung und ihre verwendung als insektizide, akarizide und nematizide | |
| DE2241395B2 (de) | 0-Pyrazolopyrimidin-(thiono)-phosphor (phosphon)-säureester, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Insektizide und Akarizide | |
| DE2350631A1 (de) | Triazolothiazol-(thiono)-phosphor(phosphon)-saeureester, verfahren zu ihrer herstellung sowie ihre verwendung als insektizide und akarizide | |
| DE2031750A1 (de) | Benzisoxazolo(thiono)phosphor(phosphon)-säureester, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Insektizide und Akarizide | |
| 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 | |
| DE2532628A1 (de) | Fluorsubstituierte carbaminylmethyldithioalkanphosphonsaeureester, verfahren zu ihrer herstellung sowie ihre verwendung als insektizide, akarizide und nematizide | |
| DE1941705A1 (de) | Thiol- bzw. Thionothiolphosphor- oder -phosphonsaeureester,Verfahren zu ihrer Herstellung sowie ihre Verwendung als Insektizide und Akarizide | |
| DE2528692A1 (de) | Pyridazinyl(thiono)phosphorsaeureester, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide | |
| DE2202528A1 (de) | Jodphenyl(thiono)-phosphor(phosphon)saeureester, -esteramide und -esterdiamide, verfahren zu ihrer herstellung sowie ihre verwendung als insektizide und akarizide | |
| DE2050090A1 (de) | Thionophosphor(phosphon)-säureesterformaldoxime, ein Verfahren zu ihrer Herstellung sowie ihre Verwendung als Insektizide und Akarizide |