CN101437806B - 1,2-苯并异噻唑衍生物及农业或园艺用植物病害防除剂 - Google Patents
1,2-苯并异噻唑衍生物及农业或园艺用植物病害防除剂 Download PDFInfo
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Abstract
本发明提供一种1,2-苯并异噻唑衍生物或其盐、及含有该衍生物或其盐作为有效成分的农业或园艺用植物病害防除剂,其中,1,2-苯并异噻唑衍生物或其盐对作物不产生药害,且对稻瘟病、小麦颖枯病、黄瓜霜霉病、黄瓜炭疽病等具有显著的防除效果。本发明的1,2-苯并异噻唑衍生物或其盐的特征在于,由下述通式[I]表示。式中,R1表示氢原子或卤原子,R2表示甲基或卤原子。
Description
技术领域
本发明涉及1,2-苯并异噻唑衍生物或其盐、以及以该衍生物或其盐为有效成分的农业或园艺用植物病害防除剂。
背景技术
在农业或园艺作物的栽培中,针对作物的病害,正在使用多种病害防除剂,从其防除效果不充分、具有耐药性的病原菌的出现导致的使用受限、及对植物体产生药害及污染、或者对人畜鱼类的毒性及对环境的影响的观点出发,目前的病害防除剂中能令人满意的病害防除剂很少。因此,强烈要求出现上述的缺点少、使用安全的病害防除剂。
非专利文献1中记载了和本发明化合物类似的3-(甲氧基吡啶)-1,2-苯并异噻唑化合物,但没有记载在1,2-苯并异噻唑环的3位上通过氧原子键合有被取代的异噻唑-5-基甲氧基的化合物,且没有关于农业或园艺用植物病害防除剂的记载。
专利文献1中,作为具体例,记载了和本发明化合物类似的3-(吡啶-4-基甲氧基)-1,2-苯并异噻唑衍生物,但没有记载在1,2-苯并异噻唑环的3位上通过氧原子键合有被取代的异噻唑-5-基甲氧基的化合物。另外,该文献中虽然记载了以该1,2-苯并异噻唑衍生物作为植物病害防除剂,但其病害防除效果不一定令人满意。
非专利文献1:Journal of the Korean Chemical Society、第41卷、666页(1997年)
专利文献1:特开昭56-133287号公报
发明内容
发明要解决的课题
本发明的课题在于解决目前的植物病害防除剂存在的如上所述的问题点,进一步提供防除效果、残效性等优良的植物病害防除剂。
解决课题的方法
本发明人等为了达成上述目的,合成了很多到目前为止其植物病害防除活性尚未知晓的1,2-苯并异噻唑衍生物,并对其植物病害防除活性和有用性进行了深入的研究。结果发现,通过对植物预先施用本发明的1,2-苯并异噻唑衍生物(以下称为本发明化合物)或其盐,可以长时间地防除植物病害,且不会对植物产生药害,显示出显著的植物病害防除效果,由此完成了本发明。
即,本发明涉及下述(1)~(4)项内容。
(1)1,2-苯并异噻唑衍生物或其盐,其特征在于,由通式[I]表示。
[化1]
[式中,R1表示氢原子或卤原子,R2表示甲基或卤原子。]
(2)上述(1)所述的1,2-苯并异噻唑衍生物或其盐,其中,R1为氢原子、氯原子或溴原子,R2为甲基、氯原子或溴原子。
(3)上述(1)所述的1,2-苯并异噻唑衍生物或其盐,其中,R1为氯原子或溴原子,R2为氯原子或溴原子。
(4)一种农业或园艺用植物病害防除剂,其特征在于,含有上述(1)~(3)中所述的1,2-苯并异噻唑衍生物或其盐作为有效成分。
发明效果
本发明的农业或园艺用植物病害防除剂不仅对作物不产生药害,而且对稻瘟病、小麦颖枯病、黄瓜霜霉病、黄瓜炭疽病等病害具有很高的防除效果,因此可用作农业或园艺用植物病害防除剂。
具体实施方式
以下将通式[I]表示的本发明化合物的具体例示于表1。但本发明化合物并不限定于这些化合物。化合物的编号参照如下记载。
[表1]
本发明化合物的代表性制造方法如下所示,但本发明化合物的制造方法并不限定于该方法。
[化2]
(式中,X表示氯原子、溴原子等卤原子,R1和R2与上述定义相同。)
(工序1)
通式[I]表示的本发明化合物可通过将通式[II]表示的3-卤代-1,2-苯并异噻唑-1,1-二氧化物与通式[III]表示的化合物在碱存在或碱不存在下、在溶剂中或不在溶剂中进行反应来制造(以下,例如“通式[III]表示的化合物”和“化合物[III]”的意思相同。)。
另外,本工序中使用的化合物[II]可以由糖精根据Synlett,1997年、No.12、1355页所记载的方法制造。
化合物[III]的使用量,相对于1mol化合物[II]为0.5~10mol即可,优选为0.8~1.2mol。
作为本工序中可使用的碱,例如可举出:碳酸钠、碳酸钾等金属碳酸盐类;碳酸氢钠、碳酸氢钾等金属碳酸氢盐类;乙酸钠、乙酸钾等羧酸盐类;甲醇钠、乙醇钠、叔丁醇钾等金属醇盐;氢氧化钠、氢氧化钾、氢氧化钙等金属氢氧化物;氢化钠、氢化钾、氢化钙等金属氢化物;三乙胺、N,N-二异丙基乙胺、吡啶、1,8-二氮杂双环[5.4.0]十一碳-7-烯(DBU)等有机碱等。
碱的使用量,相对1mol化合物[III]为0~10mol的范围即可,优选为0~1.2mol。
作为可用于本反应的溶剂,只要不阻碍本反应的进行即可,例如可以使用:二乙醚、四氢呋喃(THF)、二噁烷、单甘醇二甲醚、二甘醇二甲醚等醚类;二氯甲烷、氯仿、四氯化碳、二氯乙烷等卤代烃类;苯、氯苯、硝基苯、甲苯、二甲苯等芳香烃类;N,N-二甲基甲酰胺(DMF)、N,N-二甲基乙酰胺等酰胺类;1,3-二甲基-2-咪唑烷酮等尿素类;二甲亚砜等硫化合物类;乙腈等腈类等,也可以使用它们的混合溶剂。
反应温度为-20℃~所用溶剂的沸点范围即可,优选为0℃~50℃的范围。
反应时间根据反应温度、反应底物、反应量等的不同而不同,通常为30分钟~48小时。
作为反应目的物的、通式[I]表示的本发明化合物,可以在反应结束后采用常规方法从反应体系中取出。所得目的物根据需要可以通过柱色谱法、重结晶等操作进行精制。
另一方面,本工序中使用的化合物[III]还可以通过以下制造方法制造。
[化3]
(工序2)
通式[V]表示的化合物可以通过使通式[IV]表示的化合物和卤化试剂在溶剂中或不在溶剂中进行反应来制造。
作为可用于本工序的卤化试剂,例如有:草酰氯或亚硫酰氯等酰卤化物等。此外,根据需要可以以催化剂的量添加N,N-二甲基甲酰胺等酰胺类。
卤化试剂的使用量,相对1mol通式[IV]表示的化合物为1~100mol的范围即可,优选为1~5mol。
作为可用于本反应的溶剂,只要不阻碍本反应的进行即可,例如可以使用:二乙醚、四氢呋喃、二噁烷、单甘醇二甲醚、二甘醇二甲醚等醚类;二氯甲烷、氯仿、四氯化碳、二氯乙烷等卤代烃类;苯、氯苯、硝基苯、甲苯、二甲苯等芳香烃类;乙腈等腈类等,还可以使用它们的混合溶剂。
此外,溶剂的使用量,相对1mol通式[IV]表示的化合物为0~100L,优选为0~2.0L。
反应温度为-20℃~所用惰性溶剂的沸点范围即可,优选为0℃~100℃的范围。
反应时间根据反应温度、反应底物、反应量等的不同而不同,通常为30分钟~10小时。
通式[V]表示的化合物在反应结束后可通过常规方法从反应体系中取出,根据需要可通过柱色谱法、重结晶等操作进行精制。
(工序3)
通式[III]表示的化合物可以通过使通式[V]表示的化合物和还原剂在溶剂中或不在溶剂中进行反应来制造。
作为可用于本工序的还原剂,例如有:硼氢化钠等硼氢化物等。
还原剂的使用量,相对1mol通式[V]表示的化合物为1~100mol的范围即可,优选为1~5mol。
作为可用于本反应的溶剂,只要不阻碍本反应进行即可,可以使用例如:二乙醚、四氢呋喃(THF)、二噁烷、单甘醇二甲醚、二甘醇二甲醚等醚类;甲醇、乙醇、丙醇、异丙醇、丁醇、叔丁醇等醇类;二氯甲烷、氯仿、四氯化碳、二氯乙烷等卤代烃类;苯、氯苯、硝基苯、甲苯、二甲苯等芳香烃类;N,N-二甲基甲酰胺、N,N-二甲基乙酰胺等酰胺类;1,3-二甲基-2-咪唑烷酮等尿素类;二甲亚砜等硫化物类;乙腈等腈类;水等,还可以使用它们的混合溶剂。
此外,溶剂的使用量,相对1mol通式[V]表示的化合物为0~100L,优选为0.1~2.0L。
反应温度为-20℃~所用惰性溶剂的沸点范围即可,优选为0℃~100℃的范围。
反应时间根据反应温度、反应底物、反应量等的不同而不同,通常为10分钟~10小时。
通式[III]表示的化合物在反应结束后可以利用常规方法从反应体系中取出,根据需要可以通过柱色谱法、重结晶等操作进行精制。
本发明的农业或园艺用植物病害防除剂含有通式[I]表示的苯并异噻唑衍生物或其盐作为有效成分。
将本发明化合物作为农业或园艺用植物病害防除剂使用时,可以使用本发明化合物本身,也可以在其中配合作为农药辅助剂的一般用于制剂化的载体、表面活性剂及其它辅助剂,从而将本发明化合物制成乳剂、混悬剂、粉剂、颗粒剂、片剂、水合剂、水溶剂、液体制剂、流化剂、水分散剂、喷雾剂、糊剂、油剂、乳浊剂、发烟剂等各种形态。对于它们的配合比例,通常,相对于0.1~90重量%的有效成分,配合10~99.9重量%的农药辅助剂。
制作制剂时可使用的载体,分为固体载体和液体载体。作为固体载体,例如有:淀粉、活性碳、大豆粉、小麦粉、木质粉、鱼粉、奶粉等动植物性粉末;滑石粉、高岭土、皂土、碳酸钙、沸石、硅藻土、白炭黑、粘土、氧化铝、蛭石、硅砂、硫酸铵、尿素等无机粉末等。作为液体载体,例如有:水;异丙醇、甘醇等醇类;环已酮、丁酮、异佛尔酮等酮类;二噁烷、四氢呋喃等醚类;煤油、汽油等脂肪烃类;二甲苯、三甲苯、四甲苯、甲基萘、溶剂石脑油等芳香烃类;氯苯等卤代烃类;二甲基乙酰胺等酰胺类;脂肪酸的甘油酯等酯类;乙腈等腈类;二甲亚砜等硫化物类等。
作为表面活性剂,例如有:烷基苯磺酸金属盐、二萘甲烷二磺酸金属盐、醇硫酸酯/盐、烷基芳基磺酸盐、木素磺酸盐、聚氧乙二醇醚、聚氧乙烯烷基芳基醚、聚氧乙烯山梨糖醇酐单烷基酯、萘磺酸甲醛缩合物的盐等。
作为其它的辅助剂,例如有:羧甲基纤维素、阿拉伯胶、海藻酸钠、瓜尔胶、黄蓍胶、聚乙烯醇等粘合剂或增粘剂;金属皂等消泡剂;脂肪酸、烷基磷酸盐、硅酮、石蜡等物性改善剂;着色剂等。
进而,本发明的农业或园艺用植物病害防除剂,在上述各种制剂形态中,除添加作为有效成分的本发明化合物以外,根据需要还可以混合其他公知的活性化合物,例如杀虫剂、杀螨剂、昆虫生长调节剂、杀线虫剂、杀菌剂、植物病害防除剂、除草剂、植物生长调节剂、肥料及土壤改良剂等。
本发明的农业或园艺用植物病害防除剂可以通过以下方式进行使用:将它们的制剂直接或稀释后散布于茎叶上、对种子进行处理、施用于土壤中、施用于水面或施用于育苗箱等。它们的施用量根据所用化合物的种类、目标病害、虫害动向、受害程度、环境条件、所使用的剂型等的不同而不同。
例如,在直接使用粉剂、颗粒剂时,每10公亩使用有效成分0.1g~5kg,优选为1g~1kg的范围。
此外,如乳剂、水合剂那样在液体状态下使用时,每10公亩使用有效成分0.1ppm~10,000ppm,优选为10~3,000ppm的范围。
此外,在施用于育苗箱时,通过进行抑制化合物溶出的制剂化,可以长时间地赋予病害防除效果。
本发明的农业或园艺用植物病害防除剂通过采用上述施用形态,可以防除丝状菌、细菌及病毒等引起的植物病害。
下面将具体的病害作为非限定例给出。
黄瓜霜霉病(Pseudoperonospora cubensis),苹果黑星病(Venturia inaequalis),黄瓜白粉病(Sphaerotheca cucurbitae),小麦白粉病(Erysiphe graminis),小麦颖枯病(Septoria nodorum),稻瘟病(Pyricularia oryzae),黄瓜灰霉病(Botrytis cinerea),水稻纹枯病(Rhizoctonia solani),小麦叶锈病(Puccinia recondita),黄瓜细菌性斑点病(Pseudomonas syringe),水稻白叶枯病(Xanthomonas oryzae),水稻细菌性谷枯病(Burkholderia glumae),水稻苗细菌性立枯病(Burkholderia plantarii),水稻褐斑病(Acidovorax avenae),内颖褐变病(Erwinia ananas),黄瓜炭疽病(Colletotrichum orbiculare)
实施例
下面通过实施例对本发明的农业或园艺用植物病害防除剂中使用的通式[I]表示的苯并异噻唑衍生物的制造方法及制剂化方法进行详细的说明,但本发明并不限定于这些实施例。予以说明,以下说明中“%”表示重量百分比。
[实施例1]
3-(3,4-二氯异噻唑-5-基甲氧基)-1,2-苯并异噻唑-1,1-二氧化物的制造(本发明化合物编号1)
在4.0g(20.3mmol)3,4-二氯异噻唑-5-羧酸中加入8ml草酰氯和催化剂量的DMF,于50℃下搅拌30分钟。将反应混合物在减压下浓缩,得到3,4-二氯异噻唑-5-碳酰氯。
使1.9g(50.5mmol)硼氢化钠混悬于40ml水中,在10~15℃向该混悬液中滴入上述制得的3,4-二氯异噻唑-5-碳酰氯的THF(4ml)溶液。于15℃下搅拌30分钟,然后添加柠檬酸水溶液使溶液为弱酸性,用乙酸乙酯萃取。水洗有机层,用无水硫酸镁进行干燥、浓缩。用己烷洗涤所得结晶,得到3.0g(收率81%)的(3,4-二氯异噻唑-5-基)甲醇的无色结晶(熔点94-95℃)。
1H-NMR(CDCl3)δ:2.28(1H,bs),4.96(2H,s)ppm
在6ml乙腈中溶解3-氯-1,2-苯并异噻唑-1,1-二氧化物0.62g(3.10mmol)及(3,4-二氯异噻唑-5-基)甲醇0.57g(3.10mmol),向该溶液中滴入0.34g(3.4mmol)三乙胺,于室温下搅拌5小时。反应结束后,添加12ml水,过滤结晶。用水和异丙醇洗涤所得结晶,得到0.89g(收率82%)的3-(3,4-二氯异噻唑-5-基甲氧基)-1,2-苯并异噻唑-1,1-二氧化物的无色粉末(熔点165-167℃)。
1H-NMR(CDCl3)δ:5.79(2H,s),7.73-7.94(4H,m)ppm
[实施例2]
3-(3-甲基异噻唑-5-基甲氧基)-1,2-苯并异噻唑-1,1-二氧化物的制造(本发明化合物编号5)
在8ml乙腈中溶解3-氯-1,2-苯并异噻唑-1,1-二氧化物0.78g(3.88mmol)及(3-甲基异噻唑-5-基)甲醇0.50g(3.88mmol),向该溶液中滴入0.51g(5.0mmol)三乙胺,于室温下搅拌5小时。反应结束后,添加16ml水,过滤结晶。用水和异丙醇洗涤所得结晶,得到0.30g(收率26%)的3-(3-甲醇异噻唑-5-基甲氧基)-1,2-苯并异噻唑-1,1-二氧化物的淡褐色粉末(熔点202-204℃)。
1H-NMR(CDCl3)δ:2.53(3H,s),5.82(2H,s),7.15(1H,s),7.70-7.93(4H,m)ppm
下面给出代表性的制剂例来具体说明制剂方法。化合物、添加剂的种类及配合比例不限定于以下的范围,可以在更宽的范围进行变更。以下说明中的“份”表示重量份。
[实施例3]粉剂
化合物编号1的化合物 2份
硅藻土 5份
粘土 93份
将上述成分均匀地混合粉碎,制成粉剂。此外,分别使用表1所记载的化合物代替化合物编号1,同样可以制得粉剂。
[实施例4]水合剂
化合物编号1的化合物 50份
硅藻土 45份
二萘甲烷二磺酸钠 2份
木质素磺酸钠 3份
将上述成分均匀地混合粉碎,制成水合剂。此外,分别使用表1所记载的化合物代替化合物编号1,同样可以制得水合剂。
[实施例5]水合剂
化合物编号1的化合物 10份
粘土 69份
硅藻土 20份
β-萘磺酸甲醛缩合物钠盐 0.5份
聚氧乙烯辛基苯基醚 0.5份
将上述成分均匀地混合粉碎,制成水合剂。此外,分别使用表1所记载的化合物代替化合物编号1,同样可以制得水合剂。
[实施例6]乳剂
化合物编号1的化合物 30份
环己酮 20份
聚氧乙烯烷基芳基醚 11份
烷基苯磺酸钙 4份
甲基萘 35份
将上述成分均匀地溶解,制成乳剂。此外,分别使用表1所记载的化合物代替化合物编号1,同样可以制得乳剂。
[实施例7]颗粒剂
化合物编号1的化合物 4份
月桂醇硫酸酯的钠盐 2份
木质素磺酸钠 5份
羧甲基纤维素 2份
粘土 87份
将上述成分均匀混合并粉碎。向该混合物中添加相当于20份的量的水进行捏合,使用挤出式制粒机将其加工成14~32目的颗粒,然后进行干燥,制成颗粒剂。此外,分别使用表1所记载的化合物代替化合物编号1,同样可以制得颗粒剂。
下面给出试验例对本发明的农业或园艺用植物病害防除剂的效果进行具体说明。
[试验例1]稻瘟病移植时的根部处理试验
以有效成分浓度为每10公亩30g的比例用水稀释按照实施例5的操作制得的水合剂,将250μ1该药液施用于3叶期的水稻(品种:爱知旭)的根部。2小时后,分别将水稻移植到直径9cm的白瓷钵的4个地方,其中,每3茎水稻移植到一个地方,在温室内培育。处理26日后,喷雾接种稻瘟病菌(Pyricularia oryzae)的分生孢子混悬液,然后立即放入25℃的湿室内,放置24小时。之后,将其移入温室内,接种8日后,查出接种时的最高位叶的病斑数。通过以下的数学式求出防除值(也称保护值),利用表2的基准进行评价。结果示于表3。
[数1]
[表2]
评价 |
A:防除值为90.0%以上~100%B:防除值为80.0%以上、小于90.0%C:防除值为50.0%以上、小于80.0%D:防除值小于50.0% |
另外,使用以下所示的比较化合物,按照实施例5制备水合剂,与上述试验例同样操作,求出防除值,结果示于表3。
[化4]
比较化合物1
(非专利文献1、专利文献1中记载的)
[表3]
化合物编号 | 评价 |
1 | B |
5 | B |
比较化合物1 | C |
对照化合物烯丙异噻唑 | C |
[试验例2]黄瓜炭疽病预防效果试验
在直径5.5cm的塑料杯中以播种深度2cm播种黄瓜种子(品种:相模半白(Sagamihanjiro)),每次播种4粒,在温室内培育7天。按照实施例5制备水合剂,以有效成分为指定浓度的方式用水稀释该水合剂,以每杯10ml的量将该水合剂灌注到子叶展开了的黄瓜幼苗的根部土壤中。7日后,以手撒的方式将在PDA平板培养基上培养的黄瓜炭疽病菌(Colletotrichum orbiculare)的分生孢子混悬液(105~106个/ml)喷雾到黄瓜植物体上,进行接种,在25℃的湿室中放置24小时。然后,在玻璃温室内的水盘上静置,7日后检查钵中所有的子叶的病斑数。用上述数学式1求出防除值,按照表2的基准进行评价。结果示于表4。
此外,使用以下所示的比较化合物,按照实施例5制备水合剂,与上述试验例同样操作,求出防除值,结果示于表4。
[化5]
(非专利文献1、专利文献1中记载的)
[表4]
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- 2007-04-20 JP JP2008514379A patent/JP5089581B2/ja active Active
- 2007-04-20 WO PCT/JP2007/000432 patent/WO2007129454A1/ja active Application Filing
- 2007-04-20 CN CN2007800166486A patent/CN101437806B/zh active Active
- 2007-04-20 US US12/225,868 patent/US7714140B2/en active Active
- 2007-04-20 KR KR1020087026911A patent/KR101319063B1/ko active Protection Beyond IP Right Term
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CN101437806A (zh) | 2009-05-20 |
PL2017268T3 (pl) | 2013-06-28 |
EP2017268A4 (en) | 2010-05-19 |
TWI369355B (zh) | 2012-08-01 |
EP2017268A1 (en) | 2009-01-21 |
JP5089581B2 (ja) | 2012-12-05 |
EP2017268B1 (en) | 2013-01-16 |
KR20090010179A (ko) | 2009-01-29 |
TW200808789A (en) | 2008-02-16 |
US20090137646A1 (en) | 2009-05-28 |
KR101319063B1 (ko) | 2013-10-17 |
JPWO2007129454A1 (ja) | 2009-09-17 |
WO2007129454A1 (ja) | 2007-11-15 |
US7714140B2 (en) | 2010-05-11 |
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