OA10984A - Insect-repellent formulations - Google Patents

Insect-repellent formulations Download PDF

Info

Publication number: OA10984A
Authority: OA; OAPI
Prior art keywords: compound; formula; formulation; hexane; dione
Prior art date: 1996-09-26

Application number

OA9900043A

Other languages

English (en)

Inventor

Darren John Schulz

Original Assignee

Pfizer

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.)

1996-09-26

Filing date

1999-02-26

Publication date

2001-11-05

1999-02-26 Application filed by Pfizer filed Critical Pfizer

2001-11-05 Publication of OA10984A publication Critical patent/OA10984A/en

Links

239000000203 mixture Substances 0.000 title claims abstract description 42
238000009472 formulation Methods 0.000 title claims abstract description 21
239000000077 insect repellent Substances 0.000 title description 5
150000001875 compounds Chemical class 0.000 claims abstract description 47
229910052736 halogen Inorganic materials 0.000 claims abstract description 6
125000000217 alkyl group Chemical group 0.000 claims abstract description 5
150000002367 halogens Chemical class 0.000 claims abstract description 5
239000002671 adjuvant Substances 0.000 claims abstract description 4
239000003085 diluting agent Substances 0.000 claims abstract description 4
125000000304 alkynyl group Chemical group 0.000 claims abstract description 3
239000005871 repellent Substances 0.000 claims abstract description 3
-1 6-hepten-1-yl Chemical group 0.000 claims description 16
238000000034 method Methods 0.000 claims description 16
229910052740 iodine Inorganic materials 0.000 claims description 7
241000255925 Diptera Species 0.000 claims description 6
239000006071 cream Substances 0.000 claims description 6
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 6
241000238631 Hexapoda Species 0.000 claims description 5
241000124008 Mammalia Species 0.000 claims description 5
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 5
241000238876 Acari Species 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
239000000460 chlorine Substances 0.000 claims description 4
101100037762 Caenorhabditis elegans rnh-2 gene Proteins 0.000 claims description 3
125000003342 alkenyl group Chemical group 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
241000255930 Chironomidae Species 0.000 claims description 2
241001465754 Metazoa Species 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
125000004043 oxo group Chemical group O=* 0.000 claims description 2
230000001846 repelling effect Effects 0.000 claims description 2
SGPGESCZOCHFCL-UHFFFAOYSA-N Tilisolol hydrochloride Chemical compound [Cl-].C1=CC=C2C(=O)N(C)C=C(OCC(O)C[NH2+]C(C)(C)C)C2=C1 SGPGESCZOCHFCL-UHFFFAOYSA-N 0.000 claims 3
CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 claims 2
125000001309 chloro group Chemical group Cl* 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
125000006564 (C4-C8) cycloalkyl group Chemical group 0.000 abstract 1
125000006374 C2-C10 alkenyl group Chemical group 0.000 abstract 1
125000000392 cycloalkenyl group Chemical group 0.000 abstract 1
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 31
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 25
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 22
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 20
239000011541 reaction mixture Substances 0.000 description 16
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
239000004698 Polyethylene Substances 0.000 description 11
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
229910052943 magnesium sulfate Inorganic materials 0.000 description 11
235000019341 magnesium sulphate Nutrition 0.000 description 11
229920000573 polyethylene Polymers 0.000 description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
239000000284 extract Substances 0.000 description 10
229910052757 nitrogen Inorganic materials 0.000 description 10
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 9
239000012312 sodium hydride Substances 0.000 description 9
229910000104 sodium hydride Inorganic materials 0.000 description 9
229940093499 ethyl acetate Drugs 0.000 description 8
235000019439 ethyl acetate Nutrition 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 7
UHQOPDGATRGDDD-UHFFFAOYSA-N 3-azabicyclo[3.1.0]hexane-2,4-dione Chemical compound O=C1NC(=O)C2CC12 UHQOPDGATRGDDD-UHFFFAOYSA-N 0.000 description 6
238000004587 chromatography analysis Methods 0.000 description 6
239000002904 solvent Substances 0.000 description 6
238000000023 Kugelrohr distillation Methods 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
238000009835 boiling Methods 0.000 description 5
238000003786 synthesis reaction Methods 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
NDOGLIPWGGRQCO-UHFFFAOYSA-N hexane-2,4-dione Chemical compound CCC(=O)CC(C)=O NDOGLIPWGGRQCO-UHFFFAOYSA-N 0.000 description 4
239000002674 ointment Substances 0.000 description 4
239000000377 silicon dioxide Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 2
OARPPWYKZSLDTJ-UHFFFAOYSA-N 3-octyl-3-azabicyclo[3.1.0]hexane-2,4-dione Chemical compound O=C1N(CCCCCCCC)C(=O)C2CC21 OARPPWYKZSLDTJ-UHFFFAOYSA-N 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
241000282412 Homo Species 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
230000002411 adverse Effects 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
239000001569 carbon dioxide Substances 0.000 description 2
229910002092 carbon dioxide Inorganic materials 0.000 description 2
FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
230000001804 emulsifying effect Effects 0.000 description 2
FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
239000000499 gel Substances 0.000 description 2
238000000338 in vitro Methods 0.000 description 2
239000006210 lotion Substances 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
229960005323 phenoxyethanol Drugs 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000008213 purified water Substances 0.000 description 2
239000000344 soap Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
MFDSUEYHCWXFSD-UHFFFAOYSA-N 1-chloro-4-iodooctane Chemical compound CCCCC(I)CCCCl MFDSUEYHCWXFSD-UHFFFAOYSA-N 0.000 description 1
LMHCYRULPLGEEZ-UHFFFAOYSA-N 1-iodoheptane Chemical compound CCCCCCCI LMHCYRULPLGEEZ-UHFFFAOYSA-N 0.000 description 1
UWLHSHAHTBJTBA-UHFFFAOYSA-N 1-iodooctane Chemical compound CCCCCCCCI UWLHSHAHTBJTBA-UHFFFAOYSA-N 0.000 description 1
IUVCFHHAEHNCFT-INIZCTEOSA-N 2-[(1s)-1-[4-amino-3-(3-fluoro-4-propan-2-yloxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-6-fluoro-3-(3-fluorophenyl)chromen-4-one Chemical compound C1=C(F)C(OC(C)C)=CC=C1C(C1=C(N)N=CN=C11)=NN1[C@@H](C)C1=C(C=2C=C(F)C=CC=2)C(=O)C2=CC(F)=CC=C2O1 IUVCFHHAEHNCFT-INIZCTEOSA-N 0.000 description 1
JRQAAYVLPPGEHT-UHFFFAOYSA-N 2-bromoethylcyclohexane Chemical compound BrCCC1CCCCC1 JRQAAYVLPPGEHT-UHFFFAOYSA-N 0.000 description 1
ARXGNBZUQICZMN-UHFFFAOYSA-N 3-(2-cyclohexylethyl)-3-azabicyclo[3.1.0]hexane-2,4-dione Chemical compound O=C1C2CC2C(=O)N1CCC1CCCCC1 ARXGNBZUQICZMN-UHFFFAOYSA-N 0.000 description 1
SHZMJRRAGPZRBU-UHFFFAOYSA-N 3-(2-ethylhexyl)-3-azabicyclo[3.1.0]hexane-2,4-dione Chemical compound O=C1N(CC(CC)CCCC)C(=O)C2CC21 SHZMJRRAGPZRBU-UHFFFAOYSA-N 0.000 description 1
UCIKXDASZBDKHL-UHFFFAOYSA-N 3-(3-methylbutyl)-3-azabicyclo[3.1.0]hexane-2,4-dione Chemical compound O=C1N(CCC(C)C)C(=O)C2CC21 UCIKXDASZBDKHL-UHFFFAOYSA-N 0.000 description 1
SDHHLPLRQZJIRP-UHFFFAOYSA-N 3-(4-chlorobutyl)-3-azabicyclo[3.1.0]hexane-2,4-dione Chemical compound O=C1N(CCCCCl)C(=O)C2CC21 SDHHLPLRQZJIRP-UHFFFAOYSA-N 0.000 description 1
CVTQQNOFSSLNHV-UHFFFAOYSA-N 3-(6-hydroxyhexyl)-3-azabicyclo[3.1.0]hexane-2,4-dione Chemical compound O=C1N(CCCCCCO)C(=O)C2CC21 CVTQQNOFSSLNHV-UHFFFAOYSA-N 0.000 description 1
NZWIYPLSXWYKLH-UHFFFAOYSA-N 3-(bromomethyl)heptane Chemical compound CCCCC(CC)CBr NZWIYPLSXWYKLH-UHFFFAOYSA-N 0.000 description 1
RCPNKYBVOSFVLO-UHFFFAOYSA-N 3-[2-(cyclohexen-1-yl)ethyl]-3-azabicyclo[3.1.0]hexane-2,4-dione Chemical compound O=C1C2CC2C(=O)N1CCC1=CCCCC1 RCPNKYBVOSFVLO-UHFFFAOYSA-N 0.000 description 1
IIUJRZYHRDPLNX-UHFFFAOYSA-N 3-butyl-3-azabicyclo[3.1.0]hexane-2,4-dione Chemical compound O=C1N(CCCC)C(=O)C2CC21 IIUJRZYHRDPLNX-UHFFFAOYSA-N 0.000 description 1
LXEBMALMLHILMX-UHFFFAOYSA-N 3-decyl-3-azabicyclo[3.1.0]hexane-2,4-dione Chemical compound O=C1N(CCCCCCCCCC)C(=O)C2CC21 LXEBMALMLHILMX-UHFFFAOYSA-N 0.000 description 1
XQRJPJMBGVMAEU-UHFFFAOYSA-N 3-hept-6-enyl-3-azabicyclo[3.1.0]hexane-2,4-dione Chemical compound O=C1N(CCCCCC=C)C(=O)C2CC21 XQRJPJMBGVMAEU-UHFFFAOYSA-N 0.000 description 1
JUNIVMUYQCXIQM-UHFFFAOYSA-N 3-heptyl-3-azabicyclo[3.1.0]hexane-2,4-dione Chemical compound O=C1N(CCCCCCC)C(=O)C2CC21 JUNIVMUYQCXIQM-UHFFFAOYSA-N 0.000 description 1
XNZLEZWKXHDUFK-UHFFFAOYSA-N 3-oct-7-enyl-3-azabicyclo[3.1.0]hexane-2,4-dione Chemical compound O=C1N(CCCCCCC=C)C(=O)C2CC21 XNZLEZWKXHDUFK-UHFFFAOYSA-N 0.000 description 1
MBFXZOQQVFUIOD-UHFFFAOYSA-N 3-octan-2-yl-3-azabicyclo[3.1.0]hexane-2,4-dione Chemical compound O=C1N(C(C)CCCCCC)C(=O)C2CC21 MBFXZOQQVFUIOD-UHFFFAOYSA-N 0.000 description 1
ZRMYHUFDVLRYPN-UHFFFAOYSA-N 3-oxabicyclo[3.1.0]hexane-2,4-dione Chemical compound O=C1OC(=O)C2CC12 ZRMYHUFDVLRYPN-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
SNMOMUYLFLGQQS-UHFFFAOYSA-N 8-bromooct-1-ene Chemical compound BrCCCCCCC=C SNMOMUYLFLGQQS-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
241001539917 Actina Species 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
238000006751 Mitsunobu reaction Methods 0.000 description 1
239000007832 Na2SO4 Substances 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
150000003976 azacycloalkanes Chemical class 0.000 description 1
238000007664 blowing Methods 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
239000000969 carrier Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000010410 dusting Methods 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
UFULDTPDHIRNGS-UHFFFAOYSA-N hept-6-en-1-ol Chemical compound OCCCCCC=C UFULDTPDHIRNGS-UHFFFAOYSA-N 0.000 description 1
SXCBDZAEHILGLM-UHFFFAOYSA-N heptane-1,7-diol Chemical compound OCCCCCCCO SXCBDZAEHILGLM-UHFFFAOYSA-N 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
239000011630 iodine Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
230000000155 isotopic effect Effects 0.000 description 1
IPPVOGCPVWDIKK-UHFFFAOYSA-N n-[(3,5-dimethoxyphenyl)methyl]-n-ethylethanamine Chemical compound CCN(CC)CC1=CC(OC)=CC(OC)=C1 IPPVOGCPVWDIKK-UHFFFAOYSA-N 0.000 description 1
KPSSIOMAKSHJJG-UHFFFAOYSA-N neopentyl alcohol Chemical compound CC(C)(C)CO KPSSIOMAKSHJJG-UHFFFAOYSA-N 0.000 description 1
IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000004540 pour-on Substances 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
230000002940 repellent Effects 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
239000007921 spray Substances 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
239000003039 volatile 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
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/52—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring condensed with a ring other than six-membered
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S424/00—Drug, bio-affecting and body treating compositions
- Y10S424/10—Insect repellent

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Dentistry (AREA)
Engineering & Computer Science (AREA)
Plant Pathology (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Pest Control & Pesticides (AREA)
Agronomy & Crop Science (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Indole Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyridine Compounds (AREA)
Polysaccharides And Polysaccharide Derivatives (AREA)

OA9900043A 1996-09-26 1999-02-26 Insect-repellent formulations OA10984A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GBGB9620049.8A GB9620049D0 (en)	1996-09-26	1996-09-26	Repellent formulations

Publications (1)

Publication Number	Publication Date
OA10984A true OA10984A (en)	2001-11-05

Family

ID=10800504

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA9900043A OA10984A (en)	1996-09-26	1999-02-26	Insect-repellent formulations

Country Status (42)

Country	Link
US (1)	US6130241A (fr)
EP (1)	EP0929522B1 (fr)
JP (1)	JP3162408B2 (fr)
KR (1)	KR100324454B1 (fr)
CN (1)	CN1228768A (fr)
AP (1)	AP1014A (fr)
AR (1)	AR009812A1 (fr)
AT (1)	ATE229939T1 (fr)
AU (1)	AU716292B2 (fr)
BG (1)	BG103088A (fr)
BR (1)	BR9712127A (fr)
CA (1)	CA2266627A1 (fr)
CO (1)	CO5070676A1 (fr)
CZ (1)	CZ291905B6 (fr)
DE (1)	DE69718024D1 (fr)
DK (1)	DK0929522T3 (fr)
DZ (1)	DZ2315A1 (fr)
EA (1)	EA001880B1 (fr)
ES (1)	ES2188980T3 (fr)
GB (1)	GB9620049D0 (fr)
HN (1)	HN1997000119A (fr)
HR (1)	HRP970527B1 (fr)
HU (1)	HUP9903910A3 (fr)
ID (1)	ID21339A (fr)
IL (1)	IL127753A0 (fr)
IS (1)	IS4984A (fr)
MA (1)	MA24327A1 (fr)
MY (1)	MY131533A (fr)
NO (1)	NO991430L (fr)
NZ (1)	NZ333623A (fr)
OA (1)	OA10984A (fr)
PA (1)	PA8438001A1 (fr)
PE (1)	PE102298A1 (fr)
PL (1)	PL332574A1 (fr)
PT (1)	PT929522E (fr)
SI (1)	SI0929522T1 (fr)
SK (1)	SK38699A3 (fr)
TN (1)	TNSN97159A1 (fr)
TW (1)	TW474787B (fr)
WO (1)	WO1998013345A1 (fr)
YU (1)	YU17399A (fr)
ZA (1)	ZA978585B (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7007861B2 (en)	2000-06-08	2006-03-07	S.C. Johnson & Son, Inc.	Methods and personal protection devices for repelling insects
ATE396969T1 (de) *	2002-07-31	2008-06-15	Ranbaxy Lab Ltd	3,6-disubstituierte azabicyclo (3.1.0)hexanderivate, die sich als muscarinrezeptorantagonisten eignen
KR100978848B1 (ko) *	2008-01-17	2010-08-31	정웅선	차량 통과 저지 바 구조체
WO2016007913A1 (fr) *	2014-07-10	2016-01-14	The Arizona Board Regents On Behalf Of The University Of Arizona	Composés antimoustiques tricycliques et leurs procédés de fabrication et d'utilisation

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1770674A1 (de) *	1968-06-21	1970-02-19	Schering Ag	Pyrimidinbasen
US4183857A (en) *	1978-07-06	1980-01-15	Shell Oil Company	3-Benzyl-3-azabicyclo(3.1.0)hexane-2,4-dione
SE7713314L (sv) *	1976-12-17	1978-06-18	Rohm & Haas	Artropodrepellenter
EP0257086B1 (fr) *	1986-01-31	1993-01-20	WHITBY RESEARCH, Inc.	Peaupénétration augmentantes compositions
JPH024702A (ja) *	1988-06-22	1990-01-09	Sumitomo Chem Co Ltd	害虫忌避剤
IL102433A (en) *	1991-07-24	1996-08-04	Colgate Palmolive Co	Liquid household cleaning composition with insect repellent

1996
- 1996-09-26 GB GBGB9620049.8A patent/GB9620049D0/en active Pending
1997
- 1997-08-20 HN HN1997000119A patent/HN1997000119A/es unknown
- 1997-09-09 EP EP97942016A patent/EP0929522B1/fr not_active Expired - Lifetime
- 1997-09-09 KR KR1019997002582A patent/KR100324454B1/ko not_active Expired - Fee Related
- 1997-09-09 US US09/147,796 patent/US6130241A/en not_active Expired - Fee Related
- 1997-09-09 CA CA002266627A patent/CA2266627A1/fr not_active Abandoned
- 1997-09-09 DK DK97942016T patent/DK0929522T3/da active
- 1997-09-09 CN CN97197620A patent/CN1228768A/zh active Pending
- 1997-09-09 HU HU9903910A patent/HUP9903910A3/hu unknown
- 1997-09-09 ID IDW990121A patent/ID21339A/id unknown
- 1997-09-09 WO PCT/EP1997/004964 patent/WO1998013345A1/fr not_active Ceased
- 1997-09-09 CZ CZ1999985A patent/CZ291905B6/cs not_active IP Right Cessation
- 1997-09-09 SI SI9730446T patent/SI0929522T1/xx unknown
- 1997-09-09 JP JP51520798A patent/JP3162408B2/ja not_active Expired - Fee Related
- 1997-09-09 SK SK386-99A patent/SK38699A3/sk unknown
- 1997-09-09 AU AU43844/97A patent/AU716292B2/en not_active Ceased
- 1997-09-09 YU YU17399A patent/YU17399A/sh unknown
- 1997-09-09 DE DE69718024T patent/DE69718024D1/de not_active Expired - Fee Related
- 1997-09-09 EA EA199900230A patent/EA001880B1/ru not_active IP Right Cessation
- 1997-09-09 AT AT97942016T patent/ATE229939T1/de not_active IP Right Cessation
- 1997-09-09 NZ NZ333623A patent/NZ333623A/xx unknown
- 1997-09-09 PT PT97942016T patent/PT929522E/pt unknown
- 1997-09-09 IL IL12775397A patent/IL127753A0/xx unknown
- 1997-09-09 PL PL97332574A patent/PL332574A1/xx unknown
- 1997-09-09 ES ES97942016T patent/ES2188980T3/es not_active Expired - Lifetime
- 1997-09-09 BR BR9712127-4A patent/BR9712127A/pt not_active IP Right Cessation
- 1997-09-12 PA PA19978438001A patent/PA8438001A1/es unknown
- 1997-09-19 PE PE1997000837A patent/PE102298A1/es not_active Application Discontinuation
- 1997-09-24 AP APAP/P/1997/001108A patent/AP1014A/en active
- 1997-09-24 DZ DZ970165A patent/DZ2315A1/fr active
- 1997-09-24 AR ARP970104380A patent/AR009812A1/es not_active Application Discontinuation
- 1997-09-24 TN TNTNSN97159A patent/TNSN97159A1/fr unknown
- 1997-09-24 MY MYPI97004438A patent/MY131533A/en unknown
- 1997-09-24 TW TW086113912A patent/TW474787B/zh not_active IP Right Cessation
- 1997-09-24 MA MA24808A patent/MA24327A1/fr unknown
- 1997-09-24 CO CO97055767A patent/CO5070676A1/es unknown
- 1997-09-25 HR HR970527A patent/HRP970527B1/xx not_active IP Right Cessation
- 1997-09-25 ZA ZA978585A patent/ZA978585B/xx unknown
1999
- 1999-01-15 BG BG103088A patent/BG103088A/bg unknown
- 1999-02-26 IS IS4984A patent/IS4984A/is unknown
- 1999-02-26 OA OA9900043A patent/OA10984A/en unknown
- 1999-03-24 NO NO991430A patent/NO991430L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
MY131533A (en)	2007-08-30
ES2188980T3 (es)	2003-07-01
PT929522E (pt)	2003-03-31
IS4984A (is)	1999-02-26
US6130241A (en)	2000-10-10
AP9701108A0 (en)	1997-10-31
PE102298A1 (es)	1999-01-08
DK0929522T3 (da)	2003-04-14
EA199900230A1 (ru)	1999-10-28
HUP9903910A3 (en)	2001-02-28
YU17399A (sh)	2002-11-15
ZA978585B (en)	1999-03-25
ID21339A (id)	1999-05-27
TW474787B (en)	2002-02-01
SI0929522T1 (en)	2003-04-30
AR009812A1 (es)	2000-05-03
CN1228768A (zh)	1999-09-15
CZ98599A3 (cs)	2000-02-16
GB9620049D0 (en)	1996-11-13
HN1997000119A (es)	1997-12-26
AU716292B2 (en)	2000-02-24
PL332574A1 (en)	1999-09-27
CO5070676A1 (es)	2001-08-28
BG103088A (bg)	1999-11-30
CA2266627A1 (fr)	1998-04-02
CZ291905B6 (cs)	2003-06-18
DZ2315A1 (fr)	2002-12-28
NZ333623A (en)	2000-04-28
HUP9903910A2 (hu)	2000-03-28
BR9712127A (pt)	1999-08-31
JP3162408B2 (ja)	2001-04-25
KR20000048640A (ko)	2000-07-25
SK38699A3 (en)	2000-05-16
AP1014A (en)	2001-09-28
EA001880B1 (ru)	2001-10-22
PA8438001A1 (es)	2000-05-24
EP0929522A1 (fr)	1999-07-21
IL127753A0 (en)	1999-10-28
JP2000502362A (ja)	2000-02-29
AU4384497A (en)	1998-04-17
KR100324454B1 (ko)	2002-02-27
EP0929522B1 (fr)	2002-12-18
HRP970527B1 (en)	2002-06-30
WO1998013345A1 (fr)	1998-04-02
HRP970527A2 (en)	1998-08-31
TNSN97159A1 (fr)	2005-03-15
MA24327A1 (fr)	1998-04-01
NO991430D0 (no)	1999-03-24
NO991430L (no)	1999-03-24
DE69718024D1 (de)	2003-01-30
ATE229939T1 (de)	2003-01-15

Publication	Publication Date	Title
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US3835176A (en)	1974-09-10	Alpha-cyanobenzyl cyclopropanecarboxylates
JPH04211082A (ja)	1992-08-03	多環式３−アリール−ピロリジン−２，４−ジオン誘導体
JP2605099B2 (ja)	1997-04-30	昆虫及びダニの忌避剤
HK61185A (en)	1985-08-23	New cyclopropanecarboxylates, their production and insecticide containing them as an active ingredient
OA10984A (en)	2001-11-05	Insect-repellent formulations
US3795696A (en)	1974-03-05	Alkynylbenzyl cyclopropane-carboxylates
US3669989A (en)	1972-06-13	Cyclopropanecarboxylic acid esters
US10435344B2 (en)	2019-10-08	Reaction sequence for the synthesis of nootkatone, dihydronootkatone, and tetrahydronootkatone
US4327094A (en)	1982-04-27	Insecticidal and acaricidal 3,5-dioxo-2,3,4,5-triazine compounds
EP0037851A2 (fr)	1981-10-21	Carboxylates, procédé pour leur préparation, composition insecticide et/ou acaricide et utilisation des composés comme insecticides et/ou acaricides
US4480118A (en)	1984-10-30	Carboxylic acid ester and an insecticidal and/or acaricidal composition containing the same
RU2088571C1 (ru)	1997-08-27	Производные малоновой кислоты
DE2138334C3 (de)	1976-06-24	Furfuryl- oder Thenylcyclopropancarbonsäureester, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide
Whittaker	1995	AN INVESTIGATION OF REACTIONS DIRECTED TOWARDS"': fHE SYNTHESIS OF 2-METHYL-2-(METHYLTHIO) PROPANAL OXIME
JPS6160651A (ja)	1986-03-28	フエニルピリジルエチレン誘導体およびそれを有効成分とする除草剤
JPH0122255B2 (fr)	1989-04-25
JPH0122256B2 (fr)	1989-04-25
JPH1072414A (ja)	1998-03-17	置換ベンゼン誘導体
JPH0253758A (ja)	1990-02-22	アミド化合物
FR2583045A1 (fr)	1986-12-12	Procede de preparation de derives de pyrethroides