CH630890A5 - Esters of cyclopropanecarboxylic acids containing a halogenated substituent - Google Patents
Esters of cyclopropanecarboxylic acids containing a halogenated substituent Download PDFInfo
- Publication number
- CH630890A5 CH630890A5 CH742680A CH742680A CH630890A5 CH 630890 A5 CH630890 A5 CH 630890A5 CH 742680 A CH742680 A CH 742680A CH 742680 A CH742680 A CH 742680A CH 630890 A5 CH630890 A5 CH 630890A5
- Authority
- CH
- Switzerland
- Prior art keywords
- cyclopropane
- dimethyl
- carboxylate
- trans
- peaks
- Prior art date
Links
- 150000002148 esters Chemical class 0.000 title claims abstract description 31
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 title claims description 180
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 224
- 150000001875 compounds Chemical class 0.000 claims abstract description 200
- 239000001257 hydrogen Substances 0.000 claims abstract description 149
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 149
- 239000002253 acid Substances 0.000 claims abstract description 115
- -1 furylmethyl Chemical group 0.000 claims abstract description 100
- 239000000460 chlorine Chemical group 0.000 claims abstract description 74
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 53
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 46
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 35
- 229910052794 bromium Chemical group 0.000 claims abstract description 29
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000011737 fluorine Chemical group 0.000 claims abstract description 22
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 22
- 229910052740 iodine Chemical group 0.000 claims abstract description 21
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 19
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 10
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 5
- 239000011630 iodine Chemical group 0.000 claims abstract description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 162
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 70
- 125000003118 aryl group Chemical group 0.000 claims description 55
- 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 claims description 39
- KZYVOZABVXLALY-UHFFFAOYSA-N 4-hydroxy-3-methyl-2-prop-2-enylcyclopent-2-en-1-one Chemical compound CC1=C(CC=C)C(=O)CC1O KZYVOZABVXLALY-UHFFFAOYSA-N 0.000 claims description 35
- 229910052799 carbon Inorganic materials 0.000 claims description 31
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 29
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 22
- KZYVOZABVXLALY-QMMMGPOBSA-N (4s)-4-hydroxy-3-methyl-2-prop-2-enylcyclopent-2-en-1-one Chemical compound CC1=C(CC=C)C(=O)C[C@@H]1O KZYVOZABVXLALY-QMMMGPOBSA-N 0.000 claims description 15
- KGANAERDZBAECK-UHFFFAOYSA-N (3-phenoxyphenyl)methanol Chemical compound OCC1=CC=CC(OC=2C=CC=CC=2)=C1 KGANAERDZBAECK-UHFFFAOYSA-N 0.000 claims description 14
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 13
- 241000039077 Copula Species 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 150000001298 alcohols Chemical class 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 150000003254 radicals Chemical class 0.000 claims description 8
- AFEOKIGLYCQHAZ-UHFFFAOYSA-N (5-benzylfuran-3-yl)methanol Chemical compound OCC1=COC(CC=2C=CC=CC=2)=C1 AFEOKIGLYCQHAZ-UHFFFAOYSA-N 0.000 claims description 7
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 2
- 230000000749 insecticidal effect Effects 0.000 abstract description 29
- 241000238631 Hexapoda Species 0.000 abstract description 28
- 230000000895 acaricidal effect Effects 0.000 abstract description 10
- 241000238876 Acari Species 0.000 abstract description 9
- 230000031709 bromination Effects 0.000 abstract description 7
- 238000005893 bromination reaction Methods 0.000 abstract description 7
- 230000000843 anti-fungal effect Effects 0.000 abstract description 5
- 238000005660 chlorination reaction Methods 0.000 abstract description 4
- 230000026045 iodination Effects 0.000 abstract description 4
- 238000006192 iodination reaction Methods 0.000 abstract description 4
- 229920002554 vinyl polymer Polymers 0.000 abstract description 4
- 230000001069 nematicidal effect Effects 0.000 abstract description 3
- 230000003071 parasitic effect Effects 0.000 abstract description 3
- 241000244206 Nematoda Species 0.000 abstract description 2
- 244000053095 fungal pathogen Species 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 363
- 125000001495 ethyl group Polymers [H]C([H])([H])C([H])([H])* 0.000 description 104
- 238000001228 spectrum Methods 0.000 description 94
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 90
- 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 87
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 83
- 239000000243 solution Substances 0.000 description 81
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 72
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 71
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 70
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 63
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 63
- 230000009102 absorption Effects 0.000 description 59
- 238000010521 absorption reaction Methods 0.000 description 59
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 59
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 51
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 49
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 46
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 45
- 238000004821 distillation Methods 0.000 description 44
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 43
- 238000004458 analytical method Methods 0.000 description 42
- 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 39
- 238000012360 testing method Methods 0.000 description 39
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 36
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 33
- 239000000741 silica gel Substances 0.000 description 33
- 229910002027 silica gel Inorganic materials 0.000 description 33
- 238000004587 chromatography analysis Methods 0.000 description 32
- 238000011282 treatment Methods 0.000 description 28
- 239000011541 reaction mixture Substances 0.000 description 27
- 238000000034 method Methods 0.000 description 26
- 229940126062 Compound A Drugs 0.000 description 25
- 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 25
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 25
- 239000003208 petroleum Substances 0.000 description 25
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 23
- 239000012141 concentrate Substances 0.000 description 22
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 22
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 21
- 239000000047 product Substances 0.000 description 20
- 125000000746 allylic group Chemical group 0.000 description 19
- 230000000694 effects Effects 0.000 description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 17
- 241000786363 Rhampholeon spectrum Species 0.000 description 17
- 239000012074 organic phase Substances 0.000 description 17
- 238000010992 reflux Methods 0.000 description 17
- 231100000111 LD50 Toxicity 0.000 description 16
- 241001342522 Vampyrum spectrum Species 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 241000257226 Muscidae Species 0.000 description 15
- 238000002983 circular dichroism Methods 0.000 description 14
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 13
- 239000003795 chemical substances by application Substances 0.000 description 13
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 12
- 150000007513 acids Chemical class 0.000 description 12
- 230000032050 esterification Effects 0.000 description 12
- 238000005886 esterification reaction Methods 0.000 description 12
- 239000004480 active ingredient Substances 0.000 description 11
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 11
- 235000013601 eggs Nutrition 0.000 description 11
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 11
- 235000019341 magnesium sulphate Nutrition 0.000 description 11
- 239000000843 powder Substances 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- 238000005507 spraying Methods 0.000 description 10
- 241001465754 Metazoa Species 0.000 description 9
- 239000000642 acaricide Substances 0.000 description 9
- 241000256250 Spodoptera littoralis Species 0.000 description 8
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- 239000000284 extract Substances 0.000 description 8
- 239000000377 silicon dioxide Substances 0.000 description 8
- 238000004809 thin layer chromatography Methods 0.000 description 8
- 230000000699 topical effect Effects 0.000 description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
- 210000000038 chest Anatomy 0.000 description 7
- 239000012043 crude product Substances 0.000 description 7
- 230000001418 larval effect Effects 0.000 description 7
- MTJGVAJYTOXFJH-UHFFFAOYSA-N 3-aminonaphthalene-1,5-disulfonic acid Chemical class C1=CC=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 MTJGVAJYTOXFJH-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
- 241000254179 Sitophilus granarius Species 0.000 description 6
- 241001454293 Tetranychus urticae Species 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 6
- 230000001476 alcoholic effect Effects 0.000 description 6
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 6
- 230000001665 lethal effect Effects 0.000 description 6
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- 239000005645 nematicide Substances 0.000 description 6
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
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- FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 5
- 241000282472 Canis lupus familiaris Species 0.000 description 5
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 5
- 241000254113 Tribolium castaneum Species 0.000 description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 5
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- VOEOAOWTEZOVCB-ZZKAVYKESA-N (1S,3S)-3-(2,2-dibromo-1,2-dichloroethyl)-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1([C@H]([C@@H]1C(C(Cl)(Br)Br)Cl)C(=O)O)C VOEOAOWTEZOVCB-ZZKAVYKESA-N 0.000 description 4
- GXUQMKBQDGPMKZ-CQSZACIVSA-N (2s)-2-hydroxy-2-(3-phenoxyphenyl)acetonitrile Chemical compound N#C[C@@H](O)C1=CC=CC(OC=2C=CC=CC=2)=C1 GXUQMKBQDGPMKZ-CQSZACIVSA-N 0.000 description 4
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
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- VOEOAOWTEZOVCB-OVEKKEMJSA-N (1r,3s)-3-(2,2-dibromo-1,2-dichloroethyl)-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)[C@@H](C(Cl)C(Cl)(Br)Br)[C@H]1C(O)=O VOEOAOWTEZOVCB-OVEKKEMJSA-N 0.000 description 3
- MDIQXIJPQWLFSD-XINAWCOVSA-N (1r,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-XINAWCOVSA-N 0.000 description 3
- 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 description 3
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- LLMLSUSAKZVFOA-XINAWCOVSA-N (1r,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-XINAWCOVSA-N 0.000 description 2
- 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 description 2
- 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
- NUQSJBAQSZZDJA-UHFFFAOYSA-N 2,2-dimethyl-3-(1,2,2,2-tetrachloroethyl)cyclopropane-1-carboxylic acid Chemical compound CC1(C)C(C(Cl)C(Cl)(Cl)Cl)C1C(O)=O NUQSJBAQSZZDJA-UHFFFAOYSA-N 0.000 description 2
- GXUQMKBQDGPMKZ-UHFFFAOYSA-N 2-hydroxy-2-(3-phenoxyphenyl)acetonitrile Chemical compound N#CC(O)C1=CC=CC(OC=2C=CC=CC=2)=C1 GXUQMKBQDGPMKZ-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- VOEOAOWTEZOVCB-UHFFFAOYSA-N 3-(2,2-dibromo-1,2-dichloroethyl)-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)C(C(Cl)C(Cl)(Br)Br)C1C(O)=O VOEOAOWTEZOVCB-UHFFFAOYSA-N 0.000 description 2
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 2
- 238000012935 Averaging Methods 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
- C07D209/49—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide 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
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- 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
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/42—Singly bound oxygen 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)
- 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 |
|---|---|---|---|
| FR7722078A FR2398041A2 (fr) | 1977-07-19 | 1977-07-19 | Esters d'acides cyclopropane carboxylique comportant un substituant polyhalogene, procede de preparation et leur application comme insecticides, acaricides, nematicides et comme medicaments veterinaires |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH630890A5 true CH630890A5 (en) | 1982-07-15 |
Family
ID=9193492
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH742680A CH630890A5 (en) | 1977-07-19 | 1980-10-03 | Esters of cyclopropanecarboxylic acids containing a halogenated substituent |
| CH742780A CH630601A5 (en) | 1977-07-19 | 1980-10-03 | Cyclopropanecarboxylic acids containing a polyhalogenated group |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH742780A CH630601A5 (en) | 1977-07-19 | 1980-10-03 | Cyclopropanecarboxylic acids containing a polyhalogenated group |
Country Status (3)
| Country | Link |
|---|---|
| CH (2) | CH630890A5 (enrdf_load_stackoverflow) |
| CZ (1) | CZ278747B6 (enrdf_load_stackoverflow) |
| FR (1) | FR2398041A2 (enrdf_load_stackoverflow) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2484256B1 (fr) * | 1979-06-29 | 1986-10-24 | Roussel Uclaf | Procede de lutte contre les parasites des animaux a sang chaud |
| FR2471187A1 (fr) * | 1979-12-10 | 1981-06-19 | Roussel Uclaf | Nouvelles compositions destinees a la lutte contre les parasites des animaux a sang chaud |
| FR2463584A1 (fr) * | 1979-08-17 | 1981-02-27 | Roussel Uclaf | Compositions insecticides lave-vitre et leur application a la lutte contre les insectes ailes des locaux |
| FR2469403A1 (fr) * | 1979-11-14 | 1981-05-22 | Roussel Uclaf | Esters d'alcools heterocycliques, leurs procedes de preparation et les compositions les renfermant |
| DE3004092A1 (de) * | 1980-02-05 | 1981-08-13 | Bayer Ag, 5090 Leverkusen | Substituierte 3-(1,2-dibrom-alkyl)- 2,2-dimethyl-cyclopropan-1-carbonsaeureester, verfahren sowie zwischenprodukte zu ihrer herstellung und ihre verwendung in schaedlingsbekaempfungsmitteln |
-
1977
- 1977-07-19 FR FR7722078A patent/FR2398041A2/fr active Granted
- 1977-09-21 CZ CS776114A patent/CZ278747B6/cs unknown
-
1980
- 1980-10-03 CH CH742680A patent/CH630890A5/fr not_active IP Right Cessation
- 1980-10-03 CH CH742780A patent/CH630601A5/fr not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CZ278747B6 (en) | 1994-06-15 |
| FR2398041B2 (enrdf_load_stackoverflow) | 1981-02-13 |
| CZ611477A3 (en) | 1994-02-16 |
| FR2398041A2 (fr) | 1979-02-16 |
| CH630601A5 (en) | 1982-06-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |