IL34101A - O-alkyl-s-(n,n-dialkylaminocarbamyl)-methyl-n-monoalkylamido-thiolphosphoric and thionothiolphosphoric acid esters,their preparation and use as insecticides and acaricides - Google Patents
O-alkyl-s-(n,n-dialkylaminocarbamyl)-methyl-n-monoalkylamido-thiolphosphoric and thionothiolphosphoric acid esters,their preparation and use as insecticides and acaricidesInfo
- Publication number
- IL34101A IL34101A IL34101A IL3410170A IL34101A IL 34101 A IL34101 A IL 34101A IL 34101 A IL34101 A IL 34101A IL 3410170 A IL3410170 A IL 3410170A IL 34101 A IL34101 A IL 34101A
- Authority
- IL
- Israel
- Prior art keywords
- alkyl
- process according
- compounds
- methyl
- reaction
- Prior art date
Links
- 239000002253 acid Substances 0.000 title description 14
- 238000002360 preparation method Methods 0.000 title description 6
- 150000002148 esters Chemical class 0.000 title description 5
- 239000002917 insecticide Substances 0.000 title description 4
- 230000000895 acaricidal effect Effects 0.000 title description 3
- 239000000642 acaricide Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 38
- 238000000034 method Methods 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000003995 emulsifying agent Substances 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 7
- 241000255925 Diptera Species 0.000 description 7
- -1 alkali metal salt Chemical class 0.000 description 7
- 239000003085 diluting agent Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 241000238631 Hexapoda Species 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 241000238876 Acari Species 0.000 description 5
- 241001454293 Tetranychus urticae Species 0.000 description 5
- 241000607479 Yersinia pestis Species 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 241001124076 Aphididae Species 0.000 description 4
- 241000254173 Coleoptera Species 0.000 description 4
- 241000721621 Myzus persicae Species 0.000 description 4
- 244000046052 Phaseolus vulgaris Species 0.000 description 4
- 241001454295 Tetranychidae Species 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 241001510109 Blaberus giganteus Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000257159 Musca domestica Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 241000488583 Panonychus ulmi Species 0.000 description 3
- 241000500437 Plutella xylostella Species 0.000 description 3
- 241000254179 Sitophilus granarius Species 0.000 description 3
- 241000254154 Sitophilus zeamais 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
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 238000011065 in-situ storage Methods 0.000 description 3
- AGUWUIVKDXDKBT-UHFFFAOYSA-N phenyl 2-chloroacetate Chemical compound ClCC(=O)OC1=CC=CC=C1 AGUWUIVKDXDKBT-UHFFFAOYSA-N 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- RHUYHJGZWVXEHW-UHFFFAOYSA-N 1,1-Dimethyhydrazine Chemical compound CN(C)N RHUYHJGZWVXEHW-UHFFFAOYSA-N 0.000 description 2
- 241000238818 Acheta domesticus Species 0.000 description 2
- 241000256118 Aedes aegypti Species 0.000 description 2
- 241001425390 Aphis fabae Species 0.000 description 2
- 241000387321 Aspidiotus nerii Species 0.000 description 2
- 241000238662 Blatta orientalis Species 0.000 description 2
- 241000238657 Blattella germanica Species 0.000 description 2
- 240000007124 Brassica oleracea Species 0.000 description 2
- 241001664260 Byturus tomentosus Species 0.000 description 2
- 241000257163 Calliphora vicina Species 0.000 description 2
- 241001327638 Cimex lectularius Species 0.000 description 2
- 241001465977 Coccoidea Species 0.000 description 2
- 241000256059 Culex pipiens Species 0.000 description 2
- 239000004606 Fillers/Extenders Substances 0.000 description 2
- 241000255896 Galleria mellonella Species 0.000 description 2
- 241000257303 Hymenoptera Species 0.000 description 2
- 241000254099 Melolontha melolontha Species 0.000 description 2
- 241000810465 Myzus cerasi cerasi Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 241001491877 Operophtera brumata Species 0.000 description 2
- 241000131101 Oryzaephilus surinamensis Species 0.000 description 2
- 241000238675 Periplaneta americana Species 0.000 description 2
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 2
- 241001396980 Phytonemus pallidus Species 0.000 description 2
- 241000255969 Pieris brassicae Species 0.000 description 2
- 241000952063 Polyphagotarsonemus latus Species 0.000 description 2
- 241000125167 Rhopalosiphum padi Species 0.000 description 2
- 241001510241 Rhyparobia Species 0.000 description 2
- 235000001537 Ribes X gardonianum Nutrition 0.000 description 2
- 235000001535 Ribes X utile Nutrition 0.000 description 2
- 235000016919 Ribes petraeum Nutrition 0.000 description 2
- 244000281247 Ribes rubrum Species 0.000 description 2
- 235000002355 Ribes spicatum Nutrition 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 241000256251 Spodoptera frugiperda Species 0.000 description 2
- 241001177161 Stegobium paniceum Species 0.000 description 2
- 241001494115 Stomoxys calcitrans Species 0.000 description 2
- 241001238451 Tortrix viridana Species 0.000 description 2
- 241000267822 Trogoderma granarium Species 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 238000007098 aminolysis reaction Methods 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000010410 dusting Methods 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 230000007935 neutral effect Effects 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
- 229920000151 polyglycol Polymers 0.000 description 2
- 239000010695 polyglycol Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- XJRIDJAGAYGJCK-UHFFFAOYSA-N (1-acetyl-5-bromoindol-3-yl) acetate Chemical compound C1=C(Br)C=C2C(OC(=O)C)=CN(C(C)=O)C2=C1 XJRIDJAGAYGJCK-UHFFFAOYSA-N 0.000 description 1
- ZHHHDUSWMATTFE-UHFFFAOYSA-N 1,1-dipropylhydrazine Chemical compound CCCN(N)CCC ZHHHDUSWMATTFE-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 241000253994 Acyrthosiphon pisum Species 0.000 description 1
- 241000426834 Aegina Species 0.000 description 1
- 241001136265 Agriotes Species 0.000 description 1
- 241001136249 Agriotes lineatus Species 0.000 description 1
- 241000218475 Agrotis segetum Species 0.000 description 1
- 241000449794 Alabama argillacea Species 0.000 description 1
- 241001414900 Anopheles stephensi Species 0.000 description 1
- 241000273311 Aphis spiraecola Species 0.000 description 1
- 241000238788 Blaberus craniifer Species 0.000 description 1
- 241001674044 Blattodea Species 0.000 description 1
- 241000256593 Brachycaudus schwartzi Species 0.000 description 1
- 235000011303 Brassica alboglabra Nutrition 0.000 description 1
- 235000011302 Brassica oleracea Nutrition 0.000 description 1
- 241001444260 Brassicogethes aeneus Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 241000907225 Bruchidius Species 0.000 description 1
- 241001221118 Cecidophyopsis ribis Species 0.000 description 1
- 241000255580 Ceratitis <genus> Species 0.000 description 1
- 241000255579 Ceratitis capitata Species 0.000 description 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 1
- 241000254137 Cicadidae Species 0.000 description 1
- 241001415288 Coccidae Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 241001094913 Cryptomyzus Species 0.000 description 1
- 241000254171 Curculionidae Species 0.000 description 1
- 241000289763 Dasygaster padockina Species 0.000 description 1
- 241001641895 Dermestes Species 0.000 description 1
- 241001513837 Dermestes maculatus Species 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- 241000255581 Drosophila <fruit fly, genus> 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
- 241000122098 Ephestia kuehniella Species 0.000 description 1
- 241000483001 Euproctis chrysorrhoea Species 0.000 description 1
- 241000239245 Euscelis Species 0.000 description 1
- 241001675057 Gastrophysa viridula Species 0.000 description 1
- 241000258937 Hemiptera Species 0.000 description 1
- 241000652697 Henschoutedenia flexivitta Species 0.000 description 1
- 241001659688 Hercinothrips femoralis Species 0.000 description 1
- 241001251909 Hyalopterus pruni Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241000256602 Isoptera 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
- 241000721703 Lymantria dispar Species 0.000 description 1
- 241000721715 Macrosiphum Species 0.000 description 1
- 241000721714 Macrosiphum euphorbiae Species 0.000 description 1
- 241000255685 Malacosoma neustria Species 0.000 description 1
- 241000555303 Mamestra brassicae Species 0.000 description 1
- 241000766511 Meligethes Species 0.000 description 1
- 101100412856 Mus musculus Rhod gene Proteins 0.000 description 1
- 241000721623 Myzus Species 0.000 description 1
- 241000961933 Nephotettix virescens Species 0.000 description 1
- 241000238887 Ornithodoros Species 0.000 description 1
- 241001481099 Ornithodoros turicata Species 0.000 description 1
- 241000238814 Orthoptera Species 0.000 description 1
- 241001548358 Parapiesma quadratum Species 0.000 description 1
- 241001608567 Phaedon cochleariae Species 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 241000257149 Phormia Species 0.000 description 1
- 241000257186 Phormia regina Species 0.000 description 1
- 241000690748 Piesma Species 0.000 description 1
- 235000005805 Prunus cerasus Nutrition 0.000 description 1
- 241001097374 Pselliopus cinctus Species 0.000 description 1
- 241000722238 Pseudococcus maritimus Species 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 241001509967 Reticulitermes flavipes Species 0.000 description 1
- 241001350474 Rhopalosiphum nymphaeae Species 0.000 description 1
- 241001510236 Rhyparobia maderae Species 0.000 description 1
- 241000985245 Spodoptera litura Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Chemical group 0.000 description 1
- 241000254109 Tenebrio molitor Species 0.000 description 1
- 241001454294 Tetranychus Species 0.000 description 1
- 101100242191 Tetraodon nigroviridis rho gene Proteins 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
- 241001466337 Yponomeuta Species 0.000 description 1
- 241000064240 Yponomeuta padellus Species 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 229960001701 chloroform Drugs 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 238000003958 fumigation Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 201000004792 malaria Diseases 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
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- XDRROYCELWSRPL-UHFFFAOYSA-N n-[ethoxy(sulfanyl)phosphinothioyl]propan-2-amine Chemical compound CCOP(S)(=S)NC(C)C XDRROYCELWSRPL-UHFFFAOYSA-N 0.000 description 1
- 230000001473 noxious effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen 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
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000126 substance Substances 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
- 230000009885 systemic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 231100000820 toxicity test Toxicity 0.000 description 1
- 238000009834 vaporization 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
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691920503 DE1920503A1 (de) | 1969-04-23 | 1969-04-23 | O-Alkyl-N-monoalkylamido-(thiono)-thiolphosphorsaeure-S-(N,N-dialkylamino-carbamyl)-methylester und Verfahren zu ihrer Herstellung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL34101A0 IL34101A0 (en) | 1970-05-21 |
| IL34101A true IL34101A (en) | 1972-12-29 |
Family
ID=5731987
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL34101A IL34101A (en) | 1969-04-23 | 1970-03-18 | O-alkyl-s-(n,n-dialkylaminocarbamyl)-methyl-n-monoalkylamido-thiolphosphoric and thionothiolphosphoric acid esters,their preparation and use as insecticides and acaricides |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US3705928A (xx) |
| JP (2) | JPS4833731B1 (xx) |
| AT (1) | AT300461B (xx) |
| AU (1) | AU1417170A (xx) |
| BE (1) | BE749407A (xx) |
| BR (1) | BR7017974D0 (xx) |
| CH (1) | CH531834A (xx) |
| DE (1) | DE1920503A1 (xx) |
| DK (1) | DK124210B (xx) |
| ES (1) | ES378966A1 (xx) |
| FR (1) | FR2039414A1 (xx) |
| GB (1) | GB1294183A (xx) |
| IL (1) | IL34101A (xx) |
| NL (1) | NL7005845A (xx) |
| TR (1) | TR16819A (xx) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2240033A1 (de) * | 1972-08-16 | 1974-02-28 | Bayer Ag | S-(alkoxycarbonyl)-alkyl-thiophosphorsaeureesteramide, verfahren zu ihrer herstellung sowie ihre verwendung als insektizide und akarizide |
| JPS53161033U (xx) * | 1977-05-19 | 1978-12-16 | ||
| DE3228631A1 (de) * | 1982-07-31 | 1984-02-02 | Hoechst Ag, 6230 Frankfurt | Neue (di)-thiophosphor- und phosphonsaeure-derivate, verfahren zu ihrer herstellung, sie enthaltende mittel und ihre verwendung im pflanzenschutz |
| US5424333A (en) * | 1985-10-21 | 1995-06-13 | Rohm And Haas Company | Anthelmintic N'-substituted-N,N'-disubstitutedhydrazines |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3518327A (en) * | 1967-04-10 | 1970-06-30 | Stauffer Chemical Co | Phosphoro and phosphono acetylhydrazides |
-
1969
- 1969-04-23 DE DE19691920503 patent/DE1920503A1/de active Pending
-
1970
- 1970-03-16 CH CH391670A patent/CH531834A/de not_active IP Right Cessation
- 1970-03-18 IL IL34101A patent/IL34101A/en unknown
- 1970-04-02 BR BR217974/70A patent/BR7017974D0/pt unknown
- 1970-04-08 TR TR16819A patent/TR16819A/xx unknown
- 1970-04-20 US US30357A patent/US3705928A/en not_active Expired - Lifetime
- 1970-04-21 JP JP45033553A patent/JPS4833731B1/ja active Pending
- 1970-04-21 JP JP45033554A patent/JPS4817059B1/ja active Pending
- 1970-04-22 AU AU14171/70A patent/AU1417170A/en not_active Expired
- 1970-04-22 GB GB09322/70A patent/GB1294183A/en not_active Expired
- 1970-04-22 NL NL7005845A patent/NL7005845A/xx unknown
- 1970-04-22 DK DK204070AA patent/DK124210B/da unknown
- 1970-04-23 FR FR7014917A patent/FR2039414A1/fr not_active Withdrawn
- 1970-04-23 ES ES378966A patent/ES378966A1/es not_active Expired
- 1970-04-23 AT AT372870A patent/AT300461B/de not_active IP Right Cessation
- 1970-04-23 BE BE749407D patent/BE749407A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL7005845A (xx) | 1970-10-27 |
| FR2039414A1 (xx) | 1971-01-15 |
| TR16819A (tr) | 1973-07-01 |
| JPS4833731B1 (xx) | 1973-10-16 |
| CH531834A (de) | 1972-12-31 |
| IL34101A0 (en) | 1970-05-21 |
| ES378966A1 (es) | 1972-08-01 |
| US3705928A (en) | 1972-12-12 |
| BE749407A (fr) | 1970-10-23 |
| AU1417170A (en) | 1971-10-28 |
| AT300461B (de) | 1972-07-25 |
| JPS4817059B1 (xx) | 1973-05-26 |
| DK124210B (da) | 1972-09-25 |
| GB1294183A (en) | 1972-10-25 |
| DE1920503A1 (de) | 1970-11-05 |
| BR7017974D0 (pt) | 1973-06-26 |
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