DE2118776A1 - - Google Patents
Info
- Publication number
- DE2118776A1 DE2118776A1 DE19712118776 DE2118776A DE2118776A1 DE 2118776 A1 DE2118776 A1 DE 2118776A1 DE 19712118776 DE19712118776 DE 19712118776 DE 2118776 A DE2118776 A DE 2118776A DE 2118776 A1 DE2118776 A1 DE 2118776A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- acetic acid
- halogen
- diphenyl
- acid alkyl
- 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.)
- Pending
Links
- -1 benzilic acid ester Chemical class 0.000 claims description 13
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 241000238876 Acari Species 0.000 claims description 8
- 230000000895 acaricidal effect Effects 0.000 claims description 8
- 230000002140 halogenating effect Effects 0.000 claims description 7
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 6
- 229910052698 phosphorus Inorganic materials 0.000 claims description 6
- 239000011574 phosphorus Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 239000004606 Fillers/Extenders Substances 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 229940087675 benzilic acid Drugs 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 description 15
- 239000002904 solvent Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 239000003995 emulsifying agent Substances 0.000 description 5
- 230000032050 esterification Effects 0.000 description 5
- 238000005886 esterification reaction Methods 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 244000046052 Phaseolus vulgaris Species 0.000 description 4
- 241001454295 Tetranychidae Species 0.000 description 4
- 241001454293 Tetranychus urticae Species 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000004342 Benzoyl peroxide Substances 0.000 description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 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
- 235000019400 benzoyl peroxide Nutrition 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- KGYNKXFCPICMMI-UHFFFAOYSA-N methyl 2,2-bis(4-chlorophenyl)-2-hydroxyacetate Chemical compound C=1C=C(Cl)C=CC=1C(O)(C(=O)OC)C1=CC=C(Cl)C=C1 KGYNKXFCPICMMI-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 241000488583 Panonychus ulmi Species 0.000 description 2
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 2
- 241001396980 Phytonemus pallidus Species 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 241001454294 Tetranychus Species 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 235000013312 flour Nutrition 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 229920000151 polyglycol Polymers 0.000 description 2
- 239000010695 polyglycol Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- YPWDDFGPYBIPBG-UHFFFAOYSA-N 1-bromo-4-[1-(4-bromophenyl)-2,2,2-trichloroethyl]benzene Chemical compound C=1C=C(Br)C=CC=1C(C(Cl)(Cl)Cl)C1=CC=C(Br)C=C1 YPWDDFGPYBIPBG-UHFFFAOYSA-N 0.000 description 1
- CLSXNIPAOWPLFR-UHFFFAOYSA-N 1-fluoro-4-[2,2,2-trichloro-1-(4-fluorophenyl)ethyl]benzene Chemical compound C1=CC(F)=CC=C1C(C(Cl)(Cl)Cl)C1=CC=C(F)C=C1 CLSXNIPAOWPLFR-UHFFFAOYSA-N 0.000 description 1
- HSQGVJITZXIFPO-UHFFFAOYSA-N 2,2-bis(4-fluorophenyl)propanoic acid Chemical compound C=1C=C(F)C=CC=1C(C(O)=O)(C)C1=CC=C(F)C=C1 HSQGVJITZXIFPO-UHFFFAOYSA-N 0.000 description 1
- LXFMMUDXRIMBHN-UHFFFAOYSA-N 4,4'-dichlorobenzilic acid Chemical class C=1C=C(Cl)C=CC=1C(O)(C(=O)O)C1=CC=C(Cl)C=C1 LXFMMUDXRIMBHN-UHFFFAOYSA-N 0.000 description 1
- KNIUHBNRWZGIQQ-UHFFFAOYSA-N 7-diethoxyphosphinothioyloxy-4-methylchromen-2-one Chemical compound CC1=CC(=O)OC2=CC(OP(=S)(OCC)OCC)=CC=C21 KNIUHBNRWZGIQQ-UHFFFAOYSA-N 0.000 description 1
- 241000489242 Amphitetranychus viennensis Species 0.000 description 1
- 241001221118 Cecidophyopsis ribis Species 0.000 description 1
- 241001221110 Eriophyidae Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241000088861 Latua Species 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241001459558 Monographella nivalis Species 0.000 description 1
- 241000238887 Ornithodoros Species 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 241001361634 Rhizoctonia Species 0.000 description 1
- 241001065719 Tetranychus ludeni Species 0.000 description 1
- 241000865903 Thielaviopsis Species 0.000 description 1
- 241000722093 Tilletia caries Species 0.000 description 1
- 241000514371 Ustilago avenae Species 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 125000006177 alkyl benzyl group Chemical group 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- UKXSKSHDVLQNKG-UHFFFAOYSA-N benzilic acid Chemical class C=1C=CC=CC=1C(O)(C(=O)O)C1=CC=CC=C1 UKXSKSHDVLQNKG-UHFFFAOYSA-N 0.000 description 1
- 238000006833 benzilic acid rearrangement reaction Methods 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 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
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- NNGLRANSPULJCT-UHFFFAOYSA-N methyl 2,2-bis(4-fluorophenyl)acetate Chemical compound C=1C=C(F)C=CC=1C(C(=O)OC)C1=CC=C(F)C=C1 NNGLRANSPULJCT-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010992 reflux Methods 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
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/62—Halogen-containing esters
- C07C69/63—Halogen-containing esters of saturated acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19712118776 DE2118776A1 (enrdf_load_stackoverflow) | 1971-04-17 | 1971-04-17 | |
NL7205091A NL7205091A (enrdf_load_stackoverflow) | 1971-04-17 | 1972-04-14 | |
IL39220A IL39220A0 (en) | 1971-04-17 | 1972-04-14 | Alpha-halo-alpha,alpha-diphenyl-acetic acid alkyl esters,processes for their preparation,and their use as acaricides |
ZA722523A ZA722523B (en) | 1971-04-17 | 1972-04-14 | Alpha-halo-alpha,alpha-diphenyl-acetic acid alkyl esters,processes for their preparation and their use as acaricides |
BR2246/72A BR7202246D0 (pt) | 1971-04-17 | 1972-04-14 | Processo para a preparacao ester alquilico de acido alfa-halogeneo-alfa, alfa-difenil-acetico e composicoes acaricidas a base deste |
BE782206A BE782206A (fr) | 1971-04-17 | 1972-04-17 | Nouveaux esters alkyliques d'acides alpha-halogeno-alpha, alpha-diphenyl-acetiques, leur procede de preparation et leur application comme acaricides |
FR7213404A FR2133813A1 (en) | 1971-04-17 | 1972-04-17 | Alpha-halo-alpha,alpha-diphenylacetic acid alkyl - esters - acaricides |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19712118776 DE2118776A1 (enrdf_load_stackoverflow) | 1971-04-17 | 1971-04-17 |
Publications (1)
Publication Number | Publication Date |
---|---|
DE2118776A1 true DE2118776A1 (enrdf_load_stackoverflow) | 1972-11-09 |
Family
ID=5805047
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19712118776 Pending DE2118776A1 (enrdf_load_stackoverflow) | 1971-04-17 | 1971-04-17 |
Country Status (7)
Country | Link |
---|---|
BE (1) | BE782206A (enrdf_load_stackoverflow) |
BR (1) | BR7202246D0 (enrdf_load_stackoverflow) |
DE (1) | DE2118776A1 (enrdf_load_stackoverflow) |
FR (1) | FR2133813A1 (enrdf_load_stackoverflow) |
IL (1) | IL39220A0 (enrdf_load_stackoverflow) |
NL (1) | NL7205091A (enrdf_load_stackoverflow) |
ZA (1) | ZA722523B (enrdf_load_stackoverflow) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1640359A3 (en) * | 1997-12-10 | 2006-04-05 | Nps Pharmaceuticals, Inc. | Anticonvulsant and central nervous system-active bis(fluorophenyl)alkylamides |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ES2341523B1 (es) * | 2008-12-18 | 2011-04-26 | Consejo Superior De Investigaciones Cientificas (Csic) | Haptenos, usos y metodo inmunoquimico para la deteccion de bromopropilato. |
-
1971
- 1971-04-17 DE DE19712118776 patent/DE2118776A1/de active Pending
-
1972
- 1972-04-14 IL IL39220A patent/IL39220A0/xx unknown
- 1972-04-14 BR BR2246/72A patent/BR7202246D0/pt unknown
- 1972-04-14 NL NL7205091A patent/NL7205091A/xx unknown
- 1972-04-14 ZA ZA722523A patent/ZA722523B/xx unknown
- 1972-04-17 FR FR7213404A patent/FR2133813A1/fr not_active Withdrawn
- 1972-04-17 BE BE782206A patent/BE782206A/xx unknown
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1640359A3 (en) * | 1997-12-10 | 2006-04-05 | Nps Pharmaceuticals, Inc. | Anticonvulsant and central nervous system-active bis(fluorophenyl)alkylamides |
Also Published As
Publication number | Publication date |
---|---|
BE782206A (fr) | 1972-10-17 |
BR7202246D0 (pt) | 1974-01-17 |
ZA722523B (en) | 1973-01-31 |
IL39220A0 (en) | 1972-06-28 |
FR2133813A1 (en) | 1972-12-01 |
NL7205091A (enrdf_load_stackoverflow) | 1972-10-19 |
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