AP969A - Benzazoles: benxoxazole, benzthiazole and benzimidazole derivatives. - Google Patents
Benzazoles: benxoxazole, benzthiazole and benzimidazole derivatives. Download PDFInfo
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- AP969A AP969A APAP/P/1999/001616A AP9901616A AP969A AP 969 A AP969 A AP 969A AP 9901616 A AP9901616 A AP 9901616A AP 969 A AP969 A AP 969A
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- 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
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- 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
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Abstract
A compound of formula fir is hydrogen, halogen, CM alkyl, CM alkoxy. CM haloalkoxy. CM alkylthio, CM haloalkylthio. Cualkylsulfuiyl, CM haloalkylsulfinyl, CM alkylsulfonyl, CM haloaikylsulfonyl, CM haloalkyl. cyano. nitro. CHO, CH=NOR5, CM alkylcarbonyl. CM alkoxycarbonyl or SFj; or together R1 and R2 form a five or six numbered saturated or unsaturaled carbocyclic ring, opdonally subsdruted by one or two CM alkyl groups; R1 is hydrogen, CM alkyl, CH2(CM haloalkyl). CM cyanoalkyl, CM alkenyl. CM alkynyl. CM alkoxy(C,. ,)alkyl, CM alkylthio(C,^)alkyl. CM alkoxy(CMWkoxy(CM)aIkyt. CM alkylcarbonyl, CM alkoxycarbonyl. formyl, CM alkylcarbonyl(CM)alkyl. CM alkoxycarbonyl(CM)alkyI, CMalkylaminocarbonyl. di(C,. t)alkylaminocarbonyl, optionally subsututed phenoxycarbonyl, opdonally subsututed phenyl(Ci^)alkyl or wherein X is O or S; n is 0 or 1; Y is O. S or NR7; R' is hydrogen, halogen, CM alkyl. CM haloalfcyl, CM S(O),R'; R* is hydrogen, halogen, cyano, CM alkyl, CM haloalkyl, CM cyanoalkyl, CM alkcnyl. Cw alkoxy. CM haloalkoxy. CM alkyllhio. CM haloalkylthio, CM cycloalkyl, CM alkoxy(CM>alkyl or SFS; R: alkynyt, CM cycloalkyl. CM halocycloalkyl. CM cyanocycloalkyl. C,.,alkyl(CM)cycloalkyl. C,.3 alfcyl(d- 7)halocycloalkyl. CM cycloalkyl(Ci-»)alkyl. CM cycloalkenyl, CM cycloalkenyl(CM)alkyl. CM haloalku^ d_icyanoalkcnyl. CM aUcoiy(C,^)alkyl. formyl, CM carboxyalkyl. CM alkylcarbonyl(CM)alkyl, CM alkoxycarbonyl(CM)alkyl, CM a!kylthio(CM)alkyl. CM alkylsulfmyl(CM)atkyl. CM alkylsulfonyKd. t)alkyl, «minocarbonyl(CM)alkyl. CMalkylaminocarbonyl(CM)alfcyl. di(CM)alkylaminocarbonyl(C,. i)alkyl, CM alkoxycarbonyl, CM alkylcarbonyl, aminocarconyl. CM alkylaminocarbonyl, di(Ci. <)alkylaminocarbonyl. opdonally subsdtuted phenyl, opdonally substituted phenyl(CM)alkyl, opdonally subsututed phenyUCwialkenyi, opdonally subsdtuted heteroaryl, opuonally subsututed heteroaryl(C|. 4)alkyl. opdonally subsdtuted hctcrocyclyl, optionally subsdtuted heterocyclyl(CM)alkyl, a group OR1, a group SH, a group S(Oyi', a group NR'V or a group C(R")=NOR'!; RJ is hydrogen. CM alkyl. opuonally subsututed phenyl or opdonally substituted phcnyKd j)alkyl; R* is CM alkyl. CM haloalkyl or opdonally subsutuled phenyl: R7 is hydrogen, cyano, CM alkyl, CM haloalkyt, CM cyanoalkyl, CM alkcnyl. CM alkynyl. CM cycloalkyl, CM haloalkenyl. CM cycloalkyl(CM)alkyl. CM alkoxy(d-i)alkyl. Ci4 alkoxycarbonyl. CM alkylcarbonyl. CMalkylaminocarbonyl, di(d.i)alkyUmtnocarbonyl, opdonally substituted phenyl or opuonally subsututed heteroaryl: R* is hydrogen, CM alkyl. CM haloalkyl, CM alkenyl. CM cyinoalkyl. CM alkoxycarbonyKC, Jalkyl. opdonally substituted phenyl. opdonally subsututed phenyl(d-<)alkyl. opdonally subsututed heteroaryl. N=C(CHj)i: R* is CM alkyl. C,_i haloalkyl. CM alkenyl, cyano, CM cyanoalkyl, CM alkoxycarbonyKd-Oalkyl, opuonally subsdtuted phenyl. opuonally subsdruted phenyl(d-<)*lkyl or opuonally subsdtuted heteroaryl: R'° and R" are. independently, hydrogen. CM alkyl, CM cycloalkyl, CM alkenyl. CM alkynyl. CM haloalkyl. CM alkoxy(CM)alkyl. CM alkoxycarbonyl, optionally subsdruted phenoxycarbonyl. formyl. CM alkylcarbonyl. CM alkylSCh. opuonally subsututed phenylSOj or optionally subsututed phenyl(CM)alkyl; R'! is C|.j alkyl; R" is CM alkyl, opuonally subsututed phenyl(C|.2)alkyl; and p and q are. independently, 0, I or 2.
Description
BENZAZOLES: BENZOXAZOLE, BENZTHI AZOLE AND BENZIMIDAZOLE DERIVATIVES
The present invention relates to isothiazole derivatives, to processes for preparing them, to fungicidal, insecticidal, acaricidal, molluscicidal and nematicidal compositions comprising them, to methods of using them to combat fungal diseases (especially fungal diseases of plants) and to methods of using them to combat and control insect, acarine, mollusc and nematode pests.
Isothiazole derivatives are disclosed in WO 95/31448, WO 97/18198, WO 98/02424 and WO 98/05670.
The present invention provides a compound of formula (I):
wherein X is 0 or S; n is 0 or 1; Y is 0, S or NR7; R1 is hydrogen, halogen, CM alkyl, C1j5 haloalkyl, alkoxy, C,^ haloalkoxy, C,^ alkylthio, C,^ haloalkylthio, Cw cycloalkyl, C,^ alkoxy(C,Jalkyl or SF5; R2 is hydrogen, halogen, Cw alkyl, Cw alkoxy, haloalkoxy, alkylthio, CM haloalkylthio, Cw alkylsulfinyl, C,^ haloalkylsulfinyl, C,^ alkylsuifonyl, Cw haloalkylsulfonyl, haloalkyl, cyano, nitro, CHO, CH=NOR5, C,^ alkylcarbonyl, aikoxycarbonyl or SF5; or together R1 and R2 form a five or six membered saturated or unsaturated carbocyclic ring, optionally substituted by one or two C,^ alkyl groups; R3 is hydrogen, C,^ alkyl, CH2(CM haloalkyl), C,^ cyanoalkyl, C3^ alkenyl, alkynyl, C,^ alkoxy(C, Jalkyl, alkylthio(C,Jalkyl, C,4 aIkoxy(C, Jalkoxy(C, Jalkyl, alkylcarbonyl, C,^ aikoxycarbonyl, formyl, Cw alkylcarbonyl(C^)alkyl, alkoxycarbonyl(CM)alkyl, C^alkylaminocarbonyl, di(C,^)alkylaminocarbonyl, optionally substituted phenoxycarbonyl, optionally substituted phenyl(CM)alkyl or S(O)qR6; R4 is hydrogen, halogen, cyano, alkyl, haloalkyl, Cw cyanoalkyl, CM alkenyl, alkynyl, C3.7 cycloalkyl, C3.7 halocycloalkyl, C3.7 cyanocycloalkyl, C,.3 alkyl(C3.7)cycloalkyl, C,.3alkyl(C3.7)halocycloalkyl, Cw cycloalkyl(C,Jalkyl, C5^ cycloalkenyl, C5^ cycloalkenyl(CM)alkyl, haloalkenyl, C^cyanoalkenyl, C,^ alkoxy(C, Jalkyl, formyl, C,. 6 carboxyalkyl, C,^ alkylcarbonyl(C,^)alkyl, C,^ alkoxycarbonyl(C, Jalkyl, alkylthio(C,.
6)alkyl, C,^ alkylsulfmyl(C,^)alkyI, CM alkylsulfonyl(C^)alkyl, aminocarbonyl(CM)alkvl. C,^alkylaminocarbonyl(C,^)alkyl, di(CM)alkylaminocarbonyl(C,^)alkyl, C,^ alkoxycarbonyl, alkylcarbonyl, aminocarbonyl, CM alkylaminocarbonyl, di(C,_ 6)alkylaminocarbonyl, optionally substituted phenyl, optionally substituted phenyl(CM)alkyl, optionally substituted phenyl(C2_4)alkenyl, optionally substituted heteroaryi, optionally substituted heteroaryl(CM)alkyl, optionally substituted heterocyclyi, optionally substituted heterocyclyl(CM)alkyl, a group OR8, a group SH, a group S(O)pR9, a group NR10R“ or a group C(R12)=NOR13; R5 is hydrogen, C,^ alkyl, optionally substituted phenyl or optionally substituted phenyl(CM)alkyl; R6 is Cw alkyl, haloalkyl or optionally substituted phenyl; R7 is hydrogen, cyano, Ckg alkyl, haloalkyl, cyanoalkyl, C2^ alkenyl, C2^ alkynyl, C3.7 cycloalkyl, C2^ haloalkenyl, C3^ cycloalkyl(C,^)alkyl, C,^ alkoxy (C^alkyl, Cu alkoxycarbonyl, C,^ alkylcarbonyl, Cw alkylaminocarbonyl, di(CM)alkylaminocarbonyl, optionally substituted phenyl or optionally substituted heteroaryi; R8 is hydrogen, C,^ alkyl, CM haloalkyl, C3^ alkenyl, CM cyanoalkyl, alkoxycarbonyl(Cw)alkyl, optionally substituted phenyl, optionally substituted phenyl(CM)alkyl, optionally substituted heteroaryi, N=C(CH3)2; R9 is C,^ alkyl, Cw haloalkyl, C3^ alkenyl, cyano, CM cyanoalkyl, C,^ alkoxycarbonyl(C]^)alkyl, optionally substituted.phenyl, optionally substituted phenyl(C,. 4)alkyl or optionally substituted heteroaryi; R’° and R" are, independently, hydrogen, CM alkyl, C3.7 cycloalkyl, Cw alkenyl, C3^ alkynyl, haloalkyl, C,^ alkoxy(Cw)alkyl, C,^ alkoxycarbonyl, optionally substituted phenoxycarbonyl, formyl, C,^ alkylcarbonyl, C,^ alkylSO2, optionally substituted phenylSO2 or optionally substituted phenyl(CM)alkyl; R12 is C,.3 alkyl; R13 is C,^ alkyl, optionally substituted phenyl(C,.2)alkyl; and p and q are, independently, 0,1 or 2.
The compounds of formula (I) may exist in different isomeric or tautomeric forms. This invention covers all such isomers and tautomers and mixtures thereof in all proportions.
In a further aspect the present invention provides a compound of formula (I) wherein X is O or S; n is 0 or 1; Y is 0, S or NR7; R1 is hydrogen, halogen, C,^ alkyl,' C,^ haloalkyl, alkoxy, C,^ haloalkoxy, C,^ alkylthio, C3^ cycloalkyl or C,^ alkoxy(Cw)alkyl; R2 is hydrogen, halogen, C,^ alkyl, haloalkyl, cyano, nitro, CHO, CH=N0R5, C,^ alkylcarbonyl, C,^ alkoxycarbonyl or C,^ alkylS(O)x; or together R1 and R2 form a five or six membered saturated or unsaturated carbocyciic ring, optionally substituted by one or two C,^ alkyl groups; R3 is hydrogen, Cw alkyl, CH2(CW haloalkyl), Cw alkenyl, Cw alkynyl, C,^ alkoxy(C,^)alkyl, C,^ alkylcarbonyl, C,^ alkoxycarbonyl, formyl, optionally substituted phenoxycarbonyl, optionally substituted phenyl(CM)alkyl or S(O)yR25; R4 is hydrogen, halogen, cyano, optionally substituted alkyl, CM alkoxy, haloalkoxy, C|.8 alkylthio, alkenyl, CM alkynyl, C3.7 cycloalkyi (optionally substituted with halogen or C,^ alkyl), C5^ cycloalkenyl (optionally substituted with halogen or alkyl), C2^ haloalkenyl, NHSO,R24, NHCOR24, CONR20R21, NR20R21, COR24, CO,R20, optionally substituted phenyl, optionally substituted heteroaryl or a group ZR26; R5 is hydrogen, C,^ alkyl, optionally substituted phenyl or optionally substituted phenyl(CM)alkyl; R25 is alkyl, C,^ haloalkyl or optionally substituted phenyl; Z is 0, S, SO, S02 or NR27; R7 is hydrogen, cyano, C,^ alkyl, haloalkyl, C,^ cyanoalkyl, Cw alkenyl, Cw alkynyl, C3.7 cycloalkyi, Cw haloalkenyl, C3. 6 cycloalkyl(Cw)alkyl, CM alkoxy(C^)alkyl, alkoxycarbonyl, C,^ alkylcarbonyl, C,^ alkylaminocarbonyl, di(Cw)alkylaminocarbonyl, optionally substituted phenyl or optionally substituted heteroaiyl; R26 and R27 are, independently, hydrogen, C,.8 alkyl, C3^ alkenyl, C3^ alkynyl, C,^ alkoxy(Cw)alkyl, C,^ alkoxycarbonyl, optionally substituted phenoxycarbonyl, C,^ alkylcarbonyl or optionally substituted phenyl(CM)alkyl, or R26 and R27 join to form a 5-or 6-membered saturated or unsaturated ring optionally containing another heteroatom selected from oxygen, sulfur and nitrogen; R20 and R21 are, independently, hydrogen or C,^ alkyl; R24 is C,^ alkyl or phenyl; and x and y are, independently, 0, 1 or 2.
Alkyl is straight or branched chain and is, for example, methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, fro-propyl, n-butyl, .sec-butyl, fro-butyl, Zeri-butyl or neo-pentyl.
Halogen is fluorine, chlorine, bromine or iodine.
Haloalkyl groups are alkyl groups which are optionally substituted with one or more of the same or different halogen atoms and are, for example, CF3, CH2CF3 or CH2CHF2.
Phenyl(CM)alkyl is, for example, 1-phenyleth-l-yl, 2-phenyleth-l-yl, 2-phenylprop-2-yl, 3-phenylprop-l-yl, but is preferably benzyl.
The term heteroaryl refers to an aromatic ring containing one or more heteroatoms (preferably one or two heteroatoms) selected from 0, S and N. Examples of such rings include pyridine, pyrimidine, furan, quinazoline, thiophene, thiazole, oxazole and isoxazole.
The term heterocyclyl refers to a non-aromatic ring containing one or more (preferably one or two) heteroatoms selected from 0, S and N. Examples of such rings include 1,3-dioxolanyl, tetrahydrofuryl and morpholinyl. It is preferred that heterocyclyl is optionally substituted by C,^ alkyl.
Cycloalkenyl includes cyclopentenyl, cyclohexenyi and cyclohexadienyl.
It is preferred that phenyl moieties and heteroaryl groups are optionally substituted by one or more substituents independently selected from halogen, C,^ alkyl, C,^ haloalkyl, C,^ alkoxy(C,^)alkyl, C,^ alkoxy, CM haloalkoxy, alkylthio, C,^ haloalkylthio, C,^ alkylsulfinyl, C,^ haloalkylsulfinyl, alkylsulfonyl, C,^ haloalkylsulfonyl, C2^ alkenyl, C2^ haloalkenyl, C2^ alkynyl, C3^ cycloalkyi, nitro, cyano, CO,H, C,^ alkylcarbonyl, alkoxycarbonyl, R14RI5N or R16R17NC(O); wherein R14, R15, R16 and R17 are, independently, hydrogen or Cw alkyl.
It is preferred that R1 is C,.2 alkyl, especially, methyl.
It is preferred that R2 is hydrogen, cyano or halogen, especially, halogen (especially bromo or chloro).
It is preferred that R3 is hydrogen, Cw alkyl or Cw alkoxy(Cw)alkyl.
It is further preferred that R3 is hydrogen, ethyl or ethoxymethyl.
It is preferred that R4 is alkoxy(C1.6)alkyl, C,^ haloalkyl, (C,^ alkyl)amino, di- (CM alkyl)amino (such as N(C2H5)2 or N(C2H5) (CH[CH2]CH3)), morpholino, C,^ alkyl or alkoxy, especially morpholino, alkyl or C,^ alkoxy.
It is preferred that n is 0.
It is preferred that X is oxygen.
It is preferred that Y is oxygen or sulphur.
It is preferred that the compounds of the invention are of formula (la).
In one particular aspect the present invention provides a compound of formula (la) wherein R1 is CM alkyl (especially methyl or ethyl); R2 is hydrogen, halogen (especially chloro or bromo) or cyano; or R1 and R2 together form a cyclopentyl, cyclohexyl or phenyl ring; R3 is hydrogen, CM alkyl (especially methyl or ethyl), alkenyl (especially allyl), C,. 6 alkynyl (especially propargyl), or C,^ alkoxy(Cw)alkyl (especially methoxymethyl and ethoxymethyl); n is 0; X and Y are both oxygen; and R4 is Cw alkyl [optionally substituted with halogen, CM alkoxy, CM alkylthio, CM haloalkylthio, alkylamino, dialkylamino (wherein the alkyl groups may form part of a five or six-membered ring, optionally containing one heteroatom such as oxygen or nitrogen), phenyl (itself optionally substituted with halogen), C3^ cycloalkyl, Cw alkenyl, C3^ alkynyl, C^ cycloalkyl, phenyl [optionally substituted with halogen, CM haloalkyl (especially CF3), nitro, CO2H, or cyano] or heteroaryl (especially pyridyl or pyrimidinyl) [optionally substituted with CM alkyl or CM haloalkyl]].
In one particular aspect the present invention provides a compound of formula (la) wherein R1 is CM alkyl (especially methyl or ethyl); R2 is hydrogen, halogen (especially chloro or bromo) or cyano; or R1 and R2 together form a cyclopentyl, cyclohexyl or phenyl ring; R3 is hydrogen, CM alkyl (especially methyl or ethyl), phenyl(CM)alkyl (especially benzyl), Cw alkylcarbonyl (especially acetyl) or CM alkylsuifonyl (especially methanesulfonyl); n is 0; X is oxygen; Y is oxygen or sulphur (especially oxygen); R4 is hydrogen, C,.g alkyl [optionally substituted with halogen, CM alkoxy, CM alkylS(O)ra, phenyl (itself optionally substituted with halogen), phenoxy, NR20R21, CO;H, CONR22R23, cyano, C3. 6 cycloalkyl or CO(C,^ alkoxy)], C,.g alkoxy (optionally substituted with halogen), C,.g alkylthio, C2.g alkenyl (optionally substituted with halogen), NHSO2R24, NHCOR24, NR2OR21, COR24, CO2R20, C2.g alkynyl, cycloalkyl (optionally substituted with halogen or C,^ alkyl), C^ cycloalkenyl, phenyl [optionally substituted with halogen, CM haloalkyl (especially CF3), CM alkoxy, nitro, CO2R20 or cyano] or heteroaryl (especially pyridyl, pyrimidinyl, furanyl or thiophenyl) [optionally substituted with C,^ alkyl, nitro or CM haloalkyl]; R20, R21, R22 and R23 are, independently, hydrogen or CM alkyl; R24 is CM alkyl 01 phenyl; and m is 0, 1 or 2.
The physical parameter concerns the relative solubility of a compound in n-octanol and water and, for a compound [A]:
In a further aspect the present invention provides a compound of formula (I) wherein log^K^ (calculated using the CLOGP3 program, available from BioByte Corp.,201 West 4th Street, Suite 204, Claremont, CA 91711, USA) of the compound is in the range zero to 8, preferably in the range 1 to 6 and more preferably in the range 1.2 to 5.2.
It will readily be seen that the side chain portion of formula (XIX):
(XIX) is a portion of a compound of formula (I). The longest bond path of the side chain portion of formuia (XIX) is the path involving the minimum number of bonds from the carbon labelled # to the furthest atom of the side chain, having an atomic weight greater than 10 Daltons. If there is more than one longest bond path, each involving the same minimum number of bonds, there is a set of longest bond paths.
In a further aspect of the present invention it is preferred that R4 is hydrogen, SH, C,^ alkyl, C3^ cycloalkyl, C2^ alkenyl, C2.5 alkynyl, Cw haloalkyl, CM cyanoalkyl, Cw haloalkenyl, optionally substituted heterocyclyl(CM)alkyl, C2^ cyanoalkenyl (such as 1-cyano-2-methylpropenyl), phenyl (optionally substituted with fluoro, chloro, bromo, nitro, cyano, C,^ alkyl, C,.2 alkoxy, CM haloalkyl (such as trifluoromethyl), CM haloalkoxy (such as trifluoromethoxy), methanesulfonyl, methylenedioxy or di(CM alkyl)amino (such as dimethylamino)), phenyl(Cb3)alkyl (phenyl optionally substituted with halogen, nitro, cyano, C,^ alkyl, C,.2 alkoxy, CM haloalkyl (such as trifluoromethyl), CM haloalkoxy (such as trifluoromethoxy), methanesulfonyl, or methylenedioxy), formyl, optionally substituted heterocyclyi, optionally substituted heteroaryi, optionally substituted heteroaryl(CM)alkyl, Cj.2 alkylcarbonyl, CM alkoxy carbonyl, C,.5 alkoxycarbonyl(CM)alkyl, a group NR‘°R", a group OR8, CM alkoxymethyl, chlorine, a group SR9, or a group C(Rl2)=NOR13; R8 is hydrogen, C|.3 alkyl, CM haloalkyl (such as 2,2,2-trifluoroethyl), C2M alkenyl (such as allyl), phenyl (optionally substituted with fluoro, chloro, bromo, nitro, cyano, alkyl, C,.2 alkoxy, CM haloalkyl (such as trifluoromethyl), CM haloalkoxy (such as trifluoromethoxy), methanesulfonyl, or methylenedioxy), phenyl(CH2) (phenyl optionally substituted with fluoro, chloro, bromo, nitro, cyano, alkyl, C,.2 alkoxy, CM haloalkyl (such as trifluoromethyl), CM haloalkoxy (such as trifluoromethoxy), methanesulfonyl, or methylenedioxy), N=C(CH3)2; R9 is C,.5 alkyl, phenyl (optionally substituted with fluoro, chloro, bromo, nitro, cyano, CM alkyl, C,.2 alkoxy, CM haloalkyl (such as trifluoromethyl),
CM haloalkoxy (such as trifluoromethoxy), methanesulfonyl, methylenedioxy or di(C,_, alkyl)amino (such as dimethylamino)), C,.2 haloalkyl, cyano, cyanomethyl or C,.2 alkoxycarbonylmethyl; R’° and R11 are, independently, hydrogen, CM alkyl, C5^ cycloalkyi, formyl, C,_3 alkylcarbonyl, phenoxycarbonyl, C,.2 alkylSO2 or phenylSO2; R12 is C,.2 alkyl; R 13 is C,.2 alkyl or benzyl; heterocyclyl is, for example, tetrahydrofuryl, 1,3-dioxolanyl or morpholinyl; an example of an optional substituent for heterocyclyl is CM alkyl; heteroaryl is, for example, thienyl, furyl, pyridyl, quinazolinyl, pyrazolyl or isoxazolyl; and examples of optional substituents for heteroaryl include Cw alkyl, C,^ haloalkyl and phenoxy.
In a further aspect the present invention provides a compound of formula (I) wherein the side chain portion of formula (XIX) is such that each atom having an atomic weight greater than 10 Daltons in the side chain portion is no more than four bond lengths away from any of the atoms present in the longest bond path or one of the longest bond paths.
In another aspect the present invention provides a compound of formula (la) or (lb) wherein R1 is C,.2 alkyl, chloro, CF3, OCH3 or SCH3; R2 is hydrogen, halogen (such as fluorine, chlorine or bromine), cyano, nitro, CMalkyl (such as methyl), CM alkoxy (such methoxy) or SCH3; or R1 and R2 join to form a C3.7 cycloalkyi (such as cyclopentyl or cyclohexyl) or phenyl ring; R3 is hydrogen, C,^ alkyl optionally substituted with cyano, halogen, (C^jalkoxy, (C^jalkoxyiC^jalkoxy, Cwalkoxycarbonyl, phenyl or CMalkylthio (such as methyl, ethyl, n-propyl, fro-propyl, cyanomethyl, 2,2,2-trifluoroethyl, (C,. 2)alkoxymethyl, methoxyethoxymethyl, methoxycarbonylmethyl, phenylmethyl or methylthiomethyl), alkenyl (such as allyl), alkynyl (such as propargyl), carbonyl substituted with C,^alkoxy, CMalkylamino or di(CMalkyl)amino (such as C,.2 alkoxycarbonyl, methylaminocarbonyl or dimethylaminocarbonyl), CMalkylthio (such as methylthio) or phenylthio; X is oxygen or sulphur; Y is oxygen, sulphur or NR7; n is 0; R4 is hydrogen, SH, C,^ alkyl, C3^ cycloalkyi, alkenyl, C2.5 alkynyl, CM haloalkyl, CM cyanoalkyl, C2^ haloalkenyl, optionally substituted heterocyclyl(CM)alkyl, l-cyano-2-methylpropenyl, phenyl (optionally substituted with fluoro, chloro, bromo, nitro, cyano, C,.2 alkyl, ierZ-butyl, C,.2 alkoxy, trifluoromethyl, trifluoromethoxy, methanesulfonyl, methylenedioxy or dimethylamino), phenyl(C,.3)alkyl (phenyl optionally substituted with fluorine), formyl, optionally substituted heteroyclyl, optionally substituted heteroaryl, optionally substituted heteroaryl(CM)alkyl, C,.2 alkylcarbonyl, CM alkoxycarbonyl, C,_5 alkoxycarbonyl(CM)alkyl, a group NR10Rn, a group OR8, CM alkoxymethyl, chlorine, a group SR9, or a group C(R12)=NOR13; R7 is hydrogen or CMalkyl (such as methyl); R8 is hydrogen, C,.s alkyl, 2,2,2-trifluoroethyl, allyl, phenyl (optionally substituted with chloro), phenyl(CH2) (phenyl optionally substituted with fluoro, chloro), N=C(CH3)2; R9 is C,.3 alkyl, phenyl, C,.2 haloalkyl, cyano, cyanomethyl or C,.2 alkoxycarbonylmethyl; R’° and Ru are, independently, hydrogen, CM alkyl, C5^ cycloalkyl, formyl, C,.3 alkylcarbonyl, phenoxycarbonyl, C,.2 alkylSO2 or phenylSO2; R12 is C,.2 alkyl; R13 is C,.2 alkyl or benzyl; heterocyclyl is, for example, tetrahydrofuryl, 1,3-dioxolanyl or morpholinyl; an example of an optional substituent for heterocyclyl is CM alkyl; heteroaryl is, for example, thienyl, furyl, pyridyl, quinazolinyl, pyrazolyl or isoxazolyl; and examples of optional substituents for heteroaryl include C,^ alkyl, haloalkyl and phenoxy. Specific preferred values of R4 ar-. recited in Table A1.
The compounds in the following Tables illustrate compounds of the invention. Table Al provides 352 compounds of formula (la) wherein R1 is methyl; R2 is hydrogen; R3 is hydrogen; X and Y are each oxygen; n is 0; and R4 is as defined in the Table. TABLE Al
Compound Number R4
1 H 2 CH3 3 CH2CH3 4 CH2CH2CH3 5 CH2CH2CH2CH3 6 CH2CH2CH2CH2CH3 7 CH2CH2CH2CH2CH2CH3 8 CH(CH3)2 9 C(CH3)3 10 CH(CH3)CH2CH3 11 CH2CH(CH3)CH2CH3 12 CH(CH3)CH2CH2CH3 13 CH(CH2CH3)2 14 CH2CH(CH3)2 15 CH2C(CH3)3 16 CH2CH2CH(CH3)2 17 CH2CH2C(CH3)3 18 C(CH3)2CH3 19 C(CH3)2CH2CH3 20 C(CH3)2CH2CH2CH3 21 cyclopropyl 22 l-methylcyclopropyl 23 2-methylcyclopropyl 24 1 -cyanocyclopropyl 25 2,2-dichloro-3,3-dimethy lcyclopropyl 26 2,2-dichloro-l-ethyl-3-methylcyclopropyl 27 cyclobutyl 28 cyclopentyl 29 1-methylcyclopentyl 30 1-cyclopentenyl 31 2-cyclopentenyl 32 3-cyclopentenyl 33 2-cyclopentenylmethyl 34 1-cyclopentenylmethyl 35 cyclohexyl 36 1-methylcyclohexyl 37 1-cyclohexenyl 38 2-cyclohexenyl 39 cyclohexylmethyl 40 2-cyclohexenylmethyl 41 cyclopropylmethyl 42 cyclopentylmethyl 43 2-cyclopentylethyl 44 CH=CH2 45 CH=CHCH3 46 CH=C(CH3)2 47 C(CH3)=CHCH3 48 CH=CHCH2CH2CH3 49 C(CH3)=C(CHj)2 50 CH=CHCH(CH3)2 51 CH2CH=CH2 52 CH2CH=CHCH3 53 CH2CH=C(CH3)2 54 CH2C(CH3)=CH2 55 CH2C(CH3)=CHCH3 56 CH2C(CH3)=C(CH3)2 57 CH2CH2CH=CH2 58 C(CH3)=CHCH3 59 C(CH3)2CH=CH2 60 C(CH3>CHCH2CH3 61 CH=CHCH=CHCH3 62 cyclopentyldienyl 63 4-nitrostyryl
64 C=CH 65 C=CCH3 66 CsCCH2CH3 67 ru r=ru
68 CH(CH3)OCH
69 C(CH3)2ChCH 70 ch2ch2c=ch 71 CH2CH2ChCCH3 72 CH2CH2COCH3 73 ch2f 74 chf2 73 CF3 76 CF(CH3)2 77 ch2cf3 78 cf2cf3 79 cf2chf2 80 cf2cf2cf3 81 cf2cf2cf2cf3 82 cf=cfcf2cf3 83 CF2C1 84 CF2Br 85 CFC1CF3 86 CF2CF2C1 87 CF2CFC1CF3 88 CFBrCF3 89 CH2C1 90 CH2CH2C1 91 CH2CH2CH2C1 92 CH2CH2CH2CH,C1 93 CH(C1)CH3 94 CH(C1)-C6H5 95 CH(C1)CH2CH3 96 CH(C1)CH2C1 ’’ CC1(CH3): 98 c(ch3)2ch2ci 99 CHClj 100 C(CH2C1),CH, CfCH^CHCl, CH2CH(C1)CH3 103 CC13 CCliCCl, IU3 CH=CHC1 106 CC1=CH, ίθ8 CC1=CC12 1US CH2Br 109 CHBr, !!“ C(CH,)2Br " CH(Br)CH(CH3), j C(CH3)BrCH2Br 114 CH’™
114 CH2CH2CN
115 CH(CH3)CN
116 C(CH3),CN
117 CH2CH(CH3)CN
118 CH2C(CH3)2CN 119 C(CN)=C(CH3)2 120 CH2CO2CH3 121 CH2CO2CH2CH3 122 CH2CO2C(CH3)3 123 CH(CH3)CO2CH3 124 CH(CH3)CO2CH2CH3 125 CH(CH3)CO2C(CH3)3 126 C(CH3)2CO2CH3 127 C(CH3)2CO2CH2CH3 128 C(CH3)2CO2C(CH3)3 129 CH2C(CH3)2CH2CO2CH2CH3 130 CH2OCH3 131 CH2OCH2CH3 132 CH2CH2OCH3 133 CH2OCH(CH3)2 134 CH2OC(CH3)3 135 C(CH3)2OCOCH3
136 C(CH3)2OH 137 CH2OCH2CH2OCH3 138 CH2OCH2CH2OCH2CH3
139 CH2CH2OH 140 CH2O-C6H5 141 CH(CH3)O-C6H5 142 1 -methyl-1 -(4-chlorophenoxy)ethyl 143 2-nitrophenoxymethyl 144 4-nitrophenoxymethyl 145 2-tetrahydrofuryl 146 3-tetrahydrofuryl 147 2-tetrahydrofurylmethyl 148 3-tetrahydrofurylmethyl 149 (l,3-dloxolan-2-yl)methyl 150 (2 -methyl-1,3-dioxolan-2-yl)methyl 151 (l,3-dioxolan-4-yl)methyl 15 2 (2-methyl-1,3 -dioxolan-4-y l)methyl
153 CHO 154 COCH3 155 COCH2CH3 156 CO2CH3 157 CO2CH2CH3 158 CO2CH(CH3)2 159 CO2C(CH3)3 160 CO2C(CH3)2CH2CH3
161 CH2CH2CO2H 162 CH2CH2CO2CH3 163 CH2CH2CO2CH2CH3 164 CH2CH2CH2CO2CH3 165 CH2CH2CH2CO2CH2CH3
166 CH=NOH 167 C(CH3)=NOCH3
168 C(CH3)=NOH 169 " C(CH3)=NOCH3 170 C(CH3)=NOCH2-C6H5 171 CH2SCH3 172 CH2CH2SCH3 173 CH2S-C6H5 174 Cl 175 NH2 176 NHCH3 177 NHCH2CH3 178 NHCH2CH2CH3 179 N(CH3)2 180 N(CH3)CH,CH3 » 181 N(CH2CH3)2 182 NHCH(CH3)2 μ 183 NHC(CH3)3 184 N(CH3)CH(CH3)2 7 185 N(CH3)C(CH3)3 186 NH-cyclopentyl x; 187 NH-cyclohexyl 188 N(CH3)-cyclopentyl 189 N(CH3)-cyclohexyl 190 N(CH2CH3)-cyclohexyl 4‘.: 191 morphoiino
» 192 NHCHO 193 NHCOCH3 194 NHCOCH2CH3 195 NHCOCH(CH3)2 196 NHCO-C6H5
197 N(CH3)CHO 198 N(CH3)COCH3 199 N(CH3)COCH2CH3 200 NHSO2CH3 201 NHSO2CH2CH3 202 NHSO2-C6H5 203 OCH3 204 OCH2CH3 205 OCH2CH2CH3 206 OCH(CH3)2 207 OC(CH3)3 208 OCH.CHfCH,), 209 OCH(CH3)CH2CH3 210 OCH,CF3 211 OCH2C(CH3)3 212 OCH2-C6H5 213 4-fluorobenzyloxy 214 2,4-dichlorobenzyloxy 215 OCH2CH=CH2 216 O-C6Hj 217 2-chlorophenoxy 218 4-chlorophenoxy 219 O-N=C(CH3)2 220 SCH3 221 SCH2CH3 222 S(CH2)2CH3 223 SCH(CH3)2 224 SC(CH3)3 225 SCH2CH(CH3)2 226 SCH2C(CH3)3 227 S-C6H5
228 SCH,CN 229 SCH2CO2CH3 230 SCH2CO2CH2CH3 231 SCHF2 232 SCF3 233 SCH2CF3
234 SCF2CF2H
235 SCN 236 CH2C6H5 237 CH(CH3)C6H5 238 C(CH3)2C6H5 239 CH2C6F5 240 3,5-diF-C6H3 241 3-CH3O-C6H4 242 4-F-C6H4 243 4-F-C6H4 244 2,6-diCl-4-CF3-C6H2 245 CH(CH2CH3)C6H3 246 CH(C6H3)2 247 CH2CH2C6H3 248 C6H3 249 2-Br-C6H4 250 3-Br-C6H4 251 4-Br-C6H4 232 4-ier/-butyl-C6H4 253 2-Cl-C6H4 234 3-Cl-C6H4 255 4-Cl-C6H4 256 2,3-diCl-C6H3 257 2,4-diCl-C6H3 258 2,5-diCl-C6H3 259 2,6-diCl-C6H3 260 3,4-diCl-C6H3 261 3,5-diCl-C6H3 262 2,4,6-triCl-C6H2 263 C6C15 264 2-Cl-4-F-C6H3 265 2-Cl-6-F-C6H3 266 4-Cl-2,5-diF-C6H2 267 2-Cl-4-NO2-C6H3 268 2-Cl-4-CF3-C6H3 269 2-Cl-6-CF3-C6H3 270 2-Cl-4-methanesulfonyl-C6H3 271 2,4-diCl-5-F-C6H2 272 2-F-C6H4 273 3-F-C6H4 274 4-F-C6H4 7, 275 2,3-diF-C6H3 ., 276 2,4-diF-C6H3 '? 277 2,5-diF-C6H3 ... 278 2,6-diF-C6H3 ; 279 3,4-diF-C6H3 .... 280 3,5-diF-C6H3 .7 281 2,3,4-triF-C6H2 Z 282 2,3,5-triF-C6H2 283 2,3,6-triF-C6H2 .* 284 2,4,6-triF-C6H2 > 285 3,4,5-triF-C6H2
286 2,3,4,5-tetraF-C6H 287 C6F5 288 2-F-3-CF3-C6H3 289 2-F-4-CF3-C6H3 290 2-F-5-CF3-C6H3 291 2-F-6-CF3-C6H3 292 4-F-2-CF3-C5H3 293 4-F-3-CF3-CsH3 294 5-F-2-CF3-C6H3 295 .,. 2-CN-C6H4 296 3-CN-C6H4 297 4-CN-C6H4 298 4-dimethylaminophenyl 299 2-C2H5O-C6H4 300 3-C2H5O-C6H4 301 4-C2H5O-C6H4 302 2-C2H5-C6H4 303 3-C,H5-C6H4 304 4-C2Hj-C6H4 305 2-CH3O-C6H4 306 3-CH3O-C6H4 307 4-CH3O-C6H4 308 3,4-diCH3O-C6H3 309 3,5-diCH3O-C6H3 310 2,6-diCH3O-C6H3 311 3,4-(methylenedioxy)phenyl 312 2-CH3-C6H4 313 3-CH3-C6H4 314 4-CH3-C6H4 315 2,3-diCH3-C6H3 316 2,4-diCH3-C6H3 317 2,5-diCH3-C6H3 318 2,6-diCH3-C6H3 319 3,4-diCH3-C6H3 320 2,4,6-triCH3-C6H2 321 2-NO2-C6H4 322 3-NO2-C6H4 323 4-NO2-C6H4 324 4-methanesulfonyl-2-nitrophenyl 325 3-trifluoromethoxyphenyl 326 2-trifluoromethylphenyl 327 3-trifluoromethylphenyl 328 4-trifluoromethylphenyl 329 4-carboxymethylphenyl 330 2-thienyl 331 3-chloro-2-thienyl 332 3,4,5-trichloro-2-thienyl 333 2-benzothiophenyl 334 2-thienylmethyl 335 5-tert-butyl-2-furyl 336 5-nitro-2-furyl 337 pyridin-2-yl 338 pyridin-3-yl 339 pyridin-4-yl 340 3-chloro-2-pyridyl 341 6-chloro-2-pyridyl 342 2,6-dichloro-4-pyridyl 343 2-chloro-3-pyridyl 344 2-phenoxy-3-pyridyl 345 2-quinazolinyl 346 4-biphenyl 347 l,3-dimethyl-5-pyrazolyl 348 4-chloro-l,3-dimethyl-5-pyrazolyl 349 5-isoxazolyl 350 6-trifluoromethyl-2-pyridyl
351 OH
352 SH TABLE A2
Table A2 provides 352 compounds of formula (la) wherein R1 is methyl; R2 is fluoro; R3 is hydrogen; X and Y are each oxygen; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE A3
Table A3 provides 352 compounds of formula (la) wherein Rl is methyl; R2 is chloro; R3 is hydrogen; X and Y are each oxygen; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table A1. TABLE A4
Table A4 provides 352 compounds of formula (la) wherein R1 is methyl; R2 is bromo; R3 is hydrogen; X and Y are each oxygen; n is 0; and the values of R4 match those of the Correspondingly numbered compounds of Table Al. - TABLE A5
Table A5 provides 352 compounds of formula (la) wherein R1 is methyl; R2 is cyano; • jy' - *»· R3 is hydrogen; X and Y are each oxygen; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. X; TABLE A6
Table A6 provides 352 compounds of formula (la) wherein R1 is ethyl; R2 is hydrogen; R3 is hydrogen; X and Y are each oxygen; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE A7
Table A7 provides 352 compounds of formula (la) wherein R1 is ethyl; R2 is fluoro; R3 is hydrogen; X and Y are each oxygen; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE A8
Table A8 provides 352 compounds of formula (la) wherein R’ is ethyl; R2 is chloro; R3 is hydrogen; X and Y are each oxygen; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE A9
Table A9 provides 352 compounds of formula (la) wherein R1 is ethyl; R: is bromo; R3 is hydrogen; X and Y are each oxygen; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE A10
Table A10 provides 352 compounds of formula (la) wherein R1 is ethyl; R2 is cyano; R3 is hydrogen; X and Y are each oxygen; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE All
Table Al 1 provides 352 compounds of formula (la) wherein R1 is methyl; R2 is hydrogen; R3 is hydrogen; X is oxygen; Y is sulphur; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE A12
Table A12 provides 352 compounds of formula (la) wherein R1 is methyl; R2 is fluoro; R3 is hydrogen; X is oxygen; Y is sulphur; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE A13
Table A13 provides 352 compounds of formula (la) wherein R1 is methyl; R2 is chloro; R3 is hydrogen; X is oxygen; Y is sulphur; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE A14
Table A14 provides 352 compounds of formula (la) wherein R1 is methyl; R2 is bromo; R3 is hydrogen; X is oxygen; Y is sulphur; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE A15
Table A15 provides 352 compounds of formula (la) wherein R1 is methyl; R2 is cyano; R3 is hydrogen; X is oxygen; Y is sulphur; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE A16
Table Al 6 provides 352 compounds of formula (la) wherein R1 is ethyl; R2 is hydrogen; R3 is hydrogen; X is oxygen; Y is sulphur; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE A17
Table A17 provides 352 compounds of formula (la) wherein R1 is ethyl; R2 is fluoro; R3 is hydrogen; X is oxygen; Y is sulphur; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE A18
Table Al 8 provides 352 compounds of formula (la) wherein R1 is ethyl; R2 is chloro; R3 is hydrogen; X is oxygen; Y is sulphur; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table A1. TABLE A19
Table A19 provides 352 compounds of formula (la) wherein R1 is ethyl; R2 is bromo; . R3 is hydrogen; X is oxygen; Y is sulphur; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE A20
Table A20 provides 352 compounds of formula (Ia) wherein R1 is ethyl; R2 is cyano; R3 is hydrogen; X is oxygen; Y is sulphur; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE A21
Table A21 provides 352 compounds of formula (lb) wherein R1 is methyl; R2 is hydrogen; R3 is hydrogen; X and Y are each oxygen; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE A22
Table A22 provides 352 compounds of formula (lb) wherein R1 is methyl; R2 is fluoro; R3 is hydrogen; X and Y are each oxygen; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE A23
Table A23 provides 352 compounds of formula (lb) wherein R' is methyl; R2 is chloro; R3 is hydrogen; X and Y are each oxygen; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE A24
Table A24 provides 352 compounds of formula (lb) wherein R1 is methyl; R: is bromo; R3 is hydrogen; X and Y are each oxygen; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE A25
Table A25 provides 352 compounds of formula (lb) wherein Rl is methyl; R2 is cyano; R3 is hydrogen; X and Y are each oxygen; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE A26
Table A26 provides 352 compounds of formula (lb) wherein R1 is ethyl; R2 is hydrogen; R3 is hydrogen; X and Y are each oxygen; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE A27
Table A27 provides 352 compounds of formula (lb) wherein R1 is ethyl; R2 is fluoro; R3 is hydrogen; X and Y are each oxygen; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE A28
Table A28 provides 352 compounds of formula (lb) wherein R1 is ethyl; R2 is chloro; R3 is hydrogen; X and Y are each oxygen; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE A29
Table A29 provides 352 compounds of formula (lb) wherein R1 is ethyl; R2 is bromo; R3 is hydrogen; X and Y are each oxygen; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE A30
Table A30 provides 352 compounds of formula (lb) wherein R1 is ethyl; R2 is cyano; R3 is hydrogen; X and Y are each oxygen; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE A31
Table A31 provides 352 compounds of formula (lb) wherein R1 is methyl; R2 is hydrogen; R3 is hydrogen; X is oxygen; Y is sulphur; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE A32
Table A32 provides 352 compounds of formula (lb) wherein R1 is methyl; R2 is fluoro; R3 is hydrogen; X is oxygen; Y is sulphur; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE A33
Table A33 provides 352 compounds of formula (lb) wherein R1 is methyl; R2 is chloro; R3 is hydrogen; X is oxygen; Y is sulphur; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE A34
Table A34 provides 352 compounds of formula (lb) wherein R1 is methyl; R2 is bromo; R3 is hydrogen; X is oxygen; Y is sulphur; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE A35
Table A35 provides 352 compounds of formula (lb) wherein R1 is methyl; R2 is cyano; R3 is hydrogen; X is oxygen; Y is sulphur; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE A36
Table A36 provides 352 compounds of formula (lb) wherein R1 is ethyl; R2 is hydrogen; R3 is hydrogen; X is oxygen; Y is sulphur; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE A37
Table A3 7 provides 352 compounds of formula (lb) wherein R1 is ethyl; R2 is fluoro; R3 is hydrogen; X is oxygen; Y is sulphur; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table A1. TABLE A38
Table A38 provides 352 compounds of formula (lb) wherein R1 is ethyl; R2 is chloro; R3 is hydrogen; X is oxygen; Y is sulphur; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE A3 9
Table A39 provides 352 compounds of formula (lb) wherein R’ is ethyl; R: is bromo; R3 is hydrogen; X is oxygen; Y is sulphur; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE A40
Table A40 provides 352 compounds of formula (lb) wherein R1 is ethyl; R2 is cyano; R3 is hydrogen; X is oxygen; Y is sulphur; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE A41
Table A41 provides 352 compounds of formula (lb) wherein R1 is methyl; R2 is hydrogen; R3 is hydrogen; X is oxygen; Y is NR7; R7 is hydrogen; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE A42
Table A42 provides 352 compounds of formula (lb) wherein R1 is methyl; R2 is fluoro; R3 is hydrogen; X is oxygen; Y is NR7; R7 is hydrogen; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE A43
Table A43 provides 352 compounds of formula (lb) wherein R1 is methyl; R2 is chloro; R3 is hydrogen; X is oxygen; Y is NR7; R7 is hydrogen; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE A44
Table A44 provides 352 compounds of formula (lb) wherein R1 is methyl; R2 is bromo; R3 is hydrogen; X is oxygen; Y is NR7; R7 is hydrogen; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE A45
Table A45 provides 352 compounds of formula (lb) wherein R1 is methyl; R2 is cyano; R3 is hydrogen; X is oxygen; Y is NR7; R7 is hydrogen; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE A46
Table A46 provides 352 compounds of formula (lb) wherein R1 is ethyl; R2 is hydrogen; R3 is hydrogen; X is oxygen; Y is NR7; R7 is hydrogen; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE A47
Table A47 provides 352 compounds of formula (lb) wherein R1 is ethyl; R2 is fluoro; R3 is hydrogen; X is oxygen; Y is NR7; R7 is hydrogen; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE A48
Table A48 provides 352 compounds of formula (lb) wherein R1 is ethyl; R2 is chloro; R3 is hydrogen; X is oxygen; Y is NR7; R7 is hydrogen; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE A49
Table A49 provides 352 compounds of formula (lb) wherein R1 is ethyl; R2 is bromo; R3 is hydrogen; X is oxygen; Y is NR7; R7 is hydrogen; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al.
TABLE A5Q
Table A50 provides 352 compounds of formula (lb) wherein R1 is ethyl; R2 is cyano; R3 is hydrogen; X is oxygen; Y is NR7; R7 is hydrogen; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE A51
Table A51 provides 352 compounds of formula (lb) wherein R1 is methyl; R2 is hydrogen; R3 is hydrogen; X is oxygen; Y is NR7; R7 is methyl; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE A52
Table A52 provides 352 compounds of formula (lb) wherein R1 is methyl; R2 is fluoro; R3 is hydrogen; X is oxygen; Y is NR7; R7 is methyl; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE A53
Table A53 provides 352 compounds of formula (lb) wherein R1 is methyl; R2 is chloro; R3 is hydrogen; X is oxygen; Y is NR7; R7 is methyl; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE A54
Table A54 provides 352 compounds of formula (lb) wherein R* is methyl; R2 is bromo; R3 is hydrogen; X is oxygen; Y is NR7; R7 is methyl; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE A55
Table A55 provides 352 compounds of formula (lb) wherein R1 is methyl; R2 is cyano; R3 is hydrogen; X is oxygen; Y is NR7; R7 is methyl; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE A56
Table A56 provides 352 compounds of formula (lb) wherein R1 is ethyl; R2 is hydrogen; R3 is hydrogen; X is oxygen; Y is NR7; R7 is methyl; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE A57
Table A57 provides 352 compounds of formula (lb) wherein R' is ethyl; R2 is fluoro; R3 is hydrogen; X is oxygen; Y is NR7; R7 is methyl; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE A58
Table A58 provides 352 compounds of formula (lb) wherenrRHs ethyl; R2is chl'oro; R3 is hydrogen; X is oxygen; Y is NR7; R7 is methyl; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE A59
Table A59 provides 352 compounds of formula (lb) wherein R1 is ethyl; R2 is bromo; R3 is hydrogen; X is oxygen; Y is NR7; R7 is methyl; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE A60
Table A60 provides 352 compounds of formula (lb) whereinR1 is ethyl; R2 is cyano; R3 is hydrogen; X is oxygen; Y is NR7; R7 is methyl; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE A61
Table A61 provides 352 compounds of formula (la) wherein R1 is methyl; R: is hydrogen; R3 is hydrogen; X is oxygen; Y is NR7; R7 is methyl; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE A62
Table A62 provides 352 compounds of formula (la) wherein R' is methyl; R2 is fluoro; R3 is hydrogen; X is oxygen; Y is NR7; R7 is methyl; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE A63
Table A63 provides 352 compounds of formula (la) wherein R1 is methyl; R2 is chloro; R3 is hydrogen; X is oxygen; Y is NR7; R7 is methyl; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE A64
Table A 64 provides 352 compounds of formula (la) wherein R1 is methyl; R2 is bromo; R3 is hydrogen; X is oxygen; Y is NR7; R7 is methyl; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE A65
Table A65 provides 352 compounds of formula (lb) wherein R1 is methyl; R2 is cyano; R3 is hydrogen; X is oxygen; Y is NR7; R7 is methyl; n is 0; and the values of R4 match those of the comespondingly numbered compounds of Table Al. TABLE A66
Table A66 provides 352 compounds of formula (la) wherein R1 is ethyl; R2 is hydrogen; R3 is hydrogen; X is oxygen; Y is NR7; R7 is methyl; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE A67
Table A67 provides 352 compounds of formula (la) wherein Rl is ethyl; R2 is fluoro; R3 is hydrogen; X is oxygen; Y is NR7; R7 is methyl; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE A68
Table A68 provides 352 compounds of formula (la) wherein R1 is ethyl; R2 is chloro; R3 is hydrogen; X is oxygen; Y is NR7; R7 is methyl; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE A69
Table A69 provides 352 compounds of formula (la) wherein R1 is ethyl; R2 is bromo; R3 is hydrogen; X is oxygen; Y is NR7; R7 is methyl; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE A70
Table A70 provides 352 compounds of formula (la) wherein R' is ethyl; R2 is cyano; R3 is hydrogen; X is oxygen; Y is NR7; R7 is methyl; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al.
TABLE BI
Table BI provides 352 compounds of formula (la) wherein R1 is methyl; R2 is hydrogen; R3 is methyl; X and Y are each oxygen; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE B2
Table B2 provides 352 compounds of formula (la) wherein R1 is methyl; R2 is fluoro; R3 is methyl; X and Y are each oxygen; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table A1. TABLE B3
Table B3 provides 352 compounds of formula (la) wherein R1 is methyl; R2 is chloro; R3 is methyl; X and Y are each oxygen; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE B4
Table B4 provides 352 compounds of formula (la) wherein R1 is methyl; R2 is bromo; R3 is methyl; X and Y are each oxygen; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE B5
Table B5 provides 352 compounds of formula (la) wherein R1 is methyl; R2 is cyano; R3 is methyl; X and Y are each oxygen; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE B6
Table B6 provides 352 compounds of formula (la) wherein R1 is ethyl; R2 is hydrogen; R3 is methyl; X and Y are each oxygen; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE B7
Table B7 provides 352 compounds of formula (la) wherein R1 is ethyl; R2 is fluoro; R3 is methyl; X and Y are each oxygen; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE B8
Table B8 provides 352 compounds of formula (la) wherein R1 is ethyl; R2 is chloro; R3 is methyl; X and Y are each oxygen; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE B9
Table B9 provides 352 compounds of formula (la) wherein R' is ethyl; R2 is bromo; R3 is methyl; X and Y are each oxygen; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al.
TABLE BIO
Table BIO provides 352 compounds of formula (la) wherein R1 is ethyl; R2 is cyano; R3 is methyl; X and Y are each oxygen; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE Bll
Table Bll provides 352 compounds of formula (la) wherein R1 is methyl; R2 is hydrogen; R3 is methyl; X is oxygen; Y is sulphur; n is 0; and the values of R4 match those oi the correspondingly numbered compounds of Table A1. TABLE B12
Table B12 provides 352 compounds of formula (la) wherein R1 is methyl; R2 is fluoro; R3 is methyl; X is oxygen; Y is sulphur; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE B13
Table BI 3 provides 352 compounds of formula (la) wherein R1 is methyl; R2 is chloro; RJ is methyl; X is oxygen; Y is sulphur; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE BI 4
Table B14 provides 352 compounds of formula (la) wherein R1 is methyl; R2 is bromo; R3 is methyl; X is oxygen; Y is sulphur; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE B15
Table B15 provides 352 compounds of formula (la) wherein R1 is methyl; R2 is cyano; R3 is methyl; X is oxygen; Y is sulphur; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE BI6
Table BI 6 provides 352 compounds of formula (la) wherein R1 is ethyl; R2 is hydrogen; R3 is methyl; X is oxygen; Y is sulphur; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE B17
Table B17 provides 352 compounds of formula (la) wherein R1 is ethyl; R2 is fluoro; R3 is methyl; X is oxygen; Y is sulphur; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE B18
Table B18 provides 352 compounds of formula (la) wherein R1 is ethyl; R2 is chloro; R3 is methyl; X is oxygen; Y is sulphur; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE B19
Table BI 9 provides 352 compounds of formula (la) wherein R1 is ethyl; R2 is bromo; R3 is methyl; X is oxygen; Y is sulphur; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE B20
Table B20 provides 352 compounds of formula (la) wherein R1 is ethyl; R2 is cyano; R3 is methyl; X is oxygen; Y is sulphur; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE B21
Table B21 provides 352 compounds of formula (lb) wherein R1 is methyl; R2 is hydrogen; R3 is methyl; X and Y are each oxygen; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE B22
Table B22 provides 352 compounds of formula (lb) wherein R1 is methyl; R2 is fluoro; R3 is methyl; X and Y are each oxygen; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE B23
Table B23 provides 352 compounds of formula (lb) wherein R1 is methyl; R2 is chloro; R3 is methyl; X and Y are each oxygen; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE B24
Table B24 provides 352 compounds of formula (lb) wherein R1 is methyl; R2 is bromo; R3 is methyl; X and Y are each oxygen; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE B25
Table B25 provides 352 compounds of formula (lb) wherein R1 is methyl; R2 is cyano; R3 is methyl; X and Y are each oxygen; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table A1. TABLE B26
Table B26 provides 352 compounds of formula (lb) wherein R1 is ethyl; R2 is hydrogen; R3 is methyl; X and Y are each oxygen; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al. TABLE B27
Table B27 provides 352 compounds of formula (lb) wherein R1 is ethyl; R2 is fluoro; R3 is methyl; X and Y are each oxygen; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table A1. TABLE B28
Table B28 provides 352 compounds of formula (lb) wherein Rl is ethyl; R2 is chloro; R3 is methyl; X and Y are each oxygen; n is 0; and the values of R4 match those of the correspondingly numbered compounds of Table Al.
Claims (1)
- Original document published without claims.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9816654.9A GB9816654D0 (en) | 1998-07-30 | 1998-07-30 | Chemical compounds |
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| Publication Number | Publication Date |
|---|---|
| AP9901616A0 AP9901616A0 (en) | 1999-09-30 |
| AP969A true AP969A (en) | 2001-05-29 |
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| Application Number | Title | Priority Date | Filing Date |
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| APAP/P/1999/001616A AP969A (en) | 1998-07-30 | 1999-07-29 | Benzazoles: benxoxazole, benzthiazole and benzimidazole derivatives. |
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| EP (1) | EP1100798B1 (en) |
| JP (1) | JP4545933B2 (en) |
| KR (1) | KR100558630B1 (en) |
| CN (1) | CN1196699C (en) |
| AP (1) | AP969A (en) |
| AR (1) | AR019486A1 (en) |
| AT (1) | ATE224390T1 (en) |
| AU (1) | AU755291B2 (en) |
| BR (1) | BR9912616A (en) |
| CA (1) | CA2338048C (en) |
| CO (1) | CO5190721A1 (en) |
| DE (1) | DE69903044T2 (en) |
| DK (1) | DK1100798T3 (en) |
| EG (1) | EG22178A (en) |
| ES (1) | ES2184482T3 (en) |
| GB (1) | GB9816654D0 (en) |
| GT (1) | GT199900119A (en) |
| HK (1) | HK1040714A1 (en) |
| HN (1) | HN1999000127A (en) |
| HU (1) | HUP0103695A3 (en) |
| IL (2) | IL141109A0 (en) |
| MY (1) | MY133385A (en) |
| NZ (1) | NZ509431A (en) |
| PE (1) | PE20001005A1 (en) |
| PT (1) | PT1100798E (en) |
| SV (1) | SV1999000119A (en) |
| TW (1) | TW522151B (en) |
| WO (1) | WO2000006566A1 (en) |
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| GB0002029D0 (en) * | 2000-01-28 | 2000-03-22 | Zeneca Ltd | Chemical compounds |
| GB0002040D0 (en) * | 2000-01-28 | 2000-03-22 | Zeneca Ltd | Chemical compounds |
| PE20010830A1 (en) | 2000-01-28 | 2001-09-06 | Syngenta Ltd | DERIVATIVES OF AZOL INSECTICIDES OR FUNGICIDES AND COMPOSITIONS THAT INCLUDE THEM |
| GB0002033D0 (en) * | 2000-01-28 | 2000-03-22 | Zeneca Ltd | Chemical compounds |
| GB0002036D0 (en) * | 2000-01-28 | 2000-03-22 | Zeneca Ltd | Chemical compounds |
| GB0002031D0 (en) * | 2000-01-28 | 2000-03-22 | Zeneca Ltd | Chemical compounds |
| GB0012806D0 (en) * | 2000-05-25 | 2000-07-19 | Zeneca Ltd | Chemical compounds |
| US6448281B1 (en) | 2000-07-06 | 2002-09-10 | Boehringer Ingelheim (Canada) Ltd. | Viral polymerase inhibitors |
| GB0102109D0 (en) * | 2001-01-26 | 2001-03-14 | Syngenta Ltd | Chemical process |
| GB0102110D0 (en) * | 2001-01-26 | 2001-03-14 | Syngenta Ltd | Chemical process |
| GB0118357D0 (en) * | 2001-07-27 | 2001-09-19 | Syngenta Ltd | Chemical compounds |
| ES2524803T3 (en) * | 2002-12-19 | 2014-12-12 | The Scripps Research Institute | Compositions and methods to stabilize transthyretin and inhibit the abnormal folding of transthyretin |
| CN102911161A (en) | 2004-02-20 | 2013-02-06 | 贝林格尔.英格海姆国际有限公司 | Viral polymerase inhibitors |
| US20050261365A1 (en) | 2004-05-20 | 2005-11-24 | The Scripps Research Institute | Transthyretin stabilization |
| WO2005115148A1 (en) * | 2004-05-24 | 2005-12-08 | Cropsolution, Inc. | 3-aryl-3-hydroxy-2-methylenepropionic acid esters as fungicides |
| WO2006023899A1 (en) * | 2004-08-24 | 2006-03-02 | Bayer Cropscience Lp | Method of fungal pathogen control in grass or turf |
| DE102004049761A1 (en) * | 2004-10-12 | 2006-04-13 | Bayer Cropscience Ag | Fungicidal drug combinations |
| US7662824B2 (en) | 2005-03-18 | 2010-02-16 | Janssen Pharmaceutica Nv | Acylhydrazones as kinase modulators |
| GB0517051D0 (en) * | 2005-08-19 | 2005-09-28 | Syngenta Ltd | Chemical process |
| CN101374843B (en) | 2005-12-21 | 2012-09-05 | 詹森药业有限公司 | Triazolopyridazines as tyrosine kinase modulators |
| EP2074223A4 (en) * | 2006-09-15 | 2010-03-10 | Foldrx Pharmaceuticals Inc | Assays for detecting native-state proteins and identifying compounds that modulate the stability of native-state proteins |
| JP5369854B2 (en) * | 2008-04-21 | 2013-12-18 | 住友化学株式会社 | Harmful arthropod control composition and condensed heterocyclic compound |
| US20090318393A1 (en) * | 2008-06-23 | 2009-12-24 | Shalaby Shalaby W | Film-forming liquid formulations for controlled release of pesticides |
| US20120245159A1 (en) * | 2009-09-30 | 2012-09-27 | Sumitomo Chemical Company, Limited | Composition and method for controlling arthropod pests |
| JP5540640B2 (en) * | 2009-10-07 | 2014-07-02 | 住友化学株式会社 | Heterocyclic compounds and their use for controlling harmful arthropods |
| TW201117724A (en) * | 2009-10-20 | 2011-06-01 | Sumitomo Chemical Co | Composition and method for controlling arthropod pests |
| AR079009A1 (en) * | 2009-10-20 | 2011-12-21 | Sumitomo Chemical Co | COMPOSITION AND METHOD TO CONTROL PESTS OF ARTROPODES |
| EP2490539A4 (en) * | 2009-10-20 | 2013-04-24 | Sumitomo Chemical Co | Composition and method for controlling arthropod pests |
| BR112012009259A2 (en) * | 2009-10-20 | 2019-09-24 | Sumitomo Chemical Co | composition and method for controlling arthropod pests. |
| BR112013016022B1 (en) * | 2010-12-24 | 2019-05-07 | Sumitomo Chemical Company, Limited | Fused heterocyclic compound and use for same control. |
| SG2014013270A (en) | 2011-09-16 | 2014-05-29 | Pfizer | Solid forms of a transthyretin dissociation inhibitor |
| CN103193770B (en) * | 2013-03-20 | 2015-10-28 | 中国人民解放军第二军医大学 | Replace benzothiazoles antifungal compound and preparation method thereof and application |
| CN104292180A (en) * | 2014-10-12 | 2015-01-21 | 湖南华腾制药有限公司 | Preparation method of oxadiazole derivative |
| WO2017178819A1 (en) * | 2016-04-13 | 2017-10-19 | Redag Crop Protection Ltd | Agricultural chemicals |
| CN109867666B (en) * | 2017-12-02 | 2021-09-07 | 沈阳中化农药化工研发有限公司 | Aromatic acetamide compound containing isothiazole ring and application thereof |
| JP7344493B2 (en) * | 2019-04-15 | 2023-09-14 | 国立研究開発法人物質・材料研究機構 | Pest control agent, pest control method, and pest control agent kit |
| WO2022178694A1 (en) * | 2021-02-23 | 2022-09-01 | 苏州大学 | Method for preparing alkylbenzothiazole derivative under visible light |
| CN112979580B (en) * | 2021-02-23 | 2022-02-25 | 苏州大学 | Method for preparing alkyl benzothiazole derivative under visible light |
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| EP0640597A1 (en) * | 1993-08-24 | 1995-03-01 | BASF Aktiengesellschaft | Acylamino substituted isoxazoles and/or isothiazols, process for their preparation and their use |
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| EP0640597A1 (en) * | 1993-08-24 | 1995-03-01 | BASF Aktiengesellschaft | Acylamino substituted isoxazoles and/or isothiazols, process for their preparation and their use |
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