KR927003569A - Pyrimidine derivatives, methods for their preparation, pharmaceuticals containing grills and their use as fungicides - Google Patents

Pyrimidine derivatives, methods for their preparation, pharmaceuticals containing grills and their use as fungicides Download PDF

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KR927003569A
KR927003569A KR1019920701086A KR920701086A KR927003569A KR 927003569 A KR927003569 A KR 927003569A KR 1019920701086 A KR1019920701086 A KR 1019920701086A KR 920701086 A KR920701086 A KR 920701086A KR 927003569 A KR927003569 A KR 927003569A
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alkyl
alkoxy
phenyl
alkylthio
halogen
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긴케 볼프강
자흐제 부르크하르트
빅케 하인리히
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쿠르트 오일러
훽스트 아크티엔게젤샤프트
프란쯔 라피체
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines

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  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
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  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

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피리미딘 유도체, 그의 제조방법, 그를 함유하는 약제 및 살진균제로서 그의 용도Pyrimidine derivatives, methods for their preparation, pharmaceuticals containing them and their use as fungicides

[도면의 간단한 설명][Brief Description of Drawings]

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음Since this is an open matter, no full text was included.

Claims (6)

하기 일반식(I)의 화합물 및 그의 산 부가염:Compounds of the general formula (I) and acid addition salts thereof 상기 식에서, R1은 수소, (C1-C6)알킬, (C1-C4)알콕시-(C1-C4)알킬, (C1-C4)알킬티오-(C1-C4)알킬, (C2-C6)알케닐, (C2-C6)알키닐, (C3-C7)사이클로알킬, (C3-C7)사이클로알킬(C1-C4)알킬(이때, 상기 사이클로알킬 잔기는 (C1-C4)알킬에 의해서 일치환 내지 삼치환될 수 있다), 또는 페닐, 페녹시-(C1-C4)알킬, 페닐머캅토(C1-C4)알킬, 페닐-(C1-C4)알킬 또는 페녹시-페녹시(C1-C4)알일(이때, 상기 페닐 잔기는 할로겐, 니트로, (C1-C4)알킬, (C1-C4)알콕시 (C1-C4)알킬티오, (C1-C4)할로알킬 또는 (C1-C4)할로알콕시에 의해 일치환 내지 삼치환될 수 있다)이고, R2, R3및 R4는 서로 독립적으로 수소, (C1-C6)알킬 또는 페닐(이때, 상기 페닐 라디칼은 할로겐, 니트로, (C1-C4)알킬, (C1-C4)알콕시, (C1-C4)알킬티오, (C1-C4)할로알킬 또는 (C1-C4)할로알콕시에 의해 일치환 내지 삼치환 될 수 있다)이며, R5는 수소, (C1-C6)알킬, (C3-C7)사이클로알킬, (C3-C7)사이클로알킬-(C1-C4)알킬(이때, 상기 사이클로알킬잔기는 (C1-C4)알킬에 의해 일치환 내지 삼치환될 수 있다), (C1-C4)할로알킬, (C1-C4)알콕시, (C1-C4)알킬티오, (C1-C4)알콕시-(C1-C4)알킬, (C1-C4)알킬티오-(C1-C4)알킬, 할로겐, (C2-C6)알케닐, (C2-C6)알키닐, 페닐, 페녹시, 페닐(C1-C4)알킬, 페녹시-(C1-C4)알킬, 페닐머캅토-(C1-C4)알킬, 페닐머캅토, 페닐-(C1-C4)알콕시 또는 페닐-(C1-C4)알킬티오(이때, 페닐 잔기는 할로겐, 니트로, 시아노, (C1-C4)알킬, (C1-C4)알콕시, (C1-C4)알킬티오, (C1-C4)할로알킬 또는 (C1-C4)할로알콕시에 의해 일치환 내지 삼치환 될 수 있다), 또는 (C2-C4)알케닐록시, (C2-C4)알키닐록시, (C1-C4)할로알콕시, (C1-C4)알콕시-(C1-C4)알콕시 또는 (C1-C4)알킬티오-(C1-C4)알킬티오이고, R6는 수소, (C1-C4)알킬, (C1-C4)알콕시, (C2-C6)알케닐록시, (C2-C6)알키닐록시, (C1-C4)알킬티오, 할로겐 또는 페닐(이때, 상기 페닐 라디칼은 할로겐, 니트로, 시아노, (C1-C4)알킬, (C1-C4)알콕시, (C1-C4)알킬티오, (C1-C4)할로알킬 또는 (C1-C4)할로알콕시에 의해 일치환 내지 삼치환 될 수 있다)이며, R7, R8, R9및 R10은 서로 독립적으로 수소, 할로겐, 니트로, 시아노, (C1-C4)알킬, (C1-C4)알콕시, (C1-C4)알킬티오, (C1-C4)할로알킬 또는 (C1-C4)할로알콕시이고, R11및 R12는 서로 독립적으로 수소 또는 (C1-C4)알킬이며, n은 1내지 3이다.Wherein R 1 is hydrogen, (C 1 -C 6 ) alkyl, (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylthio- (C 1 -C 4 ) alkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (C 3 -C 7 ) cycloalkyl, (C 3 -C 7 ) cycloalkyl (C 1 -C 4 ) Alkyl wherein said cycloalkyl moiety may be mono- to trisubstituted by (C 1 -C 4 ) alkyl, or phenyl, phenoxy- (C 1 -C 4 ) alkyl, phenylmercapto (C 1 -C 4 ) alkyl, phenyl- (C 1 -C 4 ) alkyl or phenoxy-phenoxy (C 1 -C 4 ) alyl, wherein the phenyl moiety is halogen, nitro, (C 1 -C 4 ) alkyl, Mono- or tri-substituted by (C 1 -C 4 ) alkoxy (C 1 -C 4 ) alkylthio, (C 1 -C 4 ) haloalkyl or (C 1 -C 4 ) haloalkoxy), R 2 , R 3 and R 4 independently of one another are hydrogen, (C 1 -C 6 ) alkyl or phenyl wherein the phenyl radical is halogen, nitro, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) Alkoxy, (C 1 -C 4 ) alkylthio, (C 1 -C 4 ) haloalkyl or (C 1 -C 4), and one can be substituted to three) by a haloalkoxy, R 5 is hydrogen, (C 1 -C 6) alkyl, (C 3 -C 7) cycloalkyl, (C 3 -C 7 ) Cycloalkyl- (C 1 -C 4 ) alkyl wherein the cycloalkyl moiety may be mono- to trisubstituted by (C 1 -C 4 ) alkyl, (C 1 -C 4 ) haloalkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylthio, (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylthio- (C 1 -C 4 ) alkyl, halogen, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, phenyl, phenoxy, phenyl (C 1 -C 4 ) alkyl, phenoxy- (C 1- C 4 ) alkyl, phenylmercapto- (C 1 -C 4 ) alkyl, phenylmercapto, phenyl- (C 1 -C 4 ) alkoxy or phenyl- (C 1 -C 4 ) alkylthio, wherein the phenyl moiety is Halogen, nitro, cyano, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylthio, (C 1 -C 4 ) haloalkyl or (C 1 -C 4) by a haloalkoxy group may be substituted to three days), or (C 2 -C 4) alkenyl, hydroxy, (C2-C4) alkynyl Hydroxy, (C 1 -C 4) haloalkoxy, (C 1 -C 4) alkoxy - (C 1 -C 4) alkoxy or (C 1 -C 4) alkylthio - (C 1 -C 4) alkylthio, and , R 6 is hydrogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, (C 2 -C 6 ) alkenyloxy, (C 2 -C 6 ) alkynyloxy, (C 1- C 4 ) alkylthio, halogen or phenyl, wherein the phenyl radical is halogen, nitro, cyano, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylthio , (C 1 -C 4 ) haloalkyl or (C 1 -C 4 ) haloalkoxy may be mono- to tri-substituted), and R 7 , R 8 , R 9 and R 10 are each independently hydrogen, Halogen, nitro, cyano, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylthio, (C 1 -C 4 ) haloalkyl or (C 1 -C 4 ) haloalkoxy, R 11 and R 12 independently of one another are hydrogen or (C 1 -C 4 ) alkyl, n is 1 to 3. 제1항에 있어서, R1이 수소, (C1-C6)알킬, 페닐, 페닐-(C1-C2)알킬, 페녹시-페녹시-(C1-C2)알킬 또는 페녹시(C1-C2)알킬(이때, 상기 페닐 잔기는 할로겐 또는 (C1-C4)알킬에 의해서 일치환 내지 삼치환될 수 있다) 또는 (C1-C3)알콕시-(C1-C2)알킬이고, R2및 R3가 서로 독립적으로 수소, (C1-C3)알킬 또는 페닐(이때, 상기 페닐 라디칼은 할로겐 또는 (C1-C4)알킬에 의해서 일치환 내지 삼치환될 수 있다)이며, R4가 수소이고, R5가 수소, (C1-C6)알킬, (C3-C6)사이클로알킬, (C5-C6)사이클로알킬-(C1-C3)알킬, 페닐, 페닐-(C1-C2)알킬티오, 페닐-(C1-C2)알킬(이때, 상기 페닐 잔기는 할로겐 또는 (C1-C4)알킬, (C1-C3)할로 알킬 또는 (C1-C4)알콕시에 의해서 일치환 내지 삼치환될 수 있다) 또는 (C1-C4)알콕시, (C1-C4)알킬티오, (C2-C4)알케닐록시, (C2-C4)알키닐록시, (C2-C3)알케닐, (C2-C4)알키닐, 또는 (C1-C4)알콕시-(C1-C4)알콕시이며, R6가 수소, (C1-C4)알킬, 할로겐, 페닐 또는 (C1-C3)알콕시이고, R7, R8, R9및 R10은 서로 독립적으로 수소, (C1-C4)알킬, (C1-C4)할로알킬 또는 (C1-C4)알킬티오이며, R11및 R12가 수소이고, n이 1인 화합물 및 그의 산 부가염,The compound of claim 1, wherein R 1 is hydrogen, (C 1 -C 6 ) alkyl, phenyl, phenyl- (C 1 -C 2 ) alkyl, phenoxy-phenoxy- (C 1 -C 2 ) alkyl or phenoxy (C 1 -C 2 ) alkyl wherein the phenyl moiety may be mono- to trisubstituted by halogen or (C 1 -C 4 ) alkyl or (C 1 -C 3 ) alkoxy- (C 1- C 2 ) alkyl, and R 2 and R 3 are independently of each other hydrogen, (C 1 -C 3 ) alkyl or phenyl, wherein the phenyl radical is mono- or tricyclic with halogen or (C 1 -C 4 ) alkyl May be substituted), R 4 is hydrogen, R 5 is hydrogen, (C 1 -C 6 ) alkyl, (C 3 -C 6 ) cycloalkyl, (C 5 -C 6 ) cycloalkyl- (C 1 -C 3 ) alkyl, phenyl, phenyl- (C 1 -C 2 ) alkylthio, phenyl- (C 1 -C 2 ) alkyl, wherein the phenyl moiety is halogen or (C 1 -C 4 ) alkyl, (C Mono- to trisubstituted by 1- C 3 ) halo alkyl or (C 1 -C 4 ) alkoxy) or (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylthio, (C 2 -C 4) alkenyl Hydroxy, (C 2 -C 4) alkynyl, hydroxy, (C 2 -C 3) alkenyl, (C 2 -C 4) alkynyl, or (C 1 -C 4) alkoxy - (C 1 -C 4) Alkoxy, R 6 is hydrogen, (C 1 -C 4 ) alkyl, halogen, phenyl or (C 1 -C 3 ) alkoxy, and R 7 , R 8 , R 9 and R 10 are each independently hydrogen, (C 1- C 4 ) alkyl, (C 1 -C 4 ) haloalkyl or (C 1 -C 4 ) alkylthio, R 11 and R 12 are hydrogen, n is 1 and acid addition salts thereof, a) R5가 H인 화합물을 제조하려는 경우, R5가 할로겐이고 나머지 모든 치환체들이 제1항에서 정의한 바와 같은 일반식(I)의 적합한 할로피리미딘을 환원적으로 탈할로겐화시키거나, 또는 b) R5가 (C1-C4)알콕시, (C1-C4)알킬티오, 페녹시, 페니머캅토, 페닐-(C1-C4)알콕시 또는 페닐-(C1-C4)알킬티오(이때, 상기 페닐 잔기는 할로겐, 니트로, 시아노, (C1-C4)알킬, (C1-C4)알콕시, (C1-C4)알킬티오, (C1-C4)할로알킬 또는 (C1-C4)할로알콕시에 의해 일치환 내지 삼치환 될 수 있다) 또는 (C2-C4)알케닐록시, (C2-C4)알키닐록시, (C1-C4)할로알콕시, (C1-C4)알콕시-(C1-C4)알콕시 또는 (C1-C4)알킬티오-(C1-C4)알킬티오인 일반식(I)의 화합물을 제조하려는 경우, R5가 할로겐인 일반식(I)의 적합한 할로피리미딘과 일반식 R5-Y(II)(여기에서, R5는 상기 정의한 바와 같고, Y는 알칼리금속이다)의 알칼리 금속 화합물을 반응시키거나, 또는 c) R5가 (C1-C6)알킬, (C3-C7)사이클로알킬, (C3-C7)사이클로알킬-(C1-C4)알킬, (C1-C4)알콕시-(C1-C4)알킬, (C1-C4)알킬티오-(C1-C4)알킬 또는 페닐(이때 상기 페닐 라디칼은 (C1-C4)알킬 또는 (C1-C4)알콕시에 의해 일치환 내지 삼치환될 수 있다)인 일반식(I)의 화합물을 제조하려는 경우, 니켈-포스핀 착화합물의 존재하에서, R5가 할로겐인 일반식( I)의 적합한 할로피리미딘과 그리나드 화합물 R5MgX(III)(여기에서, R5는 상기 정의 한 바와 같고, X는 할로겐이다)을 반응시킴을 포함하는 제1항 또는 제2항에 청구된 일반식(I) 화합물의 제조방법.a) when preparing a compound in which R 5 is H, reductively dehalogenating a suitable halopyrimidine of general formula (I) as defined in claim 1, wherein R 5 is halogen and all remaining substituents are defined in claim 1, or b ) R 5 is (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylthio, phenoxy, phenamercapto, phenyl- (C 1 -C 4 ) alkoxy or phenyl- (C 1 -C 4 ) Alkylthio wherein the phenyl moiety is halogen, nitro, cyano, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylthio, (C 1 -C 4 Mono- or tri-substituted by haloalkyl or (C 1 -C 4 ) haloalkoxy) or (C 2 -C 4 ) alkenyloxy, (C 2 -C 4 ) alkynyloxy, (C 1 -C 4) haloalkoxy, (C 1 -C 4) alkoxy-in general formula (I) (C 1 -C 4 ) alkylthio - (C 1 -C 4) alkoxy or (C 1 -C 4) alkylthio If the compound to manufacture, R 5 is halogen in formula (I) the general formula R 5 -Y (II) with the appropriate halo-pyrimidine of (wherein, R 5 is Reacting the alkali metal compound of the group is as defined, Y is an alkali metal), or c) R 5 is (C 1 -C 6) alkyl, (C 3 -C 7) cycloalkyl, (C 3 -C 7 ) cycloalkyl- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylthio- (C 1 -C 4 ) alkyl Or phenyl, wherein the phenyl radical is mono- to trisubstituted by (C 1 -C 4 ) alkyl or (C 1 -C 4 ) alkoxy to prepare a compound of formula (I) - in the presence of a phosphine complex, R 5 is in the Grignard compound R 5 MgX (III) (here with a suitable halo-pyrimidine of the halogen in the formula (I), R 5 is as above defined, X is a halogen A process for preparing the compound of formula (I) as claimed in claim 1 or 2, comprising reacting. 유효량의 제1항 또는 제2항에 청구된 일반식(I)화합물을 함유하는 살진균제.A fungicide containing an effective amount of the compound of formula (I) as claimed in claim 1. 유해 진균을 박멸하기 위한 제1항 또는 제2항에 청구된 일반식(I)화합물의 용도.Use of a compound of formula (I) as claimed in claim 1 or 2 to combat harmful fungi. 유효량의 제1항 또는 제2항에 청구된 일반식(I)의 화합물을 유해 진균에 의해 침습된 식물 표면 또는 기질에 적용함을 포함하는 상기 유해 진균의 박멸 방법.A method for eradicating harmful fungi comprising applying an effective amount of a compound of formula (I) as claimed in claim 1 to a plant surface or substrate invaded by harmful fungi. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR1019920701086A 1989-11-09 1990-11-07 Pyrimidine derivatives, methods for their preparation, pharmaceuticals containing grills and their use as fungicides KR927003569A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE3937284A DE3937284A1 (en) 1989-11-09 1989-11-09 PYRIMIDINE DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF, THE AGENTS CONTAINING THEY AND THEIR USE AS FUNGICIDES
DEP3937284.7 1989-11-09
PCT/EP1990/001858 WO1991007400A1 (en) 1989-11-09 1990-11-07 Pyrimidine derivatives, process for making them, agents containing them and their use as fungicides

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KR927003569A true KR927003569A (en) 1992-12-18

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JP (1) JPH05501550A (en)
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AU (1) AU6638990A (en)
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CA (1) CA2068328A1 (en)
DE (1) DE3937284A1 (en)
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IL (1) IL96271A0 (en)
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GB9024873D0 (en) * 1990-11-15 1991-01-02 Ici Plc Fungicidal compounds
WO1992010490A1 (en) * 1990-12-05 1992-06-25 Hoechst Aktiengesellschaft Pyridyl-pyrimidin-derivates, process for producing the same, agents containing the same and their use as fungicides
DE4105751A1 (en) * 1991-02-23 1992-08-27 Bayer Ag SUBSTITUTED PYRIDYLPYRIMIDINE, THEIR PRODUCTION AND THEIR USE AND NEW INTERMEDIATE PRODUCTS
WO1993014080A1 (en) * 1992-01-15 1993-07-22 E.I. Du Pont De Nemours And Company Bridged heterocyclic fungicides
EP1373222A2 (en) 2001-03-15 2004-01-02 Basf Aktiengesellschaft 5-phenylpyrimidine, methods and intermediate products for the production thereof and use of the same for controlling pathogenic fungi
CN100357297C (en) * 2003-02-06 2007-12-26 巴斯福股份公司 Pyrimidines, methods for the production thereof, and use thereof

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DE3675197D1 (en) * 1985-12-03 1990-11-29 Sumitomo Chemical Co PYRIDINYLPYRIMIDINE DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THESE PLANT DISEASES PROTECTIVE CONTAINING THE ACTIVE SUBSTANCE.
CA1288433C (en) * 1986-12-03 1991-09-03 Tsuguhiro Katoh Pyridinylpyrimidine derivatives, method for production thereof and a fungicide containing them as the active ingredient

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CN1051559A (en) 1991-05-22
AU6638990A (en) 1991-06-13
BR9007833A (en) 1992-09-22
EP0518862A1 (en) 1992-12-23
WO1991007400A1 (en) 1991-05-30
HUT62287A (en) 1993-04-28
JPH05501550A (en) 1993-03-25
YU212990A (en) 1992-09-07
DE3937284A1 (en) 1991-05-16
ZA908958B (en) 1991-08-28
HU9201543D0 (en) 1992-09-28
CA2068328A1 (en) 1991-05-10
PT95831A (en) 1991-09-13
MX23260A (en) 1993-06-01

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