IL22718A - 4-and 7-benzofuranyl carbamates and thionocarbamates - Google Patents
4-and 7-benzofuranyl carbamates and thionocarbamatesInfo
- Publication number
- IL22718A IL22718A IL22718A IL2271865A IL22718A IL 22718 A IL22718 A IL 22718A IL 22718 A IL22718 A IL 22718A IL 2271865 A IL2271865 A IL 2271865A IL 22718 A IL22718 A IL 22718A
- Authority
- IL
- Israel
- Prior art keywords
- dihydro
- dimethyl
- benzofuranyl
- compound
- carbamate
- Prior art date
Links
- -1 7-benzofuranyl carbamates Chemical class 0.000 title claims description 27
- 239000000203 mixture Substances 0.000 claims description 40
- 238000000034 method Methods 0.000 claims description 31
- 150000001875 compounds Chemical class 0.000 claims description 28
- 238000007363 ring formation reaction Methods 0.000 claims description 8
- WDZLZKSUBSXWID-UHFFFAOYSA-N 2,3-dihydro-1-benzofuran-2-ol Chemical compound C1=CC=C2OC(O)CC2=C1 WDZLZKSUBSXWID-UHFFFAOYSA-N 0.000 claims description 7
- 230000000694 effects Effects 0.000 claims description 7
- 230000008707 rearrangement Effects 0.000 claims description 7
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 6
- DUEPRVBVGDRKAG-UHFFFAOYSA-N carbofuran Chemical compound CNC(=O)OC1=CC=CC2=C1OC(C)(C)C2 DUEPRVBVGDRKAG-UHFFFAOYSA-N 0.000 claims description 6
- 229940125782 compound 2 Drugs 0.000 claims description 6
- 241000244206 Nematoda Species 0.000 claims description 5
- 230000032050 esterification Effects 0.000 claims description 4
- 238000005886 esterification reaction Methods 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 239000004606 Fillers/Extenders Substances 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000000575 pesticide Substances 0.000 claims description 3
- FMGLKNCPXAFVRR-UHFFFAOYSA-N (2,2,4-trimethyl-3h-1-benzofuran-7-yl) n-methylcarbamate Chemical compound CNC(=O)OC1=CC=C(C)C2=C1OC(C)(C)C2 FMGLKNCPXAFVRR-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 230000001069 nematicidal effect Effects 0.000 claims description 2
- 239000005645 nematicide Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 241000238421 Arthropoda Species 0.000 claims 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000243 solution Substances 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- 230000000361 pesticidal effect Effects 0.000 description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- 238000002360 preparation method Methods 0.000 description 16
- 238000004458 analytical method Methods 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 241000462639 Epilachna varivestis Species 0.000 description 14
- 239000007787 solid Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 229910001868 water Inorganic materials 0.000 description 14
- 238000002844 melting Methods 0.000 description 13
- 230000008018 melting Effects 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- 241000253994 Acyrthosiphon pisum Species 0.000 description 10
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- 241000258913 Oncopeltus fasciatus Species 0.000 description 10
- 231100000167 toxic agent Toxicity 0.000 description 10
- 239000003440 toxic substance Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 241000238631 Hexapoda Species 0.000 description 7
- 241001521235 Spodoptera eridania Species 0.000 description 7
- 238000001953 recrystallisation Methods 0.000 description 7
- WJGPNUBJBMCRQH-UHFFFAOYSA-N 2,2-dimethyl-2,3-dihydro-1-benzofuran-7-ol Chemical compound C1=CC(O)=C2OC(C)(C)CC2=C1 WJGPNUBJBMCRQH-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- 239000012141 concentrate Substances 0.000 description 6
- 235000008504 concentrate Nutrition 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- 239000002689 soil Substances 0.000 description 6
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 239000002270 dispersing agent Substances 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 125000005394 methallyl group Chemical group 0.000 description 5
- 238000010998 test method Methods 0.000 description 5
- LFIQOFYSVSBJNH-UHFFFAOYSA-N (2,2-dimethyl-3h-1-benzofuran-7-yl) carbonochloridate Chemical compound C1=CC(OC(Cl)=O)=C2OC(C)(C)CC2=C1 LFIQOFYSVSBJNH-UHFFFAOYSA-N 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 4
- 206010061217 Infestation Diseases 0.000 description 4
- 241000257226 Muscidae Species 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 241001454293 Tetranychus urticae Species 0.000 description 4
- 241000607479 Yersinia pestis Species 0.000 description 4
- 239000000538 analytical sample Substances 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 239000004927 clay Substances 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 229940086542 triethylamine Drugs 0.000 description 4
- AAXBKJXGVXNSHI-UHFFFAOYSA-N 2-(2-methylprop-2-enoxy)phenol Chemical compound CC(=C)COC1=CC=CC=C1O AAXBKJXGVXNSHI-UHFFFAOYSA-N 0.000 description 3
- OHXAOPZTJOUYKM-UHFFFAOYSA-N 3-Chloro-2-methylpropene Chemical compound CC(=C)CCl OHXAOPZTJOUYKM-UHFFFAOYSA-N 0.000 description 3
- 238000003547 Friedel-Crafts alkylation reaction Methods 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 125000003118 aryl group Chemical class 0.000 description 3
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 230000000749 insecticidal effect Effects 0.000 description 3
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000010561 standard procedure Methods 0.000 description 3
- 230000009885 systemic effect Effects 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- YHAROSAFXOQKCZ-UHFFFAOYSA-N 1-benzofuran-2-ol Chemical class C1=CC=C2OC(O)=CC2=C1 YHAROSAFXOQKCZ-UHFFFAOYSA-N 0.000 description 2
- VHVGYMZOFGBRGP-UHFFFAOYSA-N 2,2,4-trimethyl-3H-1-benzofuran-7-ol Chemical compound CC1(OC2=C(C1)C(=CC=C2O)C)C VHVGYMZOFGBRGP-UHFFFAOYSA-N 0.000 description 2
- PBVLQQYOZVYUQF-UHFFFAOYSA-N 2,2-dimethyl-3h-1-benzofuran-4-ol Chemical compound C1=CC=C(O)C2=C1OC(C)(C)C2 PBVLQQYOZVYUQF-UHFFFAOYSA-N 0.000 description 2
- JNYKOGUXPNAUIB-UHFFFAOYSA-N 2,3-dihydro-1-benzofuran-5-ol Chemical class OC1=CC=C2OCCC2=C1 JNYKOGUXPNAUIB-UHFFFAOYSA-N 0.000 description 2
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- 241000238657 Blattella germanica Species 0.000 description 2
- 241001674044 Blattodea Species 0.000 description 2
- ZIIPAHJBCORHNP-UHFFFAOYSA-N CC(C)(C1)OC2=C1C=CC=C2OC(NC)=S Chemical compound CC(C)(C1)OC2=C1C=CC=C2OC(NC)=S ZIIPAHJBCORHNP-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 238000003747 Grignard reaction Methods 0.000 description 2
- 241000243785 Meloidogyne javanica Species 0.000 description 2
- 241000257159 Musca domestica Species 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 244000046052 Phaseolus vulgaris Species 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- 240000003768 Solanum lycopersicum Species 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 150000004791 alkyl magnesium halides Chemical class 0.000 description 2
- 229960000892 attapulgite Drugs 0.000 description 2
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 239000004495 emulsifiable concentrate Substances 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 230000012010 growth Effects 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 2
- IIFCLXHRIYTHPV-UHFFFAOYSA-N methyl 2,4-dihydroxybenzoate Chemical compound COC(=O)C1=CC=C(O)C=C1O IIFCLXHRIYTHPV-UHFFFAOYSA-N 0.000 description 2
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229910052625 palygorskite Inorganic materials 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- POSICDHOUBKJKP-UHFFFAOYSA-N prop-2-enoxybenzene Chemical class C=CCOC1=CC=CC=C1 POSICDHOUBKJKP-UHFFFAOYSA-N 0.000 description 2
- 238000001304 sample melting Methods 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000012258 stirred mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000012085 test solution Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- UVYPQRKDBIOLSU-UHFFFAOYSA-N (2,2-dimethyl-3H-1-benzofuran-7-yl) N-prop-2-ynylcarbamate Chemical compound C(C#C)NC(OC1=CC=CC=2CC(OC21)(C)C)=O UVYPQRKDBIOLSU-UHFFFAOYSA-N 0.000 description 1
- PEVTXQAJXMYNDJ-UHFFFAOYSA-N (2,2-dimethyl-3h-1-benzofuran-3-yl) n-methylcarbamate Chemical compound C1=CC=C2OC(C)(C)C(OC(=O)NC)C2=C1 PEVTXQAJXMYNDJ-UHFFFAOYSA-N 0.000 description 1
- QTBBEJJXBYGFAP-UHFFFAOYSA-N (2,2-dimethyl-3h-1-benzofuran-7-yl) carbamate Chemical compound C1=CC(OC(N)=O)=C2OC(C)(C)CC2=C1 QTBBEJJXBYGFAP-UHFFFAOYSA-N 0.000 description 1
- YOUOUQFUYLGZRE-UHFFFAOYSA-N (2,2-dimethyl-3h-1-benzofuran-7-yl) n-ethylcarbamate Chemical compound CCNC(=O)OC1=CC=CC2=C1OC(C)(C)C2 YOUOUQFUYLGZRE-UHFFFAOYSA-N 0.000 description 1
- OWFJMIVZYSDULZ-PXOLEDIWSA-N (4s,4ar,5s,5ar,6s,12ar)-4-(dimethylamino)-1,5,6,10,11,12a-hexahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide Chemical compound C1=CC=C2[C@](O)(C)[C@H]3[C@H](O)[C@H]4[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]4(O)C(=O)C3=C(O)C2=C1O OWFJMIVZYSDULZ-PXOLEDIWSA-N 0.000 description 1
- SSUFJVXUMQIJAX-UHFFFAOYSA-N 1-benzofuran-2-yl carbamate Chemical class C1=CC=C2OC(OC(=O)N)=CC2=C1 SSUFJVXUMQIJAX-UHFFFAOYSA-N 0.000 description 1
- LVKKPBPHGILWOM-UHFFFAOYSA-N 1-benzofuran-7-yl n-methylcarbamate Chemical compound CNC(=O)OC1=CC=CC2=C1OC=C2 LVKKPBPHGILWOM-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- SPYQOXKBNGLMCP-UHFFFAOYSA-N 2,2,5-trimethyl-3H-1-benzofuran-7-ol Chemical compound CC1(OC2=C(C1)C=C(C=C2O)C)C SPYQOXKBNGLMCP-UHFFFAOYSA-N 0.000 description 1
- LPXHPAYRONCQIF-UHFFFAOYSA-N 2-(2-hydroxyphenoxy)acetic acid Chemical class OC(=O)COC1=CC=CC=C1O LPXHPAYRONCQIF-UHFFFAOYSA-N 0.000 description 1
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
- GSLTVFIVJMCNBH-UHFFFAOYSA-N 2-isocyanatopropane Chemical compound CC(C)N=C=O GSLTVFIVJMCNBH-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- KKFPNGHRVSRHOC-UHFFFAOYSA-N 3-chloro-1-benzofuran-2-ol Chemical compound ClC1=C(OC2=C1C=CC=C2)O KKFPNGHRVSRHOC-UHFFFAOYSA-N 0.000 description 1
- VQTUMNNCKYTZSR-UHFFFAOYSA-N 3-hydroxy-3h-1-benzofuran-2-one Chemical compound C1=CC=C2C(O)C(=O)OC2=C1 VQTUMNNCKYTZSR-UHFFFAOYSA-N 0.000 description 1
- PYXLGMKGMXVZRX-UHFFFAOYSA-N 4-hydroxy-2,2-dimethyl-3h-1-benzofuran-5-carboxylic acid Chemical compound C1=CC(C(O)=O)=C(O)C2=C1OC(C)(C)C2 PYXLGMKGMXVZRX-UHFFFAOYSA-N 0.000 description 1
- MXNOQGPYVFHNED-UHFFFAOYSA-N 7-(hydroxymethyl)chromen-2-one Chemical compound C1=CC(=O)OC2=CC(CO)=CC=C21 MXNOQGPYVFHNED-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
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- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 101100476962 Drosophila melanogaster Sirup gene Proteins 0.000 description 1
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- 238000005481 NMR spectroscopy Methods 0.000 description 1
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- 239000002250 absorbent Substances 0.000 description 1
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- GZCGUPFRVQAUEE-SLPGGIOYSA-N aldehydo-D-glucose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-SLPGGIOYSA-N 0.000 description 1
- 125000005336 allyloxy group Chemical group 0.000 description 1
- 150000004645 aluminates Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Substances [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- 239000011362 coarse particle Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 125000005117 dialkylcarbamoyl group Chemical group 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 150000005205 dihydroxybenzenes Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 150000002168 ethanoic acid esters Chemical class 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- CAHFMFXUMHYLDW-UHFFFAOYSA-N furan-2-yl n-methylcarbamate Chemical compound CNC(=O)OC1=CC=CO1 CAHFMFXUMHYLDW-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 229910003480 inorganic solid Inorganic materials 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 150000002540 isothiocyanates Chemical class 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 235000014666 liquid concentrate Nutrition 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical class [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 235000011160 magnesium carbonates Nutrition 0.000 description 1
- VJVSRJVELXSXAE-UHFFFAOYSA-N methyl 4-hydroxy-2,2-dimethyl-3h-1-benzofuran-5-carboxylate Chemical compound COC(=O)C1=CC=C2OC(C)(C)CC2=C1O VJVSRJVELXSXAE-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- JKANAVGODYYCQF-UHFFFAOYSA-N prop-2-yn-1-amine Chemical compound NCC#C JKANAVGODYYCQF-UHFFFAOYSA-N 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000006462 rearrangement reaction Methods 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 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
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 235000001508 sulfur Nutrition 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical class [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000002256 xylenyl group Chemical class C1(C(C=CC=C1)C)(C)* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/86—Benzo [b] furans; Hydrogenated benzo [b] furans with an oxygen atom directly attached in position 7
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Furan Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US339612A US3474171A (en) | 1964-01-23 | 1964-01-23 | 2,2-dimethyl-2,3-dihydrobenzofuranyl-7-n-methylcarbamate |
| US403324A US3474170A (en) | 1964-01-23 | 1964-10-12 | Pesticidal carbamates of dihydrobenzofuranols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL22718A true IL22718A (en) | 1970-01-29 |
Family
ID=26991711
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL22718A IL22718A (en) | 1964-01-23 | 1965-01-03 | 4-and 7-benzofuranyl carbamates and thionocarbamates |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3474170A (is") |
| AT (1) | AT276851B (is") |
| BE (1) | BE658194A (is") |
| CH (1) | CH478525A (is") |
| DE (1) | DE1542879B2 (is") |
| DK (1) | DK117775B (is") |
| ES (1) | ES308421A1 (is") |
| FR (1) | FR1436588A (is") |
| GB (1) | GB1099691A (is") |
| IL (1) | IL22718A (is") |
| LU (1) | LU47823A1 (is") |
| NL (1) | NL148605B (is") |
| SE (1) | SE346205B (is") |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3419579A (en) * | 1966-02-23 | 1968-12-31 | Fmc Corp | Synthesis of 2,3-dihydro-2,2-dimethyl-7-benzofuranol |
| US3876667A (en) * | 1971-11-08 | 1975-04-08 | Ici Australia Ltd | Synthesis of 2,3-dihydro-2,2-dimethyl-7-benzofuranyl-n-methyl carbamate starting from ortho-isopropylphenol and methallyl halide |
| US4215115A (en) * | 1976-11-24 | 1980-07-29 | Fmc Corporation | Nematicidal phosphorodithioate |
| US4201786A (en) * | 1977-05-27 | 1980-05-06 | Union Carbide Corporation | Water soluble pesticidal quaternary ammonium salt compounds |
| US4118400A (en) * | 1977-09-22 | 1978-10-03 | Fmc Corporation | Process for preparing 2,3-dihydro-7-benzofuranols and benzodioxole intermediate therefor |
| EP0007719A3 (en) * | 1978-07-29 | 1980-05-14 | Fbc Limited | Cyanbenzofuran derivatives, processes for their preparation and their use in herbicidal compositions; cyanobenzene, benzodioxepine, benzodioxaphosphepine and benzodioxathiepine derivatives |
| IL58661A (en) * | 1978-11-30 | 1983-11-30 | Philagro Sa | Process for the preparation of 2,3-dihydro-2,2-dimethyl-7-hydroxybenzofuran |
| FR2461708A1 (fr) * | 1979-07-18 | 1981-02-06 | Rhone Poulenc Agrochimie | Preparation de dihydrodimethylhydroxy-7 benzofurane |
| DE2932458A1 (de) * | 1979-08-10 | 1981-02-26 | Bayer Ag | Herstellung von monoalkylethern von hydroxyphenolen und deren umwandlung zu hydroxycumaranen |
| FR2470768A1 (fr) * | 1979-12-07 | 1981-06-12 | Rhone Poulenc Agrochimie | Procede de preparation de derives de benzofuranne |
| US4465868A (en) * | 1981-07-17 | 1984-08-14 | Otsuka Kagaku Yakuhin Kabushiki Kaisha | Process for preparing o-methallyloxyphenol |
| US4451662A (en) * | 1981-09-01 | 1984-05-29 | Otsuka Kagaku Yakuhin Kabushiki Kaisha | Process for preparing 2,3-dihydro-2,2-dimethyl-7-hydroxybenzofuran |
| US4419350A (en) * | 1981-11-05 | 1983-12-06 | Stauffer Chemical Company | Carbofuran compositions for problem soils |
| US4380654A (en) * | 1982-02-18 | 1983-04-19 | Fmc Corporation | Process for preparation of 2,3-dihydro-2,2-dimethyl-7-hydroxybenzofuran |
| HU191184B (en) * | 1982-07-09 | 1987-01-28 | Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt,Hu | Stabilized herbicide suspension |
| IT1199987B (it) * | 1983-02-04 | 1989-01-05 | Brichima Spa | Processo per la produzione di derivati benzofuranici |
| US4639536A (en) * | 1984-08-30 | 1987-01-27 | Union Carbide Corporation | Intermediate, its synthesis, and its use in a process for the preparation of 2,3-dihydro-2,2-dimethyl-7-hydroxybenzofuran |
| HU207197B (en) * | 1987-07-16 | 1993-03-29 | Chinoin Gyogyszer Es Vegyeszet | Plant protecting solution and aquous suspension containing water insoluble active component |
| US4982012A (en) * | 1987-12-18 | 1991-01-01 | Fmc Corporation | Two phase process for preparing 2-methallyloxyphenol from catechol |
| US4851587A (en) * | 1988-05-31 | 1989-07-25 | Fmc Corporation | Single solvent process for preparing 2-methallyloxy-phenol from catechol |
| US4987233A (en) * | 1988-06-15 | 1991-01-22 | Eli Lilly And Company | Process for preparing herbicidal ureas and insecticidal carbamates and carbamate derivatives |
| US7671201B2 (en) * | 2003-04-30 | 2010-03-02 | Fmc Corporation | Phenyl substituted cyclic derivatives |
| DE102007045955A1 (de) | 2007-09-26 | 2009-04-09 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| CN102395271A (zh) | 2009-03-25 | 2012-03-28 | 拜尔农作物科学股份公司 | 具有杀虫和杀螨特性的活性化合物结合物 |
| MX338489B (es) | 2010-12-06 | 2016-04-18 | Autifony Therapeuticts Ltd | Derivados de hidantoina utiles como inhibidores de kv3. |
| CN104496973B (zh) * | 2015-01-23 | 2016-11-30 | 邵阳学院 | 呋喃酚丙烯酮衍生物作为杀虫剂的应用 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2362479A (en) * | 1943-08-04 | 1944-11-14 | Goodrich Co B F | Antioxidant for rubber |
-
1964
- 1964-10-12 US US403324A patent/US3474170A/en not_active Expired - Lifetime
-
1965
- 1965-01-03 IL IL22718A patent/IL22718A/en unknown
- 1965-01-12 BE BE658194A patent/BE658194A/xx unknown
- 1965-01-12 NL NL656500340A patent/NL148605B/xx not_active IP Right Cessation
- 1965-01-13 FR FR1836A patent/FR1436588A/fr not_active Expired
- 1965-01-20 CH CH1286167A patent/CH478525A/de not_active IP Right Cessation
- 1965-01-20 AT AT42365A patent/AT276851B/de not_active IP Right Cessation
- 1965-01-22 DE DE1965F0049578 patent/DE1542879B2/de active Granted
- 1965-01-22 ES ES0308421A patent/ES308421A1/es not_active Expired
- 1965-01-22 GB GB2831/65A patent/GB1099691A/en not_active Expired
- 1965-01-22 LU LU47823A patent/LU47823A1/xx unknown
- 1965-01-22 DK DK34765AA patent/DK117775B/da unknown
- 1965-01-22 SE SE6292/67A patent/SE346205B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE1542879A1 (de) | 1970-06-04 |
| DK117775B (da) | 1970-06-01 |
| CH478525A (de) | 1969-09-30 |
| DE1542879B2 (de) | 1977-04-07 |
| US3474170A (en) | 1969-10-21 |
| GB1099691A (en) | 1968-01-17 |
| LU47823A1 (is") | 1965-03-22 |
| SE346205B (is") | 1972-07-03 |
| AT276851B (de) | 1969-12-10 |
| ES308421A1 (es) | 1965-05-16 |
| NL6500340A (is") | 1965-07-26 |
| NL148605B (nl) | 1976-02-16 |
| FR1436588A (fr) | 1966-04-29 |
| BE658194A (is") | 1965-07-12 |
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