DEG0017346MA - - Google Patents
Info
- Publication number
- DEG0017346MA DEG0017346MA DEG0017346MA DE G0017346M A DEG0017346M A DE G0017346MA DE G0017346M A DEG0017346M A DE G0017346MA
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- ester
- acid
- thiolthionophosphoric
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 239000002253 acid Substances 0.000 claims description 15
- 150000002148 esters Chemical class 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 150000001447 alkali salts Chemical class 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims 1
- 125000004970 halomethyl group Chemical group 0.000 claims 1
- -1 o-diisopropyl-S-phenyl-mercaptomethyl ester Chemical class 0.000 description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000000895 acaricidal effect Effects 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- KVLNFTDTHDZRGU-UHFFFAOYSA-N 1,2-dichloro-4-(chloromethylsulfanyl)benzene Chemical compound ClCSC1=CC=C(Cl)C(Cl)=C1 KVLNFTDTHDZRGU-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- 238000000199 molecular distillation Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- LVWBJSVJGDVOSC-UHFFFAOYSA-N 1,2,4-trichloro-5-[chloro-[chloro-(2,4,5-trichlorophenyl)methyl]sulfanylmethyl]benzene Chemical compound ClC1=C(C=C(C(=C1)Cl)Cl)C(Cl)SC(C1=C(C=C(C(=C1)Cl)Cl)Cl)Cl LVWBJSVJGDVOSC-UHFFFAOYSA-N 0.000 description 1
- KILGRDQUAUJEOX-UHFFFAOYSA-N 1,2-dichloro-4-[chloro-[chloro-(3,4-dichlorophenyl)methyl]sulfanylmethyl]benzene Chemical compound ClC=1C=C(C=CC1Cl)C(Cl)SC(C1=CC(=C(C=C1)Cl)Cl)Cl KILGRDQUAUJEOX-UHFFFAOYSA-N 0.000 description 1
- JPFKCGVGTFHSML-UHFFFAOYSA-N 1,4-dichloro-2-[chloro-[chloro-(2,5-dichlorophenyl)methyl]sulfanylmethyl]benzene Chemical compound ClC1=C(C=C(C=C1)Cl)C(Cl)SC(C1=C(C=CC(=C1)Cl)Cl)Cl JPFKCGVGTFHSML-UHFFFAOYSA-N 0.000 description 1
- RTKGBOLTBOTURK-UHFFFAOYSA-N 1-(chloromethylsulfanyl)-4-fluorobenzene Chemical compound FC1=CC=C(SCCl)C=C1 RTKGBOLTBOTURK-UHFFFAOYSA-N 0.000 description 1
- GEOWMGXEZOADNA-UHFFFAOYSA-N 1-(chloromethylsulfanyl)-4-methoxybenzene Chemical compound COC1=CC=C(SCCl)C=C1 GEOWMGXEZOADNA-UHFFFAOYSA-N 0.000 description 1
- IWLRNOWIBGYXKM-UHFFFAOYSA-N 1-chloro-4-[chloro-[chloro-(4-chlorophenyl)methyl]sulfanylmethyl]benzene Chemical compound ClC1=CC=C(C=C1)C(Cl)SC(C1=CC=C(C=C1)Cl)Cl IWLRNOWIBGYXKM-UHFFFAOYSA-N 0.000 description 1
- SHBIPXMJAAVLGL-UHFFFAOYSA-N 2,4-dichloro-5-methylbenzenethiol Chemical compound CC1=CC(S)=C(Cl)C=C1Cl SHBIPXMJAAVLGL-UHFFFAOYSA-N 0.000 description 1
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 1
- HNJZDPKMMZXSKT-UHFFFAOYSA-N 3,4-dichlorobenzenethiol Chemical compound SC1=CC=C(Cl)C(Cl)=C1 HNJZDPKMMZXSKT-UHFFFAOYSA-N 0.000 description 1
- MTKAJLNGIVXZIS-UHFFFAOYSA-N 3,4-dimethoxybenzenethiol Chemical compound COC1=CC=C(S)C=C1OC MTKAJLNGIVXZIS-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- OKIHXNKYYGUVTE-UHFFFAOYSA-N 4-Fluorothiophenol Chemical compound FC1=CC=C(S)C=C1 OKIHXNKYYGUVTE-UHFFFAOYSA-N 0.000 description 1
- FTBCOQFMQSTCQQ-UHFFFAOYSA-N 4-bromobenzenethiol Chemical compound SC1=CC=C(Br)C=C1 FTBCOQFMQSTCQQ-UHFFFAOYSA-N 0.000 description 1
- 241000239290 Araneae Species 0.000 description 1
- YVGGHNCTFXOJCH-UHFFFAOYSA-N DDT Chemical compound C1=CC(Cl)=CC=C1C(C(Cl)(Cl)Cl)C1=CC=C(Cl)C=C1 YVGGHNCTFXOJCH-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 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
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 241001454293 Tetranychus urticae Species 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- HUGPKRHWFXCKPA-UHFFFAOYSA-N [chloro-[chloro(phenyl)methyl]sulfanylmethyl]benzene Chemical compound C=1C=CC=CC=1C(Cl)SC(Cl)C1=CC=CC=C1 HUGPKRHWFXCKPA-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- KRIFIIWBVJKVST-UHFFFAOYSA-N chloro(chloromethylsulfanyl)methane Chemical compound ClCSCCl KRIFIIWBVJKVST-UHFFFAOYSA-N 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical class OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 230000009885 systemic effect Effects 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
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Family
ID=
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