CN101568259A - 唑基甲基环氧乙烷、其在防治植物病原性真菌中的用途以及包含它们的组合物 - Google Patents
唑基甲基环氧乙烷、其在防治植物病原性真菌中的用途以及包含它们的组合物 Download PDFInfo
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- CN101568259A CN101568259A CNA2007800478505A CN200780047850A CN101568259A CN 101568259 A CN101568259 A CN 101568259A CN A2007800478505 A CNA2007800478505 A CN A2007800478505A CN 200780047850 A CN200780047850 A CN 200780047850A CN 101568259 A CN101568259 A CN 101568259A
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- 239000002243 precursor Substances 0.000 description 1
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- WHMZYGMQWIBNOC-UHFFFAOYSA-N propan-2-yl n-(3,4-dimethoxyphenyl)carbamate Chemical compound COC1=CC=C(NC(=O)OC(C)C)C=C1OC WHMZYGMQWIBNOC-UHFFFAOYSA-N 0.000 description 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- 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
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- PUYXTUJWRLOUCW-UHFFFAOYSA-N spiroxamine Chemical compound O1C(CN(CC)CCC)COC11CCC(C(C)(C)C)CC1 PUYXTUJWRLOUCW-UHFFFAOYSA-N 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
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- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
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- 239000004094 surface-active agent Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- IWVCMVBTMGNXQD-UHFFFAOYSA-N terramycin dehydrate Natural products C1=CC=C2C(O)(C)C3C(O)C4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 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
- OBZIQQJJIKNWNO-UHFFFAOYSA-N tolclofos-methyl Chemical compound COP(=S)(OC)OC1=C(Cl)C=C(C)C=C1Cl OBZIQQJJIKNWNO-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 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
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- JARYYMUOCXVXNK-CSLFJTBJSA-N validamycin A Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-CSLFJTBJSA-N 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- FJBGIXKIXPUXBY-UHFFFAOYSA-N {2-[3-(4-chlorophenyl)propyl]-2,4,4-trimethyl-1,3-oxazolidin-3-yl}(imidazol-1-yl)methanone Chemical compound C1=CN=CN1C(=O)N1C(C)(C)COC1(C)CCCC1=CC=C(Cl)C=C1 FJBGIXKIXPUXBY-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
Abstract
本发明涉及通式(I)的唑基甲基环氧乙烷,其中A为任选被1-3个下列取代基取代的苯基:卤素、NO2、氨基、C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷基、C1-C4卤代烷氧基、C1-C4烷基氨基、C1-C4二烷基氨基、硫代或C1-C4烷硫基,条件是A不为2-甲基苯基;涉及其植物相容性酸加成盐或金属盐以及式I化合物在防治植物病原性真菌中的用途和包含这些化合物的组合物。
Description
本发明涉及通式I的唑基甲基环氧乙烷及其植物相容性酸加成盐或金属盐:
其中
A为任选被1-3个下列取代基取代的苯基:卤素、NO2、氨基、C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷基、C1-C4卤代烷氧基、C1-C4烷基氨基、C1-C4二烷基氨基、硫代或C1-C4烷硫基,条件是A不为2-甲基苯基。
此外,本发明涉及式I化合物在防治植物病原性真菌中的用途以及包含这些化合物的组合物。
唑基甲基环氧乙烷、其制备及其在作物保护中的用途例如由EP-A 0094 564和EP-A 0 196 038已知。
在环氧乙烷环上带有杂芳基取代基的唑基甲基环氧乙烷由EP-A 0 421125已知。
所述唑基甲基环氧乙烷对许多病原体具有良好至非常良好的杀真菌活性;然而,本发明的目的是提供具有改进杀真菌活性的新型唑基甲基环氧乙烷。
该目的由开头所述的式I化合物实现。
由于其氮原子的碱性特性,化合物I能够与无机或有机酸或与金属离子形成盐或加合物。
无机酸的实例是氢卤酸如氟化氢、氯化氢、溴化氢和碘化氢,碳酸,硫酸,磷酸和硝酸。
合适的有机酸例如为甲酸和链烷酸,如乙酸、三氟乙酸、三氯乙酸和丙酸,还有乙醇酸、硫氰酸、乳酸、琥珀酸、柠檬酸、苯甲酸、肉桂酸、草酸、烷基磺酸(具有1-20个碳原子的直链或支化烷基的磺酸)、芳基磺酸或芳基二磺酸(带有1或2个磺酸基团的芳基,如苯基和萘基)、烷基膦酸(具有1-20个碳原子的直链或支化烷基的膦酸)、芳基膦酸或芳基二膦酸(带有1或2个磷酸基团的芳基,如苯基和萘基),其中烷基或芳基可以带有其他取代基,例如对甲苯磺酸、水杨酸、对氨基水杨酸、2-苯氧基苯甲酸、2-乙酰氧基苯甲酸等。
合适的金属离子尤其是第二主族元素的离子,特别是钙和镁离子,第三和第四主族元素的离子,特别是铝、锡和铅离子,以及第一至第八过渡族元素的离子,特别是铬、锰、铁、钴、镍、铜、锌和其他离子。特别优选第四过渡族元素的金属离子。金属可以可能的各种价态存在。
式I化合物的制备是已知的且详细描述于EP-A 0 094 564、EP-A 0 196038和EP-A 0 421 125中。
在上式所给符号的定义中,使用通常为下列取代基的代表的集合性术语:
卤素:氟、氯、溴和碘。
烷基以及复合基团如烷基氨基的烷基结构部分:优选具有1-4个碳原子的饱和直链或支化烃基,如甲基、乙基、丙基、1-甲基乙基、丁基、1-甲基丙基、2-甲基丙基和1,1-二甲基乙基。
卤代烷基,如上所提到的烷基,其中这些基团中的部分或所有氢原子被上述卤原子替换。在一个实施方案中,烷基至少被特定卤原子,优选氟、氯或溴取代一次或完全取代。在另一实施方案中,烷基被不同卤原子部分或完全卤代;在混合卤素取代的情况下,优选氯和氟的组合。特别优选C1-C4卤代烷基,更优选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、五氟乙基或1,1,1-三氟丙-2-基。
烷氧基:经由氧连接的如上所定义的烷基,优选具有1-4个碳原子。优选烷氧基的实例是甲氧基、乙氧基、正丙氧基、1-甲基乙氧基、丁氧基、1-甲基丙氧基、2-甲基丙氧基或1,1-二甲基乙氧基。
卤代烷氧基:如上所定义的烷氧基,其中这些基团中的部分或全部氢原子被在卤代烷基下所述的卤原子,尤其是氟、氯或溴替换。优选的卤代烷氧基实例是OCH2F、OCHF2、OCF3、OCH2Cl、OCHCl2、OCCl3、氯氟甲氧基、二氯一氟甲氧基、一氯二氟甲氧基、2-氟乙氧基、2-氯乙氧基、2-溴乙氧基、2-碘乙氧基、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、OC2F5、2-氟丙氧基、3-氟丙氧基、2,2-二氟丙氧基、2,3-二氟丙氧基、2-氯丙氧基、3-氯丙氧基、2,3-二氯丙氧基、2-溴丙氧基、3-溴丙氧基、3,3,3-三氟丙氧基、3,3,3-三氯丙氧基、OCH2-C2F5、OCF2-C2F5、1-(CH2F)-2-氟乙氧基、1-(CH2Cl)-2-氯乙氧基、1-(CH2Br)-2-溴乙氧基、4-氟丁氧基、4-氯丁氧基、4-溴丁氧基或九氟丁氧基。
烷硫基:经由硫原子连接的如上所定义的烷基。
新的式I化合物含有手性中心且通常以外消旋体形式或赤型和苏型的非对映体混合物得到。本发明化合物的赤型和苏型非对映体可以例如基于它们的不同溶解度或通过柱层析以纯净形式分离和离析。使用已知方法可以将这类均匀的非对映体对用于得到均匀的对映体。对于用作抗菌剂合适的是在合成中得到的均匀非对映体或对映体及其混合物。这相应地用于杀真菌组合物。
本发明化合物可以生物活性可能不同的各种晶型存在。它们同样由本发明提供。
在本发明的式I化合物或根据本发明使用的式I化合物中,特别优选下列取代基含义,在每种情况下单独或组合。这里优选的取代基或优选的取代基组合合适的话相应地用于本发明化合物的前体。
取代基A为任选被1-3个下列取代基取代的苯基:卤素、NO2、氨基、C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷基、C1-C4卤代烷氧基、C1-C4烷基氨基、C1-C4二烷基氨基、硫代或C1-C4烷硫基。
在另一实施方案中,取代基A为被1-3个下列取代基取代的苯基:卤素、C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷基或C1-C4卤代烷氧基。
在优选实施方案中,取代基A为被1-3个卤素取代的苯基。
尤其考虑到它们的用途,优选汇编在下表1中的化合物I。此外,对表中取代基所提到的基团本身为所述取代基的特别优选实施方案。
表1:
化合物 | 取代基A |
1-1 | 3-甲基苯基 |
1-2 | 4-甲基苯基 |
1-3 | 2-甲氧基苯基 |
1-4 | 3-甲氧基苯基 |
1-5 | 4-甲氧基苯基 |
1-6 | 2-氯苯基 |
1-7 | 3-氯苯基 |
1-8 | 4-氯苯基 |
1-9 | 2-氟苯基 |
1-10 | 3-氟苯基 |
1-11 | 4-氟苯基 |
1-12 | 2-氯-3-甲氧基苯基 |
1-13 | 2-氯-4-甲氧基苯基 |
1-14 | 2,3-二氯苯基 |
1-15 | 2,4-二氯苯基 |
1-16 | 3,4-二氯苯基 |
1-17 | 2,3-二氟苯基 |
1-18 | 2,4-二氟苯基 |
1-19 | 2-氯-3-氟苯基 |
1-20 | 2-氯-4-氟苯基 |
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优异的活性,所述真菌尤其选自子囊菌纲(Ascomycetes)、半知菌纲(Deuteromycetes)、卵菌纲(Oomycetes)和担子菌纲(Basidiomycetes)真菌,尤其是卵菌纲。它们中的一些内吸有效并可以作为叶面杀真菌剂、拌种用杀真菌剂和土壤杀真菌剂用于作物保护中。
它们对在各种作物植株如小麦、黑麦、大麦、黑小麦、燕麦、稻、玉米、禾草、香蕉、棉花、大豆、咖啡、甘蔗、葡萄藤、水果和观赏植物以及蔬菜如黄瓜、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。它们还可以用于由于包括基因工程方法在内的育种而耐受昆虫或真菌侵袭或耐受除草剂施用的作物。此外,它们适于防治尤其侵袭木材或葡萄藤的根的葡萄座腔菌属(Botryosphaeria)、柱孢属(Cylindrocarpon)、葡萄顶枯病菌(Eutypa lata)、Neonectria liriodendri和毛韧革菌(Stereum hirsutum)。
它们尤其适于防治下列植物病害:
●蔬菜、油籽油菜、糖用甜菜、水果和稻上的链格孢属(Alternaria),例如土豆和西红柿上的早疫链格孢(A.solani)或链格孢(A.alternata);
●糖用甜菜和蔬菜上的丝囊霉属(Aphanomyces);
●禾谷类和蔬菜上的壳二孢属(Ascochyta);
●玉米、禾谷类、稻和草坪中的平脐蠕孢属(Bipolaris)和内脐蠕孢属(Drechslera),例如玉米上的玉蜀黍平脐蠕孢(D.maydis);
●禾谷类上的禾白粉菌(Blumeria graminis)(白粉病);
●草莓、蔬菜、花卉和葡萄藤上的灰葡萄孢(Botrytis cinerea)(灰霉病),
●莴苣上的莴苣盘梗霉(Bremia lactucae),
●玉米、大豆、稻和糖用甜菜上的尾孢属(Cercospora);
●玉米、禾谷类、稻上的旋孢腔菌属(Cochliobolus),例如禾谷类上的禾旋孢腔菌(Cochliobolus sativus),稻上的宫部旋孢腔菌(Cochliobolusmiyab eanus);
●大豆和棉花上的剌盘孢属(Colletotricum);
●玉米、禾谷类、稻和草坪上的内脐蠕孢属(Drechslera)、核腔菌属(Pyrenophora),例如大麦上的大麦网斑内脐蠕孢(D.teres)或小麦上的D.tritci-repentis;
●由Phaeoacremonium chlamydosporium、Ph.Aleophilum和Formitiporapunctata(同义词斑孔木层孔菌(Phellinus punctatus))引起的葡萄藤上的埃斯卡(Esca);
●玉米上的突脐蠕孢属(Exserohilum),
●黄瓜上的二孢白粉菌(Erysiphe cichoracearum)和单丝壳白粉菌(Sphaerotheca fuliginea),
●各种植物上的镰孢霉属(Fusarium)和轮枝孢属(Verticillium),例如禾谷类上的禾本科镰孢(F.graminearum)或大刀镰孢(F.culmorum)或多种植物如西红柿上的尖镰孢(F.oxysporum);
●禾谷类上的禾顶囊壳(Gaeumanomyces graminis);
●禾谷类和稻上的赤霉属(Gibberella)(例如稻上的藤仓赤霉(Gibberellafujikuroi));
●稻上的Grainstaining complex;
●玉米和稻上的长蠕孢属(Helminthosporium);
●禾谷类上的Michrodochium nivale;
●禾谷类、香蕉和花生上的球腔菌属(Mycosphaerella),例如小麦上的禾生球腔菌(M.graminicola)或香蕉上的斐济球腔菌(M.fijiensis);
●卷心菜和球茎植物上的霜霉属(Peronospora),例如卷心菜上的芸苔霜霉(P.brassicae)或洋葱上的大葱霜霉(P.destructor);
●大豆上的豆薯层锈菌(Phakopsora pachyrhizi)和山马蟥层锈菌(Phakopsara meibomiae);
●大豆和向日葵上的拟茎点霉属(Phomopsis);
●土豆和西红柿上的致病疫霉(Phytophthora infestans);
●各种植物上的疫霉属(Phytophthora),例如柿子椒上的辣椒疫霉(P.capsici);
●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),
●禾谷类上的小麦基腐病菌(Pseudocercosporella herpotrichoides),
●各种植物上的假霜霉属(Pseudoperonospora),例如黄瓜上的古巴假霜霉(P.cubensis)或啤酒花上的葎草假霜(P.humili);
●各种植物上的柄锈菌属(Puccinia),例如禾谷类上的小麦柄锈菌(P.triticina)、条形柄锈病(P.striformis)、大麦柄锈病(P.hordei)或禾柄锈菌(P.graminis),或芦笋上的天门冬属柄锈病(P.asparagi));
●稻上的稻瘟病菌(Pyricularia oryzae)、笹木伏革菌(Corticium sasakii)、帚梗柱孢属(Sarocladium oryzae)、稻叶鞘腐败病(S.attenuatum)、稻叶黑粉菌(Entyloma oryzae),
●草坪和禾谷类上的稻梨孢菌(Pyricularia grisea),
●草坪、稻、玉米、棉花、油籽油菜、向日葵、糖用甜菜、蔬菜和其他植物上的腐霉属(Pythium),例如各种植物上的终极腐霉菌(P.ultiumum),草坪上的瓜果腐霉(P.aphanidermatum);
●棉花、稻、土豆、草坪、玉米、油籽油菜、糖用甜菜、蔬菜和各种植物上的丝核菌属(Rhizoctonia),例如甜菜和各种植物上的立枯丝核病菌(R.solani);
●大麦、黑麦和黑小麦上的黑麦喙孢(Rhynchosporium secalis);
●油籽油菜和向日葵上的核盘菌属(Sclerotinia);
●小麦上的小麦壳针孢(Septoria tritici)和颖枯壳多孢(Stagonosporanodorum),
●葡萄藤上的葡萄钩丝壳(Erysiphe(同义词Uncinula)necator),
●玉米和草坪上的Setospaeria属,
●玉米上的丝轴黑粉菌(Sphacelotheca reilinia),
●大豆和棉花上的根串珠霉属(Thievaliopsis),
●禾谷类上的腥黑粉菌属(Tilletia),
●禾谷类、玉米和甘蔗上的黑粉菌属(Ustilago),例如玉米上的玉蜀黍黑粉菌(U.maydis);
●苹果和梨上的黑星菌属(Venturia)(黑星病),例如苹果上的苹果黑星病(V.inaequalis)。
它们特别适于防治选自Peronosporomycetes(同义词:卵菌纲),如霜霉属、疫霉属、葡萄生单轴霉、假霜霉属和腐霉属的有害真菌。
化合物I还适于防治有害真菌以保护材料(如木材、纸张、漆分散体、纤维或织物)和保护储藏的产品。在木材保护中,特别应注意下列有害真菌:子囊菌纲真菌,如线嘴壳属(Ophiostoma spp.),长喙壳属(Ceratocystisspp.),出芽短梗霉(Aureobasidium pullulans),Sclerophoma spp.,毛壳属(Chaetomium spp.),腐质霉属(Humicola spp.),彼得壳属(Petriella spp.),毛束霉属(Trichurus spp.);担子菌纲真菌,如粉孢革菌属(Coniophoraspp.),革盖菌属(Coriolus spp.),粘褶菌属(Gloeophyllum spp.),香菇属(Lentinus spp.),侧耳属(Pleurotus spp.),卧孔菌属(Poria spp.),干朽菌属(Serpula spp.)和干酪菌属(Tyromyces spp.),半知菌纲真菌,如曲霉属(Aspergillus spp.),枝孢属(Cladosporium spp.),青霉属(Penicillium spp.),木霉属(Trichoderma spp.),链格孢属(Alternaria spp.),拟青霉属(Paecilomyces spp.)和接合菌纲(Zygomycetes)真菌,如毛霉属(Mucor spp.),此外在材料保护中应注意下列酵母:假丝酵母属(Candida spp.)和酿酒酵母(Saccharomyces cerevisae)。
化合物I通过用杀真菌有效量的活性化合物处理真菌或需要防止真菌侵袭的植物、种子或材料或土壤而使用。施用可以在材料、植物或种子被真菌侵染之前和之后进行。
杀真菌组合物通常包含0.1-95重量%,优选0.5-90重量%的活性化合物。
当用于作物保护时,施用率取决于所需效果的种类为0.01-2.0kg活性化合物/公顷。
在种子处理中,每100kg种子通常要求的活性化合物量为1-1000g,优选5-100g。
当用于保护材料或储存产品时,活性化合物的施用率取决于施用区域的类型和所需效果。在材料保护中通常施用的量例如每m3处理材料为0.001g-2kg,优选0.005g-1kg活性化合物。
式I化合物可以生物活性可能不同的各种晶型存在。它们同样为本发明的主题。
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、糊和颗粒。施用形式取决于特定的目的;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,例如通过将活性化合物与溶剂和/或载体混合而制备,若需要的话使用乳化剂和分散剂。适于该目的的溶剂/助剂主要为:-水、芳族溶剂(如Solvesso产品、二甲苯)、石蜡(如矿物油馏分)、醇类(如甲醇、丁醇、戊醇、苄醇)、酮类(如环己酮、γ-丁内酯)、吡咯烷酮(NMP、NOP)、乙酸酯(乙二醇二乙酸酯)、二元醇、脂肪酸二甲基酰胺、脂肪酸及脂肪酸酯。原则上还可以使用溶剂混合物。
-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(如细碎的硅石、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。
适于用作表面活性剂的是木素磺酸、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,脂肪酸和硫酸化脂肪醇乙二醇醚,还有磺化萘与甲醛的缩合物和萘衍生物与甲醛的缩合物,萘或萘磺酸与苯酚和甲醛的缩合物,聚氧乙烯辛基苯基醚,乙氧基化异辛基酚、辛基酚、壬基酚,烷基苯基聚乙二醇醚,三丁基苯基聚乙二醇醚,三硬脂基苯基聚乙二醇醚,烷基芳基聚醚醇,醇和脂肪醇/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。
适于制备可直接喷雾溶液、乳液、糊或油分散体的物质是中至高沸点的矿物油馏分如煤油或柴油,还有煤焦油和植物或动物来源的油,脂族、环状和芳族烃如甲苯、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,环己醇,环己酮,异佛尔酮,强极性溶剂如二甲亚砜、N-甲基吡咯烷酮和水。
粉末、撒播材料和可撒粉产品可以通过将活性物质与固体载体混合或一起研磨来制备。
颗粒如涂覆颗粒、浸渍颗粒和均质颗粒可以通过使活性化合物与固体载体粘附而制备。固体载体的实例为矿土如硅胶、硅酸盐、滑石、高岭土、活性粘土(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、脲以及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。
配制剂通常包含0.01-95重量%,优选0.1-90重量%的活性化合物。活性化合物以90-100%,优选95-100%的纯度(根据NMR谱)使用。
下列为配制剂实例:
1.用水稀释的产品
A)水溶性浓缩物(SL、LS)
将10重量份活性化合物溶于90重量份水或水溶性溶剂中。或者,加入湿润剂或其它助剂。活性化合物经水稀释溶解。得到活性化合物含量为10重量%的配制剂。
B)分散性浓缩物(DC)
将20重量份活性化合物溶于70重量份环己酮中并加入10重量份分散剂如聚乙烯基吡咯烷酮。用水稀释得到分散体。活性化合物含量为20重量%。
C)乳油(EC)
将15重量份活性化合物溶于75重量份二甲苯中并加入十二烷基苯磺酸钙和蓖麻油乙氧基化物(在每种情况下为5重量份)。用水稀释得到乳液。该配制剂的活性化合物含量为15重量%。
D)乳液(EW、EO、ES)
将25重量份活性化合物溶于35重量份二甲苯中并加入十二烷基苯磺酸钙和蓖麻油乙氧基化物(在每种情况下为5重量份)。借助乳化机(例如Ultraturrax)将该混合物加入30重量份水中并制成均相乳液。用水稀释得到乳液。该配制剂的活性化合物含量为25重量%。
E)悬浮液(SC、OD、FS)
在搅拌的球磨机中,将20重量份活性化合物粉碎并加入10重量份分散剂和湿润剂以及70重量份水或有机溶剂,得到细碎活性化合物悬浮液。用水稀释得到稳定的活性化合物悬浮液。该配制剂中的活性化合物含量为20重量%。
F)水分散性颗粒和水溶性颗粒(WG、SG)
将50重量份活性化合物细碎研磨并加入50重量份分散剂和湿润剂,借助工业装置(如挤出机、喷雾塔、流化床)将其制成水分散性或水溶性颗粒。用水稀释得到稳定的活性化合物分散体或溶液。该配制剂的活性化合物含量为50重量%。
G)水分散性粉末和水溶性粉末(WP、SP、SS、WS)
将75重量份活性化合物在转子-定子磨机中研磨并加入25重量份分散剂、湿润剂和硅胶。用水稀释得到稳定的活性化合物分散体或溶液。该配制剂的活性化合物含量为75重量%。
H)凝胶配制剂(GF)
在球磨机中将20重量份活性化合物、10重量份分散剂、1重量份胶凝剂和70重量份水或有机溶剂研磨得到微细悬浮液。用水稀释得到活性化合物含量为20重量%的稳定悬浮液。
2.不经稀释而施用的产品
I)粉剂(DP、DS)
将5重量份活性化合物细碎研磨并与95重量份细碎高岭土充分混合。这得到活性化合物含量为5重量%的可撒粉产品。
J)颗粒(GR、FG、GG、MG)
将0.5重量份活性化合物细碎研磨并结合99.5重量份载体。现行方法是挤出、喷雾干燥或流化床方法。这得到不经稀释而施用的活性化合物含量为0.5重量%的颗粒。
K)ULV溶液(UL)
将10重量份活性化合物溶于90重量份有机溶剂如二甲苯中。这得到不经稀释而施用的活性化合物含量为10重量%的产品。
对于种子处理,通常使用水溶性浓缩物(LS)、悬浮液(FS)、粉剂(DS)、水分散性和水溶性粉末(WS、SS)、乳液(ES)、乳油(EC)和凝胶配制剂(GF)。这些配制剂可以未经稀释或优选稀释的形式施用于种子上。施用可以在播种前进行。
活性化合物可以直接、以其配制剂形式或由其制备的使用形式(如可直接喷雾溶液、粉末、悬浮液或分散体、乳液、油分散体、糊、可撒粉产品、撒播用材料或颗粒),借助喷雾、雾化、撒粉、撒播或浇灌来使用。使用形式完全取决于意欲的目的;意欲在每种情况下确保本发明活性化合物的最佳可能分布。
含水使用形式可通过加入水由乳液浓缩物、糊或可湿性粉末(可喷雾粉末、油分散体)制备。为制备乳液、糊或油分散体,可借助湿润剂、增粘剂、分散剂或乳化剂将该物质直接或溶于油或溶剂中后在水中均化。或者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浓缩物适于用水稀释。
活性化合物在即用制剂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%。
活性化合物还可成功地以超低容量法(ULV)使用,其中可以施用包含超过95重量%活性化合物的配制剂或甚至可以在没有添加剂的情况下施用活性化合物。
可以向活性化合物中加入各种类型的油、润湿剂、辅助剂、除草剂、杀真菌剂、其他农药或杀菌剂,合适的话恰在紧临使用之前加入(桶混合)。这些组合物通常以1∶100-100∶1,优选1∶10-10∶1的重量比与本发明组合物混合。
就此而言适合作为辅助剂的尤其为下列:有机改性的聚硅氧烷,例如Break Thru S醇烷氧基化物,例如AtplusAtplus MBAPlurafac LF和Lutensol ONEO/PO嵌段聚合物,例如PluronieRPE和Genapol醇乙氧基化物,例如Lutensol XP以及磺基琥珀酸二辛酯钠,例如Leophen
本发明组合物还可以杀真菌剂的施用形式与其它活性化合物一起存在,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。当将化合物I或包含它们的组合物与一种或多种其它活性化合物,尤其是杀真菌剂混合时,在许多情况下例如可以拓宽活性谱或防止产生抗药性。在许多情况下得到协同增效作用。
此外,本发明提供了至少一种式I的唑基甲基环氧乙烷,尤其是本说明书中作为优选公开的唑基甲基环氧乙烷,和/或其可农用盐和至少一种其他杀真菌、杀虫、除草和/或生长调节活性化合物的组合,可以存在协同增效作用。
本发明还提供了一种农药组合物,包含至少一种式I化合物,尤其是在本说明书中作为优选描述的式I化合物,和/或其可农用酸加成盐或金属盐和至少一种固体或液体载体。该农药组合物可以包含至少一种其他杀真菌、杀虫和/或除草活性化合物,还可以存在协同增效作用。
可以与本发明化合物一起施用的下列杀真菌剂L用来说明可能的组合但不限制它们:
列举L:
嗜球果伞素类(Strobilurins)
-腈嘧菌酯(azoxystrobin)、醚菌胺(dimoxystrobin)、烯肟菌酯(enestroburin)、氟嘧菌酯(fluoxastrobin)、亚胺菌(kresoxim-methyl)、叉氨苯酰胺(metominostrobin)、肟醚菌胺(orysastrobin)、啶氧菌酯(picoxystrobin)、唑菌胺酯(pyraclostrobin)、pyribencarb、肟菌酯(trifloxystrobin)、2-(2-(6-(3-氯-2-甲基苯氧基)-5-氟嘧啶-4-基氧基)苯基)-2-甲氧亚氨基-N-甲基乙酰胺、2-(邻-((2,5-二甲基苯氧基亚甲基)苯基)-3-甲氧基丙烯酸甲酯、3-甲氧基-2-(2-(N-(4-甲氧基苯基)环丙烷甲亚胺酰基硫基甲基)苯基)丙烯酸甲酯;
羧酰胺类
-羧酰苯胺类:苯霜灵(benalaxyl)、精苯霜灵(benalaxyl-M)、麦锈灵(benodanil)、bixafen、啶酰菌胺(boscalid)、萎锈灵(carboxin)、呋菌胺(fenfuram)、环酰菌胺(fenhexamid)、氟酰胺(flutolanil)、呋吡唑灵(furametpyr)、异噻菌胺(isotianil)、kiralaxyl、丙氧灭绣胺(mepronil)、甲霜灵(metalaxyl)、甲呋酰胺(ofurace)、噁霜灵(oxadixyl)、氧化萎锈灵(oxycarboxin)、吡噻菌胺(penthiopyrad)、叶枯酞(tecloftalam)、溴氟唑菌(thifluzamide)、噻酰菌胺(tiadinil)、2-氨基-4-甲基噻唑-5-甲酰苯胺、2-氯-N-(1,1,3-三甲基茚满-4-基)烟酰胺、N-(3′,4′-二氯-5-氟联苯-2-基)-3-二氟甲基-1-甲基-1H-吡唑-4-甲酰胺、N-[2-(1,3-二甲基丁基)苯基]-5-氟-1,3-二甲基-1H-吡唑-4-甲酰胺、N-(4′-氯-3′,5-二氟联苯-2-基)-3-二氟甲基-1-甲基-1H-吡唑-4-甲酰胺、N-(4′-氯-3′,5-二氟联苯-2-基)-3-三氟甲基-1-甲基-1H-吡唑-4-甲酰胺、N-(3′,4′-二氯-5-氟联苯-2-基)-3-三氟甲基-1-甲基-1H-吡唑-4-甲酰胺、N-(3′,5-二氟-4′-甲基联苯-2-基)-3-二氟甲基-1-甲基-1H-吡唑-4-甲酰胺、N-(3′,5-二氟-4′-甲基联苯-2-基)-3-三氟甲基-1-甲基-1H-吡唑-4-甲酰胺、N-(2-双环丙-2-基苯基)-3-二氟甲基-1-甲基-1H-吡唑-4-甲酰胺、N-(顺式-2-双环丙-2-基苯基)-3-二氟甲基-1-甲基-1H-比唑-4-甲酰胺、N-(反式-2-双环丙-2-基苯基)-3-二氟甲基-1-甲基-1H-吡唑-4-甲酰胺;
-羧酸吗啉化物:烯酰吗啉(dimethomorph)、氟吗啉(flumorph);
-苯甲酰胺类:氟联苯菌(flumetover)、氟吡菌胺(fluopicolide)、氟吡菌酰胺(fluopyram)、苯酰菌胺(zoxamide)、N-(3-乙基-3,5,5-三甲基环己基)-3-甲酰氨基-2-羟基苯甲酰胺;
-其他羧酰胺:氯环丙酰胺(carpropamid)、双氯氰菌胺(diclocymet)、双炔酰菌胺(mandipropamid)、土霉素(oxytetracyclin)、硅噻菌胺(silthiofam)、N-(6-甲氧基吡啶-3-基)环丙烷甲酰胺;
唑类
-三唑类:氧环唑(azaconazole)、双苯三唑醇(bitertanol)、糠菌唑(bromuconazole)、环唑醇(cyproconazole)、噁醚唑(difenoconazole)、烯唑醇(diniconazole)、高效烯唑醇(diniconazole-M)、氧唑菌(epoxiconazole)、腈苯唑(fenbuconazole)、喹唑菌酮(fluquinconazole)、氟硅唑(flusilazole)、粉唑醇(flutriafol)、己唑醇(hexaconazole)、酰胺唑(imibenconazole)、环戊唑醇(ipconazole)、环戊唑菌(metconazole)、腈菌唑(myclobutanil)、恶咪唑(oxpoconazole)、多效唑(paclobutrazole)、戊菌唑(penconazole)、丙环唑(propiconazole)、丙硫菌唑(prothioconazole)、硅氟唑(simeconazole)、戊唑醇(tebuconazole)、氟醚唑(tetraconazole)、唑菌醇(triadimenol)、三唑酮(triadimefon)、戊叉唑菌(triticonazole)、烯效唑(uniconazole)、1-(4-氯苯基)-2-([1,2,4]三唑-1-基)环庚醇;
-咪唑类:氰霜唑(cyazofamid)、抑霉唑(imazalil)、硫酸抑霉唑(imazalil-sulfate)、稻瘟酯(pefurazoate)、丙氯灵(prochloraz)、氟菌唑(triflumizole);
-苯并咪唑类:苯菌灵(benomyl)、多菌灵(carbendazim)、麦穗宁(fuberidazole)、涕必灵(thiabendazole);
-其他:噻唑菌胺(ethaboxam)、氯唑灵(etridiazole)、土菌消(hymexazole)、1-(4-氯苯基)-1-(丙炔-2-基氧基)-3-(4-(3,4-二甲氧基苯基)异噁唑-5-基)丙-2-酮;
含氮杂环基化合物
-吡啶类:氟啶胺(fluazinam)、啶斑肟(pyrifenox)、3-[5-(4-氯苯基)-2,3-二甲基异噁唑烷-3-基]吡啶、2,3,5,6-四氯-4-甲磺酰基吡啶、3,4,5-三氯吡啶-2,6-二甲腈、N-(1-(5-溴-3-氯吡啶-2-基)乙基)-2,4-二氯烟酰胺、N-((5-溴-3-氯吡啶-2-基)甲基)-2,4-二氯烟酰胺;
-嘧啶类:磺嘧菌灵(bupirimate)、环丙嘧啶(cyprodinil)、diflumetorim、嘧菌腙(ferimzone)、异嘧菌醇(fenarimol)、嘧菌胺(mepanipyrim)、氯草定(nitrapyrin)、氟苯嘧啶醇(nuarimol)、二甲嘧菌胺(pyrimethanil);
-吡咯类:氟噁菌(fludioxonil)、拌种咯(fenpiclonil);
-吗啉类:4-十二烷基-2,6-二甲基吗啉(aldimorph)、吗菌灵(dodemorph)、吗菌灵乙酸酯(dodemorph-acetate)、丁苯吗啉(fenpropimorph)、克啉菌(tridemorph);
-二羧酰亚胺类:唑呋草(fluoroimide)、异丙定(iprodione)、杀菌利(procymidone)、烯菌酮(vinclozolin);
-其他:噻二唑素(acibenzolar-S-methyl)、吲唑磺菌胺(amisulbrom)、敌菌灵(anilazine)、灭瘟素(blasticidin-S)、敌菌丹(captafol)、克菌丹(captan)、灭螨猛(quinomethionate)、棉隆(dazomet)、咪菌威(debacarb)、哒菌清(diclomezine)、野燕枯(difenzoquat)、野燕枯硫酸二甲酯(difenzoquat-methyl sulfate)、噁唑酮菌(famoxadone)、咪唑菌酮(fenamidone)、氰菌胺(fenoxanil)、苯锈啶(fenpropidin)、灭菌丹(folpet)、异噻菌酮(octhilinone)、噁喹酸(oxolinic acid)、粉病灵(piperalin)、噻菌灵(probenazole)、丙氧喹啉(proquinazid)、咯喹酮(pyroquilon)、喹氧灵(quinoxyfen)、咪唑嗪(triazoxide)、三环唑(tricyclazole)、嗪氨灵(triforine)、5-氯-7-(4-甲基哌啶-1-基)-6-(2,4,6-三氟苯基)-[1,2,4]三唑并[1,5-a]嘧啶、2-丁氧基-6-碘-3-丙基苯并吡喃-4-酮;
氨基甲酸盐和二硫代氨基甲酸盐
-硫代-和二硫代氨基甲酸盐类:福美铁(ferbam)、代森锰锌(mancozeb)、代森锰(maneb)、威百亩(metam)、磺菌威(methasulfocarb)、代森联(metiram)、甲基代森锌(propineb)、福美双(thiram)、代森锌(zineb)、福美锌(ziram);
-氨基甲酸盐类:乙霉威(diethofencarb)、苯噻菌胺(benthiavalicarb)、异丙菌胺(iprovalicarb)、百维灵(propamocarb)、百维灵盐酸盐(propamocarb hydrochloride)、valiphenal、N-(1-(1-(4-氰基苯基)乙磺酰基)丁-2-基)氨基甲酸(4-氟苯基)酯;
其他杀真菌剂
-胍类:多果定(dodine)、多果定游离碱(dodine-free base)、双胍辛胺(guazatine)、乙酸双胍辛胺(guazatine-acetate)、双胍辛(iminoctadine)、双胍辛醋酸盐(iminoctadine-triacetate)、双胍三辛烷基苯磺酸盐(iminoctadine-tris(albesilate));
-抗生素类:春雷素(kasugamycin)、水合春雷素盐酸盐(kasugamycin-hydrochloride-hydrate)、多氧霉素(polyoxins)、链霉素(streptomycin)、井冈霉素(validamycin A);
-硝基苯基衍生物:乐杀螨(binapacryl)、氯硝胺(dicloran)、敌螨通(dinobuton)、敌螨普(dinocap)、异丙消(nitrothal-isopropyl)、四氯硝基苯(tecnazen);
-有机金属化合物类:三苯基锡盐,例如薯瘟锡(fentin-acetate)、三苯基氯化锡(fentin-chloride)、毒菌锡(fentin-hydroxide);
-含硫的杂环基化合物:稻瘟灵(isoprothiolane)、二噻农(dithianon);
-有机磷化合物:克瘟散(edifenphos)、藻菌磷(fosetyl)、乙膦铝(fosetyl-aluminum)、异稻瘟净(iprobenfos)、定菌磷(pyrazophos)、甲基立枯磷(tolclofos-methyl);
-有机氯化合物:百菌清(chlorothalonil)、抑菌灵(dichlofluanid)、双氯酚(dichlorophen)、磺菌胺(flusulfamide)、六氯苯(hexachlorobenzene)、戊菌隆(pencycuron)、五氯酚(pentachlorophenol)及其盐、四氯苯酞(phthalide)、五氯硝基苯(quintozene)、甲基托布津(thiophanate-methyl)、对甲抑菌灵(tolylfluanid)、N-(4-氯-2-硝基苯基)-N-乙基-4-甲基苯磺酰胺;
-无机活性化合物:亚磷酸及其盐、硫、波尔多液(Bordeaux混合物),铜盐如醋酸铜、氢氧化铜、王铜、碱式硫酸铜;
-其他:联苯、溴硝醇(bronopol)、环氟菌胺(cyflufenamid)、清菌脲(cymoxanil)、二苯胺、苯菌酮(metrafenone)、灭粉霉素(mildiomycin)、喹啉铜(oxine-copper)、调环酸钙(prohexadione-calcium)、螺噁茂胺(spiroxamine)、对甲抑菌灵、N-(环丙基甲氧亚氨基-(6-二氟甲氧基-2,3-二氟苯基)甲基)-2-苯基乙酰胺、N′-(4-(4-氯-3-三氟甲基苯氧基)-2,5-二甲基苯基)-N-乙基-N-甲基甲脒、N′-(4-(4-氟-3-三氟甲基苯氧基)-2,5-二甲基苯基)-N-乙基-N-甲基甲脒、N′-(2-甲基-5-三氟甲基-4-(3-三甲基硅烷基丙氧基)苯基)-N-乙基-N-甲基甲脒、N′-(5-二氟甲基-2-甲基-4-(3-三甲基硅烷基丙氧基)苯基)-N-乙基-N-甲基甲脒。
因此,本发明进一步涉及表B中所列组合物,表B的每行对应于包含式I化合物(组分1)-优选为在本文中作为优选描述的化合物之一且包含在每种情况下在所述行中所示的其他活性化合物(组分2)的杀真菌组合物。根据本发明的一个实施方案,在表B的每行中的组分1在每种情况下为在表1-54中所具体列举的式I化合物之一。
表B
行 | 组分1 | 组分2 |
B-1 | 式I化合物 | 腈嘧菌酯 |
B-2 | 式I化合物 | 醚菌胺 |
B-3 | 式I化合物 | 烯肟菌酯 |
B-4 | 式I化合物 | 氟嘧菌酯 |
B-5 | 式I化合物 | 亚胺菌 |
B-6 | 式I化合物 | 叉氨苯酰胺 |
B-7 | 式I化合物 | 肟醚菌胺 |
B-8 | 式I化合物 | 啶氧菌酯 |
行 | 组分1 | 组分2 |
B-9 | 式I化合物 | 唑菌胺酯 |
B-10 | 式I化合物 | pyribencarb |
B-11 | 式I化合物 | 肟菌酯 |
B-12 | 式I化合物 | 2-(2-(6-(3-氯-2-甲基苯氧基)-5-氟嘧啶-4-基氧基)苯基)-2-甲氧亚氨基-N-甲基乙酰胺 |
B-13 | 式I化合物 | 2-(邻-((2,5-二甲基苯氧基亚甲基)苯基)-3-甲氧基丙烯酸甲酯 |
B-14 | 式I化合物 | 3-甲氧基-2-(2-(N-(4-甲氧基苯基)环丙烷甲亚胺酰基硫基甲基)苯基)丙烯酸甲酯 |
B-15 | 式I化合物 | 苯霜灵 |
B-16 | 式I化合物 | 精苯霜灵 |
B-17 | 式I化合物 | 麦锈灵 |
B-18 | 式I化合物 | bixafen |
B-19 | 式I化合物 | 啶酰菌胺 |
B-20 | 式I化合物 | 萎锈灵 |
B-21 | 式I化合物 | 呋菌胺 |
B-22 | 式I化合物 | 环酰菌胺 |
B-23 | 式I化合物 | 氟酰胺 |
B-24 | 式I化合物 | 呋吡唑灵 |
B-25 | 式I化合物 | 异噻菌胺 |
B-26 | 式I化合物 | kiralaxyl |
B-27 | 式I化合物 | 丙氧灭绣胺 |
B-28 | 式I化合物 | 甲霜灵 |
B-29 | 式I化合物 | 甲呋酰胺 |
B-30 | 式I化合物 | 噁霜灵 |
B-31 | 式I化合物 | 氧化萎锈灵 |
B-32 | 式I化合物 | 吡噻菌胺 |
B-33 | 式I化合物 | 溴氟唑菌 |
B-34 | 式I化合物 | 叶枯酞 |
B-35 | 式I化合物 | 噻酰菌胺 |
B-36 | 式I化合物 | 2-氨基-4-甲基噻唑-5-甲酰苯胺 |
B-37 | 式I化合物 | 2-氯-N-(1,1,3-三甲基茚满-4-基)烟酰胺 |
B-38 | 式I化合物 | N-(3′,4′-二氯-5-氟联苯-2-基)-3-二氟甲基-1-甲基-1H-吡唑-4-甲酰胺 |
B-39 | 式I化合物 | 5-氟-1,3-二甲基-1H-吡唑-4-甲酸[2-(1,3-二甲基丁基)苯基]酰胺 |
B-40 | 式I化合物 | N-(4′-氯-3′,5-二氟联苯-2-基)-3-二氟甲基-1-甲基 |
行 | 组分1 | 组分2 |
-1H-吡唑-4-甲酰胺 | ||
B-41 | 式I化合物 | N-(4′-氯-3′,5-二氟联苯-2-基)-3-三氟甲基-1-甲基-1H-吡唑-4-甲酰胺 |
B-42 | 式I化合物 | N-(3′,4′-二氯-5-氟联苯-2-基)-3-三氟甲基-1-甲基-1H-吡唑-4-甲酰胺 |
B-43 | 式I化合物 | N-(3′,5-二氟-4′-甲基联苯-2-基)-3-二氟甲基-1-甲基-1H-吡唑-4-甲酰胺 |
B-44 | 式I化合物 | N-(3′,5-二氟-4′-甲基联苯-2-基)-3-三氟甲基-1-甲基-1H-吡唑-4-甲酰胺 |
B-45 | 式I化合物 | N-(2-双环丙-2-基苯基)-3-二氟甲基-1-甲基-1H-吡唑-4-甲酰胺 |
B-46 | 式I化合物 | N-(顺式-2-双环丙-2-基苯基)-3-二氟甲基-1-甲基-1H-吡唑-4-甲酰胺 |
B-47 | 式I化合物 | N-(反式-2-双环丙-2-基苯基)-3-二氟甲基-1-甲基-1H-吡唑-4-甲酰胺 |
B-48 | 式I化合物 | 烯酰吗啉 |
B-49 | 式I化合物 | 氟吗啉 |
B-50 | 式I化合物 | 氟联苯菌 |
B-51 | 式I化合物 | 氟吡菌胺(picobenzamid) |
B-52 | 式I化合物 | 氟吡菌酰胺 |
B-53 | 式I化合物 | 苯酰菌胺 |
B-54 | 式I化合物 | N-(3-乙基-3,5,5-三甲基环己基)-3-甲酰氨基-2-羟基苯甲酰胺 |
B-55 | 式I化合物 | 氯环丙酰胺 |
B-56 | 式I化合物 | 双氯氰菌胺 |
B-57 | 式I化合物 | 双炔酰菌胺 |
B-58 | 式I化合物 | 土霉素 |
B-59 | 式I化合物 | 硅噻菌胺 |
B-60 | 式I化合物 | N-(6-甲氧基吡啶-3-基)环丙烷甲酰胺 |
B-61 | 式I化合物 | 氧环唑 |
B-62 | 式I化合物 | 双苯三唑醇 |
B-63 | 式I化合物 | 糠菌唑 |
B-64 | 式I化合物 | 环唑醇 |
B-65 | 式I化合物 | 噁醚唑 |
B-66 | 式I化合物 | 烯唑醇 |
B-67 | 式I化合物 | 高效烯唑醇 |
B-68 | 式I化合物 | 烯菌灵 |
行 | 组分1 | 组分2 |
B-69 | 式I化合物 | 氧唑菌 |
B-70 | 式I化合物 | 腈苯唑 |
B-71 | 式I化合物 | 氟硅唑 |
B-72 | 式I化合物 | 喹唑菌酮 |
B-73 | 式I化合物 | 粉唑醇 |
B-74 | 式I化合物 | 己唑醇 |
B-75 | 式I化合物 | 酰胺唑 |
B-76 | 式I化合物 | 环戊唑醇 |
B-77 | 式I化合物 | 环戊唑菌 |
B-78 | 式I化合物 | 腈菌唑 |
B-79 | 式I化合物 | 恶咪唑 |
B-80 | 式I化合物 | 多效唑 |
B-81 | 式I化合物 | 戊菌唑 |
B-82 | 式I化合物 | 丙环唑 |
B-83 | 式I化合物 | 丙硫菌唑 |
B-84 | 式I化合物 | 硅氟唑 |
B-85 | 式I化合物 | 戊唑醇 |
B-86 | 式I化合物 | 氟醚唑 |
B-87 | 式I化合物 | 唑菌醇 |
B-88 | 式I化合物 | 三唑酮 |
B-89 | 式I化合物 | 戊叉唑菌 |
B-90 | 式I化合物 | 烯效唑 |
B-91 | 式I化合物 | 1-(4-氯苯基)-2-([1,2,4]三唑-1-基)环庚醇 |
B-92 | 式I化合物 | 氰霜唑 |
B-93 | 式I化合物 | 抑霉唑 |
B-94 | 式I化合物 | 硫酸抑霉唑 |
B-95 | 式I化合物 | 稻瘟酯 |
B-96 | 式I化合物 | 丙氯灵 |
B-97 | 式I化合物 | 氟菌唑 |
B-98 | 式I化合物 | 苯菌灵 |
B-99 | 式I化合物 | 多菌灵 |
B-100 | 式I化合物 | 麦穗宁 |
B-101 | 式I化合物 | 涕必灵 |
B-102 | 式I化合物 | 噻唑菌胺 |
B-103 | 式I化合物 | 氯唑灵 |
B-104 | 式I化合物 | 土菌消 |
行 | 组分1 | 组分2 |
B-105 | 式I化合物 | 氟啶胺 |
B-106 | 式I化合物 | 啶斑肟 |
B-107 | 式I化合物 | 1-(4-氯苯基)-1-(丙炔-2-基氧基)-3-(4-(3,4-二甲氧基苯基)异噁唑-5-基)丙-2-酮 |
B-108 | 式I化合物 | 3-[5-(4-氯苯基)-2,3-二甲基异噁唑烷-3-基]吡啶 |
B-109 | 式I化合物 | 2,3,5,6-四氯-4-甲磺酰基吡啶 |
B-110 | 式I化合物 | 3,4,5-三氯吡啶-2,6-二甲腈 |
B-111 | 式I化合物 | N-(1-(5-溴-3-氯吡啶-2-基)乙基)-2,4-二氯烟酰胺 |
B-112 | 式I化合物 | N-((5-溴-3-氯吡啶-2-基)甲基)-2,4-二氯烟酰胺 |
B-113 | 式I化合物 | 磺嘧菌灵 |
B-114 | 式I化合物 | 环丙嘧啶 |
B-115 | 式I化合物 | diflumetorim |
B-116 | 式I化合物 | 嘧菌腙 |
B-117 | 式I化合物 | 异嘧菌醇 |
B-118 | 式I化合物 | 嘧菌胺 |
B-119 | 式I化合物 | 氯草定 |
B-120 | 式I化合物 | 氟苯嘧啶醇 |
B-121 | 式I化合物 | 二甲嘧菌胺 |
B-122 | 式I化合物 | 氟噁菌 |
B-123 | 式I化合物 | 拌种咯 |
B-124 | 式I化合物 | 4-十二烷基-2,6-二甲基吗啉 |
B-125 | 式I化合物 | 吗菌灵 |
B-126 | 式I化合物 | 吗菌灵乙酸酯 |
B-127 | 式I化合物 | 丁苯吗啉 |
B-128 | 式I化合物 | 克啉菌 |
B-129 | 式I化合物 | 唑呋草 |
B-130 | 式I化合物 | 异丙定 |
B-131 | 式I化合物 | 杀菌利 |
B-132 | 式I化合物 | 烯菌酮 |
B-133 | 式I化合物 | 噻二唑素 |
B-134 | 式I化合物 | 吲唑磺菌胺 |
B-135 | 式I化合物 | 敌菌灵 |
B-136 | 式I化合物 | 灭瘟素 |
B-137 | 式I化合物 | 克菌丹 |
B-138 | 式I化合物 | 敌菌丹 |
B-139 | 式I化合物 | 灭螨猛(chinomethionat) |
行 | 组分1 | 组分2 |
B-140 | 式I化合物 | 棉隆 |
B-141 | 式I化合物 | 咪菌威 |
B-142 | 式I化合物 | 哒菌清 |
B-143 | 式I化合物 | 野燕枯 |
B-144 | 式I化合物 | 野燕枯硫酸二甲酯 |
B-145 | 式I化合物 | 噁唑酮菌 |
B-146 | 式I化合物 | 咪唑菌酮 |
B-147 | 式I化合物 | 氰菌胺 |
B-148 | 式I化合物 | 苯锈啶 |
B-149 | 式I化合物 | 灭菌丹 |
B-150 | 式I化合物 | 异噻菌酮 |
B-151 | 式I化合物 | 噁喹酸 |
B-152 | 式I化合物 | 粉病灵 |
B-153 | 式I化合物 | 噻菌灵 |
B-154 | 式I化合物 | 丙氧喹啉 |
B-155 | 式I化合物 | 咯喹酮 |
B-156 | 式I化合物 | 喹氧灵 |
B-157 | 式I化合物 | 咪唑嗪 |
B-158 | 式I化合物 | 三环唑 |
B-159 | 式I化合物 | 嗪氨灵 |
B-160 | 式I化合物 | 5-氯-7-(4-甲基哌啶-1-基)-6-(2,4,6-三氟苯基)-[1,2,4]三唑并[1,5-a]嘧啶 |
B-161 | 式I化合物 | 2-丁氧基-6-碘-3-丙基苯并吡喃-4-酮 |
B-162 | 式I化合物 | 福美铁 |
B-163 | 式I化合物 | 代森锰锌 |
B-164 | 式I化合物 | 代森锰 |
B-165 | 式I化合物 | 代森联 |
B-166 | 式I化合物 | 威百亩 |
B-167 | 式I化合物 | 磺菌威 |
B-168 | 式I化合物 | 甲基代森锌 |
B-169 | 式I化合物 | 福美双 |
B-170 | 式I化合物 | 代森锌 |
B-171 | 式I化合物 | 福美锌 |
B-172 | 式I化合物 | 乙霉成 |
B-173 | 式I化合物 | flubenthiavalicarb |
B-174 | 式I化合物 | 异丙菌胺 |
行 | 组分1 | 组分2 |
B-175 | 式I化合物 | 百维灵 |
B-176 | 式I化合物 | 百维灵盐酸盐 |
B-177 | 式I化合物 | 3-(4-氯苯基)-3-(2-异丙氧羰基氨基-3-甲基丁酰氨基)丙酸甲酯 |
B-178 | 式I化合物 | valiphenal |
B-179 | 式I化合物 | N-(1-(1-(4-氰基苯基)乙磺酰基)丁-2-基)氨基甲酸4-氟苯基酯 |
B-180 | 式I化合物 | 多果定 |
B-181 | 式I化合物 | 多果定游离碱 |
B-182 | 式I化合物 | 双胍辛 |
B-183 | 式I化合物 | 双胍辛醋酸盐 |
B-184 | 式I化合物 | 双胍三辛烷基苯磺酸盐 |
B-185 | 式I化合物 | 双胍辛胺 |
B-186 | 式I化合物 | 乙酸双胍辛胺 |
B-187 | 式I化合物 | 春雷素 |
B-188 | 式I化合物 | 水合春雷素盐酸盐 |
B-189 | 式I化合物 | 多氧霉素 |
B-190 | 式I化合物 | 链霉素 |
B-191 | 式I化合物 | 井冈霉素 |
B-192 | 式I化合物 | 乐杀螨 |
B-193 | 式I化合物 | 氯硝胺 |
B-194 | 式I化合物 | 敌螨通 |
B-195 | 式I化合物 | 敌螨普 |
B-196 | 式I化合物 | 异丙消 |
B-197 | 式I化合物 | 四氯硝基苯 |
B-198 | 式I化合物 | 薯瘟锡 |
B-199 | 式I化合物 | 三苯基氯化锡 |
B-200 | 式I化合物 | 毒菌锡 |
B-201 | 式I化合物 | 稻瘟灵 |
B-202 | 式I化合物 | 二噻农 |
B-203 | 式I化合物 | 克瘟散 |
B-204 | 式I化合物 | 藻菌磷 |
B-205 | 式I化合物 | 乙膦铝 |
B-206 | 式I化合物 | 异稻瘟净 |
B-207 | 式I化合物 | 定菌磷 |
B-208 | 式I化合物 | 甲基立枯磷 |
行 | 组分1 | 组分2 |
B-209 | 式I化合物 | 百菌清 |
B-210 | 式I化合物 | 抑菌灵 |
B-211 | 式I化合物 | 双氯酚 |
B-212 | 式I化合物 | 磺菌胺 |
B-213 | 式I化合物 | 六氯苯 |
B-214 | 式I化合物 | 戊菌隆 |
B-215 | 式I化合物 | 五氯酚及其盐 |
B-216 | 式I化合物 | 四氯苯酞 |
B-217 | 式I化合物 | 五氯硝基苯 |
B-218 | 式I化合物 | 甲基托布津 |
B-219 | 式I化合物 | 对甲抑菌灵 |
B-220 | 式I化合物 | N-(4-氯-2-硝基苯基)-N-乙基-4-甲基苯磺酰胺 |
B-221 | 式I化合物 | 亚磷酸及其盐 |
B-222 | 式I化合物 | 硫 |
B-223 | 式I化合物 | 波尔多液 |
B-224 | 式I化合物 | 醋酸铜 |
B-225 | 式I化合物 | 氢氧化铜 |
B-226 | 式I化合物 | 王铜 |
B-227 | 式I化合物 | 碱式硫酸铜 |
B-228 | 式I化合物 | 联苯 |
B-229 | 式I化合物 | 溴硝醇 |
B-230 | 式I化合物 | 环氟菌胺 |
B-231 | 式I化合物 | 清菌脲 |
B-232 | 式I化合物 | 二苯胺 |
B-233 | 式I化合物 | 苯菌酮 |
B-234 | 式I化合物 | 灭粉霉素 |
B-235 | 式I化合物 | 喹啉铜 |
B-236 | 式I化合物 | 调环酸钙 |
B-237 | 式I化合物 | 螺噁茂胺 |
B-238 | 式I化合物 | 对甲抑菌灵 |
B-239 | 式I化合物 | N-(环丙基甲氧亚氨基-(6-二氟甲氧基-2,3-二氟苯基)甲基)-2-苯基乙酰胺 |
B-240 | 式I化合物 | N′-(4-(4-氯-3-三氟甲基苯氧基)-2,5-二甲基苯基)-N-乙基-N-甲基甲脒 |
B-241 | 式I化合物 | N′-(4-(4-氟-3-三氟甲基苯氧基)-2,5-二甲基苯基)-N-乙基-N-甲基甲脒 |
行 | 组分1 | 组分2 |
B-242 | 式I化合物 | N′-(2-甲基-5-三氟甲基-4-(3-三甲基硅烷基丙氧基)苯基)-N-乙基-N-甲基甲脒 |
B-243 | 式I化合物 | N′-(5-二氟甲基-2-甲基-4-(3-三甲基硅烷基丙氧基)苯基)-N-乙基-N-甲基甲脒 |
上面作为组分2提到的活性化合物II、其制备及其对真菌病原体的效果广泛已知(参见:http://www.hclrss.demon.co.uk/index.html);它们可以市购。具有IUPAC命名的化合物、其制备及其杀真菌活性同样是已知的[参见EP-A 226 917;EP-A 10 28 125;EP-A 10 35 122;EP-A 12 01 648;WO 98/46608;WO 99/24413;WO 03/14103;WO 03/053145;WO 03/066609;WO 04/049804]。
合成实施例
a)合成1-氯-2-(3-氟苯基)-3-(2-氯苯基)丙-2-醇
将镁屑(1.09g,44.8mmol)加入邻氯苄基氯(0.1ml,0.8mmol)在无水乙醚(20ml)和碘中的溶液中。一旦放热反应开始,在回流下将另外的苄基氯(7.10g,44.0mmol)滴加到反应溶液中。将混合物在回流下再搅拌2小时,然后冷却到0℃,并滴加2-氯-1-(2-氯苯基)乙酮(3.87g,22.4mmol)在无水甲苯(10ml)中的溶液。然后将混合物在室温下搅拌3小时并再次冷却到0℃,加入氯化铵水溶液(10ml)。将水相反复用乙酸乙酯萃取,将合并的有机相干燥(硫酸钠)并蒸除溶剂。残余物(约8.6g)不经提纯用于下一反应步骤。
b)合成(Z)-1-[3-氯-1-(2-氯苯基)丙-1-烯-2-基]-3-氟苯
在0℃下将乙酸酐(2.6ml,26.9mmol)以及随后浓硫酸(0.1ml,1.9mmol)加入来自步骤a)的在1,4-二噁烷/THF(49ml,10∶1)中的叔醇(8.6g,~22.4mmol)。将混合物温热到室温并搅拌18小时。然后再次将混合物冷却到0℃,加入盐水(20ml)并将混合物用含水NaOH中和。在用乙酸乙酯萃取之后,合并有机相,在硫酸钠上干燥并除去溶剂。通过柱层析(硅胶)得到浅黄色油状所需产物(1.70g,在两步上为27%)。1H NMR(300MHz,CDCl3)δ7.65-7.62(1H),7.46-7.27(6H),7.09-7.03(1H),7.1(1H),4.48(2H)。
c)合成反-2-(3-氟苯基)-2-(氯甲基)-3-(2-氯苯基)环氧乙烷
将前一步骤的反应产物(1.60g,6.0mmol)溶于乙酸(60ml)中并加入马来酸酐(11.8g,120.6mmol)和H2O2(50%水溶液,3.4ml,60.3mmol)。将反应混合物在45℃下搅拌3天,然后冷却到室温,加入硫代硫酸钠水溶液(10%)。在用水(20ml)稀释后,将混合物用二氯甲烷萃取并将合并的有机相用饱和盐水洗涤。在硫酸钠上干燥之后,过滤该混合物并减压除去溶剂。残余物通过柱层析(硅胶,己烷/乙酸乙酯)提纯。得到无色固体形式的环氧化物(732mg,41%)。
1H NMR(300MHz,CDCl3)δ7.50-7.47(1H),7.44-7.28(6H),7.11-7.04(1H),4.24(1H),3.88(1H),3.34(1H)。
d)合成1-[(反)-2-(3-氟苯基)-3-(2-氯苯基)环氧乙烷-2-基]甲基]-1H-1,2,4-三唑
在室温下将1,2,4-三唑(347mg,4.9mmol)和氢化钠(216mg,5.4mmol)加入来自c)的环氧化物(732mg,2.4mmol)在无水DMF(10ml)中的溶液中。将该混合物在60℃下加热20小时,然后再在75℃下搅拌4小时。然后将反应溶液冷却至室温,加入乙酸乙酯并将混合物用饱和盐水洗涤。分离出有机相并在硫酸钠上干燥,减压除去溶剂。以此方式得到的残余物通过柱层析(硅胶,己烷/乙酸乙酯)提纯。合并各级分,得到熔点为164-166℃的无色固体形式的标题化合物(720mg,89%)。
1H NMR(300MHz,CDCl3)δ7.88(1H),7.79(1H),7.60-7.57(1H),7.49-7.29(4H),7.23-7.11(2H),7.05-6.99(1H),4.79(1H),4.24(1H),3.96(1H)。
以类似方式合成表2所列式I化合物。
表2:
化合物 | 取代基A | 物理数据 |
2.1 | 4-氯苯基 | 98-100 |
2.2 | 3-氯苯基 | 7.93(1H),7.83(1H),7.49(1H),7.39-7.29(4H),7.17-6.98(3H),4.77(1H),4.16(1H),4.12(1H) |
2.3 | 4-氟苯基 | 73-75 |
2.4 | 2-氯苯基 | 164-166 |
Claims (8)
2.根据权利要求1的化合物,其中苯基被1-3个下列取代基取代:卤素、NO2、氨基、C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷基、C1-C4卤代烷氧基、C1-C4烷基氨基、C1-C4二烷基氨基、硫代或C1-C4烷硫基。
3.根据权利要求2的化合物,其中苯基被1-3个下列取代基取代:卤素、C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷基或C1-C4卤代烷氧基。
4.根据权利要求3的化合物,其中苯基被1-3个下列取代基取代:卤素、C1-C4烷基或C1-C4烷氧基。
5.根据权利要求1-4中任一项的式I化合物或其酸加成盐或金属盐在防治植物病原性真菌中的用途。
6.一种作物保护组合物,包含固体或液体载体和根据权利要求1-4中任一项的式I化合物或其酸加成盐或金属盐。
7.种子,包含至少一种根据权利要求1-4中任一项的式I化合物或其酸加成盐或金属盐。
8.一种防治植物病原性真菌的方法,其中用有效量的根据权利要求1-4中任一项的式I化合物或其酸加成盐或金属盐处理真菌或要防止真菌侵袭的材料、植物、土壤或种子。
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CN103988838A (zh) * | 2013-04-07 | 2014-08-20 | 海南正业中农高科股份有限公司 | 含有环氟菌胺与乙嘧酚或氟嘧菌胺的杀菌组合物 |
CN104012543A (zh) * | 2013-04-07 | 2014-09-03 | 海南正业中农高科股份有限公司 | 含有环氟菌胺与氟环唑的杀菌组合物 |
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-
2007
- 2007-12-04 BR BRPI0720572-4A patent/BRPI0720572A2/pt not_active IP Right Cessation
- 2007-12-04 US US12/519,973 patent/US7994340B2/en not_active Expired - Fee Related
- 2007-12-04 WO PCT/EP2007/063213 patent/WO2008077724A1/de active Application Filing
- 2007-12-04 JP JP2009541953A patent/JP2010513367A/ja active Pending
- 2007-12-04 EP EP07847722A patent/EP2096921A1/de not_active Withdrawn
- 2007-12-04 CN CNA2007800478505A patent/CN101568259A/zh active Pending
- 2007-12-20 CL CL200703731A patent/CL2007003731A1/es unknown
- 2007-12-21 AR ARP070105873A patent/AR064508A1/es not_active Application Discontinuation
- 2007-12-21 TW TW096149560A patent/TW200833246A/zh unknown
- 2007-12-21 UY UY30831A patent/UY30831A1/es unknown
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2008
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103988838A (zh) * | 2013-04-07 | 2014-08-20 | 海南正业中农高科股份有限公司 | 含有环氟菌胺与乙嘧酚或氟嘧菌胺的杀菌组合物 |
CN104012543A (zh) * | 2013-04-07 | 2014-09-03 | 海南正业中农高科股份有限公司 | 含有环氟菌胺与氟环唑的杀菌组合物 |
CN103988838B (zh) * | 2013-04-07 | 2016-09-07 | 海南正业中农高科股份有限公司 | 含有环氟菌胺与乙嘧酚或氟嘧菌胺的杀菌组合物 |
Also Published As
Publication number | Publication date |
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US7994340B2 (en) | 2011-08-09 |
CL2007003731A1 (es) | 2008-04-11 |
JP2010513367A (ja) | 2010-04-30 |
WO2008077724A1 (de) | 2008-07-03 |
TW200833246A (en) | 2008-08-16 |
EP2096921A1 (de) | 2009-09-09 |
BRPI0720572A2 (pt) | 2014-02-04 |
UY30831A1 (es) | 2008-07-03 |
AR064508A1 (es) | 2009-04-08 |
US20100087321A1 (en) | 2010-04-08 |
PE20081533A1 (es) | 2008-12-12 |
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