BG103088A - Репелентни състави срещу насекоми - Google Patents

Репелентни състави срещу насекоми Download PDF

Info

Publication number: BG103088A
Authority: BG; Bulgaria
Prior art keywords: compound; formula; hexane; straight; repellent composition
Prior art date: 1996-09-26

Application number

BG103088A

Other languages

Bulgarian (bg)

English (en)

Inventor

Darren SCHULZ

Original Assignee

Pfizer Inc.

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

1999-01-15

Publication date

1999-11-30

1999-01-15 Application filed by Pfizer Inc. filed Critical Pfizer Inc.

1999-11-30 Publication of BG103088A publication Critical patent/BG103088A/bg

Links

239000000203 mixture Substances 0.000 title claims abstract description 43
230000002940 repellent Effects 0.000 title claims abstract description 16
239000005871 repellent Substances 0.000 title claims abstract description 16
241000238631 Hexapoda Species 0.000 title claims abstract description 11
150000001875 compounds Chemical class 0.000 claims abstract description 57
239000002904 solvent Substances 0.000 claims abstract description 12
229910052736 halogen Inorganic materials 0.000 claims abstract description 6
125000003342 alkenyl group Chemical group 0.000 claims abstract description 5
125000000217 alkyl group Chemical group 0.000 claims abstract description 5
150000002367 halogens Chemical class 0.000 claims abstract description 5
125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 3
125000000304 alkynyl group Chemical group 0.000 claims abstract 2
-1 6-hepten-1-yl Chemical group 0.000 claims description 43
238000000034 method Methods 0.000 claims description 15
241000238876 Acari Species 0.000 claims description 12
241000255925 Diptera Species 0.000 claims description 9
241000124008 Mammalia 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
241001465754 Metazoa Species 0.000 claims description 5
FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 claims description 5
FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 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
229910052801 chlorine Inorganic materials 0.000 claims description 4
239000000460 chlorine Substances 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
125000004043 oxo group Chemical group O=* 0.000 claims description 4
101100037762 Caenorhabditis elegans rnh-2 gene Proteins 0.000 claims description 3
239000006210 lotion Substances 0.000 claims description 3
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
230000001846 repelling effect Effects 0.000 claims description 3
239000002671 adjuvant Substances 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 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
229910052740 iodine Inorganic materials 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 33
NDOGLIPWGGRQCO-UHFFFAOYSA-N hexane-2,4-dione Chemical compound CCC(=O)CC(C)=O NDOGLIPWGGRQCO-UHFFFAOYSA-N 0.000 description 31
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 28
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
239000011541 reaction mixture Substances 0.000 description 22
238000005481 NMR spectroscopy Methods 0.000 description 19
239000004698 Polyethylene Substances 0.000 description 18
229920000573 polyethylene Polymers 0.000 description 18
239000003921 oil Substances 0.000 description 14
239000007921 spray Substances 0.000 description 13
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
239000012230 colorless oil Substances 0.000 description 12
239000012299 nitrogen atmosphere Substances 0.000 description 12
238000003756 stirring Methods 0.000 description 12
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
239000000284 extract Substances 0.000 description 10
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
238000012360 testing method Methods 0.000 description 8
238000009835 boiling Methods 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
238000004587 chromatography analysis Methods 0.000 description 6
239000012312 sodium hydride Substances 0.000 description 6
229910000104 sodium hydride Inorganic materials 0.000 description 6
238000000023 Kugelrohr distillation Methods 0.000 description 5
230000008569 process Effects 0.000 description 5
239000000377 silicon dioxide Substances 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
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
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 4
230000015572 biosynthetic process Effects 0.000 description 4
239000000077 insect repellent Substances 0.000 description 4
229910052943 magnesium sulfate Inorganic materials 0.000 description 4
235000019341 magnesium sulphate Nutrition 0.000 description 4
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 4
239000002674 ointment Substances 0.000 description 4
238000010898 silica gel chromatography Methods 0.000 description 4
239000011734 sodium Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
229960005323 phenoxyethanol Drugs 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
150000003976 azacycloalkanes Chemical class 0.000 description 2
239000001569 carbon dioxide Substances 0.000 description 2
229910002092 carbon dioxide Inorganic materials 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
230000001804 emulsifying effect Effects 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
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 2
238000000338 in vitro Methods 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
230000005012 migration Effects 0.000 description 2
238000013508 migration Methods 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 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
239000000047 product Substances 0.000 description 2
239000008213 purified water Substances 0.000 description 2
239000000344 soap Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
238000006467 substitution reaction Methods 0.000 description 2
239000000725 suspension Substances 0.000 description 2
238000005292 vacuum distillation Methods 0.000 description 2
MFDSUEYHCWXFSD-UHFFFAOYSA-N 1-chloro-4-iodooctane Chemical compound CCCCC(I)CCCCl MFDSUEYHCWXFSD-UHFFFAOYSA-N 0.000 description 1
BUZZUHJODKQYTF-UHFFFAOYSA-N 1-iodo-3-methylbutane Chemical compound CC(C)CCI BUZZUHJODKQYTF-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
IUDMXOOVKMKODN-UHFFFAOYSA-N 2-(cyclohexen-1-yl)ethanamine Chemical compound NCCC1=CCCCC1 IUDMXOOVKMKODN-UHFFFAOYSA-N 0.000 description 1
FTJHYGJLHCGQHQ-UHFFFAOYSA-N 2-bromooctane Chemical compound CCCCCCC(C)Br FTJHYGJLHCGQHQ-UHFFFAOYSA-N 0.000 description 1
NZWIYPLSXWYKLH-UHFFFAOYSA-N 3-(bromomethyl)heptane Chemical compound CCCCC(CC)CBr NZWIYPLSXWYKLH-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
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
241000282412 Homo Species 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
239000006096 absorbing agent Substances 0.000 description 1
230000009471 action Effects 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
230000008901 benefit Effects 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
239000000470 constituent Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
KXZHGRCUIXYVFJ-UHFFFAOYSA-N diethylamino thiohypofluorite Chemical compound CCN(CC)SF KXZHGRCUIXYVFJ-UHFFFAOYSA-N 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000004744 fabric Substances 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000000499 gel Substances 0.000 description 1
238000010438 heat treatment Methods 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
TXGJTWACJNYNOJ-UHFFFAOYSA-N hexane-2,4-diol Chemical compound CCC(O)CC(C)O TXGJTWACJNYNOJ-UHFFFAOYSA-N 0.000 description 1
125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
230000003993 interaction Effects 0.000 description 1
239000011630 iodine Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000000155 melt Substances 0.000 description 1
238000002156 mixing Methods 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
239000000546 pharmaceutical excipient 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
230000003389 potentiating effect Effects 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
239000002453 shampoo Substances 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 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
238000010183 spectrum analysis Methods 0.000 description 1
230000007480 spreading Effects 0.000 description 1
230000000638 stimulation Effects 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

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)
Polysaccharides And Polysaccharide Derivatives (AREA)
Pyridine Compounds (AREA)

BG103088A 1996-09-26 1999-01-15 Репелентни състави срещу насекоми BG103088A (bg)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GBGB9620049.8A GB9620049D0 (en)	1996-09-26	1996-09-26	Repellent formulations
PCT/EP1997/004964 WO1998013345A1 (en)	1996-09-26	1997-09-09	Insect-repellent formulations

Publications (1)

Publication Number	Publication Date
BG103088A true BG103088A (bg)	1999-11-30

Family

ID=10800504

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BG103088A BG103088A (bg)	1996-09-26	1999-01-15	Репелентни състави срещу насекоми

Country Status (42)

Country	Link
US (1)	US6130241A (is)
EP (1)	EP0929522B1 (is)
JP (1)	JP3162408B2 (is)
KR (1)	KR100324454B1 (is)
CN (1)	CN1228768A (is)
AP (1)	AP1014A (is)
AR (1)	AR009812A1 (is)
AT (1)	ATE229939T1 (is)
AU (1)	AU716292B2 (is)
BG (1)	BG103088A (is)
BR (1)	BR9712127A (is)
CA (1)	CA2266627A1 (is)
CO (1)	CO5070676A1 (is)
CZ (1)	CZ291905B6 (is)
DE (1)	DE69718024D1 (is)
DK (1)	DK0929522T3 (is)
DZ (1)	DZ2315A1 (is)
EA (1)	EA001880B1 (is)
ES (1)	ES2188980T3 (is)
GB (1)	GB9620049D0 (is)
HN (1)	HN1997000119A (is)
HR (1)	HRP970527B1 (is)
HU (1)	HUP9903910A3 (is)
ID (1)	ID21339A (is)
IL (1)	IL127753A0 (is)
IS (1)	IS4984A (is)
MA (1)	MA24327A1 (is)
MY (1)	MY131533A (is)
NO (1)	NO991430D0 (is)
NZ (1)	NZ333623A (is)
OA (1)	OA10984A (is)
PA (1)	PA8438001A1 (is)
PE (1)	PE102298A1 (is)
PL (1)	PL332574A1 (is)
PT (1)	PT929522E (is)
SI (1)	SI0929522T1 (is)
SK (1)	SK38699A3 (is)
TN (1)	TNSN97159A1 (is)
TW (1)	TW474787B (is)
WO (1)	WO1998013345A1 (is)
YU (1)	YU17399A (is)
ZA (1)	ZA978585B (is)

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
HK1079787A1 (zh) *	2002-07-31	2006-04-13	Ranbaxy Laboratories Limited	用作毒蕈碱受体拮抗剂的3，6-二取代的氮杂双环[3．1．0]己烷衍生物
KR100978848B1 (ko) *	2008-01-17	2010-08-31	정웅선	차량 통과 저지 바 구조체
US10370385B2 (en)	2014-07-10	2019-08-06	Arizona Board Of Regents On Behalf Of The University Of Arizona	Tricyclic mosquitocides and methods of making and using thereof

Family Cites Families (6)

* 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
US4886545A (en) *	1986-01-31	1989-12-12	Nelson Research & Development Company	Compositions comprising 1-substituted azacycloalkanes and their uses
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 HU HU9903910A patent/HUP9903910A3/hu unknown
- 1997-09-09 DE DE69718024T patent/DE69718024D1/de not_active Expired - Fee Related
- 1997-09-09 EP EP97942016A patent/EP0929522B1/en not_active Expired - Lifetime
- 1997-09-09 CA CA002266627A patent/CA2266627A1/en not_active Abandoned
- 1997-09-09 WO PCT/EP1997/004964 patent/WO1998013345A1/en not_active Ceased
- 1997-09-09 PL PL97332574A patent/PL332574A1/xx unknown
- 1997-09-09 DK DK97942016T patent/DK0929522T3/da active
- 1997-09-09 SK SK386-99A patent/SK38699A3/sk unknown
- 1997-09-09 CZ CZ1999985A patent/CZ291905B6/cs not_active IP Right Cessation
- 1997-09-09 YU YU17399A patent/YU17399A/sh unknown
- 1997-09-09 KR KR1019997002582A patent/KR100324454B1/ko not_active Expired - Fee Related
- 1997-09-09 AU AU43844/97A patent/AU716292B2/en not_active Ceased
- 1997-09-09 IL IL12775397A patent/IL127753A0/xx unknown
- 1997-09-09 PT PT97942016T patent/PT929522E/pt unknown
- 1997-09-09 NZ NZ333623A patent/NZ333623A/xx unknown
- 1997-09-09 AT AT97942016T patent/ATE229939T1/de not_active IP Right Cessation
- 1997-09-09 BR BR9712127-4A patent/BR9712127A/pt not_active IP Right Cessation
- 1997-09-09 ID IDW990121A patent/ID21339A/id unknown
- 1997-09-09 US US09/147,796 patent/US6130241A/en not_active Expired - Fee Related
- 1997-09-09 JP JP51520798A patent/JP3162408B2/ja not_active Expired - Fee Related
- 1997-09-09 EA EA199900230A patent/EA001880B1/ru not_active IP Right Cessation
- 1997-09-09 ES ES97942016T patent/ES2188980T3/es not_active Expired - Lifetime
- 1997-09-09 CN CN97197620A patent/CN1228768A/zh active Pending
- 1997-09-09 SI SI9730446T patent/SI0929522T1/xx unknown
- 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 AR ARP970104380A patent/AR009812A1/es not_active Application Discontinuation
- 1997-09-24 MY MYPI97004438A patent/MY131533A/en unknown
- 1997-09-24 MA MA24808A patent/MA24327A1/fr unknown
- 1997-09-24 TW TW086113912A patent/TW474787B/zh not_active IP Right Cessation
- 1997-09-24 TN TNTNSN97159A patent/TNSN97159A1/fr unknown
- 1997-09-24 DZ DZ970165A patent/DZ2315A1/xx active
- 1997-09-24 CO CO97055767A patent/CO5070676A1/es unknown
- 1997-09-25 ZA ZA978585A patent/ZA978585B/xx unknown
- 1997-09-25 HR HR970527A patent/HRP970527B1/xx not_active IP Right Cessation
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/NO991430D0/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
DZ2315A1 (fr)	2002-12-28
OA10984A (en)	2001-11-05
JP2000502362A (ja)	2000-02-29
SK38699A3 (en)	2000-05-16
MY131533A (en)	2007-08-30
AU4384497A (en)	1998-04-17
NZ333623A (en)	2000-04-28
PL332574A1 (en)	1999-09-27
CZ98599A3 (cs)	2000-02-16
GB9620049D0 (en)	1996-11-13
MA24327A1 (fr)	1998-04-01
KR100324454B1 (ko)	2002-02-27
PE102298A1 (es)	1999-01-08
IL127753A0 (en)	1999-10-28
PT929522E (pt)	2003-03-31
ATE229939T1 (de)	2003-01-15
JP3162408B2 (ja)	2001-04-25
AP1014A (en)	2001-09-28
TW474787B (en)	2002-02-01
AP9701108A0 (en)	1997-10-31
DK0929522T3 (da)	2003-04-14
DE69718024D1 (de)	2003-01-30
ZA978585B (en)	1999-03-25
AU716292B2 (en)	2000-02-24
EA001880B1 (ru)	2001-10-22
PA8438001A1 (es)	2000-05-24
WO1998013345A1 (en)	1998-04-02
NO991430L (no)	1999-03-24
HRP970527B1 (en)	2002-06-30
EP0929522B1 (en)	2002-12-18
CN1228768A (zh)	1999-09-15
US6130241A (en)	2000-10-10
NO991430D0 (no)	1999-03-24
ID21339A (id)	1999-05-27
EP0929522A1 (en)	1999-07-21
HUP9903910A3 (en)	2001-02-28
EA199900230A1 (ru)	1999-10-28
TNSN97159A1 (fr)	2005-03-15
IS4984A (is)	1999-02-26
HRP970527A2 (en)	1998-08-31
HN1997000119A (es)	1997-12-26
KR20000048640A (ko)	2000-07-25
YU17399A (sh)	2002-11-15
SI0929522T1 (en)	2003-04-30
CA2266627A1 (en)	1998-04-02
HUP9903910A2 (hu)	2000-03-28
ES2188980T3 (es)	2003-07-01
CO5070676A1 (es)	2001-08-28
CZ291905B6 (cs)	2003-06-18
AR009812A1 (es)	2000-05-03
BR9712127A (pt)	1999-08-31

Publication	Publication Date	Title
US3973036A (en)	1976-08-03	Cyclopropanecarboxylic acid esters
US4212879A (en)	1980-07-15	Benzyl pyrrolyl methyl carboxylate insecticides and acaricides
JP2605099B2 (ja)	1997-04-30	昆虫及びダニの忌避剤
JPH0729989B2 (ja)	1995-04-05	ピレトリン酸と関連した新規なシクロプロパンカルボン酸エステル、その製造法及び害虫駆除への使用
JPH02233644A (ja)	1990-09-17	新規の２，２―ジメチル―３―（２―モノハロエテニル）シクロプロパンカルボン酸誘導体、それらの製造方法及び害虫駆除剤としてのそれらの使用
BG103088A (bg)	1999-11-30	Репелентни състави срещу насекоми
US7435851B2 (en)	2008-10-14	Puleganic amides
CN1953971A (zh)	2007-04-25	二氢假荆芥内酯衍生物及其制备方法
US5892133A (en)	1999-04-06	Repellent agent against harmful insects and perfume composition containing the same
CA1058623A (en)	1979-07-17	Insecticides
US3669989A (en)	1972-06-13	Cyclopropanecarboxylic acid esters
DE69129213T2 (de)	1998-07-30	Mittel zur Insektenabwehr
US4522749A (en)	1985-06-11	Process for augmenting or enhancing the aroma of a fragrance by adding a vinylcyclopropane compound
JPS58121246A (ja)	1983-07-19	置換ベンジルエステル及びこれを有効成分とする殺虫剤
JPS6253497B2 (is)	1987-11-10
JPH0267258A (ja)	1990-03-07	アミド化合物
JPS58118533A (ja)	1983-07-14	３−フエノキシ−４−フルオロベンジル２−（４−エトキシフエニル）−２−メチルプロピルエ−テル、その製造法および殺虫、殺ダニ剤
JPH0122255B2 (is)	1989-04-25
JPS60100541A (ja)	1985-06-04	炭化水素系化合物、その製造法およびそれを有効成分とする殺虫、殺ダニ剤
JPH0122253B2 (is)	1989-04-25
JPH0122256B2 (is)	1989-04-25
JPS6253498B2 (is)	1987-11-10