PL129811B1 - Method of manufacture of derivatives of ester of cyclopropanecarboxylic acid and pesticide - Google Patents

Method of manufacture of derivatives of ester of cyclopropanecarboxylic acid and pesticide

Info

Publication number: PL129811B1
Authority: PL; Poland
Prior art keywords: isomers; irciss; mixture; iscisr; ircisr
Prior art date: 1979-11-27

Application number

PL1980228060A

Other languages

English (en)

Polish (pl)

Other versions

PL228060A1 (es

Original Assignee

Shell Internationale Research Maatschappij Bv

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.)

1979-11-27

Filing date

1980-11-25

Publication date

1984-06-30

1980-11-25 Application filed by Shell Internationale Research Maatschappij Bv filed Critical Shell Internationale Research Maatschappij Bv

1981-07-24 Publication of PL228060A1 publication Critical patent/PL228060A1/xx

1984-06-30 Publication of PL129811B1 publication Critical patent/PL129811B1/pl

Links

238000000034 method Methods 0.000 title claims description 22
239000000575 pesticide Substances 0.000 title claims description 7
150000002148 esters Chemical class 0.000 title description 12
YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 title description 5
238000004519 manufacturing process Methods 0.000 title description 2
239000000203 mixture Substances 0.000 claims description 50
150000001875 compounds Chemical class 0.000 claims description 36
125000004432 carbon atom Chemical group C* 0.000 claims description 13
239000007787 solid Substances 0.000 claims description 12
239000007788 liquid Substances 0.000 claims description 10
239000002904 solvent Substances 0.000 claims description 9
-1 cyclopropanecarboxylic acid ester Chemical class 0.000 claims description 8
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 claims description 7
229910052801 chlorine Inorganic materials 0.000 claims description 6
125000001309 chloro group Chemical group Cl* 0.000 claims description 5
239000013543 active substance Substances 0.000 claims description 4
150000001335 aliphatic alkanes Chemical class 0.000 claims description 3
239000000243 solution Substances 0.000 description 25
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
239000002585 base Substances 0.000 description 16
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
238000002844 melting Methods 0.000 description 13
230000008018 melting Effects 0.000 description 13
239000004480 active ingredient Substances 0.000 description 11
238000002425 crystallisation Methods 0.000 description 11
230000008025 crystallization Effects 0.000 description 11
239000003795 chemical substances by application Substances 0.000 description 10
239000003208 petroleum Substances 0.000 description 10
239000000047 product Substances 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
238000004811 liquid chromatography Methods 0.000 description 8
239000007858 starting material Substances 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 7
230000000361 pesticidal effect Effects 0.000 description 7
LLMLSUSAKZVFOA-UHFFFAOYSA-N 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(O)=O LLMLSUSAKZVFOA-UHFFFAOYSA-N 0.000 description 6
239000002270 dispersing agent Substances 0.000 description 6
239000000839 emulsion Substances 0.000 description 6
238000002360 preparation method Methods 0.000 description 6
239000002253 acid Substances 0.000 description 5
239000012141 concentrate Substances 0.000 description 5
239000013078 crystal Substances 0.000 description 5
239000000843 powder Substances 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
238000001914 filtration Methods 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
230000006340 racemization Effects 0.000 description 4
239000003381 stabilizer Substances 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
239000000654 additive Substances 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
239000000969 carrier Substances 0.000 description 3
229920001429 chelating resin Polymers 0.000 description 3
238000010410 dusting Methods 0.000 description 3
239000008187 granular material Substances 0.000 description 3
230000000149 penetrating effect Effects 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
239000012265 solid product Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000000126 substance Substances 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
239000004094 surface-active agent Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
150000008041 alkali metal carbonates Chemical class 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
235000011114 ammonium hydroxide Nutrition 0.000 description 2
239000002518 antifoaming agent Substances 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
238000005260 corrosion Methods 0.000 description 2
230000007797 corrosion Effects 0.000 description 2
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
239000003995 emulsifying agent Substances 0.000 description 2
239000003623 enhancer Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000003444 phase transfer catalyst Substances 0.000 description 2
239000002574 poison Substances 0.000 description 2
231100000614 poison Toxicity 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
230000001681 protective effect Effects 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000000926 separation method Methods 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
239000004546 suspension concentrate Substances 0.000 description 2
239000004563 wettable powder Substances 0.000 description 2
BFNMOMYTTGHNGJ-UHFFFAOYSA-N 2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)CC1C(O)=O BFNMOMYTTGHNGJ-UHFFFAOYSA-N 0.000 description 1
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 1
241000238876 Acari Species 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
239000005946 Cypermethrin Substances 0.000 description 1
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
241000238631 Hexapoda Species 0.000 description 1
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 1
241000899717 Itaya Species 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
241000256250 Spodoptera littoralis Species 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
241000607479 Yersinia pestis Species 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
238000005054 agglomeration Methods 0.000 description 1
230000002776 aggregation Effects 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
125000005263 alkylenediamine group Chemical group 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
239000005667 attractant Substances 0.000 description 1
HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical class [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
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 description 1
150000003842 bromide salts Chemical class 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
239000004927 clay Substances 0.000 description 1
239000008119 colloidal silica Substances 0.000 description 1
239000000084 colloidal system Substances 0.000 description 1
238000013270 controlled release Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000006184 cosolvent Substances 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
229960005424 cypermethrin Drugs 0.000 description 1
238000010908 decantation Methods 0.000 description 1
238000007865 diluting Methods 0.000 description 1
238000003113 dilution method Methods 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
230000009969 flowable effect Effects 0.000 description 1
235000012041 food component Nutrition 0.000 description 1
239000005417 food ingredient Substances 0.000 description 1
230000008014 freezing Effects 0.000 description 1
238000007710 freezing Methods 0.000 description 1
230000000855 fungicidal effect Effects 0.000 description 1
229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
150000004676 glycans Chemical class 0.000 description 1
230000002363 herbicidal effect Effects 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
238000005470 impregnation Methods 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
239000008268 mayonnaise Substances 0.000 description 1
235000010746 mayonnaise Nutrition 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000003094 microcapsule Substances 0.000 description 1
239000003607 modifier Substances 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000006259 organic additive Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
239000003016 pheromone Substances 0.000 description 1
238000000053 physical method Methods 0.000 description 1
229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
229920001282 polysaccharide Polymers 0.000 description 1
239000005017 polysaccharide Substances 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
239000002728 pyrethroid Substances 0.000 description 1
239000002994 raw material Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
238000004062 sedimentation Methods 0.000 description 1
239000002689 soil Substances 0.000 description 1
239000007790 solid phase Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
239000012085 test solution Substances 0.000 description 1
DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
239000013008 thixotropic agent Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- 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

Landscapes

Life Sciences & Earth Sciences (AREA)
Agronomy & Crop Science (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

PL1980228060A 1979-11-27 1980-11-25 Method of manufacture of derivatives of ester of cyclopropanecarboxylic acid and pesticide PL129811B1 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB7940856		1979-11-27
GB7940857		1979-11-27

Publications (2)

Publication Number	Publication Date
PL228060A1 PL228060A1 (es)	1981-07-24
PL129811B1 true PL129811B1 (en)	1984-06-30

Family

ID=26273687

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
PL1980228060A PL129811B1 (en)	1979-11-27	1980-11-25	Method of manufacture of derivatives of ester of cyclopropanecarboxylic acid and pesticide

Country Status (25)

Country	Link
AU (1)	AU6467780A (es)
BG (1)	BG42352A3 (es)
BR (1)	BR8007688A (es)
CA (1)	CA1150301A (es)
CH (1)	CH646837A5 (es)
CS (1)	CS219296B2 (es)
DD (1)	DD154973A5 (es)
DE (1)	DE3044391A1 (es)
DK (1)	DK501880A (es)
ES (1)	ES8201940A1 (es)
FR (1)	FR2470117A1 (es)
GB (1)	GB2064528B (es)
IE (1)	IE50479B1 (es)
IL (1)	IL61557A0 (es)
IN (1)	IN155143B (es)
IT (1)	IT1134448B (es)
MX (1)	MX6132E (es)
NL (1)	NL8006398A (es)
NZ (1)	NZ195637A (es)
OA (1)	OA06708A (es)
PL (1)	PL129811B1 (es)
RO (1)	RO80004A (es)
SE (1)	SE453079B (es)
SU (1)	SU1068036A3 (es)
YU (1)	YU41954B (es)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA1162560A (en) *	1980-04-23	1984-02-21	Ronald F. Mason	Process for preparing cyclopropane carboxylic acid ester derivatives
EP0106469B1 (en) *	1982-10-11	1987-01-14	Imperial Chemical Industries Plc	Insecticidal product and preparation thereof
DE3372480D1 (en) *	1982-10-18	1987-08-20	Ici Plc	Insecticidal product and preparation thereof
GB8418331D0 (en) *	1984-07-18	1984-08-22	Ici Plc	Insecticidal ester
CA1275108A (en) *	1985-01-16	1990-10-09	Laszlo Pap	Insecticidal composition comprising more than one active ingredients
DE3522629A1 (de) *	1985-06-25	1987-01-08	Bayer Ag	Verfahren zur herstellung bestimmter enantiomerenpaare von permethrinsaeure-(alpha)-cyano-3-phenoxy-4-fluor-benzyl -ester
US4997970A (en) *	1987-06-15	1991-03-05	Fmc Corporation	Conversion of pyrethroid isomers to move active species
CA1314559C (en) *	1987-06-15	1993-03-16	John Winfrid Ager	Conversion of pyrethroid isomers to more active species
DE69001866T2 (de) *	1989-01-17	1993-09-23	Chinoin Gyogyszer Es Vegyeszet	Verfahren zur herstellung von cypermethrin-isomeren.
US5128497A (en) *	1990-01-03	1992-07-07	Fmc Corporation	Conversion of pyrethroid isomers to more active species

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4152410A (en) *	1975-09-03	1979-05-01	Eisai Co., Ltd.	Diagnosis reagent for neoplasm and method for diagnosis of neoplasm
FR2375161A1 (fr) *	1976-04-23	1978-07-21	Roussel Uclaf	Procede de transformation d'un ester d'acide chiral d'alcool secondaire a-cyane optiquement actif de structure (r) en ester d'acide chiral d'alcool secondaire a-cyane de structure (s)
FR2348901A1 (fr) *	1976-04-23	1977-11-18	Roussel Uclaf	Procede de transformation d'un ester d'acide chiral d'alcool secondaire alpha-cyane optiquement actif en ester d'acide chiral d'alcool secondaire alpha-cyane racemique
US4261921A (en) *	1979-06-06	1981-04-14	Fmc Corporation	Process for preparation of a crystalline insecticidal pyrethroid enantiomer pair

1980
- 1980-10-10 CA CA000362132A patent/CA1150301A/en not_active Expired
- 1980-11-21 OA OA57259A patent/OA06708A/xx unknown
- 1980-11-23 SU SU803007801A patent/SU1068036A3/ru active
- 1980-11-24 NL NL8006398A patent/NL8006398A/nl not_active Application Discontinuation
- 1980-11-25 FR FR8024980A patent/FR2470117A1/fr active Pending
- 1980-11-25 YU YU2988/80A patent/YU41954B/xx unknown
- 1980-11-25 MX MX809176U patent/MX6132E/es unknown
- 1980-11-25 AU AU64677/80A patent/AU6467780A/en not_active Abandoned
- 1980-11-25 PL PL1980228060A patent/PL129811B1/pl unknown
- 1980-11-25 DK DK501880A patent/DK501880A/da not_active Application Discontinuation
- 1980-11-25 DD DD80225458A patent/DD154973A5/de unknown
- 1980-11-25 IT IT26215/80A patent/IT1134448B/it active
- 1980-11-25 GB GB8037693A patent/GB2064528B/en not_active Expired
- 1980-11-25 BR BR8007688A patent/BR8007688A/pt not_active IP Right Cessation
- 1980-11-25 CS CS808146A patent/CS219296B2/cs unknown
- 1980-11-25 BG BG8049773A patent/BG42352A3/xx unknown
- 1980-11-25 DE DE19803044391 patent/DE3044391A1/de not_active Withdrawn
- 1980-11-25 IN IN836/DEL/80A patent/IN155143B/en unknown
- 1980-11-25 IE IE2442/80A patent/IE50479B1/en not_active IP Right Cessation
- 1980-11-25 IL IL61557A patent/IL61557A0/xx unknown
- 1980-11-25 CH CH871980A patent/CH646837A5/de not_active IP Right Cessation
- 1980-11-25 ES ES497098A patent/ES8201940A1/es not_active Expired
- 1980-11-25 NZ NZ195637A patent/NZ195637A/xx unknown
- 1980-11-25 RO RO80102679A patent/RO80004A/ro unknown
- 1980-11-25 SE SE8008254A patent/SE453079B/sv not_active IP Right Cessation

Also Published As

Publication number	Publication date
IT1134448B (it)	1986-08-13
IE802442L (en)	1981-05-27
NZ195637A (en)	1983-09-30
OA06708A (fr)	1982-05-30
RO80004A (ro)	1982-10-11
DE3044391A1 (de)	1981-08-27
DD154973A5 (de)	1982-05-05
GB2064528B (en)	1983-10-19
SE453079B (sv)	1988-01-11
BG42352A3 (en)	1987-11-14
SE8008254L (sv)	1981-05-28
IN155143B (es)	1985-01-05
AU6467780A (en)	1981-06-04
ES497098A0 (es)	1982-01-01
DK501880A (da)	1981-05-28
YU41954B (en)	1988-02-29
BR8007688A (pt)	1981-06-09
FR2470117A1 (fr)	1981-05-29
CS219296B2 (en)	1983-03-25
ES8201940A1 (es)	1982-01-01
SU1068036A3 (ru)	1984-01-15
IT8026215A0 (it)	1980-11-25
IL61557A0 (en)	1980-12-31
NL8006398A (nl)	1981-07-01
CH646837A5 (de)	1984-12-28
GB2064528A (en)	1981-06-17
IE50479B1 (en)	1986-04-30
MX6132E (es)	1984-11-22
CA1150301A (en)	1983-07-19
YU298880A (en)	1984-02-29
PL228060A1 (es)	1981-07-24

Publication	Publication Date	Title
US3979424A (en)	1976-09-07	Pesticidal cyclopropane derivatives
US5013754A (en)	1991-05-07	Insecticidal composition comprising more than one active ingredient
PL129811B1 (en)	1984-06-30	Method of manufacture of derivatives of ester of cyclopropanecarboxylic acid and pesticide
US5064859A (en)	1991-11-12	Licidal compositions containing carboxylic acids
NO124640B (es)	1972-05-15
CA1140556A (en)	1983-02-01	Pyrazole derivatives and their use as pesticides
US4297496A (en)	1981-10-27	Nitrimine derivatives
CA1123452A (en)	1982-05-11	Cyclopropyl carboxylate compounds a process for their manufacture and their use as pesticides
NO169117B (no)	1992-02-03	Fremgangsmaate for fremstilling av en hydrocarbonblanding hvis c5+-fraksjon har et hoeyt innhold av forgrenede c5- og c6-parafiner, fra en blanding carbonmonoxyd og hydrogen
JPS6360737B2 (es)	1988-11-25
US4045575A (en)	1977-08-30	Thioamide pesticides
US4431442A (en)	1984-02-14	2-Methylenesuccinamic acid compounds as plant growth regulants
US4305934A (en)	1981-12-15	Pyrethroid pesticidal compositions
US4012522A (en)	1977-03-15	Pesticidal cyclopropane derivatives
US4308262A (en)	1981-12-29	Pyrethroid pesticidal compositions
GB1594261A (en)	1981-07-30	Benzyloxime ethers
HU184176B (en)	1984-07-30	Anchoring device for floating machines particularly floating dredgers
US4346092A (en)	1982-08-24	Insecticidal combinations
US4175134A (en)	1979-11-20	Phenoxybenzyl ester pesticides
EP0002091B1 (en)	1981-06-10	Method of controlling acarid pests by means of cyclopropane carboxylate esters, the use of such esters as an acaricide, and one of said esters as a novel compound
US4025632A (en)	1977-05-24	Acaricidal pyridinium salts
BG98874A (bg)	1995-03-31	Метод за изомеризиране
US4096275A (en)	1978-06-20	Thioamide pesticides
EP0114705B1 (en)	1987-12-09	Pesticidal nitromethane derivatives
KR800000790B1 (ko)	1980-08-11	사이클로프로판 유도체의 제조방법