NL8006159A - Esters van heterocyclische alcoholen, werkwijze voor hun bereiding en pesticide-samenstellingen, die deze verbindingen bevatten. - Google Patents
Esters van heterocyclische alcoholen, werkwijze voor hun bereiding en pesticide-samenstellingen, die deze verbindingen bevatten. Download PDFInfo
- Publication number
- NL8006159A NL8006159A NL8006159A NL8006159A NL8006159A NL 8006159 A NL8006159 A NL 8006159A NL 8006159 A NL8006159 A NL 8006159A NL 8006159 A NL8006159 A NL 8006159A NL 8006159 A NL8006159 A NL 8006159A
- Authority
- NL
- Netherlands
- Prior art keywords
- cyano
- formula
- dimethyl
- cyclopropane
- phenoxy
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 61
- 239000000203 mixture Substances 0.000 title claims description 26
- 238000002360 preparation method Methods 0.000 title claims description 24
- 238000000034 method Methods 0.000 title claims description 23
- 150000001298 alcohols Chemical class 0.000 title description 2
- 239000000575 pesticide Substances 0.000 title description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 58
- -1 (S) o-cyano 6-phenoxy 2-pyridylmethyl ester Chemical class 0.000 claims description 37
- 125000004432 carbon atom Chemical group C* 0.000 claims description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 34
- CYCYDSJDZNVSPP-ZZKAVYKESA-N (1s,3s)-3-(1,2-dibromo-2,2-dichloroethyl)-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)[C@@H](C(Br)C(Cl)(Cl)Br)[C@@H]1C(O)=O CYCYDSJDZNVSPP-ZZKAVYKESA-N 0.000 claims description 33
- 150000002148 esters Chemical class 0.000 claims description 33
- 239000001257 hydrogen Substances 0.000 claims description 32
- 239000002253 acid Substances 0.000 claims description 27
- 229910052799 carbon Inorganic materials 0.000 claims description 22
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 claims description 21
- 239000000460 chlorine Substances 0.000 claims description 19
- 125000001424 substituent group Chemical group 0.000 claims description 17
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 16
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
- 229910052801 chlorine Inorganic materials 0.000 claims description 14
- 239000004480 active ingredient Substances 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- VSBCUTLTLUSECJ-ZZKAVYKESA-N (1s,3s)-2,2-dimethyl-3-(1,2,2,2-tetrabromoethyl)cyclopropane-1-carboxylic acid Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@@H]1C(O)=O VSBCUTLTLUSECJ-ZZKAVYKESA-N 0.000 claims description 9
- CYCYDSJDZNVSPP-UHFFFAOYSA-N 3-(1,2-dibromo-2,2-dichloroethyl)-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)C(C(Br)C(Cl)(Cl)Br)C1C(O)=O CYCYDSJDZNVSPP-UHFFFAOYSA-N 0.000 claims description 9
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 230000000895 acaricidal effect Effects 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- VSBCUTLTLUSECJ-UHFFFAOYSA-N 2,2-dimethyl-3-(1,2,2,2-tetrabromoethyl)cyclopropane-1-carboxylic acid Chemical compound CC1(C)C(C(Br)C(Br)(Br)Br)C1C(O)=O VSBCUTLTLUSECJ-UHFFFAOYSA-N 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 claims description 4
- 230000000855 fungicidal effect Effects 0.000 claims description 4
- 239000005645 nematicide Substances 0.000 claims description 4
- 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 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 239000002917 insecticide Substances 0.000 claims description 3
- CFHSUPQCJIHGEG-UHFFFAOYSA-N 2-(1,2-dibromo-2,2-dichloroethyl)cyclopropane-1-carboxylic acid Chemical compound BrC(C(Cl)(Cl)Br)C1CC1C(=O)O CFHSUPQCJIHGEG-UHFFFAOYSA-N 0.000 claims description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- 239000012736 aqueous medium Substances 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
- 230000002140 halogenating effect Effects 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 238000012546 transfer Methods 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- GLFDLEXFOHUASB-UHFFFAOYSA-N trimethyl(tetradecyl)azanium Chemical group CCCCCCCCCCCCCC[N+](C)(C)C GLFDLEXFOHUASB-UHFFFAOYSA-N 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 36
- 229940126062 Compound A Drugs 0.000 description 19
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 19
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 14
- LLMLSUSAKZVFOA-UJURSFKZSA-N (1S,3R)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@@H]1C(O)=O LLMLSUSAKZVFOA-UJURSFKZSA-N 0.000 description 13
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 13
- 125000004076 pyridyl group Chemical group 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- 238000004587 chromatography analysis Methods 0.000 description 12
- 230000000749 insecticidal effect Effects 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 241000238631 Hexapoda Species 0.000 description 10
- LLMLSUSAKZVFOA-UHFFFAOYSA-N 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(O)=O LLMLSUSAKZVFOA-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 241000257226 Muscidae Species 0.000 description 7
- 150000007513 acids Chemical class 0.000 description 7
- 238000011835 investigation Methods 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 230000009102 absorption Effects 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- 241000238876 Acari Species 0.000 description 5
- 125000003158 alcohol group Chemical group 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 239000003480 eluent Substances 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 241000256250 Spodoptera littoralis Species 0.000 description 4
- 230000031709 bromination Effects 0.000 description 4
- 238000005893 bromination reaction Methods 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- YZFJCORZVYKNLY-UHFFFAOYSA-N 6-phenoxypyridine-2-carbaldehyde Chemical compound O=CC1=CC=CC(OC=2C=CC=CC=2)=N1 YZFJCORZVYKNLY-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 241000238657 Blattella germanica Species 0.000 description 3
- CXRFDZFCGOPDTD-UHFFFAOYSA-M Cetrimide Chemical compound [Br-].CCCCCCCCCCCCCC[N+](C)(C)C CXRFDZFCGOPDTD-UHFFFAOYSA-M 0.000 description 3
- 241001301805 Epilachna Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 230000000699 topical effect Effects 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- 241000255925 Diptera Species 0.000 description 2
- 244000046052 Phaseolus vulgaris Species 0.000 description 2
- 241001454293 Tetranychus urticae Species 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 210000000038 chest Anatomy 0.000 description 2
- 238000013375 chromatographic separation Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000004495 emulsifiable concentrate Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000003197 gene knockdown Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 239000008240 homogeneous mixture Substances 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000000361 pesticidal effect Effects 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
- 229920000053 polysorbate 80 Polymers 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- PTWUJNIBSWMQFA-ZZKAVYKESA-N (1S,3S)-3-(1,2-dibromo-2,2-dichloroethyl)-2,2-dimethylcyclopropane-1-carbonyl chloride Chemical compound CC1([C@H]([C@@H]1C(C(Cl)(Cl)Br)Br)C(=O)Cl)C PTWUJNIBSWMQFA-ZZKAVYKESA-N 0.000 description 1
- HJOZIISUXJHSEK-UHFFFAOYSA-N 1-(1,2,2,2-tetrabromoethyl)cyclopropane-1-carboxylic acid Chemical compound BrC(Br)(Br)C(Br)C1(C(=O)O)CC1 HJOZIISUXJHSEK-UHFFFAOYSA-N 0.000 description 1
- QMGHQPCOAPMJTH-UHFFFAOYSA-N 1-(1,2-dibromo-2,2-dichloroethyl)cyclopropane-1-carboxylic acid Chemical compound ClC(Br)(Cl)C(Br)C1(C(=O)O)CC1 QMGHQPCOAPMJTH-UHFFFAOYSA-N 0.000 description 1
- OJSSLUADXGVPCE-UHFFFAOYSA-N 2,2-dimethyl-3-(1,2,2,2-tetrabromoethyl)cyclopropane-1-carbonyl chloride Chemical compound CC1(C)C(C(Br)C(Br)(Br)Br)C1C(Cl)=O OJSSLUADXGVPCE-UHFFFAOYSA-N 0.000 description 1
- NUQSJBAQSZZDJA-UHFFFAOYSA-N 2,2-dimethyl-3-(1,2,2,2-tetrachloroethyl)cyclopropane-1-carboxylic acid Chemical class CC1(C)C(C(Cl)C(Cl)(Cl)Cl)C1C(O)=O NUQSJBAQSZZDJA-UHFFFAOYSA-N 0.000 description 1
- IGPWJPATVJVGAI-UHFFFAOYSA-N 2-(1,2,2,2-tetrabromoethyl)cyclopropane-1-carboxylic acid Chemical compound OC(=O)C1CC1C(Br)C(Br)(Br)Br IGPWJPATVJVGAI-UHFFFAOYSA-N 0.000 description 1
- ZSLSWXUSULSWQT-UHFFFAOYSA-N 3-(1,2-dibromo-2,2-difluoroethyl)-2,2-dimethylcyclopropane-1-carboxylic acid Chemical class CC1(C)C(C(Br)C(F)(F)Br)C1C(O)=O ZSLSWXUSULSWQT-UHFFFAOYSA-N 0.000 description 1
- GBGFOSFSXCKFED-UHFFFAOYSA-N 3-(1,2-dibromo-2-chloro-2-fluoroethyl)-2,2-dimethylcyclopropane-1-carboxylic acid Chemical class CC1(C)C(C(Br)C(F)(Cl)Br)C1C(O)=O GBGFOSFSXCKFED-UHFFFAOYSA-N 0.000 description 1
- XOMUIESIEFTOBQ-UHFFFAOYSA-N 3-(1,2-dibromo-2-chloroethyl)-2,2-dimethylcyclopropane-1-carboxylic acid Chemical class CC1(C)C(C(Br)C(Cl)Br)C1C(O)=O XOMUIESIEFTOBQ-UHFFFAOYSA-N 0.000 description 1
- CHLAOFANYRDCPD-UHFFFAOYSA-N 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carbonyl chloride Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(Cl)=O CHLAOFANYRDCPD-UHFFFAOYSA-N 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- 241001600407 Aphis <genus> Species 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 1
- 241000254173 Coleoptera Species 0.000 description 1
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical group C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000255777 Lepidoptera Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000256248 Spodoptera Species 0.000 description 1
- 240000004460 Tanacetum coccineum Species 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 244000000054 animal parasite Species 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- BFAKENXZKHGIGE-UHFFFAOYSA-N bis(2,3,5,6-tetrafluoro-4-iodophenyl)diazene Chemical compound FC1=C(C(=C(C(=C1F)I)F)F)N=NC1=C(C(=C(C(=C1F)F)I)F)F BFAKENXZKHGIGE-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- ZOOSILUVXHVRJE-UHFFFAOYSA-N cyclopropanecarbonyl chloride Chemical compound ClC(=O)C1CC1 ZOOSILUVXHVRJE-UHFFFAOYSA-N 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 230000001418 larval effect Effects 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
- C07D213/647—One oxygen atom attached in position 2 or 6 and having in the molecule an acyl radical containing a saturated three-membered ring, e.g. chrysanthemumic acid esters
-
- 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
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7928049A FR2469403A1 (fr) | 1979-11-14 | 1979-11-14 | Esters d'alcools heterocycliques, leurs procedes de preparation et les compositions les renfermant |
| FR7928049 | 1979-11-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8006159A true NL8006159A (nl) | 1981-06-16 |
Family
ID=9231659
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8006159A NL8006159A (nl) | 1979-11-14 | 1980-11-11 | Esters van heterocyclische alcoholen, werkwijze voor hun bereiding en pesticide-samenstellingen, die deze verbindingen bevatten. |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4315012A (cg-RX-API-DMAC7.html) |
| JP (1) | JPS5692867A (cg-RX-API-DMAC7.html) |
| BR (1) | BR8007300A (cg-RX-API-DMAC7.html) |
| CH (1) | CH649534A5 (cg-RX-API-DMAC7.html) |
| DE (1) | DE3043109A1 (cg-RX-API-DMAC7.html) |
| EG (1) | EG14900A (cg-RX-API-DMAC7.html) |
| FR (1) | FR2469403A1 (cg-RX-API-DMAC7.html) |
| GB (1) | GB2063878B (cg-RX-API-DMAC7.html) |
| IT (1) | IT1146998B (cg-RX-API-DMAC7.html) |
| NL (1) | NL8006159A (cg-RX-API-DMAC7.html) |
| OA (1) | OA06635A (cg-RX-API-DMAC7.html) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2486078A1 (fr) * | 1980-07-04 | 1982-01-08 | Roussel Uclaf | Nouveaux esters de l'acide cyclopropane carboxylique, leur procede de preparation et leur application a la lutte contre les parasites |
| US4546189A (en) * | 1980-10-23 | 1985-10-08 | The Dow Chemical Company | Preparation of cyano(6-(substituted phenoxy)-2-pyridinyl)methyl esters of 3-(2,2-dihaloethenyl)-2,2-dimethylcyclopropane carboxylic acids |
| JPS5835175A (ja) * | 1981-08-25 | 1983-03-01 | Nissan Chem Ind Ltd | 新規カルボン酸エステルおよびこれらを含有する殺虫殺ダニ剤 |
| US6881838B2 (en) * | 2002-05-21 | 2005-04-19 | A.E. Staley Manufacturing Company | Polysaccharide gum and process for its manufacture |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3711486A (en) * | 1969-03-17 | 1973-01-16 | Dow Chemical Co | Substituted(trifluoromethyl)pyridines |
| FR2398041A2 (fr) * | 1977-07-19 | 1979-02-16 | Roussel Uclaf | Esters d'acides cyclopropane carboxylique comportant un substituant polyhalogene, procede de preparation et leur application comme insecticides, acaricides, nematicides et comme medicaments veterinaires |
| TR20113A (tr) * | 1977-02-11 | 1980-08-07 | Ciba Geigy Ag | Yeni esterler |
| DE2805274A1 (de) * | 1977-02-11 | 1978-08-17 | Ciba Geigy Ag | Cyclopropankarbonsaeureester, verfahren zu ihrer herstellung und ihre verwendung in der schaedlingsbekaempfung |
| TR20011A (tr) * | 1977-02-11 | 1980-06-16 | Ciba Geigy Ag | Yeni esterler |
| US4163787A (en) * | 1977-03-14 | 1979-08-07 | The Dow Chemical Company | Substituted pyridine methyl esters of cyclopropane carboxylic acids and their use as insecticides |
| DE2829329A1 (de) * | 1977-07-05 | 1979-01-25 | Ciba Geigy Ag | Cyclopropankarbonsaeureester und ihre salze mit anorganischen und organischen saeuren, verfahren zu ihrer herstellung und ihre verwendung in der schaedlingsbekaempfung |
| FR2398714A1 (fr) * | 1977-07-25 | 1979-02-23 | Roussel Uclaf | Nouveaux acides cyclopropane carboxyliques comportant un substituant polyhalogene et procede de preparation |
| JPS5822149B2 (ja) * | 1979-04-04 | 1983-05-06 | 住友化学工業株式会社 | 新規カルボン酸エステル、その製造法およびそれを有効成分とする殺虫、殺ダニ剤 |
| US4221799A (en) * | 1979-07-30 | 1980-09-09 | The Dow Chemical | Substituted pyridine methyl esters of tetramethyl cyclopropane carboxylic acids and their use as insecticides |
| US4238614A (en) * | 1979-08-30 | 1980-12-09 | Zoecon Corporation | Pyridyl esters of ether and thioether substituted cyclopropanecarboxylic acids |
| US4248875A (en) * | 1979-08-31 | 1981-02-03 | Zoecon Corporation | Pyridyl esters and thiolesters of α-substituted unsaturated acids |
-
1979
- 1979-11-14 FR FR7928049A patent/FR2469403A1/fr active Granted
-
1980
- 1980-10-06 OA OA57229A patent/OA06635A/xx unknown
- 1980-11-10 BR BR8007300A patent/BR8007300A/pt unknown
- 1980-11-10 US US06/205,245 patent/US4315012A/en not_active Expired - Lifetime
- 1980-11-11 NL NL8006159A patent/NL8006159A/nl not_active Application Discontinuation
- 1980-11-13 IT IT50157/80A patent/IT1146998B/it active
- 1980-11-13 GB GB8036447A patent/GB2063878B/en not_active Expired
- 1980-11-13 CH CH8431/80A patent/CH649534A5/fr not_active IP Right Cessation
- 1980-11-13 JP JP15893580A patent/JPS5692867A/ja active Pending
- 1980-11-14 DE DE19803043109 patent/DE3043109A1/de not_active Withdrawn
- 1980-11-15 EG EG709/80A patent/EG14900A/xx active
Also Published As
| Publication number | Publication date |
|---|---|
| CH649534A5 (fr) | 1985-05-31 |
| JPS5692867A (en) | 1981-07-27 |
| IT8050157A0 (it) | 1980-11-13 |
| BR8007300A (pt) | 1981-05-19 |
| OA06635A (fr) | 1981-08-31 |
| DE3043109A1 (de) | 1981-08-27 |
| FR2469403B1 (cg-RX-API-DMAC7.html) | 1983-02-18 |
| GB2063878B (en) | 1983-06-29 |
| EG14900A (en) | 1985-06-30 |
| IT1146998B (it) | 1986-11-19 |
| US4315012A (en) | 1982-02-09 |
| GB2063878A (en) | 1981-06-10 |
| FR2469403A1 (fr) | 1981-05-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A85 | Still pending on 85-01-01 | ||
| BA | A request for search or an international-type search has been filed | ||
| BB | A search report has been drawn up | ||
| BC | A request for examination has been filed | ||
| BV | The patent application has lapsed |