CA1140141A - Oxyimino-substituted cyclopropanecarboxylate esters, process and intermediates for their manufacture, pesticidal compositions containing them, and their use as pesticides - Google Patents
Oxyimino-substituted cyclopropanecarboxylate esters, process and intermediates for their manufacture, pesticidal compositions containing them, and their use as pesticidesInfo
- Publication number
- CA1140141A CA1140141A CA000326805A CA326805A CA1140141A CA 1140141 A CA1140141 A CA 1140141A CA 000326805 A CA000326805 A CA 000326805A CA 326805 A CA326805 A CA 326805A CA 1140141 A CA1140141 A CA 1140141A
- Authority
- CA
- Canada
- Prior art keywords
- carbon atoms
- group containing
- cis
- alkyl
- substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 17
- 230000000361 pesticidal effect Effects 0.000 title abstract description 14
- 239000000543 intermediate Substances 0.000 title abstract description 11
- 239000000203 mixture Substances 0.000 title description 39
- 239000000575 pesticide Substances 0.000 title description 10
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 title description 9
- 238000004519 manufacturing process Methods 0.000 title description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 73
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 43
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 22
- 239000002253 acid Substances 0.000 claims abstract description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 17
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 15
- 125000005843 halogen group Chemical group 0.000 claims abstract description 15
- 125000003118 aryl group Chemical group 0.000 claims abstract description 12
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 9
- -1 3-phenoxybenzyl Chemical group 0.000 claims description 75
- 150000002148 esters Chemical class 0.000 claims description 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 241000607479 Yersinia pestis Species 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 125000003545 alkoxy 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
- 125000000524 functional group Chemical group 0.000 claims description 2
- 125000003544 oxime group Chemical group 0.000 claims 1
- 150000004820 halides Chemical class 0.000 abstract description 11
- 241000238631 Hexapoda Species 0.000 abstract description 9
- 230000000694 effects Effects 0.000 abstract description 5
- 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 abstract description 4
- 150000003839 salts Chemical class 0.000 abstract description 4
- AFEOKIGLYCQHAZ-UHFFFAOYSA-N (5-benzylfuran-3-yl)methanol Chemical compound OCC1=COC(CC=2C=CC=CC=2)=C1 AFEOKIGLYCQHAZ-UHFFFAOYSA-N 0.000 abstract description 3
- 239000002728 pyrethroid Substances 0.000 abstract description 3
- KGANAERDZBAECK-UHFFFAOYSA-N (3-phenoxyphenyl)methanol Chemical compound OCC1=CC=CC(OC=2C=CC=CC=2)=C1 KGANAERDZBAECK-UHFFFAOYSA-N 0.000 abstract description 2
- 125000005907 alkyl ester group Chemical group 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 42
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- 238000012360 testing method Methods 0.000 description 20
- 150000002923 oximes Chemical group 0.000 description 19
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 239000003921 oil Substances 0.000 description 17
- 239000000243 solution Substances 0.000 description 17
- YMGUBTXCNDTFJI-UHFFFAOYSA-M cyclopropanecarboxylate Chemical compound [O-]C(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-M 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- 150000001298 alcohols Chemical class 0.000 description 11
- 239000000460 chlorine Substances 0.000 description 10
- 231100000419 toxicity Toxicity 0.000 description 10
- 230000001988 toxicity Effects 0.000 description 10
- 231100000167 toxic agent Toxicity 0.000 description 9
- 239000003440 toxic substance Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 235000019341 magnesium sulphate Nutrition 0.000 description 7
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 241000238876 Acari Species 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- 241000255925 Diptera Species 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- 241000255967 Helicoverpa zea Species 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 239000003995 emulsifying agent Substances 0.000 description 5
- 229940073584 methylene chloride Drugs 0.000 description 5
- 239000003381 stabilizer Substances 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 125000003158 alcohol group Chemical group 0.000 description 4
- 230000000875 corresponding effect Effects 0.000 description 4
- DLLJVQNYBYOKGS-UHFFFAOYSA-N ethoxyethane;pentane Chemical compound CCCCC.CCOCC DLLJVQNYBYOKGS-UHFFFAOYSA-N 0.000 description 4
- 239000002917 insecticide Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N methyl alcohol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 238000005507 spraying Methods 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- DSQFSFBBPSALMS-UHFFFAOYSA-N 2-bromo-2-(3-phenoxyphenyl)acetonitrile Chemical compound N#CC(Br)C1=CC=CC(OC=2C=CC=CC=2)=C1 DSQFSFBBPSALMS-UHFFFAOYSA-N 0.000 description 3
- 241001124076 Aphididae Species 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 235000012211 aluminium silicate Nutrition 0.000 description 3
- 229910000323 aluminium silicate Inorganic materials 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000004495 emulsifiable concentrate Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 150000007522 mineralic acids Chemical class 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- BXRUQOMDWYYKSL-IUCAKERBSA-N (1r,3s)-3-(cyclopropylmethoxyiminomethyl)-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound OC(=O)[C@H]1C(C)(C)[C@H]1C=NOCC1CC1 BXRUQOMDWYYKSL-IUCAKERBSA-N 0.000 description 2
- PFVHYZPMYZPQDI-VXKWHMMOSA-N (3-phenoxyphenyl)methyl (1r,3s)-3-(cyclopropylmethoxyiminomethyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound C([C@@H]1C([C@@H]1C(=O)OCC=1C=C(OC=2C=CC=CC=2)C=CC=1)(C)C)=NOCC1CC1 PFVHYZPMYZPQDI-VXKWHMMOSA-N 0.000 description 2
- UJUNUASMYSTBSK-UHFFFAOYSA-N 1-(bromomethyl)-3-phenoxybenzene Chemical compound BrCC1=CC=CC(OC=2C=CC=CC=2)=C1 UJUNUASMYSTBSK-UHFFFAOYSA-N 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- 241000258937 Hemiptera Species 0.000 description 2
- 241000257226 Muscidae Species 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- 241000254152 Sitophilus oryzae Species 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical class [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 241001454293 Tetranychus urticae Species 0.000 description 2
- 240000006677 Vicia faba Species 0.000 description 2
- OUDDCJDNFZOIAH-LIMDNCRJSA-N [cyano-(3-phenoxyphenyl)methyl] (1r,3s)-3-(butoxyiminomethyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CC1(C)[C@@H](C=NOCCCC)[C@H]1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 OUDDCJDNFZOIAH-LIMDNCRJSA-N 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- AFVLVVWMAFSXCK-VMPITWQZSA-N alpha-cyano-4-hydroxycinnamic acid Chemical group OC(=O)C(\C#N)=C\C1=CC=C(O)C=C1 AFVLVVWMAFSXCK-VMPITWQZSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
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- 150000001768 cations Chemical class 0.000 description 2
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- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 2
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- 150000002431 hydrogen Chemical class 0.000 description 2
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- XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 description 2
- 150000002443 hydroxylamines Chemical class 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
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- PWWVUCNNNZKEBY-WDSKDSINSA-N (1r,3s)-3-(methoxyiminomethyl)-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CON=C[C@H]1[C@@H](C(O)=O)C1(C)C PWWVUCNNNZKEBY-WDSKDSINSA-N 0.000 description 1
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- ISKVDROBICOSMM-UHFFFAOYSA-N (3-benzylphenyl)methanol Chemical group OCC1=CC=CC(CC=2C=CC=CC=2)=C1 ISKVDROBICOSMM-UHFFFAOYSA-N 0.000 description 1
- PFVHYZPMYZPQDI-YADHBBJMSA-N (3-phenoxyphenyl)methyl (1r,3r)-3-(cyclopropylmethoxyiminomethyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound C([C@H]1C([C@@H]1C(=O)OCC=1C=C(OC=2C=CC=CC=2)C=CC=1)(C)C)=NOCC1CC1 PFVHYZPMYZPQDI-YADHBBJMSA-N 0.000 description 1
- AFKLSWIRJUJWKY-UHFFFAOYSA-N (3-phenylmethoxyphenyl)methanol Chemical compound OCC1=CC=CC(OCC=2C=CC=CC=2)=C1 AFKLSWIRJUJWKY-UHFFFAOYSA-N 0.000 description 1
- NFEYDQAXVWVFAJ-ROUUACIJSA-N (5-benzylfuran-3-yl)methyl (1r,3s)-3-(methoxyiminomethyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CC1(C)[C@@H](C=NOC)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 NFEYDQAXVWVFAJ-ROUUACIJSA-N 0.000 description 1
- IVGYSSJKFLEVIX-SNAWJCMRSA-N (E)-pyrethrolone Chemical compound CC1=C(C\C=C\C=C)C(=O)CC1O IVGYSSJKFLEVIX-SNAWJCMRSA-N 0.000 description 1
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- 239000000725 suspension Substances 0.000 description 1
- 239000004546 suspension concentrate Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 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
- C07D307/02—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
-
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B24—GRINDING; POLISHING
- B24B—MACHINES, DEVICES, OR PROCESSES FOR GRINDING OR POLISHING; DRESSING OR CONDITIONING OF ABRADING SURFACES; FEEDING OF GRINDING, POLISHING, OR LAPPING AGENTS
- B24B23/00—Portable grinding machines, e.g. hand-guided; Accessories therefor
- B24B23/02—Portable grinding machines, e.g. hand-guided; Accessories therefor with rotating grinding tools; Accessories therefor
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B25—HAND TOOLS; PORTABLE POWER-DRIVEN TOOLS; MANIPULATORS
- B25F—COMBINATION OR MULTI-PURPOSE TOOLS NOT OTHERWISE PROVIDED FOR; DETAILS OR COMPONENTS OF PORTABLE POWER-DRIVEN TOOLS NOT PARTICULARLY RELATED TO THE OPERATIONS PERFORMED AND NOT OTHERWISE PROVIDED FOR
- B25F5/00—Details or components of portable power-driven tools not particularly related to the operations performed and not otherwise provided for
- B25F5/008—Cooling means
Landscapes
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Mechanical Engineering (AREA)
- Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Detergent Compositions (AREA)
- Valve Device For Special Equipments (AREA)
- Iron Core Of Rotating Electric Machines (AREA)
- Fluid-Driven Valves (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US91174378A | 1978-06-02 | 1978-06-02 | |
| US911,743 | 1978-06-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1140141A true CA1140141A (en) | 1983-01-25 |
Family
ID=25430781
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000326805A Expired CA1140141A (en) | 1978-06-02 | 1979-05-02 | Oxyimino-substituted cyclopropanecarboxylate esters, process and intermediates for their manufacture, pesticidal compositions containing them, and their use as pesticides |
Country Status (20)
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4219565A (en) * | 1979-06-26 | 1980-08-26 | Shell Oil Company | Oxyimino-substituted cyclopropanecarboxylate pesticides |
| FR2471369A1 (fr) * | 1979-12-17 | 1981-06-19 | Roussel Uclaf | Nouvelles imines, derivant d'esters d'acides formyl cyclopropane carboxyliques, leur procede de preparation et leur application a la preparation d'esters insecticides |
| US4439446A (en) * | 1981-12-21 | 1984-03-27 | Shell Oil Company | Fluorine-containing oxyiminocyclopropanecarboxylates |
| ZA829332B (en) * | 1981-12-21 | 1983-09-28 | Shell Res Ltd | Fluorophenoxybenzyl esters, their preparation and use as pesticides |
| US4584304A (en) * | 1984-06-08 | 1986-04-22 | Shell Oil Company | 2-pyridinylmethyl oxyiminocyclopropanecarboxylates as pesticides |
| AU754206B2 (en) * | 1998-06-09 | 2002-11-07 | Sumitomo Chemical Company, Limited | Ester compounds |
| JP2002020209A (ja) * | 2000-07-06 | 2002-01-23 | Sumitomo Chem Co Ltd | エステル化合物を含有する蚊の防除剤 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1410080A (en) * | 1972-12-21 | 1975-10-15 | Nat Res Dev | Oxime derivatives of 2,2-dimethyl-3-formyl cyclopropane carboxylic acid and their use as insecticides |
| JPS5511006B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1973-05-07 | 1980-03-21 | ||
| NL178590C (nl) * | 1973-08-15 | 1986-04-16 | Nat Res Dev | Werkwijze voor het bereiden van een insecticide preparaat; werkwijze voor het bereiden van een synthetisch pyrethroide. |
-
1979
- 1979-04-26 DK DK173679A patent/DK158037C/da active IP Right Grant
- 1979-05-02 CA CA000326805A patent/CA1140141A/en not_active Expired
- 1979-05-23 DE DE7979200256T patent/DE2965606D1/de not_active Expired
- 1979-05-23 AT AT79200256T patent/ATE3713T1/de not_active IP Right Cessation
- 1979-05-23 EP EP79200256A patent/EP0005882B1/en not_active Expired
- 1979-05-30 ZA ZA792695A patent/ZA792695B/xx unknown
- 1979-05-31 DD DD79213322A patent/DD144504A5/de unknown
- 1979-05-31 TR TR21275A patent/TR21275A/xx unknown
- 1979-05-31 BR BR7903428A patent/BR7903428A/pt unknown
- 1979-05-31 CS CS793762A patent/CS210690B2/cs unknown
- 1979-05-31 JP JP6691579A patent/JPS54160343A/ja active Pending
- 1979-05-31 PL PL21599679A patent/PL215996A1/xx unknown
- 1979-05-31 AU AU47633/79A patent/AU527266B2/en not_active Expired
- 1979-05-31 IL IL57453A patent/IL57453A0/xx not_active IP Right Cessation
- 1979-05-31 ES ES481127A patent/ES481127A1/es not_active Expired
- 1979-05-31 HU HU79SE1940A patent/HU184523B/hu unknown
- 1979-05-31 PH PH22597A patent/PH16772A/en unknown
- 1979-05-31 YU YU01289/79A patent/YU128979A/xx unknown
- 1979-06-02 OA OA56821A patent/OA06268A/xx unknown
- 1979-08-08 IE IE1068/79A patent/IE48154B1/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DK158037C (da) | 1990-08-13 |
| CS210690B2 (en) | 1982-01-29 |
| DK158037B (da) | 1990-03-19 |
| IL57453A0 (en) | 1979-09-30 |
| YU128979A (en) | 1983-12-31 |
| IE791068L (en) | 1979-12-02 |
| EP0005882B1 (en) | 1983-06-08 |
| AU4763379A (en) | 1979-12-06 |
| DK173679A (da) | 1979-12-04 |
| OA06268A (fr) | 1981-06-30 |
| TR21275A (tr) | 1984-03-15 |
| ATE3713T1 (de) | 1983-06-15 |
| PL215996A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1980-02-11 |
| HU184523B (en) | 1984-09-28 |
| IE48154B1 (en) | 1984-10-17 |
| ZA792695B (en) | 1980-06-25 |
| AU527266B2 (en) | 1983-02-24 |
| JPS54160343A (en) | 1979-12-19 |
| DD144504A5 (de) | 1980-10-22 |
| BR7903428A (pt) | 1980-01-15 |
| EP0005882A1 (en) | 1979-12-12 |
| ES481127A1 (es) | 1980-02-01 |
| PH16772A (en) | 1984-02-22 |
| DE2965606D1 (en) | 1983-07-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |