DE3239200A1 - Neue ester aromatischer oder heteroaromatischer alkohole, deren herstellungsverfahren und herstellungszwischenprodukte, deren verwendung bei der bekaempfung von parasiten und die sie enthaltenden zusammensetzungen - Google Patents

Neue ester aromatischer oder heteroaromatischer alkohole, deren herstellungsverfahren und herstellungszwischenprodukte, deren verwendung bei der bekaempfung von parasiten und die sie enthaltenden zusammensetzungen

Info

Publication number: DE3239200A1
Authority: DE; Germany
Prior art keywords: formula; compounds; alcohol; radical; atom
Prior art date: 1981-10-23
Legal status (The legal status 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 Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Withdrawn

Application number

DE19823239200

Other languages

German (de)

English (en)

Inventor

Jean-Pierre 93100 Montreuil-sous-Bois Demoute

Jean 94300 Vincennes Tessier

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Sanofi Aventis France

Original Assignee

Roussel Uclaf SA

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.)

1981-10-23

Filing date

1982-10-22

Publication date

1983-05-11

1982-10-22 Application filed by Roussel Uclaf SA filed Critical Roussel Uclaf SA

1983-05-11 Publication of DE3239200A1 publication Critical patent/DE3239200A1/de

Status Withdrawn legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims description 56
150000001298 alcohols Chemical class 0.000 title claims description 21
244000045947 parasite Species 0.000 title claims description 14
238000004519 manufacturing process Methods 0.000 title description 18
239000013067 intermediate product Substances 0.000 title 1
-1 heteroaromatic radical Chemical class 0.000 claims description 69
150000001875 compounds Chemical class 0.000 claims description 62
125000005843 halogen group Chemical group 0.000 claims description 28
150000002148 esters Chemical class 0.000 claims description 26
239000000460 chlorine Substances 0.000 claims description 25
238000000034 method Methods 0.000 claims description 25
239000004480 active ingredient Substances 0.000 claims description 20
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 19
239000002253 acid Substances 0.000 claims description 17
125000004432 carbon atom Chemical group C* 0.000 claims description 17
150000003254 radicals Chemical class 0.000 claims description 15
241001465754 Metazoa Species 0.000 claims description 12
229910052731 fluorine Inorganic materials 0.000 claims description 12
229910052801 chlorine Inorganic materials 0.000 claims description 11
239000003814 drug Substances 0.000 claims description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N methyl alcohol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 10
241000196324 Embryophyta Species 0.000 claims description 9
230000000895 acaricidal effect Effects 0.000 claims description 9
125000003118 aryl group Chemical group 0.000 claims description 9
239000011737 fluorine Substances 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
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 7
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 6
125000000524 functional group Chemical group 0.000 claims description 6
230000000749 insecticidal effect Effects 0.000 claims description 6
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 6
125000004430 oxygen atom Chemical group O* 0.000 claims description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
125000001153 fluoro group Chemical group F* 0.000 claims description 5
230000001069 nematicidal effect Effects 0.000 claims description 5
229910052717 sulfur Chemical group 0.000 claims description 5
125000004434 sulfur atom Chemical group 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
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
235000019728 animal nutrition Nutrition 0.000 claims description 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 3
125000001174 sulfone group Chemical group 0.000 claims description 3
125000003375 sulfoxide group Chemical group 0.000 claims description 3
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
235000007516 Chrysanthemum Nutrition 0.000 claims description 2
244000189548 Chrysanthemum x morifolium Species 0.000 claims description 2
230000002378 acidificating effect Effects 0.000 claims description 2
150000007513 acids Chemical class 0.000 claims description 2
230000000855 fungicidal effect Effects 0.000 claims description 2
150000002576 ketones Chemical class 0.000 claims description 2
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims description 2
229920006395 saturated elastomer Polymers 0.000 claims description 2
229910014033 C-OH Inorganic materials 0.000 claims 1
229910014570 C—OH Inorganic materials 0.000 claims 1
YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 claims 1
125000000623 heterocyclic group Chemical group 0.000 claims 1
229940011051 isopropyl acetate Drugs 0.000 claims 1
239000000047 product Substances 0.000 description 60
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 48
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 41
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 29
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 20
239000000243 solution Substances 0.000 description 19
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 16
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
239000000377 silicon dioxide Substances 0.000 description 14
238000004458 analytical method Methods 0.000 description 11
241000238631 Hexapoda Species 0.000 description 10
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
239000003208 petroleum Substances 0.000 description 9
239000000843 powder Substances 0.000 description 9
238000003756 stirring Methods 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
241000238876 Acari Species 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 6
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 6
239000012074 organic phase Substances 0.000 description 6
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 5
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 5
235000011054 acetic acid Nutrition 0.000 description 5
239000000543 intermediate Substances 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
239000002904 solvent Substances 0.000 description 5
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
230000000694 effects Effects 0.000 description 4
238000005886 esterification reaction Methods 0.000 description 4
NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
239000008096 xylene Substances 0.000 description 4
OPLCSTZDXXUYDU-UHFFFAOYSA-N 2,4-dimethyl-6-tert-butylphenol Chemical compound CC1=CC(C)=C(O)C(C(C)(C)C)=C1 OPLCSTZDXXUYDU-UHFFFAOYSA-N 0.000 description 3
206010063409 Acarodermatitis Diseases 0.000 description 3
241000238657 Blattella germanica Species 0.000 description 3
FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
241000255925 Diptera Species 0.000 description 3
241000257159 Musca domestica Species 0.000 description 3
241000244206 Nematoda Species 0.000 description 3
241000509427 Sarcoptes scabiei Species 0.000 description 3
239000003638 chemical reducing agent Substances 0.000 description 3
230000032050 esterification Effects 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
150000002367 halogens Chemical class 0.000 description 3
239000007788 liquid Substances 0.000 description 3
230000003071 parasitic effect Effects 0.000 description 3
229960005235 piperonyl butoxide Drugs 0.000 description 3
238000010992 reflux Methods 0.000 description 3
208000005687 scabies Diseases 0.000 description 3
235000012239 silicon dioxide Nutrition 0.000 description 3
239000012279 sodium borohydride Substances 0.000 description 3
229910000033 sodium borohydride Inorganic materials 0.000 description 3
239000000126 substance Substances 0.000 description 3
MRLGCTNJRREZHZ-UHFFFAOYSA-N 3-phenoxybenzaldehyde Chemical compound O=CC1=CC=CC(OC=2C=CC=CC=2)=C1 MRLGCTNJRREZHZ-UHFFFAOYSA-N 0.000 description 2
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
241001481703 Rhipicephalus <genus> Species 0.000 description 2
241000447727 Scabies Species 0.000 description 2
241001454293 Tetranychus urticae Species 0.000 description 2
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
125000001246 bromo group Chemical group Br* 0.000 description 2
DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 2
230000001680 brushing effect Effects 0.000 description 2
235000013339 cereals Nutrition 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
238000010410 dusting Methods 0.000 description 2
239000004495 emulsifiable concentrate Substances 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
235000013305 food Nutrition 0.000 description 2
238000003197 gene knockdown Methods 0.000 description 2
239000008187 granular material Substances 0.000 description 2
239000008240 homogeneous mixture Substances 0.000 description 2
238000011835 investigation Methods 0.000 description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
235000015097 nutrients Nutrition 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
239000012071 phase Substances 0.000 description 2
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
229920000053 polysorbate 80 Polymers 0.000 description 2
235000003270 potassium fluoride Nutrition 0.000 description 2
239000011698 potassium fluoride Substances 0.000 description 2
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
239000011734 sodium Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 2
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MZONOPSOHSEQMN-UHFFFAOYSA-N 2,2-dibromoethenyl cyclopropanecarboxylate Chemical compound BrC(Br)=COC(=O)C1CC1 MZONOPSOHSEQMN-UHFFFAOYSA-N 0.000 description 1
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 description 1
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BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 1
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CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
240000004460 Tanacetum coccineum Species 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
ROVGZAWFACYCSP-MQBLHHJJSA-N [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 Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OC1C(C)=C(C\C=C/C=C)C(=O)C1 ROVGZAWFACYCSP-MQBLHHJJSA-N 0.000 description 1
XIPUIGPNIDKXJU-UHFFFAOYSA-N [CH]1CC1 Chemical compound [CH]1CC1 XIPUIGPNIDKXJU-UHFFFAOYSA-N 0.000 description 1
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DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
239000003905 agrochemical Substances 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
239000010775 animal oil Substances 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
125000005129 aryl carbonyl group Chemical group 0.000 description 1
125000005002 aryl methyl group Chemical group 0.000 description 1
125000004391 aryl sulfonyl group Chemical group 0.000 description 1
125000005110 aryl thio group Chemical group 0.000 description 1
125000004104 aryloxy group Chemical group 0.000 description 1
238000000889 atomisation Methods 0.000 description 1
239000002585 base Substances 0.000 description 1
238000003287 bathing Methods 0.000 description 1
150000001555 benzenes Chemical class 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
229960001506 brilliant green Drugs 0.000 description 1
HXCILVUBKWANLN-UHFFFAOYSA-N brilliant green cation Chemical compound C1=CC(N(CC)CC)=CC=C1C(C=1C=CC=CC=1)=C1C=CC(=[N+](CC)CC)C=C1 HXCILVUBKWANLN-UHFFFAOYSA-N 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
229950005228 bromoform Drugs 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
210000000038 chest Anatomy 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
230000001079 digestive effect Effects 0.000 description 1
BGRWYRAHAFMIBJ-UHFFFAOYSA-N diisopropylcarbodiimide Natural products CC(C)NC(=O)NC(C)C BGRWYRAHAFMIBJ-UHFFFAOYSA-N 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000004467 fishmeal Substances 0.000 description 1
235000013312 flour Nutrition 0.000 description 1
239000011521 glass Substances 0.000 description 1
239000003630 growth substance Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
125000001072 heteroaryl group Chemical group 0.000 description 1
BXXDGLDKZGEUGZ-UHFFFAOYSA-N hex-1-enyl cyclopropanecarboxylate Chemical compound CCCCC=COC(=O)C1CC1 BXXDGLDKZGEUGZ-UHFFFAOYSA-N 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
239000005457 ice water Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
235000021190 leftovers Nutrition 0.000 description 1
229940126601 medicinal product Drugs 0.000 description 1
239000011707 mineral Chemical class 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
229910000403 monosodium phosphate Inorganic materials 0.000 description 1
235000019799 monosodium phosphate Nutrition 0.000 description 1
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000002736 nonionic surfactant Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
235000020232 peanut Nutrition 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
239000004540 pour-on Substances 0.000 description 1
230000003449 preventive effect Effects 0.000 description 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
238000000746 purification Methods 0.000 description 1
229940015367 pyrethrum Drugs 0.000 description 1
230000000384 rearing effect Effects 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000007790 scraping Methods 0.000 description 1
230000035939 shock Effects 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
230000000391 smoking effect Effects 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
239000002689 soil Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000004550 soluble concentrate Substances 0.000 description 1
238000005507 spraying Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
235000013343 vitamin Nutrition 0.000 description 1
239000011782 vitamin Substances 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
229930003231 vitamin Natural products 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids

Landscapes

Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Chemical & Material Sciences (AREA)
Public Health (AREA)
Emergency Medicine (AREA)
Pest Control & Pesticides (AREA)
Agronomy & Crop Science (AREA)
Plant Pathology (AREA)
Engineering & Computer Science (AREA)
Dentistry (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)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

DE19823239200 1981-10-23 1982-10-22 Neue ester aromatischer oder heteroaromatischer alkohole, deren herstellungsverfahren und herstellungszwischenprodukte, deren verwendung bei der bekaempfung von parasiten und die sie enthaltenden zusammensetzungen Withdrawn DE3239200A1 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR8119944A FR2515176A1 (fr)	1981-10-23	1981-10-23	Nouveaux esters d'alcools aromatiques ou heteroaromatiques, leur procede de preparation et leur application a la lutte contre les parasites

Publications (1)

Publication Number	Publication Date
DE3239200A1 true DE3239200A1 (de)	1983-05-11

Family

ID=9263335

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DE19823239200 Withdrawn DE3239200A1 (de)	1981-10-23	1982-10-22	Neue ester aromatischer oder heteroaromatischer alkohole, deren herstellungsverfahren und herstellungszwischenprodukte, deren verwendung bei der bekaempfung von parasiten und die sie enthaltenden zusammensetzungen

Country Status (7)

Country	Link
JP (1)	JPS5879955A (fr)
CH (1)	CH655302A5 (fr)
DE (1)	DE3239200A1 (fr)
FR (1)	FR2515176A1 (fr)
GB (1)	GB2108123A (fr)
IT (1)	IT1158023B (fr)
NL (1)	NL8204049A (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4694013A (en) *	1985-11-08	1987-09-15	E. I. Du Pont De Nemours And Company	Insecticidal and acaricidal phenoxypyrdinyl esters and intermediates
GB8617649D0 (en) *	1986-07-18	1986-08-28	Ici Plc	Fluorobenzyl esters

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4152455A (en) *	1977-02-02	1979-05-01	Fmc Corporation	Insecticidal α-trifluoromethyl-3-phenoxybenzyl carboxylates
US4431668A (en) *	1977-12-01	1984-02-14	Dainippon Jochugiku Kabushiki Kaisha	Cyclopropane carboxylic acid ester derivatives
IN150399B (fr) *	1978-01-20	1982-09-25	Fmc Corp
US4200644A (en) *	1978-01-26	1980-04-29	Fmc Corporation	Arylthiovinylcyclopropanecarboxylate insecticides
JPS5581836A (en) *	1978-12-13	1980-06-20	Yoshio Katsuta	Derivative of cyclopropanecarboxylic acid ester, its preparation and insecticide containing the same
JPS5620547A (en) *	1979-07-31	1981-02-26	Yoshio Katsuta	Cyclopropanecarboxylic ester derivative, its preparation, and insecticide comprising the same
JPS5646843A (en) *	1979-09-23	1981-04-28	Yoshio Katsuta	Novel carboxylic acid ester derivative, preparation of novel carboxylic acid ester derivative, and insecticide containing novel carboxylic acid ester derivative
JPS56115741A (en) *	1980-02-16	1981-09-11	Yoshio Katsuta	Cyclopropanecarboxylic acid ester derivative, preparation of cyclopropanecarboxylic acid ester derivative, and insecticide containing cyclopropanecarboxylic acid ester derivative

1981
- 1981-10-23 FR FR8119944A patent/FR2515176A1/fr active Granted
1982
- 1982-10-20 NL NL8204049A patent/NL8204049A/nl not_active Application Discontinuation
- 1982-10-22 CH CH6165/82A patent/CH655302A5/fr not_active IP Right Cessation
- 1982-10-22 DE DE19823239200 patent/DE3239200A1/de not_active Withdrawn
- 1982-10-22 IT IT49340/82A patent/IT1158023B/it active
- 1982-10-22 GB GB08230153A patent/GB2108123A/en not_active Withdrawn
- 1982-10-22 JP JP57184813A patent/JPS5879955A/ja active Pending

Also Published As

Publication number	Publication date
FR2515176A1 (fr)	1983-04-29
CH655302A5 (fr)	1986-04-15
IT8249340A0 (it)	1982-10-22
JPS5879955A (ja)	1983-05-13
GB2108123A (en)	1983-05-11
NL8204049A (nl)	1983-05-16
IT1158023B (it)	1987-02-18
FR2515176B1 (fr)	1984-09-28

Legal Events

Date	Code	Title	Description
1987-10-15	8139	Disposal/non-payment of the annual fee

Publication	Publication Date	Title
DE2653189A1 (de)	1977-06-08	Cyclopropanverbindungen, verfahren zu ihrer herstellung und diese verbindungen enthaltende insektizide
JPS6254421B2 (fr)	1987-11-14
JPS6224418B2 (fr)	1987-05-28
DE2327660B2 (de)	1977-10-27	Cyclopropancarbonsaeureester, verfahren zu ihrer herstellung und ihre verwendung als insektizide
US4602038A (en)	1986-07-22	Insecticidal cyclopropane carboxylates
JPH0625205A (ja)	1994-02-01	フラン又はチオフェンアルコールから誘導される新規なピレスロイドエステル、それらの製造法及び有害生物駆除剤としての用途
DE68906992T2 (de)	1993-11-11	Indanylring enthaltende pyrethinester, deren herstellung und deren anwendung als pestizide.
DE3781092T2 (de)	1993-03-18	Aethylenische oximderivate von cyclopropancarbonsaeureestern, verfahren und zwischenprodukte zu ihrer herstellung und ihre verwendung zur bekaempfung von parasiten.
US4565822A (en)	1986-01-21	2-Fluoro-2-cyanoethenyl cyclopropane carboxylates as pesticides
DD148767A5 (de)	1981-06-10	Verfahren zur herstellung insektizider und acarizider verbindungen
DE3781383T2 (de)	1993-03-04	2,2-dimethylcyclopropancarbonsaeurederivate, die eine gesaettigte halogenierte kette an c-3 tragen, verfahren und zwischenprodukte zu ihrer herstellung, ihre verwendung als pestizide und sie enthaltende zusammensetzungen.
DE2903268A1 (de)	1979-09-27	Neue ester von cyclopropancarbonsaeuren mit einem polyhalogenierten substituenten, verfahren zu deren herstellung und pestizide zusammensetzungen
DE3126327C2 (fr)	1991-11-14
DE3214076A1 (de)	1982-11-18	Neue cyclopropancarbonsaeurederivate, deren herstellung, deren verwendung bei der bekaempfung von parasiten und die sie enthaltenden zusammensetzungen
DE3239200A1 (de)	1983-05-11	Neue ester aromatischer oder heteroaromatischer alkohole, deren herstellungsverfahren und herstellungszwischenprodukte, deren verwendung bei der bekaempfung von parasiten und die sie enthaltenden zusammensetzungen
DE1961155A1 (de)	1970-07-02	Synthetische Pyrethroide und ihre Verwendung als Insecticide
US5530022A (en)	1996-06-25	Esters of 2,2-dimethyl-3-(3,3,3-trifluoro-1-propenyl)-cyclopropane carboxylic acid
JP3269854B2 (ja)	2002-04-02	１，３，４，５，６，７−ヘキサヒドロ−１，３−ジオキソ−２ｈ−イソインドール−２−イルメチルアルコールの新規なピレスリノイドエステル、それらの製造法及びそれらのペスチサイドとしての用途
US4920231A (en)	1990-04-24	Process of braking triflouromethyl compounds
JPH0641015A (ja)	1994-02-15	６−（トリフルオルメチル）ベンジルアルコールから誘導される新規なピレスリノイドエステル、それらの製造法及びそれらの有害生物駆除剤としての用途
DE3138063C2 (fr)	1989-08-31
JP3320453B2 (ja)	2002-09-03	４−アミノ−２，３，５，６−テトラフルオルフェニルメチルアルコールの新規なピレスリノイドエステル、それらの製造法及びそれらのペスチサイドとしての用途
DD149895A5 (de)	1981-08-05	Insektizide mittel
DE3207009A1 (de)	1982-09-16	Ester heterocyclischer sich von thiazol oder thiadiazol ableitender alkohole, deren herstellungsverfahren und die sie enthaltenden pestiziden zusammensetzungen
DE3879018T2 (de)	1993-09-09	Pyrethrinoid-derivate, die ein n-heteroring enthalten, verfahren und zwischenprodukte zu deren herstellung, deren anwendung als pestizide, und diese enthaltende zusammenstellungen.