CN1313467C - 作为杀真菌剂的6-(2,6-二氟苯基)三唑并嘧啶 - Google Patents
作为杀真菌剂的6-(2,6-二氟苯基)三唑并嘧啶 Download PDFInfo
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- CN1313467C CN1313467C CNB028144112A CN02814411A CN1313467C CN 1313467 C CN1313467 C CN 1313467C CN B028144112 A CNB028144112 A CN B028144112A CN 02814411 A CN02814411 A CN 02814411A CN 1313467 C CN1313467 C CN 1313467C
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- methyl
- alkyl
- difluorophenyl
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- LRBIIDOZKPXQOL-UHFFFAOYSA-N 6-(2,6-difluorophenyl)triazolo[4,5-d]pyrimidine Chemical class FC1=CC=CC(F)=C1N1C=C2N=NN=C2N=C1 LRBIIDOZKPXQOL-UHFFFAOYSA-N 0.000 title abstract 2
- 239000000203 mixture Substances 0.000 claims abstract description 26
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 24
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims abstract description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 6
- 125000005843 halogen group Chemical group 0.000 claims abstract description 4
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- 239000000463 material Substances 0.000 claims description 14
- YWBFPKPWMSWWEA-UHFFFAOYSA-O triazolopyrimidine Chemical compound BrC1=CC=CC(C=2N=C3N=CN[N+]3=C(NCC=3C=CN=CC=3)C=2)=C1 YWBFPKPWMSWWEA-UHFFFAOYSA-O 0.000 claims description 8
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
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- WHDGWKAJBYRJJL-UHFFFAOYSA-K ferbam Chemical compound [Fe+3].CN(C)C([S-])=S.CN(C)C([S-])=S.CN(C)C([S-])=S WHDGWKAJBYRJJL-UHFFFAOYSA-K 0.000 description 4
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- 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
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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
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
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- Chemical & Material Sciences (AREA)
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- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
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- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (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6-(2,6-二氟苯基)三唑并嘧啶,其中R1和R2独立地表示氢或烷基、链烯基、炔基或链二烯基、环烷基、苯基、萘基或含有1-4个氮原子或含有1-3个氮原子和1个硫原子或氧原子的5或6元杂环基,或含有1-4个氮原子或含有1-3个氮原子和1个硫原子或氧原子的5或6元杂芳基,其中基团R1和R2可以是未取代的或如说明书中所定义的那样被取代,或R1和R2与其相邻氮原子一起代表含有1-4个氮原子或含有1-3个氮原子和1个硫原子或氧原子且可以被取代的5或6元杂环;X为卤素、氰基、烷氧基、卤代烷氧基或链烯氧基。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。
Description
本发明涉及式I的6-(2,6-二氟苯基)三唑并嘧啶:
其中
R1和R2独立地表示氢或
C1-C10-烷基、C2-C10-链烯基、C2-C10-炔基或C4-C10-链二烯基、C3-C10-环烷基、苯基、萘基,或
5或6元杂环基,其含有1-4个氮原子或含有1-3个氮原子和1个硫原子或氧原子,或
5或6元杂芳基,其含有1-4个氮原子或含有1-3个氮原子和1个硫原子或氧原子,或
其中基团R1和R2可以是未取代的或可以带有1-3个基团Ra,
Ra为氰基、硝基、羟基、C1-C6-烷基、C3-C6-环烷基、C1-C6-烷氧基、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、C2-C6-炔基、C3-C6-炔氧基和C1-C4-亚烷基二氧基;或
R1和R2与其相邻氮原子一起代表5或6元杂环,其含有1-4个氮原子或含有1-3个氮原子和1个硫原子或氧原子且可以被1-3个基团Ra取代;
X为卤素、氰基、C1-C6-烷氧基、C1-C6-卤代烷氧基或C3-C8-链烯氧基。
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。
6-苯基-7-氨基三唑并嘧啶通常由US 4,567,262和US 5,593,996已知。
在6位上带有三氟苯基的三唑并嘧啶公开在WO-A 98/46607和EP-A945453中。
由WO-A 98/46608已知某些6-(2,6-二氟苯基)三唑并嘧啶,它们在7位上被氟化烷基胺取代。
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,我们还发现了它们的制备方法、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WO-A 98/46608已知的化合物的不同之处在于,在该三唑并嘧啶体系的7位上2,6-二氟苯基与不含卤素的氨基的结合。
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。
式II化合物由EP-A 550 113已知。它们可以通过已知方法制备[参见EP-A 550 113或EP-A 770 615]。
该反应优选在溶剂存在下进行。合适的溶剂包括醚类,如二烷、乙醚,以及尤其是四氢呋喃,卤代烃类如二氯甲烷和芳族烃类如甲苯。
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。
反应混合物以常规方式后处理,例如通过与水混合,相分离以及需要的话,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化合物在本领域中是已知的且可以通过EP-A 550 113、EP-A770 615和WO-A 98/46608中公开的合成途径得到。
其中X代表氰基、C1-C6-烷氧基、C1-C6-卤代烷氧基或C3-C8-链烯氧基的式I化合物可以通过使其中X为卤素,优选氯的化合物I与式IV化合物优选在溶剂存在下反应而制备,式IV化合物取决于待引入以得到式I化合物的X’而分别为无机氰基盐、烷氧基化物、卤代烷氧基化物或链烯氧基化物。式IV中的阳离子M具有较小的影响。考虑到实践和经济上的原因,通常优选铵盐、四烷基铵盐或碱金属盐和碱土金属盐。
该反应合适的是在0-120℃,优选10-40℃的温度下进行[参见J.Heterocycl.Chem.(杂环化学杂志),第12卷,第861-863页(1975)]。
合适的溶剂包括醚类,如二烷、乙醚,以及尤其是四氢呋喃,卤代烃类如二氯甲烷和芳族烃类如甲苯。
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: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;
-C2-C10-链烯基:具有2-10个,优选2-6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,例如乙烯基、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;
-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-卤代烷氧基,如氯甲氧基、溴甲氧基、二氯甲氧基、三氯甲氧基、氟甲氧基、二氟甲氧基、三氟甲氧基、氯氟甲氧基、二氯一氟甲氧基、一氯二氟甲氧基、1-氯乙氧基、1-溴乙氧基、1-氟乙氧基、2-氟乙氧基、2,2-二氟乙氧基、2,2,2-三氟乙氧基、2-氯-2-氟乙氧基、2-氯-2,2-二氟乙氧基、2,2-二氯-2-氟乙氧基、2,2,2-三氯乙氧基和五氟乙氧基;
-C3-C10-环烷基:具有3-10个碳原子的单环或双环环烷基;单环基团优选具有3-8个,尤其是3-6个环成员,双环基团优选具有8-10个环成员。
5或6元杂环基,其含有1-4个氮原子或含有1-3个氮原子和1个硫原子或氧原子,优选1个氧原子。
含有1-4个氮原子或含有1-3个氮原子和1个硫原子或氧原子的5元杂芳基:除碳原子外还可含有1-4个氮原子或含有1-3个氮原子和1个硫原子或氧原子作为环成员的5元杂芳基,例如2-呋喃基、3-呋喃基、2-噻吩基、3-噻吩基、2-吡咯基、3-吡咯基、3-异唑基、4-异唑基、5-异唑基、3-异噻唑基、4-异噻唑基、5-异噻唑基、3-吡唑基、4-吡唑基、5-吡唑基、2-唑基、4-唑基、5-唑基、2-噻唑基、4-噻唑基、5-噻唑基、2-咪唑基、4-咪唑基、1,2,4-二唑-3-基、1,2,4-二唑-5-基、1,2,4-噻二唑-3-基、1,2,4-噻二唑-5-基、1,2,4-三唑-3-基、1,3,4-二唑-2-基、1,3,4-噻二唑-2-基和1,3,4-三唑-2-基;
含有1-4个氮原子的6元杂芳基:除碳原子外还可含有1-3个或1-4个氮原子作为环成员的6元杂芳基,例如2-吡啶基、3-吡啶基、4-吡啶基、3-哒嗪基、4-哒嗪基、2-嘧啶基、4-嘧啶基、5-嘧啶基、2-吡嗪基、1,3,5-三嗪-2-基和1,2,4-三嗪-3-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,其中该优选在每种情况下无论是单独还是组合均有效:
优选的环烷基部分为环戊基,其任选被一个或多个硝基、氰基、C1-C6-烷基、C1-C6-烷氧基取代。
优选的杂芳基部分是吡啶基、嘧啶基、吡唑基或噻吩基。
优选如下式I化合物:其中可以是直链或支化的基团R1或R2的任何烷基部分都含有1-9个碳原子,更优选2-6个碳原子,取代基R1或R2的任何链烯基或炔基部分都含有2-9个碳原子,更优选3-6个碳原子,取代基R1或R2的任何环烷基部分都含有3-10个碳原子,优选3-8个碳原子,更优选3-6个碳原子,以及取代基R1或R2的任何双环烷基部分都含有7-9个碳原子。任何烷基、链烯基或炔基都可以是直链或支化的。
优选其中R1不为氢的式I化合物。
此外,还优选如下式I化合物:其中R1代表直链或支化的C1-C10-烷基,尤其是支化的C3-C10-烷基,C3-C8-环烷基,C5-C9-双环烷基,C3-C8-环烷基-C1-C6-烷基,C1-C10-烷氧基-C1-C6-烷基或任选被1-3个C1-C10-烷基或C1-C10-烷氧基取代的苯基。
特别优选其中R2代表氢原子或C1-C10-烷基,尤其是氢原子的化合物I。
此外,还特别优选其中R2为甲基或乙基的化合物I。
若R1表示任选取代的C3-C8-环烷基,优选环戊基或环己基,则R2优选代表氢原子或C1-C6-烷基。
此外,还特别优选如下化合物I:其中R1和R2与其相邻氮原子一起形成任选取代的杂环,优选任选取代的C3-C7-杂环,尤其是吡咯烷、哌啶、四氢吡啶,尤其是任选被一个或多个C1-C10-烷基取代的1,2,3,6-四氢吡啶或氮杂庚环。
此外,还特别优选其中X为氯或溴,尤其是氯的化合物I。
此外,还优选其中X为氰基或甲氧基的化合物I。
此外,还特别优选其中X为乙氧基、正丙氧基、异丙氧基、烯丙氧基或3-甲基烯丙氧基的化合物I。
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也包括在本发明范围内。
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特别优选的实施方案,而与其中提到它们的组合无关。
表1
其中X为氯且R1和R2对应于表A中的一行的式I化合物
表2
其中X为溴且R1和R2对应于表A中的一行的式I化合物
表3
其中X为氰基且R1和R2对应于表A中的一行的式I化合物
表4
其中X为甲氧基且R1和R2对应于表A中的一行的式I化合物
表5
其中X为乙氧基且R1和R2对应于表A中的一行的式I化合物
表6
其中X为正丙氧基且R1和R2对应于表A中的一行的式I化合物
表7
其中X为异丙氧基且R1和R2对应于表A中的一行的式I化合物
表8
其中X为烯丙氧基且R1和R2对应于表A中的一行的式I化合物
表9
其中X为3-甲基烯丙氧基且R1和R2对应于表A中的一行的式I化合物
表A
序号 | R1 | R2 | |
A-1 | H | H | |
A-2 | CH2CH3 | H | |
A-3 | CH2CH3 | CH3 | |
A-4 | CH2CH3 | CH2CH3 | |
A-5 | CH2CH2CH3 | H | |
A-6 | CH2CH2CH3 | CH3 | |
A-7 | CH2CH2CH3 | CH2CH3 | |
A-8 | CH2CH2CH3 | CH2CH2CH3 | |
A-9 | CH(CH3)2 | H | |
A-10 | CH(CH3)2 | CH3 | |
A-11 | CH(CH3)2 | CH2CH3 | |
A-12 | (±)CH(CH3)-CH2CH3 | H | |
A-13 | (±)CH(CH3)-CH2CH3 | CH3 | |
A-14 | (±)CH(CH3)-CH2CH3 | CH2CH3 | |
A-15 | (S)CH(CH3)-CH2CH3 | H | |
A-16 | (S)CH(CH3)-CH2CH3 | CH3 | |
A-17 | (S)CH(CH3)-CH2CH3 | CH2CH3 | |
A-18 | (R)CH(CH3)-CH2CH3 | H | |
A-19 | (R)CH(CH3)-CH2CH3 | CH3 | |
A-20 | (R)CH(CH3)-CH2CH3 | CH2CH3 | |
A-21 | (±)CH(CH3)-CH(CH3)2 | H | |
A-22 | (±)CH(CH3)-CH(CH3)2 | CH3 | |
A-23 | (±)CH(CH3)-CH(CH3)2 | CH2CH3 | |
A-24 | (S)CH(CH3)-CH(CH3)2 | H | |
A-25 | (S)CH(CH3)-CH(CH3)2 | CH3 | |
A-26 | (S)CH(CH3)-CH(CH3)2 | CH2CH3 | |
A-27 | (R)CH(CH3)-CH(CH3)2 | H | |
A-28 | (R)CH(CH3)-CH(CH3)2 | CH3 | |
A-29 | (R)CH(CH3)-CH(CH3)2 | CH2CH3 | |
A-30 | (±)CH(CH3)-C(CH3)3 | H | |
A-31 | (±)CH(CH3)-C(CH3)3 | CH3 | |
A-32 | (±)CH(CH3)-C(CH3)3 | CH2CH3 | |
A-33 | (S)CH(CH3)-C(CH3)3 | H | |
A-34 | (S)CH(CH3)-C(CH3)3 | CH3 | |
A-35 | (S)CH(CH3)-C(CH3)3 | CH2CH3 | |
A-36 | (R)CH(CH3)-C(CH3)3 | H | |
A-37 | (R)CH(CH3)-C(CH3)3 | CH3 | |
A-38 | (R)CH(CH3)-C(CH3)3 | CH2CH3 |
A-39 | CH2C(CH3)=CH2 | H |
A-40 | CH2C(CH3)=CH2 | CH3 |
A-41 | CH2C(CH3)=CH2 | CH2CH3 |
A-42 | 环戊基 | H |
A-43 | 环戊基 | CH3 |
A-44 | 环戊基 | CH2CH3 |
A-45 | -(CH2)2CH(CH3)(CH2)2- |
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、叉丝单囊壳(Podosphaera)属、核盘菌(Sclerotinia)属、Physalospora canker,
·草莓、蔬菜、观赏植物和葡萄藤上的Botrytis cinerea(灰霉病),
·黄瓜上的山扁豆生棒孢(Corynespora cassiicola),
·水果和蔬菜上的刺盘孢(Colletotrichum)属,
·玫瑰上的蔷薇双壳(Diplocarpon rosae),
·柑桔类水果上的柑桔痂囊腔菌(Elsinoe fawcetti)和柑桔间座壳(Diaporthecitri),
·葫芦科植物、草莓和玫瑰上的单丝壳(Sphaerotheca)属,
·花生、糖用甜菜和茄子上的尾孢(Cercospora)属,
·葫芦科植物上的二孢白粉菌(Erysiphe cichoracearum),
·红辣椒、西红柿和茄子上的鞑靼内丝白粉菌(Leveillula taurica),
·苹果和梅上的球腔菌(Mycosphaerella)属,
·梅上的柿生球针壳(Phyllactinia kakicola)、柿盘长孢(Gloeosporiumkaki),
·苹果上的山田胶锈菌(Gymnosporangium yamadai)、仁果细盾霉(Leptothyrium pomi)、苹果白粉病菌(Podosphaera leucotricha)和仁果粘壳孢(Gloedes pomigena),
·梨和梅上的嗜果枝孢(Cladosporium carpophilum),
·梨上的拟茎点霉(Phomopsis)属,
·柑桔类水果、土豆、洋葱上的疫霉(Phytophthora)属,尤其是土豆和西红柿上的致病疫霉(Phytophthora infestans),
·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,
·茶(tee)上的围小丛壳(Glomerella cingulata),
·禾谷类和稻上的Drechslera属和Bipolaris属,
·香蕉和花生上的球腔菌(Mycosphaerella)属,
·葡萄藤上的葡萄生单轴霉(Plasmopara viticola),
·洋葱、菠菜和菊花上的霜霉(Personospora)属,
·柚子上的葡萄褐柱丝霉(Phaeoisariopsis vitis)和葡萄痂圆孢(Sphacelomaampelina),
·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,
·禾谷类和草坪上的柄锈菌(Puccinia)属和核瑚菌(Typhula)属,
·稻上的稻瘟病菌(Pyricularia oryzae),
·棉花、稻和草坪上的丝核菌(Rhizoctonia)属,
·小麦上的颖枯壳多孢(Stagonospora nodorum)和小麦壳针孢(Septoriatritici),
·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。使用形式取决于特定目的;在任何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。合适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。
下列为示例性配制剂:
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、粉末、悬浮液或分散体、乳液、油分散体、糊、粉剂、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;在任何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、增粘剂、分散剂或乳化剂将物质直接或在溶于油或溶剂之后在水中均化。另外,也可以制备由活性物质、湿润剂、增粘剂、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%,优选为0.01-1%。
活性成分还可非常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或呈其使用形式的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。
下列的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、5-氯-2-氰基-4-对甲苯基咪唑-1-磺酸二甲基酰胺、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-氯-N-(4’-氯联苯-2-基)烟酰胺、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,例如腈嘧菌酯、亚胺菌酯(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)、唑菌胺酯(pyraclostrobin)、三氟敏(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、3-(4-氟苯基)-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-唑烷、3-[3,5-二氯苯基-(5-甲基-5-甲氧基甲基)-1,3-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、3,5-二氯-N-(3-氯-1-乙基-1-甲基-2-氧代丙基)-4-甲基苯甲酰胺、1-(3-溴-6-甲氧基-2-甲基苯基)-1-(2,3,4-三甲氧基-6-甲基苯基)甲酮、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I与物理数据一起列于下表I中。
实施例1:5,7-二羟基-6-(2,6-二氟苯基)-[1,2,4]-三唑并[1,5-α]嘧啶的制备
将3-氨基-1,2,4-三唑(14g)、(2,6-二氟苯基)丙二酸二乙酯(0.17mol,参见EP-A 10 02 788)与三丁基胺(50ml)的混合物在约180℃下加热6小时。将反应混合物冷却至约70℃。加入200ml 10%氢氧化钠水溶液并将反应混合物搅拌30分钟。分离各相,将水相用乙醚萃取。酸化水相。滤出沉淀并干燥,得到40g标题化合物。
实施例2:5,7-二氯-6-(2,6-二氟苯基)-[1,2,4]-三唑并[1,5-α]嘧啶的制备
将5,7-二羟基-6-(2,6-二氟苯基)-[1,2,4]-三唑并[1,5-α]嘧啶(30g,由实施例1得到)与磷酰氯(phosphorous oxychloride,50ml)的混合物回流约8小时。部分蒸除磷酰氯。将残余物倾入二氯甲烷与水的混合物中。分离有机相,干燥并过滤。将滤液真空浓缩,得到28g标题化合物,熔点为121℃。
实施例3:5-氯-6-(2,6-二氟苯基)-7-异丙基氨基-[1,2,4]-三唑并[1,5-α]嘧啶[I-3]的制备
在搅拌下将异丙基胺(1.5mmol)、三乙基胺(1.5mmol)与二氯甲烷(10ml)的混合物加入5,7-二氯-6-(2,6-二氟苯基)-[1,2,4]-三唑并[1,5-α]嘧啶(1.5mmol,由实施例2得到)与二氯甲烷(20ml)的混合物中。将反应混合物在约20-25℃下搅拌约16小时并随后用稀盐酸(5%)洗涤。分离有机层,干燥并过滤。将滤液在减压下蒸发,并将残余物层析,得到0.43g标题化合物,熔点为169℃。
实施例4:5-氰基-6-(2,6-二氟苯基)-7-(4-甲基哌啶-1-基)-[1,2,4]-三唑并[1,5-α]嘧啶[I-18]的制备
将5-氯-6-(2,6-二氟苯基)-7-(4-甲基哌啶-1-基)-[1,2,4]-三唑并[1,5-α]嘧啶(0.1mol;I-4)和四乙基氰化铵(0.25mol)在750ml二甲基甲酰胺(DMF)(750ml)中的混合物在约20-25℃下搅拌16小时。向该混合物加入水和甲基·叔丁基醚(MTBE),分离有机相,用水洗涤,干燥并过滤。蒸发滤液并将残余物层析,得到6.95g标题化合物,熔点为212℃。
实施例5:5-甲氢基-6-(2,6-二氟苯基)-7-(二乙基氨基)-[1,2,4]-三唑并[1,5-α]嘧啶[I-19]的制备
在约20-25℃下,向5-氯-6-(2,6-二氟苯基)-7-(二乙基氨基)-[1,2,4]-三唑并[1,5-α]嘧啶(65mmol;I-6)在400ml无水甲醇中的溶液中加入30%甲醇钠溶液(71.5mmol)。将该混合物进一步搅拌16小时。蒸发甲醇并将残余物溶于二氯甲烷中。将有机相用水洗涤,干燥并过滤。蒸发滤液并将残余物层析,得到16.3g标题化合物,熔点为153℃。
表I
序号 | R1 | R2 | X | 物理数据(熔点[℃]) |
I-1 | H | H | Cl | 250 |
I-2 | CH2C(CH3)=CH2 | CH2CH3 | Cl | 96 |
I-3 | CH(CH3)2 | H | Cl | 169 |
I-4 | -(CH2)2CH(CH3)(CH2)2- | Cl | 196 | |
I-5 | 环戊基 | H | Cl | 165 |
I-6 | CH2CH3 | CH2CH3 | Cl | 159 |
I-7 | CH2CH2CH3 | CH2CH2CH3 | Cl | 125 |
I-8 | CH(CH3)2 | CH3 | Cl | 168 |
I-9 | (±)CH(CH3)-CH2CH3 | H | Cl | 184 |
I-10 | (S)CH(CH3)-CH2CH3 | H | Cl | 176 |
I-11 | (R)CH(CH3)-CH2CH3 | H | Cl | 176 |
I-12 | (±)CH(CH3)-CH(CH3)2 | H | Cl | 157 |
I-13 | (S)CH(CH3)-CH(CH3)2 | H | Cl | 149 |
I-14 | (R)CH(CH3)-CH(CH3)2 | H | Cl | 149 |
I-15 | (±)CH(CH3)-C(CH3)3 | H | Cl | 160 |
I-16 | (S)CH(CH3)-C(CH3)3 | H | Cl | 175 |
I-17 | (R)CH(CH3)-C(CH3)3 | H | Cl | 175 |
I-18 | -(CH2)2CH(CH3)(CH2)2- | CN | 212 | |
I-19 | CH2CH3 | CH2CH3 | OCH3 | 153 |
对有害真菌的作用实施例
通过下列试验证实式I化合物的杀真菌活性:
单独或一起将各活性化合物制备成在70重量%环己酮、20重量%NekanilLN(LutensolAP6,具有乳化和分散作用的湿润剂,基于乙氧基化烷基酚)和10重量%WettolEM(非离子乳化剂,基于乙氧基化蓖麻油)的混合物中的10%乳液,并用水稀释至所需浓度。
生物活性试验—对西红柿上的早疫病菌(Alternaria solani)的杀真菌防治作用
使栽培品种为“Groβe Fleischtomate St.Pierre”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,该悬浮液含有下面所述浓度的活性成分且由含有10%活性成分、85%环己酮和5%乳化剂的储备溶液制备。第二天,将处理过的植物用早疫病菌的含水悬浮液接种,该悬浮液每ml含0.2×106个孢子。然后将试验植物立即转移到潮湿室中。在20-23℃和接近100%的相对湿度下6天后,以侵染叶面积%来肉眼测定叶子上的真菌侵染程度。
在该试验中,用250ppm化合物I-2至I-9、I-11、I-12、I-14、I-15和I-17处理的植物显示出不超过1%的侵染水平,而未处理植物显示出90%的侵染水平。
使用由WO-A 98/46608已知的活性化合物A和B作为对比化合物:
序号 | 由下列文献已知 | R1 |
A | WO-A 98/46608,No.5 | 氢 |
B | WO-A 98/46608,No.7 | 甲基 |
对比试验—对青椒的果片上的灰霉病(Botrytis cinerea)的防治作用
用含水悬浮液将青椒的果片喷雾至滴流,该悬浮液含有下面所述浓度的活性成分或其混合物且由含有10%活性成分、85%环己酮和5%乳化剂的储备溶液制备。在喷雾层干燥2小时后,将圆片用含1.7×106个孢子/ml的灰霉病病菌在2重量%生物麦芽水溶液中的孢子悬浮液接种。然后将侵染的果片在18-20℃和高湿度的室中培养4天。然后,以%肉眼测定真菌侵染的果片面积。
在该试验中,分别用500ppm化合物I-2、I-8和I-14处理的植物显示出不超过3%的侵染水平,而分别用500ppm对比化合物A和B处理的植物显示出的侵染水平分别为100%和20%,未处理植物的侵染水平为100%。
Claims (6)
1.式I的6-(2,6-二氟苯基)三唑并嘧啶:
其中
R1为直链或支化的C1-C6-烷基、C2-C6-链烯基或C3-C9-环烷基,和
R2为氢或C1-C6-烷基,或
R1和R2与其相邻氮原子一起代表具有5或6个碳原子且任选被1或2个C1-C6-烷基取代的杂环;
X为卤素、氰基、C1-C6-烷氧基、C1-C6-卤代烷氧基或C3-C8-链烯氧基。
2.根据权利要求1的化合物,其中R2为氢。
3.根据权利要求1或2的化合物,其中X为卤素。
5.一种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。
6.一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化合物处理真菌或要防止真菌侵染的材料、植物、土壤或种子。
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HU (1) | HUP0401048A3 (zh) |
IL (1) | IL159605A0 (zh) |
MX (1) | MXPA04000044A (zh) |
NZ (1) | NZ531066A (zh) |
PL (1) | PL367615A1 (zh) |
WO (1) | WO2003008415A1 (zh) |
ZA (1) | ZA200401255B (zh) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE10218592A1 (de) * | 2002-04-26 | 2003-11-06 | Bayer Cropscience Ag | Triazolopyrimidine |
CA2520718A1 (en) * | 2003-04-02 | 2004-10-14 | Basf Aktiengesellschaft | 7-alkinylamino-triazolopyrimidines, methods for the production and use thereof to combat harmful fungi and agents containing said compounds |
WO2005058900A1 (de) * | 2003-11-25 | 2005-06-30 | Basf Aktiengesellschaft | 6-(2,4,6-trifluorphenyl)-triazolopyrimidine, verfahren zu ihrer hestellung und ihre verwendung zur bekämpfung von schadpilzen sowie sie enthaltende mittel |
WO2005058903A1 (de) * | 2003-12-17 | 2005-06-30 | Basf Aktiengesellschaft | 6-(2,4,6-trihalogenphenyl)-triazolopyrimidine, verfahren zu ihrer herstellung und ihre verwendung zur bekämpfung von schadpilzen sowie sie enthaltende mittel |
WO2005095404A2 (de) * | 2004-03-30 | 2005-10-13 | Basf Aktiengesellschaft | 6-(2-fluorphenyl)-triazolopyrimidine, verfahren zu ihrer herstellung und ihre verwendung zur bekämpfung von schadpilzen sowie sie enthaltende mittel |
EP1952691A3 (en) * | 2007-01-31 | 2008-09-17 | Basf Se | Method for improving plant health by application of a triazolopyrimidine derivative |
Citations (2)
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CN1257502A (zh) * | 1997-04-14 | 2000-06-21 | 美国氰胺公司 | 杀真菌剂三氟甲基烷氨基三唑并嘧啶 |
CN1302299A (zh) * | 1998-03-23 | 2001-07-04 | 美国氰胺公司 | 杀真菌的6-(2-卤代-4-烷氧基苯基)-三唑并嘧啶 |
Family Cites Families (11)
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DE3130633A1 (de) * | 1981-08-01 | 1983-02-17 | Basf Ag, 6700 Ludwigshafen | 7-amino-azolo(1,5-a)pyrimidine und diese enthaltende fungizide |
TW224044B (zh) * | 1991-12-30 | 1994-05-21 | Shell Internat Res Schappej B V | |
US5593996A (en) * | 1991-12-30 | 1997-01-14 | American Cyanamid Company | Triazolopyrimidine derivatives |
US5817663A (en) * | 1996-10-07 | 1998-10-06 | American Cyanamid Company | Pentafluorophenylazolopyrimidines |
US5948783A (en) * | 1997-04-14 | 1999-09-07 | American Cyanamid Company | Fungicidal trifluoromethylalkylamino-triazolopyrimidines |
TWI252231B (en) * | 1997-04-14 | 2006-04-01 | American Cyanamid Co | Fungicidal trifluorophenyl-triazolopyrimidines |
US5994360A (en) * | 1997-07-14 | 1999-11-30 | American Cyanamid Company | Fungicidal 5-alkyl-triazolopyrimidines |
US6117865A (en) * | 1998-09-10 | 2000-09-12 | American Cyanamid Company | Fungicidal trifluorophenyl-triazolopyrimidines |
US6277856B1 (en) * | 1998-09-25 | 2001-08-21 | American Cynamid Co. | Fungicidal mixtures |
US5986135A (en) * | 1998-09-25 | 1999-11-16 | American Cyanamid Company | Fungicidal trifluoromethylalkylamino-triazolopyrimidines |
ATE274518T1 (de) * | 2001-04-11 | 2004-09-15 | Basf Ag | 6-(2-chlor-6-fluor-phenyl)-triazolpyrimidine |
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2002
- 2002-07-08 IL IL15960502A patent/IL159605A0/xx unknown
- 2002-07-08 MX MXPA04000044A patent/MXPA04000044A/es active IP Right Grant
- 2002-07-08 US US10/483,597 patent/US20040162428A1/en not_active Abandoned
- 2002-07-08 JP JP2003513974A patent/JP2005500334A/ja not_active Withdrawn
- 2002-07-08 KR KR10-2004-7000705A patent/KR20040015816A/ko not_active Application Discontinuation
- 2002-07-08 CA CA002453638A patent/CA2453638A1/en not_active Abandoned
- 2002-07-08 NZ NZ531066A patent/NZ531066A/en unknown
- 2002-07-08 HU HU0401048A patent/HUP0401048A3/hu unknown
- 2002-07-08 BR BR0211179-9A patent/BR0211179A/pt not_active IP Right Cessation
- 2002-07-08 PL PL02367615A patent/PL367615A1/xx not_active Application Discontinuation
- 2002-07-08 CN CNB028144112A patent/CN1313467C/zh not_active Expired - Fee Related
- 2002-07-08 EA EA200400106A patent/EA007150B1/ru not_active IP Right Cessation
- 2002-07-08 WO PCT/EP2002/007575 patent/WO2003008415A1/en not_active Application Discontinuation
- 2002-07-08 EP EP02751120A patent/EP1412358A1/en not_active Withdrawn
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Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
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CN1257502A (zh) * | 1997-04-14 | 2000-06-21 | 美国氰胺公司 | 杀真菌剂三氟甲基烷氨基三唑并嘧啶 |
CN1302299A (zh) * | 1998-03-23 | 2001-07-04 | 美国氰胺公司 | 杀真菌的6-(2-卤代-4-烷氧基苯基)-三唑并嘧啶 |
Also Published As
Publication number | Publication date |
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EA007150B1 (ru) | 2006-08-25 |
HUP0401048A2 (hu) | 2004-09-28 |
PL367615A1 (en) | 2005-03-07 |
ZA200401255B (en) | 2005-03-10 |
BR0211179A (pt) | 2004-10-19 |
CN1533394A (zh) | 2004-09-29 |
EP1412358A1 (en) | 2004-04-28 |
WO2003008415A1 (en) | 2003-01-30 |
JP2005500334A (ja) | 2005-01-06 |
US20040162428A1 (en) | 2004-08-19 |
CA2453638A1 (en) | 2003-01-30 |
KR20040015816A (ko) | 2004-02-19 |
NZ531066A (en) | 2005-04-29 |
IL159605A0 (en) | 2004-06-01 |
EA200400106A1 (ru) | 2004-06-24 |
HUP0401048A3 (en) | 2007-02-28 |
MXPA04000044A (es) | 2004-05-21 |
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