DE2458329A1 - S-(phenoxymethyl)-dithiophosphorsaeureesteramide, verfahren zu ihrer herstellung sowie ihre verwendung als insektizide, akarizide und nematizide - Google Patents
S-(phenoxymethyl)-dithiophosphorsaeureesteramide, verfahren zu ihrer herstellung sowie ihre verwendung als insektizide, akarizide und nematizideInfo
- Publication number
- DE2458329A1 DE2458329A1 DE19742458329 DE2458329A DE2458329A1 DE 2458329 A1 DE2458329 A1 DE 2458329A1 DE 19742458329 DE19742458329 DE 19742458329 DE 2458329 A DE2458329 A DE 2458329A DE 2458329 A1 DE2458329 A1 DE 2458329A1
- Authority
- DE
- Germany
- Prior art keywords
- spec
- propyl
- aryl
- phenoxymethyl
- iso
- 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 11
- 239000005645 nematicide Substances 0.000 title claims description 6
- 239000000642 acaricide Substances 0.000 title claims description 4
- 239000002917 insecticide Substances 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title description 5
- UBKPIJNLAWHZAA-UHFFFAOYSA-N dihydroxy-(phenoxymethylsulfanyl)-sulfanylidene-$l^{5}-phosphane Chemical compound OP(O)(=S)SCOC1=CC=CC=C1 UBKPIJNLAWHZAA-UHFFFAOYSA-N 0.000 title 1
- 239000000460 chlorine Substances 0.000 claims description 32
- -1 S- (phenoxymethyl) -dithiophosphoric acid ester amides Chemical class 0.000 claims description 25
- 239000002904 solvent Substances 0.000 claims description 19
- 241000244206 Nematoda Species 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 13
- 230000000895 acaricidal effect Effects 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 241000238876 Acari Species 0.000 claims description 5
- 241000607479 Yersinia pestis Species 0.000 claims description 5
- 230000000749 insecticidal effect Effects 0.000 claims description 5
- 239000004606 Fillers/Extenders Substances 0.000 claims description 4
- 241000238631 Hexapoda Species 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 125000005059 halophenyl group Chemical group 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 description 39
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000003995 emulsifying agent Substances 0.000 description 11
- 230000006378 damage Effects 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 238000009472 formulation Methods 0.000 description 8
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 7
- 229920000151 polyglycol Polymers 0.000 description 7
- 239000010695 polyglycol Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 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
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical group CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
- 125000002877 alkyl aryl group Chemical group 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 4
- 240000007124 Brassica oleracea Species 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 230000001069 nematicidal effect Effects 0.000 description 4
- 230000003071 parasitic effect Effects 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 241000254173 Coleoptera Species 0.000 description 3
- 206010061217 Infestation Diseases 0.000 description 3
- 241000243786 Meloidogyne incognita Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 241001608567 Phaedon cochleariae Species 0.000 description 3
- 244000046052 Phaseolus vulgaris Species 0.000 description 3
- 241001454294 Tetranychus Species 0.000 description 3
- 241001454293 Tetranychus urticae Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 241001143309 Acanthoscelides obtectus Species 0.000 description 2
- 241001124076 Aphididae Species 0.000 description 2
- 235000011303 Brassica alboglabra Nutrition 0.000 description 2
- 235000011302 Brassica oleracea Nutrition 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000399949 Ditylenchus dipsaci Species 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 241000258937 Hemiptera Species 0.000 description 2
- 241000379510 Heterodera schachtii Species 0.000 description 2
- 241000257303 Hymenoptera Species 0.000 description 2
- 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 2
- 240000008415 Lactuca sativa Species 0.000 description 2
- 235000003228 Lactuca sativa Nutrition 0.000 description 2
- 241000257166 Lucilia cuprina 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
- 241000721623 Myzus Species 0.000 description 2
- 241000721621 Myzus persicae Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 241001608568 Phaedon Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 241001454295 Tetranychidae Species 0.000 description 2
- 239000000370 acceptor Substances 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 244000078703 ectoparasite Species 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 230000003032 phytopathogenic effect Effects 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000011435 rock Substances 0.000 description 2
- 230000000391 smoking effect Effects 0.000 description 2
- 239000007787 solid 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
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- RKRXQENZBZNFTH-UHFFFAOYSA-N 1,2,3,4,5-pentachloro-6-(chloromethoxy)benzene Chemical compound ClCOC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl RKRXQENZBZNFTH-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 class CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- XMSIHVLSCFVOOP-UHFFFAOYSA-N 4-chloro-1-[4-chloro-2-(chloromethyl)phenoxy]-2-(chloromethyl)benzene Chemical compound ClCC1=CC(Cl)=CC=C1OC1=CC=C(Cl)C=C1CCl XMSIHVLSCFVOOP-UHFFFAOYSA-N 0.000 description 1
- 241000934064 Acarus siro 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
- 241000256111 Aedes <genus> Species 0.000 description 1
- 241000902874 Agelastica alni Species 0.000 description 1
- 241001136265 Agriotes Species 0.000 description 1
- 241000218473 Agrotis Species 0.000 description 1
- 241000411449 Anobium punctatum Species 0.000 description 1
- 241000256186 Anopheles <genus> Species 0.000 description 1
- 241001427556 Anoplura Species 0.000 description 1
- 241000254177 Anthonomus Species 0.000 description 1
- 241001640910 Anthrenus Species 0.000 description 1
- 241001414828 Aonidiella aurantii Species 0.000 description 1
- 241000134843 Aphelenchoides besseyi Species 0.000 description 1
- 241000294568 Aphelenchoides fragariae Species 0.000 description 1
- 241000680417 Aphelenchoides ritzemabosi Species 0.000 description 1
- 241001425390 Aphis fabae Species 0.000 description 1
- 241001600408 Aphis gossypii Species 0.000 description 1
- 241001095118 Aphis pomi Species 0.000 description 1
- 241000239223 Arachnida Species 0.000 description 1
- 241000239290 Araneae Species 0.000 description 1
- 241001162025 Archips podana Species 0.000 description 1
- 241001480754 Argas reflexus Species 0.000 description 1
- 241000722823 Armadillidium Species 0.000 description 1
- 241000238421 Arthropoda Species 0.000 description 1
- 241000387321 Aspidiotus nerii Species 0.000 description 1
- 241000131286 Attagenus Species 0.000 description 1
- 241001490249 Bactrocera oleae Species 0.000 description 1
- 241000254127 Bemisia tabaci Species 0.000 description 1
- 241001142392 Bibio Species 0.000 description 1
- 241001573716 Blaniulus guttulatus Species 0.000 description 1
- 241000238662 Blatta orientalis Species 0.000 description 1
- 241000238657 Blattella germanica Species 0.000 description 1
- 241000256593 Brachycaudus schwartzi 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
- 241000982105 Brevicoryne brassicae Species 0.000 description 1
- 241000398201 Bryobia praetiosa Species 0.000 description 1
- 241001517925 Bucculatrix Species 0.000 description 1
- 241001491790 Bupalus piniaria Species 0.000 description 1
- 241000257163 Calliphora vicina Species 0.000 description 1
- 241001350371 Capua Species 0.000 description 1
- 241001221118 Cecidophyopsis ribis Species 0.000 description 1
- 241000255579 Ceratitis capitata Species 0.000 description 1
- 241000426499 Chilo Species 0.000 description 1
- 241000258920 Chilopoda Species 0.000 description 1
- 241000255942 Choristoneura fumiferana Species 0.000 description 1
- 235000007516 Chrysanthemum Nutrition 0.000 description 1
- 244000189548 Chrysanthemum x morifolium Species 0.000 description 1
- 241001327638 Cimex lectularius Species 0.000 description 1
- 241001427559 Collembola Species 0.000 description 1
- 241000683561 Conoderus Species 0.000 description 1
- 241001212534 Cosmopolites sordidus Species 0.000 description 1
- 241000500845 Costelytra zealandica Species 0.000 description 1
- 241001094916 Cryptomyzus ribis Species 0.000 description 1
- 241000256054 Culex <genus> Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241001635274 Cydia pomonella Species 0.000 description 1
- 206010011732 Cyst Diseases 0.000 description 1
- 241001481695 Dermanyssus gallinae Species 0.000 description 1
- 241001124144 Dermaptera Species 0.000 description 1
- 241001641895 Dermestes Species 0.000 description 1
- 241000489975 Diabrotica Species 0.000 description 1
- 241000258963 Diplopoda Species 0.000 description 1
- 241000511318 Diprion Species 0.000 description 1
- 241000255925 Diptera Species 0.000 description 1
- 241000399934 Ditylenchus Species 0.000 description 1
- 241000255601 Drosophila melanogaster Species 0.000 description 1
- 241001425477 Dysdercus Species 0.000 description 1
- 241000353522 Earias insulana Species 0.000 description 1
- 241000995023 Empoasca Species 0.000 description 1
- 241000630736 Ephestia Species 0.000 description 1
- 241000462639 Epilachna varivestis Species 0.000 description 1
- 241000917107 Eriosoma lanigerum Species 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 241000060469 Eupoecilia ambiguella Species 0.000 description 1
- 241000483001 Euproctis chrysorrhoea Species 0.000 description 1
- 241000515838 Eurygaster Species 0.000 description 1
- 241000239245 Euscelis Species 0.000 description 1
- 241001585293 Euxoa Species 0.000 description 1
- 241000371383 Fannia Species 0.000 description 1
- 241000233488 Feltia Species 0.000 description 1
- 241000720914 Forficula auricularia Species 0.000 description 1
- 235000016623 Fragaria vesca Nutrition 0.000 description 1
- 240000009088 Fragaria x ananassa Species 0.000 description 1
- 235000011363 Fragaria x ananassa Nutrition 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 241000255896 Galleria mellonella Species 0.000 description 1
- 241000723283 Geophilus carpophagus Species 0.000 description 1
- 241001043186 Gibbium Species 0.000 description 1
- 241001442497 Globodera rostochiensis Species 0.000 description 1
- 241001243091 Gryllotalpa Species 0.000 description 1
- 241000256257 Heliothis Species 0.000 description 1
- 241001659688 Hercinothrips femoralis Species 0.000 description 1
- 241001480224 Heterodera Species 0.000 description 1
- 241001466007 Heteroptera Species 0.000 description 1
- 241000957299 Homona magnanima Species 0.000 description 1
- 241001417351 Hoplocampa Species 0.000 description 1
- 241001251909 Hyalopterus pruni Species 0.000 description 1
- 241000832180 Hylotrupes bajulus Species 0.000 description 1
- 241001508566 Hypera postica Species 0.000 description 1
- 241000257176 Hypoderma <fly> Species 0.000 description 1
- 241001149911 Isopoda Species 0.000 description 1
- 241000256602 Isoptera Species 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241001470017 Laodelphax striatella Species 0.000 description 1
- 241000256686 Lasius <genus> Species 0.000 description 1
- 241000238866 Latrodectus mactans Species 0.000 description 1
- 241000255777 Lepidoptera Species 0.000 description 1
- 241000500881 Lepisma Species 0.000 description 1
- 241000258916 Leptinotarsa decemlineata Species 0.000 description 1
- 241000254023 Locusta Species 0.000 description 1
- 241000257162 Lucilia <blowfly> Species 0.000 description 1
- 241001177134 Lyctus Species 0.000 description 1
- 241000721696 Lymantria Species 0.000 description 1
- 241000255685 Malacosoma neustria Species 0.000 description 1
- 241000555303 Mamestra brassicae Species 0.000 description 1
- 241001415013 Melanoplus Species 0.000 description 1
- 241001143352 Meloidogyne Species 0.000 description 1
- 241000243784 Meloidogyne arenaria Species 0.000 description 1
- 241000243785 Meloidogyne javanica Species 0.000 description 1
- 241000254099 Melolontha melolontha Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000952627 Monomorium pharaonis 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
- 241000358422 Nephotettix cincticeps Species 0.000 description 1
- 241001556089 Nilaparvata lugens Species 0.000 description 1
- 241001385056 Niptus hololeucus Species 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- 241000384103 Oniscus asellus Species 0.000 description 1
- 241000963703 Onychiurus armatus Species 0.000 description 1
- 241001491877 Operophtera brumata Species 0.000 description 1
- 241000238890 Ornithodoros moubata Species 0.000 description 1
- 241000238814 Orthoptera Species 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 241000131101 Oryzaephilus surinamensis Species 0.000 description 1
- 241000975417 Oscinella frit Species 0.000 description 1
- 241001147398 Ostrinia nubilalis Species 0.000 description 1
- 241000486438 Panolis flammea Species 0.000 description 1
- 241000488581 Panonychus citri Species 0.000 description 1
- 241000488583 Panonychus ulmi Species 0.000 description 1
- 241001148650 Paratylenchus Species 0.000 description 1
- 241001450657 Parthenolecanium corni Species 0.000 description 1
- 241000721451 Pectinophora gossypiella Species 0.000 description 1
- 241000517306 Pediculus humanus corporis Species 0.000 description 1
- 241000721454 Pemphigus Species 0.000 description 1
- 241000238675 Periplaneta americana Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 241001401861 Phorodon humuli Species 0.000 description 1
- 241001525654 Phyllocnistis citrella Species 0.000 description 1
- 241000497192 Phyllocoptruta oleivora Species 0.000 description 1
- 241001517955 Phyllonorycter blancardella Species 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- 241000255972 Pieris <butterfly> Species 0.000 description 1
- 241000690748 Piesma Species 0.000 description 1
- 241000500437 Plutella xylostella Species 0.000 description 1
- 241000908127 Porcellio scaber Species 0.000 description 1
- 241000193943 Pratylenchus Species 0.000 description 1
- 108010009736 Protein Hydrolysates Proteins 0.000 description 1
- 235000005805 Prunus cerasus Nutrition 0.000 description 1
- 241000722234 Pseudococcus Species 0.000 description 1
- 241000526145 Psylla Species 0.000 description 1
- 241001160824 Psylliodes Species 0.000 description 1
- 241001105129 Ptinus Species 0.000 description 1
- 241000201377 Radopholus Species 0.000 description 1
- 241001509970 Reticulitermes <genus> Species 0.000 description 1
- 241000864202 Rhipicephalus evertsi Species 0.000 description 1
- 241000238680 Rhipicephalus microplus Species 0.000 description 1
- 241000722249 Rhodnius prolixus Species 0.000 description 1
- 241000125167 Rhopalosiphum padi Species 0.000 description 1
- 241001510236 Rhyparobia maderae Species 0.000 description 1
- 241000318997 Rhyzopertha dominica Species 0.000 description 1
- 241000855013 Rotylenchus Species 0.000 description 1
- 241000316887 Saissetia oleae Species 0.000 description 1
- 241000509427 Sarcoptes scabiei Species 0.000 description 1
- 241000253973 Schistocerca gregaria Species 0.000 description 1
- 241000522594 Scorpio maurus Species 0.000 description 1
- 241001157779 Scutigera Species 0.000 description 1
- 241001313237 Scutigerella immaculata Species 0.000 description 1
- 241000258242 Siphonaptera Species 0.000 description 1
- 241000180219 Sitobion avenae Species 0.000 description 1
- 241000254181 Sitophilus Species 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 241000256248 Spodoptera Species 0.000 description 1
- 241000256247 Spodoptera exigua Species 0.000 description 1
- 241000985245 Spodoptera litura Species 0.000 description 1
- 241001494115 Stomoxys calcitrans Species 0.000 description 1
- 241000883295 Symphyla Species 0.000 description 1
- 241000254109 Tenebrio molitor Species 0.000 description 1
- 241001065719 Tetranychus ludeni Species 0.000 description 1
- 241000339374 Thrips tabaci Species 0.000 description 1
- 241001414989 Thysanoptera Species 0.000 description 1
- 241000511627 Tipula paludosa Species 0.000 description 1
- 241001238451 Tortrix viridana Species 0.000 description 1
- 241000018137 Trialeurodes vaporariorum Species 0.000 description 1
- 241001414833 Triatoma Species 0.000 description 1
- 241000254086 Tribolium <beetle> Species 0.000 description 1
- 241000255993 Trichoplusia ni Species 0.000 description 1
- 241000267823 Trogoderma Species 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical group ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 241001274788 Viteus vitifoliae Species 0.000 description 1
- 241000353223 Xenopsylla cheopis Species 0.000 description 1
- 241000201423 Xiphinema Species 0.000 description 1
- 241001466337 Yponomeuta Species 0.000 description 1
- 241001414985 Zygentoma Species 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 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
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 244000000054 animal parasite Species 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 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
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 208000031513 cyst Diseases 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
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 238000005516 engineering process Methods 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
- 230000002349 favourable effect Effects 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- 239000008187 granular material Substances 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
- 229920005610 lignin Polymers 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N methyl iso-propyl ketone Natural products CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 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
- 244000052769 pathogen Species 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 239000003531 protein hydrolysate Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 150000003839 salts Chemical group 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003580 thiophosphoric acid esters Chemical class 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 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
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
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
- C07F9/2404—Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/2408—Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic of hydroxyalkyl compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (19)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19742458329 DE2458329A1 (de) | 1974-12-10 | 1974-12-10 | S-(phenoxymethyl)-dithiophosphorsaeureesteramide, verfahren zu ihrer herstellung sowie ihre verwendung als insektizide, akarizide und nematizide |
GB44297/75A GB1501944A (en) | 1974-12-10 | 1975-10-28 | S-(halophenoxymethyl)-dithiophosphoric acid ester-amides process for their preparation and their use as insecticides acaracides and nematocides |
PL1975185358A PL96682B1 (pl) | 1974-12-10 | 1975-12-08 | Srodek owadobojczy,roztoczobojczy i nicieniobojczy |
US05/638,875 US4036947A (en) | 1974-12-10 | 1975-12-08 | O-Alkyl-N-subustituted-S-halophenoxymethyl-dithiophosphoric acid ester-amides |
IL48612A IL48612A0 (en) | 1974-12-10 | 1975-12-08 | S-(phenoxymethyl)-dithiophosphoric acid esteramides,their preparation and their use as insecticides,acaricides and nematocides |
SU7502195711A SU577938A3 (ru) | 1974-12-10 | 1975-12-08 | Способ борьбы с насекомыми, клещами и нематодами |
AU87332/75A AU8733275A (en) | 1974-12-10 | 1975-12-08 | S-%phenoxymethyl<-dithiophosphoric acid ester amides |
BE162520A BE836371A (fr) | 1974-12-10 | 1975-12-08 | Nouveaux amides d'esters d'acides s-(phenoxymethyl)-dithiophosphoriques, leur procede de preparation et leur application comme insecticides, acaricides et nematicides |
JP50145187A JPS5231055A (en) | 1974-12-10 | 1975-12-08 | Process for preparing ss*phenoxymethyl** dithiophosphate esteramid |
BR7508114*A BR7508114A (pt) | 1974-12-10 | 1975-12-08 | Processo para preparar amidas de esteres de acido s-(fenoximetil)-ditiofosforico,bem como composicoes inseticidas,acaricidas ou nematocidas a base destas |
DD189965A DD125570A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-12-10 | 1975-12-08 | |
JP50145188A JPS5182731A (en) | 1974-12-10 | 1975-12-08 | Satsukonchu satsudani oyobi satsusenchuzai |
ZA757692A ZA757692B (en) | 1974-12-10 | 1975-12-09 | S-(phenoxymethyl)-dithiophosphoric acid ester-amides,process for their preparation and their use as insecticides,acaracides and nematocides |
ES443309A ES443309A1 (es) | 1974-12-10 | 1975-12-09 | Procedimiento para la obtencion de amidas de esteres de aci-dos s-(fenoximetil)-ditiofosforicos. |
DK557875A DK557875A (da) | 1974-12-10 | 1975-12-09 | S-(phenoxymethyl)-dithiophosphor-syreesteramider, fremgangsmade til fremstilling deraf samt deres anvendelse som insecticider, acaricider og nematodicider |
NL7514332A NL7514332A (nl) | 1974-12-10 | 1975-12-09 | S-(fenoxymethyl)-dithiofosforzuuresteramiden, werkwijze ter bereiding daarvan alsmede werkwijze voor de toepassing daarvan als insecticiden, acar- iciden en nematiciden. |
TR18506A TR18506A (tr) | 1974-12-10 | 1975-12-09 | S-(fenoksimetil)-ditiofosforik asit ester amidleri,bunlarin hazirlanisi icin usul ve bunlarin ensektisidler,akarisiddler ve nematosidler olarak kullanilmalari |
AT937175A AT336640B (de) | 1974-12-10 | 1975-12-10 | Verfahren zur herstellung von neuen s-(phenoxymethyl)-dithiophosphorsaureesteramiden |
FR7537787A FR2294180A1 (fr) | 1974-12-10 | 1975-12-10 | Nouveaux amides d'esters d'acides s-(phenoxymethyl)-dithiophosphoriques, leur procede de preparation et leur application comme insecticides, acaricides et nematicides |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19742458329 DE2458329A1 (de) | 1974-12-10 | 1974-12-10 | S-(phenoxymethyl)-dithiophosphorsaeureesteramide, verfahren zu ihrer herstellung sowie ihre verwendung als insektizide, akarizide und nematizide |
Publications (1)
Publication Number | Publication Date |
---|---|
DE2458329A1 true DE2458329A1 (de) | 1976-06-16 |
Family
ID=5933038
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19742458329 Pending DE2458329A1 (de) | 1974-12-10 | 1974-12-10 | S-(phenoxymethyl)-dithiophosphorsaeureesteramide, verfahren zu ihrer herstellung sowie ihre verwendung als insektizide, akarizide und nematizide |
Country Status (18)
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IT1128783B (it) * | 1980-05-05 | 1986-06-04 | Fiat Auto Spa | Generatore autonomo di energia elettrica |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3165545A (en) * | 1962-07-09 | 1965-01-12 | Dow Chemical Co | S-aryl phosphoramidodithioates |
US3368002A (en) * | 1964-06-12 | 1968-02-06 | Stauffer Chemical Co | S-chlorophenoxymethyl thio, dithio phosphonates or phosphates |
DE2034475C3 (de) * | 1970-07-11 | 1979-02-22 | Bayer Ag, 5090 Leverkusen | O-AlkyKAJkenyl, AJkinyD-S-alkyl (alkenyl-alkinyl)-N-monoalkyl-(alkenyl, alkinyl)- thionothiolphosphorsäureesteramide, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Nematozide, Insektizide und Akarizide |
-
1974
- 1974-12-10 DE DE19742458329 patent/DE2458329A1/de active Pending
-
1975
- 1975-10-28 GB GB44297/75A patent/GB1501944A/en not_active Expired
- 1975-12-08 BE BE162520A patent/BE836371A/xx unknown
- 1975-12-08 DD DD189965A patent/DD125570A5/xx unknown
- 1975-12-08 JP JP50145187A patent/JPS5231055A/ja active Pending
- 1975-12-08 JP JP50145188A patent/JPS5182731A/ja active Pending
- 1975-12-08 BR BR7508114*A patent/BR7508114A/pt unknown
- 1975-12-08 SU SU7502195711A patent/SU577938A3/ru active
- 1975-12-08 AU AU87332/75A patent/AU8733275A/en not_active Expired
- 1975-12-08 IL IL48612A patent/IL48612A0/xx unknown
- 1975-12-08 PL PL1975185358A patent/PL96682B1/pl unknown
- 1975-12-08 US US05/638,875 patent/US4036947A/en not_active Expired - Lifetime
- 1975-12-09 TR TR18506A patent/TR18506A/xx unknown
- 1975-12-09 ZA ZA757692A patent/ZA757692B/xx unknown
- 1975-12-09 NL NL7514332A patent/NL7514332A/xx unknown
- 1975-12-09 DK DK557875A patent/DK557875A/da unknown
- 1975-12-09 ES ES443309A patent/ES443309A1/es not_active Expired
- 1975-12-10 AT AT937175A patent/AT336640B/de not_active IP Right Cessation
- 1975-12-10 FR FR7537787A patent/FR2294180A1/fr not_active Withdrawn
Also Published As
Publication number | Publication date |
---|---|
GB1501944A (en) | 1978-02-22 |
DK557875A (da) | 1976-06-11 |
NL7514332A (nl) | 1976-06-14 |
US4036947A (en) | 1977-07-19 |
FR2294180A1 (fr) | 1976-07-09 |
BE836371A (fr) | 1976-06-08 |
ATA937175A (de) | 1976-09-15 |
SU577938A3 (ru) | 1977-10-25 |
AT336640B (de) | 1977-05-10 |
TR18506A (tr) | 1977-03-04 |
JPS5231055A (en) | 1977-03-09 |
DD125570A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-05-04 |
IL48612A0 (en) | 1976-02-29 |
JPS5182731A (en) | 1976-07-20 |
ZA757692B (en) | 1976-11-24 |
ES443309A1 (es) | 1977-04-16 |
BR7508114A (pt) | 1976-08-24 |
AU8733275A (en) | 1977-06-16 |
PL96682B1 (pl) | 1978-01-31 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
DE3317824A1 (de) | Phosphorsaeureester | |
EP0000887B1 (de) | Cyclopropylsubstituierte Pyrimidin(4)yl(thiono)-(thiol)-phosphor(phosphon)-säureester bzw. -esteramide, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide und Akarizide | |
DE2450951A1 (de) | Pyrimidinyl(thiono)(thiol)phosphor (phosphon)-saeureester bzw. -esteramide, verfahren zu ihrer herstellung und ihre verwendung als insektizide, akarizide und nematizide | |
DE2831852A1 (de) | 2-cyclopropyl-pyrimidin(4)yl-(thiono)(thiol)-phosphor-(phosphon)-saeureester bzw. -esteramide, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel | |
DE2703712A1 (de) | Substituierte pyrimidinon eckige klammer auf (di)-thio eckige klammer zu -phosphor-(phosphon)-saeureester bzw. -esteramide, verfahren zu ihrer herstellung und ihre verwendung als insektizide, akarizide und nematizide | |
DE2545392A1 (de) | Benzimidoylthionothiolphosphorsaeureester, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide | |
DE2639258A1 (de) | Tert.-butyl-substituierte pyrazolyl (thiono)(thiol)-phosphor(phosphon)-saeureester bzw. -esteramide, verfahren zu ihrer herstellung und ihre verwendung als insektizide, akarizide und nematizide | |
DE2629016C2 (de) | O-(1-Fluor-2-halogen-äthyl)(thiono) phosphor(phosphon)-säureesteramide, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide, Akarizide und Nematizide | |
DE2501769A1 (de) | Substituierte pyrimidinyl(thiono)(thiol)-phosphor (phosphon)-saeureester, verfahren zu ihrer herstellung sowie ihre verwendung als insektizide, akarizide und nematozide | |
CH635350A5 (de) | Substituierte pyrimidinyl(thio)-phosphor(phosphon)-saeureester bzw. -esteramide, verfahren zu ihrer herstellung und ihre verwendung als insektizide, akarizide und nematizide. | |
EP0012344B1 (de) | O-Pyrazol(4)yl-O-äthyl-S-n-propyl-(thiono)thiol-phosphorsäureester, Verfahren zu ihrer Herstellung und ihre Verwendung als Schädlingsbekämpfungsmittel | |
DE2630561A1 (de) | 1-fluor-2-halogen-aethyl-thionophosphor (phosphon)-saeureester, verfahren zu ihrer herstellung und ihre verwendung als insektizide, akarizide und nematizide | |
DE2446218C2 (de) | Pyridazinyl(thiono)(thiol)phosphor (phosphon)-säureester und -esteramide, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide und Akarizide | |
DE3126390A1 (de) | S-azolyl-methyl-di(tri)-thiophosphorsaeureester, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel | |
EP0000388B1 (de) | Pyridazinon(thiono)-phosphorsäureester, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide und Akarizide | |
DE2814984A1 (de) | Pyrimidin(5)yl-(thiono)(thiol)- phosphor(phosphon)-saeureester bzw. -esteramide, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide | |
DE2455763A1 (de) | O-vinylthiono(thiol)phosphor(phosphon)-saeureester, verfahren zu ihrer herstellung und ihre verwendung als insektizide | |
DE2458329A1 (de) | S-(phenoxymethyl)-dithiophosphorsaeureesteramide, verfahren zu ihrer herstellung sowie ihre verwendung als insektizide, akarizide und nematizide | |
DE2507702A1 (de) | Pyrimidin(2)yl-thionophosphorsaeureester, verfahren zu ihrer herstellung sowie ihre verwendung als insektizide und akarizide | |
DE3445465A1 (de) | Pyrimidinyl-thionophosphorsaeureester | |
CH621794A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
DE2714038A1 (de) | Trifluormethylsulfonylphenylthiono (thiol)phosphorsaeureester bzw. -esteramide, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide | |
DE2510138A1 (de) | S-(trifluorchloraethylmercapto)- aethyl(thiono)-(di)thiolphosphor(phosphon)- saeureester bzw. -esteramide, verfahren zu ihrer herstellung sowie ihre verwendung als insektizide, akarizide und nematizide | |
DE2445555A1 (de) | S- eckige klammer auf isoureidocarbonylmethyl eckige klammer zu-(thiono) (di)thiolphosphor(phosphon)-saeureester bzw. -esteramide, verfahren zu ihrer herstellung sowie ihre verwendung als insektizide und akarizide | |
DE2639256A1 (de) | Alkoxy- bzw. alkylthiosubstituierte pyrimidin(thiono)-(thiol)-phosphor(phosphon)-saeureester, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide |