CN101484009A - 芳基甲酸联苯基酰胺在种子处理中的用途 - Google Patents
芳基甲酸联苯基酰胺在种子处理中的用途 Download PDFInfo
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- CN101484009A CN101484009A CNA2007800252759A CN200780025275A CN101484009A CN 101484009 A CN101484009 A CN 101484009A CN A2007800252759 A CNA2007800252759 A CN A2007800252759A CN 200780025275 A CN200780025275 A CN 200780025275A CN 101484009 A CN101484009 A CN 101484009A
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- seed
- bacterium
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- fluorine
- plant
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- 239000001257 hydrogen Substances 0.000 claims abstract description 15
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Classifications
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- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
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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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
- A01N37/24—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides containing at least one oxygen or sulfur atom being directly attached to the same aromatic ring system
-
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
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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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
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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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
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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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
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- General Health & Medical Sciences (AREA)
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Abstract
本发明涉及式(I)的芳基甲酸联苯基酰胺在处理种子以保护由其生长的植物在萌发后免受叶面植物病原性真菌侵袭中的用途和相应的处理种子以保护植物在萌发后免受叶面植物病原性真菌侵袭的方法,其中X为卤素或甲基;n为0、1或2;Y为氰基、硝基、卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4卤代烷硫基、C1-C4烷氧亚氨基甲基或烯丙氧基亚氨基甲基;m为0-5;Ar为式IIa、IIb或IIc的芳基,其中R1为氢、卤素、C1-C4烷基或C1-C4卤代烷基,R2为C1-C4烷基,R3为氢、卤素或甲基,R4为氢、卤素或C1-C4烷基,R5为C1-C4烷基或C1-C4卤代烷基,Z为CH或N,和R6为卤素、C1-C4烷基或C1-C4卤代烷基。本发明还涉及包含式(I)的芳基甲酸联苯基酰胺的种子处理配制剂和用其处理的种子。
Description
本发明涉及一种保护植物在萌发后免受叶面植物病原性真菌侵袭的方法,其包括用有效量的至少一种式I的芳基甲酸联苯基酰胺或其可农用盐处理由其生长植物的种子:
其中
X为卤素或甲基;
n为0、1或2,其中在n为2的情况下,基团X可具有相同或不同含义;
Y为氰基、硝基、卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4卤代烷硫基、C1-C4烷氧亚氨基甲基或烯丙氧基亚氨基甲基;
m为0-5,其中在m为2、3、4或5的情况下,基团Y可具有相同或不同含义;
Ar为式IIa、IIb或IIc的芳基:
其中
R1为氢、卤素、C1-C4烷基或C1-C4卤代烷基,
R2为C1-C4烷基,
R3为氢、卤素或甲基,
R4为氢、卤素或C1-C4烷基,
R5为C1-C4烷基或C1-C4卤代烷基,
Z为CH或N,和
R6为卤素、C1-C4烷基或C1-C4卤代烷基。
本发明进一步涉及至少一种如上所定义的式I的芳基甲酸联苯基酰胺或其可农用盐在处理种子以保护由该种子生长的植物在萌发后免受叶面植物病原性真菌侵袭中的用途。
本发明还涉及种子处理组合物和种子。
直到近年来,在豆类植物(尤其是大豆)栽培的最重要区域,还没有受到有害真菌的具有经济重要性的侵染。
然而,近年来,在南美大豆作物受到有害真菌豆薯层锈菌(Phakopsorapachyrhizi)或山马蝗层锈菌(Phakopsora meibomiae)的严重锈病侵染已经增加。存在明显的收获和产量损失。
最常规的杀真菌剂不适合防治大豆中的锈病,或者它们对锈病真菌的作用不令人满意。
当然,真菌侵袭在其它作物如禾谷类和蔬菜中也是严重的问题。
在萌发之前或过程中的时间中,发芽植物尤其易受到植物病原性真菌的侵袭,不仅是因为发育植物器官的尺寸小使得它们不能应对许多损害,而且因为某些天然的植物防护机制在发育阶段还没有建立。因此,在萌发之前和之后保护植物在减少损害中是有作用的。
然而,向植物或它们的环境常规施加杀真菌剂可能遭受许多不利之处:尤其是如果使用十分广泛,则经常非常快速的产生对杀真菌剂的抗药性,因此必须持续开发新的试剂。杀真菌剂对公众健康和环境的可能的有害影响是公众所关注的。更特别是杀真菌剂的滥用不仅昂贵,而且对农业劳动者具有严重的健康危害;这特别涉及粉剂或可撒粉粉末。因此,明智的是使用尽可能低的剂量。此外,杀真菌剂对土壤性真菌的效力,尤其是对地下物种,叶是非常希望的。真菌的恰当管理要求良好的时间和许多持续的工作并且取决于所用配制剂可能对难以控制的非生物因素如风、温度和降雨非常敏感。通常不希望有杀真菌剂从所需作用位置扩散出(“杀真菌剂漂移”)的可能性。
因此,理想的是,杀真菌剂应以较低的剂量有效、不易于大规模扩散入环境并离开待保护的植物(因此导致不希望的“旁观效应(bystandereffect)”,并适合例如最小的暴露于人类和处理时间的程序。此外,应对宽范围的植物病原性真菌有效,优选结合了快速效果(“击倒”)和长期防治。
本发明的目的是提供一种保护作物免受植物病原性真菌损害的方法。其优选应解决降低剂量率、将击倒活性与长期防治结合和/或适合抗药性管理的问题。令人惊讶地发现用芳基甲酸联苯基酰胺I处理未播种的植物种子不仅保护种子本身,而且还令人惊讶地提供对损害种子或由种子生长的植物的植物病原性真菌的出苗后防治,即种子处理对由处理的种子生长的植物在萌发后以及在植物出苗后具有预防性抗真菌效果。
因此,本发明涉及如上所定义的芳基甲酸联苯基酰胺I在处理种子以保护由其生长的植物在萌发后,和甚至在出苗后免受叶面植物病原性真菌侵袭的方法和一种保护植物在萌发后,和甚至在出苗后免受叶面植物病原性真菌侵袭的方法,其包括用有效量的所述芳基甲酸联苯基酰胺I处理种子。
优选本发明方法和用途用于在出苗后保护植物,尤其是在植物处于生长阶段BBCH 09或更高生长阶段中保护植物(根据BBCH扩充版(extendedscale);German Federal Biological Research Centre for Agriculture andForestry(德国联邦农业和林业生物研究中心);参见www.bba.de/veroeff/bbch/bbcheng.pdf)。该目的通过如上所述和下文所述处理由其生长植物的种子而实现。迄今为止,这是令人惊讶的,式I的芳基甲酸联苯基酰胺仅已知保护种子本身免受真菌侵袭;对由种子生长的植物的预防性杀真菌效果还不是已知的。
本发明提供了数个优点:其集中于对作物和真菌的杀真菌剂效果,因此使对人类暴露和环境副作用以及所需的总剂量最小化且有效对抗地下植物病害以及叶面病原体(即叶面植物病原性真菌)、对非生物因素依赖较小且便于施用。
芳基甲酸联苯基酰胺I例如由EP-A 545099、EP-A 589301、WO99/09013、WO 2005/123689、WO 2005/123690、WO 2003/069995、WO2003/070705、WO 2003/066609和WO 2003/066610已知或者它们可根据其中所述的方法制备。
合适的式I化合物包括所有可能出现的立体异构体(顺/反异构体,对映异构体)及其混合物。立体异构中心例如为烷氧亚氨基甲基或烯丙氧基亚氨基甲基结构部分的碳原子和氮原子以及不对称碳原子。本发明提供了纯对映异构体或非对映异构体或其混合物,纯顺式-和反式-异构体及其混合物的用途。通式I的化合物可以不同互变异构体的形式存在。本发明包括单个互变异构体(若可分离的话)以及互变异构体混合物的用途。
合适的可农用盐尤其为其阴离子对化合物I的杀真菌作用没有不利影响的那些酸的酸加成盐。有用的酸加成盐的阴离子主要为氯离子、溴离子、氟离子、硫酸氢根、硫酸根、磷酸二氢根、磷酸氢根、磷酸根、硝酸根、碳酸氢根、碳酸根、六氟硅酸根、六氟磷酸根、苯甲酸根,以及C1-C4链烷酸的阴离子,优选甲酸根、乙酸根、丙酸根和丁酸根。它们可通过使I与对应阴离子的酸,优选盐酸、氢溴酸、硫酸、磷酸或硝酸反应而形成。
式I化合物可以各种其生物活性可能不同的晶形存在。它们的用途也形成本发明的主题部分。
术语卤素在每种情况下指氟、溴、氯或碘。
本文使用的术语“C1-C4烷基”是指具有1-4个碳原子的支化或未支化饱和烃基,例如甲基、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。
术语“C1-C4烷氧基”是指经由在烷基的任意键处的氧键键接的具有1-4个碳原子的直链或支化烷基(如上所定义)。实例包括甲氧基、乙氧基、丙氧基、异丙氧基、丁氧基、仲丁氧基、异丁氧基和叔丁氧基。
术语“C1-C4烷氧亚氨基甲基”是指经由在烷基的任意键处的O-N=CH-键键接的具有1-4个碳原子的直链或支化烷基(如上所定义)。实例包括甲氧亚氨基甲基、乙氧亚氨基甲基、丙氧亚氨基甲基、异丙氧亚氨基甲基、丁氧亚氨基甲基、仲丁氧亚氨基甲基、异丁氧亚氨基甲基和叔丁氧亚氨基甲基。
术语“C1-C4烷硫基”是指经由在烷基的任意键处的硫键键接的具有1-4个碳原子的直链或支化烷基(如上所定义)。实例包括甲硫基、乙硫基、丙硫基、异丙硫基、丁硫基、仲丁硫基、异丁硫基和叔丁硫基。
用于本文的术语“C1-C4卤代烷基”是指具有1-4个碳原子的直链或支化烷基(如上所定义),其中这些基团中的一些或所有氢原子被如上所定义的卤素替换,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、二氯氟甲基、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、2,2,2-三氯乙基或五氟乙基或C3-C4卤代烷基,如2-氟丙基、3-氟丙基、2,2-二氟丙基、2,3-二氟丙基、2-氯丙基、3-氯丙基、2,3-二氯丙基、2-溴丙基、3-溴丙基、3,3,3-三氟丙基、3,3,3-三氯丙基、2,2,3,3,3-五氟丙基、七氟丙基、1-(氟甲基)-2-氟乙基、1-(氯甲基)-2-氯乙基、1,1,1,3,3,3-六氟-2-丙基、七氟-2-丙基、1-(溴甲基)-2-溴乙基、4-氟丁基、4-氯丁基、4-溴丁基或九氟丁基。
术语“C1-C4卤代烷氧基”是指经由在烷基的任意键处的氧键键接的具有1-4个碳原子的直链或支化烷基(如上所定义),其中这些基团中的一些或所有氢原子被如上所定义的卤素替换,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、二氯氟甲氧基、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或C3-C4卤代烷氧基,如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、2,2,3,3,3-五-氟丙氧基、七氟丙氧基、1-(氟甲基)-2-氟乙氧基、1-(氯甲基)-2-氯乙氧基、1-(溴甲基)-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。
术语“C1-C4卤代烷硫基”是指经由在烷基的任意键处的硫键键接的具有1-4个碳原子的直链或支化烷基(如上所定义),其中这些基团中的一些或所有氢原子被如上所定义的卤素替换,例如C1-C2卤代烷硫基,如氯甲硫基、溴甲硫基、二氯甲硫基、三氯甲硫基、氟甲硫基、二氟甲硫基、三氟甲硫基、氯氟甲硫基、二氯氟甲硫基、氯二氟甲硫基、1-氯乙硫基、1-溴乙硫基、1-氟-乙硫基、2-氟乙硫基、2,2-二氟乙硫基、2,2,2-三氟乙硫基、2-氯-2-氟乙硫基、2-氯-2,2-二氟乙硫基、2,2-二氯-2-氟乙硫基、2,2,2-三氯乙硫基和五氟乙硫基或C3-C4卤代烷硫基,如2-氟-丙硫基、3-氟丙硫基、2,2-二氟丙硫基、2,3-二氟丙硫基、2-氯-丙硫基、3-氯丙硫基、2,3-二氯丙硫基、2-溴丙硫基、3-溴-丙硫基、3,3,3-三氟丙硫基、3,3,3-三氯丙硫基、2,2,3,3,3-五氟丙硫基、七氟丙硫基、1-(氟甲基)-2-氟乙硫基、1-(氯甲基)-2-氯乙硫基、1-(溴甲基)-2-溴乙硫基、4-氟丁硫基、4-氯丁硫基、4-溴丁硫基或九氟丁硫基。
在式(I)的芳基甲酸联苯基酰胺中,优选其中变量在每种情况下具有如下所给含义的那些,在每种情况下单独或组合:
X 氟、氯或甲基,尤其是氟或甲基,非常特别优选氟;
Y 卤素、甲基、卤代甲基、甲氧基、卤代甲氧基、卤代乙氧基、甲硫基、卤代甲硫基或甲氧亚氨基甲基,更优选卤素、甲基、三氟甲基、甲氧基、二氟甲氧基、三氟甲氧基、四氟乙氧基、甲硫基、二氟甲硫基、三氟甲硫基、甲氧亚氨基甲基或烯丙氧亚氨基甲基,尤其是卤素、甲基、三氟甲基或三氟甲硫基,特别优选卤素、甲基、三氟甲基、三氟甲氧基、四氟乙氧基或三氟甲硫基,非常特别优选氟或氯;
m 0、1、2或3,更优选1、2或3,尤其是2或3;如果m为2或3,则基团Y可具有相同或不同含义;
n 0或1,尤其是0;
R1 甲基或卤代甲基,更优选甲基、氟甲基、二氟甲基、氯氟甲基或三氟甲基,尤其是卤代甲基,优选二氟甲基、氯氟甲基和三氟甲基,更优选二氟甲基和三氟甲基,特别优选二氟甲基;
R2 甲基;
R3 氢、氟或氯,尤其是氢;
R4 C1-C4烷基,尤其是甲基;
R5 甲基或卤代甲基,尤其是甲基、二氟甲基或三氟甲基,特别优选二氟甲基或三氟甲基;
R6 卤素、甲基或卤代甲基,尤其是氟、氯、碘、甲基、二氟甲基或三氟甲基,特别优选氯、碘或三氟甲基,特别是氯。
本发明的一个实施方案涉及其中X为甲基的式I化合物。
本发明的另一实施方案涉及其中Y为氟的式I化合物。
本发明的另一实施方案涉及其中Y为氯的式I化合物。
本发明的另一实施方案涉及其中m为0的式I化合物。
本发明的另一实施方案涉及其中m为1的式I化合物。
本发明的另一实施方案涉及其中n为1的式I化合物。
本发明的一个优选实施方案涉及式Ia化合物:
其中X、Y、m、n、R1、R2和R3如本文所定义且优选具有作为优选所述的含义。在化合物Ia中,优选其中m为0-3,优选1、2或3,更优选2或3,且n为0或1的那些。
进一步优选其中R3为氢的那些化合物Ia。
进一步优选其中R3为氟的那些化合物Ia。
进一步优选其中R3为氯的那些化合物Ia。
进一步优选其中R1为卤代甲基,优选CF3、CHF2或CHFCl,更优选CF3或CHF2,尤其是CHF2的那些化合物Ia。
进一步优选其中R2为甲基的那些化合物Ia。
进一步优选其中X为卤素,特别是氟的那些化合物Ia。
进一步优选其中Y为卤素,特别是氟或氯、甲基或SCF3,更优选氟或氯的那些化合物Ia。
非常特别优选下表1中所述的化合物Ia(R2为甲基,除化合物编号Ia.212外,其中R2为乙基):
表1
化合物 | R1 | R3 | Xn | Ym | 熔点[℃] |
Ia.1 | CH3 | Cl | --- | --- | 108-109 |
Ia.2 | CHF2 | H | --- | --- | 113-119 |
Ia.3 | CF3 | H | --- | --- | 147-148 |
Ia.4 | CF3 | H | --- | 4-Cl | 151-153 |
Ia.5 | CF3 | H | --- | 4-OCH3 | 152-154 |
Ia.6 | CF3 | H | --- | 4-F | 156-157 |
Ia.7 | CF3 | H | --- | 3-Cl | 92-94 |
Ia.8 | CF3 | H | --- | 2-CH3 | 119-122 |
Ia.9 | CH3 | H | --- | --- | 158-160 |
Ia.10 | CH3 | H | --- | 4-Cl | 165-166 |
Ia.11 | CH3 | H | --- | 4-OCH3 | 156-157 |
Ia.12 | CH3 | H | --- | 4-F | 175-176 |
Ia.13 | CH3 | H | --- | 3-Cl | 104-106 |
Ia.14 | CH3 | H | --- | 2-CH3 | 137-139 |
Ia.15 | Cl | H | --- | --- | 201-206 |
Ia.16 | CF3 | H | --- | 4-C(CH3)3 | 189-195 |
Ia.17 | CH3 | H | --- | 4-C(CH3)3 | 184-189 |
Ia.18 | CF3 | H | --- | 3-F | 115-120 |
Ia.19 | CF3 | H | --- | 4-CH(CH3)2 | 202-204 |
Ia.20 | CF3 | H | --- | 3-CH3 | 97-99 |
Ia.21 | CH3 | Cl | --- | 4-F | 147-152 |
Ia.22 | CH3 | Cl | --- | 4-Cl | 180-183 |
Ia.23 | CH3 | Cl | --- | 4-OCH3 | 135-143 |
Ia.24 | CF3 | H | 4-F | 4-F | 135-138 |
Ia.25 | CF3 | H | 4-F | 4-Cl | 136-140 |
Ia.26 | CF3 | H | 4-F | 4-CH3 | 148-151 |
Ia.27 | CH3 | H | 4-F | 4-F | 162-166 |
Ia.28 | CH3 | H | 4-F | 4-Cl | 160-164 |
Ia.29 | CH3 | H | 4-F | 4-CH3 | 154-157 |
Ia.30 | CF3 | H | 5-F | 4-F | 165-170 |
Ia.31 | CF3 | H | 3-F | 4-F | 124-126 |
化合物 | R1 | R3 | Xn | Ym | 熔点[℃] |
Ia.32 | CF3 | H | 3-F | 4-Cl | 127-128 |
Ia.33 | CH3 | F | --- | 4-Cl | 135-139 |
Ia.34 | CH3 | F | --- | 4-CH3 | 113-114 |
Ia.35 | CH3 | F | --- | 4-F | 138-139 |
Ia.36 | CH3 | F | --- | --- | 147-150 |
Ia.37 | CH3 | F | --- | 4-(CH=N-OCH3) | 123-124 |
Ia.38 | CF3 | H | --- | 3-Cl,4-Cl | 131-133 |
Ia.39 | CF3 | H | --- | 3-Cl,4-F | 133-134 |
Ia.40 | CF3 | H | --- | 2-Cl,4-Cl | 136-140 |
Ia.41 | CF3 | H | --- | 3-F,4-F | 126-128 |
Ia.42 | CF3 | H | --- | 3-Cl,5-Cl | 101-105 |
Ia.43 | CHF2 | H | --- | 3-Cl,5-Cl | 131-132 |
Ia.44 | CHF2 | H | --- | 3-Cl,4-F | 129-130 |
Ia.45 | CHF2 | H | --- | 3-F,4-F | 122-123 |
Ia.46 | CHF2 | H | --- | 3-Cl,4-Cl | 129-130 |
Ia.47 | CHF2 | H | --- | 2-Cl,4-Cl | 123-124 |
Ia.48 | CH3 | CH3 | --- | 4-Cl | 104-108 |
Ia.49 | CH3 | Cl | --- | 3-Cl,4-Cl | 104-108 |
Ia.50 | CH3 | Cl | --- | 2-Cl,4-Cl | 117-122 |
Ia.51 | CH3 | Cl | --- | 3-Cl,4-F | 134-137 |
Ia.52 | CH3 | Cl | --- | 3-Cl,5-Cl | 135-139 |
Ia.53 | CF3 | H | --- | 4-CH3 | 163-165 |
Ia.54 | CF3 | H | --- | 4-CF3 | 175-177 |
Ia.55 | CF3 | H | --- | 2-F,5-F | 110-112 |
Ia.56 | CF3 | H | --- | 2-CF3 | 120-121 |
Ia.57 | CF3 | H | --- | 2-F,4-Cl | 136-138 |
Ia.58 | CF3 | H | --- | 2-CH3,4-Cl | 130-131 |
Ia.59 | CF3 | H | --- | 3-CH3,4-Cl | 109-111 |
Ia.60 | CF3 | H | --- | 2-CH3,4-F | 125-126 |
Ia.61 | CF3 | H | --- | 3-CH3,4-F | 126-127 |
Ia.62 | CF3 | H | --- | 3-F,4-Cl | 149-150 |
Ia.63 | CF3 | H | --- | 2-F,4-F | 100-102 |
Ia.64 | CF3 | H | --- | 3-CF3 | 132-134 |
化合物 | R1 | R3 | Xn | Ym | 熔点[℃] |
Ia.65 | CF3 | H | --- | 4-CN | 200-201 |
Ia.66 | CF3 | H | --- | 2-F,4-OCH3 | 102-104 |
Ia.67 | CF3 | H | --- | 2-F,6-F | 141-143 |
Ia.68 | CHF2 | H | --- | 4-CF3 | 164-165 |
Ia.69 | CHF2 | H | --- | 3-CF3 | 124-125 |
Ia.70 | CHF2 | H | --- | 2-CF3 | 133-134 |
Ia.71 | CHF2 | H | --- | 2-F,5-F | 139-141 |
Ia.72 | CHF2 | H | --- | 2-F,4-F | 90-92 |
Ia.73 | CHF2 | H | --- | 2-F,4-Cl | 124-126 |
Ia.74 | CHF2 | H | --- | 3-F,4-Cl | 166-167 |
Ia.75 | CHF2 | H | --- | 2-CH3,4-F | 123-124 |
Ia.76 | CHF2 | H | --- | 3-CH3,4-F | 130-132 |
Ia.77 | CHF2 | H | --- | 2-CH3,4-Cl | 155-156 |
Ia.78 | CHF2 | H | --- | 3-CH3,4-Cl | 145-146 |
Ia.79 | CHF2 | H | --- | 4-CN | 214-216 |
Ia.80 | CHF2 | H | --- | 2-CH3,4-OCH3 | 84-86 |
Ia.81 | CHF2 | H | --- | 4-F | 153-155 |
Ia.82 | CHF2 | H | --- | 4-Cl | 158-160 |
Ia.83 | CF3 | H | --- | 2-F,4-Cl,5-OCH3 | |
Ia.84 | CF3 | H | --- | 2-F,4-Cl,5-CH3 | 106-108 |
Ia.85 | CF3 | H | --- | 3-F,4-F,5-F | 120-124 |
Ia.86 | CF3 | H | --- | 2-F,4-F,5-F | 110-113 |
Ia.87 | CHF2 | H | --- | 2-F,4-Cl,5-OCH3 | 150-152 |
Ia.88 | CF3 | H | --- | 2-F,3-F,4-F | 123-125 |
Ia.89 | CHF2 | H | --- | 2-F,4-Cl,5-CH3 | 120-122 |
Ia.90 | CHF2 | H | --- | 3-F,4-F,5-F | 113-116 |
Ia.91 | CHF2 | H | --- | 2-F,4-F,5-F | |
Ia.92 | CH3 | H | --- | 3-Cl,4-Cl | |
Ia.93 | CH3 | H | --- | 2-Cl,4-Cl | |
Ia.94 | CH3 | H | --- | 3-F,4-F | 140-143 |
Ia.95 | CH3 | H | --- | 3-Cl,4-F | 177-180 |
Ia.96 | CH3 | H | --- | 3-Cl,5-Cl | |
Ia.97 | CH3 | H | --- | 3-F,4-Cl | 181-186 |
化合物 | R1 | R3 | Xn | Ym | 熔点[℃] |
Ia.98 | CH3 | H | --- | 2-F,4-F | |
Ia.99 | CH3 | H | --- | 2-F,4-Cl | 122-125 |
Ia.100 | CH3 | H | --- | 4-CN | 147-151 |
Ia.101 | CF3 | H | 4-F,6-Cl | 2-Cl,4-Cl | |
Ia.102 | CHF2 | H | 4-F,6-Cl | 3-Cl,4-Cl | 147-152 |
Ia.103 | CHF2 | H | 4-F,6-Cl | 3-F,4-F | |
Ia.104 | CF3 | H | 5-F | 3-Cl,4-Cl | 155-158 |
Ia.105 | CF3 | H | 5-F | 3-F,4-F | 159-161 |
Ia.106 | CHF2 | H | 5-F | 3-Cl,4-Cl | 100-105 |
Ia.107 | CHF2 | H | 5-F | 3-F,4-F | |
Ia.108 | CF3 | H | 4-F | 3-Cl,4-Cl | 108-113 |
Ia.109 | CF3 | H | 4-F | 3-F,4-F | 127-133 |
Ia.110 | CHF2 | H | 4-F | 3-Cl,4-Cl | 141-143 |
Ia.111 | CHF2 | H | 4-F | 3-F,4-F | 136-141 |
Ia.112 | CF3 | H | 4-F | 2-Cl,4-Cl | 131-136 |
Ia.113 | CHF2 | H | 4-F | 2-Cl,4-Cl | 122-128 |
Ia.114 | CF2-Cl | H | --- | 4-F | 128-130 |
Ia.115 | CF2-Cl | H | --- | 4-Cl | 136-138 |
Ia.116 | CF2-Cl | H | --- | 3-Cl,4-Cl | 131-133 |
Ia.117 | CF2-Cl | H | --- | 3-Cl,4-F | 120-121 |
Ia.118 | CF2-Cl | H | --- | 3-F,4-F | 138-139 |
Ia.119 | CF2-Cl | H | --- | 3-Cl,5-Cl | 118-119 |
Ia.120 | CF2-Cl | H | --- | 2-Cl,4-Cl | 126-127 |
Ia.121 | CF3 | F | --- | 4-F | 141-143 |
Ia.122 | CF3 | F | --- | 4-Cl | 152-153 |
Ia.123 | CF3 | F | --- | 3-Cl,4-F | 159-160 |
Ia.124 | CF3 | F | --- | 3-Cl,5-Cl | 158-159 |
Ia.125 | CF3 | F | --- | 2-Cl,4-Cl | 132-134 |
Ia.126 | CF3 | F | --- | 3-Cl,4-Cl | 148-150 |
Ia.127 | CF3 | F | --- | 4-CN | 178-180 |
Ia.128 | CHF-Cl | H | --- | 4-Cl | 136-138 |
Ia.129 | CHF-Cl | H | --- | 4-F | 129-131 |
Ia.130 | CHF-Cl | H | --- | 3-Cl,4-Cl | 122-124 |
化合物 | R1 | R3 | Xn | Ym | 熔点[℃] |
Ia.131 | CHF-Cl | H | --- | 3-Cl,4-F | 85-87 |
Ia.132 | CHF-Cl | H | --- | 3-F,4-F | 137-138 |
Ia.133 | CHF-Cl | H | --- | 3-Cl,5-Cl | 100-102 |
Ia.134 | CHF-Cl | H | --- | 2-Cl,4-Cl | 142-144 |
Ia.135 | CH2F | H | --- | 4-Cl | 155-157 |
Ia.136 | CH2F | H | --- | 4-F | 145-147 |
Ia.137 | CH2F | H | --- | 3-Cl,4-Cl | 134-136 |
Ia.138 | CH2F | H | --- | 3-Cl,4-F | 133-134 |
Ia.139 | CH2F | H | --- | 3-F,4-F | 141-143 |
Ia.140 | CH2F | H | --- | 3-Cl,5-Cl | 135-137 |
Ia.141 | CH2F | H | --- | 2-Cl,4-Cl | 111-112 |
Ia.142 | CF(Cl2) | H | --- | 4-Cl | 155-156 |
Ia.143 | CF(Cl2) | H | --- | 4-F | 139-140 |
Ia.144 | CF(Cl2) | H | --- | 3-Cl,4-Cl | 145-146 |
Ia.145 | CF(Cl2) | H | --- | 3-Cl,4-F | 70-71 |
Ia.146 | CF(Cl2) | H | --- | 3-F,4-F | 123-124 |
Ia.147 | CF(Cl2) | H | --- | 3-Cl,5-Cl | 107-108 |
Ia.148 | CF(Cl2) | H | --- | 2-Cl,4-Cl | 121-123 |
Ia.149 | CF3 | H | 4-CH3 | 3-Cl,4-Cl | 155-160 |
Ia.150 | CF3 | H | 4-CH3 | 2-Cl,4-Cl | 167-172 |
Ia.151 | CF3 | H | 4-CH3 | 3-F,4-F | 137-142 |
Ia.152 | CHF2 | H | 4-CH3 | 3-Cl,4-Cl | 95-98 |
Ia.153 | CHF2 | H | 4-CH3 | 2-Cl,4-Cl | 165-170 |
Ia.154 | CHF2 | H | 4-CH3 | 3-F,4-F | 148-152 |
Ia.155 | CF3 | H | 5-F | 2-Cl,4-Cl | 127-131 |
Ia.156 | CHF2 | H | 5-F | 2-Cl,4-Cl | 122-128 |
Ia.157 | CF3 | H | --- | 3-(OCH3) | |
Ia.158 | CF3 | H | 6-F | 3-Cl,4-Cl | 67-72 |
Ia.159 | CF3 | H | 6-F | 2-Cl,4-Cl | 142-146 |
Ia.160 | CHF2 | H | 6-F | 3-Cl,4-Cl | 152-155 |
Ia.161 | CHF2 | H | 6-F | 2-Cl,4-Cl | 133-137 |
Ia.162 | CF3 | H | 6-F | 3-F,4-F | 189-191 |
Ia.163 | CHF2 | H | 6-F | 3-F,4-F | 184-186 |
化合物 | R1 | R3 | Xn | Ym | 熔点[℃] |
Ia.164 | CF3 | H | --- | 3-CN | 76-78 |
Ia.165 | CF3 | H | --- | 3-NO2 | 84-87 |
Ia.166 | CF3 | H | --- | 4-NO2 | 184-185 |
Ia.167 | CF3 | H | --- | 2-(OCH3) | 117-118 |
Ia.168 | CF3 | H | --- | 3-(OCHF2) | |
Ia.169 | CF3 | H | --- | 4-(OCHF2) | 174-175 |
Ia.170 | CF3 | H | --- | 4-(OCF3) | 194-196 |
Ia.171 | CF3 | H | --- | 4-(OCF2-CHF2) | 185-186 |
Ia.172 | CF3 | H | --- | 3-(SCF3) | 56-59 |
Ia.173 | CF3 | H | --- | 4-(SCF3) | 173-174 |
Ia.174 | CF3 | H | --- | 2-SCH3 | 134-135 |
Ia.175 | CF3 | H | --- | 3-SCH3 | 94-96 |
Ia.176 | CF3 | H | --- | 4-SCH3 | 195-196 |
Ia.177 | CF3 | H | --- | 3-CH3,5-CH3 | |
Ia.178 | CF3 | H | --- | 3-NO2,4-Cl | |
Ia.179 | CF3 | H | --- | 3-CF3,5-CF3 | |
Ia.180 | CF3 | H | --- | 3-F,5-CF3 | |
Ia.181 | CF3 | H | --- | 3-CH3,4-CH3 | |
Ia.182 | CF3 | H | --- | 3-CF3,4-Cl | |
Ia.183 | CF3 | H | --- | 3-CF3,4-NO2 | |
Ia.184 | CF3 | H | --- | 3-CH3,4-OCH3 | |
Ia.185 | CF3 | H | --- | 3-OCH3,4-OCH3 | |
Ia.186 | CF3 | H | --- | 3-F,4-OCH3 | |
Ia.187 | CF3 | H | --- | 3-OCH3,4-Cl | |
Ia.188 | CH3 | H | 4-F | 3-Cl,4-Cl | 156-157 |
Ia.189 | CF3 | H | --- | 3-F,4-(CH=N-OCH3) | 180-182 |
Ia.190 | CHF2 | H | --- | 3-F,4-(CH=N-OCH3) | 180-182 |
Ia.191 | CF3 | H | --- | 3-Cl,4-CH3 | |
Ia.192 | CF3 | H | --- | 2-Cl,5-CF3 | |
Ia.193 | CF3 | H | --- | 3-CF3,4-F | |
Ia.194 | CF3 | H | --- | 2-OCH3,5-F |
化合物 | R1 | R3 | Xn | Ym | 熔点[℃] |
Ia.195 | CF3 | H | --- | 2-F,5-CH3 | |
Ia.196 | CF3 | H | --- | 2-Cl,5-NO2 | |
Ia.197 | CF3 | H | --- | 2-CH3,5-Cl | |
Ia.198 | CF3 | H | --- | 2-F,4-CH3 | |
Ia.199 | CF3 | H | --- | 2-CH3,4-NO2 | |
Ia.200 | CF3 | H | --- | 2-CH3,4-CH3 | |
Ia.201 | CF3 | H | --- | 2-CH3,4-OC2H5 | |
Ia.202 | CF3 | H | --- | 2-NO2,4-Cl | |
Ia.203 | CF3 | H | --- | 2-NO2,4-CH3 | |
Ia.204 | CF3 | H | --- | 2-NO2,4-OCH3 | |
Ia.205 | CF3 | H | --- | 2-NO2,4-NO2 | |
Ia.206 | CF3 | H | --- | 2-CH3,4-OCH3 | |
Ia.207 | CF3 | H | --- | 2-CH3,3-CH3 | |
Ia.208 | CF3 | H | --- | 2-CH3,3-NO2 | |
Ia.209 | CH2F | H | --- | 3-F,4-F,5-F | 152-156 |
Ia.210 | CF2-Cl | H | --- | 3-F,4-F,5-F | 158-161 |
Ia.211 | CHF-Cl | H | --- | 3-F,4-F,5-F | 154-157 |
Ia.212 | CHF2 | H | --- | 3-F,4-F,5-F | 156-159 |
Ia.213 | CF3 | H | --- | 2-NO2 | 118-119 |
Ia.214 | CF3 | H | --- | 3-CN,4-OCH3 | 184-187 |
Ia.215 | CHF2 | H | --- | 3-CN,4-OCH3 | 152-154 |
Ia.216 | CF3 | H | --- | 3-OCH3,4-CN | 234-236 |
Ia.217 | CHF2 | H | --- | 3-OCH3,4-CN | 188-190 |
Ia.218 | CF3 | F | --- | 4-CF3 | 170-173 |
Ia.219 | CH3 | Cl | --- | 4-CF3 | 173-175 |
Ia.220 | CH3 | H | --- | 4-CF3 | 174-177 |
Ia.221 | CH2F | H | --- | 4-CF3 | 156-158 |
Ia.222 | CF2-Cl | H | --- | 4-CF3 | 193-196 |
Ia.223 | CHF-Cl | H | --- | 4-CF3 | 118-186 |
Ia.224 | CH2F | H | --- | --- | 179-181 |
Ia.225 | CH2F | H | --- | 3-F,4-Cl | 172-174 |
Ia.226 | CH2F | H | --- | 2-F,4-Cl | 111-114 |
Ia.227 | CH2F | H | --- | 2-F,3-F,4-F | 126-129 |
化合物 | R1 | R3 | Xn | Ym | 熔点[℃] |
Ia.228 | CH2F | H | --- | 2-F,4-F,5-F | 133-136 |
Ia.229 | CHF2 | H | --- | 2-F,3-F,4-F | 138-140 |
Ia.230 | CH2F | H | --- | 3-Cl | 96-99 |
Ia.231 | CHF2 | H | --- | 3-Cl | 110-112 |
Ia.232 | CH2F | H | --- | 2-Cl | 162-165 |
Ia.233 | CHF2 | H | --- | 2-Cl | 170-173 |
Ia.234 | CF3 | H | --- | 2-Cl | 135-139 |
Ia.235 | CH2F | H | --- | 3-F | 138-141 |
Ia.236 | CHF2 | H | --- | 3-F | 130-135 |
Ia.237 | CH2F | H | --- | 2-F | 169-173 |
Ia.238 | CF3 | H | --- | 2-F | 150-154 |
Ia.239 | CH2F | H | --- | 2-F,4-F | 100-102 |
Ia.240 | CH2F | H | --- | 2-Cl,4-F | 104-106 |
Ia.241 | CHF2 | H | --- | 2-Cl,4-F | 120-124 |
Ia.242 | CF3 | H | --- | 2-Cl,4-F | 128-131 |
Ia.243 | CH2F | H | --- | 3-F,5-F | 111-115 |
Ia.244 | CHF2 | H | --- | 3-F,5-F | 125-127 |
Ia.245 | CF3 | H | --- | 3-F,5-F | 142-146 |
Ia.246 | CHF2 | H | --- | 2-F | 166-169 |
Ia.247 | CHF2 | H | 4-F | 3-Cl,4-F | 137-138 |
Ia.248 | CHF2 | H | 5-F | 3-Cl,4-F | 149-151 |
Ia.249 | CHF2 | H | 6-F | 3-Cl,4-F | 181-182 |
Ia.250 | CHF2 | H | --- | 3-Cl,5-F | 114-118 |
Ia.251 | CF3 | H | --- | 3-Cl,5-F | 101-103 |
Ia.252 | CH2F | H | --- | 3-Cl,5-F | 97-100 |
Ia.253 | CH2F | H | --- | 2-Cl,5-Cl | 123-125 |
Ia.254 | CHF2 | H | --- | 2-Cl,5-Cl | 130-132 |
Ia.255 | CF3 | H | --- | 2-Cl,5-Cl | 131-135 |
Ia.256 | CH2F | H | --- | 2-F,5-Cl | 137-139 |
Ia.257 | CHF2 | H | --- | 2-F,5-Cl | 148-150 |
Ia.258 | CF3 | H | --- | 2-F,5-Cl | 117-120 |
Ia.259 | CH2F | H | --- | 2-F,6-F | 168-172 |
Ia.260 | CHF2 | H | --- | 2-F,6-F | 129-132 |
化合物 | R1 | R3 | Xn | Ym | 熔点[℃] |
Ia.261 | CH2F | H | --- | 2-Cl,6-F | 127-130 |
Ia.262 | CHF2 | H | --- | 2-Cl,6-F | 118-122 |
Ia.263 | CF3 | H | --- | 2-Cl,6-F | 116-119 |
Ia.264 | CH2F | H | --- | 2-Cl,5-F | |
Ia.265 | CHF2 | H | --- | 2-Cl,5-F | 118-120 |
Ia.266 | CF3 | H | --- | 2-Cl,5-F | |
Ia.267 | CHF2 | H | --- | 2-Cl,6-Cl | 148-150 |
Ia.268 | CF3 | H | --- | 2-Cl,6-Cl | 135-137 |
Ia.269 | CH2F | H | --- | 2-Cl,6-Cl | 137-139 |
Ia.270 | CF3 | H | --- | 2-C2H5 | 105-108 |
Ia.271 | CF3 | H | --- | 3-F,4-CH3 | 139-141 |
Ia.272 | CF3 | H | --- | 2-OC2H5 | 100-103 |
Ia.273 | CF3 | H | --- | 2-(OCH2-C2H5) | 84-86 |
Ia.274 | CF3 | H | --- | 2-(OCH2CH2-C2H5) | 81-83 |
Ia.275 | CF3 | H | --- | 2-[OCH(CH3)2] | 86-89 |
Ia.276 | CHF2 | H | --- | 2-C2H5 | 108-110 |
Ia.277 | CH3 | F | --- | 2-CH3 | 108-110 |
Ia.278 | CH3 | F | --- | 2-NO2 | 148-151 |
Ia.279 | CH3 | F | --- | 2-Cl | 107-111 |
Ia.280 | CH3 | F | --- | 2-CF3 | 110-112 |
Ia.281 | CH3 | F | --- | 2-F,4-CH3 | 123-126 |
Ia.282 | CH3 | F | --- | 2-CH3,4-Cl | 132-136 |
Ia.283 | CH3 | F | -- | 2-CH3,4-F | 146-149 |
Ia.284 | CH3 | F | --- | 2-F,4-OCH3 | 130-132 |
Ia.285 | CH3 | F | --- | 2-F,4-Cl | 133-136 |
Ia.286 | CH3 | F | --- | 2-F,5-CN | 143-145 |
Ia.287 | CH3 | F | --- | 2-F,5-OCH3 | 94-97 |
Ia.288 | CH3 | F | --- | 2-F,5-Cl | 100-102 |
Ia.289 | CH3 | F | --- | 2-Cl,5-Cl | 123-124 |
Ia.290 | CH3 | F | --- | 2-CH3,5-NO2 | 117-118 |
Ia.291 | CH3 | F | --- | 2-CH3,5-CH3 | 96-97 |
Ia.292 | CH3 | F | --- | 3-CF3,5-CF3 | 156-158 |
Ia.293 | CH3 | F | --- | 3-F,5-CH3 | 116-117 |
化合物 | R1 | R3 | Xn | Ym | 熔点[℃] |
Ia.294 | CH3 | F | --- | 3-F,5-CN | 168-170 |
Ia.295 | CH3 | F | --- | 3-CH3,5-CH3 | 152-154 |
Ia.296 | CH3 | F | --- | 3-CN | 137-138 |
Ia.297 | CH3 | F | --- | 3-NO2 | 137-139 |
Ia.298 | CH3 | F | --- | 3-CF3 | 113-114 |
Ia.299 | CF3 | H | --- | 2-OCH3,4-F | 120-121 |
Ia.300 | CF3 | H | --- | 3-NO2,4-OCH3 | 170-172 |
Ia.301 | CF3 | H | --- | 3-Cl,4-OCH3 | 140-145 |
Ia.302 | CF3 | H | --- | 2-F,5-OCH3 | 128-129 |
Ia.303 | CF3 | H | --- | 2-OCH3,5-[CH(CH3)2] | 127-129 |
Ia.304 | CH3 | H | --- | 2-CHF2 | 134-135 |
Ia.305 | CHF2 | H | --- | 2-CHF2 | 131-133 |
Ia.306 | CF3 | F | --- | 2-CHF2 | 126-128 |
Ia.307 | CF3 | F | --- | 2-C2H5 | 110-112 |
Ia.308 | CH3 | H | --- | 2-C2H5 | 116-118 |
Ia.309 | CF3 | F | --- | 2-CH3 | 111-112 |
Ia.310 | CF3 | F | --- | 2-OCH3 | 121-123 |
Ia.311 | CHF2 | H | --- | 2-OCH3 | 97-99 |
Ia.312 | CH3 | H | --- | 2-OCH3 | 94-96 |
Ia.313 | CHF2 | H | --- | 4-(SCF3) | 134-137 |
在上述化合物Ia中,优选化合物Ia.43、Ia.44、Ia.45、Ia.57、Ia.64、Ia.84、Ia.85、Ia.90、Ia.110、Ia.173、Ia.211、Ia.219、Ia.230、Ia.231、Ia.233、Ia.244、Ia.245、Ia.249、Ia.250、Ia.251、Ia.255和Ia.313。更优选化合物Ia.85、Ia.90、Ia.110、Ia.245和Ia.255。特别优选化合物Ia为化合物Ia.90和Ia.110。
本发明的另一实施方案涉及式Ib化合物:
其中X、Y、m、n、R1、R2和R3如上所定义。在化合物Ib中,优选其中m为0-3且n为0或1的那些。非常特别优选描述于下表2中的化合物Ib:
表2
化合物 | R4 | R5 | Xn | Ym | 熔点[℃] |
Ib.1 | CH3 | CF3 | --- | --- | 116-118 |
Ib.2 | CH3 | CH3 | --- | --- | 136-137 |
Ib.3 | H | CH3 | --- | --- | 66-68 |
Ib.4 | H | CF3 | --- | --- | 102-106 |
Ib.5 | CH3 | CH3 | --- | 4-Cl | 119-122 |
Ib.6 | CH3 | CH3 | --- | 4-OCH3 | 92-94 |
Ib.7 | CH3 | CH3 | --- | 2-OCH3 | 90-91 |
Ib.8 | CH3 | CF3 | --- | 4-OCH3 | 83-86 |
Ib.9 | CH3 | CF3 | --- | 4-Cl | 122-125 |
Ib.10 | CH3 | CF3 | --- | 2-OCH3 | |
Ib.11 | CH3 | CF3 | --- | 4-F | 112-114 |
Ib.12 | CH3 | CF3 | --- | 2-CH3 | |
Ib.13 | CH3 | CF3 | --- | 3-Cl | 137-139 |
Ib.14 | CH3 | CH3 | --- | 4-F | 122-124 |
Ib.15 | CH3 | CH3 | --- | 2-CH3 | |
Ib.16 | CH3 | CH3 | --- | 3-Cl | |
Ib.17 | CH3 | CF2-Cl | --- | --- | 143-145 |
Ib.18 | CH3 | CHF2 | --- | --- | 84-86 |
Ib.19 | CH3 | CF3 | --- | 3-CH3 | |
Ib.20 | CH3 | CF3 | --- | 3-F | 94-95 |
Ib.21 | CH3 | CF3 | --- | 4-CH3 | 76-79 |
Ib.22 | CH3 | CF3 | --- | 4-CH(CH3)2 | 165-166 |
Ib.23 | CH3 | CF3 | --- | 4-C(CH3)3 | 169-170 |
Ib.24 | CH3 | CH3 | --- | 4-C(CH3)3 | 151-153 |
Ib.25 | CH3 | CF3 | 4-F | 4-F | 136-138 |
Ib.26 | CH3 | CF3 | 4-F | 4-CH3 | 106-108 |
Ib.27 | CH3 | CF3 | 4-F | 4-Cl | 144-146 |
Ib.28 | CH3 | CF3 | 4-F | --- | 146-148 |
Ib.29 | CH3 | CF3 | 5-F | 4-F | 108-110 |
Ib.30 | CH3 | CF3 | 3-F | 4-F | 118-120 |
化合物 | R4 | R5 | Xn | Ym | 熔点[℃] |
Ib.31 | CH3 | CF3 | 3-F | 4-Cl | 123-124 |
Ib.32 | CH3 | CF3 | --- | 2-Cl,4-Cl | 111-115 |
Ib.33 | CH3 | CF3 | --- | 3-Cl,4-F | 112-115 |
Ib.34 | CH3 | CF3 | --- | 3-Cl,4-Cl | 100-102 |
Ib.35 | CH3 | CF3 | --- | 3-F,4-F | 121-123 |
Ib.36 | CH3 | CF3 | --- | 3-Cl,5-Cl | 126-128 |
Ib.37 | CH3 | CHF2 | --- | 2-Cl,4-Cl | 101-104 |
Ib.38 | CH3 | CHF2 | --- | 3-Cl,5-Cl | |
Ib.39 | CH3 | CHF2 | --- | 3-F,4-F | 81-84 |
Ib.40 | CH3 | CHF2 | --- | 3-Cl,4-Cl | |
Ib.41 | CH3 | CHF2 | --- | 3-Cl,4-F | |
Ib.42 | CH3 | CF3 | --- | 3-CH3,5-CH3 | |
Ib.43 | CH3 | CF3 | --- | 3-NO2,4-Cl | |
Ib.44 | CH3 | CF3 | --- | 3-CF3,5-CF3 | |
Ib.45 | CH3 | CF3 | --- | 3-F,5-CF3 | |
Ib.46 | CH3 | CF3 | 5-F | 2-F,4-Cl,5-OCH3 | |
Ib.47 | CH3 | CHF2 | 5-F | 2-F,4-Cl,5-OCH3 | 134-137 |
Ib.48 | CH3 | CH3 | 5-F | 2-F,4-Cl,5-OCH3 | |
Ib.49 | CH3 | CF3 | 4-F,6-Cl | 2-F,4-Cl,5-CH3 | 150-153 |
Ib.50 | CH3 | CHF2 | 4-F,6-Cl | 2-F,4-Cl,5-CH3 | 154-157 |
Ib.51 | CH3 | CH3 | 4-F,6-Cl | 2-F,4-Cl,5-CH3 | |
Ib.52 | CH3 | CF3 | 5-F | 3-F,4-F | 112-116 |
Ib.53 | CH3 | CHF2 | 5-F | 3-F,4-F | 120-122 |
Ib.54 | CH3 | CH3 | 5-F | 3-F,4-F | |
Ib.55 | CH3 | CF3 | 4-F,6-Cl | 3-F,4-F | |
Ib.56 | CH3 | CHF2 | 4-F,6-Cl | 3-F,4-F | |
Ib.57 | CH3 | CH3 | 4-F,6-Cl | 3-F,4-F | 170-174 |
Ib.58 | CH3 | CF3 | --- | 3-F,4-F,5-F | 148-152 |
Ib.59 | CH3 | CF3 | --- | 2-F,4-F,5-F | 112-116 |
Ib.60 | CH3 | CH3 | --- | 3-F,4-F,5-F | 123-128 |
Ib.61 | CH3 | CH3 | --- | 2-F,4-F,5-F | 150-154 |
Ib.62 | CH3 | CF3 | --- | 3-CF3 4-NO2 | |
Ib.63 | CH3 | CF3 | --- | 3-CH3,4-OCH3 |
化合物 | R4 | R5 | Xn | Ym | 熔点[℃] |
Ib.64 | CH3 | CF3 | --- | 3-OCH3,4-OCH3 | |
Ib.65 | CH3 | CF3 | --- | 3-F,4-OCH3 | |
Ib.66 | CH3 | CHF2 | --- | 4-CF3 | 145-147 |
Ib.67 | CH3 | CHF2 | --- | 3-F,4-Cl | 112-114 |
Ib.68 | CH3 | CHF2 | --- | 4-Cl | 147-149 |
Ib.69 | CH3 | CF3 | --- | 3-F,4-Cl | 143-144 |
Ib.70 | CH3 | CHF2 | --- | 4-Br | 152-153 |
Ib.71 | CH3 | CF3 | --- | 3-Cl,4-CH3 | |
Ib.72 | CH3 | CF3 | --- | 3-CH3,4-Cl | |
Ib.73 | CH3 | CF3 | --- | 3-CH3,4-F | |
Ib.74 | CH3 | CF3 | --- | 3-CF3,4-F | |
Ib.75 | CH3 | CF3 | --- | 2-F,4-CH3 | |
Ib.76 | CH3 | CF3 | --- | 2-CH3,4-NO2 | |
Ib.77 | CH3 | CF3 | --- | 2-CH3,4-CH3 | |
Ib.78 | CH3 | CF3 | --- | 2-CH3,4-OC2H5 | |
Ib.79 | CH3 | CF3 | --- | 2-NO2,4-Cl | |
Ib.80 | CH3 | CF3 | --- | 2-NO2,4-OCH3 | |
Ib.81 | CH3 | CF3 | --- | 2-NO2,4-NO2 | |
Ib.82 | CH3 | CF3 | --- | 3-CN | 138-140 |
Ib.83 | CH3 | CF3 | --- | 4-CN | 169-171 |
Ib.84 | CH3 | CF3 | --- | 3-NO2 | 136-140 |
Ib.85 | CH3 | CF3 | --- | 4-NO2 | 199-201 |
Ib.86 | CH3 | CF3 | --- | 3-OCH3 | 92-93 |
Ib.87 | CH3 | CF3 | --- | 3-OCHF2 | 85-86 |
Ib.88 | CH3 | CF3 | --- | 4-OCHF2 | 119-120 |
Ib.89 | CH3 | CF3 | --- | 4-OCF3 | 148-149 |
Ib.90 | CH3 | CF3 | --- | 3-OCF3 | 82-84 |
Ib.91 | CH3 | CF3 | --- | 4-OCF2-CHF2 | 147-148 |
Ib.92 | CH3 | CF3 | --- | 3-SCF3 | 125-126 |
Ib.93 | CH3 | CF3 | --- | 4-SCF3 | 138-140 |
Ib.94 | CH3 | CF3 | --- | 2-SCH3 | |
Ib.95 | CH3 | CF3 | --- | 3-SCH3 | 104-105 |
Ib.96 | CH3 | CF3 | --- | 4-SCH3 | 141-142 |
化合物 | R4 | R5 | Xn | Ym | 熔点[℃] |
Ib.97 | CH3 | CF3 | --- | 2-NO2 | 120-121 |
Ib.98 | CH3 | CF3 | --- | 3-CN,4-OCH3 | 183-184 |
Ib.99 | CH3 | CF3 | --- | 3-OCH3,4-CN | 150-152 |
本发明的另一实施方案涉及式Ic的化合物:
其中X、Y、m、n、R1、R2和R3如本文中所定义。在化合物Ic中优选其中m为0-3和n为0或1的那些。非常特别优选下表3所述的化合物Ic:
表3
化合物 | R6 | Xn | Ym | 熔点[℃] |
Ic.1 | Cl | --- | 2-OCH3 | |
Ic.2 | 碘 | --- | 3-Cl,4-Cl | 141-144 |
Ic.3 | 碘 | --- | 3-F,4-F | 113-117 |
Ic.4 | CF3 | --- | 3-Cl,4-Cl | 108-111 |
Ic.5 | CF3 | --- | 3-Cl,4-F | 100-103 |
本发明的另一实施方案涉及式Id的化合物:
其中X、Y、m、n、R1、R2和R3如本文所定义。在化合物Id中,优选其中m为0-3,优选1-3,更优选1或2,尤其是1且n为0或1的那些。非常特别优选下表4中所述的化合物Id:
表4
化合物 | R6 | Xn | Ym | 熔点[℃] |
Id.1 | Cl | --- | 4-Cl | 147-148 |
Id.2 | Cl | --- | 3-Cl,4-Cl | 125-127 |
Id.3 | Cl | --- | 3-Cl,5-Cl | 147-149 |
Id.4 | Cl | --- | 3-Cl,4-F | 144-145 |
化合物 | R6 | Xn | Ym | 熔点[℃] |
Id.5 | Cl | --- | 3-F,4-F | 123-125 |
Id.6 | Cl | --- | 2-Cl,4-Cl | 105-109 |
Id.7 | CF3 | --- | 3-Cl,4-Cl | 150-153 |
Id.8 | Cl | --- | 2-F,5-F | 74-75 |
Id.9 | Cl | --- | 2-F,4-Cl | 124-126 |
Id.10 | Cl | --- | 2-CH3,4-Cl | 122-123 |
Id.11 | Cl | --- | 3-CH3,4-Cl | 111-113 |
Id.12 | Cl | --- | 2-CH3,4-F | 95-97 |
Id.13 | Cl | --- | 3-CH3,4-F | 92-93 |
Id.14 | Cl | --- | 3-F,4-Cl | 113-115 |
Id.15 | Cl | --- | 2-F,4-F | 117-118 |
Id.16 | Cl | --- | 4-CN | 172-174 |
Id.17 | Cl | --- | 2-F,4-OCH3 | 110-112 |
Id.18 | Cl | 5-F | 2-Cl,4-Cl | 150-155 |
Id.19 | Cl | --- | 3-F,4-F,5-F | 139-144 |
Id.20 | Cl | --- | 2-F,4-F,5-F | 103-110 |
Id.21 | Cl | --- | 2-F,4-Cl,5-(OCH3) | 159-162 |
Id.22 | CF3 | 5-F | 2-Cl,4-Cl | 164-169 |
Id.23 | CF3 | --- | 3-F,4-F,5-F | 164-168 |
Id.24 | CF3 | --- | 2-F,4-F,5-F | 141-144 |
Id.25 | CF3 | --- | 2-F,4-Cl,5-(OCH3) | 151-156 |
Id.26 | CF3 | --- | 3-F,4-F | 121-125 |
Id.27 | CF3 | --- | 3-Cl,5-Cl | 161-165 |
Id.28 | CF3 | --- | 2-Cl,4-Cl | 143-147 |
Id.29 | CF3 | --- | 4-F,5-Cl | 167-170 |
Id.30 | Cl | --- | 3-NO2,4-Cl | |
Id.31 | Cl | --- | 3-CF3,5-CF3 | |
Id.32 | Cl | --- | 3-F,5-CF3 | |
Id.33 | Cl | --- | 3-CH3,4-CH3 | |
Id.34 | Cl | --- | 3-CF3,4-NO2 | |
Id.35 | Cl | --- | 3-CH3,4-OCH3 | |
Id.36 | Cl | --- | 3-OCH3,4-OCH3 | |
Id.37 | Cl | --- | 3-CH3,4-OH |
化合物 | R6 | Xn | Ym | 熔点[℃] |
Id.38 | Cl | --- | 3-F,4-OCH3 | |
Id.39 | CF3 | --- | 4-CF3 | 148-151 |
Id.40 | CF3 | --- | 3-CF3 | 124-127 |
Id.41 | CF3 | --- | 2-CF3 | 170-173 |
Id.42 | Cl | --- | 3-CF3 | 140-142 |
Id.43 | Cl | --- | 2-CF3 | 109-112 |
Id.44 | Cl | --- | 3-Cl,4-CH3 | |
Id.45 | Cl | --- | 2-NO2,4-Cl | |
Id.46 | Cl | --- | 2-NO2,4-NO2 | |
Id.47 | CF3 | --- | --- | 138-148 |
Id.48 | Cl | --- | 3-CN | 164-166 |
Id.49 | Cl | --- | 3-NO2 | 152-154 |
Id.50 | Cl | --- | 4-NO2 | 196-198 |
Id.51 | Cl | --- | 3-OCH3 | 84-86 |
Id.52 | Cl | --- | 3-OCHF2 | 125-127 |
Id.53 | Cl | --- | 4-OCHF2 | 135-139 |
Id.54 | Cl | --- | 3-OCF3 | 130-131 |
Id.55 | Cl | --- | 4-OCF3 | 162-163 |
Id.56 | Cl | --- | 4-OCF2-CHF2 | 118-120 |
Id.57 | Cl | --- | 3-SCF3 | 147-149 |
Id.58 | Cl | --- | 4-SCF3 | 145-149 |
Id.59 | Cl | --- | 2-SCH3 | 118-120 |
Id.60 | Cl | --- | 3-SCH3 | 90-92 |
Id.61 | Cl | --- | 4-SCH3 | 152-153 |
Id.62 | Cl | --- | 2-NO2 | 124-129 |
Id.63 | Cl | --- | 3-CN,4-OCH3 | 188-190 |
Id.64 | Cl | --- | 3-OCH3,4-CN | 154-155 |
特别优选的化合物Id为化合物Id.1、Id.55、Id.56和Id.58,其中更优选Id.1。
在化合物I中,优选其中Ar为基团IIa或IIc,其中Z优选为N的那些。更优选化合物Ia,其中特别优选化合物Ia.43、Ia.44、Ia.45、Ia.57、Ia.64、Ia.84、Ia.85、Ia.90、Ia.110、Ia.173、Ia.211、Ia.219、Ia.230、Ia.231、Ia.233、Ia.244、Ia.245、Ia.249、Ia.250、Ia.251、Ia.255和Ia.313,更优选化合物Ia.85、Ia.90、Ia.110、Ia.245和Ia.255,甚至更优选化合物Ia.90和Ia.110,其中在化合物Id中,特别优选化合物Id.1、Id.55、Id.56和Id.58,特别是Id.1。
如本文所用的术语“种子”是指从植物的生长阶段物理脱离和/或可长时间储存和/或可用于再生长相同物种的另一植物个体的植物的任何休眠阶段。
此处,术语“休眠”是指其中植物尽管不存在对植物生长(即非种子)状态关键的光、水和/或营养品而在合理的限度内保持发育能力的状态。该术语尤其指真正种子,而不包括植物繁殖体如吸根、球根、鳞茎、果实、块茎、伐条(cutting)和插条(cut shoot)。
如本文所用的术语“植物”是指整个植物或其部分。术语“整个植物”是指在植物生长中,即非种子阶段的完整的植物个体,其特征在于存在根、茎干和叶,以及取决于植物发育阶段的花和/或果实的排列,它们全部物理连接形成个体,该个体在合理条件下能无需人工措施而存活。该术语也可指直接收获的整个植物。
术语“植物部分”是指根、茎干、叶、花或植物生长阶段的其它部分,当它们从剩余部分脱落和分离时不能存活,除非有人工手段支持或可再长出失去部分以形成整个植物。用于本文的果实也认为是植物部分。
如本文所用的术语“根”是指为了实现它们的生理功能而通常位于土壤表面以下的植物部分。优选该术语是指在种子下面并且直接从种子或从其它根长出,而不是从茎干或叶长出的植物部分。
如本文所用的植物的“茎干和叶”应理解为指在种子萌发之后的茎干、干、枝、叶以及干和枝的其它附属部分,但不包括植物的根。优选植物的“茎干和叶”应理解为指由种子长出且与它们长出的种子相距至少1英寸距离的植物的那些非根部分(在种子外部区域),更优选指在土壤表面或以上的植物的非根部分。
如本文所用的“果实”认为是含有种子和/或用于播种,和/或可从植物上除去而不损害其生存能力的植物部分。
根据本发明,种子处理包括向种子施用式(I)的芳基甲酸联苯基酰胺。种子可来自天然出现的植物、来自借助经典育种而得到的植物或来自基因改性植物如耐受草甘膦(glyphosate)的大豆植物。
尽管本方法可适用于任何生理阶段的种子,优选种子处于足够持久的状态,不会在处理过程中招致显著损害。通常而言,种子为从田间收获;从植物上除去;和/或从果实和任何棒(cob)、荚、茎、外壳和周围的浆或其它非种子植物材料分离的种子。还优选种子生理稳定至处理不会对种子造成生理损害的程度。在一个实施方案中,例如处理可施用于已经收获、清洁并干燥至水分含量低于约15重量%的种子。在替代实施方案中,种子可以是已经干燥,然后涂水和/或其它材料,然后在用式(I)的芳基甲酸联苯基酰胺处理之前或过程中再干燥的种子。
在另一实施方案中,种子可以是来自基因改性植物,尤其是大豆植物的种子。
术语种子处理包括本领域已知的所有合适的种子处理,特别是拌种技术,如种子包衣(如种子造粒)、种子撒粉和种子吸取(如种子浸泡)。此处,“种子处理”是指使种子和式(I)的芳基甲酸联苯基酰胺相互接触的所有方法,“拌种”是指向种子提供一定量式(I)的芳基甲酸联苯基酰胺的种子处理方法,即该方法产生包含式(I)的芳基甲酸联苯基酰胺的种子。原则上,处理可施用于从种子收获至种子播种的任何时间的种子。种子例如可使用“播种箱”方法紧邻种植种子之前或种植种子的过程中处理。然而,处理也可在种植种子之前数周或数月,例如至多12个月,例如以拌种处理的形式进行处理,而没有观察到效力的显著降低。
有利的是将处理施用于未播种的种子。如本文所用的术语“未播种种子”意味着包括从种子收获到将种子播种到地面以使植物萌发和生长的任何时间中的种子。
当提及“处理”未播种种子时,该处理并不意味着包括其中将杀真菌剂施用于土壤,而不是直接施用于种子的那些措施。事实上,据信处理向其中播种种子的土壤,或更一般的生长介质赋予由种子生长的植物相同的保护作用:不希望限制于理论,推测芳基甲酸联苯基酰胺I对由根据本发明处理的种子生长的植物的预防作用至少部分基于活性化合物从播种种子迁移到周围的生长介质,该活性化合物由此被发育的根吸收。一旦在植物中,其赋予对真菌病原体的抗性。因此,处理生长介质应具有相当的效果。然而,土壤处理并不包括在本发明方法或用途之内,因为其使农民暴露于杀真菌剂I。
通过在种子播种之前将处理施用于种子使操作简化。以此方式例如可在中心场所处理种子,然后将种子分配用于种植。这允许种植种子的人避免处理和使用式I的芳基甲酸联苯基酰胺,并且仅以常用于未处理种子的常规方式处理和种植处理的种子,这减少了对人的暴露。
在本发明的各实施方案中,优选将式(I)的芳基甲酸联苯基酰胺以有效量,即对由种子生长的植物足以提供对抗植物病原性真菌的保护的量施用于种子。当然,本发明方法不仅保护植物,而且保护处理的种子免受真菌侵袭。式(I)的芳基甲酸联苯基酰胺不仅对种子真菌,而且对土壤带有的和叶面的植物病原性真菌有效。
与未处理种子或由未处理种子生长的植物相比,如果对种子和/或植物的损害百分数在真菌侵染10天后(侵染后天数(DAI))对于处理的种子和由处理的种子生长的植物显著降低,则实现了如本文所用的“保护”。为了有效保护,式I的芳基甲酸联苯基酰胺的用量通常为1-500g/100kg种子,优选10-200g/100kg种子。
根据本发明,所述种子处理的一个目的是防治植物病原性真菌。因此,该种子处理涉及杀真菌作用或杀真菌活性,并对由种子生长的植物提供防止真菌造成损害的保护。当然,种子处理也对种子提供防止由真菌造成损害的保护。
如本文所用的术语“杀真菌作用”和“杀真菌活性”是指对目标病原体(其可为任何真菌,但根据本发明包括对豆科植物及其种子的锈病侵染)任何直接和间接作用,分别与未处理种子或由未处理种子生长的植物相比,其导致对处理种子的损害的减少,并且还令人惊讶地导致对果实、根、茎干和/或叶,尤其是对植物的地上部分如果实、茎干,尤其是叶,由处理种子生长的植物的损害的减少。术语“对(第一或第二)病原体的活性”也具有相同含义。该直接或间接作用包括杀死真菌病原体、抑制真菌病原体对植物种子、果实、根、茎干和/或叶的侵染以及抑制或防止真菌病原体的复制。
本发明方法和用途用于保护萌发后,即具有子叶或茎干的下胚轴从种子包衣中破出之后的植物。优选本发明方法和用途用于保护出苗后,即胚芽鞘或子叶或茎干或叶破出土壤表面之后的植物。甚至更优选的是,本发明方法和用途用于保护处于生长阶段09(根据BBCH扩充版;GermanFederal Biological Research Centre for Agriculture and Forestry(德国联邦农业和林业生物研究中性);参见www.bba.de/veroeff/bbch/bbcheng.pdf)或之后的生长阶段的植物。优选保护在其出苗之后且在开花之前(主生长阶段(principal growth stage)0-5),更优选在出苗之后且在出现花之前(主生长阶段0-4),甚至更优选在出苗之后且在可收获的植物生长部分或生长繁殖器官/系统(booting)发育之前(主生长阶段0-3)的植物。在待保护植物为豆科植物,尤其是大豆的情况下,优选当其处于生长阶段09-49,更优选处于生长阶段09-39,甚至更优选处于生长阶段09-29时,应受到保护。在植物为禾谷类,尤其是小麦的情况下,优选处于生长阶段09-59,更优选处于生长阶段09-49,甚至更优选处于生长阶段09-39时,应受到保护。两位数字生长阶段是指BBCH扩充版,而一位数字生长阶段为主生长阶段。
本发明的目标生物体是叶面植物病原性真菌,即侵袭植物的地面上部分,尤其是叶的真菌。然而,本发明用途或方法也提供防止土壤带有的或种子病原体的保护。
本发明的目标生物体优选为豆科植物,尤其是大豆中的真菌病害。最重要的真菌病原体为:
·白粉病菌(Microsphaera diffusa)
·菊池尾孢(Cercospora kikuchii)
·大豆尾孢(Cercospora sojina)
·大豆褐纹病菌(Septoria glycines)
·毛豆炭疽病菌(Colletotrichum truncatum)
·豆薯层锈菌或山马蝗层锈菌
豆薯层锈菌或山马蝗层锈菌代表本发明的特定的目标病原体。
在替代的优选实施方案中,本发明的目标生物体为禾谷类中的真菌病害。在合适的意义上,禾谷类为禾草(pocaceae)的种植形式且例如包括小麦(包括斯佩耳特小麦(spelt)、单粒小麦、二粒小麦、卡姆小麦(kamut)、硬粒小麦和黑小麦)、黑麦、大麦、稻、野生稻、玉米、小米、高粱、埃塞俄比亚画眉草(teff)和燕麦。然而,在本发明中,术语“禾谷类”也包括拟禾谷类(pseudocereal)。它们为阔叶植物(非禾草类)并可以与真实禾谷类相同的方式使用。例如,它们的种子可研磨成粉或者如禾谷类使用。拟禾谷类的实例为苋菜红、奎藜籽和荞麦。最重要的禾谷类真菌病原体为:
·链格孢(Alternaria)属
·小麦裾叶炫菌(Ascochyta tritici),
·禾白粉菌(Blumeria graminis),
·灰葡萄孢(Botrytis cinerea),
·扁豆枝孢(Cladosporium herbarum),
·禾旋孢腔菌(Cochliobolus sativus),
·宫部旋孢腔菌(Cochliobolus miyabeanus),
·玉米小斑病菌(Drechslera maydis),
·大麦网斑内脐蠕孢(Drechslera teres),
·Drechslera tritici-repentis,
·附球菌属(Epicoccum),
·小麦禾白粉菌(Erysiphe graminis),
·大刀镰孢(Fusarium culmorum),
·禾本科镰孢(Fusarium graminearum),
·禾顶囊壳(Gaeumanomyces graminis)属,
·藤仓赤霉(Gibberella fujikuroi),
·Michrodochium nivale,
·禾生球腔菌(Mycosphaerella graminicola),
·小麦基腐病菌(Pseudocercosporella herpotrichoides),
·禾柄锈菌(Puccinia graminis),
·大麦柄锈菌(Puccinia hordei),
·隐匿柄锈菌(Puccinia recondita),
·条形柄锈菌(Puccinia striformins),
·大麦网斑病菌(Pyrenophora teres),
·小麦叶锈菌(Puccinia triticina),
·偃麦草核腔菌(Pyrenophora tritici-repentis),
·Pyricularia grisae,
·禾谷丝核菌(Rhizoctonia cerealis),
·黑麦喙孢(Rhynchosporium secalis),
·小麦颖枯病菌(Septoria nodorum),
·小麦壳针孢(Septoria tritici),
·颖枯壳多孢(Stagonospora nodorum),
·肉孢核瑚菌(Typhula incarnate)。
小麦禾白粉菌、小麦壳针孢和隐匿柄锈菌代表了本发明特定的目标禾谷类病原体。
本发明种子处理可用于防治所述目标害虫和/或保护种子、根和/或田间的地面上部分,叶,种植园,温室,果园或葡萄园作物,观赏植物,种植园或森林树木和/或任何其它令人感兴趣的植物。可用于本发明的种子可为任何植物种类的种子。
然而,种子优选为块茎蔬菜或玉米蔬菜、叶蔬菜、叶菜小棠菜(leafybrassica green)、果实蔬菜、豆科植物或禾谷类的种子。因此,待保护植物优选为块茎蔬菜或玉米蔬菜、叶蔬菜、叶菜小棠菜、果实蔬菜、豆科植物或禾谷类。
优选块茎蔬菜为甜菜根、胡罗卜、木薯、土豆和红萝卜。
优选叶蔬菜为菊苣、苦苣、莴苣、菊苣(radicchio)和菠菜。
优选叶菜小棠菜为花茎甘蓝、抱子甘蓝、卷心菜、花菜和散叶甘蓝。
优选果实蔬菜为黄瓜、茄子、鳄梨、南瓜、西红柿和葫芦。
优选豆类为具有农业用途的那些如菜豆、豌豆、鹰嘴豆、扁豆、大豆和花生,特别优选大豆。
优选禾谷类为合适意义上的禾谷类(=栽培形式的禾草(pocaceae)),如小麦(包括斯佩耳特小麦、单粒小麦、二粒小麦、卡姆小麦、硬粒小麦和黑小麦)、黑麦、大麦、稻、野生稻、玉米、小米、高粱、埃塞俄比亚画眉草和燕麦。以及拟禾谷类如苋菜红、奎藜籽和荞麦。更优选禾谷类为小麦和大麦,特别优选小麦。
在本发明的特别优选的实施方案中,待根据本发明处理的种子为大豆种子。因此,在特别优选的实施方案中,待在萌发后保护的植物为大豆。
大豆可为非转基因植物,如通过常规育种得到的大豆,或可具有至少一个转基因事件。在一个实施方案中,优选大豆植物为具有赋予对农药,优选对除草剂草甘膦具有抗性的转基因事件的转基因植物。因此,优选转基因植物为具有提供草甘膦抗性的转基因事件的植物。这种具有赋予草甘膦抗性的转基因事件的优选转基因植物的一些实例描述于US 5,914,451、US 5,866,775、US 5,804,425、US 5,776,760、US 5,633,435、US 5,627,061、US 5,463,175、US 5,312,910、US 5,310,667、US 5,188,642、US 5,145,783、US 4,971,908和US 4,940,835中。更优选转基因大豆植物具有“毒滴混剂(Roundup-Ready)”转基因大豆(可由Monsanto Company,St.Louis,Mo.得到)的特征。
然而,应理解的是当大豆植物为转基因植物时,存在于植物中的转基因事件并不意味着限制于提供农药抗性的那些,而是可包括任何转基因事件。事实上,在植物中使用“堆积(stacked)”转基因事件也是所预期的。
在本发明的替代的特别优选的实施方案中,待根据本发明处理的种子为小麦种子。因此,在特别优选的实施方案中,待在萌发后保护的植物为小麦。
如本文说所用的成分包括活性成分和助剂。
在本发明中,“活性成分”为直接发挥生物学相关作用,优选上述杀真菌作用的化合物或化合物的组合。
为了拓宽活性谱,活性成分,即式(I)的芳基甲酸联苯基酰胺也可与可用于种子处理的其它活性成分一起使用,例如与杀真菌剂、杀虫剂、杀软体动物剂、杀线虫剂、除草剂、杀藻剂、杀菌剂、灭鼠剂、鸟/哺乳动物驱除剂、生长调节剂、安全剂或者肥料一起使用。
可与式(I)的芳基甲酸联苯基酰胺一起使用的下列活性成分意欲阐述可能的组合,而不施加任何限制:
杀真菌剂:
(1.1)唑类,如糠菌唑(bromoconazole)、环唑醇(cyproconazole)、噁醚唑(difenoconazole)、氧唑菌(epoxiconazole)、喹唑菌酮(fluquinconazole)、氟硅唑(flusilazole)、粉唑醇(flutriafol)、己唑醇(hexaconazole)、烯菌灵(imazalil)、环戊唑菌(metconazole)、腈菌唑(myclobutanil)、戊菌唑(penconazole)、丙环唑(propiconazole)、丙氯灵(prochloraz)、丙硫菌唑(prothioconazole)、戊唑醇(tebuconazole)、氟醚唑(tetraconazole)、三唑酮(triadimefon)、唑菌醇(triadimenol)和戊叉唑菌(triticonazole);
(1.2)酰基丙氨酸类,如苯霜灵(benalaxyl)、甲霜灵(metalaxyl)、mefenoxam、甲呋酰胺(ofurace)和噁霜灵(oxadixyl);
(1.3)胺衍生物如双胍盐(guazatine);
(1.4)苯胺基嘧啶类,如二甲嘧菌胺(pyrimethanil)、嘧菌胺(mepanipyrim)和环丙嘧啶(cyprodinil);
(1.5)二羧酰亚胺类,如异丙定(iprodione)、杀菌利(procymidone)或烯菌酮(vinclozolin);
(1.6)二硫代氨基甲酸盐类,如代森锰锌(mancozeb)、代森联(metiram)和福美双(thiram);
(1.7)杂环化合物如苯菌灵(benomyl)、多菌灵(carbendazim)、萎锈灵(carboxin)、氧化萎锈灵(oxycarboxin)、麦穗宁(fuberidazole)、氟吡菌胺(picobenzamid)、吡噻菌胺(penthiopyrad)、丙氧喹啉(proquinazid)、涕必灵(thiabendazole)和甲基托布津;
(1.8)苯基吡咯类,如拌种咯(fenpiclonil)或氟噁菌(fludioxonil);
(1.9)其它杀真菌剂,如苯噻菌胺(benthiavalicarb)、环氟菌胺(cyflufenamid)、藻菌磷(fosetyl)、乙膦铝(fosetyl-aluminum)、亚磷酸及其盐、异丙菌胺(iprovalicarb)和苯菌酮(metrafenone);
(1.10)嗜球果伞素类,如腈嘧菌酯(azoxystrobin)、醚菌胺(dimoxystrobin)、enestrobin、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)和肟菌酯(trifloxystrobin)、(2-氯-5-[1-(3-甲基苄氧亚氨基)乙基]苄基)氨基甲酸甲酯、(2-氯-5-[1-(6-甲基吡啶-2-基甲氧亚氨基)乙基]苄基)氨基甲酸甲酯和2-邻-[(2,5-二甲基苯氧基亚甲基)苯基]-3-甲氧基丙烯酸甲酯;
(1.11)肉桂酰胺及类似化合物,如烯酰吗啉(dimethomorph)、氟联苯菌(flumetorver)和氟吗啉(flumorph);
杀虫剂/杀螨剂
(2.1)有机(硫代)磷酸酯类,其选自高灭磷(Acephate)、唑啶磷(azamethiphos)、谷硫磷(Azinphos-methyl)、毒死蜱(Chlorpyrifos)、甲基毒死蜱(chlorpyrifos-methyl)、毒虫畏(Chlorfenvinphos)、二嗪农(Diazinon)、敌敌畏(Dichlorvos)、百治磷(Dicrotophos)、乐果(Dimethoate)、乙拌磷(Disulfoton)、乙硫磷(Ethion)、杀螟松(Fenitrothion)、倍硫磷(Fenthion)、异噁唑磷(Isoxathion)、马拉硫磷(Malathion)、甲胺磷(Methamidophos)、杀扑磷(Methidathion)、甲基一六零五(Methyl-Parathion)、速灭磷(Mevinphos)、久效磷(Monocrotophos)、砜吸磷(Oxydemeton-methyl)、对氧磷(Paraoxon)、一六零五(Parathion)、稻丰散(Phenthoate)、伏杀磷(Phosalone)、亚胺硫磷(Phosmet)、磷胺(Phosphamidon)、甲拌磷(Phorate)、辛硫磷(Phoxim)、虫螨磷(Pirimiphos-methyl)、丙溴磷(Profenofos)、丙硫磷(Prothiofos)、乙丙硫磷(Sulprophos)、杀虫畏(tetrachlorvinphos)、特丁磷(terbufos)、三唑磷(Triazophos)和敌百虫(Trichlorfon);
(2.2)氨基甲酸酯类,其选自棉铃威(alanycarb)、涕灭威(aldicarb)、噁虫威(bendiocarb)、丙硫克百威(benfuracarb)、甲萘威(carbaryl)、虫螨威(carbofuran)、丁硫克百威(carbosulfan)、双氧威(fenoxycarb)、呋线威(furathiocarb)、灭虫威(methiocarb)、灭多虫(methomyl)、甲氨叉威(oxamyl)、抗蚜威(pirimicarb)、残杀威(propoxur)、硫双威(thiodicarb)和唑蚜威(triazamate);
(2.3)合成除虫菊酯类,其选自丙烯除虫菊(allethrin)、氟氯菊酯(bifenthrin)、乙氰菊脂(cycloprothrin)、氟氯氰菊酯(cyfluthrin)、RS-氯氟氰菊酯(cyhalothrin)、cyphenothrin、氯氰菊酯(cypermethrin)、甲体氯氰菊酯(alpha-cypermethrin)、乙体氯氰菊酯(beta-cypermethrin)、己体氯氰菊酯(zeta-cypermethrin)、溴氰菊酯(deltamethrin)、高氰戊菊酯(esfenvalerate)、醚菊酯(etofenprox)、甲氰菊酯(fenpropathrin)、杀灭菊酯(fenvalerate)、氟氰戊菊酯(flucythrinate)、咪炔菊酯(imiprothrin)、氯氟氰菊酯(Lambda-Cyhalothrin)、γ-氯氟氰菊酯(gamma-cyhalothrin)、氯菊酯(permethrin)、炔酮菊酯(prallethrin)、除虫菊酯(pyrethin)I和II、灭虫菊(resmethrin)、灭虫硅醚(silafluofen)、氟胺氰菊酯(Tau-Fluvalinate)、七氟菊酯(tefluthrin)、胺菊酯(tetramethrin)、四溴菊酯(tralomethrin)、四氟菊酯(transfluthrin)和丙氟菊酯(profluthrin)、四氟甲醚菊酯(dimefluthrin);
(2.4)选自如下的生长调节剂:a)几丁质合成抑制剂,其选自苯甲酰基脲、双三氟虫脲(bistrifluron)、定虫隆(chlorfluazuron)、cyramazin、氟脲杀(diflubenzuron)、氟螨脲(flucycloxuron)、氟虫脲(flufenoxuron)、氟铃脲(hexaflumuron)、氟丙氧脲(lufenuron)、双苯氟脲(novaluron)、伏虫隆(teflubenzuron)和杀虫隆(triflumuron)、噻嗪酮(buprofezin)、噁茂醚(diofenolan)、噻螨酮(hexythiazox)、特苯噁唑(etoxazole)和四螨嗪(clofentazine);b)蜕皮激素拮抗剂,其选自特丁苯酰肼(halofenozide)、甲氧苯酰肼(methoxyfenozide)、双苯酰肼(tebufenozide)和艾扎丁(Azadirachtin);c)保幼激素类似物,其选自蚊蝇醚(pyriproxyfen)、蒙五一五(methoprene)和双氧威(fenoxycarb);d)类脂生物合成抑制剂,其选自螺螨酯(spirodiclofen)、螺甲螨酯(spiromesifen)和螺虫乙酯(spirotetramat);
(2.5)烟碱受体激动剂/拮抗剂化合物,其选自噻虫胺(Clothianidin)、呋虫胺(dinotefuran)、吡虫啉(Imidacloprid)、噻虫嗪(Thiamethoxam)、硝胺烯啶(Nitenpyram)、吡虫清(acetamiprid)、噻虫啉(Thiacloprid);
(2.6)GABA拮抗剂化合物,其选自氯丹acetoprole、硫丹(endosulfan)、乙虫清(ethiprole)、锐劲特(fipronil)、氟吡唑虫(vaniliprole);
(2.7)大环内酯杀虫剂,其选自齐墩螨素(abamectin)、甲氨基阿维菌素(emamectin)、米尔螨素(milbemectin)、lepimectin、艾克敌105(spinosad);
(2.8)METI I化合物,其选自喹螨醚(fenazaquin)、哒螨酮(pyridaben)、吡螨胺(tebufenpyrad)、唑虫酰胺(tolfenpyrad)和flufenerim;
(2.9)METI II和III化合物,其选自灭螨醌(acequinocyl)、fluacyprim和灭蚁腙(hydramethylnon);
(2.10)分离剂化合物:氟唑虫清(chlorfenapyr);
(2.11)氧化磷酸化抑制剂化合物,其选自三环锡(cyhexatin)、杀螨硫隆(diafenthiuron)、杀螨锡(fenbutatin oxide)和克螨特(propargite);
(2.12)蜕皮干扰剂(Moulting disruptor)化合物:cryomazine;
(2.13)混合功能氧化酶抑制剂化合物:增效醚(piperonyl butoxide);
(2.14)钠通道阻断剂化合物,其选自氰氟虫胺(metaflumizone)和噁二唑虫(indoxacarb);
(2.15)选自下列的化合物:benclothiaz、联苯肼酯(bifenazate)、杀螟丹(cartap)、氟啶虫酰胺(flonicamid)、啶虫丙醚(pyridalyl)、拒嗪酮(pymetrozine)、硫、硫环杀(thiocyclam)、氟虫酰胺(flubendiamide)、cyenopyrafen、吡氟硫磷(flupyrazofos)、丁氟螨酯(cyflumetofen)、amidoflumet、式Γ1的氨基异噻唑化合物:
其中Ri为-CH2OCH2CH3或H且Rii为CF2CF2CF3或CH2CH(CH3)3,
式Γ2的邻氨基苯甲酰胺(anthranilamide)化合物:
其中B1为氢、CN或Cl,B2为Br或CF3且RB为氢、CH3或CH(CH3)2;
以及描述于JP 2002-284608、WO 02/89579、WO 02/90320、WO02/90321、WO 04/06677、WO 04/20399或JP 2004-99597中的丙二腈化合物。
·杀软体动物剂;
·杀线虫剂;
·除草剂,例如咪唑啉酮除草剂如咪草烟(imazethapyr)、咪草啶酸(imazamox)、灭草烟(imazapyr)和甲基咪草烟(imazapic)或精噻吩草胺(dimethenamid-P);
·杀藻剂;
·杀菌剂;
·生物制剂;
·鸟/哺乳动物驱除剂;
·肥料;
·熏蒸剂;
·生长调节剂;
·灭鼠剂。
杀软体动物剂、杀线虫剂、除草剂、杀藻剂、杀菌剂、生物制剂、鸟/哺乳动物驱除剂、肥料、熏蒸剂、生长调节剂和灭鼠剂对本领域技术人员是众所周知的。
根据特定的实施方案,将式(I)的芳基甲酸联苯基酰胺与唑类杀真菌剂,尤其是氧唑菌(epoxyconazole)、喹唑菌酮、粉唑醇、环戊唑醇、丙硫菌唑或戊叉唑菌组合使用。
根据另一特定的实施方案,将式(I)的芳基甲酸联苯基酰胺与至少一种杀虫剂组合使用。至少一种杀虫剂优选选自吡虫清、甲体氯氰菊酯、乙体氯氰菊酯、氟氯菊酯、虫螨威、丁硫克百威、噻虫胺、乙氰菊酯、氟氯氰菊酯、氯氰菊酯、溴氰菊酯、氟脲杀、呋虫胺、醚菊酯、杀螨锡、甲氰菊酯、锐劲特、氟氰戊菊酯、吡虫啉、γ-氯氟氰菊酯、硝胺烯啶、信息激素(pheromones)、艾克敌105、伏虫隆、七氟菊酯、特丁磷、噻虫啉、噻虫嗪、硫双威、四溴菊酯、唑蚜威、己体氯氰菊酯、螺虫乙酯、吡氟硫磷、唑虫酰胺、氟虫酰胺、双三氟虫脲、benclothiaz、pyrafluprole、pyriprole、amidoflumet、flufenerim、丁氟螨酯、cyenopyrafen、Γ2的邻氨基苯甲酰胺化合物,其中B1为Cl,B2为Br且RB为CH3;以及Γ2的邻氨基苯甲酰胺化合物,其中B1为CN、B2为Br且RB为CH3。
优选杀虫剂为GABA拮抗剂化合物,此处优选锐劲特,和烟碱受体激动剂和/拮抗剂化合物,此处优选噻虫胺、吡虫啉和噻虫嗪。特别优选的杀虫剂为锐劲特。
如果式(I)的芳基甲酸联苯基酰胺与其它活性成分,特别是与唑类杀真菌剂和/或锐劲特联合使用,则式(I)的芳基甲酸联苯基酰胺与其它活性成分用量的重量比通常为1:100-100:1,优选1:50-50:1,尤其是1:10-10:1。
如果将式(I)的芳基甲酸联苯基酰胺与另一种活性成分联合使用,则该活性成分可与式(I)的芳基甲酸联苯基酰胺同时使用或在短的时间间隔之后使用,例如在用式(I)的芳基甲酸联苯基酰胺处理之前或之后数天内使用。在同时施用的情况下,种子处理可以单途径进行,其中施用包含式(I)的芳基甲酸联苯基酰胺和另一活性成分的组合物,或者以分开的途径进行,其中施用各活性成分的不同配制剂。
活性成分在即用制剂中的浓度可在显著范围内变化。它们基于制剂总重量通常为0.01-80重量%,常常0.1-50重量%,优选0.5-20重量%。活性成分也可成功地以浓缩形式施用,其中可以向种子施加超过80重量%活性成分的制剂,或甚至不含添加剂的活性成分。添加剂的量在每种情况下基于制剂总重量通常不超过30重量%,优选20重量%,尤其为0.1-20重量%。
原则上,可使用所有常规处理种子的方法,尤其是拌种如种子包衣(如造粒)和种子吸取(如浸泡)。具体而言,种子处理按照其中使种子暴露于特定所需量的包含式I芳基甲酸联苯基酰胺的制剂的程序。制剂可为直接或在预先例如用水稀释之后施用的配制剂,有利的是可将种子处理配制剂稀释2-10倍,从而产生0.01-60重量%,优选0.1-40重量%活性化合物的即用组合物浓度。
通常使用适合于此的装置,例如用于固体或固体/液体组分的混合器,直至制剂均匀分布在种子上。因此,制剂可通过标准种子处理方法施加至种子,其包括但不限于在容器(如瓶、袋或转鼓)混合,机械施加,转鼓处理,喷雾和浸渍。合适的话,随后干燥。
本发明的特定实施方案包括种子包衣和吸取(如浸泡)。“包衣”是指赋予种子外表面部分或完整的非植物材料层的任何方法,“吸取”是指导致活性成分穿透入种子的可萌发部分和/或其天然外壳(sheath)、(内)壳(husk)、皮(hull)、壳、荚和/或珠被(integument)的任何方法。因此,本发明还涉及其包括向种子提供包含式(I)的芳基甲酸联苯基酰胺的包衣的种子处理,以及包括使种子吸取式(I)的芳基甲酸联苯基酰胺的种子处理。
在容许高负载的式(I)的芳基甲酸联苯基酰胺中,包衣特别有效,所述高负载在处理典型的难以防治的真菌病原体时需要,同时防止由于式(I)的芳基甲酸联苯基酰胺的负载增加而引起的不可接受的植物毒性。
包衣可使用常规包衣技术和机器如流化床技术、辊研磨机方法、滚动静态(rotostatic)种子处理器和转鼓涂敷机而施用于种子。其它方法如喷淋床技术也可能是有用的。种子可在包衣之前预施胶。在包衣之后,通常将种子干燥,然后转移至施胶机中施胶。
这类程序在本领域是已知的。种子包衣方法和应用它们的装置例如公开于US 5,918,413、US 5,891,246、US 5,554,445、US 5,389,399、US5,107,787、US 5,080,925、US 4,759,945和US 4,465,017中。
在另一特定实施方案中,固体的式(I)的芳基甲酸联苯基酰胺,例如作为固体细颗粒配制剂,如粉末或粉剂可直接与种子混合。可任选使用增粘剂以将固体,如粉末粘附至种子表面。例如,可将一定量的种子与增粘剂(其增加颗粒在种子表面上的粘附)混合并任选搅动以促进增粘剂对种子的均匀涂敷。例如,种子可与足够量的增粘剂混合,这导致增粘剂对种子的部分或完全涂敷。然后将如此预处理的种子与含有式(I)的芳基甲酸联苯基酰胺的固体配制剂混合,以实现固体配制剂在种子材料表面上的粘附。该混合物例如可通过转鼓搅动,以促进增粘剂与固体芳基甲酸联苯基酰胺的接触,由此导致固体芳基甲酸联苯基酰胺I粘附在种子上。
用式(I)的芳基甲酸联苯基酰胺处理种子的另一特定方法为吸取。例如,可使种子与在溶剂如水中包含约1-约75重量%式(I)的芳基甲酸联苯基酰胺的水溶液结合一段时间。
优选,溶液的浓度为约5-约50重量%,更优选约10-约25重量%。
在种子与溶液结合的过程中,种子吸收(吸取)至少部分式(I)的芳基甲酸联苯基酰胺。任选地,可例如通过振摇、滚动、转鼓或其它手段搅动种子和溶液的混合物。在吸取方法之后,可将种子与溶液分离,并任选以合适的方式,如通过轻拍或风干而干燥。
在本发明的又一特定的实施方案中,式(I)的芳基甲酸联苯基酰胺可通过使用固体基质打底(priming)而引至种子上或种子内。例如,可将一定量的式(I)的芳基甲酸联苯基酰胺与固体基质材料混合,然后可放入种子,使其与固体基质材料接触一段时间,以允许将式(I)的芳基甲酸联苯基酰胺引至种子。然后可任选将种子的混合物与固体基质材料分离并储存或使用,或可优选将固体基质材料加上种子直接储存或种植/播种。
如上所述,式(I)的芳基甲酸联苯基酰胺和任选的其它活性成分可直接使用,即不存在任何助剂。然而,式(I)的芳基甲酸联苯基酰胺和其它活性成分通常以组合物的形式施用于种子。
如用于本文的“组合物”包含至少一种活性成分和至少一种助剂。
术语“助剂”是指其本身不具有生物相关作用,但支持活性成分作用的化合物或化合物组合。当使用助剂时,它们的选择取决于活性成分和所选择的用于种子处理的程序。
通常而言,组合物因此包含活性成分组分(“A”)和助剂组分(“B”)。组合物的活性成分组分(“A”)包含式I的芳基甲酸联苯基酰胺(“A1”)和任选的一种或多种其它活性成分(“A2”)。助剂组分(“B”)包含一种或多种助剂。
通常而言,组合物包含0.005-95重量%,优选0.1-90重量%,尤其是5-50重量%活性组分“A”,其中由组分“B”形成平衡。在本文中,活性成分以90-100%,优选95-100%的纯度使用(根据NMR谱)。根据特定的实施方案,组分“A”基本由式I的芳基甲酸联苯基酰胺组成,即组合物的活性成分为式I的芳基甲酸联苯基酰胺。
在本发明的特定的实施方案中,组合物可额外包含一种或多种用于温血动物如鸟、狗和刺猬的驱除剂,如壬酸香草基酰胺。驱除剂的量基于组合物的总重量优选为0.1-5重量%。
根据特定的实施方案,组合物为种子处理配制剂。本发明种子处理配制剂包含至少一种特别适合种子处理的助剂,即尤其促进式I的芳基甲酸联苯基酰胺与种子的粘合和/或渗透入种子中和/或另外改进组合物或用组合物处理的种子的稳定性和/或易处理性的助剂。因此,本发明还涉及一种种子处理配制剂,其包含式I的芳基甲酸联苯基酰胺、至少一种种子处理助剂和任选的一种或多种其它助剂。
种子处理助剂尤其选自适合种子包衣材料的试剂、适合固体基质打底材料的试剂、适合促进种子吸取的渗透改进剂、着色剂、防冻剂和胶凝剂。
根据优选实施方案,种子包衣材料包含粘合剂(或增粘剂)。包衣材料还任选包含一种或多种选自填料和增塑剂的额外的种子处理助剂。
粘合剂(或增粘剂)为可用于种子处理配制剂的所有常规粘合剂(或增粘剂)。可用于本发明的粘合剂(或增粘剂)优选包含可以是天然或部分或全部合成的且对待包衣的种子没有植物毒性作用的粘合聚合物。优选粘合剂(或增粘剂)可生物降解。优选选择起式I的芳基甲酸联苯基酰胺的基质作用的粘合剂或增粘剂。
粘合剂(或增粘剂)可选自聚酯、聚醚酯、聚酸酐、聚酯型聚氨酯、聚酯酰胺;聚乙酸乙烯酯;聚乙酸乙烯酯共聚物;聚乙烯醇和纤基乙酸钠;聚乙烯醇共聚物;聚乙烯基吡咯烷酮;多糖,包括淀粉、改性淀粉和淀粉衍生物,糊精,麦芽糊精,藻酸盐,壳聚糖和纤维素,纤维素酯,纤维素醚和纤维素醚酯,包括乙基纤维素、甲基纤维素、羟甲基纤维素、羟丙基纤维素和羧甲基纤维素;脂;油;蛋白质,包括酪蛋白、明胶和玉米蛋白;阿拉伯胶;紫胶;偏二氯乙烯和偏二氯乙烯共聚物;木素磺酸盐,尤其是木素磺酸钙;聚丙烯酸酯、聚甲基丙烯酸酯和丙烯酸类共聚物;聚乙烯基丙烯酸酯;聚氧乙烯;聚丁烯、聚异丁烯、聚苯乙烯、聚乙烯胺、聚乙烯酰胺;丙烯酰胺聚合物和共聚物;聚丙烯酸羟乙酯、甲基丙烯酰胺单体;和聚氯丁二烯。在特定的实施方案中,粘合剂为热塑性聚合物。
在本发明的特定的实施方案中,种子处理配制剂含有至少一种聚酯,其尤其选自聚交酯、部分芳族聚酯(对苯二甲酸、己二酸和脂族二醇的共聚物)、聚乙醇酸交酯、聚羟基链烷酸酯和聚酒石酸酯(polytartrate)。
粘合剂(或增粘剂)在配制剂中的量可变化,但为总重量的约0.01-约25%,更优选约1-约15%,甚至更优选约5-约10%。
如上所述,包衣材料也可任选包含填料。填料可为吸收剂或惰性填料,如本领域已知的那些且可包括木细粉,谷粉,树皮粉,木粉和坚果壳粉,糖类,尤其是多糖,活性炭,细颗粒无机固体,硅胶,硅酸盐,粘土,白垩,硅藻土,碳酸钙,碳酸镁,白云石,氧化镁,硫酸钙等。可使用的粘土和无机固体包括钙膨润土、高岭土、陶土、滑石、珍珠岩、云母、蛭石、硅酸盐、石英粉、蒙脱土、绿坡缕石、红玄武土、黄土、石灰石、石灰及其混合物。可使用的糖类包括糊精和麦芽糊精。谷粉包括小麦粉、燕麦粉和大麦粉。填料也可包含肥料物质如硫酸铵、磷酸铵、硝酸铵、尿类及其混合物。
选择填料以使其对种子提供合适的小气候,例如使用填料以增加活性成分的负载率和调节活性成分的控制-释放。填料可有助于种子的生产或包衣加工。填料量可变化,但填料组分的重量通常为总重量的约0.05-约75%,更优选约0.1-约50%,甚至更优选约0.5-15%。
优选选择粘合剂(或增粘剂)以使其可用作式I的芳基甲酸联苯基酰胺的基质。虽然如上所公开的粘合剂均可用作基质,优选形成一种或多种粘合剂化合物的固体连续相,其中分布式I的芳基甲酸联苯基酰胺的非连续相。任选填料和/或其它组分也可存在于基质中。术语“基质”应理解为包括视为基质体系、储存体系或微胶囊体系的那些。通常而言,基质体系由均匀分散在聚合物中的式I的芳基甲酸联苯基酰胺和填料组成,而储存体系由包含式(I)的芳基甲酸联苯基酰胺或其盐的分散相组成,式(I)的芳基甲酸联苯基酰胺或其盐物理分散在周围的限制速率的聚合物相。微胶囊化包括小颗粒或液滴包衣,以及固体基质中的分散体。
尤其是如果用于包衣的式I的芳基甲酸联苯基酰胺为油性类型的组合物并且存在少量或不存在惰性填料,则可能有用的是通过干燥组合物加速干燥过程。该任选步骤可伴随本领域众所周知的措施且可包括加入碳酸钙、高岭土或膨润土粘土、珍珠岩、硅藻土,或任何吸收材料,其优选与式I的芳基甲酸联苯基酰胺的包衣层一起加入以吸收油或过量水分。有效提供干燥包衣所需吸收剂量为种子重量的约0.5-约10%。
任选包衣材料包含增塑剂。增塑剂常用于使包衣层形成的膜更柔软,以改进粘合和伸展性,以及改进加工速率。改进的膜的柔软性对储存、处理和播种过程中的碎片、碎裂或剥落最小化具有重要性。可使用许多种增塑剂,然而,有用的增塑剂包括聚乙二醇、低聚亚烷基二醇、甘油、烷基苄基邻苯二甲酸酯,尤其是丁基苄基邻苯二甲酸酯,二醇苯甲酸酯和相关的化合物。
增塑剂在包衣层中的量为约0.1-约20重量%。
适用于可用于本发明的固体基质打底材料的试剂包括聚丙烯酰胺、淀粉、粘土、硅石、氧化铝、土壤、沙、聚脲、聚丙烯酸酯,或能够吸收或吸附式I的芳基甲酸联苯基酰胺一段时间并能够将式I的芳基甲酸联苯基酰胺释放入种子中或种子上的任何其它材料。其用于确保式I的芳基甲酸联苯基酰胺和固体基质材料相互相容。例如,应选择固体基质材料,以使其可以合理的速率,例如经数分钟、数小时或数天释放式I的芳基甲酸联苯基酰胺。
适合促进种子吸取的渗透改进剂包括可农用表面活性化合物。渗透改进剂的量基于配制剂总重量通常不超过20重量%。优选渗透改进剂的量为2-20重量%。
本发明着色剂为常用于此的所有染料和颜料。就此而言,可以使用微溶于水的颜料和可溶于水的染料。例如作为实例可以提到如下已知的着色剂:若丹明B、C.I.颜料红112和C.I.溶剂红1、颜料蓝15:4、颜料蓝15:3、颜料蓝15:2、颜料蓝15:1、颜料蓝80、颜料黄1、颜料黄13、颜料红48:2、颜料红48:1、颜料红57:1、颜料红53:1、颜料橙43、颜料橙34、颜料橙5、颜料绿36、颜料绿7、颜料白6、颜料棕25、碱性紫10、碱性紫49、酸性红51、酸性红52、酸性红14、酸性蓝9、酸性黄23、碱性红10、碱性红108。着色剂量通常不超过配制剂的20重量%,优选基于配制剂总重量为1-15重量%。通常优选着色剂也用作温血动物的驱除剂,如氧化铁、二氧化钛、普鲁士蓝、蒽醌染料、偶氮染料和金属酞菁染料。
可特别用于含水配制剂的防冻剂原则上为所有导致水的熔点降低的那些物质。合适的防冻剂包括醇类如甲醇、乙醇、异丙醇、丁醇、乙二醇、甘油、二乙基乙二醇等。防冻剂的量基于配制剂总重量不超过20重量%,经常为1-15重量%。
合适的胶凝剂为可为此用于农业化学组合物中的所有物质,例如纤维素衍生物、聚丙烯酸衍生物,黄原胶,改性粘土,尤其是有机改性的层状硅酸盐和高度分散的硅酸盐。特别合适的胶凝剂为角叉菜胶()。胶凝剂的量基于配制剂的总重量不超过配制剂的5重量%,优选为0.5-5重量%。
可存在于种子处理配制剂中的其它助剂包括溶剂、润湿剂、分散剂、乳化剂、表面活性剂、稳定剂、保护胶体、消泡剂和防腐剂。
合适的溶剂的实例为水或有机溶剂如芳族溶剂(如产品、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(N-甲基吡咯烷酮、N-辛基吡咯烷酮)、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。然而,根据特定的实施方案,本发明配制剂含有小于10重量%,优选小于6重量%的所述有机溶剂。
合适的表面活性化合物为所有适合配制农业活性成分,尤其是式I的芳基甲酸联苯基酰胺的那些表面活性剂,其可以是非离子、阳离子、阴离子或两性的。根据它们的作用,表面活性剂-有时称作“添加剂”-可分为润湿剂、分散剂、乳化剂或保护胶体;然而,这些特定的组可重叠并且不可严格划分。表面活性剂的量基于配制剂的总重量通常不超过20重量%,经常为1-15重量%。
合适的润湿剂为所有促进润湿且常用于配制农业活性成分的那些物质。可优选使用烷基萘磺酸盐如二异丙基-或二异丁基萘磺酸盐。
合适的分散剂和/或乳化剂为所有常用于配制农业活性成分的非离子、阴离子和阳离子分散剂或乳化剂。可优选使用以下那些:非离子或阴离子分散剂和/或乳化剂,或非离子或阴离子分散剂和/或乳化剂的混合物。
可使用的合适的非离子分散剂和/或乳化剂尤其为氧化乙烯/氧化丙烯嵌段共聚物、烷基酚聚乙二醇醚和三苯乙烯基酚聚乙二醇醚,例如聚氧乙烯辛基酚醚,乙氧基化异辛基酚、辛基酚、壬基酚,烷基酚聚乙二醇醚,三丁基苯基聚乙二醇醚,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,山梨醇酯和甲基纤维素。然而,根据特定的实施方案,本发明配制剂含有低于10重量%,优选低于6重量%氧化乙烯/氧化丙烯嵌段共聚物,更特别是低于10重量%,优选低于6重量%所述非离子分散剂和/或乳化剂。
可使用的合适的分散剂和/或乳化剂尤其为木素磺酸、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,还有芳基磺酸盐/甲醛缩合物,如磺化萘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,木素磺酸盐,木素亚硫酸盐废液,磷酸化或硫酸化甲基纤维素衍生物和聚丙烯酸的盐。
保护胶体通常为水溶性的两性聚合物。实例包括蛋白质和变性蛋白如酪蛋白,多糖如水溶性淀粉衍生物和纤维素衍生物,尤其是疏水改性淀粉和纤维素,还有聚羧酸化物如聚丙烯酸和丙烯酸共聚物,聚乙烯醇,聚乙烯基吡咯烷酮,乙烯基吡咯烷酮共聚物,聚乙烯胺,聚乙烯亚胺和聚亚烷基醚。
可使用的消泡剂为所有抑制泡沫形成且常用于配制农业化学活性成分的那些物质。特别合适的是聚硅氧烷消泡剂,即聚硅氧烷含水乳液(例如Wacker的 SRE,或Rhodia的),长链醇类,脂肪酸及其盐,如硬脂酸镁。消泡剂的量基于配制剂的总重量通常不超过配制剂的3重量%,优选为0.1-2重量%。
可使用的防腐剂为所有为此用于农业化学组合物的防腐剂。可提及的实例为二氯芬、异噻唑啉酮(isothiazolene)和异噻唑酮(isothiazolone)类,如1,2-苯并异噻唑-3(2H)-酮、2-甲基-2H-异噻唑-3-酮-盐酸盐、5-氯-2-(4-氯苄基)-3(2H)-异噻唑酮、5-氯-2-甲基-2H-异噻唑-3-酮、5-氯-2-甲基-2H-异噻唑-3-酮、5-氯-2-甲基-2H-异噻唑-3-酮-盐酸盐、4,5-二氯-2-环己基-4-异噻唑啉-3-酮、4,5-二氯-2-辛基-2H-异噻唑-3-酮、2-甲基-2H-异噻唑-3-酮、2-甲基-2H-异噻唑-3-酮-氯化钙配合物、2-辛基-2H-异噻唑-3-酮和苄醇半缩醛。防腐剂的量基于配制剂的总重量通常不超过配制剂的2重量%,优选为0.01-1重量%。
熟练技术人员熟知活性成分的农业组合物。其实例包括水溶性浓缩物(SL、LS)、分散性浓缩物(DC)、乳油(EC)、乳液(EW、EO、ES)、悬浮液(SC、OD、FS)、水分散性颗粒(WG、SG)、水分散性或水溶性粉末(WP、SP、SS、WS)、粉剂或可撒粉粉末(DP、DS)、颗粒(GR、FG、GG、MG)、ULV溶液(UL)和凝胶配制剂(GF)。熟练技术人员例如由Ullmann’sEncyclopedia of Industrial Chemistry,Fungicides,第4章,第5版,CD-ROM,Wiley-VCH,1997和Mollet,H.,Grubemann,A.,Formulationtechnology,Wiley VCH Verlag GmbH,Weinheim(德意志联邦共和国),2001熟知这类组合物。对种子处理而言,这类组合物可直接施用或在加入合适的液体,尤其是水以溶解、乳化、分散、悬浮或稀释组合物之后施用。因此,施用于种子的即用制剂的类型取决于所用组合物的类型和用于处理种子的方法。
这类组合物可以以已知方式制备(例如参见综述US 3,060,084,EP-A707 445(对于液体浓缩物),Browning,“Agglomeration”(团聚),ChemicalEngineering,1967年,12月4日,147-48,Perry’s Chemical Engineer’sHandbook,第4版,McGraw-Hill,New York,1963,第8-57页及随后各页。WO 91/13546,US 4,172,714,US 4,144,050,US 3,920,442,US5,180,587,US 5,232,701,US 5,208,030,GB 2,095,558,US 3,299,566,Klingman,Weed Control as a Science(杂草防治科学),John Wiley andSons,Inc.,New York,1961,Hance等,Weed Control Handbook(杂草防治手册),第8版,Blackwell Scientific Publications,Oxford,1989和Mollet,H.,Grubemann,A.,Formulation technology(配制技术),WileyVCH Verlag GmbH,Weinheim(德国),2001,2.D.A.Knowles,Chemistryand Technology of Agrochemical Formulations(农业配制剂化合物和技术),Kluwer Academic Publishers,Dordrecht,1998(ISBN 0-7514-0443-8)),例如通过将活性组分与一种或多种助剂粘附而制备。
如下实施例简单阐述所述组合物:
A)水溶性浓缩物、溶液(SL、LS)
将10重量份芳基甲酸联苯基酰胺I溶于90重量份水或水溶性溶剂中。或者,向式(I)的苯基缩氨脲或其可农用盐中加入湿润剂或其它助剂。式(I)的苯基缩氨脲或其可农用盐经水稀释溶解。以此方式得到芳基甲酸联苯基酰胺I含量为10重量%的配制剂。
B)分散性浓缩物(DC)
将20重量份芳基甲酸联苯基酰胺I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。由此得到具有20重量%芳基甲酸联苯基酰胺I的配制剂。
C)乳油(EC)
将15重量份芳基甲酸联苯基酰胺I溶于7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。由此得到具有15重量%芳基甲酸联苯基酰胺I的配制剂。
D)乳液(EW、EO、ES)
将25重量份芳基甲酸联苯基酰胺I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。由此得到具有25重量%芳基甲酸联苯基酰胺I的配制剂。E)悬浮液(SC、OD、FS)
在搅拌的球磨机中,将20重量份芳基甲酸联苯基酰胺I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芳基甲酸联苯基酰胺I悬浮液。由此得到具有20重量%芳基甲酸联苯基酰胺I的配制剂。
F)水分散性颗粒(WG、SG)
将50重量份芳基甲酸联苯基酰胺I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。由此得到具有50重量%芳基甲酸联苯基酰胺I的配制剂。
G)水分散性粉末和水溶性粉末(WP、SP、SS、WS)
将75重量份芳基甲酸联苯基酰胺I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。由此得到具有75重量%芳基甲酸联苯基酰胺I的配制剂。
H)粉剂和可撒粉粉末(DP、DS)
将5重量份芳基甲酸联苯基酰胺I细碎研磨并与95重量份细碎高岭土充分混合。这得到芳基甲酸联苯基酰胺I含量为5重量%的可撒粉产品。
J)颗粒(GR、FG、GG、MG)
将0.5重量份芳基甲酸联苯基酰胺I细碎研磨并结合99.5重量份载体。由此得到具有0.5重量%芳基甲酸联苯基酰胺I的配制剂。现行方法是挤出、喷雾干燥或流化床方法。这得到不经稀释而叶面施用的颗粒。
K)ULV溶液(UL)
将10重量份芳基甲酸联苯基酰胺I溶于90重量份有机溶剂如二甲苯中。这得到不经稀释而叶面施用的芳基甲酸联苯基酰胺I含量为10重量%的产品。
L)凝胶配制剂(GF)
在搅拌的球磨机中,将20重量份芳基甲酸联苯基酰胺I粉碎并加入10重量份分散剂、1重量份胶凝剂湿润剂以及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芳基甲酸联苯基酰胺I悬浮液,由此得到具有20重量%芳基甲酸联苯基酰胺I的配制剂。
对于根据本发明的种子处理,优选粉末,如水分散性、水溶性和可撒粉粉末,粉剂和悬浮液。此外,优选凝胶配制剂。还可有利地使用水溶性浓缩物和乳液。
根据本发明特别优选如下配制剂:可流动浓缩物(特别是FS);溶液(特别是LS);用于干处理的粉末(特别是DS);用于淤浆处理的水分散性粉末(特别是WS);水溶性粉末(特别是SS)和乳液(特别是ES)。还优选凝胶配制剂(特别是GF)。这些配制剂可经稀释或不经稀释而施用于种子。
根据特定的实施方案,将FS配制剂用于种子处理。通常而言,FS配制剂可包含1-800g/l芳基甲酸联苯基酰胺I,1-200g/l表面活性剂,0-200g/l防冻剂,0-400g/l粘合剂,0-200g/l着色剂和至多1升溶剂,优选水。
根据另一特定实施方案,本发明种子处理配制剂为种子包衣配制剂。
这类种子包衣配制剂包含芳基甲酸联苯基酰胺I、至少一种粘合剂(或增粘剂)和任选至少一种选自填料和增塑剂的其它助剂。
包含粘合剂、填料和/或增塑剂的种子包衣配制剂在本领域是众所周知的。种子包衣配制剂例如公开于US 5,939,356、US 5,882,713、US 5,876,739、US 5,849,320、US 5,834,447、US 5,791,084、US 5,661,103、US 5,622,003、US 5,580,544、US 5,328,942、US 5,300,127、US 4,735,015、US 4,634,587、US 4,383,391、US 4,372,080、US 4,339,456、US 4,272,417和US 4,245,432和其它文献中。
包括在包衣配制剂中的式I的芳基甲酸联苯基酰胺的量取决于种子类型而变化,但包衣配制剂应含有杀真菌有效量的芳基甲酸联苯基酰胺I。芳基甲酸联苯基酰胺I在包衣配制剂中的量通常为总重量的约0.005-约75%。芳基甲酸联苯基酰胺I的更优选的范围是约0.01-约40%;更优选约0.05-约20%。
包括在包衣配制剂中的芳基甲酸联苯基酰胺I确切量由本领域熟练技术人员容易地确定且取决于待包衣的种子的尺寸和其它特征(表面结构等)而变化。包衣配制剂的芳基甲酸联苯基酰胺I不准抑制种植萌发且应在目标病原体对种子或植物造成损害的其生命周期中有效保护种子和/或植物。包衣通常应在播种后有效约0-120天,优选约0-60天。
由芳基甲酸联苯基酰胺I形成的包衣配制剂能够通过扩散或运动经由基质以缓慢速率释放芳基甲酸联苯基酰胺I至种子或周围介质中。
本发明还提供了通过上述本发明方法处理的种子。还提供了可通过上述方法得到的种子。
此外,本发明还提供了用上述种子处理配制剂处理的种子,尤其是用配制剂涂覆的种子或含有该配制剂的种子。还提供了可通过使用上述配制剂得到的种子。
此处,术语“涂有和/或含有”是指芳基甲酸联苯基酰胺I在施用时绝大部分在种子表面上,然而,取决于施用方法或多或少的部分芳基甲酸联苯基酰胺I可渗透入种子中。当(再)种植所述种子时,其可吸收芳基甲酸联苯基酰胺I。
本发明还进一步涉及种子,尤其是未播种的种子,其包含式I的芳基甲酸联苯基酰胺。
根据一个实施方案,这种包含式I的芳基甲酸联苯基酰胺的种子具有包衣,其中包衣包含芳基甲酸联苯基酰胺I。根据另一实施方案,这种包含芳基甲酸联苯基酰胺I的种子为其可萌发部分和/或其天然外壳、壳、荚或珠被包含芳基甲酸联苯基酰胺I的种子。芳基甲酸联苯基酰胺I也可同时存在于包衣和种子的可萌发部分和/或其天然外壳、壳、荚或珠被中。
优选这类种子包含有效量的芳基甲酸联苯基酰胺I。因此,以此方式包衣、浸渍或包衣并浸渍种子降低了萌发和出苗过程中的害虫损害。
用式I的芳基甲酸联苯基酰胺处理的种子也可用膜外涂层包封以保护芳基甲酸联苯基酰胺I包衣。该外涂层在本领域是已知的且可使用常规流化床和转鼓膜涂覆技术施加。
本发明种子可用于繁殖植物。可将种子储存、处理、种植/播种和耕作。
除非另有说明,所有以重量%表示的量涉及组合物(或配制剂)的总重量。
如下实施例进一步阐述本发明而不是限制本发明。
实施例
应用实施例1-对小麦上的小麦壳针孢的活性(种子处理)
将9.6mg活性化合物Ia.90溶于1ml丙酮得到储备溶液。用丙酮稀释储备溶液得到测试溶液。用丙酮稀释储备溶液得到测试溶液。将4.8g小麦种子试样置于玻璃瓶中,其中在空气流中用0.5ml含有活性化合物的测试溶液处理它们。在每种情况下,将10颗谷粒播种在8cm直径的盆中。将未处理谷粒用作对照。在播种后14天,用小麦壳针孢的孢子悬浮液对小麦植物接种。在接种24天后,以百分数目测侵染程度。结果汇集在表1中。浓度以g活性化合物(ga.i.)/100kg种子表示。
表1
应用实施例2-对小麦上的隐匿柄锈菌的活性(种子处理)
将24mg表2所列的活性化合物在每种情况下溶于1ml丙酮得到储备溶液。用丙酮稀释储备溶液得到测试溶液。将4.8g小麦种子试样置于玻璃瓶中,其中在空气流中用1ml含有活性化合物的测试溶液处理它们。在每种情况下,将10颗谷粒播种在8cm直径的盆中。将未处理谷粒用作对照。在播种后14天,用小麦壳针孢的孢子悬浮液对小麦植物接种。在接种7天后,以百分数目测侵染程度。结果汇集在表2中。浓度以g活性化合物(g a.i.)/100kg种子表示。
表2
化合物 | 浓度[g a.i./100kg] | 侵染叶面积[%] |
对照 | - | 90 |
Ia.90 | 250 | 0 |
Ia.85 | 250 | 11 |
Ia.245 | 250 | 19 |
Ia.255 | 250 | 38 |
应用实施例3-对大豆上的豆薯层锈菌的活性(种子处理)
将16mg表3所列的活性化合物在每种情况下溶于1ml丙酮得到储备溶液。用丙酮稀释储备溶液得到测试溶液。将1.5g大豆种子试样置于玻璃瓶中,其中在空气流中用0.6ml含有活性化合物的测试溶液处理它们。在每种情况下,将8颗谷粒播种在8cm直径的盆中。将未处理谷粒用作对照。在播种后14天,用豆薯层锈菌的孢子悬浮液对大豆植物接种。在接种10天后,以百分数目测侵染程度。结果汇集在表3中。浓度以g活性化合物(g a.i.)/100kg种子表示。
表3
应用实施例4-对小麦上的小麦壳针孢的活性
将活性化合物在二甲亚砜中配制成浓度为10000ppm的储备溶液。用水将储备溶液稀释至所述活性化合物浓度。将1ml各溶液用移液管移至生长在蛭石中的小麦秧苗(每盆10-12颗秧苗)。处理7天后,用小麦壳针孢的孢子悬浮液对小麦植物接种。在接种18天后,以百分数目测侵染程度。结果汇集在表4中。浓度以g活性化合物(g a.i.)/100kg种子表示。
表4
应用实施例5-对小麦上的小麦壳针孢的活性
将活性化合物在丙酮中配制成浓度为10 000ppm的储备溶液。用水将储备溶液稀释至所述活性化合物浓度。将1ml各溶液用移液管移至生长在蛭石中的小麦秧苗(每盆10-12颗秧苗)。处理7天后,将5cm长的叶部分置于充满含水琼脂的皮氏培养皿中。然后用小麦壳针孢的孢子悬浮液对叶部分接种。将封闭的皮氏培养皿在气候测试箱中在18℃和每天12小时的光暴露下培养。在培养18天后,以百分数目测侵染程度。结果汇集在表5中。浓度以g活性化合物(g a.i.)/100kg种子表示。
表5
应用实施例6-对小麦上的隐匿柄锈菌的活性
将活性化合物在丙酮中配制成浓度为10 000ppm的储备溶液。用水将储备溶液稀释至所述活性化合物浓度。将1ml各溶液用移液管移至生长在蛭石中的小麦秧苗(每盆10-12颗秧苗)。处理7天后,用隐匿柄锈菌的孢子悬浮液对小麦植物接种。在接种7天后,以百分数目测侵染程度。结果汇集在表6中。浓度以g活性化合物(g a.i.)/100kg种子表示。
表6
应用实施例7-对小麦上的小麦禾白粉菌的活性
将活性化合物在丙酮中配制成浓度为10 000ppm的储备溶液。用水将储备溶液稀释至所述活性化合物浓度。将1ml各溶液用移液管移至生长在蛭石中的小麦秧苗(每盆10-12颗秧苗)。处理7天后,用小麦禾白粉菌的孢子悬浮液对小麦植物接种。在接种7天后,以百分数目测侵染程度。结果汇集在表7中。浓度以g活性化合物(g a.i.)/100kg种子表示。
表7
应用实施例8-对大豆上的豆薯层锈菌的活性
将活性化合物在二甲亚砜中配制成浓度为10 000ppm的储备溶液。用水将储备溶液稀释至所述活性化合物浓度。将1ml各溶液用移液管移至生长在蛭石中的大豆秧苗(每盆1颗秧苗)。处理7天后,用豆薯层锈菌的孢子悬浮液对大豆植物接种。在接种14天后,以百分数目测侵染程度。结果汇集在表8中。浓度以g活性化合物(g a.i.)/100kg种子表示。
表8
化合物 | 浓度[g a.i./100kg] | 侵染叶面积[%] |
对照 | - | 88 |
Id.1 | 250 | 40 |
Ia.90 | 250 | 0 |
Ia.110 | 250 | 17 |
Ia.211 | 250 | 3 |
Ia.245 | 250 | 0 |
Claims (37)
1.一种保护植物在萌发后免受叶面植物病原性真菌侵袭的方法,其包括用有效量的至少一种式I的芳基甲酸联苯基酰胺或其可农用盐处理由其生长植物的种子:
其中
X为卤素或甲基;
n为0、1或2,其中在n为2的情况下,基团X可具有相同或不同含义;
Y为氰基、硝基、卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4卤代烷硫基、C1-C4烷氧亚氨基甲基或烯丙氧基亚氨基甲基;
m为0-5,其中在m为2、3、4或5的情况下,基团Y可具有相同或不同含义;
Ar为式IIa、IIb或IIc的芳基:
其中
R1为氢、卤素、C1-C4烷基或C1-C4卤代烷基,
R2为C1-C4烷基,
R3为氢、卤素或甲基,
R4为氢、卤素或C1-C4烷基,
R5为C1-C4烷基或C1-C4卤代烷基,
Z为CH或N,和
R6为卤素、C1-C4烷基或C1-C4卤代烷基。
2.根据权利要求1的方法,其中Ar为式IIa的芳基。
3.根据权利要求2的方法,其中R1为C1-C2卤代烷基。
4.根据权利要求2或3的方法,其中R3为氢。
5.根据权利要求2-4中任一项的方法,其中Y选自卤素、C1-C4烷基、C1-C4卤代烷基和C1-C4卤代烷硫基且m为1、2或3。
6.根据权利要求2-5中任一项的方法,其中X为卤素且n为0或1。
7.根据权利要求1的方法,其中Ar为式IIb的芳基。
8.根据权利要求1的方法,其中Ar为其中X为N的式IIc的芳基。
9.根据权利要求8的方法,其中R6为卤素。
10.根据权利要求8或9的方法,其中n为0,Y为卤素且m为1。
11.根据权利要求1的方法,其中Ar为其中X为CH的式IIc的芳基。
12.一种保护植物在萌发后免受叶面植物病原性真菌侵袭的方法,其包括用有效量的至少一种根据权利要求1-11中任一项的式I的芳基甲酸联苯基酰胺与至少一种选自下列的杀真菌活性成分一起处理由其生长植物的种子:
·唑类,如糠菌唑、环唑醇、噁醚唑、氧唑菌、喹唑菌酮、氟硅唑、粉唑醇、己唑醇、烯菌灵、环戊唑菌、腈菌唑、戊菌唑、丙环唑、丙氯灵、丙硫菌唑、戊唑醇、氟醚唑、三唑酮、唑菌醇和戊叉唑菌;
·酰基丙氨酸类,如苯霜灵、甲霜灵、mefenoxam、甲呋酰胺和噁霜灵;
·胺衍生物如双胍盐;
·苯胺基嘧啶类,如二甲嘧菌胺、嘧菌胺和环丙嘧啶;
·二羧酰亚胺类,如异丙定、杀菌利或烯菌酮;
·二硫代氨基甲酸盐类,如代森锰锌、代森联和福美双;
·杂环化合物如苯菌灵、多菌灵、萎锈灵、氧化萎锈灵、麦穗宁、氟吡菌胺、吡噻菌胺、丙氧喹啉、涕必灵和甲基托布津;
·苯基吡咯类,如拌种咯或氟噁菌;
·其它杀真菌剂,如苯噻菌胺、环氟菌胺、藻菌磷、乙膦铝、亚磷酸及其盐、异丙菌胺、苯菌酮和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;
·嗜球果伞素类,如腈嘧菌酯、醚菌胺、enestrobin、烯肟菌酯、氟嘧菌酯、亚胺菌、叉氨苯酰胺、肟醚菌胺、啶氧菌酯、唑菌胺酯和肟菌酯、(2-氯-5-[1-(3-甲基苄氧亚氨基)乙基]苄基)氨基甲酸甲酯、(2-氯-5-[1-(6-甲基吡啶-2-基甲氧基亚氨基)乙基]苄基)氨基甲酸甲酯和2-邻-[(2,5-二甲基苯氧基亚甲基)苯基]-3-甲氧基丙烯酸甲酯;
·肉桂酰胺及类似化合物,如烯酰吗啉、氟联苯菌和氟吗啉。
13.一种保护植物在萌发后免受叶面植物病原性真菌侵袭的方法,其包括用有效量的至少一种根据权利要求1-11中任一项的式I的芳基甲酸联苯基酰胺与至少一种选自下列的杀虫活性成分一起处理由其生长植物的种子:吡虫清、甲体氯氰菊酯、乙体氯氰菊酯、氟氯菊酯、虫螨威、丁硫克百威、噻虫胺、乙氰菊酯、氟氯氰菊酯、氯氰菊酯、溴氰菊酯、氟脲杀、呋虫胺、醚菊酯、杀螨锡、甲氰菊酯、锐劲特、氟氰戊菊酯、吡虫啉、γ-氯氟氰菊酯、硝胺烯啶、信息激素、艾克敌105、伏虫隆、七氟菊酯、特丁磷、噻虫啉、噻虫嗪、硫双威、四溴菊酯、唑蚜威、己体氯氰菊酯、螺虫乙酯、吡氟硫磷、唑虫酰胺、氟虫酰胺、双三氟虫脲、benclothiaz、pyrafluprole、pyriprole、amidoflumet、flufenerim、丁氟螨酯、cyenopyrafen、Γ2的邻氨基苯甲酰胺化合物:
其中B1为Cl,B2为Br且RB为CH3;以及Γ2的邻氨基苯甲酰胺化合物,其中B1为CN、B2为Br且RB为CH3。
14.根据权利要求13的方法,其中所述杀虫活性成分选自锐劲特、吡虫啉、acetamipird、硝胺烯啶、虫螨威、丁硫克百威、丙硫克百威、噻虫啉、噻虫胺、呋虫胺和噻虫嗪。
15.根据权利要求1-14中任一项的方法,其中所述种子为块茎蔬菜或玉米蔬菜、叶蔬菜、叶菜小棠菜或果实蔬菜的种子。
16.根据权利要求1-14中任一项的方法,其中所述种子为豆科植物的种子。
17.根据权利要求16的方法,其中所述种子为大豆种子。
18.根据权利要求1-14中任一项的方法,其中所述种子为禾谷类的种子。
19.根据权利要求1-18中任一项的方法,其中用于保护处于生长阶段09(BBCH扩充版)或更高生长阶段的植物。
20.根据权利要求1-19中任一项的方法,其中所述有效量为1-500g/100kg种子。
21.根据权利要求1-20中任一项的方法,其中所述处理为拌种。
22.一种包含至少一种根据权利要求1-11中任一项的式(I)的芳基甲酸联苯基酰胺和至少一种种子处理助剂的种子处理配制剂。
23.根据权利要求22的配制剂,其包含0.005-95重量%至少一种芳基甲酸联苯基酰胺I。
24.根据权利要求22或23的配制剂,其中所述配制剂包含至少一种选自下列的杀真菌活性成分:
·唑类,如糠菌唑、环唑醇、噁醚唑、氧唑菌、喹唑菌酮、氟硅唑、粉唑醇、己唑醇、烯菌灵、环戊唑菌、腈菌唑、戊菌唑、丙环唑、丙氯灵、丙硫菌唑、戊唑醇、氟醚唑、三唑酮、唑菌醇和戊叉唑菌;
·酰基丙氨酸类,如苯霜灵、甲霜灵、mefenoxam、甲呋酰胺和噁霜灵;
·胺衍生物如双胍盐;
·苯胺基嘧啶类,如二甲嘧菌胺、嘧菌胺和环丙嘧啶;
·二羧酰亚胺类,如异丙定、杀菌利或烯菌酮;
·二硫代氨基甲酸盐类,如代森锰锌、代森联和福美双;
·杂环化合物如苯菌灵、多菌灵、萎锈灵、氧化萎锈灵、麦穗宁、氟吡菌胺、吡噻菌胺、丙氧喹啉、涕必灵和甲基托布津;
·苯基吡咯类,如拌种咯或氟噁菌;
·其它杀真菌剂,如苯噻菌胺、环氟菌胺、藻菌磷、乙膦铝、亚磷酸及其盐、异丙菌胺、苯菌酮和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;
·嗜球果伞素类,如腈嘧菌酯、醚菌胺、enestrobin、烯肟菌酯、氟嘧菌酯、亚胺菌、叉氨苯酰胺、肟醚菌胺、啶氧菌酯、唑菌胺酯和肟菌酯、(2-氯-5-[1-(3-甲基苄氧亚氨基)乙基]苄基)氨基甲酸甲酯、(2-氯-5-[1-(6-甲基吡啶-2-基甲氧基亚氨基)乙基]苄基)氨基甲酸甲酯和2-邻-[(2,5-二甲基苯氧基亚甲基)苯基]-3-甲氧基丙烯酸甲酯;
·肉桂酰胺及类似化合物,如烯酰吗啉、氟联苯菌和氟吗啉。
25.根据权利要求22或23的配制剂,其中所述配制剂包含至少一种选自下列的杀虫活性成分:
吡虫清、甲体氯氰菊酯、乙体氯氰菊酯、氟氯菊酯、虫螨威、丁硫克百威、噻虫胺、乙氰菊酯、氟氯氰菊酯、氯氰菊酯、溴氰菊酯、氟脲杀、呋虫胺、醚菊酯、杀螨锡、甲氰菊酯、锐劲特、氟氰戊菊酯、吡虫啉、γ-氯氟氰菊酯、硝胺烯啶、信息激素、艾克敌105、伏虫隆、七氟菊酯、特丁磷、噻虫啉、噻虫嗪、硫双威、四溴菊酯、唑蚜威、己体氯氰菊酯、螺虫乙酯、吡氟硫磷、唑虫酰胺、氟虫酰胺、双三氟虫脲、benclothiaz、pyrafluprole、pyriprole、amidoflumet、flufenerim、丁氟螨酯、cyenopyrafen、Γ2的邻氨基苯甲酰胺化合物:
其中B1为Cl,B2为Br且RB为CH3;以及Γ2的邻氨基苯甲酰胺化合物,其中B1为CN、B2为Br且RB为CH3。
26.根据权利要求25的配制剂,其中所述杀虫活性成分选自锐劲特、吡虫啉、acetamipird、硝胺烯啶、虫螨威、丁硫克百威、丙硫克百威、噻虫啉、噻虫胺、呋虫胺和噻虫嗪。
27.根据权利要求22-26中任一项的配制剂,其中所述配制剂包含哺乳动物/鸟类驱除剂。
28.根据权利要求22的配制剂,其中所述种子处理助剂为种子包衣助剂、固体基质材料、渗透改进剂、着色剂、防冻剂和/或胶凝剂。
29.根据权利要求28的配制剂,其中所述种子包衣助剂为粘合剂。
30.一种用根据权利要求1-21中任一项的方法处理的种子。
31.种子,其包含至少一种根据权利要求1-11中任一项的式I的芳基甲酸联苯基酰胺和任选的至少一种选自下列的杀真菌活性成分:
·唑类,如糠菌唑、环唑醇、噁醚唑、氧唑菌、喹唑菌酮、氟硅唑、粉唑醇、己唑醇、烯菌灵、环戊唑菌、腈菌唑、戊菌唑、丙环唑、丙氯灵、丙硫菌唑、戊唑醇、氟醚唑、三唑酮、唑菌醇和戊叉唑菌;
·酰基丙氨酸类,如苯霜灵、甲霜灵、mefenoxam、甲呋酰胺和噁霜灵;
·胺衍生物如双胍盐;
·苯胺基嘧啶类,如二甲嘧菌胺、嘧菌胺或环丙嘧啶;
·二羧酰亚胺类,如异丙定、杀菌利或烯菌酮;
·二硫代氨基甲酸盐类,如代森锰锌、代森联和福美双;
·杂环化合物如苯菌灵、多菌灵、萎锈灵、氧化萎锈灵、麦穗宁、氟吡菌胺、吡噻菌胺、丙氧喹啉、涕必灵和甲基托布津;
·苯基吡咯类,如拌种咯或氟噁菌;
·其它杀真菌剂,如苯噻菌胺、环氟菌胺、藻菌磷、乙膦铝、亚磷酸及其盐、异丙菌胺、苯菌酮和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;
·嗜球果伞素类,如腈嘧菌酯、醚菌胺、enestrobin、烯肟菌酯、氟嘧菌酯、亚胺菌、叉氨苯酰胺、肟醚菌胺、啶氧菌酯、唑菌胺酯和肟菌酯、(2-氯-5-[1-(3-甲基苄氧亚氨基)乙基]苄基)氨基甲酸甲酯、(2-氯-5-[1-(6-甲基吡啶-2-基甲氧基亚氨基)乙基]苄基)氨基甲酸甲酯和2-邻-[(2,5-二甲基苯氧基亚甲基)苯基]-3-甲氧基丙烯酸甲酯;
·肉桂酰胺及类似化合物,如烯酰吗啉、氟联苯菌和氟吗啉,和/或至少一种选自下列的杀虫活性成分:吡虫清、甲体氯氰菊酯、乙体氯氰菊酯、氟氯菊酯、虫螨威、丁硫克百威、噻虫胺、乙氰菊酯、氟氯氰菊酯、氯氰菊酯、溴氰菊酯、氟脲杀、呋虫胺、醚菊酯、杀螨锡、甲氰菊酯、锐劲特、氟氰戊菊酯、吡虫啉、γ-氯氟氰菊酯、硝胺烯啶、信息激素、艾克敌105、伏虫隆、七氟菊酯、特丁磷、噻虫啉、噻虫嗪、硫双威、四溴菊酯、唑蚜威、己体氯氰菊酯、螺虫乙酯、吡氟硫磷、唑虫酰胺、氟虫酰胺、双三氟虫脲、benclothiaz、pyrafluprole、pyriprole、amidoflumet、flufenerim、丁氟螨酯、cyenopyrafen、Γ2的邻氨基苯甲酰胺化合物:
其中B1为Cl,B2为Br且RB为CH3;以及Γ2的邻氨基苯甲酰胺化合物,其中B1为CN、B2为Br且RB为CH3。
32.根据权利要求30或31的种子,其中所述种子具有包衣,该包衣包含至少一种根据权利要求1-11中任一项的式I的芳基甲酸联苯基酰胺和任选的至少一种选自下列的杀真菌活性成分:
·唑类,如糠菌唑、环唑醇、噁醚唑、氧唑菌、喹唑菌酮、氟硅唑、粉唑醇、己唑醇、烯菌灵、环戊唑菌、腈菌唑、戊菌唑、丙环唑、丙氯灵、丙硫菌唑、戊唑醇、氟醚唑、三唑酮、唑菌醇和戊叉唑菌;
·酰基丙氨酸类,如苯霜灵、甲霜灵、mefenoxam、甲呋酰胺和噁霜灵;
·胺衍生物如双胍盐;
·苯胺基嘧啶类,如二甲嘧菌胺、嘧菌胺或环丙嘧啶;
·二羧酰亚胺类,如异丙定、杀菌利或烯菌酮;
·二硫代氨基甲酸盐类,如代森锰锌、代森联和福美双;
·杂环化合物如苯菌灵、多菌灵、萎锈灵、氧化萎锈灵、麦穗宁、氟吡菌胺、吡噻菌胺、丙氧喹啉、涕必灵和甲基托布津;
·苯基吡咯类,如拌种咯或氟噁菌;
·其它杀真菌剂,如苯噻菌胺、环氟菌胺、藻菌磷、乙膦铝、亚磷酸及其盐、异丙菌胺、苯菌酮和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;
·嗜球果伞素类,如腈嘧菌酯、醚菌胺、enestrobin、烯肟菌酯、氟嘧菌酯、亚胺菌、叉氨苯酰胺、肟醚菌胺、啶氧菌酯、唑菌胺酯和肟菌酯、(2-氯-5-[1-(3-甲基苄氧亚氨基)乙基]苄基)氨基甲酸甲酯、(2-氯-5-[1-(6-甲基吡啶-2-基甲氧基亚氨基)乙基]苄基)氨基甲酸甲酯和2-邻-[(2,5-二甲基苯氧基亚甲基)苯基]-3-甲氧基丙烯酸甲酯;
·肉桂酰胺及类似化合物,如烯酰吗啉、氟联苯菌和氟吗啉,和/或至少一种选自下列的杀虫活性成分:吡虫清、甲体氯氰菊酯、乙体氯氰菊酯、氟氯菊酯、虫螨威、丁硫克百威、噻虫胺、乙氰菊酯、氟氯氰菊酯、氯氰菊酯、溴氰菊酯、氟脲杀、呋虫胺、醚菊酯、杀螨锡、甲氰菊酯、锐劲特、氟氰戊菊酯、吡虫啉、γ-氯氟氰菊酯、硝胺烯啶、信息激素、艾克敌105、伏虫隆、七氟菊酯、特丁磷、噻虫啉、噻虫嗪、硫双威、四溴菊酯、唑蚜威、己体氯氰菊酯、螺虫乙酯、吡氟硫磷、唑虫酰胺、氟虫酰胺、双三氟虫脲、benclothiaz、pyrafluprole、pyriprole、amidoflumet、flufenerim、丁氟螨酯、cyenopyrafen、Γ2的邻氨基苯甲酰胺化合物:
其中B1为Cl,B2为Br且RB为CH3;以及Γ2的邻氨基苯甲酰胺化合物,其中B1为CN、B2为Br且RB为CH3。
33.根据权利要求31或32的种子,其中所述至少一种杀虫活性成分选自锐劲特、吡虫啉、acetamipird、硝胺烯啶、虫螨威、丁硫克百威、丙硫克百威、噻虫啉、噻虫胺、呋虫胺和噻虫嗪。
34.至少一种如权利要求1-11中任一项所定义的式I的芳基甲酸联苯基酰胺在处理种子以保护由该种子生长的植物在萌发后免受叶面植物病原性真菌侵袭中的用途。
35.根据权利要求34的用途,其中将至少一种式I的芳基甲酸联苯基酰胺与如下成分一起使用:至少一种选自下列的杀真菌活性成分:
·唑类,如糠菌唑、环唑醇、噁醚唑、氧唑菌、喹唑菌酮、氟硅唑、粉唑醇、己唑醇、烯菌灵、环戊唑菌、腈菌唑、戊菌唑、丙环唑、丙氯灵、丙硫菌唑、戊唑醇、氟醚唑、三唑酮、唑菌醇和戊叉唑菌;
·酰基丙氨酸类,如苯霜灵、甲霜灵、mefenoxam、甲呋酰胺和噁霜灵;
·胺衍生物如双胍盐;
·苯胺基嘧啶类,如二甲嘧菌胺、嘧菌胺和环丙嘧啶;
·二羧酰亚胺类,如异丙定、杀菌利或烯菌酮;
·二硫代氨基甲酸盐类,如代森锰锌、代森联和福美双;
·杂环化合物如苯菌灵、多菌灵、萎锈灵、氧化萎锈灵、麦穗宁、氟吡菌胺、吡噻菌胺、丙氧喹啉、涕必灵和甲基托布津;
·苯基吡咯类,如拌种咯或氟噁菌;
·其它杀真菌剂,如苯噻菌胺、环氟菌胺、藻菌磷、乙膦铝、亚磷酸及其盐、异丙菌胺、苯菌酮和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;
·嗜球果伞素类,如腈嘧菌酯、醚菌胺、enestrobin、烯肟菌酯、氟嘧菌酯、亚胺菌、叉氨苯酰胺、肟醚菌胺、啶氧菌酯、唑菌胺酯和肟菌酯、(2-氯-5-[1-(3-甲基苄氧亚氨基)乙基]苄基)氨基甲酸甲酯、(2-氯-5-[1-(6-甲基吡啶-2-基甲氧基亚氨基)乙基]苄基)氨基甲酸甲酯和2-邻-[(2,5-二甲基苯氧基亚甲基)苯基]-3-甲氧基丙烯酸甲酯;
·肉桂酰胺及类似化合物,如烯酰吗啉、氟联苯菌和氟吗啉,和/或至少一种选自下列的杀虫活性成分:吡虫清、甲体氯氰菊酯、乙体氯氰菊酯、氟氯菊酯、虫螨威、丁硫克百威、噻虫胺、乙氰菊酯、氟氯氰菊酯、氯氰菊酯、溴氰菊酯、氟脲杀、呋虫胺、醚菊酯、杀螨锡、甲氰菊酯、锐劲特、氟氰戊菊酯、吡虫啉、γ-氯氟氰菊酯、硝胺烯啶、信息激素、艾克敌105、伏虫隆、七氟菊酯、特丁磷、噻虫啉、噻虫嗪、硫双威、四溴菊酯、唑蚜威、己体氯氰菊酯、螺虫乙酯、吡氟硫磷、唑虫酰胺、氟虫酰胺、双三氟虫脲、benclothiaz、pyrafluprole、pyriprole、amidoflumet、flufenerim、丁氟螨酯、cyenopyrafen、Γ2的邻氨基苯甲酰胺化合物:
其中B1为Cl,B2为Br且RB为CH3;以及Γ2的邻氨基苯甲酰胺化合物,其中B1为CN、B2为Br且RB为CH3,
锐劲特、吡虫啉、acetamipird、硝胺烯啶、虫螨威、丁硫克百威、丙硫克百威、噻虫啉、噻虫胺、MTI 446和CGA 293343。
36.根据权利要求35的用途,其中所述至少一种杀虫活性成分选自锐劲特、吡虫啉、acetamipird、硝胺烯啶、虫螨威、丁硫克百威、丙硫克百威、噻虫啉、噻虫胺、呋虫胺和噻虫嗪。
37.根据权利要求34-36中任一项的用途,其中用于保护处于生长阶段BBCH 09或更高生长阶段的植物免受植物病原性真菌侵袭。
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- 2007-05-02 EP EP07728718A patent/EP2020854A1/en not_active Withdrawn
- 2007-05-02 KR KR1020087029461A patent/KR20090011008A/ko not_active Application Discontinuation
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Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
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CN102781233A (zh) * | 2010-03-04 | 2012-11-14 | 巴斯夫欧洲公司 | 协同增效杀真菌混合物 |
CN103391925A (zh) * | 2010-11-15 | 2013-11-13 | 拜耳知识产权有限责任公司 | 5-卤代吡唑甲酰胺 |
CN103391925B (zh) * | 2010-11-15 | 2017-06-06 | 拜耳知识产权有限责任公司 | 5‑卤代吡唑甲酰胺 |
CN103503896A (zh) * | 2012-12-05 | 2014-01-15 | 江苏辉丰农化股份有限公司 | 具有增效作用的杀虫组合物 |
CN103999865A (zh) * | 2013-04-07 | 2014-08-27 | 海南正业中农高科股份有限公司 | 一种含有环氟菌胺与烯酰吗啉或苯酰菌胺的杀菌组合物及应用 |
CN103999865B (zh) * | 2013-04-07 | 2016-04-13 | 海南正业中农高科股份有限公司 | 一种含有环氟菌胺与烯酰吗啉或苯酰菌胺的杀菌组合物及应用 |
CN105555139A (zh) * | 2013-07-22 | 2016-05-04 | 住友化学株式会社 | 植物病害防治组合物及其用途 |
US9781931B2 (en) | 2013-07-22 | 2017-10-10 | Sumitomo Chemical Company, Limited | Plant disease control composition and its use |
CN104292156A (zh) * | 2014-10-15 | 2015-01-21 | 江苏耕耘化学有限公司 | 啶酰菌胺同系物、其非偶联法合成方法及其在制备防治病菌药物中的应用 |
CN104488878A (zh) * | 2014-10-30 | 2015-04-08 | 东莞市瑞德丰生物科技有限公司 | 杀菌组合物 |
CN108349895A (zh) * | 2015-09-07 | 2018-07-31 | 拜耳作物科学股份公司 | 取代的2-二氟甲基-烟碱(硫代)甲酰苯胺衍生物及其作为杀真菌剂的用途 |
Also Published As
Publication number | Publication date |
---|---|
JP5227950B2 (ja) | 2013-07-03 |
MA30483B1 (fr) | 2009-06-01 |
ECSP088858A (es) | 2008-12-30 |
PE20080252A1 (es) | 2008-05-11 |
AR060749A1 (es) | 2008-07-10 |
IL194958A0 (en) | 2009-08-03 |
EP2020854A1 (en) | 2009-02-11 |
UA91612C2 (ru) | 2010-08-10 |
NZ572258A (en) | 2011-09-30 |
CN101484009B (zh) | 2013-08-07 |
UY30323A1 (es) | 2007-10-31 |
US20090264289A1 (en) | 2009-10-22 |
CR10381A (es) | 2008-11-26 |
EA016506B1 (ru) | 2012-05-30 |
KR20090011008A (ko) | 2009-01-30 |
ZA200810194B (en) | 2011-05-25 |
MX2008013854A (es) | 2009-01-26 |
WO2007128756A1 (en) | 2007-11-15 |
EA200802186A1 (ru) | 2009-04-28 |
BRPI0710774A2 (pt) | 2011-06-21 |
CL2007001253A1 (es) | 2008-01-25 |
CA2649925A1 (en) | 2007-11-15 |
TW200810694A (en) | 2008-03-01 |
AU2007247136A1 (en) | 2007-11-15 |
JP2009535379A (ja) | 2009-10-01 |
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