AP969A - Benzazoles: benxoxazole, benzthiazole and benzimidazole derivatives. - Google Patents

Benzazoles: benxoxazole, benzthiazole and benzimidazole derivatives. Download PDF

Info

Publication number: AP969A
Authority: AP; ARIPO
Prior art keywords: alkyl; hydrogen; compounds; phenyl; methyl
Prior art date: 1998-07-30

Application number

APAP/P/1999/001616A

Other languages

English (en)

Other versions

AP9901616A0 (en

Inventor

Christopher John Williams

John Williams

Brian Leslie Pilkington

Alan John Whittle

Christopher John Urch

Patrick Jelf Crowley

Original Assignee

Zeneca Ltd

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.)

1998-07-30

Filing date

1999-07-29

Publication date

2001-05-29

1999-07-29 Application filed by Zeneca Ltd filed Critical Zeneca Ltd

1999-09-30 Publication of AP9901616A0 publication Critical patent/AP9901616A0/xx

2001-05-29 Application granted granted Critical

2001-05-29 Publication of AP969A publication Critical patent/AP969A/en

Links

IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 title description 4
229940058303 antinematodal benzimidazole derivative Drugs 0.000 title description 2
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical class C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title 1
125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 title 1
150000001875 compounds Chemical class 0.000 abstract description 212
125000000217 alkyl group Chemical group 0.000 abstract description 156
229910052739 hydrogen Inorganic materials 0.000 abstract description 144
239000001257 hydrogen Substances 0.000 abstract description 143
229910052760 oxygen Inorganic materials 0.000 abstract description 110
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 101
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 61
125000004093 cyano group Chemical group *C#N 0.000 abstract description 45
125000001188 haloalkyl group Chemical group 0.000 abstract description 40
125000003545 alkoxy group Chemical group 0.000 abstract description 39
150000002431 hydrogen Chemical group 0.000 abstract description 37
229910052736 halogen Inorganic materials 0.000 abstract description 29
150000002367 halogens Chemical class 0.000 abstract description 29
125000004453 alkoxycarbonyl group Chemical group 0.000 abstract description 24
125000004448 alkyl carbonyl group Chemical group 0.000 abstract description 24
125000000753 cycloalkyl group Chemical group 0.000 abstract description 22
125000003342 alkenyl group Chemical group 0.000 abstract description 21
125000000304 alkynyl group Chemical group 0.000 abstract description 18
125000001072 heteroaryl group Chemical group 0.000 abstract description 18
125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract description 15
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract description 14
125000004457 alkyl amino carbonyl group Chemical group 0.000 abstract description 12
125000004966 cyanoalkyl group Chemical group 0.000 abstract description 12
125000004438 haloalkoxy group Chemical group 0.000 abstract description 12
125000004414 alkyl thio group Chemical group 0.000 abstract description 11
125000000623 heterocyclic group Chemical group 0.000 abstract description 10
125000000262 haloalkenyl group Chemical group 0.000 abstract description 8
125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 abstract description 8
125000006678 phenoxycarbonyl group Chemical group 0.000 abstract description 8
125000000392 cycloalkenyl group Chemical group 0.000 abstract description 7
125000004995 haloalkylthio group Chemical group 0.000 abstract description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 5
229910052717 sulfur Inorganic materials 0.000 abstract description 5
125000005347 halocycloalkyl group Chemical group 0.000 abstract description 4
229920006395 saturated elastomer Polymers 0.000 abstract description 4
125000004390 alkyl sulfonyl group Chemical group 0.000 abstract description 3
125000004440 haloalkylsulfinyl group Chemical group 0.000 abstract description 3
125000002837 carbocyclic group Chemical group 0.000 abstract description 2
125000004181 carboxyalkyl group Chemical group 0.000 abstract description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 128
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 108
239000001301 oxygen Substances 0.000 description 108
-1 fro-propyl Chemical group 0.000 description 76
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 60
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 35
239000005864 Sulphur Chemical group 0.000 description 34
YMEHWISYYMKMFO-WOMRJYOTSA-N methyl N-[(12E,15S)-15-[(4S)-4-(3-chlorophenyl)-2-oxopiperidin-1-yl]-9-oxo-8,17,19-triazatricyclo[14.2.1.02,7]nonadeca-1(18),2(7),3,5,12,16-hexaen-5-yl]carbamate Chemical compound COC(=O)Nc1ccc2-c3cnc([nH]3)[C@H](C\C=C\CCC(=O)Nc2c1)N1CC[C@@H](CC1=O)c1cccc(Cl)c1 YMEHWISYYMKMFO-WOMRJYOTSA-N 0.000 description 33
125000001309 chloro group Chemical group Cl* 0.000 description 30
125000001246 bromo group Chemical group Br* 0.000 description 27
125000001153 fluoro group Chemical group F* 0.000 description 27
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 12
125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 8
125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 6
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
239000000460 chlorine Substances 0.000 description 5
125000005842 heteroatom Chemical group 0.000 description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
125000001424 substituent group Chemical group 0.000 description 5
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 5
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 4
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
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 4
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 4
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
229910052757 nitrogen Chemical group 0.000 description 4
125000004076 pyridyl group Chemical group 0.000 description 4
JPRPJUMQRZTTED-UHFFFAOYSA-N 1,3-dioxolanyl Chemical group [CH]1OCCO1 JPRPJUMQRZTTED-UHFFFAOYSA-N 0.000 description 3
101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 description 3
125000004849 alkoxymethyl group Chemical group 0.000 description 3
125000004429 atom Chemical group 0.000 description 3
239000011737 fluorine Substances 0.000 description 3
229910052731 fluorine Inorganic materials 0.000 description 3
125000002541 furyl group Chemical group 0.000 description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
125000002757 morpholinyl group Chemical group 0.000 description 3
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 3
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 3
125000001544 thienyl group Chemical group 0.000 description 3
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 2
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
101150065749 Churc1 gene Proteins 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
208000031888 Mycoses Diseases 0.000 description 2
102100038239 Protein Churchill Human genes 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
125000005079 alkoxycarbonylmethyl group Chemical group 0.000 description 2
125000004644 alkyl sulfinyl group Chemical group 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 2
125000004441 haloalkylsulfonyl group Chemical group 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
150000003854 isothiazoles Chemical class 0.000 description 2
125000000842 isoxazolyl group Chemical group 0.000 description 2
125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 2
239000000203 mixture Substances 0.000 description 2
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 2
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
125000003226 pyrazolyl group Chemical group 0.000 description 2
125000000714 pyrimidinyl group Chemical group 0.000 description 2
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 2
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 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
125000006656 (C2-C4) alkenyl group Chemical group 0.000 description 1
BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
LJXPWUAAAAXJBX-UHFFFAOYSA-N 2-methylallyl radical Chemical compound [CH2]C(C)=C LJXPWUAAAAXJBX-UHFFFAOYSA-N 0.000 description 1
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
125000006519 CCH3 Chemical group 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
241000238631 Hexapoda Species 0.000 description 1
241000237852 Mollusca Species 0.000 description 1
241000244206 Nematoda Species 0.000 description 1
ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
241000607479 Yersinia pestis Species 0.000 description 1
230000000895 acaricidal effect Effects 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
125000003282 alkyl amino group Chemical group 0.000 description 1
RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
AOJDZKCUAATBGE-UHFFFAOYSA-N bromomethane Chemical compound Br[CH2] AOJDZKCUAATBGE-UHFFFAOYSA-N 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 description 1
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
125000004663 dialkyl amino group Chemical group 0.000 description 1
230000000855 fungicidal effect Effects 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
230000000749 insecticidal effect Effects 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 description 1
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
125000004372 methylthioethyl group Chemical group [H]C([H])([H])SC([H])([H])C([H])([H])* 0.000 description 1
230000002013 molluscicidal effect Effects 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-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
230000001069 nematicidal effect Effects 0.000 description 1
125000005244 neohexyl group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000006574 non-aromatic ring group Chemical group 0.000 description 1
125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
OSFBJERFMQCEQY-UHFFFAOYSA-N propylidene Chemical compound [CH]CC OSFBJERFMQCEQY-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
239000011593 sulfur Chemical group 0.000 description 1
125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2

Landscapes

Life Sciences & Earth Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Environmental Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Plant Pathology (AREA)
Pest Control & Pesticides (AREA)
Agronomy & Crop Science (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

APAP/P/1999/001616A 1998-07-30 1999-07-29 Benzazoles: benxoxazole, benzthiazole and benzimidazole derivatives. AP969A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GBGB9816654.9A GB9816654D0 (en)	1998-07-30	1998-07-30	Chemical compounds

Publications (2)

Publication Number	Publication Date
AP9901616A0 AP9901616A0 (en)	1999-09-30
AP969A true AP969A (en)	2001-05-29

Family

ID=10836466

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
APAP/P/1999/001616A AP969A (en)	1998-07-30	1999-07-29	Benzazoles: benxoxazole, benzthiazole and benzimidazole derivatives.

Country Status (30)

Country	Link
US (1)	US6544989B2 (es)
EP (1)	EP1100798B1 (es)
JP (1)	JP4545933B2 (es)
KR (1)	KR100558630B1 (es)
CN (1)	CN1196699C (es)
AP (1)	AP969A (es)
AR (1)	AR019486A1 (es)
AT (1)	ATE224390T1 (es)
AU (1)	AU755291B2 (es)
BR (1)	BR9912616A (es)
CA (1)	CA2338048C (es)
CO (1)	CO5190721A1 (es)
DE (1)	DE69903044T2 (es)
DK (1)	DK1100798T3 (es)
EG (1)	EG22178A (es)
ES (1)	ES2184482T3 (es)
GB (1)	GB9816654D0 (es)
GT (1)	GT199900119A (es)
HK (1)	HK1040714A1 (es)
HN (1)	HN1999000127A (es)
HU (1)	HUP0103695A3 (es)
IL (2)	IL141109A0 (es)
MY (1)	MY133385A (es)
NZ (1)	NZ509431A (es)
PE (1)	PE20001005A1 (es)
PT (1)	PT1100798E (es)
SV (1)	SV1999000119A (es)
TW (1)	TW522151B (es)
WO (1)	WO2000006566A1 (es)
ZA (1)	ZA200100780B (es)

Families Citing this family (40)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2001046165A2 (en) *	1999-12-16	2001-06-28	Novartis Ag	N-heteroaryl-amides and their use as parasiticides
GB0002031D0 (en) *	2000-01-28	2000-03-22	Zeneca Ltd	Chemical compounds
PE20010830A1 (es) *	2000-01-28	2001-09-06	Syngenta Ltd	Derivados de azol insecticidas o fungicidas y composiciones que los comprenden
GB0002036D0 (en) *	2000-01-28	2000-03-22	Zeneca Ltd	Chemical compounds
GB0002041D0 (en) *	2000-01-28	2000-03-22	Zeneca Ltd	Chemical compounds
GB0002040D0 (en) *	2000-01-28	2000-03-22	Zeneca Ltd	Chemical compounds
GB0002033D0 (en) *	2000-01-28	2000-03-22	Zeneca Ltd	Chemical compounds
GB0002029D0 (en) *	2000-01-28	2000-03-22	Zeneca Ltd	Chemical compounds
GB0012806D0 (en) *	2000-05-25	2000-07-19	Zeneca Ltd	Chemical compounds
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Also Published As

Publication number	Publication date
IL141109A (en)	2007-07-24
AP9901616A0 (en)	1999-09-30
IL141109A0 (en)	2002-02-10
US6544989B2 (en)	2003-04-08
EP1100798A1 (en)	2001-05-23
HUP0103695A3 (en)	2002-04-29
GB9816654D0 (en)	1998-09-30
BR9912616A (pt)	2002-02-13
PE20001005A1 (es)	2000-10-09
KR100558630B1 (ko)	2006-03-13
MY133385A (en)	2007-11-30
EG22178A (en)	2002-10-31
JP4545933B2 (ja)	2010-09-15
PT1100798E (pt)	2003-02-28
WO2000006566A1 (en)	2000-02-10
EP1100798B1 (en)	2002-09-18
NZ509431A (en)	2003-08-29
CN1320124A (zh)	2001-10-31
TW522151B (en)	2003-03-01
DE69903044T2 (de)	2003-06-12
SV1999000119A (es)	2000-05-02
CN1196699C (zh)	2005-04-13
AU755291B2 (en)	2002-12-12
DE69903044D1 (de)	2002-10-24
ES2184482T3 (es)	2003-04-01
US20020049142A1 (en)	2002-04-25
CA2338048A1 (en)	2000-02-10
JP2002521480A (ja)	2002-07-16
DK1100798T3 (da)	2002-10-14
HN1999000127A (es)	1999-11-11
HUP0103695A2 (hu)	2002-01-28
GT199900119A (es)	2000-11-16
ATE224390T1 (de)	2002-10-15
AR019486A1 (es)	2002-02-20
AU5055099A (en)	2000-02-21
ZA200100780B (en)	2002-06-26
CO5190721A1 (es)	2002-08-29
HK1040714A1 (zh)	2002-06-21
KR20010085317A (ko)	2001-09-07
CA2338048C (en)	2010-01-12

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CN110894190B (zh)	2020-09-11	三氮唑化合物及其在农业中的应用
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JP2009511447A (ja)	2009-03-19	新規ｎ−アルキル−ヘテロシクリルカルボキサミド誘導体
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