IL34950A - Esters of thiazolo-phosphoric and -phosphonic,thiazolo-thionophosphoric and -thionophosphonic acid,their preparation and use as insecticides and acaricides - Google Patents
Esters of thiazolo-phosphoric and -phosphonic,thiazolo-thionophosphoric and -thionophosphonic acid,their preparation and use as insecticides and acaricidesInfo
- Publication number
- IL34950A IL34950A IL34950A IL3495070A IL34950A IL 34950 A IL34950 A IL 34950A IL 34950 A IL34950 A IL 34950A IL 3495070 A IL3495070 A IL 3495070A IL 34950 A IL34950 A IL 34950A
- Authority
- IL
- Israel
- Prior art keywords
- compound
- formula
- thiazolo
- admixture
- active
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 16
- 150000002148 esters Chemical class 0.000 title claims description 8
- 230000000895 acaricidal effect Effects 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title description 14
- 239000002917 insecticide Substances 0.000 title description 3
- 239000000642 acaricide Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 84
- 239000002904 solvent Substances 0.000 claims description 18
- -1 ester halide Chemical class 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 16
- 239000003085 diluting agent Substances 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
- 241000607479 Yersinia pestis Species 0.000 claims description 11
- 230000006378 damage Effects 0.000 claims description 9
- 241000238631 Hexapoda Species 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 241000233866 Fungi Species 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 4
- 230000000855 fungicidal effect Effects 0.000 claims description 4
- 230000000749 insecticidal effect Effects 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 4
- 150000007979 thiazole derivatives Chemical class 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000004094 surface-active agent Substances 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- WFNBZLITOZFWMW-UHFFFAOYSA-N 5-phenylsulfanyl-1,3-thiazole Chemical compound C1(=CC=CC=C1)SC1=CN=CS1 WFNBZLITOZFWMW-UHFFFAOYSA-N 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 241001465754 Metazoa Species 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- 239000000243 solution Substances 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 10
- 241000255925 Diptera Species 0.000 description 10
- 230000000694 effects Effects 0.000 description 8
- 239000003995 emulsifying agent Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 241000257159 Musca domestica Species 0.000 description 7
- 241000238876 Acari Species 0.000 description 6
- 241000256118 Aedes aegypti Species 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 241000500437 Plutella xylostella Species 0.000 description 5
- 241001454293 Tetranychus urticae Species 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- 241001124076 Aphididae Species 0.000 description 4
- 240000007124 Brassica oleracea Species 0.000 description 4
- 241000254173 Coleoptera Species 0.000 description 4
- 241000721621 Myzus persicae Species 0.000 description 4
- 241001454295 Tetranychidae Species 0.000 description 4
- 238000003197 gene knockdown Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 229920000151 polyglycol Polymers 0.000 description 4
- 239000010695 polyglycol Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 241001510109 Blaberus giganteus Species 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 241000488583 Panonychus ulmi Species 0.000 description 3
- 244000046052 Phaseolus vulgaris Species 0.000 description 3
- 241000254179 Sitophilus granarius Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 230000000361 pesticidal effect Effects 0.000 description 3
- 239000011120 plywood Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 241001143309 Acanthoscelides obtectus Species 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 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
- 235000011303 Brassica alboglabra Nutrition 0.000 description 2
- 235000011302 Brassica oleracea Nutrition 0.000 description 2
- 241001444260 Brassicogethes aeneus Species 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- 241001664260 Byturus tomentosus Species 0.000 description 2
- 241000257163 Calliphora vicina Species 0.000 description 2
- 241000255579 Ceratitis capitata Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241001327638 Cimex lectularius Species 0.000 description 2
- 241000256059 Culex pipiens Species 0.000 description 2
- 241000256113 Culicidae Species 0.000 description 2
- 241000255601 Drosophila melanogaster Species 0.000 description 2
- 241001581006 Dysaphis plantaginea Species 0.000 description 2
- 241000483001 Euproctis chrysorrhoea Species 0.000 description 2
- 239000004606 Fillers/Extenders Substances 0.000 description 2
- 241000255896 Galleria mellonella Species 0.000 description 2
- 241001251909 Hyalopterus pruni Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241000257303 Hymenoptera Species 0.000 description 2
- 241000258916 Leptinotarsa decemlineata Species 0.000 description 2
- 241000255685 Malacosoma neustria Species 0.000 description 2
- 241000254099 Melolontha melolontha Species 0.000 description 2
- 241000721623 Myzus 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
- 241000238675 Periplaneta americana Species 0.000 description 2
- 241001608567 Phaedon cochleariae Species 0.000 description 2
- 241001396980 Phytonemus pallidus Species 0.000 description 2
- 241000255969 Pieris brassicae Species 0.000 description 2
- 241000500439 Plutella Species 0.000 description 2
- 241000952063 Polyphagotarsonemus latus Species 0.000 description 2
- 241000722238 Pseudococcus maritimus Species 0.000 description 2
- 241001509967 Reticulitermes flavipes Species 0.000 description 2
- 241000125167 Rhopalosiphum padi Species 0.000 description 2
- 241001510241 Rhyparobia Species 0.000 description 2
- 235000001537 Ribes X gardonianum Nutrition 0.000 description 2
- 235000001535 Ribes X utile Nutrition 0.000 description 2
- 235000016919 Ribes petraeum Nutrition 0.000 description 2
- 244000281247 Ribes rubrum Species 0.000 description 2
- 235000002355 Ribes spicatum Nutrition 0.000 description 2
- 241000254154 Sitophilus zeamais Species 0.000 description 2
- 241000256251 Spodoptera frugiperda Species 0.000 description 2
- 241001177161 Stegobium paniceum Species 0.000 description 2
- 241001494115 Stomoxys calcitrans Species 0.000 description 2
- 241000254109 Tenebrio molitor Species 0.000 description 2
- 241001414989 Thysanoptera Species 0.000 description 2
- 241000267822 Trogoderma granarium Species 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 238000010410 dusting Methods 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 238000009736 wetting Methods 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
- 241000238818 Acheta domesticus Species 0.000 description 1
- 241000253994 Acyrthosiphon pisum 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
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241001414900 Anopheles stephensi Species 0.000 description 1
- 241000239290 Araneae 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
- 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
- 241000907225 Bruchidius Species 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- IVHVNMLJNASKHW-UHFFFAOYSA-M Chlorphonium chloride Chemical compound [Cl-].CCCC[P+](CCCC)(CCCC)CC1=CC=C(Cl)C=C1Cl IVHVNMLJNASKHW-UHFFFAOYSA-M 0.000 description 1
- 241000254137 Cicadidae Species 0.000 description 1
- 241001415288 Coccidae Species 0.000 description 1
- 241001465977 Coccoidea Species 0.000 description 1
- 241001479447 Coccus hesperidum Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 241001094913 Cryptomyzus Species 0.000 description 1
- 241000289763 Dasygaster padockina Species 0.000 description 1
- 241001641895 Dermestes Species 0.000 description 1
- 241001513837 Dermestes maculatus Species 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- 241001425477 Dysdercus Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000630736 Ephestia Species 0.000 description 1
- 241000122098 Ephestia kuehniella Species 0.000 description 1
- 241001675057 Gastrophysa viridula Species 0.000 description 1
- 241000238821 Gryllus Species 0.000 description 1
- 241000258937 Hemiptera Species 0.000 description 1
- 241000652697 Henschoutedenia flexivitta Species 0.000 description 1
- 241001659689 Hercinothrips Species 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
- 241000721703 Lymantria dispar Species 0.000 description 1
- 241000721715 Macrosiphum Species 0.000 description 1
- 241000721714 Macrosiphum euphorbiae Species 0.000 description 1
- 241000555303 Mamestra brassicae Species 0.000 description 1
- 241000332345 Myzus cerasi Species 0.000 description 1
- 241000961933 Nephotettix virescens Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000238887 Ornithodoros Species 0.000 description 1
- 241001481099 Ornithodoros turicata Species 0.000 description 1
- 241000238814 Orthoptera Species 0.000 description 1
- 241000131101 Oryzaephilus surinamensis Species 0.000 description 1
- 241001548358 Parapiesma quadratum Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 241000257149 Phormia Species 0.000 description 1
- 241000257186 Phormia regina Species 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- 241000690748 Piesma Species 0.000 description 1
- 241001290151 Prunus avium subsp. avium Species 0.000 description 1
- 235000005805 Prunus cerasus Nutrition 0.000 description 1
- 241001097374 Pselliopus cinctus Species 0.000 description 1
- 241000722249 Rhodnius prolixus Species 0.000 description 1
- 241001510236 Rhyparobia maderae Species 0.000 description 1
- 241000985245 Spodoptera litura Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 241001454294 Tetranychus Species 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 241001238452 Tortrix Species 0.000 description 1
- 241001238451 Tortrix viridana 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
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000019693 cherries Nutrition 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- YOTYACDLQWHLDM-UHFFFAOYSA-N ethoxy(propan-2-yl)phosphinic acid Chemical compound CCOP(O)(=O)C(C)C YOTYACDLQWHLDM-UHFFFAOYSA-N 0.000 description 1
- 239000000194 fatty acid Substances 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
- 235000013312 flour Nutrition 0.000 description 1
- 238000003958 fumigation Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000001418 larval effect Effects 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 201000004792 malaria Diseases 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 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
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- PYODKQIVQIVELM-UHFFFAOYSA-M sodium;2,3-bis(2-methylpropyl)naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CC(C)C)C(CC(C)C)=CC2=C1 PYODKQIVQIVELM-UHFFFAOYSA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having alternatively specified atoms bound to the phosphorus atom and not covered by a single one of groups A01N57/10, A01N57/18, A01N57/26, A01N57/34
- A01N57/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having alternatively specified atoms bound to the phosphorus atom and not covered by a single one of groups A01N57/10, A01N57/18, A01N57/26, A01N57/34 containing heterocyclic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/36—Sulfur atoms
-
- 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
- C07F9/6536—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and sulfur atoms with or without oxygen atoms, as the only ring hetero atoms
- C07F9/6539—Five-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Molecular Biology (AREA)
- Agronomy & Crop Science (AREA)
- Biochemistry (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691942013 DE1942013C3 (de) | 1969-08-19 | Thiazolo-(thiono)phosphor(phosphon)säureester, Verfahren zu ihrer Herstellung und diese enthaltende Mittel |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL34950A0 IL34950A0 (en) | 1970-09-17 |
| IL34950A true IL34950A (en) | 1973-01-30 |
Family
ID=5743133
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL34950A IL34950A (en) | 1969-08-19 | 1970-07-17 | Esters of thiazolo-phosphoric and -phosphonic,thiazolo-thionophosphoric and -thionophosphonic acid,their preparation and use as insecticides and acaricides |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3687963A (de) |
| JP (1) | JPS503376B1 (de) |
| BE (1) | BE755027A (de) |
| CA (1) | CA918666A (de) |
| CH (1) | CH532615A (de) |
| ES (1) | ES382817A1 (de) |
| FR (1) | FR2059009A5 (de) |
| GB (1) | GB1275694A (de) |
| IL (1) | IL34950A (de) |
| NL (1) | NL7012194A (de) |
| ZA (1) | ZA705067B (de) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2193021A1 (en) * | 1972-07-19 | 1974-02-15 | Aries Robert | Heterocyclyl-(thio)phosphates - as insecticides and fungicides prepd. from hydroxy thiol derivs. of heterocyclic moiety with corresp. (thio)phosphoric acid chloride |
| FR2249091B1 (de) * | 1973-10-25 | 1978-11-17 | Roussel Uclaf | |
| US3988444A (en) * | 1974-01-08 | 1976-10-26 | Roussel-Uclaf | Novel thiazole derivatives as insecticides and acaricides |
| FR2256924B1 (de) * | 1974-01-08 | 1976-10-08 | Roussel Uclaf | |
| JPS5362164U (de) * | 1976-10-29 | 1978-05-26 | ||
| US4188299A (en) * | 1978-05-17 | 1980-02-12 | Standard Oil Company (Indiana) | Oil soluble dithiophosphoric acid derivatives of mercaptothiadiazoles |
| JPS5741299U (de) * | 1980-08-20 | 1982-03-05 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3574223A (en) * | 1968-03-15 | 1971-04-06 | Ansul Co | 5-substituted-0,0-dialkyl-s -((1,2,4-thiadi-azol - 3 - yl) methyl) phosphorothioates and -dithioates |
-
0
- BE BE755027D patent/BE755027A/xx unknown
-
1970
- 1970-07-17 IL IL34950A patent/IL34950A/en unknown
- 1970-07-23 ZA ZA705067A patent/ZA705067B/xx unknown
- 1970-07-24 CH CH1128270A patent/CH532615A/de not_active IP Right Cessation
- 1970-07-31 CA CA089681A patent/CA918666A/en not_active Expired
- 1970-08-13 US US63614A patent/US3687963A/en not_active Expired - Lifetime
- 1970-08-17 GB GB39547/70A patent/GB1275694A/en not_active Expired
- 1970-08-17 JP JP45071453A patent/JPS503376B1/ja active Pending
- 1970-08-18 NL NL7012194A patent/NL7012194A/xx unknown
- 1970-08-18 ES ES382817A patent/ES382817A1/es not_active Expired
- 1970-08-19 FR FR7030519A patent/FR2059009A5/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH532615A (de) | 1973-01-15 |
| CA918666A (en) | 1973-01-09 |
| NL7012194A (de) | 1971-02-23 |
| FR2059009A5 (de) | 1971-05-28 |
| ZA705067B (en) | 1971-04-28 |
| ES382817A1 (es) | 1972-11-16 |
| GB1275694A (en) | 1972-05-24 |
| DE1942013A1 (de) | 1971-03-04 |
| DE1942013B2 (de) | 1977-04-14 |
| IL34950A0 (en) | 1970-09-17 |
| BE755027A (fr) | 1971-02-19 |
| JPS503376B1 (de) | 1975-02-04 |
| US3687963A (en) | 1972-08-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3801679A (en) | N-(dimethylaminomethylidene)thiol-(thiono)-phosphoric acid ester imides s | |
| IL43548A (en) | N-methyl-n-(n-methylbenzenesulfonamido)-sulphenyl carbamate esters and oximes their preparation and insecticidal and acaricidal compositions containing them | |
| IL46172A (en) | Pyrimidine Acid Esters - Olephosphoric Theones, Their Preparation and Use as Insecticides and Mites | |
| IL34950A (en) | Esters of thiazolo-phosphoric and -phosphonic,thiazolo-thionophosphoric and -thionophosphonic acid,their preparation and use as insecticides and acaricides | |
| IL47958A (en) | Pyrimidinylthionophosphonic acid esters process for their preparation and insecticidal acaricidal and nematicidal compositions containing them | |
| IL34985A (en) | Triazolothiazole esters of phosphoric, phosphonic and phosphonic acids and of the appropriate tionic acids, their preparation and use as insecticides and acaricides | |
| IL29504A (en) | 3,5,6-trichloropyridyl-2-thionophosphonic acid esters | |
| IL31318A (en) | Phosphoric,phosphonic or thionophosphoric(-phosphonic)acid esters of pyridazinediol,their preparation and pest control compositions containing them | |
| US4001404A (en) | N-dithiophosphoryl-carbamic acid esters | |
| IL37223A (en) | Esters of O-pyrazolo-pyrimidine- (thionic) - phosphorous and phosphonic acids, their preparation and use as insecticides and mites | |
| IL31640A (en) | Thionophosphonic acid esters,their preparation and use for pest control | |
| IL43979A (en) | O-triazolylthionophosphoric acid esters and esteramides,their preparation and their use as insecticides and acaricides | |
| US3894020A (en) | 3,4,-Dihydro-4-oxo-quinazolin (3)-yl-(thiono)-phosphoric (phosphonic) acid esters | |
| US3706820A (en) | S-alkylmercaptomethylthiophosphoric or phosphonic acid esters | |
| IL46198A (en) | Triazolothiazolyl-(thiono)-phosphoric (phosphonic)- acid esters their preparation and insecticidal and acaricidal compositions containing them | |
| IL33731A (en) | O,o-dialkyl-s-(1,2,2-trichloroethyl)-thionothiolphosphoric acid esters and o-alkyl-s-(1,2,2-trichloroethyl)-alkane-thionothiolphosphonic acid esters,their preparation and use as insecticides | |
| IL34101A (en) | O-alkyl-s-(n,n-dialkylaminocarbamyl)-methyl-n-monoalkylamido-thiolphosphoric and thionothiolphosphoric acid esters,their preparation and use as insecticides and acaricides | |
| IL32650A (en) | Thionophosphonic acid esters,their preparation and use for combatting insects | |
| US3966920A (en) | O,S-Dialkyl-O-(2-cyanophenyl)-thionothiolphosphoric acid esters and insecticidal and acaricidal compositions and method | |
| IL47240A (en) | O-triazolyl-(thiono)-phosphoric(phosphonic phosphinic) acid esters and ester-amides their preparation and their use as insecticides acaricides or nematicides | |
| US3733378A (en) | Amido-o-lower alkyl-s-allylmercapto-methylthiolphosphoric acid esters | |
| IL41933A (en) | Disubstituted n-(aminomethylene)-thiolphosphoric and thiono-phosphoric acid ester amides their production and their use as insecticides and acaricides | |
| US3862271A (en) | O-alkyl-(thiono) thiol-s-(s-alkylmercapto-s-benzylmercapto-methyl)-phosphoric (phosphonic) acid esters | |
| IL33871A (en) | Phosphoric,phosphonic,thiono-phosphoric and thiono-phosphonic acid esters,their production and their use as insecticides or acaricides | |
| US4013795A (en) | Combating pests with dichlorovinylthionophosphoric acid ester amides |