Preparation of dihydropyrrole derivatives 机翻标题: 暂无翻译,请尝试点击翻译按钮。

源语言标题
(JP2013529594) ジヒドロピロール​誘導体​の​調製​方法
公开号/公开日
JP2013529594 A 2013-07-22 [JP2013529594] / 2013-07-22
申请号/申请日
2013JP-0513716 / 2011-06-14
发明人
;
申请人
SYNGENTA;SYNGENTA PARTICIPATIONS;
主分类号
IPC分类号
A01N-043/36A01N-043/40A01P-007/02A01P-007/04C07B-053/00C07B-061/00C07C-205/54C07C-251/24C07C-255/23C07D-207/18C07D-207/22C07D-207/46C07D-401/06C07D-403/04C07D-405/04C07D-417/06
摘要
(JP2013529594) The present invention provides stereoselective processes for the preparation of compounds of formula (I) wherein P is phenyl, naphthyl, a 6-membered heteroaryl group containing one or two nitrogen atoms as ring members, or a 10-membered bicyclic heteroaryl group containing one or two nitrogen atoms as ring members, and wherein the phenyl, naphthyl and heteroaryl groups are optionally substituted; R1 is chlorodifluoromethyl or trifluoromethyl; R2 is optionally substituted aryl or optionally substituted heteroaryl; n is 0 or 1; including the process comprising (a-i) reacting a compound of formula II wherein P, R1 and R2 are as defined for the compound of formula I; with nitromethane in the presence a chiral catalyst to give a compound of formula III Wherein P, R1 and R2 are as defined for the compound of formula I; and (a-ii) reductively cyclizing the compound of formula III to give the compound of formula I.  The invention also provides intermediates useful for processes for the synthesis of compounds of formula (I).  (From US9233920 B2)
机翻摘要
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地址
代理人
代理机构
;
优先权号
2010EP-0196633 2010-12-22 2010WO-EP58207 2010-06-11 2011WO-EP59823 2011-06-14
主权利要求
(JP2013529594) 1. I compound of the formula  (xLxWx, P is, phenyl, naphthyl, 2 1 nitrogen atoms in the ring one or two 6 - membered heteroaryl groups containing a 1 - membered or as one or two nitrogen atoms in the ring 2 to 10 - membered bicyclic heteroaryl contains as a ring member and the base, wherein, said phenyl, naphthyl and heteroaryl groups are optionally substituted and; R1 is chlorodifluoromethyl or trifluoromethyl and; R2 is by any means or any aryl is optionally substituted heteroaryl and optionally substituted by respectively; n is 1 or 0 is a) a method for preparation of, a compound of the formula II (a-i)  (xLxWx, P, R1 and R2 I for compounds of formulas are as defined) in the presence of a chiral catalyst to nitromethane of formula III is reacted with the compound  (xLxWx, P, R1 and R2 I compounds of formulas are as defined for) the step of obtaining, of the formula III (a-ii) and a compound of the formula I cyclized by reducing a compound of the steps of obtaining an; (b-i) or a compound of the formula II  (xLxWx, P, R1 and R2 I is a compound of the formula are as defined for a given) of a cyanide source in the presence of a chiral catalyst and a compound of the formula IV  (˜C, P, R1 and R2 I is a compound of the formula are as defined for) the step of obtaining, (b-ii) and a compound of the formula IV where n is 0 the reducing cyclization I Eqs step to provide a compound of; or a compound of the formula (c-i) II  (xLxWx, P, R1 and R2 I compounds of formulas are as defined for) the compound of the formula XXII  (xLxWx, W may be a hydrogen or optionally substituted aryl, optionally substituted by aryl Y and, and, which is optionally substituted Z alkyl or optionally substituted aryl is a) a chiral catalyst and in the presence of a compound of the formula XXIII reacting  (xLxWx, P, R1 and R2 is defined for a compound of formula I spectrumcomprises and, as well as, Y, wherein the compound of formula XXII W Z and defined as follows for) (c-ii) to obtain a compound of formula XXIII with a suitable base or suitable acid treated -W (=O) grycans Y-C with, a compound of formula XXIV  (˜C, P, R1 and R2 is defined for the compound of formula I spectrumcomprises and, as well as, XXII as defined for the compounds of the formula Z spectrumcomprises in a) the step of obtaining, and (c-iii) wherein said compound is XXIV n is 0 to decarboxylation to obtain said compounds I; or (d-i) a compound of the formula XXV  (xLxWx, R1 and R2 space is defined for a compound of the formula I spectrumcomprises in) with a compound of the formula XXVI  (xLxWx, as defined for a compound of the formula P I spectrumcomprises in) a chiral catalyst and in the presence of the compound of formula III is reacted with the  (xLxWx, P, R1 and R2 I compounds of formulas are as defined for) the step of obtaining, (d-ii) and a compound of the formula III is cyclized by reduction of a compound of formula comprising the step I.  2. I is a compound of the formula, (b) (a) a method in accordance with the method or the preparation, method according to claim 1.  3. In which the catalyst is chiral, Chiral cinchona alkaloid derivative, urea derivative Kiraruchio, chiral urea derivatives, Kiraruaza - crown ether derivative, a chiral metal complex, or a guanidine derivative Kiraruamijin, Chiral pyrrolidine or imidazolidine derivative, Chiral scandium III complexes, Kirarunafuchiru phase transfer catalyst, the catalyst (galodinium) or strontium Chiral Gallo pyridinium, Chiral crown ether derivative, or, is an alkaline earth metal with respect to the chiral, or a method according to claim 2 claim 1.  4. Wherein the chiral catalyst is Chiral cinchona alkaloid or a derivative thereof, according to the method of any one of claims 1-3.  5. I is a compound of the formula is prepared by a method with, the Chiral cinchona alkaloid derivative, the compound of formula VII  (˜C, W1 is ethyl or vinyl; R30 is hydrogen or C1 -C4 alkoxy; R31 is, hydroxyl, C1 -C4 alkoxy, C2 -C4 alkenyloxy or benzyloxy optionally is substituted; R32 is optionally substituted aryl or optionally substituted heteroaryl and; X anion that is a) a compound of the formula IX or  (xLxWx, Y O and S is or, W3 is ethyl or vinyl; R37 is hydrogen or C1 -C4 alkoxy; R38 is optionally substituted aryl or optionally substituted C3 -C10 cycloalkyl) or a compound of the formula X  (xLxWx, W4 is ethyl or vinyl; R54 is hydrogen or C1 -C4 alkoxy; R55 is optionally substituted with aryl) in which, method according to claim 4.  6. Claim Chiral cinchona alkaloid derivative is a compound of formula IX, method according to claim 5.  7. I is a compound of the formula (b) is prepared by a method with, a compound of the formula VII wherein Chiral cinchona alkaloid derivative  (˜C, W1 is ethyl or vinyl; R30 is hydrogen or C1 -C4 alkoxy; R31 is, hydroxyl, C1 -C4 alkoxy, C2 -C4 alkenyloxy or benzyloxy optionally is substituted; R32 is optionally substituted aryl or optionally substituted heteroaryl; X is an anion) is, method according to claim 4.  8. I is a compound of the formula (c) and is prepared by a method, wherein the compound of formula VII Chiral cinchona alkaloid derivative  (xLxWx, W1 is ethyl or vinyl; R30 is hydrogen or C1 -C4 alkoxy; R31 is C2 -C4 alkenyloxy or benzyloxy optionally is substituted; R32 is optionally substituted aryl or optionally substituted heteroaryl and; X is an anion) is, method according to claim 4.  9. A compound of the formula Ir  (xLxWx, P is, phenyl, naphthyl, 2 1 nitrogen atoms in the ring one or two 6 - membered heteroaryl groups containing a 1 - membered or as one or two nitrogen atoms in the ring as a ring member containing 2 to 10 - membered bicyclic heteroaryl group, wherein, said phenyl, naphthyl and heteroaryl groups are optionally substituted and; R1 is chlorodifluoromethyl or trifluoromethyl and; R2 is optionally substituted aryl or optionally substituted heteroaryl; n is 1 or 0 is a) a method for the preparation of; compound of the formula II (cr-i)  (xLxWx, P, R1 and R2 space is defined for a compound of the formula I spectrumcomprises in) with a compound of the formula XXII  (xLxWx, W is hydrogen or optionally substituted aryl and, aryl optionally substituted by any Y and, and, alkyl substituted Z is by any means or any alkylene is substituted by a) reacting a compound of formula XXIIIr with  (xLxWx, P, R1 and R2 is defined for a compound of formula I spectrumcomprises and, as well as, Y, wherein the compound of the formula XXII W Z and are are as defined for) (cr-ii) the step of obtaining the compound of formula XXIIIr with a suitable base or suitable acid treated -W (=O) Y-C releases, a compound of the formula XXIVr  (˜C, P, R1 and R2 is defined for a compound of the formula I spectrumcomprises and, as well as, XXII Z compounds of the formula are as defined for) the steps of obtaining an, wherein the compound XXIVr (cr-iii) and the n is 0 to decarboxylation to obtain said preparation method comprises the step I compound.  10. A compound of the formula Ir  (xLxWx, P is, phenyl, naphthyl, 1 - membered heterocycle containing one or two nitrogen atoms as the 2 6 - membered heteroaryl groups containing 1 or 2 - membered heterocycle containing one or two nitrogen atoms as ring member containing 10 - membered bicyclic heteroaryl group, wherein, said phenyl, naphthyl and heteroaryl groups are optionally substituted and; R1 is chlorodifluoromethyl or trifluoromethyl and; R2 is by any means or any aryl is optionally substituted heteroaryl and optionally substituted by respectively; n is 1 or 0 is a) a method for the preparation of, a compound of the formula XXV (dr-i)  (xLxWx, R1 and R2 I for compounds of formulas are as defined) compounds of the formula XXVI  (xLxWx, wherein the compound of the formula P I are as defined for) the compound of the formula III is reacted with r  (xLxWx, P, R1 and R2 I compounds of formulas are as defined for) the step of obtaining, and (dr-ii) reduction of compounds of Formula IIIr Formula cyclization I preparation to provide a compound of the step. 11. R2 is, -5 1 aryl or one of the two R3 aryl substituted, or, two 1 or two -5 heteroaryl R3 are heteroaryl substituted; each R3 is, independently, halogen, cyano, nitro, C1 -C8 alkyl, C1 -C8 haloalkyl, C2 -C8 alkenyl, C2 -C8 haloalkenyl, C2 -C8 alkynyl, C2 -C8 haloalkynyl, hydroxy, C1 -C8 alkylamino, C1 -C8 alkoxy, C1 -C8 haloalkoxy, mercapto, C1 -C8 alkylthio, C1 -C8 haloalkthio, C1 -C8 alkylsulfinyl, C1 -C8 haloalkylsulfinyl, C1 -C8 Examptes, C1 -C8 haloalkylsulfonyl, C1 -C8 alkylcarbonyl, C1 -C8 alkoxycarbonyl, -5 1 aryl or one of the two R4 aryl substituted, or, two 1 or two -5 heterocyclyl R4 is heterocyclyl substituted at; P is P2 or P1 in which  A1 、A2 、A3 、A4 is, independently of one another, C FixedDocument_add H, C-R5 is nitrogen or, if, A1 、A2 、A3 、A4 2 of nitrogen or less; a1' 、A2' 、A3' 、A4' 、A5' and A6' is, independently of one another, C FixedDocument_add H, C-R5 is nitrogen, however, A1' 、A2' 、A3' 、A4' 、A5' and A6' and 2 or less of nitrogen; each R5 is, independently, halogen, cyano, nitro, C1 -C8 alkyl, C1 -C8 haloalkyl, C2 -C8 alkenyl, C2 -C8 haloalkenyl, C2 -C8 alkynyl, C2 -C8 haloalkynyl, C3 -C10 cycloalkyl, C1 -C8 alkoxy, C1 -C8 haloalkoxy, C1 -C8 alkylthio, C1 -C8 haloalkthio, C1 -C8 alkylsulfinyl, C1 -C8 haloalkylsulfinyl, C1 -C8 Examptes or C1 -C8 haloalkylsulfonyl and; q is, hydrogen, halogen, nitro, NH2 、cyano, C1 -C8 alkyl, C1 -C8 haloalkyl, C2 -C8 alkenyl, C2 -C8 haloalkenyl, C2 -C8 alkynyl, C3 -C8 haloalkynyl, C3 -C10 cycloalkyl, C1 -C8 alkylthio, C1 -C8 haloalkthio, C1 -C8 alkylsulfinyl, C1 -C8 haloalkylsulfinyl, C1 -C8 Examptes, C1 -C8 haloalkylsulfonyl, arylsulfonyl or C1 -C4 tau.atxo alkyl and -5 1 are independently selected from a group substituted by one to three Aryjsulfonyl, -N (R6) R7b 、-C(=W5) N(R6) R7 、-C(R15) (R16) N(R17) R18 、-C(=W5) OR7a 、-C(=W5) R13 、-OR14 、-5 1 aryl or one of the two Z1 substituted with aryl, heterocyclyl or one or two 1 -5 Z1 is heterocyclyl which is substituted; R6 is, hydrogen, C1 -C8 alkyl, C1 -C8 alkoxy, C2 -C8 alkenyl, C2 -C8 alkynyl, C3 -C10 cycloalkyl, C3 -C10 cycloalkyl -C1 -C4 alkylene, C1 -C8 alkylcarbonyl or C1 -C8 ofPreferred and; r7 is, hydrogen, -5 1 alkyl or one of the two R8 substituted alkyl, alkenyl or 1 -5 of one of the two R8 alkenyl being substituted, -5 1 alkynyl or one of the two R8 alkynyl being substituted, C3 -C10 -5 1 cycloalkyl or one of the two R9 is substituted C3 -C10 cycloalkyl, C3 -C10 cycloalkyl -C1 -C4 alkylene or -5 1 cycloalkyl portion is of one R9 is substituted C3 -C10 cycloalkyl -C1 -C4 alkylene, C1 -C8 -N alkyl (R6) -C(=O) -C1 -C4 alkylene, C1 -C8 -N haloalkyl (R6) -C(=O) -C1 -C4 alkylene, C3 -C8 - cycloalkyl aminocarbonyl -C1 -C4 alkylene, C1 -C6 alkyl -O- N=CH -, C1 -C6 -O- N=CH - haloalkyl, aryl -C1 -C6 -5 1 alkylene or the aryl moiety is of one of the two R10 is substituted at the aryl -C1 -C6 alkylene, heterocyclyl -C1 -C6 alkylene or -5 1 heterocyclyl moiety of one of the two R10 substituted with heterocyclyl moiety, O, N, C=O, C=N - OR12 、N-R12 、S、SO、SO2 、S=N-R12 and SO=N -R12 are independently selected from a 1 - membered ring containing one or more of heterocyclyl -C1 -C6 alkylene; -5 1 aryl or one of the two R10 substituted with aryl, heterocyclyl or one or two 1 -5 R10 substituted with heterocyclyl moiety, O, N, C=O, C=N - OR12 、N-R12 、S、SO、SO2 、S=N-R12 and SO=N -R12 1 are independently selected from the groups containing one or more of the ring members is heterocyclyl; R7a is, hydrogen, -5 1 alkyl or one of the two R8 substituted alkyl, alkenyl or 1 -5 of one of the two R8 substituted in the alkenyl, 1 alkynyl or the two -5 one R8 alkynyl are optionally substituted, cycloalkyl of 1 or -5 one R9 substituted cycloalkyl, aryl alkylene or - 1 -5 of one of the aryl moieties may also be one R10 is substituted at the aryl - alkylene, - 1 alkylene or -5 heteroaryl heteroaryl moieties of the two R10 - heteroaryl optionally substituted alkylene, -5 1 aryl or one of the two R10 aryl substituted, or, two 1 or two -5 heteroaryl R10 is substituted and heteroaryl optionally substituted by; r7b is, hydrogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, Halo alkynyl cycloalkyl, halocycloalkyl, alkylcarbonyl, Haloalkylcarbonyl, alkoxycarbonyl, benzyl or Haloalkoxycarbonyl; each R8 is, independently, halogen, cyano, nitro, hydroxy, NH2 、mercapto, C1 -C8 alkyl, C1 -C8 haloalkyl, C1 -C8 alkoxy, C1 -C8 haloalkoxy, C1 -C8 alkylthio, C1 -C8 haloalkthio, C1 -C8 alkylsulfinyl, C1 -C8 haloalkylsulfinyl, C1 -C8 Examptes, C1 -C8 haloalkylsulfonyl, C1 -C8 alkylamino, C2 -C8 dialkylamino, C3 -C8 cycloalkylamino, C1 -C8 alkylcarbonyl, C1 -C8 alkoxycarbonyl, C1 -C8 alkylaminocarbonyl, C1 -C8 dialkylaminocarbonyl, C1 -C8 Haloalkylcarbonyl, C1 -C8 Haloalkoxycarbonyl, C1 -C8 Halo alkyl amino carbonyl, C1 -C8 Halo dialkylaminocarbonyl and; each R9 is, independently, halogen or C1 -C8 alkyl and; each R10 is, independently, halogen, cyano, nitro, C1 -C8 alkyl, C1 -C8 haloalkyl, C2 -C8 alkenyl, C2 -C8 haloalkenyl, C2 -C8 alkynyl, C2 -C8 haloalkynyl, hydroxy, C1 -C8 alkoxy, C1 -C8 haloalkoxy, mercapto, C1 -C8 alkylthio, C1 -C8 haloalkthio, C1 -C8 alkylsulfinyl, C1 -C8 haloalkylsulfinyl, C1 -C8 Examptes, C1 -C8 haloalkylsulfonyl, C1 -C8 alkylcarbonyl, C1 -C8 alkoxycarbonyl, -5 1 aryl or one of the two R11 aryl substituted, or, one or two 1 -5 heterocyclyl R11 is heterocyclyl which is substituted; each R4 and R11 is, independently, halogen, cyano, nitro, C1 -C8 alkyl, C1 -C8 haloalkyl, C1 -C8 alkoxy, C1 -C8 haloalkoxy or C1 -C8 ofPreferred and; each R12 is, independently, hydrogen, cyano, cyano -C1 -C8 alkyl, C1 -C8 alkyl, C1 -C8 haloalkyl, C3 -C8 cycloalkyl, 1 carbon atoms O, S, S (O) or SO2 substituted by C3 -C8 cycloalkyl, or, C3 -C8 Cycloalkjd -C1 -C8 alkylene, one carbon atom in the cycloalkyl group of 1 O, S, S (O) or SO2 substituted by C3 -C8 Cycloalkjd -C1 -C8 alkylene, or, C3 -C8 Cycloalkjd -C1 -C8 haloalkylene, C1 -C8 hydroxyalkyl, C1 -C8 alkOXy C1 -C8 alkylene, C2 -C8 alkenyl, C2 -C8 haloalkenyl, C2 -C8 alkynyl, C2 -C8 haloalkynyl, -3 1 aryl or one of the two R11 aryl substituted, C1 -C8 alkylcarbonyl, C1 -C8 Haloalkylcarbonyl, C1 -C8 alkoxycarbonyl, C1 -C8 Haloalkoxycarbonyl, C1 -C8 alkyl - sulfonyl, C1 -C8 haloalkylsulfonyl, aryl -C1 -C4 -3 1 alkylene or the aryl moiety is of one of the two R11 is substituted at the aryl -C1 -C4 alkylene, or, heteroaryl -C1 -C4 -3 1 alkylene or heteroaryl moieties of the two R11 and heteroaryl optionally substituted with -C1 -C4 alkylene, or, C1 -C4 (C1 -C4 -O- N=alkyl) C- CH - alkyl2 -and; R13 halogen or imidazole; each R14 is, independently, hydrogen, C1 -C8 alkyl, C2 -C8 alkenyl, C2 -C8 alkynyl, C3 -C10 Cycloalkjd, C1 -C6 alkyl -C3 -C8 Cycloalkjd, C3 -C8 Cycloalkjd -C1 -C6 alkylene, C1 -C10 alkylcarbonyl, C1 -C8 alkoxycarbonyl, C1 -C8 Examptes, C1 -C8 haloalkylsulfonyl, or, or a Aryjsulfonyl C1 -C4 tau.atxo alkyl and are independently selected independently from a -5 1 group substituted with one to two Aryjsulfonyl and; each R15 and R16 is, independently, hydrogen, C1 -C12 -5 1 alkyl or one of the two R8 is substituted C1 -C12 alkyl, C3 -C8 -5 1 cycloalkyl or one of the two R9 is substituted C3 -C8 cycloalkyl, C2 -C12 -5 1 alkenyl or one of the two R8 is substituted C2 -C12 alkenyl, C2 -C12 -5 1 alkynyl or one of the two R8 is substituted C2 -C12 alkynyl, cyano, C1 -C12 -5 1 alkoxycarbonyl or one of the two R8 is substituted C1 -C12 alkoxycarbonyl, C1 -C12 -5 1 or one of the two Alkoxythiocarbonyl R8 is substituted C1 -C12 Alkoxythiocarbonyl or, or, R15 and R16 is, together with the carbon atoms to which they are attached to, form a 3-6 membered carbocyclic ring which may be the; R17 is, hydrogen, NH2 、Silclean, C1 -C12 -5 1 alkoxy or one of the two R8 is substituted C1 -C12 alkOXy, C1 -C12 -5 alkylcarbonylamino or 1 alkyl of one R8 is substituted C1 -C12 alkylcarbonylamino, C1 -C12 -5 one alkyl or one of 1 substituents R8 is substituted C1 -C12 alkylamino, C1 -C12 -5 1 alkyl or one of the two R8 is substituted C1 -C12 alkyl, C3 -C8 -5 1 cycloalkyl or one of the two R9 is substituted C3 -C8 cycloalkyl, cyano, C2 -C12 -5 1 alkenyl or one of the two R8 is substituted C2 -C12 alkenyl, C2 -C12 -5 1 alkynyl or one of the two R8 is substituted C2 -C12 alkynyl, C1 -C12 -5 1 alkylcarbonyl or one of the two R8 is substituted C1 -C12 alkylcarbonyl, C1 -C12 -5 1 alkoxycarbonyl or one of the two R8 is substituted C1 -C12 ofPreferred or, or, CH2 -R19 、C(=O) R19 and (=S) C R19 selected from; r18 is, hydrogen, cyano, carbonyl, thiocarbonyl, C1 -C12 -5 1 alkylcarbonyl or one of the two R8 is substituted C1 -C12 alkylcarbonyl, C1 -C12 -5 1 or one of the two Alkyl thiocarbonyl R8 is substituted C1 -C12 Alkyl thiocarbonyl, C1 -C12 -5 one alkyl or one of 1 alkylaminocarbonyl R8 is substituted C1 -C12 alkylaminocarbonyl, C1 -C12 -5 one alkyl or one of 1 R8 is substituted C1 -C12 , C2 -C24 (having a total carbon number) dialkylaminocarbonyl wherein the alkyl is 1 -5 or one or both of or one of the two R8 is substituted C2 -C24 (having a total carbon number) dialkylaminocarbonyl, C2 -C24 (total number of carbon atoms) alkyl of one Dialkylaminothiocarbonyl -5 1 or one or both of the two R8 is substituted C2 -C24 (having a total carbon number) Dialkylaminothiocarbonyl, C1 -C12 Alkoxyamino carbonyl -5 1 alkoxy or one of the two R8 is substituted C1 -C12 Alkoxyamino carbonyl, C1 -C12 -5 1 alkoxy or one of the two Alkoxyamino thiocarbonyl R8 is substituted C1 -C12 Alkoxyamino thiocarbonyl, C1 -C12 -5 1 alkoxycarbonyl or one of the two R8 is substituted C1 -C12 ofPreferred, C1 -C12 -5 1 or one of the two Alkoxythiocarbonyl R8 is substituted C1 -C12 Alkoxythiocarbonyl, C1 -C12 -5 1 or one of the two R8 is substituted C1 -C12 , C1 -C12 -5 1 or one of the two Thio alkoxythiocarbonyl R8 is substituted C1 -C12 Thio alkoxythiocarbonyl, C1 -C12 Examptes -5 1 or one of the two R8 is substituted C1 -C12 Examptes, C3 -C12 cycloalkylcarbonyk -5 1 or one of the two R9 is substituted C3 -C12 cycloalkylcarbonyk, C2 -C12 -5 one of 1 or alkenylcarbonyl R8 is substituted C2 -C12 alkenylcarbonyl, C2 -C12 -5 1 or one of the two Alkynylcarbonyl R8 is substituted C2 -C12 Alkynylcarbonyl, C3 -C12 cycloalkyl -C1 -C12 -5 1 alkylcarbonyl or one of the two R9 is substituted C3 -C12 cycloalkyl -C1 -C12 alkylcarbonyl, C1 -C12 Alkylsulfenyl -C1 -C12 -5 1 alkylcarbonyl or one of the two R8 is substituted C1 -C12 Alkylsulfenyl -C1 -C12 alkylcarbonyl, C1 -C12 alkylsulfinyl -C1 -C12 -5 1 alkylcarbonyl or one of the two R8 is substituted C1 -C12 alkylsulfinyl -C1 -C12 alkylcarbonyl, C1 -C12 Examptes -C1 -C12 -5 1 alkylcarbonyl or one of the two R8 is substituted C1 -C12 Examptes -C1 -C12 alkylcarbonyl, C1 -C12 alkylcarbonyl -C1 -C12 -5 1 alkylcarbonyl or one of the two R8 is substituted C1 -C12 alkylcarbonyl -C1 -C12 alkylcarbonyl, C3 -C12 -5 1 cycloalkyl or one of the two cycloalkylaminocarbonyl R9 is substituted C3 -C12 cycloalkylaminocarbonyl, C2 -C12 Alkenylamino carbonyl -5 1 alkenyl or one of the two R8 is substituted C2 -C12 Alkenylamino carbonyl, C2 -C12 Alkynylcarbonyl Roh carbonyl -5 1 alkynyl or one of the two R8 is substituted C2 -C12 Alkynylcarbonyl Roh carbonyl or, or, (=O) C R19 (=S) C and R19 selected from; or, R17 and R18 is, together with the nitrogen atom to which they are attached to, one or two 1 -5 R11 may be substituted, or, a keto, thioketo or nitroimino group substituted by a 3-6 - membered heterocyclic ring may form a; R19 is, -5 1 aryl or one of the two R11 substituted with aryl, heterocyclyl or one or two 1 -5 R11 is heterocyclyl substituted at; Aryjsulfonyl or each C1 -C4 tau.atxo alkyl and -5 1 are independently selected from one of the one group substituted with arylsulfonyl, independently, halogen, C1 -C12 -5 1 alkyl or one of the two R8 is substituted C1 -C12 alkyl, nitro, C1 -C12 -5 1 alkoxy or one of the two R8 is substituted C1 -C12 alkOXy, cyano, C1 -C12 alkylsulfinyl, C1 -C12 Examptes, C1 -C12 haloalkylsulfinyl, C1 -C12 haloalkylsulfonyl, hydroxyl or thiol group and; each W5 is, independently, is a O S or, according to any one of claims 1-10 method.   12. R2 is, -5 1 or a phenyl or one of the two R3 and substituted phenyl; Q where, cyano, halogen, nitro, NH2 、Aryjsulfonyl or C1 -C4 tau.atxo alkyl and -5 1 are independently selected from a group substituted by one to three Aryjsulfonyl, -5 one of 1 or heterocyclyl Z1 heterocyclyl are substituted with, - OR14 、-C(=O) N(R6) R7 、-C(=O) OR7a 、-C(=O) R13 or -C (R15) (R16) N(R17) R18 in, method according to claim 11.  13. P is P3 and;  A3 and A4 FPAs C-H is, or, A3 and A4 and so as to be one of the other C-H Nitrogen; R5a hydrogen; R5b methyl; or, R5a and R5b together form a bridge - CH=CH-CH=CH -; Q where, cyano, halogen, nitro, NH2 、or phenylsulfonylacetate C1 -C4 tau.atxo alkyl and -5 1 are independently selected from one of the two substituted phenylsulfonyl group, - OR14 、-C(=O) N(R6) R7 、-C(=O) OR7a 、-C(=O) R13 、-C(R15) (R16) N(R17) R18 or the heterocyclic ring is selected from H1 - H9;  kis 0, 1 or 2 and; R6 is, hydrogen, C1 -C8 alkyl, C1 -C8 alkoxy, C1 -C8 alkylcarbonyl or C1 -C8 ofPreferred and; r7 is, hydrogen, C1 -C8 -5 1 alkyl or one of the two R8 is substituted C1 -C8 alkyl, C3 -C10 -5 1 cycloalkyl or one of the two R9 is substituted C3 -C10 cycloalkyl, aryl -C1 -C6 -5 1 alkylene or the aryl moiety is of one of the two R10 is substituted at the aryl -C1 -C6 alkylene, heterocyclyl -C1 -C6 alkylene or -5 1 heterocyclyl moiety of one of the two R10 heterocyclyl are substituted with -C1 -C6 alkylene (each heterocyclyl moiety O, N, C=O, C=N FixedDocument_add OR12 、N-R12 、S、SO、SO2 、S=N-R12 and SO=N FixedDocument_add R12 independently selected 1 to one or more ring members are a containing), -5 1 aryl or one of the two R10 substituted aryl, one or two 1 -5 heterocyclyl R10 substituted in the heterocyclyl (each heterocyclyl moiety O, N, C=O, C=N FixedDocument_add OR12 、N-R12 、S、SO、SO2 、S=N-R12 and SO=N FixedDocument_add R12 independently selected 1 one or more rings containing Otis), C1 -C8 -N alkyl (R6) -C(=O) -C1 -C4 alkylene, C1 -C8 -N haloalkyl (R6) -C(=O) -C1 -C4 alkylene, C3 -C8 - cycloalkyl aminocarbonyl -C1 -C4 alkylene, C1 -C6 alkyl -O FixedDocument_add N=CH -, C1 -C6 haloalkyl is -O FixedDocument_add N=CH -; R7a is, C1 -C15 alkyl, C1 -C15 haloalkyl, C2 -C15 alkenyl, C2 -C15 haloalkenyl, pyridyl or benzyl and, or a method according to claim 12 claim 11.  14. Q is, cyano, halogen, nitro, NH2 、C1 -C8 alkoxy, phenylsulfonyl or C1 -C4 tau.atxo alkyl and -5 1 are independently selected from a group substituted by one to three phenylsulfonylacetate, (=O) N - C (R6) R7 、-C(=O) OR7a 、-C(=O) R13 、-C(R15) (R16) N(R17) R18 or heterocyclic and is selected from H1 - H9; R6 is, hydrogen, C1 -C8 alkyl, C1 -C8 alkOXy, C1 -C8 alkylcarbonyl or C1 -C8 ofPreferred and; r7 is, hydrogen, C1 -C8 alkyl, C1 -C8 haloalkyl, phenyl -C1 -C6 -5 1 alkylene or phenyl moieties of the two R10 phenyl substituted -C1 -C6 alkylene, pyridyl -C1 -C6 -4 1 is alkylene or pyridyl moiety of one of the two R10 is pyridyl substituted with -C1 -C6 alkylene, thiazolyl -C1 -C6 2 1 alkylene or thiazolyl moiety is one or two of the two R10 thiazolyl substituted with -C1 -C6 alkylene, or a phenyl or 1 -5 of one of the two R10 is substituted by a phenyl, pyridyl or one of 1 -4 R10 pyridyl which is substituted, one or two 1 2 thiazolyl or R10 substituted thiazolyl are, C3 -C6 O or 1 cycloalkyl or one ring atom is a substituted S C3 -C6 cycloalkyl, C1 -C4 alkyl -O FixedDocument_add N=CH -, C1 -C4 -O FixedDocument_add N=CH - haloalkyl, C1 -C4 -N alkyl (R6) -C(=O) -CH2 -、C1 -C4 -N haloalkyl (R6) -C(=O) -CH2 -or a group of the formulA;  Lis a single bond or C1 -C6 alkylene; Y1 、Y2 and Y3 is, independently of one another, CR21 R22 、C=O、C=N-OR12 、N-R12 、S、SO、SO2 、S=N-R12 or SO=N FixedDocument_add R12 is, however, Y1 、Y2 or Y3 1 of at least one is CR21 R22 、C=OC=N-OR or12 but; each R8 is, independently, halogen, cyano, nitro, hydroxy, C1 -C8 alkoxy, C1 -C8 haloalkoxy, C1 -C8 alkylcarbonyl, C1 -C8 alkoxycarbonyl, mercapto, C1 -C8 alkylthio, C1 -C8 haloalkthio, C1 -C8 alkylsulfinyl, C1 -C8 haloalkylsulfinyl, C1 -C8 Examptes - and; each R12 is, independently, hydrogen, cyano, C1 -C8 alkyl, C1 -C8 haloalkyl, C1 -C8 alkylcarbonyl, C1 -C8 Haloalkylcarbonyl, C1 -C8 alkoxycarbonyl, C1 -C8 Haloalkoxycarbonyl, C1 -C8 Examptes, C1 -C8 haloalkylsulfonyl, aryl -C1 -C4 -3 1 alkylene or the aryl moiety is of one of the two R11 is substituted at the aryl -C1 -C4 alkylene or heteroaryl -C1 -C4 -3 1 alkylene or heteroaryl moieties of the two R11 and heteroaryl optionally substituted with -C1 -C4 alkylene; R15 and R16 is, hydrogen, halogen, cyano, C1 -C4 alkyl, C1 -C4 are independently selected from haloalkyl; R17 is, hydrogen, C1 -C8 alkyl, C1 -C8 alkoxy, C1 -C8 alkylcarbonyl, or C1 -C8 ofPreferred and; R18 is, C1 -C4 -5 1 alkylcarbonyl or one of the two R8 is substituted C1 -C4 alkylcarbonyl, C3 -C6 cycloalkylcarbonyk -5 1 cycloalkyl or one of the two R9 is substituted C3 -C6 cycloalkylcarbonyk and; R20 hydrogen or C1 -C8 alkyl; each R21 and R22 is, independently, hydrogen, halogen, C1 -C8 alkyl or C1 -C8 haloalkyl; each Z1 is, independently, halogen, cyano, C1 -C4 alkyl, C1 -C4 haloalkylinclude, C1 -C4 alkoxy, C1 -C4 haloalkoxy, according to the method of any one of claims 11-13.  15. Q is, -C N (=O) (R6) R7 、-C(R15) (R16) N(R17) R18 、or, heterocycle selected from H1 - H9, method according to claim 14.  16. Q is -C N (=O) (R6) R7 and, and, R7 (A) a radical of the formula, method according to claim 14.  17. I compound of the formula  (˜C, P, R1 、R2 and n is, in any one of claims 1-16 I compound of the formula are as defined for a given) or, a salt or oxide N -; or, a compound of the formula III  (˜C, P, R1 and R2 is, in any one of claims 1-16 I compound of the formula are as defined for a given) or, a salt or oxide N -; or, a compound of the formula IV  (xLxWx, P, R1 and R2 is, in the formula of any one of claims 1-16 I as defined for the compounds of a) or, a salt or oxide N -; or, a compound of the formula XXIII  (xLxWx, P, R1 and R2 is, in the formula of any one of claims 1-16 I as defined for a compound of and, wherein, which is substituted by any W being hydrogen or aryl, each of which is substituted by any Y and aryl groups, and, each of which is substituted by any Z any alkylene is optionally substituted by an alkyl or alkyl in a) or, a salt or oxide N -; or, a compound of the formula XXIV  (xLxWx, P, R1 and R2 is, according to any one of claims 1-16 I in defined for the compounds of the formula spectrumcomprises and, as well as, Z is, optionally substituted alkyl or optionally substituted with aryl) or, a salt or oxide N -.  18. I Eqn compound and a compound of formula IA  (xLxWx, R1 is trifluoromethyl or chlorodifluoromethyl is; R2 is optionally substituted aryl or optionally substituted heteroaryl; P is, phenyl, naphthyl, one of 1 2 containing one or two nitrogen atoms in the ring 1 or 6 - membered heteroaryl groups containing as a ring member with one or two nitrogen atoms in the ring as a ring member containing 2 to 10 - membered bicyclic heteroaryl group is, wherein, said phenyl, naphthyl and heteroaryl groups are optionally substituted and; n is 1 or 0 is a) a mixture comprising, a compound of the formula I said enriched mixture; or of the formula III and a compound of formula IIIA compound  (xLxWx, P, R1 and R2 space is defined for a compound of the formula I is spectrumcomprises) mixture comprising, wherein the compound of formula III is enriched in the said mixture; or formula IV and a compound of formula IVA compound  (xLxWx, R1 、R2 I P and compounds of the formulas are as defined for a given) or of a mixture comprising, a compound of the formula IV being enriched in the said mixture; or of the formula XXIII and a compound of formula XXIIIA compound  (xLxWx, R1 、R2 I P and compounds of the formulas can be as defined for a given, in this case, the optional Y is hydrogen or a substituted aryl, optionally substituted by aryl W and, and, substituted Z is by any means to an alkyl or alkyl optionally substituted with aryl) or of a mixture comprising, wherein the compound of the formula XXIII wherein the mixture is enriched in; and a compound of formula XXIV or formula compound XXIVA  (xLxWx, R1 、R2 P and defined for a compound of the formula I spectrumcomprises and, as well as, optionally substituted alkyl Z is optionally substituted on the aryl or in) a mixture comprising, a compound of the formula XXIV wherein the mixture is enriched.  19. V with a compound of the formula  (xLxWx, R1 、R2 、A3 、A4 、R5a 、R5b and n in the formula of any one of claims 1-16 is I as defined for a compound of which, as well as, R is halogen, OH or C1 -C15 alkoxy) or, a salt or oxide N -; or, a compound of the formula VI  (xLxWx, R1 、R2 、A3 、A4 、R5a 、R5b and n is, in the formula of any one of claims 1-16 I as defined for a compound of and, and, XB is a leaving group) or, a salt or oxide N -.  20. A compound of formula XXIIIr  (xLxWx, P, R1 and R2 is, in the formula of any one of claims 1-16 I as defined for a compound of and, in this case, W may be a hydrogen or optionally substituted aryl, optionally substituted by aryl Y and, and, substituted Z is by any means to an alkyl or alkyl optionally substituted with aryl) or, or a salt or oxide N -; or, a compound of the formula XXIVr  (˜C, P, R1 and R2 is, in any one of claims 1-16 I defined for a compound of the formula spectrumcomprises and, as well as, substituted Z is by any means to an alkyl or alkyl optionally substituted with aryl) or, or a salt or oxide N -.  21. I claim 15 or 16 defined in the formula for the preparation of compounds of the pest control method, according to any one of claims 1-16 in method step.  22. To a pest, a habitat of a pest, or to, a pest to a plant susceptible to attack by the, formula defined in claim 18 I enantiomers of the compounds of the mixture i(...)
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