DD280097A5 - Verfahren zur herstellung neuer cyclopropancarbonsaeureester - Google Patents

Verfahren zur herstellung neuer cyclopropancarbonsaeureester Download PDF

Info

Publication number: DD280097A5
Authority: DD; German Democratic Republic
Prior art keywords: alpha; dimethyl; radical; formula; propenyl
Prior art date: 1987-02-06

Application number

DD88312674A

Other languages

German (de)

English (en)

Inventor

Joseph Cadiergue

Jacques Demassey

Jean-Pierre Demoute

Jean Tessier

Original Assignee

��`��k��

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.)

1987-02-06

Filing date

1988-02-04

Publication date

1990-06-27

1988-02-04 Application filed by ��`��k�� filed Critical ��`��k��

1990-06-27 Publication of DD280097A5 publication Critical patent/DD280097A5/de

Links

239000002253 acid Substances 0.000 title claims description 35
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238000004519 manufacturing process Methods 0.000 title description 4
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150000001875 compounds Chemical class 0.000 claims abstract description 49
125000003118 aryl group Chemical group 0.000 claims abstract description 21
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 20
239000000460 chlorine Substances 0.000 claims abstract description 10
229910052731 fluorine Inorganic materials 0.000 claims abstract description 9
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 7
229910052801 chlorine Inorganic materials 0.000 claims abstract description 6
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 4
239000011737 fluorine Substances 0.000 claims abstract description 4
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims abstract 2
-1 substituted alkyl radical Chemical class 0.000 claims description 144
238000000034 method Methods 0.000 claims description 57
239000000203 mixture Substances 0.000 claims description 57
150000003254 radicals Chemical class 0.000 claims description 47
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 39
150000004702 methyl esters Chemical class 0.000 claims description 38
230000008569 process Effects 0.000 claims description 32
125000004432 carbon atom Chemical group C* 0.000 claims description 31
238000002360 preparation method Methods 0.000 claims description 27
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 claims description 20
244000045947 parasite Species 0.000 claims description 18
150000007513 acids Chemical class 0.000 claims description 17
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239000004480 active ingredient Substances 0.000 claims description 16
239000007858 starting material Substances 0.000 claims description 15
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125000005843 halogen group Chemical group 0.000 claims description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
241000196324 Embryophyta Species 0.000 claims description 9
150000005840 aryl radicals Chemical class 0.000 claims description 8
KGANAERDZBAECK-UHFFFAOYSA-N (3-phenoxyphenyl)methanol Chemical compound OCC1=CC=CC(OC=2C=CC=CC=2)=C1 KGANAERDZBAECK-UHFFFAOYSA-N 0.000 claims description 7
230000000895 acaricidal effect Effects 0.000 claims description 7
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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 6
125000001153 fluoro group Chemical group F* 0.000 claims description 6
230000001069 nematicidal effect Effects 0.000 claims description 5
239000000546 pharmaceutical excipient Substances 0.000 claims description 5
AFEOKIGLYCQHAZ-UHFFFAOYSA-N (5-benzylfuran-3-yl)methanol Chemical compound OCC1=COC(CC=2C=CC=CC=2)=C1 AFEOKIGLYCQHAZ-UHFFFAOYSA-N 0.000 claims description 4
QQHOVRKETYPQHY-UHFFFAOYSA-N 2-(hydroxymethyl)-4,5,6,7-tetrahydroisoindole-1,3-dione Chemical compound O=C1N(CO)C(=O)C2=C1CCCC2 QQHOVRKETYPQHY-UHFFFAOYSA-N 0.000 claims description 4
KZYVOZABVXLALY-UHFFFAOYSA-N 4-hydroxy-3-methyl-2-prop-2-enylcyclopent-2-en-1-one Chemical compound CC1=C(CC=C)C(=O)CC1O KZYVOZABVXLALY-UHFFFAOYSA-N 0.000 claims description 4
230000009471 action Effects 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
VJFUPGQZSXIULQ-XIGJTORUSA-N pyrethrin II Chemical class CC1(C)[C@H](/C=C(\C)C(=O)OC)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 VJFUPGQZSXIULQ-XIGJTORUSA-N 0.000 claims description 4
125000004122 cyclic group Chemical group 0.000 claims description 3
125000003107 substituted aryl group Chemical group 0.000 claims description 3
VTJMSIIXXKNIDJ-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-methylbutyric acid Chemical class CC(C)C(C(O)=O)C1=CC=C(Cl)C=C1 VTJMSIIXXKNIDJ-UHFFFAOYSA-N 0.000 claims description 2
MDIQXIJPQWLFSD-UHFFFAOYSA-N 3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane-1-carboxylic acid Chemical class CC1(C)C(C=C(Br)Br)C1C(O)=O MDIQXIJPQWLFSD-UHFFFAOYSA-N 0.000 claims description 2
LLMLSUSAKZVFOA-UHFFFAOYSA-N 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid Chemical class CC1(C)C(C=C(Cl)Cl)C1C(O)=O LLMLSUSAKZVFOA-UHFFFAOYSA-N 0.000 claims description 2
GJRLRWILVCEVKI-UHFFFAOYSA-N 3-[2-fluoro-3-[(2-methylpropan-2-yl)oxy]-3-oxoprop-1-enyl]-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC(C)(C)OC(=O)C(F)=CC1C(C(O)=O)C1(C)C GJRLRWILVCEVKI-UHFFFAOYSA-N 0.000 claims description 2
235000007516 Chrysanthemum Nutrition 0.000 claims description 2
239000000969 carrier Substances 0.000 claims description 2
UIWNHGWOYRFCSF-KTERXBQFSA-N (1r,3r)-3-[(e)-3-methoxy-2-methyl-3-oxoprop-1-enyl]-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound COC(=O)C(\C)=C\[C@@H]1[C@@H](C(O)=O)C1(C)C UIWNHGWOYRFCSF-KTERXBQFSA-N 0.000 claims 1
244000189548 Chrysanthemum x morifolium Species 0.000 claims 1
UIWNHGWOYRFCSF-UHFFFAOYSA-N Pyrethric acid Natural products COC(=O)C(C)=CC1C(C(O)=O)C1(C)C UIWNHGWOYRFCSF-UHFFFAOYSA-N 0.000 claims 1
241000607479 Yersinia pestis Species 0.000 claims 1
229910052739 hydrogen Inorganic materials 0.000 abstract description 29
239000001257 hydrogen Substances 0.000 abstract description 29
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 14
229910052757 nitrogen Inorganic materials 0.000 abstract description 3
230000000361 pesticidal effect Effects 0.000 abstract description 3
238000006243 chemical reaction Methods 0.000 description 70
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 65
KXGVEGMKQFWNSR-LLQZFEROSA-N deoxycholic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 KXGVEGMKQFWNSR-LLQZFEROSA-N 0.000 description 58
239000000047 product Substances 0.000 description 58
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
OKKJLVBELUTLKV-UHFFFAOYSA-N methyl alcohol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 49
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 48
239000002904 solvent Substances 0.000 description 38
235000019441 ethanol Nutrition 0.000 description 36
239000012442 inert solvent Substances 0.000 description 35
239000000243 solution Substances 0.000 description 33
150000002170 ethers Chemical class 0.000 description 30
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
239000002585 base Substances 0.000 description 27
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 26
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 26
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 25
229910052736 halogen Inorganic materials 0.000 description 25
125000004093 cyano group Chemical group *C#N 0.000 description 22
230000002829 reductive effect Effects 0.000 description 22
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
150000002367 halogens Chemical class 0.000 description 21
125000003710 aryl alkyl group Chemical group 0.000 description 20
230000009467 reduction Effects 0.000 description 19
238000006722 reduction reaction Methods 0.000 description 19
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 18
241000238631 Hexapoda Species 0.000 description 17
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
125000003545 alkoxy group Chemical group 0.000 description 17
150000008282 halocarbons Chemical class 0.000 description 17
150000001408 amides Chemical class 0.000 description 16
125000000524 functional group Chemical group 0.000 description 16
229930195733 hydrocarbon Natural products 0.000 description 16
150000002430 hydrocarbons Chemical class 0.000 description 16
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 15
150000003839 salts Chemical class 0.000 description 15
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
150000002431 hydrogen Chemical class 0.000 description 14
230000007062 hydrolysis Effects 0.000 description 14
238000006460 hydrolysis reaction Methods 0.000 description 14
239000000843 powder Substances 0.000 description 14
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 13
125000003282 alkyl amino group Chemical group 0.000 description 13
125000004663 dialkyl amino group Chemical group 0.000 description 13
125000001072 heteroaryl group Chemical group 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
150000001340 alkali metals Chemical class 0.000 description 12
150000001412 amines Chemical class 0.000 description 12
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
229910052783 alkali metal Inorganic materials 0.000 description 11
150000001735 carboxylic acids Chemical class 0.000 description 11
FDDYTYUUDGHIAU-UHFFFAOYSA-N 8-chloro-n,n-dipropyl-1,2,3,4-tetrahydronaphthalen-2-amine Chemical compound C1=CC(Cl)=C2CC(N(CCC)CCC)CCC2=C1 FDDYTYUUDGHIAU-UHFFFAOYSA-N 0.000 description 10
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 10
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
125000004414 alkyl thio group Chemical group 0.000 description 10
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 10
239000003960 organic solvent Substances 0.000 description 10
235000015424 sodium Nutrition 0.000 description 10
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 10
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239000003795 chemical substances by application Substances 0.000 description 9
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 9
239000011734 sodium Substances 0.000 description 9
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KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 8
150000008064 anhydrides Chemical class 0.000 description 8
150000002500 ions Chemical class 0.000 description 8
239000012280 lithium aluminium hydride Substances 0.000 description 8
239000003208 petroleum Substances 0.000 description 8
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239000008096 xylene Substances 0.000 description 8
241001465754 Metazoa Species 0.000 description 7
235000011054 acetic acid Nutrition 0.000 description 7
229910000288 alkali metal carbonate Inorganic materials 0.000 description 7
150000008041 alkali metal carbonates Chemical class 0.000 description 7
230000008859 change Effects 0.000 description 7
238000004587 chromatography analysis Methods 0.000 description 7
125000000753 cycloalkyl group Chemical group 0.000 description 7
230000032050 esterification Effects 0.000 description 7
238000005886 esterification reaction Methods 0.000 description 7
238000011835 investigation Methods 0.000 description 7
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
229910000029 sodium carbonate Inorganic materials 0.000 description 7
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
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125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 6
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 6
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 6
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
150000003018 phosphorus compounds Chemical class 0.000 description 6
229910000027 potassium carbonate Inorganic materials 0.000 description 6
235000011181 potassium carbonates Nutrition 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
235000017550 sodium carbonate Nutrition 0.000 description 6
SODWJACROGQSMM-UHFFFAOYSA-N 5,6,7,8-tetrahydronaphthalen-1-amine Chemical class C1CCCC2=C1C=CC=C2N SODWJACROGQSMM-UHFFFAOYSA-N 0.000 description 5
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 5
125000004453 alkoxycarbonyl group Chemical group 0.000 description 5
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
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239000003153 chemical reaction reagent Substances 0.000 description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
238000000605 extraction Methods 0.000 description 5
239000005457 ice water Substances 0.000 description 5
239000012948 isocyanate Substances 0.000 description 5
150000002513 isocyanates Chemical class 0.000 description 5
230000001665 lethal effect Effects 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
201000002266 mite infestation Diseases 0.000 description 5
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 5
NDCJIWUGZHTHAE-UHFFFAOYSA-N n-(5,6,7,8-tetrahydronaphthalen-1-yl)formamide Chemical class C1CCCC2=C1C=CC=C2NC=O NDCJIWUGZHTHAE-UHFFFAOYSA-N 0.000 description 5
239000000377 silicon dioxide Substances 0.000 description 5
239000000454 talc Substances 0.000 description 5
235000012222 talc Nutrition 0.000 description 5
229910052623 talc Inorganic materials 0.000 description 5
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 5
CXBDYQVECUFKRK-UHFFFAOYSA-N 1-methoxybutane Chemical compound CCCCOC CXBDYQVECUFKRK-UHFFFAOYSA-N 0.000 description 4
GNACAIQZXUOEEU-UHFFFAOYSA-N 3-(3-ethoxy-2-fluoro-3-oxoprop-1-enyl)-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CCOC(=O)C(F)=CC1C(C(O)=O)C1(C)C GNACAIQZXUOEEU-UHFFFAOYSA-N 0.000 description 4
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 4
QBASZPWVSZNRCW-UHFFFAOYSA-N 8-amino-5,6,7,8-tetrahydronaphthalene-1-carbonitrile Chemical compound C1=CC(C#N)=C2C(N)CCCC2=C1 QBASZPWVSZNRCW-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
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LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
229910000272 alkali metal oxide Inorganic materials 0.000 description 4
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 4
125000004104 aryloxy group Chemical group 0.000 description 4
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229910001863 barium hydroxide Inorganic materials 0.000 description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
229910052794 bromium Inorganic materials 0.000 description 4
150000004651 carbonic acid esters Chemical class 0.000 description 4
150000001733 carboxylic acid esters Chemical class 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
238000002425 crystallisation Methods 0.000 description 4
230000008025 crystallization Effects 0.000 description 4
239000003480 eluent Substances 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
150000004678 hydrides Chemical class 0.000 description 4
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
229910000041 hydrogen chloride Inorganic materials 0.000 description 4
239000007788 liquid Substances 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
229910052987 metal hydride Inorganic materials 0.000 description 4
125000004433 nitrogen atom Chemical group N* 0.000 description 4
231100000252 nontoxic Toxicity 0.000 description 4
230000003000 nontoxic effect Effects 0.000 description 4
239000003921 oil Substances 0.000 description 4
235000019198 oils Nutrition 0.000 description 4
150000002900 organolithium compounds Chemical class 0.000 description 4
230000003647 oxidation Effects 0.000 description 4
238000007254 oxidation reaction Methods 0.000 description 4
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239000012071 phase Substances 0.000 description 4
229960005235 piperonyl butoxide Drugs 0.000 description 4
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
239000012279 sodium borohydride Substances 0.000 description 4
229910000033 sodium borohydride Inorganic materials 0.000 description 4
239000000725 suspension Substances 0.000 description 4
238000010626 work up procedure Methods 0.000 description 4
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C69/743—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring of acids with a three-membered ring and with unsaturation outside the ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid 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
- 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
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/10—Oxygen atoms
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L22/00—Testing or measuring during manufacture or treatment; Reliability measurements, i.e. testing of parts without further processing to modify the parts as such; Structural arrangements therefor
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L27/00—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate

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Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Life Sciences & Earth Sciences (AREA)
Power Engineering (AREA)
Environmental Sciences (AREA)
Agronomy & Crop Science (AREA)
Plant Pathology (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Pest Control & Pesticides (AREA)
Microelectronics & Electronic Packaging (AREA)
Computer Hardware Design (AREA)
Health & Medical Sciences (AREA)
General Physics & Mathematics (AREA)
Condensed Matter Physics & Semiconductors (AREA)
Physics & Mathematics (AREA)
Manufacturing & Machinery (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

DD88312674A 1987-02-06 1988-02-04 Verfahren zur herstellung neuer cyclopropancarbonsaeureester DD280097A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR8701458A FR2610624B1 (fr)	1987-02-06	1987-02-06	Nouveaux esters d'acides cyclopropanecarboxyliques apparentes a l'acide pyrethrique, leur procede de preparation et leur application a la lutte contre les parasites

Publications (1)

Publication Number	Publication Date
DD280097A5 true DD280097A5 (de)	1990-06-27

Family

ID=9347652

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD88312674A DD280097A5 (de)	1987-02-06	1988-02-04	Verfahren zur herstellung neuer cyclopropancarbonsaeureester

Country Status (23)

Country	Link
US (1)	US4939172A (pt)
EP (1)	EP0281439B1 (pt)
JP (1)	JPH0729989B2 (pt)
KR (1)	KR960005514B1 (pt)
AT (1)	ATE64368T1 (pt)
AU (1)	AU601808B2 (pt)
BR (1)	BR8800473A (pt)
CA (1)	CA1325013C (pt)
DD (1)	DD280097A5 (pt)
DE (1)	DE3863202D1 (pt)
DK (1)	DK58288A (pt)
EG (1)	EG18663A (pt)
ES (1)	ES2022993B3 (pt)
FR (1)	FR2610624B1 (pt)
GR (1)	GR3002415T3 (pt)
HU (1)	HU204668B (pt)
IL (1)	IL85315A (pt)
MX (1)	MX10309A (pt)
NZ (1)	NZ223411A (pt)
OA (1)	OA08806A (pt)
PT (1)	PT86708B (pt)
SU (1)	SU1746881A3 (pt)
ZA (1)	ZA88822B (pt)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0302626A3 (en) *	1987-08-06	1989-12-13	Imperial Chemical Industries Plc	Insecticidal compounds
GB8902324D0 (en) *	1989-02-02	1989-03-22	Ici Plc	Insecticidal compounds
FR2678609B1 (fr) *	1991-07-04	1994-08-26	Roussel Uclaf	Nouveaux esters pyrethrinouides de l'alcool 4-amino 2,3,5,6-tetrafluorophenyl methylique, leur procede de preparation et leur application comme pesticides.
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.
FR2693191B1 (fr) *	1992-07-01	1994-08-26	Roussel Uclaf	Nouvel ester de l'acide [1R[1alpha,3beta(Z)]] 2,2-diméthyl 3-(2-fluoro 3-méthoxy 3-oxo propényl) cyclopropane carboxylique, son procédé de préparation et son application comme pesticide.
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.
DE69618096T2 (de) *	1995-02-07	2002-07-18	Dainihon Jochugiku Co., Ltd.	Neue carbonsäure-derivate, verfahren zur herstellung und diese verbindungen enthaltende insektizide
US6358883B1 (en) *	1998-11-16	2002-03-19	American Cyanamid Company	Pesticidal and parasiticidal use of 1-aryl-1-(substituted thio, sulfinyl and sulfonyl)-2-nitroethane compounds
JP3991812B2 (ja) *	2001-12-11	2007-10-17	住友化学株式会社	エステル化合物およびその用途
JP2004143151A (ja) *	2002-10-02	2004-05-20	Dainippon Jochugiku Co Ltd	ハエ取り線香
US20050113581A1 (en) *	2003-11-26	2005-05-26	Sumitomo Chemical Company, Limited	Process for the preparation of carboxylic acid esters
JP4488765B2 (ja) *	2004-02-26	2010-06-23	大日本除蟲菊株式会社	エアゾール殺虫剤
TW200716517A (en) *	2005-04-29	2007-05-01	Wyeth Corp	Process for preparing 3,3-disubstituted oxindoles and thio-oxindoles
AU2007250934B2 (en)	2006-05-11	2012-02-09	Sumitomo Chemical Company, Limited	Ester compound and its use in pest control
JP5076623B2 (ja) *	2006-05-11	2012-11-21	住友化学株式会社	エステル化合物及びその有害生物防除用途
CN108178716B (zh) *	2017-11-21	2021-06-01	成都大学	一种具有多取代基的手性环丙烷化合物及其合成方法
CN108084054B (zh) *	2017-11-21	2020-08-07	成都大学	一种多取代手性烯基环丙烷化合物及其晶体和其制备方法与用途

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB2066810A (en) *	1979-12-21	1981-07-15	Ici Ltd	Fluorinated benzyl esters of cyclopropane carboxylic acids
US4370346A (en) *	1979-12-21	1983-01-25	Imperial Chemical Industries Plc	Halogenated esters
WO1981002892A1 (en) *	1980-04-10	1981-10-15	Dainippon Jochugiku Kk	Cyclopropanecarboxylic acid ester derivatives,process for their preparation,and insecticidal and acaricidal composition containing such as effective ingredients
OA06786A (fr) *	1980-04-16	1982-12-31	Roussel Uclaf	Nouveaux dérivés de l'acide cyclopropane, leur préparation, leur application à la lutte contre les parasites des végétaux et des animaux, les compositions les renfermant et les nouveaux intermediaires obtenus.
FR2482955A1 (fr) *	1980-05-23	1981-11-27	Roussel Uclaf	Nouveaux derives de l'acide cyclopropane carboxylique, leur procede de preparation et leur application a la lutte contre les parasites
FR2486073A1 (fr) *	1980-07-02	1982-01-08	Roussel Uclaf	Nouveaux derives de l'acide cyclopropane carboxylique, leur procede de preparation, et leur application a la lutte contre les parasites
AU543390B2 (en) *	1980-07-18	1985-04-18	Commonwealth Scientific And Industrial Research Organisation	Pentafluorobenzyl esters of pyrethroid type insecticides
FR2491060A1 (fr) *	1980-10-01	1982-04-02	Roussel Uclaf	Esters d'acides cyclopropanes carboxyliques apparentes a l'acide pyrethrique, leur procede de preparation et leur application a la lutte contre les parasites
US4489093A (en) *	1980-10-01	1984-12-18	Roussel Uclaf	Insecticidal esters
GB8505819D0 (en) *	1985-03-06	1985-04-11	Ici Plc	Fluorobenzyl esters
GB8522656D0 (en) *	1985-09-13	1985-10-16	Ici Plc	Fluoro alcohols
GB8629806D0 (en) *	1986-12-12	1987-01-21	Ici Plc	Fluorobenzyl esters

1987
- 1987-02-06 FR FR8701458A patent/FR2610624B1/fr not_active Expired
1988
- 1988-02-02 EP EP88400240A patent/EP0281439B1/fr not_active Expired - Lifetime
- 1988-02-02 ES ES88400240T patent/ES2022993B3/es not_active Expired - Lifetime
- 1988-02-02 AT AT88400240T patent/ATE64368T1/de not_active IP Right Cessation
- 1988-02-02 DE DE8888400240T patent/DE3863202D1/de not_active Expired - Lifetime
- 1988-02-03 JP JP63022155A patent/JPH0729989B2/ja not_active Expired - Lifetime
- 1988-02-03 MX MX1030988A patent/MX10309A/es unknown
- 1988-02-04 DD DD88312674A patent/DD280097A5/de not_active IP Right Cessation
- 1988-02-04 IL IL85315A patent/IL85315A/xx not_active IP Right Cessation
- 1988-02-04 NZ NZ223411A patent/NZ223411A/xx unknown
- 1988-02-04 EG EG59/88A patent/EG18663A/xx active
- 1988-02-04 SU SU884355520A patent/SU1746881A3/ru active
- 1988-02-05 CA CA000558326A patent/CA1325013C/fr not_active Expired - Fee Related
- 1988-02-05 BR BR8800473A patent/BR8800473A/pt not_active IP Right Cessation
- 1988-02-05 HU HU88545A patent/HU204668B/hu unknown
- 1988-02-05 DK DK058288A patent/DK58288A/da not_active Application Discontinuation
- 1988-02-05 ZA ZA88822A patent/ZA88822B/xx unknown
- 1988-02-05 AU AU11344/88A patent/AU601808B2/en not_active Ceased
- 1988-02-05 PT PT86708A patent/PT86708B/pt not_active IP Right Cessation
- 1988-02-05 OA OA59277A patent/OA08806A/xx unknown
- 1988-02-06 KR KR1019880001160A patent/KR960005514B1/ko not_active IP Right Cessation
- 1988-02-08 US US07/153,157 patent/US4939172A/en not_active Expired - Lifetime
1991
- 1991-08-02 GR GR90401169T patent/GR3002415T3/el unknown

Also Published As

Publication number	Publication date
EG18663A (fr)	1993-10-30
CA1325013C (fr)	1993-12-07
HUT47211A (en)	1989-02-28
BR8800473A (pt)	1988-09-20
KR880009901A (ko)	1988-10-05
ATE64368T1 (de)	1991-06-15
IL85315A0 (en)	1988-07-31
JPS63201146A (ja)	1988-08-19
DK58288D0 (da)	1988-02-05
JPH0729989B2 (ja)	1995-04-05
PT86708A (pt)	1988-03-01
ZA88822B (en)	1989-04-26
SU1746881A3 (ru)	1992-07-07
GR3002415T3 (en)	1992-12-30
PT86708B (pt)	1992-04-30
HU204668B (en)	1992-02-28
US4939172A (en)	1990-07-03
FR2610624B1 (fr)	1989-06-09
IL85315A (en)	1992-07-15
KR960005514B1 (ko)	1996-04-25
DK58288A (da)	1988-08-07
AU1134488A (en)	1988-08-11
NZ223411A (en)	1990-02-26
OA08806A (fr)	1989-03-31
EP0281439A1 (fr)	1988-09-07
AU601808B2 (en)	1990-09-20
DE3863202D1 (de)	1991-07-18
EP0281439B1 (fr)	1991-06-12
MX10309A (es)	1993-11-01
ES2022993B3 (es)	1991-12-16
FR2610624A1 (fr)	1988-08-12

Legal Events

Date	Code	Title	Description
1996-01-18	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DD280097A5 (de)	1990-06-27	Verfahren zur herstellung neuer cyclopropancarbonsaeureester
EP0005848B1 (de)	1981-12-30	N-Alkylierte Aminoalkohole und ihre Salze, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Präparate
EP0400011B1 (de)	1994-01-26	Neue phenylethanolamine
DE2915037A1 (de)	1979-11-08	Neue n-substituierte moranolinderivate
DE19520936A1 (de)	1996-12-12	Ektoparasitizide Mittel
DE2709264B2 (de)	1981-05-07	Substituierte Phenoxybenzyloxycarbonylderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide und Akarizide sowie neue Zwischenprodukte
DE2525133A1 (de)	1975-12-18	Alkanolaminderivate
EP0740666B1 (de)	1999-11-10	Substituierte 1,2,3,4-tetrahydro-5-nitro-pyrimidine
EP0079311B1 (de)	1987-03-18	Phenylbenzoylharnstoffe zur Bekämpfung von Schädlingen
DE2615435C2 (de)	1984-02-09	Substituierte Phenoxybenzyloxycarbonylderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide und Akarizide
EP0320448B1 (de)	1994-12-28	3-Aminobenzoylphenylharnstoffe
DD140194A5 (de)	1980-02-20	Insektizide und akarizide mittel
DE2745222A1 (de)	1978-04-20	Alkanolaminderivate
DE68905171T2 (de)	1993-06-17	Benzol-derivate, ihre herstellung und pharmazeutische zusammensetzungen, die diese enthalten.
DE1667979A1 (de)	1971-07-15	Schaedlingsbekaempfungsmittel,die bestimmte Benzodioxole enthalten,sowie Verfahren zu deren Herstellung
DE69301675T2 (de)	1996-09-19	Derivate der 7-Äthynyl-Alpha-(Methoxymethylen)1-naphthylessigsäure, ihr Herstellungsverfahren und ihre Anwendung als Pesticide
DE3627663A1 (de)	1988-03-03	Heteroarylethylamine, verfahren zu ihrer herstellung und ihre verwendung als leistungsfoerderer bei tieren
DE68924786T2 (de)	1996-04-18	(Trifluormethyl)vinylpyrethroidderivate, ihre Verwendung als Pestizide, Verfahren zu ihrer Herstellung und Zwischenprodukte dieses Verfahrens.
DE69304099T2 (de)	1997-01-23	Von 6-Trifluoromethylbenzylalkohol abgeleitete Pyrethrinoidester, Verfahren zu ihrer Herstellung und ihre Anwendung als Pestizide
DE69417969T2 (de)	1999-09-30	Von 6-Trifluoromethylbenzylalkohol abgeleitete Pyrethrinoidester, Verfahren zu ihrer Herstellung und ihre Anwendung als Pestizide
DE69724216T2 (de)	2004-06-24	Pyridin-Zwischenprodukte, verwendbar zur Herstellung von Beta-adrenergischen Rezeptor-Agonisten
DE69210639T2 (de)	1996-10-24	3-(3,3,3-Trifluor-2-Chlorpropenyl)-2,2-Dimethylcyclopropancarbonsäureester, Verfahren zu ihrer Herstellung und ihre Verwendung als Pestitzide
DE2936864A1 (de)	1981-04-02	(+-)-trans-3-(e, z-2-chlor-2-(4-chlorphenyl)-vinyl)-, 2,2-dimethyl-cyclopropan-carbonsaeure-(+-)-(alpha)-cyano-3-phenoxy-4-fluor-benzyl)-ester, die einzelnen e- und z-isomeren, verfahren zur herstellung dieser verbindungen und ihre verwendung als ektoparasitizide
EP0388739A1 (de)	1990-09-26	Tetrahydronaphtalinderivate
EP0375613A2 (de)	1990-06-27	Nitroenamine