PL135350B1 - Method of obtaining novel pyretroides and insecticide and/or acaricide - Google Patents

Method of obtaining novel pyretroides and insecticide and/or acaricide Download PDF

Info

Publication number: PL135350B1
Authority: PL; Poland
Prior art keywords: formula; coor; model; group; coo
Prior art date: 1978-02-28

Application number

PL1979213760A

Other languages

English (en)

Polish (pl)

Other versions

PL213760A1 (pl

Original Assignee

Montedison Spa

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.)

1978-02-28

Filing date

1979-02-27

Publication date

1985-10-31

1978-02-28 Priority claimed from IT20713/78A external-priority patent/IT1095449B/it

1978-02-28 Priority claimed from IT2071478A external-priority patent/IT1095450B/it

1978-12-27 Priority claimed from IT3131078A external-priority patent/IT1160403B/it

1979-01-30 Priority claimed from IT1970379A external-priority patent/IT1166603B/it

1979-02-27 Application filed by Montedison Spa filed Critical Montedison Spa

1979-12-17 Publication of PL213760A1 publication Critical patent/PL213760A1/xx

1985-10-31 Publication of PL135350B1 publication Critical patent/PL135350B1/pl

Links

238000000034 method Methods 0.000 title claims description 28
230000000895 acaricidal effect Effects 0.000 title claims description 17
239000002917 insecticide Substances 0.000 title claims description 10
239000000642 acaricide Substances 0.000 title claims description 7
150000001875 compounds Chemical class 0.000 claims description 96
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 58
238000006243 chemical reaction Methods 0.000 claims description 33
239000000460 chlorine Substances 0.000 claims description 25
DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 claims description 20
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 16
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
229910052801 chlorine Inorganic materials 0.000 claims description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
125000001153 fluoro group Chemical group F* 0.000 claims description 10
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
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125000001246 bromo group Chemical group Br* 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 6
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VXSIXFKKSNGRRO-MXOVTSAMSA-N [(1s)-2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate;[(1s)-2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-3-[(e)-3-methoxy-2-methyl-3-oxoprop-1-enyl Chemical class CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1.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 VXSIXFKKSNGRRO-MXOVTSAMSA-N 0.000 description 5
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238000002360 preparation method Methods 0.000 description 5
HYJYGLGUBUDSLJ-UHFFFAOYSA-N pyrethrin Natural products CCC(=O)OC1CC(=C)C2CC3OC3(C)C2C2OC(=O)C(=C)C12 HYJYGLGUBUDSLJ-UHFFFAOYSA-N 0.000 description 5
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238000003786 synthesis reaction Methods 0.000 description 4
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
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LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical group C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 3
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
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125000005843 halogen group Chemical group 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
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SBNFWQZLDJGRLK-RTWAWAEBSA-N (1R)-trans-phenothrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 SBNFWQZLDJGRLK-RTWAWAEBSA-N 0.000 description 2
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HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
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150000001805 chlorine compounds Chemical class 0.000 description 1
239000003245 coal Substances 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
229940125773 compound 10 Drugs 0.000 description 1
229940125797 compound 12 Drugs 0.000 description 1
229940126543 compound 14 Drugs 0.000 description 1
229940125782 compound 2 Drugs 0.000 description 1
239000013068 control sample Substances 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
ZOOSILUVXHVRJE-UHFFFAOYSA-N cyclopropanecarbonyl chloride Chemical compound ClC(=O)C1CC1 ZOOSILUVXHVRJE-UHFFFAOYSA-N 0.000 description 1
229960005424 cypermethrin Drugs 0.000 description 1
KAATUXNTWXVJKI-UHFFFAOYSA-N cypermethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-UHFFFAOYSA-N 0.000 description 1
229960002483 decamethrin Drugs 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
238000011161 development Methods 0.000 description 1
LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
YYJNOYZRYGDPNH-MFKUBSTISA-N fenpyroximate Chemical compound C=1C=C(C(=O)OC(C)(C)C)C=CC=1CO/N=C/C=1C(C)=NN(C)C=1OC1=CC=CC=C1 YYJNOYZRYGDPNH-MFKUBSTISA-N 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000000806 fluorine-19 nuclear magnetic resonance spectrum Methods 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
230000000977 initiatory effect Effects 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
231100000636 lethal dose Toxicity 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
TWXDDNPPQUTEOV-FVGYRXGTSA-N methamphetamine hydrochloride Chemical group Cl.CN[C@@H](C)CC1=CC=CC=C1 TWXDDNPPQUTEOV-FVGYRXGTSA-N 0.000 description 1
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000008188 pellet Substances 0.000 description 1
229960000490 permethrin Drugs 0.000 description 1
RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
230000002688 persistence Effects 0.000 description 1
231100000572 poisoning Toxicity 0.000 description 1
230000000607 poisoning effect Effects 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
230000008569 process Effects 0.000 description 1
238000012545 processing Methods 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
ROVGZAWFACYCSP-VUMXUWRFSA-N pyrethrin I Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 ROVGZAWFACYCSP-VUMXUWRFSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000006462 rearrangement reaction Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000005507 spraying Methods 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
239000000725 suspension Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
239000008399 tap water Substances 0.000 description 1
235000020679 tap water Nutrition 0.000 description 1
229960005199 tetramethrin Drugs 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
230000007704 transition Effects 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
230000000007 visual effect Effects 0.000 description 1
239000000080 wetting agent Substances 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C61/16—Unsaturated compounds
- C07C61/40—Unsaturated compounds containing halogen

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Wood Science & Technology (AREA)
Environmental Sciences (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Agronomy & Crop Science (AREA)
Zoology (AREA)
Pest Control & Pesticides (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Indole Compounds (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Furan Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

PL1979213760A 1978-02-28 1979-02-27 Method of obtaining novel pyretroides and insecticide and/or acaricide PL135350B1 (pl)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
IT20713/78A IT1095449B (it)	1978-02-28	1978-02-28	Nuovi piretroidi
IT2071478A IT1095450B (it)	1978-02-28	1978-02-28	Nuovi acidi ed esteri ciclopropancarbossilici
IT3131078A IT1160403B (it)	1978-12-27	1978-12-27	Processo per la sintesi di acidi ed esteri ciclopropancarbossilici
IT1970379A IT1166603B (it)	1979-01-30	1979-01-30	Piretroidi

Publications (2)

Publication Number	Publication Date
PL213760A1 PL213760A1 (pl)	1979-12-17
PL135350B1 true PL135350B1 (pl)	1985-10-31

Family

ID=27452781

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
PL1979213760A PL135350B1 (pl)	1978-02-28	1979-02-27	Method of obtaining novel pyretroides and insecticide and/or acaricide

Country Status (28)

Country	Link
JP (1)	JPS54130537A (fr)
AR (1)	AR241108A1 (fr)
AU (1)	AU531296B2 (fr)
BE (1)	BE874515A (fr)
BG (3)	BG48921A3 (fr)
BR (1)	BR7901221A (fr)
CA (1)	CA1237439A (fr)
CH (1)	CH638485A5 (fr)
DD (2)	DD148767A5 (fr)
DE (1)	DE2907609A1 (fr)
DK (1)	DK161830C (fr)
ES (1)	ES478426A1 (fr)
FR (1)	FR2442826A1 (fr)
GB (1)	GB2015519B (fr)
GR (1)	GR72544B (fr)
HU (1)	HU185607B (fr)
IL (1)	IL56739A0 (fr)
IN (1)	IN150228B (fr)
KE (1)	KE3293A (fr)
LU (1)	LU80981A1 (fr)
MX (1)	MX5698E (fr)
NL (1)	NL7901460A (fr)
NO (2)	NO152582C (fr)
NZ (1)	NZ189791A (fr)
PL (1)	PL135350B1 (fr)
PT (1)	PT69283A (fr)
RO (1)	RO77772A (fr)
YU (1)	YU48279A (fr)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2831193A1 (de) *	1978-07-15	1980-01-24	Bayer Ag	Fluoralkenylsubstituierte cyclopropancarbonsaeureester und ihre verwendung als insektizide
EP0010874B1 (fr) *	1978-10-27	1983-06-22	Imperial Chemical Industries Plc	Procédé de séparation des isomères optiquement actifs des acides cyclopropane carboxyliques substitués; des sels amino des acides cyclopropane carboxyliques; acide cyclopropane carboxylique substitué
DE2919820A1 (de)	1979-05-16	1980-11-20	Bayer Ag	Fluor-substituierte oxyalkenyl-cyclopropancarbonsaeureester, verfahren zu ihrer herstellung sowie ihre verwendung als insektizide und akarizide
EP0022608B1 (fr) *	1979-07-13	1983-07-06	Imperial Chemical Industries Plc	Procédé de préparation d'esters d'acides cyclopropane carboxyliques
IT1131883B (it) *	1980-07-02	1986-06-25	Montedison Spa	Processo per la sintesi stereoselettiva di ciclopropancarbossilati intermaedi per piretroidi
NZ221534A (en) *	1986-08-27	1990-10-26	Montedison Spa	Derivatives of 2,2-dimethyl-cyclopropane carboxylic acid; insecticides and acaricides
DE3900275A1 (de) *	1989-01-07	1990-07-12	Basf Ag	Substituierte cyclopropancarbonsaeurepropargylester, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung von schaedlingen
FR2687152A1 (fr) *	1992-02-07	1993-08-13	Roussel Uclaf	Nouveaux esters pyrethrinouides derives d'alcool furanique ou thiophenique, leur procede de preparation et leur application comme pesticides.
US6072074A (en) *	1998-05-08	2000-06-06	Sumitomo Chemical Company Limited	Process for producing 3-propynyl-2-2-dimethylcycloprophane-carboxylic acid and its lower akyl esters

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS515450B1 (fr)	1971-06-29	1976-02-20
DE2326077C2 (de)	1972-05-25	1985-12-12	National Research Development Corp., London	Ungesättigte Cyclopropancarbonsäuren und deren Derivate, deren Herstellung und diese enthaltende Insektizide
JPS5283720A (en) *	1976-01-01	1977-07-12	Kuraray Co Ltd	Substituted cyclopropanecarboxylic acid derivatives, and insecticides and acaricides containing a-substituted cyclopropanecarboxylic acid deri vatives
US4130655A (en) *	1976-07-12	1978-12-19	Ciba-Geigy Corporation	Pesticidal 2,2-dimethyl-3-isobutyl-cyclopropionates
DE2638356A1 (de) *	1976-08-26	1978-03-02	Bayer Ag	Verfahren zur herstellung vinylsubstituierter cyclopropancarbonsaeureester
US4183948A (en) *	1977-01-24	1980-01-15	Imperial Chemical Industries Limited	Halogenated esters
GB2008572B (en) *	1977-11-28	1982-01-27	Ici Ltd	Manufacture of esters
IN150399B (fr) *	1978-01-20	1982-09-25	Fmc Corp

1979
- 1979-02-06 BG BG044136A patent/BG48921A3/xx unknown
- 1979-02-06 BG BG044135A patent/BG48333A3/xx unknown
- 1979-02-23 NO NO790621A patent/NO152582C/no unknown
- 1979-02-23 DK DK080379A patent/DK161830C/da not_active IP Right Cessation
- 1979-02-23 BR BR7901221A patent/BR7901221A/pt unknown
- 1979-02-23 NL NL7901460A patent/NL7901460A/xx not_active Application Discontinuation
- 1979-02-26 IN IN173/CAL/79A patent/IN150228B/en unknown
- 1979-02-26 PT PT69283A patent/PT69283A/pt unknown
- 1979-02-26 GR GR58472A patent/GR72544B/el unknown
- 1979-02-26 IL IL56739A patent/IL56739A0/xx not_active IP Right Cessation
- 1979-02-26 BG BG042659A patent/BG48931A3/xx unknown
- 1979-02-27 ES ES478426A patent/ES478426A1/es not_active Expired
- 1979-02-27 GB GB7906851A patent/GB2015519B/en not_active Expired
- 1979-02-27 CA CA000322525A patent/CA1237439A/fr not_active Expired
- 1979-02-27 FR FR7904952A patent/FR2442826A1/fr active Granted
- 1979-02-27 DD DD79218658A patent/DD148767A5/de not_active IP Right Cessation
- 1979-02-27 AU AU44631/79A patent/AU531296B2/en not_active Expired
- 1979-02-27 PL PL1979213760A patent/PL135350B1/pl unknown
- 1979-02-27 YU YU00482/79A patent/YU48279A/xx unknown
- 1979-02-27 CH CH194279A patent/CH638485A5/it not_active IP Right Cessation
- 1979-02-27 DE DE19792907609 patent/DE2907609A1/de active Granted
- 1979-02-27 HU HU79MO1039A patent/HU185607B/hu unknown
- 1979-02-27 DD DD79211259A patent/DD142281A5/de not_active IP Right Cessation
- 1979-02-28 LU LU80981A patent/LU80981A1/fr unknown
- 1979-02-28 RO RO79101065A patent/RO77772A/fr unknown
- 1979-02-28 MX MX797764U patent/MX5698E/es unknown
- 1979-02-28 JP JP2204779A patent/JPS54130537A/ja active Granted
- 1979-02-28 AR AR275649A patent/AR241108A1/es active
- 1979-02-28 BE BE0/193748A patent/BE874515A/fr not_active IP Right Cessation
- 1979-02-28 NZ NZ189791A patent/NZ189791A/xx unknown
- 1979-08-21 NO NO792716A patent/NO153098C/no unknown
1983
- 1983-06-08 KE KE3293A patent/KE3293A/xx unknown

Also Published As

Publication number	Publication date
BG48921A3 (en)	1991-06-14
NZ189791A (en)	1981-03-16
PL213760A1 (pl)	1979-12-17
ES478426A1 (es)	1979-12-16
NO790621L (no)	1979-08-29
DD148767A5 (de)	1981-06-10
IN150228B (fr)	1982-08-21
MX5698E (es)	1983-12-15
KE3293A (en)	1983-07-01
AU4463179A (en)	1979-09-06
GR72544B (fr)	1983-11-17
NL7901460A (nl)	1979-08-30
BE874515A (fr)	1979-08-28
GB2015519B (en)	1982-12-15
NO153098C (no)	1986-01-15
DE2907609C2 (fr)	1991-02-14
BG48931A3 (en)	1991-06-14
YU48279A (en)	1983-04-30
NO792716L (no)	1979-08-29
DK80379A (da)	1979-09-18
JPS54130537A (en)	1979-10-09
NO153098B (no)	1985-10-07
FR2442826B1 (fr)	1984-07-06
RO77772A (fr)	1981-11-24
AR241108A1 (es)	1991-11-15
PT69283A (en)	1979-03-01
LU80981A1 (fr)	1979-06-18
GB2015519A (en)	1979-09-12
DK161830C (da)	1992-01-20
NO152582B (no)	1985-07-15
JPH0212941B2 (fr)	1990-03-30
BG48333A3 (en)	1991-01-15
NO152582C (no)	1985-10-23
AR241108A2 (es)	1991-11-15
IL56739A0 (en)	1979-05-31
HU185607B (en)	1985-03-28
CA1237439A (fr)	1988-05-31
FR2442826A1 (fr)	1980-06-27
DD142281A5 (de)	1980-06-18
AU531296B2 (en)	1983-08-18
DK161830B (da)	1991-08-19
DE2907609A1 (de)	1979-09-13
BR7901221A (pt)	1979-10-02
CH638485A5 (it)	1983-09-30

Publication	Publication Date	Title
EP0003336B1 (fr)	1984-02-22	Perhaloalcoylvinylcyclopropane carboxylates ayant une activité insecticide
US4868209A (en)	1989-09-19	Halogenated esters
US4405640A (en)	1983-09-20	Substituted fluorobenzyl cyclopropane carboxylates useful as insecticides
EP0054360B1 (fr)	1985-06-05	Esters fluorobenzyliques d'acides cyclopropanecarboxyliques, leur préparation, compositions les contenant et leur utilisation comme insecticides
US4551546A (en)	1985-11-05	Halogenated esters
US4376785A (en)	1983-03-15	Cyclopropanecarboxylates and a low fish toxic insecticide and/or acaricide containing them
PL135350B1 (pl)	1985-10-31	Method of obtaining novel pyretroides and insecticide and/or acaricide
US4341796A (en)	1982-07-27	Control of acarids with biphenylmethyl perhaloalkylvinylcyclopropanecarboxylates
US4200644A (en)	1980-04-29	Arylthiovinylcyclopropanecarboxylate insecticides
US4333950A (en)	1982-06-08	(+)-4-Substituted-2-indanol insecticidal ester derivatives
US4328237A (en)	1982-05-04	Pyrethroids
US4152455A (en)	1979-05-01	Insecticidal α-trifluoromethyl-3-phenoxybenzyl carboxylates
US4285969A (en)	1981-08-25	Pyrethroids
US4258202A (en)	1981-03-24	Cyclopropanecarboxylic acids and esters
US4335252A (en)	1982-06-15	Insecticidal pyrethroid enantiomer pair
DE3327292A1 (de)	1984-04-12	Neue verbindungen, verfahren zu ihrer herstellung und die verwendung dieser verbindungen
US4599358A (en)	1986-07-08	Pyrethroids
US4162366A (en)	1979-07-24	α-TRIFLUOROMETHYL-3-PHENOXYBENZYL ALCOHOL
US4395567A (en)	1983-07-26	1R,Cis-3-(2-halo-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylic acid derivatives
US4902697A (en)	1990-02-20	Derivatives of 2,2-dimethyl-cyclopropanecarboxylic acid
US4459308A (en)	1984-07-10	Pyrethroids
JP2823595B2 (ja)	1998-11-11	２，２―ジメチルシクロプロパンカルボン酸のエステル
US4215069A (en)	1980-07-29	Arylthiovinylcyclopropanecarboxylate intermediates
US4417078A (en)	1983-11-22	Process for producing (+)-4-substituted-2-indanols
US4423255A (en)	1983-12-27	(+)-4-Substituted-2-indanols