DD147196A5 - Insektizide mittel - Google Patents

Insektizide mittel Download PDF

Info

Publication number: DD147196A5
Authority: DD; German Democratic Republic
Prior art keywords: dimethyl; formula; spp; chloro; trifluoropropenyl
Prior art date: 1978-07-15

Application number

DD79214235A

Other languages

German (de)

English (en)

Inventor

Reinhard Lantzsch

Hermann Hagemann

Ingeborg Hammann

Wolfgang Behrenz

Bernhard Homeyer

Original Assignee

Bayer Ag

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.)

1978-07-15

Filing date

1979-07-10

Publication date

1981-03-25

1979-07-10 Application filed by Bayer Ag filed Critical Bayer Ag

1981-03-25 Publication of DD147196A5 publication Critical patent/DD147196A5/de

Links

239000002917 insecticide Substances 0.000 title description 3
239000000460 chlorine Chemical group 0.000 claims abstract description 22
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 13
229910052801 chlorine Inorganic materials 0.000 claims abstract description 9
239000011737 fluorine Substances 0.000 claims abstract description 9
229910052731 fluorine Inorganic materials 0.000 claims abstract description 9
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 8
125000001153 fluoro group Chemical group F* 0.000 claims abstract description 8
229910052794 bromium Inorganic materials 0.000 claims abstract description 7
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 6
-1 cyclopropanecarboxylic acid ester Chemical class 0.000 claims description 22
239000000203 mixture Substances 0.000 claims description 22
238000002360 preparation method Methods 0.000 claims description 21
238000000034 method Methods 0.000 claims description 15
241000238631 Hexapoda Species 0.000 claims description 9
YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 claims description 9
239000003795 chemical substances by application Substances 0.000 claims description 6
230000000749 insecticidal effect Effects 0.000 claims description 6
241000239223 Arachnida Species 0.000 claims description 5
239000004606 Fillers/Extenders Substances 0.000 claims description 3
230000000895 acaricidal effect Effects 0.000 claims description 3
VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 claims description 2
239000004094 surface-active agent Substances 0.000 claims description 2
150000001875 compounds Chemical class 0.000 abstract description 63
229910052736 halogen Inorganic materials 0.000 abstract description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 5
150000001336 alkenes Chemical class 0.000 abstract description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 abstract 1
229920002554 vinyl polymer Polymers 0.000 abstract 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
239000002904 solvent Substances 0.000 description 25
238000012360 testing method Methods 0.000 description 24
239000002253 acid Substances 0.000 description 20
238000006243 chemical reaction Methods 0.000 description 20
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
241001465754 Metazoa Species 0.000 description 13
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
239000000243 solution Substances 0.000 description 13
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
239000007858 starting material Substances 0.000 description 12
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 10
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
239000004480 active ingredient Substances 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
YMGUBTXCNDTFJI-UHFFFAOYSA-M cyclopropanecarboxylate Chemical compound [O-]C(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-M 0.000 description 9
239000003995 emulsifying agent Substances 0.000 description 9
238000009472 formulation Methods 0.000 description 9
229910052739 hydrogen Inorganic materials 0.000 description 9
150000003839 salts Chemical class 0.000 description 9
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
150000001298 alcohols Chemical class 0.000 description 7
WVDDGKGOMKODPV-UHFFFAOYSA-N benzyl alcohol Substances OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 7
239000003054 catalyst Substances 0.000 description 7
230000000694 effects Effects 0.000 description 7
229910052751 metal Inorganic materials 0.000 description 7
239000002184 metal Substances 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 6
229960004217 benzyl alcohol Drugs 0.000 description 6
239000001257 hydrogen Substances 0.000 description 6
239000002689 soil Substances 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
239000000370 acceptor Substances 0.000 description 5
239000002585 base Substances 0.000 description 5
239000003085 diluting agent Substances 0.000 description 5
239000008187 granular material Substances 0.000 description 5
150000004820 halides Chemical class 0.000 description 5
150000002367 halogens Chemical class 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
150000003242 quaternary ammonium salts Chemical class 0.000 description 5
101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 description 4
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
239000013543 active substance Substances 0.000 description 4
125000002877 alkyl aryl group Chemical group 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
239000000969 carrier Substances 0.000 description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
239000007788 liquid Substances 0.000 description 4
239000003444 phase transfer catalyst Substances 0.000 description 4
229920000151 polyglycol Polymers 0.000 description 4
239000010695 polyglycol Substances 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
238000007127 saponification reaction Methods 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
SPVZAYWHHVLPBN-INEUFUBQSA-N (1s,3s)-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)[C@H](C=C(Cl)C(F)(F)F)[C@@H]1C(O)=O SPVZAYWHHVLPBN-INEUFUBQSA-N 0.000 description 3
KGANAERDZBAECK-UHFFFAOYSA-N (3-phenoxyphenyl)methanol Chemical compound OCC1=CC=CC(OC=2C=CC=CC=2)=C1 KGANAERDZBAECK-UHFFFAOYSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
241000251730 Chondrichthyes Species 0.000 description 3
241000254173 Coleoptera Species 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
244000028419 Styrax benzoin Species 0.000 description 3
235000000126 Styrax benzoin Nutrition 0.000 description 3
235000008411 Sumatra benzointree Nutrition 0.000 description 3
241000607479 Yersinia pestis Species 0.000 description 3
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
229960002130 benzoin Drugs 0.000 description 3
238000009835 boiling Methods 0.000 description 3
239000012141 concentrate Substances 0.000 description 3
238000006704 dehydrohalogenation reaction Methods 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
238000004821 distillation Methods 0.000 description 3
229940079593 drug Drugs 0.000 description 3
239000003814 drug Substances 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
238000000605 extraction Methods 0.000 description 3
235000019382 gum benzoic Nutrition 0.000 description 3
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
229910000041 hydrogen chloride Inorganic materials 0.000 description 3
125000000896 monocarboxylic acid group Chemical group 0.000 description 3
150000002825 nitriles Chemical class 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000008096 xylene Substances 0.000 description 3
ABALMDTULZCSTP-UJURSFKZSA-N (1s,3s)-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropane-1-carbonyl chloride Chemical compound CC1(C)[C@@H](C=C(Cl)C(F)(F)F)[C@@H]1C(Cl)=O ABALMDTULZCSTP-UJURSFKZSA-N 0.000 description 2
BOSAWIQFTJIYIS-UHFFFAOYSA-N 1,1,1-trichloro-2,2,2-trifluoroethane Chemical compound FC(F)(F)C(Cl)(Cl)Cl BOSAWIQFTJIYIS-UHFFFAOYSA-N 0.000 description 2
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
ABALMDTULZCSTP-UHFFFAOYSA-N 3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropane-1-carbonyl chloride Chemical compound CC1(C)C(C=C(Cl)C(F)(F)F)C1C(Cl)=O ABALMDTULZCSTP-UHFFFAOYSA-N 0.000 description 2
MRLGCTNJRREZHZ-UHFFFAOYSA-N 3-phenoxybenzaldehyde Chemical compound O=CC1=CC=CC(OC=2C=CC=CC=2)=C1 MRLGCTNJRREZHZ-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
241001143309 Acanthoscelides obtectus Species 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
241000238662 Blatta orientalis Species 0.000 description 2
240000007124 Brassica oleracea Species 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
241000255925 Diptera Species 0.000 description 2
241000196324 Embryophyta Species 0.000 description 2
241000258937 Hemiptera Species 0.000 description 2
241000257303 Hymenoptera Species 0.000 description 2
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 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical class [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
241001608567 Phaedon cochleariae Species 0.000 description 2
244000046052 Phaseolus vulgaris Species 0.000 description 2
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
241001481703 Rhipicephalus <genus> Species 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
241000254109 Tenebrio molitor Species 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
241001454295 Tetranychidae Species 0.000 description 2
241001454294 Tetranychus Species 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
239000003513 alkali Substances 0.000 description 2
229910001854 alkali hydroxide Inorganic materials 0.000 description 2
150000008044 alkali metal hydroxides Chemical class 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
150000001805 chlorine compounds Chemical class 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
239000013256 coordination polymer Substances 0.000 description 2
229910052802 copper Inorganic materials 0.000 description 2
239000010949 copper Substances 0.000 description 2
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
238000011161 development Methods 0.000 description 2
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
238000007598 dipping method Methods 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
239000000975 dye Substances 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
230000002349 favourable effect Effects 0.000 description 2
239000006260 foam Substances 0.000 description 2
239000003502 gasoline Substances 0.000 description 2
239000011521 glass Substances 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
230000002140 halogenating effect Effects 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
JGJLWPGRMCADHB-UHFFFAOYSA-N hypobromite Chemical compound Br[O-] JGJLWPGRMCADHB-UHFFFAOYSA-N 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
MKLKDUHMZCIBSJ-UHFFFAOYSA-N methyl 3,3-dimethylpent-4-enoate Chemical compound COC(=O)CC(C)(C)C=C MKLKDUHMZCIBSJ-UHFFFAOYSA-N 0.000 description 2
150000004702 methyl esters Chemical class 0.000 description 2
235000010755 mineral Nutrition 0.000 description 2
239000011707 mineral Substances 0.000 description 2
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
239000012071 phase Substances 0.000 description 2
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
238000002390 rotary evaporation Methods 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000000126 substance Substances 0.000 description 2
NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
ABALMDTULZCSTP-INEUFUBQSA-N (1s,3r)-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropane-1-carbonyl chloride Chemical compound CC1(C)[C@H](C=C(Cl)C(F)(F)F)[C@@H]1C(Cl)=O ABALMDTULZCSTP-INEUFUBQSA-N 0.000 description 1
SPVZAYWHHVLPBN-UJURSFKZSA-N (1s,3r)-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)[C@@H](C=C(Cl)C(F)(F)F)[C@@H]1C(O)=O SPVZAYWHHVLPBN-UJURSFKZSA-N 0.000 description 1
RWQIUNYZFAUGLQ-UHFFFAOYSA-N (2-chloro-3,3,3-trifluoroprop-1-enyl) cyclopropanecarboxylate Chemical compound ClC(=COC(=O)C1CC1)C(F)(F)F RWQIUNYZFAUGLQ-UHFFFAOYSA-N 0.000 description 1
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125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
229940043279 diisopropylamine Drugs 0.000 description 1
XHFGWHUWQXTGAT-UHFFFAOYSA-N dimethylamine hydrochloride Natural products CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 1
IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 1
XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
239000010459 dolomite Substances 0.000 description 1
229910000514 dolomite Inorganic materials 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
230000012173 estrus Effects 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
229940032296 ferric chloride Drugs 0.000 description 1
229960002089 ferrous chloride Drugs 0.000 description 1
235000013312 flour Nutrition 0.000 description 1
238000004508 fractional distillation Methods 0.000 description 1
239000011953 free-radical catalyst Substances 0.000 description 1
239000000446 fuel Substances 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
239000007789 gas Substances 0.000 description 1
238000003197 gene knockdown Methods 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
150000002366 halogen compounds Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
239000001023 inorganic pigment Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 1
229910000358 iron sulfate Inorganic materials 0.000 description 1
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
PVFSDGKDKFSOTB-UHFFFAOYSA-K iron(3+);triacetate Chemical compound [Fe+3].CC([O-])=O.CC([O-])=O.CC([O-])=O PVFSDGKDKFSOTB-UHFFFAOYSA-K 0.000 description 1
LZKLAOYSENRNKR-LNTINUHCSA-N iron;(z)-4-oxoniumylidenepent-2-en-2-olate Chemical compound [Fe].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O LZKLAOYSENRNKR-LNTINUHCSA-N 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical class [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000004579 marble Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
BYSHKFOMCYGXLU-UHFFFAOYSA-N methyl 3-(2-bromo-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound COC(=O)C1C(C=C(Br)C(F)(F)F)C1(C)C BYSHKFOMCYGXLU-UHFFFAOYSA-N 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 1
239000003595 mist Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
229910052750 molybdenum Inorganic materials 0.000 description 1
239000011733 molybdenum Substances 0.000 description 1
229910052901 montmorillonite Inorganic materials 0.000 description 1
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
125000002560 nitrile group Chemical group 0.000 description 1
JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
239000003921 oil Substances 0.000 description 1
239000011368 organic material Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
229910052625 palygorskite Inorganic materials 0.000 description 1
239000006072 paste Substances 0.000 description 1
150000004714 phosphonium salts Chemical class 0.000 description 1
239000001007 phthalocyanine dye Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
239000011118 polyvinyl acetate Substances 0.000 description 1
229920002689 polyvinyl acetate Polymers 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
SATVIFGJTRRDQU-UHFFFAOYSA-N potassium hypochlorite Chemical compound [K+].Cl[O-] SATVIFGJTRRDQU-UHFFFAOYSA-N 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
ORQYPOUSZINNCB-UHFFFAOYSA-N potassium;hypobromite Chemical compound [K+].Br[O-] ORQYPOUSZINNCB-UHFFFAOYSA-N 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000003825 pressing Methods 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
239000001294 propane Substances 0.000 description 1
239000003380 propellant Substances 0.000 description 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
239000003531 protein hydrolysate Substances 0.000 description 1
239000008262 pumice Substances 0.000 description 1
239000010453 quartz Substances 0.000 description 1
239000011435 rock Substances 0.000 description 1
LMHHRCOWPQNFTF-UHFFFAOYSA-N s-propan-2-yl azepane-1-carbothioate Chemical compound CC(C)SC(=O)N1CCCCCC1 LMHHRCOWPQNFTF-UHFFFAOYSA-N 0.000 description 1
238000009738 saturating Methods 0.000 description 1
229910052624 sepiolite Inorganic materials 0.000 description 1
235000019355 sepiolite Nutrition 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000000779 smoke Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
CRWJEUDFKNYSBX-UHFFFAOYSA-N sodium;hypobromite Chemical compound [Na+].Br[O-] CRWJEUDFKNYSBX-UHFFFAOYSA-N 0.000 description 1
241000894007 species Species 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000004544 spot-on Substances 0.000 description 1
238000005507 spraying Methods 0.000 description 1
238000003860 storage Methods 0.000 description 1
125000003107 substituted aryl group Chemical group 0.000 description 1
239000000758 substrate Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
239000002023 wood Substances 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/69—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to carbon-to-carbon double or triple bonds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/16—Saturated compounds containing keto groups bound to acyclic carbon atoms containing halogen
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
- C07C51/60—Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Oil, Petroleum & Natural Gas (AREA)
Dentistry (AREA)
Environmental Sciences (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Agronomy & Crop Science (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Furan Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Indole Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Catching Or Destruction (AREA)

DD79214235A 1978-07-15 1979-07-10 Insektizide mittel DD147196A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19782831193 DE2831193A1 (de)	1978-07-15	1978-07-15	Fluoralkenylsubstituierte cyclopropancarbonsaeureester und ihre verwendung als insektizide

Publications (1)

Publication Number	Publication Date
DD147196A5 true DD147196A5 (de)	1981-03-25

Family

ID=6044499

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD79214235A DD147196A5 (de)	1978-07-15	1979-07-10	Insektizide mittel

Country Status (20)

Country	Link
US (1)	US4252820A (fr)
EP (1)	EP0008340B1 (fr)
JP (1)	JPS5589248A (fr)
AT (1)	ATE5649T1 (fr)
AU (1)	AU531358B2 (fr)
BG (1)	BG30316A3 (fr)
BR (1)	BR7904488A (fr)
CS (1)	CS209816B2 (fr)
DD (1)	DD147196A5 (fr)
DE (2)	DE2831193A1 (fr)
DK (1)	DK296279A (fr)
EG (1)	EG13727A (fr)
ES (1)	ES482461A0 (fr)
HU (1)	HU182926B (fr)
IL (1)	IL57777A (fr)
PL (1)	PL120130B1 (fr)
PT (1)	PT69893A (fr)
RO (1)	RO78862A (fr)
TR (1)	TR20983A (fr)
ZA (1)	ZA793548B (fr)

Families Citing this family (36)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4378316A (en) *	1977-01-24	1983-03-29	Imperial Chemical Industries Limited	Halogenated esters
ZA795532B (en) *	1978-10-27	1980-09-24	Ici Ltd	Halogenated esters of cyclopropane acids,their preparation compositions and use as pesticides
DE2964152D1 (en) *	1978-10-31	1983-01-05	Ici Plc	Process for the preparation of cyclopropane carboxylic acid esters
DE3060562D1 (en) *	1979-02-14	1982-08-12	Ici Plc	Esters of halogenated substituted cyclopropanoic acids, their preparation and use as insecticides
US4332815A (en) *	1979-06-25	1982-06-01	Fmc Corporation	Insecticidal perhaloalkylvinylcyclopropanecarboxylates
US4370346A (en) *	1979-12-21	1983-01-25	Imperial Chemical Industries Plc	Halogenated esters
DE3065914D1 (en) *	1979-12-21	1984-01-19	Ici Plc	Substituted benzyl esters of cyclopropane carboxylic acids and their preparation, compositions containing them and methods of combating insect pests therewith, and substituted benzyl alcohols
DE3019552A1 (de) *	1980-05-22	1981-11-26	Bayer Ag, 5090 Leverkusen	3-(2-chlor-3,3,4,4,4-pentafluor-1-butenyl)-2,2-dimethyl-cyclopropancarbonsaeureester, verfahren zu deren herstellung und deren verwendung in schaedlingsbekaempfungsmitteln
IT1131883B (it) *	1980-07-02	1986-06-25	Montedison Spa	Processo per la sintesi stereoselettiva di ciclopropancarbossilati intermaedi per piretroidi
US4375476A (en) *	1980-10-14	1983-03-01	Fmc Corporation	Insecticidal (2,6-dimethyl-3-substituted phenyl)methyl cyclopropanecarboxylates
EP0050776B1 (fr) *	1980-10-23	1983-11-16	Bayer Ag	Procédé de préparation d'esters de l'acide cyclopropancarboxylique substitués par un groupe chloro-fluoroalcényle
DE3100354A1 (de) *	1981-01-08	1982-08-05	Bayer Ag, 5090 Leverkusen	Verfahren zur herstellung von 2,2-dimethyl-3-vinyl-cyclopropancarbonsaeuren und deren estern
EP0057795B1 (fr) *	1981-01-21	1985-07-10	Imperial Chemical Industries Plc	Esters halobenzyliques d'acides haloalkénylcyclopropaniques, leurs préparations, leurs compositions et applications comme pesticides
ZA8295B (en) *	1981-01-21	1982-11-24	Ici Plc	Halobenzyl esters
US4415748A (en) *	1981-08-06	1983-11-15	Fmc Corporation	Intermediates for insecticidal synthetic pyrethroids
EP0073566A1 (fr) *	1981-08-27	1983-03-09	Imperial Chemical Industries Plc	Procédés et compositions pour combattre les pestes dans la terre
EP0091208B1 (fr) *	1982-04-05	1986-06-18	Imperial Chemical Industries Plc	Méthode pour la lutte contre les insectes et cyclopropanecarboxylates utilisables comme composés actifs dans celle-ci
US4778822A (en) *	1982-05-21	1988-10-18	Imperial Chemical Industries Plc	Insecticidally active ester
US4758590A (en) *	1984-03-14	1988-07-19	Fmc Corporation	Method for control of soil-borne insects
GB8418331D0 (en) *	1984-07-18	1984-08-22	Ici Plc	Insecticidal ester
JPS6168458A (ja) *	1984-09-12	1986-04-08	Sumitomo Chem Co Ltd	α−シアノベンジルエステルの製造方法
DE3513978A1 (de) *	1985-04-18	1986-10-30	Bayer Ag, 5090 Leverkusen	Vinylcyclopropancarbonsaeureester
EP0197115A4 (fr) *	1984-10-10	1989-08-29	Fmc Corp	Procede d'elimination d'insectes vivant dans le sol.
PH21875A (en) *	1985-04-26	1988-03-25	Sumitomo Chemical Co	Novel carboxylic acid esters,their method of use and insecticides containing them as the active ingredient
JPH0674238B2 (ja) *	1985-09-30	1994-09-21	財団法人相模中央化学研究所	２，２−ジメチルシクロプロパンカルボン酸誘導体
AU615879B2 (en) *	1986-08-27	1991-10-17	Montedison S.P.A.	Derivatives of 2,2-dimethyl-cyclopropanecarboxylic acid
GB8626520D0 (en) *	1986-11-06	1986-12-10	Ici Plc	Halogenated esters
US5238957A (en) *	1988-07-07	1993-08-24	Presidenza Del Consiglio Dei Ministri-Uffico Del Ministro Per Il Coordinamento Delle Iniziative Per La Ricerca Scientifica E Tecnologica	Esters of 2,2-dimethyl-cyclopropane-carboxylic acid
GB9100654D0 (en) *	1991-01-11	1991-02-27	Ici Plc	Process for preparing halogenated compounds
FR2687666A1 (fr) *	1992-02-21	1993-08-27	Roussel Uclaf	Nouveaux esters pyrethrinouiques, derives de l'alcool 6-(trifluoromethyl) benzylique, leur procede de preparation et leur application comme pesticides.
FR2708600B1 (fr) *	1993-08-05	1995-09-15	Roussel Uclaf	Nouveaux dérivés de l'alcool 6-trifluorométhyl benzylique, leur procédé de préparation et leur application comme pesticides.
GB0130517D0 (en) *	2001-12-20	2002-02-06	Syngenta Ltd	Chemical process
GB0304132D0 (en) *	2003-02-24	2003-03-26	Syngenta Ltd	Chemical process
CN103242196B (zh) *	2013-05-15	2016-01-27	联保作物科技有限公司	环丙烷羧酸酯类化合物、其制备方法及其应用
CN103232367B (zh) *	2013-05-15	2015-02-25	联保作物科技有限公司	拟除虫菊酯类化合物、其制备方法及其应用
CN112028772B (zh) *	2020-09-23	2021-09-28	江苏春江润田农化有限公司	一种4,6,6-三氯-7,7,7-三氟-3,3-二甲基庚酸甲酯制备方法

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4183948A (en) *	1977-01-24	1980-01-15	Imperial Chemical Industries Limited	Halogenated esters
BE853137A (fr)	1977-03-31	1977-07-18	Faco Sa	Enrouleur a cordon electrique refractable
GB1572669A (en) *	1977-05-26	1980-08-28	Ici Ltd	Manufacture of esters
IN150399B (fr) *	1978-01-20	1982-09-25	Fmc Corp
BG48333A3 (en) *	1978-02-28	1991-01-15	Montedison Spa	Method for preparing of 2, 2- dimethyl cyclopropane carbonic acid derivatives

1978
- 1978-07-15 DE DE19782831193 patent/DE2831193A1/de not_active Withdrawn
1979
- 1979-07-02 AT AT79102223T patent/ATE5649T1/de not_active IP Right Cessation
- 1979-07-02 US US06/053,676 patent/US4252820A/en not_active Expired - Lifetime
- 1979-07-02 DE DE7979102223T patent/DE2966494D1/de not_active Expired
- 1979-07-02 EP EP79102223A patent/EP0008340B1/fr not_active Expired
- 1979-07-06 AU AU48732/79A patent/AU531358B2/en not_active Withdrawn - After Issue
- 1979-07-06 PT PT69893A patent/PT69893A/pt unknown
- 1979-07-10 BG BG044266A patent/BG30316A3/xx unknown
- 1979-07-10 DD DD79214235A patent/DD147196A5/de unknown
- 1979-07-12 IL IL57777A patent/IL57777A/xx not_active IP Right Cessation
- 1979-07-12 TR TR20983A patent/TR20983A/xx unknown
- 1979-07-13 JP JP8836279A patent/JPS5589248A/ja active Granted
- 1979-07-13 BR BR7904488A patent/BR7904488A/pt unknown
- 1979-07-13 HU HU79BA3813A patent/HU182926B/hu not_active IP Right Cessation
- 1979-07-13 DK DK296279A patent/DK296279A/da not_active Application Discontinuation
- 1979-07-13 ZA ZA00793548A patent/ZA793548B/xx unknown
- 1979-07-13 ES ES482461A patent/ES482461A0/es active Granted
- 1979-07-13 CS CS794927A patent/CS209816B2/cs unknown
- 1979-07-14 RO RO7998160A patent/RO78862A/fr unknown
- 1979-07-14 PL PL1979217119A patent/PL120130B1/pl unknown
- 1979-07-15 EG EG428/79A patent/EG13727A/xx active

Also Published As

Publication number	Publication date
ZA793548B (en)	1980-08-27
AU4873279A (en)	1980-01-24
JPS6312041B2 (fr)	1988-03-17
EG13727A (en)	1982-06-30
US4252820A (en)	1981-02-24
IL57777A (en)	1985-05-31
PL217119A1 (fr)	1980-08-11
ES8107148A1 (es)	1980-12-01
DK296279A (da)	1980-01-16
EP0008340A1 (fr)	1980-03-05
JPS5589248A (en)	1980-07-05
PL120130B1 (en)	1982-02-27
BR7904488A (pt)	1980-04-08
BG30316A3 (en)	1981-05-15
TR20983A (tr)	1983-03-22
IL57777A0 (en)	1979-11-30
AU531358B2 (en)	1983-08-18
EP0008340B1 (fr)	1983-12-21
HU182926B (en)	1984-03-28
ES482461A0 (es)	1980-12-01
DE2966494D1 (en)	1984-01-26
RO78862A (fr)	1982-07-06
ATE5649T1 (de)	1984-01-15
CS209816B2 (en)	1981-12-31
DE2831193A1 (de)	1980-01-24
PT69893A (en)	1979-08-01

Publication	Publication Date	Title
EP0008340B1 (fr)	1983-12-21	Esters d'acide cyclopropane carboxylique substitué par fluoroalcényl, produits intermédiaires, préparation des composés et leur utilisation comme insecticides et/ou acaricides
EP0019787B1 (fr)	1984-03-14	Esters d'acides 2-phénylalcén-1-yl-cyclopropane carboxyliques, procédé pour leur préparation et application comme insecticides et acaricides; intermédiaires pour leur préparation
EP0007576B1 (fr)	1983-11-16	Esters de dérivés du stilbène, procédé pour leur préparation, alcools de dérivés du stilbène comme produits intermédiaires, utilisation des esters comme insecticides
DD140194A5 (de)	1980-02-20	Insektizide und akarizide mittel
EP0121847B1 (fr)	1987-01-14	Esters d'acides 2,2-diméthyl-3-(2-halovinyl)-cyclopropanecarboxyliques, procédé pour leur préparation et leur utilisation comme pesticides
EP0033160B1 (fr)	1985-05-02	Esters substitués d'acide 3-(1,2-dibromo-alkyl)-2,2-diméthyl-cyclopropan-1-carboxylique, procédé et produits intermédiaires pour leur préparation et leur utilisation comme insecticides
EP0019090B1 (fr)	1983-05-18	Dérivés substitués de l'acide styrylcyclopropanecarboxylique, procédé pour leur préparation, leur utilisation, insecticides et acaricides, leur fabrication et procédé pour combattre les insectes
DD146537A5 (de)	1981-02-18	Insektizide und akarizide mittel
EP0057384B1 (fr)	1984-07-25	Esters 4-fluoro-3-halophénoxy benzyles, procédé pour leur fabrication et leur utilisation en pesticides ainsi que produits intermédiaires et procédé pour leur préparation
DE3513978A1 (de)	1986-10-30	Vinylcyclopropancarbonsaeureester
EP0026437B1 (fr)	1983-06-08	Esters fluorobenzyliques d'acide 3-(2,3-dichloro-3,3-difluoro-prop-1-én-1-yl)-2,2 diméthyl cyclopropane-carboxylique, procédé pour leur préparation et leur utilisation comme pesticides
EP0040742B1 (fr)	1983-07-13	Esters de l'acide 3-(chloro-3,3,4,4,4-pentafluoro-1-butényl)-2,2-diméthylcyclopropane carboxylique, procédé pour leur préparation et leur utilisation dans des insecticides
DE2842541A1 (de)	1980-05-22	Fluoralkenylsubstituierte cyclopropancarbonsaeureester und ihre verwendung als insektizide
EP0075146B1 (fr)	1985-10-23	Esters benzyliques contenant des groupes éther fluorés, procédé pour leur préparation et leur utilisation à titre d'insecticides
DE3005722A1 (de)	1981-08-20	Trifluormethylbenzylester, verfahren zu deren herstellung und deren verwendung in schaedlingsbekaempfungsmitteln
EP0020954A1 (fr)	1981-01-07	Esters fluorés d'acides oxyalcénylcyclopropanecarboxyliques, procédé pour leur préparation, produits intermédiaires, leur préparation, insecticides et acaricides contenant les produits finals, leur préparation et leur utilisation
DE3140092A1 (de)	1983-04-21	Substituierte vinylcyclopropancarbonsaeure-(6-phenoxy-2-pyridinyl)-methylester, verfahren zu ihrer herstellung sowie ihre verwendung als schaedlingsbekaempfungsmittel
DE2842542A1 (de)	1980-04-17	Substituierte bromostyryl-cyclopropancarbonsaeurephenoxybenzylester, verfahren zu ihrer herstellunnd ihre verwendung als insektizide und akarizide
DE2837524A1 (de)	1980-03-20	Substituierte alpha-phenyl-carbonsaeure- (4-fluoro-3-phenoxy-benzyl)-ester, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide
EP0095636A1 (fr)	1983-12-07	Iminoesters N-substitués, procédé de préparation et utilisation comme insecticide
DE2939661A1 (de)	1981-04-23	Substituierte (alpha)-phenyl-carbonsaeure-(3-phenoxy-benzyl)-ester, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide
DE2844816A1 (de)	1980-04-24	Fluorhaltige phenylessigsaeureester, verfahren zu deren herstellung, deren verwendung als insektizide und akarizide und zwischenprodukte zu deren herstellung
EP0084328A2 (fr)	1983-07-27	Esters d'acides cyclopropanecarboxyliques substitués par halogénure d'alcoyle, procédé de leur préparation et leur utilisation en tant qu'insecticides
DE3222910A1 (de)	1983-12-22	Allenyl-benzylester, verfahren zu ihrer herstellung sowie ihre verwendung zur schaedlingsbekaempfung