HU189743B - Insecticide or acaricide compositions containing derivatives of /+/-substituted 2-indanole esters as active substances and process for preparing the active substances - Google Patents
Insecticide or acaricide compositions containing derivatives of /+/-substituted 2-indanole esters as active substances and process for preparing the active substances Download PDFInfo
- Publication number
- HU189743B HU189743B HU833138D HU313881D HU189743B HU 189743 B HU189743 B HU 189743B HU 833138 D HU833138 D HU 833138D HU 313881 D HU313881 D HU 313881D HU 189743 B HU189743 B HU 189743B
- Authority
- HU
- Hungary
- Prior art keywords
- cis
- phenyl
- formula
- alkyl
- substituted
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 62
- 230000000895 acaricidal effect Effects 0.000 title claims description 11
- 239000002917 insecticide Substances 0.000 title abstract description 10
- 150000002148 esters Chemical class 0.000 title description 15
- 239000000642 acaricide Substances 0.000 title description 4
- 238000004519 manufacturing process Methods 0.000 title description 4
- 239000013543 active substance Substances 0.000 title 2
- -1 phenoxy, phenylthio, benzyl Chemical group 0.000 claims abstract description 62
- 238000000034 method Methods 0.000 claims abstract description 40
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 19
- 239000001257 hydrogen Substances 0.000 claims abstract description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 8
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims abstract description 8
- 238000002360 preparation method Methods 0.000 claims description 40
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 27
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- 150000002367 halogens Chemical group 0.000 claims description 20
- 230000000749 insecticidal effect Effects 0.000 claims description 15
- 239000007787 solid Substances 0.000 claims description 15
- 239000004480 active ingredient Substances 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 239000004094 surface-active agent Substances 0.000 claims description 4
- 239000005995 Aluminium silicate Substances 0.000 claims description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 3
- 235000012211 aluminium silicate Nutrition 0.000 claims description 3
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 claims description 3
- 239000003350 kerosene Substances 0.000 claims description 3
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
- 239000011575 calcium Substances 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- 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 claims description 2
- 229910052901 montmorillonite Inorganic materials 0.000 claims description 2
- 239000000454 talc Substances 0.000 claims description 2
- 229910052623 talc Inorganic materials 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 3
- 239000003905 agrochemical Substances 0.000 claims 1
- KOQQTDQRCNDCLT-UHFFFAOYSA-N cyano benzenesulfonate Chemical compound C(#N)OS(=O)(=O)C1=CC=CC=C1 KOQQTDQRCNDCLT-UHFFFAOYSA-N 0.000 claims 1
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 45
- 150000001298 alcohols Chemical class 0.000 abstract description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 96
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 46
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 35
- 239000000243 solution Substances 0.000 description 33
- UPCFPYKJLSHYKD-UHFFFAOYSA-N 4-phenyl-2,3-dihydro-1h-inden-2-ol Chemical compound C=12CC(O)CC2=CC=CC=1C1=CC=CC=C1 UPCFPYKJLSHYKD-UHFFFAOYSA-N 0.000 description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- 239000003921 oil Substances 0.000 description 26
- 235000019198 oils Nutrition 0.000 description 26
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 230000002829 reductive effect Effects 0.000 description 24
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 23
- 239000011541 reaction mixture Substances 0.000 description 23
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 22
- 239000000047 product Substances 0.000 description 21
- 239000000460 chlorine Substances 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 239000002253 acid Substances 0.000 description 14
- 239000000706 filtrate Substances 0.000 description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- 230000000694 effects Effects 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000004458 analytical method Methods 0.000 description 12
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 12
- GRWFGVWFFZKLTI-UHFFFAOYSA-N rac-alpha-Pinene Natural products CC1=CCC2C(C)(C)C1C2 GRWFGVWFFZKLTI-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- YIAPLDFPUUJILH-UHFFFAOYSA-N indan-1-ol Chemical class C1=CC=C2C(O)CCC2=C1 YIAPLDFPUUJILH-UHFFFAOYSA-N 0.000 description 10
- KMGCKSAIIHOKCX-UHFFFAOYSA-N 2,3-dihydro-1h-inden-2-ol Chemical compound C1=CC=C2CC(O)CC2=C1 KMGCKSAIIHOKCX-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 241000238631 Hexapoda Species 0.000 description 8
- 239000000543 intermediate Substances 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 229930006718 (+)-alpha-pinene Natural products 0.000 description 7
- GRWFGVWFFZKLTI-RKDXNWHRSA-N (+)-α-pinene Chemical compound CC1=CC[C@H]2C(C)(C)[C@@H]1C2 GRWFGVWFFZKLTI-RKDXNWHRSA-N 0.000 description 7
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 7
- 125000003158 alcohol group Chemical group 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 7
- 238000006197 hydroboration reaction Methods 0.000 description 7
- 238000002329 infrared spectrum Methods 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- SPVZAYWHHVLPBN-UJURSFKZSA-N (1s,3r)-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)[C@@H](C=C(Cl)C(F)(F)F)[C@@H]1C(O)=O SPVZAYWHHVLPBN-UJURSFKZSA-N 0.000 description 6
- WOMLTCOPRFPVBR-UHFFFAOYSA-N 7-phenyl-1h-indene Chemical compound C=12CC=CC2=CC=CC=1C1=CC=CC=C1 WOMLTCOPRFPVBR-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 241000462639 Epilachna varivestis Species 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
- 239000007859 condensation product Substances 0.000 description 6
- 235000014113 dietary fatty acids Nutrition 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 239000000284 extract Substances 0.000 description 6
- 239000000194 fatty acid Substances 0.000 description 6
- 229930195729 fatty acid Natural products 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 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 5
- LLMLSUSAKZVFOA-INEUFUBQSA-N (1s,3s)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)[C@H](C=C(Cl)Cl)[C@@H]1C(O)=O LLMLSUSAKZVFOA-INEUFUBQSA-N 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- 241000196324 Embryophyta Species 0.000 description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical group OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 229910000085 borane Inorganic materials 0.000 description 5
- 230000018044 dehydration Effects 0.000 description 5
- 238000006297 dehydration reaction Methods 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000002728 pyrethroid Substances 0.000 description 5
- 239000000523 sample Substances 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- ABALMDTULZCSTP-INEUFUBQSA-N (1s,3r)-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropane-1-carbonyl chloride Chemical compound CC1(C)[C@H](C=C(Cl)C(F)(F)F)[C@@H]1C(Cl)=O ABALMDTULZCSTP-INEUFUBQSA-N 0.000 description 4
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 4
- UYSMIUXOZPFVJF-UHFFFAOYSA-N 4-phenyl-2,3-dihydro-1h-inden-1-ol Chemical compound OC1CCC2=C1C=CC=C2C1=CC=CC=C1 UYSMIUXOZPFVJF-UHFFFAOYSA-N 0.000 description 4
- 241000238876 Acari Species 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- 241000219843 Pisum Species 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 150000004702 methyl esters Chemical class 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000003579 shift reagent Substances 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 238000001179 sorption measurement Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- MDIQXIJPQWLFSD-INEUFUBQSA-N (1s,3s)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)[C@H](C=C(Br)Br)[C@@H]1C(O)=O MDIQXIJPQWLFSD-INEUFUBQSA-N 0.000 description 3
- RLRXIILIGUSQPE-MUVQZQTDSA-N (4-phenyl-2,3-dihydro-1h-inden-2-yl) (1s,3s)-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CC1(C)[C@H](C=C(Cl)C(F)(F)F)[C@@H]1C(=O)OC1CC2=C(C=3C=CC=CC=3)C=CC=C2C1 RLRXIILIGUSQPE-MUVQZQTDSA-N 0.000 description 3
- GRWFGVWFFZKLTI-IUCAKERBSA-N 1S,5S-(-)-alpha-Pinene Natural products CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 244000046052 Phaseolus vulgaris Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- MVNCAPSFBDBCGF-UHFFFAOYSA-N alpha-pinene Natural products CC1=CCC23C1CC2C3(C)C MVNCAPSFBDBCGF-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical class [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 3
- FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical compound BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 239000012259 ether extract Substances 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- VGLKHVQPWGFXEG-NCJHBDPTSA-K europium(3+);(1z)-2,2,3,3,4,4,4-heptafluoro-1-(4,7,7-trimethyl-3-oxo-2-bicyclo[2.2.1]heptanylidene)butan-1-olate Chemical compound [Eu+3].C1CC2(C)C(=O)\C(=C(/[O-])C(F)(F)C(F)(F)C(F)(F)F)C1C2(C)C.C1CC2(C)C(=O)\C(=C(/[O-])C(F)(F)C(F)(F)C(F)(F)F)C1C2(C)C.C1CC2(C)C(=O)\C(=C(/[O-])C(F)(F)C(F)(F)C(F)(F)F)C1C2(C)C VGLKHVQPWGFXEG-NCJHBDPTSA-K 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
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- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 2
- SFHVXKNMCGSLAR-UHFFFAOYSA-N 2,2,3,3-tetramethylcyclopropanecarboxylic acid Chemical compound CC1(C)C(C(O)=O)C1(C)C SFHVXKNMCGSLAR-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- 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 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
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- 241000238421 Arthropoda Species 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 241000254173 Coleoptera Species 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 241000258914 Oncopeltus Species 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 description 2
- UWTDFICHZKXYAC-UHFFFAOYSA-N boron;oxolane Chemical compound [B].C1CCOC1 UWTDFICHZKXYAC-UHFFFAOYSA-N 0.000 description 2
- 230000031709 bromination Effects 0.000 description 2
- 238000005893 bromination reaction Methods 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
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- 230000007935 neutral effect Effects 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- UYDLBVPAAFVANX-UHFFFAOYSA-N octylphenoxy polyethoxyethanol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(OCCOCCOCCOCCO)C=C1 UYDLBVPAAFVANX-UHFFFAOYSA-N 0.000 description 1
- 238000010915 one-step procedure Methods 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 229920001521 polyalkylene glycol ether Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- HYJYGLGUBUDSLJ-UHFFFAOYSA-N pyrethrin Natural products CCC(=O)OC1CC(=C)C2CC3OC3(C)C2C2OC(=O)C(=C)C12 HYJYGLGUBUDSLJ-UHFFFAOYSA-N 0.000 description 1
- 229940070846 pyrethrins Drugs 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 235000019832 sodium triphosphate Nutrition 0.000 description 1
- KZOJQMWTKJDSQJ-UHFFFAOYSA-M sodium;2,3-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 KZOJQMWTKJDSQJ-UHFFFAOYSA-M 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- DAJSVUQLFFJUSX-UHFFFAOYSA-M sodium;dodecane-1-sulfonate Chemical compound [Na+].CCCCCCCCCCCCS([O-])(=O)=O DAJSVUQLFFJUSX-UHFFFAOYSA-M 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000002594 sorbent Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 239000012177 spermaceti Substances 0.000 description 1
- 229940084106 spermaceti Drugs 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 150000008054 sulfonate salts Chemical class 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 230000009469 supplementation Effects 0.000 description 1
- 229960003080 taurine Drugs 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000004953 trihalomethyl group Chemical group 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-I triphosphate(5-) Chemical compound [O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O UNXRWKVEANCORM-UHFFFAOYSA-I 0.000 description 1
- NGCRXXLKJAAUQQ-UHFFFAOYSA-N undec-5-ene Chemical compound CCCCCC=CCCCC NGCRXXLKJAAUQQ-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/10—Aromatic or araliphatic carboxylic acids, or thio analogues thereof; Derivatives thereof
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/30—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings
- C07C57/38—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C61/16—Unsaturated compounds
- C07C61/40—Unsaturated compounds containing halogen
-
- 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
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5442—Aromatic phosphonium compounds (P-C aromatic linkage)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/221,656 US4333950A (en) | 1979-05-24 | 1980-12-31 | (+)-4-Substituted-2-indanol insecticidal ester derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU189743B true HU189743B (en) | 1986-07-28 |
Family
ID=22828742
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU833138D HU189743B (en) | 1980-12-31 | 1981-12-17 | Insecticide or acaricide compositions containing derivatives of /+/-substituted 2-indanole esters as active substances and process for preparing the active substances |
| HU82620A HU185330B (en) | 1980-12-31 | 1981-12-17 | Process for preparing /+/-4-substituted-2-indazoles |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU82620A HU185330B (en) | 1980-12-31 | 1981-12-17 | Process for preparing /+/-4-substituted-2-indazoles |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4333950A (en19) |
| EP (1) | EP0069761B1 (en19) |
| JP (2) | JPS6136823B2 (en19) |
| AU (1) | AU542159B2 (en19) |
| BR (1) | BR8108944A (en19) |
| CA (1) | CA1232613A (en19) |
| DE (1) | DE3171864D1 (en19) |
| DK (1) | DK387182A (en19) |
| ES (1) | ES508427A0 (en19) |
| HU (2) | HU189743B (en19) |
| IE (1) | IE52172B1 (en19) |
| IL (1) | IL64702A (en19) |
| OA (1) | OA07215A (en19) |
| TR (2) | TR21883A (en19) |
| WO (1) | WO1982002321A1 (en19) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2143820B (en) * | 1979-05-24 | 1985-10-02 | Fmc Corp | 4-substituted-2-indanols |
| US4423255A (en) * | 1980-12-31 | 1983-12-27 | Fmc Corporation | (+)-4-Substituted-2-indanols |
| US4429149A (en) | 1980-12-31 | 1984-01-31 | Fmc Corporation | 4-Phenyl-2-indanyl esters of 1R,cis-3-(2-halo-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropanecarboxylic acid |
| US4417078A (en) * | 1980-12-31 | 1983-11-22 | Fmc Corporation | Process for producing (+)-4-substituted-2-indanols |
| US4415748A (en) * | 1981-08-06 | 1983-11-15 | Fmc Corporation | Intermediates for insecticidal synthetic pyrethroids |
| US4552892A (en) * | 1983-03-11 | 1985-11-12 | Fmc Corporation | Acaricidal difluoroethenylcyclopropanecarboxylates |
| DK171797B1 (da) * | 1995-07-21 | 1997-06-02 | Cheminova Agro As | Cyclopropanderivater og fremgangsmåde til fremstilling af cyclopropancarboxylsyrer, ved hvilken disse cyclopropanderivater indgår som mellemprodukter. |
| CN1144778C (zh) * | 1998-10-08 | 2004-04-07 | 住友化学工业株式会社 | 制备环丙烷羧酸酯的方法 |
| GB0017617D0 (en) * | 2000-07-18 | 2000-09-06 | Zeneca Ltd | Chemical process |
| CN106518645A (zh) * | 2016-09-29 | 2017-03-22 | 江苏中能化学科技股份有限公司 | 一种高顺式功夫菊酸的合成工艺 |
| CN109928876A (zh) * | 2017-12-19 | 2019-06-25 | 江苏扬农化工股份有限公司 | 二甲环丙羧酸酯的生产工艺 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3078313A (en) * | 1961-06-15 | 1963-02-19 | Herbert C Brown | Selective hydroboration |
| US3647857A (en) * | 1970-03-16 | 1972-03-07 | Procter & Gamble | Novel esters of chrysanthemic acid and alcohols related to 2-indanol |
| US4024163A (en) * | 1972-05-25 | 1977-05-17 | National Research Development Corporation | Insecticides |
| US4183948A (en) * | 1977-01-24 | 1980-01-15 | Imperial Chemical Industries Limited | Halogenated esters |
| IN150399B (en19) * | 1978-01-20 | 1982-09-25 | Fmc Corp |
-
1980
- 1980-12-31 US US06/221,656 patent/US4333950A/en not_active Expired - Lifetime
-
1981
- 1981-12-14 CA CA000392183A patent/CA1232613A/en not_active Expired
- 1981-12-17 HU HU833138D patent/HU189743B/hu unknown
- 1981-12-17 BR BR8108944A patent/BR8108944A/pt unknown
- 1981-12-17 EP EP82900454A patent/EP0069761B1/en not_active Expired
- 1981-12-17 JP JP57500486A patent/JPS6136823B2/ja not_active Expired
- 1981-12-17 WO PCT/US1981/001690 patent/WO1982002321A1/en active IP Right Grant
- 1981-12-17 HU HU82620A patent/HU185330B/hu unknown
- 1981-12-17 DE DE8282900454T patent/DE3171864D1/de not_active Expired
- 1981-12-17 AU AU80068/82A patent/AU542159B2/en not_active Ceased
- 1981-12-21 IE IE3013/81A patent/IE52172B1/en unknown
- 1981-12-30 TR TR21883A patent/TR21883A/xx unknown
- 1981-12-30 ES ES508427A patent/ES508427A0/es active Granted
- 1981-12-30 TR TR21113A patent/TR21113A/xx unknown
-
1982
- 1982-01-03 IL IL64702A patent/IL64702A/xx unknown
- 1982-08-30 DK DK387182A patent/DK387182A/da not_active Application Discontinuation
- 1982-09-20 OA OA57807A patent/OA07215A/xx unknown
-
1985
- 1985-08-12 JP JP60175984A patent/JPS6144835A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CA1232613A (en) | 1988-02-09 |
| TR21113A (tr) | 1983-09-09 |
| IL64702A (en) | 1984-12-31 |
| AU8006882A (en) | 1982-08-02 |
| OA07215A (fr) | 1984-04-30 |
| AU542159B2 (en) | 1985-02-07 |
| JPS57502167A (en19) | 1982-12-09 |
| IE813013L (en) | 1982-06-30 |
| WO1982002321A1 (en) | 1982-07-22 |
| EP0069761A4 (en) | 1983-05-16 |
| TR21883A (tr) | 1985-10-03 |
| BR8108944A (pt) | 1982-12-14 |
| HU185330B (en) | 1985-01-28 |
| DE3171864D1 (en) | 1985-09-19 |
| JPS6136823B2 (en19) | 1986-08-20 |
| ES8305296A1 (es) | 1983-04-01 |
| EP0069761A1 (en) | 1983-01-19 |
| EP0069761B1 (en) | 1985-08-14 |
| IL64702A0 (en) | 1982-03-31 |
| ES508427A0 (es) | 1983-04-01 |
| DK387182A (da) | 1982-08-30 |
| US4333950A (en) | 1982-06-08 |
| JPS6144835A (ja) | 1986-03-04 |
| IE52172B1 (en) | 1987-07-22 |
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