IL36221A - Esters of phosphoric acid, their preparation and use as pesticides - Google Patents
Esters of phosphoric acid, their preparation and use as pesticidesInfo
- Publication number
- IL36221A IL36221A IL36221A IL3622171A IL36221A IL 36221 A IL36221 A IL 36221A IL 36221 A IL36221 A IL 36221A IL 3622171 A IL3622171 A IL 3622171A IL 36221 A IL36221 A IL 36221A
- Authority
- IL
- Israel
- Prior art keywords
- compound
- formula
- reaction
- process according
- atom
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 15
- 150000003014 phosphoric acid esters Chemical class 0.000 title claims description 6
- 239000000575 pesticide Substances 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims description 81
- 238000000034 method Methods 0.000 claims description 29
- 239000000203 mixture Substances 0.000 claims description 21
- 241000238631 Hexapoda Species 0.000 claims description 19
- 239000003085 diluting agent Substances 0.000 claims description 13
- 241000244206 Nematoda Species 0.000 claims description 10
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical group OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 238000009835 boiling Methods 0.000 claims description 6
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 4
- 239000011230 binding agent Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 239000007800 oxidant agent Substances 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 230000001069 nematicidal effect Effects 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 230000000895 acaricidal effect Effects 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 230000000749 insecticidal effect Effects 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 241001474033 Acar Species 0.000 claims 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 26
- 230000000694 effects Effects 0.000 description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- -1 alkyl sulfonyl radical Chemical class 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000009472 formulation Methods 0.000 description 8
- 239000002917 insecticide Substances 0.000 description 8
- 239000003995 emulsifying agent Substances 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000010998 test method Methods 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000000969 carrier Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 235000013601 eggs Nutrition 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- 241000238876 Acari Species 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 241000255777 Lepidoptera Species 0.000 description 3
- 241000243785 Meloidogyne javanica Species 0.000 description 3
- 241000721621 Myzus persicae Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000003905 agrochemical Substances 0.000 description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 3
- 239000013011 aqueous formulation Substances 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 235000012730 carminic acid Nutrition 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- LCCNCVORNKJIRZ-UHFFFAOYSA-N parathion Chemical compound CCOP(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 LCCNCVORNKJIRZ-UHFFFAOYSA-N 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000726760 Cadra cautella Species 0.000 description 2
- RZXLPPRPEOUENN-UHFFFAOYSA-N Chlorfenson Chemical compound C1=CC(Cl)=CC=C1OS(=O)(=O)C1=CC=C(Cl)C=C1 RZXLPPRPEOUENN-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241000289763 Dasygaster padockina Species 0.000 description 2
- 239000004606 Fillers/Extenders Substances 0.000 description 2
- 244000017020 Ipomoea batatas Species 0.000 description 2
- 235000002678 Ipomoea batatas Nutrition 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 241000256250 Spodoptera littoralis Species 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 125000004432 carbon atom Chemical group C* 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
- 239000000428 dust Substances 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
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 230000001976 improved effect Effects 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 229920005610 lignin Polymers 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000005645 nematicide Substances 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- KNMQFZVRVIGMPA-UHFFFAOYSA-N 1,3-dichloropropa-1,2-diene Chemical group ClC=C=CCl KNMQFZVRVIGMPA-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 compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- GJQBCYNBOOLTBZ-UHFFFAOYSA-N 2,4-dichloro-3-phenylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(Cl)C(C=2C=CC=CC=2)=C1Cl GJQBCYNBOOLTBZ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- 102100027522 Baculoviral IAP repeat-containing protein 7 Human genes 0.000 description 1
- 101710177963 Baculoviral IAP repeat-containing protein 7 Proteins 0.000 description 1
- YWUQCBSWCDTGAW-UHFFFAOYSA-N C(C)O[ClH]P(=S)(Cl)[ClH]C1=C(C=C(C=C1)[N+](=O)[O-])Cl Chemical compound C(C)O[ClH]P(=S)(Cl)[ClH]C1=C(C=C(C=C1)[N+](=O)[O-])Cl YWUQCBSWCDTGAW-UHFFFAOYSA-N 0.000 description 1
- ZUFPRRMPHVWYDT-UHFFFAOYSA-N C(C)O[ClH]P(=S)(Cl)[ClH]C1=CC2=CC=CC=C2C=C1 Chemical compound C(C)O[ClH]P(=S)(Cl)[ClH]C1=CC2=CC=CC=C2C=C1 ZUFPRRMPHVWYDT-UHFFFAOYSA-N 0.000 description 1
- ITLXXZQXRKUNDC-UHFFFAOYSA-N C(C)O[ClH]P(=S)(Cl)[ClH]C1=CC=C(C=C1)C#N Chemical compound C(C)O[ClH]P(=S)(Cl)[ClH]C1=CC=C(C=C1)C#N ITLXXZQXRKUNDC-UHFFFAOYSA-N 0.000 description 1
- ZBDQNEVQFNTIOJ-UHFFFAOYSA-N C(C)O[ClH]P(=S)(Cl)[ClH]C1=CC=CC=C1 Chemical compound C(C)O[ClH]P(=S)(Cl)[ClH]C1=CC=CC=C1 ZBDQNEVQFNTIOJ-UHFFFAOYSA-N 0.000 description 1
- CHMDYZDHFROBTB-UHFFFAOYSA-N CC#N.CC(C)CC(C)=O Chemical compound CC#N.CC(C)CC(C)=O CHMDYZDHFROBTB-UHFFFAOYSA-N 0.000 description 1
- JFYAQZQNHBDYLJ-UHFFFAOYSA-N CCC(C(CC)=C1Cl)=CC([S+]=P([O-])(O)O)=C1Cl Chemical compound CCC(C(CC)=C1Cl)=CC([S+]=P([O-])(O)O)=C1Cl JFYAQZQNHBDYLJ-UHFFFAOYSA-N 0.000 description 1
- MCAVSDZVXFARQF-UHFFFAOYSA-N CC[ClH]P(Cl)(Cl)=[S+]C1=CC=CC=C1 Chemical compound CC[ClH]P(Cl)(Cl)=[S+]C1=CC=CC=C1 MCAVSDZVXFARQF-UHFFFAOYSA-N 0.000 description 1
- 101100279436 Caenorhabditis elegans egg-2 gene Proteins 0.000 description 1
- 241000254173 Coleoptera Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- 241000255925 Diptera Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241000258937 Hemiptera Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- 241000256602 Isoptera Species 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 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
- 241000819999 Nymphes 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
- 241001249129 Scirpophaga incertulas Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Chemical group 0.000 description 1
- 241001454295 Tetranychidae Species 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 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
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
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- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 230000012447 hatching Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
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- 150000004679 hydroxides Chemical class 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 229910052740 iodine Inorganic materials 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([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
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
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- 229910052901 montmorillonite Inorganic materials 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
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- 235000021278 navy bean Nutrition 0.000 description 1
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- RLBIQVVOMOPOHC-UHFFFAOYSA-N parathion-methyl Chemical compound COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C=C1 RLBIQVVOMOPOHC-UHFFFAOYSA-N 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
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- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- SUVIGLJNEAMWEG-UHFFFAOYSA-N propane-1-thiol Chemical compound CCCS SUVIGLJNEAMWEG-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
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007921 spray Substances 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
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003580 thiophosphoric acid esters Chemical class 0.000 description 1
- JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000004563 wettable powder 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
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/18—Esters of thiophosphoric acids with hydroxyaryl compounds
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
- A01N57/14—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing aromatic radicals
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (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 |
|---|---|---|---|
| JP45020845A JPS4924656B1 (da) | 1970-03-13 | 1970-03-13 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL36221A0 IL36221A0 (en) | 1971-04-28 |
| IL36221A true IL36221A (en) | 1973-08-29 |
Family
ID=12038399
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL36221A IL36221A (en) | 1970-03-13 | 1971-02-17 | Esters of phosphoric acid, their preparation and use as pesticides |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US3825636A (da) |
| JP (1) | JPS4924656B1 (da) |
| AT (1) | AT304934B (da) |
| BE (1) | BE764116A (da) |
| CA (1) | CA922728A (da) |
| CH (1) | CH517782A (da) |
| CS (1) | CS167917B2 (da) |
| DE (1) | DE2111414C3 (da) |
| ES (1) | ES389200A1 (da) |
| FR (1) | FR2081936B1 (da) |
| GB (1) | GB1295418A (da) |
| HU (1) | HU162202B (da) |
| IL (1) | IL36221A (da) |
| NL (1) | NL169881C (da) |
| PL (1) | PL76334B1 (da) |
| RO (1) | RO60626A (da) |
| SU (1) | SU365891A3 (da) |
| TR (1) | TR16921A (da) |
| ZA (1) | ZA711085B (da) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4035488A (en) * | 1971-09-30 | 1977-07-12 | Ciba-Geigy Corporation | Insecticidal and acaricidal substituted phenyl thiophosphoric acid esters |
| US3911122A (en) * | 1971-09-30 | 1975-10-07 | Ciba Geigy Corp | Insecticidal and acarididal substituted phenyl thiophosphoric acid esters |
| US3891728A (en) * | 1971-09-30 | 1975-06-24 | Ciba Geigy Corp | O-alkyl-S-alkyl-O-substituted phenyl-thiophosphoric acid esters |
| US3969444A (en) * | 1972-02-01 | 1976-07-13 | Ciba-Geigy Ag | O,S-dialkyl-O-allylphenyl-thiophosphates and -dithiophosphates |
| US4003964A (en) * | 1972-02-01 | 1977-01-18 | Ciba-Geigy Ag | Phenylene-bis(O,S-dialkylthiophosphates) |
| US3969438A (en) * | 1972-02-01 | 1976-07-13 | Ciba-Geigy Ag | O,S-dialkyl-O-cyanomethylphenylthio-phosphates and -dithiophosphates |
| US3943202A (en) * | 1972-11-03 | 1976-03-09 | Ciba-Geigy Corporation | O-methyl/ethyl-s-propyl/butyl-o-phenyl thiophosphates and dithiophosphates having an ether group or the phenyl ring |
| US3991141A (en) * | 1972-11-03 | 1976-11-09 | Ciba-Geigy Corporation | O-methyl/ethyl-S-propyl/butyl-O-phenyl thiphosphates and dithiophosphates having a thioether group on the phenyl ring |
| US4017612A (en) * | 1972-11-03 | 1977-04-12 | Ciba-Geigy Corporation | Combatting insects and acarids with certain O-methyl/ethyl-S-propyl/butyl-O-phenyl-thiophosphates and -dithiophosphates |
| CA1058192A (en) * | 1972-11-03 | 1979-07-10 | Ciba-Geigy Ag | Esters |
| US4005158A (en) * | 1973-03-15 | 1977-01-25 | Ciba-Geigy Corporation | O-(2-vinylphenyl)-thiol-phosphates |
| DE2355442A1 (de) * | 1973-11-06 | 1975-05-07 | Bayer Ag | 0-aethyl-s-n-propyl-0-(2-brom-4-cyanophenyl)-thionothiolphosphorsaeureester, verfahren zu seiner herstellung und seine verwendung als insektizid und akarizid |
| US4013794A (en) * | 1973-11-17 | 1977-03-22 | Bayer Aktiengesellschaft | O-alkyl-s-alkyl-o-phenyl phosphates and insecticidal and acaricidal method of use |
| DE2360548C3 (de) * | 1973-12-05 | 1981-12-17 | Bayer Ag, 5090 Leverkusen | 2-Cyanophenyldithiophosphorsäureester, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide und Akarizide |
| US4029774A (en) * | 1974-06-26 | 1977-06-14 | Rohm And Haas Company | O,S-dialkyl O -phenylthio-phenyl phosphorothiolates/phosphorodithioates and their derivatives and pesticidal use |
| US4053595A (en) * | 1975-12-11 | 1977-10-11 | Mobay Chemical Corporation | Synergistic composition for the control of insects |
| US4287189A (en) * | 1976-04-26 | 1981-09-01 | Rohm And Haas Company | O,S-Dialkyl O-oxysulfonylphenyl phosphorothiolates and phosphorodithioates |
| DE2625764A1 (de) * | 1976-06-09 | 1977-12-29 | Bayer Ag | Trifluormethylthio-phenyl(di)-thio -phosphorsaeureester, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide |
| US4104376A (en) * | 1977-07-07 | 1978-08-01 | Mobay Chemical Corporation | Synergistic composition for the control of insects |
| US4213975A (en) | 1979-03-23 | 1980-07-22 | The Dow Chemical Company | Insecticidal synergistic mixtures of O,O-diethyl O-(3,5,6-trichloro-2-pyridinyl)phosphorothioate and O-ethyl O-(4-(methylthio)phenyl)-S-n-propyl phosphorothioate |
| JPS55133389A (en) * | 1979-04-03 | 1980-10-17 | Takeda Chem Ind Ltd | Organic phosphoric ester and insecticide comprising it |
| DE3360509D1 (en) * | 1982-04-08 | 1985-09-12 | Basf Ag | Fluoro-ethoxyphenyl-(di)-thiophosphoric-acid esters, process for their preparation and their use as pesticides |
| US4474776A (en) * | 1983-02-16 | 1984-10-02 | Velsicol Chemical Corporation | Anthryl substituted phosphorus compounds as insecticides |
| DE19953775A1 (de) | 1999-11-09 | 2001-05-10 | Bayer Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| DE10015310A1 (de) * | 2000-03-28 | 2001-10-04 | Bayer Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| EP1170322A1 (en) * | 2000-07-04 | 2002-01-09 | ATOFINA Research | Heat sealing polyolefins |
| DE10042736A1 (de) | 2000-08-31 | 2002-03-14 | Bayer Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| DE102007045955A1 (de) | 2007-09-26 | 2009-04-09 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| EP2410847A1 (de) | 2009-03-25 | 2012-02-01 | Bayer CropScience AG | Wirkstoffkombinationen mit insektiziden und akariziden eigenschaften |
-
1970
- 1970-03-13 JP JP45020845A patent/JPS4924656B1/ja active Pending
-
1971
- 1971-02-17 IL IL36221A patent/IL36221A/en unknown
- 1971-02-18 CH CH233271A patent/CH517782A/de not_active IP Right Cessation
- 1971-02-19 ZA ZA711085A patent/ZA711085B/xx unknown
- 1971-03-09 CS CS1721A patent/CS167917B2/cs unknown
- 1971-03-10 US US00123087A patent/US3825636A/en not_active Expired - Lifetime
- 1971-03-10 DE DE2111414A patent/DE2111414C3/de not_active Expired
- 1971-03-10 SU SU1632756A patent/SU365891A3/ru active
- 1971-03-11 BE BE764116A patent/BE764116A/xx not_active IP Right Cessation
- 1971-03-11 HU HUBA2552A patent/HU162202B/hu unknown
- 1971-03-12 FR FR717108805A patent/FR2081936B1/fr not_active Expired
- 1971-03-12 RO RO66243A patent/RO60626A/ro unknown
- 1971-03-12 NL NLAANVRAGE7103349,A patent/NL169881C/xx not_active IP Right Cessation
- 1971-03-12 AT AT215571A patent/AT304934B/de not_active IP Right Cessation
- 1971-03-12 CA CA107558A patent/CA922728A/en not_active Expired
- 1971-03-12 PL PL1971146841A patent/PL76334B1/pl unknown
- 1971-03-13 ES ES389200A patent/ES389200A1/es not_active Expired
- 1971-03-21 TR TR16921A patent/TR16921A/xx unknown
- 1971-04-19 GB GB1295418D patent/GB1295418A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| TR16921A (tr) | 1973-11-01 |
| ZA711085B (en) | 1971-12-29 |
| GB1295418A (da) | 1972-11-08 |
| AT304934B (de) | 1973-01-25 |
| DE2111414B2 (de) | 1979-06-21 |
| NL169881C (nl) | 1982-09-01 |
| US3825636A (en) | 1974-07-23 |
| NL7103349A (da) | 1971-09-15 |
| IL36221A0 (en) | 1971-04-28 |
| HU162202B (da) | 1973-01-29 |
| FR2081936B1 (da) | 1973-06-08 |
| RO60626A (da) | 1976-07-15 |
| CA922728A (en) | 1973-03-13 |
| DE2111414C3 (de) | 1980-06-04 |
| JPS4924656B1 (da) | 1974-06-25 |
| DE2111414A1 (de) | 1971-09-30 |
| BE764116A (fr) | 1971-09-13 |
| PL76334B1 (da) | 1975-02-28 |
| FR2081936A1 (da) | 1971-12-10 |
| CH517782A (de) | 1972-01-15 |
| SU365891A3 (da) | 1973-01-08 |
| CS167917B2 (da) | 1976-05-28 |
| ES389200A1 (es) | 1973-06-16 |
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