DD150455A6 - Verfahren zur herstellung von phenylalkansaeure-m-phenoxy-benzylestern - Google Patents

Verfahren zur herstellung von phenylalkansaeure-m-phenoxy-benzylestern Download PDF

Info

Publication number: DD150455A6
Authority: DD; German Democratic Republic
Prior art keywords: alpha; ppm; acid; preparation; main patent
Prior art date: 1978-03-20

Application number

DD79211694A

Other languages

German (de)

English (en)

Inventor

Gerald Berkelhammer

Venkataraman Kameswaran

Original Assignee

American Cyanamid Co

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.)

1978-03-20

Filing date

1979-03-20

Publication date

1981-09-02

1978-03-20 Priority claimed from US05/890,568 external-priority patent/US4199595A/en

1978-03-20 Priority claimed from US05/890,721 external-priority patent/US4178460A/en

1979-03-20 Application filed by American Cyanamid Co filed Critical American Cyanamid Co

1981-09-02 Publication of DD150455A6 publication Critical patent/DD150455A6/de

Links

238000002360 preparation method Methods 0.000 title claims abstract description 8
238000000034 method Methods 0.000 title claims description 6
-1 M-PHENOXY BENZYL ESTERS Chemical class 0.000 title abstract description 5
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 title 1
239000002253 acid Substances 0.000 claims abstract description 17
GXUQMKBQDGPMKZ-UHFFFAOYSA-N 2-hydroxy-2-(3-phenoxyphenyl)acetonitrile Chemical compound N#CC(O)C1=CC=CC(OC=2C=CC=CC=2)=C1 GXUQMKBQDGPMKZ-UHFFFAOYSA-N 0.000 claims description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 27
150000002148 esters Chemical class 0.000 abstract description 8
150000007513 acids Chemical class 0.000 abstract description 6
230000003287 optical effect Effects 0.000 abstract description 6
238000003776 cleavage reaction Methods 0.000 abstract description 4
230000007017 scission Effects 0.000 abstract description 4
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 abstract description 3
150000003839 salts Chemical class 0.000 description 6
239000000126 substance Substances 0.000 description 4
RQEUFEKYXDPUSK-ZETCQYMHSA-N (1S)-1-phenylethanamine Chemical compound C[C@H](N)C1=CC=CC=C1 RQEUFEKYXDPUSK-ZETCQYMHSA-N 0.000 description 2
241000238876 Acari Species 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
238000007792 addition Methods 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
125000004093 cyano group Chemical group *C#N 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
230000000749 insecticidal effect Effects 0.000 description 2
239000000203 mixture Substances 0.000 description 2
KGANAERDZBAECK-UHFFFAOYSA-N (3-phenoxyphenyl)methanol Chemical compound OCC1=CC=CC(OC=2C=CC=CC=2)=C1 KGANAERDZBAECK-UHFFFAOYSA-N 0.000 description 1
QPBAPUDRLFPMHV-UHFFFAOYSA-N 2-[2-benzyl-3-phenoxy-4-(trifluoromethoxy)phenyl]-2-cyano-3-methylbutanoic acid Chemical compound CC(C)C(C#N)(C1=C(C(=C(C=C1)OC(F)(F)F)OC2=CC=CC=C2)CC3=CC=CC=C3)C(=O)O QPBAPUDRLFPMHV-UHFFFAOYSA-N 0.000 description 1
QIMUYXGVXHABQI-UHFFFAOYSA-N 3-methyl-2-[4-(trifluoromethoxy)phenyl]butanoic acid Chemical compound CC(C)C(C(O)=O)C1=CC=C(OC(F)(F)F)C=C1 QIMUYXGVXHABQI-UHFFFAOYSA-N 0.000 description 1
241001124076 Aphididae Species 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
241001414720 Cicadellidae Species 0.000 description 1
241000256113 Culicidae Species 0.000 description 1
241000238631 Hexapoda Species 0.000 description 1
241000208125 Nicotiana Species 0.000 description 1
235000002637 Nicotiana tabacum Nutrition 0.000 description 1
241000985245 Spodoptera litura Species 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000011324 bead Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
230000000694 effects Effects 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
229960003424 phenylacetic acid Drugs 0.000 description 1
239000003279 phenylacetic acid Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
WVVDSMCPJKZVJJ-UHFFFAOYSA-N propan-2-yl 2-[4-(difluoromethoxy)phenyl]acetate Chemical compound C(C)(C)OC(CC1=CC=C(C=C1)OC(F)F)=O WVVDSMCPJKZVJJ-UHFFFAOYSA-N 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010583 slow cooling Methods 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/10—Aromatic or araliphatic carboxylic acids, or thio analogues thereof; Derivatives thereof
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/34—Nitriles
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
- A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
- 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
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/10—Sulfones; Sulfoxides
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/38—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by esterified hydroxy groups
- 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
- C07C45/70—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 reaction with functional groups containing oxygen only in singly bound form
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C07C47/575—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing ether groups, groups, groups, or groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/08—Preparation of carboxylic acids or their salts, halides or anhydrides from nitriles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/363—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/612—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/612—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety
- C07C69/614—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety of phenylacetic acid

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Dentistry (AREA)
Plant Pathology (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Pest Control & Pesticides (AREA)
Agronomy & Crop Science (AREA)
Chemical Kinetics & Catalysis (AREA)
Oil, Petroleum & Natural Gas (AREA)
Veterinary Medicine (AREA)
Tropical Medicine & Parasitology (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

DD79211694A 1978-03-20 1979-03-20 Verfahren zur herstellung von phenylalkansaeure-m-phenoxy-benzylestern DD150455A6 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US05/890,568 US4199595A (en)	1976-10-01	1978-03-20	M-phenoxybenzyl and α-cyano-M-phenoxybenzyl esters of 2-haloalkyl (oxy-, thio-, sulfinyl-, or sulfonyl)phenylalkanoic acids
US05/890,721 US4178460A (en)	1976-10-01	1978-03-20	2-Haloalkyl(oxy-, thio-, sulfinyl-, or sulfonyl)-phenylalkanoic acids

Publications (1)

Publication Number	Publication Date
DD150455A6 true DD150455A6 (de)	1981-09-02

Family

ID=27128953

Family Applications (5)

Application Number	Title	Priority Date	Filing Date
DD79211693A DD143601A5 (de)	1978-03-20	1979-03-20	Verfahren zur herstellung von phenylalkansaeure-m-phenoxybenzylestern
DD79220465A DD154535A5 (de)	1978-03-20	1979-03-20	Verfahren zur herstellung von (+)-alpha-isopropyl-4-di-oder-trifluormethoxyphenylessigsaeure
DD79211694A DD150455A6 (de)	1978-03-20	1979-03-20	Verfahren zur herstellung von phenylalkansaeure-m-phenoxy-benzylestern
DD79219673A DD149601A6 (de)	1978-03-20	1979-03-20	Verfahren zur bekaempfung von insekten und milben
DD79220007A DD152539A5 (de)	1978-03-20	1979-03-20	Verfahren zur herstellung von phenylalkansaeuren

Family Applications Before (2)

Application Number	Title	Priority Date	Filing Date
DD79211693A DD143601A5 (de)	1978-03-20	1979-03-20	Verfahren zur herstellung von phenylalkansaeure-m-phenoxybenzylestern
DD79220465A DD154535A5 (de)	1978-03-20	1979-03-20	Verfahren zur herstellung von (+)-alpha-isopropyl-4-di-oder-trifluormethoxyphenylessigsaeure

Family Applications After (2)

Application Number	Title	Priority Date	Filing Date
DD79219673A DD149601A6 (de)	1978-03-20	1979-03-20	Verfahren zur bekaempfung von insekten und milben
DD79220007A DD152539A5 (de)	1978-03-20	1979-03-20	Verfahren zur herstellung von phenylalkansaeuren

Country Status (17)

Country	Link
JP (1)	JPS54135742A (el)
AR (1)	AR228014A1 (el)
AT (1)	AT367965B (el)
AU (2)	AU525146B2 (el)
BR (1)	BR7901697A (el)
CH (2)	CH640513A5 (el)
DD (5)	DD143601A5 (el)
DK (1)	DK112679A (el)
ES (2)	ES478785A0 (el)
GB (1)	GB2017688B (el)
GR (1)	GR74446B (el)
HU (1)	HU182016B (el)
NL (1)	NL7902153A (el)
NZ (1)	NZ189915A (el)
PL (1)	PL123011B1 (el)
RO (1)	RO79551A (el)
SE (1)	SE444313B (el)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2837524A1 (de) *	1978-08-28	1980-03-20	Bayer Ag	Substituierte alpha-phenyl-carbonsaeure- (4-fluoro-3-phenoxy-benzyl)-ester, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide
IL61348A (en) *	1979-11-28	1984-05-31	American Cyanamid Co	(-)-alpha-cyano-m-phenoxybenzyl(+)alpha-isopropyl-4-difluoromethoxy-phenylacetate,its preparation and its use as an insecticide
JPS56133253A (en) *	1980-03-24	1981-10-19	Sumitomo Chem Co Ltd	Optical isomer of cyanohydrin ester, its production and insecticide and acaricide containing the same as effective ingredient
JPS56139445A (en) *	1980-04-02	1981-10-30	Sumitomo Chem Co Ltd	Stereoisomer of cyanohydrin ester, its production and insecticide, acaricide containing the same as active principle
JPS5793948A (en) *	1980-12-02	1982-06-11	Sumitomo Chem Co Ltd	Preparation of stereoisomer mixture of higher active phenylacetic ester derivative
DE3103325A1 (de) *	1981-01-31	1982-08-26	Bayer Ag, 5090 Leverkusen	4-fluor-3-halophenoxy-benzylester, verfahren zu deren herstellung und deren verwendung in schaedlingsbekaempfungsmitteln sowie neue zwischenprodukte und verfahren zu deren herstellung
FR2512815B1 (fr) *	1981-04-16	1989-04-14	Roussel Uclaf	Nouveaux derives de l'acide cyclopropane carboxylique, leur procede de preparation, leur application a la lutte contre les parasites
IL69304A0 (en) *	1982-08-23	1983-11-30	American Cyanamid Co	Method for the preparation of difluoromethoxyaromatic compounds

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5133612B2 (el) *	1973-04-19	1976-09-21	Sumitomo Chemical Co
IL52973A (en) *	1976-10-01	1983-10-31	American Cyanamid Co	Alpha-(haloalkoxy and haloalkyl-thiophenyl)alkanoic acid ester derivatives,their preparation and insecticidal and acaricidal compositions containing them

1979
- 1979-02-16 GR GR58388A patent/GR74446B/el unknown
- 1979-03-15 NZ NZ189915A patent/NZ189915A/xx unknown
- 1979-03-17 RO RO7996953A patent/RO79551A/ro unknown
- 1979-03-19 CH CH257479A patent/CH640513A5/de not_active IP Right Cessation
- 1979-03-19 NL NL7902153A patent/NL7902153A/xx not_active Application Discontinuation
- 1979-03-19 AU AU45242/79A patent/AU525146B2/en not_active Ceased
- 1979-03-19 AT AT0204979A patent/AT367965B/de not_active IP Right Cessation
- 1979-03-19 PL PL1979214234A patent/PL123011B1/pl unknown
- 1979-03-19 SE SE7902467A patent/SE444313B/sv not_active IP Right Cessation
- 1979-03-19 CH CH257379A patent/CH641638A5/de not_active IP Right Cessation
- 1979-03-19 GB GB7909542A patent/GB2017688B/en not_active Expired
- 1979-03-19 AU AU45251/79A patent/AU528525B2/en not_active Expired
- 1979-03-19 BR BR7901697A patent/BR7901697A/pt unknown
- 1979-03-19 DK DK112679A patent/DK112679A/da not_active Application Discontinuation
- 1979-03-20 ES ES1979478785A patent/ES478785A0/es active Granted
- 1979-03-20 AR AR275883A patent/AR228014A1/es active
- 1979-03-20 HU HU79AE565A patent/HU182016B/hu unknown
- 1979-03-20 DD DD79211693A patent/DD143601A5/de unknown
- 1979-03-20 DD DD79220465A patent/DD154535A5/de unknown
- 1979-03-20 ES ES478787A patent/ES8105253A1/es not_active Expired
- 1979-03-20 DD DD79211694A patent/DD150455A6/de not_active IP Right Cessation
- 1979-03-20 DD DD79219673A patent/DD149601A6/de unknown
- 1979-03-20 JP JP3318979A patent/JPS54135742A/ja active Granted
- 1979-03-20 DD DD79220007A patent/DD152539A5/de unknown

Also Published As

Publication number	Publication date
SE7902467L (el)	1979-11-19
AU4525179A (en)	1979-09-27
JPS54135742A (en)	1979-10-22
PL214234A3 (el)	1980-08-25
AU528525B2 (en)	1983-05-05
DK112679A (da)	1979-09-21
ATA204979A (de)	1982-01-15
AR228014A1 (es)	1983-01-14
BR7901697A (pt)	1979-10-16
ES8303283A2 (es)	1983-02-01
HU182016B (en)	1983-12-28
GB2017688A (en)	1979-10-10
ES478785A0 (es)	1983-02-01
RO79551A (ro)	1982-08-17
DD143601A5 (de)	1980-09-03
DD154535A5 (de)	1982-03-31
NZ189915A (en)	1981-04-24
PL123011B1 (en)	1982-09-30
DD152539A5 (de)	1981-12-02
AU525146B2 (en)	1982-10-21
GR74446B (el)	1984-06-28
AT367965B (de)	1982-08-25
AU4524279A (en)	1979-09-27
CH641638A5 (de)	1984-03-15
ES478787A0 (es)	1981-05-16
CH640513A5 (de)	1984-01-13
GB2017688B (en)	1982-08-18
DD149601A6 (de)	1981-07-22
JPS6362507B2 (el)	1988-12-02
SE444313B (sv)	1986-04-07
NL7902153A (nl)	1979-09-24
ES8105253A1 (es)	1981-05-16

Legal Events

Date	Code	Title	Description
1995-05-24	PV	Patent disclaimer (addendum to changes before extension act)

Publication	Publication Date	Title
DE2653189C2 (de)	1985-02-14	Cyclopropanverbindungen, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Insektizide
DE2439177C2 (de)	1984-02-02	(±)-&alpha;-Cyan-3-phenoxybenzyl-(1R,trans)- und (1R,cis)-2,2-dimethyl-3-(2,2-dibromvinyl)-cyclopropancarboxylat und (S)-&alpha;-Cyan-3-phenoxybenzyl-(1R,cis)-2,2-dimethyl-3-(2,2-dibromvinyl)-cyclopropancarboxylat, Verfahren zur Herstellung des (S)-Isomeren und diese Verbindungen enthaltende Insektizide
EP0011695A1 (de)	1980-06-11	Substituierte Cyclopropancarbonsäuren und deren Derivate; Verfahren zu deren Herstellung und ihre Verwendung zur Herstellung von Insektiziden und Akariziden
CH638171A5 (de)	1983-09-15	Substituierte cyclopropancarbonsaeureester.
DE1140580B (de)	1962-12-06	Verfahren zur Herstellung von Thionophosphonsaeureestern
DE1668603C3 (el)	1974-08-22
DE3941966A1 (de)	1991-06-20	Halogenierte olefine, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel
DD150455A6 (de)	1981-09-02	Verfahren zur herstellung von phenylalkansaeure-m-phenoxy-benzylestern
EP0012722B1 (de)	1981-12-09	Verfahren zur Herstellung von optisch aktiven, in 3-Stellung substituierten 2-(2',2'-Dihalogenvinyl)-cyclopropan-1-carbonsäuren und deren Derivaten; 4-(2',2',2'-Trihalogenäthyl)-cyclobutan-1-sulfonsäuresalze und deren Herstellung
DE2734667A1 (de)	1978-02-09	Derivate von phenoxyalkansaeuren, verfahren zu ihrer herstellung und ihre verwendung als herbicide
US3054719A (en)	1962-09-18	Acaricidal poly-halo diphenylsulfide
EP0161543B1 (de)	1988-03-02	Neue Halogenvinylbenzylester, deren Herstellung und Verwendung zur Schädlingsbekämpfung
DE1138048B (de)	1962-10-18	Verfahren zur Herstellung von (Thiono)Phosphon- bzw. (Thiono)Phosphinsaeureestern der ª- und ª-Naphthole
EP0046950B1 (de)	1984-04-11	Optisch aktive Isomere von trans-3-(2-Chlor-2-(4-chlor-phenyl)-vinyl)-2,2-dimethyl-cyclopropan-1-carbonsäure-(alpha-cyano-4-fluor-3-phenoxy-benzyl)-ester, Verfahren zu deren Herstellung und deren Verwendung als Ektoparasitizide
DE2608506C2 (de)	1983-12-15	Neue 0,0-Dialkyl-(di)thiophosphorsäureester, ihre Herstellung sowie ihre Verwendung in insektiziden und akariziden Zusammensetzungen
DE2909827A1 (de)	1979-10-04	Phenylalkansaeure-m-phenoxybenzylester, verfahren zu ihrer herstellung und deren verwendung
DE1959401B2 (de)	1980-03-27	Verfahren zur Herstellung von in 2-SteIlung substituierten trans-33-Dimethyl-cyclopropan-1 -carbonsäuren
DE1027208B (de)	1958-04-03	Verfahren zur Herstellung von insekticid wirksamen basischen Phosphorsaeureestern
DE2554883A1 (de)	1976-06-16	Insektizide ester
AT228804B (de)	1963-08-12	Verfahren zur Herstellung von Thionothiolphosphorsäureestern
DE1036846B (de)	1958-08-21	Verfahren zur Herstellung von Thiophosphorsaeureestern
DE1204667C2 (de)	1973-01-25	Verfahren zur Herstellung von unsymmetrischen Thionothiolphorsphorsaeureestern
AT226251B (de)	1963-03-11	Verfahren zur Herstellung von neuen Thiophosphorsäureestern
DE1117110B (de)	1961-11-16	Verfahren zur Herstellung von Thionophosphorsaeureestern
AT214454B (de)	1961-04-10	Verfahren zur Herstellung neuer Phosphinsäurederivate