CH627620A5 - Method and composition for controlling insects and acarids - Google Patents
Method and composition for controlling insects and acarids Download PDFInfo
- Publication number
- CH627620A5 CH627620A5 CH1210277A CH1210277A CH627620A5 CH 627620 A5 CH627620 A5 CH 627620A5 CH 1210277 A CH1210277 A CH 1210277A CH 1210277 A CH1210277 A CH 1210277A CH 627620 A5 CH627620 A5 CH 627620A5
- Authority
- CH
- Switzerland
- Prior art keywords
- insects
- bis
- carbon atoms
- phosphorus compound
- group
- Prior art date
Links
- 241000238631 Hexapoda Species 0.000 title claims description 22
- 238000000034 method Methods 0.000 title claims description 17
- 239000000203 mixture Substances 0.000 title claims description 15
- 235000013601 eggs Nutrition 0.000 claims description 26
- 239000007788 liquid Substances 0.000 claims description 16
- -1 phosphorus compound Chemical class 0.000 claims description 15
- 229910052698 phosphorus Inorganic materials 0.000 claims description 14
- 239000011574 phosphorus Substances 0.000 claims description 13
- 239000007787 solid Substances 0.000 claims description 13
- 239000000460 chlorine Chemical group 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 6
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 239000011593 sulfur Substances 0.000 claims description 6
- 125000001188 haloalkyl group Chemical group 0.000 claims description 5
- 239000000758 substrate Substances 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 230000000749 insecticidal effect Effects 0.000 claims description 4
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 239000002689 soil Substances 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 230000001954 sterilising effect Effects 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 27
- 238000002360 preparation method Methods 0.000 description 23
- 241000196324 Embryophyta Species 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 13
- 239000003053 toxin Substances 0.000 description 13
- 231100000765 toxin Toxicity 0.000 description 13
- 108700012359 toxins Proteins 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 244000046052 Phaseolus vulgaris Species 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000006185 dispersion Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 241000238876 Acari Species 0.000 description 7
- 241000254173 Coleoptera Species 0.000 description 7
- 241000118205 Ovicides Species 0.000 description 7
- 239000000642 acaricide Substances 0.000 description 7
- 230000000895 acaricidal effect Effects 0.000 description 6
- 239000002270 dispersing agent Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- CPSASKRDDKKCJE-UHFFFAOYSA-N 1-chloro-4-[(4-chlorophenyl)-methylphosphoryl]benzene Chemical compound C=1C=C(Cl)C=CC=1P(=O)(C)C1=CC=C(Cl)C=C1 CPSASKRDDKKCJE-UHFFFAOYSA-N 0.000 description 5
- ZDOFKYHAGYDKBL-UHFFFAOYSA-N 1-chloro-4-[chloromethyl-(4-chlorophenyl)phosphoryl]benzene Chemical compound C=1C=C(Cl)C=CC=1P(=O)(CCl)C1=CC=C(Cl)C=C1 ZDOFKYHAGYDKBL-UHFFFAOYSA-N 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000002917 insecticide Substances 0.000 description 5
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 5
- 150000003003 phosphines Chemical class 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- 241000462639 Epilachna varivestis Species 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 235000008504 concentrate Nutrition 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- WSANLGASBHUYGD-UHFFFAOYSA-N sulfidophosphanium Chemical class S=[PH3] WSANLGASBHUYGD-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000003209 petroleum derivative Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 3
- ZSKJUMNEBQQVDZ-UHFFFAOYSA-N 1-chloro-4-[(4-chlorophenyl)-propan-2-ylphosphoryl]benzene Chemical compound C=1C=C(Cl)C=CC=1P(=O)(C(C)C)C1=CC=C(Cl)C=C1 ZSKJUMNEBQQVDZ-UHFFFAOYSA-N 0.000 description 2
- 241000239290 Araneae Species 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- STUSTWKEFDQFFZ-UHFFFAOYSA-N Chlordimeform Chemical compound CN(C)C=NC1=CC=C(Cl)C=C1C STUSTWKEFDQFFZ-UHFFFAOYSA-N 0.000 description 2
- CDEMHJCJMMOFMB-UHFFFAOYSA-M ClC1=CC=C([Mg]Br)C=C1 Chemical compound ClC1=CC=C([Mg]Br)C=C1 CDEMHJCJMMOFMB-UHFFFAOYSA-M 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- 241001454295 Tetranychidae Species 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000005059 halophenyl group Chemical group 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- NHDODQWIKUYWMW-UHFFFAOYSA-N 1-bromo-4-chlorobenzene Chemical compound ClC1=CC=C(Br)C=C1 NHDODQWIKUYWMW-UHFFFAOYSA-N 0.000 description 1
- GJTBCPSGWCSGQP-UHFFFAOYSA-N 1-chloro-4-[(4-chloro-3-nitrophenyl)-methylphosphoryl]-2-nitrobenzene Chemical compound C=1C=C(Cl)C([N+]([O-])=O)=CC=1P(=O)(C)C1=CC=C(Cl)C([N+]([O-])=O)=C1 GJTBCPSGWCSGQP-UHFFFAOYSA-N 0.000 description 1
- KZEXHCYAEIYWBT-UHFFFAOYSA-N 3,3-bis(4-chlorophenyl)propylphosphane Chemical compound C=1C=C(Cl)C=CC=1C(CCP)C1=CC=C(Cl)C=C1 KZEXHCYAEIYWBT-UHFFFAOYSA-N 0.000 description 1
- IFFSWOWOJXOTEB-UHFFFAOYSA-N ClC1=CC=C(C=C1)P(CCC)C1=CC=C(C=C1)Cl.ClC1=CC=C(C=C1)P(CCC)(C1=CC=C(C=C1)Cl)=S Chemical compound ClC1=CC=C(C=C1)P(CCC)C1=CC=C(C=C1)Cl.ClC1=CC=C(C=C1)P(CCC)(C1=CC=C(C=C1)Cl)=S IFFSWOWOJXOTEB-UHFFFAOYSA-N 0.000 description 1
- BPRXSROCPYUAPA-UHFFFAOYSA-N ClC1=CC=C(C=C1)P(CCl)(C1=CC=C(C=C1)Cl)=O.ClC1=CC=C(C=C1)P(C)(C1=CC=C(C=C1)Cl)=O.ClC1=CC=C(C=C1)P(CC)C1=CC=C(C=C1)Cl.ClC1=CC=C(C=C1)P(CC)(C1=CC=C(C=C1)Cl)=O Chemical compound ClC1=CC=C(C=C1)P(CCl)(C1=CC=C(C=C1)Cl)=O.ClC1=CC=C(C=C1)P(C)(C1=CC=C(C=C1)Cl)=O.ClC1=CC=C(C=C1)P(CC)C1=CC=C(C=C1)Cl.ClC1=CC=C(C=C1)P(CC)(C1=CC=C(C=C1)Cl)=O BPRXSROCPYUAPA-UHFFFAOYSA-N 0.000 description 1
- DKJIXZDUYGOLDB-UHFFFAOYSA-N FC1=CC=C(C=C1)P(C)(C1=CC=C(C=C1)F)=O.BrC1=CC=C(C=C1)P(C)(C1=CC=C(C=C1)Br)=O.C(C)(C)(C)[PH2]=O Chemical compound FC1=CC=C(C=C1)P(C)(C1=CC=C(C=C1)F)=O.BrC1=CC=C(C=C1)P(C)(C1=CC=C(C=C1)Br)=O.C(C)(C)(C)[PH2]=O DKJIXZDUYGOLDB-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241000158728 Meliaceae Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 241000819999 Nymphes Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Chemical class 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241001454293 Tetranychus urticae Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229960000892 attapulgite Drugs 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
- VMRAJYCJJIKSGU-UHFFFAOYSA-N bis(4-chlorophenyl)-propyl-sulfanylidene-$l^{5}-phosphane Chemical compound C=1C=C(Cl)C=CC=1P(=S)(CCC)C1=CC=C(Cl)C=C1 VMRAJYCJJIKSGU-UHFFFAOYSA-N 0.000 description 1
- VPMOHHDYPLTCHG-UHFFFAOYSA-N bis(4-chlorophenyl)methylphosphane Chemical compound C=1C=C(Cl)C=CC=1C(P)C1=CC=C(Cl)C=C1 VPMOHHDYPLTCHG-UHFFFAOYSA-N 0.000 description 1
- 230000001925 catabolic effect Effects 0.000 description 1
- STUSTWKEFDQFFZ-KPKJPENVSA-N chlordimeform Chemical compound CN(C)\C=N\C1=CC=C(Cl)C=C1C STUSTWKEFDQFFZ-KPKJPENVSA-N 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- CDPKWOKGVUHZFR-UHFFFAOYSA-N dichloro(methyl)phosphane Chemical compound CP(Cl)Cl CDPKWOKGVUHZFR-UHFFFAOYSA-N 0.000 description 1
- PVTHAGJZMANMRT-UHFFFAOYSA-N dichloro(propyl)phosphane Chemical compound CCCP(Cl)Cl PVTHAGJZMANMRT-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 239000011872 intimate mixture Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 235000014666 liquid concentrate Nutrition 0.000 description 1
- BCDIWLCKOCHCIH-UHFFFAOYSA-N methylphosphinic acid Chemical compound CP(O)=O BCDIWLCKOCHCIH-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 231100000194 ovacidal Toxicity 0.000 description 1
- 230000003151 ovacidal effect Effects 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 238000003359 percent control normalization Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 239000011505 plaster Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000004659 sterilization and disinfection Methods 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
- HECARDHTAYKBAZ-UHFFFAOYSA-N tert-butyl(oxido)phosphanium Chemical compound CC(C)(C)[PH2]=O HECARDHTAYKBAZ-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
- C07F9/5325—Aromatic phosphine oxides or thioxides (P-C aromatic linkage)
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
- A01N57/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing aromatic radicals
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Dentistry (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/729,029 US4101655A (en) | 1975-03-06 | 1976-10-04 | Insecticidal and ovicidal method |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH627620A5 true CH627620A5 (en) | 1982-01-29 |
Family
ID=24929286
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1210277A CH627620A5 (en) | 1976-10-04 | 1977-10-04 | Method and composition for controlling insects and acarids |
Country Status (12)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3425282A1 (de) * | 1984-07-10 | 1986-01-16 | Röhm GmbH, 6100 Darmstadt | Verfahren zur herstellung aromatischer phosphorverbindungen |
| DE3426722A1 (de) * | 1984-07-20 | 1986-01-23 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung bifunktioneller tertiaerer aromatischer phosphansulfide |
| DE3601247A1 (de) * | 1986-01-17 | 1987-07-23 | Hoechst Ag | Verfahren zur herstellung bifunktioneller tertiaerer aromatischer phosphansulfide sowie einige spezielle vertreter dieser verbindungsklasse |
| JP2004182704A (ja) * | 2002-12-06 | 2004-07-02 | S T Chem Co Ltd | 穀物・乾物用防虫剤及び穀物・乾物害虫の防虫方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3989824A (en) * | 1975-03-06 | 1976-11-02 | M & T Chemicals Inc. | Method for controlling acarids with phosphine oxides |
-
1977
- 1977-09-02 GB GB36817/77A patent/GB1561198A/en not_active Expired
- 1977-09-02 IL IL52889A patent/IL52889A0/xx unknown
- 1977-09-27 CA CA287,639A patent/CA1084837A/en not_active Expired
- 1977-09-27 NL NL7710537A patent/NL7710537A/xx not_active Application Discontinuation
- 1977-09-29 DE DE19772743848 patent/DE2743848A1/de not_active Withdrawn
- 1977-09-30 JP JP11697577A patent/JPS5344631A/ja active Granted
- 1977-10-01 ES ES462836A patent/ES462836A1/es not_active Expired
- 1977-10-03 IT IT09587/77A patent/IT1090775B/it active
- 1977-10-04 CH CH1210277A patent/CH627620A5/de not_active IP Right Cessation
- 1977-10-04 FR FR7729754A patent/FR2366301A1/fr active Granted
- 1977-10-04 AU AU29324/77A patent/AU507044B2/en not_active Expired
- 1977-10-04 ZA ZA00775930A patent/ZA775930B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ZA775930B (en) | 1978-05-30 |
| NL7710537A (nl) | 1978-04-06 |
| IL52889A0 (en) | 1977-11-30 |
| JPS5344631A (en) | 1978-04-21 |
| CA1084837A (en) | 1980-09-02 |
| DE2743848A1 (de) | 1978-04-06 |
| GB1561198A (en) | 1980-02-13 |
| IT1090775B (it) | 1985-06-26 |
| ES462836A1 (es) | 1978-12-01 |
| AU2932477A (en) | 1979-05-24 |
| FR2366301B1 (enrdf_load_stackoverflow) | 1984-04-27 |
| AU507044B2 (en) | 1980-01-31 |
| FR2366301A1 (fr) | 1978-04-28 |
| JPS6210202B2 (enrdf_load_stackoverflow) | 1987-03-05 |
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| PL | Patent ceased | ||
| PL | Patent ceased |