CS269991B2 - Insecticide and acaricide and method of active substances production - Google Patents

Insecticide and acaricide and method of active substances production Download PDF

Info

Publication number: CS269991B2
Authority: CS; Czechoslovakia
Prior art keywords: formula; nmr; carbon atoms; compound; methylbutyrate
Prior art date: 1985-12-23

Application number

CS869701A

Other languages

Czech (cs)

English (en)

Other versions

CS970186A2 (en

Inventor

Alan J Whittle

Roger Salmon

Edward Mcdonald

Original Assignee

Ici Plc

Priority date (The priority date 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 date listed.)

1985-12-23

Filing date

1986-12-22

Publication date

1990-05-14

1986-12-22 Application filed by Ici Plc filed Critical Ici Plc

1989-09-12 Publication of CS970186A2 publication Critical patent/CS970186A2/cs

1990-05-14 Publication of CS269991B2 publication Critical patent/CS269991B2/cs

Links

230000000895 acaricidal effect Effects 0.000 title claims abstract description 8
238000000034 method Methods 0.000 title claims description 54
239000002917 insecticide Substances 0.000 title abstract description 12
239000000642 acaricide Substances 0.000 title abstract description 4
239000013543 active substance Substances 0.000 title description 8
238000004519 manufacturing process Methods 0.000 title description 5
150000001875 compounds Chemical class 0.000 claims abstract description 107
239000002253 acid Substances 0.000 claims abstract description 19
239000001257 hydrogen Substances 0.000 claims abstract description 12
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 12
125000000217 alkyl group Chemical group 0.000 claims abstract description 11
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
239000000203 mixture Substances 0.000 claims description 83
238000002360 preparation method Methods 0.000 claims description 65
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 33
125000004432 carbon atom Chemical group C* 0.000 claims description 24
239000004480 active ingredient Substances 0.000 claims description 15
125000003545 alkoxy group Chemical group 0.000 claims description 10
229910052736 halogen Inorganic materials 0.000 claims description 10
150000002367 halogens Chemical class 0.000 claims description 10
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 9
125000005843 halogen group Chemical group 0.000 claims description 8
230000000749 insecticidal effect Effects 0.000 claims description 6
239000002585 base Substances 0.000 claims description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
229910052757 nitrogen Inorganic materials 0.000 claims description 5
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 5
125000005907 alkyl ester group Chemical group 0.000 claims description 4
150000004820 halides Chemical class 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
229910052783 alkali metal Inorganic materials 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
239000003377 acid catalyst Substances 0.000 claims description 2
125000003342 alkenyl group Chemical group 0.000 claims description 2
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
125000000304 alkynyl group Chemical group 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
239000012024 dehydrating agents‎ Substances 0.000 claims description 2
125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 2
125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
125000000262 haloalkenyl group Chemical group 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
150000003242 quaternary ammonium salts Chemical class 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
239000011593 sulfur Chemical group 0.000 claims description 2
238000005809 transesterification reaction Methods 0.000 claims description 2
150000001340 alkali metals Chemical class 0.000 claims 1
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
239000000543 intermediate Substances 0.000 abstract description 17
150000002148 esters Chemical class 0.000 abstract description 8
ZXQYGBMAQZUVMI-UNOMPAQXSA-N cyhalothrin Chemical compound CC1(C)C(\C=C(/Cl)C(F)(F)F)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 ZXQYGBMAQZUVMI-UNOMPAQXSA-N 0.000 abstract description 2
125000001475 halogen functional group Chemical group 0.000 abstract 2
LLMLSUSAKZVFOA-UHFFFAOYSA-N 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(O)=O LLMLSUSAKZVFOA-UHFFFAOYSA-N 0.000 abstract 1
125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 abstract 1
150000003230 pyrimidines Chemical class 0.000 abstract 1
-1 2-pentyl Chemical group 0.000 description 128
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 108
238000005160 1H NMR spectroscopy Methods 0.000 description 89
239000007788 liquid Substances 0.000 description 82
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 76
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 57
239000000243 solution Substances 0.000 description 54
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 50
239000002904 solvent Substances 0.000 description 33
241000607479 Yersinia pestis Species 0.000 description 32
238000006243 chemical reaction Methods 0.000 description 32
239000011541 reaction mixture Substances 0.000 description 32
238000004817 gas chromatography Methods 0.000 description 31
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
239000000047 product Substances 0.000 description 28
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
230000014759 maintenance of location Effects 0.000 description 25
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 22
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 20
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
150000001793 charged compounds Chemical class 0.000 description 19
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 19
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 16
239000012044 organic layer Substances 0.000 description 15
230000000694 effects Effects 0.000 description 14
238000001704 evaporation Methods 0.000 description 14
239000003208 petroleum Substances 0.000 description 14
239000007787 solid Substances 0.000 description 14
238000003756 stirring Methods 0.000 description 14
238000005481 NMR spectroscopy Methods 0.000 description 13
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 13
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
239000012267 brine Substances 0.000 description 12
239000003480 eluent Substances 0.000 description 12
125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 12
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
238000012360 testing method Methods 0.000 description 12
230000008020 evaporation Effects 0.000 description 11
239000000725 suspension Substances 0.000 description 11
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
238000010898 silica gel chromatography Methods 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 9
QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 9
239000000460 chlorine Substances 0.000 description 9
239000000284 extract Substances 0.000 description 9
239000000126 substance Substances 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
241000238631 Hexapoda Species 0.000 description 8
238000000746 purification Methods 0.000 description 8
230000035484 reaction time Effects 0.000 description 8
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
229910000041 hydrogen chloride Inorganic materials 0.000 description 7
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
229940057995 liquid paraffin Drugs 0.000 description 7
238000010992 reflux Methods 0.000 description 7
229920000742 Cotton Polymers 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
150000007513 acids Chemical class 0.000 description 6
238000009835 boiling Methods 0.000 description 6
239000012299 nitrogen atmosphere Substances 0.000 description 6
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 6
CWPBWQMSTGAQSS-UHFFFAOYSA-N 3-benzyl-4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1CC1=CC=CC=C1 CWPBWQMSTGAQSS-UHFFFAOYSA-N 0.000 description 5
241000196324 Embryophyta Species 0.000 description 5
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
239000012141 concentrate Substances 0.000 description 5
238000001816 cooling Methods 0.000 description 5
GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 5
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
239000012188 paraffin wax Substances 0.000 description 5
239000011734 sodium Substances 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
DMHTVLQCVJYWSI-UHFFFAOYSA-N 1-methylcyclopropane-1-carbonitrile Chemical compound N#CC1(C)CC1 DMHTVLQCVJYWSI-UHFFFAOYSA-N 0.000 description 4
NWFCNKLMRINAEA-UHFFFAOYSA-N 2-[(4-bromo-2,3,5,6-tetrafluorophenyl)methoxy]oxane Chemical compound FC1=C(Br)C(F)=C(F)C(COC2OCCCC2)=C1F NWFCNKLMRINAEA-UHFFFAOYSA-N 0.000 description 4
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 4
241000257159 Musca domestica Species 0.000 description 4
240000007594 Oryza sativa Species 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
229910021529 ammonia Inorganic materials 0.000 description 4
235000019270 ammonium chloride Nutrition 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
238000004821 distillation Methods 0.000 description 4
PVTVLSHBNAMOCH-UHFFFAOYSA-N ethyl 4-(dimethylamino)-3-formyl-2-propan-2-ylbut-3-enoate Chemical compound CCOC(=O)C(C(C)C)C(C=O)=CN(C)C PVTVLSHBNAMOCH-UHFFFAOYSA-N 0.000 description 4
239000000417 fungicide Substances 0.000 description 4
239000004009 herbicide Substances 0.000 description 4
229910052744 lithium Inorganic materials 0.000 description 4
239000003921 oil Substances 0.000 description 4
235000019198 oils Nutrition 0.000 description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
239000007858 starting material Substances 0.000 description 4
JMXKSZRRTHPKDL-UHFFFAOYSA-N titanium ethoxide Chemical compound [Ti+4].CC[O-].CC[O-].CC[O-].CC[O-] JMXKSZRRTHPKDL-UHFFFAOYSA-N 0.000 description 4
VWXLCWNPSOUPPE-UHFFFAOYSA-N (1-amino-2-methylpropylidene)azanium;chloride Chemical compound Cl.CC(C)C(N)=N VWXLCWNPSOUPPE-UHFFFAOYSA-N 0.000 description 3
JQWYOABFEMFGKQ-UHFFFAOYSA-N (3-benzyl-4-fluorophenyl)methanol Chemical compound OCC1=CC=C(F)C(CC=2C=CC=CC=2)=C1 JQWYOABFEMFGKQ-UHFFFAOYSA-N 0.000 description 3
OWOHUVQVVSXZFR-UPHRSURJSA-N (z)-1-chloro-3-iodoprop-1-ene Chemical compound Cl\C=C/CI OWOHUVQVVSXZFR-UPHRSURJSA-N 0.000 description 3
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 description 3
HLCXNVMIINTAOG-UHFFFAOYSA-N 1-methylcyclopropane-1-carboxamide Chemical compound NC(=O)C1(C)CC1 HLCXNVMIINTAOG-UHFFFAOYSA-N 0.000 description 3
OSEGNECCBMDWRB-UHFFFAOYSA-N 2,2-dimethylbutanenitrile Chemical compound CCC(C)(C)C#N OSEGNECCBMDWRB-UHFFFAOYSA-N 0.000 description 3
ARDGQYVTLGUJII-UHFFFAOYSA-N 2,2-dimethylpropanimidamide;hydrochloride Chemical compound Cl.CC(C)(C)C(N)=N ARDGQYVTLGUJII-UHFFFAOYSA-N 0.000 description 3
OATOZCSPTSMOIY-UHFFFAOYSA-N 2-(3-bromo-4-fluorophenyl)-1,3-dioxolane Chemical compound C1=C(Br)C(F)=CC=C1C1OCCO1 OATOZCSPTSMOIY-UHFFFAOYSA-N 0.000 description 3
FAHZIKXYYRGSHF-UHFFFAOYSA-N 3-bromo-4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1Br FAHZIKXYYRGSHF-UHFFFAOYSA-N 0.000 description 3
239000005660 Abamectin Substances 0.000 description 3
241000238876 Acari Species 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
241000239290 Araneae Species 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
RAPBNVDSDCTNRC-UHFFFAOYSA-N Chlorobenzilate Chemical compound C=1C=C(Cl)C=CC=1C(O)(C(=O)OCC)C1=CC=C(Cl)C=C1 RAPBNVDSDCTNRC-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
238000004566 IR spectroscopy Methods 0.000 description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
241000255777 Lepidoptera Species 0.000 description 3
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
235000007164 Oryza sativa Nutrition 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
241001454293 Tetranychus urticae Species 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
PWLNAUNEAKQYLH-UHFFFAOYSA-N butyric acid octyl ester Natural products CCCCCCCCOC(=O)CCC PWLNAUNEAKQYLH-UHFFFAOYSA-N 0.000 description 3
230000003197 catalytic effect Effects 0.000 description 3
150000001805 chlorine compounds Chemical class 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
LHHLYOVYBZWIGM-UHFFFAOYSA-N diethyl 2-formylbutanedioate Chemical compound CCOC(=O)CC(C=O)C(=O)OCC LHHLYOVYBZWIGM-UHFFFAOYSA-N 0.000 description 3
239000002270 dispersing agent Substances 0.000 description 3
239000006185 dispersion Substances 0.000 description 3
239000003995 emulsifying agent Substances 0.000 description 3
BPEVJSLUAXMXTF-UHFFFAOYSA-N ethyl 2-(2-tert-butyl-6-oxo-1h-pyrimidin-5-yl)acetate Chemical compound CCOC(=O)CC1=CN=C(C(C)(C)C)NC1=O BPEVJSLUAXMXTF-UHFFFAOYSA-N 0.000 description 3
LJSXAPHAERLQBH-UHFFFAOYSA-N ethyl 2-(2-tert-butylpyrimidin-5-yl)acetate Chemical compound CCOC(=O)CC1=CN=C(C(C)(C)C)N=C1 LJSXAPHAERLQBH-UHFFFAOYSA-N 0.000 description 3
CZZHJCFFJKGLEV-UHFFFAOYSA-N ethyl 4-ethoxy-3-formyl-2-propan-2-ylbut-3-enoate Chemical compound CCOC=C(C=O)C(C(C)C)C(=O)OCC CZZHJCFFJKGLEV-UHFFFAOYSA-N 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
238000004508 fractional distillation Methods 0.000 description 3
239000007789 gas Substances 0.000 description 3
239000004615 ingredient Substances 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
MIGBWXJEXZFAMX-UHFFFAOYSA-N methyl 2,3,5-trifluoro-6-methoxy-4-(methoxymethyl)benzoate Chemical compound COCC1=C(F)C(F)=C(C(=O)OC)C(OC)=C1F MIGBWXJEXZFAMX-UHFFFAOYSA-N 0.000 description 3
UUIQMZJEGPQKFD-UHFFFAOYSA-N n-butyric acid methyl ester Natural products CCCC(=O)OC UUIQMZJEGPQKFD-UHFFFAOYSA-N 0.000 description 3
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
235000009566 rice Nutrition 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
239000002002 slurry Substances 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
238000003860 storage Methods 0.000 description 3
239000003039 volatile agent Substances 0.000 description 3
238000005406 washing Methods 0.000 description 3
238000009736 wetting Methods 0.000 description 3
239000000080 wetting agent Substances 0.000 description 3
FMCAFXHLMUOIGG-IWFBPKFRSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2r)-2-formamido-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,5-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoic acid Chemical compound O=CN[C@@H](CS)C(=O)N[C@@H](C(C)C)C(=O)N[C@H](C(=O)N[C@@H](CCSC)C(O)=O)CC1=CC(C)=C(O)C=C1C FMCAFXHLMUOIGG-IWFBPKFRSA-N 0.000 description 2
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150000003633 juvenile hormone derivatives 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
239000003350 kerosene Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000000787 lecithin Substances 0.000 description 1
235000010445 lecithin Nutrition 0.000 description 1
GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 1
229940040692 lithium hydroxide monohydrate Drugs 0.000 description 1
244000144972 livestock Species 0.000 description 1
150000004668 long chain fatty acids Chemical class 0.000 description 1
230000007774 longterm Effects 0.000 description 1
239000003120 macrolide antibiotic agent Substances 0.000 description 1
229940041033 macrolides Drugs 0.000 description 1
229960000453 malathion Drugs 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
NNKVPIKMPCQWCG-UHFFFAOYSA-N methamidophos Chemical compound COP(N)(=O)SC NNKVPIKMPCQWCG-UHFFFAOYSA-N 0.000 description 1
ITNVWQNWHXEMNS-UHFFFAOYSA-N methanolate;titanium(4+) Chemical compound [Ti+4].[O-]C.[O-]C.[O-]C.[O-]C ITNVWQNWHXEMNS-UHFFFAOYSA-N 0.000 description 1
229930002897 methoprene Natural products 0.000 description 1
229950003442 methoprene Drugs 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
AGJSNMGHAVDLRQ-HUUJSLGLSA-N methyl (2s)-2-[[(2r)-2-[[(2s)-2-[[(2r)-2-amino-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,3-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoate Chemical compound SC[C@H](N)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(=O)N[C@@H](CCSC)C(=O)OC)CC1=CC=C(O)C(C)=C1C AGJSNMGHAVDLRQ-HUUJSLGLSA-N 0.000 description 1
ZLBGSRMUSVULIE-GSMJGMFJSA-N milbemycin A3 Chemical class O1[C@H](C)[C@@H](C)CC[C@@]11O[C@H](C\C=C(C)\C[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 ZLBGSRMUSVULIE-GSMJGMFJSA-N 0.000 description 1
KRTSDMXIXPKRQR-AATRIKPKSA-N monocrotophos Chemical compound CNC(=O)\C=C(/C)OP(=O)(OC)OC KRTSDMXIXPKRQR-AATRIKPKSA-N 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 1
229940055577 oleyl alcohol Drugs 0.000 description 1
XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000003151 ovacidal effect Effects 0.000 description 1
KZAUOCCYDRDERY-UHFFFAOYSA-N oxamyl Chemical compound CNC(=O)ON=C(SC)C(=O)N(C)C KZAUOCCYDRDERY-UHFFFAOYSA-N 0.000 description 1
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
RLBIQVVOMOPOHC-UHFFFAOYSA-N parathion-methyl Chemical compound COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C=C1 RLBIQVVOMOPOHC-UHFFFAOYSA-N 0.000 description 1
125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
239000003444 phase transfer catalyst Substances 0.000 description 1
BULVZWIRKLYCBC-UHFFFAOYSA-N phorate Chemical compound CCOP(=S)(OCC)SCSCC BULVZWIRKLYCBC-UHFFFAOYSA-N 0.000 description 1
IOUNQDKNJZEDEP-UHFFFAOYSA-N phosalone Chemical compound C1=C(Cl)C=C2OC(=O)N(CSP(=S)(OCC)OCC)C2=C1 IOUNQDKNJZEDEP-UHFFFAOYSA-N 0.000 description 1
RGCLLPNLLBQHPF-HJWRWDBZSA-N phosphamidon Chemical compound CCN(CC)C(=O)C(\Cl)=C(/C)OP(=O)(OC)OC RGCLLPNLLBQHPF-HJWRWDBZSA-N 0.000 description 1
RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
ATROHALUCMTWTB-OWBHPGMISA-N phoxim Chemical compound CCOP(=S)(OCC)O\N=C(\C#N)C1=CC=CC=C1 ATROHALUCMTWTB-OWBHPGMISA-N 0.000 description 1
229950001664 phoxim Drugs 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
229960005235 piperonyl butoxide Drugs 0.000 description 1
YFGYUFNIOHWBOB-UHFFFAOYSA-N pirimicarb Chemical compound CN(C)C(=O)OC1=NC(N(C)C)=NC(C)=C1C YFGYUFNIOHWBOB-UHFFFAOYSA-N 0.000 description 1
QHOQHJPRIBSPCY-UHFFFAOYSA-N pirimiphos-methyl Chemical group CCN(CC)C1=NC(C)=CC(OP(=S)(OC)OC)=N1 QHOQHJPRIBSPCY-UHFFFAOYSA-N 0.000 description 1
JAMNHZBIQDNHMM-UHFFFAOYSA-N pivalonitrile Chemical compound CC(C)(C)C#N JAMNHZBIQDNHMM-UHFFFAOYSA-N 0.000 description 1
239000004033 plastic Substances 0.000 description 1
235000011056 potassium acetate Nutrition 0.000 description 1
235000003270 potassium fluoride Nutrition 0.000 description 1
239000000843 powder Substances 0.000 description 1
QYMMJNLHFKGANY-UHFFFAOYSA-N profenofos Chemical compound CCCSP(=O)(OCC)OC1=CC=C(Br)C=C1Cl QYMMJNLHFKGANY-UHFFFAOYSA-N 0.000 description 1
LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical group CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 description 1
ZYHMJXZULPZUED-UHFFFAOYSA-N propargite Chemical compound C1=CC(C(C)(C)C)=CC=C1OC1C(OS(=O)OCC#C)CCCC1 ZYHMJXZULPZUED-UHFFFAOYSA-N 0.000 description 1
LJZPPWWHKPGCHS-UHFFFAOYSA-N propargyl chloride Chemical compound ClCC#C LJZPPWWHKPGCHS-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000008262 pumice Substances 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
VJFUPGQZSXIULQ-XIGJTORUSA-N pyrethrin II Chemical compound CC1(C)[C@H](/C=C(\C)C(=O)OC)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 VJFUPGQZSXIULQ-XIGJTORUSA-N 0.000 description 1
AFHQSQTUSWXNCL-UHFFFAOYSA-N pyrimidin-5-ol Chemical compound OC1=CN=CN=C1.OC1=CN=CN=C1 AFHQSQTUSWXNCL-UHFFFAOYSA-N 0.000 description 1
NHDHVHZZCFYRSB-UHFFFAOYSA-N pyriproxyfen Chemical compound C=1C=CC=NC=1OC(C)COC(C=C1)=CC=C1OC1=CC=CC=C1 NHDHVHZZCFYRSB-UHFFFAOYSA-N 0.000 description 1
150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000008929 regeneration Effects 0.000 description 1
238000011069 regeneration method Methods 0.000 description 1
239000005871 repellent Substances 0.000 description 1
230000002940 repellent Effects 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000010956 selective crystallization Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000344 soap Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical class [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
229920005552 sodium lignosulfonate Polymers 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
239000002689 soil Substances 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000007921 spray Substances 0.000 description 1
125000005017 substituted alkenyl group Chemical group 0.000 description 1
JXHJNEJVUNHLKO-UHFFFAOYSA-N sulprofos Chemical compound CCCSP(=S)(OCC)OC1=CC=C(SC)C=C1 JXHJNEJVUNHLKO-UHFFFAOYSA-N 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
UOORRWUZONOOLO-UHFFFAOYSA-N telone II Natural products ClCC=CCl UOORRWUZONOOLO-UHFFFAOYSA-N 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
MLGCXEBRWGEOQX-UHFFFAOYSA-N tetradifon Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC(Cl)=C(Cl)C=C1Cl MLGCXEBRWGEOQX-UHFFFAOYSA-N 0.000 description 1
BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
229960005199 tetramethrin Drugs 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
OPASCBHCTNRLRM-UHFFFAOYSA-N thiometon Chemical compound CCSCCSP(=S)(OC)OC OPASCBHCTNRLRM-UHFFFAOYSA-N 0.000 description 1
150000003608 titanium Chemical class 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
GUANKKYBIGFNCV-UHFFFAOYSA-N trimethyl-[2,3,5,6-tetrafluoro-4-(oxan-2-yloxymethyl)phenyl]silane Chemical compound FC1=C(F)C([Si](C)(C)C)=C(F)C(F)=C1COC1OCCCC1 GUANKKYBIGFNCV-UHFFFAOYSA-N 0.000 description 1
239000002023 wood Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
- 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
- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/30—Halogen atoms or nitro radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Dentistry (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Agronomy & Crop Science (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

CS869701A 1985-12-23 1986-12-22 Insecticide and acaricide and method of active substances production CS269991B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB858531637A GB8531637D0 (en)	1985-12-23	1985-12-23	Pyrimidine derivatives

Publications (2)

Publication Number	Publication Date
CS970186A2 CS970186A2 (en)	1989-09-12
CS269991B2 true CS269991B2 (en)	1990-05-14

Family

ID=10590192

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS869701A CS269991B2 (en)	1985-12-23	1986-12-22	Insecticide and acaricide and method of active substances production

Country Status (17)

Country	Link
US (1)	US4762835A (pt)
EP (1)	EP0227415A3 (pt)
JP (1)	JPS62158262A (pt)
KR (1)	KR870006015A (pt)
CN (1)	CN1014061B (pt)
AP (1)	AP35A (pt)
AR (1)	AR242785A1 (pt)
AU (1)	AU604663B2 (pt)
BR (1)	BR8606428A (pt)
CA (1)	CA1269662A (pt)
CS (1)	CS269991B2 (pt)
GB (2)	GB8531637D0 (pt)
HU (2)	HU201529B (pt)
IL (1)	IL81016A (pt)
OA (1)	OA08565A (pt)
PT (1)	PT84010B (pt)
ZA (1)	ZA869480B (pt)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0162538A3 (en) *	1984-03-26	1986-10-29	Imperial Chemical Industries Plc	Cyclopropane derivates
US4962109A (en) *	1985-12-23	1990-10-09	Imperial Chemical Industries Plc	Insecticidally and acaricidally active pyrimidine esters and intermediates therefor
GB8714233D0 (en) *	1987-06-17	1987-07-22	Ici Plc	Pyrimidine derivatives
GB8626520D0 (en) *	1986-11-06	1986-12-10	Ici Plc	Halogenated esters
GB8629806D0 (en) *	1986-12-12	1987-01-21	Ici Plc	Fluorobenzyl esters
US5601098A (en) *	1995-06-02	1997-02-11	Dimon Incorporated	Method and apparatus for applying methoprene to oriental tobacco
US5932736A (en) *	1997-04-07	1999-08-03	Reilly Industries, Inc.	Preparation of heterocycles using 1,3-dihalopropenes
AR029489A1 (es) *	2000-03-10	2003-07-02	Euro Celtique Sa	Piridinas, pirimidinas, pirazinas, triazinas sustituidas por arilo, composiciones farmaceuticas y el uso de las mismas para la manufactura de un medicamento
AR037233A1 (es) *	2001-09-07	2004-11-03	Euro Celtique Sa	Piridinas aril sustituidas, composiciones farmaceuticas y el uso de dichos compuestos para la elaboracion de un medicamento
AU2002953128A0 (en) *	2002-12-05	2002-12-19	Osmose (Australia) Pty Ltd	Surface treatment for wood and wood products
US8293753B2 (en)	2009-07-02	2012-10-23	Novartis Ag	Substituted 2-carboxamide cycloamino ureas
WO2012150207A1 (de)	2011-05-04	2012-11-08	Bayer Cropscience Ag	Verwendung von cyclopropancarbonsäureeesterderivaten zur bekämpfung von insektizid-resistenten insekten
WO2012150206A2 (de)	2011-05-04	2012-11-08	Bayer Cropscience Ag	Neue cyclopropansäureeesterderivate als schädlingsbekämpfungsmittel
JP7220954B2 (ja) *	2019-06-07	2023-02-13	大日本除蟲菊株式会社	エステル化合物及びその用途
CN114605335A (zh) *	2022-04-11	2022-06-10	青岛科技大学	一种嘧啶硫醚胺酯类杀虫剂
JP7572591B2 (ja) *	2023-12-22	2024-10-23	住友化学株式会社	エステル化合物及びその用途
CN118339138B (zh) *	2023-12-22	2025-02-11	住友化学株式会社	酯化合物及其用途

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3887708A (en) *	1972-03-13	1975-06-03	Lilly Co Eli	Alpha, alpha-disubstituted-5-pyrimidinemethanes used as fungicides
EP0162538A3 (en) *	1984-03-26	1986-10-29	Imperial Chemical Industries Plc	Cyclopropane derivates

1985
- 1985-12-23 GB GB858531637A patent/GB8531637D0/en active Pending
1986
- 1986-12-16 EP EP86309808A patent/EP0227415A3/en not_active Ceased
- 1986-12-16 GB GB8630011A patent/GB2184441B/en not_active Expired - Lifetime
- 1986-12-16 US US06/942,436 patent/US4762835A/en not_active Expired - Fee Related
- 1986-12-17 ZA ZA869480A patent/ZA869480B/xx unknown
- 1986-12-18 CA CA000525745A patent/CA1269662A/en not_active Expired - Lifetime
- 1986-12-18 AP APAP/P/1986/000051A patent/AP35A/en active
- 1986-12-18 IL IL81016A patent/IL81016A/xx unknown
- 1986-12-19 AU AU66809/86A patent/AU604663B2/en not_active Ceased
- 1986-12-19 HU HU865339A patent/HU201529B/hu unknown
- 1986-12-19 HU HU904110A patent/HU206202B/hu not_active IP Right Cessation
- 1986-12-22 OA OA59029A patent/OA08565A/xx unknown
- 1986-12-22 CS CS869701A patent/CS269991B2/cs unknown
- 1986-12-23 PT PT84010A patent/PT84010B/pt not_active IP Right Cessation
- 1986-12-23 BR BR8606428A patent/BR8606428A/pt unknown
- 1986-12-23 AR AR86306315A patent/AR242785A1/es active
- 1986-12-23 JP JP61305568A patent/JPS62158262A/ja active Pending
- 1986-12-23 CN CN86108825A patent/CN1014061B/zh not_active Expired
- 1986-12-23 KR KR860011272A patent/KR870006015A/ko not_active Withdrawn

Also Published As

Publication number	Publication date
HU904110D0 (en)	1990-12-28
EP0227415A3 (en)	1988-03-23
PT84010B (pt)	1989-07-31
US4762835A (en)	1988-08-09
AU604663B2 (en)	1991-01-03
HUT42453A (en)	1987-07-28
PT84010A (en)	1987-01-01
AU6680986A (en)	1987-06-25
CN86108825A (zh)	1987-07-22
AR242785A1 (es)	1993-05-31
AP35A (en)	1989-02-15
BR8606428A (pt)	1987-10-20
KR870006015A (ko)	1987-07-08
CA1269662A (en)	1990-05-29
IL81016A0 (en)	1987-03-31
IL81016A (en)	1992-03-29
GB8630011D0 (en)	1987-01-28
HU206202B (en)	1992-09-28
HUT45290A (en)	1988-06-28
CS970186A2 (en)	1989-09-12
GB2184441B (en)	1990-05-09
GB8531637D0 (en)	1986-02-05
OA08565A (en)	1988-09-30
ZA869480B (en)	1987-08-26
HU201529B (en)	1990-11-28
JPS62158262A (ja)	1987-07-14
GB2184441A (en)	1987-06-24
EP0227415A2 (en)	1987-07-01
CN1014061B (zh)	1991-09-25
AP8600051A0 (en)	1986-11-01

Publication	Publication Date	Title
CS269991B2 (en)	1990-05-14	Insecticide and acaricide and method of active substances production
CA1276182C (en)	1990-11-13	Phenyl pyridones and thiopyridones
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