CN109906221A - N-烷基磺酰基吲哚啉化合物以及含有该化合物的农业园艺用杀虫剂及其使用方法 - Google Patents
N-烷基磺酰基吲哚啉化合物以及含有该化合物的农业园艺用杀虫剂及其使用方法 Download PDFInfo
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- CN109906221A CN109906221A CN201780067658.6A CN201780067658A CN109906221A CN 109906221 A CN109906221 A CN 109906221A CN 201780067658 A CN201780067658 A CN 201780067658A CN 109906221 A CN109906221 A CN 109906221A
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- alkyl
- halogenated
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Classifications
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- 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
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- 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
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
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- A61K31/5025—Pyridazines; Hydrogenated pyridazines ortho- or peri-condensed with heterocyclic ring systems
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
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- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
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Abstract
在农业及园艺等作物生产中,由害虫等导致的灾害在现在仍然较大,出于对现有药物具有抗性的害虫的产生等主要原因,期望开发出新型的农业园艺用杀虫剂。本发明提供一种以下述通式(1)所表示的吲哚啉化合物或其盐作为有效成分的农业园艺用杀虫剂及其使用方法。[化学式1]通式(1)中,R1及R4为氢原子,R2及R3为卤原子,R5为卤代烷基,Ra、Rb及Rc为氢原子,A1为CH基,A2为氮原子,A3为N‑Me,m为2,n为1。
Description
技术领域
本发明涉及特定的N-烷基磺酰基、亚磺酰基或硫代吲哚啉化合物或其盐,以及含有该化合物或其盐作为有效成分的农业园艺用杀虫剂及其使用方法。
背景技术
迄今为止,人们研究了作为农业园艺用杀虫剂的各种各样的化合物,有报告指出某种缩合杂环化合物作为杀虫剂是有用的(例如,参照专利文献1~8)。这些文献中,专利文献8中公开了一种化合物,其具有两种缩合杂环相互结合而成的结构,但该文献中未公开由N-烷基磺酰基、亚磺酰基或硫代吲哚啉环形成的缩合杂环化合物。
现有技术文献
专利文献
专利文献1:日本特开2009-280574号公报
专利文献2:日本特开2010-275301号公报
专利文献3:日本特开2011-79774号公报
专利文献4:日本特开2012-131780号公报
专利文献5:国际公开第2012/086848号册
专利文献6:国际公开第2013/018928号册
专利文献7:国际公开第2014/157600号册
专利文献8:国际公开第2016/091731号册
发明内容
本发明要解决的技术问题
在农业及园艺等作物生产中,由害虫等导致的灾害在现在仍然较大,出于对现有药物具有抗性的害虫的产生等主要原因,希望开发出新型的农业园艺用杀虫剂及杀螨剂。此外,由于务农者的高龄化,还谋求各种省力的施用方法,并同时谋求创造出具有适合这些施用方法的特性的农业园艺用杀虫剂。
解决技术问题的技术手段
本申请的发明人为了开发新型的农业园艺用杀虫剂进行了仔细研究,结果发现,本发明的通式(1)所表示的吲哚啉化合物或其盐类作为农业园艺用杀虫剂是有用的,从而完成了本发明。
即,本发明涉及:
[1]一种下述通式(1)所表示的吲哚啉化合物或其盐,
[化学式1]
通式(1)中,R1及R4可相同也可不同,其表示:(a1)氢原子;(a2)卤原子、(a3)(C1-C6)烷基;或(a4)(C1-C6)烷氧基,
R2及R3可相同也可不同,其表示:(b1)氢原子;(b2)卤原子;(b3)氰基;(b4)硝基;(b5)甲酰基;(b6)(C1-C6)烷基;(b7)(C3-C6)环烷基;(b8)(C1-C6)烷氧基;(b9)(C1-C6)烷氧基(C1-C6)烷基;(b10)卤代(C1-C6)烷基;(b11)卤代(C1-C6)烷氧基;(b12)(C1-C6)烷硫基;(b13)(C1-C6)烷基亚磺酰基;(b14)(C1-C6)烷基磺酰基;(b15)卤代(C1-C6)烷硫基;(b16)卤代(C1-C6)烷基亚磺酰基;(b17)卤代(C1-C6)烷基磺酰基;(b18)(C1-C6)烷氧基羰基;(b19)R8(R9)N基,其中,R8及R9可相同也可不同,其表示:氢原子、(C1-C6)烷基、(C2-C6)烯基、(C2-C6)炔基、(C3-C6)环烷基、(C3-C6)环烷基(C1-C6)烷基、(C1-C6)烷氧基(C1-C6)烷基、卤代(C1-C6)烷基、卤代(C1-C6)烷氧基(C1-C6)烷基、(C1-C6)烷基羰基、苯基或苯基(C1-C6)烷基;(c20)R8(R9)N羰基,其中,R8及R9与所述R8及R9相同;(b21)C(R8)=NOR9基,其中,R8及R9与所述R8及R9相同;(b22)苯基;(b23)在环上具有选自(a)卤原子、(b)氰基、(c)硝基、(d)甲酰基、(e)(C1-C6)烷基、(f)卤代(C1-C6)烷基、(g)(C1-C6)烷氧基、(h)卤代(C1-C6)烷氧基、(i)(C3-C6)环烷基(C1-C6)烷氧基、(j)(C1-C6)烷硫基、(k)卤代(C1-C6)烷硫基、(l)(C1-C6)烷基亚磺酰基、(m)卤代(C1-C6)烷基亚磺酰基、(n)(C1-C6)烷基磺酰基或(o)卤代(C1-C6)烷基磺酰基中的可相同也可不同的1~5个取代基的苯基;(b24)苯基(C1-C6)烷基;或(b25)在环上具有选自(a)卤原子、(b)氰基、(c)硝基、(d)甲酰基、(e)(C1-C6)烷基、(f)卤代(C1-C6)烷基、(g)(C1-C6)烷氧基、(h)卤代(C1-C6)烷氧基、(i)(C3-C6)环烷基(C1-C6)烷氧基、(j)(C1-C6)烷硫基、(k)卤代(C1-C6)烷硫基、(l)(C1-C6)烷基亚磺酰基、(m)卤代(C1-C6)烷基亚磺酰基、(n)(C1-C6)烷基磺酰基或(o)卤代(C1-C6)烷基磺酰基中的可相同也可不同的1~5个取代基的苯基(C1-C6)烷基,
R5可相同也可不同,其表示:(c1)卤代(C1-C6)烷基;(c2)卤代(C1-C6)烷氧基;(c3)卤代(C1-C6)烷硫基;(c4)卤代(C1-C6)烷基亚磺酰基;或(c5)卤代(C1-C6)烷基磺酰基,
Ra及Rb可相同也可不同,其表示:(d1)氢原子;(d2)卤原子;(d3)(C1-C6)烷基;(d4)(C1-C6)烷氧基;(d5)氰基;或(d6)(C1-C6)烷氧基羰基,或者Ra及Rb可结合形成3~6元的脂肪族环、或者Ra及Rb可与1个氧原子或硫原子键合,
Rc表示:(d1)氢原子;(d2)卤原子;(d3)(C1-C6)烷基;(d4)(C1-C6)烷氧基;或(d6)(C1-C6)烷氧基羰基,
A1及A2表示氮原子或C-R6,A3表示氧原子、硫原子或N-R7,其中,R6及R7可相同也可不同,其表示:(e1)氢原子;(e2)卤原子;(e3)氰基;(e4)硝基;(e5)(C1-C6)烷基;或(e6)(C1-C6)烷氧基,
m表示0、1或2,n表示1或2,
Et表示乙基。
[2]根据[1]所述的吲哚啉化合物或其盐,其中,
R1及R4可相同也可不同,其表示(a1)氢原子或(a2)卤原子,
R2及R3可相同也可不同,其表示:(b1)氢原子;(b2)卤原子;(b3)氰基;(b5)甲酰基;(b6)(C1-C6)烷基;(b7)(C3-C6)环烷基;(b8)(C1-C6)烷氧基;(b10)卤代(C1-C6)烷基;(b11)卤代(C1-C6)烷氧基;(b12)(C1-C6)烷硫基;(b15)卤代(C1-C6)烷硫基;(b18)(C1-C6)烷氧基羰基;(b19)R8(R9)N基,其中,R8及R9与所述R8及R9相同;(c20)R8(R9)N羰基,其中,R8及R9与所述R8及R9相同;或(b21)C(R8)=NOR9基,其中,R8及R9与所述R8及R9相同,
R5可相同也可不同,其表示:(c1)卤代(C1-C6)烷基;(c3)卤代(C1-C6)烷硫基;(c4)卤代(C1-C6)烷基亚磺酰基或(c5)卤代(C1-C6)烷基磺酰基,
Ra、Rb及Rc表示(d1)氢原子,
A1及A2表示氮原子或C-R6,A3表示氧原子、硫原子或N-R7,其中,R6及R7与所述R6及R7相同,
m表示2,n表示1。
[3]根据[1]所述的吲哚啉化合物或其盐,其中,
R1及R4表示(a1)氢原子或(a2)卤原子,
R2及R3可相同也可不同,其表示:(b1)氢原子;(b2)卤原子;或(b7)(C3-C6)环烷基;(b10)卤代(C1-C6)烷基;或(b11)卤代(C1-C6)烷氧基,
R5可相同也可不同,其表示:(c1)卤代(C1-C6)烷基;或(c3)卤代(C1-C6)烷硫基;(c4)卤代(C1-C6)烷基亚磺酰基或(c5)卤代(C1-C6)烷基磺酰基,
Ra、Rb及Rc表示(d1)氢原子,
A1及A2表示氮原子或C-R6,A3表示氧原子或N-R7,其中,R6及R7与所述R6及R7相同,
m表示2,n表示1。
[4]一种农业园艺用杀虫剂,其特征在于,其含有[1]~[3]中任一项所述的化合物作为有效成分。
[5]一种农业园艺用杀虫剂的使用方法,其特征在于,以[1]~[3]中任一项所述的化合物的有效量对植物或土壤进行处理。
[6]一种动物用的外部寄生虫防除剂,其特征在于,其含有[1]~[3]中任一项所述的化合物作为有效成分。
发明效果
本发明的吲哚啉化合物或其盐类作为农业园艺用杀虫剂具有优异的效果。此外,对寄生在狗、猫这样的玩赏动物,或者牛、羊等家畜上的害虫也具有效果。
具体实施方式
在本申请发明化合物的通式(1)的定义中,“卤代”是指“卤原子”,其表示氯原子、溴原子、碘原子或氟原子。
“(C1-C6)烷基”例如表示甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、正戊基、异戊基、叔戊基、新戊基、2,3-二甲基丙基、1-乙基丙基、1-甲基丁基、2-甲基丁基、正己基、异己基、2-己基、3-己基、2-甲基戊基、3-甲基戊基、1,1,2-三甲基丙基、3,3-二甲基丁基等直链或支链状的碳原子数为1~6个的烷基。
“(C2-C6)烯基”例如表示乙烯基、烯丙基、异丙烯基、1-丁烯基、2-丁烯基、2-甲基-2-丙烯基、1-甲基-2-丙烯基、2-甲基-1-丙烯基、戊烯基、1-己烯基、3,3-二甲基-1-丁烯基等直链或支链状的碳原子数为2~6个的烯基,“(C2-C6)炔基”例如表示乙炔基、1-丙炔基、2-丙炔基、1-丁炔基、2-丁炔基、3-丁炔基、3-甲基-1-丙炔基、2-甲基-3-丙炔基、戊炔基、1-己炔基、3-甲基-1-丁炔基、3,3-二甲基-1-丁炔基等直链或支链状的碳原子数为2~6个的炔基。
“(C3-C6)环烷基”例如表示环丙基、环丁基、环戊基、环己基等碳原子数为3~6个的环状烷基,“(C1-C6)烷氧基”例如表示甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、仲丁氧基、叔丁氧基、正戊氧基、异戊氧基、叔戊氧基、新戊氧基、2,3-二甲基丙氧基、1-乙基丙氧基、1-甲基丁氧基、正己氧基、异己氧基、1,1,2-三甲基丙氧基等直链或支链状的碳原子数为1~6个的烷氧基。
“(C2-C6)烯氧基”例如表示丙烯氧基、丁烯氧基、戊烯氧基、己烯氧基等直链或支链状的碳原子数为2~6个的烯氧基,“(C2-C6)炔氧基”例如表示丙炔氧基、丁炔氧基、戊炔氧基、己炔氧基等直链或支链状的碳原子数为2~6个的炔氧基。
“(C1-C6)烷硫基”例如表示甲硫基、乙硫基、正丙硫基、异丙硫基、正丁硫基、仲丁硫基、叔丁硫基、正戊硫基、异戊硫基、叔戊硫基、新戊硫基、2,3-二甲基丙硫基、1-乙基丙硫基、1-甲基丁硫基、正己硫基、异己硫基、1,1,2-三甲基丙硫基等直链或支链状的碳原子数为1~6个的烷硫基。
“(C1-C6)烷基亚磺酰基”例如表示甲基亚磺酰基、乙基亚磺酰基、正丙基亚磺酰基、异丙基亚磺酰基、正丁基亚磺酰基、仲丁基亚磺酰基、叔丁基亚磺酰基、正戊基亚磺酰基、异戊基亚磺酰基、叔戊基亚磺酰基、新戊基亚磺酰基、2,3-二甲基丙基亚磺酰基、1-乙基丙基亚磺酰基、1-甲基丁基亚磺酰基、正己基亚磺酰基、异己基亚磺酰基、1,1,2-三甲基丙基亚磺酰基等直链或支链状的碳原子数为1~6个的烷基亚磺酰基。
“(C1-C6)烷基磺酰基”例如表示甲基磺酰基、乙基磺酰基、正丙基磺酰基、异丙基磺酰基、正丁基磺酰基、仲丁基磺酰基、叔丁基磺酰基、正戊基磺酰基、异戊基磺酰基、叔戊基磺酰基、新戊基磺酰基、2,3-二甲基丙基磺酰基、1-乙基丙基磺酰基、1-甲基丁基磺酰基、正己基磺酰基、异己基磺酰基、1,1,2-三甲基丙基磺酰基等直链或支链状的碳原子数为1~6个的烷基磺酰基。
“(C1-C6)烷基羰基”例如表示甲基羰基、乙基羰基、正丙基羰基、异丙基羰基、正丁基羰基、仲丁基羰基、叔丁基羰基、正戊基羰基、异戊基羰基、叔戊基羰基、新戊基羰基、2,3-二甲基丙基羰基、1-乙基丙基羰基、1-甲基丁基羰基、正己基羰基、异己基羰基、1,1,2-三甲基丙基羰基等直链或支链状的碳原子数为1~6个的烷基羰基,“(C1-C6)烷氧基羰基”例如表示甲氧基羰基、乙氧基羰基、正丙氧基羰基、异丙氧基羰基、正丁氧基羰基、仲丁氧基羰基、叔丁氧基羰基、正戊氧基羰基、异戊氧基羰基、叔戊氧基羰基、新戊氧基羰基、2,3-二甲基丙氧基羰基、1-乙基丙氧基羰基、1-甲基丁氧基羰基、正己氧基羰基、异己氧基羰基、1,1,2-三甲基丙氧基羰基等直链或支链状的碳原子数为1~6个的烷氧基羰基。
在上述“(C1-C6)烷基”、“(C2-C6)烯基”、“(C2-C6)炔基”、“(C3-C6)环烷基”、“(C1-C6)烷氧基”、“(C2-C6)烯氧基”、“(C2-C6)炔氧基”、“(C1-C6)烷硫基”、“(C1-C6)烷基亚磺酰基”、“(C1-C6)烷基磺酰基”、“(C2-C6)烯基硫基”、“(C2-C6)烯基亚磺酰基”、“(C2-C6)烯基磺酰基”、“(C2-C6)炔基硫基”、“(C2-C6)炔基亚磺酰基”、“(C2-C6)炔基磺酰基”、“(C3-C6)环烷基硫基”、“(C3-C6)环烷基亚磺酰基”或“(C3-C6)环烷基磺酰基”的氢原子可被取代的位置上,可取代1个或2个以上的卤原子,取代的卤原子为2个以上时,卤原子可相同也可不同。
所述被卤原子取代的基团可分别表示为“卤代(C1-C6)烷基”、“卤代(C2-C6)烯基”、“卤代(C2-C6)炔基”、“卤代(C3-C6)环烷基”、“卤代(C1-C6)烷氧基”、“卤代(C2-C6)烯氧基”、“卤代(C2-C6)炔氧基”、“卤代(C3-C6)环烷氧基”、“卤代(C1-C6)烷硫基”、“卤代(C1-C6)烷基亚磺酰基”、“卤代(C1-C6)烷基磺酰基”、“卤代(C2-C6)烯基硫基”、“卤代(C2-C6)烯基亚磺酰基”、“卤代(C2-C6)烯基磺酰基”、“卤代(C2-C6)炔基硫基”、“卤代(C2-C6)炔基亚磺酰基”、“卤代(C2-C6)炔基磺酰基”、“卤代(C3-C6)环烷基硫基”、“卤代(C3-C6)环烷基亚磺酰基”或“卤代(C3-C6)环烷基磺酰基”。
“(C1-C6)”、“(C2-C6)”、“(C3-C6)”等表达方式表示各种取代基的碳原子数的范围。进一步,上述取代基所连接的基团也可表示上述定义,例如,“(C1-C6)烷氧基(C1-C6)烷基”表示直链或支链状的碳原子数为1~6个的烷氧基与直链或支链状的碳原子数为1~6个的烷基键合。
作为本发明的通式(1)所表示的吲哚啉化合物的盐类,例如可例示出盐酸盐、硫酸盐、硝酸盐、磷酸盐等无机酸盐类,乙酸盐、富马酸盐、马来酸盐、草酸盐、甲磺酸盐、苯磺酸盐、对甲苯磺酸盐等有机酸盐类,钠离子、钾离子、钙离子、三甲铵等与无机或有机碱的盐类。
对于本发明的通式(1)所表示的吲哚啉化合物或其盐类,其结构式中有时存在一个或多个手性中心,有时也存在两种以上的光学异构体及非对映异构体,本发明包含全部的各种光学异构体及以任意比例含有它们的混合物。此外,对于本发明的通式(1)所表示的吲哚啉化合物或其盐类,其结构式中有时还存在来自碳碳双键的两种几何异构体,本发明包含全部的各种几何异构体及以任意比例含有它们的混合物。
在本发明的通式(1)所表示的吲哚啉化合物中,优选:R1及R4可相同也可不同,其为(a1)氢原子或(a2)卤原子,R2及R3可相同也可不同,其为:(b1)氢原子;(b2)卤原子;(b3)氰基;(b5)甲酰基;(b6)(C1-C6)烷基;(b7)(C3-C6)环烷基;(b8)(C1-C6)烷氧基;(b10)卤代(C1-C6)烷基;(b11)卤代(C1-C6)烷氧基;(b12)(C1-C6)烷硫基;(b15)卤代(C1-C6)烷硫基;(b18)(C1-C6)烷氧基羰基;(b19)R8(R9)N基,其中,R8及R9与所述R8及R9相同;(c20)R8(R9)N羰基,其中,R8及R9与所述R8及R9相同;或(b21)C(R8)=NOR9基,其中,R8及R9与所述R8及R9相同,R5可相同也可不同,其为:(c1)卤代(C1-C6)烷基;(c3)卤代(C1-C6)烷硫基;(c4)卤代(C1-C6)烷基亚磺酰基;或(c5)卤代(C1-C6)烷基磺酰基,Ra、Rb及Rc为(d1)氢原子,A1及A2为氮原子或C-R6,A3为氧原子或N-R7,其中,R6及R7与所述R6及R7相同,m为2,n为1。
进一步优选:R1及R4为(a1)氢原子或(a2)卤原子,R2及R3可相同也可不同,其为:(b1)氢原子;(b2)卤原子;(b7)(C3-C6)环烷基;(b10)卤代(C1-C6)烷基;或(b11)卤代(C1-C6)烷氧基,R5可相同也可不同,其为:(c1)卤代(C1-C6)烷基;(c3)卤代(C1-C6)烷硫基;(c4)卤代(C1-C6)烷基亚磺酰基;或(c5)卤代(C1-C6)烷基磺酰基,Ra、Rb及Rc为(d1)氢原子,A1及A2为氮原子或C-R6,A3为氧原子或N-R7,其中,R6及R7与所述R6及R7相同,m为2,n为1。在本公开中,Et表示乙基。
本发明的各种化合物例如可通过下述制备方法进行制备,但本发明并不受其限定。
制备方法1
[化学式2]
式中,R1、R2、R3、R4、R5、Ra、Rb、Rc、A1、A2、A3及n与所述R1、R2、R3、R4、R5、Ra、Rb、Rc、A1、A2、A3及n相同。
工序[a]的制备方法
在惰性溶剂存在下,使通式(2-4)所表示的吲哚啉羧酸与卤化剂反应,由此制备羧酸卤化物(carboxylic halide)。
作为在本反应中使用的卤化剂,可列举出五氯化磷、氯化亚砜、三氯氧磷及草酰氯等。相对于通式(2-4)所表示的吲哚啉化合物羧酸,其使用量从1倍摩尔~5倍摩尔的范围中适当选择并使用即可。
作为可在本反应中使用的惰性溶剂,只要不显著阻碍本反应即可,例如可列举出苯、甲苯、二甲苯等芳香族烃类、二氯甲烷、氯仿、四氯化碳等卤化烃类、氯苯、二氯苯等卤化芳香族烃类等,这些惰性溶剂可单独使用或混合使用两种以上。此外,也可不使用溶剂。
本反应的反应温度通常在约0℃~所使用的溶剂的沸点的范围中进行即可,反应时间根据反应规模、反应温度等变化,虽然不固定,但在数分钟~48小时的范围中适当选择即可。
反应结束后,通过常规方法分离目标产物即可,可根据需要,通过利用再结晶、蒸馏等进行提纯而制备目标产物。或者也可不进行分离而用于下个工序。
工序[B]的制备方法
对于通式(2-5)所表示的吲哚啉羧酸酰胺化合物,可通过在惰性溶剂及碱的存在下使上述工序中制备的吲哚啉羧酸卤化物与通式(3)所表示的胺类反应,从而制备通式(2-5)所表示的吲哚啉羧酸酰胺化合物。
作为可在本反应中使用的碱,可列举出碳酸锂、碳酸氢锂、碳酸钠、碳酸氢钠、碳酸钾、碳酸氢钾、碳酸钙、碳酸镁等碳酸盐,乙酸锂、乙酸钠、乙酸钾等乙酸盐,吡啶、皮考啉、卢剔啶、三乙胺、三丁胺、二异丙基乙胺等有机碱等。
作为可在本反应中使用的惰性溶剂,只要不显著阻碍本反应即可,例如可列举出苯、甲苯、二甲苯等芳香族烃类、二氯甲烷、氯仿、四氯化碳等卤化烃类、氯苯、二氯苯等卤化芳香族烃类、二乙醚、四氢呋喃(THF)、二氧杂环己烷等链状或环状醚类、乙腈、丙腈等腈类、乙酸甲酯等酯类、N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、二甲基亚砜、1,3-二甲基-2-咪唑啉酮等极性溶剂等,这些惰性溶剂可单独使用或混合使用两种以上。
由于本反应为等摩尔反应,因此以等摩尔使用各化合物即可,也可过量使用任一种化合物。本反应的反应温度通常在约0℃~所使用的溶剂的沸点的范围中进行即可,反应时间根据反应规模、反应温度等变化,虽然不固定,但在数分钟~48小时的范围中适当选择即可。
反应结束后,通过常规方法从含有目标产物的反应系中分离通式(2-5)所表示的吲哚啉羧酸酰胺化合物即可,可根据需要,通过利用再结晶、层析法等进行提纯而制备目标产物。或者也可不进行分离而用于下个工序。
工序[C]的制备方法
可通过下述方式制备通式(1-1)所表示的吲哚啉化合物:在惰性溶剂的存在下,使上述工序中制备的通式(2-5)所表示的吲哚啉羧酸酰胺化合物与酸反应;或者在惰性溶剂的存在下,使上述工序中制备的通式(2-5)所表示的吲哚啉羧酸酰胺化合物与酸及缩合剂反应。
作为在本反应中使用的酸,例如可例示出盐酸、硫酸、硝酸等无机酸、甲酸、乙酸、丙酸、三氟乙酸、苯甲酸等有机酸、甲磺酸、三氟甲磺酸等磺酸、磷酸等,相对于通式(2-5)所表示的吲哚啉羧酸化合物,其使用量在0.01倍摩尔~10倍摩尔的范围中适当选择并使用即可。
作为在本反应中使用的惰性溶剂,只要不显著阻碍本反应的进行即可,例如可例示出苯、甲苯、二甲苯等芳香族烃类、二氯甲烷、氯仿、四氯化碳等卤化烃类;氯苯、二氯苯等卤化芳香族烃类、二乙醚、甲基叔丁醚、二氧杂环己烷、四氢呋喃等链状或环状醚类、乙酸乙酯等酯类、二甲基甲酰胺、二甲基乙酰胺等酰胺类、丙酮、甲基乙基酮等酮类、二甲基亚砜、1,3-二甲基-2-咪唑啉酮等极性溶剂等的惰性溶剂,这些惰性溶剂可单独使用或混合使用两种以上。
本反应的反应温度通常在约0℃~所使用的溶剂的沸点的范围中进行即可,反应时间根据反应规模、反应温度等变化,虽然不固定,但在数分钟~48小时的范围中适当选择即可。反应结束后,通过常规方法从含有目标产物的反应系中分离目标产物即可,可根据需要,通过利用再结晶、层析法等进行提纯而制备目标产物。
使用缩合剂时,作为在本反应中使用的缩合剂,例如可例示出氰代磷酸二乙酯(DEPC)、羰基二咪唑(CDI)、1,3-二环己基碳二亚胺(DCC)、氯碳酸酯类、碘代2-氯-1-甲基吡啶鎓、偶氮二羧酸双(2-甲氧基乙酯)(DMEAD)、偶氮二羧酸二乙酯(DEAD)等。相对于通式(2-5)所表示的吲哚啉羧酸化合物,其使用量在1倍摩尔~1.5倍摩尔的范围中适当选择并使用即可。在使用DMEAD或DEAD时,可组合使用三苯基膦、三环己基膦等膦类,相对于DMEAD或DEAD,其使用量可在1倍摩尔~1.5倍摩尔的范围中适当选择。
作为在本反应中使用的惰性溶剂,只要不显著阻碍本反应的进行即可,例如可例示出苯、甲苯、二甲苯等芳香族烃类、二氯甲烷、氯仿、四氯化碳等卤化脂肪族烃类;氯苯、二氯苯等卤化芳香族烃类、二乙醚、甲基叔丁醚、二氧杂环己烷、四氢呋喃等链状或环状醚类、乙酸乙酯等酯类、二甲基甲酰胺、二甲基乙酰胺等酰胺类、丙酮、甲基乙基酮等酮类、二甲基亚砜、1,3-二甲基-2-咪唑啉酮等极性溶剂等的惰性溶剂,这些惰性溶剂可单独使用或混合使用两种以上。
本反应的反应温度通常在约0℃~所使用的溶剂的沸点的范围中进行即可,反应时间根据反应规模、反应温度等变化,虽然不固定,但在数分钟~48小时的范围中适当选择即可。反应结束后,通过常规方法从含有目标产物的反应混合物中分离目标产物即可,可根据需要,通过利用再结晶、层析法等进行提纯而制备目标产物。
制备方法2
[化学式3]
式中,R5、Ra、Rb、Rc、A1、A2、A3及n与所述R5、Ra、Rb、Rc、A1、A2、A3及n相同,X表示卤原子,R21表示环丙基、环丁基、环戊基、环己基等环烷基等。
工序[D]的制备方法
在惰性溶剂存在下,使通式(1-2)所表示的吲哚啉化合物与卤化剂反应,由此可制备通式(1-2a)所表示的吲哚啉化合物。
作为在本反应中使用的卤化剂,可列举出氯、溴、碘等卤素分子类、N-氯代丁二酰亚胺(NCS)、N-溴代丁二酰亚胺(NBS)、N-碘代丁二酰亚胺(NIS)的丁二酰亚胺类、1,3-二碘-5,5-二甲基乙内酰脲(DIH)、1,3-二溴-5,5-二甲基乙内酰脲(DBH)等乙内酰脲类、磺酰氯等。相对于通式(1-2)所表示的吲哚啉化合物,其使用量在1倍摩尔~2倍尔的范围中适当选择并使用即可。
作为可在本反应中使用的惰性溶剂,只要不显著阻碍本反应即可,例如可列举出苯、甲苯、二甲苯等芳香族烃类、二氯甲烷、氯仿、四氯化碳等卤化烃类、氯苯、二氯苯等卤化芳香族烃类等,这些惰性溶剂可单独使用或混合使用两种以上。此外,也可不使用溶剂。
本反应的反应温度通常在约0℃~所使用的溶剂的沸点的范围中进行即可,反应时间根据反应规模、反应温度等变化,虽然不固定,但在数分钟~48小时的范围中适当选择即可。
反应结束后,通过常规方法从含有制备的吲哚啉化合物的反应系中分离目标产物即可,可根据需要,通过利用再结晶、蒸馏等进行提纯而制备目标产物。或者也可不进行分离而用于下个工序。
工序[E]的制备方法
可根据文献记载的方法(有机合成化学协会志Vol.69No.7 2011;Chem.Rev.2011,4475;WO2013/018928号册),在惰性溶剂的存在下,使通式(1-2a)所表示的吲哚啉化合物与通式(4)所表示的硼化合物进行交叉耦合反应,从而制备通式(1-2b)所表示的吲哚啉化合物,或在金属催化剂、碱的存在下,在惰性溶剂中使通式(1-2a)所表示的吲哚啉化合物与和通式(4)所表示的硼化合物等价的化合物(例如,环丙基环三醇硼酸钠(cyclopropylcyclic-triolborate sodium salt)等)进行交叉耦合反应,从而制备通式(1-2b)所表示的吲哚啉化合物。
作为可在本反应中使用的金属催化剂,可使用可获得的0价或2价的钯金属或盐(包括络合物)等的钯化合物,该催化剂可被担载在活性碳等上。作为优选使用的催化剂,可列举出钯(0)/碳、乙酸钯(II)、氯化钯(II)、双(三苯基膦)二氯化钯(II)、四(三苯基膦)钯(0)、[1,1’-双(二苯基膦基)二茂铁]二氯化钯(II)丙酮络合物等。
本反应也可加入配体而进行反应。作为配体,可列举出三苯基膦(PPh3)、甲基二苯基膦(Ph2PCH3)、三(2-呋喃基)膦(P(2-furyl)3)、三(邻甲苯基)膦(P(o-tol)3)、三(环己基)膦(PCy3)、二环己基苯基膦(PhPCy2)、三(叔丁基)膦(PtBu3)、2,2’-双(二苯基膦基)-1,1’-联萘(BINAP)、二苯基膦基二茂铁(DPPF)、1,1’-双(二叔丁基膦基)二茂铁(DtBPF)、N,N-二甲基-1-[2-(二苯基膦基)二茂铁基]乙胺、1-[2-(二苯基膦基)二茂铁基]乙基甲醚、4,5-双(二苯基膦)-9,9-二甲基氧杂蒽(Xantphos)等膦类配体、或咪唑-2-亚基碳烯类等类膦配体(phosphine mimic ligand)(参照德国应用化学英文版(Angewandte ChemieInternational Edition in English)第36卷,第2163页(1997年))等。
作为可在本反应中使用的碱,例如可列举出氢氧化钠、氢氧化钾、碳酸钠、碳酸钾、碳酸铯、碳酸氢钠、碳酸氢钾等无机碱类,氢化钠、氢化钾等碱金属氢化物,甲醇钠、乙醇钠、叔丁醇钾等醇盐类。
作为可在本反应中使用的惰性溶剂,只要不显著阻碍本反应即可,例如可列举出甲醇、乙醇、丙醇、丁醇、2-丙醇等醇类、二乙醚、四氢呋喃、二氧杂环己烷等链状或环状醚类、苯、甲苯、二甲苯等芳香族烃类、二氯甲烷、氯仿、四氯化碳等卤化烃类、氯苯、二氯苯等卤化芳香族烃类、乙腈等腈类、乙酸乙酯等酯类、N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、二甲基亚砜、1,3-二甲基-2-咪唑啉酮等极性溶剂,这些惰性溶剂单独使用或混合使用两种以上。
本反应的反应温度通常在约0℃~所使用的溶剂的沸点的范围中进行即可,反应时间根据反应规模、反应温度等而不固定,但在数分钟~48小时的范围中适当选择即可。相对于通式(1-2a)所表示的吲哚啉化合物,通式(4)所表示的化合物或与该化合物等价的化合物通常在约1倍摩尔~5倍摩尔的范围中使用。此外,本反应例如也可在氮气或氩气这样的非活泼气体的气氛下进行。反应结束后,通过常规方法从含有目标产物的反应混合物中分离目标产物即可,可根据需要,通过利用再结晶、层析法等进行提纯而制备目标产物。
中间体的制备方法
[化学式4]
式中,R1、R2、R3、R4、Ra、Rb、Rc、A1、A2、A3及n与所述R1、R2、R3、R4、Ra、Rb、Rc、A1、A2、A3及n相同,R例如表示甲基、乙基、正丙基、异丙基等C1-C3的烷基。
工序[α]的制备方法
在上述C1-C3的醇溶剂中,使通过国际公开第2002/030925号册或国际公开第2006/069799号册中记载的方法制备的通式(2-1)所表示的吲哚啉羧酸与氯或氯化亚砜反应,由此可制备通式(2-2)所表示的吲哚啉羧酸酯。
工序[β]的制备方法
在惰性溶剂及碱的存在下,使通式(2-2)所表示的吲哚啉羧酸酯与乙基磺酰氯反应,由此可制备通式(2-3)所表示的吲哚啉羧酸酯。
作为可在本反应中使用的惰性溶剂,只要不显著阻碍本反应即可,例如可列举出苯、甲苯、二甲苯等芳香族烃类、二氯甲烷、氯仿、四氯化碳等卤化烃类、氯苯、二氯苯等卤化芳香族烃类等、二乙醚、四氢呋喃(THF)、二氧杂环己烷等链状或环状醚类,这些惰性溶剂可单独使用或混合使用两种以上。
本反应的反应温度通常在约0℃~所使用的溶剂的沸点的范围中进行即可,反应时间根据反应规模、反应温度等变化,虽然不固定,但在数分钟~48小时的范围中适当选择即可。
反应结束后,通过常规方法分离目标产物即可,可根据需要,通过利用再结晶、蒸馏等进行提纯而制备目标产物。或者也可不进行分离而用于下个工序。
工序[γ]的制备方法
在惰性溶剂中,在水、碱的存在下,使通式(2-3)所表示的吲哚啉羧酸酯进行水解反应,由此可制备通式(2-4)所表示的吲哚啉羧酸。
作为可在本反应中使用的碱,可列举出氢氧化锂、氢氧化钠、氢氧化钾、氢氧化钙等氢氧化物、碳酸锂、碳酸氢锂、碳酸钠、碳酸氢钠、碳酸钾、碳酸氢钾、碳酸钙、碳酸镁等碳酸盐、乙酸锂、乙酸钠、乙酸钾等乙酸盐等。
作为可在本反应中使用的惰性溶剂,只要不显著阻碍本反应即可,例如可列举出甲醇、乙醇、丙醇、丁醇、2-丙醇等醇类、二乙醚、四氢呋喃(THF)、二氧杂环己烷等链状或环状醚类、N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、二甲基亚砜、1,3-二甲基-2-咪唑啉酮等、或水的极性溶剂,这些惰性溶剂可单独使用或混合使用两种以上。
本反应的反应温度通常在约0℃~所使用的溶剂的沸点的范围中进行即可,反应时间根据反应规模、反应温度等变化,虽然不固定,但在数分钟~48小时的范围中适当选择即可。反应结束后,通过常规方法从含有目标产物的反应混合物中分离目标产物即可,可根据需要,通过利用再结晶、层析法等进行提纯而制备目标产物。
以下,在表1~表10中例示出本发明的通式(1)所表示的吲哚啉化合物的代表例,但本发明并不受其限定。
表中,“Me”表示甲基,“Et”表示乙基,“Pr”表示丙基,“Ac”表示乙酰基,“c-”表示环。物性表示熔点(℃)或1H-NMR。该数据记载于表11中。
[化学式5]
[表1]
第1表
化合物编号 | R<sup>1</sup> | R<sup>2</sup> | R<sup>3</sup> | R<sup>4</sup> | R<sup>5</sup> | 物性值 |
1-1 | H | H | H | H | CF<sub>3</sub> | |
1-2 | H | F | H | H | CF<sub>3</sub> | |
1-3 | H | Cl | H | H | CF<sub>3</sub> | |
1-4 | H | Br | H | H | CF<sub>3</sub> | |
1-5 | H | I | H | H | CF<sub>3</sub> | |
1-6 | H | CF<sub>3</sub> | H | H | CF<sub>3</sub> | |
1-7 | H | CN | H | H | CF<sub>3</sub> | |
1-8 | H | Me | H | H | CF<sub>3</sub> | |
1-9 | H | OMe | H | H | CF<sub>3</sub> | |
1-10 | H | NH<sub>2</sub> | H | H | CF<sub>3</sub> | |
1-11 | H | NMe<sub>2</sub> | H | H | CF<sub>3</sub> | |
1-12 | H | NHAc | H | H | CF<sub>3</sub> | |
1-13 | H | SMe | H | H | CF<sub>3</sub> | |
1-14 | H | SCF<sub>3</sub> | H | H | CF<sub>3</sub> | |
1-15 | H | CHO | H | H | CF<sub>3</sub> | |
1-16 | H | CO<sub>2</sub>Et | H | H | CF<sub>3</sub> | |
1-17 | H | CONHMe | H | H | CF<sub>3</sub> | |
1-18 | H | CH=NOEt | H | H | CF<sub>3</sub> | |
1-19 | H | c-Pr | H | H | CF<sub>3</sub> | |
1-20 | H | H | F | H | CF<sub>3</sub> | |
1-21 | H | H | Cl | H | CF<sub>3</sub> | |
1-22 | H | H | Br | H | CF<sub>3</sub> | |
1-23 | H | H | I | H | CF<sub>3</sub> | |
1-24 | H | H | CF<sub>3</sub> | H | CF<sub>3</sub> | |
1-25 | H | H | CN | H | CF<sub>3</sub> | |
1-26 | H | H | Me | H | CF<sub>3</sub> |
[表2]
第2表
化合物编号 | R<sup>1</sup> | R<sup>2</sup> | R<sup>3</sup> | R<sup>4</sup> | R<sup>5</sup> | 物性值 |
1-27 | H | H | OMe | H | CF<sub>3</sub> | |
1-28 | H | H | NH<sub>2</sub> | H | CF<sub>3</sub> | |
1-29 | H | H | NMe<sub>2</sub> | H | CF<sub>3</sub> | |
1-30 | H | H | NHAc | H | CF<sub>3</sub> | |
1-31 | H | H | SMe | H | CF<sub>3</sub> | |
1-32 | H | H | SCF<sub>3</sub> | H | CF<sub>3</sub> | |
1-33 | H | H | CHO | H | CF<sub>3</sub> | |
1-34 | H | H | CO<sub>2</sub>Et | H | CF<sub>3</sub> | |
1-35 | H | H | CONHMe | H | CF<sub>3</sub> | |
1-36 | H | H | CH=NOEt | H | CF<sub>3</sub> | |
1-37 | H | H | c-Pr | H | CF<sub>3</sub> | |
1-38 | Cl | H | H | H | CF<sub>3</sub> | |
1-39 | H | H | H | Cl | CF<sub>3</sub> | |
1-40 | H | H | H | H | CF<sub>2</sub>CF<sub>3</sub> | 160-162 |
1-41 | H | F | H | H | CF<sub>2</sub>CF<sub>3</sub> | |
1-42 | H | Cl | H | H | CF<sub>2</sub>CF<sub>3</sub> | 88-92 |
1-43 | H | Br | H | H | CF<sub>2</sub>CF<sub>3</sub> | 173-174 |
1-44 | H | I | H | H | CF<sub>2</sub>CF<sub>3</sub> | |
1-45 | H | CF<sub>3</sub> | H | H | CF<sub>2</sub>CF<sub>3</sub> | NMR |
1-46 | H | CN | H | H | CF<sub>2</sub>CF<sub>3</sub> | |
1-47 | H | Me | H | H | CF<sub>2</sub>CF<sub>3</sub> | |
1-48 | H | OMe | H | H | CF<sub>2</sub>CF<sub>3</sub> | |
1-49 | H | NH<sub>2</sub> | H | H | CF<sub>2</sub>CF<sub>3</sub> | |
1-50 | H | NMe<sub>2</sub> | H | H | CF<sub>2</sub>CF<sub>3</sub> | |
1-51 | H | NHAc | H | H | CF<sub>2</sub>CF<sub>3</sub> | |
1-52 | H | SMe | H | H | CF<sub>2</sub>CF<sub>3</sub> | |
1-53 | H | SCF<sub>3</sub> | H | H | CF<sub>2</sub>CF<sub>3</sub> |
[表3]
第3表
化合物编号 | R<sup>1</sup> | R<sup>2</sup> | R<sup>3</sup> | R<sup>4</sup> | R<sup>5</sup> | 物性值 |
1-54 | H | CHO | H | H | CF<sub>2</sub>CF<sub>3</sub> | |
1-55 | H | CO<sub>2</sub>Et | H | H | CF<sub>2</sub>CF<sub>3</sub> | |
1-56 | H | CONHMe | H | H | CF<sub>2</sub>CF<sub>3</sub> | |
1-57 | H | CH=NOEt | H | H | CF<sub>2</sub>CF<sub>3</sub> | |
1-58 | H | c-Pr | H | H | CF<sub>2</sub>CF<sub>3</sub> | |
1-59 | H | H | F | H | CF<sub>2</sub>CF<sub>3</sub> | |
1-60 | H | H | Cl | H | CF<sub>2</sub>CF<sub>3</sub> | 193-194 |
1-61 | H | H | Br | H | CF<sub>2</sub>CF<sub>3</sub> | |
1-62 | H | H | I | H | CF<sub>2</sub>CF<sub>3</sub> | |
1-63 | H | H | CF<sub>3</sub> | H | CF<sub>2</sub>CF<sub>3</sub> | |
1-64 | H | H | CN | H | CF<sub>2</sub>CF<sub>3</sub> | |
1-65 | H | H | Me | H | CF<sub>2</sub>CF<sub>3</sub> | |
1-66 | H | H | OMe | H | CF<sub>2</sub>CF<sub>3</sub> | |
1-67 | H | H | NH<sub>2</sub> | H | CF<sub>2</sub>CF<sub>3</sub> | |
1-68 | H | H | NMe<sub>2</sub> | H | CF<sub>2</sub>CF<sub>3</sub> | |
1-69 | H | H | NHAc | H | CF<sub>2</sub>CF<sub>3</sub> | |
1-70 | H | H | SMe | H | CF<sub>2</sub>CF<sub>3</sub> | |
1-71 | H | H | SCF<sub>3</sub> | H | CF<sub>2</sub>CF<sub>3</sub> | |
1-72 | H | H | CHO | H | CF<sub>2</sub>CF<sub>3</sub> | |
1-73 | H | H | CO<sub>2</sub>Et | H | CF<sub>2</sub>CF<sub>3</sub> | |
1-74 | H | H | CONHMe | H | CF<sub>2</sub>CF<sub>3</sub> | |
1-75 | H | H | CH=NOEt | H | CF<sub>2</sub>CF<sub>3</sub> | |
1-76 | H | H | c-Pr | H | CF<sub>2</sub>CF<sub>3</sub> | |
1-77 | Cl | H | H | H | CF<sub>2</sub>CF<sub>3</sub> | 158-160 |
1-78 | H | H | H | Cl | CF<sub>2</sub>CF<sub>3</sub> | 158-161 |
[化学式6]
[表4]
第4表
化合物编号 | R<sup>1</sup> | R<sup>2</sup> | R<sup>3</sup> | R<sup>4</sup> | R<sup>5</sup> | 物性值 |
2-1 | H | H | H | H | CF<sub>3</sub> | 156-158 |
2-2 | H | F | H | H | CF<sub>3</sub> | |
2-3 | H | Cl | H | H | CF<sub>3</sub> | 183-185 |
2-4 | H | Br | H | H | CF<sub>3</sub> | 201-203 |
2-5 | H | I | H | H | CF<sub>3</sub> | 210-213 |
2-6 | H | CF<sub>3</sub> | H | H | CF<sub>3</sub> | 207-211 |
2-7 | H | CN | H | H | CF<sub>3</sub> | |
2-8 | H | Me | H | H | CF<sub>3</sub> | |
2-9 | H | OMe | H | H | CF<sub>3</sub> | |
2-10 | H | NH<sub>2</sub> | H | H | CF<sub>3</sub> | |
2-11 | H | NMe<sub>2</sub> | H | H | CF<sub>3</sub> | |
2-12 | H | NHAc | H | H | CF<sub>3</sub> | |
2-13 | H | SMe | H | H | CF<sub>3</sub> | |
2-14 | H | SCF<sub>3</sub> | H | H | CF<sub>3</sub> | |
2-15 | H | CHO | H | H | CF<sub>3</sub> | |
2-16 | H | CO<sub>2</sub>Et | H | H | CF<sub>3</sub> | |
2-17 | H | CONHMe | H | H | CF<sub>3</sub> | |
2-18 | H | CH=NOEt | H | H | CF<sub>3</sub> | |
2-19 | H | c-Pr | H | H | CF<sub>3</sub> | |
2-20 | H | H | F | H | CF<sub>3</sub> |
[表5]
第5表
化合物编号 | R<sup>1</sup> | R<sup>2</sup> | R<sup>3</sup> | R<sup>4</sup> | R<sup>5</sup> | 物性值 |
2-21 | H | H | Cl | H | CF<sub>3</sub> | 210-213 |
2-22 | H | H | Br | H | CF<sub>3</sub> | |
2-23 | H | H | I | H | CF<sub>3</sub> | |
2-24 | H | H | CF<sub>3</sub> | H | CF<sub>3</sub> | |
2-25 | H | H | CN | H | CF<sub>3</sub> | |
2-26 | H | H | Me | H | CF<sub>3</sub> | |
2-27 | H | H | OMe | H | CF<sub>3</sub> | |
2-28 | H | H | NH<sub>2</sub> | H | CF<sub>3</sub> | |
2-29 | H | H | NMe<sub>2</sub> | H | CF<sub>3</sub> | |
2-30 | H | H | NHAc | H | CF<sub>3</sub> | |
2-31 | H | H | SMe | H | CF<sub>3</sub> | |
2-32 | H | H | SCF<sub>3</sub> | H | CF<sub>3</sub> | |
2-33 | H | H | CHO | H | CF<sub>3</sub> | |
2-34 | H | H | CO<sub>2</sub>Et | H | CF<sub>3</sub> | |
2-35 | H | H | CONHMe | H | CF<sub>3</sub> | |
2-36 | H | H | CH=NOEt | H | CF<sub>3</sub> | |
2-37 | H | H | c-Pr | H | CF<sub>3</sub> | |
2-38 | Cl | H | H | H | CF<sub>3</sub> | |
2-39 | H | H | H | Cl | CF<sub>3</sub> | |
2-40 | H | OCF<sub>3</sub> | H | H | CF3 | 197-199 |
[化学式7]
[表6]
第6表
化合物编号 | R<sup>1</sup> | R<sup>2</sup> | R<sup>3</sup> | R<sup>4</sup> | R<sup>5</sup> | 物性值 |
3-1 | H | H | H | H | SCF<sub>3</sub> | 127 |
3-2 | H | F | H | H | SCF<sub>3</sub> | |
3-3 | H | Cl | H | H | SCF<sub>3</sub> | 111-113 |
3-4 | H | Br | H | H | SCF<sub>3</sub> | 110-111 |
3-5 | H | I | H | H | SCF<sub>3</sub> | 136 |
3-6 | H | CF<sub>3</sub> | H | H | SCF<sub>3</sub> | NMR |
3-7 | H | CN | H | H | SCF<sub>3</sub> | |
3-8 | H | Me | H | H | SCF<sub>3</sub> | |
3-9 | H | OMe | H | H | SCF<sub>3</sub> | |
3-10 | H | NH<sub>2</sub> | H | H | SCF<sub>3</sub> | |
3-11 | H | NMe<sub>2</sub> | H | H | SCF<sub>3</sub> | |
3-12 | H | NHAc | H | H | SCF<sub>3</sub> | |
3-13 | H | SMe | H | H | SCF<sub>3</sub> | |
3-14 | H | SCF<sub>3</sub> | H | H | SCF<sub>3</sub> | |
3-15 | H | CHO | H | H | SCF<sub>3</sub> | |
3-16 | H | CO<sub>2</sub>Et | H | H | SCF<sub>3</sub> | |
3-17 | H | CONHMe | H | H | SCF<sub>3</sub> | |
3-18 | H | CH=NOEt | H | H | SCF<sub>3</sub> | |
3-19 | H | c-Pr | H | H | SCF<sub>3</sub> | NMR |
3-20 | H | H | F | H | SCF<sub>3</sub> | |
3-21 | H | H | Cl | H | SCF<sub>3</sub> | 149-151 |
3-22 | H | H | Br | H | SCF<sub>3</sub> | |
3-23 | H | H | I | H | SCF<sub>3</sub> | |
3-24 | H | H | CF<sub>3</sub> | H | SCF<sub>3</sub> | |
3-25 | H | H | CN | H | SCF<sub>3</sub> | |
3-26 | H | H | Me | H | SCF<sub>3</sub> |
[表7]
第7表
化合物编号 | R<sup>1</sup> | R<sup>2</sup> | R<sup>3</sup> | R<sup>4</sup> | R<sup>5</sup> | 物性值 |
3-27 | H | H | OMe | H | SCF<sub>3</sub> | |
3-28 | H | H | NH<sub>2</sub> | H | SCF<sub>3</sub> | |
3-29 | H | H | NMe<sub>2</sub> | H | SCF<sub>3</sub> | |
3-30 | H | H | NHAc | H | SCF<sub>3</sub> | |
3-31 | H | H | SMe | H | SCF<sub>3</sub> | |
3-32 | H | H | SCF<sub>3</sub> | H | SCF<sub>3</sub> | |
3-33 | H | H | CHO | H | SCF<sub>3</sub> | |
3-34 | H | H | CO<sub>2</sub>Et | H | SCF<sub>3</sub> | |
3-35 | H | H | CONHMe | H | SCF<sub>3</sub> | |
3-36 | H | H | CH=NOEt | H | SCF<sub>3</sub> | |
3-37 | H | H | c-Pr | H | SCF<sub>3</sub> | |
3-38 | Cl | H | H | H | SCF<sub>3</sub> | |
3-39 | H | H | H | Cl | SCF<sub>3</sub> | |
3-40 | H | H | H | H | SO<sub>2</sub>CF<sub>3</sub> | |
3-41 | H | F | H | H | SO<sub>2</sub>CF<sub>3</sub> | |
3-42 | H | Cl | H | H | SO<sub>2</sub>CF<sub>3</sub> | |
3-43 | H | Br | H | H | SO<sub>2</sub>CF<sub>3</sub> | |
3-44 | H | I | H | H | SO<sub>2</sub>CF<sub>3</sub> | |
3-45 | H | CF<sub>3</sub> | H | H | SO<sub>2</sub>CF<sub>3</sub> | NMR |
3-46 | H | CN | H | H | SO<sub>2</sub>CF<sub>3</sub> | |
3-47 | H | Me | H | H | SO<sub>2</sub>CF<sub>3</sub> | |
3-48 | H | OMe | H | H | SO<sub>2</sub>CF<sub>3</sub> | |
3-49 | H | NH<sub>2</sub> | H | H | S0<sub>2</sub>CF<sub>3</sub> | |
3-50 | H | NMe<sub>2</sub> | H | H | SO<sub>2</sub>CF<sub>3</sub> | |
3-51 | H | NHAc | H | H | SO<sub>2</sub>CF<sub>3</sub> | |
3-52 | H | SMe | H | H | SO<sub>2</sub>CF<sub>3</sub> |
[表8]
第8表
化合物编号 | R<sup>1</sup> | R<sup>2</sup> | R<sup>3</sup> | R<sup>4</sup> | R<sup>5</sup> | 物性值 |
3-53 | H | SCF<sub>3</sub> | H | H | SO<sub>2</sub>CF<sub>3</sub> | |
3-54 | H | CHO | H | H | SO<sub>2</sub>CF<sub>3</sub> | |
3-55 | H | CO<sub>2</sub>Et | H | H | SO<sub>2</sub>CF<sub>3</sub> | |
3-56 | H | CONHMe | H | H | SO<sub>2</sub>CF<sub>3</sub> | |
3-57 | H | CH=NOEt | H | H | SO<sub>2</sub>CF<sub>3</sub> | |
3-58 | H | c-Pr | H | H | SO<sub>2</sub>CF<sub>3</sub> | |
3-59 | H | H | F | H | SO<sub>2</sub>CF<sub>3</sub> | |
3-60 | H | H | Cl | H | SO<sub>2</sub>CF<sub>3</sub> | |
3-61 | H | H | Br | H | SO<sub>2</sub>CF<sub>3</sub> | |
3-62 | H | H | I | H | SO<sub>2</sub>CF<sub>3</sub> | |
3-63 | H | H | CF<sub>3</sub> | H | SO<sub>2</sub>CF<sub>3</sub> | |
3-64 | H | H | CN | H | SO<sub>2</sub>CF<sub>3</sub> | |
3-65 | H | H | Me | H | SO<sub>2</sub>CF<sub>3</sub> | |
3-66 | H | H | OMe | H | SO<sub>2</sub>CF<sub>3</sub> | |
3-67 | H | H | NH<sub>2</sub> | H | SO<sub>2</sub>CF<sub>3</sub> | |
3-68 | H | H | NMe<sub>2</sub> | H | SO<sub>2</sub>CF<sub>3</sub> | |
3-69 | H | H | NHAc | H | SO<sub>2</sub>CF<sub>3</sub> | |
3-70 | H | H | SMe | H | SO<sub>2</sub>CF<sub>3</sub> | |
3-71 | H | H | SCF<sub>3</sub> | H | SO<sub>2</sub>CF<sub>3</sub> | |
3-72 | H | H | CHO | H | SO<sub>2</sub>CF<sub>3</sub> | |
3-73 | H | H | CO<sub>2</sub>Et | H | SO<sub>2</sub>CF<sub>3</sub> | |
3-74 | H | H | CONHMe | H | SO<sub>2</sub>CF<sub>3</sub> | |
3-75 | H | H | CH=NOEt | H | SO<sub>2</sub>CF<sub>3</sub> | |
3-76 | H | H | c-Pr | H | SO<sub>2</sub>CF<sub>3</sub> | |
3-77 | Cl | H | H | H | SO<sub>2</sub>CF<sub>3</sub> | |
3-78 | H | H | H | Cl | SO<sub>2</sub>CF<sub>3</sub> | |
3-79 | H | Cl | Cl | H | SCF<sub>3</sub> | NMR |
3-80 | H | CF<sub>3</sub> | H | H | SOCF<sub>3</sub> | NMR |
3-81 | H | Cl | Cl | H | SOCF<sub>3</sub> | NMR |
3-82 | H | Cl | Cl | H | SO<sub>2</sub>CF<sub>3</sub> | NMR |
3-83 | H | I | Cl | H | SCF<sub>3</sub> | 128-131 |
3-84 | Cl | H | H | H | SCF<sub>3</sub> | 120-122 |
3-85 | Cl | Cl | H | H | SCF<sub>3</sub> | 120-122 |
[化学式8]
[表9]
第9表
化合物编号 | R<sup>1</sup> | R<sup>2</sup> | R<sup>3</sup> | R<sup>4</sup> | R<sup>5</sup> | 物性值 |
4-1 | H | H | H | H | CF<sub>3</sub> | |
4-2 | H | Cl | H | H | CF<sub>3</sub> | |
4-3 | H | H | Cl | H | CF<sub>3</sub> | |
4-4 | H | CF<sub>3</sub> | H | H | CF<sub>3</sub> | |
4-5 | H | H | CF<sub>3</sub> | H | CF<sub>3</sub> | |
4-6 | H | c-Pr | H | H | CF<sub>3</sub> | |
4-7 | H | Br | H | H | CF<sub>3</sub> | |
4-8 | H | I | H | H | CF<sub>3</sub> | |
4-9 | H | H | Cl | H | SCF<sub>3</sub> | 214-215 |
4-10 | H | H | Cl | H | SOCF<sub>3</sub> | 206-208 |
4-11 | H | H | Cl | H | SO<sub>2</sub>CF<sub>3</sub> | 190-192 |
4-12 | H | Cl | Cl | H | SCF<sub>3</sub> | 242-244 |
4-13 | H | Cl | Cl | H | SOCF<sub>3</sub> | 256-258 |
4-14 | H | Cl | Cl | H | SO<sub>2</sub>CF<sub>3</sub> | 215-217 |
[化学式9]
[表10]
第10表
化合物编号 | R<sup>1</sup> | R<sup>2</sup> | R<sup>3</sup> | R<sup>4</sup> | R<sup>5</sup> | 物性值 |
5-1 | H | H | H | H | CF<sub>3</sub> | |
5-2 | H | Cl | H | H | CF<sub>3</sub> | |
5-3 | H | H | Cl | H | CF<sub>3</sub> | |
5-4 | H | CF<sub>3</sub> | H | H | CF<sub>3</sub> | |
5-5 | H | H | CF<sub>3</sub> | H | CF<sub>3</sub> | |
5-6 | H | c-Pr | H | H | CF<sub>3</sub> | |
5-7 | H | Br | H | H | CF<sub>3</sub> | |
5-8 | H | I | H | H | CF<sub>3</sub> |
[表11]
第11表1H-NMR数据
含有本发明的通式(1)所表示的吲哚啉化合物或其盐类作为有效成分的农业园艺用杀虫剂,适用于加害水稻、果树、蔬菜、其他作物及花卉类的各种农林、园艺、贮粮害虫或卫生害虫、或者线虫类等害虫的防除。
作为上述害虫或线虫类等可例示出以下虫类。
作为鳞翅目(Lepidoptera)害虫,例如可列举出绿刺蛾(Parasa consocia)、桥夜蛾(Anomis mesogona)、柑橘凤蝶(Papilio xuthus)、日豆小卷蛾(Matsumuraesesazukivora)、麻田豆秆野螟(Ostrinia scapulalis)、莎草粘虫(Spodoptera exempta)、美国白蛾(Hyphantria cunea)、亚洲玉米螟(Ostrinia furnacalis)、东方粘虫(Pseudaletiaseparata)、衣蛾(Tinea translucens)、尖翅小卷蛾(Bactra furfuryla)、直纹稻弄蝶(Parnara guttata)、稻显纹刷须野螟(Marasmia exigua)、直纹稻弄蝶(Parnaraguttata)、大螟(Sesamia inferens)、甘薯麦蛾(Brachmia triannulella)、黄刺蛾(Monemaflavescens)、粉斑夜蛾(Trichoplusia ni)、苧麻肋野螟蛾(Pleuroptya ruralis)、小蜻蜓尺蛾(Cystidia couaggaria)、亮灰蝶(Lampides boeticus)、咖啡透翅天蛾(Cephonodeshylas)、棉铃虫(Helicoverpa armigera)、曼蚕舟蛾(Phalerodonta manleyi)、大避债蛾(Eumeta japonica)、欧洲粉蝶(Pieris brassicae)、天幕毛虫(Malacosoma neustriatestacea)、柿举肢蛾(Stathmopoda masinissa)、柿细蛾(Cuphodes diospyrosella)、梣黄卷蛾(Archips xylosteanus)、黄地老虎(Agrotis segetum)、甘蔗黄螟(Tetramoeraschistaceana)、黄凤蝶(Papilio machaon hippocrates)、黄斑蝙蝠蛾(Endoclytasinensis)、银纹潜叶蛾(Lyonetia prunifoliella)、金纹小潜细蛾(Phyllonorycterringoneella)、栗白小卷蛾(Cydia kurokoi)、栗绿小卷蛾(Eucoenogenes aestuosa)、葡萄花翅小卷蛾(Lobesia botrana)、中国绿刺蛾(Latoia sinica)、皮暗斑螟(Euzopherabatangensis)、慈菇褐纹卷蛾(Phalonidia mesotypa)、桑斑雪灯蛾(Spilosomaimparilis)、桑绢野螟(Glyphodes pyloalis)、桑卷叶蛾(Olethreutes mori)、幕谷蛾(Tineola bisselliella)、蝙蝠蛾(Endoclyta excrescens)、谷蛾(Nemapogongranellus)、苹果透翅蛾(Synanthedon hector)、苹果小卷蛾(Cydia pomonella)、小菜蛾(Plutella xylostella)、稻纵卷叶野螟(Cnaphalocrocis medinalis)、蛀茎夜蛾(Sesamiacalamistis)、三化螟(Scirpophaga incertulas)、兰草螟蛾(Pediasia teterrellus)、马铃薯块茎蛾(Phthorimaea operculella)、苹蚁舟蛾(Stauropus fagi persimilis)、豆荚螟(Etiella zinckenella)、甜菜夜蛾(Spodoptera exigua)、白斑蝙蝠蛾(Palpifersexnotata)、灰翅夜蛾(Spodoptera mauritia)、稻白螟(Scirpophaga innotata)、八字地老虎(Xestia c-nigrum)、淡剑纹灰翅夜蛾(Spodoptera depravata)、地中海斑螟(Ephestia kuehniella)、李尺蛾(Angerona prunaria)、分月扇舟蛾(Closteraanastomosis)、大豆夜蛾(Pseudoplusia includens)、松村氏捲蛾(Matsumuraesesfalcana)、烟实夜蛾(Helicoverpa assulta)、黑点丫纹夜蛾(Autographa nigrisigna)、球菜夜蛾(Agrotis ipsilon)、茶黄毒蛾(Euproctis pseudoconspersa)、棉褐带卷蛾(Adoxophyes orana)、茶细蛾(Caloptilia theivora)、茶长卷蛾(Homona magnanima)、烟草粉斑螟(Ephestia elutella)、茶避债蛾(Eumeta minuscula)、杨扇舟蛾(Closteraanachoreta)、亚麻夜蛾(Heliothis maritima)、葡萄长须卷蛾(Sparganothispilleriana)、亚澳白裙夜蛾(Busseola fusca)、东方毒蛾(Euproctis subflava)、褐纹大尺蛾(Biston robustum)、玉米夜蛾(Heliothis zea)、甘薯烦夜蛾(Aedia leucomelas)、梨娜刺蛾(Narosoideus flavidorsalis)、梨剑纹夜蛾(Viminia rumicis)、梨角折蛾(Bucculatrix pyrivorella)、梨小食心虫(Grapholita molesta)、梨潜皮细蛾(Spulerinaastaurota)、果外髓斑螟(Ectomyelois pyrivorella)、二化螟(Chilo suppressalis)、葱菜蛾(Acrolepiopsis sapporensis)、印度谷螟(Plodia interpunctella)、菜心野螟(Hellula undalis)、麦蛾(Sitotroga cerealella)、斜纹夜蛾(Spodoptera litura)、绿豆芽蛾的一种(Eucosma aporema)、草莓长翅卷蛾(Acleris comariana)、灰齿刺蛾(Scopelodes contractus)、旋古毒蛾(Orgyia thyellina)、草地夜蛾(Spodopterafrugiperda)、Ostrinia zaguliaevi、双带夜蛾(Naranga aenescens)、茶蚕蛾(Andracabipunctata)、葡萄透翅蛾(Paranthrene regalis)、缺角天蛾(Acosmeryx castanea)、葡萄潜叶蛾(Phyllocnistis toparcha)、葡萄浆果蛾(Endopiza viteana)、环针单纹蛾(Eupoecillia ambiguella)、黎豆夜蛾(Anticarsia gemmatalis)、Cnephasiacinereipalpana、舞毒蛾(Lymantria dispar)、赤松毛虫(Dendrolimus spectabilis)、大豆食心虫(Leguminivora glycinivorella)、豆荚野螟(Maruca testulalis)、豆小卷蛾(Matsumuraeses phaseoli)、大豆丽细蛾(Caloptilia soyella)、柑桔叶潜蛾(Phyllocnistis citrella)、豆啮叶野螟(Omiodes indicate)、杏黄卷蛾(Archipsfuscocupreanus)、银纹夜蛾(Acanthoplusia agnata)、桑蓑蛾(Bambalina sp.)、桃蛀果蛾(Carposina niponensis)、桃蛀螟(Conogethes punctiferalis)、樟兴透翅蛾(Synanthedon sp.)、桃潜蛾(Lyonetia clerkella)、小黄斑粉蝶(Papilio helenus)、斑缘豆粉蝶(Colias erate poliographus)、苹掌舟蛾(Phalera flavescens)、小菜粉蝶日本亚种(Pieris rapae crucivora)、菜粉蝶(Pieris rapae)等粉蝶类、桑毛虫(Euproctissimilis)、点线锦织蛾(Acrolepiopsis suzukiella)、欧洲玉米螟(Ostrinia nubilalis)、甘蓝夜蛾(Mamestra brassicae)、大造桥虫(Ascotis selenaria)、艾草大细卷叶蛾(Phtheochroides clandestina)、北川卷蛾(Hoshinoa adumbratana)、圆斑黄枯叶蝶(Odonestis pruni japonensis)、苹剑纹夜蛾(Triaena intermedia)、苹小卷叶蛾(Adoxophyes orana fasciata)、苹小食心虫(Grapholita inopinata)、苹白小卷蛾(Spilonota ocellana)、顶梢卷叶蛾(Spilonota lechriaspis)、梨星毛虫(Illiberispruni)、苹果银蛾(Argyresthia conjugella)、猛花细蛾(Caloptilia zachrysa)、梨黄卷蛾(Archips breviplicanus)、小造桥夜蛾(Anomis flava)、棉红铃虫(Pectinophoragossypiella)、棉大卷叶野螟(Notarcha derogata)、瓜绢野螟(Diaphania indica)、烟芽夜蛾(Heliothis virescens)及鼎点钻夜蛾(Eariascupreoviridis)等。
作为半翅目(Hemiptera)害虫,例如可列举出稻绿椿(Nezara antennata)、赤条纤盲蝽(Stenotus rubrovittatus)、黑条红椿象(Graphosoma rubrolineatum)、条赤须盲蝽(Trigonotylus coelestialium)等、黄伊缘蝽(Aeschynteles maculatus)、Creontiadespallidifer、赤星椿象(Dysdercus cingulatus)、褐圆介壳虫(Chrysomphalus ficus)、肾圆盾蚧(Aonidiella aurantii)、油蝉(Graptopsaltria nigrofuscata)、麦长蝽(Blissusleucopterus)、吹绵蚧(Icerya purchasi)、壁椿(Piezodorus hybneri)、稻褐蝽(Lagynotomus elongatus)、白翅叶蝉(Thaia subrufa)、稻黑蝽(Scotinophara lurida)、玫瑰蚜(Sitobion ibarae)、Stariodes iwasakii、椰圆盾蚧(Aspidiotus destructor)、苍白泰盲蝽(Taylorilygus pallidulus)、杏瘤蚜(Myzus mumecola)、梅白蚧(Pseudaulacaspis prunicola)、豌豆蚜(Acyrthosiphon pisum)、纹须同缘椿象(Anacanthocoris striicornis)、跃盲蝽(Ectometopterus micantulus)、日本二星棒(Eysarcoris lewisi)、巨叶足虫(Molipteryx fuliginosa)、大青叶蝉(Cicadellaviridis)、红腹缢管蚜(Rhopalosophum rufiabdominalis)、黑蜡蚧(Saissetia oleate)、温室粉虱(Trialeurodes vaporariorum)、橡木叶蝉(Aguriahana quercus)、草盲蝽属(Lygus spp.)、桦绵斑蚜(Euceraphis punctipennis)、柑橘介壳虫(Andaspiskashicola)、橘软蜡蚧(Coccus pseudomagnoliarum)、甘蔗异背长蝽(Caveleriussaccharivorus)、菊贝脊网蝽(Galeatus spinifrons)、菊小长管蚜(Macrosiphoniellasanborni)、黄圆蹄盾蚧(Aonidiella citrina)、茶翅蝽(Halyomorpha mista)、樟网蝽(Stephanitis fasciicarina)、樟木虱(Trioza camphorae)、中稻缘蝽(Leptocorisachinensis)、Trioza quercicola、黄角肩网蝽(Uhlerites latius)、葡萄伴斑叶蝉(Erythroneura comes)、长蝽(Paromius exiguus)、柘柳重圆盾蚧(Duplaspidiotusclaviger)、二条斑黑尾叶蝉(Nephotettix nigropictus)、庭园盲蝽(Halticiellusinsularis)、甘蔗扁角飞虱(Perkinsiella saccharicida)、苹果木虱(Psyllamalivorella)、桑木虱(Anomomeura mori)、长尾粉蚧(Pseudococcus longispinis)、桑白盾蚧(Pseudaulacaspis pentagona)、桑绵蜡蚧(Pulvinaria kuwacola)、绿盲蝽(Apolyguslucorum)、葫芦长蝽(Togo hemipterus)、桔二叉蚜(Toxoptera aurantii)、糖粉蚧(Saccharicoccus sacchari)、蔗根蚜(Geoica lucifuga)、瓶额飞虱(Numata muiri)、梨圆介壳虫(Comstockaspis perniciosa)、桔矢尖盾蚧(Unaspis citri)、茄沟无网蚜(Aulacorthum solani)、广二星蝽(Eysarcoris ventralis)、银叶粉虱(Bemisiaargentifolii)、大白叶蝉(Cicadella spectra)、春藤圆盾蚧(Aspidiotus hederae)、粟缘蝽(Liorhyssus hyalinus)、黑背丽木虱(Calophya nigridorsalis)、白背稻虱(Sogatella furcifera)、空豆髭长油虫(Megoura crassicauda)、甘蓝蚜(Brevicorynebrassicae)、大豆蚜(Aphis glycines)、稻斑腹蛛缘蝽(Leptocorisa oratorius)、二点黑尾叶蝉(Nephotettix virescens)、莴苣指管蚜(Uroeucon formosanum)、烟盲蝽(Cyrtopeltis tennuis)、烟粉虱(Bemisia tabaci)、桃蜡蚧(Lecanium persicae)、茶糠蚧(Parlatoria theae)、牡丹网纹盾蚧(Pseudaonidia paeoniae)、大贯小绿叶蝉(Empoascaonukii)、褐翅绿椿象(Plautia stali)、百合西圆尾蚜(Dysaphis tulipae)、大戟长管蚜(Macrosiphum euphorbiae)、杜鹃冠网蝽(Stephanitis pyrioides)、角蜡蚧(Ceroplastesceriferus)、山茶糠蚧(Parlatoria camelliae)、淡娇异蝽(Apolygus spinolai)、黑尾叶蝉(Nephotettix cincticeps)、青蝽(Glaucias subpunctatus)、杂毛合垫盲蝽(Orthotylus flavosparsus)、玉米蚜(Rhopalosiphum maidis)、玉米蜡蝉(Peregrinusmaidis)、二星蝽(Eysarcoris parvus)、温带臭虫(Cimex lectularius)、冷杉木虱(Psyllaabieti)、褐飞虱(Nilaparvata lugens)、海桐木虱(Psylla tobirae)、皱纹菜蝽(Eurydemarugosum)、梨二叉蚜(Schizaphis piricola)、梨黄木虱(Psylla pyricola)、梨星片盾蚧(Parlatoreopsis pyri)、梨冠网蝽(Stephanitis nashi)、水松粉蚧(Dysmicoccuswistariae)、梨蚧(Lepholeucaspis japonica)、梨园尾蚜(Sappaphis piri)、萝卜蚜(Lipaphis erysimi)、台湾韭蚜(Neotoxoptera formosana)、莲缢管蚜(Rhopalosophumnymphaeae)、蔷薇小叶蝉(Edwardsianarosae)、苏铁褐点盾蚧(Pinnaspis aspidistrae)、赤杨木虱(Psylla alni)、叶蝉(Speusotettix subfusculus)、杂食性叶蝉(Alnetoidiaalneti)、稗飞虱(Sogatella panicicola)、苜蓿盲蝽(Adelphocoris lineolatus)、联斑棉红蝽(Dysdercus poecilus)、黑片盾蚧(Parlatoria ziziphi)、褐角肩网蝽(Uhleritesdebile)、灰飞虱(Laodelphax striatellus)、六斑菜蝽(Eurydema pulchrum)、长肩棘缘椿象(Cletus trigonus)、一点铲头沫蝉(Clovia punctata)、小绿叶蝉(Empoasca sp.)、褐软蜡蚧(Coccus hesperidum)、草鼓胸长蝽(Pachybrachius luridus)、藤臀纹粉蚧(Planococcus kraunhiae)、双斑盲蝽(Stenotus binotatus)、葡萄阿小叶蝉(Arboridiaapicalis)、二点叶蝉(Macrosteles fascifrons)、斑须蝽(Dolycoris baccarum)、三环苜蓿盲蝽(Adelphocoris triannulatus)、葡萄根瘤蚜(Viteus vitifolii)、瘤缘椿象(Acanthocoris sordidus)、大稻缘蝽(Leptocorisa acuta)、瘤腹巨股长蝽(Macropesobnubilus)、稻棘缘蝽(Cletus punctiger)、点蜂缘椿象(Riptortus clavatus)、番茄木虱(Paratrioza cockerelli)、柳尖胸沫蝉(Aphrophora costalis)、日本草盲蝽(Lygusdisponsi)、东亚草盲蝽(Lygus saundersi)、松白粉蚧(Crisicoccus pini)、松小叶蝉(Empoasca abietis)、松粉蚧(Crisicoccus matsumotoi)、豆蚜(Aphis craccivora)、臭蝽(Megacopta punctatissimum)、圆白星椿象(Eysarcoris guttiger)、紫疤蛎盾蚧(Lepidosaphes beckii)、柑桔木虱(Diaphorina citri)、桔蚜(Toxoptera citricidus)、柑桔粉蚧(Planococcus citri)、柑橘粉虱(Dialeurodes citri)、黑刺粉虱(Aleurocanthus spiniferus)、柑橘小粉蚧(Pseudococcus citriculus)、Zyginellacitri、桔绵蜡蚧(Pulvinaria citricola)、偏软蜡蚧(Coccus discrepans)、蛇眼臀网盾蚧(Pseudaonidia duplex)、柑橘绵蚧(Pulvinaria aurantii)、东方球蜡蚧(Lecaniumcorni)、稻绿蝽(Nezara viridula)、二刺狭盲蝽(Stenodema calcaratum)、禾谷缢管蚜(Rhopalosiphum padi)、麦长管蚜(Sitobion akebiae)、麦二叉蚜(Schizaphisgraminum)、Sorhoanus tritici、光管舌尾蚜(Brachycaudus helichrysi)、紫翅果蝽(Carpocoris purpureipennis)、桃蚜(Myzus persicae)、桃大尾蚜(Hyalopterus pruni)、柳蚜(Aphis farinose yanagicola)、杨柳网蝽(Metasalis populi)、矢尖盾蚧(Unaspisyanonensis)、芙蓉木虱(Mesohomotoma camphorae)、绣线菊蚜(Aphis spiraecola)、苹果蚜(Aphis pomi)、榆蛎盾蚧(Lepidosaphes ulmi)、苹木虱(Psylla mali)、苹叶盲蝽(Heterocordylus flavipes)、苹果瘤蚜(Myzus malisuctus)、苹果蚜虫(Aphidonuguismali)、苹果叶蝉(Orientus ishidai)、苹果蚜(Ovatus malicolens)、苹绵蚜(Eriosomalanigerum)、红蜡蚧(Ceroplastes rubens)及棉蚜(Aphis gossypii)等。
作为鞘翅目(Coleoptera)害虫,例如可列举出合欢双条天牛(Xystroceraglobosa)、毒隐翅虫(Paederus fuscipes)、金边青花金龟(Eucetonia roelofsi)、绿豆象(Callosobruchus chinensis)、甘薯小象(Cylas formicarius)、紫苜蓿叶象(Hyperapostica)、稻象甲(Echinocnemus squameus)、水稻负泥虫(Oulema oryzae)、水稻负泥虫(Oulema oryzae)、长腿水叶甲(Donacia provosti)、稻水象甲(Lissorhoptrusoryzophilus)、甘薯叶甲(Colasposoma dauricum)、西印度甘薯象甲(Euscepespostfasciatus)、墨西哥豆瓢虫(Epilachna varivestis)、菜豆象(Acanthoscelidesobtectus)、玉米根叶甲(Diabrotica virgifera virgifera)、李蓝卷象(Involvuluscupreus)、黄守瓜(Aulacophora femoralis)、豌豆象(Bruchus pisorum)、马铃薯瓢虫(Epilachna vigintioctomaculata)、脊胸露尾甲(Carpophilus dimidiatus)、甜菜大龟甲(Cassida nebulosa)、粗背寡毛跳甲(Luperomorpha tunebrosa)、黄曲条菜跳甲(Phyllotreta striolata)、黄星天牛(Psacothea hilaris)、黄斑天牛(Aeolestheschrysothrix)、蒙栎象(Curculio sikkimensis)、酱曲露尾甲(Carpophilus hemipterus)、小青花金龟(Oxycetonia jucunda)、根萤叶甲(Diabrotica spp.)、亮绿彩丽金龟(Mimelasplendens)、玉米象(Sitophilus zeamais)、赤拟谷盗(Tribolium castaneum)、米象(Sitophilus oryzae)、亚扁粉盗(Palorus subdepressus)、日本豆金龟(Melolonthajaponica)、星天牛(Anoplophora malasiaca)、大点拟粉虫(Neatus picipes)、马铃薯叶甲(Leptinotarsa decemlineata)、黄瓜十一星叶甲食根亚种(Diabrotica undecimpunctatahowardi)、猎象(Sphenophorus venatus)、十四点负泥虫(Criocerisquatuordecimpunctata)、梅球颈象(Conotrachelus nenuphar)、大根猿象虫(Ceuthorhynchidius albosuturalis)、小猿叶虫(Phaedon brassicae)、烟草甲(Lasioderma serricorne)、日本根瘤象(Sitona japonicus)、斑喙丽金龟(Adoretustenuimaculatus)、面粉甲虫(Tenebrio molitor)、Basilepta balyi、小车轴草叶象甲(Hypera nigrirostris)、甜菜跳甲(Chaetocnema concinna)、大绿丽金龟(Anomalacuprea)、黑七鳃金龟(Heptophylla picea)、茄二十八星瓢虫(Epilachnavigintioctopunctata)、长角叶甲(Diabrotica longicornis)、Eucetonia pilifera、叩甲属(Agriotes spp.)、黑毛皮蠹(Attagenus unicolor japonicus)、斑鞘豆叶甲(Pagriasignata)、红铜丽金龟(Anomala rufocuprea)、姬帕谷甲(Palorus ratzeburgii)、褐菌虫(Alphitobius laevigatus)、地毯甲虫(Anthrenus verbasci)、褐粉蠹(Lyctusbrunneus)、杂拟谷盗(Tribolium confusum)、黑条麦萤叶甲(Medythia nigrobilineata)、葡萄脊虎天牛(Xylotrechus pyrrhoderus)、黄瓜跳甲(Epitrix cucumeris)、纵坑切梢小蠹(Tomicus piniperda)、松墨天牛(Monochamus alternatus)、日本弧丽金龟(Popilliajaponica)、豆芫青(Epicauta gorhami)、玉米象(Sitophilus zeamais)、日本苹虎象(Rhynchites heros)、蔬菜叶象甲(Listroderes costirostris)、四纹豆象(Callosobruchus maculatus)、苹霜绿切叶象(Phyllobius armatus)、苹果开花象鼻虫(Anthonomus pomorum)、铜绿里叶甲(Linaeidea aenea)及墨西哥棉铃象(Anthonomusgrandis)等。
作为双翅目(Diptera)害虫,例如可列举出淡色库蚊(Culex pipiens pallens)、甜菜潜叶蝇(Pegomya hyoscyami)、南美斑潜蝇(Liriomyza huidobrensis)、家蝇(Muscadomestica)、稻秆蝇(Chlorops oryzae)、稻心蝇(Hydrellia sasakii)、日本稻潜蝇(Agromyza oryzae)、姬稻潜叶蝇(Hydrellia griseola)、麦叶毛眼水蝇(Hydrelliagriseola)、菜豆蛇潜蝇(Ophiomyia phaseoli)、瓜实蝇(Dacus cucurbitae)、樱桃果蝇(Drosophila suzukii)、日本樱桃实蝇(Rhacochlaena japonica)、厩腐蝇(Muscinastabulans)、东亚异蚤蝇(Megaselia spiracularis)等蚤蝇科类、毛蠓(Clogmiaalbipunctata)、稻大蚊(Tipula aino)、伏蝇(Phormia regina)、三带喙库蚊(Culextritaeniorhynchus)、中华按蚊(Anopheles sinensis)、甘蓝地种蝇(Hylemyabrassicae)、大豆荚瘿蝇(Asphondylia sp.)、灰地种蝇(Delia platura)、葱地种蝇(Deliaantiqua)、樱桃绕实绳(Rhagoletis cerasi)、地下家蚊(Culex pipiens molestusForskal)、地中海实蝇(Ceratitis capitata)、黑翅蕈蝇(Bradysia agrestis)、肖藜泉蝇(Pegomya cunicularia)、美洲斑潜蝇(Liriomyza sativae)、番茄斑潜蝇(Liriomyzabryoniae)、豌豆彩潜蝇(Chromatomyia horticola)、葱斑潜蝇(Liriomyza chinensis)、致倦库蚊(Culex quinquefasciatus)、埃及伊蚊(Aedes aegypti)、白纹伊蚊(Aedesalbopictus)、三叶斑潜蝇(Liriomyza trifolii)、美洲斑潜蝇(Liriomyza sativae)、东方果实蝇(Dacus dorsalis)、蜜柑大实蝇(Dacus tsuneonis)、麦红吸浆虫(Sitodiplosismosellana)、黑腹麦秆蝇(Meromuza nigriventris)、墨西哥按实蝇(Anastrepha ludens)及苹果实蝇(Rhagoletis pomonella)等。
作为膜翅目(Hymenoptera)害虫,例如可列举出短刺棱胸切叶蚁(Pristomyrmexpungens)、肿腿蜂科类、法老蚁(Monomorium pharaohnis)、宽节大头蚁(Pheidole noda)、菜叶蜂(Athalia rosae)、栗瘿蜂(Dryocosmus kuriphilus)、日本黑褐蚁(Formica fuscajaponica)、胡蜂亚科类、黑背白萝卜叶蜂(Athalia infumata infumata)、月季叶蜂(Argepagana)、日本芜菁叶蜂(Athalia japonica)、切叶蚁(Acromyrmex spp.)、火蚁(Solenopsis spp.)、苹果三节叶蜂(Arge mali)及光滑管琉璃蚁(Ochetellus glaber)等。
作为直翅目(Acrididae)害虫,例如可列举出南方稻草螽(Homorocoryphuslineosus)、蝼蛄(Gryllotalpa sp.)、小稻蝗(Oxya hyla intricata)、小翅稻蝗(Oxyayezoensis)、飞蝗(Locusta migratoria)、短翅稻蝗(Oxya japonica)、北方水稻螽斯(Homorocoryphus jezoensis)及黄脸油葫芦(Teleogryllus emma)等。
作为缨翅目害虫,例如可列举出红带滑胸针蓟马(Selenothrips rubrocinctus)、稻蓟马(Stenchaetothrips biformis)、稻管蓟马(Haplothrips aculeatus)、Ponticulothrips diospyrosi、黄蓟马(Thrips flavus)、玉米黄呆蓟马(Anaphothripsobscurus)、佛州樟蓟马(Liothrips floridensis)、唐菖蒲简蓟马(Thrips simplex)、菊黑毛蓟马(Thrips nigropilosus)、温室蓟马(Heliothrips haemorrhoidalis)、桑蓟马(Pseudodendrothrips mori)、腹小头蓟马(Microcephalothrips abdominalis)、帕氏毛管蓟马(Leeuwenia pasanii)、Litotetothrips pasaniae、柑桔硬蓟马(Scirtothripscitri)、华简管蓟马(Haplothrips chinensis)、豆喙蓟马(Mycterothrips glycines)、毛蓟马(Thrips setosus)、茶黄蓟马(Scirtothrips dorsalis)、茶棍蓟马(Dendrothripsminowai)、黑角简管蓟马(Haplothrips niger)、烟蓟马(Thrips tabaci)、葱蓟马(Thripsalliorum)、黄胸蓟马(Thrips hawaiiensis)、豆简管蓟马(Haplothrips kurdjumovi)、袖指蓟马(Chirothrips manicatus)、花蓟马(Frankliniella intonsa)、日本蓟马(Thripscoloratus)、西花蓟马(Franklinella occidentalis)、棕榈蓟马(Thrips palmi)、百合蓟马(Frankliniella lilivora)及百合滑管蓟马(Liothrips vaneeckei)等。
作为蜱螨目害虫,例如可列举出红纤沙螨(Leptotrombidium akamushi)、卢氏叶螨(Tetranychus ludeni)、变异革蜱(Dermacentor variabilis)、截形叶螨(Tetranychustruncatus)、柏氏禽刺螨(Ornithonyssus bacoti)、犬蠕形螨(Demodex canis)、山楂叶螨(Tetranychus viennensis)、神泽氏叶螨(Tetranychus kanzawai)、血红扇头蜱(Rhipicephalus sanguineus)等硬蜱科类、马六甲肉食螨(Cheyletus malaccensis)、腐食酪螨(Tyrophagus putrescentiae)、粉剂螨(Dermatophagoides farinae)、红背蜘蛛(Latrodectus hasseltii)、台湾革蜱(Dermacentor taiwanicus)、茶尖叶节蜱(Acaphyllatheavagrans)、侧多食跗线螨(Polyphagotarsonemus latus)、番茄刺皮瘿螨(Aculopslycopersici)、Ornithonyssus sylvairum、二斑叶螨(Tetranychus urticae)、中国瘿螨(Eriophyes chibaensis)、人疥螨(Sarcoptes scabiei)、长角血蜱(Haemaphysalislongicornis)、有胛硬蜱(Ixodes scapularis)、似食酪螨(Tyrophagus similis)、普通肉食螨(Cheyletus eruditus)、柑桔全爪螨(Panonychus citri)、莫氏肉食螨(Cheyletusmoorei)、紫红短须螨(Brevipalpus phoenicis)、犬猫耳螨(Octodectes cynotis)、欧洲室尘螨(Dermatophagoides ptrenyssnus)、褐黄血蜱(Haemaphysalis flava)、卵形硬蜱(Ixodes ovatus)、Phyllocoptruta citri、苹刺瘿螨(Aculus schlechtendali)、苹果全爪螨(Panonychus ulmi)、美洲花蜱(Amblyomma americanum)及鸡皮刺螨(Dermanyssusgallinae)、罗宾根螨(Rhyzoglyphus robini)、生卡螨的一种(Sancassania sp.)等。
作为等翅目害虫,例如可列举出Reticulitermes miyatakei、小楹白蚁(Incisitermes minor)、家白蚁(Coptotermes formosanus)、日本湿木蚁(Hodotermopsisjaponica)、散白蚁(Reticulitermes sp.)、黄胸散白蚁(Reticulitermes flavicepsamamianus)、Glyptotermes kushimensis、广州乳白蚁(Coptotermes guangzhoensis)、恒春新白蚁(Neotermes koshunensis)、Glyptotermes kodamai、赤树白蚁(Glyptotermessatsumensis)、截头堆砂白蚁(Cryptotermes domesticus)、黑翅土白蚁(Odontotermesformosanus)、Glyptotermes nakajimai、近扭白蚁(Pericapritermes nitobei)及栖北散白蚁(Reticulitermes speratus)等。
作为蜚蠊目害虫,例如可列举出黑胸大蠊(Periplaneta fuliginosa)、德国小蠊(Blattella germanica)、东方蠊(Blatta orientalis)、密西西比黑蠊(Periplanetabrunnea)、拟德国小蠊(Blattella lituricollis)、日本大蠊(Periplaneta japonica)及美洲大蠊(Periplaneta americana)等。
作为蚤目,例如可列举出人蚤(Pulex irritans)、猫蚤(Ctenocephalides felis)及鸡蚤(Ceratophyllus gallinae)等。
作为线虫类,例如可列举出草莓芽线虫(Nothotylenchus acris)、水稻干尖线虫(Aphelenchoides besseyi)、穿刺短体线虫(Pratylenchus penetrans)、北方根结线虫(Meloidogyne hapla)、南方根瘤线虫(Meloidogyne incognita)、罗斯托克异皮线虫(Globodera rostochiensis)、爪哇根结线虫(Meloidogyne javanica)、大豆胞囊线虫(Heterodera glycines)、咖啡短体线虫(Pratylenchus coffeae)、落选短体线虫(Pratylenchus neglectus)及柑桔半穿剌线虫(Tylenchus semipenetrans)等。
作为软体动物类,例如可列举出福寿螺(Pomacea canaliculata)、非洲大蜗牛(Achatina fulica)、双线蛞蝓(Meghimatium bilineatum)、查科蛞蝓(Lehmanninavalentiana)、黄蛞蝓(Limax flavus)及螺蛳(Acusta despecta sieboldiana)等。
此外,本发明的农业园艺用杀虫剂对作为其他害虫的番茄潜叶蛾(Tutaabsoluta)也具有强力的杀虫效果。
此外,作为防除对象之一的动物寄生性的蜱螨,例如可列举出如微小牛蜱(Boophilus microplus)、血红扇头蜱(Rhipicephalus sanguineus)、长角血蜱(Haemaphysalis longicornis)、褐黄血蜱(Haemaphysalis flava)、铃头血蜱(Haemaphysalis campanulata)、嗜群血蜱(Haemaphysalis concinna)、日本血蜱(Haemaphysalis japonica)、北岗血蜱(Haemaphysalis kitaokai)、Haemaphysalis ias、卵形硬蜱(Ixodes ovatus)、日本硬蜱(Ixodes nipponensis)、全沟硬蜱(Ixodespersulcatus)、龟形花蜱(Amblyomma testudinarium)、巨棘血蜱(Haemaphysalismegaspinosa)、网纹革蜱(Dermacentor reticulatus)及台湾革蜱(Dermacentortaiwanesis)这样的真蜱类,如鸡皮刺螨(Dermanyssus gallinae)、森林姬刺螨(Ornithonyssus sylviarum)及囊形刺脂螨(Ornithonyssus bursa)这样的森林姬刺螨类,如危鸡犹沙螨(Eutrombicula wichmanni)、红纤沙螨(Leptotrombidium akamushi)、苍白纤恙螨(Leptotrombidium pallidum)、富士纤恙螨(Leptotrombidium fuji)、土佐纤恙螨(Leptotrombidium tosa)、秋恙螨(Neotrombicula autumnalis)、阿[耳弗雷杜热斯]氏真恙螨(Eutrombicula alfreddugesi)及宫川合轮螨(Helenicula miyagawai)这样的恙虫类,如牙氏姬螯螨(Cheyletiella yasguri)、寄食姬螯螨(Cheyletiella parasitivorax)及布氏姬螯螨(Cheyletiella blakei)这样的肉食螨类,如兔痒螨(Psoroptes cuniculi)、牛皮痒螨(Chorioptes bovis)、耳痒螨(Otodectes cynotis)、人疥螨(Sarcoptesscabiei)及猫恙虫(Notoedres cati)这样的疥螨类,以及如犬蠕形螨(Demodex canis)这样的蠕形螨类等。
作为其他防除对象的跳蚤,例如可列举出属于蚤目(Siphonaptera)的外部寄生性无翅昆虫,更具体而言,可列举出属于人蚤科(Pulicidae)及鼠蚤科(Ceratephyllus)等的跳蚤类。作为属于人蚤科的跳蚤类,例如可列举出犬栉头蚤(Ctenocephalides canis)、猫栉头蚤(Ctenocephalides felis)、人蚤(Pulex irritans)、禽角头蚤(Echidnophagagallinacea)、印鼠客蚤(Xenopsylla cheopis)、缓慢细蚤(Leptopsylla segnis)、具带病蚤(Nosopsyllus fasciatus)及不等单蚤(Monopsyllus anisus)等。
进一步,作为其他防除对象的外部寄生生物,例如可列举出如牛血虱(Haematopinus eurysternus)、驴血虱(Haematopinus asini)、羊虱(Dalmalinia ovis)、牛颚虱(Linognathus vituli)、猪血虱(Haematopinus suis)、阴虱(Phthirus pubis)及头虱(Pediculus capitis)这样的虱类,以及如犬啮毛虱(Trichodectes canis)这样的咬虱类,如三角虻(Tabanus trigonus)、尖喙库蠓(Culicoides schultzei)及装饰短蚋(Simulium ornatum)这样的吸血性双翅目害虫等。此外,作为内部寄生生物,例如可列举出如肺虫、鞭虫、结节虫、胃内寄生虫、蛔虫及丝状虫类这样的线虫类,如曼氏裂头绦虫、阔节裂头绦虫、犬复孔绦虫、多头绦虫、细粒棘球蚴及多房棘球绦虫这样的绦虫类,如日本血吸虫及肝蛭这样的吸虫类,以及如球虫、疟原虫、肠内肉孢子虫、弓形虫及隐孢子虫这样的原生动物等。
以本发明的通式(1)所表示吲哚啉化合物或其盐类作为有效成分的农业园艺用杀虫剂,对给水田作物、旱田作物、果树、蔬菜、其他作物及花卉等造成灾害的所述害虫具有显著的防除效果,因此通过配合预测产生害虫的时期,在害虫产生前或确认到害虫产生时对育苗设施、水田、旱田、果树、蔬菜、其他作物、花卉等的种子、水田水、茎叶或土壤等栽培载体等进行处理,从而发挥本发明的农业园艺用杀虫剂的所期望的效果。其中,优选的使用方式为:对作物、花卉等的育苗土壤、移植时的栽植坑土壤、植株根部、灌溉水、水耕栽培中的栽培水等进行处理,基于经由或不经由土壤而由根吸收本发明化合物的、利用了所谓的渗透转移性的使用方式。
可使用本发明的农业园艺用杀虫剂的有用植物没有特别限定,例如可列举出谷类(例如,水稻、大麦、小麦、黑麦、燕麦、玉米等)、豆类(大豆、小豆、蚕豆、豌豆、芸豆、落花生等)、果树〃果实类(苹果、柑橘类、梨、葡萄、桃、梅、樱桃、核桃、栗子、杏仁、香蕉等)、叶〃蔬果类(卷心菜、番茄、菠菜、西兰花、生菜、洋葱、葱(胡葱、冬葱)、青椒、茄子、草莓、胡椒、秋葵、韭菜等)、根菜类(胡萝卜、马铃薯、白薯、芋头、萝卜、芜菁、藕、牛蒡、大蒜、辣韭等)、加工用作物(棉、麻、糖萝卜、啤酒花、甘蔗、甜菜、橄榄、橡胶、咖啡、烟草、茶等)、瓜类(南瓜、黄瓜、西瓜、香瓜、甜瓜等)、牧草类(鸭茅、高粱、梯牧草、三叶草、紫花苜蓿等)、草类(韩国草、翦股颖等)、香料等鉴赏用作物(薰衣草、迷迭香、百里香、欧芹、胡椒、生姜等)、花卉类(菊、蔷薇、康乃馨、兰、郁金香、百合等)、庭木(银杏、樱类、珊瑚木等)、林木(冷杉类、云杉类、松类、柏、杉、桧、桉等)等植物。
上述“植物”还包含通过古典育种法或基因重组技术而赋予对异噁唑草酮等HPPD抑制剂,咪唑乙烟酸、噻吩磺隆等ALS抑制剂,草甘膦等EPSP合成酶抑制剂,草铵膦等谷氨酰胺合成酶抑制剂,稀禾定等乙酰辅酶A羧化酶抑制剂,溴苯腈、麦草畏、2,4-D等除草剂的耐性而成的植物。
作为通过古典育种法赋予耐性而成的“植物”的例子,有对咪唑乙烟酸等咪唑啉酮类ALS抑制型除草剂具有耐性的菜子、小麦、向日葵、水稻,其已经以Clearfield(注册商标)的商品名称进行贩售。同样地,还有基于古典育种法而对噻吩磺隆等磺酰脲类ALS抑制型除草剂具有耐性的大豆,其已经以STS大豆的商品名称进行贩售。同样地,作为通过古典育种法赋予对三酮肟(Trione oxime)类、芳氧基苯氧基丙酸类除草剂等乙酰辅酶A羧化酶抑制剂的耐性而成的植物的例子,有SR玉米等。
此外,在Proceedings of the National Academy of Sciences of the UnitedStates of America(Proc.Natl.Acad.Sci.USA)87卷、7175~7179页(1990年)等中,记载了赋予对乙酰辅酶A羧化酶抑制剂的耐性而成的植物。此外,在杂草科学(Weed Science)53卷、728~746页(2005年)等中,报告了对乙酰辅酶A羧化酶抑制剂具有耐性的突变乙酰辅酶A羧化酶,通过使用基因重组技术将该突变乙酰辅酶A羧化酶基因导入植物、或者通过将涉及赋予抵抗性的突变导入植物乙酰辅酶A羧化酶中,能够制作出对乙酰辅酶A羧化酶抑制剂具有耐性的植物,进一步,通过将以嵌合修复技术(chimeraplasty technology)(GuraT.1999.Repairing the Genome’s Spelling Mistakes.Science 285:316-318.)为代表的碱基取代突变导入核酸导入至植物细胞内,在植物的乙酰辅酶A羧化酶基因或ALS基因等中导入位点特异性氨基酸取代突变,能够制作出对乙酰辅酶A羧化酶抑制剂或ALS抑制剂等具有耐性的植物,也可对这些植物使用本发明的农业园艺用杀虫剂。
进一步,作为在基因重组植物中出现的毒素,可列举出来自蜡样芽孢杆菌(Bacillus cereus)或蛴螬乳状菌(Bacillus popilliae)的杀虫性蛋白质;来自苏云金芽孢杆菌(Bacillus thuringiensis)的Cry1Ab、Cry1Ac、Cry1F、Cry1Fa2、Cry2Ab、Cry3A、Cry3Bb1或Cry9C等δ-内毒素,VIP1、VIP2、VIP3或VIP3A等杀虫蛋白质;来自线虫的杀虫蛋白质;蝎毒素、蜘蛛毒素、蜂毒素或昆虫特异性神经毒素等由动物产生的毒素;丝状菌类毒素;植物凝集素;凝集素;胰蛋白酶抑制剂、丝氨酸蛋白酶抑制剂、马铃薯块茎特异蛋白、半胱氨酸蛋白酶抑制剂、木瓜蛋白酶抑制剂等蛋白酶抑制剂;蓖麻毒蛋白、玉米-RIP、相思豆毒蛋白、软瓜蛋白(luffin)、肥皂草毒蛋白、异株泻根毒蛋白等核糖体失活蛋白质(RIP);3-羟基类固醇氧化酶、蜕皮甾体尿苷二磷酸葡糖转移酶、胆固醇氧化酶等类固醇代谢酶;蜕皮激素抑制剂;HMG-CoA还原酶;钠通道、钙通道抑制剂等离子通道抑制剂;保幼激素酯酶;利尿激素受体;芪合酶;二苄合酶(bibenzyl synthase);几丁质酶;葡聚糖酶等。
此外,作为在这样的基因重组植物中出现的毒素,还包含Cry1Ab、Cry1Ac、Cry1F、Cry1Fa2、Cry2Ab、Cry3A、Cry3Bb1、Cry9C、Cry34Ab或Cry35Ab等δ-内毒素蛋白质,VIP1、VIP2、VIP3或VIP3A等杀虫蛋白质的混合毒素,缺失了一部分的毒素,经修饰的毒素。混合毒素为使用重组技术,通过这些蛋白质的不同结构域的新组合而制成的。作为缺失了一部分的毒素,已知有缺失了氨基酸序列的一部分的Cry1Ab。作为经修饰的毒素,其中,天然型毒素的氨基酸中的一个或多个被取代。
这些毒素的例子及可合成这些毒素的重组植物记载于EP-A-0 374 753、WO 93/07278、WO 95/34656、EP-A-0 427 529、EP-A-451 878、WO 03/052073等中。
这些重组植物所含的毒素,特别是对植物赋予对甲虫目害虫、半翅目害虫、双翅目害虫、鳞翅目害虫、线虫类的耐性。本发明的农业园艺用杀虫剂可与上述技术同时使用,或者也可进行体系化使用。
为了防除各种害虫,本发明的农业园艺用杀虫剂可直接使用,或用水等进行适当稀释而使用,或以悬浊的形式、以对防除害虫或线虫有效的量而使用于预测产生该害虫及线虫的植物,例如,对于在果树、谷类、蔬菜等中产生的害虫及线虫,除了在茎叶部进行散布以外,还可以进行将种子浸渍于药剂、种子包衣、过氧化钙处理等种子处理,进行土壤全层混合、垄沟施用、苗床土混合、穴盘苗处理、栽植坑处理、株根处理、追肥、水稻的箱处理、水面施用等,处理于土壤等中而使其由根吸收而使用。此外,还可以通过营养液(水耕)栽培中的对营养液的施用、熏烟或树干注入等而使用。
进一步,本发明的农业园艺用杀虫剂可直接使用,或用水等进行适当稀释而使用,或以悬浊的形式、以对防除害虫有效的量而使用于预测产生该害虫的场所即可,例如,除了散布于贮粮害虫、家屋害虫、卫生害虫、森林害虫等以外,还可用作对家屋建材的涂布、熏烟、诱饵等。
作为种子处理的方法,例如可列举出稀释或不稀释液状或固体状的制剂,以液体状态浸渍种子而使药剂浸透于种子的方法;将固体制剂或液状制剂与种子混合,进行包衣处理而使其附着在种子表面的方法;与树脂、聚合物等附着性载体混合而将药剂涂布于种子的方法;在插秧的同时将制剂散布在种子附近的方法等。
进行该种子处理的“种子”是指用于植物繁殖的栽培初期的植物体,除了种子以外,例如可列举出球根、块茎、种薯、株芽、珠芽、鳞茎或插枝栽培用的营养繁殖用的植物体。
实施本发明的使用方法时的植物的“土壤”或“栽培载体”是指用于栽培作物的支持体,特别是表示用于生根的支持体,其材质没有特别限制,只要是植物可生长的材质即可,可以是所谓的土壤、育苗垫、水等,作为具体的素材,例如可以是砂、轻石、蛭石、硅藻土、琼脂、凝胶状物质、高分子物质、石棉、玻璃棉、木材屑、树皮等。
作为对作物茎叶部或贮粮害虫、家屋害虫、卫生害虫或森林害虫等的散布方法,可列举出用水适当稀释乳剂、流动剂等液体制剂或者用水适当稀释可湿性粉剂或可湿性颗粒剂等固体制剂并进行散布的方法;散布粉剂的方法;或熏烟等。
作为对土壤的施用方法,例如可列举出将液体制剂稀释于水中或不进行稀释而施用于植物体的株根或育苗用苗床等的方法,将颗粒剂散布于植物体的株根或用于育苗的苗床等的方法,在播种前或移植前散布粉剂、可湿性粉剂、可湿性颗粒剂、颗粒剂等,使其与土壤整体混合的方法,在播种前或种植植物体前将粉剂、可湿性粉剂、可湿性颗粒剂、颗粒剂等散布于栽植坑、垄沟等的方法等。
作为对水稻育苗箱的施用方法,剂型有时例如因播种时施用、绿化期施用、移植时施用等施用时期而异,但只要以粉剂、可湿性颗粒剂、颗粒剂等剂型进行施用即可。也可通过与培土的混合进行施用,可以进行培土与粉剂、可湿性颗粒剂或颗粒剂等的混合,例如苗床土混合、覆土混合、与培土整体的混合等。也可以仅使培土与各种制剂交互地形成层状而进行施用。
作为对水田的施用方法,通常将大粒剂、袋剂(パック剂)、颗粒剂、可湿性颗粒剂等固体制剂,流动剂、乳剂等液体状制剂散布于处于灌满水状态的水田中。此外,在插秧时,可以将适当的制剂直接散布并注入于土壤中,或是与肥料混合后散布并注入于土壤中。此外,也可通过在出水口或灌溉装置等水田水的流入源中利用乳剂、流动剂等药液,随水的供给而省力地进行施用。
在旱田作物中,在从播种至育苗期中,可以对靠近种子或植物体的栽培载体等进行处理。对于直接播种在旱田的植物,除了对种子进行直接处理以外,优选对栽培中的植物的株根进行处理。也可使用颗粒剂进行散布处理,或将稀释或未稀释于水中的药剂以液状进行灌注处理等。将颗粒剂与播种前的栽培载体混合后进行播种的处理也是一种优选的处理。
作为进行移植的栽培植物的播种、育苗期的处理,除了对种子进行直接处理以外,优选对育苗用苗床的、液状药剂的灌注处理或颗粒剂的散布处理。此外,在定植时以颗粒剂处理栽植坑或者与移植场所周边的栽培载体混合也是一种优选的处理。
本发明的农业园艺用杀虫剂通常按照农药制剂上的常规方法制剂为便于使用的形状而进行使用。
即,本发明的通式(1)所表示的吲哚啉化合物或其盐类以以下方式进行使用即可:将其或根据需要以适当的比例将其与辅助剂同时掺合并溶解、分离、悬浊、混合、含浸、吸附或附着于适当的惰性载体,从而制剂为例如悬浊剂、乳剂、液剂、可湿性粉剂、可湿性颗粒剂、颗粒剂、粉剂、片剂、袋剂等适宜的剂型。
除了有效成分以外,本发明的组合物(农业园艺用杀虫剂或动物寄生生物防除剂)可根据需要含有通常用于农药制剂或动物寄生生物防除剂中的添加成分。作为该添加成分,可列举出固体载体、液体载体等载体,表面活性剂、分散剂、湿润剂、结合剂、粘着赋予剂、增粘剂、着色剂、扩展剂、分散剂、防冻剂、抗凝剂、崩解剂、防分解剂等。此外,根据需要,也可将防腐剂、植物片等用于添加成分。这些添加成分可单独使用,或者也可组合使用两种以上。
作为固体载体,例如可列举出石英、粘土、高岭土、叶蜡石、绢云母、滑石粉、膨润土、酸性白土、绿坡缕石、沸石、硅藻土等天然矿物类,碳酸钙、硫酸铵、硫酸钠、氯化钾等无机盐类,合成硅酸、合成硅酸盐、淀粉、纤维素、植物粉末(例如锯末、椰壳、玉米穗杆、烟叶茎等)等有机固体载体,聚乙烯、聚丙烯、聚偏二氯乙烯等塑料载体,尿素、无机中空体、塑料中空体、气相二氧化硅(fumed silica,白碳)等。这些固体载体可单独使用,或者也可组合使用两种以上。
作为液体载体,例如可列举出如甲醇、乙醇、丙醇、异丙醇、丁醇等一元醇类,或乙二醇、二乙二醇、丙二醇、己二醇、聚乙二醇、聚丙二醇、丙三醇等多元醇类这样的醇类,丙二醇醚等多元醇化合物类,丙酮、甲基乙基酮、甲基异丁酮、二异丁酮、环己酮等酮类,乙醚、二噁烷、乙二醇单乙醚、二丙醚、THF等醚类,正链烷烃、环烷、异链烷烃、煤油、矿油等脂肪族烃类,苯、甲苯、二甲苯、溶剂石脑油、烷基萘等芳香族烃类,二氯甲烷、氯仿、四氯化碳等卤化烃类,乙酸乙酯、邻苯二甲酸二异丙酯、邻苯二甲酸二丁酯、邻苯二甲酸二辛酯、己二酸二甲基酯等酯类,γ-丁内酯等内酯类,二甲基甲酰胺、二乙基甲酰胺、二甲基乙酰胺、N-烷基吡咯烷酮等酰胺类,乙腈等腈类,二甲基亚砜等硫化物类,大豆油、菜子油、绵籽油、蓖麻油等植物油,水等。这些液体载体可单独使用,或者也可组合使用两种以上。
作为用作分散剂或湿展剂的表面活性剂,例如可列举出山梨糖醇酐脂肪酸酯、聚氧乙烯山梨糖醇酐脂肪酸酯、蔗糖脂肪酸酯、聚氧乙烯脂肪酸酯、聚氧乙烯树脂酸酯、聚氧乙烯脂肪酸二酯、聚氧乙烯烷基醚、聚氧乙烯烷基芳基醚、聚氧乙烯烷基苯基醚、聚氧乙烯二烷基苯基醚、聚氧乙烯烷基苯基醚福尔马林缩合物、聚氧乙烯聚氧丙烯嵌段共聚物、聚苯乙烯聚氧乙烯嵌段聚合物、烷基聚氧乙烯聚丙烯嵌段共聚物醚、聚氧乙烯烷基胺、聚氧乙烯脂肪酸酰胺、聚氧乙烯脂肪酸二苯基醚、聚亚烷基苄基苯基醚、聚氧化烯苯乙烯基苯基醚、乙炔二醇、聚氧化烯加成乙炔二醇、聚氧乙烯醚型硅酮、酯型硅酮、氟类表面活性剂、聚氧乙烯蓖麻油、聚氧乙烯氢化蓖麻油等非离子表面活性剂,烷基硫酸盐、聚氧乙烯烷基醚硫酸盐、聚氧乙烯烷基苯基醚硫酸盐、聚氧乙烯苯乙烯基苯基醚硫酸盐、烷基苯磺酸盐、烷基芳基磺酸盐、木质素磺酸盐、烷基磺基琥珀酸盐、萘磺酸盐、烷基萘磺酸盐、萘磺酸的福尔马林缩合物的盐、烷基萘磺酸的福尔马林缩合物的盐、脂肪酸盐、聚羧酸盐、聚丙烯酸盐、N-甲基-脂肪酸肌氨酸盐、树脂酸盐、聚氧乙烯烷基醚磷酸盐、聚氧乙烯烷基苯基醚磷酸盐等阴离子表面活性剂,月桂胺盐酸盐、硬脂胺盐酸盐、油胺盐酸盐、硬脂胺乙酸盐、硬脂氨基丙胺乙酸盐、氯化烷基三甲基铵、烷基二甲基苯扎氯铵(alkyldimethyl benzalkoniumchloride)等烷基胺盐等阳离子表面活性剂,氨基酸型或甜菜碱型等两性表面活性剂等。这些表面活性剂可单独使用,或者也可组合使用两种以上。
作为结合剂或粘着赋予剂,例如可列举出羧甲基纤维素或其盐、糊精、水溶性淀粉、黄原胶、瓜尔胶、蔗糖、聚乙烯吡咯烷酮、阿拉伯树胶、聚乙烯醇、聚乙烯乙酸酯、聚丙烯酸钠、平均分子量为6000~20000的聚乙二醇、平均分子量为10万~500万的聚环氧乙烷、磷脂质(例如脑磷脂、卵磷脂等)纤维素粉末、糊精、加工淀粉、聚氨基羧酸螯合化合物、交联聚乙烯吡咯烷酮、马来酸与苯乙烯类的共聚物、(甲基)丙烯酸类共聚物、由多元醇形成的聚合物与二羧酸酐的半酯、聚苯乙烯磺酸的水溶性盐、石蜡、萜、聚酰胺树脂、聚丙烯酸盐、聚氧乙烯、蜡、聚乙烯基烷基醚、烷基酚福尔马林缩合物、合成树脂乳液等。
作为增粘剂,例如可列举出如黄原胶、瓜尔胶、定优胶(diutan gum)、羧甲基纤维素、聚乙烯吡咯烷酮、羧基乙烯基聚合物、丙烯酸类聚合物、淀粉化合物、多糖类这样的水溶性高分子,如高纯度膨润土、气相二氧化硅(fumed silica,白碳)这样的无机微粉等。
作为着色剂,例如可列举出如氧化铁、氧化钛、普鲁士蓝这样的无机颜料,如茜素染料、偶氮染料、金属酞菁染料这样的有机染料等。
作为防冻剂,例如可列举出乙二醇、二乙二醇、丙二醇、丙三醇等多元醇类等。
作为用于抗凝或促进崩解的辅助剂,例如可列举出淀粉、海藻酸、甘露糖、半乳糖等多糖类,聚乙烯吡咯烷酮、气相二氧化硅(fumed silica,白碳)、酯橡胶、石油树脂、三聚磷酸钠、六偏磷酸钠、硬脂酸金属盐、纤维素粉末、糊精、甲基丙烯酸酯的共聚物、聚乙烯吡咯烷酮、聚氨基羧酸螯合化合物、磺化苯乙烯-异丁烯-马来酸酐共聚物、淀粉-聚丙烯腈接枝共聚物等。
作为防分解剂,例如可列举出如沸石、生石灰、氧化镁这样的干燥剂,酚类化合物、胺化合物、硫化物、磷酸化合物等抗氧化剂,水杨酸化合物、二苯甲酮化合物等紫外线吸收剂等。
作为防腐剂,例如可列举出山梨酸钾、1,2-苯并噻唑啉-3-酮等。
进一步,还可以根据需要使用功能性分散剂、增效醚等代谢分解抑制剂等的活性增强剂、丙二醇等防冻剂、BHT等抗氧化剂、紫外线吸收剂等其他的辅助剂。
有效成分化合物的掺合比例可根据需要增减,在100重量份的本发明的农业园艺用杀虫剂中,有效成分化合物从0.01~90重量份的范围适当选择并使用即可,例如在制成粉剂、颗粒剂、乳剂或可湿性粉剂时,0.01~50重量份(相对于农业园艺用杀虫剂整体的重量为0.01~50重量%)较为适宜。
本发明的农业园艺用杀虫剂的使用量因各种因素,例如,目的、对象害虫、作物的生长状况、害虫的产生倾向、气候、环境条件、剂型、施用方法、施用场所、施用时期等而变动,作为有效成分化合物,根据目的从每10公亩0.001g~10kg、优选从每10公亩0.01g~1kg的范围适当选择即可。
为了扩大防除的对象病害虫、防除的适当时期,或者以谋求降低药量为目的,本发明的农业园艺用杀虫剂也可与其他农业园艺用杀虫剂、杀螨剂、杀线虫剂、杀菌剂、生物农药等混合使用,此外,也可根据使用场所,与除草剂、植物生长调节剂、肥料等混合使用。
作为以上述目的而进行使用的其他农业园艺杀虫剂、杀螨剂、杀线虫剂,例如可例示出3,5-二甲基苯基氨基甲酸甲酯(XMC)、苏云金杆菌鲇泽变种(Bacillus thuringiensisaizawai)、苏云金杆菌以色列亚种(Bacillus thuringiensis israelensis)、苏云金杆菌日本亚种(Bacillus thuringiensis japonensis)、苏云金杆菌库斯塔变种(Bacillusthuringiensis kurstaki)、苏云金杆菌粉甲变种(Bacillus thuringiensistenebrionis)、苏云金杆菌(Bacillus thuringiensis)生成的结晶蛋白质毒素、BPMC、Bt毒素类杀虫性化合物、CPCBS(杀螨酯,chlorfenson)、DCIP(二氯二异丙醚,dichlorodiisopropyl ether)、D-D(1,3-二氯丙烯,1,3-Dichloropropene)、DDT、NAC、O-4-二甲基氨基磺酰基苯基O,O-二乙基硫代磷酸酯(O-4-dimethylsulfamoylphenyl O,O-diethylphosphorothioate,DSP)、O-乙基O-4-硝基苯基苯基硫代磷酸酯(O-ethyl O-4-nitrophenyl phenylphosphonothioate,EPN)、三丙基异氰脲酸酯(TPIC)、氟丙菊酯(acrinathrin)、印楝素(azadirachtin)、保棉磷(azinphos-methyl)、灭螨醌(acequinocyl)、啶虫脒(acetamiprid)、乙酰虫腈(acetoprole)、乙酰甲胺磷(acephate)、阿巴美丁(abamectin)、除虫菌素-B(avermectin-B)、磺胺螨酯(amidoflumet)、双甲脒(amitraz)、棉铃威(alanycarb)、涕灭威(aldicarb)、涕灭砜威(aldoxycarb)、艾氏剂(aldrin)、α-硫丹(alpha-endosulfan)、α-氯氰菊酯(alpha-cypermethrin)、阿苯达唑(albendazole)、丙烯菊酯(allethrin)、氯唑磷(isazofos)、isamidofos、isoamidofos、加福松(isoxathion)、异柳磷(isofenphos)、异丙威(isoprocarb:MIPC)、伊维菌素(ivermectin)、新烟碱类杀线虫剂(imicyafos)、吡虫啉(imidacloprid)、炔咪菊酯(imiprothrin)、茚虫威(indoxacarb)、高氰戊菊酯(esfenvalerate)、乙硫苯威(ethiofencarb)、乙硫磷(ethion)、乙虫腈(ethiprole)、乙螨唑(etoxazole)、醚菊酯(ethofenprox)、丙线磷(ethoprophos)、乙嘧硫磷(etrimfos)、埃玛菌素(emamectin)、甲氨基阿维菌素苯甲酸盐(emamectin-benzoate)、硫丹(endosulfan)、烯炔菊酯(empenthrin)、杀线威(oxamyl)、砜吸磷(oxydemeton-methyl)、异亚砜磷(oxydeprofos:ESP)、奥苯达唑(oxibendazole)、奥吩达唑(oxfendazole)、油酸钾(Potassium oleate)、油酸钠(sodiumoleate)、硫线磷(cadusafos)、巴丹(cartap)、西维因(carbaryl)、丁硫克百威(carbosulfan)、克百威(carbofuryl)、γ-氯氟氰菊酯(gamma-cyhalothrin)、灭杀威(xylylcarb)、喹硫磷(quinalphos)、烯虫炔酯(kinoprene)、灭螨猛(chinomethionat)、地虫威(cloethocarb)、噻虫胺(clothianidin)、四螨嗪(clofentezine)、环虫酰肼(chromafenozide)、氯虫苯甲酰胺(chlorantraniliprole)、氯氧磷(chlorethoxyfos)、杀虫脒(chlordimeform)、氯丹(chlordane)、毒死蜱(chlorpyrifos)、甲基毒死蜱(chlorpyrifos-methyl)、溴虫腈(chlorphenapyr)、杀螨酯(chlorfenson)、毒虫畏(chlorfenvinphos)、定虫隆(chlorfluazuron)、乙酯杀螨醇(chlorobenzilate)、氯代苯甲酸(chlorobenzoate)、开乐散(三氯杀螨醇:dicofol)、杀力松(salithion)、杀螟腈(cyanophos:CYAP)、丁醚脲(diafenthiuron)、除线特(diamidafos)、溴氰虫酰胺(cyantraniliprole)、θ-氯氰菊酯(theta-cypermethrin)、除螨灵(dienochlor)、腈吡螨酯(cyenopyrafen)、蔬果磷(dioxabenzofos)、苯虫醚(diofenolan)、σ-氯氰菊酯(sigma-cypermethrin)、除线磷(dichlofenthion:ECP)、乙氰菊酯(cycloprothrin)、敌敌畏(dichlorvos:DDVP)、乙拌磷(disulfoton)、呋虫胺(dinotefuryl)、氯氟氰菊酯(cyhalothrin)、苯醚氰菊酯(cyphenothrin)、氟氯氰菊酯(cyfluthrin)、除虫脲(diflubenzuron)、丁氟螨酯(cyflumetofen)、氟螨嗪(diflovidazin)、三环锡(cyhexatin)、氯氰菊酯(cypermethrin)、甲基毒虫畏(dimethylvinphos)、乐果(dimethoate)、四氟甲醚菊酯(dimefluthrin)、氟硅菊酯(silafluofen)、灭蝇胺(cyromazine)、乙基多杀菌素(spinetoram)、多杀菌素(spinosad)、螺螨酯(spirodiclofen)、螺虫乙酯(spirotetramat)、螺甲螨酯(spiromesifen)、氟虫胺(sulfluramid)、硫丙磷(sulprofos)、氟啶虫胺腈(sulfoxaflor)、δ-氯氰菊酯(zeta-cypermethrin)、二嗪农(diazinon)、氟胺氰菊酯(tau-fluvalinate)、棉隆(dazomet)、噻虫啉(thiacloprid)、噻虫嗪(thiamethoxam)、硫双灭多威(thiodicarb)、杀虫环(thiocyclam)、thiosultap、杀虫双(thiosultap-sodium)、硫磷嗪(thionazin)、甲基乙拌磷(thiometon)、避蚊胺(deet)、狄氏剂(dieldrin)、杀虫畏(tetrachlorvinphos)、三氯杀螨砜(tetradifon)、四氟醚菊酯(tetramethylfluthrin)、胺菊酯(tetramethrin)、丁基嘧啶磷(tebupirimfos)、虫酰肼(tebufenozide)、吡螨胺(tebufenpyrad)、七氟菊酯(tefluthrin)、伏虫隆(teflubenzuron)、异吸硫磷(demeton-S-methyl)、双硫磷(temephos)、溴氰菊酯(deltamethrin)、特丁磷(terbufos)、溴代吡咯腈(tralopyril)、四溴菊酯(tralomethrin)、四氟苯菊酯(transfluthrin)、唑蚜威(triazamate)、唑呀威(triazuron)、水杨菌胺(trichlamide)、敌百虫(trichlorphon:DEP)、杀虫隆(triflumuron)、唑虫酰胺(tolfenpyrad)、二溴磷(naled:BRP)、硝虫噻嗪(nithiazine)、烯啶虫胺(nitenpyram)、双苯氟脲(novaluron)、多氟脲(noviflumuron)、烯虫乙酯(hydroprene)、氟吡唑虫(vaniliprole)、蚜灭多(vamidothion)、对硫磷(parathion)、甲基对硫磷(parathion-methyl)、苄螨醚(halfenprox)、氯虫酰肼(halofenozide)、双三氟虫脲(bistrifluron)、杀虫双(bisultap)、氟蚁腙(hydramethylnon)、羟丙基淀粉(hydroxypropyl starch)、乐杀螨(binapacryl)、联苯肼酯(bifenazate)、氟氯菊酯(bifenthrin)、吡蚜酮(pymetrozine)、吡唑硫磷(pyraclorfos)、嘧啶威(pyrafluprole)、哒嗪硫磷(pyridafenthion)、哒螨酮(pyridaben)、啶虫丙醚(pyridalyl)、吡氟喹虫唑(pyrifluquinazon)、吡唑虫啶(pyriprole)、蚊蝇醚(pyriproxyfen)、抗蚜威(pirimicarb)、嘧螨醚(pyrimidifen)、甲基嘧啶磷(pirimiphos-methyl)、除虫菊酯(pyrethrins)、氟虫腈(fipronil)、喹螨醚(fenazaquin)、苯线磷(fenamiphos)、溴螨酯(bromopropylate)、杀螟硫磷(fenitrothion:MEP)、苯氧威(fenoxycarb)、苯硫威(fenothiocarb)、苯醚菊酯(phenothrin)、仲丁威(fenobucarb)、丰索磷(fensulfothion)、倍硫磷(fenthion:MPP)、稻丰散(phenthoate:PAP)、氰戊菊酯(fenvalerate)、唑螨酯(fenpyroximate)、甲氰菊酯(fenpropathrin)、芬苯达唑(fenbendazole)、噻唑磷(fosthiazate)、伐虫脒(formetanate)、特嘧硫磷(butathiofos)、噻嗪酮(buprofezin)、呋线威(furathiocarb)、炔丙菊酯(prallethrin)、嘧螨酯(fluacrypyrim)、氟啶胺(fluazinam)、氟啶蜱脲(fluazuron)、氟噻虫砜(fluensulfone)、氟螨脲(flucycloxuron)、氟氰戊菊酯(flucythrinate)、氟胺氰菊酯(fluvalinate)、吡氟硫磷(flupyrazofos)、嘧虫胺(flufenerim)、氟虫脲(flufenoxuron)、氟螨嗪(flufenzine)、三氟醚菊酯(flufenprox)、苄螨醚(fluproxyfen)、溴氟菊酯(flubrocythrinate)、氟虫双酰胺(flubendiamide)、氟氯苯菊酯(flumethrin)、flurimfen、丙硫磷(prothiofos)、protrifenbute、氟啶虫酰胺(flonicamid)、丙虫磷(propaphos)、炔螨特(propargite:BPPS)、丙溴磷(profenofos)、丙氟菊酯(profluthrin)、残杀威(propoxur:PHC)、溴螨酯(bromopropylate)、β-氟氯氰菊酯(beta-cyfluthrin)、氟铃脲(hexaflumuron)、噻螨酮(hexythiazox)、庚烯磷(heptenophos)、氯菊酯(permethrin)、异噻虫唑(benclothiaz)、恶虫威(bendiocarb)、杀虫磺(bensultap)、苯螨特(benzoximate)、丙硫克百威(benfuracarb)、辛硫磷(phoxim)、伏杀磷(phosalone)、噻唑磷(fosthiazate)、丁环硫磷(fosthietan)、磷胺(phosphamidon)、磷虫威(phosphocarb)、亚胺硫磷(phosmet:PMP)、多萘菌素(polynactins)、伐虫脒(formetanate)、安果(formothion)、甲拌磷(phorate)、机油(machineoil)、马拉硫磷(malathion)、密比霉素(milbemycin)、密比霉素A(milbemycin-A)、密灭汀(milbemectin)、灭蚜磷(mecarbam)、倍硫磷亚砜(mesulfenfos)、灭多虫(methomyl)、蜗牛敌(metaldehyde)、氰氟虫腙(metaflumizone)、甲胺磷(methamidophos)、安百亩(metam-ammonium)、威百亩(metam-sodium)、灭虫威(methiocarb)、杀扑磷(methidathion:DMTP)、异硫氰酸甲酯(methylisothiocyanate)、甲基新癸酰胺(methylneodecanamide)、甲基对硫磷(methylparathion)、噁虫酮(metoxadiazone)、甲氧滴滴涕(methoxychlor)、甲氧虫酰肼(methoxyfenozide)、甲氧苄氟菊酯(metofluthrin)、烯虫酯(methoprene)、速灭威(metolcarb)、氯氟醚菊酯(meperfluthrin)、速灭磷(mevinphos)、久效磷(monocrotophos)、杀虫单(monosultap)、λ-氯氟氰菊酯(lambda-cyhalothrin)、利阿诺定(ryanodine)、虱螨脲(lufenuron)、苄呋菊酯(resmethrin)、雷皮菌素(lepimectin)、鱼藤酮(rotenone)、盐酸左旋咪唑(levamisol hydrochloride)、苯丁锡(fenbutatin oxide)、酒石酸甲噻吩嘧啶(morantel tartarate)、溴化甲烷(methylbromide)、三环己基氢氧化锡(cyhexatin)、氰氨化钙(calcium cyanamide)、多硫化钙(calciumpolysulfide)、硫磺(sulfur)及硫酸烟碱(nicotine-sulfate)等。
作为以相同目的而使用的农业园艺用杀菌剂,例如可例示出金色制霉素(aureofungin)、阿扎康唑(azaconazole)、氧化福美双杀菌剂(azithiram)、acypetacs、活化酯(acibenzolar)、苯并噻二唑(acibenzolar-S-methyl)、嘧菌酯(azoxystrobin)、敌菌灵(anilazine)、吲唑磺菌胺(amisulbrom)、1-氨基丙基磷酸(ampropylfos)、唑嘧菌胺(ametoctradin)、烯丙醇(allyl alcohol)、杀螟丹(aldimorph)、代森铵(amobam)、异噻菌胺(isotianil)、异酰菌酮(isovaledione)、萘吡菌胺(isopyrazam)、稻瘟灵(isoprothiolane)、种菌唑(ipconazole)、异菌脲(iprodione)、异丙菌胺(iprovalicarb)、异稻瘟净(iprobenfos)、抑霉唑(imazalil)、双胍辛胺(iminoctadine)、双胍辛胺-烷苯磺酸盐(iminoctadine-albesilate)、双胍辛胺-三乙酸盐(iminoctadine-triacetate)、酰胺唑(imibenconazole)、烯效唑(uniconazole)、烯效唑-P(uniconazole-P)、氯唑灵(echlomezole)、克瘟散(edifenphos)、乙环唑(etaconazole)、噻唑菌胺(ethaboxam)、乙菌定(ethirimol)、伊特姆(etem)、乙氧喹(ethoxyquin)、土菌灵(etridiazole)、烯肟菌酯(enestroburin)、氟环唑(epoxiconazole)、噁霜灵(oxadixyl)、氧化萎锈灵(oxycarboxin)、8-羟基喹啉铜(copper-8-quinolinolate)、土霉素(oxytetracycline)、喹啉铜(copper-oxinate)、噁咪唑(oxpoconazole)、噁咪唑富马酸盐(oxpoconazole-fumarate)、噁喹酸(oxolinic acid)、辛噻酮(octhilinone)、呋酰胺(ofurace)、肟醚菌胺(orysastrobin)、威百亩(metam-sodium)等土壤杀菌剂、春雷霉素(kasugamycin)、吗菌威(carbamorph)、环丙酰菌胺(carpropamid)、多菌灵(carbendazim)、萎锈灵(carboxin)、香芹酮(carvone)、醌菌腙(quinazamid)、羟基喹啉基乙酮(quinacetol)、喹氧灵(quinoxyfen)、灭螨猛(quinomethionate)、敌菌丹(captafol)、克菌丹(captan)、精苯霜灵(kiralaxyl)、氯苯喹唑(quinconazole)、五氯硝基苯(quintozene)、双胍盐(guazatine)、硫杂灵(cufraneb)、福美铜氯(cuprobam)、果绿定(glyodin)、灰黄霉素(griseofulvin)、甘宝素(climbazole)、甲酚(cresol)、醚菌酯(kresoxim-methyl)、乙菌利(chlozolinate)、克霉唑(clotrimazole)、灭瘟唑(chlobenthiazone)、双胺灵(chloraniformethan)、四氯对醌(chloranil)、四氯喹噁啉(chlorquinox)、氯化苦(chloropicrin)、苯咪唑菌(chlorfenazole)、氯二硝基萘(chlorodinitronaphthalene)、百菌清(chlorothalonil)、地茂散(chloroneb)、氰菌胺(zarilamid)、水杨酰苯胺(salicylanilide)、氰霜唑(cyazofamid)、焦碳酸二乙酯(diethyl pyrocarbonate)、乙霉威(diethofencarb)、环菌胺(cyclafuramid)、双氯氰菌胺(diclocymet)、菌核利(dichlozoline)、苄氯三唑醇(diclobutrazol)、抑菌灵(dichlofluanid)、放线菌酮(cycloheximide)、哒菌清(diclomezine)、氯硝胺(dicloran)、双氯酚(dichlorophen)、二氯萘醌(dichlone)、双硫仑(disulfiram)、灭菌磷(ditalimfos)、二噻农(dithianon)、烯唑醇(diniconazole)、烯唑醇-M(diniconazole-M)、代森锌(zineb)、敌螨普(dinocap)、邻敌螨消(dinocton)、硝辛酯(dinosulfon)、硝丁酯(dinoterbon)、敌螨通(dinobuton)、硝戊酯(dinopenton)、双硫氧吡啶(dipyrithione)、二苯胺(diphenylamine)、苯醚甲环唑(difenoconazole)、环氟菌胺(cyflufenamid)、二氟林(diflumetorim)、环唑醇(cyproconazole)、嘧菌环胺(cyprodinil)、酯菌胺(cyprofuram)、氰菌灵(cypendazole)、硅氟唑(simeconazole)、甲菌定(dimethirimol)、烯酰吗啉(dimethomorph)、霜脲氰(cymoxanil)、醚菌胺(dimoxystrobin)、甲基溴(methyl bromide)、福美锌(ziram)、硅噻菌胺(silthiofam)、链霉素(streptomycin)、螺环菌胺(spiroxamine)、戊苯砜(sultropen)、环苯吡菌胺(sedaxane)、苯酰菌胺(zoxamide)、棉隆(dazomet)、代森环(thiadiazin)、噻酰菌胺(tiadinil)、噻二唑(thiadifluor)、噻菌灵(thiabendazole)、硫氰苯甲酰胺(tioxymid)、硫氯苯亚胺(thiochlorfenphim)、硫菌灵(thiophanate)、甲基硫菌灵(thiophanate-methyl)、噻菌腈(thicyofen)、克杀螨(thioquinox)、灭螨猛(chinomethionat)、噻呋酰胺(thifluzamide)、福美双(thiram)、癸磷锡(decafentin)、四氧硝基苯(tecnazene)、叶枯酞(tecloftalam)、福代硫(tecoram)、氟醚唑(tetraconazole)、咪菌威(debacarb)、脱氢乙酸(dehydroacetic acid)、戊唑醇(tebuconazole)、异丁乙氧喹啉(tebufloquin)、多地辛(dodicin)、多果定(dodine)、十二烷基苯磺酸双乙二胺铜络盐(II)(DBEDC)、吗菌灵(dodemorph)、敌菌酮(drazoxolon)、三唑醇(triadimenol)、三唑酮(triadimefon)、丁三唑(triazbutil)、唑菌嗪(triazoxide)、威菌磷(triamiphos)、嘧菌醇(triarimol)、水杨菌胺(trichlamide)、三环唑(tricyclazole)、灭菌唑(triticonazole)、十三吗啉(tridemorph)、三丁基氧化锡(tributyltin oxide)、氟菌唑(triflumizole)、肟菌酯(trifloxystrobin)、嗪氨灵(triforine)、对甲抑菌灵(tolylfluanid)、甲基立枯磷(tolclofos-methyl)、游霉素(natamycin)、代森钠(nabam)、酞菌酯(nitrothal-isopropyl)、硝基苯乙烯(nitrostyrene)、氟苯嘧啶醇(nuarimol)、壬基酚磺酸铜(coppernonylphenol sulfonate)、丙烯酸喹啉酯(halacrinate)、有效霉素(validamycin)、缬菌胺(valifenalate)、超敏蛋白(harpin protein)、联苯吡菌胺(bixafen)、啶氧菌酯(picoxystrobin)、氟吡菌胺(picobenzamide)、硫双二氯酚(bithionol)、双苯三唑醇(bitertanol)、土菌消(hydroxyisoxazole)、羟基异噁唑钾(hydroisoxazole-potassium)、乐杀螨(binapacryl)、联苯(biphenyl)、粉病灵(piperalin)、恶霉灵(hymexazol)、唑菌酯(pyraoxystrobin)、比锈灵(pyracarbolid)、吡唑醚菌酯(pyraclostrobin)、定菌磷(pyrazophos)、唑胺菌酯(pyrametostrobin)、甲氧苯啶菌(pyriofenone)、啶菌腈(pyridinitril)、啶斑肟(pyrifenox)、吡菌苯威(pyribencarb)、嘧霉胺(pyrimethanil)、甲氧氯吡啶(pyroxychlor)、氯吡呋醚(pyroxyfur)、咯喹酮(pyroquilon)、乙烯菌核利(vinclozolin)、噁唑菌酮(famoxadone)、咪菌腈(fenapanil)、咪唑菌酮(fenamidone)、敌磺钠(fenaminosulf)、氯苯嘧啶醇(fenarimol)、种衣酯(fenitropan)、稻瘟酰胺(fenoxanil)、嘧菌腙(ferimzone)、福美铁(ferbam)、三苯锡(fentin)、拌种咯(fenpiclonil)、胺苯吡菌酮(fenpyrazamine)、腈苯唑(fenbuconazole)、甲呋酰胺(fenfuram)、苯锈啶(fenpropidin)、丁苯吗啉(fenpropimorph)、环酰菌胺(fenhexamid)、苯酞(phthalide)、丁硫啶(buthiobate)、丁胺(butylamine)、磺酸丁嘧啶(bupirimate)、麦穗宁(fuberidazole)、杀稻瘟菌素-S(blasticidin-S)、呋吡菌胺(furametpyr)、呋霜灵(furalaxyl)、嘧螨酯(fluacrypyrim)、氟啶胺(fluazinam)、氟嘧菌酯(fluoxastrobin)、氟苯三唑(fluotrimazole)、氟吡菌胺(fluopicolide)、氟吡菌酰胺(fluopyram)、氟酰亚胺(fluoroimide)、二甲呋酰胺(furcarbanil)、氟唑菌酰胺(fluxapyroxad)、氟喹唑(fluquinconazole)、呋菌唑(furconazole)、呋醚唑(furconazole-cis)、咯菌腈(fludioxonil)、氟硅唑(flusilazole)、磺菌胺(flusulfamide)、噻唑烷类杀菌剂(flutianil)、氟酰胺(flutolanil)、粉唑醇(flutriafol)、糠醛(furfural)、拌种胺(furmecyclox)、氟联苯菌(flumetover)、氟吗啉(flumorph)、丙氧喹啉(proquinazid)、咪鲜胺(prochloraz)、腐霉利(procymidone)、胺丙威(prothiocarb)、丙硫菌唑(prothioconazole)、霜霉威(propamocarb)、丙环唑(propiconazole)、甲基代森锌(propineb)、呋菌隆(furophanate)、噻菌灵(probenazole)、糠菌唑(bromuconazole)、六氯丁二烯(hexachlorobutadiene)、己唑醇(hexaconazole)、环己硫磷(hexylthiofos)、3-苯并[b]噻吩-2-基-5,6-二氢-1,4,2-噁噻嗪4-氧化物(bethoxazin)、苯霜灵(benalaxyl)、苯霜灵M(benalaxyl-M)、麦锈灵(benodanil)、苯菌灵(benomyl)、稻瘟酯(pefurazoate)、敌菌腙(benquinox)、戊菌唑(penconazole)、抑菌啉(benzamorf)、戊菌隆(pencycuron)、苯甲羟肟酸(benzohydroxamic acid)、丙唑草隆(bentaluron)、苯噻硫氰(benthiazole)、苯噻菌胺(benthiavalicarb-isopropyl)、吡噻菌胺(penthiopyrad)、戊苯吡菌胺(penflufen)、啶酰菌胺(boscalid)、氯瘟磷(phosdiphen)、三乙膦酸(fosetyl)、三乙膦酸铝(fosetyl-Al)、多氧霉素(polyoxins)、保粒霉素(polyoxorim)、福代锌(polycarbamate)、灭菌丹(folpet)、甲醛(formaldehyde)、机油(machine oil)、代森锰(maneb)、代森锰锌(mancozeb)、双炔酰菌胺(mandipropamid)、甲菌利(myclozolin)、腈菌唑(myclobutanil)、米多霉素(mildiomycin)、代森环(milneb)、苯并威(mecarbinzid)、磺菌威(methasulfocarb)、间氯敌菌酮(metazoxolon)、威百亩(metam)、威百亩钠(metam-sodium)、甲霜灵(metalaxyl)、精甲霜灵(metalaxyl-M)、代森联(metiram)、异硫氰酸甲酯(methylisothiocyanate)、甲基敌螨普(mepthyldinocap)、叶菌唑(metconazole)、噻菌胺(metsulfovax)、呋菌胺(methfuroxam)、苯氧菌胺(metominostrobin)、苯菌酮(metrafenone)、嘧菌胺(mepanipyrim)、甲霜灵(mefenoxam)、消螨多(meptyldinocap)、担菌宁(mepronil)、灭锈胺(mebenil)、碘代甲烷(iodomethane)、吡咪唑(rabenzazole)、苯扎氯铵(benzalkonium chloride)、碱性氯化铜(basic copper chloride)、碱性硫酸铜(basic copper sulfate)、金属银(silver)等无机杀菌剂、次氯酸钠(sodiumhypochlorote)、氢氧化铜(cupric hydroxide)、可湿性硫粉剂(wettable sulfur)、石硫合剂(calcium polysulfide)、碳酸氢钾(potassium hydrogen carbonate)、碳酸氢钠(sodium hydrogen carbonate)、无机硫磺(sulfur)、无水硫酸铜(copper sulfateanhydride)、二甲基二硫代氨基甲酸镍(nickel dimethyldithiocarbamate)、如8-羟基喹啉铜(oxine copper)这样的铜类化合物、硫酸锌(zinc sulfate)、五水硫酸铜(coppersulfate pentahydrate)等。
同样地,作为除草剂,例如可例示出1-萘乙酰胺、2,4-PA、2,3,6-TBA、2,4,5-T、2,4,5-TB、2,4-D、2,4-DB、2,4-DEB、2,4-DEP、3,4-DA、3,4-DB、3,4-DP、4-CPA、4-CPB、4-CPP、MCP、MCPA、2甲4氯乙硫酯(MCPA-Thioethyl)、MCPB、碘苯腈(ioxynil)、苯草醚(aclonifen)、唑啶草酮(azafenidin)、三氟羧草醚(acifluorfen)、叠氮津(aziprotryne)、四唑嘧磺隆(azimsulfuron)、磺草灵(asulam)、乙草胺(acetochlor)、莠去津(atrazine)、莠去通(atraton)、疏草隆(anisuron)、莎稗磷(anilofos)、四烯雌酮(aviglycine)、脱落酸(abscisic acid)、胺唑草酮(amicarbazone)、酰嘧磺隆(amidosulfuron)、杀草强(amitrole)、环丙嘧啶酸(aminocyclopyrachlor)、氯氨吡啶酸(aminopyralid)、特草嗪酮(amibuzin)、甲基胺草磷(amiprophos-methyl)、ametridione、莠灭净(ametryn)、甲草胺(alachlor)、草毒死(allidochlor)、枯杀达(alloxydim)、五氯戊酮酸(alorac)、异噁隆(isouron)、草特灵(isocarbamid)、异噁氯草酮(isoxachlortole)、异噁草醚(isoxapyrifop)、异噁唑草酮(isoxaflutole)、异噁草胺(isoxaben)、异草定(isocil)、异草完隆(isonoruron)、异丙隆(isoproturon)、异乐灵(isopropalin)、氮萆草(isopolinate)、丁嗪草酮(isomethiozin)、抗倒胺(inabenfide)、抑草津(ipazine)、三唑酰草胺(ipfencarbazone)、丙草定(iprymidam)、灭草喹(imazaquin)、甲基咪草烟(imazapic)、灭草烟(imazapyr)、甲基咪草烟(imazamethapyr)、咪草酯(imazamethabenz)、咪草酸(imazamethabenz-methyl)、甲氧咪草烟(imazamox)、咪草烟(imazethapyr)、唑吡嘧磺隆(imazosulfuron)、三嗪茚草胺(indaziflam)、茚草酮(indanofan)、吲哚啉酪酸(indolebutyric acid)、烯效唑-P(uniconazole-P)、甘草津(eglinazine)、禾草畏(esprocarb)、胺苯磺隆(ethametsulfuron)、甲基胺苯磺隆(ethametsulfuron-methyl)、丁氟消草(ethalfluralin)、抑草威(ethiolate)、吲熟酯(ethychlozate ethyl)、磺噻隆(ethidimuron)、硝草酚(etinofen)、乙烯利(ethephon)、乙氧嘧磺隆(ethoxysulfuron)、氟乳醚(ethoxyfen)、乙胺草醚(etnipromid)、乙呋草磺(ethofumesate)、乙氧苯草胺(etobenzanid)、磺唑草(epronaz)、抑草蓬(erbon)、草藻灭(endothal)、噁草酮(oxadiazon)、丙炔噁草酮(oxadiargyl)、氯噁嗪草(oxaziclomefone)、环丙氧磺隆(oxasulfuron)、草哒松噁杀草敏(oxapyrazon)、乙氧氟草醚(oxyfluorfen)、氨磺乐灵(oryzalin)、嘧苯胺磺隆(orthosulfamuron)、坪草丹(orbencarb)、唑草胺(cafenstrole)、cambendichlor、威磺灵(carbasulam)、唑草酮(carfentrazone)、唑酮草酯(carfentrazone-ethyl)、卡灵草(karbutilate)、长杀草(carbetamide)、异噁甲草威(carboxazole)、喹禾灵(quizalofop)、精喹禾灵(quizalofop-P)、喹禾灵(quizalofop-ethyl)、二甲苯草胺(xylachlor)、灭藻醌(quinoclamine)、氯藻胺(quinonamid)、二氯喹啉酸(quinclorac)、氯甲喹啉酸(quinmerac)、苄草隆(cumyluron)、碘氯啶酯(cliodinate)、草甘膦(glyphosate)、草铵膦(glufosinate)、草铵膦-P(glufosinate-P)、醚草敏(credazine)、烯草酮(clethodim)、坐果酸(cloxyfonac)、游离炔草酸(clodinafop)、炔草酯(clodinafop-propargyl)、绿麦隆(chlorotoluron)、二氯吡啶酸(clopyralid)、cloproxydim、调果酸(cloprop)、氯溴隆(chlorbromuron)、氯丁草(clofop)、异噁草酮(clomazone)、氯硝醚(chlomethoxynil)、甲氧除草醚(chlomethoxyfen)、稗草胺(clomeprop)、炔禾灵(chlorazifop)、可乐津(chlorazine)、氯酯磺草胺酸(cloransulam)、地快尔(chloranocryl)、草灭平(chloramben)、氯酯磺草胺(cloransulam-methyl)、氯草敏(chloridazon)、氯嘧磺隆(chlorimuron)、氯嘧磺隆(chlorimuron-ethyl)、氯磺隆(chlorsulfuron)、氯酞酸(chlorthal)、草克乐(chlorthiamid)、绿麦隆(chlortoluron)、草枯醚(chlornitrofen)、伐草克(chlorfenac)、燕麦酯(chlorfenprop)、氯炔灵(chlorbufam)、氟咪杀(chlorflurazole)、整形醇(chlorflurenol)、chlorprocarb、氯苯胺灵(chlorpropham)、矮壮素(chlormequat)、乙氧苯隆(chloreturon)、羟敌草腈(chloroxynil)、枯草隆(chloroxuron)、三氯丙酸(chloropon)、苯嘧磺草胺(saflufenacil)、草净津(cyanazine)、氰草净(cyanatryn)、燕麦敌(di-allate)、敌草隆(diuron)、diethamquat、麦草畏(dicamba)、环莠隆(cycluron)、草灭特(cycloate)、噻草酮(cycloxydim)、双氯磺草胺(diclosulam)、环丙嘧磺隆(cyclosulfamuron)、2,4-滴丙酸(dichlorprop)、精2,4-滴丙酸(dichlorprop-P)、敌草腈(dichlobenil)、二氯苯氧基丙酸(diclofop)、禾草灵(diclofop-methyl)、苄胺灵(dichlormate)、氯双脲(dichloralurea)、敌草快(diquat)、咯草隆(cisanilide)、2,4-滴硫钠(disul)、环草隆(siduron)、氟硫草定(dithiopyr)、敌乐胺(dinitramine)、吲哚酮草酯(cinidon-ethyl)、戊硝酚(dinosam)、醚磺隆(cinosulfuron)、地乐酚(dinoseb)、特乐酚(dinoterb)、地乐特(dinofenate)、硝丙酚(dinoprop)、氰氟草酯(cyhalofop-butyl)、草乃敌(diphenamid)、枯莠隆(difenoxuron)、戊味禾草灵(difenopenten)、野燕枯(difenzoquat)、洒布净(cybutryne)、环丙津(cyprazine)、三环噻草胺(cyprazole)、吡氟草胺(diflufenican)、氟吡草腙(diflufenzopyr)、杀草净(dipropetryn)、环酰草胺(cypromid)、牧草快(cyperquat)、赤霉素(gibberellin)、西玛津(simazine)、敌灭生(dimexano)、克草胺(dimethachlor)、草哒酮(dimidazon)、异戊乙净(dimethametryn)、二甲吩草胺(dimethenamid)、西草净(simetryn)、西玛通(simeton)、哌草丹(dimepiperate)、噁唑隆(dimefuron)、环庚草醚(cinmethylin)、灭草灵(swep)、sulglycapin、磺草酮(sulcotrione)、草克死(sulfallate)、甲磺草胺(sulfentrazone)、磺酰磺隆(sulfosulfuron)、甲嘧磺隆(sulfometuron)、甲嘧磺隆甲酯(sulfometuron-methyl)、密草通(secbumeton)、稀禾定(sethoxydim)、另丁津(sebuthylazine)、特草定(terbacil)、香草隆(daimuron)、棉隆(dazomet)、茅草枯(dalapon)、噻氟隆(thiazafluron)、噻草啶(thiazopyr)、噻酮磺隆(thiencarbazone)、噻酮磺隆(thiencarbazone-methyl)、仲草丹(tiocarbazil)、硫胺草啶碱(tioclorim)、禾草丹(thiobencarb)、噻二唑草胺(thidiazimin)、噻苯隆(thidiazuron)、噻磺隆(thifensulfuron)、噻吩磺隆(thifensulfuron-methyl)、甜菜安(desmedipham)、敌草净(desmetryn)、四氟隆(tetrafluron)、噻吩草胺(thenylchlor)、牧草胺(tebutam)、丁唑隆(tebuthiuron)、甲氧去草净(terbumeton)、吡喃草酮(tepraloxydim)、特糠酯酮(tefuryltrione)、环磺酮(tembotrione)、异丁草胺(delachlor)、特草定(terbacil)、芽根灵(terbucarb)、特丁草胺(terbuchlor)、特丁津(terbuthylazine)、去草净(terbutryn)、苯吡唑草酮(topramezone)、三甲苯草酮(tralkoxydim)、三嗪氟草胺(triaziflam)、醚苯磺隆(triasulfuron)、野麦畏(tri-allate)、草达津(trietazine)、杀草畏(tricamba)、绿草定(triclopyr)、灭草环(tridiphane)、草达克(tritac)、三氟甲磺隆(tritosulfuron)、氟胺磺隆(triflusulfuron)、氟胺磺隆(triflusulfuron-methyl)、氟乐灵(trifluralin)、三氟啶磺隆(trifloxysulfuron)、茚草酮(tripropindan)、苯磺隆(tribenuron-methyl)、苯磺隆(tribenuron)、三氟苯氧丙酸(trifop)、三氟禾草肟(trifopsime)、三甲隆(trimeturon)、抑草生(naptalam)、萘丙胺(naproanilide)、敌草胺(napropamide)、烟嘧磺隆(nicosulfuron)、甲磺乐灵(nitralin)、除草醚(nitrofen)、三氟甲草醚(nitrofluorfen)、吡氯草胺(nipyraclofen)、草不隆(neburon)、达草灭(norflurazon)、草完隆(noruron)、燕麦灵(barban)、多效唑(paclobutrazol)、百草枯(paraquat)、对氟隆(parafluron)、卤草定(haloxydine)、氟吡禾灵(haloxyfop)、高效氟吡禾灵(haloxyfop-P)、氟吡甲禾灵(haloxyfop-methyl)、氟硝磺酰胺(halosafen)、氯吡嘧磺隆(halosulfuron)、氯吡嘧磺隆(halosulfuron-methyl)、氨氯吡啶酸(picloram)、氟吡草胺(picolinafen)、双环吡喃酮(bicyclopyrone)、双草醚(bispyribac)、双草醚钠(bispyribac-sodium)、比达农(pydanon)、唑啉草酯(pinoxaden)、甲羧除草醚(bifenox)、哌草磷(piperophos)、噁霉灵(hymexazol)、双唑草腈(pyraclonil)、磺酰草吡唑(pyrasulfotole)、苄草唑(pyrazoxyfen)、吡嘧磺隆(pyrazosulfuron)、吡嘧磺隆(pyrazosulfuron-ethyl)、吡唑特(pyrazolate)、双丙氨酰膦(bilanafos)、吡草醚(pyraflufen-ethyl)、氯草定(pyriclor)、pyridafol、pyrithiobac、嘧硫草醚(pyrithiobac-sodium)、达草特(pyridate)、环酯草醚(pyriftalid)、稗草丹(pyributicarb)、嘧啶肟草醚(pyribenzoxim)、吡丙醚(pyrimisulfan)、氟嘧磺隆(primisulfuron)、嘧草醚(pyriminobac-methyl)、砜吡草唑(pyroxasulfone)、甲氧磺草胺(pyroxsulam)、酰苯磺威(fenasulam)、棉胺宁(phenisopham)、非草隆(fenuron)、异噁苯砜(fenoxasulfone)、噁唑禾草灵(fenoxaprop)、精噁唑禾草灵(fenoxaprop-P)、噁唑禾草灵(fenoxaprop-ethyl)、酚硫杀(phenothiol)、2,4,5-涕丙酸(fenoprop)、稀草隆(phenobenzuron)、噻唑禾草灵(fenthiaprop)、氯苯氧乙醇(fenteracol)、四唑酰草胺(fentrazamide)、甜菜宁(phenmedipham)、乙基甜菜宁(phenmedipham-ethyl)、丁草胺(butachlor)、氟丙嘧草酯(butafenacil)、抑草膦(butamifos)、丁噻隆(buthiuron)、特咪唑草(buthidazole)、苏达灭(butylate)、炔草隆(buturon)、丁烯草胺(butenachlor)、丁苯草酮(butroxydim)、地乐胺(butralin)、啶嘧磺隆(flazasulfuron)、麦草氟酯(flamprop)、氟呋草醚(furyloxyfen)、广草胺(prynachlor)、氟嘧磺隆(primisulfuron-methyl)、吡氟禾草灵(fluazifop)、精吡氟禾草灵(fluazifop-P)、吡氟禾草灵(fluazifop-butyl)、异丙吡草酯(fluazolate)、氟草烟(fluroxypyr)、氟硫隆(fluothiuron)、伏草隆(fluometuron)、乙羧氟草醚(fluoroglycofen)、氟咯草酮(flurochloridone)、三氟硝草醚(fluorodifen)、氟化除草醚(fluoronitrofen)、唑啶草(fluoromidine)、氟酮磺隆(flucarbazone)、氟酮磺隆钠(flucarbazone-sodium)、氟消草(fluchloralin)、氟吡磺隆(flucetosulfuron)、嗪草酸(fluthiacet)、嗪草酸甲酯(fluthiacet-methyl)、氟啶嘧磺隆(flupyrsulfuron)、氟噻草胺(flufenacet)、氟苯吡草(flufenican)、氟哒嗪草酯(flufenpyr)、flupropacil、四氟丙酸(flupropanate)、氟胺草唑(flupoxam)、丙炔氟草胺(flumioxazin)、氟烯草酸(flumiclorac)、氟亚胺草酯(flumiclorac-pentyl)、炔草胺(flumipropyn)、三氟噁嗪(flumezin)、伏草隆(fluometuron)、唑嘧磺草胺(flumetsulam)、氟草酮(fluridone)、呋草酮(flurtamone)、氟草烟(fluroxypyr)、丙草胺(pretilachlor)、扑灭生(proxan)、甘扑津(proglinazine)、环丙腈津(procyazine)、氨氟乐灵(prodiamine)、草硫亚胺(prosulfalin)、氟磺隆(prosulfuron)、苄草丹(prosulfocarb)、喔草酯(propaquizafop)、毒草安(propachlor)、扑灭津(propazine)、敌稗(propanil)、炔苯酰草胺(propyzamide)、异丙草胺(propisochlor)、茉莉酮(prohydrojasmon)、嗪咪唑嘧磺隆(propyrisulfuron)、苯胺灵(propham)、氟唑草胺(profluazol)、环丙氟灵(profluralin)、调环酸钙(prohexadione-calcium)、丙苯磺隆(propoxycarbazone)、丙苯磺隆(propoxycarbazone-sodium)、环苯草酮(profoxydim)、除草定(bromacil)、溴杀草敏(brompyrazon)、扑草净(prometryn)、扑灭通(prometon)、溴苯腈(bromoxynil)、杀草全(bromofenoxim)、溴丁酰草胺(bromobutide)、溴草腈(bromobonil)、双氟磺草胺(florasulam)、六氯丙酮(hexachloroacetone)、六嗪酮(hexazinone)、烯草胺(pethoxamid)、草除灵(benazolin)、五氟磺草胺(penoxsulam)、克草猛(pebulate)、氟丁酰草胺(beflubutamid)、灭草猛(vernolate)、黄草伏(perfluidone)、bencarbazone、胺酸杀(benzadox)、苄草胺(benzipram)、苄氨基嘌呤(benzylaminopurine)、噻草隆(benzthiazuron)、双苯嘧草酮(benzfendizone)、地散磷(bensulide)、苄嘧磺隆(bensulfuron-methyl)、新燕灵(benzoylprop)、苯并双环酮(benzobicyclon)、吡草酮(benzofenap)、氟草黄(benzofluor)、灭草松(bentazone)、蔬草灭(pentanochlor)、杀草丹(benthiocarb)、二甲戊乐灵(pendimethalin)、环戊噁草酮(pentoxazone)、氟草胺(benfluralin)、呋草黄(benfuresate)、杀木膦(fosamine)、氟磺胺草醚(fomesafen)、甲酰氨磺隆(foramsulfuron)、吡效隆(forchlorfenuron)、抑芽丹(maleic hydrazide)、2甲4氯丙酸(mecoprop)、精2甲4氯丙酸(mecoprop-P)、地乐施(medinoterb)、二磺隆(mesosulfuron)、甲基二磺隆(mesosulfuron-methyl)、硝草酮(mesotrione)、灭莠津(mesoprazine)、格草净(methoprotryne)、吡草胺(metazachlor)、灭草定(methazole)、双醚氯吡嘧磺隆(metazosulfuron)、噻唑隆(methabenzthiazuron)、苯嗪草酮(metamitron)、噁唑酰草胺(metamifop)、威百亩(metam)、氟烯硝草(methalpropalin)、灭草恒(methiuron)、methiozolin、甲疏苯威(methiobencarb)、甲基杀草隆(methyldymron)、甲氧隆(metoxuron)、磺草唑胺(metosulam)、甲磺隆(metsulfuron)、甲磺隆(metsu1furon-methy1)、二甲哒草伏(metflurazon)、秀谷隆(metobromuron)、吡喃隆(metobenzuron)、醚草通(methometon)、异丙甲草胺(metolachlor)、赛克津(metribuzin)、缩节胺(mepiquat-chloride)、苯噻草胺(mefenacet)、氟磺酰草胺(mefluidide)、庚酰草胺(monalide)、特噁唑隆(monisouron)、灭草隆(monuron)、一氯乙酸(monochloroacetic acid)、绿谷隆(monolinuron)、草达灭(molinate)、伐草快(morfamquat)、碘甲磺隆(iodosulfuron)、碘甲磺隆甲基钠(iodosulfuron-methyl-sodium)、碘草腈(iodobonil)、碘甲烷(iodomethane)、乳氟禾草灵(lactofen)、利谷隆(linuron)、玉嘧磺隆(rimsulfuron)、环草定(lenacil)、硫氰苯胺(rhodethanil)、过氧化钙(calcium peroxide)、溴化甲烷(methyl bromide)等。
此外,作为生物农药,例如通过混合并使用下述物质,能够期待相同的效果。即,核型多角体病毒(Nuclear polyhedrosis virus,NPV)、颗粒体病毒(Granulosis virus,GV)、质型多角体病毒(Cytoplasmic polyhedrosis virus,CPV)、昆虫痘病毒(Entomopoxvirus,EPV)等病毒制剂;瘤捕单顶孢菌(Monacrosporium phymatophagum)、小卷蛾斯氏线虫(Steinernema carpocapsae)、昆虫寄生性线虫(Steinernema kushidai)、穿刺芽孢杆菌(Pasteuria penetrans)等用作杀虫或杀线虫剂的微生物农药;木素木霉(Trichodermalignorum)、放射形土壤杆菌(Agrobacterium radiobactor)、非病原性胡萝卜软腐欧文氏菌(Erwinia carotovora)、枯草芽孢杆菌(Bacillus subtilis)等用作杀菌剂的微生物农药;野油菜黄单胞菌(Xanthomonas campestris)等用作除草剂的生物农药等。
进一步,作为生物农药,例如还可与丽蚜小蜂(Encarsia formosa)、科曼尼蚜茧蜂(Aphidius colemani)、食蚜瘿蚊(Aphidoletes aphidimyza)、潜蝇姬小蜂(Diglyphusisaea)、番茄潜蝇离颚茧蜂(Dacnusa sibirica)、智利小植绥螨(Phytoseiuluspersimilis)、胡瓜钝绥螨(Amblyseius cucumeris)、东亚小花蝽(Orius sauteri)等天敌生物,布氏白僵菌(Beauveria brongniartii)等微生物农药,醋酸(Z)-10-十四烯酯、(E,Z)-4,10-十四碳二烯乙酸酯、(Z)-8-十二烯基乙酸酯、醋酸(Z)-11-十四烯酯、(Z)-13-二十碳烯-10-酮、14-甲基-1-十八碳烯等信息素剂同时使用。
进一步,还适用于驱除寄生在人、家畜、宠物等动物的体内或体外的寄生虫。
以含有本发明的吲哚啉化合物或其盐作为有效成分为特征的动物用的外部寄生虫防除剂、以及以用该外部寄生虫防除剂对动物的外部寄生虫进行处理为特征的动物用外部寄生虫的防除方法也在本发明的范畴内。本发明的化合物通常还可在猫或犬等动物的皮肤上的一处或两处进行点涂或浇注涂布而使用。涂布面积通常为5~10cm2。本发明的化合物优选一旦涂布就遍布动物的整个身体,并且可在不发生结晶化、或者不改变外观或触感的状态下进行干燥。使用量根据动物的重量而优选为0.1~10ml,特别是对于猫而言优选约为0.5~1ml,对于狗而言优选约为0.3~3ml。
对于本发明的外部寄生虫防除剂表现出效力的动物外部寄生虫,作为蚤目害虫,可列举出人蚤(Pulex irritans)等蚤属(Pulex)、猫蚤(Ctenocephalides felis)、犬栉头蚤(Ctenocephalides canis)等栉头蚤属(Ctenocephalides)、印鼠客蚤(Xenopsyllacheopis)等客蚤属(Xenopsylla)、穿皮潜蚤(Tunga penetrans)等的潜蚤属(Tunga)、禽冠蚤(Echidnophaga gallinacea)等冠蚤属(Echidnophaga)、具带病蚤(Nosopsyllusfasciatus)等病蚤属(Nosopsyllus)等。
作为虱目害虫,可列举出头虱(Pediculus humanus capitis)等虱属(Pediculus)、阴虱(Pthirus pubis)等Phtirus属、牛血虱(Haematopinus eurysternus)、猪血虱(Haematopinus suis)等血虱属(Haematopinus)、羊虱(Damalinia ovis)、牛毛虱(Damalinia bovis)等畜虱属(Damalinia)、牛颚虱(Linognathus vituli)、羊颚虱(Linognathus ovillus)等长颚虱属(Linognathus)、水牛盲虱(Solenopotes capillatus)等盲虱属(Solenopotes)等。
作为食毛目害虫,可列举出鸡虱(Menopon gallinae)等禽虱属(Menopon)、Trimenopon spp.、Trinoton spp.、犬啮毛虱(Trichodectes canis)等啮毛虱属(Trichodectes)、猫羽虱(Felicola subrostratus)等猫羽虱属(Felicola)、牛鸟虱(Bovicola bovis)等牛羽虱属(Bovicola)、鸡体虱(Menacanthus stramineus)等刺虱属(Menacanthus)、Werneckiella spp.、Lepikentron spp.等。
作为半翅目害虫,可列举出温带臭虫(Cimex lectularius)、热带臭虫(Cimexhemipterus)等臭虫属(Cimix)、Reduvius senilis等猎蝽属(Reduvius)、齿背猎蝽(Ariluscritatus)等齿背猎蝽属(Arilus)、长红猎蝽(Rhodnius prolixus)等长红猎蝽属(Rhodnius)、红带锥蝽(Triatoma rubrofasciata)等锥猎蝽属(Triatoma)、锥蝽属(Panstrongylus spp.)等。
作为蜱螨目害虫,可列举出美洲钝眼蜱(Amblyomma americanum)、斑点钝眼蜱(Amblyomma maculatum)等钝眼蜱属(Amblyomma)、微小牛蜱(Boophilus microplus)、具环牛蜱(Boophilus annulatus)等牛蜱属(Boophilus)、变异革蜱(Dermacentorvariabilis)、台湾革蜱(Dermacentor taiwanicus)、安氏革蜱(Dermacentor andersoni)等革蜱属(Dermacentor)、长角血蜱(Haemaphysalis longicornis)、褐黄血蜱(Haemaphysalis flava)、何氏血蜱(Haemaphysalis campanulata)等血蜱属(Haemaphysalis)、卵形硬蜱(Ixodes ovatus)、森林硬蜱(Ixodes persulcatus)、肩胛硬蜱(Ixodes scapularis)、太平洋硬蜱(Ixodes pacificus)、全环硬蜱(Ixodes holocyclus)等硬蜱属(Ixodes)、血红扇头蜱(Rhipicephalus sanguineus)、具尾扇头蜱(Rhipicephalus appendiculatus)等扇头蜱属(Rhipicephalus)、波斯锐缘蜱(Argaspersicus)等锐缘蜱属(Argas)、赫氏钝缘软蜱(Ornithodoros hermsi)、回归热钝缘蜱(Ornithodoros turicata)等钝缘蜱属(Ornithodoros)、羊痒螨(Psoroptes ovis)、马痒螨(Psoroptes equi)等疥癣虫属(mange mite)、Knemidocoptes mutans等鸟疥螨属(Knemidocoptes)、猫疥癣虫(Notoedres cati)、鼠疥癣虫(Notoedres muris)等疥癣虫之一属(Notoedres)、人疥螨(Sarcoptes scabiei)等疥螨属(Sarcoptes)、耳痒螨(Otodectescynotis)等耳螨属(Otodectes)、兔囊凸牦螨(Listrophorus gibbus)等Listrophorus属、皮螨属(Chorioptes spp.)、Hypodectes spp.、翼衣螨属(Pterolichus spp.)、胞螨属(Cytodites spp.)、鸡雏螨属(Laminosioptes spp.)、鸡皮刺螨(Dermanyssus gallinae)等皮刺螨属(Dermanyssus)、林禽刺螨(Ornithonyssus sylviarum)、柏氏禽刺螨(Ornithonyssus bacoti)等禽刺螨属(Ornithonyssus)、雅氏瓦螨(Varroa jacobsoni)等瓦螨属(Varroa)、牙氏姬螯螨(Cheyletiella yasguri)、布氏姬螯螨(Cheyletiellablakei)等姬螯螨属(Cheyletiella)、禽螯螨类(Ornithocheyletia spp.)、犬脂螨(Demodex canis)、猫脂螨(Demodex cati)等脂螨属(Demodex)、鼠螨属(Myobia spp.)、疮螨属(Psorergates spp.)、红恙螨(Trombicula akamushi)、苍白恙螨(Trombiculapallida)、小板恙螨(Trombicula scutellaris)等恙螨属(Trombicula),优选蚤目害虫、虱目害虫或蜱螨目害虫。
作为本发明的外部寄生虫防除剂的给药对象的动物,可列举出可成为所述动物外部寄生虫的宿主的动物,通常可列举出作为家畜或宠物而被饲养的恒温动物及变温动物。作为恒温动物,例如可列举出作为哺乳动物的牛、水牛、羊、山羊、猪、骆驼、鹿、黇鹿、驯鹿、马、驴、狗、猫、兔、雪貂、小鼠、大鼠、仓鼠、松鼠、猴等,进一步可列举出作为毛皮动物的水貂、绒鼠、浣熊等,可列举出作为鸟类的鸡、鹅、火鸡、鸭、鸽子、鹦鹉、鹌鹑等。作为变温动物,例如可列举出作为爬行类的陆龟、海龟、绿海龟、星点龟、蜥蜴、鬣蜥、变色龙、壁虎、蟒蛇、游蛇、眼镜蛇等,优选为恒温动物,更优选为狗、猫、牛、马、猪、羊、山羊等哺乳动物。
实施例
以下例示出本发明的代表性的实施例,但本发明并不受其限定。
参考例1.1H-吲哚啉2-羧酸甲酯的制备
[化学式10]
在25mL甲醇中溶解吲哚啉-2-羧酸(1.30g,7.97mmol),在冰冷却下滴加氯化亚砜(1.42g,12.0mmol),搅拌30分钟。然后升温至50℃,搅拌3小时。放冷后,进行减压浓缩,使用乙酸乙酯溶解残渣后,加入饱和碳酸氢钠水溶液。使用乙酸乙酯进行提取,使用水及饱和食盐水进行清洗。使用无水硫酸钠对有机层进行干燥,蒸馏去除溶剂后,通过硅胶层析对得到的残渣进行提纯,得到目标产物(1.08g,72%)。
参考例2.N-乙基磺酰基吲哚啉2-羧酸甲酯的制备
[化学式11]
在20mL四氢呋喃中溶解1H-吲哚啉2-羧酸甲酯(1.08g,5.70mmol)、三乙胺(0.692g,6.84mmol)及N,N-二甲基氨基吡啶(0.348g,2.85mmol),在0℃下滴加乙基磺酰氯(0.928g,6.27mmol),然后在室温下搅拌5小时。在反应液中加入氯化铵水溶液后,使用乙酸乙酯进行提取,使用水及饱和食盐水进行清洗。使用无水硫酸钠对有机层进行干燥,蒸馏去除溶剂后,通过硅胶层析对得到的残渣进行提纯,得到N-乙基磺酰基吲哚啉2-羧酸甲酯(0.760g,49%)。
折射率:1.5366(28.1℃)
参考例3.N-乙基磺酰基吲哚啉2-羧酸的制备
[化学式12]
在10mL乙醇中溶解N-乙基磺酰基吲哚啉2-羧酸甲酯(0.720g,2.67mmol),在0℃下加入5mL氢氧化钾(0.195g,3.48mmol)/水。直接搅拌1小时后,向反应液中加入1N盐酸,使用乙酸乙酯进行提取,使用水及饱和食盐水进行清洗。使用无水硫酸钠对有机层进行干燥,蒸馏去除溶剂,得到N-乙基磺酰基吲哚啉2-羧酸(0.670g,98%)。
熔点:120-122℃
实施例1-1.
1-乙基磺酰基-N-(3-甲基氨基-6-五氟乙基哒嗪-4-基)吲哚啉-2-甲酰胺的制备
[化学式13]
在6.5mL甲苯中溶解N-乙基磺酰基吲哚啉2-羧酸(0.335g,1.31mmol),在冰冷却下依次加入氯化亚砜(0.312g,2.62mmol)、0.5mL的N,N-二甲酰胺,进行1小时加热回流。放冷后,进行减压浓缩,得到N-乙基磺酰基吲哚啉2-甲酰氯。
将该甲酰氯(317mg,1.31mmol)及吡啶(0.311g,1.31mmol)溶解于1.3mL四氢呋喃中,在0℃下,滴加通过WO2016/039441中记载的方法制备的4-氨基-3-甲基氨基-6-五氟乙基哒嗪的四氢呋喃(2mL)溶液后,在室温下搅拌16小时。在反应液中加入氯化铵水溶液后,使用乙酸乙酯进行提取,使用水及饱和食盐水进行清洗。使用无水硫酸钠对有机层进行干燥,蒸馏去除溶剂后,得到粗生成物,其为1-乙基磺酰基-N-(3-甲基氨基-6-五氟乙基哒嗪-4-基)吲哚啉-2-甲酰胺。
实施例1-2.
2-(1-乙基磺酰基吲哚啉-2-基)-3-甲基-6-五氟乙基-3H-咪唑并[4,5-c]哒嗪(化合物编号1-39)的制备
[化学式14]
在甲苯10mL及乙酸2mL中,将实施例1-1中得到的1-乙基磺酰基-N-(3-甲基氨基-6-五氟乙基哒嗪-4-基)吲哚啉-2-甲酰胺加热回流搅拌2小时并放冷后,在减压下对反应液进行浓缩,然后使用乙酸乙酯进行稀释,依次使用碳酸氢化钠水溶液、水、饱和食盐水进行清洗。使用无水硫酸钠干燥有机层,蒸馏去除溶剂后,通过硅胶层析对得到的残渣进行提纯,得到2-(1-乙基磺酰基吲哚啉-2-基)-3-甲基-6-五氟乙基-3H-咪唑并[4,5-c]哒嗪(72.5mg,12%)。
熔点:160-162℃
实施例2.
2-(1-乙基磺酰基-5-氯吲哚啉-2-基)-3-甲基-6-五氟乙基-3H-咪唑并[4,5-c]哒嗪(化合物编号1-41)的制备
[化学式15]
在2mL乙腈中溶解2-(1-乙基磺酰基吲哚啉-2-基)-3-甲基-6-五氟乙基-3H-咪唑并[4,5-c]哒嗪(34.3mg,0.0743mmol),在冰冷却下加入N-氯代丁二酰亚胺(10.4mg,0.0780mmol),搅拌15分钟。升温至室温,搅拌15小时。在反应液中加入饱和碳酸氢钠水溶液及饱和硫代硫酸钠水溶液,使用乙酸乙酯进行提取,使用水及饱和食盐水进行清洗。使用无水硫酸钠对有机层进行干燥,蒸馏去除溶剂后,通过硅胶层析对得到的残渣进行提纯,得到2-(1-乙基磺酰基-5-氯吲哚啉-2-基)-3-甲基-6-五氟乙基-3H-咪唑并[4,5-c]哒嗪(27.4mg,75%)。
熔点:88-92℃
实施例3-1.
1-乙基磺酰基-N-(2-甲基氨基-5-三氟甲基吡啶-3-基)吲哚啉-2-甲酰胺的制备
[化学式16]
在6.5mL甲苯中溶解N-乙基磺酰基吲哚啉2-羧酸(0.335g,1.31mmol),在冰冷却下依次加入氯化亚砜(0.312g,2.62mmol)、0.5mL的N,N-二甲酰胺,加热回流1小时。放冷后,进行减压浓缩,得到N-乙基磺酰基吲哚啉2-甲酰氯。
在1.3mL四氢呋喃中溶解该甲酰氯(250mg,1.31mmol)及吡啶(0.311g,1.31mmol),在0℃下滴加3-氨基-2-甲基氨基-5-三氟甲基吡啶的四氢呋喃(2mL)溶液后,在室温下搅拌16小时。向反应液中加入氯化铵水溶液后,使用乙酸乙酯进行提取,使用水及饱和食盐水进行清洗。使用无水硫酸钠对有机层进行干燥,蒸馏去除溶剂后,通过硅胶层析对得到的残渣进行提纯,得到1-乙基磺酰基-N-(2-甲基氨基-5-三氟甲基吡啶-3-基)吲哚啉-2-甲酰胺(400mg,71%)。
熔点:176-178℃
实施例3-2.
2-(1-乙基磺酰基吲哚啉-2-基)-3-甲基-6-三氟甲基-3H-咪唑并[4,5-b]吡啶(化合物编号2-1)的制备
[化学式17]
在7mL的N-甲基-2-吡咯烷酮中,将实施例3-1中得到的1-乙基磺酰基-N-(2-甲基氨基-5-三氟甲基吡啶-3-基)吲哚啉-2-甲酰胺(300mg,0.700mmol)及对甲苯磺酸一水合物(400mg,2.10mmol)在150℃下加热搅拌2小时。放冷后,向反应液中加入饱和碳酸氢钠水溶液,使用乙酸乙酯进行提取,使用水及饱和食盐水对乙酸乙酯层进行清洗。使用无水硫酸钠对有机层进行干燥,蒸馏去除溶剂后,通过硅胶层析对得到的残渣进行提纯,得到2-(1-乙基磺酰基吲哚啉-2-基)-3-甲基-6-三氟甲基-3H-咪唑并[4,5-b]吡啶(52.1mg,18%)。
熔点:156-158℃
实施例4.
2-(1-乙基磺酰基吲哚啉-2-基)-5-三氟甲基硫代苯并[d]噁唑(化合物编号3-1)的制备
[化学式18]
在7mL的N-甲基-2-吡咯烷酮中,将根据实施例1-1的制备方法制备的1-乙基磺酰基-N-(2-羟基-5-三氟甲基硫代苯基)吲哚啉-2-甲酰胺(300mg,0.700mmol)及对甲苯磺酸一水合物(400mg,2.10mmol)在150℃下加热搅拌2小时。放冷后,向反应液中加入饱和碳酸氢钠水溶液,使用乙酸乙酯进行提取,使用水及饱和食盐水进行清洗。使用无水硫酸钠对有机层进行干燥,蒸馏去除溶剂后,通过硅胶层析对得到的残渣进行提纯,得到2-(1-乙基磺酰基吲哚啉-2-基)-5-三氟甲基硫代苯并[d]噁唑(52.1mg,18%)。
熔点:156-158℃
实施例5.
2-(1-乙基磺酰基-5-碘吲哚啉-2-基)-5-三氟甲基硫代苯并[d]噁唑(化合物编号3-5)的制备
[化学式19]
使用DIH来代替实施例2的制备方法的N-氯代丁二酰亚胺,以同样的方式进行制备。
熔点:136℃
实施例6.
2-(1-乙基磺酰基-5-环丙基吲哚啉-2-基)-5-三氟甲基硫代苯并[d]噁唑(化合物编号3-19)的制备
[化学式20]
在2.0mL甲苯及0.5mL水中溶解2-(1-乙基磺酰基-5-碘吲哚啉-2-基)-5-三氟甲基硫代苯并[d]噁唑(47.8mg,0.0862mmol)、环丙基硼酸(14.8mg,0.172mmol)、[1,1’-双(二苯基膦基)二茂铁]二氯化钯(II)(丙酮加成物)(6.56mg,0.00862mmol)及磷酸三钾(73.2mg,0.345mmol),在80℃下搅拌4小时。放冷后,向反应液中加入硅胶,减压浓缩,通过硅胶层析对得到的残渣进行提纯,得到2-(1-乙基磺酰基-5-环丙基吲哚啉-2-基)-5-三氟甲基硫代苯并[d]噁唑(24.2mg,60%)。
以下,示出制剂的实施例,但并不受其限定。制剂例中,份表示重量份。
制剂例1.
将以上物质均匀地混合溶解,制成乳剂。
制剂例2.
本发明化合物 3份
粘土粉末 82份
硅藻土粉末 15份
将以上物质均匀地混合粉碎,制成粉剂。
制剂例3.
本发明化合物 5份
膨润土与粘土的混合粉末 90份
木质素磺酸钙 5份
将以上物质均匀地混合,加入适量的水进行混炼、造粒、干燥,制成颗粒剂。
制剂例4.
本发明化合物 20份
高岭土与合成高分散硅酸 75份
聚氧乙烯壬基苯基醚与
烷基苯磺酸钙的混合物 5份
将以上物质均匀地混合粉碎,制成可湿性粉剂。
试验例1.
对桃蚜(Myzus persicae)的防除率试验
在直径8cm、高8cm的塑料盆中种植白菜,使桃蚜繁殖,调查各盆的寄生虫数。将本发明的通式(1)所表示的化合物或其盐类分散于水中,稀释成500ppm的药液,将该药液散布在盆植白菜的茎叶上,风干后,将盆保管于温室中,在散布药剂后第6天调查寄生在各个白菜上的桃蚜的寄生虫数,通过下述式计算防除率,通过下述判定标准进行判定。
[数学式1]
防除率=100-{(T×Ca)/(Ta×C)}×100
Ta:处理区的散布前寄生虫数
T:处理区的散布后寄生虫数
Ca:未处理区的散布前寄生虫数
C:未处理区的散布后寄生虫数
判定标准
A···防除率100%
B···防除率99%~90%
C···防除率89%~80%
D···防除率79%~50%
其结果,本发明化合物的1-39、1-41、1-43、1-45、1-60、1-77、1-78、2-1、2-3、2-4、2-5、2-6、2-21、2-40、3-1、3-3、3-4、3-5、3-6、3-19、3-21、3-45、3-79、3-80、3-81、3-82、3-83、3-84及3-85表现出A的活性。
试验例2.
对灰飞虱(Laodelphax striatella)的杀虫试验
将本发明的通式(1)所表示的缩合杂环化合物或其盐类分散于水中,稀释成500ppm的药液,将稻苗(品种:日本晴)在该药液中浸渍30秒,风干后,放入玻璃试管中,各接种10只三龄灰飞虱后,塞入棉栓,调查接种8天后的生死虫数,通过下述式计算校正死虫率,根据下述判定标准进行判定。
[数学式2]
校正死虫率
A···校正死虫率100%
B···校正死虫率99%~90%
C···校正死虫率89%~80%
D···校正死虫率79%~50%
其结果,本发明化合物的1-39、1-41、1-43、1-45、1-60、1-77、1-78、2-1、2-3、2-4、2-5、2-6、2-21、2-40、3-1、3-3、3-4、3-5、3-6、3-19、3-21、3-45、3-79、3-80、3-81、3-82、3-83、3-84及3-85表现出A的活性。
试验例3.对小菜蛾(Plutella xylostella)的杀虫试验
在白菜苗上放养小菜蛾的成虫,使其产卵,在放养2天后,将带有产下的卵的白菜苗在药液中浸渍约30秒,风干后,静置在25℃的恒温室中。所述药液为将以本发明的通式(1)所表示的吲哚啉化合物作为有效成分的药剂稀释成500ppm而成的药液。在该药液中浸渍6天后,调查孵化虫数,通过下述式计算出死虫率,按照试验例2的判定标准进行判定。1区10只重复3次。
[数学式3]
其结果,本发明化合物的1-39、1-41、1-43、1-45、1-60、1-77、1-78、2-1、2-3、2-4、2-5、2-6、2-21、2-40、3-1、3-3、3-4、3-5、3-6、3-19、3-21、3-45、3-79、3-80、3-81、3-82、3-83、3-84及3-85表现出A的活性。
工业实用性
本发明的化合物或其盐作为农业园艺用杀虫剂具有优异的效果。
Claims (6)
1.一种下述通式(1)所表示的吲哚啉化合物或其盐,
[化学式1]
通式(1)中,R1及R4可相同也可不同,其表示:(a1)氢原子;(a2)卤原子;(a3)(C1-C6)烷基;或(a4)(C1-C6)烷氧基,
R2及R3可相同也可不同,其表示:(b1)氢原子;(b2)卤原子;(b3)氰基;(b4)硝基;(b5)甲酰基;(b6)(C1-C6)烷基;(b7)(C3-C6)环烷基;(b8)(C1-C6)烷氧基;(b9)(C1-C6)烷氧基(C1-C6)烷基;(b10)卤代(C1-C6)烷基;(b11)卤代(C1-C6)烷氧基;(b12)(C1-C6)烷硫基;(b13)(C1-C6)烷基亚磺酰基;(b14)(C1-C6)烷基磺酰基;(b15)卤代(C1-C6)烷硫基;(b16)卤代(C1-C6)烷基亚磺酰基;(b17)卤代(C1-C6)烷基磺酰基;(b18)(C1-C6)烷氧基羰基;(b19)R8(R9)N基,其中,R8及R9可相同也可不同,其表示:氢原子、(C1-C6)烷基、(C2-C6)烯基、(C2-C6)炔基、(C3-C6)环烷基、(C3-C6)环烷基(C1-C6)烷基、(C1-C6)烷氧基(C1-C6)烷基、卤代(C1-C6)烷基、卤代(C1-C6)烷氧基(C1-C6)烷基、(C1-C6)烷基羰基、苯基或苯基(C1-C6)烷基;(c20)R8(R9)N羰基,其中,R8及R9与所述R8及R9相同;(b21)C(R8)=NOR9基,其中,R8及R9与所述R8及R9相同;(b22)苯基;(b23)在环上具有选自(a)卤原子、(b)氰基、(c)硝基、(d)甲酰基、(e)(C1-C6)烷基、(f)卤代(C1-C6)烷基、(g)(C1-C6)烷氧基、(h)卤代(C1-C6)烷氧基、(i)(C3-C6)环烷基(C1-C6)烷氧基、(j)(C1-C6)烷硫基、(k)卤代(C1-C6)烷硫基、(l)(C1-C6)烷基亚磺酰基、(m)卤代(C1-C6)烷基亚磺酰基、(n)(C1-C6)烷基磺酰基或(o)卤代(C1-C6)烷基磺酰基中的可相同也可不同的1~5个取代基的苯基;(b24)苯基(C1-C6)烷基;或(b25)在环上具有选自(a)卤原子、(b)氰基、(c)硝基、(d)甲酰基、(e)(C1-C6)烷基、(f)卤代(C1-C6)烷基、(g)(C1-C6)烷氧基、(h)卤代(C1-C6)烷氧基、(i)(C3-C6)环烷基(C1-C6)烷氧基、(j)(C1-C6)烷硫基、(k)卤代(C1-C6)烷硫基、(l)(C1-C6)烷基亚磺酰基、(m)卤代(C1-C6)烷基亚磺酰基、(n)(C1-C6)烷基磺酰基或(o)卤代(C1-C6)烷基磺酰基中的可相同也可不同的1~5个取代基的苯基(C1-C6)烷基,
R5可相同也可不同,其表示:(c1)卤代(C1-C6)烷基;(c2)卤代(C1-C6)烷氧基;(c3)卤代(C1-C6)烷硫基;(c4)卤代(C1-C6)烷基亚磺酰基;或(c5)卤代(C1-C6)烷基磺酰基,
Ra及Rb可相同也可不同,其表示:(d1)氢原子;(d2)卤原子;(d3)(C1-C6)烷基;(d4)(C1-C6)烷氧基;(d5)氰基;或(d6)(C1-C6)烷氧基羰基,或者Ra及Rb可结合形成3~6元的脂肪族环、或者Ra及Rb可与1个氧原子或硫原子键合,
Rc表示:(d1)氢原子;(d2)卤原子;(d3)(C1-C6)烷基;(d4)(C1-C6)烷氧基;或(d6)(C1-C6)烷氧基羰基,
A1及A2表示氮原子或C-R6,A3表示氧原子、硫原子或N-R7,其中,R6及R7可相同也可不同,其表示:(e1)氢原子;(e2)卤原子;(e3)氰基;(e4)硝基;(e5)(C1-C6)烷基;或(e6)(C1-C6)烷氧基,
m表示0、1或2,n表示1或2。
2.根据权利要求1所述的吲哚啉化合物或其盐,其中,
R1及R4可相同也可不同,其表示(a1)氢原子或(a2)卤原子,
R2及R3可相同也可不同,其表示:(b1)氢原子;(b2)卤原子;(b3)氰基;(b5)甲酰基;(b6)(C1-C6)烷基;(b7)(C3-C6)环烷基;(b8)(C1-C6)烷氧基;(b10)卤代(C1-C6)烷基;(b11)卤代(C1-C6)烷氧基;(b12)(C1-C6)烷硫基;(b15)卤代(C1-C6)烷硫基;(b18)(C1-C6)烷氧基羰基;(b19)R8(R9)N基,其中,R8及R9与所述R8及R9相同;(c20)R8(R9)N羰基,其中,R8及R9与所述R8及R9相同;或(b21)C(R8)=NOR9基,其中,R8及R9与所述R8及R9相同,
R5可相同也可不同,其表示:(c1)卤代(C1-C6)烷基;(c3)卤代(C1-C6)烷硫基;(c4)卤代(C1-C6)烷基亚磺酰基或(c5)卤代(C1-C6)烷基磺酰基,
Ra、Rb及Rc表示(d1)氢原子,
A1及A2表示氮原子或C-R6,A3表示氧原子、硫原子或N-R7,其中,R6及R7与所述R6及R7相同,
m表示2,n表示1。
3.根据权利要求1所述的吲哚啉化合物或其盐,其中,
R1及R4表示(a1)氢原子或(a2)卤原子;
R2及R3可相同也可不同,其表示:(b1)氢原子;(b2)卤原子;或(b7)(C3-C6)环烷基;(b10)卤代(C1-C6)烷基;或(b11)卤代(C1-C6)烷氧基,
R5可相同也可不同,其表示:(c1)卤代(C1-C6)烷基;或(c3)卤代(C1-C6)烷硫基;(c4)卤代(C1-C6)烷基亚磺酰基或(c5)卤代(C1-C6)烷基磺酰基,
Ra、Rb及Rc表示(d1)氢原子,
A1及A2表示氮原子或C-R6,A3表示氧原子或N-R7,其中,R6及R7与所述R6及R7相同,
m表示2,n表示1。
4.一种农业园艺用杀虫剂,其特征在于,其含有权利要求1~3中任一项所述的化合物作为有效成分。
5.一种农业园艺用杀虫剂的使用方法,其特征在于,以权利要求1~3中任一项所述的化合物的有效量对植物或土壤进行处理。
6.一种动物用的外部寄生虫防除剂,其特征在于,其含有权利要求1~3中任一项所述的化合物作为有效成分。
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- 2017-10-31 CN CN201780067658.6A patent/CN109906221B/zh not_active Expired - Fee Related
- 2017-10-31 JP JP2018549013A patent/JP6717968B2/ja not_active Expired - Fee Related
- 2017-10-31 US US16/345,931 patent/US10716306B2/en active Active
- 2017-10-31 EP EP17866908.1A patent/EP3539958A4/en not_active Withdrawn
- 2017-10-31 WO PCT/JP2017/039322 patent/WO2018084141A1/ja unknown
- 2017-10-31 BR BR112019008952A patent/BR112019008952A2/pt not_active Application Discontinuation
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CN115135384A (zh) * | 2019-11-28 | 2022-09-30 | 日本农药株式会社 | 苯并咪唑化合物或其盐类、和含有该化合物的农艺和园艺用杀虫杀螨剂以及其使用方法 |
CN115135384B (zh) * | 2019-11-28 | 2024-03-22 | 日本农药株式会社 | 苯并咪唑化合物或其盐类、和含有该化合物的农艺和园艺用杀虫杀螨剂以及其使用方法 |
CN115023426A (zh) * | 2020-01-06 | 2022-09-06 | 先正达农作物保护股份公司 | 具有含硫取代基的杀有害生物活性的杂环衍生物 |
Also Published As
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US10716306B2 (en) | 2020-07-21 |
CN109906221B (zh) | 2021-10-01 |
WO2018084141A1 (ja) | 2018-05-11 |
EP3539958A4 (en) | 2020-06-10 |
JPWO2018084141A1 (ja) | 2019-09-19 |
JP6717968B2 (ja) | 2020-07-08 |
US20200077659A1 (en) | 2020-03-12 |
EP3539958A1 (en) | 2019-09-18 |
BR112019008952A2 (pt) | 2019-07-09 |
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