CN1257904C - 用作杀真菌剂的5-卤代-6-苯基-7-氟烷基氨基三唑并嘧啶 - Google Patents
用作杀真菌剂的5-卤代-6-苯基-7-氟烷基氨基三唑并嘧啶 Download PDFInfo
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- CN1257904C CN1257904C CNB028080807A CN02808080A CN1257904C CN 1257904 C CN1257904 C CN 1257904C CN B028080807 A CNB028080807 A CN B028080807A CN 02808080 A CN02808080 A CN 02808080A CN 1257904 C CN1257904 C CN 1257904C
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- KNCYXPMJDCCGSJ-UHFFFAOYSA-N piperidine-2,6-dione Chemical compound O=C1CCCC(=O)N1 KNCYXPMJDCCGSJ-UHFFFAOYSA-N 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- HZRSNVGNWUDEFX-UHFFFAOYSA-N pyraclostrobin Chemical compound COC(=O)N(OC)C1=CC=CC=C1COC1=NN(C=2C=CC(Cl)=CC=2)C=C1 HZRSNVGNWUDEFX-UHFFFAOYSA-N 0.000 description 1
- ZLIBICFPKPWGIZ-UHFFFAOYSA-N pyrimethanil Chemical compound CC1=CC(C)=NC(NC=2C=CC=CC=2)=N1 ZLIBICFPKPWGIZ-UHFFFAOYSA-N 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 210000000582 semen Anatomy 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000014347 soups Nutrition 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- APEJMQOBVMLION-VOTSOKGWSA-N trans-cinnamamide Chemical compound NC(=O)\C=C\C1=CC=CC=C1 APEJMQOBVMLION-VOTSOKGWSA-N 0.000 description 1
- POFDSYGXHVPQNX-UHFFFAOYSA-N triazolo[1,5-a]pyrimidine Chemical compound C1=CC=NC2=CN=NN21 POFDSYGXHVPQNX-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 229940087291 tridecyl alcohol Drugs 0.000 description 1
- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
本发明涉及式(I)的5-卤代-6-苯基-7-氟烷基氨基三唑并嘧啶,其中R1为氢、氟、烷基、链烯基、炔基、链烷二烯基,其中这些基团的碳链可以未被取代或如说明书所定义的那样被取代;R2为氢、烷基、链烯基、炔基、链烷二烯基,其中这些基团可以是未取代的或取代的;R3为氟烷基或氟链烯基;X为卤素;n为0或1-4的整数;L各自独立地为卤素、硝基、烷基、卤代烷基、烷氧基或卤代烷氧基。本发明还涉及它们的制备、包含它们的组合物以及它们在防治植物病原性真菌中的用途。
Description
本发明涉及式I的5-卤代-6-苯基-7-氟烷基氨基三唑并嘧啶:
其中R1为氢、氟、C1-C10-烷基、C2-C10-链烯基、C2-C10-炔基、C2-C10-链烷二烯基,
其中这些基团的碳链可以未被取代或被部分或全部卤代或可以携带1-3个基团Ra,
Ra为氰基、硝基、羟基、C1-C6-烷基、C1-C6-卤代烷基、C1-C6-烷基羰基、C3-C6-环烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基、C1-C6-烷氧羰基、C1-C6-烷硫基、C1-C6-烷基氨基,
二-C1-C6-烷基氨基、C2-C6-链烯基、C2-C6-链烯氧基、C3-C6-炔氧基和C1-C4-亚烷二氧基,其可以被卤代;
R2为氢、C1-C10-烷基、C2-C10-链烯基、C2-C10-炔基、C2-C10-链烷二烯基,其中这些基团可以未被取代或被部分或全部卤代或可以携带1-3个基团Ra,
R3为C2-C8-氟烷基或C2-C8-氟链烯基;
X为卤素;
n为0或1-4的整数;
L各自独立地为卤素、硝基、C1-C10-烷基、C1-C6-卤代烷基、C1-C10-烷氧基或C1-C6-卤代烷氧基。
此外,本发明还涉及它们的制备方法、包含它们的组合物以及它们在防治植物病原性真菌中的用途。
EP-A 071 792公开了其中5位被氢或烷基或芳基取代的6-苯基-7-氨基三唑并嘧啶。
EP-A 550 113涉及其中7-氨基被进一步取代的5-H-和5-卤代-6-苯基-7-氨基三唑并嘧啶。
WO-A 98/46607公开了杀真菌的三唑并嘧啶,它们在6-位被2,4,6-三氟苯基取代。
WO-A 98/46608公开了杀真菌的三唑并嘧啶,它们在7-位被氟烷基氨基取代。
上述文献中所公开的化合物据说对各种植物病原性真菌具有活性。
本发明的目的是提供具有改进杀真菌活性的化合物。
我们发现该目的通过开头所定义的化合物实现。此外,我们还发现了制备它们的方法、包含它们的组合物以及使用化合物I防治植物病原性真菌的方法。
式I化合物与由最接近的现有技术-WO-A 98/46608已知的化合物的不同在于7-氟烷基氨基的具体定义,其中R3中的碳链由至少两个碳原子组成。
4-6元杂环基团可以是任何具有4-6个环原子且被一个或多个选自硫、氮和氧,优选氧的杂原子间隔的杂环基团。适合的卤素原子表示氟、氯或溴原子。
本发明进一步提供一种制备上面所定义的式I化合物的方法,包括用式III的胺处理其中X为卤素的式II的5,7-二卤代化合物:
5,7-二卤代化合物II与式III的胺之间的反应可以在由WO-A 98/46608已知的条件下进行。
该反应优选在溶剂存在下进行。合适的溶剂包括醚类,如二噁烷、乙醚,以及尤其是四氢呋喃,卤代烃类如二氯甲烷和芳族烃如甲苯。
该反应合适的是在0-70℃的温度下进行,优选的反应温度为10-35℃。
还优选该反应在碱存在下进行。合适的碱包括叔胺类,如三乙胺,以及无机碱,如碳酸钾或碳酸钠。另外,过量的式III化合物可以用作碱。
在本发明的其他实施方案中,通过与游离或配位金属原子如锂、钠或铜进行配位而活化胺III并使用配位的胺III’进行II的反应。在式III’中,M表示游离或配位的金属原子。反应条件通常与上述类似。
反应混合物以常规方式后处理,例如通过与水混合,分离各相以及需要的话,用色谱法提纯粗产物。一些终产物以无色或浅棕色粘稠油形式得到,将它们在减压和温和升高的温度下提纯或除去挥发性组分。若终产物以固体得到,则也可通过重结晶或溶解进行提纯。
式II化合物在本领域是已知的且可以通过EP-A 550 113和WO-A98/46608中公开的合成途径得到。
若经由上述途径不能得到单一化合物I,则它们可以通过衍生其它化合物I而制备。
在对上面各式所给符号的定义中,使用通常代表下列取代基的集合性术语:
-卤素:氟、氯、溴和碘;
-C1-C10-烷基和C1-C10-卤代烷基的烷基部分:具有1-10个,尤其1-6个碳原子的饱和的直链或支化烃基,例如上述C1-C4-烷基或戊基、1-甲基丁基、2-甲基丁基、3-甲基丁基、2,2-二甲基丙基、1-乙基丙基、己基、1,1-二甲基丙基、1,2-二甲基丙基、1-甲基戊基、2-甲基戊基、3-甲基戊基、4-甲基戊基、1,1-二甲基丁基、1,2-二甲基丁基、1,3-二甲基丁基、2,2-二甲基丁基、2,3-二甲基丁基、3,3-二甲基丁基、1-乙基丁基、2-乙基丁基、1,1,2-三甲基丙基、1,2,2-三甲基丙基、1-乙基-1-甲基丙基和1-乙基-2-甲基丙基;
-C1-C6-卤代烷基和C1-C6-卤代烷氧基的卤代烷基部分:具有1-6个,优选1-4个碳原子的直链或支化烷基(如上所述),其中这些基团中的氢原子可以被上述卤素原子部分或全部替代,例如C1-C2-卤代烷基,如氯甲基、溴甲基、二氯甲基、三氯甲基、氟甲基、二氟甲基、三氟甲基、氯氟甲基、二氯一氟甲基、一氯二氟甲基、1-氯乙基、1-溴乙基、1-氟乙基、2-氟乙基、2,2-二氟乙基、2,2,2-三氟乙基、2-氯-2-氟乙基、2-氯-2,2-二氟乙基、2,2-二氯-2-氟乙基、2,2,2-三氯乙基和五氟乙基;
-C1-C6-氟烷基和C1-C6-氟烷氧基的氟烷基部分:具有1-6个,优选1-4个碳原子的直链或支化烷基(如上所述),其中这些基团中的氢原子可以被上述氟原子部分或全部替代,例如C1-C2-氟烷基,如氟甲基、二氟甲基、三氟甲基、1-氟乙基、2-氟乙基、2,2-二氟乙基、2,2,2-三氟乙基和五氟乙基;
-C2-C10-链烯基:具有2-10个,优选3-6个碳原子且在任何位置具有双键的不饱和的直链或支化烃基,例如1-丙烯基、2-丙烯基、1-甲基乙烯基、1-丁烯基、2-丁烯基、3-丁烯基、1-甲基-1-丙烯基、2-甲基-1-丙烯基、1-甲基-2-丙烯基和2-甲基-2-丙烯基;
-C2-C10-炔基:具有2-10个,尤其是2-4个碳原子且在任何位置具有叁键的直链或支化烃基,例如乙炔基、1-丙炔基、2-丙炔基、1-丁炔基、2-丁炔基、3-丁炔基和1-甲基-2-丙炔基。
对于它们的意欲用途,优选具有下列取代基的式I三唑并嘧啶,其中优选情况在每种情况下无论是单独还是组合均有效:
对中间体的各变量而言,尤其优选的实施方案对应于式I的基团X、R1和R2的那些。
优选的烷基部分为乙基或尤其是甲基。
优选的卤代烷基部分为2,2,2-三氟乙基或1,1,1-三氟丙-2-基;
优选的链烯基部分为烯丙基或尤其是2-甲基烯丙基。
同样,还优选其中R1不为氢的式I化合物。
优选其中R1代表氟或直链或支化C1-C10-烷基,尤其是支化C3-C10-烷基的式I化合物。
此外,特别优选其中R1为氟的化合物I。
特别优选其中R2代表氢原子、C1-C10-烷基或C1-C10-卤代烷基,尤其是氢原子的化合物I。
此外,特别优选其中R2为氢的化合物I。
此外,特别优选其中R2为甲基的化合物I。
特别优选其中R3代表基团A的化合物I:
其中
Y1为氢、氟或C1-C6-氟烷基,
Y2为氢或氟,或
Y1和Y2结合在一起形成双键,和
m为0或1。
若R3代表C1-C10-卤代烷基,优选全氟烷基,尤其是2,2,2-三氟乙基、2-(1,1,1-三氟丙基)或2-(1,1,1-三氟丁基),则R2优选代表氢原子。
Ln优选为卤素或C1-C6-烷氧基。优选的实施方案为如下式I化合物:其中
代表
其中#表示与三唑并嘧啶部分的连接,L1-L4各自独立地表示氢,尤其是氟、氯、甲基或甲氧基,特别是其中L1为氟,L2为氢或氟,L3为氢或氟或甲氧基且L4表示氢、氟、氯或甲基。
此外,特别优选其中n为2或3的式I化合物。最优选L4不为氢。
此外,特别优选其中R1-R3具有式I所定义的含义且L1-L4具有上述含义的式IA化合物。
特别优选其中L1代表卤素,而L3和L4各自独立地代表氢、卤素或C1-C4-烷氧基的式IA化合物。
最优选其中L1为氟,L3为氢且L4为氯的式IA化合物。
特别优选其中R2为氢,L1和L4独立地代表氟或氯原子且L3代表氢、氟、氯或甲氧基的式IA化合物。
包括在本发明范围内的还有具有手性中心的通式I化合物的(R)和(S)异构体及其外消旋体,以及它们的盐、N-氧化物和酸加成化合物。
对于它们的应用,特别优选的是汇总在下面各表中的化合物I。在下面各表中,对于取代基提到的基团额外构成该取代基本身的尤其优选的实施方案,与其中提到它们的组合无关。
表1
其中L1为氟,L3为氢,L4为氯且R1、R2和R3对应于表A中的一行的式IA化合物
表2
其中L1和L4各自为氟,L3为氢且R1、R2和R3对应于表A中的一行的式IA化合物
表3
其中L1和L4各自为氯,L3为氢且R1、R2和R3对应于表A中的一行的式IA化合物
表4
其中L1为甲基,L3为氢,L4为氟且R1、R2和R3对应于表A中的一行的式IA化合物
表5
其中L1、L3和L4各自为氟且R1、R2和R3对应于表A中的一行的式IA化合物
表6
其中L1和L4各自为氟,L3为甲氧基且R1、R2和R3对应于表A中的一行的式IA化合物
表7
其中L1和L3各自为氢,L4为氟且R1、R2和R3对应于表A中的一行的式IA化合物
表8
其中L1和L3各自为氢,L4为氯且R1、R2和R3对应于表A中的一行的式IA化合物
表9
其中Ln为2-F-5-NO2,X为氯且R1、R2和R3对应于表A中的一行的式I化合物
表10
其中Ln为五氟,X为氯且R1、R2和R3对应于表A中的一行的式I化合物
表A
序号 | R1 | R2 | R3 |
A-1 | F | H | CH2CF3 |
A-2 | F | CH3 | CH2CF3 |
A-3 | F | CH2CH3 | CH2CF3 |
A-4 | F | CH2CH2CH3 | CH2CF3 |
A-5 | F | H | CH2C(CF3)=CH2 |
A-6 | F | CH3 | CH2C(CF3)=CH2 |
A-7 | F | CH2CH3 | CH2C(CF3)=CH2 |
A-8 | F | H | CH2C(CH3)=CF2 |
A-9 | F | CH3 | CH2C(CH3)=CF2 |
A-10 | F | CH2CH3 | CH2C(CH3)=CF2 |
A-11 | F | H | CH2CF=CH2 |
A-12 | F | CH3 | CH2CF=CH2 |
A-13 | F | CH2CH3 | CH2CF=CH2 |
A-14 | F | H | CH2CH=CF2 |
A-15 | F | CH3 | CH2CH=CF2 |
A-16 | F | CH2CH3 | CH2CH=CF2 |
A-17 | H | H | CF2CF3 |
A-18 | H | CH3 | CF2CF3 |
A-19 | H | CH2CH3 | CF2CF3 |
A-20 | H | CH2CH2CH3 | CF2CF3 |
A-21 | H | H | CHFCF3 |
A-22 | H | CH3 | CHFCF3 |
A-23 | H | CH2CH3 | CHFCF3 |
A-24 | H | CH2CH2CH3 | CHFCF3 |
A-25 | H | H | CH2CF2CF3 |
A-26 | H | CH3 | CH2CF2CF3 |
A-27 | H | CH2CH3 | CH2CF2CF3 |
A-28 | H | CH2CH2CH3 | CH2CF2CF3 |
A-29 | H | H | CH(CH3)CH2CF3 |
A-30 | H | CH3 | CH(CH3)CH2CF3 |
A-31 | H | CH2CH3 | CH(CH3)CH2CF3 |
A-32 | H | CH2CH2CH3 | CH(CH3)CH2CF3 |
A-33 | H | H | CH2CH=CF2 |
A-34 | H | CH3 | CH2CH=CF2 |
A-35 | H | CH2CH3 | CH2CH=CF2 |
A-36 | H | CH2CH2CH3 | CH2CH=CF2 |
A-37 | H | H | CH2CF=CF2 |
A-38 | H | CH3 | CH2CF=CF2 |
A-39 | H | CH2CH3 | CH2CF=CF2 |
A-40 | H | CH2CH2CH3 | CH2CF=CF2 |
化合物I适于作为杀真菌剂。它们对宽范围的植物病原性真菌具有显著的活性,所述真菌尤其选自子囊菌纲(Ascomycetes)、半知菌纲(Deuteromycetes)、藻菌纲(Phycomycetes)和担子菌纲(Basidiomycetes)真菌。它们中的一些起内吸作用并可以作为叶面和土壤作用杀真菌剂用于作物保护中。
它们对在各种作物如小麦、黑麦、大麦、燕麦、稻、玉米、禾草、香蕉、棉花、大豆、咖啡、甘蔗、葡萄藤、水果品种、观赏植物和蔬菜如黄瓜、豆类、西红柿、土豆和葫芦科植物以及这些植物的种子中防治大量真菌尤其重要。
具体而言,它们适于防治下列植物病害:
蔬菜和水果上的链格孢(Alternaria)属,
草莓、蔬菜、观赏植物和葡萄藤上的Botrytis cinerea(灰霉病),
花生上的落花生尾孢(Cercospora arachidicola),
葫芦科植物上的二孢白粉菌(Erysiphe cichoracearum)和单丝壳(Sphaerotheca fuliginea),
禾谷类上的Blumeria graminis(白粉病),
各种植物上的链孢霉(Fusarium)和轮枝孢(Verticillium)属,
禾谷类上的长蠕孢(Helminthosporium)属,
香蕉和花生上的球腔菌(Mycosphaerella)属,
土豆和西红柿上的致病疫霉(Phytophthora infestans),
葡萄藤上的葡萄生单轴霉(Plasmopara viticola),
苹果上的苹果白粉病菌(Podosphaera leucotricha),
小麦和大麦上的眼斑病菌(Pseudocercosporella herpotrichoides),
啤酒花和黄瓜上的假霜霉(Pseudoperonospora)属,
禾谷类上的柄锈菌(Puccinia)属,
稻上的稻瘟病菌(Pyricularia oryzae),
棉花、稻和草坪上的丝核菌(Rhizoctonia)属,
禾谷类上的壳针孢(Septoria)属,
葡萄藤上的葡萄钩丝壳(Uncinula necator),
禾谷类和甘蔗上的黑粉菌(Ustilago)属,以及
苹果和梨上的Venturia属(黑星病)。
此外,化合物I还适于防治有害真菌如拟青霉(Paecilomyces variotii)以保护材料(如木材、纸张、漆分散体、纤维和织物)和保护储藏的产品。
化合物I通过用杀真菌有效量的活性成分处理真菌或需要防止真菌侵染的植物、种子、材料或土壤而施用。施用可以在材料、植物或种子被真菌侵染之前或之后进行。
通常而言,杀真菌组合物包含0.1-95重量%,优选0.5-90重量%的活性成分。
当用于作物保护时,施用率取决于所需效果的性质为0.01-2.0kg活性成分/公顷。
在处理种子时,每kg种子通常需要的活性成分量为0.001-0.1g,优选0.01-0.05g。
当用于保护材料或储藏产品时,活性成分的施用率取决于施用场地的性质和所需效果。在保护材料中通常使用的施用率例如为0.001g至2kg,优选0.005g至1kg活性成分/m3处理材料。
可以将化合物I转化成常规配制剂,例如溶液、乳液、悬浮液、粉剂、粉末、糊和粒剂。使用形式取决于具体的目的;在每种情况下都应确保本发明化合物精细和均匀地分布。
配制剂以已知方式制备,例如通过将活性成分与溶剂和/或载体混合来制备,需要的话使用乳化剂和分散剂,若使用水作为稀释剂,则还可以使用其它有机溶剂作为辅助溶剂。适合的助剂主要是溶剂如芳族溶剂(如二甲苯),氯代芳族溶剂(如氯苯),链烷烃(如矿物油馏分),醇(如甲醇、丁醇),酮(如环己酮),胺(如乙醇胺、二甲基甲酰胺)和水;载体如磨碎的天然矿物(如高岭土、粘土、滑石、白垩)和磨碎的合成矿物(如高度分散的硅石、硅酸盐);乳化剂如非离子和阴离子乳化剂(如聚氧乙烯脂肪醇醚、烷基磺酸盐和芳基磺酸盐)以及分散剂如木素亚硫酸盐废液和甲基纤维素。
合适的表面活性剂是木质素磺酸、萘磺酸、苯酚磺酸、二丁基萘磺酸的碱金属盐、碱土金属盐和铵盐,烷基芳基磺酸盐,烷基硫酸盐,烷基磺酸盐,脂肪醇硫酸盐以及脂肪酸及其碱金属和碱土金属盐,硫酸化脂肪醇乙二醇醚的盐,磺化萘和萘衍生物与甲醛的缩合物,萘或萘磺酸与苯酚或甲醛的缩合物,聚氧乙烯辛基苯基醚,乙氧基化的异辛基酚、辛基酚、壬基酚,烷基酚聚乙二醇醚,三丁基苯基聚乙二醇醚,烷基芳基聚醚醇,异十三烷醇,脂肪醇/氧化乙烯缩合物,乙氧基化蓖麻油,聚氧乙烯烷基醚,乙氧基化聚氧丙烯,月桂醇聚乙二醇醚缩醛,山梨醇酯,木素亚硫酸盐废液和甲基纤维素。
适于制备直接可喷雾溶液、乳液、糊或油分散体的物质是中沸点到高沸点的矿物油馏分,如煤油或柴油,此外还有煤焦油和植物或动物来源的油,脂族、环状和芳族烃,例如苯、甲苯、二甲苯、石蜡、四氢化萘、烷基化萘或其衍生物、甲醇、乙醇、丙醇、丁醇、氯仿、四氯化碳、环己醇、环己酮、氯苯、异佛尔酮,强极性溶剂,例如二甲基甲酰胺、二甲亚砜、N-甲基吡咯烷酮和水。
粉末、撒播用材料和粉剂可以通过将活性物质与固体载体混合或同时研磨而制备。
粒剂如包膜粒剂、浸渍粒剂和均相粒剂可以通过将活性成分与固体载体粘附而制备。固体载体的实例是矿土如硅石、硅胶、硅酸盐、滑石、高岭土、Attaclay、石灰石、石灰、白垩、红玄武土、黄土、粘土、白云石、硅藻土、硫酸钙、硫酸镁、氧化镁;磨碎的合成材料;肥料如硫酸铵、磷酸铵、硝酸铵、尿素;植物来源的产品如谷粉、树皮粉、木粉和坚果壳粉;纤维素粉和其它固体载体。
通常而言,配制剂包含0.01-95重量%,优选0.1-90重量%的活性成分。活性成分以90-100%,优选95-100%的纯度(根据NMR光谱)使用。
下列为配制剂的实例:
I.将5重量份本发明化合物与95重量份细碎高岭土均匀混合。这得到包含5重量%活性成分的粉剂。
II.将30重量份本发明化合物与92重量份粉状硅胶和8重量份喷雾于该硅胶表面上的石蜡油的混合物均匀混合。这得到具有良好粘附性能的活性成分配制剂(包含23重量%活性成分)。
III.将10重量份本发明化合物溶于由90重量份二甲苯、6重量份的8-10mol氧化乙烯与1mol油酸N-单乙醇酰胺的加合物、2重量份十二烷基苯磺酸钙和2重量份的40mol氧化乙烯与1mol蓖麻油的加合物组成的混合物中(包含9重量%活性成分)。
IV.将20重量份本发明化合物溶于由60重量份环己酮、30重量份异丁醇、5重量份的7mol氧化乙烯与1mol异辛基苯酚的加合物和5重量份的40mol氧化乙烯与1mol蓖麻油的加合物组成的混合物中(包含16重量%活性成分)。
V.将80重量份本发明化合物与3重量份二异丁基萘-α-磺酸钠、10重量份来自亚硫酸盐废液的木质素磺酸的钠盐和7重量份粉状硅胶彻底混合,并将该混合物(包含80重量%活性成分)在锤磨机中研磨。
VI.将90重量份本发明化合物与10重量份N-甲基-α-吡咯烷酮混合,得到适于以微滴形式使用的溶液(包含90重量%活性成分)。
VII.将20重量份本发明化合物溶于由40重量份环己酮、30重量份异丁醇、20重量份的7mol氧化乙烯与1mol异辛基苯酚的加合物以及10重量份的40mol氧化乙烯与1mol蓖麻油的加合物组成的混合物中。将该溶液倾入100,000重量份水中并使其在其中精细分布,得到包含0.02重量%活性成分的水分散体。
VIII.将20重量份本发明化合物与3重量份二异丁基萘-α-磺酸钠、17重量份来自亚硫酸盐废液的木质素磺酸的钠盐和60重量份粉状硅胶彻底混合,并将该混合物在锤磨机中研磨。将该混合物精细地分布在20,000重量份水中,得到包含0.1重量%活性成分的喷雾混合物。
活性成分可以通过喷雾、雾化、撒粉、撒播或浇灌直接使用,以其配制剂形式或由其制备的使用形式使用,例如以直接可喷溶液、粉剂、悬浮液或分散体、乳液、油分散体、糊、粉末、撒播用材料或粒剂形式使用。使用形式完全取决于意欲的目的;在各种情况下都应确保本发明的活性成分尽可能精细地分布。
含水使用形式可以通过添加水由乳油、糊或可湿性粉剂(可喷雾粉剂、油分散体)制备。为了制备乳液、糊或油分散体,可以通过湿润剂、增稠剂、分散剂或乳化剂将物质直接或溶于油或溶剂之后在水中均化。作为选择,可以制备由活性物质、湿润剂、增稠剂、分散剂或乳化剂以及合适的话,溶剂或油组成的浓缩物且该类浓缩物适于用水稀释。
活性成分在即用产品中的浓度可以在较宽范围内变化。它们通常为0.0001-10%,优选0.01-1%。
活性成分还可成功地以超低容量方法(ULV)使用,其中可以施用包含超过95重量%活性成分的配制剂或甚至可以在没有添加剂的情况下施用活性成分。
可以将各种类型的油、除草剂、杀真菌剂、其它杀虫剂或杀菌剂加入活性成分中,合适的话在紧临使用之前(桶混合)加入。这些试剂可以与本发明试剂以1∶10至10∶1的重量比混合。
在作为杀真菌剂的使用形式中,本发明组合物还可与其它活性成分一起存在,例如与除草剂、杀虫剂、生长调节剂、杀真菌剂或肥料一起存在。将作为杀真菌剂的化合物I或包含它们的组合物与其它杀真菌剂混合通常产生更宽的杀真菌作用谱。
下列本发明化合物可以与其一起使用的杀真菌剂用来阐述可能的组合,而不施以任何限制:
硫,二硫代氨基甲酸盐及其衍生物,例如二甲基二硫代氨基甲酸铁(III)、二甲基二硫代氨基甲酸锌、亚乙基双-二硫代氨基甲酸锌、亚乙基双-二硫代氨基甲酸锰、乙二胺双-二硫代氨基甲酸锰锌、四甲基秋兰姆二硫化物、(N,N-亚乙基双-二硫代氨基甲酸)锌的氨配合物、(N,N’-亚丙基双-二硫代氨基甲酸)锌的氨配合物、(N,N’-亚丙基双-二硫代氨基甲酸)锌、N,N’-聚亚丙基双(硫代氨基甲酰基)二硫化物;
硝基衍生物,例如巴豆酸二硝基(1-甲基庚基)苯基酯、3,3-二甲基丙烯酸2-仲丁基-4,6-二硝基苯基酯、碳酸2-仲丁基-4,6-二硝基苯基异丙基酯、5-硝基-间苯二甲酸二异丙基酯;
杂环物质,例如乙酸2-十七烷基-2-咪唑啉酯、2,4-二氯-6-(邻氯苯胺基)-s-三嗪、邻苯二甲酰亚胺基硫代膦酸O,O-二乙基酯、5-氨基-1-[双(二甲基氨基)膦基]-3-苯基-1,2,4-三唑、2,3-二氰基-1,4-二硫代蒽醌、2-硫代-1,3-二硫杂环戊二烯并[4,5-b]-喹喔啉、1-(丁基氨基甲酰基)-2-苯并咪唑氨基甲酸甲酯、2-甲氧基羰基氨基苯并咪唑、2-(2-呋喃基)-苯并咪唑、2-(4-噻唑基)苯并咪唑、N-(1,1,2,2-四氯乙硫基)四氢邻苯二甲酰亚胺、N-三氯甲硫基四氢邻苯二甲酰亚胺、N-三氯甲硫基邻苯二甲酰亚胺;
N-二氯一氟甲硫基-N’,N’-二甲基-N-苯基磺基二酰胺、5-乙氧基-3-三氯甲基-1,2,3-噻二唑、2-硫氰酸基甲硫基苯并噻唑、1,4-二氯-2,5-二甲氧基苯、4-(2-氯苯基亚肼基)-3-甲基-5-异噁唑酮、吡啶-2-硫醇1-氧化物、8-羟基喹啉或其铜盐、2,3-二氢-5-甲酰苯胺基-6-甲基-1,4-氧硫杂环己二烯、2,3-二氢-5-甲酰苯胺基-6-甲基-1,4-氧硫杂环己二烯4,4-二氧化物、2-甲基-5,6-二氢-4H-吡喃-3-甲酰苯胺、2-甲基呋喃-3-甲酰苯胺、2,5-二甲基呋喃-3-甲酰苯胺、2,4,5-三甲基呋喃-3-甲酰苯胺、N-环己基-2,5-二甲基呋喃-3-甲酰胺、N-环己基-N-甲氧基-2,5-二甲基呋喃-3-甲酰胺、2-甲基苯甲酰苯胺、2-碘代苯甲酰苯胺、N-甲酰基-N-吗啉-2,2,2-三氯乙基缩醛、哌嗪-1,4-二基双-1-(2,2,2-三氯乙基)甲酰胺、1-(3,4-二氯苯胺基)-1-甲酰基氨基-2,2,2-三氯乙烷、2,6-二甲基-N-十三烷基吗啉或其盐、2,6-二甲基-N-环十二烷基吗啉或其盐、N-[3-(对叔丁基苯基)-2-甲基丙基]-顺式-2,6-二甲基吗啉、N-[3-(对叔丁基苯基)-2-甲基丙基]哌啶、1-[2-(2,4-二氯苯基)-4-乙基-1,3-二氧戊环-2-基-乙基]-1H-1,2,4-三唑、1-[2-(2,4-二氯苯基)-4-正丙基-1,3-二氧戊环-2-基-乙基]-1H-1,2,4-三唑、N-(正丙基)-N-(2,4,6-三氯苯氧基乙基)-N’-咪唑基脲、1-(4-氯苯氧基)-3,3-二甲基-1-(1H-1,2,4-三唑-1-基)-2-丁酮、1-(4-氯苯氧基)-3,3-二甲基-1-(1H-1,2,4-三唑-1-基)-2-丁醇、(2RS,3RS)-1-[3-(2-氯苯基)-2-(4-氟苯基)-氧化乙烯-2-基甲基]-1H-1,2,4-三唑、α-(2-氯苯基)-α-(4-氯苯基)-5-嘧啶甲醇、5-丁基-2-二甲基氨基-4-羟基-6-甲基嘧啶、双(对氯苯基)-3-吡啶甲醇、1,2-双(3-乙氧基羰基-2-硫脲基)苯、1,2-双(3-甲氧基羰基-2-硫脲基)苯;
嗜球果伞素,例如密菌胺(azoxystrobin)、醚菌酯(kresoxim methyl)、甲基-E-甲氧亚氨基-[α-(2-苯氧基苯基)]乙酰胺、甲基-E-甲氧亚氨基-[α-(2,5-二甲基苯氧基)-邻甲苯基]乙酰胺、啶氧菌酯(picoxystrobin)、氟环唑十(pyraclostrobin)、肟菌酯(trifloxystrobin);
苯胺基嘧啶,例如N-(4,6-二甲基嘧啶-2-基)苯胺、N-[4-甲基-6-(1-丙炔基)嘧啶-2-基]苯胺、N-[4-甲基-6-环丙基嘧啶-2-基]苯胺;
苯基吡咯,例如4-(2,2-二氟-1,3-苯并二氧杂环戊烯-4-基)吡咯-3-甲腈;
肉桂酰胺,例如3-(4-氯苯基)-3-(3,4-二甲氧基苯基)丙烯酰基吗啉;和
各种杀真菌剂,例如乙酸十二烷基胍、3-[3-(3,5-二甲基-2-氧基环己基)-2-羟乙基]戊二酰亚胺、六氯苯、N-(2,6-二甲基苯基)-N-(2-呋喃甲酰基)-DL-丙氨酸甲酯、DL-N-(2,6-二甲基苯基)-N-(2’-甲氧基乙酰基)-丙氨酸甲酯、N-(2,6-二甲基苯基)-N-氯乙酰基-D,L-2-氨基-丁内酯、DL-N-(2,6-二甲基苯基)-N-(苯基乙酰基)-丙氨酸甲酯、5-甲基-5-乙烯基-3-(3,5-二氯苯基)-2,4-二氧代-1,3-噁唑烷、3-[3,5-二氯苯基(5-甲基-5-甲氧基甲基)-1,3-噁唑烷-2,4-二酮、3-(3,5-二氯苯基)-1-异丙基氨基甲酰基乙内酰脲、N-(3,5-二氯苯基)-1,2-二甲基环丙烷-1,2-二甲酰亚胺、2-氰基-[N-(乙基氨基羰基)-2-甲氧亚氨基]乙酰胺、1-[2-(2,4-二氯苯基)戊基]-1H-1,2,4-三唑、2,4-二氟-α-(1H-1,2,4-三唑基-1-甲基)二苯甲醇、N-(3-氯-2,6-二硝基-4-三氟甲基苯基)-5-三氟甲基-3-氯-2-氨基吡啶、1-((双(4-氟苯基)甲基甲硅烷基)甲基-1H-1,2,4-三唑。
合成实施例
通过适当改变起始化合物,使用下列合成实施例中所示的程序得到其它化合物I。所得化合物与物理数据一起列于下面的表中。
实施例1:制备5-氯-6-(2-氯-6-氟苯基)-7-(1,1,1-三氟丁-4-基)-氨基-[1,2,4]-三唑并[1,5-a]嘧啶[I-9]
将1.5mmol 1,1,1-三氟丁烷-4-胺、1.5mmol三乙胺在10ml二氯甲烷中的溶液加入1.5mmol 5,7-二氯-6-(2-氯-6-氟苯基)-[1,2,4]-三唑并[1,5-a]嘧啶[参见EP-A 550113]在20ml二氯甲烷中的溶液中。将合并的溶液在20-25℃下搅拌约16小时,然后用稀(5%)盐酸洗涤。分离有机相,干燥并过滤。从滤液中蒸馏除去溶剂并在硅胶上进行层析得到0.45g标题化合物,熔点为115℃。
表I
序号 | R1 | R2 | R3 | Ln | 物理数据(m.p.[℃]) |
I-1 | H | H | CHFCF3 | 2,4,6-F3 | 189 |
I-2 | H | H | CH2CF=CF2 | 2,4,6-F3 | 137 |
I-3 | H | H | C(CH3)CH2CF3 | 2,4,6-F3 | 143 |
I-4 | F | H | CH2CF3 | F5 | 200 |
I-5 | H | H | CH2CF3 | 2,4,6-F3 | 202 |
I-6 | H | H | CF2CF3 | 2-Cl-6-F | 140 |
I-7 | H | H | CH2CF3 | 2,6-F2-4-OCH3 | 161 |
I-8 | H | H | CF2CF2CF3 | 2-Cl-6-F | 182 |
I-9 | H | H | CH2CH2CF3 | 2-Cl-6-F | 115 |
I-10 | H | H | CH2CH2CF3 | 2,4,6-F3 | 142 |
I-11 | H | H | CH2CF=CF2 | 2,6-F2 | 130 |
I-12 | H | H | CH2CF=CF2 | 2-Cl | 129 |
I-13 | H | H | CH2CF=CF2 | 2-F | 111 |
I-14 | H | H | CH2CF=CF2 | 2-Cl-6-F | 107 |
I-15 | H | H | CH2CF=CF2 | F5 | 118 |
I-16 | H | H | CHFCF3 | 2-NO2-5-F | 浆状物 |
I-17 | H | H | CHFCF3 | 2-Cl-6-F | 199 |
I-18 | H | H | CHFCF3 | 2,6-F2 | 80 |
I-19 | H | H | CH2CH2CF3 | 2-F | 81 |
对有害真菌的作用实施例
式I化合物的杀真菌作用通过下列试验证实:
在70重量%环己酮、20重量%NekanilLN(LutensolAP6,基于乙氧基化烷基酚且具有乳化和分散作用的湿润剂)和10重量%WettolEM(基于乙氧基化蓖麻油的非离子乳化剂)的混合物中将活性化合物单独或一起配制成10%乳液并用水稀释至所需浓度。
应用实施例1:对苹果黑星病菌(Venturia inequalis)的杀真菌防治
将栽培品种为“Common”的苹果幼苗在盆中生长到4-5叶阶段。使用含水悬浮液将这些植物喷雾至滴流点,所述悬浮液含有下述浓度的活性成分且由含有5%活性化合物、94%环己酮和1%乳化剂(Tween 20)的储备溶液制备。在植物干燥后(3-5小时),将它们用苹果黑星病菌的含水孢子悬浮液接种。然后将试验植物立即转移到22-24℃和相对湿度接近100%的潮湿室中并栽培2天。然后在21-23℃和相对湿度约95%的温室中再栽培2周。然后以侵染叶面积%肉眼评价叶子上的真菌侵染程度。
在该试验中,用200ppm化合物I-1至I-6和I-8至I-19处理的植物显示出至多15%的侵染,而未处理植物显示出80%的侵染。
应用实施例2-对西红柿上的早疫病菌(Alternaria solani)的杀真菌防治
将栽培品种为“Pixie II”的西红柿幼苗在盆中生长到2-4叶阶段。使用含水悬浮液将这些植物喷雾至滴流点,所述悬浮液含有下述浓度的活性成分且由含有5%活性化合物、94%环己酮和1%乳化剂(Tween 20)的储备溶液制备。在植物干燥后(3-5小时),将它们用早疫病菌的含水孢子悬浮液(每ml含15×103个孢子)接种。然后将试验植物立即转移到22-24℃和相对湿度接近100%的潮湿室中并保持36小时。然后在21-23℃和相对湿度约95%的温室中再栽培2-3天。然后以侵染叶面积%肉眼评价叶子上的真菌侵染程度。
在该试验中,用200ppm化合物I-1至I-7、I-9至I-13、I-15、I-17和I-18处理的植物显示出至多15%的侵染,而未处理植物显示出90%的侵染。
应用实施例3:对甜菜上的甜菜生尾孢(Cercospora beticola)的杀真菌防治
将栽培品种为“ACH-31”的糖用甜菜幼苗在盆中生长到2-4叶阶段。使用含水悬浮液将这些植物喷雾至滴流点,所述悬浮液含有下述浓度的活性成分且由含有5%活性化合物、94%环己酮和1%乳化剂(Tween 20)的储备溶液制备。在植物干燥后(3-5小时),将它们用甜菜生尾孢在0.5%明胶水溶液中的孢子悬浮液接种。然后将试验植物立即转移到18-23℃和相对湿度接近100%的潮湿室中并在其中保持5天。然后在21-23℃和相对湿度约95%的温室中再栽培10-14天。然后以侵染叶面积%肉眼评价叶子上的真菌侵染程度。
在该试验中,用200ppm化合物I-1至I-4、I-6、I-8和I-11至I-19处理的植物显示出至多15%的侵染,而未处理植物显示85%的侵染。
对比试验
将分别由WO-A 98/46607、WO-A 98/46608和WO-A 99/48893已知的活性化合物A-E在下列对比试验中用作对比化合物:
序号 | 由如下文献已知 | R1 | Ln |
A | WO-A 98/46607,实施例12 | H | 2,4,6-F3 |
B | WO-A 98/46608,实施例1 | H | 2-Cl-6-F |
C | WO-A 98/46608,实施例5 | CH3 | 2,6-F2 |
D | WO-A 99/48893,实施例6 | H | 2,6-F2-4-OCH3 |
E | WO-A 99/48893,实施例7 | CH3 | 2,6-F2-4-OCH3 |
对比试验1:对由稻瘟病菌(Pyricularia oryzae)引起的稻瘟病的杀真菌防治(保护作用)
将栽培品种为“Tai-Nong 67”的盆栽稻秧苗的叶子用含水悬浮液喷雾至滴流,所述悬浮液含有下述浓度的活性成分且由含有10%活性化合物、85%环己酮和5%乳化剂的储备溶液制备。将植物风干。第二天将植物用含有1.0×106个孢子/ml的稻瘟病菌含水孢子悬浮液接种。然后将试验植物立即转移到潮湿室中。在22-24℃和相对湿度接近100%下6天后,以侵染叶面积%肉眼评价叶子上的真菌侵染程度。
在该试验中,分别用200ppm化合物I-1、I-2和I-3处理的植物显示出3%的侵染,而分别用200ppm对比化合物A、B和C处理的植物的侵染分别为60%、10%和20%,未处理植物的侵染为90%。
对比试验2:对由禾白粉菌(Blumeria graminis f.sp.tritici)引起的小麦白粉病的防治
将栽培品种为“Kanzler”的盆栽小麦的最早完全发育的叶子用含水悬浮液喷雾至滴流,所述悬浮液含有下表所述浓度的活性成分或其混合物且由含有10%活性化合物、85%环己酮和5%乳化剂的储备溶液制备。第二天通过在处理过的盆上振摇严重侵染的储备植物而将处理过的植物用禾白粉菌的孢子接种。在22-26℃和60-90%的相对湿度下于温室中栽培7天后以侵染叶面积%肉眼评价叶子上的真菌侵染程度。
在该试验中,分别用200和50ppm化合物I-7处理的植物分别显示出3%和7%的侵染,而分别用200和50ppm对比化合物D和E处理的植物显示出的侵染分别为60%和80%(在200ppm下)以及80%(在50ppm下),未处理植物100%侵染。
Claims (8)
1.式I的5-卤代-6-苯基-7-氟烷基氨基三唑并嘧啶:
其中
R1为氢、氟、C1-C10-烷基、C2-C10-链烯基、C2-C10-炔基、C2-C10-链烷二烯基,
其中这些基团的碳链可以未被取代或被部分或全部卤代或可以携带1-3个基团Ra,
Ra为氰基、硝基、羟基、C1-C6-烷基、C1-C6-卤代烷基、C1-C6-烷基羰基、C3-C6-环烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基、C1-C6-烷氧羰基、C1-C6-烷硫基、C1-C6-烷基氨基,
二-C1-C6-烷基氨基、C2-C6-链烯基、C2-C6-链烯氧基、C3-C6-炔氧基和
C1-C4-亚烷二氧基,其可以被卤代;R2为氢、C1-C10-烷基、C2-C10-链烯基、C2-C10-炔基、C2-C10-链烷二烯基,其中这些基团可以未被取代或被部分或全部卤代或可以携带1-3个基团Ra,
R3为C2-C8-氟烷基或C2-C8-氟链烯基;
X为卤素;
n为0或1-4的整数;
L各自独立地为卤素、硝基、C1-C10-烷基、C1-C6-卤代烷基、C1-C10-烷氧基或C1-C6-卤代烷氧基。
2.根据权利要求1的化合物,其中至少一个L基团为卤素。
3.根据权利要求1或2的化合物,其中R1为氢、氟或甲基。
4.根据权利要求1的化合物,其中R2为氢或C1-C10-烷基。
7.适于防治植物病原性真菌的组合物,包含固体或液体载体和如权利要求1所要求的式I化合物。
8.一种防治植物病原性真菌的方法,包括用有效量的如权利要求1所要求的式I化合物处理真菌或需要防止真菌侵染的材料、植物、土壤或种子。
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DE10124208A1 (de) † | 2001-05-18 | 2002-11-21 | Bayer Ag | Verwendung von Triazolopyrimidin-Derivaten als Mikrobizide |
DE50305076D1 (de) * | 2002-11-07 | 2006-10-26 | Basf Ag | 5-alkyl-7-aminotriazolopyrimidine,verfahren und zwischenprodukte zu ihrer herstellung ,sie enthaltende mittel sowie ihre verwendung zur bekämpfung von schadpilzen |
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MXPA06003206A (es) | 2003-09-24 | 2006-06-23 | Wyeth Corp | 6-[(sustituido)fenil]triazolopirimidinas como agentes anticancer. |
US7419982B2 (en) | 2003-09-24 | 2008-09-02 | Wyeth Holdings Corporation | Crystalline forms of 5-chloro-6-{2,6-difluoro-4-[3-(methylamino)propoxy]phenyl}-N-[(1S)-2,2,2-trifluoro-1-methylethyl][1,2,4]triazolo[1,5-a]pyrimidin-7-amine salts |
CA2537520A1 (en) | 2003-09-24 | 2005-04-07 | Wyeth Holdings Corporation | 6-aryl-7-halo-imidazo[1,2-a]pyrimidines as anticancer agents |
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