CN113710091A - 硫酮的稳定制剂 - Google Patents
硫酮的稳定制剂 Download PDFInfo
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- CN113710091A CN113710091A CN202080030480.XA CN202080030480A CN113710091A CN 113710091 A CN113710091 A CN 113710091A CN 202080030480 A CN202080030480 A CN 202080030480A CN 113710091 A CN113710091 A CN 113710091A
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- prothioconazole
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- A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
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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
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- A—HUMAN NECESSITIES
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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
- A01N37/36—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 at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
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Abstract
本发明涉及具有特定抗氧化剂并且具有特别低2‑(1‑氯环丙基)‑1‑(2‑氯苯基)‑3‑(1H‑1,2,4‑三唑‑1‑基)丙‑2‑醇含量的储存稳定的含有丙硫菌唑的制剂,用于制备其的方法,用于防治植物病原性真菌以保护作物的方法,以及其作为作物保护剂的用途。
Description
本发明涉及硫酮(thiones)的稳定制剂、特别是含有硫酮结构单元、尤其是三唑啉硫酮作为官能团的活性成分的稳定制剂。
本发明特别涉及储存稳定的含有硫酮的制剂,例如丙硫菌唑(prothioconazole)或4-((6-(2-(2,4-二氟苯基)-1,1-二氟-2-羟基-3-(5-巯基-1H-1,2,4-三唑-l-基)丙基)吡啶-3-基)氧基)苯甲腈,该制剂具有特别低含量的相应的脱硫化合物,例如2-(1-氯环丙基)-1-(2-氯苯基)-3-(1H-1,2,4-三唑-1-基)丙-2-醇。
本发明还涉及制备上述制剂的方法,涉及用于在作物保护中防治植物病原性真菌的方法,以及涉及所述制剂作为作物保护组合物的用途。
此外,本发明涉及包含某些抗氧化剂的制剂,特别是包含维生素C(抗坏血酸)和/或生育酚(维生素E)的制剂、硫酮化合物的制剂、特别是具有硫酮基团的农业化学活性成分的制剂,以及涉及某些抗氧化剂、特别是维生素C和生育酚(维生素E)用于稳定硫酮化合物、特别是具有硫酮基团的农业化学活性成分的用途。
已知的是,例如,丙硫菌唑可以用于防治真菌的标准制剂中(WO-A 96/16 048)。该活性成分是2-[2-(1-氯环丙基)-3-(2-氯苯基)-2-羟基丙基]-2,4-二氢-3H-1,2,4-三唑-3-硫酮。含有丙硫菌唑的制剂通常是液体制剂,并且例如以乳液浓缩物的形式在市场上供应。
此外,已知活性成分丙硫菌唑可以在特定条件下降解,以得到化合物2-(1-氯环丙基)-1-(2-氯苯基)-3-(1H-1,2,4-三唑-1-基)丙-2-醇(PSM-Zulassungsbericht[CropProtection Agent Registration Report],Tilmor,2010.08.30,系列号21,德国消费者保护和食品安全联邦局(German Federal Office of Consumer Protection and FoodSafety))。
因此,早在制备过程中,含有丙硫菌唑(下文称为PTZ)的制剂就可能含有一定量的2-(1-氯环丙基)-1-(2-氯苯基)-3-(1H-1,2,4-三唑-1-基)丙-2-醇。在苛刻条件,例如高温、光入射和强烈的氧气接触下储存的情况下,同样可能发生丙硫菌唑的降解,以得到2-(1-氯环丙基)-1-(2-氯苯基)-3-(1H-1,2,4-三唑-1-基)丙-2-醇,由此制剂中的活性成分的含量相应地降低。由于化合物2-(1-氯环丙基)-1-(2-氯苯基)-3-(1H-1,2,4-三唑-1-基)丙-2-醇(下文称为脱硫物)是相关杂质,因此其在含有丙硫菌唑的制剂中的含量受法规限制。这也类似地适用于其它含硫酮的化合物,例如4-((6-(2-(2,4-二氟苯基)-1,1-二氟-2-羟基-3-(5-巯基-1H-1,2,4-三唑-l-基)丙基)吡啶-3-基)氧基)苯甲腈。
这里,PTZ制剂中的脱硫物的最大允许量取决于制剂中的PTZ以g/L计的量。脱硫物的最大允许量以ppm给出,其中脱硫物以ppm计的允许含量是PTZ负载以g/L计的值的一半。因此,在具有100g/L PTZ的制剂中的最大允许的脱硫物含量为50ppm(=0.005重量%)。
WO-A 2012/033590公开了含有含硫化合物,例如L-半胱氨酸以进行稳定化的丙硫菌唑水分散体。
WO 2017/097882和WO2018/228885记载了稳定的含有PTZ的制剂,其可被视为最接近的现有技术。其中记载了包含溶解于溶剂中的PTZ的乳液浓缩物和悬浮浓缩物。可以通过添加式(I)的化合物来使制剂稳定化,并实现脱硫物含量的降低
其中
n代表3、4、5、6、7、8、9、10、11、12、15或18。
式(I)的化合物由WO-A 2012/061094已知,并且可以通过复分解方法来制备。这些是例如来自Stepan的产品((N,N-二甲基9-癸烯酰胺,CAS号:1356964-77-6,1025或MET-10U)。
这些化合物具有这样的缺点:它们需要非常大量的最高达30%的稳定剂以达到所需效果,这代表了制剂的重大改进。此外,这些是新的添加剂,其中在一些情况下,仍然需要批准用于作物保护制剂中。
因此,需要稳定的包含PTZ的制剂,其即使在长时间和不利的储存条件下,例如暴露于氧气、高温或光的作用下,也有效地抑制或防止硫酮、特别是三唑啉硫酮的降解,尤其是抑制或防止PTZ降解成相应的脱硫产物,例如2-(1-氯环丙基)-1-(2-氯苯基)-3-(1H-1,2,4-三唑-1-基)丙-2-醇(化合物III),并且同时对于农业化学用途是可接受的或不面临任何监管障碍。
因此,本发明的一个目的是提供新型、改进的含有硫酮的制剂,其具有高储存稳定性并且不表现出硫酮降解成相应的脱硫产物、特别是丙硫菌唑降解成2-(1-氯环丙基)-1-(2-氯苯基)-3-(1H-1,2,4-三唑-1-基)丙-2-醇的任何显著降解速率。
此外,本发明的一个目的是提供用于硫酮的稳定剂和/或稳定剂体系,所述稳定剂适用于农业化学制剂,并且即使在少量时也非常有效。
此外,发现硫酮降解成脱硫产物容易被光、尤其是某些波长的光触发。然而,出人意料地发现,这里,常规UV阻断剂或UV吸收剂仅不足够有效。
此外,发现即使各种商业抗氧化剂也不能提供有效的保护以防止硫酮的降解,而是甚至促进降解。
出人意料地,已经发现,即使非常少量的某些抗氧化剂如抗坏血酸和生育酚(维生素E)也显著有效地防止硫酮、特别是丙硫菌唑降解成脱硫产物。
因此,本发明提供包含以下物质的制剂:
a)具有硫酮基团的活性成分、优选农业化学活性成分,和
b)至少一种选自以下抗氧化剂的化合物:抗坏血酸、生育三烯酚、生育酚(例如(+)-δ-生育酚、(+/-)-α-生育酚)、生育酚的混合物、硫代乳酸、丁羟甲苯BHT、丁子香酚、咖啡酸(3,4-二羟基肉桂酸)、巯基丙酸和D,L-硫苏糖醇,以及这些化合物的混合物。
所述制剂优选为农业化学制剂。
在另一个优选的实施方案中,具有硫酮基团的活性成分a)选自丙硫菌唑和4-((6-(2-(2,4-二氟苯基)-1,1-二氟-2-羟基-3-(5-巯基-1H-1,2,4-三唑-l-基)丙基)吡啶-3-基)氧基)苯甲腈,特别优选仅丙硫菌唑。
此外,所述活性成分优选以1重量%至50重量%、更优选4重量%至30重量%并且特别优选5重量%至28重量%的量存在,基于所述制剂的总重量计。
抗氧化剂b)更优选选自维生素C(抗坏血酸)、生育酚和生育三烯酚(优选(+)-δ-生育酚、(+/-)-α-生育酚、(+)-α-生育酚和维生素E以及生育酚的混合物)。此外,在含水制剂中优选抗坏血酸,而在具有有机溶剂的制剂中优选生育酚。
维生素E是具有抗氧化作用的脂溶性物质的集合性术语,其中生育酚和生育三烯酚是最常遇到的形式。在下文中,术语维生素E意指包括α-生育酚(RRR-α-生育酚或D-α-T0)、β-生育酚、γ-生育酚、δ-生育酚、α-生育三烯酚、β-生育三烯酚、γ-生育三烯酚、δ-生育三烯酚,以及它们的衍生物,例如乙酸酯。
独立于制剂类型,抗氧化剂优选以0.01重量%至15.00重量%、更优选0.03重量%至5.00重量%并且特别优选0.2重量%至4重量%的量存在,基于制剂的总重量计。
取决于制剂,例如水基的或油基的制剂,优选使用水溶性或油溶性抗氧化剂,优选以以下量:
SC制剂:
在SC中,抗氧化剂优选以0.01重量%至10.00重量%、更优选0.03重量%至5重量%、甚至更优选0.03重量%至1.00重量%并且特别优选0.05重量%至0.5重量%的量存在,基于制剂的总重量计。
OD制剂和EC制剂:
在OD中,抗氧化剂优选以0.10重量%至5.00重量%、更优选0.2重量%至4.00重量%并且特别优选0.2重量%至3重量%的量存在,基于制剂的总重量计。
在EC中,抗氧化剂优选以0.50重量%至15.00重量%、更优选1重量%至10.00重量%并且特别优选3重量%至10重量%的量存在,基于制剂的总重量计。
丙硫菌唑(具有化学名2-[2-(1-氯环丙基)-3-(2-氯苯基)-2-羟基丙基]-1,2-二氢-3H-1,2,4-三唑-3-硫酮)(CAS号178928-70-6)以外消旋体形式存在。其合适的制备方法记载于DE-A 195280中。丙硫菌唑可以以通式(II)的硫羰形式存在,
或以通式(IIa)的互变异构巯基形式存在。
术语“丙硫菌唑”的使用在下文中总是涵盖本文所示的异构体和其它可能的互变异构体。
2-(1-氯环丙基)-1-(2-氯苯基)-3-(1H-1,2,4-三唑-1-基)丙-2-醇也作为外消旋体存在,并且具有通式(III),其中又应包含具有该表示的所有互变异构形式。
此外,如上所述,本发明的制剂可以各自包含另外的成分,例如:
c)c1:非离子型分散剂/乳化剂,
c2:离子型分散剂/乳化剂,
d)不同于a)的其它农业化学活性成分,
e)溶剂,包括OD载体,
f)载体(WG,以及用于SC/TK/WG的Aerosil),
g)g1:有机增稠剂,
g2:无机增稠剂,
h)其它添加剂和助剂。
制剂类型由FAO定义并在www.fao.org/ag/agp/agpp/pesticid找到。在2016年3月的版本中,第66-231页记载了常规制剂类型。本发明的制剂是FAO记载的常规制剂类型。本文中可以提及的实例是悬浮浓缩物(SC)、以及用于种子处理的含有着色剂的浓缩物(FS)、乳液浓缩物(EC)、水分散性浓缩物(WG)、油分散体(OD)、悬乳剂(SE)、水性乳液(EW)、微乳液(ME)和液体制剂(SL)。优选的是EC、SC、FS、SE、OD和WG制剂类型,非常特别优选其中至少一种活性成分不溶解的制剂。非常特别优选FS、SC、SE、OD和WG制剂,最优选SC、FS和WG制剂。
本发明还提供本发明的制剂用于处理植物的用途和相应的方法。
非离子型乳化剂和分散剂c1)
有用的非离子型乳化剂和分散剂c1),例如乳化剂、润湿剂、表面活性剂和分散剂,包括存在于农业化学活性成分的制剂中的标准表面活性物质。实例包括乙氧基化壬基酚、直链或支化醇与环氧乙烷和/或环氧丙烷的反应产物、环氧乙烷-环氧丙烷嵌段共聚物、端基封端和非端基封端的烷氧基化直链和支链的饱和和不饱和的醇(例如丁氧基聚乙二醇-聚丙二醇(butoxy polyethylenepropylene glycols))、烷基酚与环氧乙烷和/或环氧丙烷的反应产物、环氧乙烷-环氧丙烷嵌段共聚物、聚乙二醇和聚丙二醇,以及脂肪酸酯、脂肪酸聚二醇醚酯、烷基磺酸盐、烷基硫酸盐、芳基硫酸盐、乙氧基化芳基烷基酚,例如每分子具有平均16个环氧乙烷单元的三苯乙烯基酚-乙氧基化物、以及乙氧基化和丙氧基化芳基烷基酚、以及硫酸化或磷酸化的芳基烷基酚乙氧基化物或乙氧基-和丙氧基化物。特别优选三苯乙烯基酚烷氧基化物和脂肪酸聚二醇醚酯。非常特别优选三苯乙烯基酚乙氧基化物、三苯乙烯基酚-乙氧基-丙氧基化物和蓖麻油聚二醇醚酯,它们在每种情况下单独或混合使用。添加剂例如表面活性剂或脂肪酸酯可另外是有用的,其有助于提高生物功效。合适的非离子型乳化剂和分散剂c1)为例如796/P、CO30、HOT、PSI 100或T304。
合适的非离子型分散剂c1)同样可选自聚乙烯吡咯烷酮(PVP)、聚乙烯醇、PVP与甲基丙烯酸二甲基氨基乙酯的共聚物、丁基化的PVP、氯乙烯与乙酸乙烯酯的共聚物,以及部分水解的乙酸乙烯酯、酚醛树脂、改性纤维素类型,例如(聚乙烯吡咯烷酮)、(聚乙烯醇)或改性纤维素。优选聚乙烯吡咯烷酮类型,特别优选低分子量的类型,例如K30或K30。
有用的选自环氧烷烃的二嵌段和三嵌段共聚物的其它非离子型乳化剂和分散剂c1)为例如基于环氧乙烷和环氧丙烷的化合物,其平均摩尔质量为200至10000,优选1000至4000g/mol,其中聚乙氧基化嵌段的质量含量在10和80%之间变化,例如PE系列(Uniqema)、PE系列(BASF)、32或PF系列(Clariant)。
本发明的悬浮浓缩物中需要的非离子型乳化剂和分散剂c1)的含量为优选1重量%至15重量%,更优选2重量%至10重量%,且特别优选2.5重量%至8重量%。
阴离子型乳化剂和分散剂c2)
合适的阴离子型乳化剂和分散剂b1),例如乳化剂、表面活性剂、润湿剂和分散剂是例如磺酸、硫酸、磷酸、羧酸的碱金属盐、碱土金属盐或铵盐及其混合物,例如烷基磺酸或烷基磷酸和烷基芳基磺酸或烷基芳基磷酸的盐,二苯基磺酸盐、α-烯烃磺酸盐、木质素磺酸盐、脂肪酸和油的磺酸盐、乙氧基化烷基酚的磺酸盐、烷氧基化芳基酚的磺酸盐、缩合萘的磺酸盐、十二烷基苯或十三烷基苯的磺酸盐、萘和烷基萘的磺酸盐、磺基琥珀酸盐或磺基琥珀酰胺酸盐。硫酸盐的实例是脂肪酸和油、乙氧基化烷基酚、醇、乙氧基化醇或脂肪酸酯的硫酸盐。磷酸盐的实例是磷酸盐酯。羧酸盐的实例是烷基羧酸盐和羧化的醇乙氧基化物或烷基酚乙氧基化物。同样合适的是以下阴离子型乳化剂:聚苯乙烯磺酸的碱金属盐、碱土金属盐和铵盐、聚乙烯磺酸的盐、烷基萘磺酸的盐、烷基萘磺酸-甲醛缩合产物的盐,萘磺酸、苯酚磺酸和甲醛的缩合产物的盐。实例是十二烷基苯磺酸钙,例如70/B(Solvay)、Phenylsulfonat CA100(Clariant)或十二烷基苯磺酸异丙基铵,例如3300B(Croda)。
其它典型代表包括Phenylsulfonat CA(十二烷基苯磺酸钙)、产品(三苯乙烯基酚乙氧基化物的任选酯化衍生物)、3510(烷基化EO/PO共聚物)、EL 400(乙氧基化蓖麻油)、产品(脂肪酰化脱水山梨醇乙氧基化物)、AR 100(十二烷基苯磺酸钙)。优选烷基化芳族磺酸的盐与环氧乙烷和环氧丙烷的烷基化共聚物的组合,所述烷基化芳族磺酸的盐为例如苯磺酸钙和/或AR 100,所述环氧乙烷和环氧丙烷的烷基化共聚物为例如3510。特别优选十二烷基苯磺酸的盐与环氧乙烷和环氧丙烷的烷基化共聚物的组合,所述十二烷基苯磺酸的盐为例如AR 100,所述环氧乙烷和环氧丙烷的烷基化共聚物为例如3510。
选自萘磺酸盐的其它阴离子型乳化剂和分散剂c2)的实例是MT 800(二丁基萘磺酸钠)、IP(二异丙基萘磺酸钠)和BX(烷基萘磺酸盐)。选自萘磺酸盐与甲醛的缩合物的阴离子型表面活性剂的实例是DT 201(与甲醛和甲基酚钠盐的萘磺酸羟基聚合物)、DT 250(苯酚磺酸盐和萘磺酸盐的缩合产物)、C(苯酚磺酸盐和萘磺酸盐的缩合物)或D-425、2020。优选1,2-二丁基-或-二异丁基取代的萘磺酸盐,例如产品例如MT 800(CFPI-Nufarm)和BX(BASF)。其它典型的表面活性剂是3D33、4D384、BSU、CY/8(Solvay)和S3474,以及以T产品(Clariant)的形式,例如T 100。
本发明的技术浓缩物中需要的阴离子型乳化剂和分散剂c2)的含量为优选2重量%至35重量%,更优选3重量%至30重量%,甚至更优选5重量%至25重量%,且特别优选10重量%至20重量%。
本发明的悬浮浓缩物中需要的阴离子型乳化剂和分散剂c2)的含量为优选0.1重量%至10重量%,更优选0.2重量%至7重量%,且特别优选0.3重量%至4重量%。
不同于PTZ的其它农业化学活性成分d):
在本发明的上下文中,其它农业化学活性成分d)是杀真菌、杀虫或除草活性成分。在一个可替代的实施方案中,本发明的制剂包含一种或多种其它杀虫或杀真菌活性成分d),更优选一种或多种杀真菌活性成分d)。所使用的活性成分优选是水不溶性的。
农药手册(Pesticide Manual)提供了典型的作物保护剂的综述。
优选的杀虫组分d)为例如吡虫啉(imidacloprid)、烯啶虫胺(nitenpyram)、啶虫脒(acetamiprid)、噻虫啉(thiacloprid)、噻虫嗪(thiamethoxam)、噻虫胺(clothianidin)、氰虫酰胺(cyantraniliprole)、氯虫苯甲酰胺(chlorantraniliprole)、氟虫双酰胺(flubendiamide)、氟氰虫酰胺(tetraniliprole)、环溴虫酰胺(cyclaniliprole)、螺螨酯(spirodiclofen)、螺甲螨酯(spiromesifen)、螺虫乙酯(spirotetramat)、阿巴美丁(abamectin)、氟丙菊酯(acrinathrin)、溴虫腈(chlorfenapyr)、埃玛菌素(emamectin)、乙虫腈(ethiprole)、氟虫腈(fipronil)、氟啶虫酰胺(flonicamid)、氟吡呋喃酮(flupyradifurone)、茚虫威(indoxacarb)、氰氟虫腙(metaflumizone)、甲氧虫酰肼(methoxyfenozide)、米尔倍霉素(milbemycin)、哒螨灵(pyridaben)、啶虫丙醚(pyridalyl)、氟硅菊酯(silafluofen)、多杀菌素(spinosad)、氟啶虫胺腈(sulfoxaflor)、杀虫脲(triflumuron)、来自WO 2006/089633的作为实施例I-1-a-4的化合物、WO 2008/067911中作为实施例I-1-a-4公开的化合物、WO 2013/092350中作为实施例Ib-14公开的化合物、WO 2010/51926中作为实施例Ik-84公开的化合物。
优选的杀真菌组分d)为例如联苯吡菌胺(bixafen)、二氯异噁草酮(bixlozone)、咪唑菌酮(fenamidone)、环酰菌胺(fenhexamid)、氟吡菌胺(fluopicolide)、氟吡菌酰胺(fluopyram)、氟嘧菌酯(fluoxastrobin)、异丙菌胺(isoflucypram)、异丙菌胺(iprovalicarb)、异噻菌胺(isotianil)、异吡唑萘菌胺(isopyrazam)、戊菌隆(pencycuron)、氟唑菌苯胺(penflufen)、丙森锌(propineb)、戊唑醇(tebuconazole)、肟菌酯(trifloxystrobin)、唑嘧菌胺(ametoctradin)、吲唑磺菌胺(amisulbrom)、嘧菌酯(azoxystrobin)、苯噻菌胺(benthiavalicarb-isopropyl)、苯并烯氟菌唑(benzovindiflupyr)、啶酰菌胺(boscalid)、多菌灵(carbendazim)、chlorothanonil、氰霜唑(cyazofamid)、环氟菌胺(cyflufenamid)、霜脲氰(cymoxanil)、环唑醇(cyproconazole)、苯醚甲环唑(difenoconazole)、噻唑菌胺(ethaboxam)、氟环唑(epoxiconazole)、恶唑菌酮(famoxadone)、氟啶胺(fluazinam)、氟喹唑(fluquinconazole)、氟硅唑(flusilazole)、flutianil、氟唑菌酰胺(fluxapyroxad)、吡唑萘菌胺(isopyrazam)、醚菌酯(kresoxim-methyl)、lyserphenvalpyr、代森锰锌(mancozeb)、双炔酰菌胺(mandipropamid)、咪康唑(metconazol)、pyriofenone、灭菌丹(folpet)、苯氧菌胺(metaminostrobin)、氟噻唑吡乙酮(oxathiapiprolin)、吡噻菌胺(penthiopyrad)、啶氧菌酯(picoxystrobin)、烯丙异噻唑(probenazole)、丙氧喹啉(proquinazid)、氟唑菌酰羟胺(pydiflumetofen)、吡唑醚菌酯(pyraclostrobin)、氟唑环菌胺(sedaxane)、螺菌胺(spiroxamin)、tebufloquin、氟醚唑(tetraconazole)、valiphenalate、苯酰菌胺(zoxamide)、福美锌(ziram)、N-(5-氯-2-异丙基苄基)-N-环丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、N-(5-氯-2-异丙基苄基)-N-环丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、甲磺酸2-{3-[2-(1-{[3,5-双(二氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氢-1,2-噁唑-5-基}苯酯、甲磺酸2-{3-[2-(1-{[3,5-双(二氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氢-1,2-噁唑-5-基}-3-氯苯酯、2-甲基丙酸(3S,6S,7R,8R)-8-苄基-3-[({3-[(异丁酰基氧基)甲氧基]-4-甲氧基吡啶-2-基}羰基)氨基]-6-甲基-4,9-二氧代-1,5-二氧杂环壬烷-7-基酯(lyserphenvalpyr)。
丙硫菌唑的特别优选的杀真菌混合配对物d)是例如:戊唑醇、螺菌胺、联苯吡菌胺、氟嘧菌酯、肟菌酯、N-(5-氯-2-异丙基苄基)-N-环丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、2-甲基丙酸(3S,6S,7R,8R)-8-苄基-3-[({3-[(异丁酰基氧基)甲氧基]-4-甲氧基吡啶-2-基}羰基)氨基]-6-甲基-4,9-二氧代-1,5-二氧杂环壬烷-7-基酯(lyserphenvalpyr)和氟吡菌酰胺。
非常特别优选a)(丙硫菌唑)与一种或多种选自化合物d)的化合物的混合物:
a)+d)戊唑醇;
a)+d)肟菌酯;
a)+d)氟嘧菌酯;
a)+d)联苯吡菌胺;
a)+d)二氯异噁草酮;
a)+d)异丙菌胺;
a)+d)氟吡菌酰胺
a)+d)螺菌胺;
a)+d)氟嘧菌酯+肟菌酯;
a)+d)肟菌酯+螺菌胺;
a)+d)联苯吡菌胺+戊唑醇;
a)+d)联苯吡菌胺+氟嘧菌酯;
a)+d)联苯吡菌胺+肟菌酯;
a)+d)联苯吡菌胺+螺菌胺;
a)+d)联苯吡菌胺+氟吡菌酰胺;
a)+d)戊唑醇+螺菌胺;
a)+d)戊唑醇+氟吡菌酰胺;
a)+d)N-(5-氯-2-异丙基苄基)-N-环丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺;
a)+d)N-(5-氯-2-异丙基苄基)-N-环丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺+戊唑醇;
a)+d)N-(5-氯-2-异丙基苄基)-N-环丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺+氟吡菌酰胺;
a)+d)联苯吡菌胺+2-甲基丙酸(3S,6S,7R,8R)-8-苄基-3-[({3-[(异丁酰基氧基)甲氧基]-4-甲氧基吡啶-2-基}羰基)氨基]-6-甲基-4,9-二氧代-1,5-二氧杂环壬烷-7-基酯(lyserphenvalpyr)。
本发明的制剂中的组分d)的含量优选为1重量%至40重量%,特别优选3重量%至35重量%。
溶剂e):
所述制剂可以包含溶剂e),例如在EC、OD或SE制剂的情况下。
·芳族烃,例如石油溶剂油、石油、烷基苯和锭子油、二甲苯、甲苯或烷基萘;
·脂族/脂环族烃,例如矿物油、己烷、庚烷、辛烷、壬烷、癸烷、环戊烷、环己烷、十氢化萘或白油;
·氯化芳族或脂族烃,例如氯苯、氯乙烯或二氯甲烷、氯仿或四氯甲烷;
·醇,例如甲醇、乙醇、异丙醇、丁醇、乙二醇、丙二醇或苄醇;
·醚,例如四氢呋喃、四氢糠醇、四氢吡喃、1,4-二氧杂环己烷、二乙醚、甲基叔丁基醚、二己基醚、二辛基醚、二癸基醚、二苄基醚、二甲基异山梨醇、二苯醚、乙基苯基醚、苯基苄基醚或茴香醚;
·单酯/二酯/甘油酯,例如乙酸乙酯、丙酸丁酯、丙酸戊酯、乙酸苄酯、苯甲酸苄酯、苯甲酸丁酯、Polarclean、RPDE、乳酸甲酯、乳酸乙酯、乳酸丙酯、乳酸丁酯、乳酸2-乙基己酯、3-乙氧基丙酸乙酯(Ester EEP,DowChemical Company)、琥珀酸二甲酯、琥珀酸二乙酯、琥珀酸二丙酯、己二酸二甲酯、己二酸二乙酯、己二酸二丙酯、戊二酸二甲酯、戊二酸二乙酯、戊二酸二丙酯、双(2-乙基己基)己二酸酯、己二酸二异丙酯、2-甲基戊二酸二甲酯、马来酸二辛酯、甘油单乙酸酯、甘油二乙酸酯、甘油三乙酸酯、植物油,例如菜籽油、葵花油、大豆油、蓖麻油或玉米油;
·内酯,例如丁内酯、α-甲基-γ-丁内酯、γ-戊内酯或δ-戊内酯;
·聚环氧乙烷/环氧丙烷,例如单乙二醇、单乙二醇单甲醚、单乙二醇单乙醚、单乙二醇单丙醚、单乙二醇单丁醚、单乙二醇单戊醚、单乙二醇单己醚、单乙二醇单苯醚、单乙二醇二甲醚、单乙二醇二乙醚、单乙二醇二丙醚、单乙二醇二丁醚、单乙二醇二戊醚、单乙二醇二己醚、单乙二醇二苯醚及其较长的乙二醇同系物;单丙二醇、单丙二醇单甲醚、单丙二醇单乙醚、单丙二醇单丙醚、单丙二醇单丁醚、单丙二醇单戊醚、单丙二醇单己醚、单丙二醇单苯醚、单丙二醇二甲醚、单丙二醇二乙醚、单丙二醇二丙醚、单丙二醇二丁醚、单丙二醇二戊醚、单丙二醇二己醚、单丙二醇二苯醚及其较长的丙烯同系物;单乙二醇单甲醚乙酸酯、单乙二醇二乙酸酯及其较长的乙二醇同系物;单丙二醇单甲醚乙酸酯、单丙二醇乙酸酯及其较长的聚丙二醇同系物;
·简单和取代的胺,例如二乙胺、三乙胺、二异丙胺、二异丙基乙胺、单乙醇胺、二乙醇胺、三乙醇胺以及更高级的烷氧基化胺、苯胺或二甲基苯胺;
·酰胺/脲,例如N-甲酰基吗啉、N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N,N-二甲基苯甲酰胺、N,N-二甲基辛酰胺、N,N-二甲基癸酰胺、N,N-二甲基癸9-烯-1-酰胺、N,N-二甲基十二烷酰胺、N,N-二甲基乳酰胺、N,N-癸基甲基甲酰胺、N-甲基-2-吡咯烷酮、N-乙基-2-吡咯烷酮、N-丙基-2-吡咯烷酮、N-丁基-2-吡咯烷酮、N-戊基-2-吡咯烷酮、N-己基-2-吡咯烷酮、N-庚基-2-吡咯烷酮、N-辛基-2-吡咯烷酮、N-壬基-2-吡咯烷酮、N-癸基-2-吡咯烷酮、N-十一碳烯基-2-吡咯烷酮、N-十二烷基-2-吡咯烷酮、N-甲基-2-哌啶酮、N-甲基己内酰胺、N-辛基己内酰胺、四甲基脲、四乙基脲、1,3-二甲基-2-咪唑烷酮、1,3,4-三甲基-2-咪唑烷酮、1,3-二甲基-3,4,5,6-四氢-2(1H)-嘧啶酮、1-庚基-3-甲基-2-咪唑烷酮、1-庚基-1,3-二氢-3-甲基-2H-咪唑-2-酮;
·酮,例如丙酮、双丙酮醇、甲乙酮、2-戊酮、3-戊酮、2-己酮、3-己酮、2-庚酮、3-庚酮、4-庚酮、2-辛酮、3-辛酮、4-辛酮、甲基异丙基酮、甲基异丁基酮、甲基异戊基酮、乙基异丙基酮、乙基异丁基酮、乙基异戊基酮、丙基异丙基酮、丙基异丁基酮、丙基异戊基酮、3,3-二甲基-2-丁酮、2,4-二甲基-3-戊酮、4,4-二甲基-2-戊酮、2,6-二甲基-4-庚酮、2,2,4,4-四甲基-3-戊酮、环戊酮、环己酮、环庚酮、环辛酮、2,4,6-环庚三烯-1-酮、苯乙酮、苯丙酮、1-(4-甲基苯基)乙酮、1-(4-乙基苯基)乙酮、2-甲基-1-苯基-1-丙酮、1-(3-乙基苯基)乙酮、4-苯基-2-丁酮、1-苯基-2-丙酮、1-苯基-2-丁酮、2-苯基-3-丁酮、苯丁酮或苯戊酮。
·腈,例如乙腈、丙腈、2-甲基丙腈、丁腈、3-甲基丁腈、戊腈、4-甲基戊腈、己腈、庚腈、辛腈、壬腈、癸腈、苄腈、苯乙腈、戊二腈、2-甲基戊二腈、己二腈、庚二腈、辛二腈或壬二腈;
·缩醛,例如1,1-二甲氧基甲烷;1,1-二甲氧基乙烷;1,1'-[亚甲基双(氧基)]双乙烷;1,1-二乙氧基乙烷;1,1'-[亚甲基双(氧基)]双丙烷;2,4,6,8-四氧杂壬烷、1,1'-[亚甲基双(氧基)]双丁烷、2-甲基-1-[(2-甲基丙氧基)甲氧基]丙烷、2,4,6,8,10-五氧杂十一烷、2,5,7,10-四氧杂十一烷、1,3-二氧杂环戊烷、1,3-二氧杂环己烷或4-甲基-1,3-二氧杂环己烷;原酸酯例如1,1,1-三甲氧基甲烷、1,1,1-三甲氧基乙烷、1,1,1-三甲氧基丙烷、2-甲氧基-1,3-二氧杂环戊烷、2-甲氧基-2-甲基-1,3-二氧杂环戊烷、2-甲氧基-2-甲基-1,3-二氧杂环戊烷、2-乙氧基-1,3-二氧杂环戊烷、2-乙氧基-2-甲基-1,3-二氧杂环戊烷、2-乙基-2-甲氧基-1,3-二氧杂环戊烷、2-甲氧基-1,3-二氧杂环己烷、2-甲氧基-2-甲基-1,3-二氧杂环己烷或2-乙氧基-1,3-二氧杂环己烷;
·碳酸酯,例如碳酸二甲酯、碳酸甲乙酯、碳酸二乙酯、碳酸二丙酯、碳酸二异丙酯、碳酸二丁酯、碳酸二戊酯、碳酸二己酯、碳酸二庚酯、碳酸二辛酯、碳酸二壬酯、碳酸二癸酯、碳酸亚乙酯、4-甲基-1,3-二氧杂环戊烷-2-酮、4-(甲氧基甲基)-1,3-二氧杂环戊烷-2-酮、甘油碳酸酯、碳酸亚丁酯、4,6-二甲基-3-二氧杂环己烷-2-酮或碳酸二苄酯;
·磷酸酯,例如磷酸三甲酯、磷酸三乙酯、磷酸三丙酯、磷酸三丁酯、磷酸三异丁酯、磷酸三戊酯、磷酸三己酯、磷酸三(2-乙基己基)酯、磷酸三(2-丁氧基乙基)酯或磷酸三苯酯;
·亚砜,例如二甲基亚砜、二乙基亚砜、1,1-二氧代四氢噻吩、1,1-二氧代四氢-3-甲基噻吩或1,1-二氧代四氢-2,4-二甲基噻吩。
此外,本发明的制剂可以任选地包含液体填料e),例如植物油或矿物油、或植物油或矿物油的酯。合适的植物油e)是通常可用于农业化学品并可从植物获得的所有油。实例包括葵花油、菜籽油、橄榄油、蓖麻油、菜子油、玉米油、棉籽油、核桃油、椰子油和大豆油。可能的酯是例如棕榈酸乙基己酯、油酸乙基己酯、肉豆蔻酸乙基己酯、辛酸乙基己酯、肉豆蔻酸异丙酯、棕榈酸异丙酯、油酸甲酯、棕榈酸甲酯、油酸乙酯。优选菜籽油甲酯和棕榈酸乙基己酯。可能的矿物油是D100和白油。
表1:优选化合物e)的示例性商品名和CAS号
用于WG的载体材料f)
本发明的制剂中的填料和载体材料f)选自矿物质;碱土金属和碱金属的碳酸盐、硫酸盐和磷酸盐,例如碳酸钙;聚合碳水化合物;架状硅酸盐,例如具有低吸附性的沉淀二氧化硅,以及天然架状硅酸盐,例如高岭土。合适的填料f)的典型代表是例如(绿坡缕石)、300(珍珠岩)、HV(改性淀粉)、白垩(碳酸钙)、Tec 1(高岭土、水合硅酸铝)、OOS(滑石、硅酸镁)。对于c2),这里优选天然架状硅酸盐和碳酸钙产品例如白垩(碳酸钙)、Kaolin Tec(高岭土)和300(珍珠岩),特别优选天然架状硅酸盐例如1(高岭土、水合硅酸铝)和300(珍珠岩)。对于WG制剂,非常特别优选使用高岭土和碳酸钙。其它合适的载体材料或填料f)选自具有至少200g邻苯二甲酸二丁酯/100g载体材料的吸收能力的高吸附性载体。优选的高吸附性载体f)是二氧化硅,例如产品(高吸附性的合成沉淀二氧化硅)和热解二氧化硅(产品)。优选沉淀二氧化硅。本发明的TC中的填料f)的含量为优选0.1重量%至10重量%,特别优选0.3重量%至8重量%,且非常特别优选1重量%至7重量%。
增稠剂g)
有用的增稠剂g)包括有机增稠剂g1)和无机增稠剂g2)。
有用的有机增稠剂g1)包括有机天然或生物技术改性或有机合成的增稠剂。典型的合成增稠剂是(Croda)或或系列(Elementis)。这些通常基于丙烯酸酯。典型的有机增稠剂基于黄原胶或纤维素(例如羟乙基或羧甲基纤维素)或其组合。其它典型的代表基于木质素(例如木质素磺酸盐、NA、88或Kraftsperse 25S)。优选使用基于黄原胶的天然改性增稠剂。典型代表是例如(Solvay)和(Kelco Corp.)以及(Cargill)。
根据本发明B)的SC中的有机增稠剂g1)的含量为不超过5重量%,优选0.01重量%至1.0重量%,更优选0.01重量%至0.6重量%,甚至更优选0.05重量%至0.5重量%,且甚至更优选0.1重量%至0.3重量%。
合适的无机增稠剂d2)为例如改性的天然硅酸盐,例如化学改性的膨润土、锂蒙脱石、绿坡缕石、蒙脱石、蒙皂石(smectite)或其它硅酸盐矿物,例如(Elementis)、(Engelhard)、(Oil-Dri Corporation)或(Akzo Nobel),或Van Gel系列(R.T.Vanderbilt)。
本发明的制剂中的无机增稠剂g2)的含量为0重量%至5重量%,优选0.1重量%至3重量%,更优选0.2重量%至1.5重量%,甚至更优选0.3重量%至1.5重量%,且甚至更优选0.4重量%至1.3重量%。
其它组分h)
此外,本发明的SC或TC或WG还可以任选包含以下物质作为其它组分h):
润湿剂、pH调节剂、消泡剂、杀生物剂、崩解剂、粘附促进剂、防冻剂、防腐剂、染料或肥料,以及不同于组分c)的表面活性剂。
合适的消泡剂为基于硅酮或基于硅烷的表面活性化合物,例如产品(Goldschmidt)、产品(Wacker)以及(Kemira)、(Solvay)和产品(Blustar Silicones),优选产品(Wacker)、和产品,特别优选例如产品例如5020。
合适的防冻剂是选自脲、二醇和多元醇的那些,例如乙二醇和丙二醇、甘油,优选丙二醇或甘油。
合适的粘附促进剂可选自聚乙烯吡咯烷酮(PVP)、聚乙烯醇、PVP与甲基丙烯酸二甲基氨基乙基酯的共聚物、丁基化PVP、氯乙烯和乙酸乙烯酯的共聚物、丙烯磺酸(propenesultanic acid)和部分水解乙酸乙烯酯的共聚物的钠盐、酪蛋白酸钠、酚醛树脂、改性纤维素类型,例如(聚乙烯吡咯烷酮)、(聚乙烯醇)、改性纤维素。
合适的消泡剂可选自磷酸与低级醇的酯,C6-C10醇,硅酮表面活性剂(疏水化二氧化硅颗粒在基于液体硅酮表面活性剂的水性乳液浓缩物中的悬乳剂),例如聚二甲基硅氧烷,及其在固体载体材料上的被吸收物,例如432(硅酮表面活性剂)、磷酸丁酯、磷酸异丁酯、正辛醇、Wacker ASP15(聚二甲基硅氧烷,吸收在固体载体上)、SE(聚二甲基硅氧烷)。优选疏水化二氧化硅颗粒在基于液体硅酮表面活性剂的水性乳液浓缩物中的悬乳剂,例如消泡剂SE(聚二甲基硅氧烷),以及固体消泡剂,如Wacker ASP 15(聚二甲基硅氧烷)。
可任选地存在于本发明的制剂中的其它添加剂h)是渗透剂、润湿剂、铺展剂和/或助留剂。合适的物质是在农业化学品中通常可用于该目的的所有物质。
合适的添加剂h)是例如,
·磺基琥珀酸钠盐与具有1-10个碳原子的支链或直链醇的单酯和二酯;
表2:优选化合物h)的示例性商品名和CAS号
合适的消泡剂h是在农业化学品中通常可用于该目的的所有物质。优选硅油、硅油制剂、硬脂酸镁、次膦酸和膦酸。实例是来自Bluestar Silicones的482、来自Wacker的SC1132[二甲基硅氧烷和-硅酮,CAS号63148-62-9],来自Momentive的SAG 1538或SAG 1572[二甲基硅氧烷和-硅酮,CAS号63148-62-9]或PL 80。
可能的防腐剂h是在农业化学品中通常可用于该目的的所有物质。合适的防腐剂是例如包含5-氯-2-甲基-4-异噻唑啉-3-酮[CIT;CAS号26172-55-4]、2-甲基-4-异噻唑啉-3-酮[MIT,CAS号2682-20-4]或1,2-苯并异噻唑-3(2H)-酮[BIT,CAS号2634-33-5]的制剂。实例包括D7(Lanxess),CG/ICP(Rohm&Haas),SPX(Thor GmbH)和GXL(Arch Chemicals)。
合适的抗氧化剂h是在农业化学品中通常可用于该目的的所有物质。优选丁基羟基甲苯[3,5-二叔丁基-4-羟基甲苯,CAS号128-37-0]和柠檬酸。
可能的着色剂h是在农业化学品中通常可用于该目的的所有物质。实例包括二氧化钛、炭黑、氧化锌、蓝色颜料、红色颜料和永固红FGR。
合适的惰性填料h)是在农业化学品中通常可用于该目的且不用作增稠剂的所有物质。优选无机颗粒例如碳酸盐、硅酸盐和氧化物,以及有机物质例如脲-甲醛缩合物。实例包括高岭土、金红石、二氧化硅(“细分的二氧化硅”)、硅胶以及天然和合成的硅酸盐以及滑石。
本发明还提供基于上述组合物的水分散性工业浓缩物(TC),其包含-一种或多种阴离子型乳化剂c2,
-一种或多种非离子型乳化剂c1),
-至少一种或多于一种载体材料f。
本发明同样提供悬浮浓缩物(SC),其包含:
-一种或多种阴离子型乳化剂c2,
-一种或多种非离子型乳化剂c1,
-至少一种或多于一种增稠剂g)。
本发明同样提供EC,其包含:
-一种或多种非离子型乳化剂c1,
-至少一种溶剂e)。
本发明同样提供EC,其包含:
-一种或多种非离子型乳化剂c1,
-至少一种其它农业化学活性成分、优选杀真菌剂。
本发明同样提供OD,其包含:
-一种或多种非离子型乳化剂c1,
-一种或多种阴离子型乳化剂c2,
-至少一种溶剂e),
-至少一种增稠剂g)。
施用
可以使用的施用形式的实例包括本领域技术人员通常使用的所有已知方法:喷洒,浸渍,雾化和用于整个植株或部分(种子、根、匍匐枝、茎、干、叶)在地下或地上的直接处理的一些特定方法,例如在树的情况下的树干注射或在多年生植物的情况下茎绷带,以及一些特定的间接施用方法。
用于防治有害生物体的多种不同制剂类型的作物保护组合物的各自基于面积和/或基于对象的施用率差异很大。通常,本领域技术人员已知的通常用于相应使用领域的施用介质以用于该目的的常规量使用,例如从在标准喷洒方法的情况下每公顷数百升水、经由在“超低体积”飞机施用的情况下每公顷几升油、直至在注射方法的情况下几毫升的生理溶液。因此,本发明作物保护组合物在特定施用介质中的浓度在宽范围内变化,并且取决于各自的使用领域。通常,使用本领域技术人员已知通常用于各自使用领域的浓度。优选的浓度为0.01重量%至99重量%,更优选0.1重量%至90重量%。
本发明的农业化学制剂可以例如以通常用于液体制剂的制剂形式原样或在用水预先稀释后使用,即例如作为乳液、悬浮液或溶液。通过常规方法进行施用,即例如通过喷洒、倾倒或注射。
取决于除丙硫菌唑以外可能存在的活性成分的性质,本发明的制剂可用于防治大量的有害物,并且既可用于处理植物作物,也可用于处理无生命物质和用于家庭中。
“有害物(pest)”或“有害生物体”在本文中理解为意指可以用有机作物保护活性成分,即作物保护剂,尤其是杀真菌剂和杀真菌剂与其它作物保护剂的混合物,来防治或保持在防治下的所有种类的有害物。因此,术语“有害物”包括对植物有害的生物体,尤其是有害真菌及其孢子,以及有害昆虫(insect)、蛛形纲动物、线虫和有害植物。术语“防治”包括治疗性处理,即用本发明的制剂处理受侵染的植物,以及保护性处理,即处理植物以保护其免于有害物侵染。
因此,本发明还涉及本文中所述的制剂用于防治有害物,尤其是植物有害物的用途,以及防治有害生物体,尤其是对植物有害的生物体的方法,其包括使有害生物体、其生境、其宿主,例如植物和种子以及它们在其中生长或可能生长的土壤、区域和环境以及待保护免于被对植物有害的生物体攻击或侵染的材料、植物、种子、土壤、表面或空间与有效量的本发明的制剂接触。
本发明的另一方面涉及本文描述的制剂用于保护植物,包括种子,尤其是有用植物免受有害生物体,尤其是有害真菌侵染的用途。本发明因此还涉及所述制剂用于防治对植物有害的生物体,例如有害真菌、昆虫、蛛形纲动物、线虫和有害植物,尤其是用于防治有害真菌的用途。
本发明的制剂可以以本身已知的用于防治植物病原性真菌的方式用于作物保护中,特别是作为叶用杀真菌剂、拌种杀真菌剂和土壤杀真菌剂。
可以用本发明的制剂处理的植物包括下述:棉花、亚麻、葡萄藤、水果树、蔬菜,例如蔷薇科(Rosaceae sp.)(例如梨果,例如苹果和梨,以及核果例如杏、樱桃、扁桃和桃,以及浆果例如草莓)、茶藨子属(Ribesioidae sp.)、胡桃科(Juglandaceae sp.)、桦木科(Betulaceae sp.)、漆树科(Anacardiaceae sp.)、壳斗科(Fagaceae sp.)、桑科(Moraceaesp.)、木犀科(Oleaceae sp.)、猕猴桃科(Actinidaceae sp.)、樟科(Lauraceae sp.)、芭蕉科(Musaceae sp.)(例如香蕉树和种植园)、茜草科(Rubiaceae sp.)(例如咖啡)、山茶科(Theaceae sp.)、梧桐科(Sterculiceae sp.)、芸香科(Rutaceae sp.)(例如柠檬、橙和葡萄柚);茄科(Solanaceae sp.)(例如番茄)、百合科(Liliaceae sp.)、菊科(Asteraceaesp.)(例如莴苣)、伞形科(Umbelliferae sp.)、十字花科(Cruciferae sp.)、藜科(Chenopodiaceae sp.)、葫芦科(Cucurbitaceae sp.)(例如黄瓜)、葱科(Alliaceae sp.)(例如韭菜、洋葱)、蝶形花科(Papilionaceae sp.)(例如豌豆);主要有用植物,例如禾本科(Gramineae sp.)(例如玉米、草皮(turf),谷类例如小麦、黑麦、稻、大麦、燕麦、黍和黑小麦)、菊科(Asteraceae sp.)(例如向日葵)、十字花科(Brassicaceae sp.)(例如白球甘蓝、红球甘蓝、茎椰菜、花椰菜、抱子甘蓝、小白菜、球茎甘蓝、萝卜以及油菜、芥菜、辣根和水芹)、豆科(Fabacae sp.)(例如菜豆、花生)、蝶形花科(Papilionaceae sp.)(例如大豆)、茄科(Solanaceae sp.)(例如土豆)、藜科(Chenopodiaceae sp.)(例如糖用甜菜、饲料甜菜、唐莴苣、红甜菜);甘蔗、罂粟、橄榄、椰子、可可、烟草以及在公园和森林中的有用植物和观赏植物;以及这些植物的各自的基因修饰品种,以及这些植物的种子。
优选使用本发明的制剂用于处理小麦、大麦、黑麦、大豆、洋葱、玉米和花生。
更特别地,原则上可以使用本发明的丙硫菌唑制剂来防治也可用已知的丙硫菌唑制剂防治的所有有害真菌病害。根据每种情况下存在的特定混合配对物,所述植物病害为例如以下植物病害:
蔬菜、油菜、甜菜、大豆、谷类、棉花、水果树和稻上的链格孢属(Alternariaspecies)(例如土豆和其它植物上的早疫链格孢(A.solani)或链格孢(A.alternata)),甜菜和蔬菜上的丝囊霉属(Aphanomyces species),棉花和稻上的壳二孢属(Ascochytasp.),玉米、谷类、稻和草皮上的平脐蠕孢属(Bipolaris)和内脐蠕孢属(Drechsleraspecies)(例如大麦上的大麦网斑内脐蠕孢(teres)、小麦上的D.tritci-repentis),谷类上的小麦白粉菌(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),棉花上的蒂腐菌属(Botryodiplodia sp.),莴苣上的莴苣盘梗霉(Bremia lactucae),玉米、大豆、稻和甜菜上的尾孢属(Cerospora species)(例如甜菜上的甜菜生尾孢(C.beticula)),玉米、谷类、稻上的旋孢腔菌属(Cochliobolusspecies)(例如谷类上的禾旋孢腔菌(Cochliobolus sativus),稻上的宫部旋孢腔菌(Cochliobolus miyabeanus)),大豆、棉花和其它植物上的棒孢菌属(Corynespora sp.),大豆、棉花和其它植物上的剌盘孢属(Colletotrichum species)(例如各种植物上的尖孢炭疽菌(C.acutatum)),谷类和稻上的弯孢属(Curvularia sp.),谷类和稻上的色二孢属(Diplodia sp.),玉米上的突脐蠕孢属(Exserohilum species),黄瓜物种上的二孢白粉菌(Erysiphe cichoracearum)和单丝壳白粉菌(Sphaerotheca fuliginea),各种植物上的镰孢霉属(Fusarium)和轮生菌属(Verticillium)(例如茄黄萎病菌(V.dahliae)(例如小麦上的禾本科镰孢(F.graminearum)),谷类上的禾顶囊壳(Gaeumanomyces graminis),谷类和稻上的赤霉属(Gibberella species)(例如稻上的藤仓赤霉(Gibberella fujikuroi)),稻上的谷物染色复合物(Grainstaining complex),玉米和稻上的长蠕孢属(Helminthosporium species)(例如H.graminicola),大豆和棉花上的壳球孢属(Macrophomina sp.),叶枯菌属(Michrodochium sp.)(例如谷类上的雪霉叶枯菌(M.nivale)),谷类、香蕉和花生上的球腔菌属(Mycosphaerella species)(小麦上的禾生球腔菌(M.graminicola)、香蕉上的斐济球腔菌(M.fijiesis)),大豆上的褐柱丝霉属(Phaeoisaripsis sp.),层锈菌(Phakopsara sp.)(例如大豆上的豆薯层锈菌(P.pachyrhizi)和山马蟥层锈菌(P.meibomiae)),大豆上的茎点霉属(Phoma sp.),大豆、向日葵和葡萄藤上的拟茎点霉属(Phomopsis species)(葡萄藤上的葡萄黑腐病菌(P.viticola)、向日葵上的褐色茎腐病(P.helianthii)),土豆和番茄上的致病疫霉(Phytophthora infestans),葡萄藤上的葡萄生单轴霉(Plasmopara viticola),大豆和棉花上的青霉属(Penecilium sp.),苹果上的苹果白粉病菌(Podosphaera leucotricha),谷类上的小麦基腐病菌(Pseudocercosporella herpotrichoides),啤酒花和黄瓜物种上的假霜霉属(Pseudoperonospora species)(例如黄瓜上的古巴假霜霉(P.cubenis)),谷类、玉米和芦笋上的柄锈菌属(Puccinia species)(小麦上的小麦柄锈菌(P.triticina)和条形柄锈病(P.striformis),芦笋上的天门冬属柄锈菌(P.asparagi)),谷类上的核腔菌属(Pyrenophora species),稻上的稻瘟病菌(Pyricularia oryzae)、笹木伏革菌(Corticiumsasakii)、稻帚枝霉(Sarocladium oryzae)、S.attenuatum、稻叶黑粉菌(Entylomaoryzae),草皮和谷类上的稻梨孢菌(Pyricularia grisea),草皮、稻、玉米、棉花、油菜、向日葵、甜菜、蔬菜和其它植物上的腐霉属(Pythium sp.),棉花、稻、土豆、草皮、玉米、油菜、土豆、甜菜、蔬菜和其它植物上的丝核菌属(Rhizoctonia species)(例如立枯丝核菌(R.solani)),稻和谷类上的喙孢霉属(Rynchosporium sp.)(例如黑麦喙孢(R.secalis)),油菜、向日葵和其它植物上的核盘菌属(Sclerotinia species)(例如核盘菌(S.sclerotiorum)),小麦上的小麦壳针孢(Septoria tritici)和颖枯壳多孢(Stagonospora nodorum),葡萄藤上的葡萄钩丝壳(Erysiphe(同义词Uncinulanecator)),玉米和草皮上的大斑病菌属(Setospaeria species),玉米上的丝轴黑粉菌(Sphacelotheca reilinia),大豆和棉花上的根串珠霉属(Thievaliopsis species),谷类上的腥黑粉菌属(Tilletia species),谷类、玉米和甜菜上的黑粉菌属(Ustilagospecies),以及苹果和梨上的黑星菌属(Venturia species)(黑星病)(例如苹果上的苹果黑星病(V.Inaequalis))。
本发明的制剂可以未稀释形式或用水稀释施用。通常,基于一份制剂计,用至少一份水、优选用10份水且更优选用至少100份水,例如用1至10000份、优选10至5000份且更优选用50至24000份水将其稀释。
本发明同样提供可通过将水与本发明的液体制剂混合而获得的乳液。水与乳液浓缩物的混合比可以为1000:1至1:1,优选400:1至10:1。
通过将本发明的乳液浓缩物倒入水中来实现稀释。为了快速混合浓缩物与水,通常使用搅动,例如搅拌。然而,搅动通常是不必要的。虽然用于稀释操作的温度不是关键因素,但稀释通常在0℃至50℃的温度下进行,特别是在10℃至30℃下或在环境温度下进行。
用于稀释的水通常是自来水。然而,水可能已经含有用于作物保护中的水溶性或细分散的化合物,例如营养物、肥料或农药。
可以以预混物的形式或者——如果合适——直至在使用前不久(桶混)将各种种类的油、润湿剂、佐剂、肥料或微量营养物和其它农药(例如除草剂、杀虫剂、杀真菌剂、生长调节剂、安全剂)添加至本发明的乳液中。这些组合物可以以1:100至100:1、优选1:10至10:1的重量比添加至本发明的制剂中。
使用者通常会从预计量仪器、背负式喷洒器、喷洒罐、喷洒飞机或灌溉系统中施用本发明的制剂。通常将本发明的制剂用水、缓冲剂和/或其它助剂稀释至所需的施用浓度,这提供了本发明的即用型喷洒液体或农业化学组合物。通常,每公顷农业有用面积使用20至2000升,优选50至400升的即用型喷洒液。
没有制剂助剂的纯活性成分的所需施用率取决于有害物侵染的强度、植物的发育阶段、使用地点的气候条件和施用方法。通常,施用率为每公顷0.001至3kg,优选0.005至2kg,更优选0.01至1kg且最优选50至500g活性成分,这里的活性成分意指丙硫菌唑加上可能的其它活性成分。
本发明的通常稀释的制剂主要通过喷洒,尤其是对叶的喷洒来施用。可以通过本领域技术人员已知的喷洒技术进行施用,例如通过使用水作为载体,且喷洒液的量为每公顷约50至1000升,例如每公顷100至00升。
新的含有丙硫菌唑的制剂在植物处理方面具有有利的特性;更特别地,它们的特征在于良好的使用特性、高稳定性和高杀真菌活性。
本发明通过实施例更详细地说明,但不限于此。
实施例
使用的原料:
以下实施例中使用的术语具有以下含义:
丙硫菌唑 PTZ(Bayer AG)
Atlox Metasperse 500 Croda,丙烯酸酯基共聚物
柠檬酸 Sigma-Aldrich
维生素C Sigma-Aldrich,抗坏血酸
维生素E Sigma-Aldrich,α-生育酚
Pluronic PE 10500 环氧丙烷/环氧乙烷(PO-EO)嵌段聚合物(BASF)
Glycerol 防冻剂
水性悬浮浓缩物(SC)的一般制备:
首先,在室温下首先加入水。伴随搅拌添加活性成分和其它组分(没有特别的顺序)。将混合物在胶体磨中预粉碎,随后使用例如珠磨机进行湿磨。最后,添加有机增稠剂。
乳液浓缩液(EC)的一般制备
首先加入有机溶剂。然后伴随搅拌添加所有其它组分(没有特别的顺序)。继续搅拌直至形成澄清溶液。
制剂中的2-(1-氯环丙基)-1-(2-氯苯基)-3-(1H-1,2,4-三唑-1-基)丙-2-醇(化
合物III)的测定
在反相柱上使用等度洗脱剂将2-(1-氯环丙基)-1-(2-氯苯基)-3-(1H-1,2,4-三唑-1-基)丙-2-醇与制剂成分分离。在MS/MS检测后,通过使用外标将峰面积与参考对象的峰面积进行比较来进行定量评估。
在每种情况下,除非另有说明,否则将样品暴露于光并储存4周。
实施例1:丙硫菌唑乳液浓缩物制剂的配方(在黑暗中储存)
快速储存结果:
如实施例1e中所示,在10%维生素E的浓度下,在制剂中发生不希望的作用(结晶、沉降),然而即使在制剂中1%的维生素E含量下,也可以测量到对化合物III的减少的积极作用。
将实施例1f在室温下在容器——仅填充最高达约10%——中、在透明的实验室窗口处储存4周。即使在这些非典型的条件下(暴露于空气和光),化合物III的含量也保持在21ppm,因此显著低于62.5ppm的允许的EU阈值。
实施例2:丙硫菌唑悬浮浓缩剂的配方
快速储存结果:
在制剂中维生素C的含量最高达3%时,制剂的性质没有不利的变化。即使在0.1%维生素C的含量下,也可以在减少化合物III方面取得积极效果。
实施例3:丙硫菌唑油分散体(具有维生素E)的配方
快速储存结果:
即使少量的维生素E也能在光下稳定丙硫菌唑,并减少OD制剂中化合物III的形成。
实施例4:
UV阻断剂的作用
表条目1:
将0.4g丙硫菌唑和1.6g N,N-二甲基癸酰胺合并在20mL小瓶中。
表条目2:
如表条目1,添加60mg奥克立林(octocrylene)。
表条目3:
将0.4g丙硫菌唑、1.6g乙腈和0.78g丙酮合并在20ml小瓶中。
使用LED灯(波长450nm,47mW/cm2)伴随搅拌(磁力搅拌器)将所有反应混合物在光反应器中照射24小时。然后取样并通过HPLC色谱(柱:Agilent Zorbax Eclipse Plus C18,50×4.6mm,1.8μm,流动相:乙腈/0.1重量%的磷酸水溶液,梯度为2ml/min,温度:45℃,外标)测定化合物III的相应含量。
即使在纯DAA中并且与UV阻断剂结合,在照射时也形成显著比例的脱硫物,如在纯溶剂(乙腈/丙酮)中一样。
实施例5:
5重量%添加剂对N,N-二甲基癸酰胺中丙硫菌唑的影响
将0.4g丙硫菌唑、1.5g N,N-二甲基癸酰胺和0.1g相应的稳定剂合并在20mL小瓶中。使用LED灯(波长350nm,19mW/cm2)伴随搅拌(磁力搅拌器)将反应混合物在光反应器中照射24小时。然后取样并通过HPLC色谱(柱:Agilent Zorbax Eclipse Plus C18,50×4.6mm,1.8μm,流动相:乙腈/0.1重量%的磷酸水溶液,梯度为2ml/min,温度:45℃,外标)测定化合物III的相应含量。
从上表可以看出,并非所有抗氧化剂均导致丙硫菌唑在减少脱硫物形成方面的稳定化。相反,它们中的一些甚至似乎具有负面作用(增加的脱硫物形成)。
实施例6:
20%的丙硫菌唑与DAA:
将一定量的(+/-)-α-生育酚(参见下表)加入到透明的50mL玻璃瓶中,然后使用20重量%的丙硫菌唑的N,N-二甲基癸酰胺溶液将内容物补足至5g的总重量。摇动瓶子,并在室外试验中暴露于直射阳光2周。然后取样并通过HPLC色谱(柱:Agilent Zorbax EclipsePlus C18,50×4.6mm,1.8μm,流动相:乙腈/0.1重量%的磷酸水溶液,梯度为2ml/min,温度:45℃,外标)测定化合物III的相应含量。
丙硫菌唑的EC250制剂:
将一定量的(+/-)-α-生育酚(参见下表)加入到透明的50mL玻璃瓶中,然后使用丙硫菌唑的EC250制剂将内容物补足至5g的总重量。摇动瓶子,并在室外试验中暴露于直射阳光2周。然后取样并通过HPLC色谱(柱:Agilent Zorbax Eclipse Plus C18,50×4.6mm,1.8μm,流动相:乙腈/0.1重量%的磷酸水溶液,梯度为2ml/min,温度:45℃,外标)测定化合物III的相应含量。
如上述实验所示,即使在EC250制剂和20重量%的丙硫菌唑在DAA中的溶液中均加入基于组合物的总重量计1重量%的(+/-)-α-生育酚时,在室外试验中化合物III的形成也显著减少,当浓度增加至3重量%的生育酚时,效果甚至更明显。
实施例7:
将2g丙硫菌唑的SC325(Fox325)制剂和SC450制剂(XPRO SC450)与下表中所述量的维生素C合并在20mL小瓶中。使用LED灯(波长450nm,47mW/cm2)伴随搅拌(磁力搅拌器)将反应混合物在光反应器中照射24小时。然后取样并通过HPLC色谱(柱:Agilent ZorbaxEclipse Plus C18,50×4.6mm,1.8μm,流动相:乙腈/0.1重量%的磷酸水溶液,梯度为2ml/min,温度:45℃,外标)测定化合物III的相应含量。
如上述实验所示,即使仅添加0.1重量%,维生素C也非常有效地保护丙硫菌唑的SC制剂。当维生素C含量最高达3重量%时,效果随着维生素C含量的增加而增加。
实施例8:
将2g表中所述的EC制剂(分散剂:N,N-二甲基癸酰胺)与1或3重量%的(+/-)α-生 育酚合并在20mL小瓶中。使用LED灯(波长365nm,19mW/cm2)伴随搅拌(磁力搅拌器)将反应混合物在光反应器中照射24小时。然后取样并通过HPLC色谱(柱:Agilent Zorbax EclipsePlus C18,50×4.6mm,1.8μm,流动相:乙腈/0.1重量%的磷酸水溶液,梯度为2ml/min,温度:45℃,外标)测定化合物III的相应含量。
如上述实验所示,通过加入(+/-)α-生育酚,在含有丙硫菌唑的市售制剂中也可以显著减少脱硫物的形成。
Claims (21)
1.制剂,其包含
a)具有硫酮基团的活性成分,和
b)至少一种选自以下物质的抗氧化剂:抗坏血酸、生育三烯酚、生育酚(例如(+)-δ-生育酚、(+/-)-α-生育酚)、生育酚的混合物、硫代乳酸、BHT、丁子香酚、咖啡酸(3,4-二羟基肉桂酸)、巯基丙酸和D,L-硫苏糖醇。
2.根据权利要求1所述的制剂,其特征在于所述抗氧化剂选自抗坏血酸、生育三烯酚、生育酚及其混合物。
3.根据权利要求1所述的制剂,其特征在于所述制剂为具有抗坏血酸作为抗氧化剂的水性制剂。
4.根据权利要求1所述的制剂,其特征在于所述制剂为基于有机溶剂的制剂,并且所述抗氧化剂选自生育三烯酚和生育酚及其混合物。
5.根据前述权利要求中任一项所述的制剂,其特征在于所述活性成分a)选自丙硫菌唑和4-((6-(2-(2,4-二氟苯基)-1,1-二氟-2-羟基-3-(5-巯基-1H-1,2,4-三唑-l-基)丙基)吡啶-3-基)氧基)苯甲腈。
6.根据前述权利要求中任一项所述的制剂,其特征在于所述活性成分a)为丙硫菌唑。
7.根据前述权利要求中任一项所述的制剂,其特征在于组分a)的含量为1重量%至50重量%。
8.根据前述权利要求中任一项所述的制剂,其特征在于组分b)的含量为0.01重量%至15.00重量%。
9.根据前述权利要求中任一项所述的制剂,其特征在于其为水性SC制剂,并且组分b)的含量为0.01重量%至10.00重量%。
10.根据前述权利要求中任一项所述的制剂,其特征在于其为非水性EC或OD制剂,并且EC制剂中组分b)的含量优选为0.05重量%至15.00重量%,并且OD制剂中组分b)的含量优选为0.1重量%至5.00重量%。
11.根据前述权利要求中任一项所述的制剂,其特征在于该制剂包含以下组分中的至少一种:
c)c1:非离子型分散剂/乳化剂,
c2:离子型分散剂/乳化剂,
d)不同于a)的其它农业化学活性成分,
e)溶剂,包括OD载体,
f)载体(WG,以及用于SC/TC/WG的Aerosil),
g)g1:有机增稠剂,
g2:无机增稠剂,
h)其它添加剂和助剂。
12.根据权利要求11所述的制剂,其特征在于其包含非离子型乳化剂(c1)和/或阴离子型乳化剂(c2)。
13.根据权利要求11所述的制剂,其特征在于农业化学活性成分d)为一种或多种杀虫活性成分或杀真菌活性成分。
14.根据权利要求11所述的制剂,其特征在于所述其它农业化学活性成分d)为联苯吡菌胺。
15.根据权利要求11所述的制剂,其特征在于其含有不超过5重量%的水。
16.通过混合组分a)和b)以及任选的其它添加剂来制备根据前述权利要求中任一项所述的制剂的方法。
17.防治有害生物体的方法,其包括使有害生物体、其生境、其宿主,例如植物和种子以及它们在其中生长或可能生长的土壤、区域和环境以及待保护免于被对植物有害的生物体攻击或侵染的材料、植物、种子、土壤、表面或空间与有效量的根据权利要求1所述的制剂接触。
18.根据前述权利要求中任一项所述的制剂用于保护植物,包括种子,尤其是有用植物免受有害生物体侵染的用途。
19.根据前述权利要求中任一项所述的制剂用于防治对植物有害的生物体,例如植物病原性有害真菌、昆虫、蛛形纲动物、线虫和有害植物的用途。
20.根据权利要求18或19所述的用途,其特征在于所述有害生物体为植物病原性有害真菌。
21.乳液,其可通过将水与根据权利要求1所述的制剂混合而获得,其中水与乳液浓缩物的混合比可以为1000:1至1:1。
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